#------------------------------------------------------------------------------
#$Date: 2024-12-04 04:57:25 +0200 (Wed, 04 Dec 2024) $
#$Revision: 296215 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/33/1573387.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1573387
loop_
_publ_author_name
'Koch, Pierre'
'Schollmeyer, Dieter'
_publ_section_title
;
 1-[(2-Chlorophenyl)diphenylmethyl]-1H-pyrazole
;
_journal_coeditor_code           HB4496
_journal_issue                   12
_journal_name_full               IUCrData
_journal_paper_doi               10.1107/S2414314624011520
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          'C22 H17 Cl N2'
_chemical_formula_moiety         'C22 H17 Cl N2'
_chemical_formula_sum            'C22 H17 Cl N2'
_chemical_formula_weight         344.82
_chemical_name_systematic
;
1-[(2-Chlorophenyl)diphenylmethyl]-1H-pyrazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 95.942(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8768(3)
_cell_length_b                   18.3002(7)
_cell_length_c                   10.5053(3)
_cell_measurement_reflns_used    21301
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.23
_cell_volume                     1697.39(10)
_computing_cell_refinement
;
X-Area Recipe 1.36.0.0 (Stoe & Cie, 2019)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (Stoe & Cie, 2019)
;
_computing_data_reduction
;
X-Area Integrate 1.77.0.0 (Stoe & Cie, 2019)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      233(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22452
_diffrn_reflns_theta_full        27.999
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'sealed Tube'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0431P)²+0.0511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                2854
_reflns_number_total             4092
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4496.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1573387
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.89682(4) 0.34060(2) 0.81219(4) 0.03752(11) Uani d 1 . .
C C1 0.58130(17) 0.42292(7) 0.75062(13) 0.0250(3) Uani d 1 . .
N N2 0.62973(14) 0.38408(6) 0.63686(11) 0.0254(3) Uani d 1 . .
N N3 0.59467(16) 0.31210(7) 0.62163(12) 0.0325(3) Uani d 1 . .
C C4 0.6549(2) 0.29284(9) 0.51660(15) 0.0360(4) Uani d 1 . .
H H4 0.648932 0.245476 0.481808 0.043 Uiso calc 1 . .
C C5 0.7282(2) 0.35090(9) 0.46361(16) 0.0399(4) Uani d 1 . .
H H5 0.778981 0.350618 0.389382 0.048 Uiso calc 1 . .
C C6 0.71009(19) 0.40817(8) 0.54324(14) 0.0326(3) Uani d 1 . .
H H6 0.746928 0.455872 0.534524 0.039 Uiso calc 1 . .
C C7 0.67484(16) 0.49371(8) 0.77271(13) 0.0257(3) Uani d 1 . .
C C8 0.77370(17) 0.50538(8) 0.88172(14) 0.0297(3) Uani d 1 . .
H H8 0.786378 0.468877 0.944871 0.036 Uiso calc 1 . .
C C9 0.85418(19) 0.57016(9) 0.89893(16) 0.0370(4) Uani d 1 . .
H H9 0.920168 0.577367 0.973789 0.044 Uiso calc 1 . .
C C10 0.8380(2) 0.62395(9) 0.80707(17) 0.0391(4) Uani d 1 . .
H H10 0.895620 0.667054 0.817139 0.047 Uiso calc 1 . .
C C11 0.7365(2) 0.61397(8) 0.70024(16) 0.0384(4) Uani d 1 . .
H H11 0.723045 0.650950 0.638004 0.046 Uiso calc 1 . .
C C12 0.65441(18) 0.54996(8) 0.68393(15) 0.0316(3) Uani d 1 . .
H H12 0.583602 0.544385 0.611624 0.038 Uiso calc 1 . .
C C13 0.41300(17) 0.44410(8) 0.72473(13) 0.0259(3) Uani d 1 . .
C C14 0.31188(18) 0.40494(8) 0.64180(15) 0.0314(3) Uani d 1 . .
H H14 0.346806 0.364934 0.597033 0.038 Uiso calc 1 . .
C C15 0.15994(19) 0.42380(9) 0.62375(16) 0.0380(4) Uani d 1 . .
H H15 0.093076 0.396539 0.566990 0.046 Uiso calc 1 . .
C C16 0.10643(19) 0.48194(9) 0.68808(15) 0.0367(4) Uani d 1 . .
H H16 0.003507 0.494899 0.675255 0.044 Uiso calc 1 . .
C C17 0.20511(19) 0.52101(9) 0.77149(15) 0.0353(4) Uani d 1 . .
H H17 0.169256 0.560687 0.816524 0.042 Uiso calc 1 . .
C C18 0.35642(18) 0.50244(9) 0.78966(15) 0.0323(3) Uani d 1 . .
