Syntheses and structures of three macrocyclic supra­molecular com­plexes and one Zn^II-containing coordination polymer generated from a semi-rigid multidentate N-containing ligand

Semirigid organic ligands can adopt different conformations to construct coordination polymers with more diverse structures when com­pared to those constructed from rigid ligands. A new asymmetric semirigid organic ligand, 4-{2-[(pyridin-3-yl)meth­yl]-2H-tetra­zol-5-yl}pyridine (L), has been prepared and used to synthesize three bimetallic macrocyclic com­plexes and one coordination polymer, namely, bis­(μ-4-{2-[(pyridin-3-yl)meth­yl]-2H-tetra­zol-5-yl}pyridine)­bis­[di­chlorido­zinc(II)] di­chloro­methane disolvate, [Zn₂Cl₄(C₁₂H₁₀N₆)₂]·2CH₂Cl₂, (I), the analogous chloro­form monosolvate, [Zn₂Cl₄(C₁₂H₁₀N₆)₂]·CHCl₃, (II), bis­(μ-4-{2-[(pyridin-3-yl)meth­yl]-2H-tetra­zol-5-yl}pyridine)­bis­[di­iodido­zinc(II)] di­chloro­methane disolvate, [Zn₂I₄(C₁₂H₁₀N₆)₂]·2CH₂Cl₂, (III), and catena-poly[[[di­iodido­zinc(II)]-μ-4-{2-[(pyridin-3-yl)meth­yl]-2H-tetra­zol-5-yl}pyridine] chloro­form monosolvate], {[ZnI₂(C₁₂H₁₀N₆)]·CHCl₃}_n, (IV), by solution reaction with ZnX₂ (X = Cl and I) in a CH₂Cl₂/CH₃OH or CHCl₃/CH₃OH mixed solvent system at room temperature. Complex (I) is isomorphic with com­plex (III) and has a bimetallic ring possessing similar coordination environments for both of the Zn^II cations. Although com­plex (II) also contains a bimetallic ring, the two Zn^II cations have different coordination environments. Under the influence of the I⁻ anion and guest CHCl₃ mol­ecule, com­plex (IV) displays a significantly different structure with respect to com­plexes (I)–(III). C—H...Cl and C—H...N hydrogen bonds, and π–π stacking or C—Cl...π inter­actions exist in com­plexes (I)–(IV), and these weak inter­actions play an important role in the three-dimensional structures of (I)–(IV) in the solid state. In addition, the fluorescence properties of L and com­plexes (I)–(IV) were investigated.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for L; APEX2 (Bruker, 2012) for (I), (II), (III), (IV). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for L; APEX2 (Bruker, 2012) for (I), (II), (III), (IV). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for L; SAINT (Bruker, 2012) for (I), (II), (III), (IV). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for L; SHELXT (Sheldrick, 2015a) for (I), (II), (III), (IV). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for L; SHELXL2018 (Sheldrick, 2015b) for (I), (II), (III), (IV). Molecular graphics: OLEX2 (Dolomanov et al., 2009) for L. Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for L; SHELXL2018 (Sheldrick, 2015b) for (I), (II), (III), (IV).

4-{2-[(Pyridin-3-yl)methyl]-2H-tetrazol-5-yl}pyridine (L)

Crystal data

C12H10N6	F(000) = 496
Mr = 238.26	Dx = 1.421 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.7529 (8) Å	Cell parameters from 1274 reflections
b = 6.6451 (4) Å	θ = 7.4–70.9°
c = 12.2086 (9) Å	µ = 0.76 mm^−1
β = 93.634 (6)°	T = 150 K
V = 1113.49 (12) Å^3	Plate, clear light colourless
Z = 4	0.43 × 0.42 × 0.3 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	2096 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1698 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 16.0793 pixels mm^-1	θmax = 71.0°, θmin = 3.2°
ω scans	h = −16→15
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −7→6
Tmin = 0.901, Tmax = 1.000	l = −14→13
3957 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.2666P] where P = (Fo^2 + 2Fc^2)/3
2096 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.23 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 > 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.

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

	x	y	z	Uiso*/Ueq
N1	0.33180 (11)	0.1437 (2)	0.22151 (12)	0.0273 (4)
N2	0.25713 (11)	0.1440 (2)	0.28427 (12)	0.0273 (4)
N3	0.28153 (12)	0.1329 (2)	0.39120 (13)	0.0308 (4)
N4	0.37733 (12)	0.1234 (2)	0.40005 (13)	0.0291 (4)
N5	0.04932 (12)	−0.3028 (3)	0.11399 (13)	0.0350 (4)
N6	0.70510 (12)	0.1196 (2)	0.21955 (14)	0.0321 (4)
C1	0.40641 (13)	0.1302 (2)	0.29627 (15)	0.0244 (4)
C2	0.15597 (13)	0.1724 (3)	0.24077 (16)	0.0316 (4)
H2A	0.1488	0.3051	0.2082	0.038*
H2B	0.1127	0.1638	0.3003	0.038*
C3	0.07501 (14)	−0.1529 (3)	0.18343 (15)	0.0304 (4)
H3	0.0561	−0.1623	0.2550	0.037*
C4	0.12788 (12)	0.0150 (3)	0.15566 (15)	0.0269 (4)
C5	0.15492 (14)	0.0302 (3)	0.04871 (15)	0.0331 (5)
H5	0.1897	0.1415	0.0266	0.040*
C6	0.12963 (15)	−0.1217 (3)	−0.02483 (16)	0.0363 (5)
H6	0.1473	−0.1152	−0.0970	0.044*
C7	0.07721 (14)	−0.2841 (3)	0.01147 (16)	0.0357 (5)
H7	0.0604	−0.3861	−0.0384	0.043*
C8	0.67852 (14)	0.1148 (3)	0.32269 (16)	0.0319 (4)
H8	0.7275	0.1100	0.3788	0.038*
C9	0.58292 (14)	0.1164 (3)	0.35186 (15)	0.0286 (4)
H9	0.5685	0.1111	0.4252	0.034*
C10	0.50894 (13)	0.1261 (2)	0.26889 (14)	0.0238 (4)
C11	0.53466 (14)	0.1324 (3)	0.16082 (15)	0.0277 (4)
H11	0.4872	0.1394	0.1032	0.033*
C12	0.63253 (14)	0.1280 (3)	0.14075 (16)	0.0301 (4)
H12	0.6491	0.1310	0.0681	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0273 (8)	0.0232 (8)	0.0317 (8)	0.0000 (6)	0.0052 (6)	−0.0023 (6)
N2	0.0263 (8)	0.0213 (8)	0.0347 (8)	−0.0011 (6)	0.0064 (6)	−0.0025 (6)
N3	0.0326 (9)	0.0292 (9)	0.0313 (8)	−0.0006 (7)	0.0079 (7)	−0.0017 (6)
N4	0.0288 (8)	0.0278 (8)	0.0312 (8)	0.0009 (6)	0.0051 (6)	−0.0003 (6)
N5	0.0350 (9)	0.0376 (9)	0.0323 (8)	−0.0104 (7)	0.0029 (7)	−0.0003 (7)
N6	0.0290 (8)	0.0255 (9)	0.0423 (9)	−0.0010 (7)	0.0054 (7)	−0.0002 (7)
C1	0.0272 (9)	0.0171 (8)	0.0291 (9)	0.0000 (7)	0.0030 (7)	−0.0013 (6)
C2	0.0251 (9)	0.0301 (10)	0.0401 (10)	0.0016 (8)	0.0056 (8)	−0.0009 (8)
C3	0.0296 (10)	0.0376 (11)	0.0244 (9)	−0.0047 (8)	0.0036 (7)	0.0023 (8)
C4	0.0207 (8)	0.0289 (10)	0.0311 (9)	0.0021 (7)	0.0006 (7)	0.0037 (7)
C5	0.0283 (9)	0.0358 (11)	0.0357 (10)	−0.0037 (8)	0.0046 (8)	0.0088 (8)
C6	0.0313 (10)	0.0496 (13)	0.0285 (10)	−0.0046 (9)	0.0053 (8)	0.0015 (8)
C7	0.0321 (10)	0.0432 (12)	0.0318 (10)	−0.0046 (9)	0.0021 (8)	−0.0043 (9)
C8	0.0300 (10)	0.0267 (10)	0.0387 (11)	0.0017 (8)	−0.0011 (8)	−0.0013 (8)
C9	0.0332 (10)	0.0230 (9)	0.0298 (9)	−0.0007 (7)	0.0024 (8)	−0.0028 (7)
C10	0.0275 (9)	0.0125 (9)	0.0318 (9)	0.0000 (6)	0.0043 (7)	−0.0008 (6)
C11	0.0313 (10)	0.0203 (9)	0.0315 (9)	0.0018 (7)	0.0017 (7)	0.0022 (7)
C12	0.0341 (10)	0.0230 (9)	0.0341 (10)	0.0009 (8)	0.0088 (8)	0.0023 (7)

Geometric parameters (Å, º)

