catena-Poly­[[aqua­bis(1H-imidazole-κN³)copper(II)]-μ-benzene-1,4-dioxy­acetato-κ²O:O′]

In the title coordination polymer, also called catena-poly­[[aqua­bis(1H-imidazole-κN³)copper(II)]-μ-phenyl­ene­dioxy­diacetato-κ²O:O′], [Cu(1,4-BDOA)(C₃H₄N₂)₂(H₂O)]_n (where 1,4-BDOA²⁻ is benzene-1,4-dioxy­acetate, C₁₀H₈O₆), the Cu^II atom is five-coordinate involving two O atoms of the 1,4-BDOA ligand, two N atoms of imidazole ligands and one water mol­ecule, displaying a distorted square-pyramidal coordination geometry. The Cu^II atoms are bridged by carboxyl­ate groups, forming a one-dimensional zigzag chain. The adjacent Cu...Cu distance is 12.656 (5) Å. Furthermore, such chains are linked by hydrogen-bond interactions, resulting in a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.109
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  O3      ..       2.65 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

'Catena-poly[aquabis(1H-imidazole-KN³)copper(II)-µ-benzene- phenylenedioxydiacetato-κ²O,O']'

Crystal data

[Cu(C10H8O6)(C3H4N2)2(H2O)]	F(000) = 908
Mr = 441.89	Dx = 1.606 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10508 reflections
a = 16.699 (3) Å	θ = 3.2–27.5°
b = 6.0327 (12) Å	µ = 1.24 mm^−1
c = 18.977 (4) Å	T = 293 K
β = 107.06 (3)°	Prism, blue
V = 1827.6 (7) Å^3	0.39 × 0.25 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4153 independent reflections
Radiation source: fine-focus sealed tube	3177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −21→21
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −7→7
Tmin = 0.643, Tmax = 0.807	l = −24→24
11517 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.7112P] where P = (Fo^2 + 2Fc^2)/3
4153 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.42 e Å^−3
5 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.63669 (2)	0.81765 (6)	0.372445 (19)	0.02824 (12)
N1	0.63381 (17)	0.8530 (5)	0.47578 (14)	0.0365 (6)
N2	0.6012 (2)	0.8028 (6)	0.57825 (15)	0.0477 (8)
N3	0.64017 (15)	0.7450 (4)	0.27090 (13)	0.0309 (6)
N4	0.66744 (19)	0.5956 (5)	0.17547 (15)	0.0407 (7)
O1	0.51205 (13)	0.8041 (4)	0.33480 (12)	0.0370 (5)
O2	0.50512 (14)	0.4429 (4)	0.35913 (13)	0.0412 (6)
O3	0.34521 (14)	0.4211 (4)	0.26329 (12)	0.0389 (5)
O4	0.42301 (14)	0.0426 (4)	0.02567 (12)	0.0409 (6)
O5	0.76199 (13)	0.8028 (4)	0.40997 (11)	0.0362 (5)
O6	0.75911 (15)	0.4467 (4)	0.44132 (14)	0.0477 (6)
O1W	0.63894 (14)	1.1822 (4)	0.34993 (13)	0.0393 (5)
C1	0.5808 (2)	0.7593 (7)	0.50618 (18)	0.0498 (10)
C2	0.6716 (2)	0.9278 (6)	0.59623 (19)	0.0447 (9)
C3	0.6911 (2)	0.9615 (6)	0.53256 (19)	0.0423 (8)
C4	0.5926 (2)	0.8475 (6)	0.20746 (17)	0.0385 (8)
C5	0.6091 (2)	0.7551 (6)	0.14872 (17)	0.0397 (8)
C6	0.6849 (2)	0.5936 (6)	0.24909 (18)	0.0374 (7)
C7	0.47468 (19)	0.6206 (5)	0.33111 (16)	0.0308 (7)
C8	0.3812 (2)	0.6311 (5)	0.28965 (19)	0.0383 (8)
C9	0.36731 (18)	0.3315 (5)	0.20443 (16)	0.0313 (7)
C10	0.4250 (2)	0.4251 (6)	0.17340 (18)	0.0365 (7)
C11	0.44057 (19)	0.3224 (6)	0.11384 (16)	0.0356 (7)
C12	0.40035 (18)	0.1291 (5)	0.08443 (16)	0.0303 (7)
