10-Methyl- and 9,10-dimethyl­acridinium methyl sulfate

The title compounds, C₁₄H₁₂N⁺·CH₃O₄S⁻, (I), and C₁₅H₁₄N⁺·CH₃O₄S⁻, (II), respectively, crystallize with the planar 10-methylacridinium or 9,10-di­methyl­acridinium cations arranged in layers, parallel to the twofold axis in (I) and perpendicular to the 2₁ axis in (II). Adjacent cations in both compounds are packed in a `head-to-tail' manner. The methyl sulfate anion only exhibits planar symmetry in (II). The cations and anions are linked through C—H...O interactions involving three O atoms of the anion, six acridine H atoms and the CH₃ group on the N atom in (I), and the four O atoms of the anion, three acridine H atoms and the carbon-bound CH₃ group in (II). The methyl sulfate anions are oriented differently in the two compounds relative to the cations, being nearly perpendicular in (I) but parallel in (II). Electrostatic interaction between the ions and the network of C—H...O interactions leads to relatively compact crystal lattices in both structures.

S1. Comment

Methylation of acridines is the simplest way of converting them to stable cationic forms (Storoniak et al., 2000), which are fairly readily soluble in water. Unlike their protonated forms, methylated acridines are resistant to changes in pH, and are thus convenient derivatives for numerous applications. In undertaking these investigations, we also wished to consider the susceptibility to oxidation of acridinium cations methylated at the N atom. This process requires the presence of oxidizing agents (e.g. peroxides) and may be accompanied by chemiluminescence (Dodeigne et al., 2000). In this context, we recently investigated 9-carboxy-10-methylacridinium phenyl ester (Rak et al., 1999) and 9-cyano-10-methylacridinium hydrogen dinitrate (Huta et al., 2002), and determined the structure of the latter.

It is also interesting that the 9,10-dimethylacridinium cation is one of the strongest C-acids Please clarify, and can therefore serve as a model for investigating this feature of organic compounds (Suzuki & Tanaka, 2001). The present work is a continuation of our search for 10-methylacridinium derivatives capable of undergoing oxidation leading to the formation of electronically excited 9-acridinones. Both compounds under study here, 10-methylacridinium methyl sulfate, (I), and 9,10-dimethylacridinium methyl sulfate, (II), contain the simplest possible 10-methylacridinium cations. They can be regarded as convenient models for the study of the susceptibility to oxidation of this group of compounds. \sch

The methyl sulfate anion in (I) does not exhibit plane symmetry, unlike in (II), as demonstrated by the O2—S1—O1—C16 angle (Table 1). Atoms C9 and N10, as well as the methyl group in the cation, are arranged almost linearly [C9···N10—C15 178.0 (2)°]. The methyl group in the cation is fixed in a certain position, as in 10-methylacridinium halides (Storoniak et al., 2000). The methyl group of the anion is similarly fixed; this is not the case in (II).

In (I), the anions are arranged almost perpendicular to the nearly planar acridine moieties [the angle between the O1/S1/O2 plane and the ac plane is 85.7 (1)°], which form layers parallel to the b axis [the angle between the mean plane formed by the non-H atoms of the cation and the ac plane is 89.8 (1)°]. The cations and anions are fixed, as a result of multidirectional C—H···O interactions involving three O atoms of the anion and the six H atoms attached to the acridine C atoms in ring positions 1–5 and 9, as well as those belonging to the methyl group at N10 (Table 2).

The methyl sulfate anion in (II) lies in the crystallographic symmetry plane. As a consequence, the H atoms of the methyl group occupy two orientations, rotated by 60°, each with an occupancy of 0.5 (Table 3). Atoms C9 and N10, together with the methyl groups attached to them, are arranged linearly [C15—C9···N10—C16 179.5 (2)°]. However, the H atoms of both methyl groups occupy two orientations, twisted through 39 and 60° for CH₃ attached to atoms C9 and N10, respectively, each with an occupancy of 0.5.

