catena-Poly[[aqua­bis­[2-(3-benzoyl­phen­yl)propano­ato-κ2O1,O1′]cadmium(II)]-μ-4,4′-bipyridine-κ2N:N′]

Jiang, T.; Ng, S.W.

doi:10.1107/S1600536811001280

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m209

doi:10.1107/S1600536811001280

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catena-Poly[[aquabis[2-(3-benzoylphenyl)propanoato-κ²O¹,O^1′]cadmium(II)]-μ-4,4′-bipyridine-κ²N:N′]

Tao Jiang ^a and Seik Weng Ng ^b ^*

^aDepartment of Food and Environmental Engineering, Heilongjiang East University, Harbin 150086, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 January 2011; accepted 10 January 2011; online 15 January 2011)

The 4,4′-bipyridine heterocycle in the polymeric title compound, [Cd(C₁₆H₁₃O₃)₂(C₁₀H₈N₂)(H₂O)]_n, links adjacent Cd(II) ions into a chain running along the c axis. The Cd atom, which lies on a twofold rotation axis, is chelated by the carboxylate unit and exists in a seven-coordinate pentagonal–bipyramidal geometry. The apical sites are occupied by N atoms. The water molecule also lies on the twofold rotation axis. The methyl substituent of the propanoate group is disordered over two positions in a 1:1 ratio. O—H⋯O hydrogen bonding between water molecules and adjacent carboxylate O atoms is observed.

Related literature

For the crystal structure of the parent carboxylic acid, see: Briard & Rossi (1990 ). For related metal carboxylates, see: Zhang et al. (2007a ,b ).

Experimental

Crystal data

[Cd(C₁₆H₁₃O₃)₂(C₁₀H₈N₂)(H₂O)]
M_r = 793.13
Monoclinic, C 2/c
a = 28.3242 (5) Å
b = 6.2561 (2) Å
c = 23.6171 (4) Å
β = 119.539 (1)°
V = 3640.97 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 293 K
0.21 × 0.17 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.875, T_max = 0.908
25489 measured reflections
4128 independent reflections
3904 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.083
S = 1.10
4128 reflections
246 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1⋯O2ⁱ	0.84	2.09	2.741 (3)	135
Symmetry code: (i) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001280/hg2790sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001280/hg2790Isup2.hkl

checkCIF report

Comment top

The drug, 2-(3-benzoylphenyl)propanoic acid (Kétoprofène) (Briard & Rossi, 1990), forms a small number of metal derivatives; in the cobalt(II) and nickel(II) derivatives, the carboxyl unit binds in a unidentate manner to the water-coordinated metal atoms (Zhang et al., 2007a, 2007b). In the title cadmium–4,4'-bipyridine adduct (Scheme I), the N-heterocycle links adjacent formula units into a chain running along the c-axis of the monoclinic unit cell. The cadmium atom, which lies on a twofold rotation axis, is chelated by the carboxyl unit and it exists in seven-coordinate pentagonal bipyramidal geometry. The apical sites are occupied by N atoms. The water molecule also lies on the twofold rotation axis (Fig. 1). The methyl subsituent of the carboxylate is disordered over two positions in a 1:1 ratio.

Related literature top

For the crystal structure of the parent carboxylic acid, see: Briard & Rossi (1990). For related metal carboxylates, see: Zhang et al. (2007a, 2007b).

Experimental top

Cadmium nitrate (1 mmol) and 4,4'-bipyridine (1 mmol) were dissolved in ethanol (50 ml); the solution was added to an aqueous solution (50 ml) of 2-(3-benzoylphenyl)propanoic acid (2 mmol). The pH was adjusted to 7 by the addition of aqueous sodium hydroxide. The solution was filtered and then set aside for the growth of crystal.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of fragment of the polymeric Cd(H₂O)(C₁₀H₈N₂)(C₁₆H₁₃O₃)₂ chain at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

catena-Poly[[aquabis[2-(3-benzoylphenyl)propanoato- κ²O¹,O^1']cadmium(II)]-µ-4,4'-bipyridine- κ²N:N'] top

