Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(Arylidene)-N-benzene-sulfonyl-4-piperidone derivatives

research paper s

Synthesis, crystal structures and anti-inflammatory

activity of four 3,5-bis(arylidene)-N-benzene-

sulfonyl-4-piperidone derivatives

ISSN 2053-2296

Ning Li,^aXianyong Bai,^bLianshuang Zhang^band Yun Hou^b*

^aSchool of Pharmacy, Binzhou Medical University, Guanhai road 346, Yantai, Shandong 264003, People’s Republic of

China, and ^bSchool of Basic Medical Sciences, Binzhou Medical University, Guanhai road 346, Yantai, Shandong

264003, People’s Republic of China. *Correspondence e-mail: houyun820424@163.com

Received 4 July 2018

Accepted 17 September 2018

Edited by A. L. Spek, Utrecht University, The

Netherlands

3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and

anti-inﬂammatory activities because of their double ꢀ,ꢁ-unsaturated ketone

structural characteristics. If N-benzenesulfonyl substituents are introduced into

BAPs, the conﬁguration of the BAPs would change signiﬁcantly and their anti-

inﬂammatory activities should improve. Four N-benzenesulfonyl BAPs, namely

(3E,5E)-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(triﬂuoromethyl)benzylidene]-

piperidin-4-one dichloromethane monosolvate, C₂₈H₂₁F₆NO₃SꢀCH₂Cl₂, (4),

(3E,5E)-1-(4-ﬂuorobenzenesulfonyl)-3,5-bis[4-(triﬂuoromethyl)benzylidene]-

piperidin-4-one, C₂₇H₁₈F₇NO₃S, (5), (3E,5E)-1-(4-nitrobenzenesulfonyl)-3,5-

bis[4-(triﬂuoromethyl)benzylidene]piperidin-4-one, C₂₇H₁₈F₆N₂O₅S, (6), and

(3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis[4-(triﬂuoromethyl)benzylidene]pi-

peridin-4-one dichloromethane monosolvate, C₂₈H₁₈F₆N₂O₃SꢀCH₂Cl₂, (7), were

prepared by Claisen–Schmidt condensation and N-sulfonylation. They were

characterized by NMR, FT–IR and HRMS (high resolution mass spectrometry).

Single-crystal structure analysis reveals that the two 4-(triﬂuoromethyl)phenyl

rings on both sides of the piperidone ring in (4)–(7) adopt an E stereochemistry

of the oleﬁnic double bonds. Molecules of both (4) and (6) are connected by

hydrogen bonds into one-dimensional chains. In (5) and (7), pairs of adjacent

molecules embrace through intermolecular hydrogen bonds to form a

bimolecular combination, which are further extended into a two-dimensional

sheet. The anti-inﬂammatory activity data reveal that (4)–(7) signiﬁcantly inhibit

LPS-induced interleukin (IL-6) and tumour necrosis factor (TNF-ꢀ) secretion.

Most importantly, (6) and (7), with strong electron-withdrawing substituents,

display more potential inhibitory effects than (4) and (5).

Keywords: 3,5-bis(arylidene)-4-piperidone;

benzenesulfonyl; anti-inflammatory activity;

LPS-induced interleukin; tumour necrosis factor

secretion; inhibitory effects; crystal structure.

CCDC references: 1848378; 1848377;

1848376; 1848375

Supporting information: this article has

supporting information at journals.iucr.org/c

1. Introduction

Inﬂammation is an immune response to injury, tissue ischemia,

infectious agents and many pathological processes of chronic

diseases, especially, the development of tumours (Mantovani

et al., 2008; Medzhitov, 2010; Nieminen et al., 2010; Shin et al.,

2014). Epidemiological studies have shown that individuals

with ulcerative colitis may have a tenfold greater likelihood of

developing colorectal carcinoma (Hagemann et al., 2007).

Also, hepatocellular carcinoma (HCC) could slowly unfold

from chronic inﬂammation mainly triggered by exposure to

infectious agents or to toxic compounds (Berasain et al., 2009;

El-Serag & Rudolph, 2007). Therefore, anti-inﬂammation

plays a key role in the prevention of the development of

tumours.

Macrophages, an innate immune cell, can drive tumour

progression through the production of pro-inﬂammatory

mediators, such as interleukin 6 (IL-6) and tumour necrosis

factor-ꢀ (TNF-ꢀ), which are involved in the pathogenesis of

# 2018 International Union of Crystallography

Acta Cryst. (2018). C74, 1171–1179

https://doi.org/10.1107/S2053229618013232 1171

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tumours (Greten et al., 2004). Moreover, the expression of the

inﬂammatory cytokines, including IL-6 and TNF-ꢀ, can be

down-regulated by inhibiting the activation of free-radical-

activated transcription factors, such as transcription factor

nuclear factor-ꢂB (NF-ꢂB), which provides a critical link

between inﬂammation and tumour (Karin, 2009). It has been

observed that NF-ꢂB activation is a result of underlying

inﬂammation or a consequence of the formation of an

inﬂammatory microenvironment during tumour progression

(Chen et al., 2017). These observations suggest that NF-ꢂB is a

potential target for the design of new anticancer drugs with

anti-inﬂammatory activity.

cleavage of caspases 3/9 and PARP (Yadav et al., 2013).

Another alkylated monocarbonyl analogue of curcumin

(MAC 7a, Scheme 1) showed potent anti-inﬂammatory

activity against lipopolysaccharide (LPS)-induced acute lung

injury in rats by inhibiting the expression of IL-6, IL-1ꢁ,

TNF-ꢀ and vascular cell adhesion molecule (VCAM-1) in

Beas-2B cells (Zhu et al., 2016). N-Benzoyl BAP c6 (Scheme 1)

displayed potential anti-inﬂammatory activity by inhibiting

LPS-stimulated TNF-ꢀ, IL-6, IL-1ꢁ and nitric oxide produc-

tion in RAW 264.7 cells (Xie et al., 2017). Taken together,

BAPs possess excellent antitumour and anti-inﬂammatory

activities. More importantly, BAPs can be structurally modi-

ﬁed readily to potentially improve bioactivity, whereas

cucurmin is difﬁcult to modify.

Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-

dien-3,5-dione, see Scheme 1], a natural component of the

rhizome of Curcuma longa, has been proved to be a powerful

chemopreventive and antitumour agent with anti-inﬂamma-

tory, antibacterial and antioxidant properties. However, the

clinical use of curcumin has been limited because of its low

anticancer activity and poor bioavailability (Nelson et al.,

2017; Prakobwong et al., 2011). In order to overcome these

defects, many improved curcumin analogues have been

reported. 3,5-Bis(arylidene)-4-piperidone (BAP) derivatives

are analogues which display good antitumour and anti-

inﬂammatory activities. In BAPs, the 1,5-diaryl-3-oxopenta-

1,4-dienyl pharmacophore, with two ꢀ,ꢁ-unsaturated ketone

groups, shows signiﬁcant preference or sequential afﬁnity for

biothiols compared to amino and hydroxy groups, which

results in an improved chemosensitivity to tumour cells over

normal cells (Lagisetty et al., 2010; Das et al., 2010; Sun et al.,

2016; Li et al., 2017, 2018).

Recently, we have reported many novel symmetric and

unsymmetric BAPs (such as BAP 6d, see Scheme 1) as anti-

tumour agents (Li et al., 2015, 2018; Sun et al., 2016; Chen et al.,

2016; Liu et al., 2016; Yao et al., 2018). We hypothesize that by

changing the N-methyl substituent into N-benzenesulfonyl

substituents in BAPs, the conﬁguration of the BAPs would

change markedly and this might improve the antitumour and

anti-inﬂammatory activities of these compounds. In this study,

four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone deri-

3,5-Bis(2-ﬂuorobenzylidene)-4-piperidone (EF24, Scheme 1)

is an effective antitumour agent that inhibits tumour growth

and metastasis by inhibiting NF-ꢂB-dependent signalling

pathways (Yin et al., 2016) or IKKꢁ kinase activity (Kasinski et

al., 2008), inducing G2/M arrest and apoptosis (Selvendiran et

al., 2007). CLEFMA (Scheme 1) can induce apoptosis by

ꢁ

1172 Li et al. 3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

Acta Cryst. (2018). C74, 1171–1179

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Table 1

Experimental details.

(4)

(5)

(6)

(7)

Crystal data

Chemical formula

M_r

C₂₈H₂₁F₆NO₃SꢀCH₂Cl₂

650.44

C₂₇H₁₈F₇NO₃S

569.48

C₂₇H₁₈F₆N₂O₅S

596.49

C₂₈H₁₈F₆N₂O₃SꢀCH₂Cl₂

661.43

Crystal system, space group

Temperature (K)

Monoclinic, P2₁/n

150

8.6718 (5), 23.5083 (12),

14.3939 (9)

90, 102.962 (2), 90

Triclinic, P1

150

8.5664 (6), 10.0932 (8),

14.3871 (12)

90.590 (4), 98.592 (4),

97.309 (4)

1219.44 (17)

2

Mo Kꢀ

0.22

Triclinic, P1

150

7.4346 (7), 11.6714 (11),

14.6479 (15)

90.825 (5), 96.884 (5),

98.971 (5)

1245.7 (2)

2

Mo Kꢀ

0.22

Triclinic, P1

150

9.7338 (6), 12.4558 (9),

12.6397 (9)

70.586 (3), 88.379 (4),

81.726 (3)

1429.97 (17)

2

Mo Kꢀ

0.38

˚

a, b, c (A)

ꢀ, ꢁ, ꢄ (^ꢄ)

3

˚

V (A )

2859.6 (3)

4

Mo Kꢀ

0.37

Z

Radiation type

ꢅ (mm^ꢂ1

Crystal size (mm)

)

0.14 ꢅ 0.10 ꢅ 0.10

0.26 ꢅ 0.17 ꢅ 0.10

0.18 ꢅ 0.16 ꢅ 0.10

0.20 ꢅ 0.15 ꢅ 0.11

Data collection

Diffractometer

Bruker SMART CCD

area detector

Bruker SMART CCD

area detector

21256, 4790, 3187

Bruker SMART CCD

area detector

23092, 4848, 3350

Bruker SMART CCD

area detector

24790, 5604, 3869

No. of measured, independent 38920, 5852, 4236

and observed [I > 2ꢆ(I)]

reﬂections

R_int

0.062

0.626

0.074

0.617

0.072

0.617

0.070

0.617

ꢂ1

˚

(sin ꢇ/ꢈ)_max(A

)

Reﬁnement

R[F²> 2ꢆ(F²)], wR(F²), S

No. of reﬂections

No. of parameters

0.047, 0.126, 1.04

5852

408

0.050, 0.129, 1.01

4790

380

0.051, 0.129, 1.03

4848

370

0.046, 0.109, 1.01

5604

388

H-atom treatment

H-atom parameters

constrained

0.69, ꢂ0.65

H-atom parameters

constrained

0.48, ꢂ0.38

H-atom parameters

constrained

0.41, ꢂ0.41

H-atom parameters

constrained

0.53, ꢂ0.44

ꢂ3

˚

Áꢉ_max, Áꢉ_min(e A

)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2012), SHELXT2014 (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b) and SHELXTL (Sheldrick, 2008).

vatives, i.e. (4)–(7), were synthesized (Scheme 2) and their

structures conﬁrmed by single-crystal X-ray diffraction.

ture (RT) for about 24 h [monitored by thin-layer chromato-

graphy (TLC)], the precipitates were collected and washed

with acetone to obtain intermediate (3). (3) (0.45 g, 1.0 mmol)

and benzenesulfonyl chloride [4-toluenesulfonyl chloride

(0.21 g, 1.1 mmol), 4-ﬂuorobenzenesulfonyl chloride (0.21 g,

1.1 mmol), 4-nitrobenzenesulfonyl chloride (0.24 g, 1.1 mmol)

or 4-cyanobenzenesulfonyl chloride (0.22 g, 1.1 mmol) for (4)–

(7), respectively] were dissolved in dichloromethane (20 ml).

Two drops of pyridine were added to the mixture, which was

then stirred for about 6 h at RT (monitored by TLC). The

precipitates were collected, washed with water and recrys-

tallized from dichloromethane/petroleum ether (1:1 v/v) as

light-yellow powders of (4)–(7). Single crystals were prepared

by slow evaporation of dichloromethane/methanol solutions

of (4)–(7) at RT.

2.2.1. Analytical data for (4). Light-yellow powder; yield:

81%; m.p. 465ꢃ467 K. IR (cm^ꢂ1): 1674 (m), 1614 (s), 1394 (m),

1325 (s), 1261 (m), 1243 (s), 1161 (s), 1088 (m), 1069 (s), 1037

(m), 1016 (s), 986 (s), 840 (s), 804 (m), 765 (m), 738 (s), 694 (s),

672 (s). ¹H NMR (600 MHz, DMSO-d₆): ꢃ 7.88 (d, J = 8.0 Hz,

4H), 7.71 (d, J = 7.9 Hz, 4H), 7.65 (s, 2H), 7.44 (d, J = 7.9 Hz,

2H), 7.37 (d, J = 7.9 Hz, 2H), 4.64 (s, 4H), 2.41 (s, 3H). ¹³C

NMR (150 MHz, DMSO-d₆): ꢃ 21.0, 46.5, 124.0 (q, J =

270.6 Hz, CF₃), 125.6 (q, J = 5.6 Hz, 2C-CF₃), 127.2, 129.3 (q,

J = 32.2 Hz, 1C-CF₃), 129.9, 130.9, 132.5, 134.2, 135.6, 137.9,

144.1, 184.0. HRMS (FTMS) calculated for C₂₈H₂₂F₆NO₃S

[M + H⁺] 566.1225, found 566.1229.

2. Experimental

2.1. Chemistry

4-(Triﬂuoromethyl)benzaldehyde, (1), 4-piperidone hydrate

hydrochloride, (2), 4-ﬂuorobenzenesulfonyl chloride, 4-nitro-

benzenesulfonyl chloride and 4-cyanobenzenesulfonyl

chloride were purchased from Sinopharm Chemical Reagent

Co. Ltd (Shanghai, China). ¹H NMR data were collected using

a Bruker Avance 400 MHz spectrometer. ¹³C NMR data were

collected at 100 MHz on a Bruker Avance 400 MHz spec-

trometer or at 150 MHz on a Bruker Avance 600 MHz spec-

trometer. Chemical shifts were reported in ꢃ relative to TMS

(tetramethylsilane). HRMS (FTMS) were performed on a

Finnigan-MAT-95 mass spectrometer. IR spectra were

obtained in the 400–4000 cm^ꢂ1range using a PerkinElmer

Frontier Mid-IR FT–IR spectrometer.

2.2. Synthesis and crystallization of (4)–(7)

4-(Triﬂuoromethyl)benzaldehyde, (1) (1.74 g, 10.0 mmol),

and 4-piperidone hydrate hydrochloride, (2) (0.77 g,

5.0 mmol), were dissolved in acetic acid (10 ml). Dry hydrogen

chloride gas was passed through this mixture for 35 min and a

clear solution was obtained. After stirring at room tempera-

ꢁ

Acta Cryst. (2018). C74, 1171–1179

Li et al.

