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The title compound, C18H15Cl2N3O2, was derived from the product of the intermolecular [3 + 2]-cyclo­addition reaction of 2,6-di­chloro­benzo­nitrile oxide and 1,5-di­methyl-2-phenyl-1,2-di­hydro­pyrazol-3-one. The hydroxy group and the 2,6-di­chloro­phenyl ring of the oxime are in a trans conformation and the C=N—O angle is 113.90 (15) Å. Pairs of mol­ecules form centrosymmetric O—H...N hydrogen-bonded dimers, with an O...N distance of 2.821 (2) Å. The pyrazole ring is nearly planar, with a mean deviation from the plane of 0.0246 (3) Å and a dihedral angle between the pyrazole and the unsubstituted phenyl ring of 131.7 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002423/lh6031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002423/lh6031Isup2.hkl
Contains datablock I

CCDC reference: 206754

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.090
  • Data-to-parameter ratio = 13.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.746 0.940 Tmin' and Tmax expected: 0.876 0.940 RR' = 0.852 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

4-[(2,6-Dichlorophenyl)(hydroxyimino)methyl]-1,5-dimethyl-2-phenyl-1,2- dihydropyrazol-3-one top
Crystal data top
C18H15Cl2N3O2Z = 2
Mr = 376.23F(000) = 388
Triclinic, P1Dx = 1.414 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.804 (2) ÅCell parameters from 985 reflections
b = 9.123 (4) Åθ = 2.5–26.4°
c = 13.523 (5) ŵ = 0.38 mm1
α = 74.313 (8)°T = 293 K
β = 78.473 (8)°Plate, colorless
γ = 74.265 (8)°0.34 × 0.20 × 0.16 mm
V = 883.7 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3028 independent reflections
Radiation source: fine-focus sealed tube2537 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 69
Tmin = 0.746, Tmax = 0.940k = 1010
6966 measured reflectionsl = 1616
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.035(Δ/σ)max < 0.001
wR(F2) = 0.090Δρmax = 0.21 e Å3
S = 1.02Δρmin = 0.28 e Å3
3028 reflectionsExtinction correction: SHELXL
230 parametersExtinction coefficient: 0.008 (2)
0 restraints
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
Cl10.30810 (8)0.54729 (7)0.29345 (5)0.0602 (2)
Cl20.92190 (8)0.15995 (8)0.41724 (5)0.0709 (2)
N10.6922 (2)0.27921 (19)0.04572 (11)0.0357 (4)
N20.5384 (2)0.2195 (2)0.06355 (12)0.0399 (4)
N30.5301 (2)0.12883 (19)0.40513 (12)0.0430 (4)
O10.86380 (18)0.32516 (17)0.15013 (10)0.0415 (3)
O20.4977 (3)0.00093 (17)0.37946 (11)0.0605 (5)
H20.47730.06450.43260.091*
C10.8273 (2)0.2454 (2)0.03810 (13)0.0327 (4)
C20.9414 (3)0.3454 (2)0.08070 (14)0.0382 (4)
H2A0.92690.43490.05660.046*
C31.0773 (3)0.3108 (3)0.15941 (15)0.0459 (5)
H31.15560.37690.18780.055*
C41.0981 (3)0.1794 (3)0.19630 (16)0.0495 (5)
H41.19060.15640.24900.059*
C50.9818 (3)0.0824 (2)0.15499 (15)0.0450 (5)
H50.99380.00500.18100.054*
C60.8473 (3)0.1138 (2)0.07526 (15)0.0397 (5)
H60.77020.04670.04650.048*
C70.7306 (2)0.2872 (2)0.14110 (13)0.0315 (4)
C80.5865 (2)0.2379 (2)0.21657 (13)0.0326 (4)
C90.4712 (3)0.2068 (2)0.16560 (15)0.0394 (5)
C100.2911 (3)0.1735 (3)0.20529 (19)0.0618 (7)
H10A0.20640.24130.16050.093*
H10B0.25400.19120.27400.093*
H10C0.29630.06650.20700.093*
C110.4269 (3)0.2753 (3)0.01974 (17)0.0542 (6)
H11A0.33320.21940.00390.081*
H11B0.49960.25810.08360.081*
H11C0.37460.38510.02660.081*
C120.5729 (2)0.2333 (2)0.32670 (14)0.0336 (4)
C130.6191 (2)0.3626 (2)0.35570 (12)0.0314 (4)
C140.5069 (3)0.5118 (2)0.34302 (13)0.0375 (4)
C150.5455 (3)0.6320 (2)0.37194 (16)0.0513 (6)
H150.46800.73060.36250.062*
C160.6982 (4)0.6044 (3)0.41445 (17)0.0589 (6)
H160.72420.68440.43510.071*
C170.8140 (3)0.4605 (3)0.42723 (17)0.0562 (6)
H170.91930.44320.45530.067*
C180.7742 (3)0.3411 (2)0.39846 (14)0.0407 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0551 (4)0.0591 (4)0.0571 (4)0.0070 (3)0.0177 (3)0.0110 (3)
Cl20.0509 (4)0.0701 (4)0.0743 (4)0.0048 (3)0.0143 (3)0.0022 (3)
N10.0335 (8)0.0493 (10)0.0295 (8)0.0182 (7)0.0004 (6)0.0121 (7)
N20.0347 (9)0.0552 (11)0.0365 (9)0.0190 (8)0.0028 (7)0.0143 (8)
N30.0636 (11)0.0309 (9)0.0355 (9)0.0197 (8)0.0061 (8)0.0099 (7)
O10.0423 (8)0.0559 (9)0.0349 (7)0.0250 (7)0.0002 (6)0.0145 (6)
O20.1079 (14)0.0401 (9)0.0417 (8)0.0407 (9)0.0074 (9)0.0120 (7)
C10.0345 (10)0.0390 (10)0.0246 (9)0.0093 (8)0.0057 (7)0.0054 (7)
C20.0438 (11)0.0424 (11)0.0323 (10)0.0169 (9)0.0028 (8)0.0098 (8)
C30.0442 (12)0.0594 (14)0.0358 (11)0.0238 (10)0.0038 (9)0.0088 (10)
C40.0444 (12)0.0643 (15)0.0364 (11)0.0096 (11)0.0041 (9)0.0160 (10)
C50.0510 (12)0.0431 (12)0.0404 (11)0.0056 (10)0.0050 (10)0.0151 (9)
C60.0453 (11)0.0378 (11)0.0374 (10)0.0144 (9)0.0052 (9)0.0067 (8)
C70.0355 (10)0.0312 (9)0.0294 (9)0.0097 (8)0.0027 (8)0.0086 (7)
C80.0362 (10)0.0311 (10)0.0315 (9)0.0115 (8)0.0006 (8)0.0088 (8)
C90.0374 (11)0.0431 (11)0.0398 (11)0.0150 (9)0.0028 (8)0.0130 (9)
C100.0451 (13)0.0902 (19)0.0594 (14)0.0352 (13)0.0057 (11)0.0221 (13)
C110.0465 (13)0.0719 (16)0.0505 (13)0.0177 (11)0.0152 (10)0.0140 (11)
C120.0366 (10)0.0309 (10)0.0313 (9)0.0089 (8)0.0035 (8)0.0084 (8)
C130.0393 (10)0.0316 (9)0.0215 (8)0.0125 (8)0.0040 (7)0.0045 (7)
C140.0475 (12)0.0348 (10)0.0259 (9)0.0109 (9)0.0031 (8)0.0045 (8)
C150.0768 (16)0.0335 (11)0.0405 (11)0.0165 (11)0.0094 (11)0.0120 (9)
C160.0863 (18)0.0595 (15)0.0449 (12)0.0416 (14)0.0076 (12)0.0222 (11)
C170.0585 (14)0.0829 (18)0.0399 (12)0.0376 (14)0.0016 (10)0.0173 (12)
C180.0403 (11)0.0476 (12)0.0307 (10)0.0133 (9)0.0019 (8)0.0048 (8)
Geometric parameters (Å, º) top
Cl1—C141.729 (2)C6—H60.9300
Cl2—C181.727 (2)C7—C81.441 (3)
N1—N21.402 (2)C8—C91.362 (3)
N1—C71.405 (2)C8—C121.462 (2)
N1—C11.423 (2)C9—C101.483 (3)
N2—C91.360 (2)C10—H10A0.9600
N2—C111.458 (3)C10—H10B0.9600
N3—C121.276 (2)C10—H10C0.9600
N3—O21.400 (2)C11—H11A0.9600
O1—C71.218 (2)C11—H11B0.9600
O2—H20.8200C11—H11C0.9600
C1—C21.381 (3)C12—C131.487 (2)
C1—C61.383 (3)C13—C181.389 (3)
C2—C31.381 (3)C13—C141.392 (3)
C2—H2A0.9300C14—C151.379 (3)
C3—C41.378 (3)C15—C161.359 (3)
C3—H30.9300C15—H150.9300
C4—C51.373 (3)C16—C171.366 (4)
C4—H40.9300C16—H160.9300
C5—C61.377 (3)C17—C181.376 (3)
C5—H50.9300C17—H170.9300
N2—N1—C7108.85 (14)C8—C9—C10129.14 (18)
N2—N1—C1118.66 (14)C9—C10—H10A109.5
C7—N1—C1123.32 (15)C9—C10—H10B109.5
C9—N2—N1107.48 (14)H10A—C10—H10B109.5
C9—N2—C11123.67 (17)C9—C10—H10C109.5
N1—N2—C11115.69 (16)H10A—C10—H10C109.5
C12—N3—O2113.90 (15)H10B—C10—H10C109.5
N3—O2—H2109.5N2—C11—H11A109.5
C2—C1—C6120.26 (18)N2—C11—H11B109.5
C2—C1—N1118.64 (16)H11A—C11—H11B109.5
C6—C1—N1121.09 (17)N2—C11—H11C109.5
C3—C2—C1119.22 (18)H11A—C11—H11C109.5
C3—C2—H2A120.4H11B—C11—H11C109.5
C1—C2—H2A120.4N3—C12—C8128.76 (17)
C4—C3—C2120.67 (19)N3—C12—C13112.99 (16)
C4—C3—H3119.7C8—C12—C13118.22 (15)
C2—C3—H3119.7C18—C13—C14116.17 (17)
C5—C4—C3119.7 (2)C18—C13—C12122.20 (17)
C5—C4—H4120.1C14—C13—C12121.63 (17)
C3—C4—H4120.1C15—C14—C13122.4 (2)
C4—C5—C6120.3 (2)C15—C14—Cl1118.44 (17)
C4—C5—H5119.8C13—C14—Cl1119.16 (15)
C6—C5—H5119.8C16—C15—C14119.1 (2)
C5—C6—C1119.75 (19)C16—C15—H15120.4
C5—C6—H6120.1C14—C15—H15120.4
C1—C6—H6120.1C15—C16—C17120.8 (2)
O1—C7—N1123.34 (16)C15—C16—H16119.6
O1—C7—C8131.68 (16)C17—C16—H16119.6
N1—C7—C8104.95 (15)C16—C17—C18119.7 (2)
C9—C8—C7108.06 (16)C16—C17—H17120.1
C9—C8—C12129.27 (17)C18—C17—H17120.1
C7—C8—C12122.59 (16)C17—C18—C13121.8 (2)
N2—C9—C8110.17 (16)C17—C18—Cl2118.55 (17)
N2—C9—C10120.57 (18)C13—C18—Cl2119.61 (16)
C7—N1—N2—C96.4 (2)C7—C8—C9—N25.2 (2)
C1—N1—N2—C9154.40 (16)C12—C8—C9—N2177.77 (18)
C7—N1—N2—C11149.20 (17)C7—C8—C9—C10170.8 (2)
C1—N1—N2—C1162.8 (2)C12—C8—C9—C106.3 (4)
N2—N1—C1—C2156.08 (17)O2—N3—C12—C82.0 (3)
C7—N1—C1—C260.8 (2)O2—N3—C12—C13175.97 (16)
N2—N1—C1—C625.2 (2)C9—C8—C12—N345.2 (3)
C7—N1—C1—C6117.9 (2)C7—C8—C12—N3138.1 (2)
C6—C1—C2—C31.1 (3)C9—C8—C12—C13136.8 (2)
N1—C1—C2—C3177.57 (17)C7—C8—C12—C1339.8 (3)
C1—C2—C3—C40.8 (3)N3—C12—C13—C1869.6 (2)
C2—C3—C4—C50.5 (3)C8—C12—C13—C18108.7 (2)
C3—C4—C5—C61.6 (3)N3—C12—C13—C14109.3 (2)
C4—C5—C6—C11.3 (3)C8—C12—C13—C1472.5 (2)
C2—C1—C6—C50.1 (3)C18—C13—C14—C150.6 (3)
N1—C1—C6—C5178.60 (17)C12—C13—C14—C15178.32 (17)
N2—N1—C7—O1175.05 (17)C18—C13—C14—Cl1178.34 (13)
C1—N1—C7—O128.9 (3)C12—C13—C14—Cl10.6 (2)
N2—N1—C7—C83.21 (19)C13—C14—C15—C160.0 (3)
C1—N1—C7—C8149.40 (17)Cl1—C14—C15—C16177.69 (16)
O1—C7—C8—C9179.2 (2)C14—C15—C16—C170.9 (3)
N1—C7—C8—C91.1 (2)C15—C16—C17—C181.2 (3)
O1—C7—C8—C123.6 (3)C16—C17—C18—C130.5 (3)
N1—C7—C8—C12178.39 (16)C16—C17—C18—Cl2179.14 (17)
N1—N2—C9—C87.2 (2)C14—C13—C18—C170.4 (3)
C11—N2—C9—C8146.3 (2)C12—C13—C18—C17178.52 (18)
N1—N2—C9—C10169.2 (2)C14—C13—C18—Cl2180.00 (13)
C11—N2—C9—C1030.1 (3)C12—C13—C18—Cl21.1 (2)
 

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