Ethyl 27-oxo-15-oxa-2,20-diaza-hexa-cyclo-[18.6.1.0(1,8).0(2,6).0(9,14).0(21,26)]hepta-cosa-9,11,13,21,23,25-hexa-ene-7-carboxyl-ate.

In the title compound, C27H30N2O4, the pyrrolidine ring adopts a twisted conformation. The indoline ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 81.7 (8)°. In the crystal, mol-ecules are linked into centrosymmetric dimers with graph-set motif R2(2)(16) via pairs of C-H⋯O hydrogen bonds. The terminal ethyl group of the ester group is disordered over two sets of sites, with a site-occupancy ratio of 0.587 (11):0.413 (11).

Related literature

For the biological activity of spiro-pyrrolidine derivatives, see: Obniska et al. (2003 ▶); Peddi et al. (2004 ▶); Christoph et al. (2011 ▶); Stylianakis et al. (2003 ▶); Waldmann (1995 ▶); Suzuki et al. (1994 ▶); Huryn et al. (1991 ▶). For a related structure, see: Ganesh et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: Nardelli et al. (1983 ▶).

Experimental

Crystal data

C27H30N2O4

M = 446.53

Triclinic,

a = 8.9327 (5) Å

b = 10.0068 (5) Å

c = 14.6379 (11) Å

α = 103.988 (4)°

β = 95.023 (4)°

γ = 113.775 (3)°

V = 1136.41 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.974, T max = 0.978

20472 measured reflections

5603 independent reflections

4378 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.08

5603 reflections

319 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 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/S1600536812049082/bt6853sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049082/bt6853Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049082/bt6853Isup3.cml

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

C27H30N2O4	Z = 2
Mr = 446.53	F(000) = 476
Triclinic, P1	Dx = 1.305 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9327 (5) Å	Cell parameters from 5603 reflections
b = 10.0068 (5) Å	θ = 1.5–28.3°
c = 14.6379 (11) Å	µ = 0.09 mm−1
α = 103.988 (4)°	T = 293 K
β = 95.023 (4)°	Block, white crystalline
γ = 113.775 (3)°	0.30 × 0.30 × 0.25 mm
V = 1136.41 (13) Å3

