#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206729.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_2206729
loop_
_publ_author_name
'Gaël Labat'
'Joan Halfpenny'
_publ_section_title
;
1,5-Bis(3-thienyloxy)-3-oxapentane: a thiophene-based precursor for
thiophene-based azacryptand Mannich bases
;
_journal_coeditor_code           IS6111
_journal_issue                   9
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o2813
_journal_page_last               o22814
_journal_paper_doi               10.1107/S1600536805024517
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H14 O3 S2'
_chemical_formula_moiety         'C12 H14 O3 S2'
_chemical_formula_sum            'C12 H14 O3 S2'
_chemical_formula_weight         270.35
_chemical_name_systematic
;
1,5-Bis(2-thienyloxy)-3-oxapentane
;
_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'
_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                 100.960(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2998(4)
_cell_length_b                   19.4005(18)
_cell_length_c                   12.7277(9)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.65
_cell_volume                     1284.78(18)
_computing_cell_refinement       'CELL (Stoe & Cie, 2002)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 2002)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       ω
_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  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10146
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0331
_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)+(0.0331P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                1609
_reflns_number_total             2509
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6111.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206729
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_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.16435(11) 0.52004(3) 0.70026(4) 0.03420(16) Uani d . 1 S
S2 0.63304(12) 0.70048(3) 1.53098(5) 0.03781(17) Uani d . 1 S
O1 -0.2011(3) 0.62079(7) 0.88858(11) 0.0283(3) Uani d . 1 O
O2 -0.2260(3) 0.63598(7) 1.10645(10) 0.0294(4) Uani d . 1 O
O3 0.0678(3) 0.63305(7) 1.31584(11) 0.0278(3) Uani d . 1 O
C1 -0.0383(4) 0.52702(11) 0.79012(15) 0.0257(5) Uani d . 1 C
H1A -0.1231 0.4894 0.8162 0.031 Uiso calc R 1 H
C2 -0.0605(4) 0.59373(10) 0.81876(15) 0.0240(4) Uani d . 1 C
C3 0.0848(4) 0.63996(11) 0.76818(16) 0.0298(5) Uani d . 1 C
H3A 0.0888 0.6884 0.7790 0.036 Uiso calc R 1 H
C4 0.2175(4) 0.60675(12) 0.70255(17) 0.0353(6) Uani d . 1 C
H4A 0.3274 0.6291 0.6624 0.042 Uiso calc R 1 H
C5 -0.3283(4) 0.57264(10) 0.94515(16) 0.0267(5) Uani d . 1 C
H5B -0.2057 0.5371 0.9793 0.032 Uiso calc R 1 H
H5A -0.4691 0.5495 0.8954 0.032 Uiso calc R 1 H
C6 -0.4344(4) 0.61194(11) 1.02881(16) 0.0303(5) Uani d . 1 C
H6A -0.5387 0.6513 0.9955 0.036 Uiso calc R 1 H
H6B -0.5459 0.5816 1.0628 0.036 Uiso calc R 1 H
C7 -0.3098(5) 0.66629(12) 1.19548(16) 0.0370(6) Uani d . 1 C
H7A -0.4051 0.6318 1.2301 0.044 Uiso calc R 1 H
H7B -0.4268 0.7053 1.1711 0.044 Uiso calc R 1 H
C8 -0.0825(5) 0.69130(11) 1.27361(16) 0.0335(5) Uani d . 1 C
H8A 0.0214 0.7227 1.2377 0.040 Uiso calc R 1 H
H8B -0.1395 0.7169 1.3322 0.040 Uiso calc R 1 H
C9 0.3544(4) 0.70933(11) 1.43801(16) 0.0309(5) Uani d . 1 C
H9A 0.2668 0.7517 1.4202 0.037 Uiso calc R 1 H
C10 0.2762(4) 0.64727(10) 1.39336(15) 0.0242(5) Uani d . 1 C
C11 0.4412(4) 0.59251(11) 1.43531(16) 0.0295(5) Uani d . 1 C
H11A 0.4134 0.5458 1.4138 0.035 Uiso calc R 1 H
C12 0.6421(5) 0.61409(12) 1.50917(17) 0.0351(5) Uani d . 1 C
H12A 0.7737 0.5845 1.5450 0.042 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'
O O 0.0106 0.0060 '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
C4 S1 C1 91.89(10) y
C12 S2 C9 91.92(11) y
C2 O1 C5 116.42(15) y
C6 O2 C7 111.88(16) y
C10 O3 C8 115.46(16) y
C2 C1 S1 110.59(15) y
C2 C1 H1A 124.7 ?
