#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:48:35 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/77/4517778.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_4517778
loop_
_publ_author_name
'Liu, Wentan'
'Yang, Wu'
'Zhu, Jiefeng'
'Guo, Yonghong'
'Wang, Na'
'Ke, Jie'
'Yu, Peiyuan'
'He, Chuan'
_publ_section_title
;
 Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C--H Amidation for
 the Synthesis of Chiral Sulfoxides
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              7207
_journal_page_last               7215
_journal_paper_doi               10.1021/acscatal.0c02109
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C26 H42 Cl4 Ir2'
_chemical_formula_sum            'C26 H42 Cl4 Ir2'
_chemical_formula_weight         880.79
_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             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.865(2)
_cell_angle_beta                 98.989(2)
_cell_angle_gamma                100.722(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3494(5)
_cell_length_b                   9.1549(6)
_cell_length_c                   9.6175(6)
_cell_measurement_reflns_used    9769
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      2.34
_cell_volume                     689.02(8)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23290
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.611
_diffrn_reflns_theta_min         2.220
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.049
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1728 before and 0.1028 after correction. The Ratio of minimum to maximum transmission is 0.2774. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         3.959
_refine_diff_density_min         -2.123
_refine_diff_density_rms         0.282
_refine_ls_extinction_coef       0.0081(10)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0313
_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)+(0.0497P)²+3.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4117
_reflns_number_total             4221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c02109_si_004.cif
_cod_data_source_block           cxy0934_0m
_cod_depositor_comments
;Adding full bibliography for 4517774--4517778.cif.

 Adding full bibliography for 4517774--4517778.cif.
;
_cod_database_code               4517778
_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   0.165
_shelx_estimated_absorpt_t_min   0.147
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Ir1 Ir 0.31651(2) 0.40021(2) 0.84971(2) 0.00795(8) Uani 1 1 d . . . . .
Cl2 Cl 0.30398(14) 0.64709(12) 0.81126(12) 0.0152(2) Uani 1 1 d . . . . .
Cl1 Cl 0.61919(13) 0.47993(13) 0.88691(11) 0.01297(19) Uani 1 1 d . . . . .
C2 C 0.0876(5) 0.2805(5) 0.6996(5) 0.0106(7) Uani 1 1 d . . . . .
C11 C 0.2046(8) 0.0661(6) 0.4007(5) 0.0210(10) Uani 1 1 d . . . . .
H11A H 0.082813 0.042336 0.386136 0.032 Uiso 1 1 calc GR . . . .
H11B H 0.248343 -0.007183 0.447470 0.032 Uiso 1 1 calc GR . . . .
H11C H 0.237112 0.058565 0.306248 0.032 Uiso 1 1 calc GR . . . .
C1 C 0.2292(5) 0.2326(5) 0.6463(5) 0.0100(7) Uani 1 1 d . . . . .
C5 C 0.3049(5) 0.1600(5) 0.7539(5) 0.0109(7) Uani 1 1 d . . . . .
C3 C 0.0849(5) 0.2495(5) 0.8398(5) 0.0116(7) Uani 1 1 d . . . . .
C7 C 0.2556(7) 0.1115(6) 1.0016(5) 0.0187(9) Uani 1 1 d . . . . .
H7A H 0.177911 0.133997 1.065613 0.028 Uiso 1 1 calc GR . . . .
H7B H 0.369925 0.161153 1.054435 0.028 Uiso 1 1 calc GR . . . .
H7C H 0.244134 -0.000024 0.970323 0.028 Uiso 1 1 calc GR . . . .
C10 C 0.2759(6) 0.2303(5) 0.4985(5) 0.0136(8) Uani 1 1 d . . . . .
C12 C 0.2025(7) 0.3423(6) 0.4243(5) 0.0211(10) Uani 1 1 d . . . . .
H12A H 0.081168 0.305800 0.395398 0.032 Uiso 1 1 calc GR . . . .
H12B H 0.249133 0.347924 0.337674 0.032 Uiso 1 1 calc GR . . . .
H12C H 0.230476 0.444780 0.492397 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.4648(7) 0.2751(7) 0.5109(6) 0.0229(10) Uani 1 1 d . . . . .
H13A H 0.488778 0.276111 0.414497 0.034 Uiso 1 1 calc GR . . . .
H13B H 0.516647 0.200246 0.548447 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.509667 0.377780 0.577590 0.034 Uiso 1 1 calc GR . . . .
C6 C 0.4466(6) 0.0810(6) 0.7532(6) 0.0189(9) Uani 1 1 d . . . . .
