#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:43:43 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277998 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105797.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105797
loop_
_publ_author_name
'Shen, Zhenpeng'
'Liu, E.'
'Tian, Xinzhe'
'Jian, Fangfang'
_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 für 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       'ω 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 λ/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/[σ²(Fo²)+(0.0396P)²+0.8404P] where P=(Fo²+2Fc²)/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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
_atom_site_disorder_group
Cl1 Cl 0.43470(3) 0.30969(16) 0.31529(5) 0.0811(3) Uani 1.000000 . .
F1 F 1.0298(2) 1.0103(18) 0.3097(6) 0.0895(19) Uani 0.75(2) D 1
N1 N 0.82071(9) 0.5463(4) 0.49712(12) 0.0517(5) Uani 1.000000 . .
N2 N 0.76022(9) 0.5170(4) 0.51958(12) 0.0544(5) Uani 1.000000 . .
C1 C 0.8629(5) 0.9861(19) 0.3472(4) 0.0549(18) Uani 0.632(4) D 1
H1 H 0.8202(5) 1.0575(19) 0.3255(4) 0.066(2) Uiso 0.632(4) R 1
C2 C 0.9177(5) 1.057(2) 0.3150(6) 0.062(2) Uani 0.632(4) D 1
H2 H 0.9117(5) 1.174(2) 0.2718(6) 0.074(3) Uiso 0.632(4) R 1
C3 C 0.97817(13) 0.9547(6) 0.34690(19) 0.0776(9) Uani 1.000000 D .
C4 C 0.9823(2) 0.7227(10) 0.3853(3) 0.0719(13) Uani 0.632(4) D 1
H4 H 1.0194(2) 0.6186(10) 0.3882(3) 0.0863(16) Uiso 0.632(4) R 1
C5 C 0.9292(2) 0.6521(9) 0.4191(3) 0.0617(11) Uani 0.632(4) D 1
H5 H 0.9311(2) 0.5003(9) 0.4470(3) 0.0740(14) Uiso 0.632(4) R 1
C6 C 0.87196(11) 0.8094(4) 0.41158(14) 0.0523(6) Uani 1.000000 D .
C7 C 0.81574(11) 0.7330(4) 0.44693(13) 0.0472(5) Uani 1.000000 . .
C8 C 0.74809(11) 0.8621(4) 0.43008(14) 0.0503(6) Uani 1.000000 . .
H8a H 0.75362(11) 1.0362(4) 0.44573(14) 0.0604(7) Uiso 1.000000 R .
H8b H 0.72336(11) 0.8488(4) 0.37060(14) 0.0604(7) Uiso 1.000000 R .
C9 C 0.71143(11) 0.7203(4) 0.48749(14) 0.0495(5) Uani 1.000000 . .
H9 H 0.70779(11) 0.8268(4) 0.53503(14) 0.0594(7) Uiso 1.000000 R .
C10 C 0.75801(11) 0.3575(4) 0.58632(13) 0.0484(5) Uani 1.000000 . .
C11 C 0.80963(12) 0.1855(4) 0.61664(14) 0.0546(6) Uani 1.000000 . .
H11 H 0.84770(12) 0.1830(4) 0.59476(14) 0.0655(7) Uiso 1.000000 R .
C12 C 0.80461(13) 0.0193(5) 0.67884(16) 0.0649(7) Uani 1.000000 . .
H12 H 0.83935(13) -0.0957(5) 0.69846(16) 0.0778(8) Uiso 1.000000 R .
C13 C 0.74903(15) 0.0201(5) 0.71255(16) 0.0713(8) Uani 1.000000 . .
H13 H 0.74571(15) -0.0944(5) 0.75413(16) 0.0855(9) Uiso 1.000000 R .
C14 C 0.69855(13) 0.1926(6) 0.68389(16) 0.0676(7) Uani 1.000000 . .
H14 H 0.66114(13) 0.1964(6) 0.70703(16) 0.0811(9) Uiso 1.000000 R .
C15 C 0.70248(12) 0.3601(5) 0.62135(15) 0.0592(6) Uani 1.000000 . .
H15 H 0.66775(12) 0.4756(5) 0.60250(15) 0.0711(8) Uiso 1.000000 R .
C16 C 0.64149(11) 0.6230(4) 0.44214(13) 0.0452(5) Uani 1.000000 . .
C17 C 0.63451(12) 0.4210(4) 0.38826(15) 0.0554(6) Uani 1.000000 . .
H17 H 0.67329(12) 0.3477(4) 0.37842(15) 0.0665(7) Uiso 1.000000 R .
C18 C 0.57143(12) 0.3260(5) 0.34892(15) 0.0590(6) Uani 1.000000 . .
H18 H 0.56747(12) 0.1881(5) 0.31348(15) 0.0708(8) Uiso 1.000000 R .
C19 C 0.51450(12) 0.4369(5) 0.36256(15) 0.0542(6) Uani 1.000000 . .
C20 C 0.51948(12) 0.6426(5) 0.41321(17) 0.0622(7) Uani 1.000000 . .
H20 H 0.48042(12) 0.7197(5) 0.42075(17) 0.0747(8) Uiso 1.000000 R .
C21 C 0.58328(12) 0.7342(5) 0.45296(15) 0.0556(6) Uani 1.000000 . .
H21 H 0.58698(12) 0.8736(5) 0.48766(15) 0.0667(7) Uiso 1.000000 R .
C5A C 0.9395(4) 0.7611(16) 0.4582(6) 0.0617(11) Uani 0.368(4) D 2
H5A H 0.9477(4) 0.6777(16) 0.5100(6) 0.0740(14) Uiso 0.368(4) R 2
C4A C 0.9936(5) 0.8366(18) 0.4277(6) 0.0719(13) Uani 0.368(4) D 2
H4A H 1.0384(5) 0.8111(18) 0.4588(6) 0.0863(16) Uiso 0.368(4) R 2
C2A C 0.9231(9) 1.106(4) 0.3388(11) 0.062(2) Uani 0.368(4) D 2
H2A H 0.9208(9) 1.258(4) 0.3112(11) 0.074(3) Uiso 0.368(4) R 2
C1A C 0.8713(10) 1.027(4) 0.3721(9) 0.0549(18) Uani 0.368(4) D 2
H1A H 0.8338(10) 1.131(4) 0.3670(9) 0.066(2) Uiso 0.368(4) R 2
F1A F 1.0355(7) 1.088(4) 0.3387(13) 0.0895(19) Uani 0.25(2) D 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N1 N2 109.24(18) . .
C9 N2 N1 112.54(17) . .
C10 N2 N1 119.15(18) . .
C10 N2 C9 125.32(18) . .
C2 C3 F1 118.2(5) . .
C4 C3 F1 115.5(4) . .
C4 C3 C2 119.5(6) . .
C2A C3 C4A 109.7(9) . .
F1A C3 C4A 109.1(8) . .
F1A C3 C2A 111.4(12) . .
C5 C6 C1 114.8(5) . .
C1A C6 C5A 107.9(9) . .
C6 C7 N1 122.0(2) . .
C8 C7 N1 113.43(19) . .
C8 C7 C6 124.6(2) . .
C9 C8 C7 102.85(17) . .
C8 C9 N2 101.36(16) . .
C16 C9 N2 111.96(19) . .
C16 C9 C8 114.55(18) . .
C11 C10 N2 120.9(2) . .
C15 C10 N2 120.4(2) . .
C15 C10 C11 118.6(2) . .
C12 C11 C10 120.2(2) . .
C13 C12 C11 121.0(2) . .
C14 C13 C12 119.0(2) . .
C15 C14 C13 120.9(2) . .
C14 C15 C10 120.3(2) . .
C17 C16 C9 120.76(19) . .
C21 C16 C9 121.0(2) . .
C21 C16 C17 118.2(2) . .
C18 C17 C16 121.3(2) . .
C19 C18 C17 119.1(2) . .
C18 C19 Cl1 119.0(2) . .
C20 C19 Cl1 119.95(19) . .
C20 C19 C18 121.1(2) . .
C21 C20 C19 119.1(2) . .
C20 C21 C16 121.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C19 1.743(2) .
F1 C3 1.370(5) .
N1 N2 1.377(2) .
N1 C7 1.282(3) .
N2 C9 1.478(3) .
N2 C10 1.393(3) .
C1 C2 1.398(12) .
C1 C6 1.390(10) .
C2 C3 1.322(11) .
C3 C4 1.389(6) .
C3 C4A 1.419(9) .
C3 C2A 1.359(19) .
C3 F1A 1.403(14) .
C4 C5 1.382(6) .
C5 C6 1.417(5) .
C6 C7 1.462(3) .
C6 C5A 1.409(9) .
C6 C1A 1.33(2) .
C7 C8 1.499(3) .
C8 C9 1.538(3) .
C9 C16 1.513(3) .
C10 C11 1.389(3) .
C10 C15 1.387(3) .
C11 C12 1.373(3) .
C12 C13 1.375(4) .
C13 C14 1.372(4) .
C14 C15 1.376(3) .
C16 C17 1.380(3) .
C16 C21 1.375(3) .
C17 C18 1.373(3) .
C18 C19 1.368(3) .
C19 C20 1.368(3) .
C20 C21 1.380(3) .
C5A C4A 1.376(11) .
C2A C1A 1.37(2) .
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C1 C2 1 1
C1 C3 1 7
C1 C6 1 2
C2 F1 1 12
C2 C3 1 3
C2 C6 1 8
C3 F1 1 11
C3 C4 1 4
C3 C5 1 9
C3 C5A 1 9
C3 C4A 1 4
C3 F1A 1 11
C4 F1 1 12
C4 C5 1 5
C4 C6 1 10
C5 C6 1 6
C5A C6 1 6
C4A C6 1 10
C4A C5A 1 5
C4A F1A 1 12
C2A C3 1 3
C2A C6 1 8
C2A F1A 1 12
C1A C3 1 7
C1A C6 1 2
C1A C2A 1 1
loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.3829 0.0156 0.0156
2 0.0200 1.3624 0.0279 0.0279
3 0.0200 1.3406 0.0187 0.0187
4 0.0200 1.4043 0.0149 0.0149
5 0.0200 1.3787 0.0031 0.0031
6 0.0200 1.4130 0.0039 0.0039
7 0.0400 2.3430 0.0031 0.0031
8 0.0400 2.3980 0.0204 0.0204
9 0.0400 2.3794 0.0090 0.0090
10 0.0400 2.4230 0.0061 0.0061
11 0.0200 1.3867 0.0165 0.0165
12 0.0200 2.3067 0.0189 0.0278
