Bis{1,2-bis-[2-(1H-imidazol-1-yl)eth-oxy]ethane-κN,N}dichloridocadmium(II) monohydrate.

The asymmetric unit of the title compound, [CdCl(2)(C(12)H(18)N(4)O(2))(2)]·H(2)O, contains one water mol-ecule and two halves of a [CdCl(2)(BIEE)(2)] complex mol-ecule {BIEE is 1,2-bis-[2-(1H-imidazol-1-yl)eth-oxy]ethane}, with the Cd(II) atoms lying on inversion centres. Each metal atom displays an elongated octa-hedral coordination geometry provided by two trans-arranged chloride anions and four N atoms from two BIEE ligands. Weak O-H⋯Cl hydrogen-bond inter-actions contribute to the stability of the crystal packing.

Related literature

For general background to flexible bis­(imidazole) ligands, see: Liu et al. (2007 ▶); Wen et al. (2007 ▶); Jin et al. (2006 ▶). For a related structure, see: Liu et al. (2010 ▶).

Experimental

Crystal data

[CdCl2(C12H18N4O2)2]·H2O

M = 701.92

Monoclinic,

a = 15.3629 (13) Å

b = 11.0659 (9) Å

c = 18.4492 (16) Å

β = 102.558 (1)°

V = 3061.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.94 mm−1

T = 293 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.793, T max = 0.835

21862 measured reflections

5691 independent reflections

4148 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.087

S = 1.04

5691 reflections

372 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019148/rz2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019148/rz2451Isup2.hkl

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

[CdCl2(C12H18N4O2)2]·H2O	F(000) = 1440
Mr = 701.92	Dx = 1.523 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9598 reflections
a = 15.3629 (13) Å	θ = 2.2–27.2°
b = 11.0659 (9) Å	µ = 0.94 mm−1
c = 18.4492 (16) Å	T = 293 K
β = 102.558 (1)°	Block, colorless
V = 3061.4 (4) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	5691 independent reflections
Radiation source: sealed tube	4148 reflections with I > 2σ(I)
graphite	Rint = 0.022
phi and ω scans	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→18
Tmin = 0.793, Tmax = 0.835	k = −13→13
21862 measured reflections	l = −22→22

