Aqua-bis(4-nitro-benzoato)-κO,O';κO-(piperidinium-4-carboxyl-ato-κO,O')cadmium(II).

In the mixed ligand title compound, [Cd(C(6)H(11)NO(2))(C(7)H(4)NO(4))(2)(H(2)O)], which exhibits a discrete mononuclear structure, the Cd(II )atom is in a distorted octa-hedral geometry, surrounded by five carboxyl-ate O atoms and one coordinated water mol-ecule. The piperdinium ring adopts a chair conformation and the two 4-nitro-benzoate rings are oriented at a dihedral angle of 75.8 (1)°. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mononuclear entities into a three-dimensional supra-molecular network.

Related literature

For the framework topologies and potential applications of coordination complexes with mixed ligands, see: Muthu et al. (2002 ▶); Fujita et al. (1994 ▶); Zheng et al. (2004 ▶); Rosi et al. (2003 ▶). For 4-piperidine­carboxylic acid as a zwitterion in aqueous solution, see: Mora et al. (2002 ▶); and for its ability to act selectively as a bridging or terminal ligand, see: Inomata et al. (2002 ▶). For related structures, see: Adams et al. (2006a ▶,b ▶); Podesta & Orpen (2002 ▶); Delgado et al. (2001 ▶). For Cd—O bond lengths, see: Inomata et al. (2004 ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

[Cd(C6H11NO2)(C7H4NO4)2(H2O)]

M = 591.80

Monoclinic,

a = 22.7135 (7) Å

b = 6.6294 (2) Å

c = 14.9658 (5) Å

β = 91.3400 (10)°

V = 2252.89 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.04 mm−1

T = 296 K

0.32 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.733, T max = 0.804

10944 measured reflections

3950 independent reflections

3615 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.056

S = 1.05

3950 reflections

316 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901811X/bq2139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901811X/bq2139Isup2.hkl

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

[Cd(C6H11NO2)(C7H4NO4)2(H2O)]	F(000) = 1192
Mr = 591.80	Dx = 1.745 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8249 reflections
a = 22.7135 (7) Å	θ = 2.9–27.8°
b = 6.6294 (2) Å	µ = 1.04 mm−1
c = 14.9658 (5) Å	T = 296 K
β = 91.340 (1)°	Block, pale-yellow
V = 2252.89 (12) Å3	0.32 × 0.28 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3950 independent reflections
Radiation source: fine-focus sealed tube	3615 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→26
Tmin = 0.733, Tmax = 0.804	k = −7→7
10944 measured reflections	l = −17→17