Crystal data top

[Cd(C₁₆H₁₃O₃)₂(C₁₀H₈N₂)(H₂O)]	F(000) = 1624
M_r = 793.13	D_x = 1.447 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 24003 reflections
a = 28.3242 (5) Å	θ = 3.2–27.4°
b = 6.2561 (2) Å	µ = 0.65 mm⁻¹
c = 23.6171 (4) Å	T = 293 K
β = 119.539 (1)°	Prism, colorless
V = 3640.97 (15) Å³	0.21 × 0.17 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4128 independent reflections
Radiation source: fine-focus sealed tube	3904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.4°, θ_min = 3.2°
ω scans	h = −36→33
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→8
T_min = 0.875, T_max = 0.908	l = −29→30
25489 measured reflections

Refinement top

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0418P)² + 4.0713P] where P = (F_o² + 2F_c²)/3
4128 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.86 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Cd(C₁₆H₁₃O₃)₂(C₁₀H₈N₂)(H₂O)]	V = 3640.97 (15) Å³
M_r = 793.13	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.3242 (5) Å	µ = 0.65 mm⁻¹
b = 6.2561 (2) Å	T = 293 K
c = 23.6171 (4) Å	0.21 × 0.17 × 0.15 mm
β = 119.539 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4128 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3904 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.908	R_int = 0.023
25489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.083	H-atom parameters constrained
S = 1.10	Δρ_max = 0.86 e Å⁻³
4128 reflections	Δρ_min = −0.32 e Å⁻³
246 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.5000	0.57510 (3)	0.7500	0.03727 (8)
O1	0.40639 (7)	0.6179 (3)	0.67563 (9)	0.0607 (5)
O2	0.43201 (9)	0.2876 (3)	0.70014 (11)	0.0704 (5)
O3	0.40988 (11)	0.0777 (4)	0.45591 (12)	0.0850 (7)
O1W	0.5000	0.9428 (4)	0.7500	0.0785 (10)
H1	0.4679	0.9876	0.7303	0.118*
N1	0.50515 (8)	0.5506 (3)	0.65299 (9)	0.0442 (4)
C1	0.39770 (10)	0.4249 (5)	0.66638 (11)	0.0532 (6)
C2	0.34256 (14)	0.3558 (9)	0.60990 (15)	0.1154 (18)
H2	0.3500	0.2034	0.6086	0.138*	0.50
H2'	0.3186	0.4612	0.6136	0.138*	0.50
C3	0.3003 (2)	0.3399 (14)	0.6217 (3)	0.0763 (17)	0.50
H3A	0.3135	0.2957	0.6659	0.114*	0.50
H3B	0.2747	0.2366	0.5927	0.114*	0.50
H3C	0.2828	0.4764	0.6147	0.114*	0.50
C3'	0.3174 (3)	0.1758 (11)	0.6087 (3)	0.0765 (18)	0.50
H3'1	0.3217	0.1494	0.6511	0.115*	0.50
H3'2	0.3328	0.0595	0.5967	0.115*	0.50
H3'3	0.2795	0.1883	0.5775	0.115*	0.50
C4	0.33928 (11)	0.4258 (6)	0.54630 (13)	0.0717 (10)
C5	0.35646 (10)	0.2915 (5)	0.51355 (11)	0.0600 (7)
H5	0.3699	0.1568	0.5304	0.072*
C6	0.35392 (10)	0.3555 (4)	0.45536 (11)	0.0512 (5)
C7	0.33546 (11)	0.5580 (4)	0.43111 (13)	0.0561 (6)
H7	0.3340	0.6025	0.3927	0.067*
C8	0.31913 (12)	0.6943 (6)	0.46458 (15)	0.0712 (8)
H8	0.3070	0.8312	0.4488	0.085*
C9	0.32088 (12)	0.6274 (7)	0.52109 (16)	0.0799 (10)
H9	0.3094	0.7198	0.5428	0.096*
C10	0.37381 (11)	0.2037 (4)	0.42323 (12)	0.0561 (6)
C11	0.34975 (11)	0.2039 (4)	0.35106 (12)	0.0523 (5)
