Bis(2,2'-bipyridyl-κN,N')bis-(2-hydroxy-benzoato)-κO;κO,O-cadmium(II) methanol solvate.

The title compound, [Cd(C(7)H(5)O(3))(2)(C(10)H(8)N(2))(2)]·CH(3)OH, contains one monomeric seven-coordinate cadmium complex and one methanol solvate mol-ecule. The Cd(II) atom is coordinated to two 2,2'-bipyridyl ligands via the N atoms and to two salicylate anions (Hsal(-)) via the carboxyl-ate O atoms, which act as monodentate ligand for the one and bidentate ligand for the second. The Cd(II) atom exhibits a {6 + 1} environment, approximately described as a distorted capped octa-hedron with the apical positions occupied by one of the two N atoms belonging to one bipyridyl ligand and one of the two carboxyl-ate O atoms from the monodentate Hsal(-) ligand. Two intra-molecular six-membered hydrogen-bonded rings are present, generated from inter-actions between the carboxyl-ate and hydr-oxy groups of the salicylate ligands. There is one inter-molecular hydrogen-bonding inter-action involving the methanol solvent mol-ecule and the carboxyl-ate group from the monodentate Hsal(-) ligand. The crystal packing is governed by π-π stacking inter-actions [centroid-centroid distance = 3.783 (4) Å] which occur between bipyridyl ligands, by C-H⋯O and C-H⋯π inter-actions and by numerous van der Waals contacts.

Related literature

For related structures, see: Lemoine et al. (2004 ▶); Mazurier et al. (2000 ▶); Tomas et al. (2006 ▶); Turner et al. (1982 ▶). For the anti-inflammatory properties of zinc complexes, see: Sorensen (2002 ▶ and references therein).

Experimental

Crystal data

[Cd(C7H5O3)2(C10H8N2)2]·CH4O

M = 731.03

Triclinic,

a = 9.115 (4) Å

b = 12.189 (2) Å

c = 14.883 (2) Å

α = 97.64 (1)°

β = 92.30 (3)°

γ = 101.00 (3)°

V = 1605.1 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.74 mm−1

T = 293 K

0.40 × 0.18 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

9433 measured reflections

9117 independent reflections

4943 reflections with I > 2σ(I)

R int = 0.040

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 0.97

9117 reflections

423 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.85 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054610/dn2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054610/dn2517Isup2.hkl

