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The title compound, C21H17FN2, crystallizes with two independent mol­ecules in the asymmetric unit. The pyrazoline and 4-fluoro­phenyl rings are planar. The phenyl ring at the 5-position and the pyrazoline heterocycle are almost perpendicular.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035653/bh2043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035653/bh2043Isup2.hkl
Contains datablock I

CCDC reference: 615788

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.156
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C40
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.17 From the CIF: _reflns_number_total 7160 From the CIF: _diffrn_reflns_limit_ max hkl 13. 13. 16. From the CIF: _diffrn_reflns_limit_ min hkl 0. -13. -16. TEST1: Expected hkl limits for theta max Calculated maximum hkl 14. 15. 17. Calculated minimum hkl -14. -15. -17. 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 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 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 1 ALERT type 3 Indicator that the structure quality may be low 0 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-Fluorophenyl)-1,5-diphenyl-2-pyrazoline top
Crystal data top
C21H17FN2Z = 4
Mr = 316.37F(000) = 664
Triclinic, P1Dx = 1.252 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.491 (2) ÅCell parameters from 25 reflections
b = 11.728 (2) Åθ = 4–14°
c = 13.601 (3) ŵ = 0.08 mm1
α = 89.44 (3)°T = 293 K
β = 71.07 (3)°Block, colourless
γ = 76.07 (3)°0.23 × 0.22 × 0.19 mm
V = 1678.2 (6) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 27.2°, θmin = 1.6°
Graphite monochromatorh = 013
ω scansk = 1313
7526 measured reflectionsl = 1616
7160 independent reflections3 standard reflections every 100 reflections
3538 reflections with I > 2σ(I) intensity decay: <1%
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0765P)2 + 0.0731P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7160 reflectionsΔρmax = 0.18 e Å3
434 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.08741 (14)0.82353 (14)0.43046 (13)0.1086 (5)
N10.64631 (16)0.30448 (15)0.15456 (13)0.0624 (5)
N20.53209 (15)0.38750 (14)0.17898 (13)0.0570 (4)
C10.6245 (2)0.24634 (18)0.00762 (16)0.0632 (6)
H1A0.54400.29750.01090.076*
C20.6727 (2)0.1776 (2)0.10045 (19)0.0837 (7)
H2B0.62350.18280.14360.100*
C30.7909 (3)0.1021 (3)0.1304 (2)0.0984 (9)
H3A0.82190.05540.19280.118*
C40.8628 (2)0.0965 (2)0.0668 (2)0.0896 (8)
H4A0.94400.04640.08710.108*
C50.8169 (2)0.1641 (2)0.02737 (18)0.0708 (6)
