Comprehensive Experimental Study of N-Heterocyclic π-Stacking Interactions of Neutral and Cationic Pyridines
Ping Li; Chen Zhao; Mark D. Smith; Ken D. Shimizu; Journal of Organic Chemistry 78 (2013) 5303–5313; doi:10.1021/jo400370e

data_4028265
_publ_section_title
;
 Comprehensive Experimental Study of N-Heterocyclic \p-Stacking
 Interactions of Neutral and Cationic Pyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5303
_journal_page_last               5313
_journal_paper_doi               10.1021/jo400370e
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C33 H23 N3 O4, C2 D3 N, C D Cl3'
_chemical_formula_sum            'C36 H23 Cl3 D4 N4 O4'
_chemical_formula_weight         689.99
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.0050(10)
_cell_angle_beta                 75.1630(10)
_cell_angle_gamma                76.8390(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2269(5)
_cell_length_b                   12.1529(7)
_cell_length_c                   15.1197(8)
_cell_measurement_reflns_used    7495
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.461
_cell_measurement_theta_min      2.248
_cell_volume                     1595.11(15)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_molecular_graphics    various
_computing_publication_material  'SHELXTL Version 6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25261
_diffrn_reflns_theta_full        27.70
_diffrn_reflns_theta_max         27.70
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         7444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                5408
_reflns_number_total             7444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400370e_si_004.cif
_cod_data_source_block           lpa197m
_cod_database_code               4028265