#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/75/2237564.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_2237564
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Guild, Curtis J.'
'Yathirajan, H. S.'
'Narayana, B.'
'Samshuddin, S.'
_publ_section_title
;
 N-(4-Bromophenyl)acetamide: a new polymorph
;
_journal_coeditor_code           SU2566
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o461
_journal_paper_doi               10.1107/S1600536813005448
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H8 Br N O'
_chemical_formula_moiety         'C8 H8 Br N O'
_chemical_formula_sum            'C8 H8 Br N O'
_chemical_formula_weight         214.06
_chemical_name_systematic
;
N-(4-Bromophenyl)acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 117.750(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7250(7)
_cell_length_b                   9.3876(11)
_cell_length_c                   14.4434(14)
_cell_measurement_reflns_used    3269
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.2649
_cell_measurement_theta_min      3.4162
_cell_volume                     806.96(15)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur (Eos, Gemini)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10902
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.34
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    5.031
_exptl_absorpt_correction_T_max  0.4646
_exptl_absorpt_correction_T_min  0.2959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction 2010)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.435
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0329P)²+0.1779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                2099
_reflns_number_total             2689
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2566.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237564
_cod_database_fobs_code          2237564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 -0.12616(4) 0.70900(2) 0.493749(17) 0.03329(8) Uani d . 1 1
O O1 0.4333(2) 0.63844(14) 0.19611(11) 0.0286(3) Uani d . 1 1
N N1 0.3872(3) 0.85329(15) 0.25584(12) 0.0212(3) Uani d . 1 1
H H1 0.4358 0.9432 0.2658 0.025 Uiso d R 1 1
C C1 0.5678(4) 0.8449(2) 0.14665(17) 0.0283(4) Uani d . 1 1
H H1A 0.5162 0.8041 0.0767 0.042 Uiso calc R 1 1
H H1B 0.7312 0.8344 0.1869 0.042 Uiso calc R 1 1
H H1C 0.5281 0.9462 0.1404 0.042 Uiso calc R 1 1
C C2 0.4570(3) 0.76819(19) 0.20162(15) 0.0213(4) Uani d . 1 1
C C3 0.2696(3) 0.81333(18) 0.31030(14) 0.0199(3) Uani d . 1 1
C C4 0.2647(3) 0.91062(19) 0.38173(15) 0.0240(4) Uani d . 1 1
H H4 0.3428 0.9985 0.3931 0.029 Uiso calc R 1 1
C C5 0.1473(3) 0.8806(2) 0.43633(16) 0.0265(4) Uani d . 1 1
H H5 0.1435 0.9475 0.4849 0.032 Uiso calc R 1 1
C C6 0.0351(3) 0.7520(2) 0.41948(15) 0.0233(4) Uani d . 1 1
C C7 0.0369(3) 0.6541(2) 0.34821(15) 0.0247(4) Uani d . 1 1
H H7 -0.0407 0.5662 0.3374 0.030 Uiso calc R 1 1
C C8 0.1522(3) 0.68544(19) 0.29313(15) 0.0235(4) Uani d . 1 1
H H8 0.1518 0.6195 0.2431 0.028 Uiso calc R 1 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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C3 127.45(15)
C2 N1 H1 117.0
C3 N1 H1 115.1
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 N1 123.83(17)
O1 C2 C1 121.58(17)
N1 C2 C1 114.59(16)
C4 C3 C8 119.39(18)
C4 C3 N1 117.09(16)
C8 C3 N1 123.46(17)
C5 C4 C3 120.52(17)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 119.17(17)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C7 121.18(18)
C5 C6 Br1 119.76(15)
C7 C6 Br1 119.06(15)
C8 C7 C6 119.33(18)
C8 C7 H7 120.3
C6 C7 H7 120.3
C7 C8 C3 120.39(18)
C7 C8 H8 119.8
C3 C8 H8 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.8906(19)
O1 C2 1.226(2)
N1 C2 1.347(2)
N1 C3 1.401(2)
N1 H1 0.8922
C1 C2 1.501(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C3 C4 1.390(2)
C3 C8 1.394(2)
C4 C5 1.380(3)
C4 H4 0.9500
C5 C6 1.384(3)
C5 H5 0.9500
C6 C7 1.384(3)
C7 C8 1.377(3)
C7 H7 0.9500
C8 H8 0.9500
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
N1 H1 O1 2_655 0.89 2.00 2.885(2) 174
C1 H1B Cg1 1_655 0.98 2.84 3.761(3) 157
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
C3 N1 C2 O1 -3.1(3)
C3 N1 C2 C1 176.68(18)
C2 N1 C3 C4 164.06(18)
C2 N1 C3 C8 -18.6(3)
C8 C3 C4 C5 0.8(3)
N1 C3 C4 C5 178.23(17)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C7 -0.7(3)
C4 C5 C6 Br1 179.88(15)
C5 C6 C7 C8 0.0(3)
Br1 C6 C7 C8 179.37(15)
C6 C7 C8 C3 1.2(3)
C4 C3 C8 C7 -1.6(3)
N1 C3 C8 C7 -178.81(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7399
2 PubChem 7683
