#------------------------------------------------------------------------------
#$Date: 2015-08-22 06:55:39 +0300 (Sat, 22 Aug 2015) $
#$Revision: 153592 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/10/2241031.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_2241031
loop_
_publ_author_name
'Sreenivasa, S.'
'Naveen, S.'
'Lokanath, N. K.'
'Supriya, G. M.'
'Lakshmikantha, H. N.'
'Suchetan, P. A.'
_publ_section_title
;
 Crystal structures of three N-aryl-2,2,2-tribromoacetamides
;
_journal_coeditor_code           HB7472
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1048
_journal_page_last               1053
_journal_paper_doi               10.1107/S2056989015015248
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C9 H5 Br3 F3 N O'
_chemical_formula_moiety         'C9 H5 Br3 F3 N O'
_chemical_formula_sum            'C9 H5 Br3 F3 N O'
_chemical_formula_weight         439.87
_chemical_melting_point          425
_chemical_name_systematic
;
2,2,2-Tribromo-N-[3-(trifluoromethyl)phenyl]acetamide
;
_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                   11.3441(6)
_cell_length_b                   10.3047(6)
_cell_length_c                   20.6397(11)
_cell_measurement_reflns_used    145
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.51
_cell_measurement_theta_min      5.80
_cell_volume                     2412.7(2)
_computing_cell_refinement
;
APEX2 and SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11524
_diffrn_reflns_theta_full        64.51
_diffrn_reflns_theta_max         64.51
_diffrn_reflns_theta_min         5.80
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  5
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    12.661
_exptl_absorpt_correction_T_max  0.1440
_exptl_absorpt_correction_T_min  0.1155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.806
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0395
_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)+(0.0569P)²+5.8187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1967
_reflns_number_total             1978
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            hb7472sup1.cif
_cod_data_source_block           II
_cod_database_code               2241031
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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 0.82269(4) 0.22572(4) 0.72340(2) 0.01621(19) Uani d . 1 1
Br Br2 0.97513(4) 0.19720(5) 0.85195(2) 0.0197(2) Uani d . 1 1
Br Br3 0.93377(4) -0.04340(4) 0.76175(2) 0.0208(2) Uani d . 1 1
F F1 0.2435(3) -0.0016(4) 0.89656(15) 0.0418(9) Uani d . 1 1
F F2 0.3744(3) -0.1282(3) 0.93617(17) 0.0340(8) Uani d . 1 1
F F3 0.2658(2) -0.0138(3) 0.99878(14) 0.0237(6) Uani d . 1 1
N N1 0.6923(3) 0.1851(4) 0.85629(17) 0.0120(8) Uani d . 1 1
