Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040330/wm2133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040330/wm2133Isup2.hkl |
CCDC reference: 1283855
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.027
- wR factor = 0.066
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
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 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 1.69 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni2 (2) 1.72
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
For the isotypic CoII and ZnII structures, see: Hao et al. (2007); Li et al. (2007).
All chemicals were purchased from Acros Co. Ltd. The title compound was obtained from the hydrothermal reaction (30 ml autoclave at 452 K for 3 d) of NiCl2.6H2O (0.5 mmol), imidazole-4,5-dicarboxylic acid (0.5 mmol), 2,2'-bipyridine (0.5 mmol) and KOH (1 mmol) in 20 ml distilled water. Green crystals were obtained in a yield of approximately 22%. Analysis calculated for C15H9N4NiO4: C 48.96, H 2.47, N 15.23%; Found: C 48.88, H 2.47, N 15.16%.
The H atoms were positioned geometrically and refined as riding atoms with C—H= 0.93 Å and Uiso(H)= 1.2Ueq(C).
In connection with our strucure determination of catena-poly[[(2,2'-bipyridine)cobalt(II)]-µ-imidazole-4,5-dicarboxylato] (Hao et al., 2007), we report here the isotypic structure of the NiII compound. The ZnII analogue (Li et al., 2007) crystallizes also isotypically.
In the title compound, (I), two crystallographically independent monomer units are present in the asymmetric unit. The NiII cations have a distorted octahedral coordination sphere formed by two carboxylate O atoms and by four N atoms, two of which belong to the 2,2'-bipyridine ligand and the other two to the imidazole ring (Fig. 1). The Ni—O and Ni—N bond lengths are in the range of 2.1543 (14)–2.2562 (15) and 2.0775 (17)–2.2721 (17) Å, respectively, and are similar to the M—O and M—N bond lengths (M = Co, Zn) observed in the corresponding isotypic structures. The two carboxylate groups of the imidazole-4,5-dicarboxylate ligand coordinate in a monodentate fashion with the NiII cations, whereby the connectivity between the cations and the ligands gives rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2'-bipyridine ligands are situated in the space between the chains.
For the isotypic CoII and ZnII structures, see: Hao et al. (2007); Li et al. (2007).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