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0331P)2 + 3.6911P] where P = (Fo2 + 2Fc2)/3
5691 reflections	(Δ/σ)max < 0.001
372 parameters	Δρmax = 0.53 e Å−3
8 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cd1	0.5000	0.0000	0.5000	0.03408 (9)
Cd2	0.0000	0.5000	0.5000	0.03731 (10)
Cl1	0.35374 (6)	0.07994 (8)	0.40345 (5)	0.0623 (3)
Cl2	−0.14291 (6)	0.51856 (10)	0.38908 (5)	0.0654 (3)
N1	0.06622 (17)	0.6671 (2)	0.45294 (15)	0.0453 (6)
N2	0.1595 (2)	0.7621 (3)	0.39710 (16)	0.0555 (7)
N3	0.0872 (3)	0.2692 (3)	0.3298 (2)	0.0799 (11)
N4	0.06263 (18)	0.3669 (3)	0.42699 (17)	0.0508 (7)
N5	0.58186 (17)	0.1608 (2)	0.46622 (14)	0.0398 (6)
N6	0.61728 (16)	0.3470 (2)	0.44305 (13)	0.0373 (6)
N7	0.48013 (18)	0.2327 (2)	0.69235 (13)	0.0394 (6)
N8	0.46279 (17)	0.1245 (2)	0.59039 (13)	0.0386 (6)
O1	0.1550 (2)	0.6593 (3)	0.25676 (15)	0.0883 (10)
O2	0.1213 (4)	0.4214 (4)	0.2164 (2)	0.148 (2)
O3	0.60598 (15)	0.42888 (19)	0.70446 (12)	0.0457 (5)
O4	0.62769 (15)	0.51267 (18)	0.56526 (12)	0.0456 (5)
O1W	0.6777 (2)	0.5003 (4)	0.26691 (19)	0.0850 (10)
C1	0.6641 (2)	0.1620 (3)	0.44932 (19)	0.0488 (8)
H1	0.6993	0.0940	0.4476	0.059*
C2	0.6870 (2)	0.2762 (3)	0.43540 (18)	0.0460 (8)
H2	0.7398	0.3012	0.4231	0.055*
C3	0.5561 (2)	0.2744 (3)	0.46206 (16)	0.0392 (7)
H3	0.5021	0.3010	0.4712	0.047*
C4	0.6131 (2)	0.4790 (3)	0.43723 (17)	0.0444 (8)
H4A	0.5515	0.5049	0.4304	0.053*
H4B	0.6348	0.5043	0.3940	0.053*
C5	0.6676 (2)	0.5382 (3)	0.50518 (17)	0.0436 (7)
H5A	0.7281	0.5073	0.5152	0.052*
H5B	0.6697	0.6248	0.4977	0.052*
C6	0.6773 (2)	0.5605 (3)	0.63323 (17)	0.0454 (8)
H6A	0.6921	0.6444	0.6267	0.055*
H6B	0.7324	0.5156	0.6491	0.055*
C7	0.6227 (2)	0.5509 (3)	0.68994 (18)	0.0472 (8)
H7A	0.6538	0.5895	0.7354	0.057*
H7B	0.5666	0.5927	0.6726	0.057*
C8	0.5455 (2)	0.4203 (3)	0.75265 (17)	0.0462 (8)
H8A	0.4913	0.4643	0.7318	0.055*
H8B	0.5720	0.4555	0.8005	0.055*
C9	0.5243 (2)	0.2903 (3)	0.76207 (16)	0.0499 (8)
H9A	0.5791	0.2472	0.7826	0.060*
H9B	0.4860	0.2841	0.7974	0.060*
C10	0.5194 (2)	0.1621 (3)	0.65024 (16)	0.0408 (7)
H10	0.5796	0.1418	0.6618	0.049*
C11	0.3925 (2)	0.2424 (3)	0.65710 (17)	0.0442 (8)
H11	0.3485	0.2863	0.6729	0.053*
C12	0.3827 (2)	0.1752 (3)	0.59443 (17)	0.0416 (7)
H12	0.3296	0.1651	0.5595	0.050*
C13	0.0398 (3)	0.3551 (4)	0.3545 (2)	0.0640 (10)
H13	−0.0041	0.4010	0.3240	0.077*
C14	0.1286 (2)	0.2831 (3)	0.4502 (3)	0.0665 (11)
H14	0.1580	0.2696	0.4991	0.080*
C15	0.1439 (3)	0.2235 (4)	0.3904 (4)	0.0868 (16)
H15	0.1856	0.1624	0.3906	0.104*
C16	0.0786 (4)	0.2352 (6)	0.2505 (3)	0.131 (3)
H16A	0.1019	0.1540	0.2490	0.157*
H16B	0.0156	0.2324	0.2273	0.157*
C17	0.1193 (6)	0.3070 (6)	0.2090 (3)	0.139 (3)
H17A	0.1807	0.2800	0.2169	0.167*
H17B	0.0920	0.2903	0.1575	0.167*
C18	0.1213 (7)	0.5041 (6)	0.1698 (3)	0.153 (3)
H18A	0.0604	0.5098	0.1416	0.184*
H18B	0.1561	0.4735	0.1358	0.184*
C19	0.1489 (4)	0.6200 (5)	0.1849 (3)	0.0984 (16)
H19A	0.1081	0.6730	0.1520	0.118*
H19B	0.2071	0.6290	0.1730	0.118*
C20	0.1985 (3)	0.7675 (4)	0.2759 (2)	0.0749 (12)
H20A	0.1580	0.8338	0.2585	0.090*
H20B	0.2485	0.7738	0.2518	0.090*
C21	0.2309 (3)	0.7774 (4)	0.3559 (2)	0.0711 (11)
H21A	0.2583	0.8561	0.3675	0.085*
H21B	0.2763	0.7166	0.3723	0.085*
C22	0.1212 (3)	0.8467 (3)	0.4339 (2)	0.0635 (10)
H22	0.1321	0.9295	0.4352	0.076*
C23	0.1232 (2)	0.6563 (3)	0.40966 (19)	0.0506 (8)
H23	0.1369	0.5832	0.3899	0.061*
C24	0.0646 (2)	0.7880 (3)	0.4682 (2)	0.0588 (9)
H24	0.0299	0.8241	0.4976	0.071*
H1WA	0.678 (5)	0.550 (6)	0.230 (3)	0.19 (3)*
H1WB	0.7311 (18)	0.505 (5)	0.292 (3)	0.12 (2)*

