Asymmetric Synthesis of Enantiomerically Pure Mono- and Binuclear Bis(cyclometalated) Iridium(III) Complexes.
Yao, Su-Yang; Ou, Yan-Ling; Ye, Bao-Hui; Inorganic chemistry 55 (2016) 6018–6026; doi:10.1021/acs.inorgchem.6b00527

data_4347724
_publ_section_title
;
 Asymmetric Synthesis of Enantiomerically Pure Mono- and Binuclear
 Bis(cyclometalated) Iridium(III) Complexes.
;
_journal_issue                   12
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6018
_journal_page_last               6026
_journal_paper_doi               10.1021/acs.inorgchem.6b00527
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C58 H40 Ir2 N8, 0.8(C H2 Cl2)'
_chemical_formula_sum            'C58.8 H41.6 Cl1.6 Ir2 N8'
_chemical_formula_weight         1301.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   31.1358(6)
_cell_length_b                   44.3487(8)
_cell_length_c                   20.5543(4)
_cell_measurement_reflns_used    24193
_cell_measurement_temperature    151(1)
_cell_measurement_theta_max      66.8760
_cell_measurement_theta_min      2.8930
_cell_volume                     28382.0(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      151(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega    0.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8494  -57.0000 -150.0000 70

  2 omega   58.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8494   38.0000 -180.0000 57

  3 omega  122.00  158.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -180.0000 36

  4 omega   64.00   91.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -180.0000 27

  5 omega   36.00   62.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 26

  6 omega   98.00  151.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   90.0000 53

  7 omega   71.00   97.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   30.0000 26

  8 omega   22.00   88.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -126.0000  -30.0000 66

  9 omega  122.00  164.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   30.0000 42

 10 omega   40.00   75.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   60.0000 35

 11 omega   28.00   69.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  120.0000 41

 12 omega   62.00  127.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -92.0000   -9.8796 65

 13 omega   30.00   62.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000   30.0000 32

 14 omega   89.00  114.00   1.0000   47.5000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000   23.9119 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0445094000
_diffrn_orient_matrix_UB_12      0.0152082000
_diffrn_orient_matrix_UB_13      0.0016325000
_diffrn_orient_matrix_UB_21      -0.0215649000
_diffrn_orient_matrix_UB_22      -0.0312186000
_diffrn_orient_matrix_UB_23      0.0023982000
_diffrn_orient_matrix_UB_31      0.0017062000
_diffrn_orient_matrix_UB_32      0.0006476000
_diffrn_orient_matrix_UB_33      0.0748971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            55272
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         2.762
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             12632
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         2.567
_refine_diff_density_min         -2.995
_refine_diff_density_rms         0.161
_refine_ls_abs_structure_details
;
 Flack x determined using 8764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.019(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1538
_refine_ls_number_reflns         23866
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0552
_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/[\s^2^(Fo^2^)+(0.0928P)^2^+119.4534P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                21406
_reflns_number_total             23866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b00527_si_004.cif
_cod_data_source_block           a
_cod_depositor_comments
;

2021-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C294 H208 Cl8 Ir10 N40 O0'
_cod_original_formula_weight         6506.59
_cod_original_formula_moiety         '5(C58 H40 Ir2 N8), 4(C H2 Cl2)'
_cod_original_formula_units_Z            4
_cod_database_code               4347724
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 98.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C164-Cl3 = C164-Cl4
 1.75 with sigma of 0.01
 Cl3-Cl4
 2.9 with sigma of 0.01
3. Rigid bond restraints
 C56, C57
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C39, C40
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N9, C60
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C78, C83
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C81, C82
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C79, C80
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N11, C62
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C159, C160
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C160, C161
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C67, C159
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N11, C162
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C85 \\sim C86 \\sim C87 \\sim C88: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C79) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(N13) \\sim Ueq, Uanis(N14)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C159) \\sim Ueq, Uanis(C158)
\\sim Ueq, Uanis(C160) \\sim Ueq, Uanis(C161) \\sim Ueq, Uanis(C162) \\sim Ueq,
Uanis(N11) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C81)
\\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C76) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C164(H16A,H16B), C163(H16C,H16D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C44(H44), C45(H45), C46(H46),
  C47(H47), C49(H49), C50(H50), C51(H51), C52(H52), C55(H55), C56(H56),
 C57(H57), C58(H58), C159(H159), C160(H160), C161(H161), C162(H162), C61(H61),
 C62(H62), C66(H66), C74(H74), C75(H75), C76(H76), C77(H77), C79(H79), C80(H80),
  C81(H81), C82(H82), C85(H85), C86(H86), C87(H87), C88(H88), C158(H158),
 C91(H91), C92(H92), C94(H94), C95(H95), C97(H97), C98(H98), C99(H99),
 C100(H100), C103(H103), C104(H104), C105(H105), C106(H106), C108(H108),
 C109(H109), C110(H110), C111(H111), C114(H114), C115(H115), C116(H116),
 C117(H117), C120(H120), C121(H121), C123(H123), C124(H124), C126(H126),
 C127(H127), C128(H128), C129(H129), C132(H132), C133(H133), C134(H134),
 C135(H135), C137(H137), C138(H138), C139(H139), C140(H140), C143(H143),
 C144(H144), C145(H145), C146(H146)
5.c Fitted hexagon refined as free rotating group:
 C31(C32,C33,C34,C35,C36), C53(C54,C55,C56,C57,C58), N11(C67,C159,C160,C161,
 C162), C72(C73,C74,C75,C76,C77)
;
_olex2_submission_special_instructions 'No special instructions were received'