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_7132900
_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 H10 N2'
_chemical_formula_sum            'C17 H10 N2'
_chemical_formula_weight         242.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
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_cell_length_a                   4.50440(10)
_cell_length_b                   12.6636(5)
_cell_length_c                   19.6473(8)
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      71.0840
_cell_measurement_theta_min      3.4820
_cell_volume                     1120.72(7)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     52.00 104.00   0.50    0.76    --   80.07  15.00 150.00  104
  2  \w     55.00 124.00   0.50    0.76    --   80.07  15.00  30.00  138
  3  \w     42.00  89.00   0.50    0.76    --   70.49   0.00 -30.00   94
  4  \w     62.00 119.00   0.50    0.76    --   74.85  15.00-120.00  114
  5  \w     50.00  79.00   0.50    0.76    --   74.85   0.00 -30.00   58
  6  \w     26.00  80.00   0.50    0.76    --   61.96   0.00  30.00  108
  7  \w     31.00  97.00   0.50    0.76    --   61.96   0.00  90.00  132
  8  \w     37.00  95.00   0.50    0.76    --   61.96   0.00 150.00  116
  9  \w     29.00  55.00   0.50    0.76    --   61.96 -95.00 150.00   52
 10  \w     37.00  62.00   0.50    0.76    --   74.85-125.00 150.00   50
 11  \w     65.00  99.00   0.50    0.76    --   70.49-125.00 -30.00   68
 12  \w     39.00  67.00   0.50    0.76    --   80.07-125.00-150.00   56
 13  \w     30.00  56.00   0.50    0.76    --   70.49-125.00 -30.00   52
 14  \w     37.00 108.00   0.50    0.76    --   80.07-125.00-180.00  142
 15  \w     84.00 109.00   0.50    0.76    --   80.07-125.00 -60.00   50
 16  \w     83.00 108.00   0.50    0.76    --   80.07-125.00-150.00   50
 17  \w     38.00  67.00   0.50    0.76    --   80.07-125.00 -60.00   58
 18  \w     34.00  59.00   0.50    0.76    --   70.49-106.00  66.00   50
 19  \w     43.00  68.00   0.50    0.76    --   80.07-106.00  66.00   50
 20  \w     24.00  52.00   0.50    0.76    --   61.96 -95.00  90.00   56
 21  \w     24.00  67.00   0.50    0.76    --   61.96-106.00  66.00   86
 22  \w     73.00 109.00   0.50    0.76    --   80.07-125.00 120.00   72
 23  \w     40.00  65.00   0.50    0.76    --   80.07-125.00 120.00   50
 24  \w     32.00  66.00   0.50    0.76    --   61.96 -95.00 120.00   68
 25  \w     53.00  78.00   0.50    0.76    --   74.85 -95.00   0.00   50
 26  \w     46.00  73.00   0.50    0.76    --   74.85 -95.00 -60.00   54
 27  \w     32.00  63.00   0.50    0.76    --   61.96 -95.00-120.00   62
 28  \w     64.00  89.00   0.50    0.76    --   80.07 -95.00-150.00   50
 29  \w     79.00 104.00   0.50    0.76    --   80.07 125.00  90.00   50
 30  \w    -90.00 -65.00   0.50    0.76    --  -77.57 106.00 165.00   50
 31  \w    -65.00 -28.00   0.50    0.76    --  -64.74 106.00 165.00   74
 32  \w    -68.00 -42.00   0.50    0.76    --  -74.46 106.00 165.00   52
 33  \w    -99.00 -34.00   0.50    0.76    --  -77.57 125.00   0.00  130
 34  \w    -63.00 -37.00   0.50    0.76    --  -74.46 125.00 -60.00   52
 35  \w   -103.00 -78.00   0.50    0.76    --  -74.46 125.00 -60.00   50
 36  \w   -121.00 -93.00   0.50    0.76    --  -77.57-125.00  30.00   56
 37  \w   -119.00 -78.00   0.50    0.76    --  -77.57-125.00  90.00   82
 38  \w   -118.00 -80.00   0.50    0.76    --  -77.57-125.00   0.00   76
 39  \w   -106.00 -74.00   0.50    0.76    --  -77.57-125.00-150.00   64
;
_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      -0.1069165000
_diffrn_orient_matrix_UB_12      -0.0515838000
_diffrn_orient_matrix_UB_13      -0.0667135000
_diffrn_orient_matrix_UB_21      0.0383469000
_diffrn_orient_matrix_UB_22      0.1060613000
_diffrn_orient_matrix_UB_23      -0.0372313000
_diffrn_orient_matrix_UB_31      0.3225682000
_diffrn_orient_matrix_UB_32      -0.0297613000
_diffrn_orient_matrix_UB_33      -0.0177265000
_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  0.0669
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12127
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         4.153
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83994
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.3(13)
_refine_ls_extinction_coef       0.0032(12)
_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   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0919P)^2^+0.3346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1836
_reflns_number_total             2008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           230522lt2_auto
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_database_code               7132900
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.894
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.3(13)
 -0.3(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_shelx_res_checksum              27470
_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 1.668
_oxdiff_exptl_absorpt_empirical_full_min 0.493