[Ni(C5HN2O4)(C10H8N2)] | F(000) = 1496 |
Mr = 367.97 | Dx = 1.714 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5614 reflections |
a = 20.424 (2) Å | θ = 2.3–26.1° |
b = 9.6712 (10) Å | µ = 1.39 mm−1 |
c = 14.751 (1) Å | T = 293 K |
β = 101.798 (1)° | Cube, green |
V = 2852.1 (4) Å3 | 0.15 × 0.15 × 0.15 mm |
Z = 8 |
Bruker APEXII CCD area-detector diffractometer | 5614 independent reflections |
Radiation source: fine-focus sealed tube | 4906 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −25→20 |
Tmin = 0.819, Tmax = 0.819 | k = −11→10 |
15248 measured reflections | l = −17→18 |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.031P)2 + 1.5005P] where P = (Fo2 + 2Fc2)/3 |
5614 reflections | (Δ/σ)max = 0.039 |
433 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Ni(C5HN2O4)(C10H8N2)] | V = 2852.1 (4) Å3 |
Mr = 367.97 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.424 (2) Å | µ = 1.39 mm−1 |
b = 9.6712 (10) Å | T = 293 K |
c = 14.751 (1) Å | 0.15 × 0.15 × 0.15 mm |
β = 101.798 (1)° |
Bruker APEXII CCD area-detector diffractometer | 5614 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4906 reflections with I > 2σ(I) |
Tmin = 0.819, Tmax = 0.819 | Rint = 0.027 |
15248 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.53 e Å−3 |
5614 reflections | Δρmin = −0.31 e Å−3 |
433 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.70626 (11) | 0.3208 (2) | 0.84600 (14) | 0.0280 (5) | |
H1 | 0.6703 | 0.3795 | 0.8250 | 0.034* | |
C2 | 0.76975 (11) | 0.3757 (2) | 0.86436 (14) | 0.0292 (5) | |
H2 | 0.7765 | 0.4696 | 0.8565 | 0.035* | |
C3 | 0.82307 (11) | 0.2885 (2) | 0.89466 (15) | 0.0313 (5) | |
H3 | 0.8665 | 0.3227 | 0.9076 | 0.038* | |
C4 | 0.81098 (10) | 0.1489 (2) | 0.90560 (14) | 0.0295 (5) | |
H4 | 0.8464 | 0.0881 | 0.9250 | 0.035* | |
C5 | 0.74584 (10) | 0.1011 (2) | 0.88736 (13) | 0.0236 (4) | |
C6 | 0.72867 (10) | −0.0457 (2) | 0.90085 (13) | 0.0243 (4) | |
C7 | 0.77634 (11) | −0.1445 (2) | 0.93791 (14) | 0.0290 (5) | |
H7 | 0.8213 | −0.1206 | 0.9544 | 0.035* | |
C8 | 0.75597 (11) | −0.2782 (2) | 0.94981 (15) | 0.0327 (5) | |
H8 | 0.7872 | −0.3458 | 0.9738 | 0.039* | |
C9 | 0.68885 (11) | −0.3107 (2) | 0.92581 (16) | 0.0330 (5) | |
H9 | 0.6739 | −0.4000 | 0.9335 | 0.040* | |
C10 | 0.64444 (11) | −0.2073 (2) | 0.89007 (15) | 0.0311 (5) | |
H10 | 0.5992 | −0.2288 | 0.8743 | 0.037* | |
C11 | 0.52685 (10) | 0.2341 (2) | 0.94608 (14) | 0.0250 (4) | |
