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_4087933
_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         'C21 H19 B10 Cu F9 N2 O4'
_chemical_formula_sum            'C21 H19 B10 Cu F9 N2 O4'
_chemical_formula_weight         706.02
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-16
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.309(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9262(4)
_cell_length_b                   19.0285(4)
_cell_length_c                   12.8975(3)
_cell_measurement_reflns_used    4722
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.8520
_cell_measurement_theta_min      2.2460
_cell_volume                     2926.89(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9852
_diffrn_measured_fraction_theta_max 0.8598
_diffrn_measurement_details
;
  1 omega  -18.00    8.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000  -60.0000 26

  2 omega  -50.00   -6.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360   77.0000  120.0000 44

  3 omega    2.00   94.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   38.0000  -30.0000 92

  4 omega  -25.00    1.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000 -180.0000 26

  5 omega  -11.00   63.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362   19.0000  -90.0000 74
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0526707000
_diffrn_orient_matrix_UB_12      -0.0065718000
_diffrn_orient_matrix_UB_13      0.0234256000
_diffrn_orient_matrix_UB_21      0.0258189000
_diffrn_orient_matrix_UB_22      0.0008474000
_diffrn_orient_matrix_UB_23      0.0496354000
_diffrn_orient_matrix_UB_31      -0.0100277000
_diffrn_orient_matrix_UB_32      0.0366763000
_diffrn_orient_matrix_UB_33      0.0030855000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17535
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.88
_diffrn_reflns_theta_min         2.32
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7951
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0800P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                5741
_reflns_number_total             7951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00736_si_002.cif
_cod_data_source_block           exp_430
_cod_original_cell_volume        2926.88(13)
_cod_database_code               4087933
_chemical_oxdiff_formula         C10H10NO
_reflns_odcompleteness_completeness 98.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22