Aqua-bis(isonicotinamide-κN)bis-(4-methyl-benzoato)-κO;κO,O'-cadmium(II) monohydrate.

In the crystal structure of the title compound, [Cd(C(8)H(7)O(2))(2)(C(6)H(6)N(2)O)(2)(H(2)O)]·H(2)O, the Cd(II) cation is coordinated by two 4-methyl-benzoate (PMB) anions, two isonicotinamide (INA) ligands and one water mol-ecule in a distorted octa-hedral CdN(2)O(4) geometry. One of PMB ions acts as a bidentate ligand while the other and the two INA are monodentate ligands. An O-H⋯O hydrogen bond links the uncoordinated water mol-ecule to the carboxyl groups of the complex. The dihedral angles between the carboxyl groups and the adjacent benzene rings are 10.28 (11) and 21.24 (9)°, while the two benzene rings and the two pyridine rings are oriented at dihedral angles of 6.90 (4) and 88.64 (4)°, respectively. In the crystal structure, O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular structure. A π-π contact between the benzene rings [centroid-centroid distance = 3.911 (1) Å] may further stabilize the crystal structure. Weak C-H⋯π inter-actions involving the pyridine rings also occur in the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶) and for the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

[Cd(C8H7O2)2(C6H6N2O)2(H2O)]·H2O

M = 662.97

Triclinic,

a = 9.5032 (2) Å

b = 12.3543 (3) Å

c = 13.6134 (3) Å

α = 78.278 (3)°

β = 69.776 (2)°

γ = 71.746 (3)°

V = 1416.18 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.83 mm−1

T = 102 K

0.40 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.819, T max = 0.881

25922 measured reflections

7154 independent reflections

6962 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.053

S = 1.14

7154 reflections

404 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.38 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008366/xu2732sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008366/xu2732Isup2.hkl