C12 | 0.51350 (9) | 0.3154 (2) | 0.85976 (13) | 0.0226 (4) | |
C13 | 0.52113 (10) | 0.3687 (2) | 0.72120 (14) | 0.0240 (4) | |
H13 | 0.5344 | 0.3682 | 0.6645 | 0.029* | |
C14 | 0.47021 (10) | 0.4233 (2) | 0.82990 (13) | 0.0218 (4) | |
C15 | 0.41987 (10) | 0.4930 (2) | 0.87196 (14) | 0.0249 (4) | |
C16 | 0.86416 (12) | 1.3021 (2) | 0.17951 (16) | 0.0336 (5) | |
H16 | 0.9088 | 1.3170 | 0.2069 | 0.040* | |
C17 | 0.82576 (13) | 1.4144 (2) | 0.14208 (18) | 0.0409 (6) | |
H17 | 0.8443 | 1.5024 | 0.1434 | 0.049* | |
C18 | 0.75971 (13) | 1.3921 (3) | 0.10311 (18) | 0.0425 (6) | |
H18 | 0.7325 | 1.4654 | 0.0779 | 0.051* | |
C19 | 0.73392 (12) | 1.2599 (2) | 0.10156 (15) | 0.0349 (5) | |
H19 | 0.6892 | 1.2432 | 0.0754 | 0.042* | |
C20 | 0.77551 (10) | 1.1524 (2) | 0.13943 (13) | 0.0259 (4) | |
C21 | 0.75113 (10) | 1.0085 (2) | 0.14528 (14) | 0.0256 (4) | |
C22 | 0.68389 (11) | 0.9734 (3) | 0.12219 (16) | 0.0369 (5) | |
H22 | 0.6522 | 1.0388 | 0.0959 | 0.044* | |
C23 | 0.66441 (12) | 0.8402 (3) | 0.13871 (18) | 0.0436 (6) | |
H23 | 0.6195 | 0.8156 | 0.1241 | 0.052* | |
C24 | 0.95914 (9) | 0.7532 (2) | 0.33096 (13) | 0.0207 (4) | |
C25 | 0.77823 (11) | 0.7847 (2) | 0.19550 (15) | 0.0298 (5) | |
H25 | 0.8108 | 0.7201 | 0.2199 | 0.036* | |
C26 | 0.93275 (10) | 0.8466 (2) | 0.39410 (13) | 0.0237 (4) | |
C27 | 1.04263 (9) | 0.5862 (2) | 0.43335 (13) | 0.0213 (4) | |
C28 | 1.00285 (9) | 0.6432 (2) | 0.34751 (13) | 0.0212 (4) | |
C29 | 0.97693 (10) | 0.6785 (2) | 0.20109 (13) | 0.0228 (4) | |
H29 | 0.9748 | 0.6693 | 0.1378 | 0.027* | |
C30 | 0.71208 (11) | 0.7442 (3) | 0.17694 (16) | 0.0383 (6) | |
H30 | 0.7000 | 0.6547 | 0.1898 | 0.046* | |
N1 | 0.69405 (8) | 0.18621 (18) | 0.85704 (11) | 0.0246 (4) | |
N2 | 0.66336 (8) | −0.07771 (18) | 0.87706 (12) | 0.0253 (4) | |
N3 | 0.54579 (8) | 0.28113 (17) | 0.79038 (11) | 0.0235 (4) | |
N4 | 0.47564 (8) | 0.45708 (17) | 0.74142 (11) | 0.0231 (4) | |
N5 | 0.79758 (8) | 0.91347 (18) | 0.17983 (11) | 0.0246 (4) | |
N6 | 0.94283 (8) | 0.77605 (17) | 0.23760 (11) | 0.0219 (4) | |
N7 | 1.01414 (8) | 0.59611 (17) | 0.26445 (11) | 0.0220 (4) | |
N8 | 0.84001 (8) | 1.17327 (18) | 0.17805 (12) | 0.0269 (4) | |
Ni1 | 0.899423 (11) | 0.97523 (2) | 0.214416 (15) | 0.01502 (7) | |
Ni2 | 0.597902 (11) | 0.09584 (2) | 0.819724 (16) | 0.01727 (7) | |
O1 | 0.56785 (7) | 0.13633 (15) | 0.95264 (10) | 0.0299 (3) | |
O2 | 0.49461 (7) | 0.26686 (16) | 1.00906 (10) | 0.0322 (3) | |
