Chloridobis(1,10-phenanthroline)zinc(II) tetra-chlorido(1,10-phenan-throline)bis-muthate(III) monohydrate.

In the crystal structure of the title monohydrate salt, [ZnCl(C(12)H(8)N(2))(2)][BiCl(4)(C(12)H(8)N(2))]·H(2)O, the ionic components are linked into three-dimensional supra-molecular channels by five pairs of C-H⋯Cl hydrogen bonds and π-π stacking inter-actions with an inter-planar distance of 3.643 (2) Å. The solvent water mol-ecules are lodged in the channels.

Related literature

For related bis­muth compounds, see: James et al. (2000 ▶); Jarraya et al. (1995 ▶); Bowmaker et al. (1998 ▶). For a related [Zn(phen)2Cl]+ coordinated cation structure, see: Yu & Zhang (2006 ▶). For supra­molecular systems containing halometallate groups as their main component, see: Mitzi & Brock (2001 ▶); Zhu et al. (2003 ▶); Papavassiliou et al. (1995 ▶); Pohl et al. (1994 ▶); Carmalt et al. (1995 ▶). For π–π inter­actions, see: Chandrasekhar et al. (2006 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

.

Experimental

Crystal data

[ZnCl(C12H8N2)2][BiCl4(C12H8N2)]·H2O

M = 1010.25

Triclinic,

a = 9.748 (2) Å

b = 13.694 (4) Å

c = 14.249 (4) Å

α = 86.848 (7)°

β = 74.660 (5)°

γ = 80.692 (7)°

V = 1810.0 (8) Å3

Z = 2

Mo Kα radiation

μ = 5.93 mm−1

T = 293 K

0.40 × 0.30 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.200, T max = 0.269

13923 measured reflections

8140 independent reflections

7571 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.061

S = 1.03

8140 reflections

451 parameters

H-atom parameters constrained

Δρmax = 1.76 e Å−3

Δρmin = −1.03 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052682/bg2383sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052682/bg2383Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnCl(C12H8N2)2][BiCl4(C12H8N2)]·H2O	Z = 2
Mr = 1010.25	F(000) = 980
Triclinic, P1	Dx = 1.854 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.748 (2) Å	Cell parameters from 5205 reflections
b = 13.694 (4) Å	θ = 2.1–27.5°
c = 14.249 (4) Å	µ = 5.93 mm−1
α = 86.848 (7)°	T = 293 K
β = 74.660 (5)°	Block, yellow
γ = 80.692 (7)°	0.40 × 0.30 × 0.30 mm
V = 1810.0 (8) Å3

Rigaku R-AXIS RAPID diffractometer	8140 independent reflections
Radiation source: fine-focus sealed tube	7571 reflections with I > 2σ(I)
graphite	Rint = 0.012
Detector resolution: 14.6306 pixels mm-1	θmax = 27.5°, θmin = 2.1°
CCD_Profile_fitting scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
Tmin = 0.200, Tmax = 0.269	l = −18→15
13923 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.035P)2 + 0.8909P] where P = (Fo2 + 2Fc2)/3
8140 reflections	(Δ/σ)max = 0.003
451 parameters	Δρmax = 1.76 e Å−3
0 restraints	Δρmin = −1.03 e Å−3

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.

