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In the title mononuclear nickel(II) complex, [Ni(C3H4N2)4](NO3)2, the NiII atom is four-coordinated in a square-planar geometry by four N atoms from four imidazole ligands. The nitrate anions are linked to the nickel(II) complex cations through inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605361X/ci2252sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605361X/ci2252Isup2.hkl
Contains datablock I

CCDC reference: 633661

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.040
  • wR factor = 0.106
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 93 PerFi PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O6 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N9 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N10
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT113_ALERT_2_C ADDSYM Suggests Possible Pseudo/New Spacegroup . Pnna PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ni1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N9 .. 2.70 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O2 .. 2.62 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 4062 Count of symmetry unique reflns 2343 Completeness (_total/calc) 173.37% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1719 Fraction of Friedel pairs measured 0.734 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Tetrakis(1H-imidazole-κN3)nickel(II) dinitrate top
Crystal data top
[Ni(C3H4N2)4](NO3)2F(000) = 936
Mr = 455.06Dx = 1.665 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1321 reflections
a = 13.861 (2) Åθ = 2.3–24.9°
b = 9.793 (3) ŵ = 1.13 mm1
c = 13.372 (2) ÅT = 298 K
V = 1815.1 (7) Å3Block, red
Z = 40.32 × 0.28 × 0.27 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4062 independent reflections
Radiation source: fine-focus sealed tube2724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1817
Tmin = 0.715, Tmax = 0.751k = 129
12776 measured reflectionsl = 1715
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0425P)2 + 1.0722P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4062 reflectionsΔρmax = 0.51 e Å3
263 parametersΔρmin = 0.28 e Å3
1 restraintAbsolute structure: Flack (1983), 1771 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.27 (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
xyzUiso*/Ueq
Ni10.12430 (3)0.49392 (6)0.34211 (16)0.03029 (13)
N10.0202 (2)0.4818 (3)0.3340 (6)0.0350 (9)
N20.1656 (3)0.4233 (5)0.2915 (4)0.0562 (13)
H20.21220.38250.26130.067*
N30.1238 (2)0.3694 (4)0.4620 (3)0.0351 (10)
N40.1225 (3)0.1860 (6)0.5523 (5)0.0459 (14)
H40.12060.10080.56770.055*
N50.2681 (2)0.5096 (3)0.3518 (6)0.0358 (11)
N60.4112 (3)0.5558 (5)0.4063 (5)0.0573 (14)
H60.45690.58420.44450.069*
N70.1256 (2)0.6184 (4)0.2247 (4)0.0368 (10)
N80.1223 (3)0.8051 (6)0.1361 (5)0.0547 (18)
H80.11980.89060.12160.066*
C10.0857 (4)0.5552 (6)0.3892 (5)0.0494 (14)
H10.07010.61970.43760.059*
C20.1749 (4)0.5199 (6)0.3630 (5)0.056 (2)
H2A0.23220.55490.38870.067*
