Multicomponent pharmaceutical cocrystals: furosemide and pentoxifylline

The combination of the active pharmaceutical ingredients furosemide [4-chloro-2-(furan-2-yl­methyl­amino)-5-sulfamoyl­benzoic acid] and pentoxifylline [3,7-dimethyl-1-(5-oxohex­yl)-3,7-dihydro-1H-purine-2,6-dione] produces a 1:1 cocrystal, C₁₂H₁₁ClN₂O₅S·C₁₃H₁₈N₄O₃, (I), a 1:1 cocrystal hydrate, C₁₂H₁₁ClN₂O₅S·C₁₃H₁₈N₄O₃·H₂O, (II), and a 1:1 cocrystal acetone solvate, C₁₂H₁₁ClN₂O₅S·C₁₃H₁₈N₄O₃·C₂H₆O, (III). These structures exhibit the presence of a rarely encountered synthon with the graph set R₂²(7). All potential hydrogen-bond donors of furosemide participate in hydrogen-bond formation in (I)–(III). However, only two hydrogen-bond acceptors of furosemide are active in (I) and (II), and only one is active in (III). Four hydrogen-bond acceptors of pentoxifylline are active in (II), three in (I) and two in (III). These observations are in good agreement with the calculated packing indexes of 69.5, 69.6 and 68.8% for (II), (I) and (III), respectively.

S1. Comment

As an alternative to pharmaceutical fixed-dosage combinations, it is possible to assemble different active pharmaceutical ingredients in one crystal lattice by cocrystallization. In this work, we present cocrystals (I)–(III) of the cardiovascular drugs furosemide and pentoxifylline. The former is an important loop diuretic (Agyralides et al., 2004) and the latter is indicated to treat intermittent claudication resulting from obstructed arteries in the limbs (Nieder et al., 2005).

The bond lengths and angles in the molecules of (I)–(III) are close to standard values (Allen et al. 1987).

Besides the pharmaceutical importance of the cocrystals obtained, it was interesting to observe the influence of the crystal environment on the molecular conformations of the furosemide and pentoxifylline molecules by comparison of the corresponding conformations in single- and multicomponent crystal structures. There are two polymorphic forms of pentoxifylline reported in the literature, namely triclinic (Pavelčík et al., 1989) and monoclinic (Stepanovs & Mishnev, 2011), and three polymorphic forms of furosemide have been reported by Lamotte et al. (1978) and Babu et al. (2010). One can see that in (I)–(III), the pentoxifylline molecule adopts a conformation close to that in the monoclinic form, while the torsion angles of furosemide vary in a wide range (Table 1). Apparently, due to its flexibility, furosemide can be considered as a useful coformer, capable of adopting the conformation required for a particular crystalline environment and content.

For convenience, we denote the purine bicycle of the pentoxifylline molecule by A+B and the benzene and furan rings by C and D, respectively. The dihedral angle between the A+B and C mean planes is 3.8° in (I), 7.4° in (II) and 22.9° in (III). The C/D angle is close to 85° in all furosemide polymorphs, but in cocrystals (I)–(III) its value lies between 58.8 and 79.8°.

π–π stacking interactions are present in (I)–(III). The centroid–centroid distance between furosemide ring C and the five-membered ring of the pentoxifylline purine system A+B is 3.65 Å in (I) and the centroid–centroid distances between purine systems is 3.51 Å in (III). No π–π stacking interactions were observed in the (II).

In (I)–(III), three hydrogen-bond donors of furosemide participate in the formation of an intermolecular hydrogen bond. Four furosemide hydrogen-bond acceptors are active in (II) and only three are active in (I) and (III). For pentoxifylline, the highest number of active hydrogen-bond acceptors (four) is observed in (II), three hydrogen-bond acceptors are active in (I) and two in (III). There is one hydrogen-bond donor in pentoxifylline in (I)–(III). The hydrogen-bonding geometry in (I)–(III) is presented in Tables 2, 3 and 4, respectively. In all three crystal structures, an intramolecular N15—H···O13 hydrogen bond is present in the furosemide molecule. Atom N2 participates as a hydrogen-bond donor in two hydrogen bonds, where atoms O35 and O36 are acceptors. An N2—H···O36 hydrogen bond is present in (I) but absent in (II) and (III). All three structures exhibit the rarely encountered R₂²(7) graph-set motif (Bernstein et al., 1995).

In (II), the water molecules connect the pentoxifylline molecules into infinite chains along the crystallographic b axis by strong O—H···O hydrogen bonds. In (III), the acetone solvent molecule participates in N—H···O hydrogen bonding with the amino group of furosemide.

It should be noted that the packing index (the percentage of filled space) (Spek, 2009) has the largest value of 69.6% for (II) and corresponds to the maximum number of realized hydrogen bonds; the packing index is 69.5% for (I) and 68.8% for (III)

Related literature

For related literature, see: Agyralides et al. (2004); Allen et al. (1987); Babu et al. (2010); Bernstein et al. (1995); Lamotte et al. (1978); Nieder et al. (2005); Pavelčík et al. (1989); Spek (2009); Stepanovs & Mishnev (2011).

S2. Experimental

Furosemide was obtained by recrystallization of `Furosemīds Olainfarm' tablets, produced by JSC Olainfarm, Latvia. Pentoxifylline was obtained by recrystallization of `Trental' tablets, produced by Sanofi–Aventis Deutschland GmbH. Crystals suitable for single-crystal X-ray analysis were grown at room temperature by slow evaporation from methanol for (I), rectified ethanol for (II) and acetone for (III). The molar ratio of furosemide and pentoxifylline in each case was 1:1.

S3. Refinement

All H atoms were positioned geometrically, with C—H = 0.93 or 0.97 Å, and refined as riding on their parent atoms, with U_iso(H) = 1.5U_eq(C) for methyl groups and 1.2U_eq(C) otherwise.

Computing details

For all compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The structure of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. The structure of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. The R2^2(7) hydrogen-bond motif between furosemide and pentoxifylline molecules in (I)–(III). Dashed lines indicate hydrogen bonds.

(I) 4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid–3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione (1/1)

Crystal data

C12H11ClN2O5S·C13H18N4O3	F(000) = 1272
Mr = 609.06	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Melting point: 436 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.0948 (2) Å	Cell parameters from 14368 reflections
b = 9.3747 (2) Å	θ = 1.0–27.5°
c = 36.291 (1) Å	µ = 0.28 mm^−1
β = 93.128 (1)°	T = 190 K
V = 2749.89 (12) Å^3	Plate, colourless
Z = 4	0.50 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3111 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
CCD scans	h = −10→10
10068 measured reflections	k = −12→11
6133 independent reflections	l = −47→47

