#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/19/2231911.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_2231911
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Quintero, David E.'
'Zuluaga, Fabio'
'Kennedy, Alan R.'
'De Almeida Santos, Regina H.'
_publ_section_title
;
 2-Bromo-N-(4-chlorophenyl)-2-methylpropanamide
;
_journal_coeditor_code           HG5088
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2580
_journal_paper_doi               10.1107/S1600536811035562
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H11 Br Cl N O'
_chemical_formula_moiety         'C10 H11 Br Cl N O'
_chemical_formula_sum            'C10 H11 Br Cl N O'
_chemical_formula_weight         276.56
_chemical_melting_point          386.0(10)
_chemical_name_systematic
;
2-Bromo-N-(4-chlorophenyl)-2-methylpropanamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.7449(3)
_cell_length_b                   10.1063(3)
_cell_length_c                   22.8803(7)
_cell_measurement_reflns_used    4107
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.66
_cell_measurement_theta_min      2.89
_cell_volume                     2253.36(12)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       ω
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9676
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.853
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.3870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.601
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0275P)²+1.8897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                2225
_reflns_number_total             2684
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5088.cif
_cod_data_source_block           I
_cod_database_code               2231911
_cod_database_fobs_code          2231911
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.48117(2) 0.03662(3) 0.143191(11) 0.02744(9) Uani d . 1 1
Cl Cl1 1.31938(6) 0.04546(7) -0.00111(2) 0.02798(15) Uani d . 1 1
O O1 0.77815(16) -0.19000(14) 0.15413(7) 0.0189(3) Uani d . 1 1
N N1 0.81397(19) 0.03082(19) 0.14313(8) 0.0150(4) Uani d . 1 1
C C1 0.5483(3) -0.1697(2) 0.22170(11) 0.0275(6) Uani d . 1 1
H H1A 0.6122 -0.2144 0.2483 0.041 Uiso calc R 1 1
H H1B 0.5265 -0.2286 0.1889 0.041 Uiso calc R 1 1
H H1C 0.4639 -0.1476 0.2428 0.041 Uiso calc R 1 1
C C2 0.6140(2) -0.0437(2) 0.19856(9) 0.0168(5) Uani d . 1 1
C C3 0.7429(2) -0.0750(2) 0.16220(9) 0.0138(4) Uani d . 1 1
C C4 0.6432(3) 0.0534(2) 0.24801(10) 0.0215(5) Uani d . 1 1
H H4A 0.5595 0.0670 0.2710 0.032 Uiso calc R 1 1
H H4B 0.6734 0.1381 0.2316 0.032 Uiso calc R 1 1
H H4C 0.7154 0.0175 0.2733 0.032 Uiso calc R 1 1
C C5 0.9350(2) 0.0288(2) 0.10845(9) 0.0139(4) Uani d . 1 1
C C6 1.0272(2) -0.0771(2) 0.10905(10) 0.0176(5) Uani d . 1 1
H H6 1.0088 -0.1532 0.1321 0.021 Uiso calc R 1 1
C C7 1.1457(2) -0.0702(2) 0.07567(10) 0.0193(5) Uani d . 1 1
H H7 1.2092 -0.1415 0.0761 0.023 Uiso calc R 1 1
C C8 1.1717(2) 0.0402(2) 0.04186(9) 0.0191(5) Uani d . 1 1
C C9 1.0812(2) 0.1457(2) 0.04075(9) 0.0196(5) Uani d . 1 1
H H9 1.0999 0.2211 0.0173 0.024 Uiso calc R 1 1
