1-(Morpholin-4-yl)-4-(2-nitro-phen-yl)spiro-[azetidine-3,9'-xanthen]-2-one.

In the title compound, C22H21N3O5, the β-lactam (azetidin-2-one) ring is nearly planar [maximum deviation = 0.010 (1) Å] and makes dihedral angles of 69.22 (5), 55.32 (5) and 89.42 (4)° with the least-squares planes formed by the four C atoms of the morpholine ring, which adopts a chair conformation, the benzene ring and the xanthene ring system, respectively. In the crystal, C-H⋯O hydrogen-bond contacts connect neighbouring mol-ecules into infinite zigzag chains running parallel to the b axis.

Related literature

For general background to β-lactams, see: Arya et al. (2014 ▶); Ebrahimi & Jarrahpour (2014 ▶); Singh & Sudheesh (2014 ▶); Zeng et al. (2014 ▶); Zarei et al. (2013 ▶); Jarrahpour & Ebrahimi (2010 ▶); Mehta et al. (2010 ▶); Singh et al. (2011 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶); Nardelli (1995 ▶). For similar structures, see: Akkurt et al. (2008a ▶,b ▶); Yalçın et al. (2009 ▶); Çelik et al. (2009a ▶,b ▶, 2014 ▶).

Experimental

Crystal data

C25H21N3O5

M = 443.45

Monoclinic,

a = 9.4272 (5) Å

b = 18.8525 (8) Å

c = 12.4345 (6) Å

β = 95.443 (4)°

V = 2199.97 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.50 × 0.44 × 0.40 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.956, T max = 0.974

13801 measured reflections

5223 independent reflections

3421 reflections with I > 2σ(I)

R int = 0.195

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.098

S = 1.00

5223 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 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: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814013464/sj5411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013464/sj5411Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013464/sj5411Isup3.cml

CCDC reference: 1007508

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

C25H21N3O5	F(000) = 928
Mr = 443.45	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14473 reflections
a = 9.4272 (5) Å	θ = 1.6–28.4°
b = 18.8525 (8) Å	µ = 0.10 mm−1
c = 12.4345 (6) Å	T = 296 K
β = 95.443 (4)°	Block, light yellow
V = 2199.97 (18) Å3	0.50 × 0.44 × 0.40 mm
Z = 4

