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_7123564
_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 H19 N O3'
_chemical_formula_sum            'C29 H19 N O3'
_chemical_formula_weight         429.45
_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             2018-04-26
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
;
2019-02-26 deposited with the CCDC.    2019-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.808(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1052(7)
_cell_length_b                   11.9832(7)
_cell_length_c                   13.6414(8)
_cell_measurement_reflns_used    4541
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.4850
_cell_measurement_theta_min      4.3610
_cell_volume                     2117.0(2)
_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
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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)
;
_computing_data_reduction
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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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.981
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

  2 omega   23.00   90.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  150.0000 67

  3 omega    1.00   75.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  120.0000 74

  4 omega   23.00   90.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  -30.0000 67

  5 omega  -31.00   53.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -180.0000 84

  6 omega   23.00   90.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000   30.0000 67

  7 omega   39.00  109.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

  8 omega   38.00   91.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

  9 omega   90.00  175.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 10 omega   87.00  178.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 91

 11 omega   40.00   98.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 12 omega   40.00   98.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 13 omega   40.00   98.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 14 omega   39.00  109.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 15 omega   38.00   91.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 16 omega  100.00  178.00   1.0000   15.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

 17 omega   10.00  104.00   1.0000    3.8100
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -150.0000 94
;
_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      -0.0761604000
_diffrn_orient_matrix_UB_12      0.0619770000
_diffrn_orient_matrix_UB_13      0.0565832000
_diffrn_orient_matrix_UB_21      -0.0829967000
_diffrn_orient_matrix_UB_22      -0.0894674000
_diffrn_orient_matrix_UB_23      -0.0328664000
_diffrn_orient_matrix_UB_31      0.0387135000
_diffrn_orient_matrix_UB_32      -0.0683116000
_diffrn_orient_matrix_UB_33      0.0935093000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11834
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.832
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0532
_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^)+(0.1014P)^2^+0.2084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3478
_reflns_number_total             4137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03400e2.cif
_cod_data_source_block           lj-o-5
_cod_database_code               7123564
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.87
_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), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X)
2.b Idealised Me refined as rotating group:
 C00W(H00A,H00C,H00D)
;
_olex2_submission_special_instructions 'No special instructions were received'