#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/36/2233648.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_2233648
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Shahani, Tara'
'Nayak, Prakash S.'
'Narayana, B.'
'Sarojini, B. K.'
_publ_section_title
;
 N-(4-Bromophenyl)-2-(4-chlorophenyl)acetamide
;
_journal_coeditor_code           TK5050
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o519
_journal_paper_doi               10.1107/S1600536812002383
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H11 Br Cl N O'
_chemical_formula_moiety         'C14 H11 Br Cl N O'
_chemical_formula_sum            'C14 H11 Br Cl N O'
_chemical_formula_weight         324.60
_chemical_name_systematic
;
N-(4-Bromophenyl)-2-(4-chlorophenyl)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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.984(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.584(8)
_cell_length_b                   4.763(3)
_cell_length_c                   18.139(10)
_cell_measurement_reflns_used    1975
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      2.48
_cell_volume                     1336.4(13)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.1229
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12836
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.262
_exptl_absorpt_correction_T_max  0.8258
_exptl_absorpt_correction_T_min  0.2108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.541
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.5271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                1970
_reflns_number_total             3880
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5050.cif
_cod_data_source_block           I
_cod_original_cell_volume        1336.5(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233648
_cod_database_fobs_code          2233648
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 0.28762(3) 0.70007(12) 0.35364(3) 0.0891(3) Uani d . 1 1
O O1 -0.1362(2) 0.6167(5) 0.3893(3) 0.1018(14) Uani d . 1 1
N N1 -0.0827(2) 1.0487(6) 0.37965(19) 0.0562(9) Uani d . 1 1
Cl Cl1 -0.52585(7) 0.1650(2) 0.38444(7) 0.0663(3) Uani d . 1 1
C C1 0.0462(3) 0.7777(7) 0.4237(2) 0.0594(10) Uani d . 1 1
H H1A 0.0171 0.6980 0.4604 0.071 Uiso calc R 1 1
C C2 0.1300(3) 0.7001(8) 0.4179(2) 0.0607(10) Uani d . 1 1
H H2A 0.1574 0.5677 0.4504 0.073 Uiso calc R 1 1
C C3 0.1732(3) 0.8182(8) 0.3642(2) 0.0573(9) Uani d . 1 1
C C4 0.1331(3) 1.0177(8) 0.3172(2) 0.0667(11) Uani d . 1 1
H H4A 0.1627 1.1011 0.2814 0.080 Uiso calc R 1 1
C C5 0.0495(3) 1.0933(8) 0.3232(3) 0.0652(11) Uani d . 1 1
H H5A 0.0226 1.2285 0.2914 0.078 Uiso calc R 1 1
C C6 0.0047(2) 0.9718(6) 0.3758(2) 0.0471(8) Uani d . 1 1
C C7 -0.1479(3) 0.8708(6) 0.3853(2) 0.0597(10) Uani d . 1 1
C C8 -0.2359(3) 1.0010(7) 0.3854(3) 0.0756(14) Uani d . 1 1
H H8A -0.2475 1.1210 0.3421 0.091 Uiso calc R 1 1
H H8B -0.2354 1.1186 0.4291 0.091 Uiso calc R 1 1
C C9 -0.3081(3) 0.7905(7) 0.3849(3) 0.0626(12) Uani d . 1 1
