catena-Poly[[[aqua­(1,10-phenanthroline-κ2N,N′)cadmium(II)]-μ-pyridine-2,3-dicarboxyl­ato-κ4N,O2:O3,O3′] dihydrate]

Li, M.; Ha, W.; Chang, L.; Yuan, L.

doi:10.1107/S1600536808037203

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1554-m1555

doi:10.1107/S1600536808037203

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catena-Poly[[[aqua(1,10-phenanthroline-κ²N,N′)cadmium(II)]-μ-pyridine-2,3-dicarboxylato-κ⁴N,O²:O³,O^3′] dihydrate]

Ming Li,^a ^* Wuzu Ha,^a Liang Chang ^a and Liangjie Yuan ^b

^aDepartment of Chemical Engineering, Wuhan University of Science and Engineering, Wuhan 430073, People's Republic of China, and ^bCollege of Chemistry and Molecular Science, Wuhan University, Wuhan 430072, People's Republic of China
^*Correspondence e-mail: limwuse@163.com

(Received 9 October 2008; accepted 10 November 2008; online 20 November 2008)

The title complex, {[Cd(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·2H₂O}_n, is a one-dimensional coordination polymer, wherein the Cd atom is seven-coordinated by two 1,10-phenanthroline N atoms, one N and three O atoms from two different pyridine-2,3-dicarboxylate ligands, and one water molecule. It is further extended to a two-dimensional layer structure by hydrogen bonds and π–π stacking interactions [centroid-centroid distances of 3.560 (2) and 3.666 (2) Å]. There is a C4 water chain in the structure whose repeat unit contains four water molecules with O⋯O distances in the range 2.748 (3)–2.795 (4) Å. One of the two H atoms of each water of hydration is statistically distributed over two positions with equal occupancy.

Related literature

For potential applications of metal–organic coordination polymers, see: Moulton & Zaworotko (2001 ). For related structures, see: Gutschke et al. (1995 ); Li et al. (2006 ); Yu et al. (2004 ). For the structure of ice, see: Eisenberg & Kauzmann (1969 ).

Experimental

Crystal data

[Cd(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·2H₂O
M_r = 511.76
Triclinic, $[P \overline 1]$
a = 7.8154 (5) Å
b = 10.5854 (7) Å
c = 13.0681 (8) Å
α = 70.934 (1)°
β = 77.940 (1)°
γ = 68.698 (1)°
V = 946.98 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 293 (2) K
0.40 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.645, T_max = 0.840
6124 measured reflections
4194 independent reflections
3979 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.07
4194 reflections
272 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3W—H3W3⋯O2W	0.86	1.99	2.780 (3)	152
O3W—H2W3⋯O3Wⁱ	0.83	1.98	2.795 (4)	164
O3W—H1W3⋯O1ⁱⁱ	0.83	2.06	2.860 (2)	161
O2W—H1W2⋯O2ⁱⁱ	0.83	2.02	2.840 (2)	173
O2W—H3W2⋯O2Wⁱⁱⁱ	0.84	1.93	2.748 (3)	163
O2W—H2W2⋯O3W	0.86	1.98	2.780 (3)	155
O1W—H2W1⋯O2^iv	0.82	1.97	2.7784 (19)	168
O1W—H1W1⋯O3^v	0.86	1.90	2.751 (2)	167
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) x+1, y, z; (v) -x, -y, -z+2.

Data collection: SMART (Bruker, 2001 ); 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: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037203/pv2111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037203/pv2111Isup2.hkl

checkCIF report

Comment top

Metal-organic coordination polymers have been of great interest due to their intriguing potential applications, such as catalysis, magnetism, electronic and chemical separation (Moulton & Zaworotko, 2001). Multidentate N– or O-donor ligands, such as pyridine- or imidazole- (di)carboxylic acids, have drawn extensive attention in the construction of coordination polymers or metal-organic formworks (MOF). For example, pyridine or imidazole dicarboxyic acid ligands, including pyridine-2,6-, 2,5- or 3,4-dicarboxylic and imidazole-3,4-dicarboxylic acids, have been extensively employed in the construction of such metal-organic formworks. Comparing with other pyridine-dicarboxylic acids, pyridine-2,3-dicarboxylic acid (2,3-pydc) has been rarely used as a linkage ligand (Gutschke et al., 1995; Yu et al., 2004; Li et al., 2006). We have synthesized a novel one-dimensional (one-dimensional) coordination polymer based on 2,3-pydc, [Cd(2,3-pydc)(H₂O)(phen).2H₂O]_n (phen = 1,10-phenanthroline), (I), the crystal structure of which is presented in this article.

