Diaqua-bis-(5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ato-κN,O)cadmium(II) 3.5-hydrate.

In the title complex, [Cd(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·3.5H(2)O, the Cd(II) is coordinated by two water mol-ecules and N,O-chelated by two 5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ate anions in a distorted octa-hedral geometry. The two imidazole rings are oriented to each other with a dihedral angle of 75.1 (2)°. Strong O-H⋯O hydrogen bonds between protonated and deprotonated carboxyl-ate groups occur in the mol-ecular structure. In the crystal structure extensive O-H⋯O and N-H⋯O hydrogen bonds help to stabilize the three-dimensional supra-molecular framework. The propyl groups of anions are disordered over two sites with refined occupancies of 0.768 (6):0.232 (6) and 0.642 (8):0.358 (8).

Related literature

For the potential uses and diverse structural types of metal complexes with the imidazole-4,5-dicarboxyl­ate ligand, see: Zou et al. (2006 ▶); Li et al. (2006 ▶); Liu et al. (2004 ▶); Sun et al. (2005 ▶). For related structures, see: Yan et al. (2010 ▶); Li et al. (2010 ▶); Song et al. (2010 ▶); He et al. (2010 ▶); Fan et al. (2010 ▶).

Experimental

Crystal data

[Cd(C8H9N2O4)2(H2O)2]·3.5H2O

M = 605.83

Triclinic,

a = 10.6228 (12) Å

b = 10.7000 (12) Å

c = 11.3694 (13) Å

α = 83.690 (1)°

β = 81.701 (1)°

γ = 87.441 (1)°

V = 1270.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.93 mm−1

T = 296 K

0.29 × 0.24 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.775, T max = 0.829

6589 measured reflections

4494 independent reflections

3730 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.05

4494 reflections

346 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536810031466/xu5001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031466/xu5001Isup2.hkl

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

[Cd(C8H9N2O4)2(H2O)2]·3.5H2O	Z = 2
Mr = 605.83	F(000) = 618
Triclinic, P1	Dx = 1.584 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6228 (12) Å	Cell parameters from 3600 reflections
b = 10.7000 (12) Å	θ = 1.4–25.0°
c = 11.3694 (13) Å	µ = 0.93 mm−1
α = 83.690 (1)°	T = 296 K
β = 81.701 (1)°	Block, colorless
γ = 87.441 (1)°	0.29 × 0.24 × 0.21 mm
V = 1270.5 (2) Å3