	x	y	z	Uiso*/Ueq
Bi1	0.187173 (6)	0.746413 (5)	0.167412 (4)	0.03413 (2)
Zn1	0.78062 (2)	0.150812 (15)	0.327965 (15)	0.03602 (5)
Cl1	0.40709 (6)	0.82384 (5)	0.04129 (4)	0.06274 (16)
Cl3	0.35492 (8)	0.63095 (6)	0.27504 (5)	0.0836 (2)
Cl4	0.01178 (7)	0.82443 (4)	0.06630 (5)	0.07034 (15)
Cl5	0.62441 (5)	0.27909 (4)	0.29060 (5)	0.05442 (14)
Cl2	0.03588 (6)	0.85536 (4)	0.32106 (4)	0.06049 (15)
O1	0.4158 (4)	0.4571 (2)	0.4424 (2)	0.1368 (12)
N1	0.24551 (18)	0.60304 (12)	0.05446 (12)	0.0432 (4)
N2	0.01895 (17)	0.62449 (12)	0.21779 (12)	0.0430 (4)
N3	0.98388 (15)	0.12811 (11)	0.23401 (11)	0.0347 (4)
N4	0.89400 (17)	0.24614 (12)	0.39095 (12)	0.0404 (4)
N5	0.75232 (16)	0.04934 (12)	0.44323 (11)	0.0385 (4)
N6	0.68957 (17)	0.04085 (12)	0.27109 (11)	0.0412 (4)
C1	0.3532 (3)	0.59510 (18)	−0.02525 (16)	0.0569 (6)
H1	0.4077	0.6462	−0.0419	0.068*
C2	0.3879 (3)	0.5125 (2)	−0.08527 (18)	0.0699 (8)
H2	0.4652	0.5084	−0.1403	0.084*
C3	0.3071 (3)	0.43848 (18)	−0.06212 (17)	0.0719 (7)
H3	0.3304	0.3826	−0.1008	0.086*
C4	0.1870 (3)	0.44578 (15)	0.02089 (16)	0.0568 (6)
C5	0.1617 (2)	0.53089 (14)	0.07824 (14)	0.0428 (5)
C6	0.0902 (3)	0.37504 (16)	0.04618 (19)	0.0721 (6)
H6	0.1071	0.3189	0.0084	0.087*
C7	−0.0242 (3)	0.38787 (16)	0.12303 (19)	0.0695 (6)
H7	−0.0870	0.3415	0.1366	0.083*
C8	−0.0520 (2)	0.47192 (15)	0.18510 (17)	0.0549 (5)
C9	0.0414 (2)	0.54307 (14)	0.16269 (14)	0.0420 (5)
C10	−0.1687 (3)	0.48762 (18)	0.2676 (2)	0.0683 (7)
H10	−0.2324	0.4419	0.2848	0.082*
C11	−0.1894 (3)	0.5695 (2)	0.3228 (2)	0.0694 (8)
H11	−0.2667	0.5801	0.3776	0.083*
C12	−0.0926 (2)	0.63737 (18)	0.29562 (18)	0.0554 (6)
H12	−0.1068	0.6933	0.3332	0.067*
C13	1.0301 (2)	0.06529 (15)	0.16107 (14)	0.0437 (5)
H13	0.9688	0.0232	0.1521	0.052*
C14	1.1661 (2)	0.05940 (17)	0.09739 (15)	0.0526 (6)
H14	1.1949	0.0137	0.0473	0.063*
C15	1.2568 (2)	0.12066 (18)	0.10860 (16)	0.0530 (6)
H15	1.3479	0.1176	0.0659	0.064*
C16	1.2123 (2)	0.18894 (15)	0.18524 (14)	0.0416 (5)
C17	1.07434 (18)	0.18846 (13)	0.24784 (12)	0.0331 (4)
C18	1.2984 (2)	0.25820 (17)	0.20192 (17)	0.0519 (6)
H18	1.3886	0.2605	0.1594	0.062*
C19	1.2519 (2)	0.31960 (16)	0.27741 (18)	0.0536 (6)
H19	1.3092	0.3650	0.2854	0.064*
C20	1.1157 (2)	0.31706 (14)	0.34626 (16)	0.0456 (5)
C21	1.02573 (18)	0.25202 (13)	0.33039 (13)	0.0358 (4)
C22	1.0659 (3)	0.37315 (16)	0.43134 (18)	0.0578 (6)
H22	1.1224	0.4159	0.4458	0.069*
C23	0.9347 (3)	0.36507 (16)	0.49287 (17)	0.0591 (6)
H23	0.9023	0.4011	0.5501	0.071*
C24	0.8495 (2)	0.30251 (16)	0.46956 (16)	0.0503 (6)
H24	0.7583	0.3001	0.5104	0.060*
C25	0.7844 (2)	0.05377 (17)	0.52733 (15)	0.0505 (6)
H25	0.8275	0.1065	0.5380	0.061*
C26	0.7559 (3)	−0.01784 (19)	0.60065 (17)	0.0638 (7)
H26	0.7792	−0.0120	0.6591	0.077*
C27	0.6945 (3)	−0.09541 (18)	0.58647 (17)	0.0606 (7)
H27	0.6725	−0.1421	0.6359	0.073*
C28	0.6640 (2)	−0.10539 (15)	0.49649 (16)	0.0472 (6)
C29	0.69474 (18)	−0.03026 (13)	0.42664 (14)	0.0369 (4)
C30	0.6035 (2)	−0.18692 (17)	0.47345 (19)	0.0613 (7)
H30	0.5856	−0.2380	0.5187	0.074*
C31	0.5726 (2)	−0.19043 (17)	0.3879 (2)	0.0610 (7)
H31	0.5316	−0.2435	0.3754	0.073*
C32	0.6008 (2)	−0.11468 (15)	0.31452 (17)	0.0482 (6)
C33	0.66186 (18)	−0.03468 (14)	0.33480 (14)	0.0378 (5)
C34	0.5661 (2)	−0.11203 (18)	0.22484 (18)	0.0595 (6)
H34	0.5259	−0.1635	0.2081	0.071*
C35	0.5913 (2)	−0.03448 (19)	0.16243 (17)	0.0596 (6)
H35	0.5667	−0.0320	0.1035	0.071*
C36	0.6542 (2)	0.04149 (17)	0.18741 (16)	0.0518 (6)
H36	0.6719	0.0941	0.1441	0.062*

