4'-Methyl-1H-14',19'-dioxa-4'-aza-spiro-[indole-3,5'-tetra-cyclo-[18.4.0.0(2,6).0(8,13)]tetra-cosa-ne]-1'(24'),8',10',12',20',22'-hexa-ene-2,7'(3H)-dione.

In the title compound, C29H28N2O4, the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced by 0.643 (2) Å from the mean plane formed by the remaining ring atoms. The pyrrolidine ring makes a dihedral angle of 86.1 (8)° with the indoline ring system. In the crystal, N-H⋯O hydrogen bonds result in the formation of cyclic centrosymmetric dimers [R2(2)(8)]. C-H⋯π inter-actions also occur, leading to a chain along the b-axis direction. There is a rather weak π-π electron inter-action between the pyrrazole and benzene rings, with a centroid-centroid distance of 3.765 (1) Å.

Related literature

For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995 ▶). For related structures, see: Ganesh et al. (2012 ▶); Narayanan et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C29H28N2O4

M = 468.53

Triclinic,

a = 9.4223 (3) Å

b = 10.5115 (3) Å

c = 14.1754 (5) Å

α = 70.235 (2)°

β = 87.309 (3)°

γ = 69.065 (2)°

V = 1229.67 (7) Å3

Z = 2

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, 2008 ▶) T min = 0.979, T max = 0.984

22180 measured reflections

5998 independent reflections

4260 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.147

S = 1.01

5998 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.27 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, 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/S1600536812046132/pv2600sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046132/pv2600Isup2.hkl

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

C29H28N2O4	Z = 2
Mr = 468.53	F(000) = 496
Triclinic, P1	Dx = 1.265 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4223 (3) Å	Cell parameters from 5998 reflections
b = 10.5115 (3) Å	θ = 1.5–28.3°
c = 14.1754 (5) Å	µ = 0.09 mm−1
α = 70.235 (2)°	T = 293 K
β = 87.309 (3)°	Block, colorless
γ = 69.065 (2)°	0.25 × 0.22 × 0.19 mm
V = 1229.67 (7) Å3

