5'-Allyl-2'-benzoyloxy-3'-methoxy-4-nitroazobenzene

The structure of the title compound, 4-allyl-2-methoxy-6-[(4-nitrophenyl)diazenyl]phenyl benzoate, C₂₃H₁₉N₃O₅, displays the characteristic features of azobenzene derivatives. The azobenzene moiety of the molecule has a trans configuration and in this moiety, average C-N and N=N bond lengths are 1.441 (3) and 1.241 (3) Å, respectively.

S1. Comment

The crystal and molecular structures of the title compound, (I), were investigated in order to determine the conformation, crystal packing and also to confirm the stereochemistry. In the molecule, bond lengths and angles are very similar to the structures of azo compounds studied previously (Işık et al., 1997; Işık, Aygün, Kocaokutgen, Tahir et al., 1998; Işık, Aygün, Kocaokutgen & Tahir, 1998).

The numbering scheme and a displacement ellipsoid plot of (I) are shown in Fig. 1. In the azo frame, the average C—N bond length is 1.441 (3) Å, that indicates the single-bond character. The C—NO₂ bond length is 1.479 (4) Å, which is similar to the observed values in the literature (Zhu et al., 1996; Zhang et al., 1998). The N2=N3 bond length of 1.241 (3) Å is typical for a double bond. The angles C4—N2—N3 and N2—N3—C7 are 114.0 (2) and 113.7 (2)°, respectively. The torsion angles about the C—N bond [N3—N2—C4—C3 = 178.9 (2) and N3—N2—C4—C5 = −1.9 (4)°] are comparable with trans azo compounds. The three phenyl rings are planar within experimental error and the largest deviation of −0.010 (2) Å is at the C18 atom of the C14—C19 ring. While the twist angle of the nitro group relative to the phenyl ring is 3.7 (1)°, C1—C6 and C7—C12 rings in the azobenzene frame are twisted by 1.83 (2) and 1.68 (2)° out of the azo group plane, respectively. These results show that the azo group moiety is almost planar. The C7—C12 ring and the other groups those are adjacent to the C7—C12 ring, except the methoxy group, are not coplanar. Also, dihedral angles between the C14—C19 ring and the C1—C6, and C7—C12 rings are 97.7 (1) and 96.2 (1)°, respectively.

The compound has four intramolecular C—H···O contacts. Two of these are C2—H2B···O1 and C6—H6A···O2 which maintain the coplanarity of the phenyl ring and the nitro group. The other two intramolecular hydrogen bonds, C15—H15A···O5 and C19—H19A···O4, are located between the unsubstituted phenyl ring and the benzoyloxy group. Also, the crystal packing involves two C—H···O intermolecular hydrogen bonds. Details of these interactions are shown in Table 2.

Displacement parameters of C20, C21 and C22 atoms of the allyl group are larger than other atoms. This behaviour may be due to considerable freedom of movement of the group in the crystal. Also, this accounts for the apparent shortening of the C21—C22 bond length [1.245 (5) Å].

S2. Experimental

5'-Allyl-2'-hydroxy-3'-methoxy-4-nitroazobenzene (1 g, 3.19 mmol) was dissolved in NaoH (1M, 100 ml) by heating. After cooling the solution, benzoyl chloride was added, and the mixture was refluxed for 1 h. After cooling, a precipitate was obtained when Na₂O₃ (1 g, 9.43 mmol) was added. The precipitate was washed with pure water, filtered and dried. Diffraction-quality crystals were obtained by recrystallization from ethyl acetate (m.p. 428–434 K). ¹H NMR (CDCl₃): δ 8.5–7.0 (m, Aromatic), 6.2–5.8 (m, –CH=), 5.4–5.1 (m, =CH₂), 3.9 (s,-CH₃), 3.6–3.4 (s,-CH₂); ¹³C-NMR (CDCl³):δ 170 (C=O), 145–120 (Aromatic), 140–130 (–CH=), 116–112 (=CH₂), 54.3 (–OCH₃), 40–10 (–CH₂); IR (cm⁻¹): 3080–2800 (CH₂, CH), 1635 (Allyl, C=C), 1450–1400 (N=N), 1600–1450 (C₆H₅), 1385 (OCH₃), 1740 (C=O); UV[λ(nm), ε (mol⁻¹cm⁻¹)]: 271.1 (6268.1), 241.4 (9664.8), 206.2 (1229.05); analysis calculated for C₂₃H₁₉N₃O₅ (%): C 68.18, H 4.55, N 10.07; Found (%): C 68.19, H 4.62, N 10.02.

