#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:05:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178420 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024161.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_4024161
loop_
_publ_author_name
'Hana Dvořáková'
'Jan Lang'
'Jiří Vlach'
'Jan Sýkora'
'Michal Čajan'
'Michal Himl'
'Michaela Pojarová'
'Ivan Stibor'
'Pavel Lhoták'
_publ_section_title
;
 Partially O-Alkylated Thiacalix[4]arenes: Synthesis, Molecular and
 Crystal Structures, Conformational Behavior
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7157
_journal_page_last               7166
_journal_paper_doi               10.1021/jo070927i
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C14 H12 O2 S2'
_chemical_formula_sum            'C14 H12 O2 S2'
_chemical_formula_weight         276.38
_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
_audit_creation_date             07-04-24
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                66.037(5)
_cell_angle_beta                 74.034(5)
_cell_angle_gamma                62.740(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9805(4)
_cell_length_b                   9.2539(5)
_cell_length_c                   9.8518(7)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    293
_cell_measurement_theta_max      39
_cell_measurement_theta_min      35
_cell_volume                     661.06(7)
_computing_cell_refinement       'CAD4 Express, (Straver, 1992)'
_computing_data_collection       'CAD4 Express, (Straver, 1992)'
_computing_data_reduction        'RC93 (Watkin, Prout & Lilley, 1994)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5115
_diffrn_reflns_theta_full        66.910
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_min         4.942
_diffrn_standards_decay_%        1.50
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.574
_exptl_absorpt_correction_T_max  0.8363
_exptl_absorpt_correction_T_min  0.3422
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.79
_refine_diff_density_min         -0.86
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0826
_refine_ls_shift/su_max          0.000814
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.52 11.1 8.06 2.60 0.627 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0782
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0744
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -9
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2161
_reflns_number_total             2404
_reflns_threshold_expression     I>1.96u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          4.009(18)
_oxford_structure_analysis_title 'DIETHOXY.INI 23/8/2000'
_cod_data_source_file            jo070927i-File006.cif
_cod_data_source_block           CRYSTALS_cif
_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_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4024161
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S2 S 1.49635(7) -0.16402(9) -0.17928(7) 0.0578 1.0000 Uani . . . . . .
S20 S 0.89822(8) 0.39587(7) -0.33277(6) 0.0516 1.0000 Uani . . . . . .
O29 O 1.1676(2) 0.1256(2) -0.12516(17) 0.0471 1.0000 Uani . . . . . .
O30 O 1.17723(18) -0.24380(18) 0.00140(16) 0.0422 1.0000 Uani . . . . . .
C1 C 1.3216(3) -0.0418(3) -0.2843(2) 0.0463 1.0000 Uani . . . . . .
C3 C 1.4273(3) -0.2154(3) 0.0140(3) 0.0452 1.0000 Uani . . . . . .
C4 C 1.5342(3) -0.2253(3) 0.1012(3) 0.0541 1.0000 Uani . . . . . .
C5 C 1.5113(3) -0.2859(4) 0.2541(3) 0.0585 1.0000 Uani . . . . . .
C6 C 1.3783(3) -0.3365(3) 0.3240(3) 0.0568 1.0000 Uani . . . . . .
C7 C 1.2683(3) -0.3247(3) 0.2394(3) 0.0448 1.0000 Uani . . . . . .
C21 C 1.0628(3) 0.2036(3) -0.3575(2) 0.0459 1.0000 Uani . . . . . .
C22 C 1.0824(4) 0.1674(4) -0.4871(3) 0.0617 1.0000 Uani . . . . . .
C23 C 1.2169(4) 0.0269(4) -0.5143(3) 0.0680 1.0000 Uani . . . . . .
C24 C 1.3366(4) -0.0756(4) -0.4145(3) 0.0611 1.0000 Uani . . . . . .
C25 C 1.1807(3) 0.0980(3) -0.2541(2) 0.0410 1.0000 Uani . . . . . .
C26 C 1.2917(2) -0.2640(2) 0.0847(2) 0.0394 1.0000 Uani . . . . . .
C33 C 1.2249(3) -0.3860(3) -0.0510(3) 0.0530 1.0000 Uani . . . . . .
C34 C 1.0909(4) -0.3362(4) -0.1444(3) 0.0685 1.0000 Uani . . . . . .
H41 H 1.616(5) -0.175(5) 0.062(4) 0.082(10) 1.0000 Uiso . . . . . .
H51 H 1.574(4) -0.283(4) 0.312(4) 0.065(8) 1.0000 Uiso . . . . . .
H61 H 1.354(5) -0.375(5) 0.434(5) 0.087(11) 1.0000 Uiso . . . . . .
H221 H 0.996(5) 0.233(5) -0.549(5) 0.088(11) 1.0000 Uiso . . . . . .
H231 H 1.204(5) 0.014(5) -0.614(4) 0.077(9) 1.0000 Uiso . . . . . .