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) = 0.056	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0248P)2 + 1.8541P] where P = (Fo2 + 2Fc2)/3
3950 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.37 e Å−3
18 restraints	Δρmin = −0.32 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	0.219460 (8)	0.68670 (3)	0.490995 (11)	0.03129 (7)
O1	0.11917 (8)	0.7419 (3)	0.45149 (12)	0.0458 (5)
O2	0.18499 (8)	0.7480 (3)	0.34618 (12)	0.0372 (4)
O3	−0.10379 (9)	0.7684 (4)	0.13243 (15)	0.0595 (6)
O4	−0.04142 (11)	0.7829 (5)	0.02901 (15)	0.0822 (9)
O5	0.30087 (8)	0.5260 (3)	0.46044 (13)	0.0450 (5)
O6	0.34464 (10)	0.7998 (3)	0.40672 (16)	0.0563 (6)
O7	0.59387 (12)	0.2162 (5)	0.3509 (3)	0.1201 (13)
O8	0.54181 (11)	−0.0455 (4)	0.3661 (2)	0.0759 (7)
O9	0.24780 (8)	0.7579 (3)	0.63847 (11)	0.0371 (4)
O10	0.23667 (10)	1.0130 (3)	0.54773 (12)	0.0506 (5)
O11	0.18002 (9)	0.3782 (3)	0.52820 (14)	0.0490 (5)
H11A	0.1486	0.3692	0.4963	0.073*
H11B	0.2007	0.2720	0.5342	0.073*
N1	−0.05315 (11)	0.7738 (4)	0.10707 (16)	0.0432 (6)
N2	0.54786 (12)	0.1355 (4)	0.3662 (2)	0.0637 (8)
N3	0.28125 (9)	1.4822 (3)	0.78005 (14)	0.0354 (5)
H3A	0.2604	1.5610	0.7420	0.043*
H3B	0.2946	1.5603	0.8253	0.043*
C1	0.08383 (11)	0.7676 (4)	0.30125 (16)	0.0297 (5)
C2	0.02551 (11)	0.7688 (4)	0.32711 (17)	0.0326 (5)
H2	0.0169	0.7675	0.3875	0.039*
C3	−0.01979 (11)	0.7717 (4)	0.26380 (17)	0.0342 (6)
H3	−0.0589	0.7730	0.2806	0.041*
C4	−0.00508 (11)	0.7727 (4)	0.17489 (17)	0.0331 (6)
C5	0.05237 (12)	0.7745 (4)	0.14668 (17)	0.0384 (6)
H5	0.0608	0.7779	0.0862	0.046*
C6	0.09691 (11)	0.7712 (4)	0.21095 (17)	0.0354 (6)
H6	0.1360	0.7713	0.1937	0.043*
C7	0.13244 (11)	0.7537 (4)	0.37115 (17)	0.0309 (5)
C8	0.39914 (11)	0.4942 (4)	0.41654 (17)	0.0356 (6)
C9	0.44834 (14)	0.5789 (5)	0.3783 (2)	0.0549 (8)
H9	0.4480	0.7144	0.3623	0.066*
C10	0.49774 (14)	0.4642 (5)	0.3638 (3)	0.0622 (9)
H10	0.5312	0.5217	0.3398	0.075*
C11	0.49655 (12)	0.2628 (5)	0.3857 (2)	0.0445 (7)
C12	0.44856 (12)	0.1744 (4)	0.42363 (18)	0.0402 (6)
H12	0.4488	0.0377	0.4377	0.048*
C13	0.39998 (12)	0.2921 (4)	0.44039 (17)	0.0367 (6)
H13	0.3676	0.2356	0.4679	0.044*
C14	0.34426 (12)	0.6197 (4)	0.42904 (17)	0.0372 (6)
C15	0.27278 (11)	1.0862 (4)	0.69599 (15)	0.0306 (5)
H15	0.2954	1.0078	0.7404	0.037*
C16	0.31251 (11)	1.2505 (4)	0.66016 (17)	0.0349 (6)
H16A	0.3469	1.1889	0.6342	0.042*
H16B	0.2915	1.3242	0.6133	0.042*
C17	0.33216 (12)	1.3960 (4)	0.73289 (18)	0.0399 (6)
H17A	0.3577	1.3262	0.7756	0.048*
H17B	0.3546	1.5045	0.7067	0.048*
C18	0.24177 (13)	1.3237 (4)	0.81621 (17)	0.0370 (6)
H18A	0.2081	1.3870	0.8434	0.044*
H18B	0.2629	1.2472	0.8620	0.044*
C19	0.22071 (11)	1.1830 (4)	0.74276 (17)	0.0341 (6)
H19A	0.1969	1.2576	0.6994	0.041*
H19B	0.1963	1.0783	0.7679	0.041*
C20	0.25127 (11)	0.9437 (4)	0.62321 (16)	0.0326 (5)

