Heterocyclic and Open-Chain Carboranes via Transition-Metal-Free C‒H Functionalization of Mono- and Diazine-N-oxides
Galliamova, Lidiia A.; Varaksin, Mikhail V.; Chupakhin, Oleg N.; Slepukhin, Pavel A.; Charushin, Valery N.; Organometallics 34 (2015) 5285–; doi:10.1021/acs.organomet.5b00736

data_4087932
_publ_section_title
;
 Heterocyclic and Open-Chain Carboranes via Transition-Metal-Free C--H
 Functionalization of Mono- and Diazine-N-oxides
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5285
_journal_paper_doi               10.1021/acs.organomet.5b00736
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         '4(C24 H20 B10 Cu F12 N2 O4)'
_chemical_formula_sum            'C96 H80 B40 Cu4 F48 N8 O16'
_chemical_formula_weight         3200.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-07
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                93.587(2)
_cell_angle_beta                 92.779(2)
_cell_angle_gamma                94.252(2)
_cell_formula_units_Z            1
_cell_length_a                   12.3972(3)
_cell_length_b                   13.6503(3)
_cell_length_c                   19.9916(6)
_cell_measurement_reflns_used    9717
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.7540
_cell_measurement_theta_min      2.1420
_cell_volume                     3362.37(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.8690
_diffrn_measurement_details
;
  1 omega  -18.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000 -150.0000 26

  2 omega  -91.00  -66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -77.0000   90.0000 25

  3 omega  -40.00   19.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -57.0000    0.0000 59

  4 omega   13.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920   57.0000 -120.0000 79

  5 omega   -6.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920   77.0000   90.0000 99

  6 omega   21.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920   57.0000 -180.0000 57

  7 omega  -25.00   63.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -99.0000  -30.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0052144000
_diffrn_orient_matrix_UB_12      -0.0501421000
_diffrn_orient_matrix_UB_13      -0.0099669000
_diffrn_orient_matrix_UB_21      0.0321935000
_diffrn_orient_matrix_UB_22      0.0145779000
_diffrn_orient_matrix_UB_23      -0.0265730000
_diffrn_orient_matrix_UB_31      0.0473011000
_diffrn_orient_matrix_UB_32      0.0005167000
_diffrn_orient_matrix_UB_33      0.0214922000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            33657
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.83
_diffrn_reflns_theta_min         1.89
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1588
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.117
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1036
_refine_ls_number_reflns         18353
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1050P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1654
_reflns_number_gt                13832
_reflns_number_total             18353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00736_si_002.cif
_cod_data_source_block           exp_423
_cod_database_code               4087932
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22