Bruker APEXII CCD area detector diffractometer	5998 independent reflections
Radiation source: fine-focus sealed tube	4260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −12→12
Tmin = 0.979, Tmax = 0.984	k = −13→12
22180 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.3628P] where P = (Fo2 + 2Fc2)/3
5998 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.27 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	0.44418 (17)	0.81009 (18)	0.29447 (12)	0.0442 (4)
H1A	0.3946	0.7414	0.3256	0.053*
H1B	0.5502	0.7575	0.2883	0.053*
C2	0.36234 (16)	0.91660 (17)	0.19251 (11)	0.0390 (3)
H2	0.4231	0.9763	0.1617	0.047*
C3	0.21938 (15)	1.01176 (16)	0.22618 (10)	0.0348 (3)
H3	0.1490	0.9592	0.2438	0.042*
C4	0.27685 (16)	1.01883 (17)	0.32641 (11)	0.0363 (3)
C5	0.16358 (16)	0.99095 (17)	0.40634 (11)	0.0388 (3)
C6	0.16331 (17)	1.21653 (18)	0.38333 (11)	0.0413 (3)
C7	0.1279 (2)	1.3514 (2)	0.39076 (15)	0.0548 (4)
H7	0.0538	1.3844	0.4314	0.066*
C8	0.2075 (2)	1.4365 (2)	0.33506 (16)	0.0624 (5)
H8	0.1861	1.5284	0.3383	0.075*
C9	0.3177 (2)	1.3870 (2)	0.27514 (16)	0.0591 (5)
H9	0.3700	1.4456	0.2389	0.071*
C10	0.35165 (19)	1.25080 (19)	0.26815 (13)	0.0483 (4)
H10	0.4261	1.2177	0.2277	0.058*
C11	0.27254 (16)	1.16546 (17)	0.32249 (11)	0.0391 (3)
C12	0.4820 (2)	0.8338 (2)	0.45746 (14)	0.0600 (5)
H12A	0.4254	0.7730	0.4891	0.090*
H12B	0.4661	0.9054	0.4886	0.090*
H12C	0.5886	0.7756	0.4648	0.090*
C13	0.13484 (17)	1.15881 (17)	0.14799 (11)	0.0410 (3)
C14	−0.01066 (18)	1.25884 (17)	0.17087 (12)	0.0431 (4)
C15	−0.0379 (2)	1.4067 (2)	0.13226 (14)	0.0559 (5)
H15	0.0331	1.4388	0.0936	0.067*
C16	−0.1679 (3)	1.5065 (2)	0.15010 (19)	0.0705 (6)
H16	−0.1857	1.6052	0.1224	0.085*
C17	−0.2714 (3)	1.4584 (2)	0.20962 (18)	0.0714 (6)
H17	−0.3574	1.5253	0.2238	0.086*
C18	−0.2492 (2)	1.3136 (2)	0.24813 (15)	0.0605 (5)
H18	−0.3201	1.2826	0.2878	0.073*
C19	−0.12012 (18)	1.21319 (18)	0.22752 (13)	0.0465 (4)
C20	−0.2101 (2)	1.0135 (2)	0.29678 (16)	0.0590 (5)
H20A	−0.3031	1.0661	0.2523	0.071*
H20B	−0.2321	1.0224	0.3623	0.071*
C21	−0.1499 (2)	0.8579 (2)	0.30534 (19)	0.0699 (6)
H21A	−0.0474	0.8133	0.3382	0.084*
H21B	−0.2122	0.8103	0.3488	0.084*
C22	−0.1449 (3)	0.8287 (4)	0.2094 (2)	0.0923 (8)
H22A	−0.1226	0.7257	0.2263	0.111*
H22B	−0.2466	0.8790	0.1751	0.111*
C23	−0.0380 (3)	0.8677 (3)	0.13700 (17)	0.0814 (7)
H23A	−0.0434	0.8353	0.0812	0.098*
H23B	−0.0684	0.9724	0.1105	0.098*
C24	0.2312 (2)	0.78928 (19)	0.11634 (12)	0.0484 (4)
C25	0.2379 (3)	0.7110 (2)	0.05322 (15)	0.0645 (5)
H25	0.1613	0.6753	0.0513	0.077*
C26	0.3570 (3)	0.6860 (2)	−0.00634 (15)	0.0742 (7)
H26	0.3613	0.6325	−0.0476	0.089*
C27	0.4695 (3)	0.7399 (2)	−0.00493 (15)	0.0709 (6)
H27	0.5494	0.7241	−0.0458	0.085*
C28	0.4633 (2)	0.8177 (2)	0.05755 (13)	0.0553 (5)
H28	0.5396	0.8544	0.0577	0.066*
C29	0.34579 (18)	0.84291 (17)	0.12054 (11)	0.0424 (4)
N1	0.43033 (14)	0.90587 (15)	0.35091 (10)	0.0425 (3)
N2	0.10136 (15)	1.11034 (15)	0.43241 (10)	0.0443 (3)
