#------------------------------------------------------------------------------
#$Date: 2018-11-17 05:34:44 +0200 (Sat, 17 Nov 2018) $
#$Revision: 212032 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108311.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_2108311
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.227(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8056(2)
_cell_length_b                   27.8678(10)
_cell_length_c                   9.8421(4)
_cell_measurement_reflns_used    5637
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.28
_cell_measurement_theta_min      2.92
_cell_volume                     1314.48(9)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10604
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.200
_exptl_absorpt_coefficient_mu    3.157
_exptl_absorpt_correction_T_max  0.6522
_exptl_absorpt_correction_T_min  0.5123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_description       Plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0327
_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)+(0.0183P)²+2.2721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2227
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5013sup1.cif
_cod_data_source_block           PB24
_cod_database_code               2108311
_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   0.432
_shelx_estimated_absorpt_t_max   0.684
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 0.83208(6) -0.04414(2) 0.58176(3) 0.01617(11) Uani 1 1 d . . . . .
F1A F 0.9662(12) 0.2501(2) 0.5747(10) 0.0374(14) Uani 0.77(2) 1 d . . P A 1
F2A F 0.5425(12) 0.2683(2) 0.5312(11) 0.0495(18) Uani 0.77(2) 1 d . . P A 1
F3A F 0.692(3) 0.2809(2) 0.7353(8) 0.081(3) Uani 0.77(2) 1 d . . P A 1
F1B F 0.960(5) 0.2533(8) 0.624(2) 0.0374(14) Uani 0.23(2) 1 d . . P A 2
F2B F 0.560(5) 0.2732(9) 0.586(3) 0.0495(18) Uani 0.23(2) 1 d . . P A 2
F3B F 0.852(4) 0.2701(6) 0.7548(14) 0.034(4) Uani 0.23(2) 1 d . . P A 2
O1 O 0.1090(4) 0.05494(7) 0.8079(2) 0.0179(4) Uani 1 1 d . . . . .
N1 N 0.5344(5) 0.02318(8) 0.7721(2) 0.0112(5) Uani 1 1 d D . . . .
H1 H 0.705(4) 0.0308(12) 0.761(3) 0.024(9) Uiso 1 1 d D . . . .
C11 C 0.3640(6) -0.12293(10) 0.8386(3) 0.0196(6) Uani 1 1 d . . . . .
H11 H 0.326432 -0.155879 0.853930 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5409(6) -0.10978(10) 0.7397(3) 0.0179(6) Uani 1 1 d . . . . .
H10 H 0.624302 -0.133496 0.686532 0.021 Uiso 1 1 calc R U . . .
C9 C 0.5939(6) -0.06162(10) 0.7198(3) 0.0130(6) Uani 1 1 d . . . . .
C8 C 0.4735(5) -0.02570(10) 0.7950(3) 0.0110(5) Uani 1 1 d . . . . .
C7 C 0.3511(6) 0.05959(10) 0.7770(3) 0.0111(5) Uani 1 1 d . . . . .
C1 C 0.4577(6) 0.10824(10) 0.7405(3) 0.0122(6) Uani 1 1 d . . . . .
C2 C 0.6445(6) 0.11450(10) 0.6402(3) 0.0159(6) Uani 1 1 d . . . . .
H2 H 0.713059 0.087347 0.594779 0.019 Uiso 1 1 calc R U . . .
C3 C 0.7305(6) 0.16003(11) 0.6065(3) 0.0211(7) Uani 1 1 d . . . . .
H3 H 0.857565 0.164231 0.537888 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6301(6) 0.19963(10) 0.6735(3) 0.0213(7) Uani 1 1 d . . . . .
C14 C 0.7186(8) 0.24914(12) 0.6366(4) 0.0352(9) Uani 1 1 d . . . . .
C6 C 0.3576(6) 0.14825(10) 0.8057(3) 0.0186(6) Uani 1 1 d . . . . .
H6 H 0.227526 0.144240 0.873004 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4454(7) 0.19375(11) 0.7736(3) 0.0213(7) Uani 1 1 d . . . . .
H5 H 0.379338 0.220880 0.820056 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2418(6) -0.08793(11) 0.9149(3) 0.0178(6) Uani 1 1 d . . . . .
H12 H 0.119418 -0.097037 0.981943 0.021 Uiso 1 1 calc R U . . .
C13 C 0.2971(6) -0.03981(10) 0.8942(3) 0.0155(6) Uani 1 1 d . . . . .