	U11	U22	U33	U12	U13	U23
Bi1	0.03586 (3)	0.03625 (3)	0.03228 (3)	−0.00975 (2)	−0.00893 (2)	−0.00470 (2)
Zn1	0.03522 (9)	0.03824 (10)	0.03538 (10)	−0.00949 (8)	−0.00859 (8)	0.00157 (8)
Cl1	0.0602 (3)	0.0771 (3)	0.0524 (3)	−0.0367 (2)	−0.0012 (2)	−0.0027 (2)
Cl3	0.0772 (4)	0.1053 (5)	0.0550 (3)	0.0289 (4)	−0.0178 (3)	−0.0103 (3)
Cl4	0.0946 (3)	0.0496 (3)	0.0893 (3)	−0.0090 (3)	−0.0637 (3)	−0.0025 (2)
Cl5	0.0441 (2)	0.0436 (2)	0.0793 (3)	−0.00778 (19)	−0.0237 (2)	0.0085 (2)
Cl2	0.0624 (3)	0.0617 (3)	0.0540 (3)	0.0005 (2)	−0.0108 (2)	−0.0227 (2)
O1	0.147 (2)	0.143 (2)	0.117 (2)	−0.033 (2)	−0.0196 (19)	−0.0161 (19)
N1	0.0500 (8)	0.0410 (8)	0.0382 (8)	−0.0010 (7)	−0.0127 (7)	−0.0069 (6)
N2	0.0451 (8)	0.0410 (8)	0.0453 (8)	−0.0138 (6)	−0.0118 (7)	0.0009 (7)
N3	0.0368 (7)	0.0334 (7)	0.0332 (7)	−0.0038 (6)	−0.0088 (6)	0.0005 (6)
N4	0.0410 (7)	0.0396 (7)	0.0414 (8)	−0.0051 (6)	−0.0114 (6)	−0.0062 (6)
N5	0.0396 (7)	0.0403 (8)	0.0351 (7)	−0.0013 (6)	−0.0119 (6)	0.0014 (6)
N6	0.0454 (7)	0.0444 (8)	0.0390 (8)	−0.0134 (6)	−0.0164 (6)	0.0018 (6)
C1	0.0560 (12)	0.0624 (13)	0.0489 (11)	0.0006 (10)	−0.0109 (10)	−0.0132 (10)
C2	0.0759 (15)	0.0763 (15)	0.0503 (12)	0.0219 (13)	−0.0187 (11)	−0.0278 (11)
C3	0.1028 (16)	0.0555 (12)	0.0625 (12)	0.0276 (12)	−0.0483 (11)	−0.0279 (10)
C4	0.0866 (12)	0.0337 (9)	0.0613 (10)	0.0111 (9)	−0.0489 (9)	−0.0104 (8)
C5	0.0569 (9)	0.0329 (8)	0.0471 (9)	−0.0016 (7)	−0.0315 (7)	−0.0014 (7)
C6	0.1195 (14)	0.0295 (9)	0.0942 (13)	0.0001 (10)	−0.0803 (11)	−0.0059 (9)
C7	0.1020 (13)	0.0343 (9)	0.1019 (14)	−0.0225 (9)	−0.0745 (11)	0.0173 (10)
C8	0.0716 (10)	0.0383 (9)	0.0753 (11)	−0.0222 (8)	−0.0511 (9)	0.0218 (8)
C9	0.0506 (9)	0.0354 (8)	0.0496 (9)	−0.0100 (7)	−0.0295 (7)	0.0094 (7)
C10	0.0674 (11)	0.0634 (12)	0.0915 (15)	−0.0389 (10)	−0.0414 (11)	0.0387 (11)
C11	0.0554 (12)	0.0791 (15)	0.0740 (16)	−0.0308 (11)	−0.0097 (12)	0.0206 (13)