C13	0.34308 (19)	0.0348 (6)	0.11569 (16)	0.0336 (7)
C14	0.32729 (18)	0.1363 (5)	0.17548 (17)	0.0336 (7)
C15	0.38411 (19)	−0.1563 (6)	−0.00764 (18)	0.0375 (7)
C16	0.79387 (19)	0.6261 (5)	0.44384 (16)	0.0311 (7)
H1W1	0.5939 (11)	1.247 (5)	0.350 (2)	0.059*
H1W2	0.6806 (12)	1.246 (5)	0.3794 (17)	0.059*
H1	0.5351	0.6739	0.4807	0.060*
H2	0.7008	0.9799	0.6428	0.054*
H3	0.7361	1.0449	0.5279	0.051*
H4	0.5549	0.9626	0.2056	0.046*
H5	0.5852	0.7930	0.0995	0.048*
H6	0.7231	0.4988	0.2804	0.045*
H8B	0.3516	0.6926	0.3221	0.046*
H8A	0.3730	0.7310	0.2481	0.046*
H10	0.4527	0.5553	0.1925	0.044*
H11	0.4792	0.3850	0.0930	0.043*
H13	0.3156	−0.0957	0.0966	0.040*
H14	0.2892	0.0726	0.1967	0.040*
H15A	0.3846	−0.2625	0.0309	0.045*
H15B	0.4170	−0.2182	−0.0374	0.045*
H17	0.572 (2)	0.749 (7)	0.6069 (19)	0.072*
H18	0.688 (2)	0.495 (5)	0.1508 (19)	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0303 (2)	0.0320 (2)	0.02456 (18)	−0.00087 (17)	0.01142 (13)	0.00066 (17)
N1	0.0411 (16)	0.0410 (16)	0.0301 (13)	−0.0076 (12)	0.0147 (12)	−0.0038 (12)
N2	0.0582 (19)	0.061 (2)	0.0309 (14)	−0.0131 (16)	0.0235 (13)	−0.0010 (15)
N3	0.0342 (14)	0.0324 (14)	0.0276 (12)	0.0031 (11)	0.0114 (11)	0.0014 (11)
N4	0.0481 (17)	0.0457 (17)	0.0339 (15)	−0.0028 (14)	0.0209 (13)	−0.0098 (13)
O1	0.0335 (12)	0.0421 (13)	0.0364 (12)	−0.0045 (10)	0.0117 (9)	−0.0031 (11)
O2	0.0358 (13)	0.0451 (14)	0.0422 (13)	0.0027 (11)	0.0105 (10)	0.0038 (11)
O3	0.0327 (12)	0.0479 (14)	0.0391 (12)	−0.0073 (10)	0.0151 (10)	−0.0099 (11)
O4	0.0356 (13)	0.0537 (15)	0.0358 (12)	−0.0101 (11)	0.0141 (10)	−0.0132 (11)
O5	0.0347 (12)	0.0444 (14)	0.0312 (11)	0.0042 (10)	0.0127 (9)	0.0104 (11)
O6	0.0452 (14)	0.0422 (15)	0.0493 (15)	−0.0099 (12)	0.0037 (11)	−0.0022 (12)
O1W	0.0372 (12)	0.0297 (12)	0.0511 (14)	−0.0013 (10)	0.0133 (11)	−0.0037 (11)
C1	0.055 (2)	0.066 (3)	0.0315 (17)	−0.0239 (19)	0.0181 (16)	−0.0038 (17)
C2	0.052 (2)	0.052 (2)	0.0319 (17)	−0.0062 (18)	0.0145 (16)	−0.0127 (16)
C3	0.0435 (19)	0.044 (2)	0.0433 (19)	−0.0104 (16)	0.0185 (16)	−0.0101 (16)
C4	0.0390 (18)	0.042 (2)	0.0336 (16)	0.0021 (15)	0.0084 (14)	0.0058 (15)
C5	0.0440 (19)	0.051 (2)	0.0261 (15)	−0.0080 (16)	0.0128 (14)	0.0031 (15)
C6	0.0429 (19)	0.0381 (18)	0.0339 (17)	0.0074 (15)	0.0154 (14)	0.0001 (15)
C7	0.0291 (16)	0.0420 (19)	0.0253 (14)	0.0033 (13)	0.0142 (12)	−0.0041 (13)
C8	0.0320 (17)	0.0371 (19)	0.0453 (19)	0.0028 (13)	0.0104 (14)	−0.0097 (15)
C9	0.0270 (15)	0.0383 (17)	0.0281 (14)	0.0010 (13)	0.0072 (12)	−0.0004 (14)
C10	0.0364 (18)	0.0374 (18)	0.0360 (17)	−0.0115 (14)	0.0112 (14)	−0.0046 (15)
C11	0.0332 (16)	0.0423 (18)	0.0332 (16)	−0.0087 (15)	0.0129 (13)	0.0021 (15)
C12	0.0253 (15)	0.0371 (18)	0.0270 (14)	0.0012 (12)	0.0054 (12)	0.0012 (13)
C13	0.0309 (17)	0.0367 (18)	0.0314 (17)	−0.0063 (13)	0.0066 (13)	−0.0027 (14)
C14	0.0266 (16)	0.0372 (19)	0.0380 (17)	−0.0019 (13)	0.0112 (13)	0.0081 (14)
C15	0.0332 (17)	0.043 (2)	0.0350 (16)	0.0009 (15)	0.0077 (13)	−0.0064 (15)
C16	0.0309 (16)	0.0410 (19)	0.0235 (14)	−0.0001 (13)	0.0112 (12)	−0.0015 (13)