Stoe IPDS 2 diffractometer	5223 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3421 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.195
Detector resolution: 6.67 pixels mm-1	θmax = 27.9°, θmin = 2.0°
ω scans	h = −12→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
Tmin = 0.956, Tmax = 0.974	l = −16→16
13801 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0511P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
5223 reflections	Δρmax = 0.15 e Å−3
299 parameters	Δρmin = −0.11 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
O1	0.56523 (11)	0.77674 (4)	0.39775 (8)	0.0607 (3)
O2	0.88039 (12)	0.56659 (6)	0.40826 (8)	0.0725 (4)
O3	0.59829 (13)	0.48451 (5)	0.40169 (9)	0.0738 (4)
O4	0.6611 (2)	0.42173 (8)	0.27221 (13)	0.1293 (7)
O5	0.05898 (13)	0.80037 (7)	0.43054 (10)	0.0862 (5)
N1	0.40654 (11)	0.68165 (5)	0.36241 (8)	0.0475 (3)
N2	0.26494 (11)	0.70325 (5)	0.37024 (8)	0.0504 (3)
N3	0.58819 (15)	0.46781 (6)	0.30725 (11)	0.0673 (5)
C1	0.53326 (14)	0.71537 (6)	0.38183 (9)	0.0459 (4)
C2	0.61723 (13)	0.64499 (6)	0.38092 (9)	0.0439 (4)
C3	0.46359 (13)	0.60880 (6)	0.36101 (9)	0.0444 (4)
C4	0.71522 (13)	0.63736 (6)	0.29281 (9)	0.0450 (4)
C5	0.68634 (14)	0.66829 (7)	0.19146 (10)	0.0527 (4)
C6	0.77624 (16)	0.65986 (8)	0.11144 (11)	0.0610 (5)
C7	0.89724 (16)	0.61957 (8)	0.13129 (12)	0.0648 (5)
C8	0.92974 (16)	0.58875 (8)	0.23033 (12)	0.0665 (5)
C9	0.83854 (14)	0.59821 (7)	0.31040 (10)	0.0536 (4)
C10	0.81733 (15)	0.58925 (7)	0.49807 (10)	0.0554 (4)
C11	0.88545 (17)	0.56948 (9)	0.59700 (12)	0.0697 (6)
C12	0.83068 (17)	0.59109 (8)	0.68992 (12)	0.0668 (5)
C13	0.71169 (18)	0.63341 (7)	0.68493 (11)	0.0631 (5)
C14	0.64380 (16)	0.65115 (7)	0.58589 (10)	0.0555 (4)
C15	0.69405 (14)	0.62872 (6)	0.48998 (10)	0.0465 (4)
C16	0.42467 (13)	0.56881 (6)	0.25733 (10)	0.0477 (4)
C17	0.48294 (15)	0.50353 (6)	0.23145 (10)	0.0536 (4)
C18	0.44357 (19)	0.46854 (8)	0.13552 (12)	0.0691 (6)
C19	0.34418 (19)	0.49821 (9)	0.06166 (12)	0.0749 (6)
C20	0.28575 (18)	0.56245 (10)	0.08314 (12)	0.0736 (6)
C21	0.32615 (15)	0.59701 (8)	0.17932 (11)	0.0605 (5)
C22	0.23610 (17)	0.71132 (8)	0.48318 (11)	0.0640 (5)
C23	0.08391 (19)	0.73546 (10)	0.48559 (15)	0.0822 (7)
C24	0.0851 (2)	0.79149 (11)	0.32138 (15)	0.0905 (7)
C25	0.23701 (19)	0.77036 (8)	0.31261 (12)	0.0712 (6)
H3	0.44030	0.58160	0.42410	0.0530*
H5	0.60420	0.69530	0.17750	0.0630*
H6	0.75520	0.68130	0.04450	0.0730*
H7	0.95760	0.61320	0.07710	0.0780*
H8	1.01210	0.56180	0.24380	0.0800*
H11	0.96750	0.54180	0.60040	0.0840*
H12	0.87440	0.57700	0.75670	0.0800*
H13	0.67740	0.64990	0.74800	0.0760*
H14	0.56200	0.67890	0.58290	0.0670*
H18	0.48450	0.42510	0.12130	0.0830*
H19	0.31650	0.47480	−0.00280	0.0900*
H20	0.21860	0.58300	0.03290	0.0880*
H21	0.28560	0.64080	0.19200	0.0730*
H22A	0.30050	0.74600	0.51880	0.0770*
H22B	0.25040	0.66650	0.52080	0.0770*
H23A	0.02040	0.69950	0.45230	0.0990*
H23B	0.06300	0.74100	0.56000	0.0990*
H24A	0.06510	0.83550	0.28260	0.1090*
H24B	0.02210	0.75530	0.28850	0.1090*
H25A	0.25350	0.76480	0.23730	0.0850*
H25B	0.30070	0.80690	0.34390	0.0850*

