(Acetato-κ²O,O′)bis­(1,10-phenanthroline-κ²N,N′)cadmium(II) perchlorate dihydrate

In the title compound, [Cd(C₂H₄O₂)(C₁₂H₈N₂)₂]ClO₄·H₂O, the Cu^II ion is in a distorted octa­hedral coordination geometry with normal Cd—O and Cd—N bond lengths. The cation and anion both lie on crystallographic twofold axes. In the crystal structure, inter­molecular O—H...O hydrogen bonds form one-dimensional chains along [100] and in addition weak π–π stacking inter­actions connect mol­ecules along [001]. The Cg1 (central fused benzene ring) and Cg2 (outer fused pyridine ring) centroid–centroid and perpendicular distances are 3.746 (2) and 3.623 (2) Å, respectively, with Cg1...Cg2ⁱ = 3.602 (2) Å [symmety code: (i) −x, 1 − y, 1 − z].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• R factor = 0.059
• wR factor = 0.155
• Data-to-parameter ratio = 15.3

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S1. Comment

The formula unit of (I) comprises a monnuclear [Cd(phen)₂(CH ₃COO)]⁺ cation (Fig. 1), a perchlorate anion and a hydrate. The Cd ^II ion is in a distorted octahedral CdN₄O₂ geometry coordinated by four N atoms of phen ligands and two O atoms of a chelating bidentate acetato anion. By virtue of the twofold symmetry, atoms C13, C14, O1, O1b atoms are exactly planar (Zhang et al., 2003)[symmety code: (b) -x, y, 1/2 - z]. In the crystal structure, one-dimensional chains along [100] are formed by intermolecular O_water—H···O_perchlorate and O_water –H···O_water hydrogen bonds (Fig. 2. and Table 2). In addition weak π-π stacking interactions form chains along [001] as shown in Fig.3. Cg1 and Cg2 are the centroids defined by atoms C4/C5/C6/C7/C11/C12 and N2/C7/C8/C9/C10/C11, respectively. The relevant centroid–centroid and perpendicular distances defining these interactions are 3.746 (2), and 3.623 and 3.602 Å for Cg1··· Cg2ⁱ [symmety code:(i) -x,1 - y,1 - z].

Related literature

The structure of a related Cd complex has been published (Zhang et al. 2003).

S2. Experimental

Cd(CH₃COO)₂ ˙ 2(H₂ O)(0.266 g, 1 mmol), NaClO₄ (0.14 g, 1 mmol) phen (0.396 g, 2 mmol) were dissolved in a water-methanol solution (40 ml, 1:1). The mixture was refluxed for 4 h, and then filtered after cooling to room temperature. Single crystals of (I) were obtained after two weeks.

S3. Refinement

H atoms bonded to O atoms were located in difference maps and then included in the refinement with bond-length restraints of O – H = 0.82 (2) Å, with U_iso (H) = 1.5U_eq (O). H atoms bonded to C atoms were placed in calculated positions and included in the riding-model approximation, with C–H = 0.93—0.96 Å and U _iso(H) = 1.2U _eq (C of aromatic) or 1.5U _eq(C of methyl). Atoms O2/O3/O4 of the perchlorate anion are disordered over a twofold axis with equal occupancies. The largest peak of 1.18 Å^-3 in the final differnce Fourier is close to atom Cl1.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The cation of (I), with displacement ellipsoids drawn at the 50% probability level. The H atoms, disordered perchlorate and water molecules have been omitted for clarity. [symmetry code:(b) -x, y, 1/2 - z]
	Fig. 2. Part of the crystal structure of (I), showing the formation of hydrogen-bonded (dashed lines) one-dimensional chains.
	Fig. 3. Part of the crystal structure of (I), showing the formation of π-π stacking (dashed lines) interactions.