	U11	U22	U33	U12	U13	U23
Cd1	0.03884 (12)	0.02632 (11)	0.02842 (11)	0.00414 (8)	−0.00520 (7)	−0.00244 (7)
O1	0.0443 (11)	0.0636 (13)	0.0294 (10)	0.0109 (10)	−0.0012 (8)	0.0033 (9)
O2	0.0321 (10)	0.0429 (10)	0.0364 (10)	0.0004 (8)	−0.0041 (8)	0.0006 (8)
O3	0.0341 (12)	0.0792 (16)	0.0646 (14)	0.0025 (11)	−0.0104 (10)	0.0013 (12)
O4	0.0595 (15)	0.149 (3)	0.0372 (13)	0.0001 (16)	−0.0105 (11)	0.0044 (15)
O5	0.0403 (11)	0.0396 (11)	0.0552 (12)	0.0066 (9)	0.0049 (9)	−0.0040 (9)
O6	0.0592 (13)	0.0369 (12)	0.0725 (15)	0.0100 (10)	−0.0061 (11)	0.0148 (10)
O7	0.0492 (15)	0.0736 (19)	0.240 (4)	0.0041 (14)	0.053 (2)	0.026 (2)
O8	0.0572 (14)	0.0516 (15)	0.120 (2)	0.0142 (12)	0.0266 (14)	0.0137 (14)
O9	0.0543 (11)	0.0239 (9)	0.0331 (9)	−0.0009 (8)	−0.0006 (8)	−0.0017 (7)
O10	0.0843 (14)	0.0275 (9)	0.0388 (10)	0.0071 (9)	−0.0225 (10)	−0.0030 (8)
O11	0.0479 (11)	0.0328 (10)	0.0650 (13)	−0.0032 (9)	−0.0228 (10)	0.0083 (9)
N1	0.0420 (14)	0.0409 (13)	0.0462 (15)	0.0022 (11)	−0.0101 (11)	0.0018 (11)
N2	0.0408 (14)	0.0533 (16)	0.098 (2)	0.0069 (12)	0.0211 (14)	0.0190 (15)
N3	0.0487 (13)	0.0225 (10)	0.0348 (11)	−0.0030 (9)	−0.0047 (9)	−0.0030 (9)
C1	0.0331 (13)	0.0233 (12)	0.0325 (13)	0.0020 (10)	−0.0009 (10)	0.0021 (10)
C2	0.0384 (14)	0.0297 (13)	0.0299 (13)	0.0030 (11)	0.0027 (11)	0.0025 (10)
C3	0.0301 (13)	0.0307 (13)	0.0418 (14)	0.0015 (10)	0.0034 (11)	0.0024 (11)
C4	0.0350 (14)	0.0280 (13)	0.0359 (14)	0.0012 (10)	−0.0067 (11)	0.0015 (10)
C5	0.0400 (15)	0.0461 (16)	0.0290 (13)	0.0027 (12)	0.0021 (11)	0.0029 (12)
C6	0.0306 (13)	0.0420 (15)	0.0338 (13)	0.0004 (11)	0.0028 (11)	0.0013 (11)
C7	0.0365 (14)	0.0211 (12)	0.0348 (14)	0.0027 (10)	−0.0035 (11)	0.0000 (10)
C8	0.0371 (14)	0.0330 (14)	0.0364 (13)	0.0006 (11)	−0.0047 (11)	0.0007 (11)
C9	0.0538 (19)	0.0326 (16)	0.079 (2)	−0.0024 (14)	0.0086 (16)	0.0141 (15)
C10	0.0452 (18)	0.0460 (19)	0.096 (3)	−0.0031 (15)	0.0208 (17)	0.0118 (18)
C11	0.0355 (15)	0.0420 (16)	0.0563 (18)	0.0032 (12)	0.0044 (13)	0.0059 (14)
C12	0.0409 (15)	0.0327 (14)	0.0469 (16)	0.0016 (12)	0.0012 (12)	0.0075 (12)
C13	0.0357 (14)	0.0367 (15)	0.0376 (14)	−0.0008 (11)	0.0015 (11)	0.0052 (11)
C14	0.0428 (15)	0.0368 (15)	0.0316 (13)	0.0036 (12)	−0.0089 (11)	−0.0015 (11)
C15	0.0397 (14)	0.0226 (12)	0.0293 (12)	0.0040 (10)	−0.0045 (10)	0.0004 (10)
C16	0.0326 (13)	0.0373 (14)	0.0348 (13)	0.0010 (11)	0.0039 (11)	−0.0015 (11)
C17	0.0365 (14)	0.0382 (15)	0.0447 (15)	−0.0071 (12)	−0.0039 (12)	0.0011 (12)
C18	0.0517 (16)	0.0265 (13)	0.0332 (13)	−0.0015 (11)	0.0082 (12)	−0.0019 (10)
C19	0.0386 (14)	0.0273 (13)	0.0367 (14)	−0.0066 (11)	0.0064 (11)	−0.0020 (11)
C20	0.0410 (13)	0.0248 (12)	0.0318 (12)	0.0055 (10)	−0.0035 (10)	−0.0039 (10)

