A modular approach to neutral P,N-ligands: synthesis and coordination chemistry.
Vasilenko, Vladislav; Roth, Torsten; Blasius, Clemens K.; Intorp, Sebastian N.; Wadepohl, Hubert; Gade, Lutz H.; Beilstein journal of organic chemistry 12 (2016) 846–853; doi:10.3762/bjoc.12.83

data_4031980
_publ_section_title
;
 A modular approach to neutral P,N-ligands: synthesis and coordination
 chemistry.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              846
_journal_page_last               853
_journal_paper_doi               10.3762/bjoc.12.83
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety
'C45 H57 Ir N2 P, 0.5(C7 H8), B F4, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C49 H62 B Cl F4 Ir N2 P'
_chemical_formula_weight         1024.43
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_vv11
_audit_creation_date
;
'Fri Feb 06 16:47:22 2015'
;
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record             '06.02.2015 16:55:24 CET UTC+01:00  encif 1.29'
_cell_angle_alpha                107.7617(5)
_cell_angle_beta                 95.9466(5)
_cell_angle_gamma                96.1981(5)
_cell_formula_units_Z            4
_cell_length_a                   10.95376(6)
_cell_length_b                   17.76136(11)
_cell_length_c                   24.90835(15)
_cell_measurement_reflns_used    135729
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      32.0210
_cell_measurement_theta_min      3.6200
_cell_volume                     4540.08(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_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    'SHELXT (Sheldrick, 2013)'
_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 0.946
_diffrn_measurement_details
;
  1 omega  -44.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -80.0000   12.6110 202

  2 omega  -44.00   59.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -80.0000   84.9032 206

  3 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   57.0000  120.0000 180

  4 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   57.0000  -60.0000 180

  5 omega   -3.00   39.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000  150.0000 84

  6 omega   59.00   85.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000  150.0000 52

  7 omega  -43.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -77.0000 -180.0000 200

  8 omega   -3.00   82.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000   30.0000 170

  9 omega   -2.00   82.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000 -150.0000 168

 10 omega   -2.00   35.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000  -30.0000 74

 11 omega   58.00   94.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000  -30.0000 72

 12 omega  -43.00   60.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -80.0000  -97.4181 206

 13 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -57.0000 -150.0000 180

 14 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   57.0000    0.0000 180

 15 omega   -3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000 -150.0000 200

 16 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -57.0000  -90.0000 180

 17 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   57.0000   60.0000 180

 18 omega   -3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000  120.0000 200

 19 omega   -5.00   24.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   80.0000  -66.7434 58

 20 omega  -42.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -57.0000   90.0000 180

 21 omega    1.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   38.0000  -90.0000 196

 22 omega  -43.00   60.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -80.0000  126.9174 206

 23 omega  -44.00   59.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -80.0000   38.7341 206

 24 omega  -43.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -77.0000  -30.0000 200

 25 omega    1.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   38.0000 -180.0000 196

 26 omega  -43.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -77.0000 -180.0000 200

 27 omega   -3.00   97.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   77.0000    0.0000 200

 28 omega    6.00   96.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   57.0000  -90.0000 180

 29 omega  -43.00   57.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -77.0000 -150.0000 200

 30 omega  -44.00   59.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881  -80.0000   12.6110 206

 31 omega  -46.00  100.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881    0.0000    0.0000 292

 32 omega  -43.00   60.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -80.0000  -97.4181 206

 33 omega  -46.00  100.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881    0.0000  240.0000 292

 34 omega  -45.00  100.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881    9.0000   89.0000 290

 35 omega  -46.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   -9.0000  -84.0000 290

 36 omega  -45.00  100.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881    9.0000   89.0000 290

 37 omega  -46.00   99.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881   -9.0000  -84.0000 290

 38 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   26.7881    0.0000     -     240

 39 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -20.0000     -     240

 40 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   20.0000     -     240

 41 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -40.0000     -     240

 42 omega  -46.00  100.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7881    0.0000  120.0000 292

 43 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -60.0000     -     240

 44 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   60.0000     -     240

 45 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   26.7881    0.0000     -     240

 46 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -20.0000     -     240

 47 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   20.0000     -     240

 48 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -40.0000     -     240

 49 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   40.0000     -     240

 50 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -60.0000     -     240

 51 phi    120.00  240.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   60.0000     -     240

