#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502238.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_1502238
loop_
_publ_author_name
'Gelat, Fabien'
'Jayashankaran, Jayadevan'
'Lohier, Jean-François'
'Gaumont, Annie-Claude'
'Perrio, Stéphane'
_publ_section_title
;
 Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid
 anions mediated by a Cinchona-derived phase-transfer reagent.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3170
_journal_page_last               3173
_journal_paper_doi               10.1021/ol2010962
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H13 Cl O3 S2'
_chemical_formula_sum            'C14 H13 Cl O3 S2'
_chemical_formula_weight         328.81
_chemical_name_systematic
; 
 2-[(4-Chlorophenyl)sulfinyl]ethyl Phenyl Sulfone 
;
_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                 112.1780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4437(2)
_cell_length_b                   5.73830(10)
_cell_length_c                   19.0506(3)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      3.05
_cell_volume                     1462.14(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30343
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0320
_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)+(0.0501P)²+0.3688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3312
_reflns_number_total             3918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2010962_si_001.cif
_cod_data_source_block           1i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1502238
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_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
S1 S 0.11993(3) 0.41279(6) 0.22004(2) 0.04363(11) Uani 1 1 d
S2 S 0.14927(2) 0.05683(6) 0.026255(18) 0.03636(10) Uani 1 1 d
C1 C 0.00479(10) 0.2629(2) 0.20442(7) 0.0393(3) Uani 1 1 d
C6 C 0.00676(13) 0.0530(3) 0.24048(9) 0.0487(3) Uani 1 1 d
C8 C 0.12630(10) 0.1140(2) 0.10952(8) 0.0349(3) Uani 1 1 d
C9 C 0.27550(10) 0.1337(3) 0.04746(8) 0.0385(3) Uani 1 1 d
C7 C 0.12398(12) 0.3704(3) 0.12679(8) 0.0414(3) Uani 1 1 d
C2 C -0.08528(12) 0.3630(3) 0.15933(9) 0.0490(3) Uani 1 1 d
C5 C -0.08176(14) -0.0591(3) 0.23053(10) 0.0538(4) Uani 1 1 d
C10 C 0.34966(12) -0.0257(3) 0.08528(10) 0.0510(4) Uani 1 1 d
C13 C 0.39815(15) 0.3970(4) 0.03855(12) 0.0635(5) Uani 1 1 d
C4 C -0.17069(12) 0.0402(3) 0.18482(9) 0.0515(4) Uani 1 1 d
C14 C 0.29881(13) 0.3475(3) 0.02480(10) 0.0516(4) Uani 1 1 d
C12 C 0.47162(13) 0.2372(4) 0.07494(12) 0.0639(5) Uani 1 1 d
C3 C -0.17370(12) 0.2498(4) 0.14955(10) 0.0561(4) Uani 1 1 d
C11 C 0.44814(14) 0.0288(4) 0.09898(12) 0.0638(5) Uani 1 1 d
Cl1 Cl -0.28211(4) -0.10457(12) 0.17132(4) 0.08540(19) Uani 1 1 d