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

[Cd(C8H7O2)2(C6H6N2O)2(H2O)]·H2O	Z = 2
Mr = 662.97	F(000) = 676
Triclinic, P1	Dx = 1.555 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5032 (2) Å	Cell parameters from 8576 reflections
b = 12.3543 (3) Å	θ = 2.4–28.3°
c = 13.6134 (3) Å	µ = 0.83 mm−1
α = 78.278 (3)°	T = 102 K
β = 69.776 (2)°	Block, colorless
γ = 71.746 (3)°	0.40 × 0.20 × 0.15 mm
V = 1416.18 (6) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	7154 independent reflections
Radiation source: fine-focus sealed tube	6962 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 28.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.819, Tmax = 0.881	k = −16→16
25922 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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0175P)2 + 1.1925P] where P = (Fo2 + 2Fc2)/3
7154 reflections	(Δ/σ)max = 0.001
404 parameters	Δρmax = 0.56 e Å−3
0 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	0.141608 (11)	0.121190 (8)	0.094078 (7)	0.00977 (3)
O1	0.21408 (12)	0.17237 (9)	0.21480 (8)	0.0153 (2)
O2	0.43486 (13)	0.06777 (9)	0.11883 (8)	0.0158 (2)
O3	−0.09543 (12)	0.15690 (9)	0.04849 (8)	0.0150 (2)
O4	−0.08901 (13)	0.26914 (10)	0.15327 (9)	0.0164 (2)
O5	0.56683 (13)	0.41643 (10)	−0.38584 (9)	0.0199 (2)
O6	−0.03527 (14)	−0.40999 (9)	0.37641 (9)	0.0178 (2)
O7	0.25490 (14)	−0.02091 (10)	−0.01623 (9)	0.0183 (2)
H71	0.345 (3)	−0.038 (2)	−0.0464 (19)	0.030 (6)*
H72	0.214 (3)	−0.064 (2)	−0.0261 (18)	0.028 (6)*
O8	−0.06722 (16)	0.23407 (12)	0.36356 (10)	0.0224 (2)
H81	−0.115 (3)	0.252 (2)	0.323 (2)	0.039 (7)*
H82	0.021 (3)	0.216 (2)	0.326 (2)	0.039 (7)*
N1	0.24879 (15)	0.23682 (11)	−0.05300 (10)	0.0131 (2)
N2	0.32591 (17)	0.46852 (14)	−0.40532 (11)	0.0222 (3)
H21	0.355 (3)	0.502 (2)	−0.4672 (19)	0.029 (6)*
H22	0.235 (3)	0.4542 (19)	−0.3832 (18)	0.027 (6)*
N3	0.06838 (15)	−0.03017 (11)	0.21984 (10)	0.0139 (2)
N4	0.02873 (16)	−0.36600 (12)	0.50561 (10)	0.0162 (2)
H41	0.056 (2)	−0.3201 (18)	0.5322 (17)	0.022 (5)*
H42	0.020 (2)	−0.4306 (19)	0.5415 (16)	0.019 (5)*
C1	0.35814 (17)	0.12189 (12)	0.19750 (11)	0.0122 (3)
C2	0.43118 (17)	0.12606 (13)	0.27780 (11)	0.0138 (3)
C3	0.34802 (19)	0.19738 (14)	0.35725 (13)	0.0190 (3)
H3	0.2493	0.2439	0.3587	0.023*
C4	0.4114 (2)	0.19972 (16)	0.43464 (13)	0.0223 (3)
H4	0.3544	0.2478	0.4874	0.027*
C5	0.55876 (19)	0.13100 (15)	0.43413 (12)	0.0196 (3)
C6	0.64170 (19)	0.06017 (15)	0.35394 (13)	0.0208 (3)
H6	0.7406	0.0138	0.3523	0.025*
C7	0.57917 (18)	0.05760 (14)	0.27640 (12)	0.0174 (3)
H7	0.6364	0.0099	0.2233	0.021*
C8	0.6266 (2)	0.13244 (18)	0.51874 (14)	0.0276 (4)
H8A	0.7263	0.0775	0.5079	0.041*
H8B	0.5582	0.1132	0.5865	0.041*
H8C	0.6384	0.2075	0.5157	0.041*
C9	−0.16048 (17)	0.24072 (12)	0.10406 (11)	0.0123 (3)
C10	−0.32334 (17)	0.30742 (12)	0.10992 (12)	0.0130 (3)
C11	−0.41385 (18)	0.37317 (13)	0.19319 (12)	0.0166 (3)
H11	−0.3706	0.3785	0.2432	0.020*
C12	−0.56823 (19)	0.43074 (14)	0.20192 (13)	0.0195 (3)
H12	−0.6280	0.4732	0.2584	0.023*
C13	−0.63418 (18)	0.42543 (13)	0.12678 (13)	0.0177 (3)
C14	−0.54103 (18)	0.36423 (13)	0.04114 (13)	0.0176 (3)
H14	−0.5822	0.3633	−0.0114	0.021*
C15	−0.38809 (18)	0.30477 (13)	0.03297 (12)	0.0152 (3)
H15	−0.3283	0.2629	−0.0240	0.018*
C16	−0.80317 (19)	0.48229 (16)	0.13748 (15)	0.0257 (4)
H16A	−0.8456	0.5324	0.1920	0.039*
H16B	−0.8590	0.4248	0.1551	0.039*
H16C	−0.8127	0.5259	0.0721	0.039*
C17	0.16137 (17)	0.33676 (13)	−0.08530 (12)	0.0152 (3)
H17	0.0612	0.3651	−0.0419	0.018*
C18	0.21389 (18)	0.39975 (13)	−0.18067 (12)	0.0166 (3)
H18	0.1500	0.4686	−0.2009	0.020*
C19	0.36446 (17)	0.35759 (13)	−0.24544 (11)	0.0134 (3)
C20	0.45742 (18)	0.25694 (13)	−0.20997 (12)	0.0153 (3)
H20	0.5599	0.2288	−0.2501	0.018*
C21	0.39564 (18)	0.19876 (13)	−0.11404 (12)	0.0148 (3)
H21A	0.4582	0.1308	−0.0911	0.018*
C22	0.42827 (18)	0.41740 (13)	−0.35244 (12)	0.0154 (3)
C23	0.01222 (18)	−0.10290 (13)	0.19260 (12)	0.0153 (3)
H23	−0.0121	−0.0849	0.1296	0.018*
C24	−0.01121 (18)	−0.20371 (13)	0.25425 (12)	0.0158 (3)
H24	−0.0495	−0.2523	0.2325	0.019*
C25	0.02332 (17)	−0.23100 (12)	0.34907 (11)	0.0125 (3)
C26	0.07689 (18)	−0.15443 (13)	0.37961 (12)	0.0160 (3)
H26	0.0976	−0.1688	0.4437	0.019*
C27	0.09879 (18)	−0.05607 (13)	0.31243 (12)	0.0156 (3)
H27	0.1363	−0.0057	0.3326	0.019*
C28	0.00343 (17)	−0.34324 (12)	0.41280 (11)	0.0131 (3)

