Hirshfeld surface analysis of sulfameter (polymorph III), sulfameter dioxane monosolvate and sulfameter tetra­hydro­furan monosolvate, all at 296 K

The ability of the anti­bacterial agent sulfameter (SMT) to form solvates is investigated. The X-ray crystal structures of sulfameter solvates have been determined to be conformational polymorphs. Both 1,4-dioxane and tetra­hydro­furan form solvates with sulfameter in a 1:1 molar ratio. 4-Amino-N-(5-meth­oxypyrimidin-2-yl)benzene­sulfonamide (polymorph III), C₁₁H₁₂N₄O₃S, (1), has two mol­ecules of sulfameter in the asymmetric unit cell. 4-Amino-N-(5-meth­oxypyrimidin-2-yl)benzene­sulfonamide 1,4-dioxane monosolvate, C₁₁H₁₂N₄O₃S·C₄H₈O₂, (2), and 4-amino-N-(5-meth­oxypyrimidin-2-yl)benzene­sulfon­amide tetra­hydro­furan monosolvate, C₁₁H₁₂N₄O₃S·C₄H₈O, (3), crystallize in the imide form. Hirshfeld surface analyses and fingerprint analyses were performed to study the nature of the inter­actions and their qu­anti­tative contributions towards the crystal packing. Finally, Hirshfeld surfaces, fingerprint plots and structural overlays were employed for a comparison of the two independent mol­ecules in the asymmetric unit of (1), and also for a comparison of (2) and (3) in the monoclinic crystal system. A three-dimensional hydrogen-bonding network exists in all three structures, involving one of the sulfone O atoms and the aniline N atom. All three structures are stabilized by strong inter­molecular N—H...N inter­actions. The tetra­hydro­furan solvent molecule also takes part in forming significant inter­molecular C—H...O inter­actions in the crystal structure of (3), contributing to the stability of the crystal packing.

S1. Introduction

Pharmaceutical solvates, crystalline solids of active pharmaceutical ingredients (APIs) incorporating one or more solvent molecules in their crystal structure, have received particular attention as the presence of a particular solvent in the crystal structure can impart characteristic physiochemical properties to the APIs (Byrn et al., 1999; Lee et al., 2011). Therefore, solvates are of significant importance in drug development. Sulfonamides have been widely recognized for their wide variety of pharmacological activities, such as anti­bacterial, anti­tumour, anti­carbonic anhydrase, hypoglycaemic, anti­thyroid and protease-inhibitory activity. The clinically useful sulfonamides are derived from sulfanilamide, which is similar to para-amino­benzoic acid, a factor required by bacteria for folic acid synthesis (Wolff, 1996). Sulfameter is a member of the sulfonamide class of pharmaceuticals known for its anti­bacterial, anti­thyroid and anti­diabetic properties. It was the first synthetic anti­biotic leprostatic agent to treat urinary tract infections [Reference?].

Our initial inter­est in sulfameter is prompted by its ability to form conformational polymorphs, molecules that adopt different molecular conformations in different crystalline forms. The pharmaceutical industry is particularly inter­ested in polymorphism because it can result in seemingly identical compounds having different pharmacological activity and/or bioavailability due to varying levels of thermodynamic stability, equilibrium solubilities and rates of dissolution. The X-ray crystal structures of the sulfameter polymorphs numbered I and II have been reported by Giuseppetti et al. (1977) and Caira (1994), respectively.

In an effort to crystallize sulfameter, (1), in its different polymorphic forms, we have prepared two crystalline sulfameter solvates: sulfameter dioxane solvate, (2), and sulfameter tetra­hydro­furan solvate, (3). The work presented here forms part of a wider investigation that couples parallel crystallization searches (Caira & Mohamed, 1993; Pratt et al., 2011) with crystal structure prediction methodology to investigate the basic science underlying the solid-state diversity in sulfameter solvate. We report here the Hirshfeld surface analysis and the crystal structures of these two sulfameter solvates along with the crystal structure of sulfameter (polymorph III) determined at 296 K. The conformations of the sulfameter molecules in these solvate structures provide additional examples of conformational polymorphism.

S2. Experimental

S2.1. Synthesis and crystallization

All the sulfameter crystals were prepared by slow evaporation from a saturated solution of sulfameter and the relevant solvent [butanol for (1), dioxane for (2) and tetra­hydro­furan for (3)]. The mixtures were left to stand at room temperature for a few days after mixing. Single crystals were collected after evaporation of the mixtures and were air-dried.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically, with N—H = 0.90 Å (for NH₂), C—H = 0.96 Å (for CH₃) and C—H = 0.93 Å for aromatic H atoms, and they were constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(parent) for CH and NH, and U_iso(H) = 1.5U_eq(C) for CH₃.

S3. Results and discussion

Sulfameter polymorph III, (1) (Fig. 1a), and the sulfameter molecules in sulfameter dioxane solvate, (2) (Fig. 1b), and sulfameter tetra­hydro­furan solvate, (3) (Fig. 1c), crystallize in the imide tautomeric form with the H atoms bonded to N1A, the sulfono­midic N atom. This seems to be the preference for sulfameter structures (Giuseppetti et al., 1977; Caira, 1994).

The hydrogen bonding in all three structures is best described as three-dimensional and, unsurprisingly, the hydrogen-bonding patterns are quite distinct, with different hydrogen-bonding capabilities satisfied in all three structures (Tables 2, 3 and 4). Acceptors outnumber donors in all three structures and it is therefore not surprising that atoms O3A (in all three structures), N3A (in the polymorph only), O2B (in the dioxane solvate only) and O2A (in the THF solvate only) are unused. When longer and weaker hydrogen bonds are taken into consideration, all three structures acquire one extra contact, giving rise to bifurcated hydrogen bonds (Tables 2, 3 and 4).

The two conformations, sulfameter molecule A (red) and sulfameter molecule B (blue), of compound (1) are compared (superimposed) by structural overlay in Fig. 2(a), revealing a drastic difference in conformation, evidenced by the structural overlay value (root mean-square deviation, r.m.s.d.) of 0.7984 Å. The maximum difference of 1.4899 Å occurs between sulfameter molecule A and molecule B due to the sulfono­midic N atom. Bond lengths and angles in the SMT group are not significantly different across the three crystal structures, but the molecular conformations reflect the conformational freedom associated with the heterocyclic ring and meth­oxy group, as demonstrated in the structural overlay of Fig. 2(b) and in a comparison of selected torsion angles (Table 6). The maximum difference of 0.1878 Å occurring between the SMT groups of compounds (2) (purple) and (3) (green) is due to the phenyl atom C3A. Fig. 2(c) shows a superimposition of the sulfameter molecule of compounds (2) and (3) with molecule A of compound (1), and Fig. 2(d) shows the analogous comparison with molecule B of compound (1). These plots show that the sulfameter molecule A of compound (1) adopts nearly the same conformation as compounds (2) and (3), whereas the conformation of sulfameter molecule B is quite different from those of (2) and (3).

When comparing the same molecule in different crystal environments, Hirshfeld surfaces and fingerprint plots (McKinnon et al., 1998, 2004; Spackman & McKinnon, 2002) have been shown to be a powerful tool for elucidating and comparing inter­molecular inter­actions, complementing other tools currently available for the visualization of crystal structures and for their systematic description and analysis, e.g. graph-set analysis (Etter et al., 1990) and topological analysis (Blatov, 2006).

The number of Hirshfeld surfaces that are unique in a given crystal structure depends on the number of independent molecules in the asymmetric unit, implying that for compounds (2) and (3) there are two resulting surfaces for each structure, viz. one for the solute and one for the solvent. Hirshfeld surfaces for sulfameter polymorph (1) and sulfameter solvates (2) and (3) are shown in Figs. 3 and 4, respectively (for the sulfameter polymorph, sulfameter dioxane solvate and sulfameter tetra­hydro­furan solvate, a fully ordered SMT model was used); fingerprint plots for sulfameter polymorph (1), sulfameter dioxane solvate (2) and sulfameter tetra­hydro­furan solvate (3) are shown in Fig. 5; d_e and d_i are defined as the distance from the surface to the nearest atom external and inter­nal to the surface, respectively. The three-dimensional d_norm surfaces are mapped over a fixed colour scale of -0.5 (red) to 1.3 Å (blue), and the d_e surfaces are mapped in the range of 0.7–2.5 [Units? Å?]. The surfaces are shown as transparent to allow visualization of the SMT group, in a similar orientation for all three structures, around which they are calculated. It is clear that the information present in Tables 2, 3 and 4 is summarized effectively by these plots, with the large circular depressions (deep red) visible on the surfaces indicative of hydrogen-bonding contacts. The weak intra­molecular hydrogen bonds are not visible on the Hirshfeld surfaces. The Hirshfeld surfaces are coloured to highlight close contacts of the surface with the atoms of neighbouring species (molecule/ion) in the crystal structure, and the curvature of the surfaces is used to determine the overall coordination of each species in the crystal structure. For comparison of the inter­molecular inter­action schemes in the crystal structures, the normalized contact distances, d_norm, based on van der Waals radii, are mapped into the Hirshfeld surfaces. In the colour scale, negative values of d_norm are visualized by the red colour, indicating contacts shorter than the sum of the van der Waals radii. White denotes inter­molecular distances close to van der Waals contacts with d_norm equal to zero. In turn, contacts longer than the sum of the van der Waals radii with positive d_norm values are indicated by blue.

