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In the title structure, C21H16BrClN2, the pyrazoline ring is approximately coplanar with the N-substituted phenyl ring. The dihedral angles formed by the pyrazoline ring with the 4-chloro­phenyl and 4-bromo­phenyl rings are 78.82 and 10.9°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700102X/at2198sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700102X/at2198Isup2.hkl
Contains datablock I

CCDC reference: 626446

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.044
  • wR factor = 0.124
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.548 0.620 RT(exp) = 1.133 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.01
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.03 From the CIF: _reflns_number_total 3899 Count of symmetry unique reflns 2294 Completeness (_total/calc) 169.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1605 Fraction of Friedel pairs measured 0.700 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-Bromophenyl)-5-(4-chlorophenyl)-1-phenyl-2-pyrazoline top
Crystal data top
C21H16BrClN2F(000) = 832
Mr = 411.72Dx = 1.488 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 10.682 (2) Åθ = 4–14°
b = 11.154 (2) ŵ = 2.39 mm1
c = 15.430 (3) ÅT = 293 K
V = 1838.4 (6) Å3Column, yellow
Z = 40.26 × 0.24 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 2.3°
Graphite monochromatorh = 1113
ω scansk = 1114
8675 measured reflectionsl = 1919
3899 independent reflections3 standard reflections every 100 reflections
2464 reflections with I > 2σ(I) intensity decay: none
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0682P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
3899 reflectionsΔρmax = 0.35 e Å3
226 parametersΔρmin = 0.34 e Å3
0 restraintsAbsolute structure: Flack (1983), 1605 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (1)
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
Br10.77349 (5)0.93503 (6)0.12567 (4)0.0844 (2)
Cl10.0500 (2)1.39829 (12)0.58739 (10)0.1073 (7)
N10.1876 (3)0.8977 (3)0.3064 (2)0.0456 (8)
N20.0675 (3)0.9297 (3)0.3258 (2)0.0536 (8)
C10.0258 (5)1.2975 (4)0.5033 (3)0.0648 (14)
C20.0911 (5)1.3099 (4)0.4285 (4)0.0728 (15)
H2A0.14781.37250.42180.087*
C30.0728 (4)1.2286 (4)0.3623 (3)0.0628 (12)
H3A0.11811.23580.31110.075*
C40.0127 (3)1.1365 (4)0.3717 (3)0.0481 (9)
C50.0786 (5)1.1273 (4)0.4477 (3)0.0596 (12)
H5A0.13701.06620.45450.072*
C60.0590 (5)1.2076 (4)0.5140 (3)0.0636 (13)
H6A0.10331.20050.56570.076*
C70.1530 (4)1.0837 (4)0.2438 (3)0.0587 (12)
H7A0.13361.08980.18250.070*
H7B0.18981.15850.26320.070*
C80.0358 (4)1.0523 (4)0.2969 (3)0.0524 (10)
H8A0.03781.05020.25900.063*
C90.2376 (4)0.9807 (3)0.2615 (2)0.0426 (9)
C100.0089 (4)0.8565 (4)0.3748 (3)0.0480 (9)
C110.1325 (4)0.8855 (4)0.3901 (3)0.0560 (11)
H11A0.16630.95450.36570.067*
C120.2059 (5)0.8134 (5)0.4412 (3)0.0627 (13)
H12A0.28890.83420.45130.075*
C130.1579 (5)0.7102 (5)0.4777 (3)0.0632 (13)
H13A0.20750.66190.51280.076*
C140.0370 (5)0.6806 (4)0.4614 (3)0.0609 (12)
H14A0.00470.61070.48550.073*
C150.0399 (4)0.7510 (4)0.4100 (3)0.0534 (11)
H15A0.12230.72850.39920.064*
C160.3670 (4)0.9708 (3)0.2297 (2)0.0446 (10)
C170.4454 (4)0.8796 (4)0.2578 (3)0.0563 (11)
H17A0.41570.82320.29710.068*
C180.5661 (4)0.8718 (4)0.2282 (3)0.0611 (12)
H18A0.61890.81160.24840.073*
C190.6082 (4)0.9533 (4)0.1688 (3)0.0561 (11)
C200.5332 (4)1.0433 (4)0.1386 (3)0.0553 (11)
H20A0.56261.09780.09780.066*
C210.4133 (4)1.0514 (4)0.1702 (3)0.0521 (10)
