17α-Acet-oxy-11β-hy-droxy-6α-methyl-pregn-4-ene-3,20-dione.

The title compound, C(24)H(34)O(5), a fungal-transformed metabolite of the injecta-ble contraceptive medroxyprogesterone acetate, consists of four fused rings (A, B, C and D; steroid labelling). Ring A exists in a half-chair conformation while trans-fused rings B and C adopt chair conformations. The five-membered ring D adopts an envelope conformation with the C atom bound to the methyl group at the flap. In the crystal, adjacent mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds, forming infinite chains along the a axis.

Related literature

For biotransformational studies, see: Manosroi et al. (2006 ▶), Choudhary et al. (2005 ▶). For the crystal structures of closely related compounds, see: Yousuf et al. (2011 ▶, 2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H34O5

M = 402.51

Orthorhombic,

a = 8.2020 (6) Å

b = 9.8957 (8) Å

c = 27.972 (2) Å

V = 2270.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.33 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.974, T max = 0.987

13528 measured reflections

2431 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.101

S = 1.01

2431 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017631/pv2530sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017631/pv2530Isup2.hkl

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

C24H34O5	F(000) = 872
Mr = 402.51	Dx = 1.178 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1475 reflections
a = 8.2020 (6) Å	θ = 2.2–19.5°
b = 9.8957 (8) Å	µ = 0.08 mm−1
c = 27.972 (2) Å	T = 273 K
V = 2270.3 (3) Å3	Block, colorles
Z = 4	0.33 × 0.20 × 0.16 mm

Bruker SMART APEX CCD area-detector diffractometer	2431 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→7
Tmin = 0.974, Tmax = 0.987	k = −11→11
13528 measured reflections	l = −33→32

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.1706P] where P = (Fo2 + 2Fc2)/3
2431 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.14 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
O1	0.6641 (4)	0.1828 (3)	0.17149 (9)	0.0882 (10)
O2	0.3221 (3)	0.1326 (2)	0.39265 (7)	0.0619 (7)
H2A	0.3329	0.1258	0.4217	0.093*
O3	0.0823 (3)	0.60806 (19)	0.42778 (7)	0.0436 (6)
O4	−0.0792 (4)	0.7315 (3)	0.47488 (10)	0.0782 (9)
O5	−0.1463 (4)	0.4106 (3)	0.50772 (7)	0.0625 (7)
C1	0.5406 (4)	0.1962 (3)	0.29492 (11)	0.0468 (8)
H1A	0.5718	0.2906	0.2967	0.056*
H1B	0.5741	0.1532	0.3245	0.056*
C2	0.6306 (4)	0.1302 (4)	0.25352 (12)	0.0552 (9)
H2B	0.7467	0.1461	0.2570	0.066*
H2C	0.6125	0.0334	0.2544	0.066*
C3	0.5756 (5)	0.1838 (3)	0.20657 (13)	0.0537 (9)
C4	0.4080 (4)	0.2317 (3)	0.20399 (12)	0.0498 (9)
H4A	0.3720	0.2666	0.1750	0.060*
C5	0.3024 (4)	0.2291 (3)	0.24025 (10)	0.0370 (7)
C6	0.1224 (4)	0.2521 (3)	0.23329 (10)	0.0420 (8)
H6A	0.0704	0.1634	0.2366	0.050*
C7	0.0494 (4)	0.3411 (3)	0.27257 (9)	0.0385 (7)
H7A	0.0860	0.4333	0.2677	0.046*
H7B	−0.0684	0.3404	0.2694	0.046*
C8	0.0932 (4)	0.2984 (3)	0.32326 (9)	0.0331 (7)
H8A	0.0445	0.2099	0.3299	0.040*
C9	0.2785 (3)	0.2875 (3)	0.32747 (9)	0.0316 (7)
H9A	0.3188	0.3765	0.3176	0.038*
C10	0.3551 (4)	0.1871 (3)	0.29062 (10)	0.0358 (7)
C11	0.3415 (4)	0.2700 (3)	0.37900 (10)	0.0444 (8)
H11A	0.4587	0.2894	0.3787	0.053*
C12	0.2616 (4)	0.3688 (3)	0.41426 (10)	0.0414 (8)
H12A	0.2937	0.3447	0.4465	0.050*
H12B	0.3017	0.4593	0.4079	0.050*
C13	0.0766 (4)	0.3693 (3)	0.41118 (10)	0.0353 (7)
C14	0.0284 (4)	0.4012 (3)	0.35941 (9)	0.0315 (7)
H14A	0.0796	0.4878	0.3515	0.038*
C15	−0.1546 (4)	0.4277 (3)	0.36200 (10)	0.0436 (8)
H15A	−0.2156	0.3438	0.3603	0.052*
H15B	−0.1895	0.4866	0.3362	0.052*
C16	−0.1776 (4)	0.4969 (3)	0.41121 (10)	0.0446 (8)
H16A	−0.2088	0.5907	0.4070	0.053*
H16B	−0.2622	0.4515	0.4294	0.053*
C17	−0.0141 (4)	0.4875 (3)	0.43735 (10)	0.0387 (8)
C18	0.0023 (4)	0.2353 (3)	0.42872 (11)	0.0505 (9)
H18A	0.0294	0.1644	0.4067	0.076*
H18B	−0.1140	0.2441	0.4307	0.076*
H18C	0.0453	0.2138	0.4597	0.076*
C19	0.3006 (4)	0.0393 (3)	0.29747 (12)	0.0489 (9)
H19A	0.3279	−0.0120	0.2695	0.073*
H19B	0.1849	0.0364	0.3025	0.073*
H19C	0.3552	0.0015	0.3247	0.073*
C20	−0.0259 (5)	0.4646 (3)	0.49130 (11)	0.0468 (9)
C21	0.1183 (5)	0.4973 (4)	0.52202 (11)	0.0694 (12)
H21A	0.0824	0.5434	0.5503	0.104*
H21B	0.1921	0.5543	0.5046	0.104*
H21C	0.1729	0.4152	0.5308	0.104*
C22	0.0342 (5)	0.7246 (3)	0.44810 (12)	0.0529 (9)
C23	0.1423 (6)	0.8383 (3)	0.43387 (14)	0.0734 (12)
H23A	0.0804	0.9206	0.4329	0.110*
H23B	0.1873	0.8206	0.4028	0.110*
H23C	0.2291	0.8472	0.4567	0.110*
C24	0.0737 (5)	0.3052 (4)	0.18406 (11)	0.0640 (11)
H24A	0.1168	0.2466	0.1598	0.096*
H24B	0.1167	0.3946	0.1798	0.096*
H24C	−0.0430	0.3078	0.1816	0.096*

