#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:01:21 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244608 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239228.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_7239228
loop_
_publ_author_name
'Fuchs, Christian'
'Edgar, Mark'
'Elsegood, Mark R. J.'
'Weaver, George W.'
_publ_section_title
;
 Studies on the double alkylation of
 2,2-disubstituted-1,3-dithiacycloalkane-S-oxides: synthesis of tertiary
 thiol derivatives
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              21911
_journal_paper_doi               10.1039/c3ra43688h
_journal_volume                  3
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H24 O S2'
_chemical_formula_sum            'C13 H24 O S2'
_chemical_formula_weight         260.44
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.2784(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1567(6)
_cell_length_b                   6.6861(5)
_cell_length_c                   12.7905(10)
_cell_measurement_reflns_used    4348
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.81
_cell_volume                     691.93(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6972
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0263
_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/[\s^2^(Fo^2^)+(0.0421P)^2^+0.0247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0665
_reflns_number_gt                3240
_reflns_number_total             3367
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3ra43688h.txt
_cod_data_source_block           23
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7239228
_iucr_refine_instruction_details
;
TITL gw50 in P2(1)
CELL 0.71073 8.1567 6.6861 12.7905 90.000 97.2784 90.000
ZERR 2.00 0.0006 0.0005 0.0010 0.000 0.0011 0.000
LATT -1
SYMM -X, 0.5+Y, -Z
SFAC C H O S
UNIT 26 48 2 4
TEMP -123
SIZE 0.06 0.19 0.56

ACTA
CONF
WPDB -1

L.S. 4
BOND
FMAP 2
PLAN 10

REM EXTI 0.000000 INSIGNIFICANT
WGHT 0.042100 0.024700
FVAR 0.45501
O1 3 0.914225 -0.272828 0.145807 11.00000 0.03441 0.02241 =
0.03355 0.00283 0.00906 0.00940
S1 4 0.769096 -0.143172 0.106786 11.00000 0.02389 0.01710 =
0.02084 -0.00159 0.00623 0.00069
C2 1 0.762831 0.067642 0.200557 11.00000 0.01944 0.01638 =
0.01776 -0.00149 0.00233 0.00137
S3 4 0.601153 0.231509 0.137016 11.00000 0.01983 0.02173 =
0.02226 0.00093 0.00277 0.00403
C4 1 0.694239 0.319883 0.024119 11.00000 0.02543 0.02296 =
0.02366 0.00675 0.00291 0.00051
