##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1416521'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-Methoxy-2-[(4-methoxyphenyl)sulfanyl]-1-phenylethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 O3 S'
_chemical_formula_sum     'C16 H16 O3 S'
_chemical_formula_iupac     'C16 H16 O3 S'
_chemical_formula_weight     288.35
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P c a 21'
_space_group_name_Hall     'P 2c -2ac'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y, z+1/2'
    'x+1/2, -y, z'
_cell_length_a     18.769(3)
_cell_length_b     7.6430(10)
_cell_length_c     10.0578(16)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1442.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2745
_cell_measurement_theta_min     2.17
_cell_measurement_theta_max     25.09
_cell_measurement_temperature     296(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.373
_exptl_crystal_size_mid     0.161
_exptl_crystal_size_min     0.092
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.228
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_shelx_estimated_absorpt_T_min     0.920
_shelx_estimated_absorpt_T_max     0.979
_exptl_absorpt_correction_T_min     0.6181
_exptl_absorpt_correction_T_max     0.7452
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6725
_diffrn_reflns_av_R_equivalents     0.0258
_diffrn_reflns_theta_min     2.170
_diffrn_reflns_theta_max     25.406
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_limit_l_max     12
_refine_special_details     ?
_reflns_number_total     1935
_reflns_number_gt     1627
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0426
_refine_ls_R_factor_gt     0.0314
_refine_ls_wR_factor_gt     0.0701
_refine_ls_wR_factor_ref     0.0759
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     1935
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0337P)²+0.2623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.121
_refine_diff_density_min     -0.141
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 418 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     0.09(4)
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'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SIR (Burla et al.,  2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and  DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
Marvinsketch (ChemAxon, 2010) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.56536(5) 0.23724(10) 0.74255(12) 0.0585(3) Uani d 1 . .
    O O1 0.53351(13) 0.6345(3) 0.9109(3) 0.0608(6) Uani d 1 . .
    O O2 0.44516(10) 0.4243(3) 0.7959(3) 0.0588(6) Uani d 1 . .
    O O3 0.67048(13) 0.2149(3) 1.2961(3) 0.0702(8) Uani d 1 . .
    C C1 0.7294(2) 0.8300(5) 0.6168(5) 0.0670(11) Uani d 1 . .
    H H1 0.7687 0.8842 0.5784 0.080 Uiso calc 1 . .
    C C2 0.70618(18) 0.8808(4) 0.7391(5) 0.0707(11) Uani d 1 . .
    H H2 0.7294 0.9710 0.7834 0.085 Uiso calc 1 . .
    C C3 0.64887(17) 0.8002(4) 0.7975(4) 0.0566(9) Uani d 1 . .
    H H3 0.6338 0.8355 0.8814 0.068 Uiso calc 1 . .
    C C4 0.61332(15) 0.6666(4) 0.7325(4) 0.0441(7) Uani d 1 . .
    C C5 0.63593(19) 0.6186(5) 0.6074(4) 0.0587(9) Uani d 1 . .
    H H5 0.6117 0.5320 0.5608 0.070 Uiso calc 1 . .
    C C6 0.6949(2) 0.6995(5) 0.5506(4) 0.0696(11) Uani d 1 . .
    H H6 0.7108 0.6644 0.4672 0.083 Uiso calc 1 . .
    C C7 0.55159(15) 0.5857(4) 0.8007(3) 0.0439(7) Uani d 1 . .
    C C8 0.51146(15) 0.4382(3) 0.7343(4) 0.0455(7) Uani d 1 . .
    H H8 0.5041 0.4685 0.6407 0.055 Uiso calc 1 . .
    C C9 0.3949(2) 0.3296(5) 0.7185(4) 0.0718(12) Uani d 1 . .
    H H9A 0.4129 0.2143 0.7012 0.108 Uiso calc 1 . .
    H H9B 0.3871 0.3894 0.6358 0.108 Uiso calc 1 . .
    H H9C 0.3507 0.3213 0.7663 0.108 Uiso calc 1 . .
    C C10 0.59396(18) 0.2334(4) 0.9103(4) 0.0448(8) Uani d 1 . .
