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_7132903
_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 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-23 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.071(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3278(3)
_cell_length_b                   7.4345(2)
_cell_length_c                   21.1425(4)
_cell_measurement_reflns_used    5360
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6350
_cell_measurement_theta_min      4.2140
_cell_volume                     2534.37(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     60.00  85.00   0.50    0.17    --   61.65  25.00 106.00   50
  2  \w    -93.00 -67.00   0.50    0.17    --  -64.43 -25.00 -57.00   52
  3  \w     66.00  91.00   0.50    0.17    --   70.49  25.00 106.00   50
  4  \w   -122.00 -75.00   0.50    0.17    --  -74.46 -25.00 -57.00   94
  5  \w     79.00 104.00   0.50    0.17    --   74.66  25.00 106.00   50
  6  \w   -121.00 -96.00   0.50    0.17    --  -77.38 -25.00 -57.00   50
  7  \w     73.00 127.00   0.50    0.17    --   80.07  25.00 106.00  108
  8  \w     35.00  61.00   0.50    0.17    --   61.65 -95.00-180.00   52
  9  \w     28.00  57.00   0.50    0.17    --   61.65 -95.00-120.00   58
 10  \w     30.00 105.00   0.50    0.17    --   61.65  15.00-150.00  150
 11  \w   -108.00 -33.00   0.50    0.17    --  -64.43 -15.00-180.00  150
 12  \w     34.00 105.00   0.50    0.17    --   70.49   0.00 -90.00  142
 13  \w     38.00  82.00   0.50    0.17    --   74.66 -95.00 -90.00   88
 14  \w     43.00  69.00   0.50    0.17    --   74.66 -95.00-180.00   52
 15  \w     43.00  78.00   0.50    0.17    --   74.66 -95.00   0.00   70
 16  \w     39.00  83.00   0.50    0.17    --   74.66 -95.00  90.00   88
 17  \w     42.00  83.00   0.50    0.17    --   74.66 -95.00-150.00   82
 18  \w   -118.00 -74.00   0.50    0.17    --  -77.38-125.00-180.00   88
 19  \w     87.00 112.00   0.50    0.17    --   80.07 125.00-180.00   50
 20  \w     55.00  88.00   0.50    0.17    --   80.07 -95.00 120.00   66
 21  \w     79.00 124.00   0.50    0.17    --   80.07 125.00 150.00   90
 22  \w     44.00  86.00   0.50    0.17    --   80.07 -95.00 -60.00   84
;
_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      -0.0305537000
_diffrn_orient_matrix_UB_12      0.0601635000
_diffrn_orient_matrix_UB_13      -0.0694421000
_diffrn_orient_matrix_UB_21      0.0904901500
_diffrn_orient_matrix_UB_22      0.0277552500
_diffrn_orient_matrix_UB_23      -0.0102907000
_diffrn_orient_matrix_UB_31      0.0034631000
_diffrn_orient_matrix_UB_32      -0.1962887000
_diffrn_orient_matrix_UB_33      -0.0227216000
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8719
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.235
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
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    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00065(11)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0616P)^2^+1.3174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1954
_reflns_number_total             2263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           230521lt_auto
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_database_code               7132903
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.886
_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:
 C2(H2), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C19(H19), N9(H9)
;
_shelx_res_checksum              63306
_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 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.701