9-(2-Acetoxy­ethoxy­meth­yl)-2-formamido-6-(p-tolyl­sulfon­yloxy)purine

Belyakov, S.; Ikaunieks, M.; Madre, M.

doi:10.1107/S1600536805030175

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9-(2-Acetoxyethoxymethyl)-2-formamido-6-(p-tolylsulfonyloxy)purine

S. Belyakov, M. Ikaunieks and M. Madre

The title compound, C₁₈H₁₉N₅O₇S, can be considered as a synthetic analogue of nucleosides. The molecule displays an anti conformation. The occurrence of N—H

O hydrogen bonds results in the formation of centrosymmetric dimers. The crystal packing is characterized by π–π stacking interactions between the purine systems.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030175/dn6253sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030175/dn6253Isup2.hkl Contains datablock I

CCDC reference: 287552

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.056
wR factor = 0.129
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The present crystallographic analysis of the title compound, (I), extends our ongoing investigation of the synthesis of C-6 aryl purine derivatives using the Suzuki–Miyaura reaction, i.e. the Pd-mediated cross-coupling of haloaromatics or aryltriflates with an aryl boronic acid (Miyaura & Suzuki 1995; Suzuki, 1999). This method has led to the development of several biologically active nucleoside analogues, which are generally prepared using 6-chloropurines as substrates (Česnek et al., 2000). Commercially available 6-chloroguanosine derivatives are expensive, but their preparation via chlorination of 6-oxopurines proceeds mostly with low yields. Therefore, the development of O⁶-tosylated guanine derivatives as alternative substrates for cross-coupling reactions is important (Lakshman et al., 2002). We report here the single-crystal structure of an O⁶-tosylate derivative, (I), of acyclic guanosine, as a typical example of the class of intermediates synthesized by tosylation of N²-amidine-protected 9-(2-acetoxyethoxymethyl)guanine and related analogues. The chemical structures of O⁶-tosylates of acyclic guanosine analogues have not been confirmed in the literature by single-crystal X-ray diffraction analysis.

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles of (I) compare well with those of related compounds extracted from the Cambridge Structural Database (CSD, Version 5.26; Allen, 2002). Only 18 entries containing 9-oxymethylpurine derivatives could be found. Selected torsion angles for (I) are reported in Table 1. The value of 77.1 (3)° observed for C8—N9—C24—O25 indicates that the purine system exhibits the anti conformation across the pseudo-glycosidic bond.

The packing of the molecules in the crystal structure of (I) viewed down the a axis is shown in Fig. 2. Intermolecular N—H···O hydrogen bonds result in the formation of centrosymmetric dimers. Slipped π–π stacking interactions are observed between purine systems related by an inversion centre (Fig. 2). The distance between the planes of these overlaped purine fragments is 3.358 (3) Å, whereas the centroid-to-centroid distance is 3.658 Å [symmetry code: −x + 2, −y + 1, −z + 1].

Experimental top

4-Toluenesulfonylchloride (0.25 g, 1.3 mmol) was added at 273 K to a solution containing 9-(2-acetoxyethoxymethyl)-2-(N,N-dimethylimidoformamido)-6-oxopurine (0.16 g, 0.5 mmol), DMAP (Please define; 15.3 mg, 0.13 mmol), NEt₃ (0.19 g, 1.85 mmol) and dichloromethane (10 ml). After the mixture had been allowed to reach ambient temperature, stirring was continued for 4 h. It was then washed with aqueous NaHCO₃ (1 × 2 ml) and water (2 × 2 ml). The organic layer was dried (MgSO₄) and evaporated under reduced pressure. The residue was dissolved in dichloromethane and subjected to column chromatography (silica gel, CH₂Cl₂–EtOH 100:1), and crystallized from ethanol (yield 0.29 g, 79%; m.p. 436–438 K). Spectroscopic analysis: ¹H NMR (200 MHz, DMSO-d₆, δ): 11.26 (d, 1H, J = 10.3 Hz, NH), 9.08 (d, 1H, J = 10.3 Hz, CH), 8.58 (s, 1H, CH), 8.09 (d, 2H, C₆H₄), 7.51 (d, 2H, C₆H₄), 5.59 (s, 2H, NCH₂), 4.09–4.01 (m, 2H, CH₂), 3.75–3.68 (m, 2H, CH₂), 2.43 (s, 3H, CH₃), 1.88 (s, 3H, OAc). Analysis calculated for C₁₈H₁₉N₅O₇S: C 48.10, H 4.26, N 15.58%: found: C 48.47, H 4.31, N 15.73%. Crystals of (I) suitable for X-ray structure analysis were obtained by slow evaporation from an EtOH–H₂O (2:1) solution at room temperature.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and SCALEPAK (Otwinowski & Minor, 1997); program(s) used to solve structure: DIRDIF96 (Beurskens et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: maXus (Mackay et al., 1999) and SHELXL97.

