Penta-aqua-(1H-benzimidazole-5,6-di-carboxyl-ato-κN)copper(II) penta-hydrate.

The title compound, [Cu(C(9)H(4)N(2)O(4))(H(2)O)(5)]·5H(2)O, contains one crystallographically independent Cu(II) atom and one 1H-benzimidazole-5,6-dicarboxyl-ate (bdc) ligand, along with five coordinated and five uncoordinated water mol-ecules. The Cu(II) atom is six-coordinated by one N atom from the bdc ligand and five O atoms from water mol-ecules, giving an octa-hedral coordination geometry. Hydrogen bonds link the mononuclear complex and uncoordinated water mol-ecules into a three-dimensional network.

Related literature

For related literature, see: Lemos et al. (2004 ▶); Park et al. (2006 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

[Cu(C9n class="Species">H4N2O4)(H2O)5]·5H2O

M = 447.84

Triclinic,

a = 6.8449 (5) Å

b = 11.4381 (8) Å

c = 12.3549 (9) Å

α = 78.1549 (1)°

β = 78.6224 (1)°

γ = 74.8804 (1)°

V = 903.29 (11) Å3

Z = 2

Mo Kα radiation

μ = 1.28 mm−1

T = 296 (2) K

0.24 × 0.24 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.748, T max = 0.748

4648 measured reflections

3164 independent reflections

2774 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.05

3164 reflections

295 parameters

20 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.54 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017595/kj2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017595/kj2082Isup2.hkl

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

[Cu(C9H4N2O4)(H2O)5]·5H2O	Z = 2
Mr = 447.84	F000 = 466
Triclinic, P1	Dx = 1.647 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.8449 (5) Å	Cell parameters from 2164 reflections
b = 11.4381 (8) Å	θ = 2.7–27.7º
c = 12.3549 (9) Å	µ = 1.28 mm−1
α = 78.1549 (1)º	T = 296 (2) K
β = 78.6224 (1)º	Block, green
γ = 74.8804 (1)º	0.24 × 0.24 × 0.24 mm
V = 903.29 (11) Å3

Bruker SMART CCD area-detector diffractometer	3164 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
T = 296(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −8→7
Tmin = 0.748, Tmax = 0.748	k = −13→9
4648 measured reflections	l = −14→13