Bruker APEXII CCD area-detector diffractometer	5603 independent reflections
Radiation source: fine-focus sealed tube	4378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.974, Tmax = 0.978	k = −13→13
20472 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.215P] where P = (Fo2 + 2Fc2)/3
5603 reflections	(Δ/σ)max = 0.002
319 parameters	Δρmax = 0.23 e Å−3
40 restraints	Δρmin = −0.22 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	Occ. (<1)
C1A	−0.0430 (10)	1.0338 (8)	0.2839 (4)	0.0877 (18)	0.587 (11)
H1A1	0.0125	1.0358	0.2306	0.132*	0.587 (11)
H1A2	−0.0730	1.1174	0.2975	0.132*	0.587 (11)
H1A3	−0.1420	0.9386	0.2680	0.132*	0.587 (11)
C2A	0.0677 (12)	1.0483 (8)	0.3675 (6)	0.089 (3)	0.587 (11)
H2A1	0.0188	1.0599	0.4238	0.106*	0.587 (11)
H2A2	0.1740	1.1376	0.3795	0.106*	0.587 (11)
C1B	0.0656 (17)	1.0966 (9)	0.2980 (6)	0.088 (3)	0.413 (11)
H1B1	0.1845	1.1562	0.3183	0.131*	0.413 (11)
H1B2	0.0130	1.1639	0.3003	0.131*	0.413 (11)
H1B3	0.0393	1.0304	0.2334	0.131*	0.413 (11)
C2B	0.0054 (13)	1.0057 (11)	0.3611 (9)	0.072 (3)	0.413 (11)
H2B1	−0.1149	0.9451	0.3426	0.086*	0.413 (11)
H2B2	0.0346	1.0696	0.4274	0.086*	0.413 (11)
C3	0.21727 (18)	0.92280 (15)	0.41102 (10)	0.0423 (3)
C4	0.26073 (15)	0.78973 (13)	0.38728 (9)	0.0328 (3)
H4	0.3792	0.8281	0.4159	0.039*
C5	0.15967 (15)	0.66458 (14)	0.43037 (9)	0.0346 (3)
H5	0.0410	0.6419	0.4175	0.042*
C6	0.22279 (18)	0.69639 (17)	0.53715 (10)	0.0466 (3)
H6A	0.2708	0.8051	0.5713	0.056*
H6B	0.1334	0.6416	0.5664	0.056*
C7	0.3552 (2)	0.63749 (19)	0.53718 (11)	0.0550 (4)
H7A	0.4601	0.7115	0.5293	0.066*
H7B	0.3743	0.6130	0.5960	0.066*
C8	0.2771 (2)	0.49510 (18)	0.45101 (11)	0.0503 (4)
H8A	0.3628	0.4711	0.4251	0.060*
H8B	0.2022	0.4082	0.4687	0.060*
C9	0.24212 (14)	0.55059 (13)	0.28972 (9)	0.0314 (2)
C10	0.40719 (14)	0.54634 (14)	0.28034 (9)	0.0335 (3)
C11	0.56843 (16)	0.64768 (16)	0.32716 (11)	0.0433 (3)
H11	0.5907	0.7389	0.3736	0.052*
C12	0.69804 (17)	0.6109 (2)	0.30370 (12)	0.0531 (4)
H12	0.8079	0.6793	0.3342	0.064*
C13	0.66598 (19)	0.4754 (2)	0.23631 (12)	0.0552 (4)
H13	0.7541	0.4521	0.2231	0.066*
C14	0.50416 (19)	0.37281 (19)	0.18772 (11)	0.0491 (4)
H14	0.4821	0.2810	0.1419	0.059*
C15	0.37664 (16)	0.41162 (15)	0.20968 (9)	0.0373 (3)
C16	0.11869 (15)	0.40657 (14)	0.20770 (9)	0.0362 (3)
C17	0.1341 (2)	0.19559 (16)	0.08382 (11)	0.0528 (4)
H17A	0.0135	0.1469	0.0769	0.063*
H17B	0.1753	0.1226	0.0927	0.063*
C18	0.1747 (2)	0.23314 (18)	−0.00835 (11)	0.0552 (4)
H18A	0.1372	0.1376	−0.0597	0.066*
H18B	0.2953	0.2869	0.0004	0.066*
C19	0.0979 (2)	0.33016 (19)	−0.04075 (11)	0.0568 (4)
H19A	0.0621	0.2915	−0.1103	0.068*
H19B	−0.0013	0.3154	−0.0142	0.068*
C20	0.2087 (2)	0.49895 (18)	−0.01325 (10)	0.0531 (4)
H20A	0.3192	0.5157	−0.0248	0.064*
H20B	0.1635	0.5445	−0.0528	0.064*
C21	0.33250 (17)	0.72236 (15)	0.12529 (10)	0.0396 (3)
C22	0.4290 (2)	0.80905 (19)	0.07220 (11)	0.0536 (4)
H22	0.4166	0.7651	0.0066	0.064*
C23	0.5431 (2)	0.95975 (19)	0.11637 (12)	0.0592 (4)
H23	0.6082	1.0165	0.0806	0.071*
C24	0.5606 (2)	1.02605 (18)	0.21268 (12)	0.0565 (4)
H24	0.6379	1.1274	0.2427	0.068*
C25	0.46165 (18)	0.94020 (16)	0.26501 (11)	0.0473 (3)
H25	0.4736	0.9863	0.3302	0.057*
C26	0.34589 (15)	0.78868 (14)	0.22383 (9)	0.0350 (3)
C27	0.23201 (14)	0.69994 (13)	0.28114 (8)	0.0314 (2)
H27	0.1165	0.6710	0.2510	0.038*
N1	0.18398 (13)	0.53096 (12)	0.37981 (7)	0.0361 (2)
N2	0.20527 (14)	0.32851 (12)	0.16915 (8)	0.0398 (3)
O1	0.28603 (18)	1.03033 (14)	0.48165 (9)	0.0743 (4)
O2	0.09278 (16)	0.90670 (14)	0.34755 (9)	0.0684 (3)
O3	0.22133 (12)	0.57163 (11)	0.08703 (6)	0.0447 (2)
O4	−0.03046 (11)	0.36456 (11)	0.18380 (7)	0.0494 (3)

