Synthesis of Benzofused 1,4-Azaborinols via [4+2] Annulation Strategy and its Application in Indole Synthesis
Chinnapattu, Murugan; Sathiyanarayanan, Kulathu Iyer; Iyer, Pravin S.; RSC Adv.  (2015) –; doi:10.1039/C5RA05082K

data_7220190
_publ_section_title
;
 Synthesis of Benzofused 1,4-Azaborinols via [4+2] Annulation Strategy and
 its Application in Indole Synthesis
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA05082K
_journal_year                    2015
_chemical_compound_source        no
_chemical_formula_moiety         'C12 H12 B N O5'
_chemical_formula_sum            'C12 H12 B N O5'
_chemical_formula_weight         261.04
_chemical_melting_point          400.0(10)
_chemical_name_common            azaborneol
_chemical_name_systematic
'Dimethyl 4-hydroxy-1,4-dihydrobenzo(b)[1,4]azaborinine-2,3-dicarboxylate'
_chemical_properties_physical    nil
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-09-19 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.367(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7056(3)
_cell_length_b                   4.76590(10)
_cell_length_c                   26.0338(8)
_cell_measurement_temperature    296(2)
_cell_volume                     1196.79(6)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9052
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.574
_exptl_absorpt_coefficient_mu    0.112
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_preparation       nil
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate.hexane'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.051
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1875
_reflns_number_total             2101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra05082k4.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '399-401' was changed to '400.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_formula_sum        'C12 H12 B1 N1 O5'
_cod_database_code               7220190
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
_shelx_res_checksum              98819
_shelx_hkl_checksum              20465