Sulfonate salts of the therapeutic agent dapsone: 4-[(4-amino­phen­yl)sulfon­yl]anilinium benzene­sulfonate monohydrate and 4-[(4-amino­phen­yl)sulfon­yl]anilinium methane­sulfonate monohydrate

Dapsone, formerly used to treat leprosy, now has wider therapeutic applications. As is the case for many therapeutic agents, low aqueous solubility and high toxicity are the main problems associated with its use. Derivatization of its amino groups has been widely explored but shows no significant therapeutic improvements. Cocrystals have been prepared to understand not only its structural properties, but also its solubility and dissolution rate. Few salts of dapsone have been described. The title salts, C₁₂H₁₃N₂O₂S⁺·C₆H₅O₃S⁻·H₂O and C₁₂H₁₃N₂O₂S⁺·CH₃SO₃⁻·H₂O, crystallize as hydrates and both compounds exhibit the same space group (monoclinic, P2₁/n). The asymmetric unit of each salt consists of a 4-[(4-amino­phen­yl)sulfon­yl]anilinium monocation, the corresponding sulfonate anion and a water mol­ecule. The cation, anion and water mol­ecule form hydrogen-bonded networks through N—H...O=S, N—H...O_water and O_water—H...O=S hydrogen bonds. For both salts, the water mol­ecules inter­act with one sulfonate anion and two anilinium cations. The benzene­sulfonate salt forms a two-dimensional network, while the hydrogen bonding within the methane­sulfonate salt results in a three-dimensional network.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b). Molecular graphics: XP (Bruker, 2012) and DIAMOND (Brandenburg, 2006) for (I); XP (Bruker, 2012) for (II). Software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010) for (I); SHELXL2014 (Sheldrick, 2015b) for (II).

(I) 4-[(4-Aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate

Crystal data

C12H13N2O2S^+·C6H5O3S^−·H2O	F(000) = 888
Mr = 424.48	Dx = 1.502 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.7220 (15) Å	Cell parameters from 9553 reflections
b = 6.1383 (6) Å	θ = 2.6–25.3°
c = 19.5185 (19) Å	µ = 0.32 mm^−1
β = 94.954 (2)°	T = 150 K
V = 1876.6 (3) Å^3	Prism, colourless
Z = 4	0.26 × 0.25 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2988 reflections with I > 2σ(I)
Detector resolution: 0.83 pixels mm^-1	Rint = 0.031
φ and ω scans	θmax = 25.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −18→18
Tmin = 0.673, Tmax = 0.745	k = −7→7
15097 measured reflections	l = −22→23
3415 independent reflections

