Bis[μ-4-(dimethyl-amino)-benzoato]-κO,O':O;κO:O,O'-bis-{aqua-[4-(dimethyl-amino)-benzoato-κO,O'](nicotinamide-κN)cadmium(II)}.

In the centrosymmetric dimeric Cd(II) title compound, [Cd(2)(C(9)H(10)NO(2))(4)(C(6)H(6)N(2)O)(2)(H(2)O)(2)], each seven-coordin-ated Cd(II) atom is chelated by the carboxyl-ate groups of the two 4-(dimethyl-amino)-benzoate (DMAB) anions; the two monomeric units are bridged through the two O atoms of the two carboxyl groups. In the crystal structure, inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π contacts between the pyridine rings [centroid-centroid distance = 3.974 (1) Å] may further stabilize the structure. Weak C-H⋯π inter-actions are also observed.

Related literature

For the applications of transition metal complexes with mol­ecules in biological systems, see: Antolini et al. (1982 ▶). Benzoic acid derivatives such as 4-amino­benzoic acid are used extensively as bifunctional organic ligands in coordination chemistry due to the their various coordination modes, see: Amiraslanov et al. (1979 ▶); Chen & Chen (2002 ▶); Hauptmann et al. (2000 ▶). In pellagra disease, niacin deficiency leads to loss of copper from the body with high serum and urinary copper levels, see: Krishnamachari (1974 ▶). The nicotinic acid derivative N,N-diethyl­nicotinamide (DENA) is an important respiratory stimulant, see: Bigoli et al. (1972 ▶). For structure–function–coordination relationships of the aryl­carboxyl­ate ion in MnII complexes of benzoic acid derivatives, see: Adiwidjaja et al. (1978 ▶); Antsyshkina et al. (1980 ▶); Catterick et al. (1974 ▶); Shnulin et al. (1981 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

[Cd2(C9H10NO2)4(C6H6N2O)2(H2O)2]

M = 1161.83

Triclinic,

a = 9.5453 (2) Å

b = 10.2372 (2) Å

c = 13.5697 (3) Å

α = 74.102 (3)°

β = 79.479 (3)°

γ = 66.547 (2)°

V = 1165.85 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.99 mm−1

T = 100 K

0.36 × 0.24 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.752, T max = 0.879

21249 measured reflections

5862 independent reflections

5498 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.056

S = 1.06

5862 reflections

328 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002163X/xu2771sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002163X/xu2771Isup2.hkl

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

[Cd2(C9H10NO2)4(C6H6N2O)2(H2O)2]	Z = 1
Mr = 1161.83	F(000) = 592
Triclinic, P1	Dx = 1.655 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5453 (2) Å	Cell parameters from 9880 reflections
b = 10.2372 (2) Å	θ = 2.4–28.5°
c = 13.5697 (3) Å	µ = 0.99 mm−1
α = 74.102 (3)°	T = 100 K
β = 79.479 (3)°	Block, colorless
γ = 66.547 (2)°	0.36 × 0.24 × 0.13 mm
V = 1165.85 (5) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	5862 independent reflections
Radiation source: fine-focus sealed tube	5498 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.752, Tmax = 0.879	k = −13→13
21249 measured reflections	l = −18→18

