A synthetic and mechanistic investigation into the cobalt(i) catalyzed amination of aryl halides
Brennan, Marshall R.; Kim, Dongyoung; Fout, Alison R.; Chem. Sci. 5 (2014) 4831–; doi:10.1039/C4SC01257G

data_1553081
_publ_section_title
;
 A synthetic and mechanistic investigation into the cobalt(i) catalyzed
 amination of aryl halides
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              4831
_journal_paper_doi               10.1039/C4SC01257G
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C33 H44 Li N O3 Si'
_chemical_formula_sum            'C33 H44 Li N O3 Si'
_chemical_formula_weight         537.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7063(12)
_cell_length_b                   11.4184(7)
_cell_length_c                   13.9803(10)
_cell_measurement_temperature    100.02
_cell_volume                     2986.1(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II Duo Microfocus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            208451
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.586
_diffrn_reflns_theta_min         2.548
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  'THIS Is IN your .LST FIle'
_exptl_absorpt_correction_T_min  'This is In your .LST file'
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_recrystallization_method
'Grown from slow evaporation of concentrated THF solution at room temperature.'
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.369
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 4168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         9165
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.3685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0837
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                8854
_reflns_number_total             9165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc01257g2.cif
_cod_data_source_block           one
_cod_database_code               1553081
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C27) = Uanis(C27D)
Uanis(C28) = Uanis(C28D)
3. Others
 Sof(H26C)=Sof(H26D)=Sof(C28D)=Sof(H28C)=Sof(H28D)=Sof(C27D)=Sof(H27C)=
 Sof(H27D)=Sof(H29C)=Sof(H29D)=1-FVAR(1)
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H29A)=Sof(H29B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C26(H26C,H26D), C27(H27A,H27B), C28(H28A,H28B), C28D(H28C,H28D),
 C27D(H27C,H27D), C29(H29A,H29B), C29(H29C,H29D), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C33(H33A,H33B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_exptl_crystal_mounting_method 'Mounted on a cryoloop in paratone oil'