(4S)-4-Benzyl-N-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]sulfon-yl}-2-oxo-1,3-oxazolidine-3-carboxamide.

The title compound, C(21)H(21)N(3)O(7)S, contains an oxazolidinone ring and a sulfonamide group, both characteristic for biologically and pharrmaceutically active compounds. Both stereogenic centres reveal an S absolute configuration. The two oxazolidinone rings are in an envelope conformation with the methyl-ene carbon flap atoms deviating by 0.428 (1) and 0.364 (2) Å from the best least-square planes formed by the four other ring atoms. An intra-molecular N-H⋯O hydrogen bond contributes to the folded conformation of the mol-ecule. In the crystal, weak inter-molecular C-H⋯O inter-actions connect the mol-ecules into helices along the the twofold screw axes.

Related literature

For the biological activity of sulfonamides, see: Gayathri et al. (2006 ▶); Supuran et al. (2003 ▶); Kang & Reynolds (2009 ▶); Bouasla et al. (2010 ▶). For heterocyclic sulfonamide derivatives, see: Yan et al. (2007 ▶); Naganawa et al. (2006 ▶). For their use in coordination chemistry, see: King & Burgen (1976 ▶); Beloso et al. (2005 ▶). For hydrogen bonding, see: Adsmond & Grant (2001 ▶); Bernstein et al. (1995 ▶). For related structures, see: Michaux et al. (2001 ▶); Cheng et al. (2005 ▶); Benali-Cherif et al.(2002 ▶).

Experimental

Crystal data

C21H21N3O7S

M = 459.48

Monoclinic,

a = 10.4262 (3) Å

b = 9.7171 (2) Å

c = 10.7402 (2) Å

β = 101.504 (2)°

V = 1066.26 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.2 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

17946 measured reflections

5245 independent reflections

3795 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 1.00

5245 reflections

289 parameters

1 restraint

H-atom parameters constraned

Δρmax = 0.24 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1981 Friedel pairs

Flack parameter: 0.06 (8)

Data collection: KappaCCD Server Software (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020866/kp2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020866/kp2261Isup2.hkl

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

C21H21N3O7S	F(000) = 480
Mr = 459.48	Dx = 1.431 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.4262 (3) Å	Cell parameters from 3258 reflections
b = 9.7171 (2) Å	θ = 2.5–30.0°
c = 10.7402 (2) Å	µ = 0.20 mm−1
β = 101.504 (2)°	T = 293 K
V = 1066.26 (4) Å3	Prism, yellow
Z = 2	0.2 × 0.1 × 0.1 mm

Nonius KappaCCD diffractometer	3795 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.096
graphite	θmax = 30.0°, θmin = 2.5°
ω – θ scans	h = −14→12
17946 measured reflections	k = −9→13
5245 independent reflections	l = −15→15

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0929P)2 + 0.0529P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
5245 reflections	Δρmax = 0.24 e Å−3
289 parameters	Δρmin = −0.47 e Å−3
1 restraint	Absolute structure: Flack (1983), 1981 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (8)

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.