	U11	U22	U33	U12	U13	U23
Cd1	0.04100 (18)	0.02596 (15)	0.03493 (17)	−0.00286 (12)	0.00747 (13)	−0.00432 (12)
Cd2	0.03589 (17)	0.04115 (18)	0.03550 (17)	−0.00300 (13)	0.00907 (13)	0.00258 (13)
Cl1	0.0565 (5)	0.0578 (5)	0.0629 (5)	0.0116 (4)	−0.0079 (4)	−0.0091 (4)
Cl2	0.0485 (5)	0.0866 (7)	0.0535 (5)	−0.0051 (5)	−0.0056 (4)	0.0107 (5)
N1	0.0415 (15)	0.0459 (15)	0.0483 (15)	−0.0039 (12)	0.0091 (12)	0.0062 (13)
N2	0.0594 (19)	0.0520 (17)	0.0558 (18)	−0.0209 (15)	0.0145 (15)	0.0010 (14)
N3	0.091 (3)	0.061 (2)	0.107 (3)	−0.018 (2)	0.062 (2)	−0.030 (2)
N4	0.0454 (16)	0.0502 (16)	0.0607 (18)	−0.0017 (13)	0.0199 (14)	−0.0053 (14)
N5	0.0420 (14)	0.0334 (13)	0.0442 (14)	−0.0046 (11)	0.0096 (12)	−0.0012 (11)
N6	0.0453 (15)	0.0339 (13)	0.0328 (13)	−0.0049 (11)	0.0086 (11)	0.0011 (10)
N7	0.0552 (17)	0.0327 (13)	0.0325 (13)	−0.0055 (12)	0.0142 (12)	−0.0016 (10)
N8	0.0483 (15)	0.0322 (13)	0.0361 (13)	−0.0023 (11)	0.0112 (12)	−0.0025 (11)
O1	0.111 (2)	0.103 (2)	0.0575 (17)	−0.053 (2)	0.0321 (16)	−0.0108 (16)
O2	0.293 (6)	0.086 (3)	0.085 (3)	−0.037 (3)	0.083 (3)	−0.021 (2)
O3	0.0581 (14)	0.0379 (12)	0.0451 (12)	−0.0010 (10)	0.0197 (11)	−0.0046 (10)
O4	0.0514 (13)	0.0461 (13)	0.0399 (12)	−0.0151 (10)	0.0112 (10)	−0.0070 (10)
O1W	0.0576 (19)	0.133 (3)	0.0605 (19)	0.0083 (19)	0.0039 (16)	−0.016 (2)
C1	0.0482 (19)	0.0413 (18)	0.058 (2)	0.0046 (15)	0.0131 (16)	−0.0043 (16)
C2	0.0413 (18)	0.0467 (18)	0.053 (2)	−0.0050 (15)	0.0175 (15)	−0.0033 (15)
C3	0.0403 (17)	0.0369 (16)	0.0419 (17)	−0.0026 (13)	0.0121 (14)	0.0008 (13)
C4	0.059 (2)	0.0336 (16)	0.0378 (17)	−0.0056 (14)	0.0052 (15)	0.0076 (13)
C5	0.054 (2)	0.0332 (15)	0.0440 (18)	−0.0085 (14)	0.0118 (15)	0.0051 (14)
C6	0.0509 (19)	0.0383 (17)	0.0449 (18)	−0.0109 (15)	0.0057 (15)	−0.0062 (14)
C7	0.054 (2)	0.0383 (17)	0.0477 (19)	−0.0041 (15)	0.0081 (16)	−0.0113 (15)
C8	0.061 (2)	0.0445 (18)	0.0348 (16)	−0.0075 (16)	0.0136 (15)	−0.0097 (14)
C9	0.073 (2)	0.0488 (19)	0.0286 (16)	−0.0135 (17)	0.0135 (15)	−0.0028 (14)
C10	0.0435 (17)	0.0406 (17)	0.0397 (17)	−0.0043 (14)	0.0117 (14)	−0.0021 (14)
C11	0.060 (2)	0.0324 (16)	0.0443 (18)	0.0069 (15)	0.0204 (16)	−0.0002 (14)
C12	0.0473 (18)	0.0330 (16)	0.0422 (17)	0.0031 (14)	0.0049 (14)	0.0038 (13)
C13	0.069 (3)	0.059 (2)	0.068 (3)	−0.004 (2)	0.026 (2)	−0.015 (2)
C14	0.046 (2)	0.053 (2)	0.102 (3)	0.0028 (18)	0.021 (2)	0.006 (2)
C15	0.066 (3)	0.049 (2)	0.162 (5)	−0.003 (2)	0.061 (3)	−0.020 (3)
C16	0.169 (6)	0.119 (5)	0.140 (5)	−0.065 (4)	0.110 (5)	−0.085 (4)
C17	0.235 (8)	0.112 (5)	0.068 (4)	−0.037 (5)	0.028 (4)	−0.029 (3)
C18	0.268 (10)	0.119 (6)	0.057 (3)	−0.041 (6)	0.003 (5)	−0.014 (3)
C19	0.138 (5)	0.107 (4)	0.060 (3)	−0.013 (4)	0.042 (3)	0.001 (3)
C20	0.074 (3)	0.077 (3)	0.080 (3)	−0.019 (2)	0.031 (2)	0.010 (2)
C21	0.066 (3)	0.073 (3)	0.080 (3)	−0.026 (2)	0.028 (2)	0.000 (2)
C22	0.069 (3)	0.043 (2)	0.075 (3)	−0.0130 (19)	0.008 (2)	0.0078 (19)
C23	0.050 (2)	0.0487 (19)	0.055 (2)	−0.0121 (16)	0.0150 (17)	0.0019 (16)
C24	0.058 (2)	0.051 (2)	0.069 (2)	−0.0039 (18)	0.0163 (19)	−0.0040 (18)

