(E)-1-{4-[Bis(4-meth-oxy-phen-yl)meth-yl]piperazin-1-yl}-3-(4-methyl-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(29)H(32)N(2)O(3), the piperazine ring has a chair conformation. The amide N atom is almost planar (bond angle sum = 359.5°), whereas the other N atom is clearly pyramidal (bond angle sum = 330.4°). The dihedral angle between the meth-oxy-benzene rings is 81.29 (16)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds.

Related literature

For structures and properties of cinnamic acid derivatives, see: Shi et al. (2005 ▶); Qian et al. (2010 ▶). For the synthesis, see: Wu et al. (2008 ▶). For related structures, see: Mouillé et al. (1975) ▶; Teng et al. (2011 ▶).

Experimental

Crystal data

C29H32N2O3

M = 456.57

Monoclinic,

a = 10.114 (2) Å

b = 11.867 (2) Å

c = 21.573 (4) Å

β = 97.12 (3)°

V = 2569.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

5002 measured reflections

4718 independent reflections

2269 reflections with I > 2σ(I)

R int = 0.037

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.189

S = 1.01

4718 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039353/hb6419sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039353/hb6419Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039353/hb6419Isup3.cml

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

C29H32N2O3	F(000) = 976
Mr = 456.57	Dx = 1.180 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.114 (2) Å	θ = 9–13°
b = 11.867 (2) Å	µ = 0.08 mm−1
c = 21.573 (4) Å	T = 293 K
β = 97.12 (3)°	Block, colorless
V = 2569.3 (9) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube	θmax = 25.4°, θmin = 1.9°
graphite	h = 0→12
ω/2θ scans	k = 0→14
5002 measured reflections	l = −25→25
4718 independent reflections	3 standard reflections every 200 reflections
2269 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.189	w = 1/[σ2(Fo2) + (0.090P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4718 reflections	Δρmax = 0.17 e Å−3
308 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (15)

