Methyl 3'-benzyl-4'-(2,4-di-chloro-phen-yl)-1'-methyl-2-oxo-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate.

In the title compound, C27H24Cl2N2O3, the indole ring system is essentially planar, with a maximum deviation of 0.082 (2) Å for the carbonyl C atom. It makes a dihedral angle of 88.53 (6)° with the mean plane of the 4-methyl-pyrrolidine ring, which adopts an envelope conformation with the N atom at the flap position. The mol-ecular structure is stabilized by intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(7) ring motifs, and an intra-molecular π-π inter-action involving the benzyl and di-chloro-substituted benzene rings [centroid-centroid distance = 3.6291 (11) Å]. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming C(7) chains running parallel to [10-1].

Related literature

For the biological activity of spiro-oxindole derivatives, see: Hilton et al. (2000 ▶). For a related crystal structure, see: Karthikeyan et al. (2014 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For bond-length distortions in small rings, see: Allen (1981 ▶).

Experimental

Crystal data

C27H24Cl2N2O3

M = 495.38

Monoclinic,

a = 12.7051 (5) Å

b = 14.1724 (6) Å

c = 14.0322 (6) Å

β = 109.424 (2)°

V = 2382.85 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.30 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

27865 measured reflections

6466 independent reflections

4356 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.00

6466 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.49 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003523/su2699sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003523/su2699Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003523/su2699Isup3.cml

CCDC reference: 888482

Additional supporting information: crystallographic information; 3D view; checkCIF report