(Acetato-κ²O,O')bis(1,10-phenanthroline-κ²N,N')cadmium(II) perchlorate dihydrate

Crystal data

[Cd(C2H4O2)(C12H8N2)2]ClO4·2H2O	F(000) = 672
Mr = 667.33	Dx = 1.626 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3241 reflections
a = 9.887 (4) Å	θ = 2.2–23.0°
b = 8.177 (4) Å	µ = 0.96 mm^−1
c = 17.791 (7) Å	T = 298 K
β = 108.612 (19)°	Block, colorless
V = 1363.1 (10) Å^3	0.32 × 0.30 × 0.30 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	2584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −12→12
8986 measured reflections	k = −10→10
3118 independent reflections	l = −23→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0965P)^2] where P = (Fo^2 + 2Fc^2)/3
3118 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 1.27 e Å^−3
64 restraints	Δρmin = −0.59 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cd1	0.0000	0.53861 (6)	0.2500	0.0522 (2)
O1	−0.1072 (4)	0.2850 (5)	0.2079 (2)	0.0759 (10)
N1	−0.1344 (4)	0.6807 (5)	0.1392 (2)	0.0553 (9)
N2	0.1397 (4)	0.5700 (5)	0.1676 (2)	0.0551 (9)
C1	−0.2671 (6)	0.7337 (7)	0.1252 (3)	0.0695 (13)
H1	−0.3124	0.7125	0.1626	0.083*
C2	−0.3405 (7)	0.8187 (8)	0.0577 (4)	0.0831 (16)
H2	−0.4324	0.8569	0.0504	0.100*
C3	−0.2761 (7)	0.8454 (7)	0.0025 (4)	0.0840 (17)
H3	−0.3252	0.9008	−0.0439	0.101*
C4	−0.1383 (6)	0.7917 (6)	0.0134 (3)	0.0657 (13)
C5	−0.0647 (8)	0.8114 (8)	−0.0436 (3)	0.0844 (17)
H5	−0.1112	0.8633	−0.0914	0.101*
C6	0.0664 (8)	0.7584 (8)	−0.0305 (3)	0.0829 (18)
H6	0.1110	0.7770	−0.0685	0.099*
C7	0.1428 (6)	0.6720 (7)	0.0411 (3)	0.0663 (13)
C8	0.2802 (7)	0.6092 (8)	0.0557 (4)	0.0798 (17)
H8	0.3280	0.6230	0.0189	0.096*
C9	0.3412 (7)	0.5300 (9)	0.1227 (5)	0.0847 (19)
H9	0.4324	0.4875	0.1324	0.102*
C10	0.2714 (6)	0.5085 (8)	0.1795 (4)	0.0730 (14)
H10	0.3166	0.4511	0.2258	0.088*
C11	0.0762 (5)	0.6493 (5)	0.0986 (3)	0.0531 (10)
C12	−0.0698 (5)	0.7090 (5)	0.0842 (2)	0.0519 (10)
C13	0.0000	0.2084 (9)	0.2500	0.0667 (19)
C14	0.0000	0.0252 (12)	0.2500	0.130 (5)
H14A	−0.0764	−0.0139	0.2053	0.195*	0.50
H14B	−0.0130	−0.0139	0.2981	0.195*	0.50