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0394P)2 + 1.2855P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3164 reflections	Δρmax = 0.32 e Å−3
295 parameters	Δρmin = −0.53 e Å−3
20 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Cu2	0.40064 (5)	0.90276 (3)	0.25900 (3)	0.01956 (13)
C1	0.5610 (5)	0.7927 (3)	0.0504 (2)	0.0208 (6)
H1B	0.5372	0.8719	0.0100	0.025*
C2	0.5701 (4)	0.6408 (2)	0.1857 (2)	0.0155 (6)
C3	0.5523 (4)	0.5625 (2)	0.2878 (2)	0.0164 (6)
H3A	0.4908	0.5933	0.3535	0.020*
C4	0.6288 (4)	0.4374 (2)	0.2891 (2)	0.0164 (6)
C5	0.7248 (4)	0.3904 (3)	0.1890 (2)	0.0174 (6)
C6	0.7410 (5)	0.4686 (3)	0.0879 (2)	0.0209 (6)
H6A	0.8036	0.4385	0.0220	0.025*
C7	0.6613 (4)	0.5927 (3)	0.0878 (2)	0.0188 (6)
C8	0.6183 (4)	0.3556 (2)	0.4017 (2)	0.0181 (6)
C9	0.7972 (5)	0.2539 (3)	0.1890 (2)	0.0200 (6)
N1	0.6497 (4)	0.6937 (2)	0.0032 (2)	0.0232 (6)
H1A	0.6921	0.6925	−0.0670	0.028*
N2	0.5095 (4)	0.7684 (2)	0.16013 (19)	0.0178 (5)
O1	0.7832 (3)	0.3070 (2)	0.43846 (19)	0.0333 (6)
O1W	0.1811 (3)	0.8182 (2)	0.36057 (18)	0.0231 (5)
H1D	0.206 (6)	0.780 (3)	0.418 (2)	0.035*
H1C	0.145 (6)	0.774 (3)	0.331 (3)	0.035*
O2	0.4460 (3)	0.3461 (2)	0.45410 (18)	0.0296 (5)
O2W	0.2065 (4)	0.9916 (2)	0.14521 (19)	0.0267 (5)
H2B	0.151 (6)	0.950 (3)	0.122 (3)	0.040*
H2A	0.119 (5)	1.055 (3)	0.154 (3)	0.040*
O3	0.6926 (3)	0.18604 (18)	0.25581 (18)	0.0281 (5)
O3W	0.6198 (3)	0.9979 (2)	0.16683 (18)	0.0236 (5)
H3B	0.652 (6)	1.045 (3)	0.196 (3)	0.035*
H3C	0.719 (5)	0.957 (3)	0.139 (3)	0.035*
O4	0.9510 (3)	0.21717 (19)	0.12100 (18)	0.0296 (5)
O4W	0.2824 (5)	1.0432 (2)	0.3484 (2)	0.0410 (7)
H4B	0.255 (7)	1.113 (3)	0.320 (4)	0.061*
H4A	0.275 (7)	1.030 (4)	0.416 (2)	0.061*
O5W	0.6079 (3)	0.8194 (2)	0.36953 (18)	0.0241 (5)
H5B	0.647 (6)	0.873 (3)	0.385 (3)	0.036*
H5A	0.579 (6)	0.775 (3)	0.424 (2)	0.036*
O6W	0.0815 (4)	0.4415 (2)	0.3683 (2)	0.0397 (6)
H6B	−0.005 (6)	0.402 (4)	0.403 (4)	0.060*
H6C	0.164 (6)	0.421 (4)	0.410 (3)	0.060*
O7W	0.2891 (4)	0.2718 (2)	0.2314 (2)	0.0330 (5)
H7A	0.406 (4)	0.257 (4)	0.244 (4)	0.050*
H7B	0.224 (6)	0.331 (3)	0.262 (3)	0.050*
O8W	0.9900 (4)	0.6813 (2)	0.2776 (2)	0.0353 (6)
H8B	0.874 (4)	0.710 (4)	0.303 (3)	0.053*
H8A	1.008 (7)	0.609 (3)	0.303 (4)	0.053*
O9W	−0.0044 (4)	0.8476 (2)	0.0862 (2)	0.0339 (6)
H9B	0.018 (7)	0.825 (4)	0.027 (3)	0.051*
H9A	0.013 (7)	0.789 (3)	0.133 (3)	0.051*
O10W	0.8011 (4)	0.9835 (2)	0.4212 (2)	0.0312 (5)
H10B	0.779 (6)	1.053 (3)	0.387 (3)	0.047*
H10A	0.919 (4)	0.953 (4)	0.402 (3)	0.047*

