Hydrogen bonding in cyclic imides and amide carb-oxy-lic acid derivatives from the facile reaction of cis-cyclo-hexane-1,2-carb-oxy-lic anhydride with o- and p-anisidine and m- and p-amino-benzoic acids

Article abstract of DOI:10.1107/S0108270112030168

The structures of the open-chain amide carb-oxy-lic acid rac-cis-2-[(2-meth-oxy-phen-yl)carbamo-yl]cyclo-hexane-1-carb-oxy-lic acid, C₁₅H₁₉NO₄, (I), and the cyclic imides rac-cis-2-(4-meth-oxy-phen-yl)-3a,4,5,6,7,7a-hexa-hydro-isoindole-1,3-dione, C₁₅H₁₇NO₃, (II), chiral cis-3-(1,3-dioxo-3a,4, 5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, C₁₅H ₁₅NO₄, (III), and rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a- hexahydroisoindol-2-yl)benzoic acid monohydrate, C₁₅H ₁₅NO₄·H₂O, (IV), are reported. In the amide acid (I), the phenyl-carbamoyl group is essentially planar [maximum deviation from the least-squares plane = 0.060 (1) A for the amide O atom] and the mol-ecules form discrete centrosymmetric dimers through inter-molecular cyclic carbox-y-carboxy O - H...O hydrogen-bonding inter-actions [graph-set notation R 2 ²(8)]. The cyclic imides (II)-(IV) are conformationally similar, with comparable benzene ring rotations about the imide N - Car bond [dihedral angles between the benzene and isoindole rings = 51.55 (7)° in (II), 59.22 (12)° in (III) and 51.99 (14)° in (IV)]. Unlike (II), in which only weak inter-molecular C - H...Oimide hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong inter-molecular carb-oxy-lic acid O - H...O hydrogen-bonding associations. With (III), these involve imide O-atom acceptors, giving one-dimensional zigzag chains [graph-set C(9)], while with the monohydrate (IV), the hydrogen bond involves the partially disordered water mol-ecule which also bridges mol-ecules through both imide and carboxy O-atom acceptors in a cyclic R 4 ⁴(12) association, giving a two-dimensional sheet structure. The structures reported here expand the structural database for compounds of this series formed from the facile reaction of cis-cyclo-hexane-1,2-dicarb-oxy-lic anhydride with substituted anilines, in which there is a much larger incidence of cyclic imides compared to amide carb-oxy-lic acids.

Full text of DOI:10.1107/S0108270112030168

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
Comment
The 1:1 stoichiometric reaction of cis-cyclohexane-1,2-dicar-
boxylic anhydride (cis-CHDC anhydride) with substituted
anilines has been found to give both open-chain amide carb-
oxylic acids or more commonly cyclic imides under mild
reaction conditions (Smith & Wermuth, 2012a). These
products are analogous to the phthalanilic acids and phthal-
imides formed in the reactions of phthalic anhydride with
anilines (Perry & Parveen, 2001). We previously reported the
structure of the amide acid from the reaction of cis-CHDC
anhydride with 3-fluoroaniline and the isomeric cyclic imides
from the parallel reactions with 2- and 4-fluoroaniline (Smith
& Wermuth, 2012a), which are among only the very few
crystallographically characterized examples of these com-
pounds.
ISSN 0108-2701
Hydrogen bonding in cyclic imides
and amide carboxylic acid derivatives
from the facile reaction of cis-cyclo-
hexane-1,2-carboxylic anhydride
with o- and p-anisidine and m- and
p-aminobenzoic acids
Graham Smith* and Urs D. Wermuth
Science and Engineering Faculty, Queensland University of Technology, GPO Box
2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au
Received 14 June 2012
Accepted 2 July 2012
Online 1 August 2012
The structures of the open-chain amide carboxylic acid rac-
cis-2-[(2-methoxyphenyl)carbamoyl]cyclohexane-1-carboxylic
acid, C15H19NO4, (I), and the cyclic imides rac-cis-2-(4-
methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione,
C15H17NO3, (II), chiral cis-3-(1,3-dioxo-3a,4,5,6,7,7a-hexa-
hydroisoindol-2-yl)benzoic acid, C15H15NO4, (III), and rac-
cis-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic
acid monohydrate, C15H15NO4ꢀH2O, (IV), are reported. In
the amide acid (I), the phenylcarbamoyl group is essentially
planar [maximum deviation from the least-squares plane =
˚
0.060 (1) A for the amide O atom] and the molecules form
discrete centrosymmetric dimers through intermolecular
cyclic carboxy–carboxy O—Hꢀ ꢀ ꢀO hydrogen-bonding inter-
actions [graph-set notation R22(8)]. The cyclic imides (II)–
(IV) are conformationally similar, with comparable benzene
ring rotations about the imide N—Car bond [dihedral angles
between the benzene and isoindole rings = 51.55 (7)ꢁ in (II),
59.22 (12)ꢁ in (III) and 51.99 (14)ꢁ in (IV)]. Unlike (II), in
which only weak intermolecular C—Hꢀ ꢀ ꢀOimide hydrogen
bonding is present, the crystal packing of imides (III) and
(IV) shows strong intermolecular carboxylic acid O—Hꢀ ꢀ ꢀO
hydrogen-bonding associations. With (III), these involve
imide O-atom acceptors, giving one-dimensional zigzag
chains [graph-set C(9)], while with the monohydrate (IV),
the hydrogen bond involves the partially disordered water
molecule which also bridges molecules through both imide
and carboxy O-atom acceptors in a cyclic R44(12) association,
giving a two-dimensional sheet structure. The structures
reported here expand the structural database for compounds
of this series formed from the facile reaction of cis-
cyclohexane-1,2-dicarboxylic anhydride with substituted
anilines, in which there is a much larger incidence of cyclic
imides compared to amide carboxylic acids.
The parallel reaction of 2-methoxyaniline (o-anisidine),
4-methoxyaniline (p-anisidine), 3-carboxyaniline (m-amino-
benzoic acid) and 4-carboxyaniline (p-aminobenzoic acid)
with cis-CHDC anhydride under common mild reaction
conditions in 50% ethanol–water solution yielded, respec-
tively, the open-chain amide carboxylic acid racemic cis-2-
[(2-methoxyphenyl)carbamoyl]cyclohexane-1-carboxylic acid,
(I), and the cyclic imides racemic 2-(4-methoxyphenyl)-
3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione, (II), chiral 3-(1,3-
dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, (III),
and racemic 4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-
yl)benzoic acid monohydrate, (IV) (Figs. 1–4), and the struc-
tures are reported here.
Acta Cryst. (2012). C68, o327–o331
doi:10.1107/S0108270112030168
# 2012 International Union of Crystallography o327

organic compounds
Figure 3
The molecular conformation and atom-labelling scheme for (III).
Displacement ellipsoids are drawn at the 40% probability level.
Figure 1
The molecular conformation and atom-labelling scheme for (I).
Displacement ellipsoids are drawn at the 40% probability level.
Figure 2
The molecular conformation and atom-labelling scheme for (II).
Displacement ellipsoids are drawn at the 40% probability level.
In the racemic amide acid (I) (Fig. 1), the phenylcarbamoyl
group is essentially planar [C21—C11—N11—C12 torsion
angle = 175.18 (12)ꢁ], with a maximum deviation from the
Figure 4
The molecular conformation and atom-labelling scheme for (IV).
Displacement ellipsoids are drawn at the 40% probability level. The
water molecule of solvation is disordered over two sites [O1W, occupancy
factor = 0.81 (1); O2W, occupancy factor = 0.19 (1)]. Inter-species
hydrogen bonds are shown as dashed lines.
˚
least-squares plane of 0.060 (1) A for the amide O atom.
The conformation is stabilized by intramolecular N11—
Hꢀ ꢀ ꢀO211(methoxy) and aromatic C61—Hꢀ ꢀ ꢀO12(carbonyl)
˚
interactions [Hꢀ ꢀ ꢀO = 2.6003 (14) and 2.8812 (17) A, respec-
59.22 (12) and 51.99 (14)ꢁ, respectively, between the benzene
ring and the plane of the isoindole ring, in which distortion
results in either atom C8 or C9 showing a maximum deviation
of 0.157 (1) A in (II), 0.139 (2) A in (III) and 0.131 (3) A in
(IV). These values compare closely to those of 0.152 (1) and
˚
0.149 (1) A for the 2- and 4-fluoro analogues, respectively
˚
(Smith & Wermuth, 2012a), and 0.153 (3) and 0.138 (4) A for
the 4-bromo- and 3-carboxy-4-hydroxy-substituted analogues,
respectively (Smith & Wermuth, 2012b). In (III) and (IV), the
carboxy substituent groups are close to being coplanar with
tively]. The carboxy group on the cyclohexane ring is almost
parallel to the C1—C3 bond [C1—C2—C22—O22 torsion
angle = 173.17 (10)ꢁ] and the methoxy group is close to being
coplanar with the benzene ring [C11—C21—O211—C211
torsion angle = 173.23 (11)ꢁ]. The molecules form discrete
centrosymmetric dimers through classical intermolecular
cyclic carboxy–carboxy O—Hꢀ ꢀ ꢀO hydrogen-bonding inter-
actions (Table 1) [graph-set notation R22(8); Etter et al., 1990]
(Fig. 5). The amide group is not involved in intermolecular
interactions, which is unlike the 4-chloro-substituted analogue
in which the amide group links hydrogen-bonded carboxylic
acid chains into a two-dimensional sheet structure (Smith &
Wermuth, 2012b).
˚
˚
˚
the attached benzene rings [C21—C31—C311—O32
=
ꢂ172.2 (2)ꢁ in (III) and C31—C41—C411—O42 = ꢂ177.3 (3)ꢁ
in (IV)].
Unlike the structure of (II), in which there are only weak
aromatic C—Hꢀ ꢀ ꢀOimide hydrogen-bonding interactions
(Table 2), the crystal packing of both imides (III) and (IV)
shows strong intermolecular O—Hꢀ ꢀ ꢀO hydrogen-bonding
interactions involving carboxy groups. In (III), these are with
imide O-atom acceptors (Table 3), giving one-dimensional
zigzag chains [C(9)] which extend along (010) (Fig. 6). In the
monohydrate (IV), the para-carboxy group forms a hydrogen
bond with the partially disordered water molecule [O1W,
The cyclic imides (II) and (IV) (Figs. 2 and 4) are racemic,
while compound (III) is chiral. However, the absolute
configurations for the two chiral centres in (III) were not
determined, being arbitrarily assigned (C8S and C9R).
Conformationally, compounds (II)–(IV) are similar, with
comparable ring rotations about the imide N—Car bond
[minimum torsion angles C1/C3—N2—C11—C21
=
ꢂ56.72 (18)ꢁ for (II), 61.8 (3)ꢁ for (III) and ꢂ53.8 (3)ꢁ for
(IV)]. These correspond to dihedral angles of 51.55 (7),
ꢃ
o328 Smith and Wermuth C15H19NO4, C15H17NO3, C15H15NO4 and C15H15NO4ꢀH2O
Acta Cryst. (2012). C68, o327–o331