N1—N2	1.320 (2)	C3—C4	1.386 (3)
N1—C1	1.332 (2)	C4—C5	1.384 (3)
N2—N3	1.329 (2)	C5—H5	0.9300
N2—C2	1.469 (2)	C5—C6	1.381 (3)
N3—N4	1.317 (2)	C6—H6	0.9300
N4—C1	1.353 (2)	C6—C7	1.386 (3)
N5—C3	1.340 (2)	C7—H7	0.9300
N5—C7	1.338 (2)	C8—H8	0.9300
N6—C8	1.334 (2)	C8—C9	1.384 (3)
N6—C12	1.343 (3)	C9—H9	0.9300
C1—C10	1.470 (2)	C9—C10	1.391 (3)
C2—H2A	0.9700	C10—C11	1.388 (3)
C2—H2B	0.9700	C11—H11	0.9300
C2—C4	1.507 (3)	C11—C12	1.384 (3)
C3—H3	0.9300	C12—H12	0.9300
N2—N1—C1	101.32 (14)	C6—C5—C4	119.22 (18)
N1—N2—N3	114.38 (15)	C6—C5—H5	120.4
N1—N2—C2	122.97 (15)	C5—C6—H6	120.8
N3—N2—C2	122.43 (15)	C5—C6—C7	118.43 (18)
N4—N3—N2	105.80 (14)	C7—C6—H6	120.8
N3—N4—C1	105.97 (15)	N5—C7—C6	123.85 (18)
C7—N5—C3	116.31 (17)	N5—C7—H7	118.1
C8—N6—C12	116.22 (16)	C6—C7—H7	118.1
N1—C1—N4	112.53 (16)	N6—C8—H8	117.8
N1—C1—C10	123.62 (16)	N6—C8—C9	124.37 (18)
N4—C1—C10	123.84 (17)	C9—C8—H8	117.8
N2—C2—H2A	109.5	C8—C9—H9	120.8
N2—C2—H2B	109.5	C8—C9—C10	118.42 (18)
N2—C2—C4	110.83 (15)	C10—C9—H9	120.8
H2A—C2—H2B	108.1	C9—C10—C1	120.22 (17)
C4—C2—H2A	109.5	C11—C10—C1	121.43 (17)
C4—C2—H2B	109.5	C11—C10—C9	118.35 (17)
N5—C3—H3	117.8	C10—C11—H11	120.8
N5—C3—C4	124.39 (17)	C12—C11—C10	118.50 (18)
C4—C3—H3	117.8	C12—C11—H11	120.8
C3—C4—C2	120.37 (17)	N6—C12—C11	124.13 (18)
C5—C4—C2	121.82 (17)	N6—C12—H12	117.9
C5—C4—C3	117.80 (17)	C11—C12—H12	117.9
C4—C5—H5	120.4
N1—N2—N3—N4	−0.41 (19)	C1—N1—N2—N3	0.37 (18)
N1—N2—C2—C4	57.6 (2)	C1—N1—N2—C2	175.20 (15)
N1—C1—C10—C9	178.52 (16)	C1—C10—C11—C12	−179.98 (16)
N1—C1—C10—C11	−1.3 (2)	C2—N2—N3—N4	−175.27 (15)
N2—N1—C1—N4	−0.20 (18)	C2—C4—C5—C6	178.03 (18)
N2—N1—C1—C10	−179.38 (15)	C3—N5—C7—C6	−0.1 (3)
N2—N3—N4—C1	0.24 (18)	C3—C4—C5—C6	−0.8 (3)
N2—C2—C4—C3	99.1 (2)	C4—C5—C6—C7	0.4 (3)
N2—C2—C4—C5	−79.7 (2)	C5—C6—C7—N5	0.1 (3)
N3—N2—C2—C4	−127.97 (17)	C7—N5—C3—C4	−0.4 (3)
N3—N4—C1—N1	−0.03 (19)	C8—N6—C12—C11	0.2 (3)
N3—N4—C1—C10	179.15 (15)	C8—C9—C10—C1	−179.39 (16)
N4—C1—C10—C9	−0.6 (2)	C8—C9—C10—C11	0.4 (2)
N4—C1—C10—C11	179.65 (15)	C9—C10—C11—C12	0.2 (2)
N5—C3—C4—C2	−178.04 (18)	C10—C11—C12—N6	−0.6 (3)
N5—C3—C4—C5	0.8 (3)	C12—N6—C8—C9	0.5 (3)
N6—C8—C9—C10	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N5^i^i	0.97	2.53	3.4312 (2)	154

Symmetry code: (i) −x, y−1/2, −z+1/2.

Bis(µ-4-{2-[(pyridin-3-yl)methyl]-2H-tetrazol-5-yl}pyridine)bis[dichloridozinc(II)] dichloromethane disolvate (I)

Crystal data

[Zn2Cl4(C12H10N6)2]·2CH2Cl2	F(000) = 1840
Mr = 918.95	Dx = 1.640 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.503 (4) Å	Cell parameters from 4389 reflections
b = 8.8791 (11) Å	θ = 2.7–26.1°
c = 15.4063 (17) Å	µ = 1.90 mm^−1
β = 116.856 (5)°	T = 298 K
V = 3722.6 (8) Å^3	Block, colorless
Z = 4	0.42 × 0.40 × 0.35 mm

Data collection

Bruker APEXII CCD area detector diffractometer	2797 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 26.0°, θmin = 2.4°
Tmin = 0.502, Tmax = 0.556	h = −27→37
9723 measured reflections	k = −10→10
3651 independent reflections	l = −17→18

Refinement

Refinement on F^2	46 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.083P)^2 + 1.8947P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
3651 reflections	Δρmax = 0.60 e Å^−3
238 parameters	Δρmin = −0.73 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.15984 (2)	0.60993 (5)	1.09252 (3)	0.05223 (18)
Cl1	0.19387 (4)	0.67519 (14)	1.24811 (7)	0.0725 (3)
Cl2	0.17147 (4)	0.38430 (11)	1.04512 (9)	0.0696 (3)
Cl3	0.04395 (18)	0.7275 (5)	0.2867 (3)	0.1468 (13)	0.556 (3)
Cl4	0.0715 (4)	1.0431 (10)	0.3263 (5)	0.152 (3)	0.556 (3)
Cl5	0.0842 (12)	0.607 (3)	0.292 (2)	0.1468 (13)	0.094 (2)
Cl6	0.0681 (9)	0.882 (3)	0.3657 (19)	0.152 (3)	0.094 (2)
Cl7	0.0795 (4)	0.6823 (9)	0.2913 (5)	0.1468 (13)	0.350 (3)
Cl8	0.0710 (7)	1.0025 (15)	0.2920 (10)	0.152 (3)	0.350 (3)
N1	0.10121 (10)	0.6991 (3)	0.6853 (2)	0.0475 (7)
N2	0.13986 (9)	0.7842 (3)	0.70096 (19)	0.0459 (6)
N3	0.13038 (11)	0.8960 (4)	0.6399 (2)	0.0593 (8)
N4	0.08350 (11)	0.8871 (4)	0.5796 (2)	0.0615 (8)
N5	0.18162 (9)	0.7612 (3)	1.01785 (19)	0.0455 (6)
N6	0.08523 (10)	0.6483 (4)	1.0302 (2)	0.0511 (7)
C1	0.06636 (12)	0.7679 (4)	0.6083 (2)	0.0468 (8)
C2	0.18926 (12)	0.7559 (5)	0.7814 (2)	0.0521 (8)
H2A	0.213730	0.805437	0.767525	0.063*
H2B	0.195941	0.648555	0.786534	0.063*
C3	0.18025 (11)	0.7193 (4)	0.9326 (2)	0.0450 (7)
H3	0.170119	0.621891	0.910541	0.054*
C4	0.19303 (10)	0.8131 (4)	0.8761 (2)	0.0425 (7)
C5	0.20850 (12)	0.9571 (4)	0.9100 (3)	0.0530 (8)
H5	0.217544	1.023441	0.874179	0.064*
C6	0.21038 (14)	1.0015 (4)	0.9977 (3)	0.0577 (9)
H6	0.221149	1.097726	1.021801	0.069*
C7	0.19633 (13)	0.9033 (4)	1.0487 (3)	0.0528 (9)
H7	0.196909	0.935329	1.106697	0.063*
C8	0.05366 (14)	0.5806 (5)	0.9473 (3)	0.0671 (11)
H8	0.065775	0.507854	0.920335	0.081*
C9	0.00434 (14)	0.6137 (5)	0.9006 (3)	0.0638 (10)
H9	−0.016271	0.564257	0.843321	0.077*
C10	−0.01428 (12)	0.7217 (4)	0.9400 (2)	0.0464 (7)
C11	0.01789 (13)	0.7901 (5)	1.0251 (3)	0.0619 (10)
H11	0.006775	0.863114	1.053700	0.074*
C12	0.06728 (13)	0.7491 (5)	1.0681 (3)	0.0614 (10)
H12	0.088527	0.795006	1.126313	0.074*
C13	0.0915 (5)	0.8530 (12)	0.3323 (12)	0.145 (4)	0.556 (3)
H13A	0.110443	0.844025	0.296156	0.173*	0.556 (3)
H13B	0.112963	0.827536	0.399605	0.173*	0.556 (3)
C14	0.1059 (11)	0.786 (3)	0.3296 (11)	0.145 (4)	0.094 (2)
H14A	0.107846	0.839631	0.276627	0.173*	0.094 (2)
H14B	0.138717	0.780568	0.383325	0.173*	0.094 (2)
C15	0.0919 (11)	0.8396 (16)	0.3615 (12)	0.145 (4)	0.350 (3)
H15A	0.127073	0.847231	0.401952	0.173*	0.350 (3)
H15B	0.076385	0.830798	0.404131	0.173*	0.350 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0377 (2)	0.0631 (3)	0.0513 (3)	0.00366 (17)	0.01604 (19)	0.00728 (18)
Cl1	0.0617 (6)	0.0914 (8)	0.0505 (5)	−0.0037 (5)	0.0131 (4)	0.0021 (5)
Cl2	0.0695 (6)	0.0570 (6)	0.0893 (7)	0.0068 (4)	0.0419 (6)	0.0081 (5)
Cl3	0.146 (3)	0.149 (3)	0.1191 (17)	−0.017 (3)	0.037 (2)	0.0147 (19)
Cl4	0.1043 (16)	0.163 (5)	0.147 (6)	−0.027 (3)	0.019 (4)	0.039 (4)
Cl5	0.146 (3)	0.149 (3)	0.1191 (17)	−0.017 (3)	0.037 (2)	0.0147 (19)
Cl6	0.1043 (16)	0.163 (5)	0.147 (6)	−0.027 (3)	0.019 (4)	0.039 (4)
Cl7	0.146 (3)	0.149 (3)	0.1191 (17)	−0.017 (3)	0.037 (2)	0.0147 (19)
Cl8	0.1043 (16)	0.163 (5)	0.147 (6)	−0.027 (3)	0.019 (4)	0.039 (4)
N1	0.0374 (14)	0.0558 (17)	0.0460 (15)	−0.0016 (12)	0.0160 (12)	0.0038 (13)
N2	0.0338 (14)	0.0583 (17)	0.0430 (14)	−0.0028 (12)	0.0150 (11)	0.0006 (13)
N3	0.0465 (17)	0.062 (2)	0.0601 (18)	−0.0075 (14)	0.0163 (14)	0.0093 (15)
N4	0.0448 (17)	0.062 (2)	0.0619 (19)	−0.0036 (14)	0.0102 (14)	0.0162 (15)
N5	0.0364 (14)	0.0494 (16)	0.0483 (15)	0.0049 (11)	0.0170 (12)	−0.0001 (12)
N6	0.0371 (14)	0.0561 (17)	0.0535 (16)	0.0000 (12)	0.0148 (13)	0.0011 (14)
C1	0.0386 (17)	0.0509 (19)	0.0471 (17)	0.0012 (14)	0.0161 (14)	0.0010 (15)
C2	0.0311 (16)	0.071 (2)	0.0501 (18)	0.0056 (15)	0.0145 (14)	0.0031 (17)
C3	0.0327 (15)	0.0422 (17)	0.0527 (19)	−0.0002 (13)	0.0128 (14)	−0.0039 (14)
C4	0.0275 (14)	0.0472 (18)	0.0459 (17)	0.0041 (12)	0.0105 (13)	0.0016 (14)
C5	0.0424 (18)	0.0501 (19)	0.063 (2)	−0.0016 (15)	0.0205 (16)	0.0069 (17)
C6	0.053 (2)	0.0404 (19)	0.071 (2)	0.0002 (15)	0.0208 (18)	−0.0089 (17)
C7	0.0452 (18)	0.056 (2)	0.054 (2)	0.0080 (15)	0.0192 (16)	−0.0100 (16)
C8	0.048 (2)	0.083 (3)	0.065 (2)	0.0096 (19)	0.0204 (18)	−0.014 (2)
C9	0.0421 (19)	0.079 (3)	0.057 (2)	0.0034 (18)	0.0097 (16)	−0.0160 (19)
C10	0.0387 (16)	0.0509 (19)	0.0446 (17)	−0.0019 (14)	0.0143 (14)	0.0010 (14)
C11	0.045 (2)	0.068 (2)	0.062 (2)	0.0081 (17)	0.0141 (17)	−0.0130 (19)
C12	0.0396 (19)	0.068 (2)	0.059 (2)	0.0002 (17)	0.0071 (16)	−0.0101 (19)
C13	0.113 (5)	0.150 (6)	0.140 (6)	−0.025 (5)	0.032 (5)	0.042 (5)
C14	0.113 (5)	0.150 (6)	0.140 (6)	−0.025 (5)	0.032 (5)	0.042 (5)
C15	0.113 (5)	0.150 (6)	0.140 (6)	−0.025 (5)	0.032 (5)	0.042 (5)

