#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/13/2231309.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2231309
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chanawanno, Kullapa'
'Chantrapromma, Suchada'
_publ_section_title
;
 (E)-2-[4-(Dimethylamino)styryl]-1-methylpyridinium triiodide
;
_journal_coeditor_code           SJ5182
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2151
_journal_paper_doi               10.1107/S1600536811028753
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H19 N2 +, I3 -'
_chemical_formula_moiety         'C16 H19 N2, I3'
_chemical_formula_sum            'C16 H19 I3 N2'
_chemical_formula_weight         620.03
_chemical_melting_point_gt       537
_chemical_name_systematic
;
(E)-2-[4-(Dimethylamino)styryl]-1-methylpyridinium triiodide
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.1070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.8760(3)
_cell_length_b                   6.61260(10)
_cell_length_c                   14.4421(2)
_cell_measurement_reflns_used    2484
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.42
_cell_volume                     1890.62(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16143
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.956
_exptl_absorpt_correction_T_max  0.8379
_exptl_absorpt_correction_T_min  0.2119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    2.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.744
_refine_diff_density_min         -0.603
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+13.6577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                2263
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5182.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2231309
_cod_database_fobs_code          2231309
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_symmetry_multiplicity
I I1 0.5000 0.5000 0.0000 0.02351(12) Uani d S 1 4
I I2 0.424696(18) 0.5000 0.16345(3) 0.03339(11) Uani d S 1 2
I I3 0.5000 0.5000 0.5000 0.03354(14) Uani d S 1 4
I I4 0.35817(2) 0.5000 0.42352(3) 0.03813(12) Uani d S 1 2
N N1 0.2700(3) 0.0000 1.2529(3) 0.0300(10) Uani d S 1 2
N N2 0.4157(3) 0.0000 0.6794(4) 0.0393(12) Uani d S 1 2
C C1 0.2277(3) 0.0000 1.3233(4) 0.0338(13) Uani d S 1 2
H H1A 0.2472 0.0000 1.3858 0.041 Uiso calc SR 1 2
C C2 0.1609(3) 0.0000 1.3078(4) 0.0356(13) Uani d S 1 2
H H2A 0.1331 0.0000 1.3580 0.043 Uiso calc SR 1 2
C C3 0.1319(3) 0.0000 1.2140(4) 0.0329(12) Uani d S 1 2
H H3A 0.0842 0.0000 1.2007 0.039 Uiso calc SR 1 2
C C4 0.1724(3) 0.0000 1.1446(4) 0.0319(12) Uani d S 1 2
H H4A 0.1530 0.0000 1.0820 0.038 Uiso calc SR 1 2
C C5 0.2453(3) 0.0000 1.1631(4) 0.0288(11) Uani d S 1 2
C C6 0.2883(3) 0.0000 1.0881(4) 0.0255(10) Uani d S 1 2
H H6A 0.3355 0.0000 1.1052 0.031 Uiso calc SR 1 2
C C7 0.2692(3) 0.0000 0.9977(4) 0.0275(11) Uani d S 1 2
H H7A 0.2218 0.0000 0.9817 0.033 Uiso calc SR 1 2
C C8 0.3107(3) 0.0000 0.9192(4) 0.0290(11) Uani d S 1 2
C C9 0.2775(3) 0.0000 0.8304(4) 0.0289(11) Uani d S 1 2
H H9A 0.2295 0.0000 0.8240 0.035 Uiso calc SR 1 2
C C10 0.3105(3) 0.0000 0.7535(4) 0.0272(11) Uani d S 1 2
H H10A 0.2852 0.0000 0.6945 0.033 Uiso calc SR 1 2
C C11 0.3815(3) 0.0000 0.7579(4) 0.0232(10) Uani d S 1 2
C C12 0.4171(3) 0.0000 0.8475(4) 0.0272(11) Uani d S 1 2
H H12A 0.4651 0.0000 0.8536 0.033 Uiso calc SR 1 2
C C13 0.3818(3) 0.0000 0.9268(4) 0.0336(12) Uani d S 1 2
H H13A 0.4059 0.0000 0.9866 0.040 Uiso calc SR 1 2
C C14 0.3424(3) 0.0000 1.2755(5) 0.0361(13) Uani d S 1 2
H H14A 0.3599 0.1166 1.2461 0.043 Uiso d R 1 1
H H14B 0.3546 0.0000 1.3414 0.043 Uiso d SR 1 2
C C15 0.3804(4) 0.0000 0.5885(4) 0.0391(14) Uani d S 1 2
H H15A 0.3516 0.1166 0.5844 0.047 Uiso d R 1 1
H H15B 0.4110 0.0000 0.5407 0.047 Uiso d SR 1 2
C C16 0.4903(3) 0.0000 0.6862(5) 0.0460(16) Uani d S 1 2
H H16A 0.5052 0.1166 0.7219 0.055 Uiso d R 1 1
H H16B 0.5073 0.0000 0.6261 0.055 Uiso d SR 1 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
I2 I1 I2 5_665 . 180.000(12)
I4 I3 I4 . 5_666 180.0
C5 N1 C1 . . 121.2(5)
C5 N1 C14 . . 119.2(5)
C1 N1 C14 . . 119.6(5)
C11 N2 C15 . . 121.2(5)
C11 N2 C16 . . 120.9(5)
C15 N2 C16 . . 117.9(5)
C2 C1 N1 . . 122.9(6)
C2 C1 H1A . . 118.6
N1 C1 H1A . . 118.6
C1 C2 C3 . . 118.4(6)
C1 C2 H2A . . 120.8
C3 C2 H2A . . 120.8
C4 C3 C2 . . 119.4(6)
C4 C3 H3A . . 120.3
C2 C3 H3A . . 120.3
C3 C4 C5 . . 121.3(5)
C3 C4 H4A . . 119.4
C5 C4 H4A . . 119.4
N1 C5 C6 . . 122.4(5)
N1 C5 C4 . . 116.8(5)
C6 C5 C4 . . 120.8(5)
C7 C6 C5 . . 127.2(5)
C7 C6 H6A . . 116.4
C5 C6 H6A . . 116.4
C6 C7 C8 . . 129.3(5)
C6 C7 H7A . . 115.4
C8 C7 H7A . . 115.4
C9 C8 C13 . . 117.6(5)
C9 C8 C7 . . 117.5(5)
C13 C8 C7 . . 124.9(5)
C10 C9 C8 . . 122.6(5)
C10 C9 H9A . . 118.7
C8 C9 H9A . . 118.7
C9 C10 C11 . . 121.7(5)
C9 C10 H10A . . 119.2
C11 C10 H10A . . 119.2
N2 C11 C10 . . 122.2(5)
N2 C11 C12 . . 120.6(5)
C10 C11 C12 . . 117.3(5)
C13 C12 C11 . . 120.1(5)
C13 C12 H12A . . 120.0
C11 C12 H12A . . 120.0
C12 C13 C8 . . 120.8(5)
C12 C13 H13A . . 119.6
C8 C13 H13A . . 119.6
N1 C14 H14A . . 106.9
N1 C14 H14B . . 112.4
H14A C14 H14B . . 111.7
N2 C15 H15A . . 107.3
N2 C15 H15B . . 111.7
H15A C15 H15B . . 111.7
N2 C16 H16A . . 107.2
N2 C16 H16B . . 111.9
H16A C16 H16B . . 111.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 I2 5_665 2.9054(4)
I1 I2 . 2.9054(4)
I3 I4 . 2.9347(4)
I3 I4 5_666 2.9347(4)
N1 C5 . 1.346(7)
N1 C1 . 1.375(7)
N1 C14 . 1.448(8)
N2 C11 . 1.373(7)
N2 C15 . 1.433(8)
N2 C16 . 1.476(9)
C1 C2 . 1.327(9)
C1 H1A . 0.9500
C2 C3 . 1.425(9)
C2 H2A . 0.9500
C3 C4 . 1.341(9)
C3 H3A . 0.9500
C4 C5 . 1.449(9)
C4 H4A . 0.9500
C5 C6 . 1.438(7)
C6 C7 . 1.327(8)
C6 H6A . 0.9500
C7 C8 . 1.459(8)
C7 H7A . 0.9500
C8 C9 . 1.389(8)
C8 C13 . 1.407(9)
C9 C10 . 1.339(8)
C9 H9A . 0.9500
C10 C11 . 1.407(7)
C10 H10A . 0.9500
C11 C12 . 1.420(7)
C12 C13 . 1.396(8)
C12 H12A . 0.9500
C13 H13A . 0.9500
C14 H14A . 0.9601
C14 H14B . 0.9600
C15 H15A . 0.9600
C15 H15B . 0.9598
C16 H16A . 0.9600
C16 H16B . 0.9600
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
C5 N1 C1 C2 0.000(3)
C14 N1 C1 C2 180.000(2)
N1 C1 C2 C3 0.000(3)
C1 C2 C3 C4 0.000(3)
C2 C3 C4 C5 0.000(3)
C1 N1 C5 C6 180.000(2)
C14 N1 C5 C6 0.000(3)
C1 N1 C5 C4 0.000(3)
C14 N1 C5 C4 180.000(2)
C3 C4 C5 N1 0.000(2)
C3 C4 C5 C6 180.000(2)
N1 C5 C6 C7 180.000(2)
C4 C5 C6 C7 0.000(3)
C5 C6 C7 C8 180.000(2)
C6 C7 C8 C9 180.000(2)
C6 C7 C8 C13 0.000(2)
C13 C8 C9 C10 0.000(2)
C7 C8 C9 C10 180.000(2)
C8 C9 C10 C11 0.000(2)
C15 N2 C11 C10 0.000(2)
C16 N2 C11 C10 180.0000(10)
C15 N2 C11 C12 180.0000(10)
C16 N2 C11 C12 0.000(2)
C9 C10 C11 N2 180.0000(10)
C9 C10 C11 C12 0.000(2)
N2 C11 C12 C13 180.000(2)
C10 C11 C12 C13 0.000(2)
C11 C12 C13 C8 0.000(2)
C9 C8 C13 C12 0.000(2)
C7 C8 C13 C12 180.000(2)
