metal-organic compounds
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 CuII 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 CuII atoms are bridged by HIDC2− groups, forming a one-dimensional chain structure. The CuCu separation within the polymer is 6.132 (4) Å. The chains are linked into a two-dimensional supramolecular network via π–π stacking interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029149/is6015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029149/is6015Isup2.hkl |
CCDC reference: 258672
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.055
- wR factor = 0.123
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
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
Computing details top
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'] top
Crystal data top
[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) Å3 | 0.24 × 0.18 × 0.10 mm |
Z = 4 |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.8363P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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—N4i | 2.017 (4) | C3—H3 | 0.9300 |
Cu1—O1 | 2.383 (3) | C4—C5 | 1.451 (7) |
Cu1—O4i | 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—Cu1ii | 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—N4i | 99.24 (13) | C3—C4—C12 | 117.1 (5) |
N3—Cu1—O1 | 77.07 (12) | C4—C3—H3 | 120.2 |
N4i—Cu1—N1 | 93.01 (14) | C4—C5—H5 | 119.2 |
N4i—Cu1—N2 | 172.63 (14) | C5—C6—C7 | 121.1 (5) |
N4i—Cu1—O1 | 92.82 (13) | C5—C6—H6 | 119.4 |
O4i—Cu1—N1 | 83.22 (13) | C6—C5—C4 | 121.5 (4) |
O4i—Cu1—N2 | 102.72 (13) | C6—C5—H5 | 119.2 |
O4i—Cu1—N3 | 104.32 (13) | C7—C6—H6 | 119.4 |
O4i—Cu1—N4i | 74.33 (15) | C8—C7—C6 | 124.2 (4) |
O4i—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—Cu1ii | 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—Cu1ii | 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) |
Cu1ii—N4—C13—N3 | 176.7 (3) | C2—C3—C4—C5 | −178.6 (5) |
Cu1ii—N4—C16—C15 | −177.4 (2) | C2—C3—C4—C12 | 1.1 (7) |
Cu1ii—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) |
N4i—Cu1—N1—C1 | 3.5 (4) | C15—N3—C13—N4 | 0.4 (5) |
N4i—Cu1—N1—C12 | −177.1 (3) | C13—N3—C15—C16 | −0.2 (4) |
N4i—Cu1—N3—C13 | −104.7 (4) | C13—N3—C15—C14 | −174.8 (4) |
N4i—Cu1—N3—C15 | 102.3 (3) | C13—N4—C16—C15 | 0.2 (4) |
N4i—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) top
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) |