Cd1—O5	2.1917 (18)	C3—C4	1.379 (4)
Cd1—O11	2.3061 (19)	C3—H3	0.9300
Cd1—O2	2.3229 (17)	C4—C5	1.381 (4)
Cd1—O9	2.3327 (17)	C5—C6	1.380 (4)
Cd1—O10	2.3534 (18)	C5—H5	0.9300
Cd1—O1	2.3684 (19)	C6—H6	0.9300
Cd1—C7	2.675 (2)	C8—C9	1.386 (4)
Cd1—C20	2.697 (2)	C8—C13	1.387 (4)
O1—C7	1.249 (3)	C8—C14	1.514 (4)
O2—C7	1.260 (3)	C9—C10	1.377 (4)
O3—N1	1.220 (3)	C9—H9	0.9300
O4—N1	1.206 (3)	C10—C11	1.375 (4)
O5—C14	1.265 (3)	C10—H10	0.9300
O6—C14	1.240 (3)	C11—C12	1.372 (4)
O7—N2	1.201 (4)	C12—C13	1.379 (4)
O8—N2	1.207 (4)	C12—H12	0.9300
O9—C20	1.256 (3)	C13—H13	0.9300
O10—C20	1.257 (3)	C15—C20	1.514 (3)
O11—H11A	0.8504	C15—C16	1.520 (4)
O11—H11B	0.8500	C15—C19	1.529 (3)
N1—C4	1.473 (3)	C15—H15	0.9800
N2—C11	1.474 (4)	C16—C17	1.514 (4)
N3—C17	1.483 (3)	C16—H16A	0.9700
N3—C18	1.491 (3)	C16—H16B	0.9700
N3—H3A	0.9000	C17—H17A	0.9700
N3—H3B	0.9000	C17—H17B	0.9700
C1—C2	1.389 (4)	C18—C19	1.511 (3)
C1—C6	1.391 (3)	C18—H18A	0.9700
C1—C7	1.506 (3)	C18—H18B	0.9700
C2—C3	1.382 (4)	C19—H19A	0.9700
C2—H2	0.9300	C19—H19B	0.9700
O5—Cd1—O11	87.34 (7)	C1—C6—H6	119.7
O5—Cd1—O2	99.09 (7)	O1—C7—O2	122.4 (2)
O11—Cd1—O2	104.84 (7)	O1—C7—C1	118.9 (2)
O5—Cd1—O9	94.60 (7)	O2—C7—C1	118.7 (2)
O11—Cd1—O9	92.93 (7)	O1—C7—Cd1	62.30 (13)
O2—Cd1—O9	157.95 (7)	O2—C7—Cd1	60.23 (12)
O5—Cd1—O10	112.86 (8)	C1—C7—Cd1	173.83 (17)
O11—Cd1—O10	142.21 (7)	C9—C8—C13	119.4 (3)
O2—Cd1—O10	103.02 (6)	C9—C8—C14	120.2 (2)
O9—Cd1—O10	55.45 (6)	C13—C8—C14	120.4 (2)
O5—Cd1—O1	146.54 (7)	C10—C9—C8	120.6 (3)
O11—Cd1—O1	79.66 (7)	C10—C9—H9	119.7
O2—Cd1—O1	55.86 (6)	C8—C9—H9	119.7
O9—Cd1—O1	116.58 (6)	C11—C10—C9	118.6 (3)
O10—Cd1—O1	95.67 (7)	C11—C10—H10	120.7
O5—Cd1—C7	123.68 (7)	C9—C10—H10	120.7
O11—Cd1—C7	91.37 (7)	C12—C11—C10	122.3 (3)
O2—Cd1—C7	28.08 (7)	C12—C11—N2	118.4 (3)
O9—Cd1—C7	141.64 (7)	C10—C11—N2	119.3 (3)
O10—Cd1—C7	101.72 (7)	C11—C12—C13	118.7 (3)
