N-[5-Methyl-2-(2-nitro-phen-yl)-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide monohydrate.

In the title compound, C(16)H(14)N(4)O(4)S·H(2)O, the benzene and pyridine rings make a dihedral angle of 85.8 (1)°. Both enanti-omers of the chiral title compound are statistically disordered over the same position in the unit cell. The methyl and carbonyl group attached to the stereogenic center (C(5) of the thia-zolidine ring) were therefore refined with common site-occupation factors of 0.531 (9) and 0.469 (9), respectively, for each stereoisomer. In the crystal, inter-molecular N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules, forming a three-dimensional supra-molecular network. The crystal structure further shows π-π stacking inter-actions [centroid-centroid distance = 3.5063 (13) Å] between the pyridine rings.

Related literature

For the biological and pharmacological properties of pyridine-3-carboxamide derivatives, see: Balzarini et al. (2009 ▶); Baumbach et al. (1995 ▶); Girgis et al. (2006 ▶); Guzel & Salman (2009 ▶); Kuramochi et al. (2005 ▶); Moëll et al. (2009 ▶); Slominska et al. (2008 ▶); Ur et al. (2004 ▶); Vigorita et al. (1992 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14N4O4S·H2O

M = 376.40

Triclinic,

a = 8.1399 (4) Å

b = 8.4106 (4) Å

c = 15.0274 (7) Å

α = 92.957 (4)°

β = 104.176 (4)°

γ = 116.792 (4)°

V = 874.66 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.62 × 0.55 × 0.49 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.875, T max = 0.899

11714 measured reflections

3963 independent reflections

3192 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.04

3963 reflections

285 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000481/im2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000481/im2255Isup2.hkl

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

C16H14N4O4S·H2O	Z = 2
Mr = 376.40	F(000) = 392
Triclinic, P1	Dx = 1.429 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1399 (4) Å	Cell parameters from 15771 reflections
b = 8.4106 (4) Å	θ = 2.8–28.0°
c = 15.0274 (7) Å	µ = 0.22 mm−1
α = 92.957 (4)°	T = 296 K
β = 104.176 (4)°	Block, colourless
γ = 116.792 (4)°	0.62 × 0.55 × 0.49 mm
V = 874.66 (8) Å3

Stoe IPDS 2 diffractometer	3963 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3192 reflections with I > 2σ(I)
plane graphite	Rint = 0.038
Detector resolution: 6.67 pixels mm-1	θmax = 27.5°, θmin = 2.8°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.875, Tmax = 0.899	l = −19→18
11714 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.057P)2 + 0.1358P] where P = (Fo2 + 2Fc2)/3
3963 reflections	(Δ/σ)max = 0.001
285 parameters	Δρmax = 0.27 e Å−3
15 restraints	Δρmin = −0.27 e Å−3

