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The title complex, [Zn(C3H4N2)4](C7H3N2O7)2, consists of a tetrakis(1H-imidazole-κN3)zinc(II) cation and two 2-hydroxy-3,5-dinitrobenzoate anions. In the cation, the ZnII atom, located on a twofold axis, is tetrahedrally coordinated by four N atoms from four imidazole ligands. Intermolecular hydrogen bonds between cations and anions form a supramolecular network.
Supporting information
CCDC reference: 636244
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.102
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C13 .. 5.30 su
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O2
PLAT432_ALERT_2_C Short Inter X...Y Contact O7 .. C13 .. 3.01 Ang.
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
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1998).
Tetrakis(1
H-imidazole-
κN3)zinc(II)
bis(2-hydroxy-3,5-dinitrobenzoate)
top
Crystal data top
[Zn(C3H4N2)4](C7H3N2O7)2 | F(000) = 1616 |
Mr = 791.93 | Dx = 1.664 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3242 reflections |
a = 25.0809 (15) Å | θ = 2.1–26.9° |
b = 6.7251 (4) Å | µ = 0.87 mm−1 |
c = 18.9145 (10) Å | T = 293 K |
β = 97.658 (6)° | Platelet, yellow |
V = 3161.9 (3) Å3 | 0.20 × 0.18 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker APEX-II area-detector diffractometer | 3635 independent reflections |
Radiation source: fine-focus sealed tube | 2431 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 27.6°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −32→31 |
Tmin = 0.846, Tmax = 0.918 | k = −8→8 |
20634 measured reflections | l = −24→24 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.9736P] where P = (Fo2 + 2Fc2)/3 |
3635 reflections | (Δ/σ)max < 0.001 |
241 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.43 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 | 0.47956 (10) | 0.4201 (4) | 0.62640 (15) | 0.0467 (7) | |
H1 | 0.4440 | 0.3982 | 0.6331 | 0.056* | |
C2 | 0.50393 (11) | 0.3370 (4) | 0.57519 (15) | 0.0489 (7) | |
H2 | 0.4889 | 0.2485 | 0.5403 | 0.059* | |
C3 | 0.56023 (10) | 0.5301 (4) | 0.63981 (14) | 0.0401 (6) | |
H3 | 0.5917 | 0.5978 | 0.6568 | 0.048* | |
C4 | 0.59325 (10) | 0.9062 (4) | 0.83994 (14) | 0.0409 (6) | |
H4 | 0.5918 | 0.8232 | 0.8789 | 0.049* | |
N4 | 0.62877 (8) | 1.0508 (4) | 0.83742 (12) | 0.0480 (6) | |
H4A | 0.6540 | 1.0824 | 0.8710 | 0.058* | |
C6 | 0.57669 (11) | 1.0453 (4) | 0.73733 (15) | 0.0452 (7) | |
H6 | 0.5610 | 1.0752 | 0.6912 | 0.054* | |
C7 | 0.73993 (10) | 0.4556 (4) | 0.34201 (13) | 0.0335 (6) | |
C8 | 0.79267 (9) | 0.5060 (4) | 0.36668 (13) | 0.0348 (6) | |
H8 | 0.8179 | 0.5174 | 0.3351 | 0.042* | |
C9 | 0.80716 (9) | 0.5388 (4) | 0.43792 (13) | 0.0317 (6) | |
C10 | 0.77047 (9) | 0.5211 (3) | 0.48947 (13) | 0.0304 (5) | |
C11 | 0.71697 (9) | 0.4592 (3) | 0.46079 (13) | 0.0292 (5) | |
C12 | 0.70275 (9) | 0.4300 (3) | 0.38888 (13) | 0.0322 (6) | |
H12 | 0.6677 | 0.3925 | 0.3716 | 0.039* | |
C13 | 0.67543 (10) | 0.4251 (4) | 0.50850 (13) | 0.0337 (6) | |
