Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104018165/dn1058sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104018165/dn1058Isup2.hkl |
CCDC reference: 251297
A water/methanol (1:1, v/v) solution (3 ml) of Zn(Ac)2·2H2O (0.0657 g, 0.3 mmol) was added to a water/methanol (1:1, v/v) solution (3 ml) of 2-nitrobenzoic acid (0.1000 g, 0.6 mmol), NaOH (0.0238 g, 0.6 mmol) and 1,10-phenanthroline (0.593 g, 0.3 mmol). White powder was obtained after several days and then recrystallized with a mixed solvent composed of DMF, methanol and water (1:1:1, v/v/v); white block-shaped crystals were obtained after several days. (Yield 48%.) Analysis calculated for C26H18N4O9Zn: C 52.41, H 3.05, N 9.40%; found: C 52.52, H 2.97, N 9.49%.
All H atoms attached to C atoms were positioned geometrically, with C—H distances of 0.93 Å and Uiso(H) values of 1.2Ueq(C). The H atoms of the water molecules were found in a difference Fourier synthesis and their coordinates were refined using restraints [O—H= 0.85 (2) Å and H···H = 1.39 (2) Å], a Uiso(H) value of 1.5Ueq(O9).
Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: XPREP in SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
[Zn(C7H4NO4)2(C12H8N2)(H2O)] | Z = 2 |
Mr = 595.81 | F(000) = 608 |
Triclinic, P1 | Dx = 1.603 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1418 (5) Å | Cell parameters from 4336 reflections |
b = 11.3396 (6) Å | θ = 1.8–25.1° |
c = 11.9874 (6) Å | µ = 1.06 mm−1 |
α = 97.422 (1)° | T = 293 K |
β = 104.139 (1)° | Block, white |
γ = 108.644 (1)° | 0.76 × 0.32 × 0.12 mm |
V = 1234.03 (11) Å3 |
Siemens SMART CCD diffractometer | 4261 independent reflections |
Radiation source: fine-focus sealed tube | 3775 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.669, Tmax = 0.891 | k = −13→11 |
6301 measured reflections | l = −12→14 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0341P)2 + 1.5531P] where P = (Fo2 + 2Fc2)/3 |
4261 reflections | (Δ/σ)max < 0.001 |
367 parameters | Δρmax = 0.31 e Å−3 |
3 restraints | Δρmin = −0.49 e Å−3 |
[Zn(C7H4NO4)2(C12H8N2)(H2O)] | γ = 108.644 (1)° |
Mr = 595.81 | V = 1234.03 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.1418 (5) Å | Mo Kα radiation |
b = 11.3396 (6) Å | µ = 1.06 mm−1 |
c = 11.9874 (6) Å | T = 293 K |
α = 97.422 (1)° | 0.76 × 0.32 × 0.12 mm |
β = 104.139 (1)° |