H2A	0.0322	1.1202	0.4740	0.053*
O1	0.18613 (16)	1.19738 (15)	0.06779 (9)	0.0620 (4)
O2	0.13719 (13)	0.87891 (13)	0.44025 (9)	0.0485 (3)
O3	−0.09428 (12)	1.06941 (13)	0.25689 (11)	0.0578 (3)
O4	0.11530 (14)	0.80546 (15)	0.18039 (10)	0.0580 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0335 (7)	0.0489 (9)	0.0462 (9)	−0.0082 (6)	0.0004 (6)	−0.0184 (7)
C2	0.0332 (7)	0.0465 (8)	0.0389 (8)	−0.0142 (6)	0.0068 (6)	−0.0173 (6)
C3	0.0308 (6)	0.0425 (8)	0.0331 (7)	−0.0142 (6)	0.0034 (5)	−0.0146 (6)
C4	0.0322 (7)	0.0450 (8)	0.0327 (7)	−0.0149 (6)	0.0035 (5)	−0.0138 (6)
C5	0.0373 (7)	0.0472 (9)	0.0332 (7)	−0.0164 (6)	0.0040 (6)	−0.0145 (6)
C6	0.0411 (8)	0.0470 (9)	0.0372 (8)	−0.0161 (6)	−0.0008 (6)	−0.0155 (7)
C7	0.0540 (10)	0.0516 (10)	0.0590 (11)	−0.0134 (8)	0.0004 (8)	−0.0249 (9)
C8	0.0652 (12)	0.0455 (10)	0.0748 (13)	−0.0191 (9)	−0.0087 (10)	−0.0177 (9)
C9	0.0566 (10)	0.0537 (11)	0.0650 (12)	−0.0298 (9)	−0.0047 (9)	−0.0060 (9)
C10	0.0421 (8)	0.0575 (10)	0.0457 (9)	−0.0239 (7)	0.0010 (7)	−0.0118 (8)
C11	0.0362 (7)	0.0476 (9)	0.0349 (7)	−0.0173 (6)	−0.0013 (6)	−0.0131 (6)
C12	0.0524 (10)	0.0723 (13)	0.0457 (10)	−0.0122 (9)	−0.0117 (8)	−0.0177 (9)
C13	0.0430 (8)	0.0452 (9)	0.0363 (8)	−0.0167 (7)	−0.0014 (6)	−0.0146 (7)
C14	0.0421 (8)	0.0417 (8)	0.0416 (8)	−0.0087 (6)	−0.0092 (6)	−0.0149 (7)
C15	0.0617 (11)	0.0467 (10)	0.0551 (10)	−0.0153 (8)	−0.0118 (8)	−0.0146 (8)
C16	0.0753 (14)	0.0438 (10)	0.0839 (15)	−0.0058 (10)	−0.0191 (12)	−0.0251 (10)
C17	0.0628 (12)	0.0596 (13)	0.0836 (15)	0.0037 (10)	−0.0081 (11)	−0.0403 (11)
C18	0.0449 (9)	0.0651 (12)	0.0643 (12)	−0.0035 (8)	−0.0008 (8)	−0.0303 (10)
C19	0.0382 (8)	0.0463 (9)	0.0491 (9)	−0.0060 (7)	−0.0055 (7)	−0.0181 (7)
C20	0.0375 (8)	0.0751 (13)	0.0644 (12)	−0.0230 (8)	0.0119 (8)	−0.0223 (10)
C21	0.0538 (11)	0.0755 (14)	0.0874 (16)	−0.0374 (10)	0.0172 (10)	−0.0230 (12)
C22	0.0600 (13)	0.130 (2)	0.128 (2)	−0.0507 (15)	0.0145 (14)	−0.078 (2)
C23	0.0672 (13)	0.122 (2)	0.0594 (13)	−0.0371 (14)	−0.0041 (10)	−0.0318 (13)
C24	0.0565 (10)	0.0463 (9)	0.0401 (8)	−0.0138 (7)	−0.0013 (7)	−0.0165 (7)
C25	0.0839 (14)	0.0582 (11)	0.0545 (11)	−0.0209 (10)	−0.0098 (10)	−0.0262 (9)
C26	0.1009 (17)	0.0651 (13)	0.0479 (11)	−0.0059 (12)	−0.0087 (11)	−0.0327 (10)
C27	0.0766 (14)	0.0761 (14)	0.0452 (10)	−0.0013 (11)	0.0078 (9)	−0.0313 (10)
C28	0.0539 (10)	0.0605 (11)	0.0422 (9)	−0.0077 (8)	0.0070 (7)	−0.0206 (8)
C29	0.0443 (8)	0.0416 (8)	0.0350 (8)	−0.0073 (6)	0.0018 (6)	−0.0144 (6)
N1	0.0336 (6)	0.0514 (8)	0.0397 (7)	−0.0111 (5)	−0.0009 (5)	−0.0163 (6)
N2	0.0459 (7)	0.0519 (8)	0.0399 (7)	−0.0203 (6)	0.0139 (6)	−0.0205 (6)
O1	0.0688 (8)	0.0641 (8)	0.0401 (7)	−0.0195 (7)	0.0096 (6)	−0.0077 (6)
O2	0.0527 (7)	0.0497 (7)	0.0469 (6)	−0.0241 (5)	0.0162 (5)	−0.0168 (5)
O3	0.0342 (6)	0.0485 (7)	0.0844 (9)	−0.0120 (5)	0.0118 (6)	−0.0192 (6)
O4	0.0540 (7)	0.0760 (9)	0.0608 (8)	−0.0331 (6)	0.0075 (6)	−0.0345 (7)

