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_7124864
_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         'C14 H24 B10 O2'
_chemical_formula_sum            'C14 H24 B10 O2'
_chemical_formula_weight         332.43
_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
_atom_sites_solution_secondary   difmap
_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                70.985(10)
_cell_angle_beta                 82.699(7)
_cell_angle_gamma                79.375(7)
_cell_formula_units_Z            2
_cell_length_a                   6.9249(5)
_cell_length_b                   11.0485(12)
_cell_length_c                   13.4241(14)
_cell_measurement_reflns_used    1163
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.7280
_cell_measurement_theta_min      4.6040
_cell_volume                     951.90(17)
_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      173.00(10)
_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 0.981
_diffrn_measurement_details
;
  1 omega   44.00  120.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000    0.0000 76

  2 omega  -33.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  -60.0000 68

  3 omega  -66.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   77.0000  150.0000 104

  4 omega  -66.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   57.0000   60.0000 98

  5 omega   29.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  -60.0000 56

  6 omega   54.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 34

  7 omega   87.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000   60.0000 89

  8 omega   85.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -30.0000 92

  9 omega   42.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000   60.0000 56

 10 omega   37.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   60.0000 71

 11 omega   37.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -60.0000 48

 12 omega   41.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -150.0000 45

 13 omega   27.00  107.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -150.0000 80

 14 omega   33.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 52
;
_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      0.0775074000
_diffrn_orient_matrix_UB_12      0.1294562000
_diffrn_orient_matrix_UB_13      -0.0245672000
_diffrn_orient_matrix_UB_21      0.0438078000
_diffrn_orient_matrix_UB_22      0.0057446000
_diffrn_orient_matrix_UB_23      -0.1167383000
_diffrn_orient_matrix_UB_31      -0.2087463000
_diffrn_orient_matrix_UB_32      0.0740072000
_diffrn_orient_matrix_UB_33      -0.0240803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.1094
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5179
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         4.28
_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    0.483
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86006
_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    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.186
_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     237
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 calc 
 [0.00000+1.00000exp(1.50(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0120P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                2107
_reflns_number_total             3357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc05283e2.cif
_cod_data_source_block           cpd3b_zheng3cult
_cod_original_cell_volume        951.90(16)
_cod_database_code               7124864
_chemical_oxdiff_formula         'B2 Ph3 O2'
_reflns_odcompleteness_completeness 98.34
_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), C17(H17A,H17B,H17C)
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)
;
_olex2_date_sample_data_collection 2015-05-20
_olex2_submission_special_instructions 'No special instructions were received'