O3 | 0.41600 (7) | 0.45809 (16) | 0.95508 (10) | 0.0306 (3) | |
O4 | 0.38170 (7) | 0.57763 (15) | 0.82446 (10) | 0.0296 (3) | |
O5 | 1.03289 (7) | 0.63626 (15) | 0.51070 (9) | 0.0262 (3) | |
O6 | 1.08547 (7) | 0.49642 (14) | 0.42874 (9) | 0.0237 (3) | |
O7 | 0.94594 (8) | 0.81809 (16) | 0.47985 (10) | 0.0344 (4) | |
O8 | 0.89858 (7) | 0.94843 (15) | 0.35916 (9) | 0.0270 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0278 (11) | 0.0235 (11) | 0.0318 (11) | 0.0002 (9) | 0.0040 (9) | 0.0035 (9) |
C2 | 0.0332 (12) | 0.0245 (11) | 0.0292 (11) | −0.0064 (9) | 0.0051 (9) | 0.0023 (9) |
C3 | 0.0241 (11) | 0.0357 (13) | 0.0328 (11) | −0.0075 (9) | 0.0028 (9) | 0.0031 (10) |
C4 | 0.0241 (11) | 0.0297 (12) | 0.0328 (11) | 0.0003 (9) | 0.0013 (9) | 0.0048 (9) |
C5 | 0.0223 (10) | 0.0255 (11) | 0.0218 (10) | 0.0007 (8) | 0.0019 (8) | −0.0001 (8) |
C6 | 0.0221 (10) | 0.0263 (11) | 0.0232 (10) | −0.0004 (8) | 0.0020 (8) | −0.0010 (8) |
C7 | 0.0229 (11) | 0.0315 (12) | 0.0303 (11) | 0.0022 (9) | 0.0003 (8) | −0.0005 (9) |
C8 | 0.0333 (12) | 0.0264 (12) | 0.0359 (12) | 0.0079 (10) | 0.0010 (10) | 0.0044 (10) |
C9 | 0.0357 (13) | 0.0224 (11) | 0.0398 (13) | −0.0014 (9) | 0.0054 (10) | 0.0046 (9) |
C10 | 0.0262 (11) | 0.0296 (12) | 0.0368 (12) | −0.0039 (9) | 0.0045 (9) | 0.0025 (10) |
C11 | 0.0220 (10) | 0.0249 (11) | 0.0260 (10) | −0.0036 (9) | −0.0001 (8) | 0.0002 (9) |
C12 | 0.0190 (10) | 0.0241 (11) | 0.0237 (10) | −0.0020 (8) | 0.0019 (8) | −0.0006 (8) |
C13 | 0.0216 (10) | 0.0264 (11) | 0.0237 (10) | 0.0017 (8) | 0.0038 (8) | 0.0000 (8) |
C14 | 0.0187 (10) | 0.0222 (10) | 0.0234 (10) | −0.0032 (8) | 0.0017 (8) | −0.0004 (8) |
C15 | 0.0218 (10) | 0.0242 (11) | 0.0284 (11) | −0.0039 (8) | 0.0044 (8) | −0.0014 (9) |
C16 | 0.0342 (13) | 0.0281 (12) | 0.0414 (13) | 0.0024 (10) | 0.0145 (10) | 0.0002 (10) |
C17 | 0.0481 (16) | 0.0254 (12) | 0.0533 (15) | 0.0066 (11) | 0.0202 (12) | 0.0045 (11) |
C18 | 0.0441 (15) | 0.0357 (14) | 0.0500 (15) | 0.0196 (11) | 0.0154 (12) | 0.0124 (11) |
C19 | 0.0306 (12) | 0.0398 (14) | 0.0345 (12) | 0.0107 (10) | 0.0067 (10) | 0.0073 (10) |
C20 | 0.0244 (11) | 0.0321 (12) | 0.0223 (10) | 0.0060 (9) | 0.0074 (8) | 0.0028 (9) |
C21 | 0.0225 (11) | 0.0325 (12) | 0.0212 (10) | 0.0036 (9) | 0.0028 (8) | −0.0007 (8) |
C22 | 0.0225 (11) | 0.0456 (15) | 0.0402 (13) | 0.0042 (10) | 0.0008 (10) | −0.0012 (11) |
C23 | 0.0224 (12) | 0.0523 (16) | 0.0536 (15) | −0.0079 (11) | 0.0019 (11) | −0.0087 (13) |