Siemens SMART CCD diffractometer | 4261 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3775 reflections with I > 2σ(I) |
Tmin = 0.669, Tmax = 0.891 | Rint = 0.022 |
6301 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 3 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.31 e Å−3 |
4261 reflections | Δρmin = −0.49 e Å−3 |
367 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. |
x | y | z | Uiso*/Ueq | ||
Zn | 0.20199 (4) | 0.38251 (3) | 0.55805 (3) | 0.03530 (13) | |
O1 | 0.1362 (2) | 0.5036 (2) | 0.6585 (2) | 0.0437 (6) | |
O2 | 0.3284 (3) | 0.6798 (2) | 0.6788 (2) | 0.0555 (7) | |
O3 | 0.4828 (3) | 0.8104 (3) | 0.9296 (3) | 0.0756 (10) | |
O4 | 0.4558 (3) | 0.9628 (3) | 0.8476 (3) | 0.0723 (9) | |
O5 | 0.3456 (2) | 0.3791 (2) | 0.70372 (19) | 0.0386 (5) | |
O6 | 0.5209 (3) | 0.4613 (3) | 0.6246 (2) | 0.0527 (7) | |
O7 | 0.5773 (4) | 0.2379 (3) | 0.7085 (3) | 0.0806 (10) | |
O8 | 0.8016 (4) | 0.2793 (4) | 0.8046 (4) | 0.1019 (13) | |
O9 | 0.2626 (2) | 0.5230 (2) | 0.4695 (2) | 0.0399 (5) | |
H91 | 0.297 (4) | 0.582 (3) | 0.532 (2) | 0.060* | |
H92 | 0.330 (3) | 0.522 (4) | 0.440 (3) | 0.060* | |
N1 | 0.2213 (3) | 0.2388 (2) | 0.4309 (2) | 0.0379 (6) | |
N2 | −0.0070 (3) | 0.2417 (2) | 0.5053 (2) | 0.0360 (6) | |
N3 | 0.4080 (3) | 0.8640 (3) | 0.8797 (3) | 0.0511 (8) | |
N4 | 0.6889 (4) | 0.3014 (3) | 0.7878 (3) | 0.0579 (9) | |
C1 | 0.3340 (4) | 0.2390 (4) | 0.3936 (3) | 0.0491 (9) | |
H1 | 0.4198 | 0.3106 | 0.4229 | 0.059* | |
C2 | 0.3305 (5) | 0.1368 (4) | 0.3124 (4) | 0.0576 (10) | |
H2 | 0.4117 | 0.1415 | 0.2876 | 0.069* | |
C3 | 0.2068 (5) | 0.0304 (4) | 0.2704 (3) | 0.0554 (10) | |
H3 | 0.2038 | −0.0393 | 0.2181 | 0.067* | |
C4 | 0.0835 (4) | 0.0260 (3) | 0.3060 (3) | 0.0432 (8) | |
C5 | −0.0519 (5) | −0.0802 (3) | 0.2650 (3) | 0.0553 (10) | |
H5 | −0.0607 | −0.1523 | 0.2125 | 0.066* | |
C6 | −0.1679 (5) | −0.0781 (3) | 0.3010 (4) | 0.0567 (10) | |
H6 | −0.2553 | −0.1482 | 0.2718 | 0.068* | |
C7 | −0.1584 (4) | 0.0303 (3) | 0.3834 (3) | 0.0430 (8) | |
C8 | −0.2742 (4) | 0.0392 (4) | 0.4247 (4) | 0.0542 (10) | |
H8 | −0.3644 | −0.0276 | 0.3977 | 0.065* | |
C9 | −0.2543 (4) | 0.1456 (4) | 0.5043 (4) | 0.0546 (10) | |
H9 | −0.3301 | 0.1517 | 0.5326 | 0.066* | |
C10 | −0.1185 (4) | 0.2453 (3) | 0.5425 (3) | 0.0468 (8) | |
H10 | −0.1057 | 0.3177 | 0.5966 | 0.056* | |
C11 | −0.0255 (3) | 0.1363 (3) | 0.4268 (3) | 0.0347 (7) | |
