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_7123565
_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 H15 Br2 N O'
_chemical_formula_sum            'C28 H15 Br2 N O'
_chemical_formula_weight         541.23
_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             2018-11-20
_audit_creation_method
;
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                   9.3487(4)
_cell_length_b                   14.9382(7)
_cell_length_c                   31.3522(11)
_cell_measurement_reflns_used    4598
_cell_measurement_temperature    293.27(13)
_cell_measurement_theta_max      72.5280
_cell_measurement_theta_min      5.1050
_cell_volume                     4378.4(3)
_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      293.27(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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    -55.00  33.00   1.00    1.10    --  -36.04  38.00 150.00   88
  2  \w   -103.00 -19.00   1.00    1.10    --  -36.04 -57.00-150.00   84
  3  \w     17.00 105.00   1.00    1.10    --   36.04  38.00  30.00   88
  4  \w     23.00  89.00   1.00    1.10    --   36.04-125.00-150.00   66
  5  \w    100.00 178.00   1.00    4.41    --  108.71 111.00 150.00   78
  6  \w     87.00 178.00   1.00    4.41    --  108.71  30.00 -30.00   91
  7  \w     39.00 109.00   1.00    4.41    --  108.71 -94.00 120.00   70
  8  \w     47.00 112.00   1.00    4.41    --  108.71 -61.00 150.00   65
  9  \w     79.00 129.00   1.00    4.41    --  108.71 -30.00 -30.00   50
;
_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      0.0212075000
_diffrn_orient_matrix_UB_12      -0.0341288000
_diffrn_orient_matrix_UB_13      0.0459354000
_diffrn_orient_matrix_UB_21      0.0031478000
_diffrn_orient_matrix_UB_22      0.0972993000
_diffrn_orient_matrix_UB_23      0.0162907000
_diffrn_orient_matrix_UB_31      -0.1633503000
_diffrn_orient_matrix_UB_32      -0.0024970000
_diffrn_orient_matrix_UB_33      0.0062878000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12509
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.878
_diffrn_reflns_theta_min         5.510
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05415
_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 greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_description       plate
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0746
_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^)+(0.1404P)^2^+3.7064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3408
_reflns_number_total             4295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03400e2.cif
_cod_data_source_block           lj-c-3
_cod_database_code               7123565
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W)
;
_shelx_res_checksum              6086
_shelx_hkl_checksum              26602
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-11-20
_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 9.771
_oxdiff_exptl_absorpt_empirical_full_min 0.444