Metal-free and enantioselective synthesis of 1,4-benzoxazepines from <i>para</i>-quinone methide derivatives and α-bromohydroxamates.
Qi, Suo-Suo; Luo, Xin; Sun, Xiao-Ping; Zhai, Jing-Jing; Chu, Ming-Ming; Chen, Jin; Wang, Yi-Feng; Xu, Dan-Qian; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc02368k

data_7131755
_publ_section_title
;
 Metal-free and enantioselective synthesis of 1,4-benzoxazepines from
 <i>para</i>-quinone methide derivatives and &#x3b1;-bromohydroxamates.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc02368k
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C H2 Cl2, C30 H34 F N O4'
_chemical_formula_sum            'C31 H36 Cl2 F N O4'
_chemical_formula_weight         576.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-16 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.13420(10)
_cell_length_b                   10.9767(2)
_cell_length_c                   27.3919(4)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      53.748
_cell_measurement_theta_min      2.808
_cell_volume                     3047.08(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32680
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.997
_diffrn_reflns_theta_min         3.774
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.486
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1097 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.7904.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.123
_refine_diff_density_min         -0.939
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1729 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5782
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0754
_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^)+(0.1339P)^2^+2.3358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2166
_refine_ls_wR_factor_ref         0.2322
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4731
_reflns_number_total             5782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02368k2.cif
_cod_data_source_block           2201033445_0m
_cod_database_code               7131755
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H4-H24C
 2.05 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C8(H8A,H8B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C22(H22)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              97360
_shelx_hkl_checksum              45195
_olex2_submission_special_instructions 'No special instructions were received'