C12 | 0.0963 (4) | 0.1330 (3) | 0.3869 (3) | 0.0372 (7) | |
C13 | 0.1610 (3) | 0.6933 (3) | 0.7830 (3) | 0.0337 (7) | |
C14 | 0.0144 (4) | 0.6491 (3) | 0.7767 (3) | 0.0388 (7) | |
H14 | −0.0483 | 0.5719 | 0.7252 | 0.047* | |
C15 | −0.0411 (4) | 0.7169 (3) | 0.8452 (3) | 0.0452 (8) | |
H15 | −0.1399 | 0.6851 | 0.8390 | 0.054* | |
C16 | 0.0499 (4) | 0.8314 (4) | 0.9225 (3) | 0.0531 (9) | |
H16 | 0.0125 | 0.8763 | 0.9689 | 0.064* | |
C17 | 0.1968 (4) | 0.8795 (3) | 0.9312 (3) | 0.0482 (9) | |
H17 | 0.2588 | 0.9572 | 0.9824 | 0.058* | |
C18 | 0.2492 (4) | 0.8099 (3) | 0.8624 (3) | 0.0389 (7) | |
C19 | 0.2153 (4) | 0.6206 (3) | 0.7009 (3) | 0.0369 (7) | |
C20 | 0.5880 (3) | 0.4677 (3) | 0.8298 (3) | 0.0341 (7) | |
C21 | 0.6899 (4) | 0.4119 (3) | 0.8672 (3) | 0.0414 (8) | |
C22 | 0.7923 (4) | 0.4552 (4) | 0.9782 (3) | 0.0556 (10) | |
H22 | 0.8594 | 0.4161 | 1.0004 | 0.067* | |
C23 | 0.7931 (5) | 0.5568 (4) | 1.0552 (3) | 0.0603 (11) | |
H23 | 0.8599 | 0.5860 | 1.1306 | 0.072* | |
C24 | 0.6951 (4) | 0.6149 (4) | 1.0203 (3) | 0.0566 (10) | |
H24 | 0.6966 | 0.6841 | 1.0721 | 0.068* | |
C25 | 0.5936 (4) | 0.5714 (3) | 0.9083 (3) | 0.0453 (8) | |
H25 | 0.5286 | 0.6125 | 0.8859 | 0.054* | |
C26 | 0.4783 (3) | 0.4303 (3) | 0.7084 (3) | 0.0347 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0316 (2) | 0.0302 (2) | 0.0334 (2) | 0.00560 (15) | 0.00385 (15) | −0.00240 (15) |
O1 | 0.0392 (13) | 0.0314 (12) | 0.0489 (14) | 0.0052 (10) | 0.0121 (11) | −0.0074 (10) |
O2 | 0.0486 (15) | 0.0417 (14) | 0.0601 (16) | −0.0024 (12) | 0.0261 (13) | −0.0122 (12) |
O3 | 0.0498 (17) | 0.0618 (18) | 0.097 (2) | 0.0261 (15) | −0.0040 (16) | −0.0091 (17) |
O4 | 0.0564 (18) | 0.0535 (18) | 0.087 (2) | −0.0029 (14) | 0.0247 (16) | 0.0015 (16) |
O5 | 0.0294 (12) | 0.0403 (12) | 0.0360 (12) | 0.0050 (10) | 0.0052 (9) | 0.0037 (10) |
O6 | 0.0443 (14) | 0.0705 (17) | 0.0359 (13) | 0.0093 (13) | 0.0144 (11) | 0.0125 (12) |
O7 | 0.065 (2) | 0.0515 (17) | 0.097 (2) | 0.0169 (15) | 0.0039 (18) | −0.0252 (17) |
O8 | 0.089 (3) | 0.101 (3) | 0.117 (3) | 0.069 (2) | 0.003 (2) | −0.005 (2) |
O9 | 0.0396 (13) | 0.0382 (13) | 0.0368 (13) | 0.0119 (10) | 0.0083 (10) | 0.0030 (10) |
N1 | 0.0385 (15) | 0.0334 (14) | 0.0334 (14) | 0.0079 (12) | 0.0075 (12) | −0.0008 (11) |
N2 | 0.0306 (14) | 0.0318 (14) | 0.0383 (15) | 0.0078 (11) | 0.0044 (11) | 0.0041 (11) |