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
S1	0.56133 (7)	0.45061 (8)	0.61403 (3)	0.0699 (2)
O1	0.7192 (5)	0.2528 (4)	0.38302 (13)	0.1562 (12)
O2	0.7900 (2)	0.4795 (3)	0.48092 (11)	0.0856 (6)
O3A	0.7493 (19)	0.5809 (14)	0.8800 (8)	0.091 (3)	0.531 (9)
O4	1.1251 (2)	0.84381 (17)	0.77262 (11)	0.0811 (5)
N1	0.7598 (3)	0.3251 (3)	0.46237 (12)	0.0771 (6)
N2	0.84041 (19)	0.50765 (19)	0.76035 (9)	0.0551 (4)
N3	1.0289 (2)	0.56998 (19)	0.81531 (10)	0.0563 (4)
N4	1.6987 (2)	0.9892 (2)	0.90983 (13)	0.0741 (6)
C1	0.7803 (3)	0.2246 (3)	0.53763 (13)	0.0645 (6)
C2	0.7799 (4)	0.0637 (3)	0.5129 (2)	0.0927 (9)
C3	0.7969 (4)	−0.0385 (4)	0.5785 (3)	0.1087 (13)
C4	0.8097 (4)	0.0165 (3)	0.6687 (2)	0.0947 (10)
C5	0.8058 (3)	0.1748 (3)	0.69268 (15)	0.0707 (7)
C6	0.7942 (2)	0.2861 (2)	0.62885 (12)	0.0539 (5)
C7	0.7962 (2)	0.4616 (2)	0.65973 (11)	0.0527 (5)
C8A	0.5297 (5)	0.4937 (9)	0.7236 (2)	0.0587 (13)	0.531 (9)
C9A	0.7153 (13)	0.5370 (11)	0.7958 (6)	0.0610 (19)	0.531 (9)
C10A	0.3540 (12)	0.3317 (16)	0.7341 (6)	0.126 (4)	0.531 (9)
C11	1.1625 (3)	0.7433 (2)	0.81826 (12)	0.0567 (5)
C12	1.3603 (2)	0.7956 (2)	0.87999 (12)	0.0529 (5)
C13	1.3975 (3)	0.7257 (3)	0.95825 (13)	0.0648 (6)
C14	1.5852 (3)	0.7867 (3)	1.01129 (15)	0.0738 (7)
C15	1.7293 (3)	0.9187 (3)	0.98500 (15)	0.0681 (6)
C16	1.5163 (3)	0.9272 (2)	0.85835 (14)	0.0679 (6)
C8B	0.5041 (6)	0.3820 (10)	0.7244 (3)	0.0592 (16)	0.469 (9)
C9B	0.7003 (12)	0.4774 (11)	0.7995 (6)	0.0513 (16)	0.469 (9)
C10B	0.3623 (15)	0.4314 (15)	0.7441 (7)	0.093 (3)	0.469 (9)
O3B	0.7218 (17)	0.5168 (14)	0.8810 (8)	0.076 (2)	0.469 (9)
OW1	0.0315 (2)	0.3195 (2)	0.93103 (12)	0.0931 (6)
H4	0.82100	−0.05310	0.71360	0.1130*
H7	0.89160	0.56040	0.63860	0.0630*
H8A	0.50960	0.60000	0.72670	0.0710*	0.531 (9)
H5	0.81110	0.20840	0.75370	0.0850*
H10B	0.33860	0.35480	0.79400	0.1890*	0.531 (9)
H10C	0.37100	0.22610	0.72940	0.1890*	0.531 (9)
H13	1.29640	0.63760	0.97530	0.0780*
H14	1.61340	0.73910	1.06390	0.0890*
H15	1.85600	0.96150	1.02190	0.0820*
H16	1.49240	0.97470	0.80510	0.0810*
H10A	0.24130	0.31160	0.68570	0.1890*	0.531 (9)
HN1	1.048 (3)	0.499 (2)	0.8508 (13)	0.062 (5)*
H2	0.76800	0.02530	0.45140	0.1110*
H3	0.79980	−0.14520	0.56220	0.1300*
H8B	0.45250	0.25050	0.71860	0.0710*	0.469 (9)
H10D	0.24250	0.36760	0.69470	0.1400*	0.469 (9)
H10E	0.41040	0.55960	0.74800	0.1400*	0.469 (9)
H10F	0.34190	0.39900	0.80230	0.1400*	0.469 (9)
HW1	0.078 (4)	0.355 (4)	0.9872 (13)	0.120 (11)*
HW2	−0.068 (3)	0.230 (3)	0.924 (2)	0.126 (11)*