Geometric parameters (Å, º)

Zn1—N6	2.060 (3)	C2—H2B	0.9700
Zn1—N5	2.064 (3)	C3—C4	1.381 (5)
Zn1—Cl2	2.2151 (12)	C3—H3	0.9300
Zn1—Cl1	2.2161 (11)	C4—C5	1.381 (5)
Cl3—C13	1.708 (10)	C5—C6	1.385 (5)
Cl3—Cl3^i	2.393 (10)	C5—H5	0.9300
Cl4—C13	1.783 (9)	C6—C7	1.366 (5)
Cl5—C14	1.716 (10)	C6—H6	0.9300
Cl6—C14	1.716 (10)	C7—H7	0.9300
Cl7—C15	1.701 (10)	C8—C9	1.375 (5)
Cl8—C15	1.740 (10)	C8—H8	0.9300
N1—N2	1.327 (4)	C9—C10	1.387 (5)
N1—C1	1.331 (4)	C9—H9	0.9300
N2—N3	1.308 (4)	C10—C11	1.374 (5)
N2—C2	1.477 (4)	C11—C12	1.392 (5)
N3—N4	1.309 (4)	C11—H11	0.9300
N4—C1	1.341 (5)	C12—H12	0.9300
N5—C3	1.347 (4)	C13—H13A	0.9700
N5—C7	1.351 (4)	C13—H13B	0.9700
N6—C12	1.315 (5)	C14—H14A	0.9700
N6—C8	1.345 (5)	C14—H14B	0.9700
C1—C10^ii	1.475 (5)	C15—H15A	0.9700
C2—C4	1.500 (5)	C15—H15B	0.9700
C2—H2A	0.9700
N6—Zn1—N5	101.47 (11)	C7—C6—H6	120.2
N6—Zn1—Cl2	107.69 (9)	C5—C6—H6	120.2
N5—Zn1—Cl2	105.37 (8)	N5—C7—C6	122.3 (3)
N6—Zn1—Cl1	109.86 (9)	N5—C7—H7	118.9
N5—Zn1—Cl1	108.74 (8)	C6—C7—H7	118.9
Cl2—Zn1—Cl1	121.77 (5)	N6—C8—C9	123.1 (4)
C13—Cl3—Cl3^i	139.1 (5)	N6—C8—H8	118.4
N2—N1—C1	100.8 (3)	C9—C8—H8	118.4
N3—N2—N1	114.3 (3)	C8—C9—C10	119.1 (3)
N3—N2—C2	122.9 (3)	C8—C9—H9	120.4
N1—N2—C2	122.8 (3)	C10—C9—H9	120.4
N2—N3—N4	106.3 (3)	C11—C10—C9	117.8 (3)
N3—N4—C1	106.1 (3)	C11—C10—C1^ii	120.0 (3)
C3—N5—C7	117.4 (3)	C9—C10—C1^ii	122.2 (3)
C3—N5—Zn1	119.2 (2)	C10—C11—C12	119.4 (4)
C7—N5—Zn1	123.4 (2)	C10—C11—H11	120.3
C12—N6—C8	117.6 (3)	C12—C11—H11	120.3
C12—N6—Zn1	120.0 (2)	N6—C12—C11	123.0 (3)
C8—N6—Zn1	122.3 (3)	N6—C12—H12	118.5
N1—C1—N4	112.5 (3)	C11—C12—H12	118.5
N1—C1—C10^ii	124.5 (3)	Cl3—C13—Cl4	112.9 (8)
N4—C1—C10^ii	123.0 (3)	Cl3—C13—H13A	109.0
N2—C2—C4	111.1 (3)	Cl4—C13—H13A	109.0
N2—C2—H2A	109.4	Cl3—C13—H13B	109.0
C4—C2—H2A	109.4	Cl4—C13—H13B	109.0
N2—C2—H2B	109.4	H13A—C13—H13B	107.8
C4—C2—H2B	109.4	Cl5—C14—Cl6	110.8 (13)
H2A—C2—H2B	108.0	Cl5—C14—H14A	109.5
N5—C3—C4	123.7 (3)	Cl6—C14—H14A	109.5
N5—C3—H3	118.2	Cl5—C14—H14B	109.5
C4—C3—H3	118.2	Cl6—C14—H14B	109.5
C5—C4—C3	117.8 (3)	H14A—C14—H14B	108.1
C5—C4—C2	122.9 (3)	Cl7—C15—Cl8	112.1 (10)
C3—C4—C2	119.3 (3)	Cl7—C15—H15A	109.2
C4—C5—C6	119.3 (3)	Cl8—C15—H15A	109.2
C4—C5—H5	120.4	Cl7—C15—H15B	109.2
C6—C5—H5	120.4	Cl8—C15—H15B	109.2
C7—C6—C5	119.6 (3)	H15A—C15—H15B	107.9
C1—N1—N2—N3	0.1 (4)	C3—C4—C5—C6	−0.2 (5)
C1—N1—N2—C2	179.3 (3)	C2—C4—C5—C6	179.2 (3)
N1—N2—N3—N4	−0.3 (4)	C4—C5—C6—C7	−0.9 (5)
C2—N2—N3—N4	−179.6 (3)	C3—N5—C7—C6	−1.3 (5)
N2—N3—N4—C1	0.4 (4)	Zn1—N5—C7—C6	−179.7 (3)
N2—N1—C1—N4	0.2 (4)	C5—C6—C7—N5	1.7 (5)
N2—N1—C1—C10^ii	−178.6 (3)	C12—N6—C8—C9	1.1 (7)
N3—N4—C1—N1	−0.4 (4)	Zn1—N6—C8—C9	−174.6 (3)
N3—N4—C1—C10^ii	178.4 (3)	N6—C8—C9—C10	0.0 (7)
N3—N2—C2—C4	100.5 (4)	C8—C9—C10—C11	−0.5 (6)
N1—N2—C2—C4	−78.7 (4)	C8—C9—C10—C1^ii	177.3 (4)
C7—N5—C3—C4	0.1 (5)	C9—C10—C11—C12	0.0 (6)
Zn1—N5—C3—C4	178.6 (2)	C1^ii—C10—C11—C12	−177.9 (4)
N5—C3—C4—C5	0.6 (5)	C8—N6—C12—C11	−1.6 (6)
N5—C3—C4—C2	−178.9 (3)	Zn1—N6—C12—C11	174.2 (3)
N2—C2—C4—C5	−90.6 (4)	C10—C11—C12—N6	1.1 (7)
N2—C2—C4—C3	88.9 (4)	Cl3^i—Cl3—C13—Cl4	0.9 (17)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl2^i^iii	0.93	3.06	3.7784 (4)	135
C8—H8···Cl5^ii^iv	0.93	2.50	3.3699 (3)	156
C7—C7···N3^iii^v	0.93	2.75	3.4272 (3)	131

Symmetry codes: (iii) x, y+1, z; (iv) x, −y+1, z+1/2; (v) x, −y+2, z+1/2.

Bis(µ-4-{2-[(pyridin-3-yl)methyl]-2H-tetrazol-5-yl}pyridine)bis[dichloridozinc(II)] chloroform monosolvate (II)

Crystal data

[Zn2Cl4(C12H10N6)2]·CHCl3	F(000) = 1736
Mr = 1736.85	Dx = 1.646 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.414 (9) Å	Cell parameters from 6740 reflections
b = 18.504 (12) Å	θ = 2.9–26.0°
c = 14.674 (10) Å	µ = 1.94 mm^−1
β = 105.834 (9)°	T = 298 K
V = 3504 (4) Å^3	Block, colorless
Z = 2	0.45 × 0.43 × 0.42 mm

Data collection

Bruker APEXII CCD area detector diffractometer	4796 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 26.0°, θmin = 1.8°
Tmin = 0.475, Tmax = 0.496	h = −16→13
15365 measured reflections	k = −22→18
6801 independent reflections	l = −18→17