S3. Refinement

All H atoms were located geometrically 0.93 Å from the parent C atoms except for the C20 and methyl-H atoms which were located 0.97 and 0.96 Å, respectively. A riding model was used for all H atoms with an isotropic displacement parameter 1.5 (for methyl-H atoms) or 1.2 (for the other H atoms) times the value of the equivalent isotropic displacemnt parameter of the carrier atom.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXTL and PARST (Nardelli, 1995).

Figures

Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and atom-numbering scheme. Fig. 2. Packing along [100] for (I). Dashed lines indicate C—H···O interactions.

(I)

Crystal data

C23H19N3O5	F(000) = 872
Mr = 417.41	Dx = 1.286 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7564 (1) Å	Cell parameters from 4481 reflections
b = 22.3441 (5) Å	θ = 1.5–33°
c = 12.5552 (2) Å	µ = 0.09 mm^−1
β = 97.766 (1)°	T = 293 K
V = 2155.98 (7) Å^3	Slab, light yellow
Z = 4	0.32 × 0.24 × 0.08 mm

Data collection

Siemens SMART CCD area detector diffractometer	1920 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
ω scans	h = −10→8
15921 measured reflections	k = −14→29
5166 independent reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.197	w = 1/[σ^2(Fo^2) + (0.0819P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
5166 reflections	Δρmax = 0.24 e Å^−3
281 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (11)

Special details

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.

