#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:49:12 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128949.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_7128949
loop_
_publ_author_name
'Wan, Jin-Lin'
'Cui, Jian-Feng'
'Zhong, Wei-Qiang'
'Huang, Jing-Mei'
_publ_section_title
;
 Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids:
 construction of indole-fused polycyclics.
;
_journal_issue                   79
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10242
_journal_page_last               10245
_journal_paper_doi               10.1039/d1cc03891e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C23 H18 N2 O2 S'
_chemical_formula_weight         386.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-04-29 deposited with the CCDC.	2021-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5865(2)
_cell_length_b                   14.3767(4)
_cell_length_c                   15.4328(3)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.978
_cell_measurement_theta_min      5.577
_cell_volume                     1881.80(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18815
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.788
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0407P)²+0.8117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3222
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03891e2.cif
_cod_data_source_block           mo_d8v21277_0m
_cod_depositor_comments          'Adding full bibliography for 7128949.cif.'
_cod_original_cell_volume        1881.79(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128949
_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   0.962
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_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 0.66356(4) 0.57348(3) 0.83136(3) 0.03485(12) Uani 1 1 d . . . . .
N1 N 0.61596(15) 0.57157(9) 0.71992(8) 0.0340(3) Uani 1 1 d . . . . .
N2 N 0.58911(19) 0.32627(10) 0.57099(10) 0.0473(4) Uani 1 1 d . . . . .
O1 O 0.80315(13) 0.51988(9) 0.85403(8) 0.0474(3) Uani 1 1 d . . . . .
O2 O 0.66248(13) 0.66904(8) 0.85520(8) 0.0461(3) Uani 1 1 d . . . . .
C1 C 0.46011(18) 0.60711(11) 0.68827(10) 0.0342(3) Uani 1 1 d . . . . .
C2 C 0.3925(2) 0.68919(12) 0.71143(11) 0.0423(4) Uani 1 1 d . . . . .
H2 H 0.4486 0.7304 0.7521 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2398(2) 0.70833(13) 0.67268(12) 0.0488(4) Uani 1 1 d . . . . .
H3 H 0.1906 0.7632 0.6876 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1582(2) 0.64760(14) 0.61197(13) 0.0523(5) Uani 1 1 d . . . . .
H4 H 0.0547 0.6623 0.5861 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2262(2) 0.56586(13) 0.58876(12) 0.0449(4) Uani 1 1 d . . . . .
H5 H 0.1701 0.5253 0.5474 0.054 Uiso 1 1 calc R U . . .
C6 C 0.37962(18) 0.54486(11) 0.62796(10) 0.0351(3) Uani 1 1 d . . . . .
C7 C 0.48684(18) 0.46784(11) 0.61966(10) 0.0339(3) Uani 1 1 d . . . . .
C8 C 0.62758(18) 0.48643(10) 0.67319(10) 0.0333(3) Uani 1 1 d . . . . .
C9 C 0.4708(2) 0.38485(12) 0.56886(11) 0.0406(4) Uani 1 1 d . . . . .
C10 C 0.7328(2) 0.34854(12) 0.61781(11) 0.0427(4) Uani 1 1 d . . . . .
C11 C 0.76334(19) 0.43072(11) 0.66971(10) 0.0375(4) Uani 1 1 d . . . . .
C12 C 0.9210(2) 0.45206(14) 0.70586(11) 0.0454(4) Uani 1 1 d . . . . .
H12 H 0.9445 0.5080 0.7367 0.055 Uiso 1 1 calc R U . . .
C13 C 1.0393(2) 0.39095(16) 0.69578(13) 0.0553(5) Uani 1 1 d . . . . .
H13 H 1.1438 0.4058 0.7196 0.066 Uiso 1 1 calc R U . . .
C14 C 1.0077(3) 0.30729(15) 0.65096(14) 0.0609(6) Uani 1 1 d . . . . .
H14 H 1.0897 0.2647 0.6478 0.073 Uiso 1 1 calc R U . . .
C15 C 0.8595(3) 0.28720(14) 0.61198(14) 0.0571(5) Uani 1 1 d . . . . .
H15 H 0.8402 0.2314 0.5804 0.069 Uiso 1 1 calc R U . . .
C16 C 0.3194(2) 0.36003(14) 0.51195(12) 0.0538(5) Uani 1 1 d . . . . .