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	1.11803 (6)	0.79846 (7)	1.11762 (6)	0.04863 (18)
N2B	1.25586 (19)	0.7726 (2)	1.06927 (19)	0.0437 (5)
C5B	1.5343 (2)	0.8050 (3)	1.2204 (2)	0.0487 (5)
O2	1.1209 (2)	0.9380 (3)	1.1528 (2)	0.0654 (6)
O1B	1.3838 (2)	0.6678 (2)	0.9587 (2)	0.0627 (6)
O2A	0.7466 (2)	0.7106 (2)	0.9147 (2)	0.0630 (6)
O1A	0.66210 (19)	0.8112 (3)	0.7296 (2)	0.0747 (7)
O2B	1.2389 (3)	0.5376 (3)	1.0322 (3)	0.0775 (7)
O3	1.08127 (19)	0.9126 (2)	0.85647 (19)	0.0569 (5)
O1	1.0989 (2)	0.6947 (3)	1.2046 (2)	0.0722 (7)
N1A	0.87763 (19)	0.8226 (2)	0.7943 (2)	0.0471 (5)
C4B	1.4444 (3)	0.9200 (3)	1.1659 (3)	0.0522 (6)
H42B	1.4970	0.9965	1.1468	0.063*
H41B	1.3973	0.9508	1.2301	0.063*
C1	0.9943 (2)	0.8416 (3)	0.8803 (3)	0.0444 (5)
C3B	1.3446 (2)	0.8833 (3)	1.0456 (3)	0.0482 (6)
H3B	1.2943	0.9649	1.0118	0.058*
C3A	0.8541 (3)	0.8789 (4)	0.6648 (3)	0.0565 (7)
H3A	0.9046	0.9633	0.6611	0.068*
C2B	1.4016 (3)	0.8134 (4)	0.9414 (3)	0.0603 (7)
H22B	1.3556	0.8427	0.8581	0.072*
H21B	1.4937	0.8354	0.9502	0.072*
C6B	1.6509 (3)	0.7814 (4)	1.1794 (3)	0.0596 (7)
H6B	1.6745	0.8411	1.1201	0.071*
C1A	0.7615 (3)	0.7751 (3)	0.8242 (3)	0.0542 (7)
C1B	1.2861 (3)	0.6467 (3)	1.0213 (3)	0.0517 (6)
C5A	1.0220 (3)	0.7315 (3)	0.5809 (3)	0.0584 (7)
C10B	1.5048 (3)	0.7145 (4)	1.3092 (3)	0.0664 (9)
H10B	1.4289	0.7271	1.3410	0.080*
C2A	0.7090 (3)	0.9099 (5)	0.6474 (4)	0.0745 (10)
H21A	0.6946	1.0035	0.6729	0.089*
H22A	0.6653	0.8972	0.5596	0.089*
C7B	1.7327 (3)	0.6731 (4)	1.2235 (3)	0.0658 (8)
H7B	1.8104	0.6614	1.1947	0.079*
C4A	0.8813 (3)	0.7738 (5)	0.5683 (3)	0.0721 (9)
H41A	0.8298	0.6921	0.5754	0.087*
H42A	0.8512	0.8113	0.4839	0.087*
C6A	1.0983 (4)	0.7965 (5)	0.5074 (3)	0.0786 (10)
H6A	1.0616	0.8640	0.4498	0.094*
C9B	1.5884 (4)	0.6031 (5)	1.3526 (4)	0.0823 (12)
H9B	1.5669	0.5419	1.4118	0.099*
C10A	1.0801 (5)	0.6306 (4)	0.6632 (4)	0.0861 (12)
H10A	1.0311	0.5835	0.7130	0.103*
C8A	1.2831 (6)	0.6652 (11)	0.5994 (8)	0.141 (3)
H8A	1.3709	0.6431	0.6055	0.169*
C9A	1.2111 (8)	0.5991 (7)	0.6722 (6)	0.126 (3)
H9A	1.2499	0.5317	0.7290	0.151*
C8B	1.7004 (4)	0.5848 (4)	1.3079 (4)	0.0740 (9)
H8B	1.7547	0.5105	1.3360	0.089*
C7A	1.2278 (6)	0.7624 (8)	0.5188 (6)	0.118 (2)
H7A	1.2780	0.8080	0.4692	0.141*
N1	1.0021 (2)	0.7704 (3)	0.9924 (2)	0.0512 (5)
H1N	0.9439	0.7089	0.9970	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0478 (3)	0.0557 (4)	0.0443 (3)	−0.0059 (3)	0.0135 (2)	−0.0030 (3)
