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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055723/dn2111sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055723/dn2111Isup2.hkl
Contains datablock I

CCDC reference: 636244

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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(1H-imidazole-κN3)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) top
Crystal data top
[Zn(C3H4N2)4](C7H3N2O7)2F(000) = 1616
Mr = 791.93Dx = 1.664 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3242 reflections
a = 25.0809 (15) Åθ = 2.1–26.9°
b = 6.7251 (4) ŵ = 0.87 mm1
c = 18.9145 (10) ÅT = 293 K
β = 97.658 (6)°Platelet, yellow
V = 3161.9 (3) Å30.20 × 0.18 × 0.10 mm
Z = 4
Data collection top
Bruker APEX-II area-detector
diffractometer
3635 independent reflections
Radiation source: fine-focus sealed tube2431 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3231
Tmin = 0.846, Tmax = 0.918k = 88
20634 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-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 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.43 e Å3
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
xyzUiso*/Ueq
C10.47956 (10)0.4201 (4)0.62640 (15)0.0467 (7)
H10.44400.39820.63310.056*
C20.50393 (11)0.3370 (4)0.57519 (15)0.0489 (7)
H20.48890.24850.54030.059*
C30.56023 (10)0.5301 (4)0.63981 (14)0.0401 (6)
H30.59170.59780.65680.048*
C40.59325 (10)0.9062 (4)0.83994 (14)0.0409 (6)
H40.59180.82320.87890.049*
N40.62877 (8)1.0508 (4)0.83742 (12)0.0480 (6)
H4A0.65401.08240.87100.058*
C60.57669 (11)1.0453 (4)0.73733 (15)0.0452 (7)
H60.56101.07520.69120.054*
C70.73993 (10)0.4556 (4)0.34201 (13)0.0335 (6)
C80.79267 (9)0.5060 (4)0.36668 (13)0.0348 (6)
H80.81790.51740.33510.042*
C90.80716 (9)0.5388 (4)0.43792 (13)0.0317 (6)
C100.77047 (9)0.5211 (3)0.48947 (13)0.0304 (5)
C110.71697 (9)0.4592 (3)0.46079 (13)0.0292 (5)
C120.70275 (9)0.4300 (3)0.38888 (13)0.0322 (6)
H120.66770.39250.37160.039*
C130.67543 (10)0.4251 (4)0.50850 (13)0.0337 (6)
N10.51486 (8)0.5428 (3)0.66779 (11)0.0380 (5)
N20.55506 (9)0.4078 (3)0.58418 (11)0.0446 (6)
H2A0.57970.37860.55840.054*
N30.56027 (8)0.8960 (3)0.77957 (10)0.0358 (5)
C50.61863 (11)1.1401 (4)0.77310 (16)0.0485 (7)
H50.63721.24690.75690.058*
N50.72384 (9)0.4225 (3)0.26646 (12)0.0428 (6)
N60.86348 (8)0.5898 (3)0.46074 (13)0.0402 (5)
O10.78277 (6)0.5520 (3)0.55643 (9)0.0389 (4)
H1A0.75620.53450.57660.058*
O20.68863 (7)0.4698 (3)0.57643 (9)0.0420 (4)
O30.63104 (7)0.3578 (3)0.48667 (9)0.0428 (5)
O40.67631 (7)0.3836 (3)0.24652 (10)0.0576 (6)
O50.75771 (8)0.4341 (4)0.22571 (10)0.0663 (7)
O60.89625 (8)0.5474 (4)0.42010 (11)0.0658 (6)
O70.87612 (7)0.6734 (3)0.51762 (11)0.0567 (6)
Zn10.50000.70909 (7)0.75000.03854 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0321 (14)0.0570 (19)0.0521 (19)0.0059 (13)0.0099 (13)0.0071 (15)
C20.0473 (17)0.054 (2)0.0452 (18)0.0070 (14)0.0034 (13)0.0099 (14)
C30.0335 (14)0.0482 (17)0.0394 (16)0.0054 (12)0.0080 (11)0.0029 (13)
C40.0367 (14)0.0502 (18)0.0344 (16)0.0058 (13)0.0008 (12)0.0053 (13)
N40.0326 (12)0.0615 (17)0.0466 (16)0.0018 (11)0.0074 (10)0.0042 (12)
C60.0426 (16)0.0575 (19)0.0343 (16)0.0019 (13)0.0011 (12)0.0078 (14)
C70.0348 (13)0.0375 (15)0.0273 (14)0.0024 (11)0.0003 (10)0.0011 (11)
