#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/09/2220946.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_2220946
loop_
_publ_author_name
'Huang, Hui-Ming'
'Luo, Shi-Yuan'
'Li, Shao-Hua'
'Liu, Cheng-Mei'
'Tu, Guo-Gang'
_publ_section_title
;
 2-Benzoylamino-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]ethanamide
;
_journal_coeditor_code           WN2304
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o325
_journal_paper_doi               10.1107/S160053680900124X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H13 Br N4 O2 S'
_chemical_formula_moiety         'C17 H13 Br N4 O2 S'
_chemical_formula_sum            'C17 H13 Br N4 O2 S'
_chemical_formula_weight         417.28
_chemical_name_systematic
;
2-Benzoylamino-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]ethanamide
;
_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                113.334(17)
_cell_angle_beta                 94.018(19)
_cell_angle_gamma                92.78(2)
_cell_formula_units_Z            2
_cell_length_a                   4.020(4)
_cell_length_b                   13.706(9)
_cell_length_c                   16.210(5)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      2.57
_cell_volume                     815.2(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'APEX2 (Bruker, 2004)'
_computing_publication_material
'APEX2 (Bruker, 2004) and publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Bruker X8 APEXII'
_diffrn_measurement_method       'φ and 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  0.0822
_diffrn_reflns_av_sigmaI/netI    0.1676
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4633
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.669
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420.0
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.668
_refine_diff_density_min         -1.395
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.814
_refine_ls_R_factor_all          0.1664
_refine_ls_R_factor_gt           0.1093
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1951P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2622
_refine_ls_wR_factor_ref         0.2812
_reflns_number_gt                1097
_reflns_number_total             2592
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2304.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220946
_cod_database_fobs_code          2220946
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 Br1 0.19570(14) 0.16142(4) 0.64242(3) 0.07526(19) Uani d . 1 . .
S S1 0.3284(3) 0.41677(8) 0.33059(7) 0.0550(4) Uani d . 1 . .
O O1 0.2257(8) 0.6333(2) -0.00717(17) 0.0636(9) Uani d U 1 . .
O O2 0.2253(9) 0.5689(2) 0.25867(18) 0.0687(8) Uani d U 1 . .
N N1 0.2711(9) 0.6635(2) 0.1388(2) 0.0551(12) Uani d . 1 . .
H H1A 0.2352 0.7034 0.1931 0.066 Uiso calc R 1 . .
N N3 0.5949(10) 0.2787(3) 0.1998(2) 0.0621(13) Uani d . 1 . .
N N4 0.5645(10) 0.2351(2) 0.2632(2) 0.0597(8) Uani d U 1 . .
N N2 0.4834(9) 0.4276(2) 0.1728(2) 0.0539(8) Uani d U 1 . .
H H2A 0.5726 0.3992 0.1229 0.065 Uiso calc R 1 . .
C C4 -0.2078(13) 0.9136(3) 0.0368(3) 0.0711(18) Uani d . 1 . .
H H4B -0.3108 0.9254 -0.0112 0.085 Uiso calc R 1 . .
C C5 -0.0907(12) 0.8176(3) 0.0241(3) 0.0610(16) Uani d . 1 . .
H H5A -0.1231 0.7628 -0.0332 0.073 Uiso calc R 1 . .
C C10 0.4756(11) 0.3703(3) 0.2263(3) 0.0512(11) Uani d U 1 . .
C C16 0.1797(12) 0.3039(3) 0.5556(3) 0.0632(17) Uani d . 1 . .
H H16A 0.0838 0.3486 0.6061 0.076 Uiso calc R 1 . .
C C15 0.2691(13) 0.2067(3) 0.5481(3) 0.0603(10) Uani d U 1 . .
C C12 0.3711(10) 0.2674(3) 0.4098(2) 0.0471(9) Uani d U 1 . .
C C14 0.4058(11) 0.1370(3) 0.4729(3) 0.0598(11) Uani d U 1 . .
H H14A 0.4596 0.0701 0.4688 0.072 Uiso calc R 1 . .
C C17 0.2354(12) 0.3345(3) 0.4857(3) 0.0587(11) Uani d U 1 . .
H H17A 0.1807 0.4014 0.4900 0.070 Uiso calc R 1 . .
C C8 0.4114(12) 0.5638(3) 0.1200(3) 0.0560(15) Uani d . 1 . .
H H8A 0.6486 0.5723 0.1144 0.067 Uiso calc R 1 . .
