Crystal structure of methyl 2-hy-droxy-5-[(4-oxo-4,5-di-hydro-1,3-thia-zol-2-yl)amino]benzoate.

The title compound, C11H10N2O4S, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. They differ primarily in the rotational orientation of the five-membered heterocyclic ring. In mol-ecule A this ring is inclined to the benzene ring by 48.17 (8)°, while in mol-ecule B the same dihedral angle is 23.07 (8)°. In each mol-ecule there is an intra-molecular O-H⋯O hydrogen bond involving the adjacent hydroxyl group and the ester carbonyl O atom. In the crystal, the A mol-ecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers. These dimers are linked to the B mol-ecules via N-H.·O, C-H⋯O and C-H⋯S hydrogen bonds forming corrugated sheets lying parallel to (102).

Related literature

For pharmaceutical and chemotherapeutic properties of amino salicylic acid derivatives, see: Abdel-Alim et al. (2005 ▸); Abdu-Allah et al. (2005 ▸); Koelink et al. (2010 ▸). For general biological activities of thia­zolidinone scaffold compounds, see: Tripathi et al. (2014 ▸).

Experimental

Crystal data

C11H10N2O4S

M = 266.27

Monoclinic,

a = 4.7787 (1) Å

b = 25.4128 (7) Å

c = 18.9599 (5) Å

β = 90.841 (1)°

V = 2302.24 (10) Å3

Z = 8

Cu Kα radiation

μ = 2.62 mm−1

T = 150 K

0.16 × 0.12 × 0.09 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.76, T max = 0.80

17982 measured reflections

4582 independent reflections

3972 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.04

4582 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006416/hg5436sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006416/hg5436Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006416/hg5436Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006416/hg5436fig1.tif

The asymmetric unit for the title compound with labeling scheme and 50% probability ellipsoids. The intra­molecular hydrogen bonds are shown as dotted lines.

Click here for additional data file.

a . DOI: 10.1107/S2056989015006416/hg5436fig2.tif

Packing viewed down the a axis with O—H⋯O (red) N—H⋯O (blue), N—H⋯N (blue), C—H⋯O (black) and C—H⋯S (yellow) inter­actions shown as dotted lines.

Click here for additional data file.

c . DOI: 10.1107/S2056989015006416/hg5436fig3.tif

Packing viewed down the c axis. Key to dotted lines as for Fig. 2.

