9α-Hy-droxy-12-{[4-(4-hy-droxy-phen-yl)piperazin-1-yl]meth-yl}-4,8-dimethyl-3,14-dioxatri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one.

The title compound, C25H34N2O5, was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which in turn was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule comprises a ten-membered ring fused to a five-membered ring with an additional ep-oxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hy-droxy-phenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy-droxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intra-molecular O-H⋯N hydrogen-bond stabilizes the mol-ecular conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the a-axis direction.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996 ▶); El Hassany et al. (2004 ▶). For the reactivity of this sesquiterpene, see: Hwang et al. (2006 ▶); Neelakantan et al. (2009 ▶). For a related synthetic procedure, see: Moumou et al. (2012 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H34N2O5

M = 442.54

Monoclinic,

a = 29.880 (5) Å

b = 6.841 (5) Å

c = 11.999 (5) Å

β = 102.307 (5)°

V = 2396 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.5 × 0.03 × 0.03 mm

Data collection

Bruker X8 APEX Diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.639, T max = 0.747

13097 measured reflections

2868 independent reflections

1830 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.08

2868 reflections

322 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814007430/sj5394sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007430/sj5394Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007430/sj5394Isup3.cml

CCDC reference: 995311

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

C25H34N2O5	F(000) = 952
Mr = 442.54	Dx = 1.227 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 4801 reflections
a = 29.880 (5) Å	θ = 2.5–27.1°
b = 6.841 (5) Å	µ = 0.09 mm−1
c = 11.999 (5) Å	T = 296 K
β = 102.307 (5)°	Needle, colourless
V = 2396 (2) Å3	0.5 × 0.03 × 0.03 mm
Z = 4

