Methyl 5''-chloro-1',1''-dimethyl-2,2''-dioxodi-spiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

In the title compound, C22H20ClN3O4, the central pyrrolidine ring adopts an envelope conformation on the N atom. The indolinone systems are individually roughly planar, with maximum deviations from their mean planes of 0.130 Å for the spiro C atom of the indolinone unit and 0.172 Å for the carbonyl C atom of the 5-chloro-1-methyl-indolinone unit. They make dihedral angles of 77.7 (8) and 86.1 (8)° with the mean plane through the central pyrrolidine ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds supported by C-H⋯O contacts into chains along the ab diagonal. The structure also features C-H⋯O hydrogen bonds, forming R 2 (2)(8) and R 2 (2)(16) rings and generating a three-dimensional array.

Related literature

For the biological activity of spiro-pyrrolidine derivatives, see: Obniska et al. (2003 ▶); Peddi et al. (2004 ▶); Kaminski & Obniska (2008 ▶); Stylianakis et al. (2003 ▶); Waldmann (1995 ▶). For the use of optically active pyrrolidines as inter­mediates, chiral ligands or auxiliaries in controlled asymmetric synthesis, see: Suzuki et al. (1994 ▶); Huryn et al. (1991 ▶). For related structures, see: Ganesh et al. (2012 ▶); Wei et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and for hydrogen-bond motifs see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H20ClN3O4

M = 425.86

Monoclinic,

a = 9.2543 (4) Å

b = 18.1387 (7) Å

c = 12.5147 (5) Å

β = 105.026 (2)°

V = 2028.90 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.936, T max = 0.957

18586 measured reflections

5021 independent reflections

3789 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.125

S = 1.06

5021 reflections

278 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011501/sj5312sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011501/sj5312Isup2.hkl

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

C22H20ClN3O4	F(000) = 888
Mr = 425.86	Dx = 1.394 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5021 reflections
a = 9.2543 (4) Å	θ = 2.0–28.3°
b = 18.1387 (7) Å	µ = 0.22 mm−1
c = 12.5147 (5) Å	T = 293 K
β = 105.026 (2)°	Block, colourless
V = 2028.90 (14) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area detector diffractometer	5021 independent reflections
Radiation source: fine-focus sealed tube	3789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.936, Tmax = 0.957	k = −24→24
18586 measured reflections	l = −16→16

