#------------------------------------------------------------------------------
#$Date: 2025-11-29 23:12:29 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303953 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/07/7160737.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_7160737
loop_
_publ_author_name
'Balasubramani, Alagesan'
'Shivachalappa Salgar, Rupali'
'Lingamallu, Giribabu'
'Pabbaraja, Srihari'
'Mehta, Goverdhan'
_publ_section_title
;
 Stitching ynones with indolin-2-thiones: an eco-friendly reaction cascade
 towards functionalized thiopyrano[2,3-b]indoles and their
 inceptive optoelectronic profiling.
;
_journal_issue                   40
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9100
_journal_page_last               9104
_journal_paper_doi               10.1039/d5ob01279a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H13 Br F N S'
_chemical_formula_sum            'C23 H13 Br F N S'
_chemical_formula_weight         434.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                115.183(8)
_cell_angle_beta                 110.520(10)
_cell_angle_gamma                95.253(10)
_cell_formula_units_Z            2
_cell_length_a                   9.555(6)
_cell_length_b                   10.663(6)
_cell_length_c                   11.118(6)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.360
_cell_measurement_theta_min      2.244
_cell_volume                     920.5(9)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13731
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.363
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       'metallic brownish brown'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.411
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1521P)²+0.3925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2406
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01279a2.cif
_cod_data_source_block           KB1654_0m
_cod_depositor_comments
'Adding full bibliography for 7160736--7160737.cif.'
_cod_original_cell_volume        920.4(9)
_cod_database_code               7160737
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.649
_shelx_estimated_absorpt_t_max   0.704
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0587(6) 0.3129(5) 0.8723(5) 0.0432(11) Uani 1 1 d . . . . .
C2 C 1.0986(7) 0.3608(6) 1.0214(6) 0.0501(12) Uani 1 1 d . . . . .
C3 C 1.2487(8) 0.3983(6) 1.1252(6) 0.0625(16) Uani 1 1 d . . . . .
H3 H 1.269418 0.430019 1.223278 0.075 Uiso 1 1 calc R U . . .
C4 C 1.3672(8) 0.3883(7) 1.0826(7) 0.0688(17) Uani 1 1 d . . . . .
H4 H 1.469159 0.414138 1.152252 0.083 Uiso 1 1 calc R U . . .
C5 C 1.3361(7) 0.3401(8) 0.9372(7) 0.0718(17) Uani 1 1 d . . . . .
H5 H 1.416432 0.333410 0.907994 0.086 Uiso 1 1 calc R U . . .
C6 C 1.1848(6) 0.3020(7) 0.8357(6) 0.0605(15) Uani 1 1 d . . . . .
H6 H 1.165056 0.267042 0.737425 0.073 Uiso 1 1 calc R U . . .
C7 C 0.8975(5) 0.2778(5) 0.7592(5) 0.0396(10) Uani 1 1 d . . . . .
C8 C 0.5816(5) 0.2020(5) 0.6461(5) 0.0378(10) Uani 1 1 d . . . . .
C9 C 0.5883(5) 0.2088(5) 0.5194(5) 0.0379(10) Uani 1 1 d . . . . .
C10 C 0.7252(5) 0.2409(5) 0.5129(5) 0.0391(10) Uani 1 1 d . . . . .
C11 C 0.8720(5) 0.2785(5) 0.6290(5) 0.0414(11) Uani 1 1 d . . . . .
H11 H 0.959342 0.306064 0.617210 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3412(6) 0.1416(5) 0.4938(6) 0.0461(12) Uani 1 1 d . . . . .
C13 C 0.4247(5) 0.1683(5) 0.4190(5) 0.0413(11) Uani 1 1 d . . . . .
C14 C 0.7227(5) 0.2150(5) 0.3643(5) 0.0429(11) Uani 1 1 d D U . . .
C16 C 0.6872(6) 0.0493(7) 0.1205(5) 0.0552(13) Uani 1 1 d D U . . .
H16 H 0.660977 -0.042436 0.040985 0.066 Uiso 1 1 calc R U . A 1
C17 C 0.7221(7) 0.1657(7) 0.0993(6) 0.0574(13) Uani 1 1 d . U . . .
H17 H 0.723095 0.149216 0.010510 0.069 Uiso 1 1 calc R U . . .
C18 C 0.7540(7) 0.3000(7) 0.2047(6) 0.0589(13) Uani 1 1 d . U . . .
H18 H 0.775339 0.376259 0.187756 0.071 Uiso 1 1 calc R U . . .
C19 C 0.7562(6) 0.3298(6) 0.3408(6) 0.0517(12) Uani 1 1 d . U . . .
C20 C 0.1787(6) 0.1010(6) 0.4272(7) 0.0540(13) Uani 1 1 d . . . . .
H20 H 0.122662 0.083379 0.474721 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1035(6) 0.0876(6) 0.2911(8) 0.0649(17) Uani 1 1 d . . . . .
H21 H -0.004840 0.058464 0.245138 0.078 Uiso 1 1 calc R U . . .
C22 C 0.1843(6) 0.1162(6) 0.2199(7) 0.0589(15) Uani 1 1 d . . . . .