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0271P)2 + 0.7237P] where P = (Fo2 + 2Fc2)/3
5862 reflections	(Δ/σ)max < 0.001
328 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.49 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
Cd1	0.180220 (12)	0.040917 (12)	0.492667 (9)	0.01404 (4)
O1	0.10108 (14)	0.14484 (13)	0.63748 (9)	0.0207 (2)
O2	0.33823 (14)	−0.01006 (15)	0.62185 (10)	0.0221 (3)
O3	0.02478 (14)	0.30555 (14)	0.40644 (10)	0.0212 (2)
O4	−0.02665 (13)	0.11559 (13)	0.40059 (9)	0.0189 (2)
O5	0.35463 (15)	−0.60232 (14)	0.34334 (13)	0.0320 (3)
O6	0.34839 (15)	0.12770 (14)	0.37393 (10)	0.0208 (3)
H61	0.438 (3)	0.091 (3)	0.374 (2)	0.039 (7)*
H62	0.331 (3)	0.215 (3)	0.364 (2)	0.042 (7)*
N1	0.2767 (2)	−0.0371 (2)	1.10325 (13)	0.0338 (4)
N2	−0.2931 (2)	0.5498 (2)	−0.01791 (15)	0.0481 (6)
N3	0.32213 (15)	−0.17835 (15)	0.44145 (11)	0.0161 (3)
N4	0.12133 (18)	−0.45388 (19)	0.38859 (17)	0.0367 (5)
H4A	0.0796	−0.5110	0.3814	0.044*
H4B	0.0655	−0.3738	0.4075	0.044*
C1	0.22674 (19)	0.06515 (18)	0.67584 (13)	0.0172 (3)
C2	0.24275 (19)	0.04966 (19)	0.78525 (13)	0.0188 (3)
C3	0.1236 (2)	0.1251 (2)	0.84793 (15)	0.0297 (4)
H3	0.0358	0.1959	0.8188	0.036*
C4	0.1318 (2)	0.0978 (3)	0.95279 (15)	0.0358 (5)
H4	0.0498	0.1506	0.9925	0.043*
C5	0.2614 (2)	−0.0079 (2)	1.00013 (14)	0.0241 (4)
C6	0.3803 (2)	−0.0844 (3)	0.93693 (17)	0.0432 (6)
H6	0.4680	−0.1559	0.9658	0.052*
C7	0.3707 (2)	−0.0565 (3)	0.83278 (17)	0.0414 (6)
H7	0.4520	−0.1101	0.7930	0.050*
C8	0.1518 (3)	0.0277 (3)	1.17494 (18)	0.0522 (7)
H8A	0.1926	0.0409	1.2296	0.078*
H8B	0.0955	−0.0355	1.2029	0.078*
H8C	0.0849	0.1207	1.1397	0.078*
C9	0.4091 (3)	−0.1524 (3)	1.14836 (17)	0.0412 (5)
H9A	0.4063	−0.1499	1.2189	0.062*
H9B	0.5002	−0.1395	1.1114	0.062*
H9C	0.4092	−0.2449	1.1449	0.062*
C10	−0.04015 (17)	0.25041 (18)	0.36627 (13)	0.0164 (3)
C11	−0.12533 (19)	0.33661 (18)	0.27396 (13)	0.0188 (3)
C12	−0.1946 (2)	0.2771 (2)	0.22633 (16)	0.0303 (4)
H12	−0.2022	0.1873	0.2590	0.036*
C13	−0.2528 (3)	0.3473 (3)	0.13181 (18)	0.0400 (5)
H13	−0.2986	0.3040	0.1022	0.048*
C14	−0.2439 (2)	0.4826 (3)	0.07997 (16)	0.0353 (5)
C15	−0.1832 (2)	0.5474 (2)	0.13103 (16)	0.0316 (4)
H15	−0.1824	0.6404	0.1010	0.038*
C16	−0.1245 (2)	0.4756 (2)	0.22524 (14)	0.0231 (4)
H16	−0.0835	0.5207	0.2569	0.028*
C17	−0.2400 (3)	0.6651 (4)	−0.07824 (19)	0.0612 (9)
H17A	−0.2756	0.6970	−0.1457	0.092*
H17B	−0.1300	0.6285	−0.0838	0.092*
H17C	−0.2792	0.7458	−0.0451	0.092*
C18	−0.3162 (4)	0.4603 (4)	−0.0761 (2)	0.0700 (11)
H18A	−0.3484	0.5187	−0.1424	0.105*
H18B	−0.3935	0.4231	−0.0396	0.105*
H18C	−0.2219	0.3802	−0.0846	0.105*
C19	0.25695 (18)	−0.26001 (17)	0.41870 (12)	0.0158 (3)
H19	0.1506	−0.2288	0.4251	0.019*
C20	0.34143 (18)	−0.38911 (17)	0.38596 (13)	0.0160 (3)
C21	0.50027 (19)	−0.43196 (18)	0.37210 (14)	0.0192 (3)
H21	0.5599	−0.5158	0.3479	0.023*
C22	0.56831 (19)	−0.34787 (18)	0.39492 (14)	0.0200 (3)
H22	0.6742	−0.3742	0.3861	0.024*
C23	0.47585 (18)	−0.22380 (18)	0.43116 (13)	0.0183 (3)
H23	0.5221	−0.1699	0.4491	0.022*
C24	0.27089 (19)	−0.48910 (18)	0.37050 (13)	0.0180 (3)