	U11	U22	U33	U12	U13	U23
S1	0.0665 (3)	0.1068 (4)	0.0450 (2)	0.0532 (3)	0.0084 (2)	0.0109 (2)
O1	0.245 (3)	0.159 (2)	0.0532 (10)	0.088 (2)	0.0453 (15)	0.0094 (12)
O2	0.0975 (11)	0.1172 (13)	0.0581 (8)	0.0619 (10)	0.0255 (8)	0.0329 (9)
O3A	0.103 (6)	0.130 (7)	0.046 (3)	0.069 (5)	0.009 (3)	−0.007 (4)
O4	0.0813 (9)	0.0583 (7)	0.0893 (10)	0.0317 (7)	0.0032 (8)	0.0239 (7)
N1	0.0713 (10)	0.1071 (14)	0.0478 (9)	0.0377 (10)	0.0208 (8)	0.0090 (9)
N2	0.0463 (7)	0.0679 (8)	0.0414 (7)	0.0231 (6)	0.0062 (5)	0.0082 (6)
N3	0.0466 (7)	0.0540 (7)	0.0549 (8)	0.0182 (6)	0.0038 (6)	0.0145 (6)
N4	0.0560 (9)	0.0652 (9)	0.0838 (12)	0.0139 (7)	0.0225 (8)	0.0155 (8)
C1	0.0540 (9)	0.0745 (11)	0.0580 (10)	0.0266 (8)	0.0150 (8)	0.0051 (8)
C2	0.0887 (16)	0.0873 (15)	0.0903 (17)	0.0380 (13)	0.0218 (13)	−0.0130 (13)
C3	0.114 (2)	0.0742 (15)	0.131 (3)	0.0498 (15)	0.0206 (19)	−0.0047 (16)
C4	0.0990 (18)	0.0634 (12)	0.107 (2)	0.0358 (12)	0.0121 (15)	0.0204 (12)
C5	0.0716 (12)	0.0611 (10)	0.0665 (12)	0.0247 (9)	0.0125 (9)	0.0166 (9)
C6	0.0446 (8)	0.0596 (9)	0.0512 (9)	0.0209 (7)	0.0117 (7)	0.0111 (7)
C7	0.0508 (8)	0.0626 (9)	0.0425 (8)	0.0253 (7)	0.0131 (6)	0.0155 (7)
C8A	0.061 (2)	0.071 (3)	0.0513 (18)	0.038 (2)	0.0153 (15)	0.0157 (17)
C9A	0.070 (3)	0.069 (4)	0.051 (3)	0.041 (3)	0.014 (2)	0.012 (3)
C10A	0.066 (4)	0.190 (9)	0.077 (5)	0.021 (5)	0.019 (3)	0.056 (6)
C11	0.0582 (9)	0.0502 (8)	0.0557 (9)	0.0233 (7)	0.0124 (8)	0.0097 (7)
C12	0.0519 (8)	0.0440 (7)	0.0542 (9)	0.0174 (6)	0.0135 (7)	0.0069 (6)
C13	0.0504 (9)	0.0669 (10)	0.0607 (10)	0.0152 (8)	0.0138 (8)	0.0192 (8)
C14	0.0571 (10)	0.0843 (13)	0.0658 (11)	0.0242 (9)	0.0118 (9)	0.0250 (10)
C15	0.0485 (9)	0.0713 (11)	0.0739 (12)	0.0220 (8)	0.0151 (9)	0.0082 (9)
C16	0.0628 (11)	0.0543 (9)	0.0709 (12)	0.0160 (8)	0.0168 (9)	0.0182 (8)
C8B	0.051 (2)	0.071 (4)	0.053 (2)	0.027 (2)	0.0144 (16)	0.017 (2)
C9B	0.050 (2)	0.065 (4)	0.039 (2)	0.027 (3)	0.0129 (16)	0.018 (3)
C10B	0.080 (5)	0.150 (8)	0.073 (3)	0.071 (6)	0.031 (3)	0.021 (5)
O3B	0.060 (2)	0.113 (6)	0.043 (3)	0.031 (4)	0.0160 (18)	0.015 (4)
OW1	0.0800 (10)	0.0681 (9)	0.0728 (10)	0.0017 (8)	−0.0099 (8)	0.0323 (8)

