Syntheses, supramolecular networks and Hirshfeld surface and thermal analyses of two new cadmium chloride coordination polymers with an N,O-chelating ligand

Two new coordination polymers, namely poly[[(3-amino­pyrazin-4-ium-2-car­box­yl­ate-κ²N¹,O)di-μ-chlorido-cadmium(II)] monohydrate], {[CdCl₂(C₅H₅N₃O₂)]·H₂O}_n, (1), and poly[2-amino-3-carb­oxy­pyrazin-1-ium [(3-amino­pyrazine-2-carboxyl­ato-κ²N¹,O)di-μ-chlorido-cadmium(II)] monohydrate], {(C₅H₆N₃O₂)[Cd(C₅H₄N₃O₂)Cl₂]·H₂O}_n, (2), have been synthesized from the reaction of cadmium(II) chloride and 3-amino­pyrazine-2-carb­oxy­lic acid (Hapca) under mild conditions in acidic media. The two coordination polymers have been characterized by single-crystal X-ray diffraction and show chloride-bridged zigzag chains with octa­hedrally coordinated metal ions, where Hapca acts as a bidentate ligand via the π-conjugated N atom and a carboxyl­ate O atom. The chains are further inter­connected via noncovalent inter­actions into three-dimensional supra­molecular networks. The dominant H...O and H...Cl inter­actions for both compounds were qu­anti­fied using Hirshfeld surface analysis. The thermal stability and topological analysis of the two-dimensional networks of (1) and (2) are also discussed.

Computing details

For both structures, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011); data reduction: APEX2 (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: OTREP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001) for Cd1F; ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001) for Cd1. For both structures, software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Poly[[(3-aminopyrazin-4-ium-2-carboxylate-κ²N¹,O)di-µ-chlorido-cadmium(II)] monohydrate] (Cd1F)

Crystal data

[CdCl2(C5H5N3O2)]·H2O	Z = 2
Mr = 340.45	F(000) = 328
Triclinic, P1	Dx = 2.312 Mg m^−3
a = 6.9452 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8334 (1) Å	Cell parameters from 3266 reflections
c = 9.9918 (2) Å	θ = 2.9–27.5°
α = 98.677 (2)°	µ = 2.76 mm^−1
β = 97.359 (1)°	T = 150 K
γ = 111.725 (1)°	Prism, colourless
V = 489.09 (2) Å^3	0.13 × 0.09 × 0.05 mm