organic compounds
Figure 7
The two-dimensional hydrogen-bonded structure in (IV), viewed
approximately down the a-cell direction of the unit cell, showing
hydrogen-bonding interactions as dashed lines. Non-associative H atoms
have been omitted as has the minor-component O2W water molecule. For
symmetry codes, see Table 4.
Figure 5
The centrosymmetric hydrogen-bonded dimers in the structure of (I),
showing hydrogen-bonding interactions as dashed lines. Non-associative
H atoms have been omitted. For symmetry code (i), see Table 1.
The structures reported here expand the structural database
for compounds of this series, formed in the facile reaction of
cis-CHDC anhydride with substituted anilines, among which
there is a much larger incidence of cyclic imides compared to
amide carboxylic acids [currently 8:3, among known examples,
which, apart from our previously reported structures, include
the imide from the reaction with 5-benzyloxy-2,4-dichloro-
aniline (Wang et al., 2005) and those from the reactions with
4-bromoaniline and 5-aminosalicylic acid (Smith & Wermuth,
2012b)]. However, there are no apparent structural features
which might allow a definitive prediction of the preferred
reaction product.
Experimental
The title compounds were synthesized by heating together under
reflux for 15 min 1 mmol quantities of cis-cyclohexane-1,2-dicarb-
oxylic anhydride and o-anisidine [for (I)], p-anisidine [for (II)], m-
aminobenzoic acid [for (III)] and p-aminobenzoic acid [for (IV)] in
ethanol–water (50 ml, 1:1 v/v). After volume reduction to 30 ml, the
hot-filtered solutions were allowed to evaporate to incipient dryness
at room temperature over a period of several weeks, giving either
colourless plates [of (I)–(III)] or fine needles [of (IV)] from which
specimens were cleaved for structural analyses.
Figure 6
The one-dimensional hydrogen-bonded chain structures in (III), viewed
down the a-cell direction of the unit cell, showing hydrogen-bonding
interactions as dashed lines. Non-associative H atoms have been omitted.
For symmetry code (i), see Table 3.
Compound (I)
Crystal data
C15H19NO4
Mr = 277.31
Triclinic, P1
a = 7.3557 (4) A
˚
b = 8.3630 (4) A
c = 11.7128 (6) A
ꢀ = 100.453 (4)ꢁ
ꢁ = 97.232 (4)ꢁ
ꢂ = 104.042 (4)ꢁ
3
˚
V = 676.40 (6) A
Z = 2
occupancy factor = 0.81 (1); O2W, occupancy factor =
0.19 (1)], both components of which also act as donors to both
imide and carboxy O-atom acceptors (Table 4). These inter-
actions give an R44(12) ring motif and extend the structure into
a two-dimensional sheet (Fig. 7).
˚
Mo Kꢀ radiation
ꢃ = 0.10 mmꢂ1
T = 200 K
0.45 ꢄ 0.30 ꢄ 0.18 mm
˚
ꢃ
Acta Cryst. (2012). C68, o327–o331
Smith and Wermuth
C15H19NO4, C15H17NO3, C15H15NO4 and C15H15NO4ꢀH2O o329

organic compounds
Table 1
Hydrogen-bond geometry (A, ) for (I).
Table 2
Hydrogen-bond geometry (A, ) for (II).
ꢁ
ꢁ
˚
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
O22—H22ꢀ ꢀ ꢀO21i
Symmetry code: (i) ꢂx; ꢂy þ 1; ꢂz þ 1.
0.94 (2)
1.76 (2)
2.6866 (14)
173 (2)
C21—H21ꢀ ꢀ ꢀO3i
0.93
0.93
2.56
2.46
3.2205 (15)
3.2914 (17)
128
149
C51—H51ꢀ ꢀ ꢀO1ii
3
2
1
2
1
2
Symmetry codes: (i) x; y þ 1; z; (ii) ꢂx þ ; y ꢂ ; ꢂz þ .
Table 3
Hydrogen-bond geometry (A, ) for (III).
Data collection
ꢁ
˚
Oxford Diffraction Gemini-S CCD-
detector diffractometer
Absorption correction: multi-scan
(CrysAlis PRO; Oxford
Diffraction, 2010)
8079 measured reflections
2640 independent reflections
2082 reflections with I > 2ꢄ(I)
Rint = 0.024
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
O31—H31ꢀ ꢀ ꢀO1i
Symmetry code: (i) ꢂx þ 1; y þ ; ꢂz þ .
0.89 (3)
1.84 (3)
2.682 (2)
156 (3)
1
2
3
2
Tmin = 0.975, Tmax = 0.980
Refinement
Table 4
Hydrogen-bond geometry (A, ) for (IV).
R[F2 > 2ꢄ(F2)] = 0.035
wR(F2) = 0.087
S = 1.03
2640 reflections
189 parameters
H atoms treated by a mixture of
independent and constrained
refinement
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
ꢂ3
˚
Áꢅmax = 0.18 e A
ꢂ3
˚
O41—H41ꢀ ꢀ ꢀO1Wi
O1W—H11Wꢀ ꢀ ꢀO1
O1W—H12Wꢀ ꢀ ꢀO42ii
O2W—H21Wꢀ ꢀ ꢀO1
O2W—H22Wꢀ ꢀ ꢀO42iii
0.90
0.83
0.82
0.90
0.90
1.71
2.08
1.94
2.10
2.33
2.609 (3)
2.894 (3)
2.754 (3)
2.991 (12)
3.233 (12)
179
167
172
179
178
Áꢅmin = ꢂ0.20 e A
Compound (II)
1
2
1
2
1
2
3
1
3
2
1
2
Symmetry codes: (i) x ꢂ ; ꢂy ꢂ ; z þ ; (ii) ꢂx þ ; y ꢂ ; ꢂz þ ; (iii) x þ ,
2
2
Crystal data
1
2
1
2
ꢂy þ ; z ꢂ .
3
˚
V = 1273.42 (11) A
Z = 4
C15H17NO3
Mr = 259.30
Monoclinic, P21=n
Mo Kꢀ radiation
ꢃ = 0.09 mmꢂ1
T = 200 K
0.40 ꢄ 0.25 ꢄ 0.12 mm
˚
a = 11.7119 (5) A
Refinement
˚
b = 6.6705 (3) A
R[F2 > 2ꢄ(F2)] = 0.038
wR(F2) = 0.086
S = 1.10
1728 reflections
185 parameters
H atoms treated by a mixture of
independent and constrained
refinement
˚
c = 17.2898 (8) A
ꢁ = 109.482 (5)ꢁ
ꢂ3
˚
Áꢅmax = 0.18 e A
ꢂ3
Data collection
˚
Áꢅmin = ꢂ0.18 e A
Oxford Diffraction Gemini-S CCD-
detector diffractometer
Absorption correction: multi-scan
(CrysAlis PRO; Oxford
Diffraction, 2010)
8552 measured reflections
2498 independent reflections
1959 reflections with I > 2ꢄ(I)
Rint = 0.024
Compound (IV)
Crystal data
Tmin = 0.929, Tmax = 0.981
3
˚
V = 1419.6 (3) A
Z = 4
C15H15NO4ꢀH2O
Mr = 291.30
Monoclinic, P21=n
Refinement
Mo Kꢀ radiation
ꢃ = 0.10 mmꢂ1
T = 200 K
0.30 ꢄ 0.10 ꢄ 0.08 mm
R[F2 > 2ꢄ(F2)] = 0.035
wR(F2) = 0.088
S = 1.09
172 parameters
H-atom parameteꢂrs3 constrained
˚
˚
a = 13.077 (2) A
b = 6.6713 (7) A
˚
Áꢅmax = 0.18 e A
˚
c = 16.432 (2) A
ꢂ3
˚
2498 reflections
Áꢅmin = ꢂ0.17 e A
ꢁ = 97.982 (13)ꢁ
Data collection
Compound (III)
Oxford Diffraction Gemini-S CCD-
detector diffractometer
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffrac-
tion, 2010)
9649 measured reflections
2790 independent reflections
1374 reflections with I > 2ꢄ(I)
Rint = 0.055
Crystal data
3
˚
V = 1312.03 (8) A
Z = 4
Mo Kꢀ radiation
ꢃ = 0.10 mmꢂ1
T = 200 K
C15H15NO4
Mr = 273.28
Orthorhombic, P212121
Tmin = 0.813, Tmax = 0.980
˚
a = 6.4958 (2) A
b = 12.5236 (4) A
˚
c = 16.1281 (6) A
˚
Refinement
0.45 ꢄ 0.12 ꢄ 0.08 mm
R[F2 > 2ꢄ(F2)] = 0.052
wR(F2) = 0.132
S = 0.85
194 parameters
H-atom parameteꢂrs3 constrained
Data collection
˚
Áꢅmax = 0.34 e A
Áꢅmin = ꢂ0.20 e A
Oxford Diffraction Gemini-S Ultra
CCD-detector diffractometer
Absorption correction: multi-scan
(CrysAlis PRO; Oxford
4693 measured reflections
1728 independent reflections
1395 reflections with I > 2ꢄ(I)
Rint = 0.024
ꢂ3
˚
2790 reflections
Amide and/or carboxylic acid H atoms in (I), (III) and (IV) were
located by difference methods and in (I) and (III) both their posi-
Diffraction, 2010)
Tmin = 0.980, Tmax = 0.990
ꢃ
o330 Smith and Wermuth C15H19NO4, C15H17NO3, C15H15NO4 and C15H15NO4ꢀH2O
Acta Cryst. (2012). C68, o327–o331