C12	0.29677 (12)	0.2666 (5)	0.30938 (14)	0.0625 (7)
H12	0.2751	0.3145	0.3262	0.075*
C13	0.27593 (15)	0.2578 (6)	0.24244 (15)	0.0805 (9)
H13	0.2404	0.3000	0.2144	0.097*
C14	0.30791 (18)	0.1868 (6)	0.21779 (16)	0.0863 (11)
H14	0.2938	0.1803	0.1730	0.104*
C15	0.36051 (17)	0.1253 (6)	0.25842 (18)	0.0837 (10)
H15	0.3821	0.0796	0.2412	0.100*
C16	0.38120 (13)	0.1315 (5)	0.32456 (15)	0.0671 (7)
H16	0.4166	0.0868	0.3520	0.080*
C17	0.47859 (10)	0.6901 (4)	0.60522 (10)	0.0496 (5)
H17	0.4608	0.8029	0.6125	0.060*
C18	0.47596 (10)	0.6764 (4)	0.54526 (10)	0.0492 (5)
H18	0.4571	0.7794	0.5136	0.059*
C19	0.50120 (9)	0.5111 (4)	0.53218 (9)	0.0419 (4)
C20	0.52919 (13)	0.3651 (5)	0.58225 (12)	0.0653 (8)
H20	0.5471	0.2503	0.5762	0.078*
C21	0.53023 (13)	0.3917 (5)	0.64114 (12)	0.0634 (8)
H21	0.5495	0.2932	0.6741	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04538 (13)	0.04118 (13)	0.02536 (11)	0.000	0.01752 (9)	0.000
O1	0.0547 (10)	0.0751 (14)	0.0467 (10)	0.0085 (9)	0.0207 (8)	−0.0110 (9)
O2	0.0836 (14)	0.0608 (13)	0.0684 (12)	−0.0055 (11)	0.0386 (11)	−0.0031 (10)
O3	0.1018 (17)	0.0817 (16)	0.0668 (14)	0.0390 (13)	0.0380 (13)	0.0248 (11)
O1W	0.0694 (18)	0.0446 (16)	0.093 (2)	0.000	0.0182 (18)	0.000
N1	0.0528 (10)	0.0534 (12)	0.0303 (8)	0.0050 (8)	0.0236 (8)	0.0042 (7)
C1	0.0472 (12)	0.082 (2)	0.0352 (11)	−0.0121 (12)	0.0238 (10)	−0.0136 (11)
C2	0.077 (2)	0.227 (5)	0.0424 (15)	−0.081 (3)	0.0299 (15)	−0.035 (2)
C3	0.046 (3)	0.108 (5)	0.070 (4)	−0.010 (3)	0.025 (3)	−0.004 (4)
C3'	0.087 (4)	0.084 (5)	0.058 (3)	−0.036 (4)	0.035 (3)	−0.007 (3)
C4	0.0467 (13)	0.121 (3)	0.0383 (13)	−0.0263 (16)	0.0142 (11)	−0.0198 (15)
C5	0.0533 (13)	0.0784 (19)	0.0374 (11)	−0.0092 (12)	0.0139 (10)	0.0032 (12)
C6	0.0487 (12)	0.0573 (14)	0.0383 (11)	−0.0031 (11)	0.0144 (9)	0.0004 (10)
C7	0.0565 (14)	0.0568 (16)	0.0402 (12)	−0.0005 (11)	0.0124 (10)	−0.0020 (10)
C8	0.0612 (15)	0.069 (2)	0.0603 (17)	0.0041 (14)	0.0122 (13)	−0.0176 (14)
C9	0.0555 (16)	0.114 (3)	0.0595 (18)	−0.0091 (17)	0.0202 (13)	−0.0391 (19)
C10	0.0635 (14)	0.0530 (15)	0.0495 (13)	0.0027 (12)	0.0260 (11)	0.0097 (11)
C11	0.0624 (14)	0.0463 (14)	0.0490 (13)	−0.0069 (11)	0.0282 (11)	0.0004 (10)
C12	0.0649 (15)	0.0590 (17)	0.0550 (14)	−0.0027 (12)	0.0228 (12)	−0.0084 (12)
C13	0.089 (2)	0.069 (2)	0.0538 (16)	−0.0030 (17)	0.0120 (15)	−0.0080 (14)
C14	0.124 (3)	0.082 (2)	0.0515 (16)	−0.014 (2)	0.0419 (19)	−0.0025 (16)
C15	0.107 (3)	0.093 (3)	0.076 (2)	−0.019 (2)	0.064 (2)	−0.0076 (19)
C16	0.0711 (17)	0.0711 (19)	0.0688 (18)	−0.0083 (14)	0.0420 (15)	−0.0003 (14)
C17	0.0615 (13)	0.0566 (15)	0.0361 (11)	0.0146 (11)	0.0282 (10)	0.0063 (10)
C18	0.0603 (13)	0.0560 (14)	0.0334 (10)	0.0153 (11)	0.0247 (10)	0.0113 (9)
C19	0.0490 (11)	0.0509 (12)	0.0291 (10)	0.0035 (9)	0.0217 (8)	0.0042 (9)
C20	0.101 (2)	0.0636 (17)	0.0439 (13)	0.0355 (16)	0.0457 (14)	0.0172 (12)
C21	0.096 (2)	0.0645 (17)	0.0384 (12)	0.0317 (15)	0.0397 (13)	0.0189 (11)