The feature labelled 1 on the Hirshfeld surface of compound (1) is indicative of a long N—H···O inter­action [H—A = 2.22 Å, D—A = 3.072 (2) Å and D—H···A = 170.6°], where the amino N atom is the donor and the meth­oxy O atom is the acceptor. Similarly, the feature labelled 2 also indicates a long N—H···O inter­action [H—A = 2.12 (2) Å, D—A = 2.917 (2) Å and D—H···A = 172 (2)°], where the sulfonamidic N atom is the donor and a sulfone O atom is the acceptor. Both inter­actions are shown as deep-red spots in Fig. 3(a) for the whole crystal and both sulfameter molecules A and B. The features labelled 3 and 4 in Fig. 3(a), of small extent and light in colour, indicate a C—H···O inter­action. The feature labelled 5 is indicative of a long N—H···N inter­action [H—A = 2.58 Å, D—A = 3.292 (2) Å and D—H···A = 140.7°], where the amino N atom is the donor and a pyrimidine N atom is the acceptor. Similarly, the feature labelled 6 also indicates a long N—H···N inter­action [H—A = 2.19 (2) Å, D—A = 2.982 (2) Å and D—H···A = 174 (2)°], where the sulfonamidic N atom is the donor and a pyrimidine N atom is the acceptor. These two N—H···N inter­actions are shown as dark-red spots in Fig. 3(b) for the whole crystal and both sulfameter molecules A and B. The features labelled 7 and 8 in Fig. 3(b) describe the C—H···N inter­action and H···H contacts, shown as back views for compound (1) for the whole crystal and both sulfameter molecules A and B. The different conformations adopted by the SMT group can be partly understood in terms of favourable inter­actions formed with the two sulfameter molecules A and B. The C—H···π inter­actions in both sulfameter molecules A and B for the whole crystal are visible in Figs. 3(a) and 3(b) as a large deep depression above and below the amino group, respectively, and are labelled 9. The geometry of this inter­action involves an H···Cg (Cg is the ring centroid) distance of 2.88 Å and a C—H···Cg bond angle of 140°. This inter­action is not observed in either of the sulfameter (dioxane and tetra­hydro­furan) solvates, (2) or (3).

The feature labelled 1 on the Hirshfeld surface of compound (2) is indicative of a long N—H···N inter­action [H—A = 2.47 Å, D—A = 3.171 (2) Å and D—H···A = 139.7°], where the amino N atom is the donor and a pyrimidine N atom is the acceptor. Similarly, that for compound (3) is indicative of a long N—H···N inter­action [H—A = 2.45 Å, D—A = 3.167 (2) Å and D—H···A = 140.7°], where the amino N atom is the donor and a pyrimidine N atom is the acceptor. These types of inter­action for compounds (2) and (3) are shown as dark-red spots in Figs. 4(b) and 4(e). The feature labelled 2 on the Hirshfeld surfaces of compounds (2) and (3), of small extent and light in colour, is indicative of a C—H···O inter­action, where a phenyl C atom is the donor and a sulfone O atom is the acceptor. This type of contact is weaker and longer than other hydrogen bonds. The feature labelled 3 for compounds (2) and (3) in Fig. 4 shows H···H contacts. The pattern of the flat region labelled 4 (blue–green) for both solvates (2) and (3) in Fig. 4 is characteristic of an offset π–π ring stacking.

A fingerprint plot is a two-dimensional representation of the Hirshfeld surface in which the distances of the nearest atoms outside, d_e, and inside, d_i, the Hirshfeld surface are plotted for evenly spaced points on the Hirshfeld surface and the points are coloured as a function of the fraction of surface points, ranging from blue (relatively few points) through green (moderate fraction) to red (highest fraction). The resulting distance pair points in the plane are coloured according to their densities and, like the Hirshfeld surfaces, these fingerprint plots are also unique for a symmetry-unique molecule/ion in a crystal structure (Jayatilaka et al., 2006). Thus, Hirshfeld surfaces and two-dimensional fingerprint plots are useful graphical tools for analysing inter­molecular inter­actions in different polymorphs of one molecule in different crystals, providing an easy and quick comparison of polymorphs (McKinnon, Fabbiani & Spackman, 2007; Durka et al., 2011). The d_norm (normalized contact distance) surface and the breakdown of fingerprint plots (McKinnon, Jayatilaka & Spackman, 2007) are used for visualizing and qu­anti­fying the inter­molecular inter­actions in crystal structures.

The two-dimensional fingerprint plots are deconvoluted to highlight particular atom pair close contacts. This deconvolution enables the separation of contributions from different inter­action types, which overlap in the full fingerprint. The two-dimensional fingerprint plots for compounds (1), (2) and (3), which analyse all inter­molecular contacts at the same time (Fig. 5), reveal that the main inter­molecular inter­actions in these compounds are H···H, H···O, H···C and H···N types (Figs. 6, 7 and 8). The H···H contacts for all three compounds, which are reflected in the middle of the scattered points and cover the greatest area in the two-dimensional fingerprint plots, have the most significant contribution to the total Hirshfeld surfaces. At the top left and bottom right of the fingerprint plots [In which figure?], there are characteristic wings which are identified as being a result of C—H contacts. The O—H contacts appear as distinct spikes pointing towards the lower left of the plots and H—O contacts appear as distinct spikes pointing towards the top left of the plots. These fingerprint plots are quite asymmetric, and this is because the inter­actions occur between two chemically and crystallographically distinct molecules. Complementary regions are visible in the fingerprint plots where one molecule acts as a donor (d_e > d_i) and the other as an acceptor (d_e < d_i). The shortest contact, i.e. the minimum value of (d_e + d_i), is around 1.9 Å, indicating the importance of these inter­actions. Fig. 9 contains the percentage contributions for a variety of contacts in all three crystal structures. Thus, the nature of the inter­play of the title sulfameter is more easily understood using Hirshfeld surfaces, with the results further highlighting the power of the technique in mapping out the inter­actions within the crystal structure, and this methodology has very important promise in crystal engineering. Undoubtedly the Hirshfeld surface allows much more detailed scrutiny by displaying all the inter­molecular inter­actions and by qu­anti­fying them in a two-dimensional fingerprint plot within the crystal structure. It is thus a novel tool in crystal structure prediction.

Each of the solvate structures (2) and (3) reported here crystallizes with one solvent molecule per asymmetric unit, while the structure of polymorph III of sulfameter, (1), crystallizes with two molecules per asymmetric unit. The conformation of the sulfameter molecules can be best described in terms of the angles between the three planar groups (i.e. the C1A/S1A/N1A plane, the benzene ring plane and the pyrimidine ring plane) and rotation around the C1A—S1A, S1A—N1A and N1A—C7A bonds. The angles between different planes are given in Table 5 and the torsion angles describing these rotations are given in Table 6. The solvate structures are generally similar to each other, although there is some rotational flexibility in the torsion angles, resulting in a range of approximately 3° in the orientation of the benzene rings (described by the torsion angle N1A—S1A—C1A—C2A), from -74.15 (14)° in the tetra­hydro­furan solvate, (3), to -77.0 (2)° in the dioxane solvate, (2). The orientation of the pyrimidine rings (described by the torsion angle S1A—N1A—C7A—N2A) shows a variation range of approximately 10°, from -25.3 (2)° in the tetra­hydro­furan solvate, (3), to -15.5 (4)° in the dioxane solvate, (2). This torsion angle in (1) [152.67 (15)° for molecule A and 17.3 (2)° for molecule B] suggests that the pyrimidine ring plane is flipped over relative to the pyrimidine rings in the solvate structures. Also, the orientation of the pyrimidine rings (described by the torsion angle S1A—N1A—C7A—N3A) shows a range of approximately 10°, from 156.66 (12)° in the tetra­hydro­furan solvate, (3), to 166.1 (2)° in the dioxane solvate, (2). These torsion angles in (1) are -29.3 (2)° for molecule A and -162.86 (13)° for molecule B. The planes of the benzene and pyrimidine rings are consistently perpendicular in all three structures, with dihedral angles ranging from 80.89 (10)° and 86.89 (9)° for molecules A and B, respectively in the polymorph III of sulfameter, (1), to 86.85 (14)° in the dioxane solvate, (2), and 86.57 (8)° in the tetra­hydro­furan solvate, (3). The reported dihedral angle between the phenyl and isoxazole rings in the silver complex of sulfamethoxazole is 85.6 (4)° (Tailor & Patel, 2015a or b?), while the angle between the phenyl and pyrimidine rings in the silver complex of sulfamethazine is 81.35 (13)° (Tailor & Patel, 2015a or b?). The solvent in each of the solvate structures is located between these planes, with the centre of mass of the solvate approximately bis­ecting this dihedral angle, resulting in an approximately equal distance between the centre of mass of the solvate and the centres of mass of the pyrimidine and benzene ring planes. The variations in the molecular structures of the sulfameter molecules suggest that they are conformational polymorphs.

An inter­molecular π–π inter­action is observed between the centroids of the two pyrimidine rings of (1), with a distance of 3.8660 (11) Å, while an intra­molecular π–π inter­action is observed between the centroids of the pyrimidine rings and phenyl rings in the crystal structures of (2) and (3) [Distances for these two compounds as well?]. Strong N—H···N and N—H···O inter­actions (Fig. 10), along with π–π and C—H···π ring inter­actions, contribute to the stability of the molecular packing of (1). The N atoms of aniline (N4A) and pyrimidine (N2A) form a significant N—H···N inter­action, as shown in Fig. 11. Very similar and inter­esting hydrogen-bond patterns are observed in both sulfameter solvates. In another inter­action, pyrimidine (N3A) and sulfonamide (N1A) N atoms of symmetry-related molecules are inter­connected to form a strong crystal packing in both (2) and (3) (Fig. 12). In both sulfameter solvates, the sulfonamide and pyrimidine N atoms form a dimer. In the crystal structure of (3), atom O1B of the tetra­hydro­furan solvent molecule acts as a donor, forming an inter­molecular C—H···O hydrogen bond with pyrimidine atom C9A, which contributes to the stability of the crystal packing (Fig. 13).

S3.1. Supplementary data

Full crystallographic data for the structures reported in this article have been deposited with the Cambridge Crystallographic Data Centre for (1), (2) and (3), CCDC Nos. 1006461, 1006661 and 1006508, respectively. Copies of this information can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (Fax [phone]; e-mail [e-mail]).

