Extending N-heterocyclic carbene ligands into the third dimension: a new type of hybrid phosphazane/NHC system
Roth, Torsten; Vasilenko, Vladislav; Benson, Callum G. M.; Wadepohl, Hubert; Wright, Dominic S.; Gade, Lutz H.; Chem. Sci. 6 (2015) 2506–; doi:10.1039/C4SC03966A

data_1518730
_publ_section_title
;
 Extending N-heterocyclic carbene ligands into the third dimension: a new
 type of hybrid phosphazane/NHC system
;
_journal_issue                   4
_journal_name_full               'Chem. Sci.'
_journal_page_first              2506
_journal_paper_doi               10.1039/C4SC03966A
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C61 H68 Cl2 Ir2 N4 P2, C7 H8'
_chemical_formula_sum            'C71.5 H80 Cl2 Ir2 N4 P2'
_chemical_formula_weight         1512.13
_chemical_properties_physical    air-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_tro111
_audit_creation_date
;
'Mon Nov 03 11:34:00 2014'
;
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-19 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                66.4438(13)
_cell_angle_beta                 87.7181(11)
_cell_angle_gamma                64.8361(15)
_cell_formula_units_Z            2
_cell_length_a                   13.28816(19)
_cell_length_b                   15.4534(2)
_cell_length_c                   18.6095(2)
_cell_measurement_reflns_used    48927
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      31.1330
_cell_measurement_theta_min      3.4930
_cell_volume                     3131.28(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
  1 omega    7.00   34.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000   60.0000 54

  2 omega   31.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  150.0000 52

  3 omega    3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000 -150.0000 188

  4 omega    1.00   26.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000 -120.0000 50

  5 omega  -43.00   59.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -80.0000  104.2551 204

  6 omega   -3.00   25.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   79.0000  176.3817 56

  7 omega  -11.00   39.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   19.0000  120.0000 100

  8 omega   -3.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -60.0000 198

  9 omega   -3.00   88.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   60.0000 182

 10 omega    6.00   33.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000  150.0000 54

 11 omega   16.00   42.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000   30.0000 52

 12 omega  -42.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000 -180.0000 198

 13 omega    2.00   65.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000 -180.0000 126

 14 omega   74.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000 -180.0000 50

 15 omega   27.00   64.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   19.0000  -60.0000 74

 16 omega  -27.00   -1.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000    9.8157 52

 17 omega  -42.00   58.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -77.0000  -42.2681 200

 18 omega   22.00   58.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000    9.8157 72

 19 omega  -41.00   59.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -78.0000   59.2666 200

 20 omega  -42.00   60.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -80.0000 -101.1560 204

 21 omega    1.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000    0.0000 196

 22 omega   -3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -30.0000 200

 23 omega   -3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   90.0000 200

 24 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000  120.0000 180

 25 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000  -30.0000 180

 26 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000 -120.0000 180

 27 omega   -3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -60.0000 200

 28 omega   -4.00   25.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   79.0000  176.3817 58

 29 omega  -43.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  -30.0000 200

 30 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000 -180.0000 180

 31 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000   90.0000 180

 32 omega  -43.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000 -150.0000 200

 33 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000   30.0000 180

 34 omega  -17.00  100.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   19.0000  -90.0000 234

 35 omega  -43.00   58.50   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -80.0000 -101.1560 203

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0469787000
_diffrn_orient_matrix_UB_12      0.0092787000
_diffrn_orient_matrix_UB_13      0.0204136000
_diffrn_orient_matrix_UB_21      -0.0368429000
_diffrn_orient_matrix_UB_22      0.0271605000
_diffrn_orient_matrix_UB_23      -0.0366023000
_diffrn_orient_matrix_UB_31      0.0011853000
_diffrn_orient_matrix_UB_32      -0.0480518000
_diffrn_orient_matrix_UB_33      0.0040057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            205422
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.866
_diffrn_reflns_theta_min         3.215
_diffrn_source                   'microfocus X-Ray tube'
_exptl_absorpt_coefficient_mu    4.428
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_correction_T_min  0.535
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1509
_exptl_crystal_size_max          0.2014
_exptl_crystal_size_mid          0.1075
_exptl_crystal_size_min          0.0688
_refine_diff_density_max         2.121
_refine_diff_density_min         -1.727
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     698
_refine_ls_number_reflns         21933
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0408
_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/[\s^2^(Fo^2^)+(0.0260P)^2^+5.0636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18820
_reflns_number_total             21933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc03966a2.cif
_cod_data_source_block           ga_tro111_sq
_cod_depositor_comments
'Adding full bibliography for 1518727--1518731.cif.'
_cod_original_cell_volume        3131.27(9)
_cod_original_formula_sum        'C71.50 H80 Cl2 Ir2 N4 P2'
_cod_database_code               1518730
_audit_block_refno               2231
_audit_block_usercomment         'tr1478B orange irregular'
_shelx_estimated_absorpt_t_max   0.666
_shelx_estimated_absorpt_t_min   0.666
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C71, C72, C73, C74, C75, C76, C77
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C20(H20), C33(H33), C46(H46), C47(H47), C50(H50), C51(H51), C54(H54),
 C55(H55), C58(H58), C59(H59)
3.b Secondary CH2 refined with riding coordinates:
 C48(H48A,H48B), C49(H49A,H49B), C52(H52A,H52B), C53(H53A,H53B), C56(H56A,
 H56B), C57(H57A,H57B), C60(H60A,H60B), C61(H61A,H61B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C13(H13), C15(H15), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C35(H35), C36(H36),
  C37(H37), C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44),
 C45(H45), C72(H72), C73(H73), C74(H74), C75(H75), C76(H76)
3.d Fitted hexagon refined as free rotating group:
 C71(C72,C73,C74,C75,C76)
3.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C77(H77A,H77B,H77C)
;
_shelx_res_checksum              24324
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            13.28816(19)
_cell_oxdiff_length_b            15.4534(2)
_cell_oxdiff_length_c            18.6094(2)
_cell_oxdiff_angle_alpha         66.4438(13)
_cell_oxdiff_angle_beta          87.7181(11)
_cell_oxdiff_angle_gamma         64.8361(15)
_cell_oxdiff_volume              3131.27(7)
_cell_oxdiff_measurement_reflns_used 48927
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_theta     26.32
_reflns_odcompleteness_iscentric 1
_platon_squeeze_void_probe_radius 1.20