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#$Date: 2022-05-11 11:04:26 +0300 (Wed, 11 May 2022) $
#$Revision: 275326 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105213.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_8105213
loop_
_publ_author_name
'Zhang, Lilei'
'Cheng, Tianyu'
_publ_section_title
;
 The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline,
 C14H9BrClN2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              311
_journal_page_last               313
_journal_paper_doi               10.1515/ncrs-2022-0008
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H8 Br Cl N2'
_chemical_formula_sum            'C14 H8 Br Cl N2'
_chemical_formula_weight         319.58
_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     dual
_cell_angle_alpha                90
_cell_angle_beta                 97.861(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1347(11)
_cell_length_b                   3.8441(2)
_cell_length_c                   18.4127(12)
_cell_measurement_reflns_used    3544
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.23
_cell_volume                     1201.40(13)
_computing_cell_refinement       'SAINT V8.40A (?, 2016) [1]'
_computing_data_collection       'SAINT V8.40A (?, 2016) [1]'
_computing_data_reduction        'SAINT V8.40A (?, 2016) [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [4]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [3]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [2]'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12671
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.509
_diffrn_reflns_theta_min         2.233
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.623
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0999 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.7990. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0388
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1895
_reflns_number_total             2469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0008_suppl.cif
_cod_data_source_block           mo_22020065_0m
_cod_database_code               8105213
_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_max   0.760
_shelx_estimated_absorpt_t_min   0.612
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C10(H10), C7(H7), C13(H13), C14(H14), C4(H4), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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 0.37170(2) 0.66309(11) 0.87227(2) 0.03856(19) Uani 1 1 d . . . . .
C1 C 0.4771(2) 0.5789(10) 0.7680(2) 0.0294(8) Uani 1 1 d . . . . .
H1 H 0.514521 0.682332 0.804515 0.035 Uiso 1 1 calc R . . . .
C2 C 0.4994(2) 0.4754(10) 0.70059(19) 0.0273(8) Uani 1 1 d . . . . .
C3 C 0.4430(2) 0.3159(9) 0.64800(19) 0.0267(8) Uani 1 1 d . . . . .
C4 C 0.3647(2) 0.2718(10) 0.6626(2) 0.0327(9) Uani 1 1 d . . . . .
H4 H 0.326420 0.169797 0.626665 0.039 Uiso 1 1 calc R . . . .
C5 C 0.3441(2) 0.3757(9) 0.7283(2) 0.0330(9) Uani 1 1 d . . . . .
H5 H 0.291675 0.344814 0.738596 0.040 Uiso 1 1 calc R . . . .
C6 C 0.4015(2) 0.5294(10) 0.78053(19) 0.0296(8) Uani 1 1 d . . . . .
C7 C 0.5366(2) 0.2501(10) 0.5724(2) 0.0292(8) Uani 1 1 d . . . . .
H7 H 0.552724 0.172374 0.527811 0.035 Uiso 1 1 calc R . . . .
C8 C 0.5938(2) 0.4167(9) 0.62477(19) 0.0251(8) Uani 1 1 d . . . . .
C9 C 0.6756(2) 0.4743(10) 0.60847(19) 0.0263(8) Uani 1 1 d . . . . .
C10 C 0.7310(2) 0.6244(9) 0.6621(2) 0.0278(8) Uani 1 1 d . . . . .
H10 H 0.715567 0.690231 0.707804 0.033 Uiso 1 1 calc R . . . .
C11 C 0.8080(2) 0.6787(10) 0.6498(2) 0.0308(8) Uani 1 1 d . . . . .
H11 H 0.845049 0.784634 0.686239 0.037 Uiso 1 1 calc R . . . .
C12 C 0.8301(2) 0.5763(10) 0.5835(2) 0.0296(8) Uani 1 1 d . . . . .
C13 C 0.7768(2) 0.4293(11) 0.5296(2) 0.0320(9) Uani 1 1 d . . . . .
H13 H 0.792527 0.364877 0.483959 0.038 Uiso 1 1 calc R . . . .
C14 C 0.6996(2) 0.3756(9) 0.5424(2) 0.0306(9) Uani 1 1 d . . . . .
H14 H 0.662893 0.270396 0.505580 0.037 Uiso 1 1 calc R . . . .
Cl1 Cl 0.92654(6) 0.6448(3) 0.56695(6) 0.0400(3) Uani 1 1 d . . . . .
N1 N 0.46344(18) 0.1985(8) 0.58250(17) 0.0292(7) Uani 1 1 d . . . . .
N2 N 0.57492(17) 0.5262(8) 0.68817(15) 0.0266(7) 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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 '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
C8 N2 C2 117.1(3) . .
C7 N1 C3 116.0(3) . .
N2 C8 C9 118.7(3) . .
N2 C8 C7 120.7(3) . .
C7 C8 C9 120.5(3) . .
N2 C2 C3 121.7(3) . .
N2 C2 C1 119.2(3) . .
C1 C2 C3 119.1(3) . .
C10 C9 C8 119.1(3) . .
C14 C9 C8 122.3(3) . .
C14 C9 C10 118.6(3) . .
N1 C3 C2 120.7(3) . .
N1 C3 C4 119.3(3) . .
C2 C3 C4 120.0(3) . .
C1 C6 Br1 119.4(3) . .
C1 C6 C5 122.4(3) . .
C5 C6 Br1 118.2(3) . .
C2 C1 H1 120.3 . .
C6 C1 C2 119.3(3) . .
C6 C1 H1 120.3 . .
C10 C11 H11 120.5 . .
C12 C11 H11 120.5 . .
C12 C11 C10 118.9(3) . .
C9 C10 H10 119.5 . .
C11 C10 C9 121.1(4) . .
C11 C10 H10 119.5 . .
N1 C7 C8 123.7(3) . .
N1 C7 H7 118.2 . .
C8 C7 H7 118.2 . .
C12 C13 H13 120.3 . .
C12 C13 C14 119.5(4) . .
C14 C13 H13 120.3 . .
C11 C12 Cl1 119.5(3) . .
C13 C12 Cl1 119.3(3) . .
C13 C12 C11 121.2(4) . .
C9 C14 C13 120.7(3) . .
C9 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C3 C4 H4 120.0 . .
C5 C4 C3 120.0(4) . .
C5 C4 H4 120.0 . .
C6 C5 H5 120.5 . .
C4 C5 C6 119.1(4) . .
C4 C5 H5 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C6 1.901(4) .
Cl1 C12 1.741(4) .
N2 C8 1.322(5) .
N2 C2 1.359(5) .
N1 C3 1.377(5) .
N1 C7 1.308(5) .
C8 C9 1.491(5) .
C8 C7 1.428(5) .
C2 C3 1.411(5) .
C2 C1 1.405(5) .
C9 C10 1.397(5) .
C9 C14 1.389(5) .
C3 C4 1.414(5) .
C6 C1 1.360(5) .
C6 C5 1.409(5) .
C1 H1 0.9500 .
C11 H11 0.9500 .
C11 C10 1.385(5) .
C11 C12 1.383(5) .
C10 H10 0.9500 .
C7 H7 0.9500 .
C13 H13 0.9500 .
C13 C12 1.376(5) .
C13 C14 1.389(5) .
C14 H14 0.9500 .
C4 H4 0.9500 .
C4 C5 1.365(5) .
C5 H5 0.9500 .