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	−0.1506 (2)	0.6822 (2)	0.16861 (11)	0.0805 (7)
N1	0.3133 (2)	0.4580 (2)	0.35291 (12)	0.0619 (7)
C1	0.1571 (3)	0.5157 (3)	0.19907 (15)	0.0668 (9)
H1A	0.2051	0.4617	0.1800	0.080*
N2	0.3059 (3)	0.2833 (2)	0.44379 (13)	0.0758 (8)
O2	0.6891 (2)	0.8783 (2)	0.30391 (14)	0.1012 (9)
C2	0.0404 (3)	0.5583 (3)	0.16694 (15)	0.0685 (9)
H2A	0.0116	0.5337	0.1266	0.082*
O3	0.4449 (2)	0.15376 (19)	0.49261 (11)	0.0832 (7)
C3	−0.0322 (3)	0.6364 (3)	0.19481 (14)	0.0589 (8)
C4	0.0133 (3)	0.6732 (3)	0.25457 (15)	0.0667 (9)
H4A	−0.0355	0.7260	0.2741	0.080*
C5	0.1310 (3)	0.6317 (3)	0.28509 (14)	0.0638 (9)
H5A	0.1622	0.6587	0.3247	0.077*
C6	0.2032 (3)	0.5510 (2)	0.25791 (14)	0.0555 (8)
C7	−0.2053 (4)	0.6408 (4)	0.10938 (18)	0.1126 (15)
H7A	−0.2877	0.6788	0.0961	0.169*
H7B	−0.2213	0.5614	0.1122	0.169*
H7C	−0.1439	0.6542	0.0796	0.169*
C8	0.3347 (3)	0.5063 (3)	0.29208 (15)	0.0627 (9)
H8A	0.3674	0.4465	0.2666	0.075*
C9	0.4351 (3)	0.6013 (3)	0.29770 (15)	0.0607 (8)
C10	0.5010 (3)	0.6272 (3)	0.24752 (17)	0.0716 (9)
H10A	0.4877	0.5815	0.2123	0.086*
C11	0.5857 (3)	0.7177 (3)	0.24720 (19)	0.0786 (10)
H11A	0.6291	0.7321	0.2125	0.094*
C12	0.6056 (3)	0.7869 (3)	0.2986 (2)	0.0740 (10)
C13	0.5425 (4)	0.7637 (3)	0.35055 (18)	0.0772 (10)
H13A	0.5571	0.8091	0.3859	0.093*
C14	0.4574 (3)	0.6722 (3)	0.34940 (16)	0.0710 (9)
H14A	0.4139	0.6576	0.3841	0.085*
C15	0.7257 (4)	0.9251 (3)	0.2473 (2)	0.1188 (17)
H15A	0.7840	0.9881	0.2570	0.178*
H15B	0.6470	0.9496	0.2213	0.178*
H15C	0.7705	0.8689	0.2257	0.178*
C16	0.2141 (3)	0.3666 (3)	0.34414 (16)	0.0738 (10)
H16A	0.2478	0.3063	0.3201	0.089*
H16B	0.1326	0.3949	0.3208	0.089*
C17	0.4359 (3)	0.4114 (3)	0.38666 (16)	0.0709 (10)
H17A	0.5041	0.4693	0.3919	0.085*
H17B	0.4680	0.3502	0.3628	0.085*
C18	0.4094 (3)	0.3686 (3)	0.45001 (17)	0.0802 (10)
H18A	0.4906	0.3370	0.4718	0.096*
H18B	0.3822	0.4309	0.4746	0.096*
C19	0.1841 (3)	0.3211 (3)	0.40618 (18)	0.0801 (11)
H19A	0.1422	0.3794	0.4285	0.096*
H19B	0.1223	0.2585	0.3992	0.096*
C20	0.3342 (3)	0.1781 (3)	0.46539 (15)	0.0644 (9)
C21	0.2268 (3)	0.0911 (3)	0.45499 (14)	0.0664 (9)
H21A	0.1387	0.1139	0.4451	0.080*
C22	0.2550 (3)	−0.0172 (3)	0.45954 (13)	0.0627 (9)
H22A	0.3441	−0.0361	0.4703	0.075*
C23	0.1603 (3)	−0.1113 (3)	0.44938 (13)	0.0598 (8)
C24	0.2069 (4)	−0.2212 (3)	0.45818 (15)	0.0700 (9)
H24A	0.2973	−0.2338	0.4698	0.084*
C25	0.1216 (4)	−0.3106 (3)	0.44992 (16)	0.0783 (10)
H25A	0.1554	−0.3829	0.4571	0.094*
C26	−0.0126 (4)	−0.2975 (3)	0.43129 (16)	0.0758 (10)
C27	−0.0588 (4)	−0.1881 (4)	0.42178 (19)	0.0875 (11)
H27A	−0.1489	−0.1758	0.4090	0.105*
C28	0.0254 (4)	−0.0979 (3)	0.43089 (18)	0.0828 (11)
H28A	−0.0090	−0.0256	0.4245	0.099*
C29	−0.1073 (4)	−0.3960 (3)	0.4196 (2)	0.1091 (14)
H29A	−0.0593	−0.4651	0.4284	0.164*
H29B	−0.1463	−0.3956	0.3767	0.164*
H29C	−0.1763	−0.3898	0.4462	0.164*