Refinement

Refinement on F^2	48 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0522P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.001
6801 reflections	Δρmax = 0.63 e Å^−3
428 parameters	Δρmin = −0.42 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.76458 (3)	0.14536 (2)	0.40041 (2)	0.04483 (11)
Zn2	−0.04809 (3)	−0.06927 (2)	0.18912 (2)	0.04574 (12)
Cl1	0.83857 (7)	0.05257 (5)	0.48696 (6)	0.0629 (2)
Cl2	0.83982 (7)	0.25138 (5)	0.41435 (7)	0.0695 (3)
Cl3	−0.09499 (7)	−0.13615 (5)	0.29445 (6)	0.0624 (2)
Cl4	−0.13486 (8)	−0.07204 (5)	0.03727 (6)	0.0653 (3)
Cl5	0.39421 (12)	0.07288 (7)	0.15768 (13)	0.1052 (5)	0.9092 (16)
Cl6	0.42649 (12)	0.22301 (8)	0.18609 (11)	0.1121 (5)	0.9092 (16)
Cl7	0.23907 (13)	0.16158 (14)	0.20585 (13)	0.1507 (9)	0.9092 (16)
Cl5'	0.2447 (10)	0.0856 (7)	0.2431 (11)	0.1052 (5)	0.0908 (16)
Cl6'	0.3252 (13)	0.2206 (6)	0.2014 (11)	0.1121 (5)	0.0908 (16)
Cl7'	0.4348 (13)	0.0913 (11)	0.2037 (15)	0.1507 (9)	0.0908 (16)
N1	0.4692 (2)	−0.09165 (13)	0.15673 (17)	0.0453 (6)
N2	0.56888 (19)	−0.10271 (13)	0.19884 (17)	0.0442 (6)
N3	0.5871 (2)	−0.12909 (17)	0.2849 (2)	0.0659 (8)
N4	0.4954 (2)	−0.13626 (18)	0.3009 (2)	0.0689 (9)
N5	0.71654 (19)	0.10477 (13)	0.26477 (16)	0.0448 (6)
N6	0.1052 (2)	−0.08985 (14)	0.19876 (17)	0.0455 (6)
N7	0.2569 (2)	0.13377 (13)	0.45862 (18)	0.0481 (6)
N8	0.17711 (19)	0.16731 (14)	0.47548 (17)	0.0459 (6)
N9	0.1951 (2)	0.23542 (15)	0.4981 (2)	0.0657 (8)
N10	0.2912 (2)	0.24820 (16)	0.4960 (2)	0.0662 (8)
N11	−0.03741 (19)	0.03711 (13)	0.23140 (16)	0.0444 (6)
N12	0.6238 (2)	0.15958 (14)	0.42838 (18)	0.0479 (6)
C1	0.4257 (2)	−0.11253 (16)	0.2232 (2)	0.0434 (7)
C2	0.6515 (2)	−0.07982 (16)	0.1572 (2)	0.0471 (8)
H2A	0.634095	−0.093967	0.091031	0.057*
H2B	0.715907	−0.103375	0.189841	0.057*
C3	0.7071 (2)	0.03275 (16)	0.2518 (2)	0.0430 (7)
H3	0.730507	0.002834	0.304227	0.052*
C4	0.6649 (2)	0.00128 (16)	0.1652 (2)	0.0416 (7)
C5	0.6327 (3)	0.04588 (19)	0.0882 (2)	0.0541 (8)
H5	0.604211	0.026278	0.028358	0.065*
C6	0.6423 (3)	0.1194 (2)	0.0992 (2)	0.0605 (9)
H6	0.621160	0.149953	0.047125	0.073*
C7	0.6838 (3)	0.14733 (17)	0.1883 (2)	0.0535 (8)
H7	0.689360	0.197199	0.195875	0.064*
C8	0.1715 (3)	−0.1104 (2)	0.2802 (2)	0.0599 (9)
H8	0.146138	−0.119355	0.332127	0.072*
C9	0.2755 (3)	−0.1189 (2)	0.2902 (2)	0.0596 (9)
H9	0.319710	−0.132545	0.348233	0.072*
C10	0.3141 (2)	−0.10707 (16)	0.2135 (2)	0.0438 (7)
C11	0.2454 (3)	−0.0865 (2)	0.1298 (2)	0.0581 (9)
H11	0.268307	−0.078334	0.076307	0.070*
C12	0.1436 (3)	−0.07826 (19)	0.1257 (2)	0.0575 (9)
H12	0.098369	−0.063702	0.068599	0.069*
C13	0.3270 (2)	0.18549 (17)	0.4721 (2)	0.0442 (7)
C14	0.0752 (2)	0.13415 (17)	0.4613 (2)	0.0469 (8)
H14A	0.031076	0.165753	0.486070	0.056*
H14B	0.082115	0.088720	0.495464	0.056*
C15	0.0049 (2)	0.05221 (16)	0.3236 (2)	0.0421 (7)
H15	0.020355	0.014009	0.366299	0.050*
C16	0.0265 (2)	0.12095 (16)	0.3576 (2)	0.0411 (7)
C17	0.0018 (3)	0.17749 (18)	0.2936 (2)	0.0550 (8)
H17	0.015166	0.224915	0.314294	0.066*
C18	−0.0428 (3)	0.16316 (19)	0.1990 (2)	0.0623 (10)
H18	−0.060116	0.200606	0.155262	0.075*
C19	−0.0612 (3)	0.0927 (2)	0.1707 (2)	0.0560 (9)
H19	−0.091406	0.083075	0.106920	0.067*
C20	0.5891 (3)	0.22412 (18)	0.4433 (2)	0.0543 (8)
H20	0.631022	0.264065	0.442610	0.065*
C21	0.4937 (3)	0.23511 (17)	0.4597 (2)	0.0549 (9)
H21	0.472561	0.281378	0.470815	0.066*
C22	0.4303 (2)	0.17673 (17)	0.4595 (2)	0.0458 (7)
C23	0.4666 (3)	0.10914 (19)	0.4444 (3)	0.0634 (10)
H23	0.426157	0.068333	0.444446	0.076*
C24	0.5627 (3)	0.10267 (19)	0.4293 (3)	0.0647 (10)
H24	0.586271	0.056877	0.419261	0.078*
C25	0.3329 (3)	0.1567 (2)	0.1465 (3)	0.0812 (14)	0.9092 (16)
H25	0.299781	0.165188	0.079074	0.097*	0.9092 (16)
C25'	0.3132 (15)	0.1296 (8)	0.1760 (17)	0.0812 (14)	0.0908 (16)
H25'	0.278858	0.122654	0.108546	0.097*	0.0908 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0427 (2)	0.0410 (2)	0.0494 (2)	0.00221 (16)	0.01019 (16)	−0.00008 (15)
Zn2	0.0410 (2)	0.0521 (2)	0.0431 (2)	−0.00295 (17)	0.00976 (16)	−0.00350 (15)
Cl1	0.0735 (6)	0.0551 (5)	0.0528 (5)	0.0150 (4)	0.0049 (4)	0.0087 (4)
Cl2	0.0627 (6)	0.0434 (5)	0.1057 (7)	−0.0055 (4)	0.0286 (5)	−0.0042 (5)
Cl3	0.0517 (5)	0.0778 (6)	0.0581 (5)	−0.0018 (4)	0.0158 (4)	0.0159 (4)
Cl4	0.0693 (6)	0.0727 (6)	0.0442 (4)	−0.0110 (5)	−0.0008 (4)	−0.0025 (4)
Cl5	0.0929 (10)	0.0717 (9)	0.1375 (13)	0.0035 (7)	0.0086 (9)	−0.0045 (8)
Cl6	0.1087 (12)	0.0798 (9)	0.1341 (12)	−0.0089 (8)	0.0099 (10)	−0.0238 (8)
Cl7	0.0956 (12)	0.240 (3)	0.1264 (13)	−0.0155 (13)	0.0464 (10)	−0.0610 (14)
Cl5'	0.0929 (10)	0.0717 (9)	0.1375 (13)	0.0035 (7)	0.0086 (9)	−0.0045 (8)
Cl6'	0.1087 (12)	0.0798 (9)	0.1341 (12)	−0.0089 (8)	0.0099 (10)	−0.0238 (8)
Cl7'	0.0956 (12)	0.240 (3)	0.1264 (13)	−0.0155 (13)	0.0464 (10)	−0.0610 (14)
N1	0.0378 (15)	0.0469 (15)	0.0500 (14)	0.0001 (12)	0.0098 (12)	0.0000 (12)
N2	0.0391 (16)	0.0409 (15)	0.0526 (15)	−0.0011 (12)	0.0124 (12)	0.0000 (12)
N3	0.0512 (19)	0.085 (2)	0.0589 (18)	0.0051 (16)	0.0107 (15)	0.0219 (16)
N4	0.0527 (19)	0.096 (3)	0.0582 (18)	0.0041 (17)	0.0162 (15)	0.0258 (16)
N5	0.0441 (16)	0.0409 (15)	0.0472 (14)	−0.0021 (12)	0.0087 (12)	0.0013 (11)
N6	0.0428 (15)	0.0505 (16)	0.0438 (14)	−0.0024 (12)	0.0126 (12)	−0.0001 (11)
N7	0.0433 (16)	0.0451 (16)	0.0570 (16)	0.0028 (13)	0.0155 (13)	−0.0073 (12)
N8	0.0409 (16)	0.0470 (16)	0.0496 (14)	0.0002 (12)	0.0120 (12)	−0.0099 (12)
N9	0.053 (2)	0.0492 (18)	0.099 (2)	−0.0051 (14)	0.0266 (17)	−0.0278 (16)
N10	0.052 (2)	0.0544 (19)	0.095 (2)	−0.0074 (15)	0.0241 (17)	−0.0252 (16)
N11	0.0431 (15)	0.0484 (16)	0.0399 (13)	0.0016 (12)	0.0083 (12)	0.0002 (11)
N12	0.0425 (16)	0.0416 (16)	0.0591 (16)	0.0001 (12)	0.0130 (13)	−0.0011 (12)
C1	0.0418 (19)	0.0462 (18)	0.0423 (16)	−0.0023 (15)	0.0116 (15)	0.0026 (13)
C2	0.0403 (18)	0.0466 (19)	0.0565 (18)	0.0011 (14)	0.0168 (15)	−0.0060 (14)
C3	0.0410 (18)	0.0436 (18)	0.0439 (16)	0.0019 (14)	0.0107 (14)	0.0047 (13)
C4	0.0336 (16)	0.0466 (18)	0.0474 (17)	−0.0013 (14)	0.0159 (14)	−0.0005 (14)
C5	0.056 (2)	0.062 (2)	0.0436 (17)	−0.0111 (17)	0.0118 (16)	0.0031 (15)
C6	0.067 (2)	0.059 (2)	0.0495 (19)	−0.0115 (19)	0.0058 (17)	0.0189 (16)
C7	0.055 (2)	0.0432 (19)	0.061 (2)	−0.0045 (16)	0.0142 (17)	0.0085 (16)
C8	0.055 (2)	0.078 (3)	0.052 (2)	−0.0001 (19)	0.0231 (18)	0.0074 (18)
C9	0.048 (2)	0.081 (3)	0.0477 (18)	0.0017 (19)	0.0100 (16)	0.0126 (17)
C10	0.0429 (19)	0.0402 (17)	0.0497 (18)	−0.0065 (14)	0.0149 (15)	−0.0011 (14)
C11	0.044 (2)	0.088 (3)	0.0456 (18)	−0.0029 (18)	0.0178 (16)	0.0051 (17)
C12	0.047 (2)	0.082 (3)	0.0430 (18)	−0.0033 (18)	0.0112 (16)	0.0052 (16)
C13	0.0412 (18)	0.0426 (18)	0.0474 (17)	−0.0009 (15)	0.0097 (14)	−0.0070 (13)
C14	0.0428 (19)	0.051 (2)	0.0475 (17)	−0.0006 (15)	0.0127 (15)	−0.0047 (14)
C15	0.0391 (17)	0.0457 (18)	0.0405 (16)	0.0030 (14)	0.0094 (13)	0.0043 (13)
C16	0.0349 (17)	0.0430 (18)	0.0464 (17)	0.0026 (14)	0.0125 (14)	−0.0024 (13)
C17	0.061 (2)	0.0453 (19)	0.059 (2)	0.0019 (17)	0.0161 (17)	0.0025 (15)
C18	0.075 (3)	0.056 (2)	0.052 (2)	0.0085 (19)	0.0107 (18)	0.0163 (16)
C19	0.057 (2)	0.065 (2)	0.0429 (18)	0.0041 (17)	0.0072 (16)	0.0055 (16)
C20	0.046 (2)	0.048 (2)	0.069 (2)	−0.0047 (16)	0.0160 (17)	−0.0013 (16)
C21	0.058 (2)	0.0398 (19)	0.067 (2)	0.0040 (16)	0.0171 (18)	−0.0080 (15)
C22	0.046 (2)	0.0456 (18)	0.0441 (16)	−0.0006 (15)	0.0094 (15)	−0.0044 (13)
C23	0.055 (2)	0.045 (2)	0.095 (3)	−0.0063 (17)	0.029 (2)	−0.0046 (18)
C24	0.058 (2)	0.043 (2)	0.098 (3)	0.0040 (18)	0.031 (2)	−0.0043 (19)
C25	0.077 (3)	0.089 (4)	0.070 (3)	0.005 (3)	0.005 (2)	−0.015 (2)
C25'	0.077 (3)	0.089 (4)	0.070 (3)	0.005 (3)	0.005 (2)	−0.015 (2)