C12	0.0490 (10)	0.0583 (12)	0.0583 (13)	−0.0170 (9)	−0.0080 (10)	0.0022 (10)
C13	0.0487 (9)	0.0429 (9)	0.0400 (9)	−0.0067 (8)	−0.0118 (8)	−0.0043 (8)
C14	0.0557 (11)	0.0562 (12)	0.0382 (10)	−0.0004 (10)	−0.0025 (9)	−0.0071 (9)
C15	0.0394 (10)	0.0659 (13)	0.0440 (11)	−0.0014 (10)	0.0011 (9)	0.0035 (10)
C16	0.0341 (8)	0.0483 (10)	0.0405 (9)	−0.0041 (8)	−0.0101 (7)	0.0107 (8)
C17	0.0340 (7)	0.0338 (8)	0.0329 (8)	−0.0036 (6)	−0.0134 (6)	0.0057 (6)
C18	0.0347 (8)	0.0642 (12)	0.0584 (12)	−0.0164 (8)	−0.0129 (8)	0.0159 (10)
C19	0.0462 (9)	0.0524 (11)	0.0710 (13)	−0.0209 (8)	−0.0251 (9)	0.0109 (10)
C20	0.0505 (9)	0.0366 (9)	0.0594 (11)	−0.0109 (8)	−0.0297 (8)	0.0038 (8)
C21	0.0367 (8)	0.0327 (8)	0.0414 (9)	−0.0045 (7)	−0.0171 (7)	0.0013 (7)
C22	0.0693 (11)	0.0424 (10)	0.0745 (13)	−0.0137 (9)	−0.0362 (10)	−0.0084 (9)
C23	0.0770 (14)	0.0485 (11)	0.0558 (12)	−0.0079 (10)	−0.0216 (10)	−0.0190 (9)
C24	0.0558 (11)	0.0478 (10)	0.0458 (10)	−0.0064 (9)	−0.0092 (9)	−0.0114 (8)
C25	0.0591 (11)	0.0534 (11)	0.0411 (10)	−0.0002 (9)	−0.0219 (8)	0.0015 (9)
C26	0.0781 (14)	0.0688 (15)	0.0427 (11)	0.0056 (12)	−0.0243 (10)	0.0070 (10)
C27	0.0637 (13)	0.0607 (13)	0.0459 (11)	0.0065 (11)	−0.0078 (10)	0.0189 (10)
C28	0.0383 (9)	0.0436 (10)	0.0500 (11)	0.0023 (8)	−0.0014 (8)	0.0089 (9)
C29	0.0285 (7)	0.0381 (9)	0.0391 (9)	−0.0002 (7)	−0.0036 (7)	0.0029 (7)
C30	0.0521 (11)	0.0488 (11)	0.0740 (15)	−0.0122 (10)	−0.0022 (11)	0.0196 (11)
C31	0.0511 (11)	0.0444 (10)	0.0840 (17)	−0.0184 (9)	−0.0058 (11)	0.0039 (11)
C32	0.0394 (9)	0.0416 (9)	0.0618 (12)	−0.0105 (8)	−0.0064 (9)	−0.0055 (9)
C33	0.0293 (7)	0.0401 (9)	0.0419 (9)	−0.0055 (7)	−0.0053 (7)	−0.0004 (7)
C34	0.0540 (10)	0.0629 (12)	0.0679 (13)	−0.0198 (10)	−0.0170 (10)	−0.0164 (10)
C35	0.0634 (11)	0.0718 (13)	0.0526 (11)	−0.0185 (11)	−0.0236 (9)	−0.0124 (10)
C36	0.0611 (11)	0.0574 (11)	0.0429 (10)	−0.0173 (9)	−0.0194 (9)	0.0016 (9)