Bruker APEXII area-detector diffractometer	4494 independent reflections
Radiation source: fine-focus sealed tube	3730 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scan	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.775, Tmax = 0.829	k = −12→8
6589 measured reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1685P] where P = (Fo2 + 2Fc2)/3
4494 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.46 e Å−3
7 restraints	Δρmin = −0.59 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	Occ. (<1)
Cd1	0.84023 (3)	0.29169 (3)	0.19976 (2)	0.04816 (13)
O1	0.8778 (4)	−0.1913 (3)	0.5186 (3)	0.0698 (9)
O2	0.8413 (3)	−0.1136 (3)	0.6913 (3)	0.0701 (9)
O3	0.8810 (3)	0.0754 (3)	0.1940 (2)	0.0565 (7)
O4	0.8944 (3)	−0.1083 (3)	0.3037 (3)	0.0656 (8)
O5	0.7595 (3)	0.5000 (3)	0.2111 (3)	0.0553 (7)
O6	0.5964 (3)	0.6304 (3)	0.1835 (3)	0.0660 (8)
O7	0.3809 (3)	0.6208 (3)	0.1350 (3)	0.0604 (8)
O8	0.2516 (3)	0.4784 (3)	0.0948 (3)	0.0606 (8)
N1	0.8262 (3)	0.2015 (3)	0.3933 (3)	0.0454 (7)
N2	0.8116 (3)	0.1310 (3)	0.5823 (3)	0.0550 (9)
H2	0.8009	0.1302	0.6588	0.066*
N3	0.6294 (3)	0.2956 (3)	0.1734 (3)	0.0438 (7)
N4	0.4358 (3)	0.2862 (3)	0.1287 (3)	0.0479 (8)
H4	0.3681	0.2556	0.1112	0.058*
C1	0.8362 (3)	0.0280 (4)	0.5209 (3)	0.0447 (9)
C2	0.8454 (3)	0.0742 (3)	0.4021 (3)	0.0395 (8)
C3	0.8069 (5)	0.2337 (4)	0.5040 (4)	0.0591 (11)
C4	0.8760 (4)	0.0090 (4)	0.2913 (3)	0.0473 (9)
C5	0.8512 (4)	−0.0992 (4)	0.5834 (4)	0.0517 (10)
C6A	0.7979 (9)	0.3683 (10)	0.5325 (10)	0.085 (3)	0.772 (6)
H6A	0.8215	0.3717	0.6114	0.102*	0.772 (6)
H6B	0.8579	0.4174	0.4753	0.102*	0.772 (6)
C7A	0.6674 (9)	0.4249 (7)	0.5292 (8)	0.107 (3)	0.772 (6)
H7A	0.6091	0.3854	0.5949	0.128*	0.772 (6)
H7B	0.6379	0.4108	0.4550	0.128*	0.772 (6)
C8A	0.6699 (11)	0.5651 (7)	0.5390 (9)	0.129 (4)	0.772 (6)
H8A	0.5848	0.5970	0.5604	0.193*	0.772 (6)
H8B	0.7059	0.6073	0.4635	0.193*	0.772 (6)
H8C	0.7207	0.5796	0.5992	0.193*	0.772 (6)
C6B	0.740 (4)	0.350 (4)	0.549 (4)	0.085 (3)	0.228 (6)
H6C	0.6751	0.3816	0.5002	0.102*	0.228 (6)
H6D	0.6998	0.3328	0.6313	0.102*	0.228 (6)
C7B	0.844 (3)	0.442 (3)	0.540 (3)	0.107 (3)	0.228 (6)
H7C	0.8078	0.5259	0.5500	0.128*	0.228 (6)
H7D	0.8951	0.4445	0.4616	0.128*	0.228 (6)
