#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:07:04 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289337 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/24/7132406.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_7132406
loop_
_publ_author_name
'Gharpure, Santosh J.'
'Kumari, Sanyog'
_publ_section_title
;
 Cascade radical cyclization on 3-propargyl-2-alkenyl indole gives
 stereoselective access to cyclohepta[b]indole over carbazole.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              538
_journal_page_last               541
_journal_paper_doi               10.1039/d3cc05237k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C32 H25 N S'
_chemical_formula_sum            'C32 H25 N S'
_chemical_formula_weight         455.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-09-22 deposited with the CCDC.	2023-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                95.743(6)
_cell_angle_beta                 112.337(6)
_cell_angle_gamma                116.102(6)
_cell_formula_units_Z            2
_cell_length_a                   10.4151(5)
_cell_length_b                   11.5788(8)
_cell_length_c                   12.6011(9)
_cell_measurement_reflns_used    4565
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      25.1610
_cell_measurement_theta_min      1.8470
_cell_volume                     1195.11(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -20.08 339.92   1.00    2.00 -25.84   0.00  59.25    --   360
  2  ω     -1.00  46.00   1.00    2.00    --    0.00 -94.56-145.16   47
  3  ω    -71.47  -9.47   1.00    2.00    --  -17.90 107.43  -1.09   62
  4  ω    -90.97  25.03   1.00    2.00    --    0.00 -59.25 164.08  116
  5  ω    -90.97  25.03   1.00    2.00    --    0.00 -59.25  92.08  116
  6  ω    -90.97  25.03   1.00    2.00    --    0.00 -59.25 -51.92  116
  7  ω    -90.97  25.03   1.00    2.00    --    0.00 -59.25  20.08  116
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0082686000
_diffrn_orient_matrix_UB_12      -0.0438966000
_diffrn_orient_matrix_UB_13      0.0355725000
_diffrn_orient_matrix_UB_21      -0.0857622000
_diffrn_orient_matrix_UB_22      -0.0331789000
_diffrn_orient_matrix_UB_23      -0.0339146000
_diffrn_orient_matrix_UB_31      -0.0003364000
_diffrn_orient_matrix_UB_32      -0.0465086000
_diffrn_orient_matrix_UB_33      -0.0414182000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34821
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.845
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0484
_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)+(0.0709P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2994
_reflns_number_total             4207
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05237k2.cif
_cod_data_source_block           sjg_negi_03_267_autored
_cod_depositor_comments
'Adding full bibliography for 7132403--7132408.cif.'
_cod_original_cell_volume        1195.11(15)
_cod_database_code               7132406
_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.
;
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 65.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.02
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X)
2.b Idealised Me refined as rotating group:
 C00P(H00B,H00C,H00F), C00Y(H00K,H00P,H00Y)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.644
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S01 S 0.71669(7) 0.48619(6) 0.79574(6) 0.0328(2) Uani 1 1 d . . . . .
N002 N 0.0864(2) 0.45158(18) 0.64504(17) 0.0299(5) Uani 1 1 d . . . . .
C003 C 0.3938(3) 0.3870(2) 0.6452(2) 0.0271(5) Uani 1 1 d . . . . .
C004 C 0.5271(3) 0.5809(2) 0.8271(2) 0.0280(5) Uani 1 1 d . . . . .
C005 C 0.3896(3) 0.2796(2) 0.5648(2) 0.0289(5) Uani 1 1 d . . . . .
C006 C 0.6977(3) 0.3613(2) 0.8696(2) 0.0294(6) Uani 1 1 d . . . . .
C007 C 0.5324(3) 0.4833(2) 0.7530(2) 0.0285(5) Uani 1 1 d . . . . .
C008 C 0.2485(3) 0.3855(2) 0.6129(2) 0.0274(5) Uani 1 1 d . . . . .
C009 C 0.2428(3) 0.4781(2) 0.6902(2) 0.0273(5) Uani 1 1 d . . . . .
C00A C 0.3816(3) 0.5775(2) 0.7954(2) 0.0293(5) Uani 1 1 d . . . . .
H00A H 0.376977 0.641898 0.844504 0.035 Uiso 1 1 calc R . . . .
C00B C 0.0861(3) 0.3026(2) 0.5116(2) 0.0291(5) Uani 1 1 d . . . . .
C00C C -0.0102(3) 0.3466(2) 0.5353(2) 0.0295(5) Uani 1 1 d . . . . .
C00D C 0.4509(3) 0.3061(2) 0.4840(2) 0.0326(6) Uani 1 1 d . . . . .
H00D H 0.506769 0.396795 0.484087 0.039 Uiso 1 1 calc R . . . .
C00E C 0.5626(3) 0.2829(2) 0.8833(2) 0.0334(6) Uani 1 1 d . . . . .