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 0.1315P] where P = (Fo^2 + 2Fc^2)/3
6133 reflections	(Δ/σ)max = 0.002
373 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−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 for ALL reflections except those flagged by the user for potential systematic errors. 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	−0.07863 (12)	0.08818 (9)	0.08738 (3)	0.0306 (3)
N2	−0.1954 (4)	0.1235 (3)	0.12076 (9)	0.0346 (8)
H2A	−0.2929	0.0735	0.1162	0.042*
H2B	−0.2195	0.2088	0.1224	0.042*
O3	0.0634 (3)	0.1801 (2)	0.09131 (8)	0.0371 (7)
O4	−0.1689 (3)	0.0854 (2)	0.05227 (7)	0.0410 (8)
C5	−0.0177 (4)	−0.0894 (3)	0.09658 (10)	0.0255 (9)
C6	−0.0733 (4)	−0.1927 (3)	0.07155 (10)	0.0244 (9)
H6	−0.1396	−0.1647	0.0511	0.029*
C7	−0.0343 (4)	−0.3354 (3)	0.07570 (10)	0.0234 (8)
C8	0.0675 (4)	−0.3804 (3)	0.10658 (10)	0.0224 (8)
C9	0.1272 (4)	−0.2733 (3)	0.13152 (10)	0.0253 (9)
H9	0.1978	−0.2988	0.1515	0.030*
C10	0.0830 (4)	−0.1333 (3)	0.12680 (10)	0.0261 (9)
Cl11	0.15463 (13)	−0.01374 (9)	0.16052 (3)	0.0412 (3)
C12	−0.1052 (4)	−0.4400 (4)	0.04838 (10)	0.0257 (9)
O13	−0.0858 (4)	−0.5672 (2)	0.05059 (8)	0.0437 (8)
O14	−0.1944 (3)	−0.3797 (2)	0.02117 (7)	0.0392 (8)
H14	−0.2404	−0.4416	0.0084	0.059*
N15	0.1083 (4)	−0.5179 (3)	0.11249 (8)	0.0301 (8)
H15	0.0724	−0.5789	0.0963	0.036*
C16	0.2082 (4)	−0.5723 (4)	0.14408 (11)	0.0300 (9)
H16A	0.3120	−0.5203	0.1459	0.036*
H16B	0.2338	−0.6717	0.1396	0.036*
C17	0.1284 (4)	−0.5613 (4)	0.18023 (12)	0.0298 (10)
O18	−0.0101 (3)	−0.6395 (3)	0.18542 (9)	0.0513 (8)
C19	−0.0512 (6)	−0.6100 (5)	0.22121 (14)	0.0522 (13)
H19	−0.1402	−0.6500	0.2327	0.063*
C20	0.0524 (6)	−0.5184 (5)	0.23657 (13)	0.0500 (12)
H20	0.0495	−0.4806	0.2602	0.060*
C21	0.1709 (5)	−0.4876 (4)	0.21004 (11)	0.0308 (9)
H21	0.2613	−0.4267	0.2132	0.037*
C22	0.4497 (5)	−0.3405 (5)	0.30488 (13)	0.0546 (13)
H22A	0.3443	−0.3006	0.3101	0.082*
H22B	0.5297	−0.3161	0.3244	0.082*
H22C	0.4404	−0.4424	0.3031	0.082*
C23	0.5036 (5)	−0.2823 (4)	0.26929 (13)	0.0393 (11)
O24	0.4185 (4)	−0.1977 (3)	0.25107 (9)	0.0581 (9)
C25	0.6657 (5)	−0.3319 (4)	0.25653 (11)	0.0321 (10)
H25A	0.6643	−0.4353	0.2557	0.039*
H25B	0.7515	−0.3039	0.2748	0.039*
C26	0.7129 (4)	−0.2769 (4)	0.21915 (11)	0.0311 (9)
H26A	0.8279	−0.3006	0.2159	0.037*
H26B	0.7037	−0.1737	0.2190	0.037*
C27	0.6080 (4)	−0.3362 (4)	0.18638 (10)	0.0312 (10)
H27A	0.5857	−0.4366	0.1903	0.037*
H27B	0.5030	−0.2861	0.1841	0.037*
C28	0.7000 (5)	−0.3173 (4)	0.15151 (11)	0.0348 (10)
H28A	0.7423	−0.2206	0.1508	0.042*
H28B	0.7940	−0.3815	0.1523	0.042*
N29	0.5977 (3)	−0.3444 (3)	0.11744 (8)	0.0276 (7)
C30	0.5810 (5)	−0.4872 (4)	0.10670 (11)	0.0294 (9)
N31	0.4856 (4)	−0.5148 (3)	0.07496 (8)	0.0297 (8)
C32	0.4134 (4)	−0.4033 (3)	0.05534 (10)	0.0256 (8)
C33	0.4357 (4)	−0.2650 (3)	0.06613 (10)	0.0256 (9)
C34	0.5272 (4)	−0.2248 (4)	0.09883 (11)	0.0294 (9)
O35	0.5474 (3)	−0.1032 (3)	0.11097 (8)	0.0382 (7)
O36	0.6472 (3)	−0.5820 (3)	0.12492 (8)	0.0395 (7)
C37	0.4594 (5)	−0.6632 (3)	0.06319 (12)	0.0396 (11)
H37A	0.3773	−0.7063	0.0777	0.059*
H37B	0.5613	−0.7150	0.0665	0.059*
H37C	0.4223	−0.6652	0.0376	0.059*
N38	0.3152 (4)	−0.4143 (3)	0.02412 (8)	0.0298 (8)
C39	0.2766 (5)	−0.2779 (4)	0.01568 (11)	0.0311 (9)
H39	0.2096	−0.2511	−0.0048	0.037*
N40	0.3449 (4)	−0.1857 (3)	0.03989 (9)	0.0286 (8)
C41	0.3315 (5)	−0.0295 (3)	0.03834 (12)	0.0400 (11)
H41A	0.2598	−0.0025	0.0176	0.060*
H41B	0.4392	0.0111	0.0358	0.060*
H41C	0.2869	0.0049	0.0606	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0420 (6)	0.0157 (4)	0.0340 (7)	0.0018 (4)	0.0010 (5)	−0.0004 (4)
N2	0.038 (2)	0.0201 (15)	0.046 (2)	0.0037 (14)	0.0063 (16)	−0.0090 (14)
O3	0.0408 (17)	0.0170 (12)	0.054 (2)	−0.0057 (11)	0.0036 (14)	−0.0008 (12)
O4	0.067 (2)	0.0201 (13)	0.0338 (19)	0.0054 (12)	−0.0127 (15)	0.0023 (11)
C5	0.031 (2)	0.0175 (17)	0.028 (2)	−0.0050 (16)	−0.0001 (18)	−0.0020 (16)
C6	0.032 (2)	0.0172 (17)	0.025 (2)	0.0023 (15)	0.0055 (17)	0.0024 (15)
C7	0.027 (2)	0.0169 (17)	0.026 (2)	0.0015 (15)	0.0012 (17)	−0.0015 (15)
C8	0.022 (2)	0.0180 (17)	0.027 (2)	−0.0003 (14)	0.0057 (17)	0.0002 (15)
C9	0.025 (2)	0.0209 (18)	0.029 (2)	0.0001 (15)	−0.0052 (17)	0.0043 (16)
C10	0.028 (2)	0.0223 (18)	0.028 (2)	−0.0032 (15)	0.0002 (17)	−0.0041 (16)
Cl11	0.0534 (7)	0.0284 (5)	0.0401 (7)	−0.0039 (5)	−0.0129 (5)	−0.0097 (5)
C12	0.028 (2)	0.024 (2)	0.024 (2)	0.0009 (16)	0.0000 (17)	0.0007 (16)
O13	0.070 (2)	0.0146 (13)	0.044 (2)	0.0032 (13)	−0.0174 (16)	−0.0032 (12)
O14	0.0570 (19)	0.0210 (13)	0.0374 (19)	0.0018 (12)	−0.0162 (15)	−0.0056 (12)
N15	0.037 (2)	0.0165 (15)	0.036 (2)	0.0010 (13)	−0.0054 (16)	−0.0022 (13)
C16	0.030 (2)	0.0244 (18)	0.035 (3)	0.0022 (16)	−0.0062 (19)	0.0036 (17)
C17	0.016 (2)	0.028 (2)	0.046 (3)	0.0011 (16)	0.0002 (18)	0.0128 (19)
O18	0.0380 (18)	0.0483 (17)	0.068 (3)	−0.0048 (14)	0.0034 (17)	0.0054 (16)
C19	0.044 (3)	0.055 (3)	0.060 (4)	0.012 (2)	0.026 (3)	0.017 (3)
C20	0.060 (3)	0.047 (3)	0.043 (3)	0.014 (2)	−0.001 (3)	0.003 (2)
C21	0.025 (2)	0.0250 (19)	0.041 (3)	−0.0069 (16)	−0.0066 (19)	−0.0003 (18)
C22	0.050 (3)	0.073 (3)	0.042 (3)	0.010 (2)	0.012 (2)	0.005 (3)
C23	0.037 (3)	0.040 (2)	0.041 (3)	0.000 (2)	−0.003 (2)	−0.011 (2)
O24	0.055 (2)	0.070 (2)	0.050 (2)	0.0328 (17)	0.0111 (16)	0.0073 (17)
C25	0.035 (2)	0.030 (2)	0.031 (3)	0.0068 (17)	−0.0046 (19)	−0.0055 (17)
C26	0.024 (2)	0.035 (2)	0.034 (3)	−0.0030 (16)	−0.0013 (18)	−0.0028 (18)
C27	0.027 (2)	0.039 (2)	0.028 (3)	−0.0063 (17)	−0.0006 (18)	−0.0053 (18)
C28	0.029 (2)	0.044 (2)	0.031 (3)	−0.0051 (18)	−0.0030 (19)	−0.0041 (19)
N29	0.0225 (17)	0.0297 (17)	0.030 (2)	−0.0033 (13)	0.0008 (14)	−0.0006 (14)
C30	0.030 (2)	0.029 (2)	0.030 (2)	0.0032 (17)	0.0117 (18)	−0.0039 (18)
N31	0.036 (2)	0.0250 (16)	0.028 (2)	0.0041 (14)	−0.0003 (15)	−0.0017 (14)
C32	0.030 (2)	0.0255 (19)	0.021 (2)	−0.0030 (16)	0.0042 (17)	−0.0020 (16)
C33	0.034 (2)	0.0262 (19)	0.017 (2)	0.0005 (16)	0.0024 (18)	−0.0012 (16)
C34	0.023 (2)	0.031 (2)	0.034 (3)	−0.0035 (16)	0.0074 (18)	−0.0040 (18)
O35	0.0405 (17)	0.0301 (15)	0.0438 (19)	−0.0083 (12)	−0.0001 (13)	−0.0088 (13)
O36	0.0427 (18)	0.0382 (15)	0.0372 (19)	0.0114 (13)	−0.0027 (14)	0.0023 (13)
C37	0.054 (3)	0.023 (2)	0.041 (3)	−0.0015 (18)	0.002 (2)	−0.0069 (18)
N38	0.042 (2)	0.0215 (15)	0.026 (2)	0.0026 (14)	0.0009 (16)	−0.0016 (13)
C39	0.039 (2)	0.030 (2)	0.023 (2)	0.0003 (18)	−0.0009 (19)	−0.0034 (17)
N40	0.0319 (19)	0.0240 (16)	0.030 (2)	−0.0023 (13)	0.0049 (15)	−0.0007 (14)
C41	0.053 (3)	0.0196 (19)	0.047 (3)	−0.0031 (18)	0.002 (2)	−0.0030 (18)

Geometric parameters (Å, º)