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)] = 0.032	Hydrogen site location: mixed
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 1.4352P] where P = (Fo^2 + 2Fc^2)/3
3415 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.30 e Å^−3
5 restraints	Δρmin = −0.38 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.36176 (3)	1.12648 (7)	0.61045 (2)	0.01840 (13)
O1	0.35572 (8)	1.3614 (2)	0.60690 (7)	0.0232 (3)
O2	0.43349 (8)	1.0307 (2)	0.65042 (6)	0.0250 (3)
N1	0.04211 (12)	0.7856 (3)	0.70463 (10)	0.0315 (4)
H1A	−0.0042 (10)	0.870 (3)	0.7059 (12)	0.038*
H1B	0.0409 (15)	0.653 (2)	0.7233 (11)	0.038*
N2	0.37629 (10)	0.8011 (3)	0.32344 (8)	0.0175 (3)
H2A	0.3976 (12)	0.904 (3)	0.2968 (9)	0.021*
H2B	0.4103 (11)	0.683 (2)	0.3239 (10)	0.021*
H2C	0.3241 (8)	0.760 (3)	0.3056 (10)	0.021*
C1	0.26819 (11)	1.0274 (3)	0.64051 (9)	0.0183 (4)
C2	0.19666 (12)	1.1609 (3)	0.63938 (9)	0.0201 (4)
H2	0.1993	1.3057	0.6225	0.024*
C3	0.12210 (12)	1.0843 (3)	0.66261 (9)	0.0225 (4)
H3	0.0737	1.1771	0.6622	0.027*
C4	0.11710 (12)	0.8688 (3)	0.68700 (9)	0.0220 (4)
C5	0.19108 (13)	0.7398 (3)	0.69036 (9)	0.0235 (4)
H5	0.1898	0.5972	0.7092	0.028*
S2	0.36767 (3)	0.24821 (7)	0.19887 (2)	0.01704 (12)
O3	0.37327 (8)	0.4831 (2)	0.20388 (6)	0.0240 (3)
O4	0.28668 (8)	0.1575 (2)	0.21546 (7)	0.0259 (3)
O5	0.43860 (8)	0.1384 (2)	0.23886 (6)	0.0199 (3)
C13	0.37871 (11)	0.1824 (3)	0.11178 (9)	0.0188 (4)
C14	0.40305 (14)	0.3415 (3)	0.06753 (10)	0.0282 (5)
H14	0.4130	0.4863	0.0834	0.034*
C15	0.41290 (15)	0.2880 (3)	−0.00047 (10)	0.0333 (5)
H15	0.4295	0.3967	−0.0313	0.040*
C16	0.39865 (13)	0.0782 (3)	−0.02336 (10)	0.0288 (5)
H16	0.4059	0.0419	−0.0698	0.035*
C17	0.37379 (14)	−0.0796 (3)	0.02123 (10)	0.0307 (5)
H17	0.3633	−0.2240	0.0051	0.037*
C18	0.36397 (13)	−0.0290 (3)	0.08912 (10)	0.0260 (4)
H18	0.3473	−0.1380	0.1198	0.031*
O6	0.48686 (9)	0.4437 (2)	0.34436 (7)	0.0244 (3)
H6A	0.4837 (14)	0.341 (4)	0.3143 (12)	0.029*
H6B	0.5390 (15)	0.485 (4)	0.3483 (11)	0.029*
C6	0.26540 (12)	0.8166 (3)	0.66683 (9)	0.0218 (4)
H6	0.3146	0.7264	0.6685	0.026*
C7	0.36412 (11)	1.0307 (3)	0.52505 (9)	0.0177 (4)
C8	0.40077 (14)	0.8312 (3)	0.51438 (10)	0.0297 (5)
H8	0.4237	0.7466	0.5524	0.036*
C9	0.40397 (14)	0.7546 (3)	0.44791 (10)	0.0288 (5)
H9	0.4285	0.6165	0.4399	0.035*
