Diaqua-bis-(5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ato-κN,O)cadmium N,N-dimethyl-formamide disolvate.

In the title complex, [Cd(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the six-coordinate Cd(II) ion is in a slightly distorted octa-hedral environment, defined by two O atoms from two coordinated water mol-ecules and two carboxyl-ate O atoms and two N atoms from two N,O-bidentate 5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ate ligands. In the crystal, complex mol-ecules and dimethyl-formamide solvent mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds into a two-dimensional supra-molecular structure. The propyl groups of the ligands are disordered over two conformations with refined occupancies of 0.680 (7) and 0.320 (7).

Related literature

For our past work based on the H3PIDC (2-propyl-imidazol-4,5-dicarb­oxy­lic acid) ligand, see: Fan et al. (2010 ▶); Li, Song, Miao, Tong et al. (2011 ▶); Li, Miao et al. (2010 ▶); Li, Yan et al. (2010 ▶); Song et al. (2010 ▶); He et al. (2010 ▶); Yan et al. (2010 ▶). For our past work based on the H3EIDC (2-ethyl-1H-imidazol-4,5-dicarb­oxy­lic acid) ligand, see: Li, Ma et al. (2011 ▶); Li, Song, Miao, Hu et al. (2011 ▶).

Experimental

Crystal data

[Cd(C8H9N2O4)2(H2O)2]·2C3H7NO

M = 688.97

Orthorhombic,

a = 16.6040 (14) Å

b = 9.8516 (8) Å

c = 18.4154 (16) Å

V = 3012.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 295 K

0.27 × 0.24 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.815, T max = 0.851

16187 measured reflections

4421 independent reflections

3111 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.079

S = 1.00

4421 reflections

444 parameters

233 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 1285 Friedel pairs

Flack parameter: −0.04 (4)

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811050264/pk2369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050264/pk2369Isup2.hkl

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

[Cd(C8H9N2O4)2(H2O)2]·2C3H7NO	F(000) = 1416
Mr = 688.97	Dx = 1.519 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3600 reflections
a = 16.6040 (14) Å	θ = 1.4–28°
b = 9.8516 (8) Å	µ = 0.79 mm−1
c = 18.4154 (16) Å	T = 295 K
V = 3012.3 (4) Å3	Block, colourless
Z = 4	0.27 × 0.24 × 0.21 mm

Rigaku/MSC Mercury CCD diffractometer	4421 independent reflections
Radiation source: fine-focus sealed tube	3111 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 26.3°, θmin = 2.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −20→20
Tmin = 0.815, Tmax = 0.851	k = −11→12
16187 measured reflections	l = −22→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.020P)2 + 3.2P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
4421 reflections	Δρmax = 0.41 e Å−3
444 parameters	Δρmin = −0.39 e Å−3
233 restraints	Absolute structure: Flack (1983), 1285 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (4)