O1—Cd1—C7	27.83 (7)	C11—C12—H12	120.7
O5—Cd1—C20	104.32 (7)	C13—C12—H12	120.7
O11—Cd1—C20	118.82 (7)	C12—C13—C8	120.4 (3)
O2—Cd1—C20	130.75 (7)	C12—C13—H13	119.8
O9—Cd1—C20	27.72 (7)	C8—C13—H13	119.8
O10—Cd1—C20	27.77 (7)	O6—C14—O5	125.7 (3)
O1—Cd1—C20	108.98 (7)	O6—C14—C8	119.0 (3)
C7—Cd1—C20	124.63 (7)	O5—C14—C8	115.3 (2)
C7—O1—Cd1	89.86 (15)	C20—C15—C16	112.2 (2)
C7—O2—Cd1	91.69 (15)	C20—C15—C19	110.6 (2)
C14—O5—Cd1	120.47 (17)	C16—C15—C19	109.4 (2)
C20—O9—Cd1	92.50 (14)	C20—C15—H15	108.2
C20—O10—Cd1	91.50 (15)	C16—C15—H15	108.2
Cd1—O11—H11A	104.6	C19—C15—H15	108.2
Cd1—O11—H11B	122.9	C17—C16—C15	111.8 (2)
H11A—O11—H11B	117.1	C17—C16—H16A	109.3
O4—N1—O3	122.3 (2)	C15—C16—H16A	109.3
O4—N1—C4	119.4 (2)	C17—C16—H16B	109.3
O3—N1—C4	118.3 (2)	C15—C16—H16B	109.3
O7—N2—O8	122.8 (3)	H16A—C16—H16B	107.9
O7—N2—C11	118.6 (3)	N3—C17—C16	111.6 (2)
O8—N2—C11	118.6 (3)	N3—C17—H17A	109.3
C17—N3—C18	112.6 (2)	C16—C17—H17A	109.3
C17—N3—H3A	109.1	N3—C17—H17B	109.3
C18—N3—H3A	109.1	C16—C17—H17B	109.3
C17—N3—H3B	109.1	H17A—C17—H17B	108.0
C18—N3—H3B	109.1	N3—C18—C19	110.7 (2)
H3A—N3—H3B	107.8	N3—C18—H18A	109.5
C2—C1—C6	119.8 (2)	C19—C18—H18A	109.5
C2—C1—C7	119.7 (2)	N3—C18—H18B	109.5
C6—C1—C7	120.4 (2)	C19—C18—H18B	109.5
C3—C2—C1	120.6 (2)	H18A—C18—H18B	108.1
C3—C2—H2	119.7	C18—C19—C15	110.9 (2)
C1—C2—H2	119.7	C18—C19—H19A	109.5
C4—C3—C2	117.9 (2)	C15—C19—H19A	109.5
C4—C3—H3	121.0	C18—C19—H19B	109.5
C2—C3—H3	121.0	C15—C19—H19B	109.5
C3—C4—C5	123.1 (2)	H19A—C19—H19B	108.0
C3—C4—N1	118.2 (2)	O9—C20—O10	120.4 (2)
C5—C4—N1	118.7 (2)	O9—C20—C15	120.1 (2)
C6—C5—C4	118.0 (2)	O10—C20—C15	119.5 (2)
C6—C5—H5	121.0	O9—C20—Cd1	59.78 (12)
C4—C5—H5	121.0	O10—C20—Cd1	60.73 (13)
C5—C6—C1	120.5 (2)	C15—C20—Cd1	176.71 (18)
C5—C6—H6	119.7
O5—Cd1—O1—C7	−44.7 (2)	C20—Cd1—C7—O2	113.00 (15)
O11—Cd1—O1—C7	−113.45 (16)	O5—Cd1—C7—C1	49.5 (17)