H241 H 1.434(4) -0.173(5) -0.430(4) 0.072(9) 1.0000 Uiso . . . . . .
H331 H 1.334(4) -0.404(4) -0.113(4) 0.069(9) 1.0000 Uiso . . . . . .
H332 H 1.219(3) -0.474(3) 0.038(3) 0.044(6) 1.0000 Uiso . . . . . .
H291 H 1.066(5) 0.164(4) -0.096(4) 0.069(9) 1.0000 Uiso . . . . . .
H341 H 1.1186 -0.4311 -0.1832 0.0883 1.0000 Uiso R . . . . .
H342 H 1.0856 -0.2289 -0.2302 0.0883 1.0000 Uiso R . . . . .
H343 H 0.9793 -0.3151 -0.0818 0.0883 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . S2 . C3 . 110.31(10) yes
C7 2_755 S20 . C21 . 101.22(10) yes
C25 . O29 . H291 . 107(2) no
C26 . O30 . C33 . 114.77(15) yes
S2 . C1 . C24 . 116.8(2) yes
S2 . C1 . C25 . 123.82(17) yes
C24 . C1 . C25 . 118.9(2) yes
S2 . C3 . C4 . 114.28(18) yes
S2 . C3 . C26 . 125.96(17) yes
C4 . C3 . C26 . 119.3(2) yes
C3 . C4 . C5 . 121.6(2) yes
C3 . C4 . H41 . 124(2) no
C5 . C4 . H41 . 114(2) no
C4 . C5 . C6 . 119.0(2) yes
C4 . C5 . H51 . 122(2) no
C6 . C5 . H51 . 119(2) no
C5 . C6 . C7 . 120.4(2) yes
C5 . C6 . H61 . 122(2) no
C7 . C6 . H61 . 118(2) no
S20 2_755 C7 . C6 . 119.26(19) yes
S20 2_755 C7 . C26 . 120.09(16) yes
C6 . C7 . C26 . 120.6(2) yes
S20 . C21 . C22 . 119.6(2) yes
S20 . C21 . C25 . 119.84(17) yes
C22 . C21 . C25 . 120.3(2) yes
C21 . C22 . C23 . 120.5(3) yes
C21 . C22 . H221 . 118(2) no
C23 . C22 . H221 . 121(2) no
C22 . C23 . C24 . 119.4(2) yes
C22 . C23 . H231 . 109.5(20) no
C24 . C23 . H231 . 131.0(20) no
C1 . C24 . C23 . 121.4(3) yes
C1 . C24 . H241 . 116(2) no
C23 . C24 . H241 . 123(2) no
C1 . C25 . C21 . 119.3(2) yes
C1 . C25 . O29 . 117.7(2) yes
C21 . C25 . O29 . 123.0(2) yes
C3 . C26 . O30 . 120.51(18) yes
C3 . C26 . C7 . 119.03(19) yes
O30 . C26 . C7 . 120.39(18) yes
O30 . C33 . C34 . 106.7(2) yes
O30 . C33 . H331 . 109.9(19) no
C34 . C33 . H331 . 109.5(20) no
O30 . C33 . H332 . 102.1(16) no
C34 . C33 . H332 . 110.1(16) no
H331 . C33 . H332 . 118(3) no
C33 . C34 . H341 . 109.6 no
C33 . C34 . H342 . 109.3 no
H341 . C34 . H342 . 109.5 no
C33 . C34 . H343 . 109.5 no
H341 . C34 . H343 . 109.5 no
H342 . C34 . H343 . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S2 . C1 . 1.769(2) yes
S2 . C3 . 1.766(2) yes
S20 . C7 2_755 1.780(2) yes
S20 . C21 . 1.776(2) yes
O29 . C25 . 1.359(2) yes
O29 . H291 . 0.82(4) no
O30 . C26 . 1.389(2) yes
O30 . C33 . 1.447(3) yes
C1 . C24 . 1.398(3) yes
C1 . C25 . 1.403(3) yes
C3 . C4 . 1.406(3) yes
C3 . C26 . 1.397(3) yes
C4 . C5 . 1.370(4) yes
C4 . H41 . 0.95(4) no
C5 . C6 . 1.385(4) yes
C5 . H51 . 0.92(3) no
C6 . C7 . 1.401(3) yes
C6 . H61 . 0.98(4) no
C7 . C26 . 1.386(3) yes
C21 . C22 . 1.394(3) yes
C21 . C25 . 1.397(3) yes
C22 . C23 . 1.374(5) yes
C22 . H221 . 0.93(4) no
C23 . C24 . 1.383(4) yes
C23 . H231 . 1.08(4) no
C24 . H241 . 0.95(4) no
C33 . C34 . 1.505(4) yes
C33 . H331 . 0.98(3) no
C33 . H332 . 0.93(3) no
C34 . H341 . 1.000 no
C34 . H342 . 1.000 no
C34 . H343 . 1.000 no
