#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228415.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228415
loop_
_publ_author_name
'Mueangkeaw, Charoensak'
'Chantrapromma, Suchada'
'Ruanwas, Pumsak'
'Fun, Hoong-Kun'
_publ_section_title
;
 1-Methyl-2-[(E)-2,4,5-trimethoxystyryl]pyridinium iodide
;
_journal_coeditor_code           IS2612
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3098
_journal_page_last               o3099
_journal_paper_doi               10.1107/S1600536810043254
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H20 N O3 +, I -'
_chemical_formula_moiety         'C17 H20 N O3 +, I -'
_chemical_formula_sum            'C17 H20 I N O3'
_chemical_formula_weight         413.24
_chemical_melting_point_gt       544
_chemical_melting_point_lt       545
_chemical_name_systematic
;
1-Methyl-2-[(E)-2,4,5-trimethoxystyryl]pyridinium iodide
;
_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                113.3820(10)
_cell_angle_beta                 109.2430(10)
_cell_angle_gamma                96.8310(10)
_cell_formula_units_Z            2
_cell_length_a                   8.91090(10)
_cell_length_b                   10.35510(10)
_cell_length_c                   10.8201(2)
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.24
_cell_volume                     828.51(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29408
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.944
_exptl_absorpt_correction_T_max  0.7198
_exptl_absorpt_correction_T_min  0.5339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.853
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0275
_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)+(0.0418P)²+1.7349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                4686
_reflns_number_total             4827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2612.cif
_cod_data_source_block           I
_cod_database_code               2228415
_cod_database_fobs_code          2228415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
I I1 0.63632(2) 0.272468(17) 0.263674(17) 0.01981(6) Uani d . 1 . .
O O1 0.1870(2) 0.19738(18) 0.43228(18) 0.0142(3) Uani d . 1 . .
O O2 0.0422(2) 0.40374(18) 0.85063(19) 0.0141(3) Uani d . 1 . .
O O3 0.1169(2) 0.20276(19) 0.92393(19) 0.0152(3) Uani d . 1 . .
N N1 0.3476(2) -0.2139(2) 0.1812(2) 0.0116(3) Uani d . 1 . .
C C1 0.3923(3) -0.3317(3) 0.1060(3) 0.0164(4) Uani d . 1 . .
H H1A 0.3941 -0.3480 0.0156 0.020 Uiso calc R 1 . .
C C2 0.4348(3) -0.4269(3) 0.1614(3) 0.0179(4) Uani d . 1 . .
H H2A 0.4628 -0.5085 0.1084 0.022 Uiso calc R 1 . .
C C3 0.4351(3) -0.3990(3) 0.2983(3) 0.0157(4) Uani d . 1 . .
H H3A 0.4656 -0.4611 0.3387 0.019 Uiso calc R 1 . .
C C4 0.3902(3) -0.2792(2) 0.3738(2) 0.0133(4) Uani d . 1 . .
H H4A 0.3916 -0.2604 0.4657 0.016 Uiso calc R 1 . .
C C5 0.3422(3) -0.1847(2) 0.3140(2) 0.0105(3) Uani d . 1 . .
C C6 0.2895(3) -0.0589(2) 0.3851(2) 0.0118(4) Uani d . 1 . .
H H6A 0.2727 0.0048 0.3442 0.014 Uiso calc R 1 . .
C C7 0.2639(3) -0.0305(2) 0.5083(2) 0.0109(3) Uani d . 1 . .
H H7A 0.2832 -0.0967 0.5456 0.013 Uiso calc R 1 . .
C C8 0.2103(3) 0.0895(2) 0.5905(2) 0.0101(3) Uani d . 1 . .
C C9 0.1697(3) 0.2006(2) 0.5538(2) 0.0109(4) Uani d . 1 . .
C C10 0.1146(3) 0.3083(2) 0.6399(2) 0.0117(4) Uani d . 1 . .