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) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.6292P] where P = (Fo2 + 2Fc2)/3
5021 reflections	(Δ/σ)max < 0.001
278 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	0.59371 (19)	0.05207 (9)	0.28439 (13)	0.0423 (4)
C2	0.45435 (17)	0.08424 (8)	0.24338 (12)	0.0358 (3)
H2	0.3891	0.0908	0.2880	0.043*
C3	0.41592 (15)	0.10629 (8)	0.13379 (12)	0.0301 (3)
C4	0.51723 (16)	0.09636 (8)	0.06936 (12)	0.0334 (3)
C5	0.65753 (18)	0.06619 (10)	0.11172 (15)	0.0446 (4)
H5	0.7247	0.0612	0.0683	0.053*
C6	0.69446 (19)	0.04367 (10)	0.22136 (16)	0.0486 (4)
H6	0.7877	0.0228	0.2525	0.058*
C7	0.27545 (15)	0.14084 (8)	0.06175 (11)	0.0294 (3)
C8	0.30532 (17)	0.13446 (8)	−0.05324 (12)	0.0340 (3)
C9	0.11746 (16)	0.10891 (9)	0.05792 (13)	0.0365 (3)
H9	0.0726	0.0954	−0.0194	0.044*
C10	0.02656 (18)	0.17386 (9)	0.08235 (17)	0.0473 (4)
H10A	−0.0777	0.1698	0.0417	0.057*
H10B	0.0331	0.1775	0.1608	0.057*
C11	0.0415 (2)	0.30826 (11)	0.0677 (2)	0.0601 (5)
H11A	0.0551	0.3134	0.1460	0.090*
H11B	−0.0631	0.3117	0.0308	0.090*
H11C	0.0949	0.3467	0.0417	0.090*
C12	0.25861 (16)	0.22640 (8)	0.08568 (12)	0.0319 (3)
C13	0.32532 (18)	0.24031 (8)	0.21214 (13)	0.0361 (3)
C14	0.47566 (18)	0.30011 (8)	0.12068 (13)	0.0362 (3)
C15	0.5915 (2)	0.34053 (11)	0.09938 (15)	0.0489 (4)
H15	0.6722	0.3557	0.1563	0.059*
C16	0.5830 (2)	0.35771 (11)	−0.00992 (16)	0.0536 (5)
H16	0.6609	0.3837	−0.0267	0.064*
C17	0.4617 (2)	0.33718 (11)	−0.09432 (15)	0.0507 (4)
H17	0.4572	0.3508	−0.1668	0.061*
C18	0.3457 (2)	0.29619 (9)	−0.07182 (14)	0.0426 (4)
H18	0.2630	0.2828	−0.1284	0.051*
C19	0.35598 (16)	0.27576 (8)	0.03628 (12)	0.0333 (3)
C20	0.12538 (16)	0.03924 (9)	0.12354 (14)	0.0397 (4)
C21	0.1033 (3)	−0.01945 (12)	0.2852 (2)	0.0683 (6)
H21A	0.0331	−0.0556	0.2467	0.102*
H21B	0.0828	−0.0082	0.3548	0.102*
H21C	0.2030	−0.0385	0.2980	0.102*
C22	0.5254 (2)	0.11715 (12)	−0.12913 (15)	0.0528 (5)
H22A	0.4533	0.1265	−0.1982	0.079*
H22B	0.5717	0.0701	−0.1322	0.079*
H22C	0.6004	0.1550	−0.1158	0.079*
N1	0.45105 (15)	0.11694 (7)	−0.04029 (10)	0.0367 (3)
N2	0.09833 (14)	0.23692 (7)	0.04428 (12)	0.0406 (3)
N3	0.45486 (16)	0.27829 (8)	0.22362 (12)	0.0406 (3)
O1	0.21387 (13)	0.14407 (7)	−0.14168 (9)	0.0467 (3)
O2	0.27254 (15)	0.22036 (7)	0.28633 (10)	0.0516 (3)
O3	0.16251 (15)	−0.01881 (7)	0.09239 (12)	0.0535 (3)