	U11	U22	U33	U12	U13	U23
Cd1	0.01036 (5)	0.01012 (5)	0.00874 (5)	−0.00363 (4)	−0.00264 (4)	0.00016 (3)
O1	0.0118 (5)	0.0192 (5)	0.0162 (5)	−0.0038 (4)	−0.0054 (4)	−0.0029 (4)
O2	0.0165 (5)	0.0163 (5)	0.0152 (5)	−0.0032 (4)	−0.0054 (4)	−0.0038 (4)
O3	0.0122 (5)	0.0160 (5)	0.0169 (5)	−0.0018 (4)	−0.0048 (4)	−0.0040 (4)
O4	0.0142 (5)	0.0201 (5)	0.0177 (5)	−0.0041 (4)	−0.0076 (4)	−0.0034 (4)
O5	0.0164 (5)	0.0272 (6)	0.0148 (5)	−0.0095 (5)	−0.0039 (4)	0.0046 (4)
O6	0.0239 (6)	0.0157 (5)	0.0185 (5)	−0.0105 (4)	−0.0098 (4)	0.0023 (4)
O7	0.0141 (5)	0.0195 (6)	0.0213 (6)	−0.0072 (5)	0.0013 (4)	−0.0100 (4)
O8	0.0184 (6)	0.0347 (7)	0.0148 (5)	−0.0063 (5)	−0.0039 (5)	−0.0075 (5)
N1	0.0138 (6)	0.0132 (6)	0.0125 (6)	−0.0055 (5)	−0.0033 (5)	0.0003 (4)
N2	0.0179 (7)	0.0322 (8)	0.0158 (6)	−0.0125 (6)	−0.0065 (5)	0.0105 (6)
N3	0.0152 (6)	0.0144 (6)	0.0121 (6)	−0.0049 (5)	−0.0038 (5)	−0.0006 (4)
N4	0.0225 (7)	0.0131 (6)	0.0147 (6)	−0.0078 (5)	−0.0072 (5)	0.0024 (5)
C1	0.0128 (6)	0.0106 (6)	0.0138 (6)	−0.0055 (5)	−0.0045 (5)	0.0017 (5)
C2	0.0135 (6)	0.0162 (7)	0.0128 (6)	−0.0060 (5)	−0.0045 (5)	0.0001 (5)
C3	0.0157 (7)	0.0226 (8)	0.0205 (7)	−0.0035 (6)	−0.0068 (6)	−0.0063 (6)
C4	0.0224 (8)	0.0292 (9)	0.0190 (8)	−0.0074 (7)	−0.0063 (6)	−0.0091 (6)
C5	0.0207 (8)	0.0278 (8)	0.0155 (7)	−0.0132 (7)	−0.0078 (6)	0.0014 (6)
C6	0.0142 (7)	0.0299 (9)	0.0190 (7)	−0.0055 (6)	−0.0079 (6)	0.0006 (6)
C7	0.0146 (7)	0.0223 (8)	0.0145 (7)	−0.0037 (6)	−0.0044 (6)	−0.0022 (6)
C8	0.0299 (9)	0.0432 (11)	0.0195 (8)	−0.0202 (8)	−0.0128 (7)	0.0018 (7)
C9	0.0119 (6)	0.0136 (6)	0.0109 (6)	−0.0049 (5)	−0.0029 (5)	0.0016 (5)
C10	0.0114 (6)	0.0124 (6)	0.0157 (7)	−0.0038 (5)	−0.0049 (5)	−0.0002 (5)
C11	0.0158 (7)	0.0173 (7)	0.0183 (7)	−0.0032 (6)	−0.0067 (6)	−0.0042 (6)
C12	0.0162 (7)	0.0189 (7)	0.0209 (8)	−0.0012 (6)	−0.0037 (6)	−0.0057 (6)
C13	0.0130 (7)	0.0150 (7)	0.0246 (8)	−0.0029 (5)	−0.0067 (6)	−0.0004 (6)
C14	0.0169 (7)	0.0159 (7)	0.0241 (8)	−0.0038 (6)	−0.0119 (6)	−0.0019 (6)
C15	0.0151 (7)	0.0136 (7)	0.0177 (7)	−0.0028 (5)	−0.0064 (6)	−0.0027 (5)
C16	0.0142 (7)	0.0257 (9)	0.0352 (10)	0.0002 (6)	−0.0095 (7)	−0.0039 (7)
C17	0.0117 (6)	0.0170 (7)	0.0145 (7)	−0.0040 (5)	−0.0029 (5)	0.0015 (5)
C18	0.0143 (7)	0.0164 (7)	0.0162 (7)	−0.0037 (6)	−0.0051 (6)	0.0044 (6)
C19	0.0151 (7)	0.0151 (7)	0.0114 (6)	−0.0072 (5)	−0.0047 (5)	0.0018 (5)
C20	0.0143 (7)	0.0154 (7)	0.0136 (7)	−0.0040 (5)	−0.0017 (5)	−0.0008 (5)
C21	0.0154 (7)	0.0129 (7)	0.0144 (7)	−0.0029 (5)	−0.0042 (5)	0.0002 (5)
C22	0.0174 (7)	0.0161 (7)	0.0123 (6)	−0.0073 (6)	−0.0035 (5)	0.0019 (5)
C23	0.0190 (7)	0.0170 (7)	0.0115 (6)	−0.0071 (6)	−0.0059 (5)	0.0009 (5)
C24	0.0216 (7)	0.0152 (7)	0.0132 (7)	−0.0082 (6)	−0.0058 (6)	−0.0012 (5)
C25	0.0124 (6)	0.0117 (6)	0.0123 (6)	−0.0037 (5)	−0.0033 (5)	0.0012 (5)
C26	0.0202 (7)	0.0171 (7)	0.0142 (7)	−0.0088 (6)	−0.0088 (6)	0.0028 (5)
C27	0.0203 (7)	0.0154 (7)	0.0145 (7)	−0.0091 (6)	−0.0073 (6)	0.0014 (5)
C28	0.0111 (6)	0.0128 (6)	0.0136 (6)	−0.0036 (5)	−0.0025 (5)	0.0009 (5)