CCDC reference: 1056711

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H10N2O4S	F(000) = 1104
Mr = 266.27	Dx = 1.536 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 4.7787 (1) Å	Cell parameters from 9975 reflections
b = 25.4128 (7) Å	θ = 4.2–74.5°
c = 18.9599 (5) Å	µ = 2.62 mm−1
β = 90.841 (1)°	T = 150 K
V = 2302.24 (10) Å3	Block, yellow-orange
Z = 8	0.16 × 0.12 × 0.09 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4582 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3972 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4167 pixels mm-1	θmax = 74.5°, θmin = 2.9°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −31→31
Tmin = 0.76, Tmax = 0.80	l = −21→23
17982 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: mixed
wR(F2) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0435P)2 + 1.0566P] where P = (Fo2 + 2Fc2)/3
4582 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. H-atoms attached to carbonwere placed in calculated positions (C—H = 0.95 - 0.98 Å) while thoseattached to nitrogen and oxygen were placed in locations derived from adifference map, refined initially to verify their presence and then theirparameters adjusted to give N—H = 0.91 Å and O—H = 0.84 Å. Allwere included as riding contributions with isotropic displacementparameters 1.2 - 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
S1	0.20576 (11)	0.60092 (2)	0.64250 (2)	0.03308 (12)
O1	0.8378 (3)	0.39435 (5)	0.78252 (7)	0.0340 (3)
H1A	0.7774	0.4013	0.8228	0.041*
O2	0.5442 (3)	0.43997 (5)	0.88146 (6)	0.0313 (3)
O3	0.1993 (3)	0.49520 (5)	0.84894 (6)	0.0296 (3)
O4	−0.2571 (3)	0.64326 (5)	0.48484 (7)	0.0460 (4)
N1	0.1989 (3)	0.50385 (5)	0.58425 (7)	0.0244 (3)
H1N	0.1522	0.4827	0.5471	0.029*
N2	−0.0532 (3)	0.56801 (5)	0.52659 (7)	0.0263 (3)
C1	0.3659 (4)	0.48031 (6)	0.63838 (8)	0.0234 (3)
C2	0.3104 (3)	0.48582 (6)	0.70909 (8)	0.0235 (3)
H2	0.1641	0.5085	0.7237	0.028*
C3	0.4698 (3)	0.45798 (6)	0.75962 (8)	0.0224 (3)
C4	0.6808 (4)	0.42367 (6)	0.73737 (9)	0.0253 (3)
C5	0.7330 (4)	0.41851 (7)	0.66549 (9)	0.0295 (4)
H5	0.8772	0.3957	0.6501	0.035*
C6	0.5769 (4)	0.44630 (7)	0.61680 (9)	0.0264 (3)
H6	0.6131	0.4423	0.5680	0.032*
C7	0.4110 (4)	0.46286 (6)	0.83537 (9)	0.0244 (3)
C8	0.1382 (4)	0.50350 (7)	0.92288 (9)	0.0341 (4)
H8A	0.1074	0.4695	0.9458	0.051*
H8B	−0.0304	0.5252	0.9269	0.051*
H8C	0.2964	0.5215	0.9459	0.051*
C9	0.1095 (4)	0.55291 (6)	0.58058 (8)	0.0235 (3)
C10	−0.1141 (4)	0.62053 (7)	0.52919 (9)	0.0303 (4)
C11	0.0118 (4)	0.64938 (7)	0.59232 (10)	0.0337 (4)
H11A	−0.1376	0.6650	0.6213	0.040*
H11B	0.1374	0.6779	0.5765	0.040*
S2	0.79895 (10)	0.68556 (2)	0.30469 (2)	0.03288 (12)
O5	−0.1163 (3)	0.86366 (5)	0.57459 (6)	0.0311 (3)
H5A	−0.2396	0.8788	0.5500	0.037*
O6	−0.3730 (3)	0.89682 (5)	0.45724 (7)	0.0315 (3)
O7	−0.2248 (3)	0.86409 (5)	0.35416 (6)	0.0359 (3)
O8	0.4930 (3)	0.78782 (5)	0.17658 (7)	0.0369 (3)
N3	0.4978 (3)	0.72813 (5)	0.40544 (7)	0.0266 (3)
H3N	0.5957	0.7034	0.4303	0.032*
N4	0.4467 (3)	0.76550 (5)	0.29297 (7)	0.0273 (3)
C12	0.3322 (3)	0.76357 (6)	0.44516 (9)	0.0244 (3)
C13	0.1336 (3)	0.79618 (6)	0.41508 (9)	0.0242 (3)
H13	0.1002	0.7952	0.3656	0.029*
C14	−0.0191 (3)	0.83065 (6)	0.45723 (8)	0.0232 (3)
C15	0.0258 (3)	0.83183 (6)	0.53042 (9)	0.0249 (3)
