#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226156.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_2226156
loop_
_publ_author_name
'Arshad, Afsheen'
'Osman, Hasnah'
'Chan, Kit Lam'
'Goh, Jia Hao'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-1-[1-(6-Bromo-2-oxo-2H-chromen-3-yl)ethylidene]thiosemicarbazide
;
_journal_coeditor_code           HB5461
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1491
_journal_page_last               o1492
_journal_paper_doi               10.1107/S1600536810019240
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 Br N3 O2 S'
_chemical_formula_moiety         'C12 H10 Br N3 O2 S'
_chemical_formula_sum            'C12 H10 Br N3 O2 S'
_chemical_formula_weight         340.20
_chemical_name_systematic
;
(E)-1-[1-(6-Bromo-2-oxo-2H-chromen-3-
yl)ethylidene]thiosemicarbazide
;
_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                106.697(2)
_cell_angle_beta                 95.095(2)
_cell_angle_gamma                98.925(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3796(6)
_cell_length_b                   8.1260(7)
_cell_length_c                   13.3756(12)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.06
_cell_measurement_theta_min      2.66
_cell_volume                     649.57(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19355
_diffrn_reflns_theta_full        33.50
_diffrn_reflns_theta_max         33.50
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.325
_exptl_absorpt_correction_T_max  0.637
_exptl_absorpt_correction_T_min  0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.556
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0210
_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+0.0443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                4733
_reflns_number_total             5036
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5461.cif
_cod_data_source_block           I
_cod_database_code               2226156
_cod_database_fobs_code          2226156
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 0.831903(19) -0.130575(15) 0.134917(9) 0.01986(5) Uani d . 1 . .
S S1 -0.52737(6) 0.26734(4) 0.52668(3) 0.02208(7) Uani d . 1 . .
O O1 0.39540(15) 0.46915(12) 0.12143(7) 0.01830(16) Uani d . 1 . .
O O2 0.14155(19) 0.62282(15) 0.15561(9) 0.0270(2) Uani d . 1 . .
N N1 -0.08889(17) 0.33908(13) 0.34997(8) 0.01559(17) Uani d . 1 . .
N N2 -0.24110(18) 0.37175(14) 0.41584(8) 0.01611(17) Uani d . 1 . .
N N3 -0.2610(2) 0.08895(15) 0.41915(9) 0.0204(2) Uani d . 1 . .
C C1 0.2259(2) 0.50976(16) 0.17462(10) 0.0177(2) Uani d . 1 . .
C C2 0.48940(19) 0.32942(15) 0.12434(9) 0.01509(18) Uani d . 1 . .
C C3 0.6564(2) 0.29964(17) 0.06532(10) 0.0179(2) Uani d . 1 . .
H H3A 0.7011 0.3720 0.0255 0.022 Uiso calc R 1 . .
C C4 0.75479(19) 0.15951(17) 0.06722(9) 0.0178(2) Uani d . 1 . .
H H4A 0.8675 0.1375 0.0288 0.021 Uiso calc R 1 . .
C C5 0.68424(19) 0.05161(16) 0.12688(9) 0.01630(19) Uani d . 1 . .
C C6 0.51529(19) 0.07869(15) 0.18374(9) 0.01632(19) Uani d . 1 . .
H H6A 0.4670 0.0031 0.2210 0.020 Uiso calc R 1 . .
C C7 0.41777(18) 0.22285(15) 0.18420(9) 0.01446(18) Uani d . 1 . .
C C8 0.25545(18) 0.27089(15) 0.24813(9) 0.01512(18) Uani d . 1 . .
H H8A 0.2113 0.2048 0.2915 0.018 Uiso calc R 1 . .
C C9 0.16407(18) 0.41112(15) 0.24698(9) 0.01454(18) Uani d . 1 . .
C C10 -0.00056(18) 0.46198(15) 0.31560(9) 0.01494(18) Uani d . 1 . .
C C11 -0.33190(19) 0.23856(15) 0.44883(9) 0.01633(19) Uani d . 1 . .
C C12 -0.0508(2) 0.64307(16) 0.34349(10) 0.0196(2) Uani d . 1 . .
H H12A -0.0674 0.6814 0.4167 0.029 Uiso calc R 1 . .
H H12B -0.1814 0.6417 0.3013 0.029 Uiso calc R 1 . .
H H12C 0.0641 0.7218 0.3302 0.029 Uiso calc R 1 . .
H H1N2 -0.308(5) 0.438(4) 0.420(3) 0.060(9) Uiso d . 1 . .
H H1N3 -0.317(3) 0.005(3) 0.4346(16) 0.019(4) Uiso d . 1 . .
H H2N3 -0.164(5) 0.094(4) 0.383(3) 0.057(9) Uiso d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C1 . . 122.75(9) ?
C10 N1 N2 . . 119.10(10) ?
C11 N2 N1 . . 117.19(10) ?
C11 N2 H1N2 . . 111(3) ?
N1 N2 H1N2 . . 128(3) ?
C11 N3 H1N3 . . 119.9(15) ?
C11 N3 H2N3 . . 112(2) ?
