Bis(2,2'-bipyridine-κN,N')bis-(1H-indole-2-carboxyl-ato-κO,O')cadmium-2,2'-bipyridine-water (1/0.5/2).

The asymmetric unit of title compound, [Cd(C(9)H(6)NO(2))(2)(C(10)H(8)N(2))(2)]·0.5C(10)H(8)N(2)·2H(2)O, consists of one complex mol-ecule, one half of an uncoordinated 2,2'-bipyridine mol-ecule and two solvent water mol-ecules. The uncoordinated 2,2'-bipyridine mol-ecule is located on a center of symmetry. Within the complex mol-ecule, the Cd(II) atom is coordinated by four N atoms from two 2,2'-bipyridine ligands and three O atoms from two 1H-indole-2-carboxyl-ate anion ligands, completing a distorted CdN(4)O(3) penta-gonal bipyra-mid. The mol-ecules are assembled into one-dimensional chains along the [100] direction through classical hydrogen bonds (O-H⋯N, N-H⋯O and O-H⋯O). The resulting chains are further connected into two-dimensional supra-molecular layers parallel to the (110) direction by inter-molecular classical hydrogen bonds (N-H⋯O and O-H⋯O) from adjacent chains. A three-dimensional supra-molecular network is formed via interlayer and O-H⋯O hydrogen bonds.

Related literature

For general background, see: Dillon et al. (2003 ▶). For related cadmium(II) complexes with bipyridine and 1,10-phenanthroline ligands, see: Zhang et al. (2005 ▶); Lou & Zhang (2007 ▶).

Experimental

Crystal data

[Cd(C9H6NO2)2(C10H8N2)2]·0.5C10H8N2·2H2O

M = 859.19

Triclinic,

a = 11.513 (2) Å

b = 12.945 (3) Å

c = 14.302 (3) Å

α = 114.95 (3)°

β = 94.27 (3)°

γ = 93.84 (3)°

V = 1915.8 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.63 mm−1

T = 290 K

0.26 × 0.19 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.865, T max = 0.963

15180 measured reflections

6724 independent reflections

4444 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.106

S = 1.17

6724 reflections

515 parameters

H-atom parameters constrained

Δρmax = 1.26 e Å−3

Δρmin = −1.55 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg & Putz, 2004 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021064/rk2274sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021064/rk2274Isup2.hkl

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

[Cd(C9H6NO2)2(C10H8N2)2]·0.5C10H8N2·2H2O	Z = 2
Mr = 859.19	F(000) = 878
Triclinic, P1	Dx = 1.489 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.513 (2) Å	Cell parameters from 10384 reflections
b = 12.945 (3) Å	θ = 3.2–25°
c = 14.302 (3) Å	µ = 0.63 mm−1
α = 114.95 (3)°	T = 290 K
β = 94.27 (3)°	Block, colourless
γ = 93.84 (3)°	0.26 × 0.19 × 0.06 mm
V = 1915.8 (9) Å3

Rigaku R-AXIS RAPID diffractometer	6724 independent reflections
Radiation source: fine-focus sealed tube	4444 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→12
Tmin = 0.865, Tmax = 0.963	k = −15→15
15180 measured reflections	l = −16→16