Cd1—N8	2.328 (2)	C2—H2	0.9300
Cd1—N8i	2.328 (2)	C3—H3	0.9300
Cd1—N5	2.340 (2)	C4—C5	1.499 (4)
Cd1—N5i	2.340 (2)	C4—H4A	0.9700
Cd1—Cl1	2.6951 (9)	C4—H4B	0.9700
Cd1—Cl1i	2.6952 (9)	C5—H5A	0.9700
Cd2—N4ii	2.339 (3)	C5—H5B	0.9700
Cd2—N4	2.339 (3)	C6—C7	1.480 (4)
Cd2—N1	2.365 (3)	C6—H6A	0.9700
Cd2—N1ii	2.365 (3)	C6—H6B	0.9700
Cd2—Cl2	2.6639 (9)	C7—H7A	0.9700
Cd2—Cl2ii	2.6639 (9)	C7—H7B	0.9700
N1—C23	1.313 (4)	C8—C9	1.493 (4)
N1—C24	1.368 (4)	C8—H8A	0.9700
N2—C23	1.338 (4)	C8—H8B	0.9700
N2—C22	1.363 (5)	C9—H9A	0.9700
N2—C21	1.473 (4)	C9—H9B	0.9700
N3—C13	1.337 (5)	C10—H10	0.9300
N3—C15	1.357 (6)	C11—C12	1.355 (4)
N3—C16	1.487 (6)	C11—H11	0.9300
N4—C13	1.313 (5)	C12—H12	0.9300
N4—C14	1.372 (5)	C13—H13	0.9300
N5—C3	1.315 (4)	C14—C15	1.350 (6)
N5—C1	1.366 (4)	C14—H14	0.9300
N6—C3	1.340 (4)	C15—H15	0.9300
N6—C2	1.360 (4)	C16—C17	1.348 (7)
N6—C4	1.464 (4)	C16—H16A	0.9700
N7—C10	1.335 (4)	C16—H16B	0.9700
N7—C11	1.366 (4)	C17—H17A	0.9700
N7—C9	1.464 (4)	C17—H17B	0.9700
N8—C10	1.316 (4)	C18—C19	1.360 (7)
N8—C12	1.370 (4)	C18—H18A	0.9700
O1—C19	1.378 (5)	C18—H18B	0.9700
O1—C20	1.379 (5)	C19—H19A	0.9700
O2—C18	1.256 (7)	C19—H19B	0.9700
O2—C17	1.273 (7)	C20—C21	1.456 (6)
O3—C7	1.411 (4)	C20—H20A	0.9700
O3—C8	1.422 (4)	C20—H20B	0.9700
O4—C5	1.407 (4)	C21—H21A	0.9700
O4—C6	1.420 (4)	C21—H21B	0.9700
O1W—H1WA	0.88 (6)	C22—C24	1.348 (5)
O1W—H1WB	0.85 (2)	C22—H22	0.9300
C1—C2	1.351 (4)	C23—H23	0.9300
C1—H1	0.9300	C24—H24	0.9300
N8—Cd1—N8i	180.00 (9)	C7—C6—H6B	110.0
N8—Cd1—N5	88.32 (8)	H6A—C6—H6B	108.3
N8i—Cd1—N5	91.68 (8)	O3—C7—C6	110.9 (3)
N8—Cd1—N5i	91.68 (8)	O3—C7—H7A	109.5
N8i—Cd1—N5i	88.32 (8)	C6—C7—H7A	109.5
N5—Cd1—N5i	180.0	O3—C7—H7B	109.5
N8—Cd1—Cl1	88.85 (7)	C6—C7—H7B	109.5
N8i—Cd1—Cl1	91.15 (7)	H7A—C7—H7B	108.0
N5—Cd1—Cl1	89.63 (7)	O3—C8—C9	109.0 (3)