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	0.61035 (2)	0.49830 (5)	0.52305 (9)	0.04966 (12)
O1	0.4830 (3)	1.1346 (4)	0.5670 (3)	0.0656 (16)
O2	0.5807 (3)	1.0620 (5)	0.6382 (3)	0.0668 (14)
H2	0.5962	0.9882	0.6534	0.080*
O3	0.6581 (3)	0.8521 (5)	0.6574 (3)	0.0677 (14)
O4	0.6630 (3)	0.6406 (4)	0.6142 (3)	0.0614 (13)
O5	0.7407 (3)	−0.1351 (4)	0.4749 (3)	0.0665 (16)
O6	0.6439 (3)	−0.0594 (5)	0.4016 (3)	0.0674 (14)
H6	0.6161	0.0092	0.3987	0.081*
O7	0.5653 (3)	0.1490 (4)	0.3846 (3)	0.0614 (13)
O8	0.5579 (2)	0.3569 (4)	0.4313 (3)	0.0572 (13)
O1W	0.7047 (3)	0.5956 (4)	0.4459 (4)	0.0730 (16)
H1W	0.748 (3)	0.554 (6)	0.440 (5)	0.110*
H2W	0.718 (4)	0.675 (3)	0.442 (5)	0.110*
O2W	0.5174 (3)	0.4033 (4)	0.6026 (3)	0.0662 (15)
H3W	0.519 (4)	0.325 (3)	0.590 (4)	0.099*
H4W	0.473 (2)	0.434 (6)	0.596 (5)	0.099*
N1	0.4706 (3)	0.8811 (4)	0.4998 (3)	0.0429 (15)
H1A	0.4358	0.9371	0.4826	0.051*
N2	0.5401 (2)	0.6945 (4)	0.5161 (4)	0.0391 (11)
N3	0.7518 (3)	0.1189 (5)	0.5425 (3)	0.0483 (17)
H3A	0.7873	0.0636	0.5592	0.058*
N4	0.6815 (2)	0.3026 (4)	0.5273 (4)	0.0418 (11)
C1	0.5241 (3)	0.9076 (5)	0.5542 (3)	0.0398 (14)
C2	0.5677 (3)	0.7909 (5)	0.5641 (3)	0.0396 (14)
C3	0.5277 (4)	1.0437 (6)	0.5882 (4)	0.0517 (18)
C4	0.6343 (4)	0.7584 (6)	0.6152 (4)	0.0527 (17)
C5	0.4819 (3)	0.7508 (5)	0.4775 (3)	0.0414 (14)
C6A	0.4334 (10)	0.686 (2)	0.4188 (5)	0.059 (3)	0.680 (7)
H6A	0.3842	0.7379	0.4119	0.071*	0.680 (7)
H6B	0.4183	0.5953	0.4338	0.071*	0.680 (7)
C7A	0.4787 (7)	0.6779 (11)	0.3461 (6)	0.076 (3)	0.680 (7)
H7A	0.5335	0.6477	0.3544	0.091*	0.680 (7)
H7B	0.4525	0.6126	0.3145	0.091*	0.680 (7)
C8A	0.4793 (9)	0.8133 (12)	0.3110 (7)	0.105 (4)	0.680 (7)
H8A	0.4993	0.8050	0.2623	0.158*	0.680 (7)
H8B	0.5134	0.8735	0.3380	0.158*	0.680 (7)
H8C	0.4255	0.8491	0.3098	0.158*	0.680 (7)
C6B	0.439 (2)	0.676 (4)	0.4189 (8)	0.065 (4)	0.320 (7)
H6C	0.3824	0.6690	0.4324	0.077*	0.320 (7)
H6D	0.4603	0.5846	0.4167	0.077*	0.320 (7)
C7B	0.4436 (13)	0.738 (3)	0.3427 (13)	0.080 (3)	0.320 (7)
H7C	0.4013	0.7008	0.3124	0.096*	0.320 (7)
H7D	0.4354	0.8358	0.3458	0.096*	0.320 (7)
C8B	0.5227 (14)	0.710 (3)	0.3096 (14)	0.105 (6)	0.320 (7)
H8D	0.5154	0.6838	0.2598	0.157*	0.320 (7)
H8E	0.5487	0.6379	0.3357	0.157*	0.320 (7)