Bruker X8 APEX Diffractometer	2868 independent reflections
Radiation source: fine-focus sealed tube	1830 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 27.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −38→38
Tmin = 0.639, Tmax = 0.747	k = −8→7
13097 measured 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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0408P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2868 reflections	Δρmax = 0.14 e Å−3
322 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (6)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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	Occ. (<1)
C1	0.81526 (10)	0.5109 (5)	0.7206 (2)	0.0388 (7)
H1	0.8380	0.4421	0.7782	0.047*
C2	0.78537 (10)	0.6359 (5)	0.7759 (2)	0.0425 (7)
H2	0.7681	0.7338	0.7245	0.051*
C3	0.79457 (11)	0.6940 (5)	0.8964 (2)	0.0478 (8)
C4	0.77809 (13)	0.8925 (6)	0.9221 (3)	0.0645 (10)
H4A	0.7699	0.8898	0.9961	0.077*
H4B	0.7508	0.9254	0.8655	0.077*
C5	0.81482 (14)	1.0505 (5)	0.9224 (3)	0.0687 (11)
H5A	0.8007	1.1787	0.9185	0.082*
H5B	0.8376	1.0428	0.9931	0.082*
C6	0.83780 (13)	1.0258 (5)	0.8232 (3)	0.0548 (9)
H6	0.8195	1.0503	0.7516	0.066*
C7	0.88024 (13)	0.9743 (5)	0.8241 (3)	0.0544 (9)
C8	0.89540 (12)	0.9174 (5)	0.7157 (3)	0.0545 (9)
H8	0.9283	0.9432	0.7273	0.065*
C9	0.88783 (10)	0.6976 (5)	0.6916 (2)	0.0464 (8)
H9A	0.9070	0.6580	0.6397	0.056*
H9B	0.8985	0.6275	0.7625	0.056*
C10	0.83879 (10)	0.6316 (4)	0.6409 (2)	0.0369 (7)
H10	0.8203	0.7490	0.6184	0.044*
C11	0.83398 (10)	0.5009 (5)	0.5360 (2)	0.0420 (7)
H11	0.8624	0.4278	0.5393	0.050*
C12	0.79599 (11)	0.3623 (5)	0.5444 (2)	0.0452 (8)
C13	0.83375 (13)	0.6105 (6)	0.9824 (2)	0.0674 (11)
H13A	0.8596	0.6970	0.9913	0.101*
H13B	0.8419	0.4852	0.9566	0.101*
H13C	0.8249	0.5957	1.0542	0.101*
C14	0.91847 (14)	0.9532 (7)	0.9290 (3)	0.0855 (13)
H14A	0.9427	1.0427	0.9241	0.128*
H14B	0.9300	0.8218	0.9334	0.128*
H14C	0.9069	0.9817	0.9959	0.128*
C15	0.82137 (11)	0.6135 (5)	0.4222 (2)	0.0498 (8)
H15A	0.8201	0.5223	0.3597	0.060*
H15B	0.7911	0.6702	0.4150	0.060*
C16	0.89578 (11)	0.6953 (5)	0.3813 (3)	0.0574 (9)
H16A	0.8876	0.6275	0.3089	0.069*
H16B	0.9106	0.6023	0.4385	0.069*
C17	0.92853 (12)	0.8583 (6)	0.3722 (3)	0.0620 (10)
H17A	0.9380	0.9213	0.4459	0.074*
H17B	0.9556	0.8049	0.3508	0.074*
C18	0.83255 (11)	0.9076 (5)	0.3240 (3)	0.0559 (9)
H18A	0.8048	0.9589	0.3427	0.067*
H18B	0.8242	0.8397	0.2516	0.067*
C19	0.86433 (12)	1.0737 (5)	0.3134 (3)	0.0585 (10)
H19A	0.8494	1.1610	0.2531	0.070*
H19B	0.8709	1.1471	0.3841	0.070*
C20	0.93639 (12)	1.1478 (5)	0.2585 (3)	0.0524 (8)
C21A	0.9766 (11)	1.167 (5)	0.303 (2)	0.103 (11)	0.47 (5)
H21A	0.9892	1.0838	0.3630	0.124*	0.47 (5)
C22A	1.0052 (11)	1.307 (6)	0.269 (3)	0.184 (19)	0.47 (5)
H22A	1.0353	1.3161	0.3092	0.220*	0.47 (5)
C21B	0.9877 (9)	1.150 (3)	0.3049 (16)	0.059 (4)	0.53 (5)
H21B	1.0010	1.0609	0.3605	0.071*	0.53 (5)
C22B	1.0145 (8)	1.284 (2)	0.2650 (12)	0.066 (5)	0.53 (5)
H22B	1.0462	1.2840	0.2894	0.079*	0.53 (5)
C23	0.99198 (17)	1.4234 (8)	0.1851 (4)	0.0947 (15)
C24	0.94645 (15)	1.4229 (6)	0.1412 (3)	0.0817 (13)
H24	0.9337	1.5159	0.0872	0.098*
C25	0.91882 (13)	1.2851 (6)	0.1763 (3)	0.0616 (10)
