Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benz-imidazole-5-carboxyl-ate.

In the title compound, C(24)H(25)N(3)O(5), the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methyl-ene C atoms forming the flap. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The crystal packing is further stabillized by weak π-π inter-actions between the benzene rings within the benzimidazole ring system [centroid-centroid distance = 3.7955 (7) Å]. A weak C-H⋯π inter-action involving the benzodioxole ring is also present.

Related literature

For the pharmacological appplications of benzimidazole derivatives, see: Grassmann et al. (2002 ▶); Demirayak et al. (2002 ▶); Evans et al. (1997 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Yoon et al. (2012a ▶,b ▶,c ▶)

Experimental

Crystal data

C24H25N3O5

M = 435.47

Monoclinic,

a = 11.1692 (2) Å

b = 11.5498 (2) Å

c = 17.4607 (3) Å

β = 109.210 (1)°

V = 2127.05 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.50 × 0.49 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.980

50292 measured reflections

7050 independent reflections

5762 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.134

S = 1.04

7050 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.38 e Å−3

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 datablock(s) global, I. DOI: 10.1107/S1600536812001420/lh5402sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001420/lh5402Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001420/lh5402Isup3.cml

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

C24H25N3O5	F(000) = 920
Mr = 435.47	Dx = 1.360 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9946 reflections
a = 11.1692 (2) Å	θ = 2.5–31.5°
b = 11.5498 (2) Å	µ = 0.10 mm−1
c = 17.4607 (3) Å	T = 100 K
β = 109.210 (1)°	Block, yellow
V = 2127.05 (6) Å3	0.50 × 0.49 × 0.21 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7050 independent reflections
Radiation source: fine-focus sealed tube	5762 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 31.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→16
Tmin = 0.954, Tmax = 0.980	k = −16→16
50292 measured reflections	l = −23→25

