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_7132784
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-25
_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                90
_cell_angle_beta                 102.790(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1690(2)
_cell_length_b                   10.8560(2)
_cell_length_c                   12.0502(3)
_cell_measurement_reflns_used    3381
_cell_measurement_temperature    170.00(18)
_cell_measurement_theta_max      73.4180
_cell_measurement_theta_min      3.9880
_cell_volume                     1297.27(5)
_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(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_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    -65.00  31.00   1.00    1.00    --  -40.92  37.00  30.00   96
  2  \w     50.00  80.00   1.00    1.00    --   40.92 -99.00 120.00   30
  3  \w     42.00 107.00   1.00    1.00    --  107.58 -45.00 150.00   65
  4  \w     89.00 144.00   1.00    1.00    --  107.58  30.00   0.00   55
  5  \w     96.00 122.00   1.00    1.00    --  107.58  30.00-120.00   26
  6  \w    130.00 176.00   1.00    1.00    --  107.58  30.00-120.00   46
  7  \w     48.00 106.00   1.00    1.00    --  107.58 -94.00 -30.00   58
  8  \w     34.00  76.00   1.00    1.00    --  107.58 -30.00-120.00   42
  9  \w     35.00 136.00   1.00    1.00    --  107.58 -61.00 -30.00  101
 10  \w    -95.00 -69.00   1.00    1.00    --  -40.92-140.00 122.00   26
 11  \w   -100.00 -20.00   1.00    1.00    --  -40.92 -37.00  30.00   80
;
_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      0.0981363000
_diffrn_orient_matrix_UB_12      0.0191017000
_diffrn_orient_matrix_UB_13      0.1158875000
_diffrn_orient_matrix_UB_21      0.1155943000
_diffrn_orient_matrix_UB_22      0.0241182000
_diffrn_orient_matrix_UB_23      -0.0610226000
_diffrn_orient_matrix_UB_31      -0.0335840000
_diffrn_orient_matrix_UB_32      0.1385792000
_diffrn_orient_matrix_UB_33      -0.0054613000
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4569
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.710
_diffrn_reflns_theta_min         5.160
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65603
_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    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0193(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0539P)^2^+0.3043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2282
_reflns_number_total             2541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05082c2.cif
_cod_data_source_block           wx-02-r21-1-2f
_cod_database_code               7132784
_shelx_shelxl_version_number     2018/3
_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:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              34715
_shelx_hkl_checksum              55803
_olex2_date_sample_data_collection 2023-05-25
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.734