2,5-Bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole and its one-dimensional polymeric complex with ZnCl2

Article abstract of DOI:10.1107/S0108270113022105

2,5-Bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole (L), C ₂₆H₂₀N₄O, forms one-dimensional chains via two types of intermolecular π-π interactions. In catena- poly[[dichloridozinc(II)]-μ-2,5-bis[4-methyl-3-(pyridin-3

Full text of DOI:10.1107/S0108270113022105

metal-organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
synthesized a new 1,3,4-oxadiazole bridging ligand, namely
2,5-bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole (L),
(I). The combination of L with ZnCl2 afforded [ZnCl2L]n, (II),
which is a coordination polymer with one-dimensional chains
linked by ꢀ–ꢀ and C—HÁ Á Áꢀ interactions.
ISSN 0108-2701
2,5-Bis[4-methyl-3-(pyridin-3-yl)-
phenyl]-1,3,4-oxadiazole and its
one-dimensional polymeric complex
with ZnCl2
Shan Hou, Qi-Kui Liu, Yan-An Li, Jian-Ping Ma and Yu-Bin
Dong*
College of Chemistry, Chemical Engineering and Materials Science, Shandong
Normal University, Jinan 250014, People’s Republic of China
Correspondence e-mail: yubindong@sdnu.edu.cn
Received 22 December 2012
Accepted 7 August 2013
2,5-Bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole (L),
C26H20N4O, forms one-dimensional chains via two types of
intermolecular ꢀ–ꢀ interactions. In catena-poly[[dichlorido-
zinc(II)]-ꢁ-2,5-bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxa-
diazole], [ZnCl2(C26H20N4O)]n, synthesized by the com-
bination of L with ZnCl2, the ZnII centres are coordinated
by two Cl atoms and two N atoms from two L ligands.
[ZnCl2L]n forms one-dimensional P (plus) and M (minus)
helical chains, where the L ligand has different directions of
twist. The helical chains stack together via interchain ꢀ–ꢀ and
C—HÁ Á Áꢀ interactions.
2. Experimental
2.1. Synthesis and crystallization
Keywords: crystal structure; MOFs; coordination polymers;
helical chains.
For the preparation of (I), a mixture of 2,5-bis(3-bromo-4-
methylphenyl)-1,3,4-oxadiazole (4.08 g, 10.00 mmol), (pyri-
din-3-yl)boronic acid (2.71 g, 22.0 mmol), K2CO3 (4.15 g,
30.0 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol) in an EtOH–H2O
(2:1 v/v) system were stirred under N2 for 36 h under reflux.
After removal of the solvent under vacuum, the residue was
purified by silica-gel column chromatography using tetra-
hydrofuran (THF) and dichloromethane (DCM) (3:1 v/v) as
eluent to afford (I) (yield 3.23 g, 80.3%). A solution of (I)
(8.1 mg, 0.010 mmol) in CH2Cl2 (10 ml) was left for about 2 d
at room temperature, after which time colourless crystals were
obtained (yield 5.3 mg, 65.1%). IR (KBr pellet cmÀ1): 3041
(w), 1616 (ms), 1589 (s), 1499 (s), 1385 (vs), 1238 (s), 1073
(ms), 898 (ms), 810 (s), 734 (vs), 719 (s). 1H NMR (300 MHz,
CDCl3, 298 K, TMS): ꢂ 8.64–8.65 (t, 2H, –C5H4N), 8.08–8.210
(d, 1H, –benzeneH3), 7.98 (s, 1H, –benzeneH3), 7.72–7.74 (d,
1H, –benzeneH3), 7.46–7.49 (d, 1H, –C5H4N), 7.42–7.45 (t, 1H,
–benzeneH3), 2.36 (s, 3H, –CH3). Elemental analysis (%)
calculated for C26H20N4O: C 77.21, H 4.98, N 13.85; found:
C 77.42, H 4.82, N 13.85.
1. Introduction
Numerous coordination polymers designed and constructed
through crystal engineering have attracted significant atten-
tion because of their fascinating structural topologies (Chak-
rabary et al., 2011) and functional applications (Amouri et al.,
2012; Das et al., 2012). It is well known that the selection of
appropriate ligands as building blocks is a key point in the
design and synthesis of functional coordination polymers.
Over the past decade, the design and construction of rigid and
flexible organic ligands bridged by 1,3,4-oxadiazole have been
pursued due to the diversity of these ligands in coordination
chemistry and their applications in functional materials
(Jabbour et al., 2002; Hughes & Bryce, 2005; Du et al., 2010). It
is well known that ꢀ–ꢀ and C—HÁ Á Áꢀ interactions play an
important role in determining the arrangement of coordina-
tion polymers incorporating these ligands (Das et al., 2010;
Gathergood et al., 2003). In order to investigate how organic
ligands bridged by 1,3,4-oxadiazole affect the arrangement of
molecular complexes in self-assembled aggregates, we
For the preparation of (II), a solution of ZnCl2 (1.4 mg,
0.01 mmol) in MeOH (1 ml) was layered onto a solution of L
(4.0 mg, 0.01 mmol) in tetrahydrofuran (2 ml). The solutions
1108 # 2013 International Union of Crystallography
doi:10.1107/S0108270113022105
Acta Cryst. (2013). C69, 1108–1111