H14C	0.0894	−0.0139	0.2466	0.195*	0.50
O1W	0.6176 (5)	0.2737 (11)	0.1119 (3)	0.130 (2)
O2	0.487 (2)	0.9428 (11)	0.3240 (6)	0.155 (6)	0.50
O3	0.6310 (13)	0.9327 (13)	0.2453 (14)	0.280 (14)	0.50
O4	0.3858 (18)	0.9310 (14)	0.1877 (9)	0.68 (6)	0.50
O5	0.5000	1.1640 (7)	0.2500	0.414 (15)
Cl1	0.5000	0.9901 (4)	0.2500	0.1092 (10)
H1WA	0.593 (9)	0.231 (12)	0.148 (4)	0.164*
H1WB	0.700 (6)	0.312 (12)	0.138 (4)	0.164*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.0537 (3)	0.0570 (3)	0.0476 (3)	0.000	0.0184 (2)	0.000
O1	0.078 (2)	0.070 (2)	0.071 (2)	−0.0126 (19)	0.0116 (19)	−0.0031 (19)
N1	0.053 (2)	0.057 (2)	0.055 (2)	−0.0023 (17)	0.0175 (17)	−0.0029 (17)
N2	0.048 (2)	0.061 (2)	0.057 (2)	−0.0040 (16)	0.0187 (17)	−0.0046 (17)
C1	0.058 (3)	0.075 (3)	0.073 (3)	0.007 (2)	0.018 (3)	0.001 (3)
C2	0.072 (4)	0.081 (4)	0.086 (4)	0.014 (3)	0.011 (3)	0.010 (3)
C3	0.089 (4)	0.075 (4)	0.070 (4)	0.010 (3)	0.000 (3)	0.009 (3)
C4	0.081 (3)	0.058 (3)	0.052 (3)	−0.008 (2)	0.012 (2)	−0.001 (2)
C5	0.113 (5)	0.084 (4)	0.053 (3)	−0.013 (4)	0.022 (3)	0.006 (3)
C6	0.117 (5)	0.087 (4)	0.058 (3)	−0.026 (4)	0.047 (3)	−0.011 (3)
C7	0.082 (3)	0.067 (3)	0.059 (3)	−0.022 (3)	0.035 (3)	−0.018 (2)
C8	0.080 (4)	0.093 (4)	0.082 (4)	−0.024 (3)	0.049 (3)	−0.027 (4)
C9	0.057 (3)	0.101 (5)	0.105 (5)	−0.004 (3)	0.038 (3)	−0.024 (4)
C10	0.056 (3)	0.085 (3)	0.081 (4)	0.002 (3)	0.026 (3)	−0.004 (3)
C11	0.058 (3)	0.052 (2)	0.050 (2)	−0.0127 (19)	0.019 (2)	−0.0140 (19)
C12	0.063 (3)	0.046 (2)	0.045 (2)	−0.0106 (19)	0.0150 (19)	−0.0072 (17)
C13	0.098 (6)	0.052 (4)	0.055 (4)	0.000	0.032 (4)	0.000
C14	0.194 (16)	0.055 (5)	0.131 (11)	0.000	0.039 (11)	0.000
O1W	0.069 (3)	0.202 (7)	0.113 (4)	0.007 (4)	0.020 (3)	0.048 (4)
O2	0.145 (9)	0.180 (10)	0.145 (9)	−0.008 (7)	0.050 (7)	0.058 (7)
O3	0.285 (16)	0.296 (17)	0.277 (16)	0.038 (10)	0.114 (11)	−0.010 (10)
O4	0.68 (6)	0.69 (6)	0.68 (6)	−0.009 (11)	0.22 (2)	−0.015 (11)
O5	0.424 (17)	0.394 (17)	0.439 (17)	0.000	0.158 (11)	0.000
Cl1	0.155 (3)	0.0983 (16)	0.101 (2)	0.000	0.078 (2)	0.000

