3-(2,5-Di-methyl-phen-yl)-8-meth-oxy-2-oxo-1-aza-spiro-[4.5]dec-3-en-4-yl 3-(2-bromo-4-fluoro-phen-yl)acrylate.

In the title compound, C27H27BrFNO4, which is an inhibitor of acetyl-CoA carboxyl-ase, the cyclo-hexane ring displays a chair comformation with the spiro-C and meth-oxy-bearing C atoms deviating by 0.681 (7) and -0.655 (1) Å, resppectively, from the mean plane formed by the other four C atoms of the spiro-C6 ring. The mean planes of the cyclo-hexane and 2-bromo-4-fluoro-phenyl rings are nearly perpendicular to that of the pyrrolidine ring, making dihedral angles 89.75 (6) and 87.60 (9)°, respectively. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the pesticide spiro­tetra­mat (systematic name: cis-3-(2,5-di­methyl­phen­yl)-8-meth­oxy-2-oxo-1-aza­spiro­[4.5]dec-3-en-4-yl ethyl carbonate), the central unit of the title compound, see: Fischer & Weiss (2008 ▶); Maus (2008 ▶). For structures of spiro­tetra­mat derivatives, see: Fischer et al. (2010 ▶); Campbell et al. (1985 ▶); Schobert & Schlenk (2008 ▶); Zhao et al. (2012 ▶); Wang et al. (2011 ▶). For the metabolic transformation of spiro­tetra­mat, see: Bruck et al. (2009 ▶).

Experimental

Crystal data

C27H27BrFNO4

M = 528.41

Triclinic,

a = 10.5170 (5) Å

b = 11.2410 (6) Å

c = 12.5150 (7) Å

α = 110.364 (2)°

β = 102.049 (2)°

γ = 107.409 (1)°

V = 1239.95 (11) Å3

Z = 2

Mo Kα radiation

μ = 1.70 mm−1

T = 296 K

0.48 × 0.45 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.446, T max = 0.665

10805 measured reflections

4845 independent reflections

3433 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.134

S = 1.00

4845 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.95 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); 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: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301430X/vm2194sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301430X/vm2194Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301430X/vm2194Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301430X/vm2194Isup4.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301430X/vm2194Isup5.cml

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

C27H27BrFNO4	Z = 2
Mr = 528.41	F(000) = 544
Triclinic, P1	Dx = 1.415 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5170 (5) Å	Cell parameters from 8334 reflections
b = 11.2410 (6) Å	θ = 3.1–27.4°
c = 12.5150 (7) Å	µ = 1.70 mm−1
α = 110.364 (2)°	T = 296 K
β = 102.049 (2)°	Chunk, colorless
γ = 107.409 (1)°	0.48 × 0.45 × 0.24 mm
V = 1239.95 (11) Å3

Rigaku R-AXIS RAPID/ZJUG diffractometer	4845 independent reflections
Radiation source: rotating anode	3433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 10.00 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.446, Tmax = 0.665	l = −15→15
10805 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0452P)2 + 2.4533P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4845 reflections	Δρmax = 0.46 e Å−3
311 parameters	Δρmin = −0.95 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (2)