	U11	U22	U33	U12	U13	U23
O1	0.0664 (6)	0.0398 (4)	0.0748 (6)	−0.0032 (4)	0.0010 (5)	−0.0022 (4)
O2	0.0706 (7)	0.0878 (7)	0.0609 (6)	0.0346 (6)	0.0163 (5)	0.0220 (5)
O3	0.0973 (9)	0.0551 (6)	0.0684 (6)	0.0094 (5)	0.0043 (6)	0.0026 (5)
O4	0.1586 (16)	0.1034 (10)	0.1227 (11)	0.0737 (10)	−0.0035 (10)	−0.0381 (8)
O5	0.0755 (8)	0.0936 (8)	0.0909 (8)	0.0321 (6)	0.0160 (6)	−0.0121 (7)
N1	0.0447 (6)	0.0409 (5)	0.0574 (6)	0.0033 (4)	0.0068 (4)	−0.0024 (4)
N2	0.0436 (6)	0.0549 (6)	0.0531 (6)	0.0091 (5)	0.0072 (4)	−0.0030 (5)
N3	0.0818 (9)	0.0435 (6)	0.0781 (9)	0.0063 (6)	0.0150 (7)	−0.0064 (6)
C1	0.0496 (7)	0.0411 (6)	0.0469 (6)	−0.0007 (5)	0.0039 (5)	0.0007 (5)
C2	0.0447 (7)	0.0385 (6)	0.0487 (6)	−0.0007 (5)	0.0057 (5)	0.0010 (5)
C3	0.0455 (7)	0.0391 (6)	0.0496 (6)	0.0004 (5)	0.0093 (5)	−0.0006 (5)
C4	0.0441 (7)	0.0401 (6)	0.0512 (7)	−0.0027 (5)	0.0061 (5)	0.0021 (5)
C5	0.0507 (8)	0.0522 (7)	0.0549 (7)	0.0017 (6)	0.0033 (6)	0.0068 (6)
C6	0.0670 (10)	0.0655 (8)	0.0514 (7)	−0.0037 (7)	0.0104 (7)	0.0098 (6)
C7	0.0629 (9)	0.0732 (9)	0.0613 (8)	0.0010 (7)	0.0224 (7)	0.0042 (7)
C8	0.0559 (9)	0.0780 (9)	0.0680 (9)	0.0149 (7)	0.0182 (7)	0.0120 (7)
C9	0.0512 (8)	0.0549 (7)	0.0557 (7)	0.0056 (6)	0.0097 (6)	0.0095 (6)
C10	0.0553 (8)	0.0580 (7)	0.0533 (7)	0.0044 (6)	0.0079 (6)	0.0104 (6)
C11	0.0618 (10)	0.0788 (10)	0.0678 (9)	0.0127 (7)	0.0022 (7)	0.0209 (8)
C12	0.0745 (11)	0.0693 (9)	0.0543 (8)	−0.0103 (8)	−0.0062 (7)	0.0119 (7)
C13	0.0820 (11)	0.0556 (8)	0.0514 (8)	−0.0096 (7)	0.0054 (7)	−0.0032 (6)
C14	0.0644 (9)	0.0490 (7)	0.0530 (7)	−0.0001 (6)	0.0047 (6)	−0.0043 (6)
C15	0.0483 (7)	0.0411 (6)	0.0498 (7)	−0.0037 (5)	0.0036 (5)	0.0022 (5)
C16	0.0472 (7)	0.0465 (6)	0.0511 (7)	−0.0076 (5)	0.0138 (5)	−0.0034 (5)
C17	0.0606 (8)	0.0454 (6)	0.0569 (7)	−0.0063 (6)	0.0170 (6)	−0.0046 (6)
C18	0.0864 (12)	0.0576 (8)	0.0669 (9)	−0.0111 (8)	0.0263 (8)	−0.0158 (7)
C19	0.0825 (12)	0.0869 (11)	0.0567 (9)	−0.0200 (9)	0.0140 (8)	−0.0232 (8)
C20	0.0652 (10)	0.0960 (12)	0.0588 (9)	−0.0075 (8)	0.0017 (7)	−0.0118 (8)
C21	0.0547 (9)	0.0666 (8)	0.0597 (8)	−0.0003 (6)	0.0029 (6)	−0.0091 (7)
C22	0.0656 (9)	0.0724 (9)	0.0555 (8)	0.0085 (7)	0.0137 (7)	0.0006 (7)
C23	0.0694 (11)	0.1011 (13)	0.0805 (11)	0.0075 (9)	0.0295 (9)	−0.0102 (10)
C24	0.0804 (13)	0.1075 (14)	0.0826 (11)	0.0427 (10)	0.0030 (9)	0.0028 (10)
C25	0.0759 (11)	0.0749 (10)	0.0639 (9)	0.0288 (8)	0.0119 (7)	0.0130 (7)

