In the title compound, [Zn(C8H3NO6)(C3H4N2)2]n, each ZnII atom is four-coordinated and bridged by a 5-nitrobenzene-1,3-dicarboxylate ligand to form a one-dimensional herring-bone chain. Interchain hydrogen bonds connect the chains to produce a two-dimensional double-sheet layer. In the crystal structure, all double-sheet layers are stabilized via interlayer π–π interactions between adjacent benzene rings.
Supporting information
CCDC reference: 283766
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.005 Å
- R factor = 0.056
- wR factor = 0.095
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
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Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
catena-poly[[bis(1
H-imidazole-
κN3)zinc(II)]-µ-5-nitrobenzene- 1,3-dicarboxylato-
κ2O1:
O3]
top
Crystal data top
[Zn(C8H3NO6)(C3H4N2)2] | F(000) = 832 |
Mr = 410.65 | Dx = 1.743 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1610 reflections |
a = 9.5225 (16) Å | θ = 2.6–24.0° |
b = 8.6825 (15) Å | µ = 1.62 mm−1 |
c = 19.210 (3) Å | T = 298 K |
β = 99.91 (3)° | Block, colourless |
V = 1564.6 (5) Å3 | 0.18 × 0.14 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3659 independent reflections |
Radiation source: fine-focus sealed tube | 2916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 28.0°, θmin = 2.2° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −11→12 |
Tmin = 0.762, Tmax = 0.890 | k = −8→11 |
27420 measured reflections | l = −25→18 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.011P)2 + 4.62P] where P = (Fo2 + 2Fc2)/3 |
3659 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.5780 (4) | 0.7136 (4) | 0.03112 (18) | 0.0284 (8) | |
C2 | 0.4492 (4) | 0.7004 (4) | 0.05483 (19) | 0.0300 (8) | |
H2 | 0.4442 | 0.6398 | 0.0942 | 0.036* | |
C3 | 0.3277 (3) | 0.7750 (4) | 0.02154 (18) | 0.0266 (7) | |
C4 | 0.3334 (4) | 0.8601 (4) | −0.03910 (19) | 0.0296 (8) | |
H4 | 0.2533 | 0.9119 | −0.0623 | 0.036* | |
C5 | 0.4599 (4) | 0.8660 (4) | −0.06401 (18) | 0.0286 (7) | |
C6 | 0.5833 (4) | 0.7973 (4) | −0.02992 (18) | 0.0295 (8) | |
H6 | 0.6681 | 0.8069 | −0.0474 | 0.035* | |
C7 | 0.7117 (4) | 0.6492 (4) | 0.07531 (19) | 0.0299 (8) | |
C8 | 0.1942 (3) | 0.7721 (4) | 0.05344 (18) | 0.0284 (8) | |
C9 | 0.9125 (4) | 0.7946 (4) | 0.2455 (2) | 0.0341 (8) | |
H9 | 0.8167 | 0.7694 | 0.2322 | 0.041* | |
C10 | 1.1072 (4) | 0.8935 (5) | 0.3040 (2) | 0.0429 (10) | |
H10 | 1.1709 | 0.9478 | 0.3372 | 0.051* | |
C11 | 1.1383 (4) | 0.8093 (5) | 0.2502 (2) | 0.0423 (10) | |
H11 | 1.2292 | 0.7952 | 0.2397 | 0.051* | |
C12 | 0.9652 (5) | 0.3062 (5) | 0.1865 (2) | 0.0409 (10) | |
H12 | 0.9281 | 0.3420 | 0.2252 | 0.049* | |
C13 | 0.9842 (5) | 0.1577 (5) | 0.1716 (2) | 0.0480 (11) | |
H13 | 0.9634 | 0.0728 | 0.1975 | 0.058* | |
C14 | 1.0537 (4) | 0.2998 (5) | 0.0919 (2) | 0.0374 (9) | |
H14 | 1.0905 | 0.3293 | 0.0521 | 0.045* | |
N1 | 0.4669 (4) | 0.9578 (4) | −0.12797 (16) | 0.0349 (7) | |
