Poly[[aqua-(μ(4)-1H-benzimidazole-5,6-dicarboxyl-ato-κN:O:O:O)(N,N-dimethyl-formamide-κO)cadmium(II)] dihydrate].

In the title compound, {[Cd(C(9)H(4)N(2)O(4))(C(3)H(7)NO)(H(2)O)]·2H(2)O}(n), the Cd(II) atom is coordinated by one N atom and three O atoms from four different 1H-benzimidazole-5,6-dicarboxyl-ate (Hbidc) ligands, one O atom from one dimethyl-formamide ligand, and one O atom from a water mol-ecule in a distorted octa-hedral geometry. The Hbidc ligands connect the Cd atoms into a two-dimensional network parallel to (001). N-H⋯O and O-H⋯O hydrogen bonds involving the water molecules are observed in the crystal structure.

Related literature

For related structures of 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Song, Wang, Hu et al. (2009 ▶); Song, Wang, Li et al. (2009 ▶); Song, Wang, Qin et al. (2009 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

[Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2O

M = 443.69

Triclinic,

a = 7.7729 (16) Å

b = 9.1648 (18) Å

c = 11.458 (2) Å

α = 102.76 (3)°

β = 97.70 (3)°

γ = 94.96 (3)°

V = 783.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.44 mm−1

T = 293 K

0.29 × 0.25 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.680, T max = 0.752

6197 measured reflections

2800 independent reflections

1539 reflections with I > 2σ(I)

R int = 0.121

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.223

S = 1.14

2800 reflections

219 parameters

9 restraints

H-atom parameters constrained

Δρmax = 2.12 e Å−3

Δρmin = −1.80 e Å−3

Data collection: CrystalStructure (Rigaku/MSC, 2002 ▶); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003065/hy2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003065/hy2275Isup2.hkl

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

[Cd(C9H4N2O4)(C3H7NO)(H2O)]·2H2O	Z = 2
Mr = 443.69	F(000) = 444
Triclinic, P1	Dx = 1.881 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7729 (16) Å	Cell parameters from 3441 reflections
b = 9.1648 (18) Å	θ = 3.3–27.4°
c = 11.458 (2) Å	µ = 1.44 mm−1
α = 102.76 (3)°	T = 293 K
β = 97.70 (3)°	Block, colorless
γ = 94.96 (3)°	0.29 × 0.25 × 0.21 mm
V = 783.2 (3) Å3

Rigaku/MSC Mercury CCD diffractometer	2800 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
graphite	Rint = 0.121
ω scans	θmax = 25.2°, θmin = 3.3°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −9→7
Tmin = 0.680, Tmax = 0.752	k = −10→10
6197 measured reflections	l = −13→13

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.223	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0683P)2 + 2.7388P] where P = (Fo2 + 2Fc2)/3
2800 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 2.12 e Å−3
9 restraints	Δρmin = −1.80 e Å−3

	x	y	z	Uiso*/Ueq
Cd1	0.32811 (14)	0.19007 (13)	0.58926 (9)	0.0427 (4)
O1	0.1397 (12)	0.1778 (11)	0.7248 (7)	0.043 (2)
O2	−0.1244 (11)	0.1608 (11)	0.7803 (8)	0.043 (2)
O1W	0.5202 (9)	0.0812 (8)	0.7112 (7)	0.045 (3)
O10	0.4501 (13)	0.4197 (11)	0.7028 (8)	0.048 (3)
N1	−0.1716 (14)	0.7274 (13)	0.5549 (9)	0.037 (3)
N2	0.0418 (16)	0.7573 (12)	0.7100 (10)	0.046 (3)
H2	0.1247	0.8019	0.7676	0.055*
N3	0.6296 (17)	0.5826 (15)	0.8605 (11)	0.057 (4)
C1	−0.0542 (18)	0.8220 (17)	0.6334 (13)	0.044 (4)
H1	−0.0382	0.9245	0.6362	0.053*
C2	−0.1506 (16)	0.5900 (15)	0.5837 (12)	0.035 (3)
C3	−0.2450 (15)	0.4482 (15)	0.5278 (10)	0.031 (3)
H3	−0.3353	0.4370	0.4633	0.037*
C4	−0.1988 (17)	0.3261 (16)	0.5722 (11)	0.037 (3)
C5	−0.0634 (17)	0.3421 (14)	0.6700 (11)	0.033 (3)
C6	0.0295 (17)	0.4860 (17)	0.7241 (12)	0.045 (4)
H6	0.1203	0.4999	0.7887	0.054*
C7	−0.0192 (16)	0.6032 (16)	0.6778 (10)	0.033 (3)
C8	−0.0144 (18)	0.2164 (15)	0.7258 (12)	0.039 (3)
C11	0.758 (3)	0.606 (2)	0.9664 (14)	0.086 (6)
H11A	0.7649	0.5123	0.9907	0.128*
H11B	0.7250	0.6793	1.0306	0.128*
H11C	0.8693	0.6407	0.9491	0.128*
C12	0.587 (2)	0.713 (2)	0.8183 (16)	0.077 (6)
H12A	0.5613	0.6868	0.7313	0.116*
H12B	0.6835	0.7907	0.8445	0.116*
H12C	0.4859	0.7477	0.8506	0.116*
C10	0.560 (2)	0.4477 (19)	0.7957 (13)	0.054 (4)
H10	0.5975	0.3655	0.8226	0.065*
O3W	0.7681 (13)	0.2252 (9)	1.0089 (11)	0.127 (6)
H5W	0.8465	0.2124	0.9650	0.190*
H6W	0.6998	0.1446	0.9891	0.190*
O2W	0.2935 (7)	0.0032 (12)	0.8739 (9)	0.080 (4)
H3W	0.3906	0.0207	0.8522	0.120*
H4W	0.2273	0.0510	0.8364	0.120*
C9	−0.2912 (17)	0.1756 (17)	0.5120 (11)	0.036 (3)
O3	−0.2155 (12)	0.0562 (10)	0.5048 (7)	0.041 (2)
O4	−0.4532 (9)	0.1698 (8)	0.4625 (7)	0.043 (2)
H1W	0.6279	0.1081	0.7315	0.065*
H2W	0.4982	−0.0084	0.6711	0.065*