O1—C1	1.2072 (14)	C16—C17	1.3977 (17)
O2—C9	1.3786 (16)	C16—C21	1.3839 (19)
O2—C10	1.3817 (17)	C17—C18	1.3827 (19)
O3—N3	1.2108 (17)	C18—C19	1.368 (2)
O4—N3	1.214 (2)	C19—C20	1.367 (3)
O5—C23	1.411 (2)	C20—C21	1.383 (2)
O5—C24	1.412 (2)	C22—C23	1.508 (2)
N1—N2	1.4078 (15)	C24—C25	1.500 (3)
N1—C1	1.3546 (16)	C3—H3	0.9800
N1—C3	1.4757 (15)	C5—H5	0.9300
N2—C22	1.4635 (17)	C6—H6	0.9300
N2—C25	1.4655 (18)	C7—H7	0.9300
N3—C17	1.4659 (19)	C8—H8	0.9300
C1—C2	1.5456 (17)	C11—H11	0.9300
C2—C3	1.5989 (17)	C12—H12	0.9300
C2—C4	1.5055 (17)	C13—H13	0.9300
C2—C15	1.5071 (17)	C14—H14	0.9300
C3—C16	1.5084 (17)	C18—H18	0.9300
C4—C5	1.3919 (17)	C19—H19	0.9300
C4—C9	1.3769 (18)	C20—H20	0.9300
C5—C6	1.3761 (19)	C21—H21	0.9300
C6—C7	1.373 (2)	C22—H22A	0.9700
C7—C8	1.370 (2)	C22—H22B	0.9700
C8—C9	1.387 (2)	C23—H23A	0.9700
C10—C11	1.384 (2)	C23—H23B	0.9700
C10—C15	1.3756 (19)	C24—H24A	0.9700
C11—C12	1.371 (2)	C24—H24B	0.9700
C12—C13	1.373 (2)	C25—H25A	0.9700
C13—C14	1.3743 (19)	C25—H25B	0.9700
C14—C15	1.3902 (18)
C9—O2—C10	118.08 (11)	C16—C21—C20	122.45 (14)
C23—O5—C24	109.10 (14)	N2—C22—C23	108.31 (12)
N2—N1—C1	132.68 (10)	O5—C23—C22	111.54 (14)
N2—N1—C3	128.25 (9)	O5—C24—C25	110.85 (14)
C1—N1—C3	97.05 (9)	N2—C25—C24	108.79 (14)
N1—N2—C22	111.11 (10)	N1—C3—H3	112.00
N1—N2—C25	110.09 (10)	C2—C3—H3	112.00
C22—N2—C25	109.78 (10)	C16—C3—H3	112.00
O3—N3—O4	122.62 (15)	C4—C5—H5	119.00
O3—N3—C17	119.36 (12)	C6—C5—H5	119.00
O4—N3—C17	118.02 (14)	C5—C6—H6	120.00
O1—C1—N1	132.94 (12)	C7—C6—H6	120.00
O1—C1—C2	134.74 (12)	C6—C7—H7	120.00
N1—C1—C2	92.26 (9)	C8—C7—H7	120.00
C1—C2—C3	84.86 (9)	C7—C8—H8	120.00
C1—C2—C4	115.94 (9)	C9—C8—H8	120.00
C1—C2—C15	111.77 (9)	C10—C11—H11	120.00
C3—C2—C4	117.12 (9)	C12—C11—H11	120.00
C3—C2—C15	113.79 (9)	C11—C12—H12	120.00
C4—C2—C15	111.09 (10)	C13—C12—H12	120.00
N1—C3—C2	85.81 (8)	C12—C13—H13	120.00
N1—C3—C16	114.57 (9)	C14—C13—H13	120.00
C2—C3—C16	119.27 (10)	C13—C14—H14	119.00
C2—C4—C5	122.55 (11)	C15—C14—H14	119.00
C2—C4—C9	120.18 (10)	C17—C18—H18	120.00
C5—C4—C9	117.26 (11)	C19—C18—H18	120.00
C4—C5—C6	121.69 (12)	C18—C19—H19	120.00
C5—C6—C7	119.47 (13)	C20—C19—H19	120.00
C6—C7—C8	120.49 (14)	C19—C20—H20	120.00
C7—C8—C9	119.32 (14)	C21—C20—H20	120.00
O2—C9—C4	122.59 (11)	C16—C21—H21	119.00
O2—C9—C8	115.65 (12)	C20—C21—H21	119.00
C4—C9—C8	121.76 (12)	N2—C22—H22A	110.00
O2—C10—C11	115.87 (13)	N2—C22—H22B	110.00
O2—C10—C15	122.24 (11)	C23—C22—H22A	110.00
C11—C10—C15	121.89 (13)	C23—C22—H22B	110.00
C10—C11—C12	119.27 (15)	H22A—C22—H22B	108.00
C11—C12—C13	120.38 (14)	O5—C23—H23A	109.00
C12—C13—C14	119.40 (13)	O5—C23—H23B	109.00
C13—C14—C15	121.81 (13)	C22—C23—H23A	109.00
C2—C15—C10	120.43 (11)	C22—C23—H23B	109.00
C2—C15—C14	122.43 (12)	H23A—C23—H23B	108.00
C10—C15—C14	117.13 (12)	O5—C24—H24A	109.00
C3—C16—C17	124.60 (11)	O5—C24—H24B	109.00
C3—C16—C21	119.98 (11)	C25—C24—H24A	109.00