Related literature

For related literature, see: Blatov (2006); Bruker (2008); Byrn et al. (1999); Caira (1994); Caira & Mohamed (1993); Durka et al. (2011); Etter et al. (1990); Farrugia (2012); Giuseppetti et al. (1977); Jayatilaka et al. (2006); Lee et al. (2011); McKinnon et al. (1998, 2004); McKinnon, Fabbiani & Spackman (2007); McKinnon, Jayatilaka & Spackman (2007); Pratt et al. (2011); Sheldrick (2008); Spackman & McKinnon (2002); Spek (2009); Tailor & Patel (2015a,b); Westrip (2010); Wolff (1996).

Computing details

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP 3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. The molecular structures of (a) polymorph III of sulfameter, (1), (b) sulfameter dioxane solvate, (2), and (c) sulfameter tetrahydrofuran solvate, (3), all at 296 K, showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 50% probability level. [All the labels are rather faint and somewhat distorted. Can a revised plot be supplied?]
	Fig. 2. Structural overlays of the SMT groups. (a) Compound (1) [sulfameter molecules A (red) and B (blue)], with a root mean-square deviation (r.m.s.d.) of the overlay fit of 0.7984 Å. (b) Compounds (2) and (3) [sulfameter dioxane solvate (purple) and sulfameter tetrahydrofuran solvate (green)], with an r.m.s.d. of the overlay fit of 0.1060 Å. (c) Molecule A of (1) with compounds (2) and (3), with r.m.s.d.'s of the overlay fits between (1) and (2) of 0.1907 Å and between (1) and (3) of 0.1061 Å. (d) Molecule B of (1) with compounds (2) and (3), with r.m.s.d.'s of the overlay fits between (1) and (2) of 0.8656 Å and between (1) and (3) of 0.8258 Å.
	Fig. 3. (a) Front and (b) back views of the Hirshfeld surfaces for sulfameter polymorph III, (1) (Hirshfeld surface mapped with dnorm). The labels are referred to in the text.
	Fig. 4. Hirshfeld surfaces for (a) and (d) the whole crystal, (b) and (e) the sulfameter, and (c) and (f) the solvent of sulfameter dioxane solvate, (2), and sulfameter tetrahydrofuran solvate, (3). (Hirshfeld surface mapped with de). The labels are referred to in the text.
	Fig. 5. Fingerprint plots. For sulfameter polymorph III, (1): (a) the whole crystal, (b) sulfameter molecule A and (c) sulfameter molecule B. For sulfameter dioxane solvate, (2): (a) the whole crystal, (b) sulfameter and (c) dioxane. For sulfameter tetrahydrofuran solvate, (3): (a) the whole crystal, (b) sulfameter and (c) tetrahydrofuran. Close contacts are labelled as follows: H···H 1, O···H 2, C···H 3 and N···H 4.
	Fig. 6. Two-dimensional fingerprint plots of sulfameter polymorph III, (1), resolved into (a) H···H, (b) H···O, (c) H···C and (d) H···N contacts for the whole crystal, sulfameter molecule A and sulfameter molecule B, showing the percentage of contacts contributed to the total Hirshfeld surface area of the molecule.
	Fig. 7. Two-dimensional fingerprint plots of sulfameter dioxane solvate, (2), resolved into (a) H···H, (b) H···O, (c) H···C and (d) H···N contacts for the whole crystal, dioxane solvent and sulfameter molecule, showing the percentage of contacts contributed to the total Hirshfeld surface area of the molecule.
	Fig. 8. Two-dimensional fingerprint plots of sulfameter tetrahydrofuran solvate, (3), resolved into (a) H···H, (b) H···O, (c) H···C and (d) H···N contacts for the whole crystal, tetrahydrofuran solvent and sulfameter molecule, showing the percentage of contacts contributed to the total Hirshfeld surface area of the molecule.
	Fig. 9. The relative contributions of various interactions to the Hirshfeld surface area of compounds (1), (2) and (3).
	Fig. 10. A packing diagram showing the hydrogen-bonding interactions in compound (1). (Symmetry codes as in Table 2.) [Please provide a revised version showing the axes labels and origin]
	Fig. 11. A packing diagram showing the hydrogen-bonding interactions in compound (2). (Symmetry codes as in Table 3.)
	Fig. 12. A packing diagram showing the hydrogen-bonding interactions in compound (3). (Symmetry codes as in Table 4.)
	Fig. 13. A packing diagram showing the intermolecular C—H···O hydrogen-bonding interactions in compound (3). (Symmetry codes as in Table 4.)

(1) 4-Amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide

Crystal data

C11H12N4O3S	F(000) = 1168
Mr = 280.31	Dx = 1.492 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8253 reflections
a = 8.3560 (3) Å	θ = 2.4–26.8°
b = 26.8244 (10) Å	µ = 0.27 mm^−1
c = 11.8293 (4) Å	T = 296 K
β = 109.730 (1)°	Needle, colourless
V = 2495.82 (15) Å^3	0.44 × 0.14 × 0.11 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer	4408 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
Graphite monochromator	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −9→10
22168 measured reflections	k = −34→34
5741 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 0.7408P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5741 reflections	Δρmax = 0.25 e Å^−3
351 parameters	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.

