The synthesis of indole-3-carbinols (I3C) and their application to access unsymmetrical bis(3-indolyl)methanes (BIMs) bearing a quaternary sp3-carbon
Kundal, Sandip; Rana, Gopal; Kar, Abhishek; Jana, Umasish; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00502F

data_7158733
_publ_section_title
;
 The synthesis of indole-3-carbinols (I3C) and their application to access
 unsymmetrical bis(3-indolyl)methanes (BIMs) bearing a quaternary
 sp3-carbon
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00502F
_journal_year                    2022
_chemical_formula_sum            'C27 H22 N2 O4 S'
_chemical_formula_weight         470.54
_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-2016/6
_audit_update_record
;
2022-03-05 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                104.028(3)
_cell_angle_beta                 95.447(3)
_cell_angle_gamma                108.651(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6868(10)
_cell_length_b                   11.8781(14)
_cell_length_c                   13.2771(15)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      1.8
_cell_volume                     1237.0(2)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31655
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.890
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.555
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.1134
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1555P)^2^+3.2245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3040
_refine_ls_wR_factor_ref         0.3264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3265
_reflns_number_total             4355
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00502f2.cif
_cod_data_source_block           UJ1
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         58.82
_cod_original_formula_units_Z            16
_cod_original_formula_sum        'C3.38 H2.75 N0.25 O0.50 S0.12'
_cod_database_code               7158733
_shelx_shelxl_version_number     2016/6
_exptl_absorpt_special_details
;
?
;
_shelx_res_checksum              9607