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#$Date: 2024-02-04 13:01:41 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132363.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_7132363
loop_
_publ_author_name
'He, Jiwen'
'Li, Xiaohua'
'He, Qiuqin'
'Fan, Renhua'
_publ_section_title
;
 Cascade alkyl migration in 2-alkynylanilines for the synthesis of
 benzenoid ring multi-functionalized indoles.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              71
_journal_page_last               74
_journal_paper_doi               10.1039/d3cc04815b
_journal_volume                  60
_journal_year                    2023
_chemical_formula_sum            'C27.5 H28 Cl N O3 S'
_chemical_formula_weight         488.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.401(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9459(9)
_cell_length_b                   9.6231(4)
_cell_length_c                   28.0552(13)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      56.94
_cell_measurement_theta_min      3.31
_cell_volume                     4880.9(4)
_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-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24580
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.959
_diffrn_reflns_theta_min         4.528
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       sheet
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0508P)²+5.9890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4418
_reflns_number_total             4953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04815b2.cif
_cod_data_source_block           ga_221026b_a
_cod_depositor_comments
'Adding full bibliography for 7132361--7132365.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C27.50 H28 Cl N O3 S'
_cod_database_code               7132363
_shelx_shelxl_version_number     2019/2
_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   0.741
_shelx_estimated_absorpt_t_max   0.939
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.18569(2) 0.62959(4) 0.58168(2) 0.02371(12) Uani 1 1 d . . . . .
O1 O 0.23461(6) 0.73884(12) 0.57769(4) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.12685(6) 0.65821(12) 0.60239(4) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.09436(7) 0.05564(12) 0.67096(5) 0.0377(3) Uani 1 1 d . . . . .
N1 N 0.23909(7) 0.50213(14) 0.61773(5) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.28082(9) 0.42594(18) 0.59050(6) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.26155(9) 0.29050(18) 0.58776(6) 0.0294(4) Uani 1 1 d . . . . .
H2 H 0.280110 0.220347 0.570906 0.035 Uiso 1 1 calc R U . . .
C3 C 0.20811(9) 0.26937(17) 0.61460(6) 0.0266(3) Uani 1 1 d . . . . .
C4 C 0.17377(9) 0.15041(17) 0.62548(6) 0.0298(4) Uani 1 1 d . . . . .
H4 H 0.179925 0.062672 0.611715 0.036 Uiso 1 1 calc R U . . .
C5 C 0.13037(9) 0.16494(17) 0.65706(6) 0.0293(4) Uani 1 1 d . . . . .
C6 C 0.12281(9) 0.29364(17) 0.67964(6) 0.0266(3) Uani 1 1 d . . . . .
C7 C 0.07894(10) 0.30035(19) 0.71662(7) 0.0336(4) Uani 1 1 d . . . . .
H7A H 0.046583 0.217548 0.712062 0.040 Uiso 1 1 calc R U . . .
H7B H 0.046711 0.383487 0.709281 0.040 Uiso 1 1 calc R U . . .
C8 C 0.12724(11) 0.3067(2) 0.77117(7) 0.0427(5) Uani 1 1 d . . . . .
H8A H 0.097422 0.276836 0.792923 0.051 Uiso 1 1 calc R U . . .
H8B H 0.168712 0.240266 0.776002 0.051 Uiso 1 1 calc R U . . .
C9 C 0.15857(12) 0.4506(2) 0.78734(7) 0.0449(5) Uani 1 1 d . . . . .
H9A H 0.188913 0.445632 0.822795 0.054 Uiso 1 1 calc R U . . .
H9B H 0.116787 0.514288 0.785437 0.054 Uiso 1 1 calc R U . . .
C10 C 0.20575(10) 0.5140(2) 0.75736(7) 0.0388(4) Uani 1 1 d . . . . .
H10A H 0.248014 0.451175 0.759679 0.047 Uiso 1 1 calc R U . . .
H10B H 0.226201 0.603177 0.773177 0.047 Uiso 1 1 calc R U . . .
C11 C 0.16578(9) 0.54122(17) 0.70190(6) 0.0283(3) Uani 1 1 d . . . . .
H11A H 0.115572 0.577335 0.698477 0.034 Uiso 1 1 calc R U . . .
