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_7123566
_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         'C23 H17 N O'
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-01
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-02-26 deposited with the CCDC.    2019-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.9223(4)
_cell_length_b                   15.5634(7)
_cell_length_c                   41.9514(18)
_cell_measurement_reflns_used    2874
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.1240
_cell_measurement_theta_min      6.0420
_cell_volume                     3213.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega   10.00  104.00   1.0000    3.3600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

  2 omega  -31.00   63.00   1.0000    3.3600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -60.0000 94

  3 omega  -31.00   53.00   1.0000    3.3600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

  4 omega  -31.00   63.00   1.0000    3.3600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  5 omega   20.00  104.00   1.0000    3.3600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

  6 omega   87.00  178.00   1.0000   13.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

  7 omega   38.00   91.00   1.0000   13.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

  8 omega   49.00   80.00   1.0000   13.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 31

  9 omega  103.00  177.00   1.0000   13.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 74

 10 omega   61.00  103.00   1.0000   13.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 42
;
_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_UB_11      0.0043699000
_diffrn_orient_matrix_UB_12      0.0207520000
_diffrn_orient_matrix_UB_13      -0.0359022000
_diffrn_orient_matrix_UB_21      -0.0227978000
_diffrn_orient_matrix_UB_22      -0.0965893000
_diffrn_orient_matrix_UB_23      -0.0077027000
_diffrn_orient_matrix_UB_31      -0.3119192000
_diffrn_orient_matrix_UB_32      0.0072244000
_diffrn_orient_matrix_UB_33      0.0000417000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.507
_diffrn_reflns_theta_min         5.686
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0603
_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^)+(0.1056P)^2^+1.0018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1742
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2647
_reflns_number_total             3100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03400e2.cif
_cod_data_source_block           lj-o-18-150k
_cod_database_code               7123566
_reflns_odcompleteness_completeness 99.74
_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(C7A)=Sof(H7A)=1-FVAR(1)
 Sof(C7)=Sof(H7)=FVAR(1)
 Sof(H00F)=Sof(C5A)=Sof(H5A)=1-FVAR(2)
 Sof(H00K)=Sof(C5)=Sof(H5)=FVAR(2)
 Sof(C2A)=Sof(H2A)=1-FVAR(3)
 Sof(C2)=Sof(H2)=FVAR(3)
 Sof(C6A)=Sof(H6A)=1-FVAR(4)
 Sof(C6)=Sof(H6)=FVAR(4)
3.a Secondary CH2 refined with riding coordinates:
 C00J(H00B,H00D)
3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00K(H00K), C00K(H00F), C2(H2), C5(H5), C6(H6), C7(H7), C7A(H7A),
 C5A(H5A), C2A(H2A), C6A(H6A)
3.c Idealised Me refined as rotating group:
 C00L(H00J,H00L,H00M)
;
_shelx_res_checksum              10241
_shelx_hkl_checksum              55319
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-11-01
_olex2_submission_special_instructions 'No special instructions were received'