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.8818P] where P = (Fo2 + 2Fc2)/3
7050 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (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	1.36916 (8)	0.64900 (8)	1.00135 (6)	0.02630 (19)
O2	1.46990 (9)	0.52246 (9)	1.09862 (6)	0.0351 (2)
O3	0.53054 (11)	0.16025 (9)	0.79853 (8)	0.0412 (3)
O4	0.75646 (11)	−0.15864 (9)	1.14027 (6)	0.0373 (2)
O5	0.83670 (11)	−0.00736 (10)	1.23064 (6)	0.0413 (3)
N1	1.08459 (9)	0.25301 (8)	1.08845 (5)	0.01863 (18)
N2	0.94409 (9)	0.27310 (8)	0.96239 (5)	0.01759 (18)
N3	0.68842 (9)	0.06821 (9)	0.76740 (6)	0.0242 (2)
C1	1.12627 (10)	0.33875 (9)	1.04755 (6)	0.0178 (2)
C2	1.23809 (11)	0.40311 (10)	1.07214 (6)	0.0198 (2)
H2A	1.3005	0.3910	1.1237	0.024*
C3	1.25516 (11)	0.48569 (9)	1.01862 (7)	0.0201 (2)
C4	1.16207 (11)	0.50423 (10)	0.94229 (7)	0.0215 (2)
H4A	1.1745	0.5640	0.9083	0.026*
C5	1.05304 (11)	0.43769 (10)	0.91560 (7)	0.0209 (2)
H5A	0.9915	0.4487	0.8636	0.025*
C6	1.03832 (10)	0.35349 (9)	0.96927 (6)	0.01764 (19)
C7	0.97710 (10)	0.21525 (9)	1.03573 (6)	0.01711 (19)
C8	0.90606 (10)	0.11885 (9)	1.05532 (6)	0.01784 (19)
C9	0.85386 (11)	0.02908 (10)	1.00098 (7)	0.0210 (2)
H9A	0.8548	0.0344	0.9469	0.025*
C10	0.80006 (11)	−0.06882 (10)	1.02441 (7)	0.0235 (2)
H10A	0.7655	−0.1302	0.9876	0.028*
C11	0.79959 (11)	−0.07201 (10)	1.10277 (7)	0.0230 (2)
C12	0.84914 (11)	0.01780 (11)	1.15672 (7)	0.0231 (2)
C13	0.90412 (11)	0.11341 (10)	1.13575 (7)	0.0207 (2)
H13A	0.9394	0.1734	1.1737	0.025*
C14	1.37606 (12)	0.55209 (10)	1.04449 (7)	0.0231 (2)
C15	1.48387 (12)	0.71957 (11)	1.02515 (8)	0.0285 (3)
H15A	1.5551	0.6761	1.0169	0.034*
H15B	1.5076	0.7413	1.0831	0.034*
C16	1.45570 (18)	0.82402 (18)	0.97368 (14)	0.0613 (6)
H16A	1.5290	0.8762	0.9902	0.092*
H16B	1.3817	0.8636	0.9798	0.092*
H16C	1.4377	0.8017	0.9168	0.092*
C17	0.83289 (10)	0.25829 (10)	0.88998 (6)	0.0194 (2)
H17A	0.7936	0.3348	0.8720	0.023*
H17B	0.7697	0.2093	0.9034	0.023*
C18	0.86814 (11)	0.20207 (12)	0.82103 (7)	0.0253 (2)
H18A	0.9210	0.2562	0.8020	0.030*
H18B	0.9186	0.1313	0.8413	0.030*
C19	0.74954 (12)	0.17057 (12)	0.75023 (7)	0.0282 (3)
H19A	0.6892	0.2362	0.7390	0.034*
H19B	0.7733	0.1570	0.7011	0.034*
C20	0.72393 (14)	−0.04871 (14)	0.75131 (11)	0.0436 (4)
H20A	0.8155	−0.0627	0.7791	0.052*
H20B	0.7041	−0.0617	0.6924	0.052*
C21	0.64389 (16)	−0.12635 (13)	0.78542 (12)	0.0522 (5)
H21A	0.6121	−0.1940	0.7497	0.063*
H21B	0.6939	−0.1544	0.8402	0.063*
C22	0.53501 (15)	−0.05070 (12)	0.78894 (9)	0.0363 (3)
H22A	0.4576	−0.0664	0.7423	0.044*