C24 | 0.0189 (10) | 0.0216 (10) | 0.0211 (9) | −0.0006 (8) | 0.0028 (8) | 0.0008 (8) |
C25 | 0.0278 (11) | 0.0269 (12) | 0.0335 (12) | −0.0030 (9) | 0.0034 (9) | 0.0001 (9) |
C26 | 0.0228 (10) | 0.0242 (11) | 0.0237 (10) | 0.0014 (8) | 0.0039 (8) | −0.0001 (8) |
C27 | 0.0196 (10) | 0.0213 (10) | 0.0228 (10) | −0.0026 (8) | 0.0039 (8) | 0.0000 (8) |
C28 | 0.0202 (10) | 0.0217 (10) | 0.0211 (9) | −0.0013 (8) | 0.0027 (8) | −0.0008 (8) |
C29 | 0.0247 (10) | 0.0247 (11) | 0.0183 (9) | 0.0004 (8) | 0.0030 (8) | 0.0000 (8) |
C30 | 0.0339 (13) | 0.0375 (14) | 0.0430 (13) | −0.0103 (11) | 0.0064 (10) | −0.0029 (11) |
N1 | 0.0220 (9) | 0.0239 (9) | 0.0263 (9) | −0.0012 (7) | 0.0013 (7) | 0.0002 (7) |
N2 | 0.0215 (9) | 0.0238 (9) | 0.0297 (9) | −0.0012 (7) | 0.0033 (7) | 0.0019 (7) |
N3 | 0.0213 (9) | 0.0253 (9) | 0.0230 (8) | 0.0009 (7) | 0.0027 (7) | −0.0006 (7) |
N4 | 0.0193 (8) | 0.0249 (9) | 0.0241 (8) | −0.0006 (7) | 0.0018 (7) | 0.0010 (7) |
N5 | 0.0213 (9) | 0.0282 (10) | 0.0243 (9) | 0.0004 (7) | 0.0046 (7) | 0.0010 (7) |
N6 | 0.0229 (9) | 0.0225 (9) | 0.0198 (8) | 0.0008 (7) | 0.0029 (7) | 0.0020 (7) |
N7 | 0.0230 (9) | 0.0221 (9) | 0.0201 (8) | 0.0014 (7) | 0.0028 (7) | −0.0004 (7) |
N8 | 0.0253 (9) | 0.0261 (10) | 0.0300 (9) | 0.0032 (7) | 0.0073 (7) | 0.0010 (8) |
Ni1 | 0.01218 (12) | 0.01396 (13) | 0.01827 (12) | 0.00018 (9) | 0.00154 (9) | 0.00298 (9) |
Ni2 | 0.01201 (12) | 0.01406 (13) | 0.02351 (13) | 0.00011 (9) | −0.00159 (9) | −0.00094 (9) |
O1 | 0.0289 (8) | 0.0294 (8) | 0.0297 (8) | 0.0042 (7) | 0.0017 (6) | 0.0053 (6) |
O2 | 0.0350 (9) | 0.0362 (9) | 0.0261 (8) | 0.0005 (7) | 0.0081 (7) | 0.0033 (7) |
O3 | 0.0313 (8) | 0.0339 (9) | 0.0290 (8) | −0.0002 (7) | 0.0117 (6) | 0.0004 (7) |
O4 | 0.0233 (8) | 0.0314 (8) | 0.0345 (8) | 0.0059 (6) | 0.0067 (6) | 0.0015 (7) |
O5 | 0.0282 (8) | 0.0299 (8) | 0.0197 (7) | 0.0023 (6) | 0.0027 (6) | 0.0006 (6) |
O6 | 0.0213 (7) | 0.0253 (8) | 0.0237 (7) | 0.0044 (6) | 0.0026 (6) | 0.0023 (6) |
O7 | 0.0453 (10) | 0.0375 (9) | 0.0213 (7) | 0.0138 (7) | 0.0086 (7) | 0.0016 (6) |
O8 | 0.0298 (8) | 0.0255 (8) | 0.0262 (7) | 0.0078 (6) | 0.0071 (6) | 0.0017 (6) |
C1—N1 | 1.341 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.376 (3) | C19—C20 | 1.386 (3) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.378 (3) | C20—N8 | 1.339 (3) |
C2—H2 | 0.9300 | C20—C21 | 1.487 (3) |
C3—C4 | 1.388 (3) | C21—N5 | 1.344 (3) |
