5H-Thio-chromeno[2,3-b]pyridine-5,10,10-trione.

The asymmetric unit of the title compound, C(12)H(7)NO(3)S, contains two independent mol-ecules with different geometric-al configurations. The dihedral angles between the benzene and pyridine rings in the two mol-ecules are 3.7 (2) and 5.40 (19)°. The central heterocyclic fused rings have different puckering parameters [Q = 0.122 (3) Å, θ = 100.4 (13), ϕ = 185.3 (19)° in one mol-ecule, 0.101 (3) Å, 101.4 (3) and 2 (2)° in the other]. The SO(2) group is oriented at dihedral angles of 81.06 (14) and 82.58 (15)° with the benzene and pyridine rings, respectively, in one mol-ecule [87.21 (14) and 87.66 (14)° in the second]. In the crystal, the mol-ecules are linked into zigzag polymeric chains along the b axis by inter-molecular C-H⋯O hydrogen bonding. π-π inter-actions with centroid-centroid distances in the range 3.825 (3)-4.153 (3) Å stabilize the structure. S-O⋯π and C-O⋯π inter-actions are also observed.

Related literature

For background to our work on pyridine- and thio-containing heterocyclic rings and for related structures, see: Khan et al. (2008 ▶). For the preparation, see: Khan et al. (2008 ▶); Kruger & Mann (1954 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H7NO3S

M = 245.25

Orthorhombic,

a = 12.157 (5) Å

b = 11.483 (5) Å

c = 14.964 (7) Å

V = 2089.0 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.35 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.985

29502 measured reflections

3718 independent reflections

2838 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.094

S = 1.04

3718 reflections

307 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1749 Friedel pairs

Flack parameter: 0.13 (9)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038171/bq2235sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038171/bq2235Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H7NO3S	F(000) = 1008
Mr = 245.25	Dx = 1.560 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2838 reflections
a = 12.157 (5) Å	θ = 2.2–25.2°
b = 11.483 (5) Å	µ = 0.30 mm−1
c = 14.964 (7) Å	T = 296 K
V = 2089.0 (16) Å3	Needle, white
Z = 8	0.35 × 0.14 × 0.12 mm

