Redox-Neutral Photocatalytic Radical Cascade Cyclization for the Synthesis of CH<sub>2</sub>CN/CF<sub>2</sub>COOEt/CF<sub>3</sub>-Containing Benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-One Derivatives.
Liu, Liang; Yang, De-Yong; He, Yan-Hong; Guan, Zhi; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01688

data_4038728
_publ_section_title
;
 Redox-Neutral Photocatalytic Radical Cascade Cyclization for the
 Synthesis of
 CH<sub>2</sub>CN/CF<sub>2</sub>COOEt/CF<sub>3</sub>-Containing
 Benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-One Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01688
_journal_year                    2020
_chemical_formula_moiety         'C21 H18 F2 N2 O3'
_chemical_formula_sum            'C21 H20 F0.25 N O6'
_chemical_formula_weight         387.13
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.7154(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8490(2)
_cell_length_b                   11.07235(14)
_cell_length_c                   13.3470(2)
_cell_measurement_reflns_used    5846
_cell_measurement_temperature    292(1)
_cell_measurement_theta_max      71.6400
_cell_measurement_theta_min      3.9940
_cell_volume                     1844.71(5)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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    -53.00  31.00   1.00    1.00    --  -35.97  57.00-180.00   84
  2  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
  3  \w     24.00  90.00   1.00    1.00    --   35.97-126.00-150.00   66
  4  \w    -31.00  53.00   1.00    1.00    --   35.97 -57.00-120.00   84
  5  \w     24.00  90.00   1.00    1.00    --   35.97-126.00  90.00   66
  6  \w     24.00  90.00   1.00    1.00    --   35.97-126.00 -30.00   66
  7  \w     40.00 135.00   1.00    1.75    --  107.97 -77.00 -30.00   95
  8  \w     41.00 126.00   1.00    1.75    --  107.97 -61.00  90.00   85
  9  \w     81.00 176.00   1.00    1.75    --  107.97  77.00  90.00   95
 10  \w     87.00 178.00   1.00    1.75    --  107.97  30.00   0.00   91
 11  \w     38.00 112.00   1.00    1.75    --  107.97-112.00 -60.00   74
 12  \w     40.00 125.00   1.00    1.75    --  107.97 -45.00 -60.00   85
 13  \w     39.00 110.00   1.00    1.75    --  107.97 -95.00  60.00   71
 14  \w     57.00 150.00   1.00    1.75    --  107.97 178.00 -30.00   93
 15  \w   -104.00 -20.00   1.00    1.00    --  -35.97 -77.00 -30.00   84
 16  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00-150.00   84
;
_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      -0.0492946000
_diffrn_orient_matrix_UB_12      -0.1157461000
_diffrn_orient_matrix_UB_13      0.0332588000
_diffrn_orient_matrix_UB_21      0.1017419000
_diffrn_orient_matrix_UB_22      -0.0197251000
_diffrn_orient_matrix_UB_23      0.0865145000
_diffrn_orient_matrix_UB_31      -0.0495474000
_diffrn_orient_matrix_UB_32      0.0746643000
_diffrn_orient_matrix_UB_33      0.0743061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10572
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.741
_diffrn_reflns_theta_min         3.541
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80683
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             813
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0585P)^2^+0.1806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3099
_reflns_number_total             3563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01688_si_002.cif
_cod_data_source_block           gz190525
_cod_original_cell_volume        1844.72(5)
_cod_database_code               4038728
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3AA-F1
 1.45 with sigma of 0.02
 C3AA-F6A
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F1A: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008
F6A \\sim F6: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008
4. Others
 Sof(F6A)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(F6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C4AA(H4AA)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2019-05-25
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.833