	U11	U22	U33	U12	U13	U23
Cd1	0.00975 (6)	0.01423 (6)	0.01936 (7)	−0.00424 (4)	−0.00041 (4)	−0.00645 (4)
O1	0.0180 (6)	0.0199 (6)	0.0216 (6)	−0.0039 (5)	−0.0013 (5)	−0.0055 (5)
O2	0.0146 (6)	0.0317 (7)	0.0235 (6)	−0.0076 (5)	0.0011 (5)	−0.0147 (5)
O3	0.0175 (6)	0.0234 (6)	0.0251 (6)	−0.0106 (5)	−0.0027 (5)	−0.0038 (5)
O4	0.0146 (5)	0.0156 (5)	0.0242 (6)	−0.0040 (4)	−0.0016 (5)	−0.0032 (5)
O5	0.0226 (7)	0.0207 (6)	0.0575 (10)	−0.0107 (5)	0.0111 (6)	−0.0216 (6)
O6	0.0140 (6)	0.0149 (6)	0.0319 (7)	−0.0055 (5)	0.0024 (5)	−0.0054 (5)
N1	0.0317 (9)	0.0417 (10)	0.0189 (8)	−0.0081 (8)	0.0012 (7)	−0.0031 (7)
N2	0.0338 (10)	0.0590 (14)	0.0280 (10)	0.0090 (9)	−0.0135 (8)	−0.0055 (9)
N3	0.0130 (6)	0.0142 (6)	0.0208 (7)	−0.0052 (5)	0.0000 (5)	−0.0043 (5)
N4	0.0140 (7)	0.0274 (8)	0.0800 (14)	−0.0064 (6)	0.0000 (8)	−0.0343 (9)
C1	0.0168 (7)	0.0183 (7)	0.0206 (8)	−0.0100 (6)	0.0016 (6)	−0.0075 (6)
C2	0.0173 (8)	0.0225 (8)	0.0199 (8)	−0.0098 (7)	0.0013 (6)	−0.0077 (6)
C3	0.0241 (9)	0.0290 (10)	0.0219 (9)	0.0031 (8)	0.0010 (7)	−0.0050 (7)
C4	0.0273 (10)	0.0416 (12)	0.0205 (9)	0.0025 (9)	0.0055 (8)	−0.0067 (8)
C5	0.0227 (9)	0.0290 (9)	0.0204 (8)	−0.0116 (7)	0.0015 (7)	−0.0040 (7)
C6	0.0231 (10)	0.0654 (16)	0.0308 (11)	0.0066 (10)	−0.0103 (8)	−0.0243 (11)
C7	0.0182 (9)	0.0676 (16)	0.0304 (11)	0.0054 (10)	−0.0056 (8)	−0.0284 (11)
C8	0.0413 (14)	0.0785 (19)	0.0211 (10)	−0.0141 (13)	0.0112 (9)	−0.0075 (11)
C9	0.0452 (13)	0.0485 (13)	0.0272 (10)	−0.0092 (11)	−0.0155 (9)	−0.0083 (10)
C10	0.0094 (7)	0.0177 (7)	0.0194 (8)	−0.0030 (6)	0.0010 (6)	−0.0045 (6)
C11	0.0132 (7)	0.0172 (7)	0.0217 (8)	0.0000 (6)	−0.0023 (6)	−0.0054 (6)
C12	0.0327 (10)	0.0223 (9)	0.0367 (11)	−0.0064 (8)	−0.0141 (8)	−0.0060 (8)
C13	0.0404 (12)	0.0380 (12)	0.0417 (12)	−0.0030 (10)	−0.0223 (10)	−0.0141 (10)
C14	0.0227 (9)	0.0399 (11)	0.0263 (10)	0.0078 (8)	−0.0082 (8)	−0.0061 (8)
C15	0.0222 (9)	0.0298 (10)	0.0290 (10)	−0.0014 (8)	−0.0015 (8)	0.0023 (8)
C16	0.0169 (8)	0.0226 (8)	0.0262 (9)	−0.0050 (7)	−0.0004 (7)	−0.0039 (7)
C17	0.0276 (12)	0.083 (2)	0.0278 (12)	0.0100 (12)	−0.0016 (9)	0.0126 (12)
C18	0.0556 (17)	0.085 (2)	0.0421 (15)	0.0227 (16)	−0.0289 (13)	−0.0291 (15)
C19	0.0124 (7)	0.0151 (7)	0.0199 (8)	−0.0058 (6)	0.0002 (6)	−0.0040 (6)
C20	0.0143 (7)	0.0138 (7)	0.0199 (8)	−0.0053 (6)	−0.0002 (6)	−0.0043 (6)
C21	0.0136 (7)	0.0155 (7)	0.0257 (8)	−0.0032 (6)	0.0017 (6)	−0.0058 (6)
C22	0.0106 (7)	0.0176 (8)	0.0293 (9)	−0.0042 (6)	0.0002 (6)	−0.0038 (7)
C23	0.0139 (7)	0.0169 (7)	0.0248 (8)	−0.0072 (6)	−0.0011 (6)	−0.0038 (6)
C24	0.0164 (7)	0.0141 (7)	0.0236 (8)	−0.0057 (6)	−0.0010 (6)	−0.0045 (6)