N5i—Cd1—Cl1	90.37 (7)	O3—C8—H8A	109.9
N8—Cd1—Cl1i	91.15 (7)	C9—C8—H8A	109.9
N8i—Cd1—Cl1i	88.85 (7)	O3—C8—H8B	109.9
N5—Cd1—Cl1i	90.37 (7)	C9—C8—H8B	109.9
N5i—Cd1—Cl1i	89.63 (7)	H8A—C8—H8B	108.3
Cl1—Cd1—Cl1i	180.0	N7—C9—C8	112.9 (2)
N4ii—Cd2—N4	179.999 (1)	N7—C9—H9A	109.0
N4ii—Cd2—N1	89.01 (10)	C8—C9—H9A	109.0
N4—Cd2—N1	90.99 (10)	N7—C9—H9B	109.0
N4ii—Cd2—N1ii	90.99 (10)	C8—C9—H9B	109.0
N4—Cd2—N1ii	89.01 (10)	H9A—C9—H9B	107.8
N1—Cd2—N1ii	180.0	N8—C10—N7	111.9 (3)
N4ii—Cd2—Cl2	91.17 (8)	N8—C10—H10	124.1
N4—Cd2—Cl2	88.84 (8)	N7—C10—H10	124.1
N1—Cd2—Cl2	90.36 (7)	C12—C11—N7	106.2 (3)
N1ii—Cd2—Cl2	89.65 (7)	C12—C11—H11	126.9
N4ii—Cd2—Cl2ii	88.83 (8)	N7—C11—H11	126.9
N4—Cd2—Cl2ii	91.17 (8)	C11—C12—N8	109.7 (3)
N1—Cd2—Cl2ii	89.64 (7)	C11—C12—H12	125.2
N1ii—Cd2—Cl2ii	90.35 (7)	N8—C12—H12	125.2
Cl2—Cd2—Cl2ii	179.999 (1)	N4—C13—N3	112.0 (4)
C23—N1—C24	105.0 (3)	N4—C13—H13	124.0
C23—N1—Cd2	123.3 (2)	N3—C13—H13	124.0
C24—N1—Cd2	131.4 (2)	C15—C14—N4	108.9 (4)
C23—N2—C22	105.9 (3)	C15—C14—H14	125.5
C23—N2—C21	125.1 (3)	N4—C14—H14	125.5
C22—N2—C21	128.9 (3)	C14—C15—N3	107.2 (4)
C13—N3—C15	106.5 (4)	C14—C15—H15	126.4
C13—N3—C16	125.2 (5)	N3—C15—H15	126.4
C15—N3—C16	128.3 (5)	C17—C16—N3	117.2 (5)
C13—N4—C14	105.4 (3)	C17—C16—H16A	108.0
C13—N4—Cd2	126.7 (3)	N3—C16—H16A	108.0
C14—N4—Cd2	127.9 (3)	C17—C16—H16B	108.0
C3—N5—C1	105.0 (3)	N3—C16—H16B	108.0
C3—N5—Cd1	124.8 (2)	H16A—C16—H16B	107.3
C1—N5—Cd1	130.2 (2)	O2—C17—C16	121.9 (6)
C3—N6—C2	107.1 (3)	O2—C17—H17A	106.9
C3—N6—C4	126.5 (3)	C16—C17—H17A	106.9
C2—N6—C4	126.2 (3)	O2—C17—H17B	106.9
C10—N7—C11	107.0 (2)	C16—C17—H17B	106.9
C10—N7—C9	125.8 (3)	H17A—C17—H17B	106.7
C11—N7—C9	127.2 (3)	O2—C18—C19	126.4 (5)
C10—N8—C12	105.2 (2)	O2—C18—H18A	105.7
C10—N8—Cd1	124.6 (2)	C19—C18—H18A	105.7
C12—N8—Cd1	130.2 (2)	O2—C18—H18B	105.7