H22B	0.5162	−0.0642	0.8398	0.044*
C23	0.58101 (12)	0.07147 (11)	0.78574 (7)	0.0249 (2)
C24	0.77364 (13)	−0.11782 (12)	1.22069 (8)	0.0297 (3)
H24A	0.8254	−0.1736	1.2611	0.036*
H24B	0.6904	−0.1096	1.2288	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0228 (4)	0.0255 (4)	0.0303 (4)	−0.0072 (3)	0.0083 (3)	0.0011 (3)
O2	0.0270 (5)	0.0331 (5)	0.0367 (5)	−0.0086 (4)	−0.0010 (4)	0.0027 (4)
O3	0.0344 (6)	0.0334 (5)	0.0616 (7)	0.0032 (4)	0.0238 (5)	−0.0088 (5)
O4	0.0471 (6)	0.0343 (5)	0.0314 (5)	−0.0208 (5)	0.0142 (4)	−0.0004 (4)
O5	0.0557 (7)	0.0490 (6)	0.0199 (4)	−0.0313 (5)	0.0135 (4)	−0.0020 (4)
N1	0.0190 (4)	0.0193 (4)	0.0163 (4)	−0.0022 (3)	0.0041 (3)	−0.0008 (3)
N2	0.0172 (4)	0.0206 (4)	0.0138 (4)	−0.0022 (3)	0.0035 (3)	−0.0012 (3)
N3	0.0183 (4)	0.0263 (5)	0.0240 (5)	0.0014 (4)	0.0014 (4)	−0.0073 (4)
C1	0.0186 (5)	0.0187 (4)	0.0157 (4)	−0.0011 (4)	0.0051 (4)	−0.0018 (3)
C2	0.0195 (5)	0.0209 (5)	0.0173 (5)	−0.0017 (4)	0.0037 (4)	−0.0025 (4)
C3	0.0204 (5)	0.0197 (5)	0.0208 (5)	−0.0036 (4)	0.0078 (4)	−0.0036 (4)
C4	0.0241 (5)	0.0222 (5)	0.0196 (5)	−0.0022 (4)	0.0092 (4)	0.0010 (4)
C5	0.0211 (5)	0.0241 (5)	0.0168 (5)	−0.0013 (4)	0.0052 (4)	0.0010 (4)
C6	0.0171 (5)	0.0194 (4)	0.0163 (4)	−0.0017 (4)	0.0053 (4)	−0.0020 (4)
C7	0.0180 (5)	0.0182 (4)	0.0149 (4)	−0.0002 (4)	0.0051 (4)	−0.0014 (3)
C8	0.0163 (4)	0.0200 (5)	0.0168 (4)	−0.0012 (4)	0.0048 (4)	−0.0009 (4)
C9	0.0215 (5)	0.0233 (5)	0.0193 (5)	−0.0024 (4)	0.0081 (4)	−0.0041 (4)
C10	0.0232 (5)	0.0222 (5)	0.0259 (5)	−0.0046 (4)	0.0092 (4)	−0.0061 (4)
C11	0.0195 (5)	0.0233 (5)	0.0254 (5)	−0.0043 (4)	0.0062 (4)	0.0012 (4)
C12	0.0224 (5)	0.0288 (6)	0.0168 (5)	−0.0061 (4)	0.0047 (4)	0.0009 (4)
C13	0.0200 (5)	0.0245 (5)	0.0165 (4)	−0.0050 (4)	0.0045 (4)	−0.0019 (4)
C14	0.0242 (5)	0.0221 (5)	0.0242 (5)	−0.0045 (4)	0.0094 (4)	−0.0040 (4)
C15	0.0238 (6)	0.0273 (6)	0.0345 (6)	−0.0083 (5)	0.0097 (5)	−0.0031 (5)
C16	0.0378 (9)	0.0587 (11)	0.0704 (12)	−0.0228 (8)	−0.0052 (8)	0.0337 (10)
C17	0.0162 (5)	0.0259 (5)	0.0143 (4)	−0.0013 (4)	0.0027 (4)	−0.0016 (4)
C18	0.0206 (5)	0.0383 (6)	0.0175 (5)	−0.0066 (5)	0.0069 (4)	−0.0073 (4)
C19	0.0254 (6)	0.0418 (7)	0.0159 (5)	−0.0068 (5)	0.0047 (4)	−0.0046 (5)
C20	0.0256 (6)	0.0396 (8)	0.0529 (9)	0.0102 (6)	−0.0042 (6)	−0.0242 (7)
C21	0.0411 (8)	0.0223 (6)	0.0667 (11)	0.0032 (6)	−0.0181 (8)	−0.0037 (7)
C22	0.0425 (8)	0.0291 (6)	0.0320 (7)	−0.0088 (6)	0.0053 (6)	0.0026 (5)
C23	0.0251 (6)	0.0255 (5)	0.0227 (5)	0.0001 (4)	0.0062 (4)	−0.0014 (4)
C24	0.0274 (6)	0.0341 (6)	0.0250 (6)	−0.0085 (5)	0.0054 (5)	0.0079 (5)

