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#$Date: 2022-03-09 12:27:25 +0200 (Wed, 09 Mar 2022) $
#$Revision: 273565 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104704.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_8104704
loop_
_publ_author_name
'Shao, Han-Qiao'
'Wang, Yin-Xin'
'Sun, Hai-Yang'
'Wang, Yu-Cai'
'Sun, Wu-Ji'
_publ_section_title
;
 Crystal structure of
 1,4-bis(4-bromobenzyl)-4-(4-chlorophenyl)-1,4-dihydropyridine-3-carbonitrile,
 C26H19Br2ClN2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              763
_journal_page_last               765
_journal_paper_doi               10.1515/ncrs-2021-0068
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C26 H19 Br2 Cl N2'
_chemical_formula_sum            'C26 H19 Br2 Cl N2'
_chemical_formula_weight         554.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                111.234(2)
_cell_angle_beta                 98.025(2)
_cell_angle_gamma                101.707(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4830(12)
_cell_length_b                   10.2313(12)
_cell_length_c                   13.5948(18)
_cell_measurement_reflns_used    1944
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.09
_cell_volume                     1170.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6017
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.466
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.593
_exptl_absorpt_correction_T_max  0.564
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0700P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2659
_reflns_number_total             4093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0068_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104704
_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   0.492
_shelx_estimated_absorpt_t_max   0.564
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17965(6) -0.35193(5) 0.11636(5) 0.0797(2) Uani 1 1 d . . . . .
Br2 Br 0.67877(6) -0.35025(5) -0.02730(5) 0.0887(2) Uani 1 1 d . . . . .
C1 C 1.1809(5) -0.1564(4) 0.1957(3) 0.0504(10) Uani 1 1 d . . . . .
C2 C 1.3033(5) -0.0638(5) 0.2763(4) 0.0602(12) Uani 1 1 d . . . . .
H2 H 1.383229 -0.097581 0.293601 0.072 Uiso 1 1 calc R U . . .
C3 C 1.3059(5) 0.0789(5) 0.3309(3) 0.0565(11) Uani 1 1 d . . . . .
H3 H 1.388527 0.141614 0.385395 0.068 Uiso 1 1 calc R U . . .
C4 C 1.1883(4) 0.1318(4) 0.3067(3) 0.0445(9) Uani 1 1 d . . . . .
C5 C 1.0664(5) 0.0355(5) 0.2270(3) 0.0585(12) Uani 1 1 d . . . . .
H5 H 0.985221 0.068074 0.210377 0.070 Uiso 1 1 calc R U . . .
C6 C 1.0622(5) -0.1069(4) 0.1718(4) 0.0622(12) Uani 1 1 d . . . . .
H6 H 0.978948 -0.170232 0.118120 0.075 Uiso 1 1 calc R U . . .
C7 C 1.1986(5) 0.2892(4) 0.3704(4) 0.0611(12) Uani 1 1 d . . . . .
H7A H 1.214411 0.307240 0.446825 0.073 Uiso 1 1 calc R U . . .
H7B H 1.284500 0.349228 0.361050 0.073 Uiso 1 1 calc R U . . .
C8 C 0.9575(4) 0.3312(4) 0.3923(3) 0.0423(9) Uani 1 1 d . . . . .
H8 H 0.968981 0.305939 0.451529 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3621(3) 0.3633(3) 0.0379(9) 0.04 Uani 1 1 d . . . . .
C10 C 0.7975(4) 0.4019(4) 0.2664(3) 0.0422(9) Uani 1 1 d . . . . .
C11 C 0.9288(5) 0.4009(4) 0.2158(3) 0.0530(11) Uani 1 1 d . . . . .
H11 H 0.924613 0.423173 0.155157 0.064 Uiso 1 1 calc R U . . .
C12 C 1.0499(5) 0.3704(4) 0.2517(3) 0.0522(10) Uani 1 1 d . . . . .
