#------------------------------------------------------------------------------
#$Date: 2021-10-03 22:51:47 +0300 (Sun, 03 Oct 2021) $
#$Revision: 269484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519062.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_4519062
loop_
_publ_author_name
'Khake, Shrikant M.'
'Chatani, Naoto'
_publ_section_title
;
 Rh(III)-Catalyzed [3 + 2] Annulation of Aniline Derivatives with
 Vinylsilanes via C--H Activation/Alkene Cyclization: Access to Highly
 Regioselective Indoline Derivatives
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              12375
_journal_page_last               12383
_journal_paper_doi               10.1021/acscatal.1c03603
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C31 H27 N3 Si'
_chemical_formula_weight         469.64
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                109.919(6)
_cell_angle_beta                 90.438(4)
_cell_angle_gamma                106.701(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4517(5)
_cell_length_b                   10.5860(7)
_cell_length_c                   13.7057(7)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.99
_cell_measurement_theta_min      4.60
_cell_volume                     1226.40(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10259
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.044
_diffrn_reflns_theta_min         3.454
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0971
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2811
_refine_ls_wR_factor_ref         0.3174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3121
_reflns_number_total             4366
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03603_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1226.39(13)
_cod_database_code               4519062
_shelx_shelxl_version_number     2017/1
_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   0.494
_shelx_estimated_absorpt_t_max   0.821
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
C1 C 0.3973(4) 0.6071(4) 0.9201(3) 0.0330(9) Uani 1 1 d . . . . .
C2 C 0.3597(4) 0.4920(4) 0.8259(3) 0.0338(9) Uani 1 1 d . . . . .
C3 C 0.4693(5) 0.4500(5) 0.7691(3) 0.0434(11) Uani 1 1 d . . . . .
H3 H 0.443768 0.374502 0.703454 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6168(5) 0.5201(5) 0.8098(3) 0.0439(11) Uani 1 1 d . . . . .
H4 H 0.693753 0.495824 0.770664 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6522(5) 0.6259(4) 0.9078(3) 0.0409(10) Uani 1 1 d . . . . .
H5 H 0.753917 0.670020 0.935589 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5439(4) 0.6704(4) 0.9677(3) 0.0381(9) Uani 1 1 d . . . . .
C7 C 0.5890(5) 0.7726(5) 1.0783(3) 0.0420(10) Uani 1 1 d . . . . .
H7A H 0.604670 0.868914 1.079780 0.063 Uiso 1 1 calc R U . . .
H7B H 0.681346 0.765820 1.105889 0.063 Uiso 1 1 calc R U . . .
H7C H 0.510243 0.749807 1.121337 0.063 Uiso 1 1 calc R U . . .
C8 C 0.2413(4) 0.7601(4) 1.0027(3) 0.0344(9) Uani 1 1 d . . . . .
C9 C 0.3320(5) 1.0001(4) 1.0658(3) 0.0422(10) Uani 1 1 d . . . . .
H9 H 0.412665 1.084727 1.081733 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1929(5) 1.0105(4) 1.0905(3) 0.0442(11) Uani 1 1 d . . . . .
H10 H 0.175858 1.098955 1.122311 0.053 Uiso 1 1 calc R U . . .
C11 C 0.0816(5) 0.8850(4) 1.0661(3) 0.0425(10) Uani 1 1 d . . . . .
H11 H -0.015325 0.888693 1.081255 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1358(4) 0.5041(4) 0.9050(3) 0.0383(10) Uani 1 1 d . . . . .
H12A H 0.049153 0.531235 0.888525 0.046 Uiso 1 1 calc R U . . .
H12B H 0.106546 0.444680 0.948206 0.046 Uiso 1 1 calc R U . . .
C13 C 0.1921(4) 0.4240(4) 0.8032(3) 0.0358(9) Uani 1 1 d . . . . .
H13 H 0.168571 0.322898 0.796533 0.043 Uiso 1 1 calc R U . . .
