Methyl rac-(2R,11S,12R)-12-(2-chloro-phen-yl)-22-oxo-9,13,21-trioxapenta-cyclo-[12.8.0.0.0.0]docosa-1(14),3,5,7,15(20),16,18-hepta-ene-11-carboxyl-ate.

In the title compound C(27)H(19)ClO(6), the coumarin ring system is not exactly planar, with a dihedral angle of 4.12 (7)° between its benzene and lactone rings. The cis-fused pyran rings adopt half-chair conformations. The carbometh-oxy and chloro-phenyl groups are in a trans configuration. The crystal packing is stabilized by inter-molecular C-H⋯O interactions, which produce a centrosymmetric R(2) (2)(14) dimer and two centrosymmetric R(2) (2)(18) dimers connecting the mol-ecules in a two-dimensional fashion.

Related literature

For uses of coumarins, see: Kayser & Kolodziej (1997 ▶); Fan et al. (2001 ▶); Wang et al. (2002 ▶). For related structures, see: Kanchanadevi et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C27H19ClO6

M = 474.87

Triclinic,

a = 8.4441 (3) Å

b = 9.7556 (3) Å

c = 13.8546 (5) Å

α = 73.831 (2)°

β = 82.858 (2)°

γ = 87.962 (2)°

V = 1087.65 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

26685 measured reflections

6336 independent reflections

4968 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.143

S = 1.01

6336 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037196/ld2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037196/ld2025Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037196/ld2025Isup3.cml

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

C27H19ClO6	Z = 2
Mr = 474.87	F(000) = 492
Triclinic, P1	Dx = 1.450 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4441 (3) Å	Cell parameters from 6336 reflections
b = 9.7556 (3) Å	θ = 2.2–30.0°
c = 13.8546 (5) Å	µ = 0.22 mm−1
α = 73.831 (2)°	T = 293 K
β = 82.858 (2)°	Block, colourless
γ = 87.962 (2)°	0.30 × 0.25 × 0.25 mm
V = 1087.65 (6) Å3