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms are represented by spheres of arbitrary radii.
	Fig. 2. A packing diagram for (I), viewed down the a axis. Dashed lines show hydrogen bonding. For the sake of clarity, H atoms not involved in the hydrogen bonds have been omitted.

9-(2-Acetoxyethoxymethyl)-2-formamido-6-(4-toluenesulfonyl)oxypurine top

Crystal data top

C₁₈H₁₉N₅O₇S	F(000) = 936
M_r = 449.44	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4435 reflections
a = 10.4397 (3) Å	θ = 1.0–27.5°
b = 10.8046 (3) Å	µ = 0.21 mm⁻¹
c = 17.8259 (7) Å	T = 293 K
β = 92.5932 (12)°	Needle, colourless
V = 2008.65 (11) Å³	0.31 × 0.08 × 0.07 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	R_int = 0.036
Radiation source: fine-focus sealed tube	θ_max = 27.5°
ϕ and ω scans	h = −13→13
8435 measured reflections	k = −12→13
4539 independent reflections	l = −23→23
3215 reflections with I > 2σ(I)

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0341P)² + 1.0912P] where P = (F_o² + 2F_c²)/3
4539 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₉N₅O₇S	V = 2008.65 (11) Å³
M_r = 449.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4397 (3) Å	µ = 0.21 mm⁻¹
b = 10.8046 (3) Å	T = 293 K
c = 17.8259 (7) Å	0.31 × 0.08 × 0.07 mm
β = 92.5932 (12)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3215 reflections with I > 2σ(I)
8435 measured reflections	R_int = 0.036
4539 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.13	Δρ_max = 0.22 e Å⁻³
4539 reflections	Δρ_min = −0.26 e Å⁻³
282 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S14	0.55890 (6)	0.68629 (6)	0.39233 (4)	0.0506 (2)
N3	1.05770 (17)	0.63145 (16)	0.43073 (10)	0.0361 (4)
O25	1.24505 (17)	0.42047 (16)	0.30720 (10)	0.0523 (5)
O13	0.66492 (15)	0.57651 (14)	0.40495 (11)	0.0492 (4)
O28	1.43384 (17)	0.35773 (16)	0.20441 (10)	0.0526 (4)
O12	1.16224 (17)	0.95714 (15)	0.52254 (11)	0.0548 (5)
N7	0.8559 (2)	0.38003 (17)	0.36786 (12)	0.0458 (5)
N1	0.83974 (18)	0.70322 (16)	0.43803 (11)	0.0396 (4)
N9	1.06760 (18)	0.41967 (16)	0.38531 (11)	0.0406 (4)
N10	1.00882 (18)	0.82823 (17)	0.47505 (11)	0.0408 (5)
H10	0.9522	0.8856	0.4779	0.049*
O30	1.4215 (2)	0.5537 (2)	0.16451 (14)	0.0794 (7)
C4	1.0053 (2)	0.52569 (19)	0.40496 (12)	0.0344 (5)
O15	0.44770 (18)	0.6167 (2)	0.37159 (13)	0.0698 (6)
O16	0.6090 (2)	0.77441 (19)	0.34273 (12)	0.0670 (6)
C2	0.9682 (2)	0.71425 (19)	0.44615 (13)	0.0360 (5)
C8	0.9720 (2)	0.3373 (2)	0.36364 (14)	0.0467 (6)
H8	0.9891	0.2575	0.3473	0.056*
C22	0.6035 (2)	0.8581 (2)	0.50152 (17)	0.0514 (6)
H22	0.6576	0.8966	0.4687	0.062*
C11	1.1299 (2)	0.8557 (2)	0.49892 (14)	0.0438 (6)
H11	1.1918	0.7939	0.4972	0.053*
C5	0.8751 (2)	0.50019 (19)	0.39418 (13)	0.0369 (5)
C6	0.7953 (2)	0.5964 (2)	0.41197 (13)	0.0385 (5)
C21	0.5839 (3)	0.9083 (2)	0.57099 (18)	0.0573 (7)
H21	0.6262	0.9811	0.5850	0.069*
C17	0.5415 (2)	0.7494 (2)	0.48142 (16)	0.0455 (6)
C26	1.2329 (3)	0.3137 (3)	0.26141 (16)	0.0533 (6)
H26A	1.1431	0.2947	0.2508	0.064*
H26B	1.2729	0.2433	0.2869	0.064*
C20	0.5025 (3)	0.8534 (2)	0.62082 (17)	0.0556 (7)
C18	0.4610 (3)	0.6914 (3)	0.53024 (18)	0.0598 (7)