C30.0723 (4)0.4020 (5)0.2762 (4)0.0502 (13)
H30.04730.33940.23080.060*
C40.1269 (4)0.4060 (6)0.5602 (5)0.0503 (14)
H4A0.12920.49520.58400.060*
C50.1261 (4)0.2922 (6)0.6181 (6)0.0562 (17)
H50.12760.28770.68750.067*
C60.1224 (4)0.2369 (6)0.4603 (6)0.0424 (17)
H6A0.12140.18460.40230.051*
C70.3335 (4)0.4670 (6)0.2828 (5)0.0477 (13)
H70.31910.42460.22240.057*
C80.4229 (4)0.4964 (5)0.3166 (6)0.061 (3)
H8A0.48100.47900.28420.073*
C90.3190 (3)0.5635 (5)0.4260 (4)0.0462 (13)
H90.29280.60130.48370.055*
C100.1287 (4)0.5857 (5)0.1238 (5)0.0492 (14)
H100.13140.49770.09780.059*
C110.1271 (4)0.7013 (6)0.0699 (5)0.0491 (15)
H110.12890.70840.00060.059*
C120.1221 (4)0.7525 (6)0.2275 (6)0.0443 (18)
H120.11990.80380.28590.053*
O10.1493 (3)0.2851 (5)0.2357 (4)0.0643 (13)
O20.0693 (4)0.2330 (5)0.1053 (4)0.0804 (15)
O30.1478 (3)0.0794 (3)0.1851 (4)0.0729 (13)
N90.1211 (3)0.1992 (6)0.1765 (5)0.0354 (11)
O50.1053 (3)0.9126 (4)0.4917 (5)0.0865 (18)
O60.1024 (3)0.7047 (6)0.4553 (5)0.0717 (15)
O40.1827 (4)0.7674 (5)0.5811 (4)0.0880 (17)
N100.1306 (3)0.7948 (6)0.5117 (5)0.0409 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03034 (19)0.0326 (2)0.0279 (2)0.0012 (2)0.0031 (3)0.0023 (3)
N10.0378 (16)0.0358 (17)0.031 (3)0.0003 (13)0.001 (3)0.001 (2)
N20.037 (2)0.077 (3)0.054 (3)0.005 (2)0.010 (2)0.004 (3)
N30.041 (2)0.034 (2)0.031 (3)0.0007 (16)0.0038 (16)0.0018 (19)
N40.052 (3)0.042 (3)0.044 (3)0.001 (2)0.003 (2)0.011 (3)
N50.0342 (15)0.0398 (17)0.033 (3)0.0003 (15)0.002 (2)0.0007 (18)
N60.040 (2)0.052 (3)0.080 (4)0.005 (2)0.012 (3)0.007 (3)
N70.040 (2)0.035 (2)0.035 (3)0.0013 (16)0.0031 (17)0.0006 (19)
N80.064 (4)0.028 (3)0.071 (5)0.005 (2)0.003 (3)0.007 (3)
C10.049 (3)0.054 (3)0.046 (3)0.002 (2)0.007 (3)0.005 (3)
C20.039 (3)0.072 (4)0.057 (6)0.008 (3)0.003 (3)0.009 (3)
C30.046 (3)0.054 (3)0.051 (3)0.001 (2)0.006 (2)0.011 (3)
C40.072 (4)0.042 (3)0.037 (4)0.002 (3)0.000 (3)0.008 (3)
C50.071 (4)0.062 (4)0.036 (4)0.003 (3)0.004 (3)0.008 (3)
C60.058 (4)0.030 (3)0.039 (4)0.000 (2)0.003 (3)0.001 (3)
C70.053 (3)0.044 (3)0.046 (3)0.001 (2)0.004 (3)0.007 (3)
C80.037 (3)0.049 (3)0.096 (8)0.005 (2)0.013 (4)0.004 (3)
C90.045 (3)0.050 (3)0.043 (3)0.002 (2)0.010 (2)0.005 (2)
C100.074 (4)0.037 (3)0.036 (4)0.002 (2)0.005 (3)0.001 (2)
C110.064 (4)0.050 (3)0.033 (4)0.003 (3)0.000 (3)0.005 (3)
C120.056 (4)0.044 (4)0.033 (4)0.009 (2)0.004 (3)0.005 (3)
O10.088 (3)0.048 (2)0.057 (3)0.006 (2)0.003 (3)0.026 (2)
O20.080 (3)0.105 (4)0.056 (4)0.023 (3)0.033 (3)0.006 (3)
O30.085 (3)0.030 (2)0.103 (4)0.0053 (17)0.018 (3)0.007 (2)
N90.039 (3)0.034 (2)0.033 (3)0.0003 (18)0.0033 (19)0.005 (2)
O50.064 (2)0.032 (2)0.164 (6)0.0003 (17)0.007 (3)0.018 (3)
O60.081 (3)0.071 (3)0.063 (3)0.007 (3)0.002 (3)0.032 (3)
O40.091 (4)0.108 (4)0.066 (4)0.029 (3)0.031 (4)0.018 (3)
N100.039 (3)0.039 (3)0.044 (4)0.003 (2)0.010 (2)0.001 (3)
Geometric parameters (Å, º) top
Ni1—N71.988 (5)N8—H80.86
Ni1—N52.003 (3)C1—C21.331 (7)
Ni1—N12.009 (3)C1—H10.93
Ni1—N32.014 (5)C2—H2A0.93
N1—C31.316 (7)C3—H30.93