S1—O4	1.434 (3)	C22—H22C	0.9600
S1—O3	1.438 (2)	C23—O24	1.221 (5)
S1—N2	1.611 (3)	C23—C25	1.490 (6)
S1—C5	1.763 (3)	C25—C26	1.520 (5)
N2—H2A	0.9254	C25—H25A	0.9700
N2—H2B	0.8261	C25—H25B	0.9700
C5—C6	1.386 (4)	C26—C27	1.528 (5)
C5—C10	1.392 (5)	C26—H26A	0.9700
C6—C7	1.381 (4)	C26—H26B	0.9700
C6—H6	0.9300	C27—C28	1.514 (5)
C7—C8	1.418 (5)	C27—H27A	0.9700
C7—C12	1.488 (5)	C27—H27B	0.9700
C8—N15	1.345 (4)	C28—N29	1.472 (4)
C8—C9	1.419 (4)	C28—H28A	0.9700
C9—C10	1.369 (4)	C28—H28B	0.9700
C9—H9	0.9300	N29—C30	1.398 (4)
C10—Cl11	1.736 (3)	N29—C34	1.413 (5)
C12—O13	1.205 (4)	C30—O36	1.215 (4)
C12—O14	1.318 (4)	C30—N31	1.376 (4)
O14—H14	0.8200	N31—C32	1.377 (4)
N15—C16	1.459 (4)	N31—C37	1.467 (4)
N15—H15	0.8600	C32—N38	1.352 (4)
C16—C17	1.497 (5)	C32—C33	1.363 (4)
C16—H16A	0.9700	C33—N40	1.387 (4)
C16—H16B	0.9700	C33—C34	1.416 (5)
C17—C21	1.314 (5)	C34—O35	1.230 (4)
C17—O18	1.360 (4)	C37—H37A	0.9600
O18—C19	1.386 (5)	C37—H37B	0.9600
C19—C20	1.304 (6)	C37—H37C	0.9600
C19—H19	0.9300	N38—C39	1.348 (4)
C20—C21	1.426 (6)	C39—N40	1.331 (4)
C20—H20	0.9300	C39—H39	0.9300
C21—H21	0.9300	N40—C41	1.469 (4)
C22—C23	1.489 (6)	C41—H41A	0.9600
C22—H22A	0.9600	C41—H41B	0.9600
C22—H22B	0.9600	C41—H41C	0.9600
O4—S1—O3	117.72 (16)	C23—C25—C26	116.1 (3)
O4—S1—N2	112.37 (17)	C23—C25—H25A	108.3
O3—S1—N2	107.49 (16)	C26—C25—H25A	108.3
O4—S1—C5	105.95 (15)	C23—C25—H25B	108.3
O3—S1—C5	109.47 (15)	C26—C25—H25B	108.3
N2—S1—C5	102.78 (17)	H25A—C25—H25B	107.4
S1—N2—H2A	106.9	C25—C26—C27	114.5 (3)
S1—N2—H2B	113.8	C25—C26—H26A	108.6
H2A—N2—H2B	107.5	C27—C26—H26A	108.6
C6—C5—C10	117.7 (3)	C25—C26—H26B	108.6
C6—C5—S1	117.3 (3)	C27—C26—H26B	108.6
C10—C5—S1	125.0 (2)	H26A—C26—H26B	107.6
C7—C6—C5	122.8 (3)	C28—C27—C26	109.3 (3)
C7—C6—H6	118.6	C28—C27—H27A	109.8
C5—C6—H6	118.6	C26—C27—H27A	109.8
C6—C7—C8	119.6 (3)	C28—C27—H27B	109.8
C6—C7—C12	119.3 (3)	C26—C27—H27B	109.8
C8—C7—C12	121.1 (3)	H27A—C27—H27B	108.3
N15—C8—C9	120.3 (3)	N29—C28—C27	113.7 (3)
N15—C8—C7	122.6 (3)	N29—C28—H28A	108.8
C9—C8—C7	117.2 (3)	C27—C28—H28A	108.8
C10—C9—C8	121.4 (3)	N29—C28—H28B	108.8
C10—C9—H9	119.3	C27—C28—H28B	108.8
C8—C9—H9	119.3	H28A—C28—H28B	107.7
C9—C10—C5	121.3 (3)	C30—N29—C34	126.6 (3)
C9—C10—Cl11	117.1 (3)	C30—N29—C28	116.2 (3)
C5—C10—Cl11	121.6 (2)	C34—N29—C28	117.2 (3)
O13—C12—O14	122.6 (3)	O36—C30—N31	121.9 (3)
O13—C12—C7	124.3 (3)	O36—C30—N29	121.0 (3)
O14—C12—C7	113.1 (3)	N31—C30—N29	117.0 (3)
C12—O14—H14	109.5	C30—N31—C32	119.6 (3)
C8—N15—C16	125.6 (3)	C30—N31—C37	119.2 (3)
C8—N15—H15	117.2	C32—N31—C37	121.2 (3)
C16—N15—H15	117.2	N38—C32—C33	112.1 (3)
N15—C16—C17	114.6 (3)	N38—C32—N31	126.1 (3)
N15—C16—H16A	108.6	C33—C32—N31	121.8 (3)
C17—C16—H16A	108.6	C32—C33—N40	104.8 (3)
N15—C16—H16B	108.6	C32—C33—C34	123.3 (3)
C17—C16—H16B	108.6	N40—C33—C34	131.7 (3)
H16A—C16—H16B	107.6	O35—C34—N29	121.5 (3)
C21—C17—O18	110.5 (4)	O35—C34—C33	126.9 (3)
C21—C17—C16	130.6 (3)	N29—C34—C33	111.6 (3)
O18—C17—C16	118.8 (3)	N31—C37—H37A	109.5
C17—O18—C19	105.3 (3)	N31—C37—H37B	109.5
C20—C19—O18	110.5 (4)	H37A—C37—H37B	109.5
C20—C19—H19	124.7	N31—C37—H37C	109.5
O18—C19—H19	124.7	H37A—C37—H37C	109.5
C19—C20—C21	106.6 (4)	H37B—C37—H37C	109.5
C19—C20—H20	126.7	C39—N38—C32	103.7 (3)
C21—C20—H20	126.7	N40—C39—N38	112.5 (3)
C17—C21—C20	107.1 (4)	N40—C39—H39	123.7
C17—C21—H21	126.5	N38—C39—H39	123.7
C20—C21—H21	126.5	C39—N40—C33	106.9 (3)
C23—C22—H22A	109.5	C39—N40—C41	126.5 (3)
C23—C22—H22B	109.5	C33—N40—C41	126.6 (3)
H22A—C22—H22B	109.5	N40—C41—H41A	109.5
C23—C22—H22C	109.5	N40—C41—H41B	109.5
H22A—C22—H22C	109.5	H41A—C41—H41B	109.5
H22B—C22—H22C	109.5	N40—C41—H41C	109.5
O24—C23—C22	121.7 (4)	H41A—C41—H41C	109.5
O24—C23—C25	121.0 (4)	H41B—C41—H41C	109.5
C22—C23—C25	117.4 (4)
O4—S1—C5—C6	−4.1 (3)	C22—C23—C25—C26	176.8 (3)
O3—S1—C5—C6	−132.0 (3)	C23—C25—C26—C27	−69.3 (4)
N2—S1—C5—C6	114.0 (3)	C25—C26—C27—C28	−160.3 (3)
O4—S1—C5—C10	175.3 (3)	C26—C27—C28—N29	−168.6 (3)
O3—S1—C5—C10	47.4 (4)	C27—C28—N29—C30	−83.0 (4)
N2—S1—C5—C10	−66.7 (4)	C27—C28—N29—C34	97.4 (4)
C10—C5—C6—C7	0.7 (6)	C34—N29—C30—O36	−179.9 (4)
S1—C5—C6—C7	−179.9 (3)	C28—N29—C30—O36	0.5 (5)
C5—C6—C7—C8	−0.4 (6)	C34—N29—C30—N31	−0.5 (5)
C5—C6—C7—C12	177.4 (3)	C28—N29—C30—N31	179.9 (3)
C6—C7—C8—N15	179.1 (3)	O36—C30—N31—C32	−180.0 (4)
C12—C7—C8—N15	1.5 (5)	N29—C30—N31—C32	0.6 (5)
C6—C7—C8—C9	−1.2 (5)	O36—C30—N31—C37	1.5 (6)
C12—C7—C8—C9	−178.9 (3)	N29—C30—N31—C37	−177.9 (3)
N15—C8—C9—C10	−177.8 (3)	C30—N31—C32—N38	−179.0 (4)
C7—C8—C9—C10	2.6 (5)	C37—N31—C32—N38	−0.6 (6)
C8—C9—C10—C5	−2.3 (6)	C30—N31—C32—C33	1.0 (5)
C8—C9—C10—Cl11	176.5 (3)	C37—N31—C32—C33	179.5 (4)
C6—C5—C10—C9	0.6 (6)	N38—C32—C33—N40	0.2 (4)
S1—C5—C10—C9	−178.7 (3)	N31—C32—C33—N40	−179.9 (3)
C6—C5—C10—Cl11	−178.1 (3)	N38—C32—C33—C34	177.1 (3)
S1—C5—C10—Cl11	2.5 (5)	N31—C32—C33—C34	−3.0 (6)
C6—C7—C12—O13	−176.0 (4)	C30—N29—C34—O35	178.8 (3)
C8—C7—C12—O13	1.7 (6)	C28—N29—C34—O35	−1.6 (5)
C6—C7—C12—O14	3.4 (5)	C30—N29—C34—C33	−1.2 (5)
C8—C7—C12—O14	−179.0 (3)	C28—N29—C34—C33	178.5 (3)
C9—C8—N15—C16	2.2 (5)	C32—C33—C34—O35	−177.1 (4)
C7—C8—N15—C16	−178.2 (3)	N40—C33—C34—O35	−1.1 (7)
C8—N15—C16—C17	67.5 (4)	C32—C33—C34—N29	2.9 (5)
N15—C16—C17—C21	−115.8 (4)	N40—C33—C34—N29	178.9 (4)
N15—C16—C17—O18	65.5 (4)	C33—C32—N38—C39	0.0 (4)
C21—C17—O18—C19	−0.5 (4)	N31—C32—N38—C39	−179.9 (4)
C16—C17—O18—C19	178.4 (3)	C32—N38—C39—N40	−0.2 (4)
C17—O18—C19—C20	1.2 (4)	N38—C39—N40—C33	0.3 (4)
O18—C19—C20—C21	−1.4 (5)	N38—C39—N40—C41	178.3 (3)
O18—C17—C21—C20	−0.3 (4)	C32—C33—N40—C39	−0.3 (4)
C16—C17—C21—C20	−179.0 (3)	C34—C33—N40—C39	−176.8 (4)
C19—C20—C21—C17	1.1 (5)	C32—C33—N40—C41	−178.2 (3)
O24—C23—C25—C26	−2.9 (5)	C34—C33—N40—C41	5.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H15···O13	0.86	2.04	2.710 (4)	134
N15—H15···O3^i	0.86	2.27	2.951 (3)	137
N2—H2A···O35^ii	0.93	2.10	2.983 (4)	158
N2—H2B···O36^iii	0.83	2.24	3.048 (4)	165
C39—H39···O13^iv	0.93	2.55	3.145 (5)	122
C39—H39···O4^v	0.93	2.33	3.141 (5)	145
O14—H14···N38^iv	0.82	1.87	2.685 (4)	171

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

(II) 4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid–3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione– water (1/1/1)

