#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:11:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180172 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/68/7106814.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_7106814
loop_
_publ_author_name
'Ryo Sekiya'
'Reiko Kuroda'
_publ_section_title
;
 Controlling stereoselectivity of solid-state photoreactions by co-crystal
 formation
;
_journal_name_full               Chem.Commun.
_journal_page_first              10097
_journal_paper_doi               10.1039/c1cc13484a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C14 H16 O S'
_chemical_formula_sum            'C14 H16 O S'
_chemical_formula_weight         232.33
_chemical_name_common            2-(2-methylphenylthio)-3-methyl-2-cyclohexenone
_chemical_name_systematic
;
2-(2-methylphenylthio)-3-methyl-2-cyclohexenone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-11-17T16:36:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                91.07(3)
_cell_angle_beta                 102.32(3)
_cell_angle_gamma                104.43(3)
_cell_formula_units_Z            4
_cell_length_a                   7.9230(16)
_cell_length_b                   10.418(2)
_cell_length_c                   15.473(3)
_cell_measurement_reflns_used    5421
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      1.35
_cell_volume                     1204.9(5)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.91
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7394
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.82
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_correction_T_min  0.9087
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS ver 2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0423
_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)+(0.0604P)²+0.3422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                4521
_reflns_number_total             5205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13484a.txt
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to the built-in table from CIF Core 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_cell_volume        1204.9(4)
_cod_database_code               7106814
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.83123(5) 0.31551(4) 0.13737(3) 0.01980(12) Uani 1 1 d . . .
S1 S 0.40524(6) 0.28817(4) 0.44759(3) 0.02092(12) Uani 1 1 d . . .
O1 O 0.79452(17) 0.32100(12) 0.46265(8) 0.0271(3) Uani 1 1 d . . .
C1 C 0.3789(2) 0.14203(16) 0.37991(11) 0.0186(3) Uani 1 1 d . . .
C22 C 0.8190(2) 0.14324(15) 0.13852(11) 0.0185(3) Uani 1 1 d . . .
C13 C 0.4986(2) 0.51359(16) 0.36209(10) 0.0168(3) Uani 1 1 d . . .
C5 C 0.2794(2) -0.09614(17) 0.36010(13) 0.0258(4) Uani 1 1 d . . .
H5 H 0.2318 -0.1792 0.3815 0.031 Uiso 1 1 calc R . .
C8 C 0.5521(2) 0.41196(15) 0.40265(10) 0.0170(3) Uani 1 1 d . . .
C9 C 0.7412(2) 0.40391(16) 0.41787(11) 0.0191(3) Uani 1 1 d . . .
C12 C 0.6277(2) 0.62690(16) 0.33258(11) 0.0209(3) Uani 1 1 d . . .
H12A H 0.5991 0.711 0.3467 0.025 Uiso 1 1 calc R . .
H12B H 0.6106 0.6154 0.2674 0.025 Uiso 1 1 calc R . .
C15 C 1.0961(2) 0.52275(16) 0.10943(10) 0.0184(3) Uani 1 1 d . . .
C17 C 1.1749(2) 0.31187(16) 0.12353(11) 0.0203(3) Uani 1 1 d . . .
H17 H 1.1441 0.2201 0.1334 0.024 Uiso 1 1 calc R . .
C2 C 0.4201(2) 0.14432(17) 0.29675(11) 0.0218(3) Uani 1 1 d . . .
H2 H 0.4686 0.2269 0.275 0.026 Uiso 1 1 calc R . .
O2 O 0.7513(2) 0.11940(14) -0.01876(9) 0.0406(4) Uani 1 1 d . . .
C21 C 0.9674(2) 0.60660(16) 0.11293(11) 0.0223(4) Uani 1 1 d . . .
H21A H 1.0196 0.6972 0.0989 0.033 Uiso 1 1 calc R . .
H21B H 0.944 0.6087 0.1726 0.033 Uiso 1 1 calc R . .
H21C H 0.855 0.5684 0.0696 0.033 Uiso 1 1 calc R . .
C27 C 0.8461(2) 0.08402(16) 0.21567(11) 0.0195(3) Uani 1 1 d . . .
