#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:00:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178929 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/58/4115817.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_4115817
loop_
_publ_author_name
'Héctor Carrasco'
'Concepción Foces-Foces'
'Cirilo Pérez'
'Matías L. Rodríguez'
'Julio D. Martín'
_publ_contact_author
;                                                                               
      C.Foce-Foces
      Instituto de Quimica-Fisica Rocasolano-CSIC                               
      Departamento de Cristalografia                                            
      Serrano 119                                                               
      E-28006 Madrid                                                            
      Spain                                                                     
;
_publ_contact_author_email       cfoces@iqfr.csic.es
_publ_contact_author_fax         '+34 1 5642431'
_publ_contact_author_phone       '+34 1 5619400'
_publ_section_title
;
 Tubular Hydrogen-Bonded Networks Sustained by Water Molecules
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11970
_journal_page_last               11981
_journal_paper_doi               10.1021/ja011028t
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         'C13 H20 O6 S'
_chemical_formula_sum            'C13 H20 O6 S'
_chemical_formula_weight         304.35
_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                97.0060(10)
_cell_angle_beta                 96.6130(10)
_cell_angle_gamma                94.8825(20)
_cell_formula_units_Z            2
_cell_length_a                   7.47390(10)
_cell_length_b                   9.17830(10)
_cell_length_c                   9.98890(10)
_cell_measurement_temperature    298(2)
_cell_volume                     672.149(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0318
_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       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7659
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0.08
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.8791
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       Plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.2951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                2634
_reflns_number_total             3203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja011028t_12.cif
_cod_data_source_block           1m
_cod_original_cell_volume        672.149(13)
_cod_database_code               4115817
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 0.34549(06) 0.20252(04) -0.12692(04) .0295(1) Uani 1 1 d .
O3 O 0.21174(19) 0.63082(13) 0.17452(13) .0377(3) Uani 1 1 d .
O4 O 0.26690(20) 0.65040(13) 0.40014(13) .0475(4) Uani 1 1 d .
H4A H 0.27780 0.73880 0.39370 .071 Uiso 1 1 calc R
O1 O 0.21886(15) 0.16601(11) 0.21154(11) .0237(2) Uani 1 1 d .
O2 O 0.29316(18) -0.06634(12) 0.35376(13) .0354(3) Uani 1 1 d .
H2A H 0.37030 -0.08780 0.30471 .053 Uiso 1 1 calc R
O5 O 0.34470(20) 0.33310(15) -0.19288(14) .0435(3) Uani 1 1 d .
O6 O 0.39680(20) 0.07058(15) -0.20183(14) .0453(4) Uani 1 1 d .
C5 C 0.17040(20) 0.41182(16) 0.28298(15) .0230(3) Uani 1 1 d .
C6 C 0.26720(20) 0.34765(16) 0.40322(16) .0251(3) Uani 1 1 d .
H6B H 0.22400 0.38189 0.48830 .030 Uiso 1 1 calc R
H6A H 0.39750 0.37000 0.41170 .030 Uiso 1 1 calc R
C1 C 0.20940(20) 0.18374(16) 0.35736(15) .0236(3) Uani 1 1 d .
C2 C 0.01370(20) 0.14920(18) 0.38256(18) .0298(4) Uani 1 1 d .
H2B H -0.02180 0.04429 0.35820 .036 Uiso 1 1 calc R
H2C H 0.00420 0.17440 0.47850 .036 Uiso 1 1 calc R
C3 C -0.11370(20) 0.23538(19) 0.29930(19) .0317(4) Uani 1 1 d .
H3A H -0.13990 0.18450 0.20720 .038 Uiso 1 1 calc R
H3B H -0.22690 0.23690 0.33790 .038 Uiso 1 1 calc R
C4 C -0.03620(20) 0.39489(18) 0.29439(18) .0292(3) Uani 1 1 d .
H4C H -0.10020 0.43120 0.21710 .035 Uiso 1 1 calc R
H4B H -0.05820 0.45600 0.37600 .035 Uiso 1 1 calc R
C7 C 0.22070(20) 0.57453(17) 0.27772(17) .0270(3) Uani 1 1 d .
C9 C 0.22240(20) 0.30792(16) 0.16160(15) .0213(3) Uani 1 1 d .
C10 C 0.41540(20) 0.35264(17) 0.13050(17) .0268(3) Uani 1 1 d .
H10A H 0.49720 0.36840 0.21490 .032 Uiso 1 1 calc R
H10B H 0.41640 0.44539 0.09310 .032 Uiso 1 1 calc R
C11 C 0.48480(20) 0.23792(19) 0.03102(17) .0297(4) Uani 1 1 d .
H11A H 0.60640 0.27240 0.01630 .036 Uiso 1 1 calc R
H11B H 0.49090 0.14679 0.07051 .036 Uiso 1 1 calc R
C12 C 0.12980(20) 0.16632(19) -0.07523(17) .0302(4) Uani 1 1 d .
H12A H 0.12440 0.07450 -0.03630 .036 Uiso 1 1 calc R
H12B H 0.03790 0.15560 -0.15360 .036 Uiso 1 1 calc R
C13 C 0.09180(20) 0.29168(18) 0.02993(16) .0268(3) Uani 1 1 d .
