Methyl (3S,3'R)-1-methyl-2,2''-dioxo-1',2',3',5',6',7',8',8a'-octa-hydro-dispiro-[indoline-3,2'-indolizine-3',3''-indoline]-1'-carboxyl-ate.

In the title compound, C(25)H(25)N(3)O(4), the central pyrrolidine ring and the two pyrrolidine rings adopt twisted conformations, whereas the piperidine ring in the octa-hydro-indolizine fused ring system adopts a chair conformation. The indoline ring systems are almost perpendicular with respect to the mean plane of the octa-hydro-indolizine ring system, making dihedral angles of 84.4 (5) and 79.4 (5)°. The acetate group attached to the octa-hydro-indolizine ring system assumes an extended conformation. In the crystal, N-H⋯O hydrogen bonds result in the formation of a helical C(7) chain running parallel to [101]. The crystal packing features C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the biological activity of compounds with spiro-pyrrolidine ring systems, see: Sundar et al. (2011 ▶); Crooks & Sommerville (1982 ▶); Stylianakis et al. (2003 ▶). For a related structure, see: Selvanayagam et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli et al. (1983 ▶).

Experimental

Crystal data

C25H25N3O4

M = 431.48

Monoclinic,

a = 10.0516 (3) Å

b = 17.9539 (6) Å

c = 12.4471 (4) Å

β = 105.347 (2)°

V = 2166.17 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.983

27282 measured reflections

6752 independent reflections

4374 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.143

S = 1.03

6752 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037531/zl2499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037531/zl2499Isup2.hkl

