#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006476.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_2006476
loop_
_publ_author_name
'Jones, P. G.'
'Kus, P.'
_publ_section_title
;
 2,13-Dithia[3]metacyclo[3](2,3)naphthalenophane and
 2,13-Dithia[3]metacyclo[3](1,7)naphthalenophane
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1307
_journal_page_last               1310
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C20 H18 S2'
_chemical_formula_weight         322.46
_chemical_name_systematic
;
 2,13-Dithia[3]metacyclo[3](2,3)-naphthalenophane
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 105.524(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.604(2)
_cell_length_b                   9.7659(12)
_cell_length_c                   17.8787(18)
_cell_measurement_reflns_used    62
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      3.5
_cell_volume                     3298.0(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       \w_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4740
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.025
_refine_ls_goodness_of_fit_obs   1.119
_refine_ls_hydrogen_treatment    'H atoms riding: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_restrained_S_obs      1.119
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_obs          0.0354
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.4203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0976
_refine_ls_wR_factor_obs         0.0934
_reflns_number_observed          2942
_reflns_number_total             3775
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1295.cif
_[local]_cod_data_source_block   1
_cod_original_cell_volume        3298.1(6)
_cod_database_code               2006476
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0413(9) 0.0463(10) 0.0548(10) 0.0113(8) 0.0225(8) 0.0063(8)
S2 0.0323(2) 0.0496(2) 0.0370(2) -0.00535(17) 0.01770(16) 0.00705(17)
C3 0.0272(7) 0.0308(7) 0.0339(7) -0.0023(6) 0.0083(6) 0.0056(6)
C4 0.0204(6) 0.0272(6) 0.0259(6) 0.0008(5) 0.0045(5) 0.0060(5)
C5 0.0272(7) 0.0309(7) 0.0251(6) 0.0004(6) 0.0085(5) 0.0051(5)
C5' 0.0240(6) 0.0263(7) 0.0274(6) 0.0027(5) 0.0028(5) 0.0058(5)
C6 0.0380(8) 0.0315(8) 0.0323(7) 0.0008(6) 0.0059(6) 0.0007(6)
C7 0.0381(8) 0.0278(7) 0.0456(9) -0.0013(6) -0.0027(7) -0.0006(7)
C8 0.0262(7) 0.0285(7) 0.0592(10) -0.0033(6) 0.0022(7) 0.0078(7)
C9 0.0231(7) 0.0327(8) 0.0511(9) 0.0022(6) 0.0114(6) 0.0089(7)
C9' 0.0199(6) 0.0268(7) 0.0345(7) 0.0037(5) 0.0057(5) 0.0072(6)
C10 0.0238(7) 0.0341(7) 0.0321(7) 0.0050(6) 0.0121(6) 0.0046(6)
C11 0.0254(6) 0.0272(7) 0.0258(6) 0.0039(5) 0.0060(5) 0.0016(5)
C12 0.0386(8) 0.0334(8) 0.0315(7) 0.0016(7) 0.0112(6) -0.0031(6)
S13 0.0458(2) 0.0518(3) 0.0306(2) -0.00183(19) 0.01860(17) -0.00781(17)
C14 0.0484(9) 0.0401(9) 0.0298(7) -0.0043(7) 0.0102(7) 0.0048(6)
C15 0.0362(8) 0.0280(7) 0.0314(7) 0.0006(6) 0.0011(6) 0.0066(6)
