Diastereoselective synthesis of benzazocines by Zn(OTf)<sub>2</sub>-catalyzed (4+4) cyclocondensation of multisubstituted donor-acceptor cyclopropanes with anthranils.
Huang, Xuelian; Yang, Gaosheng; Chai, Zhuo; Chemical communications (Cambridge, England) 61 (2025) 3704–3707; doi:10.1039/d4cc06690a

data_7134226
_publ_section_title
;
 Diastereoselective synthesis of benzazocines by
 Zn(OTf)<sub>2</sub>-catalyzed (4+4) cyclocondensation of multisubstituted
 donor-acceptor cyclopropanes with anthranils.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3704
_journal_page_last               3707
_journal_paper_doi               10.1039/d4cc06690a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '0.061(C28 H25 N O4)'
_chemical_formula_sum            'C1.697 H1.515 N0.061 O0.242'
_chemical_formula_weight         26.637
_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_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2025-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.664(5)
_cell_angle_beta                 97.936(5)
_cell_angle_gamma                110.262(4)
_cell_formula_units_Z            33
_cell_length_a                   9.838(4)
_cell_length_b                   11.101(4)
_cell_length_c                   11.425(4)
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.25
_cell_volume                     1137.1(7)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9913
_diffrn_measured_fraction_theta_max 0.9546
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.9913
_diffrn_reflns_Laue_measured_fraction_max 0.9546
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9787
_diffrn_reflns_point_group_measured_fraction_full 0.9913
_diffrn_reflns_point_group_measured_fraction_max 0.9546
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.83
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8468.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             464.299
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.2834
_refine_diff_density_min         -0.3145
_refine_diff_density_rms         0.0632
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             11.0983
_refine_ls_goodness_of_fit_ref   1.0833
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0833
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.0269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3074
_reflns_number_total             4981
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc06690a2.cif
_cod_data_source_block           230322b_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134221--7134226.cif.'
_cod_original_cell_volume        1137.0(7)
_cod_database_code               7134226
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C27(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C14(H14), C21(H21), C3(H3), C4(H4), C18(H18), C15(H15),
 C25(H25), C17(H17), C16(H16), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c)
;
_olex2_submission_special_instructions 'No special instructions were received'