Geometric parameters (Å, º) top

Cd1—O1W	2.301 (3)	C6—C7	1.382 (4)
Cd1—O1ⁱ	2.3653 (18)	C6—C10	1.489 (4)
Cd1—O1	2.3653 (18)	C7—C8	1.388 (4)
Cd1—N1	2.3713 (17)	C7—H7	0.9300
Cd1—N1ⁱ	2.3713 (17)	C8—C9	1.376 (5)
Cd1—O2	2.469 (2)	C8—H8	0.9300
Cd1—O2ⁱ	2.469 (2)	C9—H9	0.9300
O1—C1	1.230 (3)	C10—C11	1.491 (3)
O2—C1	1.247 (4)	C11—C12	1.385 (4)
O3—C10	1.218 (3)	C11—C16	1.393 (4)
O1W—H1	0.8400	C12—C13	1.390 (4)
N1—C17	1.328 (3)	C12—H12	0.9300
N1—C21	1.329 (3)	C13—C14	1.370 (5)
C1—C2	1.534 (4)	C13—H13	0.9300
C2—C3'	1.325 (6)	C14—C15	1.371 (6)
C2—C3	1.360 (6)	C14—H14	0.9300
C2—C4	1.523 (4)	C15—C16	1.372 (4)
C2—H2	0.9800	C15—H15	0.9300
C2—H2'	0.9800	C16—H16	0.9300
C3—H3A	0.9600	C17—C18	1.384 (3)
C3—H3B	0.9600	C17—H17	0.9300
C3—H3C	0.9600	C18—C19	1.376 (3)
C3'—H3'1	0.9600	C18—H18	0.9300
C3'—H3'2	0.9600	C19—C20	1.392 (3)
C3'—H3'3	0.9600	C19—C19ⁱⁱ	1.494 (4)
C4—C9	1.382 (5)	C20—C21	1.387 (3)
C4—C5	1.383 (4)	C20—H20	0.9300
C5—C6	1.399 (3)	C21—H21	0.9300
C5—H5	0.9300