H12 H 1.125874 0.373203 0.215401 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7248(5) 0.3554(4) 0.4258(3) 0.0467(10) Uani 1 1 d . . . . .
C14 C 0.7736(4) 0.5557(4) 0.3063(3) 0.0438(9) Uani 1 1 d . . . . .
C15 C 0.6381(5) 0.5809(4) 0.3239(3) 0.0528(11) Uani 1 1 d . . . . .
H15 H 0.557719 0.501221 0.307738 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6187(5) 0.7177(4) 0.3640(3) 0.0578(11) Uani 1 1 d . . . . .
H16 H 0.526779 0.730531 0.374585 0.069 Uiso 1 1 calc R U . . .
C17 C 0.7380(5) 0.8369(4) 0.3887(3) 0.0536(11) Uani 1 1 d . . . . .
C18 C 0.8722(5) 0.8180(4) 0.3733(3) 0.0593(12) Uani 1 1 d . . . . .
H18 H 0.951673 0.898466 0.389428 0.071 Uiso 1 1 calc R U . . .
C19 C 0.8907(5) 0.6778(4) 0.3332(3) 0.0531(10) Uani 1 1 d . . . . .
H19 H 0.983463 0.666126 0.324449 0.064 Uiso 1 1 calc R U . . .
C20 C 0.6781(4) -0.1517(4) 0.0382(3) 0.0538(11) Uani 1 1 d . . . . .
C21 C 0.7218(6) -0.0596(5) -0.0093(4) 0.0702(13) Uani 1 1 d . . . . .
H21 H 0.754525 -0.092189 -0.072939 0.084 Uiso 1 1 calc R U . . .
C22 C 0.7171(5) 0.0838(5) 0.0381(3) 0.0652(13) Uani 1 1 d . . . . .
H22 H 0.747291 0.146973 0.005407 0.078 Uiso 1 1 calc R U . . .
C23 C 0.6692(4) 0.1350(4) 0.1317(3) 0.0467(10) Uani 1 1 d . . . . .
C24 C 0.6283(5) 0.0393(4) 0.1786(3) 0.0587(11) Uani 1 1 d . . . . .
H24 H 0.597341 0.072132 0.242972 0.070 Uiso 1 1 calc R U . . .
C25 C 0.6317(5) -0.1047(4) 0.1330(4) 0.0631(12) Uani 1 1 d . . . . .
H25 H 0.603221 -0.168006 0.165849 0.076 Uiso 1 1 calc R U . . .
C26 C 0.6566(5) 0.2892(4) 0.1801(3) 0.0544(11) Uani 1 1 d . . . . .
H26A H 0.572856 0.289083 0.213708 0.065 Uiso 1 1 calc R U . . .
H26B H 0.635981 0.321094 0.121861 0.065 Uiso 1 1 calc R U . . .
Cl1 Cl 0.71559(16) 1.01196(11) 0.43980(10) 0.0775(4) Uani 1 1 d . . . . .
N1 N 1.0690(4) 0.3347(3) 0.3405(3) 0.0484(8) Uani 1 1 d . . . . .
N2 N 0.6382(5) 0.3502(4) 0.4761(3) 0.0708(11) Uani 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 120.3(4) . .
C6 C1 Br1 120.4(3) . .
C2 C1 Br1 119.3(3) . .
C3 C2 C1 119.1(4) . .
C3 C2 H2 120.4 . .
C1 C2 H2 120.4 . .
C2 C3 C4 121.5(4) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C5 C4 C3 117.8(4) . .
C5 C4 C7 123.6(4) . .
C3 C4 C7 118.5(3) . .
C6 C5 C4 121.4(4) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C5 C6 C1 119.9(4) . .
C5 C6 H6 120.1 . .
C1 C6 H6 120.1 . .
N1 C7 C4 114.7(3) . .
N1 C7 H7A 108.6 . .
C4 C7 H7A 108.6 . .
N1 C7 H7B 108.6 . .
