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_4028266
_publ_contact_author_name
;
;
_publ_section_title
;
 Comprehensive Experimental Study of N-Heterocyclic \p-Stacking
 Interactions of Neutral and Cationic Pyridines
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_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         'C39 H27 N3 O5'
_chemical_formula_sum            'C39 H27 N3 O5'
_chemical_formula_weight         617.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-02-29
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.0920(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4642(10)
_cell_length_b                   12.4255(9)
_cell_length_c                   18.3069(13)
_cell_measurement_reflns_used    4970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.166
_cell_measurement_theta_min      2.285
_cell_volume                     2911.3(4)
_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
;
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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42927
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.59
_diffrn_source                   'sealed tube'
_diffrn_source_current           39.0
_diffrn_source_power             1.833
_diffrn_source_target            Mo
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.847536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.1094 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.8475.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0482P)^2^+1.9088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                4685
_reflns_number_total             5959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400370e_si_005.cif
_cod_data_source_block           lpb9s
_cod_database_code               4028266