5-Nitro-1,3-bis-(prop-2-yn-yl)-1H-1,3-benzimidazol-2(3H)-one.

The title compound, C13H9N3O3, crystallizes with two identical but differently oriented mol-ecules in the asymmetric unit, the dihedral angle between the fused-ring systems of the two molecules being 64.39 (7)°. The two prop-2-ynyl chains are located on opposite sides of the mol-ecule and are nearly perpendicular to the fused ring plane, as indicated by the C-N-C-C torsion angles in the range 106.0 (3)-113.4 (3)°. In the crystal, the two mol-ecules are linked through C-H⋯O hydrogen bonds into dimers, which are subsequently linked by further C-H⋯O inter-actions, building a three-dimensional network.

Related literature

For the biological activity of benzimidazole derivatives, see: Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). For examples of benzimidazol-2-one derivatives, see: Ouzidan et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C13H9N3O3

M = 255.23

Orthorhombic,

a = 20.0988 (16) Å

b = 4.2645 (3) Å

c = 28.669 (2) Å

V = 2457.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.48 × 0.2 × 0.13 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (ABSFAC; Agilent, 2012 ▶) T min = 0.520, T max = 1

16703 measured reflections

3233 independent reflections

2971 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.05

3233 reflections

343 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016814/kj2228sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016814/kj2228Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016814/kj2228Isup3.cml

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

C13H9N3O3	F(000) = 1056
Mr = 255.23	Dx = 1.38 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 8380 reflections
a = 20.0988 (16) Å	θ = 1.8–29.7°
b = 4.2645 (3) Å	µ = 0.10 mm−1
c = 28.669 (2) Å	T = 150 K
V = 2457.3 (3) Å3	Prism, colourless
Z = 8	0.48 × 0.2 × 0.13 mm

Agilent Xcalibur (Ruby, Gemini) diffractometer	3233 independent reflections
Graphite monochromator	2971 reflections with I > 2σ(I)
Detector resolution: 10.4752 pixels mm-1	Rint = 0.032
ω–scan	θmax = 29.7°, θmin = 2.0°
Absorption correction: multi-scan (ABSFAC; Agilent, 2012)	h = −27→25
Tmin = 0.520, Tmax = 1	k = −5→5
16703 measured reflections	l = −38→36