AFIX 23
H4A 2 0.621832 0.422909 -0.013235 11.00000 -1.20000
H4B 2 0.801701 0.383515 0.049036 11.00000 -1.20000
AFIX 0
C5 1 0.721520 0.153529 -0.052319 11.00000 0.02748 0.02714 =
0.02066 0.00346 0.00384 0.00004
AFIX 23
H5A 2 0.768678 0.211602 -0.113159 11.00000 -1.20000
H5B 2 0.613292 0.093766 -0.079170 11.00000 -1.20000
AFIX 0
C6 1 0.835511 -0.010504 -0.004307 11.00000 0.03041 0.02427 =
0.01993 0.00039 0.00920 0.00228
AFIX 23
H6A 2 0.945190 0.049300 0.018694 11.00000 -1.20000
H6B 2 0.849882 -0.109239 -0.060107 11.00000 -1.20000
AFIX 0
C7 1 0.713932 -0.022715 0.304606 11.00000 0.02249 0.01855 =
0.02103 0.00107 0.00467 0.00087
AFIX 13
H7 2 0.805526 -0.117049 0.330000 11.00000 -1.20000
AFIX 0
C8 1 0.720054 0.139817 0.389747 11.00000 0.03059 0.02361 =
0.01860 0.00033 0.00572 -0.00117
AFIX 23
H8A 2 0.634917 0.242121 0.367683 11.00000 -1.20000
H8B 2 0.693697 0.079167 0.456230 11.00000 -1.20000
AFIX 0
C9 1 0.888518 0.240278 0.409455 11.00000 0.03443 0.02515 =
0.01908 -0.00250 -0.00013 -0.00465
AFIX 23
H9A 2 0.972254 0.140778 0.438125 11.00000 -1.20000
H9B 2 0.885289 0.347329 0.462629 11.00000 -1.20000
AFIX 0
C10 1 0.938767 0.330008 0.308350 11.00000 0.02551 0.02049 =
0.02151 0.00102 -0.00082 -0.00272
AFIX 13
H10 2 0.856677 0.435966 0.283058 11.00000 -1.20000
AFIX 0
C11 1 0.932417 0.167704 0.223459 11.00000 0.01771 0.02218 =
0.02109 0.00095 0.00184 -0.00039
AFIX 23
H11A 2 0.961678 0.228013 0.157599 11.00000 -1.20000
H11B 2 1.016192 0.064316 0.246404 11.00000 -1.20000
AFIX 0
C12 1 0.554532 -0.150081 0.297144 11.00000 0.02933 0.02696 =
0.02662 -0.00442 0.01169 -0.00644
AFIX 13
H12 2 0.543739 -0.222673 0.228257 11.00000 -1.20000
AFIX 0
C13 1 0.571786 -0.307647 0.384849 11.00000 0.04062 0.02333 =
0.06149 0.00975 0.02248 0.00011
AFIX 137
H13A 2 0.580781 -0.240967 0.453570 11.00000 -1.50000
H13B 2 0.671182 -0.387902 0.380344 11.00000 -1.50000
H13C 2 0.474428 -0.394843 0.376724 11.00000 -1.50000
AFIX 0
C14 1 0.394498 -0.034807 0.301980 11.00000 0.02503 0.04282 =
0.04074 0.00334 0.00838 -0.00285
AFIX 137
H14A 2 0.300911 -0.127828 0.293285 11.00000 -1.50000
H14B 2 0.380692 0.064991 0.245433 11.00000 -1.50000
H14C 2 0.398975 0.032548 0.370333 11.00000 -1.50000
AFIX 0
C15 1 1.109731 0.426205 0.326240 11.00000 0.02956 0.03104 =
0.02709 -0.00060 -0.00205 -0.00746
AFIX 137
H15A 2 1.108905 0.536472 0.376649 11.00000 -1.50000
H15B 2 1.138605 0.477765 0.259215 11.00000 -1.50000
H15C 2 1.191449 0.326140 0.354342 11.00000 -1.50000