Crystal data

C12H11ClN2O5S·C13H18N4O3·H2O	Z = 2
Mr = 627.08	F(000) = 656
Triclinic, P1	Dx = 1.460 Mg m^−3
Hall symbol: -P 1	Melting point: 435 K
a = 8.4052 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4494 (3) Å	Cell parameters from 1943 reflections
c = 19.6748 (9) Å	θ = 0.8–25.0°
α = 92.649 (1)°	µ = 0.27 mm^−1
β = 99.170 (2)°	T = 190 K
γ = 111.466 (1)°	Plate, colourless
V = 1426.35 (9) Å^3	0.30 × 0.20 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
CCD scans	h = −10→10
10153 measured reflections	k = −12→12
6429 independent reflections	l = −20→25

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.069P)^2 + 1.3485P] where P = (Fo^2 + 2Fc^2)/3
6429 reflections	(Δ/σ)max = 0.001
386 parameters	Δρmax = 0.79 e Å^−3
2 restraints	Δρmin = −0.41 e Å^−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	−0.18998 (14)	0.00259 (10)	0.34191 (6)	0.0290 (3)
N2	−0.3398 (5)	−0.0983 (3)	0.2790 (2)	0.0361 (9)
H2A	−0.4515	−0.0732	0.2717	0.043*
H2B	−0.2781	−0.1212	0.2426	0.043*
O3	−0.2608 (4)	−0.0119 (3)	0.40382 (15)	0.0379 (8)
O4	−0.0432 (4)	−0.0391 (3)	0.33889 (16)	0.0376 (7)
C5	−0.1351 (5)	0.1970 (4)	0.3275 (2)	0.0238 (9)
C6	−0.0655 (5)	0.2583 (4)	0.2709 (2)	0.0255 (9)
C7	−0.0320 (5)	0.4080 (4)	0.2607 (2)	0.0252 (9)
H7	0.0155	0.4457	0.2226	0.030*
C8	−0.0676 (5)	0.5061 (4)	0.3065 (2)	0.0240 (9)
C9	−0.1364 (5)	0.4442 (4)	0.3654 (2)	0.0230 (8)
C10	−0.1673 (5)	0.2922 (4)	0.3740 (2)	0.0251 (9)
H10	−0.2114	0.2530	0.4125	0.030*
Cl11	−0.02174 (15)	0.14647 (11)	0.20952 (6)	0.0382 (3)
C12	−0.1769 (6)	0.5384 (4)	0.4175 (2)	0.0289 (9)
O13	−0.1611 (5)	0.6708 (3)	0.41192 (16)	0.0448 (9)
O14	−0.2343 (4)	0.4663 (3)	0.47002 (15)	0.0371 (8)
H14	−0.2540	0.5245	0.4967	0.056*
N15	−0.0351 (4)	0.6550 (3)	0.29613 (17)	0.0286 (8)
H15	−0.0548	0.7112	0.3268	0.034*
C16	0.0306 (6)	0.7251 (4)	0.2368 (2)	0.0309 (10)
H16A	0.1272	0.6971	0.2296	0.037*
H16B	0.0754	0.8354	0.2477	0.037*
C17	−0.0985 (6)	0.6825 (4)	0.1714 (2)	0.0321 (10)
O18	−0.2298 (4)	0.7371 (4)	0.16793 (17)	0.0455 (8)
C19	−0.3322 (7)	0.6860 (6)	0.1038 (3)	0.0531 (13)
H19	−0.4309	0.7066	0.0881	0.064*
C20	−0.2722 (8)	0.6033 (6)	0.0671 (3)	0.0553 (14)
H20	−0.3187	0.5569	0.0219	0.066*
C21	−0.1217 (7)	0.5993 (5)	0.1108 (3)	0.0496 (13)
H21	−0.0520	0.5482	0.0994	0.060*
C22	0.1070 (9)	−0.2451 (7)	−0.0202 (3)	0.0787 (19)
H22A	0.0922	−0.3460	−0.0084	0.118*
H22B	0.1309	−0.2361	−0.0663	0.118*
H22C	0.0024	−0.2273	−0.0181	0.118*
C23	0.2535 (8)	−0.1310 (6)	0.0292 (3)	0.0526 (14)
O24	0.3411 (6)	−0.1677 (4)	0.0749 (2)	0.0755 (12)
C25	0.2924 (8)	0.0340 (6)	0.0172 (3)	0.0582 (15)
H25A	0.1850	0.0519	0.0133	0.070*
H25B	0.3304	0.0494	−0.0269	0.070*
C26	0.4327 (7)	0.1567 (6)	0.0738 (2)	0.0496 (13)
H26A	0.5309	0.1263	0.0868	0.060*
H26B	0.4745	0.2541	0.0552	0.060*
C27	0.3581 (6)	0.1750 (5)	0.1376 (2)	0.0386 (11)
H27A	0.2905	0.0748	0.1494	0.046*
H27B	0.2812	0.2299	0.1277	0.046*
C28	0.5035 (6)	0.2621 (5)	0.1986 (2)	0.0410 (11)
H28A	0.5813	0.2076	0.2072	0.049*
H28B	0.5700	0.3620	0.1863	0.049*
N29	0.4410 (5)	0.2826 (4)	0.26303 (18)	0.0327 (8)
C30	0.4310 (6)	0.4238 (5)	0.2793 (2)	0.0359 (10)
N31	0.3889 (4)	0.4488 (3)	0.34216 (17)	0.0301 (8)
C32	0.3527 (5)	0.3335 (4)	0.3846 (2)	0.0272 (9)
C33	0.3623 (5)	0.1964 (4)	0.3670 (2)	0.0268 (9)
C34	0.4046 (5)	0.1593 (5)	0.3028 (2)	0.0317 (10)
O35	0.4088 (4)	0.0371 (3)	0.28192 (16)	0.0386 (7)
O36	0.4592 (5)	0.5218 (4)	0.23925 (17)	0.0520 (9)
C37	0.3884 (6)	0.5995 (4)	0.3644 (2)	0.0390 (11)
H37A	0.3566	0.5982	0.4092	0.059*
H37B	0.3059	0.6220	0.3316	0.059*
H37C	0.5024	0.6765	0.3670	0.059*
N38	0.3027 (5)	0.3392 (3)	0.44655 (17)	0.0292 (8)
C39	0.2823 (6)	0.2007 (4)	0.4666 (2)	0.0311 (10)
H39	0.2473	0.1698	0.5078	0.037*
N40	0.3176 (5)	0.1114 (3)	0.42096 (17)	0.0301 (8)
C41	0.3046 (6)	−0.0468 (4)	0.4270 (2)	0.0355 (10)
H41A	0.2801	−0.0741	0.4717	0.053*
H41B	0.4127	−0.0549	0.4217	0.053*
H41C	0.2125	−0.1148	0.3915	0.053*
O42	0.2316 (7)	0.5238 (6)	0.1180 (3)	0.0948 (15)
H42A	0.295 (9)	0.538 (8)	0.1651 (17)	0.114*
H42B	0.283 (9)	0.630 (4)	0.108 (4)	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0369 (7)	0.0187 (4)	0.0371 (6)	0.0142 (4)	0.0124 (5)	0.0077 (4)
N2	0.033 (2)	0.0248 (16)	0.051 (2)	0.0111 (15)	0.0120 (19)	−0.0038 (15)
O3	0.055 (2)	0.0289 (14)	0.0378 (18)	0.0192 (14)	0.0209 (16)	0.0147 (12)
O4	0.0414 (19)	0.0282 (14)	0.052 (2)	0.0215 (13)	0.0111 (16)	0.0105 (13)
C5	0.026 (2)	0.0162 (16)	0.030 (2)	0.0087 (15)	0.0059 (18)	0.0045 (15)
C6	0.025 (2)	0.0235 (18)	0.028 (2)	0.0115 (16)	0.0020 (18)	−0.0009 (15)
C7	0.027 (2)	0.0242 (18)	0.025 (2)	0.0091 (16)	0.0078 (19)	0.0051 (15)
C8	0.024 (2)	0.0183 (17)	0.028 (2)	0.0069 (15)	0.0026 (18)	0.0021 (15)
C9	0.025 (2)	0.0186 (17)	0.027 (2)	0.0100 (16)	0.0041 (18)	0.0039 (15)
C10	0.029 (2)	0.0251 (18)	0.025 (2)	0.0132 (17)	0.0091 (18)	0.0063 (15)
Cl11	0.0554 (8)	0.0304 (5)	0.0397 (7)	0.0228 (5)	0.0235 (6)	0.0048 (4)
C12	0.035 (3)	0.0263 (19)	0.026 (2)	0.0130 (17)	0.006 (2)	0.0005 (16)
O13	0.077 (2)	0.0268 (15)	0.044 (2)	0.0271 (15)	0.0287 (18)	0.0087 (13)
O14	0.060 (2)	0.0264 (14)	0.0335 (17)	0.0206 (14)	0.0221 (16)	0.0052 (12)
N15	0.042 (2)	0.0197 (15)	0.0270 (19)	0.0132 (15)	0.0118 (17)	0.0041 (13)
C16	0.041 (3)	0.0206 (18)	0.034 (3)	0.0116 (18)	0.012 (2)	0.0078 (16)
C17	0.040 (3)	0.0213 (19)	0.038 (3)	0.0114 (18)	0.014 (2)	0.0131 (17)
O18	0.050 (2)	0.0546 (19)	0.041 (2)	0.0297 (16)	0.0104 (17)	0.0076 (15)
C19	0.051 (4)	0.069 (3)	0.044 (3)	0.028 (3)	0.005 (3)	0.018 (3)
C20	0.068 (4)	0.056 (3)	0.038 (3)	0.025 (3)	−0.007 (3)	0.006 (2)
C21	0.070 (4)	0.047 (3)	0.042 (3)	0.036 (3)	0.008 (3)	−0.003 (2)
C22	0.090 (5)	0.075 (4)	0.054 (4)	0.014 (4)	0.010 (4)	−0.006 (3)
C23	0.063 (4)	0.049 (3)	0.059 (4)	0.029 (3)	0.026 (3)	0.010 (3)
O24	0.072 (3)	0.067 (2)	0.094 (3)	0.036 (2)	0.005 (3)	0.033 (2)
C25	0.080 (4)	0.060 (3)	0.045 (3)	0.035 (3)	0.020 (3)	0.008 (2)
C26	0.058 (4)	0.066 (3)	0.033 (3)	0.031 (3)	0.014 (3)	−0.001 (2)
C27	0.038 (3)	0.047 (3)	0.032 (3)	0.018 (2)	0.008 (2)	0.000 (2)
C28	0.036 (3)	0.054 (3)	0.032 (3)	0.014 (2)	0.013 (2)	0.004 (2)
N29	0.031 (2)	0.0363 (18)	0.027 (2)	0.0073 (16)	0.0095 (17)	0.0006 (15)
C30	0.035 (3)	0.037 (2)	0.029 (3)	0.0071 (19)	0.005 (2)	0.0029 (19)
N31	0.033 (2)	0.0231 (16)	0.029 (2)	0.0061 (14)	0.0030 (17)	0.0031 (14)
C32	0.025 (2)	0.0290 (19)	0.025 (2)	0.0083 (17)	0.0034 (19)	0.0000 (16)
C33	0.027 (2)	0.0291 (19)	0.024 (2)	0.0110 (17)	0.0048 (19)	0.0015 (16)
C34	0.022 (2)	0.041 (2)	0.031 (2)	0.0123 (18)	0.0011 (19)	−0.0052 (18)
O35	0.0400 (19)	0.0443 (17)	0.0363 (18)	0.0229 (14)	0.0074 (15)	−0.0073 (13)
O36	0.066 (3)	0.0460 (18)	0.038 (2)	0.0101 (17)	0.0163 (18)	0.0151 (15)
C37	0.052 (3)	0.025 (2)	0.041 (3)	0.015 (2)	0.010 (2)	0.0097 (18)
N38	0.038 (2)	0.0261 (16)	0.0227 (19)	0.0112 (15)	0.0068 (16)	0.0017 (13)
C39	0.037 (3)	0.027 (2)	0.027 (2)	0.0108 (18)	0.004 (2)	0.0007 (16)
N40	0.039 (2)	0.0243 (16)	0.0273 (19)	0.0135 (15)	0.0048 (17)	0.0015 (14)
C41	0.046 (3)	0.0252 (19)	0.037 (3)	0.0177 (19)	0.003 (2)	0.0027 (17)
O42	0.082 (4)	0.085 (3)	0.114 (4)	0.030 (3)	0.006 (3)	0.033 (3)