	U11	U22	U33	U12	U13	U23
C1A	0.106 (4)	0.079 (3)	0.104 (3)	0.063 (3)	0.008 (3)	0.038 (3)
C2A	0.119 (6)	0.077 (4)	0.087 (4)	0.078 (4)	−0.009 (4)	0.002 (3)
C1B	0.131 (7)	0.069 (4)	0.074 (4)	0.046 (4)	0.027 (4)	0.032 (3)
C2B	0.092 (5)	0.072 (4)	0.087 (6)	0.058 (4)	0.041 (5)	0.038 (4)
C3	0.0498 (7)	0.0370 (7)	0.0411 (8)	0.0205 (6)	0.0135 (6)	0.0094 (6)
C4	0.0343 (6)	0.0329 (6)	0.0297 (6)	0.0152 (5)	0.0065 (5)	0.0064 (5)
C5	0.0346 (6)	0.0354 (6)	0.0328 (6)	0.0155 (5)	0.0097 (5)	0.0072 (5)
C6	0.0565 (8)	0.0451 (8)	0.0320 (7)	0.0163 (6)	0.0131 (6)	0.0103 (6)
C7	0.0570 (9)	0.0661 (10)	0.0420 (8)	0.0227 (8)	0.0038 (7)	0.0265 (7)
C8	0.0655 (9)	0.0601 (9)	0.0476 (9)	0.0391 (8)	0.0218 (7)	0.0304 (7)
C9	0.0315 (5)	0.0331 (6)	0.0300 (6)	0.0157 (5)	0.0067 (5)	0.0075 (5)
C10	0.0341 (6)	0.0377 (6)	0.0340 (6)	0.0193 (5)	0.0086 (5)	0.0128 (5)
C11	0.0360 (6)	0.0470 (8)	0.0474 (8)	0.0183 (6)	0.0062 (6)	0.0162 (6)
C12	0.0349 (7)	0.0702 (10)	0.0638 (10)	0.0254 (7)	0.0118 (7)	0.0319 (9)
C13	0.0528 (8)	0.0895 (12)	0.0568 (10)	0.0507 (9)	0.0274 (7)	0.0396 (9)
C14	0.0629 (9)	0.0646 (9)	0.0431 (8)	0.0460 (8)	0.0218 (7)	0.0208 (7)
C15	0.0433 (7)	0.0437 (7)	0.0347 (7)	0.0255 (6)	0.0126 (5)	0.0156 (5)
C16	0.0379 (6)	0.0353 (6)	0.0342 (7)	0.0161 (5)	0.0082 (5)	0.0081 (5)
C17	0.0673 (9)	0.0375 (7)	0.0460 (9)	0.0239 (7)	0.0076 (7)	−0.0002 (6)
C18	0.0703 (10)	0.0500 (9)	0.0403 (8)	0.0310 (8)	0.0085 (7)	−0.0018 (7)
C19	0.0667 (10)	0.0619 (10)	0.0342 (8)	0.0330 (8)	−0.0024 (7)	−0.0020 (7)
C20	0.0743 (10)	0.0599 (9)	0.0305 (7)	0.0375 (8)	0.0112 (7)	0.0090 (6)
C21	0.0473 (7)	0.0439 (7)	0.0353 (7)	0.0260 (6)	0.0094 (6)	0.0148 (6)
C22	0.0738 (10)	0.0600 (9)	0.0394 (8)	0.0345 (8)	0.0225 (7)	0.0230 (7)
C23	0.0705 (10)	0.0612 (10)	0.0576 (10)	0.0276 (8)	0.0278 (8)	0.0351 (8)
C24	0.0612 (9)	0.0471 (8)	0.0554 (10)	0.0138 (7)	0.0143 (8)	0.0226 (7)
C25	0.0530 (8)	0.0448 (8)	0.0388 (8)	0.0155 (6)	0.0103 (6)	0.0140 (6)
C26	0.0392 (6)	0.0386 (6)	0.0322 (6)	0.0201 (5)	0.0081 (5)	0.0134 (5)
C27	0.0331 (6)	0.0327 (6)	0.0287 (6)	0.0164 (5)	0.0046 (5)	0.0072 (5)
N1	0.0436 (6)	0.0373 (6)	0.0323 (6)	0.0210 (5)	0.0125 (4)	0.0115 (4)
N2	0.0451 (6)	0.0357 (6)	0.0365 (6)	0.0207 (5)	0.0071 (5)	0.0024 (4)
O1	0.0918 (9)	0.0525 (7)	0.0627 (8)	0.0368 (7)	0.0019 (7)	−0.0139 (6)
O2	0.0874 (8)	0.0622 (7)	0.0668 (8)	0.0558 (7)	−0.0023 (6)	0.0045 (6)
O3	0.0589 (6)	0.0458 (5)	0.0286 (5)	0.0243 (5)	0.0090 (4)	0.0078 (4)
O4	0.0336 (5)	0.0502 (6)	0.0515 (6)	0.0142 (4)	0.0025 (4)	0.0029 (5)