N3 | 0.0435 (17) | 0.0423 (18) | 0.0515 (19) | 0.0091 (15) | 0.0090 (15) | −0.0160 (15) |
N4 | 0.061 (2) | 0.0448 (18) | 0.067 (2) | 0.0255 (17) | 0.0109 (18) | 0.0087 (16) |
C1 | 0.042 (2) | 0.046 (2) | 0.050 (2) | 0.0102 (16) | 0.0130 (17) | −0.0024 (17) |
C2 | 0.062 (3) | 0.056 (2) | 0.054 (2) | 0.020 (2) | 0.026 (2) | −0.0015 (19) |
C3 | 0.076 (3) | 0.043 (2) | 0.045 (2) | 0.023 (2) | 0.018 (2) | −0.0018 (17) |
C4 | 0.056 (2) | 0.0310 (17) | 0.0353 (18) | 0.0147 (15) | 0.0046 (16) | 0.0027 (14) |
C5 | 0.071 (3) | 0.0280 (17) | 0.045 (2) | 0.0058 (17) | 0.0022 (19) | −0.0040 (15) |
C6 | 0.058 (2) | 0.0291 (18) | 0.055 (2) | −0.0040 (17) | 0.0010 (19) | −0.0001 (16) |
C7 | 0.0415 (19) | 0.0310 (17) | 0.0404 (18) | 0.0017 (14) | −0.0016 (15) | 0.0105 (14) |
C8 | 0.0356 (19) | 0.047 (2) | 0.062 (2) | −0.0010 (16) | 0.0045 (17) | 0.0128 (19) |
C9 | 0.036 (2) | 0.052 (2) | 0.067 (3) | 0.0079 (17) | 0.0132 (18) | 0.012 (2) |
C10 | 0.0390 (19) | 0.0426 (19) | 0.053 (2) | 0.0133 (16) | 0.0100 (16) | 0.0044 (16) |
C11 | 0.0398 (17) | 0.0252 (15) | 0.0311 (16) | 0.0090 (13) | 0.0009 (13) | 0.0053 (12) |
C12 | 0.0444 (19) | 0.0291 (16) | 0.0285 (16) | 0.0096 (14) | 0.0010 (14) | 0.0036 (13) |
C13 | 0.0380 (17) | 0.0309 (16) | 0.0287 (15) | 0.0122 (13) | 0.0056 (13) | 0.0050 (13) |
C14 | 0.0385 (18) | 0.0350 (17) | 0.0380 (18) | 0.0106 (14) | 0.0068 (14) | 0.0085 (14) |
C15 | 0.0400 (19) | 0.051 (2) | 0.049 (2) | 0.0186 (16) | 0.0152 (16) | 0.0150 (17) |
C16 | 0.055 (2) | 0.058 (2) | 0.054 (2) | 0.0297 (19) | 0.0239 (19) | 0.0044 (19) |
C17 | 0.052 (2) | 0.0404 (19) | 0.045 (2) | 0.0160 (17) | 0.0119 (17) | −0.0067 (16) |
C18 | 0.0380 (18) | 0.0360 (17) | 0.0366 (17) | 0.0119 (14) | 0.0071 (14) | 0.0000 (14) |
C19 | 0.0386 (18) | 0.0354 (17) | 0.0293 (16) | 0.0123 (15) | 0.0035 (13) | −0.0021 (13) |
C20 | 0.0277 (15) | 0.0334 (16) | 0.0339 (16) | 0.0030 (13) | 0.0089 (13) | 0.0043 (13) |
C21 | 0.0399 (18) | 0.0375 (18) | 0.0429 (19) | 0.0089 (15) | 0.0111 (15) | 0.0126 (15) |
C22 | 0.045 (2) | 0.062 (2) | 0.049 (2) | 0.0121 (18) | 0.0021 (17) | 0.022 (2) |
C23 | 0.054 (2) | 0.067 (3) | 0.0324 (19) | −0.002 (2) | −0.0008 (17) | 0.0080 (19) |
C24 | 0.055 (2) | 0.056 (2) | 0.039 (2) | 0.0012 (19) | 0.0147 (18) | −0.0071 (18) |
C25 | 0.0381 (18) | 0.048 (2) | 0.0429 (19) | 0.0132 (16) | 0.0110 (15) | −0.0029 (16) |
C26 | 0.0358 (17) | 0.0296 (16) | 0.0327 (17) | 0.0084 (13) | 0.0076 (14) | 0.0014 (13) |