metal-organic compounds
Table 1
Experimental details.
(I)
(II)
Crystal data
Chemical formula
Mr
C26H20N4O
404.46
[ZnCl2(C26H20N4O)]
540.73
Crystal system, space group
Temperature (K)
Monoclinic, P21/c
298
12.786 (3), 7.8720 (18), 20.732 (5)
105.573 (3)
2010.2 (8)
4
Mo Kꢄ
0.08
0.50 Â 0.50 Â 0.13
Monoclinic, P21/n
173
17.779 (3), 7.3406 (14), 18.944 (4)
102.942 (2)
2409.6 (8)
4
Mo Kꢄ
1.27
0.40 Â 0.25 Â 0.02
˚
a, b, c (A)
ꢃ (ꢁ)
3
˚
V (A )
Z
Radiation type
ꢁ (mmÀ1
Crystal size (mm)
)
Data collection
Diffractometer
Bruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correction
Tmin, Tmax
Multi-scan (SADABS; Bruker, 2003)
0.959, 0.989
10264, 3790, 3079
Multi-scan (SADABS; Bruker, 2003)
0.596, 0.975
12117, 4524, 3375
No. of measured, independent and
observed [I > 2ꢅ(I)] reflections
Rint
0.023
0.608
0.047
0.608
À1
˚
(sin ꢆ/ꢇ)max (A
)
Refinement
R[F2 > 2ꢅ(F2)], wR(F2), S
No. of reflections
No. of parameters
0.044, 0.122, 1.03
3790
282
H-atom parameters constrained
0.043, 0.111, 1.01
4522
309
H-atom parameters constrained
H-atom treatment
˚
À3
Áꢈmax, Áꢈmin (e A
)
0.29, À0.23
0.45, À0.36
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and SHELXTL (Sheldrick, 2008).
were left for about 6 d at room temperature after which time
colourless crystals of (II) were obtained (yield 3.4 mg, 63%).
IR (KBr pellet cmÀ1): 2974 (w), 1616 (ms), 1550 (s), 1495 (vs),
1417 (vs), 1195 (s), 1036 (ms), 900 (s), 815 (s), 735 (s), 712(vs).
Elemental analysis (%) calculated for C26H20Cl2N4OZn: C
57.75, H 3.73, N 10.36; found: C 57.83, H 3.74, N 10.37.
idealized positions and included as riding atoms, with C—H =
˚
0.95 A and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and
˚
C—H = 0.98 A and Uiso(H) = 1.5Ueq(C) for methyl H atoms.
The initial torsion angles of the methyl groups were estab-
lished using a local difference Fourier calculation. In the
refinement, the methyl groups were allowed to rotate.
2.2. Refinement
3. Results and discussion
Crystal data, data collection and structure refinement
details are summarized in Table 1. H atoms attached to
anisotropically refined atoms were placed in geometrically
Within 2,5-bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadi-
azole, (I) (Fig. 1), the dihedral angles between the planes of
the pyridine and oxadiazole rings are 60.661 (6) and
Figure 2
Figure 1
The molecular structure of (I), showing the atom-numbering scheme.
Displacement ellipsoids are drawn at the 30% probability level.
The one-dimensional chain of (I), constructed by two kinds of ꢀ–ꢀ
interactions (red and green dashed lines in the electronic version of the
paper). H atoms have been omitted for clarity.
ꢀ
Acta Cryst. (2013). C69, 1108–1111
Hou et al.
C26H20N4O and [ZnCl2(C26H20N4O)] 1109

metal-organic compounds
Figure 3
The molecular structure of (II), showing the atom-numbering scheme.
Displacement ellipsoids are drawn at the 30% probability level.
1
1
2
1
2
1
2
1
2
1
2
[Symmetry code: (i) Àx + , y + , Àz + ; (ii) Àx + , y À , Àz + .]
2
58.169 (6)ꢁ for the N1- and N4-containing pyridine rings,
respectively, and the dihedral angles between the pyridine
rings and the adjacent benzene rings are 60.973 (5) and
51.894 (4)ꢁ. The two benzene rings of (I) are almost coplanar,
with a dihedral angle of 8.977 (4)ꢁ between the planes.
Molecules of (I) are arranged in chains via two kinds of ꢀ–ꢀ
interactions (Fig. 2). One type is between the oxadiazole ring
of one molecule and a benzene ring of an adjacent molecule
Figure 4
View of the one-dimensional P (plus) and M (minus) helices of (II), which
are assembled by different ligand twists and ZnII ions. H atoms have been
omitted for clarity.
˚
[centroid–centroid distance = 3.592 (1) A], while the other is
between a benzene ring of one molecule and the N4-
combined with ZnII ions to assemble right-handed (P) and
left-handed (M) Zn–mspda helical chains. Finally, the P- and
M-type helical chains are interlinked by carboxylate O atoms
to form a one-dimensional ladder.
The helical chains in (II) are arranged side-by-side along
the b axis (Fig. 5), where they interact via two kinds of ꢀ–ꢀ
interactions [centroid–centroid distances = 3.823 (1) and
containing pyridine ring of
[centroid–centroid distance = 3.858 (3) A].
a neighbouring molecule
˚
Compound (II) crystallizes with one ZnII centre in a
distorted tetrahedral environment (ZnCl2N2) involving two Cl
atoms (Cl1 and Cl2) and two N atoms from two L ligands [N1ii
1
and N4; symmetry code: (ii) Àx + 12, y À , Àz + 21] (Fig. 3). The
2
coordination behaviour of the ZnII atom is similar to that of
the HgII atom in Hg{2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole}I2
(Dong et al., 2003), which is coordinated by two N-atom
donors from two oxadiazole bridging ligands and two coor-
dinated iodide ligands.
3.556 (1) A]. The result is that a novel two-dimensional sheet
˚
is generated in the bc plane. It is similar to that observed in a
previously reported compound (Yang et al., 2011), which
forms helical chains that aggregate via interchain ꢀ–ꢀ inter-
actions to extend the dimensionality of the structure from one-
to two-dimensional. In (II), the two-dimensional sheets then
interact via C—HÁ Á Áꢀ interactions [HÁ Á Ácentroid distance =
Compared with the dihedral angles given above for (I),
those in (II) between the pyridine rings and the adjacent
benzene rings change to 53.464 (1) and 56.966 (1)ꢁ for the N1-
and N4-containing pyridine rings, respectively. Additionally,
the dihedral angle formed by the two benzene rings changes
from 8.977 (4)ꢁ in the free ligand to 11.887 (9)ꢁ in (II). In the
extended structure of (II), complex molecules are joined to
form a one-dimensional chain along the b axis (Fig. 4). It is
interesting that L has different directions of twist when
coordinated to the ZnII centre. It is also the origin of the
presence of P (plus) and M (minus) helices in (II). To our
knowledge, reports of such an arrangement of helical chains
are rare in ZnII frameworks (Yashima et al., 2008; Bishop,
2008). It is similar to that found in [Zn(mspda)(C2H7N)]n
[mspda2À is (E)-2,6-dimethyl-4-styrylpyridine-3,5-dicarboxyl-
ate; Zhang et al., 2012], which has two S- and R-type chiral
units from the axially prochiral mspda2À. These chiral units
˚
2.755 (6) A] along the b axis to form a novel coordination
polymer. The distance is similar to that observed in morphine
bis(1-naphthoate) (Gathergood et al., 2003), where the
˚
HÁ Á Ácentroid distances are in the range 2.80–3.07 A.
In summary, a new compound with P- and M-type helical
chains has been successfully obtained based on the new flex-
ible 1,3,4-oxadiazole-centred bridging ligand L and ZnCl2.
The helices assemble through interchain ꢀ–ꢀ and C—HÁ Á Áꢀ
interactions to form a novel coordination polymer. This study
demonstrates that ꢀ–ꢀ and C—HÁ Á Áꢀ interactions play an
important role in constructing coordination polymers.
This work was supported by the National Natural Science
Foundation of China (grant No. 21101100), the Shandong
Distinguished Middle-Aged and Young Scientist Encourage
ꢀ
1110 Hou et al. C26H20N4O and [ZnCl2(C26H20N4O)]
Acta Cryst. (2013). C69, 1108–1111