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.P)2 + 4.4876P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
6724 reflections	Δρmax = 1.26 e Å−3
515 parameters	Δρmin = −1.55 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.36632 (4)	0.14575 (4)	0.19144 (3)	0.03937 (15)
N1	0.3953 (4)	0.3521 (4)	0.2404 (4)	0.0463 (12)
N2	0.3905 (4)	0.1847 (4)	0.0463 (3)	0.0414 (11)
N3	0.2855 (4)	0.2010 (4)	0.3542 (3)	0.0421 (11)
N4	0.1600 (4)	0.1689 (4)	0.1760 (4)	0.0512 (13)
N5	0.7181 (4)	0.2314 (4)	0.4379 (3)	0.0427 (11)
H5C	0.6805	0.1670	0.4272	0.051*
N6	0.2909 (4)	−0.2837 (4)	−0.0315 (3)	0.0460 (12)
H6C	0.3187	−0.2581	−0.0727	0.055*
N7	−0.1248 (4)	0.9667 (5)	0.4058 (4)	0.0660 (15)
O1	0.5438 (3)	0.1593 (3)	0.2739 (3)	0.0506 (10)
O2	0.6372 (3)	0.2675 (4)	0.2080 (3)	0.0620 (12)
O3	0.3234 (4)	−0.0430 (3)	0.2186 (3)	0.0583 (11)
O4	0.3252 (3)	−0.0426 (3)	0.0641 (3)	0.0558 (11)
O5	0.6427 (3)	1.0228 (3)	0.4546 (3)	0.0622 (12)
H5A	0.5887	0.9811	0.4117	0.093*
H5B	0.7061	0.9968	0.4473	0.093*
O6	0.4400 (4)	0.8833 (4)	0.3526 (3)	0.0711 (13)
H6A	0.3978	0.9092	0.3991	0.107*
H6B	0.4082	0.9014	0.3094	0.107*
C1	0.3993 (5)	0.4320 (5)	0.3376 (5)	0.0562 (17)
H1	0.3943	0.4085	0.3905	0.067*
C2	0.4103 (5)	0.5467 (6)	0.3634 (5)	0.0623 (18)
H2	0.4143	0.6000	0.4323	0.075*
C3	0.4153 (6)	0.5814 (5)	0.2856 (6)	0.0674 (19)
H3	0.4206	0.6588	0.3004	0.081*
C4	0.4124 (5)	0.4995 (6)	0.1847 (5)	0.0623 (18)
H4	0.4159	0.5215	0.1309	0.075*
C5	0.4043 (5)	0.3852 (5)	0.1639 (5)	0.0429 (14)
C6	0.4060 (4)	0.2936 (5)	0.0575 (4)	0.0413 (14)
C7	0.4251 (5)	0.3177 (6)	−0.0262 (5)	0.0568 (17)
H7	0.4340	0.3933	−0.0172	0.068*
C8	0.4309 (5)	0.2301 (6)	−0.1221 (5)	0.0570 (17)
H8	0.4443	0.2457	−0.1784	0.068*
C9	0.4166 (5)	0.1195 (6)	−0.1335 (5)	0.0501 (15)
H9	0.4205	0.0587	−0.1976	0.060*
C10	0.3961 (4)	0.0996 (5)	−0.0480 (5)	0.0464 (15)
H10	0.3857	0.0243	−0.0562	0.056*
C11	0.3500 (5)	0.2125 (5)	0.4401 (5)	0.0542 (16)
H11	0.4272	0.1958	0.4352	0.065*
C12	0.3092 (6)	0.2475 (6)	0.5350 (5)	0.0668 (19)
H12	0.3571	0.2540	0.5930	0.080*
C13	0.1967 (7)	0.2724 (6)	0.5417 (5)	0.070 (2)
H13	0.1667	0.2984	0.6054	0.084*