Bruker Kappa APEXII CCD diffractometer	3718 independent reflections
Radiation source: fine-focus sealed tube	2838 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 8.10 pixels mm-1	θmax = 25.2°, θmin = 2.4°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.968, Tmax = 0.985	l = −17→17
29502 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.043P)2 + 0.3395P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3718 reflections	Δρmax = 0.20 e Å−3
307 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1749 Friedal pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (9)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.81953 (6)	0.23202 (7)	0.11098 (7)	0.0396 (3)
O1	0.4807 (2)	0.2221 (2)	0.2163 (2)	0.0604 (10)
O2	0.8585 (2)	0.2231 (2)	0.0215 (2)	0.0605 (10)
O3	0.90038 (19)	0.2461 (2)	0.1799 (2)	0.0515 (10)
N1	0.7975 (3)	0.0089 (3)	0.1253 (4)	0.0579 (16)
C1	0.7263 (2)	0.3484 (3)	0.1177 (2)	0.0396 (11)
C2	0.7670 (3)	0.4540 (3)	0.0899 (3)	0.0480 (14)
C3	0.7021 (3)	0.5509 (4)	0.0970 (3)	0.0620 (17)
C4	0.5960 (3)	0.5429 (4)	0.1313 (3)	0.0603 (18)
C5	0.5556 (3)	0.4373 (4)	0.1565 (3)	0.0517 (16)
C6	0.6192 (3)	0.3367 (3)	0.1509 (2)	0.0394 (11)
C7	0.5707 (3)	0.2240 (3)	0.1802 (2)	0.0410 (12)
C8	0.6319 (3)	0.1143 (3)	0.1664 (3)	0.0407 (11)
C9	0.5807 (3)	0.0072 (3)	0.1860 (4)	0.0523 (18)
C10	0.6387 (4)	−0.0949 (3)	0.1760 (3)	0.0590 (19)
C11	0.7462 (4)	−0.0915 (4)	0.1467 (3)	0.0620 (18)
C12	0.7393 (3)	0.1068 (3)	0.1364 (3)	0.0389 (14)
S2	0.55676 (6)	0.72967 (8)	0.42422 (7)	0.0439 (3)
O4	0.2126 (2)	0.7236 (2)	0.33032 (18)	0.0491 (9)
O5	0.5968 (2)	0.7223 (2)	0.5146 (2)	0.0701 (11)
O6	0.6358 (2)	0.7403 (2)	0.3539 (2)	0.0635 (10)
N2	0.5313 (3)	0.5063 (3)	0.4106 (3)	0.0539 (13)
C13	0.4655 (2)	0.8471 (3)	0.4173 (3)	0.0391 (11)
C14	0.5086 (3)	0.9534 (3)	0.4424 (3)	0.0550 (16)
C15	0.4448 (3)	1.0509 (4)	0.4341 (4)	0.0687 (19)
C16	0.3396 (3)	1.0443 (4)	0.4026 (4)	0.0660 (19)
C17	0.2959 (3)	0.9386 (3)	0.3784 (3)	0.0533 (16)
C18	0.3576 (3)	0.8374 (3)	0.3856 (2)	0.0392 (11)
C19	0.3053 (3)	0.7249 (3)	0.3592 (2)	0.0392 (11)
C20	0.3670 (3)	0.6127 (3)	0.3704 (3)	0.0365 (11)
C21	0.3156 (3)	0.5088 (3)	0.3504 (4)	0.0473 (16)
C22	0.3716 (3)	0.4060 (3)	0.3600 (3)	0.0540 (16)
C23	0.4783 (4)	0.4074 (4)	0.3899 (3)	0.0567 (19)
C24	0.4750 (3)	0.6059 (3)	0.4004 (3)	0.0384 (11)
H2	0.83773	0.45951	0.06657	0.0578*
H3	0.72920	0.62284	0.07869	0.0744*
H4	0.55289	0.60938	0.13709	0.0725*
H5	0.48391	0.43225	0.17780	0.0621*
H9	0.50812	0.00552	0.20555	0.0627*
H10	0.60550	−0.16592	0.18901	0.0705*
H11	0.78485	−0.16105	0.14140	0.0741*
H14	0.57990	0.95872	0.46456	0.0658*
H15	0.47355	1.12296	0.45013	0.0823*
H16	0.29745	1.11160	0.39751	0.0790*
H17	0.22412	0.93488	0.35701	0.0641*
H21	0.24310	0.50852	0.33052	0.0567*
H22	0.33746	0.33569	0.34637	0.0648*
H23	0.51535	0.33705	0.39606	0.0682*