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	0.8088 (4)	0.4745 (4)	0.4082 (4)	0.0461 (9)
C2	0.6693 (4)	0.4235 (4)	0.3104 (4)	0.0427 (9)
C3	0.5971 (4)	0.2940 (4)	0.2902 (3)	0.0383 (8)
C4	0.6755 (4)	0.2431 (4)	0.3664 (3)	0.0368 (8)
C5	0.6237 (4)	0.5058 (4)	0.2510 (4)	0.0478 (10)
C6	0.7037 (5)	0.5696 (4)	0.1946 (4)	0.0517 (10)
C7	0.6475 (6)	0.6406 (5)	0.1396 (4)	0.0634 (13)
H7	0.6991	0.6852	0.1026	0.076*
C8	0.5196 (6)	0.6467 (5)	0.1384 (4)	0.0648 (13)
H8	0.4867	0.6957	0.1012	0.078*
C9	0.4375 (5)	0.5814 (4)	0.1916 (4)	0.0538 (11)
C10	0.4938 (4)	0.5121 (4)	0.2489 (4)	0.0489 (10)
H10	0.4422	0.4689	0.2868	0.059*
C11	0.8437 (6)	0.5624 (6)	0.1891 (6)	0.0758 (15)
H11A	0.9195	0.6344	0.2621	0.114*
H11B	0.8595	0.5745	0.1200	0.114*
H11C	0.8408	0.4736	0.1816	0.114*
C12	0.2922 (5)	0.5783 (6)	0.1840 (5)	0.0744 (15)
H12A	0.2922	0.6668	0.1937	0.112*
H12B	0.2672	0.5584	0.2473	0.112*
H12C	0.2241	0.5075	0.1063	0.112*
C13	0.4365 (4)	0.1713 (4)	0.0883 (3)	0.0392 (8)
C14	0.2895 (4)	0.1370 (4)	0.0199 (3)	0.0389 (8)
H14	0.2559	0.0845	−0.0640	0.047*
C15	0.2014 (4)	0.1765 (4)	0.0705 (3)	0.0368 (8)
H15	0.2330	0.2179	0.1551	0.044*
C16	0.0597 (4)	0.1620 (4)	0.0080 (3)	0.0368 (8)
C17	−0.0245 (4)	0.2068 (4)	0.0720 (3)	0.0375 (8)
C18	−0.1587 (4)	0.1930 (4)	0.0134 (4)	0.0433 (9)
H18	−0.2139	0.2221	0.0571	0.052*
C19	−0.2076 (4)	0.1352 (4)	−0.1108 (4)	0.0450 (9)
C20	−0.1310 (4)	0.0910 (4)	−0.1794 (4)	0.0498 (10)
H20	−0.1671	0.0532	−0.2639	0.060*
C21	0.0027 (4)	0.1043 (4)	−0.1186 (4)	0.0448 (9)
H21	0.0561	0.0738	−0.1637	0.054*
C22	0.7009 (4)	0.1194 (4)	0.2883 (3)	0.0369 (8)
H22A	0.6100	0.0438	0.2336	0.044*
H22B	0.7531	0.1460	0.2391	0.044*
C23	0.7841 (4)	0.0692 (4)	0.3654 (3)	0.0416 (9)
H23A	0.7944	−0.0113	0.3124	0.050*
H23B	0.8785	0.1417	0.4148	0.050*
C24	0.7083 (4)	0.0313 (4)	0.4473 (3)	0.0422 (9)
H24	0.6171	−0.0484	0.3967	0.051*
C25	0.6811 (4)	0.1511 (4)	0.5247 (4)	0.0478 (10)
H25A	0.7713	0.2267	0.5811	0.057*
H25B	0.6272	0.1222	0.5720	0.057*
C26	0.5993 (4)	0.2028 (4)	0.4484 (4)	0.0446 (9)
H26A	0.5887	0.2827	0.5019	0.054*
H26B	0.5050	0.1305	0.3983	0.054*
C27	0.7981 (6)	−0.1319 (5)	0.4762 (5)	0.0770 (16)
H27A	0.7041	−0.2030	0.4282	0.115*
H27B	0.8414	−0.1527	0.5390	0.115*
H27C	0.8543	−0.1281	0.4251	0.115*
N1	0.8079 (3)	0.3695 (3)	0.4373 (3)	0.0448 (8)
H1	0.8779	0.3758	0.4920	0.054*
O1	0.9056 (3)	0.5907 (3)	0.4548 (3)	0.0610 (9)
O2	0.7899 (3)	−0.0026 (3)	0.5295 (3)	0.0570 (8)
O3	0.4596 (2)	0.2081 (3)	0.2103 (2)	0.0393 (6)
O4	0.5294 (3)	0.1721 (3)	0.0476 (3)	0.0579 (8)
F1	−0.3399 (2)	0.1198 (3)	−0.1697 (3)	0.0642 (7)
Br1	0.04050 (4)	0.28752 (5)	0.24507 (4)	0.0578 (2)