	U11	U22	U33	U12	U13	U23
O1	0.074 (2)	0.112 (2)	0.0788 (19)	0.0133 (19)	0.0404 (17)	−0.0020 (17)
O2	0.099 (2)	0.0503 (14)	0.0370 (12)	0.0260 (15)	−0.0086 (14)	0.0050 (10)
O3	0.0552 (15)	0.0343 (11)	0.0412 (12)	−0.0046 (11)	0.0072 (10)	−0.0033 (9)
O4	0.094 (2)	0.0631 (17)	0.0772 (18)	0.0083 (17)	0.0248 (17)	−0.0216 (15)
O5	0.081 (2)	0.0647 (16)	0.0420 (13)	−0.0101 (15)	0.0218 (13)	0.0063 (11)
C1	0.037 (2)	0.0492 (19)	0.054 (2)	0.0016 (18)	−0.0014 (16)	−0.0095 (16)
C2	0.038 (2)	0.056 (2)	0.071 (2)	0.0063 (17)	0.0059 (18)	−0.0132 (19)
C3	0.050 (2)	0.051 (2)	0.060 (2)	−0.0005 (19)	0.014 (2)	−0.0104 (17)
C4	0.051 (2)	0.0498 (19)	0.0481 (19)	−0.0005 (17)	0.0079 (17)	−0.0028 (16)
C5	0.043 (2)	0.0314 (15)	0.0365 (16)	0.0003 (15)	0.0038 (15)	−0.0045 (13)
C6	0.043 (2)	0.0492 (19)	0.0342 (16)	−0.0006 (16)	−0.0056 (14)	−0.0050 (14)
C7	0.0350 (19)	0.0440 (17)	0.0364 (17)	0.0029 (16)	−0.0041 (14)	−0.0025 (13)
C8	0.0358 (19)	0.0327 (15)	0.0307 (15)	−0.0036 (14)	0.0014 (13)	−0.0003 (13)
C9	0.0303 (18)	0.0312 (15)	0.0334 (15)	0.0000 (14)	−0.0012 (12)	0.0023 (13)
C10	0.0339 (19)	0.0341 (16)	0.0395 (16)	0.0014 (15)	−0.0026 (14)	−0.0046 (13)
C11	0.048 (2)	0.0449 (18)	0.0406 (17)	0.0092 (17)	−0.0057 (16)	−0.0037 (15)
C12	0.048 (2)	0.0453 (19)	0.0311 (16)	0.0030 (16)	−0.0076 (14)	−0.0013 (15)
C13	0.042 (2)	0.0348 (16)	0.0294 (15)	−0.0015 (15)	0.0043 (14)	0.0017 (13)
C14	0.033 (2)	0.0310 (14)	0.0306 (15)	−0.0008 (14)	0.0007 (13)	0.0013 (12)
C15	0.037 (2)	0.0497 (19)	0.0442 (18)	0.0005 (16)	0.0013 (16)	−0.0033 (15)
C16	0.046 (2)	0.0473 (19)	0.0404 (18)	0.0013 (18)	0.0096 (17)	−0.0001 (15)
C17	0.047 (2)	0.0360 (16)	0.0328 (17)	−0.0033 (15)	0.0062 (15)	0.0056 (13)
C18	0.066 (3)	0.0397 (18)	0.0459 (18)	−0.0063 (17)	0.0062 (17)	0.0076 (15)
C19	0.055 (2)	0.0379 (17)	0.0534 (19)	0.0024 (17)	0.0007 (18)	−0.0057 (15)
C20	0.066 (3)	0.0411 (18)	0.0338 (17)	0.0042 (19)	0.0106 (17)	0.0015 (14)
C21	0.087 (3)	0.085 (3)	0.036 (2)	0.002 (3)	−0.003 (2)	−0.0006 (19)
C22	0.074 (3)	0.0394 (19)	0.0450 (19)	0.005 (2)	−0.0062 (19)	−0.0075 (16)
C23	0.105 (4)	0.042 (2)	0.073 (3)	−0.015 (2)	−0.012 (2)	0.0018 (18)
C24	0.065 (3)	0.088 (3)	0.0385 (19)	0.023 (2)	−0.0089 (17)	−0.0116 (19)