C6 C 0.3049(2) 0.02029(16) 0.41247(12) 0.0206(3) Uani 1 1 d . . .
C4 C 0.3216(2) -0.09391(18) 0.27747(13) 0.0285(4) Uani 1 1 d . . .
H4 H 0.3032 -0.1747 0.243 0.034 Uiso 1 1 calc R . .
C16 C 1.0501(2) 0.38550(16) 0.12170(10) 0.0173(3) Uani 1 1 d . . .
C19 C 1.3894(2) 0.50583(18) 0.09623(11) 0.0242(4) Uani 1 1 d . . .
H19 H 1.5043 0.5469 0.0864 0.029 Uiso 1 1 calc R . .
C11 C 0.8237(2) 0.63854(17) 0.37540(12) 0.0229(4) Uani 1 1 d . . .
H11A H 0.9013 0.6999 0.3433 0.027 Uiso 1 1 calc R . .
H11B H 0.8509 0.6755 0.4377 0.027 Uiso 1 1 calc R . .
C20 C 1.2657(2) 0.57985(17) 0.09576(11) 0.0223(4) Uani 1 1 d . . .
H20 H 1.2978 0.6716 0.0859 0.027 Uiso 1 1 calc R . .
C10 C 0.8617(2) 0.50262(17) 0.37287(12) 0.0236(4) Uani 1 1 d . . .
H10A H 0.8441 0.4694 0.3104 0.028 Uiso 1 1 calc R . .
H10B H 0.988 0.511 0.4027 0.028 Uiso 1 1 calc R . .
C26 C 0.8172(2) -0.06413(17) 0.21674(13) 0.0268(4) Uani 1 1 d . . .
H26A H 0.7576 -0.0952 0.2654 0.032 Uiso 1 1 calc R . .
H26B H 0.935 -0.0848 0.2296 0.032 Uiso 1 1 calc R . .
C7 C 0.2536(2) 0.01489(18) 0.50086(12) 0.0257(4) Uani 1 1 d . . .
H7A H 0.2049 -0.0779 0.5118 0.039 Uiso 1 1 calc R . .
H7B H 0.163 0.0641 0.5004 0.039 Uiso 1 1 calc R . .
H7C H 0.3595 0.0549 0.5478 0.039 Uiso 1 1 calc R . .
C23 C 0.7768(3) 0.06714(18) 0.05109(12) 0.0263(4) Uani 1 1 d . . .
C18 C 1.3449(2) 0.37206(17) 0.11102(11) 0.0234(4) Uani 1 1 d . . .
H18 H 1.4301 0.3216 0.1126 0.028 Uiso 1 1 calc R . .
C14 C 0.3098(2) 0.52461(17) 0.34308(12) 0.0222(4) Uani 1 1 d . . .
H14A H 0.2297 0.4386 0.3492 0.033 Uiso 1 1 calc R . .
H14B H 0.2773 0.5506 0.2825 0.033 Uiso 1 1 calc R . .
H14C H 0.2988 0.5919 0.3852 0.033 Uiso 1 1 calc R . .
C28 C 0.9070(2) 0.15710(19) 0.30505(12) 0.0272(4) Uani 1 1 d . . .
H28A H 0.9572 0.2516 0.299 0.041 Uiso 1 1 calc R . .
H28B H 0.9988 0.1211 0.3418 0.041 Uiso 1 1 calc R . .
H28C H 0.8052 0.1467 0.3332 0.041 Uiso 1 1 calc R . .
C3 C 0.3907(2) 0.02677(18) 0.24541(12) 0.0270(4) Uani 1 1 d . . .
H3 H 0.4179 0.029 0.1885 0.032 Uiso 1 1 calc R . .
C25 C 0.7054(3) -0.14003(18) 0.13058(14) 0.0329(4) Uani 1 1 d . . .
H25A H 0.7112 -0.2338 0.1312 0.039 Uiso 1 1 calc R . .
H25B H 0.579 -0.1385 0.1244 0.039 Uiso 1 1 calc R . .
C24 C 0.7738(3) -0.07802(19) 0.05282(14) 0.0370(5) Uani 1 1 d . . .
H24A H 0.8963 -0.0876 0.0564 0.044 Uiso 1 1 calc R . .
H24B H 0.6964 -0.1262 -0.0031 0.044 Uiso 1 1 calc R . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 S2 C16 102.99(8) . . ?
C8 S1 C1 103.54(8) . . ?
C2 C1 C6 120.30(15) . . ?
C2 C1 S1 123.07(13) . . ?
C6 C1 S1 116.56(13) . . ?
C27 C22 C23 121.70(15) . . ?
C27 C22 S2 121.42(13) . . ?
C23 C22 S2 116.88(13) . . ?
C8 C13 C14 123.84(15) . . ?
C8 C13 C12 121.93(15) . . ?
C14 C13 C12 114.22(14) . . ?
C4 C5 C6 121.72(17) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C13 C8 C9 121.69(15) . . ?
C13 C8 S1 121.79(13) . . ?
C9 C8 S1 116.37(12) . . ?
O1 C9 C8 122.00(16) . . ?
O1 C9 C10 121.99(15) . . ?
C8 C9 C10 116.00(14) . . ?
C13 C12 C11 114.00(14) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.6 . . ?
C20 C15 C16 118.17(15) . . ?
C20 C15 C21 120.46(15) . . ?
C16 C15 C21 121.35(15) . . ?
C16 C17 C18 120.33(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C3 C2 C1 120.47(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C27 C28 124.09(16) . . ?
C22 C27 C26 121.43(16) . . ?
C28 C27 C26 114.48(15) . . ?
C5 C6 C1 117.96(16) . . ?
C5 C6 C7 120.50(16) . . ?
C1 C6 C7 121.54(15) . . ?
C3 C4 C5 119.70(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C17 C16 C15 120.28(15) . . ?
C17 C16 S2 122.79(13) . . ?
C15 C16 S2 116.91(13) . . ?
C18 C19 C20 119.93(16) . . ?
C18 C19 H19 120 . . ?
C20 C19 H19 120 . . ?
C10 C11 C12 110.09(14) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C19 C20 C15 121.49(16) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C9 C10 C11 111.64(14) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
C27 C26 C25 113.69(15) . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C23 C22 122.20(16) . . ?
O2 C23 C24 121.30(17) . . ?
C22 C23 C24 116.45(16) . . ?
C19 C18 C17 119.75(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C3 C2 119.83(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C24 C25 C26 110.09(16) . . ?
C24 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
C24 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
H25A C25 H25B 108.2 . . ?
C23 C24 C25 112.07(16) . . ?
C23 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C22 1.7737(17) . ?
S2 C16 1.7759(17) . ?
S1 C8 1.7695(17) . ?
S1 C1 1.7740(17) . ?
O1 C9 1.218(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.409(2) . ?
C22 C27 1.355(2) . ?
C22 C23 1.485(2) . ?
C13 C8 1.352(2) . ?
C13 C14 1.496(2) . ?
C13 C12 1.505(2) . ?
C5 C4 1.388(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.95 . ?
C8 C9 1.490(2) . ?
C9 C10 1.508(2) . ?
C12 C11 1.526(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C15 C20 1.390(2) . ?
C15 C16 1.412(2) . ?
C15 C21 1.507(2) . ?
C17 C16 1.391(2) . ?
C17 C18 1.393(2) . ?
C17 H17 0.95 . ?
C2 C3 1.388(2) . ?
C2 H2 0.95 . ?
O2 C23 1.220(2) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C27 C28 1.489(2) . ?
C27 C26 1.504(2) . ?
C6 C7 1.506(2) . ?
C4 C3 1.387(3) . ?
C4 H4 0.95 . ?
C19 C18 1.386(2) . ?
C19 C20 1.389(3) . ?
C19 H19 0.95 . ?
C11 C10 1.521(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C20 H20 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C26 C25 1.515(3) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C23 C24 1.507(3) . ?
C18 H18 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C3 H3 0.95 . ?
C25 C24 1.514(3) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
