A new class of N-doped ionic PAHs via intramolecular [4+2]-cycloaddition between arylpyridines and alkynes.
Mule, Ravindra D.; Shaikh, Aslam C.; Gade, Amol B.; Patil, Nitin T.; Chemical communications (Cambridge, England) 54 (2018) 11909–11912; doi:10.1039/c8cc05743e

data_7122373
_publ_section_title
;
 A new class of N-doped ionic PAHs via intramolecular [4+2]-cycloaddition
 between arylpyridines and alkynes.
;
_journal_issue                   84
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11909
_journal_page_last               11912
_journal_paper_doi               10.1039/c8cc05743e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C F3 O3 S, C30 H20 N O'
_chemical_formula_sum            'C31 H21 F3 N3 O3 S'
_chemical_formula_weight         559.54
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-12
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2018-02-15 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.425(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.0551(3)
_cell_length_b                   29.5519(9)
_cell_length_c                   20.7844(6)
_cell_measurement_reflns_used    5147
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.2420
_cell_measurement_theta_min      3.8520
_cell_volume                     5486.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.8330
_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     23.00  49.00   1.00   38.16    --   19.75 -77.00 -60.00   26
  2  \w    -31.00  -5.00   1.00   38.16    --  -20.06 -57.00-150.00   26
  3  \w    -50.00  -3.00   1.00   38.16    --   19.75 -77.00-150.00   47
  4  \w     -4.00  91.00   1.00   38.16    --   19.75  77.00  60.00   95
  5  \w     -5.00  37.00   1.00   38.16    --   19.75  77.00-180.00   42
  6  \w    -74.00 -46.00   1.00   38.16    --  -20.06 164.00 112.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0179827000
_diffrn_orient_matrix_UB_12      -0.0041931000
_diffrn_orient_matrix_UB_13      -0.0339836000
_diffrn_orient_matrix_UB_21      -0.0136451000
_diffrn_orient_matrix_UB_22      0.0234294000
_diffrn_orient_matrix_UB_23      -0.0056072000
_diffrn_orient_matrix_UB_31      0.0761324000
_diffrn_orient_matrix_UB_32      0.0032042000
_diffrn_orient_matrix_UB_33      -0.0031284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6269
_diffrn_reflns_theta_full        29.30
_diffrn_reflns_theta_max         29.30
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1176P)^2^+2.3496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2198
_reflns_number_gt                4464
_reflns_number_total             6269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc05743e2.cif
_cod_data_source_block           aslambhai2
_cod_depositor_comments
'Adding full bibliography for 7122372--7122373.cif.'
_cod_database_code               7122373
_chemical_oxdiff_formula         'C10 H10 N10 O10 S10 F10'
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.619
_oxdiff_exptl_absorpt_empirical_full_min 0.586