Phosphine-catalyzed cage carbon functionalization of o-carborane: facile synthesis of alkenylcarboranes.
Zheng, Fangrui; Leung, Tsz-Fai; Chan, Ka-Wing; Sung, Herman H. Y.; Williams, Ian D.; Xie, Zuowei; Jia, Guochen; Chemical communications (Cambridge, England) 52 (2016) 10767–10770; doi:10.1039/c6cc05283e

data_7124867
_publ_section_title
;
 Phosphine-catalyzed cage carbon functionalization of o-carborane: facile
 synthesis of alkenylcarboranes.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10767
_journal_page_last               10770
_journal_paper_doi               10.1039/c6cc05283e
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C13 H21 B10 Br O2'
_chemical_formula_sum            'C13 H21 B10 Br O2'
_chemical_formula_weight         397.31
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-20 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.6871(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3765(2)
_cell_length_b                   6.99225(9)
_cell_length_c                   19.7177(3)
_cell_measurement_reflns_used    5452
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.0930
_cell_measurement_theta_min      6.3970
_cell_volume                     1908.28(5)
_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, 2008)'
_computing_structure_solution    'ShelXS (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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega   77.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000    0.0000 31

  2 omega  -33.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8828  -57.0000   60.0000 102

  3 omega   48.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -60.0000 40

  4 omega   55.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000  -90.0000 121

  5 omega  109.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000   90.0000 69

  6 omega   94.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  150.0000 75

  7 omega   47.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000   90.0000 51

  8 omega   36.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000    0.0000 52

  9 omega   37.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000    0.0000 36

 10 omega   26.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -120.0000 81

 11 omega   37.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -150.0000 61

 12 omega   32.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  120.0000 76

 13 omega  -65.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828   57.0000  -30.0000 96

 14 omega -108.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -57.0000 -180.0000 93
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1101141000
_diffrn_orient_matrix_UB_12      0.0296758000
_diffrn_orient_matrix_UB_13      0.0253588000
_diffrn_orient_matrix_UB_21      -0.0033776000
_diffrn_orient_matrix_UB_22      0.1142718000
_diffrn_orient_matrix_UB_23      -0.0674212000
_diffrn_orient_matrix_UB_31      -0.0155796000
_diffrn_orient_matrix_UB_32      0.1861550000
_diffrn_orient_matrix_UB_33      0.0373417000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10084
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.483
_diffrn_reflns_theta_min         4.659
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91397
_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    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+1.1840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3036
_reflns_number_total             3408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05283e2.cif
_cod_data_source_block           cpd3i_zheng5cult
_cod_database_code               7124867
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C12(H12A), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.d Boron cage BH refined with riding coordinates:
 B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9), B10(H10), B11(H11),
 B12(H12), C2(H2)
;
_shelx_res_checksum              82981
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-29
_olex2_submission_special_instructions 'No special instructions were received'