#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008176.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_2008176
loop_
_publ_author_name
'Clark, George R.'
'Denny, William A.'
'Squire, Christopher J.'
_publ_section_title
;
 1,4-Bis[4-(1-pyridinium)styryl]benzene ditosylate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              230
_journal_page_last               232
_journal_paper_doi               10.1107/S0108270198012396
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C32 H26 N2 2+, 2C7 H7 O3 S1 1-'
_chemical_formula_sum            'C46 H40 N2 O6 S2'
_chemical_formula_weight         780.92
_chemical_name_common            'SN 18071.Ts'
_chemical_name_systematic
;
 1,4-bis[4-(1-pyridinium)styryl)]benzene ditosylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                92.4180(10)
_cell_angle_beta                 99.6870(10)
_cell_angle_gamma                112.6660(10)
_cell_formula_units_Z            1
_cell_length_a                   7.2454(3)
_cell_length_b                   9.1927(4)
_cell_length_c                   15.6539(7)
_cell_measurement_reflns_used    6184
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      1.33
_cell_volume                     941.79(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1994b)'
_computing_data_reduction        'SHELXTL (Siemens, 1994a)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.888
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9218
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.33
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             410
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.040
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0517P)²+0.4359P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                3383
_reflns_number_total             4146
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1035.cif
_cod_data_source_block           os1035
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4359P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4359P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2008176
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
N1 0.2756(2) 0.27993(17) 0.37948(9) 0.0303(3) Uani d . 1 . . N
C2 0.3025(3) 0.1861(2) 0.44104(12) 0.0345(4) Uani d . 1 . . C
H2 0.185(3) 0.094(3) 0.4440(13) 0.041 Uiso d . 1 . . H
C3 0.4900(3) 0.2288(2) 0.49474(13) 0.0383(4) Uani d . 1 . . C
H3 0.505(3) 0.162(3) 0.5372(15) 0.046 Uiso d . 1 . . H
C4 0.6519(3) 0.3643(2) 0.48406(13) 0.0395(4) Uani d . 1 . . C
H4 0.782(3) 0.394(3) 0.5197(15) 0.047 Uiso d . 1 . . H
C5 0.6224(3) 0.4568(2) 0.42008(12) 0.0385(4) Uani d . 1 . . C
H5 0.728(3) 0.552(3) 0.4136(14) 0.046 Uiso d . 1 . . H
C6 0.4324(3) 0.4139(2) 0.36875(12) 0.0353(4) Uani d . 1 . . C
H6 0.396(3) 0.477(2) 0.3266(14) 0.042 Uiso d . 1 . . H
C7 0.0750(3) 0.2371(2) 0.32508(11) 0.0313(4) Uani d . 1 . . C
C8 0.0564(3) 0.2388(2) 0.23575(12) 0.0372(4) Uani d . 1 . . C
H8 0.171(3) 0.266(3) 0.2114(14) 0.045 Uiso d . 1 . . H
C9 -0.1370(3) 0.1962(2) 0.18469(13) 0.0396(4) Uani d . 1 . . C
H9 -0.136(3) 0.197(3) 0.1259(15) 0.048 Uiso d . 1 . . H
C10 -0.3099(3) 0.1504(2) 0.22228(12) 0.0354(4) Uani d . 1 . . C
C11 -0.2841(3) 0.1510(2) 0.31212(13) 0.0374(4) Uani d . 1 . . C
H11 -0.411(3) 0.118(2) 0.3371(14) 0.045 Uiso d . 1 . . H
C12 -0.0927(3) 0.1946(2) 0.36438(13) 0.0359(4) Uani d . 1 . . C
H12 -0.076(3) 0.197(2) 0.4301(15) 0.043 Uiso d . 1 . . H
C13 -0.5207(3) 0.0981(2) 0.17219(13) 0.0382(4) Uani d . 1 . . C
H13 -0.633(3) 0.055(2) 0.2045(14) 0.046 Uiso d . 1 . . H
C14 -0.5797(3) 0.1014(2) 0.08801(13) 0.0393(4) Uani d . 1 . . C
H14 -0.467(3) 0.148(3) 0.0522(14) 0.047 Uiso d . 1 . . H
C15 -0.7957(3) 0.0460(2) 0.04398(12) 0.0340(4) Uani d . 1 . . C
C16 -0.9572(3) -0.0563(2) 0.07792(13) 0.0400(4) Uani d . 1 . . C
H16 -0.928(3) -0.095(3) 0.1294(15) 0.048 Uiso d . 1 . . H
C17 -0.8431(3) 0.1007(2) -0.03491(13) 0.0406(4) Uani d . 1 . . C
H17 -0.734(3) 0.167(3) -0.0586(14) 0.049 Uiso d . 1 . . H
S1 0.05611(7) 0.76015(5) 0.33208(3) 0.03615(14) Uani d . 1 . . S
O1 0.1179(2) 0.62824(18) 0.32771(10) 0.0537(4) Uani d . 1 . . O
O2 0.1908(2) 0.90104(17) 0.30123(9) 0.0480(4) Uani d . 1 . . O
O3 0.0193(2) 0.79638(17) 0.41765(8) 0.0471(4) Uani d . 1 . . O
C18 -0.1853(3) 0.6962(2) 0.25935(11) 0.0313(4) Uani d . 1 . . C
C19 -0.3148(3) 0.7711(2) 0.26878(13) 0.0403(4) Uani d . 1 . . C
H19 -0.276(3) 0.853(3) 0.3145(15) 0.048 Uiso d . 1 . . H
C20 -0.5013(3) 0.7243(2) 0.21222(14) 0.0433(5) Uani d . 1 . . C
H20 -0.585(4) 0.779(3) 0.2201(15) 0.052 Uiso d . 1 . . H
C21 -0.5622(3) 0.6026(2) 0.14474(13) 0.0392(4) Uani d . 1 . . C
C22 -0.4328(3) 0.5269(2) 0.13670(13) 0.0429(5) Uani d . 1 . . C
H22 -0.475(3) 0.443(3) 0.0929(15) 0.051 Uiso d . 1 . . H
C23 -0.2452(3) 0.5725(2) 0.19359(13) 0.0380(4) Uani d . 1 . . C
H23 -0.161(3) 0.519(3) 0.1883(14) 0.046 Uiso d . 1 . . H
C24 -0.7647(3) 0.5547(3) 0.08199(16) 0.0592(6) Uani d . 1 . . C
H24A -0.7922 0.4580 0.0453 0.089 Uiso calc R 1 . . H
H24B -0.7590 0.6387 0.0457 0.089 Uiso calc R 1 . . H
H24C -0.8725 0.5367 0.1147 0.089 Uiso calc R 1 . . H
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'
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_site_symmetry_1
_geom_angle
C6 N1 C2 . 121.12(15)
C6 N1 C7 . 119.45(14)
C2 N1 C7 . 119.43(14)
N1 C2 C3 . 119.74(17)
C2 C3 C4 . 119.79(18)
C3 C4 C5 . 119.60(17)
C6 C5 C4 . 119.53(17)
N1 C6 C5 . 120.19(17)
C12 C7 C8 . 121.92(16)
C12 C7 N1 . 118.73(15)
C8 C7 N1 . 119.35(16)
C7 C8 C9 . 118.53(18)
C8 C9 C10 . 120.97(18)
C11 C10 C9 . 118.54(17)
C11 C10 C13 . 117.30(17)
C9 C10 C13 . 124.16(17)
C12 C11 C10 . 121.49(18)
C7 C12 C11 . 118.54(17)
C14 C13 C10 . 127.60(19)
C13 C14 C15 . 123.38(19)
C17 C15 C16 . 117.58(17)
C17 C15 C14 . 118.86(17)
C16 C15 C14 . 123.54(17)
C17 C16 C15 2_355 120.97(17)
C16 C17 C15 2_355 121.45(18)
O1 S1 O2 . 113.64(10)
O1 S1 O3 . 113.19(9)
O2 S1 O3 . 111.54(9)
O1 S1 C18 . 105.79(9)
O2 S1 C18 . 106.36(8)
O3 S1 C18 . 105.56(8)
C19 C18 C23 . 119.39(17)
C19 C18 S1 . 119.67(14)
C23 C18 S1 . 120.94(14)
C18 C19 C20 . 120.38(18)
C19 C20 C21 . 121.06(19)
C22 C21 C20 . 118.09(18)
C22 C21 C24 . 121.3(2)
C20 C21 C24 . 120.65(19)
C23 C22 C21 . 121.27(19)
C18 C23 C22 . 119.79(18)
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 C6 . 1.356(2) ?
N1 C2 . 1.359(2) ?
N1 C7 . 1.452(2) ?
C2 C3 . 1.372(3) ?
C3 C4 . 1.383(3) ?
C4 C5 . 1.383(3) ?
C5 C6 . 1.370(3) ?
C7 C12 . 1.383(3) ?
C7 C8 . 1.383(3) ?
C8 C9 . 1.389(3) ?
C9 C10 . 1.399(3) ?
C10 C11 . 1.387(3) ?
C10 C13 . 1.476(2) ?
C11 C12 . 1.384(2) ?
C13 C14 . 1.321(3) ?
C14 C15 . 1.476(2) ?
C15 C17 . 1.392(3) ?
C15 C16 . 1.393(3) ?
C16 C17 2_355 1.381(3) ?
C17 C16 2_355 1.381(3) ?
S1 O1 . 1.4481(16) ?
S1 O2 . 1.4492(13) ?
S1 O3 . 1.4585(14) ?
S1 C18 . 1.7838(18) ?
C18 C19 . 1.382(3) ?
C18 C23 . 1.383(3) ?
C19 C20 . 1.383(3) ?
C20 C21 . 1.387(3) ?
C21 C22 . 1.384(3) ?
C21 C24 . 1.514(3) ?
C22 C23 . 1.392(3) ?
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_4
_geom_torsion
C6 N1 C2 C3 . 1.5(3)
C7 N1 C2 C3 . -177.72(17)
N1 C2 C3 C4 . -2.0(3)
C2 C3 C4 C5 . 0.9(3)
C3 C4 C5 C6 . 0.8(3)
C2 N1 C6 C5 . 0.2(3)
C7 N1 C6 C5 . 179.43(17)
C4 C5 C6 N1 . -1.4(3)
C6 N1 C7 C12 . -132.14(18)
C2 N1 C7 C12 . 47.1(2)
C6 N1 C7 C8 . 48.4(2)
C2 N1 C7 C8 . -132.45(18)
C12 C7 C8 C9 . 0.0(3)
N1 C7 C8 C9 . 179.48(16)
C7 C8 C9 C10 . -0.9(3)
C8 C9 C10 C11 . 1.1(3)
C8 C9 C10 C13 . -177.68(17)
C9 C10 C11 C12 . -0.4(3)
C13 C10 C11 C12 . 178.44(17)
C8 C7 C12 C11 . 0.7(3)
N1 C7 C12 C11 . -178.83(16)
C10 C11 C12 C7 . -0.5(3)
C11 C10 C13 C14 . 173.5(2)
C9 C10 C13 C14 . -7.8(3)
C10 C13 C14 C15 . -179.92(17)
C13 C14 C15 C17 . 158.7(2)
C13 C14 C15 C16 . -19.9(3)
C17 C15 C16 C17 2_355 -0.5(3)
C14 C15 C16 C17 2_355 178.19(19)
C16 C15 C17 C16 2_355 0.5(3)
C14 C15 C17 C16 2_355 -178.25(19)
O1 S1 C18 C19 . 159.14(15)
O2 S1 C18 C19 . -79.70(16)
O3 S1 C18 C19 . 38.91(17)
O1 S1 C18 C23 . -20.74(17)
O2 S1 C18 C23 . 100.42(16)
O3 S1 C18 C23 . -140.97(15)
C23 C18 C19 C20 . -0.9(3)
S1 C18 C19 C20 . 179.17(15)
C18 C19 C20 C21 . -0.4(3)
C19 C20 C21 C22 . 1.4(3)
C19 C20 C21 C24 . -178.64(18)
C20 C21 C22 C23 . -1.0(3)
C24 C21 C22 C23 . 178.99(18)
C19 C18 C23 C22 . 1.3(3)
S1 C18 C23 C22 . -178.83(14)
C21 C22 C23 C18 . -0.3(3)