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

[Cd(C7H5O3)2(C10H8N2)2]·CH4O	Z = 2
Mr = 731.03	F(000) = 744
Triclinic, P1	Dx = 1.513 Mg m−3Dm = 1.53 (2) Mg m−3Dm measured by flotation (CCl4/CH2Cl2)
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.115 (4) Å	Cell parameters from 25 reflections
b = 12.189 (2) Å	θ = 1.7–8.9°
c = 14.883 (2) Å	µ = 0.74 mm−1
α = 97.64 (1)°	T = 293 K
β = 92.30 (3)°	Parallelepiped, colourless
γ = 101.00 (3)°	0.40 × 0.18 × 0.13 mm
V = 1605.1 (8) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.040
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.1°
graphite	h = −12→12
ω–2θ scans	k = −17→16
9433 measured reflections	l = 0→20
9117 independent reflections	3 standard reflections every 60 min
4943 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
9117 reflections	(Δ/σ)max = 0.001
423 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.85 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	0.22853 (3)	0.25632 (3)	0.68934 (2)	0.04219 (10)
O1	−0.0186 (6)	0.1908 (3)	0.7336 (3)	0.1081 (18)
O2	0.1325 (5)	0.0950 (5)	0.7918 (3)	0.1118 (18)
O3	−0.2935 (6)	0.1625 (4)	0.7678 (3)	0.0960 (14)
H3	−0.2179	0.1873	0.7431	0.115*
C1	0.0072 (8)	0.1196 (5)	0.7824 (4)	0.081 (2)
C2	−0.1228 (5)	0.0620 (4)	0.8296 (3)	0.0522 (11)
C3	−0.2629 (6)	0.0880 (4)	0.8216 (3)	0.0570 (12)
C4	−0.3779 (6)	0.0353 (5)	0.8688 (4)	0.0689 (14)
H4	−0.4730	0.0519	0.8634	0.083*
C5	−0.3499 (6)	−0.0414 (5)	0.9234 (4)	0.0707 (14)
H5	−0.4266	−0.0764	0.9554	0.085*
C6	−0.2113 (7)	−0.0672 (5)	0.9316 (4)	0.0716 (14)
H6	−0.1937	−0.1193	0.9690	0.086*
C7	−0.0989 (6)	−0.0162 (4)	0.8848 (3)	0.0617 (12)
H7	−0.0046	−0.0344	0.8900	0.074*
O11	0.1346 (4)	0.4193 (2)	0.7177 (2)	0.0562 (8)
O12	0.2733 (5)	0.5535 (3)	0.6553 (2)	0.0748 (11)
O13	0.0194 (4)	0.4604 (3)	0.8654 (2)	0.0648 (9)
H13	0.0384	0.4223	0.8193	0.078*
C11	0.1982 (5)	0.5224 (3)	0.7164 (3)	0.0442 (9)
C12	0.1700 (4)	0.6045 (3)	0.7947 (3)	0.0407 (8)
C13	0.0823 (5)	0.5701 (4)	0.8645 (3)	0.0467 (10)
C14	0.0580 (6)	0.6490 (5)	0.9356 (3)	0.0645 (13)
H14	−0.0014	0.6260	0.9817	0.077*
C15	0.1213 (7)	0.7609 (5)	0.9381 (3)	0.0740 (16)