Cd1—O1	2.3511 (12)	C8—H8A	0.9600
Cd1—O2	2.3362 (12)	C8—H8B	0.9600
Cd1—O3	2.5705 (13)	C8—H8C	0.9600
Cd1—O4i	2.5762 (12)	C9—H9A	0.9600
Cd1—O6	2.3170 (12)	C9—H9B	0.9600
Cd1—N3	2.3339 (14)	C9—H9C	0.9600
Cd1—C1	2.6955 (17)	C11—C10	1.485 (2)
O1—C1	1.262 (2)	C11—C12	1.385 (3)
O2—C1	1.278 (2)	C11—C16	1.398 (2)
O3—C10	1.253 (2)	C12—C13	1.381 (3)
O4—Cd1	2.2849 (12)	C12—H12	0.9300
O4—Cd1i	2.5762 (12)	C13—C14	1.400 (3)
O4—C10	1.291 (2)	C13—H13	0.9300
O5—C24	1.228 (2)	C14—N2	1.388 (3)
O6—H61	0.78 (3)	C15—C14	1.400 (3)
O6—H62	0.81 (3)	C15—H15	0.9300
N1—C5	1.371 (2)	C16—C15	1.381 (3)
N1—C8	1.452 (3)	C16—H16	0.9300
N1—C9	1.437 (3)	C17—N2	1.455 (4)
N3—C19	1.344 (2)	C17—H17A	0.9600
N3—C23	1.344 (2)	C17—H17B	0.9600
N4—C24	1.319 (2)	C17—H17C	0.9600
N4—H4A	0.8600	C18—N2	1.460 (4)
N4—H4B	0.8600	C18—H18A	0.9600
C1—C2	1.479 (2)	C18—H18B	0.9600
C2—C3	1.386 (2)	C18—H18C	0.9600
C2—C7	1.391 (3)	C19—C20	1.392 (2)
C3—C4	1.384 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.392 (2)
C4—H4	0.9300	C20—C24	1.504 (2)
C5—C4	1.399 (3)	C21—C22	1.387 (2)
C5—C6	1.394 (3)	C21—H21	0.9300
C6—C7	1.376 (3)	C22—H22	0.9300
C6—H6	0.9300	C23—C22	1.388 (2)
C7—H7	0.9300	C23—H23	0.9300
O1—Cd1—O3	80.40 (4)	C7—C6—C5	121.4 (2)
O1—Cd1—O4i	81.03 (4)	C7—C6—H6	119.3
O1—Cd1—C1	27.90 (5)	C2—C7—H7	119.1
O2—Cd1—O1	55.96 (4)	C6—C7—C2	121.85 (19)
O2—Cd1—O3	121.05 (4)	C6—C7—H7	119.1
O2—Cd1—O4i	95.15 (4)	N1—C8—H8A	109.5
O2—Cd1—C1	28.30 (5)	N1—C8—H8B	109.5
O3—Cd1—O4i	116.80 (4)	N1—C8—H8C	109.5
O3—Cd1—C1	103.06 (5)	H8A—C8—H8B	109.5
O4—Cd1—O1	108.51 (4)	H8A—C8—H8C	109.5
O4—Cd1—O2	163.91 (4)	H8B—C8—H8C	109.5
O4—Cd1—O3	53.78 (4)	N1—C9—H9A	109.5
O4—Cd1—O4i	76.87 (4)	N1—C9—H9B	109.5
O4—Cd1—O6	102.15 (5)	N1—C9—H9C	109.5
O4—Cd1—N3	98.43 (5)	H9A—C9—H9B	109.5
O4—Cd1—C1	135.79 (5)	H9A—C9—H9C	109.5
O4i—Cd1—C1	85.18 (4)	H9B—C9—H9C	109.5
O6—Cd1—O1	113.98 (5)	O3—C10—O4	120.68 (15)
O6—Cd1—O2	89.36 (5)	O3—C10—C11	120.28 (15)
O6—Cd1—O3	73.12 (4)	O4—C10—C11	118.91 (15)
O6—Cd1—O4i	163.97 (4)	C12—C11—C10	121.50 (16)
O6—Cd1—N3	84.01 (5)	C12—C11—C16	117.17 (17)
O6—Cd1—C1	105.44 (5)	C16—C11—C10	120.97 (16)
N3—Cd1—O1	142.57 (5)	C11—C12—H12	119.0
N3—Cd1—O2	93.88 (5)	C13—C12—C11	121.9 (2)
N3—Cd1—O3	137.02 (4)	C13—C12—H12	119.0
N3—Cd1—O4i	80.34 (4)	C12—C13—C14	121.0 (2)
N3—Cd1—C1	118.10 (5)	C12—C13—H13	119.5
C1—O1—Cd1	91.41 (10)	C14—C13—H13	119.5
C1—O2—Cd1	91.67 (10)	N2—C14—C13	121.5 (2)