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0875P)2 + 0.4146P] where P = (Fo2 + 2Fc2)/3
3233 reflections	(Δ/σ)max = 0.002
343 parameters	Δρmax = 0.48 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.07911 (10)	−0.4511 (5)	0.39515 (8)	0.0308 (5)
O2	0.29627 (10)	0.6066 (6)	0.25710 (8)	0.0407 (5)
O3	0.24251 (12)	0.5944 (5)	0.19215 (8)	0.0398 (5)
N1	0.15605 (10)	−0.1129 (5)	0.36150 (7)	0.0211 (4)
N2	0.07187 (10)	−0.2738 (5)	0.31877 (7)	0.0205 (4)
N3	0.24996 (12)	0.5152 (5)	0.23272 (10)	0.0248 (5)
C1	0.09991 (12)	−0.2962 (6)	0.36290 (9)	0.0225 (5)
C2	0.16290 (13)	0.0211 (5)	0.31805 (10)	0.0185 (5)
C3	0.10972 (10)	−0.0835 (5)	0.29072 (8)	0.0185 (4)
C4	0.21066 (11)	0.2190 (5)	0.30002 (8)	0.0198 (4)
H4	0.2471	0.2922	0.3181	0.024*
C5	0.10186 (14)	0.0045 (5)	0.24439 (10)	0.0208 (5)
H5	0.0655	−0.0683	0.2262	0.025*
C6	0.20185 (11)	0.3042 (5)	0.25370 (8)	0.0206 (4)
C7	0.14964 (12)	0.2035 (6)	0.22587 (9)	0.0226 (5)
H7	0.1466	0.2704	0.1943	0.027*
C8	0.19954 (13)	−0.0708 (6)	0.40183 (9)	0.0257 (5)
H8A	0.1781	−0.1625	0.4297	0.031*
H8B	0.2060	0.1561	0.4076	0.031*
C9	0.26444 (13)	−0.2195 (7)	0.39468 (10)	0.0317 (6)
C10	0.31652 (16)	−0.3400 (10)	0.38963 (14)	0.0501 (9)
H10	0.3586	−0.4374	0.3855	0.060*
C11	0.01090 (12)	−0.4388 (6)	0.30644 (10)	0.0233 (5)
H11A	0.0174	−0.5456	0.2761	0.028*
H11B	0.0020	−0.6018	0.3302	0.028*
C12	−0.04656 (12)	−0.2329 (6)	0.30314 (10)	0.0279 (5)
C13	−0.09362 (15)	−0.0705 (8)	0.29930 (15)	0.0446 (8)
H13	−0.1316	0.0605	0.2962	0.054*
O4	0.32562 (11)	0.4775 (5)	−0.01141 (8)	0.0318 (5)
O5	0.54368 (10)	−0.5661 (5)	0.12857 (8)	0.0394 (5)
O6	0.49109 (12)	−0.5397 (6)	0.19373 (8)	0.0431 (6)
N4	0.40313 (10)	0.1452 (5)	0.02253 (7)	0.0219 (4)
N5	0.31780 (10)	0.3013 (5)	0.06502 (7)	0.0216 (4)
N6	0.49818 (12)	−0.4715 (5)	0.15248 (10)	0.0248 (5)
C14	0.34636 (12)	0.3236 (6)	0.02130 (9)	0.0225 (5)
C15	0.41073 (12)	0.0130 (5)	0.06653 (10)	0.0176 (5)
