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The title compound, (N-2-aminophenyl-5-methylpyrazolyl­acetamide)dimethoxynickel(II) dichloride, [Ni(C12H14N4O)2(CH3O)2]Cl2, crystallizes in the triclinic space group P\overline 1. The metal atom, located on a center of symmetry, is linked to two organic molecules and has an octahedral coordination, with two N-pyrazole and two O-carbonyl groups equatorial and two methoxy O atoms as axial ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027740/dn6108sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027740/dn6108Isup2.hkl
Contains datablock I

CCDC reference: 236014

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.046
  • wR factor = 0.124
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.90
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.70 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2840 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3007 Completeness (_total/calc) 94.45% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.55 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C9 = 6.76 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 = 5.34 su PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O18 = 3.05 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Cl2 .. C9 = 3.16 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1998); cell refinement: Please provide; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
[Ni(C12H14N4O)2(CH3O)2]Cl2Z = 1
Mr = 648.22F(000) = 338
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2631 (7) ÅCell parameters from 5545 reflections
b = 9.710 (1) Åθ = 2–25.7°
c = 10.957 (1) ŵ = 0.82 mm1
α = 75.810 (5)°T = 293 K
β = 69.703 (7)°Box, blue
γ = 77.549 (7)°0.15 × 0.10 × 0.10 mm
V = 791.09 (14) Å3
Data collection top
Nonius KappaCCD
diffractometer
2530 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25.7°, θmin = 4.4°
φ scansh = 09
5545 measured reflectionsk = 1111
2840 independent reflectionsl = 1212
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.7809P]
where P = (Fo2 + 2Fc2)/3
2723 reflections(Δ/σ)max = 0.004
195 parametersΔρmax = 0.51 e Å3
2 restraintsΔρmin = 0.37 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
Ni10.50000.50000.50000.0335 (2)
Cl20.27723 (11)0.94814 (8)0.33388 (9)0.0480 (2)
O180.4518 (3)0.6386 (2)0.3275 (2)0.0487 (6)
N10.7473 (3)0.5397 (3)0.4271 (3)0.0360 (6)
N20.8879 (3)0.4528 (3)0.3632 (3)0.0366 (6)
H20.88460.36820.35380.044*
O80.4394 (3)0.6633 (2)0.5976 (2)0.0413 (5)
C31.0322 (4)0.5159 (3)0.3169 (3)0.0376 (7)
C40.9849 (4)0.6487 (3)0.3523 (3)0.0391 (7)
H41.05700.71710.33550.047*
C50.8068 (4)0.6594 (3)0.4186 (3)0.0332 (6)
C60.6866 (4)0.7889 (3)0.4663 (3)0.0418 (7)
H6A0.65180.84970.39240.050*
H6B0.75220.84270.49170.050*
C70.5239 (4)0.7616 (3)0.5807 (3)0.0359 (7)
C90.4669 (3)0.8544 (3)0.6634 (3)0.0271 (6)
H90.52650.93210.64360.033*
C100.3193 (4)0.8418 (3)0.7812 (3)0.0405 (7)
C110.1522 (4)0.8399 (3)0.7783 (3)0.0411 (7)
C120.0184 (5)0.8276 (4)0.8993 (4)0.0592 (10)
H120.09370.82280.90130.071*
C130.0510 (6)0.8227 (6)1.0155 (4)0.0736 (13)
H130.03990.81481.09480.088*
C140.2130 (6)0.8292 (6)1.0165 (4)0.0744 (13)
H140.23230.82731.09570.089*
C150.3480 (5)0.8384 (4)0.9000 (4)0.0546 (9)
H150.45930.84250.90020.066*
C161.2020 (5)0.4434 (4)0.2387 (4)0.0568 (9)
H16A1.20070.34160.25800.085*
H16B1.29520.46350.26190.085*
H16C1.21910.47850.14590.085*
N170.1134 (4)0.8453 (3)0.6624 (3)0.0435 (6)
H17B0.193 (4)0.877 (4)0.588 (3)0.052*
H17A0.012 (3)0.887 (4)0.660 (4)0.052*
C190.5789 (7)0.6465 (6)0.1974 (5)0.0781 (13)
H19A0.64780.72050.18250.117*
H19B0.52010.66830.13180.117*
H19C0.65330.55610.19130.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0251 (3)0.0257 (3)0.0502 (4)0.00287 (19)0.0087 (2)0.0128 (2)
