catena-Poly­[[(1,10-phenanthroline-κ²N,N′)copper(II)]-μ-4-carboxy­imidazole-5-carboxyl­ato(2–)-κ⁴N,O:N′,O′]

In the title coordination polymer, [Cu(HIDC)(1,10-phen)]_n (HIDC²⁻ is the 4-carboxy­imidazole-5-carboxyl­ate dianion, C₅H₂N₂O₄²⁻, and 1,10-phen is 1,10-phenanthroline, C₁₂H₈N₂), the Cu^II atom shows a distorted octahedral coordination configuration, defined by two N atoms from a terminal 1,10-phen mol­ecule, two N atoms and two O atoms from two individual HIDC²⁻ groups. Adjacent Cu^II atoms are bridged by HIDC²⁻ groups, forming a one-dimensional chain structure. The Cu...Cu separation within the polymer is 6.132 (4) Å. The chains are linked into a two-dimensional supramolecular network via π–π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.055
• wR factor = 0.123
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

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Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 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[[(1,10-phenanthroline-κ²N,N')copper(II)]-µ- 4-carboxyimidazole-5-carboxylato(2-)-κ⁴N,O:N,O']

Crystal data

[Cu(C5H2N2O4)(C12H8N2)]	F(000) = 804
Mr = 397.84	Dx = 1.844 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12710 reflections
a = 10.360 (2) Å	θ = 3.2–27.5°
b = 9.6427 (19) Å	µ = 1.56 mm^−1
c = 14.352 (3) Å	T = 293 K
β = 91.36 (3)°	Prism, blue
V = 1433.3 (5) Å^3	0.24 × 0.18 × 0.10 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3265 independent reflections
Radiation source: fine-focus sealed tube	2385 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −13→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.706, Tmax = 0.859	l = −18→15
13223 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 0.8363P] where P = (Fo^2 + 2Fc^2)/3
3265 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.51 e Å^−3
1 restraint	Δρmin = −0.56 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.33050 (5)	0.58475 (6)	0.19750 (4)	0.02694 (17)
N1	0.1711 (3)	0.6816 (4)	0.1433 (3)	0.0301 (9)
N2	0.2080 (3)	0.4156 (4)	0.1792 (2)	0.0295 (8)
N3	0.4589 (3)	0.4557 (4)	0.2585 (2)	0.0233 (8)
N4	0.5666 (3)	0.2622 (4)	0.2957 (3)	0.0272 (8)
O1	0.2766 (3)	0.5963 (3)	0.3578 (2)	0.0378 (8)
O2	0.3210 (3)	0.4742 (4)	0.4869 (2)	0.0376 (8)
O3	0.4476 (3)	0.2638 (4)	0.5300 (2)	0.0448 (9)
O4	0.5852 (3)	0.1214 (4)	0.4631 (3)	0.0452 (9)
C1	0.1579 (5)	0.8132 (5)	0.1195 (4)	0.0388 (12)
C2	0.0414 (5)	0.8672 (6)	0.0841 (4)	0.0472 (14)
C3	−0.0634 (5)	0.7830 (6)	0.0719 (4)	0.0452 (13)