H13A H -0.03100 0.27360 0.05070 .032 Uiso 1 1 calc R
H13B H 0.10090 0.38350 -0.00879 .032 Uiso 1 1 calc R
C8 C 0.33600(20) 0.08226(17) 0.41847(17) .0295(4) Uani 1 1 d .
H8A H 0.32660 0.08600 0.51490 .035 Uiso 1 1 calc R
H8B H 0.45970 0.11570 0.40840 .035 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'
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
O5 S1 O6 117.47(9)
O5 S1 C11 110.46(8)
O5 S1 C12 108.12(9)
O6 S1 C11 108.12(8)
O6 S1 C12 109.97(8)
C11 S1 C12 101.53(8)
C9 O1 C1 110.49(10)
C7 C5 C6 115.80(11)
C7 C5 C9 114.09(13)
C7 C5 C4 106.05(12)
C6 C5 C9 100.50(12)
C6 C5 C4 107.56(13)
C9 C5 C4 112.85(11)
C1 C6 C5 99.31(11)
O1 C1 C8 107.19(12)
O1 C1 C2 109.33(11)
O1 C1 C6 104.03(12)
C8 C1 C2 112.88(13)
C8 C1 C6 113.98(12)
C2 C1 C6 108.98(13)
C1 C2 C3 111.04(14)
C2 C3 C4 113.37(12)
C3 C4 C5 113.78(13)
O3 C7 O4 123.20(15)
O3 C7 C5 124.18(14)
O4 C7 C5 112.54(14)
O1 C9 C13 108.21(11)
O1 C9 C10 108.92(12)
O1 C9 C5 103.00(12)
C13 C9 C10 108.92(13)
C13 C9 C5 115.69(13)
C10 C9 C5 111.75(11)
C11 C10 C9 113.29(12)
C10 C11 S1 112.37(11)
C13 C12 S1 110.60(10)
C9 C13 C12 112.79(13)
O2 C8 C1 111.08(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.4365(15)
S1 O6 1.4483(14)
S1 C11 1.7657(16)
S1 C12 1.7658(16)
O3 C7 1.206(2)
O4 C7 1.324(2)
O1 C9 1.4497(19)
O1 C1 1.4564(19)
O2 C8 1.4295(18)
C5 C7 1.517(2)
C5 C6 1.536(2)
C5 C9 1.556(2)
C5 C4 1.557(2)
C6 C1 1.528(2)
C1 C8 1.514(2)
C1 C2 1.526(2)
C2 C3 1.527(2)
C3 C4 1.537(2)
C9 C13 1.529(2)
C9 C10 1.542(2)
C10 C11 1.524(2)
C12 C13 1.529(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O6 0.82 2.13 2.913(2) 161 2_655
O4 H4A O2 0.82 1.88 2.691(1) 172 1_565
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
O5 S1 C11 C10 63.18(14)
O6 S1 C11 C10 -167.02(12)
C12 S1 C11 C10 -51.33(14)
O5 S1 C12 C13 -63.35(13)
O6 S1 C12 C13 167.21(12)
C11 S1 C12 C13 52.89(13)
C9 O1 C1 C6 -17.40(15)
C9 O1 C1 C2 98.89(13)
C9 O1 C1 C8 -138.45(12)
C1 O1 C9 C5 -12.38(14)
C1 O1 C9 C10 106.38(13)
C1 O1 C9 C13 -135.35(12)
C4 C5 C6 C1 71.84(14)
C7 C5 C6 C1 -169.80(13)
C9 C5 C6 C1 -46.38(13)
C6 C5 C4 C3 -56.23(17)
C7 C5 C4 C3 179.30(14)
C9 C5 C4 C3 53.70(19)
C6 C5 C7 O3 152.92(16)
C6 C5 C7 O4 -30.4(2)
C4 C5 C7 O3 -87.88(19)
C4 C5 C7 O4 88.78(15)
C9 C5 C7 O3 37.0(2)
C9 C5 C7 O4 -146.39(14)
C6 C5 C9 O1 36.88(13)
C6 C5 C9 C10 -79.89(14)
C6 C5 C9 C13 154.71(13)
C4 C5 C9 O1 -77.40(15)
C4 C5 C9 C10 165.84(13)
C4 C5 C9 C13 40.44(18)
C7 C5 C9 O1 161.47(11)
C7 C5 C9 C10 44.70(17)
C7 C5 C9 C13 -80.70(16)
C5 C6 C1 O1 39.76(14)
C5 C6 C1 C2 -76.77(15)
C5 C6 C1 C8 156.16(13)
O1 C1 C2 C3 -50.98(16)
C6 C1 C2 C3 62.12(16)
C8 C1 C2 C3 -170.19(13)
O1 C1 C8 O2 -55.08(16)
C6 C1 C8 O2 -169.62(13)
C2 C1 C8 O2 65.36(17)
C1 C2 C3 C4 -40.3(2)
C2 C3 C4 C5 38.5(2)
O1 C9 C10 C11 55.98(16)
C5 C9 C10 C11 169.11(13)
C13 C9 C10 C11 -61.84(17)
O1 C9 C13 C12 -53.75(17)
C5 C9 C13 C12 -168.64(13)
C10 C9 C13 C12 64.52(17)
C9 C10 C11 S1 59.12(17)
S1 C12 C13 C9 -63.66(16)