H13 H 0.214283 -0.016200 0.947928 0.019 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
C14 F1B F3B 62.4(15)
C14 F3B F1B 47.8(10)
C7 N1 C8 125.2(2)
C7 N1 H1 117(2)
C8 N1 H1 118(2)
C10 C11 C12 120.0(3)
C10 C11 H11 120.0
C12 C11 H11 120.0
C9 C10 C11 119.0(3)
C9 C10 H10 120.5
C11 C10 H10 120.5
C10 C9 C8 122.2(3)
C10 C9 Br1 118.4(2)
C8 C9 Br1 119.3(2)
C9 C8 C13 117.8(3)
C9 C8 N1 120.5(2)
C13 C8 N1 121.7(2)
O1 C7 N1 124.2(3)
O1 C7 C1 120.0(2)
N1 C7 C1 115.8(2)
C6 C1 C2 119.3(3)
C6 C1 C7 118.5(2)
C2 C1 C7 122.1(2)
C3 C2 C1 120.3(3)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.6(3)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 120.5(3)
C5 C4 C14 119.4(3)
C3 C4 C14 120.1(3)
F2B C14 F1B 123.1(16)
F3A C14 F1A 116.4(9)
F3A C14 F2A 101.7(5)
F1A C14 F2A 99.2(6)
F2B C14 F3B 112.1(13)
F1B C14 F3B 69.8(18)
F2B C14 C4 118.0(13)
F1B C14 C4 114.5(11)
F3A C14 C4 113.1(3)
F1A C14 C4 113.3(4)
F2A C14 C4 111.4(4)
F3B C14 C4 107.5(6)
C5 C6 C1 120.6(3)
C5 C6 H6 119.7
C1 C6 H6 119.7
C6 C5 C4 119.6(3)
C6 C5 H5 120.2
C4 C5 H5 120.2
C13 C12 C11 120.5(3)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C8 120.6(3)
C12 C13 H13 119.7
C8 C13 H13 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.904(3)
F1A C14 1.377(8)
F2A C14 1.395(10)
F3A C14 1.328(6)
F1B C14 1.18(2)
F1B F3B 1.50(3)
F2B C14 1.11(2)
F3B C14 1.413(14)
O1 C7 1.230(3)
N1 C7 1.347(4)
N1 C8 1.415(4)
N1 H1 0.861(18)
C11 C10 1.388(4)
C11 C12 1.388(4)
C11 H11 0.9500
C10 C9 1.383(4)
C10 H10 0.9500
C9 C8 1.395(4)
C8 C13 1.396(4)
C7 C1 1.503(4)
C1 C6 1.390(4)
C1 C2 1.393(4)
C2 C3 1.383(4)
C2 H2 0.9500
C3 C4 1.390(4)
C3 H3 0.9500
C4 C5 1.384(4)
C4 C14 1.496(4)
C6 C5 1.380(4)
C6 H6 0.9500
C5 H5 0.9500
C12 C13 1.385(4)
C12 H12 0.9500
C13 H13 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
C12 C11 C10 C9 0.5(5)
C11 C10 C9 C8 -0.6(5)
C11 C10 C9 Br1 -178.9(2)
C10 C9 C8 C13 0.9(4)
Br1 C9 C8 C13 179.2(2)
C10 C9 C8 N1 179.6(3)
Br1 C9 C8 N1 -2.0(4)
C7 N1 C8 C9 143.4(3)
C7 N1 C8 C13 -37.9(4)
C8 N1 C7 O1 3.2(4)
C8 N1 C7 C1 -176.3(2)
O1 C7 C1 C6 33.6(4)
N1 C7 C1 C6 -146.9(3)
O1 C7 C1 C2 -143.9(3)
N1 C7 C1 C2 35.6(4)
C6 C1 C2 C3 0.4(4)
C7 C1 C2 C3 177.9(3)
C1 C2 C3 C4 0.2(5)
C2 C3 C4 C5 0.1(5)
C2 C3 C4 C14 -179.2(3)
F3B F1B C14 F2B 104(2)
F3B F1B C14 C4 -100.6(12)
F1B F3B C14 F2B -118.5(17)
F1B F3B C14 C4 110.3(12)
C5 C4 C14 F2B -67.3(17)
C3 C4 C14 F2B 112.0(17)
C5 C4 C14 F1B 135.8(14)
C3 C4 C14 F1B -44.9(14)
C5 C4 C14 F3A 23.1(9)
C3 C4 C14 F3A -157.6(9)
C5 C4 C14 F1A 158.4(5)
C3 C4 C14 F1A -22.3(6)
C5 C4 C14 F2A -90.7(6)
C3 C4 C14 F2A 88.6(6)
C5 C4 C14 F3B 60.6(10)
C3 C4 C14 F3B -120.2(10)
C2 C1 C6 C5 -1.2(5)
C7 C1 C6 C5 -178.7(3)
C1 C6 C5 C4 1.4(5)
C3 C4 C5 C6 -0.9(5)
C14 C4 C5 C6 178.4(3)
C10 C11 C12 C13 -0.6(4)
C11 C12 C13 C8 0.8(4)
C9 C8 C13 C12 -1.0(4)
N1 C8 C13 C12 -179.7(3)

_cod_database_fobs_code 2108311
