9-Borabicyclo[3.3.1]nonane: a metal-free catalyst for the hydroboration of carbodiimides
Ramos, Alberto; Antiñolo, Antonio; Carrillo-Hermosilla, Fernando; Fernández-Galán, Rafael; García-Vivó, Daniel; Chemical Communications  (2019) –; doi:10.1039/C9CC00593E

data_7123017
_publ_section_title
;
 9-Borabicyclo[3.3.1]nonane: a metal-free catalyst for the hydroboration
 of carbodiimides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00593E
_journal_year                    2019
_chemical_formula_sum            'C15 H31 B N2 O2'
_chemical_formula_weight         282.23
_chemical_name_common            1c
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016
_audit_update_record
;
2018-11-29 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.070(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.05230(10)
_cell_length_b                   15.6534(4)
_cell_length_c                   18.9600(4)
_cell_measurement_reflns_used    4394
_cell_measurement_temperature    154.9(7)
_cell_measurement_theta_max      69.3820
_cell_measurement_theta_min      3.6720
_cell_volume                     1782.60(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SUPERFLIP
_diffrn_ambient_temperature      154.9(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2640
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9950
_diffrn_measured_fraction_theta_max 0.9882
_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   -109.00 -82.60   1.10    2.50    --  -43.23 -99.00   0.00   24
  2  \w   -122.00 -95.60   1.10    2.50    --  -43.23 -99.00  90.00   24
  3  \w     20.00 110.20   1.10    2.50    --   43.23  57.00 150.00   82
  4  \w     49.00  93.00   1.10    2.50    --   43.23-125.00  60.00   40
  5  \w     97.00 150.90   1.10    7.50    --   94.50  61.00 -30.00   49
  6  \w    106.00 166.50   1.10    7.50    --   94.50  30.00  60.00   55
  7  \w     22.00 119.90   1.10    7.50    --   94.50 -30.00 150.00   89
  8  \w     88.00 116.60   1.10    7.50    --   94.50 125.00  60.00   26
  9  \w     25.00  74.50   1.10    7.50    --   94.50 -94.00-180.00   45
 10  \w     31.00 110.20   1.10    7.50    --   94.50 -61.00-180.00   72
 11  \w     24.00 114.20   1.10    7.50    --   94.50-124.00 149.00   82
 12  \w     71.00 109.50   1.10    7.50    --   94.50 -94.00 150.00   35
 13  \w     80.00 104.20   1.10    7.50    --   94.50-125.00 -60.00   22
 14  \w     16.00  65.50   1.10    7.50    --   94.50 -94.00 150.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0214345000
_diffrn_orient_matrix_UB_12      0.0967032000
_diffrn_orient_matrix_UB_13      -0.0141947000
_diffrn_orient_matrix_UB_21      -0.0043074000
_diffrn_orient_matrix_UB_22      0.0160458000
_diffrn_orient_matrix_UB_23      0.0799967000
_diffrn_orient_matrix_UB_31      0.2556081000
_diffrn_orient_matrix_UB_32      0.0083111000
_diffrn_orient_matrix_UB_33      0.0102993000
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9243
_diffrn_reflns_theta_full        68.1328
_diffrn_reflns_theta_max         69.3913
_diffrn_reflns_theta_min         3.6731
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0913P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2737
_reflns_number_total             3301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00593e2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1782.59(7)
_cod_database_code               7123017
_cell_oxdiff_length_a            6.0514(3)
_cell_oxdiff_length_b            15.6598(9)
_cell_oxdiff_length_c            18.9559(7)
_cell_oxdiff_angle_alpha         89.980(4)
_cell_oxdiff_angle_beta          97.087(4)
_cell_oxdiff_angle_gamma         89.963(5)
_cell_oxdiff_volume              1782.59(16)
_cell_oxdiff_measurement_reflns_used 4394
_oxdiff_exptl_absorpt_empirical_full_min 0.301
_oxdiff_exptl_absorpt_empirical_full_max 4.307
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              51221