C16 0.0470(10) 0.0351(8) 0.0346(8) -0.0011(7) -0.0052(7) 0.0057(6)
C17 0.0376(9) 0.0373(9) 0.0541(10) -0.0062(7) -0.0130(8) 0.0094(8)
C18 0.0261(8) 0.0413(9) 0.0660(12) 0.0013(7) 0.0055(8) 0.0198(8)
C19 0.0297(7) 0.0327(8) 0.0440(8) 0.0094(6) 0.0071(7) 0.0116(6)
C20 0.0285(7) 0.0273(7) 0.0342(7) 0.0029(6) 0.0015(6) 0.0057(6)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.80548(9) 0.42555(18) 0.61392(10) 0.0456(4) Uani d . 1 C
H1A 0.7753 0.3439 0.5973 0.055 Uiso calc R 1 H
H1B 0.8535 0.4039 0.6091 0.055 Uiso calc R 1 H
S2 0.76915(2) 0.56911(4) 0.54973(2) 0.03799(12) Uani d . 1 S
C3 0.69794(7) 0.62890(15) 0.58811(8) 0.0306(3) Uani d . 1 C
H3A 0.7187 0.6572 0.6426 0.037 Uiso calc R 1 H
H3B 0.6774 0.7118 0.5587 0.037 Uiso calc R 1 H
C4 0.63775(7) 0.52988(14) 0.58664(8) 0.0248(3) Uani d . 1 C
C5 0.61580(7) 0.43933(14) 0.52603(8) 0.0274(3) Uani d . 1 C
H5 0.6396 0.4389 0.4862 0.033 Uiso calc R 1 H
C5' 0.55919(7) 0.34692(14) 0.52069(8) 0.0267(3) Uani d . 1 C
C6 0.53663(8) 0.25318(15) 0.45833(9) 0.0346(3) Uani d . 1 C
H6 0.5595 0.2527 0.4177 0.042 Uiso calc R 1 H
C7 0.48259(8) 0.16363(16) 0.45583(10) 0.0398(4) Uani d . 1 C
H7 0.4685 0.1009 0.4139 0.048 Uiso calc R 1 H
C8 0.44784(8) 0.16396(16) 0.51503(10) 0.0397(4) Uani d . 1 C
H8 0.4105 0.1009 0.5130 0.048 Uiso calc R 1 H
C9 0.46721(7) 0.25413(15) 0.57559(10) 0.0354(3) Uani d . 1 C
H9 0.4427 0.2541 0.6148 0.042 Uiso calc R 1 H
C9' 0.52373(7) 0.34791(14) 0.58045(8) 0.0274(3) Uani d . 1 C
C10 0.54697(7) 0.44073(14) 0.64243(8) 0.0291(3) Uani d . 1 C
H10 0.5236 0.4414 0.6827 0.035 Uiso calc R 1 H
C11 0.60200(7) 0.53019(14) 0.64695(8) 0.0263(3) Uani d . 1 C
C12 0.62261(8) 0.62952(16) 0.71460(8) 0.0342(3) Uani d . 1 C
H12A 0.5904 0.7093 0.7025 0.041 Uiso calc R 1 H
H12B 0.6710 0.6632 0.7182 0.041 Uiso calc R 1 H
S13 0.62111(2) 0.56448(5) 0.80926(2) 0.04112(13) Uani d . 1 S
C14 0.68317(9) 0.42090(17) 0.82338(9) 0.0395(4) Uani d . 1 C
H14A 0.6962 0.3938 0.8788 0.047 Uiso calc R 1 H
H14B 0.6595 0.3417 0.7925 0.047 Uiso calc R 1 H
C15 0.74921(8) 0.45471(15) 0.80000(9) 0.0334(3) Uani d . 1 C
C16 0.80325(9) 0.53547(17) 0.84567(10) 0.0420(4) Uani d . 1 C
H16 0.8009 0.5645 0.8956 0.050 Uiso calc R 1 H
C17 0.85999(9) 0.57329(17) 0.81857(11) 0.0479(5) Uani d . 1 C
H17 0.8974 0.6253 0.8509 0.057 Uiso calc R 1 H
C18 0.86309(8) 0.53621(17) 0.74444(11) 0.0458(4) Uani d . 1 C
H18 0.9017 0.5657 0.7258 0.055 Uiso calc R 1 H
C19 0.80973(8) 0.45590(15) 0.69735(10) 0.0360(3) Uani d . 1 C
C20 0.75479(8) 0.41220(15) 0.72743(8) 0.0313(3) Uani d . 1 C
H20 0.7201 0.3516 0.6976 0.038 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'
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
C19 C1 S2 112.37(12) y
C3 S2 C1 102.68(7) y
C4 C3 S2 117.53(10) y
C5 C4 C11 118.73(12) ?
C5 C4 C3 120.02(12) ?
C11 C4 C3 121.24(12) y
C4 C5 C5' 122.55(13) ?
C5 C5' C6 122.62(13) ?
C5 C5' C9' 118.53(12) ?
C6 C5' C9' 118.85(13) ?
C7 C6 C5' 121.00(15) ?
C6 C7 C8 120.18(15) ?
C9 C8 C7 120.68(14) ?