H8F	0.5556	0.7902	0.3118	0.157*	0.320 (7)
C9	0.6991 (3)	0.0907 (5)	0.4879 (3)	0.0409 (15)
C10	0.6547 (3)	0.2079 (5)	0.4781 (3)	0.0399 (14)
C11	0.7400 (3)	0.2446 (5)	0.5661 (3)	0.0434 (15)
C12	0.6953 (4)	−0.0449 (6)	0.4524 (4)	0.0501 (17)
C13	0.5881 (4)	0.2408 (6)	0.4287 (4)	0.0467 (16)
C14A	0.7785 (8)	0.3070 (14)	0.6317 (5)	0.075 (3)	0.680 (7)
H14A	0.7634	0.4018	0.6353	0.091*	0.680 (7)
H14B	0.8367	0.3017	0.6276	0.091*	0.680 (7)
C15A	0.7501 (10)	0.2293 (14)	0.7006 (7)	0.108 (3)	0.680 (7)
H15A	0.6917	0.2293	0.7027	0.129*	0.680 (7)
H15B	0.7682	0.1358	0.6982	0.129*	0.680 (7)
C16A	0.7827 (10)	0.2939 (17)	0.7661 (6)	0.132 (4)	0.680 (7)
H16A	0.7636	0.2465	0.8083	0.199*	0.680 (7)
H16B	0.7653	0.3867	0.7681	0.199*	0.680 (7)
H16C	0.8404	0.2906	0.7648	0.199*	0.680 (7)
C14B	0.7994 (14)	0.320 (3)	0.6113 (10)	0.068 (4)	0.320 (7)
H14C	0.7917	0.4168	0.6047	0.081*	0.320 (7)
H14D	0.8536	0.2976	0.5955	0.081*	0.320 (7)
C15B	0.7901 (14)	0.284 (3)	0.6922 (12)	0.093 (4)	0.320 (7)
H15C	0.7966	0.1874	0.6990	0.112*	0.320 (7)
H15D	0.8312	0.3305	0.7203	0.112*	0.320 (7)
C16B	0.7095 (15)	0.327 (3)	0.7171 (14)	0.113 (6)	0.320 (7)
H16D	0.7064	0.3180	0.7689	0.169*	0.320 (7)
H16E	0.6693	0.2702	0.6949	0.169*	0.320 (7)
H16F	0.7003	0.4196	0.7037	0.169*	0.320 (7)
O9	0.3702 (2)	0.5396 (4)	0.6089 (3)	0.0675 (14)
N5	0.3911 (3)	0.7234 (5)	0.6798 (3)	0.0514 (13)
C17	0.3557 (3)	0.6572 (5)	0.6270 (3)	0.0559 (19)
H17A	0.3162	0.7031	0.6009	0.067*
C18	0.3685 (3)	0.8631 (5)	0.6949 (3)	0.080 (2)
H18A	0.3248	0.8892	0.6637	0.119*
H18B	0.4138	0.9215	0.6864	0.119*
H18C	0.3519	0.8709	0.7447	0.119*
C19	0.4499 (5)	0.6607 (9)	0.7254 (5)	0.087 (3)
H19A	0.4500	0.5645	0.7170	0.131*
H19B	0.4371	0.6784	0.7753	0.131*
H19C	0.5022	0.6971	0.7145	0.131*
O10	0.8514 (2)	0.4647 (4)	0.4356 (3)	0.0676 (15)
N6	0.8302 (3)	0.2882 (5)	0.3600 (3)	0.0548 (14)
C20	0.8676 (4)	0.3505 (7)	0.4120 (4)	0.060 (2)
H20A	0.9104	0.3050	0.4336	0.072*
C21	0.7640 (4)	0.3522 (8)	0.3232 (5)	0.075 (2)
H21A	0.7836	0.4272	0.2951	0.112*
H21B	0.7258	0.3843	0.3583	0.112*
H21C	0.7384	0.2876	0.2917	0.112*
C22	0.8521 (5)	0.1525 (7)	0.3359 (5)	0.084 (3)
H22A	0.8067	0.0929	0.3416	0.126*
H22B	0.8962	0.1196	0.3646	0.126*
H22C	0.8676	0.1553	0.2857	0.126*

