#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:24:20 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135293.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_4135293
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            'C16 H30 B20'
_chemical_formula_weight         438.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 130.9430(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0829(2)
_cell_length_b                   24.8661(7)
_cell_length_c                   10.4140(3)
_cell_measurement_reflns_used    68
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1385.45(7)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO 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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.638
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0904P)²+0.4438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1881
_reflns_number_total             2518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3As.cif
_cod_data_source_block           3As
_cod_depositor_comments
'Adding full bibliography for 4135283--4135293.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4135293
_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   0.981
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.1701(3) 0.11112(7) 0.9842(2) 0.0367(5) Uani 1 1 d . . . . .
C2 C 0.1326(4) 0.17418(8) 1.0230(2) 0.0372(5) Uani 1 1 d . . . . .
C11 C 0.3299(4) 0.19582(10) 1.2002(3) 0.0591(7) Uani 1 1 d . . . . .
H11A H 0.2874 0.2319 1.2060 0.089 Uiso 1 1 calc R U . . .
H11B H 0.3394 0.1735 1.2795 0.089 Uiso 1 1 calc R U . . .
H11C H 0.4887 0.1959 1.2281 0.089 Uiso 1 1 calc R U . . .
C12 C 0.3886(4) 0.08232(9) 1.1223(3) 0.0477(5) Uani 1 1 d . . . . .
C13 C 0.5701(4) 0.05823(8) 1.2344(3) 0.0487(6) Uani 1 1 d . . . . .
C14 C 0.7891(4) 0.02881(8) 1.3700(2) 0.0409(5) Uani 1 1 d . . . . .
C15 C 1.0170(4) 0.03824(8) 1.4125(3) 0.0488(6) Uani 1 1 d . . . . .
H15 H 1.0288 0.0640 1.3534 0.059 Uiso 1 1 calc R U . . .
C16 C 0.7739(4) -0.00970(8) 1.4582(3) 0.0466(5) Uani 1 1 d . . . . .
H16 H 0.6216 -0.0164 1.4302 0.056 Uiso 1 1 calc R U . . .
B3 B 0.2171(4) 0.16419(10) 0.9019(3) 0.0422(6) Uani 1 1 d . . . . .
H3 H 0.3997 0.1756 0.9431 0.051 Uiso 1 1 calc R U . . .
B4 B 0.0579(4) 0.10495(9) 0.7821(3) 0.0400(5) Uani 1 1 d . . . . .
H4 H 0.1361 0.0779 0.7438 0.048 Uiso 1 1 calc R U . . .
B5 B -0.1111(4) 0.07985(9) 0.8409(3) 0.0416(6) Uani 1 1 d . . . . .
H5 H -0.1422 0.0365 0.8408 0.050 Uiso 1 1 calc R U . . .
B6 B -0.0562(4) 0.12367(10) 0.9973(3) 0.0436(6) Uani 1 1 d . . . . .
H6 H -0.0493 0.1089 1.0998 0.052 Uiso 1 1 calc R U . . .
B7 B -0.0073(5) 0.21256(10) 0.8467(3) 0.0467(6) Uani 1 1 d . . . . .
H7 H 0.0281 0.2558 0.8502 0.056 Uiso 1 1 calc R U . . .
B8 B -0.0624(5) 0.16919(10) 0.6897(3) 0.0476(6) Uani 1 1 d . . . . .
H8 H -0.0649 0.1841 0.5892 0.057 Uiso 1 1 calc R U . . .
B9 B -0.2670(4) 0.11722(10) 0.6516(3) 0.0436(6) Uani 1 1 d . . . . .
H9 H -0.4033 0.0983 0.5260 0.052 Uiso 1 1 calc R U . . .
B10 B -0.3361(4) 0.12878(11) 0.7853(3) 0.0473(6) Uani 1 1 d . . . . .
H10 H -0.5168 0.1174 0.7471 0.057 Uiso 1 1 calc R U . . .
B11 B -0.1753(4) 0.18762(10) 0.9050(3) 0.0455(6) Uani 1 1 d . . . . .
H11 H -0.2496 0.2147 0.9461 0.055 Uiso 1 1 calc R U . . .
B12 B -0.3067(5) 0.18380(11) 0.6908(3) 0.0499(7) Uani 1 1 d . . . . .