H11B H 0.193001 0.613488 0.689429 0.034 Uiso 1 1 calc R U . . .
C12 C 0.15944(8) 0.41180(16) 0.67007(6) 0.0243(3) Uani 1 1 d . . . . .
C13 C 0.19757(8) 0.39768(16) 0.63478(6) 0.0237(3) Uani 1 1 d . . . . .
C14 C 0.14790(8) 0.55065(16) 0.52307(6) 0.0233(3) Uani 1 1 d . . . . .
C15 C 0.09181(9) 0.45230(17) 0.51730(6) 0.0273(3) Uani 1 1 d . . . . .
H15 H 0.074507 0.427886 0.544667 0.033 Uiso 1 1 calc R U . . .
C16 C 0.06190(9) 0.39107(18) 0.47110(6) 0.0295(4) Uani 1 1 d . . . . .
H16 H 0.024252 0.322973 0.467009 0.035 Uiso 1 1 calc R U . . .
C17 C 0.08586(9) 0.42721(18) 0.43039(6) 0.0285(4) Uani 1 1 d . . . . .
C18 C 0.14231(9) 0.52530(17) 0.43735(6) 0.0290(3) Uani 1 1 d . . . . .
H18 H 0.159486 0.550290 0.409988 0.035 Uiso 1 1 calc R U . . .
C19 C 0.17366(9) 0.58672(17) 0.48340(6) 0.0273(3) Uani 1 1 d . . . . .
H19 H 0.212351 0.652779 0.487791 0.033 Uiso 1 1 calc R U . . .
C20 C 0.05117(11) 0.3616(2) 0.38001(7) 0.0418(5) Uani 1 1 d . . . . .
H20A H 0.062229 0.261937 0.381880 0.063 Uiso 1 1 calc R U . . .
H20B H 0.071266 0.405058 0.355246 0.063 Uiso 1 1 calc R U . . .
H20C H -0.002524 0.375257 0.370147 0.063 Uiso 1 1 calc R U . . .
C21 C 0.33820(9) 0.49494(19) 0.57354(6) 0.0300(4) Uani 1 1 d . . . . .
C22 C 0.35069(11) 0.4551(2) 0.52897(7) 0.0406(4) Uani 1 1 d . . . . .
H22 H 0.320862 0.385266 0.508709 0.049 Uiso 1 1 calc R U . . .
C23 C 0.40684(12) 0.5178(3) 0.51424(9) 0.0525(6) Uani 1 1 d . . . . .
H23 H 0.414869 0.490922 0.483690 0.063 Uiso 1 1 calc R U . . .
C24 C 0.45095(12) 0.6183(2) 0.54331(9) 0.0513(6) Uani 1 1 d . . . . .
H24 H 0.489124 0.660618 0.532832 0.062 Uiso 1 1 calc R U . . .
C25 C 0.43957(10) 0.6574(2) 0.58771(9) 0.0435(5) Uani 1 1 d . . . . .
H25 H 0.470363 0.725963 0.608052 0.052 Uiso 1 1 calc R U . . .
C26 C 0.38337(9) 0.5970(2) 0.60275(7) 0.0348(4) Uani 1 1 d . . . . .
H26 H 0.375493 0.625245 0.633209 0.042 Uiso 1 1 calc R U . . .
C27 C 0.09995(12) -0.07648(19) 0.64908(8) 0.0446(5) Uani 1 1 d . . . . .
H27A H 0.078349 -0.070539 0.612743 0.067 Uiso 1 1 calc R U . . .
H27B H 0.073212 -0.146312 0.662375 0.067 Uiso 1 1 calc R U . . .
H27C H 0.152120 -0.103154 0.657117 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 0.38635(12) 0.3595(2) 0.71645(6) 0.0900(5) Uani 0.5 1 d D U P A -1
C28 C 0.4720(3) 0.4307(5) 0.7362(2) 0.0642(15) Uani 0.5 1 d D U P A -1
H28A H 0.472379 0.503423 0.761253 0.077 Uiso 0.5 1 calc R U P A -1
H28B H 0.482607 0.476443 0.707489 0.077 Uiso 0.5 1 calc R U P A -1
Cl2 Cl 0.54279(15) 0.3101(3) 0.76275(9) 0.1397(11) Uani 0.5 1 d D U P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 '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 119.56(7) . . ?