N1—C11.374 (7)C4—C51.357 (8)
N2—C31.326 (6)C4—H4A0.93
N2—C21.351 (8)C5—H50.93
N2—H20.8600C6—H6A0.93
N3—C61.297 (6)C7—C81.350 (8)
N3—C41.363 (7)C7—H70.93
N4—C61.327 (9)C8—H8A0.93
N4—C51.363 (10)C9—H90.93
N4—H40.86C10—C111.343 (8)
N5—C91.327 (8)C10—H100.93
N5—C71.359 (8)C11—H110.93
N6—C91.307 (6)C12—H120.93
N6—C81.343 (9)O1—N91.220 (7)
N6—H60.86O2—N91.237 (7)
N7—C121.315 (7)O3—N91.235 (6)
N7—C101.386 (7)O5—N101.235 (7)
N8—C121.326 (10)O6—N101.225 (8)
N8—C111.350 (10)O4—N101.206 (7)
N7—Ni1—N589.7 (2)N1—C3—N2110.6 (5)
N7—Ni1—N190.2 (2)N1—C3—H3124.7
N5—Ni1—N1178.8 (2)N2—C3—H3124.7
N7—Ni1—N3179.4 (2)C5—C4—N3109.5 (5)
N5—Ni1—N389.9 (2)C5—C4—H4A125.3
N1—Ni1—N390.2 (2)N3—C4—H4A125.3
C3—N1—C1105.3 (4)C4—C5—N4105.0 (7)
C3—N1—Ni1127.9 (4)C4—C5—H5127.5
C1—N1—Ni1126.8 (4)N4—C5—H5127.5
C3—N2—C2108.2 (5)N3—C6—N4111.1 (7)
C3—N2—H2125.9N3—C6—H6A124.5
C2—N2—H2125.9N4—C6—H6A124.5
C6—N3—C4106.3 (5)C8—C7—N5108.6 (5)
C6—N3—Ni1126.3 (5)C8—C7—H7125.7
C4—N3—Ni1127.4 (4)N5—C7—H7125.7
C6—N4—C5108.2 (6)N6—C8—C7106.3 (6)
C6—N4—H4125.9N6—C8—H8A126.9
C5—N4—H4125.9C7—C8—H8A126.9
C9—N5—C7106.0 (4)N6—C9—N5110.2 (5)
C9—N5—Ni1127.4 (4)N6—C9—H9124.9
C7—N5—Ni1126.6 (5)N5—C9—H9124.9
C9—N6—C8108.9 (5)C11—C10—N7109.1 (5)
C9—N6—H6125.6C11—C10—H10125.4
C8—N6—H6125.6N7—C10—H10125.4
C12—N7—C10105.0 (5)C10—C11—N8106.5 (7)
C12—N7—Ni1126.1 (5)C10—C11—H11126.8
C10—N7—Ni1128.8 (4)N8—C11—H11126.8
C12—N8—C11108.2 (6)N7—C12—N8111.2 (6)
C12—N8—H8125.9N7—C12—H12124.4
C11—N8—H8125.9N8—C12—H12124.4
C2—C1—N1109.7 (5)O1—N9—O3119.9 (6)
C2—C1—H1125.2O1—N9—O2120.1 (6)
N1—C1—H1125.2O3—N9—O2120.0 (6)
C1—C2—N2106.2 (5)O4—N10—O6120.3 (7)
C1—C2—H2A126.9O4—N10—O5123.0 (6)
N2—C2—H2A126.9O6—N10—O5116.7 (7)
N7—Ni1—N1—C382.9 (6)C2—N2—C3—N10.6 (7)
N3—Ni1—N1—C397.6 (6)C6—N3—C4—C50.8 (6)
N7—Ni1—N1—C197.8 (6)Ni1—N3—C4—C5179.6 (3)
N3—Ni1—N1—C181.7 (6)N3—C4—C5—N40.1 (6)
N5—Ni1—N3—C696.7 (4)C6—N4—C5—C40.7 (6)
N1—Ni1—N3—C684.5 (4)C4—N3—C6—N41.2 (6)
N5—Ni1—N3—C481.8 (4)Ni1—N3—C6—N4180.0 (3)
N1—Ni1—N3—C497.0 (4)C5—N4—C6—N31.2 (6)
N7—Ni1—N5—C9115.8 (5)C9—N5—C7—C80.2 (7)
N3—Ni1—N5—C963.7 (5)Ni1—N5—C7—C8179.7 (4)
N7—Ni1—N5—C764.1 (5)C9—N6—C8—C70.5 (7)
N3—Ni1—N5—C7116.4 (5)N5—C7—C8—N60.4 (7)
N5—Ni1—N7—C1287.2 (5)C8—N6—C9—N50.4 (7)
N1—Ni1—N7—C1291.6 (5)C7—N5—C9—N60.1 (6)
N5—Ni1—N7—C1093.9 (4)Ni1—N5—C9—N6180.0 (4)
N1—Ni1—N7—C1087.2 (4)C12—N7—C10—C110.1 (6)
C3—N1—C1—C20.8 (8)Ni1—N7—C10—C11179.1 (3)
Ni1—N1—C1—C2179.8 (5)N7—C10—C11—N80.5 (6)
N1—C1—C2—N20.5 (8)C12—N8—C11—C100.7 (6)
C3—N2—C2—C10.1 (7)C10—N7—C12—N80.3 (6)
C1—N1—C3—N20.9 (8)Ni1—N7—C12—N8178.7 (3)
Ni1—N1—C3—N2179.7 (5)C11—N8—C12—N70.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.862.222.953 (6)142
N2—H2···O1i0.862.553.361 (7)158
N2—H2···N9i0.862.703.542 (6)168
N4—H4···O5ii0.862.122.808 (8)137
N6—H6···O5iii0.862.152.939 (7)152
N6—H6···O2iv0.862.623.189 (8)124
N8—H8···O3v0.862.072.787 (7)140
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x, y1, z; (iii) x+1/2, y+3/2, z; (iv) x+1/2, y+1/2, z+1/2; (v) x, y+1, z.
 

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