#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:11:52 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180172 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/68/7106816.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_7106816
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         'C13 H13 Br O S'
_chemical_formula_sum            'C13 H13 Br O S'
_chemical_formula_weight         297.20
_chemical_name_common            2-(2-bromophenylthio)-3-methyl-2-cyclohexenone
_chemical_name_systematic
;
2-(2-bromophenylthio)-3-methyl-2-cyclohexenone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-11-17T15:05:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.730(5)
_cell_length_b                   15.142(5)
_cell_length_c                   20.590(6)
_cell_measurement_reflns_used    7112
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.98
_cell_volume                     4904(3)
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28443
_diffrn_reflns_theta_full        27.9
_diffrn_reflns_theta_max         27.9
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    3.498
_exptl_absorpt_correction_T_max  0.5413
_exptl_absorpt_correction_T_min  0.3351
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS ver 2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.61
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0345
_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)+(0.0387P)²+2.8425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                4446
_reflns_number_total             5696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13484a.txt
_cod_data_source_block           compound_3
_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_sg_symbol_H-M      Pbca
_cod_database_code               7106816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.184659(18) 0.32073(2) 0.209111(12) 0.03087(9) Uani 1 1 d . . .
Br2 Br 0.89007(2) 0.043172(18) 0.554879(12) 0.03595(10) Uani 1 1 d . . .
S1 S 0.16057(4) 0.31618(4) 0.36308(3) 0.02151(14) Uani 1 1 d . . .
S2 S 0.86853(5) 0.04137(4) 0.40099(3) 0.02914(17) Uani 1 1 d . . .
C25 C 0.76761(16) 0.06280(16) 0.29192(12) 0.0217(5) Uani 1 1 d . . .
C14 C 0.85847(15) 0.14652(16) 0.50854(11) 0.0174(5) Uani 1 1 d . . .
C19 C 0.84967(16) 0.14285(16) 0.44154(11) 0.0181(5) Uani 1 1 d . . .
C18 C 0.82650(15) 0.22052(16) 0.40983(12) 0.0204(5) Uani 1 1 d . . .
H18 H 0.8198 0.2203 0.364 0.024 Uiso 1 1 calc R . .
O1 O 0.14840(13) 0.49460(11) 0.41977(8) 0.0277(4) Uani 1 1 d . . .
C22 C 0.91020(17) 0.11407(17) 0.20975(12) 0.0236(5) Uani 1 1 d . . .
H22A H 0.928 0.0619 0.1841 0.028 Uiso 1 1 calc R . .
H22B H 0.9479 0.1638 0.1977 0.028 Uiso 1 1 calc R . .
O2 O 0.70591(12) 0.05167(14) 0.32663(9) 0.0355(5) Uani 1 1 d . . .
C7 C 0.12715(15) 0.34348(16) 0.44320(11) 0.0174(5) Uani 1 1 d . . .
C1 C 0.07788(15) 0.34626(15) 0.24839(11) 0.0185(5) Uani 1 1 d . . .
C20 C 0.85533(16) 0.07032(15) 0.31797(11) 0.0185(5) Uani 1 1 d . . .
C11 C 0.08375(18) 0.30583(18) 0.55571(12) 0.0261(6) Uani 1 1 d . . .
H11A H 0.1338 0.2939 0.5835 0.031 Uiso 1 1 calc R . .
H11B H 0.0368 0.2675 0.5709 0.031 Uiso 1 1 calc R . .
C2 C 0.00964(17) 0.36530(16) 0.20827(12) 0.0229(5) Uani 1 1 d . . .
H2 H 0.0165 0.365 0.1624 0.028 Uiso 1 1 calc R . .
C13 C 0.09955(18) 0.18422(17) 0.47237(15) 0.0317(6) Uani 1 1 d . . .
H13A H 0.0397 0.167 0.4687 0.048 Uiso 1 1 calc R . .
H13B H 0.1263 0.1508 0.5076 0.048 Uiso 1 1 calc R . .
H13C H 0.1289 0.1715 0.4314 0.048 Uiso 1 1 calc R . .
C9 C 0.12124(17) 0.46174(16) 0.53109(12) 0.0223(5) Uani 1 1 d . . .
H9A H 0.1011 0.5235 0.5344 0.027 Uiso 1 1 calc R . .
H9B H 0.1766 0.4578 0.5538 0.027 Uiso 1 1 calc R . .
C12 C 0.10533(15) 0.28120(16) 0.48674(12) 0.0209(5) Uani 1 1 d . . .
C15 C 0.84632(16) 0.22359(17) 0.54308(11) 0.0207(5) Uani 1 1 d . . .
H15 H 0.8535 0.224 0.5889 0.025 Uiso 1 1 calc R . .
C6 C 0.07084(15) 0.34593(15) 0.31570(11) 0.0172(5) Uani 1 1 d . . .
C21 C 0.92193(16) 0.09407(15) 0.28078(12) 0.0203(5) Uani 1 1 d . . .
C16 C 0.82367(17) 0.30022(17) 0.51087(12) 0.0231(6) Uani 1 1 d . . .
H16 H 0.8155 0.3536 0.5342 0.028 Uiso 1 1 calc R . .
C10 C 0.05776(17) 0.40124(18) 0.56443(12) 0.0259(6) Uani 1 1 d . . .
H10A H 0.0552 0.4155 0.6113 0.031 Uiso 1 1 calc R . .
H10B H 0.0005 0.4106 0.5457 0.031 Uiso 1 1 calc R . .
