#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:24:20 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135283.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4135283
loop_
_publ_author_name
'Ni, Hangcheng'
'Lu, Zhenpin'
'Xie, Zuowei'
_publ_section_title
;
 Transition-Metal-Free Cross-Coupling Reaction of Iodocarboranes with
 Terminal Alkynes Enabled by UV Light: Synthesis of
 1-Alkynyl-o-Carboranes and Carborane-Fused Cyclics.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18661
_journal_page_last               18667
_journal_paper_doi               10.1021/jacs.0c08652
_journal_volume                  142
_journal_year                    2020
_chemical_formula_sum            'C17 H28 B10'
_chemical_formula_weight         340.49
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                95.658(2)
_cell_angle_beta                 91.485(2)
_cell_angle_gamma                94.652(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8180(7)
_cell_length_b                   10.0517(9)
_cell_length_c                   13.0676(11)
_cell_measurement_reflns_used    153
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1017.94(15)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24368
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         2.043
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0809
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1627P)²+0.4138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2417
_refine_ls_wR_factor_ref         0.2847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2322
_reflns_number_total             3681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            5Bj.cif
_cod_data_source_block           5Bj
_cod_depositor_comments
'Adding full bibliography for 4135283--4135293.cif.'
_cod_database_code               4135283
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B3 B 0.2494(4) 0.4549(3) 0.8078(2) 0.0569(9) Uani 1 1 d . . . . .
B4 B 0.4328(5) 0.5649(3) 0.8146(3) 0.0770(12) Uani 0.5 1 d . . P . .
C2' C 0.4328(5) 0.5649(3) 0.8146(3) 0.0770(12) Uani 0.5 1 d . . P . .
B5 B 0.4776(7) 0.6218(5) 0.6971(4) 0.0980(18) Uani 1 1 d . . . . .
H5 H 0.5914 0.6481 0.6531 0.118 Uiso 1 1 calc R U . . .
B6 B 0.3087(8) 0.5549(5) 0.6122(3) 0.0995(18) Uani 1 1 d . . . . .
H6 H 0.3501 0.5538 0.5324 0.119 Uiso 1 1 calc R U . . .
B7 B 0.0815(5) 0.5546(4) 0.7798(3) 0.0747(12) Uani 1 1 d . . . . .
H7 H -0.0404 0.5546 0.8200 0.090 Uiso 1 1 calc R U . . .
B8 B 0.2514(5) 0.6228(4) 0.8658(3) 0.0688(11) Uani 1 1 d . . . . .
H8 H 0.2021 0.6516 0.9423 0.083 Uiso 1 1 calc R U . . .
B9 B 0.3936(6) 0.7263(4) 0.7973(4) 0.0883(14) Uani 1 1 d . . . . .
H9 H 0.4459 0.8288 0.8249 0.106 Uiso 1 1 calc R U . . .
B10 B 0.3129(7) 0.7208(5) 0.6692(4) 0.1002(18) Uani 1 1 d . . . . .
H10 H 0.3347 0.8070 0.6241 0.120 Uiso 1 1 calc R U . . .
B11 B 0.1208(7) 0.6175(5) 0.6587(3) 0.0972(17) Uani 1 1 d . . . . .
H11 H 0.0266 0.6633 0.6122 0.117 Uiso 1 1 calc R U . . .
B12 B 0.1699(6) 0.7217(4) 0.7734(3) 0.0874(15) Uani 1 1 d . . . . .
H12 H 0.0967 0.8083 0.7961 0.105 Uiso 1 1 calc R U . . .
C1 C 0.3814(5) 0.4642(3) 0.7067(2) 0.0753(11) Uani 1 1 d . . . . .
C2 C 0.1709(7) 0.4579(5) 0.6814(3) 0.0952(16) Uani 0.5 1 d . . P . .
B4' B 0.1709(7) 0.4579(5) 0.6814(3) 0.0952(16) Uani 0.5 1 d . . P . .
C11' C 0.5718(6) 0.5320(6) 0.8710(4) 0.0498(13) Uani 0.5 1 d . . P . .
C11 C 0.1167(11) 0.3472(8) 0.6324(6) 0.091(2) Uani 0.5 1 d . . P . .
C12 C 0.2500(3) 0.3239(3) 0.85881(19) 0.0453(7) Uani 1 1 d . . . . .
