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

In the title compound, C(16)H(14)BrN(3)O(2)S, the atoms of the 1,3-thia-zolidine group, except for the N and the C atoms attached to the bromo-benzene ring, are disordered over two sets of sites with occupancies of 0.605 (13) and 0.395 (13). The benzene and pyridine rings make a dihedral angle of 86.2 (2)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, forming a three-dimensional network. Furthermore, there is a π-π stacking inter-action [centroid-centroid distance = 3.758 (2) Å] between the pyridine and benzene rings.

Related literature

For the diverse pharmacological properties of pyridine-3-carboxamides, see: Abdel-Alim et al. (2005 ▶); Girgis et al. (2006 ▶); Slominska et al. (2008 ▶); Spanka et al. (2010 ▶); activities. For the pharmacological properties of 4-thia­zolidinone deriv­atives, see: Vigorita et al. (1992 ▶); Barreca et al. (2003 ▶); Rao et al. (2004 ▶); Jacop & Kutty (2004 ▶); Kalia et al. (2007 ▶).

Experimental

Crystal data

C16H14BrN3O2S

M = 392.27

Tetragonal,

a = 24.5799 (8) Å

c = 10.9601 (6) Å

V = 6621.8 (5) Å3

Z = 16

Mo Kα radiation

μ = 2.62 mm−1

T = 296 K

0.37 × 0.30 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.444, T max = 0.527

13377 measured reflections

3644 independent reflections

1834 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.119

S = 1.02

3644 reflections

259 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.34 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/S1600536811009603/om2414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009603/om2414Isup2.hkl

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

C16H14BrN3O2S	Dx = 1.574 Mg m−3
Mr = 392.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 9828 reflections
Hall symbol: -I 4ad	θ = 1.7–27.6°
a = 24.5799 (8) Å	µ = 2.62 mm−1
c = 10.9601 (6) Å	T = 296 K
V = 6621.8 (5) Å3	Block, colourless
Z = 16	0.37 × 0.30 × 0.28 mm
F(000) = 3168

Stoe IPDS 2 diffractometer	3644 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1834 reflections with I > 2σ(I)
plane graphite	Rint = 0.055
Detector resolution: 6.67 pixels mm-1	θmax = 27.1°, θmin = 1.7°
ω scans	h = −31→21
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −31→31
Tmin = 0.444, Tmax = 0.527	l = −14→9
13377 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3
3644 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 0.39 e Å−3
13 restraints	Δρmin = −0.34 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)
Br1	0.16970 (2)	0.06678 (2)	0.30959 (7)	0.1147 (3)
S1A	0.2142 (3)	0.3258 (3)	0.5735 (10)	0.112 (3)	0.605 (13)
O1A	0.3622 (6)	0.3685 (8)	0.529 (2)	0.106 (7)	0.605 (13)
O2	0.36844 (13)	0.25700 (14)	0.7196 (3)	0.0950 (14)
N1	0.31204 (11)	0.29058 (12)	0.5238 (3)	0.0623 (13)
N2	0.35645 (13)	0.25553 (13)	0.5165 (3)	0.0595 (11)
N3	0.48519 (14)	0.14473 (13)	0.4828 (4)	0.0707 (14)
C1	0.20330 (14)	0.18614 (15)	0.5608 (4)	0.0640 (14)
C2	0.18240 (16)	0.14118 (16)	0.5027 (5)	0.0730 (16)
C3	0.19861 (16)	0.12919 (15)	0.3869 (5)	0.0673 (18)
C4	0.23459 (18)	0.16225 (18)	0.3269 (4)	0.0763 (17)
C5	0.25484 (16)	0.20793 (16)	0.3847 (4)	0.0653 (16)
C6	0.23981 (14)	0.22004 (14)	0.5022 (4)	0.0560 (14)
C7	0.26058 (14)	0.26964 (15)	0.5686 (4)	0.0703 (16)
C8A	0.2692 (4)	0.3725 (3)	0.5910 (13)	0.075 (4)	0.605 (13)
C9A	0.3197 (5)	0.3447 (3)	0.548 (2)	0.079 (8)	0.605 (13)
C10A	0.2598 (5)	0.4271 (4)	0.5333 (15)	0.125 (7)	0.605 (13)
C11	0.38243 (15)	0.24133 (15)	0.6199 (5)	0.0603 (14)
C12	0.42975 (14)	0.20345 (14)	0.6039 (4)	0.0510 (14)
C13	0.46220 (17)	0.19258 (16)	0.7037 (4)	0.0673 (16)
C14	0.50564 (16)	0.15811 (16)	0.6913 (5)	0.0713 (18)
C15	0.51542 (16)	0.13554 (16)	0.5804 (5)	0.0663 (16)
C16	0.44267 (16)	0.17785 (16)	0.4962 (4)	0.0630 (14)
O1B	0.3661 (9)	0.3633 (10)	0.482 (3)	0.077 (6)	0.395 (13)
C8B	0.2702 (5)	0.3783 (5)	0.5205 (14)	0.063 (5)	0.395 (13)
S1B	0.2171 (4)	0.3287 (4)	0.5249 (11)	0.078 (2)	0.395 (13)
C10B	0.2737 (7)	0.4152 (8)	0.6288 (16)	0.100 (7)	0.395 (13)
C9B	0.3209 (8)	0.3454 (4)	0.508 (3)	0.059 (7)	0.395 (13)
H5	0.27890	0.23070	0.34360	0.0780*
H7	0.26680	0.25850	0.65330	0.0840*
H4	0.24530	0.15400	0.24770	0.0910*
H10A	0.22620	0.44200	0.56260	0.1870*	0.605 (13)
H10B	0.25810	0.42300	0.44630	0.1870*	0.605 (13)
H8A	0.27360	0.37870	0.67870	0.07 (2)*	0.605 (13)
H13	0.45460	0.20850	0.77870	0.0810*
H14	0.52800	0.15030	0.75750	0.0850*
H15	0.54510	0.11230	0.57270	0.0800*
H16	0.42050	0.18400	0.42880	0.0760*
H1	0.19280	0.19380	0.64040	0.0770*
HN2	0.3657 (17)	0.2533 (17)	0.4409 (14)	0.0810*
H10C	0.28920	0.45110	0.55420	0.1870*	0.605 (13)
H2A	0.15730	0.11910	0.54230	0.0870*
H8B	0.26570	0.40050	0.44690	0.0750*	0.395 (13)
H10D	0.24060	0.43570	0.63580	0.1500*	0.395 (13)
H10E	0.30370	0.43980	0.61860	0.1500*	0.395 (13)
H10F	0.27900	0.39400	0.70120	0.1500*	0.395 (13)

