


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015010233/is5399sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015010233/is5399Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015010233/is5399Isup3.cml |
CCDC reference: 1403422
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean
(C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.043
- wR factor = 0.121
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 3.2 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H9C .. O1 .. 2.61 Ang. PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 5 Report PLAT975_ALERT_2_C Check Calcd Residual Density 1.04A From O1 0.44 eA-3
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 4 Note PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00500 Degree PLAT300_ALERT_4_G Atom Site Occupancy of *N1 is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *N1A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C9 is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C9A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C10 is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C10A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C11 is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C11A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C12 is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C12A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H9A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H9B is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H9C is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H9D is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H10A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H10B is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H10C is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H10D is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H11A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H11B is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H11C is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H11D is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H11E is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H11F is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H12A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H12B is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H12C is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H12D is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H12E is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *H12F is Constrained at 0.500 Check PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 31 Note PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 58 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 37 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 33 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Parasitic helminths possess a number of evolutionary strategies that facilitate their co-existence with their host and, as such, up to one third of the global population may suffer from helminthetic infections (de Silva et al., 2003). These parasites can secrete immunomodulatory molecules that prevent the parasites' clearance from the host without leaving the host vulnerable to opportunistic infections (Hewitson et al., 2009). ES-62 is one such immunomodulatory molecule, a protein, which was discovered in the secretions of the rodent filarial nematode Acanthocheilonema and demonstrated to induce an anti-inflammatory immunological phenotype (Harnett et al., 1989). ES-62 has been studied for its potential to treat human diseases relating to inflammation, for example collagen-induced arthritis or rheumatoid arthritis, and many positive outcomes have been demonstrated. A number of the significant anti-inflammatory activities of ES-62 are associated with post-translational glycosylation and subsequent esterification by phosphorylcholine. However, ES-62 is an immunogenic protein and is thus unsuitable as a drug itself (Harnett & Harnett, 2009). We have sought to capitalize on the immunomodulatory effects of ES-62 whilst avoiding its inherent undrugability through synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of ES-62. A series of sulfone analogues (Fig. 1) have proven to be of great significance in our investigations into collagen-induced arthritis. Despite the apparent simplicity of these molecules, we are aware of no relevant crystallographic study. As such, and as the title compound is of particular interest to our ongoing work (Al-Riyami et al., 2013), we report herein on the solid-state structure of the title compound.
The molecular structure of the title compound is shown in Fig. 2. The amine group is disordered over two equally occupied sites such that the lone pair of the pyramidal N atom is anti to O1 with respect to the plane defined by C1—S1—C9 for the conformer containing N1 but syn for the N1A conformer.
Neighbouring molecules related by translation along the a-axis direction are connected by two weak C—H···O hydrogen bonds involving O1 and C1 and C9/C9A (Table 1 and Fig. 3). This gives one-dimensional supramolecular chains of molecules that propagate parallel to the crystallographic a-axis direction.
Other close interactions involve the disordered fragment. Thus the methyl group of C11A approaches the aromatic ring in a π geometry [closest contact C6···C11A = 3.345 (5) Å] whilst C11 forms unfeasibly short intermolecular interactions with its centrosymmetrically related self – an interaction that is relieved by the observed disorder.
A mixture of 2-[(4-methylbenzyl)sulfonyl]ethyl methanesulfonate and 1-methyl-4-[(vinylsulfonyl)methyl]benzene (4.880 g) was dissolved in dichloromethane (50 ml, dry) to which dimethylamine (4 ml, 2M in THF) was added at room temperature with stirring. The stirring was continued at room temperature overnight. The reaction mixture was extracted with a saturated solution of sodium carbonate. The organic layer was collected, dried over MgSO4, filtered and the solvents were removed under reduced pressure and the crude product was applied to a silica gel column chromatography using first ethyl acetate/n-hexane (1/1, RF = 0.1) and then ethyl acetate/methanol (9/1). The product was obtained as a white solid which was recrystallized from ethyl acetate/n-hexane (2.200 g) (m.p. 341–343 K). HRESIMS: calculated for C12H19NO2S, 241.1136; found: 241.1139.
