4'-(4-Bromo-phen-yl)-1'-methyl-dispiro-[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione.

In the title compound, C(27)H(20)BrNO(3), the pyrrolidine ring adopts a half-chair conformation, while the other five-membered rings adopt flattened envelope conformations with the spiro C atoms as the flap atoms. An intra-molecular C-H⋯O hydrogen bond occurs, generating an S(6) ring. In the crystal, mol-ecules are connected via weak C-H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For background to tuberculosis, see: Sunduru et al. (2010 ▶); Trivedi et al. (2010 ▶). For background to anti-tuberculous drugs, see: Moraski et al. (2011 ▶); Kumar et al. (2009 ▶); Maheswari et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H20BrNO3

M = 486.35

Monoclinic,

a = 7.8392 (1) Å

b = 21.5849 (5) Å

c = 12.7823 (3) Å

β = 98.422 (1)°

V = 2139.55 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.95 mm−1

T = 100 K

0.42 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.492, T max = 0.788

18795 measured reflections

6300 independent reflections

4709 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.094

S = 1.02

6300 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.72 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/S1600536811044515/hb6460sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044515/hb6460Isup2.hkl

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

C27H20BrNO3	F(000) = 992
Mr = 486.35	Dx = 1.510 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5478 reflections
a = 7.8392 (1) Å	θ = 2.5–29.8°
b = 21.5849 (5) Å	µ = 1.95 mm−1
c = 12.7823 (3) Å	T = 100 K
β = 98.422 (1)°	Block, yellow
V = 2139.55 (8) Å3	0.42 × 0.20 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	6300 independent reflections
Radiation source: fine-focus sealed tube	4709 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 30.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.492, Tmax = 0.788	k = −30→21
18795 measured reflections	l = −18→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0387P)2 + 1.0757P] where P = (Fo2 + 2Fc2)/3
6300 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.72 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 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
Br1	0.43113 (3)	0.100889 (10)	0.065729 (18)	0.03000 (8)
O1	−0.22936 (19)	−0.10044 (7)	0.55329 (11)	0.0260 (3)
O2	−0.0213 (2)	−0.18954 (7)	0.22339 (11)	0.0276 (3)
O3	−0.4454 (2)	−0.15915 (7)	0.21003 (11)	0.0290 (4)
N1	−0.3407 (2)	−0.04677 (8)	0.34244 (13)	0.0215 (4)
C1	0.2608 (2)	0.05064 (9)	0.11634 (15)	0.0204 (4)
C2	0.1755 (3)	0.07378 (10)	0.19495 (16)	0.0219 (4)
H2A	0.2049	0.1132	0.2254	0.026*
C3	0.0460 (3)	0.03840 (9)	0.22887 (15)	0.0203 (4)
H3A	−0.0139	0.0542	0.2826	0.024*
C4	0.0021 (2)	−0.01977 (9)	0.18553 (14)	0.0176 (4)
C5	0.0949 (3)	−0.04220 (9)	0.10800 (15)	0.0203 (4)
H5A	0.0685	−0.0821	0.0785	0.024*
C6	0.2249 (3)	−0.00746 (10)	0.07308 (15)	0.0222 (4)
H6A	0.2876	−0.0233	0.0207	0.027*
C7	−0.1388 (2)	−0.05921 (9)	0.21992 (15)	0.0188 (4)
H7A	−0.1739	−0.0898	0.1621	0.023*
C8	−0.3039 (3)	−0.02450 (10)	0.23916 (16)	0.0224 (4)
H8A	−0.2846	0.0208	0.2408	0.027*
H8B	−0.4008	−0.0342	0.1828	0.027*
C9	−0.2654 (2)	−0.10771 (9)	0.35915 (15)	0.0185 (4)
C10	−0.0832 (2)	−0.09696 (9)	0.32268 (15)	0.0170 (4)
C11	0.0410 (2)	−0.06671 (9)	0.41356 (15)	0.0182 (4)
H11A	0.1157	−0.0356	0.3859	0.022*
H11B	−0.0239	−0.0464	0.4650	0.022*
C12	0.1463 (2)	−0.12043 (9)	0.46402 (15)	0.0187 (4)
C13	0.2532 (3)	−0.12312 (11)	0.56122 (16)	0.0259 (5)
H13A	0.2694	−0.0878	0.6058	0.031*
C14	0.3353 (3)	−0.17868 (12)	0.59126 (17)	0.0320 (5)
H14A	0.4071	−0.1812	0.6578	0.038*
C15	0.3152 (3)	−0.23066 (12)	0.52644 (18)	0.0316 (5)
H15A	0.3717	−0.2682	0.5495	0.038*
C16	0.2136 (3)	−0.22802 (10)	0.42880 (17)	0.0259 (4)
H16A	0.2018	−0.2629	0.3830	0.031*
C17	0.1288 (2)	−0.17243 (9)	0.39946 (15)	0.0192 (4)
C18	0.0067 (2)	−0.15870 (9)	0.30345 (15)	0.0193 (4)
C19	−0.2491 (2)	−0.13185 (10)	0.47401 (15)	0.0203 (4)
C20	−0.2659 (2)	−0.20008 (10)	0.46840 (15)	0.0193 (4)
C21	−0.2248 (3)	−0.24379 (10)	0.54822 (16)	0.0235 (4)
H21A	−0.1788	−0.2315	0.6180	0.028*
C22	−0.2525 (3)	−0.30551 (11)	0.52318 (17)	0.0270 (5)
H22A	−0.2236	−0.3362	0.5761	0.032*
C23	−0.3230 (3)	−0.32353 (10)	0.42047 (18)	0.0274 (5)
H23A	−0.3429	−0.3662	0.4053	0.033*
C24	−0.3641 (3)	−0.28024 (10)	0.34061 (17)	0.0247 (4)
H24A	−0.4117	−0.2926	0.2711	0.030*
C25	−0.3334 (2)	−0.21820 (10)	0.36564 (15)	0.0202 (4)
C26	−0.3611 (3)	−0.16237 (10)	0.29702 (15)	0.0214 (4)
C27	−0.5213 (3)	−0.04025 (11)	0.35822 (17)	0.0282 (5)
H27A	−0.5346	−0.0545	0.4294	0.042*
H27B	−0.5946	−0.0652	0.3056	0.042*
H27C	−0.5556	0.0034	0.3503	0.042*

