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_7132907
_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         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-16 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.580(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6032(6)
_cell_length_b                   3.85280(10)
_cell_length_c                   18.9019(6)
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      73.7850
_cell_measurement_theta_min      3.1220
_cell_volume                     1264.08(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 (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      99.9(3)
_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 0.982
_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     36.00  62.00   0.50    2.30    --   56.25-115.00-147.00   52
  2  \w    -49.00 -19.00   0.50    2.30    --  -59.44 115.00 -57.00   60
  3  \w     33.00  58.00   0.50    2.30    --   69.31-115.00-147.00   50
  4  \w    -83.00 -58.00   0.50    2.30    --  -72.13 115.00 -57.00   50
  5  \w    -92.00 -48.00   0.50    2.30    --  -75.32 115.00 -57.00   88
  6  \w     63.00  88.00   0.50    2.30    --   75.94-115.00-147.00   50
  7  \w     71.00  97.00   0.50    2.30    --   83.87-115.00-147.00   52
  8  \w     14.00  63.00   0.50    2.30    --   56.25 -95.00  30.00   98
  9  \w     31.00  56.00   0.50    2.30    --   56.25-125.00 -60.00   50
 10  \w     15.00  63.00   0.50    2.30    --   56.25 -95.00 -30.00   96
 11  \w     53.00  78.00   0.50    2.30    --   56.25  15.00 -90.00   50
 12  \w     26.00  83.00   0.50    2.30    --   56.25-125.00-180.00  114
 13  \w     18.00  43.00   0.50    2.30    --   56.25 -95.00 -90.00   50
 14  \w     16.00  48.00   0.50    2.30    --   56.25 -95.00  90.00   64
 15  \w   -108.00 -41.00   0.50    2.30    --  -59.44 -15.00  90.00  134
 16  \w    -67.00 -26.00   0.50    2.30    --  -72.13 125.00  60.00   82
 17  \w    -59.00 -26.00   0.50    2.30    --  -72.13 125.00   0.00   66
 18  \w    -98.00 -72.00   0.50    2.30    --  -72.13 125.00  60.00   52
 19  \w   -103.00 -40.00   0.50    2.30    --  -75.32 -15.00 150.00  126
 20  \w   -126.00 -58.00   0.50    2.30    --  -75.32 -15.00-120.00  136
 21  \w   -126.00 -53.00   0.50    2.30    --  -75.32 -15.00  30.00  146
 22  \w   -126.00 -40.00   0.50    2.30    --  -75.32 -15.00 -60.00  172
 23  \w     53.00  83.00   0.50    2.30    --   75.94 -95.00 120.00   60
 24  \w     37.00  82.00   0.50    2.30    --   75.94 -95.00  60.00   90
 25  \w     34.00  82.00   0.50    2.30    --   75.94 -95.00-150.00   96
 26  \w     33.00  58.00   0.50    2.30    --   75.94 -95.00 -60.00   50
 27  \w    -97.00 -42.00   0.50    2.30    --  -79.90 114.00-104.12  110
 28  \w     66.00  91.00   0.50    2.30    --   83.87 -95.00  60.00   50
 29  \w     41.00  92.00   0.50    2.30    --   83.87 -95.00-150.00  102
 30  \w     58.00  92.00   0.50    2.30    --   83.87 -95.00 120.00   68
 31  \w     43.00  92.00   0.50    2.30    --   83.87 -95.00-120.00   98
 32  \w     39.00  64.00   0.50    2.30    --   83.87-111.00 -90.00   50
 33  \w     67.00  92.00   0.50    2.30    --   83.87 -95.00  90.00   50
 34  \w     41.00  92.00   0.50    2.30    --   83.87 -95.00 150.00  102
 35  \w     41.00  92.00   0.50    2.30    --   83.87 -95.00   0.00  102
 36  \w     43.00  91.00   0.50    2.30    --   83.87 -95.00 -90.00   96
 37  \w     51.00 106.00   0.50    2.30    --   83.87  15.00  90.00  110
 38  \w     56.00 134.00   0.50    2.30    --   83.87  15.00 -60.00  156
 39  \w     42.00  92.00   0.50    2.30    --   83.87 -95.00 -30.00  100
 40  \w     39.00  66.00   0.50    2.30    --   83.87-111.00 120.00   54
 41  \w     42.00  92.00   0.50    2.30    --   83.87 -95.00  30.00  100
 42  \w     42.00  68.00   0.50    2.30    --   83.87 -95.00-180.00   52
 43  \w     50.00 130.00   0.50    2.30    --   83.87  15.00-150.00  160
;
_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      -0.0765264000
_diffrn_orient_matrix_UB_12      -0.1407716000
_diffrn_orient_matrix_UB_13      0.0177174000
_diffrn_orient_matrix_UB_21      0.0368329000
_diffrn_orient_matrix_UB_22      -0.0328082000
_diffrn_orient_matrix_UB_23      0.0795933000
_diffrn_orient_matrix_UB_31      -0.0256056000
_diffrn_orient_matrix_UB_32      0.3729789000
_diffrn_orient_matrix_UB_33      0.0136741000
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17727
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.864
_diffrn_reflns_theta_min         3.177
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67574
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1064P)^2^+0.4753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2234
_reflns_number_total             2556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00113c2.cif
_cod_data_source_block           231019lt
_cod_depositor_comments
'Adding full bibliography for 7132900--7132907.cif.'
_cod_database_code               7132907
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b X=CH2 refined with riding coordinates:
 C21(H21A,H21B)
;
_shelx_res_checksum              51522
_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 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.493