N2B	0.0420 (9)	0.0395 (12)	0.0494 (10)	−0.0003 (8)	0.0089 (8)	−0.0003 (9)
C5B	0.0451 (11)	0.0479 (14)	0.0513 (12)	−0.0111 (12)	0.0056 (9)	−0.0086 (13)
O2	0.0560 (11)	0.0671 (14)	0.0769 (13)	−0.0016 (10)	0.0222 (10)	−0.0215 (12)
O1B	0.0726 (13)	0.0603 (13)	0.0580 (11)	0.0165 (10)	0.0196 (10)	−0.0061 (10)
O2A	0.0549 (12)	0.0544 (13)	0.0836 (15)	−0.0101 (9)	0.0232 (10)	−0.0051 (12)
O1A	0.0402 (9)	0.0917 (18)	0.0871 (15)	0.0001 (11)	0.0006 (9)	−0.0081 (15)
O2B	0.108 (2)	0.0414 (12)	0.0823 (16)	−0.0072 (12)	0.0179 (14)	−0.0036 (11)
O3	0.0456 (9)	0.0636 (14)	0.0597 (10)	−0.0092 (9)	0.0065 (8)	0.0109 (10)
O1	0.0742 (14)	0.0918 (19)	0.0524 (11)	−0.0146 (13)	0.0167 (10)	0.0165 (12)
N1A	0.0408 (9)	0.0505 (14)	0.0499 (10)	−0.0014 (9)	0.0086 (8)	−0.0058 (10)
C4B	0.0468 (13)	0.0416 (14)	0.0707 (16)	−0.0057 (11)	0.0178 (12)	−0.0073 (13)
C1	0.0430 (11)	0.0410 (13)	0.0496 (13)	−0.0016 (9)	0.0101 (9)	−0.0027 (10)
C3B	0.0471 (12)	0.0396 (14)	0.0603 (15)	0.0015 (11)	0.0163 (11)	0.0037 (12)
C3A	0.0529 (14)	0.0639 (19)	0.0493 (14)	0.0022 (13)	0.0022 (11)	−0.0019 (13)
C2B	0.0613 (14)	0.067 (2)	0.0560 (14)	0.0092 (14)	0.0208 (11)	0.0117 (15)
C6B	0.0529 (13)	0.068 (2)	0.0583 (14)	0.0038 (14)	0.0119 (11)	−0.0068 (16)
C1A	0.0407 (12)	0.0506 (17)	0.0720 (16)	−0.0042 (11)	0.0126 (11)	−0.0146 (15)
C1B	0.0633 (15)	0.0403 (15)	0.0494 (13)	0.0066 (12)	0.0066 (11)	0.0001 (11)
C5A	0.0730 (18)	0.0586 (18)	0.0410 (12)	0.0076 (14)	0.0054 (12)	−0.0115 (12)
C10B	0.0473 (15)	0.087 (2)	0.0632 (17)	−0.0144 (15)	0.0069 (12)	0.0109 (17)
C2A	0.0508 (15)	0.094 (3)	0.0736 (19)	0.0098 (16)	−0.0006 (13)	0.002 (2)
C7B	0.0561 (16)	0.075 (2)	0.0647 (17)	0.0071 (15)	0.0077 (13)	−0.0119 (17)
C4A	0.0688 (18)	0.092 (3)	0.0518 (14)	−0.0020 (18)	0.0033 (12)	−0.0188 (18)
C6A	0.094 (2)	0.086 (3)	0.0620 (16)	0.011 (2)	0.0306 (16)	−0.006 (2)
C9B	0.077 (2)	0.086 (3)	0.077 (2)	−0.018 (2)	−0.0017 (18)	0.026 (2)
C10A	0.127 (4)	0.063 (2)	0.064 (2)	0.019 (2)	0.008 (2)	−0.0088 (17)
C8A	0.093 (4)	0.196 (7)	0.121 (4)	0.063 (4)	−0.008 (3)	−0.095 (5)
C9A	0.157 (5)	0.112 (4)	0.090 (3)	0.081 (4)	−0.022 (4)	−0.032 (3)
C8B	0.0590 (17)	0.071 (2)	0.082 (2)	−0.0021 (16)	−0.0105 (15)	−0.0031 (19)
C7A	0.101 (3)	0.141 (5)	0.125 (4)	0.003 (4)	0.058 (3)	−0.048 (4)
N1	0.0451 (11)	0.0539 (14)	0.0544 (11)	−0.0113 (10)	0.0092 (8)	0.0035 (11)