S1—C7	1.8238 (19)	C8A—C9A	1.501 (11)
S1—C8A	1.772 (4)	C8A—C10A	1.518 (14)
S1—C8B	1.880 (5)	C8B—C10B	1.476 (15)
O1—N1	1.205 (3)	C8B—C9B	1.529 (11)
O2—N1	1.211 (3)	C11—C12	1.495 (3)
O3A—C9A	1.226 (14)	C12—C16	1.384 (3)
O3B—C9B	1.201 (15)	C12—C13	1.370 (3)
O4—C11	1.211 (2)	C13—C14	1.374 (4)
OW1—HW1	0.813 (19)	C14—C15	1.365 (3)
OW1—HW2	0.80 (2)	C2—H2	0.9300
N1—C1	1.468 (3)	C3—H3	0.9300
N2—N3	1.386 (2)	C4—H4	0.9300
N2—C7	1.454 (2)	C5—H5	0.9300
N2—C9A	1.364 (11)	C7—H7	0.9800
N2—C9B	1.339 (10)	C8A—H8A	0.9800
N3—C11	1.360 (2)	C8B—H8B	0.9800
N4—C16	1.331 (3)	C10A—H10B	0.9600
N4—C15	1.324 (3)	C10A—H10C	0.9600
N3—HN1	0.861 (18)	C10A—H10A	0.9600
C1—C6	1.399 (3)	C10B—H10F	0.9600
C1—C2	1.383 (4)	C10B—H10E	0.9600
C2—C3	1.363 (5)	C10B—H10D	0.9600
C3—C4	1.373 (5)	C13—H13	0.9300
C4—C5	1.378 (4)	C14—H14	0.9300
C5—C6	1.390 (3)	C15—H15	0.9300
C6—C7	1.516 (2)	C16—H16	0.9300
S1···O2	2.999 (2)	C12···C15ix	3.496 (3)
S1···N1	3.466 (2)	C13···O3Bvi	3.288 (11)
S1···S1i	3.5774 (7)	C13···OW1vii	3.286 (3)
S1···O2i	3.188 (2)	C14···C12ix	3.586 (3)
O1···O4ii	3.150 (4)	C14···C16ix	3.523 (3)
O1···C11ii	3.389 (3)	C14···O3Avii	3.420 (15)
OW1···C13iii	3.286 (3)	C15···C12ix	3.496 (3)
OW1···N4iv	2.803 (2)	C15···O3Avii	3.266 (13)
OW1···O3Av	2.806 (12)	C16···C14ix	3.523 (3)
OW1···N3iii	2.804 (2)	C5···HN1	3.026 (17)
OW1···O3Bv	2.870 (12)	C9B···H5	2.9000
O2···C7	2.688 (2)	C10A···H14vi	3.0900
O2···S1i	3.188 (2)	C11···H7	2.8500
O2···N1ii	3.123 (3)	C12···H10Evii	2.9600
O2···S1	2.999 (2)	C13···HN1	2.62 (2)
O2···O2ii	3.177 (3)	C15···H15x	3.0900
O2···C1ii	3.348 (3)	C15···HW2viii	2.74 (2)
O3A···C15iii	3.266 (13)	C16···H10Evii	3.0700
O3A···C11	3.400 (16)	C16···HW2viii	3.04 (3)
O3A···C14iii	3.420 (15)	HN1···OW1vii	1.958 (17)
O3A···OW1v	2.806 (12)	HN1···C5	3.026 (17)
O3A···N3	2.720 (16)	HN1···H5	2.4100
O3B···OW1v	2.870 (12)	HN1···HW1vii	2.45 (3)
O3B···C13vi	3.288 (11)	HN1···HW2vii	2.46 (3)
O3B···N3	2.769 (15)	HN1···O3B	2.87 (3)
O4···C7	3.136 (2)	HN1···H13	2.1800
O4···C9A	3.288 (10)	HN1···C13	2.62 (2)
O4···O1ii	3.150 (4)	H2···O1	2.3600
O4···N2	2.689 (2)	HW1···H13iii	2.2900
O1···H10Ei	2.8800	HW1···O3Bv	2.09 (2)
O1···H8Ai	2.9200	HW1···O3Av	2.02 (2)
O1···H2	2.3600	HW1···HN1iii	2.45 (3)
OW1···H5iii	2.6600	HW2···C16iv	3.04 (3)
OW1···H13iii	2.4800	HW2···N4iv	2.01 (2)
OW1···HN1iii	1.958 (17)	HW2···C15iv	2.74 (2)
O2···H7	2.2600	HW2···H5iii	2.4700
