#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:30:11 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159723.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_7159723
loop_
_publ_author_name
'Jain, Anshul'
'Kumari, Akanksha'
'Metre, Ramesh K.'
'Rana, Nirmal K.'
_publ_section_title
;
 Diastereoselective synthesis of trans-2,3-dihydroindoles
 via formal [4 + 1] annulation reactions of a sulfonium ylide.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              621
_journal_page_last               632
_journal_paper_doi               10.1039/d3ob01793a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C30 H25 N O4 S'
_chemical_formula_sum            'C30 H25 N O4 S'
_chemical_formula_weight         495.57
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2022-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-11 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.685(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1168(14)
_cell_length_b                   17.929(3)
_cell_length_c                   16.686(3)
_cell_measurement_reflns_used    9132
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.45
_cell_volume                     2420.1(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35876
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_min         2.762
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9338.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             1040.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0444
_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          0.1426
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5223
_reflns_number_total             5987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01793a2.cif
_cod_data_source_block           23apra_0m
_cod_depositor_comments          'Adding full bibliography for 7159723.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159723
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.14384(4) 0.22481(2) 0.11080(2) 0.01250(12) Uani 1 1 d . . . . .
O1 O 0.23998(12) 0.15814(6) 0.12481(7) 0.0177(2) Uani 1 1 d . . . . .
O2 O 0.21795(12) 0.29028(6) 0.07986(6) 0.0169(2) Uani 1 1 d . . . . .
O3 O -0.16788(15) 0.22816(6) -0.11878(7) 0.0219(3) Uani 1 1 d . . . . .
O4 O -0.37642(15) 0.38624(6) 0.02171(7) 0.0227(3) Uani 1 1 d . . . . .
N1 N -0.01126(14) 0.20301(7) 0.04392(7) 0.0124(3) Uani 1 1 d . . . . .
C1 C -0.10907(17) 0.13808(8) 0.05648(8) 0.0125(3) Uani 1 1 d . . . . .
C2 C -0.05416(18) 0.06587(8) 0.07140(10) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.058015 0.054531 0.075254 0.022 Uiso 1 1 calc R . . . .
C3 C -0.1717(2) 0.01096(9) 0.08042(10) 0.0203(3) Uani 1 1 d . . . . .
H3 H -0.137741 -0.037879 0.090794 0.024 Uiso 1 1 calc R . . . .
C4 C -0.33965(19) 0.02776(8) 0.07418(9) 0.0173(3) Uani 1 1 d . . . . .
H4 H -0.416458 -0.009848 0.080445 0.021 Uiso 1 1 calc R . . . .
C5 C -0.39352(17) 0.10037(8) 0.05866(9) 0.0146(3) Uani 1 1 d . . . . .
H5 H -0.505755 0.111601 0.054324 0.017 Uiso 1 1 calc R . . . .
C6 C -0.27685(17) 0.15590(8) 0.04971(8) 0.0123(3) Uani 1 1 d . . . . .
C7 C -0.30281(17) 0.23780(8) 0.03321(9) 0.0117(3) Uani 1 1 d . . . . .
H7 H -0.377431 0.244274 -0.015498 0.014 Uiso 1 1 calc R . . . .
C8 C -0.12676(17) 0.26535(8) 0.01729(9) 0.0116(3) Uani 1 1 d . . . . .
H8 H -0.098506 0.311270 0.047182 0.014 Uiso 1 1 calc R . . . .
C9 C -0.11022(18) 0.27596(8) -0.07323(9) 0.0140(3) Uani 1 1 d . . . . .
C10 C -0.02244(17) 0.34175(8) -0.10405(9) 0.0140(3) Uani 1 1 d . . . . .
C11 C 0.05403(19) 0.39695(9) -0.05493(10) 0.0191(3) Uani 1 1 d . . . . .
H11 H 0.049718 0.394338 0.000527 0.023 Uiso 1 1 calc R . . . .
C12 C 0.1366(2) 0.45579(9) -0.08848(11) 0.0253(4) Uani 1 1 d . . . . .
H12 H 0.188045 0.492120 -0.055451 0.030 Uiso 1 1 calc R . . . .