C14 C 0.1384(4) 0.6196(4) 0.6971(3) 0.0367(9) Uani 1 1 d . . . . .
C15 C 0.2825(4) 0.7151(4) 0.7176(3) 0.0413(10) Uani 1 1 d . . . . .
H15 H 0.365237 0.682771 0.722544 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3069(5) 0.8557(5) 0.7307(3) 0.0436(10) Uani 1 1 d . . . . .
H16 H 0.405306 0.919161 0.745961 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1871(5) 0.9032(5) 0.7215(3) 0.0486(11) Uani 1 1 d . . . . .
H17 H 0.203567 0.998907 0.728405 0.058 Uiso 1 1 calc R U . . .
C18 C 0.0439(5) 0.8119(5) 0.7023(3) 0.0494(11) Uani 1 1 d . . . . .
H18 H -0.038194 0.845302 0.697624 0.059 Uiso 1 1 calc R U . . .
C19 C 0.0198(5) 0.6722(5) 0.6899(3) 0.0442(11) Uani 1 1 d . . . . .
H19 H -0.079207 0.610201 0.676157 0.053 Uiso 1 1 calc R U . . .
C20 C -0.0973(4) 0.3269(4) 0.6615(3) 0.0351(9) Uani 1 1 d . . . . .
C21 C -0.1626(4) 0.2676(4) 0.7331(3) 0.0373(9) Uani 1 1 d . . . . .
H21 H -0.104121 0.282354 0.794926 0.045 Uiso 1 1 calc R U . . .
C22 C -0.3125(5) 0.1869(4) 0.7156(3) 0.0419(10) Uani 1 1 d . . . . .
H22 H -0.355009 0.147176 0.765154 0.050 Uiso 1 1 calc R U . . .
C23 C -0.3983(4) 0.1653(4) 0.6262(3) 0.0434(11) Uani 1 1 d . . . . .
H23 H -0.500065 0.110210 0.613795 0.052 Uiso 1 1 calc R U . . .
C24 C -0.3356(5) 0.2242(5) 0.5541(3) 0.0432(10) Uani 1 1 d . . . . .
H24 H -0.395195 0.210334 0.492984 0.052 Uiso 1 1 calc R U . . .
C25 C -0.1866(5) 0.3031(4) 0.5709(3) 0.0421(10) Uani 1 1 d . . . . .
H25 H -0.144546 0.341371 0.520516 0.050 Uiso 1 1 calc R U . . .
C26 C 0.1932(4) 0.3360(4) 0.5668(3) 0.0363(9) Uani 1 1 d . . . . .
C27 C 0.2808(4) 0.4019(5) 0.5063(3) 0.0407(10) Uani 1 1 d . . . . .
H27 H 0.298513 0.500099 0.521739 0.049 Uiso 1 1 calc R U . . .
C28 C 0.3429(5) 0.3262(5) 0.4233(3) 0.0464(11) Uani 1 1 d . . . . .
H28 H 0.403598 0.372957 0.383244 0.056 Uiso 1 1 calc R U . . .
C29 C 0.3161(5) 0.1827(5) 0.3993(3) 0.0492(12) Uani 1 1 d . . . . .
H29 H 0.357371 0.130686 0.342145 0.059 Uiso 1 1 calc R U . . .
C30 C 0.2288(5) 0.1146(5) 0.4589(3) 0.0464(11) Uani 1 1 d . . . . .
H30 H 0.211912 0.016520 0.443620 0.056 Uiso 1 1 calc R U . . .
C31 C 0.1670(5) 0.1907(5) 0.5405(3) 0.0434(10) Uani 1 1 d . . . . .
H31 H 0.105165 0.143278 0.579640 0.052 Uiso 1 1 calc R U . . .
N1 N 0.2627(3) 0.6305(3) 0.9599(2) 0.0358(8) Uani 1 1 d . . . . .