C14	0.1268 (6)	0.2589 (6)	0.4539 (5)	0.0622 (18)
H14	0.0492	0.2747	0.4579	0.075*
C15	0.1731 (5)	0.2216 (4)	0.3596 (4)	0.0415 (14)
C16	0.1037 (5)	0.2016 (5)	0.2606 (4)	0.0435 (14)
C17	−0.0148 (5)	0.2143 (6)	0.2558 (6)	0.0626 (18)
H17	−0.0530	0.2360	0.3151	0.075*
C18	−0.0748 (6)	0.1945 (7)	0.1626 (6)	0.083 (2)
H18	−0.1545	0.2021	0.1582	0.099*
C19	−0.0180 (6)	0.1636 (8)	0.0765 (6)	0.099 (3)
H19	−0.0570	0.1515	0.0129	0.119*
C20	0.1004 (5)	0.1506 (7)	0.0866 (5)	0.085 (3)
H20	0.1396	0.1280	0.0278	0.101*
C21	0.6248 (5)	0.2348 (5)	0.2767 (4)	0.0424 (14)
C22	0.7075 (4)	0.2856 (5)	0.3740 (4)	0.0406 (14)
C23	0.7796 (4)	0.3861 (5)	0.4152 (4)	0.0446 (14)
H23	0.7892	0.4380	0.3864	0.054*
C24	0.8374 (4)	0.3962 (5)	0.5108 (4)	0.0410 (14)
C25	0.9183 (5)	0.4786 (5)	0.5900 (5)	0.0546 (16)
H25	0.9451	0.5456	0.5856	0.066*
C26	0.9571 (5)	0.4596 (6)	0.6732 (5)	0.0598 (18)
H26	1.0104	0.5143	0.7256	0.072*
C27	0.9183 (5)	0.3594 (6)	0.6811 (5)	0.0600 (18)
H27	0.9473	0.3480	0.7381	0.072*
C28	0.8382 (5)	0.2776 (5)	0.6066 (5)	0.0538 (16)
H28	0.8114	0.2115	0.6126	0.065*
C29	0.7985 (4)	0.2967 (5)	0.5217 (4)	0.0400 (13)
C31	0.3117 (5)	−0.0931 (5)	0.1209 (5)	0.0449 (14)
C32	0.2787 (4)	−0.2191 (5)	0.0709 (4)	0.0392 (13)
C33	0.2308 (5)	−0.2888 (5)	0.1117 (5)	0.0524 (16)
H33	0.2147	−0.2664	0.1799	0.063*
C34	0.2103 (5)	−0.4011 (5)	0.0308 (4)	0.0480 (15)
C35	0.1611 (5)	−0.5075 (5)	0.0239 (5)	0.0614 (18)
H35	0.1328	−0.5130	0.0810	0.074*
C36	0.1561 (6)	−0.6015 (6)	−0.0683 (6)	0.074 (2)
H36	0.1226	−0.6717	−0.0742	0.088*
C37	0.1997 (6)	−0.5951 (6)	−0.1537 (6)	0.070 (2)
H37	0.1962	−0.6615	−0.2151	0.084*
C38	0.2484 (6)	−0.4927 (6)	−0.1504 (5)	0.0606 (17)
H38	0.2776	−0.4890	−0.2079	0.073*
C39	0.2515 (5)	−0.3961 (5)	−0.0576 (4)	0.0441 (14)
C41	−0.1487 (6)	0.9382 (7)	0.3045 (6)	0.083 (2)
H41	−0.2270	0.9264	0.2776	0.100*
C42	−0.0659 (7)	0.9251 (6)	0.2373 (6)	0.077 (2)
H42	−0.0875	0.9037	0.1671	0.092*
C43	0.0489 (6)	0.9446 (5)	0.2767 (5)	0.0643 (18)
H43	0.1077	0.9376	0.2339	0.077*
C44	0.0766 (5)	0.9749 (5)	0.3810 (5)	0.0550 (16)
H44	0.1547	0.9888	0.4090	0.066*
C45	−0.0117 (5)	0.9847 (5)	0.4443 (4)	0.0465 (15)

