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_7132906
_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         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_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             2023-08-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-08-22 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                104.088(3)
_cell_angle_beta                 101.613(2)
_cell_angle_gamma                109.165(3)
_cell_formula_units_Z            2
_cell_length_a                   8.22512(19)
_cell_length_b                   10.0169(4)
_cell_length_c                   12.1195(4)
_cell_measurement_reflns_used    7364
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6990
_cell_measurement_theta_min      3.9400
_cell_volume                     870.66(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (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      99.99(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 0.935
_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     19.00  56.00   0.50    0.05    --   56.25-125.00 -90.00   74
  2  \w     28.00  54.00   0.50    0.05    --   69.31-125.00-120.00   52
  3  \w     15.00  41.00   0.50    0.05    --   56.25-103.00-161.00   52
  4  \w     29.00  54.00   0.50    0.05    --   69.31-103.00-161.00   50
  5  \w     36.00  61.00   0.50    0.05    --   75.94-103.00-161.00   50
  6  \w     64.00  92.00   0.50    0.05    --   83.87-103.00-161.00   56
  7  \w     33.00  58.00   0.50    0.05    --   75.94 -95.00 -90.00   50
  8  \w     17.00  56.00   0.50    0.05    --   56.25 -95.00 -60.00   78
  9  \w     27.00  52.00   0.50    0.05    --   69.31 -95.00  30.00   50
 10  \w     35.00  60.00   0.50    0.05    --   75.94 -95.00  60.00   50
 11  \w     29.00  56.00   0.50    0.05    --   69.31 -95.00  90.00   54
 12  \w     35.00  67.00   0.50    0.05    --   75.94 -95.00 120.00   64
 13  \w     40.00  84.00   0.50    0.05    --   75.94 -95.00 150.00   88
 14  \w     47.00  87.00   0.50    0.05    --   83.87 -95.00 120.00   80
 15  \w     49.00  88.00   0.50    0.05    --   83.87 -95.00  90.00   78
 16  \w     41.00  66.00   0.50    0.05    --   83.87 -95.00  30.00   50
 17  \w     66.00  91.00   0.50    0.05    --   83.87 -95.00   0.00   50
 18  \w     43.00  90.00   0.50    0.05    --   83.87 -95.00 -60.00   94
 19  \w     41.00  92.00   0.50    0.05    --   83.87 -95.00-120.00  102
 20  \w     56.00 127.00   0.50    0.05    --   83.87  15.00   0.00  142
 21  \w     94.00 119.00   0.50    0.05    --   69.31  15.00 -30.00   50
 22  \w     48.00 107.00   0.50    0.05    --   75.94  15.00 -60.00  118
 23  \w     58.00  84.00   0.50    0.05    --   69.31  15.00 -30.00   52
 24  \w     80.00 105.00   0.50    0.05    --   83.87  15.00 120.00   50
 25  \w     37.00  81.00   0.50    0.05    --   56.25  15.00  90.00   88
 26  \w    -64.00 -38.00   0.50    0.05    --  -59.44 -15.00  30.00   52
 27  \w   -126.00 -39.00   0.50    0.05    --  -75.32 -15.00 -30.00  174
 28  \w   -109.00 -73.00   0.50    0.05    --  -59.44 -15.00  30.00   72
 29  \w   -125.00 -48.00   0.50    0.05    --  -75.32 -15.00  60.00  154
 30  \w   -121.00 -88.00   0.50    0.05    --  -72.13 -15.00 120.00   66
 31  \w    -62.00 -36.00   0.50    0.05    --  -72.13 -15.00 120.00   52
 32  \w    -83.00 -56.00   0.50    0.05    --  -75.32 103.00 -59.00   54
 33  \w    -58.00 -33.00   0.50    0.05    --  -75.32 111.00-150.00   50
 34  \w    -97.00 -34.00   0.50    0.05    --  -79.90 115.00 -46.85  126
 35  \w    -97.00 -64.00   0.50    0.05    --  -79.90 114.00  25.30   66
 36  \w    -59.00 -34.00   0.50    0.05    --  -79.90 114.00  25.30   50
 37  \w    -63.00 -36.00   0.50    0.05    --  -75.32 111.00 150.00   54
 38  \w    -52.00 -26.00   0.50    0.05    --  -59.44 103.00 -59.00   52
 39  \w    -56.00 -31.00   0.50    0.05    --  -72.13 103.00 -59.00   50
 40  \w    -92.00 -66.00   0.50    0.05    --  -75.32 111.00-150.00   52
;
_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      -0.0010757000
_diffrn_orient_matrix_UB_12      0.1295215000
_diffrn_orient_matrix_UB_13      -0.0470116000
_diffrn_orient_matrix_UB_21      -0.0055386000
_diffrn_orient_matrix_UB_22      -0.0927760000
_diffrn_orient_matrix_UB_23      -0.1234909000
_diffrn_orient_matrix_UB_31      -0.2082708000
_diffrn_orient_matrix_UB_32      -0.0668390000
_diffrn_orient_matrix_UB_33      -0.0387559000
_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  0.0123
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9944
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.836
_diffrn_reflns_theta_min         3.951
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0093(8)
_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     236
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0412P)^2^+0.2543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3127
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           230861lt_auto
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_original_cell_volume        870.66(5)
_cod_database_code               7132906
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), N9(H9)
;
_shelx_res_checksum              10130
_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 1.119
_oxdiff_exptl_absorpt_empirical_full_min 0.865