	U11	U22	U33	U12	U13	U23
O1	0.0657 (15)	0.1064 (19)	0.0666 (15)	0.0123 (13)	−0.0028 (12)	0.0018 (13)
N1	0.0574 (15)	0.0505 (15)	0.0751 (19)	−0.0007 (13)	−0.0018 (13)	0.0095 (13)
C1	0.064 (2)	0.071 (2)	0.066 (2)	0.0023 (17)	0.0119 (17)	−0.0140 (17)
N2	0.0694 (18)	0.0615 (19)	0.091 (2)	−0.0016 (15)	−0.0121 (15)	0.0209 (15)
O2	0.0820 (18)	0.0766 (18)	0.142 (3)	−0.0202 (15)	0.0005 (16)	0.0127 (17)
C2	0.070 (2)	0.081 (2)	0.054 (2)	−0.0048 (19)	0.0091 (17)	−0.0109 (18)
O3	0.0748 (16)	0.0746 (16)	0.0935 (18)	0.0067 (13)	−0.0159 (14)	0.0169 (13)
C3	0.0573 (19)	0.069 (2)	0.0500 (19)	−0.0021 (17)	0.0072 (15)	0.0069 (16)
C4	0.069 (2)	0.075 (2)	0.056 (2)	0.0135 (18)	0.0081 (17)	−0.0032 (17)
C5	0.072 (2)	0.068 (2)	0.0492 (18)	0.0056 (18)	0.0014 (16)	−0.0064 (16)
C6	0.0589 (19)	0.0534 (18)	0.0545 (19)	−0.0033 (15)	0.0083 (15)	−0.0008 (15)
C7	0.082 (3)	0.178 (5)	0.071 (3)	0.013 (3)	−0.019 (2)	−0.003 (3)
C8	0.062 (2)	0.0521 (18)	0.074 (2)	0.0035 (16)	0.0099 (17)	−0.0032 (16)
C9	0.0533 (18)	0.058 (2)	0.071 (2)	0.0066 (16)	0.0072 (16)	0.0023 (17)
C10	0.062 (2)	0.070 (2)	0.086 (2)	0.0013 (18)	0.0222 (19)	−0.0059 (19)
C11	0.063 (2)	0.074 (2)	0.103 (3)	0.003 (2)	0.028 (2)	0.006 (2)
C12	0.052 (2)	0.059 (2)	0.110 (3)	−0.0011 (17)	0.005 (2)	0.016 (2)
C13	0.085 (2)	0.060 (2)	0.083 (3)	−0.004 (2)	−0.004 (2)	−0.0008 (19)
C14	0.075 (2)	0.065 (2)	0.073 (2)	−0.0015 (19)	0.0083 (18)	0.0036 (18)
C15	0.107 (3)	0.074 (3)	0.185 (5)	−0.013 (2)	0.058 (3)	0.019 (3)
C16	0.063 (2)	0.060 (2)	0.094 (3)	−0.0029 (17)	−0.0091 (18)	0.0113 (19)
C17	0.058 (2)	0.058 (2)	0.093 (3)	−0.0010 (16)	−0.0062 (18)	0.0048 (18)
C18	0.080 (2)	0.067 (2)	0.087 (3)	−0.0058 (19)	−0.0167 (19)	0.011 (2)
C19	0.066 (2)	0.068 (2)	0.104 (3)	0.0004 (18)	−0.002 (2)	0.029 (2)
C20	0.071 (2)	0.061 (2)	0.061 (2)	0.0073 (19)	0.0064 (18)	0.0068 (16)
C21	0.066 (2)	0.063 (2)	0.071 (2)	0.0108 (18)	0.0084 (17)	0.0160 (17)
C22	0.071 (2)	0.061 (2)	0.056 (2)	0.0088 (18)	0.0078 (16)	0.0108 (16)
C23	0.068 (2)	0.061 (2)	0.0508 (18)	0.0069 (18)	0.0082 (15)	0.0097 (15)
C24	0.079 (2)	0.063 (2)	0.066 (2)	0.009 (2)	0.0013 (18)	−0.0006 (17)
C25	0.099 (3)	0.062 (2)	0.071 (2)	0.008 (2)	−0.004 (2)	−0.0009 (17)
C26	0.097 (3)	0.069 (2)	0.062 (2)	−0.012 (2)	0.012 (2)	−0.0043 (18)
C27	0.066 (2)	0.089 (3)	0.107 (3)	0.000 (2)	0.010 (2)	0.003 (2)
C28	0.074 (2)	0.063 (2)	0.110 (3)	0.008 (2)	0.005 (2)	0.017 (2)
C29	0.121 (3)	0.097 (3)	0.109 (3)	−0.023 (3)	0.014 (3)	−0.006 (3)