metal-organic compounds
Figure 5
A packing view of (II), constructed by interchain ꢀ–ꢀ interactions (red and green dashed lines in the electronic version of the paper) and C—HÁ Á Áꢀ
interactions (purple dashed lines in the electronic version of the paper). Some H atoms have been omitted.
Das, A., Jana, A. D., Seth, S. K., Dey, B., Choudhury, S. R., Kar, T.,
Mukhopadhyay, S., Singh, N. J., Hwang, I.-C. & Kim, K. S. (2010). J. Phys.
Chem. B, 114, 4166–4170.
Dong, Y.-B., Cheng, J.-Y., Ma, J.-P., Wang, H.-Y., Huang, R.-Q., Guo, D.-S. &
and Reward Foundation (grant No. BS2012CL035), ‘PCSIRT’
and Taishan scholars’ construction project special fund.
Smith, M. D. (2003). Solid State Sci. 5, 1177–1186.
Du, M., Wang, Q., Li, C.-P., Zhao, X.-J. & Ribas, J. (2010). Cryst. Growth Des.
10, 3285–3296.
Gathergood, N., Scammells, P. J. & Fallon, G. D. (2003). Acta Cryst. C59, o485–
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: EM3058). Services for accessing these data are
described at the back of the journal.
o487.
Hughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94–107.
Jabbour, G. E., Wang, J. F. & Peyghambarian, N. (2002). Appl. Phys. Lett. 80,
2026–2028.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Yang, R., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2011). Acta Cryst. C67, m176–
m180.
Yashima, E., Maeda, K. & Furusho, Y. (2008). Acc. Chem. Res. 41, 1166–
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ꢀ
Acta Cryst. (2013). C69, 1108–1111
Hou et al.
C26H20N4O and [ZnCl2(C26H20N4O)] 1111

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 1108-1111 [doi:10.1107/S0108270113022105]
2,5-Bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole and its one-
dimensional polymeric complex with ZnCl2
Shan Hou, Qi-Kui Liu, Yan-An Li, Jian-Ping Ma and Yu-Bin Dong
Computing details
For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction:
SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare
material for publication: SHELXTL (Sheldrick, 2008).
(I) 2,5-Bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole
Crystal data
C26H20N4O
Mr = 404.46
F(000) = 848
Dx = 1.336 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4084 reflections
θ = 2.6–27.8°
Monoclinic, P21/c
Hall symbol: -P2ybc
a = 12.786 (3) Å
b = 7.8720 (18) Å
c = 20.732 (5) Å
β = 105.573 (3)°
V = 2010.2 (8) Å3
Z = 4
µ = 0.08 mm−1
T = 298 K
Block, colourless
0.50 × 0.50 × 0.13 mm
Data collection
Bruker SMART CCD area-detector
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
phi and ω scans
10264 measured reflections
3790 independent reflections
3079 reflections with I > 2σ(I)
Rint = 0.023
θ
max = 25.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = −9→15
k = −9→9
T
min = 0.959, Tmax = 0.989
l = −25→25
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.044
wR(F2) = 0.122
S = 1.03
3790 reflections
282 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
Acta Cryst. (2013). C69, 1108-1111
sup-1

supplementary materials
w = 1/[σ2(Fo2) + (0.0635P)2 + 0.4318P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.29 e Å−3
Δρmin = −0.23 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.
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
C1
−0.12513 (15)
−0.1429
0.2667 (3)
0.2709
0.29172 (9)
0.3323
0.0602 (5)
0.072*
H1
C2
−0.03144 (16)
0.0145
0.1856 (3)
0.1398
0.28994 (8)
0.3286
0.0598 (5)
0.072*
H2
C3
−0.00664 (14)
0.0562
0.1734 (2)
0.1179
0.22925 (8)
0.2265
0.0508 (4)
0.061*
H3
C4
−0.07560 (12)
−0.16687 (13)
−0.2132
0.2439 (2)
0.3273 (2)
0.3774
0.17264 (7)
0.18080 (8)
0.1432
0.0403 (4)
0.0484 (4)
0.058*
C5
H5
C6
−0.05221 (12)
−0.12393 (12)
−0.22349 (15)
−0.2846
0.23559 (19)
0.1567 (2)
0.0623 (2)
0.1380
0.10603 (7)
0.05105 (8)
0.05632 (9)
0.0463
0.0384 (3)
0.0417 (4)
0.0575 (5)
0.086*
C7
C8
H8A
H8B
H8C
C9
−0.2121
0.0188
0.1009
0.086*
−0.2374
−0.0303
0.0250
0.086*
−0.09938 (13)
−0.1467
0.1609 (2)
0.1101
−0.01032 (8)
−0.0473
0.0448 (4)
0.054*
H9
C10
H10
C11
C12
H12
C13
C14
C15
C16
H16
C17
H17
C18
C19
H19A
H19B
−0.00730 (13)
0.0066
0.2381 (2)
0.2404
−0.01780 (7)
−0.0596
0.0436 (4)
0.052*
0.06540 (12)
0.04249 (12)
0.0911
0.31288 (18)
0.31020 (19)
0.3590
0.03691 (7)
0.09854 (7)
0.1355
0.0373 (3)
0.0383 (3)
0.046*
0.16280 (11)
0.31299 (12)
0.40979 (12)
0.49126 (13)
0.4819
0.39487 (19)
0.52824 (19)
0.60686 (19)
0.6629 (2)
0.6567
0.02775 (7)
0.05390 (7)
0.09681 (7)
0.06909 (8)
0.0231
0.0373 (3)
0.0381 (3)
0.0390 (3)
0.0484 (4)
0.058*
0.58554 (14)
0.6388
0.7274 (2)
0.7663
0.10996 (8)
0.0906
0.0518 (4)
0.062*
0.60463 (12)
0.70939 (14)
0.7680
0.7369 (2)
0.8139 (3)
0.7365
0.17899 (8)
0.21953 (9)
0.2210
0.0446 (4)
0.0619 (5)
0.093*
0.7046
0.8357
0.2642
0.093*
Acta Cryst. (2013). C69, 1108-1111
sup-2