	U11	U22	U33	U12	U13	U23
Br1	0.02737 (12)	0.02655 (12)	0.03979 (13)	0.00148 (9)	0.01733 (9)	0.00830 (10)
O1	0.0272 (8)	0.0313 (8)	0.0191 (7)	−0.0046 (7)	0.0025 (6)	−0.0031 (6)
O2	0.0340 (9)	0.0244 (8)	0.0241 (7)	−0.0011 (7)	0.0026 (6)	−0.0056 (6)
O3	0.0289 (8)	0.0354 (9)	0.0200 (7)	−0.0075 (7)	−0.0057 (6)	0.0027 (6)
N1	0.0155 (8)	0.0263 (9)	0.0232 (8)	0.0029 (7)	0.0047 (7)	0.0042 (7)
C1	0.0166 (9)	0.0225 (10)	0.0228 (10)	0.0027 (8)	0.0052 (7)	0.0073 (8)
C2	0.0239 (10)	0.0184 (10)	0.0240 (10)	0.0013 (8)	0.0056 (8)	0.0018 (8)
C3	0.0213 (10)	0.0209 (10)	0.0203 (9)	0.0041 (8)	0.0079 (8)	0.0013 (8)
C4	0.0163 (9)	0.0194 (9)	0.0164 (8)	0.0026 (7)	0.0001 (7)	0.0046 (7)
C5	0.0214 (10)	0.0198 (10)	0.0192 (9)	0.0039 (8)	0.0012 (8)	0.0005 (8)
C6	0.0223 (10)	0.0253 (10)	0.0199 (9)	0.0067 (8)	0.0061 (8)	0.0020 (8)
C7	0.0169 (9)	0.0202 (10)	0.0187 (9)	0.0002 (8)	0.0009 (7)	0.0021 (7)
C8	0.0166 (10)	0.0268 (11)	0.0236 (10)	0.0014 (8)	0.0021 (8)	0.0071 (8)
C9	0.0180 (9)	0.0207 (10)	0.0163 (9)	−0.0016 (8)	0.0009 (7)	0.0013 (7)
C10	0.0150 (9)	0.0180 (9)	0.0177 (8)	−0.0012 (7)	0.0011 (7)	0.0015 (7)
C11	0.0164 (9)	0.0186 (10)	0.0191 (9)	−0.0025 (7)	0.0010 (7)	−0.0015 (7)
C12	0.0140 (9)	0.0244 (10)	0.0178 (9)	−0.0021 (8)	0.0024 (7)	0.0024 (8)
C13	0.0187 (10)	0.0400 (13)	0.0190 (10)	−0.0028 (9)	0.0027 (8)	−0.0010 (9)
C14	0.0204 (11)	0.0530 (16)	0.0223 (11)	0.0053 (10)	0.0017 (8)	0.0125 (10)
C15	0.0246 (11)	0.0371 (13)	0.0341 (12)	0.0091 (10)	0.0077 (9)	0.0167 (10)
C16	0.0248 (11)	0.0234 (11)	0.0313 (11)	0.0036 (9)	0.0095 (9)	0.0064 (9)
C17	0.0150 (9)	0.0223 (10)	0.0209 (9)	−0.0006 (8)	0.0048 (7)	0.0044 (8)
C18	0.0182 (9)	0.0185 (9)	0.0215 (9)	−0.0037 (8)	0.0039 (8)	0.0010 (8)
C19	0.0142 (9)	0.0274 (11)	0.0191 (9)	−0.0038 (8)	0.0022 (7)	0.0016 (8)
C20	0.0128 (9)	0.0251 (10)	0.0197 (9)	−0.0036 (8)	0.0011 (7)	0.0011 (8)
C21	0.0188 (10)	0.0320 (12)	0.0189 (9)	−0.0050 (8)	0.0001 (8)	0.0042 (8)
C22	0.0212 (10)	0.0300 (12)	0.0288 (11)	−0.0023 (9)	0.0009 (9)	0.0075 (9)
C23	0.0208 (10)	0.0233 (11)	0.0374 (12)	−0.0034 (8)	0.0020 (9)	−0.0006 (9)
C24	0.0188 (10)	0.0297 (11)	0.0247 (10)	−0.0044 (9)	0.0005 (8)	−0.0030 (9)
C25	0.0161 (9)	0.0249 (10)	0.0194 (9)	−0.0039 (8)	0.0019 (7)	0.0018 (8)
C26	0.0177 (9)	0.0260 (11)	0.0198 (9)	−0.0037 (8)	0.0010 (8)	0.0005 (8)
C27	0.0194 (10)	0.0368 (13)	0.0293 (11)	0.0021 (9)	0.0066 (8)	0.0039 (10)