Zn—O5 | 1.996 (2) | C6—H6 | 0.9300 |
Zn—O9 | 2.043 (2) | C7—C8 | 1.408 (5) |
Zn—O1 | 2.081 (2) | C7—C11 | 1.412 (4) |
Zn—N2 | 2.089 (3) | C8—C9 | 1.363 (6) |
Zn—N1 | 2.174 (3) | C8—H8 | 0.9300 |
O1—C19 | 1.267 (4) | C9—C10 | 1.396 (5) |
O2—C19 | 1.240 (4) | C9—H9 | 0.9300 |
O3—N3 | 1.212 (4) | C10—H10 | 0.9300 |
O4—N3 | 1.222 (4) | C11—C12 | 1.439 (5) |
O5—C26 | 1.268 (4) | C13—C14 | 1.388 (5) |
O6—C26 | 1.234 (4) | C13—C18 | 1.399 (4) |
O7—N4 | 1.217 (4) | C13—C19 | 1.516 (4) |
O8—N4 | 1.222 (4) | C14—C15 | 1.386 (5) |
O9—H91 | 0.850 (18) | C14—H14 | 0.9300 |
O9—H92 | 0.846 (18) | C15—C16 | 1.378 (5) |
N1—C1 | 1.325 (4) | C15—H15 | 0.9300 |
N1—C12 | 1.365 (4) | C16—C17 | 1.385 (5) |
N2—C10 | 1.322 (4) | C16—H16 | 0.9300 |
N2—C11 | 1.352 (4) | C17—C18 | 1.379 (5) |
N3—C18 | 1.479 (4) | C17—H17 | 0.9300 |
N4—C21 | 1.467 (5) | C20—C25 | 1.385 (5) |
C1—C2 | 1.399 (5) | C20—C21 | 1.391 (5) |
C1—H1 | 0.9300 | C20—C26 | 1.512 (4) |
C2—C3 | 1.360 (6) | C21—C22 | 1.386 (5) |
C2—H2 | 0.9300 | C22—C23 | 1.376 (6) |
C3—C4 | 1.405 (6) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.373 (6) |
C4—C12 | 1.402 (5) | C23—H23 | 0.9300 |
C4—C5 | 1.427 (5) | C24—C25 | 1.390 (5) |
C5—C6 | 1.354 (6) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C6—C7 | 1.435 (5) | ||
O5—Zn—O9 | 119.42 (9) | C10—C9—H9 | 120.6 |
O5—Zn—O1 | 90.25 (9) | N2—C10—C9 | 123.1 (3) |
O9—Zn—O1 | 87.88 (10) | N2—C10—H10 | 118.5 |
O5—Zn—N2 | 117.54 (10) | C9—C10—H10 | 118.5 |
O9—Zn—N2 | 123.02 (10) | N2—C11—C7 | 122.7 (3) |
O1—Zn—N2 | 90.91 (10) | N2—C11—C12 | 118.1 (3) |
O5—Zn—N1 | 99.73 (10) | C7—C11—C12 | 119.1 (3) |
O9—Zn—N1 | 93.45 (10) | N1—C12—C4 | 123.0 (3) |
O1—Zn—N1 | 167.66 (9) | N1—C12—C11 | 116.5 (3) |
N2—Zn—N1 | 78.07 (10) | C4—C12—C11 | 120.6 (3) |
C19—O1—Zn | 121.5 (2) | C14—C13—C18 | 116.2 (3) |
C26—O5—Zn | 114.7 (2) | C14—C13—C19 | 120.1 (3) |
Zn—O9—H91 | 94 (3) | C18—C13—C19 | 123.6 (3) |
Zn—O9—H92 | 115 (3) | C15—C14—C13 | 121.8 (3) |
H91—O9—H92 | 110 (3) | C15—C14—H14 | 119.1 |
C1—N1—C12 | 117.6 (3) | C13—C14—H14 | 119.1 |
C1—N1—Zn | 130.0 (2) | C16—C15—C14 | 120.1 (3) |
C12—N1—Zn | 112.4 (2) | C16—C15—H15 | 119.9 |
C10—N2—C11 | 118.4 (3) | C14—C15—H15 | 119.9 |
C10—N2—Zn | 126.7 (2) | C15—C16—C17 | 120.1 (3) |
C11—N2—Zn | 114.8 (2) | C15—C16—H16 | 119.9 |
O3—N3—O4 | 124.4 (4) | C17—C16—H16 | 119.9 |