O1—C3	1.372 (3)	C13—H13A	0.9300
O1—C7	1.416 (4)	C14—H14A	0.9300
N1—C17	1.466 (4)	C15—H15A	0.9600
N1—C8	1.472 (4)	C15—H15B	0.9600
N1—C16	1.474 (4)	C15—H15C	0.9600
C1—C6	1.363 (4)	C16—C19	1.508 (4)
C1—C2	1.388 (4)	C16—H16A	0.9700
C1—H1A	0.9300	C16—H16B	0.9700
N2—C20	1.351 (4)	C17—C18	1.513 (4)
N2—C18	1.450 (4)	C17—H17A	0.9700
N2—C19	1.460 (4)	C17—H17B	0.9700
O2—C12	1.371 (4)	C18—H18A	0.9700
O2—C15	1.431 (5)	C18—H18B	0.9700
C2—C3	1.367 (4)	C19—H19A	0.9700
C2—H2A	0.9300	C19—H19B	0.9700
O3—C20	1.232 (4)	C20—C21	1.495 (4)
C3—C4	1.385 (4)	C21—C22	1.318 (4)
C4—C5	1.377 (4)	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.470 (4)
C5—C6	1.379 (4)	C22—H22A	0.9300
C5—H5A	0.9300	C23—C28	1.382 (4)
C6—C8	1.533 (4)	C23—C24	1.392 (4)
C7—H7A	0.9600	C24—C25	1.365 (4)
C7—H7B	0.9600	C24—H24A	0.9300
C7—H7C	0.9600	C25—C26	1.375 (5)
C8—C9	1.513 (4)	C25—H25A	0.9300
C8—H8A	0.9800	C26—C27	1.387 (5)
C9—C10	1.374 (4)	C26—C29	1.512 (5)
C9—C14	1.393 (4)	C27—C28	1.366 (5)
C10—C11	1.375 (4)	C27—H27A	0.9300
C10—H10A	0.9300	C28—H28A	0.9300
C11—C12	1.374 (5)	C29—H29A	0.9600
C11—H11A	0.9300	C29—H29B	0.9600
C12—C13	1.385 (5)	C29—H29C	0.9600
C13—C14	1.383 (4)
C3—O1—C7	117.2 (3)	H15A—C15—H15C	109.5
C17—N1—C8	112.4 (2)	H15B—C15—H15C	109.5
C17—N1—C16	107.9 (2)	N1—C16—C19	111.0 (3)
C8—N1—C16	110.2 (2)	N1—C16—H16A	109.4
C6—C1—C2	121.6 (3)	C19—C16—H16A	109.4
C6—C1—H1A	119.2	N1—C16—H16B	109.4
C2—C1—H1A	119.2	C19—C16—H16B	109.4
C20—N2—C18	119.6 (3)	H16A—C16—H16B	108.0
C20—N2—C19	127.2 (3)	N1—C17—C18	109.9 (3)
C18—N2—C19	112.7 (3)	N1—C17—H17A	109.7
C12—O2—C15	117.2 (3)	C18—C17—H17A	109.7
C3—C2—C1	119.8 (3)	N1—C17—H17B	109.7
C3—C2—H2A	120.1	C18—C17—H17B	109.7
C1—C2—H2A	120.1	H17A—C17—H17B	108.2
C2—C3—O1	125.2 (3)	N2—C18—C17	111.0 (3)
C2—C3—C4	119.3 (3)	N2—C18—H18A	109.4
O1—C3—C4	115.5 (3)	C17—C18—H18A	109.4
C5—C4—C3	120.0 (3)	N2—C18—H18B	109.4
C5—C4—H4A	120.0	C17—C18—H18B	109.4
C3—C4—H4A	120.0	H18A—C18—H18B	108.0
C4—C5—C6	121.1 (3)	N2—C19—C16	110.8 (3)
C4—C5—H5A	119.4	N2—C19—H19A	109.5
C6—C5—H5A	119.4	C16—C19—H19A	109.5
C1—C6—C5	118.1 (3)	N2—C19—H19B	109.5
C1—C6—C8	121.2 (3)	C16—C19—H19B	109.5
C5—C6—C8	120.6 (3)	H19A—C19—H19B	108.1
O1—C7—H7A	109.5	O3—C20—N2	121.5 (3)
O1—C7—H7B	109.5	O3—C20—C21	120.7 (3)
H7A—C7—H7B	109.5	N2—C20—C21	117.8 (3)
O1—C7—H7C	109.5	C22—C21—C20	121.0 (3)
H7A—C7—H7C	109.5	C22—C21—H21A	119.5
H7B—C7—H7C	109.5	C20—C21—H21A	119.5
N1—C8—C9	113.0 (2)	C21—C22—C23	126.8 (3)
N1—C8—C6	110.4 (2)	C21—C22—H22A	116.6
C9—C8—C6	108.3 (2)	C23—C22—H22A	116.6
N1—C8—H8A	108.3	C28—C23—C24	116.9 (3)
C9—C8—H8A	108.3	C28—C23—C22	123.9 (3)
C6—C8—H8A	108.3	C24—C23—C22	119.2 (3)
C10—C9—C14	116.7 (3)	C25—C24—C23	120.8 (3)