C10—O3—Cd1	85.54 (10)	N2—C14—C15	121.4 (2)
Cd1—O4—Cd1i	103.13 (4)	C13—C14—C15	117.13 (18)
C10—O4—Cd1	97.69 (10)	C14—C15—H15	119.4
C10—O4—Cd1i	140.80 (10)	C16—C15—C14	121.2 (2)
Cd1—O6—H61	124 (2)	C16—C15—H15	119.4
Cd1—O6—H62	116.2 (19)	C11—C16—H16	119.3
H61—O6—H62	104 (3)	C15—C16—C11	121.40 (19)
C5—N1—C9	120.90 (18)	C15—C16—H16	119.3
C5—N1—C8	122.36 (19)	N2—C17—H17A	109.5
C9—N1—C8	115.94 (18)	N2—C17—H17B	109.5
C14—N2—C17	117.8 (2)	N2—C17—H17C	109.5
C14—N2—C18	117.6 (2)	H17A—C17—H17B	109.5
C17—N2—C18	115.8 (2)	H17A—C17—H17C	109.5
C19—N3—Cd1	122.92 (10)	H17B—C17—H17C	109.5
C23—N3—Cd1	119.01 (11)	N2—C18—H18A	109.5
C23—N3—C19	118.04 (14)	N2—C18—H18B	109.5
C24—N4—H4A	120.0	N2—C18—H18C	109.5
C24—N4—H4B	120.0	H18A—C18—H18B	109.5
H4A—N4—H4B	120.0	H18A—C18—H18C	109.5
O1—C1—Cd1	60.69 (9)	H18B—C18—H18C	109.5
O1—C1—O2	119.93 (15)	N3—C19—C20	122.96 (14)
O1—C1—C2	120.45 (15)	N3—C19—H19	118.5
O2—C1—Cd1	60.04 (9)	C20—C19—H19	118.5
O2—C1—C2	119.48 (15)	C19—C20—C21	118.29 (15)
C2—C1—Cd1	167.27 (11)	C19—C20—C24	123.42 (14)
C3—C2—C1	121.73 (16)	C21—C20—C24	118.20 (14)
C3—C2—C7	116.93 (17)	C20—C21—H21	120.5
C7—C2—C1	120.76 (16)	C22—C21—C20	119.03 (15)
C2—C3—H3	119.1	C22—C21—H21	120.5
C4—C3—C2	121.74 (18)	C21—C22—C23	118.92 (15)
C4—C3—H3	119.1	C21—C22—H22	120.5
C3—C4—C5	121.17 (18)	C23—C22—H22	120.5
C3—C4—H4	119.4	N3—C23—C22	122.66 (15)
C5—C4—H4	119.4	N3—C23—H23	118.7
N1—C5—C4	123.52 (18)	C22—C23—H23	118.7
N1—C5—C6	119.59 (18)	O5—C24—N4	122.03 (16)
C6—C5—C4	116.89 (18)	O5—C24—C20	118.99 (15)
C5—C6—H6	119.3	N4—C24—C20	118.97 (15)
O2—Cd1—O1—C1	−5.81 (9)	Cd1i—O4—Cd1—C1	−68.68 (7)
O3—Cd1—O1—C1	−144.01 (10)	C10—O4—Cd1—O1	70.86 (10)
O4—Cd1—O1—C1	169.50 (9)	C10—O4—Cd1—O2	85.00 (18)
O4i—Cd1—O1—C1	96.68 (10)	C10—O4—Cd1—O3	8.44 (9)
O6—Cd1—O1—C1	−77.44 (10)	C10—O4—Cd1—O4i	146.56 (11)
N3—Cd1—O1—C1	35.73 (13)	C10—O4—Cd1—O6	−49.84 (10)
O1—Cd1—O2—C1	5.74 (9)	C10—O4—Cd1—N3	−135.48 (10)
O3—Cd1—O2—C1	55.83 (11)	C10—O4—Cd1—C1	77.88 (11)
O4—Cd1—O2—C1	−10.5 (2)	Cd1—O4—C10—O3	−16.40 (16)
O4i—Cd1—O2—C1	−69.80 (10)	Cd1i—O4—C10—O3	105.49 (18)
O6—Cd1—O2—C1	125.61 (10)	Cd1—O4—C10—C11	159.57 (12)
N3—Cd1—O2—C1	−150.44 (10)	Cd1i—O4—C10—C11	−78.5 (2)
O1—Cd1—O3—C10	−130.16 (10)	C8—N1—C5—C4	7.3 (4)
O2—Cd1—O3—C10	−170.30 (9)	C8—N1—C5—C6	−173.6 (3)
O4—Cd1—O3—C10	−8.64 (9)	C9—N1—C5—C4	176.6 (2)
O4i—Cd1—O3—C10	−55.38 (10)	C9—N1—C5—C6	−4.3 (3)
