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_7122730
_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         'C11 H20 B9 N O'
_chemical_formula_sum            'C11 H20 B9 N O'
_chemical_formula_weight         279.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-30
_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                90
_cell_angle_beta                 92.738(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.0490(13)
_cell_length_b                   10.6495(7)
_cell_length_c                   16.0380(9)
_cell_measurement_reflns_used    1742
_cell_measurement_temperature    295.62(10)
_cell_measurement_theta_max      26.4690
_cell_measurement_theta_min      3.2990
_cell_volume                     3249.8(4)
_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
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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    '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_temperature      295.62(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   46.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327  178.0000   30.0000 70

  2 omega   35.00   61.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327 -178.0000  -30.0000 26

  3 omega   18.00   74.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327  -99.0000   60.0000 56

  4 omega  -36.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327   19.0000  150.0000 128
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0218887000
_diffrn_orient_matrix_UB_12      0.0539199000
_diffrn_orient_matrix_UB_13      0.0002088000
_diffrn_orient_matrix_UB_21      -0.0293100000
_diffrn_orient_matrix_UB_22      0.0384367000
_diffrn_orient_matrix_UB_23      0.0081549000
_diffrn_orient_matrix_UB_31      0.0071688000
_diffrn_orient_matrix_UB_32      -0.0074780000
_diffrn_orient_matrix_UB_33      0.0434944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6539
_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         26.019
_diffrn_reflns_theta_min         3.319
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85024
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0670
_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^)+(0.0564P)^2^+2.8287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2125
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07728b4.cif
_cod_data_source_block           zcy199up
_cod_database_code               7122730
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.66
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
2.c Boron cage BH refined with riding coordinates:
 B1(H1A), B2(H2), B3(H3), B4(H4), B5(H5)
;
_olex2_date_sample_data_collection 2018-05-10
_olex2_submission_special_instructions 'No special instructions were received'