The data collection was covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 3 cm and the detector swing angle was −35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating thirty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. The structure was solved by direct methods and refined by full-matrix least-square techniques.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9882 (4)	0.15459 (13)	−0.0585 (3)	0.1368 (11)
O2	0.9476 (4)	0.07217 (15)	0.0203 (3)	0.1467 (12)
O3	−0.2560 (2)	0.17466 (9)	0.37821 (16)	0.0800 (6)
O4	0.0105 (2)	0.12748 (8)	0.29568 (15)	0.0672 (5)
O5	0.1935 (3)	0.14157 (9)	0.44743 (17)	0.0857 (7)
N1	0.9096 (4)	0.12358 (16)	−0.0020 (3)	0.0999 (9)
N2	0.3269 (3)	0.22698 (11)	0.14856 (19)	0.0737 (7)
N3	0.2361 (3)	0.19428 (10)	0.19837 (19)	0.0684 (6)
C1	0.7564 (4)	0.14978 (14)	0.0392 (2)	0.0706 (8)
C2	0.7162 (4)	0.20842 (14)	0.0180 (2)	0.0725 (8)
H2B	0.7841	0.2317	−0.0215	0.087*
C3	0.5737 (4)	0.23221 (13)	0.0562 (2)	0.0693 (8)
H3B	0.5448	0.2722	0.0435	0.083*
C4	0.4734 (3)	0.19698 (13)	0.1131 (2)	0.0642 (7)
C5	0.5164 (4)	0.13759 (13)	0.1341 (2)	0.0768 (8)
H5A	0.4480	0.1140	0.1729	0.092*
C6	0.6596 (4)	0.11378 (13)	0.0976 (2)	0.0812 (9)
H6A	0.6911	0.0741	0.1118	0.097*
C7	0.0905 (3)	0.22464 (12)	0.2342 (2)	0.0622 (7)
C8	0.0532 (4)	0.28463 (13)	0.2188 (2)	0.0717 (8)
H8A	0.1265	0.3085	0.1840	0.086*
C9	−0.0911 (4)	0.30969 (13)	0.2542 (2)	0.0739 (8)
C10	−0.1966 (4)	0.27341 (14)	0.3085 (2)	0.0726 (8)
H10A	−0.2930	0.2900	0.3341	0.087*
C11	−0.1614 (4)	0.21360 (13)	0.3252 (2)	0.0655 (7)
C12	−0.0169 (3)	0.18897 (12)	0.2867 (2)	0.0606 (7)
C13	0.1219 (4)	0.10782 (12)	0.3815 (2)	0.0637 (7)
C14	0.1395 (3)	0.04205 (12)	0.3816 (3)	0.0662 (8)
C15	0.2212 (4)	0.01497 (14)	0.4741 (3)	0.0872 (10)
H15A	0.2692	0.0384	0.5319	0.105*
C16	0.2320 (5)	−0.04649 (16)	0.4812 (4)	0.1039 (11)
H16A	0.2859	−0.0645	0.5437	0.125*
C17	0.1632 (5)	−0.08085 (16)	0.3958 (4)	0.1032 (12)
H17A	0.1689	−0.1223	0.4010	0.124*
C18	0.0860 (5)	−0.05493 (16)	0.3028 (4)	0.1005 (11)
H18A	0.0428	−0.0788	0.2445	0.121*
C19	0.0719 (4)	0.00697 (14)	0.2953 (3)	0.0815 (9)
H19A	0.0173	0.0247	0.2326	0.098*
C20	−0.1345 (5)	0.37473 (15)	0.2338 (3)	0.1015 (11)
H20A	−0.0795	0.3880	0.1730	0.122*
H20B	−0.2593	0.3784	0.2138	0.122*
C21	−0.0827 (7)	0.41336 (19)	0.3218 (4)	0.1466 (19)
H21A	−0.1225	0.4008	0.3848	0.176*
C22	0.0042 (7)	0.4603 (2)	0.3338 (5)	0.185 (3)
H22A	0.0504	0.4769	0.2758	0.222*
H22B	0.0229	0.4788	0.4007	0.222*