	U11	U22	U33	U12	U13	U23
C1	0.037 (2)	0.041 (2)	0.049 (2)	0.0123 (17)	0.0039 (17)	0.0168 (19)
C2	0.036 (2)	0.042 (2)	0.043 (2)	0.0138 (16)	0.0015 (16)	0.0204 (18)
C3	0.0278 (17)	0.041 (2)	0.039 (2)	0.0122 (15)	0.0059 (14)	0.0151 (17)
C4	0.0283 (18)	0.0381 (19)	0.037 (2)	0.0086 (14)	0.0044 (14)	0.0163 (16)
C5	0.045 (2)	0.037 (2)	0.044 (2)	0.0096 (16)	−0.0010 (17)	0.0142 (18)
C6	0.060 (3)	0.040 (2)	0.048 (2)	0.0157 (19)	0.014 (2)	0.0195 (19)
C7	0.080 (3)	0.050 (3)	0.054 (3)	0.018 (2)	0.016 (2)	0.028 (2)
C8	0.075 (3)	0.049 (3)	0.059 (3)	0.023 (2)	0.002 (2)	0.026 (2)
C9	0.060 (3)	0.042 (2)	0.047 (2)	0.021 (2)	−0.001 (2)	0.016 (2)
C10	0.048 (2)	0.040 (2)	0.050 (2)	0.0134 (17)	0.0057 (18)	0.0190 (19)
C11	0.076 (4)	0.077 (4)	0.091 (4)	0.031 (3)	0.042 (3)	0.047 (3)
C12	0.071 (3)	0.067 (3)	0.082 (4)	0.037 (3)	0.007 (3)	0.033 (3)
C13	0.0295 (19)	0.041 (2)	0.042 (2)	0.0128 (15)	0.0072 (15)	0.0181 (17)
C14	0.0355 (19)	0.041 (2)	0.0323 (19)	0.0132 (15)	0.0068 (15)	0.0132 (16)
C15	0.0328 (18)	0.043 (2)	0.0289 (18)	0.0108 (15)	0.0071 (14)	0.0157 (16)
C16	0.0298 (18)	0.0363 (19)	0.041 (2)	0.0090 (14)	0.0090 (14)	0.0187 (16)
C17	0.0363 (19)	0.0359 (19)	0.036 (2)	0.0109 (15)	0.0118 (15)	0.0151 (16)
C18	0.035 (2)	0.041 (2)	0.057 (3)	0.0176 (16)	0.0194 (17)	0.0208 (19)
C19	0.0293 (19)	0.047 (2)	0.059 (3)	0.0141 (16)	0.0085 (17)	0.029 (2)
C20	0.043 (2)	0.058 (3)	0.042 (2)	0.0150 (19)	0.0043 (17)	0.026 (2)
C21	0.036 (2)	0.055 (2)	0.039 (2)	0.0165 (17)	0.0084 (16)	0.0203 (19)
C22	0.0361 (19)	0.040 (2)	0.0355 (19)	0.0161 (15)	0.0134 (15)	0.0172 (16)
C23	0.041 (2)	0.044 (2)	0.040 (2)	0.0190 (17)	0.0126 (16)	0.0176 (17)
C24	0.046 (2)	0.046 (2)	0.033 (2)	0.0185 (17)	0.0075 (16)	0.0181 (17)
C25	0.053 (2)	0.055 (2)	0.040 (2)	0.0229 (19)	0.0172 (18)	0.0237 (19)
C26	0.043 (2)	0.052 (2)	0.044 (2)	0.0228 (18)	0.0163 (17)	0.0226 (19)
C27	0.109 (4)	0.055 (3)	0.068 (3)	0.046 (3)	0.015 (3)	0.027 (3)
N1	0.0353 (17)	0.0384 (17)	0.0474 (19)	0.0095 (13)	−0.0018 (14)	0.0183 (15)
O1	0.0406 (16)	0.0398 (16)	0.076 (2)	0.0051 (13)	−0.0066 (14)	0.0217 (15)
O2	0.080 (2)	0.0511 (17)	0.0417 (16)	0.0353 (16)	0.0093 (14)	0.0224 (14)
O3	0.0250 (12)	0.0469 (15)	0.0410 (14)	0.0099 (10)	0.0051 (10)	0.0214 (12)
O4	0.0389 (16)	0.082 (2)	0.0533 (18)	0.0284 (15)	0.0198 (13)	0.0247 (16)
F1	0.0347 (12)	0.0731 (17)	0.0796 (18)	0.0215 (11)	0.0030 (11)	0.0380 (15)
Br1	0.0467 (3)	0.0738 (4)	0.0435 (3)	0.0204 (2)	0.01813 (19)	0.0176 (2)