Cd1—O1	2.2478 (11)	C8—C5	1.507 (2)
Cd1—O3	2.4263 (11)	C8—H8A	0.9600
Cd1—O4	2.3794 (11)	C8—H8B	0.9600
Cd1—O7	2.2947 (11)	C8—H8C	0.9600
Cd1—N1	2.3295 (12)	C9—C10	1.491 (2)
Cd1—N3	2.3671 (13)	C10—C11	1.395 (2)
O1—C1	1.2730 (18)	C10—C15	1.396 (2)
O2—C1	1.2535 (18)	C11—H11	0.9300
O3—C9	1.2730 (18)	C12—C11	1.390 (2)
O4—C9	1.2622 (18)	C12—C13	1.393 (2)
O5—C22	1.2325 (19)	C12—H12	0.9300
O6—C28	1.2422 (18)	C13—C16	1.506 (2)
O7—H71	0.79 (3)	C14—C13	1.393 (2)
O7—H72	0.80 (2)	C14—C15	1.385 (2)
O8—H81	0.79 (3)	C14—H14	0.9300
O8—H82	0.81 (3)	C15—H15	0.9300
N1—C17	1.3406 (19)	C16—H16A	0.9600
N1—C21	1.3435 (19)	C16—H16B	0.9600
N2—C22	1.333 (2)	C16—H16C	0.9600
N2—H21	0.85 (2)	C17—H17	0.9300
N2—H22	0.87 (2)	C18—C17	1.387 (2)
N3—C23	1.3425 (19)	C18—C19	1.394 (2)
N3—C27	1.3433 (19)	C18—H18	0.9300
N4—C28	1.325 (2)	C20—C19	1.387 (2)
N4—H41	0.87 (2)	C20—H20	0.9300
N4—H42	0.86 (2)	C21—C20	1.385 (2)
C1—C2	1.500 (2)	C21—H21A	0.9300
C2—C3	1.390 (2)	C22—C19	1.506 (2)
C2—C7	1.392 (2)	C23—C24	1.387 (2)
C3—C4	1.391 (2)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.391 (2)	C25—C24	1.391 (2)
C4—H4	0.9300	C26—C25	1.391 (2)
C6—C5	1.393 (2)	C26—C27	1.390 (2)
C6—C7	1.388 (2)	C26—H26	0.9300
C6—H6	0.9300	C27—H27	0.9300
C7—H7	0.9300	C28—C25	1.5077 (19)
O1—Cd1—O3	137.23 (4)	O4—C9—O3	121.19 (13)
O1—Cd1—O4	83.65 (4)	O4—C9—C10	119.45 (13)
O1—Cd1—O7	133.14 (4)	C11—C10—C15	118.94 (14)
O1—Cd1—N1	99.39 (4)	C11—C10—C9	120.24 (13)
O1—Cd1—N3	87.65 (4)	C15—C10—C9	120.82 (13)
O4—Cd1—O3	54.71 (4)	C10—C11—H11	119.8
O7—Cd1—O3	88.51 (4)	C12—C11—C10	120.44 (14)
O7—Cd1—O4	143.07 (4)	C12—C11—H11	119.8
O7—Cd1—N1	84.40 (4)	C11—C12—C13	120.59 (15)
O7—Cd1—N3	82.88 (4)	C11—C12—H12	119.7
N1—Cd1—O3	93.12 (4)	C13—C12—H12	119.7
N1—Cd1—O4	93.53 (4)	C12—C13—C14	118.64 (14)
N1—Cd1—N3	167.06 (4)	C12—C13—C16	121.48 (15)
N3—Cd1—O3	88.91 (4)	C14—C13—C16	119.87 (15)
N3—Cd1—O4	98.06 (4)	C13—C14—H14	119.5
C1—O1—Cd1	105.84 (9)	C15—C14—C13	121.06 (14)
C9—O3—Cd1	90.83 (8)	C15—C14—H14	119.5
C9—O4—Cd1	93.27 (9)	C10—C15—H15	119.9
Cd1—O7—H71	123.1 (17)	C14—C15—C10	120.21 (14)
Cd1—O7—H72	127.0 (17)	C14—C15—H15	119.9