The title complex is a one-dimensional chain-like coordination polymer. In the structure of the title compound (Fig. 1), the Cd ion is seven-coordinated with two N atoms from phen, one N and three O atoms from two different pyridine-2,3-dicarboxylate and a water molecule. The 2,3-pydc affords four coordination atoms to connect two Cd ions, one as chelating bidentate through the N atom and one O atom of carboxylate in 2-position, the other with two O atoms of carboxylate in 3-position. Thus, complex (I) illustrates a one-dimensional chain structure along a axis, as shown in Fig. 2. Two adjacent chains band together by a series of hydrogen bonds involving water and carbonyl O-atoms (details are given in Table 1), π-π interaction of 1,10-phenanthroline with the shortest distance between the centroids of C11—C14/C18/C19 rings being 3.560 (2) Å and the shortest distance between the centroids of N3/C13—C17 rings are 3.666 (2) Å, thus resulting in a two-dimensional supramolecular structure. The structure also displays a short C6—O2···π(Cg(1)) interaction with a perpendicular distance between O2 and the centroid of Cg(1) being 3.562 (2) Å.

It is also worthwhile to note that there is a C4 water chain in (I), whose repeating unit contains four water molecules with O—O distances 2.750 (4) 2.782 (3), and 2.798 (4) Å (average distance = 2.777 Å), which are all close to the corresponding distance of O—O in the ice I_c (2.75 Å) and I_h (2.759 Å) determined at 143 and 183 K, respectively (Eisenberg & Kauzmann, 1969). Moreover, each water molecule links to the host by the H-bonding interaction between water of hydration and coordination water molecules. Water molecule can participate in four hydrogen bonds in a tetrahedral arrangement with two hydrogen atoms and two lone pairs, but also frequently show 3-coordinate configurations, just as in (I).

Related literature top

For potential applications of metal–organic coordination polymers, see: Moulton & Zaworotko (2001). For related structures, see: Gutschke et al. (1995); Li et al. (2006); Yu et al. (2004). For the structure of ice, see: Eisenberg & Kauzmann (1969).

Experimental top

CdO (0.05 mmol), 1,10-phenanthroline (0.05 mmol) and pyridine 2,3-dicarboxylic acid (0.10 mmol) were added into 1 ml water and stirred for 5 min in air, then transferred to a closed container. After reacting at 353 K for 7 days, the mixture was cooled to room temperature at a rate of 5 K/h. Colorless crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment of Cd in (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level; hydrogen atoms were omitted for clarity. Symmetry codes: a = x - 1, y, z; b = x + 1, y, z.
	Fig. 2. Unit cell packing of (I) showing (one-dimensional) chain-like structure along the a-axis; hydrogen bonds have been shown by dotted lines.

catena-Poly[[[aqua(1,10-phenanthroline- κ²N,N')cadmium(II)]-µ-pyridine-2,3-dicarboxylato- κ⁴N,O²:O³,O^3'] dihydrate] top

Crystal data top

[Cd(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·2H₂O	Z = 2
M_r = 511.76	F(000) = 512
Triclinic, P1	D_x = 1.795 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8154 (5) Å	Cell parameters from 4951 reflections
b = 10.5854 (7) Å	θ = 2.3–29.6°
c = 13.0681 (8) Å	µ = 1.20 mm⁻¹
α = 70.934 (1)°	T = 293 K
β = 77.940 (1)°	Rod-like, colorless
γ = 68.698 (1)°	0.40 × 0.16 × 0.15 mm
V = 946.98 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4194 independent reflections
Radiation source: fine-focus sealed tube	3979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.645, T_max = 0.840	k = −13→13
6124 measured reflections	l = −16→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.019	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0181P)² + 0.4298P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4194 reflections	Δρ_max = 0.28 e Å⁻³
272 parameters	Δρ_min = −0.27 e Å⁻³
8 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (5)