	U11	U22	U33	U12	U13	U23
Cd1	0.0375 (2)	0.0444 (3)	0.0352 (2)	0.00611 (17)	0.00440 (16)	0.01586 (19)
N1	0.049 (3)	0.040 (3)	0.050 (3)	0.009 (2)	0.009 (2)	0.019 (3)
N2	0.042 (3)	0.044 (3)	0.036 (3)	0.009 (2)	0.005 (2)	0.015 (2)
N3	0.051 (3)	0.045 (3)	0.027 (3)	0.007 (2)	0.008 (2)	0.011 (2)
N4	0.035 (3)	0.075 (4)	0.043 (3)	0.014 (2)	0.006 (2)	0.023 (3)
N5	0.048 (3)	0.042 (3)	0.037 (3)	0.000 (2)	−0.002 (2)	0.018 (2)
N6	0.053 (3)	0.051 (3)	0.034 (3)	0.006 (2)	0.005 (2)	0.019 (3)
N7	0.047 (3)	0.085 (4)	0.063 (4)	0.000 (3)	−0.002 (3)	0.031 (3)
O1	0.042 (2)	0.050 (3)	0.056 (3)	0.0005 (19)	−0.0068 (19)	0.022 (2)
O2	0.048 (2)	0.101 (4)	0.048 (3)	0.000 (2)	0.006 (2)	0.044 (3)
O3	0.071 (3)	0.044 (3)	0.050 (3)	0.001 (2)	0.010 (2)	0.011 (2)
O4	0.063 (3)	0.047 (3)	0.070 (3)	0.007 (2)	0.010 (2)	0.036 (2)
O5	0.051 (2)	0.071 (3)	0.068 (3)	0.002 (2)	0.001 (2)	0.035 (3)
O6	0.083 (3)	0.072 (3)	0.054 (3)	−0.004 (3)	0.005 (2)	0.026 (3)
C1	0.069 (4)	0.047 (4)	0.044 (4)	0.008 (3)	0.019 (3)	0.009 (3)
C2	0.062 (4)	0.048 (4)	0.061 (5)	0.009 (3)	0.017 (3)	0.007 (4)
C3	0.074 (5)	0.033 (4)	0.088 (6)	0.008 (3)	0.013 (4)	0.018 (4)
C4	0.068 (4)	0.053 (4)	0.065 (5)	0.010 (3)	0.011 (3)	0.024 (4)
C5	0.039 (3)	0.037 (4)	0.055 (4)	0.010 (3)	0.003 (3)	0.022 (3)
C6	0.035 (3)	0.049 (4)	0.046 (4)	0.007 (3)	0.005 (3)	0.026 (3)
C7	0.064 (4)	0.056 (4)	0.061 (4)	0.007 (3)	0.009 (3)	0.035 (4)
C8	0.071 (4)	0.069 (5)	0.039 (4)	0.014 (4)	0.012 (3)	0.029 (4)
C9	0.045 (3)	0.063 (4)	0.042 (4)	0.018 (3)	0.008 (3)	0.021 (3)
C10	0.042 (3)	0.054 (4)	0.049 (4)	0.008 (3)	0.005 (3)	0.027 (3)
C11	0.059 (4)	0.062 (4)	0.040 (4)	0.007 (3)	0.009 (3)	0.020 (3)
C12	0.084 (5)	0.074 (5)	0.043 (4)	0.004 (4)	0.006 (4)	0.027 (4)
C13	0.098 (6)	0.070 (5)	0.046 (4)	0.023 (4)	0.029 (4)	0.023 (4)
C14	0.061 (4)	0.071 (5)	0.056 (4)	0.023 (4)	0.026 (3)	0.023 (4)