O1 S1 N1 106.90(7) . . ?
O2 S1 N1 107.01(7) . . ?
O1 S1 C14 109.70(7) . . ?
O2 S1 C14 108.33(7) . . ?
N1 S1 C14 104.24(7) . . ?
C5 O3 C27 116.92(15) . . ?
C13 N1 C1 105.03(12) . . ?
C13 N1 S1 114.20(10) . . ?
C1 N1 S1 111.66(10) . . ?
C2 C1 N1 109.70(14) . . ?
C2 C1 C21 129.19(15) . . ?
N1 C1 C21 120.96(15) . . ?
C1 C2 C3 109.02(14) . . ?
C4 C3 C13 120.27(15) . . ?
C4 C3 C2 132.42(15) . . ?
C13 C3 C2 107.10(14) . . ?
C5 C4 C3 117.54(15) . . ?
O3 C5 C4 123.05(15) . . ?
O3 C5 C6 114.67(15) . . ?
C4 C5 C6 122.20(15) . . ?
C12 C6 C5 120.13(15) . . ?
C12 C6 C7 120.18(15) . . ?
C5 C6 C7 119.57(15) . . ?
C6 C7 C8 113.61(14) . . ?
C9 C8 C7 113.40(16) . . ?
C8 C9 C10 116.13(17) . . ?
C9 C10 C11 115.72(15) . . ?
C12 C11 C10 112.64(14) . . ?
C13 C12 C6 116.65(14) . . ?
C13 C12 C11 122.08(14) . . ?
C6 C12 C11 120.72(14) . . ?
C12 C13 C3 122.71(15) . . ?
C12 C13 N1 128.04(14) . . ?
C3 C13 N1 108.84(14) . . ?
C19 C14 C15 121.02(15) . . ?
C19 C14 S1 120.01(12) . . ?
C15 C14 S1 118.97(12) . . ?
C16 C15 C14 118.83(15) . . ?
C15 C16 C17 121.32(15) . . ?
C16 C17 C18 118.55(15) . . ?
C16 C17 C20 120.43(16) . . ?
C18 C17 C20 121.01(16) . . ?
C19 C18 C17 121.13(15) . . ?
C18 C19 C14 119.14(15) . . ?
C22 C21 C26 118.76(17) . . ?
C22 C21 C1 120.46(17) . . ?
C26 C21 C1 120.72(15) . . ?
C23 C22 C21 119.9(2) . . ?
C24 C23 C22 120.8(2) . . ?
C23 C24 C25 119.75(19) . . ?
C24 C25 C26 120.2(2) . . ?
C25 C26 C21 120.56(18) . . ?
Cl1 C28 Cl2 113.9(3) . . ?
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 1.4279(12) . ?
S1 O2 1.4294(12) . ?
S1 N1 1.7143(13) . ?
S1 C14 1.7577(16) . ?
O3 C5 1.372(2) . ?
O3 C27 1.429(2) . ?
N1 C13 1.443(2) . ?
N1 C1 1.452(2) . ?
C1 C2 1.349(2) . ?
C1 C21 1.469(2) . ?
C2 C3 1.445(2) . ?
C3 C4 1.395(2) . ?
C3 C13 1.397(2) . ?
C4 C5 1.384(3) . ?
C5 C6 1.418(2) . ?
C6 C12 1.399(2) . ?
C6 C7 1.512(2) . ?
C7 C8 1.532(3) . ?
C8 C9 1.522(3) . ?
C9 C10 1.526(3) . ?
C10 C11 1.536(2) . ?
C11 C12 1.516(2) . ?
C12 C13 1.396(2) . ?
C14 C19 1.387(2) . ?
C14 C15 1.396(2) . ?
C15 C16 1.382(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.396(2) . ?
C17 C20 1.508(2) . ?
C18 C19 1.383(2) . ?
C21 C22 1.394(2) . ?
C21 C26 1.396(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.375(4) . ?
C24 C25 1.379(3) . ?
C25 C26 1.385(3) . ?
Cl1 C28 1.694(6) . ?