Bruker Kappa APEXII CCD diffractometer	4968 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 30.0°, θmin = 2.2°
ω scans	h = −11→11
26685 measured reflections	k = −12→13
6336 independent reflections	l = −19→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0742P)2 + 0.3227P] where P = (Fo2 + 2Fc2)/3
6336 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
C1	0.65779 (17)	0.56358 (17)	0.40142 (11)	0.0427 (3)
H1	0.6784	0.5199	0.4674	0.051*
C2	0.6817 (2)	0.70748 (18)	0.36081 (13)	0.0485 (4)
H2	0.7199	0.7612	0.3989	0.058*
C3	0.6491 (2)	0.77270 (17)	0.26310 (13)	0.0493 (4)
H3	0.6674	0.8699	0.2349	0.059*
C4	0.58945 (19)	0.69331 (15)	0.20757 (11)	0.0424 (3)
H4	0.5632	0.7389	0.1431	0.051*
C5	0.56753 (15)	0.54613 (14)	0.24582 (9)	0.0331 (3)
C6	0.60257 (15)	0.48263 (14)	0.34399 (10)	0.0345 (3)
C7	0.51941 (16)	0.25398 (14)	0.33923 (10)	0.0355 (3)
H7A	0.4668	0.1716	0.3874	0.043*
H7B	0.6078	0.2197	0.3004	0.043*
C8	0.40116 (14)	0.33317 (13)	0.26765 (9)	0.0302 (2)
C9	0.48878 (14)	0.45976 (13)	0.18856 (9)	0.0301 (2)
H9	0.4088	0.5205	0.1515	0.036*
C10	0.59876 (14)	0.40135 (13)	0.11382 (9)	0.0311 (2)
C11	0.58170 (14)	0.26821 (14)	0.10487 (9)	0.0323 (2)
C12	0.33567 (14)	0.23433 (14)	0.21156 (9)	0.0322 (2)
H12	0.2696	0.2912	0.1614	0.039*
C13	0.71735 (16)	0.49406 (15)	0.04264 (9)	0.0369 (3)
C14	0.81399 (16)	0.29644 (16)	−0.01975 (10)	0.0391 (3)
C15	0.68874 (15)	0.21021 (15)	0.03630 (9)	0.0347 (3)
C16	0.67418 (18)	0.07365 (17)	0.02455 (11)	0.0432 (3)
H16	0.5907	0.0146	0.0615	0.052*
C17	0.7832 (2)	0.0264 (2)	−0.04158 (14)	0.0546 (4)
H17	0.7722	−0.0637	−0.0505	0.066*
C18	0.9098 (2)	0.1137 (2)	−0.09498 (14)	0.0590 (4)
H18	0.9841	0.0806	−0.1387	0.071*
C19	0.92701 (19)	0.2478 (2)	−0.08424 (12)	0.0531 (4)
H19	1.0128	0.3051	−0.1195	0.064*
C20	0.23943 (16)	0.10893 (14)	0.27860 (10)	0.0362 (3)
C21	0.3141 (2)	−0.01302 (16)	0.33065 (13)	0.0484 (4)
H21	0.4247	−0.0198	0.3203	0.058*
C22	0.2274 (3)	−0.12563 (19)	0.39802 (15)	0.0646 (5)
H22	0.2798	−0.2062	0.4331	0.078*
C23	0.0635 (3)	−0.1172 (2)	0.41250 (16)	0.0699 (6)
H23	0.0051	−0.1916	0.4584	0.084*
C24	−0.0138 (2)	−0.0002 (2)	0.35981 (15)	0.0619 (5)
H24	−0.1246	0.0045	0.3690	0.074*
C25	0.07359 (17)	0.11175 (18)	0.29258 (12)	0.0454 (3)
C26	0.26076 (15)	0.38165 (15)	0.33110 (10)	0.0352 (3)
C27	0.0578 (3)	0.5498 (3)	0.33678 (18)	0.0788 (7)
H27A	−0.0335	0.4941	0.3363	0.118*
H27B	0.0379	0.6486	0.3049	0.118*
H27C	0.0771	0.5384	0.4054	0.118*
O1	0.57971 (13)	0.34145 (11)	0.39277 (7)	0.0437 (2)
O2	0.46794 (11)	0.17495 (10)	0.15960 (7)	0.0386 (2)
O3	0.82713 (12)	0.43425 (12)	−0.01572 (8)	0.0439 (2)
O4	0.72725 (15)	0.62092 (12)	0.02839 (8)	0.0514 (3)
O5	0.21355 (14)	0.31564 (13)	0.41573 (8)	0.0511 (3)
