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_7134221
_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         'C28 H23 N O5, 1.3[CH2Cl2]'
_chemical_formula_sum            'C28 H23 N O5'
_chemical_formula_weight         453.47
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2025-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                75.0600(10)
_cell_angle_beta                 81.1420(10)
_cell_angle_gamma                75.9140(10)
_cell_formula_units_Z            4
_cell_length_a                   11.9433(10)
_cell_length_b                   12.3276(10)
_cell_length_c                   20.1320(17)
_cell_measurement_reflns_used    6976
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.21
_cell_volume                     2764.6(4)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1373
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27603
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.104
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  25.68
_exptl_absorpt_correction_T_min  2.21
_exptl_absorpt_correction_type   multi-scan
_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    1.090
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         9696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1414P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2243
_refine_ls_wR_factor_ref         0.2479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6090
_reflns_number_total             9696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06690a2.cif
_cod_data_source_block           220318b_0m
_cod_depositor_comments
'Adding full bibliography for 7134221--7134226.cif.'
_cod_database_code               7134221
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C35(H35), C14(H14), C50(H50)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C36(H36a,H36b), C2(H2a,H2b), C42(H42a,H42b)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C52(H52), C55(H55), C17(H17), C19(H19), C18(H18), C24(H24),
 C32(H32), C34(H34), C53(H53), C54(H54), C28(H28), C49(H49), C45(H45), C29(H29),
  C25(H25), C13(H13), C30(H30), C9(H9), C26(H26), C27(H27), C31(H31), C46(H46),
 C47(H47), C11(H11), C48(H48), C12(H12), C10(H10)
2.d Idealised Me refined as rotating group:
 C43(H43a,H43b,H43c), C1(H1a,H1b,H1c)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 236 electrons were 
found in a volume of 715\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1.3[CH2Cl2] per Asymmetric Unit 
which account for 84 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              17637
_shelx_hkl_checksum              59643
_shelx_fab_checksum              83772
_olex2_submission_special_instructions 'No special instructions were received'