C8B	0.924 (3)	0.399 (3)	0.637 (3)	0.129 (4)	0.228 (6)
H8D	0.9722	0.4679	0.6515	0.193*	0.228 (6)
H8E	0.9808	0.3317	0.6117	0.193*	0.228 (6)
H8F	0.8695	0.3699	0.7086	0.193*	0.228 (6)
C9	0.5736 (3)	0.4138 (3)	0.1688 (3)	0.0397 (8)
C10	0.4529 (3)	0.4099 (4)	0.1405 (3)	0.0413 (8)
C11	0.5431 (4)	0.2209 (4)	0.1490 (4)	0.0509 (10)
C12	0.6485 (4)	0.5201 (4)	0.1898 (3)	0.0470 (9)
C13	0.3529 (4)	0.5090 (4)	0.1221 (3)	0.0481 (9)
C14A	0.5509 (17)	0.0797 (5)	0.1655 (9)	0.061 (3)	0.642 (8)
H14A	0.6361	0.0508	0.1353	0.073*	0.642 (8)
H14B	0.4918	0.0464	0.1201	0.073*	0.642 (8)
C15A	0.5189 (11)	0.0302 (8)	0.2979 (9)	0.081 (3)	0.642 (8)
H15A	0.5740	0.0680	0.3443	0.098*	0.642 (8)
H15B	0.4315	0.0537	0.3267	0.098*	0.642 (8)
C16A	0.5361 (10)	−0.1097 (8)	0.3138 (11)	0.108 (4)	0.642 (8)
H16A	0.5605	−0.1354	0.3912	0.161*	0.642 (8)
H16B	0.6013	−0.1358	0.2531	0.161*	0.642 (8)
H16C	0.4576	−0.1479	0.3075	0.161*	0.642 (8)
C14B	0.572 (3)	0.0878 (9)	0.119 (2)	0.061 (3)	0.358 (8)
H14C	0.6611	0.0664	0.1216	0.073*	0.358 (8)
H14D	0.5526	0.0790	0.0400	0.073*	0.358 (8)
C15B	0.4893 (14)	0.0002 (15)	0.2123 (14)	0.081 (3)	0.358 (8)
H15C	0.4005	0.0244	0.2101	0.098*	0.358 (8)
H15D	0.5017	−0.0851	0.1905	0.098*	0.358 (8)
C16B	0.518 (3)	0.002 (2)	0.3363 (17)	0.108 (4)	0.358 (8)
H16D	0.4796	−0.0688	0.3859	0.161*	0.358 (8)
H16E	0.4832	0.0784	0.3669	0.161*	0.358 (8)
H16F	0.6080	−0.0025	0.3363	0.161*	0.358 (8)
O1W	0.8927 (3)	0.3292 (4)	0.0015 (3)	0.0955 (13)
H1W	0.9095	0.2617	−0.0314	0.143*
H2W	0.8569	0.3905	−0.0363	0.143*
O2W	1.0419 (3)	0.3400 (4)	0.2218 (3)	0.0897 (12)
H3W	1.0847	0.4010	0.1869	0.135*
H4W	1.0911	0.2778	0.2405	0.135*
O3W	0.9149 (6)	0.0145 (6)	0.9607 (5)	0.0625 (15)	0.50
H5W	0.9951	0.0020	0.9528	0.094*	0.50
H6W	0.9090	0.0145	1.0360	0.094*	0.50
O4W	0.7737 (5)	0.1534 (4)	0.8233 (3)	0.1211 (17)
H7W	0.8269	0.1083	0.8598	0.182*
H8W	0.7288	0.2197	0.8353	0.182*
O5W	0.1097 (3)	0.2735 (3)	0.8678 (3)	0.0718 (9)
H9W	0.1608	0.3312	0.8299	0.108*
H10W	0.1151	0.2123	0.8255	0.108*
O6W	0.2598 (4)	0.1582 (4)	0.0406 (4)	0.1044 (13)
H11W	0.2130	0.0949	0.0534	0.157*
H12W	0.2045	0.2161	0.0283	0.157*
H1	0.876 (8)	−0.162 (7)	0.449 (2)	0.157*
H7	0.453 (3)	0.632 (7)	0.149 (7)	0.157*