C C10 -0.3510(3) 0.6898(7) 0.3188(3) 0.0634(11) Uani d . 1 1
H H10A -0.3350 0.7532 0.2740 0.076 Uiso calc R 1 1
C C11 -0.4175(3) 0.4957(7) 0.3185(2) 0.0578(9) Uani d . 1 1
H H11A -0.4465 0.4305 0.2739 0.069 Uiso calc R 1 1
C C12 -0.4396(2) 0.4024(7) 0.3850(2) 0.0491(9) Uani d . 1 1
C C13 -0.3986(3) 0.4935(8) 0.4515(2) 0.0577(9) Uani d . 1 1
H H13A -0.4145 0.4264 0.4960 0.069 Uiso calc R 1 1
C C14 -0.3332(3) 0.6879(8) 0.4508(3) 0.0625(11) Uani d . 1 1
H H14A -0.3049 0.7522 0.4957 0.075 Uiso calc R 1 1
H H1N1 -0.087(3) 1.197(8) 0.376(2) 0.058(12) Uiso d . 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'
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'
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
C7 N1 C6 125.6(3)
C7 N1 H1N1 125(4)
C6 N1 H1N1 109(4)
C2 C1 C6 120.7(4)
C2 C1 H1A 119.6
C6 C1 H1A 119.6
C3 C2 C1 119.8(4)
C3 C2 H2A 120.1
C1 C2 H2A 120.1
C2 C3 C4 120.0(4)
C2 C3 Br1 119.9(3)
C4 C3 Br1 120.2(3)
C5 C4 C3 119.8(4)
C5 C4 H4A 120.1
C3 C4 H4A 120.1
C4 C5 C6 120.8(4)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C1 C6 C5 118.8(4)
C1 C6 N1 121.5(3)
C5 C6 N1 119.7(3)
O1 C7 N1 121.5(3)
O1 C7 C8 122.4(3)
N1 C7 C8 116.1(3)
C7 C8 C9 113.9(3)
C7 C8 H8A 108.8
C9 C8 H8A 108.8
C7 C8 H8B 108.8
C9 C8 H8B 108.8
H8A C8 H8B 107.7
C10 C9 C14 117.7(4)
C10 C9 C8 121.2(4)
C14 C9 C8 121.1(4)
C9 C10 C11 121.1(4)
C9 C10 H10A 119.4
C11 C10 H10A 119.4
C12 C11 C10 118.6(4)
C12 C11 H11A 120.7
C10 C11 H11A 120.7
C13 C12 C11 122.4(4)
C13 C12 Cl1 119.1(3)
C11 C12 Cl1 118.6(3)
C12 C13 C14 118.2(4)
C12 C13 H13A 120.9
C14 C13 H13A 120.9
C13 C14 C9 122.0(4)
C13 C14 H14A 119.0
C9 C14 H14A 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.902(4)
O1 C7 1.225(4)
N1 C7 1.337(5)
N1 C6 1.421(5)
N1 H1N1 0.71(4)
Cl1 C12 1.756(4)
C1 C2 1.374(6)
C1 C6 1.374(5)
C1 H1A 0.9300
C2 C3 1.370(6)
C2 H2A 0.9300
C3 C4 1.376(6)
C4 C5 1.369(6)
C4 H4A 0.9300
C5 C6 1.376(5)
C5 H5A 0.9300
C7 C8 1.506(5)
C8 C9 1.506(5)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.384(6)
C9 C14 1.391(6)
C10 C11 1.388(6)
C10 H10A 0.9300
C11 C12 1.369(5)
C11 H11A 0.9300
C12 C13 1.364(5)
C13 C14 1.379(6)
C13 H13A 0.9300
C14 H14A 0.9300
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
_geom_hbond_publ_flag
N1 H1N1 O1 1_565 0.71(4) 2.17(4) 2.843(4) 160(5) 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
C6 C1 C2 C3 0.4(6)
C1 C2 C3 C4 1.2(6)
C1 C2 C3 Br1 -177.5(3)
C2 C3 C4 C5 -1.4(6)
Br1 C3 C4 C5 177.3(3)
C3 C4 C5 C6 -0.1(6)
C2 C1 C6 C5 -1.8(6)
C2 C1 C6 N1 178.2(3)
C4 C5 C6 C1 1.7(6)
C4 C5 C6 N1 -178.4(4)
C7 N1 C6 C1 -46.6(6)
C7 N1 C6 C5 133.5(4)
C6 N1 C7 O1 1.5(7)
C6 N1 C7 C8 -177.6(4)
O1 C7 C8 C9 -4.4(7)
N1 C7 C8 C9 174.7(4)
C7 C8 C9 C10 -89.3(5)
C7 C8 C9 C14 89.9(5)
C14 C9 C10 C11 0.8(5)
C8 C9 C10 C11 180.0(3)
C9 C10 C11 C12 -0.7(5)
C10 C11 C12 C13 0.1(5)
C10 C11 C12 Cl1 178.1(3)
C11 C12 C13 C14 0.4(5)
Cl1 C12 C13 C14 -177.6(3)
C12 C13 C14 C9 -0.3(5)
C10 C9 C14 C13 -0.3(5)
C8 C9 C14 C13 -179.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 741952