organic compounds
tional and isotropic displacement parameters were refined. For (IV),
these H atoms were allowed to ride in the refinement, with Uiso(H) =
1.5Ueq(O). Other H atoms in all structures were allowed to ride in the
refinement, with Uiso(H) = 1.2Ueq(O). Other H atoms in all structures
were included in the respective refinements at calculated positions
The authors acknowledge financial support from the
Australian Research Council and the Science and Engineering
Faculty, Queensland University of Technology.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: BM3120). Services for accessing these data are
described at the back of the journal.
˚
(C—H = 0.93–0.98 A), with Uiso(H) = 1.2Ueq(C), using a riding-model
approximation. The water molecule of solvation in (IV) was found to
˚
be disordered over two adjacent sites [Oꢀ ꢀ ꢀO = 1.458 (12) A], with
occupancy factors determined as 0.81 (1) (O1W) and 0.19 (1) (O2W).
The occupancies were subsequently fixed and the minor component
was refined isotropically. In chiral (III), in the absence of a suitable
heavy atom, Friedel pairs (1062) were merged, the relative config-
uration of the chiral centres (C8S and C9R) being arbitrarily
assigned.
References
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl.
Cryst. 26, 343–350.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–
262.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton,
Oxfordshire, England.
Perry, C. J. & Parveen, Z. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 512–521.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Smith, G. & Wermuth, U. D. (2012a). Acta Cryst. C68, o253–o256.
Smith, G. & Wermuth, U. D. (2012b). J. Chem. Crystallogr. In the press.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
For all compounds, data collection: CrysAlis PRO (Oxford
Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction:
CrysAlis PRO. Program(s) used to solve structure: SIR92 (Altomare
et al., 1993) for (I), (III) and (IV); SHELXS97 (Sheldrick, 2008) for
(II). For all compounds, program(s) used to refine structure:
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999);
molecular graphics: PLATON (Spek, 2009); software used to prepare
material for publication: PLATON.
Wang, N.-X., Luo, Y.-P., Chen, Q. & Yang, G.-F. (2005). Acta Cryst. E61,
o2081–o2082.
ꢃ
Acta Cryst. (2012). C68, o327–o331
Smith and Wermuth
C15H19NO4, C15H17NO3, C15H15NO4 and C15H15NO4ꢀH2O o331

supplementary materials
supplementary materials
Acta Cryst. (2012). C68, o327–o331 [doi:10.1107/S0108270112030168]
Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from
the facile reaction of cis-cyclohexane-1,2-carboxylic anhydride with o- and p-
anisidine and m- and p-aminobenzoic acids
Graham Smith and Urs D. Wermuth
(I) 2-[(2-methoxyphenyl)carbamoyl]cyclohexane-1-carboxylic acid
Crystal data
C15H19NO4
Z = 2
Mr = 277.31
Triclinic, P1
F(000) = 296
Dx = 1.362 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4313 reflections
θ = 3.3–28.8°
Hall symbol: -P 1
a = 7.3557 (4) Å
b = 8.3630 (4) Å
c = 11.7128 (6) Å
α = 100.453 (4)°
β = 97.232 (4)°
γ = 104.042 (4)°
V = 676.40 (6) Å3
µ = 0.10 mm−1
T = 200 K
Flat prism, colourless
0.45 × 0.30 × 0.18 mm
Data collection
Oxford Diffraction Gemini-S CCD-detector
diffractometer
Radiation source: Enhance (Mo) X-ray source
Graphite monochromator
Detector resolution: 16.077 pixels mm-1
ω scans
8079 measured reflections
2640 independent reflections
2082 reflections with I > 2σ(I)
Rint = 0.024
θmax = 26.0°, θmin = 3.3°
h = −9→9
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = −10→10
l = −14→14
T
min = 0.975, Tmax = 0.980
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.035
wR(F2) = 0.087
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.03
2640 reflections
189 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0513P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.20 e Å−3
Acta Cryst. (2012). C68, o327–o331
sup-1

supplementary materials
Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are
estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the
estimation of distances, angles and torsion angles
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O12
O21
O22
O211
N11
C1
−0.14926 (13)
0.08493 (13)
0.01483 (14)
0.19154 (12)
0.04741 (16)
0.18449 (16)
0.13519 (16)
0.30154 (18)
0.48581 (17)
0.53572 (17)
0.37447 (17)
−0.08286 (17)
0.01120 (17)
−0.00335 (18)
0.07697 (16)
−0.12003 (19)
−0.3160 (2)
−0.39563 (19)
−0.27918 (18)
0.2820 (2)
0.20390
0.07111 (14)
0.41630 (11)
0.29940 (13)
0.36885 (11)
0.20455 (13)
0.13300 (15)
0.14141 (14)
0.12408 (16)
0.25512 (16)
0.24351 (17)
0.25898 (16)
0.22259 (15)
0.13474 (15)
0.31266 (15)
0.29933 (15)
0.34059 (16)
0.27757 (17)
0.18700 (16)
0.15905 (16)
0.44485 (18)
0.02080
0.19578 (9)
0.38713 (8)
0.53760 (8)
−0.06244 (8)
0.08805 (9)
0.26727 (10)
0.39152 (10)
0.47820 (11)
0.47911 (11)
0.35632 (12)
0.26619 (11)
−0.00513 (10)
0.18109 (11)
−0.08506 (11)
0.43665 (10)
−0.17739 (11)
−0.19104 (12)
−0.11428 (12)
−0.02087 (11)
−0.14755 (13)
0.24310
0.0449 (4)
0.0321 (3)
0.0375 (4)
0.0318 (3)
0.0258 (3)
0.0213 (4)
0.0211 (4)
0.0267 (4)
0.0282 (4)
0.0316 (4)
0.0259 (4)
0.0235 (4)
0.0236 (4)
0.0248 (4)
0.0219 (4)
0.0301 (4)
0.0322 (4)
0.0314 (4)
0.0284 (4)
0.0378 (5)
0.0260*
C2
C3
C4
C5
C6
C11
C12
C21
C22
C31
C41
C51
C61
C211
H1
H2
0.02610
0.04440
0.38650
0.0250*
H3A
H3B
H4A
H4B
H5A
H5B
H6A
H6B
H11
H21A
H21B
H21C
H22
H31
H41
H51
0.27110
0.13760
0.55700
0.0320*
0.31850
0.01190
0.45580
0.0320*
0.58840
0.23800
0.53200
0.0340*
0.47270
0.36720
0.50840
0.0340*
0.56310
0.13610
0.33090
0.0380*
0.64970
0.33270
0.35930
0.0380*
0.40640
0.23830
0.18800
0.0310*
0.36120
0.37300
0.28410
0.0310*
0.164 (2)
0.2508 (18)
0.47850
0.0824 (13)
−0.12170
0.045 (4)*
0.0450*
0.41750
0.23900
0.54230
−0.15640
0.0450*
0.25030
0.36500
−0.22190
0.0450*
−0.015 (3)
−0.06730
0.402 (3)
0.5587 (17)
−0.23000
0.082 (6)*
0.0360*
0.40120
−0.39450
0.29680
−0.25280
0.0390*
−0.52710
0.14440
−0.12470
0.0380*
Acta Cryst. (2012). C68, o327–o331
sup-2