C10—C9—C8	119.3 (3)	C25—C24—H24A	119.6
C14—C9—C8	123.7 (3)	C23—C24—H24A	119.6
C9—C10—C11	122.8 (3)	C24—C25—C26	122.4 (3)
C9—C10—H10A	118.6	C24—C25—H25A	118.8
C11—C10—H10A	118.6	C26—C25—H25A	118.8
C12—C11—C10	119.5 (3)	C25—C26—C27	116.8 (3)
C12—C11—H11A	120.3	C25—C26—C29	122.9 (4)
C10—C11—H11A	120.3	C27—C26—C29	120.2 (4)
O2—C12—C11	124.6 (4)	C28—C27—C26	121.3 (3)
O2—C12—C13	115.5 (4)	C28—C27—H27A	119.4
C11—C12—C13	119.9 (3)	C26—C27—H27A	119.4
C14—C13—C12	119.3 (3)	C27—C28—C23	121.8 (3)
C14—C13—H13A	120.3	C27—C28—H28A	119.1
C12—C13—H13A	120.3	C23—C28—H28A	119.1
C13—C14—C9	121.8 (3)	C26—C29—H29A	109.5
C13—C14—H14A	119.1	C26—C29—H29B	109.5
C9—C14—H14A	119.1	H29A—C29—H29B	109.5
O2—C15—H15A	109.5	C26—C29—H29C	109.5
O2—C15—H15B	109.5	H29A—C29—H29C	109.5
H15A—C15—H15B	109.5	H29B—C29—H29C	109.5
O2—C15—H15C	109.5
C6—C1—C2—C3	−1.0 (5)	C12—C13—C14—C9	1.2 (5)
C1—C2—C3—O1	−178.1 (3)	C10—C9—C14—C13	−0.5 (5)
C1—C2—C3—C4	1.0 (5)	C8—C9—C14—C13	−174.8 (3)
C7—O1—C3—C2	3.5 (5)	C17—N1—C16—C19	60.7 (3)
C7—O1—C3—C4	−175.6 (3)	C8—N1—C16—C19	−176.3 (2)
C2—C3—C4—C5	0.5 (5)	C8—N1—C17—C18	177.1 (3)
O1—C3—C4—C5	179.6 (3)	C16—N1—C17—C18	−61.3 (3)
C3—C4—C5—C6	−2.0 (5)	C20—N2—C18—C17	118.8 (3)
C2—C1—C6—C5	−0.5 (5)	C19—N2—C18—C17	−53.6 (4)
C2—C1—C6—C8	−177.9 (3)	N1—C17—C18—N2	58.3 (4)
C4—C5—C6—C1	2.0 (5)	C20—N2—C19—C16	−119.4 (4)
C4—C5—C6—C8	179.4 (3)	C18—N2—C19—C16	52.4 (4)
C17—N1—C8—C9	−60.0 (3)	N1—C16—C19—N2	−56.1 (4)
C16—N1—C8—C9	179.7 (2)	C18—N2—C20—O3	2.9 (5)
C17—N1—C8—C6	178.5 (2)	C19—N2—C20—O3	174.1 (3)
C16—N1—C8—C6	58.2 (3)	C18—N2—C20—C21	−176.8 (3)
C1—C6—C8—N1	−124.9 (3)	C19—N2—C20—C21	−5.6 (5)
C5—C6—C8—N1	57.7 (4)	O3—C20—C21—C22	−17.6 (5)
C1—C6—C8—C9	110.9 (3)	N2—C20—C21—C22	162.1 (3)
C5—C6—C8—C9	−66.4 (4)	C20—C21—C22—C23	−178.7 (3)
N1—C8—C9—C10	156.6 (3)	C21—C22—C23—C28	2.5 (5)
C6—C8—C9—C10	−80.7 (3)	C21—C22—C23—C24	−177.9 (3)
N1—C8—C9—C14	−29.2 (4)	C28—C23—C24—C25	−1.2 (5)
C6—C8—C9—C14	93.4 (4)	C22—C23—C24—C25	179.2 (3)
C14—C9—C10—C11	0.2 (5)	C23—C24—C25—C26	1.6 (5)
C8—C9—C10—C11	174.7 (3)	C24—C25—C26—C27	−0.7 (5)
C9—C10—C11—C12	−0.6 (5)	C24—C25—C26—C29	177.6 (3)
C15—O2—C12—C11	19.9 (5)	C25—C26—C27—C28	−0.3 (5)
C15—O2—C12—C13	−162.4 (3)	C29—C26—C27—C28	−178.7 (4)
C10—C11—C12—O2	178.9 (3)	C26—C27—C28—C23	0.6 (6)
C10—C11—C12—C13	1.3 (5)	C24—C23—C28—C27	0.2 (5)
O2—C12—C13—C14	−179.4 (3)	C22—C23—C28—C27	179.7 (3)
C11—C12—C13—C14	−1.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.60	3.360 (4)	140
C22—H22A···O3ii	0.93	2.59	3.483 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.60	3.360 (4)	140
C22—H22A⋯O3ii	0.93	2.59	3.483 (4)	160

Symmetry codes: (i) ; (ii) .