C16	0.35634 (11)	0.1154 (5)	0.09333 (8)	0.0189 (4)
C17	0.45827 (11)	−0.1800 (5)	0.08478 (8)	0.0200 (4)
H17	0.4950	−0.2527	0.0669	0.024*
C18	0.34914 (13)	0.0292 (6)	0.13955 (10)	0.0215 (5)
H18	0.3124	0.1011	0.1574	0.026*
C19	0.44923 (11)	−0.2632 (5)	0.13144 (9)	0.0210 (4)
C20	0.39648 (11)	−0.1631 (6)	0.15897 (9)	0.0229 (5)
H20	0.3932	−0.2264	0.1907	0.028*
C21	0.44756 (13)	0.1050 (6)	−0.01722 (9)	0.0264 (5)
H21A	0.4536	−0.1217	−0.0234	0.032*
H21B	0.4270	0.2003	−0.0452	0.032*
C22	0.51236 (13)	0.2486 (7)	−0.00918 (10)	0.0317 (6)
C23	0.56438 (16)	0.3678 (10)	−0.00310 (14)	0.0495 (8)
H23	0.6064	0.4642	0.0018	0.059*
C24	0.25700 (13)	0.4618 (6)	0.07741 (10)	0.0236 (5)
H24A	0.2459	0.6155	0.0527	0.028*
H24B	0.2640	0.5791	0.1068	0.028*
C25	0.20067 (12)	0.2450 (6)	0.08344 (10)	0.0280 (5)
C26	0.15561 (15)	0.0767 (8)	0.09000 (14)	0.0414 (8)
H26	0.1190	−0.0598	0.0953	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0307 (10)	0.0354 (9)	0.0264 (12)	−0.0062 (8)	0.0009 (8)	0.0102 (8)
O2	0.0310 (10)	0.0498 (12)	0.0413 (13)	−0.0166 (10)	0.0000 (9)	0.0027 (10)
O3	0.0417 (12)	0.0488 (12)	0.0289 (11)	−0.0105 (10)	0.0098 (9)	0.0089 (10)
N1	0.0216 (9)	0.0238 (9)	0.0178 (9)	−0.0001 (8)	−0.0016 (7)	0.0026 (8)
N2	0.0171 (9)	0.0223 (9)	0.0221 (10)	−0.0024 (7)	−0.0015 (7)	0.0013 (7)
N3	0.0225 (10)	0.0241 (9)	0.0279 (14)	−0.0008 (8)	0.0069 (9)	0.0002 (8)
C1	0.0220 (11)	0.0234 (11)	0.0222 (12)	0.0015 (9)	0.0005 (8)	0.0014 (9)
C2	0.0174 (11)	0.0189 (9)	0.0193 (13)	0.0033 (8)	−0.0014 (9)	0.0001 (8)
C3	0.0159 (9)	0.0190 (10)	0.0206 (11)	0.0024 (8)	0.0020 (8)	−0.0008 (8)
C4	0.0177 (10)	0.0207 (10)	0.0209 (11)	0.0016 (8)	0.0003 (8)	−0.0024 (8)
C5	0.0224 (13)	0.0222 (10)	0.0179 (13)	−0.0014 (8)	−0.0021 (9)	−0.0024 (8)
C6	0.0195 (10)	0.0219 (10)	0.0204 (11)	0.0016 (8)	0.0029 (8)	−0.0024 (8)
C7	0.0251 (11)	0.0255 (10)	0.0171 (10)	0.0006 (9)	0.0002 (9)	−0.0010 (9)