H22 H 0.129165 0.106688 0.127565 0.071 Uiso 1 1 calc R U . . .
C23 C 0.3459(6) 0.1588(6) 0.2833(6) 0.0499(12) Uani 1 1 d . . . . .
H23 H 0.399701 0.180278 0.235910 0.060 Uiso 1 1 calc R U . . .
N1 N 0.4408(5) 0.1628(4) 0.6336(5) 0.0476(10) Uani 1 1 d . . . . .
S1 S 0.74497(14) 0.23382(14) 0.79776(13) 0.0462(4) Uani 1 1 d . . . . .
C15 C 0.6876(4) 0.0561(6) 0.2479(4) 0.0385(12) Uani 0.936(6) 1 d D U P B 1
H15 H 0.669484 -0.023128 0.261281 0.046 Uiso 0.936(6) 1 calc R U P B 1
Br1 Br 0.7948(2) 0.52560(9) 0.48518(10) 0.0710(6) Uani 0.936(6) 1 d . . P B 1
C15D C 0.6917(6) 0.0733(15) 0.2549(10) 0.044(6) Uani 0.064(6) 1 d D U P B 2
H15D H 0.674325 -0.003647 0.271784 0.053 Uiso 0.064(6) 1 calc R U P B 2
Br1D Br 0.703(4) 0.501(3) 0.469(3) 0.133(9) Uani 0.064(6) 1 d . . P B 2
F1 F 0.9885(4) 0.3733(5) 1.0692(4) 0.0809(11) Uani 1 1 d . . . . .
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'
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 114.2(5) . . ?
C2 C1 C7 124.3(5) . . ?
C6 C1 C7 121.5(4) . . ?
F1 C2 C3 116.6(5) . . ?
F1 C2 C1 119.8(5) . . ?
C3 C2 C1 123.5(5) . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.1(7) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 123.6(6) . . ?
C5 C6 H6 118.2 . . ?
C1 C6 H6 118.2 . . ?
C11 C7 C1 121.2(4) . . ?
C11 C7 S1 121.9(4) . . ?
C1 C7 S1 116.9(3) . . ?
N1 C8 C9 115.2(4) . . ?
N1 C8 S1 121.6(3) . . ?
C9 C8 S1 123.2(3) . . ?
C10 C9 C13 134.8(4) . . ?
C10 C9 C8 122.1(4) . . ?
C13 C9 C8 103.1(4) . . ?
C9 C10 C11 123.5(4) . . ?
C9 C10 C14 119.0(4) . . ?
C11 C10 C14 116.9(4) . . ?
C7 C11 C10 125.6(4) . . ?
C7 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
C20 C12 N1 127.7(5) . . ?
C20 C12 C13 119.7(5) . . ?
N1 C12 C13 112.6(4) . . ?
C23 C13 C12 120.5(4) . . ?
C23 C13 C9 134.6(4) . . ?
C12 C13 C9 104.8(4) . . ?
C19 C14 C15D 120.1(7) . . ?
C19 C14 C15 122.6(4) . . ?
C19 C14 C10 121.1(4) . . ?
C15D C14 C10 118.7(7) . . ?
C15 C14 C10 116.2(4) . . ?
C15 C16 C17 126.6(5) . . ?
C15D C16 C17 120.0(8) . . ?
C15 C16 H16 116.7 . . ?
C17 C16 H16 116.7 . . ?
C18 C17 C16 120.6(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.6(5) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C18 118.7(5) . . ?
C14 C19 Br1 121.8(4) . . ?
C18 C19 Br1 119.4(4) . . ?
C14 C19 Br1D 109.9(9) . . ?
C18 C19 Br1D 125.2(8) . . ?
C21 C20 C12 118.7(5) . . ?
C21 C20 H20 120.6 . . ?
C12 C20 H20 120.6 . . ?
C20 C21 C22 121.7(5) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C23 121.4(5) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C13 C23 C22 118.0(5) . . ?
C13 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
C8 N1 C12 104.3(4) . . ?
C8 S1 C7 103.5(2) . . ?
C16 C15 C14 109.8(4) . . ?
C16 C15 H15 125.1 . . ?
C14 C15 H15 125.1 . . ?
C16 C15D C14 118.9(12) . . ?
C16 C15D H15D 120.5 . . ?
C14 C15D H15D 120.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.399(7) . ?
C1 C6 1.399(8) . ?
C1 C7 1.493(7) . ?
C2 F1 1.328(7) . ?
C2 C3 1.375(8) . ?
C3 C4 1.368(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.384(6) . ?
C7 S1 1.735(5) . ?
C8 N1 1.312(6) . ?
C8 C9 1.464(6) . ?
C8 S1 1.722(5) . ?
C9 C10 1.356(6) . ?
C9 C13 1.455(6) . ?
C10 C11 1.407(6) . ?
C10 C14 1.546(6) . ?
C11 H11 0.9300 . ?
C12 C20 1.394(7) . ?
C12 N1 1.413(7) . ?
C12 C13 1.426(7) . ?
C13 C23 1.383(7) . ?