H21A0.36191.11320.15080.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0535 (3)0.0960 (4)0.1038 (4)0.0030 (3)0.0204 (3)0.0002 (4)
Cl10.1847 (19)0.0612 (8)0.0758 (9)0.0057 (10)0.0418 (11)0.0099 (7)
N10.046 (2)0.0462 (19)0.0446 (19)0.0003 (15)0.0025 (15)0.0034 (16)
N20.051 (2)0.0456 (19)0.064 (2)0.0015 (19)0.0099 (17)0.0040 (18)
C10.088 (4)0.046 (3)0.060 (3)0.002 (3)0.025 (3)0.007 (2)
C20.089 (4)0.054 (3)0.076 (4)0.025 (3)0.018 (3)0.014 (3)
C30.063 (3)0.061 (3)0.065 (3)0.014 (2)0.006 (3)0.011 (2)
C40.044 (2)0.046 (2)0.054 (2)0.0029 (18)0.010 (2)0.008 (2)
C50.061 (3)0.059 (3)0.059 (3)0.011 (2)0.003 (2)0.001 (2)
C60.083 (4)0.061 (3)0.046 (3)0.003 (3)0.002 (3)0.003 (2)
C70.066 (3)0.058 (3)0.051 (3)0.016 (2)0.015 (2)0.012 (2)
C80.054 (2)0.055 (2)0.048 (2)0.003 (2)0.0009 (19)0.007 (2)
C90.050 (2)0.041 (2)0.037 (2)0.0019 (19)0.0022 (18)0.0025 (17)
C100.051 (2)0.051 (2)0.043 (2)0.0085 (19)0.002 (2)0.006 (2)
C110.052 (3)0.057 (3)0.059 (3)0.000 (2)0.001 (2)0.004 (2)
C120.054 (3)0.074 (3)0.060 (3)0.012 (3)0.011 (2)0.009 (3)
C130.064 (3)0.072 (3)0.054 (3)0.021 (3)0.008 (2)0.001 (2)
C140.062 (3)0.058 (3)0.063 (3)0.014 (2)0.004 (2)0.009 (2)
C150.052 (3)0.051 (2)0.057 (2)0.007 (2)0.003 (2)0.003 (2)
C160.053 (2)0.045 (2)0.036 (2)0.0004 (19)0.0031 (18)0.0056 (18)
C170.060 (3)0.051 (3)0.058 (3)0.000 (2)0.002 (2)0.004 (2)
C180.057 (3)0.060 (3)0.066 (3)0.011 (2)0.001 (2)0.006 (2)
C190.045 (2)0.062 (3)0.061 (3)0.004 (2)0.004 (2)0.006 (2)
C200.061 (3)0.052 (2)0.052 (3)0.006 (2)0.013 (2)0.005 (2)
C210.058 (3)0.048 (2)0.051 (2)0.001 (2)0.007 (2)0.001 (2)
Geometric parameters (Å, º) top
Br1—C191.897 (4)C9—C161.471 (6)
Cl1—C11.736 (5)C10—C111.380 (6)
N1—C91.274 (5)C10—C151.397 (6)
N1—N21.364 (5)C11—C121.372 (6)
N2—C101.380 (5)C11—H11A0.9300
N2—C81.478 (6)C12—C131.380 (7)
C1—C21.356 (8)C12—H12A0.9300
C1—C61.362 (7)C13—C141.356 (7)
C2—C31.379 (7)C13—H13A0.9300
C2—H2A0.9300C14—C151.386 (6)
C3—C41.383 (6)C14—H14A0.9300
C3—H3A0.9300C15—H15A0.9300
C4—C51.371 (6)C16—C211.377 (6)
C4—C81.509 (6)C16—C171.387 (6)
C5—C61.375 (7)C17—C181.371 (6)
C5—H5A0.9300C17—H17A0.9300
C6—H6A0.9300C18—C191.368 (6)
C7—C91.487 (6)C18—H18A0.9300
C7—C81.536 (6)C19—C201.366 (6)
C7—H7A0.9700C20—C211.373 (6)
C7—H7B0.9700C20—H20A0.9300
C8—H8A0.9800C21—H21A0.9300
C9—N1—N2108.8 (3)C11—C10—N2121.4 (4)
N1—N2—C10121.4 (3)C11—C10—C15119.2 (4)
N1—N2—C8113.0 (3)N2—C10—C15119.4 (4)
C10—N2—C8125.2 (4)C12—C11—C10120.5 (5)
C2—C1—C6121.4 (5)C12—C11—H11A119.7
C2—C1—Cl1119.6 (4)C10—C11—H11A119.7
C6—C1—Cl1119.0 (4)C11—C12—C13120.7 (5)
C1—C2—C3119.4 (5)C11—C12—H12A119.6
C1—C2—H2A120.3C13—C12—H12A119.6
C3—C2—H2A120.3C14—C13—C12118.7 (5)
C2—C3—C4120.3 (5)C14—C13—H13A120.6
C2—C3—H3A119.9C12—C13—H13A120.6
C4—C3—H3A119.9C13—C14—C15122.2 (5)
C5—C4—C3119.0 (4)C13—C14—H14A118.9
C5—C4—C8121.6 (4)C15—C14—H14A118.9
C3—C4—C8119.3 (4)C14—C15—C10118.6 (4)
C4—C5—C6120.6 (4)C14—C15—H15A120.7
C4—C5—H5A119.7C10—C15—H15A120.7
C6—C5—H5A119.7C21—C16—C17118.0 (4)
C1—C6—C5119.3 (5)C21—C16—C9120.8 (4)
C1—C6—H6A120.3C17—C16—C9121.2 (4)
C5—C6—H6A120.3C18—C17—C16120.7 (4)
C9—C7—C8102.8 (3)C18—C17—H17A119.6
C9—C7—H7A111.2C16—C17—H17A119.6
C8—C7—H7A111.2C19—C18—C17119.3 (4)
C9—C7—H7B111.2C19—C18—H18A120.3
C8—C7—H7B111.2C17—C18—H18A120.3
H7A—C7—H7B109.1C20—C19—C18121.6 (4)
N2—C8—C4112.5 (3)C20—C19—Br1120.4 (3)
N2—C8—C7100.7 (3)C18—C19—Br1118.0 (4)
C4—C8—C7113.5 (4)C19—C20—C21118.3 (4)
N2—C8—H8A109.9C19—C20—H20A120.8
C4—C8—H8A109.9C21—C20—H20A120.8
C7—C8—H8A109.9C20—C21—C16121.9 (4)
N1—C9—C16121.4 (4)C20—C21—H21A119.0
N1—C9—C7114.0 (4)C16—C21—H21A119.0
C16—C9—C7124.6 (3)
 

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