#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:24:36 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157807.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_7157807
loop_
_publ_author_name
'Kar, Abhishek'
'Chakraborty, Baitan'
'Kundal, Sandip'
'Rana, Gopal'
'Jana, Umasish'
_publ_section_title
;
 DDQ/FeCl₃-mediated tandem oxidative carbon-carbon bond
 formation for the Synthesis of indole-fluorene hybrid molecules.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              906
_journal_page_last               910
_journal_paper_doi               10.1039/d0ob00413h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C28 H21 N O2 S'
_chemical_formula_weight         435.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 104.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7300(20)
_cell_length_b                   20.980(4)
_cell_length_c                   11.450(2)
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      1.941
_cell_volume                     2264.0(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37120
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         1.941
_diffrn_source                   X-ray
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       'Rod Shaped'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.861
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1701
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2650
_reflns_number_total             5164
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00413h3.cif
_cod_data_source_block           UJ
_cod_depositor_comments          'Adding full bibliography for 7157807.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157807
_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.
;
_shelx_estimated_absorpt_t_min   0.6918
_shelx_estimated_absorpt_t_max   0.7456
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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 -0.00553(7) 0.11957(3) 0.10677(5) 0.0479(2) Uani 1 1 d . . . . .
N1 N 0.1055(2) 0.11584(9) 0.24190(17) 0.0415(5) Uani 1 1 d . . . . .
O1 O 0.0346(2) 0.07101(8) 0.03510(15) 0.0644(6) Uani 1 1 d . . . . .
C1 C -0.5590(4) 0.0528(2) 0.2221(4) 0.1278(16) Uani 1 1 d . . . . .
H1B H -0.584128 0.009640 0.197824 0.192 Uiso 1 1 calc R U . . .
H1C H -0.546756 0.056671 0.307566 0.192 Uiso 1 1 calc R U . . .
H1D H -0.633128 0.080962 0.181111 0.192 Uiso 1 1 calc R U . . .
O2 O -0.0057(2) 0.18484(8) 0.07207(14) 0.0592(5) Uani 1 1 d . . . . .
C2 C -0.4233(3) 0.06998(17) 0.1903(3) 0.0735(9) Uani 1 1 d . . . . .
C3 C -0.3529(4) 0.02549(15) 0.1367(3) 0.0777(9) Uani 1 1 d . . . . .
H3A H -0.391416 -0.015032 0.119712 0.093 Uiso 1 1 calc R U . . .
C4 C 0.5757(4) 0.13978(16) 0.7362(4) 0.0804(10) Uani 1 1 d . . . . .
H4A H 0.666685 0.128475 0.731828 0.096 Uiso 1 1 calc R U . . .
C5 C 0.5419(4) 0.13904(15) 0.8453(4) 0.0803(10) Uani 1 1 d . . . . .
H5A H 0.610850 0.127463 0.913948 0.096 Uiso 1 1 calc R U . . .
C6 C -0.1226(3) 0.22721(13) 0.6493(3) 0.0641(8) Uani 1 1 d . . . . .
H6A H -0.216906 0.239647 0.622097 0.077 Uiso 1 1 calc R U . . .
C7 C 0.1779(3) -0.02815(14) 0.4951(3) 0.0696(9) Uani 1 1 d . . . . .
H7A H 0.196296 -0.059037 0.555255 0.083 Uiso 1 1 calc R U . . .
C8 C -0.0657(4) 0.21714(14) 0.7702(3) 0.0709(9) Uani 1 1 d . . . . .
H8A H -0.122256 0.223014 0.823977 0.085 Uiso 1 1 calc R U . . .
C9 C 0.4764(3) 0.15708(13) 0.6327(3) 0.0646(8) Uani 1 1 d . . . . .
H9A H 0.499813 0.157748 0.558780 0.078 Uiso 1 1 calc R U . . .
C10 C -0.3626(3) 0.12983(15) 0.2154(3) 0.0684(9) Uani 1 1 d . . . . .
H10A H -0.408398 0.160240 0.251293 0.082 Uiso 1 1 calc R U . . .
C11 C 0.0734(4) 0.19853(13) 0.8135(2) 0.0610(8) Uani 1 1 d . . . . .
H11A H 0.110419 0.191164 0.895388 0.073 Uiso 1 1 calc R U . . .
C12 C -0.0399(3) 0.21888(12) 0.5677(2) 0.0546(7) Uani 1 1 d . . . . .
H12A H -0.078641 0.224780 0.485627 0.066 Uiso 1 1 calc R U . . .
C13 C -0.2272(3) 0.04005(13) 0.1082(3) 0.0592(7) Uani 1 1 d . . . . .
H13A H -0.181810 0.009813 0.071661 0.071 Uiso 1 1 calc R U . . .
C14 C 0.4081(4) 0.15507(13) 0.8556(3) 0.0675(9) Uani 1 1 d . . . . .
H14A H 0.385987 0.154265 0.930092 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1057(3) -0.00314(12) 0.2840(2) 0.0522(7) Uani 1 1 d . . . . .
H15A H 0.076252 -0.015807 0.203825 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3065(3) 0.17259(11) 0.7510(2) 0.0490(7) Uani 1 1 d . . . . .
C17 C 0.1314(3) -0.04678(13) 0.3760(3) 0.0630(8) Uani 1 1 d . . . . .
H17A H 0.117162 -0.089862 0.357936 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1977(3) 0.03514(14) 0.5267(3) 0.0615(8) Uani 1 1 d . . . . .
H18A H 0.228737 0.047098 0.607131 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1576(3) 0.19095(11) 0.7321(2) 0.0471(6) Uani 1 1 d . . . . .