C1—O1	1.228 (5)	C15—C16	1.463 (5)
C1—N1	1.350 (5)	C15—H15	0.9300
C1—C2	1.496 (5)	C16—C21	1.395 (5)
C2—C3	1.327 (5)	C16—C17	1.401 (5)
C2—C5	1.494 (5)	C17—C18	1.383 (5)
C3—O3	1.383 (4)	C17—Br1	1.903 (4)
C3—C4	1.500 (5)	C18—C19	1.367 (6)
C4—N1	1.473 (4)	C18—H18	0.9300
C4—C26	1.533 (5)	C19—F1	1.359 (4)
C4—C22	1.532 (5)	C19—C20	1.366 (6)
C5—C10	1.385 (6)	C20—C21	1.388 (5)
C5—C6	1.400 (6)	C20—H20	0.9300
C6—C7	1.398 (6)	C21—H21	0.9300
C6—C11	1.513 (7)	C22—C23	1.529 (5)
C7—C8	1.364 (7)	C22—H22A	0.9700
C7—H7	0.9300	C22—H22B	0.9700
C8—C9	1.389 (7)	C23—C24	1.520 (5)
C8—H8	0.9300	C23—H23A	0.9700
C9—C10	1.399 (6)	C23—H23B	0.9700
C9—C12	1.501 (7)	C24—O2	1.429 (4)
C10—H10	0.9300	C24—C25	1.508 (6)
C11—H11A	0.9600	C24—H24	0.9800
C11—H11B	0.9600	C25—C26	1.527 (5)
C11—H11C	0.9600	C25—H25A	0.9700
C12—H12A	0.9600	C25—H25B	0.9700
C12—H12B	0.9600	C26—H26A	0.9700
C12—H12C	0.9600	C26—H26B	0.9700
C13—O4	1.192 (4)	C27—O2	1.410 (5)
C13—O3	1.381 (5)	C27—H27A	0.9600
C13—C14	1.461 (5)	C27—H27B	0.9600
C14—C15	1.324 (5)	C27—H27C	0.9600
C14—H14	0.9300	N1—H1	0.8600
O1—C1—N1	126.2 (4)	C18—C17—C16	122.0 (3)
O1—C1—C2	126.7 (4)	C18—C17—Br1	116.8 (3)
N1—C1—C2	107.2 (3)	C16—C17—Br1	121.1 (3)
C3—C2—C5	128.4 (3)	C19—C18—C17	117.8 (3)
C3—C2—C1	106.0 (3)	C19—C18—H18	121.1
C5—C2—C1	125.6 (3)	C17—C18—H18	121.1
C2—C3—O3	126.1 (3)	F1—C19—C20	118.0 (4)
C2—C3—C4	114.4 (3)	F1—C19—C18	118.5 (4)
O3—C3—C4	119.5 (3)	C20—C19—C18	123.5 (3)
N1—C4—C3	99.0 (3)	C19—C20—C21	117.6 (4)
N1—C4—C26	111.7 (3)	C19—C20—H20	121.2
C3—C4—C26	112.8 (3)	C21—C20—H20	121.2
N1—C4—C22	112.4 (3)	C20—C21—C16	122.2 (4)
C3—C4—C22	111.8 (3)	C20—C21—H21	118.9
C26—C4—C22	108.9 (3)	C16—C21—H21	118.9
C10—C5—C6	120.2 (4)	C23—C22—C4	112.2 (3)
C10—C5—C2	117.0 (4)	C23—C22—H22A	109.2
C6—C5—C2	122.7 (4)	C4—C22—H22A	109.2
C7—C6—C5	117.0 (4)	C23—C22—H22B	109.2
C7—C6—C11	119.8 (4)	C4—C22—H22B	109.2
C5—C6—C11	123.2 (4)	H22A—C22—H22B	107.9
C8—C7—C6	122.3 (5)	C24—C23—C22	110.8 (3)
C8—C7—H7	118.8	C24—C23—H23A	109.5
C6—C7—H7	118.8	C22—C23—H23A	109.5
C7—C8—C9	121.4 (4)	C24—C23—H23B	109.5
C7—C8—H8	119.3	C22—C23—H23B	109.5
C9—C8—H8	119.3	H23A—C23—H23B	108.1
C8—C9—C10	116.9 (4)	O2—C24—C25	106.3 (3)
C8—C9—C12	122.4 (4)	O2—C24—C23	112.4 (3)
C10—C9—C12	120.7 (4)	C25—C24—C23	110.9 (3)
C5—C10—C9	122.2 (4)	O2—C24—H24	109.0
C5—C10—H10	118.9	C25—C24—H24	109.0
C9—C10—H10	118.9	C23—C24—H24	109.0
C6—C11—H11A	109.5	C24—C25—C26	112.1 (3)
C6—C11—H11B	109.5	C24—C25—H25A	109.2
H11A—C11—H11B	109.5	C26—C25—H25A	109.2
C6—C11—H11C	109.5	C24—C25—H25B	109.2
H11A—C11—H11C	109.5	C26—C25—H25B	109.2
H11B—C11—H11C	109.5	H25A—C25—H25B	107.9