O1W—Cd1—O1ⁱ	83.50 (5)	C2—C3'—H3'3	109.5
O1W—Cd1—O1	83.50 (5)	H3'1—C3'—H3'3	109.5
O1ⁱ—Cd1—O1	167.01 (11)	H3'2—C3'—H3'3	109.5
O1W—Cd1—N1	93.71 (5)	C9—C4—C5	118.4 (3)
O1ⁱ—Cd1—N1	98.30 (7)	C9—C4—C2	120.9 (4)
O1—Cd1—N1	82.55 (7)	C5—C4—C2	120.7 (4)
O1W—Cd1—N1ⁱ	93.71 (5)	C4—C5—C6	120.9 (3)
O1ⁱ—Cd1—N1ⁱ	82.55 (7)	C4—C5—H5	119.5
O1—Cd1—N1ⁱ	98.30 (7)	C6—C5—H5	119.5
N1—Cd1—N1ⁱ	172.58 (10)	C7—C6—C5	119.7 (3)
O1W—Cd1—O2	136.77 (6)	C7—C6—C10	122.3 (2)
O1ⁱ—Cd1—O2	139.63 (8)	C5—C6—C10	118.0 (3)
O1—Cd1—O2	53.34 (8)	C6—C7—C8	119.4 (3)
N1—Cd1—O2	84.10 (7)	C6—C7—H7	120.3
N1ⁱ—Cd1—O2	90.49 (7)	C8—C7—H7	120.3
O1W—Cd1—O2ⁱ	136.77 (6)	C9—C8—C7	120.2 (3)
O1ⁱ—Cd1—O2ⁱ	53.34 (8)	C9—C8—H8	119.9
O1—Cd1—O2ⁱ	139.63 (8)	C7—C8—H8	119.9
N1—Cd1—O2ⁱ	90.49 (7)	C8—C9—C4	121.4 (3)
N1ⁱ—Cd1—O2ⁱ	84.10 (7)	C8—C9—H9	119.3
O2—Cd1—O2ⁱ	86.47 (11)	C4—C9—H9	119.3
C1—O1—Cd1	94.23 (16)	O3—C10—C6	120.0 (2)
C1—O2—Cd1	88.96 (17)	O3—C10—C11	119.5 (3)
Cd1—O1W—H1	109.5	C6—C10—C11	120.5 (2)
C17—N1—C21	116.76 (19)	C12—C11—C16	118.8 (3)
C17—N1—Cd1	119.96 (15)	C12—C11—C10	122.5 (2)
C21—N1—Cd1	123.07 (15)	C16—C11—C10	118.7 (3)
O1—C1—O2	122.6 (2)	C11—C12—C13	120.1 (3)
O1—C1—C2	117.4 (3)	C11—C12—H12	120.0
O2—C1—C2	120.0 (3)	C13—C12—H12	120.0
O1—C1—Cd1	59.23 (13)	C14—C13—C12	119.8 (3)
O2—C1—Cd1	64.04 (14)	C14—C13—H13	120.1
C2—C1—Cd1	169.56 (19)	C12—C13—H13	120.1
C3'—C2—C3	54.9 (5)	C13—C14—C15	120.8 (3)
C3'—C2—C4	116.9 (4)	C13—C14—H14	119.6
C3—C2—C4	126.2 (4)	C15—C14—H14	119.6
C3'—C2—C1	124.3 (5)	C14—C15—C16	119.7 (3)
C3—C2—C1	117.7 (4)	C14—C15—H15	120.1
C4—C2—C1	108.5 (2)	C16—C15—H15	120.1
C3'—C2—H2	45.1	C15—C16—C11	120.8 (3)
C3—C2—H2	99.2	C15—C16—H16	119.6
C4—C2—H2	99.2	C11—C16—H16	119.6
C1—C2—H2	99.2	N1—C17—C18	123.4 (2)
C3'—C2—H2'	100.7	N1—C17—H17	118.3
C3—C2—H2'	46.6	C18—C17—H17	118.3
C4—C2—H2'	100.7	C19—C18—C17	120.3 (2)
C1—C2—H2'	100.7	C19—C18—H18	119.9
H2—C2—H2'	145.7	C17—C18—H18	119.9
C2—C3—H3A	109.5	C18—C19—C20	116.36 (19)
C2—C3—H3B	109.5	C18—C19—C19ⁱⁱ	122.0 (3)
H3A—C3—H3B	109.5	C20—C19—C19ⁱⁱ	121.6 (3)
C2—C3—H3C	109.5	C21—C20—C19	119.7 (2)
H3A—C3—H3C	109.5	C21—C20—H20	120.2
H3B—C3—H3C	109.5	C19—C20—H20	120.2
C2—C3'—H3'1	109.5	N1—C21—C20	123.5 (2)
C2—C3'—H3'2	109.5	N1—C21—H21	118.3
H3'1—C3'—H3'2	109.5	C20—C21—H21	118.3

