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_7230948
_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         '2(C6 H30 B22 N2 Na O4), 2(C8 H20 N)'
_chemical_formula_sum            'C28 H100 B44 N6 Na2 O8'
_chemical_formula_weight         1170.76
_chemical_name_systematic
;
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                88.511(6)
_cell_angle_beta                 89.235(4)
_cell_angle_gamma                85.054(5)
_cell_formula_units_Z            2
_cell_length_a                   7.6610(3)
_cell_length_b                   14.6847(11)
_cell_length_c                   30.005(2)
_cell_measurement_reflns_used    5385
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.4816
_cell_measurement_theta_min      2.7798
_cell_volume                     3361.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0067563000
_diffrn_orient_matrix_UB_12      -0.0415150000
_diffrn_orient_matrix_UB_13      0.0122542000
_diffrn_orient_matrix_UB_21      -0.0029565000
_diffrn_orient_matrix_UB_22      -0.0237624000
_diffrn_orient_matrix_UB_23      -0.0202312000
_diffrn_orient_matrix_UB_31      0.0926429000
_diffrn_orient_matrix_UB_32      -0.0079699000
_diffrn_orient_matrix_UB_33      -0.0000136000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22672
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     805
_refine_ls_number_reflns         12230
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.1413
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+25.5966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2968
_refine_ls_wR_factor_ref         0.3087
_reflns_number_gt                9444
_reflns_number_total             12230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra03067g2.cif
_cod_data_source_block           150603_pyn_1
_cod_database_code               7230948
_chemical_oxdiff_formula         'c10 h10 B2 O8 B1'
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C5 \\sim N2 \\sim O4 \\sim C6: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,
 H21B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3D), N4(H4A)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C28(H28A,
 H28B,H28C)
3.d Boron cage BH refined with riding coordinates:
 B1(H1A), B2(H2A), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9),
 B10(H10), B11(H11), B12(H12), B13(H13), B14(H14), B15(H15), B16(H16), B17(H17),
  B18(H18), B19(H19), B20(H20), B21(H21), B22(H22), B23(H23), B24(H24),
 B25(H25), B26(H26), B27(H27), B28(H28), B29(H29), B30(H30), B31(H31), B32(H32),
  B33(H33), B34(H34), B35(H35), B36(H36), B37(H37), B38(H38), B39(H39),
 B40(H40), B41(H41), B42(H42), B43(H43), B44(H44)
;