H00E H 0.471632 0.293931 0.851613 0.040 Uiso 1 1 calc R . . . .
C00F C 0.3525(3) 0.0676(2) 0.4022(2) 0.0330(6) Uani 1 1 d . . . . .
C00G C 0.8298(3) 0.3430(2) 0.9168(2) 0.0338(6) Uani 1 1 d . . . . .
H00G H 0.922513 0.395222 0.907150 0.041 Uiso 1 1 calc R . . . .
C00H C 0.0127(3) 0.1984(2) 0.4034(2) 0.0331(6) Uani 1 1 d . . . . .
H00H H 0.073902 0.166207 0.385043 0.040 Uiso 1 1 calc R . . . .
C00I C 0.4316(3) 0.2020(2) 0.4033(2) 0.0355(6) Uani 1 1 d . . . . .
H00I H 0.472786 0.222022 0.347651 0.043 Uiso 1 1 calc R . . . .
C00J C 0.3092(3) 0.1464(2) 0.5632(2) 0.0339(6) Uani 1 1 d . . . . .
H00J H 0.265411 0.125994 0.617345 0.041 Uiso 1 1 calc R . . . .
C00K C 0.6720(3) 0.6880(2) 0.9416(2) 0.0301(6) Uani 1 1 d . . . . .
C00L C 0.2923(3) 0.0429(2) 0.4832(2) 0.0371(6) Uani 1 1 d . . . . .
H00L H 0.237717 -0.047496 0.484172 0.044 Uiso 1 1 calc R . . . .
C00M C -0.1734(3) 0.2905(2) 0.4560(2) 0.0335(6) Uani 1 1 d . . . . .
H00M H -0.236232 0.320875 0.474019 0.040 Uiso 1 1 calc R . . . .
C00N C 0.5601(3) 0.1886(2) 0.9431(2) 0.0383(6) Uani 1 1 d . . . . .
H00N H 0.466841 0.134832 0.951571 0.046 Uiso 1 1 calc R . . . .
C00O C 0.7378(3) 0.6560(2) 1.0440(2) 0.0372(6) Uani 1 1 d . . . . .
H00O H 0.695546 0.563399 1.039907 0.045 Uiso 1 1 calc R . . . .
C00P C 0.0263(3) 0.5129(2) 0.7060(2) 0.0369(6) Uani 1 1 d . . . . .
H00B H 0.107657 0.561590 0.791448 0.055 Uiso 1 1 calc GR . . . .
H00C H -0.074828 0.441583 0.700113 0.055 Uiso 1 1 calc GR . . . .
H00F H 0.005809 0.576632 0.667218 0.055 Uiso 1 1 calc GR . . . .
C00Q C 0.6916(3) 0.1717(2) 0.9907(2) 0.0419(7) Uani 1 1 d . . . . .
H00Q H 0.689213 0.107223 1.032217 0.050 Uiso 1 1 calc R . . . .
C00R C -0.2420(3) 0.1882(2) 0.3495(2) 0.0392(6) Uani 1 1 d . . . . .
H00R H -0.353588 0.148330 0.293187 0.047 Uiso 1 1 calc R . . . .
C00S C -0.1498(3) 0.1431(2) 0.3238(2) 0.0372(6) Uani 1 1 d . . . . .
H00S H -0.199700 0.072956 0.250056 0.045 Uiso 1 1 calc R . . . .
C00T C 0.8267(3) 0.2495(2) 0.9774(2) 0.0400(6) Uani 1 1 d . . . . .
H00T H 0.917660 0.238634 1.010131 0.048 Uiso 1 1 calc R . . . .
C00U C 0.9271(3) 0.8915(3) 1.1594(2) 0.0401(6) Uani 1 1 d . . . . .
H00U H 1.013479 0.960676 1.233710 0.048 Uiso 1 1 calc R . . . .
C00V C 0.8637(3) 0.7565(3) 1.1518(2) 0.0410(6) Uani 1 1 d . . . . .
H00V H 0.906964 0.732547 1.221164 0.049 Uiso 1 1 calc R . . . .
C00W C 0.8643(3) 0.9250(2) 1.0586(2) 0.0433(7) Uani 1 1 d . . . . .
H00W H 0.907992 1.017784 1.063214 0.052 Uiso 1 1 calc R . . . .
C00X C 0.7371(3) 0.8243(2) 0.9497(2) 0.0386(6) Uani 1 1 d . . . . .
H00X H 0.694469 0.848752 0.880604 0.046 Uiso 1 1 calc R . . . .
C00Y C 0.3333(3) -0.0458(3) 0.3160(2) 0.0471(7) Uani 1 1 d . . . . .
H00K H 0.304002 -0.033807 0.236013 0.071 Uiso 1 1 calc GR . . . .
