#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/46/2224670.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_2224670
loop_
_publ_author_name
'Nogueira, Thais C. M.'
'de Souza, Marcus V. N.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N-(4-Bromophenyl)-2-(2-thienyl)acetamide
;
_journal_coeditor_code           HG2617
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o177
_journal_paper_doi               10.1107/S1600536809053355
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 Br N O S'
_chemical_formula_moiety         'C12 H10 Br N O S'
_chemical_formula_sum            'C12 H10 Br N O S'
_chemical_formula_weight         296.18
_chemical_name_systematic
;
N-(4-Bromophenyl)-2-(2-thienyl)acetamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.419(2)
_cell_angle_beta                 88.437(2)
_cell_angle_gamma                84.479(2)
_cell_formula_units_Z            2
_cell_length_a                   4.7517(2)
_cell_length_b                   10.7283(3)
_cell_length_c                   11.7964(3)
_cell_measurement_reflns_used    2592
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     581.82(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9757
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            pale-brown
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.98
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.98
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.031
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                1847
_reflns_number_total             2045
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2617.cif
_cod_data_source_block           I
_cod_database_code               2224670
_cod_database_fobs_code          2224670
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
Br Br 0.27885(7) -0.23040(3) 0.97460(3) 0.03386(19) Uani d . 1 . .
O O1 0.0821(5) 0.2338(2) 0.4702(2) 0.0338(6) Uani d . 1 . .
N N1 0.5204(5) 0.1924(3) 0.5506(2) 0.0237(6) Uani d D 1 . .
H H1N 0.696(3) 0.211(3) 0.540(3) 0.028 Uiso d D 1 . .
S S1 0.0537(8) 0.5801(3) 0.3373(3) 0.0278(6) Uani d P 0.660(5) A 1
C C1 0.2232(6) 0.4487(3) 0.3020(3) 0.0249(7) Uani d P 0.660(5) A 1
C C2 -0.1461(8) 0.6162(4) 0.2202(3) 0.0361(8) Uani d P 0.660(5) A 1
H H2 -0.2806 0.6894 0.2040 0.043 Uiso calc PR 0.660(5) A 1
C C3 -0.1056(7) 0.5346(4) 0.1488(3) 0.0318(8) Uani d P 0.660(5) A 1
H H3 -0.2006 0.5420 0.0774 0.038 Uiso calc PR 0.660(5) A 1
C C4 0.108(4) 0.4342(19) 0.2003(15) 0.035(4) Uani d P 0.660(5) A 1
H H4 0.1644 0.3633 0.1668 0.042 Uiso calc PR 0.660(5) A 1
S S1' 0.1360(17) 0.4123(9) 0.1850(6) 0.0245(14) Uani d P 0.340(5) A 2
C C1' 0.2232(6) 0.4487(3) 0.3020(3) 0.0249(7) Uani d P 0.340(5) A 2
C C2' -0.1461(8) 0.6162(4) 0.2202(3) 0.0361(8) Uani d P 0.340(5) A 2
H H2' -0.2772 0.6904 0.2108 0.043 Uiso calc PR 0.340(5) A 2
C C3' -0.1056(7) 0.5346(4) 0.1488(3) 0.0318(8) Uani d P 0.340(5) A 2
H H3' -0.2134 0.5474 0.0797 0.038 Uiso calc PR 0.340(5) A 2
C C4' 0.072(7) 0.561(3) 0.323(3) 0.035(4) Uani d P 0.340(5) A 2
H H4' 0.0977 0.5980 0.3879 0.042 Uiso calc PR 0.340(5) A 2
C C5 0.4454(7) 0.3645(4) 0.3784(3) 0.0351(8) Uani d . 1 . .
H H5A 0.5485 0.4183 0.4176 0.042 Uiso calc R 1 A 1
H H5B 0.5828 0.3256 0.3290 0.042 Uiso calc R 1 A 1
C C6 0.3296(6) 0.2578(3) 0.4702(3) 0.0251(7) Uani d . 1 A .
C C7 0.4675(6) 0.0909(3) 0.6462(3) 0.0227(7) Uani d . 1 . .
C C8 0.2767(7) 0.0013(3) 0.6398(3) 0.0251(7) Uani d . 1 . .
H H8 0.1806 0.0071 0.5689 0.030 Uiso calc R 1 . .
C C9 0.2278(7) -0.0953(3) 0.7360(3) 0.0266(7) Uani d . 1 . .
H H9 0.0995 -0.1566 0.7315 0.032 Uiso calc R 1 . .
C C10 0.3667(7) -0.1026(3) 0.8397(3) 0.0252(7) Uani d . 1 . .
C C11 0.5612(7) -0.0172(3) 0.8476(3) 0.0279(7) Uani d . 1 . .
H H11 0.6607 -0.0254 0.9181 0.033 Uiso calc R 1 . .
C C12 0.6090(7) 0.0808(3) 0.7505(3) 0.0255(7) Uani d . 1 . .
H H12 0.7389 0.1414 0.7553 0.031 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C7 . . 126.1(3) ?
C6 N1 H1n . . 117(2) ?
C7 N1 H1n . . 117(2) ?
C2 S1 C1 . . 93.6(2) ?
C4 C1 C5 . . 129.6(8) ?
C4 C1 S1 . . 108.3(8) ?
C5 C1 S1 . . 122.0(3) ?
C3 C2 S1 . . 115.4(3) ?
C3 C2 H2 . . 122.3 ?
S1 C2 H2 . . 122.3 ?
C2 C3 C4 . . 107.7(7) ?