C4	−0.0533 (4)	0.6429 (6)	0.0940 (3)	0.0347 (11)
C5	−0.1564 (4)	0.5421 (6)	0.0824 (3)	0.0434 (14)
C6	−0.1392 (4)	0.4088 (6)	0.1053 (3)	0.0417 (12)
C7	−0.0156 (4)	0.3587 (5)	0.1406 (3)	0.0340 (11)
C8	0.0114 (5)	0.2204 (6)	0.1601 (3)	0.0402 (12)
C9	0.1331 (4)	0.1825 (5)	0.1885 (4)	0.0393 (12)
C10	0.2290 (4)	0.2829 (5)	0.1960 (3)	0.0344 (11)
C11	0.0871 (4)	0.4550 (5)	0.1516 (3)	0.0294 (10)
C12	0.0678 (4)	0.5957 (5)	0.1302 (3)	0.0292 (10)
C13	0.5397 (4)	0.3559 (5)	0.2296 (3)	0.0284 (10)
C14	0.3380 (4)	0.5056 (5)	0.4018 (3)	0.0270 (10)
C15	0.4334 (4)	0.4238 (5)	0.3493 (3)	0.0247 (9)
C16	0.5003 (4)	0.3034 (4)	0.3725 (3)	0.0238 (9)
C17	0.5135 (4)	0.2227 (5)	0.4592 (3)	0.0346 (11)
H1	0.2286	0.8720	0.1266	0.047*
H2	0.0354	0.9608	0.0687	0.057*
H3	−0.1412	0.8190	0.0490	0.054*
H5	−0.2362	0.5709	0.0586	0.052*
H6	−0.2079	0.3471	0.0984	0.050*
H8	−0.0532	0.1538	0.1538	0.048*
H9	0.1517	0.0904	0.2026	0.047*
H10	0.3120	0.2553	0.2138	0.041*
H13	0.5731	0.3526	0.1700	0.034*
H18	0.395 (5)	0.330 (4)	0.519 (4)	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0230 (3)	0.0231 (3)	0.0346 (3)	−0.0019 (2)	−0.00360 (19)	0.0024 (3)
N1	0.0251 (19)	0.028 (2)	0.037 (2)	−0.0030 (16)	−0.0018 (15)	−0.0005 (17)
N2	0.0270 (19)	0.030 (2)	0.031 (2)	−0.0005 (17)	−0.0046 (14)	−0.0008 (18)
N3	0.0223 (18)	0.021 (2)	0.026 (2)	0.0014 (14)	−0.0008 (13)	−0.0005 (15)
N4	0.0232 (19)	0.025 (2)	0.033 (2)	0.0029 (15)	−0.0032 (14)	−0.0027 (17)
O1	0.0314 (17)	0.033 (2)	0.049 (2)	0.0107 (15)	−0.0016 (13)	−0.0029 (17)
O2	0.0374 (18)	0.044 (2)	0.032 (2)	0.0038 (15)	0.0071 (13)	−0.0033 (16)
O3	0.044 (2)	0.056 (3)	0.034 (2)	0.0081 (17)	0.0035 (15)	0.0122 (18)
O4	0.041 (2)	0.041 (2)	0.054 (2)	0.0112 (16)	0.0005 (15)	0.0189 (17)
C1	0.047 (3)	0.026 (3)	0.043 (3)	0.001 (2)	−0.006 (2)	0.004 (2)
C2	0.056 (3)	0.035 (3)	0.049 (3)	0.013 (3)	−0.017 (2)	0.006 (3)
C3	0.045 (3)	0.054 (4)	0.036 (3)	0.016 (3)	−0.009 (2)	−0.005 (3)
C4	0.030 (2)	0.048 (3)	0.027 (3)	0.007 (2)	−0.0038 (18)	−0.003 (2)
C5	0.024 (2)	0.071 (4)	0.036 (3)	0.003 (2)	−0.0055 (19)	−0.009 (3)
C6	0.021 (2)	0.060 (4)	0.043 (3)	−0.004 (2)	−0.0029 (18)	−0.005 (3)
C7	0.032 (3)	0.041 (3)	0.029 (3)	−0.010 (2)	0.0021 (18)	−0.005 (2)
C8	0.040 (3)	0.046 (3)	0.035 (3)	−0.016 (2)	0.002 (2)	−0.003 (2)
C9	0.045 (3)	0.027 (3)	0.045 (3)	−0.007 (2)	−0.002 (2)	0.004 (2)
C10	0.033 (2)	0.030 (3)	0.040 (3)	−0.002 (2)	−0.0046 (19)	0.001 (2)
C11	0.022 (2)	0.041 (3)	0.025 (2)	−0.0031 (19)	0.0004 (16)	0.001 (2)
C12	0.023 (2)	0.036 (3)	0.029 (2)	0.0026 (19)	0.0007 (16)	−0.004 (2)