supplementary materials
H61
−0.33300
0.09770
0.03110
0.0340*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O12
O21
O22
O211
N11
C1
0.0229 (5)
0.0487 (6)
0.0604 (7)
0.0295 (5)
0.0217 (6)
0.0237 (6)
0.0231 (6)
0.0336 (7)
0.0280 (7)
0.0220 (7)
0.0237 (6)
0.0272 (7)
0.0236 (6)
0.0294 (7)
0.0197 (6)
0.0430 (8)
0.0392 (8)
0.0275 (7)
0.0287 (7)
0.0412 (8)
0.0766 (8)
0.0297 (5)
0.0392 (6)
0.0369 (5)
0.0309 (6)
0.0200 (6)
0.0189 (6)
0.0246 (7)
0.0273 (7)
0.0364 (8)
0.0308 (7)
0.0222 (6)
0.0245 (7)
0.0217 (6)
0.0288 (7)
0.0297 (7)
0.0347 (8)
0.0331 (8)
0.0282 (7)
0.0416 (9)
0.0336 (6)
0.0297 (5)
0.0276 (6)
0.0288 (5)
0.0247 (6)
0.0205 (7)
0.0214 (7)
0.0248 (7)
0.0285 (8)
0.0349 (8)
0.0236 (7)
0.0202 (7)
0.0204 (7)
0.0223 (7)
0.0172 (6)
0.0216 (7)
0.0241 (7)
0.0313 (8)
0.0278 (8)
0.0365 (9)
0.0013 (5)
0.0212 (4)
0.0274 (5)
0.0041 (4)
0.0042 (5)
0.0071 (5)
0.0040 (5)
0.0118 (6)
0.0097 (6)
0.0062 (6)
0.0064 (5)
0.0085 (5)
0.0046 (5)
0.0074 (5)
0.0065 (5)
0.0143 (6)
0.0174 (6)
0.0095 (6)
0.0060 (6)
0.0113 (7)
0.0032 (4)
0.0179 (4)
0.0234 (5)
0.0088 (4)
0.0033 (5)
0.0046 (5)
0.0043 (5)
0.0040 (5)
−0.0027 (5)
0.0019 (6)
0.0058 (5)
0.0013 (5)
0.0043 (5)
0.0057 (5)
0.0025 (5)
0.0089 (6)
−0.0023 (6)
−0.0005 (6)
0.0040 (6)
0.0199 (7)
0.0261 (5)
0.0142 (4)
0.0153 (4)
0.0113 (4)
0.0102 (5)
0.0031 (5)
0.0069 (5)
0.0084 (5)
0.0068 (5)
0.0084 (6)
0.0073 (5)
0.0018 (5)
0.0015 (5)
0.0010 (5)
0.0058 (5)
0.0073 (5)
0.0055 (6)
0.0037 (6)
0.0083 (6)
0.0147 (7)
C2
C3
C4
C5
C6
C11
C12
C21
C22
C31
C41
C51
C61
C211
Geometric parameters (Å, º)
O12—C12
O21—C22
O22—C22
O22—H22
O211—C211
O211—C21
N11—C11
N11—C12
N11—H11
C1—C12
C1—C6
1.2188 (17)
C31—C41
1.387 (2)
1.2180 (15)
1.3202 (15)
0.94 (2)
C41—C51
C51—C61
C1—H1
1.375 (2)
1.3926 (19)
0.9800
0.9800
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9300
0.9300
0.9300
0.9300
0.9600
0.9600
0.9600
1.4255 (18)
1.3705 (16)
1.4138 (16)
1.3520 (16)
0.867 (15)
1.5278 (17)
1.5355 (18)
1.5370 (16)
1.5413 (18)
1.5117 (17)
1.5197 (19)
1.5206 (18)
1.5319 (19)
1.3881 (19)
1.4021 (17)
1.3842 (18)
C2—H2
C3—H3A
C3—H3B
C4—H4A
C4—H4B
C5—H5A
C5—H5B
C6—H6A
C6—H6B
C31—H31
C41—H41
C51—H51
C61—H61
C211—H21A
C211—H21B
C211—H21C
C1—C2
C2—C3
C2—C22
C3—C4
C4—C5
C5—C6
C11—C61
C11—C21
C21—C31
C22—O22—H22
106.5 (13)
C22—C2—H2
107.00
Acta Cryst. (2012). C68, o327–o331
sup-3

supplementary materials
C21—O211—C211
C11—N11—C12
C12—N11—H11
C11—N11—H11
C2—C1—C6
117.55 (10)
128.84 (12)
119.8 (10)
111.3 (10)
112.86 (10)
109.56 (10)
116.96 (10)
110.70 (10)
112.47 (10)
111.18 (10)
111.44 (10)
111.35 (11)
112.20 (11)
111.51 (11)
116.06 (11)
119.37 (11)
124.56 (11)
116.37 (11)
120.40 (11)
123.19 (12)
114.89 (11)
124.91 (12)
120.20 (12)
112.97 (10)
122.14 (12)
124.89 (11)
119.62 (12)
120.77 (13)
119.94 (13)
120.10 (12)
106.00
C2—C3—H3A
C2—C3—H3B
C4—C3—H3A
C4—C3—H3B
H3A—C3—H3B
C3—C4—H4A
C3—C4—H4B
C5—C4—H4A
C5—C4—H4B
H4A—C4—H4B
C4—C5—H5A
C4—C5—H5B
C6—C5—H5A
C6—C5—H5B
H5A—C5—H5B
C1—C6—H6A
C1—C6—H6B
C5—C6—H6A
C5—C6—H6B
H6A—C6—H6B
C21—C31—H31
C41—C31—H31
C31—C41—H41
C51—C41—H41
C41—C51—H51
C61—C51—H51
C11—C61—H61
C51—C61—H61
109.00
109.00
109.00
109.00
108.00
109.00
109.00
109.00
109.00
108.00
109.00
109.00
109.00
109.00
108.00
109.00
109.00
109.00
109.00
108.00
120.00
120.00
120.00
120.00
120.00
120.00
120.00
120.00
C2—C1—C12
C6—C1—C12
C1—C2—C3
C1—C2—C22
C3—C2—C22
C2—C3—C4
C3—C4—C5
C4—C5—C6
C1—C6—C5
N11—C11—C21
C21—C11—C61
N11—C11—C61
N11—C12—C1
O12—C12—C1
O12—C12—N11
O211—C21—C11
O211—C21—C31
C11—C21—C31
O22—C22—C2
O21—C22—O22
O21—C22—C2
C21—C31—C41
C31—C41—C51
C41—C51—C61
C11—C61—C51
C2—C1—H1
O211—C211—H21A
O211—C211—H21B
O211—C211—H21C
H21A—C211—H21B
H21A—C211—H21C
H21B—C211—H21C
110.00
109.00
109.00
109.00
109.00
109.00
C6—C1—H1
105.00
C12—C1—H1
C1—C2—H2
105.00
107.00
C3—C2—H2
107.00
C211—O211—C21—C11
C211—O211—C21—C31
C12—N11—C11—C21
C12—N11—C11—C61
C11—N11—C12—O12
C11—N11—C12—C1
C6—C1—C2—C3
173.23 (11)
−7.53 (18)
175.18 (12)
−4.3 (2)
C1—C2—C22—O21
C1—C2—C22—O22
C3—C2—C22—O21
C3—C2—C22—O22
C2—C3—C4—C5
−6.84 (17)
173.17 (10)
117.95 (13)
−62.04 (14)
−56.81 (14)
55.64 (15)
−52.67 (14)
0.97 (16)
1.7 (2)
179.56 (11)
−52.76 (13)
72.30 (13)
175.02 (10)
−59.92 (13)
51.65 (14)
−179.88 (10)
−31.79 (16)
C3—C4—C5—C6
C4—C5—C6—C1
C6—C1—C2—C22
C12—C1—C2—C3
C12—C1—C2—C22
C2—C1—C6—C5
N11—C11—C21—O211
N11—C11—C21—C31
C61—C11—C21—O211
C61—C11—C21—C31
N11—C11—C61—C51
C21—C11—C61—C51
−178.31 (11)
−179.48 (11)
1.24 (19)
C12—C1—C6—C5
C2—C1—C12—O12
178.56 (12)
−0.95 (19)
Acta Cryst. (2012). C68, o327–o331
sup-4

supplementary materials
C2—C1—C12—N11
C6—C1—C12—O12
C6—C1—C12—N11
C1—C2—C3—C4
C22—C2—C3—C4
150.33 (11)
−161.82 (12)
20.30 (16)
O211—C21—C31—C41
−179.81 (12)
−0.61 (19)
−0.3 (2)
C11—C21—C31—C41
C21—C31—C41—C51
C31—C41—C51—C61
C41—C51—C61—C11
55.06 (13)
−70.72 (13)
0.6 (2)
0.0 (2)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N11—H11···O211
O22—H22···O21i
C3—H3A···O22
C6—H6B···O21
C51—H51···O12ii
C61—H61···O12
0.867 (15)
0.94 (2)
0.97
2.119 (15)
1.76 (2)
2.58
2.6003 (14)
2.6866 (14)
2.9294 (17)
3.1171 (16)
3.4232 (18)
2.8812 (17)
114.4 (12)
173 (2)
101
0.97
2.56
117
0.93
2.55
157
0.93
2.29
121
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y, −z.
(II) 2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
Crystal data
C15H17NO3
Mr = 259.30
F(000) = 552
Dx = 1.352 Mg m−3
Melting point: 428 K
Monoclinic, P21/n
Hall symbol: -P 2yn
a = 11.7119 (5) Å
b = 6.6705 (3) Å
c = 17.2898 (8) Å
β = 109.482 (5)°
V = 1273.42 (11) Å3
Z = 4
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4720 reflections
θ = 3.3–28.7°
µ = 0.09 mm−1
T = 200 K
Flat prism, purple brown
0.40 × 0.25 × 0.12 mm
Data collection
Oxford Diffraction Gemini-S CCD-detector
diffractometer
Radiation source: Enhance (Mo) X-ray source
Graphite monochromator
8552 measured reflections
2498 independent reflections
1959 reflections with I > 2σ(I)
Rint = 0.024
ω scans
θmax = 26.0°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
h = −14→14
k = −8→8
T
min = 0.929, Tmax = 0.981
l = −21→21
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.035
wR(F2) = 0.088
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.09
2498 reflections
172 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0496P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.17 e Å−3
Acta Cryst. (2012). C68, o327–o331
sup-5