Crystal data, data collection and structure refinement details are summarized in Table 2. Models where the site occupancy factors of the disordered groups were allowed to refine gave occupancies equal to 50%. So in the final model, occupancies of all the disordered atoms were set to this value. The C9—C10 and C9A—C10A distances were restrained to be 1.53 (1) Å. All H atoms were placed in idealized positions and were refined in riding modes with C—H equal to 0.95, 0.98 and 0.99 Å for CH, CH2 and CH3 groups, respectively, and Uiso(H) = 1.5Ueq(C) for methyl groups and 1.2Ueq(C) for other groups.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C12H19NO2S | Z = 2 |
Mr = 241.34 | F(000) = 260 |
Triclinic, P1 | Dx = 1.252 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 5.3642 (3) Å | Cell parameters from 3570 reflections |
b = 10.3773 (6) Å | θ = 5.2–72.9° |
c = 12.1784 (7) Å | µ = 2.14 mm−1 |
α = 99.572 (5)° | T = 123 K |
β = 95.498 (5)° | Plate, colourless |
γ = 104.645 (5)° | 0.30 × 0.10 × 0.03 mm |
V = 639.98 (6) Å3 |
Oxford Diffraction Gemini S diffractometer | 2491 independent reflections |
Radiation source: fine-focus sealed tube | 2360 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 72.9°, θmin = 3.7° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | h = −4→6 |
Tmin = 0.459, Tmax = 0.938 | k = −12→11 |
5846 measured reflections | l = −15→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.2621P] where P = (Fo2 + 2Fc2)/3 |
2491 reflections | (Δ/σ)max < 0.001 |
186 parameters | Δρmax = 0.48 e Å−3 |
2 restraints | Δρmin = −0.35 e Å−3 |
C12H19NO2S | γ = 104.645 (5)° |
Mr = 241.34 | V = 639.98 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.3642 (3) Å | Cu Kα radiation |
b = 10.3773 (6) Å | µ = 2.14 mm−1 |
c = 12.1784 (7) Å | T = 123 K |
α = 99.572 (5)° | 0.30 × 0.10 × 0.03 mm |
β = 95.498 (5)° |
Oxford Diffraction Gemini S diffractometer | 2491 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 2360 reflections with I > 2σ(I) |
Tmin = 0.459, Tmax = 0.938 | Rint = 0.023 |
5846 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 2 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.48 e Å−3 |
2491 reflections | Δρmin = −0.35 e Å−3 |
186 parameters |
Experimental. 1H NMR (DMSO-d6): δ 7.28 (2H, d, J = 8.0 Hz), 7.21 (2H, d, J = 8.0 Hz), 4.44 (2H, s), 3.17 (2H, t, J = 14.3 Hz), 2.65 (2H, t, J = 14.3 Hz), 2.31 (3H, s), 2.16 (6H, s). 13C NMR (DMSO-d6): δ 137.7, 130.8, 129.0, 125.4, 58.4, 51.6, 49.0, 44.9, 20.7. IR (KBr): 1511, 1463, 1399, 1380, 1314, 1258, 1156, 1119, 1050, 892, 853, 822, 749 cm-1. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.89090 (7) | 0.52015 (4) | 0.66118 (3) | 0.02154 (16) | |
O1 | 1.1289 (2) | 0.48170 (12) | 0.68167 (11) | 0.0307 (3) | |
O2 | 0.9042 (2) | 0.63679 (12) | 0.60940 (10) | 0.0295 (3) | |
C1 | 0.6462 (3) | 0.38079 (16) | 0.57471 (13) | 0.0223 (3) | |