	U11	U22	U33	U12	U13	U23
Br1	0.1245 (5)	0.0791 (3)	0.1405 (6)	−0.0194 (3)	−0.0237 (4)	−0.0275 (3)
S1A	0.0607 (18)	0.092 (3)	0.183 (8)	−0.0045 (15)	0.027 (3)	−0.069 (3)
O1A	0.066 (5)	0.084 (5)	0.167 (19)	−0.012 (4)	0.003 (7)	−0.028 (8)
O2	0.094 (2)	0.131 (3)	0.060 (2)	0.0395 (19)	0.0025 (17)	−0.029 (2)
N1	0.0498 (17)	0.0572 (18)	0.080 (3)	0.0016 (14)	0.0006 (16)	−0.0031 (17)
N2	0.0555 (18)	0.071 (2)	0.052 (2)	0.0053 (15)	0.0044 (18)	−0.0008 (19)
N3	0.076 (2)	0.074 (2)	0.062 (3)	0.0162 (18)	0.013 (2)	0.0013 (19)
C1	0.060 (2)	0.070 (2)	0.062 (3)	0.0051 (19)	0.014 (2)	−0.001 (2)
C2	0.061 (2)	0.059 (2)	0.099 (4)	−0.0032 (19)	0.004 (3)	0.009 (2)
C3	0.069 (3)	0.055 (2)	0.078 (4)	0.0041 (19)	−0.010 (2)	−0.005 (2)
C4	0.090 (3)	0.082 (3)	0.057 (3)	−0.004 (2)	0.002 (2)	−0.010 (3)
C5	0.070 (3)	0.068 (2)	0.058 (3)	−0.0105 (19)	0.004 (2)	0.003 (2)
C6	0.051 (2)	0.057 (2)	0.060 (3)	0.0035 (17)	0.003 (2)	−0.005 (2)
C7	0.059 (2)	0.077 (3)	0.075 (3)	−0.0095 (18)	0.009 (2)	−0.016 (2)
C8A	0.083 (6)	0.065 (6)	0.076 (10)	0.000 (4)	0.005 (7)	−0.012 (6)
C9A	0.050 (7)	0.076 (8)	0.11 (2)	−0.008 (5)	−0.009 (6)	−0.003 (5)
C10A	0.139 (9)	0.073 (7)	0.162 (16)	0.020 (6)	−0.004 (9)	−0.001 (8)
C11	0.061 (2)	0.067 (2)	0.053 (3)	0.0035 (18)	0.004 (2)	−0.007 (2)
C12	0.057 (2)	0.053 (2)	0.043 (3)	−0.0029 (16)	0.0041 (19)	−0.0006 (18)
C13	0.082 (3)	0.069 (2)	0.051 (3)	0.004 (2)	−0.006 (2)	−0.007 (2)
C14	0.070 (3)	0.066 (2)	0.078 (4)	0.008 (2)	−0.017 (2)	0.000 (3)
C15	0.061 (2)	0.060 (2)	0.078 (4)	0.0060 (18)	0.007 (2)	0.002 (2)
C16	0.070 (2)	0.070 (2)	0.049 (3)	0.012 (2)	0.003 (2)	−0.002 (2)
O1B	0.073 (8)	0.063 (9)	0.096 (14)	−0.008 (6)	0.006 (7)	0.010 (9)
C8B	0.072 (7)	0.063 (8)	0.053 (10)	0.008 (5)	0.001 (8)	0.012 (8)
S1B	0.049 (3)	0.069 (3)	0.115 (6)	0.0113 (17)	0.007 (3)	−0.030 (3)
C10B	0.110 (11)	0.078 (11)	0.112 (15)	−0.013 (8)	−0.001 (10)	−0.020 (11)
C9B	0.069 (12)	0.057 (10)	0.052 (14)	0.006 (8)	−0.001 (7)	−0.004 (6)