supplementary materials
Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are
estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the
estimation of distances, angles and torsion angles
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O1
0.60601 (9)
0.44297 (8)
0.69783 (9)
0.54233 (9)
0.55873 (11)
0.48336 (11)
0.38378 (12)
0.26841 (12)
0.29309 (12)
0.37770 (12)
0.49925 (11)
0.48592 (12)
0.58123 (11)
0.54235 (11)
0.57910 (11)
0.65478 (11)
0.64175 (13)
0.69393 (12)
0.65808 (11)
0.36650
0.55074 (13)
0.03988 (12)
0.65459 (13)
0.31061 (14)
0.39094 (19)
0.12526 (17)
−0.08664 (18)
0.02011 (19)
0.18467 (19)
0.34107 (19)
0.25028 (18)
0.05478 (17)
0.40478 (18)
0.59554 (18)
0.68403 (18)
0.58023 (18)
0.8314 (2)
0.38858 (18)
0.30128 (18)
−0.17640
0.38265 (6)
0.20453 (5)
0.03909 (6)
0.28078 (6)
0.35851 (8)
0.26984 (8)
0.35410 (8)
0.35074 (9)
0.41557 (9)
0.40050 (8)
0.40214 (8)
0.35351 (7)
0.21881 (7)
0.19122 (8)
0.13073 (8)
0.09807 (8)
−0.00325 (9)
0.12627 (8)
0.18673 (8)
0.30750
0.0389 (3)
0.0335 (3)
0.0371 (3)
0.0248 (3)
0.0274 (4)
0.0243 (4)
0.0307 (4)
0.0337 (4)
0.0343 (5)
0.0316 (4)
0.0270 (4)
0.0263 (4)
0.0243 (4)
0.0270 (4)
0.0283 (4)
0.0266 (4)
0.0400 (5)
0.0293 (4)
0.0272 (4)
0.0370*
O3
O41
N2
C1
C3
C4
C5
C6
C7
C8
C9
C11
C21
C31
C41
C42
C51
C61
H4A
H4B
H5A
H5B
H6A
H6B
H7A
H7B
H8
0.41090
−0.16770
0.40350
0.0370*
0.21180
−0.07600
0.35960
0.0400*
0.23160
0.07860
0.29680
0.0400*
0.21740
0.24750
0.41350
0.0410*
0.32960
0.12670
0.46970
0.0410*
0.39280
0.44440
0.44220
0.0380*
0.33870
0.40360
0.34760
0.0380*
0.55210
0.22960
0.45890
0.0320*
H9
0.56180
−0.01950
0.37740
0.0320*
H21
H31
H42A
H42B
H42C
H51
H61
0.49140
0.66480
0.21320
0.0320*
0.55300
0.81250
0.11220
0.0340*
0.65590
0.94100
0.03480
0.0480*
0.55620
0.80940
−0.02760
−0.04540
0.10420
0.0480*
0.67550
0.86260
0.0480*
0.74460
0.31890
0.0350*
0.68520
0.17370
0.20590
0.0330*
Acta Cryst. (2012). C68, o327–o331
sup-6

supplementary materials
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
0.0453 (6)
0.0460 (6)
0.0447 (6)
0.0272 (6)
0.0250 (7)
0.0247 (7)
0.0418 (8)
0.0316 (7)
0.0355 (8)
0.0394 (8)
0.0307 (7)
0.0279 (7)
0.0237 (7)
0.0253 (7)
0.0296 (7)
0.0258 (7)
0.0452 (9)
0.0272 (7)
0.0244 (7)
0.0348 (5)
0.0277 (5)
0.0356 (5)
0.0238 (5)
0.0285 (7)
0.0206 (6)
0.0227 (7)
0.0332 (7)
0.0366 (8)
0.0256 (7)
0.0288 (7)
0.0238 (6)
0.0255 (6)
0.0265 (7)
0.0234 (6)
0.0282 (7)
0.0434 (8)
0.0283 (7)
0.0235 (6)
0.0367 (6)
0.0285 (5)
0.0411 (6)
0.0252 (6)
0.0269 (7)
0.0289 (7)
0.0291 (7)
0.0373 (8)
0.0359 (8)
0.0329 (7)
0.0200 (6)
0.0269 (7)
0.0246 (6)
0.0326 (7)
0.0331 (7)
0.0276 (7)
0.0342 (8)
0.0372 (8)
0.0339 (7)
−0.0172 (5)
−0.0054 (4)
0.0045 (4)
−0.0029 (4)
−0.0027 (5)
0.0032 (5)
−0.0045 (6)
−0.0089 (6)
−0.0021 (6)
−0.0014 (6)
−0.0048 (5)
0.0024 (5)
−0.0025 (5)
0.0026 (5)
0.0044 (5)
−0.0022 (5)
0.0015 (7)
0.0036 (5)
0.0032 (5)
0.0137 (5)
0.0147 (4)
0.0279 (5)
0.0112 (4)
0.0063 (5)
0.0105 (5)
0.0138 (6)
0.0127 (6)
0.0187 (6)
0.0161 (6)
0.0066 (5)
0.0089 (5)
0.0093 (5)
0.0143 (6)
0.0122 (6)
0.0112 (5)
0.0168 (7)
0.0171 (6)
0.0100 (6)
−0.0077 (4)
−0.0053 (4)
0.0094 (4)
0.0004 (4)
−0.0008 (6)
0.0006 (5)
0.0022 (6)
0.0009 (6)
0.0003 (6)
−0.0032 (6)
−0.0001 (5)
0.0046 (5)
0.0004 (5)
−0.0007 (6)
0.0049 (6)
0.0010 (5)
0.0125 (7)
−0.0005 (6)
0.0038 (5)
O3
O41
N2
C1
C3
C4
C5
C6
C7
C8
C9
C11
C21
C31
C41
C42
C51
C61
Geometric parameters (Å, º)
O1—C1
O3—C3
O41—C41
O41—C42
N2—C1
N2—C3
N2—C11
C1—C8
1.2095 (16)
C41—C51
1.3904 (17)
1.2112 (15)
1.3723 (17)
1.4274 (17)
1.3993 (16)
1.3980 (15)
1.4408 (16)
1.5117 (18)
1.5119 (17)
1.511 (2)
C51—C61
C4—H4A
C4—H4B
C5—H5A
C5—H5B
C6—H6A
C6—H6B
C7—H7A
C7—H7B
C8—H8
1.3787 (19)
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9800
0.9800
0.9300
0.9300
0.9600
0.9600
0.9600
0.9300
0.9300
C3—C9
C4—C5
C4—C9
1.5262 (19)
1.5260 (19)
1.520 (2)
C5—C6
C9—H9
C6—C7
C21—H21
C31—H31
C42—H42A
C42—H42B
C42—H42C
C51—H51
C61—H61
C7—C8
1.539 (2)
C8—C9
1.5311 (17)
1.3817 (17)
1.3883 (18)
1.3884 (18)
1.3848 (19)
C11—C21
C11—C61
C21—C31
C31—C41
C41—O41—C42
C1—N2—C3
C1—N2—C11
C3—N2—C11
O1—C1—N2
117.36 (11)
111.84 (10)
124.83 (10)
123.33 (10)
124.70 (12)
C4—C5—H5A
C4—C5—H5B
C6—C5—H5A
C6—C5—H5B
H5A—C5—H5B
109.00
109.00
109.00
109.00
108.00
Acta Cryst. (2012). C68, o327–o331
sup-7

supplementary materials
O1—C1—C8
127.51 (12)
107.64 (10)
124.32 (12)
128.52 (11)
107.12 (10)
113.66 (10)
111.27 (12)
110.02 (12)
112.26 (11)
108.91 (10)
103.54 (10)
113.63 (11)
115.67 (10)
103.09 (9)
117.35 (11)
120.58 (11)
119.23 (11)
120.20 (12)
120.15 (12)
119.73 (11)
124.48 (11)
115.66 (12)
119.85 (12)
120.40 (13)
119.66 (11)
109.00
C5—C6—H6A
C5—C6—H6B
C7—C6—H6A
C7—C6—H6B
H6A—C6—H6B
C6—C7—H7A
C6—C7—H7B
C8—C7—H7A
C8—C7—H7B
H7A—C7—H7B
C1—C8—H8
110.00
110.00
110.00
110.00
108.00
109.00
109.00
109.00
109.00
108.00
110.00
110.00
110.00
107.00
107.00
107.00
120.00
120.00
120.00
120.00
109.00
109.00
109.00
N2—C1—C8
O3—C3—N2
O3—C3—C9
N2—C3—C9
C5—C4—C9
C4—C5—C6
C5—C6—C7
C6—C7—C8
C1—C8—C7
C1—C8—C9
C7—C8—C9
C7—C8—H8
C3—C9—C4
C9—C8—H8
C3—C9—C8
C3—C9—H9
C4—C9—C8
C4—C9—H9
N2—C11—C21
N2—C11—C61
C21—C11—C61
C11—C21—C31
C21—C31—C41
O41—C41—C31
O41—C41—C51
C31—C41—C51
C41—C51—C61
C11—C61—C51
C5—C4—H4A
C5—C4—H4B
C9—C4—H4A
C9—C4—H4B
H4A—C4—H4B
C8—C9—H9
C11—C21—H21
C31—C21—H21
C21—C31—H31
C41—C31—H31
O41—C42—H42A
O41—C42—H42B
O41—C42—H42C
H42A—C42—H42B
H42A—C42—H42C
H42B—C42—H42C
C41—C51—H51
C61—C51—H51
C11—C61—H61
C51—C61—H61
109.00
110.00
110.00
120.00
120.00
120.00
120.00
109.00
109.00
109.00
108.00
C42—O41—C41—C31
C42—O41—C41—C51
C3—N2—C1—C8
C11—N2—C1—C8
C11—N2—C3—C9
C1—N2—C11—C21
C3—N2—C11—C21
C3—N2—C1—O1
C11—N2—C1—O1
C11—N2—C3—O3
C1—N2—C3—C9
C1—N2—C11—C61
C3—N2—C11—C61
C1—N2—C3—O3
N2—C1—C8—C7
O1—C1—C8—C9
N2—C1—C8—C9
O1—C1—C8—C7
−13.59 (19)
167.66 (12)
−3.10 (14)
177.11 (11)
166.12 (11)
−56.72 (18)
123.52 (13)
−179.06 (13)
1.2 (2)
C5—C4—C9—C8
C5—C4—C9—C3
C9—C4—C5—C6
C4—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C1
C6—C7—C8—C9
C7—C8—C9—C3
C7—C8—C9—C4
C1—C8—C9—C3
C1—C8—C9—C4
N2—C11—C61—C51
C21—C11—C61—C51
N2—C11—C21—C31
C61—C11—C21—C31
C11—C21—C31—C41
C21—C31—C41—C51
C21—C31—C41—O41
38.31 (15)
−83.79 (14)
−50.57 (15)
61.34 (14)
−58.69 (15)
160.25 (11)
45.42 (15)
92.97 (13)
−35.41 (15)
−25.01 (13)
−153.39 (11)
178.75 (12)
−1.00 (19)
−179.18 (12)
0.57 (19)
−11.6 (2)
−13.68 (14)
123.53 (13)
−56.23 (17)
168.63 (13)
−103.15 (12)
−166.11 (14)
18.08 (13)
72.67 (17)
0.08 (19)
−0.3 (2)
−179.00 (12)
Acta Cryst. (2012). C68, o327–o331
sup-8