H00P H 0.247461 -0.132993 0.309675 0.071 Uiso 1 1 calc GR . . . .
H00Y H 0.435827 -0.044354 0.346236 0.071 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'
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
C007 S01 C006 103.48(11) . . ?
C009 N002 C00C 108.53(18) . . ?
C009 N002 C00P 126.5(2) . . ?
C00C N002 C00P 124.8(2) . . ?
C007 C003 C005 123.4(2) . . ?
C007 C003 C008 118.9(2) . . ?
C008 C003 C005 117.6(2) . . ?
C007 C004 C00K 123.0(2) . . ?
C00A C004 C007 120.1(2) . . ?
C00A C004 C00K 116.92(19) . . ?
C00D C005 C003 122.3(2) . . ?
C00J C005 C003 119.0(2) . . ?
C00J C005 C00D 118.5(2) . . ?
C00E C006 S01 124.59(18) . . ?
C00E C006 C00G 118.9(2) . . ?
C00G C006 S01 116.51(18) . . ?
C003 C007 S01 119.61(17) . . ?
C003 C007 C004 120.6(2) . . ?
C004 C007 S01 119.75(17) . . ?
C003 C008 C009 119.9(2) . . ?
C003 C008 C00B 133.9(2) . . ?
C009 C008 C00B 106.27(19) . . ?
N002 C009 C008 109.71(19) . . ?
N002 C009 C00A 128.8(2) . . ?
C00A C009 C008 121.5(2) . . ?
C004 C00A C009 118.8(2) . . ?
C00C C00B C008 106.45(19) . . ?
C00H C00B C008 135.2(2) . . ?
C00H C00B C00C 118.4(2) . . ?
N002 C00C C00B 108.9(2) . . ?
C00M C00C N002 128.6(2) . . ?
C00M C00C C00B 122.5(2) . . ?
C00I C00D C005 120.7(2) . . ?
C00N C00E C006 120.1(2) . . ?
C00I C00F C00Y 121.4(2) . . ?
C00L C00F C00I 117.4(2) . . ?
C00L C00F C00Y 121.2(2) . . ?
C00T C00G C006 120.5(2) . . ?
C00S C00H C00B 119.2(2) . . ?
C00D C00I C00F 121.1(2) . . ?
C00L C00J C005 120.5(2) . . ?
C00O C00K C004 121.6(2) . . ?
C00O C00K C00X 118.3(2) . . ?
C00X C00K C004 120.0(2) . . ?
C00F C00L C00J 121.8(2) . . ?
C00C C00M C00R 117.7(2) . . ?
C00Q C00N C00E 120.9(2) . . ?
C00V C00O C00K 121.1(2) . . ?
C00N C00Q C00T 119.4(2) . . ?
C00M C00R C00S 121.0(2) . . ?
C00H C00S C00R 121.2(2) . . ?
C00G C00T C00Q 120.3(2) . . ?
C00W C00U C00V 119.3(2) . . ?
C00U C00V C00O 120.3(2) . . ?
C00U C00W C00X 120.6(2) . . ?
C00K C00X C00W 120.3(2) . . ?
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
S01 C006 1.776(2) . ?
S01 C007 1.769(2) . ?
N002 C009 1.375(3) . ?
N002 C00C 1.390(3) . ?
N002 C00P 1.460(3) . ?
C003 C005 1.497(3) . ?
C003 C007 1.401(3) . ?
C003 C008 1.402(3) . ?
C004 C007 1.426(3) . ?
C004 C00A 1.394(3) . ?
C004 C00K 1.496(3) . ?
C005 C00D 1.387(3) . ?
C005 C00J 1.387(3) . ?
C006 C00E 1.388(3) . ?
C006 C00G 1.398(3) . ?
C008 C009 1.411(3) . ?
C008 C00B 1.448(3) . ?
C009 C00A 1.395(3) . ?
C00B C00C 1.416(3) . ?
C00B C00H 1.402(3) . ?
C00C C00M 1.384(3) . ?
C00D C00I 1.384(3) . ?
C00E C00N 1.384(3) . ?
C00F C00I 1.400(3) . ?
C00F C00L 1.380(3) . ?
C00F C00Y 1.503(3) . ?
C00G C00T 1.382(3) . ?
C00H C00S 1.381(3) . ?
C00J C00L 1.386(3) . ?
C00K C00O 1.385(3) . ?
C00K C00X 1.390(3) . ?
C00M C00R 1.386(3) . ?
C00N C00Q 1.381(4) . ?
C00O C00V 1.381(3) . ?
C00Q C00T 1.383(4) . ?
C00R C00S 1.395(3) . ?
C00U C00V 1.380(4) . ?
C00U C00W 1.371(4) . ?
C00W C00X 1.392(3) . ?