C3—H3 | 0.9300 | C21—C22 | 1.388 (3) |
C4—C5 | 1.382 (3) | C22—C23 | 1.385 (3) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—N1 | 1.343 (3) | C23—C30 | 1.380 (3) |
C5—C6 | 1.486 (3) | C23—H23 | 0.9300 |
C6—N2 | 1.344 (3) | C24—N6 | 1.367 (2) |
C6—C7 | 1.393 (3) | C24—C28 | 1.378 (3) |
C7—C8 | 1.381 (3) | C24—C26 | 1.477 (3) |
C7—H7 | 0.9300 | C25—N5 | 1.341 (3) |
C8—C9 | 1.380 (3) | C25—C30 | 1.379 (3) |
C8—H8 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.380 (3) | C26—O8 | 1.255 (2) |
C9—H9 | 0.9300 | C26—O7 | 1.269 (2) |
C10—N2 | 1.337 (3) | C27—O6 | 1.244 (2) |
C10—H10 | 0.9300 | C27—O5 | 1.292 (2) |
C11—O1 | 1.253 (2) | C27—C28 | 1.465 (3) |
C11—O2 | 1.283 (2) | C28—N7 | 1.370 (2) |
C11—C12 | 1.474 (3) | C29—N7 | 1.340 (2) |
C12—N3 | 1.367 (3) | C29—N6 | 1.348 (3) |
C12—C14 | 1.380 (3) | C29—H29 | 0.9300 |
C13—N4 | 1.340 (3) | C30—H30 | 0.9300 |
C13—N3 | 1.343 (3) | Ni1—N7i | 2.0869 (16) |
C13—H13 | 0.9300 | Ni1—N6 | 2.1188 (17) |
C14—N4 | 1.372 (3) | Ni1—N5 | 2.1235 (17) |
C14—C15 | 1.469 (3) | Ni1—N8 | 2.2721 (17) |
C15—O4 | 1.243 (2) | Ni1—O8 | 2.1543 (14) |
C15—O3 | 1.290 (2) | Ni1—O6i | 2.2052 (14) |
C16—N8 | 1.338 (3) | Ni2—N4ii | 2.0775 (17) |
C16—C17 | 1.387 (3) | Ni2—N3 | 2.0840 (17) |
C16—H16 | 0.9300 | Ni2—N1 | 2.1167 (17) |
C17—C18 | 1.371 (4) | Ni2—N2 | 2.2040 (17) |
C17—H17 | 0.9300 | Ni2—O1 | 2.2060 (15) |
C18—C19 | 1.381 (3) | Ni2—O4ii | 2.2562 (15) |
N1—C1—C2 | 122.8 (2) | C30—C25—H25 | 118.6 |
N1—C1—H1 | 118.6 | O8—C26—O7 | 124.56 (19) |
C2—C1—H1 | 118.6 | O8—C26—C24 | 117.73 (17) |
C1—C2—C3 | 118.6 (2) | O7—C26—C24 | 117.72 (18) |
C1—C2—H2 | 120.7 | O6—C27—O5 | 123.16 (17) |
C3—C2—H2 | 120.7 | O6—C27—C28 | 119.16 (17) |
C2—C3—C4 | 119.1 (2) | O5—C27—C28 | 117.63 (17) |
C2—C3—H3 | 120.5 | N7—C28—C24 | 108.64 (16) |
C4—C3—H3 | 120.5 | N7—C28—C27 | 118.86 (17) |
C5—C4—C3 | 119.3 (2) | C24—C28—C27 | 131.94 (18) |
C5—C4—H4 | 120.3 | N7—C29—N6 | 113.77 (17) |
C3—C4—H4 | 120.3 | N7—C29—H29 | 123.1 |
N1—C5—C4 | 121.45 (19) | N6—C29—H29 | 123.1 |
N1—C5—C6 | 116.03 (17) | C23—C30—C25 | 118.0 (2) |
C4—C5—C6 | 122.51 (19) | C23—C30—H30 | 121.0 |
N2—C6—C7 | 121.41 (19) | C25—C30—H30 | 121.0 |
N2—C6—C5 | 115.71 (18) | C5—N1—C1 | 118.79 (18) |
C7—C6—C5 | 122.86 (19) | C5—N1—Ni2 | 117.35 (14) |
C8—C7—C6 | 119.2 (2) | C1—N1—Ni2 | 123.69 (14) |
C8—C7—H7 | 120.4 | C10—N2—C6 | 118.62 (18) |
C6—C7—H7 | 120.4 | C10—N2—Ni2 | 126.76 (14) |