Bi1—N2	2.4745 (17)	C12—H12	0.9300
Bi1—N1	2.5041 (17)	C13—C14	1.387 (3)
Bi1—Cl4	2.5853 (8)	C13—H13	0.9300
Bi1—Cl2	2.6708 (8)	C14—C15	1.356 (4)
Bi1—Cl1	2.7271 (7)	C14—H14	0.9300
Bi1—Cl3	2.7838 (9)	C15—C16	1.409 (3)
Zn1—N3	2.0635 (14)	C15—H15	0.9300
Zn1—N5	2.0828 (16)	C16—C17	1.404 (2)
Zn1—N6	2.1586 (18)	C16—C18	1.431 (3)
Zn1—N4	2.2026 (18)	C17—C21	1.432 (2)
Zn1—Cl5	2.2690 (7)	C18—C19	1.337 (3)
N1—C1	1.323 (3)	C18—H18	0.9300
N1—C5	1.355 (3)	C19—C20	1.431 (3)
N2—C12	1.329 (3)	C19—H19	0.9300
N2—C9	1.354 (3)	C20—C22	1.402 (3)
N3—C13	1.322 (2)	C20—C21	1.412 (3)
N3—C17	1.358 (2)	C22—C23	1.363 (3)
N4—C24	1.330 (3)	C22—H22	0.9300
N4—C21	1.356 (2)	C23—C24	1.393 (3)
N5—C25	1.323 (3)	C23—H23	0.9300
N5—C29	1.362 (3)	C24—H24	0.9300
N6—C36	1.325 (3)	C25—C26	1.397 (3)
N6—C33	1.351 (2)	C25—H25	0.9300
C1—C2	1.398 (3)	C26—C27	1.349 (4)
C1—H1	0.9300	C26—H26	0.9300
C2—C3	1.357 (4)	C27—C28	1.409 (4)
C2—H2	0.9300	C27—H27	0.9300
C3—C4	1.422 (3)	C28—C29	1.403 (3)
C3—H3	0.9300	C28—C30	1.434 (3)
C4—C5	1.411 (3)	C29—C33	1.434 (3)
C4—C6	1.427 (3)	C30—C31	1.336 (4)
C5—C9	1.436 (3)	C30—H30	0.9300
C6—C7	1.336 (4)	C31—C32	1.437 (3)
C6—H6	0.9300	C31—H31	0.9300
C7—C8	1.437 (3)	C32—C34	1.403 (4)
C7—H7	0.9300	C32—C33	1.405 (3)
C8—C10	1.401 (3)	C34—C35	1.358 (4)
C8—C9	1.407 (3)	C34—H34	0.9300
C10—C11	1.363 (4)	C35—C36	1.396 (3)
C10—H10	0.9300	C35—H35	0.9300
C11—C12	1.397 (3)	C36—H36	0.9300
C11—H11	0.9300
N2—Bi1—N1	66.87 (6)	N2—C12—C11	122.1 (2)
N2—Bi1—Cl4	84.27 (5)	N2—C12—H12	119.0
N1—Bi1—Cl4	85.90 (5)	C11—C12—H12	119.0
N2—Bi1—Cl2	88.88 (4)	N3—C13—C14	122.8 (2)
N1—Bi1—Cl2	155.73 (4)	N3—C13—H13	118.6
Cl4—Bi1—Cl2	91.03 (3)	C14—C13—H13	118.6
N2—Bi1—Cl1	153.56 (4)	C15—C14—C13	119.6 (2)
N1—Bi1—Cl1	86.95 (4)	C15—C14—H14	120.2
Cl4—Bi1—Cl1	90.49 (3)	C13—C14—H14	120.2
Cl2—Bi1—Cl1	117.18 (2)	C14—C15—C16	119.66 (18)
N2—Bi1—Cl3	86.01 (5)	C14—C15—H15	120.2
N1—Bi1—Cl3	86.63 (5)	C16—C15—H15	120.2
Cl4—Bi1—Cl3	169.50 (2)	C17—C16—C15	117.14 (19)
Cl2—Bi1—Cl3	92.75 (3)	C17—C16—C18	118.88 (18)
Cl1—Bi1—Cl3	96.48 (3)	C15—C16—C18	123.98 (18)
N3—Zn1—N5	113.48 (6)	N3—C17—C16	122.25 (16)
N3—Zn1—N6	98.12 (6)	N3—C17—C21	117.79 (15)
N5—Zn1—N6	78.81 (7)	C16—C17—C21	119.95 (17)
N3—Zn1—N4	78.42 (6)	C19—C18—C16	121.28 (18)
N5—Zn1—N4	96.10 (7)	C19—C18—H18	119.4
