#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/56/7155681.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_7155681
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 H10 Br N O S2'
_chemical_formula_weight         388.28
_chemical_name_systematic        4f
_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                 113.1330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1202(5)
_cell_length_b                   12.7017(3)
_cell_length_c                   14.3420(4)
_cell_measurement_reflns_used    7634
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.579
_cell_measurement_theta_min      0.419
_cell_volume                     3035.51(14)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40271
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  0.579
_exptl_absorpt_correction_T_min  0.419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1552.0
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.472
_refine_diff_density_min         -1.325
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         7634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0464
_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)+(0.0591P)²+5.2880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                3719
_reflns_number_total             7634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01033h2.cif
_cod_data_source_block           karuna1
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7155681
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 0.5373(2) 0.4911(3) 0.7223(3) 0.0573(12) Uani 1 1 d .
H1A H 0.4880 0.4760 0.6860 0.069 Uiso 1 1 calc R
H1B H 0.5518 0.5557 0.7354 0.069 Uiso 1 1 calc R
N2 N 0.0442(2) 0.2011(3) 0.2017(3) 0.0586(12) Uani 1 1 d .
H2A H -0.0055 0.2171 0.1690 0.070 Uiso 1 1 calc R
H2B H 0.0597 0.1369 0.2034 0.070 Uiso 1 1 calc R
O1 O 0.61005(19) 0.0748(2) 0.7600(3) 0.0571(9) Uani 1 1 d .
O2 O 0.1091(2) 0.6120(3) 0.3035(3) 0.0632(10) Uani 1 1 d .
S1 S 0.82212(7) 0.28720(10) 0.90092(10) 0.0495(3) Uani 1 1 d .
S2 S 0.69348(7) 0.44683(9) 0.82389(9) 0.0455(3) Uani 1 1 d .
S3 S 0.32610(7) 0.40314(10) 0.41091(11) 0.0578(4) Uani 1 1 d .
S4 S 0.20038(7) 0.24474(9) 0.30718(11) 0.0524(3) Uani 1 1 d .
Br1 Br 0.38985(3) 0.07119(4) 0.43641(4) 0.0629(2) Uani 1 1 d .
Br2 Br -0.11585(4) 0.63643(6) -0.02393(5) 0.0847(3) Uani 1 1 d .
C18 C 0.3201(3) 0.5382(4) 0.4293(4) 0.0484(12) Uani 1 1 d .
C19 C 0.3936(3) 0.5857(5) 0.4885(4) 0.0584(14) Uani 1 1 d .
H19 H 0.4403 0.5457 0.5145 0.070 Uiso 1 1 calc R
C20 C 0.3959(4) 0.6917(5) 0.5077(4) 0.0675(16) Uani 1 1 d .
H20 H 0.4441 0.7230 0.5491 0.081 Uiso 1 1 calc R
C21 C 0.3271(3) 0.7525(4) 0.4660(4) 0.0594(14) Uani 1 1 d .
H21 H 0.3296 0.8250 0.4758 0.071 Uiso 1 1 calc R
C22 C 0.2557(3) 0.7053(4) 0.4104(4) 0.0560(13) Uani 1 1 d .
H22 H 0.2095 0.7462 0.3851 0.067 Uiso 1 1 calc R
C23 C 0.2498(3) 0.5970(4) 0.3902(3) 0.0445(11) Uani 1 1 d .
C25 C 0.1614(3) 0.4407(3) 0.3099(3) 0.0406(11) Uani 1 1 d .
C26 C 0.2266(3) 0.3752(4) 0.3409(4) 0.0448(11) Uani 1 1 d .
C27 C 0.0869(3) 0.3842(4) 0.2580(3) 0.0420(11) Uani 1 1 d .
C24 C 0.1686(3) 0.5537(4) 0.3313(4) 0.0478(12) Uani 1 1 d .
C29 C 0.0046(3) 0.4294(4) 0.2096(3) 0.0416(11) Uani 1 1 d .
C30 C -0.0145(3) 0.5024(4) 0.1300(3) 0.0465(12) Uani 1 1 d .