supplementary materials
H19C
C20
C21
H21
C22
C23
H23
C24
H24
C25
H25
C26
H26
N1
0.7224
0.9186
0.1992
0.093*
0.52395 (12)
0.42699 (12)
0.3721
0.67559 (19)
0.61574 (19)
0.5807
0.20748 (7)
0.16563 (7)
0.1844
0.0387 (4)
0.0381 (3)
0.046*
0.53833 (12)
0.46033 (12)
0.3986
0.66639 (19)
0.7284 (2)
0.7819
0.28099 (7)
0.30991 (8)
0.2837
0.0392 (4)
0.0441 (4)
0.053*
0.47466 (14)
0.4229
0.7104 (2)
0.7511
0.37778 (8)
0.3980
0.0525 (4)
0.063*
0.56682 (16)
0.5761
0.6311 (2)
0.6202
0.41499 (9)
0.4608
0.0572 (5)
0.069*
0.62796 (13)
0.6804
0.5867 (2)
0.5428
0.32332 (8)
0.3044
0.0493 (4)
0.059*
−0.19268 (12)
0.19136 (11)
0.29032 (11)
0.64377 (12)
0.23554 (8)
0.3404 (2)
0.41233 (18)
0.50044 (18)
0.5689 (2)
0.46532 (13)
0.23861 (7)
−0.02684 (6)
−0.00966 (6)
0.38922 (7)
0.08148 (5)
0.0577 (4)
0.0460 (3)
0.0464 (3)
0.0582 (4)
0.0388 (3)
N2
N3
N4
O1
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.0610 (11)
0.0670 (12)
0.0478 (9)
0.0383 (8)
0.0382 (8)
0.0377 (8)
0.0401 (8)
0.0539 (10)
0.0455 (9)
0.0476 (9)
0.0373 (8)
0.0351 (7)
0.0373 (8)
0.0372 (8)
0.0383 (8)
0.0501 (9)
0.0458 (9)
0.0375 (8)
0.0436 (10)
0.0367 (8)
0.0343 (7)
0.0377 (8)
0.0378 (8)
0.0512 (10)
0.0628 (11)
0.0447 (9)
0.0441 (8)
0.0450 (7)
0.0840 (14)
0.0720 (13)
0.0608 (11)
0.0452 (9)
0.0658 (11)
0.0412 (8)
0.0406 (8)
0.0656 (12)
0.0482 (9)
0.0504 (9)
0.0391 (8)
0.0445 (8)
0.0414 (8)
0.0431 (8)
0.0409 (8)
0.0582 (10)
0.0631 (11)
0.0478 (9)
0.0804 (14)
0.0392 (8)
0.0426 (8)
0.0388 (8)
0.0481 (9)
0.0627 (11)
0.0675 (12)
0.0556 (10)
0.0849 (11)
0.0596 (8)
0.0404 (9)
−0.0090 (10)
0.0045 (10)
0.0059 (8)
−0.0086 (7)
−0.0018 (8)
0.0008 (6)
0.0216 (8)
0.0114 (8)
0.0116 (7)
0.0102 (6)
0.0087 (7)
0.0089 (6)
0.0093 (7)
0.0149 (8)
0.0044 (7)
0.0095 (7)
0.0095 (6)
0.0053 (6)
0.0073 (6)
0.0142 (6)
0.0117 (6)
0.0177 (7)
0.0236 (8)
0.0139 (7)
0.0154 (8)
0.0105 (6)
0.0124 (6)
0.0080 (6)
0.0087 (7)
0.0186 (8)
0.0090 (8)
0.0075 (7)
0.0167 (7)
0.0131 (6)
−0.0022 (9)
0.0102 (8)
0.0043 (8)
−0.0018 (6)
−0.0026 (8)
0.0001 (6)
−0.0019 (7)
−0.0101 (9)
−0.0062 (7)
−0.0013 (7)
0.0009 (6)
−0.0035 (6)
−0.0018 (6)
0.0040 (6)
0.0044 (6)
0.0018 (7)
−0.0003 (8)
−0.0012 (7)
−0.0065 (10)
0.0015 (6)
0.0034 (6)
−0.0015 (6)
0.0016 (7)
−0.0038 (8)
0.0021 (8)
−0.0022 (8)
−0.0084 (8)
−0.0037 (6)
C2
0.0387 (9)
0.0433 (9)
0.0375 (8)
0.0400 (8)
0.0356 (8)
0.0433 (8)
0.0533 (10)
0.0369 (8)
0.0321 (8)
0.0354 (8)
0.0330 (7)
0.0321 (7)
0.0365 (8)
0.0388 (8)
0.0403 (8)
0.0525 (10)
0.0499 (9)
0.0624 (11)
0.0404 (8)
0.0388 (8)
0.0398 (8)
0.0451 (9)
0.0468 (9)
0.0387 (9)
0.0450 (9)
0.0468 (8)
0.0350 (7)
C3
C4
C5
C6
C7
−0.0038 (7)
−0.0209 (9)
−0.0063 (7)
−0.0021 (7)
0.0023 (6)
−0.0010 (6)
0.0020 (6)
0.0021 (6)
0.0016 (7)
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C21
C22
C23
C24
C25
C26
N1
−0.0061 (8)
−0.0113 (8)
−0.0015 (7)
−0.0131 (9)
0.0026 (6)
0.0004 (6)
−0.0038 (6)
−0.0019 (7)
−0.0048 (8)
−0.0038 (10)
0.0055 (8)
−0.0035 (8)
−0.0059 (7)
N2
Acta Cryst. (2013). C69, 1108-1111
sup-3

