#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/02/2240269.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2240269
loop_
_publ_author_name
'Zukerman-Schpector, Julio'
'Olivato, Paulo R.'
'Traesel, Henrique J.'
'Valença, Jéssica'
'Rodrigues, Daniel N. S.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure of
 2-methoxy-2-[(4-methylphenyl)sulfanyl]-1-phenylethan-1-one
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3
_journal_page_last               o4
_journal_paper_doi               10.1107/S205698901402550X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H16 O2 S'
_chemical_formula_moiety         'C16 H16 O2 S'
_chemical_formula_sum            'C16 H16 O2 S'
_chemical_formula_weight         272.35
_chemical_name_common
;
2-Methoxy-2-[(4-methylphenyl)sulfanyl]-1-phenylethan-1-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8579(9)
_cell_length_b                   8.1257(4)
_cell_length_c                   9.8317(5)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.73
_cell_measurement_theta_min      3.08
_cell_volume                     1426.66(12)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR (Burla et al.,  2014
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5399
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.410
_diffrn_reflns_theta_min         2.754
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.147
_refine_ls_abs_structure_details
;
Flack x determined using 552 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0685
_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
'w=1/[σ²(Fo²)+(0.0294P)²+0.2164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                1648
_reflns_number_total             2337
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5421sup1.cif
_cod_data_source_block           I
_cod_database_code               2240269
_cod_database_fobs_code          2240269
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.853
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
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'
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
C C1 0.3662(3) 0.6856(7) 1.3764(5) 0.0916(18) Uani d 1
H H1A 0.3249 0.7532 1.4046 0.137 Uiso calc 1
H H1B 0.4106 0.7185 1.4243 0.137 Uiso calc 1
H H1C 0.3553 0.5725 1.3964 0.137 Uiso calc 1
C C2 0.3784(3) 0.7055(6) 1.2258(5) 0.0642(13) Uani d 1
C C3 0.3285(3) 0.7876(6) 1.1440(6) 0.0737(14) Uani d 1
H H3 0.2850 0.8300 1.1823 0.088 Uiso calc 1
C C4 0.3411(3) 0.8094(6) 1.0061(5) 0.0683(13) Uani d 1
H H4 0.3066 0.8670 0.9537 0.082 Uiso calc 1
C C5 0.4049(2) 0.7455(5) 0.9462(5) 0.0564(11) Uani d 1
C C6 0.4553(2) 0.6622(5) 1.0273(5) 0.0615(12) Uani d 1
H H6 0.4987 0.6186 0.9893 0.074 Uiso calc 1
C C7 0.4416(3) 0.6434(5) 1.1643(5) 0.0635(13) Uani d 1
H H7 0.4763 0.5868 1.2171 0.076 Uiso calc 1
C C8 0.4839(2) 0.9437(5) 0.7603(5) 0.0576(10) Uani d 1
H H8 0.4930 0.9708 0.6646 0.069 Uiso calc 1
C C9 0.6015(3) 0.8116(6) 0.7474(6) 0.0834(15) Uani d 1
H H9A 0.6139 0.8637 0.6627 0.125 Uiso calc 1
H H9B 0.5771 0.7085 0.7299 0.125 Uiso calc 1
H H9C 0.6465 0.7927 0.7987 0.125 Uiso calc 1
C C10 0.4468(2) 1.0888(5) 0.8275(5) 0.0559(11) Uani d 1
C C11 0.3852(2) 1.1782(5) 0.7587(5) 0.0539(10) Uani d 1