H H10A 0.0887 0.3814 0.6148 0.014 Uiso calc R 1 . .
C C11 0.0984(3) 0.3064(2) 0.7627(2) 0.0111(4) Uani d . 1 . .
C C12 0.1396(3) 0.1966(2) 0.8021(2) 0.0116(4) Uani d . 1 . .
C C13 0.1940(3) 0.0915(2) 0.7170(2) 0.0112(4) Uani d . 1 . .
H H13A 0.2210 0.0193 0.7435 0.013 Uiso calc R 1 . .
C C14 0.3022(3) -0.1177(3) 0.1125(3) 0.0177(4) Uani d . 1 . .
H H14A 0.3121 -0.1545 0.0198 0.027 Uiso calc R 1 . .
H H14B 0.3754 -0.0198 0.1771 0.027 Uiso calc R 1 . .
H H14C 0.1899 -0.1165 0.0960 0.027 Uiso calc R 1 . .
C C15 0.1497(3) 0.3104(3) 0.3933(3) 0.0196(5) Uani d . 1 . .
H H15A 0.1785 0.3010 0.3127 0.029 Uiso calc R 1 . .
H H15B 0.2124 0.4049 0.4769 0.029 Uiso calc R 1 . .
H H15C 0.0333 0.3012 0.3641 0.029 Uiso calc R 1 . .
C C16 0.0013(3) 0.5189(3) 0.8167(3) 0.0163(4) Uani d . 1 . .
H H16A -0.0356 0.5804 0.8869 0.024 Uiso calc R 1 . .
H H16B -0.0855 0.4769 0.7189 0.024 Uiso calc R 1 . .
H H16C 0.0977 0.5766 0.8214 0.024 Uiso calc R 1 . .
C C17 0.1636(3) 0.0946(3) 0.9660(3) 0.0197(4) Uani d . 1 . .
H H17A 0.1415 0.1061 1.0503 0.030 Uiso calc R 1 . .
H H17B 0.2798 0.1062 0.9907 0.030 Uiso calc R 1 . .
H H17C 0.1008 -0.0016 0.8853 0.030 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C9 O1 C15 . . 118.29(17) ?
C11 O2 C16 . . 117.54(18) ?
C12 O3 C17 . . 115.34(17) ?
C1 N1 C5 . . 122.11(19) ?
C1 N1 C14 . . 117.39(19) ?
C5 N1 C14 . . 120.50(18) ?
N1 C1 C2 . . 121.0(2) ?
N1 C1 H1A . . 119.5 ?
C2 C1 H1A . . 119.5 ?
C1 C2 C3 . . 118.8(2) ?
C1 C2 H2A . . 120.6 ?
C3 C2 H2A . . 120.6 ?
C4 C3 C2 . . 119.8(2) ?
C4 C3 H3A . . 120.1 ?
C2 C3 H3A . . 120.1 ?
C3 C4 C5 . . 121.0(2) ?
C3 C4 H4A . . 119.5 ?
C5 C4 H4A . . 119.5 ?
N1 C5 C4 . . 117.30(19) ?
N1 C5 C6 . . 118.57(19) ?
C4 C5 C6 . . 124.13(19) ?
C7 C6 C5 . . 122.6(2) ?
C7 C6 H6A . . 118.7 ?
C5 C6 H6A . . 118.7 ?
C6 C7 C8 . . 128.7(2) ?
C6 C7 H7A . . 115.6 ?
C8 C7 H7A . . 115.6 ?
C9 C8 C13 . . 117.62(18) ?
C9 C8 C7 . . 126.06(19) ?
C13 C8 C7 . . 116.29(18) ?
O1 C9 C10 . . 122.56(19) ?
O1 C9 C8 . . 116.78(18) ?
C10 C9 C8 . . 120.65(19) ?
C11 C10 C9 . . 120.37(19) ?
C11 C10 H10A . . 119.8 ?
C9 C10 H10A . . 119.8 ?
O2 C11 C10 . . 124.67(19) ?
O2 C11 C12 . . 115.43(18) ?
C10 C11 C12 . . 119.89(19) ?
C13 C12 O3 . . 125.15(19) ?
C13 C12 C11 . . 119.29(19) ?
O3 C12 C11 . . 115.53(18) ?
C12 C13 C8 . . 122.16(19) ?
C12 C13 H13A . . 118.9 ?
C8 C13 H13A . . 118.9 ?
N1 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O2 C16 H16A . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 C17 H17A . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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
O1 C9 . 1.362(2) ?
O1 C15 . 1.432(3) ?
O2 C11 . 1.358(2) ?
O2 C16 . 1.433(3) ?
O3 C12 . 1.377(3) ?
O3 C17 . 1.423(3) ?
N1 C1 . 1.360(3) ?
N1 C5 . 1.366(3) ?
N1 C14 . 1.481(3) ?
C1 C2 . 1.372(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.391(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.378(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.406(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.448(3) ?
C6 C7 . 1.350(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.451(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.407(3) ?
C8 C13 . 1.416(3) ?
C9 C10 . 1.399(3) ?
C10 C11 . 1.391(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.411(3) ?
C12 C13 . 1.375(3) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6A O1 1_555 0.93 2.19 2.819(3) 124 y
C14 H14A I1 2_655 0.96 3.03 3.992(3) 177 y
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
C5 N1 C1 C2 . . . . -0.2(3) ?
C14 N1 C1 C2 . . . . -179.5(2) ?
N1 C1 C2 C3 . . . . -1.5(4) ?
C1 C2 C3 C4 . . . . 1.3(4) ?
C2 C3 C4 C5 . . . . 0.6(4) ?
C1 N1 C5 C4 . . . . 2.0(3) ?
C14 N1 C5 C4 . . . . -178.8(2) ?
C1 N1 C5 C6 . . . . -178.5(2) ?
C14 N1 C5 C6 . . . . 0.6(3) ?
C3 C4 C5 N1 . . . . -2.2(3) ?
C3 C4 C5 C6 . . . . 178.4(2) ?
N1 C5 C6 C7 . . . . 173.0(2) ?
C4 C5 C6 C7 . . . . -7.7(3) ?
C5 C6 C7 C8 . . . . -179.5(2) ?
C6 C7 C8 C9 . . . . 1.7(4) ?
C6 C7 C8 C13 . . . . -179.9(2) ?
C15 O1 C9 C10 . . . . 1.0(3) ?
C15 O1 C9 C8 . . . . -178.9(2) ?
C13 C8 C9 O1 . . . . 179.63(19) ?
C7 C8 C9 O1 . . . . -2.0(3) ?
C13 C8 C9 C10 . . . . -0.3(3) ?
C7 C8 C9 C10 . . . . 178.1(2) ?
O1 C9 C10 C11 . . . . 179.8(2) ?
C8 C9 C10 C11 . . . . -0.3(3) ?
C16 O2 C11 C10 . . . . -1.9(3) ?
C16 O2 C11 C12 . . . . 178.99(19) ?
C9 C10 C11 O2 . . . . -178.3(2) ?
C9 C10 C11 C12 . . . . 0.8(3) ?
C17 O3 C12 C13 . . . . 3.6(3) ?
C17 O3 C12 C11 . . . . -178.1(2) ?
O2 C11 C12 C13 . . . . 178.53(19) ?
C10 C11 C12 C13 . . . . -0.6(3) ?
O2 C11 C12 O3 . . . . 0.1(3) ?
C10 C11 C12 O3 . . . . -179.03(19) ?
O3 C12 C13 C8 . . . . 178.2(2) ?
C11 C12 C13 C8 . . . . 0.0(3) ?
C9 C8 C13 C12 . . . . 0.4(3) ?
C7 C8 C13 C12 . . . . -178.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656367
