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_7133926
_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         'C45 H33 N3 O4'
_chemical_formula_sum            'C45 H33 N3 O4'
_chemical_formula_weight         679.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                86.314(2)
_cell_angle_beta                 80.905(2)
_cell_angle_gamma                81.884(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5254(9)
_cell_length_b                   11.8656(11)
_cell_length_c                   17.5066(16)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      27.361
_cell_measurement_theta_min      2.321
_cell_volume                     1932.4(3)
_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      296.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25538
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.140
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3384
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1548 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.4539.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         6696
_refine_ls_number_restraints     432
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1277P)^2^+1.0271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4557
_reflns_number_total             6696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04394d2.cif
_cod_data_source_block           1
_cod_database_code               7133926
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.981
_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
C00L \\sim C01C \\sim C01H \\sim C01D \\sim C015 \\sim C00U \\sim C6 \\sim C7
\\sim C0 \\sim C9 \\sim C01I \\sim C10: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
C01E \\sim C01F \\sim C01G \\sim C00V \\sim C1 \\sim C8 \\sim C2 \\sim C5 \\sim
C4 \\sim C3 \\sim C8A \\sim C1A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C00V, C01E, C01F, C01G, C1, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00U, C015, C01C, C01D, C01H, C00L
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(C2)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(H3)=Sof(C8A)=Sof(H8A)=
 Sof(C1A)=Sof(H1A)=1-FVAR(1)
 Sof(C01E)=Sof(H01G)=Sof(C01F)=Sof(H01I)=Sof(C01G)=Sof(H01J)=Sof(C00V)=Sof(C1)=
 Sof(H1)=Sof(C8)=Sof(H8)=FVAR(1)
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C0)=Sof(H0)=Sof(C9)=Sof(H9)=Sof(C01I)=Sof(H01K)=
 Sof(C10)=Sof(H10)=1-FVAR(2)
 Sof(C00L)=Sof(C01C)=Sof(H01C)=Sof(C01H)=Sof(H01H)=Sof(C01D)=Sof(H01D)=
 Sof(C015)=Sof(H015)=Sof(C00U)=Sof(H00U)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C)
5.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C01C(H01C), C01H(H01H), C01D(H01D), C015(H015), C00U(H00U),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012), C013(H013), C014(H014),
 C017(H017), C019(H019), C01A(H01A), C01E(H01G), C01F(H01I), C01G(H01J), C1(H1),
  C8(H8), C5(H5), C4(H4), C3(H3), C8A(H8A), C1A(H1A), C7(H7), C0(H0), C9(H9),
 C01I(H01K), C10(H10)
5.c Fitted hexagon refined as free rotating group:
 C00L(C01C,C01H,C01D,C015,C00U), C01E(C01F,C01G,C00V,C1,C8), C2(C5,C4,C3,C8A,
 C1A), C6(C7,C0,C9,C01I,C10)
5.d Idealised Me refined as rotating group:
 C01B(H01B,H01E,H01F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              76632
_shelx_hkl_checksum              83466
_shelx_fab_checksum              98759
_olex2_submission_special_instructions 'No special instructions were received'