C16	0.2281 (4)	0.79875 (7)	0.55986 (9)	0.0284 (4)
H16	0.2617	0.7993	0.6094	0.034*
C17	0.3800 (4)	0.76519 (7)	0.51822 (9)	0.0276 (4)
H17	0.5181	0.7430	0.5391	0.033*
C18	−0.2245 (4)	0.86683 (6)	0.42429 (9)	0.0261 (3)
C19	−0.4239 (5)	0.89664 (8)	0.31670 (11)	0.0464 (5)
H19A	−0.6106	0.8913	0.3361	0.070*
H19B	−0.4260	0.8871	0.2666	0.070*
H19C	−0.3704	0.9337	0.3219	0.070*
C20	0.5553 (3)	0.73108 (6)	0.33708 (9)	0.0250 (3)
C21	0.5600 (4)	0.76067 (7)	0.22716 (9)	0.0283 (4)
C22	0.7842 (4)	0.71821 (7)	0.22087 (9)	0.0330 (4)
H22A	0.9675	0.7342	0.2100	0.040*
H22B	0.7338	0.6930	0.1829	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.0490 (3)	0.0229 (2)	0.0269 (2)	0.00344 (17)	−0.01520 (19)	−0.00436 (15)
O1	0.0388 (7)	0.0389 (7)	0.0241 (6)	0.0151 (5)	−0.0018 (5)	0.0060 (5)
O2	0.0332 (7)	0.0394 (7)	0.0213 (6)	0.0014 (5)	−0.0020 (5)	0.0078 (5)
O3	0.0397 (7)	0.0296 (6)	0.0195 (6)	0.0054 (5)	0.0023 (5)	−0.0006 (5)
O4	0.0700 (10)	0.0286 (7)	0.0385 (8)	0.0144 (6)	−0.0250 (7)	0.0000 (6)
N1	0.0338 (8)	0.0220 (6)	0.0172 (6)	0.0042 (5)	−0.0053 (5)	−0.0024 (5)
N2	0.0373 (8)	0.0222 (6)	0.0193 (7)	0.0057 (6)	−0.0067 (6)	−0.0019 (5)
C1	0.0280 (9)	0.0206 (7)	0.0213 (8)	0.0010 (6)	−0.0042 (6)	0.0018 (6)
C2	0.0275 (9)	0.0209 (7)	0.0220 (8)	0.0015 (6)	−0.0007 (6)	−0.0007 (6)
C3	0.0254 (8)	0.0219 (7)	0.0200 (8)	−0.0018 (6)	−0.0013 (6)	0.0014 (6)
C4	0.0271 (9)	0.0251 (8)	0.0236 (8)	0.0019 (6)	−0.0029 (6)	0.0040 (6)
C5	0.0310 (9)	0.0315 (9)	0.0262 (9)	0.0087 (7)	0.0010 (7)	0.0005 (7)
C6	0.0317 (9)	0.0291 (8)	0.0185 (8)	0.0032 (7)	0.0010 (6)	−0.0006 (6)
C7	0.0271 (9)	0.0231 (7)	0.0231 (8)	−0.0051 (6)	−0.0005 (6)	0.0013 (6)
C8	0.0461 (11)	0.0347 (9)	0.0216 (9)	0.0007 (8)	0.0059 (8)	−0.0030 (7)
C9	0.0301 (9)	0.0228 (7)	0.0175 (7)	0.0012 (6)	−0.0018 (6)	−0.0013 (6)
C10	0.0413 (10)	0.0240 (8)	0.0253 (9)	0.0047 (7)	−0.0066 (7)	−0.0003 (7)
C11	0.0498 (12)	0.0216 (8)	0.0293 (9)	0.0050 (7)	−0.0116 (8)	−0.0010 (7)
S2	0.0378 (3)	0.0296 (2)	0.0314 (2)	0.01298 (17)	0.00235 (18)	0.00021 (17)
O5	0.0353 (7)	0.0344 (6)	0.0237 (6)	0.0065 (5)	0.0015 (5)	−0.0028 (5)
O6	0.0347 (7)	0.0282 (6)	0.0317 (7)	0.0084 (5)	0.0001 (5)	−0.0025 (5)
O7	0.0455 (8)	0.0370 (7)	0.0250 (6)	0.0180 (6)	−0.0089 (5)	−0.0021 (5)
O8	0.0466 (8)	0.0390 (7)	0.0250 (6)	0.0061 (6)	−0.0015 (5)	0.0053 (5)
N3	0.0309 (8)	0.0236 (7)	0.0253 (7)	0.0076 (6)	−0.0014 (6)	0.0039 (5)
N4	0.0316 (8)	0.0259 (7)	0.0242 (7)	0.0052 (6)	−0.0002 (6)	0.0011 (5)
C12	0.0265 (9)	0.0217 (7)	0.0250 (8)	0.0011 (6)	0.0018 (6)	0.0017 (6)
C13	0.0264 (9)	0.0244 (8)	0.0218 (8)	0.0001 (6)	−0.0022 (6)	0.0003 (6)
C14	0.0242 (8)	0.0220 (7)	0.0233 (8)	−0.0011 (6)	−0.0016 (6)	0.0008 (6)
C15	0.0262 (9)	0.0244 (8)	0.0241 (8)	−0.0024 (6)	0.0017 (6)	−0.0001 (6)
C16	0.0316 (9)	0.0330 (9)	0.0206 (8)	−0.0009 (7)	−0.0015 (7)	0.0027 (6)
C17	0.0280 (9)	0.0289 (8)	0.0257 (9)	0.0023 (7)	−0.0016 (7)	0.0070 (7)
C18	0.0288 (9)	0.0230 (8)	0.0265 (9)	0.0004 (6)	−0.0028 (7)	−0.0017 (6)
C19	0.0601 (14)	0.0448 (12)	0.0338 (11)	0.0248 (10)	−0.0156 (9)	0.0000 (8)
C20	0.0255 (8)	0.0212 (7)	0.0282 (9)	0.0025 (6)	−0.0003 (6)	−0.0017 (6)
C21	0.0317 (9)	0.0272 (8)	0.0260 (9)	−0.0015 (7)	−0.0026 (7)	−0.0026 (7)
C22	0.0344 (10)	0.0375 (10)	0.0272 (9)	0.0069 (8)	0.0002 (7)	−0.0032 (7)