	U11	U22	U33	U12	U13	U23
Cd1	0.04170 (18)	0.0518 (2)	0.0479 (2)	0.00347 (13)	−0.00891 (12)	0.01025 (13)
O1	0.091 (2)	0.0495 (19)	0.067 (2)	−0.0007 (16)	−0.0173 (19)	0.0084 (16)
O2	0.070 (2)	0.079 (2)	0.0510 (19)	0.0116 (17)	−0.0047 (15)	0.0254 (15)
O3	0.0718 (19)	0.0587 (18)	0.0362 (15)	0.0191 (14)	−0.0077 (13)	−0.0008 (13)
O4	0.096 (2)	0.0453 (18)	0.0579 (18)	0.0127 (16)	−0.0199 (16)	−0.0092 (14)
O5	0.0471 (16)	0.0495 (17)	0.0723 (19)	−0.0052 (13)	−0.0187 (14)	−0.0049 (14)
O6	0.0647 (19)	0.0398 (17)	0.096 (2)	0.0045 (14)	−0.0164 (17)	−0.0127 (16)
O7	0.0518 (17)	0.0510 (18)	0.077 (2)	0.0153 (14)	−0.0098 (15)	−0.0072 (15)
O8	0.0370 (15)	0.069 (2)	0.071 (2)	0.0022 (13)	−0.0108 (13)	0.0172 (15)
N1	0.0490 (18)	0.0434 (19)	0.0429 (18)	0.0051 (14)	−0.0080 (14)	−0.0005 (14)
N2	0.063 (2)	0.064 (2)	0.0355 (17)	0.0098 (17)	−0.0058 (15)	−0.0041 (16)
N3	0.0387 (17)	0.0403 (18)	0.0517 (19)	0.0014 (14)	−0.0099 (14)	0.0012 (14)
N4	0.0384 (17)	0.050 (2)	0.055 (2)	−0.0057 (14)	−0.0133 (14)	0.0032 (15)
C1	0.038 (2)	0.049 (2)	0.044 (2)	0.0000 (16)	−0.0035 (16)	0.0043 (18)
C2	0.0334 (18)	0.044 (2)	0.041 (2)	0.0010 (15)	−0.0074 (15)	−0.0007 (16)
C3	0.076 (3)	0.053 (3)	0.050 (3)	0.009 (2)	−0.014 (2)	−0.006 (2)
C4	0.047 (2)	0.050 (2)	0.045 (2)	0.0074 (17)	−0.0120 (17)	−0.0020 (18)
C5	0.043 (2)	0.061 (3)	0.047 (2)	0.0004 (18)	−0.0083 (18)	0.014 (2)
C6A	0.109 (9)	0.068 (5)	0.078 (5)	0.011 (6)	−0.009 (6)	−0.021 (4)
C7A	0.133 (8)	0.069 (5)	0.115 (7)	0.011 (5)	−0.004 (5)	−0.017 (5)
C8A	0.174 (10)	0.067 (5)	0.136 (8)	0.020 (5)	0.006 (7)	−0.012 (5)
C6B	0.109 (9)	0.068 (5)	0.078 (5)	0.011 (6)	−0.009 (6)	−0.021 (4)
C7B	0.133 (8)	0.069 (5)	0.115 (7)	0.011 (5)	−0.004 (5)	−0.017 (5)
C8B	0.174 (10)	0.067 (5)	0.136 (8)	0.020 (5)	0.006 (7)	−0.012 (5)
C9	0.0391 (19)	0.039 (2)	0.0383 (19)	0.0003 (15)	−0.0029 (15)	0.0024 (15)
C10	0.039 (2)	0.044 (2)	0.0378 (19)	−0.0004 (16)	0.0002 (15)	0.0032 (16)
C11	0.048 (2)	0.043 (2)	0.061 (3)	−0.0025 (18)	−0.0127 (19)	0.0029 (19)
C12	0.048 (2)	0.046 (2)	0.047 (2)	0.0007 (18)	−0.0077 (17)	−0.0012 (17)
C13	0.041 (2)	0.056 (3)	0.040 (2)	0.0088 (18)	0.0033 (16)	0.0075 (18)
C14A	0.061 (7)	0.036 (3)	0.087 (9)	−0.006 (3)	−0.022 (7)	0.007 (4)
C15A	0.062 (5)	0.058 (5)	0.121 (8)	−0.003 (4)	−0.028 (5)	0.023 (5)
C16A	0.101 (7)	0.059 (5)	0.157 (10)	−0.007 (5)	−0.023 (6)	0.023 (6)
C14B	0.061 (7)	0.036 (3)	0.087 (9)	−0.006 (3)	−0.022 (7)	0.007 (4)
C15B	0.062 (5)	0.058 (5)	0.121 (8)	−0.003 (4)	−0.028 (5)	0.023 (5)
C16B	0.101 (7)	0.059 (5)	0.157 (10)	−0.007 (5)	−0.023 (6)	0.023 (6)
O1W	0.085 (3)	0.121 (3)	0.059 (2)	0.052 (2)	0.0107 (18)	0.035 (2)
O2W	0.0499 (19)	0.100 (3)	0.110 (3)	−0.0224 (18)	−0.0251 (18)	0.057 (2)
O3W	0.065 (4)	0.075 (4)	0.048 (3)	0.008 (3)	−0.007 (3)	−0.013 (3)
O4W	0.156 (4)	0.142 (4)	0.072 (2)	0.058 (3)	−0.030 (3)	−0.048 (3)
O5W	0.0623 (19)	0.069 (2)	0.084 (2)	−0.0175 (16)	0.0083 (16)	−0.0255 (17)
O6W	0.101 (3)	0.098 (3)	0.131 (4)	−0.001 (2)	−0.064 (3)	−0.025 (3)

