In the title compound, [Ni(C23H18N3O)2(H2O)2]·2C2H6OS, the Ni atom is octahedrally coordinated by two N atoms and two O atoms from two organic ligands and two water molecules which are cis to each other. The complex has crystallographic twofold rotation symmetry.
Supporting information
CCDC reference: 636697
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.030
- wR factor = 0.027
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S91
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 45.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: KRYSTAL (Hazell, 1995); molecular graphics: KRYSTAL; software used to prepare material for publication: KRYSTAL.
Diaquabis{3-methyl-1-phenyl-4-[(
E)-phenyl(phenyliminio)methyl]-1
H-pyrazol- 5-olato-
κ2O,
N4}nickel(II) dimethyl
sulfoxide disolvate
top
Crystal data top
[Ni(C23H18N3O)2(H2O)2]·2C2H6OS | F(000) = 2008 |
Mr = 955.86 | Dx = 1.357 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6169 reflections |
a = 24.399 (1) Å | θ = 1.9–29.9° |
b = 11.9075 (6) Å | µ = 0.56 mm−1 |
c = 16.8717 (8) Å | T = 120 K |
β = 107.421 (1)° | Prism, blue–green |
V = 4677.0 (4) Å3 | 0.60 × 0.50 × 0.30 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD diffractometer | 6483 independent reflections |
Radiation source: sealed X-ray tube | 5096 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 29.9°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→34 |
Tmin = 0.634, Tmax = 0.837 | k = −16→16 |
20050 measured reflections | l = −23→20 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.027 | w = 1/{[σcs(F2) + B + (1 + A)F2]1/2-|F|}2, where A = 0.012 and B = 1.0 |
S = 1.01 | (Δ/σ)max = 0.001 |
5096 reflections | Δρmax = 0.20 (3) e Å−3 |
302 parameters | Δρmin = −0.17 (3) e Å−3 |
Special details top
Refinement. Sfls: F calc weight full matrix Hydrogen atoms of the ligands and solvent were kept fixed with C—H = 0.95 A
and Uiso = 1.2Ueq for the atom to which H is bonded. H atoms of the
water molecules were obtained from a difference map and refined isotropically |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni | 0.00000 | 0.45819 (3) | 0.25000 | 0.0132 (1) | |
O8 | −0.05047 (4) | 0.47130 (9) | 0.32463 (6) | 0.0160 (6) | |
O60 | 0.05240 (5) | 0.58774 (10) | 0.31712 (7) | 0.0188 (7) | |
N1 | 0.05092 (5) | 0.3350 (1) | 0.32830 (8) | 0.0157 (7) | |
N5 | −0.05285 (6) | 0.3700 (1) | 0.51821 (8) | 0.0168 (7) | |
N6 | −0.07513 (5) | 0.4309 (1) | 0.44483 (7) | 0.0153 (7) | |
C2 | 0.04520 (6) | 0.2977 (1) | 0.39820 (9) | 0.0151 (8) | |