O2—Cd1—O1—C7	2.54 (14)	O11—Cd1—C7—C1	−38.2 (17)
O9—Cd1—O1—C7	158.45 (14)	O2—Cd1—C7—C1	81.7 (17)
O10—Cd1—O1—C7	104.44 (16)	O9—Cd1—C7—C1	−134.7 (17)
C20—Cd1—O1—C7	129.46 (15)	O10—Cd1—C7—C1	177.4 (17)
O5—Cd1—O2—C7	153.29 (15)	O1—Cd1—C7—C1	−102.8 (17)
O11—Cd1—O2—C7	63.65 (15)	C20—Cd1—C7—C1	−165.3 (17)
O9—Cd1—O2—C7	−79.0 (2)	C13—C8—C9—C10	0.1 (5)
O10—Cd1—O2—C7	−90.55 (15)	C14—C8—C9—C10	−177.8 (3)
O1—Cd1—O2—C7	−2.52 (14)	C8—C9—C10—C11	1.8 (5)
C20—Cd1—O2—C7	−88.77 (16)	C9—C10—C11—C12	−1.9 (5)
O11—Cd1—O5—C14	176.52 (19)	C9—C10—C11—N2	176.8 (3)
O2—Cd1—O5—C14	71.91 (19)	O7—N2—C11—C12	−164.7 (4)
O9—Cd1—O5—C14	−90.75 (19)	O8—N2—C11—C12	15.5 (5)
O10—Cd1—O5—C14	−36.4 (2)	O7—N2—C11—C10	16.6 (5)
O1—Cd1—O5—C14	109.9 (2)	O8—N2—C11—C10	−163.1 (4)
C7—Cd1—O5—C14	86.6 (2)	C10—C11—C12—C13	−0.1 (5)
C20—Cd1—O5—C14	−64.4 (2)	N2—C11—C12—C13	−178.8 (3)
O5—Cd1—O9—C20	112.35 (16)	C11—C12—C13—C8	2.1 (4)
O11—Cd1—O9—C20	−160.08 (16)	C9—C8—C13—C12	−2.1 (4)
O2—Cd1—O9—C20	−16.0 (3)	C14—C8—C13—C12	175.7 (2)
O10—Cd1—O9—C20	−2.34 (15)	Cd1—O5—C14—O6	−5.4 (4)
O1—Cd1—O9—C20	−80.19 (16)	Cd1—O5—C14—C8	176.17 (15)
C7—Cd1—O9—C20	−64.15 (19)	C9—C8—C14—O6	−1.8 (4)
O5—Cd1—O10—C20	−77.03 (17)	C13—C8—C14—O6	−179.6 (3)
O11—Cd1—O10—C20	40.4 (2)	C9—C8—C14—O5	176.7 (3)
O2—Cd1—O10—C20	177.09 (16)	C13—C8—C14—O5	−1.1 (4)
O9—Cd1—O10—C20	2.33 (15)	C20—C15—C16—C17	178.2 (2)
O1—Cd1—O10—C20	120.86 (16)	C19—C15—C16—C17	55.1 (3)
C7—Cd1—O10—C20	148.36 (16)	C18—N3—C17—C16	54.5 (3)
C6—C1—C2—C3	0.6 (4)	C15—C16—C17—N3	−54.3 (3)
C7—C1—C2—C3	−176.9 (2)	C17—N3—C18—C19	−56.0 (3)
C1—C2—C3—C4	0.2 (4)	N3—C18—C19—C15	57.1 (3)
C2—C3—C4—C5	−1.2 (4)	C20—C15—C19—C18	179.4 (2)
C2—C3—C4—N1	179.4 (2)	C16—C15—C19—C18	−56.6 (3)
O4—N1—C4—C3	177.0 (3)	Cd1—O9—C20—O10	4.2 (3)
O3—N1—C4—C3	−1.9 (4)	Cd1—O9—C20—C15	−176.2 (2)
O4—N1—C4—C5	−2.4 (4)	Cd1—O10—C20—O9	−4.1 (3)
O3—N1—C4—C5	178.7 (3)	Cd1—O10—C20—C15	176.2 (2)