C13 C 0.1420(2) 0.46020(10) -0.17102(11) 0.0271(4) Uani 1 1 d . . . . .
H13 H 0.197957 0.499348 -0.193333 0.032 Uiso 1 1 calc R . . . .
C14 C 0.0642(2) 0.40631(10) -0.22078(10) 0.0251(4) Uani 1 1 d . . . . .
H14 H 0.066875 0.409816 -0.276266 0.030 Uiso 1 1 calc R . . . .
C15 C -0.01728(19) 0.34752(9) -0.18765(9) 0.0192(3) Uani 1 1 d . . . . .
H15 H -0.069017 0.311536 -0.221053 0.023 Uiso 1 1 calc R . . . .
C16 C -0.37429(17) 0.27762(7) 0.10378(9) 0.0127(3) Uani 1 1 d . . . . .
H16A H -0.473917 0.252088 0.116968 0.015 Uiso 1 1 calc R . . . .
H16B H -0.295046 0.275286 0.150487 0.015 Uiso 1 1 calc R . . . .
C17 C -0.41492(17) 0.35894(8) 0.08439(9) 0.0148(3) Uani 1 1 d . . . . .
C18 C -0.50288(17) 0.40340(8) 0.14310(9) 0.0147(3) Uani 1 1 d . . . . .
C19 C -0.56798(19) 0.47260(9) 0.11821(10) 0.0196(3) Uani 1 1 d . . . . .
H19 H -0.552841 0.490220 0.066910 0.024 Uiso 1 1 calc R . . . .
C20 C -0.6552(2) 0.51503(9) 0.17005(11) 0.0226(3) Uani 1 1 d . . . . .
H20 H -0.698799 0.560923 0.153222 0.027 Uiso 1 1 calc R . . . .
C21 C -0.6777(2) 0.48931(9) 0.24684(10) 0.0216(3) Uani 1 1 d . . . . .
H21 H -0.736226 0.517996 0.281278 0.026 Uiso 1 1 calc R . . . .
C22 C -0.61287(19) 0.42070(9) 0.27238(10) 0.0193(3) Uani 1 1 d . . . . .
H22 H -0.627521 0.403547 0.323921 0.023 Uiso 1 1 calc R . . . .
C23 C -0.52597(17) 0.37780(8) 0.22049(9) 0.0158(3) Uani 1 1 d . . . . .
H23 H -0.483022 0.331827 0.237444 0.019 Uiso 1 1 calc R . . . .
C24 C 0.05366(16) 0.24888(8) 0.19924(8) 0.0122(3) Uani 1 1 d . . . . .
C25 C 0.02809(17) 0.32379(8) 0.21661(9) 0.0147(3) Uani 1 1 d . . . . .
H25 H 0.066272 0.361114 0.184140 0.018 Uiso 1 1 calc R . . . .
C26 C -0.05571(18) 0.34163(8) 0.28353(9) 0.0158(3) Uani 1 1 d . . . . .
H26 H -0.074053 0.391462 0.295477 0.019 Uiso 1 1 calc R . . . .
C27 C -0.11274(18) 0.28624(8) 0.33304(9) 0.0145(3) Uani 1 1 d . . . . .
C28 C -0.08206(18) 0.21178(8) 0.31499(9) 0.0163(3) Uani 1 1 d . . . . .
H28 H -0.116954 0.174386 0.348331 0.020 Uiso 1 1 calc R . . . .
C29 C -0.00022(17) 0.19264(9) 0.24801(9) 0.0163(3) Uani 1 1 d . . . . .
H29 H 0.018246 0.142834 0.235994 0.020 Uiso 1 1 calc R . . . .
C30 C -0.20800(19) 0.30592(9) 0.40360(9) 0.0185(3) Uani 1 1 d . . . . .
H30A H -0.161296 0.349851 0.429319 0.028 Uiso 1 1 calc GR . . . .
H30B H -0.202177 0.265312 0.441219 0.028 Uiso 1 1 calc GR . . . .
H30C H -0.321385 0.315180 0.385339 0.028 Uiso 1 1 calc GR . . . .
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 N1 106.60(6) . . ?
O1 S1 C24 109.05(7) . . ?
