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_7124869
_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         'C17 H24 B10 O2'
_chemical_formula_sum            'C17 H24 B10 O2'
_chemical_formula_weight         368.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-27
_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                109.896(4)
_cell_angle_beta                 91.522(4)
_cell_angle_gamma                105.035(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5123(3)
_cell_length_b                   11.5047(5)
_cell_length_c                   13.1285(6)
_cell_measurement_reflns_used    3754
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      75.3680
_cell_measurement_theta_min      4.2550
_cell_volume                     1022.13(9)
_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      air
_diffrn_ambient_temperature      173(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega   51.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000   30.0000 127

  2 omega   95.00  160.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -90.0000 65

  3 omega   55.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -150.0000 36

  4 omega   42.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 72

  5 omega   81.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000   90.0000 28

  6 omega   42.00  139.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000  120.0000 97

  7 omega   34.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000   90.0000 26

  8 omega   33.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 54

  9 omega   36.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   60.0000 53

 10 omega   36.00  135.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  -30.0000 99

 11 omega  -27.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453  -77.0000 -180.0000 102

 12 omega -106.00   -7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -77.0000   60.0000 99

 13 omega -114.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000  -60.0000 102
;
_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      0.1662543000
_diffrn_orient_matrix_UB_12      0.1028868000
_diffrn_orient_matrix_UB_13      0.0795075000
_diffrn_orient_matrix_UB_21      0.0917198000
_diffrn_orient_matrix_UB_22      0.0249170000
_diffrn_orient_matrix_UB_23      -0.0970568000
_diffrn_orient_matrix_UB_31      -0.0988342000
_diffrn_orient_matrix_UB_32      0.1042802000
_diffrn_orient_matrix_UB_33      0.0092163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0102
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5461
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         4.264
_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    0.502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77279
_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    1.197
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.044
_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     259
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0830P)^2^+0.4490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3290
_reflns_number_total             3605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05283e2.cif
_cod_data_source_block           cpd3k_zheng2cult
_cod_original_cell_volume        1022.14(8)
_cod_database_code               7124869
_reflns_odcompleteness_completeness 98.59
_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
 O2A-C6A = O2-C6
 1.4 with sigma of 0.02
 C3-C5A = C3-C5
 1.52 with sigma of 0.02
 C7A-C6A = C7-C6
 1.52 with sigma of 0.02
 O2-C6 \\sim O2A-C6A
 with sigma of 0.02
 O2-C5 \\sim O2A-C5A
 with sigma of 0.02
 O1A-C5A \\sim O1-C5
 with sigma of 0.02
 C7A-C6A \\sim C7-C6
 with sigma of 0.02
3. Others
 Fixed Sof: O1(0.7) O1A(0.3) O2(0.82) O2A(0.18) C5(0.65) C5A(0.35) C6(0.82)
 H6A(0.82) H6B(0.82) C6A(0.18) H6AA(0.18) H6AB(0.18) C7(0.88) H7A(0.88)
 H7B(0.88) H7C(0.88) C7A(0.12) H7AA(0.12) H7AB(0.12) H7AC(0.12)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C12(H12A), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC)
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)
;
_shelx_res_checksum              97354
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-30
_olex2_submission_special_instructions 'No special instructions were received'