supplementary materials
O3—C3—C9—C8
N2—C3—C9—C4
O3—C3—C9—C4
N2—C3—C9—C8
−158.30 (14)
153.56 (11)
−28.9 (2)
O41—C41—C51—C61
178.67 (12)
−0.1 (2)
0.8 (2)
C31—C41—C51—C61
C41—C51—C61—C11
24.14 (14)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C21—H21···O3i
C51—H51···O1ii
0.93
0.93
2.56
2.46
3.2205 (15)
3.2914 (17)
128
149
Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y−1/2, −z+1/2.
(III) cis-3-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid
Crystal data
C15H15NO4
Mr = 273.28
F(000) = 576
Dx = 1.383 Mg m−3
Orthorhombic, P212121
Hall symbol: P 2ac 2ab
a = 6.4958 (2) Å
b = 12.5236 (4) Å
c = 16.1281 (6) Å
V = 1312.03 (8) Å3
Z = 4
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2474 reflections
θ = 3.3–28.7°
µ = 0.10 mm−1
T = 200 K
Needles, colourless
0.45 × 0.12 × 0.08 mm
Data collection
Oxford Diffraction Gemini-S Ultra CCD-
detector
diffractometer
Radiation source: Enhance (Mo) X-ray source
Graphite monochromator
Detector resolution: 16.077 pixels mm-1
ω scans
Tmin = 0.980, Tmax = 0.990
4693 measured reflections
1728 independent reflections
1395 reflections with I > 2σ(I)
Rint = 0.024
θmax = 28.0°, θmin = 3.3°
h = −8→8
k = −16→12
l = −21→9
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.038
wR(F2) = 0.086
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.10
1728 reflections
185 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0446P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.18 e Å−3
Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are
estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the
estimation of distances, angles and torsion angles
Acta Cryst. (2012). C68, o327–o331
sup-9

supplementary materials
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O1
0.3742 (2)
−0.0620 (3)
0.3658 (3)
0.1156 (3)
0.1305 (3)
0.2977 (3)
0.0710 (4)
0.0431 (4)
0.1575 (4)
0.3037 (4)
0.4642 (4)
0.3732 (4)
0.1892 (4)
0.0356 (3)
0.1500 (3)
0.0592 (3)
−0.1440 (3)
−0.2570 (3)
−0.1674 (3)
0.1794 (3)
−0.04230
−0.04680
0.23510
0.03578 (12)
0.20661 (15)
0.40076 (13)
0.41628 (12)
0.12973 (13)
0.06243 (16)
0.14497 (18)
−0.0268 (2)
−0.1282 (2)
−0.15842 (19)
−0.07326 (19)
0.03688 (18)
0.06670 (18)
0.18358 (16)
0.25567 (16)
0.30532 (17)
0.28329 (18)
0.21244 (19)
0.16229 (17)
0.37990 (17)
−0.03990
0.64532 (10)
0.46989 (11)
0.77921 (11)
0.87409 (10)
0.57271 (11)
0.57948 (15)
0.49016 (15)
0.41929 (17)
0.39722 (17)
0.46748 (18)
0.47977 (17)
0.49230 (15)
0.43767 (15)
0.64192 (14)
0.68784 (13)
0.75634 (13)
0.77614 (15)
0.72850 (15)
0.66081 (15)
0.80984 (15)
0.46760
0.0283 (5)
0.0471 (7)
0.0336 (6)
0.0306 (5)
0.0190 (5)
0.0203 (7)
0.0267 (7)
0.0337 (8)
0.0394 (9)
0.0407 (9)
0.0352 (8)
0.0273 (7)
0.0281 (8)
0.0176 (6)
0.0190 (6)
0.0201 (6)
0.0248 (7)
0.0280 (7)
0.0235 (7)
0.0216 (7)
0.0400*
O3
O31
O32
N2
C1
C3
C4
C5
C6
C7
C8
C9
C11
C21
C31
C41
C51
C61
C311
H4A
H4B
H5A
H5B
H6A
H6B
H7A
H7B
H8
−0.00740
0.37370
0.0400*
−0.11750
0.34650
0.0470*
0.06000
−0.18560
0.38800
0.0470*
0.22610
−0.16770
0.51830
0.0490*
0.37050
−0.22570
0.45450
0.0490*
0.55400
−0.07180
0.43170
0.0420*
0.54740
−0.09140
0.52770
0.0420*
0.48270
0.08820
0.47970
0.0330*
H9
0.23550
0.10040
0.38610
0.0340*
H21
H31
H41
H51
H61
0.28550
0.27090
0.67330
0.0230*
0.427 (4)
−0.20480
−0.39360
−0.24330
0.444 (2)
0.8157 (19)
0.82170
0.049 (9)*
0.0300*
0.31630
0.19840
0.74190
0.0340*
0.11490
0.62860
0.0280*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
0.0247 (9)
0.0641 (13)
0.0260 (9)
0.0310 (8)
0.0292 (9)
0.0293 (10)
0.0332 (10)
0.0063 (8)
0.0328 (11)
−0.0113 (9)
−0.0091 (8)
−0.0152 (10)
0.0027 (8)
0.0012 (7)
−0.0065 (9)
−0.0162 (8)
O3
0.0478 (11)
0.0416 (10)
O31
Acta Cryst. (2012). C68, o327–o331
sup-10

supplementary materials
O32
N2
0.0373 (10)
0.0194 (9)
0.0321 (8)
0.0179 (8)
0.0225 (9)
−0.0037 (8)
0.0011 (8)
0.0027 (8)
−0.0083 (8)
−0.0012 (7)
−0.0014 (10)
−0.0011 (10)
−0.0062 (12)
−0.0127 (12)
−0.0073 (12)
−0.0102 (12)
−0.0064 (10)
−0.0008 (10)
0.0007 (9)
0.0197 (10)
0.0303 (13)
0.0215 (12)
0.0294 (14)
0.0344 (15)
0.0429 (17)
0.0367 (15)
0.0279 (13)
0.0215 (13)
0.0188 (11)
0.0198 (11)
0.0188 (11)
0.0223 (11)
0.0326 (14)
0.0292 (13)
0.0223 (12)
−0.0033 (8)
−0.0039 (10)
−0.0058 (11)
−0.0093 (13)
−0.0098 (14)
−0.0094 (15)
−0.0038 (12)
0.0001 (12)
0.0007 (11)
−0.0038 (10)
−0.0014 (10)
−0.0023 (10)
0.0035 (11)
0.0019 (11)
−0.0051 (10)
−0.0018 (10)
C1
0.0166 (11)
0.0352 (14)
0.0342 (14)
0.0484 (17)
0.0509 (18)
0.0299 (14)
0.0242 (12)
0.0358 (14)
0.0181 (11)
0.0169 (11)
0.0216 (11)
0.0229 (12)
0.0169 (11)
0.0194 (12)
0.0223 (12)
0.0141 (10)
0.0235 (11)
0.0375 (14)
0.0354 (13)
0.0283 (13)
0.0391 (14)
0.0299 (12)
0.0271 (12)
0.0158 (10)
0.0203 (10)
0.0198 (10)
0.0293 (11)
0.0346 (13)
0.0218 (11)
0.0202 (11)
−0.0029 (9)
0.0037 (11)
0.0048 (13)
0.0015 (14)
0.0087 (13)
0.0108 (13)
−0.0015 (11)
0.0061 (11)
0.0030 (9)
C3
C4
C5
C6
C7
C8
C9
C11
C21
C31
C41
C51
C61
C311
−0.0011 (10)
0.0009 (10)
0.0034 (11)
−0.0040 (11)
−0.0035 (10)
0.0026 (10)
0.0013 (9)
0.0024 (9)
−0.0024 (10)
0.0029 (12)
−0.0010 (10)
0.0016 (9)
Geometric parameters (Å, º)
O1—C1
1.219 (3)
C31—C41
1.386 (3)
O3—C3
1.204 (3)
1.334 (3)
1.206 (3)
0.89 (3)
C31—C311
C41—C51
C51—C61
C4—H4A
C4—H4B
C5—H5A
C5—H5B
C6—H6A
C6—H6B
C7—H7A
C7—H7B
C8—H8
1.492 (3)
1.384 (3)
1.388 (3)
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9800
0.9800
0.9300
0.9300
0.9300
0.9300
O31—C311
O32—C311
O31—H31
N2—C3
1.399 (3)
1.443 (3)
1.379 (3)
1.523 (3)
1.506 (3)
1.536 (4)
1.514 (4)
1.526 (4)
1.505 (4)
1.514 (3)
1.531 (4)
1.379 (3)
1.384 (3)
1.398 (3)
N2—C11
N2—C1
C1—C8
C3—C9
C4—C9
C4—C5
C5—C6
C6—C7
C9—H9
C7—C8
C21—H21
C41—H41
C51—H51
C61—H61
C8—C9
C11—C61
C11—C21
C21—C31
C311—O31—H31
C1—N2—C3
C3—N2—C11
C1—N2—C11
O1—C1—C8
N2—C1—C8
O1—C1—N2
O3—C3—N2
N2—C3—C9
O3—C3—C9
106.2 (18)
C9—C4—H4A
C4—C5—H5A
C4—C5—H5B
C6—C5—H5A
C6—C5—H5B
H5A—C5—H5B
C7—C6—H6A
C7—C6—H6B
C5—C6—H6B
C5—C6—H6A
109.00
110.00
110.00
110.00
110.00
108.00
110.00
110.00
109.00
110.00
112.10 (19)
123.67 (18)
124.13 (18)
127.98 (19)
107.99 (19)
123.9 (2)
123.0 (2)
107.78 (19)
129.1 (2)
Acta Cryst. (2012). C68, o327–o331
sup-11

