A chiral spiroborate anion from diphenyl-l-tartramide [B{l-Tar(NHPh)2}2]−applied to some challenging resolutions
Wong, Lawrence W.-Y.; Tam, Gemma S.-S.; Chen, Xiaoyan; So, Frederick T.-K.; Soecipto, Aristyo; Sheong, Fu Kit; Sung, Herman H.-Y.; Lin, Zhenyang; Williams, Ian D.; CrystEngComm 20 (2018) 4831–; doi:10.1039/C8CE00855H

data_7231137
_publ_section_title
;
 A chiral spiroborate anion from diphenyl-l-tartramide
 [B{l-Tar(NHPh)2}2]&#x2212;applied to some challenging resolutions
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              4831
_journal_paper_doi               10.1039/C8CE00855H
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H28 B N4 O8, C9 H14 N'
_chemical_formula_sum            'C41 H42 B N5 O8'
_chemical_formula_weight         743.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-05-22 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.834(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.6200(11)
_cell_length_b                   5.25819(14)
_cell_length_c                   28.6090(9)
_cell_measurement_reflns_used    5835
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3100
_cell_measurement_theta_min      4.8120
_cell_volume                     3938.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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     89.00 178.00   1.00   50.00    --  110.57  45.00 120.00   89
  2  \w    -97.00  -3.00   1.00   20.00    --  -40.32 127.00 -47.00   94
  3  \w   -119.00 -13.00   1.00   20.00    --  -40.32 -77.00-120.00  106
  4  \w   -114.00 -12.00   1.00   20.00    --  -40.32 -57.00 120.00  102
  5  \w     41.00  96.00   1.00   50.00    --  110.57 -94.00  90.00   55
  6  \w     58.00 150.00   1.00   50.00    --  110.57 178.00  30.00   92
  7  \w     48.00 138.00   1.00   50.00    --  110.57 -45.00 120.00   90
  8  \w     87.00 176.00   1.00   50.00    --  110.57  45.00-180.00   89
  9  \w     32.00 112.00   1.00   50.00    --  110.57-111.00-180.00   80
 10  \w     32.00 111.00   1.00   50.00    --  110.57-111.00  30.00   79
 11  \w     34.00 137.00   1.00   50.00    --  110.57 -30.00   0.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0534828000
_diffrn_orient_matrix_UB_12      0.0275747000
_diffrn_orient_matrix_UB_13      0.0003514000
_diffrn_orient_matrix_UB_21      -0.0061979000
_diffrn_orient_matrix_UB_22      -0.2911971000
_diffrn_orient_matrix_UB_23      -0.0030086000
_diffrn_orient_matrix_UB_31      0.0238218000
_diffrn_orient_matrix_UB_32      -0.0152381000
_diffrn_orient_matrix_UB_33      0.0587713000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10916
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.446
_diffrn_reflns_theta_min         4.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.254
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2677 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         7008
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0577P)^2^+0.0193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                6488
_reflns_number_total             7008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00855h2.cif
_cod_data_source_block           lawr437cult
_cod_depositor_comments
'Adding full bibliography for 7231133--7231140.cif.'
_cod_database_code               7231137
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C20 N2 O6 B1'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.900
_reflns_odcompleteness_completeness 99.56
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O14A-C14
 1.2 with sigma of 0.02
3. Others
 Fixed Sof: N11(0.5) H11(0.5) O14(0.9) C42(0.5) H42(0.5) C41(0.5) C46(0.5)
 H46(0.5) C45(0.5) H45(0.5) C44(0.5) H44(0.5) C43(0.5) H43(0.5) N11A(0.5)
 H11A(0.5) O14A(0.1) C41A(0.5) C46A(0.5) H46A(0.5) C45A(0.5) H45A(0.5)
 C44A(0.5) H44A(0.5) C43A(0.5) H43A(0.5) C42A(0.5) H42A(0.5)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C63(H63)
4.b Secondary CH2 refined with riding coordinates:
 C62(H62A,H62B)
4.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
  N11(H11), C42(H42), C46(H46), C45(H45), C44(H44), C43(H43), N11A(H11A),
 C46A(H46A), C45A(H45A), C44A(H44A), C43A(H43A), C42A(H42A), C65(H65), C66(H66),
  C67(H67), C68(H68), C69(H69)
4.d Fitted hexagon refined as free rotating group:
 C42(C41,C46,C45,C44,C43), C41A(C46A,C45A,C44A,C43A,C42A)
4.e Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C)
;
_shelx_res_checksum              80045
_shelx_fab_checksum              54613
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.737