H H18 0.422426 0.529778 0.847021 0.039 Uiso calc 1 . .
C C19 0.60600(17) 0.37049(7) 0.86593(13) 0.0262(3) Uani d 1 . .
C C20 0.49184(19) 0.35937(8) 0.94499(15) 0.0324(3) Uani d 1 . .
H H20 0.397746 0.382274 0.924093 0.039 Uiso calc 1 . .
C C21 0.5113(2) 0.31593(9) 1.05318(16) 0.0387(4) Uani d 1 . .
H H21 0.431234 0.309744 1.104196 0.046 Uiso calc 1 . .
C C22 0.6475(2) 0.28186(9) 1.08598(16) 0.0391(4) Uani d 1 . .
H H22 0.661712 0.252793 1.160029 0.047 Uiso calc 1 . .
C C23 0.7635(2) 0.29062(8) 1.00941(15) 0.0348(4) Uani d 1 . .
H H23 0.856956 0.267262 1.030945 0.042 Uiso calc 1 . .
C C24 0.74213(18) 0.33379(8) 0.90091(14) 0.0292(3) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C13 . . 109.46(11) ?
N2 C1 C19 . . 107.66(11) ?
C13 C1 C19 . . 110.58(11) ?
N2 C1 C7 . . 108.98(11) ?
C13 C1 C7 . . 108.19(11) ?
C19 C1 C7 . . 111.92(12) ?
C6 N2 N3 . . 111.30(12) ?
C6 N2 C1 . . 130.33(12) ?
N3 N2 C1 . . 118.34(11) ?
C4 N3 N2 . . 104.41(12) ?
N3 C4 C5 . . 112.11(14) ?
N3 C4 H4 . . 123.9 ?
C5 C4 H4 . . 123.9 ?
C6 C5 C4 . . 104.60(14) ?
C6 C5 H5 . . 127.7 ?
C4 C5 H5 . . 127.7 ?
N2 C6 C5 . . 107.58(14) ?
N2 C6 H6 . . 126.2 ?
C5 C6 H6 . . 126.2 ?
C8 C7 C12 . . 117.94(14) ?
C8 C7 C1 . . 122.59(13) ?
C12 C7 C1 . . 119.37(13) ?
C7 C8 C9 . . 120.89(15) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C10 C9 C8 . . 120.37(15) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.26(15) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 120.41(16) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C7 . . 121.00(15) ?
C11 C12 H12 . . 119.5 ?
C7 C12 H12 . . 119.5 ?
C14 C13 C18 . . 117.59(14) ?
C14 C13 C1 . . 122.33(13) ?
C18 C13 C1 . . 120.02(13) ?
C13 C14 C15 . . 121.04(15) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C16 C15 C14 . . 120.50(15) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C15 C16 C17 . . 119.18(16) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
C16 C17 C18 . . 120.50(15) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C13 . . 121.19(15) ?
C17 C18 H18 . . 119.4 ?
C13 C18 H18 . . 119.4 ?
C20 C19 C24 . . 115.87(13) ?
C20 C19 C1 . . 120.46(13) ?
C24 C19 C1 . . 123.63(13) ?
C21 C20 C19 . . 122.59(15) ?
C21 C20 H20 . . 118.7 ?
C19 C20 H20 . . 118.7 ?
C22 C21 C20 . . 119.94(15) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C23 . . 119.47(15) ?
C21 C22 H22 . . 120.3 ?
C23 C22 H22 . . 120.3 ?
C22 C23 C24 . . 119.99(15) ?
C22 C23 H23 . . 120.0 ?
C24 C23 H23 . . 120.0 ?
C23 C24 C19 . . 122.12(14) ?
C23 C24 Cl1 . . 115.68(12) ?
C19 C24 Cl1 . . 122.19(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C24 . 1.7420(16) ?
C1 N2 . 1.4915(18) ?
C1 C13 . 1.540(2) ?
C1 C19 . 1.5430(19) ?
C1 C7 . 1.5433(19) ?
N2 C6 . 1.3475(19) ?
N2 N3 . 1.3592(17) ?
N3 C4 . 1.323(2) ?
C4 C5 . 1.392(2) ?
C4 H4 . 0.9400 ?
C5 C6 . 1.361(2) ?
C5 H5 . 0.9400 ?
C6 H6 . 0.9400 ?
C7 C8 . 1.385(2) ?
C7 C12 . 1.388(2) ?
C8 C9 . 1.386(2) ?
C8 H8 . 0.9400 ?
C9 C10 . 1.376(2) ?
C9 H9 . 0.9400 ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.9400 ?
C11 C12 . 1.381(2) ?
C11 H11 . 0.9400 ?
C12 H12 . 0.9400 ?
C13 C14 . 1.384(2) ?
C13 C18 . 1.389(2) ?
C14 C15 . 1.386(2) ?
C14 H14 . 0.9400 ?
C15 C16 . 1.371(2) ?
C15 H15 . 0.9400 ?
C16 C17 . 1.374(2) ?
C16 H16 . 0.9400 ?
C17 C18 . 1.379(2) ?
C17 H17 . 0.9400 ?
C18 H18 . 0.9400 ?
C19 C20 . 1.390(2) ?
C19 C24 . 1.398(2) ?
C20 C21 . 1.383(2) ?
C20 H20 . 0.9400 ?
C21 C22 . 1.373(2) ?
C21 H21 . 0.9400 ?
C22 C23 . 1.380(2) ?
C22 H22 . 0.9400 ?
C23 C24 . 1.384(2) ?
C23 H23 . 0.9400 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 Cg3 3_666 0.94 2.93 3.5594(16) 125
C16 H16 Cg2 1_455 0.94 2.88 3.6868(18) 145
C20 H20 Cg3 1_555 0.94 2.89 3.6164(17) 135
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 N2 C6 . . . . 102.06(17) ?
C19 C1 N2 C6 . . . . -137.68(15) ?
C7 C1 N2 C6 . . . . -16.1(2) ?
C13 C1 N2 N3 . . . . -80.21(15) ?
C19 C1 N2 N3 . . . . 40.04(16) ?
C7 C1 N2 N3 . . . . 161.64(12) ?
C6 N2 N3 C4 . . . . -0.18(17) ?
C1 N2 N3 C4 . . . . -178.31(13) ?
N2 N3 C4 C5 . . . . 0.01(19) ?
N3 C4 C5 C6 . . . . 0.2(2) ?
N3 N2 C6 C5 . . . . 0.28(18) ?
C1 N2 C6 C5 . . . . 178.13(14) ?
C4 C5 C6 N2 . . . . -0.26(19) ?
N2 C1 C7 C8 . . . . -116.07(15) ?
C13 C1 C7 C8 . . . . 124.98(15) ?
C19 C1 C7 C8 . . . . 2.90(19) ?
N2 C1 C7 C12 . . . . 67.44(16) ?
C13 C1 C7 C12 . . . . -51.50(17) ?
C19 C1 C7 C12 . . . . -173.59(13) ?
C12 C7 C8 C9 . . . . -2.5(2) ?
C1 C7 C8 C9 . . . . -179.07(14) ?
C7 C8 C9 C10 . . . . -0.5(2) ?
C8 C9 C10 C11 . . . . 2.6(2) ?
C9 C10 C11 C12 . . . . -1.5(3) ?
C10 C11 C12 C7 . . . . -1.6(3) ?
C8 C7 C12 C11 . . . . 3.6(2) ?
C1 C7 C12 C11 . . . . -179.73(14) ?
N2 C1 C13 C14 . . . . 27.42(18) ?
C19 C1 C13 C14 . . . . -91.04(16) ?
C7 C1 C13 C14 . . . . 146.06(14) ?
N2 C1 C13 C18 . . . . -155.38(13) ?
C19 C1 C13 C18 . . . . 86.16(16) ?
C7 C1 C13 C18 . . . . -36.74(17) ?
C18 C13 C14 C15 . . . . 0.5(2) ?
C1 C13 C14 C15 . . . . 177.75(14) ?
C13 C14 C15 C16 . . . . 0.0(2) ?
C14 C15 C16 C17 . . . . -0.5(2) ?
C15 C16 C17 C18 . . . . 0.5(2) ?
C16 C17 C18 C13 . . . . -0.1(2) ?
C14 C13 C18 C17 . . . . -0.4(2) ?
C1 C13 C18 C17 . . . . -177.77(14) ?
N2 C1 C19 C20 . . . . -131.44(14) ?
C13 C1 C19 C20 . . . . -11.89(18) ?
C7 C1 C19 C20 . . . . 108.82(15) ?
N2 C1 C19 C24 . . . . 50.99(17) ?
C13 C1 C19 C24 . . . . 170.54(13) ?
C7 C1 C19 C24 . . . . -68.75(17) ?
C24 C19 C20 C21 . . . . 1.2(2) ?
C1 C19 C20 C21 . . . . -176.56(14) ?
C19 C20 C21 C22 . . . . 0.0(3) ?
C20 C21 C22 C23 . . . . -0.8(3) ?
C21 C22 C23 C24 . . . . 0.3(2) ?
C22 C23 C24 C19 . . . . 1.0(2) ?
C22 C23 C24 Cl1 . . . . 179.98(13) ?
C20 C19 C24 C23 . . . . -1.7(2) ?
C1 C19 C24 C23 . . . . 175.98(14) ?
C20 C19 C24 Cl1 . . . . 179.37(11) ?
C1 C19 C24 Cl1 . . . . -3.0(2) ?
