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_7122727
_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         'C9 H16 B9 N O'
_chemical_formula_sum            'C9 H16 B9 N O'
_chemical_formula_weight         251.52
_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     direct
_audit_creation_date             2018-04-27
_audit_creation_method
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Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-07-02 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.954(13)
_cell_angle_beta                 90.958(13)
_cell_angle_gamma                105.754(16)
_cell_formula_units_Z            2
_cell_length_a                   6.7060(12)
_cell_length_b                   10.2830(19)
_cell_length_c                   10.2838(14)
_cell_measurement_reflns_used    1038
_cell_measurement_temperature    290.38(10)
_cell_measurement_theta_max      27.0380
_cell_measurement_theta_min      3.8260
_cell_volume                     682.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_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      290.38(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -1.00   26.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   30.0000 18

  2 omega   16.00   53.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -120.0000 25

  3 omega  -48.00   43.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000   30.0000 61

  4 omega   -5.00   25.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   30.0000 20

  5 omega  -48.00   45.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 62

  6 omega  -45.00   45.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -120.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1034335000
_diffrn_orient_matrix_UB_12      0.0335758000
_diffrn_orient_matrix_UB_13      0.0193858000
_diffrn_orient_matrix_UB_21      0.0317928000
_diffrn_orient_matrix_UB_22      -0.0577205000
_diffrn_orient_matrix_UB_23      -0.0192380000
_diffrn_orient_matrix_UB_31      0.0193497000
_diffrn_orient_matrix_UB_32      0.0260786000
_diffrn_orient_matrix_UB_33      -0.0633633000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4266
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.691
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.3490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1877
_reflns_number_total             2680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07728b2.cif
_cod_data_source_block           zcy_087
_cod_original_cell_volume        682.3(2)
_cod_database_code               7122727
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.78
_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, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Boron cage BH refined with riding coordinates:
 B1(H1A), B2(H2), B3(H3), B4(H4), B5(H5)
;
_olex2_date_sample_data_collection 2017-06-16
_olex2_submission_special_instructions 'No special instructions were received'