Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives
Wang, Zhe-Hao; Zhang, Huan-Huan; Wang, Dao-Ming; Xu, Peng-Fei; Luo, Yong-Chun; Chem. Commun.  (2017) –; doi:10.1039/C7CC04239F

data_7120451
_publ_section_title
;
 Lewis acid catalyzed diastereoselective [3+4]-annulation of
 donor--acceptor cyclopropanes with anthranils: synthesis of
 tetrahydro-1-benzazepine derivatives
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04239F
_journal_year                    2017
_chemical_formula_moiety         'C23 H25 N O5'
_chemical_formula_sum            'C23 H25 N O5'
_chemical_formula_weight         395.44
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-28 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                78.762(7)
_cell_angle_beta                 85.450(6)
_cell_angle_gamma                89.969(6)
_cell_formula_units_Z            4
_cell_length_a                   11.8383(9)
_cell_length_b                   13.1551(10)
_cell_length_c                   13.6364(10)
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      26.2060
_cell_measurement_theta_min      3.7940
_cell_volume                     2076.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -90.00  -22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -57.0000 -120.0000 68

  2 omega   -4.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -120.0000 28

  3 omega   -5.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000 -180.0000 70

  4 omega  -48.00   -8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 40

  5 omega   -1.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  120.0000 93

  6 omega  -48.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -30.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0251664000
_diffrn_orient_matrix_UB_12      -0.0424630000
_diffrn_orient_matrix_UB_13      -0.0180434000
_diffrn_orient_matrix_UB_21      0.0383287000
_diffrn_orient_matrix_UB_22      0.0345246000
_diffrn_orient_matrix_UB_23      -0.0330316000
_diffrn_orient_matrix_UB_31      0.0388720000
_diffrn_orient_matrix_UB_32      -0.0052530000
_diffrn_orient_matrix_UB_33      0.0376059000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13599
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         8179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.6252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                5444
_reflns_number_total             8179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04239f3.cif
_cod_data_source_block           luoych_0627
_cod_database_code               7120451
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7), C10(H10), C30(H30), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C25(H25), C26(H26), C27(H27), C28(H28), C35(H35), C36(H36), C37(H37),
  C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C41(H41A,H41B,H41C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C46(H46A,
 H46B,H46C)
;
_olex2_date_sample_data_collection 2017-06-27
_olex2_submission_special_instructions 'No special instructions were received'