C1A—C2A	1.443 (6)	C11—C12	1.3947 (19)
C1A—H1A1	0.9600	C11—H11	0.9300
C1A—H1A2	0.9600	C12—C13	1.373 (2)
C1A—H1A3	0.9600	C12—H12	0.9300
C2A—O2	1.487 (5)	C13—C14	1.385 (2)
C2A—H2A1	0.9700	C13—H13	0.9300
C2A—H2A2	0.9700	C14—C15	1.3827 (18)
C1B—C2B	1.438 (7)	C14—H14	0.9300
C1B—H1B1	0.9600	C15—N2	1.4011 (17)
C1B—H1B2	0.9600	C16—O4	1.2123 (15)
C1B—H1B3	0.9600	C16—N2	1.3701 (16)
C2B—O2	1.478 (6)	C17—N2	1.4524 (18)
C2B—H2B1	0.9700	C17—C18	1.521 (2)
C2B—H2B2	0.9700	C17—H17A	0.9700
C3—O1	1.1925 (18)	C17—H17B	0.9700
C3—O2	1.3145 (18)	C18—C19	1.530 (2)
C3—C4	1.5038 (17)	C18—H18A	0.9700
C4—C5	1.5333 (16)	C18—H18B	0.9700
C4—C27	1.5351 (17)	C19—C20	1.500 (2)
C4—H4	0.9800	C19—H19A	0.9700
C5—N1	1.4720 (16)	C19—H19B	0.9700
C5—C6	1.5241 (19)	C20—O3	1.4440 (16)
C5—H5	0.9800	C20—H20A	0.9700
C6—C7	1.520 (2)	C20—H20B	0.9700
C6—H6A	0.9700	C21—O3	1.3643 (16)
C6—H6B	0.9700	C21—C22	1.3930 (19)
C7—C8	1.511 (2)	C21—C26	1.4064 (18)
C7—H7A	0.9700	C22—C23	1.380 (2)
C7—H7B	0.9700	C22—H22	0.9300
C8—N1	1.4756 (17)	C23—C24	1.370 (2)
C8—H8A	0.9700	C23—H23	0.9300
C8—H8B	0.9700	C24—C25	1.3896 (19)
C9—N1	1.4867 (15)	C24—H24	0.9300
C9—C10	1.5093 (15)	C25—C26	1.3843 (19)
C9—C16	1.5442 (17)	C25—H25	0.9300
C9—C27	1.5669 (16)	C26—C27	1.5194 (16)
C10—C11	1.3734 (18)	C27—H27	0.9800
C10—C15	1.3934 (18)
C1A—C2A—O2	107.4 (5)	C14—C13—H13	119.5
C1A—C2A—H2A1	110.2	C15—C14—C13	117.71 (14)
O2—C2A—H2A1	110.2	C15—C14—H14	121.1
C1A—C2A—H2A2	110.2	C13—C14—H14	121.1
O2—C2A—H2A2	110.2	C14—C15—C10	121.80 (13)
H2A1—C2A—H2A2	108.5	C14—C15—N2	127.97 (13)
C2B—C1B—H1B1	109.5	C10—C15—N2	110.23 (10)
C2B—C1B—H1B2	109.5	O4—C16—N2	125.24 (12)
H1B1—C1B—H1B2	109.5	O4—C16—C9	126.60 (11)
C2B—C1B—H1B3	109.5	N2—C16—C9	108.07 (10)
H1B1—C1B—H1B3	109.5	N2—C17—C18	113.75 (12)
H1B2—C1B—H1B3	109.5	N2—C17—H17A	108.8
C1B—C2B—O2	103.0 (6)	C18—C17—H17A	108.8
C1B—C2B—H2B1	111.2	N2—C17—H17B	108.8
O2—C2B—H2B1	111.2	C18—C17—H17B	108.8
C1B—C2B—H2B2	111.2	H17A—C17—H17B	107.7
O2—C2B—H2B2	111.2	C17—C18—C19	115.73 (13)
H2B1—C2B—H2B2	109.1	C17—C18—H18A	108.3
O1—C3—O2	123.36 (13)	C19—C18—H18A	108.3
O1—C3—C4	123.34 (14)	C17—C18—H18B	108.3
O2—C3—C4	113.27 (12)	C19—C18—H18B	108.3
C3—C4—C5	111.85 (10)	H18A—C18—H18B	107.4
C3—C4—C27	118.71 (10)	C20—C19—C18	116.20 (14)
C5—C4—C27	102.81 (9)	C20—C19—H19A	108.2
