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_7124872
_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 O2 S'
_chemical_formula_sum            'C11 H20 B10 O2 S'
_chemical_formula_weight         324.43
_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     iterative
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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2015-10-20 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.292(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.009(2)
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_cell_length_c                   17.9756(19)
_cell_measurement_reflns_used    972
_cell_measurement_temperature    99.94(14)
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_cell_measurement_theta_min      6.3820
_cell_volume                     1736.5(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_environment      N~2~
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_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega   36.00  141.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000 -150.0000 105

  2 omega  -49.00   35.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000 -120.0000 84

  3 omega  -96.00   -2.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  125.0000  -30.0000 94

  4 omega  -49.00   35.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000   90.0000 84

  5 omega   28.00  110.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -98.0000  121.0000 82

  6 omega   94.00  178.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000 -180.0000 84

  7 omega   83.00  178.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000    0.0000 95

  8 omega -115.00  -53.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000  -60.0000 62

  9 omega -115.00  -11.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000  120.0000 104
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
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_diffrn_orient_matrix_UB_11      -0.0540654000
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_diffrn_orient_matrix_UB_13      -0.0818371000
_diffrn_orient_matrix_UB_21      -0.0547839000
_diffrn_orient_matrix_UB_22      0.1886498000
_diffrn_orient_matrix_UB_23      0.0059628000
_diffrn_orient_matrix_UB_31      0.0809632000
_diffrn_orient_matrix_UB_32      0.1102623000
_diffrn_orient_matrix_UB_33      -0.0291283000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.1455
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_k_min       -6
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_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6809
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.965
_diffrn_reflns_theta_min         4.405
_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    1.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81855
_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
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_exptl_crystal_size_mid          0.15
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_refine_diff_density_max         0.338
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_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0636
_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=exp[0.9050(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0122P)^2^] 
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                1783
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05283e2.cif
_cod_data_source_block           cpd3o_zheng10cult
_cod_database_code               7124872
_reflns_odcompleteness_completeness 98.79
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_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), C14(H14)
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              19410
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-07
_olex2_submission_special_instructions 'No special instructions were received'