Crystal data top

[Cd(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·2H₂O	γ = 68.698 (1)°
M_r = 511.76	V = 946.98 (10) Å³
Triclinic, P1	Z = 2
a = 7.8154 (5) Å	Mo Kα radiation
b = 10.5854 (7) Å	µ = 1.20 mm⁻¹
c = 13.0681 (8) Å	T = 293 K
α = 70.934 (1)°	0.40 × 0.16 × 0.15 mm
β = 77.940 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4194 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3979 reflections with I > 2σ(I)
T_min = 0.645, T_max = 0.840	R_int = 0.012
6124 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	8 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.08	Δρ_max = 0.28 e Å⁻³
4194 reflections	Δρ_min = −0.27 e Å⁻³
272 parameters

Special details top

Experimental. Elemental analysis. Cacld. for C₁₉H₁₇CdN₃O₇: C, 44.55; H, 3.35; N, 8.21; Found: C, 44.05; H, 3.44; N, 8.53.

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.351199 (16)	0.150242 (13)	0.791379 (10)	0.02558 (5)
O1	0.03910 (18)	0.25289 (13)	0.83701 (12)	0.0341 (3)
O1W	0.3973 (2)	0.23034 (15)	0.92673 (11)	0.0386 (3)
H1W1	0.3765	0.1750	0.9897	0.046*
H2W1	0.5091	0.2167	0.9178	0.046*
O2	−0.23661 (17)	0.22382 (14)	0.87797 (12)	0.0347 (3)
O3	−0.39081 (19)	−0.04132 (16)	0.87081 (13)	0.0444 (4)
O4	−0.3121 (2)	0.10668 (15)	0.72263 (12)	0.0431 (3)
N1	0.2029 (2)	−0.02383 (15)	0.85619 (12)	0.0271 (3)
N2	0.2943 (2)	0.15794 (18)	0.61441 (14)	0.0370 (4)
N3	0.3212 (2)	0.37684 (16)	0.67259 (13)	0.0325 (3)
C1	0.0212 (2)	0.03040 (17)	0.84658 (13)	0.0228 (3)
C2	−0.0784 (2)	−0.04976 (17)	0.83637 (13)	0.0242 (3)
C3	0.0120 (3)	−0.19266 (19)	0.84791 (15)	0.0311 (4)
H3	−0.0519	−0.2500	0.8448	0.037*
C4	0.1965 (3)	−0.24943 (19)	0.86391 (16)	0.0336 (4)
H4	0.2575	−0.3455	0.8740	0.040*
C5	0.2886 (3)	−0.16083 (19)	0.86460 (16)	0.0319 (4)
H5	0.4147	−0.1976	0.8711	0.038*
C6	−0.0676 (2)	0.18204 (17)	0.85371 (13)	0.0240 (3)
C7	−0.2739 (2)	0.01160 (19)	0.80796 (15)	0.0286 (4)
C8	0.2799 (4)	0.0538 (3)	0.5853 (2)	0.0539 (6)
H8	0.2953	−0.0333	0.6367	0.065*
C9	0.2429 (4)	0.0683 (4)	0.4814 (2)	0.0711 (8)
H9	0.2360	−0.0079	0.4638	0.085*
C10	0.2171 (4)	0.1952 (4)	0.4069 (2)	0.0715 (9)
H10	0.1922	0.2067	0.3373	0.086*
C11	0.2277 (3)	0.3097 (3)	0.43373 (18)	0.0540 (6)
C12	0.2682 (3)	0.2858 (2)	0.54009 (15)	0.0371 (4)
C13	0.2814 (3)	0.4003 (2)	0.57072 (15)	0.0353 (4)
C14	0.2530 (3)	0.5338 (2)	0.49409 (18)	0.0483 (6)
C15	0.2690 (4)	0.6423 (2)	0.5264 (2)	0.0581 (7)
H15	0.2527	0.7313	0.4776	0.070*
C16	0.3084 (4)	0.6176 (2)	0.6286 (2)	0.0572 (7)
H16	0.3187	0.6892	0.6509	0.069*
C17	0.3331 (3)	0.4828 (2)	0.70002 (19)	0.0446 (5)
H17	0.3592	0.4667	0.7703	0.054*
C18	0.1968 (4)	0.4480 (4)	0.3597 (2)	0.0708 (9)
H18	0.1669	0.4643	0.2903	0.085*
