Two birds with one stone: one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent
Gao, Cai; Li, Bin; Geng, Xueyang; Zhou, Qianting; Zhang, Xinying; Fan, Xuesen; Green Chemistry 21 (2019) 5113–; doi:10.1039/C9GC02001B

data_7233403
_publ_section_title
;
 Two birds with one stone: one-pot simultaneous synthesis of
 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the
 utilization of the byproduct of Togni's reagent
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              5113
_journal_paper_doi               10.1039/C9GC02001B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C19 H14 F3 N O'
_chemical_formula_sum            'C19 H14 F3 N O'
_chemical_formula_weight         329.31
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-17
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-15 deposited with the CCDC.    2019-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.404(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5181(2)
_cell_length_b                   21.4287(4)
_cell_length_c                   7.5942(2)
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      71.0840
_cell_measurement_theta_min      4.1130
_cell_volume                     1442.09(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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   -103.00 -19.00   1.00    1.23    --  -35.37 -57.00 -60.00   84
  2  \w    -32.00  62.00   1.00    1.23    --   35.37 -77.00 -60.00   94
  3  \w      6.00 107.00   1.00    1.23    --   35.37  19.00 -90.00  101
  4  \w     19.00 103.00   1.00    1.23    --   35.37  57.00 -90.00   84
  5  \w      1.00  74.00   1.00    1.23    --   35.37 -99.00 150.00   73
  6  \w     88.00 173.00   1.00    4.91    --  106.50  61.00-180.00   85
  7  \w     57.00 151.00   1.00    4.91    --  106.50 178.00  90.00   94
  8  \w     88.00 173.00   1.00    4.91    --  106.50  61.00-150.00   85
  9  \w     37.00 112.00   1.00    4.91    --  106.50-111.00 -60.00   75
 10  \w     88.00 173.00   1.00    4.91    --  106.50  61.00-120.00   85
 11  \w     37.00 109.00   1.00    4.91    --  106.50 -95.00-180.00   72
 12  \w    100.00 176.00   1.00    4.91    --  106.50 111.00  90.00   76
 13  \w     37.00 109.00   1.00    4.91    --  106.50 -95.00 -60.00   72
 14  \w     40.00 125.00   1.00    4.91    --  106.50 -61.00  60.00   85
 15  \w      9.00  92.00   1.00    1.23    --   35.37  77.00  60.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1733789000
_diffrn_orient_matrix_UB_12      0.0000312000
_diffrn_orient_matrix_UB_13      -0.0941921000
_diffrn_orient_matrix_UB_21      -0.0001112000
_diffrn_orient_matrix_UB_22      0.0719030000
_diffrn_orient_matrix_UB_23      0.0043508000
_diffrn_orient_matrix_UB_31      0.0127731000
_diffrn_orient_matrix_UB_32      0.0015868000
_diffrn_orient_matrix_UB_33      -0.1963398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.248
_diffrn_reflns_theta_min         4.126
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0527
_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^+1.8912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             2760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02001b2.cif
_cod_data_source_block           4j
_cod_depositor_comments          'Adding full bibliography for 7233403.cif.'
_cod_database_code               7233403
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.822
_reflns_odcompleteness_completeness 99.92
_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.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C18(H18A,H18B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C7(H7), C9(H9), C10(H10), C8(H8)
;
_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 1.598
_oxdiff_exptl_absorpt_empirical_full_min 0.265