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_7134223
_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         'C25 H25 N O2'
_chemical_formula_sum            'C25 H25 N O2'
_chemical_formula_weight         371.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2025-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3577(14)
_cell_length_b                   12.6655(16)
_cell_length_c                   27.035(3)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.474
_cell_measurement_theta_min      2.409
_cell_volume                     3889.0(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32590
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         1.506
_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    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1037 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8542. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2692 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8633
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0850P)^2^+0.1484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                6902
_reflns_number_total             8633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06690a2.cif
_cod_data_source_block           230510c_0m
_cod_depositor_comments
'Adding full bibliography for 7134221--7134226.cif.'
_cod_database_code               7134223
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N0AA(H0AA), N3(H3B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C28(H28), C7(H7), C26(H26), C19(H19), C43(H43)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C35(H35A,H35B), C27(H27A,H27B), C10(H10A,H10B), C12(H12A,H12B),
 C36(H36A,H36B)
2.d Aromatic/amide H refined with riding coordinates:
 C49(H49), C48(H48), C24(H24), C18(H18), C38(H38), C2(H2), C47(H47), C30(H30),
 C39(H39), C6(H6), C17(H17), C40(H40), C42(H42), C46(H46), C34(H34), C31(H31),
 C3(H3), C14(H14), C23(H23), C5(H5), C21(H21), C33(H33), C4(H4), C16(H16),
 C22(H22), C32(H32), C15(H15), C41(H41)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_shelx_res_checksum              49084
_shelx_hkl_checksum              40843
_olex2_submission_special_instructions 'No special instructions were received'