#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:19:21 +0100 (jue 24 de mar de 2016) $
#$Revision: 179624 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/88/4508898.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_4508898
loop_
_publ_author_name
'Asensio, Gregorio'
'Medio-Simon, Mercedes'
'Alemán, Pedro'
'de Arellano, Carmen Ramírez'
_publ_section_title
;
 The Role of Organic Fluorine in the Supramolecular Assembly of
 Halogenated β-Hydroxysulphoxides Diastereomers
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2769
_journal_paper_doi               10.1021/cg060465m
_journal_volume                  6
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H11 F3 O2 S'
_chemical_formula_weight         252.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.41(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1239(12)
_cell_length_b                   9.3422(19)
_cell_length_c                   10.132(2)
_cell_measurement_reflns_used    3149
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     566.1(2)
_computing_cell_refinement       'HKL Denzo (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXTL v6.14 (Bruker AXS, 2000-2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  Nonius-KappaCCD
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6231
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         5.23
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0418
_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)+(0.0655P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                2462
_reflns_number_total             3252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060465msup1.cif
_cod_data_source_block           mms04_3bI
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4508898
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.50320(8) -0.04316(6) 0.99076(4) 0.04918(15) Uani 1 1 d U
O1 O 0.2600(2) -0.0458(3) 0.99551(15) 0.0686(4) Uani 1 1 d U
O2 O 0.9724(2) -0.05086(19) 1.15552(17) 0.0608(4) Uani 1 1 d U
H2 H 1.0683 -0.0557 1.1075 0.091 Uiso 1 1 calc R
F1 F 0.8939(3) 0.29900(16) 1.27500(15) 0.0801(5) Uani 1 1 d U
F2 F 0.9490(3) 0.10103(17) 1.38519(13) 0.0765(4) Uani 1 1 d U
F3 F 1.2010(3) 0.1826(2) 1.28463(19) 0.0900(6) Uani 1 1 d U
C1 C 0.6275(3) 0.0728(2) 1.1307(2) 0.0466(4) Uani 1 1 d U
H1B H 0.5590 0.1690 1.1158 0.056 Uiso 1 1 calc R
H1A H 0.5954 0.0339 1.2154 0.056 Uiso 1 1 calc R
C2 C 0.8791(3) 0.0858(2) 1.1455(2) 0.0489(4) Uani 1 1 d U
H2A H 0.9127 0.1363 1.0651 0.059 Uiso 1 1 calc R
C3 C 0.9809(4) 0.1678(3) 1.2735(2) 0.0614(6) Uani 1 1 d U
C11 C 0.5266(3) 0.07131(19) 0.85293(18) 0.0414(4) Uani 1 1 d U
C12 C 0.7155(3) 0.0635(2) 0.7989(2) 0.0486(4) Uani 1 1 d U
H12 H 0.8322 -0.0018 0.8348 0.058 Uiso 1 1 calc R
C13 C 0.7319(4) 0.1518(3) 0.6921(2) 0.0532(5) Uani 1 1 d U
H13 H 0.8626 0.1483 0.6558 0.064 Uiso 1 1 calc R
C14 C 0.5600(4) 0.2463(2) 0.6366(2) 0.0526(5) Uani 1 1 d U
C15 C 0.3691(4) 0.2473(2) 0.6897(2) 0.0518(5) Uani 1 1 d U
H15 H 0.2482 0.3081 0.6506 0.062 Uiso 1 1 calc R
C16 C 0.3509(3) 0.1620(2) 0.7985(2) 0.0470(4) Uani 1 1 d U
H16 H 0.2206 0.1654 0.8351 0.056 Uiso 1 1 calc R
C7 C 0.5843(5) 0.3452(3) 0.5226(3) 0.0752(7) Uani 1 1 d U