Cl20.0477 (5)0.0393 (4)0.0619 (5)0.0041 (3)0.0222 (4)0.0126 (4)
O180.0450 (14)0.0439 (13)0.0533 (14)0.0020 (10)0.0141 (11)0.0076 (10)
N10.0250 (13)0.0294 (12)0.0523 (15)0.0001 (9)0.0088 (11)0.0136 (11)
N20.0283 (13)0.0326 (13)0.0489 (15)0.0012 (10)0.0103 (11)0.0152 (11)
O80.0329 (12)0.0320 (11)0.0585 (14)0.0055 (8)0.0067 (10)0.0182 (10)
C30.0257 (16)0.0446 (17)0.0412 (16)0.0042 (12)0.0080 (12)0.0095 (13)
C40.0346 (17)0.0400 (16)0.0441 (17)0.0124 (13)0.0101 (13)0.0072 (13)
C50.0333 (16)0.0303 (14)0.0373 (15)0.0077 (11)0.0100 (12)0.0071 (11)
C60.0399 (18)0.0304 (15)0.0521 (19)0.0075 (12)0.0071 (14)0.0106 (13)
C70.0336 (16)0.0256 (14)0.0492 (18)0.0011 (11)0.0144 (13)0.0085 (12)
C90.0262 (14)0.0183 (12)0.0371 (14)0.0021 (9)0.0071 (11)0.0104 (10)
C100.0411 (19)0.0349 (16)0.0445 (18)0.0020 (13)0.0115 (14)0.0113 (13)
C110.0394 (18)0.0357 (16)0.0464 (18)0.0006 (12)0.0114 (14)0.0123 (13)
C120.046 (2)0.071 (3)0.056 (2)0.0058 (18)0.0090 (17)0.0149 (19)
C130.061 (3)0.103 (4)0.046 (2)0.011 (2)0.0042 (19)0.012 (2)
C140.070 (3)0.106 (4)0.046 (2)0.006 (2)0.019 (2)0.015 (2)
C150.056 (2)0.062 (2)0.049 (2)0.0059 (17)0.0208 (17)0.0129 (17)
C160.0345 (19)0.063 (2)0.067 (2)0.0014 (16)0.0049 (16)0.0226 (19)
N170.0368 (16)0.0408 (15)0.0528 (17)0.0026 (11)0.0154 (13)0.0136 (12)
C190.070 (3)0.092 (3)0.061 (3)0.012 (2)0.015 (2)0.003 (2)
Geometric parameters (Å, º) top
Ni1—N12.004 (2)C9—C101.436 (4)
Ni1—N1i2.004 (2)C9—H90.9300
Ni1—O8i2.007 (2)C10—C151.393 (5)
Ni1—O82.007 (2)C10—C111.396 (5)
Ni1—O182.141 (2)C11—C121.399 (5)
Ni1—O18i2.141 (2)C11—N171.400 (4)
O18—C191.444 (5)C12—C131.378 (6)
N1—C51.329 (4)C12—H120.9300
N1—N21.362 (3)C13—C141.358 (7)
N2—C31.340 (4)C13—H130.9300
N2—H20.8600C14—C151.372 (6)
O8—C71.243 (4)C14—H140.9300
C3—C41.375 (4)C15—H150.9300
C3—C161.495 (4)C16—H16A0.9600
C4—C51.390 (4)C16—H16B0.9600
C4—H40.9300C16—H16C0.9600
C5—C61.505 (4)N17—H17B0.888 (19)
C6—C71.506 (4)N17—H17A0.860 (19)
C6—H6A0.9700C19—H19A0.9600
C6—H6B0.9700C19—H19B0.9600
C7—C91.332 (4)C19—H19C0.9600
N1—Ni1—N1i180.00 (13)O8—C7—C6124.0 (3)
N1—Ni1—O8i91.10 (9)C9—C7—C6116.2 (3)
N1i—Ni1—O8i88.90 (9)C7—C9—C10124.1 (3)
N1—Ni1—O888.90 (9)C7—C9—H9117.9
N1i—Ni1—O891.10 (9)C10—C9—H9117.9
O8i—Ni1—O8180.0C15—C10—C11120.6 (3)
N1—Ni1—O1888.63 (10)C15—C10—C9116.8 (3)
N1i—Ni1—O1891.37 (10)C11—C10—C9122.5 (3)
O8i—Ni1—O1887.73 (9)C10—C11—C12117.4 (3)
O8—Ni1—O1892.27 (9)C10—C11—N17123.7 (3)
N1—Ni1—O18i91.37 (10)C12—C11—N17118.9 (3)
N1i—Ni1—O18i88.63 (10)C13—C12—C11120.7 (4)
O8i—Ni1—O18i92.27 (9)C13—C12—H12119.7
O8—Ni1—O18i87.73 (9)C11—C12—H12119.7
O18—Ni1—O18i180.0C14—C13—C12121.4 (4)
C19—O18—Ni1122.9 (3)C14—C13—H13119.3
C5—N1—N2105.4 (2)C12—C13—H13119.3
C5—N1—Ni1128.1 (2)C13—C14—C15119.5 (4)
N2—N1—Ni1126.27 (19)C13—C14—H14120.2
C3—N2—N1111.4 (2)C15—C14—H14120.2
C3—N2—H2124.3C14—C15—C10120.4 (4)
N1—N2—H2124.3C14—C15—H15119.8
C7—O8—Ni1129.0 (2)C10—C15—H15119.8
N2—C3—C4106.9 (3)C3—C16—H16A109.5
N2—C3—C16121.2 (3)C3—C16—H16B109.5
C4—C3—C16131.9 (3)H16A—C16—H16B109.5
C3—C4—C5105.7 (3)C3—C16—H16C109.5
C3—C4—H4127.2H16A—C16—H16C109.5
C5—C4—H4127.2H16B—C16—H16C109.5
N1—C5—C4110.7 (3)C11—N17—H17B115 (3)
N1—C5—C6121.7 (3)C11—N17—H17A117 (3)
C4—C5—C6127.4 (3)H17B—N17—H17A109 (4)
C5—C6—C7116.9 (2)O18—C19—H19A109.5
C5—C6—H6A108.1O18—C19—H19B109.5
C7—C6—H6A108.1H19A—C19—H19B109.5
C5—C6—H6B108.1O18—C19—H19C109.5
C7—C6—H6B108.1H19A—C19—H19C109.5
H6A—C6—H6B107.3H19B—C19—H19C109.5
O8—C7—C9119.8 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N17i0.862.122.979 (4)177
N17—H17B···Cl20.89 (2)2.57 (3)3.351 (3)147 (3)
N17—H17A···Cl2ii0.86 (2)2.56 (2)3.406 (3)169 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+2, z+1.
 

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