C9—C12—H12A	109.5	C25—C26—C4	111.7 (3)
C9—C12—H12B	109.5	C25—C26—H26A	109.3
H12A—C12—H12B	109.5	C4—C26—H26A	109.3
C9—C12—H12C	109.5	C25—C26—H26B	109.3
H12A—C12—H12C	109.5	C4—C26—H26B	109.3
H12B—C12—H12C	109.5	H26A—C26—H26B	107.9
O4—C13—O3	122.2 (3)	O2—C27—H27A	109.5
O4—C13—C14	125.7 (4)	O2—C27—H27B	109.5
O3—C13—C14	112.1 (3)	H27A—C27—H27B	109.5
C15—C14—C13	123.8 (3)	O2—C27—H27C	109.5
C15—C14—H14	118.1	H27A—C27—H27C	109.5
C13—C14—H14	118.1	H27B—C27—H27C	109.5
C14—C15—C16	127.1 (3)	C1—N1—C4	113.4 (3)
C14—C15—H15	116.4	C1—N1—H1	123.3
C16—C15—H15	116.4	C4—N1—H1	123.3
C21—C16—C17	116.8 (3)	C27—O2—C24	115.2 (3)
C21—C16—C15	121.4 (3)	C13—O3—C3	116.7 (3)
C17—C16—C15	121.8 (3)
O1—C1—C2—C3	−178.7 (4)	C21—C16—C17—C18	0.9 (5)
N1—C1—C2—C3	0.4 (5)	C15—C16—C17—C18	−179.8 (3)
O1—C1—C2—C5	0.7 (7)	C21—C16—C17—Br1	−180.0 (3)
N1—C1—C2—C5	179.8 (4)	C15—C16—C17—Br1	−0.7 (5)
C5—C2—C3—O3	−2.3 (7)	C16—C17—C18—C19	−0.8 (6)
C1—C2—C3—O3	177.1 (4)	Br1—C17—C18—C19	−180.0 (3)
C5—C2—C3—C4	179.9 (4)	C17—C18—C19—F1	179.4 (3)
C1—C2—C3—C4	−0.8 (5)	C17—C18—C19—C20	−0.1 (6)
C2—C3—C4—N1	0.8 (4)	F1—C19—C20—C21	−178.6 (3)
O3—C3—C4—N1	−177.2 (3)	C18—C19—C20—C21	0.9 (6)
C2—C3—C4—C26	119.1 (4)	C19—C20—C21—C16	−0.8 (6)
O3—C3—C4—C26	−58.9 (4)	C17—C16—C21—C20	−0.1 (6)
C2—C3—C4—C22	−117.7 (4)	C15—C16—C21—C20	−179.4 (4)
O3—C3—C4—C22	64.2 (4)	N1—C4—C22—C23	68.2 (4)
C3—C2—C5—C10	51.7 (6)	C3—C4—C22—C23	178.5 (3)
C1—C2—C5—C10	−127.5 (4)	C26—C4—C22—C23	−56.1 (4)
C3—C2—C5—C6	−125.6 (5)	C4—C22—C23—C24	56.8 (4)
C1—C2—C5—C6	55.2 (6)	C22—C23—C24—O2	−174.0 (3)
C10—C5—C6—C7	1.2 (6)	C22—C23—C24—C25	−55.1 (4)
C2—C5—C6—C7	178.4 (4)	O2—C24—C25—C26	177.6 (3)
C10—C5—C6—C11	−177.6 (4)	C23—C24—C25—C26	55.1 (4)
C2—C5—C6—C11	−0.4 (7)	C24—C25—C26—C4	−55.9 (5)
C5—C6—C7—C8	−1.0 (7)	N1—C4—C26—C25	−69.6 (4)
C11—C6—C7—C8	177.9 (5)	C3—C4—C26—C25	179.9 (3)
C6—C7—C8—C9	−0.4 (8)	C22—C4—C26—C25	55.1 (4)
C7—C8—C9—C10	1.5 (7)	O1—C1—N1—C4	179.2 (4)
C7—C8—C9—C12	−175.7 (5)	C2—C1—N1—C4	0.1 (5)
C6—C5—C10—C9	−0.1 (6)	C3—C4—N1—C1	−0.5 (4)
C2—C5—C10—C9	−177.4 (4)	C26—C4—N1—C1	−119.6 (4)
C8—C9—C10—C5	−1.3 (6)	C22—C4—N1—C1	117.6 (4)
C12—C9—C10—C5	176.0 (4)	C25—C24—O2—C27	165.5 (4)
O4—C13—C14—C15	−158.5 (4)	C23—C24—O2—C27	−73.0 (5)
O3—C13—C14—C15	19.6 (5)	O4—C13—O3—C3	23.9 (5)
C13—C14—C15—C16	171.6 (3)	C14—C13—O3—C3	−154.3 (3)
C14—C15—C16—C21	−1.4 (6)	C2—C3—O3—C13	64.2 (5)
C14—C15—C16—C17	179.3 (4)	C4—C3—O3—C13	−118.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.11	2.859 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.11	2.859 (4)	145

Symmetry code: (i) .