C19—O1—C20	116.7 (3)	C19—C18—H18B	105.7
C18—O2—C17	130.9 (5)	H18A—C18—H18B	106.2
C7—O3—C8	110.7 (2)	C18—C19—O1	116.6 (5)
C5—O4—C6	112.2 (2)	C18—C19—H19A	108.1
H1WA—O1W—H1WB	102 (6)	O1—C19—H19A	108.1
C2—C1—N5	110.1 (3)	C18—C19—H19B	108.1
C2—C1—H1	124.9	O1—C19—H19B	108.1
N5—C1—H1	124.9	H19A—C19—H19B	107.3
C1—C2—N6	106.0 (3)	O1—C20—C21	111.4 (3)
C1—C2—H2	127.0	O1—C20—H20A	109.3
N6—C2—H2	127.0	C21—C20—H20A	109.3
N5—C3—N6	111.7 (3)	O1—C20—H20B	109.3
N5—C3—H3	124.1	C21—C20—H20B	109.3
N6—C3—H3	124.1	H20A—C20—H20B	108.0
N6—C4—C5	111.5 (3)	C20—C21—N2	112.7 (3)
N6—C4—H4A	109.3	C20—C21—H21A	109.1
C5—C4—H4A	109.3	N2—C21—H21A	109.1
N6—C4—H4B	109.3	C20—C21—H21B	109.1
C5—C4—H4B	109.3	N2—C21—H21B	109.1
H4A—C4—H4B	108.0	H21A—C21—H21B	107.8
O4—C5—C4	108.1 (2)	C24—C22—N2	107.1 (3)
O4—C5—H5A	110.1	C24—C22—H22	126.4
C4—C5—H5A	110.1	N2—C22—H22	126.4
O4—C5—H5B	110.1	N1—C23—N2	112.5 (3)
C4—C5—H5B	110.1	N1—C23—H23	123.7
H5A—C5—H5B	108.4	N2—C23—H23	123.7
O4—C6—C7	108.7 (3)	C22—C24—N1	109.4 (3)
O4—C6—H6A	110.0	C22—C24—H24	125.3
C7—C6—H6A	110.0	N1—C24—H24	125.3
O4—C6—H6B	110.0
N4ii—Cd2—N1—C23	173.1 (3)	C5—O4—C6—C7	169.1 (3)
N4—Cd2—N1—C23	−6.9 (3)	C8—O3—C7—C6	−173.5 (3)
Cl2—Cd2—N1—C23	−95.8 (3)	O4—C6—C7—O3	64.0 (3)
Cl2ii—Cd2—N1—C23	84.2 (3)	C7—O3—C8—C9	175.8 (3)
N4ii—Cd2—N1—C24	1.1 (3)	C10—N7—C9—C8	100.1 (4)
N4—Cd2—N1—C24	−178.9 (3)	C11—N7—C9—C8	−78.3 (4)
Cl2—Cd2—N1—C24	92.3 (3)	O3—C8—C9—N7	−62.2 (4)
Cl2ii—Cd2—N1—C24	−87.7 (3)	C12—N8—C10—N7	0.5 (3)
N1—Cd2—N4—C13	−70.7 (3)	Cd1—N8—C10—N7	179.79 (18)
N1ii—Cd2—N4—C13	109.3 (3)	C11—N7—C10—N8	−0.6 (3)
Cl2—Cd2—N4—C13	19.7 (3)	C9—N7—C10—N8	−179.3 (3)
Cl2ii—Cd2—N4—C13	−160.3 (3)	C10—N7—C11—C12	0.4 (3)
N1—Cd2—N4—C14	111.2 (3)	C9—N7—C11—C12	179.1 (3)
N1ii—Cd2—N4—C14	−68.8 (3)	N7—C11—C12—N8	−0.1 (3)
Cl2—Cd2—N4—C14	−158.5 (3)	C10—N8—C12—C11	−0.2 (3)