C23	−0.4073 (4)	0.19738 (15)	0.4184 (3)	0.0865 (10)
H23A	−0.4616	0.1658	0.4536	0.130*
H23B	−0.4877	0.2125	0.3597	0.130*
H23C	−0.3741	0.2290	0.4687	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.137 (2)	0.125 (2)	0.169 (3)	−0.0211 (18)	0.095 (2)	−0.0158 (19)
O2	0.150 (2)	0.117 (2)	0.192 (3)	0.0325 (19)	0.089 (2)	0.010 (2)
O3	0.0746 (13)	0.0879 (14)	0.0814 (16)	0.0020 (11)	0.0246 (11)	0.0038 (12)
O4	0.0695 (11)	0.0648 (12)	0.0672 (13)	−0.0041 (9)	0.0094 (10)	−0.0044 (10)
O5	0.1033 (15)	0.0669 (12)	0.0811 (16)	0.0004 (11)	−0.0089 (12)	−0.0086 (11)
N1	0.101 (2)	0.101 (2)	0.104 (3)	−0.009 (2)	0.0395 (18)	−0.020 (2)
N2	0.0755 (15)	0.0805 (16)	0.0652 (17)	−0.0032 (14)	0.0099 (13)	0.0115 (13)
N3	0.0721 (15)	0.0741 (15)	0.0598 (15)	−0.0029 (13)	0.0117 (12)	0.0020 (13)
C1	0.0734 (19)	0.078 (2)	0.062 (2)	−0.0125 (16)	0.0155 (15)	−0.0109 (16)
C2	0.0724 (19)	0.087 (2)	0.059 (2)	−0.0156 (17)	0.0119 (15)	0.0052 (16)
C3	0.0750 (19)	0.0707 (18)	0.062 (2)	−0.0079 (16)	0.0086 (15)	0.0091 (15)
C4	0.0660 (18)	0.0705 (18)	0.0554 (19)	−0.0017 (15)	0.0059 (14)	0.0005 (14)
C5	0.081 (2)	0.074 (2)	0.079 (2)	−0.0130 (16)	0.0259 (16)	0.0024 (17)
C6	0.088 (2)	0.0702 (19)	0.090 (2)	−0.0021 (17)	0.0284 (18)	−0.0021 (17)
C7	0.0631 (16)	0.0681 (18)	0.0546 (18)	−0.0005 (14)	0.0054 (14)	0.0006 (14)
C8	0.076 (2)	0.0718 (19)	0.066 (2)	0.0003 (16)	0.0053 (15)	0.0111 (15)
C9	0.087 (2)	0.0713 (19)	0.060 (2)	0.0105 (17)	−0.0021 (16)	0.0076 (16)
C10	0.0692 (18)	0.085 (2)	0.062 (2)	0.0134 (16)	0.0029 (15)	−0.0009 (16)
C11	0.0678 (18)	0.0755 (19)	0.0525 (18)	0.0017 (16)	0.0057 (14)	−0.0012 (15)
C12	0.0667 (17)	0.0597 (17)	0.0546 (18)	0.0031 (14)	0.0049 (13)	−0.0012 (14)
C13	0.0677 (18)	0.0630 (17)	0.063 (2)	−0.0024 (14)	0.0185 (15)	−0.0024 (15)
C14	0.0644 (17)	0.0631 (17)	0.075 (2)	−0.0008 (14)	0.0223 (15)	−0.0093 (16)
C15	0.103 (2)	0.070 (2)	0.090 (3)	0.0054 (18)	0.0164 (19)	−0.0001 (18)
C16	0.122 (3)	0.072 (2)	0.121 (3)	0.018 (2)	0.028 (2)	0.008 (2)
C17	0.109 (3)	0.062 (2)	0.148 (4)	0.004 (2)	0.053 (3)	−0.008 (2)
C18	0.100 (3)	0.078 (2)	0.129 (4)	−0.010 (2)	0.036 (2)	−0.030 (2)
C19	0.081 (2)	0.073 (2)	0.094 (3)	−0.0017 (16)	0.0245 (17)	−0.0154 (18)
C20	0.118 (3)	0.091 (2)	0.094 (3)	0.032 (2)	0.009 (2)	0.009 (2)
C21	0.200 (5)	0.080 (3)	0.149 (4)	0.040 (3)	−0.017 (4)	0.009 (3)
C22	0.229 (6)	0.094 (3)	0.224 (6)	0.035 (3)	−0.001 (5)	−0.011 (4)
C23	0.0660 (18)	0.119 (3)	0.078 (2)	0.0084 (18)	0.0208 (16)	0.0013 (19)