    C C11 0.55035(17) 0.1718(4) 1.0103(4) 0.0474(8) Uani d 1 . .
    H H11 0.5045 0.1348 0.9897 0.057 Uiso calc 1 . .
    C C12 0.57361(17) 0.1641(4) 1.1405(4) 0.0493(9) Uani d 1 . .
    H H12 0.5434 0.1230 1.2068 0.059 Uiso calc 1 . .
    C C13 0.64116(18) 0.2170(4) 1.1714(4) 0.0491(9) Uani d 1 . .
    C C14 0.68553(18) 0.2783(4) 1.0714(4) 0.0610(10) Uani d 1 . .
    H H14 0.7316 0.3143 1.0919 0.073 Uiso calc 1 . .
    C C15 0.66189(18) 0.2860(4) 0.9429(4) 0.0550(9) Uani d 1 . .
    H H15 0.6921 0.3273 0.8767 0.066 Uiso calc 1 . .
    C C16 0.6275(2) 0.1561(6) 1.4024(4) 0.0749(11) Uani d 1 . .
    H H16A 0.6538 0.1639 1.4841 0.112 Uiso calc 1 . .
    H H16B 0.6138 0.0367 1.3871 0.112 Uiso calc 1 . .
    H H16C 0.5856 0.2277 1.4083 0.112 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C10 . 1.771(4) ?
    S1 C8 . 1.841(3) ?
    O1 C7 . 1.217(4) ?
    O2 C8 . 1.394(3) ?
    O2 C9 . 1.421(4) ?
    O3 C13 . 1.370(4) ?
    O3 C16 . 1.413(5) ?
    C1 C2 . 1.361(6) ?
    C1 C6 . 1.363(6) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.372(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.384(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.377(5) ?
    C4 C7 . 1.482(4) ?
    C5 C6 . 1.390(5) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.511(4) ?
    C8 H8 . 0.9800 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 C15 . 1.376(5) ?
    C10 C11 . 1.380(5) ?
    C11 C12 . 1.381(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.367(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.387(5) ?
    C14 C15 . 1.368(6) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 S1 C8 . . 102.90(15) ?
    C8 O2 C9 . . 112.8(3) ?
    C13 O3 C16 . . 117.8(3) ?
    C2 C1 C6 . . 119.8(4) ?
    C2 C1 H1 . . 120.1 ?
    C6 C1 H1 . . 120.1 ?
    C1 C2 C3 . . 120.7(4) ?
    C1 C2 H2 . . 119.7 ?
    C3 C2 H2 . . 119.7 ?
    C2 C3 C4 . . 120.4(4) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 118.6(3) ?
    C5 C4 C7 . . 123.6(3) ?
    C3 C4 C7 . . 117.8(3) ?
    C4 C5 C6 . . 120.2(4) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C1 C6 C5 . . 120.2(4) ?
    C1 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    O1 C7 C4 . . 120.8(3) ?
    O1 C7 C8 . . 119.4(3) ?
    C4 C7 C8 . . 119.8(3) ?
    O2 C8 C7 . . 107.8(2) ?
    O2 C8 S1 . . 114.0(2) ?
    C7 C8 S1 . . 109.2(2) ?
    O2 C8 H8 . . 108.6 ?
    C7 C8 H8 . . 108.6 ?
    S1 C8 H8 . . 108.6 ?
    O2 C9 H9A . . 109.5 ?
    O2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    O2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C15 C10 C11 . . 118.4(3) ?
    C15 C10 S1 . . 120.2(3) ?
    C11 C10 S1 . . 121.4(3) ?
    C10 C11 C12 . . 121.2(3) ?
    C10 C11 H11 . . 119.4 ?
    C12 C11 H11 . . 119.4 ?
    C13 C12 C11 . . 119.8(3) ?
    C13 C12 H12 . . 120.1 ?
    C11 C12 H12 . . 120.1 ?
    C12 C13 O3 . . 125.3(3) ?
    C12 C13 C14 . . 119.5(4) ?
    O3 C13 C14 . . 115.2(3) ?
    C15 C14 C13 . . 120.3(4) ?
    C15 C14 H14 . . 119.8 ?
    C13 C14 H14 . . 119.8 ?
    C14 C15 C10 . . 120.8(3) ?
    C14 C15 H15 . . 119.6 ?
    C10 C15 H15 . . 119.6 ?
    O3 C16 H16A . . 109.5 ?
    O3 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O3 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 0.9(6) ?
    C1 C2 C3 C4 . . . . -0.5(5) ?
    C2 C3 C4 C5 . . . . -1.1(5) ?
    C2 C3 C4 C7 . . . . -179.6(3) ?
    C3 C4 C5 C6 . . . . 2.2(5) ?
    C7 C4 C5 C6 . . . . -179.3(3) ?
    C2 C1 C6 C5 . . . . 0.2(6) ?
    C4 C5 C6 C1 . . . . -1.9(6) ?
    C5 C4 C7 O1 . . . . -179.3(3) ?
    C3 C4 C7 O1 . . . . -0.8(4) ?
    C5 C4 C7 C8 . . . . 2.1(4) ?
    C3 C4 C7 C8 . . . . -179.4(3) ?
    C9 O2 C8 C7 . . . . 161.9(3) ?
    C9 O2 C8 S1 . . . . -76.7(3) ?
    O1 C7 C8 O2 . . . . 19.8(4) ?
    C4 C7 C8 O2 . . . . -161.5(2) ?
    O1 C7 C8 S1 . . . . -104.5(3) ?
    C4 C7 C8 S1 . . . . 74.1(3) ?
    C10 S1 C8 O2 . . . . -74.0(3) ?
    C10 S1 C8 C7 . . . . 46.6(3) ?
    C8 S1 C10 C15 . . . . -101.2(3) ?
    C8 S1 C10 C11 . . . . 81.4(3) ?
    C15 C10 C11 C12 . . . . 0.6(4) ?
    S1 C10 C11 C12 . . . . 178.0(2) ?
    C10 C11 C12 C13 . . . . -0.5(5) ?
    C11 C12 C13 O3 . . . . -179.7(3) ?
    C11 C12 C13 C14 . . . . 0.2(5) ?
    C16 O3 C13 C12 . . . . -1.1(5) ?
    C16 O3 C13 C14 . . . . 179.1(3) ?
    C12 C13 C14 C15 . . . . 0.1(5) ?
    O3 C13 C14 C15 . . . . 179.9(3) ?
    C13 C14 C15 C10 . . . . 0.0(5) ?
    C11 C10 C15 C14 . . . . -0.3(5) ?
    S1 C10 C15 C14 . . . . -177.8(3) ?
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
    C8 H8 O1 2_664 0.98 2.54 3.406(5) 147
    C16 H16C O1 2_665 0.96 2.47 3.421(5) 170
data_New_Global_Publ_Block
_journal_date_recd_electronic     2015-07-27
_journal_date_accepted     2015-08-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      9
_journal_page_first     o657
_journal_page_last     o658
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015014565
_journal_coeditor_code     HG5455
_publ_contact_author_name     'Ignez Caracelli'
_publ_contact_author_address
;
Departmento de Física
Universidade Federal de São Carlos,
13565-905 São Carlos
SP
Brazil
;
_publ_contact_author_email     'ignez@ufscar.br'
_publ_contact_author_fax     '551633518350'
_publ_contact_author_phone     '551633519741'
_publ_section_title
;
Crystal structure of 2-methoxy-2-[(4-methoxyphenyl)sulfanyl]-1-phenylethanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Caracelli, Ignez' .
;
Departmento de Física
Universidade Federal de São Carlos,
13565-905 São Carlos
SP
Brazil
;
    'Olivato, Paulo R.' .
;
Instituto de Química
Universidade de São Paulo
05508-000 São Paulo, SP
Brazil
;
    'Traesel, Henrique J.' .
;
Instituto de Química
Universidade de São Paulo
05508-000 São Paulo, SP
Brazil
;
    'Valença, Jéssica' .
;
Instituto de Química
Universidade de São Paulo
05508-000 São Paulo, SP
Brazil
;
    'Rodrigues, Daniel N. S.' .
;
Instituto de Química
Universidade de São Paulo
05508-000 São Paulo, SP
Brazil
;
    'Tiekink, Edward R.T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur,
Malaysia
;