Geometric parameters (Å, º)

Zn1—N12	2.056 (3)	C3—C4	1.372 (4)
Zn1—N5	2.059 (3)	C3—H3	0.9300
Zn1—Cl2	2.1902 (15)	C4—C5	1.370 (4)
Zn1—Cl1	2.2041 (13)	C5—C6	1.373 (5)
Zn2—N11	2.057 (3)	C5—H5	0.9300
Zn2—N6	2.058 (3)	C6—C7	1.374 (5)
Zn2—Cl3	2.2016 (13)	C6—H6	0.9300
Zn2—Cl4	2.2152 (15)	C7—H7	0.9300
Cl5—C25	1.742 (4)	C8—C9	1.372 (5)
Cl6—C25	1.739 (4)	C8—H8	0.9300
Cl7—C25	1.717 (5)	C9—C10	1.378 (4)
Cl5'—C25'	1.724 (10)	C9—H9	0.9300
Cl6'—C25'	1.722 (10)	C10—C11	1.373 (4)
Cl7'—C25'	1.723 (10)	C11—C12	1.359 (5)
N1—C1	1.324 (4)	C11—H11	0.9300
N1—N2	1.327 (3)	C12—H12	0.9300
N2—N3	1.314 (4)	C13—C22	1.457 (4)
N2—C2	1.467 (4)	C14—C16	1.504 (4)
N3—N4	1.320 (4)	C14—H14A	0.9700
N4—C1	1.336 (4)	C14—H14B	0.9700
N5—C7	1.343 (4)	C15—C16	1.368 (4)
N5—C3	1.347 (4)	C15—H15	0.9300
N6—C12	1.327 (4)	C16—C17	1.384 (4)
N6—C8	1.336 (4)	C17—C18	1.379 (5)
N7—N8	1.317 (3)	C17—H17	0.9300
N7—C13	1.318 (4)	C18—C19	1.370 (5)
N8—N9	1.309 (4)	C18—H18	0.9300
N8—C14	1.461 (4)	C19—H19	0.9300
N9—N10	1.318 (4)	C20—C21	1.382 (5)
N10—C13	1.339 (4)	C20—H20	0.9300
N11—C19	1.341 (4)	C21—C22	1.374 (4)
N11—C15	1.346 (4)	C21—H21	0.9300
N12—C20	1.321 (4)	C22—C23	1.382 (5)
N12—C24	1.337 (4)	C23—C24	1.371 (5)
C1—C10	1.468 (4)	C23—H23	0.9300
C2—C4	1.512 (4)	C24—H24	0.9300
C2—H2A	0.9700	C25—H25	0.9800
C2—H2B	0.9700	C25'—H25'	0.9800
N12—Zn1—N5	100.22 (10)	C8—C9—C10	119.5 (3)
N12—Zn1—Cl2	106.95 (8)	C8—C9—H9	120.3
N5—Zn1—Cl2	115.57 (8)	C10—C9—H9	120.3
N12—Zn1—Cl1	106.17 (8)	C11—C10—C9	117.7 (3)
N5—Zn1—Cl1	104.23 (8)	C11—C10—C1	121.6 (3)
Cl2—Zn1—Cl1	121.36 (5)	C9—C10—C1	120.7 (3)
N11—Zn2—N6	99.80 (10)	C12—C11—C10	119.5 (3)
N11—Zn2—Cl3	109.63 (8)	C12—C11—H11	120.3
N6—Zn2—Cl3	108.63 (8)	C10—C11—H11	120.3
N11—Zn2—Cl4	107.44 (7)	N6—C12—C11	123.5 (3)
N6—Zn2—Cl4	107.80 (8)	N6—C12—H12	118.2
Cl3—Zn2—Cl4	121.39 (5)	C11—C12—H12	118.2
C1—N1—N2	101.7 (2)	N7—C13—N10	112.1 (3)
N3—N2—N1	113.9 (3)	N7—C13—C22	124.4 (3)
N3—N2—C2	123.0 (3)	N10—C13—C22	123.5 (3)
N1—N2—C2	122.8 (3)	N8—C14—C16	110.1 (2)
N2—N3—N4	105.7 (3)	N8—C14—H14A	109.6
N3—N4—C1	106.6 (3)	C16—C14—H14A	109.6
C7—N5—C3	117.7 (3)	N8—C14—H14B	109.6
C7—N5—Zn1	122.6 (2)	C16—C14—H14B	109.6
C3—N5—Zn1	119.33 (19)	H14A—C14—H14B	108.2
C12—N6—C8	117.3 (3)	N11—C15—C16	123.3 (3)
C12—N6—Zn2	121.0 (2)	N11—C15—H15	118.4
C8—N6—Zn2	121.5 (2)	C16—C15—H15	118.4
N8—N7—C13	102.3 (3)	C15—C16—C17	117.9 (3)
N9—N8—N7	113.4 (3)	C15—C16—C14	120.7 (3)
N9—N8—C14	122.8 (3)	C17—C16—C14	121.4 (3)
N7—N8—C14	123.5 (3)	C18—C17—C16	119.7 (3)
N8—N9—N10	106.3 (3)	C18—C17—H17	120.2
N9—N10—C13	105.9 (3)	C16—C17—H17	120.2
C19—N11—C15	117.8 (3)	C19—C18—C17	118.8 (3)
C19—N11—Zn2	123.3 (2)	C19—C18—H18	120.6
C15—N11—Zn2	118.52 (19)	C17—C18—H18	120.6
C20—N12—C24	117.8 (3)	N11—C19—C18	122.6 (3)
C20—N12—Zn1	122.2 (2)	N11—C19—H19	118.7
C24—N12—Zn1	120.0 (2)	C18—C19—H19	118.7
N1—C1—N4	112.2 (3)	N12—C20—C21	123.1 (3)
N1—C1—C10	123.5 (3)	N12—C20—H20	118.4
N4—C1—C10	124.3 (3)	C21—C20—H20	118.4
N2—C2—C4	110.0 (2)	C22—C21—C20	119.1 (3)
N2—C2—H2A	109.7	C22—C21—H21	120.5
C4—C2—H2A	109.7	C20—C21—H21	120.5
N2—C2—H2B	109.7	C21—C22—C23	117.9 (3)
C4—C2—H2B	109.7	C21—C22—C13	121.4 (3)
H2A—C2—H2B	108.2	C23—C22—C13	120.7 (3)
N5—C3—C4	123.3 (3)	C24—C23—C22	119.5 (3)
N5—C3—H3	118.3	C24—C23—H23	120.2
C4—C3—H3	118.3	C22—C23—H23	120.2
C5—C4—C3	117.8 (3)	N12—C24—C23	122.6 (3)
C5—C4—C2	122.0 (3)	N12—C24—H24	118.7
C3—C4—C2	120.2 (3)	C23—C24—H24	118.7
C4—C5—C6	120.1 (3)	Cl7—C25—Cl6	110.8 (2)
C4—C5—H5	119.9	Cl7—C25—Cl5	113.1 (3)
C6—C5—H5	119.9	Cl6—C25—Cl5	108.5 (2)
C5—C6—C7	119.0 (3)	Cl7—C25—H25	108.1
C5—C6—H6	120.5	Cl6—C25—H25	108.1
C7—C6—H6	120.5	Cl5—C25—H25	108.1
N5—C7—C6	122.0 (3)	Cl6'—C25'—Cl7'	109.0 (11)
N5—C7—H7	119.0	Cl6'—C25'—Cl5'	111.8 (11)
C6—C7—H7	119.0	Cl7'—C25'—Cl5'	106.8 (11)
N6—C8—C9	122.5 (3)	Cl6'—C25'—H25'	109.7
N6—C8—H8	118.7	Cl7'—C25'—H25'	109.7
C9—C8—H8	118.7	Cl5'—C25'—H25'	109.7
C1—N1—N2—N3	0.5 (3)	C9—C10—C11—C12	0.4 (5)
C1—N1—N2—C2	−172.9 (3)	C1—C10—C11—C12	−176.3 (3)
N1—N2—N3—N4	0.3 (4)	C8—N6—C12—C11	0.3 (5)
C2—N2—N3—N4	173.6 (3)	Zn2—N6—C12—C11	175.7 (3)
N2—N3—N4—C1	−0.9 (4)	C10—C11—C12—N6	−0.8 (6)
C13—N7—N8—N9	0.0 (3)	N8—N7—C13—N10	−0.2 (3)
C13—N7—N8—C14	174.2 (3)	N8—N7—C13—C22	−178.2 (3)
N7—N8—N9—N10	0.2 (4)	N9—N10—C13—N7	0.3 (4)
C14—N8—N9—N10	−174.1 (3)	N9—N10—C13—C22	178.3 (3)
N8—N9—N10—C13	−0.3 (4)	N9—N8—C14—C16	106.6 (3)
N2—N1—C1—N4	−1.1 (3)	N7—N8—C14—C16	−67.0 (4)
N2—N1—C1—C10	176.4 (3)	C19—N11—C15—C16	−1.3 (5)
N3—N4—C1—N1	1.3 (4)	Zn2—N11—C15—C16	172.4 (2)
N3—N4—C1—C10	−176.2 (3)	N11—C15—C16—C17	1.0 (5)
N3—N2—C2—C4	−98.8 (3)	N11—C15—C16—C14	−179.2 (3)
N1—N2—C2—C4	74.0 (3)	N8—C14—C16—C15	116.7 (3)
C7—N5—C3—C4	−0.9 (5)	N8—C14—C16—C17	−63.5 (4)
Zn1—N5—C3—C4	172.5 (2)	C15—C16—C17—C18	−0.2 (5)
N5—C3—C4—C5	1.3 (5)	C14—C16—C17—C18	−180.0 (3)
N5—C3—C4—C2	−176.6 (3)	C16—C17—C18—C19	−0.3 (5)
N2—C2—C4—C5	−107.0 (3)	C15—N11—C19—C18	0.8 (5)
N2—C2—C4—C3	70.8 (4)	Zn2—N11—C19—C18	−172.5 (3)
C3—C4—C5—C6	−0.6 (5)	C17—C18—C19—N11	−0.1 (6)
C2—C4—C5—C6	177.3 (3)	C24—N12—C20—C21	0.2 (5)
C4—C5—C6—C7	−0.5 (5)	Zn1—N12—C20—C21	178.3 (2)
C3—N5—C7—C6	−0.3 (5)	N12—C20—C21—C22	−1.0 (5)
Zn1—N5—C7—C6	−173.4 (3)	C20—C21—C22—C23	1.2 (5)
C5—C6—C7—N5	1.0 (5)	C20—C21—C22—C13	−177.1 (3)
C12—N6—C8—C9	0.7 (5)	N7—C13—C22—C21	169.4 (3)
Zn2—N6—C8—C9	−174.7 (3)	N10—C13—C22—C21	−8.4 (5)
N6—C8—C9—C10	−1.1 (6)	N7—C13—C22—C23	−8.9 (5)
C8—C9—C10—C11	0.5 (5)	N10—C13—C22—C23	173.3 (3)
C8—C9—C10—C1	177.2 (3)	C21—C22—C23—C24	−0.7 (5)
N1—C1—C10—C11	6.9 (5)	C13—C22—C23—C24	177.6 (3)
N4—C1—C10—C11	−175.9 (3)	C20—N12—C24—C23	0.4 (5)
N1—C1—C10—C9	−169.7 (3)	Zn1—N12—C24—C23	−177.8 (3)
N4—C1—C10—C9	7.5 (5)	C22—C23—C24—N12	−0.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cl2^i^i	0.97	2.89	3.307 (4)	107
C14—H14B···Cl1^ii^ii	0.97	2.81	3.657 (4)	147