H12 H -0.4690 0.2083 0.5904 0.060 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 C1 C2 117.43(16) . . ?
C12 C1 B4 121.18(17) . . ?
C2 C1 B4 111.21(14) . . ?
C12 C1 B5 121.60(17) . . ?
C2 C1 B5 110.94(14) . . ?
B4 C1 B5 62.93(13) . . ?
C12 C1 B3 116.64(17) . . ?
C2 C1 B3 61.15(12) . . ?
B4 C1 B3 62.54(13) . . ?
B5 C1 B3 114.23(15) . . ?
C12 C1 B6 117.35(17) . . ?
C2 C1 B6 60.73(12) . . ?
B4 C1 B6 114.15(15) . . ?
B5 C1 B6 62.47(13) . . ?
B3 C1 B6 113.18(15) . . ?
C11 C2 C1 117.47(16) . . ?
C11 C2 B11 122.60(18) . . ?
C1 C2 B11 109.91(15) . . ?
C11 C2 B7 122.67(18) . . ?
C1 C2 B7 109.65(15) . . ?
B11 C2 B7 62.75(14) . . ?
C11 C2 B6 116.98(17) . . ?
C1 C2 B6 60.79(12) . . ?
B11 C2 B6 62.08(14) . . ?
B7 C2 B6 113.47(16) . . ?
C11 C2 B3 117.23(18) . . ?
C1 C2 B3 60.48(12) . . ?
B11 C2 B3 113.25(15) . . ?
B7 C2 B3 61.84(14) . . ?
B6 C2 B3 112.66(15) . . ?
C13 C12 C1 178.7(2) . . ?
C12 C13 C14 179.7(3) . . ?
C16 C14 C15 119.19(18) . . ?
C16 C14 C13 120.2(2) . . ?
C15 C14 C13 120.59(19) . . ?
C16 C15 C14 120.4(2) 3_758 . ?
C15 C16 C14 120.4(2) 3_758 . ?
C1 B3 C2 58.36(12) . . ?
C1 B3 B8 104.75(16) . . ?
C2 B3 B8 105.29(17) . . ?
C1 B3 B7 104.99(16) . . ?
C2 B3 B7 58.10(13) . . ?
B8 B3 B7 60.61(14) . . ?
C1 B3 B4 58.19(12) . . ?
C2 B3 B4 105.51(16) . . ?
B8 B3 B4 60.10(14) . . ?
B7 B3 B4 108.38(17) . . ?
C1 B4 B8 105.05(16) . . ?
C1 B4 B9 104.64(16) . . ?
B8 B4 B9 60.43(14) . . ?
C1 B4 B3 59.27(12) . . ?
B8 B4 B3 59.40(14) . . ?
B9 B4 B3 107.68(16) . . ?
C1 B4 B5 58.62(12) . . ?
B8 B4 B5 108.14(17) . . ?
B9 B4 B5 59.68(14) . . ?
B3 B4 B5 108.06(16) . . ?
C1 B5 B9 104.74(16) . . ?
C1 B5 B10 104.93(16) . . ?
B9 B5 B10 60.23(14) . . ?
C1 B5 B4 58.45(12) . . ?
B9 B5 B4 59.98(13) . . ?
B10 B5 B4 108.07(17) . . ?
C1 B5 B6 59.30(12) . . ?
B9 B5 B6 107.56(17) . . ?
B10 B5 B6 59.29(14) . . ?
B4 B5 B6 107.93(16) . . ?
C2 B6 C1 58.49(12) . . ?
C2 B6 B10 105.35(16) . . ?
C1 B6 B10 104.84(16) . . ?
C2 B6 B11 58.13(13) . . ?
C1 B6 B11 104.97(16) . . ?
B10 B6 B11 60.40(14) . . ?
C2 B6 B5 105.75(16) . . ?
C1 B6 B5 58.23(12) . . ?
B10 B6 B5 60.25(13) . . ?
B11 B6 B5 108.34(16) . . ?
C2 B7 B3 60.05(12) . . ?
C2 B7 B11 58.51(13) . . ?
B3 B7 B11 108.37(16) . . ?
C2 B7 B12 105.32(17) . . ?
B3 B7 B12 107.81(17) . . ?