3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives 1173

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2.2.2. Analytical data for (5). Light-yellow powder; yield:

83%; m.p. 515–517 K. IR (cm^ꢂ1): 1674 (s), 1615 (s), 1585 (m),

1529 (s), 1371 (m), 1321 (s), 1261 (m), 1238 (m), 1169 (s), 1113

(s), 1069 (s), 1041 (m), 1015 (m), 992 (m), 968 (m), 937 (m), 848

1

(s), 827 (s), 770 (m), 735 (s), 698 (m). H NMR (400 MHz,

DMSO-d₆): ꢃ 7.89 (d, J = 8.3 Hz, 4H), 7.73 (d, J = 8.1 Hz, 4H),

7.64 (s, 2H), 7.59 (m, 2H), 7.41 (m, 2H), 4.70 (s, 4H). ¹³C NMR

(100 MHz, DMSO-d₆): ꢃ 47.3, 117.4 (d, ²J_CF= 22.4 Hz), 124.7

(q, J = 271.4 Hz, CF₃), 126.4 (q, J = 3.2 Hz, 2C-CF₃), 130.1 (q,

3

J = 32.6 Hz, 1C-CF₃), 131.2 (d, J_CF= 9.6 Hz), 131.8, 133.0,

134.5 (d, ⁴J_CF= 2.8 Hz), 136.5, 138.6, 165.5 (d, ¹J_CF= 251.2 Hz),

184.7. HRMS (FTMS) calculated for C₂₇H₁₉F₇NO₃S [M + H⁺]

570.0974, found 570.0972.

Figure 1

A

perspective view of (4), showing the atom-labelling scheme.

Displacement ellipsoids are drawn at the 50% probability level.

Disordered atoms F4⁰, F5⁰and F6⁰in the triﬂuoromethyl group have

been omitted for clarity, as has the dichloromethane solvent molecule.

2.2.3. Analytical data for (6). Light-yellow powder; yield:

86%; m.p. 518–520 K. IR (cm^ꢂ1): 1673 (s), 1613 (s), 1589 (s),

1327 (s), 1242 (s), 1188 (m), 1163 (s), 1113 (s), 1086 (m), 1071

(s), 1038 (s), 1016 (s), 986 (s), 942 (m), 847 (s), 818 (m), 803 (s),

738 (s). ¹H NMR (400 MHz, DMSO-d₆): ꢃ 8.38 (d, J = 9.2 Hz,

2H), 7.89 (d, J = 8.3 Hz, 4H), 7.81 (d, J = 9.2 Hz, 2H), 7.74 (d, J

= 8.2 Hz, 4H), 7.65 (s, 2H), 4.75 (s, 4H). ¹³C NMR (100 MHz,

DMSO-d₆): ꢃ 47.3, 124.7 (q, J = 270.7 Hz, CF₃), 125.5, 126.4 (q,

J = 3.7 Hz, C-CF₃), 129.6, 130.2 (q, J = 31.7 Hz, C-CF₃), 131.8,

132.7, 136.9, 138.5, 143.6, 150.8, 184.7. HRMS (FTMS) calcu-

lated for C₂₇H₁₉F₆N₂O₅S [M + H⁺] 597.0919, found 597.0923.

2.2.4. Analytical data for (7). Light-yellow powder; yield:

81%; m.p. 496–498 K. IR (cm^ꢂ1): 2237 (s), 1675 (s), 1614 (s),

1414 (m), 1369 (s), 1322 (s), 1266 (m), 1239 (m), 1169 (s), 1113

(m), 1068 (s), 1042 (s), 1016 (s), 992 (s), 936 (s), 829 (s), 742

kit (eBioScience, CA, USA). Brieﬂy, RAW264.7 cells were

pretreated with 30 mM of pyrrolidinedithiocarbamate (PDTC)

or with 10 mM of compounds for 2 h. After treatment with

LPS (1 mg ml^ꢂ1) for 22 h, the culture media were centrifuged

and collected. The optical density was determined using a

Thermo Multiskan FC at 450 nm (Thermo Scientiﬁc, MA,

USA).

3. Results and discussion

3.1. Synthetic analysis

The title compounds (4)–(7) were synthesized using stan-

dard protocols for Claisen–Schmidt condensation and N-sul-

fonylation. The synthetic strategy and structures of (4)–(7) are

shown in Scheme 2. The Claisen–Schmidt condensation

reaction was catalyzed by dry HCl. The harvested inter-

mediate (3) was stable at room temperature. The N-sulfonyl-

ation reaction was catalyzed by pyridine. The target com-

pounds were ﬁltered off, washed with water and recrystallized

from dichloromethane/petroleum ether. The overall yields of

(4)–(7) were more than 80%, because there were symmetric

products as opposed to dissymmetric BAPs (Li et al., 2018).

1

(m), 699 (s). H NMR (400 MHz, DMSO-d₆): ꢃ 8.07 (m, 2H),

7.89 (d, J = 8.4 Hz, 4H), 7.73 (d, J = 8.4 Hz, 4H), 7.68 (m, 2H),

7.62 (s, 2H), 4.74 (s, 4H). ¹³C NMR (100 MHz, DMSO-d₆): ꢃ

47.3, 116.6, 118.3, 124.7 (q, J = 271.2 Hz, CF₃), 126.4 (q, J =

3.7 Hz, 2C-CF₃), 128.7, 130.1 (q, J = 31.8 Hz, 1C-CF₃), 131.8,

132.7, 134.3, 136.7, 138.5, 142.3, 184.7. HRMS (FTMS) calcu-

lated for C₂₈H₁₉F₆N₂O₃S [M + H⁺] 577.1021, found 577.1024.

2.3. Refinement

Crystal data, data collection and structure reﬁnement

details are summarized in Table 1. The methylene H atoms of

(4)–(7) and the methyl H atoms of (4) were placed in

geometrically idealized positions and constrained to ride on

3.2. Structural characterization

1

The structures of (4)–(7) were fully characterized by H

NMR, ¹³C NMR, FT–IR and HRMS (high resolution mass

˚

their parent C atoms, with C—H = 0.99 A and U_iso(H) =

˚

1.2U_eq(C) for methylene, and C—H = 0.98 A and U_iso(H) =

1.5U_eq(C) for methyl H atoms. In (4), the triﬂuoromethyl

groups were disordered, with reﬁned site-occupation factors of

0.51 (3) and 0.49 (3) for atoms F4/F5/F6 and F4⁰/F5⁰/F6⁰,

respectively. In (5), the triﬂuoromethyl groups were disor-

dered, with reﬁned site-occupation factors of 0.532 (19) and

0.458 (19) for atoms F1/F2/F3 and F1⁰/F2⁰/F3⁰, respectively.

Geometric restraints in (4) and (5) were used for modelling

the triﬂuoromethyl-group disorder.

2.4. Anti-inflammatory evaluation of (4)–(7)

Figure 2

A

perspective view of (5), showing the atom-labelling scheme.

The anti-inﬂammatory effects of compounds (4)–(7) were

evaluated by inhibition of TNF-ꢀ and IL-6 secretion from

RAW264.7 macrophages stimulated by LPS using an ELISA

Displacement ellipsoids are drawn at the 50% probability level.

Disordered atoms F1⁰, F2⁰and F3⁰in the triﬂuoromethyl group have

been omitted for clarity.

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1174 Li et al. 3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

Acta Cryst. (2018). C74, 1171–1179

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ring. Based on the ¹³C NMR data, a carbonyl C atom can be

found around 184 ppm.

From the FT–IR spectral data, the characteristic band at

1673ꢃ1675 cm^ꢂ1is attributed to the stretching vibration of the

C

O group of piperidone in (4)–(7). The strong bands at

1615ꢃ1613 cm^ꢂ1are due to the stretching vibration of the

C

C group in the ꢀ,ꢁ-unsaturated ketone. The strong bands

at 1169ꢃ1161 cm^ꢂ1are attributed to the sulfonamide group

(–SO₂N-). In addition, the presence of a cyano group (CN) in

(7) can be conﬁrmed by the characteristic bands at around

2237 cm^ꢂ1(stretching vibration of –CN). Additionally, HRMS

further conﬁrmed the molecular weights and are consistent

with the calculated results.

Figure 3

A perspective view of (6), showing the atom-labelling scheme.

Displacement ellipsoids are drawn at the 50% probability level.

3.3. Crystal structure analysis

Single-crystal structure analysis shows that (4) crystallizes in

the monoclinic space group P2₁/n, while (5)–(7) crystallize in

the triclinic space group P1. The asymmetric units of (4)–(7)

contain one drug molecule each (Figs. 1–4). The main frame-

work consists of 3,5-bis(arylidene)-N-benzenesulfonyl-4-

piperidone with different substituents (–CH₃, –F, –NO₂and

–CN) on the N-benzenelfonyl group, resulting in signiﬁcantly

different molecular conﬁgurations.

The four molecules (4)–(7) are similar in that both sides of

the 3,5-bis(arylidene)-4-piperidone ring expand in a linear

fashion, with the two 4-(triﬂuoromethyl)phenyl rings adopting

an E stereochemistry of the oleﬁnic double bonds and thus the

E,E isomer (Li et al., 2018; Sun et al., 2016). In addition, the

values of the ꢇ(C2—C6—C7—C12) and ꢇ(C4—C14—C15—

C20) torsion angles show similar structural features, which

may assist in gleaning further knowledge of the structural

features inﬂuencing cytotoxicity (Dimmock et al., 2002). The

ꢇ(C2—C6—C7—C12) and ꢇ(C4—C14—C15—C20) torsion

angles are ꢂ32.9 (4) and 29.5 (4)^ꢄin (4), ꢂ30.2 (5) and

30.7 (4)^ꢄin (5), 30.2 (4) and ꢂ27.5 (5)^ꢄin (6), and ꢂ28.6 (4)

and 32.8 (4)^ꢄin (7), respectively. The dihedral angle between

the two 4-(triﬂuoromethyl)phenyl rings is 24.1 (3)^ꢄin (4),

Figure 4

A

perspective view of (7), showing the atom-labelling scheme.

Displacement ellipsoids are drawn at the 50% probability level. The

dichloromethane solvent molecule has been omitted for clarity.

1

spectrometry). Based on the H NMR data, there is only an

evident unimodal signal in the range 7.65ꢃ7.62 ppm, corre-

sponding to the proton signals of –C CH– in the ꢀ,ꢁ-unsa-

turated ketone. Meanwhile, there is only a distinct unimodal

signal in the range 4.75ꢃ4.64 ppm, corresponding to the

proton signals of the –CH₂groups of the central piperidone

Figure 5

(a) The one-dimensional chain formed through intermolecular hydrogen bonds in (4). (b) The detailed hydrogen bonding, indicated by dashed lines. The

4-(triﬂuoromethyl)benzylidene groups have been omitted for clarity. [Symmetry codes: (i) ꢂx + 1, ꢂy, ꢂz; (ii) ꢂx, ꢂy, ꢂz; (iii) x + 1, y, z.]

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3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives 1175

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Table 2

Hydrogen-bond geometry (A, ) for (4).

group adopts a pseudo-equatorial conformation, with C2—

C1—N1—S1 = 154.2 (2)^ꢄin (6) and 149.8 (2)^ꢄin (7). As shown

in Figs. 1 and 2, (4) or (5) look like an ‘organic clip’ (Hou et al.,

2012). This could be caused by the different substituents of the

N-benzenesulfonyl group and the packing.

As shown in Fig. 5, the molecular units of (4) are connected

by intermolecular C—Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀCl hydrogen bonds

into a one-dimensional antiparallel double chain which

extends along the crystallographic a axis (Fig. 5a). Relevant

hydrogen-bonding geometries are given in Table 2. As a

hydrogen-bonding donor and acceptor, the dichloromethane

solvent molecule plays an important role in the formation of

the chain and links three BAP molecules through three

hydrogen bonds (Table 2 and Fig. 5b).

ꢄ

˚

D—Hꢀ ꢀ ꢀA

D—H

Hꢀ ꢀ ꢀA

Dꢀ ꢀ ꢀA

D—Hꢀ ꢀ ꢀA

C1—H1Aꢀ ꢀ ꢀO1ⁱ

C1—H1Aꢀ ꢀ ꢀO2ⁱⁱ

C5—H5Bꢀ ꢀ ꢀCl1ⁱ

C29—H29Aꢀ ꢀ ꢀO1

C29—H29Aꢀ ꢀ ꢀO2ⁱⁱⁱ

0.99

2.53

2.61

2.98

2.34

2.60

3.390 (3)

3.365 (3)

3.832 (2)

3.279 (3)

3.162 (3)

145

133

144

159

116

Symmetry codes: (i) ꢂx þ 1; ꢂy; ꢂz; (ii) ꢂx; ꢂy; ꢂz; (iii) x þ 1; y; z.

18.6 (2)^ꢄin (5), 7.0 (2)^ꢄin (6) and 15.0 (2)^ꢄin (7), the dihedral

angle in (6) being slightly smaller than the others.

The four structures differ markedly in the conformation of

the N-arylsulfonyl groups. In (4) and (5), the arylsulfonyl

group adopts a pseudo-axial conformation with respect to the

4-pyridone ring, with C2—C1—N1—S1 = ꢂ88.3 (2)^ꢄin (4) and

89.4 (2)^ꢄin (5), with the arylsulfonyl ring endo with respect to

the 4-pyridone ring. In contrast, in (6) and (7), the arylsulfonyl

As shown in Fig. 6(a), adjacent BAP molecules in (5) are

joined through intermolecular C26—H26ꢀ ꢀ ꢀO1ⁱhydrogen

bonds to generate a bimolecular macrocycle, from which four

4-(triﬂuoromethyl)benzylidene groups extend. Based on the

Figure 6

(a) The bimolecular macrocycle formed through intermolecular C26–H26ꢀ ꢀ ꢀO1ⁱhydrogen bonds in (5). (b) A top view of the bimolecular macrocycle. (c)

The two-dimensional network linked by C1—H1Bꢀ ꢀ ꢀO1ⁱⁱⁱand C23—H23ꢀ ꢀ ꢀF1ⁱⁱhydrogen bonds, indicated by dashed lines. Disordered atoms F1⁰, F2⁰

and F3⁰have been omitted for clarity. [Symmetry codes: (i) ꢂx + 1, ꢂy, ꢂz; (ii) ꢂx + 1, ꢂy + 1, ꢂz + 1; (iii) ꢂx + 1, ꢂy + 1, ꢂz.]

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1176 Li et al. 3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

Acta Cryst. (2018). C74, 1171–1179

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Figure 7

(a) The one-dimensional chain formed through intermolecular hydrogen bonds in (6). (b) The detailed hydrogen bonding, indicated by dashed lines. The

3,5-bis[4-(triﬂuoromethyl)benzylidene]piperidin-4-one groups have been omitted for clarity. [Symmetry codes: (i) ꢂx + 1, ꢂy + 1, ꢂz + 2; (ii) x + 1, y, z.]

