#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:38:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180230 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/16/7111698.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111698
loop_
_publ_author_name
'Lee, Gon-Ann'
'Wang, Wen-Chieh'
'Shieh, Minghuey'
'Kuo, Ting-Shen'
_publ_section_title
;
 A novel synthesis of calix[4]thiophenes and calix[4]furans
;
_journal_issue                   27
_journal_name_full               'Chemical Communications'
_journal_page_first              5009
_journal_page_last               5011
_journal_paper_doi               10.1039/c0cc00437e
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C44 H64 S4'
_chemical_formula_sum            'C44 H64 S4'
_chemical_formula_weight         721.19
_chemical_melting_point          342.0(5)
_chemical_name_common            octapropyl
_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                104.2410(10)
_cell_angle_beta                 95.4480(10)
_cell_angle_gamma                97.4850(10)
_cell_formula_units_Z            1
_cell_length_a                   8.2550(2)
_cell_length_b                   10.5082(2)
_cell_length_c                   12.4009(3)
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     1024.71(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12008
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  1.017
_exptl_absorpt_correction_T_min  0.7979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0388
_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)+(0.0548P)²+0.3078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                3008
_reflns_number_total             3596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00437Esup1.cif
_cod_data_source_block           9239
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '341.5-342.5' was changed to
'342.0(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               7111698
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
S1 S 0.27436(7) 0.35263(5) -0.02537(4) 0.02580(16) Uani 1 1 d .
S2 S 0.46960(6) 0.59496(5) 0.23406(4) 0.02622(16) Uani 1 1 d .
C1 C 0.3035(2) 0.19286(19) -0.09043(16) 0.0222(4) Uani 1 1 d .
C2 C 0.2749(3) 0.1122(2) -0.02198(17) 0.0310(5) Uani 1 1 d .
H2 H 0.2854 0.0207 -0.0416 0.037 Uiso 1 1 calc R
C3 C 0.2277(3) 0.1779(2) 0.08231(18) 0.0313(5) Uani 1 1 d .
H3 H 0.2032 0.1342 0.1387 0.038 Uiso 1 1 calc R
C4 C 0.2208(2) 0.3092(2) 0.09359(16) 0.0227(4) Uani 1 1 d .
C5 C 0.1716(2) 0.41344(19) 0.18948(16) 0.0216(4) Uani 1 1 d .
C6 C 0.2238(3) 0.3806(2) 0.30165(16) 0.0243(5) Uani 1 1 d .
H6A H 0.1686 0.2899 0.2978 0.029 Uiso 1 1 calc R
H6B H 0.3440 0.3796 0.3091 0.029 Uiso 1 1 calc R
C7 C 0.1851(3) 0.4754(2) 0.40701(17) 0.0358(5) Uani 1 1 d .
H7A H 0.0643 0.4725 0.4032 0.043 Uiso 1 1 calc R
H7B H 0.2355 0.5673 0.4103 0.043 Uiso 1 1 calc R
C8 C 0.2496(3) 0.4397(3) 0.51277(19) 0.0483(7) Uani 1 1 d .
H8A H 0.2233 0.5030 0.5786 0.073 Uiso 1 1 calc R
H8B H 0.3694 0.4435 0.5172 0.073 Uiso 1 1 calc R
H8C H 0.1978 0.3496 0.5107 0.073 Uiso 1 1 calc R
C9 C -0.0169(2) 0.4137(2) 0.16973(17) 0.0252(5) Uani 1 1 d .
H9A H -0.0446 0.4857 0.2298 0.030 Uiso 1 1 calc R
H9B H -0.0428 0.4361 0.0977 0.030 Uiso 1 1 calc R
C10 C -0.1286(3) 0.2855(2) 0.1666(2) 0.0381(6) Uani 1 1 d .
H10A H -0.1053 0.2127 0.1053 0.046 Uiso 1 1 calc R
H10B H -0.1051 0.2616 0.2383 0.046 Uiso 1 1 calc R
C11 C -0.3093(3) 0.2999(2) 0.1482(2) 0.0369(6) Uani 1 1 d .