O1—C14	1.3373 (15)	C10—C11	1.3704 (17)
O1—C15	1.4588 (15)	C10—H10A	0.9500
O2—C14	1.2071 (15)	C11—C12	1.3880 (17)
O3—C23	1.2256 (16)	C12—C13	1.3706 (16)
O4—C11	1.3672 (14)	C13—H13A	0.9500
O4—C24	1.4330 (17)	C15—C16	1.475 (2)
O5—C12	1.3738 (14)	C15—H15A	0.9900
O5—C24	1.4399 (16)	C15—H15B	0.9900
N1—C7	1.3235 (14)	C16—H16A	0.9800
N1—C1	1.3878 (14)	C16—H16B	0.9800
N2—C6	1.3788 (14)	C16—H16C	0.9800
N2—C7	1.3825 (14)	C17—C18	1.5290 (16)
N2—C17	1.4618 (14)	C17—H17A	0.9900
N3—C23	1.3402 (16)	C17—H17B	0.9900
N3—C19	1.4450 (17)	C18—C19	1.5289 (17)
N3—C20	1.4606 (17)	C18—H18A	0.9900
C1—C2	1.3943 (15)	C18—H18B	0.9900
C1—C6	1.4067 (15)	C19—H19A	0.9900
C2—C3	1.3916 (16)	C19—H19B	0.9900
C2—H2A	0.9500	C20—C21	1.519 (3)
C3—C4	1.4112 (16)	C20—H20A	0.9900
C3—C14	1.4880 (16)	C20—H20B	0.9900
C4—C5	1.3847 (16)	C21—C22	1.515 (2)
C4—H4A	0.9500	C21—H21A	0.9900
C5—C6	1.3971 (15)	C21—H21B	0.9900
C5—H5A	0.9500	C22—C23	1.5090 (18)
C7—C8	1.4714 (15)	C22—H22A	0.9900
C8—C9	1.3968 (15)	C22—H22B	0.9900
C8—C13	1.4130 (15)	C24—H24A	0.9900
C9—C10	1.4031 (16)	C24—H24B	0.9900
C9—H9A	0.9500
C14—O1—C15	115.14 (10)	O1—C15—H15B	110.3
C11—O4—C24	105.89 (10)	C16—C15—H15B	110.3
C12—O5—C24	105.71 (10)	H15A—C15—H15B	108.6
C7—N1—C1	104.97 (9)	C15—C16—H16A	109.5
C6—N2—C7	106.35 (9)	C15—C16—H16B	109.5
C6—N2—C17	124.13 (9)	H16A—C16—H16B	109.5
C7—N2—C17	129.52 (9)	C15—C16—H16C	109.5
C23—N3—C19	123.21 (11)	H16A—C16—H16C	109.5
C23—N3—C20	113.14 (12)	H16B—C16—H16C	109.5
C19—N3—C20	122.67 (12)	N2—C17—C18	111.41 (9)
N1—C1—C2	129.80 (10)	N2—C17—H17A	109.3
N1—C1—C6	109.95 (9)	C18—C17—H17A	109.3
C2—C1—C6	120.20 (10)	N2—C17—H17B	109.3
C3—C2—C1	117.74 (10)	C18—C17—H17B	109.3
C3—C2—H2A	121.1	H17A—C17—H17B	108.0
C1—C2—H2A	121.1	C19—C18—C17	111.01 (10)
C2—C3—C4	121.13 (10)	C19—C18—H18A	109.4
C2—C3—C14	117.42 (10)	C17—C18—H18A	109.4
C4—C3—C14	121.44 (10)	C19—C18—H18B	109.4
C5—C4—C3	121.78 (10)	C17—C18—H18B	109.4
C5—C4—H4A	119.1	H18A—C18—H18B	108.0
C3—C4—H4A	119.1	N3—C19—C18	111.70 (10)
C4—C5—C6	116.43 (10)	N3—C19—H19A	109.3
C4—C5—H5A	121.8	C18—C19—H19A	109.3
C6—C5—H5A	121.8	N3—C19—H19B	109.3
N2—C6—C5	131.70 (10)	C18—C19—H19B	109.3
N2—C6—C1	105.79 (9)	H19A—C19—H19B	107.9
C5—C6—C1	122.50 (10)	N3—C20—C21	103.78 (13)
N1—C7—N2	112.92 (9)	N3—C20—H20A	111.0
N1—C7—C8	121.52 (9)	C21—C20—H20A	111.0
N2—C7—C8	125.53 (9)	N3—C20—H20B	111.0
C9—C8—C13	120.17 (10)	C21—C20—H20B	111.0
C9—C8—C7	122.70 (10)	H20A—C20—H20B	109.0
C13—C8—C7	116.78 (9)	C22—C21—C20	105.03 (12)
C8—C9—C10	121.55 (10)	C22—C21—H21A	110.7
C8—C9—H9A	119.2	C20—C21—H21A	110.7
C10—C9—H9A	119.2	C22—C21—H21B	110.7
C11—C10—C9	117.10 (10)	C20—C21—H21B	110.7
C11—C10—H10A	121.5	H21A—C21—H21B	108.8
C9—C10—H10A	121.5	C23—C22—C21	104.48 (13)
O4—C11—C10	127.99 (11)	C23—C22—H22A	110.9
O4—C11—C12	110.28 (10)	C21—C22—H22A	110.9
C10—C11—C12	121.72 (11)	C23—C22—H22B	110.9