H6A H 0.461138 0.039786 0.838837 0.028 Uiso 1 1 calc GR . . . .
H6B H 0.548985 0.154978 0.755668 0.028 Uiso 1 1 calc GR . . . .
H6C H 0.422549 -0.003409 0.664464 0.028 Uiso 1 1 calc GR . . . .
C8 C -0.0379(6) 0.2793(6) 0.9335(6) 0.0171(9) Uani 1 1 d . . . . .
H8A H -0.072316 0.373855 0.924098 0.026 Uiso 1 1 calc GR . . . .
H8B H 0.013461 0.290872 1.035405 0.026 Uiso 1 1 calc GR . . . .
H8C H -0.135506 0.192653 0.902709 0.026 Uiso 1 1 calc GR . . . .
C4 C 0.2171(6) 0.1717(5) 0.8709(5) 0.0124(8) Uani 1 1 d . . . . .
C9 C -0.0392(6) 0.3545(6) 0.6304(5) 0.0157(8) Uani 1 1 d . . . . .
H9A H 0.018028 0.441265 0.599011 0.024 Uiso 1 1 calc GR . . . .
H9B H -0.104453 0.391667 0.701333 0.024 Uiso 1 1 calc GR . . . .
H9C H -0.113626 0.278720 0.545696 0.024 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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
Cl2 Ir1 Cl1 87.68(4) . . ?
Cl2 Ir1 Cl1 88.33(4) . 2_667 ?
Cl1 Ir1 Cl1 80.92(4) . 2_667 ?
C2 Ir1 Cl2 95.13(12) . . ?
C2 Ir1 Cl1 146.69(12) . . ?
C2 Ir1 Cl1 132.26(12) . 2_667 ?
C2 Ir1 C5 65.89(17) . . ?
C2 Ir1 C4 65.57(17) . . ?
C1 Ir1 Cl2 108.47(12) . . ?
C1 Ir1 Cl1 161.03(12) . 2_667 ?
C1 Ir1 Cl1 107.82(12) . . ?
C1 Ir1 C2 40.05(16) . . ?
C1 Ir1 C5 40.18(16) . . ?
C1 Ir1 C3 67.44(17) . . ?
C1 Ir1 C4 66.69(17) . . ?
C5 Ir1 Cl2 147.51(12) . . ?
C5 Ir1 Cl1 124.08(12) . 2_667 ?
C5 Ir1 Cl1 94.76(12) . . ?
C5 Ir1 C4 38.56(16) . . ?
C3 Ir1 Cl2 116.53(12) . . ?
C3 Ir1 Cl1 155.75(12) . . ?
C3 Ir1 Cl1 97.52(13) . 2_667 ?
C3 Ir1 C2 39.43(16) . . ?
C3 Ir1 C5 65.89(17) . . ?
C3 Ir1 C4 39.36(17) . . ?
C4 Ir1 Cl2 155.90(13) . . ?
C4 Ir1 Cl1 94.36(12) . 2_667 ?
C4 Ir1 Cl1 116.41(13) . . ?
Ir1 Cl1 Ir1 99.08(4) . 2_667 ?
C1 C2 Ir1 69.3(2) . . ?
C1 C2 C9 129.2(4) . . ?
C3 C2 Ir1 69.9(2) . . ?
C3 C2 C1 109.0(4) . . ?
C3 C2 C9 121.8(4) . . ?
C9 C2 Ir1 125.7(3) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C2 C1 Ir1 70.7(2) . . ?
C2 C1 C5 105.9(4) . . ?
C2 C1 C10 128.4(4) . . ?
C5 C1 Ir1 71.4(2) . . ?
C5 C1 C10 124.9(4) . . ?
C10 C1 Ir1 130.3(3) . . ?
C1 C5 Ir1 68.5(2) . . ?
C1 C5 C6 130.3(4) . . ?
C6 C5 Ir1 127.5(3) . . ?
C4 C5 Ir1 70.9(3) . . ?
C4 C5 C1 108.7(4) . . ?
C4 C5 C6 121.0(4) . . ?
C2 C3 Ir1 70.7(2) . . ?
C2 C3 C8 127.3(4) . . ?
C2 C3 C4 107.7(4) . . ?
C8 C3 Ir1 126.6(3) . . ?
C4 C3 Ir1 71.7(3) . . ?
C4 C3 C8 124.8(4) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
C11 C10 C12 108.4(4) . . ?
C1 C10 C11 107.0(4) . . ?
C1 C10 C12 112.7(4) . . ?
