Copper Catalyzed Preparation of Benzo[3,4]indolo[1,2-b]isoquinoline-8-ones and Photoluminescence Exploration.
Hua, Yiwen; Chen, Zi-Yan; Diao, Hanying; Zhang, Lianpeng; Qiu, Guanyinsheng; Gao, Xiaoxing; Zhou, Hongwei; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00936

data_4038605
_publ_section_title
;
 Copper Catalyzed Preparation of
 Benzo[3,4]indolo[1,2-b]isoquinoline-8-ones and Photoluminescence
 Exploration.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00936
_journal_year                    2020
_chemical_formula_moiety         'C26 H17 N O'
_chemical_formula_sum            'C26 H17 N O'
_chemical_formula_weight         359.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                85.580(11)
_cell_angle_beta                 72.746(10)
_cell_angle_gamma                67.106(12)
_cell_formula_units_Z            2
_cell_length_a                   9.9459(11)
_cell_length_b                   10.0372(15)
_cell_length_c                   10.2116(12)
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      71.6120
_cell_measurement_theta_min      4.5310
_cell_volume                     896.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.971
_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     35.00 103.00   1.00    2.99    --   36.77  57.00 -90.00   68
  2  \w     18.00 105.00   1.00    2.99    --   36.77  38.00-180.00   87
  3  \w     -4.00  68.00   1.00    2.99    --   36.77 -99.00  90.00   72
  4  \w     26.00  86.00   1.00    2.99    --   36.77  57.00 -30.00   60
  5  \w     82.00 107.00   1.00    2.99    --   36.77 178.00  90.00   25
  6  \w     10.00  84.00   1.00    2.99    --   36.77  77.00-150.00   74
  7  \w     30.00  63.00   1.00    2.99    --   36.77 -99.00 120.00   33
  8  \w     47.00  74.00   1.00    2.99    --   36.77 -99.00 -90.00   27
  9  \w    -31.00  28.00   1.00    2.99    --   36.77 -38.00   0.00   59
 10  \w     41.00 122.00   1.00   11.97    --  108.00 -45.00 -90.00   81
 11  \w     42.00 124.00   1.00   11.97    --  108.00 -45.00  90.00   82
 12  \w     44.00  92.00   1.00   11.97    --  108.00 -61.00 150.00   48
 13  \w     91.00 137.00   1.00   11.97    --  108.00  45.00  60.00   46
 14  \w    118.00 173.00   1.00   11.97    --  108.00  77.00-120.00   55
 15  \w     62.00  88.00   1.00   11.97    --  108.00 -77.00   0.00   26
 16  \w     40.00 109.00   1.00   11.97    --  108.00 -95.00 -60.00   69
 17  \w     44.00  97.00   1.00   11.97    --  108.00-111.00 -90.00   53
 18  \w    103.00 129.00   1.00   11.97    --  108.00 -77.00   0.00   26
 19  \w     65.00 111.00   1.00   11.97    --  108.00-111.00-180.00   46
 20  \w     38.00 116.00   1.00   11.97    --  108.00 -30.00-180.00   78
 21  \w     45.00 103.00   1.00   11.97    --  108.00-111.00  90.00   58
 22  \w     49.00 172.00   1.00   11.97    --  108.00   0.00-150.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1649857000
_diffrn_orient_matrix_UB_12      0.0686706000
_diffrn_orient_matrix_UB_13      0.0936832000
_diffrn_orient_matrix_UB_21      0.0386985000
_diffrn_orient_matrix_UB_22      0.1173713000
_diffrn_orient_matrix_UB_23      0.0509883000
_diffrn_orient_matrix_UB_31      -0.0464138000
_diffrn_orient_matrix_UB_32      0.0965392000
_diffrn_orient_matrix_UB_33      -0.1167334000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5655
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_min         4.787
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0638P)^2^+0.0807P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2681
_reflns_number_total             3431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00936_si_002.cif
_cod_data_source_block           20190402
_cod_database_code               4038605
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.47
_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:
 C25(H25), C26(H26), C11(H11), C22(H22), C23(H23), C17(H17), C6(H6), C12(H12),
 C3(H3), C4(H4), C13(H13), C16(H16), C5(H5), C15(H15)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              82702
_shelx_hkl_checksum              18529
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.651
_oxdiff_exptl_absorpt_empirical_full_min 0.805