H5A0.86710.15890.06970.085*
C60.6958 (2)0.23943 (17)0.05826 (16)0.0570 (5)
C70.7188 (2)0.31911 (18)0.22277 (16)0.0609 (6)
H7A0.79640.34150.18190.073*
C80.75378 (19)0.20678 (17)0.27632 (15)0.0559 (5)
C90.8733 (2)0.1669 (2)0.28213 (19)0.0803 (7)
H9A0.93450.20830.25350.096*
C100.9035 (3)0.0634 (3)0.3315 (2)0.1008 (10)
H10A0.98510.03650.33470.121*
C110.8147 (3)0.0016 (2)0.3749 (2)0.0949 (9)
H11A0.83600.06710.40670.114*
C120.6962 (3)0.0412 (2)0.37099 (19)0.0842 (7)
H12A0.63500.00050.40140.101*
C130.6651 (2)0.14355 (19)0.32141 (17)0.0662 (6)
H13A0.58310.16960.31870.079*
C140.6277 (2)0.42368 (18)0.29869 (18)0.0679 (6)
H14A0.60220.40090.36980.081*
H14B0.66640.48910.29560.081*
C150.51749 (19)0.45446 (16)0.25977 (15)0.0532 (5)
C160.40352 (19)0.54965 (16)0.30510 (15)0.0532 (5)
C170.3937 (2)0.62659 (19)0.38623 (18)0.0693 (6)
H17A0.46070.61590.41230.083*
C180.2875 (2)0.7183 (2)0.42920 (19)0.0771 (7)
H18A0.28220.76910.48350.093*
C190.1923 (2)0.7319 (2)0.39032 (18)0.0723 (6)
C200.1959 (2)0.6575 (2)0.3114 (2)0.0867 (8)
H20A0.12750.66840.28700.104*
C210.3025 (2)0.5667 (2)0.26910 (18)0.0763 (7)
H21A0.30620.51610.21530.092*
F20.09298 (14)1.31327 (13)0.31110 (14)0.1144 (6)
N30.65692 (16)0.78987 (15)0.26011 (13)0.0614 (5)
N40.54059 (15)0.86991 (14)0.30000 (13)0.0549 (4)
C220.6427 (2)0.73102 (17)0.43473 (16)0.0601 (5)
H22A0.56220.78190.46170.072*
C230.6951 (2)0.6627 (2)0.50003 (19)0.0757 (7)
H23A0.64950.66840.57090.091*
C240.8135 (3)0.5860 (2)0.4622 (2)0.0868 (8)
H24A0.84770.53890.50650.104*
C250.8800 (2)0.5805 (2)0.3582 (2)0.0821 (7)
H25A0.96050.52950.33190.098*
C260.8300 (2)0.64944 (18)0.29096 (19)0.0683 (6)
H26A0.87750.64520.22060.082*
C270.70956 (19)0.72450 (16)0.32852 (16)0.0541 (5)
C280.72907 (19)0.81449 (17)0.15408 (16)0.0589 (5)
H28A0.80480.83800.15560.071*
C290.76881 (18)0.70874 (17)0.07598 (15)0.0529 (5)
C300.8857 (2)0.6824 (2)0.00085 (17)0.0684 (6)
H30A0.94140.72950.00450.082*
C310.9220 (2)0.5872 (2)0.07292 (19)0.0815 (7)
H31A1.00170.57080.12420.098*
C320.8416 (3)0.5167 (2)0.06937 (18)0.0748 (7)
H32A0.86670.45250.11770.090*
C330.7246 (2)0.54148 (19)0.00544 (18)0.0723 (6)
H33A0.66920.49450.00790.087*
C340.6878 (2)0.63759 (18)0.07863 (16)0.0626 (6)
H34A0.60800.65380.12960.075*
C350.6354 (2)0.92108 (18)0.13170 (17)0.0677 (6)
H35A0.67130.98880.11810.081*
H35B0.61140.90260.07280.081*
C360.52495 (18)0.94248 (16)0.23027 (15)0.0529 (5)
C370.40919 (19)1.03749 (16)0.25094 (16)0.0527 (5)
C380.3991 (2)1.12207 (19)0.17893 (19)0.0710 (6)
H38A0.46571.11590.11650.085*
C390.2926 (2)1.2142 (2)0.1988 (2)0.0827 (7)
H39A0.28641.26990.15040.099*
