Heteroleptic Nickel Complexes for the Markovnikov-Selective Hydroboration of Styrenes
Touney, Eric E.; Van Hoveln, Ryan; Buttke, Carl T.; Freidberg, Michael D.; Guzei, Ilia A.; Schomaker, Jennifer M.; Organometallics 35 (2016) 3436–; doi:10.1021/acs.organomet.6b00652

data_4086749
_publ_section_title
;
 Heteroleptic Nickel Complexes for the Markovnikov-Selective Hydroboration
 of Styrenes
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              3436
_journal_paper_doi               10.1021/acs.organomet.6b00652
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C87 H89 Cl2 N2 Ni P, 0.5(C8 H10)'
_chemical_formula_sum            'C93 H96.5 Cl2 N2 Ni P'
_chemical_formula_weight         1402.80
_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
_audit_creation_date             2015-06-24
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.06.08 svn.r3188 for OlexSys, GUI svn.r5058)
;
_cell_angle_alpha                106.004(16)
_cell_angle_beta                 95.015(18)
_cell_angle_gamma                96.289(15)
_cell_formula_units_Z            4
_cell_length_a                   13.613(4)
_cell_length_b                   23.589(7)
_cell_length_c                   24.661(7)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.173
_cell_volume                     7509(4)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2015.1-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\ \w and 0.5\ \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_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  0.0855
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            160626
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         0.866
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2982
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1753
_refine_ls_number_reflns         29504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0294P)^2^+6.2555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20613
_reflns_number_total             29504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00652_si_005.cif
_cod_data_source_block           schomaker59_sq
_cod_depositor_comments
'Adding full bibliography for 4086747--4086749.cif.'
_cod_original_formula_sum        'C93 H96.50 Cl2 N2 Ni P'
_cod_database_code               4086749
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.950
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C24(H24), C43(H43), C57(H57), C70(H70), C76(H76), C82(H82),
 C10A(H10A), C24A(H24A), C43A(H43A), C57A(H57A), C70A(H70A), C76A(H76A),
 C82A(H82A)
2.b Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,
 H75B), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B),
 C81(H81A,H81B), C83(H83A,H83B), C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B),
  C87(H87A,H87B), C71A(H71C,H71D), C72A(H72C,H72D), C73A(H73C,H73D), C74A(H74C,
 H74D), C75A(H75C,H75D), C77A(H77C,H77D), C78A(H78C,H78D), C79A(H79C,H79D),
 C80A(H80C,H80D), C81A(H81C,H81D), C83A(H83C,H83D), C84A(H84C,H84D), C85A(H85C,
 H85D), C86A(H86C,H86D), C87A(H87C,H87D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C39(H39), C41(H41), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49),
  C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C59(H59), C60(H60),
 C61(H61), C62(H62), C63(H63), C65(H65), C66(H66), C67(H67), C68(H68), C69(H69),
  C2A(H2A), C3A(H3A), C6A(H6A), C8A(H8A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A),
 C22A(H22A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A),
 C32A(H32A), C33A(H33A), C34A(H34A), C35A(H35A), C36A(H36A), C39A(H39A),
 C41A(H41A), C45A(H45A), C46A(H46A), C47A(H47A), C48A(H48A), C49A(H49A),
 C51A(H51A), C52A(H52A), C53A(H53A), C54A(H54A), C55A(H55A), C59A(H59A),
 C60A(H60A), C61A(H61A), C62A(H62A), C63A(H63A), C65A(H65A), C66A(H66A),
 C67A(H67A), C68A(H68A), C69A(H69A), C89(H89), C90(H90), C92(H92), C93(H93)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C56(H56A,H56B,H56C), C23A(H23D,H23E,H23F), C56A(H56D,
 H56E,H56F), C94(H94A,H94B,H94C), C95(H95A,H95B,H95C)
;
_shelx_res_checksum              9852
_shelx_hkl_checksum              4175
_shelx_fab_checksum              98764
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'