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

	x	y	z	Uiso*/Ueq
S1A	0.57849 (6)	0.06562 (2)	0.28039 (4)	0.04237 (13)
S1B	1.56103 (6)	0.22290 (2)	1.02391 (4)	0.04458 (14)
O1A	0.63703 (17)	0.10872 (5)	0.23303 (12)	0.0538 (4)
O1B	1.5747 (2)	0.24355 (5)	0.91703 (13)	0.0614 (4)
O2A	0.69895 (16)	0.03786 (5)	0.37313 (12)	0.0544 (4)
O2B	1.70381 (18)	0.22474 (6)	1.13295 (14)	0.0621 (4)
O3A	0.16250 (19)	−0.14323 (5)	0.14340 (12)	0.0572 (4)
O3B	0.99352 (17)	0.07521 (5)	0.66748 (12)	0.0525 (3)
N1A	0.4961 (2)	0.03061 (6)	0.16132 (15)	0.0433 (4)
N1B	1.5257 (2)	0.16241 (6)	1.00524 (15)	0.0430 (4)
N2A	0.2910 (2)	−0.02395 (6)	0.05143 (14)	0.0496 (4)
N2B	1.2940 (2)	0.16795 (6)	0.82774 (13)	0.0458 (4)
N3A	0.4376 (2)	−0.03955 (6)	0.25758 (14)	0.0470 (4)
N3B	1.35942 (18)	0.09280 (5)	0.94062 (13)	0.0390 (3)
N4A	0.0066 (2)	0.12458 (7)	0.43647 (16)	0.0628 (5)
H4A1	0.0008	0.1142	0.5038	0.075*
H4A2	−0.0717	0.1436	0.3911	0.075*
N4B	0.9688 (2)	0.30532 (7)	1.12390 (19)	0.0650 (5)
H4B1	0.8932	0.3226	1.0709	0.078*
H4B2	0.9589	0.3000	1.1929	0.078*
C1A	0.4125 (2)	0.08333 (7)	0.32901 (15)	0.0392 (4)
C1B	1.3840 (2)	0.24826 (7)	1.04925 (16)	0.0385 (4)
C2A	0.4025 (2)	0.06627 (7)	0.43725 (16)	0.0426 (4)
H2A	0.4869	0.0454	0.4857	0.051*
C2B	1.3677 (3)	0.24059 (7)	1.16124 (17)	0.0476 (5)
H2B	1.4506	0.2228	1.2200	0.057*
C3A	0.2693 (3)	0.07991 (7)	0.47310 (16)	0.0449 (4)
H3A	0.2647	0.0685	0.5462	0.054*
C3B	1.2294 (3)	0.25916 (8)	1.18507 (18)	0.0521 (5)
H3B	1.2187	0.2536	1.2598	0.063*
C4A	0.1400 (2)	0.11077 (7)	0.40163 (16)	0.0448 (4)
C4B	1.1049 (3)	0.28621 (7)	1.09833 (18)	0.0455 (5)
C5A	0.1537 (3)	0.12903 (9)	0.29455 (19)	0.0579 (5)
H5A	0.0716	0.1508	0.2474	0.070*
C5B	1.1241 (3)	0.29421 (7)	0.98759 (18)	0.0505 (5)
H5B	1.0432	0.3128	0.9294	0.061*
C6A	0.2868 (3)	0.11520 (8)	0.25824 (18)	0.0542 (5)
H6A	0.2931	0.1271	0.1861	0.065*
C6B	1.2617 (3)	0.27489 (7)	0.96275 (17)	0.0468 (5)
H6B	1.2719	0.2799	0.8876	0.056*
C7A	0.4025 (2)	−0.01308 (6)	0.15746 (15)	0.0382 (4)
C7B	1.3855 (2)	0.14026 (6)	0.91969 (15)	0.0357 (4)
C8A	0.0450 (3)	−0.16135 (9)	0.0348 (2)	0.0612 (6)
H8A3	0.0018	−0.1930	0.0489	0.092*
H8A2	0.1008	−0.1651	−0.0236	0.092*
H8A1	−0.0473	−0.1382	0.0054	0.092*
C8B	0.9616 (3)	0.02293 (8)	0.6725 (2)	0.0598 (6)
H8B1	0.8647	0.0137	0.6047	0.090*
H8B3	0.9396	0.0156	0.7453	0.090*
H8B2	1.0592	0.0045	0.6709	0.090*
C9A	0.2089 (3)	−0.06759 (7)	0.04385 (18)	0.0513 (5)
H9A	0.1303	−0.0771	−0.0296	0.062*
C9B	1.1645 (3)	0.14472 (7)	0.74758 (17)	0.0468 (4)
H9B	1.0953	0.1628	0.6822	0.056*
C10A	0.2371 (2)	−0.09854 (7)	0.14069 (17)	0.0430 (4)
C10B	1.1277 (2)	0.09482 (7)	0.75701 (15)	0.0388 (4)
C11A	0.3532 (3)	−0.08202 (7)	0.24761 (18)	0.0495 (5)
H11A	0.3731	−0.1017	0.3158	0.059*
C11B	1.2300 (2)	0.06991 (6)	0.85685 (16)	0.0404 (4)
H11B	1.2091	0.0364	0.8666	0.049*
H1A	0.464 (3)	0.0458 (8)	0.1006 (19)	0.049 (6)*
H1B	1.566 (3)	0.1474 (8)	1.067 (2)	0.055 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0388 (2)	0.0458 (3)	0.0358 (2)	−0.00306 (19)	0.00378 (18)	0.00431 (19)
S1B	0.0485 (3)	0.0447 (3)	0.0471 (3)	−0.0149 (2)	0.0248 (2)	−0.0106 (2)
O1A	0.0507 (8)	0.0568 (9)	0.0468 (8)	−0.0162 (6)	0.0071 (6)	0.0058 (7)
O1B	0.0831 (10)	0.0546 (9)	0.0674 (10)	−0.0170 (8)	0.0527 (9)	−0.0045 (7)
O2A	0.0420 (7)	0.0640 (9)	0.0468 (8)	0.0060 (6)	0.0012 (6)	0.0111 (7)
O2B	0.0454 (8)	0.0724 (10)	0.0652 (10)	−0.0215 (7)	0.0143 (7)	−0.0222 (8)
O3A	0.0679 (9)	0.0459 (8)	0.0506 (8)	−0.0111 (7)	0.0107 (7)	0.0017 (7)
O3B	0.0544 (8)	0.0478 (8)	0.0439 (7)	−0.0084 (6)	0.0015 (6)	−0.0028 (6)
N1A	0.0519 (9)	0.0419 (9)	0.0338 (8)	−0.0030 (7)	0.0115 (7)	0.0045 (7)
N1B	0.0460 (9)	0.0414 (9)	0.0390 (9)	−0.0056 (7)	0.0108 (7)	−0.0034 (7)
N2A	0.0601 (10)	0.0465 (9)	0.0358 (8)	−0.0049 (8)	0.0080 (8)	0.0045 (7)
N2B	0.0595 (10)	0.0363 (8)	0.0371 (8)	−0.0048 (7)	0.0104 (7)	0.0023 (7)
N3A	0.0572 (10)	0.0421 (9)	0.0363 (8)	−0.0018 (7)	0.0086 (7)	0.0054 (7)
N3B	0.0427 (8)	0.0336 (8)	0.0385 (8)	−0.0007 (6)	0.0110 (7)	0.0002 (6)
N4A	0.0605 (11)	0.0749 (13)	0.0542 (11)	0.0116 (9)	0.0211 (9)	0.0054 (10)
N4B	0.0673 (12)	0.0543 (11)	0.0854 (14)	0.0022 (9)	0.0416 (11)	−0.0069 (10)
C1A	0.0438 (9)	0.0366 (9)	0.0303 (8)	−0.0021 (8)	0.0036 (7)	0.0006 (7)
C1B	0.0493 (10)	0.0347 (9)	0.0358 (9)	−0.0103 (8)	0.0200 (8)	−0.0070 (7)
C2A	0.0504 (10)	0.0360 (10)	0.0329 (9)	0.0024 (8)	0.0030 (8)	0.0039 (7)
C2B	0.0590 (12)	0.0512 (12)	0.0354 (10)	0.0023 (9)	0.0195 (9)	0.0023 (8)
C3A	0.0607 (12)	0.0391 (10)	0.0316 (9)	−0.0040 (9)	0.0113 (9)	0.0017 (8)
C3B	0.0750 (14)	0.0509 (12)	0.0420 (11)	−0.0030 (10)	0.0349 (11)	−0.0006 (9)
C4A	0.0491 (10)	0.0422 (10)	0.0389 (10)	−0.0035 (8)	0.0094 (8)	−0.0046 (8)
C4B	0.0539 (11)	0.0333 (9)	0.0548 (12)	−0.0098 (8)	0.0255 (10)	−0.0107 (9)
C5A	0.0566 (12)	0.0676 (14)	0.0444 (11)	0.0185 (11)	0.0102 (10)	0.0180 (10)
C5B	0.0593 (12)	0.0430 (11)	0.0475 (11)	−0.0003 (9)	0.0159 (10)	0.0018 (9)
C6A	0.0573 (12)	0.0649 (14)	0.0362 (10)	0.0106 (10)	0.0102 (9)	0.0181 (9)
C6B	0.0653 (12)	0.0433 (11)	0.0353 (10)	−0.0090 (9)	0.0213 (9)	−0.0005 (8)
C7A	0.0427 (9)	0.0370 (9)	0.0353 (9)	0.0054 (7)	0.0138 (8)	−0.0004 (7)
C7B	0.0398 (9)	0.0361 (9)	0.0332 (9)	−0.0015 (7)	0.0151 (7)	−0.0038 (7)
C8A	0.0604 (13)	0.0595 (14)	0.0608 (14)	−0.0134 (11)	0.0165 (11)	−0.0109 (11)
C8B	0.0579 (12)	0.0437 (12)	0.0694 (14)	−0.0092 (10)	0.0105 (11)	−0.0132 (11)
C9A	0.0579 (12)	0.0498 (12)	0.0387 (10)	−0.0046 (9)	0.0065 (9)	−0.0011 (9)
C9B	0.0579 (11)	0.0415 (10)	0.0350 (10)	−0.0003 (9)	0.0077 (9)	0.0048 (8)
C10A	0.0495 (10)	0.0366 (10)	0.0441 (10)	0.0033 (8)	0.0174 (9)	0.0001 (8)
C10B	0.0417 (9)	0.0397 (10)	0.0336 (9)	−0.0017 (8)	0.0109 (8)	−0.0026 (8)
C11A	0.0609 (12)	0.0421 (11)	0.0402 (10)	0.0003 (9)	0.0101 (9)	0.0082 (9)
C11B	0.0458 (10)	0.0314 (9)	0.0423 (10)	−0.0024 (8)	0.0125 (8)	−0.0011 (8)

Geometric parameters (Å, º)

