#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/30/2213030.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_2213030
loop_
_publ_author_name
'Maksymilian Chruszcz'
'Yali Kong'
'Zbigniew Dauter'
'Milton Brown'
'Wladek Minor'
_publ_section_title
;
 2-Amino-4-(4-chloro-3-methylphenyl)-5-propyl-1,3-thiazolium iodide
;
_journal_coeditor_code           SQ3066
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1598
_journal_page_last               o1600
_journal_paper_doi               10.1107/S1600536807009427
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H16 Cl N2 S +, I -'
_chemical_formula_moiety         'C13 H16 Cl N2 S +, I -'
_chemical_formula_sum            'C13 H16 Cl I N2 S'
_chemical_formula_weight         394.69
_chemical_name_systematic
;
2-Amino-4-(4-chloro-3-methylphenyl)-5-propyl-1,3-thiazolium iodide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                sm
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method
'HKL2000-CIF automatic completion and interactive editing'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7610(10)
_cell_length_b                   9.6590(10)
_cell_length_c                   20.1450(10)
_cell_measurement_reflns_used    107797
_cell_measurement_temperature    103
_cell_measurement_theta_max      52.3
_cell_measurement_theta_min      2.3
_cell_volume                     1510.1(3)
_computing_cell_refinement       HKL-2000
_computing_data_collection       'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        HKL-2000
_computing_molecular_graphics
;
HKL-3000SM,
ORTEPIII (Burnett & Johnson, 1996),
ORTEP-3 (Farrugia, 1997) and
MERCURY (Macrae et al.,  2006)
;
_computing_publication_material  HKL-3000SM
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 1997) and
HKL-3000SM
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 1990) and
HKL-3000SM (Minor et al.,  2006)
;
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans with χ offset'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71074
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            107797
_diffrn_reflns_reduction_process
;
 data merged using denzo and scalepack by evaluating a new profile for each
 reflection based on spots lying within a pre-specified radius
;
_diffrn_reflns_theta_full        52.28
_diffrn_reflns_theta_max         52.3
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Otwinowski et al.,  2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.236
_refine_diff_density_min         -0.980
_refine_ls_abs_structure_details 'Flack (1983), 7019 Friedel pairs?'
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_coef       0.0111(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         16517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0474P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                14434
_reflns_number_observed          16560
_reflns_number_total             16521
_reflns_observed_criterion       >-3sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sq3066.cif
_cod_data_source_block           I
_cod_database_code               2213030
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
I I1 0.435396(9) 0.147814(6) 0.129970(3) 0.02266(2) Uani d . 1
S S1 0.66083(3) 0.59544(2) 0.176000(11) 0.02010(4) Uani d . 1
Cl Cl1 0.68767(4) 0.90064(3) -0.220879(12) 0.02924(5) Uani d . 1
C C7 0.61921(12) 0.66781(9) -0.05937(4) 0.01859(11) Uani d . 1
H H7 0.5837 0.5784 -0.0490 0.022 Uiso calc R 1
N N1 0.60319(11) 0.81119(8) 0.10852(3) 0.01909(11) Uani d . 1
C C5 0.69493(12) 0.58856(9) 0.08993(4) 0.01833(11) Uani d . 1
C C6 0.66899(11) 0.75651(9) -0.00818(4) 0.01716(10) Uani d . 1
C C4 0.65752(11) 0.71285(8) 0.06174(4) 0.01732(11) Uani d . 1
C C9 0.68185(12) 0.84269(10) -0.13947(4) 0.02040(12) Uani d . 1
C C12 0.75770(13) 0.45677(9) 0.05918(5) 0.02171(13) Uani d . 1
H H12A 0.8290 0.4793 0.0211 0.026 Uiso calc R 1
H H12B 0.6592 0.4047 0.0432 0.026 Uiso calc R 1
C C2 0.59492(12) 0.76502(9) 0.17101(4) 0.01943(12) Uani d . 1
N N2 0.54162(15) 0.84122(9) 0.22153(4) 0.02564(15) Uani d . 1
C C8 0.62112(12) 0.70931(9) -0.12589(4) 0.01944(11) Uani d . 1
C C13 0.86102(13) 0.36576(10) 0.10630(5) 0.02203(13) Uani d . 1
H H13A 0.7871 0.3348 0.1422 0.026 Uiso calc R 1
H H13B 0.9540 0.4196 0.1255 0.026 Uiso calc R 1
C C15 0.55685(17) 0.61508(12) -0.17990(5) 0.02696(17) Uani d . 1
H H15A 0.5209 0.5287 -0.1609 0.040 Uiso calc PR 0.50
H H15B 0.6476 0.5987 -0.2113 0.040 Uiso calc PR 0.50
H H15C 0.4610 0.6577 -0.2020 0.040 Uiso calc PR 0.50
H H15D 0.5655 0.6614 -0.2219 0.040 Uiso calc PR 0.50
H H15E 0.4387 0.5914 -0.1715 0.040 Uiso calc PR 0.50
H H15F 0.6253 0.5323 -0.1808 0.040 Uiso calc PR 0.50
C C11 0.72521(12) 0.89064(9) -0.02353(4) 0.01973(12) Uani d . 1
H H11 0.7564 0.9511 0.0103 0.024 Uiso calc R 1
C C14 0.9360(2) 0.24007(13) 0.07063(7) 0.0350(2) Uani d . 1
H H14A 1.0002 0.1849 0.1016 0.052 Uiso calc PR 0.50
H H14B 1.0108 0.2705 0.0356 0.052 Uiso calc PR 0.50
H H14C 0.8440 0.1857 0.0522 0.052 Uiso calc PR 0.50
H H14D 0.9032 0.2425 0.0247 0.052 Uiso calc PR 0.50
H H14E 0.8925 0.1569 0.0907 0.052 Uiso calc PR 0.50
H H14F 1.0593 0.2417 0.0741 0.052 Uiso calc PR 0.50
C C10 0.73433(13) 0.93341(10) -0.08942(5) 0.02122(13) Uani d . 1
H H10 0.7749 1.0213 -0.1000 0.025 Uiso calc R 1
H H1 0.560(2) 0.888(2) 0.0987(9) 0.022(4) Uiso d . 1
H H2 0.509(3) 0.917(2) 0.2157(9) 0.025(4) Uiso d . 1
H H3 0.563(2) 0.815(3) 0.2619(10) 0.034(5) Uiso d . 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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C2 S1 C5 91.33(4) yes
C6 C7 C8 121.95(8) ?
C6 C7 H7 119.0 ?
C8 C7 H7 119.0 ?
C2 N1 C4 114.90(7) ?
C2 N1 H1 119.9(12) ?
C4 N1 H1 124.1(12) ?
C4 C5 C12 130.36(7) ?
C4 C5 S1 110.30(6) yes
C12 C5 S1 119.34(6) yes
C7 C6 C11 119.39(7) ?
C7 C6 C4 120.94(7) ?
C11 C6 C4 119.63(7) ?
C5 C4 N1 112.43(7) yes
C5 C4 C6 129.74(7) yes
N1 C4 C6 117.82(7) yes
C10 C9 C8 122.34(7) ?
C10 C9 Cl1 118.22(7) ?
C8 C9 Cl1 119.42(7) ?
C5 C12 C13 113.85(8) ?
C5 C12 H12A 108.8 ?
C13 C12 H12A 108.8 ?
C5 C12 H12B 108.8 ?
C13 C12 H12B 108.8 ?
H12A C12 H12B 107.7 ?
N2 C2 N1 123.64(8) yes
N2 C2 S1 125.34(7) yes
N1 C2 S1 111.02(6) yes
C2 N2 H2 120.3(14) ?
C2 N2 H3 119.9(16) ?
H2 N2 H3 118(2) ?
C9 C8 C7 117.06(8) ?
C9 C8 C15 121.85(8) ?
C7 C8 C15 121.08(9) ?
C12 C13 C14 111.50(9) ?
C12 C13 H13A 109.3 ?
C14 C13 H13A 109.3 ?
C12 C13 H13B 109.3 ?
C14 C13 H13B 109.3 ?
H13A C13 H13B 108.0 ?
C8 C15 H15A 109.5 ?
C8 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C8 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C8 C15 H15D 109.5 ?
H15A C15 H15D 141.1 ?
H15B C15 H15D 56.3 ?
H15C C15 H15D 56.3 ?
C8 C15 H15E 109.5 ?
H15A C15 H15E 56.3 ?
H15B C15 H15E 141.1 ?
H15C C15 H15E 56.3 ?
H15D C15 H15E 109.5 ?
C8 C15 H15F 109.5 ?
H15A C15 H15F 56.3 ?
H15B C15 H15F 56.3 ?
H15C C15 H15F 141.1 ?
H15D C15 H15F 109.5 ?
H15E C15 H15F 109.5 ?
C10 C11 C6 120.04(8) ?
C10 C11 H11 120.0 ?
C6 C11 H11 120.0 ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C13 C14 H14D 109.5 ?
H14A C14 H14D 141.1 ?
H14B C14 H14D 56.3 ?
H14C C14 H14D 56.3 ?
C13 C14 H14E 109.5 ?
H14A C14 H14E 56.3 ?
H14B C14 H14E 141.1 ?
H14C C14 H14E 56.3 ?
H14D C14 H14E 109.5 ?
C13 C14 H14F 109.5 ?
H14A C14 H14F 56.3 ?
H14B C14 H14F 56.3 ?
H14C C14 H14F 141.1 ?
H14D C14 H14F 109.5 ?
H14E C14 H14F 109.5 ?
C11 C10 C9 119.17(8) ?
C11 C10 H10 120.4 ?
C9 C10 H10 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.7190(10) yes
S1 C5 1.7550(10) yes
Cl1 C9 1.7330(10) ?
C7 C6 1.3950(10) ?
C7 C8 1.3990(10) ?
C7 H7 0.9300 ?
N1 C2 1.3370(10) yes
N1 C4 1.4030(10) yes
N1 H1 0.835(19) ?
C5 C4 1.3590(10) yes
C5 C12 1.4971(12) ?
C6 C11 1.4016(12) ?
C6 C4 1.4730(10) yes
C9 C10 1.3965(14) ?
C9 C8 1.3989(13) ?
C12 C13 1.5222(13) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C2 N2 1.3220(10) yes
N2 H2 0.78(2) ?
N2 H3 0.87(2) ?
C8 C15 1.5037(13) ?
C13 C14 1.5260(15) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C15 H15D 0.9600 ?
C15 H15E 0.9600 ?
C15 H15F 0.9600 ?
C11 C10 1.3919(12) ?
C11 H11 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C14 H14D 0.9600 ?
C14 H14E 0.9600 ?
C14 H14F 0.9600 ?
C10 H10 0.9300 ?
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
N1 H1 I1 1_565 0.84(2) 2.77(2) 3.5290(10) 153(2)
N2 H2 I1 1_565 0.78(2) 2.88(2) 3.5850(10) 152(2)
N2 H3 I1 3_655 0.87(2) 2.71(2) 3.5310(10) 158(2)
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
_geom_torsion_publ_flag
C2 S1 C5 C4 0.65(8) ?
C2 S1 C5 C12 -179.66(8) ?
C8 C7 C6 C11 -0.98(14) ?
C8 C7 C6 C4 176.87(8) ?
C12 C5 C4 N1 -179.48(10) ?
S1 C5 C4 N1 0.16(10) ?
C12 C5 C4 C6 -0.64(17) ?
S1 C5 C4 C6 179.01(8) ?
C2 N1 C4 C5 -1.23(12) ?
C2 N1 C4 C6 179.78(8) ?
C7 C6 C4 C5 40.30(10) yes
C11 C6 C4 C5 -141.90(10) yes
C7 C6 C4 N1 -141.00(10) yes
C11 C6 C4 N1 36.90(10) yes
C4 C5 C12 C13 153.03(10) ?
S1 C5 C12 C13 -26.59(12) ?
C4 N1 C2 N2 -177.89(10) ?
C4 N1 C2 S1 1.71(11) ?
C5 S1 C2 N2 178.26(10) ?
C5 S1 C2 N1 -1.33(8) ?
C10 C9 C8 C7 -1.75(13) ?
Cl1 C9 C8 C7 179.99(7) ?
C10 C9 C8 C15 176.96(10) ?
Cl1 C9 C8 C15 -1.30(12) ?
C6 C7 C8 C9 2.45(14) ?
C6 C7 C8 C15 -176.26(9) ?
C5 C12 C13 C14 -174.56(10) ?
C7 C6 C11 C10 -1.29(14) ?
C4 C6 C11 C10 -179.17(8) ?
C6 C11 C10 C9 1.97(14) ?
C8 C9 C10 C11 -0.43(14) ?
Cl1 C9 C10 C11 177.85(7) ?
