#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006477.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_2006477
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](1,7)-naphthalenophane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.28(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.846(2)
_cell_length_b                   13.178(3)
_cell_length_c                   13.876(3)
_cell_measurement_reflns_used    59
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      4.5
_cell_volume                     1586.3(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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3132
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.921
_refine_ls_goodness_of_fit_obs   1.064
_refine_ls_hydrogen_treatment    'H atoms riding: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_restrained_S_obs      1.064
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_obs          0.0513
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0671P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1273
_refine_ls_wR_factor_obs         0.1147
_reflns_number_observed          1766
_reflns_number_total             2792
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1295.cif
_[local]_cod_data_source_block   2
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2006477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.043(2) 0.038(2) 0.047(2) -0.0050(18) -0.0057(18) 0.0026(18)
S2 0.0359(5) 0.0399(5) 0.0565(6) 0.0086(4) 0.0056(4) 0.0097(5)
C3 0.052(2) 0.033(2) 0.050(2) -0.0010(18) 0.0153(19) 0.0074(17)
C4 0.040(2) 0.0283(18) 0.040(2) 0.0003(16) 0.0142(17) 0.0098(16)
C5 0.050(2) 0.0294(19) 0.046(2) -0.0035(17) 0.0151(19) 0.0113(17)
C6 0.078(3) 0.0301(19) 0.039(2) 0.012(2) 0.023(2) 0.0106(17)
C6' 0.053(2) 0.0194(16) 0.0260(18) 0.0019(16) 0.0091(16) 0.0047(14)
C7 0.080(3) 0.0277(19) 0.032(2) 0.001(2) 0.008(2) 0.0025(16)
C8 0.072(3) 0.0302(19) 0.033(2) -0.005(2) -0.002(2) -0.0007(17)
C9 0.047(2) 0.0305(19) 0.035(2) -0.0021(16) 0.0020(17) 0.0058(16)
C10 0.036(2) 0.0261(17) 0.0317(19) -0.0003(15) 0.0034(15) 0.0088(15)
C10' 0.050(2) 0.0209(17) 0.0290(18) 0.0044(16) -0.0015(16) 0.0048(14)
C11 0.055(2) 0.0242(18) 0.0307(19) 0.0040(17) 0.0098(18) 0.0011(15)
C12 0.036(2) 0.0305(18) 0.0351(19) 0.0002(16) -0.0010(16) 0.0031(16)
S13 0.0497(6) 0.0297(5) 0.0322(5) -0.0019(4) 0.0016(4) 0.0024(4)
C14 0.037(2) 0.046(2) 0.032(2) 0.0014(17) 0.0064(16) -0.0016(17)
C15 0.0371(19) 0.0344(18) 0.0248(17) 0.0021(16) 0.0066(15) -0.0062(15)
C16 0.037(2) 0.043(2) 0.0305(19) 0.0099(18) 0.0079(16) -0.0031(17)
C17 0.056(2) 0.0301(19) 0.0332(19) 0.0143(18) 0.0049(18) 0.0003(16)
C18 0.048(2) 0.0277(18) 0.0281(18) -0.0015(17) 0.0039(16) -0.0054(15)
