Catalytic Hydroboration of Aldehydes, Ketones, Alkynes and Alkenes Initiated by NaOH
Wu, Yile; Shan, Changkai; Ying, Jianxi; Su, Jue; Zhu, Jun; Liu, Liu Leo; Zhao, Yufen; Green Chem.  (2017) –; doi:10.1039/C7GC01632H

data_7228815
_publ_section_title
;
 Catalytic Hydroboration of Aldehydes, Ketones, Alkynes and Alkenes
 Initiated by NaOH
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC01632H
_journal_year                    2017
_chemical_formula_moiety         'C18 H36 B Na O5'
_chemical_formula_sum            'C18 H36 B Na O5'
_chemical_formula_weight         366.27
_chemical_name_systematic
;
 ?
;
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-08 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                93.500(6)
_cell_angle_beta                 90.410(5)
_cell_angle_gamma                104.176(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5751(5)
_cell_length_b                   10.0045(7)
_cell_length_c                   13.9038(9)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      65.8500
_cell_measurement_theta_min      4.5640
_cell_volume                     1019.44(12)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9690
_diffrn_measurement_details
;
  1 omega  -17.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.3583   37.0000  -30.0000 85

  2 omega    5.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.3583   37.0000   60.0000 47

  3 omega   42.00  119.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632  -77.0000   30.0000 77

  4 omega   83.00  162.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632   30.0000  -90.0000 79

  5 omega   94.00  141.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632  125.0000 -180.0000 47

  6 omega   96.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632  125.0000  -60.0000 25

  7 omega   60.00  152.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632   77.0000    0.0000 92

  8 omega   75.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632   77.0000  120.0000 84

  9 omega   35.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632  -30.0000   30.0000 25

 10 omega   23.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632  -61.0000  150.0000 85

 11 omega   28.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632 -125.0000    0.0000 89

 12 omega   50.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632  -45.0000 -150.0000 27

 13 omega   80.00  119.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       89.0632 -125.0000 -150.0000 39

 14 omega  -72.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        1.3583 -178.0000 -150.0000 35

 15 omega  -81.00  -36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -1.3583 -178.0000   60.0000 45
;
_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      -0.1601468000
_diffrn_orient_matrix_UB_12      -0.0639805000
_diffrn_orient_matrix_UB_13      0.0638245000
_diffrn_orient_matrix_UB_21      -0.0376700000
_diffrn_orient_matrix_UB_22      0.1434223000
_diffrn_orient_matrix_UB_23      0.0205067000
_diffrn_orient_matrix_UB_31      -0.1302136000
_diffrn_orient_matrix_UB_32      -0.0258396000
_diffrn_orient_matrix_UB_33      -0.0885170000
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5838
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.973
_diffrn_reflns_theta_min         4.568
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80144
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0680P)^2^+0.3400P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3193
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc01632h2.cif
_cod_data_source_block           exp_1914
_cod_original_cell_volume        1019.45(12)
_cod_database_code               7228815
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H0AA,H1B), C14(H14A,H14B), C18(H18A,H18B), C3(H3A,H3B), C16(H16A,H16B),
 C4(H4A,H4B), C2(H1AA,H2B), C5(H5A,H5B), C8(H8A,H8B), C17(H17A,H17B), C9(H9A,
 H9B), C12(H12A,H12B), C10(H10A,H10B), C13(H13A,H13B)
;
_olex2_submission_special_instructions 'No special instructions were received'