Bis(mandelato)borate: an effective, inexpensive spiroborate anion for chiral resolution
Lawrence W-Y. Wong; Jack W-H. Kan; Thanh-ha Nguyen; Herman H-Y. Sung; Dang Li; Alex S-F. Au-Yeung; Rajpal Sharma; Zhenyang Lin; Ian D. Williams; Chem.Commun. 51 (2015) 15760–; doi:10.1039/C5cc04977F

data_7117977
_publ_section_title
;
 Bis(mandelato)borate: an effective, inexpensive spiroborate anion for
 chiral resolution
;
_journal_name_full               Chem.Commun.
_journal_page_first              15760
_journal_paper_doi               10.1039/C5cc04977F
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H26 N O4, C16 H12 B O6'
_chemical_formula_sum            'C37 H38 B N O10'
_chemical_formula_weight         667.49
_chemical_name_systematic        'Tetrahydropalmatinium Boron(bis-mandelate)'
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-09
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_audit_update_record
;
2015-03-02 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.596(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8770(3)
_cell_length_b                   13.3291(4)
_cell_length_c                   14.6644(4)
_cell_measurement_reflns_used    5500
_cell_measurement_temperature    172.9
_cell_measurement_theta_max      71.3321
_cell_measurement_theta_min      3.0452
_cell_volume                     1715.64(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      172.9
_diffrn_detector_area_resol_mean 15.9578
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -10.00   17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 27

  2 omega  -20.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  120.0000 45

  3 omega  -22.00    5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   39.0000   19.0000 27

  4 omega  -66.00  -39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 27

  5 omega  -34.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   87.0000   87.0000 50

  6 omega  -72.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  120.0000 44

  7 omega  -66.00  -39.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000  -38.0000  -60.0000 27

  8 omega   74.00  125.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  125.0000 -150.0000 51

  9 omega   32.00   58.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000   77.0000  -60.0000 26

 10 omega   84.00  124.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000   87.0000  -92.0000 40

 11 omega   79.00  122.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  125.0000   30.0000 43

 12 omega -134.00  -46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -50.0000  150.0000 88

 13 omega  -74.00    3.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   50.0000   30.0000 77

 14 omega  -69.00  -43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -52.0000  -88.0000 26

 15 omega  -68.00  -42.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -61.0000  -99.0000 26

 16 omega -133.00  -38.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -71.0000 -114.0000 95

 17 omega  -79.00  -48.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -59.0000 -109.0000 31

 18 omega  -68.00  -43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -50.0000  -60.0000 25

 19 omega   41.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000 -120.0000 26

 20 omega   40.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000    0.0000 29

 21 omega  132.00  158.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000 -120.0000 26

 22 omega   81.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  -60.0000 25

 23 omega   80.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000 -120.0000 30

 24 omega   37.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000 -150.0000 25

 25 omega   79.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   87.0000 -150.0000 25

 26 omega  109.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   87.0000 -150.0000 68

 27 omega   80.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  -90.0000 26

 28 omega   77.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   25.0000   30.0000 44

 29 omega  142.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   39.0000  -44.0000 26

 30 omega   81.00  169.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000    0.0000 88

 31 omega   97.00  124.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   50.0000  -30.0000 27

 32 omega  100.00  126.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   39.0000  -44.0000 26

 33 omega   79.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  111.0000  120.0000 98

 34 omega   88.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   50.0000 -120.0000 26

 35 omega   99.00  157.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   50.0000  -90.0000 58

 36 omega   80.00  166.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  111.0000   90.0000 86

 37 omega   37.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000 -120.0000 25

 38 omega   78.00  161.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   87.0000  -92.0000 83

 39 omega   89.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   50.0000    0.0000 27

 40 omega  128.00  164.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  -30.0000 36

 41 omega  153.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  111.0000   60.0000 25

 42 omega   76.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   25.0000    0.0000 38

 43 omega   80.00  125.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  111.0000   60.0000 45

 44 omega  144.00  169.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   25.0000   30.0000 25

 45 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  -30.0000 27
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0761181000
_diffrn_orient_matrix_UB_12      -0.0299922000
_diffrn_orient_matrix_UB_13      -0.0837532000
_diffrn_orient_matrix_UB_21      0.1502258000
_diffrn_orient_matrix_UB_22      0.0481960000
_diffrn_orient_matrix_UB_23      0.0456395000
_diffrn_orient_matrix_UB_31      0.0494182000
_diffrn_orient_matrix_UB_32      -0.1006743000
_diffrn_orient_matrix_UB_33      0.0468410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14049
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         3.05
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         6000
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                5357
_reflns_number_total             6000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04977f2.cif
_cod_data_source_block           lawr130
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7117977
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13