C8 C9 C9' 120.63(15) ?
C10 C9' C5' 118.35(12) ?
C10 C9' C9 123.00(13) ?
C5' C9' C9 118.64(13) ?
C11 C10 C9' 122.60(12) ?
C10 C11 C4 119.23(13) ?
C10 C11 C12 119.38(12) ?
C4 C11 C12 121.37(13) y
C11 C12 S13 116.86(11) y
C12 S13 C14 102.75(7) y
C15 C14 S13 112.62(11) y
C20 C15 C16 118.45(15) ?
C20 C15 C14 118.84(14) y
C16 C15 C14 122.54(15) ?
C17 C16 C15 120.25(17) ?
C16 C17 C18 120.71(16) ?
C17 C18 C19 120.30(16) ?
C20 C19 C18 118.12(16) ?
C20 C19 C1 118.70(15) y
C18 C19 C1 122.94(16) ?
C19 C20 C15 121.96(14) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C19 1.501(2) y
C1 S2 1.8310(18) y
S2 C3 1.8093(15) y
C3 C4 1.5204(19) y
C4 C5 1.3754(19) ?
C4 C11 1.4347(19) y
C5 C5' 1.4137(19) ?
C5' C6 1.419(2) ?
C5' C9' 1.4221(19) ?
C6 C7 1.365(2) ?
C7 C8 1.404(2) ?
C8 C9 1.368(2) ?
C9 C9' 1.4221(19) ?
C9' C10 1.410(2) ?
C10 C11 1.3737(19) ?
C11 C12 1.518(2) y
C12 S13 1.8152(15) y
S13 C14 1.8292(17) y
C14 C15 1.500(2) y
C15 C20 1.394(2) y
C15 C16 1.396(2) ?
C16 C17 1.377(3) ?
C17 C18 1.391(3) ?
C18 C19 1.395(2) ?
C19 C20 1.393(2) y
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
C19 C1 S2 C3 -40.99(14) y
C1 S2 C3 C4 -61.88(12) y
S2 C3 C4 C5 -35.24(17) ?
S2 C3 C4 C11 145.89(11) y
C11 C4 C5 C5' 0.3(2) ?
C3 C4 C5 C5' -178.63(12) ?
C4 C5 C5' C6 -179.80(13) ?
C4 C5 C5' C9' -0.05(19) ?
C5 C5' C6 C7 178.76(13) ?
C9' C5' C6 C7 -1.0(2) ?
C5' C6 C7 C8 0.6(2) ?
C6 C7 C8 C9 0.4(2) ?
C7 C8 C9 C9' -1.0(2) ?
C5 C5' C9' C10 -0.27(18) ?
C6 C5' C9' C10 179.50(13) ?
C5 C5' C9' C9 -179.39(12) ?
C6 C5' C9' C9 0.38(19) ?
C8 C9 C9' C10 -178.46(13) ?
C8 C9 C9' C5' 0.6(2) ?
C5' C9' C10 C11 0.4(2) ?
C9 C9' C10 C11 179.45(13) ?
C9' C10 C11 C4 -0.1(2) ?
C9' C10 C11 C12 178.44(13) ?
C5 C4 C11 C10 -0.17(19) ?
C3 C4 C11 C10 178.71(12) ?
C5 C4 C11 C12 -178.73(13) ?
C3 C4 C11 C12 0.1(2) y
C10 C11 C12 S13 39.74(17) ?
C4 C11 C12 S13 -141.70(12) y
C11 C12 S13 C14 58.54(13) y
C12 S13 C14 C15 43.56(13) y
S13 C14 C15 C20 -99.20(14) y
S13 C14 C15 C16 76.11(16) ?
C20 C15 C16 C17 0.9(2) ?
C14 C15 C16 C17 -174.40(14) ?
C15 C16 C17 C18 2.5(2) ?
C16 C17 C18 C19 -2.2(2) ?
C17 C18 C19 C20 -1.4(2) ?
C17 C18 C19 C1 172.89(15) ?
S2 C1 C19 C20 95.84(15) ?
S2 C1 C19 C18 -78.40(17) ?
C18 C19 C20 C15 4.9(2) ?
C1 C19 C20 C15 -169.65(14) y
C16 C15 C20 C19 -4.7(2) ?
C14 C15 C20 C19 170.85(14) y