H72—O7—H71	110 (2)	C13—C16—H16A	109.5
H81—O8—H82	103 (3)	C13—C16—H16B	109.5
C17—N1—Cd1	121.04 (10)	C13—C16—H16C	109.5
C17—N1—C21	118.25 (13)	H16A—C16—H16B	109.5
C21—N1—Cd1	120.31 (10)	H16A—C16—H16C	109.5
C22—N2—H21	120.3 (15)	H16B—C16—H16C	109.5
C22—N2—H22	119.5 (15)	N1—C17—C18	122.87 (14)
H22—N2—H21	119 (2)	N1—C17—H17	118.6
C23—N3—Cd1	118.71 (10)	C18—C17—H17	118.6
C23—N3—C27	117.68 (13)	C17—C18—C19	118.55 (14)
C27—N3—Cd1	123.03 (10)	C17—C18—H18	120.7
C28—N4—H41	124.1 (14)	C19—C18—H18	120.7
C28—N4—H42	118.4 (14)	C18—C19—C22	122.10 (14)
H42—N4—H41	117.4 (19)	C20—C19—C18	118.62 (13)
O1—C1—C2	117.01 (13)	C20—C19—C22	119.28 (13)
O2—C1—O1	121.75 (13)	C19—C20—H20	120.4
O2—C1—C2	121.20 (13)	C21—C20—C19	119.15 (14)
C3—C2—C1	119.49 (14)	C21—C20—H20	120.4
C3—C2—C7	119.02 (14)	N1—C21—C20	122.46 (14)
C7—C2—C1	121.47 (13)	N1—C21—H21A	118.8
C2—C3—C4	120.48 (15)	C20—C21—H21A	118.8
C2—C3—H3	119.8	O5—C22—N2	124.40 (14)
C4—C3—H3	119.8	O5—C22—C19	120.11 (14)
C3—C4—H4	119.6	N2—C22—C19	115.49 (13)
C5—C4—C3	120.82 (15)	N3—C23—C24	122.90 (14)
C5—C4—H4	119.6	N3—C23—H23	118.5
C4—C5—C6	118.36 (14)	C24—C23—H23	118.5
C4—C5—C8	120.82 (16)	C23—C24—C25	119.07 (14)
C6—C5—C8	120.82 (16)	C23—C24—H24	120.5
C5—C6—H6	119.5	C25—C24—H24	120.5
C7—C6—C5	121.08 (15)	C24—C25—C26	118.47 (13)
C7—C6—H6	119.5	C24—C25—C28	118.30 (13)
C2—C7—H7	119.9	C26—C25—C28	123.23 (13)
C6—C7—C2	120.24 (15)	C25—C26—H26	120.7
C6—C7—H7	119.9	C27—C26—C25	118.64 (14)
C5—C8—H8A	109.5	C27—C26—H26	120.7
C5—C8—H8B	109.5	N3—C27—C26	123.20 (14)
C5—C8—H8C	109.5	N3—C27—H27	118.4
H8A—C8—H8B	109.5	C26—C27—H27	118.4
H8A—C8—H8C	109.5	O6—C28—N4	123.03 (14)
H8B—C8—H8C	109.5	O6—C28—C25	119.00 (13)
O3—C9—C10	119.35 (13)	N4—C28—C25	117.97 (13)
O3—Cd1—O1—C1	178.82 (8)	O1—C1—C2—C3	−9.6 (2)
O4—Cd1—O1—C1	−168.65 (9)	O1—C1—C2—C7	168.54 (14)
O7—Cd1—O1—C1	15.00 (11)	O2—C1—C2—C3	172.66 (14)
N1—Cd1—O1—C1	−76.11 (9)	O2—C1—C2—C7	−9.2 (2)
N3—Cd1—O1—C1	92.97 (9)	C1—C2—C3—C4	177.80 (14)
O1—Cd1—O3—C9	15.18 (11)	C7—C2—C3—C4	−0.4 (2)
O4—Cd1—O3—C9	−0.14 (8)	C1—C2—C7—C6	−177.67 (14)