C19	0.2102 (4)	0.5535 (4)	0.3882 (2)	0.0674 (8)
H19	0.1912	0.6418	0.3380	0.081*
O2W	0.3981 (2)	0.49790 (17)	0.09955 (14)	0.0559 (4)
H2W2	0.3059	0.4845	0.0842	0.067*	0.50
H1W2	0.3589	0.5781	0.1080	0.067*
H3W2	0.4562	0.5171	0.0376	0.067*	0.50
O3W	0.0437 (3)	0.49496 (17)	0.09995 (15)	0.0593 (5)
H1W3	−0.0028	0.5736	0.1119	0.071*
H2W3	−0.0031	0.4996	0.0465	0.071*	0.50
H3W3	0.1599	0.4814	0.0833	0.071*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02151 (8)	0.02702 (8)	0.02817 (8)	−0.00974 (5)	−0.00549 (5)	−0.00348 (5)
O1	0.0248 (7)	0.0268 (6)	0.0536 (8)	−0.0105 (5)	−0.0005 (6)	−0.0146 (6)
O1W	0.0330 (7)	0.0508 (8)	0.0362 (7)	−0.0193 (6)	−0.0036 (6)	−0.0105 (6)
O2	0.0216 (7)	0.0326 (7)	0.0505 (8)	−0.0084 (5)	0.0026 (6)	−0.0164 (6)
O3	0.0263 (7)	0.0505 (9)	0.0554 (9)	−0.0196 (7)	−0.0050 (6)	−0.0044 (7)
O4	0.0384 (8)	0.0416 (8)	0.0443 (8)	−0.0102 (7)	−0.0183 (6)	0.0002 (6)
N1	0.0205 (7)	0.0260 (7)	0.0348 (8)	−0.0076 (6)	−0.0066 (6)	−0.0058 (6)
N2	0.0356 (9)	0.0441 (9)	0.0339 (9)	−0.0136 (7)	−0.0041 (7)	−0.0127 (7)
N3	0.0307 (8)	0.0316 (8)	0.0301 (8)	−0.0100 (7)	0.0001 (6)	−0.0041 (6)
C1	0.0217 (8)	0.0235 (8)	0.0225 (8)	−0.0084 (6)	−0.0024 (6)	−0.0037 (6)
C2	0.0229 (8)	0.0242 (8)	0.0252 (8)	−0.0087 (7)	−0.0041 (6)	−0.0040 (6)
C3	0.0324 (10)	0.0255 (8)	0.0387 (10)	−0.0129 (7)	−0.0085 (8)	−0.0057 (7)
C4	0.0336 (10)	0.0225 (8)	0.0405 (10)	−0.0038 (7)	−0.0093 (8)	−0.0058 (7)
C5	0.0233 (9)	0.0284 (9)	0.0404 (10)	−0.0038 (7)	−0.0097 (7)	−0.0057 (8)
C6	0.0240 (8)	0.0245 (8)	0.0243 (8)	−0.0090 (7)	−0.0039 (6)	−0.0053 (6)
C7	0.0241 (9)	0.0285 (9)	0.0380 (10)	−0.0088 (7)	−0.0069 (7)	−0.0126 (7)
C8	0.0603 (16)	0.0619 (15)	0.0513 (14)	−0.0235 (13)	−0.0057 (11)	−0.0264 (12)
C9	0.078 (2)	0.097 (2)	0.0637 (18)	−0.0357 (18)	−0.0071 (15)	−0.0462 (18)
C10	0.0657 (18)	0.123 (3)	0.0417 (14)	−0.0371 (18)	−0.0068 (13)	−0.0351 (17)
C11	0.0397 (13)	0.0903 (19)	0.0300 (11)	−0.0203 (12)	−0.0050 (9)	−0.0136 (12)
C12	0.0250 (9)	0.0547 (12)	0.0268 (9)	−0.0103 (9)	−0.0025 (7)	−0.0077 (8)
C13	0.0230 (9)	0.0405 (10)	0.0294 (9)	−0.0057 (8)	0.0011 (7)	−0.0003 (8)
C14	0.0336 (11)	0.0488 (13)	0.0380 (11)	−0.0065 (10)	0.0012 (9)	0.0092 (9)
C15	0.0528 (15)	0.0359 (12)	0.0580 (15)	−0.0093 (11)	0.0093 (12)	0.0082 (10)
C16	0.0682 (17)	0.0346 (11)	0.0593 (15)	−0.0195 (11)	0.0141 (13)	−0.0098 (11)
C17	0.0519 (14)	0.0382 (11)	0.0418 (12)	−0.0191 (10)	0.0054 (10)	−0.0093 (9)
C18	0.0593 (17)	0.111 (3)	0.0266 (11)	−0.0262 (17)	−0.0137 (11)	0.0059 (14)
C19	0.0535 (16)	0.080 (2)	0.0391 (13)	−0.0158 (14)	−0.0086 (11)	0.0176 (13)
O2W	0.0545 (10)	0.0439 (9)	0.0604 (11)	−0.0030 (8)	−0.0024 (8)	−0.0191 (8)
O3W	0.0714 (12)	0.0408 (9)	0.0740 (12)	−0.0219 (8)	−0.0031 (10)	−0.0247 (8)