Data collection

Bruker APEXII diffractometer	2032 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→9
Tmin = 0.766, Tmax = 0.871	k = −10→9
6756 measured reflections	l = −12→12
2203 independent 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0159P)^2 + 0.1709P] where P = (Fo^2 + 2Fc^2)/3
2203 reflections	(Δ/σ)max = 0.01
133 parameters	Δρmax = 0.43 e Å^−3
1 restraint	Δρmin = −0.43 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
Cd1	0.73326 (3)	0.51125 (2)	0.922827 (17)	0.01450 (7)
Cl1	1.05140 (9)	0.71338 (8)	1.12053 (6)	0.01625 (13)
Cl2	0.49546 (10)	0.29073 (9)	1.05343 (7)	0.02109 (14)
O1	0.5761 (3)	0.3665 (2)	0.69748 (17)	0.0176 (4)
O1W	0.2860 (3)	0.0316 (3)	0.3913 (2)	0.0255 (4)
H1W	0.290 (5)	−0.025 (4)	0.314 (3)	0.038*
H2W	0.395 (5)	0.127 (4)	0.417 (3)	0.038*
O2	0.6091 (3)	0.3536 (2)	0.47733 (17)	0.0199 (4)
N1	0.9234 (3)	0.6980 (3)	0.7753 (2)	0.0144 (4)
N3	0.8868 (3)	0.6422 (3)	0.4055 (2)	0.0193 (5)
H3A	0.9542	0.7018	0.3491	0.023*
H3B	0.7779	0.5383	0.3743	0.023*
C4	1.1939 (4)	0.9528 (4)	0.7237 (3)	0.0188 (5)
H4	1.3113	1.0664	0.7527	0.023*
N2	1.1220 (3)	0.8737 (3)	0.5885 (2)	0.0170 (5)
H2	1.1879	0.9295	0.53	0.02*
C5	1.0932 (4)	0.8649 (3)	0.8179 (3)	0.0182 (5)
H5	1.1408	0.9195	0.9117	0.022*
C3	0.9508 (4)	0.7104 (3)	0.5403 (2)	0.0157 (5)
C2	0.8506 (4)	0.6202 (3)	0.6426 (2)	0.0137 (5)
C1	0.6623 (4)	0.4311 (3)	0.6033 (2)	0.0149 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.01298 (11)	0.01680 (11)	0.01150 (10)	0.00375 (8)	0.00224 (7)	0.00239 (7)
Cl1	0.0171 (3)	0.0172 (3)	0.0118 (3)	0.0056 (3)	0.0009 (2)	0.0001 (2)
Cl2	0.0203 (3)	0.0212 (3)	0.0272 (3)	0.0098 (3)	0.0109 (3)	0.0115 (3)
O1	0.0157 (9)	0.0184 (9)	0.0139 (9)	0.0010 (8)	0.0027 (7)	0.0044 (7)
O1W	0.0281 (12)	0.0183 (10)	0.0174 (10)	−0.0031 (9)	0.0057 (9)	−0.0019 (8)
O2	0.0211 (10)	0.0176 (9)	0.0121 (9)	−0.0002 (8)	0.0016 (8)	−0.0008 (7)
N1	0.0133 (11)	0.0129 (10)	0.0155 (11)	0.0043 (9)	0.0012 (8)	0.0024 (8)
N3	0.0201 (12)	0.0204 (12)	0.0130 (11)	0.0029 (10)	0.0034 (9)	0.0039 (9)
C4	0.0151 (13)	0.0143 (13)	0.0236 (14)	0.0024 (11)	0.0037 (11)	0.0029 (11)
N2	0.0202 (12)	0.0161 (11)	0.0163 (11)	0.0060 (9)	0.0090 (9)	0.0072 (9)
C5	0.0188 (14)	0.0164 (13)	0.0146 (13)	0.0043 (11)	−0.0005 (10)	−0.0003 (10)
C3	0.0151 (13)	0.0172 (13)	0.0170 (13)	0.0088 (11)	0.0036 (10)	0.0033 (10)
C2	0.0143 (13)	0.0121 (12)	0.0147 (12)	0.0055 (10)	0.0022 (10)	0.0029 (10)
C1	0.0129 (13)	0.0154 (12)	0.0159 (13)	0.0064 (10)	−0.0003 (10)	0.0021 (10)

Geometric parameters (Å, º)

