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_7124871
_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         'C11 H20 B10 O3'
_chemical_formula_sum            'C11 H20 B10 O3'
_chemical_formula_weight         308.37
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-07
_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                90.00
_cell_angle_beta                 100.0500(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.1533(3)
_cell_length_b                   6.78019(7)
_cell_length_c                   23.3341(3)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    99.96(10)
_cell_measurement_theta_max      75.2480
_cell_measurement_theta_min      5.0710
_cell_volume                     3451.09(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  -71.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   77.0000  -30.0000 109

  2 omega  -69.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   77.0000 -150.0000 107

  3 omega   23.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8203 -125.0000   60.0000 69

  4 omega   96.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000  -30.0000 26

  5 omega   53.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000    0.0000 91

  6 omega   54.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000  120.0000 114

  7 omega  121.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000    0.0000 57

  8 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000  150.0000 97

  9 omega   37.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000  -30.0000 27

 10 omega   37.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000 -120.0000 84

 11 omega   33.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -90.0000 33

 12 omega   32.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000 -120.0000 98

 13 omega -115.00  -29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000   90.0000 86
;
_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      -0.0537013000
_diffrn_orient_matrix_UB_12      0.0567672000
_diffrn_orient_matrix_UB_13      -0.0484944000
_diffrn_orient_matrix_UB_21      -0.0443687000
_diffrn_orient_matrix_UB_22      -0.1180493000
_diffrn_orient_matrix_UB_23      0.0309518000
_diffrn_orient_matrix_UB_31      -0.0117821000
_diffrn_orient_matrix_UB_32      0.1853346000
_diffrn_orient_matrix_UB_33      0.0345309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19628
_diffrn_reflns_theta_full        75.46
_diffrn_reflns_theta_max         75.46
_diffrn_reflns_theta_min         5.08
_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    0.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89017
_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    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6963
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+1.4010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                6104
_reflns_number_total             6963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc05283e2.cif
_cod_data_source_block           cpd3m_zheng8cult
_cod_database_code               7124871
_chemical_oxdiff_formula         'B10 C11 H15 O1'
_reflns_odcompleteness_completeness 99.68
_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. Restrained distances
 C7A-C6A
 1.52 with sigma of 0.01
 C7A-C6A \\sim C7B-C6B
 with sigma of 0.02
 O2A-C6A \\sim O2A-C6B
 with sigma of 0.02
3. Others
 Fixed Sof: C6A(0.45) H6AA(0.45) H6AB(0.45) C6B(0.55) H6BA(0.55) H6BB(0.55)
 C7A(0.45) H7AA(0.45) H7AB(0.45) H7AC(0.45) C7B(0.55) H7BA(0.55) H7BB(0.55)
 H7BC(0.55)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6B,H6C), C6A(H6AA,H6AB), C6B(H6BA,H6BB)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4B), C12(H12C), C13(H13), C14(H14), C5A(H5AA), C12A(H12B), C13A(H13A),
 C14A(H14A)
4.c Idealised Me refined as rotating group:
 C7(H7B,H7C,H7D), C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC)
4.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), B3A(H3A), B4A(H4A), B5A(H5A), B6A(H6A), B7A(H7A), B8A(H8A),
 B9A(H9A), B10A(H10A), B11A(H11A), B12A(H12A), C2A(H2A)
;
_olex2_date_sample_data_collection 2015-07-15
_olex2_submission_special_instructions 'No special instructions were received'