O6	0.19620 (14)	0.50185 (13)	0.28202 (9)	0.0556 (3)
Cl1	−0.03104 (5)	0.25730 (6)	0.22616 (5)	0.07724 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0385 (7)	0.0535 (8)	0.0382 (7)	−0.0064 (6)	−0.0058 (5)	−0.0149 (6)
C2	0.0478 (8)	0.0524 (9)	0.0516 (8)	−0.0101 (7)	−0.0021 (6)	−0.0251 (7)
C3	0.0576 (9)	0.0389 (7)	0.0524 (9)	−0.0087 (6)	0.0015 (7)	−0.0165 (6)
C4	0.0510 (8)	0.0350 (7)	0.0385 (7)	−0.0050 (6)	−0.0011 (6)	−0.0068 (5)
C5	0.0313 (6)	0.0350 (6)	0.0319 (6)	−0.0047 (5)	−0.0005 (4)	−0.0081 (5)
C6	0.0290 (5)	0.0388 (6)	0.0342 (6)	−0.0039 (5)	−0.0029 (4)	−0.0076 (5)
C7	0.0352 (6)	0.0341 (6)	0.0331 (6)	−0.0027 (5)	−0.0057 (5)	−0.0017 (5)
C8	0.0277 (5)	0.0324 (6)	0.0271 (5)	−0.0046 (4)	−0.0006 (4)	−0.0034 (4)
C9	0.0291 (5)	0.0307 (5)	0.0274 (5)	−0.0034 (4)	−0.0031 (4)	−0.0028 (4)
C10	0.0285 (5)	0.0365 (6)	0.0255 (5)	−0.0065 (4)	−0.0017 (4)	−0.0036 (4)
C11	0.0286 (5)	0.0379 (6)	0.0276 (5)	−0.0062 (5)	−0.0005 (4)	−0.0050 (5)
C12	0.0282 (5)	0.0355 (6)	0.0307 (6)	−0.0062 (4)	0.0013 (4)	−0.0070 (5)
C13	0.0361 (6)	0.0446 (7)	0.0270 (5)	−0.0118 (5)	−0.0015 (5)	−0.0046 (5)
C14	0.0335 (6)	0.0520 (8)	0.0312 (6)	−0.0056 (5)	−0.0007 (5)	−0.0109 (5)
C15	0.0317 (6)	0.0432 (7)	0.0285 (5)	−0.0025 (5)	−0.0029 (4)	−0.0090 (5)
C16	0.0424 (7)	0.0480 (8)	0.0405 (7)	−0.0034 (6)	−0.0032 (6)	−0.0149 (6)
C17	0.0566 (9)	0.0605 (10)	0.0527 (9)	0.0029 (8)	−0.0030 (7)	−0.0275 (8)
C18	0.0516 (9)	0.0769 (12)	0.0530 (9)	0.0047 (8)	0.0062 (7)	−0.0312 (9)
C19	0.0396 (7)	0.0755 (11)	0.0428 (8)	−0.0071 (7)	0.0084 (6)	−0.0190 (8)
C20	0.0349 (6)	0.0387 (6)	0.0339 (6)	−0.0119 (5)	0.0037 (5)	−0.0100 (5)
C21	0.0486 (8)	0.0377 (7)	0.0531 (9)	−0.0091 (6)	0.0019 (7)	−0.0051 (6)
C22	0.0836 (13)	0.0398 (8)	0.0603 (10)	−0.0189 (8)	0.0015 (9)	0.0005 (7)
C23	0.0819 (13)	0.0590 (11)	0.0600 (11)	−0.0388 (10)	0.0225 (10)	−0.0105 (9)
C24	0.0466 (9)	0.0712 (12)	0.0680 (11)	−0.0298 (8)	0.0193 (8)	−0.0268 (10)
C25	0.0360 (7)	0.0533 (8)	0.0483 (8)	−0.0140 (6)	0.0025 (6)	−0.0177 (7)
C26	0.0306 (6)	0.0418 (7)	0.0335 (6)	−0.0060 (5)	−0.0007 (5)	−0.0113 (5)
C27	0.0661 (12)	0.0860 (15)	0.0753 (13)	0.0301 (11)	0.0142 (10)	−0.0209 (12)
O1	0.0515 (6)	0.0415 (5)	0.0361 (5)	−0.0080 (4)	−0.0168 (4)	−0.0013 (4)
O2	0.0364 (5)	0.0369 (5)	0.0401 (5)	−0.0104 (4)	0.0090 (4)	−0.0114 (4)
O3	0.0380 (5)	0.0518 (6)	0.0385 (5)	−0.0139 (4)	0.0087 (4)	−0.0108 (4)
O4	0.0623 (7)	0.0433 (6)	0.0423 (6)	−0.0195 (5)	0.0093 (5)	−0.0061 (4)
O5	0.0472 (6)	0.0628 (7)	0.0355 (5)	−0.0051 (5)	0.0094 (4)	−0.0065 (5)
O6	0.0474 (6)	0.0591 (7)	0.0499 (6)	0.0164 (5)	0.0078 (5)	−0.0059 (5)
Cl1	0.0375 (2)	0.0878 (4)	0.1006 (4)	−0.0003 (2)	−0.0181 (2)	−0.0121 (3)