C10	0.37120 (11)	0.8809 (3)	0.39354 (9)	0.0171 (4)
C11	0.33454 (12)	1.0802 (3)	0.40377 (10)	0.0254 (4)
H11	0.3117	1.1644	0.3657	0.030*
C12	0.33132 (12)	1.1571 (3)	0.47019 (10)	0.0249 (4)
H12	0.3068	1.2954	0.4781	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0191 (2)	0.0199 (2)	0.0158 (2)	0.00194 (17)	−0.00057 (17)	−0.00304 (17)
O1	0.0252 (7)	0.0193 (7)	0.0249 (7)	−0.0008 (5)	0.0012 (6)	−0.0044 (5)
O2	0.0221 (7)	0.0321 (8)	0.0198 (7)	0.0058 (6)	−0.0045 (5)	−0.0039 (6)
N1	0.0317 (10)	0.0286 (10)	0.0359 (10)	0.0010 (8)	0.0127 (8)	0.0083 (8)
N2	0.0189 (8)	0.0195 (8)	0.0143 (8)	0.0001 (6)	0.0023 (6)	−0.0005 (6)
C1	0.0226 (9)	0.0204 (9)	0.0116 (8)	0.0025 (7)	0.0004 (7)	−0.0024 (7)
C2	0.0251 (10)	0.0182 (9)	0.0165 (9)	0.0029 (8)	−0.0003 (7)	0.0001 (7)
C3	0.0244 (10)	0.0234 (9)	0.0198 (9)	0.0054 (8)	0.0021 (8)	0.0003 (8)
C4	0.0290 (10)	0.0247 (10)	0.0127 (9)	0.0000 (8)	0.0045 (7)	−0.0016 (7)
C5	0.0359 (11)	0.0176 (9)	0.0174 (9)	0.0036 (8)	0.0043 (8)	0.0014 (7)
S2	0.0176 (2)	0.0179 (2)	0.0156 (2)	0.00094 (17)	0.00079 (17)	0.00131 (17)
O3	0.0313 (7)	0.0184 (7)	0.0227 (7)	0.0026 (6)	0.0038 (6)	−0.0013 (5)
O4	0.0192 (7)	0.0319 (8)	0.0271 (7)	−0.0005 (6)	0.0045 (6)	0.0063 (6)
O5	0.0201 (7)	0.0219 (7)	0.0173 (6)	0.0032 (5)	−0.0016 (5)	−0.0004 (5)
C13	0.0186 (9)	0.0216 (9)	0.0156 (9)	−0.0006 (7)	−0.0020 (7)	0.0008 (7)
C14	0.0439 (12)	0.0190 (10)	0.0216 (10)	−0.0053 (9)	0.0020 (9)	0.0013 (8)
C15	0.0522 (14)	0.0289 (11)	0.0189 (10)	−0.0093 (10)	0.0027 (9)	0.0045 (8)
C16	0.0371 (12)	0.0337 (11)	0.0149 (9)	−0.0021 (9)	−0.0007 (8)	−0.0022 (8)
C17	0.0444 (13)	0.0231 (10)	0.0238 (11)	−0.0043 (9)	−0.0016 (9)	−0.0048 (8)
C18	0.0361 (11)	0.0219 (10)	0.0197 (10)	−0.0068 (8)	0.0005 (8)	0.0027 (8)
O6	0.0251 (7)	0.0221 (7)	0.0252 (7)	0.0003 (6)	−0.0018 (6)	−0.0068 (6)
C6	0.0277 (10)	0.0199 (9)	0.0178 (9)	0.0079 (8)	0.0015 (8)	−0.0019 (8)
C7	0.0182 (9)	0.0200 (9)	0.0152 (9)	−0.0008 (7)	0.0025 (7)	−0.0012 (7)
C8	0.0470 (13)	0.0257 (10)	0.0164 (10)	0.0129 (9)	0.0022 (9)	0.0036 (8)
C9	0.0470 (13)	0.0198 (10)	0.0200 (10)	0.0111 (9)	0.0056 (9)	0.0008 (8)
C10	0.0166 (9)	0.0198 (9)	0.0154 (9)	−0.0036 (7)	0.0040 (7)	−0.0013 (7)
C11	0.0291 (10)	0.0276 (10)	0.0191 (10)	0.0084 (8)	−0.0002 (8)	0.0036 (8)
C12	0.0293 (11)	0.0227 (10)	0.0228 (10)	0.0090 (8)	0.0027 (8)	−0.0011 (8)