C4 C7 H7B 108.6 . .
H7A C7 H7B 107.6 . .
C9 C8 N1 123.9(4) . .
C9 C8 H8 118.1 . .
N1 C8 H8 118.1 . .
C8 C9 C13 117.6(4) . .
C8 C9 C10 123.2(3) . .
C13 C9 C10 119.2(3) . .
C11 C10 C9 107.6(3) . .
C11 C10 C14 109.9(3) . .
C9 C10 C14 109.2(3) . .
C11 C10 C26 109.1(3) . .
C9 C10 C26 111.2(3) . .
C14 C10 C26 109.7(3) . .
C12 C11 C10 124.5(4) . .
C12 C11 H11 117.7 . .
C10 C11 H11 117.7 . .
C11 C12 N1 123.2(4) . .
C11 C12 H12 118.4 . .
N1 C12 H12 118.4 . .
N2 C13 C9 179.6(5) . .
C19 C14 C15 116.5(4) . .
C19 C14 C10 120.6(4) . .
C15 C14 C10 122.7(3) . .
C16 C15 C14 122.8(4) . .
C16 C15 H15 118.6 . .
C14 C15 H15 118.6 . .
C15 C16 C17 119.0(4) . .
C15 C16 H16 120.5 . .
C17 C16 H16 120.5 . .
C18 C17 C16 120.4(4) . .
C18 C17 Cl1 119.9(3) . .
C16 C17 Cl1 119.7(4) . .
C17 C18 C19 120.0(4) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C14 C19 C18 121.4(4) . .
C14 C19 H19 119.3 . .
C18 C19 H19 119.3 . .
C21 C20 C25 121.1(4) . .
C21 C20 Br2 120.0(3) . .
C25 C20 Br2 118.9(3) . .
C20 C21 C22 119.2(4) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
C23 C22 C21 121.7(4) . .
C23 C22 H22 119.1 . .
C21 C22 H22 119.1 . .
C22 C23 C24 117.4(4) . .
C22 C23 C26 121.7(4) . .
C24 C23 C26 120.9(4) . .
C23 C24 C25 122.1(4) . .
C23 C24 H24 119.0 . .
C25 C24 H24 119.0 . .
C20 C25 C24 118.4(4) . .
C20 C25 H25 120.8 . .
C24 C25 H25 120.8 . .
C23 C26 C10 114.6(3) . .
C23 C26 H26A 108.6 . .
C10 C26 H26A 108.6 . .
C23 C26 H26B 108.6 . .
C10 C26 H26B 108.6 . .
H26A C26 H26B 107.6 . .
C8 N1 C12 117.6(3) . .
C8 N1 C7 121.3(4) . .
C12 N1 C7 120.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.895(4) .
Br2 C20 1.902(4) .
C1 C6 1.370(6) .
C1 C2 1.376(6) .
C2 C3 1.370(6) .
C2 H2 0.9300 .
C3 C4 1.384(5) .
C3 H3 0.9300 .
C4 C5 1.377(5) .
C4 C7 1.502(5) .
C5 C6 1.365(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N1 1.457(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.342(5) .
C8 N1 1.351(5) .
C8 H8 0.9300 .
C9 C13 1.413(6) .
C9 C10 1.526(5) .
C10 C11 1.504(6) .
C10 C14 1.544(5) .
C10 C26 1.565(5) .
C11 C12 1.324(6) .
C11 H11 0.9300 .
C12 N1 1.381(5) .
C12 H12 0.9300 .
C13 N2 1.145(5) .
C14 C19 1.386(5) .
C14 C15 1.396(5) .
C15 C16 1.368(5) .
C15 H15 0.9300 .
C16 C17 1.385(6) .
C16 H16 0.9300 .
C17 C18 1.358(6) .
C17 Cl1 1.740(4) .
C18 C19 1.396(6) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C21 1.354(6) .
C20 C25 1.371(6) .