supplementary materials
C5—C4—C9
112.4 (2)
109.8 (2)
110.7 (2)
113.1 (2)
116.1 (2)
116.8 (2)
103.22 (19)
106.8 (2)
114.04 (19)
103.49 (19)
119.28 (19)
121.4 (2)
119.31 (18)
119.10 (18)
119.69 (19)
120.97 (18)
119.33 (19)
120.3 (2)
120.29 (19)
119.2 (2)
108.00
H6A—C6—H6B
H7A—C7—H7B
C6—C7—H7B
C8—C7—H7B
C6—C7—H7A
C8—C7—H7A
C1—C8—H8
108.00
108.00
109.00
109.00
109.00
109.00
107.00
107.00
107.00
111.00
C4—C5—C6
C5—C6—C7
C6—C7—C8
C1—C8—C7
C7—C8—C9
C1—C8—C9
C3—C9—C4
C7—C8—H8
C4—C9—C8
C9—C8—H8
C3—C9—C8
C3—C9—H9
N2—C11—C61
C21—C11—C61
N2—C11—C21
C11—C21—C31
C21—C31—C41
C21—C31—C311
C41—C31—C311
C31—C41—C51
C41—C51—C61
C11—C61—C51
H4A—C4—H4B
C5—C4—H4B
C9—C4—H4B
C5—C4—H4A
C8—C9—H9
111.00
C4—C9—H9
111.00
C11—C21—H21
C31—C21—H21
C51—C41—H41
C31—C41—H41
C41—C51—H51
C61—C51—H51
C11—C61—H61
C51—C61—H61
O31—C311—C31
O32—C311—C31
O31—C311—O32
120.00
120.00
120.00
120.00
120.00
120.00
120.00
120.00
112.55 (19)
123.63 (19)
123.8 (2)
109.00
109.00
109.00
C3—N2—C1—O1
C3—N2—C1—C8
C11—N2—C1—O1
C11—N2—C1—C8
C1—N2—C3—O3
C1—N2—C3—C9
C11—N2—C3—O3
C11—N2—C3—C9
C1—N2—C11—C21
C1—N2—C11—C61
C3—N2—C11—C21
C3—N2—C11—C61
O1—C1—C8—C7
O1—C1—C8—C9
N2—C1—C8—C7
N2—C1—C8—C9
O3—C3—C9—C4
O3—C3—C9—C8
N2—C3—C9—C4
N2—C3—C9—C8
C9—C4—C5—C6
C5—C4—C9—C3
C5—C4—C9—C8
−178.5 (2)
5.7 (2)
C4—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C1
C6—C7—C8—C9
C1—C8—C9—C3
C1—C8—C9—C4
C7—C8—C9—C3
C7—C8—C9—C4
−62.6 (3)
53.8 (3)
81.3 (3)
−40.9 (3)
22.7 (2)
−93.0 (2)
151.4 (2)
35.7 (3)
5.1 (3)
−170.65 (18)
−174.6 (2)
9.7 (3)
1.8 (4)
−173.96 (19)
61.8 (3)
N2—C11—C21—C31
C61—C11—C21—C31
N2—C11—C61—C51
C21—C11—C61—C51
C11—C21—C31—C41
C11—C21—C31—C311
C21—C31—C41—C51
C311—C31—C41—C51
C21—C31—C311—O31
C21—C31—C311—O32
C41—C31—C311—O31
C41—C31—C311—O32
C31—C41—C51—C61
C41—C51—C61—C11
−178.14 (18)
2.0 (3)
−118.4 (2)
−114.2 (2)
65.7 (3)
178.6 (2)
−1.5 (3)
−1.2 (3)
177.28 (19)
0.1 (3)
37.3 (3)
166.3 (2)
−147.2 (2)
−18.1 (2)
−75.2 (3)
164.1 (3)
100.2 (2)
−20.5 (2)
57.4 (3)
−178.5 (2)
7.1 (3)
−172.2 (2)
−174.4 (2)
6.3 (3)
0.4 (3)
−157.6 (2)
−43.9 (3)
0.3 (3)
Acta Cryst. (2012). C68, o327–o331
sup-12

supplementary materials
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
O31—H31···O1i
C21—H21···O3ii
0.89 (3)
0.93
1.84 (3)
2.53
2.682 (2)
3.193 (3)
156 (3)
129
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1.
(IV) rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol- 2-yl)benzoic acid monohydrate
Crystal data
C15H15NO4·H2O
Mr = 291.30
F(000) = 616
Dx = 1.363 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2417 reflections
θ = 3.1–28.7°
Monoclinic, P21/n
Hall symbol: -P 2yn
a = 13.077 (2) Å
b = 6.6713 (7) Å
c = 16.432 (2) Å
β = 97.982 (13)°
V = 1419.6 (3) Å3
Z = 4
µ = 0.10 mm−1
T = 200 K
Prism, colourless
0.30 × 0.10 × 0.08 mm
Data collection
Oxford Diffraction Gemini-S CCD-detector
diffractometer
Radiation source: Enhance (Mo) X-ray source
Graphite monochromator
Detector resolution: 16.077 pixels mm-1
ω scans
9649 measured reflections
2790 independent reflections
1374 reflections with I > 2σ(I)
Rint = 0.055
θmax = 26.0°, θmin = 3.2°
h = −16→13
k = −8→8
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
l = −14→20
T
min = 0.813, Tmax = 0.980
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.052
wR(F2) = 0.132
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 0.85
2790 reflections
194 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0704P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.34 e Å−3
Δρmin = −0.20 e Å−3
Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are
estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the
estimation of distances, angles and torsion angles
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is
used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Acta Cryst. (2012). C68, o327–o331
sup-13

supplementary materials
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
Occ. (<1)
O1
0.80344 (15)
0.58298 (15)
0.50408 (17)
0.53908 (18)
0.68963 (16)
0.7620 (2)
0.6525 (2)
0.6735 (3)
0.6294 (3)
0.7017 (3)
0.7239 (3)
0.7723 (2)
0.7219 (2)
0.65230 (19)
0.6115 (2)
0.5750 (2)
0.57975 (19)
0.6220 (2)
0.6595 (2)
0.5398 (2)
0.9383 (2)
0.9381 (10)
0.61920
0.0890 (3)
0.6120 (2)
−0.2147 (3)
0.0528 (3)
0.3350 (3)
0.2489 (4)
0.5193 (3)
0.7105 (4)
0.5965 (5)
0.4390 (4)
0.2867 (4)
0.3861 (4)
0.5812 (4)
0.2395 (3)
0.0499 (3)
−0.0399 (4)
0.0608 (4)
0.2516 (4)
0.3428 (4)
−0.0315 (4)
−0.1718 (3)
0.0061 (18)
0.79100
0.54274 (11)
0.56137 (11)
0.82985 (12)
0.90848 (13)
0.57093 (12)
0.52623 (16)
0.53794 (15)
0.40365 (19)
0.3295 (2)
0.30655 (18)
0.37592 (16)
0.45460 (15)
0.47533 (17)
0.64028 (14)
0.63172 (15)
0.69778 (15)
0.77213 (15)
0.78004 (16)
0.71395 (15)
0.84418 (18)
0.46543 (15)
0.4139 (7)
0.42180
0.0502 (7)
0.0480 (7)
0.0632 (9)
0.0732 (10)
0.0333 (7)
0.0370 (9)
0.0371 (10)
0.0664 (14)
0.0707 (14)
0.0656 (13)
0.0580 (13)
0.0422 (10)
0.0490 (10)
0.0312 (8)
0.0361 (9)
0.0376 (9)
0.0341 (9)
0.0397 (9)
0.0370 (9)
0.0461 (11)
0.0644 (10)
0.079 (3)*
0.0800*
O3
O41
O42
N2
C1
C3
C4
C5
C6
C7
C8
C9
C11
C21
C31
C41
C51
C61
C411
O1W
O2W
H4A
H4B
H5A
H5B
H6A
H6B
H7A
H7B
H8
0.810
0.190
0.72560
0.80150
0.38870
0.0800*
0.61330
0.68870
0.28380
0.0850*
0.56550
0.53340
0.33950
0.0850*
0.76580
0.50090
0.29610
0.0790*
0.67120
0.37170
0.25670
0.0790*
0.66000
0.22200
0.38490
0.0690*
0.77020
0.18440
0.36030
0.0690*
0.84560
0.41010
0.45180
0.0510*
H9
0.77710
0.66240
0.50550
0.0590*
H21
H31
H41
H51
H61
H11W
H12W
H21W
H22W
0.60850
−0.01750
−0.16830
−0.25400
0.31920
0.58190
0.0430*
0.54720
0.69240
0.0450*
0.48190
0.87690
0.0950*
0.62530
0.82980
0.0480*
0.68860
0.47010
0.71910
0.0440*
0.89650
−0.09080
−0.26180
0.02910
0.47990
0.0970*
0.810
0.810
0.190
0.190
0.94650
0.49990
0.0970*
0.89720
0.45270
0.1180*
0.96620
0.12910
0.41170
0.1180*
Atomic displacement parameters (Å2)
U11
U22
0.0463 (11)
U33
U12
U13
U23
O1
0.0626 (14)
0.0474 (12)
0.0216 (10)
0.0273 (10)
0.0153 (9)
Acta Cryst. (2012). C68, o327–o331
sup-14