Figure 8

(a) The bimolecular macrocycle formed through intermolecular C27—H27ꢀ ꢀ ꢀO3ⁱⁱhydrogen bonds in (7). (b) The two-dimensional network linked by

hydrogen bonds between molecules of dichloromethane and BAP in (7). The 4-(triﬂuoromethyl)benzylidene groups have been omitted for clarity.

Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) ꢂx + 1, ꢂy + 1, ꢂz + 1; (ii) ꢂx, ꢂy + 2, ꢂz + 1; (iii) ꢂx, ꢂy + 1, ꢂz + 1.]

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3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives 1177

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Table 3

Hydrogen-bond geometry (A, ) for (5).

Table 5

Hydrogen-bond geometry (A, ) for (7).

ꢄ

˚

D—Hꢀ ꢀ ꢀA

D—H

Hꢀ ꢀ ꢀA

Dꢀ ꢀ ꢀA

D—Hꢀ ꢀ ꢀA

D—H

Hꢀ ꢀ ꢀA

Dꢀ ꢀ ꢀA

D—Hꢀ ꢀ ꢀA

C26—H26ꢀ ꢀ ꢀO1ⁱ

0.95

0.99

2.58

2.61

2.46

3.458 (3)

3.364 (12)

3.242 (7)

3.293 (3)

154

140

124

142

C29—H29Bꢀ ꢀ ꢀO1

C29—H29Aꢀ ꢀ ꢀO2ⁱ

C27—H27ꢀ ꢀ ꢀO3ⁱⁱ

C5—H5Aꢀ ꢀ ꢀCl1ⁱⁱⁱ

0.99

0.95

0.99

2.57

2.53

2.48

2.81

3.342 (4)

3.500 (4)

3.362 (3)

3.776 (3)

135

166

155

166

ii

C23—H23ꢀ ꢀ ꢀF2⁰

C23—H23ꢀ ꢀ ꢀF1ⁱⁱ

C1—H1Bꢀ ꢀ ꢀO1ⁱⁱⁱ

Symmetry codes: (i) ꢂx þ 1; ꢂy; ꢂz; (ii) ꢂx þ 1; ꢂy þ 1; ꢂz þ 1; (iii) ꢂx þ 1,

Symmetry codes: (i) ꢂx þ 1; ꢂy þ 1; ꢂz þ 1; (ii) ꢂx; ꢂy þ 2; ꢂz þ 1; (iii) ꢂx; ꢂy þ 1,

ꢂy þ 1; ꢂz.

ꢂz þ 1.

Table 4

Hydrogen-bond geometry (A, ) for (6).

ꢄ

˚

solvent molecule plays a key role in the crystal packing. Two

hydrogen-bonding donors (C—H) are joined to two groups of

bimolecular combination through C29—H29Bꢀ ꢀ ꢀO1 and

C29—H29Aꢀ ꢀ ꢀO2ⁱhydrogen bonds. Meanwhile, the hydro-

gen-bonding acceptor (Cl atom) links to a third bimolecular

combination via C5—H5Aꢀ ꢀ ꢀCl1ⁱⁱⁱhydrogen bonds. The

bimolecular combinations are thus extended into a two-

dimensional network (Fig. 8b). Relevant hydrogen-bonding

geometries and symmetry codes are given in Table 5.

The distinct structural features of the four title compounds

are the different substituents (–CH₃, –F, –NO₂and –CN) on

the N-benzenesulfonyl group of (4)–(7). These substituents do

not play a major role in the hydrogen-bonding patterns and

crystal packing. However, their electron-donating or electron-

withdrawing effect may inﬂuence biological activity.

D—Hꢀ ꢀ ꢀA

D—H

Hꢀ ꢀ ꢀA

Dꢀ ꢀ ꢀA

D—Hꢀ ꢀ ꢀA

C24—H24ꢀ ꢀ ꢀO3ⁱ

0.95

2.56

2.36

3.380 (4)

3.304 (3)

145

176

C23—H23ꢀ ꢀ ꢀO2ⁱⁱ

Symmetry codes: (i) x þ 1; y; z; (ii) ꢂx þ 1; ꢂy þ 1; ꢂz þ 2.

top view in Fig. 6(b), an open elliptic capsule exists, where the

i

˚

O1ꢀ ꢀ ꢀO1 separation is 5.390 (3) A and the S1ꢀ ꢀ ꢀS1 separation

˚

is 11.134 (1) A. In the solid state, as shown in Fig. 6(c), the

bimolecular macrocycles are linked into a two-dimensional

sheet by C1—H1Bꢀ ꢀ ꢀO1ⁱⁱⁱand C23—H23ꢀ ꢀ ꢀF1ⁱⁱhydrogen

bonds (see Table 3 for details and symmetry codes).

In (6), a one-dimensional chain is generated by inter-

molecular hydrogen bonds which extends in the crystal-

lographic a-axis direction (Fig. 7a). 3,5-Bis[4-(triﬂuoro-

methyl)benzylidene]piperidin-4-one units are embedded in

both sides of the one-dimensional chain via N—S bonds. For

clarity, these units are omitted in Fig. 7(b). The chain looks

like a planar ribbon. An R₂²(10) motif and an R⁴₄(14) motif are

formed from C23—H23ꢀ ꢀ ꢀO2ⁱⁱand C24—H24ꢀ ꢀ ꢀO3ⁱhydrogen

bonds (Etter, 1990). Relevant hydrogen-bonding geometries

and symmetry codes are given in Table 4.

As shown in Fig. 8(a), and different from (5), two BAP

molecules of (7) are joined together via intermolecular C27—

H27ꢀ ꢀ ꢀO3ⁱⁱhydrogen bonds to generate a bimolecular

combination without a macrocycle. An R²₂(10) motif can be

found in the bimolecular combination. The dichloromethane

3.4. Anti-inflammatory activity

LPS is a main component of Gram-negative bacterial

endotoxin and can directly activate macrophages to secrete

pro-inﬂammatory cytokines, such as TNF-ꢀ and IL-6 (Singh et

al., 2017). In our study, (4)–(7) had no signiﬁcant toxicity at

10 mM on RAW264.7 cells (Fig. 9). The effect of the four

compounds on IL-6 and TNF-ꢀ secretion in RAW264.7 cells

stimulated by LPS was detected by ELISA. PDTC was used as

a reference standard. After treatment with (4)–(7), the

secretion of IL-6 and TNF-ꢀ was signiﬁcantly decreased with a

35–70% inhibition rate at a concentration of 10 mM compared

with only LPS-stimulated cells; the inhibitory effects are

Figure 9

(a) IL-6 expression levels in the culture media measured by ELISA. (b) TNF-ꢀ expression levels in the culture media tested by ELISA. PDTC was used

as a positive control. The results were presented as the percent of LPS control. Each bar represents the mean ꢆSD of three independent experiments.

Statistical signiﬁcance relative to the LPS group is indicated: (*) p < 0.05; (**) p < 0.01.

ꢁ

1178 Li et al. 3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

Acta Cryst. (2018). C74, 1171–1179

research papers

Kasinski, A. L., Du, Y ., Thomas, S. L., Zhao, J., Sun, S. Y., Khuri, F. R.,

Wang, C. Y., Shoji, M., Sun, A., Snyder, J. P ., Liotta, D. & Fu, H.

(2008). Mol. Pharmacol. 74 , 654–661.

Lagisetty, P ., Vilekar, P ., Sahoo, K., Anant, S. & Awasthi, V . (2010).

Bioorg. Med. Chem. Lett. 18 , 6109–6120.

superior to PDTC. In particular, (6) and (7), with strong

electron-withdrawing substitutes (–NO₂and –CN), lead to a

signiﬁcant inhibitory effect against both TNF-ꢀ and IL-6

secretion compared with (4), having an electron-donating

group (–CH₃), and (5), having a weak electron-withdrawing

substituent (–F).

Li, H. J., Wang, L., Zhao, J. J., Sun, J. F., Sun, J. L., Wang, C. H. & Hou,

G. G. (2015). J. Mol. Struct. 1079 , 414–422.

Li, N., Xin, W . Y ., Yao, B. R., Wang, C. H., Cong, W., Zhao, F., Li, H. J.,

Hou, Y ., Meng, Q. G. & Hou, G. G. (2018). Eur. J. Med. Chem. 147 ,

21–33.

Funding information

Li, N., Yao, B., Wang, C., Meng, Q. & Hou, G. (2017). Acta Cryst. C 73 ,

1003–1009.

Funding for this research was provided by: National Natural

Science Foundation of China (grant No. 81601049); Natural

Science Foundation of Shandong Province (grant Nos.

ZR2016HP05 and ZR2016HL24); Shandong Province Higher

Educational Science and Technology Program (project No.

J16LK01); Binzhou Medical University (project No.

BY2014KYQD07).

Liu, L. D., Liu, S. L., Liu, Z. X. & Hou, G. G. (2016). . J. Mol. Struct.

1112 , 1–8.

Mantovani, A., Allavena, P ., Sica, A. & Balkwill, F . (2008). Nature ,

454 , 436–444.

Medzhitov, R. (2010). Cell , 140 , 771–776.

Nelson, K. M., Dahlin, J. L., Bisson, J., Graham, J., Pauli, G. F . &

Walters, M. A. (2017). J. Med. Chem. 60 , 1620–1637.

Nieminen, R., Korhonen, R., Moilanen, T., Clark, A. R. & Moilanen,

E. (2010). Arthritis Rheum. 62 , 1650–1659.

Prakobwong, S., Khoontawad, J., Yongvanit, P ., Pairojkul, C., Hiraku,

Y ., Sithithaworn, P ., Pinlaor, P ., Aggarwal, B. B. & Pinlaor, S. (2011).

J. Int. Cancer , 129 , 88–100.

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Acta Cryst. (2018). C74, 1171–1179

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3,5-Bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives 1179

supporting information

Acta Cryst. (2018). C74, 1171-1179 [https://doi.org/10.1107/S2053229618013232]

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(aryl-

idene)-N-benzenesulfonyl-4-piperidone derivatives

Ning Li, Xianyong Bai, Lianshuang Zhang and Yun Hou

Computing details

For all structures, data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT

(Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine

structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare

material for publication: SHELXTL (Sheldrick, 2008).

(3E,5E)-1-(4-Fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane

monosolvate (4)

Crystal data

C₂₈H₂₁F₆NO₃S·CH₂Cl₂

M_r= 650.44

F(000) = 1328

D_x= 1.511 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 9943 reflections

θ = 2.5–26.4°

Monoclinic, P2₁/n

a = 8.6718 (5) Å

b = 23.5083 (12) Å

c = 14.3939 (9) Å

β = 102.962 (2)°

V = 2859.6 (3) Å³

Z = 4

µ = 0.37 mm⁻¹

T = 150 K

Block, yellow

0.14 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area detector

diffractometer

4236 reflections with I > 2σ(I)

R_int= 0.062

Radiation source: sealed tube

phi and ω scans

38920 measured reflections

5852 independent reflections

θ_max= 26.4°, θ_min= 2.3°

h = −10→10

k = −29→29

l = −17→17

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.047

wR(F²) = 0.126

S = 1.04

5852 reflections

408 parameters

0 restraints

Hydrogen site location: inferred from

neighbouring sites

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0541P)²+ 2.6939P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max< 0.001

Δρ_max= 0.69 e Å⁻³

Δρ_min= −0.65 e Å⁻³

Acta Cryst. (2018). C74, 1171-1179

sup-1

supporting information

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full

covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and

torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.

An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

Occ. (<1)

O1

C1

H1A

H1B

C2

C3

C4

C5

0.6042 (2)

0.2119 (3)

0.2169

0.09574 (8)

0.02787 (10)

−0.0110

0.02605 (13)

0.00437 (17)

−0.0211

0.0343 (4)

0.0224 (5)

0.027*

0.1468

0.0265

0.0527

0.027*

0.3771 (3)

0.4690 (3)

0.3932 (3)

0.2261 (3)

0.1707

0.2296

0.4445 (3)

0.5488

0.04750 (9)

0.07967 (10)

0.09152 (10)

0.07064 (10)

0.0971

0.0329

0.04187 (10)

0.0566

0.05106 (16)

−0.00795 (17)

−0.11067 (17)

−0.14871 (17)

−0.1986

−0.1785

0.14446 (17)

0.1639

0.0210 (5)

0.0230 (5)

0.0218 (5)

0.0227 (5)

0.027*

0.0226 (5)

0.027*

H5A

H5B

C6

H6

C7

C8

H8

0.3796 (3)

0.4273 (3)

0.5014

0.01625 (10)

0.03902 (11)

0.0694

0.22028 (17)

0.31209 (18)

0.3232

0.0229 (5)

0.0278 (5)

0.033*

C9

H9

0.3683 (3)

0.3993

0.01808 (11)

0.0348

0.38682 (18)

0.4483

0.0287 (5)

0.034*

C10

C11

H11

C12

H12

C13

C14

H14

C15

C16

H16

C17

H17

C18

C19

H19

C20

H20

C21

C22

C23

H23

0.2636 (3)

0.2186 (3)

0.1489

0.2746 (3)

0.2418

0.2037 (3)

0.4793 (3)

0.5802

0.4379 (3)

0.5050 (3)

0.5766

0.4692 (4)

0.5156

0.3644 (3)

0.3013 (3)

0.2331

0.3378 (3)

0.2943

0.3248 (4)

0.1810 (3)

0.2330 (3)

0.1926

−0.02744 (10)

−0.05167 (10)

−0.0834

−0.02990 (10)

−0.0463

−0.05211 (11)

0.12141 (10)

0.1337

0.13748 (10)

0.18706 (12)

0.2086

0.20519 (12)

0.2389

0.17365 (11)

0.12340 (10)

0.1013

0.10541 (10)

0.0708

0.19397 (14)

0.17179 (9)

0.16704 (10)

0.1380

0.37199 (18)

0.28188 (17)

0.2720

0.20634 (17)

0.1448

0.45243 (19)

−0.16082 (17)

−0.1262

−0.26189 (17)

−0.28977 (19)

−0.2434

−0.3833 (2)

−0.4010

−0.45169 (18)

−0.42675 (18)

−0.4740

−0.33248 (17)

−0.3157

−0.5530 (2)

0.01432 (16)

0.11316 (17)

0.1470

0.0260 (5)

0.0253 (5)

0.030*

0.0234 (5)

0.028*

0.0332 (6)

0.0238 (5)

0.029*

0.0254 (5)

0.0351 (6)

0.042*

0.0391 (7)

0.047*

0.0308 (6)

0.0278 (5)

0.033*

0.0253 (5)

0.030*

0.0449 (7)

0.0209 (5)

0.0228 (5)