C17—C16—C21	115.42 (12)	C25—C24—H24B	109.00
N3—C17—C16	120.88 (11)	H24A—C24—H24B	108.00
N3—C17—C18	116.45 (12)	N2—C25—H25A	110.00
C16—C17—C18	122.65 (13)	N2—C25—H25B	110.00
C17—C18—C19	119.66 (14)	C24—C25—H25A	110.00
C18—C19—C20	119.61 (14)	C24—C25—H25B	110.00
C19—C20—C21	120.21 (15)	H25A—C25—H25B	108.00
C9—O2—C10—C11	−164.66 (13)	C15—C2—C3—C16	−131.34 (11)
C9—O2—C10—C15	15.67 (19)	C15—C2—C4—C5	−160.75 (11)
C10—O2—C9—C4	−16.61 (19)	C1—C2—C4—C9	148.72 (11)
C10—O2—C9—C8	162.73 (13)	C15—C2—C4—C9	19.71 (15)
C23—O5—C24—C25	−61.03 (18)	C15—C2—C3—N1	112.75 (10)
C24—O5—C23—C22	60.87 (18)	C2—C3—C16—C17	70.79 (16)
N2—N1—C1—O1	−11.8 (2)	C2—C3—C16—C21	−108.37 (14)
C3—N1—N2—C25	−149.25 (11)	N1—C3—C16—C21	−8.93 (17)
C1—N1—N2—C22	−71.02 (15)	N1—C3—C16—C17	170.23 (11)
C3—N1—N2—C22	88.92 (13)	C5—C4—C9—C8	−1.01 (19)
N2—N1—C3—C2	−166.66 (11)	C2—C4—C5—C6	−179.05 (12)
C1—N1—C3—C2	−1.38 (9)	C2—C4—C9—C8	178.56 (12)
N2—N1—C3—C16	72.97 (14)	C5—C4—C9—O2	178.30 (12)
C3—N1—C1—O1	−176.04 (14)	C2—C4—C9—O2	−2.14 (19)
N2—N1—C1—C2	165.68 (11)	C9—C4—C5—C6	0.51 (19)
C1—N1—N2—C25	50.80 (16)	C4—C5—C6—C7	0.5 (2)
C3—N1—C1—C2	1.42 (9)	C5—C6—C7—C8	−0.9 (2)
C1—N1—C3—C16	−121.74 (11)	C6—C7—C8—C9	0.5 (2)
C22—N2—C25—C24	−58.02 (15)	C7—C8—C9—C4	0.6 (2)
N1—N2—C22—C23	179.19 (11)	C7—C8—C9—O2	−178.80 (13)
C25—N2—C22—C23	57.18 (16)	C11—C10—C15—C14	3.1 (2)
N1—N2—C25—C24	179.37 (12)	O2—C10—C11—C12	178.81 (14)
O3—N3—C17—C18	−159.81 (14)	O2—C10—C15—C14	−177.26 (12)
O4—N3—C17—C16	−161.84 (14)	C11—C10—C15—C2	−175.75 (13)
O3—N3—C17—C16	18.9 (2)	O2—C10—C15—C2	3.91 (19)
O4—N3—C17—C18	19.4 (2)	C15—C10—C11—C12	−1.5 (2)
N1—C1—C2—C4	116.42 (11)	C10—C11—C12—C13	−1.7 (2)
N1—C1—C2—C15	−114.90 (10)	C11—C12—C13—C14	3.1 (2)
O1—C1—C2—C3	176.08 (14)	C12—C13—C14—C15	−1.5 (2)
N1—C1—C2—C3	−1.31 (8)	C13—C14—C15—C2	177.22 (12)
O1—C1—C2—C4	−66.19 (18)	C13—C14—C15—C10	−1.6 (2)
O1—C1—C2—C15	62.49 (18)	C3—C16—C17—C18	179.68 (13)
C1—C2—C3—N1	1.20 (8)	C17—C16—C21—C20	1.2 (2)
C4—C2—C3—N1	−115.37 (10)	C21—C16—C17—N3	−179.79 (12)
C1—C2—C3—C16	117.11 (10)	C3—C16—C17—N3	1.0 (2)
C4—C2—C3—C16	0.54 (15)	C21—C16—C17—C18	−1.1 (2)
C1—C2—C4—C5	−31.73 (16)	C3—C16—C21—C20	−179.54 (13)
C4—C2—C15—C10	−20.60 (16)	N3—C17—C18—C19	178.99 (14)
C4—C2—C15—C14	160.64 (11)	C16—C17—C18—C19	0.3 (2)
C3—C2—C4—C9	−113.39 (13)	C17—C18—C19—C20	0.6 (3)
C3—C2—C4—C5	66.16 (15)	C18—C19—C20—C21	−0.5 (3)
C1—C2—C15—C10	−151.80 (12)	C19—C20—C21—C16	−0.5 (2)
C1—C2—C15—C14	29.43 (16)	N2—C22—C23—O5	−59.13 (17)
C3—C2—C15—C10	114.15 (13)	O5—C24—C25—N2	59.98 (18)
C3—C2—C15—C14	−64.62 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.98	2.55	3.5310 (16)	174
C6—H6···O1ii	0.93	2.56	3.3828 (17)	148
C11—H11···O2iii	0.93	2.50	3.389 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.98	2.55	3.5310 (16)	174
C6—H6⋯O1ii	0.93	2.56	3.3828 (17)	148
C11—H11⋯O2iii	0.93	2.50	3.389 (2)	159

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