Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes.
Smith, James R.; Collins, Beatrice S. L.; Hesse, Matthew J.; Graham, Mark A.; Myers, Eddie L.; Aggarwal, Varinder K.; Journal of the American Chemical Society 139 (2017) 9148–9151; doi:10.1021/jacs.7b05149

data_4131418
_publ_section_title
;
 Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of
 Unactivated Terminal Alkenes.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9148
_journal_page_last               9151
_journal_paper_doi               10.1021/jacs.7b05149
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C15 H31 B2 N O4, C H2 Cl2'
_chemical_formula_sum            'C16 H33 B2 Cl2 N O4'
_chemical_formula_weight         395.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.100(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7825(6)
_cell_length_b                   11.3305(5)
_cell_length_c                   17.6140(9)
_cell_measurement_reflns_used    3132
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.32
_cell_volume                     2148.77(19)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_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  0.0483
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17213
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.811
_diffrn_reflns_theta_min         2.138
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0601 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.8885.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0402P)^2^+0.8179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3254
_reflns_number_total             4590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b05149_si_001.cif
_cod_data_source_block           testm1
_cod_database_code               4131418
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1A-Cl2A
 2.92 with sigma of 0.02
 Cl1A-C16 \\sim Cl1-C16
 with sigma of 0.01
 Cl1A-C16 \\sim Cl1-C16 \\sim Cl2A-C16 \\sim Cl2-C16
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl1A \\sim Cl1: within 1.7A with sigma of 0.003 and sigma for terminal atoms of
0.006
Cl2 \\sim Cl2A: within 1.7A with sigma of 0.003 and sigma for terminal atoms of
0.006
4. Others
 Fixed Sof: Cl1(0.92381) Cl2(0.92381) H16A(0.92381) H16B(0.92381)
 H16C(0.07619) H16D(0.07619) Cl1A(0.07619) Cl2A(0.07619)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B), C16(H16C,H16D)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              30059
_shelx_hkl_checksum              44042
_olex2_submission_special_instructions 'No special instructions were received'