0.027*

Acta Cryst. (2018). C74, 1171-1179

sup-2

supporting information

C24

H24

C25

C26

H26

C27

H27

C28

H28A

H28B

H28C

C29

H29A

H29B

Cl1

Cl2

F1

F2

F3

F4

F5

F6

F4′

F5′

F6′

0.3443 (3)

0.3798

0.4053 (3)

0.3515 (3)

0.3920

0.2402 (3)

0.2049

0.5273 (4)

0.5058

0.5227

0.6328

0.8703 (3)

0.8038

0.9529

0.96073 (11)

0.75207 (10)

0.2185 (2)

0.0510 (2)

0.2815 (3)

0.193 (3)

0.4359 (17)

0.3157 (16)

0.255 (4)

0.226 (3)

0.4461 (11)

0.1363 (2)

−0.0492 (2)

−0.0339 (2)

0.04238 (7)

0.20520 (10)

0.2022

0.24791 (10)

0.25165 (10)

0.2807

0.21396 (10)

0.2169

0.28894 (13)

0.2972

0.3243

0.2721

0.13523 (12)

0.1310

0.1639

0.06994 (3)

0.15934 (4)

−0.01731 (8)

−0.06637 (10)

−0.09948 (8)

0.1743 (11)

0.1789 (8)

0.2480 (4)

0.2452 (7)

0.1614 (10)

0.1994 (9)

0.06618 (8)

0.10275 (8)

0.14734 (7)

0.12239 (2)

0.16107 (17)

0.2283

0.11270 (19)

0.01411 (19)

−0.0197

−0.03562 (17)

−0.1029

0.1653 (2)

0.2280

0.1287

0.1736

0.2147 (2)

0.1495

0.2124

0.25227 (7)

0.29150 (6)

0.52703 (12)

0.42708 (13)

0.48702 (14)

−0.6004 (16)

−0.5972 (8)

−0.5636 (7)

−0.5575 (10)

−0.6123 (15)

−0.5910 (7)

−0.07383 (13)

0.01773 (13)

−0.13659 (13)

−0.04711 (4)

0.0257 (5)

0.031*

0.0291 (6)

0.0312 (6)

0.037*

0.0263 (5)

0.032*

0.0435 (7)

0.065*

0.0350 (6)

0.042*

0.0580 (2)

0.0525 (2)

0.0533 (5)

0.0611 (6)

0.0662 (6)

0.106 (7)

0.107 (4)

0.064 (3)

0.127 (6)

0.087 (6)

0.114 (6)

0.0197 (4)

0.0325 (4)

0.0317 (4)

0.02246 (15)

0.51 (3)

0.49 (3)

N1

O2

O3

S1

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

O1

C1

C2

C3

C4

C5

C6

C7

C8

0.0214 (9)

0.0512 (12)

0.0220 (11)

0.0186 (11)

0.0255 (12)

0.0233 (11)

0.0267 (12)

0.0214 (11)

0.0234 (12)

0.0273 (12)

0.0314 (13)

0.0274 (12)

0.0236 (12)

0.0246 (12)

0.0363 (15)

0.0254 (12)

0.0287 (10)

0.0243 (12)

0.0233 (12)

0.0246 (13)

0.0223 (12)

0.0200 (12)

0.0264 (13)

0.0236 (13)

0.0272 (13)

0.0223 (13)

0.0259 (13)

0.0270 (13)

0.0214 (12)

0.0304 (14)

0.0247 (13)

−0.0091 (8)

−0.0020 (9)

0.0011 (9)

0.0025 (9)

0.0017 (9)

−0.0014 (9)

−0.0006 (9)

0.0020 (9)

−0.0062 (10)

−0.0063 (11)

0.0007 (10)

−0.0010 (10)

0.0024 (9)

0.0025 (8)

0.0021 (9)

0.0038 (9)

0.0061 (10)

0.0049 (9)

0.0053 (9)

0.0048 (10)

0.0032 (10)

0.0024 (10)

0.0056 (11)

0.0049 (10)

0.0027 (10)

0.0017 (9)

0.0083 (12)

0.0030 (10)

0.0042 (8)

0.0036 (9)

0.0196 (11)

0.0206 (11)

0.0195 (12)

0.0199 (11)

0.0218 (12)

0.0200 (11)

0.0208 (11)

0.0271 (13)

0.0323 (14)

0.0242 (12)

0.0237 (12)

0.0226 (12)

0.0334 (14)

0.0203 (11)

−0.0001 (9)

−0.0029 (9)

−0.0017 (9)

−0.0037 (9)

−0.0001 (9)

0.0031 (9)

−0.0008 (10)

−0.0041 (10)

0.0022 (10)

0.0007 (10)

−0.0003 (9)

−0.0015 (11)

−0.0016 (10)

C9

C10

C11

C12

C13

C14

−0.0065 (12)

0.0003 (9)

Acta Cryst. (2018). C74, 1171-1179

sup-3

supporting information

C15

C16

C17

C18

C19

C20

C21

C22

C23

C24

C25

C26

C27

C28

C29

Cl1

Cl2

F1

F2

F3

F4

F5

F6

F4′

F5′

F6′

0.0238 (12)

0.0389 (15)

0.0461 (17)

0.0353 (14)

0.0326 (13)

0.0287 (13)

0.054 (2)

0.0201 (11)

0.0252 (12)

0.0276 (13)

0.0314 (13)

0.0393 (15)

0.0336 (14)

0.0471 (18)

0.0333 (14)

0.0552 (5)

0.0503 (5)

0.0740 (13)

0.0443 (11)

0.0966 (16)

0.091 (7)

0.137 (10)

0.111 (6)

0.207 (15)

0.138 (17)

0.062 (5)

0.0176 (9)

0.0223 (9)

0.0296 (10)

0.0173 (3)

0.0291 (13)

0.0356 (14)

0.0375 (15)

0.0339 (14)

0.0267 (12)

0.0211 (11)

0.0446 (18)

0.0204 (11)

0.0220 (11)

0.0301 (13)

0.0257 (12)

0.0245 (12)

0.0240 (12)

0.0382 (16)

0.0382 (15)

0.0386 (4)

0.0603 (5)

0.0572 (11)

0.0990 (16)

0.0520 (11)

0.149 (16)

0.161 (8)

0.0247 (13)

0.0299 (14)

0.0332 (15)

0.0239 (13)

0.0253 (13)

0.0279 (13)

0.0345 (16)

0.0213 (12)

0.0220 (12)

0.0182 (12)

0.0291 (14)

0.0304 (14)

0.0196 (12)

0.0407 (17)

0.0343 (15)

0.0731 (6)

0.0525 (5)

0.0358 (10)

0.0428 (11)

0.0606 (13)

0.050 (9)

−0.0010 (10)

−0.0155 (12)

−0.0174 (13)

−0.0066 (11)

−0.0053 (11)

−0.0028 (10)

−0.0121 (15)

0.0020 (9)

0.0082 (10)

0.0056 (12)

0.0081 (13)

0.0085 (11)

0.0092 (11)

0.0101 (10)

0.0066 (15)

0.0031 (9)

0.0068 (10)

0.0027 (10)

0.0042 (11)

0.0089 (12)

0.0025 (10)

0.0006 (14)

0.0092 (12)

−0.0008 (4)

0.0233 (4)

0.0276 (9)

0.0158 (9)

0.0397 (12)

−0.043 (7)

0.054 (6)

0.0014 (10)

−0.0001 (11)

0.0055 (12)

0.0036 (11)

−0.0030 (10)

−0.0020 (10)

0.0090 (14)

−0.0038 (9)

0.0008 (9)

−0.0028 (10)

−0.0059 (10)

0.0011 (10)

0.0004 (9)

−0.0076 (13)

−0.0020 (12)

−0.0017 (4)

−0.0152 (4)

−0.0126 (8)

−0.0047 (10)

0.0311 (10)

0.053 (8)

0.035 (4)

0.016 (2)

0.053 (6)

0.008 (3)

0.032 (6)

0.0006 (8)

−0.0092 (8)

−0.0020 (8)

−0.0038 (2)

0.0018 (9)

0.0032 (10)

−0.0028 (10)

−0.0080 (11)

−0.0018 (10)

−0.0171 (13)

0.0004 (12)

0.0080 (4)

−0.0012 (4)

−0.0242 (10)

−0.0341 (10)

0.0175 (11)

−0.078 (10)

0.075 (8)

−0.020 (4)

0.076 (9)

−0.065 (7)

−0.085 (9)

−0.0010 (7)

−0.0069 (8)

0.0046 (7)

0.040 (4)

0.037 (4)

0.070 (5)

0.030 (3)

0.034 (3)

0.112 (10)

0.077 (5)

0.245 (14)

0.0213 (10)

0.0379 (10)

0.0300 (9)

0.0243 (3)

−0.006 (4)

0.045 (8)

−0.018 (6)

−0.002 (4)

0.0028 (8)

0.0143 (8)

−0.0074 (8)

0.0017 (2)

0.030 (4)

N1

O2

O3

S1

0.0196 (10)

0.0407 (11)

0.0290 (10)

0.0244 (3)

0.0002 (2)

Geometric parameters (Å, º)

O1—C3

C1—N1

C1—C2

C1—H1A

C1—H1B

C2—C6

C2—C3

C3—C4

C4—C14

C4—C5

C5—N1

C5—H5A

C5—H5B

C6—C7

C6—H6

1.225 (3)

C17—C18

1.394 (4)

0.9500

1.383 (3)

1.499 (4)

1.388 (3)

0.9500

1.475 (3)

1.511 (3)

0.9900

C17—H17

C18—C19

C18—C21

C19—C20

C19—H19

C20—H20

C21—F6

0.9900

1.347 (3)

1.494 (3)

1.503 (3)

1.347 (3)

1.512 (3)

1.468 (3)

0.9900

1.465 (3)

0.9500

1.279 (10)

1.279 (19)

1.296 (10)

1.311 (18)

1.317 (9)

1.342 (16)

1.389 (3)

1.397 (3)

C21—F4

C21—F6′

C21—F5′

C21—F5

C21—F4′

C22—C27

C22—C23

Acta Cryst. (2018). C74, 1171-1179

sup-4

supporting information

C7—C8

C7—C12

C8—C9

C8—H8

C9—C10

C9—H9

C10—C11

C10—C13

C11—C12

C11—H11

C12—H12

C13—F1

C13—F2

C13—F3

C14—C15

C14—H14

C15—C20

C15—C16

C16—C17

C16—H16

1.399 (3)

1.401 (3)

1.381 (3)

0.9500

1.388 (3)

0.9500

1.390 (3)

1.489 (4)

1.385 (3)

0.9500

C22—S1

1.760 (2)

1.383 (3)

0.9500

1.392 (4)

0.9500

1.394 (4)

1.505 (4)

1.385 (3)

0.9500

0.9800

C23—C24

C23—H23

C24—C25

C24—H24

C25—C26

C25—C28

C26—C27

C26—H26

C27—H27

C28—H28A

C28—H28B

C28—H28C

C29—Cl1

C29—Cl2

C29—H29A

C29—H29B

N1—S1

0.9500

1.333 (3)

1.335 (3)

1.339 (3)

1.467 (3)

0.9500

1.399 (3)

1.401 (4)

1.380 (4)

0.9500

1.753 (3)

1.761 (3)

0.9900

1.6428 (19)

1.4309 (18)

1.4346 (18)

O2—S1

O3—S1

N1—C1—C2

N1—C1—H1A

C2—C1—H1A

N1—C1—H1B

C2—C1—H1B

H1A—C1—H1B

C6—C2—C3

C6—C2—C1

C3—C2—C1

O1—C3—C2

O1—C3—C4

C2—C3—C4

C14—C4—C3

C14—C4—C5

C3—C4—C5

N1—C5—C4

N1—C5—H5A

C4—C5—H5A

N1—C5—H5B

C4—C5—H5B

H5A—C5—H5B

C2—C6—C7

C2—C6—H6

C7—C6—H6

C8—C7—C12

C8—C7—C6

C12—C7—C6

111.56 (18)

109.3

C19—C18—C17

C19—C18—C21

C17—C18—C21

C18—C19—C20

C18—C19—H19

C20—C19—H19

C19—C20—C15

C19—C20—H20

C15—C20—H20

F6—C21—F4

120.3 (2)

120.5 (2)

119.2 (2)

119.8 (2)

120.1

120.9 (2)

119.5

108.0

116.7 (2)

124.7 (2)

118.4 (2)

120.9 (2)

120.3 (2)

118.8 (2)

116.8 (2)

125.2 (2)

117.9 (2)

112.36 (19)

109.1

107.9

129.1 (2)

115.4

118.4 (2)

117.7 (2)

123.9 (2)

119.5

105.8 (12)

104.9 (14)

104.0 (8)

107.9 (13)

106.8 (9)

105.7 (14)

115.3 (5)

112.7 (11)

114.3 (6)

114.9 (11)

110.6 (5)

109.6 (7)

120.8 (2)

120.07 (18)

119.13 (18)

119.1 (2)

120.5

F6′—C21—F5′

F6—C21—F5

F4—C21—F5

F6′—C21—F4′

F5′—C21—F4′

F6—C21—C18

F4—C21—C18

F6′—C21—C18

F5′—C21—C18

F5—C21—C18

F4′—C21—C18

C27—C22—C23

C27—C22—S1

C23—C22—S1

C24—C23—C22

C24—C23—H23

C22—C23—H23

120.5

Acta Cryst. (2018). C74, 1171-1179

sup-5

supporting information

C9—C8—C7

C9—C8—H8

C7—C8—H8

C8—C9—C10

C8—C9—H9

C10—C9—H9

C9—C10—C11

C9—C10—C13

C11—C10—C13

C12—C11—C10

C12—C11—H11

C10—C11—H11

C11—C12—C7

C11—C12—H12

C7—C12—H12

F1—C13—F2

121.1 (2)

119.4

119.9 (2)

120.0

119.8 (2)

120.7 (2)

119.5 (2)

120.4 (2)

119.8

120.3 (2)

119.8

C23—C24—C25

C23—C24—H24

C25—C24—H24

C24—C25—C26

C24—C25—C28

C26—C25—C28

C27—C26—C25

C27—C26—H26

C25—C26—H26

C26—C27—C22

C26—C27—H27

C22—C27—H27

C25—C28—H28A

C25—C28—H28B

H28A—C28—H28B

C25—C28—H28C

H28A—C28—H28C

H28B—C28—H28C

Cl1—C29—Cl2

Cl1—C29—H29A

Cl2—C29—H29A

Cl1—C29—H29B

Cl2—C29—H29B

H29A—C29—H29B

C5—N1—C1

121.3 (2)

119.4

118.5 (2)

120.9 (2)

120.6 (2)

121.4 (2)

119.3

119.0 (2)

120.5

109.5

111.82 (16)

109.3

119.8

106.5 (2)

105.2 (2)

106.2 (2)

113.6 (2)

112.5 (2)

112.3 (2)

128.6 (2)