C8	0.0281 (12)	0.0331 (12)	0.0158 (11)	−0.0028 (10)	−0.0055 (9)	0.0021 (9)
C9	0.0282 (13)	0.0429 (14)	0.0239 (12)	−0.0060 (11)	−0.0087 (10)	0.0057 (11)
C10	0.0288 (15)	0.070 (2)	0.051 (2)	0.0051 (16)	−0.0101 (14)	0.0029 (17)
C11	0.0184 (12)	0.0208 (10)	0.0309 (14)	−0.0019 (8)	−0.0017 (10)	−0.0008 (9)
C12	0.0195 (11)	0.0273 (11)	0.0368 (14)	−0.0047 (9)	−0.0009 (10)	−0.0001 (10)
C13	0.0211 (13)	0.0402 (15)	0.072 (2)	0.0006 (12)	−0.0075 (14)	−0.0002 (16)
O4	0.0327 (10)	0.0383 (10)	0.0245 (11)	0.0086 (8)	−0.0002 (8)	0.0102 (8)
O5	0.0267 (10)	0.0508 (12)	0.0408 (12)	0.0158 (9)	0.0005 (9)	0.0101 (10)
O6	0.0449 (13)	0.0591 (14)	0.0253 (11)	0.0161 (10)	−0.0056 (9)	0.0117 (10)
N4	0.0198 (9)	0.0282 (10)	0.0177 (9)	0.0022 (8)	0.0013 (7)	0.0044 (8)
N5	0.0195 (9)	0.0221 (9)	0.0232 (10)	0.0009 (7)	−0.0007 (7)	0.0043 (8)
N6	0.0234 (10)	0.0270 (10)	0.0240 (13)	0.0006 (8)	−0.0081 (9)	0.0032 (8)
C14	0.0201 (11)	0.0233 (11)	0.0239 (12)	−0.0003 (9)	−0.0012 (8)	0.0027 (9)
C15	0.0173 (10)	0.0200 (10)	0.0154 (12)	−0.0033 (8)	−0.0017 (9)	−0.0001 (8)
C16	0.0171 (10)	0.0173 (9)	0.0223 (11)	−0.0005 (8)	−0.0001 (8)	0.0005 (8)
C17	0.0160 (9)	0.0220 (10)	0.0220 (11)	−0.0010 (8)	0.0006 (8)	−0.0004 (8)
C18	0.0194 (12)	0.0233 (10)	0.0219 (14)	−0.0015 (8)	0.0036 (10)	0.0006 (9)
C19	0.0180 (10)	0.0195 (9)	0.0255 (11)	−0.0032 (8)	−0.0051 (8)	0.0034 (8)
C20	0.0255 (11)	0.0248 (11)	0.0185 (11)	−0.0035 (9)	−0.0010 (9)	0.0019 (9)
C21	0.0285 (12)	0.0306 (12)	0.0200 (12)	0.0027 (10)	0.0058 (9)	0.0019 (10)
C22	0.0272 (13)	0.0399 (14)	0.0279 (13)	0.0063 (11)	0.0087 (10)	0.0067 (11)
C23	0.0265 (15)	0.068 (2)	0.054 (2)	−0.0045 (15)	0.0038 (13)	0.0026 (17)
C24	0.0189 (11)	0.0226 (10)	0.0292 (14)	0.0044 (9)	0.0016 (10)	0.0016 (9)
C25	0.0204 (11)	0.0264 (11)	0.0372 (14)	0.0067 (10)	0.0006 (10)	−0.0042 (10)
C26	0.0232 (13)	0.0369 (15)	0.064 (2)	−0.0037 (12)	0.0085 (14)	−0.0073 (15)

