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_7117980
_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         'C18 H18 B Na O7'
_chemical_formula_sum            'C18 H18 B Na O7'
_chemical_formula_weight         380.12
_chemical_name_systematic        'Sodium Bora(bis-mandelate) ethanolate'
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-03-17 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                87.1166(18)
_cell_angle_beta                 88.9874(16)
_cell_angle_gamma                81.7319(19)
_cell_formula_units_Z            4
_cell_length_a                   9.27390(19)
_cell_length_b                   13.4321(3)
_cell_length_c                   14.8221(3)
_cell_measurement_reflns_used    18082
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.3810
_cell_measurement_theta_min      4.5700
_cell_volume                     1824.75(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   27.00  107.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -60.0000 80

  2 omega  -32.00   67.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8828  -57.0000    0.0000 99

  3 omega   23.00   97.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8828 -125.0000  -90.0000 74

  4 omega   73.00  114.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -103.0000 41

  5 omega   57.00   98.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 41

  6 omega   42.00  108.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   30.0000 66

  7 omega   43.00  134.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  120.0000 91

  8 omega  107.00  134.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   59.0000   40.4825 27

  9 omega  122.00  148.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000    0.0000 26

 10 omega  113.00  157.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   77.0000  -66.0988 44

 11 omega  135.00  161.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000 -120.0000 26

 12 omega  124.00  177.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -150.0000 53

 13 omega  108.00  176.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -180.0000 68

 14 omega   81.00  121.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000 -120.0000 40

 15 omega   80.00  177.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000  -90.0000 97

 16 omega   94.00  121.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000   49.0744 27

 17 omega   83.00  146.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000   69.6981 63

 18 omega  135.00  163.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   64.0000  120.4477 28

 19 omega   81.00  156.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000   60.0000 75

 20 omega   77.00  173.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000  -30.0000 96

 21 omega   81.00  178.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000   30.0000 97

 22 omega   80.00  178.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000   90.0000 98

 23 omega   78.00  103.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000    0.0000 25

 24 omega   65.00  119.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   73.0000  -51.6294 54

 25 omega   77.00  102.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -150.0000 25

 26 omega   77.00  105.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -180.0000 28

 27 omega   64.00   90.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   53.0000 -145.0224 26

 28 omega   64.00   99.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   51.0000 -114.3153 35

 29 omega   62.00  100.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   77.0000  -66.0988 38

 30 omega   57.00   82.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   67.0000  -77.7867 25

 31 omega   48.00   73.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   75.0000  -18.3398 25

 32 omega   38.00   67.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -74.2662 29

 33 omega   35.00   78.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000 -138.8403 43

 34 omega   78.00  103.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8828   57.0000 -150.0000 25

 35 omega   26.00   52.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  -86.3535 26

 36 omega   26.00   52.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000 -144.3556 26

 37 omega   11.00   37.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8828   57.0000 -150.0000 26

 38 omega    7.00   32.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000 -158.0654 25

 39 omega   13.00   38.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   83.0000  -60.4184 25

 40 omega   29.00   55.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  -20.2407 26

 41 omega   28.00   53.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000   49.0744 25

 42 omega   47.00   74.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   59.0000   40.4825 27

 43 omega   59.00   93.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   56.0000   74.0257 34

 44 omega   77.00  146.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000  120.0000 69

 45 omega   77.00  161.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000  150.0000 84

 46 omega   56.00   82.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   71.0000  165.1266 26

 47 omega   61.00   88.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   64.0000  120.4477 27

 48 omega   47.00   73.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   72.0000  136.4754 26

 49 omega   48.00   74.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   68.0000  103.7961 26

 50 omega   36.00   61.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000   69.6981 25

 51 omega   17.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  132.4355 25

 52 omega   34.00   60.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  162.2264 26

 53 omega    3.00   28.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   87.0000   18.9930 25

 54 omega   31.00  107.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  120.0000 76

 55 omega   17.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000   20.4096 25

 56 omega  -48.00   35.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828   37.0000  150.0000 83

 57 omega  -52.00  -21.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -37.0000   60.0000 31

 58 omega -120.00   -7.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -77.0000   30.0000 113

 59 omega  -50.00  -12.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -57.0000 -180.0000 38

 60 omega -115.00  -54.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -57.0000 -180.0000 61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1414236000
_diffrn_orient_matrix_UB_12      0.0158209000
_diffrn_orient_matrix_UB_13      0.0568169000
_diffrn_orient_matrix_UB_21      -0.0854212000
_diffrn_orient_matrix_UB_22      0.0434726000
_diffrn_orient_matrix_UB_23      -0.0847093000
_diffrn_orient_matrix_UB_31      -0.0297256000
_diffrn_orient_matrix_UB_32      -0.1064117000
_diffrn_orient_matrix_UB_33      -0.0206811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29333
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.36
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     979
_refine_ls_number_reflns         12497
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                11943
_reflns_number_total             12497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04977f2.cif
_cod_data_source_block           keil7a
_cod_depositor_comments
;

2024-03-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1824.74(7)
_cod_original_sg_symbol_H-M      P1
_cod_original_formula_moiety     'C72 H72 B4 Na4 O28'
_cod_original_formula_sum        'C72 H72 B4 Na4 O28'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1520.50
_cod_database_code               7117980
_reflns_odcompleteness_completeness 99.94
_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 O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O1SA(0.42) H1SA(0.21) H1SB(0.21) C1SA(0.42) H1SC(0.42) H1SD(0.42)
 C2SA(0.42) H2SA(0.42) H2SB(0.42) H2SC(0.42) O1SB(0.58) H1SE(0.29) H1SF(0.29)
 C1SB(0.58) H1SG(0.58) H1SH(0.58) C2SB(0.58) H2SD(0.58) H2SE(0.58) H2SF(0.58)
3.a Riding coordinates:
 O1SA(H1SA,H1SB), C1SA(H1SC,H1SD), O1SB(H1SE,H1SF), O11S(H11S), O31S(H31S)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C12(H12), C22(H22), C32(H32), C42(H42), C52(H52), C62(H62), C72(H72)
3.c Secondary CH2 refined with riding coordinates:
 C1SB(H1SG,H1SH), C11S(H11A,H11B), C21S(H21A,H21B), C31S(H31A,H31B)
3.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38), C44(H44), C45(H45), C46(H46),
 C47(H47), C48(H48), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58), C64(H64),
  C65(H65), C66(H66), C67(H67), C68(H68), C74(H74), C75(H75), C76(H76),
 C77(H77), C78(H78)
3.e Idealised Me refined as rotating group:
 C2SA(H2SA,H2SB,H2SC), C2SB(H2SD,H2SE,H2SF), C12S(H12A,H12B,H12C), C22S(H22A,
 H22B,H22C), C32S(H32A,H32B,H32C)
;
_olex2_submission_original_sample_id keil7a
_olex2_submission_special_instructions 'No special instructions were received'