115.7

F1—C13—F3

F2—C13—F3

F1—C13—C10

F2—C13—C10

F3—C13—C10

C4—C14—C15

C4—C14—H14

C15—C14—H14

C20—C15—C16

C20—C15—C14

C16—C15—C14

C17—C16—C15

C17—C16—H16

C15—C16—H16

C16—C17—C18

C16—C17—H17

C18—C17—H17

109.3

107.9

115.7

118.0 (2)

123.7 (2)

118.2 (2)

121.3 (2)

119.4

119.6 (2)

120.2

112.70 (18)

119.13 (15)

118.11 (15)

120.40 (11)

105.67 (10)

105.75 (10)

107.56 (11)

107.85 (11)

109.25 (10)

C5—N1—S1

C1—N1—S1

O2—S1—O3

O2—S1—N1

O3—S1—N1

O2—S1—C22

O3—S1—C22

N1—S1—C22

120.2

N1—C1—C2—C6

N1—C1—C2—C3

C6—C2—C3—O1

C1—C2—C3—O1

C6—C2—C3—C4

C1—C2—C3—C4

O1—C3—C4—C14

C2—C3—C4—C14

O1—C3—C4—C5

C2—C3—C4—C5

C14—C4—C5—N1

C3—C4—C5—N1

C3—C2—C6—C7

C1—C2—C6—C7

145.7 (2)

−29.1 (3)

5.9 (3)

−178.8 (2)

−174.8 (2)

0.5 (3)

−1.7 (3)

179.0 (2)

180.0 (2)

0.6 (3)

−150.9 (2)

27.2 (3)

175.6 (2)

0.7 (4)

C21—C18—C19—C20

C18—C19—C20—C15

C16—C15—C20—C19

C14—C15—C20—C19

C19—C18—C21—F6

C17—C18—C21—F6

C19—C18—C21—F4

C17—C18—C21—F4

C19—C18—C21—F6′

C17—C18—C21—F6′

C19—C18—C21—F5′

C17—C18—C21—F5′

C19—C18—C21—F5

C17—C18—C21—F5

−179.4 (3)

0.1 (4)

−2.5 (4)

179.0 (2)

145.8 (7)

−35.9 (8)

24.3 (17)

−157.5 (17)

−119.9 (11)

58.3 (11)

1.5 (14)

179.7 (14)

−96.6 (11)

81.7 (11)

Acta Cryst. (2018). C74, 1171-1179

sup-6

supporting information

C2—C6—C7—C8

−147.9 (3)

32.9 (4)

−2.4 (4)

178.4 (2)

2.0 (4)

−0.1 (4)

177.5 (2)

−1.5 (4)

−179.1 (2)

1.1 (4)

C19—C18—C21—F4′

120.2 (15)

−61.6 (15)

0.3 (3)

178.72 (18)

−0.2 (4)

0.1 (4)

−179.5 (2)

−0.1 (4)

179.5 (3)

0.3 (4)

−0.3 (4)

−178.74 (19)

−58.1 (2)

86.8 (2)

C2—C6—C7—C12

C12—C7—C8—C9

C6—C7—C8—C9

C17—C18—C21—F4′

C27—C22—C23—C24

S1—C22—C23—C24

C22—C23—C24—C25

C23—C24—C25—C26

C23—C24—C25—C28

C24—C25—C26—C27

C28—C25—C26—C27

C25—C26—C27—C22

C23—C22—C27—C26

S1—C22—C27—C26

C4—C5—N1—C1

C4—C5—N1—S1

C2—C1—N1—C5

C2—C1—N1—S1

C5—N1—S1—O2

C1—N1—S1—O2

C5—N1—S1—O3

C1—N1—S1—O3

C5—N1—S1—C22

C1—N1—S1—C22

C27—C22—S1—O2

C23—C22—S1—O2

C27—C22—S1—O3

C23—C22—S1—O3

C27—C22—S1—N1

C23—C22—S1—N1

C7—C8—C9—C10

C8—C9—C10—C11

C8—C9—C10—C13

C9—C10—C11—C12

C13—C10—C11—C12

C10—C11—C12—C7

C8—C7—C12—C11

C6—C7—C12—C11

C9—C10—C13—F1

C11—C10—C13—F1

C9—C10—C13—F2

C11—C10—C13—F2

C9—C10—C13—F3

C11—C10—C13—F3

C3—C4—C14—C15

C5—C4—C14—C15

C4—C14—C15—C20

C4—C14—C15—C16

C20—C15—C16—C17

C14—C15—C16—C17

C15—C16—C17—C18

C16—C17—C18—C19

C16—C17—C18—C21

C17—C18—C19—C20

0.8 (3)

−180.0 (2)

19.5 (4)

−162.9 (2)

140.7 (3)

−41.7 (3)

−99.6 (3)

78.0 (3)

177.9 (2)

−3.9 (4)

−29.5 (4)

152.1 (3)

2.5 (4)

−178.9 (3)

−0.1 (5)

−2.4 (4)

179.4 (3)

2.4 (4)

58.9 (2)

−86.3 (2)

172.46 (16)

−44.55 (18)

43.76 (19)

−173.25 (16)

−72.08 (18)

70.91 (18)

−153.82 (19)

27.7 (2)

−22.6 (2)

159.00 (18)

91.9 (2)

−86.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

C1—H1A···O1ⁱ

C1—H1A···O2ⁱⁱ

C5—H5B···Cl1ⁱ

C29—H29A···O1

C29—H29A···O2ⁱⁱⁱ

0.99

2.53

2.61

2.98

2.34

2.60

3.390 (3)

3.365 (3)

3.832 (2)

3.279 (3)

3.162 (3)

145

133

144

159

116

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) x+1, y, z.

(3E,5E)-1-(4-Fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one (5)

Crystal data

C₂₇H₁₈F₇NO₃S

M_r= 569.48

Triclinic, P1

a = 8.5664 (6) Å

b = 10.0932 (8) Å

c = 14.3871 (12) Å

α = 90.590 (4)°

β = 98.592 (4)°

γ = 97.309 (4)°

V = 1219.44 (17) Å³

Z = 2

F(000) = 580

D_x= 1.551 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Acta Cryst. (2018). C74, 1171-1179

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supporting information

Cell parameters from 4723 reflections

θ = 2.4–26.3°

µ = 0.22 mm⁻¹

T = 150 K

Block, yellow

0.26 × 0.17 × 0.10 mm

Data collection

Bruker SMART CCD area detector

diffractometer

3187 reflections with I > 2σ(I)

R_int= 0.074

Radiation source: sealed tube

phi and ω scans

21256 measured reflections

4790 independent reflections

θ_max= 26.0°, θ_min= 2.4°

h = −10→10

k = −12→12

l = −17→17

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.050

wR(F²) = 0.129

S = 1.01

4790 reflections

380 parameters

0 restraints

Hydrogen site location: inferred from

neighbouring sites

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0558P)²+ 0.8089P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max< 0.001

Δρ_max= 0.48 e Å⁻³

Δρ_min= −0.38 e Å⁻³

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full

covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and

torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.

An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

Occ. (<1)

C1

0.2745 (3)

0.2746

0.2856

0.4151 (3)

0.3998 (3)

0.2444 (3)

0.1130 (3)

0.1188

0.4646 (3)

0.4750

0.5549

0.3950 (3)

0.3125 (3)

0.2949 (3)

0.3682 (3)

0.4558

0.09345 (19)

0.1620

0.0671

0.07680 (18)

−0.01181 (18)

−0.07648 (18)

−0.05191 (18)

−0.0823

0.0266 (6)

0.032*

0.0229 (6)

0.0235 (6)

0.0233 (6)

0.0278 (6)

0.033*

H1A

H1B

C2

C3

C4

C5

H5A

H5B

C6

0.0089

0.5502 (3)

0.6278

0.3163

0.3970 (3)

0.3489

−0.0770

0.13772 (18)

0.1172

0.033*

0.0252 (6)

0.030*

H6

C7

C8

H8

0.5962 (3)

0.7029 (3)

0.7437

0.4619 (3)

0.4042 (3)

0.3262

0.23108 (18)

0.2959 (2)

0.2778

0.0231 (6)

0.0277 (6)

0.033*

C9

H9

0.7510 (3)

0.8232

0.4579 (3)

0.4168

0.3861 (2)

0.4296

0.0294 (6)

0.035*

C10

C11

H11

C12

0.6926 (3)

0.5903 (3)

0.5529

0.5725 (3)

0.6343 (3)

0.7141

0.41233 (19)

0.34794 (19)

0.3656

0.0260 (6)

0.0271 (6)

0.032*

0.5429 (3)

0.5799 (3)

0.25799 (19)

0.0249 (6)

Acta Cryst. (2018). C74, 1171-1179

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supporting information

H12

C13

C14

H14

C15

C16

H16

C17

H17

C18

C19

H19

C20

H20

C21

C22

C23

H23

C24

H24

C25

C26

H26

C27

H27

F1

F2

F3

F3′

F2′

F1′

F4

F5

F6

F7

N1

O1

O2

O3

S1

0.4735

0.6231

0.2140

0.030*

0.7432 (4)

0.2319 (3)

0.3198

0.1018 (3)

0.0801 (3)

0.1465

−0.0355 (3)

−0.0490

−0.1322 (3)

−0.1114 (4)

−0.1765

0.0040 (3)

0.0173

−0.2521 (4)

0.1738 (3)

0.2648 (3)

0.2506

0.3765 (3)

0.4408

0.3913 (3)

0.3034 (3)

0.3173

0.6305 (3)

0.2154 (3)

0.1678

0.1914 (3)

0.0706 (3)

0.0043

0.0453 (3)

−0.0380

0.1420 (3)

0.2635 (3)

0.3303

0.2877 (3)

0.3714

0.1177 (4)

0.1683 (3)

0.1949 (3)

0.2695

0.1122 (3)

0.1290

0.0050 (3)

−0.0243 (3)

−0.1000

0.5094 (2)

−0.15292 (19)

−0.1564

−0.23187 (18)

−0.2831 (2)

−0.2639

−0.3610 (2)

−0.3945

−0.3901 (2)

−0.3416 (2)

−0.3621

−0.26338 (19)

−0.2303

−0.4773 (2)

0.15526 (18)

0.24334 (19)

0.2805

0.2766 (2)

0.3363

0.2207 (2)

0.1338 (2)

0.0976

0.0331 (7)

0.0252 (6)

0.030*

0.0254 (6)

0.0328 (7)

0.039*

0.0361 (7)

0.043*

0.0316 (7)

0.0349 (7)

0.042*

0.0298 (6)

0.036*

0.0420 (8)

0.0225 (6)

0.0277 (6)

0.033*

0.0318 (7)

0.038*

0.0324 (7)

0.0332 (7)

0.040*

0.1933 (3)

0.1315

0.0600 (3)

0.0436

0.1001 (2)

0.0396

0.0283 (6)

0.034*

0.6329 (10)

0.763 (2)

0.8690 (9)

0.8703 (14)

0.6354 (14)

0.783 (3)

−0.3734 (2)

−0.3093 (3)

−0.1910 (2)

0.4980 (2)

0.1225 (2)

0.5140 (2)

0.0046 (2)

−0.0936 (2)

0.03566 (8)

0.6923 (9)

0.5383 (5)

0.7143 (13)

0.5860 (14)

0.613 (2)

0.7594 (7)

0.1880 (3)

−0.0095 (2)

0.1550 (2)

−0.0776 (2)

0.3894 (2)

0.26338 (19)

0.3482 (2)

0.2044 (2)

0.27738 (7)

0.5414 (5)

0.5743 (3)

0.5196 (5)

0.5537 (7)

0.5590 (7)

0.5101 (6)

−0.47810 (15)

−0.49351 (16)

−0.55509 (12)

0.25495 (13)

0.04994 (15)

−0.03256 (13)

0.19369 (14)

0.05130 (15)

0.11325 (5)

0.061 (3)

0.077 (4)

0.076 (4)

0.079 (5)

0.119 (8)

0.096 (6)

0.0800 (8)

0.0797 (8)

0.0499 (5)

0.0534 (5)

0.0243 (5)

0.0310 (5)

0.0369 (5)

0.0384 (5)

0.02732 (19)

0.542 (19)

0.458 (19)

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

C1

C2

C3

C4

0.0285 (14)

0.0271 (14)

0.0266 (14)

0.0254 (14)

0.0253 (15)

0.0199 (14)

0.0219 (14)

0.0235 (14)

0.0277 (15)

0.0241 (14)

0.0242 (14)

0.0236 (14)

0.0074 (12)

0.0063 (11)

0.0067 (11)

0.0083 (11)

0.0068 (12)

0.0093 (11)

0.0075 (11)

0.0081 (11)

−0.0020 (12)

0.0023 (11)

0.0031 (11)

0.0038 (11)

Acta Cryst. (2018). C74, 1171-1179

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supporting information

C5

C6

C7

C8

0.0301 (15)

0.0267 (14)

0.0229 (13)

0.0280 (14)

0.0286 (15)

0.0256 (14)

0.0310 (15)

0.0271 (14)

0.0379 (17)

0.0229 (13)

0.0251 (14)

0.0265 (14)

0.0311 (16)

0.0250 (14)

0.0368 (17)

0.0361 (16)

0.0342 (17)

0.0219 (13)

0.0332 (15)

0.0353 (16)

0.0302 (15)

0.0397 (17)

0.0298 (15)

0.065 (5)

0.0319 (16)

0.0237 (15)

0.0238 (14)

0.0242 (15)

0.0306 (16)

0.0265 (15)

0.0236 (15)

0.0223 (14)

0.0293 (17)

0.0248 (15)

0.0283 (15)

0.0358 (17)

0.0358 (18)

0.0378 (18)

0.0368 (18)

0.0278 (15)

0.049 (2)

0.0216 (14)

0.0277 (15)

0.0363 (17)

0.0339 (17)

0.0276 (16)

0.0265 (15)

0.091 (6)

0.0235 (14)

0.0281 (15)

0.0240 (14)

0.0329 (16)

0.0289 (16)

0.0256 (15)

0.0280 (15)

0.0251 (15)

0.0307 (16)

0.0296 (15)

0.0238 (14)

0.0362 (17)

0.0403 (18)

0.0307 (16)

0.0317 (17)

0.0257 (15)

0.0399 (19)

0.0252 (14)

0.0234 (15)

0.0243 (15)

0.0368 (17)

0.0351 (17)

0.0287 (15)

0.031 (3)

0.0126 (12)

0.0076 (11)

0.0034 (11)

0.0068 (12)

0.0066 (12)

0.0006 (12)

0.0062 (12)

0.0042 (11)

0.0036 (14)

0.0049 (11)

0.0006 (12)

0.0043 (13)

−0.0006 (13)

−0.0044 (13)

0.0074 (14)

0.0034 (13)

−0.0007 (15)

0.0042 (11)

0.0067 (12)

0.0083 (13)

0.0148 (13)

0.0115 (13)

0.0048 (12)

0.043 (5)

0.0038 (12)

0.0101 (12)

0.0075 (11)

0.0081 (12)

0.0016 (12)

0.0056 (12)

0.0066 (12)