N2 N 0.3581(4) 0.8765(3) 1.0206(2) 0.0375(8) Uani 1 1 d . . . . .
N3 N 0.0995(4) 0.7575(4) 1.0224(2) 0.0398(8) Uani 1 1 d . . . . .
Si1 Si 0.10593(11) 0.43014(11) 0.68119(7) 0.0348(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
C6 C1 C2 121.4(3) . . ?
C6 C1 N1 129.3(3) . . ?
C2 C1 N1 108.8(3) . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 C13 128.6(3) . . ?
C1 C2 C13 110.7(3) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 122.7(4) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C5 115.8(3) . . ?
C1 C6 C7 124.4(3) . . ?
C5 C6 C7 119.6(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N3 125.9(4) . . ?
N2 C8 N1 118.6(3) . . ?
N3 C8 N1 115.5(4) . . ?
N2 C9 C10 123.1(4) . . ?
N2 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C11 C10 C9 115.6(4) . . ?
C11 C10 H10 122.2 . . ?
C9 C10 H10 122.2 . . ?
N3 C11 C10 124.8(4) . . ?
N3 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
N1 C12 C13 105.1(3) . . ?
N1 C12 H12A 110.7 . . ?
C13 C12 H12A 110.7 . . ?
N1 C12 H12B 110.7 . . ?
C13 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C2 C13 C12 102.8(3) . . ?
C2 C13 Si1 114.8(3) . . ?
C12 C13 Si1 113.8(3) . . ?
C2 C13 H13 108.4 . . ?
C12 C13 H13 108.4 . . ?
Si1 C13 H13 108.4 . . ?
C15 C14 C19 117.2(4) . . ?
C15 C14 Si1 121.2(3) . . ?
C19 C14 Si1 121.6(3) . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.7(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.5(4) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C21 C20 C25 118.0(4) . . ?
C21 C20 Si1 121.9(3) . . ?
C25 C20 Si1 120.1(3) . . ?
C20 C21 C22 121.3(4) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 120.7(4) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C27 C26 C31 117.9(3) . . ?
C27 C26 Si1 124.0(3) . . ?
C31 C26 Si1 118.1(3) . . ?
C26 C27 C28 121.0(4) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 119.9(4) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.0(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 119.4(4) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C26 121.7(4) . . ?
C30 C31 H31 119.2 . . ?
C26 C31 H31 119.2 . . ?
C8 N1 C1 125.0(3) . . ?
C8 N1 C12 120.2(3) . . ?
C1 N1 C12 108.9(3) . . ?
C9 N2 C8 116.1(3) . . ?
C11 N3 C8 114.5(4) . . ?
C14 Si1 C20 112.80(18) . . ?
C14 Si1 C13 108.55(17) . . ?
C20 Si1 C13 107.77(18) . . ?
C14 Si1 C26 112.06(18) . . ?
C20 Si1 C26 107.37(16) . . ?
C13 Si1 C26 108.11(17) . . ?
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
C1 C6 1.396(6) . ?
C1 C2 1.396(5) . ?
C1 N1 1.442(5) . ?
C2 C3 1.385(5) . ?
C2 C13 1.520(5) . ?
C3 C4 1.385(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N2 1.344(5) . ?
C8 N3 1.364(5) . ?
C8 N1 1.371(5) . ?
C9 N2 1.339(5) . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.368(6) . ?
C10 H10 0.9500 . ?
C11 N3 1.338(5) . ?
C11 H11 0.9500 . ?
C12 N1 1.474(5) . ?
C12 C13 1.553(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 Si1 1.883(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.402(6) . ?
C14 C19 1.403(6) . ?
C14 Si1 1.874(4) . ?
C15 C16 1.385(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.394(6) . ?
C20 C25 1.402(6) . ?
C20 Si1 1.882(4) . ?
C21 C22 1.397(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(6) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.391(6) . ?
C26 C31 1.399(6) . ?
C26 Si1 1.886(4) . ?
C27 C28 1.393(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.392(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
