#------------------------------------------------------------------------------
#$Date: 2021-05-03 22:22:41 +0300 (Mon, 03 May 2021) $
#$Revision: 264789 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/86/4518671.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_4518671
loop_
_publ_author_name
'Khake, Shrikant M.'
'Yamazaki, Ken'
'Ano, Yusuke'
'Chatani, Naoto'
_publ_section_title
;
 Iridium(III)-Catalyzed Branch-Selective C--H Alkenylation of Aniline
 Derivatives with Alkenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5463
_journal_page_last               5471
_journal_paper_doi               10.1021/acscatal.1c00714
_journal_year                    2021
_chemical_formula_moiety         'C16 H21 N3 Si'
_chemical_formula_sum            'C16 H21 N3 Si'
_chemical_formula_weight         283.45
_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
_cell_angle_alpha                95.532(3)
_cell_angle_beta                 92.916(3)
_cell_angle_gamma                111.087(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5057(4)
_cell_length_b                   10.2435(6)
_cell_length_c                   10.4050(2)
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    123
_cell_measurement_theta_max      67.86
_cell_measurement_theta_min      4.34
_cell_volume                     838.34(7)
_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    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7410
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.030
_diffrn_reflns_theta_max         68.030
_diffrn_reflns_theta_min         4.287
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.179
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.535
_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            colorless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             304.00
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.24
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1154P)²+0.5268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                2653
_reflns_number_total             3028
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cs1c00714_si_002.cif
_cod_data_source_block           xcalibur
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 7550 2019-12-06 10:49:48Z antanas 
;
_cod_database_code               4518671
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.48934(10) 0.13459(7) 0.26464(7) 0.0405(3) Uani 1 1 d . . .
N1 N 0.3808(3) 0.4263(2) 0.3318(2) 0.0317(5) Uani 1 1 d . . .
N2 N 0.5299(3) 0.5329(2) 0.16545(18) 0.0314(5) Uani 1 1 d . . .
N3 N 0.6399(3) 0.6022(2) 0.38915(19) 0.0344(5) Uani 1 1 d . . .
C1 C 0.2322(3) 0.3453(3) 0.2483(2) 0.0307(5) Uani 1 1 d . . .
C2 C 0.1380(3) 0.4122(3) 0.1879(3) 0.0402(6) Uani 1 1 d . . .
C3 C -0.0063(4) 0.3289(3) 0.1062(3) 0.0480(7) Uani 1 1 d . . .
C4 C -0.0546(4) 0.1847(3) 0.0861(3) 0.0497(8) Uani 1 1 d . . .
C5 C 0.0329(4) 0.1193(3) 0.1534(3) 0.0485(7) Uani 1 1 d . . .
C6 C 0.1783(3) 0.1979(3) 0.2368(3) 0.0379(6) Uani 1 1 d . . .
C7 C 0.1883(5) 0.5704(3) 0.2073(4) 0.0518(8) Uani 1 1 d . . .
C8 C 0.5201(3) 0.5238(2) 0.2937(2) 0.0291(5) Uani 1 1 d . . .
C9 C 0.7823(3) 0.6918(3) 0.3509(2) 0.0374(6) Uani 1 1 d . . .
C10 C 0.8068(3) 0.7063(3) 0.2220(2) 0.0357(6) Uani 1 1 d . . .
C11 C 0.6744(3) 0.6240(3) 0.1326(2) 0.0331(6) Uani 1 1 d . . .
C12 C 0.2708(4) 0.1229(3) 0.3065(3) 0.0401(6) Uani 1 1 d . . .
C13 C 0.1896(5) 0.0314(4) 0.3861(3) 0.0570(9) Uani 1 1 d . . .
C14 C 0.5020(6) -0.0442(4) 0.2667(4) 0.0566(9) Uani 1 1 d . . .
C15 C 0.6625(5) 0.2583(4) 0.3838(4) 0.0547(8) Uani 1 1 d . . .
C16 C 0.5063(4) 0.1840(3) 0.0959(3) 0.0430(7) Uani 1 1 d . . .
H1 H -0.077(4) 0.372(4) 0.061(3) 0.046(8) Uiso 1 1 d . . .
H2 H -0.149(5) 0.131(4) 0.033(4) 0.067(11) Uiso 1 1 d . . .
H3 H -0.004(6) 0.008(5) 0.144(4) 0.084(13) Uiso 1 1 d . . .