C13—C12—O5	127.89 (11)	C21—C22—H22B	110.9
C13—C12—C11	122.30 (11)	H22A—C22—H22B	108.9
O5—C12—C11	109.79 (10)	O3—C23—N3	124.65 (12)
C12—C13—C8	117.14 (10)	O3—C23—C22	126.37 (13)
C12—C13—H13A	121.4	N3—C23—C22	108.97 (11)
C8—C13—H13A	121.4	O4—C24—O5	108.19 (10)
O2—C14—O1	123.55 (11)	O4—C24—H24A	110.1
O2—C14—C3	123.99 (11)	O5—C24—H24A	110.1
O1—C14—C3	112.46 (10)	O4—C24—H24B	110.1
O1—C15—C16	106.98 (12)	O5—C24—H24B	110.1
O1—C15—H15A	110.3	H24A—C24—H24B	108.4
C16—C15—H15A	110.3
C7—N1—C1—C2	−175.77 (11)	C24—O5—C12—C13	−179.43 (13)
C7—N1—C1—C6	1.68 (12)	C24—O5—C12—C11	−1.18 (15)
N1—C1—C2—C3	−179.21 (11)	O4—C11—C12—C13	177.00 (12)
C6—C1—C2—C3	3.56 (16)	C10—C11—C12—C13	−1.6 (2)
C1—C2—C3—C4	0.43 (16)	O4—C11—C12—O5	−1.37 (15)
C1—C2—C3—C14	−178.59 (10)	C10—C11—C12—O5	180.00 (12)
C2—C3—C4—C5	−3.24 (18)	O5—C12—C13—C8	179.51 (13)
C14—C3—C4—C5	175.73 (11)	C11—C12—C13—C8	1.46 (18)
C3—C4—C5—C6	1.83 (17)	C9—C8—C13—C12	−0.24 (17)
C7—N2—C6—C5	−177.75 (12)	C7—C8—C13—C12	−173.63 (10)
C17—N2—C6—C5	1.48 (18)	C15—O1—C14—O2	−1.08 (18)
C7—N2—C6—C1	0.87 (12)	C15—O1—C14—C3	178.54 (10)
C17—N2—C6—C1	−179.90 (10)	C2—C3—C14—O2	17.46 (18)
C4—C5—C6—N2	−179.30 (11)	C4—C3—C14—O2	−161.55 (12)
C4—C5—C6—C1	2.27 (17)	C2—C3—C14—O1	−162.16 (10)
N1—C1—C6—N2	−1.60 (12)	C4—C3—C14—O1	18.83 (16)
C2—C1—C6—N2	176.14 (10)	C14—O1—C15—C16	−177.39 (14)
N1—C1—C6—C5	177.18 (10)	C6—N2—C17—C18	72.07 (14)
C2—C1—C6—C5	−5.09 (17)	C7—N2—C17—C18	−108.89 (13)
C1—N1—C7—N2	−1.14 (12)	N2—C17—C18—C19	171.60 (10)
C1—N1—C7—C8	176.98 (10)	C23—N3—C19—C18	105.15 (13)
C6—N2—C7—N1	0.17 (12)	C20—N3—C19—C18	−86.92 (14)
C17—N2—C7—N1	−179.00 (10)	C17—C18—C19—N3	−75.98 (14)
C6—N2—C7—C8	−177.86 (10)	C23—N3—C20—C21	−15.83 (15)
C17—N2—C7—C8	2.97 (18)	C19—N3—C20—C21	175.15 (11)
N1—C7—C8—C9	−135.87 (12)	N3—C20—C21—C22	21.08 (15)
N2—C7—C8—C9	42.00 (16)	C20—C21—C22—C23	−19.27 (16)
N1—C7—C8—C13	37.34 (15)	C19—N3—C23—O3	−8.2 (2)
N2—C7—C8—C13	−144.79 (11)	C20—N3—C23—O3	−177.18 (14)
C13—C8—C9—C10	−0.85 (17)	C19—N3—C23—C22	172.53 (11)
C7—C8—C9—C10	172.14 (11)	C20—N3—C23—C22	3.57 (15)
C8—C9—C10—C11	0.72 (18)	C21—C22—C23—O3	−168.92 (15)
C24—O4—C11—C10	−178.17 (13)	C21—C22—C23—N3	10.31 (15)
C24—O4—C11—C12	3.30 (14)	C11—O4—C24—O5	−3.98 (15)
C9—C10—C11—O4	−177.89 (12)	C12—O5—C24—O4	3.19 (15)
C9—C10—C11—C12	0.49 (18)

Cg is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O5i	0.95	2.49	3.4324 (15)	172
C15—H15B···O3ii	0.99	2.52	3.4288 (18)	153
C21—H21A···O3iii	0.99	2.28	3.184 (2)	151
C24—H24B···O3iv	0.99	2.43	3.338 (2)	153
C16—H16B···Cgii	0.98	2.80	3.702 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O5i	0.95	2.49	3.4324 (15)	172
C15—H15B⋯O3ii	0.99	2.52	3.4288 (18)	153
C21—H21A⋯O3iii	0.99	2.28	3.184 (2)	151
C24—H24B⋯O3iv	0.99	2.43	3.338 (2)	153
C16—H16B⋯Cgii	0.98	2.80	3.702 (2)	154

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