C13 C 0.1425(4) 0.3034(3) 0.9406(2) 0.0555(8) Uani 1 1 d . . . . .
H13A H 0.0699 0.3689 0.9619 0.067 Uiso 1 1 calc R U . . .
C14 C 0.1411(4) 0.1899(3) 0.9903(2) 0.0675(9) Uani 1 1 d . . . . .
H14A H 0.0695 0.1790 1.0451 0.081 Uiso 1 1 calc R U . . .
C15 C 0.2457(4) 0.0926(3) 0.9587(2) 0.0683(9) Uani 1 1 d . . . . .
H15A H 0.2453 0.0152 0.9922 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3522(4) 0.1085(3) 0.8772(2) 0.0591(8) Uani 1 1 d . . . . .
H16A H 0.4218 0.0408 0.8563 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3576(3) 0.2237(3) 0.82565(19) 0.0458(7) Uani 1 1 d . . . . .
C18 C 0.4717(4) 0.2391(3) 0.7377(2) 0.0514(7) Uani 1 1 d . . . . .
C19 C 0.4781(4) 0.3451(3) 0.6846(2) 0.0669(9) Uani 1 1 d . . . . .
H19A H 0.5494 0.3443 0.6287 0.080 Uiso 1 1 calc R U . . .
C20 C 0.5895(4) 0.1285(3) 0.7101(2) 0.0557(8) Uani 1 1 d . . . . .
H20A H 0.5236 0.0431 0.7176 0.067 Uiso 1 1 calc R U . . .
C21 C 0.7428(4) 0.1385(3) 0.7838(2) 0.0672(9) Uani 1 1 d . . . . .
H21A H 0.7037 0.1422 0.8538 0.081 Uiso 1 1 calc R U . . .
H21B H 0.8134 0.2208 0.7768 0.081 Uiso 1 1 calc R U . . .
C22 C 0.8507(5) 0.0192(4) 0.7636(3) 0.0839(11) Uani 1 1 d . . . . .
H22A H 0.9516 0.0316 0.8093 0.101 Uiso 1 1 calc R U . . .
H22B H 0.7843 -0.0622 0.7781 0.101 Uiso 1 1 calc R U . . .
C23 C 0.9061(5) 0.0043(4) 0.6523(3) 0.0960(13) Uani 1 1 d . . . . .
H23A H 0.9864 0.0796 0.6408 0.115 Uiso 1 1 calc R U . . .
H23B H 0.9644 -0.0771 0.6398 0.115 Uiso 1 1 calc R U . . .
C24 C 0.7552(6) -0.0015(4) 0.5787(3) 0.0916(13) Uani 1 1 d . . . . .
H24A H 0.6815 -0.0825 0.5847 0.110 Uiso 1 1 calc R U . . .
H24B H 0.7950 -0.0049 0.5088 0.110 Uiso 1 1 calc R U . . .
C25 C 0.6528(5) 0.1204(4) 0.6001(2) 0.0784(11) Uani 1 1 d . . . . .
H25A H 0.5554 0.1139 0.5519 0.094 Uiso 1 1 calc R U . . .
H25B H 0.7246 0.2013 0.5906 0.094 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 B3 C1 114.5(2) . . ?
C12 B3 B4 119.8(3) . . ?
C1 B3 B4 58.3(2) . . ?
C12 B3 C2 121.8(3) . . ?
C1 B3 C2 57.7(2) . . ?
B4 B3 C2 103.4(3) . . ?
C12 B3 B7 131.6(3) . . ?
C1 B3 B7 104.5(2) . . ?
B4 B3 B7 104.3(3) . . ?
C2 B3 B7 59.0(2) . . ?
C12 B3 B8 129.3(3) . . ?
C1 B3 B8 104.8(2) . . ?
B4 B3 B8 58.0(2) . . ?
C2 B3 B8 105.7(3) . . ?
B7 B3 B8 59.7(2) . . ?
C11' B4 C1 115.4(3) . . ?
C11' B4 B8 124.9(4) . . ?
C1 B4 B8 109.6(3) . . ?
C11' B4 B9 123.5(4) . . ?
C1 B4 B9 110.1(3) . . ?
B8 B4 B9 62.8(2) . . ?
C11' B4 B5 115.8(4) . . ?
C1 B4 B5 60.6(3) . . ?
B8 B4 B5 113.1(3) . . ?
B9 B4 B5 62.1(2) . . ?
