#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023741.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_4023741
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            'C38 H44 S4'
_chemical_formula_weight         628.97
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.261(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1593(18)
_cell_length_b                   9.1700(13)
_cell_length_c                   15.565(2)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.80
_cell_volume                     1712.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'ω 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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17286
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.9254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0493
_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)+(0.0487P)²+0.9230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                3899
_reflns_number_total             4258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801378p_si_002_04.cif
_cod_data_source_block           ff1_(in_paper_7(3))
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023741
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.97491(4) -0.16013(5) 0.28250(3) 0.02083(13) Uani 1 1 d . . .
S2 S 0.12117(4) 0.38270(5) 0.03497(3) 0.02089(13) Uani 1 1 d . . .
C1 C 0.66108(14) 0.07107(18) 0.18143(12) 0.0157(3) Uani 1 1 d . . .
C2 C 0.60693(14) 0.12282(18) 0.08818(12) 0.0154(3) Uani 1 1 d . . .
C3 C 0.50433(14) 0.19008(18) 0.06259(12) 0.0158(3) Uani 1 1 d . . .
H3 H 0.4673 0.2270 0.0004 0.019 Uiso 1 1 calc R . .
C4 C 0.45327(14) 0.20551(18) 0.12537(12) 0.0153(3) Uani 1 1 d . . .
C5 C 0.50721(14) 0.15379(18) 0.21842(12) 0.0155(3) Uani 1 1 d . . .
C6 C 0.61046(14) 0.08831(18) 0.24464(12) 0.0163(3) Uani 1 1 d . . .
H6 H 0.6483 0.0539 0.3074 0.020 Uiso 1 1 calc R . .
C7 C 0.76656(14) -0.00276(19) 0.21275(12) 0.0173(3) Uani 1 1 d . . .
C8 C 0.85364(14) -0.0664(2) 0.24000(12) 0.0181(3) Uani 1 1 d . . .
C9 C 1.02941(15) -0.1096(2) 0.19596(14) 0.0226(4) Uani 1 1 d . . .
H9A H 1.0384 -0.0023 0.1969 0.027 Uiso 1 1 calc R . .
H9B H 1.1041 -0.1537 0.2147 0.027 Uiso 1 1 calc R . .
C10 C 0.04405(15) 0.15705(19) -0.09597(13) 0.0185(3) Uani 1 1 d . . .
H10A H 0.0125 0.1189 -0.0526 0.022 Uiso 1 1 calc R . .
H10B H 0.1193 0.1145 -0.0771 0.022 Uiso 1 1 calc R . .
C11 C 0.05381(14) 0.32194(19) -0.08661(12) 0.0168(3) Uani 1 1 d . . .
H11A H -0.0217 0.3652 -0.1159 0.020 Uiso 1 1 calc R . .
H11B H 0.0969 0.3581 -0.1215 0.020 Uiso 1 1 calc R . .
C12 C 0.25087(14) 0.31580(19) 0.06611(12) 0.0173(3) Uani 1 1 d . . .
C13 C 0.34424(14) 0.26922(19) 0.09292(12) 0.0171(3) Uani 1 1 d . . .
C14 C 0.65846(14) 0.10604(19) 0.01825(12) 0.0163(3) Uani 1 1 d . . .
H14A H 0.5987 0.1094 -0.0463 0.020 Uiso 1 1 calc R . .
H14B H 0.6946 0.0092 0.0271 0.020 Uiso 1 1 calc R . .
C15 C 0.74478(16) 0.2240(2) 0.02773(14) 0.0222(4) Uani 1 1 d . . .
H15A H 0.7081 0.3207 0.0157 0.027 Uiso 1 1 calc R . .
H15B H 0.8031 0.2238 0.0930 0.027 Uiso 1 1 calc R . .
C16 C 0.79892(17) 0.1997(2) -0.04083(16) 0.0274(4) Uani 1 1 d . . .
H16A H 0.8327 0.1024 -0.0308 0.041 Uiso 1 1 calc R . .
H16B H 0.8566 0.2736 -0.0302 0.041 Uiso 1 1 calc R . .
H16C H 0.7423 0.2074 -0.1056 0.041 Uiso 1 1 calc R . .
C17 C 0.45434(14) 0.16507(19) 0.28796(12) 0.0171(3) Uani 1 1 d . . .
H17A H 0.4208 0.2631 0.2827 0.021 Uiso 1 1 calc R . .
H17B H 0.5132 0.1550 0.3526 0.021 Uiso 1 1 calc R . .
C18 C 0.36446(15) 0.0501(2) 0.27292(13) 0.0199(4) Uani 1 1 d . . .
H18A H 0.3036 0.0625 0.2094 0.024 Uiso 1 1 calc R . .
H18B H 0.3968 -0.0483 0.2760 0.024 Uiso 1 1 calc R . .
C19 C 0.31680(16) 0.0620(2) 0.34695(14) 0.0259(4) Uani 1 1 d . . .
H19A H 0.3763 0.0458 0.4097 0.039 Uiso 1 1 calc R . .
H19B H 0.2584 -0.0115 0.3345 0.039 Uiso 1 1 calc R . .
H19C H 0.2851 0.1595 0.3442 0.039 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
C8 S1 C9 100.14(9) . . ?
C12 S2 C11 101.00(8) . . ?
C6 C1 C2 119.88(15) . . ?
C6 C1 C7 119.02(15) . . ?
C2 C1 C7 121.09(16) . . ?
C3 C2 C1 117.78(16) . . ?
C3 C2 C14 120.79(15) . . ?
C1 C2 C14 121.43(15) . . ?
C2 C3 C4 122.28(16) . . ?
C3 C4 C5 119.97(15) . . ?
C3 C4 C13 119.47(15) . . ?
C5 C4 C13 120.52(16) . . ?
C6 C5 C4 117.92(16) . . ?
C6 C5 C17 120.21(16) . . ?
C4 C5 C17 121.85(15) . . ?
C5 C6 C1 122.16(16) . . ?
C8 C7 C1 178.49(19) . . ?
C7 C8 S1 177.21(17) . . ?
C10 C9 S1 113.90(13) 3_655 . ?
C11 C10 C9 112.11(15) . 3_655 ?
C10 C11 S2 113.02(12) . . ?
C13 C12 S2 176.73(17) . . ?
C12 C13 C4 176.71(19) . . ?
C2 C14 C15 113.22(14) . . ?
C16 C15 C14 111.81(15) . . ?
C5 C17 C18 113.44(14) . . ?
C19 C18 C17 111.53(15) . . ?
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 C8 1.6896(18) . ?
S1 C9 1.827(2) . ?
S2 C12 1.6865(18) . ?
S2 C11 1.8162(18) . ?
C1 C6 1.405(2) . ?
C1 C2 1.411(2) . ?
C1 C7 1.438(2) . ?
C2 C3 1.386(2) . ?
C2 C14 1.508(2) . ?
C3 C4 1.402(2) . ?
C4 C5 1.408(2) . ?
C4 C13 1.435(2) . ?
C5 C6 1.385(2) . ?
C5 C17 1.512(2) . ?
C7 C8 1.198(2) . ?
C9 C10 1.520(3) 3_655 ?
C10 C11 1.519(2) . ?
C10 C9 1.520(3) 3_655 ?
C12 C13 1.202(2) . ?
C14 C15 1.531(2) . ?
C15 C16 1.523(3) . ?
C17 C18 1.529(2) . ?
C18 C19 1.525(3) . ?
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
C6 C1 C2 C3 0.2(2) . . . . ?
C7 C1 C2 C3 178.62(16) . . . . ?
C6 C1 C2 C14 -179.86(15) . . . . ?
C7 C1 C2 C14 -1.4(2) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C14 C2 C3 C4 179.01(15) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C13 -176.66(16) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C13 C4 C5 C6 177.55(16) . . . . ?
C3 C4 C5 C17 -178.65(15) . . . . ?
C13 C4 C5 C17 -1.0(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C17 C5 C6 C1 177.83(15) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C7 C1 C6 C5 -177.75(16) . . . . ?
C6 C1 C7 C8 38(8) . . . . ?
C2 C1 C7 C8 -141(8) . . . . ?
C1 C7 C8 S1 -15(11) . . . . ?
C9 S1 C8 C7 175(4) . . . . ?
C8 S1 C9 C10 -61.63(15) . . . 3_655 ?
C9 C10 C11 S2 170.26(12) 3_655 . . . ?
C12 S2 C11 C10 65.60(14) . . . . ?
C11 S2 C12 C13 -164(3) . . . . ?
S2 C12 C13 C4 87(4) . . . . ?
C3 C4 C13 C12 110(3) . . . . ?
C5 C4 C13 C12 -68(3) . . . . ?
C3 C2 C14 C15 97.89(19) . . . . ?
C1 C2 C14 C15 -82.1(2) . . . . ?
C2 C14 C15 C16 177.37(16) . . . . ?
C6 C5 C17 C18 -100.86(19) . . . . ?
C4 C5 C17 C18 77.7(2) . . . . ?
C5 C17 C18 C19 177.79(15) . . . . ?