S1—C9	1.7500 (16)	S2—C20	1.7585 (16)
S1—C11	1.8043 (17)	S2—C22	1.7933 (19)
O1—C4	1.353 (2)	O5—C15	1.354 (2)
O1—H1A	0.8400	O5—H5A	0.8400
O2—C7	1.221 (2)	O6—C18	1.220 (2)
O3—C7	1.331 (2)	O7—C18	1.331 (2)
O3—C8	1.452 (2)	O7—C19	1.440 (2)
O4—C10	1.221 (2)	O8—C21	1.220 (2)
N1—C9	1.319 (2)	N3—C20	1.331 (2)
N1—C1	1.422 (2)	N3—C12	1.422 (2)
N1—H1N	0.9099	N3—H3N	0.9098
N2—C9	1.333 (2)	N4—C20	1.312 (2)
N2—C10	1.367 (2)	N4—C21	1.373 (2)
C1—C2	1.378 (2)	C12—C13	1.377 (2)
C1—C6	1.394 (2)	C12—C17	1.401 (2)
C2—C3	1.406 (2)	C13—C14	1.398 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.403 (2)	C14—C15	1.401 (2)
C3—C7	1.473 (2)	C14—C18	1.477 (2)
C4—C5	1.395 (2)	C15—C16	1.392 (2)
C5—C6	1.374 (2)	C16—C17	1.377 (2)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—H8A	0.9800	C19—H19A	0.9800
C8—H8B	0.9800	C19—H19B	0.9800
C8—H8C	0.9800	C19—H19C	0.9800
C10—C11	1.520 (2)	C21—C22	1.526 (2)
C11—H11A	0.9900	C22—H22A	0.9900
C11—H11B	0.9900	C22—H22B	0.9900
C9—S1—C11	89.67 (8)	C20—S2—C22	89.28 (8)
C4—O1—H1A	105.4	C15—O5—H5A	106.6
C7—O3—C8	116.14 (13)	C18—O7—C19	116.99 (14)
C9—N1—C1	127.82 (14)	C20—N3—C12	127.20 (14)
C9—N1—H1N	116.1	C20—N3—H3N	115.5
C1—N1—H1N	116.0	C12—N3—H3N	116.7
C9—N2—C10	112.07 (14)	C20—N4—C21	111.24 (14)
C2—C1—C6	119.94 (15)	C13—C12—C17	119.54 (15)
C2—C1—N1	123.06 (15)	C13—C12—N3	123.18 (15)
C6—C1—N1	116.70 (14)	C17—C12—N3	117.27 (14)
C1—C2—C3	120.12 (15)	C12—C13—C14	120.16 (15)
C1—C2—H2	119.9	C12—C13—H13	119.9
C3—C2—H2	119.9	C14—C13—H13	119.9
C4—C3—C2	119.52 (15)	C13—C14—C15	120.37 (15)
C4—C3—C7	119.59 (14)	C13—C14—C18	119.84 (15)
C2—C3—C7	120.85 (15)	C15—C14—C18	119.78 (15)
O1—C4—C5	117.43 (15)	O5—C15—C16	117.68 (15)
O1—C4—C3	123.12 (15)	O5—C15—C14	123.66 (15)
C5—C4—C3	119.44 (15)	C16—C15—C14	118.66 (15)
C6—C5—C4	120.33 (16)	C17—C16—C15	120.89 (16)
C6—C5—H5	119.8	C17—C16—H16	119.6
C4—C5—H5	119.8	C15—C16—H16	119.6
C5—C6—C1	120.63 (15)	C16—C17—C12	120.36 (16)
C5—C6—H6	119.7	C16—C17—H17	119.8
C1—C6—H6	119.7	C12—C17—H17	119.8
O2—C7—O3	123.05 (15)	O6—C18—O7	123.49 (15)
O2—C7—C3	123.57 (16)	O6—C18—C14	124.10 (15)
O3—C7—C3	113.38 (14)	O7—C18—C14	112.39 (14)
O3—C8—H8A	109.5	O7—C19—H19A	109.5
O3—C8—H8B	109.5	O7—C19—H19B	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
O3—C8—H8C	109.5	O7—C19—H19C	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
N1—C9—N2	119.84 (14)	N4—C20—N3	124.96 (15)
N1—C9—S1	122.80 (12)	N4—C20—S2	118.27 (13)
N2—C9—S1	117.33 (12)	N3—C20—S2	116.77 (12)
O4—C10—N2	123.68 (16)	O8—C21—N4	124.13 (17)