In the crystal of (II), the cations and anions are arranged in layers perpendicular to the 2₁ axis (parallel to the ac plane; Fig. 4), with adjacent ions arranged `head-to-tail'. These layers are linked through C—H···O interactions involving all four O atoms of the anion and the three H atoms attached to the acridine C atoms at ring positions 1, 2 and 4, and those belonging to the carbon-bound methyl group at C9 (Table 4). The cations and anions form columns along the [010] direction and are held in place by the network of these multidirectional interactions.

The methyl group at N10 in (II) occupies two orientations, as in 9-cyano-10-methylacridinium hydrogen dinitrate (Huta et al., 2002), while in (I) it is fixed, as in the 10-methylacridinium halides (Storoniak et al., 2000). It is also of interest to note that the methyl sulfate anion in (II) is symmetrical. This is a unique feature among those salts containing this anion for which crystal structures have so far been established (Blake et al., 2000; Brand & Vahrenkamp, 2000; Handrosch et al., 1999; Senge & Kalisch, 1999); none of these contains symmetrical methyl sulfate anions. It is perhaps also worth mentioning that (II) is the first ionic substance containing the 9,10-dimethylacridinium cation for which the structure has been determined by X-ray methods. Therefore, 9,10-dimethylacridinium methyl sulfate appears to be a crystalline substance combining the symmetries of both cation and anion.

S2. Experimental

Commercially available acridine was purified by sublimation (Storoniak et al., 2000). 9-Methylacridine was synthesized following the procedure described by Tsuge et al. (1963). 10-Methylacridinium and 9,10-dimethylacridinium methyl sulfates were prepared by the reaction of acridine and 9-methylacridine, respectively, with dimethyl sulfuric acid (Bahr et al., 1996; Mooser et al., 1972). Yellow crystals of (I) and red crystals of (II), suitable for X-ray analyses, were grown from solutions in 96% alcohol. Which alcohol?

S3. Refinement

All H atoms were placed geometrically and refined using a riding model, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) in the case of methyl H atoms, and C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for all others.

Computing details

For both compounds, data collection: KM-4 Software (Kuma Diffraction, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and with 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The arrangement of molecules of (I) in the unit cell, viewed along the b axis. Short C—H···O contacts are represented by dashed lines.
	Fig. 3. The molecular structure of (II), showing the atom-labelling scheme and with 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii [symmetry code: (i) x, 1/2 - y, z].
	Fig. 4. A stereoview of the packing diagram of (II), viewed along the b axis, with the a axis vertical and the c axis horizontal. Short C—H···O contacts (Table 4) are represented by dashed lines.

(I) 10-methylacridinium methyl sulfate

Crystal data

C14H12N^+·CH3O4S^−	F(000) = 1280
Mr = 305.34	Dx = 1.479 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 50 reflections
a = 16.199 (5) Å	θ = 6.0–24.0°
b = 12.661 (4) Å	µ = 2.25 mm^−1
c = 14.785 (4) Å	T = 293 K
β = 115.23 (3)°	Prism, yellow
V = 2743.1 (16) Å^3	0.4 × 0.3 × 0.3 mm
Z = 8

