#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158733.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_7158733
loop_
_publ_author_name
'Kundal, Sandip'
'Rana, Gopal'
'Kar, Abhishek'
'Jana, Umasish'
_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 & 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/[σ²(Fo²)+(0.1555P)²+3.2245P] where P=(Fo²+2Fc²)/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 > 2σ(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
_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.
;
_exptl_absorpt_special_details
;
?
;
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
S1 S 0.77402(18) 0.95002(14) 0.72353(11) 0.0377(5) Uani 1 1 d . . . . .
O3 O 0.8263(5) 0.7331(4) 0.2646(3) 0.0436(11) Uani 1 1 d . . . . .
H3 H 0.818972 0.800761 0.267093 0.065 Uiso 1 1 calc R U . . .
O2 O 0.8825(6) 1.0752(4) 0.7687(4) 0.0515(12) Uani 1 1 d . . . . .
O1 O 0.5995(5) 0.9195(5) 0.6953(4) 0.0539(12) Uani 1 1 d . . . . .
N1 N 0.8312(6) 0.8955(4) 0.6097(4) 0.0356(11) Uani 1 1 d . . . . .
N2 N 1.1300(6) 0.9787(5) 0.6611(4) 0.0393(12) Uani 1 1 d . . . . .
C7 C 0.8009(7) 0.7666(5) 0.4459(4) 0.0329(12) Uani 1 1 d . . . . .
C3 C 0.9765(6) 0.8286(5) 0.4923(4) 0.0297(12) Uani 1 1 d . . . . .
C1 C 0.7196(7) 0.8089(5) 0.5203(4) 0.0363(13) Uani 1 1 d . . . . .
H1 H 0.605153 0.783610 0.512843 0.044 Uiso 1 1 calc R U . . .
C2 C 0.9910(6) 0.9054(5) 0.5924(4) 0.0312(12) Uani 1 1 d . . . . .
C8 C 0.7330(7) 0.6809(5) 0.3361(4) 0.0341(13) Uani 1 1 d . . . . .
C15 C 0.7581(7) 0.5571(5) 0.3249(5) 0.0364(13) Uani 1 1 d . . . . .
C00D C 0.8113(7) 0.8595(5) 0.8032(4) 0.0367(13) Uani 1 1 d . . . . .
C5 C 1.2688(7) 0.8984(6) 0.5276(6) 0.0453(15) Uani 1 1 d . . . . .
H5 H 1.368909 0.897565 0.508633 0.054 Uiso 1 1 calc R U . . .
C6 C 1.2672(8) 0.9714(6) 0.6258(6) 0.0476(16) Uani 1 1 d . . . . .
H6 H 1.368488 1.018871 0.670461 0.057 Uiso 1 1 calc R U . . .
C4 C 1.1240(7) 0.8275(5) 0.4585(5) 0.0409(14) Uani 1 1 d . . . . .
H4 H 1.123350 0.780065 0.391416 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5491(8) 0.6579(5) 0.3028(5) 0.0408(14) Uani 1 1 d . . . . .
O1W O 0.5516(10) 0.9207(7) 0.0473(6) 0.118(3) Uani 1 1 d . . . . .
C00J C 0.8710(11) 0.7226(7) 0.9346(5) 0.0586(19) Uani 1 1 d . . . . .
C10 C 0.4288(8) 0.5864(7) 0.3463(6) 0.0575(18) Uani 1 1 d . . . . .
H10 H 0.460647 0.551453 0.396511 0.069 Uiso 1 1 calc R U . . .
C00L C 0.9640(9) 0.8993(7) 0.8686(5) 0.0520(17) Uani 1 1 d . . . . .
H00L H 1.047098 0.972128 0.869227 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4980(9) 0.7068(7) 0.2278(6) 0.0610(19) Uani 1 1 d . . . . .
H14 H 0.576041 0.753172 0.196315 0.073 Uiso 1 1 calc R U . . .
C00N C 0.9910(10) 0.8292(7) 0.9328(6) 0.0607(19) Uani 1 1 d . . . . .
H00N H 1.093949 0.855379 0.976087 0.073 Uiso 1 1 calc R U . . .
C20 C 0.7525(9) 0.4839(6) 0.2251(6) 0.0533(17) Uani 1 1 d . . . . .
H20 H 0.734834 0.511030 0.166449 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7804(10) 0.5123(6) 0.4100(6) 0.0602(19) Uani 1 1 d . . . . .
H16 H 0.782905 0.559164 0.477758 0.072 Uiso 1 1 calc R U . . .
C00Q C 0.6871(9) 0.7521(7) 0.8022(6) 0.0585(19) Uani 1 1 d . . . . .
H00Q H 0.584769 0.725002 0.757976 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7731(11) 0.3694(7) 0.2120(7) 0.071(2) Uani 1 1 d . . . . .
H19 H 0.771599 0.322089 0.144613 0.086 Uiso 1 1 calc R U . . .
C00S C 0.7188(11) 0.6858(7) 0.8688(6) 0.067(2) Uani 1 1 d . . . . .
H00S H 0.635284 0.613907 0.869657 0.080 Uiso 1 1 calc R U . . .
C11 C 0.2625(10) 0.5659(9) 0.3168(7) 0.076(3) Uani 1 1 d . . . . .
H11 H 0.183787 0.518077 0.346964 0.091 Uiso 1 1 calc R U . . .
C00U C 0.8992(14) 0.6475(8) 1.0071(7) 0.088(3) Uani 1 1 d . . . . .
