Stitching ynones with indolin-2-thiones: an eco-friendly reaction cascade towards functionalized thiopyrano[2,3-<i>b</i>]indoles and their inceptive optoelectronic profiling.
Balasubramani, Alagesan; Shivachalappa Salgar, Rupali; Lingamallu, Giribabu; Pabbaraja, Srihari; Mehta, Goverdhan; Organic & biomolecular chemistry 23 (2025) 9100–9104; doi:10.1039/d5ob01279a

data_7160736
_publ_section_title
;
 Stitching ynones with indolin-2-thiones: an eco-friendly reaction cascade
 towards functionalized thiopyrano[2,3-<i>b</i>]indoles and their
 inceptive optoelectronic profiling.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; 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 H15 N S'
_chemical_formula_sum            'C23 H15 N S'
_chemical_formula_weight         337.448
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_audit_creation_date             2024-08-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-05-14 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.755(2)
_cell_length_b                   17.605(4)
_cell_length_c                   19.937(5)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.31
_cell_volume                     3423.9(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      102.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9922
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9922
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28725
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9922
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5471
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             1409.487
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.5856
_refine_diff_density_min         -0.3366
_refine_diff_density_rms         0.1079
_refine_ls_d_res_high            0.7660
_refine_ls_d_res_low             9.9684
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0124
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+1.1849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3262
_reflns_number_total             3962
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01279a2.cif
_cod_data_source_block           GM037_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160736--7160737.cif.'
_cod_original_cell_volume        3423.6(14)
_cod_database_code               7160736
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00P(H00P), C00O(H00O), C00N(H00N), C00L(H00L), C00E(H00E),
 C00G(H00G), C00I(H00I), C00B(H00B), C00H(H00H), C00K(H00K), C00J(H00J),
 C00F(H00F), C00C(H00C), C009(H009)
;
_olex2_submission_special_instructions 'No special instructions were received'