O1—C3	1.220 (4)	C11—H11A	0.9800
O2—C11	1.421 (4)	C12—C13	1.519 (4)
O2—H2A	0.8199	C12—H12A	0.9700
O3—C22	1.344 (4)	C12—H12B	0.9700
O3—C17	1.456 (3)	C13—C14	1.534 (4)
O4—C22	1.196 (4)	C13—C18	1.540 (4)
O5—C20	1.213 (4)	C13—C17	1.567 (4)
C1—C2	1.521 (4)	C14—C15	1.525 (4)
C1—C10	1.529 (4)	C14—H14A	0.9800
C1—H1A	0.9700	C15—C16	1.549 (4)
C1—H1B	0.9700	C15—H15A	0.9700
C2—C3	1.486 (5)	C15—H15B	0.9700
C2—H2B	0.9700	C16—C17	1.531 (4)
C2—H2C	0.9700	C16—H16A	0.9700
C3—C4	1.456 (5)	C16—H16B	0.9700
C4—C5	1.334 (4)	C17—C20	1.529 (4)
C4—H4A	0.9300	C18—H18A	0.9600
C5—C6	1.507 (4)	C18—H18B	0.9600
C5—C10	1.531 (4)	C18—H18C	0.9600
C6—C24	1.527 (4)	C19—H19A	0.9600
C6—C7	1.530 (4)	C19—H19B	0.9600
C6—H6A	0.9800	C19—H19C	0.9600
C7—C8	1.523 (4)	C20—C21	1.497 (5)
C7—H7A	0.9700	C21—H21A	0.9600
C7—H7B	0.9700	C21—H21B	0.9600
C8—C9	1.528 (4)	C21—H21C	0.9600
C8—C14	1.530 (4)	C22—C23	1.487 (5)
C8—H8A	0.9800	C23—H23A	0.9600
C9—C11	1.541 (4)	C23—H23B	0.9600
C9—C10	1.563 (4)	C23—H23C	0.9600
C9—H9A	0.9800	C24—H24A	0.9600
C10—C19	1.541 (4)	C24—H24B	0.9600
C11—C12	1.536 (4)	C24—H24C	0.9600
C11—O2—H2A	109.5	C12—C13—C18	112.0 (3)
C22—O3—C17	117.8 (3)	C14—C13—C18	112.1 (2)
C2—C1—C10	113.5 (3)	C12—C13—C17	116.8 (3)
C2—C1—H1A	108.9	C14—C13—C17	99.5 (2)
C10—C1—H1A	108.9	C18—C13—C17	107.8 (2)
C2—C1—H1B	108.9	C15—C14—C8	119.2 (2)
C10—C1—H1B	108.9	C15—C14—C13	104.1 (2)
H1A—C1—H1B	107.7	C8—C14—C13	113.4 (2)
C3—C2—C1	111.9 (3)	C15—C14—H14A	106.4
C3—C2—H2B	109.2	C8—C14—H14A	106.4
C1—C2—H2B	109.2	C13—C14—H14A	106.4
C3—C2—H2C	109.2	C14—C15—C16	103.8 (2)
C1—C2—H2C	109.2	C14—C15—H15A	111.0
H2B—C2—H2C	107.9	C16—C15—H15A	111.0
O1—C3—C4	121.6 (4)	C14—C15—H15B	111.0
O1—C3—C2	121.8 (3)	C16—C15—H15B	111.0
C4—C3—C2	116.5 (3)	H15A—C15—H15B	109.0
C5—C4—C3	124.7 (3)	C17—C16—C15	106.9 (3)
C5—C4—H4A	117.7	C17—C16—H16A	110.3
C3—C4—H4A	117.7	C15—C16—H16A	110.3
C4—C5—C6	122.4 (3)	C17—C16—H16B	110.3
C4—C5—C10	121.4 (3)	C15—C16—H16B	110.3