H25	0.8876	1.2844	0.1440	0.074*
N1	0.85421 (8)	0.7703 (4)	0.41259 (18)	0.0446 (6)
N2	0.90743 (9)	1.0027 (4)	0.2877 (2)	0.0527 (7)
O1	0.78550 (7)	0.3726 (3)	0.64797 (15)	0.0455 (5)
O2	0.75946 (8)	0.5494 (4)	0.85303 (16)	0.0582 (7)
O3	0.87276 (10)	1.0320 (4)	0.62102 (19)	0.0689 (7)
H3	0.8708	0.9690	0.5620	0.103*
O4	0.77554 (8)	0.2523 (4)	0.47254 (18)	0.0653 (7)
O5A	1.0188 (7)	1.589 (4)	0.174 (3)	0.116 (8)	0.47 (5)
H5A1	1.0053	1.6567	0.1208	0.173*	0.47 (5)
O5B	1.0186 (6)	1.531 (3)	0.1318 (16)	0.080 (4)	0.53 (5)
H5B1	1.0034	1.5704	0.0709	0.120*	0.53 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0456 (18)	0.0352 (17)	0.0330 (13)	−0.0035 (15)	0.0025 (12)	−0.0011 (13)
C2	0.0496 (19)	0.0439 (19)	0.0364 (14)	−0.0019 (15)	0.0147 (13)	0.0051 (13)
C3	0.059 (2)	0.0478 (19)	0.0391 (15)	−0.0061 (18)	0.0159 (15)	−0.0022 (15)
C4	0.075 (2)	0.069 (3)	0.0551 (19)	0.004 (2)	0.0274 (18)	−0.0153 (19)
C5	0.089 (3)	0.044 (2)	0.078 (2)	0.003 (2)	0.028 (2)	−0.0179 (18)
C6	0.080 (3)	0.0266 (18)	0.0600 (19)	0.0035 (18)	0.0194 (18)	−0.0011 (15)
C7	0.068 (2)	0.040 (2)	0.0543 (18)	−0.0102 (19)	0.0107 (17)	−0.0105 (16)
C8	0.061 (2)	0.044 (2)	0.0589 (19)	−0.0102 (18)	0.0134 (16)	−0.0023 (16)
C9	0.051 (2)	0.042 (2)	0.0467 (16)	−0.0034 (16)	0.0113 (14)	−0.0057 (15)
C10	0.0417 (17)	0.0323 (17)	0.0363 (14)	−0.0004 (14)	0.0075 (12)	−0.0029 (12)
C11	0.0441 (18)	0.046 (2)	0.0355 (14)	−0.0034 (16)	0.0082 (12)	−0.0079 (14)
C12	0.050 (2)	0.0412 (19)	0.0432 (16)	0.0006 (17)	0.0074 (14)	−0.0051 (15)
C13	0.091 (3)	0.062 (2)	0.0424 (17)	−0.003 (2)	−0.0015 (17)	−0.0021 (16)
C14	0.084 (3)	0.102 (4)	0.065 (2)	−0.012 (3)	0.003 (2)	−0.029 (2)
C15	0.052 (2)	0.059 (2)	0.0403 (15)	−0.0026 (18)	0.0136 (14)	−0.0042 (15)
C16	0.056 (2)	0.055 (2)	0.068 (2)	0.0122 (19)	0.0284 (17)	0.0078 (18)
C17	0.057 (2)	0.056 (2)	0.079 (2)	0.018 (2)	0.0284 (18)	0.0184 (19)
C18	0.053 (2)	0.065 (2)	0.0532 (18)	0.0101 (19)	0.0180 (16)	0.0112 (17)
C19	0.061 (2)	0.057 (2)	0.0636 (19)	0.0196 (19)	0.0258 (17)	0.0146 (17)
C20	0.051 (2)	0.051 (2)	0.0564 (19)	0.0008 (18)	0.0149 (17)	0.0001 (17)
C21A	0.026 (12)	0.111 (16)	0.168 (17)	0.010 (9)	0.009 (8)	0.088 (13)
C22A	0.034 (10)	0.23 (3)	0.27 (3)	−0.002 (12)	−0.005 (11)	0.13 (3)
C21B	0.025 (9)	0.062 (8)	0.085 (8)	0.017 (6)	0.002 (5)	0.015 (7)
C22B	0.041 (7)	0.049 (8)	0.097 (9)	−0.011 (5)	−0.005 (5)	0.022 (6)
C23	0.072 (3)	0.087 (4)	0.116 (4)	−0.027 (3)	−0.001 (3)	0.033 (3)
C24	0.080 (3)	0.077 (3)	0.079 (2)	−0.025 (3)	−0.003 (2)	0.025 (2)
C25	0.062 (2)	0.058 (2)	0.059 (2)	−0.010 (2)	0.0006 (17)	0.0061 (19)
N1	0.0462 (16)	0.0481 (16)	0.0422 (13)	0.0059 (13)	0.0156 (11)	0.0046 (12)
N2	0.0531 (17)	0.0512 (18)	0.0590 (15)	0.0100 (15)	0.0233 (13)	0.0086 (14)
O1	0.0577 (14)	0.0379 (12)	0.0422 (11)	−0.0094 (11)	0.0136 (9)	−0.0071 (9)
O2	0.0718 (16)	0.0643 (17)	0.0440 (11)	−0.0185 (14)	0.0245 (10)	−0.0059 (11)
O3	0.100 (2)	0.0462 (15)	0.0619 (13)	−0.0122 (15)	0.0210 (14)	0.0062 (12)
O4	0.0738 (17)	0.0670 (17)	0.0549 (13)	−0.0186 (14)	0.0136 (12)	−0.0250 (12)
O5A	0.090 (7)	0.087 (11)	0.138 (16)	−0.065 (8)	−0.048 (9)	0.047 (10)
O5B	0.066 (5)	0.084 (9)	0.080 (6)	−0.054 (5)	−0.010 (5)	0.029 (6)