Data collection

Kuma KM-4 diffractometer	Rint = 0.066
Radiation source: fine-focus sealed tube	θmax = 72.0°, θmin = 4.6°
Graphite monochromator	h = −18→18
θ/2θ scans	k = 0→15
2774 measured reflections	l = 0→17
2663 independent reflections	3 standard reflections every 200 reflections
2150 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1082P)^2 + 1.7878P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
2663 reflections	Δρmax = 0.31 e Å^−3
193 parameters	Δρmin = −0.54 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
S1	0.26367 (4)	0.46170 (5)	0.10441 (4)	0.0419 (3)
O1	0.32483 (14)	0.44867 (16)	0.04407 (15)	0.0540 (5)
O2	0.23487 (15)	0.56980 (16)	0.08212 (17)	0.0631 (6)
O3	0.32312 (16)	0.44171 (18)	0.20691 (15)	0.0604 (6)
O4	0.19128 (15)	0.38575 (18)	0.06352 (18)	0.0667 (6)
C1	−0.06295 (19)	0.2587 (2)	0.0532 (2)	0.0533 (7)
H1A	−0.1163	0.2811	0.0002	0.064*
C2	−0.0459 (2)	0.1544 (3)	0.0698 (2)	0.0634 (8)
H2A	−0.0875	0.1051	0.0287	0.076*
C3	0.0355 (2)	0.1207 (2)	0.1498 (2)	0.0628 (8)
H3A	0.0468	0.0487	0.1603	0.075*
C4	0.0979 (2)	0.1902 (2)	0.2120 (2)	0.0540 (7)
H4A	0.1511	0.1656	0.2640	0.065*
C5	0.1889 (2)	0.5553 (2)	0.3026 (2)	0.0529 (7)
H5A	0.2421	0.5336	0.3563	0.063*
C6	0.1715 (2)	0.6606 (3)	0.2830 (2)	0.0594 (7)
H6A	0.2138	0.7098	0.3233	0.071*
C7	0.0914 (2)	0.6962 (2)	0.2038 (2)	0.0590 (7)
H7A	0.0809	0.7682	0.1925	0.071*
C8	0.02934 (19)	0.6259 (2)	0.1437 (2)	0.0510 (6)
H8A	−0.0238	0.6497	0.0912	0.061*
C9	−0.01673 (17)	0.4416 (2)	0.09988 (19)	0.0460 (6)
H9A	−0.0704	0.4641	0.0474	0.055*
N10	0.14120 (14)	0.37353 (18)	0.25871 (15)	0.0425 (5)
C11	0.00023 (16)	0.3344 (2)	0.11630 (18)	0.0436 (6)
C12	0.08175 (17)	0.2998 (2)	0.19731 (19)	0.0437 (6)
C13	0.04510 (17)	0.5160 (2)	0.16049 (19)	0.0435 (6)
C14	0.12617 (17)	0.4800 (2)	0.24143 (18)	0.0432 (6)
C15	0.22459 (18)	0.3402 (3)	0.3454 (2)	0.0562 (7)