N6—Zn1—N4	172.24 (6)	C16—C18—H18	119.4
N3—Zn1—Cl5	116.25 (5)	C18—C19—C20	121.5 (2)
N5—Zn1—Cl5	130.27 (4)	C18—C19—H19	119.3
N6—Zn1—Cl5	93.82 (5)	C20—C19—H19	119.3
N4—Zn1—Cl5	93.95 (5)	C22—C20—C21	116.82 (18)
C1—N1—C5	119.74 (18)	C22—C20—C19	124.3 (2)
C1—N1—Bi1	123.11 (15)	C21—C20—C19	118.81 (19)
C5—N1—Bi1	117.14 (12)	N4—C21—C20	122.70 (17)
C12—N2—C9	119.59 (18)	N4—C21—C17	117.84 (17)
C12—N2—Bi1	122.15 (15)	C20—C21—C17	119.46 (16)
C9—N2—Bi1	118.25 (12)	C23—C22—C20	120.0 (2)
C13—N3—C17	118.48 (15)	C23—C22—H22	120.0
C13—N3—Zn1	126.69 (14)	C20—C22—H22	120.0
C17—N3—Zn1	114.75 (11)	C22—C23—C24	119.6 (2)
C24—N4—C21	118.43 (18)	C22—C23—H23	120.2
C24—N4—Zn1	131.04 (14)	C24—C23—H23	120.2
C21—N4—Zn1	110.17 (12)	N4—C24—C23	122.4 (2)
C25—N5—C29	118.35 (17)	N4—C24—H24	118.8
C25—N5—Zn1	127.75 (15)	C23—C24—H24	118.8
C29—N5—Zn1	113.89 (13)	N5—C25—C26	122.4 (2)
C36—N6—C33	119.11 (18)	N5—C25—H25	118.8
C36—N6—Zn1	128.84 (14)	C26—C25—H25	118.8
C33—N6—Zn1	111.98 (13)	C27—C26—C25	119.9 (2)
N1—C1—C2	122.3 (2)	C27—C26—H26	120.1
N1—C1—H1	118.9	C25—C26—H26	120.1
C2—C1—H1	118.9	C26—C27—C28	119.7 (2)
C3—C2—C1	119.1 (2)	C26—C27—H27	120.2
C3—C2—H2	120.5	C28—C27—H27	120.2
C1—C2—H2	120.5	C29—C28—C27	117.1 (2)
C2—C3—C4	120.4 (2)	C29—C28—C30	119.1 (2)
C2—C3—H3	119.8	C27—C28—C30	123.7 (2)
C4—C3—H3	119.8	N5—C29—C28	122.45 (19)
C5—C4—C3	116.5 (2)	N5—C29—C33	117.80 (16)
C5—C4—C6	119.4 (2)	C28—C29—C33	119.74 (19)
C3—C4—C6	124.0 (2)	C31—C30—C28	120.8 (2)
N1—C5—C4	121.85 (18)	C31—C30—H30	119.6
N1—C5—C9	118.84 (17)	C28—C30—H30	119.6
C4—C5—C9	119.29 (19)	C30—C31—C32	122.0 (2)
C7—C6—C4	121.3 (2)	C30—C31—H31	119.0
C7—C6—H6	119.4	C32—C31—H31	119.0
C4—C6—H6	119.4	C34—C32—C33	116.9 (2)
C6—C7—C8	121.3 (2)	C34—C32—C31	124.8 (2)
C6—C7—H7	119.4	C33—C32—C31	118.3 (2)
C8—C7—H7	119.4	N6—C33—C32	122.45 (19)
C10—C8—C9	117.5 (2)	N6—C33—C29	117.52 (17)
C10—C8—C7	123.4 (2)	C32—C33—C29	120.03 (18)
C9—C8—C7	119.1 (2)	C35—C34—C32	120.1 (2)
N2—C9—C8	121.52 (18)	C35—C34—H34	119.9
N2—C9—C5	118.83 (17)	C32—C34—H34	119.9
C8—C9—C5	119.63 (18)	C34—C35—C36	119.5 (2)
C11—C10—C8	120.3 (2)	C34—C35—H35	120.2
C11—C10—H10	119.8	C36—C35—H35	120.2
C8—C10—H10	119.8	N6—C36—C35	121.9 (2)
C10—C11—C12	119.0 (2)	N6—C36—H36	119.0
C10—C11—H11	120.5	C35—C36—H36	119.0
C12—C11—H11	120.5