C1—N1	1.453 (2)	C15—C16	1.377 (3)
C1—C2	1.526 (2)	C15—H15	0.9300
C1—H1A	0.9700	C16—C17	1.380 (3)
C1—H1B	0.9700	C16—H16	0.9300
C2—C29	1.517 (2)	C17—C18	1.372 (3)
C2—C3	1.530 (2)	C17—H17	0.9300
C2—H2	0.9800	C18—C19	1.392 (2)
C3—C13	1.515 (2)	C18—H18	0.9300
C3—C4	1.5778 (19)	C19—O3	1.356 (2)
C3—H3	0.9800	C20—O3	1.426 (2)
C4—N1	1.4707 (18)	C20—C21	1.490 (3)
C4—C11	1.509 (2)	C20—H20A	0.9700
C4—C5	1.547 (2)	C20—H20B	0.9700
C5—O2	1.2227 (19)	C21—C22	1.488 (4)
C5—N2	1.350 (2)	C21—H21A	0.9700
C6—C7	1.376 (2)	C21—H21B	0.9700
C6—C11	1.388 (2)	C22—C23	1.466 (4)
C6—N2	1.405 (2)	C22—H22A	0.9700
C7—C8	1.390 (3)	C22—H22B	0.9700
C7—H7	0.9300	C23—O4	1.425 (2)
C8—C9	1.379 (3)	C23—H23A	0.9700
C8—H8	0.9300	C23—H23B	0.9700
C9—C10	1.388 (3)	C24—O4	1.387 (2)
C9—H9	0.9300	C24—C25	1.392 (2)
C10—C11	1.382 (2)	C24—C29	1.397 (2)
C10—H10	0.9300	C25—C26	1.375 (3)
C12—N1	1.457 (2)	C25—H25	0.9300
C12—H12A	0.9600	C26—C27	1.372 (3)
C12—H12B	0.9600	C26—H26	0.9300
C12—H12C	0.9600	C27—C28	1.381 (3)
C13—O1	1.211 (2)	C27—H27	0.9300
C13—C14	1.500 (2)	C28—C29	1.397 (2)
C14—C15	1.390 (2)	C28—H28	0.9300
C14—C19	1.398 (2)	N2—H2A	0.8600
N1—C1—C2	102.16 (13)	C15—C16—H16	120.4
N1—C1—H1A	111.3	C17—C16—H16	120.4
C2—C1—H1A	111.3	C18—C17—C16	121.00 (19)
N1—C1—H1B	111.3	C18—C17—H17	119.5
C2—C1—H1B	111.3	C16—C17—H17	119.5
H1A—C1—H1B	109.2	C17—C18—C19	119.7 (2)
C29—C2—C1	113.37 (13)	C17—C18—H18	120.2
C29—C2—C3	119.52 (12)	C19—C18—H18	120.2
C1—C2—C3	100.36 (12)	O3—C19—C18	123.51 (17)
C29—C2—H2	107.6	O3—C19—C14	116.14 (14)
C1—C2—H2	107.6	C18—C19—C14	120.32 (17)
C3—C2—H2	107.6	O3—C20—C21	106.46 (15)
C13—C3—C2	115.22 (12)	O3—C20—H20A	110.4
C13—C3—C4	114.19 (12)	C21—C20—H20A	110.4
C2—C3—C4	104.28 (11)	O3—C20—H20B	110.4
C13—C3—H3	107.6	C21—C20—H20B	110.4
C2—C3—H3	107.6	H20A—C20—H20B	108.6
C4—C3—H3	107.6	C22—C21—C20	116.2 (2)
N1—C4—C11	113.80 (12)	C22—C21—H21A	108.2
N1—C4—C5	114.13 (12)	C20—C21—H21A	108.2
C11—C4—C5	101.31 (12)	C22—C21—H21B	108.2
N1—C4—C3	103.47 (11)	C20—C21—H21B	108.2
C11—C4—C3	116.05 (12)	H21A—C21—H21B	107.4
C5—C4—C3	108.39 (11)	C23—C22—C21	119.24 (19)
O2—C5—N2	126.42 (14)	C23—C22—H22A	107.5
O2—C5—C4	125.33 (14)	C21—C22—H22A	107.5
N2—C5—C4	108.24 (13)	C23—C22—H22B	107.5
C7—C6—C11	122.42 (16)	C21—C22—H22B	107.5
C7—C6—N2	128.30 (16)	H22A—C22—H22B	107.0
C11—C6—N2	109.27 (14)	O4—C23—C22	112.6 (2)
C6—C7—C8	117.32 (18)	O4—C23—H23A	109.1
C6—C7—H7	121.3	C22—C23—H23A	109.1
C8—C7—H7	121.3	O4—C23—H23B	109.1
C9—C8—C7	121.11 (18)	C22—C23—H23B	109.1
C9—C8—H8	119.4	H23A—C23—H23B	107.8
C7—C8—H8	119.4	O4—C24—C25	119.57 (17)
C8—C9—C10	120.86 (18)	O4—C24—C29	119.84 (14)
C8—C9—H9	119.6	C25—C24—C29	120.44 (18)
C10—C9—H9	119.6	C26—C25—C24	120.5 (2)
C11—C10—C9	118.67 (17)	C26—C25—H25	119.7
C11—C10—H10	120.7	C24—C25—H25	119.7
C9—C10—H10	120.7	C27—C26—C25	120.12 (19)
C10—C11—C6	119.61 (16)	C27—C26—H26	119.9
C10—C11—C4	131.19 (15)	C25—C26—H26	119.9
C6—C11—C4	109.15 (13)	C26—C27—C28	119.6 (2)
N1—C12—H12A	109.5	C26—C27—H27	120.2
N1—C12—H12B	109.5	C28—C27—H27	120.2
H12A—C12—H12B	109.5	C27—C28—C29	122.0 (2)
N1—C12—H12C	109.5	C27—C28—H28	119.0
H12A—C12—H12C	109.5	C29—C28—H28	119.0
H12B—C12—H12C	109.5	C28—C29—C24	117.34 (16)
O1—C13—C14	119.75 (15)	C28—C29—C2	116.07 (15)
O1—C13—C3	120.24 (14)	C24—C29—C2	126.43 (14)
C14—C13—C3	119.99 (13)	C1—N1—C12	115.49 (14)
C15—C14—C19	118.30 (16)	C1—N1—C4	108.59 (11)
C15—C14—C13	117.35 (16)	C12—N1—C4	116.17 (13)
C19—C14—C13	124.35 (14)	C5—N2—C6	111.76 (13)
C16—C15—C14	121.4 (2)	C5—N2—H2A	124.1
C16—C15—H15	119.3	C6—N2—H2A	124.1
C14—C15—H15	119.3	C19—O3—C20	121.51 (14)
C15—C16—C17	119.2 (2)	C24—O4—C23	117.83 (15)
N1—C1—C2—C29	−174.22 (12)	C14—C15—C16—C17	1.6 (3)
N1—C1—C2—C3	−45.56 (14)	C15—C16—C17—C18	−2.3 (3)
C29—C2—C3—C13	−74.68 (18)	C16—C17—C18—C19	0.4 (3)
C1—C2—C3—C13	160.78 (13)	C17—C18—C19—O3	−175.51 (17)
C29—C2—C3—C4	159.35 (13)	C17—C18—C19—C14	2.3 (3)
C1—C2—C3—C4	34.82 (14)	C15—C14—C19—O3	175.02 (14)
C13—C3—C4—N1	−138.67 (13)	C13—C14—C19—O3	−4.5 (2)
C2—C3—C4—N1	−12.05 (15)	C15—C14—C19—C18	−2.9 (2)
C13—C3—C4—C11	−13.29 (17)	C13—C14—C19—C18	177.56 (15)