Geometric parameters (Å, º)

Cu1—N1	1.987 (3)	C1—H1	0.9300
Cu1—N3	1.994 (2)	C2—C3	1.355 (5)
Cu1—O1	1.994 (2)	C2—H2	0.9300
Cu1—O5	2.005 (2)	C3—H3	0.9300
Cu1—O1W	2.243 (2)	C4—C5	1.345 (5)
O1—C7	1.263 (4)	C4—H4	0.9300
O2—C7	1.237 (4)	C5—H5	0.9300
O5—C16	1.278 (4)	C6—H6	0.9300
O6—C16	1.222 (4)	C7—C8	1.530 (4)
N1—C1	1.317 (4)	C8—H8A	0.9700
N1—C3	1.378 (4)	C8—H8B	0.9700
N2—C1	1.335 (4)	C9—C10	1.388 (4)
N2—C2	1.354 (5)	C9—C14	1.385 (4)
N2—H17	0.89 (4)	C10—C11	1.379 (4)
N3—C4	1.379 (4)	C10—H10	0.9300
N3—C6	1.321 (4)	C11—C12	1.379 (4)
N4—C5	1.358 (5)	C11—H11	0.9300
N4—C6	1.341 (4)	C12—C13	1.387 (4)
N4—H18	0.89 (3)	C13—C14	1.381 (4)
O3—C9	1.385 (4)	C13—H13	0.9300
O3—C8	1.428 (4)	C14—H14	0.9300
O4—C12	1.381 (4)	C15—C16^i	1.529 (4)
O4—C15	1.421 (4)	C15—H15A	0.9700
O1W—H1W1	0.85 (3)	C15—H15B	0.9700
O1W—H1W2	0.85 (3)	C16—C15^ii	1.529 (4)
N1—Cu1—N3	173.5 (1)	C2—C3—N1	109.5 (3)
N1—Cu1—O1	91.9 (1)	C2—C3—H3	125.3
N1—Cu1—O5	88.8 (1)	C3—N1—Cu1	127.6 (2)
N1—Cu1—O1W	95.1 (1)	C3—C2—H2	127.0
N3—Cu1—O1	88.2 (1)	C4—N3—Cu1	124.9 (2)
N3—Cu1—O5	90.6 (1)	C4—C5—N4	106.4 (3)
N3—Cu1—O1W	91.4 (1)	C4—C5—H5	126.8
O1—Cu1—O5	175.1 (1)	C5—N4—H18	129 (3)
O1—Cu1—O1W	92.63 (9)	C5—C4—N3	109.4 (3)
O5—Cu1—O1W	92.14 (9)	C5—C4—H4	125.3
Cu1—O1W—H1W1	113 (3)	C6—N3—C4	105.7 (3)
Cu1—O1W—H1W2	112 (3)	C6—N3—Cu1	129.4 (2)
N1—C1—N2	111.2 (3)	C6—N4—C5	108.0 (3)
N1—C1—H1	124.4	C6—N4—H18	123 (3)
N1—C3—H3	125.3	C7—O1—Cu1	120.2 (2)
N2—C1—H1	124.4	C7—C8—H8A	108.8
N2—C2—C3	106.0 (3)	C7—C8—H8B	108.8
N2—C2—H2	127.0	C9—O3—C8	116.4 (2)
N3—C4—H4	125.3	C9—C10—H10	120.4
N3—C6—N4	110.5 (3)	C9—C14—H14	119.4
N3—C6—H6	124.8	C10—C11—H11	119.2
N4—C5—H5	126.8	C11—C10—C9	119.1 (3)
N4—C6—H6	124.8	C11—C10—H10	120.4
O1—C7—C8	113.9 (3)	C11—C12—O4	115.5 (3)
O2—C7—O1	127.0 (3)	C11—C12—C13	119.3 (3)
O2—C7—C8	119.0 (3)	C12—O4—C15	118.7 (2)
O3—C8—C7	113.8 (3)	C12—C11—C10	121.7 (3)
O3—C8—H8A	108.8	C12—C11—H11	119.2
O3—C8—H8B	108.8	C12—C13—H13	120.3
O3—C9—C10	124.5 (3)	C13—C14—C9	121.1 (3)
O4—C12—C13	125.2 (3)	C13—C14—H14	119.4
O4—C15—C16^i	114.1 (3)	C14—C9—O3	116.1 (3)