C19 0.038(2) 0.0314(18) 0.0229(17) -0.0006(16) -0.0004(15) -0.0040(14)
C20 0.041(2) 0.0278(18) 0.0267(17) 0.0052(16) 0.0002(15) -0.0035(14)
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 0.0991(4) 0.4128(3) 0.1183(3) 0.0445(10) Uani d . 1 C
H1A 0.0611 0.3461 0.1359 0.053 Uiso calc R 1 H
H1B 0.0532 0.4260 0.0484 0.053 Uiso calc R 1 H
S2 0.03350(11) 0.50952(7) 0.19302(8) 0.0446(3) Uani d . 1 S
C3 0.1074(4) 0.4605(3) 0.3168(3) 0.0442(10) Uani d . 1 C
H3A 0.0189 0.4423 0.3474 0.053 Uiso calc R 1 H
H3B 0.1663 0.3975 0.3113 0.053 Uiso calc R 1 H
C4 0.2086(4) 0.5329(2) 0.3828(3) 0.0354(8) Uani d . 1 C
C5 0.1575(5) 0.5794(3) 0.4612(3) 0.0409(9) Uani d . 1 C
H5 0.0549 0.5681 0.4699 0.049 Uiso calc R 1 H
C6 0.2541(5) 0.6415(3) 0.5262(3) 0.0475(10) Uani d . 1 C
H6 0.2187 0.6708 0.5802 0.057 Uiso calc R 1 H
C6' 0.4069(4) 0.6615(2) 0.5122(2) 0.0327(8) Uani d . 1 C
C7 0.5079(5) 0.7235(3) 0.5783(3) 0.0468(10) Uani d . 1 C
H7 0.4738 0.7529 0.6328 0.056 Uiso calc R 1 H
C8 0.6533(5) 0.7414(3) 0.5650(3) 0.0468(10) Uani d . 1 C
H8 0.7216 0.7818 0.6108 0.056 Uiso calc R 1 H
C9 0.7026(4) 0.6998(3) 0.4831(2) 0.0385(9) Uani d . 1 C
H9 0.8040 0.7147 0.4742 0.046 Uiso calc R 1 H
C10 0.6114(4) 0.6391(2) 0.4156(2) 0.0317(8) Uani d . 1 C
C10' 0.4567(4) 0.6167(2) 0.4301(2) 0.0345(8) Uani d . 1 C
C11 0.3564(4) 0.5530(2) 0.3675(2) 0.0366(9) Uani d . 1 C
H11 0.3898 0.5227 0.3132 0.044 Uiso calc R 1 H
C12 0.6685(4) 0.6002(3) 0.3286(2) 0.0350(8) Uani d . 1 C
H12A 0.6368 0.5286 0.3164 0.042 Uiso calc R 1 H
H12B 0.7825 0.6032 0.3413 0.042 Uiso calc R 1 H
S13 0.58950(11) 0.67682(7) 0.22060(6) 0.0381(3) Uani d . 1 S
C14 0.6024(4) 0.5896(3) 0.1199(2) 0.0386(9) Uani d . 1 C
H14A 0.5598 0.6229 0.0565 0.046 Uiso calc R 1 H
H14B 0.7120 0.5736 0.1209 0.046 Uiso calc R 1 H
C15 0.5152(4) 0.4924(3) 0.1280(2) 0.0320(8) Uani d . 1 C
C16 0.5930(4) 0.4023(3) 0.1558(2) 0.0365(8) Uani d . 1 C
H16 0.7021 0.3997 0.1647 0.044 Uiso calc R 1 H
C17 0.5100(4) 0.3163(3) 0.1705(2) 0.0403(9) Uani d . 1 C
H17 0.5633 0.2546 0.1889 0.048 Uiso calc R 1 H
C18 0.3520(4) 0.3186(3) 0.1588(2) 0.0351(8) Uani d . 1 C
H18 0.2976 0.2593 0.1709 0.042 Uiso calc R 1 H
C19 0.2721(4) 0.4077(2) 0.1294(2) 0.0316(8) Uani d . 1 C
C20 0.3551(4) 0.4929(2) 0.1130(2) 0.0326(8) Uani d . 1 C
H20 0.3011 0.5535 0.0910 0.039 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 113.9(2) y
C1 S2 C3 101.15(17) y
C4 C3 S2 114.2(2) y
C11 C4 C5 119.4(3) ?
C11 C4 C3 119.9(3) y
C5 C4 C3 120.7(3) ?
C6 C5 C4 121.0(4) ?
C5 C6 C6' 120.1(4) ?
C7 C6' C10' 120.2(3) ?
C7 C6' C6 121.0(3) ?
C10' C6' C6 118.7(3) ?
C8 C7 C6' 120.6(4) ?
C7 C8 C9 119.7(4) ?
C10 C9 C8 123.2(4) ?
C9 C10 C10' 118.0(3) ?
C9 C10 C12 120.6(3) ?
C10' C10 C12 121.4(3) y
C11 C10' C6' 119.2(3) ?
C11 C10' C10 122.6(3) y
C6' C10' C10 118.3(3) ?
C4 C11 C10' 121.6(3) ?
C10 C12 S13 109.9(2) y
C12 S13 C14 102.02(16) y
C15 C14 S13 111.5(2) y
C16 C15 C20 118.7(3) ?
C16 C15 C14 120.9(3) ?
C20 C15 C14 120.3(3) y
C17 C16 C15 119.4(3) ?
C18 C17 C16 121.3(3) ?
C17 C18 C19 120.0(3) ?
C20 C19 C18 118.5(3) ?
C20 C19 C1 120.4(3) y
C18 C19 C1 121.0(3) ?
C19 C20 C15 121.9(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C19 1.509(5) y
C1 S2 1.809(4) y
S2 C3 1.832(4) y
C3 C4 1.493(5) y
C4 C11 1.390(5) y
C4 C5 1.399(5) ?
C5 C6 1.383(5) ?
C6 C6' 1.427(5) ?
C6' C7 1.410(5) ?
C6' C10' 1.427(5) ?
C7 C8 1.355(6) ?
C8 C9 1.405(5) ?
C9 C10 1.369(5) ?
C10 C10' 1.452(5) y
C10 C12 1.487(5) y
C10' C11 1.395(5) y
C12 S13 1.828(3) y
S13 C14 1.830(4) y
C14 C15 1.511(5) y
C15 C16 1.388(5) ?
C15 C20 1.391(5) y
C16 C17 1.387(5) ?
C17 C18 1.375(5) ?
C18 C19 1.390(5) ?
C19 C20 1.384(5) 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 -66.4(3) y
C1 S2 C3 C4 124.1(3) y
S2 C3 C4 C11 -72.3(4) y
S2 C3 C4 C5 109.0(3) ?
C11 C4 C5 C6 -2.9(5) ?
C3 C4 C5 C6 175.9(3) ?
C4 C5 C6 C6' 1.9(5) ?
C5 C6 C6' C7 -179.1(3) ?
C5 C6 C6' C10' 0.2(5) ?
C10' C6' C7 C8 0.1(5) ?
C6 C6' C7 C8 179.4(3) ?
C6' C7 C8 C9 1.6(5) ?
C7 C8 C9 C10 -1.6(5) ?
C8 C9 C10 C10' -0.1(5) ?
C8 C9 C10 C12 177.9(3) ?
C7 C6' C10' C11 177.9(3) ?
C6 C6' C10' C11 -1.4(4) ?
C7 C6' C10' C10 -1.7(4) ?
C6 C6' C10' C10 178.9(3) ?
C9 C10 C10' C11 -177.9(3) ?
C12 C10 C10' C11 4.1(5) y
C9 C10 C10' C6' 1.8(4) ?
C12 C10 C10' C6' -176.3(3) ?
C5 C4 C11 C10' 1.6(5) ?
C3 C4 C11 C10' -177.2(3) y
C6' C10' C11 C4 0.5(5) ?
C10 C10' C11 C4 -179.9(3) y
C9 C10 C12 S13 -100.3(3) ?
C10' C10 C12 S13 77.7(3) y
C10 C12 S13 C14 -157.0(2) y
C12 S13 C14 C15 57.7(3) y
S13 C14 C15 C16 -107.3(3) ?
S13 C14 C15 C20 69.0(4) y
C20 C15 C16 C17 -1.7(5) ?
C14 C15 C16 C17 174.7(3) ?
C15 C16 C17 C18 -0.6(5) ?
C16 C17 C18 C19 1.7(5) ?
C17 C18 C19 C20 -0.4(5) ?
C17 C18 C19 C1 -178.6(3) ?
S2 C1 C19 C20 -55.8(4) y
S2 C1 C19 C18 122.3(3) ?
C18 C19 C20 C15 -1.9(5) ?
C1 C19 C20 C15 176.3(3) y
C16 C15 C20 C19 3.0(5) ?
C14 C15 C20 C19 -173.4(3) y