S1A—O2A	1.4232 (14)	C1B—C6B	1.377 (3)
S1A—O1A	1.4406 (14)	C1B—C2B	1.392 (2)
S1A—N1A	1.6385 (17)	C2A—C3A	1.368 (3)
S1A—C1A	1.7371 (19)	C2A—H2A	0.9300
S1B—O1B	1.4198 (14)	C2B—C3B	1.372 (3)
S1B—O2B	1.4320 (15)	C2B—H2B	0.9300
S1B—N1B	1.6507 (17)	C3A—C4A	1.396 (3)
S1B—C1B	1.7435 (18)	C3A—H3A	0.9300
O3A—C10A	1.356 (2)	C3B—C4B	1.393 (3)
O3A—C8A	1.414 (2)	C3B—H3B	0.9300
O3B—C10B	1.362 (2)	C4A—C5A	1.398 (3)
O3B—C8B	1.432 (2)	C4B—C5B	1.389 (3)
N1A—C7A	1.401 (2)	C5A—C6A	1.372 (3)
N1A—H1A	0.79 (2)	C5A—H5A	0.9300
N1B—C7B	1.396 (2)	C5B—C6B	1.381 (3)
N1B—H1B	0.80 (2)	C5B—H5B	0.9300
N2A—C7A	1.318 (2)	C6A—H6A	0.9300
N2A—C9A	1.345 (2)	C6B—H6B	0.9300
N2B—C7B	1.326 (2)	C8A—H8A3	0.9600
N2B—C9B	1.329 (2)	C8A—H8A2	0.9600
N3A—C11A	1.324 (2)	C8A—H8A1	0.9600
N3A—C7A	1.326 (2)	C8B—H8B1	0.9600
N3B—C7B	1.329 (2)	C8B—H8B3	0.9600
N3B—C11B	1.343 (2)	C8B—H8B2	0.9600
N4A—C4A	1.364 (3)	C9A—C10A	1.369 (3)
N4A—H4A1	0.8600	C9A—H9A	0.9300
N4A—H4A2	0.8600	C9B—C10B	1.386 (3)
N4B—C4B	1.371 (2)	C9B—H9B	0.9300
N4B—H4B1	0.8600	C10A—C11A	1.382 (3)
N4B—H4B2	0.8600	C10B—C11B	1.375 (2)
C1A—C2A	1.389 (2)	C11A—H11A	0.9300
C1A—C6A	1.394 (3)	C11B—H11B	0.9300
O2A—S1A—O1A	118.37 (8)	N4B—C4B—C5B	121.3 (2)
O2A—S1A—N1A	110.21 (9)	N4B—C4B—C3B	120.08 (18)
O1A—S1A—N1A	103.00 (8)	C5B—C4B—C3B	118.65 (18)
O2A—S1A—C1A	108.89 (8)	C6A—C5A—C4A	120.79 (19)
O1A—S1A—C1A	108.84 (9)	C6A—C5A—H5A	119.6
N1A—S1A—C1A	106.89 (8)	C4A—C5A—H5A	119.6
O1B—S1B—O2B	119.72 (9)	C6B—C5B—C4B	120.83 (19)
O1B—S1B—N1B	109.20 (9)	C6B—C5B—H5B	119.6
O2B—S1B—N1B	102.20 (9)	C4B—C5B—H5B	119.6
O1B—S1B—C1B	109.19 (9)	C5A—C6A—C1A	120.29 (18)
O2B—S1B—C1B	109.20 (9)	C5A—C6A—H6A	119.9
N1B—S1B—C1B	106.42 (8)	C1A—C6A—H6A	119.9
C10A—O3A—C8A	117.77 (16)	C1B—C6B—C5B	119.94 (17)
C10B—O3B—C8B	117.51 (15)	C1B—C6B—H6B	120.0
C7A—N1A—S1A	125.12 (13)	C5B—C6B—H6B	120.0
C7A—N1A—H1A	112.8 (16)	N2A—C7A—N3A	127.15 (17)
S1A—N1A—H1A	113.7 (16)	N2A—C7A—N1A	115.05 (16)
C7B—N1B—S1B	125.72 (14)	N3A—C7A—N1A	117.76 (16)
C7B—N1B—H1B	115.9 (16)	N2B—C7B—N3B	127.16 (16)
S1B—N1B—H1B	111.7 (16)	N2B—C7B—N1B	117.82 (16)
C7A—N2A—C9A	115.90 (16)	N3B—C7B—N1B	115.02 (16)
C7B—N2B—C9B	115.34 (16)	O3A—C8A—H8A3	109.5
C11A—N3A—C7A	115.50 (16)	O3A—C8A—H8A2	109.5
C7B—N3B—C11B	116.24 (15)	H8A3—C8A—H8A2	109.5
C4A—N4A—H4A1	120.0	O3A—C8A—H8A1	109.5
C4A—N4A—H4A2	120.0	H8A3—C8A—H8A1	109.5
H4A1—N4A—H4A2	120.0	H8A2—C8A—H8A1	109.5
C4B—N4B—H4B1	120.0	O3B—C8B—H8B1	109.5
C4B—N4B—H4B2	120.0	O3B—C8B—H8B3	109.5
H4B1—N4B—H4B2	120.0	H8B1—C8B—H8B3	109.5
C2A—C1A—C6A	119.21 (17)	O3B—C8B—H8B2	109.5
C2A—C1A—S1A	121.24 (14)	H8B1—C8B—H8B2	109.5
C6A—C1A—S1A	119.55 (14)	H8B3—C8B—H8B2	109.5
C6B—C1B—C2B	119.83 (17)	N2A—C9A—C10A	122.16 (18)
C6B—C1B—S1B	122.30 (13)	N2A—C9A—H9A	118.9
C2B—C1B—S1B	117.86 (15)	C10A—C9A—H9A	118.9
C3A—C2A—C1A	120.43 (17)	N2B—C9B—C10B	122.98 (17)
C3A—C2A—H2A	119.8	N2B—C9B—H9B	118.5
C1A—C2A—H2A	119.8	C10B—C9B—H9B	118.5
C3B—C2B—C1B	120.11 (19)	O3A—C10A—C9A	127.23 (18)
C3B—C2B—H2B	119.9	O3A—C10A—C11A	116.63 (17)
C1B—C2B—H2B	119.9	C9A—C10A—C11A	116.14 (18)
C2A—C3A—C4A	120.98 (17)	O3B—C10B—C11B	126.17 (16)
C2A—C3A—H3A	119.5	O3B—C10B—C9B	117.20 (16)
C4A—C3A—H3A	119.5	C11B—C10B—C9B	116.62 (17)
C2B—C3B—C4B	120.61 (17)	N3A—C11A—C10A	123.09 (17)
C2B—C3B—H3B	119.7	N3A—C11A—H11A	118.5
C4B—C3B—H3B	119.7	C10A—C11A—H11A	118.5
N4A—C4A—C3A	121.46 (17)	N3B—C11B—C10B	121.58 (16)
N4A—C4A—C5A	120.25 (18)	N3B—C11B—H11B	119.2
C3A—C4A—C5A	118.24 (18)	C10B—C11B—H11B	119.2
O2A—S1A—N1A—C7A	61.24 (17)	C2A—C1A—C6A—C5A	−0.8 (3)
O1A—S1A—N1A—C7A	−171.57 (15)	S1A—C1A—C6A—C5A	179.15 (17)
C1A—S1A—N1A—C7A	−56.95 (17)	C2B—C1B—C6B—C5B	0.5 (3)
O1B—S1B—N1B—C7B	−61.03 (17)	S1B—C1B—C6B—C5B	−179.94 (15)
O2B—S1B—N1B—C7B	171.21 (15)	C4B—C5B—C6B—C1B	−1.4 (3)
C1B—S1B—N1B—C7B	56.71 (17)	C9A—N2A—C7A—N3A	−2.5 (3)
O2A—S1A—C1A—C2A	−6.43 (18)	C9A—N2A—C7A—N1A	175.30 (16)
O1A—S1A—C1A—C2A	−136.78 (15)	C11A—N3A—C7A—N2A	1.7 (3)
N1A—S1A—C1A—C2A	112.61 (16)	C11A—N3A—C7A—N1A	−176.01 (17)
O2A—S1A—C1A—C6A	173.64 (16)	S1A—N1A—C7A—N2A	152.67 (15)
O1A—S1A—C1A—C6A	43.29 (18)	S1A—N1A—C7A—N3A	−29.3 (2)
N1A—S1A—C1A—C6A	−67.32 (18)	C9B—N2B—C7B—N3B	−1.3 (3)
O1B—S1B—C1B—C6B	13.09 (18)	C9B—N2B—C7B—N1B	178.50 (16)
O2B—S1B—C1B—C6B	145.71 (15)	C11B—N3B—C7B—N2B	2.8 (3)
N1B—S1B—C1B—C6B	−104.66 (16)	C11B—N3B—C7B—N1B	−177.04 (14)
O1B—S1B—C1B—C2B	−167.33 (14)	S1B—N1B—C7B—N2B	17.3 (2)
O2B—S1B—C1B—C2B	−34.71 (17)	S1B—N1B—C7B—N3B	−162.86 (13)
N1B—S1B—C1B—C2B	74.93 (16)	C7A—N2A—C9A—C10A	1.0 (3)
C6A—C1A—C2A—C3A	1.1 (3)	C7B—N2B—C9B—C10B	−1.1 (3)
S1A—C1A—C2A—C3A	−178.84 (14)	C8A—O3A—C10A—C9A	1.7 (3)
C6B—C1B—C2B—C3B	0.5 (3)	C8A—O3A—C10A—C11A	−179.07 (18)
S1B—C1B—C2B—C3B	−179.06 (16)	N2A—C9A—C10A—O3A	−179.74 (18)
C1A—C2A—C3A—C4A	0.6 (3)	N2A—C9A—C10A—C11A	1.0 (3)
C1B—C2B—C3B—C4B	−0.6 (3)	C8B—O3B—C10B—C11B	−4.6 (3)
C2A—C3A—C4A—N4A	179.97 (18)	C8B—O3B—C10B—C9B	176.02 (17)
C2A—C3A—C4A—C5A	−2.5 (3)	N2B—C9B—C10B—O3B	−178.64 (17)
C2B—C3B—C4B—N4B	−178.87 (19)	N2B—C9B—C10B—C11B	1.9 (3)
C2B—C3B—C4B—C5B	−0.4 (3)	C7A—N3A—C11A—C10A	0.6 (3)
N4A—C4A—C5A—C6A	−179.6 (2)	O3A—C10A—C11A—N3A	178.83 (18)
C3A—C4A—C5A—C6A	2.8 (3)	C9A—C10A—C11A—N3A	−1.8 (3)
N4B—C4B—C5B—C6B	179.88 (18)	C7B—N3B—C11B—C10B	−1.8 (2)
C3B—C4B—C5B—C6B	1.4 (3)	O3B—C10B—C11B—N3B	−179.73 (16)
C4A—C5A—C6A—C1A	−1.2 (3)	C9B—C10B—C11B—N3B	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A1···O3B^i	0.86	2.22	3.072 (2)	171
N4B—H4B2···N2B^ii	0.86	2.58	3.292 (2)	141
C3B—H3B···O1B^ii	0.93	2.53	3.406 (2)	156
C8B—H8B2···O2A^iii	0.96	2.52	3.468 (3)	169
C11B—H11B···N2A^iv	0.93	2.62	3.332 (2)	134
N1A—H1A···N3B^v	0.79 (2)	2.19 (2)	2.982 (2)	174 (2)
N1B—H1B···O1A^iv	0.80 (2)	2.12 (2)	2.917 (2)	172 (2)

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

(2) 4-Amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide 1,4-dioxane monosolvate

Crystal data

C11H12N4O3S·C4H8O2	F(000) = 776
Mr = 368.41	Dx = 1.396 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8916 reflections
a = 8.0609 (3) Å	θ = 2.6–27.5°
b = 19.5195 (7) Å	µ = 0.22 mm^−1
c = 11.2668 (4) Å	T = 296 K
β = 98.672 (1)°	Parallelepiped, colourless
V = 1752.50 (11) Å^3	0.50 × 0.40 × 0.20 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	3343 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.022
Graphite monochromator	θmax = 27.6°, θmin = 2.1°
φ and ω scans	h = −10→10
15401 measured reflections	k = −25→25
4038 independent reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.074	w = 1/[σ^2(Fo^2) + (0.1526P)^2 + 1.4824P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.241	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 1.18 e Å^−3
4038 reflections	Δρmin = −0.86 e Å^−3
210 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.008 (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.