H15	0.1056	0.8132	0.9863	0.089*
C16	0.2082 (6)	0.7965 (4)	0.8697 (4)	0.0696 (14)
H16	0.2503	0.8726	0.8715	0.083*
C17	0.2322 (6)	0.7187 (4)	0.7989 (3)	0.0558 (11)
H17	0.2911	0.7428	0.7530	0.067*
N21	0.2855 (4)	0.0894 (3)	0.6089 (3)	0.0526 (9)
C22	0.3627 (6)	0.0235 (5)	0.6465 (4)	0.0751 (15)
H22	0.3981	0.0448	0.7071	0.090*
C23	0.3936 (7)	−0.0744 (5)	0.6013 (6)	0.090 (2)
H23	0.4506	−0.1174	0.6294	0.108*
C24	0.3379 (8)	−0.1058 (5)	0.5145 (6)	0.098 (2)
H24	0.3548	−0.1727	0.4824	0.118*
C27	−0.0004 (7)	0.1813 (6)	0.3642 (4)	0.0818 (17)
H27	−0.0448	0.1652	0.3053	0.098*
C28	−0.0146 (6)	0.2783 (5)	0.4192 (4)	0.0712 (15)
H28	−0.0696	0.3282	0.3991	0.085*
C29	0.0553 (6)	0.2984 (4)	0.5045 (3)	0.0605 (12)
H29	0.0483	0.3645	0.5419	0.073*
N30	0.1333 (4)	0.2278 (3)	0.5370 (2)	0.0472 (8)
C31	0.1458 (5)	0.1334 (4)	0.4834 (3)	0.0496 (10)
C26	0.0791 (6)	0.1089 (5)	0.3964 (3)	0.0727 (15)
H26	0.0884	0.0430	0.3596	0.087*
C25	0.2571 (7)	−0.0412 (4)	0.4727 (4)	0.0771 (16)
H25	0.2196	−0.0629	0.4126	0.092*
C32	0.2323 (5)	0.0582 (4)	0.5224 (3)	0.0512 (10)
N41	0.4715 (4)	0.3495 (3)	0.6612 (2)	0.0459 (8)
C42	0.5095 (5)	0.3697 (4)	0.5786 (3)	0.0547 (11)
H42	0.4367	0.3481	0.5306	0.066*
C43	0.6514 (6)	0.4210 (4)	0.5607 (4)	0.0664 (13)
H43	0.6740	0.4356	0.5025	0.080*
C44	0.7574 (6)	0.4497 (5)	0.6315 (4)	0.0779 (16)
H44	0.8550	0.4831	0.6219	0.094*
C47	0.5660 (7)	0.3693 (5)	0.9829 (4)	0.0762 (16)
H47	0.6298	0.3856	1.0353	0.091*
C48	0.4174 (7)	0.3288 (5)	0.9872 (3)	0.0740 (16)
H48	0.3772	0.3186	1.0427	0.089*
C49	0.3281 (7)	0.3034 (5)	0.9085 (3)	0.0741 (16)
H49	0.2265	0.2752	0.9118	0.089*
N50	0.3790 (4)	0.3170 (3)	0.8270 (2)	0.0545 (9)
C51	0.5237 (5)	0.3598 (4)	0.8221 (3)	0.0482 (10)
C46	0.6214 (6)	0.3861 (5)	0.8992 (3)	0.0665 (13)
H46	0.7227	0.4146	0.8949	0.080*
C45	0.7201 (5)	0.4292 (5)	0.7171 (4)	0.0704 (14)
H45	0.7922	0.4481	0.7655	0.084*
C52	0.5742 (4)	0.3801 (3)	0.7306 (3)	0.0447 (9)
O61	0.5469 (6)	0.7016 (4)	0.6474 (3)	0.1025 (14)
H61	0.4652	0.6606	0.6503	0.123*
C62	0.6266 (9)	0.7191 (6)	0.7309 (5)	0.110 (2)
H62A	0.6469	0.7982	0.7543	0.165*
H62B	0.7195	0.6937	0.7239	0.165*
H62C	0.5689	0.6777	0.7724	0.165*