	U11	U22	U33	U12	U13	U23
Cd1	0.04830 (18)	0.02748 (15)	0.0732 (3)	0.00652 (16)	−0.0012 (3)	−0.0011 (2)
O1	0.060 (3)	0.033 (2)	0.104 (5)	0.009 (2)	0.004 (3)	−0.005 (2)
O2	0.079 (4)	0.040 (3)	0.082 (4)	0.000 (3)	0.002 (3)	−0.019 (3)
O3	0.080 (4)	0.054 (3)	0.069 (4)	0.003 (2)	−0.028 (3)	−0.015 (3)
O4	0.062 (3)	0.047 (3)	0.075 (4)	0.005 (2)	−0.024 (3)	0.003 (3)
O5	0.063 (3)	0.031 (2)	0.105 (5)	0.011 (2)	0.008 (3)	−0.005 (3)
O6	0.075 (4)	0.039 (3)	0.088 (4)	0.004 (3)	−0.011 (3)	−0.019 (3)
O7	0.070 (3)	0.048 (3)	0.067 (3)	−0.003 (2)	−0.015 (3)	−0.008 (2)
O8	0.060 (3)	0.038 (2)	0.074 (4)	0.010 (2)	−0.015 (3)	0.002 (2)
O1W	0.066 (3)	0.040 (3)	0.113 (5)	−0.001 (2)	0.022 (4)	−0.002 (3)
O2W	0.064 (3)	0.037 (2)	0.098 (4)	0.001 (2)	0.017 (3)	−0.005 (3)
N1	0.038 (3)	0.033 (2)	0.059 (4)	0.008 (2)	−0.001 (3)	0.008 (2)
N2	0.040 (2)	0.030 (2)	0.047 (3)	0.0019 (17)	−0.008 (3)	−0.007 (3)
N3	0.037 (3)	0.036 (2)	0.072 (5)	0.007 (2)	−0.002 (3)	0.012 (3)
N4	0.038 (2)	0.0281 (19)	0.059 (3)	0.0001 (17)	0.003 (3)	0.008 (3)
C1	0.037 (3)	0.031 (3)	0.052 (4)	0.002 (2)	0.004 (3)	0.000 (3)
C2	0.043 (3)	0.031 (3)	0.045 (4)	0.001 (2)	0.002 (3)	0.004 (3)
C3	0.047 (4)	0.035 (3)	0.073 (5)	−0.005 (3)	0.016 (4)	−0.007 (3)
C4	0.052 (4)	0.048 (4)	0.057 (5)	0.000 (3)	−0.010 (4)	0.008 (4)
C5	0.036 (3)	0.035 (3)	0.053 (4)	0.001 (3)	0.001 (3)	0.002 (3)
C6A	0.056 (4)	0.056 (4)	0.064 (5)	0.001 (4)	−0.011 (4)	−0.006 (4)
C7A	0.068 (5)	0.081 (5)	0.079 (5)	0.004 (4)	−0.009 (4)	−0.006 (4)
C8A	0.112 (7)	0.109 (6)	0.095 (7)	−0.021 (6)	0.006 (6)	0.017 (6)
C6B	0.061 (6)	0.064 (6)	0.069 (6)	0.002 (5)	−0.010 (5)	−0.005 (5)
C7B	0.079 (6)	0.081 (6)	0.080 (6)	−0.002 (5)	−0.007 (5)	−0.004 (5)
C8B	0.106 (9)	0.104 (9)	0.103 (9)	−0.006 (7)	−0.006 (8)	0.001 (8)
C9	0.045 (3)	0.025 (3)	0.053 (4)	−0.004 (2)	0.012 (3)	0.003 (3)
C10	0.043 (3)	0.033 (3)	0.044 (4)	0.004 (2)	0.004 (3)	0.002 (3)
C11	0.045 (4)	0.036 (3)	0.050 (4)	−0.001 (3)	0.003 (3)	−0.002 (3)
C12	0.045 (4)	0.034 (3)	0.071 (5)	−0.007 (3)	0.018 (4)	−0.007 (3)
C13	0.053 (4)	0.033 (3)	0.054 (5)	−0.002 (3)	0.005 (4)	−0.003 (3)
C14A	0.075 (5)	0.070 (5)	0.082 (5)	−0.004 (4)	−0.018 (5)	−0.009 (5)
C15A	0.108 (6)	0.119 (6)	0.097 (5)	−0.025 (5)	−0.002 (5)	−0.011 (5)
C16A	0.150 (8)	0.152 (8)	0.095 (5)	−0.016 (7)	−0.017 (6)	−0.010 (6)
C14B	0.068 (7)	0.067 (6)	0.067 (7)	−0.011 (6)	−0.012 (6)	−0.004 (6)
C15B	0.098 (6)	0.097 (6)	0.084 (6)	−0.022 (5)	−0.012 (6)	−0.008 (6)
C16B	0.122 (9)	0.114 (9)	0.102 (9)	−0.010 (8)	−0.011 (8)	−0.008 (8)
O9	0.052 (3)	0.053 (3)	0.098 (4)	−0.003 (2)	−0.003 (3)	−0.012 (3)
N5	0.045 (3)	0.050 (3)	0.059 (4)	−0.002 (3)	0.005 (3)	−0.002 (3)
C17	0.043 (4)	0.045 (4)	0.080 (6)	0.004 (3)	0.002 (4)	−0.006 (4)
C18	0.108 (6)	0.046 (4)	0.084 (6)	0.000 (4)	0.012 (5)	−0.013 (4)
C19	0.090 (6)	0.092 (6)	0.080 (7)	0.018 (5)	−0.010 (6)	−0.008 (5)
O10	0.049 (3)	0.053 (3)	0.101 (4)	−0.002 (2)	−0.013 (3)	−0.026 (3)
N6	0.056 (3)	0.051 (3)	0.058 (4)	−0.006 (3)	0.005 (3)	−0.011 (3)
C20	0.039 (3)	0.058 (4)	0.082 (6)	−0.001 (3)	−0.006 (4)	0.001 (4)
C21	0.058 (5)	0.090 (6)	0.076 (6)	0.017 (4)	−0.007 (4)	−0.019 (5)
C22	0.110 (7)	0.051 (4)	0.092 (7)	0.001 (4)	0.029 (6)	−0.011 (4)