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

	x	y	z	Uiso*/Ueq
S1A	0.48206 (8)	0.32665 (3)	0.93660 (6)	0.0407 (3)
O1A	0.4634 (3)	0.31298 (11)	1.05888 (19)	0.0540 (5)
O1B	1.0044 (6)	0.5753 (3)	0.8043 (6)	0.1355 (17)
O2A	0.6017 (3)	0.28761 (10)	0.8831 (2)	0.0535 (5)
O2B	1.2148 (7)	0.5648 (5)	0.6388 (7)	0.212 (4)
O3A	0.6604 (3)	0.56637 (11)	0.56969 (19)	0.0574 (6)
N1A	0.5354 (3)	0.40773 (12)	0.9396 (2)	0.0442 (5)
N2A	0.5886 (3)	0.41719 (11)	0.7413 (2)	0.0449 (5)
N3A	0.5705 (3)	0.51487 (12)	0.8645 (2)	0.0439 (5)
N4A	−0.1893 (4)	0.30078 (18)	0.6475 (3)	0.0696 (8)
H4A1	−0.2762	0.3127	0.6785	0.084*
H4A2	−0.2009	0.2850	0.5755	0.084*
C1A	0.2860 (3)	0.31938 (13)	0.8477 (2)	0.0402 (6)
C1B	1.0833 (10)	0.5157 (3)	0.8032 (9)	0.138
H1B1	1.0142	0.4793	0.8277	0.165*
H1B2	1.1879	0.5170	0.8584	0.165*
C2A	0.1439 (4)	0.33895 (16)	0.8967 (3)	0.0494 (7)
H2A	0.1556	0.3562	0.9745	0.059*
C2B	1.1141 (11)	0.5045 (3)	0.6894 (10)	0.147 (3)
H2B1	1.0080	0.4984	0.6370	0.177*
H2B2	1.1775	0.4623	0.6880	0.177*
C3A	−0.0130 (4)	0.33271 (17)	0.8304 (3)	0.0547 (7)
H3A	−0.1070	0.3457	0.8637	0.066*
C3B	1.1457 (13)	0.6317 (7)	0.6790 (11)	0.179 (3)
H3B1	1.2276	0.6679	0.6767	0.215*
H3B2	1.0448	0.6440	0.6249	0.215*
C4A	−0.0330 (4)	0.30692 (16)	0.7128 (3)	0.0510 (7)
C4B	1.1092 (10)	0.6249 (3)	0.7942 (9)	0.130 (3)
H4B1	1.2124	0.6165	0.8486	0.156*
H4B2	1.0619	0.6675	0.8180	0.156*
C5A	0.1119 (4)	0.28806 (16)	0.6650 (3)	0.0525 (7)
H5A	0.1015	0.2714	0.5870	0.063*
C6A	0.2696 (4)	0.29396 (15)	0.7324 (3)	0.0470 (6)
H6A	0.3642	0.2808	0.6999	0.056*
C7A	0.5650 (3)	0.44768 (13)	0.8425 (2)	0.0375 (5)
C8A	0.6462 (6)	0.63875 (17)	0.5784 (4)	0.0702 (10)
H8A1	0.6729	0.6597	0.5065	0.105*
H8A2	0.7227	0.6549	0.6462	0.105*
H8A3	0.5335	0.6505	0.5884	0.105*
C9A	0.6213 (4)	0.45873 (15)	0.6534 (2)	0.0472 (6)
H9A	0.6403	0.4393	0.5812	0.057*
C10A	0.6280 (4)	0.52924 (14)	0.6649 (2)	0.0432 (6)
C11A	0.6025 (4)	0.55558 (14)	0.7746 (3)	0.0462 (6)
H11A	0.6077	0.6027	0.7865	0.055*
H1A	0.523 (7)	0.433 (3)	0.994 (5)	0.105 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0460 (4)	0.0304 (4)	0.0476 (4)	−0.0016 (2)	0.0133 (3)	0.0041 (2)
O1A	0.0710 (14)	0.0441 (11)	0.0480 (11)	−0.0050 (10)	0.0129 (9)	0.0101 (9)
O1B	0.093 (3)	0.117 (4)	0.199 (5)	−0.006 (3)	0.031 (3)	0.004 (3)
O2A	0.0491 (11)	0.0400 (10)	0.0739 (14)	0.0057 (8)	0.0175 (10)	0.0005 (9)
O2B	0.094	0.358 (11)	0.189	0.000	0.032	0.005
O3A	0.0858 (16)	0.0463 (12)	0.0443 (11)	−0.0002 (10)	0.0237 (10)	0.0068 (9)
N1A	0.0602 (14)	0.0327 (11)	0.0421 (12)	−0.0077 (10)	0.0159 (10)	0.0008 (9)
N2A	0.0571 (14)	0.0345 (11)	0.0447 (12)	−0.0039 (9)	0.0128 (10)	−0.0020 (9)
N3A	0.0569 (13)	0.0344 (11)	0.0428 (11)	−0.0053 (9)	0.0157 (9)	−0.0002 (9)
N4A	0.0557 (17)	0.074 (2)	0.077 (2)	0.0021 (15)	0.0032 (14)	−0.0111 (16)
C1A	0.0441 (13)	0.0318 (12)	0.0475 (14)	−0.0025 (9)	0.0162 (11)	0.0013 (10)
C1B	0.128	0.079	0.206	−0.015	0.028	−0.032
C2A	0.0527 (16)	0.0480 (15)	0.0515 (15)	−0.0004 (12)	0.0210 (12)	−0.0074 (12)
C2B	0.128	0.079	0.234 (8)	−0.015	0.028	−0.032
C3A	0.0465 (15)	0.0549 (17)	0.0669 (19)	0.0016 (12)	0.0221 (14)	−0.0049 (14)
C3B	0.129	0.206 (10)	0.198	−0.014	0.014	−0.025
C4A	0.0480 (15)	0.0444 (15)	0.0612 (17)	−0.0035 (12)	0.0103 (12)	0.0016 (13)
C4B	0.130 (5)	0.082 (4)	0.176 (7)	−0.008 (4)	0.016 (5)	−0.035 (4)
C5A	0.0600 (18)	0.0498 (16)	0.0493 (15)	−0.0029 (13)	0.0135 (13)	−0.0071 (12)
C6A	0.0513 (15)	0.0423 (14)	0.0516 (15)	−0.0012 (11)	0.0218 (12)	−0.0035 (11)
C7A	0.0371 (12)	0.0339 (12)	0.0421 (12)	−0.0034 (9)	0.0082 (9)	0.0015 (9)
C8A	0.108 (3)	0.0431 (17)	0.065 (2)	0.0001 (17)	0.030 (2)	0.0150 (15)
C9A	0.0623 (17)	0.0404 (14)	0.0405 (13)	−0.0016 (12)	0.0131 (12)	−0.0028 (11)
C10A	0.0500 (14)	0.0389 (13)	0.0419 (13)	−0.0003 (11)	0.0115 (11)	0.0040 (10)
C11A	0.0600 (16)	0.0352 (12)	0.0462 (14)	−0.0037 (11)	0.0176 (12)	0.0012 (10)

Geometric parameters (Å, º)