C1—C2	1.371 (2)	C13—O3	1.3753 (17)
C1—C6	1.3938 (19)	C14—O3	1.3700 (18)
C1—H1	0.9300	C14—C15	1.3873 (18)
C2—C3	1.383 (2)	C14—C19	1.388 (2)
C2—H2	0.9300	C15—C16	1.398 (2)
C3—C4	1.379 (2)	C16—C17	1.376 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.3955 (18)	C17—C18	1.390 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.3925 (18)	C18—C19	1.372 (3)
C5—C9	1.5247 (17)	C18—H18	0.9300
C6—O1	1.3634 (16)	C19—H19	0.9300
C7—O1	1.4195 (17)	C20—C21	1.384 (2)
C7—C8	1.5304 (17)	C20—C25	1.3900 (19)
C7—H7A	0.9700	C21—C22	1.389 (2)
C7—H7B	0.9700	C21—H21	0.9300
C8—C26	1.5279 (17)	C22—C23	1.376 (3)
C8—C9	1.5436 (16)	C22—H22	0.9300
C8—C12	1.5497 (17)	C23—C24	1.365 (3)
C9—C10	1.5203 (17)	C23—H23	0.9300
C9—H9	0.9800	C24—C25	1.387 (2)
C10—C11	1.3530 (18)	C24—H24	0.9300
C10—C13	1.4545 (16)	C25—Cl1	1.7404 (18)
C11—O2	1.3499 (14)	C26—O5	1.1959 (16)
C11—C15	1.4455 (18)	C26—O6	1.3180 (18)
C12—O2	1.4449 (15)	C27—O6	1.449 (2)
C12—C20	1.5067 (17)	C27—H27A	0.9600
C12—H12	0.9800	C27—H27B	0.9600
C13—O4	1.2021 (18)	C27—H27C	0.9600
C2—C1—C6	120.12 (14)	O3—C13—C10	118.33 (12)
C2—C1—H1	119.9	O3—C14—C15	120.97 (12)
C6—C1—H1	119.9	O3—C14—C19	117.76 (13)
C1—C2—C3	119.92 (14)	C15—C14—C19	121.24 (14)
C1—C2—H2	120.0	C14—C15—C16	118.92 (13)
C3—C2—H2	120.0	C14—C15—C11	117.02 (12)
C4—C3—C2	119.88 (14)	C16—C15—C11	124.05 (12)
C4—C3—H3	120.1	C17—C16—C15	120.10 (14)
C2—C3—H3	120.1	C17—C16—H16	120.0
C3—C4—C5	121.53 (14)	C15—C16—H16	120.0
C3—C4—H4	119.2	C16—C17—C18	119.80 (16)
C5—C4—H4	119.2	C16—C17—H17	120.1
C6—C5—C4	117.51 (12)	C18—C17—H17	120.1
C6—C5—C9	120.32 (11)	C19—C18—C17	121.11 (15)
C4—C5—C9	121.74 (12)	C19—C18—H18	119.4
O1—C6—C5	123.90 (12)	C17—C18—H18	119.4
O1—C6—C1	115.05 (12)	C18—C19—C14	118.78 (15)
C5—C6—C1	120.98 (12)	C18—C19—H19	120.6
O1—C7—C8	112.52 (11)	C14—C19—H19	120.6
O1—C7—H7A	109.1	C21—C20—C25	117.39 (13)
C8—C7—H7A	109.1	C21—C20—C12	120.77 (12)
O1—C7—H7B	109.1	C25—C20—C12	121.82 (13)
C8—C7—H7B	109.1	C20—C21—C22	121.45 (16)
H7A—C7—H7B	107.8	C20—C21—H21	119.3
C26—C8—C7	108.02 (10)	C22—C21—H21	119.3
C26—C8—C9	112.31 (10)	C23—C22—C21	119.55 (19)
C7—C8—C9	108.42 (10)	C23—C22—H22	120.2
C26—C8—C12	108.12 (10)	C21—C22—H22	120.2
C7—C8—C12	111.28 (10)	C24—C23—C22	120.32 (15)
C9—C8—C12	108.71 (9)	C24—C23—H23	119.8
C10—C9—C5	116.45 (10)	C22—C23—H23	119.8
C10—C9—C8	108.37 (10)	C23—C24—C25	119.77 (17)
C5—C9—C8	107.63 (9)	C23—C24—H24	120.1
C10—C9—H9	108.0	C25—C24—H24	120.1
C5—C9—H9	108.0	C24—C25—C20	121.43 (17)
C8—C9—H9	108.0	C24—C25—Cl1	117.87 (14)
C11—C10—C13	117.87 (11)	C20—C25—Cl1	120.70 (11)
C11—C10—C9	122.10 (10)	O5—C26—O6	123.95 (13)
C13—C10—C9	119.78 (11)	O5—C26—C8	123.17 (13)
O2—C11—C10	124.46 (11)	O6—C26—C8	112.87 (11)
O2—C11—C15	113.05 (11)	O6—C27—H27A	109.5
C10—C11—C15	122.47 (11)	O6—C27—H27B	109.5
O2—C12—C20	106.06 (10)	H27A—C27—H27B	109.5
O2—C12—C8	109.13 (10)	O6—C27—H27C	109.5
C20—C12—C8	115.06 (10)	H27A—C27—H27C	109.5