Geometric parameters (Å, º)

S1—O2	1.4401 (13)	C13—C14	1.380 (3)
S1—O1	1.4467 (13)	C13—C18	1.384 (3)
S1—C1	1.7399 (19)	C14—C15	1.389 (3)
S1—C7	1.7710 (18)	C14—H14	0.9500
N1—C4	1.356 (3)	C15—C16	1.375 (3)
N1—H1A	0.896 (10)	C15—H15	0.9500
N1—H1B	0.894 (10)	C16—C17	1.381 (3)
N2—C10	1.462 (2)	C16—H16	0.9500
N2—H2A	0.901 (9)	C17—C18	1.383 (3)
N2—H2B	0.901 (9)	C17—H17	0.9500
N2—H2C	0.900 (9)	C18—H18	0.9500
C1—C2	1.390 (2)	O6—H6A	0.86 (2)
C1—C6	1.394 (3)	O6—H6B	0.86 (2)
C2—C3	1.376 (3)	C6—H6	0.9500
C2—H2	0.9500	C7—C8	1.377 (3)
C3—C4	1.411 (3)	C7—C12	1.386 (3)
C3—H3	0.9500	C8—C9	1.385 (3)
C4—C5	1.404 (3)	C8—H8	0.9500
C5—C6	1.375 (3)	C9—C10	1.377 (3)
C5—H5	0.9500	C9—H9	0.9500
S2—O3	1.4474 (13)	C10—C11	1.375 (3)
S2—O4	1.4517 (13)	C11—C12	1.385 (3)
S2—O5	1.4685 (13)	C11—H11	0.9500
S2—C13	1.7704 (18)	C12—H12	0.9500
O2—S1—O1	118.54 (8)	C18—C13—S2	119.56 (14)
O2—S1—C1	108.67 (8)	C13—C14—C15	119.39 (18)
O1—S1—C1	108.10 (8)	C13—C14—H14	120.3
O2—S1—C7	107.18 (8)	C15—C14—H14	120.3
O1—S1—C7	107.01 (8)	C16—C15—C14	120.23 (19)
C1—S1—C7	106.77 (8)	C16—C15—H15	119.9
C4—N1—H1A	121.1 (15)	C14—C15—H15	119.9
C4—N1—H1B	119.7 (15)	C15—C16—C17	119.95 (18)
H1A—N1—H1B	118 (2)	C15—C16—H16	120.0
C10—N2—H2A	111.0 (13)	C17—C16—H16	120.0
C10—N2—H2B	109.9 (13)	C16—C17—C18	120.50 (19)
H2A—N2—H2B	108.6 (18)	C16—C17—H17	119.8
C10—N2—H2C	109.5 (13)	C18—C17—H17	119.8
H2A—N2—H2C	110.3 (18)	C17—C18—C13	119.17 (18)
H2B—N2—H2C	107.4 (18)	C17—C18—H18	120.4
C2—C1—C6	120.11 (17)	C13—C18—H18	120.4
C2—C1—S1	119.68 (14)	H6A—O6—H6B	106 (2)
C6—C1—S1	120.20 (14)	C5—C6—C1	119.73 (17)
C3—C2—C1	120.30 (17)	C5—C6—H6	120.1
C3—C2—H2	119.8	C1—C6—H6	120.1
C1—C2—H2	119.8	C8—C7—C12	120.94 (17)
C2—C3—C4	120.37 (17)	C8—C7—S1	118.74 (14)
C2—C3—H3	119.8	C12—C7—S1	120.31 (14)
C4—C3—H3	119.8	C7—C8—C9	119.53 (18)
N1—C4—C5	120.72 (18)	C7—C8—H8	120.2
N1—C4—C3	120.91 (18)	C9—C8—H8	120.2
C5—C4—C3	118.34 (17)	C10—C9—C8	119.31 (18)
C6—C5—C4	121.02 (17)	C10—C9—H9	120.3
C6—C5—H5	119.5	C8—C9—H9	120.3
C4—C5—H5	119.5	C11—C10—C9	121.50 (17)
O3—S2—O4	114.61 (8)	C11—C10—N2	119.44 (16)
O3—S2—O5	112.48 (8)	C9—C10—N2	119.06 (16)
O4—S2—O5	110.23 (8)	C10—C11—C12	119.28 (17)
O3—S2—C13	106.37 (8)	C10—C11—H11	120.4
O4—S2—C13	106.68 (8)	C12—C11—H11	120.4
O5—S2—C13	105.82 (8)	C11—C12—C7	119.43 (17)
C14—C13—C18	120.77 (18)	C11—C12—H12	120.3
C14—C13—S2	119.66 (15)	C7—C12—H12	120.3
O2—S1—C1—C2	146.36 (14)	C15—C16—C17—C18	−0.7 (3)
O1—S1—C1—C2	16.49 (17)	C16—C17—C18—C13	0.5 (3)
C7—S1—C1—C2	−98.34 (15)	C14—C13—C18—C17	−0.1 (3)
O2—S1—C1—C6	−32.42 (17)	S2—C13—C18—C17	−179.19 (16)
O1—S1—C1—C6	−162.29 (14)	C4—C5—C6—C1	1.4 (3)
C7—S1—C1—C6	82.88 (16)	C2—C1—C6—C5	1.3 (3)
C6—C1—C2—C3	−1.6 (3)	S1—C1—C6—C5	−179.89 (14)
S1—C1—C2—C3	179.62 (14)	O2—S1—C7—C8	27.76 (18)
C1—C2—C3—C4	−0.8 (3)	O1—S1—C7—C8	155.90 (16)
C2—C3—C4—N1	−174.45 (18)	C1—S1—C7—C8	−88.53 (17)
C2—C3—C4—C5	3.4 (3)	O2—S1—C7—C12	−150.82 (15)
N1—C4—C5—C6	174.17 (18)	O1—S1—C7—C12	−22.68 (18)
C3—C4—C5—C6	−3.7 (3)	C1—S1—C7—C12	92.89 (17)
O3—S2—C13—C14	9.99 (18)	C12—C7—C8—C9	−0.8 (3)
O4—S2—C13—C14	132.76 (16)	S1—C7—C8—C9	−179.34 (17)
O5—S2—C13—C14	−109.84 (16)	C7—C8—C9—C10	0.7 (3)
O3—S2—C13—C18	−170.92 (15)	C8—C9—C10—C11	−0.7 (3)
O4—S2—C13—C18	−48.15 (17)	C8—C9—C10—N2	178.80 (18)
O5—S2—C13—C18	69.25 (17)	C9—C10—C11—C12	0.7 (3)
C18—C13—C14—C15	−0.1 (3)	N2—C10—C11—C12	−178.76 (17)
S2—C13—C14—C15	178.99 (16)	C10—C11—C12—C7	−0.8 (3)
C13—C14—C15—C16	−0.1 (3)	C8—C7—C12—C11	0.8 (3)
C14—C15—C16—C17	0.5 (3)	S1—C7—C12—C11	179.36 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.90 (1)	2.12 (1)	3.009 (2)	170 (2)
N1—H1B···O2^ii	0.89 (1)	2.57 (2)	3.227 (2)	131 (2)
N1—H1B···O5^iii	0.89 (1)	2.44 (2)	3.171 (2)	139 (2)
N2—H2A···O5^iv	0.90 (1)	1.97 (1)	2.872 (2)	177 (2)
N2—H2B···O6	0.90 (1)	1.92 (1)	2.807 (2)	168 (2)
N2—H2C···O4^v	0.90 (1)	1.86 (1)	2.754 (2)	170 (2)
O6—H6A···O5	0.86 (2)	2.01 (2)	2.8388 (19)	162 (2)
O6—H6B···O1^vi	0.86 (2)	2.03 (2)	2.838 (2)	156 (2)

