catena-Poly[[aqua-bis-(3-chloro-benzoato-κ(2) O,O')cadmium]-μ-N,N-di-ethyl-nico-tin-amide-κ(2) N (1):O].

In the crystal of the title Cd(II) polymeric complex, [Cd(C7H4ClO2)2(C10H14N2O)(H2O)] n , the Cd(II) cation is chelated by two chloro-benzoate anions and coordinated by two N,N-di--ethyl-nicotinamide (DENA) ligands and one water mol-ecule in a distorted NO6 penta-gonal-bipyramidal geometry. The Cd(II) cations are bridged by the pyridine N atom and carbonyl O atom of the DENA ligand to form a polymeric chain running along the b axis. Inter-molecular O-H⋯O hydrogen bonds between coordinating water mol-ecules and carboxyl-ate groups link adjacent chains into layers parallel to the bc plane. π-π contacts between benzene rings [shortest centroid-centroid distance = 3.912 (2) Å] further stabilizes the crystal structure. In the mol-ecule, weak C-H⋯O hydrogen bonds occur between the pyridine ring and carboxyl-ate groups; the dihedral angles between the carboxyl-ate groups and adjacent benzene rings are 4.6 (3) and 12.8 (3)°, while the benzene rings are oriented at a dihedral angle of 1.89 (13)°.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-di­ethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Çaylak Delibaş et al. (2013 ▶); Greenaway et al. (1984 ▶); Hökelek et al. (1995 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶,e ▶,f ▶,g ▶); Hökelek et al. (2011 ▶); Necefoğlu et al. (2010a ▶,b ▶); Sertçelik et al. (2013 ▶).

Experimental

Crystal data

[Cd(C7H4ClO2)2(C10H14N2O)(H2O)]

M = 619.76

Monoclinic,

a = 25.1809 (5) Å

b = 7.0161 (3) Å

c = 30.6755 (6) Å

β = 106.203 (3)°

V = 5204.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.09 mm−1

T = 296 K

0.35 × 0.15 × 0.10 mm

Data collection

Bruker SMART BREEZE CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.823, T max = 0.897

100329 measured reflections

6531 independent reflections

6170 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.093

S = 1.35

6531 reflections

326 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −1.02 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301965X/xu5721sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301965X/xu5721Isup2.hkl

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

[Cd(C7H4ClO2)2(C10H14N2O)(H2O)]	F(000) = 2496
Mr = 619.76	Dx = 1.582 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 9713 reflections
a = 25.1809 (5) Å	θ = 2.5–28.4°
b = 7.0161 (3) Å	µ = 1.09 mm−1
c = 30.6755 (6) Å	T = 296 K
β = 106.203 (3)°	Rod-shaped, colourless
V = 5204.2 (3) Å3	0.35 × 0.15 × 0.10 mm
Z = 8

Bruker SMART BREEZE CCD diffractometer	6531 independent reflections
Radiation source: fine-focus sealed tube	6170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −33→33
Tmin = 0.823, Tmax = 0.897	k = −9→9
100329 measured reflections	l = −41→40