O4	0.08942 (15)	0.04712 (7)	0.21895 (11)	0.0513 (3)
Cl1	0.63981 (7)	0.01829 (3)	0.41915 (4)	0.07053 (19)
H3	0.513 (2)	0.2916 (11)	0.2850 (18)	0.049 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0456 (9)	0.0388 (8)	0.0358 (8)	0.0052 (7)	−0.0016 (7)	0.0025 (6)
C2	0.0376 (8)	0.0349 (7)	0.0336 (8)	0.0014 (6)	0.0071 (6)	0.0003 (6)
C3	0.0270 (6)	0.0294 (7)	0.0325 (7)	−0.0002 (5)	0.0053 (5)	−0.0014 (5)
C4	0.0305 (7)	0.0335 (7)	0.0356 (8)	−0.0014 (6)	0.0076 (6)	−0.0012 (6)
C5	0.0316 (8)	0.0501 (9)	0.0524 (10)	0.0058 (7)	0.0117 (7)	−0.0023 (8)
C6	0.0341 (8)	0.0506 (10)	0.0540 (10)	0.0111 (7)	−0.0014 (7)	−0.0009 (8)
C7	0.0263 (7)	0.0323 (7)	0.0286 (7)	−0.0005 (5)	0.0052 (5)	−0.0001 (5)
C8	0.0367 (8)	0.0330 (7)	0.0310 (7)	−0.0001 (6)	0.0067 (6)	−0.0023 (6)
C9	0.0269 (7)	0.0396 (8)	0.0411 (8)	−0.0036 (6)	0.0054 (6)	0.0015 (6)
C10	0.0304 (8)	0.0446 (9)	0.0689 (12)	0.0030 (7)	0.0162 (8)	0.0085 (8)
C11	0.0521 (11)	0.0455 (10)	0.0865 (15)	0.0154 (8)	0.0250 (10)	0.0088 (10)
C12	0.0308 (7)	0.0327 (7)	0.0323 (7)	0.0014 (6)	0.0082 (6)	0.0022 (6)
C13	0.0410 (8)	0.0346 (7)	0.0343 (8)	0.0038 (6)	0.0130 (6)	−0.0011 (6)
C14	0.0392 (8)	0.0342 (7)	0.0354 (8)	−0.0014 (6)	0.0099 (6)	−0.0026 (6)
C15	0.0441 (9)	0.0532 (10)	0.0481 (10)	−0.0141 (8)	0.0093 (8)	−0.0031 (8)
C16	0.0530 (11)	0.0557 (11)	0.0569 (11)	−0.0133 (8)	0.0231 (9)	0.0038 (9)
C17	0.0635 (11)	0.0524 (10)	0.0403 (9)	−0.0060 (9)	0.0206 (8)	0.0075 (8)
C18	0.0465 (9)	0.0432 (9)	0.0353 (8)	−0.0043 (7)	0.0057 (7)	0.0043 (7)
C19	0.0350 (7)	0.0313 (7)	0.0340 (7)	−0.0006 (6)	0.0100 (6)	−0.0004 (6)
C20	0.0264 (7)	0.0416 (8)	0.0490 (9)	−0.0062 (6)	0.0059 (6)	−0.0003 (7)
C21	0.0829 (16)	0.0602 (13)	0.0651 (14)	0.0020 (11)	0.0252 (12)	0.0181 (10)
C22	0.0556 (11)	0.0664 (12)	0.0441 (10)	0.0031 (9)	0.0265 (8)	0.0001 (8)
N1	0.0373 (7)	0.0425 (7)	0.0319 (6)	0.0029 (5)	0.0122 (5)	−0.0009 (5)
N2	0.0295 (6)	0.0379 (7)	0.0538 (8)	0.0059 (5)	0.0096 (6)	0.0070 (6)
N3	0.0455 (8)	0.0442 (8)	0.0300 (7)	−0.0070 (6)	0.0060 (6)	−0.0053 (6)
O1	0.0484 (7)	0.0567 (7)	0.0291 (6)	0.0048 (6)	−0.0004 (5)	−0.0010 (5)
O2	0.0606 (8)	0.0612 (8)	0.0394 (6)	−0.0015 (6)	0.0243 (6)	0.0023 (6)
O3	0.0497 (7)	0.0394 (7)	0.0746 (9)	0.0012 (5)	0.0218 (7)	−0.0042 (6)
O4	0.0610 (8)	0.0437 (7)	0.0529 (7)	0.0004 (6)	0.0213 (6)	0.0059 (6)
Cl1	0.0869 (4)	0.0727 (4)	0.0425 (3)	0.0259 (3)	−0.0003 (2)	0.0164 (2)