	U11	U22	U33	U12	U13	U23
Cd1	0.0451 (7)	0.0367 (7)	0.0457 (6)	−0.0036 (5)	0.0070 (4)	0.0115 (5)
O1	0.040 (6)	0.042 (6)	0.043 (5)	−0.015 (5)	0.005 (4)	0.013 (4)
O2	0.033 (5)	0.041 (6)	0.059 (6)	−0.002 (5)	0.007 (4)	0.024 (5)
O1W	0.040 (5)	0.038 (6)	0.049 (5)	−0.017 (5)	0.006 (4)	0.004 (5)
O10	0.054 (6)	0.044 (7)	0.039 (5)	−0.003 (5)	−0.005 (5)	0.006 (5)
N1	0.035 (6)	0.030 (7)	0.042 (6)	0.000 (6)	0.000 (5)	0.006 (5)
N2	0.056 (8)	0.023 (7)	0.053 (7)	−0.007 (6)	0.011 (6)	0.002 (6)
N3	0.062 (9)	0.034 (8)	0.064 (8)	0.003 (7)	−0.009 (7)	0.004 (7)
C1	0.048 (9)	0.035 (9)	0.064 (9)	0.014 (7)	0.021 (8)	0.031 (8)
C2	0.030 (7)	0.029 (8)	0.057 (8)	0.011 (6)	0.020 (6)	0.020 (7)
C3	0.025 (6)	0.043 (9)	0.023 (6)	−0.010 (6)	0.001 (5)	0.010 (6)
C4	0.035 (8)	0.040 (9)	0.034 (7)	−0.009 (7)	0.003 (6)	0.009 (6)
C5	0.045 (8)	0.022 (7)	0.033 (7)	0.002 (6)	0.006 (6)	0.008 (6)
C6	0.032 (8)	0.055 (10)	0.043 (8)	−0.006 (7)	−0.007 (6)	0.016 (7)
C7	0.029 (7)	0.047 (9)	0.029 (7)	0.016 (7)	0.003 (5)	0.016 (6)
C8	0.041 (9)	0.027 (8)	0.043 (8)	−0.011 (7)	0.010 (6)	−0.002 (6)
C11	0.105 (16)	0.080 (15)	0.052 (10)	0.008 (12)	−0.028 (10)	0.001 (10)
C12	0.083 (14)	0.063 (14)	0.078 (12)	0.011 (11)	0.036 (10)	−0.013 (10)
C10	0.065 (11)	0.049 (11)	0.049 (9)	0.012 (9)	0.009 (8)	0.009 (8)
O3W	0.171 (17)	0.126 (15)	0.085 (10)	−0.006 (12)	0.049 (10)	0.020 (10)
O2W	0.075 (8)	0.090 (10)	0.088 (8)	0.009 (7)	0.027 (7)	0.041 (8)
C9	0.037 (8)	0.044 (9)	0.030 (7)	0.006 (7)	0.008 (6)	0.015 (6)
O3	0.056 (6)	0.028 (6)	0.039 (5)	0.000 (5)	0.011 (4)	0.005 (4)
O4	0.044 (6)	0.037 (6)	0.041 (5)	−0.009 (5)	0.008 (4)	−0.001 (4)

