Poly­[[(1H-benz­imidazole-κN³)copper(II)]-μ₃-oxy­diacetato]

In the title compound, [Cu(C₄H₄O₅)(C₇H₆N₂)]_n, three oxydi­acetate (ODA) dianions and one benz­imidazole mol­ecule coordinate to the Cu^II atom, resulting in an enlongated octahedral coordination geometry. Each ODA links three Cu atoms, chelating one and bridging two, forming a three-dimensional polymeric complex.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.052
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2655
           Count of symmetry unique reflns         1554
           Completeness (_total/calc)            170.85%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1101
           Fraction of Friedel pairs measured     0.708
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C11H10CuN2O5	F(000) = 636
Mr = 313.75	Dx = 1.801 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10407 reflections
a = 7.2693 (3) Å	θ = 2.8–25.0°
b = 9.5506 (3) Å	µ = 1.91 mm^−1
c = 16.6714 (4) Å	T = 295 K
V = 1157.43 (7) Å^3	Prism, green
Z = 4	0.33 × 0.22 × 0.18 mm

Data collection

Rigaku RAXIS-RAPID diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	2576 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −9→9
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	k = −12→12
Tmin = 0.53, Tmax = 0.71	l = −21→21
11325 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.052	w = 1/[σ^2(Fo^2) + (0.0292P)^2 + 0.3325P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2655 reflections	Δρmax = 0.28 e Å^−3
172 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1101 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.020 (10)

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
Cu	0.44856 (3)	0.20067 (2)	0.361337 (14)	0.02405 (7)
O1	0.59222 (18)	0.10512 (14)	0.44360 (8)	0.0267 (3)
O2	0.8189 (2)	0.14035 (16)	0.53158 (9)	0.0387 (4)
O3	0.66327 (16)	0.32845 (12)	0.36298 (8)	0.0234 (2)
O4	0.40225 (18)	0.55524 (16)	0.23999 (9)	0.0336 (3)
O5	0.35658 (19)	0.33835 (15)	0.28439 (8)	0.0302 (3)
N1	−0.0553 (3)	0.02671 (18)	0.32313 (10)	0.0331 (4)
H1	−0.1653	0.0347	0.3047	0.040*
N3	0.2293 (2)	0.08373 (16)	0.35638 (11)	0.0252 (3)
C2	0.0713 (3)	0.1265 (2)	0.32466 (11)	0.0288 (4)
H2	0.0517	0.2168	0.3056	0.035*
C4	0.3180 (3)	−0.1538 (2)	0.41269 (14)	0.0382 (5)
H4	0.4381	−0.1307	0.4267	0.046*
C5	0.2478 (4)	−0.2857 (3)	0.42643 (16)	0.0464 (6)
H5	0.3215	−0.3528	0.4509	0.056*
C6	0.0674 (4)	−0.3208 (3)	0.40428 (15)	0.0508 (6)
H6	0.0260	−0.4116	0.4133	0.061*
C7	−0.0499 (4)	−0.2260 (2)	0.36977 (14)	0.0442 (5)
H7	−0.1700	−0.2496	0.3561	0.053*
C8	0.0204 (3)	−0.0921 (2)	0.35630 (13)	0.0302 (4)
C9	0.2010 (3)	−0.0571 (2)	0.37692 (11)	0.0272 (4)
C10	0.7222 (3)	0.17672 (19)	0.47447 (11)	0.0249 (4)
C11	0.7565 (3)	0.3219 (2)	0.43867 (11)	0.0284 (4)
H11A	0.7098	0.3938	0.4744	0.034*
H11B	0.8873	0.3370	0.4312	0.034*
C12	0.6167 (3)	0.4652 (2)	0.33349 (13)	0.0303 (4)
H12A	0.7179	0.5030	0.3023	0.036*
H12B	0.5928	0.5280	0.3780	0.036*
C13	0.4456 (3)	0.4521 (2)	0.28115 (11)	0.0255 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.02068 (10)	0.02309 (10)	0.02837 (11)	−0.00467 (9)	−0.00579 (9)	0.00558 (10)
O1	0.0265 (7)	0.0229 (6)	0.0308 (7)	−0.0018 (5)	−0.0051 (5)	0.0039 (5)
O2	0.0487 (9)	0.0311 (8)	0.0363 (8)	−0.0053 (7)	−0.0218 (7)	0.0101 (6)
O3	0.0234 (5)	0.0243 (6)	0.0227 (5)	−0.0036 (4)	−0.0057 (5)	0.0038 (6)
O4	0.0285 (7)	0.0323 (7)	0.0401 (8)	−0.0013 (6)	−0.0061 (6)	0.0155 (7)
O5	0.0270 (6)	0.0301 (7)	0.0334 (7)	−0.0056 (6)	−0.0087 (6)	0.0081 (6)
N1	0.0226 (7)	0.0383 (10)	0.0383 (9)	−0.0052 (8)	−0.0049 (8)	−0.0008 (7)
N3	0.0222 (7)	0.0245 (7)	0.0290 (8)	−0.0030 (6)	−0.0017 (7)	−0.0006 (7)
C2	0.0252 (9)	0.0294 (10)	0.0319 (9)	−0.0021 (8)	−0.0007 (8)	0.0001 (8)
C4	0.0394 (11)	0.0316 (10)	0.0434 (12)	0.0003 (9)	−0.0045 (10)	0.0033 (10)
C5	0.0607 (14)	0.0294 (12)	0.0490 (13)	0.0017 (12)	−0.0031 (12)	0.0078 (11)
C6	0.0722 (16)	0.0302 (12)	0.0499 (13)	−0.0192 (12)	0.0034 (14)	0.0039 (10)
C7	0.0483 (12)	0.0416 (12)	0.0429 (12)	−0.0230 (11)	−0.0006 (12)	0.0005 (10)
C8	0.0299 (9)	0.0324 (10)	0.0282 (9)	−0.0080 (7)	0.0003 (8)	−0.0014 (8)
C9	0.0299 (9)	0.0245 (9)	0.0271 (10)	−0.0039 (7)	0.0023 (7)	−0.0017 (7)
C10	0.0257 (8)	0.0245 (10)	0.0245 (8)	0.0011 (7)	−0.0022 (7)	0.0017 (7)
C11	0.0312 (9)	0.0281 (11)	0.0258 (9)	−0.0058 (8)	−0.0110 (7)	0.0061 (8)
C12	0.0312 (9)	0.0246 (9)	0.0349 (10)	−0.0072 (7)	−0.0101 (8)	0.0108 (8)
C13	0.0217 (8)	0.0294 (9)	0.0254 (8)	−0.0010 (8)	−0.0002 (8)	0.0052 (7)