S1A—O2A	1.432 (2)	C1B—H1B2	0.9700
S1A—O1A	1.433 (2)	C2A—C3A	1.374 (5)
S1A—N1A	1.639 (2)	C2A—H2A	0.9300
S1A—C1A	1.745 (3)	C2B—H2B1	0.9700
O1B—C4B	1.300 (8)	C2B—H2B2	0.9700
O1B—C1B	1.326 (8)	C3A—C4A	1.404 (5)
O2B—C3B	1.516 (13)	C3A—H3A	0.9300
O2B—C2B	1.584 (11)	C3B—C4B	1.380 (11)
O3A—C10A	1.352 (3)	C3B—H3B1	0.9700
O3A—C8A	1.422 (4)	C3B—H3B2	0.9700
N1A—C7A	1.393 (3)	C4A—C5A	1.407 (4)
N1A—H1A	0.81 (6)	C4B—H4B1	0.9700
N2A—C7A	1.325 (3)	C4B—H4B2	0.9700
N2A—C9A	1.337 (4)	C5A—C6A	1.383 (4)
N3A—C7A	1.334 (3)	C5A—H5A	0.9300
N3A—C11A	1.342 (3)	C6A—H6A	0.9300
N4A—C4A	1.365 (4)	C8A—H8A1	0.9600
N4A—H4A1	0.8600	C8A—H8A2	0.9600
N4A—H4A2	0.8600	C8A—H8A3	0.9600
C1A—C6A	1.378 (4)	C9A—C10A	1.383 (4)
C1A—C2A	1.398 (4)	C9A—H9A	0.9300
C1B—C2B	1.360 (11)	C10A—C11A	1.383 (4)
C1B—H1B1	0.9700	C11A—H11A	0.9300
O2A—S1A—O1A	118.74 (14)	C4B—C3B—H3B1	109.7
O2A—S1A—N1A	109.35 (13)	O2B—C3B—H3B1	109.7
O1A—S1A—N1A	103.00 (13)	C4B—C3B—H3B2	109.7
O2A—S1A—C1A	108.90 (13)	O2B—C3B—H3B2	109.7
O1A—S1A—C1A	108.64 (14)	H3B1—C3B—H3B2	108.2
N1A—S1A—C1A	107.63 (13)	N4A—C4A—C3A	120.3 (3)
C4B—O1B—C1B	109.4 (6)	N4A—C4A—C5A	121.6 (3)
C3B—O2B—C2B	107.6 (6)	C3A—C4A—C5A	118.1 (3)
C10A—O3A—C8A	116.8 (2)	O1B—C4B—C3B	112.8 (8)
C7A—N1A—S1A	126.8 (2)	O1B—C4B—H4B1	109.0
C7A—N1A—H1A	108 (4)	C3B—C4B—H4B1	109.0
S1A—N1A—H1A	123 (4)	O1B—C4B—H4B2	109.0
C7A—N2A—C9A	115.8 (2)	C3B—C4B—H4B2	109.0
C7A—N3A—C11A	116.6 (2)	H4B1—C4B—H4B2	107.8
C4A—N4A—H4A1	120.0	C6A—C5A—C4A	121.1 (3)
C4A—N4A—H4A2	120.0	C6A—C5A—H5A	119.5
H4A1—N4A—H4A2	120.0	C4A—C5A—H5A	119.5
C6A—C1A—C2A	120.2 (3)	C1A—C6A—C5A	119.8 (3)
C6A—C1A—S1A	121.4 (2)	C1A—C6A—H6A	120.1
C2A—C1A—S1A	118.4 (2)	C5A—C6A—H6A	120.1
O1B—C1B—C2B	107.9 (8)	N2A—C7A—N3A	126.6 (2)
O1B—C1B—H1B1	110.1	N2A—C7A—N1A	119.2 (2)
C2B—C1B—H1B1	110.1	N3A—C7A—N1A	114.2 (2)
O1B—C1B—H1B2	110.1	O3A—C8A—H8A1	109.5
C2B—C1B—H1B2	110.1	O3A—C8A—H8A2	109.5
H1B1—C1B—H1B2	108.4	H8A1—C8A—H8A2	109.5
C3A—C2A—C1A	120.2 (3)	O3A—C8A—H8A3	109.5
C3A—C2A—H2A	119.9	H8A1—C8A—H8A3	109.5
C1A—C2A—H2A	119.9	H8A2—C8A—H8A3	109.5
C1B—C2B—O2B	113.3 (6)	N2A—C9A—C10A	122.9 (3)
C1B—C2B—H2B1	108.9	N2A—C9A—H9A	118.6
O2B—C2B—H2B1	108.9	C10A—C9A—H9A	118.6
C1B—C2B—H2B2	108.9	O3A—C10A—C11A	125.6 (3)
O2B—C2B—H2B2	108.9	O3A—C10A—C9A	117.9 (2)
H2B1—C2B—H2B2	107.7	C11A—C10A—C9A	116.4 (2)
C2A—C3A—C4A	120.7 (3)	N3A—C11A—C10A	121.7 (3)
C2A—C3A—H3A	119.7	N3A—C11A—H11A	119.1
C4A—C3A—H3A	119.7	C10A—C11A—H11A	119.1
C4B—C3B—O2B	109.7 (9)
O2A—S1A—N1A—C7A	54.6 (3)	N4A—C4A—C5A—C6A	−179.4 (3)
O1A—S1A—N1A—C7A	−178.3 (2)	C3A—C4A—C5A—C6A	0.7 (5)
C1A—S1A—N1A—C7A	−63.6 (3)	C2A—C1A—C6A—C5A	0.2 (4)
O2A—S1A—C1A—C6A	−14.4 (3)	S1A—C1A—C6A—C5A	179.1 (2)
O1A—S1A—C1A—C6A	−145.1 (2)	C4A—C5A—C6A—C1A	−0.7 (5)
N1A—S1A—C1A—C6A	104.0 (2)	C9A—N2A—C7A—N3A	0.1 (4)
O2A—S1A—C1A—C2A	164.5 (2)	C9A—N2A—C7A—N1A	−178.1 (3)
O1A—S1A—C1A—C2A	33.8 (3)	C11A—N3A—C7A—N2A	0.3 (4)
N1A—S1A—C1A—C2A	−77.0 (2)	C11A—N3A—C7A—N1A	178.5 (3)
C4B—O1B—C1B—C2B	−72.0 (9)	S1A—N1A—C7A—N2A	−15.5 (4)
C6A—C1A—C2A—C3A	0.2 (4)	S1A—N1A—C7A—N3A	166.1 (2)
S1A—C1A—C2A—C3A	−178.7 (2)	C7A—N2A—C9A—C10A	−1.0 (4)
O1B—C1B—C2B—O2B	55.4 (9)	C8A—O3A—C10A—C11A	−8.3 (5)
C3B—O2B—C2B—C1B	−40.4 (10)	C8A—O3A—C10A—C9A	172.5 (3)
C1A—C2A—C3A—C4A	−0.2 (5)	N2A—C9A—C10A—O3A	−179.3 (3)
C2B—O2B—C3B—C4B	38.2 (10)	N2A—C9A—C10A—C11A	1.4 (5)
C2A—C3A—C4A—N4A	179.9 (3)	C7A—N3A—C11A—C10A	0.2 (4)
C2A—C3A—C4A—C5A	−0.3 (5)	O3A—C10A—C11A—N3A	179.8 (3)
C1B—O1B—C4B—C3B	75.1 (11)	C9A—C10A—C11A—N3A	−1.0 (5)
O2B—C3B—C4B—O1B	−57.0 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A1···N2A^i	0.86	2.47	3.171 (4)	140
C3A—H3A···O2A^i	0.93	2.65	3.366 (4)	135
C6A—H6A···O1A^ii	0.93	2.63	3.397 (3)	141
C11A—H11A···O1A^iii	0.93	2.52	3.269 (4)	137
N1A—H1A···N3A^iii	0.81 (6)	2.12 (6)	2.907 (3)	165 (6)

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

(3) 4-Amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide tetrahydrofuran monosolvate

Crystal data

C11H12N4O3S·C4H8O	F(000) = 744
Mr = 352.42	Dx = 1.375 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9428 reflections
a = 8.0255 (2) Å	θ = 2.6–27.6°
b = 19.1956 (5) Å	µ = 0.22 mm^−1
c = 11.1829 (3) Å	T = 296 K
β = 98.886 (1)°	Needle, colourless
V = 1702.10 (8) Å^3	0.84 × 0.39 × 0.22 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	3442 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.6°, θmin = 2.1°
φ and ω scans	h = −10→9
14812 measured reflections	k = −24→24
3941 independent reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.5919P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.32 e Å^−3
3941 reflections	Δρmin = −0.41 e Å^−3
222 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.184 (7)

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.

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

	x	y	z	Uiso*/Ueq
S1A	0.51294 (4)	0.32593 (2)	0.44538 (3)	0.03343 (16)
O1A	0.49437 (16)	0.31307 (6)	0.56898 (10)	0.0451 (3)
O1B	0.2043 (4)	0.56777 (15)	0.1213 (2)	0.1185 (8)
O2A	0.63384 (15)	0.28586 (6)	0.39348 (12)	0.0455 (3)
O3A	0.65066 (19)	0.56565 (7)	0.05894 (11)	0.0532 (4)
N1A	0.56562 (18)	0.40877 (7)	0.44690 (12)	0.0364 (3)
N2A	0.62323 (17)	0.41662 (7)	0.24771 (12)	0.0379 (3)
N3A	0.56700 (18)	0.51673 (7)	0.35922 (12)	0.0382 (3)
N4A	−0.1622 (2)	0.29467 (10)	0.15651 (17)	0.0612 (5)
H4A1	−0.1754	0.2755	0.0862	0.073*
H4A2	−0.2486	0.3089	0.1865	0.073*
C1A	0.31649 (18)	0.31808 (7)	0.35542 (14)	0.0325 (3)
C1B	0.1347 (5)	0.50653 (19)	0.1723 (4)	0.1052 (11)
H1B1	0.2161	0.4688	0.1803	0.126*
H1B2	0.0336	0.4912	0.1200	0.126*
C2A	0.1738 (2)	0.34120 (9)	0.40179 (15)	0.0415 (4)
H2A	0.1860	0.3619	0.4778	0.050*
C2B	0.0949 (4)	0.52610 (17)	0.2911 (3)	0.0915 (9)
H2B1	0.1863	0.5135	0.3547	0.110*
H2B2	−0.0076	0.5033	0.3065	0.110*
C3A	0.0164 (2)	0.33342 (10)	0.33571 (17)	0.0461 (4)
H3A	−0.0777	0.3487	0.3674	0.055*
C3B	0.0717 (4)	0.60497 (16)	0.2845 (3)	0.0959 (10)
H3B1	−0.0450	0.6175	0.2861	0.115*
H3B2	0.1422	0.6277	0.3516	0.115*
C4A	−0.0041 (2)	0.30257 (9)	0.22052 (16)	0.0420 (4)
C4B	0.1237 (5)	0.6250 (2)	0.1675 (5)	0.1266 (15)
H4B1	0.0255	0.6386	0.1104	0.152*
H4B2	0.2003	0.6644	0.1794	0.152*
C5A	0.1399 (2)	0.28018 (9)	0.17505 (15)	0.0440 (4)
H5A	0.1286	0.2598	0.0988	0.053*
C6A	0.2986 (2)	0.28787 (8)	0.24179 (14)	0.0378 (3)
H6A	0.3932	0.2728	0.2105	0.045*
C7A	0.58489 (17)	0.44859 (8)	0.34544 (13)	0.0318 (3)
C8A	0.6192 (4)	0.63851 (10)	0.0603 (2)	0.0655 (6)
H8A1	0.6394	0.6587	−0.0147	0.098*
H8A2	0.6928	0.6596	0.1262	0.098*
H8A3	0.5040	0.6464	0.0703	0.098*
C9A	0.6451 (2)	0.45759 (9)	0.15547 (14)	0.0397 (3)
H9A	0.6729	0.4373	0.0857	0.048*
C10A	0.6282 (2)	0.52930 (9)	0.15925 (14)	0.0385 (3)
C11A	0.5887 (2)	0.55721 (8)	0.26475 (15)	0.0410 (4)
H11A	0.5767	0.6052	0.2708	0.049*
H1A	0.525 (3)	0.4323 (12)	0.500 (2)	0.051 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0367 (2)	0.0285 (2)	0.0361 (2)	0.00045 (13)	0.00886 (15)	0.00504 (13)
O1A	0.0574 (7)	0.0412 (6)	0.0372 (6)	−0.0031 (5)	0.0089 (5)	0.0108 (5)
O1B	0.132 (2)	0.113 (2)	0.1165 (19)	0.0079 (16)	0.0399 (16)	0.0007 (16)
O2A	0.0407 (6)	0.0369 (6)	0.0609 (7)	0.0076 (5)	0.0145 (5)	0.0028 (5)
O3A	0.0868 (10)	0.0399 (7)	0.0374 (6)	0.0010 (6)	0.0241 (6)	0.0068 (5)
N1A	0.0473 (7)	0.0307 (6)	0.0324 (6)	−0.0051 (5)	0.0099 (5)	0.0015 (5)
N2A	0.0469 (7)	0.0319 (6)	0.0360 (7)	−0.0003 (5)	0.0105 (5)	−0.0002 (5)
N3A	0.0502 (7)	0.0320 (6)	0.0346 (6)	−0.0016 (5)	0.0132 (5)	0.0008 (5)
N4A	0.0453 (8)	0.0672 (11)	0.0676 (11)	−0.0016 (8)	−0.0021 (7)	−0.0117 (9)
C1A	0.0346 (7)	0.0281 (7)	0.0366 (7)	−0.0010 (5)	0.0109 (6)	0.0011 (5)
C1B	0.107 (3)	0.087 (2)	0.117 (3)	−0.0079 (18)	0.003 (2)	−0.028 (2)
C2A	0.0413 (8)	0.0460 (9)	0.0394 (8)	0.0013 (7)	0.0135 (6)	−0.0074 (7)
C2B	0.0772 (17)	0.0830 (19)	0.108 (2)	−0.0051 (15)	−0.0070 (15)	0.0068 (18)
C3A	0.0368 (8)	0.0531 (10)	0.0509 (10)	0.0026 (7)	0.0149 (7)	−0.0053 (8)
C3B	0.098 (2)	0.0786 (19)	0.105 (2)	0.0078 (16)	−0.0036 (18)	−0.0216 (17)
C4A	0.0407 (8)	0.0367 (8)	0.0480 (9)	−0.0038 (6)	0.0052 (7)	0.0010 (7)
C4B	0.118 (3)	0.100 (3)	0.173 (4)	0.025 (2)	0.058 (3)	0.030 (3)
C5A	0.0525 (9)	0.0425 (9)	0.0380 (8)	−0.0027 (7)	0.0095 (7)	−0.0072 (7)
C6A	0.0422 (8)	0.0349 (8)	0.0392 (8)	0.0013 (6)	0.0158 (6)	−0.0034 (6)
C7A	0.0322 (7)	0.0320 (7)	0.0312 (7)	−0.0035 (5)	0.0055 (5)	0.0012 (5)
C8A	0.1106 (18)	0.0385 (10)	0.0513 (11)	−0.0015 (10)	0.0245 (11)	0.0107 (8)
C9A	0.0504 (9)	0.0377 (8)	0.0332 (7)	0.0003 (7)	0.0127 (6)	−0.0025 (6)
C10A	0.0470 (8)	0.0365 (8)	0.0332 (7)	−0.0012 (6)	0.0100 (6)	0.0037 (6)
C11A	0.0584 (10)	0.0303 (7)	0.0365 (8)	−0.0001 (7)	0.0144 (7)	0.0017 (6)