O3—N3—C18 | 117.6 (3) | C18—C17—C16 | 118.6 (3) |
O4—N3—C18 | 117.8 (3) | C18—C17—H17 | 120.7 |
O7—N4—O8 | 123.6 (4) | C16—C17—H17 | 120.7 |
O7—N4—C21 | 118.6 (3) | C17—C18—C13 | 123.3 (3) |
O8—N4—C21 | 117.8 (3) | C17—C18—N3 | 115.8 (3) |
N1—C1—C2 | 123.3 (3) | C13—C18—N3 | 120.9 (3) |
N1—C1—H1 | 118.4 | O2—C19—O1 | 126.2 (3) |
C2—C1—H1 | 118.4 | O2—C19—C13 | 118.3 (3) |
C3—C2—C1 | 119.1 (4) | O1—C19—C13 | 115.5 (3) |
C3—C2—H2 | 120.5 | C25—C20—C21 | 117.1 (3) |
C1—C2—H2 | 120.5 | C25—C20—C26 | 117.2 (3) |
C2—C3—C4 | 119.9 (3) | C21—C20—C26 | 125.6 (3) |
C2—C3—H3 | 120.1 | C22—C21—C20 | 122.5 (3) |
C4—C3—H3 | 120.1 | C22—C21—N4 | 118.0 (3) |
C12—C4—C3 | 117.2 (3) | C20—C21—N4 | 119.5 (3) |
C12—C4—C5 | 118.8 (4) | C23—C22—C21 | 119.0 (4) |
C3—C4—C5 | 124.0 (3) | C23—C22—H22 | 120.5 |
C6—C5—C4 | 121.4 (3) | C21—C22—H22 | 120.5 |
C6—C5—H5 | 119.3 | C24—C23—C22 | 119.7 (3) |
C4—C5—H5 | 119.3 | C24—C23—H23 | 120.1 |
C5—C6—C7 | 121.1 (3) | C22—C23—H23 | 120.1 |
C5—C6—H6 | 119.4 | C23—C24—C25 | 120.8 (4) |
C7—C6—H6 | 119.4 | C23—C24—H24 | 119.6 |
C8—C7—C11 | 116.7 (3) | C25—C24—H24 | 119.6 |
C8—C7—C6 | 124.3 (3) | C20—C25—C24 | 120.8 (4) |
C11—C7—C6 | 119.0 (3) | C20—C25—H25 | 119.6 |
C9—C8—C7 | 120.2 (3) | C24—C25—H25 | 119.6 |
C9—C8—H8 | 119.9 | O6—C26—O5 | 124.9 (3) |
C7—C8—H8 | 119.9 | O6—C26—C20 | 119.1 (3) |
C8—C9—C10 | 118.9 (4) | O5—C26—C20 | 115.7 (3) |
C8—C9—H9 | 120.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H91···O2 | 0.85 (2) | 1.85 (3) | 2.678 (3) | 163 (4) |
O9—H92···O6i | 0.85 (2) | 1.83 (4) | 2.671 (3) | 174 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C7H4NO4)2(C12H8N2)(H2O)] |
Mr | 595.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.1418 (5), 11.3396 (6), 11.9874 (6) |
α, β, γ (°) | 97.422 (1), 104.139 (1), 108.644 (1) |
V (Å3) | 1234.03 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.06 |
Crystal size (mm) | 0.76 × 0.32 × 0.12 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.669, 0.891 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6301, 4261, 3775 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.105, 1.13 |
No. of reflections | 4261 |
No. of parameters | 367 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.49 |
Computer programs: SMART (Siemens, 1996), SMART and SAINT (Siemens, 1994), XPREP in SHELXTL (Siemens, 1994), SHELXTL, ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).