O1—C1	1.211 (3)	O4—C14	1.218 (3)
O2—N3	1.228 (4)	O5—N6	1.212 (4)
O3—N3	1.220 (4)	O6—N6	1.226 (4)
N1—C1	1.373 (3)	N4—C14	1.372 (3)
N1—C2	1.377 (3)	N4—C15	1.390 (3)
N1—C8	1.461 (3)	N4—C21	1.458 (3)
N2—C3	1.373 (3)	N5—C16	1.374 (3)
N2—C1	1.388 (3)	N5—C14	1.382 (3)
N2—C11	1.457 (3)	N5—C24	1.445 (3)
N3—C6	1.451 (3)	N6—C19	1.456 (3)
C2—C4	1.379 (3)	C15—C17	1.365 (3)
C2—C3	1.398 (3)	C15—C16	1.406 (4)
C3—C5	1.389 (4)	C16—C18	1.383 (4)
C4—C6	1.388 (3)	C17—C19	1.396 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—C7	1.387 (4)	C18—C20	1.374 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.386 (3)	C19—C20	1.389 (3)
C7—H7	0.9500	C20—H20	0.9500
C8—C9	1.465 (4)	C21—C22	1.458 (4)
C8—H8A	0.9900	C21—H21A	0.9900
C8—H8B	0.9900	C21—H21B	0.9900
C9—C10	1.175 (4)	C22—C23	1.176 (5)
C10—H10	0.9500	C23—H23	0.9500
C11—C12	1.454 (4)	C24—C25	1.472 (4)
C11—H11A	0.9900	C24—H24A	0.9900
C11—H11B	0.9900	C24—H24B	0.9900
C12—C13	1.177 (4)	C25—C26	1.170 (4)
C13—H13	0.9500	C26—H26	0.9500
C1—N1—C2	110.2 (2)	C14—N4—C15	109.9 (2)
C1—N1—C8	122.6 (2)	C14—N4—C21	123.7 (2)
C2—N1—C8	127.2 (2)	C15—N4—C21	126.5 (2)
C3—N2—C1	110.46 (19)	C16—N5—C14	109.97 (19)
C3—N2—C11	127.6 (2)	C16—N5—C24	127.2 (2)
C1—N2—C11	122.0 (2)	C14—N5—C24	122.8 (2)
O3—N3—O2	123.2 (2)	O5—N6—O6	123.7 (2)
O3—N3—C6	119.0 (2)	O5—N6—C19	118.6 (3)
O2—N3—C6	117.8 (3)	O6—N6—C19	117.7 (3)
O1—C1—N1	128.1 (2)	O4—C14—N4	127.1 (2)
O1—C1—N2	126.4 (2)	O4—C14—N5	126.4 (2)
N1—C1—N2	105.5 (2)	N4—C14—N5	106.5 (2)
N1—C2—C4	131.5 (2)	C17—C15—N4	132.0 (2)
N1—C2—C3	107.3 (2)	C17—C15—C16	121.5 (3)
C4—C2—C3	121.2 (2)	N4—C15—C16	106.5 (2)
N2—C3—C5	131.1 (2)	N5—C16—C18	131.4 (2)
N2—C3—C2	106.5 (2)	N5—C16—C15	107.1 (2)
C5—C3—C2	122.5 (2)	C18—C16—C15	121.5 (2)
C2—C4—C6	115.5 (2)	C15—C17—C19	115.4 (2)
C2—C4—H4	122.3	C15—C17—H17	122.3
C6—C4—H4	122.3	C19—C17—H17	122.3
C7—C5—C3	116.9 (2)	C20—C18—C16	118.3 (2)
C7—C5—H5	121.6	C20—C18—H18	120.8
C3—C5—H5	121.6	C16—C18—H18	120.8
C7—C6—C4	124.5 (2)	C20—C19—C17	124.5 (2)
C7—C6—N3	117.2 (2)	C20—C19—N6	117.9 (2)
C4—C6—N3	118.3 (2)	C17—C19—N6	117.6 (2)
C6—C7—C5	119.6 (2)	C18—C20—C19	118.8 (2)
C6—C7—H7	120.2	C18—C20—H20	120.6
C5—C7—H7	120.2	C19—C20—H20	120.6
N1—C8—C9	111.6 (2)	C22—C21—N4	112.0 (2)
N1—C8—H8A	109.3	C22—C21—H21A	109.2
C9—C8—H8A	109.3	N4—C21—H21A	109.2
N1—C8—H8B	109.3	C22—C21—H21B	109.2
C9—C8—H8B	109.3	N4—C21—H21B	109.2
H8A—C8—H8B	108.0	H21A—C21—H21B	107.9
C10—C9—C8	179.0 (3)	C23—C22—C21	179.1 (4)
C9—C10—H10	180.0	C22—C23—H23	180.0
C12—C11—N2	113.1 (2)	N5—C24—C25	112.4 (2)
C12—C11—H11A	109.0	N5—C24—H24A	109.1
N2—C11—H11A	109.0	C25—C24—H24A	109.1
C12—C11—H11B	109.0	N5—C24—H24B	109.1