C27H24Cl2N2O3	F(000) = 1032
Mr = 495.38	Dx = 1.381 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 6466 reflections
a = 12.7051 (5) Å	θ = 2.1–29.3°
b = 14.1724 (6) Å	µ = 0.31 mm−1
c = 14.0322 (6) Å	T = 293 K
β = 109.424 (2)°	Block, colorless
V = 2382.85 (17) Å3	0.30 × 0.28 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4356 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 29.3°, θmin = 2.1°
ω scans	h = −16→17
27865 measured reflections	k = −19→13
6466 independent reflections	l = −18→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.8129P] where P = (Fo2 + 2Fc2)/3
6466 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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
C1	0.58285 (14)	0.31080 (12)	0.42423 (13)	0.0422 (4)
C2	0.66005 (15)	0.33021 (13)	0.37693 (14)	0.0483 (4)
H2	0.7301	0.3019	0.3985	0.058*
C3	0.63062 (15)	0.39240 (13)	0.29724 (15)	0.0484 (4)
C4	0.52940 (16)	0.43704 (13)	0.26718 (15)	0.0507 (5)
H4	0.5118	0.4809	0.2149	0.061*
C5	0.45350 (15)	0.41603 (13)	0.31561 (14)	0.0459 (4)
H5	0.3848	0.4465	0.2951	0.055*
C6	0.47685 (13)	0.35069 (12)	0.39402 (12)	0.0393 (4)
C7	0.39119 (14)	0.32433 (12)	0.44254 (12)	0.0389 (4)
H7	0.4320	0.2961	0.5082	0.047*
C8	0.32681 (16)	0.40830 (13)	0.46311 (15)	0.0502 (4)
H8A	0.3672	0.4374	0.5275	0.060*
H8B	0.3137	0.4553	0.4102	0.060*
C9	0.18556 (13)	0.30092 (11)	0.38043 (11)	0.0346 (3)
C10	0.12965 (15)	0.34886 (13)	0.27525 (12)	0.0426 (4)
C11	0.00156 (14)	0.24664 (13)	0.29794 (14)	0.0449 (4)
C12	−0.09784 (16)	0.19937 (16)	0.28444 (19)	0.0649 (6)
H12	−0.1569	0.2036	0.2239	0.078*
C13	−0.10630 (18)	0.14611 (16)	0.3634 (2)	0.0670 (6)
H13	−0.1722	0.1139	0.3562	0.080*
C14	−0.01904 (18)	0.13971 (14)	0.45262 (18)	0.0581 (5)
H14	−0.0266	0.1033	0.5051	0.070*
C15	0.08044 (15)	0.18687 (13)	0.46545 (14)	0.0446 (4)
H15	0.1391	0.1829	0.5263	0.054*
C16	0.09119 (13)	0.23953 (12)	0.38709 (12)	0.0373 (4)
C17	0.29931 (12)	0.25062 (11)	0.38356 (11)	0.0311 (3)
C18	0.29733 (13)	0.22452 (11)	0.27577 (11)	0.0339 (3)
H18A	0.2346	0.1824	0.2471	0.041*
H18B	0.2812	0.2819	0.2358	0.041*
C19	0.39826 (12)	0.17915 (11)	0.25989 (11)	0.0334 (3)
C20	0.42743 (15)	0.21109 (13)	0.17845 (13)	0.0447 (4)
H20	0.3863	0.2595	0.1384	0.054*
C21	0.51556 (17)	0.17291 (15)	0.15552 (16)	0.0561 (5)
H21	0.5334	0.1958	0.1007	0.067*
C22	0.57727 (16)	0.10121 (14)	0.21310 (15)	0.0522 (5)
H22	0.6376	0.0759	0.1983	0.063*
C23	0.54893 (15)	0.06731 (13)	0.29259 (14)	0.0464 (4)
H23	0.5897	0.0180	0.3313	0.056*
C24	0.46040 (14)	0.10554 (12)	0.31595 (12)	0.0401 (4)
H24	0.4423	0.0814	0.3702	0.048*
C25	0.30887 (12)	0.16134 (11)	0.44713 (11)	0.0331 (3)
C26	0.25651 (17)	0.00191 (13)	0.44542 (15)	0.0532 (5)
H26A	0.3325	−0.0180	0.4765	0.080*
H26B	0.2161	−0.0455	0.3986	0.080*
H26C	0.2226	0.0109	0.4965	0.080*
C27	0.13946 (19)	0.43922 (15)	0.46547 (17)	0.0609 (5)
H27A	0.1663	0.4751	0.5269	0.091*
H27B	0.0706	0.4089	0.4616	0.091*
H27C	0.1273	0.4806	0.4086	0.091*
