The title compound, (
N-2-aminophenyl-5-methylpyrazolylacetamide)dimethoxynickel(II) dichloride, [Ni(C
12H
14N
4O)
2(CH
3O)
2]Cl
2, crystallizes in the triclinic space group
P. 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
CCDC reference: 236014
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
Crystal data top
[Ni(C12H14N4O)2(CH3O)2]Cl2 | Z = 1 |
Mr = 648.22 | F(000) = 338 |
Triclinic, P1 | Dx = 1.356 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2631 (7) Å | Cell parameters from 5545 reflections |
b = 9.710 (1) Å | θ = 2–25.7° |
c = 10.957 (1) Å | µ = 0.82 mm−1 |
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 tube | Rint = 0.029 |
Graphite monochromator | θmax = 25.7°, θmin = 4.4° |
φ scans | h = 0→9 |
5545 measured reflections | k = −11→11 |
2840 independent reflections | l = −12→12 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H 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 parameters | Δρmax = 0.51 e Å−3 |
2 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 | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.0335 (2) | |
Cl2 | 0.27723 (11) | 0.94814 (8) | 0.33388 (9) | 0.0480 (2) | |
O18 | 0.4518 (3) | 0.6386 (2) | 0.3275 (2) | 0.0487 (6) | |
N1 | 0.7473 (3) | 0.5397 (3) | 0.4271 (3) | 0.0360 (6) | |
N2 | 0.8879 (3) | 0.4528 (3) | 0.3632 (3) | 0.0366 (6) | |
H2 | 0.8846 | 0.3682 | 0.3538 | 0.044* | |
O8 | 0.4394 (3) | 0.6633 (2) | 0.5976 (2) | 0.0413 (5) | |
C3 | 1.0322 (4) | 0.5159 (3) | 0.3169 (3) | 0.0376 (7) | |
C4 | 0.9849 (4) | 0.6487 (3) | 0.3523 (3) | 0.0391 (7) | |
H4 | 1.0570 | 0.7171 | 0.3355 | 0.047* | |
C5 | 0.8068 (4) | 0.6594 (3) | 0.4186 (3) | 0.0332 (6) | |
C6 | 0.6866 (4) | 0.7889 (3) | 0.4663 (3) | 0.0418 (7) | |
H6A | 0.6518 | 0.8497 | 0.3924 | 0.050* | |
H6B | 0.7522 | 0.8427 | 0.4917 | 0.050* | |
C7 | 0.5239 (4) | 0.7616 (3) | 0.5807 (3) | 0.0359 (7) | |
C9 | 0.4669 (3) | 0.8544 (3) | 0.6634 (3) | 0.0271 (6) | |
H9 | 0.5265 | 0.9321 | 0.6436 | 0.033* | |
C10 | 0.3193 (4) | 0.8418 (3) | 0.7812 (3) | 0.0405 (7) | |
C11 | 0.1522 (4) | 0.8399 (3) | 0.7783 (3) | 0.0411 (7) | |
C12 | 0.0184 (5) | 0.8276 (4) | 0.8993 (4) | 0.0592 (10) | |
H12 | −0.0937 | 0.8228 | 0.9013 | 0.071* | |
C13 | 0.0510 (6) | 0.8227 (6) | 1.0155 (4) | 0.0736 (13) | |
H13 | −0.0399 | 0.8148 | 1.0948 | 0.088* | |
C14 | 0.2130 (6) | 0.8292 (6) | 1.0165 (4) | 0.0744 (13) | |
H14 | 0.2323 | 0.8273 | 1.0957 | 0.089* | |
C15 | 0.3480 (5) | 0.8384 (4) | 0.9000 (4) | 0.0546 (9) | |
H15 | 0.4593 | 0.8425 | 0.9002 | 0.066* | |
C16 | 1.2020 (5) | 0.4434 (4) | 0.2387 (4) | 0.0568 (9) | |
H16A | 1.2007 | 0.3416 | 0.2580 | 0.085* | |
H16B | 1.2952 | 0.4635 | 0.2619 | 0.085* | |