Br1—C1	1.906 (2)	C11—H11A	0.9900
O1—C19	1.210 (2)	C11—H11B	0.9900
O2—C18	1.214 (2)	C12—C17	1.388 (3)
O3—C26	1.209 (2)	C12—C13	1.394 (3)
N1—C9	1.445 (3)	C13—C14	1.389 (3)
N1—C27	1.466 (3)	C13—H13A	0.9500
N1—C8	1.473 (3)	C14—C15	1.390 (4)
C1—C2	1.379 (3)	C14—H14A	0.9500
C1—C6	1.383 (3)	C15—C16	1.380 (3)
C2—C3	1.390 (3)	C15—H15A	0.9500
C2—H2A	0.9500	C16—C17	1.396 (3)
C3—C4	1.395 (3)	C16—H16A	0.9500
C3—H3A	0.9500	C17—C18	1.472 (3)
C4—C5	1.399 (3)	C19—C20	1.479 (3)
C4—C7	1.510 (3)	C20—C21	1.392 (3)
C5—C6	1.390 (3)	C20—C25	1.398 (3)
C5—H5A	0.9500	C21—C22	1.380 (3)
C6—H6A	0.9500	C21—H21A	0.9500
C7—C8	1.546 (3)	C22—C23	1.403 (3)
C7—C10	1.553 (3)	C22—H22A	0.9500
C7—H7A	1.0000	C23—C24	1.387 (3)
C8—H8A	0.9900	C23—H23A	0.9500
C8—H8B	0.9900	C24—C25	1.390 (3)
C9—C19	1.545 (3)	C24—H24A	0.9500
C9—C26	1.553 (3)	C25—C26	1.488 (3)
C9—C10	1.583 (3)	C27—H27A	0.9800
C10—C18	1.544 (3)	C27—H27B	0.9800
C10—C11	1.546 (3)	C27—H27C	0.9800
C11—C12	1.512 (3)
C9—N1—C27	116.69 (17)	C17—C12—C13	119.36 (19)
C9—N1—C8	107.46 (16)	C17—C12—C11	111.48 (16)
C27—N1—C8	114.35 (16)	C13—C12—C11	129.16 (19)
C2—C1—C6	121.85 (19)	C14—C13—C12	118.4 (2)
C2—C1—Br1	118.66 (16)	C14—C13—H13A	120.8
C6—C1—Br1	119.48 (15)	C12—C13—H13A	120.8
C1—C2—C3	118.85 (19)	C13—C14—C15	121.6 (2)
C1—C2—H2A	120.6	C13—C14—H14A	119.2
C3—C2—H2A	120.6	C15—C14—H14A	119.2
C2—C3—C4	121.30 (18)	C16—C15—C14	120.4 (2)
C2—C3—H3A	119.4	C16—C15—H15A	119.8
C4—C3—H3A	119.4	C14—C15—H15A	119.8
C3—C4—C5	118.01 (18)	C15—C16—C17	117.9 (2)
C3—C4—C7	122.69 (18)	C15—C16—H16A	121.1
C5—C4—C7	119.30 (18)	C17—C16—H16A	121.1
C6—C5—C4	121.49 (19)	C12—C17—C16	122.24 (19)
C6—C5—H5A	119.3	C12—C17—C18	109.19 (17)
C4—C5—H5A	119.3	C16—C17—C18	128.53 (19)
C1—C6—C5	118.46 (18)	O2—C18—C17	127.45 (19)
C1—C6—H6A	120.8	O2—C18—C10	125.27 (18)
C5—C6—H6A	120.8	C17—C18—C10	107.28 (16)
C4—C7—C8	115.99 (17)	O1—C19—C20	126.71 (18)
C4—C7—C10	114.55 (15)	O1—C19—C9	126.11 (19)
C8—C7—C10	104.92 (15)	C20—C19—C9	107.17 (16)
