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_7120454
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 Br N O5'
_chemical_formula_sum            'C20 H18 Br N O5'
_chemical_formula_weight         432.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-07-11 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8280(3)
_cell_length_b                   11.7422(5)
_cell_length_c                   23.4879(10)
_cell_measurement_reflns_used    1201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1580
_cell_measurement_theta_min      3.8730
_cell_volume                     1883.16(14)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -8.00   21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000  -60.0000 29

  2 omega   -4.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   38.0000  -30.0000 90

  3 omega    1.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000 -180.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0137857000
_diffrn_orient_matrix_UB_12      0.0336434000
_diffrn_orient_matrix_UB_13      -0.0247529000
_diffrn_orient_matrix_UB_21      0.0132838000
_diffrn_orient_matrix_UB_22      0.0501093000
_diffrn_orient_matrix_UB_23      0.0164175000
_diffrn_orient_matrix_UB_31      0.1021160000
_diffrn_orient_matrix_UB_32      -0.0019642000
_diffrn_orient_matrix_UB_33      -0.0054784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4814
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73588
_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    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 670 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0343P)^2^+0.1800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.565
_reflns_Friedel_fraction_full    0.800
_reflns_Friedel_fraction_max     0.778
_reflns_number_gt                2403
_reflns_number_total             3367
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04239f2.cif
_cod_data_source_block           wangzhh_0228_2
_cod_original_cell_volume        1883.16(13)
_cod_database_code               7120454
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.60
_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)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_olex2_date_sample_data_collection 2017-02-28
_olex2_submission_special_instructions 'No special instructions were received'