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) x, y+1, z; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x+1, −y+2, −z+1.

(II) 4-[(4-Aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate

Crystal data

C12H13N2O2S^+·CH3O3S^−·H2O	F(000) = 760
Mr = 362.41	Dx = 1.478 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.9355 (8) Å	Cell parameters from 9991 reflections
b = 6.0062 (3) Å	θ = 2.4–25.3°
c = 17.1547 (9) Å	µ = 0.36 mm^−1
β = 97.222 (2)°	T = 296 K
V = 1628.88 (14) Å^3	Prism, colourless
Z = 4	0.32 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2206 reflections with I > 2σ(I)
Radiation source: fine-focus, sealed tube	Rint = 0.110
Detector resolution: 0.83 pixels mm^-1	θmax = 25.3°, θmin = 2.4°
φ and ω scans	h = −19→18
19504 measured reflections	k = −6→7
2952 independent reflections	l = −20→20

Refinement

Refinement on F^2	7 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) = 0.109	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 0.642P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2952 reflections	Δρmax = 0.28 e Å^−3
230 parameters	Δρmin = −0.26 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.85447 (4)	1.13041 (10)	0.62161 (3)	0.03803 (19)
O1	0.85110 (11)	1.3704 (3)	0.61993 (10)	0.0468 (4)
O2	0.91640 (11)	1.0241 (3)	0.67735 (9)	0.0512 (5)
N1	0.88462 (14)	0.8006 (4)	0.29929 (12)	0.0385 (5)
H1A	0.8318 (8)	0.747 (4)	0.2873 (14)	0.046*
H1B	0.9215 (13)	0.688 (3)	0.2974 (14)	0.046*
H1C	0.8960 (16)	0.904 (3)	0.2640 (11)	0.046*
N2	0.51378 (18)	0.7706 (4)	0.63642 (18)	0.0698 (8)
H2A	0.511 (2)	0.635 (3)	0.6564 (18)	0.084*
H2B	0.4711 (15)	0.868 (4)	0.635 (2)	0.084*
C1	0.87100 (13)	1.0412 (4)	0.52667 (12)	0.0327 (5)
C2	0.90914 (16)	0.8385 (4)	0.51728 (13)	0.0395 (6)
H2	0.9303	0.7541	0.5608	0.047*
C3	0.91540 (15)	0.7627 (4)	0.44215 (13)	0.0377 (6)
H3	0.9406	0.6260	0.4347	0.045*
C4	0.88431 (14)	0.8902 (4)	0.37850 (12)	0.0321 (5)
C5	0.84819 (15)	1.0940 (4)	0.38763 (13)	0.0388 (6)
H5	0.8283	1.1793	0.3440	0.047*
C6	0.84170 (15)	1.1707 (4)	0.46201 (14)	0.0402 (6)
H6	0.8177	1.3093	0.4690	0.048*
C7	0.75397 (15)	1.0310 (4)	0.63248 (13)	0.0373 (6)
C8	0.74368 (18)	0.8187 (4)	0.66248 (14)	0.0451 (6)
H8	0.7908	0.7336	0.6807	0.054*
C9	0.66471 (19)	0.7360 (4)	0.66516 (15)	0.0481 (7)
H9	0.6585	0.5942	0.6854	0.058*
C10	0.59271 (17)	0.8593 (4)	0.63812 (15)	0.0478 (7)
C11	0.60420 (17)	1.0742 (4)	0.60991 (17)	0.0544 (7)
