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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055887/hy2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055887/hy2038Isup2.hkl
Contains datablock I

CCDC reference: 636697

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.027
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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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

Computing details top

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]-1H-pyrazol- 5-olato-κ2O,N4}nickel(II) dimethyl sulfoxide disolvate top
Crystal data top
[Ni(C23H18N3O)2(H2O)2]·2C2H6OSF(000) = 2008
Mr = 955.86Dx = 1.357 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6169 reflections
a = 24.399 (1) Åθ = 1.9–29.9°
b = 11.9075 (6) ŵ = 0.56 mm1
c = 16.8717 (8) ÅT = 120 K
β = 107.421 (1)°Prism, blue–green
V = 4677.0 (4) Å30.60 × 0.50 × 0.30 mm
Z = 4
Data collection top
Siemens SMART CCD
diffractometer
6483 independent reflections
Radiation source: sealed X-ray tube5096 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 29.9°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2134
Tmin = 0.634, Tmax = 0.837k = 1616
20050 measured reflectionsl = 2320
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.030H 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 reflectionsΔρmax = 0.20 (3) e Å3
302 parametersΔρmin = 0.17 (3) e Å3
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
xyzUiso*/Ueq
Ni0.000000.45819 (3)0.250000.0132 (1)
O80.05047 (4)0.47130 (9)0.32463 (6)0.0160 (6)
O600.05240 (5)0.58774 (10)0.31712 (7)0.0188 (7)
N10.05092 (5)0.3350 (1)0.32830 (8)0.0157 (7)
N50.05285 (6)0.3700 (1)0.51821 (8)0.0168 (7)
N60.07513 (5)0.4309 (1)0.44483 (7)0.0153 (7)
C20.04520 (6)0.2977 (1)0.39820 (9)0.0151 (8)
C30.00303 (6)0.3424 (1)0.43338 (9)0.0151 (8)
C40.00668 (6)0.3185 (1)0.51117 (9)0.0159 (8)
C70.04100 (6)0.4194 (1)0.39261 (9)0.0144 (8)
C90.02852 (7)0.2537 (2)0.58529 (10)0.0229 (9)
C200.12995 (6)0.4808 (1)0.42919 (9)0.0156 (8)
C210.15538 (7)0.5406 (1)0.35664 (9)0.0203 (8)
C220.21059 (7)0.5829 (1)0.34224 (10)0.0234 (9)
C230.24091 (7)0.5684 (1)0.39934 (10)0.0235 (9)
C240.21477 (7)0.5105 (1)0.47217 (10)0.0222 (9)
C250.15994 (7)0.4667 (1)0.48731 (9)0.0189 (8)
C300.09210 (7)0.2839 (1)0.29391 (9)0.0167 (8)
C310.14227 (7)0.3412 (1)0.29681 (10)0.0211 (9)
C320.17837 (7)0.3001 (2)0.25347 (11)0.0253 (10)
C330.16456 (7)0.2026 (2)0.20698 (10)0.0248 (9)
C340.11546 (7)0.1439 (1)0.20586 (10)0.0247 (9)
C350.07935 (7)0.1841 (1)0.24954 (10)0.0216 (9)
C800.08220 (7)0.2041 (1)0.44526 (9)0.0171 (8)
C810.13887 (7)0.2249 (1)0.49097 (10)0.0212 (9)
C820.17171 (7)0.1406 (2)0.53980 (10)0.0263 (10)
C830.14828 (8)0.0354 (2)0.54231 (11)0.0301 (10)
C840.09216 (9)0.0135 (1)0.49547 (12)0.0297 (11)
C850.05907 (7)0.0975 (1)0.44725 (10)0.0232 (9)
O900.17124 (5)0.6300 (1)0.33361 (8)0.0290 (7)
S910.19396 (2)0.74776 (4)0.34885 (3)0.0249 (2)
C920.16580 (10)0.8067 (2)0.42515 (14)0.0471 (15)
C930.15445 (12)0.8293 (2)0.26301 (15)0.0552 (16)
H60a0.0543 (8)0.593 (2)0.367 (1)0.032 (6)*
H60b0.0861 (10)0.593 (2)0.317 (1)0.043 (7)*
H9a0.023550.28470.634580.0274*
H9b0.067960.25700.588100.0274*
H9c0.015770.17800.579260.0274*
H210.135150.55240.317220.0244*
H220.228020.62260.292190.0281*
H230.278670.59760.388720.0282*
H240.234690.50070.512200.0266*
H250.142670.42690.537390.0227*
H310.151900.40830.328350.0253*
H320.212740.33930.255770.0304*
H330.188710.17620.176040.0297*
H340.106340.07590.175230.0297*
H350.045830.14320.248980.0259*
H810.155210.29690.488870.0254*
H820.210320.15530.571510.0316*
H830.170670.02190.576160.0361*
H840.076340.05930.496410.0356*
H850.020530.08230.415460.0278*
H92a0.180180.88120.434780.0565*
H92b0.178050.76420.474990.0565*
H92c0.125020.80760.405520.0565*
H93a0.168820.90380.272660.0662*
H93b0.114760.82790.258900.0662*
H93c0.159670.80080.213170.0662*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0135 (1)0.0161 (1)0.0115 (1)0.00000.0064 (1)0.0000
O80.0157 (5)0.0208 (6)0.0136 (5)0.0023 (4)0.0078 (4)0.0026 (4)
O600.0195 (6)0.0246 (6)0.0141 (6)0.0028 (5)0.0080 (5)0.0040 (5)
N10.0155 (6)0.0183 (6)0.0149 (6)0.0019 (5)0.0071 (5)0.0009 (5)
N50.0181 (6)0.0205 (7)0.0126 (6)0.0025 (5)0.0057 (5)0.0027 (5)
N60.0160 (6)0.0191 (7)0.0122 (6)0.0028 (5)0.0065 (5)0.0021 (5)
C20.0147 (7)0.0158 (7)0.0152 (7)0.0006 (6)0.0049 (6)0.0016 (6)
C30.0161 (7)0.0168 (7)0.0139 (7)0.0007 (6)0.0065 (6)0.0002 (6)
C40.0166 (7)0.0179 (7)0.0140 (7)0.0009 (6)0.0057 (6)0.0000 (6)
C70.0129 (7)0.0174 (7)0.0138 (7)0.0022 (6)0.0055 (6)0.0033 (6)
C90.0249 (9)0.0305 (9)0.0155 (7)0.0083 (8)0.0097 (6)0.0050 (7)
C200.0141 (7)0.0173 (8)0.0167 (7)0.0006 (6)0.0065 (6)0.0021 (6)
C210.0195 (8)0.0264 (8)0.0174 (7)0.0031 (7)0.0091 (6)0.0020 (7)
C220.0212 (8)0.0292 (9)0.0199 (8)0.0063 (7)0.0059 (7)0.0043 (7)
C230.0152 (7)0.0291 (9)0.0273 (9)0.0042 (7)0.0084 (7)0.0001 (7)
C240.0203 (8)0.0267 (9)0.0242 (8)0.0002 (7)0.0138 (7)0.0010 (7)
C250.0186 (7)0.0222 (8)0.0178 (7)0.0018 (7)0.0084 (6)0.0019 (7)
C300.0174 (8)0.0203 (8)0.0143 (7)0.0048 (6)0.0075 (6)0.0033 (6)
C310.0187 (8)0.0223 (8)0.0242 (8)0.0019 (7)0.0091 (7)0.0000 (7)
C320.0179 (8)0.0299 (9)0.0318 (9)0.0034 (7)0.0130 (7)0.0049 (8)
C330.0224 (8)0.0350 (10)0.0203 (8)0.0106 (7)0.0115 (7)0.0022 (7)
C340.0243 (9)0.0283 (9)0.0217 (8)0.0061 (7)0.0072 (7)0.0053 (7)
C350.0189 (8)0.0236 (8)0.0241 (8)0.0010 (7)0.0093 (7)0.0023 (7)
C800.0205 (8)0.0194 (7)0.0147 (7)0.0048 (6)0.0102 (6)0.0017 (6)
C810.0225 (8)0.0228 (8)0.0200 (8)0.0038 (7)0.0089 (7)0.0006 (6)
C820.0250 (9)0.0351 (10)0.0196 (8)0.0114 (8)0.0076 (7)0.0024 (7)
C830.0386 (10)0.0307 (9)0.0257 (9)0.0187 (9)0.0168 (8)0.0094 (8)
C840.0427 (11)0.0194 (9)0.0338 (10)0.0052 (8)0.0218 (9)0.0050 (7)
C850.0249 (9)0.0219 (8)0.0259 (9)0.0013 (7)0.0123 (7)0.0013 (7)
O900.0377 (7)0.0260 (6)0.0293 (7)0.0065 (6)0.0190 (6)0.0067 (5)
S910.0243 (2)0.0278 (2)0.0252 (2)0.0053 (2)0.0115 (2)0.0040 (2)
C920.0658 (15)0.0355 (12)0.0547 (14)0.0158 (11)0.0402 (13)0.0207 (10)
C930.0736 (17)0.0366 (13)0.0434 (13)0.0006 (12)0.0006 (12)0.0047 (10)
Geometric parameters (Å, º) top
Ni—O82.014 (1)C83—C841.385 (3)
Ni—O602.105 (1)C84—C851.386 (2)
Ni—N12.111 (1)O90—S911.501 (1)
N1—C21.306 (2)S91—C931.770 (2)
O8—C71.262 (2)S91—C921.775 (2)
N1—C301.438 (2)O60—H60a0.83 (2)
N5—C41.319 (2)O60—H60b0.82 (2)
N5—N61.397 (2)C9—H9a0.950
N6—C71.388 (2)C9—H9b0.950
N6—C201.414 (2)C9—H9c0.950
C2—C31.435 (2)C21—H210.950
C2—C801.503 (2)C22—H220.950
C3—C71.423 (2)C23—H230.950
C3—C41.430 (2)C24—H240.950
C4—C91.501 (2)C25—H250.950
C20—C211.391 (2)C31—H310.950
C20—C251.398 (2)C32—H320.950
C21—C221.390 (2)C33—H330.950
C22—C231.390 (2)C34—H340.950
C23—C241.387 (2)C35—H350.950
C24—C251.387 (2)C81—H810.950
C30—C351.389 (2)C82—H820.950
C30—C311.390 (2)C83—H830.950
C31—C321.391 (2)C84—H840.950
C32—C331.386 (2)C85—H850.950
C33—C341.383 (2)C92—H92a0.950
C34—C351.392 (2)C92—H92b0.950
C80—C811.389 (2)C92—H92c0.950
C80—C851.394 (2)C93—H93a0.950
C81—C821.390 (2)C93—H93b0.950
C82—C831.383 (3)C93—H93c0.950
O8—Ni—O8i171.11 (6)O90—S91—C92106.87 (8)
O8—Ni—O6089.62 (4)C92—S91—C9398.2 (1)
O8—Ni—O60i83.85 (4)Ni—O60—H60a116 (1)
O8—Ni—N191.04 (4)Ni—O60—H60b120 (1)
O8—Ni—N1i95.14 (4)H60a—O60—H60b104 (2)
O60—Ni—O60i85.73 (7)H9a—C9—H9b109.5
O60—Ni—N191.35 (5)H9a—C9—H9c109.8
O60—Ni—N1i174.12 (5)C4—C9—H9a109.8
N1—Ni—N1i92.00 (7)H9b—C9—H9c109.8
Ni—O8—C7123.41 (9)C4—C9—H9b109.8
Ni—N1—C2126.8 (1)C4—C9—H9c108.2
Ni—N1—C30113.17 (9)C22—C21—H21120.2
C2—N1—C30119.8 (1)C20—C21—H21120.2
N6—N5—C4106.1 (1)C21—C22—H22119.2
N5—N6—C7111.3 (1)C23—C22—H22119.2
C7—N6—C20129.5 (1)C24—C23—H23120.8
N5—N6—C20118.6 (1)C22—C23—H23120.8
N1—C2—C3122.1 (1)C23—C24—H24119.6
N1—C2—C80121.3 (1)C25—C24—H24119.6
C3—C2—C80116.6 (1)C24—C25—H25119.9
C4—C3—C7105.2 (1)C20—C25—H25119.9
C2—C3—C7124.7 (1)C30—C31—H31120.1
C2—C3—C4130.0 (1)C32—C31—H31120.0
N5—C4—C3111.8 (1)C33—C32—H32119.8
N5—C4—C9117.1 (1)C31—C32—H32119.8
C3—C4—C9131.0 (1)C34—C33—H33120.2
O8—C7—N6123.2 (1)C32—C33—H33120.2
O8—C7—C3131.4 (1)C33—C34—H34119.9
N6—C7—C3105.4 (1)C35—C34—H34119.9
C21—C20—C25119.3 (1)C30—C35—H35119.8
N6—C20—C21121.8 (1)C34—C35—H35119.8
N6—C20—C25118.9 (1)C80—C81—H81120.0
C20—C21—C22119.5 (1)C82—C81—H81120.0
C21—C22—C23121.5 (1)C83—C82—H82119.9
C22—C23—C24118.5 (1)C81—C82—H82119.9
C23—C24—C25120.8 (1)C82—C83—H83120.0
C20—C25—C24120.3 (1)C84—C83—H83120.0
C31—C30—C35119.5 (1)C83—C84—H84120.0
N1—C30—C35120.6 (1)C85—C84—H84120.0
N1—C30—C31119.5 (1)C84—C85—H85119.9
C30—C31—C32119.9 (2)C80—C85—H85119.9
C31—C32—C33120.5 (2)H92a—C92—H92b110.1
C32—C33—C34119.6 (1)H92a—C92—H92c110.1
C33—C34—C35120.1 (2)S91—C92—H92a106.9
C30—C35—C34120.3 (1)H92b—C92—H92c109.5
C81—C80—C85119.5 (1)S91—C92—H92b110.1
C2—C80—C81120.1 (1)S91—C92—H92c110.1
C2—C80—C85120.3 (1)H93a—C93—H93b110.1
C80—C81—C82120.1 (2)H93a—C93—H93c110.1
C81—C82—C83120.1 (2)S91—C93—H93a106.8
C82—C83—C84120.0 (2)H93b—C93—H93c109.5
C83—C84—C85120.1 (2)S91—C93—H93b110.1
C80—C85—C84120.2 (2)S91—C93—H93c110.1
O90—S91—C93106.8 (1)
N5—N6—C20—C21178.6 (2)Ni—N1—C30—C3178.0 (2)
N5—N6—C20—C250.5 (3)Ni—N1—C30—C3594.5 (1)
C7—N6—C20—C218.1 (2)C3—C2—C80—C81104.8 (2)
C7—N6—C20—C25170.0 (1)C3—C2—C80—C8571.6 (2)
C2—N1—C30—C31107.1 (2)N1—C2—C80—C8176.1 (2)
C2—N1—C30—C3580.4 (2)N1—C2—C80—C85107.6 (2)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O60—H60a···N5ii0.83 (2)2.00 (2)2.820 (2)171 (2)
O60—H60b···O900.82 (2)2.06 (2)2.873 (2)168 (2)
Symmetry code: (ii) x, y+1, z+1.
 

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