 52 phi      0.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   40.0000     -     240

 53 phi    240.00  360.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -20.0000     -     240

 54 phi    240.00  360.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881   20.0000     -     240

 55 phi    240.00  337.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  26.7881   26.7881  -40.0000     -     194

 56 phi    240.00  360.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   26.7881    0.0000     -     240

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      0.0009162000
_diffrn_orient_matrix_UB_12      -0.0234220000
_diffrn_orient_matrix_UB_13      -0.0286304000
_diffrn_orient_matrix_UB_21      0.0657749000
_diffrn_orient_matrix_UB_22      0.0053367000
_diffrn_orient_matrix_UB_23      0.0050525000
_diffrn_orient_matrix_UB_31      -0.0023370000
_diffrn_orient_matrix_UB_32      -0.0349343000
_diffrn_orient_matrix_UB_33      0.0082386000
_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  0.0740
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            658461
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.888
_diffrn_reflns_theta_min         3.208
_diffrn_source                   'microfocus X-Ray tube'
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.083
_refine_diff_density_max         1.631
_refine_diff_density_min         -1.997
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1096
_refine_ls_number_reflns         32099
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0087P)^2^+12.5319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.000
_reflns_number_gt                29136
_reflns_number_total             32099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-83-S2.cif
_cod_data_source_block           ga_vv11
_cod_depositor_comments
'Adding full bibliography for 4031975--4031986.cif.'
_cod_database_code               4031980
_audit_block_refno               2342
_audit_block_usercomment         'VV111, block, red'
_chemical_oxdiff_formula         'C49 H62 B1 Cl1 F4 Ir1 N2 P1'
_chemical_oxdiff_usercomment     'VV111, block, red'
_shelx_estimated_absorpt_t_max   0.748
_shelx_estimated_absorpt_t_min   0.748
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_shelxl_version_number           2014/7
_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. Restrained distances
 F11-F12 \\sim F11-F13 \\sim F11-F14 \\sim F12-F13 \\sim F12-F14 \\sim F13-F14
\\sim F51-F52 \\sim F51-F53
 \\sim F51-F54 \\sim F52-F53 \\sim F52-F54 \\sim F53-F54
 with sigma of 0.02
 B1-F11 \\sim B1-F12 \\sim B1-F13 \\sim B1-F14 \\sim B51-F51 \\sim B51-F52
\\sim B51-F53 \\sim B51-F54
 with sigma of 0.02
 C201-Cl1 \\sim C201-Cl2 \\sim C202-Cl1 \\sim C202-Cl2
 with sigma of 0.02
3. Others
 Sof(C202)=Sof(H20C)=Sof(H20D)=1-FVAR(1)
 Sof(C201)=Sof(H20A)=Sof(H20B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C20(H20), C23(H23), C38(H38), C39(H39), C42(H42), C43(H43),
 C58(H58), C61(H61), C70(H70), C73(H73), C88(H88), C89(H89), C92(H92), C93(H93)
4.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C41(H41A,H41B), C44(H44A,H44B), C45(H45A,H45B), C90(H90A,
 H90B), C91(H91A,H91B), C94(H94A,H94B), C95(H95A,H95B), C201(H20A,H20B),
 C202(H20C,H20D)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18), C27(H27), C28(H28),
 C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
  C54(H54), C55(H55), C56(H56), C66(H66), C67(H67), C68(H68), C77(H77),
 C78(H78), C79(H79), C80(H80), C81(H81), C83(H83), C84(H84), C85(H85), C86(H86),
  C87(H87), C102(H102), C103(H103), C104(H104), C105(H105), C106(H106)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C),
 C63(H63A,H63B,H63C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C74(H74A,H74B,
 H74C), C75(H75A,H75B,H75C), C107(H10D,H10E,H10F)
;
_shelx_res_checksum              46204
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            10.95376(6)
_cell_oxdiff_length_b            17.76136(11)
_cell_oxdiff_length_c            24.90835(15)
_cell_oxdiff_angle_alpha         107.7617(5)
_cell_oxdiff_angle_beta          95.9466(5)
_cell_oxdiff_angle_gamma         96.1981(5)
_cell_oxdiff_volume              4540.08(4)
_cell_oxdiff_measurement_reflns_used 135729