C28 Cl2 1.763(5) . ?
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 C13 167.03(11) . . . . ?
O2 S1 N1 C13 37.82(12) . . . . ?
C14 S1 N1 C13 -76.82(12) . . . . ?
O1 S1 N1 C1 -74.00(12) . . . . ?
O2 S1 N1 C1 156.80(11) . . . . ?
C14 S1 N1 C1 42.15(12) . . . . ?
C13 N1 C1 C2 4.76(17) . . . . ?
S1 N1 C1 C2 -119.53(13) . . . . ?
C13 N1 C1 C21 -171.04(14) . . . . ?
S1 N1 C1 C21 64.67(16) . . . . ?
N1 C1 C2 C3 -2.07(18) . . . . ?
C21 C1 C2 C3 173.28(16) . . . . ?
C1 C2 C3 C4 -176.12(17) . . . . ?
C1 C2 C3 C13 -1.56(18) . . . . ?
C13 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 173.20(16) . . . . ?
C27 O3 C5 C4 -3.3(2) . . . . ?
C27 O3 C5 C6 179.73(15) . . . . ?
C3 C4 C5 O3 -179.34(15) . . . . ?
C3 C4 C5 C6 -2.6(2) . . . . ?
O3 C5 C6 C12 177.38(14) . . . . ?
C4 C5 C6 C12 0.4(2) . . . . ?
O3 C5 C6 C7 1.3(2) . . . . ?
C4 C5 C6 C7 -175.70(15) . . . . ?
C12 C6 C7 C8 -73.5(2) . . . . ?
C5 C6 C7 C8 102.57(19) . . . . ?
C6 C7 C8 C9 79.0(2) . . . . ?
C7 C8 C9 C10 -58.0(2) . . . . ?
C8 C9 C10 C11 62.9(2) . . . . ?
C9 C10 C11 C12 -81.2(2) . . . . ?
C5 C6 C12 C13 5.0(2) . . . . ?
C7 C6 C12 C13 -178.86(14) . . . . ?
C5 C6 C12 C11 -166.68(14) . . . . ?
C7 C6 C12 C11 9.4(2) . . . . ?
C10 C11 C12 C13 -112.13(17) . . . . ?
C10 C11 C12 C6 59.1(2) . . . . ?
C6 C12 C13 C3 -8.6(2) . . . . ?
C11 C12 C13 C3 162.98(15) . . . . ?
C6 C12 C13 N1 179.45(14) . . . . ?
C11 C12 C13 N1 -8.9(2) . . . . ?
C4 C3 C13 C12 6.6(2) . . . . ?
C2 C3 C13 C12 -168.71(14) . . . . ?
C4 C3 C13 N1 179.93(14) . . . . ?
C2 C3 C13 N1 4.58(17) . . . . ?
C1 N1 C13 C12 167.13(15) . . . . ?
S1 N1 C13 C12 -70.21(18) . . . . ?
C1 N1 C13 C3 -5.69(16) . . . . ?
S1 N1 C13 C3 116.97(12) . . . . ?
O1 S1 C14 C19 7.39(15) . . . . ?
O2 S1 C14 C19 139.52(13) . . . . ?
N1 S1 C14 C19 -106.78(13) . . . . ?
O1 S1 C14 C15 -172.37(12) . . . . ?
O2 S1 C14 C15 -40.25(14) . . . . ?
N1 S1 C14 C15 73.45(13) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
S1 C14 C15 C16 179.60(12) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C15 C16 C17 C20 -178.51(16) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C20 C17 C18 C19 179.29(16) . . . . ?
C17 C18 C19 C14 -0.5(2) . . . . ?
C15 C14 C19 C18 0.9(2) . . . . ?
S1 C14 C19 C18 -178.84(12) . . . . ?
C2 C1 C21 C22 38.7(3) . . . . ?
N1 C1 C21 C22 -146.36(16) . . . . ?
C2 C1 C21 C26 -138.35(19) . . . . ?
N1 C1 C21 C26 36.5(2) . . . . ?
C26 C21 C22 C23 -0.6(3) . . . . ?
C1 C21 C22 C23 -177.74(17) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C21 0.7(3) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C1 C21 C26 C25 177.09(16) . . . . ?