C14 C19 1.388(7) . ?
C14 C15D 1.397(10) . ?
C14 C15 1.544(6) . ?
C16 C15 1.386(6) . ?
C16 C15D 1.389(10) . ?
C16 C17 1.390(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.326(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(8) . ?
C18 H18 0.9300 . ?
C19 Br1 1.914(6) . ?
C19 Br1D 2.02(3) . ?
C20 C21 1.365(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C15 H15 0.9300 . ?
C15D H15D 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -178.9(5) . . . . ?
C7 C1 C2 F1 2.0(8) . . . . ?
C6 C1 C2 C3 1.8(8) . . . . ?
C7 C1 C2 C3 -177.3(5) . . . . ?
F1 C2 C3 C4 -179.7(5) . . . . ?
C1 C2 C3 C4 -0.3(9) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C4 C5 C6 C1 1.8(10) . . . . ?
C2 C1 C6 C5 -2.5(8) . . . . ?
C7 C1 C6 C5 176.6(5) . . . . ?
C2 C1 C7 C11 158.0(5) . . . . ?
C6 C1 C7 C11 -21.0(7) . . . . ?
C2 C1 C7 S1 -22.9(6) . . . . ?
C6 C1 C7 S1 158.1(4) . . . . ?
N1 C8 C9 C10 -176.8(4) . . . . ?
S1 C8 C9 C10 0.1(6) . . . . ?
N1 C8 C9 C13 0.6(5) . . . . ?
S1 C8 C9 C13 177.5(3) . . . . ?
C13 C9 C10 C11 179.7(5) . . . . ?
C8 C9 C10 C11 -3.8(7) . . . . ?
C13 C9 C10 C14 -9.2(8) . . . . ?
C8 C9 C10 C14 167.3(4) . . . . ?
C1 C7 C11 C10 177.0(4) . . . . ?
S1 C7 C11 C10 -2.0(7) . . . . ?
C9 C10 C11 C7 5.0(8) . . . . ?
C14 C10 C11 C7 -166.3(5) . . . . ?
C20 C12 C13 C23 2.1(7) . . . . ?
N1 C12 C13 C23 -177.2(4) . . . . ?
C20 C12 C13 C9 179.4(4) . . . . ?
N1 C12 C13 C9 0.1(5) . . . . ?
C10 C9 C13 C23 -6.7(10) . . . . ?
C8 C9 C13 C23 176.4(5) . . . . ?
C10 C9 C13 C12 176.5(5) . . . . ?
C8 C9 C13 C12 -0.4(5) . . . . ?
C9 C10 C14 C19 107.8(5) . . . . ?
C11 C10 C14 C19 -80.5(6) . . . . ?
C9 C10 C14 C15D -74.6(6) . . . . ?
C11 C10 C14 C15D 97.1(5) . . . . ?
C9 C10 C14 C15 -74.6(5) . . . . ?
C11 C10 C14 C15 97.1(5) . . . . ?
C15 C16 C17 C18 -3.0(9) . . . . ?
C15D C16 C17 C18 -2.6(8) . . . . ?
C16 C17 C18 C19 1.0(9) . . . . ?
C15D C14 C19 C18 1.7(7) . . . . ?
C15 C14 C19 C18 1.8(7) . . . . ?
C10 C14 C19 C18 179.2(4) . . . . ?
C15 C14 C19 Br1 178.6(3) . . . . ?
C10 C14 C19 Br1 -3.9(6) . . . . ?
C15D C14 C19 Br1D 155.4(9) . . . . ?
C10 C14 C19 Br1D -27.1(10) . . . . ?
C17 C18 C19 C14 -0.6(8) . . . . ?
C17 C18 C19 Br1 -177.5(4) . . . . ?
C17 C18 C19 Br1D -149.9(12) . . . . ?
N1 C12 C20 C21 179.3(5) . . . . ?
C13 C12 C20 C21 0.1(7) . . . . ?
C12 C20 C21 C22 -1.4(8) . . . . ?
C20 C21 C22 C23 0.5(9) . . . . ?
C12 C13 C23 C22 -2.9(8) . . . . ?
C9 C13 C23 C22 -179.3(5) . . . . ?
C21 C22 C23 C13 1.7(8) . . . . ?
C9 C8 N1 C12 -0.6(5) . . . . ?
S1 C8 N1 C12 -177.5(3) . . . . ?
C20 C12 N1 C8 -179.0(5) . . . . ?
C13 C12 N1 C8 0.3(5) . . . . ?
N1 C8 S1 C7 178.9(4) . . . . ?
C9 C8 S1 C7 2.2(4) . . . . ?
C11 C7 S1 C8 -1.3(5) . . . . ?
C1 C7 S1 C8 179.7(3) . . . . ?
C17 C16 C15 C14 3.8(7) . . . . ?
C19 C14 C15 C16 -3.2(6) . . . . ?
C10 C14 C15 C16 179.3(4) . . . . ?
C17 C16 C15D C14 3.7(7) . . . . ?
C19 C14 C15D C16 -3.3(7) . . . . ?
C10 C14 C15D C16 179.2(4) . . . . ?