H16A H 0.3280 0.2983 0.4877 0.081 Uiso 1 1 calc R U . . .
H16B H 0.2975 0.4048 0.4646 0.081 Uiso 1 1 calc R U . . .
H16C H 0.2344 0.3609 0.5466 0.081 Uiso 1 1 calc R U . . .
C17 C 0.50515(17) 0.51575(11) 0.86672(9) 0.0325(3) Uani 1 1 d . . . . .
C18 C 0.4973(2) 0.41994(12) 0.85968(11) 0.0414(4) Uani 1 1 d . . . . .
H18 H 0.5789 0.3864 0.8399 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3681(2) 0.37412(12) 0.88206(12) 0.0456(4) Uani 1 1 d . . . . .
H19 H 0.3616 0.3091 0.8764 0.055 Uiso 1 1 calc R U . . .
C20 C 0.24754(19) 0.42230(12) 0.91272(10) 0.0393(4) Uani 1 1 d . . . . .
C21 C 0.2603(2) 0.51811(12) 0.92081(12) 0.0438(4) Uani 1 1 d . . . . .
H21 H 0.1802 0.5515 0.9423 0.053 Uiso 1 1 calc R U . . .
C22 C 0.38774(19) 0.56586(11) 0.89803(11) 0.0396(4) Uani 1 1 d . . . . .
H22 H 0.3946 0.6309 0.9037 0.047 Uiso 1 1 calc R U . . .
C23 C 0.1056(2) 0.37189(14) 0.93552(13) 0.0527(5) Uani 1 1 d . . . . .
H23A H 0.1261 0.3526 0.9965 0.079 Uiso 1 1 calc R U . . .
H23B H 0.0844 0.3175 0.8983 0.079 Uiso 1 1 calc R U . . .
H23C H 0.0150 0.4130 0.9265 0.079 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 119.93(8) . . ?
O1 S1 N1 107.45(7) . . ?
O2 S1 N1 105.44(7) . . ?
O1 S1 C17 109.40(8) . . ?
O2 S1 C17 109.89(7) . . ?
N1 S1 C17 103.36(7) . . ?
C8 N1 C1 105.41(12) . . ?
C8 N1 S1 119.82(10) . . ?
C1 N1 S1 113.53(10) . . ?
C9 N2 C10 119.52(15) . . ?
C2 C1 C6 122.30(15) . . ?
C2 C1 N1 128.11(15) . . ?
C6 C1 N1 109.59(13) . . ?
C3 C2 C1 117.74(16) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 120.80(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.34(17) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.66(17) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.15(15) . . ?
C5 C6 C7 133.86(16) . . ?
C1 C6 C7 106.98(13) . . ?
C8 C7 C9 119.55(15) . . ?
C8 C7 C6 107.84(13) . . ?
C9 C7 C6 132.61(15) . . ?
C7 C8 C11 120.99(15) . . ?
C7 C8 N1 110.11(13) . . ?
C11 C8 N1 128.49(14) . . ?
N2 C9 C7 120.99(16) . . ?
N2 C9 C16 117.34(16) . . ?
C7 C9 C16 121.67(16) . . ?
N2 C10 C15 117.39(17) . . ?
N2 C10 C11 124.18(15) . . ?
C15 C10 C11 118.40(18) . . ?
C12 C11 C8 127.04(16) . . ?
C12 C11 C10 118.75(15) . . ?
C8 C11 C10 114.02(15) . . ?
C13 C12 C11 119.78(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.32(19) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 120.18(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 121.07(15) . . ?
C18 C17 S1 118.58(12) . . ?
C22 C17 S1 120.31(12) . . ?
C19 C18 C17 119.18(16) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.23(16) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 118.29(16) . . ?
C21 C20 C23 120.83(17) . . ?
C19 C20 C23 120.88(16) . . ?
C22 C21 C20 121.66(16) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 118.56(15) . . ?
C21 C22 H22 120.7 . . ?
C17 C22 H22 120.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 1.4220(12) . ?
S1 O2 1.4227(12) . ?
S1 N1 1.7047(13) . ?
S1 C17 1.7517(15) . ?
N1 C8 1.432(2) . ?
N1 C1 1.4445(19) . ?
N2 C9 1.316(2) . ?
N2 C10 1.367(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.458(2) . ?
C7 C8 1.380(2) . ?
C7 C9 1.422(2) . ?