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	w = 1/[σ2(Fo2) + (0.0097P)2 + 22.0143P] where P = (Fo2 + 2Fc2)/3
6531 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.77 e Å−3
4 restraints	Δρmin = −1.02 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.430006 (10)	0.86384 (4)	0.032753 (9)	0.03649 (8)
Cl1	0.67865 (6)	0.6435 (2)	0.24132 (4)	0.0797 (4)
Cl2	0.20678 (5)	1.2006 (2)	−0.17853 (4)	0.0741 (4)
O1	0.50773 (11)	0.7328 (5)	0.09538 (10)	0.0534 (7)
O2	0.50591 (11)	1.0331 (5)	0.07578 (9)	0.0533 (7)
O3	0.35198 (12)	0.9354 (4)	−0.03179 (10)	0.0547 (8)
O4	0.41552 (11)	1.1524 (4)	−0.00840 (9)	0.0500 (7)
O5	0.39003 (12)	0.9782 (4)	0.09065 (10)	0.0498 (7)
O6	0.47410 (12)	0.7107 (5)	−0.01422 (11)	0.0485 (7)
H61	0.472 (2)	0.785 (7)	−0.0367 (12)	0.083 (19)*
H62	0.5081 (12)	0.709 (10)	0.0016 (18)	0.13 (3)*
N1	0.38036 (12)	0.6005 (4)	0.04343 (10)	0.0349 (6)
N2	0.42885 (14)	1.1630 (5)	0.15138 (11)	0.0453 (8)
C1	0.52769 (14)	0.8941 (6)	0.10063 (12)	0.0420 (9)
C2	0.57856 (13)	0.9332 (6)	0.13935 (12)	0.0368 (8)
C3	0.60309 (14)	0.7865 (6)	0.16792 (12)	0.0410 (8)
H3	0.5892	0.6631	0.1627	0.049*
C4	0.64831 (15)	0.8243 (6)	0.20430 (13)	0.0451 (9)
C5	0.66979 (17)	1.0049 (8)	0.21233 (15)	0.0575 (12)
H5	0.7004	1.0287	0.2369	0.069*
C6	0.6455 (2)	1.1492 (8)	0.18368 (16)	0.0648 (13)
H6	0.6597	1.2721	0.1888	0.078*
C7	0.59975 (17)	1.1136 (6)	0.14707 (15)	0.0516 (10)
H7	0.5835	1.2125	0.1278	0.062*
C8	0.37094 (14)	1.0967 (5)	−0.03489 (11)	0.0367 (8)
C9	0.33859 (14)	1.2296 (5)	−0.07074 (11)	0.0328 (7)
C10	0.29377 (14)	1.1625 (5)	−0.10465 (11)	0.0364 (7)
H10	0.2847	1.0337	−0.1060	0.044*
C11	0.26293 (16)	1.2868 (6)	−0.13623 (13)	0.0458 (9)
C12	0.2747 (2)	1.4770 (7)	−0.13478 (15)	0.0583 (12)
H12	0.2530	1.5599	−0.1561	0.070*
C13	0.3196 (2)	1.5445 (6)	−0.10090 (16)	0.0606 (12)
H13	0.3280	1.6737	−0.0994	0.073*
C14	0.35155 (18)	1.4214 (6)	−0.06956 (13)	0.0465 (9)
H14	0.3821	1.4673	−0.0474	0.056*
C15	0.40358 (14)	0.4560 (5)	0.07000 (12)	0.0363 (7)
H15	0.4418	0.4552	0.0822	0.044*
C16	0.37313 (15)	0.3070 (5)	0.08017 (12)	0.0346 (7)
C17	0.31657 (15)	0.3072 (6)	0.06121 (13)	0.0442 (9)
H17	0.2951	0.2065	0.0665	0.053*
C18	0.29234 (16)	0.4580 (7)	0.03445 (15)	0.0523 (10)
H18	0.2542	0.4629	0.0220	0.063*
C19	0.32558 (15)	0.6014 (6)	0.02650 (13)	0.0442 (9)
H19	0.3091	0.7037	0.0085	0.053*
C20	0.39878 (15)	1.1380 (5)	0.10824 (13)	0.0408 (8)
C21	0.43608 (18)	1.3440 (7)	0.17587 (14)	0.0530 (10)
H21A	0.4277	1.3260	0.2046	0.064*
H21B	0.4101	1.4362	0.1583	0.064*
C22	0.4944 (2)	1.4228 (8)	0.18486 (17)	0.0724 (14)
H22A	0.4972	1.5408	0.2012	0.109*
H22B	0.5026	1.4446	0.1565	0.109*
H22C	0.5203	1.3328	0.2026	0.109*
C23	0.4519 (2)	0.9923 (7)	0.17814 (16)	0.0606 (12)
H23A	0.4863	1.0261	0.2004	0.073*
H23B	0.4601	0.8969	0.1581	0.073*
C24	0.4129 (3)	0.9093 (9)	0.2021 (2)	0.097 (2)
H24A	0.4306	0.8052	0.2210	0.146*
H24B	0.3802	0.8641	0.1802	0.146*
H24C	0.4029	1.0056	0.2207	0.146*