H18	0.4202	0.6178	0.5166	0.072*
C29	1.4836 (3)	0.4699 (3)	0.19077 (16)	0.0538 (7)
C19	0.4423 (3)	0.7442 (3)	0.59913 (19)	0.0665 (8)
H19	0.3879	0.7056	0.6318	0.080*
C27	1.2982 (3)	0.3398 (3)	0.18940 (16)	0.0590 (7)
H27A	1.2844	0.2711	0.1550	0.071*
H27B	1.2614	0.4135	0.1660	0.071*
C24	1.2059 (2)	0.4027 (2)	0.38036 (14)	0.0479 (6)
H24A	1.2505	0.4609	0.4137	0.057*
H24B	1.2289	0.3197	0.3968	0.057*
C23	0.4792 (4)	0.9119 (3)	0.6961 (2)	0.0776 (9)
H23A	0.4277	0.8574	0.7248	0.116*
H23B	0.4352	0.9892	0.6884	0.116*
H23C	0.5598	0.9261	0.7227	0.116*
C31	1.6233 (3)	0.4727 (3)	0.2095 (2)	0.0732 (9)
H31A	1.6531	0.5567	0.2087	0.110*
H31B	1.6673	0.4248	0.1733	0.110*
H31C	1.6399	0.4384	0.2587	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S14	0.0394 (3)	0.0482 (4)	0.0632 (4)	−0.0016 (3)	−0.0079 (3)	−0.0005 (3)
N3	0.0369 (10)	0.0326 (9)	0.0388 (11)	−0.0047 (7)	0.0026 (8)	−0.0014 (8)
O25	0.0519 (11)	0.0483 (10)	0.0577 (11)	−0.0042 (8)	0.0136 (9)	−0.0107 (8)
O13	0.0346 (9)	0.0385 (9)	0.0746 (12)	−0.0058 (7)	0.0020 (8)	−0.0050 (8)
O28	0.0502 (10)	0.0513 (10)	0.0569 (11)	0.0032 (8)	0.0109 (8)	0.0041 (8)
O12	0.0498 (10)	0.0421 (10)	0.0722 (13)	−0.0128 (8)	−0.0011 (9)	−0.0115 (9)
N7	0.0466 (12)	0.0347 (10)	0.0566 (13)	−0.0090 (9)	0.0083 (10)	−0.0074 (9)
N1	0.0354 (10)	0.0344 (10)	0.0494 (12)	−0.0029 (8)	0.0044 (8)	−0.0013 (8)
N9	0.0425 (11)	0.0332 (9)	0.0465 (12)	−0.0004 (8)	0.0061 (9)	−0.0028 (8)
N10	0.0394 (11)	0.0319 (9)	0.0511 (12)	−0.0042 (8)	0.0025 (9)	−0.0065 (8)
O30	0.0832 (16)	0.0523 (12)	0.1022 (18)	0.0074 (11)	0.0002 (13)	0.0137 (12)
C4	0.0381 (12)	0.0331 (11)	0.0323 (11)	−0.0021 (9)	0.0058 (9)	0.0019 (9)
O15	0.0430 (11)	0.0746 (13)	0.0901 (16)	−0.0087 (9)	−0.0172 (10)	−0.0156 (11)
O16	0.0708 (13)	0.0638 (12)	0.0658 (13)	−0.0003 (10)	−0.0031 (10)	0.0128 (10)
C2	0.0384 (12)	0.0320 (11)	0.0381 (12)	−0.0042 (9)	0.0057 (9)	0.0002 (9)
C8	0.0537 (15)	0.0345 (12)	0.0526 (15)	−0.0063 (10)	0.0108 (12)	−0.0052 (10)
C22	0.0408 (14)	0.0410 (13)	0.0724 (19)	−0.0064 (10)	0.0034 (12)	0.0033 (12)
C11	0.0440 (14)	0.0371 (12)	0.0505 (14)	−0.0068 (10)	0.0053 (11)	−0.0019 (10)
C5	0.0386 (12)	0.0322 (11)	0.0401 (12)	−0.0056 (9)	0.0036 (9)	−0.0004 (9)
C6	0.0358 (12)	0.0370 (12)	0.0428 (13)	−0.0062 (9)	0.0034 (10)	0.0025 (9)
C21	0.0514 (16)	0.0432 (14)	0.077 (2)	−0.0048 (12)	0.0004 (14)	−0.0073 (13)
C17	0.0324 (12)	0.0375 (12)	0.0661 (17)	0.0008 (9)	−0.0026 (11)	0.0003 (11)
C26	0.0498 (15)	0.0529 (15)	0.0577 (16)	−0.0057 (12)	0.0083 (12)	−0.0093 (12)
C20	0.0460 (15)	0.0495 (15)	0.0711 (19)	0.0112 (12)	0.0000 (13)	0.0015 (13)
C18	0.0532 (16)	0.0461 (14)	0.080 (2)	−0.0163 (12)	0.0061 (15)	−0.0018 (14)
C29	0.0627 (17)	0.0498 (15)	0.0497 (16)	0.0016 (13)	0.0112 (13)	−0.0026 (12)
C19	0.0610 (19)	0.0642 (18)	0.076 (2)	−0.0102 (14)	0.0183 (16)	0.0060 (16)
C27	0.0508 (16)	0.0748 (19)	0.0517 (16)	−0.0028 (14)	0.0056 (13)	−0.0055 (14)
C24	0.0438 (14)	0.0519 (14)	0.0480 (15)	0.0062 (11)	0.0014 (11)	−0.0068 (11)
C23	0.084 (2)	0.073 (2)	0.076 (2)	0.0162 (18)	0.0094 (18)	−0.0101 (17)
C31	0.0613 (19)	0.086 (2)	0.072 (2)	−0.0131 (17)	0.0022 (16)	0.0008 (17)