Cl2ii—Cd2—N4—C14	21.5 (3)	Cd1—N8—C12—C11	−179.4 (2)
N8—Cd1—N5—C3	−40.5 (3)	C14—N4—C13—N3	−0.2 (4)
N8i—Cd1—N5—C3	139.5 (3)	Cd2—N4—C13—N3	−178.7 (2)
Cl1—Cd1—N5—C3	48.4 (2)	C15—N3—C13—N4	−0.1 (5)
Cl1i—Cd1—N5—C3	−131.6 (2)	C16—N3—C13—N4	−178.9 (4)
N8—Cd1—N5—C1	137.2 (3)	C13—N4—C14—C15	0.4 (4)
N8i—Cd1—N5—C1	−42.8 (3)	Cd2—N4—C14—C15	178.8 (2)
Cl1—Cd1—N5—C1	−133.9 (3)	N4—C14—C15—N3	−0.4 (5)
Cl1i—Cd1—N5—C1	46.1 (3)	C13—N3—C15—C14	0.3 (5)
N5—Cd1—N8—C10	−68.9 (2)	C16—N3—C15—C14	179.1 (4)
N5i—Cd1—N8—C10	111.1 (2)	C13—N3—C16—C17	79.4 (8)
Cl1—Cd1—N8—C10	−158.6 (2)	C15—N3—C16—C17	−99.2 (8)
Cl1i—Cd1—N8—C10	21.4 (2)	C18—O2—C17—C16	−147.6 (9)
N5—Cd1—N8—C12	110.1 (2)	N3—C16—C17—O2	−38.2 (12)
N5i—Cd1—N8—C12	−69.9 (2)	C17—O2—C18—C19	−159.6 (9)
Cl1—Cd1—N8—C12	20.5 (2)	O2—C18—C19—O1	−18.3 (14)
Cl1i—Cd1—N8—C12	−159.5 (2)	C20—O1—C19—C18	168.1 (6)
C3—N5—C1—C2	0.2 (4)	C19—O1—C20—C21	−158.1 (4)
Cd1—N5—C1—C2	−177.9 (2)	O1—C20—C21—N2	−55.9 (5)
N5—C1—C2—N6	−0.6 (4)	C23—N2—C21—C20	76.6 (5)
C3—N6—C2—C1	0.8 (4)	C22—N2—C21—C20	−108.3 (5)
C4—N6—C2—C1	176.5 (3)	C23—N2—C22—C24	1.0 (4)
C1—N5—C3—N6	0.4 (3)	C21—N2—C22—C24	−174.8 (4)
Cd1—N5—C3—N6	178.53 (18)	C24—N1—C23—N2	1.0 (4)
C2—N6—C3—N5	−0.8 (3)	Cd2—N1—C23—N2	−172.7 (2)
C4—N6—C3—N5	−176.5 (3)	C22—N2—C23—N1	−1.3 (4)
C3—N6—C4—C5	99.4 (4)	C21—N2—C23—N1	174.7 (3)
C2—N6—C4—C5	−75.5 (4)	N2—C22—C24—N1	−0.4 (4)
C6—O4—C5—C4	177.2 (3)	C23—N1—C24—C22	−0.3 (4)
N6—C4—C5—O4	−66.5 (3)	Cd2—N1—C24—C22	172.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···Cl2iii	0.85 (2)	2.33 (3)	3.165 (3)	164 (5)
O1W—H1WA···Cl1iv	0.88 (6)	2.42 (5)	3.198 (4)	147 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯Cl2i	0.85 (2)	2.33 (3)	3.165 (3)	164 (5)
O1W—H1WA⋯Cl1ii	0.88 (6)	2.42 (5)	3.198 (4)	147 (7)

Symmetry codes: (i) ; (ii) .