Ruthenium-Catalyzed Selective Hydroboration of Nitriles and Imines.
Kaithal, Akash; Chatterjee, Basujit; Gunanathan, Chidambaram; The Journal of organic chemistry 81 (2016) 11153–11161; doi:10.1021/acs.joc.6b02122

data_4037390
_publ_section_title
;
 Ruthenium-Catalyzed Selective Hydroboration of Nitriles and Imines.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11153
_journal_page_last               11161
_journal_paper_doi               10.1021/acs.joc.6b02122
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H34 B2 Cl N O4'
_chemical_formula_sum            'C21 H34 B2 Cl N O4'
_chemical_formula_weight         421.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.920(2)
_cell_length_b                   12.260(3)
_cell_length_c                   15.790(3)
_cell_measurement_reflns_used    4095
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      2.38
_cell_volume                     2307.5(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.632
_diffrn_reflns_theta_min         2.103
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.7520.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0920P)^2^+0.0246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1513
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3431
_reflns_number_total             4294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02122_si_001.cif
_cod_data_source_block           try12
_cod_database_code               4037390
_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 Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00B(H00C,H00D), C00C(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00N(H00U), C00P(H00V)
2.c Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K), C00K(H00L,H00M,H00N), C00L(H00O,H00P,H00Q), C00M(H00R,
 H00S,H00T), C00Q(H00W,H00X,H00Y), C00R(H00Z,H,HA), C00S(H00,HB,HC), C00T(H0AA,
 HD,HE)
;
_shelx_res_checksum              40949
_shelx_hkl_checksum              3051
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'