Geometric parameters (Å, º)

S1—O3	1.429 (3)	C23—O24	1.214 (7)
S1—O4	1.435 (3)	C23—C25	1.510 (7)
S1—N2	1.594 (4)	C25—C26	1.561 (7)
S1—C5	1.771 (3)	C25—H25A	0.9700
N2—H2A	1.0396	C25—H25B	0.9700
N2—H2B	1.0081	C26—C27	1.518 (6)
C5—C10	1.378 (5)	C26—H26A	0.9700
C5—C6	1.392 (5)	C26—H26B	0.9700
C6—C7	1.369 (5)	C27—C28	1.522 (6)
C6—Cl11	1.737 (4)	C27—H27A	0.9700
C7—C8	1.404 (5)	C27—H27B	0.9700
C7—H7	0.9300	C28—N29	1.479 (5)
C8—N15	1.363 (4)	C28—H28A	0.9700
C8—C9	1.431 (5)	C28—H28B	0.9700
C9—C10	1.386 (5)	N29—C30	1.393 (5)
C9—C12	1.486 (5)	N29—C34	1.401 (5)
C10—H10	0.9300	C30—O36	1.225 (5)
C12—O13	1.221 (4)	C30—N31	1.373 (5)
C12—O14	1.322 (5)	N31—C32	1.377 (5)
O14—H14	0.8200	N31—C37	1.472 (5)
N15—C16	1.455 (5)	C32—N38	1.357 (5)
N15—H15	0.8600	C32—C33	1.359 (5)
C16—C17	1.477 (6)	C33—N40	1.377 (5)
C16—H16A	0.9700	C33—C34	1.429 (5)
C16—H16B	0.9700	C34—O35	1.222 (5)
C17—C21	1.344 (6)	C37—H37A	0.9600
C17—O18	1.373 (5)	C37—H37B	0.9600
O18—C19	1.363 (6)	C37—H37C	0.9600
C19—C20	1.319 (7)	N38—C39	1.342 (5)
C19—H19	0.9300	C39—N40	1.343 (5)
C20—C21	1.425 (7)	C39—H39	0.9300
C20—H20	0.9300	N40—C41	1.470 (5)
C21—H21	0.9300	C41—H41A	0.9600
C22—C23	1.474 (8)	C41—H41B	0.9600
C22—H22A	0.9600	C41—H41C	0.9600
C22—H22B	0.9600	O42—H42A	0.97 (2)
C22—H22C	0.9600	O42—H42B	0.98 (2)
O3—S1—O4	119.19 (19)	C23—C25—C26	116.1 (5)
O3—S1—N2	108.55 (19)	C23—C25—H25A	108.3
O4—S1—N2	106.49 (18)	C26—C25—H25A	108.3
O3—S1—C5	105.33 (16)	C23—C25—H25B	108.3
O4—S1—C5	109.31 (17)	C26—C25—H25B	108.3
N2—S1—C5	107.48 (18)	H25A—C25—H25B	107.4
S1—N2—H2A	115.3	C27—C26—C25	111.0 (4)
S1—N2—H2B	105.7	C27—C26—H26A	109.4
H2A—N2—H2B	127.9	C25—C26—H26A	109.4
C10—C5—C6	118.1 (3)	C27—C26—H26B	109.4
C10—C5—S1	118.2 (3)	C25—C26—H26B	109.4
C6—C5—S1	123.7 (3)	H26A—C26—H26B	108.0
C7—C6—C5	121.3 (3)	C26—C27—C28	110.6 (4)
C7—C6—Cl11	117.5 (3)	C26—C27—H27A	109.5
C5—C6—Cl11	121.2 (3)	C28—C27—H27A	109.5
C6—C7—C8	121.6 (3)	C26—C27—H27B	109.5
C6—C7—H7	119.2	C28—C27—H27B	109.5
C8—C7—H7	119.2	H27A—C27—H27B	108.1
N15—C8—C7	121.6 (3)	N29—C28—C27	113.7 (4)
N15—C8—C9	121.2 (3)	N29—C28—H28A	108.8
C7—C8—C9	117.2 (3)	C27—C28—H28A	108.8
C10—C9—C8	119.4 (3)	N29—C28—H28B	108.8
C10—C9—C12	119.0 (3)	C27—C28—H28B	108.8
C8—C9—C12	121.7 (3)	H28A—C28—H28B	107.7
C5—C10—C9	122.4 (3)	C30—N29—C34	126.9 (3)
C5—C10—H10	118.8	C30—N29—C28	116.9 (3)
C9—C10—H10	118.8	C34—N29—C28	116.2 (3)
O13—C12—O14	122.6 (3)	O36—C30—N31	121.4 (4)
O13—C12—C9	122.9 (4)	O36—C30—N29	121.4 (4)
O14—C12—C9	114.5 (3)	N31—C30—N29	117.2 (3)
C12—O14—H14	109.5	C30—N31—C32	119.4 (3)
C8—N15—C16	124.4 (3)	C30—N31—C37	119.8 (3)
C8—N15—H15	117.8	C32—N31—C37	120.8 (3)
C16—N15—H15	117.8	N38—C32—C33	112.0 (3)
N15—C16—C17	115.1 (3)	N38—C32—N31	126.0 (3)
N15—C16—H16A	108.5	C33—C32—N31	122.0 (3)
C17—C16—H16A	108.5	C32—C33—N40	105.7 (3)
N15—C16—H16B	108.5	C32—C33—C34	122.8 (4)
C17—C16—H16B	108.5	N40—C33—C34	131.4 (3)
H16A—C16—H16B	107.5	O35—C34—N29	121.5 (4)
C21—C17—O18	108.2 (4)	O35—C34—C33	126.9 (4)
C21—C17—C16	135.1 (4)	N29—C34—C33	111.6 (3)
O18—C17—C16	116.7 (4)	N31—C37—H37A	109.5
C19—O18—C17	107.1 (4)	N31—C37—H37B	109.5
C20—C19—O18	110.8 (5)	H37A—C37—H37B	109.5
C20—C19—H19	124.6	N31—C37—H37C	109.5
O18—C19—H19	124.6	H37A—C37—H37C	109.5
C19—C20—C21	106.1 (5)	H37B—C37—H37C	109.5
C19—C20—H20	126.9	C39—N38—C32	103.2 (3)
C21—C20—H20	126.9	N38—C39—N40	113.1 (4)
C17—C21—C20	107.8 (4)	N38—C39—H39	123.4
C17—C21—H21	126.1	N40—C39—H39	123.4
C20—C21—H21	126.1	C39—N40—C33	106.0 (3)
C23—C22—H22A	109.5	C39—N40—C41	126.4 (3)
C23—C22—H22B	109.5	C33—N40—C41	127.5 (3)
H22A—C22—H22B	109.5	N40—C41—H41A	109.5
C23—C22—H22C	109.5	N40—C41—H41B	109.5
H22A—C22—H22C	109.5	H41A—C41—H41B	109.5
H22B—C22—H22C	109.5	N40—C41—H41C	109.5
O24—C23—C22	122.2 (5)	H41A—C41—H41C	109.5
O24—C23—C25	122.2 (5)	H41B—C41—H41C	109.5
C22—C23—C25	115.5 (5)	H42A—O42—H42B	97 (6)
O3—S1—C5—C10	−0.1 (4)	C22—C23—C25—C26	173.2 (5)
O4—S1—C5—C10	−129.3 (3)	C23—C25—C26—C27	−76.9 (6)
N2—S1—C5—C10	115.5 (3)	C25—C26—C27—C28	165.5 (4)
O3—S1—C5—C6	−178.3 (4)	C26—C27—C28—N29	−179.2 (4)
O4—S1—C5—C6	52.5 (4)	C27—C28—N29—C30	−99.6 (5)
N2—S1—C5—C6	−62.7 (4)	C27—C28—N29—C34	82.8 (5)
C10—C5—C6—C7	−0.9 (6)	C34—N29—C30—O36	−177.0 (4)
S1—C5—C6—C7	177.3 (3)	C28—N29—C30—O36	5.7 (6)
C10—C5—C6—Cl11	−179.7 (3)	C34—N29—C30—N31	3.3 (6)
S1—C5—C6—Cl11	−1.5 (5)	C28—N29—C30—N31	−174.0 (4)
C5—C6—C7—C8	−0.6 (6)	O36—C30—N31—C32	177.9 (4)
Cl11—C6—C7—C8	178.2 (3)	N29—C30—N31—C32	−2.4 (6)
C6—C7—C8—N15	−179.6 (4)	O36—C30—N31—C37	−4.0 (7)
C6—C7—C8—C9	1.6 (6)	N29—C30—N31—C37	175.7 (4)
N15—C8—C9—C10	−179.9 (4)	C30—N31—C32—N38	−177.2 (4)
C7—C8—C9—C10	−1.1 (6)	C37—N31—C32—N38	4.7 (6)
N15—C8—C9—C12	0.5 (6)	C30—N31—C32—C33	2.0 (6)
C7—C8—C9—C12	179.3 (4)	C37—N31—C32—C33	−176.1 (4)
C6—C5—C10—C9	1.4 (6)	N38—C32—C33—N40	−0.6 (5)
S1—C5—C10—C9	−176.9 (3)	N31—C32—C33—N40	−179.9 (4)
C8—C9—C10—C5	−0.4 (6)	N38—C32—C33—C34	177.2 (4)
C12—C9—C10—C5	179.2 (4)	N31—C32—C33—C34	−2.2 (6)
C10—C9—C12—O13	−176.5 (4)	C30—N29—C34—O35	176.1 (4)
C8—C9—C12—O13	3.1 (7)	C28—N29—C34—O35	−6.6 (6)
C10—C9—C12—O14	2.5 (6)	C30—N29—C34—C33	−3.2 (6)
C8—C9—C12—O14	−177.9 (4)	C28—N29—C34—C33	174.1 (4)
C7—C8—N15—C16	2.9 (6)	C32—C33—C34—O35	−176.7 (4)
C9—C8—N15—C16	−178.4 (4)	N40—C33—C34—O35	0.3 (8)
C8—N15—C16—C17	75.2 (5)	C32—C33—C34—N29	2.5 (6)
N15—C16—C17—C21	−110.9 (5)	N40—C33—C34—N29	179.6 (4)
N15—C16—C17—O18	69.2 (4)	C33—C32—N38—C39	0.1 (5)
C21—C17—O18—C19	−0.3 (5)	N31—C32—N38—C39	179.4 (4)
C16—C17—O18—C19	179.6 (3)	C32—N38—C39—N40	0.4 (5)
C17—O18—C19—C20	−0.2 (5)	N38—C39—N40—C33	−0.7 (5)
O18—C19—C20—C21	0.7 (6)	N38—C39—N40—C41	−178.8 (4)
O18—C17—C21—C20	0.7 (5)	C32—C33—N40—C39	0.7 (5)
C16—C17—C21—C20	−179.1 (4)	C34—C33—N40—C39	−176.7 (4)
C19—C20—C21—C17	−0.9 (6)	C32—C33—N40—C41	178.8 (4)
O24—C23—C25—C26	−9.5 (8)	C34—C33—N40—C41	1.3 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H15···O13	0.86	2.01	2.681 (5)	134
N15—H15···O4^i	0.86	2.33	3.001 (4)	136
N2—H2A···O35^ii	1.04	1.86	2.849 (6)	158
N2—H2B···O18^iii	1.01	2.13	3.071 (6)	155
O14—H14···N38^iv	0.82	1.86	2.683 (5)	177
C39—H39···O13^iv	0.93	2.50	3.104 (6)	123
C39—H39···O3^v	0.93	2.36	3.170 (5)	146
O42—H42A···O36	0.97	1.90	2.815 (7)	158
O42—H42B···O24^i	0.98	1.96	2.929 (7)	168