Geometric parameters (Å, º)

Cu—O1	1.9504 (13)	C2—H2	0.9300
Cu—O2^i	2.5263 (15)	C4—C5	1.378 (3)
Cu—O3	1.9814 (12)	C4—C9	1.390 (3)
Cu—O4^ii	2.4410 (14)	C4—H4	0.9300
Cu—O5	1.9549 (14)	C5—C6	1.403 (4)
Cu—N3	1.9478 (15)	C5—H5	0.9300
O1—C10	1.275 (2)	C6—C7	1.371 (4)
O2—C10	1.233 (2)	C6—H6	0.9300
O3—C11	1.434 (2)	C7—C8	1.395 (3)
O3—C12	1.436 (2)	C7—H7	0.9300
O4—C13	1.241 (2)	C8—C9	1.398 (3)
O5—C13	1.266 (2)	C10—C11	1.530 (3)
N1—C2	1.325 (3)	C11—H11A	0.9700
N1—C8	1.377 (3)	C11—H11B	0.9700
N1—H1	0.8600	C12—C13	1.524 (3)
N3—C2	1.329 (3)	C12—H12A	0.9700
N3—C9	1.403 (2)	C12—H12B	0.9700
O1—Cu—O3	81.76 (5)	C5—C6—H6	118.9
O1—Cu—O5	163.58 (6)	C6—C7—C8	116.4 (2)
O2^i—Cu—O4^ii	175.46 (5)	C6—C7—H7	121.8
O3—Cu—O5	82.20 (5)	C8—C7—H7	121.8
N3—Cu—O1	101.52 (6)	N1—C8—C7	132.3 (2)
N3—Cu—O3	176.58 (6)	N1—C8—C9	106.08 (16)
N3—Cu—O5	94.47 (6)	C7—C8—C9	121.6 (2)
C10—O1—Cu	115.45 (12)	C4—C9—C8	121.42 (19)
C11—O3—C12	116.90 (14)	C4—C9—N3	130.69 (19)
C11—O3—Cu	110.96 (10)	C8—C9—N3	107.88 (17)
C12—O3—Cu	111.69 (10)	O2—C10—O1	125.65 (18)
C13—O5—Cu	115.50 (12)	O2—C10—C11	117.62 (16)
C2—N1—C8	107.91 (17)	O1—C10—C11	116.71 (16)
C2—N1—H1	126.0	O3—C11—C10	107.80 (14)
C8—N1—H1	126.0	O3—C11—H11A	110.1
C2—N3—C9	105.35 (15)	C10—C11—H11A	110.1
C2—N3—Cu	123.24 (13)	O3—C11—H11B	110.1
C9—N3—Cu	131.25 (13)	C10—C11—H11B	110.1
N1—C2—N3	112.78 (18)	H11A—C11—H11B	108.5
N1—C2—H2	123.6	O3—C12—C13	108.30 (15)
N3—C2—H2	123.6	O3—C12—H12A	110.0
C5—C4—C9	116.9 (2)	C13—C12—H12A	110.0
C5—C4—H4	121.6	O3—C12—H12B	110.0
C9—C4—H4	121.6	C13—C12—H12B	110.0
C4—C5—C6	121.4 (2)	H12A—C12—H12B	108.4
C4—C5—H5	119.3	O4—C13—O5	125.07 (18)
C6—C5—H5	119.3	O4—C13—C12	117.33 (17)
C7—C6—C5	122.3 (2)	O5—C13—C12	117.58 (16)
C7—C6—H6	118.9

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^iii	0.86	1.89	2.746 (3)	177

Symmetry code: (iii) −x, y−1/2, −z+1/2.