H15C	0.2247	0.2647	0.3519	0.084*
H15B	0.2263	0.3724	0.4050	0.084*
H15A	0.2772	0.3617	0.3360	0.084*
C16	0.3738 (3)	0.3523 (3)	0.0578 (3)	0.0715 (9)
H16C	0.4022	0.3498	0.0126	0.107*
H16B	0.3326	0.2939	0.0447	0.107*
H16A	0.4199	0.3483	0.1254	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0422 (4)	0.0391 (4)	0.0412 (4)	0.0013 (2)	0.0148 (3)	−0.0004 (2)
O1	0.0587 (11)	0.0552 (11)	0.0548 (11)	0.0041 (9)	0.0306 (9)	0.0081 (8)
O2	0.0663 (13)	0.0453 (11)	0.0642 (13)	0.0156 (10)	0.0149 (10)	0.0042 (9)
O3	0.0683 (13)	0.0644 (12)	0.0404 (10)	0.0121 (10)	0.0154 (9)	0.0042 (8)
O4	0.0545 (11)	0.0606 (13)	0.0827 (16)	−0.0168 (10)	0.0271 (11)	−0.0124 (10)
C1	0.0421 (13)	0.0609 (16)	0.0493 (15)	−0.0065 (12)	0.0122 (11)	0.0056 (12)
C2	0.0562 (17)	0.0614 (18)	0.0625 (18)	−0.0132 (14)	0.0157 (14)	0.0033 (14)
C3	0.0642 (18)	0.0508 (16)	0.0670 (19)	−0.0051 (13)	0.0217 (15)	0.0112 (13)
C4	0.0486 (14)	0.0582 (16)	0.0503 (15)	0.0030 (12)	0.0163 (12)	0.0139 (12)
C5	0.0481 (14)	0.0605 (16)	0.0456 (14)	0.0007 (12)	0.0156 (11)	−0.0082 (12)
C6	0.0549 (16)	0.0655 (19)	0.0582 (17)	−0.0071 (14)	0.0247 (14)	−0.0189 (14)
C7	0.0636 (18)	0.0540 (16)	0.0629 (18)	0.0062 (13)	0.0302 (15)	−0.0072 (13)
C8	0.0499 (14)	0.0539 (15)	0.0494 (14)	0.0140 (12)	0.0214 (12)	0.0048 (11)
C9	0.0361 (12)	0.0611 (15)	0.0383 (12)	0.0070 (10)	0.0134 (10)	0.0069 (11)
N10	0.0345 (10)	0.0553 (12)	0.0351 (10)	0.0042 (8)	0.0124 (8)	0.0052 (8)
C11	0.0374 (12)	0.0571 (15)	0.0363 (12)	−0.0006 (10)	0.0157 (10)	0.0045 (10)
C12	0.0380 (12)	0.0562 (15)	0.0379 (12)	0.0002 (10)	0.0172 (10)	0.0072 (10)
C13	0.0396 (12)	0.0542 (15)	0.0385 (12)	0.0081 (10)	0.0184 (10)	0.0018 (10)
C14	0.0382 (12)	0.0560 (15)	0.0366 (12)	0.0051 (10)	0.0171 (10)	0.0001 (10)
C15	0.0416 (13)	0.0682 (18)	0.0441 (15)	0.0043 (12)	0.0041 (11)	0.0060 (12)
C16	0.079 (2)	0.0645 (19)	0.087 (2)	0.0199 (17)	0.050 (2)	0.0069 (17)