Zn—O5 | 1.996 (2) | Zn—N2 | 2.089 (3) |
Zn—O9 | 2.043 (2) | Zn—N1 | 2.174 (3) |
Zn—O1 | 2.081 (2) | ||
O5—Zn—O9 | 119.42 (9) | O1—Zn—N2 | 90.91 (10) |
O5—Zn—O1 | 90.25 (9) | O5—Zn—N1 | 99.73 (10) |
O9—Zn—O1 | 87.88 (10) | O9—Zn—N1 | 93.45 (10) |
O5—Zn—N2 | 117.54 (10) | O1—Zn—N1 | 167.66 (9) |
O9—Zn—N2 | 123.02 (10) | N2—Zn—N1 | 78.07 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H91···O2 | 0.85 (2) | 1.85 (3) | 2.678 (3) | 163 (4) |
O9—H92···O6i | 0.85 (2) | 1.83 (4) | 2.671 (3) | 174 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
Aromatic carboxylic acids have been used extensively in medicine as non-steroidal anti-inflammatory drugs (Stuhlmeier et al., 1999; Emery et al., 2002). The carboxylate ligand can coordinate with metal ions that can have synergetic or antagonistic effects on biological activity. Anti-inflammatory and antibacterial activity of some metal complexes has been found to be higher than that in the parent carboxylic acids (Dendrinou-Samara et al., 1998). Furthermore, the antibacterial effect of some drugs is enhanced when they coordinate with metal ions (Chohan & Sherazi, 1997). It is therefore very important to study the structure and bonding relationships of such complexes, in order to synthesize highly effective antimicrobial species. Recently, we have paid special attention to studying the interactions of aromatic carboxylic acids with zinc, which is a very important element to human beings. Zinc has been known to regulate biological activity in more than 300 metalloenzymes,and zinc and its complexes have antibacterial and antiviral activities (Korant et al., 1974; Simo et al., 2000; Clercq, 1997). Zinc may also act as an antisickling agent and play a very important role in the prevention of pain crisis in sickle-cell disease. To date, zinc has successfully been used in the treatment of several diseases (Cunnane, 1998); a complex of zinc(II) acetate with erythromycin has been used successfully in clinical medicine for acne therapy (Hoogdalem, 1998), and some aliphatic carboxylic acid zinc(II) complexes containing additional N-donor ligands have been found to exhibit some biological activity (Zelenak et al., 2002). In the present study, we report the synthesis and crystal structure of the title complex, (I). The biological activity of (I) against common bacterial strains is to be investigated.
To the best of our knowledge, (I) is the only reported zinc complex containing 2-nitrobenzoate as ligand. Selected geometric parameters are listed in Table 1. As shown in Fig. 1, (I) is a mononuclear neutral zinc(II) complex in which the carboxylate group exhibits a monodentate coordination mode. By contrast, in the mononuclear zinc complex of diaquabis(4-nitrobenzoato)zinc(II), each carboxylate ligand forms a primary and a secondary Zn—O bond (Necefoglu et al., 2001). The Zn ion in (I) is coordinated by two O atoms from two monodentate 2-nitrobenzoate ligands (O1 and O5), two N atoms from the 1,10-phenanthroline (phen) ligand (N1 and N2) and one O atom from the water molecule (O9), and exhibits distorted trigonal-bipyramidal coordination. The trigonal base plane is defined by atom N2 from the phen ligand, atom O5 from the 2-nitrobenzoate ligand and atom O9 from the water molecule. Atom O1 from the 2-nitrobenzoate ligand and atom N1 from the phen ligand occupy the axial positions (O1—Zn—N1 = 167.70°). The Zn—O5 distance [1.995 (2) Å] is shorter than the Zn—O1 distance [2.080 (2) Å]. The Zn—O1 and Zn—O5 distances are both shorter than those observed in some benzoic acid zinc complexes containing N-donor ligands (Zelenak et al., 2004). The distance of atoms Zn and O9 from the coordinated water molecule is 2.046 (2) Å, which is in agreement with the distance (2.053 Å) in the related complex catena-[bis[(µ-Terephthalato)-aqua-(1,10-phenanthroline)zinc]] (Sun et al., 2001). It has been found that many hydrolytic enzymes contain a zinc(II) ion in the active site because zinc-bound water or hydroxide is an excellent nucleophilic agent (Jiang & Guo, 2004). The mean Zn—N distance in (I) [2.132 (s.u.?) Å] is simliar to that in the zinc complex [Zn(SO4)(C12H8N2)(H2O)3]·H2O (2.135 Å; Harvey et al., 2000) but shorter than that in [Zn(C12H8N2)2(H2O)2]SO4·6H2O (2.171 Å; Hu & Liu, 1991). The five-membered chelate ring is nearly planar, with, however, a slight bending [2.2 (s.u.?)°] between the phenanthroline and N2/Zn/N1 planes.
A strong intermolecular hydrogen bond exists, involving the uncoordinated atom O6 of the carboxylate group as an acceptor and atom O9 of the coordinated water molecule as a donor (Table 2), resulting in the formation of dimer (Fig. 2). There is also an intramolecular hydrogen bond between the other H atom of the water molecule and the uncoordinated atom O2 of the other carboxylate group (Table 2).