Geometric parameters (Å, º)

Cd1—N1^i	2.308 (4)	C8—C9	1.320 (10)
Cd1—N1	2.308 (4)	C8—H8	0.9300
Cd1—N2^i	2.327 (4)	C9—C10	1.405 (9)
Cd1—N2	2.327 (4)	C9—H9	0.9300
Cd1—O1	2.341 (4)	C10—H10	0.9300
Cd1—O1^i	2.341 (4)	C11—C12	1.467 (6)
Cd1—C13	2.700 (7)	C13—O1^i	1.253 (5)
O1—C13	1.253 (5)	C13—C14	1.498 (11)
N1—C1	1.328 (6)	C14—H14A	0.9600
N1—C12	1.348 (6)	C14—H14B	0.9600
N2—C10	1.348 (7)	C14—H14C	0.9600
N2—C11	1.352 (6)	O1W—H1WA	0.84 (2)
C1—C2	1.376 (8)	O1W—H1WB	0.86 (2)
C1—H1	0.9300	O2—O4^ii	1.345 (17)
C2—C3	1.349 (9)	O2—O3^ii	1.403 (15)
C2—H2	0.9300	O2—Cl1	1.419 (5)
C3—C4	1.385 (8)	O3—O4^ii	1.254 (16)
C3—H3	0.9300	O3—O2^ii	1.403 (15)
C4—C12	1.399 (7)	O3—Cl1	1.405 (6)
C4—C5	1.434 (8)	O4—O3^ii	1.254 (16)
C5—C6	1.315 (9)	O4—O2^ii	1.345 (17)
C5—H5	0.9300	O4—Cl1	1.392 (6)
C6—C7	1.442 (9)	O5—Cl1	1.422 (6)
C6—H6	0.9300	Cl1—O4^ii	1.392 (6)
C7—C11	1.395 (6)	Cl1—O3^ii	1.405 (6)
C7—C8	1.397 (9)	Cl1—O2^ii	1.419 (5)
N1^i—Cd1—N1	119.55 (19)	C10—C9—H9	119.2
N1^i—Cd1—N2^i	72.68 (14)	N2—C10—C9	120.8 (6)
N1—Cd1—N2^i	100.75 (14)	N2—C10—H10	119.6
N1^i—Cd1—N2	100.75 (14)	C9—C10—H10	119.6
N1—Cd1—N2	72.68 (14)	N2—C11—C7	122.5 (5)
N2^i—Cd1—N2	167.32 (19)	N2—C11—C12	117.7 (4)
N1^i—Cd1—O1	142.90 (14)	C7—C11—C12	119.8 (5)
N1—Cd1—O1	95.42 (14)	N1—C12—C4	122.1 (5)
N2^i—Cd1—O1	89.99 (14)	N1—C12—C11	118.9 (4)
N2—Cd1—O1	101.29 (13)	C4—C12—C11	119.0 (4)
N1^i—Cd1—O1^i	95.42 (14)	O1^i—C13—O1	120.0 (7)
N1—Cd1—O1^i	142.90 (14)	O1^i—C13—C14	120.0 (3)
N2^i—Cd1—O1^i	101.29 (13)	O1—C13—C14	120.0 (3)
N2—Cd1—O1^i	89.99 (14)	O1^i—C13—Cd1	60.0 (3)
O1—Cd1—O1^i	55.2 (2)	O1—C13—Cd1	60.0 (3)
N1^i—Cd1—C13	120.22 (10)	C14—C13—Cd1	180.000 (1)
N1—Cd1—C13	120.22 (10)	C13—C14—H14A	109.5
N2^i—Cd1—C13	96.34 (9)	C13—C14—H14B	109.5
N2—Cd1—C13	96.34 (9)	H14A—C14—H14B	109.5
O1—Cd1—C13	27.62 (10)	C13—C14—H14C	109.5
O1^i—Cd1—C13	27.62 (10)	H14A—C14—H14C	109.5
C13—O1—Cd1	92.4 (4)	H14B—C14—H14C	109.5
C1—N1—C12	118.4 (4)	H1WA—O1W—H1WB	100 (3)
C1—N1—Cd1	126.2 (3)	O4^ii—O2—O3^ii	114.5 (10)
C12—N1—Cd1	115.5 (3)	O4^ii—O2—Cl1	60.4 (5)
C10—N2—C11	117.9 (4)	O3^ii—O2—Cl1	59.7 (4)
C10—N2—Cd1	126.7 (4)	O4^ii—O3—O2^ii	120.8 (10)
C11—N2—Cd1	115.3 (3)	O4^ii—O3—Cl1	62.8 (5)
N1—C1—C2	122.9 (5)	O2^ii—O3—Cl1	60.7 (4)
N1—C1—H1	118.5	O3^ii—O4—O2^ii	124.2 (10)
C2—C1—H1	118.5	O3^ii—O4—Cl1	63.9 (5)
C3—C2—C1	118.5 (6)	O2^ii—O4—Cl1	62.4 (5)
C3—C2—H2	120.7	O4^ii—Cl1—O4	139.3 (10)
C1—C2—H2	120.7	O4^ii—Cl1—O3	53.3 (7)
C2—C3—C4	121.2 (5)	O4—Cl1—O3	111.5 (5)
C2—C3—H3	119.4	O4^ii—Cl1—O3^ii	111.5 (5)
C4—C3—H3	119.4	O4—Cl1—O3^ii	53.3 (7)
C3—C4—C12	116.8 (5)	O3—Cl1—O3^ii	141.0 (10)
C3—C4—C5	124.3 (5)	O4^ii—Cl1—O2^ii	110.6 (5)
C12—C4—C5	118.8 (5)	O4—Cl1—O2^ii	57.2 (7)
C6—C5—C4	122.1 (5)	O3—Cl1—O2^ii	59.6 (6)
C6—C5—H5	118.9	O3^ii—Cl1—O2^ii	108.9 (5)
C4—C5—H5	118.9	O4^ii—Cl1—O2	57.2 (7)
C5—C6—C7	121.8 (5)	O4—Cl1—O2	110.6 (5)
C5—C6—H6	119.1	O3—Cl1—O2	108.9 (5)
C7—C6—H6	119.1	O3^ii—Cl1—O2	59.6 (6)
C11—C7—C8	118.3 (5)	O2^ii—Cl1—O2	148.3 (8)
C11—C7—C6	118.5 (5)	O4^ii—Cl1—O5	110.3 (5)
C8—C7—C6	123.2 (5)	O4—Cl1—O5	110.3 (5)
C9—C8—C7	119.0 (5)	O3—Cl1—O5	109.5 (5)
C9—C8—H8	120.5	O3^ii—Cl1—O5	109.5 (5)
C7—C8—H8	120.5	O2^ii—Cl1—O5	105.8 (4)
C8—C9—C10	121.5 (6)	O2—Cl1—O5	105.8 (4)
C8—C9—H9	119.2
N1^i—Cd1—O1—C13	−43.4 (3)	C1—N1—C12—C4	−0.1 (7)
N1—Cd1—O1—C13	155.4 (2)	Cd1—N1—C12—C4	179.1 (3)
N2^i—Cd1—O1—C13	−103.8 (2)	C1—N1—C12—C11	−179.3 (4)
N2—Cd1—O1—C13	82.0 (2)	Cd1—N1—C12—C11	0.0 (5)
O1^i—Cd1—O1—C13	0.0	C3—C4—C12—N1	0.7 (7)
N1^i—Cd1—N1—C1	−87.6 (4)	C5—C4—C12—N1	−177.5 (5)
N2^i—Cd1—N1—C1	−11.5 (4)	C3—C4—C12—C11	179.8 (4)
N2—Cd1—N1—C1	179.7 (4)	C5—C4—C12—C11	1.7 (7)
O1—Cd1—N1—C1	79.5 (4)	N2—C11—C12—N1	−0.9 (6)
O1^i—Cd1—N1—C1	114.1 (4)	C7—C11—C12—N1	177.6 (4)
C13—Cd1—N1—C1	92.4 (4)	N2—C11—C12—C4	179.9 (4)
N1^i—Cd1—N1—C12	93.3 (3)	C7—C11—C12—C4	−1.6 (6)
N2^i—Cd1—N1—C12	169.3 (3)	Cd1—O1—C13—O1^i	0.0
N2—Cd1—N1—C12	0.5 (3)	Cd1—O1—C13—C14	180.0
O1—Cd1—N1—C12	−99.7 (3)	N1^i—Cd1—C13—O1^i	−28.7 (2)
O1^i—Cd1—N1—C12	−65.1 (4)	N1—Cd1—C13—O1^i	151.3 (2)
C13—Cd1—N1—C12	−86.7 (3)	N2^i—Cd1—C13—O1^i	−102.3 (2)
N1^i—Cd1—N2—C10	65.9 (5)	N2—Cd1—C13—O1^i	77.7 (2)
N1—Cd1—N2—C10	−176.3 (5)	O1—Cd1—C13—O1^i	180.0
N2^i—Cd1—N2—C10	123.5 (4)	N1^i—Cd1—C13—O1	151.3 (2)
O1—Cd1—N2—C10	−84.0 (4)	N1—Cd1—C13—O1	−28.7 (2)
O1^i—Cd1—N2—C10	−29.6 (4)	N2^i—Cd1—C13—O1	77.7 (2)
C13—Cd1—N2—C10	−56.5 (4)	N2—Cd1—C13—O1	−102.3 (2)
N1^i—Cd1—N2—C11	−118.8 (3)	O1^i—Cd1—C13—O1	180.0
N1—Cd1—N2—C11	−1.0 (3)	O3^ii—O4—Cl1—O4^ii	80.3 (7)
N2^i—Cd1—N2—C11	−61.3 (3)	O2^ii—O4—Cl1—O4^ii	−83.8 (6)
O1—Cd1—N2—C11	91.2 (3)	O3^ii—O4—Cl1—O3	138.4 (12)
O1^i—Cd1—N2—C11	145.7 (3)	O2^ii—O4—Cl1—O3	−25.7 (10)
C13—Cd1—N2—C11	118.7 (3)	O2^ii—O4—Cl1—O3^ii	−164.2 (12)
C12—N1—C1—C2	−1.2 (8)	O3^ii—O4—Cl1—O2^ii	164.2 (12)
Cd1—N1—C1—C2	179.7 (5)	O3^ii—O4—Cl1—O2	17.1 (12)
N1—C1—C2—C3	1.9 (10)	O2^ii—O4—Cl1—O2	−147.1 (9)
C1—C2—C3—C4	−1.2 (10)	O3^ii—O4—Cl1—O5	−99.7 (7)
C2—C3—C4—C12	0.0 (9)	O2^ii—O4—Cl1—O5	96.2 (6)
C2—C3—C4—C5	178.1 (6)	O2^ii—O3—Cl1—O4^ii	161.4 (12)
C3—C4—C5—C6	180.0 (6)	O4^ii—O3—Cl1—O4	−136.3 (12)
C12—C4—C5—C6	−2.0 (9)	O2^ii—O3—Cl1—O4	25.0 (10)
C4—C5—C6—C7	2.1 (10)	O4^ii—O3—Cl1—O3^ii	−78.7 (8)
C5—C6—C7—C11	−2.0 (9)	O2^ii—O3—Cl1—O3^ii	82.7 (6)
C5—C6—C7—C8	177.8 (6)	O4^ii—O3—Cl1—O2^ii	−161.4 (12)
C11—C7—C8—C9	0.6 (8)	O4^ii—O3—Cl1—O2	−14.0 (11)
C6—C7—C8—C9	−179.2 (6)	O2^ii—O3—Cl1—O2	147.4 (9)
C7—C8—C9—C10	−0.4 (10)	O4^ii—O3—Cl1—O5	101.3 (8)
C11—N2—C10—C9	1.6 (8)	O2^ii—O3—Cl1—O5	−97.3 (6)
Cd1—N2—C10—C9	176.7 (4)	O3^ii—O2—Cl1—O4^ii	−152.0 (10)
C8—C9—C10—N2	−0.7 (10)	O4^ii—O2—Cl1—O4	136.2 (12)
C10—N2—C11—C7	−1.4 (7)	O3^ii—O2—Cl1—O4	−15.9 (11)
Cd1—N2—C11—C7	−177.1 (3)	O4^ii—O2—Cl1—O3	13.4 (11)
C10—N2—C11—C12	177.1 (4)	O3^ii—O2—Cl1—O3	−138.7 (11)
Cd1—N2—C11—C12	1.3 (5)	O4^ii—O2—Cl1—O3^ii	152.0 (10)
C8—C7—C11—N2	0.3 (7)	O4^ii—O2—Cl1—O2^ii	75.7 (7)
C6—C7—C11—N2	−179.9 (5)	O3^ii—O2—Cl1—O2^ii	−76.3 (6)
C8—C7—C11—C12	−178.1 (5)	O4^ii—O2—Cl1—O5	−104.3 (7)
C6—C7—C11—C12	1.7 (7)	O3^ii—O2—Cl1—O5	103.7 (6)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5^iii	0.84 (2)	2.34 (3)	3.165 (6)	168 (10)
O1W—H1WA···O2^iv	0.84 (2)	2.58 (8)	3.230 (13)	135 (9)
O1W—H1WB···O1^v	0.86 (2)	1.93 (6)	2.713 (6)	152 (10)

Symmetry codes: (iii) x, y−1, z; (iv) −x+1, y−1, −z+1/2; (v) x+1, y, z.