supplementary materials
N3
N4
O1
0.0428 (7)
0.0580 (9)
0.0376 (5)
0.0618 (9)
0.0657 (10)
0.0476 (6)
0.0364 (7)
0.0440 (8)
0.0317 (5)
−0.0051 (6)
0.0060 (8)
−0.0034 (5)
0.0141 (6)
0.0019 (7)
0.0101 (4)
−0.0022 (6)
0.0035 (7)
−0.0001 (4)
Geometric parameters (Å, º)
C1—N1
C1—C2
1.336 (2)
C14—O1
1.3627 (17)
1.367 (3)
0.9300
C14—C15
C15—C21
C15—C16
C16—C17
C16—H16
C17—C18
C17—H17
C18—C20
C18—C19
C19—H19A
C19—H19B
C19—H19C
C20—C21
C20—C22
C21—H21
C22—C23
C22—C26
C23—C24
C23—H23
C24—C25
C24—H24
C25—N4
1.454 (2)
1.386 (2)
1.390 (2)
1.371 (2)
0.9300
C1—H1
C2—C3
1.381 (2)
0.9300
C2—H2
C3—C4
1.381 (2)
0.9300
C3—H3
C4—C5
1.388 (2)
0.9300
1.388 (2)
1.491 (2)
1.330 (2)
0.9300
C4—C6
1.405 (2)
1.504 (2)
0.9600
C5—N1
C5—H5
C6—C12
C6—C7
1.391 (2)
1.402 (2)
1.390 (2)
1.503 (2)
0.9600
0.9600
0.9600
C7—C9
1.391 (2)
1.487 (2)
0.9300
C7—C8
C8—H8A
C8—H8B
C8—H8C
C9—C10
C9—H9
C10—C11
C10—H10
C11—C12
C11—C13
C12—H12
C13—N2
C13—O1
C14—N3
0.9600
1.383 (2)
1.392 (2)
1.377 (2)
0.9300
0.9600
1.370 (2)
0.9300
1.390 (2)
0.9300
1.373 (3)
0.9300
1.385 (2)
1.460 (2)
0.9300
1.332 (2)
0.9300
C25—H25
C26—N4
1.334 (2)
0.9300
1.2867 (19)
1.3627 (17)
1.2896 (19)
C26—H26
N2—N3
1.4025 (19)
N1—C1—C2
N1—C1—H1
C2—C1—H1
C1—C2—C3
C1—C2—H2
C3—C2—H2
C4—C3—C2
C4—C3—H3
C2—C3—H3
C3—C4—C5
C3—C4—C6
C5—C4—C6
N1—C5—C4
N1—C5—H5
C4—C5—H5
123.92 (16)
118.0
C21—C15—C16
C21—C15—C14
C16—C15—C14
C17—C16—C15
C17—C16—H16
C15—C16—H16
C16—C17—C18
C16—C17—H17
C18—C17—H17
C17—C18—C20
C17—C18—C19
C20—C18—C19
C18—C19—H19A
C18—C19—H19B
H19A—C19—H19B
118.70 (14)
121.67 (13)
119.44 (14)
119.62 (15)
120.2
118.0
118.33 (16)
120.8
120.8
120.2
119.71 (16)
120.1
122.63 (15)
118.7
120.1
118.7
116.90 (14)
121.90 (14)
121.19 (14)
124.52 (16)
117.7
117.99 (14)
118.80 (14)
123.21 (15)
109.5
109.5
117.7
109.5
Acta Cryst. (2013). C69, 1108-1111
sup-4

supplementary materials
C12—C6—C7
C12—C6—C4
C7—C6—C4
119.68 (13)
118.81 (13)
121.51 (13)
118.33 (14)
118.81 (14)
122.82 (14)
109.5
C18—C19—H19C
109.5
H19A—C19—H19C
H19B—C19—H19C
C21—C20—C18
C21—C20—C22
C18—C20—C22
C15—C21—C20
C15—C21—H21
C20—C21—H21
C23—C22—C26
C23—C22—C20
C26—C22—C20
C24—C23—C22
C24—C23—H23
C22—C23—H23
C25—C24—C23
C25—C24—H24
C23—C24—H24
N4—C25—C24
N4—C25—H25
C24—C25—H25
N4—C26—C22
N4—C26—H26
C22—C26—H26
C5—N1—C1
109.5
109.5
C9—C7—C6
119.10 (14)
117.85 (13)
123.02 (13)
121.87 (14)
119.1
C9—C7—C8
C6—C7—C8
C7—C8—H8A
C7—C8—H8B
H8A—C8—H8B
C7—C8—H8C
H8A—C8—H8C
H8B—C8—H8C
C10—C9—C7
C10—C9—H9
C7—C9—H9
109.5
109.5
119.1
109.5
116.95 (14)
121.45 (13)
121.50 (14)
119.54 (15)
120.2
109.5
109.5
121.76 (14)
119.1
119.1
120.2
C9—C10—C11
C9—C10—H10
C11—C10—H10
C12—C11—C10
C12—C11—C13
C10—C11—C13
C11—C12—C6
C11—C12—H12
C6—C12—H12
N2—C13—O1
N2—C13—C11
O1—C13—C11
N3—C14—O1
N3—C14—C15
O1—C14—C15
120.14 (14)
119.9
118.67 (16)
120.7
119.9
120.7
119.05 (14)
121.72 (13)
119.23 (13)
121.01 (13)
119.5
123.82 (16)
118.1
118.1
124.47 (16)
117.8
119.5
117.8
112.51 (13)
127.97 (13)
119.51 (12)
112.19 (13)
128.18 (13)
119.54 (12)
116.57 (15)
106.21 (12)
106.47 (12)
116.55 (15)
102.62 (11)
C13—N2—N3
C14—N3—N2
C25—N4—C26
C14—O1—C13
(II) catena-Poly[[dichloridozinc(II)]-µ-2,5-bis[4-methyl-3-(pyridin-3-yl)phenyl]-1,3,4-oxadiazole]
Crystal data
ZnCl2(C26H20N4O)]
Mr = 540.73
F(000) = 1104
Dx = 1.491 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2427 reflections
θ = 2.4–24.2°
Monoclinic, P21/n
Hall symbol: -P2yn
a = 17.779 (3) Å
b = 7.3406 (14) Å
c = 18.944 (4) Å
β = 102.942 (2)°
V = 2409.6 (8) Å3
Z = 4
µ = 1.27 mm−1
T = 173 K
Plan, colourless
0.40 × 0.25 × 0.02 mm
Data collection
CCD area detector
Absorption correction: multi-scan
diffractometer
(SADABS; Bruker, 2003)
Radiation source: fine-focus sealed tube
Graphite monochromator
phi and ω scans
Tmin = 0.596, Tmax = 0.975
12117 measured reflections
4524 independent reflections
3375 reflections with I > 2σ(I)
Acta Cryst. (2013). C69, 1108-1111
sup-5

supplementary materials
Rint = 0.047
max = 25.6°, θmin = 1.4°
k = −8→7
l = −18→23
θ
h = −20→21
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.043
wR(F2) = 0.111
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.01
4522 reflections
309 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0548P)2 + 0.1756P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.45 e Å−3
Δρmin = −0.36 e Å−3
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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
C1
0.16126 (18)
0.1209
0.6976 (5)
0.6833
0.26063 (18)
0.2187
0.0328 (8)
0.039*
H1
C2
0.2280 (2)
0.2347
0.7857 (6)
0.8265
0.25466 (19)
0.2089
0.0431 (10)
0.052*
H2
C3
0.2849 (2)
0.3313
0.8137 (5)
0.8736
0.31622 (19)
0.3129
0.0390 (9)
0.047*
H3
C4
0.27476 (16)
0.20737 (16)
0.2005
0.7550 (4)
0.6597 (4)
0.6118
0.38297 (16)
0.38309 (16)
0.4278
0.0247 (7)
0.0246 (7)
0.030*
C5
H5
C6
0.33366 (17)
0.31546 (17)
0.23458 (18)
0.2046
0.7906 (4)
0.8769 (4)
0.9378 (5)
0.8329
0.45015 (16)
0.51069 (17)
0.51220 (19)
0.5223
0.0223 (7)
0.0246 (7)
0.0354 (9)
0.053*
C7
C8
H8A
H8B
H8C
C9
0.2099
0.9901
0.4651
0.053*
0.2369
1.0298
0.5501
0.053*
0.37515 (18)
0.3636
0.9106 (5)
0.9689
0.57054 (17)
0.6116
0.0274 (8)
0.033*
H9
C10
H10
C11
C12
H12
C13
0.45045 (17)
0.4899
0.8624 (4)
0.8878
0.57237 (16)
0.6140
0.0250 (7)
0.030*
0.46819 (17)
0.41013 (16)
0.4225
0.7764 (4)
0.7427 (4)
0.6860
0.51290 (16)
0.45214 (16)
0.4111
0.0223 (7)
0.0224 (7)
0.027*
0.54849 (17)
0.7289 (4)
0.51408 (16)
0.0220 (7)
Acta Cryst. (2013). C69, 1108-1111
sup-6

supplementary materials
C14
C15
C16
H16
C17
H17
C18
C19
H19A
H19B
H19C
C20
C21
H21
C22
C23
H23
C24
H24
C25
H25
C26
H26
Cl1
0.64252 (16)
0.68035 (17)
0.76060 (17)
0.7914
0.6395 (4)
0.5769 (4)
0.5720 (4)
0.6053
0.47064 (16)
0.41447 (16)
0.42672 (17)
0.4726
0.0214 (7)
0.0224 (7)
0.0249 (7)
0.030*
0.79496 (18)
0.8497
0.5185 (4)
0.5136
0.37161 (18)
0.3808
0.0274 (7)
0.033*
0.75261 (18)
0.79327 (18)
0.7984
0.4716 (4)
0.4310 (5)
0.5435
0.30340 (17)
0.24346 (18)
0.2171
0.0249 (7)
0.0312 (8)
0.047*
0.7632
0.3420
0.2101
0.047*
0.8446
0.3811
0.2642
0.047*
0.67094 (17)
0.63684 (17)
0.5822
0.4712 (4)
0.5235 (4)
0.5227
0.29199 (16)
0.34775 (16)
0.3400
0.0217 (7)
0.0229 (7)
0.027*
0.61998 (17)
0.6204 (2)
0.6543
0.4131 (4)
0.4928 (5)
0.5912
0.22197 (16)
0.15529 (18)
0.1525
0.0234 (7)
0.0316 (8)
0.038*
0.57161 (19)
0.5717
0.4284 (5)
0.4811
0.09361 (18)
0.0478
0.0337 (8)
0.040*
0.52253 (18)
0.4895
0.2863 (5)
0.2408
0.09907 (17)
0.0562
0.0309 (8)
0.037*
0.56744 (16)
0.5649
0.2750 (4)
0.2228
0.22232 (16)
0.2676
0.0226 (7)
0.027*
0.43174 (5)
0.49046 (5)
0.15169 (13)
0.60893 (14)
0.67166 (14)
0.51988 (13)
0.56427 (11)
0.44697 (2)
−0.15244 (14)
−0.14652 (13)
0.6314 (4)
0.7419 (4)
0.6846 (4)
0.2103 (4)
0.6635 (3)
−0.00636 (5)
0.06523 (5)
0.27360 (4)
0.32396 (14)
0.56605 (13)
0.53745 (14)
0.16266 (13)
0.45198 (10)
0.169115 (19)
0.0459 (3)
0.0363 (2)
0.0257 (6)
0.0275 (6)
0.0268 (6)
0.0251 (6)
0.0220 (5)
0.02624 (14)
Cl2
N1
N2
N3
N4
O1
Zn1
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.0243 (17)
0.038 (2)
0.045 (2)
0.0259 (18)
−0.0039 (16)
−0.0107 (19)
−0.0132 (18)
0.0017 (14)
−0.0009 (14)
0.0046 (17)
0.0043 (16)
0.0058 (13)
0.0056 (14)
0.0062 (13)
0.0116 (14)
0.0151 (17)
0.0156 (15)
0.0048 (14)
0.0067 (14)
0.0064 (13)
0.0058 (14)
0.0011 (13)
0.0040 (13)
0.0018 (16)
0.0120 (18)
0.0080 (18)
0.0024 (14)
0.0013 (14)
0.0031 (13)
0.0044 (14)
−0.0053 (17)
−0.0050 (14)
0.0015 (14)
0.0024 (13)
0.0014 (13)
0.0012 (13)
0.0027 (13)
0.0041 (13)
C2
0.061 (3)
0.029 (2)
C3
0.0313 (19)
0.0213 (16)
0.0236 (16)
0.0232 (16)
0.0261 (16)
0.0284 (18)
0.0341 (19)
0.0275 (17)
0.0243 (16)
0.0238 (16)
0.0265 (17)
0.0181 (15)
0.0220 (16)
0.050 (3)
0.034 (2)
C4
0.0289 (19)
0.0288 (19)
0.0222 (18)
0.0207 (18)
0.040 (2)
0.0244 (17)
0.0217 (17)
0.0221 (17)
0.0295 (18)
0.042 (2)
C5
−0.0021 (14)
−0.0058 (13)
−0.0020 (14)
−0.0009 (16)
−0.0057 (16)
−0.0041 (14)
−0.0041 (13)
−0.0025 (13)
−0.0027 (14)
−0.0015 (13)
0.0012 (14)
C6
C7
C8
C9
0.0291 (19)
0.0269 (19)
0.0219 (17)
0.0232 (18)
0.0223 (18)
0.0218 (17)
0.0205 (17)
0.0232 (18)
0.0203 (17)
0.0216 (17)
0.0210 (16)
0.0175 (16)
0.0229 (17)
0.0242 (17)
C10
C11
C12
C13
C14
C15
Acta Cryst. (2013). C69, 1108-1111
sup-7