Br1—C3	1.891 (4)	C8B—C9B	1.49 (2)
S1A—C7	1.791 (8)	C8B—C10B	1.50 (2)
S1A—C8A	1.784 (12)	C11—C12	1.500 (5)
S1B—C7	1.865 (11)	C12—C13	1.380 (6)
S1B—C8B	1.787 (16)	C12—C16	1.375 (6)
O1A—C9A	1.22 (2)	C13—C14	1.370 (6)
O1B—C9B	1.23 (3)	C14—C15	1.358 (7)
O2—C11	1.209 (6)	C1—H1	0.9300
N1—C9A	1.370 (9)	C2—H2A	0.9300
N1—N2	1.393 (4)	C4—H4	0.9300
N1—C7	1.451 (5)	C5—H5	0.9300
N1—C9B	1.376 (11)	C7—H7	0.9800
N2—C11	1.347 (6)	C8A—H8A	0.9800
N3—C15	1.322 (6)	C8B—H8B	0.9800
N3—C16	1.333 (5)	C10A—H10B	0.9600
N2—HN2	0.861 (19)	C10A—H10C	0.9600
C1—C6	1.383 (5)	C10A—H10A	0.9600
C1—C2	1.375 (6)	C10B—H10F	0.9600
C2—C3	1.363 (7)	C10B—H10D	0.9600
C3—C4	1.369 (6)	C10B—H10E	0.9600
C4—C5	1.382 (6)	C13—H13	0.9300
C5—C6	1.372 (6)	C14—H14	0.9300
C6—C7	1.509 (5)	C15—H15	0.9300
C8A—C9A	1.493 (16)	C16—H16	0.9300
C8A—C10A	1.502 (14)
Br1···C2i	3.679 (4)	C14···C1vii	3.483 (6)
Br1···C3i	3.669 (4)	C15···O1Aiii	3.062 (16)
S1B···C15i	3.651 (12)	C15···O1Biii	3.11 (2)
S1B···C14i	3.679 (11)	C15···S1Bvii	3.651 (12)
S1A···H14i	3.1300	C16···O1Bvi	3.23 (3)
S1B···H15i	3.0700	C5···H5ii	3.0400
S1B···H14i	3.1500	C5···HN2	3.01 (4)
S1B···H4ii	3.1600	C8B···H10Eviii	3.0800
O1A···N2	2.78 (2)	C8B···H4ii	3.0700
O1A···C15iii	3.062 (16)	C10A···H10Cviii	3.0100
O1A···C11	3.32 (2)	C11···H7	2.9000
O1B···N2	2.69 (2)	C15···HN2vi	3.048 (18)
O1B···C11	3.38 (3)	C16···HN2	2.72 (4)
O1B···C16iv	3.23 (3)	C16···HN2vi	2.88 (3)
O1B···C15iii	3.11 (2)	H1···O2v	2.4700
O2···N1	2.685 (5)	H1···H7	2.4200
O2···C7	3.141 (5)	HN2···C16	2.72 (4)
O2···C9A	3.102 (15)	HN2···H16	2.1800
O2···C1v	3.295 (5)	HN2···C5	3.01 (4)
O2···C9B	3.39 (2)	HN2···N3iv	2.05 (2)
O1A···H15iii	2.3800	HN2···C15iv	3.048 (18)
O1A···H10C	2.7200	HN2···O1B	2.74 (5)
O1B···H10E	2.8500	HN2···C16iv	2.88 (3)
O1B···H15iii	2.4700	HN2···H5	2.4500
O1B···HN2	2.74 (5)	H4···S1Bii	3.1600
O1B···H16iv	2.5700	H4···H8Bii	2.5300
O2···H1v	2.4700	H4···C8Bii	3.0700
O2···H7	2.6000	H5···C5ii	3.0400
O2···H13	2.5200	H5···HN2	2.4500
N1···O2	2.685 (5)	H5···N1	2.5900
N2···N3iv	2.899 (5)	H5···N2	2.7600
N2···O1A	2.78 (2)	H7···C11	2.9000