	U11	U22	U33	U12	U13	U23
Cu2	0.0244 (2)	0.0145 (2)	0.0180 (2)	−0.00297 (14)	−0.00237 (14)	−0.00150 (14)
C1	0.0287 (16)	0.0122 (14)	0.0197 (15)	−0.0042 (12)	−0.0049 (12)	0.0018 (11)
C2	0.0185 (14)	0.0112 (13)	0.0165 (14)	−0.0022 (11)	−0.0039 (11)	−0.0021 (11)
C3	0.0208 (15)	0.0161 (14)	0.0120 (13)	−0.0041 (11)	−0.0004 (11)	−0.0040 (11)
C4	0.0193 (14)	0.0141 (14)	0.0159 (14)	−0.0041 (11)	−0.0056 (11)	0.0005 (11)
C5	0.0193 (14)	0.0140 (14)	0.0183 (14)	−0.0022 (11)	−0.0033 (11)	−0.0031 (11)
C6	0.0280 (16)	0.0184 (15)	0.0141 (14)	−0.0040 (12)	0.0024 (12)	−0.0046 (11)
C7	0.0242 (15)	0.0157 (14)	0.0146 (14)	−0.0038 (12)	−0.0028 (11)	0.0010 (11)
C8	0.0270 (16)	0.0118 (14)	0.0153 (14)	−0.0054 (12)	−0.0039 (12)	0.0000 (11)
C9	0.0253 (16)	0.0148 (14)	0.0203 (15)	−0.0010 (12)	−0.0084 (12)	−0.0037 (12)
N1	0.0372 (15)	0.0161 (13)	0.0117 (12)	−0.0040 (11)	0.0002 (11)	0.0016 (10)
N2	0.0240 (13)	0.0106 (12)	0.0168 (12)	−0.0022 (10)	−0.0031 (10)	−0.0002 (9)
O1	0.0296 (13)	0.0388 (14)	0.0270 (12)	−0.0103 (10)	−0.0113 (10)	0.0145 (10)
O1W	0.0278 (12)	0.0234 (12)	0.0173 (11)	−0.0090 (9)	−0.0051 (9)	0.0038 (9)
O2	0.0263 (12)	0.0315 (13)	0.0239 (12)	−0.0079 (10)	−0.0016 (9)	0.0111 (10)
O2W	0.0290 (13)	0.0182 (12)	0.0315 (12)	0.0036 (9)	−0.0134 (10)	−0.0038 (10)
O3	0.0342 (13)	0.0142 (11)	0.0338 (13)	−0.0069 (9)	−0.0013 (10)	−0.0013 (9)
O3W	0.0270 (12)	0.0193 (11)	0.0253 (12)	−0.0088 (9)	0.0003 (9)	−0.0050 (9)
O4	0.0333 (13)	0.0177 (11)	0.0302 (12)	0.0044 (9)	0.0016 (10)	−0.0061 (9)
O4W	0.0744 (19)	0.0175 (12)	0.0255 (13)	−0.0081 (12)	0.0065 (13)	−0.0079 (11)
O5W	0.0322 (12)	0.0231 (12)	0.0182 (11)	−0.0122 (10)	−0.0075 (9)	0.0053 (9)
O6W	0.0334 (15)	0.0358 (15)	0.0475 (17)	−0.0081 (12)	−0.0107 (12)	0.0035 (12)
O7W	0.0357 (14)	0.0362 (14)	0.0265 (12)	−0.0074 (12)	−0.0041 (11)	−0.0054 (10)
O8W	0.0307 (13)	0.0291 (13)	0.0446 (15)	−0.0055 (11)	−0.0069 (11)	−0.0029 (11)
O9W	0.0407 (14)	0.0334 (14)	0.0280 (13)	−0.0050 (11)	−0.0076 (11)	−0.0080 (11)
O10W	0.0313 (13)	0.0268 (13)	0.0305 (13)	−0.0033 (11)	−0.0033 (11)	0.0007 (10)

Cu2—O4W	2.037 (2)	C9—O4	1.248 (4)
Cu2—O2W	2.055 (2)	C9—O3	1.261 (4)
Cu2—N2	2.055 (2)	N1—H1A	0.8600
Cu2—O1W	2.070 (2)	O1W—H1D	0.78 (2)
Cu2—O5W	2.076 (2)	O1W—H1C	0.80 (2)
Cu2—O3W	2.097 (2)	O2W—H2B	0.80 (3)
C1—N2	1.322 (4)	O2W—H2A	0.82 (3)
C1—N1	1.328 (4)	O3W—H3B	0.81 (2)
C1—H1B	0.9300	O3W—H3C	0.78 (2)
C2—C3	1.393 (4)	O4W—H4B	0.79 (3)
C2—N2	1.396 (3)	O4W—H4A	0.81 (3)
C2—C7	1.397 (4)	O5W—H5B	0.80 (2)
C3—C4	1.387 (4)	O5W—H5A	0.78 (2)
C3—H3A	0.9300	O6W—H6B	0.84 (3)
C4—C5	1.420 (4)	O6W—H6C	0.79 (3)
C4—C8	1.510 (4)	O7W—H7A	0.81 (3)
C5—C6	1.382 (4)	O7W—H7B	0.83 (3)
C5—C9	1.510 (4)	O8W—H8B	0.80 (3)
C6—C7	1.381 (4)	O8W—H8A	0.81 (3)
C6—H6A	0.9300	O9W—H9B	0.81 (3)
C7—N1	1.387 (4)	O9W—H9A	0.79 (3)
C8—O2	1.248 (4)	O10W—H10B	0.81 (3)
C8—O1	1.249 (4)	O10W—H10A	0.80 (3)
O4W—Cu2—O2W	88.82 (10)	C6—C7—C2	122.3 (3)
O4W—Cu2—N2	176.07 (10)	N1—C7—C2	105.0 (2)
O2W—Cu2—N2	87.32 (9)	O2—C8—O1	124.5 (3)
O4W—Cu2—O1W	86.06 (10)	O2—C8—C4	118.2 (2)
O2W—Cu2—O1W	92.49 (9)	O1—C8—C4	117.3 (3)
N2—Cu2—O1W	94.83 (9)	O4—C9—O3	125.0 (3)
O4W—Cu2—O5W	90.71 (11)	O4—C9—C5	117.9 (3)
O2W—Cu2—O5W	176.77 (9)	O3—C9—C5	117.0 (3)
N2—Cu2—O5W	93.11 (9)	C1—N1—C7	107.4 (2)
O1W—Cu2—O5W	90.66 (9)	C1—N1—H1A	126.3
O4W—Cu2—O3W	89.28 (10)	C7—N1—H1A	126.3
O2W—Cu2—O3W	89.14 (9)	C1—N2—C2	104.4 (2)
N2—Cu2—O3W	89.94 (9)	C1—N2—Cu2	122.93 (19)
O1W—Cu2—O3W	175.03 (9)	C2—N2—Cu2	132.25 (19)
O5W—Cu2—O3W	87.67 (9)	Cu2—O1W—H1D	118 (3)
N2—C1—N1	113.8 (2)	Cu2—O1W—H1C	113 (3)
N2—C1—H1B	123.1	H1D—O1W—H1C	106 (4)
N1—C1—H1B	123.1	Cu2—O2W—H2B	117 (3)
C3—C2—N2	130.6 (3)	Cu2—O2W—H2A	123 (3)
C3—C2—C7	120.0 (3)	H2B—O2W—H2A	105 (4)
N2—C2—C7	109.4 (2)	Cu2—O3W—H3B	118 (3)
C4—C3—C2	118.3 (3)	Cu2—O3W—H3C	115 (3)
C4—C3—H3A	120.8	H3B—O3W—H3C	109 (4)
C2—C3—H3A	120.8	Cu2—O4W—H4B	123 (3)
C3—C4—C5	120.9 (3)	Cu2—O4W—H4A	120 (3)
C3—C4—C8	117.1 (2)	H4B—O4W—H4A	116 (5)
C5—C4—C8	121.9 (2)	Cu2—O5W—H5B	107 (3)
C6—C5—C4	120.5 (3)	Cu2—O5W—H5A	122 (3)
C6—C5—C9	118.4 (3)	H5B—O5W—H5A	109 (4)
C4—C5—C9	121.0 (3)	H6B—O6W—H6C	100 (5)
C7—C6—C5	117.9 (3)	H7A—O7W—H7B	107 (4)
C7—C6—H6A	121.0	H8B—O8W—H8A	104 (5)
C5—C6—H6A	121.0	H9B—O9W—H9A	108 (4)
C6—C7—N1	132.7 (3)	H10B—O10W—H10A	107 (4)
N2—C2—C3—C4	−179.4 (3)	C4—C5—C9—O4	−148.5 (3)
C7—C2—C3—C4	0.6 (4)	C6—C5—C9—O3	−141.7 (3)
C2—C3—C4—C5	0.7 (4)	C4—C5—C9—O3	33.8 (4)
C2—C3—C4—C8	176.6 (3)	N2—C1—N1—C7	−0.4 (4)
C3—C4—C5—C6	−1.1 (4)	C6—C7—N1—C1	−178.6 (3)
C8—C4—C5—C6	−176.7 (3)	C2—C7—N1—C1	1.0 (3)
C3—C4—C5—C9	−176.4 (3)	N1—C1—N2—C2	−0.5 (3)