	U11	U22	U33	U12	U13	U23
Cd1	0.04206 (16)	0.04538 (17)	0.03578 (14)	0.00416 (11)	−0.00069 (11)	0.00118 (11)
O1	0.169 (5)	0.061 (2)	0.080 (3)	−0.021 (3)	0.061 (3)	0.007 (2)
O2	0.071 (3)	0.145 (5)	0.090 (3)	−0.034 (3)	0.022 (3)	−0.014 (3)
O3	0.140 (4)	0.085 (3)	0.078 (3)	0.044 (3)	0.019 (3)	0.031 (2)
C1	0.095 (5)	0.069 (4)	0.054 (3)	−0.033 (3)	0.029 (3)	−0.022 (3)
C2	0.061 (3)	0.045 (2)	0.039 (2)	−0.011 (2)	0.014 (2)	−0.0069 (18)
C3	0.081 (3)	0.044 (2)	0.044 (2)	0.011 (2)	0.006 (2)	−0.0001 (19)
C4	0.055 (3)	0.085 (4)	0.065 (3)	0.013 (3)	0.010 (2)	0.006 (3)
C5	0.064 (3)	0.081 (4)	0.062 (3)	−0.003 (3)	0.021 (3)	0.015 (3)
C6	0.082 (4)	0.068 (3)	0.064 (3)	0.008 (3)	0.004 (3)	0.019 (3)
C7	0.058 (3)	0.067 (3)	0.056 (3)	0.007 (2)	0.000 (2)	0.002 (2)
O11	0.0567 (19)	0.0455 (17)	0.0627 (19)	0.0080 (14)	0.0092 (15)	−0.0037 (14)
O12	0.111 (3)	0.062 (2)	0.052 (2)	0.015 (2)	0.034 (2)	0.0050 (16)
O13	0.061 (2)	0.069 (2)	0.061 (2)	0.0034 (17)	0.0169 (16)	0.0076 (17)
C11	0.052 (2)	0.043 (2)	0.037 (2)	0.0111 (18)	−0.0021 (18)	0.0018 (17)
C12	0.044 (2)	0.042 (2)	0.0356 (19)	0.0112 (17)	−0.0067 (16)	0.0019 (16)
C13	0.040 (2)	0.058 (3)	0.042 (2)	0.0124 (19)	−0.0037 (17)	0.0044 (19)
C14	0.068 (3)	0.086 (4)	0.042 (2)	0.028 (3)	0.009 (2)	−0.001 (2)
C15	0.096 (4)	0.080 (4)	0.048 (3)	0.041 (3)	−0.003 (3)	−0.016 (3)
C16	0.076 (4)	0.050 (3)	0.076 (3)	0.012 (2)	−0.006 (3)	−0.012 (2)
C17	0.066 (3)	0.048 (3)	0.053 (3)	0.013 (2)	0.004 (2)	0.004 (2)
N21	0.052 (2)	0.048 (2)	0.059 (2)	0.0140 (17)	0.0044 (18)	0.0080 (17)
C22	0.067 (3)	0.071 (4)	0.094 (4)	0.019 (3)	0.012 (3)	0.027 (3)
C23	0.073 (4)	0.065 (4)	0.148 (7)	0.029 (3)	0.028 (4)	0.041 (4)
C24	0.090 (5)	0.055 (3)	0.154 (7)	0.026 (3)	0.048 (5)	0.001 (4)
C27	0.080 (4)	0.109 (5)	0.047 (3)	0.007 (4)	−0.018 (3)	0.001 (3)
C28	0.067 (3)	0.087 (4)	0.059 (3)	0.007 (3)	−0.012 (3)	0.024 (3)
C29	0.065 (3)	0.064 (3)	0.052 (3)	0.016 (2)	−0.009 (2)	0.006 (2)
N30	0.048 (2)	0.049 (2)	0.0397 (18)	0.0045 (16)	−0.0023 (15)	−0.0026 (15)
C31	0.047 (2)	0.051 (2)	0.042 (2)	−0.0027 (19)	0.0040 (18)	−0.0054 (18)
C26	0.080 (4)	0.079 (4)	0.044 (3)	0.000 (3)	−0.008 (2)	−0.017 (2)
C25	0.083 (4)	0.055 (3)	0.086 (4)	0.011 (3)	0.022 (3)	−0.015 (3)
C32	0.045 (2)	0.045 (2)	0.059 (3)	0.0016 (18)	0.009 (2)	−0.003 (2)
N41	0.0443 (19)	0.048 (2)	0.0446 (19)	0.0089 (15)	0.0057 (15)	0.0040 (15)
C42	0.057 (3)	0.061 (3)	0.047 (2)	0.010 (2)	0.008 (2)	0.008 (2)
C43	0.070 (3)	0.065 (3)	0.068 (3)	0.015 (3)	0.021 (3)	0.018 (3)
C44	0.053 (3)	0.092 (4)	0.091 (4)	0.006 (3)	0.021 (3)	0.027 (3)
C47	0.081 (4)	0.089 (4)	0.052 (3)	0.011 (3)	−0.028 (3)	0.003 (3)
C48	0.100 (4)	0.075 (4)	0.041 (3)	0.000 (3)	−0.007 (3)	0.015 (2)
C49	0.078 (4)	0.086 (4)	0.044 (3)	−0.022 (3)	−0.001 (2)	0.013 (3)
N50	0.057 (2)	0.060 (2)	0.0382 (18)	−0.0092 (18)	−0.0053 (16)	0.0098 (17)
C51	0.046 (2)	0.045 (2)	0.051 (2)	0.0090 (18)	−0.0109 (19)	0.0029 (19)
C46	0.056 (3)	0.084 (4)	0.054 (3)	0.012 (3)	−0.013 (2)	−0.001 (3)
C45	0.041 (3)	0.086 (4)	0.079 (4)	−0.005 (2)	−0.005 (2)	0.021 (3)
C52	0.037 (2)	0.044 (2)	0.053 (2)	0.0092 (17)	0.0001 (18)	0.0048 (18)
O61	0.115 (4)	0.105 (4)	0.080 (3)	−0.002 (3)	0.014 (3)	0.020 (3)
C62	0.102 (5)	0.113 (6)	0.110 (6)	0.021 (5)	0.004 (5)	0.001 (5)

Cd1—O11	2.305 (3)	C23—H23	0.9300
Cd1—N30	2.352 (3)	C24—C25	1.365 (9)
Cd1—N50	2.368 (4)	C24—H24	0.9300
Cd1—N41	2.369 (4)	C27—C26	1.365 (8)
Cd1—N21	2.377 (4)	C27—C28	1.375 (8)
Cd1—O1	2.391 (5)	C27—H27	0.9300
Cd1—O2	2.685 (5)	C28—C29	1.368 (7)
O1—C1	1.253 (8)	C28—H28	0.9300
O2—C1	1.242 (8)	C29—N30	1.340 (6)
O3—C3	1.348 (6)	C29—H29	0.9300
O3—H3	0.8200	N30—C31	1.336 (5)
C1—C2	1.507 (7)	C31—C26	1.378 (6)
C2—C3	1.377 (7)	C31—C32	1.476 (6)
C2—C7	1.380 (7)	C26—H26	0.9300
C3—C4	1.389 (7)	C25—C32	1.394 (6)
C4—C5	1.369 (7)	C25—H25	0.9300
C4—H4	0.9300	N41—C52	1.330 (5)
C5—C6	1.364 (8)	N41—C42	1.333 (5)
C5—H5	0.9300	C42—C43	1.378 (7)
C6—C7	1.360 (7)	C42—H42	0.9300
C6—H6	0.9300	C43—C44	1.363 (8)
C7—H7	0.9300	C43—H43	0.9300
O11—C11	1.283 (5)	C44—C45	1.374 (8)
O12—C11	1.217 (5)	C44—H44	0.9300
O13—C13	1.353 (5)	C47—C48	1.358 (8)
O13—H13	0.8200	C47—C46	1.388 (7)
C11—C12	1.497 (5)	C47—H47	0.9300
C12—C17	1.391 (6)	C48—C49	1.364 (7)
C12—C13	1.395 (6)	C48—H48	0.9300
C13—C14	1.387 (6)	C49—N50	1.335 (6)
C14—C15	1.371 (8)	C49—H49	0.9300
C14—H14	0.9300	N50—C51	1.332 (6)
C15—C16	1.379 (8)	C51—C46	1.387 (6)
C15—H15	0.9300	C51—C52	1.492 (6)
C16—C17	1.375 (6)	C46—H46	0.9300
C16—H16	0.9300	C45—C52	1.384 (6)
C17—H17	0.9300	C45—H45	0.9300
N21—C22	1.326 (6)	O61—C62	1.384 (8)
N21—C32	1.337 (6)	O61—H61	0.8200
C22—C23	1.374 (8)	C62—H62A	0.9600
C22—H22	0.9300	C62—H62B	0.9600
C23—C24	1.347 (10)	C62—H62C	0.9600
O11—Cd1—N30	90.83 (12)	C24—C23—C22	117.4 (6)
O11—Cd1—N50	87.64 (13)	C24—C23—H23	121.3
N30—Cd1—N50	164.41 (12)	C22—C23—H23	121.3
O11—Cd1—N41	95.01 (12)	C23—C24—C25	121.1 (6)
N30—Cd1—N41	95.40 (12)	C23—C24—H24	119.5
N50—Cd1—N41	69.31 (12)	C25—C24—H24	119.5
O11—Cd1—N21	159.80 (13)	C26—C27—C28	119.7 (5)
N30—Cd1—N21	68.98 (13)	C26—C27—H27	120.2
N50—Cd1—N21	111.80 (14)	C28—C27—H27	120.2
N41—Cd1—N21	87.26 (13)	C29—C28—C27	117.5 (5)
O11—Cd1—O1	76.61 (14)	C29—C28—H28	121.2
N30—Cd1—O1	89.34 (15)	C27—C28—H28	121.2
N50—Cd1—O1	105.36 (15)	N30—C29—C28	123.3 (5)
N41—Cd1—O1	170.46 (12)	N30—C29—H29	118.4
N21—Cd1—O1	102.18 (14)	C28—C29—H29	118.4
O11—Cd1—O2	116.15 (14)	C31—N30—C29	118.9 (4)
N30—Cd1—O2	117.82 (13)	C31—N30—Cd1	119.0 (3)
N50—Cd1—O2	76.51 (13)	C29—N30—Cd1	121.8 (3)
N41—Cd1—O2	132.29 (14)	N30—C31—C26	120.6 (5)
N21—Cd1—O2	75.45 (14)	N30—C31—C32	116.8 (4)
O1—Cd1—O2	50.73 (17)	C26—C31—C32	122.6 (4)
C1—O1—Cd1	100.0 (5)	C27—C26—C31	120.1 (5)
C1—O2—Cd1	86.3 (4)	C27—C26—H26	120.0
C3—O3—H3	109.5	C31—C26—H26	120.0
O2—C1—O1	122.8 (6)	C24—C25—C32	118.4 (6)