supplementary materials
O3
0.0564 (14)
0.0800 (17)
0.0885 (19)
0.0435 (15)
0.0432 (18)
0.0484 (19)
0.091 (3)
0.0348 (10)
0.0664 (14)
0.1014 (17)
0.0305 (11)
0.0394 (15)
0.0287 (14)
0.0535 (19)
0.071 (2)
0.0570 (13)
0.0488 (13)
0.0363 (13)
0.0289 (12)
0.0311 (15)
0.0355 (16)
0.059 (2)
0.0078 (9)
0.0228 (11)
0.0285 (12)
0.0319 (12)
0.0157 (11)
0.0148 (13)
0.0102 (14)
0.026 (2)
−0.0050 (9)
0.0104 (10)
−0.0105 (12)
−0.0005 (9)
0.0002 (12)
−0.0047 (11)
0.0202 (16)
0.0190 (18)
0.0000 (15)
−0.0030 (13)
0.0066 (12)
0.0070 (13)
−0.0015 (11)
−0.0035 (11)
−0.0014 (12)
0.0009 (12)
−0.0099 (12)
−0.0078 (13)
0.0037 (15)
0.0055 (13)
O41
O42
N2
−0.0164 (11)
−0.0290 (13)
0.0023 (9)
C1
0.0026 (13)
−0.0019 (12)
0.0228 (17)
0.0037 (18)
0.0043 (18)
−0.0029 (15)
0.0060 (12)
0.0025 (14)
0.0027 (11)
0.0016 (12)
−0.0031 (11)
0.0007 (11)
−0.0018 (13)
−0.0046 (11)
−0.0030 (14)
0.0183 (13)
C3
C4
C5
0.070 (3)
0.065 (2)
−0.012 (2)
−0.0004 (18)
0.0088 (18)
0.0150 (14)
0.0178 (15)
0.0120 (12)
0.0133 (13)
0.0102 (13)
0.0107 (12)
0.0104 (13)
0.0113 (13)
0.0136 (14)
0.0533 (15)
C6
0.093 (3)
0.063 (2)
0.0380 (18)
0.0397 (18)
0.0356 (16)
0.0426 (17)
0.0291 (14)
0.0299 (15)
0.0378 (16)
0.0312 (15)
0.0298 (15)
0.0402 (16)
0.0399 (18)
0.0693 (18)
C7
0.090 (3)
0.0442 (17)
0.0395 (15)
0.0412 (16)
0.0317 (13)
0.0348 (15)
0.0350 (14)
0.0423 (15)
0.0520 (16)
0.0390 (14)
0.061 (2)
C8
0.054 (2)
C9
0.066 (2)
C11
C21
C31
C41
C51
C61
C411
O1W
0.0349 (16)
0.0458 (18)
0.0413 (18)
0.0306 (16)
0.0389 (17)
0.0335 (16)
0.0396 (18)
0.078 (2)
0.0581 (14)
Geometric parameters (Å, º)
O1—C1
1.210 (3)
C11—C61
1.385 (3)
O3—C3
1.206 (3)
1.318 (3)
1.198 (4)
0.9000
C21—C31
C31—C41
C41—C411
C41—C51
C51—C61
C4—H4B
C4—H4A
C5—H5B
C5—H5A
C6—H6B
C6—H6A
C7—H7A
C7—H7B
C8—H8
1.382 (3)
1.388 (4)
1.492 (4)
1.387 (4)
1.392 (4)
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9700
0.9800
0.9800
0.9300
0.9300
0.9300
0.9300
O41—C411
O42—C411
O41—H41
O1W—H12W
O1W—H11W
O2W—H22W
O2W—H21W
N2—C1
0.8200
0.8300
0.9000
0.9000
1.399 (3)
1.403 (3)
1.448 (3)
1.512 (4)
1.521 (4)
1.483 (5)
1.525 (4)
1.496 (5)
1.525 (4)
1.512 (4)
1.519 (4)
1.372 (3)
N2—C3
N2—C11
C1—C8
C3—C9
C4—C5
C4—C9
C9—H9
C5—C6
C21—H21
C31—H31
C51—H51
C61—H61
C6—C7
C7—C8
C8—C9
C11—C21
C411—O41—H41
H11W—O1W—H12W
H21W—O2W—H22W
C1—N2—C3
105.00
108.00
99.00
C9—C4—H4A
C9—C4—H4B
C4—C5—H5B
C6—C5—H5A
H5A—C5—H5B
109.00
109.00
109.00
109.00
108.00
112.3 (2)
124.0 (2)
C1—N2—C11
Acta Cryst. (2012). C68, o327–o331
sup-15

supplementary materials
C3—N2—C11
N2—C1—C8
123.6 (2)
107.5 (2)
128.5 (2)
124.0 (2)
107.0 (2)
124.2 (2)
128.6 (2)
114.6 (2)
112.3 (3)
109.9 (3)
111.2 (2)
109.2 (2)
115.1 (2)
104.8 (2)
117.0 (2)
117.3 (2)
103.7 (2)
118.7 (2)
121.8 (2)
119.6 (2)
119.4 (2)
120.2 (2)
119.7 (2)
118.9 (2)
121.4 (2)
120.5 (2)
118.4 (2)
108.00
C4—C5—H5A
C6—C5—H5B
C5—C6—H6B
C7—C6—H6A
H6A—C6—H6B
C7—C6—H6B
C5—C6—H6A
C8—C7—H7B
C6—C7—H7A
C6—C7—H7B
C8—C7—H7A
H7A—C7—H7B
C7—C8—H8
109.00
109.00
110.00
110.00
108.00
110.00
110.00
109.00
109.00
109.00
109.00
108.00
109.00
109.00
109.00
106.00
106.00
106.00
120.00
120.00
120.00
120.00
120.00
120.00
121.00
121.00
123.6 (2)
123.2 (3)
113.3 (2)
O1—C1—C8
O1—C1—N2
N2—C3—C9
O3—C3—N2
O3—C3—C9
C5—C4—C9
C4—C5—C6
C5—C6—C7
C6—C7—C8
C1—C8—C7
C7—C8—C9
C1—C8—C9
C9—C8—H8
C3—C9—C4
C1—C8—H8
C4—C9—C8
C8—C9—H9
C3—C9—C8
C3—C9—H9
N2—C11—C61
C21—C11—C61
N2—C11—C21
C11—C21—C31
C21—C31—C41
C31—C41—C51
C51—C41—C411
C31—C41—C411
C41—C51—C61
C11—C61—C51
H4A—C4—H4B
C5—C4—H4A
C5—C4—H4B
C4—C9—H9
C11—C21—H21
C31—C21—H21
C21—C31—H31
C41—C31—H31
C41—C51—H51
C61—C51—H51
C11—C61—H61
C51—C61—H61
O42—C411—C41
O41—C411—O42
O41—C411—C41
109.00
109.00
C3—N2—C1—O1
C3—N2—C1—C8
C11—N2—C1—O1
C11—N2—C1—C8
C1—N2—C3—O3
C1—N2—C3—C9
C11—N2—C3—O3
C11—N2—C3—C9
C1—N2—C11—C21
C1—N2—C11—C61
C3—N2—C11—C21
C3—N2—C11—C61
O1—C1—C8—C7
O1—C1—C8—C9
N2—C1—C8—C7
N2—C1—C8—C9
O3—C3—C9—C4
O3—C3—C9—C8
−179.1 (2)
−1.8 (3)
C4—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C1
C6—C7—C8—C9
C1—C8—C9—C3
C1—C8—C9—C4
C7—C8—C9—C3
C7—C8—C9—C4
61.6 (4)
−59.7 (4)
162.2 (3)
44.7 (4)
−2.7 (4)
174.6 (2)
172.9 (2)
−11.9 (3)
−3.5 (4)
−20.8 (3)
−151.4 (2)
99.2 (3)
171.7 (2)
−53.8 (3)
125.9 (3)
122.2 (3)
−58.2 (3)
67.9 (4)
−31.4 (4)
N2—C11—C21—C31
C61—C11—C21—C31
N2—C11—C61—C51
C21—C11—C61—C51
C11—C21—C31—C41
C21—C31—C41—C51
C21—C31—C41—C411
C31—C41—C51—C61
C411—C41—C51—C61
C31—C41—C411—O41
−179.3 (2)
1.0 (4)
179.0 (2)
−1.4 (4)
−0.1 (4)
−0.5 (4)
179.3 (2)
0.1 (4)
−168.3 (3)
−109.3 (3)
14.6 (3)
−34.1 (4)
−164.9 (3)
−179.6 (2)
2.0 (4)
Acta Cryst. (2012). C68, o327–o331
sup-16

supplementary materials
N2—C3—C9—C4
N2—C3—C9—C8
C9—C4—C5—C6
C5—C4—C9—C3
C5—C4—C9—C8
151.1 (2)
20.3 (3)
C31—C41—C411—O42
−177.3 (3)
−178.3 (2)
2.4 (4)
C51—C41—C411—O41
C51—C41—C411—O42
C41—C51—C61—C11
−47.3 (4)
−91.9 (3)
32.3 (4)
0.8 (4)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
O41—H41···O1Wi
O1W—H11W···O1
O1W—H12W···O42ii
O2W—H21W···O1
O2W—H22W···O42iii
C9—H9···O1Wiv
0.90
0.83
0.82
0.90
0.90
0.98
0.93
0.93
1.71
2.08
1.94
2.10
2.33
2.55
2.51
2.42
2.609 (3)
2.894 (3)
2.754 (3)
2.991 (12)
3.233 (12)
3.298 (4)
3.145 (3)
2.737 (3)
179
167
172
179
178
133
126
100
C21—H21···O3v
C31—H31···O41
Symmetry codes: (i) x−1/2, −y−1/2, z+1/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) x, y+1, z; (v) x, y−1, z.
Acta Cryst. (2012). C68, o327–o331
sup-17