Synthesis, structures and catalytic activity of some BINOL based boronates and boronium salts.
Garg, Shipra; Unruh, Daniel K.; Krempner, Clemens; Dalton transactions (Cambridge, England : 2003) 50 (2021) 5044–5049; doi:10.1039/d1dt00842k

data_7706954
_publ_section_title
;
 Synthesis, structures and catalytic activity of some BINOL based
 boronates and boronium salts.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5044
_journal_page_last               5049
_journal_paper_doi               10.1039/d1dt00842k
_journal_volume                  50
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H24 B O4, C16 H34 N4 P, 2(C H2 Cl2)'
_chemical_formula_sum            'C58 H62 B Cl4 N4 O4 P'
_chemical_formula_weight         1062.69
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-02-01 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.93710(10)
_cell_length_b                   19.13750(10)
_cell_length_c                   12.85790(10)
_cell_measurement_reflns_used    54483
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.3430
_cell_measurement_theta_min      3.4310
_cell_volume                     2689.32(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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     26.00 121.00   0.50    0.05    --   48.15  77.00 -30.00  190
  2  \w     26.00 121.00   0.50    0.05    --   48.15  77.00 -90.00  190
  3  \w     33.00 121.00   0.50    0.05    --   48.15  57.00-120.00  176
  4  \w     26.00  95.00   0.50    0.05    --   48.15  77.00  60.00  138
  5  \w     33.00 121.00   0.50    0.05    --   48.15  57.00  60.00  176
  6  \w     26.00 121.00   0.50    0.05    --   48.15  77.00 120.00  190
  7  \w     26.00 121.00   0.50    0.05    --   48.15  77.00 150.00  190
  8  \w     88.00 178.00   0.50    0.15    --  107.75 136.00  44.00  180
  9  \w     95.00 178.00   0.50    0.15    --  107.75 125.00 120.00  166
 10  \w     95.00 178.00   0.50    0.15    --  107.75 125.00 150.00  166
 11  \w     95.00 178.00   0.50    0.15    --  107.75 125.00  90.00  166
 12  \w     90.00 178.00   0.50    0.15    --  107.75 133.00-134.00  176
 13  \w     95.00 178.00   0.50    0.15    --  107.75 125.00-180.00  166
 14  \w     95.00 178.00   0.50    0.15    --  107.75  30.00  30.00  166
 15  \w     94.00 178.00   0.50    0.15    --  107.75  15.00 -30.00  168
 16  \w     94.00 178.00   0.50    0.15    --  107.75  15.00 120.00  168
 17  \w     35.00  73.00   0.50    0.15    --  107.75 -61.00 150.00   76
 18  \w     35.00 107.00   0.50    0.15    --  107.75 -77.00 150.00  144
 19  \w     35.00 107.00   0.50    0.15    --  107.75 -77.00 120.00  144
 20  \w     35.00  73.00   0.50    0.15    --  107.75 -61.00  60.00   76
 21  \w    -26.00  28.00   0.50    0.05    --   48.15 -19.00-180.00  108
 22  \w     35.00  73.00   0.50    0.15    --  107.75 -61.00-150.00   76
 23  \w     35.00 106.00   0.50    0.15    --  107.75 -94.00-150.00  142
 24  \w     35.00 112.00   0.50    0.15    --  107.75-125.00-180.00  154
 25  \w     41.00 102.00   0.50    0.05    --   48.15-136.00 -20.00  122
 26  \w     35.00 112.00   0.50    0.15    --  107.75-125.00 -90.00  154
 27  \w     35.00 107.00   0.50    0.15    --  107.75-102.00 -45.52  144
 28  \w     35.00 106.00   0.50    0.15    --  107.75 -94.00-180.00  142
 29  \w     41.00 120.00   0.50    0.15    --  107.75-136.00 -20.00  158
 30  \w     35.00 106.00   0.50    0.15    --  107.75 -94.00 -30.00  142
 31  \w     35.00 106.00   0.50    0.15    --  107.75 -94.00   0.00  142
 32  \w     35.00 106.00   0.50    0.15    --  107.75 -94.00  60.00  142
 33  \w     39.00 100.00   0.50    0.05    --   48.15-133.00 158.00  122
 34  \w     39.00 118.00   0.50    0.15    --  107.75-133.00 158.00  158
 35  \w    -94.00 -19.00   0.50    0.05    --  -48.15 136.00  44.00  150
 36  \w    -86.00 -13.00   0.50    0.15    --  -86.25 125.00 120.00  146
 37  \w    -94.00 -19.00   0.50    0.15    --  -86.25 136.00  44.00  150
 38  \w    -92.00 -17.00   0.50    0.15    --  -86.25 133.00-134.00  150
 39  \w    -92.00 -17.00   0.50    0.05    --  -48.15 133.00-134.00  150
 40  \w    -49.00 -14.00   0.50    0.15    --  -86.25  45.00   0.00   70
 41  \w    -49.00 -14.00   0.50    0.15    --  -86.25  45.00  30.00   70
 42  \w    -49.00 -14.00   0.50    0.15    --  -86.25  45.00  90.00   70
 43  \w    -69.00 -13.00   0.50    0.15    --  -86.25  61.00 120.00  112