O2—C1—C2	120.3 (7)	C24—C25—H25	120.8
O1—C1—C2	116.9 (7)	C32—C25—H25	120.8
C3—C2—C7	119.3 (4)	N21—C32—C25	120.9 (5)
C3—C2—C1	121.9 (5)	N21—C32—C31	116.6 (4)
C7—C2—C1	118.7 (5)	C25—C32—C31	122.4 (5)
O3—C3—C2	122.0 (5)	C52—N41—C42	119.2 (4)
O3—C3—C4	118.2 (5)	C52—N41—Cd1	118.3 (3)
C2—C3—C4	119.8 (5)	C42—N41—Cd1	122.5 (3)
C5—C4—C3	119.3 (5)	N41—C42—C43	123.2 (5)
C5—C4—H4	120.3	N41—C42—H42	118.4
C3—C4—H4	120.3	C43—C42—H42	118.4
C6—C5—C4	121.0 (5)	C44—C43—C42	117.5 (5)
C6—C5—H5	119.5	C44—C43—H43	121.2
C4—C5—H5	119.5	C42—C43—H43	121.2
C7—C6—C5	119.6 (5)	C43—C44—C45	120.0 (5)
C7—C6—H6	120.2	C43—C44—H44	120.0
C5—C6—H6	120.2	C45—C44—H44	120.0
C6—C7—C2	120.9 (5)	C48—C47—C46	119.1 (5)
C6—C7—H7	119.5	C48—C47—H47	120.4
C2—C7—H7	119.5	C46—C47—H47	120.4
C11—O11—Cd1	130.0 (3)	C47—C48—C49	118.6 (5)
C13—O13—H13	109.5	C47—C48—H48	120.7
O12—C11—O11	123.5 (4)	C49—C48—H48	120.7
O12—C11—C12	121.3 (4)	N50—C49—C48	123.5 (5)
O11—C11—C12	115.2 (4)	N50—C49—H49	118.3
C17—C12—C13	118.5 (4)	C48—C49—H49	118.3
C17—C12—C11	119.7 (4)	C51—N50—C49	118.5 (4)
C13—C12—C11	121.9 (4)	C51—N50—Cd1	118.1 (3)
O13—C13—C14	118.1 (4)	C49—N50—Cd1	123.3 (3)
O13—C13—C12	121.7 (4)	N50—C51—C46	121.1 (4)
C14—C13—C12	120.1 (4)	N50—C51—C52	116.9 (4)
C15—C14—C13	120.0 (5)	C46—C51—C52	122.0 (4)
C15—C14—H14	120.0	C47—C46—C51	119.1 (5)
C13—C14—H14	120.0	C47—C46—H46	120.5
C14—C15—C16	120.7 (4)	C51—C46—H46	120.5
C14—C15—H15	119.7	C44—C45—C52	119.4 (5)
C16—C15—H15	119.7	C44—C45—H45	120.3
C17—C16—C15	119.5 (5)	C52—C45—H45	120.3
C17—C16—H16	120.3	N41—C52—C45	120.7 (4)
C15—C16—H16	120.3	N41—C52—C51	116.8 (4)
C16—C17—C12	121.2 (5)	C45—C52—C51	122.5 (4)
C16—C17—H17	119.4	C62—O61—H61	109.5
C12—C17—H17	119.4	O61—C62—H62A	109.5
C22—N21—C32	118.4 (4)	O61—C62—H62B	109.5
C22—N21—Cd1	123.3 (4)	H62A—C62—H62B	109.5
C32—N21—Cd1	118.3 (3)	O61—C62—H62C	109.5
N21—C22—C23	123.7 (6)	H62A—C62—H62C	109.5
N21—C22—H22	118.1	H62B—C62—H62C	109.5
C23—C22—H22	118.1
O2—C1—C2—C3	179.3 (5)	Cd1—O12—C11—C12	158.7 (5)
O1—C1—C2—C3	−1.5 (7)	Cd1—O11—C11—C12	−135.3 (3)
O2—C1—C2—C7	1.5 (7)	C11—C12—C13—O13	0.7 (6)
O1—C1—C2—C7	−179.4 (4)	Cd1—N30—C29—C28	−173.1 (4)
Cd1—O2—C1—C2	−177.0 (4)	Cd1—N30—C31—C32	−5.6 (5)
Cd1—O1—C1—C2	176.4 (3)	Cd1—N30—C31—C26	173.9 (4)
C1—C2—C3—O3	3.1 (7)	Cd1—N21—C22—C23	178.6 (4)
O12—C11—C12—C13	179.0 (4)	Cd1—N21—C32—C31	1.9 (5)
O11—C11—C12—C13	0.9 (6)	Cd1—N50—C51—C52	8.0 (5)
O12—C11—C12—C17	−1.0 (6)	Cd1—N21—C32—C25	−177.6 (4)
O11—C11—C12—C17	−179.1 (4)

