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_7132904
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-01 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4803(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.43235(13)
_cell_length_b                   12.20419(15)
_cell_length_c                   11.52302(14)
_cell_measurement_reflns_used    7341
_cell_measurement_temperature    109(6)
_cell_measurement_theta_max      74.2820
_cell_measurement_theta_min      3.5720
_cell_volume                     1707.04(4)
_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      109(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_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     48.00  92.00   0.50    0.05    --   75.94-111.00 150.00   88
  2  \w     58.00  84.00   0.50    0.05    --   83.87-102.00  52.00   52
  3  \w     36.00  61.00   0.50    0.05    --   75.94-102.00  52.00   50
  4  \w     14.00  39.00   0.50    0.05    --   56.25 -95.00 150.00   50
  5  \w     48.00  80.00   0.50    0.05    --   69.31-102.00  52.00   64
  6  \w     55.00  83.00   0.50    0.05    --   83.87 -95.00 150.00   56
  7  \w     12.00  68.00   0.50    0.05    --   56.25-102.00  52.00  112
  8  \w     54.00  83.00   0.50    0.05    --   83.87 -95.00  90.00   58
  9  \w     47.00  91.00   0.50    0.05    --   83.87 -95.00   0.00   88
 10  \w     14.00  52.00   0.50    0.05    --   56.25 -95.00-120.00   76
 11  \w     32.00  76.00   0.50    0.05    --   69.31 -95.00-150.00   88
 12  \w     50.00  92.00   0.50    0.05    --   83.87 -95.00-120.00   84
 13  \w     53.00 117.00   0.50    0.05    --   83.87  15.00  90.00  128
 14  \w     60.00 110.00   0.50    0.05    --   69.31  15.00  30.00  100
 15  \w     70.00  95.00   0.50    0.05    --   83.87  15.00 -60.00   50
 16  \w     98.00 134.00   0.50    0.05    --   83.87  15.00 -60.00   72
 17  \w     81.00 126.00   0.50    0.05    --   75.94  15.00-150.00   90
 18  \w     51.00 111.00   0.50    0.05    --   75.94  15.00-180.00  120
 19  \w    -87.00 -30.00   0.50    0.05    --  -75.32 111.00 -60.00  114
 20  \w    -91.00 -39.00   0.50    0.05    --  -75.32 -15.00-150.00  104
 21  \w    -80.00 -55.00   0.50    0.05    --  -72.13 102.00 155.00   50
 22  \w    -78.00 -52.00   0.50    0.05    --  -75.32 102.00 155.00   52
 23  \w    -50.00 -25.00   0.50    0.05    --  -59.44 102.00 155.00   50
;
_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      -0.0421176000
_diffrn_orient_matrix_UB_12      0.0301352000
_diffrn_orient_matrix_UB_13      -0.1318977000
_diffrn_orient_matrix_UB_21      -0.0459372000
_diffrn_orient_matrix_UB_22      -0.1168236000
_diffrn_orient_matrix_UB_23      -0.0254156000
_diffrn_orient_matrix_UB_31      -0.1105478000
_diffrn_orient_matrix_UB_32      0.0371625000
_diffrn_orient_matrix_UB_33      0.0267127000
_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  0.0265
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.736
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92640
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0027(3)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0414P)^2^+0.4946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3024
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           230884lt_auto
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_database_code               7132904
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.862
_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:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), N9(H9)
;
_shelx_res_checksum              8875
_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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.790