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y, −z+1.

Bis(µ-4-{2-[(pyridin-3-yl)methyl]-2H-tetrazol-5-yl}pyridine)bis[diiodidozinc(II)] dichloromethane disolvate (III)

Crystal data

[Zn2I4(C12H10N6)2]·2CH2Cl2	F(000) = 2416
Mr = 1284.71	Dx = 2.121 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.312 (10) Å	Cell parameters from 4761 reflections
b = 9.461 (3) Å	θ = 2.5–26.7°
c = 15.434 (5) Å	µ = 4.56 mm^−1
β = 114.625 (4)°	T = 298 K
V = 4024 (2) Å^3	Block, colorless
Z = 4	0.40 × 0.36 × 0.35 mm

Data collection

Bruker APEXII CCD area detector diffractometer	3027 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 26.0°, θmin = 2.3°
Tmin = 0.263, Tmax = 0.298	h = −37→29
10587 measured reflections	k = −11→10
3947 independent reflections	l = −18→19

Refinement

Refinement on F^2	49 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.1118P)^2 + 12.0059P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3947 reflections	Δρmax = 1.75 e Å^−3
249 parameters	Δρmin = −1.65 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.15456 (3)	0.60115 (10)	1.08120 (6)	0.0496 (3)
I1	0.18960 (2)	0.66238 (7)	1.25755 (3)	0.0644 (2)
I2	0.16876 (3)	0.36352 (7)	1.02415 (5)	0.0782 (3)
Cl3	0.0476 (7)	0.7569 (19)	0.2918 (14)	0.178 (4)	0.445 (3)
Cl4	0.0674 (4)	1.0477 (14)	0.3291 (9)	0.134 (3)	0.445 (3)
Cl5	0.0678 (18)	0.690 (3)	0.267 (3)	0.178 (4)	0.141 (3)
Cl6	0.0730 (12)	0.947 (3)	0.363 (2)	0.134 (3)	0.141 (3)
Cl7	0.0342 (15)	0.716 (3)	0.277 (3)	0.178 (4)	0.194 (3)
Cl8	0.0682 (9)	0.998 (3)	0.289 (2)	0.134 (3)	0.194 (3)
Cl9	0.0870 (11)	0.846 (2)	0.343 (2)	0.178 (4)	0.220 (3)
Cl10	0.0582 (9)	1.128 (2)	0.3375 (17)	0.134 (3)	0.220 (3)
N1	0.1012 (2)	0.7138 (7)	0.6862 (4)	0.0473 (13)
N2	0.1379 (2)	0.7986 (6)	0.7025 (4)	0.0465 (13)
N3	0.1275 (3)	0.9090 (8)	0.6446 (5)	0.0641 (18)
N4	0.0821 (3)	0.8959 (8)	0.5880 (5)	0.0649 (18)
N5	0.1783 (2)	0.7505 (6)	1.0114 (4)	0.0464 (13)
N6	0.0807 (2)	0.6440 (7)	1.0204 (5)	0.0535 (15)
C1	0.0662 (3)	0.7789 (8)	0.6143 (5)	0.0485 (16)
C2	0.1865 (3)	0.7726 (9)	0.7758 (5)	0.0523 (17)
H2A	0.209836	0.826294	0.761356	0.063*
H2B	0.194248	0.673104	0.775964	0.063*
C3	0.1768 (2)	0.7189 (7)	0.9251 (5)	0.0435 (15)
H3	0.166304	0.629568	0.899813	0.052*
C4	0.1903 (2)	0.8140 (7)	0.8730 (5)	0.0442 (15)
C5	0.2061 (3)	0.9470 (8)	0.9116 (6)	0.0559 (19)
H5	0.215474	1.013677	0.878358	0.067*
C6	0.2076 (3)	0.9782 (9)	0.9992 (6)	0.062 (2)
H6	0.218604	1.066069	1.026760	0.074*
C7	0.1925 (3)	0.8784 (8)	1.0467 (6)	0.0548 (19)
H7	0.192458	0.901926	1.105187	0.066*
C8	0.0488 (3)	0.5764 (9)	0.9431 (6)	0.063 (2)
H8	0.059574	0.500079	0.919179	0.076*
C9	0.0018 (3)	0.6149 (10)	0.8990 (6)	0.066 (2)
H9	−0.019193	0.565566	0.845545	0.079*
C10	−0.0155 (3)	0.7296 (8)	0.9337 (5)	0.0509 (17)
C11	0.0169 (3)	0.7939 (10)	1.0135 (6)	0.068 (2)
H11	0.007030	0.868271	1.040634	0.081*
C12	0.0645 (3)	0.7487 (10)	1.0541 (6)	0.068 (2)
H12	0.086119	0.795064	1.108259	0.082*
C13	0.0803 (17)	0.899 (2)	0.279 (4)	0.152 (7)	0.445 (3)
H13A	0.114769	0.878661	0.310816	0.183*	0.445 (3)
H13B	0.072008	0.915572	0.212366	0.183*	0.445 (3)
C14	0.0894 (17)	0.861 (3)	0.283 (3)	0.040 (10)*	0.141 (3)
H14A	0.124495	0.860038	0.306476	0.048*	0.141 (3)
H14B	0.076207	0.910476	0.222464	0.048*	0.141 (3)
C15	0.0841 (12)	0.822 (3)	0.3003 (11)	0.152 (7)	0.194 (3)
H15A	0.098290	0.798556	0.256194	0.183*	0.194 (3)
H15B	0.108289	0.803794	0.364480	0.183*	0.194 (3)
C16	0.0393 (13)	0.955 (2)	0.329 (7)	0.152 (7)	0.220 (3)
H16A	0.027932	0.935536	0.378026	0.183*	0.220 (3)
H16B	0.012654	0.939009	0.267389	0.183*	0.220 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0468 (5)	0.0584 (5)	0.0417 (4)	0.0039 (4)	0.0165 (4)	0.0029 (4)
I1	0.0624 (4)	0.0826 (4)	0.0410 (3)	0.0021 (3)	0.0144 (2)	0.0003 (2)
I2	0.1000 (5)	0.0644 (4)	0.0826 (5)	0.0093 (3)	0.0504 (4)	0.0088 (3)
Cl3	0.177 (4)	0.175 (4)	0.176 (4)	−0.002 (2)	0.070 (2)	0.004 (2)
Cl4	0.134 (3)	0.135 (3)	0.134 (3)	−0.0008 (19)	0.057 (2)	0.0026 (19)
Cl5	0.177 (4)	0.175 (4)	0.176 (4)	−0.002 (2)	0.070 (2)	0.004 (2)
Cl6	0.134 (3)	0.135 (3)	0.134 (3)	−0.0008 (19)	0.057 (2)	0.0026 (19)
Cl7	0.177 (4)	0.175 (4)	0.176 (4)	−0.002 (2)	0.070 (2)	0.004 (2)
Cl8	0.134 (3)	0.135 (3)	0.134 (3)	−0.0008 (19)	0.057 (2)	0.0026 (19)
Cl9	0.177 (4)	0.175 (4)	0.176 (4)	−0.002 (2)	0.070 (2)	0.004 (2)
Cl10	0.134 (3)	0.135 (3)	0.134 (3)	−0.0008 (19)	0.057 (2)	0.0026 (19)
N1	0.043 (3)	0.056 (3)	0.040 (3)	0.000 (3)	0.014 (2)	0.008 (3)
N2	0.045 (3)	0.052 (3)	0.040 (3)	−0.003 (3)	0.016 (2)	0.005 (3)
N3	0.060 (4)	0.063 (4)	0.058 (4)	−0.007 (3)	0.013 (3)	0.014 (3)
N4	0.056 (4)	0.060 (4)	0.061 (4)	−0.002 (3)	0.006 (3)	0.014 (3)
N5	0.049 (3)	0.045 (3)	0.043 (3)	0.005 (2)	0.017 (3)	−0.003 (2)
N6	0.041 (3)	0.060 (4)	0.052 (3)	0.002 (3)	0.013 (3)	−0.006 (3)
C1	0.049 (4)	0.050 (4)	0.044 (4)	0.004 (3)	0.017 (3)	0.005 (3)
C2	0.043 (4)	0.068 (5)	0.044 (4)	0.000 (3)	0.015 (3)	0.007 (3)
C3	0.040 (4)	0.044 (4)	0.041 (3)	0.002 (3)	0.011 (3)	−0.003 (3)
C4	0.035 (3)	0.046 (4)	0.048 (4)	0.007 (3)	0.013 (3)	0.006 (3)
C5	0.049 (4)	0.044 (4)	0.060 (4)	−0.006 (3)	0.009 (3)	0.008 (3)
C6	0.069 (5)	0.047 (4)	0.054 (4)	0.003 (4)	0.012 (4)	−0.009 (3)
C7	0.058 (5)	0.047 (4)	0.049 (4)	0.011 (3)	0.012 (3)	−0.007 (3)
C8	0.054 (5)	0.066 (5)	0.062 (5)	0.009 (4)	0.017 (4)	−0.020 (4)
C9	0.055 (5)	0.080 (6)	0.053 (4)	0.003 (4)	0.014 (4)	−0.024 (4)
C10	0.053 (4)	0.049 (4)	0.044 (4)	0.002 (3)	0.014 (3)	−0.002 (3)
C11	0.053 (5)	0.069 (5)	0.067 (5)	0.006 (4)	0.011 (4)	−0.030 (4)
C12	0.057 (5)	0.066 (5)	0.060 (5)	0.001 (4)	0.003 (4)	−0.023 (4)
C13	0.152 (7)	0.152 (7)	0.152 (7)	0.0001 (10)	0.064 (3)	0.0000 (10)
C15	0.152 (7)	0.152 (7)	0.152 (7)	0.0001 (10)	0.064 (3)	0.0000 (10)
C16	0.152 (7)	0.152 (7)	0.152 (7)	0.0001 (10)	0.064 (3)	0.0000 (10)