Cd1—N4	2.262 (4)	C7B—H7D	0.9700
Cd1—N2	2.262 (4)	C8B—H8D	0.9600
Cd1—O2W	2.325 (6)	C8B—H8E	0.9600
Cd1—O1W	2.322 (5)	C8B—H8F	0.9600
Cd1—O4	2.356 (5)	C9—C10	1.381 (7)
Cd1—O8	2.357 (5)	C9—C12	1.489 (8)
O1—C3	1.227 (7)	C10—C13	1.468 (9)
O2—C3	1.287 (8)	C11—C14B	1.490 (9)
O2—H2	0.8200	C11—C14A	1.499 (8)
O3—C4	1.269 (8)	C14A—C15A	1.555 (11)
O4—C4	1.255 (7)	C14A—H14A	0.9700
O5—C12	1.236 (7)	C14A—H14B	0.9700
O6—C12	1.275 (8)	C15A—C16A	1.467 (11)
O6—H6	0.8200	C15A—H15A	0.9700
O7—C13	1.274 (7)	C15A—H15B	0.9700
O8—C13	1.251 (6)	C16A—H16A	0.9600
O1W—H1W	0.83 (2)	C16A—H16B	0.9600
O1W—H2W	0.82 (2)	C16A—H16C	0.9600
O2W—H3W	0.80 (2)	C14B—C15B	1.537 (12)
O2W—H4W	0.80 (2)	C14B—H14C	0.9700
N1—C5	1.360 (7)	C14B—H14D	0.9700
N1—C1	1.363 (7)	C15B—C16B	1.475 (12)
N1—H1A	0.8600	C15B—H15C	0.9700
N2—C5	1.321 (7)	C15B—H15D	0.9700
N2—C2	1.376 (7)	C16B—H16D	0.9600
N3—C11	1.327 (7)	C16B—H16E	0.9600
N3—C9	1.363 (7)	C16B—H16F	0.9600
N3—H3A	0.8600	O9—C17	1.229 (6)
N4—C11	1.334 (7)	N5—C17	1.311 (7)
N4—C10	1.375 (8)	N5—C19	1.429 (9)
C1—C2	1.372 (7)	N5—C18	1.454 (6)
C1—C3	1.480 (8)	C17—H17A	0.9300
C2—C4	1.486 (9)	C18—H18A	0.9600
C5—C6B	1.490 (9)	C18—H18B	0.9600
C5—C6A	1.492 (7)	C18—H18C	0.9600
C6A—C7A	1.537 (11)	C19—H19A	0.9600
C6A—H6A	0.9700	C19—H19B	0.9600
C6A—H6B	0.9700	C19—H19C	0.9600
C7A—C8A	1.483 (10)	O10—C20	1.235 (7)
C7A—H7A	0.9700	N6—C20	1.296 (8)
C7A—H7B	0.9700	N6—C21	1.436 (9)
C8A—H8A	0.9600	N6—C22	1.455 (8)
C8A—H8B	0.9600	C20—H20A	0.9300
C8A—H8C	0.9600	C21—H21A	0.9600
C6B—C7B	1.534 (12)	C21—H21B	0.9600
C6B—H6C	0.9700	C21—H21C	0.9600
C6B—H6D	0.9700	C22—H22A	0.9600
C7B—C8B	1.476 (12)	C22—H22B	0.9600
C7B—H7C	0.9700	C22—H22C	0.9600
N4—Cd1—N2	178.7 (3)	N3—C9—C10	105.6 (5)
N4—Cd1—O2W	88.96 (17)	N3—C9—C12	122.3 (5)
N2—Cd1—O2W	92.14 (18)	C10—C9—C12	132.1 (6)
N4—Cd1—O1W	91.17 (18)	N4—C10—C9	108.0 (5)
N2—Cd1—O1W	87.75 (17)	N4—C10—C13	120.1 (5)
O2W—Cd1—O1W	178.6 (2)	C9—C10—C13	131.8 (6)
N4—Cd1—O4	106.78 (19)	N3—C11—N4	109.4 (5)
N2—Cd1—O4	73.93 (18)	N3—C11—C14B	123.4 (14)