C13	0.023 (2)	0.034 (3)	0.029 (2)	0.0011 (19)	0.0030 (16)	−0.003 (2)
C14	0.024 (2)	0.025 (3)	0.032 (3)	−0.0028 (18)	−0.0013 (17)	−0.008 (2)
C15	0.022 (2)	0.023 (2)	0.028 (2)	−0.0003 (17)	−0.0035 (15)	−0.0006 (19)
C16	0.022 (2)	0.023 (2)	0.026 (2)	−0.0002 (17)	−0.0007 (16)	−0.0014 (18)
C17	0.028 (2)	0.038 (3)	0.038 (3)	−0.003 (2)	−0.003 (2)	0.009 (2)

Geometric parameters (Å, º)

Cu1—N1	2.035 (4)	C2—C3	1.364 (7)
Cu1—N2	2.080 (4)	C2—H2	0.9300
Cu1—N3	2.007 (3)	C3—C4	1.391 (7)
Cu1—N4^i	2.017 (4)	C3—H3	0.9300
Cu1—O1	2.383 (3)	C4—C5	1.451 (7)
Cu1—O4^i	2.509 (4)	C4—C12	1.421 (6)
O1—C14	1.245 (5)	C5—C6	1.338 (8)
O2—C14	1.275 (5)	C5—H5	0.9300
O3—C17	1.300 (6)	C6—C7	1.449 (7)
O4—C17	1.227 (5)	C6—H6	0.9300
N1—C1	1.320 (6)	C7—C8	1.390 (7)
N1—C12	1.363 (5)	C7—C11	1.419 (6)
N2—C10	1.319 (6)	C8—C9	1.366 (7)
N2—C11	1.359 (5)	C8—H8	0.9300
N3—C13	1.347 (5)	C9—C10	1.390 (6)
N3—C15	1.371 (5)	C9—H9	0.9300
N4—Cu1^ii	2.017 (4)	C10—H10	0.9300
N4—C13	1.335 (6)	C11—C12	1.404 (6)
N4—C16	1.372 (5)	C13—H13	0.9300
O3—H18	0.85 (4)	C14—C15	1.484 (6)
C1—C2	1.400 (7)	C15—C16	1.389 (6)
C1—H1	0.9300	C16—C17	1.471 (6)
N1—Cu1—N2	79.88 (15)	C2—C3—C4	119.6 (5)
N1—Cu1—O1	98.11 (13)	C2—C3—H3	120.2
N2—Cu1—O1	90.14 (13)	C3—C2—C1	120.1 (5)
N3—Cu1—N1	167.00 (14)	C3—C2—H2	119.9
N3—Cu1—N2	88.00 (14)	C3—C4—C5	125.0 (5)
N3—Cu1—N4^i	99.24 (13)	C3—C4—C12	117.1 (5)
N3—Cu1—O1	77.07 (12)	C4—C3—H3	120.2
N4^i—Cu1—N1	93.01 (14)	C4—C5—H5	119.2
N4^i—Cu1—N2	172.63 (14)	C5—C6—C7	121.1 (5)
N4^i—Cu1—O1	92.82 (13)	C5—C6—H6	119.4
O4^i—Cu1—N1	83.22 (13)	C6—C5—C4	121.5 (4)
O4^i—Cu1—N2	102.72 (13)	C6—C5—H5	119.2
O4^i—Cu1—N3	104.32 (13)	C7—C6—H6	119.4
O4^i—Cu1—N4^i	74.33 (15)	C8—C7—C6	124.2 (4)
O4^i—Cu1—O1	167.12 (13)	C8—C7—C11	117.3 (4)
N1—C1—C2	122.4 (5)	C7—C8—H8	120.1
N1—C1—H1	118.8	C8—C9—C10	119.4 (5)
N1—C12—C4	122.6 (5)	C8—C9—H9	120.3
N1—C12—C11	116.7 (4)	C9—C8—C7	119.8 (4)
N2—C10—C9	123.1 (4)	C9—C8—H8	120.1
N2—C10—H10	118.4	C9—C10—H10	118.4
N2—C11—C7	122.2 (4)	C10—N2—Cu1	129.8 (3)
N2—C11—C12	117.4 (4)	C10—N2—C11	118.2 (4)
N3—C13—H13	123.7	C10—C9—H9	120.3
N3—C15—C14	120.6 (4)	C11—N2—Cu1	111.9 (3)
N3—C15—C16	108.0 (3)	C11—C7—C6	118.4 (5)
N4—C13—N3	112.7 (4)	C11—C12—C4	120.6 (4)
N4—C13—H13	123.7	C12—N1—Cu1	113.7 (3)
N4—C16—C15	107.9 (4)	C12—C4—C5	117.9 (5)
N4—C16—C17	119.2 (4)	C12—C11—C7	120.4 (4)
O1—C14—O2	125.0 (4)	C13—N3—Cu1	136.0 (3)
O1—C14—C15	117.0 (4)	C13—N3—C15	105.5 (4)
O2—C14—C15	118.0 (4)	C13—N4—Cu1^ii	135.2 (3)
O3—C17—C16	117.4 (4)	C13—N4—C16	105.9 (4)