Cd1—O1	2.2871 (17)	N1—C5	1.358 (3)
Cd1—N1	2.403 (2)	N3—C3	1.323 (3)
Cd1—Cl2	2.5563 (7)	N3—H3A	0.86
Cd1—Cl1	2.5768 (6)	N3—H3B	0.86
Cd1—Cl2^i	2.6068 (6)	C4—N2	1.343 (3)
Cd1—Cl1^ii	2.7213 (6)	C4—C5	1.363 (4)
Cl1—Cd1^ii	2.7213 (6)	C4—H4	0.93
Cl2—Cd1^i	2.6068 (6)	N2—C3	1.350 (3)
O1—C1	1.250 (3)	N2—H2	0.86
O1W—H1W	0.84 (3)	C5—H5	0.93
O1W—H2W	0.82 (3)	C3—C2	1.437 (3)
O2—C1	1.254 (3)	C2—C1	1.523 (3)
N1—C2	1.319 (3)
O1—Cd1—N1	71.07 (6)	C3—N3—H3A	120
O1—Cd1—Cl2	102.10 (5)	C3—N3—H3B	120
N1—Cd1—Cl2	172.98 (5)	H3A—N3—H3B	120
O1—Cd1—Cl1	154.04 (5)	N2—C4—C5	119.3 (2)
N1—Cd1—Cl1	86.75 (5)	N2—C4—H4	120.3
Cl2—Cd1—Cl1	100.27 (2)	C5—C4—H4	120.3
O1—Cd1—Cl2^i	94.40 (5)	C4—N2—C3	122.9 (2)
N1—Cd1—Cl2^i	91.13 (5)	C4—N2—H2	118.5
Cl2—Cd1—Cl2^i	87.78 (2)	C3—N2—H2	118.5
Cl1—Cd1—Cl2^i	99.49 (2)	N1—C5—C4	120.2 (2)
O1—Cd1—Cl1^ii	81.18 (4)	N1—C5—H5	119.9
N1—Cd1—Cl1^ii	88.69 (5)	C4—C5—H5	119.9
Cl2—Cd1—Cl1^ii	91.839 (19)	N3—C3—N2	119.6 (2)
Cl1—Cd1—Cl1^ii	85.113 (19)	N3—C3—C2	124.1 (2)
Cl2^i—Cd1—Cl1^ii	175.38 (2)	N2—C3—C2	116.2 (2)
Cd1—Cl1—Cd1^ii	94.887 (19)	N1—C2—C3	120.5 (2)
Cd1—Cl2—Cd1^i	92.22 (2)	N1—C2—C1	117.7 (2)
C1—O1—Cd1	119.29 (16)	C3—C2—C1	121.8 (2)
H1W—O1W—H2W	108 (3)	O1—C1—O2	126.0 (2)
C2—N1—C5	120.8 (2)	O1—C1—C2	118.1 (2)
C2—N1—Cd1	113.27 (16)	O2—C1—C2	115.9 (2)
C5—N1—Cd1	125.87 (16)
O1—Cd1—Cl1—Cd1^ii	−58.18 (10)	Cl1^ii—Cd1—N1—C5	−100.49 (18)
N1—Cd1—Cl1—Cd1^ii	−88.96 (5)	C5—C4—N2—C3	0.9 (4)
Cl2—Cd1—Cl1—Cd1^ii	90.99 (2)	C2—N1—C5—C4	−1.4 (3)
Cl2^i—Cd1—Cl1—Cd1^ii	−179.566 (18)	Cd1—N1—C5—C4	176.69 (17)
Cl1^ii—Cd1—Cl1—Cd1^ii	0	N2—C4—C5—N1	0.8 (4)
O1—Cd1—Cl2—Cd1^i	−94.02 (5)	C4—N2—C3—N3	178.9 (2)
Cl1—Cd1—Cl2—Cd1^i	99.24 (2)	C4—N2—C3—C2	−1.8 (3)
Cl2^i—Cd1—Cl2—Cd1^i	0	C5—N1—C2—C3	0.4 (3)
Cl1^ii—Cd1—Cl2—Cd1^i	−175.39 (2)	Cd1—N1—C2—C3	−177.91 (16)
N1—Cd1—O1—C1	6.80 (16)	C5—N1—C2—C1	178.8 (2)
Cl2—Cd1—O1—C1	−174.84 (16)	Cd1—N1—C2—C1	0.5 (2)
Cl1—Cd1—O1—C1	−25.9 (2)	N3—C3—C2—N1	−179.6 (2)
Cl2^i—Cd1—O1—C1	96.49 (16)	N2—C3—C2—N1	1.2 (3)
Cl1^ii—Cd1—O1—C1	−84.84 (16)	N3—C3—C2—C1	2.1 (4)
O1—Cd1—N1—C2	−3.36 (15)	N2—C3—C2—C1	−177.17 (19)
Cl1—Cd1—N1—C2	162.94 (16)	Cd1—O1—C1—O2	170.44 (18)
Cl2^i—Cd1—N1—C2	−97.62 (15)	Cd1—O1—C1—C2	−9.0 (3)
Cl1^ii—Cd1—N1—C2	77.76 (15)	N1—C2—C1—O1	5.6 (3)
O1—Cd1—N1—C5	178.4 (2)	C3—C2—C1—O1	−176.1 (2)
Cl1—Cd1—N1—C5	−15.32 (18)	N1—C2—C1—O2	−173.9 (2)
Cl2^i—Cd1—N1—C5	84.12 (18)	C3—C2—C1—O2	4.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···Cl1^iii	0.84 (3)	2.48 (3)	3.165 (2)	139 (3)
N2—H2···O1W^iv	0.86	1.79	2.641 (3)	171
O1W—H2W···O2	0.82 (3)	1.79 (3)	2.607 (3)	172 (3)
N3—H3A···Cl1^v	0.86	2.47	3.251 (2)	152
N3—H3B···O2	0.86	2.01	2.639 (3)	129
C4—H4···O1^iv	0.93	2.58	3.418 (3)	150
C5—H5···Cl1	0.93	2.82	3.419 (3)	123

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

Poly[2-amino-3-carboxypyrazin-1-ium [(3-aminopyrazine-2-carboxylato-κ²N¹,O)di-µ-chlorido-cadmium(II)] monohydrate] (Cd1)

