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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/86/7108631.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_7108631
loop_
_publ_author_name
'Min Yang'
'Jie Tang'
'Renhua Fan'
_publ_section_title
;
 Accessing N-heteroarylated indoles and benzimidazoles from 2-alkynyl
 cyclohexadienimines and cyclohexadienones through metal-catalyzed tandem
 reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              11775
_journal_paper_doi               10.1039/c2cc36113b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C39 H35 N2 O2 S'
_chemical_formula_weight         595.75
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.619(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.111(13)
_cell_length_b                   9.641(7)
_cell_length_c                   20.781(16)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.552
_cell_measurement_theta_min      2.860
_cell_volume                     3380(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14014
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1036P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                4212
_reflns_number_total             6242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36113b.txt
_cod_data_source_block           a20221b
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7108631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.16039(3) 0.50759(6) 1.05117(3) 0.04061(19) Uani 1 1 d .
O1 O 0.21543(11) 0.45105(18) 1.10389(8) 0.0537(5) Uani 1 1 d .
O2 O 0.08366(10) 0.44670(17) 1.03315(8) 0.0509(4) Uani 1 1 d .
N1 N 0.20301(11) 0.49884(17) 0.98310(9) 0.0382(4) Uani 1 1 d .
N2 N 0.25707(12) 0.7450(2) 0.79878(9) 0.0457(5) Uani 1 1 d .
C1 C 0.14963(15) 0.6871(2) 1.06431(11) 0.0427(6) Uani 1 1 d .
C2 C 0.21701(17) 0.7640(3) 1.09038(13) 0.0579(7) Uani 1 1 d .
H2 H 0.2666 0.7222 1.0992 0.069 Uiso 1 1 calc R
C3 C 0.2080(2) 0.9040(3) 1.10267(15) 0.0730(9) Uani 1 1 d .
H3 H 0.2524 0.9562 1.1194 0.088 Uiso 1 1 calc R
C4 C 0.1346(2) 0.9682(3) 1.09074(14) 0.0697(9) Uani 1 1 d .
C5 C 0.0684(2) 0.8892(3) 1.06462(14) 0.0675(8) Uani 1 1 d .
H5 H 0.0188 0.9309 1.0564 0.081 Uiso 1 1 calc R
C6 C 0.07555(16) 0.7495(3) 1.05082(12) 0.0526(6) Uani 1 1 d .
H6 H 0.0313 0.6982 1.0327 0.063 Uiso 1 1 calc R
C7 C 0.1249(3) 1.1218(3) 1.1065(2) 0.1166(16) Uani 1 1 d .
H7A H 0.1758 1.1605 1.1239 0.175 Uiso 1 1 calc R
H7B H 0.0902 1.1307 1.1380 0.175 Uiso 1 1 calc R
H7C H 0.1028 1.1705 1.0673 0.175 Uiso 1 1 calc R
C8 C 0.34111(18) 0.3162(3) 1.05178(13) 0.0585(7) Uani 1 1 d .
H8 H 0.2961 0.2660 1.0344 0.070 Uiso 1 1 calc R
C9 C 0.4008(2) 0.2530(4) 1.09517(15) 0.0751(9) Uani 1 1 d .
H9 H 0.3954 0.1611 1.1072 0.090 Uiso 1 1 calc R
C10 C 0.4686(2) 0.3271(5) 1.12074(16) 0.0892(12) Uani 1 1 d .
H10 H 0.5084 0.2848 1.1502 0.107 Uiso 1 1 calc R
C11 C 0.47693(19) 0.4636(4) 1.10251(16) 0.0812(10) Uani 1 1 d .
H11 H 0.5226 0.5127 1.1193 0.097 Uiso 1 1 calc R
C12 C 0.41701(17) 0.5273(3) 1.05912(14) 0.0619(7) Uani 1 1 d .
H12 H 0.4229 0.6190 1.0469 0.074 Uiso 1 1 calc R
C13 C 0.34810(15) 0.4550(3) 1.03383(11) 0.0454(6) Uani 1 1 d .
C14 C 0.28655(13) 0.5212(2) 0.98481(10) 0.0391(5) Uani 1 1 d .