C15	0.044 (3)	0.034 (3)	0.046 (4)	0.007 (3)	0.017 (3)	0.014 (3)
C16	0.040 (3)	0.038 (3)	0.049 (4)	0.007 (3)	0.010 (3)	0.014 (3)
C17	0.039 (3)	0.076 (5)	0.076 (5)	0.016 (3)	0.018 (3)	0.031 (4)
C18	0.045 (4)	0.120 (7)	0.092 (6)	0.020 (4)	0.006 (4)	0.054 (6)
C19	0.052 (5)	0.179 (9)	0.074 (6)	0.018 (5)	−0.008 (4)	0.064 (6)
C20	0.046 (4)	0.156 (8)	0.053 (5)	0.018 (4)	0.001 (3)	0.045 (5)
C21	0.036 (3)	0.048 (4)	0.046 (4)	0.019 (3)	0.007 (3)	0.020 (3)
C22	0.033 (3)	0.055 (4)	0.035 (3)	0.009 (3)	0.007 (2)	0.019 (3)
C23	0.039 (3)	0.049 (4)	0.049 (4)	0.000 (3)	0.007 (3)	0.025 (3)
C24	0.035 (3)	0.044 (4)	0.043 (4)	0.003 (3)	0.006 (3)	0.018 (3)
C25	0.056 (4)	0.050 (4)	0.053 (4)	−0.007 (3)	0.001 (3)	0.020 (3)
C26	0.057 (4)	0.063 (5)	0.046 (4)	−0.012 (3)	−0.004 (3)	0.015 (4)
C27	0.050 (4)	0.076 (5)	0.053 (4)	−0.001 (3)	−0.007 (3)	0.030 (4)
C28	0.055 (4)	0.059 (4)	0.053 (4)	−0.002 (3)	−0.002 (3)	0.032 (4)
C29	0.037 (3)	0.047 (4)	0.037 (3)	0.002 (3)	0.004 (2)	0.020 (3)
C31	0.034 (3)	0.043 (4)	0.054 (4)	0.011 (3)	0.008 (3)	0.015 (3)
C32	0.042 (3)	0.037 (3)	0.037 (3)	0.008 (3)	0.008 (2)	0.013 (3)
C33	0.063 (4)	0.053 (4)	0.043 (4)	0.002 (3)	0.013 (3)	0.021 (3)
C34	0.048 (3)	0.046 (4)	0.044 (4)	0.004 (3)	0.003 (3)	0.015 (3)
C35	0.071 (4)	0.048 (4)	0.066 (5)	−0.004 (3)	0.009 (3)	0.027 (4)
C36	0.086 (5)	0.047 (5)	0.080 (6)	−0.005 (4)	−0.010 (4)	0.023 (4)
C37	0.094 (5)	0.043 (4)	0.057 (5)	0.008 (4)	−0.013 (4)	0.008 (4)
C38	0.075 (5)	0.062 (5)	0.039 (4)	0.013 (4)	−0.003 (3)	0.016 (4)
C39	0.046 (3)	0.045 (4)	0.036 (3)	0.003 (3)	−0.002 (3)	0.013 (3)
C41	0.058 (5)	0.114 (7)	0.067 (5)	−0.005 (4)	−0.007 (4)	0.033 (5)
C42	0.088 (6)	0.080 (6)	0.053 (5)	0.002 (4)	−0.001 (4)	0.022 (4)
C43	0.079 (5)	0.055 (4)	0.061 (5)	0.014 (4)	0.017 (4)	0.024 (4)
C44	0.048 (4)	0.052 (4)	0.070 (5)	0.007 (3)	0.007 (3)	0.030 (4)
C45	0.045 (3)	0.041 (4)	0.054 (4)	0.001 (3)	0.002 (3)	0.022 (3)