C4—C7—H7A	106.9	C21—C20—C25	120.93 (19)
C8—C7—H7A	106.9	C21—C20—C19	129.02 (18)
C10—C7—H7A	106.9	C25—C20—C19	110.05 (17)
N1—C8—C7	105.26 (15)	C22—C21—C20	118.20 (19)
N1—C8—H8A	110.7	C22—C21—H21A	120.9
C7—C8—H8A	110.7	C20—C21—H21A	120.9
N1—C8—H8B	110.7	C21—C22—C23	120.8 (2)
C7—C8—H8B	110.7	C21—C22—H22A	119.6
H8A—C8—H8B	108.8	C23—C22—H22A	119.6
N1—C9—C19	115.00 (16)	C24—C23—C22	121.3 (2)
N1—C9—C26	117.37 (16)	C24—C23—H23A	119.4
C19—C9—C26	101.32 (15)	C22—C23—H23A	119.4
N1—C9—C10	100.95 (15)	C23—C24—C25	117.79 (19)
C19—C9—C10	112.11 (15)	C23—C24—H24A	121.1
C26—C9—C10	110.47 (16)	C25—C24—H24A	121.1
C18—C10—C11	103.44 (15)	C24—C25—C20	120.99 (19)
C18—C10—C7	113.34 (16)	C24—C25—C26	129.75 (18)
C11—C10—C7	118.79 (16)	C20—C25—C26	109.26 (18)
C18—C10—C9	111.89 (15)	O3—C26—C25	126.98 (19)
C11—C10—C9	109.65 (15)	O3—C26—C9	125.77 (19)
C7—C10—C9	99.93 (14)	C25—C26—C9	107.22 (15)
C12—C11—C10	103.93 (16)	N1—C27—H27A	109.5
C12—C11—H11A	111.0	N1—C27—H27B	109.5
C10—C11—H11A	111.0	H27A—C27—H27B	109.5
C12—C11—H11B	111.0	N1—C27—H27C	109.5
C10—C11—H11B	111.0	H27A—C27—H27C	109.5
H11A—C11—H11B	109.0	H27B—C27—H27C	109.5
C6—C1—C2—C3	−2.2 (3)	C14—C15—C16—C17	−1.9 (3)
Br1—C1—C2—C3	177.23 (14)	C13—C12—C17—C16	0.6 (3)
C1—C2—C3—C4	0.5 (3)	C11—C12—C17—C16	−179.99 (19)
C2—C3—C4—C5	1.2 (3)	C13—C12—C17—C18	178.51 (18)
C2—C3—C4—C7	−179.53 (18)	C11—C12—C17—C18	−2.1 (2)
C3—C4—C5—C6	−1.2 (3)	C15—C16—C17—C12	1.2 (3)
C7—C4—C5—C6	179.50 (17)	C15—C16—C17—C18	−176.3 (2)
C2—C1—C6—C5	2.2 (3)	C12—C17—C18—O2	168.6 (2)
Br1—C1—C6—C5	−177.24 (14)	C16—C17—C18—O2	−13.7 (3)
C4—C5—C6—C1	−0.4 (3)	C12—C17—C18—C10	−11.8 (2)
C3—C4—C7—C8	40.8 (2)	C16—C17—C18—C10	165.9 (2)
C5—C4—C7—C8	−139.97 (18)	C11—C10—C18—O2	−160.17 (19)
C3—C4—C7—C10	−81.7 (2)	C7—C10—C18—O2	−30.2 (3)
C5—C4—C7—C10	97.5 (2)	C9—C10—C18—O2	81.9 (2)
C9—N1—C8—C7	−25.6 (2)	C11—C10—C18—C17	20.3 (2)
C27—N1—C8—C7	−156.81 (17)	C7—C10—C18—C17	150.23 (16)