Cd1—O1W	2.238 (3)	C6B—H6D	0.9700
Cd1—O2W	2.281 (3)	C7B—C8B	1.512 (14)
Cd1—N1	2.290 (3)	C7B—H7C	0.9700
Cd1—N3	2.300 (3)	C7B—H7D	0.9700
Cd1—O3	2.341 (3)	C8B—H8D	0.9600
Cd1—O5	2.362 (3)	C8B—H8E	0.9600
O1—C5	1.291 (5)	C8B—H8F	0.9600
O1—H1	0.82 (3)	C9—C10	1.370 (5)
O2—C5	1.209 (5)	C9—C12	1.476 (5)
O3—C4	1.243 (5)	C10—C13	1.487 (5)
O4—C4	1.257 (5)	C11—C14A	1.502 (7)
O5—C12	1.243 (5)	C11—C14B	1.507 (9)
O6—C12	1.280 (5)	C14A—C15A	1.534 (12)
O7—C13	1.275 (5)	C14A—H14A	0.9700
O7—H7	0.82 (4)	C14A—H14B	0.9700
O8—C13	1.229 (5)	C15A—C16A	1.495 (10)
N1—C3	1.327 (5)	C15A—H15A	0.9700
N1—C2	1.363 (5)	C15A—H15B	0.9700
N2—C3	1.341 (5)	C16A—H16A	0.9600
N2—C1	1.364 (5)	C16A—H16B	0.9600
N2—H2	0.8600	C16A—H16C	0.9600
N3—C11	1.320 (5)	C14B—C15B	1.532 (14)
N3—C9	1.371 (5)	C14B—H14C	0.9700
N4—C11	1.346 (5)	C14B—H14D	0.9700
N4—C10	1.368 (5)	C15B—C16B	1.486 (13)
N4—H4	0.8600	C15B—H15C	0.9700
C1—C2	1.377 (5)	C15B—H15D	0.9700
C1—C5	1.478 (6)	C16B—H16D	0.9600
C2—C4	1.495 (5)	C16B—H16E	0.9600
C3—C6A	1.506 (11)	C16B—H16F	0.9600
C3—C6B	1.51 (4)	O1W—H1W	0.8499
C6A—C7A	1.492 (12)	O1W—H2W	0.8500
C6A—H6A	0.9700	O2W—H3W	0.8405
C6A—H6B	0.9700	O2W—H4W	0.8547
C7A—C8A	1.518 (10)	O3W—H5W	0.8500
C7A—H7A	0.9700	O3W—H6W	0.8501
C7A—H7B	0.9700	O4W—H7W	0.8503
C8A—H8A	0.9600	O4W—H8W	0.8498
C8A—H8B	0.9600	O5W—H9W	0.8741
C8A—H8C	0.9600	O5W—H10W	0.8500
C6B—C7B	1.498 (15)	O6W—H11W	0.8452
C6B—H6C	0.9700	O6W—H12W	0.8490
O1W—Cd1—O2W	88.94 (14)	C8B—C7B—H7C	110.3
O1W—Cd1—N1	162.70 (12)	C6B—C7B—H7D	110.3
O2W—Cd1—N1	85.50 (12)	C8B—C7B—H7D	110.3
O1W—Cd1—N3	89.03 (13)	H7C—C7B—H7D	108.5
O2W—Cd1—N3	165.95 (12)	C7B—C8B—H8D	109.5
N1—Cd1—N3	100.21 (11)	C7B—C8B—H8E	109.5
O1W—Cd1—O3	91.83 (12)	H8D—C8B—H8E	109.5
O2W—Cd1—O3	96.11 (12)	C7B—C8B—H8F	109.5
N1—Cd1—O3	72.55 (10)	H8D—C8B—H8F	109.5
N3—Cd1—O3	97.85 (10)	H8E—C8B—H8F	109.5
O1W—Cd1—O5	90.99 (12)	C10—C9—N3	110.1 (3)