O6—Cd1—O3—C10	111.01 (10)	Cd1—N3—C19—C20	178.53 (12)
N3—Cd1—O3—C10	50.07 (11)	C23—N3—C19—C20	0.5 (2)
C1—Cd1—O3—C10	−146.56 (9)	Cd1—N3—C23—C22	−175.85 (13)
O1—Cd1—N3—C19	104.17 (13)	C19—N3—C23—C22	2.3 (2)
O1—Cd1—N3—C23	−77.81 (14)	Cd1—C1—C2—C3	−93.7 (6)
O2—Cd1—N3—C19	137.60 (13)	Cd1—C1—C2—C7	77.3 (6)
O2—Cd1—N3—C23	−44.39 (13)	O1—C1—C2—C3	−2.3 (3)
O3—Cd1—N3—C19	−76.20 (14)	O1—C1—C2—C7	168.71 (19)
O3—Cd1—N3—C23	101.82 (13)	O2—C1—C2—C3	−177.86 (17)
O4—Cd1—N3—C19	−32.01 (13)	O2—C1—C2—C7	−6.9 (3)
O4i—Cd1—N3—C19	43.03 (12)	C1—C2—C3—C4	172.1 (2)
O4—Cd1—N3—C23	146.00 (12)	C7—C2—C3—C4	0.8 (3)
O4i—Cd1—N3—C23	−138.96 (13)	C1—C2—C7—C6	−172.4 (2)
O6—Cd1—N3—C19	−133.45 (13)	C3—C2—C7—C6	−1.0 (4)
O6—Cd1—N3—C23	44.56 (12)	C2—C3—C4—C5	−0.1 (4)
C1—Cd1—N3—C19	122.22 (12)	N1—C5—C4—C3	178.6 (2)
C1—Cd1—N3—C23	−59.76 (13)	C6—C5—C4—C3	−0.5 (4)
O1—Cd1—C1—O2	−169.81 (16)	N1—C5—C6—C7	−178.8 (3)
O1—Cd1—C1—C2	98.7 (5)	C4—C5—C6—C7	0.4 (4)
O2—Cd1—C1—O1	169.81 (16)	C5—C6—C7—C2	0.4 (4)
O2—Cd1—C1—C2	−91.5 (5)	C12—C11—C10—O3	178.21 (17)
O3—Cd1—C1—O1	36.50 (10)	C12—C11—C10—O4	2.2 (2)
O3—Cd1—C1—O2	−133.31 (10)	C16—C11—C10—O3	5.3 (2)
O3—Cd1—C1—C2	135.2 (5)	C16—C11—C10—O4	−170.72 (15)
O4—Cd1—C1—O1	−14.35 (13)	C10—C11—C12—C13	−169.52 (19)
O4i—Cd1—C1—O1	−79.92 (9)	C16—C11—C12—C13	3.7 (3)
O4—Cd1—C1—O2	175.84 (9)	C10—C11—C16—C15	170.03 (16)
O4i—Cd1—C1—O2	110.28 (10)	C12—C11—C16—C15	−3.2 (3)
O4—Cd1—C1—C2	84.4 (5)	C11—C12—C13—C14	0.0 (3)
O4i—Cd1—C1—C2	18.8 (5)	C12—C13—C14—N2	175.8 (2)
O6—Cd1—C1—O1	112.31 (10)	C12—C13—C14—C15	−4.1 (3)
O6—Cd1—C1—O2	−57.50 (10)	C13—C14—N2—C17	−162.1 (2)
O6—Cd1—C1—C2	−149.0 (5)	C13—C14—N2—C18	−15.8 (3)
N3—Cd1—C1—O1	−156.28 (9)	C15—C14—N2—C17	17.8 (3)
N3—Cd1—C1—O2	33.92 (11)	C15—C14—N2—C18	164.1 (2)
N3—Cd1—C1—C2	−57.5 (5)	C16—C15—C14—N2	−175.34 (19)
Cd1—O1—C1—O2	10.19 (16)	C16—C15—C14—C13	4.6 (3)
Cd1—O1—C1—C2	−165.37 (13)	C11—C16—C15—C14	−1.0 (3)
Cd1—O2—C1—O1	−10.26 (16)	N3—C19—C20—C21	−2.8 (2)
Cd1—O2—C1—C2	165.34 (13)	N3—C19—C20—C24	173.63 (15)
Cd1—O3—C10—O4	14.44 (14)	C19—C20—C21—C22	2.3 (2)
Cd1—O3—C10—C11	−161.46 (14)	C24—C20—C21—C22	−174.27 (16)
Cd1i—O4—Cd1—O1	−75.71 (5)	C19—C20—C24—O5	−178.59 (17)
Cd1i—O4—Cd1—O2	−61.56 (17)	C19—C20—C24—N4	0.0 (3)
Cd1i—O4—Cd1—O3	−138.13 (6)	C21—C20—C24—O5	−2.2 (3)
Cd1i—O4—Cd1—O4i	0.0	C21—C20—C24—N4	176.46 (18)
Cd1i—O4—Cd1—O6	163.60 (4)	C20—C21—C22—C23	0.2 (3)
Cd1i—O4—Cd1—N3	77.95 (5)	N3—C23—C22—C21	−2.6 (3)