C21 C22 1.385(6) .
C21 H21 0.9300 .
C22 C23 1.370(6) .
C22 H22 0.9300 .
C23 C24 1.371(6) .
C23 C26 1.511(5) .
C24 C25 1.385(6) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 Br2 0.93 3.01 3.930(4) 169.8 . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.2(7) . . . .
Br1 C1 C2 C3 177.7(3) . . . .
C1 C2 C3 C4 0.0(7) . . . .
C2 C3 C4 C5 1.2(6) . . . .
C2 C3 C4 C7 179.5(4) . . . .
C3 C4 C5 C6 -1.3(7) . . . .
C7 C4 C5 C6 -179.5(4) . . . .
C4 C5 C6 C1 0.2(7) . . . .
C2 C1 C6 C5 1.1(7) . . . .
Br1 C1 C6 C5 -177.7(3) . . . .
C5 C4 C7 N1 -1.0(6) . . . .
C3 C4 C7 N1 -179.2(4) . . . .
N1 C8 C9 C13 -179.4(3) . . . .
N1 C8 C9 C10 1.3(5) . . . .
C8 C9 C10 C11 -0.8(5) . . . .
C13 C9 C10 C11 179.9(3) . . . .
C8 C9 C10 C14 -120.1(4) . . . .
C13 C9 C10 C14 60.6(4) . . . .
C8 C9 C10 C26 118.7(4) . . . .
C13 C9 C10 C26 -60.6(4) . . . .
C9 C10 C11 C12 -0.1(5) . . . .
C14 C10 C11 C12 118.7(4) . . . .
C26 C10 C11 C12 -120.9(4) . . . .
C10 C11 C12 N1 0.5(6) . . . .
C11 C10 C14 C19 -25.5(5) . . . .
C9 C10 C14 C19 92.3(4) . . . .
C26 C10 C14 C19 -145.6(4) . . . .
C11 C10 C14 C15 158.7(4) . . . .
C9 C10 C14 C15 -83.4(4) . . . .
C26 C10 C14 C15 38.7(5) . . . .
C19 C14 C15 C16 1.0(6) . . . .
C10 C14 C15 C16 176.9(4) . . . .
C14 C15 C16 C17 -0.2(6) . . . .
C15 C16 C17 C18 0.0(6) . . . .
C15 C16 C17 Cl1 -180.0(3) . . . .
C16 C17 C18 C19 -0.5(6) . . . .
Cl1 C17 C18 C19 179.4(3) . . . .
C15 C14 C19 C18 -1.6(6) . . . .
C10 C14 C19 C18 -177.5(4) . . . .
C17 C18 C19 C14 1.4(6) . . . .
C25 C20 C21 C22 -1.0(7) . . . .
Br2 C20 C21 C22 178.4(4) . . . .
C20 C21 C22 C23 -0.1(8) . . . .
C21 C22 C23 C24 1.2(7) . . . .
C21 C22 C23 C26 -176.8(4) . . . .
C22 C23 C24 C25 -1.3(7) . . . .
C26 C23 C24 C25 176.7(4) . . . .
C21 C20 C25 C24 1.0(7) . . . .
Br2 C20 C25 C24 -178.5(3) . . . .
C23 C24 C25 C20 0.2(7) . . . .
C22 C23 C26 C10 -92.4(5) . . . .
C24 C23 C26 C10 89.7(5) . . . .
C11 C10 C26 C23 57.2(4) . . . .
C9 C10 C26 C23 -61.4(4) . . . .
C14 C10 C26 C23 177.7(3) . . . .
C9 C8 N1 C12 -0.9(5) . . . .
C9 C8 N1 C7 -175.2(3) . . . .
C11 C12 N1 C8 0.0(6) . . . .
C11 C12 N1 C7 174.3(4) . . . .
C4 C7 N1 C8 92.7(4) . . . .
C4 C7 N1 C12 -81.4(5) . . . .