Geometric parameters (Å, º) top

Cd1—O1	2.3185 (13)	C4—H4	0.9300
Cd1—O1W	2.3336 (14)	C5—H5	0.9300
Cd1—N3	2.3513 (15)	C8—C9	1.395 (4)
Cd1—N1	2.3616 (14)	C8—H8	0.9300
Cd1—O3ⁱ	2.4049 (15)	C9—C10	1.351 (5)
Cd1—N2	2.4151 (16)	C9—H9	0.9300
Cd1—O4ⁱ	2.5189 (16)	C10—C11	1.400 (4)
O1—C6	1.256 (2)	C10—H10	0.9300
O1W—H1W1	0.8630	C11—C12	1.411 (3)
O1W—H2W1	0.8216	C11—C18	1.433 (4)
O2—C6	1.238 (2)	C12—C13	1.437 (3)
O3—C7	1.257 (2)	C13—C14	1.410 (3)
O3—Cd1ⁱⁱ	2.4049 (15)	C14—C15	1.399 (4)
O4—C7	1.238 (2)	C14—C19	1.422 (4)
O4—Cd1ⁱⁱ	2.5189 (16)	C15—C16	1.353 (4)
N1—C5	1.336 (2)	C15—H15	0.9300
N1—C1	1.341 (2)	C16—C17	1.396 (3)
N2—C8	1.324 (3)	C16—H16	0.9300
N2—C12	1.356 (3)	C17—H17	0.9300
N3—C17	1.322 (3)	C18—C19	1.331 (5)
N3—C13	1.353 (3)	C18—H18	0.9300
C1—C2	1.393 (2)	C19—H19	0.9300
C1—C6	1.526 (2)	O2W—H2W2	0.8556
C2—C3	1.389 (2)	O2W—H1W2	0.8277
C2—C7	1.501 (2)	O2W—H3W2	0.8415
C3—C4	1.377 (3)	O3W—H1W3	0.8306
C3—H3	0.9300	O3W—H2W3	0.8344
C4—C5	1.377 (3)	O3W—H3W3	0.8577