C11' B4 B3 117.2(3) . . ?
C1 B4 B3 59.9(2) . . ?
B8 B4 B3 62.4(2) . . ?
B9 B4 B3 113.7(3) . . ?
B5 B4 B3 111.9(3) . . ?
C1 B5 B4 58.2(2) . . ?
C1 B5 B10 106.1(4) . . ?
B4 B5 B10 106.0(3) . . ?
C1 B5 B6 59.4(3) . . ?
B4 B5 B6 106.4(3) . . ?
B10 B5 B6 60.4(3) . . ?
C1 B5 B9 105.4(3) . . ?
B4 B5 B9 58.5(2) . . ?
B10 B5 B9 60.4(3) . . ?
B6 B5 B9 108.6(3) . . ?
C1 B6 C2 57.8(2) . . ?
C1 B6 B11 105.1(3) . . ?
C2 B6 B11 59.9(3) . . ?
C1 B6 B5 59.3(3) . . ?
C2 B6 B5 106.7(3) . . ?
B11 B6 B5 107.6(3) . . ?
C1 B6 B10 105.5(4) . . ?
C2 B6 B10 107.2(3) . . ?
B11 B6 B10 60.0(3) . . ?
B5 B6 B10 59.6(3) . . ?
C2 B7 B3 60.0(2) . . ?
C2 B7 B8 107.1(3) . . ?
B3 B7 B8 60.5(2) . . ?
C2 B7 B12 106.1(3) . . ?
B3 B7 B12 108.7(3) . . ?
B8 B7 B12 60.2(2) . . ?
C2 B7 B11 59.0(2) . . ?
B3 B7 B11 108.1(3) . . ?
B8 B7 B11 107.3(3) . . ?
B12 B7 B11 59.1(3) . . ?
B4 B8 B7 105.5(3) . . ?
B4 B8 B12 105.1(3) . . ?
B7 B8 B12 60.1(3) . . ?
B4 B8 B9 58.8(2) . . ?
B7 B8 B9 107.7(3) . . ?
B12 B8 B9 59.5(3) . . ?
B4 B8 B3 59.6(2) . . ?
B7 B8 B3 59.7(2) . . ?
B12 B8 B3 108.0(3) . . ?
B9 B8 B3 108.2(3) . . ?
B4 B9 B12 105.3(3) . . ?
B4 B9 B10 105.6(3) . . ?
B12 B9 B10 60.6(3) . . ?
B4 B9 B5 59.4(2) . . ?
B12 B9 B5 107.3(4) . . ?
B10 B9 B5 59.0(3) . . ?
B4 B9 B8 58.4(2) . . ?
B12 B9 B8 60.1(2) . . ?
B10 B9 B8 108.5(4) . . ?
B5 B9 B8 107.4(3) . . ?
B5 B10 B11 107.6(3) . . ?
B5 B10 B6 60.0(3) . . ?
B11 B10 B6 59.7(3) . . ?
B5 B10 B9 60.6(3) . . ?
B11 B10 B9 107.6(3) . . ?
B6 B10 B9 108.5(3) . . ?
B5 B10 B12 107.8(3) . . ?
B11 B10 B12 59.6(3) . . ?
B6 B10 B12 107.5(3) . . ?
B9 B10 B12 59.6(3) . . ?
C2 B11 B6 59.6(2) . . ?
C2 B11 B10 107.2(3) . . ?
B6 B11 B10 60.3(3) . . ?
C2 B11 B12 106.8(3) . . ?
B6 B11 B12 109.1(4) . . ?
B10 B11 B12 61.1(3) . . ?
C2 B11 B7 58.9(2) . . ?
B6 B11 B7 107.9(3) . . ?
B10 B11 B7 108.9(3) . . ?
B12 B11 B7 60.1(2) . . ?
B11 B12 B9 107.4(3) . . ?
B11 B12 B7 60.8(3) . . ?
B9 B12 B7 107.9(3) . . ?
B11 B12 B8 108.2(3) . . ?
B9 B12 B8 60.3(2) . . ?
B7 B12 B8 59.7(2) . . ?
B11 B12 B10 59.2(3) . . ?
B9 B12 B10 59.7(3) . . ?
B7 B12 B10 107.9(3) . . ?
B8 B12 B10 107.9(3) . . ?
C19 C1 C2 121.3(3) . . ?