Geometric parameters (Å, º)

S1—O1	1.599 (2)	C7—C8	1.354 (4)
S1—O2	1.438 (2)	C7—H7A	0.9300
S1—O3	1.430 (2)	C8—C13	1.417 (4)
S1—O4	1.436 (2)	C8—H8A	0.9300
O1—C16	1.422 (4)	C9—C11	1.385 (4)
C1—C2	1.350 (4)	C9—C13	1.389 (4)
C1—C11	1.422 (4)	C9—H9A	0.9300
C1—H1A	0.9300	N10—C12	1.370 (3)
C2—C3	1.411 (4)	N10—C14	1.375 (3)
C2—H2A	0.9300	N10—C15	1.473 (3)
C3—C4	1.360 (4)	C11—C12	1.422 (3)
C3—H3A	0.9300	C13—C14	1.423 (3)
C4—C12	1.412 (4)	C15—H15C	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.368 (4)	C15—H15A	0.9600
C5—C14	1.406 (4)	C16—H16C	0.9600
C5—H5A	0.9300	C16—H16B	0.9600
C6—C7	1.400 (4)	C16—H16A	0.9600
C6—H6A	0.9300
O3—S1—O4	112.83 (15)	C11—C9—C13	121.1 (2)
O3—S1—O2	114.68 (13)	C11—C9—H9A	119.4
O4—S1—O2	114.46 (14)	C13—C9—H9A	119.4
O3—S1—O1	105.99 (13)	C12—N10—C14	121.7 (2)
O4—S1—O1	106.56 (12)	C12—N10—C15	120.4 (2)
O2—S1—O1	100.83 (12)	C14—N10—C15	117.8 (2)
C16—O1—S1	116.73 (18)	C9—C11—C12	119.5 (2)
C2—C1—C11	120.4 (3)	C9—C11—C1	120.8 (2)
C2—C1—H1A	119.8	C12—C11—C1	119.7 (3)
C11—C1—H1A	119.8	N10—C12—C4	122.4 (2)
C1—C2—C3	119.6 (3)	N10—C12—C11	119.1 (2)
C1—C2—H2A	120.2	C4—C12—C11	118.5 (2)
C3—C2—H2A	120.2	C9—C13—C8	121.7 (2)
C4—C3—C2	122.0 (3)	C9—C13—C14	118.6 (2)
C4—C3—H3A	119.0	C8—C13—C14	119.6 (3)
C2—C3—H3A	119.0	N10—C14—C5	121.6 (2)
C3—C4—C12	119.8 (3)	N10—C14—C13	119.8 (2)
C3—C4—H4A	120.1	C5—C14—C13	118.6 (3)
C12—C4—H4A	120.1	N10—C15—H15C	109.5
C6—C5—C14	119.8 (3)	N10—C15—H15B	109.5
C6—C5—H5A	120.1	H15C—C15—H15B	109.5
C14—C5—H5A	120.1	N10—C15—H15A	109.5
C5—C6—C7	121.6 (3)	H15C—C15—H15A	109.5
C5—C6—H6A	119.2	H15B—C15—H15A	109.5
C7—C6—H6A	119.2	O1—C16—H16C	109.5
C8—C7—C6	120.1 (3)	O1—C16—H16B	109.5
C8—C7—H7A	119.9	H16C—C16—H16B	109.5
C6—C7—H7A	119.9	O1—C16—H16A	109.5
C7—C8—C13	120.2 (3)	H16C—C16—H16A	109.5
C7—C8—H8A	119.9	H16B—C16—H16A	109.5
C13—C8—H8A	119.9
O3—S1—O1—C16	53.6 (3)	C9—C11—C12—N10	1.2 (4)
O4—S1—O1—C16	−66.9 (3)	C1—C11—C12—N10	−178.7 (2)
O2—S1—O1—C16	173.4 (2)	C9—C11—C12—C4	−179.4 (2)
C11—C1—C2—C3	−0.5 (5)	C1—C11—C12—C4	0.7 (4)
C1—C2—C3—C4	0.4 (5)	C11—C9—C13—C8	179.0 (2)
C2—C3—C4—C12	0.2 (5)	C11—C9—C13—C14	−1.0 (4)
C14—C5—C6—C7	1.0 (5)	C7—C8—C13—C9	−179.5 (3)
C5—C6—C7—C8	−0.7 (5)	C7—C8—C13—C14	0.5 (4)
C6—C7—C8—C13	−0.1 (4)	C12—N10—C14—C5	−177.8 (2)
C13—C9—C11—C12	0.8 (4)	C15—N10—C14—C5	1.4 (4)
C13—C9—C11—C1	−179.3 (2)	C12—N10—C14—C13	2.8 (4)
C2—C1—C11—C9	−180.0 (3)	C15—N10—C14—C13	−177.9 (2)
C2—C1—C11—C12	0.0 (4)	C6—C5—C14—N10	−180.0 (3)
C14—N10—C12—C4	177.6 (2)	C6—C5—C14—C13	−0.6 (4)
C15—N10—C12—C4	−1.6 (4)	C9—C13—C14—N10	−0.7 (4)
C14—N10—C12—C11	−3.0 (3)	C8—C13—C14—N10	179.2 (2)
C15—N10—C12—C11	177.8 (2)	C9—C13—C14—C5	179.8 (2)
C3—C4—C12—N10	178.6 (3)	C8—C13—C14—C5	−0.2 (4)
C3—C4—C12—C11	−0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2^i	0.93	2.60	3.424 (4)	149
C2—H2A···O1^ii	0.93	2.50	3.261 (4)	139
C3—H3A···O3^iii	0.93	2.57	3.276 (4)	133
C4—H4A···O2^iii	0.93	2.54	3.449 (4)	164
C5—H5A···O1^iv	0.93	2.52	3.300 (4)	141
C9—H9A···O2^i	0.93	2.57	3.412 (4)	151
C15—H15A···O3	0.96	2.53	3.344 (4)	141

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1/2, y−1/2, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x, −y+1, z+1/2.