O4—C15—H15A	108.7	C14—C9—C10	119.4 (3)
O4—C15—H15B	108.7	C14—C13—C12	119.4 (3)
O5—C16—C15^ii	113.3 (3)	C14—C13—H13	120.3
O6—C16—O5	126.6 (3)	C16—O5—Cu1	117.0 (2)
O6—C16—C15^ii	120.1 (3)	C16^i—C15—H15A	108.7
C1—N1—Cu1	126.9 (2)	C16^i—C15—H15B	108.7
C1—N1—C3	105.2 (3)	H1W1—O1W—H1W2	110 (2)
C1—N2—C2	108.0 (3)	H8B—C8—H8A	107.7
C1—N2—H17	122 (3)	H15A—C15—H15B	107.6
C2—N2—H17	130 (3)
Cu1—N1—C1—N2	174.4 (3)	O1W—Cu1—N1—C1	129.0 (3)
Cu1—N1—C3—C2	−173.4 (2)	O1W—Cu1—N1—C3	−58.0 (3)
Cu1—N3—C4—C5	−178.7 (2)	O1W—Cu1—N3—C4	−44.7 (3)
Cu1—N3—C6—N4	178.7 (2)	O1W—Cu1—N3—C6	136.5 (3)
Cu1—O1—C7—O2	12.3 (4)	O1W—Cu1—O1—C7	176.3 (2)
Cu1—O1—C7—C8	−170.45 (19)	O1W—Cu1—O5—C16	167.4 (2)
Cu1—O5—C16—O6	18.5 (4)	C1—N1—C3—C2	0.8 (4)
Cu1—O5—C16—C15^ii	−160.3 (2)	C1—N2—C2—C3	1.5 (5)
N1—Cu1—O1—C7	−88.5 (2)	C2—N2—C1—N1	−1.1 (5)
N1—Cu1—O5—C16	72.3 (2)	C3—N1—C1—N2	0.2 (4)
N2—C2—C3—N1	−1.4 (4)	C4—N3—C6—N4	−0.3 (4)
N3—Cu1—O1—C7	84.9 (2)	C5—N4—C6—N3	0.0 (4)
N3—Cu1—O5—C16	−101.1 (2)	C6—N3—C4—C5	0.4 (4)
N3—C4—C5—N4	−0.4 (4)	C6—N4—C5—C4	0.2 (4)
O1—Cu1—N1—C1	36.2 (3)	C8—O3—C9—C10	4.1 (4)
O1—Cu1—N1—C3	−150.8 (3)	C8—O3—C9—C14	−175.2 (3)
O1—Cu1—N3—C4	47.9 (3)	C9—O3—C8—C7	−71.9 (4)
O1—Cu1—N3—C6	−131.0 (3)	C9—C10—C11—C12	0.0 (5)
O1—C7—C8—O3	159.6 (3)	C10—C9—C14—C13	−0.8 (5)
O2—C7—C8—O3	−22.9 (4)	C10—C11—C12—O4	−179.0 (3)
O3—C9—C10—C11	−178.7 (3)	C10—C11—C12—C13	−0.4 (5)
O3—C9—C14—C13	178.6 (3)	C11—C12—C13—C14	0.2 (5)
O4—C12—C13—C14	178.7 (3)	C12—O4—C15—C16^i	74.8 (3)
O5—Cu1—N1—C1	−138.9 (3)	C12—C13—C14—C9	0.4 (5)
O5—Cu1—N1—C3	34.0 (3)	C14—C9—C10—C11	0.6 (5)
O5—Cu1—N3—C4	−136.9 (3)	C15—O4—C12—C11	−179.9 (3)
O5—Cu1—N3—C6	44.3 (3)	C15—O4—C12—C13	1.6 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H17···O2^iii	0.89 (4)	1.98 (4)	2.829 (4)	160 (4)
N2—H17···O3^iii	0.89 (4)	2.65 (4)	3.177 (4)	118 (3)
N4—H18···O5^iv	0.89 (3)	1.98 (3)	2.874 (3)	173 (4)
O1W—H1W1···O2^v	0.85 (3)	1.94 (3)	2.780 (3)	169 (3)
O1W—H1W2···O6^v	0.85 (3)	1.91 (3)	2.745 (3)	167 (3)

Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, y−1/2, −z+1/2; (v) x, y+1, z.