O2W—Cd1—O4	92.1 (2)	N4—C11—C14B	124.6 (14)
O1W—Cd1—O4	86.57 (18)	N3—C11—C14A	125.7 (8)
N4—Cd1—O8	73.39 (19)	N4—C11—C14A	124.5 (8)
N2—Cd1—O8	105.90 (17)	O5—C12—O6	125.0 (6)
O2W—Cd1—O8	88.21 (17)	O5—C12—C9	118.2 (7)
O1W—Cd1—O8	93.1 (2)	O6—C12—C9	116.8 (6)
O4—Cd1—O8	179.7 (2)	O8—C13—O7	123.6 (6)
C3—O2—H2	109.5	O8—C13—C10	118.8 (6)
C4—O4—Cd1	114.8 (4)	O7—C13—C10	117.6 (5)
C12—O6—H6	109.5	C11—C14A—C15A	109.1 (8)
C13—O8—Cd1	114.8 (4)	C11—C14A—H14A	109.9
Cd1—O1W—H1W	117 (6)	C15A—C14A—H14A	109.9
Cd1—O1W—H2W	129 (6)	C11—C14A—H14B	109.9
H1W—O1W—H2W	104 (4)	C15A—C14A—H14B	109.9
Cd1—O2W—H3W	101 (6)	H14A—C14A—H14B	108.3
Cd1—O2W—H4W	111 (6)	C16A—C15A—C14A	110.3 (10)
H3W—O2W—H4W	109 (4)	C16A—C15A—H15A	109.6
C5—N1—C1	108.2 (4)	C14A—C15A—H15A	109.6
C5—N1—H1A	125.9	C16A—C15A—H15B	109.6
C1—N1—H1A	125.9	C14A—C15A—H15B	109.6
C5—N2—C2	107.5 (4)	H15A—C15A—H15B	108.1
C5—N2—Cd1	140.0 (4)	C11—C14B—C15B	111.2 (16)
C2—N2—Cd1	112.4 (4)	C11—C14B—H14C	109.4
C11—N3—C9	109.7 (5)	C15B—C14B—H14C	109.4
C11—N3—H3A	125.2	C11—C14B—H14D	109.4
C9—N3—H3A	125.2	C15B—C14B—H14D	109.4
C11—N4—C10	107.3 (4)	H14C—C14B—H14D	108.0
C11—N4—Cd1	139.8 (5)	C16B—C15B—C14B	109.2 (11)
C10—N4—Cd1	112.8 (4)	C16B—C15B—H15C	109.8
N1—C1—C2	106.3 (5)	C14B—C15B—H15C	109.8
N1—C1—C3	120.7 (5)	C16B—C15B—H15D	109.8
C2—C1—C3	132.9 (6)	C14B—C15B—H15D	109.8
C1—C2—N2	108.4 (5)	H15C—C15B—H15D	108.3
C1—C2—C4	131.1 (6)	C15B—C16B—H16D	109.5
N2—C2—C4	120.5 (5)	C15B—C16B—H16E	109.5
O1—C3—O2	122.6 (6)	H16D—C16B—H16E	109.5
O1—C3—C1	120.1 (7)	C15B—C16B—H16F	109.5
O2—C3—C1	117.3 (6)	H16D—C16B—H16F	109.5
O4—C4—O3	124.2 (6)	H16E—C16B—H16F	109.5
O4—C4—C2	118.2 (6)	C17—N5—C19	121.9 (6)
O3—C4—C2	117.6 (5)	C17—N5—C18	119.9 (6)
N2—C5—N1	109.5 (5)	C19—N5—C18	118.2 (6)
N2—C5—C6B	122 (2)	O9—C17—N5	125.6 (5)
N1—C5—C6B	128 (2)	O9—C17—H17A	117.2
N2—C5—C6A	127.3 (10)	N5—C17—H17A	117.2
N1—C5—C6A	123.2 (10)	N5—C18—H18A	109.5
C5—C6A—C7A	113.0 (9)	N5—C18—H18B	109.5
C5—C6A—H6A	109.0	H18A—C18—H18B	109.5
