#------------------------------------------------------------------------------
#$Date: 2019-11-08 04:31:40 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225372 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/27/1552774.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_1552774
loop_
_publ_author_name
'TOYAMA, Mari'
'CHAYAMA, Kenji'
_publ_section_title
;
 Crystal Structure of 6-Aza-3,9-dithiaundecane Hydrochloride
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              55
_journal_paper_doi               10.2116/xraystruct.35.55
_journal_volume                  35
_journal_year                    2019
_chemical_formula_moiety         'C8 H20 Cl N S2'
_chemical_formula_sum            'C8 H20 Cl N S2'
_chemical_formula_weight         229.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   25.0091(4)
_cell_length_b                   5.39364(10)
_cell_length_c                   9.37759(19)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    173
_cell_measurement_theta_max      74.24
_cell_measurement_theta_min      7.07
_cell_volume                     1264.94(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3360
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.206
_diffrn_reflns_theta_min         7.083
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.401
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     61
_refine_ls_number_reflns         1162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0472P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1057
_reflns_number_total             1162
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            35_55_1.txt
_cod_data_source_block           ATU-HCl
_cod_database_code               1552774
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2-Y,+Z
3 1/2+X,-Y,1/2-Z
4 -X,1/2+Y,1/2-Z
5 -X,-Y,-Z
6 -1/2+X,-1/2+Y,-Z
7 -1/2-X,+Y,-1/2+Z
8 +X,-1/2-Y,-1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl 0.2500 0.7500 0.72812(6) 0.0310(2) Uani 1 2 d S T P
S1 S 0.40858(2) 0.32058(8) 0.46107(5) 0.03397(19) Uani 1 1 d . . .
N1 N 0.2500 0.2500 0.5632(2) 0.0239(4) Uani 1 2 d S T P
H5 H 0.2499(7) 0.387(3) 0.618(2) 0.039(5) Uiso 1 1 d . . .
C1 C 0.29975(7) 0.2622(3) 0.47516(16) 0.0270(4) Uani 1 1 d . . .
H1A H 0.2973 0.4039 0.4083 0.032 Uiso 1 1 calc R U .
H1B H 0.3031 0.1086 0.4181 0.032 Uiso 1 1 calc R U .
C2 C 0.34875(7) 0.2922(3) 0.56770(18) 0.0314(4) Uani 1 1 d . . .
H2A H 0.3521 0.1469 0.6316 0.038 Uiso 1 1 calc R U .
H2B H 0.3447 0.4418 0.6279 0.038 Uiso 1 1 calc R U .
C3 C 0.40170(7) 0.6357(3) 0.3972(2) 0.0354(4) Uani 1 1 d . . .
H3A H 0.3674 0.6544 0.3456 0.042 Uiso 1 1 calc R U .
H3B H 0.4017 0.7522 0.4787 0.042 Uiso 1 1 calc R U .
C4 C 0.44797(8) 0.6944(4) 0.2980(3) 0.0458(5) Uani 1 1 d . . .
H4A H 0.4480 0.5771 0.2182 0.055 Uiso 1 1 calc R U .
H4B H 0.4817 0.6803 0.3505 0.055 Uiso 1 1 calc R U .
H4C H 0.4441 0.8636 0.2614 0.055 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 S1 C3 100.61(8) . .
C1 N1 C1 112.95(17) . 2
C1 N1 H5 106.4(12) . .
C1 N1 H5 110.4(12) 2 .
N1 C1 C2 111.28(12) . .
N1 C1 H1A 109.4 . .
C2 C1 H1A 109.4 . .
N1 C1 H1B 109.4 . .
C2 C1 H1B 109.4 . .
H1A C1 H1B 108.0 . .
C1 C2 S1 111.30(11) . .
C1 C2 H2A 109.4 . .
S1 C2 H2A 109.4 . .
C1 C2 H2B 109.4 . .
S1 C2 H2B 109.4 . .
H2A C2 H2B 108.0 . .
C4 C3 S1 109.05(12) . .
C4 C3 H3A 109.9 . .
S1 C3 H3A 109.9 . .
C4 C3 H3B 109.9 . .
S1 C3 H3B 109.9 . .
H3A C3 H3B 108.3 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.8062(17) .
S1 C3 1.8102(18) .
N1 C1 1.4945(19) .
N1 C1 1.4946(19) 2
N1 H5 0.90(2) .
C1 C2 1.510(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.518(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H5 Cl1 . . 3.1088(10) 0.900 2.214 172.9 no
N1 H5 Cl1 2_555 1_545 3.1088(10) 0.900 2.214 172.9 no
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_site_symmetry_1
C1 N1 C1 C2 176.07(15) 2
N1 C1 C2 S1 -177.49(10) .
C3 S1 C2 C1 75.21(13) .
C2 S1 C3 C4 -177.64(14) .