C6—C5—C10	115.9 (2)	H16A—C16—H16B	108.6
C5—C6—C24	115.1 (3)	O3—C17—C20	109.7 (2)
C5—C6—C7	112.2 (2)	O3—C17—C16	109.7 (2)
C24—C6—C7	110.3 (3)	C20—C17—C16	115.2 (3)
C5—C6—H6A	106.2	O3—C17—C13	105.5 (2)
C24—C6—H6A	106.2	C20—C17—C13	112.4 (2)
C7—C6—H6A	106.2	C16—C17—C13	103.8 (2)
C8—C7—C6	114.6 (2)	C13—C18—H18A	109.5
C8—C7—H7A	108.6	C13—C18—H18B	109.5
C6—C7—H7A	108.6	H18A—C18—H18B	109.5
C8—C7—H7B	108.6	C13—C18—H18C	109.5
C6—C7—H7B	108.6	H18A—C18—H18C	109.5
H7A—C7—H7B	107.6	H18B—C18—H18C	109.5
C7—C8—C9	109.0 (2)	C10—C19—H19A	109.5
C7—C8—C14	110.4 (2)	C10—C19—H19B	109.5
C9—C8—C14	110.0 (2)	H19A—C19—H19B	109.5
C7—C8—H8A	109.1	C10—C19—H19C	109.5
C9—C8—H8A	109.1	H19A—C19—H19C	109.5
C14—C8—H8A	109.1	H19B—C19—H19C	109.5
C8—C9—C11	114.4 (2)	O5—C20—C21	121.4 (3)
C8—C9—C10	113.2 (2)	O5—C20—C17	119.4 (3)
C11—C9—C10	114.2 (2)	C21—C20—C17	119.0 (3)
C8—C9—H9A	104.5	C20—C21—H21A	109.5
C11—C9—H9A	104.5	C20—C21—H21B	109.5
C10—C9—H9A	104.5	H21A—C21—H21B	109.5
C1—C10—C5	109.7 (3)	C20—C21—H21C	109.5
C1—C10—C19	109.5 (3)	H21A—C21—H21C	109.5
C5—C10—C19	106.8 (2)	H21B—C21—H21C	109.5
C1—C10—C9	108.1 (2)	O4—C22—O3	122.8 (3)
C5—C10—C9	108.7 (2)	O4—C22—C23	126.0 (3)
C19—C10—C9	113.9 (2)	O3—C22—C23	111.2 (3)
O2—C11—C12	112.9 (3)	C22—C23—H23A	109.5
O2—C11—C9	108.7 (2)	C22—C23—H23B	109.5
C12—C11—C9	112.7 (2)	H23A—C23—H23B	109.5
O2—C11—H11A	107.4	C22—C23—H23C	109.5
C12—C11—H11A	107.4	H23A—C23—H23C	109.5
C9—C11—H11A	107.4	H23B—C23—H23C	109.5
C13—C12—C11	113.1 (3)	C6—C24—H24A	109.5
C13—C12—H12A	109.0	C6—C24—H24B	109.5
C11—C12—H12A	109.0	H24A—C24—H24B	109.5
C13—C12—H12B	109.0	C6—C24—H24C	109.5
C11—C12—H12B	109.0	H24A—C24—H24C	109.5
H12A—C12—H12B	107.8	H24B—C24—H24C	109.5
C12—C13—C14	108.2 (2)
C10—C1—C2—C3	54.1 (4)	C11—C12—C13—C14	−56.1 (3)
C1—C2—C3—O1	153.9 (4)	C11—C12—C13—C18	67.9 (3)
C1—C2—C3—C4	−28.9 (4)	C11—C12—C13—C17	−167.2 (2)
O1—C3—C4—C5	176.4 (4)	C7—C8—C14—C15	60.3 (3)
C2—C3—C4—C5	−0.8 (5)	C9—C8—C14—C15	−179.4 (3)