O2 S1 O1 120.10(6) . . ?
O2 S1 N1 105.56(6) . . ?
O2 S1 C24 108.51(7) . . ?
N1 S1 C24 106.14(6) . . ?
C1 N1 S1 119.45(9) . . ?
C1 N1 C8 107.91(10) . . ?
C8 N1 S1 116.38(9) . . ?
C2 C1 N1 127.67(13) . . ?
C2 C1 C6 121.77(13) . . ?
C6 C1 N1 110.54(12) . . ?
C1 C2 C3 117.94(14) . . ?
C2 C3 C4 121.09(14) . . ?
C5 C4 C3 120.51(14) . . ?
C6 C5 C4 118.92(13) . . ?
C1 C6 C7 111.07(12) . . ?
C5 C6 C1 119.77(13) . . ?
C5 C6 C7 129.17(13) . . ?
C6 C7 C8 102.96(11) . . ?
C6 C7 C16 111.73(12) . . ?
C16 C7 C8 113.23(11) . . ?
N1 C8 C7 105.84(11) . . ?
N1 C8 C9 106.25(11) . . ?
C9 C8 C7 111.21(12) . . ?
O3 C9 C8 117.86(13) . . ?
O3 C9 C10 120.88(14) . . ?
C10 C9 C8 121.25(12) . . ?
C11 C10 C9 124.03(14) . . ?
C11 C10 C15 118.89(14) . . ?
C15 C10 C9 117.08(13) . . ?
C12 C11 C10 120.41(15) . . ?
C13 C12 C11 119.95(16) . . ?
C12 C13 C14 120.28(15) . . ?
C15 C14 C13 119.95(16) . . ?
C14 C15 C10 120.51(15) . . ?
C17 C16 C7 111.83(12) . . ?
O4 C17 C16 120.03(13) . . ?
O4 C17 C18 121.32(13) . . ?
C18 C17 C16 118.65(13) . . ?
C19 C18 C17 117.99(14) . . ?
C23 C18 C17 122.66(13) . . ?
C23 C18 C19 119.33(14) . . ?
C20 C19 C18 120.04(15) . . ?
C21 C20 C19 120.36(15) . . ?
C20 C21 C22 120.11(15) . . ?
C21 C22 C23 119.74(15) . . ?
C22 C23 C18 120.42(14) . . ?
C25 C24 S1 119.47(11) . . ?
C29 C24 S1 119.17(12) . . ?
C29 C24 C25 121.24(13) . . ?
C26 C25 C24 118.66(13) . . ?
C25 C26 C27 121.28(14) . . ?
C26 C27 C28 118.66(13) . . ?
C26 C27 C30 120.92(14) . . ?
C28 C27 C30 120.41(14) . . ?
C29 C28 C27 121.03(14) . . ?
C24 C29 C28 119.10(14) . . ?
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 1.4361(11) . ?
S1 O2 1.4342(11) . ?
S1 N1 1.6593(12) . ?
S1 C24 1.7539(14) . ?
O3 C9 1.2136(18) . ?
O4 C17 1.2185(19) . ?
N1 C1 1.4340(18) . ?
N1 C8 1.5026(17) . ?
C1 C2 1.385(2) . ?
C1 C6 1.3944(19) . ?
C2 C3 1.388(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.5055(19) . ?
C7 C8 1.5551(19) . ?
C7 C16 1.5313(19) . ?
C8 C9 1.539(2) . ?
C9 C10 1.491(2) . ?
C10 C11 1.398(2) . ?
C10 C15 1.403(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.384(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.383(2) . ?
C16 C17 1.5237(19) . ?
C17 C18 1.490(2) . ?
C18 C19 1.398(2) . ?
C18 C23 1.397(2) . ?
C19 C20 1.389(2) . ?
C20 C21 1.388(2) . ?
C21 C22 1.391(2) . ?
C22 C23 1.392(2) . ?
C24 C25 1.393(2) . ?
C24 C29 1.389(2) . ?
C25 C26 1.391(2) . ?
C26 C27 1.395(2) . ?
C27 C28 1.395(2) . ?
C27 C30 1.5023(19) . ?
C28 C29 1.389(2) . ?
