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_7124866
_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 Cl O2'
_chemical_formula_sum            'C13 H21 B10 Cl O2'
_chemical_formula_weight         352.85
_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
_audit_creation_date             2015-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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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                 103.257(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2465(15)
_cell_length_b                   6.9536(7)
_cell_length_c                   19.296(3)
_cell_measurement_reflns_used    1111
_cell_measurement_temperature    99.95(13)
_cell_measurement_theta_max      27.7610
_cell_measurement_theta_min      3.6340
_cell_volume                     1860.6(4)
_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
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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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
  1 omega  -20.00   60.00   0.5000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -99.0000  -30.0000 160

  2 omega  -16.00   95.00   0.5000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   37.0000   90.0000 222

  3 omega  -62.00  -37.00   0.5000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000   90.0000 50
;
_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      0.0032599000
_diffrn_orient_matrix_UB_12      0.0038713000
_diffrn_orient_matrix_UB_13      -0.0361393000
_diffrn_orient_matrix_UB_21      0.0458076000
_diffrn_orient_matrix_UB_22      -0.0450406000
_diffrn_orient_matrix_UB_23      0.0091833000
_diffrn_orient_matrix_UB_31      -0.0224375000
_diffrn_orient_matrix_UB_32      -0.0914333000
_diffrn_orient_matrix_UB_33      -0.0060648000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1525
_diffrn_reflns_av_unetI/netI     0.2693
_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            7288
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         3.557
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02658
_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    1.260
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.065
_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         3326
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1786
_refine_ls_R_factor_gt           0.0795
_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[2.0220(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0130P)^2^] 
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1383
_reflns_number_total             3326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05283e2.cif
_cod_data_source_block           cpd3h_zheng9molt
_cod_database_code               7124866
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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
 C7-C6
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(B10) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C12(H12A), C13(H13), C15(H15), C16(H16)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
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              62760
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-29
_olex2_submission_special_instructions 'No special instructions were received'