#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/89/4508900.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_4508900
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            'C12 H18 O2 S'
_chemical_formula_weight         226.32
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 114.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.226(5)
_cell_length_b                   6.0154(12)
_cell_length_c                   9.885(2)
_cell_measurement_reflns_used    2990
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1252.5(5)
_computing_cell_refinement       'HKL Scalepack (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 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6149
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         5.25
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0527
_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)+(0.0780P)²+0.4712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                2929
_reflns_number_total             3537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060465msup1.cif
_cod_data_source_block           mms07_6b
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4508900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 0.76326(3) 0.79718(11) 0.21068(6) 0.04222(16) Uani 1 1 d U
O1 O 0.71578(9) 0.6189(4) 0.1257(2) 0.0561(5) Uani 1 1 d U
O2 O 0.85646(9) 1.1581(3) 0.1773(2) 0.0482(4) Uani 1 1 d U
H2 H 0.8357 1.1602 0.0843 0.058 Uiso 1 1 calc R
C1 C 0.82636(12) 0.7695(5) 0.1510(2) 0.0432(5) Uani 1 1 d U
H1B H 0.8444 0.6179 0.1752 0.052 Uiso 1 1 calc R
H1A H 0.8086 0.7878 0.0413 0.052 Uiso 1 1 calc R
C2 C 0.87914(12) 0.9387(5) 0.2241(3) 0.0426(5) Uani 1 1 d U
H2A H 0.8927 0.9303 0.3343 0.051 Uiso 1 1 calc R
C3 C 0.93696(16) 0.8794(5) 0.1934(4) 0.0591(7) Uani 1 1 d U
H3 H 0.9224 0.8687 0.0829 0.071 Uiso 1 1 calc R
C4 C 0.9863(2) 1.0563(9) 0.2501(7) 0.114(2) Uani 1 1 d U
H4A H 1.0036 1.0623 0.3591 0.137 Uiso 1 1 calc R
H4B H 0.9673 1.2001 0.2083 0.137 Uiso 1 1 calc R
H4C H 1.0206 1.0227 0.2201 0.137 Uiso 1 1 calc R
C5 C 0.9646(2) 0.6573(9) 0.2606(6) 0.0947(14) Uani 1 1 d U
H5A H 0.9982 0.6161 0.2299 0.114 Uiso 1 1 calc R
H5B H 0.9311 0.5441 0.2260 0.114 Uiso 1 1 calc R
H5C H 0.9824 0.6675 0.3697 0.114 Uiso 1 1 calc R
C11 C 0.80426(11) 0.6959(4) 0.3972(2) 0.0378(5) Uani 1 1 d U
C12 C 0.83189(12) 0.4873(4) 0.4265(3) 0.0411(5) Uani 1 1 d U
H12 H 0.8306 0.3941 0.3477 0.049 Uiso 1 1 calc R
C13 C 0.86149(11) 0.4174(4) 0.5736(3) 0.0441(5) Uani 1 1 d U
H13 H 0.8809 0.2749 0.5951 0.053 Uiso 1 1 calc R
C14 C 0.86356(12) 0.5509(5) 0.6905(3) 0.0447(5) Uani 1 1 d U
C15 C 0.83466(12) 0.7577(5) 0.6576(3) 0.0476(6) Uani 1 1 d U
H15 H 0.8353 0.8502 0.7360 0.057 Uiso 1 1 calc R
C16 C 0.80499(11) 0.8306(4) 0.5120(3) 0.0427(5) Uani 1 1 d U
H16 H 0.7851 0.9724 0.4904 0.051 Uiso 1 1 calc R
C7 C 0.89676(15) 0.4688(7) 0.8494(3) 0.0629(8) Uani 1 1 d U
H7A H 0.9380 0.5429 0.8988 0.076 Uiso 1 1 calc R
H7B H 0.9031 0.3078 0.8493 0.076 Uiso 1 1 calc R