O3A···H10B	2.8900	HW2···HN1iii	2.46 (3)
O3A···H13vi	2.9000	H5···HN1	2.4100
O3A···HW1v	2.02 (2)	H5···HW2vii	2.4700
O3B···H10F	2.7000	H5···OW1vii	2.6600
O3B···HN1	2.87 (3)	H5···N2	2.4100
O3B···H13vi	2.5800	H5···C9B	2.9000
O3B···HW1v	2.09 (3)	H5···N3	2.7000
O4···H7	2.6300	H7···O2	2.2600
O4···H16	2.5800	H7···O4	2.6300
N1···S1	3.466 (2)	H7···C11	2.8500
N1···O2ii	3.123 (3)	H7···N1	2.8700
N2···O4	2.689 (2)	H8A···O1i	2.9200
N3···O3B	2.769 (15)	H10B···O3A	2.8900
N3···OW1vii	2.804 (2)	H10B···H14vi	2.3200
N3···O3A	2.720 (16)	H10E···C12iii	2.9600
N3···C5	3.167 (3)	H10E···O1i	2.8800
N4···OW1viii	2.803 (2)	H10E···C16iii	3.0700
N1···H7	2.8700	H10F···H14vi	2.4100
N2···H5	2.4100	H10F···O3B	2.7000
N3···H13	2.6500	H13···OW1vii	2.4800
N3···H5	2.7000	H13···N3	2.6500
N4···HW2viii	2.01 (2)	H13···HN1	2.1800
C1···O2ii	3.348 (3)	H13···HW1vii	2.2900
C5···C9B	3.466 (10)	H13···O3Avi	2.9000
C5···N3	3.167 (3)	H13···O3Bvi	2.5800
C7···O2	2.688 (2)	H14···C10Avi	3.0900
C7···O4	3.136 (2)	H14···H10Bvi	2.3200
C9A···O4	3.288 (10)	H14···H10Fvi	2.4100
C9B···C5	3.466 (10)	H15···C15x	3.0900
C11···O3A	3.400 (16)	H15···H15x	2.4000
C11···O1ii	3.389 (3)	H16···O4	2.5800
C12···C14ix	3.586 (3)
C7—S1—C8A	96.72 (17)	C13—C12—C16	117.71 (19)
C7—S1—C8B	89.56 (19)	C11—C12—C13	124.34 (17)
HW1—OW1—HW2	105 (3)	C12—C13—C14	119.5 (2)
O1—N1—C1	118.6 (2)	C13—C14—C15	118.5 (2)
O2—N1—C1	120.00 (17)	N4—C15—C14	123.6 (2)
O1—N1—O2	121.4 (2)	N4—C16—C12	123.38 (17)
N3—N2—C9A	119.9 (4)	C3—C2—H2	120.00
N3—N2—C9B	120.7 (4)	C1—C2—H2	120.00
N3—N2—C7	118.23 (15)	C2—C3—H3	120.00
C7—N2—C9B	120.9 (4)	C4—C3—H3	120.00
C7—N2—C9A	119.4 (4)	C3—C4—H4	120.00
N2—N3—C11	118.67 (16)	C5—C4—H4	120.00
C15—N4—C16	117.28 (18)	C6—C5—H5	119.00
C11—N3—HN1	124.9 (14)	C4—C5—H5	119.00
N2—N3—HN1	115.9 (14)	N2—C7—H7	109.00
N1—C1—C2	116.4 (2)	C6—C7—H7	109.00
N1—C1—C6	121.7 (2)	S1—C7—H7	109.00
C2—C1—C6	121.9 (2)	S1—C8A—H8A	109.00
C1—C2—C3	120.1 (3)	C10A—C8A—H8A	109.00
C2—C3—C4	119.8 (3)	C9A—C8A—H8A	109.00
C3—C4—C5	120.0 (3)	C9B—C8B—H8B	109.00
C4—C5—C6	122.3 (2)	C10B—C8B—H8B	109.00
C5—C6—C7	120.07 (16)	S1—C8B—H8B	109.00
C1—C6—C7	124.04 (16)	H10A—C10A—H10B	109.00
C1—C6—C5	115.89 (18)	C8A—C10A—H10C	109.00
N2—C7—C6	113.13 (13)	C8A—C10A—H10B	110.00
S1—C7—N2	103.61 (12)	H10A—C10A—H10C	109.00
S1—C7—C6	112.56 (12)	H10B—C10A—H10C	109.00
C9A—C8A—C10A	114.1 (6)	C8A—C10A—H10A	110.00
S1—C8A—C9A	106.0 (5)	C8B—C10B—H10D	109.00