S1—O2	1.407 (2)	C2B—H22B	0.9700
S1—O1	1.416 (2)	C2B—H21B	0.9700
S1—N2B	1.642 (2)	C6B—C7B	1.378 (5)
S1—N1	1.642 (2)	C6B—H6B	0.9300
N2B—C1B	1.389 (4)	C5A—C10A	1.377 (5)
N2B—C3B	1.473 (3)	C5A—C6A	1.380 (5)
C5B—C10B	1.377 (4)	C5A—C4A	1.503 (5)
C5B—C6B	1.392 (4)	C10B—C9B	1.410 (6)
C5B—C4B	1.501 (4)	C10B—H10B	0.9300
O1B—C1B	1.343 (4)	C2A—H21A	0.9700
O1B—C2B	1.444 (4)	C2A—H22A	0.9700
O2A—C1A	1.192 (4)	C7B—C8B	1.339 (6)
O1A—C1A	1.345 (4)	C7B—H7B	0.9300
O1A—C2A	1.453 (5)	C4A—H41A	0.9700
O2B—C1B	1.184 (4)	C4A—H42A	0.9700
O3—C1	1.207 (3)	C6A—C7A	1.372 (7)
N1A—C1	1.385 (3)	C6A—H6A	0.9300
N1A—C1A	1.392 (4)	C9B—C8B	1.360 (6)
N1A—C3A	1.470 (4)	C9B—H9B	0.9300
C4B—C3B	1.531 (4)	C10A—C9A	1.384 (9)
C4B—H42B	0.9700	C10A—H10A	0.9300
C4B—H41B	0.9700	C8A—C7A	1.332 (12)
C1—N1	1.377 (4)	C8A—C9A	1.350 (11)
C3B—C2B	1.526 (4)	C8A—H8A	0.9300
C3B—H3B	0.9800	C9A—H9A	0.9300
C3A—C2A	1.517 (4)	C8B—H8B	0.9300
C3A—C4A	1.521 (5)	C7A—H7A	0.9300
C3A—H3A	0.9800	N1—H1N	0.8600
O2—S1—O1	120.50 (16)	O1A—C1A—N1A	108.3 (3)
O2—S1—N2B	105.02 (12)	O2B—C1B—O1B	123.9 (3)
O1—S1—N2B	110.32 (14)	O2B—C1B—N2B	128.5 (3)
O2—S1—N1	110.68 (14)	O1B—C1B—N2B	107.6 (2)
O1—S1—N1	104.18 (13)	C10A—C5A—C6A	117.6 (4)
N2B—S1—N1	105.28 (12)	C10A—C5A—C4A	123.3 (4)
C1B—N2B—C3B	112.4 (2)	C6A—C5A—C4A	119.1 (3)
C1B—N2B—S1	122.03 (19)	C5B—C10B—C9B	120.7 (3)
C3B—N2B—S1	124.24 (18)	C5B—C10B—H10B	119.7
C10B—C5B—C6B	116.4 (3)	C9B—C10B—H10B	119.7
C10B—C5B—C4B	122.5 (3)	O1A—C2A—C3A	104.0 (3)
C6B—C5B—C4B	121.1 (3)	O1A—C2A—H21A	110.9
C1B—O1B—C2B	110.1 (2)	C3A—C2A—H21A	110.9
C1A—O1A—C2A	109.2 (2)	O1A—C2A—H22A	110.9
C1—N1A—C1A	125.4 (2)	C3A—C2A—H22A	110.9
C1—N1A—C3A	122.7 (2)	H21A—C2A—H22A	109.0
C1A—N1A—C3A	110.7 (2)	C8B—C7B—C6B	120.0 (3)
C5B—C4B—C3B	115.0 (2)	C8B—C7B—H7B	120.0
C5B—C4B—H42B	108.5	C6B—C7B—H7B	120.0
C3B—C4B—H42B	108.5	C5A—C4A—C3A	115.7 (2)
C5B—C4B—H41B	108.5	C5A—C4A—H41A	108.3
C3B—C4B—H41B	108.5	C3A—C4A—H41A	108.3
H42B—C4B—H41B	107.5	C5A—C4A—H42A	108.3
O3—C1—N1	123.8 (2)	C3A—C4A—H42A	108.3
O3—C1—N1A	122.1 (2)	H41A—C4A—H42A	107.4
N1—C1—N1A	114.0 (2)	C7A—C6A—C5A	120.5 (5)
N2B—C3B—C2B	98.7 (2)	C7A—C6A—H6A	119.7
N2B—C3B—C4B	111.6 (2)	C5A—C6A—H6A	119.7
C2B—C3B—C4B	115.1 (2)	C8B—C9B—C10B	120.1 (4)
N2B—C3B—H3B	110.3	C8B—C9B—H9B	119.9
C2B—C3B—H3B	110.3	C10B—C9B—H9B	119.9
C4B—C3B—H3B	110.3	C5A—C10A—C9A	120.3 (5)
N1A—C3A—C2A	99.5 (3)	C5A—C10A—H10A	119.9
N1A—C3A—C4A	112.1 (3)	C9A—C10A—H10A	119.9
C2A—C3A—C4A	111.5 (3)	C7A—C8A—C9A	119.7 (5)
N1A—C3A—H3A	111.1	C7A—C8A—H8A	120.1
C2A—C3A—H3A	111.1	C9A—C8A—H8A	120.1