	U11	U22	U33	U12	U13	U23
Cd1	0.03456 (13)	0.03444 (13)	0.03743 (13)	−0.00848 (11)	0.00502 (9)	0.00642 (11)
Cl1	0.0728 (8)	0.0926 (10)	0.0612 (7)	0.0290 (8)	−0.0022 (6)	0.0143 (7)
Cl2	0.0523 (6)	0.1018 (11)	0.0533 (6)	−0.0002 (7)	−0.0100 (5)	0.0020 (7)
O1	0.0415 (15)	0.0632 (19)	0.0483 (16)	−0.0173 (14)	0.0008 (12)	−0.0009 (14)
O2	0.0414 (15)	0.070 (2)	0.0435 (15)	−0.0062 (14)	0.0043 (12)	0.0154 (15)
O3	0.0528 (16)	0.0446 (16)	0.0570 (17)	−0.0091 (13)	−0.0005 (13)	0.0198 (14)
O4	0.0392 (14)	0.0561 (17)	0.0474 (15)	−0.0072 (13)	−0.0002 (11)	0.0094 (14)
O5	0.0609 (17)	0.0322 (14)	0.0653 (18)	−0.0061 (13)	0.0322 (15)	−0.0015 (13)
O6	0.0440 (16)	0.0526 (17)	0.0512 (17)	−0.0086 (13)	0.0173 (13)	0.0004 (14)
N1	0.0369 (14)	0.0292 (15)	0.0384 (15)	−0.0081 (12)	0.0103 (12)	0.0011 (12)
N2	0.0537 (19)	0.0402 (18)	0.0457 (18)	0.0070 (15)	0.0200 (15)	0.0106 (14)
C1	0.0291 (16)	0.063 (3)	0.0349 (18)	−0.0060 (17)	0.0107 (14)	0.0010 (18)
C2	0.0260 (15)	0.049 (2)	0.0356 (17)	−0.0057 (14)	0.0095 (13)	−0.0025 (15)
C3	0.0344 (17)	0.048 (2)	0.0401 (19)	−0.0016 (16)	0.0102 (15)	−0.0038 (17)
C4	0.0351 (18)	0.060 (3)	0.0383 (19)	0.0069 (17)	0.0074 (15)	−0.0016 (18)
C5	0.041 (2)	0.080 (3)	0.045 (2)	−0.013 (2)	0.0015 (18)	−0.014 (2)
C6	0.062 (3)	0.059 (3)	0.068 (3)	−0.023 (2)	0.008 (2)	−0.014 (2)
C7	0.049 (2)	0.046 (2)	0.058 (2)	−0.0066 (19)	0.0110 (19)	0.002 (2)
C8	0.0339 (17)	0.045 (2)	0.0324 (17)	−0.0001 (15)	0.0108 (13)	0.0058 (15)
C9	0.0377 (17)	0.0326 (17)	0.0300 (16)	−0.0011 (14)	0.0128 (13)	0.0032 (13)
C10	0.0373 (17)	0.0345 (18)	0.0376 (18)	−0.0006 (14)	0.0109 (14)	0.0006 (14)
C11	0.041 (2)	0.060 (3)	0.0341 (19)	0.0080 (18)	0.0072 (15)	0.0051 (18)
C12	0.070 (3)	0.053 (3)	0.048 (2)	0.018 (2)	0.011 (2)	0.018 (2)
C13	0.085 (3)	0.033 (2)	0.061 (3)	0.003 (2)	0.016 (2)	0.007 (2)
C14	0.059 (2)	0.037 (2)	0.040 (2)	−0.0086 (18)	0.0097 (17)	−0.0011 (16)
C15	0.0350 (17)	0.0350 (18)	0.0388 (18)	−0.0089 (14)	0.0102 (14)	0.0001 (15)
C16	0.0413 (18)	0.0294 (16)	0.0366 (17)	−0.0043 (14)	0.0168 (14)	−0.0004 (14)
C17	0.0406 (19)	0.041 (2)	0.054 (2)	−0.0147 (16)	0.0187 (17)	0.0038 (17)
C18	0.0332 (18)	0.060 (3)	0.061 (3)	−0.0097 (18)	0.0097 (17)	0.012 (2)
C19	0.0403 (19)	0.039 (2)	0.052 (2)	−0.0046 (16)	0.0100 (16)	0.0093 (17)
C20	0.0464 (19)	0.0345 (18)	0.049 (2)	−0.0065 (16)	0.0265 (17)	0.0047 (16)
C21	0.061 (3)	0.055 (3)	0.043 (2)	0.009 (2)	0.0142 (19)	0.0029 (19)
C22	0.070 (3)	0.079 (4)	0.062 (3)	−0.010 (3)	0.010 (2)	0.000 (3)
C23	0.069 (3)	0.056 (3)	0.065 (3)	0.022 (2)	0.032 (2)	0.024 (2)
C24	0.116 (5)	0.085 (4)	0.117 (5)	0.037 (4)	0.076 (4)	0.059 (4)

Cd1—O1	2.504 (3)	C9—C10	1.386 (5)
Cd1—O2	2.323 (3)	C9—C14	1.383 (5)
Cd1—O3	2.421 (3)	C10—C11	1.372 (5)
Cd1—O4	2.360 (3)	C10—H10	0.9300
Cd1—O5	2.410 (3)	C11—C12	1.365 (6)
Cd1—O6	2.314 (3)	C12—C13	1.388 (7)
Cd1—N1	2.305 (3)	C12—H12	0.9300
Cd1—C1	2.752 (4)	C13—H13	0.9300
Cd1—C8	2.732 (3)	C14—C13	1.373 (6)
Cl1—C4	1.732 (4)	C14—H14	0.9300
Cl2—C11	1.739 (4)	C15—C16	1.383 (5)
O1—C1	1.230 (5)	C15—H15	0.9300
O3—C8	1.242 (4)	C16—C17	1.380 (5)
O4—C8	1.251 (4)	C16—C20i	1.502 (5)
O6—H61	0.856 (17)	C17—C18	1.373 (6)
O6—H62	0.86 (2)	C17—H17	0.9300
O5—C20	1.237 (5)	C18—H18	0.9300
N1—C15	1.330 (4)	C19—C18	1.374 (5)
N1—C19	1.331 (5)	C19—H19	0.9300
N2—C21	1.461 (5)	C20—N2	1.340 (5)
N2—C23	1.476 (5)	C20—C16ii	1.502 (5)
C1—O2	1.265 (5)	C21—C22	1.521 (6)
C2—C1	1.509 (5)	C21—H21A	0.9700
C2—C3	1.381 (5)	C21—H21B	0.9700
C2—C7	1.368 (6)	C22—H22A	0.9600
C3—C4	1.380 (5)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600
C4—C5	1.372 (6)	C23—C24	1.500 (6)
C5—C6	1.368 (7)	C23—H23A	0.9700
C5—H5	0.9300	C23—H23B	0.9700
C6—H6	0.9300	C24—H24A	0.9600
C7—C6	1.389 (6)	C24—H24B	0.9600
C7—H7	0.9300	C24—H24C	0.9600
C9—C8	1.497 (5)
O1—Cd1—C1	26.54 (11)	C7—C6—H6	119.8
O1—Cd1—C8	161.03 (10)	C2—C7—C6	120.1 (4)
O2—Cd1—O1	53.75 (10)	C2—C7—H7	119.9
O2—Cd1—O3	135.22 (10)	C6—C7—H7	119.9
O2—Cd1—O4	81.10 (10)	O3—C8—Cd1	62.38 (19)
O2—Cd1—O5	81.83 (10)	O3—C8—O4	122.0 (3)
O2—Cd1—C1	27.21 (11)	O3—C8—C9	118.8 (3)
O2—Cd1—C8	108.24 (11)	O4—C8—Cd1	59.57 (19)
O3—Cd1—O1	170.39 (10)	O4—C8—C9	119.2 (3)
O3—Cd1—C1	162.33 (11)	C9—C8—Cd1	178.0 (3)
O3—Cd1—C8	27.04 (10)	C10—C9—C8	120.1 (3)
O4—Cd1—O1	134.15 (9)	C14—C9—C8	120.7 (3)
O4—Cd1—O3	54.23 (9)	C14—C9—C10	119.1 (3)
O4—Cd1—O5	94.28 (10)	C9—C10—H10	120.1
O4—Cd1—C1	108.10 (11)	C11—C10—C9	119.7 (4)
O4—Cd1—C8	27.19 (10)	C11—C10—H10	120.1
O5—Cd1—O1	87.40 (10)	C10—C11—Cl2	119.2 (3)
O5—Cd1—O3	97.07 (11)	C12—C11—C10	121.6 (4)
O5—Cd1—C1	83.43 (10)	C12—C11—Cl2	119.2 (3)
