Redetermination and absolute configuration of atalaphylline.

THE TITLE ACRIDONE ALKALOID [SYSTEMATIC NAME: 1,3,5-trihydr-oxy-2,4-bis-(3-methyl-but-2-en-yl)acridin-9(10H)-one], C(23)H(25)NO(4), has previously been reported as crystallizing in the chiral ortho-rhom-bic space group P2(1)2(1)2(1) [Chantrapromma et al. (2010 ▶). Acta Cryst. E66, o81-o82] but the absolute configuration could not be determined from data collected with Mo radiation. The absolute configuration has now been determined by refinement of the Flack parameter with data collected using Cu radiation. All features of the mol-ecule and its crystal packing are similar to those previously described.

Related literature

For details of acridone alkaloids see: Basu & Basa (1972 ▶). For the previous structure determination, see: Chantrapromma et al. (2010 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C23H25NO4

M = 379.44

Orthorhombic,

a = 5.0838 (1) Å

b = 15.0262 (3) Å

c = 24.6412 (4) Å

V = 1882.35 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.74 mm−1

T = 150 K

0.40 × 0.21 × 0.04 mm

Data collection

Bruker APEX Duo CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.755, T max = 0.970

11768 measured reflections

3145 independent reflections

3099 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.068

S = 1.06

3145 reflections

354 parameters

All H-atom parameters refined

Δρmax = 0.12 e Å−3

Δρmin = −0.10 e Å−3

Absolute structure: Flack (1983 ▶), 1280 Friedel pairs

Flack parameter: 0.05 (13)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905449X/sj2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905449X/sj2714Isup2.hkl

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

C23H25NO4	F(000) = 808
Mr = 379.44	Dx = 1.339 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3145 reflections
a = 5.0838 (1) Å	θ = 6.1–64.9°
b = 15.0262 (3) Å	µ = 0.74 mm−1
c = 24.6412 (4) Å	T = 150 K
V = 1882.35 (6) Å3	Plate, brown
Z = 4	0.40 × 0.21 × 0.04 mm

Bruker APEX Duo CCD area-detector diffractometer	3145 independent reflections
Radiation source: sealed tube	3099 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 64.9°, θmin = 6.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.755, Tmax = 0.970	k = −17→17
11768 measured reflections	l = −28→28

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.1806P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.068	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.12 e Å−3
3145 reflections	Δρmin = −0.10 e Å−3
354 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0020 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1280 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.05 (13)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 150.0 (1) K.

