Construction of atropisomeric benzoxepinone-embedded styrenes <i>via</i> intramolecular [3+2] cycloaddition and catalytic kinetic resolution.
Wang, Yue; Wei, Xingfu; Xue, Aiqi; Huang, Yue; Qu, Jingping; Wang, Baomin; Chemical communications (Cambridge, England) 60 (2024) 12864–12867; doi:10.1039/d4cc04394d

data_7133927
_publ_section_title
;
 Construction of atropisomeric benzoxepinone-embedded styrenes <i>via</i>
 intramolecular [3+2] cycloaddition and catalytic kinetic resolution.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12864
_journal_page_last               12867
_journal_paper_doi               10.1039/d4cc04394d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C39 H30 N2 O4'
_chemical_formula_sum            'C39 H30 N2 O4'
_chemical_formula_weight         590.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2024-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.818(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0367(14)
_cell_length_b                   15.1484(18)
_cell_length_c                   17.888(2)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    263.0
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.27
_cell_volume                     3507.6(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      263.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48750
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.069
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0944 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8864.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         6146
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0748
_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^)+(0.1504P)^2^+2.0964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2397
_refine_ls_wR_factor_ref         0.2512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4692
_reflns_number_total             6146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04394d2.cif
_cod_data_source_block           1_CCDC1
_cod_database_code               7133927
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C02C \\sim C01X \\sim C01K \\sim C00W \\sim C01C \\sim C02D \\sim C00N \\sim
C015 \\sim C01T \\sim C01Y: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C00I(H00I), C00L(H00L), C00R(H00R)
3.b Aromatic/amide H refined with riding coordinates:
 C00T(H00T), C00Y(H00Y), C01C(H01C), C01D(H01D), C01M(H01M), C01O(H01O),
 C01P(H01P), C01S(H01S), C01T(H01T), C01W(H01W), C01X(H01X), C01Y(H01Y),
 C021(H021), C023(H023), C028(H028), C02C(H02C), C02D(H02D), C02F(H02F),
 C02I(H02I), C02M(H02M)
3.c Idealised Me refined as rotating group:
 C02G(H02A,H02B,H02E), C02Q(H02G,H02H,H02J)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              35212
_shelx_hkl_checksum              55581
_shelx_fab_checksum              5402
_olex2_submission_special_instructions 'No special instructions were received'