C4A—C3A—H3A	111.1	C8A—C9A—C10A	120.6 (5)
O1B—C2B—C3B	105.3 (2)	C8A—C9A—H9A	119.7
O1B—C2B—H22B	110.7	C10A—C9A—H9A	119.7
C3B—C2B—H22B	110.7	C7B—C8B—C9B	120.3 (4)
O1B—C2B—H21B	110.7	C7B—C8B—H8B	119.8
C3B—C2B—H21B	110.7	C9B—C8B—H8B	119.8
H22B—C2B—H21B	108.8	C8A—C7A—C6A	121.3 (6)
C7B—C6B—C5B	122.5 (3)	C8A—C7A—H7A	119.4
C7B—C6B—H6B	118.8	C6A—C7A—H7A	119.4
C5B—C6B—H6B	118.8	C1—N1—S1	122.56 (18)
O2A—C1A—O1A	123.1 (3)	C1—N1—H1N	118.7
O2A—C1A—N1A	128.5 (3)	S1—N1—H1N	118.7
O2—S1—N2B—C1B	−177.2 (2)	C2B—O1B—C1B—O2B	168.8 (3)
O1—S1—N2B—C1B	51.6 (2)	C2B—O1B—C1B—N2B	−12.0 (3)
N1—S1—N2B—C1B	−60.3 (2)	C3B—N2B—C1B—O2B	174.7 (3)
O2—S1—N2B—C3B	−11.1 (2)	S1—N2B—C1B—O2B	−17.8 (4)
O1—S1—N2B—C3B	−142.4 (2)	C3B—N2B—C1B—O1B	−4.4 (3)
N1—S1—N2B—C3B	105.8 (2)	S1—N2B—C1B—O1B	163.15 (18)
C10B—C5B—C4B—C3B	−90.1 (3)	C6B—C5B—C10B—C9B	−1.4 (4)
C6B—C5B—C4B—C3B	87.5 (3)	C4B—C5B—C10B—C9B	176.3 (3)
C1A—N1A—C1—O3	−161.7 (3)	C1A—O1A—C2A—C3A	26.0 (4)
C3A—N1A—C1—O3	4.4 (4)	N1A—C3A—C2A—O1A	−27.6 (3)
C1A—N1A—C1—N1	19.6 (4)	C4A—C3A—C2A—O1A	90.8 (3)
C3A—N1A—C1—N1	−174.3 (3)	C5B—C6B—C7B—C8B	0.8 (5)
C1B—N2B—C3B—C2B	17.2 (3)	C10A—C5A—C4A—C3A	83.9 (5)
S1—N2B—C3B—C2B	−149.98 (19)	C6A—C5A—C4A—C3A	−95.7 (4)
C1B—N2B—C3B—C4B	−104.3 (3)	N1A—C3A—C4A—C5A	−67.1 (4)
S1—N2B—C3B—C4B	88.5 (2)	C2A—C3A—C4A—C5A	−177.6 (3)
C5B—C4B—C3B—N2B	61.6 (3)	C10A—C5A—C6A—C7A	−1.1 (6)
C5B—C4B—C3B—C2B	−49.9 (3)	C4A—C5A—C6A—C7A	178.5 (4)
C1—N1A—C3A—C2A	−146.0 (3)	C5B—C10B—C9B—C8B	0.8 (6)
C1A—N1A—C3A—C2A	21.9 (3)	C6A—C5A—C10A—C9A	1.2 (6)
C1—N1A—C3A—C4A	96.0 (3)	C4A—C5A—C10A—C9A	−178.4 (4)
C1A—N1A—C3A—C4A	−96.0 (3)	C7A—C8A—C9A—C10A	0.5 (9)
C1B—O1B—C2B—C3B	23.0 (3)	C5A—C10A—C9A—C8A	−0.9 (7)
N2B—C3B—C2B—O1B	−22.9 (3)	C6B—C7B—C8B—C9B	−1.5 (5)
C4B—C3B—C2B—O1B	96.0 (3)	C10B—C9B—C8B—C7B	0.7 (6)
C10B—C5B—C6B—C7B	0.7 (4)	C9A—C8A—C7A—C6A	−0.4 (9)
C4B—C5B—C6B—C7B	−177.1 (3)	C5A—C6A—C7A—C8A	0.7 (8)
C2A—O1A—C1A—O2A	169.2 (3)	O3—C1—N1—S1	12.8 (4)
C2A—O1A—C1A—N1A	−12.2 (3)	N1A—C1—N1—S1	−168.52 (19)
C1—N1A—C1A—O2A	−21.2 (5)	O2—S1—N1—C1	55.7 (3)
C3A—N1A—C1A—O2A	171.2 (3)	O1—S1—N1—C1	−173.4 (2)
C1—N1A—C1A—O1A	160.3 (3)	N2B—S1—N1—C1	−57.3 (3)
C3A—N1A—C1A—O1A	−7.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2A	0.86	2.07	2.691 (3)	128 (1)
C3B—H3B···O2Ai	0.98	2.58	3.372 (4)	138 (1)
C4B—H42B···O1Bii	0.97	2.48	3.428 (4)	165 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2A	0.86	2.07	2.691 (3)	128 (1)
C3B—H3B⋯O2Ai	0.98	2.58	3.372 (4)	138 (1)
C4B—H42B⋯O1Bii	0.97	2.48	3.428 (4)	165 (1)

Symmetry codes: (i) ; (ii) .