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_7134225
_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         'C27 H27 N O3'
_chemical_formula_sum            'C27 H27 N O3'
_chemical_formula_weight         413.49
_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             2023-11-10
_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                85.359(2)
_cell_angle_beta                 80.756(2)
_cell_angle_gamma                85.323(2)
_cell_formula_units_Z            4
_cell_length_a                   10.0943(6)
_cell_length_b                   12.4294(8)
_cell_length_c                   18.1764(13)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.90
_cell_volume                     2238.1(3)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1600
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            80513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.600
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_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    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         7849
_refine_ls_number_restraints     537
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0610P)^2^+0.8506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5425
_reflns_number_total             7849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06690a2.cif
_cod_data_source_block           mo_20231110d_0m
_cod_depositor_comments
'Adding full bibliography for 7134221--7134226.cif.'
_cod_database_code               7134225
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.984
_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 C(H,H,H) groups
2. Restrained distances
 C01Q-C017 \\sim C01R-C0
 with sigma of 0.02
 O1-C017 \\sim O1A-C0
 with sigma of 0.02
 O002-C017 \\sim O002-C0
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(O005) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C017
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O002, C017, C01Q, O1, C0, C01R, O1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C0)=Sof(C01R)=Sof(H01m)=Sof(H01n)=Sof(H01o)=Sof(O1A)=1-FVAR(1)
 Sof(C017)=Sof(C01Q)=Sof(H01f)=Sof(H01i)=Sof(H01j)=Sof(O1)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R)
6.b Secondary CH2 refined with riding coordinates:
 C00U(H00b,H00c), C011(H01p,H01q), C013(H01a,H01b), C01D(H01t,H01u), C01F(H01d,
 H01e), C01I(H01w,H01x)
6.c Aromatic/amide H refined with riding coordinates:
 N006(H006), N007(H007), C00E(H00E), C00K(H00K), C00Q(H00Q), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C012(H012), C014(H014), C015(H015), C016(H016), C018(H018), C019(H019),
 C01A(H01c), C01B(H01r), C01C(H01s), C01E(H01v), C01G(H01G), C01H(H01H),
 C01J(H01y), C01K(H01K), C01L(H01L), C01M(H01z), C01N(H01), C01O(H1)
6.d Idealised Me refined as rotating group:
 C01P(H2,H,Ha), C01Q(H01f,H01i,H01j), C01R(H01m,H01n,H01o)
;
_shelx_res_checksum              43984
_shelx_hkl_checksum              81436
_olex2_submission_special_instructions 'No special instructions were received'