C400.1977 (2)1.2218 (2)0.2898 (2)0.0766 (7)
C410.2020 (2)1.1395 (2)0.3624 (2)0.0842 (8)
H41A0.13401.14590.42380.101*
C420.3087 (2)1.0479 (2)0.34238 (17)0.0712 (6)
H42A0.31320.99230.39110.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0860 (10)0.0963 (11)0.1091 (12)0.0221 (9)0.0181 (9)0.0227 (9)
N10.0620 (11)0.0566 (10)0.0633 (11)0.0003 (9)0.0238 (9)0.0039 (9)
N20.0576 (11)0.0520 (10)0.0562 (10)0.0091 (8)0.0152 (8)0.0015 (8)
C10.0645 (13)0.0592 (13)0.0611 (13)0.0146 (11)0.0149 (11)0.0013 (10)
C20.0785 (17)0.0968 (19)0.0693 (16)0.0193 (15)0.0174 (13)0.0172 (14)
C30.090 (2)0.107 (2)0.0771 (18)0.0072 (17)0.0116 (16)0.0343 (16)
C40.0686 (16)0.0901 (19)0.0846 (18)0.0003 (14)0.0051 (15)0.0170 (15)
C50.0658 (15)0.0662 (14)0.0698 (15)0.0091 (12)0.0139 (12)0.0021 (12)
C60.0632 (13)0.0459 (11)0.0561 (12)0.0149 (10)0.0113 (11)0.0019 (9)
C70.0581 (13)0.0567 (13)0.0668 (13)0.0129 (10)0.0203 (11)0.0021 (10)
C80.0537 (12)0.0532 (12)0.0559 (12)0.0037 (10)0.0181 (10)0.0067 (10)
C90.0562 (14)0.0999 (19)0.0755 (16)0.0018 (13)0.0221 (12)0.0026 (14)
C100.082 (2)0.117 (2)0.0733 (18)0.0367 (18)0.0293 (16)0.0077 (17)
C110.133 (3)0.0651 (17)0.0682 (17)0.0183 (18)0.0400 (18)0.0067 (13)
C120.127 (2)0.0622 (15)0.0764 (17)0.0324 (16)0.0448 (16)0.0080 (13)
C130.0732 (15)0.0600 (13)0.0720 (14)0.0171 (12)0.0325 (12)0.0009 (11)
C140.0767 (15)0.0497 (12)0.0789 (15)0.0087 (11)0.0330 (13)0.0063 (11)
C150.0593 (13)0.0465 (11)0.0527 (12)0.0152 (10)0.0157 (10)0.0035 (9)
C160.0578 (12)0.0462 (11)0.0528 (12)0.0144 (10)0.0137 (10)0.0027 (9)
C170.0713 (15)0.0589 (13)0.0766 (15)0.0088 (12)0.0280 (12)0.0103 (12)
C180.0808 (17)0.0621 (14)0.0797 (16)0.0024 (13)0.0254 (14)0.0194 (12)
C190.0631 (15)0.0640 (15)0.0690 (15)0.0020 (12)0.0070 (12)0.0056 (12)
C200.0687 (16)0.0982 (19)0.0845 (17)0.0023 (15)0.0299 (14)0.0156 (15)
C210.0715 (16)0.0773 (16)0.0731 (15)0.0017 (13)0.0262 (13)0.0208 (12)
F20.0942 (11)0.0851 (10)0.1362 (14)0.0306 (9)0.0395 (10)0.0049 (9)
N30.0587 (10)0.0543 (10)0.0552 (10)0.0061 (8)0.0123 (8)0.0019 (8)
N40.0548 (10)0.0481 (9)0.0566 (10)0.0044 (8)0.0174 (8)0.0021 (8)
C220.0616 (13)0.0513 (12)0.0654 (14)0.0104 (10)0.0212 (11)0.0058 (10)
C230.0821 (17)0.0755 (16)0.0731 (15)0.0203 (14)0.0306 (13)0.0239 (13)
C240.0872 (19)0.0792 (17)0.098 (2)0.0091 (15)0.0447 (17)0.0315 (15)
C250.0682 (15)0.0670 (15)0.104 (2)0.0027 (12)0.0344 (15)0.0104 (14)
C260.0635 (14)0.0565 (13)0.0747 (15)0.0005 (11)0.0202 (12)0.0006 (11)
C270.0580 (12)0.0397 (10)0.0630 (13)0.0072 (9)0.0216 (10)0.0033 (9)
C280.0570 (12)0.0525 (12)0.0590 (13)0.0080 (10)0.0123 (10)0.0014 (10)