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 > 2sigma(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	0.33887 (19)	0.33672 (5)	0.16257 (4)	0.0319 (2)
H1O1	0.469 (4)	0.3351 (12)	0.1882 (7)	0.049 (5)*
O2	0.72372 (18)	0.37879 (5)	0.22397 (3)	0.0312 (2)
O3	0.90459 (19)	0.77102 (5)	0.22853 (3)	0.0318 (2)
H1O3	0.997 (4)	0.8077 (12)	0.2462 (7)	0.044 (4)*
O4	−0.06425 (19)	0.56721 (6)	0.06026 (4)	0.0361 (2)
H1O4	−0.139 (5)	0.5215 (14)	0.0460 (8)	0.063 (6)*
N1	0.6200 (2)	0.63969 (6)	0.18325 (4)	0.0264 (2)
H1N1	0.606 (4)	0.6957 (12)	0.1732 (6)	0.038 (4)*
C1	0.1336 (2)	0.44827 (8)	0.11088 (5)	0.0273 (3)
C2	0.3211 (2)	0.42334 (8)	0.14856 (5)	0.0261 (3)
C3	0.4921 (2)	0.48690 (7)	0.17304 (4)	0.0251 (3)
C4	0.6888 (2)	0.46022 (8)	0.21176 (5)	0.0262 (3)
C5	0.8448 (3)	0.52966 (8)	0.23719 (5)	0.0269 (3)
C6	1.0361 (3)	0.50956 (8)	0.27663 (5)	0.0331 (3)
H6A	1.074 (3)	0.4477 (10)	0.2852 (6)	0.030 (3)*
C7	1.1787 (3)	0.57660 (9)	0.29998 (6)	0.0381 (3)
H7A	1.318 (4)	0.5600 (11)	0.3267 (7)	0.045 (4)*
C8	1.1372 (3)	0.66535 (9)	0.28512 (5)	0.0343 (3)
H8A	1.240 (4)	0.7140 (12)	0.3021 (7)	0.057 (5)*
C9	0.9535 (3)	0.68681 (8)	0.24628 (5)	0.0281 (3)
C10	0.8034 (2)	0.61840 (8)	0.22173 (5)	0.0259 (3)
C11	0.4625 (2)	0.57783 (7)	0.15855 (5)	0.0255 (2)
C12	0.2744 (2)	0.60509 (8)	0.12029 (5)	0.0274 (3)
C13	0.1178 (2)	0.53936 (8)	0.09727 (5)	0.0277 (3)
C14	0.2289 (3)	0.70240 (8)	0.10748 (6)	0.0319 (3)
H14A	0.081 (4)	0.7041 (11)	0.0827 (7)	0.049 (5)*
H14B	0.184 (3)	0.7325 (11)	0.1402 (7)	0.040 (4)*
C15	0.4574 (3)	0.74968 (8)	0.08153 (5)	0.0313 (3)
H15A	0.544 (3)	0.7170 (10)	0.0517 (6)	0.041 (4)*
C16	0.5452 (3)	0.83055 (8)	0.09368 (5)	0.0346 (3)
C17	0.7648 (4)	0.87331 (12)	0.06276 (8)	0.0536 (4)
H17A	0.917 (5)	0.8886 (16)	0.0890 (10)	0.087 (7)*
H17B	0.829 (4)	0.8328 (14)	0.0332 (8)	0.065 (6)*
H17C	0.715 (4)	0.9270 (13)	0.0451 (7)	0.053 (5)*
C18	0.4364 (4)	0.88686 (9)	0.13869 (7)	0.0469 (4)
H18A	0.281 (5)	0.8592 (14)	0.1596 (9)	0.071 (6)*
H18B	0.563 (6)	0.8967 (17)	0.1648 (10)	0.096 (8)*
H18C	0.371 (4)	0.9448 (14)	0.1242 (8)	0.063 (5)*
C19	−0.0548 (3)	0.38053 (8)	0.08652 (5)	0.0301 (3)
H19A	−0.048 (3)	0.3304 (11)	0.1104 (6)	0.039 (4)*
H19B	−0.240 (4)	0.4055 (10)	0.0883 (6)	0.042 (4)*
C20	0.0167 (3)	0.35223 (7)	0.02981 (5)	0.0312 (3)
H20A	0.179 (3)	0.3171 (10)	0.0264 (6)	0.037 (4)*
C21	−0.1104 (3)	0.37003 (8)	−0.01615 (5)	0.0351 (3)
C22	−0.0091 (4)	0.33621 (11)	−0.06969 (6)	0.0509 (4)