Cg1 and Cg2 are the centroids of the C2–C7 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	1.82	2.545 (7)	147
O13—H13···O11	0.82	1.78	2.505 (4)	147
O61—H61···O12	0.82	1.98	2.802 (6)	177
C23—H23···O61i	0.93	2.57	3.429 (8)	154
C43—H43···O12ii	0.93	2.43	3.356 (6)	172
C45—H45···O13iii	0.93	2.47	3.370 (6)	163
C15—H15···Cg1iv	0.93	2.81	3.620 (6)	147
C47—H47···Cg2v	0.93	2.79	3.589 (6)	145
C62—H62A···Cg1vi	0.96	2.94	3.858 (8)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.82	1.82	2.545 (7)	147
O13—H13⋯O11	0.82	1.78	2.505 (4)	147
O61—H61⋯O12	0.82	1.98	2.802 (6)	177
C23—H23⋯O61i	0.93	2.57	3.429 (8)	154
C43—H43⋯O12ii	0.93	2.43	3.356 (6)	172
C45—H45⋯O13iii	0.93	2.47	3.370 (6)	163
C15—H15⋯Cg1iv	0.93	2.81	3.620 (6)	147
C47—H47⋯Cg2v	0.93	2.79	3.589 (6)	145
C62—H62A⋯Cg1vi	0.96	2.94	3.858 (8)	160

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 and Cg2 are the centroids of the C2–C7 and C12–C17 rings, respectively.