H00A H 0.800987 0.576363 0.996853 0.133 Uiso 1 1 calc R U . . .
H00B H 0.989597 0.620662 0.991240 0.133 Uiso 1 1 calc R U . . .
H00C H 0.924956 0.697922 1.079264 0.133 Uiso 1 1 calc R U . . .
C18 C 0.7951(11) 0.3266(7) 0.2956(8) 0.076(3) Uani 1 1 d . . . . .
H18 H 0.807480 0.250004 0.285855 0.092 Uiso 1 1 calc R U . . .
C13 C 0.2153(10) 0.6170(9) 0.2424(8) 0.081(3) Uani 1 1 d . . . . .
H13 H 0.103838 0.603225 0.221924 0.097 Uiso 1 1 calc R U . . .
C12 C 0.3306(11) 0.6881(9) 0.1979(8) 0.082(3) Uani 1 1 d . . . . .
H12 H 0.298068 0.723511 0.148375 0.099 Uiso 1 1 calc R U . . .
C17 C 0.7991(12) 0.3970(8) 0.3947(8) 0.082(3) Uani 1 1 d . . . . .
H17 H 0.814432 0.367896 0.452555 0.098 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 121.2(3) . . ?
O2 S1 N1 106.9(3) . . ?
O1 S1 N1 104.4(2) . . ?
O2 S1 C00D 109.3(3) . . ?
O1 S1 C00D 109.1(3) . . ?
N1 S1 C00D 104.4(2) . . ?
C1 N1 C2 107.5(5) . . ?
C1 N1 S1 123.4(4) . . ?
C2 N1 S1 127.9(4) . . ?
C2 N2 C6 113.2(5) . . ?
C1 C7 C3 105.5(5) . . ?
C1 C7 C8 129.4(5) . . ?
C3 C7 C8 125.0(5) . . ?
C2 C3 C4 116.7(5) . . ?
C2 C3 C7 108.3(5) . . ?
C4 C3 C7 135.0(5) . . ?
C7 C1 N1 110.9(5) . . ?
N2 C2 C3 127.5(5) . . ?
N2 C2 N1 124.7(5) . . ?
C3 C2 N1 107.7(5) . . ?
O3 C8 C7 109.0(4) . . ?
O3 C8 C15 104.3(4) . . ?
C7 C8 C15 111.7(5) . . ?
O3 C8 C9 110.3(5) . . ?
C7 C8 C9 111.5(4) . . ?
C15 C8 C9 109.8(5) . . ?
C16 C15 C20 118.1(6) . . ?
C16 C15 C8 122.8(5) . . ?
C20 C15 C8 119.0(5) . . ?
C00Q C00D C00L 120.9(6) . . ?
C00Q C00D S1 119.8(5) . . ?
C00L C00D S1 119.3(5) . . ?
C4 C5 C6 120.2(6) . . ?
N2 C6 C5 124.6(6) . . ?
C5 C4 C3 117.7(6) . . ?
C14 C9 C10 117.9(6) . . ?
C14 C9 C8 120.7(6) . . ?
C10 C9 C8 121.4(6) . . ?
C00N C00J C00S 117.7(7) . . ?
C00N C00J C00U 121.9(8) . . ?
C00S C00J C00U 120.4(7) . . ?
C11 C10 C9 121.6(8) . . ?
C00N C00L C00D 119.0(7) . . ?
C9 C14 C12 121.3(8) . . ?
C00J C00N C00L 121.9(7) . . ?
C15 C20 C19 120.5(7) . . ?
C15 C16 C17 120.4(7) . . ?
C00D C00Q C00S 118.2(7) . . ?
C18 C19 C20 121.0(8) . . ?
C00Q C00S C00J 122.3(7) . . ?
C13 C11 C10 119.2(8) . . ?
C19 C18 C17 119.4(7) . . ?
C12 C13 C11 120.7(8) . . ?
C13 C12 C14 119.3(9) . . ?
C18 C17 C16 120.6(8) . . ?
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
S1 O2 1.422(5) . ?
S1 O1 1.430(4) . ?
S1 N1 1.681(5) . ?
S1 C00D 1.757(6) . ?
O3 C8 1.432(7) . ?
N1 C1 1.399(7) . ?
N1 C2 1.402(7) . ?
N2 C2 1.335(7) . ?
N2 C6 1.342(8) . ?
C7 C1 1.359(8) . ?
C7 C3 1.460(8) . ?
C7 C8 1.498(8) . ?
C3 C2 1.386(8) . ?
C3 C4 1.401(8) . ?
C8 C15 1.529(8) . ?
C8 C9 1.533(8) . ?
C15 C16 1.383(9) . ?
C15 C20 1.383(9) . ?
C00D C00Q 1.379(9) . ?
C00D C00L 1.385(9) . ?
C5 C4 1.364(9) . ?
C5 C6 1.384(9) . ?
C9 C14 1.373(9) . ?
C9 C10 1.390(9) . ?
C00J C00N 1.366(11) . ?
C00J C00S 1.388(11) . ?
C00J C00U 1.515(10) . ?
C10 C11 1.386(10) . ?
C00L C00N 1.380(10) . ?
C14 C12 1.401(11) . ?
C20 C19 1.400(10) . ?
C16 C17 1.400(10) . ?
C00Q C00S 1.382(10) . ?
C19 C18 1.350(12) . ?
C11 C13 1.373(13) . ?
C18 C17 1.369(13) . ?
C13 C12 1.370(14) . ?