H1A | 0.4763 | 0.4021 | 0.5740 | 0.027* | |
H1B | 0.6866 | 0.3706 | 0.4966 | 0.027* | |
C2 | 0.6217 (3) | 0.24813 (16) | 0.61229 (13) | 0.0211 (3) | |
C3 | 0.7832 (3) | 0.16706 (17) | 0.57982 (14) | 0.0252 (4) | |
H3 | 0.9114 | 0.1961 | 0.5338 | 0.030* | |
C4 | 0.7579 (3) | 0.04422 (17) | 0.61421 (14) | 0.0259 (4) | |
H4 | 0.8692 | −0.0101 | 0.5912 | 0.031* | |
C5 | 0.5729 (3) | −0.00109 (17) | 0.68174 (14) | 0.0262 (4) | |
C6 | 0.4119 (4) | 0.08042 (18) | 0.71320 (16) | 0.0300 (4) | |
H6 | 0.2838 | 0.0513 | 0.7592 | 0.036* | |
C7 | 0.4342 (3) | 0.20319 (17) | 0.67902 (14) | 0.0253 (4) | |
H7 | 0.3211 | 0.2568 | 0.7012 | 0.030* | |
C8 | 0.5437 (4) | −0.13542 (19) | 0.71811 (18) | 0.0377 (5) | |
H8A | 0.5787 | −0.1201 | 0.8004 | 0.057* | |
H8B | 0.6676 | −0.1802 | 0.6856 | 0.057* | |
H8C | 0.3659 | −0.1933 | 0.6920 | 0.057* | |
C9 | 0.7696 (3) | 0.55043 (17) | 0.79112 (14) | 0.0248 (4) | 0.50 |
H9A | 0.5883 | 0.5562 | 0.7768 | 0.030* | 0.50 |
H9B | 0.7692 | 0.4741 | 0.8304 | 0.030* | 0.50 |
N1 | 0.8311 (7) | 0.7301 (3) | 0.9652 (3) | 0.0333 (7) | 0.50 |
C10 | 0.9410 (19) | 0.6837 (8) | 0.8655 (9) | 0.0264 (18) | 0.50 |
H10A | 1.1132 | 0.6711 | 0.8900 | 0.032* | 0.50 |
H10B | 0.9689 | 0.7554 | 0.8200 | 0.032* | 0.50 |
C11 | 0.9697 (14) | 0.8715 (5) | 1.0135 (4) | 0.0648 (15) | 0.50 |
H11A | 0.8822 | 0.9060 | 1.0743 | 0.097* | 0.50 |
H11B | 0.9707 | 0.9261 | 0.9551 | 0.097* | 0.50 |
H11C | 1.1492 | 0.8774 | 1.0435 | 0.097* | 0.50 |
C12 | 0.8399 (16) | 0.6456 (6) | 1.0475 (5) | 0.0683 (18) | 0.50 |
H12A | 0.7464 | 0.5512 | 1.0134 | 0.102* | 0.50 |
H12B | 0.7577 | 0.6770 | 1.1114 | 0.102* | 0.50 |
H12C | 1.0216 | 0.6513 | 1.0737 | 0.102* | 0.50 |
N1A | 0.9175 (6) | 0.6553 (3) | 0.9889 (3) | 0.0297 (7) | 0.50 |
C9A | 0.7696 (3) | 0.55043 (17) | 0.79112 (14) | 0.0248 (4) | 0.50 |
H9C | 0.6106 | 0.5813 | 0.7797 | 0.030* | 0.50 |
H9D | 0.7240 | 0.4654 | 0.8207 | 0.030* | 0.50 |
C10A | 0.9780 (18) | 0.6589 (8) | 0.8749 (8) | 0.0231 (17) | 0.50 |
H10C | 1.1504 | 0.6423 | 0.8688 | 0.028* | 0.50 |
H10D | 0.9848 | 0.7496 | 0.8578 | 0.028* | 0.50 |
C11A | 1.1294 (9) | 0.7511 (4) | 1.0688 (3) | 0.0394 (9) | 0.50 |
H11D | 1.2931 | 0.7284 | 1.0582 | 0.059* | 0.50 |
H11E | 1.0940 | 0.7461 | 1.1457 | 0.059* | 0.50 |
H11F | 1.1434 | 0.8434 | 1.0563 | 0.059* | 0.50 |
C12A | 0.6727 (9) | 0.6851 (5) | 1.0055 (4) | 0.0424 (10) | 0.50 |
H12D | 0.6451 | 0.6851 | 1.0839 | 0.064* | 0.50 |
H12E | 0.5301 | 0.6158 | 0.9554 | 0.064* | 0.50 |
H12F | 0.6772 | 0.7746 | 0.9884 | 0.064* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0207 (2) | 0.0219 (2) | 0.0214 (2) | 0.00508 (16) | 0.00401 (15) | 0.00319 (16) |
O1 | 0.0228 (6) | 0.0307 (7) | 0.0357 (7) | 0.0074 (5) | 0.0033 (5) | −0.0006 (5) |
O2 | 0.0357 (7) | 0.0258 (6) | 0.0264 (6) | 0.0050 (5) | 0.0073 (5) | 0.0071 (5) |
C1 | 0.0221 (8) | 0.0237 (8) | 0.0190 (7) | 0.0053 (6) | 0.0001 (6) | 0.0018 (6) |