H H8B 0.3068 0.5116 0.0627 0.067 Uiso calc R 1 . .
C C9 0.3647(11) 0.5237(3) 0.1913(2) 0.0475(10) Uani d U 1 . .
C C11 0.4297(11) 0.2963(3) 0.3341(2) 0.0483(10) Uani d U 1 . .
C C13 0.4598(12) 0.1698(3) 0.4041(3) 0.0601(16) Uani d . 1 . .
H H13A 0.5571 0.1253 0.3537 0.072 Uiso calc R 1 . .
C C7 0.1970(11) 0.6938(3) 0.0722(3) 0.0521(13) Uani d U 1 . .
C C6 0.0730(11) 0.7991(3) 0.0926(2) 0.0489(14) Uani d . 1 . .
C C2 -0.0154(12) 0.9776(3) 0.1919(3) 0.0601(16) Uani d . 1 . .
H H2B 0.0074 1.0320 0.2494 0.072 Uiso calc R 1 . .
C C3 -0.1698(12) 0.9930(3) 0.1230(3) 0.0643(17) Uani d . 1 . .
H H3B -0.2533 1.0585 0.1332 0.077 Uiso calc R 1 . .
C C1 0.1113(12) 0.8805(3) 0.1780(3) 0.0555(15) Uani d . 1 . .
H H1B 0.2216 0.8701 0.2259 0.067 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 0.0033 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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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
C10 S1 C11 . . 86.0(2) ?
C7 N1 C8 . . 119.6(3) ?
C7 N1 H1A . . 120.2 ?
C8 N1 H1A . . 120.2 ?
C10 N3 N4 . . 110.7(4) ?
C11 N4 N3 . . 113.3(3) ?
C9 N2 C10 . . 126.3(3) ?
C9 N2 H2A . . 116.8 ?
C10 N2 H2A . . 116.8 ?
C5 C4 C3 . . 118.3(5) ?
C5 C4 H4B . . 120.9 ?
C3 C4 H4B . . 120.9 ?
C4 C5 C6 . . 122.2(4) ?
C4 C5 H5A . . 118.9 ?
C6 C5 H5A . . 118.9 ?
N3 C10 N2 . . 119.8(4) ?
N3 C10 S1 . . 116.5(4) ?
N2 C10 S1 . . 123.6(3) ?
C15 C16 C17 . . 118.0(4) ?
C15 C16 H16A . . 121.0 ?
C17 C16 H16A . . 121.0 ?
C16 C15 C14 . . 122.6(5) ?
C16 C15 Br1 . . 119.4(3) ?
C14 C15 Br1 . . 118.0(4) ?
C13 C12 C17 . . 119.7(4) ?
C13 C12 C11 . . 117.6(3) ?
C17 C12 C11 . . 122.6(4) ?
C13 C14 C15 . . 118.2(4) ?
C13 C14 H14A . . 120.9 ?
C15 C14 H14A . . 120.9 ?
C12 C17 C16 . . 121.0(4) ?
C12 C17 H17A . . 119.5 ?
C16 C17 H17A . . 119.5 ?
N1 C8 C9 . . 112.3(3) ?
N1 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
N1 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.9 ?
O2 C9 N2 . . 121.9(4) ?
O2 C9 C8 . . 125.0(4) ?
N2 C9 C8 . . 113.1(3) ?
N4 C11 C12 . . 123.3(4) ?
N4 C11 S1 . . 113.4(3) ?
C12 C11 S1 . . 123.3(3) ?
C12 C13 C14 . . 120.4(4) ?
C12 C13 H13A . . 119.8 ?
C14 C13 H13A . . 119.8 ?
O1 C7 N1 . . 120.5(4) ?
O1 C7 C6 . . 120.0(4) ?
N1 C7 C6 . . 119.4(3) ?
C5 C6 C1 . . 118.3(4) ?
C5 C6 C7 . . 118.5(3) ?
C1 C6 C7 . . 123.2(4) ?
C3 C2 C1 . . 120.2(4) ?
C3 C2 H2B . . 119.9 ?
C1 C2 H2B . . 119.9 ?
C2 C3 C4 . . 121.2(4) ?
C2 C3 H3B . . 119.4 ?
C4 C3 H3B . . 119.4 ?
C6 C1 C2 . . 119.8(4) ?
C6 C1 H1B . . 120.1 ?
C2 C1 H1B . . 120.1 ?
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
Br1 C15 . 1.898(5) ?
S1 C10 . 1.714(4) ?
S1 C11 . 1.741(5) ?