O5—Cd1—C8	96.30 (10)	C11—C12—C13	118.8 (4)
O6—Cd1—O1	84.21 (11)	C11—C12—H12	120.6
O6—Cd1—O2	97.43 (11)	C13—C12—H12	120.6
O6—Cd1—O3	90.46 (11)	C12—C13—H13	119.8
O6—Cd1—O4	95.42 (11)	C14—C13—C12	120.4 (4)
O6—Cd1—O5	170.03 (11)	C14—C13—H13	119.8
O6—Cd1—C1	91.39 (11)	C9—C14—H14	119.8
O6—Cd1—C8	93.37 (11)	C13—C14—C9	120.4 (4)
N1—Cd1—O1	86.30 (10)	C13—C14—H14	119.8
N1—Cd1—O2	136.21 (10)	N1—C15—C16	122.6 (3)
N1—Cd1—O3	86.21 (10)	N1—C15—H15	118.7
N1—Cd1—O4	139.00 (10)	C16—C15—H15	118.7
N1—Cd1—O5	78.90 (10)	C15—C16—C20i	123.4 (3)
N1—Cd1—O6	95.16 (10)	C17—C16—C15	118.4 (3)
N1—Cd1—C1	111.11 (11)	C17—C16—C20i	118.1 (3)
N1—Cd1—C8	112.67 (10)	C16—C17—H17	120.4
C8—Cd1—C1	135.29 (12)	C18—C17—C16	119.1 (3)
C1—O1—Cd1	88.1 (2)	C18—C17—H17	120.4
C1—O2—Cd1	95.6 (2)	C17—C18—C19	118.7 (4)
C8—O3—Cd1	90.6 (2)	C17—C18—H18	120.7
C8—O4—Cd1	93.2 (2)	C19—C18—H18	120.7
C20—O5—Cd1	124.3 (2)	N1—C19—C18	122.9 (4)
Cd1—O6—H61	107 (4)	N1—C19—H19	118.5
Cd1—O6—H62	103 (5)	C18—C19—H19	118.5
H61—O6—H62	107 (4)	O5—C20—N2	122.2 (4)
C15—N1—Cd1	122.3 (2)	O5—C20—C16ii	118.0 (3)
C15—N1—C19	118.2 (3)	N2—C20—C16ii	119.8 (3)
C19—N1—Cd1	119.0 (2)	N2—C21—C22	112.6 (4)
C20—N2—C21	125.2 (3)	N2—C21—H21A	109.1
C20—N2—C23	118.0 (4)	N2—C21—H21B	109.1
C21—N2—C23	116.5 (3)	C22—C21—H21A	109.1
O1—C1—Cd1	65.4 (2)	C22—C21—H21B	109.1
O1—C1—O2	122.5 (3)	H21A—C21—H21B	107.8
O1—C1—C2	119.7 (4)	C21—C22—H22A	109.5
O2—C1—Cd1	57.16 (19)	C21—C22—H22B	109.5
O2—C1—C2	117.7 (4)	C21—C22—H22C	109.5
C2—C1—Cd1	173.1 (3)	H22A—C22—H22B	109.5
C3—C2—C1	119.7 (3)	H22A—C22—H22C	109.5
C7—C2—C1	120.6 (4)	H22B—C22—H22C	109.5
C7—C2—C3	119.7 (3)	N2—C23—C24	112.3 (4)
C2—C3—H3	120.3	N2—C23—H23A	109.2
C4—C3—C2	119.5 (4)	N2—C23—H23B	109.2
C4—C3—H3	120.3	C24—C23—H23A	109.2
C3—C4—Cl1	120.2 (3)	C24—C23—H23B	109.2
C5—C4—Cl1	118.6 (3)	H23A—C23—H23B	107.9
C5—C4—C3	121.2 (4)	C23—C24—H24A	109.5
C4—C5—H5	120.5	C23—C24—H24B	109.5
C6—C5—C4	119.0 (4)	C23—C24—H24C	109.5