C20 C -0.2372(3) 0.14532(13) 0.1888(2) 0.0540(7) Uani 1 1 d . . . . .
H20A H -0.197862 0.185628 0.206782 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1012(3) 0.20166(11) 0.6101(2) 0.0442(6) Uani 1 1 d . . . . .
C22 C -0.1693(3) 0.09999(12) 0.1344(2) 0.0449(6) Uani 1 1 d . . . . .
C23 C 0.3418(3) 0.17337(12) 0.6406(2) 0.0489(7) Uani 1 1 d . . . . .
C24 C 0.1254(2) 0.06059(12) 0.3154(2) 0.0420(6) Uani 1 1 d . . . . .
C25 C 0.1335(3) 0.16902(12) 0.3197(2) 0.0431(6) Uani 1 1 d . . . . .
H25A H 0.124430 0.211283 0.294389 0.052 Uiso 1 1 calc R U . . .
C26 C 0.1701(3) 0.08103(11) 0.4355(2) 0.0427(6) Uani 1 1 d . . . . .
C27 C 0.1748(3) 0.15030(11) 0.4345(2) 0.0418(6) Uani 1 1 d . . . . .
C28 C 0.2147(3) 0.19410(12) 0.5416(2) 0.0453(6) Uani 1 1 d . . . . .
H28A H 0.235100 0.236251 0.513059 0.054 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
O1 S1 O2 120.57(11) . . ?
O1 S1 N1 107.26(11) . . ?
O2 S1 N1 105.14(10) . . ?
O1 S1 C22 109.21(12) . . ?
O2 S1 C22 109.77(11) . . ?
N1 S1 C22 103.44(11) . . ?
C25 N1 C24 107.19(19) . . ?
C25 N1 S1 122.11(16) . . ?
C24 N1 S1 123.73(16) . . ?
C10 C2 C3 118.0(3) . . ?
C10 C2 C1 121.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C13 C3 C2 121.4(3) . . ?
C5 C4 C9 120.8(3) . . ?
C4 C5 C14 121.5(3) . . ?
C8 C6 C12 120.2(3) . . ?
C18 C7 C17 121.4(3) . . ?
C6 C8 C11 121.4(3) . . ?
C23 C9 C4 118.9(3) . . ?
C20 C10 C2 121.7(3) . . ?
C8 C11 C19 118.7(3) . . ?
C21 C12 C6 119.1(3) . . ?
C3 C13 C22 119.4(3) . . ?
C5 C14 C16 118.2(3) . . ?
C17 C15 C24 117.3(3) . . ?
C23 C16 C14 119.9(3) . . ?
C23 C16 C19 108.8(2) . . ?
C14 C16 C19 131.3(3) . . ?
C15 C17 C7 121.5(3) . . ?
C7 C18 C26 118.7(3) . . ?
C21 C19 C11 120.3(3) . . ?
C21 C19 C16 108.8(2) . . ?
C11 C19 C16 131.0(2) . . ?
C10 C20 C22 119.1(3) . . ?
C12 C21 C19 120.3(2) . . ?
C12 C21 C28 129.3(2) . . ?
C19 C21 C28 110.4(2) . . ?
C13 C22 C20 120.4(3) . . ?
C13 C22 S1 121.1(2) . . ?
C20 C22 S1 118.4(2) . . ?
C9 C23 C16 120.7(3) . . ?
C9 C23 C28 129.2(2) . . ?
C16 C23 C28 110.0(2) . . ?
C15 C24 C26 122.6(2) . . ?
C15 C24 N1 130.2(2) . . ?
C26 C24 N1 107.2(2) . . ?
C27 C25 N1 110.6(2) . . ?
C18 C26 C24 118.5(2) . . ?
C18 C26 C27 133.9(2) . . ?
C24 C26 C27 107.5(2) . . ?
C25 C27 C26 107.4(2) . . ?
C25 C27 C28 125.2(2) . . ?
C26 C27 C28 127.4(2) . . ?
C27 C28 C21 114.4(2) . . ?
C27 C28 C23 115.5(2) . . ?
C21 C28 C23 101.92(19) . . ?
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 O1 1.4222(17) . ?
S1 O2 1.4258(17) . ?
S1 N1 1.654(2) . ?
S1 C22 1.748(3) . ?
N1 C25 1.411(3) . ?
N1 C24 1.417(3) . ?
C1 C2 1.499(4) . ?
C2 C10 1.387(4) . ?
C2 C3 1.388(4) . ?
C3 C13 1.376(4) . ?
C4 C5 1.368(5) . ?
C4 C9 1.379(4) . ?
C5 C14 1.378(4) . ?
C6 C8 1.373(4) . ?
C6 C12 1.388(4) . ?
C7 C18 1.377(4) . ?
C7 C17 1.382(4) . ?
C8 C11 1.377(4) . ?
C9 C23 1.378(4) . ?
C10 C20 1.369(4) . ?
C11 C19 1.395(4) . ?
C12 C21 1.385(3) . ?
C13 C22 1.380(4) . ?
C14 C16 1.400(4) . ?
C15 C17 1.371(4) . ?
C15 C24 1.386(3) . ?
C16 C23 1.390(3) . ?
C16 C19 1.462(4) . ?
C18 C26 1.396(3) . ?
C19 C21 1.386(3) . ?
C20 C22 1.390(4) . ?
C21 C28 1.513(3) . ?
C23 C28 1.519(3) . ?
C24 C26 1.402(3) . ?
C25 C27 1.335(3) . ?
C26 C27 1.454(3) . ?
C27 C28 1.504(3) . ?