0.0028 (11)

0.0008 (14)

0.0080 (11)

0.0091 (11)

0.0056 (13)

0.0065 (14)

0.0068 (12)

0.0049 (14)

0.0062 (13)

0.0025 (15)

0.0063 (11)

0.0059 (12)

0.0024 (12)

0.0078 (13)

0.0091 (14)

0.0042 (12)

−0.002 (3)

−0.011 (4)

0.019 (3)

−0.0006 (12)

0.0014 (11)

0.0031 (11)

0.0005 (12)

0.0035 (12)

0.0027 (12)

0.0002 (12)

0.0021 (11)

−0.0011 (13)

0.0011 (12)

0.0004 (12)

−0.0052 (14)

−0.0104 (14)

0.0026 (13)

0.0088 (14)

0.0016 (12)

−0.0023 (16)

0.0030 (11)

0.0005 (12)

0.0058 (13)

0.0082 (13)

−0.0018 (13)

−0.0023 (12)

−0.022 (3)

0.0051 (18)

−0.036 (5)

−0.033 (5)

−0.045 (9)

−0.008 (3)

−0.0291 (15)

0.0098 (12)

0.0023 (9)

0.0096 (10)

−0.0005 (10)

−0.0062 (9)

0.0030 (10)

0.0019 (10)

0.0017 (3)

C9

C10

C11

C12

C13

C14

C15

C16

C17

C18

C19

C20

C21

C22

C23

C24

C25

C26

C27

F1

F2

F3

F3′

F2′

F1′

F4

F5

F6

F7

N1

0.162 (12)

0.061 (4)

0.081 (6)

0.037 (3)

0.104 (10)

0.095 (9)

0.23 (2)

0.032 (3)

0.026 (2)

0.052 (4)

0.055 (5)

0.041 (5)

0.024 (4)

−0.047 (4)

0.055 (6)

−0.044 (4)

0.033 (5)

0.069 (8)

−0.071 (10)

−0.012 (5)

0.0360 (13)

−0.0307 (13)

0.0093 (10)

0.0399 (10)

0.0085 (10)

0.0138 (9)

0.186 (16)

0.0400 (12)

0.0899 (17)

0.0537 (12)

0.0586 (12)

0.0237 (11)

0.0285 (10)

0.0414 (12)

0.0212 (10)

0.0225 (3)

0.050 (4)

−0.029 (7)

−0.0095 (10)

−0.0355 (13)

0.0014 (9)

0.0041 (9)

0.0061 (9)

0.0060 (8)

0.0206 (9)

−0.0021 (9)

0.0079 (3)

0.141 (2)

0.0594 (14)

0.0673 (15)

0.0344 (11)

0.0484 (12)

0.0245 (12)

0.0319 (11)

0.0338 (12)

0.0455 (13)

0.0300 (4)

0.0570 (15)

0.0604 (13)

0.0606 (13)

0.0269 (13)

0.0352 (11)

0.0437 (13)

0.0460 (13)

0.0323 (4)

O1

O2

O3

S1

0.0190 (10)

0.0031 (9)

0.0100 (3)

Geometric parameters (Å, º)

C1—N1

C1—C2

C1—H1A

C1—H1B

C2—C6

C2—C3

C3—O1

1.469 (3)

1.516 (3)

0.9900

C14—C15

1.462 (4)

0.9500

1.396 (4)

1.398 (4)

1.378 (4)

0.9500

C14—H14

C15—C16

C15—C20

C16—C17

C16—H16

C17—C18

0.9900

1.341 (4)

1.495 (4)

1.225 (3)

1.388 (4)

Acta Cryst. (2018). C74, 1171-1179

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supporting information

C3—C4

C4—C14

C4—C5

1.495 (4)

1.338 (4)

1.505 (3)

1.467 (3)

0.9900

1.465 (4)

0.9500

1.391 (4)

1.400 (4)

1.384 (4)

0.9500

1.387 (4)

0.9500

1.387 (4)

1.489 (4)

1.383 (4)

0.9500

C17—H17

C18—C19

C18—C21

C19—C20

C19—H19

C20—H20

C21—F5

C21—F4

C21—F6

C22—C27

C22—C23

C22—S1

C23—C24

C23—H23

C24—C25

C24—H24

C25—F7

C25—C26

C26—C27

C26—H26

C27—H27

N1—S1

0.9500

1.383 (4)

1.494 (4)

1.380 (4)

0.9500

C5—N1

C5—H5A

C5—H5B

C6—C7

C6—H6

C7—C8

C7—C12

C8—C9

C8—H8

C9—C10

C9—H9

C10—C11

C10—C13

C11—C12

C11—H11

C12—H12

C13—F2′

C13—F3

C13—F1′

C13—F3′

C13—F1

C13—F2

0.9500

1.320 (4)

1.330 (4)

1.343 (4)

1.386 (4)

1.390 (4)

1.763 (2)

1.384 (4)

0.9500

1.372 (4)

0.9500

1.357 (3)

1.368 (4)

1.387 (4)

0.9500

1.246 (9)

1.272 (7)

1.303 (8)

1.310 (6)

1.331 (7)

1.333 (5)

0.9500

1.634 (2)

1.430 (2)

1.431 (2)

O2—S1

O3—S1

N1—C1—C2

N1—C1—H1A

C2—C1—H1A

N1—C1—H1B

C2—C1—H1B

H1A—C1—H1B

C6—C2—C3

C6—C2—C1

C3—C2—C1

O1—C3—C4

O1—C3—C2

C4—C3—C2

C14—C4—C3

C14—C4—C5

C3—C4—C5

N1—C5—C4

N1—C5—H5A

C4—C5—H5A

N1—C5—H5B

C4—C5—H5B

H5A—C5—H5B

C2—C6—C7

111.8 (2)

109.3

C4—C14—C15

C4—C14—H14

C15—C14—H14

C16—C15—C20

C16—C15—C14

C20—C15—C14

C17—C16—C15

C17—C16—H16

C15—C16—H16

C16—C17—C18

C16—C17—H17

C18—C17—H17

C19—C18—C17

C19—C18—C21

C17—C18—C21

C20—C19—C18

C20—C19—H19

C18—C19—H19

C19—C20—C15

C19—C20—H20

C15—C20—H20

F5—C21—F4

129.0 (2)

115.5

117.6 (3)

119.0 (2)

123.2 (3)

121.5 (3)

119.2

107.9

117.2 (2)

124.8 (2)

117.9 (2)

120.4 (2)

120.6 (2)

119.0 (2)

117.6 (2)

124.3 (2)

118.1 (2)

112.3 (2)

109.1

119.2

119.6 (3)

120.2

120.0 (3)

120.1 (3)

119.8 (3)

119.9 (3)

120.0

121.2 (3)

119.4

109.1

107.9

119.4

108.6 (3)

129.8 (2)

Acta Cryst. (2018). C74, 1171-1179

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supporting information

C2—C6—H6

C7—C6—H6

C8—C7—C12

C8—C7—C6

C12—C7—C6

C9—C8—C7

C9—C8—H8

C7—C8—H8

C8—C9—C10

C8—C9—H9

C10—C9—H9

C11—C10—C9

C11—C10—C13

C9—C10—C13

C12—C11—C10

C12—C11—H11

C10—C11—H11

C11—C12—C7

C11—C12—H12

C7—C12—H12

F2′—C13—F1′

F2′—C13—F3′

F1′—C13—F3′

F3—C13—F1

F3—C13—F2

F1—C13—F2

F2′—C13—C10

F3—C13—C10

F1′—C13—C10

F3′—C13—C10

F1—C13—C10

F2—C13—C10

115.1

F5—C21—F6

F4—C21—F6

104.6 (3)

103.8 (3)

113.4 (3)

113.2 (3)

112.5 (3)

120.9 (2)

120.3 (2)

118.8 (2)

119.7 (3)

120.2

118.2 (2)

117.7 (2)

124.1 (2)

121.5 (2)

119.3

119.3 (2)

120.3

F5—C21—C18

F4—C21—C18

F6—C21—C18

C27—C22—C23

C27—C22—S1

C23—C22—S1

C24—C23—C22

C24—C23—H23

C22—C23—H23

C25—C24—C23

C25—C24—H24

C23—C24—H24

F7—C25—C26

F7—C25—C24

C26—C25—C24

C25—C26—C27

C25—C26—H26

C27—C26—H26

C22—C27—C26

C22—C27—H27

C26—C27—H27

C5—N1—C1

120.3

120.2

117.9 (3)

121.0

120.2 (3)

120.2 (2)

119.6 (2)

120.1 (2)

120.0

120.6 (2)

119.7

121.0

118.6 (3)

117.5 (3)

123.9 (3)

117.9 (3)

121.0

119.6 (3)

120.2

119.7

105.2 (8)

108.7 (7)

103.8 (6)

105.9 (5)

107.9 (5)

100.2 (5)

112.7 (5)

114.8 (4)

112.3 (4)

113.5 (4)

113.3 (3)

120.2

112.9 (2)

120.87 (19)

117.40 (18)

119.80 (12)

106.01 (12)

106.49 (12)

106.57 (12)

109.23 (13)

108.28 (11)

C5—N1—S1

C1—N1—S1

O2—S1—O3

O2—S1—N1

O3—S1—N1

O2—S1—C22

O3—S1—C22

N1—S1—C22

N1—C1—C2—C6

N1—C1—C2—C3

C6—C2—C3—O1

C1—C2—C3—O1

C6—C2—C3—C4

C1—C2—C3—C4

O1—C3—C4—C14

C2—C3—C4—C14

O1—C3—C4—C5

C2—C3—C4—C5

C14—C4—C5—N1

C3—C4—C5—N1

C3—C2—C6—C7

C1—C2—C6—C7

C2—C6—C7—C8

−146.5 (3)

30.3 (3)

C20—C15—C16—C17

C14—C15—C16—C17

C15—C16—C17—C18

C16—C17—C18—C19

C16—C17—C18—C21

C17—C18—C19—C20

C21—C18—C19—C20

C18—C19—C20—C15

C16—C15—C20—C19

C14—C15—C20—C19

C19—C18—C21—F5

C17—C18—C21—F5

C19—C18—C21—F4

C17—C18—C21—F4

C19—C18—C21—F6

−1.3 (4)

−176.7 (3)

0.6 (5)

−9.1 (4)

173.9 (2)

173.1 (2)

−4.0 (4)

5.3 (4)

−176.9 (2)

−174.3 (2)

3.5 (4)

150.8 (3)

−29.6 (3)

−176.6 (3)

0.2 (5)

0.5 (4)

176.9 (3)

−0.9 (4)

−177.3 (3)

0.2 (4)

0.9 (4)

176.2 (3)

−152.5 (3)

31.1 (4)

−28.2 (4)

155.4 (3)

89.0 (3)

151.6 (3)

Acta Cryst. (2018). C74, 1171-1179

sup-12

supporting information

C2—C6—C7—C12

C12—C7—C8—C9

C6—C7—C8—C9

−30.2 (5)

2.6 (4)

−179.1 (3)

−0.5 (4)

−1.7 (4)

179.7 (3)

1.7 (4)

−179.7 (3)

0.4 (4)

−2.6 (4)

179.2 (3)

73.8 (14)

−107.6 (13)

−89.8 (8)

88.7 (8)

−44.8 (11)

133.8 (11)

−162.1 (10)

16.4 (10)

32.2 (6)

−149.2 (6)

145.6 (8)

−35.8 (9)

−173.1 (3)

6.5 (5)

C17—C18—C21—F6

−87.4 (4)

0.0 (4)

−178.5 (2)

−0.7 (4)

−178.3 (3)

0.5 (5)

179.2 (3)

0.4 (5)

1.0 (4)

179.5 (2)

−1.1 (4)

58.2 (3)

−88.3 (3)

−58.4 (3)

89.4 (2)

−154.37 (18)

60.6 (2)

−25.8 (2)

−170.82 (17)

91.6 (2)

−53.5 (2)

161.2 (2)

−20.3 (3)

30.5 (3)

C27—C22—C23—C24

S1—C22—C23—C24

C22—C23—C24—C25

C23—C24—C25—F7

C23—C24—C25—C26

F7—C25—C26—C27

C24—C25—C26—C27

C23—C22—C27—C26

S1—C22—C27—C26

C25—C26—C27—C22

C4—C5—N1—C1

C4—C5—N1—S1

C2—C1—N1—C5

C2—C1—N1—S1

C5—N1—S1—O2

C1—N1—S1—O2

C5—N1—S1—O3

C1—N1—S1—O3

C5—N1—S1—C22

C1—N1—S1—C22

C27—C22—S1—O2

C23—C22—S1—O2

C27—C22—S1—O3

C23—C22—S1—O3

C27—C22—S1—N1

C23—C22—S1—N1

C7—C8—C9—C10

C8—C9—C10—C11

C8—C9—C10—C13

C9—C10—C11—C12

C13—C10—C11—C12

C10—C11—C12—C7

C8—C7—C12—C11

C6—C7—C12—C11

C11—C10—C13—F2′

C9—C10—C13—F2′

C11—C10—C13—F3

C9—C10—C13—F3

C11—C10—C13—F1′

C9—C10—C13—F1′

C11—C10—C13—F3′

C9—C10—C13—F3′

C11—C10—C13—F1

C9—C10—C13—F1

C11—C10—C13—F2

C9—C10—C13—F2

C3—C4—C14—C15

C5—C4—C14—C15

C4—C14—C15—C16

C4—C14—C15—C20

−151.0 (2)

−85.1 (2)

93.4 (2)

−154.1 (3)

30.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

C26—H26···O1ⁱ

C23—H23···F2′ⁱⁱ

C23—H23···F1ⁱⁱ

C1—H1B···O1ⁱⁱⁱ

0.95

0.99

2.58

2.61

2.46

3.458 (3)

3.364 (12)

3.242 (7)

3.293 (3)

154

140

124

142

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z.

(3E,5E)-1-(4-Nitrobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one (6)

Crystal data

C₂₇H₁₈F₆N₂O₅S

M_r= 596.49

Triclinic, P1

γ = 98.971 (5)°

V = 1245.7 (2) Å³

Z = 2

a = 7.4346 (7) Å

b = 11.6714 (11) Å

c = 14.6479 (15) Å

α = 90.825 (5)°

β = 96.884 (5)°

F(000) = 608

D_x= 1.590 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 5944 reflections

θ = 2.3–26.4°

Acta Cryst. (2018). C74, 1171-1179

sup-13

supporting information

µ = 0.22 mm⁻¹

T = 150 K

Block, yellow

0.18 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD area detector

diffractometer

3350 reflections with I > 2σ(I)

R_int= 0.072

Radiation source: sealed tube

phi and ω scans

θ_max= 26.0°, θ_min= 2.2°

h = −9→9

23092 measured reflections

4848 independent reflections

k = −14→14

l = −18→18

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.051

wR(F²) = 0.129

S = 1.03

4848 reflections

370 parameters

0 restraints

Hydrogen site location: inferred from

neighbouring sites

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0531P)²+ 1.0046P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max< 0.001

Δρ_max= 0.41 e Å⁻³

Δρ_min= −0.41 e Å⁻³

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full

covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and

torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.