B11 B7 B12 60.04(15) . . ?
C2 B7 B8 105.96(16) . . ?
B3 B7 B8 59.54(14) . . ?
B11 B7 B8 108.19(18) . . ?
B12 B7 B8 60.11(14) . . ?
B3 B8 B4 60.50(13) . . ?
B3 B8 B7 59.85(14) . . ?
B4 B8 B7 108.10(16) . . ?
B3 B8 B12 107.82(17) . . ?
B4 B8 B12 107.78(18) . . ?
B7 B8 B12 59.80(14) . . ?
B3 B8 B9 108.09(17) . . ?
B4 B8 B9 59.84(14) . . ?
B7 B8 B9 107.57(18) . . ?
B12 B8 B9 59.74(14) . . ?
B5 B9 B4 60.34(13) . . ?
B5 B9 B12 108.18(16) . . ?
B4 B9 B12 107.88(17) . . ?
B5 B9 B10 60.11(14) . . ?
B4 B9 B10 108.26(16) . . ?
B12 B9 B10 60.05(14) . . ?
B5 B9 B8 108.12(16) . . ?
B4 B9 B8 59.73(14) . . ?
B12 B9 B8 59.97(15) . . ?
B10 B9 B8 108.04(17) . . ?
B6 B10 B11 59.94(14) . . ?
B6 B10 B5 60.46(13) . . ?
B11 B10 B5 108.14(16) . . ?
B6 B10 B12 107.86(17) . . ?
B11 B10 B12 59.86(14) . . ?
B5 B10 B12 107.67(17) . . ?
B6 B10 B9 108.04(16) . . ?
B11 B10 B9 107.78(18) . . ?
B5 B10 B9 59.66(13) . . ?
B12 B10 B9 59.86(14) . . ?
C2 B11 B6 59.78(13) . . ?
C2 B11 B7 58.74(13) . . ?
B6 B11 B7 108.36(16) . . ?
C2 B11 B12 105.57(17) . . ?
B6 B11 B12 107.92(17) . . ?
B7 B11 B12 60.13(15) . . ?
C2 B11 B10 106.05(16) . . ?
B6 B11 B10 59.66(14) . . ?
B7 B11 B10 108.43(17) . . ?
B12 B11 B10 60.22(15) . . ?
B11 B12 B7 59.83(14) . . ?
B11 B12 B9 108.00(17) . . ?
B7 B12 B9 108.24(17) . . ?
B11 B12 B10 59.92(14) . . ?
B7 B12 B10 107.95(16) . . ?
B9 B12 B10 60.09(14) . . ?
B11 B12 B8 108.01(16) . . ?
B7 B12 B8 60.10(15) . . ?
B9 B12 B8 60.29(14) . . ?
B10 B12 B8 108.33(17) . . ?
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
C1 C12 1.435(3) . ?
C1 C2 1.683(3) . ?
C1 B4 1.701(3) . ?
C1 B5 1.704(3) . ?
C1 B3 1.721(3) . ?
C1 B6 1.723(3) . ?
C2 C11 1.506(3) . ?
C2 B11 1.693(3) . ?
C2 B7 1.697(3) . ?
C2 B6 1.722(3) . ?
C2 B3 1.732(3) . ?
C12 C13 1.186(3) . ?
C13 C14 1.437(3) . ?
C14 C16 1.379(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.377(3) 3_758 ?
C16 C15 1.377(3) 3_758 ?
B3 B8 1.756(3) . ?
B3 B7 1.762(3) . ?
B3 B4 1.776(3) . ?
B4 B8 1.769(3) . ?
B4 B9 1.771(3) . ?
B4 B5 1.777(3) . ?
B5 B9 1.765(3) . ?
B5 B10 1.773(3) . ?
B5 B6 1.777(3) . ?
B6 B10 1.756(3) . ?
B6 B11 1.761(3) . ?
B7 B11 1.765(4) . ?
B7 B12 1.770(4) . ?
B7 B8 1.775(4) . ?
B8 B12 1.776(4) . ?
B8 B9 1.781(4) . ?
B9 B12 1.771(3) . ?
B9 B10 1.776(3) . ?
B10 B11 1.769(4) . ?
B10 B12 1.775(4) . ?
B11 B12 1.768(3) . ?