C1—C6	1.377 (3)	C12—N2	1.4514 (18)
C1—C2	1.387 (2)	C12—C19	1.511 (2)
C1—Cl1	1.7403 (17)	C12—C13	1.563 (2)
C2—C3	1.384 (2)	C13—O2	1.2110 (19)
C2—H2	0.9300	C13—N3	1.358 (2)
C3—C4	1.398 (2)	C14—C15	1.381 (2)
C3—C7	1.5125 (19)	C14—C19	1.390 (2)
C4—C5	1.382 (2)	C14—N3	1.408 (2)
C4—N1	1.401 (2)	C15—C16	1.385 (3)
C5—C6	1.387 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.378 (3)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.539 (2)	C17—C18	1.393 (2)
C7—C9	1.5617 (19)	C17—H17	0.9300
C7—C12	1.596 (2)	C18—C19	1.382 (2)
C8—O1	1.2190 (18)	C18—H18	0.9300
C8—N1	1.354 (2)	C20—O3	1.203 (2)
C9—C20	1.499 (2)	C20—O4	1.328 (2)
C9—C10	1.524 (2)	C21—O4	1.452 (2)
C9—H9	0.9800	C21—H21A	0.9600
C10—N2	1.463 (2)	C21—H21B	0.9600
C10—H10A	0.9700	C21—H21C	0.9600
C10—H10B	0.9700	C22—N1	1.451 (2)
C11—N2	1.455 (2)	C22—H22A	0.9600
C11—H11A	0.9600	C22—H22B	0.9600
C11—H11B	0.9600	C22—H22C	0.9600
C11—H11C	0.9600	N3—H3	0.85 (2)
C6—C1—C2	122.50 (15)	C19—C12—C7	113.69 (12)
C6—C1—Cl1	118.94 (13)	C13—C12—C7	108.35 (11)
C2—C1—Cl1	118.52 (14)	O2—C13—N3	126.24 (15)
C3—C2—C1	117.63 (15)	O2—C13—C12	126.59 (15)
C3—C2—H2	121.2	N3—C13—C12	107.17 (13)
C1—C2—H2	121.2	C15—C14—C19	121.86 (15)
C2—C3—C4	119.74 (13)	C15—C14—N3	128.56 (15)
C2—C3—C7	132.13 (13)	C19—C14—N3	109.57 (13)
C4—C3—C7	108.12 (12)	C14—C15—C16	117.50 (16)
C5—C4—C3	122.27 (14)	C14—C15—H15	121.2
C5—C4—N1	127.60 (14)	C16—C15—H15	121.2
C3—C4—N1	110.03 (13)	C17—C16—C15	121.52 (17)
C4—C5—C6	117.53 (15)	C17—C16—H16	119.2
C4—C5—H5	121.2	C15—C16—H16	119.2
C6—C5—H5	121.2	C16—C17—C18	120.42 (16)
C1—C6—C5	120.29 (15)	C16—C17—H17	119.8
C1—C6—H6	119.9	C18—C17—H17	119.8
C5—C6—H6	119.9	C19—C18—C17	118.67 (16)
C3—C7—C8	101.03 (11)	C19—C18—H18	120.7
C3—C7—C9	121.19 (12)	C17—C18—H18	120.7
C8—C7—C9	109.70 (12)	C18—C19—C14	119.87 (14)
C3—C7—C12	113.69 (11)	C18—C19—C12	131.46 (14)
C8—C7—C12	107.37 (11)	C14—C19—C12	108.64 (13)
C9—C7—C12	103.31 (11)	O3—C20—O4	123.00 (16)
O1—C8—N1	125.30 (14)	O3—C20—C9	122.54 (16)
O1—C8—C7	126.00 (14)	O4—C20—C9	114.46 (14)
N1—C8—C7	108.70 (12)	O4—C21—H21A	109.5
C20—C9—C10	119.54 (14)	O4—C21—H21B	109.5
C20—C9—C7	112.55 (12)	H21A—C21—H21B	109.5
C10—C9—C7	105.56 (12)	O4—C21—H21C	109.5
C20—C9—H9	106.1	H21A—C21—H21C	109.5
C10—C9—H9	106.1	H21B—C21—H21C	109.5
C7—C9—H9	106.1	N1—C22—H22A	109.5
N2—C10—C9	102.60 (13)	N1—C22—H22B	109.5
N2—C10—H10A	111.2	H22A—C22—H22B	109.5
C9—C10—H10A	111.2	N1—C22—H22C	109.5
N2—C10—H10B	111.2	H22A—C22—H22C	109.5
C9—C10—H10B	111.2	H22B—C22—H22C	109.5
H10A—C10—H10B	109.2	C8—N1—C4	110.42 (12)
N2—C11—H11A	109.5	C8—N1—C22	124.27 (14)
N2—C11—H11B	109.5	C4—N1—C22	125.28 (14)
H11A—C11—H11B	109.5	C12—N2—C11	115.75 (14)
N2—C11—H11C	109.5	C12—N2—C10	106.81 (12)
H11A—C11—H11C	109.5	C11—N2—C10	114.29 (14)
H11B—C11—H11C	109.5	C13—N3—C14	111.86 (14)
N2—C12—C19	116.02 (12)	C13—N3—H3	125.2 (13)
N2—C12—C13	116.05 (12)	C14—N3—H3	122.7 (13)
C19—C12—C13	101.40 (12)	C20—O4—C21	114.76 (15)