C3—C4—H4	107.6	C18—C19—H19A	108.2
C5—C4—H4	107.6	C20—C19—H19B	108.2
C27—C4—H4	107.6	C18—C19—H19B	108.2
N1—C5—C6	105.91 (10)	H19A—C19—H19B	107.4
N1—C5—C4	103.94 (9)	O3—C20—C19	110.62 (13)
C6—C5—C4	115.22 (11)	O3—C20—H20A	109.5
N1—C5—H5	110.5	C19—C20—H20A	109.5
C6—C5—H5	110.5	O3—C20—H20B	109.5
C4—C5—H5	110.5	C19—C20—H20B	109.5
C7—C6—C5	103.05 (11)	H20A—C20—H20B	108.1
C7—C6—H6A	111.2	O3—C21—C22	123.50 (13)
C5—C6—H6A	111.2	O3—C21—C26	116.04 (11)
C7—C6—H6B	111.2	C22—C21—C26	120.46 (13)
C5—C6—H6B	111.2	C23—C22—C21	120.37 (14)
H6A—C6—H6B	109.1	C23—C22—H22	119.8
C8—C7—C6	102.04 (12)	C21—C22—H22	119.8
C8—C7—H7A	111.4	C24—C23—C22	120.23 (14)
C6—C7—H7A	111.4	C24—C23—H23	119.9
C8—C7—H7B	111.4	C22—C23—H23	119.9
C6—C7—H7B	111.4	C23—C24—C25	119.26 (15)
H7A—C7—H7B	109.2	C23—C24—H24	120.4
N1—C8—C7	105.66 (11)	C25—C24—H24	120.4
N1—C8—H8A	110.6	C26—C25—C24	122.54 (14)
C7—C8—H8A	110.6	C26—C25—H25	118.7
N1—C8—H8B	110.6	C24—C25—H25	118.7
C7—C8—H8B	110.6	C25—C26—C21	117.12 (12)
H8A—C8—H8B	108.7	C25—C26—C27	121.56 (11)
N1—C9—C10	116.46 (9)	C21—C26—C27	121.25 (11)
N1—C9—C16	106.22 (9)	C26—C27—C4	114.73 (10)
C10—C9—C16	101.89 (9)	C26—C27—C9	117.37 (9)
N1—C9—C27	104.52 (9)	C4—C27—C9	101.60 (9)
C10—C9—C27	115.18 (9)	C26—C27—H27	107.5
C16—C9—C27	112.44 (9)	C4—C27—H27	107.5
C11—C10—C15	119.80 (11)	C9—C27—H27	107.5
C11—C10—C9	131.67 (12)	C5—N1—C8	108.13 (10)
C15—C10—C9	108.54 (10)	C5—N1—C9	110.23 (9)
C10—C11—C12	118.65 (14)	C8—N1—C9	120.66 (10)
C10—C11—H11	120.7	C16—N2—C15	110.85 (10)
C12—C11—H11	120.7	C16—N2—C17	123.63 (11)
C13—C12—C11	121.05 (14)	C15—N2—C17	124.23 (11)
C13—C12—H12	119.5	C3—O2—C2B	124.6 (5)
C11—C12—H12	119.5	C3—O2—C2A	111.3 (3)
C12—C13—C14	120.93 (13)	C21—O3—C20	117.33 (11)
C12—C13—H13	119.5
O1—C3—C4—C5	89.09 (17)	C22—C21—C26—C27	175.06 (12)
O2—C3—C4—C5	−89.09 (14)	C25—C26—C27—C4	−2.05 (16)
O1—C3—C4—C27	−151.44 (14)	C21—C26—C27—C4	−178.96 (10)
O2—C3—C4—C27	30.38 (16)	C25—C26—C27—C9	−121.25 (13)
C3—C4—C5—N1	165.51 (10)	C21—C26—C27—C9	61.84 (15)
C27—C4—C5—N1	37.05 (11)	C3—C4—C27—C26	67.92 (14)
C3—C4—C5—C6	−79.07 (14)	C5—C4—C27—C26	−168.04 (9)
C27—C4—C5—C6	152.47 (10)	C3—C4—C27—C9	−164.39 (10)
N1—C5—C6—C7	28.37 (13)	C5—C4—C27—C9	−40.35 (11)
C4—C5—C6—C7	−85.91 (13)	N1—C9—C27—C26	155.06 (10)