Geometric parameters (Å, º)

Zn1—N6	2.077 (6)	C2—H2B	0.9700
Zn1—N5	2.077 (6)	C3—C4	1.378 (10)
Zn1—I2	2.5160 (13)	C3—H3	0.9300
Zn1—I1	2.5423 (12)	C4—C5	1.388 (10)
Cl3—C13	1.729 (10)	C5—C6	1.366 (12)
Cl4—C13	1.724 (10)	C5—H5	0.9300
Cl5—C14	1.723 (10)	C6—C7	1.384 (12)
Cl6—C14	1.720 (10)	C6—H6	0.9300
Cl7—C15	1.720 (10)	C7—H7	0.9300
Cl7—Cl7^i	1.89 (8)	C8—C9	1.349 (12)
Cl8—C15	1.721 (10)	C8—H8	0.9300
Cl9—C16	1.717 (10)	C9—C10	1.404 (11)
Cl10—C16	1.721 (10)	C9—H9	0.9300
N1—N2	1.308 (8)	C10—C11	1.358 (11)
N1—C1	1.324 (9)	C11—C12	1.380 (12)
N2—N3	1.325 (9)	C11—H11	0.9300
N2—C2	1.456 (9)	C12—H12	0.9300
N3—N4	1.294 (10)	C13—H13A	0.9700
N4—C1	1.335 (10)	C13—H13B	0.9700
N5—C7	1.324 (9)	C14—H14A	0.9700
N5—C3	1.347 (9)	C14—H14B	0.9700
N6—C12	1.305 (11)	C15—H15A	0.9700
N6—C8	1.343 (10)	C15—H15B	0.9700
C1—C10^ii	1.477 (11)	C16—H16A	0.9700
C2—C4	1.508 (10)	C16—H16B	0.9700
C2—H2A	0.9700
N6—Zn1—N5	100.0 (3)	C6—C7—H7	119.0
N6—Zn1—I2	109.02 (18)	N6—C8—C9	122.5 (7)
N5—Zn1—I2	106.24 (16)	N6—C8—H8	118.8
N6—Zn1—I1	109.28 (19)	C9—C8—H8	118.8
N5—Zn1—I1	108.64 (16)	C8—C9—C10	120.0 (7)
I2—Zn1—I1	121.48 (4)	C8—C9—H9	120.0
N2—N1—C1	101.3 (6)	C10—C9—H9	120.0
N1—N2—N3	114.2 (6)	C11—C10—C9	116.6 (7)
N1—N2—C2	123.3 (6)	C11—C10—C1^ii	121.5 (7)
N3—N2—C2	122.5 (6)	C9—C10—C1^ii	121.9 (7)
N4—N3—N2	105.5 (6)	C10—C11—C12	119.9 (8)
N3—N4—C1	106.9 (6)	C10—C11—H11	120.1
C7—N5—C3	118.7 (7)	C12—C11—H11	120.1
C7—N5—Zn1	122.2 (5)	N6—C12—C11	123.3 (7)
C3—N5—Zn1	119.1 (5)	N6—C12—H12	118.3
C12—N6—C8	117.7 (7)	C11—C12—H12	118.3
C12—N6—Zn1	118.8 (5)	Cl4—C13—Cl3	109.7 (14)
C8—N6—Zn1	123.3 (5)	Cl4—C13—H13A	109.7
N1—C1—N4	112.2 (6)	Cl3—C13—H13A	109.7
N1—C1—C10^ii	125.2 (7)	Cl4—C13—H13B	109.7
N4—C1—C10^ii	122.7 (6)	Cl3—C13—H13B	109.7
N2—C2—C4	111.3 (6)	H13A—C13—H13B	108.2
N2—C2—H2A	109.4	Cl6—C14—Cl5	109.7 (13)
C4—C2—H2A	109.4	Cl6—C14—H14A	109.7
N2—C2—H2B	109.4	Cl5—C14—H14A	109.7
C4—C2—H2B	109.4	Cl6—C14—H14B	109.7
H2A—C2—H2B	108.0	Cl5—C14—H14B	109.7
N5—C3—C4	122.5 (7)	H14A—C14—H14B	108.2
N5—C3—H3	118.8	Cl7—C15—Cl8	110.8 (13)
C4—C3—H3	118.8	Cl7—C15—H15A	109.5
C3—C4—C5	118.3 (7)	Cl8—C15—H15A	109.5
C3—C4—C2	119.5 (7)	Cl7—C15—H15B	109.5
C5—C4—C2	122.1 (7)	Cl8—C15—H15B	109.5
C6—C5—C4	118.9 (7)	H15A—C15—H15B	108.1
C6—C5—H5	120.5	Cl9—C16—Cl10	109.1 (13)
C4—C5—H5	120.5	Cl9—C16—H16A	109.9
C5—C6—C7	119.6 (7)	Cl10—C16—H16A	109.9
C5—C6—H6	120.2	Cl9—C16—H16B	109.9
C7—C6—H6	120.2	Cl10—C16—H16B	109.9
N5—C7—C6	121.9 (7)	H16A—C16—H16B	108.3
N5—C7—H7	119.0
C1—N1—N2—N3	−0.7 (8)	C3—C4—C5—C6	−0.1 (11)
C1—N1—N2—C2	−179.0 (7)	C2—C4—C5—C6	178.5 (7)
N1—N2—N3—N4	−0.1 (9)	C4—C5—C6—C7	−1.2 (12)
C2—N2—N3—N4	178.2 (7)	C3—N5—C7—C6	−2.4 (11)
N2—N3—N4—C1	0.9 (9)	Zn1—N5—C7—C6	−179.0 (6)
N2—N1—C1—N4	1.3 (8)	C5—C6—C7—N5	2.5 (12)
N2—N1—C1—C10^ii	−179.6 (7)	C12—N6—C8—C9	1.6 (14)
N3—N4—C1—N1	−1.4 (10)	Zn1—N6—C8—C9	−173.3 (8)
N3—N4—C1—C10^ii	179.4 (7)	N6—C8—C9—C10	−0.1 (15)
N1—N2—C2—C4	−79.4 (9)	C8—C9—C10—C11	−1.8 (14)
N3—N2—C2—C4	102.4 (8)	C8—C9—C10—C1^ii	177.7 (8)
C7—N5—C3—C4	1.0 (10)	C9—C10—C11—C12	2.2 (15)
Zn1—N5—C3—C4	177.7 (5)	C1^ii—C10—C11—C12	−177.3 (9)
N5—C3—C4—C5	0.2 (10)	C8—N6—C12—C11	−1.2 (15)
N5—C3—C4—C2	−178.4 (6)	Zn1—N6—C12—C11	174.0 (8)
N2—C2—C4—C3	85.4 (8)	C10—C11—C12—N6	−0.8 (17)
N2—C2—C4—C5	−93.1 (8)	Cl7^i—Cl7—C15—Cl8	16 (8)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, y, −z+3/2.

catena-Poly[[[diiodidozinc(II)]-µ-4-{2-[(pyridin-3-yl)methyl]-2H-tetrazol-5-yl}pyridine] chloroform monosolvate] (IV)

Crystal data

[ZnI2(C12H10N6)]·CHCl3	Z = 2
Mr = 676.80	F(000) = 636
Triclinic, P1	Dx = 2.190 Mg m^−3
a = 9.804 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.350 (14) Å	Cell parameters from 2745 reflections
c = 11.350 (14) Å	θ = 2.3–20.6°
α = 69.430 (14)°	µ = 4.60 mm^−1
β = 65.912 (18)°	T = 298 K
γ = 65.912 (18)°	Block, yellow
V = 1026 (2) Å^3	0.18 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD area detector diffractometer	3598 independent reflections
Radiation source: fine-focus sealed tube	2424 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.128
phi and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −11→11
Tmin = 0.491, Tmax = 0.631	k = −13→13
5299 measured reflections	l = −13→8

