catena-Poly[[[bis­(benzoato-κO)copper(II)]-μ-1,1′-(3-oxapentane-1,5-diyl)diimidazole] monohydrate]

In the title compound, {[Cu(C₇H₅O₂)₂(C₁₀H₁₄N₄O)]·H₂O}_n or {[Cu(BA)₂(BIE)]·H₂O}_n, where BA is the benzoate anion and BIE is 2,2′-bis­(imidazolethyl), the Cu^II atom, which lies on an inversion centre, is coordinated in a square-planar geometry by two N atoms from two BIE ligands and two O atoms from two benzoate anions. The ether and water O atoms are located on twofold axes. The Cu^II atoms are linked via BIE ligands to form a one-dimensional chain structure along the c axis. The chains are further connected through hydrogen-bonding inter­actions between the water mol­ecules and the carboxyl­ate O atoms of the BA anions, resulting in a two-dimensional supra­molecular network. The C atom and H atoms of the ethyl chain are disordered over two positions with refined occupancies of 0.583 (12) and 0.417 (12).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.046
• wR factor = 0.123
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C12     ..       7.11 su

Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space-group P2/c    ....      P2/n
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The design and synthesis of coordination polymers has received much attention due to their interesting structures and potential applications in ion exchange and gas storage (Yang, Yue et al., 2006). In this regard, chain structures are particularly interesting (Yang et al., 2007). We selected 2,2'-bis(imidazol)ether (BIE) as a bridging ligand, generating a new chain coordination polymer, {[Cu(BA)₂(BIE)].H₂O}_n, whose structure is reported here.

In the title compound, the copper(II) atom, which lies on an inversion centre, displays a square-planar coordination geometry provided by two nitrogen atoms from two BIE ligands and two oxygen atoms from two distinct benzoate anions (Fig. 1). The Cu—O and Cu—N distances (Cu1—N1 = 1.985 (2) Å, Cu1–O2 = 1.968 (2) Å) are within their normal ranges (Yang, Ma et al., 2006). The copper(II) centers are linked via BIE ligands to form a one-dimensional chain structure along the c axis (Fig. 2). The monodentate BA anions are located on both sides of the chain. The adjacent chains are further connected through hydrogen bonds between BA anions and water molecules (Table 2), thus forming a two-dimensional supramolecular network (Fig. 3). The ether (O3) and water (O1W) oxygen atoms lie on twofold axes. The C11, C12 carbon atom and attached H atoms are disordered over two positions with refined occupancies of 0.583 (12) and 0.417 (12).

Related literature

For related literature, see: Yang et al. (2007); Yang, Ma et al. (2006); Yang, Yue et al. (2006).

S2. Experimental

A mixture of CuCl₂.2H₂O (86.0 mg, 0.5 mmol) and NaOH (40 mg, 1 mmol) in 20 ml water was stirred for 10 min at room temperature, then the Cu(OH)₂ precipitate was filtered. HBA (122.0 mg, 1 mmol) was added to the Cu(OH)₂ suspension in C₂H₅OH/H₂O (1:4 v/v) with constant stirring for 1 h until a blue precipitate was obtained. The solid was filtered off and washed with water, then BIE (103.1 mg, 0.5 mmol) was added with stirring for 1 h to give a blue solution. Blue crystals of the title compound were obtained on slow evaporation of the solvent at room temperature.

S3. Refinement

All H atoms bound to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93–0.97 Å and U_iso = 1.2U_eq(C). The independent water H atom was located in a difference Fourier map and refined with U_iso(H) = 1.5U_eq(O) and with the O—H distance constrained to 0.85 Å.