(II) 9,10-dimethylacridinium methyl sulfate

Crystal data

C15H14N^+·CH3O4S^−	F(000) = 336
Mr = 319.37	Dx = 1.455 Mg m^−3
Monoclinic, P21/m	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yb	Cell parameters from 50 reflections
a = 9.271 (2) Å	θ = 6–24°
b = 6.822 (1) Å	µ = 2.14 mm^−1
c = 11.591 (2) Å	T = 293 K
β = 96.24 (3)°	Prism, red
V = 728.7 (2) Å^3	0.40 × 0.40 × 0.35 mm
Z = 2

Data collection

Kuma KM-4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 72.0°, θmin = 3.8°
Graphite monochromator	h = −8→11
θ/2θ scans	k = −8→0
1620 measured reflections	l = −14→8
1565 independent reflections	3 standard reflections every 200 reflections
1454 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0839P)^2 + 0.1827P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1565 reflections	Δρmax = 0.35 e Å^−3
131 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.070 (5)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	−0.02870 (6)	0.2500	0.22575 (5)	0.0485 (3)
O1	0.1206 (2)	0.2500	0.17339 (18)	0.0771 (8)
O2	0.0158 (2)	0.2500	0.34805 (17)	0.0721 (7)
O3	−0.1032 (2)	0.4224 (3)	0.18400 (14)	0.0893 (6)
C1	0.3754 (3)	0.2500	0.4159 (2)	0.0460 (6)
H1A	0.2746	0.2500	0.4116	0.055*
C2	0.4405 (3)	0.2500	0.3169 (2)	0.0528 (6)
H2A	0.3842	0.2500	0.2454	0.063*
C3	0.5922 (3)	0.2500	0.3213 (2)	0.0561 (7)
H3A	0.6357	0.2500	0.2526	0.067*
C4	0.6762 (3)	0.2500	0.4246 (2)	0.0502 (6)
H4A	0.7767	0.2500	0.4259	0.060*
C5	0.4203 (4)	0.2500	0.8427 (3)	0.0689 (9)
H5A	0.3201	0.2500	0.8430	0.083*
C6	0.5064 (5)	0.2500	0.9443 (3)	0.0868 (12)
H6A	0.4648	0.2500	1.0137	0.104*
C7	0.6571 (5)	0.2500	0.9464 (3)	0.0900 (13)
H7A	0.7147	0.2500	1.0173	0.108*
C8	0.7207 (4)	0.2500	0.8463 (3)	0.0695 (9)
H8A	0.8214	0.2500	0.8493	0.083*
C9	0.3929 (2)	0.2500	0.6296 (2)	0.0389 (5)
N10	0.6974 (2)	0.2500	0.6354 (2)	0.0471 (5)
C11	0.4584 (2)	0.2500	0.5263 (2)	0.0391 (5)
C12	0.6132 (2)	0.2500	0.5307 (2)	0.0402 (5)