Cd1—N1i	2.226 (11)	C3—C4	1.382 (19)
Cd1—O10	2.266 (9)	C3—H3	0.9300
Cd1—O1	2.287 (8)	C4—C5	1.404 (18)
Cd1—O3ii	2.314 (9)	C4—C9	1.472 (18)
Cd1—O1W	2.344 (9)	C5—C6	1.414 (18)
Cd1—O4iii	2.373 (7)	C5—C8	1.489 (19)
O1—C8	1.278 (16)	C6—C7	1.359 (19)
O2—C8	1.261 (14)	C6—H6	0.9300
O1W—H1W	0.8380	C11—H11A	0.9600
O1W—H2W	0.8382	C11—H11B	0.9600
O10—C10	1.236 (17)	C11—H11C	0.9600
N1—C1	1.301 (17)	C12—H12A	0.9600
N1—C2	1.388 (17)	C12—H12B	0.9600
N2—C1	1.346 (17)	C12—H12C	0.9600
N2—C7	1.400 (17)	C10—H10	0.9300
N2—H2	0.8600	O3W—H5W	0.8411
N3—C10	1.320 (19)	O3W—H6W	0.8398
N3—C11	1.426 (19)	O2W—H3W	0.8389
N3—C12	1.43 (2)	O2W—H4W	0.8393
C1—H1	0.9300	C9—O3	1.279 (16)
C2—C7	1.359 (18)	C9—O4	1.302 (14)
C2—C3	1.407 (17)
N1i—Cd1—O10	96.6 (4)	C3—C4—C9	118.6 (11)
N1i—Cd1—O1	103.1 (4)	C5—C4—C9	119.8 (13)
O10—Cd1—O1	89.6 (3)	C4—C5—C6	119.5 (13)
N1i—Cd1—O3ii	90.6 (4)	C4—C5—C8	123.9 (12)
O10—Cd1—O3ii	172.6 (3)	C6—C5—C8	116.6 (12)
O1—Cd1—O3ii	86.9 (3)	C7—C6—C5	117.3 (12)
N1i—Cd1—O1W	169.1 (3)	C7—C6—H6	121.3
O10—Cd1—O1W	88.5 (3)	C5—C6—H6	121.3
O1—Cd1—O1W	86.5 (3)	C6—C7—C2	124.0 (13)
O3ii—Cd1—O1W	84.8 (3)	C6—C7—N2	132.0 (12)
N1i—Cd1—O4iii	85.9 (3)	C2—C7—N2	103.9 (12)
O10—Cd1—O4iii	93.7 (3)	O2—C8—O1	123.0 (14)
O1—Cd1—O4iii	170.0 (3)	O2—C8—C5	117.4 (13)
O3ii—Cd1—O4iii	88.7 (3)	O1—C8—C5	119.3 (11)
O1W—Cd1—O4iii	84.1 (3)	N3—C11—H11A	109.5
C8—O1—Cd1	130.4 (8)	N3—C11—H11B	109.5
H1W—O1W—H2W	112.2	H11A—C11—H11B	109.5
C10—O10—Cd1	127.5 (11)	N3—C11—H11C	109.5
C1—N1—C2	103.9 (12)	H11A—C11—H11C	109.5
C1—N1—Cd1i	118.8 (10)	H11B—C11—H11C	109.5
C2—N1—Cd1i	137.1 (9)	N3—C12—H12A	109.5
C1—N2—C7	106.8 (11)	N3—C12—H12B	109.5
C1—N2—H2	126.6	H12A—C12—H12B	109.5
C7—N2—H2	126.6	N3—C12—H12C	109.5
C10—N3—C11	123.2 (15)	H12A—C12—H12C	109.5
C10—N3—C12	119.1 (14)	H12B—C12—H12C	109.5
C11—N3—C12	117.5 (15)	O10—C10—N3	126.5 (16)
N1—C1—N2	113.5 (13)	O10—C10—H10	116.7
N1—C1—H1	123.2	N3—C10—H10	116.7
N2—C1—H1	123.2	H5W—O3W—H6W	105.9
C7—C2—N1	111.8 (12)	H3W—O2W—H4W	103.7
C7—C2—C3	120.0 (13)	O3—C9—O4	121.1 (12)
N1—C2—C3	128.2 (13)	O3—C9—C4	122.1 (12)
C4—C3—C2	117.7 (11)	O4—C9—C4	116.8 (13)
C4—C3—H3	121.2	C9—O3—Cd1ii	128.7 (8)
C2—C3—H3	121.2	C9—O4—Cd1iv	118.5 (7)
C3—C4—C5	121.6 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2iii	0.84	1.92	2.757 (11)	177
O1W—H2W···O4ii	0.84	1.85	2.649 (12)	159
O2W—H3W···O1W	0.84	2.16	2.888 (9)	145
O2W—H4W···O1	0.84	2.00	2.811 (11)	162
O3W—H5W···O2iii	0.84	2.11	2.810 (12)	140
O3W—H6W···O2Wv	0.84	2.29	2.766 (14)	117
N2—H2···O2Wvi	0.86	2.18	2.970 (16)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2i	0.84	1.92	2.757 (11)	177
O1W—H2W⋯O4ii	0.84	1.85	2.649 (12)	159
O2W—H3W⋯O1W	0.84	2.16	2.888 (9)	145
O2W—H4W⋯O1	0.84	2.00	2.811 (11)	162
O3W—H5W⋯O2i	0.84	2.11	2.810 (12)	140
O3W—H6W⋯O2Wiii	0.84	2.29	2.766 (14)	117
N2—H2⋯O2Wiv	0.86	2.18	2.970 (16)	152

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