H11	0.5573	1.1621	0.5933	0.065*
C12	0.68326 (16)	1.1560 (4)	0.60646 (15)	0.0456 (6)
H12	0.6898	1.2978	0.5863	0.055*
S2	0.65067 (4)	0.73427 (10)	0.34536 (3)	0.0397 (2)
O3	0.64875 (13)	0.9733 (3)	0.34501 (12)	0.0672 (6)
O4	0.57165 (10)	0.6382 (3)	0.30678 (9)	0.0442 (4)
O5	0.72214 (12)	0.6393 (3)	0.31340 (11)	0.0629 (6)
C13	0.6592 (2)	0.6486 (6)	0.44346 (16)	0.0765 (10)
H13A	0.7108	0.7056	0.4714	0.115*
H13B	0.6597	0.4889	0.4458	0.115*
H13C	0.6119	0.7042	0.4671	0.115*
O6	0.50636 (12)	0.9451 (3)	0.18867 (11)	0.0509 (5)
H6A	0.5101 (18)	0.845 (3)	0.2237 (12)	0.061*
H6B	0.4541 (8)	0.975 (5)	0.1863 (16)	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0376 (4)	0.0400 (4)	0.0364 (3)	0.0024 (3)	0.0041 (3)	−0.0063 (3)
O1	0.0468 (11)	0.0379 (10)	0.0562 (11)	−0.0043 (8)	0.0084 (9)	−0.0127 (8)
O2	0.0492 (11)	0.0670 (12)	0.0355 (9)	0.0149 (9)	−0.0014 (8)	−0.0068 (8)
N1	0.0403 (13)	0.0402 (12)	0.0350 (11)	0.0028 (9)	0.0053 (10)	−0.0005 (9)
N2	0.0586 (17)	0.0571 (17)	0.100 (2)	−0.0133 (13)	0.0330 (16)	0.0027 (15)
C1	0.0295 (12)	0.0341 (13)	0.0350 (12)	−0.0022 (10)	0.0063 (10)	−0.0009 (10)
C2	0.0447 (15)	0.0407 (13)	0.0332 (12)	0.0058 (11)	0.0052 (11)	0.0066 (11)
C3	0.0443 (15)	0.0326 (13)	0.0369 (13)	0.0067 (11)	0.0080 (11)	0.0015 (10)
C4	0.0311 (12)	0.0349 (13)	0.0310 (12)	−0.0036 (10)	0.0061 (10)	−0.0021 (10)
C5	0.0416 (14)	0.0389 (14)	0.0356 (13)	0.0036 (11)	0.0036 (11)	0.0054 (10)
C6	0.0410 (15)	0.0336 (13)	0.0465 (14)	0.0063 (11)	0.0073 (12)	0.0010 (11)
C7	0.0440 (14)	0.0352 (13)	0.0344 (12)	0.0037 (11)	0.0114 (11)	−0.0019 (10)
C8	0.0605 (18)	0.0376 (14)	0.0401 (14)	0.0106 (12)	0.0177 (13)	0.0041 (11)
C9	0.071 (2)	0.0326 (14)	0.0463 (15)	−0.0008 (13)	0.0288 (14)	0.0041 (11)
C10	0.0542 (18)	0.0425 (15)	0.0512 (16)	−0.0047 (13)	0.0250 (14)	−0.0050 (12)
C11	0.0415 (16)	0.0487 (16)	0.0751 (19)	0.0051 (13)	0.0155 (14)	0.0112 (14)
C12	0.0470 (16)	0.0334 (13)	0.0582 (16)	0.0025 (12)	0.0134 (13)	0.0093 (12)
S2	0.0364 (4)	0.0448 (4)	0.0370 (3)	−0.0044 (3)	0.0010 (3)	−0.0028 (3)
O3	0.0620 (13)	0.0455 (12)	0.0893 (14)	−0.0093 (9)	−0.0088 (11)	−0.0048 (10)
O4	0.0385 (10)	0.0451 (10)	0.0466 (10)	−0.0101 (8)	−0.0041 (8)	0.0036 (8)
O5	0.0432 (11)	0.0833 (15)	0.0640 (12)	−0.0059 (10)	0.0135 (10)	−0.0222 (11)
C13	0.076 (2)	0.113 (3)	0.0372 (16)	0.013 (2)	−0.0027 (15)	0.0078 (17)
O6	0.0471 (11)	0.0443 (11)	0.0593 (12)	−0.0022 (9)	−0.0009 (10)	0.0129 (9)