H11A H -0.3783 0.2161 0.1467 0.055 Uiso 1 1 calc R
H11B H -0.3332 0.3219 0.0766 0.055 Uiso 1 1 calc R
H11C H -0.3329 0.3711 0.2095 0.055 Uiso 1 1 calc R
C12 C 0.2596(2) 0.5502(2) 0.18955(15) 0.0214(4) Uani 1 1 d .
C13 C 0.2019(3) 0.6487(2) 0.15198(17) 0.0256(5) Uani 1 1 d .
H13 H 0.0894 0.6446 0.1246 0.031 Uiso 1 1 calc R
C14 C 0.3252(2) 0.7584(2) 0.15743(17) 0.0276(5) Uani 1 1 d .
H14 H 0.3027 0.8345 0.1339 0.033 Uiso 1 1 calc R
C15 C 0.4782(2) 0.74503(19) 0.19930(15) 0.0219(4) Uani 1 1 d .
C16 C 0.6420(2) 0.8361(2) 0.20705(16) 0.0226(4) Uani 1 1 d .
C17 C 0.6151(3) 0.9826(2) 0.24513(16) 0.0257(5) Uani 1 1 d .
H17A H 0.7177 1.0409 0.2414 0.031 Uiso 1 1 calc R
H17B H 0.5272 0.9974 0.1916 0.031 Uiso 1 1 calc R
C18 C 0.5680(3) 1.0242(2) 0.36327(18) 0.0327(5) Uani 1 1 d .
H18A H 0.4687 0.9633 0.3687 0.039 Uiso 1 1 calc R
H18B H 0.6587 1.0151 0.4177 0.039 Uiso 1 1 calc R
C19 C 0.5338(5) 1.1647(3) 0.3944(2) 0.0683(10) Uani 1 1 d .
H19A H 0.5027 1.1857 0.4703 0.102 Uiso 1 1 calc R
H19B H 0.4435 1.1742 0.3411 0.102 Uiso 1 1 calc R
H19C H 0.6330 1.2258 0.3919 0.102 Uiso 1 1 calc R
C20 C 0.7751(2) 0.8064(2) 0.29075(17) 0.0269(5) Uani 1 1 d .
H20A H 0.7351 0.8193 0.3649 0.032 Uiso 1 1 calc R
H20B H 0.7876 0.7117 0.2647 0.032 Uiso 1 1 calc R
C21 C 0.9439(3) 0.8913(2) 0.30572(19) 0.0365(6) Uani 1 1 d .
H21A H 0.9332 0.9863 0.3327 0.044 Uiso 1 1 calc R
H21B H 0.9859 0.8783 0.2322 0.044 Uiso 1 1 calc R
C22 C 1.0669(3) 0.8560(3) 0.3890(2) 0.0482(7) Uani 1 1 d .
H22A H 1.1734 0.9133 0.3972 0.072 Uiso 1 1 calc R
H22B H 1.0804 0.7628 0.3613 0.072 Uiso 1 1 calc R
H22C H 1.0260 0.8693 0.4619 0.072 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
C4 S1 C1 93.10(9) . .
C15 S2 C12 93.25(9) . .
C2 C1 C16 130.51(18) . 2_665
C2 C1 S1 109.95(15) . .
C16 C1 S1 119.53(15) 2_665 .
C1 C2 C3 113.50(19) . .
C1 C2 H2 123.2 . .
C3 C2 H2 123.2 . .
C4 C3 C2 113.73(19) . .
C4 C3 H3 123.1 . .
C2 C3 H3 123.1 . .
C3 C4 C5 130.46(18) . .
C3 C4 S1 109.71(15) . .
C5 C4 S1 119.81(14) . .
C12 C5 C4 108.75(16) . .
C12 C5 C6 110.24(16) . .
C4 C5 C6 108.49(16) . .
C12 C5 C9 108.07(16) . .
C4 C5 C9 109.58(15) . .
C6 C5 C9 111.67(16) . .
C7 C6 C5 115.74(17) . .
C7 C6 H6A 108.3 . .
C5 C6 H6A 108.3 . .
C7 C6 H6B 108.3 . .
C5 C6 H6B 108.3 . .
H6A C6 H6B 107.4 . .
C6 C7 C8 111.78(19) . .
C6 C7 H7A 109.3 . .
C8 C7 H7A 109.3 . .
C6 C7 H7B 109.3 . .
C8 C7 H7B 109.3 . .
H7A C7 H7B 107.9 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C5 116.69(17) . .
C10 C9 H9A 108.1 . .
C5 C9 H9A 108.1 . .
C10 C9 H9B 108.1 . .
C5 C9 H9B 108.1 . .
H9A C9 H9B 107.3 . .
C11 C10 C9 111.22(19) . .
C11 C10 H10A 109.4 . .
C9 C10 H10A 109.4 . .
C11 C10 H10B 109.4 . .
C9 C10 H10B 109.4 . .
H10A C10 H10B 108.0 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C5 130.00(18) . .
C13 C12 S2 109.52(15) . .
C5 C12 S2 120.33(14) . .
C12 C13 C14 113.73(18) . .
C12 C13 H13 123.1 . .
C14 C13 H13 123.1 . .
C15 C14 C13 114.01(19) . .
C15 C14 H14 123.0 . .
C13 C14 H14 123.0 . .
C14 C15 C16 128.47(19) . .
C14 C15 S2 109.48(15) . .
C16 C15 S2 121.81(14) . .
C1 C16 C15 107.55(15) 2_665 .
C1 C16 C17 110.26(16) 2_665 .
C15 C16 C17 108.93(16) . .
C1 C16 C20 109.14(16) 2_665 .
C15 C16 C20 110.27(16) . .
C17 C16 C20 110.65(16) . .
C18 C17 C16 114.65(17) . .
C18 C17 H17A 108.6 . .
C16 C17 H17A 108.6 . .
C18 C17 H17B 108.6 . .
C16 C17 H17B 108.6 . .
H17A C17 H17B 107.6 . .
C19 C18 C17 112.9(2) . .
C19 C18 H18A 109.0 . .
C17 C18 H18A 109.0 . .
C19 C18 H18B 109.0 . .
C17 C18 H18B 109.0 . .
H18A C18 H18B 107.8 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 C16 115.10(18) . .
C21 C20 H20A 108.5 . .
C16 C20 H20A 108.5 . .
C21 C20 H20B 108.5 . .
C16 C20 H20B 108.5 . .
H20A C20 H20B 107.5 . .
C20 C21 C22 111.8(2) . .
C20 C21 H21A 109.3 . .
C22 C21 H21A 109.3 . .
C20 C21 H21B 109.3 . .
C22 C21 H21B 109.3 . .
H21A C21 H21B 107.9 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.727(2) .
S1 C1 1.733(2) .
S2 C15 1.729(2) .
S2 C12 1.7344(19) .
C1 C2 1.354(3) .
C1 C16 1.526(3) 2_665
C2 C3 1.424(3) .
C2 H2 0.9500 .
C3 C4 1.361(3) .
C3 H3 0.9500 .
C4 C5 1.532(3) .
C5 C12 1.523(3) .
C5 C6 1.549(3) .
C5 C9 1.552(3) .
C6 C7 1.524(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.518(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.520(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.520(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.356(3) .
C13 C14 1.419(3) .
C13 H13 0.9500 .
C14 C15 1.358(3) .
C14 H14 0.9500 .
C15 C16 1.532(3) .
C16 C1 1.526(3) 2_665
C16 C17 1.547(3) .
C16 C20 1.554(3) .
C17 C18 1.525(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.502(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C21 1.523(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.524(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