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

C25H25N3O4	F(000) = 912
Mr = 431.48	Dx = 1.323 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6752 reflections
a = 10.0516 (3) Å	θ = 2.0–31.0°
b = 17.9539 (6) Å	µ = 0.09 mm−1
c = 12.4471 (4) Å	T = 293 K
β = 105.347 (2)°	Block, white crystalline
V = 2166.17 (12) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	6752 independent reflections
Radiation source: fine-focus sealed tube	4374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 31.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.978, Tmax = 0.983	k = −25→25
27282 measured reflections	l = −17→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.2828P] where P = (Fo2 + 2Fc2)/3
6752 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 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	0.39509 (15)	0.18055 (7)	0.38847 (13)	0.0389 (3)
H1A	0.3661	0.1786	0.3077	0.047*
H1B	0.3520	0.1394	0.4172	0.047*
C2	0.55128 (16)	0.17364 (9)	0.42873 (14)	0.0475 (4)
H2A	0.5783	0.1691	0.5092	0.057*
H2B	0.5803	0.1288	0.3979	0.057*
C3	0.62352 (16)	0.24026 (9)	0.39500 (16)	0.0528 (4)
H3A	0.6072	0.2411	0.3146	0.063*
H3B	0.7222	0.2362	0.4279	0.063*
C4	0.57047 (14)	0.31205 (8)	0.43361 (14)	0.0421 (3)
H4A	0.5954	0.3137	0.5144	0.051*
H4B	0.6125	0.3545	0.4071	0.051*
C5	0.41569 (13)	0.31611 (7)	0.38920 (11)	0.0312 (3)
H5	0.3898	0.3183	0.3076	0.037*
C6	0.20445 (12)	0.26486 (7)	0.39870 (10)	0.0296 (3)
C7	0.19738 (12)	0.35157 (7)	0.42780 (10)	0.0287 (3)
C8	0.34676 (13)	0.37893 (7)	0.43616 (11)	0.0314 (3)
H8	0.3936	0.3815	0.5159	0.038*
C9	0.35351 (14)	0.45585 (7)	0.39114 (14)	0.0411 (3)
C11	0.14592 (16)	0.18861 (8)	0.56175 (13)	0.0434 (3)
H11	0.2242	0.2033	0.6161	0.052*
C12	0.04945 (18)	0.14130 (9)	0.58827 (16)	0.0545 (4)
H12	0.0624	0.1252	0.6613	0.065*
C13	−0.06500 (17)	0.11821 (9)	0.50720 (17)	0.0571 (5)
H13	−0.1290	0.0872	0.5268	0.068*
C14	−0.08675 (15)	0.14005 (8)	0.39767 (15)	0.0475 (4)
H14	−0.1628	0.1233	0.3428	0.057*
C15	0.00836 (13)	0.18761 (7)	0.37260 (12)	0.0357 (3)
C16	0.12326 (13)	0.21318 (7)	0.45356 (11)	0.0332 (3)
C17	0.12949 (14)	0.25295 (7)	0.27335 (11)	0.0349 (3)
C18	0.04727 (17)	0.41569 (8)	0.24454 (12)	0.0447 (3)
H18	0.1102	0.4081	0.2027	0.054*
C19	−0.07771 (19)	0.45125 (9)	0.19857 (15)	0.0575 (5)
H19	−0.0988	0.4670	0.1248	0.069*
C20	−0.17011 (18)	0.46340 (10)	0.25991 (16)	0.0591 (5)
H20	−0.2529	0.4873	0.2269	0.071*
C21	−0.14357 (15)	0.44103 (8)	0.36957 (15)	0.0485 (4)
H21	−0.2065	0.4495	0.4112	0.058*
C22	−0.01959 (13)	0.40548 (7)	0.41489 (12)	0.0344 (3)
C23	0.07557 (13)	0.39205 (7)	0.35351 (11)	0.0325 (3)
C24	0.16580 (13)	0.35799 (7)	0.54149 (11)	0.0315 (3)
N1	0.35207 (10)	0.25114 (6)	0.42717 (9)	0.0302 (2)
N2	0.01226 (12)	0.21398 (7)	0.26806 (10)	0.0399 (3)
H2C	−0.0517	0.2065	0.2077	0.048*
N3	0.03374 (11)	0.38133 (6)	0.52466 (10)	0.0349 (3)
O1	0.38982 (14)	0.45660 (6)	0.29638 (11)	0.0609 (3)
O2	0.33032 (14)	0.51090 (6)	0.43692 (13)	0.0672 (4)
O3	0.16969 (12)	0.27330 (6)	0.19483 (8)	0.0488 (3)
O4	0.24468 (10)	0.34408 (6)	0.63171 (8)	0.0432 (2)
C25	−0.03937 (16)	0.38432 (10)	0.61061 (14)	0.0509 (4)
H25A	0.0221	0.3706	0.6809	0.076*
H25B	−0.1159	0.3504	0.5924	0.076*
H25C	−0.0727	0.4340	0.6154	0.076*
C10	0.4028 (3)	0.52914 (11)	0.2504 (2)	0.0971 (8)
H10A	0.3167	0.5553	0.2378	0.146*
H10B	0.4268	0.5236	0.1811	0.146*
H10C	0.4737	0.5569	0.3017	0.146*