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

(III) 4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid–3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione– acetone (1/1/1)

Crystal data

C12H11ClN2O5S·C13H18N4O3·C2H6O	Z = 2
Mr = 667.14	F(000) = 700
Triclinic, P1	Dx = 1.414 Mg m^−3
Hall symbol: -P 1	Melting point: 432 K
a = 9.3099 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5317 (3) Å	Cell parameters from 13851 reflections
c = 19.2653 (7) Å	θ = 1.0–27.5°
α = 99.733 (2)°	µ = 0.25 mm^−1
β = 96.057 (2)°	T = 190 K
γ = 109.197 (3)°	Plate, colourless
V = 1567.27 (9) Å^3	0.4 × 0.2 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	4277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 27.4°, θmin = 3.3°
CCD scans	h = −12→11
10665 measured reflections	k = −12→12
7045 independent reflections	l = −22→24

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.8394P] where P = (Fo^2 + 2Fc^2)/3
7045 reflections	(Δ/σ)max = 0.001
411 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−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	0.05003 (8)	0.37698 (9)	0.29152 (4)	0.02774 (19)
N2	0.2274 (3)	0.3888 (3)	0.29851 (14)	0.0339 (6)
H2A	0.2925	0.4801	0.3312	0.041*
H2B	0.2523	0.3761	0.2527	0.041*
O3	0.0155 (2)	0.3922 (2)	0.36296 (11)	0.0358 (5)
O4	−0.0395 (2)	0.2424 (2)	0.23874 (12)	0.0356 (5)
C5	0.0350 (3)	0.5386 (3)	0.26237 (15)	0.0229 (6)
C6	0.0538 (3)	0.5664 (3)	0.19390 (15)	0.0258 (6)
C7	0.0477 (3)	0.6964 (3)	0.17531 (16)	0.0262 (6)
H7	0.0597	0.7099	0.1293	0.031*
C8	0.0235 (3)	0.8111 (3)	0.22457 (15)	0.0248 (6)
C9	−0.0061 (3)	0.7791 (3)	0.29285 (15)	0.0221 (6)
C10	0.0031 (3)	0.6457 (3)	0.30968 (15)	0.0245 (6)
H10	−0.0130	0.6279	0.3547	0.029*
Cl11	0.08804 (9)	0.43489 (9)	0.12970 (4)	0.0379 (2)
C12	−0.0491 (3)	0.8839 (3)	0.34507 (15)	0.0239 (6)
O13	−0.0433 (2)	1.0103 (2)	0.33849 (11)	0.0359 (5)
O14	−0.0977 (2)	0.8265 (2)	0.40027 (11)	0.0326 (5)
H14	−0.1198	0.8893	0.4274	0.049*
N15	0.0271 (3)	0.9440 (3)	0.20814 (13)	0.0278 (6)
H15A	0.0173	1.0198	0.2483	0.033*
C16	0.0656 (3)	0.9890 (4)	0.14170 (16)	0.0298 (7)
H16A	0.1400	0.9452	0.1257	0.036*
H16B	0.1148	1.0989	0.1514	0.036*
C17	−0.0691 (3)	0.9419 (4)	0.08293 (16)	0.0311 (7)
O18	−0.1110 (3)	0.8101 (3)	0.03355 (14)	0.0534 (7)
C19	−0.2360 (4)	0.8058 (5)	−0.01363 (19)	0.0462 (9)
H19	−0.2870	0.7290	−0.0539	0.055*
C20	−0.2713 (4)	0.9263 (4)	0.0072 (2)	0.0481 (9)
H20	−0.3502	0.9508	−0.0155	0.058*
C21	−0.1664 (4)	1.0124 (4)	0.07078 (19)	0.0414 (9)
H21	−0.1664	1.1020	0.0988	0.050*
C22	0.3265 (5)	0.6281 (5)	0.0011 (2)	0.0581 (11)
H22A	0.2567	0.6662	−0.0232	0.087*
H22B	0.2709	0.5273	0.0066	0.087*
H22C	0.4061	0.6252	−0.0264	0.087*
C23	0.3985 (4)	0.7313 (4)	0.07388 (18)	0.0409 (8)
O24	0.3692 (3)	0.8451 (3)	0.09201 (14)	0.0559 (7)
C25	0.5062 (4)	0.6865 (4)	0.12106 (17)	0.0373 (8)
H25A	0.5886	0.6776	0.0958	0.045*
H25B	0.4503	0.5865	0.1289	0.045*
C26	0.5782 (3)	0.7928 (4)	0.19310 (16)	0.0352 (8)
H26A	0.6280	0.8947	0.1858	0.042*
H26B	0.6577	0.7617	0.2154	0.042*
C27	0.4648 (3)	0.7983 (4)	0.24421 (16)	0.0335 (7)
H27A	0.3965	0.8477	0.2270	0.040*
H27B	0.4022	0.6956	0.2461	0.040*
C28	0.5515 (3)	0.8851 (4)	0.31846 (16)	0.0339 (7)
H28A	0.6146	0.8313	0.3362	0.041*
H28B	0.6203	0.9845	0.3152	0.041*
N29	0.4499 (3)	0.9058 (3)	0.37071 (13)	0.0304 (6)
C30	0.4189 (3)	1.0413 (4)	0.37893 (16)	0.0316 (7)
N31	0.3307 (3)	1.0653 (3)	0.43025 (13)	0.0280 (6)
C32	0.2790 (3)	0.9577 (3)	0.46971 (15)	0.0272 (7)
C33	0.3084 (3)	0.8251 (4)	0.45923 (15)	0.0286 (7)
C34	0.3971 (3)	0.7890 (4)	0.40776 (16)	0.0281 (7)
O35	0.4290 (2)	0.6727 (3)	0.39570 (11)	0.0361 (5)
O36	0.4706 (3)	1.1351 (3)	0.34384 (13)	0.0457 (6)
C37	0.2959 (4)	1.2062 (4)	0.44214 (18)	0.0385 (8)
H37A	0.1885	1.1823	0.4453	0.058*
H37B	0.3185	1.2556	0.4030	0.058*
H37C	0.3578	1.2728	0.4859	0.058*
N38	0.1950 (3)	0.9665 (3)	0.52287 (13)	0.0285 (6)
C39	0.1730 (3)	0.8358 (4)	0.54425 (16)	0.0289 (7)
H39	0.1183	0.8096	0.5807	0.035*
N40	0.2373 (3)	0.7465 (3)	0.50821 (13)	0.0292 (6)
