#------------------------------------------------------------------------------
#$Date: 2018-11-17 05:34:44 +0200 (Sat, 17 Nov 2018) $
#$Revision: 212032 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108312.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_2108312
loop_
_publ_author_name
'Mondal, Pradip Kumar'
'Shukla, Rahul'
'Biswas, Subha'
'Chopra, Deepak'
_publ_section_title
;
 Role of halogen-involved intermolecular interactions and existence of
 isostructurality in the crystal packing of ---CF₃ and halogen (Cl or Br
 or I) substituted benzamides
;
_journal_coeditor_code           AW5013
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520618013422
_journal_volume                  74
_journal_year                    2018
_chemical_formula_sum            'C14 H9 Br F3 N O'
_chemical_formula_weight         344.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8062(3)
_cell_length_b                   19.3000(7)
_cell_length_c                   8.8433(3)
_cell_measurement_reflns_used    7931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.43
_cell_measurement_theta_min      2.81
_cell_volume                     1332.33(8)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7418
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        24.987
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.815
_exptl_absorpt_coefficient_mu    3.114
_exptl_absorpt_correction_T_max  0.6876
_exptl_absorpt_correction_T_min  0.4174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       Needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0221
_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)+(0.0237P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0566
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                2170
_reflns_number_total             2239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5013sup1.cif
_cod_data_source_block           PB32
_cod_database_code               2108312
_shelx_shelxl_version_number     2016/6
_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   0.417
_shelx_estimated_absorpt_t_max   0.688
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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
Br1 Br 0.06621(4) 0.96805(2) 0.53181(7) 0.01863(13) Uani 1 1 d . .
F1 F 0.3000(3) 0.53012(10) 0.8649(3) 0.0397(7) Uani 1 1 d . .
F2 F 0.3967(4) 0.59822(13) 0.6928(3) 0.0363(6) Uani 1 1 d . .
F3 F 0.1839(3) 0.62966(12) 0.8313(3) 0.0316(5) Uani 1 1 d . .
O1 O 0.3933(3) 0.75529(13) 0.7431(3) 0.0212(6) Uani 1 1 d . .
N1 N 0.2360(4) 0.78380(13) 0.9515(3) 0.0154(6) Uani 1 1 d . .
H1 H 0.211(4) 0.7707(15) 1.047(5) 0.004(8) Uiso 1 1 d . .
C14 C 0.3358(5) 0.59697(19) 0.8348(4) 0.0250(8) Uani 1 1 d . .
C2 C 0.4557(4) 0.62757(17) 0.9485(4) 0.0160(7) Uani 1 1 d . .
C1 C 0.4620(4) 0.69910(17) 0.9742(4) 0.0141(7) Uani 1 1 d . .
C6 C 0.5718(4) 0.72505(19) 1.0828(4) 0.0156(8) Uani 1 1 d . .
H6 H 0.573376 0.773400 1.102861 0.019 Uiso 1 1 calc R U
C5 C 0.6802(5) 0.68125(19) 1.1630(4) 0.0218(8) Uani 1 1 d . .
H5 H 0.757673 0.699693 1.235371 0.026 Uiso 1 1 calc R U
C4 C 0.6744(5) 0.6107(2) 1.1367(4) 0.0247(8) Uani 1 1 d . .
H4 H 0.748331 0.580606 1.191183 0.030 Uiso 1 1 calc R U
C3 C 0.5615(4) 0.58368(16) 1.0316(7) 0.0218(7) Uani 1 1 d . .
H3 H 0.556091 0.535027 1.015977 0.026 Uiso 1 1 calc R U
C7 C 0.3596(4) 0.74863(16) 0.8775(4) 0.0155(7) Uani 1 1 d . .
C8 C 0.1099(5) 0.82671(16) 0.8824(4) 0.0150(7) Uani 1 1 d . .
C13 C -0.0554(4) 0.82287(19) 0.9391(4) 0.0184(8) Uani 1 1 d . .
H13 H -0.080948 0.793147 1.021731 0.022 Uiso 1 1 calc R U
C12 C -0.1830(4) 0.86287(17) 0.8740(4) 0.0180(7) Uani 1 1 d . .
H12 H -0.296181 0.860487 0.913200 0.022 Uiso 1 1 calc R U
C11 C -0.1492(4) 0.90623(16) 0.7529(4) 0.0171(7) Uani 1 1 d . .
H11 H -0.237607 0.932905 0.707497 0.021 Uiso 1 1 calc R U
C10 C 0.0175(5) 0.90954(16) 0.6999(4) 0.0151(7) Uani 1 1 d . .