O2W—Cd1—O5	94.05 (12)	C10—C9—C12	131.2 (3)
N1—Cd1—O5	105.72 (10)	N3—C9—C12	118.6 (3)
N3—Cd1—O5	72.08 (10)	N4—C10—C9	105.1 (3)
O3—Cd1—O5	169.50 (10)	N4—C10—C13	122.2 (3)
C5—O1—H1	107 (6)	C9—C10—C13	132.6 (4)
C4—O3—Cd1	117.3 (2)	N3—C11—N4	111.0 (3)
C12—O5—Cd1	115.9 (2)	N3—C11—C14A	125.1 (8)
C13—O7—H7	118 (6)	N4—C11—C14A	122.8 (8)
C3—N1—C2	106.7 (3)	N3—C11—C14B	123.8 (15)
C3—N1—Cd1	140.1 (3)	N4—C11—C14B	123.8 (16)
C2—N1—Cd1	113.2 (2)	O5—C12—O6	122.5 (4)
C3—N2—C1	108.9 (3)	O5—C12—C9	119.3 (3)
C3—N2—H2	125.6	O6—C12—C9	118.2 (4)
C1—N2—H2	125.6	O8—C13—O7	125.1 (4)
C11—N3—C9	105.6 (3)	O8—C13—C10	118.7 (4)
C11—N3—Cd1	140.3 (3)	O7—C13—C10	116.2 (4)
C9—N3—Cd1	113.7 (2)	C11—C14A—C15A	110.9 (6)
C11—N4—C10	108.1 (3)	C11—C14A—H14A	109.5
C11—N4—H4	125.9	C15A—C14A—H14A	109.5
C10—N4—H4	125.9	C11—C14A—H14B	109.5
N2—C1—C2	105.1 (3)	C15A—C14A—H14B	109.5
N2—C1—C5	121.4 (4)	H14A—C14A—H14B	108.0
C2—C1—C5	133.4 (4)	C16A—C15A—C14A	110.3 (8)
N1—C2—C1	109.3 (3)	C16A—C15A—H15A	109.6
N1—C2—C4	119.8 (3)	C14A—C15A—H15A	109.6
C1—C2—C4	130.8 (4)	C16A—C15A—H15B	109.6
N1—C3—N2	110.0 (4)	C14A—C15A—H15B	109.6
N1—C3—C6A	123.2 (6)	H15A—C15A—H15B	108.1
N2—C3—C6A	126.4 (6)	C11—C14B—C15B	108.1 (13)
N1—C3—C6B	129 (2)	C11—C14B—H14C	110.1
N2—C3—C6B	117.6 (18)	C15B—C14B—H14C	110.1
O3—C4—O4	125.2 (4)	C11—C14B—H14D	110.1
O3—C4—C2	117.2 (4)	C15B—C14B—H14D	110.1
O4—C4—C2	117.6 (3)	H14C—C14B—H14D	108.4
O2—C5—O1	122.4 (4)	C16B—C15B—C14B	113.8 (19)
O2—C5—C1	119.9 (4)	C16B—C15B—H15C	108.8
O1—C5—C1	117.6 (4)	C14B—C15B—H15C	108.8
C7A—C6A—C3	112.3 (8)	C16B—C15B—H15D	108.8
C7A—C6A—H6A	109.2	C14B—C15B—H15D	108.8
C3—C6A—H6A	109.2	H15C—C15B—H15D	107.7
C7A—C6A—H6B	109.2	C15B—C16B—H16D	109.5
C3—C6A—H6B	109.2	C15B—C16B—H16E	109.5
H6A—C6A—H6B	107.9	H16D—C16B—H16E	109.5
C6A—C7A—C8A	109.4 (8)	C15B—C16B—H16F	109.5
C6A—C7A—H7A	109.8	H16D—C16B—H16F	109.5