N1	0.22212 (12)	0.36773 (10)	0.46454 (10)	0.0426 (3)
N2	0.02779 (13)	0.31006 (12)	0.23303 (11)	0.0521 (4)
H2A	−0.0160	0.3229	0.1730	0.063*
O1	0.16988 (12)	0.41046 (10)	0.23798 (10)	0.0562 (4)
O2	0.35713 (10)	0.15537 (9)	0.53672 (8)	0.0471 (3)
O3	0.25399 (9)	0.08941 (8)	0.39242 (8)	0.0379 (3)
Cl1	0.62311 (4)	0.23046 (4)	0.52348 (4)	0.06078 (16)
Cl2	0.72403 (5)	0.41173 (4)	0.23263 (5)	0.07259 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0388 (9)	0.0436 (9)	0.0367 (9)	−0.0069 (7)	0.0025 (7)	0.0008 (7)
C2	0.0367 (9)	0.0496 (11)	0.0534 (11)	−0.0066 (7)	0.0082 (8)	−0.0034 (8)
C3	0.0468 (10)	0.0445 (10)	0.0570 (11)	−0.0149 (8)	0.0214 (9)	−0.0047 (8)
C4	0.0542 (11)	0.0432 (10)	0.0550 (11)	−0.0088 (8)	0.0185 (9)	0.0090 (8)
C5	0.0411 (9)	0.0446 (10)	0.0488 (10)	−0.0032 (7)	0.0106 (8)	0.0072 (8)
C6	0.0371 (8)	0.0400 (9)	0.0355 (8)	−0.0079 (7)	0.0052 (7)	0.0000 (7)
C7	0.0380 (8)	0.0435 (9)	0.0300 (8)	−0.0073 (7)	0.0044 (6)	0.0007 (7)
C8	0.0594 (11)	0.0451 (10)	0.0478 (11)	−0.0102 (8)	0.0201 (9)	−0.0114 (8)
C9	0.0356 (8)	0.0392 (8)	0.0281 (8)	0.0044 (6)	0.0094 (6)	0.0030 (6)
C10	0.0469 (10)	0.0471 (10)	0.0342 (9)	0.0186 (8)	0.0141 (7)	0.0067 (7)
C11	0.0382 (9)	0.0475 (10)	0.0444 (10)	0.0092 (7)	0.0076 (8)	−0.0071 (8)
C12	0.0387 (10)	0.0653 (14)	0.0781 (16)	0.0025 (9)	0.0025 (10)	−0.0212 (12)
C13	0.0462 (11)	0.0567 (13)	0.1007 (19)	−0.0084 (9)	0.0278 (12)	−0.0159 (13)
C14	0.0586 (12)	0.0504 (11)	0.0786 (15)	−0.0027 (9)	0.0406 (12)	−0.0035 (10)
C15	0.0450 (9)	0.0482 (10)	0.0463 (10)	0.0033 (8)	0.0229 (8)	−0.0004 (8)
C16	0.0338 (8)	0.0415 (9)	0.0371 (9)	0.0057 (6)	0.0125 (7)	−0.0040 (7)
C17	0.0290 (7)	0.0365 (8)	0.0245 (7)	0.0008 (6)	0.0043 (6)	0.0029 (6)
C18	0.0326 (8)	0.0417 (9)	0.0248 (7)	0.0037 (6)	0.0060 (6)	0.0039 (6)
C19	0.0315 (7)	0.0379 (8)	0.0286 (7)	−0.0015 (6)	0.0071 (6)	−0.0019 (6)
C20	0.0495 (10)	0.0466 (10)	0.0420 (10)	0.0084 (8)	0.0205 (8)	0.0100 (8)
C21	0.0635 (12)	0.0614 (12)	0.0562 (12)	0.0072 (10)	0.0369 (10)	0.0125 (10)
C22	0.0440 (10)	0.0588 (12)	0.0603 (12)	0.0069 (8)	0.0263 (9)	−0.0008 (9)
C23	0.0416 (9)	0.0478 (10)	0.0469 (10)	0.0102 (8)	0.0110 (8)	0.0038 (8)
C24	0.0414 (9)	0.0454 (10)	0.0338 (8)	0.0041 (7)	0.0128 (7)	0.0053 (7)
C25	0.0282 (7)	0.0409 (8)	0.0272 (7)	0.0022 (6)	0.0053 (6)	0.0019 (6)
C26	0.0685 (13)	0.0385 (10)	0.0508 (11)	−0.0036 (9)	0.0175 (10)	0.0076 (8)
C27	0.0754 (14)	0.0522 (12)	0.0647 (13)	0.0093 (10)	0.0362 (11)	−0.0085 (10)
N1	0.0498 (8)	0.0424 (8)	0.0365 (8)	0.0002 (6)	0.0156 (6)	−0.0062 (6)
N2	0.0453 (9)	0.0654 (10)	0.0348 (8)	0.0157 (7)	−0.0012 (6)	0.0029 (7)
O1	0.0649 (9)	0.0567 (8)	0.0516 (8)	0.0211 (7)	0.0253 (7)	0.0221 (6)
O2	0.0499 (7)	0.0546 (7)	0.0272 (6)	−0.0063 (6)	0.0000 (5)	0.0084 (5)
O3	0.0422 (6)	0.0362 (6)	0.0320 (6)	−0.0011 (5)	0.0079 (5)	0.0016 (4)
Cl1	0.0510 (3)	0.0749 (4)	0.0453 (3)	0.0069 (2)	0.0010 (2)	0.0180 (2)
Cl2	0.0699 (4)	0.0693 (4)	0.0948 (5)	−0.0121 (3)	0.0490 (3)	0.0052 (3)