C C12 0.3573(2) 1.3181(5) 0.8205(5) 0.0674(13) Uani d 1
H H12 0.3767 1.3519 0.9037 0.081 Uiso calc 1
C C13 0.3007(3) 1.4083(5) 0.7595(7) 0.0793(14) Uani d 1
H H13 0.2828 1.5027 0.8021 0.095 Uiso calc 1
C C14 0.2709(3) 1.3608(6) 0.6381(7) 0.0781(14) Uani d 1
H H14 0.2325 1.4212 0.5983 0.094 Uiso calc 1
C C15 0.2984(3) 1.2225(7) 0.5754(5) 0.0840(16) Uani d 1
H H15 0.2780 1.1887 0.4930 0.101 Uiso calc 1
C C16 0.3556(3) 1.1333(6) 0.6325(5) 0.0736(13) Uani d 1
H H16 0.3748 1.0423 0.5868 0.088 Uiso calc 1
O O1 0.55239(15) 0.9162(4) 0.8235(3) 0.0666(9) Uani d 1
O O2 0.46803(18) 1.1328(4) 0.9400(3) 0.0727(9) Uani d 1
S S 0.41986(7) 0.76542(13) 0.76791(16) 0.0711(4) Uani d 1
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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C7 116.9(5)
C3 C2 C1 122.3(5)
C7 C2 C1 120.8(5)
C2 C3 C4 122.0(5)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 120.2(5)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 118.4(5)
C6 C5 S 121.0(4)
C4 C5 S 120.6(4)
C7 C6 C5 120.2(5)
C7 C6 H6 119.9
C5 C6 H6 119.9
C2 C7 C6 122.3(5)
C2 C7 H7 118.8
C6 C7 H7 118.8
O1 C8 C10 108.5(4)
O1 C8 S 113.6(3)
C10 C8 S 108.9(3)
O1 C8 H8 108.6
C10 C8 H8 108.6
S C8 H8 108.6
O1 C9 H9A 109.5
O1 C9 H9B 109.5
H9A C9 H9B 109.5
O1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C10 C11 120.0(4)
O2 C10 C8 119.2(4)
C11 C10 C8 120.7(4)
C12 C11 C16 117.9(4)
C12 C11 C10 118.1(4)
C16 C11 C10 123.9(4)
C11 C12 C13 120.6(5)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 120.9(5)
C14 C13 H13 119.5
C12 C13 H13 119.5
C13 C14 C15 119.0(5)
C13 C14 H14 120.5
C15 C14 H14 120.5
C16 C15 C14 121.0(5)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C11 120.4(5)
C15 C16 H16 119.8
C11 C16 H16 119.8
C8 O1 C9 113.7(3)
C5 S C8 101.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.505(7)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.373(7)
C2 C7 1.376(6)
C3 C4 1.385(7)
C3 H3 0.9300
C4 C5 1.383(6)
C4 H4 0.9300
C5 C6 1.379(6)
C5 S 1.781(5)
C6 C7 1.378(6)
C6 H6 0.9300
C7 H7 0.9300
C8 O1 1.390(4)
C8 C10 1.505(5)
C8 S 1.847(4)
C8 H8 0.9800
C9 O1 1.432(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 O2 1.224(5)
C10 C11 1.480(6)
C11 C12 1.382(6)
C11 C16 1.398(7)
C12 C13 1.384(6)
C12 H12 0.9300
C13 C14 1.363(8)
C13 H13 0.9300
C14 C15 1.373(6)
C14 H14 0.9300
C15 C16 1.372(6)
C15 H15 0.9300
C16 H16 0.9300
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
C1 H1B O2 2_675 0.96 2.49 3.366(6) 152
C8 H8 O2 2_674 0.98 2.46 3.323(6) 146
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
C7 C2 C3 C4 -0.8(7)
C1 C2 C3 C4 178.2(4)
C2 C3 C4 C5 1.0(7)
C3 C4 C5 C6 -0.7(6)
C3 C4 C5 S 177.5(4)
C4 C5 C6 C7 0.3(6)
S C5 C6 C7 -177.9(4)
C3 C2 C7 C6 0.3(7)
C1 C2 C7 C6 -178.7(4)
C5 C6 C7 C2 0.0(7)
O1 C8 C10 O2 -18.2(5)
S C8 C10 O2 105.9(4)
O1 C8 C10 C11 161.7(3)
S C8 C10 C11 -74.1(4)
O2 C10 C11 C12 4.9(6)
C8 C10 C11 C12 -175.0(4)
O2 C10 C11 C16 -177.7(4)
C8 C10 C11 C16 2.3(6)
C16 C11 C12 C13 1.2(6)
C10 C11 C12 C13 178.7(4)
C11 C12 C13 C14 0.5(7)
C12 C13 C14 C15 -0.8(7)
C13 C14 C15 C16 -0.6(8)
C14 C15 C16 C11 2.4(8)
C12 C11 C16 C15 -2.7(7)
C10 C11 C16 C15 180.0(4)
C10 C8 O1 C9 -164.3(3)
S C8 O1 C9 74.4(4)
C6 C5 S C8 -83.1(4)
C4 C5 S C8 98.8(4)
O1 C8 S C5 63.2(4)
C10 C8 S C5 -57.9(3)