C15 C 0.29663(14) 0.5934(2) 0.93045(11) 0.0438(6) Uani 1 1 d .
H15 H 0.3451 0.6212 0.9201 0.053 Uiso 1 1 calc R
C16 C 0.21995(13) 0.6199(2) 0.89151(10) 0.0384(5) Uani 1 1 d .
C17 C 0.16250(13) 0.5628(2) 0.92456(10) 0.0375(5) Uani 1 1 d .
C18 C 0.08225(14) 0.5729(2) 0.89953(12) 0.0456(6) Uani 1 1 d .
H18 H 0.0442 0.5380 0.9223 0.055 Uiso 1 1 calc R
C19 C 0.06067(15) 0.6371(3) 0.83921(12) 0.0502(6) Uani 1 1 d .
H19 H 0.0071 0.6432 0.8218 0.060 Uiso 1 1 calc R
C20 C 0.11612(15) 0.6933(3) 0.80319(11) 0.0474(6) Uani 1 1 d .
C21 C 0.19657(14) 0.6855(2) 0.83083(11) 0.0415(5) Uani 1 1 d .
C22 C 0.08798(18) 0.7605(3) 0.73735(13) 0.0678(8) Uani 1 1 d .
H22A H 0.0735 0.8551 0.7436 0.102 Uiso 1 1 calc R
H22B H 0.0428 0.7110 0.7150 0.102 Uiso 1 1 calc R
H22C H 0.1298 0.7578 0.7118 0.102 Uiso 1 1 calc R
C23 C 0.31146(14) 0.6671(3) 0.77070(11) 0.0458(6) Uani 1 1 d .
C24 C 0.32351(16) 0.5237(3) 0.77082(12) 0.0526(6) Uani 1 1 d .
H24 H 0.2925 0.4638 0.7910 0.063 Uiso 1 1 calc R
C25 C 0.38350(18) 0.4742(3) 0.73964(13) 0.0633(8) Uani 1 1 d .
H25 H 0.3932 0.3793 0.7391 0.076 Uiso 1 1 calc R
C26 C 0.42992(18) 0.5647(4) 0.70882(14) 0.0683(8) Uani 1 1 d .
H26 H 0.4701 0.5288 0.6887 0.082 Uiso 1 1 calc R
C27 C 0.41690(17) 0.7059(3) 0.70791(13) 0.0631(8) Uani 1 1 d .
H27 H 0.4474 0.7645 0.6866 0.076 Uiso 1 1 calc R
C28 C 0.35703(15) 0.7606(3) 0.73955(11) 0.0509(6) Uani 1 1 d .
C29 C 0.32712(16) 0.8966(3) 0.74905(12) 0.0560(7) Uani 1 1 d .
H29 H 0.3451 0.9787 0.7331 0.067 Uiso 1 1 calc R
C30 C 0.26795(15) 0.8858(3) 0.78532(12) 0.0493(6) Uani 1 1 d .
C31 C 0.22157(16) 0.9963(3) 0.81118(13) 0.0542(6) Uani 1 1 d .
C32 C 0.1966(2) 1.1132(3) 0.77311(16) 0.0715(8) Uani 1 1 d .
H32 H 0.2074 1.1193 0.7308 0.086 Uiso 1 1 calc R
C33 C 0.1559(2) 1.2200(3) 0.7980(2) 0.0874(10) Uani 1 1 d .
H33 H 0.1401 1.2972 0.7723 0.105 Uiso 1 1 calc R
C34 C 0.1386(2) 1.2128(4) 0.8598(2) 0.0929(12) Uani 1 1 d .
H34 H 0.1109 1.2843 0.8759 0.111 Uiso 1 1 calc R
C35 C 0.1628(2) 1.0983(4) 0.89846(18) 0.0827(10) Uani 1 1 d .
H35 H 0.1513 1.0933 0.9406 0.099 Uiso 1 1 calc R
C36 C 0.20403(18) 0.9910(3) 0.87474(15) 0.0642(8) Uani 1 1 d .
H36 H 0.2202 0.9150 0.9012 0.077 Uiso 1 1 calc R
C37 C 0.4919(2) 0.0613(4) 0.97694(18) 0.0938(11) Uani 1 1 d .
