Metal-Free Peralkylation of the closo-Hexaborate Anion
Axtell, Jonathan C.; Kirlikovali, Kent O.; Jung, Dahee; Dziedzic, Rafal M.; Rheingold, Arnold L.; Spokoyny, Alexander M.; Organometallics 36 (2017) 1204–; doi:10.1021/acs.organomet.7b00078

data_4087178
_publ_section_title
;
 Metal-Free Peralkylation of the closo-Hexaborate Anion
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1204
_journal_paper_doi               10.1021/acs.organomet.7b00078
_journal_volume                  36
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H37 B6 Br6, C16 H36 N'
_chemical_formula_sum            'C58 H73 B6 Br6 N'
_chemical_formula_weight         1328.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.865(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7455(18)
_cell_length_b                   15.5711(13)
_cell_length_c                   20.7630(19)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.951
_cell_measurement_theta_min      3.563
_cell_volume                     5931.0(9)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0403
_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       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            104889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.197
_diffrn_reflns_theta_min         2.174
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.158
_exptl_absorpt_correction_T_max  0.3220
_exptl_absorpt_correction_T_min  0.1664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1209 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.5168.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       plate
_exptl_crystal_F_000             2672
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.549(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1291
_refine_ls_number_reflns         22152
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0375P)^2^+3.1969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                20516
_reflns_number_total             22152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om7b00078_si_002.cif
_cod_data_source_block           spok57_0m_a
_cod_depositor_comments          'Adding full bibliography for 4087178.cif.'
_cod_database_code               4087178
_shelx_estimated_absorpt_t_max   0.714
_shelx_estimated_absorpt_t_min   0.326
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.451(13) 0.549(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 B9-H8A
 1.18 with sigma of 0.001
 B7-H8A
 1.18 with sigma of 0.001
 B8-H8A
 1.18 with sigma of 0.001
4. Others
 Fixed Uiso: H8A(0.1) H3(0.1)
 Fixed X: H3(1.023801)
 Fixed Y: H3(0.5169)
 Fixed Z: H3(0.8145)
5.a Secondary CH2 refined with riding coordinates:
 C70(H70A,H70B), C101(H10D,H10E), C97(H97A,H97B), C84(H84A,H84B), C87(H87A,
 H87B), C103(H10F,H10G), C99(H99A,H99B), C93(H93A,H93B), C98(H98A,H98B),
 C95(H95A,H95B), C107(H10H,H10I), C28(H28A,H28B), C106(H10M,H10N), C14(H14A,
 H14B), C35(H35A,H35B), C77(H77A,H77B), C109(H10O,H10P), C42(H42A,H42B),
 C105(H10Q,H10R), C86(H86A,H86B), C89(H89A,H89B), C113(H11A,H11B), C63(H63A,
 H63B), C111(H11F,H11G), C85(H85A,H85B), C7(H7A,H7B), C110(H11H,H11I), C21(H21A,
 H21B), C56(H56A,H56B), C94(H94A,H94B), C102(H10S,H10T), C115(H11J,H11K),
 C90(H90A,H90B), C114(H11L,H11M), C91(H91A,H91B), C49(H49A,H49B)
5.b Aromatic/amide H refined with riding coordinates:
 C58(H58), C16(H16), C64(H64), C57(H57), C43(H43), C46(H46), C9(H9), C22(H22),
 C68(H68), C79(H79), C53(H53), C72(H72), C61(H61), C40(H40), C39(H39), C18(H18),
  C36(H36), C54(H54), C50(H50), C37(H37), C5(H5), C2(H2), C67(H67), C51(H51),
 C60(H60), C81(H81), C33(H33), C19(H19), C26(H26), C3(H3A), C47(H47), C65(H65),
 C11(H11), C71(H71), C15(H15), C44(H44), C6(H6), C25(H25), C8(H8), C32(H32),
 C74(H74), C23(H23), C75(H75), C12(H12), C30(H30), C82(H82), C78(H78), C29(H29)
5.c Idealised Me refined as rotating group:
 C104(H10J,H10K,H10L), C96(H96A,H96B,H96C), C112(H11C,H11D,H11E), C100(H10A,
 H10B,H10C), C88(H88A,H88B,H88C), C92(H92A,H92B,H92C), C116(H11N,H11O,H11P),
 C108(H10U,H10V,H10W)
;
_shelx_res_checksum              24807
_shelx_hkl_checksum              72241
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'