C8A—C7A—H7A	109.8	H16E—C16B—H16F	109.5
C6A—C7A—H7B	109.8	Cd1—O1W—H1W	112.0
C8A—C7A—H7B	109.8	Cd1—O1W—H2W	119.5
H7A—C7A—H7B	108.2	H1W—O1W—H2W	118.7
C7B—C6B—C3	104 (3)	Cd1—O2W—H3W	127.7
C7B—C6B—H6C	111.0	Cd1—O2W—H4W	116.0
C3—C6B—H6C	111.0	H3W—O2W—H4W	110.5
C7B—C6B—H6D	111.0	H5W—O3W—H6W	92.8
C3—C6B—H6D	111.0	H7W—O4W—H8W	136.0
H6C—C6B—H6D	109.0	H9W—O5W—H10W	107.5
C6B—C7B—C8B	107 (3)	H11W—O6W—H12W	100.2
C6B—C7B—H7C	110.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4W	0.86	1.89	2.747 (5)	172
N4—H4···O6W	0.86	1.90	2.729 (5)	161
O1—H1···O4	0.82 (3)	1.67 (3)	2.490 (5)	172 (7)
O7—H7···O6	0.82 (4)	1.63 (4)	2.440 (5)	171 (8)
O1W—H1W···O5Wi	0.85	2.27	2.654 (5)	108
O1W—H2W···O8ii	0.85	1.90	2.737 (5)	168
O2W—H3W···O8iii	0.84	2.08	2.852 (5)	152
O2W—H4W···O2iv	0.86	1.99	2.818 (5)	163
O3W—H5W···O3iv	0.85	2.19	2.794 (7)	128
O3W—H6W···O3v	0.85	1.96	2.770 (6)	160
O4W—H7W···O3W	0.85	1.78	2.620 (8)	169
O4W—H8W···O7vi	0.85	2.05	2.904 (6)	180
O5W—H9W···O5vi	0.87	2.01	2.841 (5)	159
O5W—H10W···O4vii	0.85	1.95	2.778 (5)	163
O6W—H11W···O3Wvii	0.85	1.87	2.679 (8)	160
O6W—H12W···O5Wviii	0.85	2.22	2.850 (5)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4W	0.86	1.89	2.747 (5)	172
N4—H4⋯O6W	0.86	1.90	2.729 (5)	161
O1—H1⋯O4	0.82 (3)	1.67 (3)	2.490 (5)	172 (7)
O7—H7⋯O6	0.82 (4)	1.63 (4)	2.440 (5)	171 (8)
O1W—H1W⋯O5Wi	0.85	2.27	2.654 (5)	108
O1W—H2W⋯O8ii	0.85	1.90	2.737 (5)	168
O2W—H3W⋯O8iii	0.84	2.08	2.852 (5)	152
O2W—H4W⋯O2iv	0.86	1.99	2.818 (5)	163
O3W—H5W⋯O3iv	0.85	2.19	2.794 (7)	128
O3W—H6W⋯O3v	0.85	1.96	2.770 (6)	160
O4W—H7W⋯O3W	0.85	1.78	2.620 (8)	169
O4W—H8W⋯O7vi	0.85	2.05	2.904 (6)	180
O5W—H9W⋯O5vi	0.87	2.01	2.841 (5)	159
O5W—H10W⋯O4vii	0.85	1.95	2.778 (5)	163
O6W—H11W⋯O3Wvii	0.85	1.87	2.679 (8)	160
O6W—H12W⋯O5Wviii	0.85	2.22	2.850 (5)	130

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