#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/56/7155680.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7155680
loop_
_publ_author_name
'Mahato, Karuna'
'Ray Bagdi, Prasanta'
'Khan, Abu Taleb'
_publ_section_title
;
 K2CO3 catalyzed regioselective synthesis of
 thieno[2,3-b]thiochromen-4-one oximes: Access to the corresponding Amine
 and Nitroso derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01033H
_journal_year                    2017
_chemical_formula_sum            'C17 H9 N O2 S2'
_chemical_formula_weight         323.37
_chemical_name_systematic        5a
_chemical_properties_physical    Moisture-sensitive
_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
_audit_update_record
;
2016-02-18 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.132(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3128(3)
_cell_length_b                   18.0467(9)
_cell_length_c                   12.6157(5)
_cell_measurement_reflns_used    3698
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.936
_cell_measurement_theta_min      0.900
_cell_volume                     1429.02(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6216
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0203P)²+0.8107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                2306
_reflns_number_total             3698
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01033h2.cif
_cod_data_source_block           exp_2302
_cod_original_cell_volume        1429.03(11)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7155680
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.0007(4) 0.34637(13) 0.27378(19) 0.0493(6) Uani 1 1 d .
O1 O 0.2589(3) 0.44990(12) 0.08165(16) 0.0616(6) Uani 1 1 d .
O2 O 1.1510(3) 0.35707(14) 0.34491(18) 0.0686(7) Uani 1 1 d .
S1 S 0.48115(11) 0.56508(4) 0.38575(5) 0.0453(2) Uani 1 1 d .
S2 S 0.83396(10) 0.45906(4) 0.38175(5) 0.0413(2) Uani 1 1 d .
C1 C 0.2472(4) 0.57999(14) 0.30044(19) 0.0350(6) Uani 1 1 d .
C2 C 0.1192(4) 0.63828(15) 0.3304(2) 0.0469(7) Uani 1 1 d .
H2 H 0.1623 0.6665 0.3905 0.056 Uiso 1 1 calc R
C3 C -0.0704(5) 0.65347(16) 0.2702(3) 0.0531(8) Uani 1 1 d .
H3 H -0.1548 0.6923 0.2898 0.064 Uiso 1 1 calc R
C4 C -0.1376(4) 0.61149(16) 0.1805(2) 0.0477(7) Uani 1 1 d .
H4 H -0.2678 0.6212 0.1413 0.057 Uiso 1 1 calc R
C5 C -0.0094(4) 0.55541(15) 0.1503(2) 0.0390(6) Uani 1 1 d .
H5 H -0.0535 0.5279 0.0897 0.047 Uiso 1 1 calc R
C6 C 0.1856(4) 0.53884(13) 0.20874(19) 0.0325(5) Uani 1 1 d .
C7 C 0.3149(4) 0.47860(14) 0.1676(2) 0.0350(6) Uani 1 1 d .
C8 C 0.5125(4) 0.45508(13) 0.23221(18) 0.0300(5) Uani 1 1 d .
C9 C 0.5913(4) 0.49145(14) 0.32538(19) 0.0340(6) Uani 1 1 d .
C10 C 0.8338(4) 0.39513(14) 0.27835(19) 0.0354(6) Uani 1 1 d .
C11 C 0.6541(4) 0.39807(13) 0.20528(19) 0.0311(5) Uani 1 1 d .
C12 C 0.6198(4) 0.34624(13) 0.11376(19) 0.0326(6) Uani 1 1 d .
C13 C 0.4364(4) 0.30244(14) 0.1006(2) 0.0375(6) Uani 1 1 d .
H13 H 0.3351 0.3067 0.1486 0.045 Uiso 1 1 calc R
C14 C 0.4043(4) 0.25299(15) 0.0173(2) 0.0430(7) Uani 1 1 d .
H14 H 0.2827 0.2236 0.0100 0.052 Uiso 1 1 calc R
C15 C 0.5526(4) 0.24685(15) -0.0558(2) 0.0455(7) Uani 1 1 d .
H15 H 0.5296 0.2140 -0.1126 0.055 Uiso 1 1 calc R
C16 C 0.7341(4) 0.28969(16) -0.0438(2) 0.0474(7) Uani 1 1 d .
H16 H 0.8336 0.2857 -0.0929 0.057 Uiso 1 1 calc R
C17 C 0.7697(4) 0.33876(15) 0.0411(2) 0.0404(6) Uani 1 1 d .
H17 H 0.8941 0.3667 0.0494 0.048 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 N1 C10 113.4(2)
C9 S1 C1 101.60(12)
C9 S2 C10 89.22(12)
C6 C1 C2 120.3(2)
C6 C1 S1 124.72(19)
C2 C1 S1 114.9(2)
C3 C2 C1 119.6(3)
C2 C3 C4 120.8(3)
C5 C4 C3 119.3(3)
C4 C5 C6 121.5(3)
C1 C6 C5 118.4(2)
C1 C6 C7 124.4(2)
C5 C6 C7 117.3(2)
O1 C7 C8 121.1(2)
O1 C7 C6 120.2(2)
C8 C7 C6 118.7(2)
C9 C8 C11 111.4(2)
C9 C8 C7 122.4(2)
C11 C8 C7 126.1(2)
C8 C9 S1 128.00(19)
C8 C9 S2 114.26(19)
S1 C9 S2 117.69(14)
N1 C10 C11 124.9(2)
N1 C10 S2 120.99(19)
C11 C10 S2 114.10(18)
C10 C11 C8 111.0(2)
C10 C11 C12 122.4(2)
C8 C11 C12 126.6(2)
C13 C12 C17 118.7(2)
C13 C12 C11 120.0(2)
C17 C12 C11 121.3(2)
C14 C13 C12 120.6(2)
C13 C14 C15 120.3(2)
C16 C15 C14 119.7(3)
C15 C16 C17 120.4(2)
C16 C17 C12 120.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.249(3)
N1 C10 1.379(3)
O1 C7 1.219(3)
S1 C9 1.715(3)
S1 C1 1.753(3)
S2 C9 1.721(2)
S2 C10 1.741(3)
C1 C6 1.395(3)
C1 C2 1.403(3)
C2 C3 1.375(4)
C3 C4 1.390(4)
C4 C5 1.374(4)
C5 C6 1.398(3)
C6 C7 1.486(3)
C7 C8 1.478(3)
C8 C9 1.391(3)
C8 C11 1.428(3)
C10 C11 1.384(3)
C11 C12 1.484(3)
C12 C13 1.397(3)
C12 C17 1.393(3)
C13 C14 1.378(3)
C14 C15 1.387(3)
C15 C16 1.377(4)
C16 C17 1.389(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193012