C2 | 0.0199 (7) | 0.0219 (8) | 0.0182 (7) | 0.0031 (6) | −0.0027 (6) | 0.0016 (6) |
C3 | 0.0220 (8) | 0.0285 (9) | 0.0240 (8) | 0.0066 (7) | 0.0043 (6) | 0.0018 (7) |
C4 | 0.0231 (8) | 0.0255 (8) | 0.0267 (8) | 0.0084 (6) | −0.0005 (6) | −0.0011 (7) |
C5 | 0.0261 (8) | 0.0231 (8) | 0.0258 (8) | 0.0039 (6) | −0.0023 (6) | 0.0031 (6) |
C6 | 0.0275 (9) | 0.0309 (9) | 0.0327 (9) | 0.0060 (7) | 0.0102 (7) | 0.0094 (7) |
C7 | 0.0218 (8) | 0.0274 (8) | 0.0265 (8) | 0.0079 (7) | 0.0041 (6) | 0.0029 (7) |
C8 | 0.0437 (11) | 0.0273 (9) | 0.0433 (11) | 0.0098 (8) | 0.0056 (9) | 0.0110 (8) |
C9 | 0.0252 (8) | 0.0284 (8) | 0.0200 (8) | 0.0062 (7) | 0.0042 (6) | 0.0043 (6) |
N1 | 0.045 (2) | 0.0337 (17) | 0.0244 (16) | 0.0202 (16) | 0.0042 (15) | 0.0002 (13) |
C10 | 0.024 (3) | 0.034 (3) | 0.022 (3) | 0.013 (2) | −0.0005 (19) | 0.001 (2) |
C11 | 0.106 (5) | 0.042 (3) | 0.037 (2) | 0.017 (3) | 0.006 (3) | −0.011 (2) |
C12 | 0.121 (6) | 0.066 (4) | 0.033 (3) | 0.045 (4) | 0.025 (3) | 0.016 (3) |
N1A | 0.0366 (17) | 0.0302 (17) | 0.0197 (17) | 0.0083 (14) | −0.0003 (13) | 0.0013 (13) |
C9A | 0.0252 (8) | 0.0284 (8) | 0.0200 (8) | 0.0062 (7) | 0.0042 (6) | 0.0043 (6) |
C10A | 0.023 (3) | 0.027 (3) | 0.019 (2) | 0.009 (2) | −0.0031 (18) | 0.003 (2) |
C11A | 0.046 (2) | 0.040 (2) | 0.0253 (18) | 0.0098 (18) | −0.0103 (16) | −0.0028 (16) |
C12A | 0.046 (2) | 0.053 (3) | 0.028 (2) | 0.020 (2) | 0.0083 (19) | −0.0024 (18) |
S1—O1 | 1.4426 (13) | C9—H9B | 0.9900 |
S1—O2 | 1.4446 (12) | N1—C12 | 1.442 (6) |
S1—C9 | 1.7780 (16) | N1—C11 | 1.460 (6) |
S1—C1 | 1.7867 (16) | N1—C10 | 1.462 (12) |
C1—C2 | 1.501 (2) | C10—H10A | 0.9900 |
C1—H1A | 0.9900 | C10—H10B | 0.9900 |
C1—H1B | 0.9900 | C11—H11A | 0.9800 |
C2—C7 | 1.391 (2) | C11—H11B | 0.9800 |
C2—C3 | 1.392 (2) | C11—H11C | 0.9800 |
C3—C4 | 1.386 (2) | C12—H12A | 0.9800 |
C3—H3 | 0.9500 | C12—H12B | 0.9800 |
C4—C5 | 1.390 (3) | C12—H12C | 0.9800 |
C4—H4 | 0.9500 | N1A—C12A | 1.448 (6) |
C5—C6 | 1.390 (2) | N1A—C11A | 1.457 (5) |
C5—C8 | 1.507 (2) | N1A—C10A | 1.460 (12) |
C6—C7 | 1.385 (2) | C10A—H10C | 0.9900 |
C6—H6 | 0.9500 | C10A—H10D | 0.9900 |
C7—H7 | 0.9500 | C11A—H11D | 0.9800 |
C8—H8A | 0.9800 | C11A—H11E | 0.9800 |
C8—H8B | 0.9800 | C11A—H11F | 0.9800 |
C8—H8C | 0.9800 | C12A—H12D | 0.9800 |
C9—C10 | 1.536 (7) | C12A—H12E | 0.9800 |
C9—H9A | 0.9900 | C12A—H12F | 0.9800 |
O1—S1—O2 | 117.10 (8) | H8B—C8—H8C | 109.5 |
O1—S1—C9 | 108.51 (8) | C10—C9—S1 | 109.9 (5) |
O2—S1—C9 | 108.29 (8) | C10—C9—H9A | 109.7 |
O1—S1—C1 | 109.89 (7) | S1—C9—H9A | 109.7 |
O2—S1—C1 | 107.22 (7) | C10—C9—H9B | 109.7 |
C9—S1—C1 | 105.17 (8) | S1—C9—H9B | 109.7 |
C2—C1—S1 | 113.98 (11) | H9A—C9—H9B | 108.2 |
C2—C1—H1A | 108.8 | C12—N1—C11 | 110.8 (4) |
S1—C1—H1A | 108.8 | C12—N1—C10 | 111.7 (5) |
C2—C1—H1B | 108.8 | C11—N1—C10 | 109.5 (5) |
S1—C1—H1B | 108.8 | N1—C10—C9 | 113.9 (8) |