C1—C2	1.383 (3)	C14—C15	1.388 (3)
C1—C6	1.390 (2)	C14—H14	0.9300
C1—Cl1	1.7389 (18)	C15—C16	1.373 (2)
C2—C3	1.374 (3)	C15—H15	0.9300
C2—H2	0.9300	C17—C25	1.530 (2)
C3—C4	1.368 (3)	C17—C18	1.549 (2)
C3—Cl2	1.7381 (19)	C18—C19	1.516 (2)
C4—C5	1.384 (2)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.393 (2)	C19—C24	1.385 (2)
C5—H5	0.9300	C19—C20	1.389 (2)
C6—C7	1.510 (2)	C20—C21	1.375 (3)
C7—C8	1.525 (3)	C20—H20	0.9300
C7—C17	1.580 (2)	C21—C22	1.371 (3)
C7—H7	0.9800	C21—H21	0.9300
C8—N1	1.455 (2)	C22—C23	1.368 (3)
C8—H8A	0.9700	C22—H22	0.9300
C8—H8B	0.9700	C23—C24	1.382 (2)
C9—N1	1.463 (2)	C23—H23	0.9300
C9—C16	1.509 (2)	C24—H24	0.9300
C9—C10	1.564 (2)	C25—O2	1.2045 (18)
C9—C17	1.599 (2)	C25—O3	1.3262 (19)
C10—O1	1.214 (2)	C26—O3	1.441 (2)
C10—N2	1.348 (2)	C26—H26A	0.9600
C11—C12	1.386 (3)	C26—H26B	0.9600
C11—C16	1.387 (2)	C26—H26C	0.9600
C11—N2	1.397 (3)	C27—N1	1.462 (2)
C12—C13	1.374 (3)	C27—H27A	0.9600
C12—H12	0.9300	C27—H27B	0.9600
C13—C14	1.372 (3)	C27—H27C	0.9600
C13—H13	0.9300	N2—H2A	0.8600
C2—C1—C6	122.86 (16)	C15—C16—C9	130.97 (15)
C2—C1—Cl1	116.62 (14)	C11—C16—C9	109.45 (15)
C6—C1—Cl1	120.50 (13)	C25—C17—C18	110.14 (12)
C3—C2—C1	118.27 (17)	C25—C17—C7	109.87 (12)
C3—C2—H2	120.9	C18—C17—C7	116.02 (13)
C1—C2—H2	120.9	C25—C17—C9	106.29 (12)
C4—C3—C2	121.40 (17)	C18—C17—C9	111.02 (11)
C4—C3—Cl2	120.08 (15)	C7—C17—C9	102.90 (12)
C2—C3—Cl2	118.51 (15)	C19—C18—C17	120.33 (12)
C3—C4—C5	119.09 (17)	C19—C18—H18A	107.2
C3—C4—H4	120.5	C17—C18—H18A	107.2
C5—C4—H4	120.5	C19—C18—H18B	107.2
C4—C5—C6	122.06 (17)	C17—C18—H18B	107.2
C4—C5—H5	119.0	H18A—C18—H18B	106.9
C6—C5—H5	119.0	C24—C19—C20	117.08 (15)
C1—C6—C5	116.20 (16)	C24—C19—C18	125.91 (14)
C1—C6—C7	122.15 (15)	C20—C19—C18	116.92 (14)
C5—C6—C7	121.65 (15)	C21—C20—C19	121.67 (17)
C6—C7—C8	113.87 (14)	C21—C20—H20	119.2
C6—C7—C17	116.42 (13)	C19—C20—H20	119.2
C8—C7—C17	105.41 (13)	C22—C21—C20	120.30 (17)
C6—C7—H7	106.9	C22—C21—H21	119.8
C8—C7—H7	106.9	C20—C21—H21	119.8
C17—C7—H7	106.9	C23—C22—C21	119.14 (17)
N1—C8—C7	104.15 (14)	C23—C22—H22	120.4
N1—C8—H8A	110.9	C21—C22—H22	120.4
C7—C8—H8A	110.9	C22—C23—C24	120.74 (17)
N1—C8—H8B	110.9	C22—C23—H23	119.6
C7—C8—H8B	110.9	C24—C23—H23	119.6
H8A—C8—H8B	108.9	C23—C24—C19	121.04 (16)
N1—C9—C16	111.63 (12)	C23—C24—H24	119.5
N1—C9—C10	113.75 (13)	C19—C24—H24	119.5
C16—C9—C10	100.84 (13)	O2—C25—O3	122.50 (14)
N1—C9—C17	102.99 (12)	O2—C25—C17	125.52 (14)
C16—C9—C17	118.08 (13)	O3—C25—C17	111.95 (12)
C10—C9—C17	110.01 (12)	O3—C26—H26A	109.5
O1—C10—N2	125.73 (16)	O3—C26—H26B	109.5
O1—C10—C9	126.47 (17)	H26A—C26—H26B	109.5
N2—C10—C9	107.80 (15)	O3—C26—H26C	109.5
C12—C11—C16	121.71 (19)	H26A—C26—H26C	109.5
C12—C11—N2	128.77 (18)	H26B—C26—H26C	109.5
C16—C11—N2	109.43 (16)	N1—C27—H27A	109.5
C13—C12—C11	117.9 (2)	N1—C27—H27B	109.5
C13—C12—H12	121.1	H27A—C27—H27B	109.5
C11—C12—H12	121.1	N1—C27—H27C	109.5
C14—C13—C12	121.1 (2)	H27A—C27—H27C	109.5