C1—O1	1.454 (3)	C15—N1	1.475 (4)
C1—C2	1.490 (4)	C15—H15A	0.9700
C1—C10	1.542 (4)	C15—H15B	0.9700
C1—H1	0.9800	C16—N1	1.464 (4)
C2—O2	1.454 (3)	C16—C17	1.503 (5)
C2—C3	1.468 (4)	C16—H16A	0.9700
C2—H2	0.9800	C16—H16B	0.9700
C3—O2	1.455 (4)	C17—N2	1.459 (4)
C3—C13	1.499 (4)	C17—H17A	0.9700
C3—C4	1.499 (5)	C17—H17B	0.9700
C4—C5	1.540 (5)	C18—N1	1.462 (4)
C4—H4A	0.9700	C18—C19	1.504 (5)
C4—H4B	0.9700	C18—H18A	0.9700
C5—C6	1.505 (5)	C18—H18B	0.9700
C5—H5A	0.9700	C19—N2	1.469 (4)
C5—H5B	0.9700	C19—H19A	0.9700
C6—C7	1.314 (5)	C19—H19B	0.9700
C6—H6	0.9300	C20—C21A	1.21 (3)
C7—C14	1.516 (5)	C20—C25	1.381 (5)
C7—C8	1.516 (4)	C20—N2	1.409 (4)
C8—O3	1.426 (4)	C20—C21B	1.52 (3)
C8—C9	1.539 (5)	C21A—C22A	1.41 (4)
C8—H8	0.9800	C21A—H21A	0.9300
C9—C10	1.530 (4)	C22A—C23	1.27 (3)
C9—H9A	0.9700	C22A—H22A	0.9300
C9—H9B	0.9700	C21B—C22B	1.37 (3)
C10—C11	1.526 (4)	C21B—H21B	0.9300
C10—H10	0.9800	C22B—C23	1.415 (18)
C11—C12	1.499 (4)	C22B—H22B	0.9300
C11—C15	1.543 (4)	C23—O5B	1.340 (15)
C11—H11	0.9800	C23—C24	1.350 (6)
C12—O4	1.208 (3)	C23—O5A	1.411 (17)
C12—O1	1.347 (3)	C24—C25	1.377 (5)
C13—H13A	0.9600	C24—H24	0.9300
C13—H13B	0.9600	C25—H25	0.9300
C13—H13C	0.9600	O3—H3	0.8200
C14—H14A	0.9600	O5A—H5A1	0.8200
C14—H14B	0.9600	O5B—H5B1	0.8200
C14—H14C	0.9600
O1—C1—C2	107.0 (2)	N1—C15—C11	113.0 (2)
O1—C1—C10	106.13 (18)	N1—C15—H15A	109.0
C2—C1—C10	111.3 (2)	C11—C15—H15A	109.0
O1—C1—H1	110.7	N1—C15—H15B	109.0
C2—C1—H1	110.7	C11—C15—H15B	109.0
C10—C1—H1	110.7	H15A—C15—H15B	107.8
O2—C2—C3	59.74 (17)	N1—C16—C17	111.1 (3)
O2—C2—C1	120.0 (3)	N1—C16—H16A	109.4
C3—C2—C1	126.1 (3)	C17—C16—H16A	109.4
O2—C2—H2	113.5	N1—C16—H16B	109.4
C3—C2—H2	113.5	C17—C16—H16B	109.4
C1—C2—H2	113.5	H16A—C16—H16B	108.0
O2—C3—C2	59.63 (18)	N2—C17—C16	111.2 (3)
O2—C3—C13	112.6 (3)	N2—C17—H17A	109.4
C2—C3—C13	122.0 (3)	C16—C17—H17A	109.4
O2—C3—C4	116.5 (3)	N2—C17—H17B	109.4
C2—C3—C4	116.6 (3)	C16—C17—H17B	109.4
C13—C3—C4	116.5 (3)	H17A—C17—H17B	108.0
C3—C4—C5	111.8 (3)	N1—C18—C19	111.0 (3)
C3—C4—H4A	109.3	N1—C18—H18A	109.4
C5—C4—H4A	109.3	C19—C18—H18A	109.4
C3—C4—H4B	109.3	N1—C18—H18B	109.4
C5—C4—H4B	109.3	C19—C18—H18B	109.4
H4A—C4—H4B	107.9	H18A—C18—H18B	108.0
C6—C5—C4	111.4 (3)	N2—C19—C18	111.5 (3)
C6—C5—H5A	109.4	N2—C19—H19A	109.3