S1 C1 H1A 124.7 ?
C1 C2 O1 128.80(18) y
C1 C2 C3 113.61(18) y
O1 C2 C3 117.59(17) y
C4 C3 C2 111.76(19) y
C4 C3 H3A 124.1 ?
C2 C3 H3A 124.1 ?
C3 C4 S1 112.15(16) y
C3 C4 H4A 123.9 ?
S1 C4 H4A 123.9 ?
O1 C5 C6 107.58(16) y
O1 C5 H5B 110.2 ?
C6 C5 H5B 110.2 ?
O1 C5 H5A 110.2 ?
C6 C5 H5A 110.2 ?
H5B C5 H5A 108.5 ?
O2 C6 C5 108.33(17) y
O2 C6 H6A 110.0 ?
C5 C6 H6A 110.0 ?
O2 C6 H6B 110.0 ?
C5 C6 H6B 110.0 ?
H6A C6 H6B 108.4 ?
O2 C7 C8 109.35(18) y
O2 C7 H7A 109.8 ?
C8 C7 H7A 109.8 ?
O2 C7 H7B 109.8 ?
C8 C7 H7B 109.8 ?
H7A C7 H7B 108.3 ?
O3 C8 C7 108.41(18) ?
O3 C8 H8A 110.0 ?
C7 C8 H8A 110.0 ?
O3 C8 H8B 110.0 ?
C7 C8 H8B 110.0 ?
H8A C8 H8B 108.4 ?
C10 C9 S2 110.66(17) y
C10 C9 H9A 124.7 ?
S2 C9 H9A 124.7 ?
C9 C10 O3 128.5(2) y
C9 C10 C11 112.9(2) y
O3 C10 C11 118.64(18) y
C12 C11 C10 112.3(2) y
C12 C11 H11A 123.8 ?
C10 C11 H11A 123.8 ?
C11 C12 S2 112.15(18) y
C11 C12 H12A 123.9 ?
S2 C12 H12A 123.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 1.705(2) y
S1 C1 1.717(2) y
S2 C12 1.701(2) y
S2 C9 1.716(3) y
O1 C2 1.368(2) y
O1 C5 1.425(2) y
O2 C6 1.414(3) y
O2 C7 1.421(2) y
O3 C10 1.362(3) y
O3 C8 1.428(2) y
C1 C2 1.356(3) y
C1 H1A 0.9500 ?
C2 C3 1.414(3) ?
C3 C4 1.353(3) y
C3 H3A 0.9500 ?
C4 H4A 0.9500 ?
C5 C6 1.503(3) y
C5 H5B 0.9900 ?
C5 H5A 0.9900 ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C8 1.490(3) y
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.362(3) y
C9 H9A 0.9500 ?
C10 C11 1.414(3) y
C11 C12 1.346(3) y
C11 H11A 0.9500 ?
C12 H12A 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9A O1 4_676 0.95 2.52 3.358(2) 148
C12 H12A S1 1_656 0.95 2.86 3.787(2) 164
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
C4 S1 C1 C2 0.16(17)
S1 C1 C2 O1 -179.53(17)
S1 C1 C2 C3 0.3(2)
C5 O1 C2 C1 4.9(3)
C5 O1 C2 C3 -174.89(18)
C1 C2 C3 C4 -0.7(3)
O1 C2 C3 C4 179.13(19)
C2 C3 C4 S1 0.8(2)
C1 S1 C4 C3 -0.55(18)
C2 O1 C5 C6 171.17(17)
C7 O2 C6 C5 -172.63(17)
O1 C5 C6 O2 -67.9(2)
C6 O2 C7 C8 -179.31(17)
C10 O3 C8 C7 -176.48(16)
O2 C7 C8 O3 -65.7(2)
C12 S2 C9 C10 0.02(15)
S2 C9 C10 O3 -178.87(15)
S2 C9 C10 C11 0.5(2)
C8 O3 C10 C9 2.4(3)
C8 O3 C10 C11 -176.98(16)
C9 C10 C11 C12 -1.0(2)
O3 C10 C11 C12 178.47(17)
C10 C11 C12 S2 1.0(2)
C9 S2 C12 C11 -0.60(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9283556
