##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
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data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2010-03-03
_journal_date_accepted     2010-05-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1793
_journal_page_last     o1793
_journal_paper_category     QO
_journal_coeditor_code     NK2028
_publ_contact_author_name     'Dr P.A. Crooks'
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
_publ_contact_author_email     'pcrooks@uky.edu'
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;
(E,E)-1-Methyl-2,6-distyrylpyridinium iodide
;
loop_
    _publ_author_name
    _publ_author_address
    'Narsimha Reddy Penthala'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Joshua Eldridge'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Thirupathi Reddy Yerram Reddy'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E,E)-1-Methyl-2,6-distyrylpyridinium iodide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H20 N +, I -'
_chemical_formula_sum     'C22 H20 I N'
_chemical_formula_iupac     'C22 H20 N +, I -'
_chemical_formula_weight     425.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     18.7309(4)
_cell_length_b     9.5687(2)
_cell_length_c     19.9829(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.2790(10)
_cell_angle_gamma     90.00
_cell_volume     3581.50(13)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9883
_cell_measurement_theta_min     4.43
_cell_measurement_theta_max     68.52
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     'shard'
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.577
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1696
_exptl_absorpt_coefficient_mu     14.042
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS in APEX2; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.211
_exptl_absorpt_correction_T_max     0.400
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus rotating anode'
_diffrn_radiation_monochromator     'graded multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     5.6
_diffrn_reflns_number     24972
_diffrn_reflns_av_R_equivalents     0.0425
_diffrn_reflns_av_sigmaI/netI     0.0228
_diffrn_reflns_theta_min     4.43
_diffrn_reflns_theta_max     68.51
_diffrn_reflns_theta_full     68.51
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total     3303
_reflns_number_gt     3286
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0206
_refine_ls_R_factor_gt     0.0205
_refine_ls_wR_factor_gt     0.0550
_refine_ls_wR_factor_ref     0.0551
_refine_ls_goodness_of_fit_ref     1.090
_refine_ls_restrained_S_all     1.090
_refine_ls_number_reflns     3303
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0309P)²+5.1348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.578
_refine_diff_density_min     -0.487
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.000067(15)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.3257 6.8362
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and local procedures
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.157566(6) 0.613743(12) 0.396017(5) 0.01533(8) Uani d . 1 . .
    N N1 0.38671(8) 0.46130(16) 0.46816(7) 0.0115(3) Uani d . 1 . .
    C C1 0.36127(12) 0.60507(19) 0.45527(12) 0.0192(5) Uani d . 1 . .
    H H1A 0.4014 0.6634 0.4410 0.029 Uiso calc R 1 . .
    H H1B 0.3407 0.6437 0.4963 0.029 Uiso calc R 1 . .
    H H1C 0.3248 0.6034 0.4199 0.029 Uiso calc R 1 . .
    C C2 0.44830(10) 0.4136(2) 0.43884(9) 0.0133(4) Uani d . 1 . .
    C C3 0.47346(10) 0.2818(2) 0.45649(9) 0.0153(4) Uani d . 1 . .
    H H3 0.5164 0.2477 0.4374 0.018 Uiso calc R 1 . .
    C C4 0.43651(10) 0.2005(2) 0.50154(9) 0.0146(4) Uani d . 1 . .
    H H4 0.4544 0.1112 0.5139 0.018 Uiso calc R 1 . .
    C C5 0.37368(10) 0.24873(19) 0.52856(9) 0.0136(4) Uani d . 1 . .
    H H5 0.3477 0.1915 0.5588 0.016 Uiso calc R 1 . .
    C C6 0.34807(11) 0.37993(18) 0.51204(10) 0.0120(4) Uani d . 1 . .
    C C7 0.28002(10) 0.4316(2) 0.53757(9) 0.0133(4) Uani d . 1 . .
    H H7 0.2554 0.5026 0.5135 0.016 Uiso calc R 1 . .
    C C8 0.25134(11) 0.38157(18) 0.59407(10) 0.0146(4) Uani d . 1 . .
    H H8 0.2794 0.3177 0.6194 0.018 Uiso calc R 1 . .
    C C9 0.18083(10) 0.4165(2) 0.62012(9) 0.0139(4) Uani d . 1 . .
    C C10 0.15174(11) 0.3314(2) 0.67007(10) 0.0177(4) Uani d . 1 . .
    H H10 0.1795 0.2576 0.6884 0.021 Uiso calc R 1 . .