O1—Cd1—O1W	85.50 (5)	C4—C5—H5	118.9
O1—Cd1—N3	82.48 (5)	O2—C6—O1	125.52 (16)
O1W—Cd1—N3	87.94 (5)	O2—C6—C1	117.87 (15)
O1—Cd1—N1	70.02 (5)	O1—C6—C1	116.58 (15)
O1W—Cd1—N1	114.38 (5)	O4—C7—O3	122.84 (17)
N3—Cd1—N1	142.12 (5)	O4—C7—C2	119.52 (17)
O1—Cd1—O3ⁱ	139.09 (5)	O3—C7—C2	117.56 (16)
O1W—Cd1—O3ⁱ	78.30 (5)	N2—C8—C9	123.3 (3)
N3—Cd1—O3ⁱ	133.35 (5)	N2—C8—H8	118.4
N1—Cd1—O3ⁱ	82.89 (5)	C9—C8—H8	118.4
O1—Cd1—N2	91.39 (5)	C10—C9—C8	118.7 (3)
O1W—Cd1—N2	158.39 (6)	C10—C9—H9	120.6
N3—Cd1—N2	70.46 (6)	C8—C9—H9	120.6
N1—Cd1—N2	84.31 (6)	C9—C10—C11	120.5 (2)
O3ⁱ—Cd1—N2	116.44 (6)	C9—C10—H10	119.8
O1—Cd1—O4ⁱ	164.61 (5)	C11—C10—H10	119.8
O1W—Cd1—O4ⁱ	88.95 (5)	C10—C11—C12	117.3 (2)
N3—Cd1—O4ⁱ	82.98 (5)	C10—C11—C18	123.3 (2)
N1—Cd1—O4ⁱ	125.23 (5)	C12—C11—C18	119.3 (3)
O3ⁱ—Cd1—O4ⁱ	52.80 (5)	N2—C12—C11	121.9 (2)
N2—Cd1—O4ⁱ	88.50 (5)	N2—C12—C13	119.02 (17)
C6—O1—Cd1	118.77 (11)	C11—C12—C13	119.1 (2)
Cd1—O1W—H1W1	109.3	N3—C13—C14	121.7 (2)
Cd1—O1W—H2W1	103.1	N3—C13—C12	118.94 (17)
H1W1—O1W—H2W1	105.8	C14—C13—C12	119.32 (19)
C7—O3—Cd1ⁱⁱ	93.36 (11)	C15—C14—C13	117.7 (2)
C7—O4—Cd1ⁱⁱ	88.54 (12)	C15—C14—C19	122.6 (2)
C5—N1—C1	119.41 (15)	C13—C14—C19	119.7 (3)
C5—N1—Cd1	124.26 (12)	C16—C15—C14	119.9 (2)
C1—N1—Cd1	112.35 (11)	C16—C15—H15	120.0
C8—N2—C12	118.31 (19)	C14—C15—H15	120.0
C8—N2—Cd1	127.04 (16)	C15—C16—C17	118.9 (2)
C12—N2—Cd1	114.59 (13)	C15—C16—H16	120.5
C17—N3—C13	118.51 (18)	C17—C16—H16	120.5
C17—N3—Cd1	124.53 (14)	N3—C17—C16	123.2 (2)
C13—N3—Cd1	116.90 (13)	N3—C17—H17	118.4
N1—C1—C2	121.67 (15)	C16—C17—H17	118.4
N1—C1—C6	115.02 (14)	C19—C18—C11	121.4 (2)
C2—C1—C6	123.23 (15)	C19—C18—H18	119.3
C3—C2—C1	117.80 (16)	C11—C18—H18	119.3
C3—C2—C7	118.66 (15)	C18—C19—C14	121.2 (2)
C1—C2—C7	123.46 (15)	C18—C19—H19	119.4
C4—C3—C2	120.00 (17)	C14—C19—H19	119.4
C4—C3—H3	120.0	H2W2—O2W—H1W2	105.8
C2—C3—H3	120.0	H2W2—O2W—H3W2	101.4
C3—C4—C5	118.55 (16)	H1W2—O2W—H3W2	97.7
C3—C4—H4	120.7	H1W3—O3W—H2W3	106.6
C5—C4—H4	120.7	H1W3—O3W—H3W3	107.2
N1—C5—C4	122.22 (17)	H2W3—O3W—H3W3	109.5
N1—C5—H5	118.9