C7—C8—C9 | 119.3 (2) | C6—N2—Ni2 | 114.62 (13) |
C7—C8—H8 | 120.3 | C13—N3—C12 | 104.63 (16) |
C9—C8—H8 | 120.3 | C13—N3—Ni2 | 142.82 (14) |
C10—C9—C8 | 118.3 (2) | C12—N3—Ni2 | 110.93 (13) |
C10—C9—H9 | 120.9 | C13—N4—C14 | 104.74 (16) |
C8—C9—H9 | 120.9 | C13—N4—Ni2iii | 141.99 (14) |
N2—C10—C9 | 123.2 (2) | C14—N4—Ni2iii | 112.03 (13) |
N2—C10—H10 | 118.4 | C25—N5—C21 | 119.34 (18) |
C9—C10—H10 | 118.4 | C25—N5—Ni1 | 121.91 (14) |
O1—C11—O2 | 124.32 (19) | C21—N5—Ni1 | 118.67 (14) |
O1—C11—C12 | 118.16 (18) | C29—N6—C24 | 104.46 (16) |
O2—C11—C12 | 117.50 (18) | C29—N6—Ni1 | 143.59 (13) |
N3—C12—C14 | 108.67 (17) | C24—N6—Ni1 | 108.51 (13) |
N3—C12—C11 | 119.01 (18) | C29—N7—C28 | 104.53 (16) |
C14—C12—C11 | 132.26 (19) | C29—N7—Ni1iv | 141.18 (14) |
N4—C13—N3 | 113.74 (18) | C28—N7—Ni1iv | 110.15 (12) |
N4—C13—H13 | 123.1 | C16—N8—C20 | 118.33 (18) |
N3—C13—H13 | 123.1 | C16—N8—Ni1 | 127.12 (15) |
N4—C14—C12 | 108.22 (17) | C20—N8—Ni1 | 113.87 (14) |
N4—C14—C15 | 119.50 (17) | N7i—Ni1—N6 | 99.90 (6) |
C12—C14—C15 | 132.07 (19) | N7i—Ni1—N5 | 161.90 (6) |
O4—C15—O3 | 123.69 (19) | N6—Ni1—N5 | 98.05 (6) |
O4—C15—C14 | 118.47 (18) | N7i—Ni1—O8 | 95.58 (6) |
O3—C15—C14 | 117.78 (18) | N6—Ni1—O8 | 79.55 (6) |
N8—C16—C17 | 123.1 (2) | N5—Ni1—O8 | 89.91 (6) |
N8—C16—H16 | 118.4 | N7i—Ni1—O6i | 79.12 (6) |
C17—C16—H16 | 118.4 | N6—Ni1—O6i | 95.92 (6) |
C18—C17—C16 | 118.1 (2) | N5—Ni1—O6i | 96.78 (6) |
C18—C17—H17 | 120.9 | O8—Ni1—O6i | 172.42 (5) |
C16—C17—H17 | 120.9 | N7i—Ni1—N8 | 87.57 (6) |
C17—C18—C19 | 119.5 (2) | N6—Ni1—N8 | 171.93 (6) |
C17—C18—H18 | 120.3 | N5—Ni1—N8 | 74.38 (6) |
C19—C18—H18 | 120.3 | O8—Ni1—N8 | 102.90 (6) |
C18—C19—C20 | 119.2 (2) | O6i—Ni1—N8 | 82.42 (6) |
C18—C19—H19 | 120.4 | N4ii—Ni2—N3 | 99.91 (6) |
C20—C19—H19 | 120.4 | N4ii—Ni2—N1 | 158.35 (7) |
N8—C20—C19 | 121.8 (2) | N3—Ni2—N1 | 96.10 (7) |
N8—C20—C21 | 115.37 (18) | N4ii—Ni2—N2 | 90.15 (6) |
C19—C20—C21 | 122.7 (2) | N3—Ni2—N2 | 168.11 (6) |
N5—C21—C22 | 120.8 (2) | N1—Ni2—N2 | 75.93 (6) |
N5—C21—C20 | 116.31 (18) | N4ii—Ni2—O1 | 101.11 (6) |
C22—C21—C20 | 122.7 (2) | N3—Ni2—O1 | 78.98 (6) |
C23—C22—C21 | 119.3 (2) | N1—Ni2—O1 | 96.17 (6) |
C23—C22—H22 | 120.3 | N2—Ni2—O1 | 92.94 (6) |
C21—C22—H22 | 120.3 | N4ii—Ni2—O4ii | 78.28 (6) |
C30—C23—C22 | 119.6 (2) | N3—Ni2—O4ii | 93.22 (6) |
C30—C23—H23 | 120.2 | N1—Ni2—O4ii | 86.39 (6) |
C22—C23—H23 | 120.2 | N2—Ni2—O4ii | 95.04 (6) |
N6—C24—C28 | 108.60 (17) | O1—Ni2—O4ii | 171.99 (5) |