C3—C4—C5—C6	1.3 (4)	C16—C15—C20—O9	140.5 (2)
N1—C4—C5—C6	−179.3 (2)	C19—C15—C20—O9	−97.1 (3)
C4—C5—C6—C1	−0.5 (4)	C16—C15—C20—O10	−39.9 (3)
C2—C1—C6—C5	−0.4 (4)	C19—C15—C20—O10	82.6 (3)
C7—C1—C6—C5	177.0 (2)	C16—C15—C20—Cd1	53 (3)
Cd1—O1—C7—O2	−4.6 (3)	C19—C15—C20—Cd1	175 (3)
Cd1—O1—C7—C1	173.1 (2)	O5—Cd1—C20—O9	−72.07 (16)
Cd1—O2—C7—O1	4.7 (3)	O11—Cd1—C20—O9	22.85 (18)
Cd1—O2—C7—C1	−173.03 (19)	O2—Cd1—C20—O9	172.13 (13)
C2—C1—C7—O1	0.5 (4)	O10—Cd1—C20—O9	175.9 (3)
C6—C1—C7—O1	−176.9 (2)	O1—Cd1—C20—O9	111.27 (15)
C2—C1—C7—O2	178.3 (2)	C7—Cd1—C20—O9	137.25 (15)
C6—C1—C7—O2	0.9 (4)	O5—Cd1—C20—O10	112.06 (16)
C2—C1—C7—Cd1	100.0 (17)	O11—Cd1—C20—O10	−153.02 (15)
C6—C1—C7—Cd1	−77.4 (17)	O2—Cd1—C20—O10	−3.7 (2)
O5—Cd1—C7—O1	152.24 (15)	O9—Cd1—C20—O10	−175.9 (3)
O11—Cd1—C7—O1	64.52 (16)	O1—Cd1—C20—O10	−64.60 (17)
O2—Cd1—C7—O1	−175.5 (2)	C7—Cd1—C20—O10	−38.62 (19)
O9—Cd1—C7—O1	−31.9 (2)	O5—Cd1—C20—C15	17 (3)
O10—Cd1—C7—O1	−79.80 (16)	O11—Cd1—C20—C15	112 (3)
C20—Cd1—C7—O1	−62.53 (18)	O2—Cd1—C20—C15	−99 (3)
O5—Cd1—C7—O2	−32.23 (17)	O9—Cd1—C20—C15	89 (3)
O11—Cd1—C7—O2	−119.95 (15)	O10—Cd1—C20—C15	−95 (3)
O9—Cd1—C7—O2	143.58 (14)	O1—Cd1—C20—C15	−159 (3)
O10—Cd1—C7—O2	95.73 (15)	C7—Cd1—C20—C15	−133 (3)
O1—Cd1—C7—O2	175.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11A···O3i	0.85	2.26	3.019 (3)	149
O11—H11B···O10ii	0.85	1.91	2.754 (3)	172
N3—H3A···O9iii	0.90	2.04	2.887 (3)	156
N3—H3B···O6iv	0.90	1.89	2.762 (3)	163

Table 1

Selected geometric parameters (Å, °)

Cd1—O5	2.1917 (18)
Cd1—O11	2.3061 (19)
Cd1—O2	2.3229 (17)
Cd1—O9	2.3327 (17)
Cd1—O10	2.3534 (18)
Cd1—O1	2.3684 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11A⋯O3i	0.85	2.26	3.019 (3)	149
O11—H11B⋯O10ii	0.85	1.91	2.754 (3)	172
N3—H3A⋯O9iii	0.90	2.04	2.887 (3)	156
N3—H3B⋯O6iv	0.90	1.89	2.762 (3)	163

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