Cd1—O1	2.239 (4)	C12—H12	0.9300
Cd1—O4	2.336 (4)	C13—C14	1.378 (9)
Cd1—N2	2.364 (4)	C13—H13	0.9300
Cd1—N3	2.408 (4)	C14—C15	1.389 (7)
Cd1—N4	2.419 (4)	C14—H14	0.9300
Cd1—N1	2.450 (5)	C15—C16	1.484 (8)
Cd1—O3	2.653 (4)	C16—C17	1.385 (7)
N1—C1	1.333 (7)	C17—C18	1.368 (9)
N1—C5	1.340 (7)	C17—H17	0.9300
N2—C10	1.344 (7)	C18—C19	1.357 (9)
N2—C6	1.347 (7)	C18—H18	0.9300
N3—C11	1.333 (7)	C19—C20	1.388 (9)
N3—C15	1.341 (6)	C19—H19	0.9300
N4—C20	1.325 (7)	C20—H20	0.9300
N4—C16	1.335 (7)	C21—C22	1.491 (7)
N5—C22	1.371 (6)	C22—C23	1.365 (7)
N5—C29	1.372 (6)	C23—C24	1.425 (7)
N5—H5C	0.8600	C23—H23	0.9300
N6—C32	1.370 (6)	C24—C25	1.407 (7)
N6—C39	1.375 (7)	C24—C29	1.410 (7)
N6—H6C	0.8600	C25—C26	1.364 (8)
N7—C41	1.336 (8)	C25—H25	0.9300
N7—C45	1.341 (7)	C26—C27	1.395 (8)
O1—C21	1.290 (6)	C26—H26	0.9300
O2—C21	1.236 (6)	C27—C28	1.371 (8)
O3—C31	1.261 (7)	C27—H27	0.9300
O4—C31	1.250 (7)	C28—C29	1.389 (7)
O5—H5A	0.8200	C28—H28	0.9300
O5—H5B	0.8200	C31—C32	1.486 (7)
O6—H6A	0.8200	C32—C33	1.372 (7)
O6—H6B	0.8200	C33—C34	1.415 (8)
C1—C2	1.364 (8)	C33—H33	0.9300
C1—H1	0.9300	C34—C39	1.408 (7)
C2—C3	1.368 (9)	C34—C35	1.413 (8)
C2—H2	0.9300	C35—C36	1.359 (9)
C3—C4	1.380 (8)	C35—H35	0.9300
C3—H3	0.9300	C36—C37	1.387 (9)
C4—C5	1.376 (8)	C36—H36	0.9300
C4—H4	0.9300	C37—C38	1.384 (9)
C5—C6	1.486 (8)	C37—H37	0.9300
C6—C7	1.387 (7)	C38—C39	1.383 (8)
C7—C8	1.373 (8)	C38—H38	0.9300
C7—H7	0.9300	C41—C42	1.371 (9)
C8—C9	1.368 (8)	C41—H41	0.9300
C8—H8	0.9300	C42—C43	1.361 (9)
C9—C10	1.384 (7)	C42—H42	0.9300
C9—H9	0.9300	C43—C44	1.377 (8)
C10—H10	0.9300	C43—H43	0.9300
C11—C12	1.369 (8)	C44—C45	1.389 (8)
C11—H11	0.9300	C44—H44	0.9300
C12—C13	1.356 (9)	C45—C45i	1.468 (11)
O1—Cd1—O4	107.11 (14)	N3—C15—C14	120.3 (5)
O1—Cd1—N2	108.36 (14)	N3—C15—C16	116.3 (5)
O4—Cd1—N2	82.76 (15)	C14—C15—C16	123.4 (5)
O1—Cd1—N3	89.13 (15)	N4—C16—C17	121.4 (6)
O4—Cd1—N3	119.52 (14)	N4—C16—C15	117.2 (5)
N2—Cd1—N3	146.91 (16)	C17—C16—C15	121.4 (5)
O1—Cd1—N4	156.39 (15)	C18—C17—C16	119.2 (6)
O4—Cd1—N4	89.06 (16)	C18—C17—H17	120.4
N2—Cd1—N4	90.32 (16)	C16—C17—H17	120.4
N3—Cd1—N4	67.69 (16)	C19—C18—C17	119.9 (6)
O1—Cd1—N1	89.04 (15)	C19—C18—H18	120.0
O4—Cd1—N1	150.16 (15)	C17—C18—H18	120.0
N2—Cd1—N1	68.19 (16)	C18—C19—C20	117.8 (7)
N3—Cd1—N1	84.76 (16)	C18—C19—H19	121.1
N4—Cd1—N1	84.58 (16)	C20—C19—H19	121.1
O1—Cd1—O3	84.88 (14)	N4—C20—C19	123.2 (6)
O4—Cd1—O3	52.23 (13)	N4—C20—H20	118.4
N2—Cd1—O3	134.85 (15)	C19—C20—H20	118.4
N3—Cd1—O3	72.87 (14)	O2—C21—O1	125.9 (5)
N4—Cd1—O3	92.11 (15)	O2—C21—C22	119.4 (5)
N1—Cd1—O3	156.86 (15)	O1—C21—C22	114.6 (5)
C1—N1—C5	118.9 (5)	C23—C22—N5	109.8 (5)
C1—N1—Cd1	123.7 (4)	C23—C22—C21	129.4 (5)
C5—N1—Cd1	117.4 (4)	N5—C22—C21	120.8 (5)
C10—N2—C6	118.2 (5)	C22—C23—C24	106.9 (5)
C10—N2—Cd1	121.1 (4)	C22—C23—H23	126.5
C6—N2—Cd1	120.6 (4)	C24—C23—H23	126.5
C11—N3—C15	118.6 (5)	C25—C24—C29	118.0 (5)
