#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023740.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_4023740
loop_
_publ_author_name
'Daniel B. Werz'
'Felix R. Fischer'
'Stefan C. Kornmayer'
'Frank Rominger'
'Rolf Gleiter'
_publ_contact_author_address
;
        Organisch-Chemisches Institut
        Universität Heidelberg
        Im Neuenheimer Feld 270
        D-69120 Heidelberg
        Germany
;
_publ_contact_author_email       rolf.gleiter@oci.uni-heidelberg.de
_publ_contact_author_fax         '049 6221 54- 4205'
_publ_contact_author_name        'Gleiter, Rolf'
_publ_contact_author_phone       '049 6221 54- 8400'
_publ_section_title
;
 Macrocyclic Cyclophanes with Two and Three
 α,ω-Dichalcogena-1,4-diethynylaryl Units:
 Syntheses and Structural Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8021
_journal_page_last               8029
_journal_paper_doi               10.1021/jo801378p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C54 H76 S4'
_chemical_formula_weight         853.39
_chemical_name_systematic
;
 ?
;
_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                65.4210(10)
_cell_angle_beta                 86.628(2)
_cell_angle_gamma                75.3200(10)
_cell_formula_units_Z            1
_cell_length_a                   8.2206(3)
_cell_length_b                   12.8156(4)
_cell_length_c                   13.7297(5)
_cell_measurement_temperature    200(2)
_cell_volume                     1270.66(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13289
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0552
_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)+(0.0743P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                2827
_reflns_number_total             5785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801378p_si_002_03.cif
_cod_data_source_block           dwe105_(in_paper_6)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023740
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 1.09148(10) -0.41064(6) 1.37830(5) 0.0601(3) Uani 1 1 d . . .
S2 S 0.71964(9) 0.11213(6) 0.48541(5) 0.0567(2) Uani 1 1 d . . .
C2 C 1.0404(3) -0.3286(2) 1.24592(19) 0.0458(6) Uani 1 1 d . . .
C3 C 1.0006(3) -0.2748(2) 1.15308(19) 0.0440(6) Uani 1 1 d . . .
C4 C 0.9503(3) -0.2085(2) 1.04162(17) 0.0413(6) Uani 1 1 d . . .
C5 C 1.0095(3) -0.2587(2) 0.96891(18) 0.0438(6) Uani 1 1 d . . .
H5 H 1.0825 -0.3362 0.9947 0.053 Uiso 1 1 calc R . .
C6 C 0.9643(3) -0.1979(2) 0.86045(18) 0.0412(6) Uani 1 1 d . . .
C7 C 1.0290(3) -0.2517(2) 0.78202(18) 0.0507(7) Uani 1 1 d . . .
H7A H 1.0915 -0.1993 0.7280 0.061 Uiso 1 1 calc R . .
H7B H 0.9309 -0.2521 0.7438 0.061 Uiso 1 1 calc R . .
C8 C 1.1432(3) -0.3771(2) 0.82918(18) 0.0454(6) Uani 1 1 d . . .
H8A H 1.0819 -0.4309 0.8828 0.054 Uiso 1 1 calc R . .
H8B H 1.2431 -0.3779 0.8666 0.054 Uiso 1 1 calc R . .
C9 C 1.2010(3) -0.4230(2) 0.74280(19) 0.0502(7) Uani 1 1 d . . .
H9A H 1.1012 -0.4276 0.7093 0.060 Uiso 1 1 calc R . .
H9B H 1.2538 -0.3655 0.6863 0.060 Uiso 1 1 calc R . .
C10 C 1.3240(3) -0.5425(2) 0.78530(19) 0.0493(7) Uani 1 1 d . . .
H10A H 1.2697 -0.6004 0.8402 0.059 Uiso 1 1 calc R . .
H10B H 1.4218 -0.5384 0.8211 0.059 Uiso 1 1 calc R . .
C11 C 1.3875(4) -0.5880(2) 0.6993(2) 0.0627(8) Uani 1 1 d . . .
H11A H 1.2898 -0.5894 0.6614 0.075 Uiso 1 1 calc R . .
H11B H 1.4468 -0.5324 0.6460 0.075 Uiso 1 1 calc R . .
C12 C 1.5050(4) -0.7103(3) 0.7454(2) 0.0736(9) Uani 1 1 d . . .
H12A H 1.6080 -0.7076 0.7757 0.110 Uiso 1 1 calc R . .
H12B H 1.5335 -0.7383 0.6886 0.110 Uiso 1 1 calc R . .
H12C H 1.4499 -0.7646 0.8018 0.110 Uiso 1 1 calc R . .
C13 C 0.3215(4) 0.4087(3) 1.1440(3) 0.0756(9) Uani 1 1 d . . .
H13A H 0.3800 0.4652 1.0931 0.113 Uiso 1 1 calc R . .
H13B H 0.2914 0.4290 1.2053 0.113 Uiso 1 1 calc R . .
H13C H 0.2190 0.4123 1.1085 0.113 Uiso 1 1 calc R . .
C14 C 0.4357(3) 0.2847(2) 1.1830(2) 0.0577(7) Uani 1 1 d . . .
H14A H 0.3761 0.2285 1.2351 0.069 Uiso 1 1 calc R . .
H14B H 0.5368 0.2813 1.2211 0.069 Uiso 1 1 calc R . .
C15 C 0.4913(3) 0.2451(2) 1.09374(19) 0.0484(7) Uani 1 1 d . . .
H15A H 0.3901 0.2483 1.0558 0.058 Uiso 1 1 calc R . .
H15B H 0.5506 0.3014 1.0415 0.058 Uiso 1 1 calc R . .
C16 C 0.6057(3) 0.1213(2) 1.13238(19) 0.0492(7) Uani 1 1 d . . .
H16A H 0.5466 0.0650 1.1848 0.059 Uiso 1 1 calc R . .
H16B H 0.7072 0.1182 1.1700 0.059 Uiso 1 1 calc R . .
C17 C 0.6602(3) 0.0819(2) 1.04266(18) 0.0473(7) Uani 1 1 d . . .
H17A H 0.7159 0.1394 0.9886 0.057 Uiso 1 1 calc R . .
H17B H 0.5596 0.0811 1.0070 0.057 Uiso 1 1 calc R . .
C18 C 0.7807(3) -0.0409(2) 1.08503(18) 0.0497(7) Uani 1 1 d . . .
H18A H 0.8805 -0.0378 1.1197 0.060 Uiso 1 1 calc R . .
H18B H 0.7247 -0.0960 1.1416 0.060 Uiso 1 1 calc R . .
C19 C 0.8423(3) -0.0939(2) 1.00530(18) 0.0412(6) Uani 1 1 d . . .
C20 C 0.7977(3) -0.0330(2) 0.89619(18) 0.0446(6) Uani 1 1 d . . .
H20 H 0.7253 0.0447 0.8700 0.054 Uiso 1 1 calc R . .
C21 C 0.8570(3) -0.0835(2) 0.82429(17) 0.0408(6) Uani 1 1 d . . .
C22 C 0.8063(3) -0.0172(2) 0.7125(2) 0.0463(6) Uani 1 1 d . . .
C23 C 0.7657(3) 0.0380(2) 0.61852(19) 0.0468(6) Uani 1 1 d . . .
C25 C 0.5233(3) 0.2180(2) 0.48049(19) 0.0571(8) Uani 1 1 d . . .
H25A H 0.5443 0.2703 0.5122 0.068 Uiso 1 1 calc R . .
H25B H 0.4852 0.2682 0.4044 0.068 Uiso 1 1 calc R . .
C26 C 0.3840(3) 0.1634(2) 0.5380(2) 0.0601(8) Uani 1 1 d . . .
H26A H 0.4183 0.1172 0.6151 0.072 Uiso 1 1 calc R . .
H26B H 0.3658 0.1080 0.5091 0.072 Uiso 1 1 calc R . .
C27 C 0.2192(4) 0.2564(3) 0.5260(2) 0.0641(8) Uani 1 1 d . . .
H27A H 0.2407 0.3161 0.5483 0.077 Uiso 1 1 calc R . .
H27B H 0.1804 0.2976 0.4494 0.077 Uiso 1 1 calc R . .
C28 C 0.0838(4) 0.2075(3) 0.5892(2) 0.0662(8) Uani 1 1 d . . .
H28A H 0.1215 0.1693 0.6660 0.079 Uiso 1 1 calc R . .
H28B H 0.0671 0.1449 0.5693 0.079 Uiso 1 1 calc R . .
C29 C 1.0836(4) -0.2956(3) 1.4242(2) 0.0639(8) Uani 1 1 d . . .
H29A H 1.1199 -0.3345 1.5012 0.077 Uiso 1 1 calc R . .
H29B H 1.1670 -0.2512 1.3854 0.077 Uiso 1 1 calc R . .
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 C29 101.05(12) . . ?
C23 S2 C25 101.76(12) . . ?
C3 C2 S1 176.8(2) . . ?
C2 C3 C4 178.9(3) . . ?
C5 C4 C19 120.2(2) . . ?
C5 C4 C3 119.5(2) . . ?
C19 C4 C3 120.3(2) . . ?
C6 C5 C4 121.6(2) . . ?
C5 C6 C21 118.2(2) . . ?
C5 C6 C7 121.6(2) . . ?
C21 C6 C7 120.3(2) . . ?
C6 C7 C8 116.4(2) . . ?
C7 C8 C9 112.1(2) . . ?
C10 C9 C8 113.4(2) . . ?
C9 C10 C11 114.1(2) . . ?
C12 C11 C10 112.6(2) . . ?
C13 C14 C15 113.6(2) . . ?
C16 C15 C14 113.7(2) . . ?
C15 C16 C17 113.5(2) . . ?
C16 C17 C18 111.43(19) . . ?
C19 C18 C17 117.6(2) . . ?
C20 C19 C4 118.0(2) . . ?
C20 C19 C18 122.6(2) . . ?
C4 C19 C18 119.4(2) . . ?
C19 C20 C21 121.5(2) . . ?
C20 C21 C6 120.6(2) . . ?
C20 C21 C22 119.3(2) . . ?
C6 C21 C22 120.2(2) . . ?
C23 C22 C21 179.2(3) . . ?
C22 C23 S2 176.9(2) . . ?
C26 C25 S2 114.58(19) . . ?
C25 C26 C27 112.2(2) . . ?
C28 C27 C26 113.9(2) . . ?
C27 C28 C29 115.7(2) . 2_657 ?
C28 C29 S1 116.9(2) 2_657 . ?
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 1.692(2) . ?
S1 C29 1.815(3) . ?
S2 C23 1.685(2) . ?
S2 C25 1.810(3) . ?
C2 C3 1.188(3) . ?
C3 C4 1.432(3) . ?
C4 C5 1.402(3) . ?
C4 C19 1.406(3) . ?
C5 C6 1.384(3) . ?
C6 C21 1.402(3) . ?
C6 C7 1.510(3) . ?
C7 C8 1.525(3) . ?
C8 C9 1.534(3) . ?
C9 C10 1.499(3) . ?
C10 C11 1.534(3) . ?
C11 C12 1.507(4) . ?
C13 C14 1.513(3) . ?
C14 C15 1.517(3) . ?
C15 C16 1.511(3) . ?
C16 C17 1.520(3) . ?
C17 C18 1.521(3) . ?
C18 C19 1.515(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.436(3) . ?
C22 C23 1.203(3) . ?
C25 C26 1.505(4) . ?
C26 C27 1.526(4) . ?
C27 C28 1.474(4) . ?
C28 C29 1.507(4) 2_657 ?
C29 C28 1.507(4) 2_657 ?