C1 C10 C13 112.3(4) . . ?
C13 C10 C11 110.2(4) . . ?
C13 C10 C12 106.3(4) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 Ir1 70.6(2) . . ?
C5 C4 C3 108.5(4) . . ?
C5 C4 C7 125.2(4) . . ?
C3 C4 Ir1 68.9(2) . . ?
C3 C4 C7 126.3(4) . . ?
C7 C4 Ir1 126.9(3) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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
Ir1 Cl2 2.3883(11) . ?
Ir1 Cl1 2.4417(10) . ?
Ir1 Cl1 2.4550(10) 2_667 ?
Ir1 C2 2.143(4) . ?
Ir1 C1 2.125(4) . ?
Ir1 C5 2.165(4) . ?
Ir1 C3 2.132(4) . ?
Ir1 C4 2.169(4) . ?
C2 C1 1.461(6) . ?
C2 C3 1.442(6) . ?
C2 C9 1.507(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.536(7) . ?
C1 C5 1.474(6) . ?
C1 C10 1.528(6) . ?
C5 C6 1.497(6) . ?
C5 C4 1.431(6) . ?
C3 C8 1.490(6) . ?
C3 C4 1.449(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C4 1.495(6) . ?
C10 C12 1.536(7) . ?
C10 C13 1.532(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
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
Ir1 C2 C1 C5 63.1(3) . . . . ?
Ir1 C2 C1 C10 -126.6(5) . . . . ?
Ir1 C2 C3 C8 121.9(5) . . . . ?
Ir1 C2 C3 C4 -62.5(3) . . . . ?
Ir1 C1 C5 C6 -121.5(5) . . . . ?
Ir1 C1 C5 C4 59.6(3) . . . . ?
Ir1 C1 C10 C11 167.3(4) . . . . ?
Ir1 C1 C10 C12 -73.7(5) . . . . ?
Ir1 C1 C10 C13 46.3(6) . . . . ?
Ir1 C5 C4 C3 58.7(3) . . . . ?
Ir1 C5 C4 C7 -122.0(5) . . . . ?
Ir1 C3 C4 C5 -59.7(3) . . . . ?
Ir1 C3 C4 C7 121.0(5) . . . . ?
C2 C1 C5 Ir1 -62.6(3) . . . . ?
C2 C1 C5 C6 175.9(5) . . . . ?
C2 C1 C5 C4 -3.0(5) . . . . ?
C2 C1 C10 C11 -95.9(5) . . . . ?
C2 C1 C10 C12 23.1(7) . . . . ?
C2 C1 C10 C13 143.1(5) . . . . ?
C2 C3 C4 Ir1 61.9(3) . . . . ?
C2 C3 C4 C5 2.2(5) . . . . ?
C2 C3 C4 C7 -177.1(4) . . . . ?
C1 C2 C3 Ir1 58.4(3) . . . . ?
C1 C2 C3 C8 -179.7(4) . . . . ?
C1 C2 C3 C4 -4.1(5) . . . . ?
C1 C5 C4 Ir1 -58.1(3) . . . . ?
C1 C5 C4 C3 0.6(5) . . . . ?
C1 C5 C4 C7 179.9(4) . . . . ?
C5 C1 C10 C11 72.7(6) . . . . ?
C5 C1 C10 C12 -168.3(4) . . . . ?
C5 C1 C10 C13 -48.4(6) . . . . ?
C3 C2 C1 Ir1 -58.7(3) . . . . ?
C3 C2 C1 C5 4.4(5) . . . . ?
C3 C2 C1 C10 174.6(4) . . . . ?
C10 C1 C5 Ir1 126.7(4) . . . . ?
C10 C1 C5 C6 5.2(8) . . . . ?
C10 C1 C5 C4 -173.7(4) . . . . ?
C6 C5 C4 Ir1 122.9(4) . . . . ?
C6 C5 C4 C3 -178.4(4) . . . . ?
C6 C5 C4 C7 0.9(7) . . . . ?
C8 C3 C4 Ir1 -122.4(5) . . . . ?
C8 C3 C4 C5 177.9(4) . . . . ?
C8 C3 C4 C7 -1.4(7) . . . . ?
C9 C2 C1 Ir1 119.8(5) . . . . ?
C9 C2 C1 C5 -177.1(4) . . . . ?
C9 C2 C1 C10 -6.8(8) . . . . ?
C9 C2 C3 Ir1 -120.3(4) . . . . ?
C9 C2 C3 C8 1.6(7) . . . . ?
C9 C2 C3 C4 177.2(4) . . . . ?