C17 C 0.81303(17) 0.29810(16) 0.44404(12) 0.0231(5) Uani 1 1 d . . .
H17 H 0.7964 0.3501 0.4216 0.028 Uiso 1 1 calc R . .
C23 C 0.82011(17) 0.13750(18) 0.19180(12) 0.0260(6) Uani 1 1 d . . .
H23A H 0.8145 0.1398 0.1439 0.031 Uiso 1 1 calc R . .
H23B H 0.8058 0.1965 0.2094 0.031 Uiso 1 1 calc R . .
C5 C -0.00857(16) 0.36610(16) 0.34183(12) 0.0216(5) Uani 1 1 d . . .
H5 H -0.0155 0.3665 0.3877 0.026 Uiso 1 1 calc R . .
C26 C 1.01187(18) 0.10395(19) 0.30435(16) 0.0365(7) Uani 1 1 d . . .
H26A H 1.0251 0.1668 0.3098 0.055 Uiso 1 1 calc R . .
H26B H 1.0509 0.078 0.2725 0.055 Uiso 1 1 calc R . .
H26C H 1.0183 0.0735 0.3461 0.055 Uiso 1 1 calc R . .
C8 C 0.13348(16) 0.43844(16) 0.46046(11) 0.0185(5) Uani 1 1 d . . .
C24 C 0.75915(17) 0.06924(19) 0.21904(11) 0.0267(6) Uani 1 1 d . . .
H24A H 0.7001 0.0858 0.2077 0.032 Uiso 1 1 calc R . .
H24B H 0.7713 0.011 0.1993 0.032 Uiso 1 1 calc R . .
C3 C -0.06870(17) 0.38476(17) 0.23543(13) 0.0249(6) Uani 1 1 d . . .
H3 H -0.116 0.3974 0.2083 0.03 Uiso 1 1 calc R . .
C4 C -0.07775(16) 0.38564(17) 0.30244(13) 0.0244(6) Uani 1 1 d . . .
H4 H -0.1312 0.3996 0.3214 0.029 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'
Br Br -0.2901 2.4595 '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
C6 S1 C7 102.45(11) . . ?
C19 S2 C20 102.68(11) . . ?
O2 C25 C20 122.7(2) . . ?
O2 C25 C24 121.5(2) . . ?
C20 C25 C24 115.9(2) . . ?
C15 C14 C19 122.2(2) . . ?
C15 C14 Br2 118.31(17) . . ?
C19 C14 Br2 119.52(18) . . ?
C14 C19 C18 117.3(2) . . ?
C14 C19 S2 119.07(18) . . ?
C18 C19 S2 123.66(18) . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C21 C22 C23 113.6(2) . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C12 C7 C8 122.4(2) . . ?
C12 C7 S1 122.01(19) . . ?
C8 C7 S1 115.27(17) . . ?
C2 C1 C6 122.2(2) . . ?
C2 C1 Br1 118.21(18) . . ?
C6 C1 Br1 119.54(18) . . ?
C21 C20 C25 122.6(2) . . ?
C21 C20 S2 121.5(2) . . ?
C25 C20 S2 115.92(18) . . ?
C12 C11 C10 114.2(2) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C9 C10 112.2(2) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C7 C12 C13 124.7(2) . . ?
C7 C12 C11 120.8(2) . . ?
C13 C12 C11 114.5(2) . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C1 C6 C5 117.1(2) . . ?
C1 C6 S1 119.06(18) . . ?
C5 C6 S1 123.81(19) . . ?
C20 C21 C26 125.1(2) . . ?
C20 C21 C22 120.7(2) . . ?
C26 C21 C22 114.1(2) . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C11 C10 C9 110.2(2) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C22 C23 C24 110.1(2) . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.2 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 C8 C7 121.7(2) . . ?
O1 C8 C9 121.7(2) . . ?
C7 C8 C9 116.7(2) . . ?
C25 C24 C23 110.8(2) . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
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
Br1 C1 1.904(2) . ?
Br2 C14 1.899(2) . ?
S1 C6 1.774(2) . ?
S1 C7 1.780(2) . ?
S2 C19 1.774(2) . ?
S2 C20 1.777(2) . ?
C25 O2 1.217(3) . ?
C25 C20 1.485(4) . ?
C25 C24 1.510(3) . ?
C14 C15 1.380(3) . ?
C14 C19 1.388(3) . ?
C19 C18 1.393(3) . ?
C18 C17 1.386(3) . ?
C18 H18 0.95 . ?
O1 C8 1.217(3) . ?
C22 C21 1.505(3) . ?
C22 C23 1.507(4) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C7 C12 1.346(3) . ?
C7 C8 1.484(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.390(3) . ?
C20 C21 1.346(4) . ?
C11 C12 1.507(4) . ?
C11 C10 1.512(4) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C2 C3 1.385(4) . ?
C2 H2 0.95 . ?
C13 C12 1.501(4) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C9 C8 1.509(3) . ?
C9 C10 1.519(4) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C15 C16 1.383(4) . ?
C15 H15 0.95 . ?
C6 C5 1.394(3) . ?
C21 C26 1.503(4) . ?
C16 C17 1.387(3) . ?
C16 H16 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C17 H17 0.95 . ?
C23 C24 1.517(4) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C5 C4 1.389(3) . ?
C5 H5 0.95 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C3 C4 1.387(3) . ?
C3 H3 0.95 . ?
C4 H4 0.95 . ?
