#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:24:20 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135287.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_4135287
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            'C15 H20 B10'
_chemical_formula_weight         308.41
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 95.3224(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0460(3)
_cell_length_b                   7.8624(2)
_cell_length_c                   15.3076(3)
_cell_measurement_reflns_used    142
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1803.05(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.815
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6693
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0503
_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)+(0.0771P)²+0.5775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2776
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3At.cif
_cod_data_source_block           3At
_cod_depositor_comments
'Adding full bibliography for 4135283--4135293.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4135287
_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   0.978
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.79070(11) 0.7717(2) 1.08609(10) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.81163(10) 0.72055(19) 0.98315(10) 0.0351(4) Uani 1 1 d . . . . .
C11 C 0.80280(16) 0.9546(2) 1.11439(13) 0.0616(6) Uani 1 1 d . . . . .
H11A H 0.7888 0.9663 1.1740 0.092 Uiso 1 1 calc R U . . .
H11B H 0.8636 0.9882 1.1101 0.092 Uiso 1 1 calc R U . . .
H11C H 0.7637 1.0257 1.0771 0.092 Uiso 1 1 calc R U . . .
C12 C 0.84086(11) 0.8511(2) 0.92662(11) 0.0421(4) Uani 1 1 d . . . . .
C13 C 0.86517(11) 0.9493(2) 0.87491(11) 0.0424(4) Uani 1 1 d . . . . .
C14 C 0.89870(11) 1.0611(2) 0.81103(10) 0.0391(4) Uani 1 1 d . . . . .
C15 C 0.86461(11) 1.2209(2) 0.79594(10) 0.0393(4) Uani 1 1 d . . . . .
H15A H 0.8173 1.2575 0.8261 0.047 Uiso 1 1 calc R U . . .
C16 C 0.90043(11) 1.3318(2) 0.73484(10) 0.0380(4) Uani 1 1 d . . . . .
C17 C 0.86781(14) 1.4980(2) 0.71985(12) 0.0514(5) Uani 1 1 d . . . . .
H17A H 0.8205 1.5370 0.7493 0.062 Uiso 1 1 calc R U . . .
C18 C 0.90542(15) 1.6021(3) 0.66212(13) 0.0617(6) Uani 1 1 d . . . . .
H18A H 0.8830 1.7113 0.6521 0.074 Uiso 1 1 calc R U . . .
C19 C 0.97746(14) 1.5460(3) 0.61788(13) 0.0615(6) Uani 1 1 d . . . . .
H19A H 1.0035 1.6193 0.5799 0.074 Uiso 1 1 calc R U . . .
C20 C 1.00940(13) 1.3861(3) 0.63000(12) 0.0569(5) Uani 1 1 d . . . . .
H20A H 1.0565 1.3497 0.5995 0.068 Uiso 1 1 calc R U . . .
C21 C 0.97158(11) 1.2730(2) 0.68901(10) 0.0421(4) Uani 1 1 d . . . . .
C22 C 1.00386(12) 1.1069(3) 0.70415(12) 0.0514(5) Uani 1 1 d . . . . .
H22A H 1.0497 1.0670 0.6729 0.062 Uiso 1 1 calc R U . . .
C23 C 0.96932(12) 1.0033(2) 0.76363(12) 0.0480(4) Uani 1 1 d . . . . .
H23A H 0.9921 0.8943 0.7732 0.058 Uiso 1 1 calc R U . . .
B3 B 0.88592(12) 0.6570(2) 1.07000(13) 0.0412(4) Uani 1 1 d . . . . .
H3 H 0.9542 0.7066 1.0833 0.049 Uiso 1 1 calc R U . . .
B4 B 0.81854(14) 0.6067(3) 1.15502(12) 0.0437(5) Uani 1 1 d . . . . .
H4 H 0.8435 0.6219 1.2244 0.052 Uiso 1 1 calc R U . . .
B5 B 0.70577(14) 0.6502(3) 1.11715(13) 0.0459(5) Uani 1 1 d . . . . .
H5 H 0.6575 0.6936 1.1621 0.055 Uiso 1 1 calc R U . . .
B6 B 0.70261(12) 0.7279(3) 1.00839(12) 0.0418(4) Uani 1 1 d . . . . .
H6 H 0.6536 0.8232 0.9823 0.050 Uiso 1 1 calc R U . . .
B7 B 0.85480(13) 0.5208(2) 0.97987(13) 0.0409(4) Uani 1 1 d . . . . .
H7 H 0.9036 0.4804 0.9348 0.049 Uiso 1 1 calc R U . . .
B8 B 0.85772(14) 0.4436(2) 1.08857(13) 0.0456(5) Uani 1 1 d . . . . .
H8 H 0.9081 0.3508 1.1147 0.055 Uiso 1 1 calc R U . . .
B9 B 0.74607(14) 0.4387(3) 1.11792(13) 0.0457(5) Uani 1 1 d . . . . .
H9 H 0.7238 0.3424 1.1633 0.055 Uiso 1 1 calc R U . . .
B10 B 0.67424(13) 0.5142(3) 1.02697(13) 0.0469(5) Uani 1 1 d . . . . .
H10 H 0.6054 0.4676 1.0132 0.056 Uiso 1 1 calc R U . . .
B11 B 0.74140(13) 0.5639(2) 0.94186(12) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.7167 0.5512 0.8723 0.048 Uiso 1 1 calc R U . . .
B12 B 0.76850(14) 0.3859(2) 1.00932(13) 0.0453(5) Uani 1 1 d . . . . .
H12 H 0.7610 0.2553 0.9839 0.054 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
C11 C1 C2 117.93(14) . . ?
C11 C1 B5 122.00(15) . . ?
C2 C1 B5 109.79(13) . . ?
C11 C1 B4 122.22(15) . . ?
C2 C1 B4 110.00(12) . . ?
B5 C1 B4 62.96(11) . . ?
C11 C1 B3 117.29(16) . . ?
C2 C1 B3 60.86(10) . . ?
B5 C1 B3 113.66(13) . . ?
B4 C1 B3 62.03(11) . . ?
C11 C1 B6 116.82(15) . . ?
C2 C1 B6 60.49(10) . . ?
B5 C1 B6 62.13(11) . . ?
B4 C1 B6 113.81(13) . . ?
B3 C1 B6 112.95(13) . . ?
C12 C2 C1 119.14(13) . . ?
C12 C2 B7 120.15(13) . . ?
C1 C2 B7 110.67(12) . . ?
C12 C2 B11 120.41(14) . . ?
C1 C2 B11 110.85(12) . . ?
B7 C2 B11 63.12(11) . . ?
C12 C2 B6 117.53(13) . . ?
C1 C2 B6 61.12(10) . . ?
B7 C2 B6 114.33(12) . . ?
B11 C2 B6 62.40(11) . . ?
C12 C2 B3 117.20(14) . . ?
C1 C2 B3 60.87(10) . . ?
B7 C2 B3 62.28(11) . . ?
B11 C2 B3 114.23(12) . . ?
B6 C2 B3 113.50(12) . . ?
C13 C12 C2 174.77(18) . . ?
C12 C13 C14 176.56(19) . . ?
C15 C14 C23 119.69(15) . . ?
C15 C14 C13 121.70(15) . . ?
C23 C14 C13 118.60(16) . . ?
C14 C15 C16 121.02(15) . . ?
C17 C16 C21 119.52(15) . . ?
C17 C16 C15 121.95(15) . . ?
C21 C16 C15 118.52(15) . . ?
C18 C17 C16 120.19(19) . . ?
C17 C18 C19 120.66(19) . . ?
C20 C19 C18 120.47(17) . . ?
C19 C20 C21 120.65(19) . . ?
C22 C21 C16 119.30(15) . . ?
C22 C21 C20 122.20(17) . . ?
C16 C21 C20 118.48(17) . . ?
C23 C22 C21 121.27(16) . . ?
C22 C23 C14 120.16(17) . . ?
C2 B3 C1 58.27(9) . . ?
C2 B3 B8 104.55(13) . . ?
C1 B3 B8 104.99(13) . . ?
C2 B3 B4 104.88(12) . . ?
C1 B3 B4 58.16(10) . . ?
B8 B3 B4 60.30(11) . . ?
C2 B3 B7 58.10(10) . . ?
C1 B3 B7 105.25(13) . . ?
B8 B3 B7 60.02(11) . . ?
B4 B3 B7 108.04(14) . . ?
C1 B4 B3 59.82(10) . . ?
C1 B4 B8 105.78(13) . . ?
B3 B4 B8 59.67(11) . . ?
C1 B4 B9 105.13(13) . . ?
B3 B4 B9 107.98(14) . . ?
B8 B4 B9 60.25(12) . . ?
C1 B4 B5 58.48(10) . . ?
B3 B4 B5 108.23(13) . . ?
B8 B4 B5 108.10(14) . . ?
B9 B4 B5 59.85(12) . . ?
C1 B5 B9 105.32(13) . . ?
C1 B5 B6 59.85(10) . . ?
B9 B5 B6 108.06(14) . . ?
C1 B5 B4 58.56(10) . . ?
B9 B5 B4 60.02(11) . . ?
B6 B5 B4 108.37(13) . . ?
C1 B5 B10 105.95(13) . . ?
B9 B5 B10 60.39(12) . . ?
B6 B5 B10 59.65(11) . . ?
B4 B5 B10 108.45(14) . . ?
C2 B6 C1 58.39(10) . . ?
C2 B6 B10 104.73(13) . . ?
C1 B6 B10 105.07(13) . . ?
C2 B6 B5 104.86(13) . . ?
C1 B6 B5 58.02(10) . . ?
B10 B6 B5 60.33(11) . . ?
C2 B6 B11 58.38(10) . . ?
C1 B6 B11 105.49(13) . . ?
B10 B6 B11 59.85(11) . . ?
B5 B6 B11 107.89(13) . . ?
C2 B7 B12 104.77(13) . . ?
C2 B7 B8 105.39(13) . . ?
B12 B7 B8 60.55(11) . . ?
C2 B7 B3 59.62(10) . . ?
B12 B7 B3 108.12(13) . . ?
B8 B7 B3 59.60(11) . . ?
C2 B7 B11 58.54(10) . . ?
B12 B7 B11 59.60(11) . . ?
B8 B7 B11 108.16(13) . . ?
B3 B7 B11 108.33(13) . . ?
B3 B8 B7 60.39(11) . . ?
B3 B8 B4 60.03(11) . . ?
B7 B8 B4 108.12(13) . . ?
B3 B8 B9 107.99(13) . . ?
B7 B8 B9 107.68(14) . . ?
B4 B8 B9 59.90(11) . . ?
B3 B8 B12 108.07(13) . . ?
B7 B8 B12 59.71(11) . . ?
B4 B8 B12 107.78(14) . . ?
B9 B8 B12 59.82(11) . . ?
B5 B9 B4 60.12(11) . . ?
B5 B9 B12 107.94(13) . . ?
B4 B9 B12 108.02(14) . . ?
B5 B9 B8 107.99(14) . . ?
B4 B9 B8 59.85(11) . . ?
B12 B9 B8 60.18(12) . . ?
B5 B9 B10 59.97(12) . . ?
B4 B9 B10 108.19(13) . . ?
B12 B9 B10 60.06(11) . . ?
B8 B9 B10 108.28(13) . . ?
B6 B10 B11 60.39(10) . . ?
B6 B10 B5 60.02(11) . . ?
B11 B10 B5 108.08(14) . . ?
B6 B10 B12 107.88(13) . . ?
B11 B10 B12 59.68(11) . . ?
B5 B10 B12 107.45(14) . . ?
B6 B10 B9 107.76(14) . . ?
B11 B10 B9 107.64(14) . . ?
B5 B10 B9 59.64(11) . . ?
B12 B10 B9 59.77(11) . . ?
C2 B11 B12 104.73(13) . . ?
C2 B11 B10 105.31(13) . . ?
B12 B11 B10 60.61(11) . . ?
C2 B11 B6 59.22(10) . . ?
B12 B11 B6 108.12(13) . . ?
B10 B11 B6 59.76(11) . . ?
C2 B11 B7 58.34(10) . . ?
B12 B11 B7 59.75(11) . . ?
B10 B11 B7 108.24(13) . . ?
B6 B11 B7 107.84(13) . . ?
B11 B12 B7 60.65(10) . . ?
B11 B12 B9 107.99(14) . . ?
B7 B12 B9 107.85(14) . . ?
B11 B12 B10 59.71(11) . . ?
B7 B12 B10 108.24(14) . . ?
B9 B12 B10 60.17(11) . . ?
B11 B12 B8 108.36(13) . . ?
B7 B12 B8 59.75(11) . . ?
B9 B12 B8 60.00(12) . . ?
B10 B12 B8 108.22(14) . . ?
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 C11 1.508(2) . ?
C1 C2 1.684(2) . ?
C1 B5 1.698(3) . ?
C1 B4 1.700(2) . ?
C1 B3 1.730(2) . ?
C1 B6 1.731(3) . ?
C2 C12 1.438(2) . ?
C2 B7 1.702(2) . ?
C2 B11 1.706(2) . ?
C2 B6 1.721(2) . ?
C2 B3 1.729(2) . ?
C12 C13 1.187(2) . ?
C13 C14 1.440(2) . ?
C14 C15 1.369(2) . ?
C14 C23 1.416(2) . ?
C15 C16 1.421(2) . ?
C16 C17 1.407(2) . ?
C16 C21 1.411(2) . ?
C17 C18 1.365(3) . ?
C18 C19 1.401(3) . ?
C19 C20 1.353(3) . ?
C20 C21 1.424(2) . ?
C21 C22 1.405(3) . ?
C22 C23 1.360(2) . ?
B3 B8 1.761(3) . ?
B3 B4 1.767(3) . ?
B3 B7 1.775(3) . ?
B4 B8 1.772(3) . ?
B4 B9 1.773(3) . ?
B4 B5 1.775(3) . ?
B5 B9 1.770(3) . ?
B5 B6 1.770(3) . ?
B5 B10 1.776(3) . ?
B6 B10 1.764(3) . ?
B6 B11 1.775(3) . ?
B7 B12 1.767(3) . ?
B7 B8 1.768(3) . ?
B7 B11 1.783(3) . ?
B8 B9 1.779(3) . ?
B8 B12 1.782(3) . ?
B9 B12 1.776(3) . ?
B9 B10 1.783(3) . ?
B10 B11 1.765(3) . ?
B10 B12 1.781(3) . ?
B11 B12 1.765(3) . ?