H4 H 0.216(5) 0.593(4) 0.309(4) 0.063(10) Uiso 1 1 d . . .
H5 H 0.275(5) 0.614(4) 0.144(4) 0.056(10) Uiso 1 1 d . . .
H6 H 0.088(6) 0.599(5) 0.191(5) 0.093(15) Uiso 1 1 d . . .
H7 H 0.382(4) 0.422(3) 0.404(3) 0.031(7) Uiso 1 1 d . . .
H8 H 0.865(4) 0.745(3) 0.420(3) 0.047(8) Uiso 1 1 d . . .
H9 H 0.909(4) 0.772(4) 0.200(3) 0.049(9) Uiso 1 1 d . . .
H10 H 0.680(4) 0.625(3) 0.044(3) 0.031(7) Uiso 1 1 d . . .
H11 H 0.086(5) 0.025(4) 0.402(3) 0.052(10) Uiso 1 1 d . . .
H12 H 0.239(6) -0.023(5) 0.433(4) 0.079(13) Uiso 1 1 d . . .
H13 H 0.409(5) -0.117(4) 0.211(4) 0.059(10) Uiso 1 1 d . . .
H14 H 0.497(5) -0.062(4) 0.334(4) 0.066(13) Uiso 1 1 d . . .
H15 H 0.622(6) -0.037(5) 0.247(4) 0.083(13) Uiso 1 1 d . . .
H16 H 0.643(5) 0.249(4) 0.470(4) 0.070(12) Uiso 1 1 d . . .
H17 H 0.755(7) 0.237(6) 0.373(5) 0.099(16) Uiso 1 1 d . . .
H18 H 0.687(5) 0.350(5) 0.369(4) 0.072(12) Uiso 1 1 d . . .
H19 H 0.417(5) 0.130(4) 0.043(3) 0.048(9) Uiso 1 1 d . . .
H20 H 0.514(4) 0.278(4) 0.092(3) 0.057(10) Uiso 1 1 d . . .
H21 H 0.604(5) 0.175(4) 0.059(3) 0.052(9) Uiso 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Si Si 0.2541 0.3302
;
International Tables for Crystallography
(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
C15 Si1 C16 113.28(17) . . ?
C15 Si1 C14 106.72(18) . . ?
C16 Si1 C14 109.59(16) . . ?
C15 Si1 C12 113.20(16) . . ?
C16 Si1 C12 105.68(13) . . ?
C14 Si1 C12 108.28(16) . . ?
C8 N1 C1 124.5(2) . . ?
C8 N1 H7 115(2) . . ?
C1 N1 H7 120(2) . . ?
C11 N2 C8 115.8(2) . . ?
C9 N3 C8 116.0(2) . . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 N1 120.1(2) . . ?
C6 C1 N1 118.2(2) . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 C7 121.9(2) . . ?
C3 C2 C7 119.8(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H1 118(2) . . ?
C2 C3 H1 121(2) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H2 119(3) . . ?
C3 C4 H2 121(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H3 122(2) . . ?
C6 C5 H3 117(2) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C12 122.9(2) . . ?
C5 C6 C12 119.3(2) . . ?
C2 C7 H4 101(2) . . ?
C2 C7 H5 109(2) . . ?
H4 C7 H5 123(3) . . ?
C2 C7 H6 112(3) . . ?
H4 C7 H6 104(3) . . ?
H5 C7 H6 108(3) . . ?
N3 C8 N2 125.7(2) . . ?
N3 C8 N1 116.1(2) . . ?
N2 C8 N1 118.2(2) . . ?
N3 C9 C10 122.8(2) . . ?
N3 C9 H8 114(2) . . ?
C10 C9 H8 123(2) . . ?
C11 C10 C9 116.4(2) . . ?
C11 C10 H9 124(2) . . ?
C9 C10 H9 120(2) . . ?
N2 C11 C10 123.2(2) . . ?
N2 C11 H10 114.2(18) . . ?
C10 C11 H10 122.6(18) . . ?
C13 C12 C6 119.2(3) . . ?
C13 C12 Si1 119.4(3) . . ?
C6 C12 Si1 120.73(19) . . ?
C12 C13 H11 118(2) . . ?
C12 C13 H12 125(3) . . ?
H11 C13 H12 117(4) . . ?
Si1 C14 H13 112(2) . . ?
Si1 C14 H14 109(3) . . ?
H13 C14 H14 109(4) . . ?