C6—C5—H5	120.5	H24A—C24—H24B	109.5
C5—C6—C7	120.5 (4)	H24A—C24—H24C	109.5
C5—C6—H6	119.8	H24B—C24—H24C	109.5
O2—Cd1—O1—C1	1.3 (2)	Cd1—O5—C20—N2	−109.6 (3)
O4—Cd1—O1—C1	13.0 (3)	Cd1—O5—C20—C16ii	72.2 (4)
O5—Cd1—O1—C1	−80.5 (2)	C15—N1—Cd1—O1	−9.4 (3)
O6—Cd1—O1—C1	104.9 (2)	C15—N1—Cd1—O2	−31.9 (3)
N1—Cd1—O1—C1	−159.5 (2)	C15—N1—Cd1—O3	164.6 (3)
C8—Cd1—O1—C1	21.4 (5)	C15—N1—Cd1—O4	178.8 (2)
O1—Cd1—O2—C1	−1.3 (2)	C15—N1—Cd1—O5	−97.5 (3)
O3—Cd1—O2—C1	−176.7 (2)	C15—N1—Cd1—O6	74.4 (3)
O4—Cd1—O2—C1	−172.8 (2)	C15—N1—Cd1—C1	−19.0 (3)
O5—Cd1—O2—C1	91.5 (2)	C15—N1—Cd1—C8	170.3 (3)
O6—Cd1—O2—C1	−78.4 (2)	C19—N1—Cd1—O1	163.1 (3)
N1—Cd1—O2—C1	27.0 (3)	C19—N1—Cd1—O2	140.6 (3)
C8—Cd1—O2—C1	−174.5 (2)	C19—N1—Cd1—O3	−22.9 (3)
O2—Cd1—O3—C8	4.5 (3)	C19—N1—Cd1—O4	−8.6 (4)
O4—Cd1—O3—C8	−0.2 (2)	C19—N1—Cd1—O5	75.1 (3)
O5—Cd1—O3—C8	90.0 (2)	C19—N1—Cd1—O6	−113.0 (3)
O6—Cd1—O3—C8	−96.5 (2)	C19—N1—Cd1—C1	153.5 (3)
N1—Cd1—O3—C8	168.3 (2)	C19—N1—Cd1—C8	−17.2 (3)
C1—Cd1—O3—C8	−0.5 (5)	Cd1—N1—C15—C16	173.3 (3)
O1—Cd1—O4—C8	174.0 (2)	C19—N1—C15—C16	0.7 (5)
O2—Cd1—O4—C8	−176.5 (2)	Cd1—N1—C19—C18	−174.4 (3)
O3—Cd1—O4—C8	0.2 (2)	C15—N1—C19—C18	−1.5 (6)
O5—Cd1—O4—C8	−95.5 (2)	C20—N2—C21—C22	−109.8 (5)
O6—Cd1—O4—C8	86.8 (2)	C23—N2—C21—C22	76.9 (5)
N1—Cd1—O4—C8	−17.5 (3)	C20—N2—C23—C24	−89.3 (5)
C1—Cd1—O4—C8	−179.9 (2)	C21—N2—C23—C24	84.5 (6)
O1—Cd1—C1—O2	177.7 (4)	O1—C1—O2—Cd1	2.4 (4)
O2—Cd1—C1—O1	−177.7 (4)	C2—C1—O2—Cd1	−174.6 (3)
O3—Cd1—C1—O1	−170.0 (3)	C3—C2—C1—O1	1.6 (5)
O3—Cd1—C1—O2	7.8 (5)	C3—C2—C1—O2	178.7 (3)
O4—Cd1—C1—O1	−170.3 (2)	C7—C2—C1—O1	−176.8 (4)
O4—Cd1—C1—O2	7.5 (2)	C7—C2—C1—O2	0.4 (5)
O5—Cd1—C1—O1	97.4 (2)	C1—C2—C3—C4	−177.5 (3)
O5—Cd1—C1—O2	−84.9 (2)	C7—C2—C3—C4	0.9 (6)
O6—Cd1—C1—O1	−74.1 (2)	C1—C2—C7—C6	177.9 (4)
O6—Cd1—C1—O2	103.6 (2)	C3—C2—C7—C6	−0.5 (6)
N1—Cd1—C1—O1	22.0 (3)	C2—C3—C4—Cl1	178.4 (3)
N1—Cd1—C1—O2	−160.3 (2)	C2—C3—C4—C5	−0.8 (6)
C8—Cd1—C1—O1	−170.3 (2)	Cl1—C4—C5—C6	−178.9 (4)