An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

C1

0.2697 (3)

0.3550

0.3403

0.1802 (3)

−0.0101 (3)

−0.0992 (4)

0.0042 (4)

0.0792

0.2808 (2)

0.3436

0.2411

0.1958 (2)

0.1329 (2)

0.1547 (2)

0.2409 (2)

0.2012

0.99958 (18)

1.0356

0.9594

1.06333 (18)

1.03293 (18)

0.93983 (18)

0.88225 (18)

0.8444

0.0237 (6)

0.028*

0.0218 (6)

0.0228 (6)

0.0233 (6)

0.0244 (6)

0.029*

H1A

H1B

C2

C3

C4

C5

H5A

H5B

C6

−0.0830

0.2579 (4)

0.1800

0.2778

0.1728 (2)

0.1231

0.8404

1.14696 (18)

1.1815

0.029*

0.0241 (6)

0.029*

H6

C7

C8

H8

0.4435 (3)

0.4688 (4)

0.3655

0.2119 (2)

0.2154 (3)

0.1964

1.19402 (18)

1.29007 (19)

1.3225

0.0226 (6)

0.0310 (7)

0.037*

C9

H9

0.6414 (4)

0.6561

0.2460 (3)

0.2499

1.3389 (2)

1.4043

0.0319 (7)

0.038*

C10

C11

H11

C12

H12

0.7924 (4)

0.7714 (4)

0.8758

0.5980 (4)

0.5839

0.2710 (2)

0.2664 (2)

0.2830

0.2377 (2)

0.2354

1.29146 (19)

1.19627 (19)

1.1643

1.14770 (19)

1.0823

0.0266 (6)

0.0244 (6)

0.029*

0.0242 (6)

0.029*

Acta Cryst. (2018). C74, 1171-1179

sup-14

supporting information

C13

C14

H14

C15

C16

H16

C17

H17

C18

C19

H19

C20

H20

C21

C22

C23

H23

C24

H24

C25

C26

H26

C27

H27

F1

F2

F3

F4

F5

F6

N1

N2

O1

O2

O3

O4

O5

0.9797 (4)

−0.2679 (4)

−0.3218

−0.3797 (4)

−0.5702 (4)

−0.6225

−0.6826 (4)

−0.8116

−0.6080 (4)

−0.4201 (4)

−0.3687

−0.3071 (4)

−0.1780

−0.7317 (5)

0.2910 (3)

0.4795 (4)

0.5426

0.5737 (4)

0.7028

0.4765 (4)

0.2900 (4)

0.2278

0.2955 (3)

0.0956 (2)

0.0480

0.0941 (2)

0.0620 (2)

0.0434

0.0571 (2)

0.0367

0.0817 (3)

0.1100 (3)

0.1257

0.1154 (2)

0.1339

0.0732 (3)

0.4401 (2)

0.4413 (2)

0.4528

0.4254 (2)

0.4268

0.4076 (2)

0.4064 (2)

0.3947

1.3438 (2)

0.91185 (19)

0.9566

0.82299 (19)

0.8190 (2)

0.8741

0.7373 (2)

0.7362

0.6561 (2)

0.6575 (2)

0.6018

0.7399 (2)

0.7402

0.5674 (3)

0.80587 (18)

0.82156 (19)

0.8821

0.7475 (2)

0.7562

0.6611 (2)

0.6445 (2)

0.5838

0.0385 (8)

0.0248 (6)

0.030*

0.0249 (6)

0.0281 (6)

0.034*

0.0347 (7)

0.042*

0.0368 (7)

0.0360 (7)

0.043*

0.0298 (6)

0.036*

0.0512 (9)

0.0225 (6)

0.0268 (6)

0.032*

0.0317 (7)

0.038*

0.0299 (7)

0.0323 (7)

0.039*

0.1952 (4)

0.0663

0.4224 (2)

0.4214

0.71799 (19)

0.7086

0.0287 (6)

0.034*

1.1028 (2)

1.0477 (2)

0.9829 (3)

−0.6494 (4)

−0.8768 (4)

−0.7900 (3)

0.1234 (3)

0.5775 (4)

−0.0883 (2)

0.2915 (2)

−0.0020 (2)

0.7417 (3)

0.4897 (4)

0.16976 (9)

0.35879 (16)

0.19669 (19)

0.3491 (3)

0.1212 (3)

0.1228 (3)

−0.03590 (19)

0.32961 (18)

0.3884 (2)

0.06280 (16)

0.52922 (15)

0.48987 (16)

0.3840 (2)

0.3747 (2)

0.45813 (6)

1.29868 (14)

1.36152 (16)

1.42395 (16)

0.49823 (18)

0.5723 (2)

0.53857 (15)

0.94353 (15)

0.5824 (2)

1.08281 (13)

0.96959 (12)

0.86577 (13)

0.59848 (18)

0.50595 (18)

0.90097 (5)

0.0502 (5)

0.0626 (7)

0.0943 (10)

0.1085 (12)

0.1092 (11)

0.0697 (7)

0.0233 (5)

0.0431 (7)

0.0290 (5)

0.0265 (4)

0.0277 (4)

0.0606 (7)

0.0665 (8)

0.02288 (18)

S1

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

C1

C2

C3

C4

C5

C6

0.0206 (13)

0.0223 (13)

0.0226 (14)

0.0231 (14)

0.0227 (14)

0.0226 (14)

0.0262 (14)

0.0209 (13)

0.0251 (14)

0.0232 (14)

0.0261 (14)

0.0263 (14)

0.0226 (14)

0.0217 (14)

0.0213 (14)

0.0223 (14)

0.0209 (14)

0.0241 (15)

0.0013 (11)

0.0014 (10)

0.0033 (11)

0.0019 (11)

−0.0019 (11)

0.0032 (11)

−0.0016 (11)

0.0033 (11)

0.0058 (11)

0.0000 (11)

−0.0037 (11)

0.0060 (12)

0.0016 (11)

0.0011 (11)

−0.0011 (11)

−0.0008 (11)

−0.0004 (11)

0.0022 (11)

Acta Cryst. (2018). C74, 1171-1179

sup-15

supporting information

C7

C8

C9

0.0207 (13)

0.0251 (15)

0.0290 (15)

0.0250 (14)

0.0215 (14)

0.0270 (14)

0.0276 (16)

0.0260 (14)

0.0212 (14)

0.0238 (14)

0.0231 (15)

0.0375 (17)

0.0390 (17)

0.0234 (14)

0.049 (2)

0.0234 (14)

0.0269 (15)

0.0271 (15)

0.0362 (16)

0.0381 (17)

0.0246 (14)

0.0271 (10)

0.0273 (10)

0.0377 (12)

0.095 (2)

0.0231 (13)

0.0452 (17)

0.0486 (18)

0.0279 (15)

0.0253 (14)

0.0235 (14)

0.056 (2)

0.0225 (14)

0.0195 (13)

0.0237 (14)

0.0285 (16)

0.0289 (16)

0.0338 (16)

0.0318 (15)

0.044 (2)

0.0209 (13)

0.0294 (15)

0.0328 (16)

0.0265 (15)

0.0363 (16)

0.0341 (16)

0.0541 (12)

0.0755 (15)

0.185 (3)

0.0241 (14)

0.0244 (16)

0.0200 (15)

0.0275 (15)

0.0273 (15)

0.0226 (14)

0.0327 (18)

0.0255 (15)

0.0309 (16)

0.0354 (17)

0.048 (2)

0.0049 (11)

0.0095 (13)

0.0157 (13)

0.0096 (11)

0.0054 (11)

0.0046 (11)

0.0130 (15)

0.0025 (11)

−0.0018 (11)

0.0001 (11)

0.0009 (12)

0.0003 (13)

−0.0060 (13)

−0.0035 (12)

−0.0060 (17)

0.0018 (11)

0.0007 (11)

0.0060 (12)

0.0049 (12)

0.0044 (13)

0.0053 (12)

−0.0043 (8)

0.0151 (10)

0.0176 (15)

−0.0474 (18)

0.0623 (19)

−0.0123 (12)

−0.0013 (9)

0.0057 (13)

−0.0026 (8)

−0.0017 (8)

0.0072 (8)

0.0005 (11)

0.0035 (12)

−0.0015 (12)

−0.0016 (12)

0.0041 (12)

0.0043 (12)

−0.0020 (14)

0.0035 (12)

−0.0027 (12)

0.0025 (13)

−0.0087 (14)

−0.0162 (14)

−0.0039 (14)

−0.0007 (12)

−0.0198 (18)

0.0016 (11)

0.0017 (12)

0.0069 (13)

0.0124 (13)

0.0014 (13)

0.0001 (12)

−0.0087 (9)

−0.0017 (10)

−0.0155 (11)

−0.0445 (15)

−0.0620 (17)

−0.0309 (12)

−0.0014 (10)

0.0235 (15)

0.0056 (9)

0.0050 (11)

0.0077 (13)

0.0022 (13)

0.0009 (12)

0.0012 (11)

0.0010 (11)

0.0042 (15)

−0.0008 (11)

−0.0011 (11)

0.0005 (12)

−0.0014 (14)

0.0029 (13)

0.0019 (13)

−0.0010 (12)

0.0045 (17)

0.0019 (11)

0.0012 (11)

0.0028 (13)

−0.0017 (12)

0.0008 (12)

0.0028 (12)

0.0168 (10)

0.0436 (13)

−0.0596 (17)

0.0581 (17)

−0.0291 (18)

−0.0028 (10)

0.0052 (9)

C10

C11

C12

C13

C14

C15

C16

C17

C18

C19

C20

C21

C22

C23

C24

C25

C26

C27

F1

F2

F3

F4

F5

F6

N1

N2

O1

0.0375 (18)

0.0294 (17)

0.0306 (16)

0.050 (2)

0.0223 (14)

0.0226 (15)

0.0363 (18)

0.0289 (16)

0.0214 (15)

0.0270 (16)

0.0628 (13)

0.0861 (17)

0.0528 (15)

0.0626 (17)

0.099 (2)

0.0514 (14)

0.0227 (12)

0.0371 (17)

0.0261 (11)

0.0217 (10)

0.0290 (11)

0.0636 (18)

0.0329 (15)

0.0204 (4)

0.135 (2)

0.134 (3)

0.090 (2)

0.0825 (16)

0.0222 (12)

0.0588 (19)

0.0271 (10)

0.0298 (10)

0.0228 (10)

0.0484 (16)

0.083 (2)

0.0577 (14)

0.0226 (12)

0.0370 (15)

0.0322 (11)

0.0256 (10)

0.0318 (11)

0.0762 (19)

0.088 (2)

−0.0053 (12)

0.0045 (8)

−0.0017 (8)

0.0060 (8)

−0.0027 (14)

−0.0119 (14)

0.0024 (3)

O2

O3

O4

O5

0.0016 (8)

0.0012 (8)

0.0315 (14)

0.0222 (15)

0.0020 (3)

0.0120 (13)

0.0161 (16)

0.0017 (3)

S1

0.0228 (3)

0.0246 (3)

Geometric parameters (Å, º)

C1—N1

C1—C2

C1—H1A

C1—H1B

C2—C6

C2—C3

C3—O1

C3—C4

C4—C14

C4—C5

1.474 (3)

1.507 (3)

0.9900

C15—C20

1.400 (4)

C15—C16

C16—C17

C16—H16

C17—C18

C17—H17

C18—C19

C18—C21

C19—C20

C19—H19

1.402 (4)

1.370 (4)

0.9500

1.386 (4)

0.9500

1.383 (4)

1.491 (4)

1.379 (4)

0.9500

0.9900

1.339 (4)

1.501 (4)

1.230 (3)

1.486 (4)

1.348 (4)

1.502 (4)

Acta Cryst. (2018). C74, 1171-1179

sup-16

supporting information

C5—N1

1.469 (3)

0.9900

1.468 (4)

0.9500

1.396 (4)

1.398 (4)

1.384 (4)

0.9500

1.385 (4)

0.9500

1.384 (4)

1.491 (4)

1.385 (4)

0.9500

C20—H20

C21—F5

C21—F6

C21—F4

C22—C23

C22—C27

C22—S1

C23—C24

C23—H23

C24—C25

C24—H24

C25—C26

C25—N2

C26—C27

C26—H26

C27—H27

N1—S1

0.9500

C5—H5A

C5—H5B

C6—C7

C6—H6

C7—C8

C7—C12

C8—C9

C8—H8

C9—C10

C9—H9

C10—C11

C10—C13

C11—C12

C11—H11

C12—H12

C13—F3

C13—F1

C13—F2

C14—C15

C14—H14

1.310 (4)

1.325 (4)

1.331 (4)

1.390 (4)

1.391 (4)

1.775 (3)

1.385 (4)

0.9500

1.376 (4)

0.9500

1.376 (4)

1.481 (4)

1.381 (4)

0.9500

1.318 (4)

1.329 (4)

1.347 (4)

1.456 (4)

0.9500

1.635 (2)

1.222 (4)

1.224 (4)

1.4290 (19)

1.4246 (19)

N2—O5

N2—O4

O2—S1

O3—S1

N1—C1—C2

N1—C1—H1A

C2—C1—H1A

N1—C1—H1B

C2—C1—H1B

H1A—C1—H1B

C6—C2—C3

C6—C2—C1

C3—C2—C1

O1—C3—C4

O1—C3—C2

C4—C3—C2

C14—C4—C3

C14—C4—C5

C3—C4—C5

N1—C5—C4

N1—C5—H5A

C4—C5—H5A

N1—C5—H5B

C4—C5—H5B

H5A—C5—H5B

C2—C6—C7

C2—C6—H6

C7—C6—H6

C8—C7—C12

C8—C7—C6

107.8 (2)

110.1

C16—C15—C14

C17—C16—C15

C17—C16—H16

C15—C16—H16

C16—C17—C18

C16—C17—H17

C18—C17—H17

C19—C18—C17

C19—C18—C21

C17—C18—C21

C20—C19—C18

C20—C19—H19

C18—C19—H19

C19—C20—C15

C19—C20—H20

C15—C20—H20

F5—C21—F6

118.5 (3)

121.3 (3)

119.4

120.0 (3)

120.0

108.5

116.9 (2)

124.4 (2)

118.7 (2)

120.8 (2)

118.3 (2)

118.1 (2)

123.8 (2)

118.1 (2)

108.8 (2)

109.9

108.3

130.6 (2)

114.7

118.4 (2)

118.2 (2)

120.0

120.0 (3)

120.6 (3)

119.4 (3)

120.0 (3)

120.0

121.1 (3)

119.5

107.5 (3)

106.6 (3)

104.0 (3)

112.8 (3)

112.1 (3)

113.2 (3)

121.6 (3)

119.0 (2)

119.4 (2)

119.0 (3)