Cg2 and Cg3 are the centroids of the C11–C16 and N3/C19–C23 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O3ii	0.86	2.07	2.893 (2)	160
N4—H4B···O1i	0.86	2.24	2.993 (2)	147
O6—H61···O2iii	0.79 (3)	1.97 (3)	2.749 (2)	176 (2)
O6—H62···O5iv	0.82 (3)	1.91 (3)	2.703 (2)	163 (3)
C19—H19···O1i	0.93	2.44	3.302 (2)	155
C23—H23···O2iii	0.93	2.57	3.372 (2)	144
C9—H9A···Cg3v	0.96	2.61	3.434 (2)	144
C17—H17B···Cg2vi	0.96	2.98	3.887 (3)	159

Table 1

Selected bond lengths (Å)

Cd1—O1	2.3511 (12)
Cd1—O2	2.3362 (12)
Cd1—O3	2.5705 (13)
Cd1—O4i	2.5762 (12)
Cd1—O6	2.3170 (12)
Cd1—N3	2.3339 (14)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C11–C16 and N3/C19–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O3ii	0.86	2.07	2.893 (2)	160
N4—H4B⋯O1i	0.86	2.24	2.993 (2)	147
O6—H61⋯O2iii	0.79 (3)	1.97 (3)	2.749 (2)	176 (2)
O6—H62⋯O5iv	0.82 (3)	1.91 (3)	2.703 (2)	163 (3)
C19—H19⋯O1i	0.93	2.44	3.302 (2)	155
C23—H23⋯O2iii	0.93	2.57	3.372 (2)	144
C9—H9A⋯Cg3v	0.96	2.61	3.434 (2)	144
C17—H17B⋯Cg2vi	0.96	2.98	3.887 (3)	159

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