Photoinduced Synthesis of Fluorinated Dibenz[b,e]azepines via Radical Triggered Cyclization
Zhong, Jian-Ji; Qi, Xu-Kuan; Zhang, Hong; Pan, Zi-Tong; Liang, Rong-Bin; Zhu, Can-Ming; Li, Jing-Hong; Tong, Qing-Xiao; Gao, Xue-Wang; Wu, Li-Zhu; Chemical Communications  (2019) –; doi:10.1039/C9CC04977K

data_7123976
_publ_section_title
;
 Photoinduced Synthesis of Fluorinated Dibenz[b,e]azepines via Radical
 Triggered Cyclization
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04977K
_journal_year                    2019
_chemical_formula_moiety         'C18 H11 F6 N O'
_chemical_formula_sum            'C18 H11 F6 N O'
_chemical_formula_weight         371.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-27 deposited with the CCDC.    2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.227(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8518(2)
_cell_length_b                   15.2537(5)
_cell_length_c                   26.0789(7)
_cell_measurement_reflns_used    10957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0310
_cell_measurement_theta_min      3.3450
_cell_volume                     3121.08(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_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     -8.00  67.00   0.50    0.58    --    0.00  38.00  30.00  150
  2  \w     -7.00  20.00   0.50    0.58    --    0.00 -57.00 -30.00   54
  3  \w    -53.00 -11.00   0.50    0.58    --    0.00 -57.00 -30.00   84
  4  \w    -88.00 -58.00   0.50    0.58    --    0.00 -57.00 -30.00   60
  5  \w    -39.00  -2.00   0.50    0.58    --    0.00 -77.00-180.00   74
  6  \w     34.00 121.00   0.50    3.50    --   95.80 -82.00-150.00  174
  7  \w     55.00 111.00   0.50    3.50    --   95.80 -61.00 -60.00  112
  8  \w     77.00 104.00   0.50    3.50    --   95.80 -82.00-180.00   54
  9  \w      6.00  45.00   0.50    3.50    --   95.80 -61.00 -60.00   78
 10  \w     56.00 114.00   0.50    3.50    --   95.80 -61.00  30.00  116
 11  \w     21.00 122.00   0.50    3.50    --   95.80 -82.00 120.00  202
 12  \w      8.00  35.00   0.50    3.50    --   95.80 -61.00  30.00   54
 13  \w     79.00 104.00   0.50    3.50    --   95.80 -82.00-120.00   50
 14  \w     84.00 110.00   0.50    3.50    --   95.80  30.00-180.00   52
 15  \w     82.00 185.00   0.50    3.50    --   95.80  30.00  60.00  206
 16  \w      7.00  36.00   0.50    3.50    --   95.80 -82.00-180.00   58
 17  \w     77.00 183.00   0.50    3.50    --   95.80  45.00 -30.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0272456000
_diffrn_orient_matrix_UB_12      -0.0715659000
_diffrn_orient_matrix_UB_13      0.0410080000
_diffrn_orient_matrix_UB_21      -0.0305365000
_diffrn_orient_matrix_UB_22      -0.0712558000
_diffrn_orient_matrix_UB_23      -0.0413499000
_diffrn_orient_matrix_UB_31      0.1920820000
_diffrn_orient_matrix_UB_32      -0.0013126000
_diffrn_orient_matrix_UB_33      -0.0100853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18741
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.300
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         6153
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0588P)^2^+2.5452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5346
_reflns_number_total             6153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04977k2.cif
_cod_data_source_block           181012c
_cod_original_cell_volume        3121.07(16)
_cod_database_code               7123976
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O F'
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F12'-C30
 1.38 with sigma of 0.02
 F10'-C30
 1.38 with sigma of 0.02
 F1'-C14
 1.38 with sigma of 0.02
3. Others
 Fixed Sof: F1(0.8) F1'(0.2) F2(0.4) F2'(0.6) F3(0.5) F3'(0.5) F4(0.5)
 F4'(0.5) F5(0.5) F5'(0.5) F6(0.5) F6'(0.5) F10(0.5) F10'(0.5) F11(0.5)
 F11'(0.5) F12(0.5) F12'(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C28(H28a,H28b)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C23(H23), C24(H24), C25(H25), C26(H26), C33(H33), C34(H34), C35(H35), C36(H36)
;
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.649