C3—C4—C5—C6	−166.9 (3)	C7—C8—C14—C13	−176.6 (2)
C3—C4—C5—C10	6.4 (5)	C9—C8—C14—C13	−56.2 (3)
C4—C5—C6—C24	−11.3 (5)	C12—C13—C14—C15	−168.9 (2)
C10—C5—C6—C24	175.1 (3)	C18—C13—C14—C15	67.2 (3)
C4—C5—C6—C7	−138.6 (3)	C17—C13—C14—C15	−46.5 (3)
C10—C5—C6—C7	47.9 (4)	C12—C13—C14—C8	60.0 (3)
C5—C6—C7—C8	−49.1 (4)	C18—C13—C14—C8	−63.9 (3)
C24—C6—C7—C8	−178.9 (3)	C17—C13—C14—C8	−177.6 (2)
C6—C7—C8—C9	53.6 (3)	C8—C14—C15—C16	162.3 (2)
C6—C7—C8—C14	174.5 (2)	C13—C14—C15—C16	34.7 (3)
C7—C8—C9—C11	169.6 (2)	C14—C15—C16—C17	−8.4 (3)
C14—C8—C9—C11	48.4 (3)	C22—O3—C17—C20	−56.0 (4)
C7—C8—C9—C10	−57.2 (3)	C22—O3—C17—C16	71.5 (3)
C14—C8—C9—C10	−178.4 (2)	C22—O3—C17—C13	−177.3 (3)
C2—C1—C10—C5	−47.7 (4)	C15—C16—C17—O3	92.2 (3)
C2—C1—C10—C19	69.3 (3)	C15—C16—C17—C20	−143.4 (3)
C2—C1—C10—C9	−166.1 (2)	C15—C16—C17—C13	−20.2 (3)
C4—C5—C10—C1	18.1 (4)	C12—C13—C17—O3	41.0 (3)
C6—C5—C10—C1	−168.3 (3)	C14—C13—C17—O3	−75.0 (3)
C4—C5—C10—C19	−100.6 (3)	C18—C13—C17—O3	168.0 (2)
C6—C5—C10—C19	73.0 (3)	C12—C13—C17—C20	−78.5 (3)
C4—C5—C10—C9	136.1 (3)	C14—C13—C17—C20	165.5 (3)
C6—C5—C10—C9	−50.2 (3)	C18—C13—C17—C20	48.5 (3)
C8—C9—C10—C1	174.2 (3)	C12—C13—C17—C16	156.4 (3)
C11—C9—C10—C1	−52.4 (3)	C14—C13—C17—C16	40.4 (3)
C8—C9—C10—C5	55.2 (3)	C18—C13—C17—C16	−76.6 (3)
C11—C9—C10—C5	−171.5 (3)	O3—C17—C20—O5	149.5 (3)
C8—C9—C10—C19	−63.8 (3)	C16—C17—C20—O5	25.1 (4)
C11—C9—C10—C19	69.5 (3)	C13—C17—C20—O5	−93.5 (4)
C8—C9—C11—O2	79.6 (3)	O3—C17—C20—C21	−36.3 (4)
C10—C9—C11—O2	−53.2 (4)	C16—C17—C20—C21	−160.7 (3)
C8—C9—C11—C12	−46.4 (4)	C13—C17—C20—C21	80.8 (4)
C10—C9—C11—C12	−179.1 (3)	C17—O3—C22—O4	3.1 (5)
O2—C11—C12—C13	−73.2 (3)	C17—O3—C22—C23	−178.5 (3)
C9—C11—C12—C13	50.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O5i	0.82	2.01	2.831 (3)	174
C23—H23C···O4ii	0.96	2.60	3.494 (5)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O5i	0.82	2.01	2.831 (3)	174
C23—H23C⋯O4ii	0.96	2.60	3.494 (5)	156

Symmetry codes: (i) ; (ii) .