H16C | 1.2191 | 0.4785 | 0.1459 | 0.085* | |
N17 | 0.1134 (4) | 0.8453 (3) | 0.6624 (3) | 0.0435 (6) | |
H17B | 0.193 (4) | 0.877 (4) | 0.588 (3) | 0.052* | |
H17A | 0.012 (3) | 0.887 (4) | 0.660 (4) | 0.052* | |
C19 | 0.5789 (7) | 0.6465 (6) | 0.1974 (5) | 0.0781 (13) | |
H19A | 0.6478 | 0.7205 | 0.1825 | 0.117* | |
H19B | 0.5201 | 0.6683 | 0.1318 | 0.117* | |
H19C | 0.6533 | 0.5561 | 0.1913 | 0.117* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0251 (3) | 0.0257 (3) | 0.0502 (4) | −0.00287 (19) | −0.0087 (2) | −0.0128 (2) |
Cl2 | 0.0477 (5) | 0.0393 (4) | 0.0619 (5) | −0.0041 (3) | −0.0222 (4) | −0.0126 (4) |
O18 | 0.0450 (14) | 0.0439 (13) | 0.0533 (14) | −0.0020 (10) | −0.0141 (11) | −0.0076 (10) |
N1 | 0.0250 (13) | 0.0294 (12) | 0.0523 (15) | 0.0001 (9) | −0.0088 (11) | −0.0136 (11) |
N2 | 0.0283 (13) | 0.0326 (13) | 0.0489 (15) | 0.0012 (10) | −0.0103 (11) | −0.0152 (11) |
O8 | 0.0329 (12) | 0.0320 (11) | 0.0585 (14) | −0.0055 (8) | −0.0067 (10) | −0.0182 (10) |
C3 | 0.0257 (16) | 0.0446 (17) | 0.0412 (16) | −0.0042 (12) | −0.0080 (12) | −0.0095 (13) |
C4 | 0.0346 (17) | 0.0400 (16) | 0.0441 (17) | −0.0124 (13) | −0.0101 (13) | −0.0072 (13) |
C5 | 0.0333 (16) | 0.0303 (14) | 0.0373 (15) | −0.0077 (11) | −0.0100 (12) | −0.0071 (11) |
C6 | 0.0399 (18) | 0.0304 (15) | 0.0521 (19) | −0.0075 (12) | −0.0071 (14) | −0.0106 (13) |
C7 | 0.0336 (16) | 0.0256 (14) | 0.0492 (18) | −0.0011 (11) | −0.0144 (13) | −0.0085 (12) |
C9 | 0.0262 (14) | 0.0183 (12) | 0.0371 (14) | −0.0021 (9) | −0.0071 (11) | −0.0104 (10) |
C10 | 0.0411 (19) | 0.0349 (16) | 0.0445 (18) | −0.0020 (13) | −0.0115 (14) | −0.0113 (13) |
C11 | 0.0394 (18) | 0.0357 (16) | 0.0464 (18) | 0.0006 (12) | −0.0114 (14) | −0.0123 (13) |
C12 | 0.046 (2) | 0.071 (3) | 0.056 (2) | −0.0058 (18) | −0.0090 (17) | −0.0149 (19) |
C13 | 0.061 (3) | 0.103 (4) | 0.046 (2) | −0.011 (2) | −0.0042 (19) | −0.012 (2) |
C14 | 0.070 (3) | 0.106 (4) | 0.046 (2) | −0.006 (2) | −0.019 (2) | −0.015 (2) |
C15 | 0.056 (2) | 0.062 (2) | 0.049 (2) | −0.0059 (17) | −0.0208 (17) | −0.0129 (17) |
C16 | 0.0345 (19) | 0.063 (2) | 0.067 (2) | −0.0014 (16) | −0.0049 (16) | −0.0226 (19) |
N17 | 0.0368 (16) | 0.0408 (15) | 0.0528 (17) | 0.0026 (11) | −0.0154 (13) | −0.0136 (12) |
C19 | 0.070 (3) | 0.092 (3) | 0.061 (3) | −0.012 (2) | −0.015 (2) | −0.003 (2) |
Geometric parameters (Å, º) top
Ni1—N1 | 2.004 (2) | C9—C10 | 1.436 (4) |
Ni1—N1i | 2.004 (2) | C9—H9 | 0.9300 |
Ni1—O8i | 2.007 (2) | C10—C15 | 1.393 (5) |
Ni1—O8 | 2.007 (2) | C10—C11 | 1.396 (5) |
Ni1—O18 | 2.141 (2) | C11—C12 | 1.399 (5) |
Ni1—O18i | 2.141 (2) | C11—N17 | 1.400 (4) |
O18—C19 | 1.444 (5) | C12—C13 | 1.378 (6) |
N1—C5 | 1.329 (4) | C12—H12 | 0.9300 |
N1—N2 | 1.362 (3) | C13—C14 | 1.358 (7) |
N2—C3 | 1.340 (4) | C13—H13 | 0.9300 |
N2—H2 | 0.8600 | C14—C15 | 1.372 (6) |
O8—C7 | 1.243 (4) | C14—H14 | 0.9300 |
C3—C4 | 1.375 (4) | C15—H15 | 0.9300 |
C3—C16 | 1.495 (4) | C16—H16A | 0.9600 |
C4—C5 | 1.390 (4) | C16—H16B | 0.9600 |
C4—H4 | 0.9300 | C16—H16C | 0.9600 |
C5—C6 | 1.505 (4) | N17—H17B | 0.888 (19) |
C6—C7 | 1.506 (4) | N17—H17A | 0.860 (19) |
C6—H6A | 0.9700 | C19—H19A | 0.9600 |
C6—H6B | 0.9700 | C19—H19B | 0.9600 |
C7—C9 | 1.332 (4) | C19—H19C | 0.9600 |
| | | |
N1—Ni1—N1i | 180.00 (13) | O8—C7—C6 | 124.0 (3) |
N1—Ni1—O8i | 91.10 (9) | C9—C7—C6 | 116.2 (3) |
N1i—Ni1—O8i | 88.90 (9) | C7—C9—C10 | 124.1 (3) |
N1—Ni1—O8 | 88.90 (9) | C7—C9—H9 | 117.9 |
N1i—Ni1—O8 | 91.10 (9) | C10—C9—H9 | 117.9 |
O8i—Ni1—O8 | 180.0 | C15—C10—C11 | 120.6 (3) |
N1—Ni1—O18 | 88.63 (10) | C15—C10—C9 | 116.8 (3) |
N1i—Ni1—O18 | 91.37 (10) | C11—C10—C9 | 122.5 (3) |
O8i—Ni1—O18 | 87.73 (9) | C10—C11—C12 | 117.4 (3) |
O8—Ni1—O18 | 92.27 (9) | C10—C11—N17 | 123.7 (3) |
N1—Ni1—O18i | 91.37 (10) | C12—C11—N17 | 118.9 (3) |
N1i—Ni1—O18i | 88.63 (10) | C13—C12—C11 | 120.7 (4) |
O8i—Ni1—O18i | 92.27 (9) | C13—C12—H12 | 119.7 |
O8—Ni1—O18i | 87.73 (9) | C11—C12—H12 | 119.7 |
O18—Ni1—O18i | 180.0 | C14—C13—C12 | 121.4 (4) |
C19—O18—Ni1 | 122.9 (3) | C14—C13—H13 | 119.3 |
C5—N1—N2 | 105.4 (2) | C12—C13—H13 | 119.3 |
C5—N1—Ni1 | 128.1 (2) | C13—C14—C15 | 119.5 (4) |
N2—N1—Ni1 | 126.27 (19) | C13—C14—H14 | 120.2 |
C3—N2—N1 | 111.4 (2) | C15—C14—H14 | 120.2 |
C3—N2—H2 | 124.3 | C14—C15—C10 | 120.4 (4) |
N1—N2—H2 | 124.3 | C14—C15—H15 | 119.8 |
C7—O8—Ni1 | 129.0 (2) | C10—C15—H15 | 119.8 |
N2—C3—C4 | 106.9 (3) | C3—C16—H16A | 109.5 |
N2—C3—C16 | 121.2 (3) | C3—C16—H16B | 109.5 |
C4—C3—C16 | 131.9 (3) | H16A—C16—H16B | 109.5 |
C3—C4—C5 | 105.7 (3) | C3—C16—H16C | 109.5 |
C3—C4—H4 | 127.2 | H16A—C16—H16C | 109.5 |
C5—C4—H4 | 127.2 | H16B—C16—H16C | 109.5 |
N1—C5—C4 | 110.7 (3) | C11—N17—H17B | 115 (3) |
N1—C5—C6 | 121.7 (3) | C11—N17—H17A | 117 (3) |
C4—C5—C6 | 127.4 (3) | H17B—N17—H17A | 109 (4) |
C5—C6—C7 | 116.9 (2) | O18—C19—H19A | 109.5 |
C5—C6—H6A | 108.1 | O18—C19—H19B | 109.5 |
C7—C6—H6A | 108.1 | H19A—C19—H19B | 109.5 |
C5—C6—H6B | 108.1 | O18—C19—H19C | 109.5 |
C7—C6—H6B | 108.1 | H19A—C19—H19C | 109.5 |
H6A—C6—H6B | 107.3 | H19B—C19—H19C | 109.5 |
O8—C7—C9 | 119.8 (3) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N17i | 0.86 | 2.12 | 2.979 (4) | 177 |
N17—H17B···Cl2 | 0.89 (2) | 2.57 (3) | 3.351 (3) | 147 (3) |
N17—H17A···Cl2ii | 0.86 (2) | 2.56 (2) | 3.406 (3) | 169 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1. |