N2—C11—H11B	109.0	C25—C24—H24B	109.1
H11A—C11—H11B	107.8	H24A—C24—H24B	107.8
C13—C12—C11	178.1 (3)	C26—C25—C24	177.4 (3)
C12—C13—H13	180.0	C25—C26—H26	180.0
C2—N1—C1—O1	179.0 (3)	C15—N4—C14—O4	178.2 (3)
C8—N1—C1—O1	−2.1 (4)	C21—N4—C14—O4	−2.0 (4)
C2—N1—C1—N2	0.2 (3)	C15—N4—C14—N5	−0.4 (3)
C8—N1—C1—N2	179.2 (2)	C21—N4—C14—N5	179.4 (2)
C3—N2—C1—O1	−178.4 (2)	C16—N5—C14—O4	−177.9 (3)
C11—N2—C1—O1	1.1 (4)	C24—N5—C14—O4	0.7 (4)
C3—N2—C1—N1	0.3 (3)	C16—N5—C14—N4	0.7 (3)
C11—N2—C1—N1	179.8 (2)	C24—N5—C14—N4	179.3 (2)
C1—N1—C2—C4	−179.7 (2)	C14—N4—C15—C17	179.8 (2)
C8—N1—C2—C4	1.4 (4)	C21—N4—C15—C17	0.0 (4)
C1—N1—C2—C3	−0.7 (3)	C14—N4—C15—C16	−0.1 (3)
C8—N1—C2—C3	−179.6 (2)	C21—N4—C15—C16	−179.9 (2)
C1—N2—C3—C5	179.3 (2)	C14—N5—C16—C18	178.8 (2)
C11—N2—C3—C5	−0.2 (4)	C24—N5—C16—C18	0.2 (4)
C1—N2—C3—C2	−0.8 (3)	C14—N5—C16—C15	−0.8 (3)
C11—N2—C3—C2	179.8 (2)	C24—N5—C16—C15	−179.3 (2)
N1—C2—C3—N2	0.9 (3)	C17—C15—C16—N5	−179.4 (2)
C4—C2—C3—N2	−180.0 (2)	N4—C15—C16—N5	0.5 (3)
N1—C2—C3—C5	−179.2 (2)	C17—C15—C16—C18	1.0 (3)
C4—C2—C3—C5	0.0 (3)	N4—C15—C16—C18	−179.1 (2)
N1—C2—C4—C6	179.0 (2)	N4—C15—C17—C19	179.4 (2)
C3—C2—C4—C6	0.1 (3)	C16—C15—C17—C19	−0.7 (3)
N2—C3—C5—C7	180.0 (2)	N5—C16—C18—C20	180.0 (2)
C2—C3—C5—C7	0.0 (3)	C15—C16—C18—C20	−0.5 (3)
C2—C4—C6—C7	−0.1 (3)	C15—C17—C19—C20	0.0 (3)
C2—C4—C6—N3	179.3 (2)	C15—C17—C19—N6	179.4 (2)
O3—N3—C6—C7	0.1 (3)	O5—N6—C19—C20	178.4 (2)
O2—N3—C6—C7	179.8 (2)	O6—N6—C19—C20	−2.0 (3)
O3—N3—C6—C4	−179.3 (2)	O5—N6—C19—C17	−1.0 (3)
O2—N3—C6—C4	0.3 (3)	O6—N6—C19—C17	178.5 (2)
C4—C6—C7—C5	0.2 (4)	C16—C18—C20—C19	−0.2 (3)
N3—C6—C7—C5	−179.3 (2)	C17—C19—C20—C18	0.5 (4)
C3—C5—C7—C6	−0.1 (4)	N6—C19—C20—C18	−178.9 (2)
C1—N1—C8—C9	111.8 (3)	C14—N4—C21—C22	113.4 (3)
C2—N1—C8—C9	−69.5 (3)	C15—N4—C21—C22	−66.8 (3)
N1—C8—C9—C10	−144 (20)	N4—C21—C22—C23	−104 (25)
C3—N2—C11—C12	−74.5 (3)	C16—N5—C24—C25	−71.9 (3)
C1—N2—C11—C12	106.0 (3)	C14—N5—C24—C25	109.8 (3)
N2—C11—C12—C13	136 (10)	N5—C24—C25—C26	121 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O6i	0.95	2.43	3.316 (3)	155
C8—H8A···O4ii	0.99	2.28	3.186 (3)	151
C11—H11A···O6i	0.99	2.45	3.257 (4)	139
C13—H13···O2iii	0.95	2.32	3.205 (4)	155
C21—H21B···O1iv	0.99	2.27	3.191 (3)	154
C24—H24B···O3	0.99	2.49	3.350 (4)	146
C26—H26···O5i	0.95	2.40	3.320 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O6i	0.95	2.43	3.316 (3)	155
C8—H8A⋯O4ii	0.99	2.28	3.186 (3)	151
C11—H11A⋯O6i	0.99	2.45	3.257 (4)	139
C13—H13⋯O2iii	0.95	2.32	3.205 (4)	155
C21—H21B⋯O1iv	0.99	2.27	3.191 (3)	154
C24—H24B⋯O3	0.99	2.49	3.350 (4)	146
C26—H26⋯O5i	0.95	2.40	3.320 (4)	164

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