C13	0.4807 (3)	0.2500	0.7354 (2)	0.0469 (6)
C14	0.6353 (3)	0.2500	0.7379 (2)	0.0474 (6)
C15	0.2306 (3)	0.2500	0.6277 (2)	0.0535 (7)
H15A	0.2030	0.1636	0.6868	0.080*	0.50
H15B	0.1977	0.3804	0.6417	0.080*	0.50
H15C	0.1874	0.2060	0.5531	0.080*	0.50
C16	0.8588 (3)	0.2500	0.6377 (3)	0.0658 (8)
H16A	0.8858	0.3203	0.5716	0.099*	0.50
H16B	0.9012	0.3123	0.7075	0.099*	0.50
H16C	0.8930	0.1174	0.6355	0.099*	0.50
C17	0.1151 (4)	0.2500	0.0489 (3)	0.0790 (11)
H17A	0.0293	0.1829	0.0162	0.118*	0.50
H17B	0.1993	0.1845	0.0263	0.118*	0.50
H17C	0.1133	0.3827	0.0212	0.118*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0356 (4)	0.0726 (5)	0.0375 (4)	0.000	0.0052 (2)	0.000
O1	0.0404 (10)	0.144 (2)	0.0476 (11)	0.000	0.0105 (8)	0.000
O2	0.0527 (11)	0.125 (2)	0.0385 (10)	0.000	0.0040 (8)	0.000
O3	0.1036 (13)	0.1001 (14)	0.0641 (9)	0.0445 (12)	0.0082 (9)	0.0005 (9)
C1	0.0364 (11)	0.0523 (13)	0.0487 (13)	0.000	0.0012 (10)	0.000
C2	0.0519 (14)	0.0625 (16)	0.0430 (13)	0.000	0.0014 (11)	0.000
C3	0.0530 (14)	0.0677 (17)	0.0502 (14)	0.000	0.0175 (11)	0.000
C4	0.0366 (12)	0.0576 (15)	0.0589 (15)	0.000	0.0160 (11)	0.000
C5	0.0612 (17)	0.100 (3)	0.0469 (15)	0.000	0.0130 (13)	0.000
C6	0.083 (2)	0.132 (4)	0.0453 (16)	0.000	0.0083 (15)	0.000
C7	0.084 (2)	0.134 (4)	0.0472 (17)	0.000	−0.0138 (16)	0.000
C8	0.0528 (16)	0.095 (2)	0.0573 (17)	0.000	−0.0101 (13)	0.000
C9	0.0323 (11)	0.0421 (11)	0.0428 (12)	0.000	0.0067 (9)	0.000
N10	0.0336 (10)	0.0504 (11)	0.0566 (13)	0.000	0.0015 (8)	0.000
C11	0.0313 (11)	0.0410 (11)	0.0452 (12)	0.000	0.0053 (9)	0.000
C12	0.0322 (11)	0.0400 (11)	0.0484 (13)	0.000	0.0047 (9)	0.000
C13	0.0422 (13)	0.0535 (14)	0.0451 (13)	0.000	0.0052 (10)	0.000
C14	0.0422 (13)	0.0506 (13)	0.0482 (13)	0.000	−0.0007 (10)	0.000
C15	0.0340 (12)	0.0710 (17)	0.0567 (15)	0.000	0.0107 (10)	0.000
C16	0.0319 (12)	0.092 (2)	0.0716 (19)	0.000	−0.0024 (12)	0.000
C17	0.0658 (19)	0.124 (3)	0.0503 (16)	0.000	0.0219 (14)	0.000