HKLF 4

REM gw50 in P2(1)
REM R1 = 0.0263 for 3240 Fo > 4sig(Fo) and 0.0279 for all 3367 data
REM 148 parameters refined using 1 restraints

END

WGHT 0.0420 0.0246
REM Highest difference peak 0.321, deepest hole -0.185, 1-sigma level 0.042
Q1 1 0.6265 0.2629 0.0773 11.00000 0.05 0.32
Q2 1 0.9386 0.2412 0.2631 11.00000 0.05 0.29
Q3 1 0.7814 -0.0216 0.1613 11.00000 0.05 0.26
Q4 1 0.7752 -0.0955 0.0471 11.00000 0.05 0.26
Q5 1 0.8605 0.1120 0.2166 11.00000 0.05 0.25
Q6 1 0.7513 0.0208 0.2557 11.00000 0.05 0.24
Q7 1 0.4905 0.2277 0.1237 11.00000 0.05 0.24
Q8 1 0.7137 0.2300 -0.0124 11.00000 0.05 0.23
Q9 1 0.6577 -0.1541 0.0954 11.00000 0.05 0.23
Q10 1 0.9099 0.2744 0.3591 11.00000 0.05 0.22
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 O 0.91423(13) -0.27283(18) 0.14581(9) 0.0297(2) Uani 1 1 d .
S1 S 0.76910(4) -0.14317(5) 0.10679(3) 0.02032(9) Uani 1 1 d .
C2 C 0.76283(17) 0.0676(2) 0.20056(10) 0.0179(3) Uani 1 1 d .
S3 S 0.60115(4) 0.23151(5) 0.13702(3) 0.02126(9) Uani 1 1 d .
C4 C 0.69424(18) 0.3199(2) 0.02412(11) 0.0240(3) Uani 1 1 d .
H4A H 0.6218 0.4229 -0.0132 0.029 Uiso 1 1 calc R
H4B H 0.8017 0.3835 0.0490 0.029 Uiso 1 1 calc R
C5 C 0.7215(2) 0.1535(2) -0.05232(12) 0.0250(3) Uani 1 1 d .
H5A H 0.7687 0.2116 -0.1132 0.030 Uiso 1 1 calc R
H5B H 0.6133 0.0938 -0.0792 0.030 Uiso 1 1 calc R
C6 C 0.83551(19) -0.0105(2) -0.00431(11) 0.0244(3) Uani 1 1 d .
H6A H 0.9452 0.0493 0.0187 0.029 Uiso 1 1 calc R
H6B H 0.8499 -0.1092 -0.0601 0.029 Uiso 1 1 calc R
C7 C 0.71393(18) -0.0227(2) 0.30461(11) 0.0205(3) Uani 1 1 d .
H7 H 0.8055 -0.1170 0.3300 0.025 Uiso 1 1 calc R
C8 C 0.72005(18) 0.1398(2) 0.38975(11) 0.0240(3) Uani 1 1 d .
H8A H 0.6349 0.2421 0.3677 0.029 Uiso 1 1 calc R
H8B H 0.6937 0.0792 0.4562 0.029 Uiso 1 1 calc R
C9 C 0.88852(19) 0.2403(3) 0.40945(11) 0.0265(3) Uani 1 1 d .
H9A H 0.9723 0.1408 0.4381 0.032 Uiso 1 1 calc R
H9B H 0.8853 0.3473 0.4626 0.032 Uiso 1 1 calc R
C10 C 0.93877(18) 0.3300(2) 0.30835(11) 0.0228(3) Uani 1 1 d .
H10 H 0.8567 0.4360 0.2831 0.027 Uiso 1 1 calc R
C11 C 0.93242(17) 0.1677(2) 0.22346(11) 0.0204(3) Uani 1 1 d .
H11A H 0.9617 0.2280 0.1576 0.024 Uiso 1 1 calc R
H11B H 1.0162 0.0643 0.2464 0.024 Uiso 1 1 calc R
C12 C 0.55453(18) -0.1501(3) 0.29714(12) 0.0269(3) Uani 1 1 d .
H12 H 0.5437 -0.2227 0.2283 0.032 Uiso 1 1 calc R
C13 C 0.5718(2) -0.3076(3) 0.38485(17) 0.0404(4) Uani 1 1 d .
H13A H 0.5808 -0.2410 0.4536 0.061 Uiso 1 1 calc R
H13B H 0.6712 -0.3879 0.3803 0.061 Uiso 1 1 calc R
H13C H 0.4744 -0.3948 0.3767 0.061 Uiso 1 1 calc R
C14 C 0.3945(2) -0.0348(3) 0.30198(15) 0.0358(4) Uani 1 1 d .
H14A H 0.3009 -0.1278 0.2933 0.054 Uiso 1 1 calc R
H14B H 0.3807 0.0650 0.2454 0.054 Uiso 1 1 calc R
H14C H 0.3990 0.0325 0.3703 0.054 Uiso 1 1 calc R
C15 C 1.1097(2) 0.4262(3) 0.32624(13) 0.0297(3) Uani 1 1 d .
H15A H 1.1089 0.5365 0.3766 0.045 Uiso 1 1 calc R
H15B H 1.1386 0.4778 0.2592 0.045 Uiso 1 1 calc R
