Synthesis of two nitrogen-containing polyaromatic compounds through gold catalysis/DBU-promoted cyclizations.
Sadaphal, Vikas Ashokrao; Wu, Tien-Lin; Liu, Rai-Shung; Chemical communications (Cambridge, England) 60 (2024) 4294–4297; doi:10.1039/d4cc00113c

data_7132901
_publ_section_title
;
 Synthesis of two nitrogen-containing polyaromatic compounds through gold
 catalysis/DBU-promoted cyclizations.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4294
_journal_page_last               4297
_journal_paper_doi               10.1039/d4cc00113c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H14 N2 O'
_chemical_formula_sum            'C24 H14 N2 O'
_chemical_formula_weight         346.37
_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             2023-08-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-10 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                106.1712(14)
_cell_angle_beta                 91.1629(11)
_cell_angle_gamma                109.9674(13)
_cell_formula_units_Z            2
_cell_length_a                   7.67160(10)
_cell_length_b                   9.16801(15)
_cell_length_c                   12.73071(19)
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5450
_cell_measurement_theta_min      5.3630
_cell_volume                     801.64(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_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    -72.00 -30.00   0.50    0.05    --  -75.32 111.00  90.00   84
  2  \w    -52.00 -26.00   0.50    0.05    --  -72.13 125.00  60.00   52
  3  \w    -97.00 -34.00   0.50    0.05    --  -79.90 114.00  22.16  126
  4  \w    -62.00 -29.00   0.50    0.05    --  -72.13 125.00   0.00   66
  5  \w    -93.00 -35.00   0.50    0.05    --  -79.90 104.00-178.33  116
  6  \w   -126.00 -42.00   0.50    0.05    --  -75.32 -15.00-150.00  168
  7  \w    -87.00 -36.00   0.50    0.05    --  -59.44 -15.00-120.00  102
  8  \w   -124.00 -40.00   0.50    0.05    --  -75.32 -15.00 120.00  168
  9  \w    -86.00 -37.00   0.50    0.05    --  -59.44 -15.00 120.00   98
 10  \w     23.00  58.00   0.50    0.05    --   56.25-125.00  60.00   70
 11  \w     39.00  64.00   0.50    0.05    --   83.87-111.00  30.00   50
 12  \w     27.00  52.00   0.50    0.05    --   69.31 -95.00 -30.00   50
 13  \w     37.00  82.00   0.50    0.05    --   75.94 -95.00 -30.00   90
 14  \w     34.00  72.00   0.50    0.05    --   75.94 -95.00 -60.00   76
 15  \w     41.00  81.00   0.50    0.05    --   75.94 -95.00-120.00   80
 16  \w     66.00  91.00   0.50    0.05    --   83.87 -95.00-120.00   50
 17  \w     30.00  63.00   0.50    0.05    --   69.31 -95.00-180.00   66
 18  \w     31.00  57.00   0.50    0.05    --   75.94-111.00-150.00   52
 19  \w     14.00  42.00   0.50    0.05    --   56.25 -95.00 -90.00   56
 20  \w     41.00  92.00   0.50    0.05    --   83.87 -95.00 -90.00  102
 21  \w     62.00  92.00   0.50    0.05    --   83.87 -95.00 -30.00   60
 22  \w     41.00  67.00   0.50    0.05    --   83.87 -95.00  30.00   52
 23  \w     48.00  90.00   0.50    0.05    --   83.87 -95.00  90.00   84
 24  \w     54.00  91.00   0.50    0.05    --   83.87 -95.00 120.00   74
 25  \w     54.00  90.00   0.50    0.05    --   83.87 -95.00 150.00   72
 26  \w     49.00 133.00   0.50    0.05    --   83.87  15.00 150.00  168
 27  \w     48.00 132.00   0.50    0.05    --   83.87  15.00  60.00  168
 28  \w     75.00 116.00   0.50    0.05    --   83.87  15.00 -60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0361295000
_diffrn_orient_matrix_UB_12      -0.1838452000
_diffrn_orient_matrix_UB_13      -0.0387809000
_diffrn_orient_matrix_UB_21      0.0767700000
_diffrn_orient_matrix_UB_22      0.0155732000
_diffrn_orient_matrix_UB_23      -0.1088476000
_diffrn_orient_matrix_UB_31      0.1980123000
_diffrn_orient_matrix_UB_32      0.0342211000
_diffrn_orient_matrix_UB_33      0.0527934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8120
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.754
_diffrn_reflns_theta_min         5.388
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0487P)^2^+0.2909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2922
_reflns_number_total             3101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           230766lt_auto
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_database_code               7132901
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.861
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              75901
_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 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.793