Cascade intramolecular imidoylation and C−H activation/annulat-ion of benzimidoyl chlorides with alkynes: one-pot synthesis of 7H-dibenzo[de,h]quinoline analogues
Liu, Jiao; Fang, Hao; Cheng, Rui; Wang, Zhishuo; Yang, Yudong; You, Jingsong; Chemical Communications  (2019) –; doi:10.1039/C9CC03400E

data_7123561
_publ_section_title
;
 Cascade intramolecular imidoylation and C&#x2212;H activation/annulat-ion
 of benzimidoyl chlorides with alkynes: one-pot synthesis of
 7H-dibenzo[de,h]quinoline analogues
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03400E
_journal_year                    2019
_chemical_formula_moiety         'C29 H21 F N2'
_chemical_formula_sum            'C29 H21 F N2'
_chemical_formula_weight         416.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-26 deposited with the CCDC.    2019-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                80.602(5)
_cell_angle_beta                 83.475(5)
_cell_angle_gamma                88.358(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0309(5)
_cell_length_b                   11.6771(7)
_cell_length_c                   13.3907(7)
_cell_measurement_reflns_used    3306
_cell_measurement_temperature    294.1(6)
_cell_measurement_theta_max      72.3900
_cell_measurement_theta_min      5.4840
_cell_volume                     1077.54(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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_environment      air
_diffrn_ambient_temperature      294.1(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_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   -104.00  -9.00   1.00    1.75    --  -36.04 -77.00 120.00   95
  2  \w    -63.00  32.00   1.00    1.75    --  -36.04  77.00-120.00   95
  3  \w     23.00  89.00   1.00    1.75    --   36.04-125.00  30.00   66
  4  \w     23.00  89.00   1.00    1.75    --   36.04-125.00  90.00   66
  5  \w    -33.00 105.00   1.00    1.75    --   36.04   0.00 -90.00  138
  6  \w     23.00  89.00   1.00    1.75    --   36.04-125.00   0.00   66
  7  \w     39.00 130.00   1.00    7.02    --  108.71 -30.00 -90.00   91
  8  \w     57.00 151.00   1.00    7.02    --  108.71 178.00 -90.00   94
  9  \w     41.00 135.00   1.00    7.02    --  108.71 -77.00 -30.00   94
 10  \w     39.00 109.00   1.00    7.02    --  108.71 -94.00-120.00   70
 11  \w     82.00 176.00   1.00    7.02    --  108.71  77.00  60.00   94
 12  \w     40.00 126.00   1.00    7.02    --  108.71 -45.00  60.00   86
 13  \w     39.00 115.00   1.00    7.02    --  108.71-111.00   0.00   76
 14  \w     91.00 176.00   1.00    7.02    --  108.71  61.00  90.00   85
 15  \w     39.00 109.00   1.00    7.02    --  108.71 -94.00  60.00   70
 16  \w    100.00 178.00   1.00    7.02    --  108.71 111.00 -30.00   78
 17  \w    100.00 178.00   1.00    7.02    --  108.71 111.00  30.00   78
 18  \w     39.00 115.00   1.00    7.02    --  108.71-111.00 150.00   76
 19  \w    100.00 178.00   1.00    7.02    --  108.71 111.00   0.00   78
 20  \w     87.00 178.00   1.00    7.02    --  108.71  30.00 -60.00   91
 21  \w   -104.00  -9.00   1.00    1.75    --  -36.04 -77.00 -90.00   95
 22  \w      9.00 104.00   1.00    1.75    --   36.04  77.00-150.00   95
 23  \w     19.00 103.00   1.00    1.75    --   36.04  57.00  30.00   84
 24  \w      9.00 104.00   1.00    1.75    --   36.04  77.00  60.00   95
 25  \w     17.00 105.00   1.00    1.75    --   36.04  38.00 -30.00   88
 26  \w    -31.00  53.00   1.00    1.75    --   36.04 -57.00 120.00   84
 27  \w     70.00 145.00   1.00    7.02    --  108.71  15.00-150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0416451000
_diffrn_orient_matrix_UB_12      -0.1263885000
_diffrn_orient_matrix_UB_13      0.0469621000
_diffrn_orient_matrix_UB_21      0.0872480000
_diffrn_orient_matrix_UB_22      -0.0248477000
_diffrn_orient_matrix_UB_23      -0.1052414000
_diffrn_orient_matrix_UB_31      0.1982372000
_diffrn_orient_matrix_UB_32      0.0359536000
_diffrn_orient_matrix_UB_33      0.0220293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10775
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.602
_diffrn_reflns_theta_min         3.837
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0765
_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^)+(0.1616P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2808
_reflns_number_total             4187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03400e2.cif
_cod_data_source_block           lj-6a
_cod_original_cell_volume        1077.54(11)
_cod_database_code               7123561
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.56
_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. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1A(H1AA,H1AB)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC)
;
_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 3.151
_oxdiff_exptl_absorpt_empirical_full_min 0.353