H37A H 0.4982 0.1457 1.0027 0.113 Uiso 1 1 calc R
H37B H 0.5320 0.0622 0.9490 0.113 Uiso 1 1 calc R
C38 C 0.4122(3) 0.0644(5) 0.9346(2) 0.1054(13) Uani 1 1 d .
H38A H 0.3719 0.0559 0.9621 0.126 Uiso 1 1 calc R
H38B H 0.4075 -0.0155 0.9058 0.126 Uiso 1 1 calc R
C39 C 0.3959(2) 0.1946(4) 0.8933(2) 0.0971(12) Uani 1 1 d .
H39A H 0.4113 0.2747 0.9199 0.146 Uiso 1 1 calc R
H39B H 0.3403 0.1999 0.8759 0.146 Uiso 1 1 calc R
H39C H 0.4257 0.1915 0.8581 0.146 Uiso 1 1 calc R
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
O1 S1 O2 120.21(11) . .
O1 S1 N1 107.46(11) . .
O2 S1 N1 105.35(10) . .
O1 S1 C1 109.14(12) . .
O2 S1 C1 109.14(12) . .
N1 S1 C1 104.34(9) . .
C17 N1 C14 107.07(16) . .
C17 N1 S1 118.10(15) . .
C14 N1 S1 122.31(15) . .
C23 N2 C30 108.46(19) . .
C23 N2 C21 124.00(19) . .
C30 N2 C21 127.34(19) . .
C6 C1 C2 120.9(2) . .
C6 C1 S1 120.6(2) . .
C2 C1 S1 118.5(2) . .
C3 C2 C1 118.4(3) . .
C3 C2 H2 120.8 . .
C1 C2 H2 120.8 . .
C4 C3 C2 121.8(3) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 118.6(3) . .
C3 C4 C7 121.4(3) . .
C5 C4 C7 120.1(3) . .
C6 C5 C4 121.1(3) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C1 119.2(3) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C13 120.5(3) . .
C9 C8 H8 119.8 . .
C13 C8 H8 119.8 . .
C8 C9 C10 120.0(3) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C9 120.1(3) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C12 120.0(3) . .
C10 C11 H11 120.0 . .
C12 C11 H11 120.0 . .
C11 C12 C13 120.6(3) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C12 C13 C8 118.8(3) . .
C12 C13 C14 120.2(2) . .
C8 C13 C14 120.8(2) . .
C15 C14 N1 108.6(2) . .
C15 C14 C13 128.0(2) . .
N1 C14 C13 122.76(19) . .
C14 C15 C16 109.0(2) . .
C14 C15 H15 125.5 . .
C16 C15 H15 125.5 . .
C17 C16 C21 119.8(2) . .
C17 C16 C15 107.6(2) . .
C21 C16 C15 132.6(2) . .
C18 C17 C16 121.3(2) . .
C18 C17 N1 131.0(2) . .
C16 C17 N1 107.76(19) . .
C17 C18 C19 117.8(2) . .
C17 C18 H18 121.1 . .
C19 C18 H18 121.1 . .
C18 C19 C20 123.2(2) . .
C18 C19 H19 118.4 . .
C20 C19 H19 118.4 . .
C21 C20 C19 117.6(2) . .
C21 C20 C22 122.3(2) . .
C19 C20 C22 120.1(2) . .
C20 C21 C16 120.3(2) . .
C20 C21 N2 121.4(2) . .
C16 C21 N2 118.3(2) . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N2 C23 C24 129.7(2) . .
N2 C23 C28 107.7(2) . .
C24 C23 C28 122.5(2) . .
C25 C24 C23 117.4(2) . .
C25 C24 H24 121.3 . .
C23 C24 H24 121.3 . .
C24 C25 C26 121.2(3) . .
C24 C25 H25 119.4 . .
C26 C25 H25 119.4 . .
C27 C26 C25 121.1(3) . .
C27 C26 H26 119.4 . .
C25 C26 H26 119.4 . .
C26 C27 C28 119.5(3) . .
C26 C27 H27 120.3 . .
C28 C27 H27 120.3 . .
C27 C28 C23 118.3(2) . .
C27 C28 C29 135.3(2) . .
C23 C28 C29 106.4(2) . .