H22A	−0.149 (5)	0.3035 (14)	−0.0897 (8)	0.069 (6)*
H22B	0.043 (4)	0.3915 (13)	−0.0939 (8)	0.061 (5)*
H22C	0.179 (5)	0.2984 (15)	−0.0653 (9)	0.080 (7)*
C23	−0.3525 (3)	0.42646 (13)	−0.02079 (7)	0.0520 (4)
H23A	−0.490 (5)	0.3962 (16)	−0.0444 (9)	0.083 (7)*
H23B	−0.312 (6)	0.4882 (19)	−0.0386 (10)	0.099 (8)*
H23C	−0.438 (4)	0.4365 (11)	0.0152 (8)	0.050 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0368 (5)	0.0218 (4)	0.0370 (5)	−0.0033 (3)	−0.0036 (4)	−0.0006 (3)
O2	0.0342 (5)	0.0199 (4)	0.0395 (5)	0.0001 (4)	−0.0059 (4)	0.0012 (3)
O3	0.0387 (5)	0.0210 (4)	0.0357 (4)	−0.0020 (4)	−0.0080 (4)	−0.0015 (3)
O4	0.0340 (5)	0.0337 (5)	0.0406 (5)	−0.0034 (4)	−0.0116 (4)	0.0020 (4)
N1	0.0280 (5)	0.0194 (5)	0.0318 (5)	−0.0012 (4)	−0.0023 (4)	−0.0003 (4)
C1	0.0269 (6)	0.0283 (6)	0.0266 (5)	−0.0036 (5)	0.0034 (5)	−0.0033 (4)
C2	0.0280 (6)	0.0228 (5)	0.0275 (5)	−0.0009 (5)	0.0051 (5)	−0.0020 (4)
C3	0.0253 (6)	0.0234 (5)	0.0266 (5)	−0.0007 (5)	0.0032 (5)	−0.0022 (4)
C4	0.0271 (6)	0.0234 (5)	0.0280 (5)	0.0009 (4)	0.0023 (5)	−0.0008 (4)
C5	0.0286 (6)	0.0229 (6)	0.0290 (6)	−0.0007 (5)	0.0010 (5)	−0.0014 (4)
C6	0.0396 (7)	0.0238 (6)	0.0358 (6)	0.0027 (5)	−0.0084 (6)	0.0009 (5)
C7	0.0438 (8)	0.0299 (6)	0.0405 (7)	−0.0008 (6)	−0.0164 (6)	−0.0005 (5)
C8	0.0402 (7)	0.0271 (6)	0.0356 (7)	−0.0038 (5)	−0.0096 (6)	−0.0039 (5)
C9	0.0324 (7)	0.0222 (5)	0.0298 (6)	−0.0015 (5)	0.0004 (5)	−0.0027 (4)
C10	0.0261 (6)	0.0254 (6)	0.0263 (6)	0.0013 (5)	0.0012 (5)	−0.0011 (4)
C11	0.0245 (6)	0.0234 (5)	0.0285 (6)	−0.0012 (5)	0.0028 (5)	−0.0016 (4)
C12	0.0254 (6)	0.0261 (6)	0.0306 (6)	0.0000 (5)	0.0001 (5)	−0.0003 (5)
C13	0.0255 (6)	0.0295 (6)	0.0281 (5)	−0.0004 (5)	0.0012 (5)	0.0012 (5)
C14	0.0286 (7)	0.0269 (6)	0.0403 (7)	0.0007 (5)	−0.0047 (6)	0.0011 (5)
C15	0.0329 (7)	0.0300 (6)	0.0310 (6)	0.0029 (6)	−0.0039 (5)	0.0032 (5)
C16	0.0325 (7)	0.0297 (6)	0.0414 (7)	−0.0017 (5)	−0.0116 (6)	0.0106 (5)
C17	0.0408 (8)	0.0440 (8)	0.0759 (12)	−0.0058 (7)	−0.0023 (8)	0.0237 (8)
C18	0.0621 (10)	0.0288 (6)	0.0497 (8)	−0.0040 (7)	−0.0127 (8)	−0.0037 (6)
C19	0.0311 (7)	0.0291 (6)	0.0300 (6)	−0.0058 (6)	−0.0005 (5)	−0.0009 (5)
C20	0.0338 (7)	0.0245 (5)	0.0353 (6)	−0.0031 (5)	0.0022 (5)	−0.0027 (5)
C21	0.0413 (7)	0.0318 (6)	0.0323 (6)	−0.0113 (6)	−0.0007 (6)	−0.0002 (5)
C22	0.0705 (11)	0.0481 (8)	0.0341 (7)	−0.0124 (8)	0.0028 (7)	−0.0042 (6)
C23	0.0417 (8)	0.0680 (11)	0.0465 (9)	0.0000 (8)	−0.0128 (7)	−0.0005 (8)

