#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224574.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_2224574
loop_
_publ_author_name
'An, Yan'
'Li, Xiao-Feng'
'Chen, Hui-Guo'
'Dong, Li-Hua'
_publ_section_title
;
 Tris[2-(2-pyridylsulfanyl)ethyl]ammonium perchlorate
;
_journal_coeditor_code           BX2246
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o101
_journal_paper_doi               10.1107/S1600536809052283
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H25 N4 S3 +, Cl O4 -'
_chemical_formula_moiety         'C21 H25 N4 S3 +, Cl O4 -'
_chemical_formula_sum            'C21 H25 Cl N4 O4 S3'
_chemical_formula_weight         529.08
_chemical_name_systematic
;
Tris[2-(2-pyridylsulfanyl)ethyl]ammonium perchlorate
;
_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                110.884(4)
_cell_angle_beta                 99.609(4)
_cell_angle_gamma                91.774(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5480(7)
_cell_length_b                   11.9753(10)
_cell_length_c                   12.9346(11)
_cell_measurement_reflns_used    3657
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.53
_cell_measurement_theta_min      2.43
_cell_volume                     1213.81(18)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0095
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6994
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.425
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0399
_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)+(0.0436P)²+0.6528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3936
_reflns_number_total             4726
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2246.cif
_cod_data_source_block           I
_cod_database_code               2224574
_cod_database_fobs_code          2224574
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
C C1 0.6881(3) 0.46034(19) 0.84074(18) 0.0474(5) Uani d . 1 . .
H H1A 0.5787 0.4756 0.8204 0.057 Uiso calc R 1 . .
H H1B 0.7181 0.4941 0.9223 0.057 Uiso calc R 1 . .
C C2 0.6983(3) 0.32631(19) 0.80047(18) 0.0496(5) Uani d . 1 . .
H H2A 0.6785 0.2988 0.8595 0.060 Uiso calc R 1 . .
H H2B 0.8064 0.3111 0.7898 0.060 Uiso calc R 1 . .
C C3 0.6641(3) 0.24033(19) 0.56478(18) 0.0474(5) Uani d . 1 . .
C C4 0.6269(3) 0.1444(2) 0.4618(2) 0.0632(6) Uani d . 1 . .
H H4 0.5527 0.0810 0.4512 0.076 Uiso calc R 1 . .
C C5 0.7022(4) 0.1453(2) 0.3761(2) 0.0703(8) Uani d . 1 . .
H H5 0.6791 0.0825 0.3064 0.084 Uiso calc R 1 . .
C C6 0.8115(3) 0.2394(2) 0.3942(2) 0.0656(7) Uani d . 1 . .
H H6 0.8643 0.2415 0.3375 0.079 Uiso calc R 1 . .
C C7 0.8414(3) 0.3303(2) 0.49763(19) 0.0569(6) Uani d . 1 . .
H H7 0.9161 0.3939 0.5097 0.068 Uiso calc R 1 . .
C C8 0.9644(2) 0.53834(19) 0.85158(17) 0.0443(5) Uani d . 1 . .
H H8A 0.9845 0.4716 0.8762 0.053 Uiso calc R 1 . .
H H8B 0.9814 0.6115 0.9181 0.053 Uiso calc R 1 . .
C C9 1.0806(3) 0.5451(2) 0.77764(19) 0.0532(5) Uani d . 1 . .
H H9A 1.0468 0.5992 0.7394 0.064 Uiso calc R 1 . .
H H9B 1.0820 0.4662 0.7208 0.064 Uiso calc R 1 . .
C C10 1.2649(3) 0.7542(2) 0.91802(19) 0.0487(5) Uani d . 1 . .
C C11 1.3855(3) 0.8231(3) 1.0063(2) 0.0660(7) Uani d . 1 . .
H H11 1.4706 0.7883 1.0335 0.079 Uiso calc R 1 . .
C C12 1.3746(4) 0.9446(3) 1.0520(2) 0.0781(9) Uani d . 1 . .