C30 C29 C28 108.7(2) . .
C30 C29 H29 125.6 . .
C28 C29 H29 125.6 . .
C29 C30 N2 108.6(2) . .
C29 C30 C31 129.6(2) . .
N2 C30 C31 121.7(2) . .
C32 C31 C36 117.9(3) . .
C32 C31 C30 120.3(2) . .
C36 C31 C30 121.8(2) . .
C33 C32 C31 120.6(3) . .
C33 C32 H32 119.7 . .
C31 C32 H32 119.7 . .
C34 C33 C32 120.8(3) . .
C34 C33 H33 119.6 . .
C32 C33 H33 119.6 . .
C33 C34 C35 119.6(3) . .
C33 C34 H34 120.2 . .
C35 C34 H34 120.2 . .
C34 C35 C36 120.5(3) . .
C34 C35 H35 119.7 . .
C36 C35 H35 119.7 . .
C35 C36 C31 120.6(3) . .
C35 C36 H36 119.7 . .
C31 C36 H36 119.7 . .
C38 C37 C37 116.0(4) . 3_657
C38 C37 H37A 108.3 . .
C37 C37 H37A 108.3 3_657 .
C38 C37 H37B 108.3 . .
C37 C37 H37B 108.3 3_657 .
H37A C37 H37B 107.4 . .
C37 C38 C39 114.3(4) . .
C37 C38 H38A 108.7 . .
C39 C38 H38A 108.7 . .
C37 C38 H38B 108.7 . .
C39 C38 H38B 108.7 . .
H38A C38 H38B 107.6 . .
C38 C39 H39A 109.5 . .
C38 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
C38 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4281(19) .
S1 O2 1.430(2) .
S1 N1 1.699(2) .
S1 C1 1.767(3) .
N1 C17 1.435(3) .
N1 C14 1.440(3) .
N2 C23 1.397(3) .
N2 C30 1.405(3) .
N2 C21 1.441(3) .
C1 C6 1.388(4) .
C1 C2 1.401(4) .
C2 C3 1.387(4) .
C2 H2 0.9300 .
C3 C4 1.384(5) .
C3 H3 0.9300 .
C4 C5 1.397(5) .
C4 C7 1.532(4) .
C5 C6 1.386(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C9 1.385(4) .
C8 C13 1.400(4) .
C8 H8 0.9300 .
C9 C10 1.391(5) .
C9 H9 0.9300 .
C10 C11 1.383(5) .
C10 H10 0.9300 .
C11 C12 1.390(4) .
C11 H11 0.9300 .
C12 C13 1.395(4) .
C12 H12 0.9300 .
C13 C14 1.482(3) .
C14 C15 1.363(3) .
C15 C16 1.445(3) .
C15 H15 0.9300 .
C16 C17 1.402(3) .
C16 C21 1.407(3) .
C17 C18 1.388(3) .
C18 C19 1.391(4) .
C18 H18 0.9300 .
C19 C20 1.411(3) .
C19 H19 0.9300 .
C20 C21 1.402(4) .
C20 C22 1.518(4) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 C24 1.398(4) .
C23 C28 1.417(3) .
C24 C25 1.387(4) .
C24 H24 0.9300 .
C25 C26 1.405(4) .
C25 H25 0.9300 .
C26 C27 1.379(4) .
C26 H26 0.9300 .
C27 C28 1.409(4) .
C27 H27 0.9300 .
C28 C29 1.433(4) .
C29 C30 1.364(3) .
C29 H29 0.9300 .
C30 C31 1.482(4) .
C31 C32 1.402(4) .
C31 C36 1.403(4) .
C32 C33 1.391(4) .
C32 H32 0.9300 .
C33 C34 1.367(5) .
C33 H33 0.9300 .
C34 C35 1.387(5) .
C34 H34 0.9300 .
C35 C36 1.388(4) .
C35 H35 0.9300 .
C36 H36 0.9300 .
C37 C38 1.496(6) .
C37 C37 1.518(8) 3_657
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C38 C39 1.519(6) .
C38 H38A 0.9700 .
C38 H38B 0.9700 .
C39 H39A 0.9600 .
C39 H39B 0.9600 .
C39 H39C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182885