    C C11 0.08281(11) 0.3536(2) 0.69312(10) 0.0191(4) Uani d . 1 . .
    H H11 0.0636 0.2945 0.7267 0.023 Uiso calc R 1 . .
    C C12 0.04199(10) 0.4616(2) 0.66730(10) 0.0180(4) Uani d . 1 . .
    H H12 -0.0055 0.4758 0.6823 0.022 Uiso calc R 1 . .
    C C13 0.07150(11) 0.5492(2) 0.61904(9) 0.0169(4) Uani d . 1 . .
    H H13 0.0442 0.6250 0.6021 0.020 Uiso calc R 1 . .
    C C14 0.13969(10) 0.5276(2) 0.59548(9) 0.0154(4) Uani d . 1 . .
    H H14 0.1588 0.5882 0.5625 0.018 Uiso calc R 1 . .
    C C15 0.48534(11) 0.5004(2) 0.38947(10) 0.0189(4) Uani d . 1 . .
    H H15 0.4637 0.5858 0.3760 0.023 Uiso calc R 1 . .
    C C16 0.54716(11) 0.4660(2) 0.36280(10) 0.0183(4) Uani d . 1 . .
    H H16 0.5664 0.3784 0.3761 0.022 Uiso calc R 1 . .
    C C17 0.58969(10) 0.5469(2) 0.31504(9) 0.0150(4) Uani d . 1 . .
    C C18 0.64612(11) 0.4793(2) 0.28280(10) 0.0168(4) Uani d . 1 . .
    H H18 0.6546 0.3828 0.2909 0.020 Uiso calc R 1 . .
    C C19 0.68995(11) 0.5521(2) 0.23897(10) 0.0188(4) Uani d . 1 . .
    H H19 0.7273 0.5047 0.2163 0.023 Uiso calc R 1 . .
    C C20 0.67921(11) 0.6936(2) 0.22840(10) 0.0190(4) Uani d . 1 . .
    H H20 0.7094 0.7435 0.1987 0.023 Uiso calc R 1 . .
    C C21 0.62407(11) 0.7629(2) 0.26133(10) 0.0209(4) Uani d . 1 . .
    H H21 0.6173 0.8603 0.2547 0.025 Uiso calc R 1 . .
    C C22 0.57920(11) 0.6895(2) 0.30369(10) 0.0171(4) Uani d . 1 . .
    H H22 0.5410 0.7366 0.3252 0.020 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C2 . 1.374(2) ?
    N1 C6 . 1.380(2) ?
    N1 C1 . 1.478(2) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 C3 . 1.391(3) ?
    C2 C15 . 1.467(3) ?
    C3 C4 . 1.379(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.377(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.383(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.461(3) ?
    C7 C8 . 1.341(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.461(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.401(3) ?
    C9 C14 . 1.401(3) ?
    C10 C11 . 1.389(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.384(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.394(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.379(3) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.319(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.467(3) ?
    C16 H16 . 0.9500 ?
    C17 C22 . 1.397(3) ?
    C17 C18 . 1.399(3) ?
    C18 C19 . 1.391(3) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.385(3) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.395(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.387(3) ?
    C21 H21 . 0.9500 ?
    C22 H22 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 N1 C6 . . 121.83(16) ?
    C2 N1 C1 . . 120.35(16) ?
    C6 N1 C1 . . 117.78(16) ?
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C3 . . 118.49(17) ?
    N1 C2 C15 . . 119.95(17) ?
    C3 C2 C15 . . 121.55(17) ?
    C4 C3 C2 . . 120.45(18) ?
    C4 C3 H3 . . 119.8 ?
    C2 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 119.95(18) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.46(17) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    N1 C6 C5 . . 118.76(17) ?
    N1 C6 C7 . . 119.48(16) ?
    C5 C6 C7 . . 121.71(17) ?
    C8 C7 C6 . . 121.80(18) ?
    C8 C7 H7 . . 119.1 ?
    C6 C7 H7 . . 119.1 ?
    C7 C8 C9 . . 125.79(18) ?
    C7 C8 H8 . . 117.1 ?
    C9 C8 H8 . . 117.1 ?
    C10 C9 C14 . . 118.44(18) ?
    C10 C9 C8 . . 118.45(18) ?
    C14 C9 C8 . . 123.05(17) ?
    C11 C10 C9 . . 120.86(19) ?
    C11 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 119.6 ?
    C12 C11 C10 . . 120.22(19) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C11 C12 C13 . . 119.12(18) ?
    C11 C12 H12 . . 120.4 ?
    C13 C12 H12 . . 120.4 ?
    C14 C13 C12 . . 121.16(18) ?
    C14 C13 H13 . . 119.4 ?
    C12 C13 H13 . . 119.4 ?
    C13 C14 C9 . . 120.16(18) ?
    C13 C14 H14 . . 119.9 ?
    C9 C14 H14 . . 119.9 ?
    C16 C15 C2 . . 123.32(18) ?
    C16 C15 H15 . . 118.3 ?
    C2 C15 H15 . . 118.3 ?
    C15 C16 C17 . . 127.73(19) ?
    C15 C16 H16 . . 116.1 ?
    C17 C16 H16 . . 116.1 ?
    C22 C17 C18 . . 118.89(17) ?
    C22 C17 C16 . . 122.98(17) ?
    C18 C17 C16 . . 118.00(18) ?
    C19 C18 C17 . . 120.53(19) ?
    C19 C18 H18 . . 119.7 ?
    C17 C18 H18 . . 119.7 ?
    C20 C19 C18 . . 120.00(18) ?
    C20 C19 H19 . . 120.0 ?
    C18 C19 H19 . . 120.0 ?
    C19 C20 C21 . . 120.00(18) ?
    C19 C20 H20 . . 120.0 ?
    C21 C20 H20 . . 120.0 ?
    C22 C21 C20 . . 119.98(19) ?
    C22 C21 H21 . . 120.0 ?
    C20 C21 H21 . . 120.0 ?
    C21 C22 C17 . . 120.56(18) ?
    C21 C22 H22 . . 119.7 ?
    C17 C22 H22 . . 119.7 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 N1 C2 C3 . . . . -2.8(3) ?
    C1 N1 C2 C3 . . . . 174.87(18) ?
    C6 N1 C2 C15 . . . . 176.36(17) ?
    C1 N1 C2 C15 . . . . -6.0(3) ?
    N1 C2 C3 C4 . . . . 1.1(3) ?
    C15 C2 C3 C4 . . . . -178.04(18) ?
    C2 C3 C4 C5 . . . . 1.0(3) ?
    C3 C4 C5 C6 . . . . -1.5(3) ?
    C2 N1 C6 C5 . . . . 2.3(3) ?
    C1 N1 C6 C5 . . . . -175.42(18) ?
    C2 N1 C6 C7 . . . . -175.13(17) ?
    C1 N1 C6 C7 . . . . 7.1(3) ?
    C4 C5 C6 N1 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . 177.27(18) ?
    N1 C6 C7 C8 . . . . -158.92(18) ?
    C5 C6 C7 C8 . . . . 23.7(3) ?
    C6 C7 C8 C9 . . . . -173.77(18) ?
    C7 C8 C9 C10 . . . . 164.66(19) ?
    C7 C8 C9 C14 . . . . -12.5(3) ?
    C14 C9 C10 C11 . . . . 2.1(3) ?
    C8 C9 C10 C11 . . . . -175.20(18) ?
    C9 C10 C11 C12 . . . . -0.6(3) ?
    C10 C11 C12 C13 . . . . -1.3(3) ?
    C11 C12 C13 C14 . . . . 1.8(3) ?
    C12 C13 C14 C9 . . . . -0.2(3) ?
    C10 C9 C14 C13 . . . . -1.7(3) ?
    C8 C9 C14 C13 . . . . 175.49(18) ?
    N1 C2 C15 C16 . . . . 175.08(19) ?
    C3 C2 C15 C16 . . . . -5.8(3) ?
    C2 C15 C16 C17 . . . . -177.77(19) ?
    C15 C16 C17 C22 . . . . 17.0(3) ?
    C15 C16 C17 C18 . . . . -167.2(2) ?
    C22 C17 C18 C19 . . . . -1.5(3) ?
    C16 C17 C18 C19 . . . . -177.53(18) ?
    C17 C18 C19 C20 . . . . 1.9(3) ?
    C18 C19 C20 C21 . . . . -0.5(3) ?
    C19 C20 C21 C22 . . . . -1.2(3) ?
    C20 C21 C22 C17 . . . . 1.5(3) ?
    C18 C17 C22 C21 . . . . -0.2(3) ?
    C16 C17 C22 C21 . . . . 175.62(19) ?