	U11	U22	U33	U12	U13	U23
C1	0.0442 (8)	0.0309 (6)	0.0414 (8)	0.0046 (6)	0.0107 (6)	−0.0048 (6)
C2	0.0450 (8)	0.0427 (8)	0.0523 (9)	0.0141 (6)	0.0088 (7)	−0.0067 (7)
C3	0.0377 (8)	0.0529 (9)	0.0708 (11)	0.0085 (7)	0.0194 (8)	−0.0090 (8)
C4	0.0315 (7)	0.0413 (7)	0.0546 (9)	0.0007 (6)	0.0134 (6)	−0.0045 (7)
C5	0.0314 (6)	0.0300 (6)	0.0329 (7)	0.0007 (5)	0.0099 (5)	−0.0019 (5)
C6	0.0296 (6)	0.0300 (6)	0.0278 (6)	−0.0002 (5)	0.0050 (5)	−0.0023 (5)
C7	0.0267 (6)	0.0308 (6)	0.0269 (6)	0.0012 (5)	0.0042 (5)	−0.0024 (5)
C8	0.0281 (6)	0.0311 (6)	0.0345 (7)	−0.0006 (5)	0.0072 (5)	−0.0050 (5)
C9	0.0332 (7)	0.0304 (7)	0.0605 (10)	−0.0013 (5)	0.0137 (7)	−0.0040 (6)
C11	0.0428 (8)	0.0429 (8)	0.0431 (8)	−0.0014 (6)	0.0086 (6)	0.0068 (6)
C12	0.0558 (10)	0.0529 (9)	0.0585 (11)	0.0014 (8)	0.0218 (8)	0.0191 (8)
C13	0.0422 (9)	0.0482 (9)	0.0847 (14)	−0.0038 (7)	0.0235 (9)	0.0130 (9)
C14	0.0323 (7)	0.0394 (8)	0.0696 (11)	−0.0032 (6)	0.0114 (7)	−0.0023 (7)
C15	0.0296 (6)	0.0304 (6)	0.0457 (8)	0.0032 (5)	0.0073 (6)	−0.0040 (6)
C16	0.0320 (6)	0.0295 (6)	0.0371 (7)	−0.0001 (5)	0.0077 (5)	−0.0007 (5)
C17	0.0362 (7)	0.0333 (6)	0.0312 (7)	0.0025 (5)	0.0021 (5)	−0.0042 (5)
C18	0.0539 (9)	0.0390 (8)	0.0361 (8)	0.0001 (6)	0.0031 (7)	0.0017 (6)
C19	0.0641 (11)	0.0469 (9)	0.0455 (9)	0.0034 (8)	−0.0136 (8)	0.0082 (7)
C20	0.0417 (9)	0.0468 (9)	0.0727 (13)	0.0083 (7)	−0.0129 (8)	0.0059 (8)
C21	0.0304 (7)	0.0407 (8)	0.0698 (11)	0.0028 (6)	0.0053 (7)	0.0004 (8)
C22	0.0288 (6)	0.0293 (6)	0.0423 (8)	−0.0009 (5)	0.0046 (6)	−0.0011 (5)
C23	0.0308 (6)	0.0299 (6)	0.0333 (7)	0.0006 (5)	0.0020 (5)	−0.0005 (5)
C24	0.0306 (6)	0.0311 (6)	0.0319 (7)	0.0016 (5)	0.0067 (5)	−0.0028 (5)
N1	0.0283 (5)	0.0279 (5)	0.0333 (6)	0.0015 (4)	0.0061 (4)	−0.0021 (4)
N2	0.0341 (6)	0.0414 (6)	0.0375 (6)	−0.0029 (5)	−0.0020 (5)	−0.0079 (5)
N3	0.0319 (6)	0.0375 (6)	0.0366 (6)	0.0026 (5)	0.0115 (5)	−0.0006 (5)
O1	0.0904 (9)	0.0347 (6)	0.0664 (8)	−0.0031 (6)	0.0362 (7)	0.0076 (5)
O2	0.0742 (8)	0.0343 (6)	0.1035 (11)	0.0019 (5)	0.0418 (8)	−0.0131 (6)
O3	0.0554 (6)	0.0600 (7)	0.0290 (5)	−0.0038 (5)	0.0078 (5)	−0.0021 (5)
O4	0.0426 (6)	0.0548 (6)	0.0282 (5)	0.0092 (5)	0.0024 (4)	−0.0019 (4)
C25	0.0466 (9)	0.0592 (10)	0.0551 (10)	0.0026 (7)	0.0280 (8)	−0.0015 (8)
C10	0.149 (2)	0.0460 (11)	0.110 (2)	−0.0063 (13)	0.0586 (18)	0.0246 (12)