O1W—Cd1—O1—C6	−131.03 (14)	Cd1—N1—C5—C4	−155.90 (15)
N3—Cd1—O1—C6	140.47 (14)	C3—C4—C5—N1	3.7 (3)
N1—Cd1—O1—C6	−13.05 (13)	Cd1—O1—C6—O2	−179.59 (14)
O3ⁱ—Cd1—O1—C6	−64.70 (16)	Cd1—O1—C6—C1	2.4 (2)
N2—Cd1—O1—C6	70.38 (14)	N1—C1—C6—O2	−158.83 (16)
O4ⁱ—Cd1—O1—C6	159.78 (16)	C2—C1—C6—O2	18.1 (2)
O1—Cd1—N1—C5	179.92 (16)	N1—C1—C6—O1	19.4 (2)
O1W—Cd1—N1—C5	−104.93 (15)	C2—C1—C6—O1	−163.76 (16)
N3—Cd1—N1—C5	133.86 (14)	Cd1ⁱⁱ—O4—C7—O3	15.87 (19)
O3ⁱ—Cd1—N1—C5	−31.25 (15)	Cd1ⁱⁱ—O4—C7—C2	−167.34 (15)
N2—Cd1—N1—C5	86.36 (15)	Cd1ⁱⁱ—O3—C7—O4	−16.7 (2)
O4ⁱ—Cd1—N1—C5	2.24 (17)	Cd1ⁱⁱ—O3—C7—C2	166.48 (13)
O1—Cd1—N1—C1	22.61 (11)	C3—C2—C7—O4	−119.5 (2)
O1W—Cd1—N1—C1	97.76 (12)	C1—C2—C7—O4	57.2 (3)
N3—Cd1—N1—C1	−23.44 (17)	C3—C2—C7—O3	57.5 (2)
O3ⁱ—Cd1—N1—C1	171.45 (13)	C1—C2—C7—O3	−125.86 (19)
N2—Cd1—N1—C1	−70.95 (12)	C12—N2—C8—C9	1.3 (4)
O4ⁱ—Cd1—N1—C1	−155.06 (11)	Cd1—N2—C8—C9	178.6 (2)
O1—Cd1—N2—C8	−98.04 (19)	N2—C8—C9—C10	−1.2 (4)
O1W—Cd1—N2—C8	−179.31 (17)	C8—C9—C10—C11	0.0 (5)
N3—Cd1—N2—C8	−179.6 (2)	C9—C10—C11—C12	0.8 (4)
N1—Cd1—N2—C8	−28.28 (19)	C9—C10—C11—C18	−178.2 (3)
O3ⁱ—Cd1—N2—C8	50.9 (2)	C8—N2—C12—C11	−0.4 (3)
O4ⁱ—Cd1—N2—C8	97.4 (2)	Cd1—N2—C12—C11	−178.00 (16)
O1—Cd1—N2—C12	79.33 (14)	C8—N2—C12—C13	179.3 (2)
O1W—Cd1—N2—C12	−1.9 (2)	Cd1—N2—C12—C13	1.7 (2)
N3—Cd1—N2—C12	−2.19 (13)	C10—C11—C12—N2	−0.6 (3)
N1—Cd1—N2—C12	149.10 (14)	C18—C11—C12—N2	178.4 (2)
O3ⁱ—Cd1—N2—C12	−131.76 (13)	C10—C11—C12—C13	179.6 (2)
O4ⁱ—Cd1—N2—C12	−85.28 (14)	C18—C11—C12—C13	−1.3 (3)
O1—Cd1—N3—C17	85.52 (17)	C17—N3—C13—C14	0.1 (3)
O1W—Cd1—N3—C17	−0.21 (17)	Cd1—N3—C13—C14	177.42 (15)
N1—Cd1—N3—C17	128.57 (16)	C17—N3—C13—C12	179.96 (18)
O3ⁱ—Cd1—N3—C17	−71.96 (19)	Cd1—N3—C13—C12	−2.7 (2)
N2—Cd1—N3—C17	179.69 (18)	N2—C12—C13—N3	0.6 (3)
O4ⁱ—Cd1—N3—C17	−89.41 (17)	C11—C12—C13—N3	−179.66 (18)
O1—Cd1—N3—C13	−91.62 (13)	N2—C12—C13—C14	−179.52 (18)
O1W—Cd1—N3—C13	−177.35 (13)	C11—C12—C13—C14	0.2 (3)
N1—Cd1—N3—C13	−48.57 (17)	N3—C13—C14—C15	0.6 (3)
O3ⁱ—Cd1—N3—C13	110.90 (14)	C12—C13—C14—C15	−179.3 (2)
N2—Cd1—N3—C13	2.56 (13)	N3—C13—C14—C19	−179.6 (2)
O4ⁱ—Cd1—N3—C13	93.46 (13)	C12—C13—C14—C19	0.6 (3)
C5—N1—C1—C2	−5.2 (3)	C13—C14—C15—C16	−0.8 (4)
Cd1—N1—C1—C2	153.32 (13)	C19—C14—C15—C16	179.4 (2)
C5—N1—C1—C6	171.73 (16)	C14—C15—C16—C17	0.3 (4)
Cd1—N1—C1—C6	−29.74 (17)	C13—N3—C17—C16	−0.6 (3)
N1—C1—C2—C3	6.6 (3)	Cd1—N3—C17—C16	−177.74 (18)
C6—C1—C2—C3	−170.04 (16)	C15—C16—C17—N3	0.5 (4)
N1—C1—C2—C7	−170.04 (16)	C10—C11—C18—C19	−179.3 (3)
C6—C1—C2—C7	13.3 (3)	C12—C11—C18—C19	1.7 (4)
C1—C2—C3—C4	−2.9 (3)	C11—C18—C19—C14	−1.0 (4)
C7—C2—C3—C4	173.96 (17)	C15—C14—C19—C18	179.6 (3)
C2—C3—C4—C5	−2.0 (3)	C13—C14—C19—C18	−0.2 (4)
C1—N1—C5—C4	−0.1 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H3W3···O2W	0.86	1.99	2.780 (3)	152
O3W—H2W3···O3Wⁱⁱⁱ	0.83	1.98	2.795 (4)	164
O3W—H1W3···O1^iv	0.83	2.06	2.860 (2)	161
O2W—H1W2···O2^iv	0.83	2.02	2.840 (2)	173
O2W—H3W2···O2W^v	0.84	1.93	2.748 (3)	163
O2W—H2W2···O3W	0.86	1.98	2.780 (3)	155
O1W—H2W1···O2ⁱ	0.82	1.97	2.7784 (19)	168
O1W—H1W1···O3^vi	0.86	1.90	2.751 (2)	167