H H1 0.7205 0.2589 0.8445 0.014 Uiso calc R 1 1
O O2 0.7243(3) -0.0319(3) 0.84716(15) 0.0149(7) Uani d . 1 1
C C4 0.3873(4) 0.2127(4) 0.9709(2) 0.0172(10) Uani d . 1 1
H H4 0.3194 0.2210 0.9959 0.021 Uiso calc R 1 1
C C3 0.4123(4) 0.0974(4) 0.9396(2) 0.0131(9) Uani d . 1 1
C C2 0.5142(4) 0.0835(4) 0.9018(2) 0.0118(8) Uani d . 1 1
H H2 0.5306 0.0054 0.8811 0.014 Uiso calc R 1 1
C C1 0.5903(4) 0.1887(4) 0.8958(2) 0.0113(8) Uani d . 1 1
C C7 0.7500(4) 0.0795(4) 0.83513(19) 0.0102(8) Uani d . 1 1
C C8 0.8624(4) 0.1125(4) 0.7951(2) 0.0120(8) Uani d . 1 1
C C9 0.3251(4) -0.0103(5) 0.9422(2) 0.0160(9) Uani d . 1 1
C C5 0.4656(4) 0.3166(5) 0.9645(2) 0.0169(9) Uani d . 1 1
H H5 0.4501 0.3945 0.9856 0.020 Uiso calc R 1 1
C C6 0.5654(4) 0.3043(4) 0.9272(2) 0.0150(9) Uani d . 1 1
H H6 0.6167 0.3742 0.9231 0.018 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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 C1 127.3(4)
C7 N1 H1 116.3
C1 N1 H1 116.3
C3 C4 C5 118.9(4)
C3 C4 H4 120.5
C5 C4 H4 120.5
C4 C3 C2 121.2(4)
C4 C3 C9 119.2(4)
C2 C3 C9 119.5(4)
C1 C2 C3 118.8(4)
C1 C2 H2 120.6
C3 C2 H2 120.6
C6 C1 C2 120.1(4)
C6 C1 N1 117.3(4)
C2 C1 N1 122.6(4)
O2 C7 N1 125.8(4)
O2 C7 C8 120.8(4)
N1 C7 C8 113.3(4)
C7 C8 Br3 110.6(3)
C7 C8 Br1 110.2(3)
Br3 C8 Br1 109.1(2)
C7 C8 Br2 108.5(3)
Br3 C8 Br2 108.3(2)
Br1 C8 Br2 110.1(2)
F1 C9 F2 106.6(4)
F1 C9 F3 105.6(3)
F2 C9 F3 105.3(4)
F1 C9 C3 112.8(4)
F2 C9 C3 113.2(4)
F3 C9 C3 112.5(4)
C6 C5 C4 120.4(4)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.6(4)
C5 C6 H6 119.7
C1 C6 H6 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.938(4)
Br2 C8 1.943(4)
Br3 C8 1.926(4)
F1 C9 1.324(5)
F2 C9 1.343(6)
F3 C9 1.348(5)
N1 C7 1.343(6)
N1 C1 1.416(6)
N1 H1 0.8600
O2 C7 1.211(5)
C4 C3 1.383(7)
C4 C5 1.397(7)
C4 H4 0.9300
C3 C2 1.402(6)
C3 C9 1.488(7)
C2 C1 1.391(6)
C2 H2 0.9300
C1 C6 1.386(6)
C7 C8 1.557(6)
C5 C6 1.376(7)
C5 H5 0.9300
C6 H6 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
N1 H1 Br1 . 0.86 2.78 3.144(4) 108
C2 H2 O2 . 0.93 2.34 2.893(6) 118
N1 H1 O2 6_765 0.86 2.24 3.072(5) 161
C6 H6 O2 6_765 0.93 2.58 3.357(5) 142
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 C4 C3 C2 -0.1(7)
C5 C4 C3 C9 -175.5(4)
C4 C3 C2 C1 -0.4(6)
C9 C3 C2 C1 175.1(4)
C3 C2 C1 C6 0.5(6)
C3 C2 C1 N1 -177.1(4)
C7 N1 C1 C6 161.6(4)
C7 N1 C1 C2 -20.8(7)
C1 N1 C7 O2 -0.8(7)
C1 N1 C7 C8 -177.3(4)
O2 C7 C8 Br3 7.2(5)
N1 C7 C8 Br3 -176.1(3)
O2 C7 C8 Br1 127.9(4)
N1 C7 C8 Br1 -55.4(4)
O2 C7 C8 Br2 -111.5(4)
N1 C7 C8 Br2 65.2(4)
C4 C3 C9 F1 85.9(5)
C2 C3 C9 F1 -89.7(5)
C4 C3 C9 F2 -152.9(4)
C2 C3 C9 F2 31.6(6)
C4 C3 C9 F3 -33.6(6)
C2 C3 C9 F3 150.9(4)
C3 C4 C5 C6 0.5(7)
C4 C5 C6 C1 -0.4(7)
C2 C1 C6 C5 -0.1(7)
N1 C1 C6 C5 177.6(4)

_cod_database_fobs_code 2241031