Geometric parameters (Å, º)

S1—O1	1.571 (2)	C8—C14	1.412 (4)
S1—O2	1.433 (2)	C8—H8A	0.9300
S1—O3	1.4221 (18)	C9—C13	1.396 (3)
O1—C17	1.438 (4)	C9—C11	1.401 (3)
C1—C2	1.354 (4)	C9—C15	1.502 (3)
C1—C11	1.419 (3)	N10—C12	1.370 (3)
C1—H1A	0.9300	N10—C14	1.376 (4)
C2—C3	1.402 (4)	N10—C16	1.493 (3)
C2—H2A	0.9300	C11—C12	1.430 (3)
C3—C4	1.356 (4)	C13—C14	1.430 (3)
C3—H3A	0.9300	C15—H15A	0.9600
C4—C12	1.417 (4)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.349 (5)	C16—H16A	0.9600
C5—C13	1.418 (4)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.395 (6)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.357 (5)	C17—H17C	0.9600
C7—H7A	0.9300
O1—S1—O2	102.19 (11)	C12—N10—C16	119.3 (2)
O1—S1—O3	106.54 (10)	C14—N10—C16	119.8 (2)
O2—S1—O3	114.44 (8)	C9—C11—C1	121.8 (2)
C17—O1—S1	116.82 (19)	C9—C11—C12	119.7 (2)
C2—C1—C11	121.0 (2)	C1—C11—C12	118.5 (2)
C2—C1—H1A	119.5	N10—C12—C4	121.3 (2)
C11—C1—H1A	119.5	N10—C12—C11	120.4 (2)
C1—C2—C3	120.5 (2)	C4—C12—C11	118.4 (2)
C1—C2—H2A	119.8	C9—C13—C5	121.5 (3)
C3—C2—H2A	119.8	C9—C13—C14	120.3 (2)
C4—C3—C2	120.6 (3)	C5—C13—C14	118.2 (3)
C4—C3—H3A	119.7	N10—C14—C8	121.4 (2)
C2—C3—H3A	119.7	N10—C14—C13	119.7 (2)
C3—C4—C12	121.0 (2)	C8—C14—C13	118.8 (3)
C3—C4—H4A	119.5	C9—C15—H15A	109.5
C12—C4—H4A	119.5	C9—C15—H15B	109.5
C6—C5—C13	120.9 (3)	H15A—C15—H15B	109.5
C6—C5—H5A	119.6	C9—C15—H15C	109.5
C13—C5—H5A	119.6	H15A—C15—H15C	109.5
C5—C6—C7	120.8 (3)	H15B—C15—H15C	109.5
C5—C6—H6A	119.6	N10—C16—H16A	109.5
C7—C6—H6A	119.6	N10—C16—H16B	109.5
C8—C7—C6	120.8 (3)	H16A—C16—H16B	109.5
C8—C7—H7A	119.6	N10—C16—H16C	109.5
C6—C7—H7A	119.6	H16A—C16—H16C	109.5
C7—C8—C14	120.5 (3)	H16B—C16—H16C	109.5
C7—C8—H8A	119.8	O1—C17—H17A	109.5
C14—C8—H8A	119.8	O1—C17—H17B	109.5
C13—C9—C11	119.0 (2)	H17A—C17—H17B	109.5
C13—C9—C15	120.0 (2)	O1—C17—H17C	109.5
C11—C9—C15	120.9 (2)	H17A—C17—H17C	109.5
C12—N10—C14	120.8 (2)	H17B—C17—H17C	109.5
O3—S1—O1—C17	−59.62 (8)	C9—C11—C12—C4	180.0
O2—S1—O1—C17	180.0	C1—C11—C12—C4	0.0
C11—C1—C2—C3	0.0	C11—C9—C13—C5	180.0
C1—C2—C3—C4	0.0	C15—C9—C13—C5	0.0
C2—C3—C4—C12	0.0	C11—C9—C13—C14	0.0
C13—C5—C6—C7	0.0	C15—C9—C13—C14	180.0
C5—C6—C7—C8	0.0	C6—C5—C13—C9	180.0
C6—C7—C8—C14	0.0	C6—C5—C13—C14	0.0
C13—C9—C11—C1	180.0	C12—N10—C14—C8	180.0
C15—C9—C11—C1	0.0	C16—N10—C14—C8	0.0
C13—C9—C11—C12	0.0	C12—N10—C14—C13	0.0
C15—C9—C11—C12	180.0	C16—N10—C14—C13	180.0
C2—C1—C11—C9	180.0	C7—C8—C14—N10	180.0
C2—C1—C11—C12	0.0	C7—C8—C14—C13	0.0
C14—N10—C12—C4	180.0	C9—C13—C14—N10	0.0
C16—N10—C12—C4	0.0	C5—C13—C14—N10	180.0
C14—N10—C12—C11	0.0	C9—C13—C14—C8	180.0
C16—N10—C12—C11	180.0	C5—C13—C14—C8	0.0
C3—C4—C12—N10	180.0	S1—O1—C17—H17A	−30.4
C3—C4—C12—C11	0.0	C11—C9—C15—H15A	139.4
C9—C11—C12—N10	0.0	C12—N10—C16—H16A	32.0
C1—C11—C12—N10	180.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2	0.93	2.43	3.341 (3)	166
C2—H2A···O1	0.93	2.49	3.239 (4)	137
C4—H4A···O2^i	0.93	2.48	3.363 (4)	158
C15—H15A···O3^ii	0.96	2.47	3.423 (3)	171
C15—H15A^iii···O3^iv	0.96	2.47	3.423 (3)	171

Symmetry codes: (i) x+1, y, z; (ii) −x, y−1/2, −z+1; (iii) x, −y+1/2, z; (iv) −x, −y+1, −z+1.