C9 C 0.1490(4) 0.87115(16) 0.7643(4) 0.0136(7) Uani 1 1 d . .
H9 H 0.263226 0.875245 0.728211 0.016 Uiso 1 1 calc R U
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C7 N1 C8 125.4(3)
C7 N1 H1 118(2)
C8 N1 H1 115(2)
F2 C14 F3 106.4(3)
F2 C14 F1 106.0(3)
F3 C14 F1 105.8(3)
F2 C14 C2 113.6(3)
F3 C14 C2 112.5(3)
F1 C14 C2 112.0(3)
C3 C2 C1 119.6(3)
C3 C2 C14 119.1(3)
C1 C2 C14 121.4(3)
C6 C1 C2 119.5(3)
C6 C1 C7 119.5(3)
C2 C1 C7 120.9(3)
C1 C6 C5 120.8(3)
C1 C6 H6 119.6
C5 C6 H6 119.6
C4 C5 C6 119.6(3)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C4 C3 120.3(3)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C3 C2 120.2(3)
C4 C3 H3 119.9
C2 C3 H3 119.9
O1 C7 N1 124.9(3)
O1 C7 C1 120.2(3)
N1 C7 C1 114.9(3)
C9 C8 C13 120.7(3)
C9 C8 N1 122.1(3)
C13 C8 N1 117.2(3)
C12 C13 C8 119.3(3)
C12 C13 H13 120.4
C8 C13 H13 120.4
C11 C12 C13 121.4(3)
C11 C12 H12 119.3
C13 C12 H12 119.3
C10 C11 C12 118.0(3)
C10 C11 H11 121.0
C12 C11 H11 121.0
C11 C10 C9 122.1(3)
C11 C10 Br1 118.6(3)
C9 C10 Br1 119.3(3)
C8 C9 C10 118.5(3)
C8 C9 H9 120.8
C10 C9 H9 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.905(3)
F1 C14 1.347(4)
F2 C14 1.343(5)
F3 C14 1.343(4)
O1 C7 1.223(4)
N1 C7 1.349(5)
N1 C8 1.424(4)
N1 H1 0.90(4)
C14 C2 1.496(5)
C2 C3 1.392(6)
C2 C1 1.400(5)
C1 C6 1.381(5)
C1 C7 1.512(5)
C6 C5 1.390(5)
C6 H6 0.9500
C5 C4 1.382(5)
C5 H5 0.9500
C4 C3 1.383(6)
C4 H4 0.9500
C3 H3 0.9500
C8 C9 1.386(5)
C8 C13 1.387(5)
C13 C12 1.386(5)
C13 H13 0.9500
C12 C11 1.385(5)
C12 H12 0.9500
C11 C10 1.385(6)
C11 H11 0.9500
C10 C9 1.388(5)
C9 H9 0.9500
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
F2 C14 C2 C3 -97.2(4)
F3 C14 C2 C3 141.9(4)
F1 C14 C2 C3 22.9(5)
F2 C14 C2 C1 83.7(4)
F3 C14 C2 C1 -37.3(5)
F1 C14 C2 C1 -156.3(3)
C3 C2 C1 C6 -0.7(5)
C14 C2 C1 C6 178.5(3)
C3 C2 C1 C7 175.0(4)
C14 C2 C1 C7 -5.8(5)
C2 C1 C6 C5 2.2(5)
C7 C1 C6 C5 -173.5(3)
C1 C6 C5 C4 -1.8(5)
C6 C5 C4 C3 -0.1(6)
C5 C4 C3 C2 1.6(7)
C1 C2 C3 C4 -1.2(6)
C14 C2 C3 C4 179.6(4)
C8 N1 C7 O1 9.3(5)
C8 N1 C7 C1 -171.9(3)
C6 C1 C7 O1 109.9(4)
C2 C1 C7 O1 -65.8(5)
C6 C1 C7 N1 -69.0(4)
C2 C1 C7 N1 115.4(3)
C7 N1 C8 C9 -41.3(5)
C7 N1 C8 C13 139.3(3)
C9 C8 C13 C12 1.5(5)
N1 C8 C13 C12 -179.0(3)
C8 C13 C12 C11 0.4(5)
C13 C12 C11 C10 -1.1(5)
C12 C11 C10 C9 -0.1(5)
C12 C11 C10 Br1 179.3(2)
C13 C8 C9 C10 -2.7(5)
N1 C8 C9 C10 177.9(3)
C11 C10 C9 C8 1.9(5)
Br1 C10 C9 C8 -177.4(2)

_cod_database_fobs_code 2108312