N1 | 0.51486 (8) | 0.5428 (3) | 0.66779 (11) | 0.0380 (5) | |
N2 | 0.55506 (9) | 0.4078 (3) | 0.58418 (11) | 0.0446 (6) | |
H2A | 0.5797 | 0.3786 | 0.5584 | 0.054* | |
N3 | 0.56027 (8) | 0.8960 (3) | 0.77957 (10) | 0.0358 (5) | |
C5 | 0.61863 (11) | 1.1401 (4) | 0.77310 (16) | 0.0485 (7) | |
H5 | 0.6372 | 1.2469 | 0.7569 | 0.058* | |
N5 | 0.72384 (9) | 0.4225 (3) | 0.26646 (12) | 0.0428 (6) | |
N6 | 0.86348 (8) | 0.5898 (3) | 0.46074 (13) | 0.0402 (5) | |
O1 | 0.78277 (6) | 0.5520 (3) | 0.55643 (9) | 0.0389 (4) | |
H1A | 0.7562 | 0.5345 | 0.5766 | 0.058* | |
O2 | 0.68863 (7) | 0.4698 (3) | 0.57643 (9) | 0.0420 (4) | |
O3 | 0.63104 (7) | 0.3578 (3) | 0.48667 (9) | 0.0428 (5) | |
O4 | 0.67631 (7) | 0.3836 (3) | 0.24652 (10) | 0.0576 (6) | |
O5 | 0.75771 (8) | 0.4341 (4) | 0.22571 (10) | 0.0663 (7) | |
O6 | 0.89625 (8) | 0.5474 (4) | 0.42010 (11) | 0.0658 (6) | |
O7 | 0.87612 (7) | 0.6734 (3) | 0.51762 (11) | 0.0567 (6) | |
Zn1 | 0.5000 | 0.70909 (7) | 0.7500 | 0.03854 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0321 (14) | 0.0570 (19) | 0.0521 (19) | −0.0059 (13) | 0.0099 (13) | −0.0071 (15) |
C2 | 0.0473 (17) | 0.054 (2) | 0.0452 (18) | −0.0070 (14) | 0.0034 (13) | −0.0099 (14) |
C3 | 0.0335 (14) | 0.0482 (17) | 0.0394 (16) | −0.0054 (12) | 0.0080 (11) | 0.0029 (13) |
C4 | 0.0367 (14) | 0.0502 (18) | 0.0344 (16) | 0.0058 (13) | −0.0008 (12) | 0.0053 (13) |
N4 | 0.0326 (12) | 0.0615 (17) | 0.0466 (16) | −0.0018 (11) | −0.0074 (10) | −0.0042 (12) |
C6 | 0.0426 (16) | 0.0575 (19) | 0.0343 (16) | −0.0019 (13) | 0.0011 (12) | 0.0078 (14) |
C7 | 0.0348 (13) | 0.0375 (15) | 0.0273 (14) | 0.0024 (11) | 0.0003 (10) | −0.0011 (11) |
C8 | 0.0330 (13) | 0.0369 (15) | 0.0354 (15) | 0.0007 (11) | 0.0077 (11) | 0.0031 (11) |
C9 | 0.0259 (12) | 0.0296 (14) | 0.0384 (15) | −0.0024 (10) | −0.0002 (10) | 0.0006 (11) |
C10 | 0.0334 (13) | 0.0245 (13) | 0.0326 (15) | 0.0030 (10) | 0.0012 (10) | −0.0003 (11) |
C11 | 0.0302 (12) | 0.0242 (13) | 0.0331 (14) | 0.0010 (10) | 0.0037 (10) | −0.0008 (10) |
C12 | 0.0291 (13) | 0.0303 (14) | 0.0359 (15) | 0.0006 (10) | −0.0002 (11) | 0.0004 (11) |
C13 | 0.0322 (14) | 0.0320 (14) | 0.0380 (16) | 0.0033 (11) | 0.0083 (11) | −0.0022 (11) |
N1 | 0.0355 (12) | 0.0437 (14) | 0.0358 (13) | −0.0031 (10) | 0.0089 (10) | 0.0003 (10) |
N2 | 0.0431 (13) | 0.0547 (15) | 0.0385 (14) | 0.0034 (11) | 0.0147 (10) | −0.0026 (11) |
N3 | 0.0327 (11) | 0.0445 (13) | 0.0293 (12) | 0.0016 (9) | 0.0012 (9) | 0.0035 (10) |
C5 | 0.0387 (16) | 0.0551 (19) | 0.0511 (19) | −0.0084 (14) | 0.0043 (13) | 0.0064 (15) |
N5 | 0.0408 (13) | 0.0524 (15) | 0.0338 (13) | 0.0039 (11) | 0.0005 (10) | 0.0002 (11) |
N6 | 0.0321 (12) | 0.0434 (14) | 0.0445 (15) | −0.0042 (10) | 0.0029 (11) | 0.0061 (11) |
O1 | 0.0343 (9) | 0.0470 (12) | 0.0345 (11) | −0.0019 (8) | 0.0010 (7) | −0.0048 (8) |
O2 | 0.0441 (10) | 0.0534 (12) | 0.0289 (10) | −0.0031 (9) | 0.0060 (8) | −0.0062 (8) |
O3 | 0.0328 (10) | 0.0561 (12) | 0.0404 (11) | −0.0090 (9) | 0.0083 (8) | −0.0085 (9) |