H1A—C1—H1B | 107.7 | N1—C10—H10A | 108.8 |
C7—C2—C3 | 118.87 (15) | C9—C10—H10A | 108.8 |
C7—C2—C1 | 120.38 (14) | N1—C10—H10B | 108.8 |
C3—C2—C1 | 120.74 (14) | C9—C10—H10B | 108.8 |
C4—C3—C2 | 120.35 (15) | H10A—C10—H10B | 107.7 |
C4—C3—H3 | 119.8 | C12A—N1A—C11A | 110.2 (3) |
C2—C3—H3 | 119.8 | C12A—N1A—C10A | 112.8 (4) |
C3—C4—C5 | 121.28 (15) | C11A—N1A—C10A | 109.0 (4) |
C3—C4—H4 | 119.4 | N1A—C10A—H10C | 109.8 |
C5—C4—H4 | 119.4 | N1A—C10A—H10D | 109.8 |
C4—C5—C6 | 117.86 (16) | H10C—C10A—H10D | 108.2 |
C4—C5—C8 | 121.24 (16) | N1A—C11A—H11D | 109.5 |
C6—C5—C8 | 120.90 (16) | N1A—C11A—H11E | 109.5 |
C7—C6—C5 | 121.50 (16) | H11D—C11A—H11E | 109.5 |
C7—C6—H6 | 119.3 | N1A—C11A—H11F | 109.5 |
C5—C6—H6 | 119.3 | H11D—C11A—H11F | 109.5 |
C6—C7—C2 | 120.15 (15) | H11E—C11A—H11F | 109.5 |
C6—C7—H7 | 119.9 | N1A—C12A—H12D | 109.5 |
C2—C7—H7 | 119.9 | N1A—C12A—H12E | 109.5 |
C5—C8—H8A | 109.5 | H12D—C12A—H12E | 109.5 |
C5—C8—H8B | 109.5 | N1A—C12A—H12F | 109.5 |
H8A—C8—H8B | 109.5 | H12D—C12A—H12F | 109.5 |
C5—C8—H8C | 109.5 | H12E—C12A—H12F | 109.5 |
H8A—C8—H8C | 109.5 | ||
O1—S1—C1—C2 | 47.30 (14) | C8—C5—C6—C7 | −179.06 (16) |
O2—S1—C1—C2 | 175.57 (11) | C5—C6—C7—C2 | −0.4 (3) |
C9—S1—C1—C2 | −69.31 (13) | C3—C2—C7—C6 | 0.7 (2) |
S1—C1—C2—C7 | 96.45 (16) | C1—C2—C7—C6 | 179.81 (14) |
S1—C1—C2—C3 | −84.47 (17) | O1—S1—C9—C10 | 72.2 (3) |
C7—C2—C3—C4 | −0.4 (2) | O2—S1—C9—C10 | −55.9 (3) |
C1—C2—C3—C4 | −179.51 (14) | C1—S1—C9—C10 | −170.2 (3) |
C2—C3—C4—C5 | −0.2 (3) | C12—N1—C10—C9 | 71.5 (7) |
C3—C4—C5—C6 | 0.5 (3) | C11—N1—C10—C9 | −165.3 (5) |
C3—C4—C5—C8 | 179.36 (16) | S1—C9—C10—N1 | 169.5 (4) |
C4—C5—C6—C7 | −0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.99 | 2.60 | 3.493 (2) | 150 |
C9—H9A···O1i | 0.99 | 2.49 | 3.415 (2) | 155 |
C9A—H9C···O1i | 0.99 | 2.61 | 3.415 (2) | 138 |
Symmetry code: (i) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.99 | 2.60 | 3.493 (2) | 150 |
C9—H9A···O1i | 0.99 | 2.49 | 3.415 (2) | 155 |
C9A—H9C···O1i | 0.99 | 2.61 | 3.415 (2) | 138 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C12H19NO2S |
Mr | 241.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 123 |
a, b, c (Å) | 5.3642 (3), 10.3773 (6), 12.1784 (7) |
α, β, γ (°) | 99.572 (5), 95.498 (5), 104.645 (5) |
V (Å3) | 639.98 (6) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 2.14 |
Crystal size (mm) | 0.30 × 0.10 × 0.03 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini S diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.459, 0.938 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5846, 2491, 2360 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.620 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.121, 1.08 |
No. of reflections | 2491 |
No. of parameters | 186 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.35 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008).