#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/51/2235195.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_2235195
loop_
_publ_author_name
'Qian, Xiangjun'
'Fang, Zheng'
'Bao, Shuxin'
'Guo, Kai'
'Wei, Ping'
_publ_section_title
;
 2,2-Dibromo-N-(4-fluorophenyl)acetamide
;
_journal_coeditor_code           PV2533
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1824
_journal_paper_doi               10.1107/S1600536812021174
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H6 Br2 F N O'
_chemical_formula_moiety         'C8 H6 Br2 F N O'
_chemical_formula_sum            'C8 H6 Br2 F N O'
_chemical_formula_weight         310.96
_chemical_name_systematic
;
2,2-Dibromo-N-(4-fluorophenyl)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                 96.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.746(2)
_cell_length_b                   10.980(2)
_cell_length_c                   9.426(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1002.5(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonious CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1937
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    8.059
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.498
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0576
_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)+(0.0240P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                900
_reflns_number_total             1827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2533.cif
_cod_data_source_block           I
_cod_original_cell_volume        1002.5(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235195
_cod_database_fobs_code          2235195
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
F F 0.4558(5) 0.2056(4) 0.4060(6) 0.0868(17) Uani d . 1 1
Br Br1 0.27410(10) 0.98435(8) 0.42192(10) 0.0675(3) Uani d . 1 1
Br Br2 -0.02715(10) 0.90635(10) 0.29891(11) 0.0840(4) Uani d . 1 1
O O 0.2133(6) 0.7340(5) 0.2350(5) 0.0635(17) Uani d . 1 1
N N 0.2193(6) 0.6579(5) 0.4588(6) 0.0439(17) Uani d . 1 1
H H0A 0.1995 0.6743 0.5434 0.053 Uiso calc R 1 1
C C1 0.1342(8) 0.8605(6) 0.4178(8) 0.048(2) Uani d . 1 1
H H1A 0.1111 0.8455 0.5149 0.058 Uiso calc R 1 1
C C2 0.1936(8) 0.7438(7) 0.3585(8) 0.046(2) Uani d . 1 1
C C3 0.2775(8) 0.5405(6) 0.4353(8) 0.0390(19) Uani d . 1 1
C C4 0.2452(8) 0.4467(7) 0.5254(8) 0.052(2) Uani d . 1 1
H H4A 0.1850 0.4610 0.5936 0.062 Uiso calc R 1 1
C C5 0.3007(9) 0.3355(8) 0.5140(9) 0.059(3) Uani d . 1 1
H H5A 0.2770 0.2713 0.5708 0.070 Uiso calc R 1 1
C C6 0.3943(8) 0.3195(8) 0.4150(10) 0.054(2) Uani d . 1 1
C C7 0.4260(8) 0.4084(8) 0.3246(8) 0.056(2) Uani d . 1 1
H H7A 0.4856 0.3933 0.2561 0.067 Uiso calc R 1 1
C C8 0.3694(8) 0.5186(7) 0.3364(7) 0.046(2) Uani d . 1 1
H H8A 0.3923 0.5815 0.2771 0.055 Uiso calc R 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
F 0.081(4) 0.047(3) 0.135(5) 0.008(3) 0.025(3) -0.004(3)
Br1 0.0902(7) 0.0504(6) 0.0640(6) -0.0033(6) 0.0179(5) -0.0068(5)
Br2 0.0681(7) 0.1079(10) 0.0749(8) 0.0201(7) 0.0034(5) 0.0095(7)
O 0.116(5) 0.052(4) 0.026(3) 0.013(4) 0.020(3) -0.002(3)
N 0.067(5) 0.037(4) 0.030(4) -0.005(4) 0.016(3) -0.003(3)
C1 0.075(6) 0.037(5) 0.035(5) -0.001(4) 0.017(4) 0.007(4)
C2 0.063(6) 0.046(5) 0.029(5) 0.001(5) -0.002(4) -0.007(5)
C3 0.050(5) 0.036(5) 0.028(5) -0.006(4) -0.010(4) -0.001(4)
C4 0.079(7) 0.042(6) 0.036(5) -0.004(5) 0.009(5) 0.004(4)
C5 0.063(6) 0.039(6) 0.075(7) -0.014(5) 0.012(5) 0.014(5)
C6 0.043(5) 0.040(6) 0.078(7) 0.004(5) 0.007(5) -0.004(5)
C7 0.064(6) 0.054(6) 0.051(6) -0.005(5) 0.014(5) -0.011(5)
C8 0.056(5) 0.044(5) 0.037(5) 0.000(5) 0.009(4) 0.010(4)
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
C2 N C3 124.8(6)
C2 N H0A 117.6
C3 N H0A 117.6
C2 C1 Br2 109.1(5)
C2 C1 Br1 107.6(5)
Br2 C1 Br1 111.3(3)
C2 C1 H1A 109.6
Br2 C1 H1A 109.6
Br1 C1 H1A 109.6
O C2 N 125.6(8)
O C2 C1 122.2(7)
N C2 C1 112.3(6)
C8 C3 C4 119.3(7)
C8 C3 N 123.7(7)
C4 C3 N 116.8(7)
C5 C4 C3 120.2(8)
C5 C4 H4A 119.9
C3 C4 H4A 119.9
C4 C5 C6 118.0(8)
C4 C5 H5A 121.0
C6 C5 H5A 121.0
C7 C6 C5 123.1(8)
C7 C6 F 118.6(8)
C5 C6 F 118.3(8)
C8 C7 C6 118.3(8)
C8 C7 H7A 120.8
C6 C7 H7A 120.8
C7 C8 C3 121.0(7)
C7 C8 H8A 119.5
C3 C8 H8A 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C6 1.394(8)
Br1 C1 1.923(7)
Br2 C1 1.896(7)
O C2 1.205(7)
N C2 1.339(8)
N C3 1.436(8)
N H0A 0.8600
C1 C2 1.536(10)
C1 H1A 0.9800
C3 C8 1.384(9)
C3 C4 1.392(9)
C4 C5 1.344(9)
C4 H4A 0.9300
C5 C6 1.386(10)
C5 H5A 0.9300
C6 C7 1.354(10)
C7 C8 1.340(9)
C7 H7A 0.9300
C8 H8A 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
N H0A O 4_576 0.86 2.06 2.868(7) 156 yes
C1 H1A O 4_576 0.98 2.37 3.178(9) 140 yes
C8 H8A O . 0.93 2.42 2.916(9) 113 no
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 N C2 O 1.4(13)
C3 N C2 C1 -178.8(6)
Br2 C1 C2 O 50.2(9)
Br1 C1 C2 O -70.7(9)
Br2 C1 C2 N -129.7(6)
Br1 C1 C2 N 109.4(6)
C2 N C3 C8 30.9(11)
C2 N C3 C4 -153.6(7)
C8 C3 C4 C5 -1.4(12)
N C3 C4 C5 -177.0(7)
C3 C4 C5 C6 2.7(13)
C4 C5 C6 C7 -3.8(14)
C4 C5 C6 F 177.9(7)
C5 C6 C7 C8 3.4(13)
F C6 C7 C8 -178.3(7)
C6 C7 C8 C3 -2.0(12)
C4 C3 C8 C7 1.0(11)
N C3 C8 C7 176.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657808