O4 | 0.0395 (11) | 0.0900 (16) | 0.0404 (12) | −0.0041 (10) | −0.0058 (9) | −0.0049 (11) |
O5 | 0.0501 (12) | 0.114 (2) | 0.0365 (12) | −0.0048 (12) | 0.0125 (10) | −0.0033 (11) |
O6 | 0.0355 (11) | 0.1006 (19) | 0.0639 (15) | −0.0078 (11) | 0.0156 (10) | −0.0114 (13) |
O7 | 0.0423 (11) | 0.0795 (16) | 0.0463 (13) | −0.0181 (10) | −0.0021 (9) | −0.0110 (11) |
Zn1 | 0.0354 (2) | 0.0453 (3) | 0.0352 (3) | 0.000 | 0.00572 (18) | 0.000 |
Geometric parameters (Å, º) top
C1—C2 | 1.335 (4) | C9—C10 | 1.432 (3) |
C1—N1 | 1.376 (3) | C9—N6 | 1.462 (3) |
C1—H1 | 0.9300 | C10—O1 | 1.280 (3) |
C2—N2 | 1.357 (3) | C10—C11 | 1.440 (3) |
C2—H2 | 0.9300 | C11—C12 | 1.374 (3) |
C3—N1 | 1.320 (3) | C11—C13 | 1.484 (3) |
C3—N2 | 1.328 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—O3 | 1.222 (3) |
C4—N3 | 1.319 (3) | C13—O2 | 1.318 (3) |
C4—N4 | 1.324 (3) | N1—Zn1 | 1.990 (2) |
C4—H4 | 0.9300 | N2—H2A | 0.8600 |
N4—C5 | 1.350 (3) | N3—Zn1 | 1.988 (2) |
N4—H4A | 0.8600 | C5—H5 | 0.9300 |
C6—C5 | 1.335 (4) | N5—O5 | 1.223 (3) |
C6—N3 | 1.380 (3) | N5—O4 | 1.230 (3) |
C6—H6 | 0.9300 | N6—O7 | 1.218 (3) |
C7—C12 | 1.380 (3) | N6—O6 | 1.231 (3) |
C7—C8 | 1.385 (3) | O1—H1A | 0.8200 |
C7—N5 | 1.449 (3) | Zn1—N3i | 1.988 (2) |
C8—C9 | 1.366 (3) | Zn1—N1i | 1.990 (2) |
C8—H8 | 0.9300 | | |
| | | |
C2—C1—N1 | 110.0 (2) | C10—C11—C13 | 120.7 (2) |
C2—C1—H1 | 125.0 | C11—C12—C7 | 120.6 (2) |
N1—C1—H1 | 125.0 | C11—C12—H12 | 119.7 |
C1—C2—N2 | 106.2 (2) | C7—C12—H12 | 119.7 |
C1—C2—H2 | 126.9 | O3—C13—O2 | 120.9 (2) |
N2—C2—H2 | 126.9 | O3—C13—C11 | 122.3 (2) |
N1—C3—N2 | 111.1 (2) | O2—C13—C11 | 116.9 (2) |
N1—C3—H3 | 124.5 | C3—N1—C1 | 104.9 (2) |
N2—C3—H3 | 124.5 | C3—N1—Zn1 | 127.64 (18) |
N3—C4—N4 | 110.8 (2) | C1—N1—Zn1 | 127.46 (17) |
N3—C4—H4 | 124.6 | C3—N2—C2 | 107.9 (2) |
N4—C4—H4 | 124.6 | C3—N2—H2A | 126.1 |
C4—N4—C5 | 108.2 (2) | C2—N2—H2A | 126.1 |
C4—N4—H4A | 125.9 | C4—N3—C6 | 105.2 (2) |
C5—N4—H4A | 125.9 | C4—N3—Zn1 | 129.94 (18) |
C5—C6—N3 | 109.3 (2) | C6—N3—Zn1 | 124.86 (17) |
C5—C6—H6 | 125.4 | C6—C5—N4 | 106.6 (2) |
N3—C6—H6 | 125.4 | C6—C5—H5 | 126.7 |
C12—C7—C8 | 120.7 (2) | N4—C5—H5 | 126.7 |
C12—C7—N5 | 119.4 (2) | O5—N5—O4 | 123.1 (2) |
C8—C7—N5 | 119.9 (2) | O5—N5—C7 | 119.1 (2) |
C9—C8—C7 | 119.2 (2) | O4—N5—C7 | 117.8 (2) |
C9—C8—H8 | 120.4 | O7—N6—O6 | 122.8 (2) |
C7—C8—H8 | 120.4 | O7—N6—C9 | 119.8 (2) |
C8—C9—C10 | 123.2 (2) | O6—N6—C9 | 117.4 (2) |
C8—C9—N6 | 116.7 (2) | C10—O1—H1A | 109.5 |
C10—C9—N6 | 120.1 (2) | N3—Zn1—N3i | 101.58 (12) |
O1—C10—C9 | 124.6 (2) | N3—Zn1—N1 | 111.13 (8) |
O1—C10—C11 | 120.6 (2) | N3i—Zn1—N1 | 110.48 (8) |
C9—C10—C11 | 114.7 (2) | N3—Zn1—N1i | 110.48 (8) |
C12—C11—C10 | 121.3 (2) | N3i—Zn1—N1i | 111.13 (8) |
C12—C11—C13 | 118.0 (2) | N1—Zn1—N1i | 111.63 (12) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O1ii | 0.86 | 1.97 | 2.787 (3) | 159 |
N2—H2A···O3 | 0.86 | 2.00 | 2.843 (3) | 168 |
O1—H1A···O2 | 0.82 | 1.75 | 2.502 (2) | 152 |
Symmetry code: (ii) −x+3/2, y+1/2, −z+3/2. |
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