C290.0501 (12)0.0493 (11)0.0529 (11)0.0045 (9)0.0147 (9)0.0068 (9)
C300.0562 (13)0.0717 (15)0.0668 (14)0.0117 (11)0.0094 (11)0.0053 (12)
C310.0655 (15)0.0899 (18)0.0701 (16)0.0015 (14)0.0118 (12)0.0131 (14)
C320.0904 (18)0.0582 (14)0.0666 (15)0.0071 (13)0.0321 (14)0.0061 (11)
C330.0955 (19)0.0577 (14)0.0742 (16)0.0244 (13)0.0386 (15)0.0117 (12)
C340.0631 (13)0.0621 (13)0.0576 (13)0.0151 (11)0.0138 (10)0.0075 (11)
C350.0742 (15)0.0489 (12)0.0660 (14)0.0045 (11)0.0128 (12)0.0069 (10)
C360.0582 (12)0.0436 (11)0.0568 (12)0.0102 (9)0.0208 (10)0.0031 (9)
C370.0571 (12)0.0429 (11)0.0596 (12)0.0095 (9)0.0237 (10)0.0034 (9)
C380.0680 (14)0.0595 (14)0.0793 (15)0.0096 (12)0.0211 (12)0.0216 (12)
C390.0844 (18)0.0587 (15)0.102 (2)0.0045 (13)0.0373 (16)0.0249 (14)
C400.0695 (16)0.0560 (14)0.0954 (19)0.0102 (12)0.0344 (15)0.0022 (13)
C410.0666 (15)0.0907 (18)0.0720 (16)0.0111 (14)0.0142 (12)0.0032 (14)
C420.0674 (15)0.0681 (15)0.0643 (14)0.0008 (12)0.0165 (12)0.0136 (11)
Geometric parameters (Å, º) top
F1—C191.366 (2)F2—C401.357 (2)
N1—N21.374 (2)N3—N41.378 (2)
N1—C61.396 (3)N3—C271.396 (2)
N1—C71.469 (3)N3—C281.477 (3)
N2—C151.298 (2)N4—C361.295 (2)
C1—C21.379 (3)C22—C231.376 (3)
C1—C61.386 (3)C22—C271.392 (3)
C1—H1A0.9300C22—H22A0.9300
C2—C31.365 (3)C23—C241.375 (3)
C2—H2B0.9300C23—H23A0.9300
C3—C41.368 (4)C24—C251.366 (4)
C3—H3A0.9300C24—H24A0.9300
C4—C51.389 (3)C25—C261.386 (3)
C4—H4A0.9300C25—H25A0.9300
C5—C61.389 (3)C26—C271.384 (3)
C5—H5A0.9300C26—H26A0.9300
C7—C81.531 (3)C28—C291.521 (3)
C7—C141.540 (3)C28—C351.540 (3)
C7—H7A0.9800C28—H28A0.9800
C8—C91.368 (3)C29—C301.374 (3)
C8—C131.384 (3)C29—C341.384 (3)
C9—C101.407 (4)C30—C311.384 (3)
C9—H9A0.9300C30—H30A0.9300
C10—C111.367 (4)C31—C321.370 (3)
C10—H10A0.9300C31—H31A0.9300
C11—C121.347 (4)C32—C331.363 (3)
C11—H11A0.9300C32—H32A0.9300
C12—C131.399 (3)C33—C341.400 (3)
C12—H12A0.9300C33—H33A0.9300
C13—H13A0.9300C34—H34A0.9300
C14—C151.491 (3)C35—C361.490 (3)
C14—H14A0.9700C35—H35A0.9700
C14—H14B0.9700C35—H35B0.9700
C15—C161.459 (3)C36—C371.463 (3)
C16—C211.372 (3)C37—C421.378 (3)
C16—C171.391 (3)C37—C381.399 (3)
C17—C181.381 (3)C38—C391.375 (3)
C17—H17A0.9300C38—H38A0.9300
C18—C191.338 (3)C39—C401.345 (3)
C18—H18A0.9300C39—H39A0.9300
C19—C201.373 (3)C40—C411.378 (3)
C20—C211.376 (3)C41—C421.373 (3)
C20—H20A0.9300C41—H41A0.9300
C21—H21A0.9300C42—H42A0.9300
N2—N1—C6119.54 (17)N4—N3—C27119.02 (16)
N2—N1—C7112.50 (16)N4—N3—C28112.10 (15)
C6—N1—C7125.62 (17)C27—N3—C28125.33 (17)
C15—N2—N1109.29 (17)C36—N4—N3109.16 (16)
C2—C1—C6120.3 (2)C23—C22—C27120.4 (2)
C2—C1—H1A119.9C23—C22—H22A119.8