H30 H 0.0250 0.5266 0.1090 0.056 Uiso 1 1 calc R
C31 C -0.0921(3) 0.5375(4) 0.0836(4) 0.0495(12) Uani 1 1 d .
C32 C -0.1519(3) 0.5054(4) 0.1125(4) 0.0498(12) Uani 1 1 d .
H32 H -0.2042 0.5298 0.0791 0.060 Uiso 1 1 calc R
C33 C -0.1331(3) 0.4363(4) 0.1918(4) 0.0513(13) Uani 1 1 d .
H33 H -0.1728 0.4148 0.2136 0.062 Uiso 1 1 calc R
C28 C 0.0990(3) 0.2785(4) 0.2514(4) 0.0459(12) Uani 1 1 d .
C1 C 0.8181(3) 0.1500(3) 0.9076(3) 0.0411(11) Uani 1 1 d .
C2 C 0.8906(3) 0.0998(4) 0.9652(4) 0.0523(13) Uani 1 1 d .
H2 H 0.9371 0.1393 0.9957 0.063 Uiso 1 1 calc R
C3 C 0.8928(3) -0.0070(4) 0.9767(4) 0.0610(15) Uani 1 1 d .
H3 H 0.9409 -0.0399 1.0158 0.073 Uiso 1 1 calc R
C4 C 0.8242(3) -0.0666(4) 0.9306(5) 0.0669(16) Uani 1 1 d .
H4 H 0.8261 -0.1393 0.9388 0.080 Uiso 1 1 calc R
C7 C 0.6680(3) 0.1351(3) 0.7993(3) 0.0389(10) Uani 1 1 d .
C10 C 0.5825(2) 0.3049(3) 0.7471(3) 0.0387(10) Uani 1 1 d .
C8 C 0.6584(2) 0.2492(3) 0.7918(3) 0.0359(10) Uani 1 1 d .
C9 C 0.7220(3) 0.3162(3) 0.8344(3) 0.0387(10) Uani 1 1 d .
C11 C 0.5927(3) 0.4122(4) 0.7590(3) 0.0422(11) Uani 1 1 d .
C12 C 0.5022(2) 0.2585(3) 0.6914(3) 0.0382(10) Uani 1 1 d .
C13 C 0.4856(3) 0.1957(3) 0.6060(3) 0.0399(10) Uani 1 1 d .
H13 H 0.5264 0.1799 0.5843 0.048 Uiso 1 1 calc R
C14 C 0.4094(3) 0.1567(3) 0.5531(4) 0.0447(12) Uani 1 1 d .
C15 C 0.3470(3) 0.1776(4) 0.5823(4) 0.0478(12) Uani 1 1 d .
H15 H 0.2958 0.1513 0.5456 0.057 Uiso 1 1 calc R
C16 C 0.3627(3) 0.2392(4) 0.6679(4) 0.0510(13) Uani 1 1 d .
H16 H 0.3216 0.2542 0.6893 0.061 Uiso 1 1 calc R
C17 C 0.4393(3) 0.2788(4) 0.7223(4) 0.0468(12) Uani 1 1 d .
H17 H 0.4489 0.3192 0.7799 0.056 Uiso 1 1 calc R
C34 C -0.0555(3) 0.3978(4) 0.2401(4) 0.0502(12) Uani 1 1 d .
H34 H -0.0439 0.3504 0.2934 0.060 Uiso 1 1 calc R
C6 C 0.7480(2) 0.0908(3) 0.8595(3) 0.0372(10) Uani 1 1 d .
C5 C 0.7537(3) -0.0184(4) 0.8730(4) 0.0536(13) Uani 1 1 d .