H H12 1.4517 0.9935 1.1124 0.094 Uiso calc R 1 . .
C C13 1.2506(4) 0.9930(3) 1.0086(2) 0.0755(8) Uani d . 1 . .
H H13 1.2421 1.0752 1.0380 0.091 Uiso calc R 1 . .
C C14 1.1389(3) 0.9186(2) 0.9210(2) 0.0643(6) Uani d . 1 . .
H H14 1.0550 0.9525 0.8914 0.077 Uiso calc R 1 . .
C C15 0.7377(3) 0.64094(18) 0.79479(18) 0.0481(5) Uani d . 1 . .
H H15A 0.8273 0.6933 0.7957 0.058 Uiso calc R 1 . .
H H15B 0.6980 0.6784 0.8639 0.058 Uiso calc R 1 . .
C C16 0.6077(3) 0.6288(2) 0.6955(2) 0.0555(6) Uani d . 1 . .
H H16A 0.5502 0.6998 0.7150 0.067 Uiso calc R 1 . .
H H16B 0.5330 0.5602 0.6819 0.067 Uiso calc R 1 . .
C C17 0.7470(2) 0.75988(19) 0.58998(17) 0.0447(5) Uani d . 1 . .
C C18 0.7867(3) 0.7806(2) 0.49839(19) 0.0523(5) Uani d . 1 . .
H H18 0.7791 0.7180 0.4293 0.063 Uiso calc R 1 . .
C C19 0.8374(3) 0.8954(2) 0.5120(2) 0.0577(6) Uani d . 1 . .
H H19 0.8631 0.9124 0.4518 0.069 Uiso calc R 1 . .
C C20 0.8496(3) 0.9850(2) 0.6158(2) 0.0580(6) Uani d . 1 . .
H H20 0.8848 1.0636 0.6276 0.070 Uiso calc R 1 . .
C C21 0.8088(3) 0.9557(2) 0.7016(2) 0.0565(6) Uani d . 1 . .
H H21 0.8176 1.0168 0.7717 0.068 Uiso calc R 1 . .
Cl Cl1 0.81316(7) 0.76318(5) 0.16119(4) 0.05665(17) Uani d . 1 . .
N N1 0.7943(2) 0.52226(15) 0.79143(14) 0.0386(4) Uani d . 1 . .
N N2 0.7689(2) 0.33273(15) 0.58241(14) 0.0462(4) Uani d . 1 . .
N N3 1.1428(2) 0.79961(17) 0.87518(15) 0.0518(4) Uani d . 1 . .
N N4 0.7570(2) 0.84479(16) 0.69109(15) 0.0509(4) Uani d . 1 . .
O O1 0.9039(3) 0.73699(19) 0.25035(17) 0.0908(7) Uani d . 1 . .
O O2 0.6898(4) 0.6723(2) 0.0992(3) 0.1414(12) Uani d . 1 . .
O O3 0.9173(4) 0.7694(3) 0.0890(2) 0.1406(12) Uani d . 1 . .
O O4 0.7508(3) 0.87338(17) 0.20429(19) 0.0944(7) Uani d . 1 . .
S S1 0.56374(8) 0.23770(6) 0.67216(6) 0.06351(19) Uani d . 1 . .
S S2 1.27812(8) 0.59780(6) 0.86105(7) 0.0685(2) Uani d . 1 . .
S S3 0.67777(9) 0.61051(5) 0.56746(5) 0.06103(18) Uani d . 1 . .
H H1N 0.791(3) 0.475(2) 0.724(2) 0.050(6) 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'
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 . . 112.63(16) ?
N1 C1 H1A . . 109.1 ?
C2 C1 H1A . . 109.1 ?
N1 C1 H1B . . 109.1 ?
C2 C1 H1B . . 109.1 ?
H1A C1 H1B . . 107.8 ?
C1 C2 S1 . . 116.00(16) ?
C1 C2 H2A . . 108.3 ?
S1 C2 H2A . . 108.3 ?
C1 C2 H2B . . 108.3 ?
S1 C2 H2B . . 108.3 ?
H2A C2 H2B . . 107.4 ?
N2 C3 C4 . . 122.2(2) ?
N2 C3 S1 . . 120.20(16) ?
C4 C3 S1 . . 117.62(19) ?
C5 C4 C3 . . 118.6(2) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C6 C5 C4 . . 119.4(2) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C7 C6 C5 . . 118.4(2) ?
C7 C6 H6 . . 120.8 ?
C5 C6 H6 . . 120.8 ?
N2 C7 C6 . . 123.6(2) ?
N2 C7 H7 . . 118.2 ?
C6 C7 H7 . . 118.2 ?
N1 C8 C9 . . 112.11(17) ?
N1 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
N1 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C8 C9 S2 . . 110.37(16) ?
C8 C9 H9A . . 109.6 ?
S2 C9 H9A . . 109.6 ?
C8 C9 H9B . . 109.6 ?
S2 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
N3 C10 C11 . . 123.5(2) ?
N3 C10 S2 . . 119.08(17) ?
C11 C10 S2 . . 117.41(19) ?
C12 C11 C10 . . 117.6(3) ?
C12 C11 H11 . . 121.2 ?
C10 C11 H11 . . 121.2 ?
C13 C12 C11 . . 119.7(3) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 118.6(3) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
N3 C14 C13 . . 123.9(3) ?
N3 C14 H14 . . 118.0 ?
C13 C14 H14 . . 118.0 ?
N1 C15 C16 . . 112.76(17) ?
N1 C15 H15A . . 109.0 ?
C16 C15 H15A . . 109.0 ?
N1 C15 H15B . . 109.0 ?
C16 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
C15 C16 S3 . . 114.41(17) ?
C15 C16 H16A . . 108.7 ?
S3 C16 H16A . . 108.7 ?
C15 C16 H16B . . 108.7 ?
S3 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
N4 C17 C18 . . 123.8(2) ?
N4 C17 S3 . . 119.39(16) ?
C18 C17 S3 . . 116.78(16) ?
C19 C18 C17 . . 118.4(2) ?
C19 C18 H18 . . 120.8 ?
C17 C18 H18 . . 120.8 ?
C18 C19 C20 . . 119.1(2) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
C21 C20 C19 . . 118.3(2) ?
C21 C20 H20 . . 120.8 ?
C19 C20 H20 . . 120.8 ?
N4 C21 C20 . . 124.3(2) ?
N4 C21 H21 . . 117.8 ?
C20 C21 H21 . . 117.8 ?
O4 Cl1 O2 . . 110.19(16) ?
O4 Cl1 O3 . . 109.95(18) ?
O2 Cl1 O3 . . 108.4(2) ?
O4 Cl1 O1 . . 109.82(13) ?
O2 Cl1 O1 . . 111.28(18) ?
O3 Cl1 O1 . . 107.10(17) ?
C8 N1 C15 . . 110.80(16) ?
C8 N1 C1 . . 110.78(15) ?
C15 N1 C1 . . 111.01(16) ?
C8 N1 H1N . . 107.1(16) ?
C15 N1 H1N . . 110.9(16) ?
C1 N1 H1N . . 106.1(15) ?
C3 N2 C7 . . 117.69(19) ?
C10 N3 C14 . . 116.7(2) ?
C17 N4 C21 . . 116.07(19) ?
C3 S1 C2 . . 104.27(10) ?
C10 S2 C9 . . 101.18(11) ?
C17 S3 C16 . . 102.03(11) ?
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
C1 N1 . 1.506(3) ?
C1 C2 . 1.511(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 S1 . 1.798(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N2 . 1.330(3) ?
C3 C4 . 1.393(3) ?
C3 S1 . 1.758(2) ?
C4 C5 . 1.375(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.368(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.368(3) ?
C6 H6 . 0.9300 ?
C7 N2 . 1.339(3) ?
C7 H7 . 0.9300 ?
C8 N1 . 1.502(3) ?
C8 C9 . 1.508(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 S2 . 1.804(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N3 . 1.323(3) ?
C10 C11 . 1.389(3) ?
C10 S2 . 1.766(2) ?
C11 C12 . 1.375(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.358(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.362(4) ?
C13 H13 . 0.9300 ?
C14 N3 . 1.337(3) ?
C14 H14 . 0.9300 ?
C15 N1 . 1.504(2) ?
C15 C16 . 1.512(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 S3 . 1.797(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 N4 . 1.327(3) ?
C17 C18 . 1.385(3) ?
C17 S3 . 1.772(2) ?
C18 C19 . 1.369(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.372(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.369(3) ?
C20 H20 . 0.9300 ?
C21 N4 . 1.339(3) ?
C21 H21 . 0.9300 ?
Cl1 O4 . 1.3980(18) ?
Cl1 O2 . 1.402(2) ?
Cl1 O3 . 1.411(3) ?
Cl1 O1 . 1.416(2) ?
N1 H1N . 0.85(2) ?
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
N1 H(1N) N2 . 0.85(2) 1.98(2) 2.812(2) 165(3) yes
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
N1 C1 C2 S1 . . . . -88.3(2) ?
N2 C3 C4 C5 . . . . 0.4(3) ?
S1 C3 C4 C5 . . . . 179.12(19) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
C4 C5 C6 C7 . . . . -0.4(4) ?
C5 C6 C7 N2 . . . . -0.3(4) ?
N1 C8 C9 S2 . . . . 167.02(14) ?
N3 C10 C11 C12 . . . . 1.1(3) ?
S2 C10 C11 C12 . . . . -179.07(18) ?
C10 C11 C12 C13 . . . . -1.5(4) ?
C11 C12 C13 C14 . . . . 0.7(4) ?
C12 C13 C14 N3 . . . . 0.6(4) ?
N1 C15 C16 S3 . . . . -79.1(2) ?
N4 C17 C18 C19 . . . . -0.8(3) ?
S3 C17 C18 C19 . . . . 178.63(18) ?
C17 C18 C19 C20 . . . . 1.1(3) ?
C18 C19 C20 C21 . . . . -0.6(4) ?
C19 C20 C21 N4 . . . . -0.2(4) ?
C9 C8 N1 C15 . . . . -82.6(2) ?
C9 C8 N1 C1 . . . . 153.72(17) ?
C16 C15 N1 C8 . . . . 152.34(18) ?
C16 C15 N1 C1 . . . . -84.1(2) ?
C2 C1 N1 C8 . . . . -78.5(2) ?
C2 C1 N1 C15 . . . . 157.92(18) ?
C4 C3 N2 C7 . . . . -1.1(3) ?
S1 C3 N2 C7 . . . . -179.76(17) ?
C6 C7 N2 C3 . . . . 1.1(3) ?
C11 C10 N3 C14 . . . . 0.2(3) ?
S2 C10 N3 C14 . . . . -179.71(17) ?
C13 C14 N3 C10 . . . . -1.0(4) ?
C18 C17 N4 C21 . . . . 0.1(3) ?
S3 C17 N4 C21 . . . . -179.39(17) ?
C20 C21 N4 C17 . . . . 0.4(4) ?
N2 C3 S1 C2 . . . . -27.5(2) ?
C4 C3 S1 C2 . . . . 153.81(18) ?
C1 C2 S1 C3 . . . . 85.25(17) ?
N3 C10 S2 C9 . . . . -13.36(19) ?
C11 C10 S2 C9 . . . . 166.76(17) ?
C8 C9 S2 C10 . . . . -79.99(17) ?
N4 C17 S3 C16 . . . . 9.5(2) ?
C18 C17 S3 C16 . . . . -170.05(17) ?
C15 C16 S3 C17 . . . . -79.31(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655965