N6—C24—C26 | 119.41 (17) | C11—O1—Ni2 | 111.60 (12) |
C28—C24—C26 | 131.89 (18) | C15—O4—Ni2iii | 111.54 (13) |
N5—C25—C30 | 122.8 (2) | C27—O6—Ni1iv | 110.79 (12) |
N5—C25—H25 | 118.6 | C26—O8—Ni1 | 112.64 (12) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C5HN2O4)(C10H8N2)] |
Mr | 367.97 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 20.424 (2), 9.6712 (10), 14.751 (1) |
β (°) | 101.798 (1) |
V (Å3) | 2852.1 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.39 |
Crystal size (mm) | 0.15 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.819, 0.819 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15248, 5614, 4906 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.066, 1.00 |
No. of reflections | 5614 |
No. of parameters | 433 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.31 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
Ni1—N7i | 2.0869 (16) | Ni2—N4ii | 2.0775 (17) |
Ni1—N6 | 2.1188 (17) | Ni2—N3 | 2.0840 (17) |
Ni1—N5 | 2.1235 (17) | Ni2—N1 | 2.1167 (17) |
Ni1—N8 | 2.2721 (17) | Ni2—N2 | 2.2040 (17) |
Ni1—O8 | 2.1543 (14) | Ni2—O1 | 2.2060 (15) |
Ni1—O6i | 2.2052 (14) | Ni2—O4ii | 2.2562 (15) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2. |
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In connection with our strucure determination of catena-poly[[(2,2'-bipyridine)cobalt(II)]-µ-imidazole-4,5-dicarboxylato] (Hao et al., 2007), we report here the isotypic structure of the NiII compound. The ZnII analogue (Li et al., 2007) crystallizes also isotypically.
In the title compound, (I), two crystallographically independent monomer units are present in the asymmetric unit. The NiII cations have a distorted octahedral coordination sphere formed by two carboxylate O atoms and by four N atoms, two of which belong to the 2,2'-bipyridine ligand and the other two to the imidazole ring (Fig. 1). The Ni—O and Ni—N bond lengths are in the range of 2.1543 (14)–2.2562 (15) and 2.0775 (17)–2.2721 (17) Å, respectively, and are similar to the M—O and M—N bond lengths (M = Co, Zn) observed in the corresponding isotypic structures. The two carboxylate groups of the imidazole-4,5-dicarboxylate ligand coordinate in a monodentate fashion with the NiII cations, whereby the connectivity between the cations and the ligands gives rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2'-bipyridine ligands are situated in the space between the chains.