H15C H 1.1914 0.3261 0.3543 0.045 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0344(6) 0.0224(5) 0.0335(6) 0.0028(5) 0.0091(4) 0.0094(5)
S1 0.02389(17) 0.01710(15) 0.02084(16) -0.00159(13) 0.00623(12) 0.00069(13)
C2 0.0194(7) 0.0164(6) 0.0178(6) -0.0015(5) 0.0023(5) 0.0014(5)
S3 0.01983(16) 0.02173(16) 0.02226(17) 0.00093(14) 0.00277(12) 0.00403(14)
C4 0.0254(7) 0.0230(8) 0.0237(7) 0.0067(6) 0.0029(5) 0.0005(6)
C5 0.0275(7) 0.0271(8) 0.0207(7) 0.0035(6) 0.0038(6) 0.0000(6)
C6 0.0304(8) 0.0243(7) 0.0199(7) 0.0004(6) 0.0092(6) 0.0023(6)
C7 0.0225(7) 0.0185(6) 0.0210(7) 0.0011(5) 0.0047(5) 0.0009(5)
C8 0.0306(8) 0.0236(8) 0.0186(6) 0.0003(6) 0.0057(6) -0.0012(6)
C9 0.0344(8) 0.0252(7) 0.0191(6) -0.0025(6) -0.0001(5) -0.0047(7)
C10 0.0255(7) 0.0205(7) 0.0215(6) 0.0010(6) -0.0008(5) -0.0027(6)
C11 0.0177(6) 0.0222(7) 0.0211(6) 0.0010(5) 0.0018(5) -0.0004(5)
C12 0.0293(7) 0.0270(7) 0.0266(7) -0.0044(7) 0.0117(6) -0.0064(7)
C13 0.0406(10) 0.0233(9) 0.0615(12) 0.0098(8) 0.0225(9) 0.0001(7)
C14 0.0250(8) 0.0428(10) 0.0407(9) 0.0033(8) 0.0084(7) -0.0029(8)
C15 0.0296(8) 0.0310(8) 0.0271(8) -0.0006(6) -0.0020(6) -0.0075(6)
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
O1 S1 C6 103.98(7)
O1 S1 C2 108.00(6)
C6 S1 C2 99.80(7)
C11 C2 C7 109.19(11)
C11 C2 S3 114.04(10)
C7 C2 S3 111.37(9)
C11 C2 S1 110.94(9)
C7 C2 S1 106.76(9)
S3 C2 S1 104.23(7)
C4 S3 C2 101.45(6)
C5 C4 S3 112.64(10)
C4 C5 C6 113.71(12)
C5 C6 S1 116.23(10)
C8 C7 C12 112.65(12)
C8 C7 C2 110.03(12)
C12 C7 C2 117.69(12)
C9 C8 C7 112.19(12)
C8 C9 C10 111.51(12)
C15 C10 C9 112.12(12)
C15 C10 C11 110.68(12)
C9 C10 C11 109.47(12)
C2 C11 C10 113.20(11)
C14 C12 C13 108.52(13)
C14 C12 C7 115.89(14)
C13 C12 C7 109.56(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 S1 1.5007(11)
S1 C6 1.8151(14)
S1 C2 1.8556(14)
C2 C11 1.5311(18)
C2 C7 1.5587(18)
C2 S3 1.8244(14)
S3 C4 1.8134(14)
C4 C5 1.516(2)
C5 C6 1.517(2)
C7 C8 1.535(2)
C7 C12 1.547(2)
C8 C9 1.522(2)
C9 C10 1.528(2)
C10 C15 1.526(2)
C10 C11 1.531(2)
C12 C14 1.524(2)
C12 C13 1.532(2)
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
O1 S1 C2 C11 49.48(11)
C6 S1 C2 C11 -58.81(10)
O1 S1 C2 C7 -69.39(10)
C6 S1 C2 C7 -177.68(10)
O1 S1 C2 S3 172.64(6)
C6 S1 C2 S3 64.35(8)
C11 C2 S3 C4 53.68(11)
C7 C2 S3 C4 177.81(10)
S1 C2 S3 C4 -67.44(8)
C2 S3 C4 C5 64.70(12)
S3 C4 C5 C6 -60.52(15)
C4 C5 C6 S1 60.31(16)
O1 S1 C6 C5 -172.48(11)
C2 S1 C6 C5 -61.00(12)
C11 C2 C7 C8 55.30(15)
S3 C2 C7 C8 -71.53(13)
S1 C2 C7 C8 175.30(10)
C11 C2 C7 C12 -173.85(12)
S3 C2 C7 C12 59.33(15)
S1 C2 C7 C12 -53.84(15)
C12 C7 C8 C9 170.21(13)
C2 C7 C8 C9 -56.32(16)
C7 C8 C9 C10 56.71(17)
C8 C9 C10 C15 -178.38(13)
C8 C9 C10 C11 -55.16(16)
C7 C2 C11 C10 -57.15(15)
S3 C2 C11 C10 68.14(13)
S1 C2 C11 C10 -174.55(9)
C15 C10 C11 C2 -179.06(12)
C9 C10 C11 C2 56.87(15)
C8 C7 C12 C14 43.32(18)
C2 C7 C12 C14 -86.32(16)
C8 C7 C12 C13 -79.85(16)
C2 C7 C12 C13 150.50(13)