H5 H 0.7081 -0.0593 0.8418 0.064 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'
Cl Cl 0.1484 0.1585 '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
C9 S1 C1 100.7(2)
C9 S2 C11 91.1(2)
C26 S3 C18 100.2(2)
C26 S4 C28 91.0(2)
C23 C18 C19 121.0(5)
C23 C18 S3 124.6(4)
C19 C18 S3 114.4(4)
C20 C19 C18 119.3(5)
C19 C20 C21 120.6(5)
C22 C21 C20 119.5(5)
C21 C22 C23 122.1(5)
C18 C23 C22 117.4(5)
C18 C23 C24 125.2(4)
C22 C23 C24 117.4(4)
C26 C25 C27 112.2(4)
C26 C25 C24 122.2(4)
C27 C25 C24 125.6(4)
C25 C26 S3 129.6(4)
C25 C26 S4 112.4(3)
S3 C26 S4 117.9(3)
C28 C27 C25 112.2(4)
C28 C27 C29 120.2(4)
C25 C27 C29 127.4(4)
O2 C24 C25 121.7(4)
O2 C24 C23 120.3(4)
C25 C24 C23 118.0(4)
C34 C29 C30 118.4(4)
C34 C29 C27 120.6(4)
C30 C29 C27 121.0(4)
C31 C30 C29 119.2(5)
C32 C31 C30 122.7(5)
C32 C31 Br2 119.3(4)
C30 C31 Br2 118.0(4)
C31 C32 C33 118.4(4)
C32 C33 C34 120.8(5)
C27 C28 N2 129.2(4)
C27 C28 S4 112.1(3)
N2 C28 S4 118.5(4)
C2 C1 C6 120.3(4)
C2 C1 S1 115.9(4)
C6 C1 S1 123.9(3)
C3 C2 C1 120.0(5)
C2 C3 C4 120.5(5)
C5 C4 C3 119.7(5)
O1 C7 C8 121.6(4)
O1 C7 C6 119.5(4)
C8 C7 C6 118.9(4)
C11 C10 C8 111.7(4)
C11 C10 C12 121.1(4)
C8 C10 C12 127.1(4)
C9 C8 C10 112.3(4)
C9 C8 C7 122.0(4)
C10 C8 C7 125.6(4)
C8 C9 S1 129.2(3)
C8 C9 S2 112.8(3)
S1 C9 S2 117.9(2)
N1 C11 C10 129.4(4)
N1 C11 S2 118.4(3)
C10 C11 S2 112.1(3)
C13 C12 C17 117.6(4)
C13 C12 C10 121.9(4)
C17 C12 C10 120.5(4)
C14 C13 C12 120.8(4)
C15 C14 C13 121.8(5)
C15 C14 Br1 119.0(3)
C13 C14 Br1 119.2(4)
C14 C15 C16 118.1(4)
C15 C16 C17 120.8(5)
C16 C17 C12 120.9(5)
C29 C34 C33 120.6(5)
C5 C6 C1 117.4(4)
C5 C6 C7 117.5(4)
C1 C6 C7 125.0(4)
C4 C5 C6 122.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.369(6)
N2 C28 1.379(6)
O1 C7 1.242(5)
O2 C24 1.237(6)
S1 C9 1.725(4)
S1 C1 1.748(5)
S2 C9 1.727(4)
S2 C11 1.749(4)
S3 C26 1.721(5)
S3 C18 1.746(5)
S4 C26 1.739(5)
S4 C28 1.745(5)
Br1 C14 1.908(5)
Br2 C31 1.903(5)
C18 C23 1.391(7)
C18 C19 1.404(7)
C19 C20 1.372(8)
C20 C21 1.388(8)
C21 C22 1.363(7)
C22 C23 1.401(7)
C23 C24 1.485(7)
C25 C26 1.369(6)
C25 C27 1.450(6)
C25 C24 1.463(6)
C27 C28 1.370(6)
C27 C29 1.490(6)
C29 C34 1.383(7)
C29 C30 1.404(6)
C30 C31 1.373(6)
C31 C32 1.366(7)
C32 C33 1.370(7)
C33 C34 1.390(7)
C1 C2 1.400(6)
C1 C6 1.402(6)
C2 C3 1.365(7)
C3 C4 1.383(8)
C4 C5 1.363(7)
C7 C8 1.458(6)
C7 C6 1.477(6)
C10 C11 1.377(6)
C10 C8 1.452(6)
C10 C12 1.480(6)
C8 C9 1.370(6)
C12 C13 1.392(6)
C12 C17 1.398(6)
C13 C14 1.380(6)
C14 C15 1.376(7)
C15 C16 1.388(7)
C16 C17 1.392(6)
C6 C5 1.398(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193013