C14—C13—H13	119.5	H27B—C27—H27C	109.5
C12—C13—H13	119.5	C8—N1—C27	112.88 (15)
C13—C14—C15	120.8 (2)	C8—N1—C9	106.92 (13)
C13—C14—H14	119.6	C27—N1—C9	114.79 (14)
C15—C14—H14	119.6	C10—N2—C11	112.22 (14)
C16—C15—C14	119.13 (18)	C10—N2—H2A	123.9
C16—C15—H15	120.4	C11—N2—H2A	123.9
C14—C15—H15	120.4	C25—O3—C26	116.46 (13)
C15—C16—C11	119.43 (16)
C6—C1—C2—C3	0.7 (3)	C8—C7—C17—C18	118.92 (15)
Cl1—C1—C2—C3	179.12 (14)	C6—C7—C17—C9	−129.76 (14)
C1—C2—C3—C4	2.4 (3)	C8—C7—C17—C9	−2.49 (16)
C1—C2—C3—Cl2	−176.21 (14)	N1—C9—C17—C25	93.64 (13)
C2—C3—C4—C5	−2.7 (3)	C16—C9—C17—C25	−29.85 (17)
Cl2—C3—C4—C5	175.91 (15)	C10—C9—C17—C25	−144.76 (13)
C3—C4—C5—C6	−0.1 (3)	N1—C9—C17—C18	−146.58 (13)
C2—C1—C6—C5	−3.2 (3)	C16—C9—C17—C18	89.92 (16)
Cl1—C1—C6—C5	178.40 (13)	C10—C9—C17—C18	−24.99 (18)
C2—C1—C6—C7	176.31 (16)	N1—C9—C17—C7	−21.83 (14)
Cl1—C1—C6—C7	−2.1 (2)	C16—C9—C17—C7	−145.33 (13)
C4—C5—C6—C1	2.9 (3)	C10—C9—C17—C7	99.76 (14)
C4—C5—C6—C7	−176.61 (17)	C25—C17—C18—C19	−64.72 (18)
C1—C6—C7—C8	137.44 (17)	C7—C17—C18—C19	60.85 (19)
C5—C6—C7—C8	−43.1 (2)	C9—C17—C18—C19	177.83 (13)
C1—C6—C7—C17	−99.58 (18)	C17—C18—C19—C24	45.3 (2)
C5—C6—C7—C17	79.9 (2)	C17—C18—C19—C20	−138.30 (16)
C6—C7—C8—N1	155.06 (14)	C24—C19—C20—C21	−1.4 (3)
C17—C7—C8—N1	26.25 (17)	C18—C19—C20—C21	−178.13 (17)
N1—C9—C10—O1	54.9 (2)	C19—C20—C21—C22	0.2 (3)
C16—C9—C10—O1	174.51 (16)	C20—C21—C22—C23	1.0 (3)
C17—C9—C10—O1	−60.1 (2)	C21—C22—C23—C24	−1.0 (3)
N1—C9—C10—N2	−124.69 (15)	C22—C23—C24—C19	−0.2 (3)
C16—C9—C10—N2	−5.07 (16)	C20—C19—C24—C23	1.3 (2)
C17—C9—C10—N2	120.37 (14)	C18—C19—C24—C23	177.76 (16)
C16—C11—C12—C13	1.3 (3)	C18—C17—C25—O2	146.81 (16)
N2—C11—C12—C13	−174.74 (19)	C7—C17—C25—O2	17.8 (2)
C11—C12—C13—C14	−0.2 (3)	C9—C17—C25—O2	−92.85 (18)
C12—C13—C14—C15	−0.1 (3)	C18—C17—C25—O3	−35.14 (17)
C13—C14—C15—C16	−0.7 (3)	C7—C17—C25—O3	−164.13 (12)
C14—C15—C16—C11	1.8 (2)	C9—C17—C25—O3	85.20 (14)
C14—C15—C16—C9	176.90 (16)	C7—C8—N1—C27	−169.79 (15)
C12—C11—C16—C15	−2.2 (3)	C7—C8—N1—C9	−42.64 (17)
N2—C11—C16—C15	174.60 (15)	C16—C9—N1—C8	167.99 (14)
C12—C11—C16—C9	−178.24 (16)	C10—C9—N1—C8	−78.71 (17)
N2—C11—C16—C9	−1.49 (19)	C17—C9—N1—C8	40.32 (16)
N1—C9—C16—C15	−50.5 (2)	C16—C9—N1—C27	−65.99 (18)
C10—C9—C16—C15	−171.62 (17)	C10—C9—N1—C27	47.31 (19)
C17—C9—C16—C15	68.6 (2)	C17—C9—N1—C27	166.33 (14)
N1—C9—C16—C11	125.01 (14)	O1—C10—N2—C11	−174.94 (16)
C10—C9—C16—C11	3.87 (16)	C9—C10—N2—C11	4.64 (19)
C17—C9—C16—C11	−115.93 (15)	C12—C11—N2—C10	174.33 (18)
C6—C7—C17—C25	117.36 (15)	C16—C11—N2—C10	−2.1 (2)
C8—C7—C17—C25	−115.37 (14)	O2—C25—O3—C26	−1.2 (2)
C6—C7—C17—C18	−8.4 (2)	C17—C25—O3—C26	−179.28 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1	0.97	2.31	3.046 (2)	132
C24—H24···O3	0.93	2.52	3.155 (2)	126
N2—H2A···O2i	0.86	2.07	2.924 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O1	0.97	2.31	3.046 (2)	132
C24—H24⋯O3	0.93	2.52	3.155 (2)	126
N2—H2A⋯O2i	0.86	2.07	2.924 (2)	170

Symmetry code: (i) .