Sonogashira Coupling of the Ethynyl Monocarborane [CB11H11-12-CCH]–
Duttwyler, Simon; Liu, Fan; Chen, Tao; Zhang, Kang; Jiang, Tao; Liu, Jiyong; Dalton Transactions  (2022) –; doi:10.1039/D2DT01048H

data_7710622
_publ_section_title
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 Sonogashira Coupling of the Ethynyl Monocarborane [CB11H11-12-CCH]--
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_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01048H
_journal_year                    2022
_chemical_formula_moiety         'C8 H15 B11 N, C8 H20 N'
_chemical_formula_sum            'C16 H35 B11 N2'
_chemical_formula_weight         374.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.226(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8925(10)
_cell_length_b                   22.8056(10)
_cell_length_c                   11.5812(6)
_cell_measurement_reflns_used    9268
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.45
_cell_volume                     4706.1(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            72768
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.768
_diffrn_reflns_theta_min         1.979
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1558 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.9257.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         10014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0613
_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/[\s^2^(Fo^2^)+(0.0827P)^2^+1.7231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6664
_reflns_number_total             10014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01048h2.cif
_cod_data_source_block           mo_210524_et4n_py
_cod_database_code               7710622
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.976
_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:
 C9(H9B,H9C), C11(H11B,H11C), C13(H13A,H13B), C15(H15A,H15B), C9A(H9AA,H9AB),
 C11A(H11D,H11E), C13A(H13C,H13D), C15A(H15C,H15D)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C5A(H5AA), C6A(H6AA), C7A(H7AA), C8A(H8AA)
2.c Idealised Me refined as rotating group:
 C10(H10B,H10C,H10D), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C10A(H10E,H10F,H10G), C12A(H12D,H12E,H12F), C14A(H14D,H14E,H14F),
 C16A(H16D,H16E,H16F)
2.d Boron cage BH refined with riding coordinates:
 C1(H1), B2(H2), B3(H3), B4(H4), B5(H5A), B6(H6A), B7(H7A), B8(H8A), B9(H9),
 B10(H10), B11(H11), C1A(H1A), B2A(H2A), B3A(H3A), B4A(H4A), B5A(H5AB),
 B6A(H6AB), B7A(H7AB), B8A(H8AB), B9A(H9A), B10A(H10A), B11A(H11A)
;
_shelx_res_checksum              2354
_shelx_hkl_checksum              55472
_olex2_submission_special_instructions 'No special instructions were received'