C11—N3—Cd1	121.7 (4)	C25—C24—C23	135.2 (5)
C15—N3—Cd1	119.7 (4)	C29—C24—C23	106.8 (5)
C20—N4—C16	118.5 (5)	C26—C25—C24	119.6 (6)
C20—N4—Cd1	122.5 (4)	C26—C25—H25	120.2
C16—N4—Cd1	119.1 (4)	C24—C25—H25	120.2
C22—N5—C29	108.8 (4)	C25—C26—C27	121.1 (6)
C22—N5—H5C	125.6	C25—C26—H26	119.4
C29—N5—H5C	125.6	C27—C26—H26	119.4
C32—N6—C39	109.0 (5)	C28—C27—C26	121.3 (6)
C32—N6—H6C	125.5	C28—C27—H27	119.3
C39—N6—H6C	125.5	C26—C27—H27	119.3
C41—N7—C45	117.4 (6)	C27—C28—C29	117.7 (6)
C21—O1—Cd1	119.1 (3)	C27—C28—H28	121.1
C31—O3—Cd1	84.5 (3)	C29—C28—H28	121.1
C31—O4—Cd1	99.5 (4)	N5—C29—C28	130.1 (5)
H5A—O5—H5B	114.5	N5—C29—C24	107.7 (5)
H6A—O6—H6B	100.4	C28—C29—C24	122.3 (5)
N1—C1—C2	123.1 (6)	O4—C31—O3	123.7 (6)
N1—C1—H1	118.4	O4—C31—C32	118.5 (5)
C2—C1—H1	118.4	O3—C31—C32	117.7 (5)
C1—C2—C3	118.5 (6)	N6—C32—C33	109.2 (5)
C1—C2—H2	120.7	N6—C32—C31	121.3 (5)
C3—C2—H2	120.7	C33—C32—C31	129.6 (5)
C2—C3—C4	118.9 (6)	C32—C33—C34	107.4 (5)
C2—C3—H3	120.6	C32—C33—H33	126.3
C4—C3—H3	120.6	C34—C33—H33	126.3
C5—C4—C3	119.9 (6)	C39—C34—C35	119.1 (6)
C5—C4—H4	120.0	C39—C34—C33	106.9 (5)
C3—C4—H4	120.0	C35—C34—C33	134.1 (6)
N1—C5—C4	120.6 (6)	C36—C35—C34	118.5 (6)
N1—C5—C6	117.1 (5)	C36—C35—H35	120.8
C4—C5—C6	122.3 (6)	C34—C35—H35	120.8
N2—C6—C7	121.1 (5)	C35—C36—C37	121.5 (6)
N2—C6—C5	116.5 (5)	C35—C36—H36	119.3
C7—C6—C5	122.3 (5)	C37—C36—H36	119.3
C8—C7—C6	120.1 (6)	C38—C37—C36	122.0 (6)
C8—C7—H7	119.9	C38—C37—H37	119.0
C6—C7—H7	119.9	C36—C37—H37	119.0
C9—C8—C7	118.9 (6)	C39—C38—C37	117.0 (6)
C9—C8—H8	120.6	C39—C38—H38	121.5
C7—C8—H8	120.6	C37—C38—H38	121.5
C8—C9—C10	119.0 (6)	N6—C39—C38	130.4 (6)
C8—C9—H9	120.5	N6—C39—C34	107.6 (5)
C10—C9—H9	120.5	C38—C39—C34	122.0 (6)
N2—C10—C9	122.7 (6)	N7—C41—C42	124.7 (7)
N2—C10—H10	118.7	N7—C41—H41	117.6
C9—C10—H10	118.7	C42—C41—H41	117.6
N3—C11—C12	123.9 (6)	C43—C42—C41	117.8 (7)
N3—C11—H11	118.1	C43—C42—H42	121.1
C12—C11—H11	118.1	C41—C42—H42	121.1
C13—C12—C11	117.8 (6)	C42—C43—C44	119.0 (6)
C13—C12—H12	121.1	C42—C43—H43	120.5
C11—C12—H12	121.1	C44—C43—H43	120.5
C12—C13—C14	119.9 (6)	C43—C44—C45	120.2 (6)
C12—C13—H13	120.1	C43—C44—H44	119.9
C14—C13—H13	120.1	C45—C44—H44	119.9
C13—C14—C15	119.5 (6)	N7—C45—C44	120.8 (6)
C13—C14—H14	120.2	N7—C45—C45i	116.2 (6)
C15—C14—H14	120.2	C44—C45—C45i	122.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···O5ii	0.86	2.09	2.892 (9)	155
N6—H6C···O2iii	0.86	2.00	2.801 (8)	156
O5—H5A···O6	0.82	1.96	2.748 (8)	161
O5—H5B···N7iv	0.82	2.09	2.879 (8)	161
O6—H6A···O5v	0.82	2.01	2.781 (7)	156
O6—H6B···O3vi	0.82	1.95	2.778 (6)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5C⋯O5i	0.86	2.09	2.892 (9)	155
N6—H6C⋯O2ii	0.86	2.00	2.801 (8)	156
O5—H5A⋯O6	0.82	1.96	2.748 (8)	161
O5—H5B⋯N7iii	0.82	2.09	2.879 (8)	161
O6—H6A⋯O5iv	0.82	2.01	2.781 (7)	156
O6—H6B⋯O3v	0.82	1.95	2.778 (6)	174

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