H7C H 0.8707 0.5027 0.9030 0.076 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 0.0418(3) 0.0420(3) 0.0415(3) 0.0006(3) 0.0162(2) -0.0022(3)
O1 0.0512(10) 0.0599(12) 0.0469(10) 0.0008(9) 0.0107(8) -0.0123(9)
O2 0.0561(10) 0.0404(9) 0.0471(9) -0.0070(8) 0.0207(8) -0.0030(8)
C1 0.0558(13) 0.0423(14) 0.0364(9) -0.0034(10) 0.0242(9) -0.0042(11)
C2 0.0453(12) 0.0486(14) 0.0380(11) -0.0026(9) 0.0213(10) -0.0045(10)
C3 0.0575(16) 0.0591(17) 0.0725(19) -0.0021(14) 0.0389(15) 0.0002(13)
C4 0.076(3) 0.096(3) 0.194(6) -0.040(3) 0.080(3) -0.030(2)
C5 0.070(2) 0.089(3) 0.133(4) 0.023(3) 0.050(3) 0.028(2)
C11 0.0384(10) 0.0412(11) 0.0379(10) -0.0041(9) 0.0200(9) -0.0040(9)
C12 0.0470(13) 0.0392(12) 0.0426(11) -0.0067(9) 0.0242(10) 0.0001(9)
C13 0.0441(12) 0.0429(13) 0.0474(12) -0.0003(10) 0.0215(10) 0.0022(10)
C14 0.0388(12) 0.0583(15) 0.0384(11) -0.0033(10) 0.0178(10) -0.0049(10)
C15 0.0442(12) 0.0612(18) 0.0404(11) -0.0137(11) 0.0207(9) -0.0042(11)
C16 0.0406(11) 0.0427(15) 0.0476(11) -0.0089(10) 0.0215(9) -0.0007(9)
C7 0.0586(17) 0.086(2) 0.0443(13) 0.0027(15) 0.0215(13) 0.0009(15)
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
O1 S1 C11 106.14(11)
O1 S1 C1 104.78(12)
C11 S1 C1 98.77(11)
C2 C1 S1 112.69(16)
O2 C2 C1 110.6(2)
O2 C2 C3 112.7(2)
C1 C2 C3 110.3(2)
C4 C3 C5 110.4(4)
C4 C3 C2 111.0(3)
C5 C3 C2 111.3(3)
C12 C11 C16 120.9(2)
C12 C11 S1 121.59(17)
C16 C11 S1 117.48(19)
C11 C12 C13 118.4(2)
C12 C13 C14 121.7(2)
C15 C14 C13 118.6(2)
C15 C14 C7 121.5(3)
C13 C14 C7 119.9(3)
C16 C15 C14 120.7(2)
C15 C16 C11 119.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.514(2)
S1 C11 1.788(2)
S1 C1 1.804(2)
O2 C2 1.424(3)
C1 C2 1.522(3)
C2 C3 1.538(4)
C3 C4 1.490(5)
C3 C5 1.510(5)
C11 C12 1.383(3)
C11 C16 1.389(3)
C12 C13 1.386(3)
C13 C14 1.392(4)
C14 C15 1.385(4)
C14 C7 1.511(4)
C15 C16 1.379(4)
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 1.92 2.758(3) 171.1 4_655
C1 H1A O1 0.99 2.50 3.256(3) 133.4 4_655
C1 H1B O2 0.99 2.78 3.732(3) 161.7 1_545
C5 H5B O2 0.98 2.82 3.777(6) 166.7 1_545
C12 H12 O2 0.95 2.46 3.391(3) 165.6 1_545
C15 H15 O1 0.95 2.69 3.578(3) 155.2 4_656
C16 H16 C15 0.95 3.07 3.918(4) 150.1 4_656
C16 H16 C16 0.95 3.00 3.888(3) 156.7 4_656
C16 H16 C11 0.95 3.05 3.741(3) 130.9 4_656
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 179.38(17)
C11 S1 C1 C2 -71.25(19)
S1 C1 C2 O2 -65.7(2)
S1 C1 C2 C3 169.0(2)
O2 C2 C3 C4 49.8(4)
C1 C2 C3 C4 173.9(3)
O2 C2 C3 C5 173.2(3)
C1 C2 C3 C5 -62.7(4)
O1 S1 C11 C12 51.7(2)
C1 S1 C11 C12 -56.5(2)
O1 S1 C11 C16 -125.42(19)
C1 S1 C11 C16 126.31(19)
C16 C11 C12 C13 -1.3(3)
S1 C11 C12 C13 -178.36(18)
C11 C12 C13 C14 0.4(4)
C12 C13 C14 C15 0.6(4)
C12 C13 C14 C7 -179.6(2)
C13 C14 C15 C16 -0.6(4)
C7 C14 C15 C16 179.5(3)
C14 C15 C16 C11 -0.3(4)
C12 C11 C16 C15 1.2(3)
S1 C11 C16 C15 178.43(19)
O1 S1 C2 O2 120.51(16)
C11 S1 C2 O2 -128.07(14)
H2 O2 C2 H2A -164.2
H2 O2 S1 O1 22.0
H2 O2 C1 H1A 7.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71404565