O1—C2	1.3497 (15)	C12—C14	1.5137 (16)
O1—H1O1	0.92 (2)	C14—C15	1.5045 (18)
O2—C4	1.2725 (14)	C14—H14A	0.97 (2)
O3—C9	1.3617 (14)	C14—H14B	0.954 (16)
O3—H1O3	0.845 (19)	C15—C16	1.3285 (18)
O4—C13	1.3651 (15)	C15—H15A	0.986 (16)
O4—H1O4	0.86 (2)	C16—C17	1.497 (2)
N1—C10	1.3679 (16)	C16—C18	1.501 (2)
N1—C11	1.3695 (15)	C17—H17A	1.03 (3)
N1—H1N1	0.880 (17)	C17—H17B	1.00 (2)
C1—C2	1.3825 (18)	C17—H17C	0.95 (2)
C1—C13	1.4114 (17)	C18—H18A	1.03 (2)
C1—C19	1.5209 (16)	C18—H18B	0.92 (3)
C2—C3	1.4254 (16)	C18—H18C	1.00 (2)
C3—C11	1.4203 (16)	C19—C20	1.5051 (17)
C3—C4	1.4393 (17)	C19—H19A	0.957 (16)
C4—C5	1.4525 (16)	C19—H19B	1.015 (19)
C5—C10	1.4026 (17)	C20—C21	1.3311 (19)
C5—C6	1.4078 (18)	C20—H20A	0.982 (17)
C6—C7	1.3679 (19)	C21—C23	1.499 (2)
C6—H6A	0.973 (15)	C21—C22	1.505 (2)
C7—C8	1.3990 (19)	C22—H22A	0.99 (2)
C7—H7A	0.997 (18)	C22—H22B	1.06 (2)
C8—C9	1.3754 (18)	C22—H22C	1.12 (3)
C8—H8A	0.99 (2)	C23—H23A	1.02 (3)
C9—C10	1.4159 (17)	C23—H23B	1.05 (3)
C11—C12	1.4041 (17)	C23—H23C	0.999 (19)
C12—C13	1.3895 (17)
C2—O1—H1O1	104.5 (11)	C12—C14—H14A	106.0 (10)
C9—O3—H1O3	109.9 (12)	C15—C14—H14B	108.8 (10)
C13—O4—H1O4	109.2 (14)	C12—C14—H14B	108.6 (10)
C10—N1—C11	123.22 (10)	H14A—C14—H14B	109.5 (14)
C10—N1—H1N1	118.3 (11)	C16—C15—C14	126.55 (13)
C11—N1—H1N1	118.5 (11)	C16—C15—H15A	118.3 (10)
C2—C1—C13	117.48 (11)	C14—C15—H15A	115.1 (9)
C2—C1—C19	121.19 (11)	C15—C16—C17	121.91 (15)
C13—C1—C19	121.29 (11)	C15—C16—C18	123.95 (13)
O1—C2—C1	118.64 (10)	C17—C16—C18	114.14 (14)
O1—C2—C3	119.81 (11)	C16—C17—H17A	109.5 (14)
C1—C2—C3	121.55 (11)	C16—C17—H17B	110.5 (12)
C11—C3—C2	118.26 (10)	H17A—C17—H17B	110.4 (19)
C11—C3—C4	120.55 (10)	C16—C17—H17C	113.6 (12)
C2—C3—C4	121.18 (10)	H17A—C17—H17C	107.3 (17)
O2—C4—C3	121.43 (11)	H17B—C17—H17C	105.5 (16)
O2—C4—C5	120.84 (11)	C16—C18—H18A	115.1 (12)
C3—C4—C5	117.72 (10)	C16—C18—H18B	110.4 (17)
C10—C5—C6	119.67 (11)	H18A—C18—H18B	104.6 (18)
C10—C5—C4	118.94 (11)	C16—C18—H18C	110.5 (11)
C6—C5—C4	121.39 (11)	H18A—C18—H18C	105.9 (17)
C7—C6—C5	119.90 (12)	H18B—C18—H18C	110 (2)
C7—C6—H6A	120.5 (9)	C20—C19—C1	113.79 (10)
C5—C6—H6A	119.5 (9)	C20—C19—H19A	109.9 (9)
C6—C7—C8	120.79 (12)	C1—C19—H19A	105.1 (10)
C6—C7—H7A	118.0 (10)	C20—C19—H19B	111.7 (9)
C8—C7—H7A	121.2 (10)	C1—C19—H19B	108.6 (9)
C9—C8—C7	120.54 (12)	H19A—C19—H19B	107.4 (14)
C9—C8—H8A	118.7 (11)	C21—C20—C19	128.01 (13)
C7—C8—H8A	120.8 (11)	C21—C20—H20A	116.2 (9)
O3—C9—C8	124.42 (11)	C19—C20—H20A	115.8 (9)
O3—C9—C10	116.04 (11)	C20—C21—C23	125.26 (13)
C8—C9—C10	119.53 (11)	C20—C21—C22	120.79 (14)
N1—C10—C5	120.86 (11)	C23—C21—C22	113.91 (14)
N1—C10—C9	119.58 (11)	C21—C22—H22A	110.9 (12)
C5—C10—C9	119.56 (11)	C21—C22—H22B	108.4 (10)
N1—C11—C12	119.91 (10)	H22A—C22—H22B	106.7 (15)
