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_7132905
_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         'C17 H9 N3 O'
_chemical_formula_sum            'C17 H9 N3 O'
_chemical_formula_weight         271.27
_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             2023-10-17
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-10-17 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.565(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.77916(13)
_cell_length_b                   16.2226(5)
_cell_length_c                   19.1757(6)
_cell_measurement_reflns_used    3179
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2430
_cell_measurement_theta_min      3.5780
_cell_volume                     1173.35(7)
_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-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.997
_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     35.00  77.00   0.50    0.17    --   75.94 -95.00-150.00   84
  2  \w     39.00  65.00   0.50    0.17    --   83.87-111.00-150.00   52
  3  \w     16.00  41.00   0.50    0.17    --   56.05 -95.00 -90.00   50
  4  \w     53.00  88.00   0.50    0.17    --   83.87 -95.00-120.00   70
  5  \w     15.00  58.00   0.50    0.17    --   56.05 -95.00   0.00   86
  6  \w     30.00  67.00   0.50    0.17    --   69.01 -95.00  60.00   74
  7  \w     33.00  60.00   0.50    0.17    --   75.94 -95.00  60.00   54
  8  \w     49.00  83.00   0.50    0.17    --   83.87 -95.00  90.00   68
  9  \w     53.00  79.00   0.50    0.17    --   75.94  15.00   0.00   52
 10  \w     49.00 120.00   0.50    0.17    --   83.87  15.00-150.00  142
 11  \w     77.00 120.00   0.50    0.17    --   83.87  15.00 -60.00   86
 12  \w     55.00 126.00   0.50    0.17    --   75.94  15.00 150.00  142
 13  \w    -90.00 -61.00   0.50    0.17    --  -75.32 -15.00 -60.00   58
 14  \w   -126.00 -95.00   0.50    0.17    --  -75.32 -15.00 -60.00   62
 15  \w    -92.00 -31.00   0.50    0.17    --  -75.32 111.00 -90.00  122
 16  \w    -91.00 -31.00   0.50    0.17    --  -75.32 111.00 120.00  120
;
_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      0.3373883000
_diffrn_orient_matrix_UB_12      -0.0130433000
_diffrn_orient_matrix_UB_13      -0.0398027000
_diffrn_orient_matrix_UB_21      0.1218676000
_diffrn_orient_matrix_UB_22      -0.0680278000
_diffrn_orient_matrix_UB_23      0.0521344000
_diffrn_orient_matrix_UB_31      -0.1953598000
_diffrn_orient_matrix_UB_32      -0.0649102000
_diffrn_orient_matrix_UB_33      -0.0467036000
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6065
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.802
_diffrn_reflns_theta_min         3.572
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85955
_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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0572P)^2^+0.1630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1756
_reflns_number_total             2257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           231041lt_auto
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_original_cell_volume        1173.34(7)
_cod_database_code               7132905
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.931
_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)
;
_shelx_res_checksum              99231
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.850