H7A H 0.7226 0.4006 0.5493 0.113 Uiso 1 1 calc R
H7B H 0.4563 0.4106 0.5026 0.113 Uiso 1 1 calc R
H7C H 0.5897 0.2886 0.4420 0.113 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0503(3) 0.0418(2) 0.0548(3) -0.0010(2) 0.00988(18) -0.0054(2)
O1 0.0509(8) 0.0930(11) 0.0637(8) 0.0018(11) 0.0164(6) -0.0214(10)
O2 0.0493(7) 0.0512(8) 0.0871(10) 0.0029(9) 0.0259(7) -0.0001(8)
F1 0.1127(13) 0.0529(8) 0.0707(9) -0.0103(6) 0.0111(8) -0.0150(8)
F2 0.0890(11) 0.0858(11) 0.0508(7) 0.0078(7) 0.0067(6) -0.0069(8)
F3 0.0671(10) 0.1103(15) 0.0845(10) -0.0121(9) -0.0016(8) -0.0321(9)
C1 0.0490(10) 0.0458(10) 0.0457(9) 0.0017(8) 0.0115(8) 0.0005(9)
C2 0.0502(11) 0.0438(10) 0.0531(10) 0.0035(8) 0.0118(8) -0.0024(9)
C3 0.0650(14) 0.0628(14) 0.0535(12) 0.0031(10) 0.0063(10) -0.0121(10)
C11 0.0416(10) 0.0370(8) 0.0443(9) -0.0039(7) 0.0062(7) -0.0025(8)
C12 0.0403(10) 0.0515(10) 0.0524(10) -0.0072(8) 0.0067(8) 0.0052(8)
C13 0.0434(10) 0.0664(12) 0.0501(10) -0.0079(9) 0.0108(8) -0.0028(9)
C14 0.0573(12) 0.0547(11) 0.0425(9) -0.0083(8) 0.0037(8) -0.0099(9)
C15 0.0498(11) 0.0454(10) 0.0539(11) -0.0063(8) -0.0028(8) 0.0057(8)
C16 0.0395(9) 0.0474(10) 0.0528(10) -0.0079(8) 0.0069(8) 0.0041(8)
C7 0.0842(18) 0.0775(18) 0.0582(14) 0.0099(12) 0.0021(12) -0.0169(14)
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'
F F 0.0171 0.0103 '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
O1 S1 C11 106.34(10)
O1 S1 C1 103.74(10)
C11 S1 C1 99.34(9)
C2 C1 S1 111.77(14)
O2 C2 C3 108.22(18)
O2 C2 C1 108.94(16)
C3 C2 C1 110.23(18)
F3 C3 F1 107.5(2)
F3 C3 F2 107.70(19)
F1 C3 F2 106.6(2)
F3 C3 C2 110.3(2)
F1 C3 C2 112.34(19)
F2 C3 C2 112.22(19)
C12 C11 C16 121.21(19)
C12 C11 S1 119.39(15)
C16 C11 S1 119.34(15)
C13 C12 C11 119.06(19)
C12 C13 C14 121.16(19)
C15 C14 C13 118.24(19)
C15 C14 C7 121.4(2)
C13 C14 C7 120.3(2)
C16 C15 C14 121.57(19)
C15 C16 C11 118.68(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.5007(16)
S1 C11 1.7889(19)
S1 C1 1.816(2)
O2 C2 1.394(3)
F1 C3 1.338(3)
F2 C3 1.343(3)
F3 C3 1.335(3)
C1 C2 1.520(3)
C2 C3 1.520(3)
C11 C12 1.384(3)
C11 C16 1.387(3)
C12 C13 1.382(3)
C13 C14 1.396(3)
C14 C15 1.388(3)
C14 C7 1.511(3)
C15 C16 1.384(3)
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 H2 O1 0.84 1.80 2.638(2) 173.0 1_655
C12 H12 O1 0.95 2.80 3.643(3) 148.1 1_655
C12 H12 F1 0.95 2.88 3.627(3) 135.9 2_747
C7 H7A F2 0.98 2.72 3.688(3) 168.4 2_757
C7 H7C F1 0.98 2.77 3.481(4) 129.6 1_554
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
O1 S1 C1 C2 178.32(14)
C11 S1 C1 C2 -72.18(15)
S1 C1 C2 O2 -54.24(19)
S1 C1 C2 C3 -172.85(14)
O2 C2 C3 F3 62.6(2)
C1 C2 C3 F3 -178.32(18)
O2 C2 C3 F1 -177.49(18)
C1 C2 C3 F1 -58.4(2)
O2 C2 C3 F2 -57.4(3)
C1 C2 C3 F2 61.6(3)
O1 S1 C11 C12 -161.63(15)
C1 S1 C11 C12 90.97(16)
O1 S1 C11 C16 15.67(17)
C1 S1 C11 C16 -91.73(16)
C16 C11 C12 C13 2.5(3)
S1 C11 C12 C13 179.74(15)
C11 C12 C13 C14 -1.3(3)
C12 C13 C14 C15 -1.2(3)
C12 C13 C14 C7 178.1(2)
C13 C14 C15 C16 2.6(3)
C7 C14 C15 C16 -176.7(2)
C14 C15 C16 C11 -1.4(3)
C12 C11 C16 C15 -1.2(3)
S1 C11 C16 C15 -178.43(14)
O1 S1 C2 O2 127.37(15)
C11 S1 C2 O2 -120.33(12)
H2 O2 C2 H2A 16.5
H2 O2 S1 O1 173.6
H2 O2 C1 H1A 178.5