C C10 0.9626(2) 0.1399(2) 0.07439(10) 0.0172(5) Uani d . 1 1
H H10 0.9000 0.2120 0.0742 0.021 Uiso calc R 1 1
H H1N 0.778(3) 0.103(3) 0.1467(11) 0.024(7) Uiso d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.01641(13) 0.03536(16) 0.03055(14) 0.00118(10) -0.00217(9) 0.00496(12)
Cl1 0.0173(3) 0.0437(4) 0.0230(3) -0.0036(3) 0.0062(2) 0.0048(3)
O1 0.0206(8) 0.0105(7) 0.0256(8) -0.0002(6) 0.0060(6) -0.0013(6)
N1 0.0178(9) 0.0096(9) 0.0176(9) 0.0016(8) 0.0048(7) -0.0001(8)
C1 0.0317(14) 0.0173(12) 0.0335(14) -0.0036(10) 0.0161(11) 0.0016(11)
C2 0.0172(11) 0.0139(11) 0.0194(10) 0.0012(9) 0.0025(9) 0.0004(9)
C3 0.0155(10) 0.0133(10) 0.0125(9) -0.0004(8) -0.0016(8) 0.0008(8)
C4 0.0259(12) 0.0177(11) 0.0210(11) 0.0022(10) 0.0066(9) -0.0044(10)
C5 0.0141(10) 0.0158(10) 0.0117(9) -0.0024(9) -0.0006(8) -0.0027(9)
C6 0.0203(11) 0.0152(10) 0.0171(10) 0.0004(9) 0.0016(9) 0.0022(9)
C7 0.0166(11) 0.0214(12) 0.0199(11) 0.0026(9) 0.0017(9) -0.0019(9)
C8 0.0135(10) 0.0295(13) 0.0142(10) -0.0053(10) 0.0017(8) -0.0013(10)
C9 0.0217(12) 0.0217(12) 0.0155(10) -0.0072(10) -0.0008(9) 0.0036(9)
C10 0.0186(11) 0.0153(11) 0.0178(10) -0.0005(9) -0.0002(9) 0.0008(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N1 C5 126.59(19)
C3 N1 H1N 117.2(19)
C5 N1 H1N 115.3(19)
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
C1 C2 C4 111.06(18)
C1 C2 C3 111.06(18)
C4 C2 C3 112.42(18)
C1 C2 Br1 106.84(16)
C4 C2 Br1 109.42(14)
C3 C2 Br1 105.74(14)
O1 C3 N1 124.1(2)
O1 C3 C2 120.33(19)
N1 C3 C2 115.56(18)
C2 C4 H4A 109.5
C2 C4 H4B 109.5
H4A C4 H4B 109.5
C2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C10 C5 C6 119.9(2)
C10 C5 N1 117.43(19)
C6 C5 N1 122.59(19)
C7 C6 C5 119.4(2)
C7 C6 H6 120.3
C5 C6 H6 120.3
C8 C7 C6 120.1(2)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C9 121.1(2)
C7 C8 Cl1 119.44(18)
C9 C8 Cl1 119.49(18)
C8 C9 C10 119.2(2)
C8 C9 H9 120.4
C10 C9 H9 120.4
C9 C10 C5 120.3(2)
C9 C10 H10 119.9
C5 C10 H10 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.985(2)
Cl1 C8 1.744(2)
O1 C3 1.226(2)
N1 C3 1.346(3)
N1 C5 1.422(3)
N1 H1N 0.81(3)
C1 C2 1.521(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C4 1.524(3)
C2 C3 1.539(3)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C10 1.393(3)
C5 C6 1.397(3)
C6 C7 1.387(3)
C6 H6 0.9500
C7 C8 1.381(3)
C7 H7 0.9500
C8 C9 1.384(3)
C9 C10 1.390(3)
C9 H9 0.9500
C10 H10 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 H1N O1 7_765 0.81(3) 2.17(3) 2.972(2) 169(3)
C10 H10 O1 7_765 0.95 2.71 3.433(3) 133.4
C4 H4B O1 7_765 0.98 2.53 3.453(3) 157.8
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
C5 N1 C3 O1 3.7(3)
C5 N1 C3 C2 -179.28(19)
C1 C2 C3 O1 1.6(3)
C4 C2 C3 O1 126.7(2)
Br1 C2 C3 O1 -113.94(19)
C1 C2 C3 N1 -175.6(2)
C4 C2 C3 N1 -50.5(2)
Br1 C2 C3 N1 68.9(2)
C3 N1 C5 C10 155.0(2)
C3 N1 C5 C6 -27.1(3)
C10 C5 C6 C7 0.1(3)
N1 C5 C6 C7 -177.7(2)
C5 C6 C7 C8 -0.4(3)
C6 C7 C8 C9 0.3(3)
C6 C7 C8 Cl1 -178.54(17)
C7 C8 C9 C10 0.1(3)
Cl1 C8 C9 C10 178.97(17)
C8 C9 C10 C5 -0.4(3)
C6 C5 C10 C9 0.3(3)
N1 C5 C10 C9 178.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25641473
2 PubChem 15567787
