#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223866.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_2223866
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
'Surasit, Chanasuk'
'Chanawanno, Kullapa'
_publ_section_title
;
(E)-1-Methyl-4-styrylpyridinium iodide monohydrate
;
_journal_coeditor_code IS2467
_journal_issue 11
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o2676
_journal_page_last o2677
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C14 H14 N +, I -, H2 O'
_chemical_formula_moiety 'C14 H14 N +, I -, H2 O'
_chemical_formula_sum 'C14 H16 I N O'
_chemical_formula_weight 341.18
_chemical_melting_point_gt 489
_chemical_melting_point_lt 490
_chemical_name_common
;
;
_chemical_name_systematic
;
(E)-1-Methyl-4-styrylpyridinium iodide monohydrate
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_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_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 106.7700(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.36360(10)
_cell_length_b 10.59290(10)
_cell_length_c 18.2807(2)
_cell_measurement_reflns_used 6004
_cell_measurement_temperature 100
_cell_measurement_theta_max 35.00
_cell_measurement_theta_min 2.25
_cell_volume 1365.29(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEXII CCD area-detector'
_diffrn_measurement_method '\f and \w'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0208
_diffrn_reflns_av_sigmaI/netI 0.0186
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_number 27548
_diffrn_reflns_theta_full 35.00
_diffrn_reflns_theta_max 35.00
_diffrn_reflns_theta_min 2.25
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 2.330
_exptl_absorpt_correction_T_max 0.6491
_exptl_absorpt_correction_T_min 0.5236
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_crystal_colour Yellow
_exptl_crystal_density_diffrn 1.660
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 672
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_refine_diff_density_max 1.319
_refine_diff_density_min -0.558
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 163
_refine_ls_number_reflns 6004
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.046
_refine_ls_R_factor_all 0.0286
_refine_ls_R_factor_gt 0.0233
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+0.8184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0553
_refine_ls_wR_factor_ref 0.0578
_reflns_number_gt 5307
_reflns_number_total 6004
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file is2467.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_database_code 2223866
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
I I1 0.742589(15) 0.831113(9) 0.885210(5) 0.02548(3) Uani d . 1
O O1W 0.20711(19) 0.98174(12) 0.94686(7) 0.0308(2) Uani d . 1
H H1W1 0.086(4) 0.944(3) 0.9327(16) 0.060(8) Uiso d . 1
H H2W1 0.210(4) 1.028(2) 0.9901(15) 0.048(7) Uiso d . 1
N N1 0.53960(16) 0.74866(11) 1.12888(6) 0.01776(19) Uani d . 1
C C1 0.3622(2) 0.68934(13) 1.00380(8) 0.0219(2) Uani d . 1
H H1A 0.3146 0.7096 0.9523 0.026 Uiso calc R 1
C C2 0.4699(2) 0.77624(13) 1.05393(8) 0.0218(2) Uani d . 1
H H2A 0.4948 0.8546 1.0360 0.026 Uiso calc R 1
C C3 0.5064(2) 0.63509(12) 1.15607(7) 0.0185(2) Uani d . 1
H H3A 0.5556 0.6174 1.2079 0.022 Uiso calc R 1
C C4 0.4006(2) 0.54563(12) 1.10806(7) 0.0187(2) Uani d . 1
H H4A 0.3796 0.4676 1.1275 0.022 Uiso calc R 1
C C5 0.32393(19) 0.57076(12) 1.02979(7) 0.0176(2) Uani d . 1
C C6 0.2111(2) 0.47325(12) 0.98062(7) 0.0191(2) Uani d . 1
H H6A 0.1960 0.3967 1.0031 0.023 Uiso calc R 1
C C7 0.12773(19) 0.48617(12) 0.90531(7) 0.0188(2) Uani d . 1
H H7A 0.1434 0.5629 0.8832 0.023 Uiso calc R 1
C C8 0.01415(19) 0.38969(12) 0.85514(7) 0.0175(2) Uani d . 1
C C9 -0.0249(2) 0.27106(12) 0.88126(8) 0.0195(2) Uani d . 1
H H9A 0.0259 0.2496 0.9324 0.023 Uiso calc R 1
C C10 -0.1394(2) 0.18542(12) 0.83081(9) 0.0214(2) Uani d . 1
H H10A -0.1634 0.1065 0.8482 0.026 Uiso calc R 1
C C11 -0.2182(2) 0.21752(13) 0.75423(8) 0.0214(2) Uani d . 1
H H11A -0.2975 0.1609 0.7210 0.026 Uiso calc R 1
C C12 -0.1783(2) 0.33396(13) 0.72750(8) 0.0226(2) Uani d . 1
H H12A -0.2297 0.3551 0.6763 0.027 Uiso calc R 1
C C13 -0.0616(2) 0.41849(13) 0.77750(8) 0.0206(2) Uani d . 1
H H13A -0.0331 0.4956 0.7592 0.025 Uiso calc R 1
C C14 0.6473(2) 0.84639(13) 1.18135(8) 0.0234(3) Uani d . 1
H H14A 0.7349 0.8866 1.1588 0.035 Uiso calc R 1
H H14B 0.7160 0.8079 1.2288 0.035 Uiso calc R 1
H H14C 0.5611 0.9082 1.1906 0.035 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.03493(6) 0.02076(4) 0.01682(4) -0.00883(3) 0.00120(3) 0.00305(3)
O1W 0.0324(6) 0.0315(6) 0.0294(5) 0.0025(5) 0.0103(5) -0.0004(4)
N1 0.0178(5) 0.0184(4) 0.0172(4) -0.0012(4) 0.0054(4) -0.0003(3)
C1 0.0249(7) 0.0220(6) 0.0176(5) -0.0017(5) 0.0043(5) 0.0029(4)
C2 0.0247(7) 0.0209(6) 0.0199(5) -0.0022(5) 0.0065(5) 0.0038(4)
C3 0.0203(6) 0.0177(5) 0.0183(5) 0.0011(4) 0.0068(4) 0.0015(4)
C4 0.0207(6) 0.0174(5) 0.0191(5) 0.0005(4) 0.0074(4) 0.0018(4)
C5 0.0166(5) 0.0181(5) 0.0182(5) 0.0008(4) 0.0055(4) 0.0011(4)
C6 0.0202(6) 0.0177(5) 0.0194(5) 0.0002(4) 0.0060(4) 0.0017(4)
C7 0.0193(6) 0.0181(5) 0.0192(5) 0.0008(4) 0.0058(4) 0.0025(4)
C8 0.0159(5) 0.0178(5) 0.0188(5) 0.0006(4) 0.0051(4) 0.0005(4)
C9 0.0186(6) 0.0181(5) 0.0212(5) 0.0024(4) 0.0049(4) 0.0033(4)
C10 0.0207(6) 0.0158(5) 0.0281(6) 0.0012(4) 0.0077(5) 0.0023(4)
C11 0.0198(6) 0.0208(6) 0.0238(6) -0.0012(5) 0.0068(5) -0.0047(4)
C12 0.0243(7) 0.0251(6) 0.0178(5) -0.0005(5) 0.0054(5) 0.0005(4)
C13 0.0212(6) 0.0207(5) 0.0200(5) -0.0015(5) 0.0064(5) 0.0026(4)
C14 0.0248(7) 0.0228(6) 0.0224(6) -0.0050(5) 0.0065(5) -0.0044(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
H1W1 O1W H2W1 104(2)
C2 N1 C3 120.69(12)
C2 N1 C14 118.90(12)
C3 N1 C14 120.37(11)
C2 C1 C5 120.49(12)
C2 C1 H1A 119.8
C5 C1 H1A 119.8
N1 C2 C1 120.55(12)
N1 C2 H2A 119.7
C1 C2 H2A 119.7
N1 C3 C4 120.65(12)
N1 C3 H3A 119.7
C4 C3 H3A 119.7
C3 C4 C5 120.56(12)
C3 C4 H4A 119.7
C5 C4 H4A 119.7
C1 C5 C4 117.05(12)
C1 C5 C6 124.05(12)
C4 C5 C6 118.90(12)
C7 C6 C5 124.71(12)
C7 C6 H6A 117.6
C5 C6 H6A 117.6
C6 C7 C8 125.51(12)
C6 C7 H7A 117.2
C8 C7 H7A 117.2
C13 C8 C9 118.63(12)
C13 C8 C7 118.12(12)
C9 C8 C7 123.24(11)
C10 C9 C8 120.19(12)
C10 C9 H9A 119.9
C8 C9 H9A 119.9
C9 C10 C11 120.24(12)
C9 C10 H10A 119.9
C11 C10 H10A 119.9
C12 C11 C10 120.06(13)
C12 C11 H11A 120.0
C10 C11 H11A 120.0
C13 C12 C11 119.69(13)
C13 C12 H12A 120.2
C11 C12 H12A 120.2
C12 C13 C8 121.14(12)
C12 C13 H13A 119.4
C8 C13 H13A 119.4
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1W H1W1 0.94(3)
O1W H2W1 0.93(3)
N1 C2 1.3491(17)
N1 C3 1.3507(17)
N1 C14 1.4772(18)
C1 C2 1.377(2)
C1 C5 1.4003(19)
C1 H1A 0.9300
C2 H2A 0.9300
C3 C4 1.3711(19)
C3 H3A 0.9300
C4 C5 1.4039(18)
C4 H4A 0.9300
C5 C6 1.4608(19)
C6 C7 1.3429(18)
C6 H6A 0.9300
C7 C8 1.4637(18)
C7 H7A 0.9300
C8 C13 1.4005(18)
C8 C9 1.4032(19)
C9 C10 1.391(2)
C9 H9A 0.9300
C10 C11 1.394(2)
C10 H10A 0.9300
C11 C12 1.389(2)
C11 H11A 0.9300
C12 C13 1.387(2)
C12 H12A 0.9300
C13 H13A 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
O1W H1W1 I1 1_455 0.94(3) 2.70(3) 3.6458(14) 177(3) y
O1W H2W1 I1 3_677 0.93(3) 2.66(2) 3.5826(12) 174(2) y
C14 H14A O1W 3_677 0.96 2.52 3.3775(19) 149 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
C3 N1 C2 C1 0.5(2)
C14 N1 C2 C1 -177.34(14)
C5 C1 C2 N1 -0.2(2)
C2 N1 C3 C4 -0.2(2)
C14 N1 C3 C4 177.64(13)
N1 C3 C4 C5 -0.4(2)
C2 C1 C5 C4 -0.3(2)
C2 C1 C5 C6 179.97(14)
C3 C4 C5 C1 0.7(2)
C3 C4 C5 C6 -179.63(13)
C1 C5 C6 C7 -1.4(2)
C4 C5 C6 C7 178.88(14)
C5 C6 C7 C8 -179.95(13)
C6 C7 C8 C13 -179.47(14)
C6 C7 C8 C9 1.6(2)
C13 C8 C9 C10 -1.1(2)
C7 C8 C9 C10 177.78(13)
C8 C9 C10 C11 -0.9(2)
C9 C10 C11 C12 1.8(2)
C10 C11 C12 C13 -0.7(2)
C11 C12 C13 C8 -1.3(2)
C9 C8 C13 C12 2.2(2)
C7 C8 C13 C12 -176.72(13)