O4—C17—O3	122.4 (4)	C14—O1—Cu1	109.2 (3)
O4—C17—C16	120.2 (4)	C15—N3—Cu1	114.4 (3)
C1—N1—Cu1	128.2 (3)	C15—C16—C17	132.9 (4)
C1—N1—C12	118.2 (4)	C16—N4—Cu1^ii	118.8 (3)
C1—C2—H2	119.9	C16—C15—C14	131.1 (4)
C2—C1—H1	118.8	C17—O3—H18	115 (4)
Cu1—N1—C1—C2	−179.0 (4)	O1—Cu1—N3—C13	164.5 (4)
Cu1—N1—C12—C4	179.3 (3)	O1—Cu1—N3—C15	11.5 (3)
Cu1—N1—C12—C11	−2.7 (5)	O1—C14—C15—N3	5.1 (6)
Cu1—N2—C10—C9	173.7 (3)	O1—C14—C15—C16	−168.0 (4)
Cu1—N2—C11—C7	−175.8 (3)	O2—C14—C15—C16	9.1 (7)
Cu1—N2—C11—C12	6.9 (5)	O2—C14—C15—N3	−177.8 (4)
Cu1—N3—C13—N4	−154.2 (3)	C1—N1—C12—C4	−1.2 (6)
Cu1—N3—C15—C14	−13.9 (5)	C1—N1—C12—C11	176.8 (4)
Cu1—N3—C15—C16	160.6 (3)	C1—C2—C3—C4	−0.7 (8)
Cu1^ii—N4—C13—N3	176.7 (3)	C2—C3—C4—C5	−178.6 (5)
Cu1^ii—N4—C16—C15	−177.4 (2)	C2—C3—C4—C12	1.1 (7)
Cu1^ii—N4—C16—C17	4.2 (5)	C3—C4—C5—C6	180.0 (5)
Cu1—O1—C14—O2	−172.0 (3)	C3—C4—C12—N1	−0.2 (6)
Cu1—O1—C14—C15	4.8 (4)	C3—C4—C12—C11	−178.1 (4)
N1—Cu1—O1—C14	158.5 (3)	C4—C5—C6—C7	−1.5 (7)
N1—Cu1—N2—C10	178.6 (4)	C5—C6—C7—C8	−175.7 (5)
N1—Cu1—N2—C11	−6.3 (3)	C5—C6—C7—C11	0.8 (7)
N1—Cu1—N3—C13	95.1 (7)	C5—C4—C12—N1	179.6 (4)
N1—Cu1—N3—C15	−57.9 (8)	C5—C4—C12—C11	1.7 (6)
N1—C1—C2—C3	−0.7 (8)	C6—C7—C8—C9	176.5 (4)
N2—Cu1—N1—C1	−174.5 (4)	C6—C7—C11—N2	−176.1 (4)
N2—Cu1—N1—C12	4.8 (3)	C6—C7—C11—C12	1.2 (6)
N2—Cu1—N3—C13	73.9 (4)	C7—C8—C9—C10	−1.0 (7)
N2—Cu1—N3—C15	−79.1 (3)	C7—C11—C12—N1	179.6 (4)
N2—Cu1—O1—C14	78.7 (3)	C7—C11—C12—C4	−2.4 (6)
N2—C11—C12—N1	−3.0 (6)	C8—C7—C11—N2	0.6 (6)
N2—C11—C12—C4	175.0 (4)	C8—C7—C11—C12	177.9 (4)
N3—Cu1—N1—C1	164.0 (6)	C8—C9—C10—N2	1.7 (8)
N3—Cu1—N1—C12	−16.7 (8)	C10—N2—C11—C7	0.0 (6)
N3—Cu1—N2—C10	−6.1 (4)	C10—N2—C11—C12	−177.4 (4)
N3—Cu1—N2—C11	169.0 (3)	C11—N2—C10—C9	−1.2 (7)
N3—Cu1—O1—C14	−9.2 (3)	C11—C7—C8—C9	0.0 (7)
N3—C15—C16—N4	0.0 (4)	C12—N1—C1—C2	1.7 (7)
N3—C15—C16—C17	178.0 (4)	C12—C4—C5—C6	0.3 (7)
N4^i—Cu1—N1—C1	3.5 (4)	C15—N3—C13—N4	0.4 (5)
N4^i—Cu1—N1—C12	−177.1 (3)	C13—N3—C15—C16	−0.2 (4)
N4^i—Cu1—N3—C13	−104.7 (4)	C13—N3—C15—C14	−174.8 (4)
N4^i—Cu1—N3—C15	102.3 (3)	C13—N4—C16—C15	0.2 (4)
N4^i—Cu1—O1—C14	−108.1 (3)	C13—N4—C16—C17	−178.1 (4)
N4—C16—C17—O3	−179.0 (4)	C14—C15—C16—N4	173.8 (4)
N4—C16—C17—O4	1.6 (6)	C14—C15—C16—C17	−8.2 (8)
O1—Cu1—N1—C1	96.8 (4)	C16—N4—C13—N3	−0.4 (5)
O1—Cu1—N1—C12	−83.9 (3)	C15—C16—C17—O3	3.2 (7)
O1—Cu1—N2—C10	−83.2 (4)	C15—C16—C17—O4	−176.3 (4)
O1—Cu1—N2—C11	91.9 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (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
O3—H18···O2	0.85 (4)	1.65 (4)	2.485 (5)	167 (6)