Efficient access to amides of the carborane carboxylic acid [1-(COOH)‒CB11H11]−
Shen, Yunjun; Zheng, Kai; Dontha, Rakesh; Pan, Yani; Liu, Jiyong; Duttwyler, Simon; RSC Advances 8 (2018) 22447–; doi:10.1039/C8RA03067G

data_7230949
_publ_section_title
;
 Efficient access to amides of the carborane carboxylic acid
 [1-(COOH)--CB11H11]&#x2212;
;
_journal_issue                   40
_journal_name_full               'RSC Advances'
_journal_page_first              22447
_journal_paper_doi               10.1039/C8RA03067G
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C8 H16 B11 I N O, C8 H20 N'
_chemical_formula_sum            'C16 H36 B11 I N2 O'
_chemical_formula_weight         518.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                71.718(3)
_cell_angle_beta                 83.920(4)
_cell_angle_gamma                72.759(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1861(5)
_cell_length_b                   11.3166(6)
_cell_length_c                   13.6234(6)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.656
_cell_measurement_theta_min      4.019
_cell_volume                     1284.19(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      170.01
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13350
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.958
_diffrn_reflns_theta_min         2.972
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.601
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.3734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1603 before and 0.0913 after correction. The Ratio of minimum to maximum transmission is 0.4973. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.853
_refine_diff_density_min         -1.567
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.0051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1127P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3609
_reflns_number_total             4856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra03067g2.cif
_cod_data_source_block           mjl18067_0m
_cod_database_code               7230949
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.734
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C)
2.d Boron cage BH refined with riding coordinates:
 B2(H2), B3(H3), B4(H4A), B5(H5A), B6(H6), B7(H7A), B8(H8A), B9(H9), B10(H10),
 B11(H11), B12(H12)
;
_shelx_res_checksum              4314
_olex2_submission_special_instructions 'No special instructions were received'