Silyl Phosphorus and Nitrogen Donor Chelates for Homogeneous Ortho Borylation Catalysis.
Ghaffari, Behnaz; Preshlock, Sean M.; Plattner, Donald L.; Staples, Richard J.; Maligres, Peter E.; Krska, Shane W.; Maleczka, Jr, Robert E; Smith, 3rd, Milton R; Journal of the American Chemical Society 136 (2014) 14345–; doi:10.1021/ja506229s

data_4122724
_publ_section_title
;
 Silyl Phosphorus and Nitrogen Donor Chelates for Homogeneous Ortho
 Borylation Catalysis.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14345
_journal_paper_doi               10.1021/ja506229s
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C34 H44 Ir P Si'
_chemical_formula_sum            'C34 H44 Ir P Si'
_chemical_formula_weight         703.95
_chemical_name_systematic
;
 ?
;
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                77.3150(10)
_cell_angle_beta                 86.7650(10)
_cell_angle_gamma                69.1190(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9128(11)
_cell_length_b                   10.2416(11)
_cell_length_c                   16.4821(18)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.634
_cell_measurement_theta_min      2.200
_cell_volume                     1524.8(3)
_computing_cell_refinement       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28194
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.190
_diffrn_reflns_theta_min         2.179
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.491
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0805 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8925. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       cube
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.073
_refine_diff_density_max         1.193
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5481
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0281P)^2^+8.3951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4702
_reflns_number_total             5481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja506229s_si_002.cif
_cod_data_source_block           iiibgsiir
_cod_depositor_comments
'Adding full bibliography for 4122723--4122724.cif.'
_cod_database_code               4122724
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.662
_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. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8: within 1.7A
with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C29(H29), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19),
 C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'