Geometric parameters (Å, º)

S1—O2	1.4347 (18)	C6—H6	0.9300
S1—O1	1.4428 (17)	C7—C12	1.381 (3)
S1—C7	1.741 (2)	C7—C8	1.392 (3)
S1—C1	1.765 (2)	C8—C9	1.359 (4)
N1—C4	1.462 (3)	C8—H8	0.9300
N1—H1A	0.900 (10)	C9—C10	1.395 (4)
N1—H1B	0.901 (10)	C9—H9	0.9300
N1—H1C	0.903 (10)	C10—C11	1.398 (3)
N2—C10	1.363 (4)	C11—C12	1.360 (4)
N2—H2A	0.888 (10)	C11—H11	0.9300
N2—H2B	0.895 (10)	C12—H12	0.9300
C1—C2	1.379 (3)	S2—O3	1.436 (2)
C1—C6	1.387 (3)	S2—O5	1.4423 (19)
C2—C3	1.382 (3)	S2—O4	1.4653 (17)
C2—H2	0.9300	S2—C13	1.749 (3)
C3—C4	1.374 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.370 (3)	C13—H13C	0.9600
C5—C6	1.373 (3)	O6—H6A	0.848 (10)
C5—H5	0.9300	O6—H6B	0.848 (10)
O2—S1—O1	118.60 (11)	C1—C6—H6	120.1
O2—S1—C7	109.93 (11)	C12—C7—C8	119.2 (2)
O1—S1—C7	108.21 (11)	C12—C7—S1	120.20 (18)
O2—S1—C1	108.05 (10)	C8—C7—S1	120.43 (19)
O1—S1—C1	107.11 (10)	C9—C8—C7	120.0 (2)
C7—S1—C1	103.93 (10)	C9—C8—H8	120.0
C4—N1—H1A	103.4 (16)	C7—C8—H8	120.0
C4—N1—H1B	112.8 (16)	C8—C9—C10	121.4 (2)
H1A—N1—H1B	109 (2)	C8—C9—H9	119.3
C4—N1—H1C	113.1 (16)	C10—C9—H9	119.3
H1A—N1—H1C	111 (2)	N2—C10—C9	121.2 (2)
H1B—N1—H1C	108 (2)	N2—C10—C11	120.9 (3)
C10—N2—H2A	116 (2)	C9—C10—C11	117.8 (2)
C10—N2—H2B	116 (2)	C12—C11—C10	120.7 (3)
H2A—N2—H2B	123 (3)	C12—C11—H11	119.7
C2—C1—C6	120.7 (2)	C10—C11—H11	119.7
C2—C1—S1	119.64 (17)	C11—C12—C7	120.8 (2)
C6—C1—S1	119.56 (17)	C11—C12—H12	119.6
C1—C2—C3	119.0 (2)	C7—C12—H12	119.6
C1—C2—H2	120.5	O3—S2—O5	114.29 (12)
C3—C2—H2	120.5	O3—S2—O4	112.04 (11)
C4—C3—C2	119.8 (2)	O5—S2—O4	110.33 (11)
C4—C3—H3	120.1	O3—S2—C13	107.30 (16)
C2—C3—H3	120.1	O5—S2—C13	106.23 (15)
C5—C4—C3	121.4 (2)	O4—S2—C13	106.10 (14)
C5—C4—N1	119.0 (2)	S2—C13—H13A	109.5
C3—C4—N1	119.4 (2)	S2—C13—H13B	109.5
C4—C5—C6	119.2 (2)	H13A—C13—H13B	109.5
C4—C5—H5	120.4	S2—C13—H13C	109.5
C6—C5—H5	120.4	H13A—C13—H13C	109.5
C5—C6—C1	119.9 (2)	H13B—C13—H13C	109.5
C5—C6—H6	120.1	H6A—O6—H6B	100 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.90 (1)	1.97 (1)	2.804 (3)	154 (2)
N1—H1B···O6^i	0.90 (1)	1.85 (1)	2.744 (3)	170 (2)
N1—H1C···O4^ii	0.90 (1)	1.97 (1)	2.868 (3)	175 (2)
N1—H1C···O5^ii	0.90 (1)	2.58 (2)	3.153 (3)	122 (2)
N2—H2A···O4^iii	0.89 (1)	2.24 (2)	3.027 (3)	147 (3)
N2—H2B···O3^iv	0.90 (1)	2.20 (2)	3.063 (3)	162 (3)
O6—H6A···O4	0.85 (1)	2.04 (2)	2.838 (2)	156 (3)
O6—H6B···O1^v	0.85 (1)	2.09 (2)	2.829 (3)	145 (3)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) x−1/2, −y+5/2, z−1/2.