#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204819.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_2204819
loop_
_publ_author_name
'Jian-Guo Yang'
'Fu-You Pan'
_publ_section_title
;
 3-[(4-Bromo-2-thienyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2342
_journal_page_last               o2344
_journal_paper_doi               10.1107/S1600536804026613
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C8 H6 Br N5 O S'
_chemical_formula_moiety         'C8 H6 Br N5 O S'
_chemical_formula_sum            'C8 H6 Br N5 O S'
_chemical_formula_weight         300.15
_chemical_name_systematic
;
3-[(4-Bromo-2-thienyl)methylenehydrazinocarboxyl]-1H-1,2,4-triazole
;
_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                 100.312(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3236(10)
_cell_length_b                   7.6535(10)
_cell_length_c                   18.761(3)
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.991
_cell_measurement_theta_min      4.414
_cell_volume                     1034.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_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  0.1418
_diffrn_reflns_av_sigmaI/netI    0.1133
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5711
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.159
_exptl_absorpt_correction_T_max  0.459
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.997
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0483
_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)+(0.0562P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                1698
_reflns_number_total             2242
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6294.cif
_cod_data_source_block           I
_cod_original_cell_volume        1034.6(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204819
_cod_database_fobs_code          2204819
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_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_type_symbol
Br 1.04858(7) 1.62849(5) 1.13621(2) 0.0425(2) Uani d . 1 Br
S1 0.8817(2) 1.08789(15) 1.15594(6) 0.0486(4) Uani d . 1 S
O1 0.6319(5) 0.9003(4) 0.87074(15) 0.0394(8) Uani d . 1 O
N1 0.6310(5) 0.7603(4) 0.97811(16) 0.0310(8) Uani d . 1 N
N2 0.7021(5) 0.8842(4) 1.02899(16) 0.0309(8) Uani d . 1 N
N3 0.4901(5) 0.4569(4) 0.90244(16) 0.0328(8) Uani d . 1 N
N4 0.5102(5) 0.5966(4) 0.79821(17) 0.0351(8) Uani d . 1 N
N5 0.4540(6) 0.4308(5) 0.78557(17) 0.0378(9) Uani d D 1 N
C1 0.6015(5) 0.7703(5) 0.90607(19) 0.0277(8) Uani d . 1 C
C2 0.5311(6) 0.6061(5) 0.86830(19) 0.0286(8) Uani d . 1 C
C3 0.4451(7) 0.3505(6) 0.8471(2) 0.0382(10) Uani d . 1 C
C4 0.7617(6) 1.0304(5) 1.0100(2) 0.0341(9) Uani d . 1 C
C5 0.8428(6) 1.1503(5) 1.0661(2) 0.0312(9) Uani d . 1 C
C6 0.8940(6) 1.3176(6) 1.0586(2) 0.0335(9) Uani d . 1 C
C7 0.9648(6) 1.3961(5) 1.1264(2) 0.0314(9) Uani d . 1 C
C8 0.9702(7) 1.2892(6) 1.1825(2) 0.0450(12) Uani d . 1 C
H1 0.602(6) 0.675(6) 0.999(2) 0.022(10) Uiso d . 1 H
H3 0.426(6) 0.225(7) 0.853(2) 0.034(12) Uiso d . 1 H
H4 0.753(5) 1.067(6) 0.963(2) 0.028(11) Uiso d . 1 H
H5 0.456(7) 0.398(5) 0.7444(14) 0.046(14) Uiso d D 1 H
H6 0.870(6) 1.385(5) 1.011(3) 0.034(12) Uiso d . 1 H