N2 | 1.0143 (3) | 0.7466 (4) | 0.21246 (15) | 0.0307 (7) | |
N3 | 0.9634 (4) | 0.8834 (4) | 0.30020 (17) | 0.0376 (8) | |
H3 | 0.9143 | 0.9269 | 0.3283 | 0.045* | |
N4 | 1.0084 (3) | 0.3965 (3) | 0.13652 (16) | 0.0302 (7) | |
N5 | 1.0395 (4) | 0.1560 (4) | 0.1115 (2) | 0.0452 (9) | |
H5 | 1.0616 | 0.0752 | 0.0898 | 0.054* | |
O1 | 0.8279 (2) | 0.6843 (3) | 0.05587 (13) | 0.0344 (6) | |
O2 | 0.7024 (3) | 0.5732 (4) | 0.12848 (15) | 0.0456 (7) | |
O3 | 0.1739 (3) | 0.6484 (3) | 0.08612 (15) | 0.0378 (6) | |
O4 | 0.1135 (3) | 0.8837 (3) | 0.04643 (15) | 0.0399 (7) | |
O5 | 0.3562 (3) | 1.0152 (4) | −0.15859 (16) | 0.0532 (8) | |
O6 | 0.5819 (3) | 0.9745 (4) | −0.14659 (15) | 0.0461 (7) | |
Zn | 0.99693 (4) | 0.62360 (5) | 0.12402 (2) | 0.02700 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0267 (17) | 0.031 (2) | 0.0277 (18) | 0.0007 (14) | 0.0042 (14) | 0.0030 (15) |
C2 | 0.0254 (17) | 0.033 (2) | 0.0328 (19) | −0.0003 (15) | 0.0097 (15) | 0.0047 (16) |
C3 | 0.0214 (16) | 0.0283 (19) | 0.0302 (18) | −0.0024 (14) | 0.0052 (14) | −0.0036 (15) |
C4 | 0.0237 (16) | 0.030 (2) | 0.0331 (19) | 0.0025 (14) | −0.0016 (14) | 0.0002 (15) |
C5 | 0.0349 (19) | 0.0277 (19) | 0.0227 (17) | −0.0018 (15) | 0.0034 (14) | −0.0013 (14) |
C6 | 0.0258 (17) | 0.035 (2) | 0.0295 (19) | −0.0020 (15) | 0.0094 (14) | −0.0005 (15) |
C7 | 0.0252 (17) | 0.035 (2) | 0.0296 (19) | 0.0047 (15) | 0.0044 (14) | 0.0006 (15) |
C8 | 0.0210 (16) | 0.034 (2) | 0.0297 (18) | −0.0001 (14) | 0.0036 (14) | −0.0020 (15) |
C9 | 0.033 (2) | 0.033 (2) | 0.036 (2) | 0.0009 (16) | 0.0067 (16) | 0.0023 (16) |
C10 | 0.038 (2) | 0.045 (3) | 0.041 (2) | 0.0044 (19) | −0.0024 (18) | −0.0086 (19) |
C11 | 0.029 (2) | 0.052 (3) | 0.045 (2) | 0.0032 (18) | 0.0055 (17) | −0.008 (2) |
C12 | 0.051 (2) | 0.040 (2) | 0.034 (2) | −0.0053 (19) | 0.0157 (19) | 0.0003 (18) |
C13 | 0.059 (3) | 0.032 (2) | 0.052 (3) | −0.002 (2) | 0.005 (2) | 0.0115 (19) |
C14 | 0.038 (2) | 0.044 (2) | 0.032 (2) | 0.0032 (18) | 0.0097 (17) | −0.0045 (17) |
N1 | 0.044 (2) | 0.0349 (19) | 0.0260 (16) | −0.0009 (15) | 0.0052 (15) | 0.0008 (14) |
N2 | 0.0261 (15) | 0.0344 (17) | 0.0320 (16) | 0.0021 (13) | 0.0062 (12) | −0.0027 (13) |
N3 | 0.0425 (19) | 0.0398 (19) | 0.0319 (17) | 0.0044 (15) | 0.0105 (14) | −0.0071 (14) |
N4 | 0.0302 (16) | 0.0271 (17) | 0.0348 (17) | 0.0032 (13) | 0.0102 (13) | −0.0001 (13) |
N5 | 0.048 (2) | 0.030 (2) | 0.054 (2) | 0.0066 (15) | 0.0018 (17) | −0.0117 (16) |
O1 | 0.0205 (12) | 0.0492 (17) | 0.0344 (14) | 0.0040 (11) | 0.0071 (10) | 0.0110 (12) |
O2 | 0.0332 (15) | 0.0622 (19) | 0.0430 (16) | 0.0086 (14) | 0.0108 (12) | 0.0256 (15) |
O3 | 0.0262 (13) | 0.0401 (16) | 0.0511 (16) | 0.0038 (11) | 0.0182 (12) | 0.0102 (13) |
O4 | 0.0329 (14) | 0.0385 (16) | 0.0498 (17) | 0.0108 (12) | 0.0107 (12) | −0.0018 (13) |
O5 | 0.0487 (18) | 0.066 (2) | 0.0432 (18) | 0.0131 (16) | 0.0037 (14) | 0.0226 (15) |