C5—C6—C7—C8	−38.37 (13)	C10—C9—C27—C26	25.97 (15)
C6—C7—C8—N1	34.89 (14)	C16—C9—C27—C26	−90.16 (12)
N1—C9—C10—C11	−70.23 (17)	N1—C9—C27—C4	29.09 (11)
C16—C9—C10—C11	174.70 (13)	C10—C9—C27—C4	−99.99 (11)
C27—C9—C10—C11	52.69 (18)	C16—C9—C27—C4	143.88 (10)
N1—C9—C10—C15	110.05 (12)	C6—C5—N1—C8	−6.82 (13)
C16—C9—C10—C15	−5.02 (12)	C4—C5—N1—C8	115.00 (11)
C27—C9—C10—C15	−127.02 (11)	C6—C5—N1—C9	−140.65 (10)
C15—C10—C11—C12	−1.28 (19)	C4—C5—N1—C9	−18.83 (12)
C9—C10—C11—C12	179.03 (12)	C7—C8—N1—C5	−17.71 (14)
C10—C11—C12—C13	−1.0 (2)	C7—C8—N1—C9	110.39 (13)
C11—C12—C13—C14	1.7 (2)	C10—C9—N1—C5	121.72 (11)
C12—C13—C14—C15	−0.2 (2)	C16—C9—N1—C5	−125.67 (10)
C13—C14—C15—C10	−2.1 (2)	C27—C9—N1—C5	−6.59 (12)
C13—C14—C15—N2	178.71 (13)	C10—C9—N1—C8	−5.43 (16)
C11—C10—C15—C14	2.89 (19)	C16—C9—N1—C8	107.18 (12)
C9—C10—C15—C14	−177.35 (11)	C27—C9—N1—C8	−133.74 (11)
C11—C10—C15—N2	−177.82 (11)	O4—C16—N2—C15	177.33 (12)
C9—C10—C15—N2	1.94 (14)	C9—C16—N2—C15	−5.83 (14)
N1—C9—C16—O4	60.93 (16)	O4—C16—N2—C17	9.9 (2)
C10—C9—C16—O4	−176.69 (13)	C9—C16—N2—C17	−173.31 (12)
C27—C9—C16—O4	−52.82 (17)	C14—C15—N2—C16	−178.20 (13)
N1—C9—C16—N2	−115.86 (10)	C10—C15—N2—C16	2.56 (15)
C10—C9—C16—N2	6.52 (12)	C14—C15—N2—C17	−10.8 (2)
C27—C9—C16—N2	130.40 (10)	C10—C15—N2—C17	169.95 (12)
N2—C17—C18—C19	−66.50 (18)	C18—C17—N2—C16	96.75 (16)
C17—C18—C19—C20	97.32 (18)	C18—C17—N2—C15	−69.06 (18)
C18—C19—C20—O3	−76.86 (17)	O1—C3—O2—C2B	−9.2 (4)
O3—C21—C22—C23	−177.87 (14)	C4—C3—O2—C2B	169.0 (4)
C26—C21—C22—C23	2.2 (2)	O1—C3—O2—C2A	8.6 (5)
C21—C22—C23—C24	−0.9 (3)	C4—C3—O2—C2A	−173.2 (5)
C22—C23—C24—C25	−0.4 (3)	C1B—C2B—O2—C3	106.8 (10)
C23—C24—C25—C26	0.6 (2)	C1B—C2B—O2—C2A	52.4 (13)
C24—C25—C26—C21	0.6 (2)	C1A—C2A—O2—C3	167.2 (7)
C24—C25—C26—C27	−176.39 (13)	C1A—C2A—O2—C2B	−58.7 (15)
O3—C21—C26—C25	178.04 (12)	C22—C21—O3—C20	1.99 (19)
C22—C21—C26—C25	−1.99 (19)	C26—C21—O3—C20	−178.03 (11)
O3—C21—C26—C27	−4.92 (17)	C19—C20—O3—C21	173.01 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.49	3.3957 (19)	164
C12—H12···O2ii	0.93	2.59	3.446 (2)	153
C13—H13···O4ii	0.93	2.47	3.3986 (17)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.49	3.3957 (19)	164
C12—H12⋯O2ii	0.93	2.59	3.446 (2)	153
C13—H13⋯O4ii	0.93	2.47	3.3986 (17)	175

Symmetry codes: (i) ; (ii) .