H1N3 N3 H2N3 . . 128(3) ?
O2 C1 O1 . . 116.08(11) ?
O2 C1 C9 . . 126.61(11) ?
O1 C1 C9 . . 117.31(10) ?
O1 C2 C3 . . 117.34(10) ?
O1 C2 C7 . . 120.50(10) ?
C3 C2 C7 . . 122.16(10) ?
C4 C3 C2 . . 118.48(11) ?
C4 C3 H3A . . 120.8 ?
C2 C3 H3A . . 120.8 ?
C3 C4 C5 . . 119.89(10) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
C6 C5 C4 . . 121.73(10) ?
C6 C5 Br1 . . 119.11(9) ?
C4 C5 Br1 . . 119.11(9) ?
C5 C6 C7 . . 118.75(10) ?
C5 C6 H6A . . 120.6 ?
C7 C6 H6A . . 120.6 ?
C2 C7 C6 . . 118.95(10) ?
C2 C7 C8 . . 118.13(10) ?
C6 C7 C8 . . 122.83(10) ?
C9 C8 C7 . . 121.52(10) ?
C9 C8 H8A . . 119.2 ?
C7 C8 H8A . . 119.2 ?
C8 C9 C1 . . 119.13(10) ?
C8 C9 C10 . . 120.96(10) ?
C1 C9 C10 . . 119.90(10) ?
N1 C10 C9 . . 113.79(10) ?
N1 C10 C12 . . 124.38(10) ?
C9 C10 C12 . . 121.81(10) ?
N3 C11 N2 . . 117.80(11) ?
N3 C11 S1 . . 122.45(9) ?
N2 C11 S1 . . 119.74(9) ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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 C5 . 1.8965(11) ?
S1 C11 . 1.6957(12) ?
O1 C2 . 1.3722(14) ?
O1 C1 . 1.3770(14) ?
O2 C1 . 1.2091(15) ?
N1 C10 . 1.2890(15) ?
N1 N2 . 1.3738(14) ?
N2 C11 . 1.3516(15) ?
N2 H1N2 . 0.73(3) ?
N3 C11 . 1.3288(15) ?
N3 H1N3 . 0.81(2) ?
N3 H2N3 . 0.82(3) ?
C1 C9 . 1.4665(16) ?
C2 C3 . 1.3917(16) ?
C2 C7 . 1.3930(15) ?
C3 C4 . 1.3879(17) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3969(17) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3827(16) ?
C6 C7 . 1.4079(15) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.4307(16) ?
C8 C9 . 1.3613(15) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.4846(16) ?
C10 C12 . 1.5033(16) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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
N3 H2N3 N1 . 0.82(3) 2.15(3) 2.6004(17) 114(3) yes
N2 H1N2 S1 2_466 0.73(3) 2.70(3) 3.4094(13) 165(3) yes
N3 H1N3 S1 2_456 0.81(2) 2.49(2) 3.3010(13) 175.6(19) yes
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 N1 N2 C11 . . . . 179.07(11) ?
C2 O1 C1 O2 . . . . -171.47(12) ?
C2 O1 C1 C9 . . . . 7.73(18) ?
C1 O1 C2 C3 . . . . 178.59(11) ?
C1 O1 C2 C7 . . . . -1.23(18) ?
O1 C2 C3 C4 . . . . 179.76(11) ?
C7 C2 C3 C4 . . . . -0.43(19) ?
C2 C3 C4 C5 . . . . 0.48(19) ?
C3 C4 C5 C6 . . . . 0.93(19) ?
C3 C4 C5 Br1 . . . . -176.32(9) ?
C4 C5 C6 C7 . . . . -2.35(18) ?
Br1 C5 C6 C7 . . . . 174.90(9) ?
O1 C2 C7 C6 . . . . 178.81(11) ?
C3 C2 C7 C6 . . . . -0.99(18) ?
O1 C2 C7 C8 . . . . -4.54(17) ?
C3 C2 C7 C8 . . . . 175.65(11) ?
C5 C6 C7 C2 . . . . 2.34(18) ?
C5 C6 C7 C8 . . . . -174.14(11) ?
C2 C7 C8 C9 . . . . 3.45(17) ?
C6 C7 C8 C9 . . . . 179.96(12) ?
C7 C8 C9 C1 . . . . 3.09(18) ?
C7 C8 C9 C10 . . . . -178.55(11) ?
O2 C1 C9 C8 . . . . 170.56(14) ?
O1 C1 C9 C8 . . . . -8.54(18) ?
O2 C1 C9 C10 . . . . -7.8(2) ?
O1 C1 C9 C10 . . . . 173.08(11) ?
N2 N1 C10 C9 . . . . 178.83(10) ?
N2 N1 C10 C12 . . . . 0.63(18) ?
C8 C9 C10 N1 . . . . -18.82(16) ?
C1 C9 C10 N1 . . . . 159.52(11) ?
C8 C9 C10 C12 . . . . 159.43(12) ?
C1 C9 C10 C12 . . . . -22.22(17) ?
N1 N2 C11 N3 . . . . 2.93(17) ?
N1 N2 C11 S1 . . . . -177.80(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7890365
