Synthesis of 1,4-epoxy-2-aryltetrahydro-1-benzazepines <i>via</i> rhodium(III)-catalyzed C-H allylation/intramolecular 1,3-dipolar cycloaddition.
Wang, Xuan; Li, Jianlong; Du, Haifang; Liang, Weihong; Luo, Cheng; Wu, Yunshan; Liu, Bo; Chemical communications (Cambridge, England) 60 (2024) 2401–2404; doi:10.1039/d3cc05082c

data_7132785
_publ_section_title
;
 Synthesis of 1,4-epoxy-2-aryltetrahydro-1-benzazepines <i>via</i>
 rhodium(III)-catalyzed C-H allylation/intramolecular 1,3-dipolar
 cycloaddition.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2401
_journal_page_last               2404
_journal_paper_doi               10.1039/d3cc05082c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C16 H13 F2 N O'
_chemical_formula_sum            'C16 H13 F2 N O'
_chemical_formula_weight         273.27
_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             2023-09-26
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                77.710(3)
_cell_angle_beta                 89.322(3)
_cell_angle_gamma                71.433(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7065(3)
_cell_length_b                   11.7198(4)
_cell_length_c                   12.0290(4)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.7390
_cell_volume                     1265.13(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.00  33.00   1.00    1.00    --  -40.73  38.00 -90.00   93
  2  \w      5.00  34.00   1.00    1.00    --   40.73 -99.00-180.00   29
  3  \w     60.00  90.00   1.00    1.00    --   40.73-125.00 -90.00   30
  4  \w     90.00 116.00   1.00    1.00    --  106.95-125.00 -30.00   26
  5  \w     94.00 133.00   1.00    1.00    --  106.95 -45.00  90.00   39
  6  \w     89.00 172.00   1.00    1.00    --  106.95  30.00  90.00   83
  7  \w    127.00 173.00   1.00    1.00    --  106.95  61.00  30.00   46
  8  \w     95.00 122.00   1.00    1.00    --  106.95 125.00 -30.00   27
  9  \w     78.00 123.00   1.00    1.00    --  106.95  61.00  30.00   45
 10  \w     75.00 132.00   1.00    1.00    --  106.95  77.00 -60.00   57
 11  \w     81.00 171.00   1.00    1.00    --  106.95  45.00 150.00   90
 12  \w     41.00  67.00   1.00    1.00    --  106.95-125.00 -30.00   26
 13  \w     33.00 138.00   1.00    1.00    --  106.95 -77.00 -30.00  105
 14  \w     36.00 105.00   1.00    1.00    --  106.95 -77.00-120.00   69
 15  \w     27.00 102.00   1.00    1.00    --  106.95 -94.00-180.00   75
 16  \w     34.00 121.00   1.00    1.00    --  106.95-125.00 150.00   87
 17  \w    -69.00  25.00   1.00    1.00    --  -40.73  57.00 120.00   94
 18  \w   -113.00 -22.00   1.00    1.00    --  -40.73 -57.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1232963000
_diffrn_orient_matrix_UB_12      0.0068301000
_diffrn_orient_matrix_UB_13      -0.0831916000
_diffrn_orient_matrix_UB_21      -0.1130510000
_diffrn_orient_matrix_UB_22      0.0740049000
_diffrn_orient_matrix_UB_23      0.0710191000
_diffrn_orient_matrix_UB_31      0.0123592000
_diffrn_orient_matrix_UB_32      0.1211974000
_diffrn_orient_matrix_UB_33      -0.0726565000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8430
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.544
_diffrn_reflns_theta_min         3.768
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0880P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4444
_reflns_number_total             4941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05082c2.cif
_cod_data_source_block           ljl-39-2
_cod_database_code               7132785
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C24(H24), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C23(H23A,H23B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C20(H20),
 C21(H21), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              60713
_shelx_hkl_checksum              9275
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.132
_oxdiff_exptl_absorpt_empirical_full_min 0.392