O6 | 0.0475 (18) | 0.056 (2) | 0.0387 (16) | −0.0037 (14) | 0.0178 (14) | 0.0102 (14) |
Zn | 0.0227 (2) | 0.0286 (2) | 0.0308 (2) | 0.00324 (17) | 0.00743 (16) | 0.00103 (17) |
Geometric parameters (Å, º) top
C1—C2 | 1.385 (5) | C10—H10 | 0.9300 |
C1—C6 | 1.388 (5) | C11—N2 | 1.386 (5) |
C1—C7 | 1.511 (5) | C11—H11 | 0.9300 |
C2—C3 | 1.382 (5) | C12—C13 | 1.340 (6) |
C2—H2 | 0.9300 | C12—N4 | 1.357 (5) |
C3—C4 | 1.389 (5) | C12—H12 | 0.9300 |
C3—C8 | 1.504 (5) | C13—N5 | 1.348 (6) |
C4—C5 | 1.372 (5) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—N5 | 1.318 (5) |
C5—C6 | 1.379 (5) | C14—N4 | 1.324 (5) |
C5—N1 | 1.476 (4) | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | N1—O6 | 1.218 (4) |
C7—O2 | 1.232 (4) | N1—O5 | 1.221 (4) |
C7—O1 | 1.265 (4) | N2—Zn | 1.989 (3) |
C8—O4 | 1.229 (4) | N3—H3 | 0.8600 |
C8—O3 | 1.276 (4) | N4—Zn | 1.987 (3) |
C9—N2 | 1.314 (5) | N5—H5 | 0.8600 |
C9—N3 | 1.326 (5) | O1—Zn | 1.964 (2) |
C9—H9 | 0.9300 | O3—Zni | 1.959 (2) |
C10—C11 | 1.339 (6) | Zn—O3ii | 1.959 (2) |
C10—N3 | 1.361 (5) | | |
| | | |
C2—C1—C6 | 119.0 (3) | C13—C12—N4 | 109.6 (4) |
C2—C1—C7 | 119.5 (3) | C13—C12—H12 | 125.2 |
C6—C1—C7 | 121.2 (3) | N4—C12—H12 | 125.2 |
C3—C2—C1 | 121.8 (3) | C12—C13—N5 | 106.3 (4) |
C3—C2—H2 | 119.1 | C12—C13—H13 | 126.8 |
C1—C2—H2 | 119.1 | N5—C13—H13 | 126.8 |
C2—C3—C4 | 119.2 (3) | N5—C14—N4 | 110.8 (4) |
C2—C3—C8 | 120.2 (3) | N5—C14—H14 | 124.6 |
C4—C3—C8 | 120.5 (3) | N4—C14—H14 | 124.6 |
C5—C4—C3 | 118.4 (3) | O6—N1—O5 | 123.7 (3) |
C5—C4—H4 | 120.8 | O6—N1—C5 | 118.7 (3) |
C3—C4—H4 | 120.8 | O5—N1—C5 | 117.5 (3) |
C4—C5—C6 | 123.1 (3) | C9—N2—C11 | 104.8 (3) |
C4—C5—N1 | 118.6 (3) | C9—N2—Zn | 128.5 (3) |
C6—C5—N1 | 118.2 (3) | C11—N2—Zn | 126.6 (3) |
C5—C6—C1 | 118.4 (3) | C9—N3—C10 | 107.9 (3) |
C5—C6—H6 | 120.8 | C9—N3—H3 | 126.1 |
C1—C6—H6 | 120.8 | C10—N3—H3 | 126.1 |
O2—C7—O1 | 124.4 (3) | C14—N4—C12 | 105.3 (3) |
O2—C7—C1 | 119.4 (3) | C14—N4—Zn | 124.7 (3) |
O1—C7—C1 | 116.1 (3) | C12—N4—Zn | 129.9 (3) |
O4—C8—O3 | 125.0 (3) | C14—N5—C13 | 107.9 (4) |
O4—C8—C3 | 119.9 (3) | C14—N5—H5 | 126.0 |
O3—C8—C3 | 115.1 (3) | C13—N5—H5 | 126.0 |
N2—C9—N3 | 111.6 (3) | C7—O1—Zn | 113.4 (2) |
N2—C9—H9 | 124.2 | C8—O3—Zni | 119.2 (2) |
N3—C9—H9 | 124.2 | O3ii—Zn—O1 | 112.43 (11) |
C11—C10—N3 | 106.1 (4) | O3ii—Zn—N4 | 96.94 (12) |
C11—C10—H10 | 126.9 | O1—Zn—N4 | 111.63 (12) |
N3—C10—H10 | 126.9 | O3ii—Zn—N2 | 107.94 (12) |
C10—C11—N2 | 109.6 (4) | O1—Zn—N2 | 111.31 (12) |
C10—C11—H11 | 125.2 | N4—Zn—N2 | 115.76 (13) |
N2—C11—H11 | 125.2 | | |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O4iii | 0.86 | 1.96 | 2.820 (4) | 176 |
N3—H3···O2iv | 0.86 | 1.96 | 2.799 (4) | 163 |
C10—H10···O3iv | 0.93 | 2.58 | 3.491 (5) | 168 |
C13—H13···N3v | 0.93 | 2.57 | 3.462 (5) | 161 |
C14—H14···O1vi | 0.93 | 2.34 | 3.233 (5) | 161 |
Symmetry codes: (iii) x+1, y−1, z; (iv) −x+3/2, y+1/2, −z+1/2; (v) x, y−1, z; (vi) −x+2, −y+1, −z. |