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. ORTEP view of title compound showing 50% probability ellipsoids. Symmetry code: (i) -x, -y, -z + 1; (ii) -x + 1/2, y, -z + 3/2.
	Fig. 2. View of the one-dimensional polymeric chain of the title compound. H atoms are omitted for clarity.
	Fig. 3. View of the two-dimensional supramolecular network via hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding are omitted for clarity.

catena-Poly[[[bis(benzoato-κO)copper(II)]-µ-1,1'- (3-oxapentane-1,5-diyl)diimidazole] monohydrate]

Crystal data

[Cu(C7H5O2)2(C10H14N4O)]·H2O	F(000) = 550
Mr = 530.04	Dx = 1.493 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 7716 reflections
a = 11.4960 (15) Å	θ = 3.0–27.5°
b = 7.7400 (16) Å	µ = 0.97 mm^−1
c = 13.609 (3) Å	T = 293 K
β = 103.140 (3)°	Block, blue
V = 1179.2 (4) Å^3	0.11 × 0.11 × 0.10 mm
Z = 2

Data collection

Rigaku RAXIS-RAPID diffractometer	2697 independent reflections
Radiation source: rotor target	1980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −14→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.901, Tmax = 0.907	l = −17→17
10769 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 0.8067P] where P = (Fo^2 + 2Fc^2)/3
2697 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.44 e Å^−3
1 restraint	Δρmin = −0.51 e Å^−3

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	Occ. (<1)
Cu1	0.0000	0.0000	0.5000	0.03667 (17)
C1	0.0488 (3)	−0.3199 (5)	0.6225 (3)	0.0655 (10)
H1	0.1290	−0.2915	0.6450	0.079*
C2	−0.1193 (3)	−0.4557 (5)	0.6050 (3)	0.0616 (10)
H2	−0.1777	−0.5356	0.6112	0.074*
C3	−0.1333 (3)	−0.3151 (5)	0.5459 (3)	0.0590 (9)
H3	−0.2051	−0.2808	0.5038	0.071*
C4	0.2271 (2)	−0.0881 (4)	0.5132 (2)	0.0400 (6)
C5	0.3558 (2)	−0.1290 (4)	0.5583 (2)	0.0403 (6)
C6	0.4217 (3)	−0.2260 (5)	0.5036 (2)	0.0508 (8)
H6	0.3858	−0.2661	0.4394	0.061*
C7	0.5408 (3)	−0.2624 (6)	0.5451 (3)	0.0649 (10)
H7	0.5844	−0.3279	0.5087	0.078*
C8	0.5948 (3)	−0.2028 (6)	0.6391 (3)	0.0669 (10)
H8	0.6750	−0.2266	0.6660	0.080*
C9	0.5303 (3)	−0.1074 (5)	0.6939 (3)	0.0620 (10)
H9	0.5670	−0.0660	0.7575	0.074*
C10	0.4102 (3)	−0.0734 (5)	0.6537 (2)	0.0501 (8)
H10	0.3662	−0.0123	0.6917	0.060*
C11	0.0454 (8)	−0.6286 (12)	0.6974 (8)	0.050 (3)	0.417 (12)
H11A	−0.0168	−0.6987	0.7149	0.060*	0.417 (12)
H11B	0.0824	−0.6922	0.6512	0.060*	0.417 (12)
C12	0.1351 (9)	−0.5730 (14)	0.7888 (8)	0.052 (3)	0.417 (12)
H12A	0.1543	−0.6674	0.8366	0.062*	0.417 (12)
H12B	0.1049	−0.4769	0.8214	0.062*	0.417 (12)
C11'	0.0548 (7)	−0.5492 (11)	0.7543 (7)	0.060 (2)	0.583 (12)
H11C	0.0745	−0.4648	0.8082	0.072*	0.583 (12)
H11D	−0.0016	−0.6309	0.7713	0.072*	0.583 (12)
C12'	0.1665 (7)	−0.6430 (10)	0.7439 (7)	0.067 (2)	0.583 (12)
H12C	0.1908	−0.7266	0.7978	0.081*	0.583 (12)
H12D	0.1538	−0.7025	0.6796	0.081*	0.583 (12)
N1	−0.0276 (2)	−0.2293 (3)	0.55599 (18)	0.0416 (6)
N2	−0.0022 (3)	−0.4574 (4)	0.6540 (3)	0.0697 (10)
O1	0.18108 (18)	−0.1261 (3)	0.42329 (15)	0.0494 (5)
O2	0.16920 (18)	−0.0139 (3)	0.57095 (15)	0.0431 (5)
O3	0.2500	−0.5163 (5)	0.7500	0.0835 (14)
O1W	0.2500	−0.2648 (5)	0.2500	0.0689 (10)
H1A	0.263 (5)	−0.193 (4)	0.207 (3)	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0352 (3)	0.0402 (3)	0.0364 (3)	0.0039 (2)	0.0117 (2)	0.0030 (2)
C1	0.0405 (17)	0.071 (2)	0.087 (3)	0.0054 (17)	0.0194 (17)	0.038 (2)
C2	0.054 (2)	0.052 (2)	0.079 (3)	−0.0057 (16)	0.0169 (19)	0.0142 (18)
C3	0.0481 (18)	0.057 (2)	0.067 (2)	−0.0066 (16)	0.0034 (16)	0.0101 (18)
C4	0.0366 (14)	0.0382 (16)	0.0452 (16)	−0.0012 (12)	0.0097 (13)	0.0063 (13)
C5	0.0372 (14)	0.0417 (16)	0.0419 (15)	0.0005 (13)	0.0086 (12)	0.0078 (13)
C6	0.0413 (16)	0.063 (2)	0.0479 (17)	0.0043 (15)	0.0099 (13)	−0.0028 (16)
C7	0.0435 (17)	0.089 (3)	0.065 (2)	0.0157 (19)	0.0173 (17)	0.001 (2)
C8	0.0405 (17)	0.097 (3)	0.060 (2)	0.0116 (19)	0.0038 (16)	0.006 (2)
C9	0.0521 (19)	0.078 (3)	0.0486 (18)	−0.0012 (19)	−0.0027 (16)	−0.0014 (18)
C10	0.0482 (17)	0.0537 (19)	0.0476 (17)	0.0018 (15)	0.0094 (14)	−0.0010 (15)
C11	0.058 (5)	0.043 (5)	0.045 (5)	−0.009 (4)	0.004 (4)	0.002 (4)
C12	0.062 (6)	0.046 (5)	0.044 (5)	0.003 (5)	0.007 (5)	0.011 (4)
C11'	0.063 (4)	0.061 (5)	0.054 (5)	−0.002 (4)	0.007 (4)	0.023 (4)
C12'	0.077 (5)	0.047 (4)	0.067 (5)	0.013 (4)	−0.007 (4)	−0.005 (4)
N1	0.0395 (12)	0.0442 (14)	0.0434 (13)	0.0037 (11)	0.0144 (11)	0.0043 (11)
N2	0.0497 (16)	0.0665 (19)	0.098 (2)	0.0122 (15)	0.0279 (17)	0.0449 (18)
O1	0.0429 (11)	0.0594 (14)	0.0441 (11)	0.0040 (10)	0.0060 (9)	−0.0014 (10)
O2	0.0371 (10)	0.0495 (12)	0.0434 (11)	0.0060 (9)	0.0104 (9)	0.0045 (9)
O3	0.053 (2)	0.058 (2)	0.121 (4)	0.000	−0.019 (2)	0.000
O1W	0.095 (3)	0.063 (2)	0.053 (2)	0.000	0.026 (2)	0.000

Geometric parameters (Å, º)

