A formal (5+1) annulation reaction from heterodimerization of two different isocyanides: stereoselective synthesis of 2H-benzo[b][1,4]oxazin-2-one
Li, Jian; Su, Shikuan; Hu, Jie; Cui, Yongmei; Tang, Chongrong; Chen, Yali; Chemical Communications  (2019) –; doi:10.1039/C9CC06678K

data_7124204
_publ_section_title
;
 A formal (5+1) annulation reaction from heterodimerization of two
 different isocyanides: stereoselective synthesis of
 2H-benzo[b][1,4]oxazin-2-one
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06678K
_journal_year                    2019
_chemical_formula_sum            'C20 H17 Br N2 O4'
_chemical_formula_weight         429.26
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-01 deposited with the CCDC.    2019-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                94.6090(10)
_cell_angle_beta                 105.3440(10)
_cell_angle_gamma                96.0880(10)
_cell_formula_units_Z            4
_cell_length_a                   10.4647(3)
_cell_length_b                   13.4623(4)
_cell_length_c                   14.0577(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      57.01
_cell_measurement_theta_min      3.83
_cell_volume                     1886.89(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25232
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.100
_diffrn_reflns_theta_min         2.890
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         7729
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0375P)^2^+0.9326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6705
_reflns_number_total             7729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06678k2.cif
_cod_data_source_block           ga_80607b_1_a
_cod_database_code               7124204
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.620
_shelx_estimated_absorpt_t_max   0.702
_shelx_res_checksum              22924