C41	0.2379 (4)	0.5991 (4)	0.52044 (18)	0.0371 (8)
H41A	0.1926	0.5229	0.4771	0.056*
H41B	0.1792	0.5719	0.5573	0.056*
H41C	0.3422	0.6059	0.5349	0.056*
O42	0.3995 (3)	0.3296 (3)	0.18606 (14)	0.0573 (7)
C43	0.5221 (4)	0.3295 (4)	0.21450 (18)	0.0377 (8)
C44	0.6080 (4)	0.4392 (5)	0.2821 (2)	0.0550 (10)
H44A	0.5464	0.4961	0.2996	0.083*
H44B	0.7029	0.5075	0.2735	0.083*
H44C	0.6303	0.3848	0.3170	0.083*
C45	0.5897 (5)	0.2184 (6)	0.1823 (2)	0.0659 (12)
H45A	0.5166	0.1462	0.1428	0.099*
H45B	0.6142	0.1658	0.2175	0.099*
H45C	0.6820	0.2711	0.1657	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0324 (4)	0.0238 (4)	0.0314 (4)	0.0130 (3)	0.0091 (3)	0.0094 (3)
N2	0.0347 (14)	0.0339 (15)	0.0378 (16)	0.0184 (12)	0.0048 (11)	0.0090 (13)
O3	0.0512 (13)	0.0325 (13)	0.0343 (13)	0.0205 (10)	0.0189 (10)	0.0162 (10)
O4	0.0403 (12)	0.0231 (12)	0.0416 (14)	0.0103 (9)	0.0062 (10)	0.0047 (10)
C5	0.0252 (14)	0.0223 (15)	0.0239 (15)	0.0108 (12)	0.0052 (11)	0.0069 (12)
C6	0.0241 (14)	0.0283 (17)	0.0272 (16)	0.0125 (12)	0.0068 (12)	0.0035 (13)
C7	0.0314 (15)	0.0281 (17)	0.0240 (16)	0.0139 (13)	0.0090 (12)	0.0088 (13)
C8	0.0215 (14)	0.0234 (16)	0.0301 (17)	0.0076 (12)	0.0042 (11)	0.0087 (13)
C9	0.0223 (14)	0.0220 (15)	0.0222 (15)	0.0084 (11)	0.0042 (11)	0.0042 (12)
C10	0.0229 (14)	0.0271 (16)	0.0232 (15)	0.0081 (12)	0.0044 (11)	0.0064 (13)
Cl11	0.0551 (5)	0.0344 (5)	0.0333 (5)	0.0252 (4)	0.0179 (4)	0.0063 (4)
C12	0.0219 (14)	0.0262 (17)	0.0233 (16)	0.0079 (12)	0.0029 (11)	0.0065 (13)
O13	0.0517 (13)	0.0289 (13)	0.0355 (13)	0.0206 (10)	0.0177 (10)	0.0101 (10)
O14	0.0456 (12)	0.0338 (12)	0.0272 (12)	0.0212 (10)	0.0155 (9)	0.0092 (10)
N15	0.0404 (14)	0.0239 (14)	0.0231 (13)	0.0142 (11)	0.0094 (11)	0.0076 (11)
C16	0.0363 (17)	0.0275 (17)	0.0294 (17)	0.0124 (13)	0.0104 (13)	0.0106 (14)
C17	0.0380 (17)	0.0283 (17)	0.0266 (17)	0.0072 (14)	0.0115 (13)	0.0104 (14)
O18	0.0581 (16)	0.0480 (16)	0.0522 (17)	0.0241 (13)	0.0026 (13)	−0.0012 (14)
C19	0.0398 (19)	0.058 (3)	0.032 (2)	0.0110 (18)	0.0011 (15)	0.0025 (18)
C20	0.0384 (19)	0.049 (2)	0.063 (3)	0.0165 (17)	0.0069 (17)	0.029 (2)
C21	0.0369 (18)	0.0311 (19)	0.051 (2)	0.0172 (15)	−0.0016 (16)	−0.0093 (17)
C22	0.062 (2)	0.068 (3)	0.035 (2)	0.013 (2)	0.0039 (17)	0.010 (2)
C23	0.0432 (19)	0.051 (2)	0.0328 (19)	0.0183 (17)	0.0119 (15)	0.0143 (17)
O24	0.0751 (18)	0.0628 (19)	0.0452 (16)	0.0427 (15)	0.0111 (13)	0.0153 (14)
C25	0.0469 (19)	0.037 (2)	0.0329 (19)	0.0186 (16)	0.0154 (15)	0.0076 (16)
C26	0.0330 (17)	0.046 (2)	0.0308 (18)	0.0165 (15)	0.0125 (13)	0.0099 (16)
C27	0.0283 (16)	0.044 (2)	0.0277 (17)	0.0111 (14)	0.0094 (13)	0.0059 (15)
C28	0.0280 (16)	0.044 (2)	0.0290 (17)	0.0119 (14)	0.0093 (13)	0.0061 (15)
N29	0.0294 (13)	0.0375 (16)	0.0255 (14)	0.0120 (11)	0.0094 (10)	0.0070 (12)
C30	0.0334 (17)	0.0347 (19)	0.0268 (17)	0.0113 (14)	0.0052 (13)	0.0084 (15)
N31	0.0306 (13)	0.0293 (14)	0.0257 (13)	0.0110 (11)	0.0068 (10)	0.0078 (11)
C32	0.0295 (15)	0.0314 (17)	0.0200 (15)	0.0113 (13)	0.0023 (12)	0.0038 (13)
C33	0.0297 (16)	0.0332 (18)	0.0241 (16)	0.0128 (13)	0.0063 (12)	0.0050 (14)
C34	0.0242 (15)	0.0333 (18)	0.0242 (16)	0.0097 (13)	0.0010 (12)	0.0023 (14)
O35	0.0391 (12)	0.0400 (14)	0.0341 (13)	0.0206 (11)	0.0109 (10)	0.0051 (11)
O36	0.0550 (14)	0.0444 (15)	0.0457 (15)	0.0181 (12)	0.0233 (12)	0.0211 (12)
C37	0.0474 (19)	0.036 (2)	0.0378 (19)	0.0206 (16)	0.0094 (15)	0.0113 (16)
N38	0.0300 (13)	0.0343 (15)	0.0235 (13)	0.0135 (11)	0.0073 (10)	0.0064 (11)
C39	0.0294 (15)	0.0314 (18)	0.0251 (16)	0.0093 (13)	0.0099 (12)	0.0039 (14)
N40	0.0335 (13)	0.0311 (15)	0.0257 (14)	0.0133 (11)	0.0088 (11)	0.0074 (11)
C41	0.0476 (19)	0.0320 (19)	0.0365 (19)	0.0152 (15)	0.0168 (15)	0.0119 (15)
O42	0.0433 (14)	0.083 (2)	0.0483 (16)	0.0347 (14)	−0.0020 (12)	0.0010 (14)
C43	0.0338 (18)	0.044 (2)	0.041 (2)	0.0148 (15)	0.0100 (15)	0.0183 (17)
C44	0.039 (2)	0.054 (2)	0.062 (3)	0.0069 (18)	0.0005 (17)	0.008 (2)
C45	0.063 (3)	0.084 (3)	0.061 (3)	0.044 (2)	0.006 (2)	0.007 (2)

Geometric parameters (Å, º)