O1W—Cd1—O1—C1	177.46 (15)	Cd1—C1—C2—C4	−2.5 (18)
O1ⁱ—Cd1—O1—C1	177.46 (15)	C3'—C2—C4—C9	126.0 (6)
N1—Cd1—O1—C1	82.84 (15)	C3—C2—C4—C9	61.3 (7)
N1ⁱ—Cd1—O1—C1	−89.72 (15)	C1—C2—C4—C9	−87.2 (4)
O2—Cd1—O1—C1	−5.33 (14)	C3'—C2—C4—C5	−56.3 (6)
O2ⁱ—Cd1—O1—C1	0.9 (2)	C3—C2—C4—C5	−120.9 (7)
C1ⁱ—Cd1—O1—C1	−7.4 (4)	C1—C2—C4—C5	90.5 (4)
O1W—Cd1—O2—C1	9.29 (18)	C9—C4—C5—C6	−1.7 (4)
O1ⁱ—Cd1—O2—C1	−175.73 (14)	C2—C4—C5—C6	−179.5 (2)
O1—Cd1—O2—C1	5.24 (14)	C4—C5—C6—C7	1.9 (4)
N1—Cd1—O2—C1	−79.84 (15)	C4—C5—C6—C10	179.2 (2)
N1ⁱ—Cd1—O2—C1	105.24 (15)	C5—C6—C7—C8	−0.7 (4)
O2ⁱ—Cd1—O2—C1	−170.71 (18)	C10—C6—C7—C8	−177.9 (3)
C1ⁱ—Cd1—O2—C1	−175.28 (10)	C6—C7—C8—C9	−0.6 (4)
O1W—Cd1—N1—C17	−37.10 (19)	C7—C8—C9—C4	0.7 (5)
O1ⁱ—Cd1—N1—C17	−121.1 (2)	C5—C4—C9—C8	0.4 (4)
O1—Cd1—N1—C17	45.85 (19)	C2—C4—C9—C8	178.2 (3)
O2—Cd1—N1—C17	99.6 (2)	C7—C6—C10—O3	147.3 (3)
O2ⁱ—Cd1—N1—C17	−174.0 (2)	C5—C6—C10—O3	−29.9 (4)
O1W—Cd1—N1—C21	148.4 (2)	C7—C6—C10—C11	−32.9 (4)
O1ⁱ—Cd1—N1—C21	64.5 (2)	C5—C6—C10—C11	149.9 (2)
O1—Cd1—N1—C21	−128.6 (2)	O3—C10—C11—C12	151.6 (3)
O2—Cd1—N1—C21	−74.9 (2)	C6—C10—C11—C12	−28.2 (4)
O2ⁱ—Cd1—N1—C21	11.5 (2)	O3—C10—C11—C16	−26.2 (4)
C1—Cd1—N1—C21	−101.9 (2)	C6—C10—C11—C16	154.0 (3)
C1ⁱ—Cd1—N1—C21	37.7 (2)	C16—C11—C12—C13	−0.4 (4)
Cd1—O1—C1—O2	10.1 (3)	C10—C11—C12—C13	−178.1 (3)
Cd1—O1—C1—C2	−168.7 (2)	C11—C12—C13—C14	0.1 (5)
Cd1—O2—C1—O1	−9.6 (3)	C12—C13—C14—C15	−0.4 (6)
Cd1—O2—C1—C2	169.1 (2)	C13—C14—C15—C16	1.1 (6)
O1W—Cd1—C1—O1	−2.68 (16)	C14—C15—C16—C11	−1.4 (5)
O1ⁱ—Cd1—C1—O1	−177.57 (14)	C12—C11—C16—C15	1.0 (5)
N1—Cd1—C1—O1	−93.06 (15)	C10—C11—C16—C15	178.9 (3)
N1ⁱ—Cd1—C1—O1	93.98 (15)	C21—N1—C17—C18	0.2 (4)
O2—Cd1—C1—O1	170.6 (2)	Cd1—N1—C17—C18	−174.6 (2)
O2ⁱ—Cd1—C1—O1	−179.35 (14)	N1—C17—C18—C19	0.6 (4)
O1—C1—C2—C3'	−150.3 (5)	C17—C18—C19—C20	−0.8 (4)
O2—C1—C2—C3'	30.9 (6)	C17—C18—C19—C19ⁱⁱ	179.3 (3)
Cd1—C1—C2—C3'	141.2 (14)	C18—C19—C20—C21	0.2 (5)
O1—C1—C2—C3	−85.7 (6)	C19ⁱⁱ—C19—C20—C21	−179.9 (3)
O2—C1—C2—C3	95.5 (6)	C17—N1—C21—C20	−0.9 (5)
Cd1—C1—C2—C3	−154.1 (13)	Cd1—N1—C21—C20	173.8 (3)
O1—C1—C2—C4	65.9 (4)	C19—C20—C21—N1	0.7 (5)
O2—C1—C2—C4	−112.9 (4)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O2ⁱⁱⁱ	0.84	2.09	2.741 (3)	135

Symmetry code: (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₆H₁₃O₃)₂(C₁₀H₈N₂)(H₂O)]
M_r	793.13
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.3242 (5), 6.2561 (2), 23.6171 (4)
β (°)	119.539 (1)
V (Å³)	3640.97 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.21 × 0.17 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.875, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	25489, 4128, 3904
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.10
No. of reflections	4128
No. of parameters	246
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.32

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O2ⁱ	0.84	2.09	2.741 (3)	135

Symmetry code: (i) x, y+1, z.

Acknowledgements

We thank Heilongjiang East University and the University of Malaya for supporting this study.

References

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