C8 C11 1.422(2) . ?
C9 C16 1.494(2) . ?
C10 C15 1.414(2) . ?
C10 C11 1.428(2) . ?
C11 C12 1.415(2) . ?
C12 C13 1.370(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.351(3) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.383(2) . ?
C17 C22 1.386(2) . ?
C18 C19 1.379(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9400 . ?
C20 C21 1.386(2) . ?
C20 C23 1.506(2) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.94 2.40 2.963(2) 118.1 .
C2 H2 O2 0.94 2.40 2.963(2) 118.1 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 42.46(13) . . . . ?
O2 S1 N1 C8 171.46(11) . . . . ?
C17 S1 N1 C8 -73.17(12) . . . . ?
O1 S1 N1 C1 168.16(11) . . . . ?
O2 S1 N1 C1 -62.84(11) . . . . ?
C17 S1 N1 C1 52.53(12) . . . . ?
C8 N1 C1 C2 -178.23(15) . . . . ?
S1 N1 C1 C2 48.73(19) . . . . ?
C8 N1 C1 C6 2.12(16) . . . . ?
S1 N1 C1 C6 -130.92(11) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C2 C3 -179.46(15) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 -179.49(17) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
N1 C1 C6 C5 -179.76(13) . . . . ?
C2 C1 C6 C7 179.61(14) . . . . ?
N1 C1 C6 C7 -0.72(16) . . . . ?
C5 C6 C7 C8 177.80(17) . . . . ?
C1 C6 C7 C8 -1.04(16) . . . . ?
C5 C6 C7 C9 -1.4(3) . . . . ?
C1 C6 C7 C9 179.77(16) . . . . ?
C9 C7 C8 C11 8.5(2) . . . . ?
C6 C7 C8 C11 -170.79(13) . . . . ?
C9 C7 C8 N1 -178.26(13) . . . . ?
C6 C7 C8 N1 2.42(16) . . . . ?
C1 N1 C8 C7 -2.80(16) . . . . ?
S1 N1 C8 C7 126.63(12) . . . . ?
C1 N1 C8 C11 169.75(14) . . . . ?
S1 N1 C8 C11 -60.81(19) . . . . ?
C10 N2 C9 C7 -4.7(2) . . . . ?
C10 N2 C9 C16 176.02(15) . . . . ?
C8 C7 C9 N2 -1.2(2) . . . . ?
C6 C7 C9 N2 177.93(15) . . . . ?
C8 C7 C9 C16 178.11(15) . . . . ?
C6 C7 C9 C16 -2.8(3) . . . . ?
C9 N2 C10 C15 -174.68(15) . . . . ?
C9 N2 C10 C11 3.4(2) . . . . ?
C7 C8 C11 C12 165.61(15) . . . . ?
N1 C8 C11 C12 -6.2(3) . . . . ?
C7 C8 C11 C10 -9.3(2) . . . . ?
N1 C8 C11 C10 178.85(14) . . . . ?
N2 C10 C11 C12 -171.85(15) . . . . ?
C15 C10 C11 C12 6.2(2) . . . . ?
N2 C10 C11 C8 3.5(2) . . . . ?
C15 C10 C11 C8 -178.43(14) . . . . ?
C8 C11 C12 C13 -179.23(16) . . . . ?
C10 C11 C12 C13 -4.5(2) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 3.8(3) . . . . ?
C13 C14 C15 C10 -2.0(3) . . . . ?
N2 C10 C15 C14 175.17(17) . . . . ?
C11 C10 C15 C14 -3.0(3) . . . . ?
O1 S1 C17 C18 -38.25(15) . . . . ?
O2 S1 C17 C18 -171.87(13) . . . . ?
N1 S1 C17 C18 75.98(14) . . . . ?
O1 S1 C17 C22 144.06(13) . . . . ?
O2 S1 C17 C22 10.43(15) . . . . ?
N1 S1 C17 C22 -101.71(13) . . . . ?
C22 C17 C18 C19 1.8(2) . . . . ?
S1 C17 C18 C19 -175.92(13) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C18 C19 C20 C23 178.94(16) . . . . ?
C19 C20 C21 C22 0.9(3) . . . . ?
C23 C20 C21 C22 -178.30(16) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C18 C17 C22 C21 -1.1(2) . . . . ?
S1 C17 C22 C21 176.50(13) . . . . ?