C4—C5—H5A	109.4	C18—C19—H19A	109.3
C6—C5—H5B	109.4	N2—C19—H19B	109.3
C4—C5—H5B	109.4	C18—C19—H19B	109.3
H5A—C5—H5B	108.0	H19A—C19—H19B	108.0
C7—C6—C5	128.8 (3)	C21A—C20—C25	115.6 (14)
C7—C6—H6	115.6	C21A—C20—N2	124.6 (14)
C5—C6—H6	115.6	C25—C20—N2	119.8 (3)
C6—C7—C14	126.0 (3)	C21A—C20—C21B	7 (2)
C6—C7—C8	121.7 (3)	C25—C20—C21B	117.1 (10)
C14—C7—C8	112.2 (3)	N2—C20—C21B	122.9 (10)
O3—C8—C7	111.4 (3)	C20—C21A—C22A	123 (2)
O3—C8—C9	111.2 (3)	C20—C21A—H21A	118.3
C7—C8—C9	110.7 (3)	C22A—C21A—H21A	118.3
O3—C8—H8	107.8	C23—C22A—C21A	124 (2)
C7—C8—H8	107.8	C23—C22A—H22A	118.2
C9—C8—H8	107.8	C21A—C22A—H22A	118.2
C10—C9—C8	116.9 (3)	C22B—C21B—C20	120.0 (17)
C10—C9—H9A	108.1	C22B—C21B—H21B	120.0
C8—C9—H9A	108.1	C20—C21B—H21B	120.0
C10—C9—H9B	108.1	C21B—C22B—C23	117.2 (17)
C8—C9—H9B	108.1	C21B—C22B—H22B	121.4
H9A—C9—H9B	107.3	C23—C22B—H22B	121.4
C11—C10—C9	114.5 (2)	C22A—C23—O5B	127.0 (17)
C11—C10—C1	102.9 (2)	C22A—C23—C24	115.0 (15)
C9—C10—C1	115.9 (2)	O5B—C23—C24	117.8 (8)
C11—C10—H10	107.7	C22A—C23—O5A	119.3 (17)
C9—C10—H10	107.7	O5B—C23—O5A	26.9 (13)
C1—C10—H10	107.7	C24—C23—O5A	120.6 (10)
C12—C11—C10	104.8 (2)	C22A—C23—C22B	13 (2)
C12—C11—C15	109.2 (2)	O5B—C23—C22B	116.5 (12)
C10—C11—C15	113.6 (3)	C24—C23—C22B	123.9 (9)
C12—C11—H11	109.7	O5A—C23—C22B	114.0 (11)
C10—C11—H11	109.7	C23—C24—C25	120.2 (4)
C15—C11—H11	109.7	C23—C24—H24	119.9
O4—C12—O1	120.6 (3)	C25—C24—H24	119.9
O4—C12—C11	128.4 (3)	C24—C25—C20	121.5 (4)
O1—C12—C11	110.9 (2)	C24—C25—H25	119.3
C3—C13—H13A	109.5	C20—C25—H25	119.3
C3—C13—H13B	109.5	C18—N1—C16	107.9 (2)
H13A—C13—H13B	109.5	C18—N1—C15	109.0 (2)
C3—C13—H13C	109.5	C16—N1—C15	112.3 (3)
H13A—C13—H13C	109.5	C20—N2—C17	116.9 (3)
H13B—C13—H13C	109.5	C20—N2—C19	115.6 (3)
C7—C14—H14A	109.5	C17—N2—C19	110.2 (2)
C7—C14—H14B	109.5	C12—O1—C1	110.8 (2)
H14A—C14—H14B	109.5	C2—O2—C3	60.63 (18)
C7—C14—H14C	109.5	C8—O3—H3	109.5
H14A—C14—H14C	109.5	C23—O5A—H5A1	109.5
H14B—C14—H14C	109.5	C23—O5B—H5B1	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	2.22	3.030 (4)	169
C2—H2···O4i	0.98	2.45	3.243 (4)	138
C4—H4A···O2ii	0.97	2.43	3.315 (5)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	2.22	3.030 (4)	169
C2—H2⋯O4i	0.98	2.45	3.243 (4)	138
C4—H4A⋯O2ii	0.97	2.43	3.315 (5)	151

Symmetry codes: (i) ; (ii) .