N2···C5	3.113 (5)	H7···H1	2.4200
N2···O1B	2.69 (2)	H7···O2	2.6000
N3···N2vi	2.899 (5)	H7···H7v	2.3100
N1···H5	2.5900	H8B···H10Eviii	2.3400
N2···H16	2.5500	H8B···H4ii	2.5300
N2···H5	2.7600	H10B···H10Cviii	2.2900
N3···HN2vi	2.05 (2)	H10C···O1A	2.7200
N3···H16vi	2.7400	H10C···H10Bix	2.2900
C1···C14i	3.483 (6)	H10C···C10Aix	3.0100
C1···O2v	3.295 (5)	H10E···C8Bix	3.0800
C2···C13i	3.574 (6)	H10E···O1B	2.8500
C2···Br1vii	3.679 (4)	H10E···H8Bix	2.3400
C3···Br1vii	3.669 (4)	H13···O2	2.5200
C5···N2	3.113 (5)	H14···S1Avii	3.1300
C7···O2	3.141 (5)	H14···S1Bvii	3.1500
C9A···O2	3.102 (15)	H15···O1Biii	2.4700
C9B···O2	3.39 (2)	H15···S1Bvii	3.0700
C11···O1A	3.32 (2)	H15···O1Aiii	2.3800
C11···O1B	3.38 (3)	H16···N2	2.5500
C13···C13iii	3.380 (6)	H16···N3iv	2.7400
C13···C2vii	3.574 (6)	H16···O1Bvi	2.5700
C14···S1Bvii	3.679 (11)	H16···HN2	2.1800
C7—S1A—C8A	91.0 (4)	C11—C12—C13	118.4 (4)
C7—S1B—C8B	96.9 (6)	C12—C13—C14	119.5 (4)
N2—N1—C9A	120.3 (6)	C13—C14—C15	118.7 (4)
N2—N1—C9B	118.3 (9)	N3—C15—C14	123.7 (4)
C7—N1—C9A	113.5 (7)	N3—C16—C12	123.7 (4)
C7—N1—C9B	121.9 (9)	C2—C1—H1	120.00
N2—N1—C7	118.9 (3)	C6—C1—H1	120.00
N1—N2—C11	118.9 (3)	C1—C2—H2A	120.00
C15—N3—C16	117.1 (4)	C3—C2—H2A	120.00
C11—N2—HN2	132 (3)	C3—C4—H4	120.00
N1—N2—HN2	108 (3)	C5—C4—H4	120.00
C2—C1—C6	120.8 (4)	C4—C5—H5	120.00
C1—C2—C3	119.7 (4)	C6—C5—H5	120.00
Br1—C3—C4	120.6 (4)	S1A—C7—H7	107.00
Br1—C3—C2	118.9 (3)	N1—C7—H7	106.00
C2—C3—C4	120.5 (4)	C6—C7—H7	106.00
C3—C4—C5	119.7 (4)	S1B—C7—H7	123.00
C4—C5—C6	120.6 (4)	S1A—C8A—H8A	107.00
C1—C6—C7	118.9 (4)	C9A—C8A—H8A	107.00
C1—C6—C5	118.7 (4)	C10A—C8A—H8A	107.00
C5—C6—C7	122.5 (3)	C9B—C8B—H8B	109.00
N1—C7—C6	114.7 (3)	C10B—C8B—H8B	109.00
S1A—C7—C6	115.0 (4)	S1B—C8B—H8B	109.00
S1B—C7—N1	97.9 (4)	C8A—C10A—H10C	109.00
S1B—C7—C6	108.1 (4)	H10A—C10A—H10B	110.00
S1A—C7—N1	107.0 (4)	H10B—C10A—H10C	110.00
S1A—C8A—C9A	107.6 (7)	C8A—C10A—H10B	109.00
C9A—C8A—C10A	113.8 (11)	H10A—C10A—H10C	109.00
S1A—C8A—C10A	114.4 (9)	C8A—C10A—H10A	109.00
S1B—C8B—C10B	115.7 (11)	H10D—C10B—H10F	110.00
C9B—C8B—C10B	110.7 (15)	C8B—C10B—H10D	109.00