C1—N1	1.4613 (16)	C12—H12	0.9300
C1—C2	1.521 (2)	C13—C14	1.379 (3)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.3778 (19)
C2—C3	1.515 (2)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.394 (2)
C2—H2B	0.9700	C15—N2	1.3949 (19)
C3—C4	1.521 (2)	C17—O3	1.2087 (17)
C3—H3A	0.9700	C17—N2	1.3570 (18)
C3—H3B	0.9700	C18—C23	1.3772 (19)
C4—C5	1.5087 (19)	C18—C19	1.390 (2)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.367 (3)
C5—N1	1.4672 (15)	C19—H19	0.9300
C5—C8	1.5193 (16)	C20—C21	1.380 (3)
C5—H5	0.9800	C20—H20	0.9300
C6—N1	1.4525 (15)	C21—C22	1.3807 (19)
C6—C16	1.5126 (17)	C21—H21	0.9300
C6—C17	1.5574 (19)	C22—C23	1.3942 (18)
C6—C7	1.6041 (17)	C22—N3	1.3980 (18)
C7—C23	1.5109 (18)	C24—O4	1.2169 (16)
C7—C24	1.5344 (17)	C24—N3	1.3543 (16)
C7—C8	1.5569 (17)	N2—H2C	0.8600
C8—C9	1.4987 (18)	N3—C25	1.4503 (17)
C8—H8	0.9800	O1—C10	1.442 (2)
C9—O2	1.1942 (17)	C25—H25A	0.9600
C9—O1	1.3237 (19)	C25—H25B	0.9600
C11—C16	1.378 (2)	C25—H25C	0.9600
C11—C12	1.393 (2)	C10—H10A	0.9600
C11—H11	0.9300	C10—H10B	0.9600
C12—C13	1.378 (3)	C10—H10C	0.9600
N1—C1—C2	109.38 (11)	C12—C13—H13	119.3
N1—C1—H1A	109.8	C14—C13—H13	119.3
C2—C1—H1A	109.8	C15—C14—C13	117.52 (15)
N1—C1—H1B	109.8	C15—C14—H14	121.2
C2—C1—H1B	109.8	C13—C14—H14	121.2
H1A—C1—H1B	108.2	C14—C15—C16	122.15 (14)
C3—C2—C1	111.89 (13)	C14—C15—N2	127.88 (14)
C3—C2—H2A	109.2	C16—C15—N2	109.88 (12)
C1—C2—H2A	109.2	C11—C16—C15	119.47 (13)
C3—C2—H2B	109.2	C11—C16—C6	131.94 (12)
C1—C2—H2B	109.2	C15—C16—C6	108.57 (12)
H2A—C2—H2B	107.9	O3—C17—N2	126.05 (13)
C2—C3—C4	110.35 (12)	O3—C17—C6	126.30 (12)
C2—C3—H3A	109.6	N2—C17—C6	107.64 (11)
C4—C3—H3A	109.6	C23—C18—C19	118.39 (15)
C2—C3—H3B	109.6	C23—C18—H18	120.8
C4—C3—H3B	109.6	C19—C18—H18	120.8
H3A—C3—H3B	108.1	C20—C19—C18	121.13 (16)
C5—C4—C3	109.82 (12)	C20—C19—H19	119.4
C5—C4—H4A	109.7	C18—C19—H19	119.4
C3—C4—H4A	109.7	C19—C20—C21	121.61 (15)
C5—C4—H4B	109.7	C19—C20—H20	119.2
C3—C4—H4B	109.7	C21—C20—H20	119.2
H4A—C4—H4B	108.2	C20—C21—C22	117.14 (15)
N1—C5—C4	109.79 (11)	C20—C21—H21	121.4
N1—C5—C8	100.62 (9)	C22—C21—H21	121.4
