Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration.
Gao, Tao-Tao; Zhang, Wen-Wen; Sun, Xin; Lu, Hou-Xiang; Li, Bi-Jie; Journal of the American Chemical Society 141 (2019) 4670–4677; doi:10.1021/jacs.8b13520

data_4128940
_publ_section_title
;
 Stereodivergent Synthesis through Catalytic Asymmetric Reversed
 Hydroboration.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4670
_journal_page_last               4677
_journal_paper_doi               10.1021/jacs.8b13520
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H14 Cl N O2'
_chemical_formula_sum            'C11 H14 Cl N O2'
_chemical_formula_weight         227.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.111(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8480(4)
_cell_length_b                   4.7553(2)
_cell_length_c                   11.5172(5)
_cell_measurement_reflns_used    2019
_cell_measurement_temperature    99.99(16)
_cell_measurement_theta_max      75.7570
_cell_measurement_theta_min      4.1030
_cell_volume                     554.25(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -112.00 -18.00   1.00    6.00    --  -40.81 -57.00-150.00   94
  2  \w    -98.00 -72.00   1.00    6.00    --  -40.81-134.00 -36.00   26
  3  \w    -92.00 -16.00   1.00    6.00    --  -40.81 -38.00 -90.00   76
  4  \w     55.00  81.00   1.00    6.00    --   40.81-134.00 -36.00   26
  5  \w     90.00 178.00   1.00   12.00    --  112.00  45.00-180.00   88
  6  \w     56.00  87.00   1.00   12.00    --  112.00-125.00  90.00   31
  7  \w     47.00 124.00   1.00   12.00    --  112.00 -45.00-150.00   77
  8  \w     40.00 139.00   1.00   12.00    --  112.00 -30.00   0.00   99
  9  \w     34.00  98.00   1.00   12.00    --  112.00 -95.00-150.00   64
 10  \w     31.00  71.00   1.00    6.00    --   40.81-136.00 144.00   40
 11  \w    -20.00  46.00   1.00    6.00    --   40.81 -38.00 -30.00   66
 12  \w     74.00 103.00   1.00    6.00    --   40.81-136.00 144.00   29
 13  \w      2.00  37.00   1.00    6.00    --   40.81 -99.00-180.00   35
 14  \w    102.00 153.00   1.00   12.00    --  111.58 125.00 120.00   51
 15  \w     63.00 115.00   1.00   12.00    --  111.58-125.00 150.00   52
 16  \w     96.00 132.00   1.00   12.00    --  111.58 -61.00 120.00   36
 17  \w     45.00  72.00   1.00   12.00    --  111.58 -61.00 120.00   27
 18  \w     93.00 162.00   1.00   12.00    --  111.58  45.00-120.00   69
 19  \w     66.00  92.00   1.00   12.00    --  111.58 -61.00-120.00   26
 20  \w     81.00 108.00   1.00   12.00    --  111.58-125.00  30.00   27
 21  \w     96.00 139.00   1.00   12.00    --  111.58  61.00 -60.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462206000
_diffrn_orient_matrix_UB_12      0.0021893000
_diffrn_orient_matrix_UB_13      -0.1431073000
_diffrn_orient_matrix_UB_21      0.1403753000
_diffrn_orient_matrix_UB_22      0.0824826000
_diffrn_orient_matrix_UB_23      0.0085647000
_diffrn_orient_matrix_UB_31      0.0365496000
_diffrn_orient_matrix_UB_32      -0.3133060000
_diffrn_orient_matrix_UB_33      0.0012761000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3274
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.496
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       needle
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(17)
_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     139
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0408P)^2^+0.0259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.518
_reflns_Friedel_fraction_full    0.674
_reflns_Friedel_fraction_max     0.674
_reflns_number_gt                1624
_reflns_number_total             1709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13520_si_002.cif
_cod_data_source_block           20180102gaotaotao
_cod_database_code               4128940
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C8(H8), C5(H5), C9(H9)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.758