supplementary materials
C16
C17
C18
C19
C20
C21
C22
C23
C24
C25
C26
Cl1
Cl2
N1
0.0215 (16)
0.0194 (16)
0.0232 (16)
0.0256 (17)
0.0221 (16)
0.0176 (15)
0.0204 (16)
0.0331 (19)
0.0354 (19)
0.0260 (17)
0.0167 (15)
0.0396 (5)
0.0231 (18)
0.0277 (19)
0.0200 (18)
0.0270 (19)
0.0178 (17)
0.0211 (18)
0.0261 (18)
0.031 (2)
0.0267 (18)
0.0350 (19)
0.0326 (19)
0.043 (2)
−0.0029 (14)
−0.0014 (14)
0.0003 (13)
−0.0021 (15)
−0.0001 (13)
−0.0001 (13)
0.0043 (14)
−0.0017 (16)
0.0021 (17)
−0.0004 (16)
0.0026 (14)
0.0066 (5)
−0.0017 (14)
0.0061 (14)
0.0085 (14)
0.0125 (16)
0.0051 (13)
0.0040 (13)
0.0102 (13)
0.0101 (16)
0.0070 (15)
0.0015 (14)
0.0044 (13)
0.0008 (4)
0.0055 (14)
0.0001 (15)
0.0014 (14)
−0.0061 (16)
0.0026 (13)
0.0041 (14)
0.0003 (14)
0.0019 (16)
0.0052 (16)
−0.0003 (15)
0.0002 (14)
−0.0189 (5)
0.0037 (4)
0.0251 (17)
0.0293 (18)
0.0261 (18)
0.032 (2)
0.044 (2)
0.0216 (18)
0.0217 (18)
0.0204 (17)
0.0312 (5)
0.0283 (5)
0.0269 (15)
0.0190 (14)
0.0237 (15)
0.0223 (15)
0.0196 (11)
0.0227 (2)
0.043 (2)
0.0308 (19)
0.0636 (7)
0.0419 (6)
0.0319 (17)
0.0376 (18)
0.0332 (17)
0.0341 (17)
0.0271 (13)
0.0357 (3)
0.0360 (5)
0.0177 (13)
0.0255 (14)
0.0226 (14)
0.0187 (13)
0.0183 (10)
0.0189 (2)
0.0047 (4)
0.0015 (4)
0.0001 (12)
0.0001 (13)
−0.0003 (12)
0.0012 (12)
−0.0010 (9)
0.00116 (17)
0.0037 (11)
0.0046 (12)
0.0032 (12)
0.0045 (11)
0.0020 (9)
0.0035 (12)
−0.0013 (12)
0.0009 (12)
−0.0012 (12)
−0.0011 (9)
−0.00337 (17)
N2
N3
N4
O1
Zn1
0.00174 (15)
Geometric parameters (Å, º)
C1—N1
C1—C2
1.340 (4)
C15—C21
C15—C16
C16—C17
C16—H16
C17—C18
C17—H17
C18—C20
C18—C19
C19—H19A
C19—H19B
C19—H19C
C20—C21
C20—C22
C21—H21
C22—C26
C22—C23
C23—C24
C23—H23
C24—C25
C24—H24
C25—N4
1.383 (4)
1.378 (5)
0.9500
1.394 (4)
1.380 (4)
0.9500
C1—H1
C2—C3
1.377 (5)
0.9500
C2—H2
C3—C4
1.385 (4)
0.9500
1.385 (4)
0.9500
C3—H3
C4—C5
1.419 (4)
1.506 (4)
0.9800
1.388 (4)
1.479 (4)
1.335 (4)
0.9500
C4—C6
C5—N1
C5—H5
C6—C12
C6—C7
0.9800
0.9800
1.397 (4)
1.410 (4)
1.391 (4)
1.512 (4)
0.9800
1.385 (4)
1.491 (4)
0.9500
C7—C9
C7—C8
1.379 (4)
1.393 (4)
1.374 (5)
0.9500
C8—H8A
C8—H8B
C8—H8C
C9—C10
C9—H9
C10—C11
C10—H10
C11—C12
C11—C13
C12—H12
C13—N2
C13—O1
C14—N3
0.9800
0.9800
1.377 (4)
0.9500
1.379 (5)
0.9500
1.388 (4)
0.9500
1.338 (4)
0.9500
C25—H25
C26—N4
1.386 (4)
1.465 (4)
0.9500
1.338 (4)
0.9500
C26—H26
Cl1—Zn1
Cl2—Zn1
N1—Zn1i
N2—N3
2.2040 (10)
2.2111 (10)
2.054 (2)
1.409 (3)
1.288 (4)
1.357 (3)
1.298 (4)
Acta Cryst. (2013). C69, 1108-1111
sup-8