C19 C1 B4 118.3(3) . . ?
C2 C1 B4 109.9(3) . . ?
C19 C1 B3 114.1(2) . . ?
C2 C1 B3 62.6(2) . . ?
B4 C1 B3 61.8(2) . . ?
C19 C1 B5 120.3(3) . . ?
C2 C1 B5 111.1(3) . . ?
B4 C1 B5 61.2(2) . . ?
B3 C1 B5 114.1(3) . . ?
C19 C1 B6 122.8(3) . . ?
C2 C1 B6 61.4(3) . . ?
B4 C1 B6 110.4(3) . . ?
B3 C1 B6 114.3(3) . . ?
B5 C1 B6 61.3(3) . . ?
C11 C2 C1 111.1(5) . . ?
C11 C2 B6 113.2(5) . . ?
C1 C2 B6 60.8(3) . . ?
C11 C2 B7 131.0(6) . . ?
C1 C2 B7 107.7(4) . . ?
B6 C2 B7 111.3(4) . . ?
C11 C2 B11 128.0(5) . . ?
C1 C2 B11 107.9(4) . . ?
B6 C2 B11 60.5(3) . . ?
B7 C2 B11 62.1(2) . . ?
C11 C2 B3 117.5(5) . . ?
C1 C2 B3 59.7(2) . . ?
B6 C2 B3 111.3(4) . . ?
B7 C2 B3 61.0(2) . . ?
B11 C2 B3 111.3(3) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 B3 119.5(2) . . ?
C17 C12 B3 121.5(2) . . ?
C14 C13 C12 121.8(3) . . ?
C15 C14 C13 119.4(3) . . ?
C14 C15 C16 120.4(3) . . ?
C15 C16 C17 121.5(3) . . ?
C16 C17 C12 117.9(2) . . ?
C16 C17 C18 120.9(2) . . ?
C12 C17 C18 121.2(2) . . ?
C19 C18 C17 123.2(2) . . ?
C19 C18 C20 119.1(2) . . ?
C17 C18 C20 117.7(2) . . ?
C18 C19 C1 125.4(3) . . ?
C21 C20 C18 111.5(2) . . ?
C21 C20 C25 108.7(3) . . ?
C18 C20 C25 115.4(2) . . ?
C20 C21 C22 111.6(3) . . ?
C23 C22 C21 111.2(3) . . ?
C24 C23 C22 111.3(3) . . ?
C23 C24 C25 111.2(3) . . ?
C24 C25 C20 110.4(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B3 C12 1.534(4) . ?
B3 C1 1.702(4) . ?
B3 B4 1.733(5) . ?
B3 C2 1.750(5) . ?
B3 B7 1.766(5) . ?
B3 B8 1.780(5) . ?
B4 C11' 1.377(6) . ?
B4 C1 1.672(6) . ?
B4 B8 1.704(5) . ?
B4 B9 1.710(5) . ?
B4 B5 1.726(5) . ?
B5 C1 1.715(6) . ?
B5 B10 1.742(6) . ?
B5 B6 1.749(9) . ?
B5 B9 1.771(6) . ?
B6 C1 1.717(5) . ?
B6 C2 1.727(7) . ?
B6 B11 1.744(6) . ?
B6 B10 1.755(7) . ?
B7 C2 1.731(5) . ?
B7 B8 1.767(6) . ?
B7 B12 1.775(7) . ?
B7 B11 1.786(6) . ?
B8 B12 1.776(5) . ?
B8 B9 1.779(6) . ?
B9 B12 1.765(7) . ?
B9 B10 1.767(8) . ?
B10 B11 1.750(8) . ?
B10 B12 1.783(6) . ?
B11 C2 1.733(6) . ?
B11 B12 1.757(7) . ?
C1 C19 1.476(4) . ?
C1 C2 1.665(6) . ?
C2 C11 1.264(8) . ?
C12 C13 1.398(3) . ?
C12 C17 1.407(3) . ?
C13 C14 1.366(4) . ?
C14 C15 1.365(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.394(4) . ?
C17 C18 1.485(3) . ?
C18 C19 1.327(4) . ?
C18 C20 1.522(4) . ?
C20 C21 1.509(4) . ?
C20 C25 1.528(4) . ?
C21 C22 1.528(4) . ?
C22 C23 1.525(5) . ?
C23 C24 1.497(6) . ?
C24 C25 1.524(4) . ?