S1—C8A—C10A	109.8 (5)	C8B—C10B—H10E	109.00
C9B—C8B—C10B	113.3 (7)	H10D—C10B—H10F	110.00
S1—C8B—C10B	112.3 (5)	H10D—C10B—H10E	109.00
S1—C8B—C9B	104.0 (5)	H10E—C10B—H10F	110.00
N2—C9A—C8A	113.7 (6)	C8B—C10B—H10F	109.00
O3A—C9A—C8A	124.5 (12)	C14—C13—H13	120.00
O3A—C9A—N2	121.6 (11)	C12—C13—H13	120.00
O3B—C9B—C8B	124.1 (11)	C13—C14—H14	121.00
N2—C9B—C8B	109.7 (6)	C15—C14—H14	121.00
O3B—C9B—N2	126.2 (11)	N4—C15—H15	118.00
O4—C11—N3	122.8 (2)	C14—C15—H15	118.00
N3—C11—C12	113.92 (16)	N4—C16—H16	118.00
O4—C11—C12	123.26 (16)	C12—C16—H16	118.00
C11—C12—C16	117.92 (16)
C8A—S1—C7—C6	120.0 (2)	N1—C1—C2—C3	−179.5 (3)
C7—S1—C8A—C10A	−117.5 (5)	C2—C1—C6—C7	179.7 (2)
C7—S1—C8A—C9A	6.1 (5)	C1—C2—C3—C4	1.6 (5)
C8A—S1—C7—N2	−2.6 (2)	C2—C3—C4—C5	−0.2 (5)
O1—N1—C1—C6	−168.9 (3)	C3—C4—C5—C6	−1.7 (5)
O1—N1—C1—C2	9.5 (4)	C4—C5—C6—C1	2.0 (4)
O2—N1—C1—C2	−168.0 (3)	C4—C5—C6—C7	−178.2 (2)
O2—N1—C1—C6	13.7 (4)	C5—C6—C7—N2	8.9 (3)
C9A—N2—N3—C11	−86.1 (5)	C1—C6—C7—S1	71.6 (2)
N3—N2—C7—S1	−164.40 (12)	C5—C6—C7—S1	−108.16 (19)
C7—N2—N3—C11	75.9 (2)	C1—C6—C7—N2	−171.39 (19)
C9A—N2—C7—C6	−124.5 (4)	C10A—C8A—C9A—N2	112.4 (7)
C9A—N2—C7—S1	−2.3 (4)	S1—C8A—C9A—N2	−8.5 (7)
N3—N2—C7—C6	73.41 (19)	C10A—C8A—C9A—O3A	−62.0 (12)
C7—N2—C9A—C8A	7.4 (8)	S1—C8A—C9A—O3A	177.1 (9)
N3—N2—C9A—O3A	−16.3 (11)	N3—C11—C12—C13	−30.2 (3)
C7—N2—C9A—O3A	−178.0 (8)	O4—C11—C12—C13	152.0 (2)
N3—N2—C9A—C8A	169.1 (4)	O4—C11—C12—C16	−26.0 (3)
N2—N3—C11—C12	179.78 (15)	N3—C11—C12—C16	151.82 (18)
N2—N3—C11—O4	−2.4 (3)	C16—C12—C13—C14	−0.4 (3)
C16—N4—C15—C14	0.6 (3)	C11—C12—C16—N4	177.67 (18)
C15—N4—C16—C12	0.4 (3)	C11—C12—C13—C14	−178.5 (2)
N1—C1—C6—C5	177.7 (2)	C13—C12—C16—N4	−0.5 (3)
N1—C1—C6—C7	−2.1 (3)	C12—C13—C14—C15	1.3 (3)
C6—C1—C2—C3	−1.2 (5)	C13—C14—C15—N4	−1.4 (4)
C2—C1—C6—C5	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—HN1···OW1vii	0.86 (2)	1.96 (2)	2.804 (2)	167 (2)
OW1—HW1···O3Av	0.81 (2)	2.02 (2)	2.806 (1)	163 (4)
OW1—HW2···N4iv	0.80 (2)	2.01 (2)	2.803 (2)	173 (3)
C5—H5···N2	0.93	2.41	2.794 (3)	104.
C7—H7···O2	0.98	2.26	2.688 (2)	105.
C13—H13···OW1vii	0.93	2.48	3.286 (3)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—HN1⋯OW1i	0.86 (2)	1.96 (2)	2.804 (2)	167 (2)
OW1—HW1⋯O3Aii	0.81 (2)	2.02 (2)	2.806 (1)	163 (4)
OW1—HW2⋯N4iii	0.80 (2)	2.01 (2)	2.803 (2)	173 (3)

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