 44  \w    -49.00 -14.00   0.50    0.15    --  -86.25  45.00  60.00   70
 45  \w    -49.00 -14.00   0.50    0.15    --  -86.25  45.00 -90.00   70
 46  \w    -49.00 -14.00   0.50    0.15    --  -86.25  45.00-120.00   70
 47  \w    -24.00  27.00   0.50    0.05    --  -48.15  19.00-120.00  102
 48  \w    -24.00  27.00   0.50    0.05    --  -48.15  19.00 -90.00  102
 49  \w    -24.00  27.00   0.50    0.05    --  -48.15  19.00 -30.00  102
 50  \w    -24.00  27.00   0.50    0.05    --  -48.15  19.00  30.00  102
 51  \w    -24.00  27.00   0.50    0.05    --  -48.15  19.00  90.00  102
 52  \w    -24.00  27.00   0.50    0.05    --  -48.15  19.00 150.00  102
 53  \w   -121.00 -66.00   0.50    0.05    --  -48.15-136.00 -20.00  110
 54  \w   -159.00 -66.00   0.50    0.15    --  -86.25-136.00 -20.00  186
 55  \w   -121.00 -68.00   0.50    0.05    --  -48.15-133.00 158.00  106
 56  \w   -159.00 -68.00   0.50    0.15    --  -86.25-133.00 158.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0202987000
_diffrn_orient_matrix_UB_12      0.0784846000
_diffrn_orient_matrix_UB_13      -0.0210457000
_diffrn_orient_matrix_UB_21      0.0857223000
_diffrn_orient_matrix_UB_22      0.0179487000
_diffrn_orient_matrix_UB_23      0.0940488000
_diffrn_orient_matrix_UB_31      0.1100054000
_diffrn_orient_matrix_UB_32      0.0005394000
_diffrn_orient_matrix_UB_33      -0.0713377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            65152
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.735
_diffrn_reflns_theta_min         3.440
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.681
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_recrystallization_method
'Slow evaporation from dichloromethane'
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 5073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         11148
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+1.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                10949
_reflns_number_total             11148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt00842k2.cif
_cod_data_source_block           R-8_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7706949--7706955.cif.'
_cod_database_code               7706954
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C118  H130  B2  N10  O12  P6  '
_shelx_estimated_absorpt_t_max   0.554
_shelx_estimated_absorpt_t_min   0.504
_reflns_odcompleteness_completeness 99.92
_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
 Cl1A-C56A = Cl2A-C56A = Cl1B-C56B = Cl2B-C56B
 1.76328 with sigma of 0.02
 Cl3A-C57A = Cl4A-C57A = Cl3B-C57B = Cl4B-C57B
 1.76328 with sigma of 0.02
 Cl3C-C57C = Cl4C-C57C
 1.76328 with sigma of 0.02
 Cl1A-Cl2A = Cl1B-Cl2B = Cl3A-Cl4A = Cl3B-Cl4B = Cl3C-Cl4C
 2.93183 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl3A \\sim Cl4A \\sim C57A \\sim Cl3B \\sim Cl4B \\sim C57B \\sim Cl3C \\sim
Cl4C \\sim C57C: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
Cl1A \\sim Cl2A \\sim Cl1B \\sim Cl2B \\sim C56A \\sim C56B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 1*[Sof(Cl3A)+Sof(Cl4A)+Sof(C57A)+Sof(H57A)+Sof(H57B)]+1*[Sof(Cl3B)+Sof(Cl4B)+
 Sof(C57B)+Sof(H57C)+Sof(H57D)]+1*[Sof(Cl3C)+Sof(Cl4C)+Sof(C57C)+Sof(H57E)+
 Sof(H57F)]=1 with esd of 0
 Sof(Cl1B)=Sof(Cl2B)=Sof(C56B)=Sof(H56C)=Sof(H56D)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C56A)=Sof(H56A)=Sof(H56B)=FVAR(1)
 1(DFIX)=1(DFIX)=1(DFIX)=FVAR(2)
 Sof(Cl3A)=Sof(Cl4A)=Sof(C57A)=Sof(H57A)=Sof(H57B)=FVAR(3)
 Sof(Cl3B)=Sof(Cl4B)=Sof(C57B)=Sof(H57C)=Sof(H57D)=FVAR(4)
 Sof(Cl3C)=Sof(Cl4C)=Sof(C57C)=Sof(H57E)=Sof(H57F)=FVAR(5)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C56A(H56A,H56B), C56B(H56C,H56D), C57A(H57A,
 H57B), C57B(H57C,H57D), C57C(H57E,H57F)
5.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
 C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C39(H39), C40(H40), C41(H41),
  C42(H42), C44(H44), C45(H45), C48(H48), C49(H49), C51(H51), C52(H52),
 C53(H53), C54(H54)
5.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              11925
_shelx_hkl_checksum              62225
_olex2_date_sample_data_collection 2020-09-15
_olex2_date_sample_submission    2020-09-15
_olex2_exptl_crystal_mounting_method 'MiTeGen 100 um MicroLoop'
_olex2_submission_original_sample_id kre20_31
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   6723
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.776