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_7123563
_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         'C28 H19 N O'
_chemical_formula_sum            'C28 H19 N O'
_chemical_formula_weight         385.44
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-01 deposited with the CCDC.    2019-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.897(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0456(8)
_cell_length_b                   8.3661(4)
_cell_length_c                   19.3519(10)
_cell_measurement_reflns_used    3349
_cell_measurement_temperature    295.50(11)
_cell_measurement_theta_max      71.3720
_cell_measurement_theta_min      4.8300
_cell_volume                     1998.2(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.50(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_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   -105.00  34.00   1.00    1.00    --  -35.54   0.00  60.00  139
  2  \w   -103.00 -19.00   1.00    1.00    --  -35.54 -57.00-150.00   84
  3  \w     23.00  89.00   1.00    1.00    --   35.54-125.00 -30.00   66
  4  \w     23.00  89.00   1.00    1.00    --   35.54-125.00-150.00   66
  5  \w     89.00 175.00   1.00    1.00    --  106.21  45.00   0.00   86
  6  \w     37.00 109.00   1.00    1.00    --  106.21 -94.00  60.00   72
  7  \w     38.00 124.00   1.00    1.00    --  106.21 -45.00-180.00   86
  8  \w     57.00 150.00   1.00    1.00    --  106.21 178.00   0.00   93
  9  \w     57.00 150.00   1.00    1.00    --  106.21 178.00  60.00   93
 10  \w     68.00 177.00   1.00    1.00    --  106.21  15.00 -60.00  109
 11  \w     39.00 124.00   1.00    1.00    --  106.21 -61.00  90.00   85
 12  \w   -103.00  -9.00   1.00    1.00    --  -35.54 -77.00 -30.00   94
 13  \w    -62.00  32.00   1.00    1.00    --  -35.54  77.00  90.00   94
 14  \w   -103.00  -9.00   1.00    1.00    --  -35.54 -77.00  60.00   94
 15  \w     89.00 144.00   1.00    1.00    --  106.21  45.00-180.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, 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      0.0804005000
_diffrn_orient_matrix_UB_12      0.0088103000
_diffrn_orient_matrix_UB_13      -0.0432241000
_diffrn_orient_matrix_UB_21      -0.0920712000
_diffrn_orient_matrix_UB_22      0.0555655000
_diffrn_orient_matrix_UB_23      -0.0681666000
_diffrn_orient_matrix_UB_31      0.0251831000
_diffrn_orient_matrix_UB_32      0.1753991000
_diffrn_orient_matrix_UB_33      0.0236875000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.473
_diffrn_reflns_theta_min         4.831
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46682
_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    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0797
_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^)+(0.1481P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2040
_refine_ls_wR_factor_ref         0.2282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2888
_reflns_number_total             3811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03400e2.cif
_cod_data_source_block           yjs-lj-3e
_cod_original_cell_volume        1998.3(2)
_cod_database_code               7123563
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00U(H00A,H00F,H00G)
;
_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 2.572
_oxdiff_exptl_absorpt_empirical_full_min 0.549