C3 | 0.00303 (6) | 0.3424 (1) | 0.43338 (9) | 0.0151 (8) | |
C4 | −0.00668 (6) | 0.3185 (1) | 0.51117 (9) | 0.0159 (8) | |
C7 | −0.04100 (6) | 0.4194 (1) | 0.39261 (9) | 0.0144 (8) | |
C9 | 0.02852 (7) | 0.2537 (2) | 0.58529 (10) | 0.0229 (9) | |
C20 | −0.12995 (6) | 0.4808 (1) | 0.42919 (9) | 0.0156 (8) | |
C21 | −0.15538 (7) | 0.5406 (1) | 0.35664 (9) | 0.0203 (8) | |
C22 | −0.21059 (7) | 0.5829 (1) | 0.34224 (10) | 0.0234 (9) | |
C23 | −0.24091 (7) | 0.5684 (1) | 0.39934 (10) | 0.0235 (9) | |
C24 | −0.21477 (7) | 0.5105 (1) | 0.47217 (10) | 0.0222 (9) | |
C25 | −0.15994 (7) | 0.4667 (1) | 0.48731 (9) | 0.0189 (8) | |
C30 | 0.09210 (7) | 0.2839 (1) | 0.29391 (9) | 0.0167 (8) | |
C31 | 0.14227 (7) | 0.3412 (1) | 0.29681 (10) | 0.0211 (9) | |
C32 | 0.17837 (7) | 0.3001 (2) | 0.25347 (11) | 0.0253 (10) | |
C33 | 0.16456 (7) | 0.2026 (2) | 0.20698 (10) | 0.0248 (9) | |
C34 | 0.11546 (7) | 0.1439 (1) | 0.20586 (10) | 0.0247 (9) | |
C35 | 0.07935 (7) | 0.1841 (1) | 0.24954 (10) | 0.0216 (9) | |
C80 | 0.08220 (7) | 0.2041 (1) | 0.44526 (9) | 0.0171 (8) | |
C81 | 0.13887 (7) | 0.2249 (1) | 0.49097 (10) | 0.0212 (9) | |
C82 | 0.17171 (7) | 0.1406 (2) | 0.53980 (10) | 0.0263 (10) | |
C83 | 0.14828 (8) | 0.0354 (2) | 0.54231 (11) | 0.0301 (10) | |
C84 | 0.09216 (9) | 0.0135 (1) | 0.49547 (12) | 0.0297 (11) | |
C85 | 0.05907 (7) | 0.0975 (1) | 0.44725 (10) | 0.0232 (9) | |
O90 | 0.17124 (5) | 0.6300 (1) | 0.33361 (8) | 0.0290 (7) | |
S91 | 0.19396 (2) | 0.74776 (4) | 0.34885 (3) | 0.0249 (2) | |
C92 | 0.16580 (10) | 0.8067 (2) | 0.42515 (14) | 0.0471 (15) | |
C93 | 0.15445 (12) | 0.8293 (2) | 0.26301 (15) | 0.0552 (16) | |
H60a | 0.0543 (8) | 0.593 (2) | 0.367 (1) | 0.032 (6)* | |
H60b | 0.0861 (10) | 0.593 (2) | 0.317 (1) | 0.043 (7)* | |
H9a | 0.02355 | 0.2847 | 0.63458 | 0.0274* | |
H9b | 0.06796 | 0.2570 | 0.58810 | 0.0274* | |
H9c | 0.01577 | 0.1780 | 0.57926 | 0.0274* | |
H21 | −0.13515 | 0.5524 | 0.31722 | 0.0244* | |
H22 | −0.22802 | 0.6226 | 0.29219 | 0.0281* | |
H23 | −0.27867 | 0.5976 | 0.38872 | 0.0282* | |
H24 | −0.23469 | 0.5007 | 0.51220 | 0.0266* | |
H25 | −0.14267 | 0.4269 | 0.53739 | 0.0227* | |
H31 | 0.15190 | 0.4083 | 0.32835 | 0.0253* | |
H32 | 0.21274 | 0.3393 | 0.25577 | 0.0304* | |
H33 | 0.18871 | 0.1762 | 0.17604 | 0.0297* | |
H34 | 0.10634 | 0.0759 | 0.17523 | 0.0297* | |
H35 | 0.04583 | 0.1432 | 0.24898 | 0.0259* | |
H81 | 0.15521 | 0.2969 | 0.48887 | 0.0254* | |
H82 | 0.21032 | 0.1553 | 0.57151 | 0.0316* | |
H83 | 0.17067 | −0.0219 | 0.57616 | 0.0361* | |
H84 | 0.07634 | −0.0593 | 0.49641 | 0.0356* | |
H85 | 0.02053 | 0.0823 | 0.41546 | 0.0278* | |
H92a | 0.18018 | 0.8812 | 0.43478 | 0.0565* | |
H92b | 0.17805 | 0.7642 | 0.47499 | 0.0565* | |
H92c | 0.12502 | 0.8076 | 0.40552 | 0.0565* | |
H93a | 0.16882 | 0.9038 | 0.27266 | 0.0662* | |
H93b | 0.11476 | 0.8279 | 0.25890 | 0.0662* | |
H93c | 0.15967 | 0.8008 | 0.21317 | 0.0662* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.0135 (1) | 0.0161 (1) | 0.0115 (1) | 0.0000 | 0.0064 (1) | 0.0000 |
O8 | 0.0157 (5) | 0.0208 (6) | 0.0136 (5) | 0.0023 (4) | 0.0078 (4) | 0.0026 (4) |
O60 | 0.0195 (6) | 0.0246 (6) | 0.0141 (6) | −0.0028 (5) | 0.0080 (5) | −0.0040 (5) |
N1 | 0.0155 (6) | 0.0183 (6) | 0.0149 (6) | 0.0019 (5) | 0.0071 (5) | −0.0009 (5) |
N5 | 0.0181 (6) | 0.0205 (7) | 0.0126 (6) | 0.0025 (5) | 0.0057 (5) | 0.0027 (5) |
N6 | 0.0160 (6) | 0.0191 (7) | 0.0122 (6) | 0.0028 (5) | 0.0065 (5) | 0.0021 (5) |
C2 | 0.0147 (7) | 0.0158 (7) | 0.0152 (7) | −0.0006 (6) | 0.0049 (6) | −0.0016 (6) |
C3 | 0.0161 (7) | 0.0168 (7) | 0.0139 (7) | 0.0007 (6) | 0.0065 (6) | −0.0002 (6) |
C4 | 0.0166 (7) | 0.0179 (7) | 0.0140 (7) | 0.0009 (6) | 0.0057 (6) | 0.0000 (6) |
C7 | 0.0129 (7) | 0.0174 (7) | 0.0138 (7) | −0.0022 (6) | 0.0055 (6) | −0.0033 (6) |
C9 | 0.0249 (9) | 0.0305 (9) | 0.0155 (7) | 0.0083 (8) | 0.0097 (6) | 0.0050 (7) |
C20 | 0.0141 (7) | 0.0173 (8) | 0.0167 (7) | 0.0006 (6) | 0.0065 (6) | −0.0021 (6) |
C21 | 0.0195 (8) | 0.0264 (8) | 0.0174 (7) | 0.0031 (7) | 0.0091 (6) | 0.0020 (7) |
C22 | 0.0212 (8) | 0.0292 (9) | 0.0199 (8) | 0.0063 (7) | 0.0059 (7) | 0.0043 (7) |
C23 | 0.0152 (7) | 0.0291 (9) | 0.0273 (9) | 0.0042 (7) | 0.0084 (7) | 0.0001 (7) |
C24 | 0.0203 (8) | 0.0267 (9) | 0.0242 (8) | 0.0002 (7) | 0.0138 (7) | 0.0010 (7) |
C25 | 0.0186 (7) | 0.0222 (8) | 0.0178 (7) | 0.0018 (7) | 0.0084 (6) | 0.0019 (7) |
C30 | 0.0174 (8) | 0.0203 (8) | 0.0143 (7) | 0.0048 (6) | 0.0075 (6) | 0.0033 (6) |
C31 | 0.0187 (8) | 0.0223 (8) | 0.0242 (8) | 0.0019 (7) | 0.0091 (7) | 0.0000 (7) |
C32 | 0.0179 (8) | 0.0299 (9) | 0.0318 (9) | 0.0034 (7) | 0.0130 (7) | 0.0049 (8) |
C33 | 0.0224 (8) | 0.0350 (10) | 0.0203 (8) | 0.0106 (7) | 0.0115 (7) | 0.0022 (7) |
C34 | 0.0243 (9) | 0.0283 (9) | 0.0217 (8) | 0.0061 (7) | 0.0072 (7) | −0.0053 (7) |
C35 | 0.0189 (8) | 0.0236 (8) | 0.0241 (8) | 0.0010 (7) | 0.0093 (7) | −0.0023 (7) |
C80 | 0.0205 (8) | 0.0194 (7) | 0.0147 (7) | 0.0048 (6) | 0.0102 (6) | 0.0017 (6) |
C81 | 0.0225 (8) | 0.0228 (8) | 0.0200 (8) | 0.0038 (7) | 0.0089 (7) | 0.0006 (6) |
C82 | 0.0250 (9) | 0.0351 (10) | 0.0196 (8) | 0.0114 (8) | 0.0076 (7) | 0.0024 (7) |
C83 | 0.0386 (10) | 0.0307 (9) | 0.0257 (9) | 0.0187 (9) | 0.0168 (8) | 0.0094 (8) |
C84 | 0.0427 (11) | 0.0194 (9) | 0.0338 (10) | 0.0052 (8) | 0.0218 (9) | 0.0050 (7) |
C85 | 0.0249 (9) | 0.0219 (8) | 0.0259 (9) | 0.0013 (7) | 0.0123 (7) | 0.0013 (7) |
O90 | 0.0377 (7) | 0.0260 (6) | 0.0293 (7) | −0.0065 (6) | 0.0190 (6) | −0.0067 (5) |
S91 | 0.0243 (2) | 0.0278 (2) | 0.0252 (2) | −0.0053 (2) | 0.0115 (2) | −0.0040 (2) |
C92 | 0.0658 (15) | 0.0355 (12) | 0.0547 (14) | −0.0158 (11) | 0.0402 (13) | −0.0207 (10) |
C93 | 0.0736 (17) | 0.0366 (13) | 0.0434 (13) | 0.0006 (12) | −0.0006 (12) | 0.0047 (10) |
Geometric parameters (Å, º) top
Ni—O8 | 2.014 (1) | C83—C84 | 1.385 (3) |
Ni—O60 | 2.105 (1) | C84—C85 | 1.386 (2) |
Ni—N1 | 2.111 (1) | O90—S91 | 1.501 (1) |
N1—C2 | 1.306 (2) | S91—C93 | 1.770 (2) |
O8—C7 | 1.262 (2) | S91—C92 | 1.775 (2) |
N1—C30 | 1.438 (2) | O60—H60a | 0.83 (2) |
N5—C4 | 1.319 (2) | O60—H60b | 0.82 (2) |
N5—N6 | 1.397 (2) | C9—H9a | 0.950 |
N6—C7 | 1.388 (2) | C9—H9b | 0.950 |
N6—C20 | 1.414 (2) | C9—H9c | 0.950 |
C2—C3 | 1.435 (2) | C21—H21 | 0.950 |
C2—C80 | 1.503 (2) | C22—H22 | 0.950 |
C3—C7 | 1.423 (2) | C23—H23 | 0.950 |
C3—C4 | 1.430 (2) | C24—H24 | 0.950 |
C4—C9 | 1.501 (2) | C25—H25 | 0.950 |
C20—C21 | 1.391 (2) | C31—H31 | 0.950 |
C20—C25 | 1.398 (2) | C32—H32 | 0.950 |
C21—C22 | 1.390 (2) | C33—H33 | 0.950 |
C22—C23 | 1.390 (2) | C34—H34 | 0.950 |
C23—C24 | 1.387 (2) | C35—H35 | 0.950 |
C24—C25 | 1.387 (2) | C81—H81 | 0.950 |
C30—C35 | 1.389 (2) | C82—H82 | 0.950 |
C30—C31 | 1.390 (2) | C83—H83 | 0.950 |
C31—C32 | 1.391 (2) | C84—H84 | 0.950 |
C32—C33 | 1.386 (2) | C85—H85 | 0.950 |
C33—C34 | 1.383 (2) | C92—H92a | 0.950 |
C34—C35 | 1.392 (2) | C92—H92b | 0.950 |
C80—C81 | 1.389 (2) | C92—H92c | 0.950 |
C80—C85 | 1.394 (2) | C93—H93a | 0.950 |
C81—C82 | 1.390 (2) | C93—H93b | 0.950 |
C82—C83 | 1.383 (3) | C93—H93c | 0.950 |
| | | |
O8—Ni—O8i | 171.11 (6) | O90—S91—C92 | 106.87 (8) |
O8—Ni—O60 | 89.62 (4) | C92—S91—C93 | 98.2 (1) |
O8—Ni—O60i | 83.85 (4) | Ni—O60—H60a | 116 (1) |
O8—Ni—N1 | 91.04 (4) | Ni—O60—H60b | 120 (1) |
O8—Ni—N1i | 95.14 (4) | H60a—O60—H60b | 104 (2) |
O60—Ni—O60i | 85.73 (7) | H9a—C9—H9b | 109.5 |
O60—Ni—N1 | 91.35 (5) | H9a—C9—H9c | 109.8 |
O60—Ni—N1i | 174.12 (5) | C4—C9—H9a | 109.8 |
N1—Ni—N1i | 92.00 (7) | H9b—C9—H9c | 109.8 |
Ni—O8—C7 | 123.41 (9) | C4—C9—H9b | 109.8 |
Ni—N1—C2 | 126.8 (1) | C4—C9—H9c | 108.2 |
Ni—N1—C30 | 113.17 (9) | C22—C21—H21 | 120.2 |
C2—N1—C30 | 119.8 (1) | C20—C21—H21 | 120.2 |
N6—N5—C4 | 106.1 (1) | C21—C22—H22 | 119.2 |
N5—N6—C7 | 111.3 (1) | C23—C22—H22 | 119.2 |
C7—N6—C20 | 129.5 (1) | C24—C23—H23 | 120.8 |
N5—N6—C20 | 118.6 (1) | C22—C23—H23 | 120.8 |
N1—C2—C3 | 122.1 (1) | C23—C24—H24 | 119.6 |
N1—C2—C80 | 121.3 (1) | C25—C24—H24 | 119.6 |
C3—C2—C80 | 116.6 (1) | C24—C25—H25 | 119.9 |
C4—C3—C7 | 105.2 (1) | C20—C25—H25 | 119.9 |
C2—C3—C7 | 124.7 (1) | C30—C31—H31 | 120.1 |
C2—C3—C4 | 130.0 (1) | C32—C31—H31 | 120.0 |
N5—C4—C3 | 111.8 (1) | C33—C32—H32 | 119.8 |
N5—C4—C9 | 117.1 (1) | C31—C32—H32 | 119.8 |
C3—C4—C9 | 131.0 (1) | C34—C33—H33 | 120.2 |
O8—C7—N6 | 123.2 (1) | C32—C33—H33 | 120.2 |
O8—C7—C3 | 131.4 (1) | C33—C34—H34 | 119.9 |
N6—C7—C3 | 105.4 (1) | C35—C34—H34 | 119.9 |
C21—C20—C25 | 119.3 (1) | C30—C35—H35 | 119.8 |
N6—C20—C21 | 121.8 (1) | C34—C35—H35 | 119.8 |
N6—C20—C25 | 118.9 (1) | C80—C81—H81 | 120.0 |
C20—C21—C22 | 119.5 (1) | C82—C81—H81 | 120.0 |
C21—C22—C23 | 121.5 (1) | C83—C82—H82 | 119.9 |
C22—C23—C24 | 118.5 (1) | C81—C82—H82 | 119.9 |
C23—C24—C25 | 120.8 (1) | C82—C83—H83 | 120.0 |
C20—C25—C24 | 120.3 (1) | C84—C83—H83 | 120.0 |
C31—C30—C35 | 119.5 (1) | C83—C84—H84 | 120.0 |
N1—C30—C35 | 120.6 (1) | C85—C84—H84 | 120.0 |
N1—C30—C31 | 119.5 (1) | C84—C85—H85 | 119.9 |
C30—C31—C32 | 119.9 (2) | C80—C85—H85 | 119.9 |
C31—C32—C33 | 120.5 (2) | H92a—C92—H92b | 110.1 |
C32—C33—C34 | 119.6 (1) | H92a—C92—H92c | 110.1 |
C33—C34—C35 | 120.1 (2) | S91—C92—H92a | 106.9 |
C30—C35—C34 | 120.3 (1) | H92b—C92—H92c | 109.5 |
C81—C80—C85 | 119.5 (1) | S91—C92—H92b | 110.1 |
C2—C80—C81 | 120.1 (1) | S91—C92—H92c | 110.1 |
C2—C80—C85 | 120.3 (1) | H93a—C93—H93b | 110.1 |
C80—C81—C82 | 120.1 (2) | H93a—C93—H93c | 110.1 |
C81—C82—C83 | 120.1 (2) | S91—C93—H93a | 106.8 |
C82—C83—C84 | 120.0 (2) | H93b—C93—H93c | 109.5 |
C83—C84—C85 | 120.1 (2) | S91—C93—H93b | 110.1 |
C80—C85—C84 | 120.2 (2) | S91—C93—H93c | 110.1 |
O90—S91—C93 | 106.8 (1) | | |
| | | |
N5—N6—C20—C21 | −178.6 (2) | Ni—N1—C30—C31 | 78.0 (2) |
N5—N6—C20—C25 | −0.5 (3) | Ni—N1—C30—C35 | −94.5 (1) |
C7—N6—C20—C21 | −8.1 (2) | C3—C2—C80—C81 | −104.8 (2) |
C7—N6—C20—C25 | 170.0 (1) | C3—C2—C80—C85 | 71.6 (2) |
C2—N1—C30—C31 | −107.1 (2) | N1—C2—C80—C81 | 76.1 (2) |
C2—N1—C30—C35 | 80.4 (2) | N1—C2—C80—C85 | −107.6 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O60—H60a···N5ii | 0.83 (2) | 2.00 (2) | 2.820 (2) | 171 (2) |
O60—H60b···O90 | 0.82 (2) | 2.06 (2) | 2.873 (2) | 168 (2) |
Symmetry code: (ii) −x, −y+1, −z+1. |