O7—Cd1—O3—C9	−176.56 (9)	C3—C2—C7—C6	0.5 (2)
N1—Cd1—O3—C9	−92.25 (9)	C2—C3—C4—C5	0.0 (3)
N3—Cd1—O3—C9	100.53 (9)	C3—C4—C5—C6	0.3 (3)
O1—Cd1—O4—C9	−169.47 (9)	C3—C4—C5—C8	−179.23 (16)
O3—Cd1—O4—C9	0.14 (8)	C5—C6—C7—C2	−0.2 (2)
O7—Cd1—O4—C9	6.09 (12)	C7—C6—C5—C4	−0.2 (2)
N1—Cd1—O4—C9	91.47 (9)	C7—C6—C5—C8	179.32 (15)
N3—Cd1—O4—C9	−82.76 (9)	O3—C9—C10—C11	159.36 (14)
O1—Cd1—N1—C17	−98.58 (11)	O3—C9—C10—C15	−20.3 (2)
O1—Cd1—N1—C21	88.82 (11)	O4—C9—C10—C11	−21.4 (2)
O3—Cd1—N1—C17	40.37 (11)	O4—C9—C10—C15	158.92 (14)
O3—Cd1—N1—C21	−132.23 (11)	C9—C10—C11—C12	−176.66 (14)
O4—Cd1—N1—C17	−14.44 (11)	C15—C10—C11—C12	3.0 (2)
O4—Cd1—N1—C21	172.96 (11)	C9—C10—C15—C14	177.96 (14)
O7—Cd1—N1—C17	128.57 (12)	C11—C10—C15—C14	−1.7 (2)
O7—Cd1—N1—C21	−44.04 (11)	C13—C12—C11—C10	−1.2 (2)
N3—Cd1—N1—C17	139.16 (18)	C11—C12—C13—C14	−1.9 (2)
N3—Cd1—N1—C21	−33.4 (3)	C11—C12—C13—C16	176.95 (15)
O1—Cd1—N3—C23	−178.51 (11)	C15—C14—C13—C12	3.3 (2)
O1—Cd1—N3—C27	−7.44 (12)	C15—C14—C13—C16	−175.65 (15)
O3—Cd1—N3—C23	44.13 (11)	C13—C14—C15—C10	−1.5 (2)
O3—Cd1—N3—C27	−144.80 (12)	C19—C18—C17—N1	−0.4 (2)
O4—Cd1—N3—C23	98.24 (11)	C17—C18—C19—C20	−2.6 (2)
O4—Cd1—N3—C27	−90.69 (12)	C17—C18—C19—C22	177.02 (14)
O7—Cd1—N3—C23	−44.50 (11)	C21—C20—C19—C18	3.1 (2)
O7—Cd1—N3—C27	126.57 (12)	C21—C20—C19—C22	−176.49 (13)
N1—Cd1—N3—C23	−55.1 (2)	N1—C21—C20—C19	−0.8 (2)
N1—Cd1—N3—C27	115.9 (2)	O5—C22—C19—C18	145.44 (16)
Cd1—N1—C17—C18	−170.02 (12)	O5—C22—C19—C20	−35.0 (2)
C21—N1—C17—C18	2.7 (2)	N2—C22—C19—C18	−34.9 (2)
Cd1—N1—C21—C20	170.65 (11)	N2—C22—C19—C20	144.70 (15)
C17—N1—C21—C20	−2.2 (2)	N3—C23—C24—C25	0.6 (2)
Cd1—N3—C23—C24	169.79 (12)	C26—C25—C24—C23	1.5 (2)
C27—N3—C23—C24	−1.8 (2)	C28—C25—C24—C23	−177.50 (14)
Cd1—N3—C27—C26	−170.25 (12)	C27—C26—C25—C24	−2.2 (2)
C23—N3—C27—C26	0.9 (2)	C27—C26—C25—C28	176.66 (14)
Cd1—O1—C1—O2	7.16 (16)	C25—C26—C27—N3	1.1 (2)
Cd1—O1—C1—C2	−170.52 (10)	O6—C28—C25—C24	3.6 (2)
Cd1—O3—C9—O4	0.24 (14)	O6—C28—C25—C26	−175.30 (14)
Cd1—O3—C9—C10	179.43 (11)	N4—C28—C25—C24	−176.55 (14)
Cd1—O4—C9—O3	−0.25 (14)	N4—C28—C25—C26	4.5 (2)
Cd1—O4—C9—C10	−179.43 (11)