O2 O 0.14072(8) -0.19134(19) 0.01438(6) 0.0501(3) Uani 1 1 d
O1 O 0.20039(8) 0.2638(2) 0.27359(6) 0.0534(3) Uani 1 1 d
O3 O 0.08795(8) 0.2078(2) -0.03340(6) 0.0498(3) Uani 1 1 d
H8 H 0.1756(13) 0.038(3) 0.1476(10) 0.048(5) Uiso 1 1 d
H6 H 0.1848(14) 0.451(3) 0.1293(10) 0.052(5) Uiso 1 1 d
H7 H 0.0645(13) 0.043(3) 0.0997(9) 0.043(4) Uiso 1 1 d
H5 H 0.0701(14) 0.452(3) 0.0919(11) 0.052(5) Uiso 1 1 d
H9 H 0.3332(15) -0.164(4) 0.1017(11) 0.065(6) Uiso 1 1 d
H4 H 0.0678(16) -0.008(4) 0.2699(12) 0.067(6) Uiso 1 1 d
H13 H 0.2488(15) 0.459(3) 0.0016(11) 0.062(5) Uiso 1 1 d
H12 H 0.4162(15) 0.547(4) 0.0260(11) 0.066(6) Uiso 1 1 d
H11 H 0.5396(17) 0.266(4) 0.0835(12) 0.080(7) Uiso 1 1 d
H10 H 0.493(2) -0.081(4) 0.1205(14) 0.090(8) Uiso 1 1 d
H1 H -0.0888(15) 0.505(4) 0.1345(11) 0.063(5) Uiso 1 1 d
H3 H -0.0833(16) -0.199(4) 0.2513(12) 0.072(6) Uiso 1 1 d
H2 H -0.2352(17) 0.318(4) 0.1214(13) 0.079(6) Uiso 1 1 d
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'
Cl Cl 0.1484 0.1585 '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 C1 105.82(7)
O1 S1 C7 106.73(7)
C1 S1 C7 98.26(6)
O3 S2 O2 118.76(7)
O3 S2 C9 107.74(7)
O2 S2 C9 107.62(7)
O3 S2 C8 109.20(7)
O2 S2 C8 106.86(7)
C9 S2 C8 105.96(6)
C6 C1 C2 120.55(15)
C6 C1 S1 119.45(11)
C2 C1 S1 119.93(12)
C5 C6 C1 119.63(15)
C5 C6 H4 122.1(13)
C1 C6 H4 118.2(13)
C7 C8 S2 113.75(10)
C7 C8 H8 111.5(11)
S2 C8 H8 105.7(11)
C7 C8 H7 111.6(10)
S2 C8 H7 103.3(10)
H8 C8 H7 110.6(15)
C14 C9 C10 121.08(14)
C14 C9 S2 120.09(11)
C10 C9 S2 118.81(12)
C8 C7 S1 110.79(10)
C8 C7 H6 112.2(11)
S1 C7 H6 104.4(11)
C8 C7 H5 114.4(11)
S1 C7 H5 107.7(11)
H6 C7 H5 106.8(16)
C3 C2 C1 119.55(15)
C3 C2 H1 118.1(12)
C1 C2 H1 122.3(12)
C4 C5 C6 119.34(16)
C4 C5 H3 118.5(14)
C6 C5 H3 122.1(14)
C11 C10 C9 119.16(17)
C11 C10 H9 120.8(13)
C9 C10 H9 120.0(12)
C12 C13 C14 120.34(18)
C12 C13 H12 119.7(12)
C14 C13 H12 119.8(12)
C3 C4 C5 121.57(16)
C3 C4 Cl1 119.33(13)
C5 C4 Cl1 119.10(14)
C9 C14 C13 118.59(16)
C9 C14 H13 120.9(12)
C13 C14 H13 120.5(12)
C11 C12 C13 120.64(16)
C11 C12 H11 117.9(14)
C13 C12 H11 121.4(14)
C4 C3 C2 119.34(15)
C4 C3 H2 119.8(14)
C2 C3 H2 120.7(14)
C12 C11 C10 120.15(18)
C12 C11 H10 123.1(16)
C10 C11 H10 116.6(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4923(12)
S1 C1 1.7946(15)
S1 C7 1.8157(15)
S2 O3 1.4376(11)
S2 O2 1.4399(11)
S2 C9 1.7680(14)
S2 C8 1.7695(14)
C1 C6 1.381(2)
C1 C2 1.384(2)
C6 C5 1.379(2)
C6 H4 0.92(2)
C8 C7 1.511(2)
C8 H8 0.913(18)
C8 H7 0.933(17)
C9 C14 1.384(2)
C9 C10 1.386(2)
C7 H6 0.977(19)
C7 H5 0.935(19)
C2 C3 1.381(2)
C2 H1 0.93(2)
C5 C4 1.374(2)
C5 H3 0.90(2)
C10 C11 1.382(2)
C10 H9 0.92(2)
C13 C12 1.375(3)
C13 C14 1.387(2)
C13 H12 0.96(2)
C4 C3 1.370(3)
C4 Cl1 1.7417(17)
C14 H13 0.94(2)
C12 C11 1.368(3)
C12 H11 0.95(2)
C3 H2 0.93(2)
C11 H10 0.89(3)