Geometric parameters (Å, º) top

S14—O16	1.416 (2)	C22—C17	1.380 (3)
S14—O15	1.4180 (19)	C22—H22	0.9300
S14—O13	1.6310 (17)	C11—H11	0.9300
S14—C17	1.745 (3)	C5—C6	1.379 (3)
N3—C2	1.331 (3)	C21—C20	1.389 (4)
N3—C4	1.339 (3)	C21—H21	0.9300
O25—C24	1.398 (3)	C17—C18	1.387 (4)
O25—C26	1.416 (3)	C26—C27	1.507 (4)
O13—C6	1.378 (3)	C26—H26A	0.9700
O28—C29	1.345 (3)	C26—H26B	0.9700
O28—C27	1.442 (3)	C20—C19	1.384 (4)
O12—C11	1.217 (3)	C20—C23	1.512 (4)
N7—C8	1.302 (3)	C18—C19	1.376 (4)
N7—C5	1.392 (3)	C18—H18	0.9300
N1—C6	1.321 (3)	C29—C31	1.481 (4)
N1—C2	1.348 (3)	C19—H19	0.9300
N9—C4	1.371 (3)	C27—H27A	0.9700
N9—C8	1.379 (3)	C27—H27B	0.9700
N9—C24	1.462 (3)	C24—H24A	0.9700
N10—C11	1.348 (3)	C24—H24B	0.9700
N10—C2	1.393 (3)	C23—H23A	0.9600
N10—H10	0.8600	C23—H23B	0.9600
O30—C29	1.197 (3)	C23—H23C	0.9600
C4—C5	1.391 (3)	C31—H31A	0.9600
C8—H8	0.9300	C31—H31B	0.9600
C22—C21	1.376 (4)	C31—H31C	0.9600

