Catalytic asymmetric synthesis of carboranylated diols bearing two adjacent stereocenters located at the α,β-position of <i>o</i>-carborane cage carbon.
Duan, Hui-Xin; Li, Hao-Nan; Yang, Yong; Wu, Xiao-Jun; Wang, You-Qing; Dalton transactions (Cambridge, England : 2003)  (2023) –; doi:10.1039/d3dt00129f

data_7712527
_publ_section_title
;
 Catalytic asymmetric synthesis of carboranylated diols bearing two
 adjacent stereocenters located at the &#x3b1;,&#x3b2;-position of
 <i>o</i>-carborane cage carbon.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt00129f
_journal_year                    2023
_chemical_formula_moiety         'C10 H19 B10 Cl O2'
_chemical_formula_sum            'C10 H19 B10 Cl O2'
_chemical_formula_weight         314.80
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-03 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4579(4)
_cell_length_b                   12.7488(5)
_cell_length_c                   13.7855(5)
_cell_measurement_reflns_used    2112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4880
_cell_measurement_theta_min      4.7000
_cell_volume                     1662.21(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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    -59.00 -12.00   1.00    1.00    --  -33.50 -37.00 -90.00   47
  2  \w    -87.00 -19.00   1.00    1.00    --  -33.50 -57.00  60.00   68
  3  \w     36.00  64.00   1.00    1.00    --   36.47 -77.00  60.00   28
  4  \w     63.00 107.00   1.00    1.00    --   36.47 178.00  90.00   44
  5  \w     61.00  95.00   1.00    1.00    --   36.47  57.00-150.00   34
  6  \w     42.00 124.00   1.00    5.00    --  108.00 -61.00 -90.00   82
  7  \w    109.00 177.00   1.00    5.00    --  108.00  45.00-120.00   68
  8  \w     40.00  98.00   1.00    5.00    --  108.00 -94.00 120.00   58
  9  \w     95.00 132.00   1.00    5.00    --  108.00 -30.00  90.00   37
 10  \w     38.00  64.00   1.00    5.00    --  108.00 -30.00  90.00   26
 11  \w     68.00  96.00   1.00    5.00    --  108.00 -94.00-180.00   28
 12  \w    -93.00 -66.00   1.00    1.00    --  -33.50 -37.00   0.00   27
 13  \w     13.00  69.00   1.00    1.00    --   36.47 -99.00-150.00   56
 14  \w     80.00 106.00   1.00    1.00    --   36.47 178.00-180.00   26
 15  \w     66.00 116.00   1.00    3.00    --  108.00 178.00 -30.00   50
 16  \w     84.00 147.00   1.00    3.00    --  108.00 178.00-180.00   63
 17  \w     78.00 104.00   1.00    3.00    --  108.00 -94.00-180.00   26
 18  \w     91.00 161.00   1.00    3.00    --  108.00  61.00 -30.00   70
 19  \w     69.00  95.00   1.00    3.00    --  108.00 178.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0799985000
_diffrn_orient_matrix_UB_12      -0.0960574000
_diffrn_orient_matrix_UB_13      0.0397048000
_diffrn_orient_matrix_UB_21      0.1127812000
_diffrn_orient_matrix_UB_22      -0.0729289000
_diffrn_orient_matrix_UB_23      -0.0441167000
_diffrn_orient_matrix_UB_31      0.0860631000
_diffrn_orient_matrix_UB_32      0.0062781000
_diffrn_orient_matrix_UB_33      0.0947799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.096
_diffrn_reflns_theta_min         4.724
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(15)
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0716P)^2^+0.0758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2772
_reflns_number_total             3145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00129f2.cif
_cod_data_source_block           20210108
_cod_original_cell_volume        1662.21(12)
_cod_database_code               7712527
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N4Cl1B8
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.828
_shelx_estimated_absorpt_t_min   0.744
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H1-O1
 0.9 with sigma of 0.02
 O2-H2
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
3.c Boron cage BH refined with riding coordinates:
 C2(H2A), B1(H1A), B2(H2B), B3(H3A), B4(H4A), B5(H5), B6(H6A), B7(H7A), B8(H8),
  B9(H9A), B10(H10A)
;
_shelx_res_checksum              94955
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.931