C80.0330 (13)0.0369 (15)0.0354 (15)0.0007 (11)0.0077 (11)0.0031 (11)
C90.0259 (12)0.0296 (14)0.0384 (15)0.0024 (10)0.0002 (10)0.0006 (11)
C100.0334 (13)0.0245 (13)0.0326 (15)0.0030 (10)0.0012 (10)0.0003 (11)
C110.0302 (12)0.0242 (13)0.0331 (14)0.0010 (10)0.0037 (10)0.0008 (10)
C120.0291 (13)0.0303 (14)0.0359 (15)0.0006 (10)0.0002 (11)0.0004 (11)
C130.0322 (14)0.0320 (14)0.0380 (16)0.0033 (11)0.0083 (11)0.0022 (11)
N10.0355 (12)0.0437 (14)0.0358 (13)0.0031 (10)0.0089 (10)0.0003 (10)
N20.0431 (13)0.0547 (15)0.0385 (14)0.0034 (11)0.0147 (10)0.0026 (11)
N30.0327 (11)0.0445 (13)0.0293 (12)0.0016 (9)0.0012 (9)0.0035 (10)
C50.0387 (16)0.0551 (19)0.0511 (19)0.0084 (14)0.0043 (13)0.0064 (15)
N50.0408 (13)0.0524 (15)0.0338 (13)0.0039 (11)0.0005 (10)0.0002 (11)
N60.0321 (12)0.0434 (14)0.0445 (15)0.0042 (10)0.0029 (11)0.0061 (11)
O10.0343 (9)0.0470 (12)0.0345 (11)0.0019 (8)0.0010 (7)0.0048 (8)
O20.0441 (10)0.0534 (12)0.0289 (10)0.0031 (9)0.0060 (8)0.0062 (8)
O30.0328 (10)0.0561 (12)0.0404 (11)0.0090 (9)0.0083 (8)0.0085 (9)
O40.0395 (11)0.0900 (16)0.0404 (12)0.0041 (10)0.0058 (9)0.0049 (11)
O50.0501 (12)0.114 (2)0.0365 (12)0.0048 (12)0.0125 (10)0.0033 (11)
O60.0355 (11)0.1006 (19)0.0639 (15)0.0078 (11)0.0156 (10)0.0114 (13)
O70.0423 (11)0.0795 (16)0.0463 (13)0.0181 (10)0.0021 (9)0.0110 (11)
Zn10.0354 (2)0.0453 (3)0.0352 (3)0.0000.00572 (18)0.000
Geometric parameters (Å, º) top
C1—C21.335 (4)C9—C101.432 (3)
C1—N11.376 (3)C9—N61.462 (3)
C1—H10.9300C10—O11.280 (3)
C2—N21.357 (3)C10—C111.440 (3)
C2—H20.9300C11—C121.374 (3)
C3—N11.320 (3)C11—C131.484 (3)
C3—N21.328 (3)C12—H120.9300
C3—H30.9300C13—O31.222 (3)
C4—N31.319 (3)C13—O21.318 (3)
C4—N41.324 (3)N1—Zn11.990 (2)
C4—H40.9300N2—H2A0.8600
N4—C51.350 (3)N3—Zn11.988 (2)
N4—H4A0.8600C5—H50.9300
C6—C51.335 (4)N5—O51.223 (3)
C6—N31.380 (3)N5—O41.230 (3)
C6—H60.9300N6—O71.218 (3)
C7—C121.380 (3)N6—O61.231 (3)
C7—C81.385 (3)O1—H1A0.8200
C7—N51.449 (3)Zn1—N3i1.988 (2)
C8—C91.366 (3)Zn1—N1i1.990 (2)
C8—H80.9300
C2—C1—N1110.0 (2)C10—C11—C13120.7 (2)
C2—C1—H1125.0C11—C12—C7120.6 (2)
N1—C1—H1125.0C11—C12—H12119.7
C1—C2—N2106.2 (2)C7—C12—H12119.7
C1—C2—H2126.9O3—C13—O2120.9 (2)
N2—C2—H2126.9O3—C13—C11122.3 (2)
N1—C3—N2111.1 (2)O2—C13—C11116.9 (2)
N1—C3—H3124.5C3—N1—C1104.9 (2)
N2—C3—H3124.5C3—N1—Zn1127.64 (18)
N3—C4—N4110.8 (2)C1—N1—Zn1127.46 (17)
N3—C4—H4124.6C3—N2—C2107.9 (2)
N4—C4—H4124.6C3—N2—H2A126.1
C4—N4—C5108.2 (2)C2—N2—H2A126.1
C4—N4—H4A125.9C4—N3—C6105.2 (2)
C5—N4—H4A125.9C4—N3—Zn1129.94 (18)
C5—C6—N3109.3 (2)C6—N3—Zn1124.86 (17)
C5—C6—H6125.4C6—C5—N4106.6 (2)
N3—C6—H6125.4C6—C5—H5126.7
C12—C7—C8120.7 (2)N4—C5—H5126.7
C12—C7—N5119.4 (2)O5—N5—O4123.1 (2)
C8—C7—N5119.9 (2)O5—N5—C7119.1 (2)
C9—C8—C7119.2 (2)O4—N5—C7117.8 (2)
C9—C8—H8120.4O7—N6—O6122.8 (2)
C7—C8—H8120.4O7—N6—C9119.8 (2)
C8—C9—C10123.2 (2)O6—N6—C9117.4 (2)
C8—C9—N6116.7 (2)C10—O1—H1A109.5
C10—C9—N6120.1 (2)N3—Zn1—N3i101.58 (12)
O1—C10—C9124.6 (2)N3—Zn1—N1111.13 (8)
O1—C10—C11120.6 (2)N3i—Zn1—N1110.48 (8)
C9—C10—C11114.7 (2)N3—Zn1—N1i110.48 (8)
C12—C11—C10121.3 (2)N3i—Zn1—N1i111.13 (8)
C12—C11—C13118.0 (2)N1—Zn1—N1i111.63 (12)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1ii0.861.972.787 (3)159
N2—H2A···O30.862.002.843 (3)168
O1—H1A···O20.821.752.502 (2)152
Symmetry code: (ii) x+3/2, y+1/2, z+3/2.
 

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