Cg3 and Cg4 are the centroids of the N1/C17-C21 and N3/C23-C27 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O5i	0.85 (2)	2.05 (2)	2.8990 (19)	177 (2)
N2—H22···O6ii	0.87 (3)	2.10 (3)	2.948 (2)	163 (2)
N4—H41···O8iii	0.87 (2)	1.99 (2)	2.822 (2)	160 (2)
N4—H42···O6iv	0.86 (2)	2.05 (2)	2.8979 (18)	171 (2)
O7—H71···O2v	0.79 (3)	1.93 (3)	2.7186 (19)	175 (2)
O7—H72···O3ii	0.80 (3)	1.97 (3)	2.7690 (18)	174 (3)
O8—H81···O4	0.79 (3)	2.21 (3)	2.8767 (18)	143 (3)
O8—H82···O1	0.80 (3)	1.93 (3)	2.7269 (18)	169 (3)
C6—H6···Cg4vi	0.93	2.82	3.7196 (20)	163
C14—H14···Cg3vii	0.93	2.78	3.6840 (19)	164

Table 1

Selected bond lengths (Å)

Cd1—O1	2.2478 (11)
Cd1—O3	2.4263 (11)
Cd1—O4	2.3794 (11)
Cd1—O7	2.2947 (11)
Cd1—N1	2.3295 (12)
Cd1—N3	2.3671 (13)

Table 2

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the N1/C17-C21 and N3/C23-C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O5i	0.85 (2)	2.05 (2)	2.8990 (19)	177 (2)
N2—H22⋯O6ii	0.87 (3)	2.10 (3)	2.948 (2)	163 (2)
N4—H41⋯O8iii	0.87 (2)	1.99 (2)	2.822 (2)	160 (2)
N4—H42⋯O6iv	0.86 (2)	2.05 (2)	2.8979 (18)	171 (2)
O7—H71⋯O2v	0.79 (3)	1.93 (3)	2.7186 (19)	175 (2)
O7—H72⋯O3ii	0.80 (3)	1.97 (3)	2.7690 (18)	174 (3)
O8—H81⋯O4	0.79 (3)	2.21 (3)	2.8767 (18)	143 (3)
O8—H82⋯O1	0.80 (3)	1.93 (3)	2.7269 (18)	169 (3)
C6—H6⋯Cg4vi	0.93	2.82	3.720 (2)	163
C14—H14⋯Cg3vii	0.93	2.78	3.6840 (19)	164

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