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#$Date: 2016-03-26 17:11:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180380 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/49/7204994.cif $
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#
# 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_7204994
_publ_section_title
;
 Cyclic thiatetraynes: syntheses and structural properties
;
_journal_issue                   1
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              72
_journal_paper_doi               10.1039/b108403h
_journal_year                    2002
_chemical_formula_sum            'C16 H16 S2'
_chemical_formula_weight         272.4
_chemical_name_systematic
;
1,10-Dithiacyclooctadeca-3,7,12,16-tetrayne (5)
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.846(2)
_cell_length_b                   9.030(2)
_cell_length_c                   16.153(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      9
_cell_volume                     1436.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  NONIUS_CAD4
_diffrn_measurement_method       ω-2θ-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  0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1992
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        3.3
_diffrn_standards_interval_count 60
_diffrn_standards_interval_time  100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.35
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            polyhedron
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colourless
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    'refined isotropic'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0707P)²+0.1821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                1229
_reflns_number_total             1712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108403h.txt
_cod_data_source_block           339RITTM_5inpaper
_cod_database_code               7204994
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'
'-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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13119(4) 0.01974(5) 0.24841(2) 0.04096(17) Uani 1 1 d . . .
C2 C 0.00637(17) 0.09171(19) 0.32087(12) 0.0434(4) Uani 1 1 d . . .
C3 C -0.06866(15) -0.02419(17) 0.36487(9) 0.0376(4) Uani 1 1 d . . .
C4 C -0.12974(15) -0.11857(18) 0.39950(10) 0.0363(3) Uani 1 1 d . . .
C5 C -0.20942(17) -0.2356(2) 0.43975(10) 0.0424(4) Uani 1 1 d . . .
C6 C 0.33993(17) 0.1791(2) 0.51860(10) 0.0436(4) Uani 1 1 d . . .
C7 C 0.31292(15) 0.08380(19) 0.44747(10) 0.0401(4) Uani 1 1 d . . .
C8 C 0.28472(16) 0.00702(18) 0.38948(10) 0.0395(4) Uani 1 1 d . . .
C9 C 0.23894(19) -0.08241(19) 0.31980(10) 0.0427(4) Uani 1 1 d . . .
H2A H 0.049(2) 0.158(2) 0.3614(12) 0.062(6) Uiso 1 1 d . . .
H2B H -0.050(2) 0.158(2) 0.2855(14) 0.066(6) Uiso 1 1 d . . .
H5A H -0.155(2) -0.282(2) 0.4826(12) 0.048(5) Uiso 1 1 d . . .
H5B H -0.232(2) -0.310(2) 0.3993(13) 0.066(6) Uiso 1 1 d . . .
H6A H 0.386(2) 0.266(3) 0.4994(12) 0.064(7) Uiso 1 1 d . . .
H6B H 0.390(2) 0.124(3) 0.5587(13) 0.061(6) Uiso 1 1 d . . .
H9B H 0.194(2) -0.169(2) 0.3394(11) 0.055(5) Uiso 1 1 d . . .
H9A H 0.317(2) -0.120(2) 0.2857(14) 0.064(6) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0414(3) 0.0492(3) 0.0323(3) 0.00454(16) 0.00613(15) -0.00160(17)
C2 0.0370(8) 0.0408(9) 0.0523(9) 0.0065(7) 0.0094(7) 0.0022(7)
C3 0.0279(7) 0.0464(8) 0.0385(8) 0.0018(7) 0.0023(6) 0.0008(7)
C4 0.0301(7) 0.0442(8) 0.0348(7) -0.0023(7) 0.0008(6) -0.0007(6)
C5 0.0412(8) 0.0445(9) 0.0415(9) -0.0003(7) 0.0047(7) -0.0073(7)
C6 0.0325(7) 0.0584(11) 0.0397(8) 0.0029(8) 0.0008(7) -0.0114(8)
C7 0.0332(8) 0.0494(9) 0.0377(8) 0.0086(7) 0.0048(6) 0.0012(7)
C8 0.0381(8) 0.0438(9) 0.0366(7) 0.0080(6) 0.0057(6) 0.0060(7)
C9 0.0504(9) 0.0382(8) 0.0394(8) 0.0023(7) 0.0096(7) 0.0064(8)
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C9 99.64(8) . . ?
C3 C2 S1 113.45(12) . . ?
C3 C2 H2A 109.0(12) . . ?
S1 C2 H2A 111.1(13) . . ?
C3 C2 H2B 115.3(13) . . ?
S1 C2 H2B 102.9(13) . . ?
H2A C2 H2B 104.6(17) . . ?
C4 C3 C2 179.18(17) . . ?
C3 C4 C5 177.73(17) . . ?
C4 C5 C6 113.67(15) . 5_556 ?
C4 C5 H5A 109.2(12) . . ?
C6 C5 H5A 107.2(11) 5_556 . ?
C4 C5 H5B 109.2(12) . . ?
C6 C5 H5B 109.3(13) 5_556 . ?
H5A C5 H5B 108.1(18) . . ?
C7 C6 C5 112.81(14) . 5_556 ?
C7 C6 H6A 108.3(12) . . ?
C5 C6 H6A 105.4(12) 5_556 . ?
C7 C6 H6B 108.9(13) . . ?
C5 C6 H6B 108.1(13) 5_556 . ?
H6A C6 H6B 113.3(17) . . ?
C8 C7 C6 177.08(17) . . ?
C7 C8 C9 175.30(17) . . ?
C8 C9 S1 112.91(12) . . ?
C8 C9 H9B 110.0(12) . . ?
S1 C9 H9B 110.6(12) . . ?
C8 C9 H9A 112.1(13) . . ?
S1 C9 H9A 105.6(13) . . ?
H9B C9 H9A 105.2(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.8173(17) . ?
S1 C9 1.8184(18) . ?
C2 C3 1.465(2) . ?
C2 H2A 0.98(2) . ?
C2 H2B 1.00(2) . ?
C3 C4 1.184(2) . ?
C4 C5 1.468(2) . ?
C5 C6 1.538(2) 5_556 ?
C5 H5A 0.97(2) . ?
C5 H5B 0.97(2) . ?
C6 C7 1.460(2) . ?
C6 C5 1.538(2) 5_556 ?
C6 H6A 0.96(2) . ?
C6 H6B 0.95(2) . ?
C7 C8 1.198(2) . ?
C8 C9 1.457(2) . ?
C9 H9B 0.95(2) . ?
C9 H9A 1.00(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 S1 C2 C3 -60.71(15) . . . . ?
S1 C2 C3 C4 -55(12) . . . . ?
C2 C3 C4 C5 -34(15) . . . . ?
C3 C4 C5 C6 -76(4) . . . 5_556 ?
C5 C6 C7 C8 6(4) 5_556 . . . ?
C6 C7 C8 C9 4(5) . . . . ?
C7 C8 C9 S1 48(2) . . . . ?
C2 S1 C9 C8 -52.58(14) . . . . ?