C4—C5—C8	115.22 (11)	C21—C22—C23	122.14 (14)
N1—C5—H5	110.3	C21—C22—N3	127.87 (13)
C4—C5—H5	110.3	C23—C22—N3	109.91 (11)
C8—C5—H5	110.3	C18—C23—C22	119.57 (13)
N1—C6—C16	115.10 (10)	C18—C23—C7	132.35 (12)
N1—C6—C17	114.40 (10)	C22—C23—C7	108.08 (11)
C16—C6—C17	101.08 (10)	O4—C24—N3	125.36 (12)
N1—C6—C7	102.30 (9)	O4—C24—C7	126.32 (11)
C16—C6—C7	115.59 (10)	N3—C24—C7	108.31 (11)
C17—C6—C7	108.71 (10)	C6—N1—C1	116.04 (10)
C23—C7—C24	101.32 (10)	C6—N1—C5	106.90 (10)
C23—C7—C8	120.00 (11)	C1—N1—C5	113.03 (10)
C24—C7—C8	110.24 (10)	C17—N2—C15	111.60 (11)
C23—C7—C6	113.94 (10)	C17—N2—H2C	124.2
C24—C7—C6	108.26 (10)	C15—N2—H2C	124.2
C8—C7—C6	102.82 (9)	C24—N3—C22	110.72 (11)
C9—C8—C5	118.03 (11)	C24—N3—C25	124.37 (13)
C9—C8—C7	113.84 (10)	C22—N3—C25	124.84 (12)
C5—C8—C7	105.66 (10)	C9—O1—C10	115.98 (15)
C9—C8—H8	106.2	N3—C25—H25A	109.5
C5—C8—H8	106.2	N3—C25—H25B	109.5
C7—C8—H8	106.2	H25A—C25—H25B	109.5
O2—C9—O1	123.47 (14)	N3—C25—H25C	109.5
O2—C9—C8	123.39 (15)	H25A—C25—H25C	109.5
O1—C9—C8	113.14 (12)	H25B—C25—H25C	109.5
C16—C11—C12	118.79 (15)	O1—C10—H10A	109.5
C16—C11—H11	120.6	O1—C10—H10B	109.5
C12—C11—H11	120.6	H10A—C10—H10B	109.5
C13—C12—C11	120.57 (16)	O1—C10—H10C	109.5
C13—C12—H12	119.7	H10A—C10—H10C	109.5
C11—C12—H12	119.7	H10B—C10—H10C	109.5
C12—C13—C14	121.43 (15)
N1—C1—C2—C3	−54.22 (17)	C7—C6—C17—N2	−111.06 (11)
C1—C2—C3—C4	53.92 (19)	C23—C18—C19—C20	0.7 (2)
C2—C3—C4—C5	−55.34 (18)	C18—C19—C20—C21	0.0 (3)
C3—C4—C5—N1	58.10 (15)	C19—C20—C21—C22	−0.2 (2)
C3—C4—C5—C8	170.81 (12)	C20—C21—C22—C23	−0.3 (2)
N1—C6—C7—C23	147.66 (10)	C20—C21—C22—N3	176.32 (14)
C16—C6—C7—C23	−86.48 (13)	C19—C18—C23—C22	−1.2 (2)
C17—C6—C7—C23	26.31 (14)	C19—C18—C23—C7	179.05 (14)
N1—C6—C7—C24	−100.46 (11)	C21—C22—C23—C18	1.0 (2)
C16—C6—C7—C24	25.40 (14)	N3—C22—C23—C18	−176.14 (12)
C17—C6—C7—C24	138.19 (10)	C21—C22—C23—C7	−179.20 (12)
N1—C6—C7—C8	16.20 (11)	N3—C22—C23—C7	3.66 (15)
C16—C6—C7—C8	142.06 (11)	C24—C7—C23—C18	170.03 (14)
C17—C6—C7—C8	−105.16 (11)	C8—C7—C23—C18	48.5 (2)
N1—C5—C8—C9	−163.80 (11)	C6—C7—C23—C18	−73.96 (18)
C4—C5—C8—C9	78.22 (16)	C24—C7—C23—C22	−9.74 (13)