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

Experimental details

Crystal data
Chemical formula	[Cd(C₇H₃NO₄)(C₁₂H₈N₂)(H₂O)]·2H₂O
M_r	511.76
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8154 (5), 10.5854 (7), 13.0681 (8)
α, β, γ (°)	70.934 (1), 77.940 (1), 68.698 (1)
V (Å³)	946.98 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.40 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.645, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	6124, 4194, 3979
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.08
No. of reflections	4194
No. of parameters	272
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H3W3···O2W	0.86	1.99	2.780 (3)	152.3
O3W—H2W3···O3Wⁱ	0.83	1.98	2.795 (4)	164.1
O3W—H1W3···O1ⁱⁱ	0.83	2.06	2.860 (2)	161.4
O2W—H1W2···O2ⁱⁱ	0.83	2.02	2.840 (2)	173.4
O2W—H3W2···O2Wⁱⁱⁱ	0.84	1.93	2.748 (3)	162.8
O2W—H2W2···O3W	0.86	1.98	2.780 (3)	154.7
O1W—H2W1···O2^iv	0.82	1.97	2.7784 (19)	168.4
O1W—H1W1···O3^v	0.86	1.90	2.751 (2)	166.7

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

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (grant No. 20671074) and the Foundation of the Education Department of Hubei Province (No. Q20081705).

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eisenberg, D. & Kauzmann, W. (1969). The Structure and Properties of Water. Oxford University Press. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gutschke, S. O. H., Slawin, A. M. Z. & Wood, P. T. (1995). J. Chem. Soc. Chem. Commun. pp. 2197–2198. CrossRef Web of Science Google Scholar
Li, M., Xiang, J. F., Yuan, L. J., Wu, S. M., Chen, S. P. & Sun, J. T. (2006). Cryst. Growth Des. 9, 2036–2040. Web of Science CSD CrossRef Google Scholar
Moulton, B. & Zaworotko, M. (2001). Chem. Rev. 101, 1629–1658. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, Z. T., Liao, Z. L., Jiang, Y. S., Li, G. H., Li, G. D. & Chen, J. S. (2004). Chem. Commun. pp. 1814–1815. Web of Science CSD CrossRef Google Scholar

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