N2—Bi1—N1—C1	178.34 (19)	C7—C8—C10—C11	−179.4 (2)
Cl4—Bi1—N1—C1	92.83 (17)	C8—C10—C11—C12	0.1 (4)
Cl2—Bi1—N1—C1	176.22 (14)	C9—N2—C12—C11	−0.4 (4)
Cl1—Bi1—N1—C1	2.12 (17)	Bi1—N2—C12—C11	178.55 (19)
Cl3—Bi1—N1—C1	−94.56 (17)	C10—C11—C12—N2	−0.1 (4)
N2—Bi1—N1—C5	−2.14 (14)	C17—N3—C13—C14	−0.9 (3)
Cl4—Bi1—N1—C5	−87.65 (14)	Zn1—N3—C13—C14	175.64 (16)
Cl2—Bi1—N1—C5	−4.3 (2)	N3—C13—C14—C15	−0.6 (3)
Cl1—Bi1—N1—C5	−178.36 (14)	C13—C14—C15—C16	0.5 (3)
Cl3—Bi1—N1—C5	84.96 (14)	C14—C15—C16—C17	1.0 (3)
N1—Bi1—N2—C12	−178.07 (19)	C14—C15—C16—C18	−178.5 (2)
Cl4—Bi1—N2—C12	−90.09 (17)	C13—N3—C17—C16	2.6 (3)
Cl2—Bi1—N2—C12	1.06 (17)	Zn1—N3—C17—C16	−174.40 (14)
Cl1—Bi1—N2—C12	−169.56 (14)	C13—N3—C17—C21	−176.49 (17)
Cl3—Bi1—N2—C12	93.90 (17)	Zn1—N3—C17—C21	6.5 (2)
N1—Bi1—N2—C9	0.89 (14)	C15—C16—C17—N3	−2.6 (3)
Cl4—Bi1—N2—C9	88.87 (14)	C18—C16—C17—N3	176.91 (18)
Cl2—Bi1—N2—C9	−179.98 (14)	C15—C16—C17—C21	176.45 (18)
Cl1—Bi1—N2—C9	9.4 (2)	C18—C16—C17—C21	−4.1 (3)
Cl3—Bi1—N2—C9	−87.14 (14)	C17—C16—C18—C19	2.2 (3)
N5—Zn1—N3—C13	83.48 (17)	C15—C16—C18—C19	−178.3 (2)
N6—Zn1—N3—C13	2.21 (17)	C16—C18—C19—C20	1.7 (3)
N4—Zn1—N3—C13	175.16 (17)	C18—C19—C20—C22	174.2 (2)
Cl5—Zn1—N3—C13	−96.15 (16)	C18—C19—C20—C21	−3.7 (3)
N5—Zn1—N3—C17	−99.84 (13)	C24—N4—C21—C20	−1.5 (3)
N6—Zn1—N3—C17	178.89 (12)	Zn1—N4—C21—C20	172.35 (15)
N4—Zn1—N3—C17	−8.17 (12)	C24—N4—C21—C17	177.89 (18)
Cl5—Zn1—N3—C17	80.53 (13)	Zn1—N4—C21—C17	−8.2 (2)
N3—Zn1—N4—C24	−178.41 (19)	C22—C20—C21—N4	3.1 (3)
N5—Zn1—N4—C24	−65.64 (19)	C19—C20—C21—N4	−178.80 (19)
Cl5—Zn1—N4—C24	65.59 (18)	C22—C20—C21—C17	−176.29 (18)
N3—Zn1—N4—C21	8.74 (12)	C19—C20—C21—C17	1.8 (3)
N5—Zn1—N4—C21	121.51 (12)	N3—C17—C21—N4	1.7 (2)
Cl5—Zn1—N4—C21	−107.27 (12)	C16—C17—C21—N4	−177.41 (17)
N3—Zn1—N5—C25	85.42 (17)	N3—C17—C21—C20	−178.89 (17)
N6—Zn1—N5—C25	179.49 (17)	C16—C17—C21—C20	2.0 (3)
N4—Zn1—N5—C25	5.42 (16)	C21—C20—C22—C23	−1.6 (3)
Cl5—Zn1—N5—C25	−95.02 (16)	C19—C20—C22—C23	−179.5 (2)
N3—Zn1—N5—C29	−94.02 (12)	C20—C22—C23—C24	−1.4 (4)
N6—Zn1—N5—C29	0.06 (11)	C21—N4—C24—C23	−1.7 (3)
N4—Zn1—N5—C29	−174.01 (11)	Zn1—N4—C24—C23	−174.04 (17)
Cl5—Zn1—N5—C29	85.55 (12)	C22—C23—C24—N4	3.2 (4)
N3—Zn1—N6—C36	−70.90 (17)	C29—N5—C25—C26	−2.7 (3)
N5—Zn1—N6—C36	176.64 (17)	Zn1—N5—C25—C26	177.91 (16)