C6—C1—H1A119.9C27—C22—H22A119.8
C3—C2—C1121.5 (3)C24—C23—C22121.1 (2)
C3—C2—H2B119.3C24—C23—H23A119.4
C1—C2—H2B119.3C22—C23—H23A119.4
C2—C3—C4118.6 (2)C25—C24—C23118.6 (2)
C2—C3—H3A120.7C25—C24—H24A120.7
C4—C3—H3A120.7C23—C24—H24A120.7
C3—C4—C5121.3 (2)C24—C25—C26121.4 (2)
C3—C4—H4A119.3C24—C25—H25A119.3
C5—C4—H4A119.3C26—C25—H25A119.3
C4—C5—C6119.8 (2)C27—C26—C25120.0 (2)
C4—C5—H5A120.1C27—C26—H26A120.0
C6—C5—H5A120.1C25—C26—H26A120.0
C1—C6—C5118.5 (2)C26—C27—C22118.44 (19)
C1—C6—N1120.98 (19)C26—C27—N3120.03 (19)
C5—C6—N1120.5 (2)C22—C27—N3121.52 (18)
N1—C7—C8112.05 (17)N3—C28—C29112.28 (17)
N1—C7—C14102.14 (16)N3—C28—C35102.32 (16)
C8—C7—C14113.79 (17)C29—C28—C35113.75 (17)
N1—C7—H7A109.5N3—C28—H28A109.4
C8—C7—H7A109.5C29—C28—H28A109.4
C14—C7—H7A109.5C35—C28—H28A109.4
C9—C8—C13118.1 (2)C30—C29—C34118.0 (2)
C9—C8—C7120.9 (2)C30—C29—C28120.8 (2)
C13—C8—C7121.00 (19)C34—C29—C28121.25 (18)
C8—C9—C10119.9 (3)C29—C30—C31121.2 (2)
C8—C9—H9A120.0C29—C30—H30A119.4
C10—C9—H9A120.0C31—C30—H30A119.4
C11—C10—C9121.1 (3)C32—C31—C30120.5 (2)
C11—C10—H10A119.5C32—C31—H31A119.7
C9—C10—H10A119.5C30—C31—H31A119.7
C12—C11—C10119.4 (3)C33—C32—C31119.5 (2)
C12—C11—H11A120.3C33—C32—H32A120.2
C10—C11—H11A120.3C31—C32—H32A120.2
C11—C12—C13120.2 (3)C32—C33—C34120.0 (2)
C11—C12—H12A119.9C32—C33—H33A120.0
C13—C12—H12A119.9C34—C33—H33A120.0
C8—C13—C12121.3 (2)C29—C34—C33120.8 (2)
C8—C13—H13A119.4C29—C34—H34A119.6
C12—C13—H13A119.4C33—C34—H34A119.6
C15—C14—C7102.83 (17)C36—C35—C28102.52 (16)
C15—C14—H14A111.2C36—C35—H35A111.3
C7—C14—H14A111.2C28—C35—H35A111.3
C15—C14—H14B111.2C36—C35—H35B111.3
C7—C14—H14B111.2C28—C35—H35B111.3
H14A—C14—H14B109.1H35A—C35—H35B109.2
N2—C15—C16121.78 (18)N4—C36—C37121.32 (18)
N2—C15—C14113.18 (18)N4—C36—C35113.83 (17)
C16—C15—C14125.03 (18)C37—C36—C35124.82 (18)
C21—C16—C17117.7 (2)C42—C37—C38118.23 (19)
C21—C16—C15121.24 (19)C42—C37—C36121.21 (18)
C17—C16—C15121.06 (19)C38—C37—C36120.54 (19)
C18—C17—C16122.0 (2)C39—C38—C37121.2 (2)
C18—C17—H17A119.0C39—C38—H38A119.4
C16—C17—H17A119.0C37—C38—H38A119.4
C19—C18—C17117.9 (2)C40—C39—C38118.5 (2)
C19—C18—H18A121.0C40—C39—H39A120.8
C17—C18—H18A121.0C38—C39—H39A120.8
C18—C19—F1118.8 (2)C39—C40—F2119.1 (2)
C18—C19—C20122.6 (2)C39—C40—C41122.5 (2)
F1—C19—C20118.6 (2)F2—C40—C41118.4 (2)
C19—C20—C21118.8 (2)C42—C41—C40118.8 (2)
C19—C20—H20A120.6C42—C41—H41A120.6
C21—C20—H20A120.6C40—C41—H41A120.6
C16—C21—C20120.9 (2)C41—C42—C37120.7 (2)
C16—C21—H21A119.5C41—C42—H42A119.6
C20—C21—H21A119.5C37—C42—H42A119.6
 

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