N2—C12—C7	101.61 (11)
C6—C1—C2—C3	2.0 (2)	C19—C12—C13—N3	−11.00 (15)
Cl1—C1—C2—C3	−175.78 (11)	C7—C12—C13—N3	108.91 (13)
C1—C2—C3—C4	−0.6 (2)	C19—C14—C15—C16	1.4 (3)
C1—C2—C3—C7	178.34 (15)	N3—C14—C15—C16	−177.23 (17)
C2—C3—C4—C5	−1.2 (2)	C14—C15—C16—C17	1.8 (3)
C7—C3—C4—C5	179.57 (14)	C15—C16—C17—C18	−2.1 (3)
C2—C3—C4—N1	175.27 (13)	C16—C17—C18—C19	−0.9 (3)
C7—C3—C4—N1	−3.92 (16)	C17—C18—C19—C14	4.1 (2)
C3—C4—C5—C6	1.8 (2)	C17—C18—C19—C12	−173.57 (16)
N1—C4—C5—C6	−174.09 (15)	C15—C14—C19—C18	−4.4 (2)
C2—C1—C6—C5	−1.4 (3)	N3—C14—C19—C18	174.48 (14)
Cl1—C1—C6—C5	176.30 (14)	C15—C14—C19—C12	173.71 (16)
C4—C5—C6—C1	−0.5 (3)	N3—C14—C19—C12	−7.39 (17)
C2—C3—C7—C8	−169.10 (15)	N2—C12—C19—C18	−44.6 (2)
C4—C3—C7—C8	9.95 (15)	C13—C12—C19—C18	−171.21 (16)
C2—C3—C7—C9	−47.8 (2)	C7—C12—C19—C18	72.7 (2)
C4—C3—C7—C9	131.25 (14)	N2—C12—C19—C14	137.60 (14)
C2—C3—C7—C12	76.21 (19)	C13—C12—C19—C14	10.95 (15)
C4—C3—C7—C12	−104.73 (13)	C7—C12—C19—C14	−105.10 (14)
C3—C7—C8—O1	167.44 (15)	C10—C9—C20—O3	161.37 (16)
C9—C7—C8—O1	38.4 (2)	C7—C9—C20—O3	−73.93 (19)
C12—C7—C8—O1	−73.23 (18)	C10—C9—C20—O4	−19.2 (2)
C3—C7—C8—N1	−13.09 (15)	C7—C9—C20—O4	105.49 (15)
C9—C7—C8—N1	−142.15 (13)	O1—C8—N1—C4	−168.84 (15)
C12—C7—C8—N1	106.24 (13)	C7—C8—N1—C4	11.68 (16)
C3—C7—C9—C20	−5.1 (2)	O1—C8—N1—C22	9.1 (3)
C8—C7—C9—C20	111.93 (14)	C7—C8—N1—C22	−170.33 (15)
C12—C7—C9—C20	−133.82 (13)	C5—C4—N1—C8	171.24 (16)
C3—C7—C9—C10	126.97 (15)	C3—C4—N1—C8	−5.04 (17)
C8—C7—C9—C10	−116.01 (14)	C5—C4—N1—C22	−6.7 (3)
C12—C7—C9—C10	−1.77 (15)	C3—C4—N1—C22	177.01 (15)
C20—C9—C10—N2	154.82 (14)	C19—C12—N2—C11	−64.38 (19)
C7—C9—C10—N2	26.84 (17)	C13—C12—N2—C11	54.53 (19)
C3—C7—C12—N2	−157.26 (12)	C7—C12—N2—C11	171.79 (14)
C8—C7—C12—N2	91.88 (13)	C19—C12—N2—C10	167.10 (14)
C9—C7—C12—N2	−24.03 (14)	C13—C12—N2—C10	−73.99 (17)
C3—C7—C12—C19	77.35 (15)	C7—C12—N2—C10	43.27 (15)
C8—C7—C12—C19	−33.51 (15)	C9—C10—N2—C12	−45.11 (17)
C9—C7—C12—C19	−149.42 (12)	C9—C10—N2—C11	−174.47 (15)
C3—C7—C12—C13	−34.55 (16)	O2—C13—N3—C14	−173.29 (16)
C8—C7—C12—C13	−145.41 (12)	C12—C13—N3—C14	7.43 (17)
C9—C7—C12—C13	98.68 (13)	C15—C14—N3—C13	178.58 (17)
N2—C12—C13—O2	43.1 (2)	C19—C14—N3—C13	−0.23 (19)
C19—C12—C13—O2	169.72 (16)	O3—C20—O4—C21	2.0 (2)
C7—C12—C13—O2	−70.37 (19)	C9—C20—O4—C21	−177.38 (16)
N2—C12—C13—N3	−137.63 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.85 (2)	2.18 (2)	2.9112 (18)	143.3 (18)
C15—H15···O1i	0.93	2.46	3.156 (2)	132
C22—H22B···O3ii	0.96	2.56	3.324 (2)	137
C5—H5···O3ii	0.93	2.61	3.499 (2)	160
C9—H9···O3iii	0.98	2.54	3.224 (2)	127
C9—H9···O1	0.98	2.42	2.932 (2)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.85 (2)	2.18 (2)	2.9112 (18)	143.3 (18)
C15—H15⋯O1i	0.93	2.46	3.156 (2)	132
C22—H22B⋯O3ii	0.96	2.56	3.324 (2)	137
C5—H5⋯O3ii	0.93	2.61	3.499 (2)	160
C9—H9⋯O3iii	0.98	2.54	3.224 (2)	127

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