C7A—C6A—H6A	109.0	N5—C18—H18C	109.5
C5—C6A—H6B	109.0	H18A—C18—H18C	109.5
C7A—C6A—H6B	109.0	H18B—C18—H18C	109.5
H6A—C6A—H6B	107.8	N5—C19—H19A	109.5
C8A—C7A—C6A	109.6 (10)	N5—C19—H19B	109.5
C8A—C7A—H7A	109.8	H19A—C19—H19B	109.5
C6A—C7A—H7A	109.8	N5—C19—H19C	109.5
C8A—C7A—H7B	109.8	H19A—C19—H19C	109.5
C6A—C7A—H7B	109.8	H19B—C19—H19C	109.5
H7A—C7A—H7B	108.2	C20—N6—C21	120.5 (6)
C5—C6B—C7B	116 (2)	C20—N6—C22	122.7 (7)
C5—C6B—H6C	108.3	C21—N6—C22	116.8 (6)
C7B—C6B—H6C	108.3	O10—C20—N6	125.9 (6)
C5—C6B—H6D	108.3	O10—C20—H20A	117.0
C7B—C6B—H6D	108.3	N6—C20—H20A	117.0
H6C—C6B—H6D	107.4	N6—C21—H21A	109.5
C8B—C7B—C6B	110.4 (12)	N6—C21—H21B	109.5
C8B—C7B—H7C	109.6	H21A—C21—H21B	109.5
C6B—C7B—H7C	109.6	N6—C21—H21C	109.5
C8B—C7B—H7D	109.6	H21A—C21—H21C	109.5
C6B—C7B—H7D	109.6	H21B—C21—H21C	109.5
H7C—C7B—H7D	108.1	N6—C22—H22A	109.5
C7B—C8B—H8D	109.5	N6—C22—H22B	109.5
C7B—C8B—H8E	109.5	H22A—C22—H22B	109.5
H8D—C8B—H8E	109.5	N6—C22—H22C	109.5
C7B—C8B—H8F	109.5	H22A—C22—H22C	109.5
H8D—C8B—H8F	109.5	H22B—C22—H22C	109.5
H8E—C8B—H8F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.69	2.460 (6)	155.
O6—H6···O7	0.82	1.64	2.453 (6)	174.
O1W—H1W···O10	0.83 (2)	1.94 (2)	2.763 (6)	175 (9)
O1W—H2W···O5i	0.82 (2)	2.00 (4)	2.771 (6)	158 (9)
O2W—H3W···O1ii	0.80 (2)	2.02 (3)	2.787 (6)	161 (7)
O2W—H4W···O9	0.80 (2)	2.02 (3)	2.791 (6)	162 (8)
N1—H1A···O10iii	0.86	1.91	2.761 (6)	170.
N3—H3A···O9iv	0.86	1.94	2.792 (6)	171.

Table 1

Selected bond lengths (Å)

Cd1—N4	2.262 (4)
Cd1—N2	2.262 (4)
Cd1—O2W	2.325 (6)
Cd1—O1W	2.322 (5)
Cd1—O4	2.356 (5)
Cd1—O8	2.357 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.69	2.460 (6)	155
O6—H6⋯O7	0.82	1.64	2.453 (6)	174
O1W—H1W⋯O10	0.83 (2)	1.94 (2)	2.763 (6)	175 (9)
O1W—H2W⋯O5i	0.82 (2)	2.00 (4)	2.771 (6)	158 (9)
O2W—H3W⋯O1ii	0.80 (2)	2.02 (3)	2.787 (6)	161 (7)
O2W—H4W⋯O9	0.80 (2)	2.02 (3)	2.791 (6)	162 (8)
N1—H1A⋯O10iii	0.86	1.91	2.761 (6)	170
N3—H3A⋯O9iv	0.86	1.94	2.792 (6)	171

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