Crystal data

(C5H6N3O2)[Cd(C5H4N3O2)Cl2]·H2O	Dx = 2.038 Mg m^−3
Mr = 479.57	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pcab	Cell parameters from 4719 reflections
a = 7.2637 (2) Å	θ = 2.9–27.4°
b = 17.7011 (5) Å	µ = 1.78 mm^−1
c = 24.3144 (5) Å	T = 150 K
V = 3126.24 (14) Å^3	Prism, yellow
Z = 8	0.32 × 0.16 × 0.09 mm
F(000) = 1888

Data collection

Bruker APEXII diffractometer	3071 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS: Sheldrick, 2002)	h = −7→9
Tmin = 0.673, Tmax = 0.852	k = −14→22
14874 measured reflections	l = −30→31
3534 independent 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0581P)^2] where P = (Fo^2 + 2Fc^2)/3
3534 reflections	(Δ/σ)max = 0.044
223 parameters	Δρmax = 0.44 e Å^−3
2 restraints	Δρmin = −0.52 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
Cd1	0.59301 (3)	0.707208 (10)	0.095661 (7)	0.01376 (9)
Cl2	0.78224 (9)	0.79847 (3)	0.03572 (2)	0.01588 (14)
Cl1	0.39472 (9)	0.78584 (3)	0.16052 (3)	0.01766 (15)
O1A	0.6969 (2)	0.61123 (9)	0.04216 (7)	0.0175 (4)
O2A	0.7025 (2)	0.48846 (9)	0.02306 (7)	0.0171 (4)
O2B	0.9146 (3)	0.26294 (11)	0.12133 (8)	0.0239 (5)
O1W	0.7245 (3)	0.18053 (11)	0.22195 (7)	0.0210 (4)
H1W	0.791 (4)	0.1472 (16)	0.2057 (10)	0.025*
H2W	0.769 (4)	0.1809 (15)	0.2545 (8)	0.025*
O1B	0.7794 (3)	0.31984 (9)	0.19271 (7)	0.0203 (4)
H1B	0.7462	0.2766	0.1998	0.031*
N3B	1.0915 (3)	0.34875 (13)	0.04737 (9)	0.0213 (5)
H3B1	1.1535	0.3577	0.0179	0.026*
H3B2	1.0568	0.3035	0.0548	0.026*
N1B	0.9131 (3)	0.45382 (12)	0.16369 (9)	0.0160 (5)
N1A	0.5193 (3)	0.58806 (11)	0.13710 (8)	0.0139 (4)
N2A	0.4076 (3)	0.44513 (12)	0.17066 (9)	0.0162 (5)
N2B	1.1063 (3)	0.47511 (12)	0.06822 (9)	0.0149 (5)
H2B	1.1673	0.4824	0.0384	0.018*
N3A	0.5187 (3)	0.39278 (12)	0.09042 (8)	0.0175 (5)
H3A1	0.4803	0.3496	0.1018	0.021*
H3A2	0.5729	0.3964	0.0591	0.021*
C1B	0.8797 (4)	0.31950 (15)	0.14814 (10)	0.0154 (5)
C4B	1.0695 (4)	0.53453 (16)	0.10111 (11)	0.0170 (6)
H4B	1.1083	0.5828	0.0914	0.02*
C3A	0.4367 (4)	0.57804 (15)	0.18563 (10)	0.0184 (6)
H3A	0.4158	0.6191	0.2087	0.022*
C1A	0.6560 (3)	0.54351 (13)	0.05262 (10)	0.0133 (5)
C3B	0.9747 (4)	0.52307 (14)	0.14880 (10)	0.0175 (5)
H3B	0.9517	0.564	0.1718	0.021*