	U11	U22	U33	U12	U13	U23
S1	0.0312 (4)	0.0449 (5)	0.0428 (5)	−0.0024 (4)	0.0075 (4)	0.0005 (6)
O1	0.0356 (14)	0.0615 (19)	0.084 (2)	−0.0044 (13)	0.0160 (15)	0.0022 (16)
O2	0.0675 (17)	0.063 (2)	0.0510 (16)	−0.0010 (15)	0.0260 (15)	0.0026 (15)
O3	0.0278 (12)	0.0550 (18)	0.0716 (19)	−0.0022 (12)	−0.0036 (12)	0.0009 (14)
N1	0.0506 (19)	0.046 (2)	0.077 (4)	−0.0001 (16)	0.001 (2)	−0.0009 (19)
C1	0.0339 (18)	0.048 (2)	0.037 (2)	−0.0020 (15)	−0.0044 (17)	0.0073 (19)
C2	0.041 (2)	0.044 (2)	0.059 (3)	−0.0074 (18)	0.012 (2)	0.008 (2)
C3	0.066 (3)	0.047 (3)	0.073 (3)	−0.004 (2)	−0.002 (3)	0.013 (2)
C4	0.056 (2)	0.046 (3)	0.079 (4)	0.013 (2)	0.001 (2)	0.007 (2)
C5	0.039 (2)	0.054 (3)	0.062 (3)	0.007 (2)	0.002 (2)	0.004 (2)
C6	0.0312 (18)	0.048 (2)	0.039 (2)	0.0023 (16)	−0.0043 (15)	0.0007 (16)
C7	0.031 (2)	0.049 (2)	0.043 (2)	−0.0046 (17)	−0.0005 (16)	0.0049 (18)
C8	0.0320 (19)	0.047 (2)	0.043 (2)	−0.0072 (18)	−0.0023 (17)	0.0030 (19)
C9	0.041 (2)	0.060 (3)	0.056 (4)	−0.011 (2)	−0.002 (2)	0.007 (2)
C10	0.058 (3)	0.042 (3)	0.077 (4)	−0.012 (2)	−0.006 (2)	0.006 (2)
C11	0.059 (2)	0.043 (3)	0.084 (4)	−0.002 (2)	0.002 (3)	−0.004 (2)
C12	0.0348 (19)	0.041 (2)	0.041 (3)	0.0000 (17)	−0.0007 (17)	0.0009 (18)
S2	0.0301 (4)	0.0465 (5)	0.0551 (6)	−0.0046 (4)	−0.0106 (4)	0.0082 (7)
O4	0.0295 (14)	0.0615 (17)	0.0564 (18)	0.0004 (12)	−0.0134 (13)	−0.0057 (14)
O5	0.0752 (19)	0.065 (2)	0.070 (2)	−0.0092 (15)	−0.0416 (18)	0.0119 (16)
O6	0.0373 (15)	0.0631 (19)	0.090 (2)	−0.0025 (13)	0.0133 (15)	0.0150 (15)
N2	0.0447 (17)	0.049 (2)	0.068 (3)	0.0048 (15)	−0.007 (2)	0.0099 (17)
C13	0.0334 (18)	0.043 (2)	0.041 (2)	−0.0044 (15)	−0.0053 (17)	0.0032 (18)
C14	0.041 (2)	0.052 (3)	0.072 (3)	−0.009 (2)	−0.011 (2)	0.003 (2)
C15	0.070 (3)	0.044 (3)	0.092 (4)	−0.009 (2)	−0.012 (3)	−0.004 (3)
C16	0.062 (3)	0.048 (3)	0.088 (4)	0.012 (2)	−0.004 (3)	−0.005 (3)
C17	0.042 (2)	0.053 (3)	0.065 (3)	0.0102 (19)	−0.007 (2)	−0.010 (2)
C18	0.0316 (18)	0.047 (2)	0.039 (2)	0.0004 (16)	−0.0020 (15)	−0.0030 (15)
C19	0.034 (2)	0.052 (2)	0.0317 (19)	−0.0013 (17)	0.0002 (16)	0.0005 (17)
C20	0.0294 (18)	0.044 (2)	0.036 (2)	−0.0040 (17)	0.0018 (15)	0.0006 (17)
C21	0.039 (2)	0.049 (3)	0.054 (3)	−0.0090 (19)	0.002 (2)	−0.004 (2)
C22	0.051 (2)	0.044 (3)	0.067 (3)	−0.012 (2)	0.009 (2)	−0.004 (2)
C23	0.058 (3)	0.037 (3)	0.075 (4)	0.008 (2)	0.006 (2)	0.003 (2)
C24	0.0362 (19)	0.039 (2)	0.040 (2)	0.0010 (17)	0.0031 (17)	0.0052 (18)

S1—O2	1.424 (3)	C2—H2	0.9300
S1—O3	1.434 (3)	C3—H3	0.9300
S1—C1	1.755 (3)	C4—H4	0.9300
S1—C12	1.779 (4)	C5—H5	0.9300
S2—O5	1.440 (3)	C9—H9	0.9300
S2—O6	1.430 (3)	C10—H10	0.9300
S2—C13	1.749 (3)	C11—H11	0.9300
S2—C24	1.771 (4)	C13—C14	1.380 (5)
O1—C7	1.220 (4)	C13—C18	1.399 (5)
O4—C19	1.207 (4)	C14—C15	1.368 (6)
N1—C11	1.349 (6)	C15—C16	1.365 (6)
N1—C12	1.339 (5)	C16—C17	1.374 (6)
N2—C23	1.342 (6)	C17—C18	1.387 (5)
N2—C24	1.342 (5)	C18—C19	1.493 (5)
C1—C2	1.374 (5)	C19—C20	1.500 (5)
C1—C6	1.400 (4)	C20—C21	1.380 (5)
C2—C3	1.368 (6)	C20—C24	1.390 (5)
C3—C4	1.391 (5)	C21—C22	1.370 (5)
C4—C5	1.362 (6)	C22—C23	1.372 (6)
C5—C6	1.393 (6)	C14—H14	0.9300
C6—C7	1.488 (5)	C15—H15	0.9300
C7—C8	1.478 (5)	C16—H16	0.9300
C8—C12	1.383 (5)	C17—H17	0.9300
C8—C9	1.409 (5)	C21—H21	0.9300
C9—C10	1.376 (5)	C22—H22	0.9300
C10—C11	1.379 (7)	C23—H23	0.9300
O1···C22	3.293 (5)	N2···O6	3.091 (5)
O1···C23	3.358 (6)	N2···O5	3.035 (5)
O1···O5i	3.226 (4)	N1···H14iii	2.8900
O1···C11ii	3.385 (6)	N1···H9iv	2.8300
O2···C17i	3.400 (5)	N2···H2viii	2.8800
O2···N1	3.002 (5)	N2···H21v	2.8500
O2···O4i	3.051 (4)	C1···O4v	3.292 (4)
O2···C15iii	3.367 (5)	C3···O5x	3.372 (5)
O2···C18i	3.394 (5)	C5···O5i	3.362 (5)
O2···C19i	3.197 (5)	C6···O4v	2.996 (4)
O3···N1	3.107 (5)	C6···O5i	3.393 (5)
O3···C10iv	3.378 (5)	C7···O4v	2.896 (4)
O3···C19v	2.940 (4)	C7···O5i	3.266 (5)
O3···O4v	3.225 (4)	C8···O4v	3.232 (5)
O3···C20v	3.305 (5)	C10···O6xiii	3.266 (5)
O3···C18v	3.266 (4)	C10···O3ii	3.378 (5)
O4···O3vi	3.225 (4)	C11···O1iv	3.385 (6)
O4···O2vii	3.051 (4)	C15···O2xi	3.367 (5)
O4···C23vi	3.342 (6)	C17···O2vii	3.400 (5)
O4···C6vi	2.996 (4)	C18···O3vi	3.266 (4)
O4···C1vi	3.292 (4)	C18···O2vii	3.394 (5)
O4···C8vi	3.232 (5)	C19···O2vii	3.197 (5)
O4···C7vi	2.896 (4)	C19···O3vi	2.940 (4)
O5···C5vii	3.362 (5)	C20···O3vi	3.305 (5)
O5···N2	3.035 (5)	C22···O1	3.293 (5)
O5···C3viii	3.372 (5)	C22···O6vi	3.324 (5)
O5···C7vii	3.266 (5)	C23···O1	3.358 (6)
O5···O1vii	3.226 (4)	C23···O4v	3.342 (6)
O5···C6vii	3.393 (5)	C22···H5	3.0600
O6···C22v	3.324 (5)	H2···O2	2.8100
O6···C10ix	3.266 (5)	H2···N2x	2.8800
O6···N2	3.091 (5)	H3···O5x	2.5900
O1···H9	2.5100	H4···O3vi	2.5700
O1···H11ii	2.7200	H5···C22	3.0600
O1···H5	2.4800	H5···O1	2.4800
O1···H22	2.9200	H9···O1	2.5100
O2···H2	2.8100	H9···N1ii	2.8300
O2···H23x	2.7500	H10···O6xiii	2.7200
O2···H15iii	2.5800	H10···O3ii	2.6600
O3···H4v	2.5700	H11···O5iii	2.7300
O3···H10iv	2.6600	H11···O1iv	2.7200
O4···H21	2.5000	H14···O5	2.8200
O4···H17	2.4600	H14···N1xi	2.8900
O4···H23vi	2.6800	H15···O2xi	2.5800
O5···H11xi	2.7300	H16···O6xiv	2.6800
O5···H14	2.8200	H17···O4	2.4600
O5···H3viii	2.5900	H21···O4	2.5000
O6···H16xii	2.6800	H21···N2vi	2.8500
O6···H10ix	2.7200	H22···O1	2.9200
O6···H22v	2.6000	H22···O6vi	2.6000
N1···O3	3.107 (5)	H23···O2viii	2.7500
N1···O2	3.002 (5)	H23···O4v	2.6800
O2—S1—O3	117.15 (15)	C6—C5—H5	119.00
O2—S1—C1	108.87 (15)	C8—C9—H9	120.00
O2—S1—C12	108.99 (18)	C10—C9—H9	120.00
O3—S1—C1	108.40 (14)	C9—C10—H10	120.00
O3—S1—C12	108.26 (18)	C11—C10—H10	120.00
C1—S1—C12	104.43 (15)	N1—C11—H11	119.00
O5—S2—C13	108.38 (18)	C10—C11—H11	119.00
O5—S2—C24	109.37 (18)	S2—C13—C14	115.1 (2)
O6—S2—C13	108.47 (17)	S2—C13—C18	123.6 (3)
O6—S2—C24	107.31 (18)	C14—C13—C18	121.2 (3)
C13—S2—C24	104.53 (16)	C13—C14—C15	118.9 (3)
O5—S2—O6	117.97 (16)	C14—C15—C16	121.2 (4)
C11—N1—C12	116.4 (4)	C15—C16—C17	120.2 (4)
C23—N2—C24	116.8 (4)	C16—C17—C18	120.7 (4)
S1—C1—C2	115.0 (2)	C13—C18—C17	117.8 (3)
S1—C1—C6	123.2 (3)	C13—C18—C19	123.9 (3)
C2—C1—C6	121.8 (3)	C17—C18—C19	118.3 (3)
C1—C2—C3	119.1 (3)	O4—C19—C18	120.2 (3)
C2—C3—C4	120.6 (4)	O4—C19—C20	119.8 (3)
C3—C4—C5	119.7 (4)	C18—C19—C20	120.0 (3)
C4—C5—C6	121.5 (3)	C19—C20—C21	119.5 (3)
C1—C6—C5	117.3 (3)	C19—C20—C24	123.8 (3)
C5—C6—C7	118.9 (3)	C21—C20—C24	116.7 (3)
C1—C6—C7	123.8 (3)	C20—C21—C22	119.8 (4)
O1—C7—C8	119.9 (3)	C21—C22—C23	119.6 (4)
C6—C7—C8	120.1 (3)	N2—C23—C22	122.6 (4)
O1—C7—C6	120.1 (3)	S2—C24—N2	112.0 (3)
C7—C8—C9	119.5 (3)	S2—C24—C20	123.4 (3)
C7—C8—C12	125.0 (3)	N2—C24—C20	124.5 (3)
C9—C8—C12	115.5 (3)	C13—C14—H14	121.00
C8—C9—C10	119.6 (4)	C15—C14—H14	120.00
C9—C10—C11	119.7 (4)	C14—C15—H15	119.00
N1—C11—C10	122.5 (4)	C16—C15—H15	119.00
S1—C12—N1	111.3 (3)	C15—C16—H16	120.00
S1—C12—C8	122.5 (3)	C17—C16—H16	120.00
N1—C12—C8	126.3 (3)	C16—C17—H17	120.00
C3—C2—H2	120.00	C18—C17—H17	120.00
C1—C2—H2	120.00	C20—C21—H21	120.00
C2—C3—H3	120.00	C22—C21—H21	120.00
C4—C3—H3	120.00	C21—C22—H22	120.00
C5—C4—H4	120.00	C23—C22—H22	120.00
C3—C4—H4	120.00	N2—C23—H23	119.00
C4—C5—H5	119.00	C22—C23—H23	119.00
O2—S1—C1—C2	−56.2 (3)	C1—C6—C7—C8	−6.4 (5)
O2—S1—C1—C6	125.4 (3)	C5—C6—C7—O1	−6.9 (5)
O3—S1—C1—C2	72.3 (3)	C5—C6—C7—C8	173.7 (3)
O3—S1—C1—C6	−106.1 (3)	O1—C7—C8—C9	7.0 (6)
C12—S1—C1—C2	−172.5 (3)	O1—C7—C8—C12	−171.8 (4)
C12—S1—C1—C6	9.1 (3)	C6—C7—C8—C9	−173.6 (4)
O2—S1—C12—N1	57.7 (4)	C6—C7—C8—C12	7.6 (6)
O2—S1—C12—C8	−124.3 (4)	C7—C8—C9—C10	−177.9 (4)
O3—S1—C12—N1	−70.7 (4)	C12—C8—C9—C10	1.0 (7)
O3—S1—C12—C8	107.3 (4)	C7—C8—C12—S1	0.6 (6)
C1—S1—C12—N1	173.9 (4)	C7—C8—C12—N1	178.3 (5)
C1—S1—C12—C8	−8.0 (4)	C9—C8—C12—S1	−178.3 (4)
O5—S2—C13—C18	−125.2 (3)	C9—C8—C12—N1	−0.5 (7)
O6—S2—C13—C14	−72.0 (4)	C8—C9—C10—C11	−0.2 (8)
O6—S2—C13—C18	105.6 (3)	C9—C10—C11—N1	−1.4 (8)
C24—S2—C13—C14	173.7 (3)	S2—C13—C14—C15	176.3 (4)
C24—S2—C13—C18	−8.7 (4)	C18—C13—C14—C15	−1.4 (7)
O5—S2—C24—N2	−58.7 (4)	S2—C13—C18—C17	−176.1 (3)
O5—S2—C24—C20	124.3 (4)	S2—C13—C18—C19	3.9 (5)
O6—S2—C24—N2	70.3 (4)	C14—C13—C18—C17	1.3 (6)
O6—S2—C24—C20	−106.7 (4)	C14—C13—C18—C19	−178.7 (4)
C13—S2—C24—N2	−174.6 (3)	C13—C14—C15—C16	0.8 (8)
C13—S2—C24—C20	8.4 (4)	C14—C15—C16—C17	−0.1 (9)
O5—S2—C13—C14	57.2 (4)	C15—C16—C17—C18	0.0 (8)
C11—N1—C12—C8	−0.9 (8)	C16—C17—C18—C13	−0.6 (6)
C12—N1—C11—C10	1.8 (8)	C16—C17—C18—C19	179.4 (4)
C11—N1—C12—S1	177.1 (4)	C13—C18—C19—O4	−178.2 (3)
C23—N2—C24—S2	−176.8 (3)	C13—C18—C19—C20	3.2 (5)
C23—N2—C24—C20	0.1 (7)	C17—C18—C19—O4	1.8 (5)
C24—N2—C23—C22	−0.3 (7)	C17—C18—C19—C20	−176.8 (3)
S1—C1—C6—C5	177.0 (3)	O4—C19—C20—C21	−2.2 (6)
S1—C1—C2—C3	−176.7 (3)	O4—C19—C20—C24	177.9 (4)
C6—C1—C2—C3	1.7 (6)	C18—C19—C20—C21	176.4 (4)
C2—C1—C6—C7	178.8 (3)	C18—C19—C20—C24	−3.5 (6)
S1—C1—C6—C7	−2.9 (4)	C19—C20—C21—C22	179.7 (4)
C2—C1—C6—C5	−1.3 (5)	C24—C20—C21—C22	−0.4 (7)
C1—C2—C3—C4	−0.4 (7)	C19—C20—C24—S2	−3.3 (6)
C2—C3—C4—C5	−1.2 (7)	C19—C20—C24—N2	−179.9 (4)
C3—C4—C5—C6	1.7 (7)	C21—C20—C24—S2	176.8 (4)
C4—C5—C6—C7	179.5 (4)	C21—C20—C24—N2	0.2 (7)
C4—C5—C6—C1	−0.4 (6)	C20—C21—C22—C23	0.3 (8)
C1—C6—C7—O1	173.0 (3)	C21—C22—C23—N2	0.1 (7)

Cg1 and Cg2 are the centroids of the S1/C1/C6/C7/C8/C12 and S2/C13/C18/C19/C20/C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5x	0.93	2.59	3.372 (5)	142
C4—H4···O3vi	0.93	2.57	3.472 (5)	164
C15—H15···O2xi	0.93	2.58	3.367 (5)	143
S1—O3···Cg2xi	1.434 (3)	3.212 (4)	4.421 (3)	141.14 (14)
C19—O4···Cg1vi	1.207 (4)	2.869 (3)	3.585 (4)	117.2 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/C1/C6/C7/C8/C12 and S2/C13/C18/C19/C20/C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O5i	0.93	2.59	3.372 (5)	142
C4—H4⋯O3ii	0.93	2.57	3.472 (5)	164
C15—H15⋯O2iii	0.93	2.58	3.367 (5)	143
S1—O3⋯Cg2iii	1.43 (1)	3.21 (1)	4.421 (3)	141 (1)
C19—O4⋯Cg1ii	1.21 (1)	2.87 (1)	3.585 (4)	117 (1)

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