Cu1—O2	1.968 (2)	C8—H8	0.9300
Cu1—O2^i	1.968 (2)	C9—C10	1.389 (4)
Cu1—N1	1.985 (2)	C9—H9	0.9300
Cu1—N1^i	1.985 (2)	C10—H10	0.9300
C1—N1	1.311 (4)	C11—C12	1.487 (16)
C1—N2	1.333 (4)	C11—N2	1.502 (9)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.341 (5)	C11—H11B	0.9700
C2—N2	1.360 (5)	C12—O3	1.591 (10)
C2—H2	0.9300	C12—H12A	0.9700
C3—N1	1.364 (4)	C12—H12B	0.9700
C3—H3	0.9300	C11'—C12'	1.509 (14)
C4—O1	1.252 (3)	C11'—N2	1.546 (8)
C4—O2	1.276 (3)	C11'—H11C	0.9700
C4—C5	1.501 (4)	C11'—H11D	0.9700
C5—C10	1.376 (4)	C12'—O3	1.362 (8)
C5—C6	1.396 (4)	C12'—H12C	0.9700
C6—C7	1.386 (4)	C12'—H12D	0.9700
C6—H6	0.9300	O3—C12'^ii	1.362 (8)
C7—C8	1.369 (5)	O3—C12^ii	1.591 (10)
C7—H7	0.9300	O1W—H1A	0.85 (4)
C8—C9	1.380 (5)
O2—Cu1—O2^i	180.0	C12—C11—H11B	111.5
O2—Cu1—N1	89.37 (9)	N2—C11—H11B	111.5
O2^i—Cu1—N1	90.63 (9)	H11A—C11—H11B	109.3
O2—Cu1—N1^i	90.63 (9)	C11—C12—O3	105.8 (8)
O2^i—Cu1—N1^i	89.37 (9)	C11—C12—H12A	110.6
N1—Cu1—N1^i	180.0	O3—C12—H12A	110.6
N1—C1—N2	112.0 (3)	C11—C12—H12B	110.6
N1—C1—H1	124.0	O3—C12—H12B	110.6
N2—C1—H1	124.0	H12A—C12—H12B	108.7
C3—C2—N2	105.8 (3)	C12'—C11'—N2	109.7 (7)
C3—C2—H2	127.1	C12'—C11'—H11C	109.7
N2—C2—H2	127.1	N2—C11'—H11C	109.7
C2—C3—N1	110.6 (3)	C12'—C11'—H11D	109.7
C2—C3—H3	124.7	N2—C11'—H11D	109.7
N1—C3—H3	124.7	H11C—C11'—H11D	108.2
O1—C4—O2	122.9 (3)	O3—C12'—C11'	104.5 (7)
O1—C4—C5	120.6 (3)	O3—C12'—C12'^ii	46.1 (4)
O2—C4—C5	116.5 (3)	C11'—C12'—C12'^ii	149.4 (6)
C10—C5—C6	119.1 (3)	O3—C12'—H12C	110.9
C10—C5—C4	121.0 (3)	C11'—C12'—H12C	110.9
C6—C5—C4	120.0 (3)	C12'^ii—C12'—H12C	79.7
C7—C6—C5	119.8 (3)	O3—C12'—H12D	110.9
C7—C6—H6	120.1	C11'—C12'—H12D	110.9
C5—C6—H6	120.1	C12'^ii—C12'—H12D	91.2
C8—C7—C6	120.6 (3)	H12C—C12'—H12D	108.9
C8—C7—H7	119.7	C1—N1—C3	104.5 (3)
C6—C7—H7	119.7	C1—N1—Cu1	127.1 (2)
C7—C8—C9	120.0 (3)	C3—N1—Cu1	127.8 (2)
C7—C8—H8	120.0	C1—N2—C2	107.0 (3)
C9—C8—H8	120.0	C1—N2—C11	133.1 (4)
C8—C9—C10	119.8 (3)	C2—N2—C11	115.7 (4)
C8—C9—H9	120.1	C1—N2—C11'	121.5 (4)
C10—C9—H9	120.1	C2—N2—C11'	127.7 (4)
C5—C10—C9	120.7 (3)	C4—O2—Cu1	108.55 (18)
C5—C10—H10	119.7	C12'^ii—O3—C12'	87.8 (7)
C9—C10—H10	119.7	C12'—O3—C12^ii	114.1 (8)
C12—C11—N2	101.3 (8)	C12'^ii—O3—C12	114.1 (8)
C12—C11—H11A	111.5	C12^ii—O3—C12	148.0 (9)
N2—C11—H11A	111.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1^iii	0.85 (4)	2.08 (5)	2.862 (3)	153 (4)

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