C5B	1.0501 (4)	0.40408 (14)	0.08079 (10)	0.0147 (5)
C2B	0.9480 (4)	0.39624 (14)	0.13115 (10)	0.0140 (5)
C4A	0.3821 (4)	0.50600 (15)	0.20151 (10)	0.0183 (6)
H4A	0.3248	0.5002	0.2355	0.022*
C5A	0.4942 (4)	0.45445 (13)	0.12153 (9)	0.0132 (5)
C2A	0.5519 (3)	0.52824 (15)	0.10494 (10)	0.0122 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.01352 (14)	0.00993 (12)	0.01783 (12)	−0.00012 (7)	0.00300 (7)	−0.00082 (6)
Cl2	0.0156 (3)	0.0147 (3)	0.0174 (3)	−0.0018 (2)	0.0004 (2)	0.0030 (2)
Cl1	0.0176 (4)	0.0175 (3)	0.0178 (3)	0.0029 (2)	0.0008 (2)	−0.0043 (2)
O1A	0.0209 (11)	0.0107 (8)	0.0209 (9)	−0.0017 (8)	0.0083 (8)	0.0015 (7)
O2A	0.0194 (10)	0.0143 (9)	0.0175 (8)	−0.0001 (8)	0.0032 (7)	−0.0025 (7)
O2B	0.0333 (13)	0.0142 (10)	0.0242 (10)	0.0000 (8)	0.0064 (8)	−0.0019 (8)
O1W	0.0276 (12)	0.0172 (9)	0.0181 (9)	0.0019 (9)	0.0011 (8)	−0.0016 (7)
O1B	0.0260 (11)	0.0136 (8)	0.0214 (9)	−0.0024 (8)	0.0080 (8)	0.0016 (7)
N3B	0.0280 (14)	0.0172 (11)	0.0186 (11)	−0.0031 (10)	0.0076 (9)	−0.0036 (9)
N1B	0.0140 (12)	0.0142 (11)	0.0197 (11)	0.0026 (9)	−0.0027 (8)	−0.0013 (8)
N1A	0.0119 (11)	0.0136 (10)	0.0162 (10)	0.0000 (9)	−0.0025 (9)	−0.0012 (8)
N2A	0.0172 (12)	0.0148 (11)	0.0167 (10)	0.0003 (9)	−0.0010 (8)	0.0026 (8)
N2B	0.0120 (11)	0.0151 (11)	0.0176 (11)	−0.0001 (9)	0.0002 (8)	0.0036 (8)
N3A	0.0224 (13)	0.0104 (10)	0.0196 (11)	−0.0020 (10)	0.0024 (9)	−0.0004 (8)
C1B	0.0129 (13)	0.0163 (12)	0.0168 (12)	0.0009 (11)	−0.0023 (10)	0.0002 (10)
C4B	0.0138 (14)	0.0108 (13)	0.0265 (14)	−0.0016 (10)	−0.0045 (10)	0.0022 (10)
C3A	0.0196 (14)	0.0190 (13)	0.0167 (12)	0.0000 (11)	−0.0009 (10)	−0.0025 (10)
C1A	0.0103 (12)	0.0144 (12)	0.0152 (11)	0.0026 (10)	−0.0035 (10)	0.0020 (9)
C3B	0.0189 (14)	0.0108 (12)	0.0229 (13)	0.0007 (11)	0.0002 (11)	−0.0007 (9)
C5B	0.0124 (13)	0.0163 (13)	0.0155 (11)	−0.0022 (11)	−0.0018 (10)	0.0010 (10)
C2B	0.0113 (13)	0.0141 (12)	0.0167 (11)	0.0015 (10)	−0.0015 (10)	0.0004 (9)
C4A	0.0157 (14)	0.0230 (14)	0.0160 (12)	−0.0015 (12)	−0.0001 (10)	0.0021 (10)
C5A	0.0119 (13)	0.0127 (12)	0.0150 (11)	0.0016 (11)	−0.0046 (9)	0.0010 (9)
C2A	0.0081 (12)	0.0146 (12)	0.0140 (11)	0.0006 (10)	−0.0007 (9)	−0.0012 (9)