O2—C12—H12	108.8	H27B—C27—H27C	109.5
C20—C12—H12	108.8	C6—O1—C7	117.78 (10)
C8—C12—H12	108.8	C11—O2—C12	116.06 (10)
O4—C13—O3	115.96 (11)	C14—O3—C13	122.10 (10)
O4—C13—C10	125.69 (13)	C26—O6—C27	115.38 (14)
C6—C1—C2—C3	0.8 (2)	O2—C11—C15—C14	−177.14 (12)
C1—C2—C3—C4	1.3 (2)	C10—C11—C15—C14	1.25 (19)
C2—C3—C4—C5	−3.0 (2)	O2—C11—C15—C16	2.06 (19)
C3—C4—C5—C6	2.3 (2)	C10—C11—C15—C16	−179.55 (13)
C3—C4—C5—C9	174.80 (14)	C14—C15—C16—C17	0.1 (2)
C4—C5—C6—O1	176.77 (12)	C11—C15—C16—C17	−179.04 (14)
C9—C5—C6—O1	4.20 (19)	C15—C16—C17—C18	1.4 (3)
C4—C5—C6—C1	−0.15 (19)	C16—C17—C18—C19	−1.1 (3)
C9—C5—C6—C1	−172.71 (12)	C17—C18—C19—C14	−0.9 (3)
C2—C1—C6—O1	−178.59 (13)	O3—C14—C19—C18	−175.40 (15)
C2—C1—C6—C5	−1.4 (2)	C15—C14—C19—C18	2.5 (2)
O1—C7—C8—C26	−60.63 (13)	O2—C12—C20—C21	40.09 (17)
O1—C7—C8—C9	61.33 (13)	C8—C12—C20—C21	−80.64 (16)
O1—C7—C8—C12	−179.17 (10)	O2—C12—C20—C25	−141.37 (13)
C6—C5—C9—C10	−98.76 (13)	C8—C12—C20—C25	97.89 (15)
C4—C5—C9—C10	89.00 (15)	C25—C20—C21—C22	−3.0 (2)
C6—C5—C9—C8	23.08 (16)	C12—C20—C21—C22	175.57 (16)
C4—C5—C9—C8	−149.17 (12)	C20—C21—C22—C23	1.0 (3)
C26—C8—C9—C10	−166.73 (10)	C21—C22—C23—C24	1.1 (3)
C7—C8—C9—C10	73.98 (12)	C22—C23—C24—C25	−1.0 (3)
C12—C8—C9—C10	−47.12 (12)	C23—C24—C25—C20	−1.1 (3)
C26—C8—C9—C5	66.55 (13)	C23—C24—C25—Cl1	179.17 (15)
C7—C8—C9—C5	−52.74 (13)	C21—C20—C25—C24	3.1 (2)
C12—C8—C9—C5	−173.85 (10)	C12—C20—C25—C24	−175.47 (15)
C5—C9—C10—C11	138.72 (12)	C21—C20—C25—Cl1	−177.20 (12)
C8—C9—C10—C11	17.27 (16)	C12—C20—C25—Cl1	4.2 (2)
C5—C9—C10—C13	−47.09 (15)	C7—C8—C26—O5	−32.65 (17)
C8—C9—C10—C13	−168.54 (11)	C9—C8—C26—O5	−152.17 (13)
C13—C10—C11—O2	−174.11 (12)	C12—C8—C26—O5	87.89 (15)
C9—C10—C11—O2	0.2 (2)	C7—C8—C26—O6	148.50 (12)
C13—C10—C11—C15	7.69 (19)	C9—C8—C26—O6	28.98 (15)
C9—C10—C11—C15	−178.02 (11)	C12—C8—C26—O6	−90.96 (13)
C26—C8—C12—O2	−173.94 (10)	C5—C6—O1—C7	1.24 (19)
C7—C8—C12—O2	−55.46 (13)	C1—C6—O1—C7	178.32 (12)
C9—C8—C12—O2	63.88 (13)	C8—C7—O1—C6	−34.54 (16)
C26—C8—C12—C20	−54.89 (14)	C10—C11—O2—C12	15.68 (18)
C7—C8—C12—C20	63.59 (14)	C15—C11—O2—C12	−165.96 (11)
C9—C8—C12—C20	−177.08 (10)	C20—C12—O2—C11	−171.76 (10)
C11—C10—C13—O4	165.57 (14)	C8—C12—O2—C11	−47.26 (14)
C9—C10—C13—O4	−8.9 (2)	C15—C14—O3—C13	−0.6 (2)
C11—C10—C13—O3	−13.09 (18)	C19—C14—O3—C13	177.27 (13)
C9—C10—C13—O3	172.48 (11)	O4—C13—O3—C14	−168.99 (13)
O3—C14—C15—C16	175.70 (13)	C10—C13—O3—C14	9.80 (19)
C19—C14—C15—C16	−2.1 (2)	O5—C26—O6—C27	−1.6 (2)
O3—C14—C15—C11	−5.06 (19)	C8—C26—O6—C27	177.28 (16)
C19—C14—C15—C11	177.12 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5i	0.93	2.59	3.271 (2)	130
C12—H12···O4ii	0.98	2.53	3.3316 (16)	139
C23—H23···O5iii	0.93	2.47	3.355 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5i	0.93	2.59	3.271 (2)	130
C12—H12⋯O4ii	0.98	2.53	3.3316 (16)	139
C23—H23⋯O5iii	0.93	2.47	3.355 (3)	159

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