Geometric parameters (Å, º)

S1A—O2A	1.4296 (12)	C2A—H2A	0.9300
S1A—O1A	1.4344 (12)	C2B—C3B	1.526 (4)
S1A—N1A	1.6449 (13)	C2B—H2B1	0.9700
S1A—C1A	1.7408 (16)	C2B—H2B2	0.9700
O1B—C4B	1.413 (5)	C3A—C4A	1.404 (3)
O1B—C1B	1.455 (4)	C3A—H3A	0.9300
O3A—C10A	1.3566 (18)	C3B—C4B	1.484 (5)
O3A—C8A	1.422 (2)	C3B—H3B1	0.9700
N1A—C7A	1.3963 (18)	C3B—H3B2	0.9700
N1A—H1A	0.85 (2)	C4A—C5A	1.400 (2)
N2A—C9A	1.330 (2)	C4B—H4B1	0.9700
N2A—C7A	1.3303 (19)	C4B—H4B2	0.9700
N3A—C7A	1.327 (2)	C5A—C6A	1.381 (2)
N3A—C11A	1.344 (2)	C5A—H5A	0.9300
N4A—C4A	1.366 (2)	C6A—H6A	0.9300
N4A—H4A1	0.8600	C8A—H8A1	0.9600
N4A—H4A2	0.8600	C8A—H8A2	0.9600
C1A—C6A	1.384 (2)	C8A—H8A3	0.9600
C1A—C2A	1.400 (2)	C9A—C10A	1.385 (2)
C1B—C2B	1.464 (5)	C9A—H9A	0.9300
C1B—H1B1	0.9700	C10A—C11A	1.376 (2)
C1B—H1B2	0.9700	C11A—H11A	0.9300
C2A—C3A	1.369 (2)
O2A—S1A—O1A	118.47 (8)	C4B—C3B—H3B1	110.8
O2A—S1A—N1A	109.56 (7)	C2B—C3B—H3B1	110.8
O1A—S1A—N1A	102.78 (7)	C4B—C3B—H3B2	110.8
O2A—S1A—C1A	109.26 (8)	C2B—C3B—H3B2	110.8
O1A—S1A—C1A	108.81 (7)	H3B1—C3B—H3B2	108.9
N1A—S1A—C1A	107.34 (7)	N4A—C4A—C5A	121.86 (17)
C4B—O1B—C1B	105.1 (3)	N4A—C4A—C3A	119.69 (16)
C10A—O3A—C8A	116.77 (14)	C5A—C4A—C3A	118.45 (15)
C7A—N1A—S1A	125.55 (11)	O1B—C4B—C3B	109.1 (3)
C7A—N1A—H1A	112.2 (15)	O1B—C4B—H4B1	109.9
S1A—N1A—H1A	113.3 (15)	C3B—C4B—H4B1	109.9
C9A—N2A—C7A	116.06 (13)	O1B—C4B—H4B2	109.9
C7A—N3A—C11A	116.67 (13)	C3B—C4B—H4B2	109.9
C4A—N4A—H4A1	120.0	H4B1—C4B—H4B2	108.3
C4A—N4A—H4A2	120.0	C6A—C5A—C4A	120.99 (15)
H4A1—N4A—H4A2	120.0	C6A—C5A—H5A	119.5
C6A—C1A—C2A	119.88 (14)	C4A—C5A—H5A	119.5
C6A—C1A—S1A	121.53 (11)	C5A—C6A—C1A	119.80 (14)
C2A—C1A—S1A	118.56 (12)	C5A—C6A—H6A	120.1
O1B—C1B—C2B	107.4 (3)	C1A—C6A—H6A	120.1
O1B—C1B—H1B1	110.2	N3A—C7A—N2A	126.36 (13)
C2B—C1B—H1B1	110.2	N3A—C7A—N1A	114.68 (13)
O1B—C1B—H1B2	110.2	N2A—C7A—N1A	118.93 (13)
C2B—C1B—H1B2	110.2	O3A—C8A—H8A1	109.5
H1B1—C1B—H1B2	108.5	O3A—C8A—H8A2	109.5
C3A—C2A—C1A	120.30 (15)	H8A1—C8A—H8A2	109.5
C3A—C2A—H2A	119.9	O3A—C8A—H8A3	109.5
C1A—C2A—H2A	119.9	H8A1—C8A—H8A3	109.5
C1B—C2B—C3B	104.6 (3)	H8A2—C8A—H8A3	109.5
C1B—C2B—H2B1	110.8	N2A—C9A—C10A	122.61 (14)
C3B—C2B—H2B1	110.8	N2A—C9A—H9A	118.7
C1B—C2B—H2B2	110.8	C10A—C9A—H9A	118.7
C3B—C2B—H2B2	110.8	O3A—C10A—C11A	125.89 (15)
H2B1—C2B—H2B2	108.9	O3A—C10A—C9A	117.38 (14)
C2A—C3A—C4A	120.57 (15)	C11A—C10A—C9A	116.73 (14)
C2A—C3A—H3A	119.7	N3A—C11A—C10A	121.57 (15)
C4A—C3A—H3A	119.7	N3A—C11A—H11A	119.2
C4B—C3B—C2B	104.5 (3)	C10A—C11A—H11A	119.2
O2A—S1A—N1A—C7A	58.79 (15)	N4A—C4A—C5A—C6A	−179.20 (17)
O1A—S1A—N1A—C7A	−174.39 (13)	C3A—C4A—C5A—C6A	0.3 (3)
C1A—S1A—N1A—C7A	−59.74 (15)	C4A—C5A—C6A—C1A	0.0 (3)
O2A—S1A—C1A—C6A	−10.92 (15)	C2A—C1A—C6A—C5A	−0.5 (2)
O1A—S1A—C1A—C6A	−141.65 (13)	S1A—C1A—C6A—C5A	177.52 (12)
N1A—S1A—C1A—C6A	107.80 (13)	C11A—N3A—C7A—N2A	0.5 (2)
O2A—S1A—C1A—C2A	167.13 (12)	C11A—N3A—C7A—N1A	178.40 (14)
O1A—S1A—C1A—C2A	36.40 (14)	C9A—N2A—C7A—N3A	−0.1 (2)
N1A—S1A—C1A—C2A	−74.15 (14)	C9A—N2A—C7A—N1A	−177.96 (14)
C4B—O1B—C1B—C2B	−31.4 (4)	S1A—N1A—C7A—N3A	156.66 (12)
C6A—C1A—C2A—C3A	0.7 (2)	S1A—N1A—C7A—N2A	−25.3 (2)
S1A—C1A—C2A—C3A	−177.43 (14)	C7A—N2A—C9A—C10A	−0.5 (2)
O1B—C1B—C2B—C3B	23.8 (4)	C8A—O3A—C10A—C11A	−4.6 (3)
C1A—C2A—C3A—C4A	−0.3 (3)	C8A—O3A—C10A—C9A	174.92 (18)
C1B—C2B—C3B—C4B	−7.6 (4)	N2A—C9A—C10A—O3A	−178.91 (15)
C2A—C3A—C4A—N4A	179.37 (17)	N2A—C9A—C10A—C11A	0.6 (3)
C2A—C3A—C4A—C5A	−0.1 (3)	C7A—N3A—C11A—C10A	−0.3 (2)
C1B—O1B—C4B—C3B	26.4 (4)	O3A—C10A—C11A—N3A	179.25 (16)
C2B—C3B—C4B—O1B	−11.7 (4)	C9A—C10A—C11A—N3A	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A2···N2A^i	0.86	2.45	3.167 (2)	141
C6A—H6A···O1A^ii	0.93	2.51	3.3007 (19)	144
C9A—H9A···O1B^iii	0.93	2.65	3.526 (3)	156
C11A—H11A···O1A^iv	0.93	2.51	3.238 (2)	135
N1A—H1A···N3A^iv	0.85 (2)	2.09 (2)	2.9312 (19)	175 (2)

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