F5—C21—F4

F6—C21—F4

F5—C21—C18

F6—C21—C18

F4—C21—C18

C23—C22—C27

C23—C22—S1

C27—C22—S1

C24—C23—C22

Acta Cryst. (2018). C74, 1171-1179

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supporting information

C12—C7—C6

C9—C8—C7

C9—C8—H8

C7—C8—H8

C8—C9—C10

C8—C9—H9

C10—C9—H9

C11—C10—C9

C11—C10—C13

C9—C10—C13

C10—C11—C12

C10—C11—H11

C12—C11—H11

C11—C12—C7

C11—C12—H12

C7—C12—H12

F3—C13—F1

123.3 (2)

121.3 (3)

119.4

119.3 (3)

120.4

C24—C23—H23

C22—C23—H23

C25—C24—C23

C25—C24—H24

C23—C24—H24

C26—C25—C24

C26—C25—N2

C24—C25—N2

C25—C26—C27

C25—C26—H26

C27—C26—H26

C26—C27—C22

C26—C27—H27

C22—C27—H27

C5—N1—C1

C5—N1—S1

C1—N1—S1

O5—N2—O4

O5—N2—C25

O4—N2—C25

O3—S1—O2

O3—S1—N1

O2—S1—N1

120.5

118.6 (3)

120.7

123.0 (3)

118.6 (3)

118.4 (3)

118.7 (3)

120.7

119.1 (3)

120.5

120.4

120.6 (3)

119.9 (2)

119.4 (3)

119.9 (2)

120.0

120.6 (2)

119.7

120.5

111.8 (2)

116.02 (17)

119.59 (17)

124.4 (3)

117.5 (3)

118.1 (3)

120.83 (12)

106.37 (11)

107.05 (11)

107.42 (12)

107.99 (12)

106.35 (12)

119.7

107.2 (3)

106.5 (3)

104.8 (2)

112.9 (3)

113.8 (2)

111.1 (3)

129.4 (3)

115.3

F3—C13—F2

F1—C13—F2

F3—C13—C10

F1—C13—C10

F2—C13—C10

C4—C14—C15

C4—C14—H14

C15—C14—H14

C20—C15—C16

C20—C15—C14

O3—S1—C22

O2—S1—C22

N1—S1—C22

115.3

117.6 (3)

123.8 (2)

N1—C1—C2—C6

N1—C1—C2—C3

C6—C2—C3—O1

C1—C2—C3—O1

C6—C2—C3—C4

C1—C2—C3—C4

O1—C3—C4—C14

C2—C3—C4—C14

O1—C3—C4—C5

C2—C3—C4—C5

C14—C4—C5—N1

C3—C4—C5—N1

C3—C2—C6—C7

C1—C2—C6—C7

C2—C6—C7—C8

C2—C6—C7—C12

C12—C7—C8—C9

C6—C7—C8—C9

C7—C8—C9—C10

C8—C9—C10—C11

−149.6 (3)

29.4 (3)

−0.8 (4)

−180.0 (2)

−178.9 (2)

2.0 (4)

C17—C18—C19—C20

C21—C18—C19—C20

C18—C19—C20—C15

C16—C15—C20—C19

C14—C15—C20—C19

C19—C18—C21—F5

C17—C18—C21—F5

C19—C18—C21—F6

C17—C18—C21—F6

C19—C18—C21—F4

C17—C18—C21—F4

C27—C22—C23—C24

S1—C22—C23—C24

C22—C23—C24—C25

C23—C24—C25—C26

C23—C24—C25—N2

C24—C25—C26—C27

N2—C25—C26—C27

C25—C26—C27—C22

C23—C22—C27—C26

−1.0 (4)

−178.8 (3)

−0.8 (4)

2.8 (4)

178.4 (3)

−136.3 (3)

45.9 (4)

102.2 (4)

−75.6 (4)

−15.1 (5)

167.1 (3)

0.5 (4)

179.0 (2)

−0.8 (4)

0.9 (4)

−178.9 (2)

−0.8 (4)

179.0 (2)

0.5 (4)

0.1 (4)

178.2 (2)

−179.7 (2)

−1.6 (4)

149.9 (3)

−30.3 (3)

174.9 (2)

−6.0 (5)

154.6 (3)

−30.2 (4)

1.4 (4)

176.9 (3)

−1.5 (4)

0.5 (4)

−0.4 (4)

Acta Cryst. (2018). C74, 1171-1179

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supporting information

C8—C9—C10—C13

C9—C10—C11—C12

C13—C10—C11—C12

C10—C11—C12—C7

C8—C7—C12—C11

C6—C7—C12—C11

C11—C10—C13—F3

C9—C10—C13—F3

C11—C10—C13—F1

C9—C10—C13—F1

C11—C10—C13—F2

C9—C10—C13—F2

C3—C4—C14—C15

C5—C4—C14—C15

C4—C14—C15—C20

C4—C14—C15—C16

C20—C15—C16—C17

C14—C15—C16—C17

C15—C16—C17—C18

C16—C17—C18—C19

C16—C17—C18—C21

−175.5 (3)

0.6 (4)

S1—C22—C27—C26

C4—C5—N1—C1

C4—C5—N1—S1

C2—C1—N1—C5

C2—C1—N1—S1

C26—C25—N2—O5

C24—C25—N2—O5

C26—C25—N2—O4

C24—C25—N2—O4

C5—N1—S1—O3

C1—N1—S1—O3

C5—N1—S1—O2

C1—N1—S1—O2

C5—N1—S1—C22

C1—N1—S1—C22

C23—C22—S1—O3

C27—C22—S1—O3

C23—C22—S1—O2

C27—C22—S1—O2

C23—C22—S1—N1

C27—C22—S1—N1

−178.8 (2)

66.3 (3)

−151.72 (18)

−65.4 (3)

154.18 (18)

1.4 (4)

−178.8 (3)

−176.5 (3)

3.3 (4)

176.6 (2)

−0.7 (4)

−0.3 (4)

−175.5 (2)

150.4 (3)

−33.6 (4)

27.9 (4)

−156.0 (3)

−90.1 (3)

86.0 (3)

−175.3 (3)

4.5 (5)

27.5 (5)

−157.0 (3)

−3.1 (4)

−178.9 (3)

1.3 (4)

51.6 (2)

−169.49 (19)

−177.90 (18)

−39.0 (2)

−62.6 (2)

76.2 (2)

162.1 (2)

−19.4 (2)

30.3 (2)

−151.2 (2)

−84.4 (2)

94.1 (2)

0.7 (4)

178.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

C24—H24···O3ⁱ

C23—H23···O2ⁱⁱ

0.95

2.56

2.36

3.380 (4)

3.304 (3)

145

176

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2.

(3E,5E)-1-(4-Cyanobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane

monosolvate (7)

Crystal data

C₂₈H₁₈F₆N₂O₃S·CH₂Cl₂

M_r= 661.43

Triclinic, P1

Z = 2

F(000) = 672

D_x= 1.536 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 5958 reflections

θ = 2.6–26.5°

µ = 0.38 mm⁻¹

T = 150 K

Block, yellow

0.20 × 0.15 × 0.11 mm

a = 9.7338 (6) Å

b = 12.4558 (9) Å

c = 12.6397 (9) Å

α = 70.586 (3)°

β = 88.379 (4)°

γ = 81.726 (3)°

V = 1429.97 (17) Å³

Data collection

Bruker SMART CCD area detector

diffractometer

Radiation source: sealed tube

phi and ω scans

24790 measured reflections

5604 independent reflections

3869 reflections with I > 2σ(I)

R_int= 0.070

Acta Cryst. (2018). C74, 1171-1179

sup-19

supporting information

θ

_max= 26.0°, θ_min= 2.6°

k = −15→15

l = −15→15

h = −12→12

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.046

wR(F²) = 0.109

S = 1.00

5604 reflections

388 parameters

0 restraints

Hydrogen site location: inferred from

neighbouring sites

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0465P)²+ 0.7221P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max< 0.001

Δρ_max= 0.53 e Å⁻³

Δρ_min= −0.44 e Å⁻³

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full

covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and

torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.

An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

C1

0.2251 (3)

0.3181

0.1587

0.2295 (2)

0.1347 (3)

0.0349 (2)

0.0378 (2)

−0.0243

0.6874 (2)

0.7010

0.7048

0.5639 (2)

0.5379 (2)

0.6341 (2)

0.7528 (2)

0.7657

0.3737 (2)

0.3429

0.3104

0.4483 (2)

0.5467 (2)

0.5613 (2)

0.4781 (2)

0.4131

0.0239 (6)

0.029*

0.0203 (5)

0.0228 (6)

0.0203 (5)

0.0221 (5)

0.027*

H1A

H1B

C2

C3

C4

C5

H5A

H5B

C6

0.0057

0.3168 (2)

0.3107

0.8116

0.4754 (2)

0.4028

0.5136

0.4360 (2)

0.4912

0.027*

0.0222 (6)

0.027*

H6

C7

C8

H8

0.4201 (2)

0.5350 (3)

0.5408

0.4745 (2)

0.3884 (2)

0.3317

0.3497 (2)

0.3780 (2)

0.4505

0.0214 (5)

0.0239 (6)

0.029*

C9

H9

0.6399 (3)

0.7181

0.3837 (2)

0.3254

0.3037 (2)

0.3255

0.0249 (6)

0.030*

C10

C11

H11

C12

H12

C13

C14

H14

C15

C16

H16

C17

0.6306 (3)

0.5137 (3)

0.5054

0.4095 (3)

0.3300

0.7436 (3)

−0.0505 (3)

−0.0352

−0.1642 (2)

−0.2007 (3)

−0.1463

0.4647 (2)

0.5474 (2)

0.6010

0.5524 (2)

0.6092

0.4651 (2)

0.6104 (2)

0.5338

0.6869 (2)

0.6650 (2)

0.6056

0.1966 (2)

0.1649 (2)

0.0908

0.2400 (2)

0.2172

0.1152 (2)

0.6484 (2)

0.6993

0.6756 (2)

0.7880 (2)

0.8451

0.0230 (6)

0.0253 (6)

0.030*

0.0238 (6)

0.029*

0.0306 (6)

0.0238 (6)

0.029*

0.0232 (6)

0.0318 (6)

0.038*

−0.3144 (3)

0.7282 (3)

0.8170 (2)

0.0348 (7)

Acta Cryst. (2018). C74, 1171-1179

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supporting information

H17

C18

C19

H19

C20

H20

C21

C22

C23

H23

C24

H24

C25

C26

H26

C27

H27

C28

C29

H29A

H29B

Cl1

Cl2

F1

−0.3365

0.7136

0.8937

0.042*

−0.3965 (3)

−0.3622 (3)

−0.4180

−0.2459 (2)

−0.2213

−0.5244 (3)

0.1465 (2)

0.1993 (3)

0.2846

0.1271 (3)

0.1629

0.0013 (3)

−0.0518 (3)

−0.1380

0.0212 (3)

−0.0140

−0.0742 (3)

0.3476 (3)

0.4133

0.8132 (2)

0.8373 (2)

0.8960

0.7755 (2)

0.7936

0.8746 (3)

0.9772 (2)

0.9807 (2)

0.9350

1.0512 (2)

1.0550

1.1169 (2)

1.1122 (2)

1.1568

1.0423 (2)

1.0388

1.1910 (3)

0.2120 (3)

0.1976

0.7342 (2)

0.6225 (2)

0.5658

0.5939 (2)

0.5174

0.7680 (3)

0.2868 (2)

0.1829 (2)

0.1780

0.0868 (2)

0.0152

0.0953 (2)

0.1996 (2)

0.2048

0.2959 (2)

0.3676

−0.0048 (3)

0.7732 (2)

0.7166

0.0278 (6)

0.0275 (6)

0.033*

0.0246 (6)

0.030*

0.0353 (7)

0.0199 (5)

0.0257 (6)

0.031*

0.0319 (6)

0.038*

0.0294 (6)

0.0303 (6)

0.036*

0.0264 (6)

0.032*

0.0447 (8)

0.0421 (8)

0.050*

0.3169

0.2960

0.7507

0.050*

0.20281 (8)

0.43281 (8)

0.80484 (18)

0.69830 (18)

0.84560 (17)

−0.60578 (18)

−0.49708 (16)

−0.60193 (18)

0.1814 (2)

−0.1347 (3)

0.1362 (2)

0.38056 (16)

0.19401 (18)

0.23658 (6)

0.14143 (7)

0.16459 (7)

0.56012 (16)

0.46293 (18)

0.37668 (15)

0.9403 (2)

0.94232 (15)

0.80030 (17)

0.76125 (17)

1.2483 (3)

0.43929 (15)

0.86676 (15)

0.92877 (15)

0.88541 (5)

0.77593 (7)

0.90498 (7)

0.08932 (16)

0.01714 (14)

0.15218 (14)

0.68140 (16)

0.82446 (15)

0.83699 (19)

0.44130 (16)

−0.0848 (2)

0.61050 (15)

0.38543 (14)

0.49955 (14)

0.41058 (5)

0.0483 (2)

0.0445 (2)

0.0527 (5)

0.0535 (5)

0.0473 (5)

0.0634 (6)

0.0434 (4)

0.0636 (6)

0.0208 (5)

0.0687 (10)

0.0326 (5)

0.0261 (4)

0.0278 (4)

0.02072 (15)

F2

F3

F4

F5

F6

N1

N2

O1

O2

O3

S1

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

C1

C2

C3

C4

C5

C6

C7

C8

C9

0.0293 (14)

0.0221 (12)

0.0272 (14)

0.0225 (13)

0.0219 (13)

0.0262 (13)

0.0247 (13)

0.0275 (14)

0.0245 (13)

0.0212 (14)

0.0201 (13)

0.0213 (14)

0.0215 (13)

0.0204 (13)

0.0190 (13)

0.0189 (13)

0.0222 (14)

0.0231 (14)

0.0206 (13)

−0.0014 (11)

−0.0031 (10)

−0.0073 (11)

−0.0061 (10)

−0.0039 (10)

−0.0050 (11)

−0.0053 (11)

−0.0037 (11)

0.0003 (11)

0.0024 (11)

−0.0042 (10)

−0.0010 (11)

−0.0003 (10)

0.0017 (10)

−0.0051 (10)

−0.0042 (10)

−0.0038 (11)

−0.0047 (11)

−0.0073 (11)

−0.0048 (10)

−0.0059 (11)

−0.0058 (11)

−0.0027 (11)

−0.0035 (11)

−0.0073 (11)

−0.0036 (11)

−0.0066 (11)

0.0180 (12)

0.0206 (13)

0.0174 (12)

0.0210 (13)

0.0201 (13)

0.0220 (13)

0.0199 (13)

0.0251 (14)

Acta Cryst. (2018). C74, 1171-1179

sup-21

Article Doi

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(Arylidene)-N-benzene-sulfonyl-4-piperidone derivatives

DOI: 10.1107/S2053229618013232

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Article abstract of DOI:10.1107/S2053229618013232

Full text of DOI:10.1107/S2053229618013232

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