Geometric parameters (Å, º)

O1—N1	1.213 (3)	C9—C20	1.506 (4)
O2—N1	1.209 (4)	C10—C11	1.374 (4)
O3—C11	1.368 (3)	C10—H10A	0.9300
O3—C23	1.432 (3)	C11—C12	1.392 (4)
O4—C13	1.359 (3)	C13—C14	1.476 (4)
O4—C12	1.393 (3)	C14—C19	1.382 (4)
O5—C13	1.200 (3)	C14—C15	1.385 (4)
N1—C1	1.479 (4)	C15—C16	1.378 (4)
N2—N3	1.241 (3)	C15—H15A	0.9300
N2—C4	1.440 (3)	C16—C17	1.367 (5)
N3—C7	1.441 (3)	C16—H16A	0.9300
C1—C2	1.365 (4)	C17—C18	1.367 (5)
C1—C6	1.377 (4)	C17—H17A	0.9300
C2—C3	1.371 (4)	C18—C19	1.390 (4)
C2—H2B	0.9300	C18—H18A	0.9300
C3—C4	1.373 (4)	C19—H19A	0.9300
C3—H3B	0.9300	C20—C21	1.417 (5)
C4—C5	1.385 (4)	C20—H20A	0.9700
C5—C6	1.366 (4)	C20—H20B	0.9700
C5—H5A	0.9300	C21—C22	1.245 (5)
C6—H6A	0.9300	C21—H21A	0.9300
C7—C8	1.379 (4)	C22—H22A	0.9300
C7—C12	1.383 (3)	C22—H22B	0.9300
C8—C9	1.378 (4)	C23—H23A	0.9600
C8—H8A	0.9300	C23—H23B	0.9600
C9—C10	1.394 (4)	C23—H23C	0.9600
C11—O3—C23	117.7 (2)	C7—C12—O4	120.8 (2)
C13—O4—C12	117.2 (2)	C11—C12—O4	118.9 (2)
O2—N1—O1	123.5 (3)	O5—C13—O4	122.0 (3)
O2—N1—C1	118.5 (3)	O5—C13—C14	126.2 (3)
O1—N1—C1	118.0 (3)	O4—C13—C14	111.8 (3)
N3—N2—C4	114.0 (2)	C19—C14—C15	119.5 (3)
N2—N3—C7	113.7 (2)	C19—C14—C13	122.6 (3)
C2—C1—C6	122.5 (3)	C15—C14—C13	117.9 (3)
C2—C1—N1	119.0 (3)	C16—C15—C14	120.4 (3)
C6—C1—N1	118.4 (3)	C16—C15—H15A	119.8
C1—C2—C3	118.6 (3)	C14—C15—H15A	119.8
C1—C2—H2B	120.7	C17—C16—C15	119.7 (4)
C3—C2—H2B	120.7	C17—C16—H16A	120.1
C2—C3—C4	120.0 (3)	C15—C16—H16A	120.1
C2—C3—H3B	120.0	C16—C17—C18	120.8 (3)
C4—C3—H3B	120.0	C16—C17—H17A	119.6
C3—C4—C5	120.7 (3)	C18—C17—H17A	119.6
C3—C4—N2	114.8 (3)	C17—C18—C19	120.1 (4)
C5—C4—N2	124.5 (3)	C17—C18—H18A	120.0
C6—C5—C4	119.7 (3)	C19—C18—H18A	120.0
C6—C5—H5A	120.2	C14—C19—C18	119.5 (3)
C4—C5—H5A	120.2	C14—C19—H19A	120.2
C5—C6—C1	118.5 (3)	C18—C19—H19A	120.2
C5—C6—H6A	120.7	C21—C20—C9	114.9 (3)
C1—C6—H6A	120.7	C21—C20—H20A	108.5
C8—C7—C12	119.9 (3)	C9—C20—H20A	108.5
C8—C7—N3	124.9 (3)	C21—C20—H20B	108.5
C12—C7—N3	115.2 (2)	C9—C20—H20B	108.5
C9—C8—C7	120.9 (3)	H20A—C20—H20B	107.5
C9—C8—H8A	119.5	C22—C21—C20	134.4 (6)
C7—C8—H8A	119.5	C22—C21—H21A	112.8
C8—C9—C10	118.5 (3)	C20—C21—H21A	112.8
C8—C9—C20	120.7 (3)	C21—C22—H22A	120.0
C10—C9—C20	120.8 (3)	C21—C22—H22B	120.0
C11—C10—C9	121.5 (3)	H22A—C22—H22B	120.0
C11—C10—H10A	119.3	O3—C23—H23A	109.5
C9—C10—H10A	119.3	O3—C23—H23B	109.5
O3—C11—C10	125.7 (3)	H23A—C23—H23B	109.5
O3—C11—C12	115.3 (2)	O3—C23—H23C	109.5
C10—C11—C12	119.0 (3)	H23A—C23—H23C	109.5
C7—C12—C11	120.2 (2)	H23B—C23—H23C	109.5
C4—N2—N3—C7	179.6 (2)	C9—C10—C11—C12	0.0 (4)
O2—N1—C1—C2	177.5 (3)	C8—C7—C12—C11	−0.8 (4)
O1—N1—C1—C2	−4.1 (4)	N3—C7—C12—C11	179.8 (2)
O2—N1—C1—C6	−2.5 (5)	C8—C7—C12—O4	174.9 (2)
O1—N1—C1—C6	175.8 (3)	N3—C7—C12—O4	−4.5 (3)
C6—C1—C2—C3	−0.2 (4)	O3—C11—C12—C7	−178.4 (2)
N1—C1—C2—C3	179.7 (2)	C10—C11—C12—C7	1.1 (4)
C1—C2—C3—C4	−0.9 (4)	O3—C11—C12—O4	5.8 (3)
C2—C3—C4—C5	1.0 (4)	C10—C11—C12—O4	−174.7 (2)
C2—C3—C4—N2	−179.8 (2)	C13—O4—C12—C7	87.8 (3)
N3—N2—C4—C3	178.9 (2)	C13—O4—C12—C11	−96.5 (3)
N3—N2—C4—C5	−1.9 (4)	C12—O4—C13—O5	0.4 (4)
C3—C4—C5—C6	−0.1 (4)	C12—O4—C13—C14	180.0 (2)
N2—C4—C5—C6	−179.3 (2)	O5—C13—C14—C19	−170.8 (3)
C4—C5—C6—C1	−0.9 (4)	O4—C13—C14—C19	9.7 (4)
C2—C1—C6—C5	1.0 (4)	O5—C13—C14—C15	11.8 (4)
N1—C1—C6—C5	−178.9 (3)	O4—C13—C14—C15	−167.7 (2)
N2—N3—C7—C8	−1.6 (4)	C19—C14—C15—C16	−1.4 (4)
N2—N3—C7—C12	177.8 (2)	C13—C14—C15—C16	176.1 (3)
C12—C7—C8—C9	−0.6 (4)	C14—C15—C16—C17	0.7 (5)
N3—C7—C8—C9	178.8 (2)	C15—C16—C17—C18	1.0 (5)
C7—C8—C9—C10	1.6 (4)	C16—C17—C18—C19	−2.0 (5)
C7—C8—C9—C20	−177.9 (3)	C15—C14—C19—C18	0.4 (4)
C8—C9—C10—C11	−1.3 (4)	C13—C14—C19—C18	−176.9 (3)
C20—C9—C10—C11	178.2 (3)	C17—C18—C19—C14	1.3 (5)
C23—O3—C11—C10	1.3 (4)	C8—C9—C20—C21	−99.4 (4)
C23—O3—C11—C12	−179.2 (2)	C10—C9—C20—C21	81.2 (4)
C9—C10—C11—O3	179.4 (2)	C9—C20—C21—C22	127.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1	0.93	2.43	2.712 (3)	98
C6—H6A···O2	0.93	2.43	2.715 (3)	98
C15—H15A···O5	0.93	2.57	2.854 (1)	98
C19—H19A···O4	0.93	2.43	2.735 (1)	99
C16—H16A···O3^i	0.93	2.67	3.356 (2)	131
C23—H23A···O5^ii	0.96	2.72	3.400 (4)	129

Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z.