A facile approach for synthesis of nido-carborane fused oxazoles via one pot deboronation/cyclization of 9-amide-o-carboranes
Zhang, Cai-Yan; Cao, Ke; Xu, Tao-Tao; Wu, Ji; Jiang, Lin-Hai; Yang, Junxiao; Chemical Communications  (2018) –; doi:10.1039/C8CC07728B

data_7122728
_publ_section_title
;
 A facile approach for synthesis of nido-carborane fused oxazoles via one
 pot deboronation/cyclization of 9-amide-o-carboranes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC07728B
_journal_year                    2018
_chemical_formula_moiety         'C22 H40 B18 Cs2 N2 O2'
_chemical_formula_sum            'C22 H40 B18 Cs2 N2 O2'
_chemical_formula_weight         824.96
_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   mixed
_atom_sites_solution_primary     heavy
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-07-02 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                108.368(7)
_cell_angle_beta                 92.326(6)
_cell_angle_gamma                94.863(6)
_cell_formula_units_Z            2
_cell_length_a                   9.9229(8)
_cell_length_b                   13.5206(9)
_cell_length_c                   14.4241(11)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    292.78(10)
_cell_measurement_theta_max      27.5610
_cell_measurement_theta_min      3.5250
_cell_volume                     1825.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     72.00  99.00   1.50    2.50    --   25.05  57.00-120.00   18
  2  \w     31.00  97.00   1.50    2.50    --   25.05  57.00-150.00   44
  3  \w     22.00  74.50   1.50    2.50    --   25.05 -99.00-120.00   35
  4  \w     87.00 112.50   1.50    2.50    --   25.05-178.00-150.00   17
  5  \w    -44.00  55.00   1.50    2.50    --   25.05 -57.00  90.00   66
  6  \w    -33.00  51.00   1.50    2.50    --  -22.08  57.00 -30.00   56
  7  \w     36.00 109.50   1.50    2.50    --   25.05 178.00 120.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0480130000
_diffrn_orient_matrix_UB_12      -0.0077247000
_diffrn_orient_matrix_UB_13      0.0342025000
_diffrn_orient_matrix_UB_21      0.0526452000
_diffrn_orient_matrix_UB_22      0.0046542000
_diffrn_orient_matrix_UB_23      -0.0306564000
_diffrn_orient_matrix_UB_31      0.0097945000
_diffrn_orient_matrix_UB_32      0.0548350000
_diffrn_orient_matrix_UB_33      0.0242646000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.418
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.023
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7171
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0246P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5584
_reflns_number_total             7171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07728b3.cif
_cod_data_source_block           caok_195
_cod_original_cell_volume        1825.4(2)
_cod_database_code               7122728
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.68
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C7A, B9}
{B9A, C7}
3. Restrained distances
 B3A-H3A
 1 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C7A) = Uanis(B9)
Uanis(B9A) = Uanis(C7)
5. Others
 Fixed Sof: C7(0.75) C12(0.75) B3'(0.6) H3'(0.6) B9(0.75) C7A(0.25) C12A(0.25)
 B3A(0.4) H3A(0.4) B9A(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C16'(H16'), C17(H17), C17'(H17'), C18(H18), C18'(H18'), C19(H19),
 C19'(H19'), C20(H20), C20'(H20')
6.b Idealised Me refined as rotating group:
 C12'(H12A,H12B,H12C), C13(H13A,H13B,H13C), C13'(H13D,H13E,H13F), C12(H12D,
 H12E,H12F)
6.c Boron cage BH refined with riding coordinates:
 B3'(H3')
;
_olex2_date_sample_data_collection 2018-02-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.147
_oxdiff_exptl_absorpt_empirical_full_min 0.879