N1—C5—C8—C7	−35.14 (12)	C8—C7—C23—C22	−131.27 (12)
C4—C5—C8—C7	−153.12 (11)	C6—C7—C23—C22	106.27 (12)
C23—C7—C8—C9	15.14 (16)	C23—C7—C24—O4	−167.64 (13)
C24—C7—C8—C9	−101.89 (13)	C8—C7—C24—O4	−39.52 (17)
C6—C7—C8—C9	142.87 (11)	C6—C7—C24—O4	72.24 (16)
C23—C7—C8—C5	−115.95 (12)	C23—C7—C24—N3	12.89 (13)
C24—C7—C8—C5	127.02 (11)	C8—C7—C24—N3	141.01 (11)
C6—C7—C8—C5	11.78 (12)	C6—C7—C24—N3	−107.23 (11)
C5—C8—C9—O2	−163.28 (14)	C16—C6—N1—C1	66.27 (14)
C7—C8—C9—O2	72.00 (19)	C17—C6—N1—C1	−50.20 (15)
C5—C8—C9—O1	15.76 (18)	C7—C6—N1—C1	−167.55 (10)
C7—C8—C9—O1	−108.95 (14)	C16—C6—N1—C5	−166.61 (10)
C16—C11—C12—C13	1.4 (2)	C17—C6—N1—C5	76.93 (12)
C11—C12—C13—C14	1.0 (3)	C7—C6—N1—C5	−40.43 (11)
C12—C13—C14—C15	−1.8 (2)	C2—C1—N1—C6	−177.87 (11)
C13—C14—C15—C16	0.2 (2)	C2—C1—N1—C5	58.12 (15)
C13—C14—C15—N2	176.36 (14)	C4—C5—N1—C6	170.13 (10)
C12—C11—C16—C15	−2.9 (2)	C8—C5—N1—C6	48.25 (12)
C12—C11—C16—C6	178.76 (14)	C4—C5—N1—C1	−60.98 (14)
C14—C15—C16—C11	2.1 (2)	C8—C5—N1—C1	177.14 (10)
N2—C15—C16—C11	−174.62 (12)	O3—C17—N2—C15	169.09 (14)
C14—C15—C16—C6	−179.17 (12)	C6—C17—N2—C15	−9.49 (14)
N2—C15—C16—C6	4.08 (14)	C14—C15—N2—C17	−172.88 (13)
N1—C6—C16—C11	45.73 (19)	C16—C15—N2—C17	3.64 (15)
C17—C6—C16—C11	169.56 (14)	O4—C24—N3—C22	168.88 (13)
C7—C6—C16—C11	−73.29 (18)	C7—C24—N3—C22	−11.64 (14)
N1—C6—C16—C15	−132.75 (11)	O4—C24—N3—C25	−8.2 (2)
C17—C6—C16—C15	−8.92 (13)	C7—C24—N3—C25	171.31 (12)
C7—C6—C16—C15	108.23 (12)	C21—C22—N3—C24	−171.74 (14)
N1—C6—C17—O3	−43.25 (18)	C23—C22—N3—C24	5.19 (15)
C16—C6—C17—O3	−167.55 (14)	C21—C22—N3—C25	5.3 (2)
C7—C6—C17—O3	70.37 (16)	C23—C22—N3—C25	−177.78 (13)
N1—C6—C17—N2	135.32 (11)	O2—C9—O1—C10	1.1 (3)
C16—C6—C17—N2	11.02 (13)	C8—C9—O1—C10	−177.99 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O4i	0.86	2.21	2.9639 (15)	146
C2—H2A···O3ii	0.97	2.48	3.348 (2)	150
C25—H25C···Cg6iii	0.96	2.81	3.5617 (19)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O4i	0.86	2.21	2.9639 (15)	146
C2—H2A⋯O3ii	0.97	2.48	3.348 (2)	150
C25—H25C⋯Cg6iii	0.96	2.81	3.5617 (19)	135

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