N1—C11—C3	118.64 (11)	C21—C22—H22C	112.3 (11)
C12—C11—C3	121.44 (10)	H22A—C22—H22C	114.1 (16)
C13—C12—C11	117.19 (11)	H22B—C22—H22C	103.9 (16)
C13—C12—C14	120.93 (11)	C21—C23—H23A	110.8 (14)
C11—C12—C14	121.73 (11)	C21—C23—H23B	111.8 (17)
O4—C13—C12	116.30 (11)	H23A—C23—H23B	107 (2)
O4—C13—C1	119.64 (11)	C21—C23—H23C	112.1 (11)
C12—C13—C1	124.04 (11)	H23A—C23—H23C	106.0 (17)
C15—C14—C12	115.26 (11)	H23B—C23—H23C	108.9 (17)
C15—C14—H14A	108.6 (10)
C13—C1—C2—O1	179.51 (10)	O3—C9—C10—C5	179.04 (11)
C19—C1—C2—O1	1.60 (17)	C8—C9—C10—C5	−0.24 (18)
C13—C1—C2—C3	0.19 (17)	C10—N1—C11—C12	178.53 (10)
C19—C1—C2—C3	−177.72 (10)	C10—N1—C11—C3	−0.68 (17)
O1—C2—C3—C11	−178.11 (10)	C2—C3—C11—N1	177.81 (10)
C1—C2—C3—C11	1.20 (17)	C4—C3—C11—N1	−1.72 (16)
O1—C2—C3—C4	1.42 (16)	C2—C3—C11—C12	−1.39 (16)
C1—C2—C3—C4	−179.27 (11)	C4—C3—C11—C12	179.08 (11)
C11—C3—C4—O2	−177.79 (11)	N1—C11—C12—C13	−179.03 (11)
C2—C3—C4—O2	2.69 (17)	C3—C11—C12—C13	0.16 (17)
C11—C3—C4—C5	3.05 (16)	N1—C11—C12—C14	−3.44 (17)
C2—C3—C4—C5	−176.47 (10)	C3—C11—C12—C14	175.74 (11)
O2—C4—C5—C10	178.75 (11)	C11—C12—C13—O4	179.87 (10)
C3—C4—C5—C10	−2.09 (16)	C14—C12—C13—O4	4.25 (17)
O2—C4—C5—C6	−1.00 (18)	C11—C12—C13—C1	1.35 (18)
C3—C4—C5—C6	178.17 (12)	C14—C12—C13—C1	−174.27 (11)
C10—C5—C6—C7	0.6 (2)	C2—C1—C13—O4	180.00 (10)
C4—C5—C6—C7	−179.67 (12)	C19—C1—C13—O4	−2.10 (17)
C5—C6—C7—C8	−0.1 (2)	C2—C1—C13—C12	−1.53 (18)
C6—C7—C8—C9	−0.6 (2)	C19—C1—C13—C12	176.37 (11)
C7—C8—C9—O3	−178.45 (13)	C13—C12—C14—C15	−119.77 (13)
C7—C8—C9—C10	0.8 (2)	C11—C12—C14—C15	64.81 (16)
C11—N1—C10—C5	1.65 (17)	C12—C14—C15—C16	−136.97 (13)
C11—N1—C10—C9	−178.35 (11)	C14—C15—C16—C17	−176.18 (13)
C6—C5—C10—N1	179.57 (11)	C14—C15—C16—C18	3.8 (2)
C4—C5—C10—N1	−0.18 (17)	C2—C1—C19—C20	−102.65 (13)
C6—C5—C10—C9	−0.43 (18)	C13—C1—C19—C20	79.52 (15)
C4—C5—C10—C9	179.82 (11)	C1—C19—C20—C21	−111.01 (15)
O3—C9—C10—N1	−0.96 (16)	C19—C20—C21—C23	2.4 (2)
C8—C9—C10—N1	179.75 (11)	C19—C20—C21—C22	179.80 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.915 (19)	1.699 (19)	2.5528 (13)	154.1 (17)
O3—H1O3···O2i	0.845 (19)	1.923 (19)	2.7501 (12)	165.9 (19)
N1—H1N1···O3	0.880 (18)	2.333 (18)	2.6893 (13)	104.3 (13)
C8—H8A···O2i	0.991 (19)	2.565 (18)	3.2918 (16)	130.1 (13)
C14—H14A···O4	0.969 (19)	2.254 (17)	2.7752 (16)	112.6 (12)
C19—H19A···O1	0.957 (16)	2.352 (15)	2.8197 (17)	109.6 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.915 (19)	1.699 (19)	2.5528 (13)	154.1 (17)
O3—H1O3⋯O2i	0.845 (19)	1.923 (19)	2.7501 (12)	165.9 (19)
N1—H1N1⋯O3	0.880 (18)	2.333 (18)	2.6893 (13)	104.3 (13)
C8—H8A⋯O2i	0.991 (19)	2.565 (18)	3.2918 (16)	130.1 (13)
C14—H14A⋯O4	0.969 (19)	2.254 (17)	2.7752 (16)	112.6 (12)
C19—H19A⋯O1	0.957 (16)	2.352 (15)	2.8197 (17)	109.6 (11)

Symmetry code: (i) .