Refinement

Refinement on F^2	48 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.131	H-atom parameters constrained
wR(F^2) = 0.347	w = 1/[σ^2(Fo^2) + (0.172P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max < 0.001
3598 reflections	Δρmax = 2.40 e Å^−3
239 parameters	Δρmin = −1.89 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 > 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.5841 (2)	1.3610 (2)	0.3270 (2)	0.0439 (7)
Cl1	0.3622 (15)	0.1386 (14)	0.269 (2)	0.147 (5)	0.764 (11)
Cl2	0.1101 (13)	0.0460 (13)	0.3467 (18)	0.142 (5)	0.764 (11)
Cl3	0.3996 (17)	−0.0835 (12)	0.1804 (15)	0.142 (5)	0.764 (11)
Cl1'	0.340 (6)	0.093 (5)	0.375 (4)	0.147 (5)	0.236 (11)
Cl2'	0.181 (5)	−0.008 (4)	0.289 (5)	0.142 (5)	0.236 (11)
Cl3'	0.366 (5)	0.158 (3)	0.104 (4)	0.142 (5)	0.236 (11)
I1	0.50273 (18)	1.56525 (14)	0.15560 (15)	0.0610 (6)
I2	0.38647 (17)	1.29240 (15)	0.53999 (15)	0.0613 (6)
N1	0.9929 (17)	0.7202 (15)	0.1936 (16)	0.045 (4)
N2	1.0322 (19)	0.6287 (18)	0.1281 (18)	0.051 (4)
N3	0.973 (3)	0.681 (2)	0.0283 (19)	0.070 (6)
N4	0.896 (3)	0.8072 (18)	0.025 (2)	0.074 (6)
N5	0.7640 (17)	0.3705 (16)	0.3650 (15)	0.043 (4)
N6	0.6984 (18)	1.1970 (16)	0.2453 (17)	0.048 (4)
C1	0.904 (2)	0.8281 (19)	0.1330 (19)	0.044 (4)
C2	1.108 (2)	0.4935 (18)	0.171 (2)	0.050 (5)
H2A	1.195411	0.484101	0.196510	0.060*
H2B	1.149015	0.449294	0.098640	0.060*
C3	0.870 (3)	0.4163 (18)	0.268 (2)	0.050 (5)
H3	0.862289	0.441904	0.182900	0.060*
C4	0.9953 (19)	0.4286 (19)	0.287 (2)	0.043 (4)
C5	1.008 (2)	0.389 (2)	0.410 (3)	0.058 (6)
H5	1.092389	0.394268	0.424452	0.070*
C6	0.902 (3)	0.342 (2)	0.509 (2)	0.061 (6)
H6	0.911978	0.314510	0.593672	0.073*
C7	0.775 (3)	0.3338 (18)	0.492 (2)	0.056 (5)
H7	0.698048	0.303990	0.564855	0.067*
C8	0.708 (3)	1.190 (2)	0.128 (2)	0.063 (6)
H8	0.667647	1.265823	0.070595	0.075*
C9	0.778 (2)	1.0711 (19)	0.089 (2)	0.051 (5)
H9	0.781346	1.070513	0.006349	0.061*
C10	0.842 (2)	0.9558 (16)	0.164 (2)	0.044 (4)
C11	0.837 (3)	0.962 (2)	0.287 (2)	0.059 (6)
H11	0.884030	0.887863	0.342255	0.071*
C12	0.760 (3)	1.082 (2)	0.322 (2)	0.055 (5)
H12	0.749025	1.083913	0.406926	0.066*
C13	0.2770 (18)	0.0662 (17)	0.219 (2)	0.134 (9)	0.764 (11)
H13	0.246658	0.126195	0.140874	0.161*	0.764 (11)
C13'	0.247 (4)	0.120 (4)	0.263 (4)	0.134 (9)	0.236 (11)
H13'	0.154749	0.198219	0.276621	0.161*	0.236 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0411 (13)	0.0429 (13)	0.0629 (15)	−0.0105 (9)	−0.0277 (11)	−0.0178 (10)
Cl1	0.099 (7)	0.109 (8)	0.249 (13)	−0.034 (6)	−0.055 (9)	−0.054 (9)
Cl2	0.092 (8)	0.099 (8)	0.230 (12)	−0.035 (6)	−0.042 (8)	−0.033 (8)
Cl3	0.146 (9)	0.088 (7)	0.182 (11)	0.014 (6)	−0.071 (8)	−0.055 (7)
Cl1'	0.099 (7)	0.109 (8)	0.249 (13)	−0.034 (6)	−0.055 (9)	−0.054 (9)
Cl2'	0.092 (8)	0.099 (8)	0.230 (12)	−0.035 (6)	−0.042 (8)	−0.033 (8)
Cl3'	0.146 (9)	0.088 (7)	0.182 (11)	0.014 (6)	−0.071 (8)	−0.055 (7)
I1	0.0720 (11)	0.0535 (9)	0.0682 (10)	−0.0097 (7)	−0.0450 (8)	−0.0095 (7)
I2	0.0468 (9)	0.0624 (10)	0.0735 (11)	−0.0154 (6)	−0.0160 (7)	−0.0188 (7)
N1	0.034 (9)	0.042 (9)	0.063 (10)	−0.005 (6)	−0.021 (8)	−0.017 (7)
N2	0.041 (10)	0.063 (11)	0.061 (11)	−0.023 (8)	−0.004 (8)	−0.033 (9)
N3	0.104 (17)	0.076 (15)	0.059 (12)	−0.052 (13)	−0.029 (11)	−0.013 (10)
N4	0.118 (18)	0.038 (11)	0.101 (16)	−0.033 (11)	−0.064 (14)	−0.009 (10)
N5	0.029 (8)	0.056 (10)	0.058 (10)	−0.022 (7)	−0.019 (7)	−0.013 (8)
N6	0.046 (10)	0.050 (10)	0.062 (10)	−0.011 (7)	−0.029 (8)	−0.020 (8)
C1	0.047 (12)	0.046 (11)	0.050 (11)	−0.014 (8)	−0.016 (9)	−0.023 (9)
C2	0.028 (10)	0.037 (10)	0.083 (15)	−0.010 (7)	0.003 (9)	−0.037 (10)
C3	0.070 (14)	0.032 (10)	0.071 (13)	−0.012 (9)	−0.041 (11)	−0.018 (9)
C4	0.018 (9)	0.060 (12)	0.057 (12)	−0.001 (7)	−0.011 (8)	−0.033 (9)
C5	0.029 (11)	0.056 (13)	0.094 (18)	0.011 (9)	−0.021 (11)	−0.048 (12)
C6	0.075 (17)	0.061 (14)	0.047 (12)	−0.006 (11)	−0.016 (11)	−0.035 (10)
C7	0.068 (15)	0.033 (11)	0.083 (16)	−0.011 (9)	−0.043 (12)	−0.014 (10)
C8	0.084 (17)	0.064 (14)	0.055 (13)	−0.051 (13)	−0.025 (12)	0.010 (11)
C9	0.062 (13)	0.040 (11)	0.065 (13)	−0.018 (9)	−0.031 (11)	−0.013 (9)
C10	0.035 (10)	0.021 (9)	0.072 (13)	0.011 (7)	−0.027 (9)	−0.019 (8)
C11	0.085 (16)	0.038 (11)	0.065 (14)	0.000 (10)	−0.055 (12)	−0.010 (9)
C12	0.066 (14)	0.051 (13)	0.062 (13)	−0.009 (10)	−0.034 (11)	−0.022 (10)
C13	0.107 (12)	0.083 (12)	0.218 (15)	−0.023 (11)	−0.053 (12)	−0.043 (12)
C13'	0.107 (12)	0.083 (12)	0.218 (15)	−0.023 (11)	−0.053 (12)	−0.043 (12)

Geometric parameters (Å, º)

Zn1—N5^i	2.030 (14)	N4—C1	1.37 (3)
Zn1—N6	2.059 (16)	N5—C3	1.29 (3)
Zn1—I2	2.508 (3)	N5—C7	1.39 (3)
Zn1—I1	2.526 (3)	N6—C8	1.33 (3)
Cl1—C13	1.724 (10)	N6—C12	1.35 (3)
Cl2—C13	1.723 (10)	C1—C10	1.44 (2)
Cl3—C13	1.717 (10)	C2—C4	1.51 (3)
Cl1'—C13'	1.718 (10)	C3—C4	1.40 (3)
Cl2'—C13'	1.716 (10)	C4—C5	1.35 (3)
Cl3'—C13'	1.718 (10)	C5—C6	1.30 (3)
N1—N2	1.33 (2)	C6—C7	1.38 (3)
N1—C1	1.33 (2)	C8—C9	1.37 (3)
N2—N3	1.33 (3)	C9—C10	1.35 (3)
N2—C2	1.41 (3)	C10—C11	1.40 (3)
N3—N4	1.32 (3)	C11—C12	1.37 (3)
N5^i—Zn1—N6	99.7 (6)	N2—C2—C4	111.0 (15)
N5^i—Zn1—I2	109.9 (5)	N5—C3—C4	121.8 (19)
N6—Zn1—I2	105.0 (5)	C5—C4—C3	119.3 (19)
N5^i—Zn1—I1	108.5 (4)	C5—C4—C2	121.5 (19)
N6—Zn1—I1	110.4 (5)	C3—C4—C2	119.1 (19)
I2—Zn1—I1	121.28 (12)	C6—C5—C4	119 (2)
N2—N1—C1	104.6 (17)	C5—C6—C7	122 (2)
N3—N2—N1	110.0 (18)	C6—C7—N5	119 (2)
N3—N2—C2	125.7 (18)	N6—C8—C9	121 (2)
N1—N2—C2	123.7 (19)	C10—C9—C8	124 (2)
N4—N3—N2	109.5 (18)	C9—C10—C11	116.1 (17)
N3—N4—C1	104.3 (19)	C9—C10—C1	126 (2)
C3—N5—C7	118.7 (16)	C11—C10—C1	118.1 (17)
C3—N5—Zn1^ii	118.6 (13)	C12—C11—C10	117.3 (18)
C7—N5—Zn1^ii	122.6 (12)	N6—C12—C11	126 (2)
C8—N6—C12	115.7 (18)	Cl3—C13—Cl2	110.1 (11)
C8—N6—Zn1	127.0 (15)	Cl3—C13—Cl1	112.9 (11)
C12—N6—Zn1	117.2 (14)	Cl2—C13—Cl1	107.0 (10)
N1—C1—N4	111.2 (17)	Cl2'—C13'—Cl3'	112.6 (14)
N1—C1—C10	124.7 (18)	Cl2'—C13'—Cl1'	112.4 (14)
N4—C1—C10	123.5 (19)	Cl3'—C13'—Cl1'	110.7 (14)

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

Hydrogen-bond geometry (Å, º)

Cg1 represents the centroid of the N6-pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1^iii^iii	0.93	2.75	3.64 (2)	160
C13—H13···N4^iv^iv	0.98	2.57	3.45 (3)	150
C13—Cl1···Cg1	1.71 (1)	3.56 (2)	4.799 (16)	127

Symmetry codes: (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z.