Geometric parameters (Å, º)

Cd1—O1A	2.2691 (16)	N1A—C3A	1.335 (3)
Cd1—N1A	2.398 (2)	N1A—C2A	1.337 (3)
Cd1—Cl1	2.5493 (6)	N2A—C4A	1.326 (3)
Cd1—Cl2	2.5734 (6)	N2A—C5A	1.360 (3)
Cd1—Cl2^i	2.6888 (7)	N2B—C4B	1.348 (3)
Cd1—Cl1^ii	2.7027 (7)	N2B—C5B	1.357 (3)
Cl2—Cd1^ii	2.6888 (7)	N2B—H2B	0.86
Cl1—Cd1^i	2.7027 (7)	N3A—C5A	1.340 (3)
O1A—C1A	1.261 (3)	N3A—H3A1	0.86
O2A—C1A	1.257 (3)	N3A—H3A2	0.86
O2B—C1B	1.221 (3)	C1B—C2B	1.504 (3)
O1W—H1W	0.86 (3)	C4B—C3B	1.364 (4)
O1W—H2W	0.853 (17)	C4B—H4B	0.93
O1B—C1B	1.306 (3)	C3A—C4A	1.390 (4)
O1B—H1B	0.82	C3A—H3A	0.93
N3B—C5B	1.307 (3)	C1A—C2A	1.504 (3)
N3B—H3B1	0.86	C3B—H3B	0.93
N3B—H3B2	0.86	C5B—C2B	1.438 (4)
N1B—C2B	1.315 (3)	C4A—H4A	0.93
N1B—C3B	1.354 (3)	C5A—C2A	1.430 (3)
O1A—Cd1—N1A	69.92 (6)	C5A—N3A—H3A2	120
O1A—Cd1—Cl1	162.07 (5)	H3A1—N3A—H3A2	120
N1A—Cd1—Cl1	95.40 (5)	O2B—C1B—O1B	124.2 (2)
O1A—Cd1—Cl2	88.14 (4)	O2B—C1B—C2B	121.7 (2)
N1A—Cd1—Cl2	155.42 (5)	O1B—C1B—C2B	114.1 (2)
Cl1—Cd1—Cl2	108.02 (2)	N2B—C4B—C3B	119.2 (2)
O1A—Cd1—Cl2^i	86.59 (5)	N2B—C4B—H4B	120.4
N1A—Cd1—Cl2^i	90.42 (5)	C3B—C4B—H4B	120.4
Cl1—Cd1—Cl2^i	83.18 (2)	N1A—C3A—C4A	119.7 (2)
Cl2—Cd1—Cl2^i	99.49 (2)	N1A—C3A—H3A	120.1
O1A—Cd1—Cl1^ii	95.67 (5)	C4A—C3A—H3A	120.1
N1A—Cd1—Cl1^ii	88.63 (5)	O2A—C1A—O1A	123.9 (2)
Cl1—Cd1—Cl1^ii	94.15 (2)	O2A—C1A—C2A	118.7 (2)
Cl2—Cd1—Cl1^ii	82.46 (2)	O1A—C1A—C2A	117.4 (2)
Cl2^i—Cd1—Cl1^ii	177.07 (2)	N1B—C3B—C4B	121.9 (2)
Cd1—Cl2—Cd1^ii	96.777 (19)	N1B—C3B—H3B	119
Cd1—Cl1—Cd1^i	97.01 (2)	C4B—C3B—H3B	119
C1A—O1A—Cd1	121.17 (15)	N3B—C5B—N2B	119.0 (2)
H1W—O1W—H2W	103 (2)	N3B—C5B—C2B	125.1 (2)
C1B—O1B—H1B	109.5	N2B—C5B—C2B	115.9 (2)
C5B—N3B—H3B1	120	N1B—C2B—C5B	122.5 (2)
C5B—N3B—H3B2	120	N1B—C2B—C1B	118.1 (2)
H3B1—N3B—H3B2	120	C5B—C2B—C1B	119.4 (2)
C2B—N1B—C3B	118.5 (2)	N2A—C4A—C3A	123.2 (2)
C3A—N1A—C2A	119.4 (2)	N2A—C4A—H4A	118.4
C3A—N1A—Cd1	126.04 (17)	C3A—C4A—H4A	118.4
C2A—N1A—Cd1	114.27 (16)	N3A—C5A—N2A	117.3 (2)
C4A—N2A—C5A	117.6 (2)	N3A—C5A—C2A	123.1 (2)
C4B—N2B—C5B	122.0 (2)	N2A—C5A—C2A	119.6 (2)
C4B—N2B—H2B	119	N1A—C2A—C5A	120.4 (2)
C5B—N2B—H2B	119	N1A—C2A—C1A	116.2 (2)
C5A—N3A—H3A1	120	C5A—C2A—C1A	123.4 (2)
O1A—Cd1—Cl2—Cd1^ii	−90.42 (5)	C2B—N1B—C3B—C4B	0.7 (4)