O1 C7 . 1.242(4) ?
O2 C9 . 1.214(5) ?
N1 C7 . 1.323(6) ?
N1 C8 . 1.430(5) ?
N1 H1A . 0.8600 ?
N3 C10 . 1.285(5) ?
N3 N4 . 1.387(6) ?
N4 C11 . 1.299(5) ?
N2 C9 . 1.349(5) ?
N2 C10 . 1.381(6) ?
N2 H2A . 0.8600 ?
C4 C5 . 1.361(7) ?
C4 C3 . 1.382(6) ?
C4 H4B . 0.9300 ?
C5 C6 . 1.367(7) ?
C5 H5A . 0.9300 ?
C16 C15 . 1.359(7) ?
C16 C17 . 1.382(7) ?
C16 H16A . 0.9300 ?
C15 C14 . 1.387(6) ?
C12 C13 . 1.370(6) ?
C12 C17 . 1.380(5) ?
C12 C11 . 1.461(6) ?
C14 C13 . 1.383(7) ?
C14 H14A . 0.9300 ?
C17 H17A . 0.9300 ?
C8 C9 . 1.483(7) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C13 H13A . 0.9300 ?
C7 C6 . 1.469(6) ?
C6 C1 . 1.383(5) ?
C2 C3 . 1.335(7) ?
C2 C1 . 1.388(6) ?
C2 H2B . 0.9300 ?
C3 H3B . 0.9300 ?
C1 H1B . 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
C16 H16A O2 2_566 0.93 2.49 3.400(5) 167.6
N2 H2A O1 2_665 0.86 1.99 2.835(5) 166.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N3 N4 C11 . . . . -1.0(5) ?
C3 C4 C5 C6 . . . . -2.5(8) ?
N4 N3 C10 N2 . . . . 179.7(4) ?
N4 N3 C10 S1 . . . . 2.2(5) ?
C9 N2 C10 N3 . . . . 179.2(4) ?
C9 N2 C10 S1 . . . . -3.6(6) ?
C11 S1 C10 N3 . . . . -2.2(4) ?
C11 S1 C10 N2 . . . . -179.5(4) ?
C17 C16 C15 C14 . . . . -1.5(7) ?
C17 C16 C15 Br1 . . . . -179.8(3) ?
C16 C15 C14 C13 . . . . 1.7(7) ?
Br1 C15 C14 C13 . . . . -179.9(3) ?
C13 C12 C17 C16 . . . . -1.6(6) ?
C11 C12 C17 C16 . . . . 179.2(4) ?
C15 C16 C17 C12 . . . . 1.4(7) ?
C7 N1 C8 C9 . . . . -159.0(4) ?
C10 N2 C9 O2 . . . . -2.3(6) ?
C10 N2 C9 C8 . . . . -180.0(4) ?
N1 C8 C9 O2 . . . . -0.2(6) ?
N1 C8 C9 N2 . . . . 177.4(3) ?
N3 N4 C11 C12 . . . . 179.8(4) ?
N3 N4 C11 S1 . . . . -0.6(5) ?
C13 C12 C11 N4 . . . . -0.9(6) ?
C17 C12 C11 N4 . . . . 178.3(4) ?
C13 C12 C11 S1 . . . . 179.6(3) ?
C17 C12 C11 S1 . . . . -1.2(6) ?
C10 S1 C11 N4 . . . . 1.5(3) ?
C10 S1 C11 C12 . . . . -178.9(4) ?
C17 C12 C13 C14 . . . . 1.8(6) ?
C11 C12 C13 C14 . . . . -179.0(4) ?
C15 C14 C13 C12 . . . . -1.8(7) ?
C8 N1 C7 O1 . . . . 5.2(6) ?
C8 N1 C7 C6 . . . . -176.1(4) ?
C4 C5 C6 C1 . . . . 1.8(7) ?
C4 C5 C6 C7 . . . . -178.7(5) ?
O1 C7 C6 C5 . . . . 17.2(7) ?
N1 C7 C6 C5 . . . . -161.5(4) ?
O1 C7 C6 C1 . . . . -163.3(4) ?
N1 C7 C6 C1 . . . . 18.0(7) ?
C1 C2 C3 C4 . . . . 0.1(8) ?
C5 C4 C3 C2 . . . . 1.6(8) ?
C5 C6 C1 C2 . . . . 0.0(7) ?
C7 C6 C1 C2 . . . . -179.5(4) ?
C3 C2 C1 C6 . . . . -0.9(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741575