H8 1.007(6) 1.310(6) 1.228(2) 0.030(11) Uiso d . 1 H
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
Br 0.0614(3) 0.0278(3) 0.0378(3) -0.0086(2) 0.0077(2) -0.00649(16)
S1 0.0836(10) 0.0297(6) 0.0269(5) -0.0129(6) -0.0052(6) 0.0039(4)
O1 0.068(2) 0.0234(14) 0.0245(14) -0.0085(14) 0.0028(14) 0.0010(10)
N1 0.048(2) 0.0220(17) 0.0211(15) -0.0078(16) 0.0027(14) -0.0004(12)
N2 0.0440(19) 0.0238(17) 0.0227(16) -0.0028(15) 0.0001(15) -0.0039(12)
N3 0.052(2) 0.0242(18) 0.0224(16) -0.0071(16) 0.0063(15) -0.0005(12)
N4 0.055(2) 0.0223(17) 0.0269(16) -0.0035(15) 0.0036(16) -0.0019(12)
N5 0.064(2) 0.0285(18) 0.0204(16) -0.0105(18) 0.0070(16) -0.0081(13)
C1 0.035(2) 0.0209(19) 0.0259(18) 0.0031(16) 0.0026(16) -0.0006(14)
C2 0.041(2) 0.0204(18) 0.0240(18) 0.0027(17) 0.0058(16) -0.0011(13)
C3 0.057(3) 0.025(2) 0.032(2) -0.011(2) 0.009(2) -0.0064(15)
C4 0.049(3) 0.030(2) 0.0217(19) -0.0046(19) 0.0034(17) -0.0027(15)
C5 0.046(2) 0.024(2) 0.0225(18) -0.0004(18) 0.0028(17) -0.0013(14)
C6 0.044(2) 0.029(2) 0.0263(19) -0.0036(19) 0.0039(18) -0.0001(16)
C7 0.039(2) 0.028(2) 0.0268(19) -0.0008(18) 0.0038(17) -0.0048(15)
C8 0.072(3) 0.033(3) 0.026(2) -0.011(2) -0.001(2) -0.0042(17)
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'
S S 0.1246 0.1234 '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
C8 S1 C5 91.3(2)
C1 N1 N2 129.4(3)
C1 N1 H1 123(3)
N2 N1 H1 108(3)
C4 N2 N1 121.1(3)
C3 N3 C2 101.1(3)
C2 N4 N5 102.0(3)
C3 N5 N4 110.3(3)
C3 N5 H5 134(3)
N4 N5 H5 114(3)
O1 C1 N1 125.3(4)
O1 C1 C2 120.3(3)
N1 C1 C2 114.4(3)
N4 C2 N3 115.6(3)
N4 C2 C1 119.8(3)
N3 C2 C1 124.6(3)
N3 C3 N5 111.0(4)
N3 C3 H3 122(2)
N5 C3 H3 126(2)
N2 C4 C5 118.1(3)
N2 C4 H4 124(3)
C5 C4 H4 117(3)
C6 C5 C4 127.9(4)
C6 C5 S1 111.3(3)
C4 C5 S1 120.8(3)
C5 C6 C7 111.9(4)
C5 C6 H6 125(2)
C7 C6 H6 123(2)
C8 C7 C6 113.8(4)
C8 C7 Br 122.8(3)
C6 C7 Br 123.4(3)
C7 C8 S1 111.6(3)
C7 C8 H8 129(3)
S1 C8 H8 119(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C7 1.880(4) yes
S1 C8 1.711(5) yes
S1 C5 1.726(4) yes
O1 C1 1.238(5) yes
N1 C1 1.332(5) yes
N1 N2 1.380(4) yes
N1 H1 0.81(4) ?
N2 C4 1.275(5) yes
N3 C3 1.315(5) yes
N3 C2 1.368(5) yes
N4 C2 1.298(5) yes
N4 N5 1.342(5) ?
N5 C3 1.319(6) yes
N5 H5 0.815(19) ?
C1 C2 1.489(5) ?
C3 H3 0.98(5) ?
C4 C5 1.441(5) yes
C4 H4 0.91(4) ?
C5 C6 1.349(6) yes
C6 C7 1.417(5) yes
C6 H6 1.01(5) ?
C7 C8 1.329(6) yes
C8 H8 0.86(4) ?
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
N5 H5 N4 2_646 0.815(19) 2.47(4) 3.038(5) 128(4)
N5 H5 O1 2_646 0.815(19) 2.14(3) 2.897(4) 154(5)
N1 H1 N3 3_667 0.81(4) 2.30(4) 3.047(5) 152(4)
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
C1 N1 N2 C4 -4.4(7)
C2 N4 N5 C3 -0.3(5)
N2 N1 C1 O1 -1.2(7)
N2 N1 C1 C2 177.1(4)
N5 N4 C2 N3 -0.7(5)
N5 N4 C2 C1 177.4(4)
C3 N3 C2 N4 1.3(5)
C3 N3 C2 C1 -176.6(4)
O1 C1 C2 N4 3.4(6)
N1 C1 C2 N4 -175.0(4)
O1 C1 C2 N3 -178.7(4)
N1 C1 C2 N3 2.9(6)
C2 N3 C3 N5 -1.5(5)
N4 N5 C3 N3 1.2(6)
N1 N2 C4 C5 -176.9(4)
N2 C4 C5 C6 -171.5(5)
N2 C4 C5 S1 7.1(6)
C8 S1 C5 C6 -0.8(4)
C8 S1 C5 C4 -179.6(4)
C4 C5 C6 C7 178.6(4)
S1 C5 C6 C7 -0.2(5)
C5 C6 C7 C8 1.4(6)
C5 C6 C7 Br -179.8(3)
C6 C7 C8 S1 -2.0(6)
Br C7 C8 S1 179.3(3)
C5 S1 C8 C7 1.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173786
