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The title compound, C18H15Cl2N3O, is a Schiff base. It crystallizes with two mol­ecules in the asymmetric unit. The dihydro-1H-pyrazole rings show a π–π stacking inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042887/bt2200sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042887/bt2200Isup2.hkl
Contains datablock I

CCDC reference: 627353

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.094
  • wR factor = 0.329
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 5569 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5912 Completeness (_total/calc) 94.20% RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.329 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT084_ALERT_2_C High R2 Value .................................. 0.33 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 5 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 (Bruker,1998); 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, 1998); software used to prepare material for publication: SHELXTL.

4-(2,6-Dichlorobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top
Crystal data top
C18H15Cl2N3OF(000) = 1488
Mr = 360.23Dx = 1.421 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.591 (5) ÅCell parameters from 5299 reflections
b = 25.808 (18) Åθ = 2.4–25.1°
c = 17.216 (12) ŵ = 0.40 mm1
β = 92.823 (8)°T = 273 K
V = 3369 (4) Å3Block, yellow
Z = 80.37 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5569 independent reflections
Radiation source: fine-focus sealed tube3386 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.868, Tmax = 0.925k = 3030
19762 measured reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.094H-atom parameters constrained
wR(F2) = 0.329 w = 1/[σ2(Fo2) + (0.1683P)2 + 4.5478P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
5569 reflectionsΔρmax = 0.48 e Å3
438 parametersΔρmin = 1.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (3)
Special details top

Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 9.98 (s, 1H), 7.52–7.17 (m, 8H), 3.21 (s, 3H), 2.49 (s, 3H); IR (KBr, ν, cm-1): 3437, 3044, 2940, 1651, 1580, 1491, 1415, 1307, 1187, 1132, 946, 775, 694.

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
C10.6930 (11)0.6266 (3)0.1237 (5)0.083 (2)
H10.71290.66160.11510.100*
C20.6268 (11)0.6109 (3)0.1929 (4)0.077 (2)
H20.60470.63510.23130.092*
C30.5939 (10)0.5595 (3)0.2047 (4)0.0670 (17)
C40.6275 (9)0.5212 (2)0.1492 (3)0.0594 (15)
C50.6988 (10)0.5393 (3)0.0806 (4)0.0678 (18)
C60.7298 (11)0.5912 (3)0.0671 (4)0.077 (2)
H60.77480.60200.02050.093*
C70.5818 (9)0.4659 (2)0.1558 (4)0.0613 (16)
H70.54310.44820.11110.074*
C80.5416 (9)0.3894 (2)0.2220 (3)0.0590 (16)
C90.5574 (9)0.3595 (2)0.2884 (3)0.0561 (15)
C100.6120 (11)0.3763 (3)0.3689 (3)0.0708 (19)
H10A0.51350.37350.40150.106*
H10B0.65130.41170.36800.106*
H10C0.70630.35460.38900.106*
C110.4462 (10)0.2730 (3)0.3267 (4)0.0704 (18)
H11A0.51650.27440.37460.106*
H11B0.45210.23880.30510.106*
H11C0.32600.28120.33650.106*
C120.4485 (9)0.2605 (2)0.1528 (3)0.0581 (15)
C130.3126 (10)0.2498 (3)0.0986 (4)0.0700 (18)
H130.22190.27350.08880.084*
C140.3151 (13)0.2032 (3)0.0594 (4)0.083 (2)
H140.22580.19590.02210.100*
C150.4451 (13)0.1675 (3)0.0739 (4)0.086 (3)
H150.44190.13600.04780.103*
C160.5815 (13)0.1784 (3)0.1275 (4)0.083 (2)
H160.67130.15440.13710.099*
C170.5841 (10)0.2251 (2)0.1669 (4)0.0672 (18)
H170.67620.23270.20260.081*
C180.4735 (10)0.3566 (2)0.1601 (3)0.0618 (16)
C1'0.7931 (11)0.1101 (3)0.3729 (4)0.078 (2)
H1'0.75450.07610.37830.093*
C2'0.8741 (10)0.1248 (3)0.3069 (4)0.0716 (19)
H2'0.89000.10070.26760.086*
C3'0.9326 (10)0.1752 (2)0.2984 (4)0.0636 (17)
C4'0.9103 (9)0.2127 (2)0.3558 (3)0.0591 (15)
C5'0.8273 (10)0.1961 (3)0.4224 (4)0.0674 (18)
C6'0.7687 (11)0.1456 (3)0.4313 (4)0.078 (2)
H6'0.71360.13580.47610.094*
C7'0.9718 (9)0.2667 (2)0.3509 (3)0.0595 (15)
H7'1.01850.28280.39570.071*
C8'1.0200 (9)0.3438 (2)0.2855 (3)0.0557 (15)
C9'1.0025 (9)0.3743 (2)0.2201 (3)0.0570 (15)
C10'0.9456 (10)0.3584 (3)0.1398 (3)0.0690 (18)
H10D0.85160.38060.12060.104*
H10E0.90500.32320.14020.104*
H10F1.04330.36130.10680.104*
C11'1.1085 (10)0.4618 (3)0.1831 (4)0.073 (2)
H11D1.22560.45290.16910.110*
H11E1.10980.49550.20690.110*
H11F1.03110.46230.13730.110*
C12'1.1033 (9)0.4725 (2)0.3582 (3)0.0608 (16)
C13'0.9642 (11)0.5060 (3)0.3444 (4)0.0724 (19)
H13'0.87490.49840.30720.087*
C14'0.9603 (13)0.5513 (3)0.3872 (5)0.088 (2)
H14'0.86900.57480.37750.106*
C15'1.0883 (14)0.5623 (3)0.4435 (5)0.090 (3)
H15'1.08300.59270.47230.108*
C16'1.2242 (13)0.5281 (3)0.4573 (4)0.090 (2)
H16'1.31060.53530.49600.108*
C17'1.2347 (11)0.4829 (3)0.4144 (4)0.0739 (19)
H17'1.32820.46000.42320.089*
C18'1.0880 (9)0.3758 (2)0.3484 (3)0.0589 (16)
Cl10.4916 (3)0.54329 (7)0.28996 (10)0.0794 (6)
Cl20.7512 (3)0.49492 (8)0.00907 (10)0.0843 (7)
Cl1'0.7895 (3)0.24020 (8)0.49602 (10)0.0891 (7)
Cl2'1.0449 (3)0.18909 (7)0.21537 (10)0.0752 (6)
N10.5930 (8)0.44116 (19)0.2199 (3)0.0593 (13)
N20.5130 (8)0.31018 (18)0.2721 (3)0.0592 (14)
N30.4479 (8)0.30849 (18)0.1943 (3)0.0613 (14)
N1'0.9633 (8)0.29229 (19)0.2873 (3)0.0600 (13)
N2'1.0462 (8)0.42362 (18)0.2378 (3)0.0583 (13)
N3'1.1135 (8)0.42482 (18)0.3152 (3)0.0591 (13)
O10.4440 (8)0.36525 (17)0.0898 (2)0.0798 (15)
O1'1.1236 (7)0.36631 (16)0.4178 (2)0.0752 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.103 (6)0.054 (4)0.092 (6)0.014 (4)0.007 (5)0.009 (4)
C20.100 (6)0.051 (4)0.079 (5)0.004 (4)0.004 (4)0.008 (3)
C30.095 (5)0.055 (4)0.051 (4)0.001 (3)0.001 (3)0.004 (3)
C40.083 (4)0.050 (3)0.044 (3)0.004 (3)0.002 (3)0.003 (3)
C50.090 (5)0.061 (4)0.052 (4)0.003 (3)0.007 (3)0.005 (3)
C60.100 (5)0.073 (5)0.060 (4)0.010 (4)0.001 (4)0.019 (4)
C70.083 (4)0.052 (4)0.048 (3)0.002 (3)0.001 (3)0.002 (3)
C80.091 (4)0.045 (3)0.042 (3)0.003 (3)0.001 (3)0.000 (3)
C90.078 (4)0.048 (3)0.042 (3)0.007 (3)0.007 (3)0.002 (3)
C100.105 (5)0.064 (4)0.043 (3)0.001 (4)0.002 (3)0.006 (3)
C110.094 (5)0.069 (4)0.049 (4)0.002 (4)0.004 (3)0.011 (3)
C120.088 (4)0.044 (3)0.042 (3)0.002 (3)0.004 (3)0.001 (3)
C130.088 (5)0.070 (4)0.051 (4)0.001 (4)0.007 (3)0.003 (3)
C140.120 (7)0.081 (5)0.048 (4)0.020 (5)0.001 (4)0.014 (4)
C150.150 (8)0.054 (4)0.057 (4)0.007 (5)0.024 (5)0.010 (3)
C160.135 (7)0.057 (4)0.056 (4)0.012 (4)0.012 (5)0.001 (3)
C170.101 (5)0.052 (4)0.048 (3)0.005 (3)0.000 (3)0.002 (3)
C180.096 (5)0.047 (3)0.042 (3)0.008 (3)0.001 (3)0.003 (3)
C1'0.099 (6)0.061 (4)0.072 (5)0.017 (4)0.009 (4)0.015 (4)
C2'0.092 (5)0.051 (4)0.071 (4)0.003 (3)0.002 (4)0.000 (3)
C3'0.087 (4)0.052 (4)0.052 (4)0.003 (3)0.003 (3)0.005 (3)
C4'0.081 (4)0.051 (3)0.046 (3)0.003 (3)0.001 (3)0.005 (3)
C5'0.090 (5)0.062 (4)0.048 (4)0.006 (4)0.007 (3)0.010 (3)
C6'0.096 (5)0.079 (5)0.059 (4)0.009 (4)0.005 (4)0.025 (4)
C7'0.079 (4)0.055 (4)0.045 (3)0.003 (3)0.005 (3)0.001 (3)
C8'0.082 (4)0.044 (3)0.041 (3)0.000 (3)0.004 (3)0.002 (3)
C9'0.084 (4)0.049 (3)0.039 (3)0.004 (3)0.008 (3)0.000 (3)
C10'0.102 (5)0.062 (4)0.043 (3)0.000 (4)0.001 (3)0.001 (3)
C11'0.109 (6)0.064 (4)0.047 (3)0.010 (4)0.007 (4)0.011 (3)
C12'0.092 (5)0.046 (3)0.045 (3)0.000 (3)0.013 (3)0.002 (3)
C13'0.101 (5)0.053 (4)0.063 (4)0.009 (4)0.003 (4)0.000 (3)
C14'0.123 (7)0.058 (4)0.084 (5)0.011 (4)0.020 (5)0.004 (4)
C15'0.131 (7)0.057 (4)0.085 (6)0.009 (5)0.034 (5)0.018 (4)
C16'0.123 (7)0.085 (6)0.063 (5)0.020 (5)0.001 (5)0.020 (4)
C17'0.101 (5)0.066 (4)0.054 (4)0.006 (4)0.002 (4)0.007 (3)
C18'0.088 (4)0.047 (3)0.042 (3)0.006 (3)0.004 (3)0.005 (3)
Cl10.1132 (15)0.0627 (11)0.0638 (11)0.0023 (10)0.0198 (10)0.0072 (8)
Cl20.1141 (17)0.0882 (14)0.0517 (10)0.0005 (11)0.0157 (10)0.0009 (9)
Cl1'0.1342 (18)0.0842 (13)0.0503 (10)0.0090 (12)0.0186 (11)0.0044 (8)
Cl2'0.1086 (14)0.0595 (10)0.0589 (10)0.0028 (9)0.0190 (9)0.0015 (8)
N10.085 (4)0.044 (3)0.048 (3)0.000 (3)0.003 (3)0.001 (2)
N20.097 (4)0.043 (3)0.038 (3)0.001 (3)0.001 (3)0.001 (2)
N30.098 (4)0.047 (3)0.039 (3)0.002 (3)0.004 (3)0.003 (2)
N1'0.090 (4)0.045 (3)0.045 (3)0.005 (3)0.001 (3)0.002 (2)
N2'0.093 (4)0.045 (3)0.037 (2)0.004 (3)0.005 (2)0.004 (2)
N3'0.090 (4)0.045 (3)0.041 (3)0.000 (3)0.006 (3)0.002 (2)
O10.132 (4)0.058 (3)0.047 (3)0.001 (3)0.020 (3)0.006 (2)
O1'0.124 (4)0.055 (3)0.045 (2)0.003 (3)0.014 (2)0.005 (2)
Geometric parameters (Å, º) top
C1—C61.374 (11)C1'—C6'1.379 (11)
C1—C21.378 (10)C1'—H1'0.9300
C1—H10.9300C2'—C3'1.384 (9)
C2—C31.367 (9)C2'—H2'0.9300
C2—H20.9300C3'—C4'1.399 (9)
C3—C41.407 (9)C3'—Cl2'1.738 (7)
C3—Cl11.744 (7)C4'—C5'1.403 (9)
C4—C51.404 (9)C4'—C7'1.474 (9)
C4—C71.475 (9)C5'—C6'1.388 (10)
C5—C61.382 (10)C5'—Cl1'1.738 (7)
C5—Cl21.743 (7)C6'—H6'0.9300
C6—H60.9300C7'—N1'1.277 (7)
C7—N11.274 (7)C7'—H7'0.9300
C7—H70.9300C8'—C9'1.375 (8)
C8—C91.378 (8)C8'—N1'1.398 (8)
C8—N11.393 (8)C8'—C18'1.437 (8)
C8—C181.436 (8)C9'—N2'1.347 (8)
C9—N21.342 (8)C9'—C10'1.486 (8)
C9—C101.492 (8)C10'—H10D0.9600
C10—H10A0.9600C10'—H10E0.9600
C10—H10B0.9600C10'—H10F0.9600
C10—H10C0.9600C11'—N2'1.459 (8)
C11—N21.453 (8)C11'—H11D0.9600
C11—H11A0.9600C11'—H11E0.9600
C11—H11B0.9600C11'—H11F0.9600
C11—H11C0.9600C12'—C13'1.377 (9)
C12—C131.385 (9)C12'—C17'1.381 (9)
C12—C171.388 (9)C12'—N3'1.439 (7)
C12—N31.430 (7)C13'—C14'1.384 (10)
C13—C141.379 (10)C13'—H13'0.9300
C13—H130.9300C14'—C15'1.367 (12)
C14—C151.363 (11)C14'—H14'0.9300
C14—H140.9300C15'—C16'1.370 (12)
C15—C161.381 (12)C15'—H15'0.9300
C15—H150.9300C16'—C17'1.386 (10)
C16—C171.381 (9)C16'—H16'0.9300
C16—H160.9300C17'—H17'0.9300
C17—H170.9300C18'—O1'1.236 (7)
C18—O11.240 (7)C18'—N3'1.406 (7)
C18—N31.392 (8)N2—N31.406 (6)
C1'—C2'1.372 (10)N2'—N3'1.404 (7)
C6—C1—C2121.0 (7)C2'—C3'—Cl2'117.0 (5)
C6—C1—H1119.5C4'—C3'—Cl2'121.2 (5)
C2—C1—H1119.5C3'—C4'—C5'116.0 (6)
C3—C2—C1119.4 (7)C3'—C4'—C7'124.4 (6)
C3—C2—H2120.3C5'—C4'—C7'119.5 (6)
C1—C2—H2120.3C6'—C5'—C4'122.5 (6)
C2—C3—C4122.7 (6)C6'—C5'—Cl1'118.0 (6)
C2—C3—Cl1116.7 (5)C4'—C5'—Cl1'119.5 (5)
C4—C3—Cl1120.4 (5)C1'—C6'—C5'119.2 (7)
C5—C4—C3115.3 (6)C1'—C6'—H6'120.4
C5—C4—C7119.3 (6)C5'—C6'—H6'120.4
C3—C4—C7125.2 (6)N1'—C7'—C4'122.3 (6)
C6—C5—C4122.8 (6)N1'—C7'—H7'118.9
C6—C5—Cl2118.1 (5)C4'—C7'—H7'118.9
C4—C5—Cl2119.1 (5)C9'—C8'—N1'123.0 (5)
C1—C6—C5118.8 (7)C9'—C8'—C18'107.7 (5)
C1—C6—H6120.6N1'—C8'—C18'129.0 (5)
C5—C6—H6120.6N2'—C9'—C8'110.1 (5)
N1—C7—C4123.0 (6)N2'—C9'—C10'121.9 (5)
N1—C7—H7118.5C8'—C9'—C10'128.1 (6)
C4—C7—H7118.5C9'—C10'—H10D109.5
C9—C8—N1123.0 (5)C9'—C10'—H10E109.5
C9—C8—C18107.4 (5)H10D—C10'—H10E109.5
N1—C8—C18129.5 (5)C9'—C10'—H10F109.5
N2—C9—C8110.3 (5)H10D—C10'—H10F109.5
N2—C9—C10121.7 (5)H10E—C10'—H10F109.5
C8—C9—C10128.0 (6)N2'—C11'—H11D109.5
C9—C10—H10A109.5N2'—C11'—H11E109.5
C9—C10—H10B109.5H11D—C11'—H11E109.5
H10A—C10—H10B109.5N2'—C11'—H11F109.5
C9—C10—H10C109.5H11D—C11'—H11F109.5
H10A—C10—H10C109.5H11E—C11'—H11F109.5
H10B—C10—H10C109.5C13'—C12'—C17'121.3 (6)
N2—C11—H11A109.5C13'—C12'—N3'120.6 (6)
N2—C11—H11B109.5C17'—C12'—N3'118.1 (6)
H11A—C11—H11B109.5C12'—C13'—C14'118.4 (8)
N2—C11—H11C109.5C12'—C13'—H13'120.8
H11A—C11—H11C109.5C14'—C13'—H13'120.8
H11B—C11—H11C109.5C15'—C14'—C13'121.3 (8)
C13—C12—C17120.5 (6)C15'—C14'—H14'119.4
C13—C12—N3119.2 (6)C13'—C14'—H14'119.4
C17—C12—N3120.3 (6)C14'—C15'—C16'119.5 (7)
C14—C13—C12118.4 (7)C14'—C15'—H15'120.2
C14—C13—H13120.8C16'—C15'—H15'120.2
C12—C13—H13120.8C15'—C16'—C17'120.8 (8)
C15—C14—C13121.7 (8)C15'—C16'—H16'119.6
C15—C14—H14119.1C17'—C16'—H16'119.6
C13—C14—H14119.1C12'—C17'—C16'118.6 (8)
C14—C15—C16119.8 (7)C12'—C17'—H17'120.7
C14—C15—H15120.1C16'—C17'—H17'120.7
C16—C15—H15120.1O1'—C18'—N3'122.9 (6)
C17—C16—C15119.8 (8)O1'—C18'—C8'131.9 (6)
C17—C16—H16120.1N3'—C18'—C8'105.2 (5)
C15—C16—H16120.1C7—N1—C8119.7 (5)
C16—C17—C12119.7 (7)C9—N2—N3107.5 (4)
C16—C17—H17120.1C9—N2—C11125.7 (5)
C12—C17—H17120.1N3—N2—C11118.6 (5)
O1—C18—N3123.3 (6)C18—N3—N2109.0 (5)
O1—C18—C8131.3 (6)C18—N3—C12124.0 (5)
N3—C18—C8105.3 (5)N2—N3—C12119.5 (5)
C2'—C1'—C6'120.1 (7)C7'—N1'—C8'120.4 (5)
C2'—C1'—H1'120.0C9'—N2'—N3'108.0 (4)
C6'—C1'—H1'120.0C9'—N2'—C11'125.3 (5)
C1'—C2'—C3'120.5 (7)N3'—N2'—C11'118.9 (5)
C1'—C2'—H2'119.8N2'—N3'—C18'108.4 (5)
C3'—C2'—H2'119.8N2'—N3'—C12'118.7 (5)
C2'—C3'—C4'121.7 (6)C18'—N3'—C12'123.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.932.293.002 (8)133
C7—H7···O10.932.323.021 (8)132
 

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