Si1 C14 H15 108(3) . . ?
H13 C14 H15 116(3) . . ?
H14 C14 H15 104(4) . . ?
Si1 C15 H16 115(3) . . ?
Si1 C15 H17 107(3) . . ?
H16 C15 H17 104(4) . . ?
Si1 C15 H18 111(3) . . ?
H16 C15 H18 110(4) . . ?
H17 C15 H18 109(4) . . ?
Si1 C16 H19 112(2) . . ?
Si1 C16 H20 113(2) . . ?
H19 C16 H20 106(3) . . ?
Si1 C16 H21 112(2) . . ?
H19 C16 H21 107(3) . . ?
H20 C16 H21 107(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
Si1 C15 1.866(3) . ?
Si1 C16 1.872(3) . ?
Si1 C14 1.875(3) . ?
Si1 C12 1.895(3) . ?
N1 C8 1.353(3) . ?
N1 C1 1.427(3) . ?
N1 H7 0.76(3) . ?
N2 C11 1.333(3) . ?
N2 C8 1.352(3) . ?
N3 C9 1.337(3) . ?
N3 C8 1.350(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.399(4) . ?
C2 C7 1.510(4) . ?
C3 C4 1.375(5) . ?
C3 H1 0.99(3) . ?
C4 C5 1.374(5) . ?
C4 H2 0.91(4) . ?
C5 C6 1.404(4) . ?
C5 H3 1.07(5) . ?
C6 C12 1.490(4) . ?
C7 H4 1.05(4) . ?
C7 H5 1.03(4) . ?
C7 H6 1.01(5) . ?
C9 C10 1.382(4) . ?
C9 H8 0.95(3) . ?
C10 C11 1.379(4) . ?
C10 H9 0.94(4) . ?
C11 H10 0.93(3) . ?
C12 C13 1.336(4) . ?
C13 H11 0.88(4) . ?
C13 H12 0.96(5) . ?
C14 H13 0.98(4) . ?
C14 H14 0.74(5) . ?
C14 H15 1.03(5) . ?
C15 H16 0.93(4) . ?
C15 H17 0.90(6) . ?
C15 H18 0.92(5) . ?
C16 H19 0.88(4) . ?
C16 H20 0.95(4) . ?
C16 H21 0.96(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H7 N3 . . 2_666 2.954(3) 0.76(3) 2.19(3) 175(3) no
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
C8 N1 C1 C2 -62.3(3) . . . . ?
C8 N1 C1 C6 122.3(3) . . . . ?
C6 C1 C2 C3 -5.0(4) . . . . ?
N1 C1 C2 C3 179.7(2) . . . . ?
C6 C1 C2 C7 175.5(3) . . . . ?
N1 C1 C2 C7 0.3(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C7 C2 C3 C4 179.6(3) . . . . ?
C2 C3 C4 C5 4.4(5) . . . . ?
C3 C4 C5 C6 -4.1(5) . . . . ?
C2 C1 C6 C5 5.2(4) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C2 C1 C6 C12 -176.3(2) . . . . ?
N1 C1 C6 C12 -0.9(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C12 -179.1(3) . . . . ?
C9 N3 C8 N2 -2.8(4) . . . . ?
C9 N3 C8 N1 175.6(2) . . . . ?
C11 N2 C8 N3 2.8(4) . . . . ?
C11 N2 C8 N1 -175.6(2) . . . . ?
C1 N1 C8 N3 172.1(2) . . . . ?
C1 N1 C8 N2 -9.3(4) . . . . ?
C8 N3 C9 C10 0.9(4) . . . . ?
N3 C9 C10 C11 0.8(4) . . . . ?
C8 N2 C11 C10 -0.8(4) . . . . ?
C9 C10 C11 N2 -0.9(4) . . . . ?
C1 C6 C12 C13 122.2(3) . . . . ?
C5 C6 C12 C13 -59.3(4) . . . . ?
C1 C6 C12 Si1 -67.0(3) . . . . ?
C5 C6 C12 Si1 111.4(3) . . . . ?
C15 Si1 C12 C13 -86.9(3) . . . . ?
C16 Si1 C12 C13 148.6(3) . . . . ?
C14 Si1 C12 C13 31.2(3) . . . . ?
C15 Si1 C12 C6 102.4(2) . . . . ?
C16 Si1 C12 C6 -22.2(2) . . . . ?
C14 Si1 C12 C6 -139.5(2) . . . . ?