O4—C10—C11	121.66 (15)	O8—C21—C22	120.97 (16)
N2—C10—C11	114.66 (14)	N4—C21—C22	114.89 (15)
C10—C11—S1	106.27 (11)	C21—C22—S2	106.04 (12)
C10—C11—H11A	110.5	C21—C22—H22A	110.5
S1—C11—H11A	110.5	S2—C22—H22A	110.5
C10—C11—H11B	110.5	C21—C22—H22B	110.5
S1—C11—H11B	110.5	S2—C22—H22B	110.5
H11A—C11—H11B	108.7	H22A—C22—H22B	108.7
C9—N1—C1—C2	47.7 (3)	C20—N3—C12—C13	22.3 (3)
C9—N1—C1—C6	−138.67 (18)	C20—N3—C12—C17	−156.84 (17)
C6—C1—C2—C3	1.2 (2)	C17—C12—C13—C14	0.0 (2)
N1—C1—C2—C3	174.71 (15)	N3—C12—C13—C14	−179.07 (15)
C1—C2—C3—C4	−1.5 (2)	C12—C13—C14—C15	−0.9 (2)
C1—C2—C3—C7	−179.19 (15)	C12—C13—C14—C18	177.82 (15)
C2—C3—C4—O1	−178.04 (15)	C13—C14—C15—O5	−179.17 (15)
C7—C3—C4—O1	−0.3 (2)	C18—C14—C15—O5	2.1 (2)
C2—C3—C4—C5	1.3 (2)	C13—C14—C15—C16	1.1 (2)
C7—C3—C4—C5	178.98 (15)	C18—C14—C15—C16	−177.59 (15)
O1—C4—C5—C6	178.58 (16)	O5—C15—C16—C17	179.77 (15)
C3—C4—C5—C6	−0.8 (3)	C14—C15—C16—C17	−0.5 (3)
C4—C5—C6—C1	0.5 (3)	C15—C16—C17—C12	−0.4 (3)
C2—C1—C6—C5	−0.7 (3)	C13—C12—C17—C16	0.6 (3)
N1—C1—C6—C5	−174.61 (16)	N3—C12—C17—C16	179.74 (15)
C8—O3—C7—O2	1.9 (2)	C19—O7—C18—O6	−3.5 (3)
C8—O3—C7—C3	−177.46 (14)	C19—O7—C18—C14	178.15 (16)
C4—C3—C7—O2	3.0 (2)	C13—C14—C18—O6	177.39 (16)
C2—C3—C7—O2	−179.34 (16)	C15—C14—C18—O6	−3.9 (3)
C4—C3—C7—O3	−177.66 (14)	C13—C14—C18—O7	−4.2 (2)
C2—C3—C7—O3	0.0 (2)	C15—C14—C18—O7	174.46 (15)
C1—N1—C9—N2	−178.03 (16)	C21—N4—C20—N3	176.22 (16)
C1—N1—C9—S1	4.4 (3)	C21—N4—C20—S2	−3.0 (2)
C10—N2—C9—N1	−176.80 (16)	C12—N3—C20—N4	−6.2 (3)
C10—N2—C9—S1	0.9 (2)	C12—N3—C20—S2	172.97 (13)
C11—S1—C9—N1	176.98 (16)	C22—S2—C20—N4	4.75 (15)
C11—S1—C9—N2	−0.60 (15)	C22—S2—C20—N3	−174.50 (14)
C9—N2—C10—O4	179.11 (19)	C20—N4—C21—O8	179.46 (17)
C9—N2—C10—C11	−0.7 (2)	C20—N4—C21—C22	−1.1 (2)
O4—C10—C11—S1	−179.56 (17)	O8—C21—C22—S2	−176.26 (15)
N2—C10—C11—S1	0.3 (2)	N4—C21—C22—S2	4.23 (19)
C9—S1—C11—C10	0.17 (14)	C20—S2—C22—C21	−4.54 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.84	1.87	2.6287 (18)	150
O5—H5A···O6	0.84	1.92	2.6619 (18)	147
N1—H1N···N2i	0.91	1.96	2.8624 (19)	175
N3—H3N···O4ii	0.91	1.97	2.8703 (18)	170
C11—H11A···O8iii	0.99	2.39	3.371 (2)	171
C5—H5···S2iv	0.95	2.71	3.5043 (18)	141

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1AO2	0.84	1.87	2.6287(18)	150
O5H5AO6	0.84	1.92	2.6619(18)	147
N1H1NN2i	0.91	1.96	2.8624(19)	175
N3H3NO4ii	0.91	1.97	2.8703(18)	170
C11H11AO8iii	0.99	2.39	3.371(2)	171
C5H5S2iv	0.95	2.71	3.5043(18)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .