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_7710619
_publ_section_title
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 Sonogashira Coupling of the Ethynyl Monocarborane [CB11H11-12-CCH]--
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01048H
_journal_year                    2022
_chemical_formula_moiety         'C8 H20 N, C10 H18 B11'
_chemical_formula_sum            'C18 H38 B11 N'
_chemical_formula_weight         387.40
_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     dual
_audit_creation_date             2018-12-19
_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                 106.7050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8067(2)
_cell_length_b                   24.6376(8)
_cell_length_c                   11.8907(4)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.44
_cell_volume                     2471.11(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26010
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.435
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8768.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.661
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         6132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0780P)^2^+0.3200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4987
_reflns_number_total             6132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01048h2.cif
_cod_data_source_block           181218_zk_4ch3py_0m
_cod_database_code               7710619
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.966
_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:
 C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C10(H10A,H10B,H10C)
2.d Boron cage BH refined with riding coordinates:
 C1(H1), B2(H2), B3(H3), B4(H4), B5(H5A), B6(H6A), B7(H7), B8(H8A), B9(H9A),
 B10(H10), B11(H11)
;
_shelx_res_checksum              27726
_shelx_hkl_checksum              8373
_olex2_submission_special_instructions 'No special instructions were received'