Cl5—Zn1—N6—C36	46.31 (17)	N5—C25—C26—C27	0.5 (3)
N3—Zn1—N6—C33	112.22 (12)	C25—C26—C27—C28	2.1 (3)
N5—Zn1—N6—C33	−0.24 (11)	C26—C27—C28—C29	−2.5 (3)
Cl5—Zn1—N6—C33	−130.57 (11)	C26—C27—C28—C30	177.8 (2)
C5—N1—C1—C2	−2.3 (3)	C25—N5—C29—C28	2.2 (3)
Bi1—N1—C1—C2	177.25 (19)	Zn1—N5—C29—C28	−178.29 (13)
N1—C1—C2—C3	1.1 (4)	C25—N5—C29—C33	−179.36 (16)
C1—C2—C3—C4	1.3 (4)	Zn1—N5—C29—C33	0.13 (19)
C2—C3—C4—C5	−2.5 (4)	C27—C28—C29—N5	0.3 (3)
C2—C3—C4—C6	175.1 (2)	C30—C28—C29—N5	−179.94 (17)
C1—N1—C5—C4	0.9 (3)	C27—C28—C29—C33	−178.05 (17)
Bi1—N1—C5—C4	−178.59 (15)	C30—C28—C29—C33	1.7 (3)
C1—N1—C5—C9	−177.2 (2)	C29—C28—C30—C31	−2.0 (3)
Bi1—N1—C5—C9	3.2 (2)	C27—C28—C30—C31	177.8 (2)
C3—C4—C5—N1	1.4 (3)	C28—C30—C31—C32	1.3 (3)
C6—C4—C5—N1	−176.3 (2)	C30—C31—C32—C34	−177.5 (2)
C3—C4—C5—C9	179.5 (2)	C30—C31—C32—C33	−0.4 (3)
C6—C4—C5—C9	1.9 (3)	C36—N6—C33—C32	2.1 (3)
C5—C4—C6—C7	0.1 (4)	Zn1—N6—C33—C32	179.28 (13)
C3—C4—C6—C7	−177.3 (2)	C36—N6—C33—C29	−176.84 (16)
C4—C6—C7—C8	−1.9 (4)	Zn1—N6—C33—C29	0.38 (19)
C6—C7—C8—C10	−178.7 (2)	C34—C32—C33—N6	−1.4 (3)
C6—C7—C8—C9	1.6 (4)	C31—C32—C33—N6	−178.71 (17)
C12—N2—C9—C8	0.8 (3)	C34—C32—C33—C29	177.48 (17)
Bi1—N2—C9—C8	−178.14 (15)	C31—C32—C33—C29	0.2 (3)
C12—N2—C9—C5	179.3 (2)	N5—C29—C33—N6	−0.4 (2)
Bi1—N2—C9—C5	0.4 (2)	C28—C29—C33—N6	178.11 (16)
C10—C8—C9—N2	−0.8 (3)	N5—C29—C33—C32	−179.28 (15)
C7—C8—C9—N2	178.9 (2)	C28—C29—C33—C32	−0.8 (2)
C10—C8—C9—C5	−179.3 (2)	C33—C32—C34—C35	−0.3 (3)
C7—C8—C9—C5	0.4 (3)	C31—C32—C34—C35	176.9 (2)
N1—C5—C9—N2	−2.4 (3)	C32—C34—C35—C36	1.2 (3)
C4—C5—C9—N2	179.33 (19)	C33—N6—C36—C35	−1.1 (3)
N1—C5—C9—C8	176.08 (19)	Zn1—N6—C36—C35	−177.77 (15)
C4—C5—C9—C8	−2.1 (3)	C34—C35—C36—N6	−0.5 (3)
C9—C8—C10—C11	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl3i	0.93	2.82	3.588 (4)	141.
C6—H6···Cl4ii	0.93	2.82	3.637 (4)	147.
C10—H10···Cl5iii	0.93	2.80	3.707 (4)	164.
C15—H15···Cl1iv	0.93	2.69	3.579 (4)	160.
C25—H25···Cl2v	0.93	2.80	3.506 (4)	134.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl3i	0.93	2.82	3.588 (4)	141
C6—H6⋯Cl4ii	0.93	2.82	3.637 (4)	147
C10—H10⋯Cl5iii	0.93	2.80	3.707 (4)	164
C15—H15⋯Cl1iv	0.93	2.69	3.579 (4)	160
C25—H25⋯Cl2v	0.93	2.80	3.506 (4)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .