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The title compound, C17H14ClN3, adopts the more stable E configuration. In the crystal structure, the pyrazole heterocycle and the adjacent benzene ring are not coplanar but inclined at 45.54 (7)°. The imine group is twisted by 5.41 (12)° away from the pyrazole ring, and by 42.59 (11)° away from the adjacent benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055390/kj2071sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055390/kj2071Isup2.hkl
Contains datablock I

CCDC reference: 672876

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Comment top

Pyrazole derivatives are attracting the increasing attention of the synthetic community for decades (Wang, 2004), owing to their wide range of biological activities in pesticide and medicine science (Liang & Bai, 2006; He, 2005). In recent years, we have been engaged in the preparation of derivatives of pyrazole compounds, and expected to find low toxicity and high activity lead compounds for the pesticide field.

Herein, we report the crystal structure of the title compound (Fig. 1), which was synthesized by the condensation reaction of aldehyde with aniline.

The title compound adopts the more stable E-configuration. In the pyrazole ring of the title molecule, bond lengths and angles are similar to those observed in closely related structures (Trilleras et al., 2005). The pyrazole ring and the adjacent benzene ring (C1–C6) are inclined at 45.54 (7)°. The imine group (N3—C11—H11) is twisted by 5.41 (12)° away from the pyrazole ring, and 42.59 (11)° away from the adjacent benzene ring (C12–C17).

Related literature top

Many derivatives of pyrazole have been prepared, and their biological activities have been studied by Wang (2004), He (2005) and Liang & Bai (2006). A closely related structure was published by Trilleras et al. (2005).

Experimental top

A solution of 5-chloro-3-methyl-1-H-pyrazole-4-carbalhedyde (5 mmol) and aniline (6 mmol) in anhydrous ethanol (20 ml) were stirred under reflux until the reaction was completed (monitored by thin-layer chromatography). After removal of ethanol under reduced pressure, the residue was recrystallized from ethanol to give the target compound as a yellow solid (yield: 86%, m.p. 395–397 K). A crystal grown from anhydrous ethanol was selected for X-ray structure analysis.

Refinement top

H atoms bonded to C were placed at calculated positions, with C—H distances of 0.97 and 0.93 Å for H atoms bonded to sp3 and sp2 C atoms, respectively. They were refined using a riding model, with Uiso(H)=1.2Ueq(C),but the methyl H atoms with Uiso(H)=1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker 2004); cell refinement: APEX2 (Bruker 2004); data reduction: SAINT (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL (Bruker 2004).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms.
(E)—N-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]benzenamine top
Crystal data top
C17H14ClN3F(000) = 616
Mr = 295.76Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.7837 (9) ÅCell parameters from 9958 reflections
b = 11.0980 (12) Åθ = 12–18°
c = 15.6749 (16) ŵ = 0.25 mm1
β = 102.648 (1)°T = 293 K
V = 1490.9 (3) Å3Block, yellow
Z = 40.40 × 0.19 × 0.18 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2751 independent reflections
Radiation source: fine-focus sealed tube2248 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.816, Tmax = 0.955k = 1313
9958 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0366P)2 + 0.4599P]
where P = (Fo2 + 2Fc2)/3
2751 reflections(Δ/σ)max = 0.002
191 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C17H14ClN3V = 1490.9 (3) Å3
Mr = 295.76Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7837 (9) ŵ = 0.25 mm1
b = 11.0980 (12) ÅT = 293 K
c = 15.6749 (16) Å0.40 × 0.19 × 0.18 mm
β = 102.648 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2751 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2248 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.955Rint = 0.021
9958 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.05Δρmax = 0.17 e Å3
2751 reflectionsΔρmin = 0.21 e Å3
191 parameters
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
Cl10.63039 (5)0.64323 (4)1.01319 (3)0.05415 (16)
N10.74453 (16)0.43848 (11)1.09347 (8)0.0404 (3)
N20.82316 (17)0.33487 (12)1.08197 (9)0.0440 (3)
N30.86228 (18)0.43674 (13)0.82194 (9)0.0515 (4)
C10.7028 (2)0.55738 (16)1.21758 (12)0.0531 (5)
H10.75390.62251.19910.064*
C20.6436 (3)0.56587 (18)1.29239 (12)0.0633 (5)
H20.65320.63771.32370.076*
C30.5710 (3)0.46867 (18)1.32053 (13)0.0627 (5)
H30.53220.47491.37100.075*
C40.5553 (2)0.36212 (17)1.27452 (12)0.0558 (5)
H40.50690.29641.29410.067*
C50.6118 (2)0.35303 (15)1.19894 (11)0.0466 (4)
H50.60070.28151.16720.056*
C60.68477 (19)0.45104 (14)1.17102 (10)0.0406 (4)
C70.73015 (19)0.50980 (14)1.02245 (10)0.0402 (4)
C80.80029 (19)0.45418 (15)0.96253 (10)0.0409 (4)
C90.85765 (19)0.34494 (15)1.00415 (10)0.0418 (4)
C100.9500 (2)0.24798 (17)0.97332 (12)0.0559 (5)
H10A0.97870.18831.01830.084*
H10B1.04250.28200.95990.084*
H10C0.88830.21110.92180.084*
C110.8068 (2)0.49883 (16)0.87614 (11)0.0454 (4)
H110.76900.57570.86000.055*
C120.8679 (2)0.48835 (16)0.73967 (11)0.0470 (4)
C130.9156 (2)0.60538 (18)0.73050 (12)0.0540 (5)
H130.94050.65560.77900.065*
C140.9263 (3)0.6478 (2)0.64888 (13)0.0655 (6)
H140.95940.72640.64310.079*
C150.8887 (3)0.5751 (2)0.57643 (13)0.0687 (6)
H150.89600.60430.52190.082*
C160.8404 (3)0.4591 (2)0.58506 (13)0.0685 (6)
H160.81340.41000.53600.082*
C170.8315 (2)0.41479 (19)0.66612 (12)0.0604 (5)
H170.80100.33540.67160.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0622 (3)0.0463 (3)0.0581 (3)0.0086 (2)0.0222 (2)0.0086 (2)
N10.0501 (8)0.0379 (7)0.0369 (7)0.0010 (6)0.0173 (6)0.0002 (6)
N20.0564 (9)0.0391 (8)0.0394 (8)0.0010 (6)0.0168 (7)0.0005 (6)
N30.0644 (10)0.0532 (9)0.0419 (8)0.0009 (7)0.0223 (7)0.0059 (7)
C10.0696 (12)0.0448 (10)0.0489 (10)0.0097 (9)0.0220 (9)0.0056 (8)
C20.0918 (16)0.0539 (12)0.0504 (11)0.0034 (11)0.0293 (11)0.0144 (9)
C30.0837 (15)0.0666 (13)0.0474 (11)0.0015 (11)0.0351 (10)0.0037 (9)
C40.0721 (13)0.0549 (11)0.0477 (10)0.0054 (9)0.0289 (9)0.0048 (9)
C50.0605 (11)0.0423 (9)0.0411 (9)0.0021 (8)0.0196 (8)0.0001 (7)
C60.0477 (10)0.0435 (9)0.0330 (8)0.0000 (7)0.0140 (7)0.0006 (7)
C70.0437 (9)0.0381 (9)0.0406 (9)0.0039 (7)0.0134 (7)0.0032 (7)
C80.0433 (9)0.0443 (9)0.0379 (8)0.0059 (7)0.0151 (7)0.0004 (7)
C90.0474 (10)0.0422 (9)0.0387 (9)0.0036 (7)0.0156 (7)0.0012 (7)
C100.0671 (12)0.0535 (11)0.0542 (11)0.0063 (9)0.0285 (9)0.0004 (9)
C110.0483 (10)0.0474 (10)0.0434 (9)0.0016 (8)0.0161 (8)0.0069 (8)
C120.0489 (10)0.0554 (11)0.0406 (9)0.0078 (8)0.0185 (8)0.0078 (8)
C130.0572 (11)0.0635 (12)0.0431 (10)0.0049 (9)0.0149 (8)0.0047 (9)
C140.0731 (14)0.0708 (14)0.0569 (12)0.0066 (11)0.0240 (10)0.0171 (10)
C150.0809 (15)0.0877 (16)0.0448 (11)0.0160 (13)0.0295 (10)0.0163 (11)
C160.0896 (16)0.0768 (15)0.0441 (11)0.0179 (12)0.0257 (10)0.0026 (10)
C170.0789 (14)0.0554 (11)0.0529 (11)0.0069 (10)0.0279 (10)0.0002 (9)
Geometric parameters (Å, º) top
Cl1—C71.7106 (17)C8—C91.416 (2)
N1—C71.349 (2)C8—C111.455 (2)
N1—N21.3734 (18)C9—C101.490 (2)
N1—C61.4324 (19)C10—H10A0.9600
N2—C91.324 (2)C10—H10B0.9600
N3—C111.271 (2)C10—H10C0.9600
N3—C121.422 (2)C11—H110.9300
C1—C61.378 (2)C12—C131.382 (3)
C1—C21.386 (2)C12—C171.392 (3)
C1—H10.9300C13—C141.386 (2)
C2—C31.374 (3)C13—H130.9300
C2—H20.9300C14—C151.373 (3)
C3—C41.376 (3)C14—H140.9300
C3—H30.9300C15—C161.371 (3)
C4—C51.384 (2)C15—H150.9300
C4—H40.9300C16—C171.381 (3)
C5—C61.382 (2)C16—H160.9300
C5—H50.9300C17—H170.9300
C7—C81.377 (2)
C7—N1—N2109.99 (13)N2—C9—C10119.23 (15)
C7—N1—C6131.12 (14)C8—C9—C10129.25 (15)
N2—N1—C6118.76 (12)C9—C10—H10A109.5
C9—N2—N1105.86 (13)C9—C10—H10B109.5
C11—N3—C12118.84 (15)H10A—C10—H10B109.5
C6—C1—C2119.03 (17)C9—C10—H10C109.5
C6—C1—H1120.5H10A—C10—H10C109.5
C2—C1—H1120.5H10B—C10—H10C109.5
C3—C2—C1120.31 (18)N3—C11—C8122.45 (16)
C3—C2—H2119.8N3—C11—H11118.8
C1—C2—H2119.8C8—C11—H11118.8
C2—C3—C4120.43 (17)C13—C12—C17119.01 (16)
C2—C3—H3119.8C13—C12—N3123.00 (16)
C4—C3—H3119.8C17—C12—N3117.90 (17)
C3—C4—C5119.84 (17)C12—C13—C14119.93 (18)
C3—C4—H4120.1C12—C13—H13120.0
C5—C4—H4120.1C14—C13—H13120.0
C6—C5—C4119.45 (16)C15—C14—C13120.7 (2)
C6—C5—H5120.3C15—C14—H14119.6
C4—C5—H5120.3C13—C14—H14119.6
C1—C6—C5120.92 (15)C16—C15—C14119.58 (18)
C1—C6—N1120.77 (15)C16—C15—H15120.2
C5—C6—N1118.29 (14)C14—C15—H15120.2
N1—C7—C8108.96 (14)C15—C16—C17120.4 (2)
N1—C7—Cl1122.11 (12)C15—C16—H16119.8
C8—C7—Cl1128.87 (13)C17—C16—H16119.8
C7—C8—C9103.69 (14)C16—C17—C12120.3 (2)
C7—C8—C11126.65 (16)C16—C17—H17119.9
C9—C8—C11129.64 (15)C12—C17—H17119.9
N2—C9—C8111.50 (14)
C7—N1—N2—C90.75 (18)Cl1—C7—C8—C110.9 (3)
C6—N1—N2—C9176.95 (14)N1—N2—C9—C80.95 (18)
C6—C1—C2—C31.3 (3)N1—N2—C9—C10177.53 (15)
C1—C2—C3—C40.4 (3)C7—C8—C9—N20.79 (19)
C2—C3—C4—C50.6 (3)C11—C8—C9—N2177.42 (16)
C3—C4—C5—C60.6 (3)C7—C8—C9—C10177.49 (18)
C2—C1—C6—C51.3 (3)C11—C8—C9—C104.3 (3)
C2—C1—C6—N1179.85 (17)C12—N3—C11—C8178.45 (16)
C4—C5—C6—C10.3 (3)C7—C8—C11—N3173.72 (17)
C4—C5—C6—N1178.91 (16)C9—C8—C11—N34.1 (3)
C7—N1—C6—C149.2 (3)C11—N3—C12—C1343.5 (3)
N2—N1—C6—C1135.51 (17)C11—N3—C12—C17140.12 (18)
C7—N1—C6—C5132.20 (18)C17—C12—C13—C140.1 (3)
N2—N1—C6—C543.1 (2)N3—C12—C13—C14176.48 (18)
N2—N1—C7—C80.27 (19)C12—C13—C14—C150.5 (3)
C6—N1—C7—C8175.84 (15)C13—C14—C15—C160.2 (3)
N2—N1—C7—Cl1177.06 (11)C14—C15—C16—C170.9 (3)
C6—N1—C7—Cl11.5 (2)C15—C16—C17—C121.6 (3)
N1—C7—C8—C90.30 (18)C13—C12—C17—C161.2 (3)
Cl1—C7—C8—C9177.38 (13)N3—C12—C17—C16177.71 (18)
N1—C7—C8—C11177.98 (15)

Experimental details

Crystal data
Chemical formulaC17H14ClN3
Mr295.76
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.7837 (9), 11.0980 (12), 15.6749 (16)
β (°) 102.648 (1)
V3)1490.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.40 × 0.19 × 0.18
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.816, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections
9958, 2751, 2248
Rint0.021
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.05
No. of reflections2751
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.21

Computer programs: APEX2 (Bruker 2004), SAINT (Bruker 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker 2004).

 

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