Crystal structure of 5-(4-chlorophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C21H16ClFN2
Shen, Zhenpeng; Liu, E.; Tian, Xinzhe; Jian, Fangfang; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 613–615; doi:10.1515/ncrs-2018-0553

data_8105797
_publ_section_title
;
 Crystal structure of
 5-(4-chlorophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole,
 C21H16ClFN2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              613
_journal_page_last               615
_journal_paper_doi               10.1515/ncrs-2018-0553
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C21 H16 Cl F N2'
_chemical_formula_sum            'C21 H16 Cl F N2'
_chemical_formula_weight         350.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 104.95(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.286(4)
_cell_length_b                   5.3827(11)
_cell_length_c                   16.254(3)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2
_cell_measurement_theta_min      3.01
_cell_volume                     1714.8(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker '
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_measured_fraction_theta_max 0.9957
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7677
_diffrn_reflns_theta_full        24.9993
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0255 before and 0.0165 after correction.
The Ratio of minimum to maximum transmission is 0.8995.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3589
_exptl_crystal_description       block
_exptl_crystal_F_000             728.8964
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.2115
_refine_diff_density_min         -0.2726
_refine_diff_density_rms         0.0507
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             9.7997
_refine_ls_goodness_of_fit_ref   1.0870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.0819
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.8404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -24
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2538
_reflns_number_total             3018
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_ncrs-2018-0553_suppl.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        1714.7(7)
_cod_database_code               8105797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C1-C6 \\sim C1A-C6
 with sigma of 0.02
 C2-C3 \\sim C2A-C3
 with sigma of 0.02
 C3-C4 \\sim C3-C4A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6
 with sigma of 0.02
 C1-C3 \\sim C1A-C3
 with sigma of 0.04
 C2-C6 \\sim C2A-C6
 with sigma of 0.04
 C3-C5 \\sim C3-C5A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6
 with sigma of 0.04
 C3-F1 \\sim C3-F1A
 with sigma of 0.02
 C2-F1 \\sim C4-F1 \\sim C2A-F1A \\sim C4A-F1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C5A)
Uanis(C4) = Uanis(C4A)
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(F1A) = Uanis(F1)
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=Sof(H1A)=1-
 FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=FVAR(1)
 Sof(F1A)=1-FVAR(2)
 Sof(F1)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C5A(H5A), C4A(H4A), C2A(H2A),
  C1A(H1A)
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_olex2_submission_special_instructions 'No special instructions were received'