S1—O4	1.432 (2)	C25—H25B	0.9700
S1—O3	1.440 (2)	C26—C27	1.525 (4)
S1—N2	1.607 (2)	C26—H26A	0.9700
S1—C5	1.768 (3)	C26—H26B	0.9700
N2—H2A	0.9534	C27—C28	1.516 (4)
N2—H2B	0.9333	C27—H27A	0.9700
C5—C10	1.379 (4)	C27—H27B	0.9700
C5—C6	1.406 (4)	C28—N29	1.484 (3)
C6—C7	1.363 (4)	C28—H28A	0.9700
C6—Cl11	1.739 (3)	C28—H28B	0.9700
C7—C8	1.416 (4)	N29—C30	1.400 (4)
C7—H7	0.9300	N29—C34	1.406 (4)
C8—N15	1.348 (4)	C30—O36	1.216 (4)
C8—C9	1.434 (4)	C30—N31	1.387 (4)
C9—C10	1.391 (4)	N31—C32	1.371 (4)
C9—C12	1.476 (4)	N31—C37	1.470 (4)
C10—H10	0.9300	C32—N38	1.360 (4)
C12—O13	1.217 (3)	C32—C33	1.365 (4)
C12—O14	1.330 (3)	C33—N40	1.391 (4)
O14—H14	0.8200	C33—C34	1.424 (4)
N15—C16	1.460 (4)	C34—O35	1.230 (4)
N15—H15A	0.9990	C37—H37A	0.9600
C16—C17	1.488 (4)	C37—H37B	0.9600
C16—H16A	0.9700	C37—H37C	0.9600
C16—H16B	0.9700	N38—C39	1.336 (4)
C17—C21	1.317 (4)	C39—N40	1.337 (4)
C17—O18	1.353 (4)	C39—H39	0.9300
O18—C19	1.384 (4)	N40—C41	1.465 (4)
C19—C20	1.307 (5)	C41—H41A	0.9600
C19—H19	0.9300	C41—H41B	0.9600
C20—C21	1.417 (5)	C41—H41C	0.9600
C20—H20	0.9300	O42—C43	1.214 (4)
C21—H21	0.9300	C43—C44	1.482 (5)
C22—C23	1.512 (5)	C43—C45	1.484 (5)
C22—H22A	0.9600	C44—H44A	0.9600
C22—H22B	0.9600	C44—H44B	0.9600
C22—H22C	0.9600	C44—H44C	0.9600
C23—O24	1.208 (4)	C45—H45A	0.9600
C23—C25	1.495 (5)	C45—H45B	0.9600
C25—C26	1.511 (4)	C45—H45C	0.9600
C25—H25A	0.9700
O4—S1—O3	119.12 (13)	C25—C26—H26A	108.6
O4—S1—N2	107.52 (14)	C27—C26—H26A	108.6
O3—S1—N2	106.58 (14)	C25—C26—H26B	108.6
O4—S1—C5	109.54 (13)	C27—C26—H26B	108.6
O3—S1—C5	105.44 (13)	H26A—C26—H26B	107.6
N2—S1—C5	108.21 (13)	C28—C27—C26	110.2 (2)
S1—N2—H2A	110.6	C28—C27—H27A	109.6
S1—N2—H2B	108.5	C26—C27—H27A	109.6
H2A—N2—H2B	115.3	C28—C27—H27B	109.6
C10—C5—C6	117.3 (3)	C26—C27—H27B	109.6
C10—C5—S1	118.3 (2)	H27A—C27—H27B	108.1
C6—C5—S1	124.5 (2)	N29—C28—C27	113.9 (2)
C7—C6—C5	122.0 (3)	N29—C28—H28A	108.8
C7—C6—Cl11	117.5 (2)	C27—C28—H28A	108.8
C5—C6—Cl11	120.5 (2)	N29—C28—H28B	108.8
C6—C7—C8	121.4 (3)	C27—C28—H28B	108.8
C6—C7—H7	119.3	H28A—C28—H28B	107.7
C8—C7—H7	119.3	C30—N29—C34	126.7 (2)
N15—C8—C7	121.8 (3)	C30—N29—C28	116.5 (3)
N15—C8—C9	121.4 (3)	C34—N29—C28	116.7 (3)
C7—C8—C9	116.9 (3)	O36—C30—N31	121.7 (3)
C10—C9—C8	119.5 (3)	O36—C30—N29	121.3 (3)
C10—C9—C12	119.4 (3)	N31—C30—N29	117.0 (3)
C8—C9—C12	121.1 (3)	C32—N31—C30	119.3 (3)
C5—C10—C9	122.8 (3)	C32—N31—C37	121.1 (2)
C5—C10—H10	118.6	C30—N31—C37	119.6 (3)
C9—C10—H10	118.6	N38—C32—C33	111.6 (3)
O13—C12—O14	122.5 (3)	N38—C32—N31	126.1 (3)
O13—C12—C9	123.8 (3)	C33—C32—N31	122.2 (3)
O14—C12—C9	113.7 (2)	C32—C33—N40	105.3 (2)
C12—O14—H14	109.5	C32—C33—C34	123.0 (3)
C8—N15—C16	124.7 (2)	N40—C33—C34	131.7 (3)
C8—N15—H15A	114.8	O35—C34—N29	121.7 (3)
C16—N15—H15A	119.9	O35—C34—C33	126.6 (3)
N15—C16—C17	114.3 (2)	N29—C34—C33	111.7 (3)
N15—C16—H16A	108.7	N31—C37—H37A	109.5
C17—C16—H16A	108.7	N31—C37—H37B	109.5
N15—C16—H16B	108.7	H37A—C37—H37B	109.5
C17—C16—H16B	108.7	N31—C37—H37C	109.5
H16A—C16—H16B	107.6	H37A—C37—H37C	109.5
C21—C17—O18	109.6 (3)	H37B—C37—H37C	109.5
C21—C17—C16	128.3 (3)	C39—N38—C32	103.6 (2)
O18—C17—C16	122.0 (3)	N38—C39—N40	113.5 (2)
C17—O18—C19	106.4 (3)	N38—C39—H39	123.3
C20—C19—O18	109.5 (3)	N40—C39—H39	123.3
C20—C19—H19	125.3	C39—N40—C33	105.9 (2)
O18—C19—H19	125.3	C39—N40—C41	126.6 (2)
C19—C20—C21	107.0 (3)	C33—N40—C41	127.4 (2)
C19—C20—H20	126.5	N40—C41—H41A	109.5
C21—C20—H20	126.5	N40—C41—H41B	109.5
C17—C21—C20	107.3 (3)	H41A—C41—H41B	109.5
C17—C21—H21	126.3	N40—C41—H41C	109.5
C20—C21—H21	126.3	H41A—C41—H41C	109.5
C23—C22—H22A	109.5	H41B—C41—H41C	109.5
C23—C22—H22B	109.5	O42—C43—C44	121.3 (3)
H22A—C22—H22B	109.5	O42—C43—C45	120.5 (3)
C23—C22—H22C	109.5	C44—C43—C45	118.3 (3)
H22A—C22—H22C	109.5	C43—C44—H44A	109.5
H22B—C22—H22C	109.5	C43—C44—H44B	109.5
O24—C23—C25	122.4 (3)	H44A—C44—H44B	109.5
O24—C23—C22	120.4 (3)	C43—C44—H44C	109.5
C25—C23—C22	117.2 (3)	H44A—C44—H44C	109.5
C23—C25—C26	116.1 (3)	H44B—C44—H44C	109.5
C23—C25—H25A	108.3	C43—C45—H45A	109.5
C26—C25—H25A	108.3	C43—C45—H45B	109.5
C23—C25—H25B	108.3	H45A—C45—H45B	109.5
C26—C25—H25B	108.3	C43—C45—H45C	109.5
H25A—C25—H25B	107.4	H45A—C45—H45C	109.5
C25—C26—C27	114.5 (3)	H45B—C45—H45C	109.5
O4—S1—C5—C10	132.1 (2)	C22—C23—C25—C26	179.2 (3)
O3—S1—C5—C10	2.8 (3)	C23—C25—C26—C27	67.7 (4)
N2—S1—C5—C10	−111.0 (2)	C25—C26—C27—C28	169.9 (3)
O4—S1—C5—C6	−48.0 (3)	C26—C27—C28—N29	175.8 (3)
O3—S1—C5—C6	−177.3 (2)	C27—C28—N29—C30	−93.6 (3)
N2—S1—C5—C6	68.9 (3)	C27—C28—N29—C34	87.6 (3)
C10—C5—C6—C7	2.8 (4)	C34—N29—C30—O36	−179.9 (3)
S1—C5—C6—C7	−177.0 (2)	C28—N29—C30—O36	1.4 (4)
C10—C5—C6—Cl11	−177.9 (2)	C34—N29—C30—N31	1.9 (4)
S1—C5—C6—Cl11	2.2 (4)	C28—N29—C30—N31	−176.8 (2)
C5—C6—C7—C8	0.6 (4)	O36—C30—N31—C32	−178.2 (3)
Cl11—C6—C7—C8	−178.7 (2)	N29—C30—N31—C32	0.0 (4)
C6—C7—C8—N15	175.7 (3)	O36—C30—N31—C37	1.0 (4)
C6—C7—C8—C9	−4.7 (4)	N29—C30—N31—C37	179.2 (3)
N15—C8—C9—C10	−175.0 (2)	C30—N31—C32—N38	178.3 (3)
C7—C8—C9—C10	5.4 (4)	C37—N31—C32—N38	−0.9 (4)
N15—C8—C9—C12	6.2 (4)	C30—N31—C32—C33	−1.5 (4)
C7—C8—C9—C12	−173.5 (2)	C37—N31—C32—C33	179.3 (3)
C6—C5—C10—C9	−2.0 (4)	N38—C32—C33—N40	0.6 (3)
S1—C5—C10—C9	177.9 (2)	N31—C32—C33—N40	−179.6 (3)
C8—C9—C10—C5	−2.1 (4)	N38—C32—C33—C34	−178.6 (3)
C12—C9—C10—C5	176.7 (3)	N31—C32—C33—C34	1.2 (4)
C10—C9—C12—O13	171.5 (3)	C30—N29—C34—O35	178.8 (3)
C8—C9—C12—O13	−9.7 (4)	C28—N29—C34—O35	−2.5 (4)
C10—C9—C12—O14	−9.5 (4)	C30—N29—C34—C33	−2.1 (4)
C8—C9—C12—O14	169.3 (2)	C28—N29—C34—C33	176.6 (2)
C7—C8—N15—C16	−4.3 (4)	C32—C33—C34—O35	179.5 (3)
C9—C8—N15—C16	176.1 (3)	N40—C33—C34—O35	0.6 (5)
C8—N15—C16—C17	89.5 (3)	C32—C33—C34—N29	0.5 (4)
N15—C16—C17—C21	84.6 (4)	N40—C33—C34—N29	−178.5 (3)
N15—C16—C17—O18	−93.4 (3)	C33—C32—N38—C39	−0.4 (3)
C21—C17—O18—C19	3.7 (4)	N31—C32—N38—C39	179.8 (3)
C16—C17—O18—C19	−178.0 (3)	C32—N38—C39—N40	0.0 (3)
C17—O18—C19—C20	−1.8 (4)	N38—C39—N40—C33	0.4 (3)
O18—C19—C20—C21	−0.6 (4)	N38—C39—N40—C41	177.9 (3)
O18—C17—C21—C20	−4.0 (4)	C32—C33—N40—C39	−0.6 (3)
C16—C17—C21—C20	177.8 (3)	C34—C33—N40—C39	178.5 (3)
C19—C20—C21—C17	2.8 (4)	C32—C33—N40—C41	−178.1 (3)
O24—C23—C25—C26	−0.5 (5)	C34—C33—N40—C41	1.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H15A···O13	1.00	1.89	2.687 (3)	135
N15—H15A···O4^i	1.00	2.38	3.081 (4)	127
N2—H2A···O35	0.95	1.97	2.925 (3)	178
O14—H14···N38^ii	0.82	1.90	2.716 (4)	171
C39—H39···O13^ii	0.93	2.44	3.055 (4)	123
C39—H39···O3^iii	0.93	2.42	3.235 (4)	147
N2—H2B···O42	0.93	2.07	2.914 (4)	149

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