C8—C4—C5—C9	7.9 (4)	N1—C1—N2—Cu2	172.7 (2)
C4—C5—C6—C7	0.1 (4)	C3—C2—N2—C1	−178.9 (3)
C9—C5—C6—C7	175.5 (3)	C7—C2—N2—C1	1.1 (3)
C5—C6—C7—N1	−179.2 (3)	C3—C2—N2—Cu2	8.8 (5)
C5—C6—C7—C2	1.3 (5)	C7—C2—N2—Cu2	−171.1 (2)
C3—C2—C7—C6	−1.6 (5)	O2W—Cu2—N2—C1	47.3 (2)
N2—C2—C7—C6	178.3 (3)	O1W—Cu2—N2—C1	139.6 (2)
C3—C2—C7—N1	178.7 (3)	O5W—Cu2—N2—C1	−129.5 (2)
N2—C2—C7—N1	−1.3 (3)	O3W—Cu2—N2—C1	−41.8 (2)
C3—C4—C8—O2	67.2 (4)	O2W—Cu2—N2—C2	−141.6 (3)
C5—C4—C8—O2	−116.9 (3)	O1W—Cu2—N2—C2	−49.4 (3)
C3—C4—C8—O1	−109.2 (3)	O5W—Cu2—N2—C2	41.6 (3)
C5—C4—C8—O1	66.7 (4)	O3W—Cu2—N2—C2	129.2 (3)
C6—C5—C9—O4	36.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O10W—H10A···O1Wi	0.80 (3)	2.09 (3)	2.855 (3)	160 (4)
O10W—H10B···O3ii	0.81 (3)	2.05 (3)	2.802 (3)	155 (4)
O9W—H9B···O4iii	0.81 (3)	1.94 (3)	2.739 (3)	174 (4)
O7W—H7B···O6W	0.83 (3)	1.95 (3)	2.758 (4)	166 (4)
O7W—H7A···O3	0.81 (3)	1.94 (3)	2.735 (3)	165 (4)
O6W—H6C···O2	0.79 (3)	2.03 (3)	2.773 (3)	156 (5)
O6W—H6B···O1iv	0.84 (3)	1.96 (3)	2.772 (4)	162 (5)
O5W—H5A···O2v	0.78 (2)	1.84 (3)	2.611 (3)	170 (4)
O5W—H5B···O10W	0.80 (2)	2.01 (3)	2.793 (3)	169 (4)
O4W—H4A···O10Wvi	0.81 (3)	1.96 (3)	2.760 (3)	168 (5)
O4W—H4B···O7Wii	0.79 (3)	1.97 (3)	2.723 (4)	160 (5)
O3W—H3C···O9Wi	0.78 (2)	2.05 (3)	2.820 (3)	172 (4)
O3W—H3B···O3ii	0.81 (2)	2.00 (3)	2.800 (3)	170 (4)
O2W—H2A···O4vii	0.82 (3)	1.93 (3)	2.709 (3)	160 (4)
O2W—H2B···O9W	0.80 (3)	1.94 (3)	2.735 (3)	172 (4)
O1W—H1D···O1v	0.78 (2)	1.85 (3)	2.621 (3)	170 (4)
N1—H1A···O7Wiii	0.86	1.97	2.805 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10W—H10A⋯O1Wi	0.80 (3)	2.09 (3)	2.855 (3)	160 (4)
O10W—H10B⋯O3ii	0.81 (3)	2.05 (3)	2.802 (3)	155 (4)
O9W—H9B⋯O4iii	0.81 (3)	1.94 (3)	2.739 (3)	174 (4)
O7W—H7B⋯O6W	0.83 (3)	1.95 (3)	2.758 (4)	166 (4)
O7W—H7A⋯O3	0.81 (3)	1.94 (3)	2.735 (3)	165 (4)
O6W—H6C⋯O2	0.79 (3)	2.03 (3)	2.773 (3)	156 (5)
O6W—H6B⋯O1iv	0.84 (3)	1.96 (3)	2.772 (4)	162 (5)
O5W—H5A⋯O2v	0.78 (2)	1.84 (3)	2.611 (3)	170 (4)
O5W—H5B⋯O10W	0.80 (2)	2.01 (3)	2.793 (3)	169 (4)
O4W—H4A⋯O10Wvi	0.81 (3)	1.96 (3)	2.760 (3)	168 (5)
O4W—H4B⋯O7Wii	0.79 (3)	1.97 (3)	2.723 (4)	160 (5)
O3W—H3C⋯O9Wi	0.78 (2)	2.05 (3)	2.820 (3)	172 (4)
O3W—H3B⋯O3ii	0.81 (2)	2.00 (3)	2.800 (3)	170 (4)
O2W—H2A⋯O4vii	0.82 (3)	1.93 (3)	2.709 (3)	160 (4)
O2W—H2B⋯O9W	0.80 (3)	1.94 (3)	2.735 (3)	172 (4)
O1W—H1D⋯O1v	0.78 (2)	1.85 (3)	2.621 (3)	170 (4)
N1—H1A⋯O7Wiii	0.86	1.97	2.805 (3)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .