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_4086747
_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         'C39 H57 Cl2 N2 Ni P'
_chemical_formula_sum            'C39 H57 Cl2 N2 Ni P'
_chemical_formula_weight         714.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-15
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.505(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.050(3)
_cell_length_b                   14.103(3)
_cell_length_c                   14.527(3)
_cell_measurement_reflns_used    9543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.996
_cell_measurement_theta_min      4.426
_cell_volume                     3794.9(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.46
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            85883
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.638
_diffrn_reflns_theta_min         2.385
_exptl_absorpt_coefficient_mu    2.636
_exptl_absorpt_correction_T_max  0.9164
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0534 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.6858.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         7602
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0492P)^2^+2.3149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6672
_reflns_number_total             7602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00652_si_004.cif
_cod_data_source_block           schomaker58
_cod_depositor_comments
'Adding full bibliography for 4086747--4086749.cif.'
_cod_original_cell_volume        3794.8(12)
_cod_database_code               4086747
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.587
_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
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C24A) \\sim Ueq,
Uanis(C25A) \\sim Ueq, Uanis(C26A) \\sim Ueq, Uanis(C27A) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.05
3. Rigid body (RIGU) restrains
 C22, C23, C24, C25, C26, C27, C22A, C23A, C24A, C25A, C26A, C27A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{P1, C22A, C23A, C24A, C25A, C26A, C27A} sigma for 1-2: 0.02, 1-3: 0.04
as
{P1, C22, C23, C24, C25, C26, C27}
5. Others
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=
 Sof(H24D)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=
 Sof(C27A)=Sof(H27C)=Sof(H27D)=1-FVAR(1)
 Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C22(H22), C22A(H22A), C28(H28), C34(H34)
6.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C23A(H23C,H23D), C24A(H24C,H24D), C25A(H25C,H25D), C26A(H26C,H26D),
 C27A(H27C,H27D), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B),
 C38(H38A,H38B), C39(H39A,H39B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              31316
_shelx_hkl_checksum              23367
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id EET1174
_olex2_submission_special_instructions 'No special instructions were received'