N1A—Cd1—Cl2—Cd1^ii	−64.11 (12)	N2B—C4B—C3B—N1B	−1.3 (4)
Cl1—Cd1—Cl2—Cd1^ii	97.48 (2)	C4B—N2B—C5B—N3B	−179.5 (2)
Cl2^i—Cd1—Cl2—Cd1^ii	−176.654 (19)	C4B—N2B—C5B—C2B	0.4 (4)
Cl1^ii—Cd1—Cl2—Cd1^ii	5.552 (19)	C3B—N1B—C2B—C5B	0.5 (4)
O1A—Cd1—Cl1—Cd1^i	−61.28 (16)	C3B—N1B—C2B—C1B	179.7 (2)
N1A—Cd1—Cl1—Cd1^i	−95.38 (5)	N3B—C5B—C2B—N1B	178.8 (2)
Cl2—Cd1—Cl1—Cd1^i	92.21 (2)	N2B—C5B—C2B—N1B	−1.1 (4)
Cl2^i—Cd1—Cl1—Cd1^i	−5.598 (19)	N3B—C5B—C2B—C1B	−0.4 (4)
Cl1^ii—Cd1—Cl1—Cd1^i	175.62 (2)	N2B—C5B—C2B—C1B	179.8 (2)
N1A—Cd1—O1A—C1A	7.99 (18)	O2B—C1B—C2B—N1B	−176.4 (2)
Cl1—Cd1—O1A—C1A	−28.5 (3)	O1B—C1B—C2B—N1B	4.7 (3)
Cl2—Cd1—O1A—C1A	176.67 (18)	O2B—C1B—C2B—C5B	2.8 (4)
Cl2^i—Cd1—O1A—C1A	−83.71 (18)	O1B—C1B—C2B—C5B	−176.1 (2)
Cl1^ii—Cd1—O1A—C1A	94.44 (18)	C5A—N2A—C4A—C3A	1.0 (4)
O1A—Cd1—N1A—C3A	177.2 (2)	N1A—C3A—C4A—N2A	0.0 (4)
Cl1—Cd1—N1A—C3A	−13.4 (2)	C4A—N2A—C5A—N3A	−179.7 (2)
Cl2—Cd1—N1A—C3A	149.07 (16)	C4A—N2A—C5A—C2A	−0.6 (3)
Cl2^i—Cd1—N1A—C3A	−96.6 (2)	C3A—N1A—C2A—C5A	1.8 (4)
Cl1^ii—Cd1—N1A—C3A	80.7 (2)	Cd1—N1A—C2A—C5A	−172.47 (18)
O1A—Cd1—N1A—C2A	−8.93 (17)	C3A—N1A—C2A—C1A	−176.3 (2)
Cl1—Cd1—N1A—C2A	160.48 (17)	Cd1—N1A—C2A—C1A	9.4 (3)
Cl2—Cd1—N1A—C2A	−37.1 (3)	N3A—C5A—C2A—N1A	178.2 (2)
Cl2^i—Cd1—N1A—C2A	77.28 (17)	N2A—C5A—C2A—N1A	−0.8 (4)
Cl1^ii—Cd1—N1A—C2A	−105.48 (17)	N3A—C5A—C2A—C1A	−3.8 (4)
C5B—N2B—C4B—C3B	0.7 (4)	N2A—C5A—C2A—C1A	177.2 (2)
C2A—N1A—C3A—C4A	−1.5 (4)	O2A—C1A—C2A—N1A	174.6 (2)
Cd1—N1A—C3A—C4A	172.11 (18)	O1A—C1A—C2A—N1A	−2.9 (3)
Cd1—O1A—C1A—O2A	176.64 (18)	O2A—C1A—C2A—C5A	−3.5 (4)
Cd1—O1A—C1A—C2A	−6.0 (3)	O1A—C1A—C2A—C5A	179.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3B—H3B1···O1A^iii	0.86	1.90	2.757 (3)	172
O1B—H1B···O1W	0.82	1.79	2.597 (3)	167
O1W—H1W···N2A^iv	0.86 (3)	2.03 (3)	2.876 (3)	169 (3)
N3B—H3B2···O2B	0.86	2.05	2.682 (3)	130
N2B—H2B···O2A^iii	0.86	1.84	2.696 (3)	172
O1W—H2W···Cl1^v	0.86 (2)	2.34 (2)	3.1701 (19)	166 (2)
N3A—H3A1···O2B^vi	0.86	2.10	2.955 (3)	171
N3A—H3A2···O2A	0.86	2.08	2.708 (3)	130
C3B—H3B···Cl1^ii	0.93	2.70	3.444 (3)	137
C4B—H4B···Cl2^ii	0.93	2.80	3.695 (3)	162

Symmetry codes: (ii) x+1/2, −y+3/2, z; (iii) −x+2, −y+1, −z; (iv) x+1/2, −y+1/2, z; (v) x+1/2, −y+1, −z+1/2; (vi) x−1/2, −y+1/2, z.