C2 C3 H3 . . 126.2 ?
C4 C3 H3 . . 126.2 ?
C1 C4 C3 . . 114.9(11) ?
C1 C4 H4 . . 122.6 ?
C3 C4 H4 . . 122.6 ?
C1' S1' C3' . . 94.5(5) ?
C4' C1' C5 . . 126.1(14) ?
C4' C1' S1' . . 114.4(14) ?
C5 C1' S1' . . 119.4(4) ?
C3' C2' C4' . . 105.2(11) ?
C3' C2' H2' . . 127.4 ?
C4' C2' H2' . . 127.4 ?
C2' C3' S1' . . 117.9(4) ?
C2' C3' H3' . . 121.1 ?
S1' C3' H3' . . 121.1 ?
C1' C4' C2' . . 108.0(19) ?
C1' C4' H4' . . 126.0 ?
C2' C4' H4' . . 126.0 ?
C1' C5 C6 . . 113.6(3) ?
C1 C5 C6 . . 113.6(3) ?
C1' C5 H5A . . 108.8 ?
C1 C5 H5A . . 108.8 ?
C6 C5 H5A . . 108.8 ?
C1' C5 H5B . . 108.8 ?
C1 C5 H5B . . 108.8 ?
C6 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.7 ?
O1 C6 N1 . . 123.6(3) ?
O1 C6 C5 . . 122.0(3) ?
N1 C6 C5 . . 114.5(3) ?
C12 C7 C8 . . 119.5(3) ?
C12 C7 N1 . . 118.5(3) ?
C8 C7 N1 . . 122.1(3) ?
C9 C8 C7 . . 120.1(3) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C10 C9 C8 . . 119.7(3) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C11 C10 C9 . . 121.3(3) ?
C11 C10 Br . . 119.6(2) ?
C9 C10 Br . . 119.1(2) ?
C10 C11 C12 . . 118.9(3) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C7 C12 C11 . . 120.4(3) ?
C7 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br C10 . 1.907(3) ?
O1 C6 . 1.228(4) ?
N1 C6 . 1.352(4) ?
N1 C7 . 1.407(4) ?
N1 H1N . 0.875(10) ?
S1 C2 . 1.647(5) ?
S1 C1 . 1.687(4) ?
C1 C4 . 1.381(17) ?
C1 C5 . 1.493(5) ?
C2 C3 . 1.348(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.439(19) ?
C3 H3 . 0.9500 ?
C4 H4 . 0.9500 ?
S1' C1' . 1.594(8) ?
S1' C3' . 1.641(9) ?
C1' C4' . 1.42(3) ?
C1' C5 . 1.493(5) ?
C2' C3' . 1.348(5) ?
C2' C4' . 1.59(3) ?
C2' H2' . 0.9500 ?
C3' H3' . 0.9500 ?
C4' H4' . 0.9500 ?
C5 C6 . 1.514(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C7 C12 . 1.396(4) ?
C7 C8 . 1.399(4) ?
C8 C9 . 1.377(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.388(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.382(5) ?
C11 C12 . 1.391(5) ?
C11 H11 . 0.9500 ?
C12 H12 . 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 1_655 0.875(17) 2.00(2) 2.848(3) 162(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 S1 C1 C4 . . . . -2.5(10) ?
C2 S1 C1 C5 . . . . -179.0(3) ?
C1 S1 C2 C3 . . . . 0.8(4) ?
S1 C2 C3 C4 . . . . 1.0(9) ?
C5 C1 C4 C3 . . . . 179.8(7) ?
S1 C1 C4 C3 . . . . 3.6(17) ?
C2 C3 C4 C1 . . . . -3.0(16) ?
C3' S1' C1' C4' . . . . -0.6(19) ?
C3' S1' C1' C5 . . . . 178.7(3) ?
C4' C2' C3' S1' . . . . 0.1(13) ?
C1' S1' C3' C2' . . . . 0.3(6) ?
C5 C1' C4' C2' . . . . -178.6(8) ?
S1' C1' C4' C2' . . . . 1(3) ?
C3' C2' C4' C1' . . . . 0(2) ?
C4' C1' C5 C6 . . . . 89.3(18) ?
S1' C1' C5 C6 . . . . -89.9(5) ?
C4 C1 C5 C6 . . . . -87.3(12) ?
S1 C1 C5 C6 . . . . 88.4(4) ?
C7 N1 C6 O1 . . . . -1.5(5) ?
C7 N1 C6 C5 . . . . 178.7(3) ?
C1' C5 C6 O1 . . . . 9.4(5) ?
C1 C5 C6 O1 . . . . 9.4(5) ?
C1' C5 C6 N1 . . . . -170.8(3) ?
C1 C5 C6 N1 . . . . -170.8(3) ?
C6 N1 C7 C12 . . . . -144.4(3) ?
C6 N1 C7 C8 . . . . 35.0(5) ?
C12 C7 C8 C9 . . . . 0.5(5) ?
N1 C7 C8 C9 . . . . -178.9(3) ?
C7 C8 C9 C10 . . . . 0.6(5) ?
C8 C9 C10 C11 . . . . -2.2(5) ?
C8 C9 C10 Br . . . . 176.1(2) ?
C9 C10 C11 C12 . . . . 2.6(5) ?
Br C10 C11 C12 . . . . -175.7(2) ?
C8 C7 C12 C11 . . . . 0.0(5) ?
N1 C7 C12 C11 . . . . 179.4(3) ?
C10 C11 C12 C7 . . . . -1.5(5) ?