O16—S14—O15	121.01 (14)	C18—C17—S14	119.0 (2)
O16—S14—O13	107.91 (11)	O25—C26—C27	107.8 (2)
O15—S14—O13	101.12 (11)	O25—C26—H26A	110.1
O16—S14—C17	111.22 (12)	C27—C26—H26A	110.1
O15—S14—C17	109.08 (13)	O25—C26—H26B	110.1
O13—S14—C17	104.86 (11)	C27—C26—H26B	110.1
C2—N3—C4	111.39 (18)	H26A—C26—H26B	108.5
C24—O25—C26	113.80 (19)	C19—C20—C21	117.9 (3)
C6—O13—S14	124.08 (14)	C19—C20—C23	121.0 (3)
C29—O28—C27	118.1 (2)	C21—C20—C23	121.1 (3)
C8—N7—C5	103.31 (19)	C19—C18—C17	119.2 (3)
C6—N1—C2	116.58 (19)	C19—C18—H18	120.4
C4—N9—C8	105.38 (19)	C17—C18—H18	120.4
C4—N9—C24	126.99 (19)	O30—C29—O28	123.0 (3)
C8—N9—C24	127.3 (2)	O30—C29—C31	125.7 (3)
C11—N10—C2	125.2 (2)	O28—C29—C31	111.2 (3)
C11—N10—H10	117.4	C18—C19—C20	121.4 (3)
C2—N10—H10	117.4	C18—C19—H19	119.3
N3—C4—N9	127.6 (2)	C20—C19—H19	119.3
N3—C4—C5	126.7 (2)	O28—C27—C26	110.2 (2)
N9—C4—C5	105.73 (18)	O28—C27—H27A	109.6
N3—C2—N1	128.51 (19)	C26—C27—H27A	109.6
N3—C2—N10	117.76 (19)	O28—C27—H27B	109.6
N1—C2—N10	113.73 (19)	C26—C27—H27B	109.6
N7—C8—N9	114.7 (2)	H27A—C27—H27B	108.1
N7—C8—H8	122.6	O25—C24—N9	111.8 (2)
N9—C8—H8	122.6	O25—C24—H24A	109.3
C21—C22—C17	118.8 (3)	N9—C24—H24A	109.3
C21—C22—H22	120.6	O25—C24—H24B	109.3
C17—C22—H22	120.6	N9—C24—H24B	109.3
O12—C11—N10	123.3 (2)	H24A—C24—H24B	107.9
O12—C11—H11	118.4	C20—C23—H23A	109.5
N10—C11—H11	118.4	C20—C23—H23B	109.5
C6—C5—C4	114.58 (19)	H23A—C23—H23B	109.5
C6—C5—N7	134.6 (2)	C20—C23—H23C	109.5
C4—C5—N7	110.85 (19)	H23A—C23—H23C	109.5
N1—C6—O13	119.9 (2)	H23B—C23—H23C	109.5
N1—C6—C5	122.2 (2)	C29—C31—H31A	109.5
O13—C6—C5	117.81 (19)	C29—C31—H31B	109.5
C22—C21—C20	121.8 (3)	H31A—C31—H31B	109.5
C22—C21—H21	119.1	C29—C31—H31C	109.5
C20—C21—H21	119.1	H31A—C31—H31C	109.5
C22—C17—C18	120.8 (3)	H31B—C31—H31C	109.5
C22—C17—S14	120.1 (2)

N1—C2—N10—C11	169.5 (2)	C8—N9—C24—O25	77.6 (3)
C2—N10—C11—O12	178.6 (2)	N9—C24—O25—C26	−84.9 (3)
C6—O13—S14—O15	167.0 (2)	C24—O25—C26—C27	−170.8 (2)
C6—O13—S14—O16	39.0 (2)	O25—C26—C27—O28	64.6 (3)
C6—O13—S14—C17	−79.6 (2)	C26—C27—O28—C29	−115.3 (3)
O13—S14—C17—C18	−82.3 (2)	C27—O28—C29—O30	−2.6 (4)
O13—S14—C17—C22	100.1 (2)	C27—O28—C29—C31	179.7 (2)
C4—N9—C24—O25	−94.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O12ⁱ	0.86	2.08	2.928 (3)	171

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₅O₇S
M_r	449.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.4397 (3), 10.8046 (3), 17.8259 (7)
β (°)	92.5932 (12)
V (Å³)	2008.65 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.31 × 0.08 × 0.07

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8435, 4539, 3215
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.129, 1.13
No. of reflections	4539
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.26

Computer programs: KappaCCD Server Software (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor 1997), DENZO and SCALEPAK (Otwinowski & Minor, 1997), DIRDIF96 (Beurskens et al., 1996), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003), maXus (Mackay et al., 1999) and SHELXL97.

Selected torsion angles (º) top

N1—C2—N10—C11	169.5 (2)	C8—N9—C24—O25	77.6 (3)
C2—N10—C11—O12	178.6 (2)	N9—C24—O25—C26	−84.9 (3)
C6—O13—S14—O15	167.0 (2)	C24—O25—C26—C27	−170.8 (2)
C6—O13—S14—O16	39.0 (2)	O25—C26—C27—O28	64.6 (3)
C6—O13—S14—C17	−79.6 (2)	C26—C27—O28—C29	−115.3 (3)
O13—S14—C17—C18	−82.3 (2)	C27—O28—C29—O30	−2.6 (4)
O13—S14—C17—C22	100.1 (2)	C27—O28—C29—C31	179.7 (2)
C4—N9—C24—O25	−94.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O12ⁱ	0.86	2.08	2.928 (3)	171

Symmetry code: (i) −x+2, −y+2, −z+1.

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