C8—Cd1—C1—O2	7.4 (3)	C3—C4—C5—C6	0.3 (7)
O1—Cd1—C8—O3	166.4 (3)	C4—C5—C6—C7	0.1 (7)
O1—Cd1—C8—O4	−13.3 (5)	C2—C7—C6—C5	0.0 (7)
O2—Cd1—C8—O3	−176.6 (2)	C10—C9—C8—O3	−11.4 (5)
O2—Cd1—C8—O4	3.7 (2)	C10—C9—C8—O4	170.1 (3)
O3—Cd1—C8—O4	−179.7 (4)	C14—C9—C8—O3	166.1 (4)
O4—Cd1—C8—O3	179.7 (4)	C14—C9—C8—O4	−12.4 (5)
O5—Cd1—C8—O3	−93.2 (2)	C8—C9—C10—C11	177.2 (3)
O5—Cd1—C8—O4	87.1 (2)	C14—C9—C10—C11	−0.3 (5)
O6—Cd1—C8—O3	84.4 (2)	C8—C9—C14—C13	−175.9 (4)
O6—Cd1—C8—O4	−95.3 (2)	C10—C9—C14—C13	1.6 (6)
N1—Cd1—C8—O3	−12.6 (3)	C9—C10—C11—Cl2	−179.9 (3)
N1—Cd1—C8—O4	167.7 (2)	C9—C10—C11—C12	−1.1 (6)
C1—Cd1—C8—O3	179.8 (2)	C10—C11—C12—C13	1.1 (7)
C1—Cd1—C8—O4	0.1 (3)	Cl2—C11—C12—C13	−180.0 (4)
Cd1—O1—C1—O2	−2.3 (4)	C11—C12—C13—C14	0.2 (7)
Cd1—O1—C1—C2	174.8 (3)	C9—C14—C13—C12	−1.6 (7)
Cd1—O3—C8—O4	0.3 (4)	N1—C15—C16—C17	1.3 (5)
Cd1—O3—C8—C9	−178.2 (3)	N1—C15—C16—C20i	176.9 (3)
Cd1—O4—C8—O3	−0.3 (4)	C15—C16—C17—C18	−2.4 (6)
Cd1—O4—C8—C9	178.1 (3)	C20i—C16—C17—C18	−178.4 (4)
C20—O5—Cd1—O1	91.2 (3)	C16—C17—C18—C19	1.7 (6)
C20—O5—Cd1—O2	37.5 (3)	N1—C19—C18—C17	0.3 (7)
C20—O5—Cd1—O3	−97.3 (3)	O5—C20—N2—C21	−173.2 (4)
C20—O5—Cd1—O4	−42.9 (3)	O5—C20—N2—C23	0.0 (5)
C20—O5—Cd1—N1	178.0 (3)	C16ii—C20—N2—C21	5.0 (5)
C20—O5—Cd1—C1	64.9 (3)	C16ii—C20—N2—C23	178.2 (3)
C20—O5—Cd1—C8	−70.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O2iii	0.85 (4)	1.94 (4)	2.753 (5)	160 (4)
O6—H62···O4iii	0.86 (4)	2.11 (4)	2.838 (4)	142 (5)
C15—H15···O1	0.93	2.52	3.181 (5)	128
C19—H19···O3	0.93	2.47	3.130 (5)	128

Table 1

Selected bond lengths (Å)

Cd1—O1	2.504 (3)
Cd1—O2	2.323 (3)
Cd1—O3	2.421 (3)
Cd1—O4	2.360 (3)
Cd1—O5	2.410 (3)
Cd1—O6	2.314 (3)
Cd1—N1	2.305 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H61⋯O2i	0.85 (4)	1.94 (4)	2.753 (5)	160 (4)
O6—H62⋯O4i	0.86 (4)	2.11 (4)	2.838 (4)	142 (5)
C15—H15⋯O1	0.93	2.52	3.181 (5)	128
C19—H19⋯O3	0.93	2.47	3.130 (5)	128

Symmetry code: (i) .