C4—C7—C8—N1	−131.75 (17)	C9—C10—C18—C17	−97.69 (18)
C10—C7—C8—N1	−4.3 (2)	N1—C9—C19—O1	−29.7 (3)
C27—N1—C9—C19	−65.1 (2)	C26—C9—C19—O1	−157.37 (19)
C8—N1—C9—C19	164.97 (16)	C10—C9—C19—O1	84.8 (2)
C27—N1—C9—C26	53.9 (2)	N1—C9—C19—C20	149.06 (16)
C8—N1—C9—C26	−76.0 (2)	C26—C9—C19—C20	21.41 (19)
C27—N1—C9—C10	174.03 (16)	C10—C9—C19—C20	−96.38 (18)
C8—N1—C9—C10	44.09 (18)	O1—C19—C20—C21	−16.3 (3)
C4—C7—C10—C18	−83.5 (2)	C9—C19—C20—C21	164.93 (19)
C8—C7—C10—C18	148.17 (16)	O1—C19—C20—C25	163.7 (2)
C4—C7—C10—C11	38.2 (2)	C9—C19—C20—C25	−15.0 (2)
C8—C7—C10—C11	−90.1 (2)	C25—C20—C21—C22	−0.1 (3)
C4—C7—C10—C9	157.30 (16)	C19—C20—C21—C22	180.0 (2)
C8—C7—C10—C9	28.97 (18)	C20—C21—C22—C23	−1.0 (3)
N1—C9—C10—C18	−164.44 (15)	C21—C22—C23—C24	1.1 (3)
C19—C9—C10—C18	72.7 (2)	C22—C23—C24—C25	−0.1 (3)
C26—C9—C10—C18	−39.5 (2)	C23—C24—C25—C20	−1.0 (3)
N1—C9—C10—C11	81.38 (17)	C23—C24—C25—C26	178.8 (2)
C19—C9—C10—C11	−41.5 (2)	C21—C20—C25—C24	1.1 (3)
C26—C9—C10—C11	−153.72 (15)	C19—C20—C25—C24	−178.89 (18)
N1—C9—C10—C7	−44.19 (17)	C21—C20—C25—C26	−178.72 (18)
C19—C9—C10—C7	−167.09 (16)	C19—C20—C25—C26	1.3 (2)
C26—C9—C10—C7	80.71 (17)	C24—C25—C26—O3	14.7 (4)
C18—C10—C11—C12	−20.64 (19)	C20—C25—C26—O3	−165.4 (2)
C7—C10—C11—C12	−147.24 (17)	C24—C25—C26—C9	−166.9 (2)
C9—C10—C11—C12	98.86 (17)	C20—C25—C26—C9	13.0 (2)
C10—C11—C12—C17	14.9 (2)	N1—C9—C26—O3	31.6 (3)
C10—C11—C12—C13	−165.8 (2)	C19—C9—C26—O3	157.7 (2)
C17—C12—C13—C14	−1.7 (3)	C10—C9—C26—O3	−83.3 (2)
C11—C12—C13—C14	179.1 (2)	N1—C9—C26—C25	−146.80 (17)
C12—C13—C14—C15	0.9 (3)	C19—C9—C26—C25	−20.7 (2)
C13—C14—C15—C16	0.9 (3)	C10—C9—C26—C25	98.26 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1	0.99	2.40	3.053 (2)	123
C15—H15A···O2i	0.95	2.44	3.163 (3)	133
C22—H22A···O3i	0.95	2.57	3.225 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1	0.99	2.40	3.053 (2)	123
C15—H15A⋯O2i	0.95	2.44	3.163 (3)	133
C22—H22A⋯O3i	0.95	2.57	3.225 (3)	126

Symmetry code: (i) .