S1B—C8B—C9B	104.1 (9)	C8B—C10B—H10E	109.00
N1—C9A—C8A	113.0 (8)	C8B—C10B—H10F	110.00
O1A—C9A—C8A	123.3 (11)	H10D—C10B—H10E	109.00
O1A—C9A—N1	123.6 (14)	H10E—C10B—H10F	110.00
N1—C9B—C8B	112.8 (14)	C14—C13—H13	120.00
O1B—C9B—C8B	125.6 (15)	C12—C13—H13	120.00
O1B—C9B—N1	121.5 (17)	C15—C14—H14	121.00
O2—C11—N2	122.9 (4)	C13—C14—H14	121.00
O2—C11—C12	121.6 (4)	N3—C15—H15	118.00
N2—C11—C12	115.5 (4)	C14—C15—H15	118.00
C13—C12—C16	117.3 (3)	C12—C16—H16	118.00
C11—C12—C16	124.3 (4)	N3—C16—H16	118.00
C8A—S1A—C7—N1	−26.3 (7)	C2—C3—C4—C5	0.4 (6)
C8A—S1A—C7—C6	−154.9 (6)	Br1—C3—C4—C5	179.4 (3)
C7—S1A—C8A—C9A	19.9 (12)	C3—C4—C5—C6	0.9 (6)
C7—S1A—C8A—C10A	147.4 (10)	C4—C5—C6—C7	−179.6 (4)
C7—N1—N2—C11	−75.1 (4)	C4—C5—C6—C1	−1.1 (6)
C9A—N1—N2—C11	73.1 (11)	C5—C6—C7—N1	−24.1 (5)
C9A—N1—C7—S1A	26.8 (10)	C5—C6—C7—S1A	100.6 (5)
N2—N1—C7—C6	−54.3 (5)	C1—C6—C7—N1	157.4 (3)
C9A—N1—C7—C6	155.5 (9)	C1—C6—C7—S1A	−77.9 (5)
C7—N1—C9A—C8A	−12.1 (17)	C10A—C8A—C9A—N1	−136.2 (13)
N2—N1—C9A—O1A	23 (3)	S1A—C8A—C9A—N1	−8.3 (18)
C7—N1—C9A—O1A	172.4 (18)	C10A—C8A—C9A—O1A	39 (3)
N2—N1—C9A—C8A	−161.9 (10)	S1A—C8A—C9A—O1A	167 (2)
N2—N1—C7—S1A	177.0 (4)	N2—C11—C12—C13	172.2 (3)
N1—N2—C11—O2	1.2 (6)	O2—C11—C12—C13	−9.0 (6)
N1—N2—C11—C12	180.0 (3)	O2—C11—C12—C16	169.8 (4)
C16—N3—C15—C14	−0.5 (6)	N2—C11—C12—C16	−9.0 (5)
C15—N3—C16—C12	1.6 (6)	C16—C12—C13—C14	1.0 (6)
C2—C1—C6—C7	178.5 (3)	C11—C12—C16—N3	179.2 (4)
C2—C1—C6—C5	0.0 (6)	C11—C12—C13—C14	180.0 (4)
C6—C1—C2—C3	1.3 (6)	C13—C12—C16—N3	−1.9 (6)
C1—C2—C3—C4	−1.5 (6)	C12—C13—C14—C15	−0.1 (6)
C1—C2—C3—Br1	179.5 (3)	C13—C14—C15—N3	−0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···N3iv	0.861 (19)	2.05 (2)	2.899 (5)	167 (4)
C1—H1···O2v	0.93	2.47	3.295 (5)	149
C5—H5···N1	0.93	2.59	2.903 (5)	100
C15—H15···O1Aiii	0.93	2.38	3.062 (16)	130
C16—H16···N2	0.93	2.55	2.861 (5)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯N3i	0.861 (19)	2.05 (2)	2.899 (5)	167 (4)
C1—H1⋯O2ii	0.93	2.47	3.295 (5)	149
C15—H15⋯O1Aiii	0.93	2.38	3.062 (16)	130

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