Crystal structure of N,N-dimethyl-2-[(4-methyl­benz­yl)sulfon­yl]ethanamine

The title compound has a disordered structure with two equally populated conformations of the amine fragment. A pair of weak C—H...O inter­molecular inter­actions between the CH₂ and SO₂ groups gives a one-dimensional supra­molecular structure running along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](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

---

S1. Chemical context

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.

S2. Structural commentary

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.

S3. Supra­molecular features

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.

S4. Synthesis and crystallization

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.

S5. Refinement

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 U_iso(H) = 1.5U_eq(C) for methyl groups and 1.2U_eq(C) for other groups.

Related literature

For the immunomodulatory role of ES-62, see: de Silva et al. (2003); Harnett et al. (1989); Harnett & Harnett (2009); Hewitson et al. (2009). For sulfones and collagen-induced arthritis, see: Al-Riyami et al. (2013)

Computing details

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).

Figures

	Fig. 1. General structure of sulfone analogues. R represents alkyl chains and X represents halogen substituents.
	Fig. 2. The molecular structure of the title compound with non-H atoms shown as 50% probability ellipsoids. For the disordered fragment, the atoms labelled with the suffix `a' have been shown with hollow bonds whilst all other bonds are shown as solid lines.
	Fig. 3. Part of the molecular chain formed by translation along a highlighting the C—H···O contacts. Only one of the two disordered conformations is shown.

N,N-Dimethyl-2-[(4-methylbenzyl)sulfonyl]ethanamine

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 0.2621P] where P = (Fo^2 + 2Fc^2)/3
2491 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.48 e Å^−3
2 restraints	Δρmin = −0.35 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1^i	0.99	2.60	3.493 (2)	150
C9—H9A···O1^i	0.99	2.49	3.415 (2)	155
C9A—H9C···O1^i	0.99	2.61	3.415 (2)	138

Symmetry code: (i) x−1, y, z.