C2—C3—C4—C11	113.32 (14)	O3—C20—C21—C22	−73.7 (2)
C13—C3—C4—C5	99.82 (14)	C20—C21—C22—C23	68.2 (3)
C2—C3—C4—C5	−133.56 (13)	C21—C22—C23—O4	54.5 (4)
N1—C4—C5—O2	−51.95 (19)	O4—C24—C25—C26	−175.97 (17)
C11—C4—C5—O2	−174.67 (14)	C29—C24—C25—C26	−0.4 (3)
C3—C4—C5—O2	62.75 (18)	C24—C25—C26—C27	−0.8 (3)
N1—C4—C5—N2	127.34 (14)	C25—C26—C27—C28	0.8 (3)
C11—C4—C5—N2	4.62 (15)	C26—C27—C28—C29	0.4 (3)
C3—C4—C5—N2	−117.96 (13)	C27—C28—C29—C24	−1.6 (3)
C11—C6—C7—C8	−0.6 (3)	C27—C28—C29—C2	174.00 (16)
N2—C6—C7—C8	179.12 (15)	O4—C24—C29—C28	177.14 (15)
C6—C7—C8—C9	−0.2 (3)	C25—C24—C29—C28	1.6 (2)
C7—C8—C9—C10	0.5 (3)	O4—C24—C29—C2	2.0 (3)
C8—C9—C10—C11	0.1 (3)	C25—C24—C29—C2	−173.54 (16)
C9—C10—C11—C6	−0.8 (2)	C1—C2—C29—C28	−91.08 (17)
C9—C10—C11—C4	176.26 (15)	C3—C2—C29—C28	150.90 (15)
C7—C6—C11—C10	1.1 (2)	C1—C2—C29—C24	84.06 (19)
N2—C6—C11—C10	−178.63 (13)	C3—C2—C29—C24	−34.0 (2)
C7—C6—C11—C4	−176.56 (14)	C2—C1—N1—C12	172.65 (14)
N2—C6—C11—C4	3.68 (16)	C2—C1—N1—C4	40.12 (15)
N1—C4—C11—C10	54.8 (2)	C11—C4—N1—C1	−144.11 (13)
C5—C4—C11—C10	177.73 (15)	C5—C4—N1—C1	100.27 (15)
C3—C4—C11—C10	−65.1 (2)	C3—C4—N1—C1	−17.30 (16)
N1—C4—C11—C6	−127.89 (13)	C11—C4—N1—C12	83.73 (18)
C5—C4—C11—C6	−4.94 (14)	C5—C4—N1—C12	−31.89 (19)
C3—C4—C11—C6	112.18 (14)	C3—C4—N1—C12	−149.46 (14)
C2—C3—C13—O1	−4.4 (2)	O2—C5—N2—C6	176.50 (14)
C4—C3—C13—O1	116.34 (16)	C4—C5—N2—C6	−2.78 (17)
C2—C3—C13—C14	177.33 (13)	C7—C6—N2—C5	179.74 (16)
C4—C3—C13—C14	−61.97 (17)	C11—C6—N2—C5	−0.52 (17)
O1—C13—C14—C15	−34.4 (2)	C18—C19—O3—C20	10.7 (3)
C3—C13—C14—C15	143.95 (15)	C14—C19—O3—C20	−167.11 (16)
O1—C13—C14—C19	145.16 (17)	C21—C20—O3—C19	171.34 (17)
C3—C13—C14—C19	−36.5 (2)	C25—C24—O4—C23	−56.2 (3)
C19—C14—C15—C16	1.0 (3)	C29—C24—O4—C23	128.2 (2)
C13—C14—C15—C16	−179.46 (16)	C22—C23—O4—C24	157.44 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	1.96	2.8105 (17)	170
C26—H26···Cg4ii	0.93	2.91	3.617 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	1.96	2.8105 (17)	170
C26—H26⋯Cg4ii	0.93	2.91	3.617 (3)	134

Symmetry codes: (i) ; (ii) .