supplementary materials
C14—O1
1.368 (3)
1.455 (4)
N4—Zn1
Zn1—N1ii
2.073 (3)
2.054 (2)
C14—C15
N1—C1—C2
N1—C1—H1
C2—C1—H1
C3—C2—C1
121.9 (3)
119.1
C15—C16—H16
C16—C17—C18
C16—C17—H17
C18—C17—H17
C17—C18—C20
C17—C18—C19
C20—C18—C19
C18—C19—H19A
C18—C19—H19B
120.3
122.4 (3)
118.8
119.1
118.9 (3)
120.6
118.8
C3—C2—H2
C1—C2—H2
C2—C3—C4
117.8 (3)
120.0 (3)
122.1 (3)
109.5
120.6
120.4 (3)
119.8
C2—C3—H3
C4—C3—H3
C3—C4—C5
119.8
109.5
116.6 (3)
121.2 (3)
122.2 (3)
123.7 (3)
118.1
H19A—C19—H19B
C18—C19—H19C
H19A—C19—H19C
H19B—C19—H19C
C21—C20—C18
C21—C20—C22
C18—C20—C22
C15—C21—C20
C15—C21—H21
C20—C21—H21
C26—C22—C23
C26—C22—C20
C23—C22—C20
C24—C23—C22
C24—C23—H23
C22—C23—H23
C23—C24—C25
C23—C24—H24
C25—C24—H24
N4—C25—C24
N4—C25—H25
C24—C25—H25
N4—C26—C22
N4—C26—H26
C22—C26—H26
C5—N1—C1
109.5
C3—C4—C6
109.5
C5—C4—C6
109.5
N1—C5—C4
N1—C5—H5
C4—C5—H5
C12—C6—C7
C12—C6—C4
C7—C6—C4
109.5
119.4 (3)
118.4 (3)
122.2 (3)
121.7 (3)
119.2
118.1
119.4 (3)
118.4 (3)
122.2 (3)
118.1 (3)
119.2 (3)
122.7 (3)
109.5
C9—C7—C6
119.2
C9—C7—C8
117.0 (3)
118.9 (3)
124.1 (3)
119.8 (3)
120.1
C6—C7—C8
C7—C8—H8A
C7—C8—H8B
H8A—C8—H8B
C7—C8—H8C
H8A—C8—H8C
H8B—C8—H8C
C10—C9—C7
C10—C9—H9
C7—C9—H9
C9—C10—C11
C9—C10—H10
C11—C10—H10
C12—C11—C10
C12—C11—C13
C10—C11—C13
C11—C12—C6
C11—C12—H12
C6—C12—H12
N2—C13—O1
N2—C13—C11
O1—C13—C11
N3—C14—O1
N3—C14—C15
O1—C14—C15
C21—C15—C16
109.5
109.5
109.5
120.1
109.5
119.1 (3)
120.5
109.5
122.3 (3)
118.8
120.5
122.2 (3)
118.9
118.8
119.5 (3)
120.2
118.9
123.9 (3)
118.1
120.2
119.5 (3)
120.8 (3)
119.6 (3)
121.1 (3)
119.4
118.1
118.4 (3)
120.4 (2)
121.1 (2)
106.3 (2)
105.9 (2)
118.0 (3)
120.5 (2)
121.4 (2)
102.5 (2)
100.39 (10)
111.14 (8)
105.91 (7)
C5—N1—Zn1i
C1—N1—Zn1i
C13—N2—N3
119.4
C14—N3—N2
113.0 (3)
129.6 (3)
117.4 (3)
112.3 (3)
130.1 (3)
117.5 (3)
119.2 (3)
C26—N4—C25
C26—N4—Zn1
C25—N4—Zn1
C13—O1—C14
N1ii—Zn1—N4
N1ii—Zn1—Cl1
N4—Zn1—Cl1
Acta Cryst. (2013). C69, 1108-1111
sup-9

supplementary materials
C21—C15—C14
C16—C15—C14
C17—C16—C15
C17—C16—H16
120.2 (3)
120.7 (3)
119.5 (3)
120.3
N1ii—Zn1—Cl2
N4—Zn1—Cl2
Cl1—Zn1—Cl2
107.72 (8)
108.18 (7)
121.42 (4)
N1—C1—C2—C3
−3.0 (6)
−0.4 (6)
3.5 (5)
C19—C18—C20—C22
C16—C15—C21—C20
C14—C15—C21—C20
C18—C20—C21—C15
C22—C20—C21—C15
C21—C20—C22—C26
C18—C20—C22—C26
C21—C20—C22—C23
C18—C20—C22—C23
C26—C22—C23—C24
C20—C22—C23—C24
C22—C23—C24—C25
C23—C24—C25—N4
C23—C22—C26—N4
C20—C22—C26—N4
C4—C5—N1—C1
6.0 (5)
C1—C2—C3—C4
−2.2 (5)
177.0 (3)
0.2 (5)
C2—C3—C4—C5
C2—C3—C4—C6
−177.4 (3)
−3.6 (5)
177.2 (3)
−51.4 (4)
127.7 (3)
126.2 (4)
−54.7 (4)
−0.1 (5)
−177.7 (3)
178.3 (3)
0.7 (5)
C3—C4—C5—N1
179.2 (3)
−55.0 (4)
124.0 (3)
123.3 (3)
−57.6 (4)
−2.2 (5)
179.4 (3)
0.5 (5)
C6—C4—C5—N1
C3—C4—C6—C12
C5—C4—C6—C12
C3—C4—C6—C7
C5—C4—C6—C7
C12—C6—C7—C9
C4—C6—C7—C9
C12—C6—C7—C8
C4—C6—C7—C8
1.0 (5)
2.7 (5)
C6—C7—C9—C10
C8—C7—C9—C10
C7—C9—C10—C11
C9—C10—C11—C12
C9—C10—C11—C13
C10—C11—C12—C6
C13—C11—C12—C6
C7—C6—C12—C11
C4—C6—C12—C11
C12—C11—C13—N2
C10—C11—C13—N2
C12—C11—C13—O1
C10—C11—C13—O1
N3—C14—C15—C21
O1—C14—C15—C21
N3—C14—C15—C16
O1—C14—C15—C16
C21—C15—C16—C17
C14—C15—C16—C17
C15—C16—C17—C18
C16—C17—C18—C20
C16—C17—C18—C19
C17—C18—C20—C21
C19—C18—C20—C21
C17—C18—C20—C22
−0.1 (5)
−178.6 (3)
−0.3 (5)
1.0 (5)
−178.9 (3)
0.4 (5)
C4—C5—N1—Zn1i
−178.5 (2)
3.0 (5)
C2—C1—N1—C5
178.6 (3)
−1.2 (5)
−178.8 (3)
0.8 (5)
C2—C1—N1—Zn1i
O1—C13—N2—N3
C11—C13—N2—N3
O1—C14—N3—N2
C15—C14—N3—N2
C13—N2—N3—C14
C22—C26—N4—C25
C22—C26—N4—Zn1
C24—C25—N4—C26
C24—C25—N4—Zn1
N2—C13—O1—C14
C11—C13—O1—C14
N3—C14—O1—C13
C15—C14—O1—C13
C26—N4—Zn1—N1ii
C25—N4—Zn1—N1ii
C26—N4—Zn1—Cl1
C25—N4—Zn1—Cl1
C26—N4—Zn1—Cl2
C25—N4—Zn1—Cl2
−178.1 (3)
1.2 (3)
−177.7 (3)
0.4 (3)
178.5 (3)
−176.4 (3)
6.0 (5)
177.6 (3)
−1.0 (3)
−1.2 (4)
177.0 (2)
−0.7 (5)
−178.9 (3)
−1.0 (3)
178.1 (3)
0.3 (3)
4.7 (4)
−172.9 (3)
175.3 (3)
−7.6 (4)
−5.5 (5)
171.6 (3)
1.6 (5)
−177.3 (3)
94.5 (2)
−87.3 (2)
−149.8 (2)
28.4 (3)
−18.2 (2)
160.0 (2)
−177.6 (3)
1.1 (5)
−3.1 (5)
174.4 (3)
2.4 (4)
−175.0 (3)
−176.6 (3)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.
Acta Cryst. (2013). C69, 1108-1111
sup-10

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