1-[2,4,6-Trimethyl-3,5-bis-(4-oxopiperidin-1-ylmeth-yl)benz-yl]piperidin-4-one.

In the structure of the title compound, C(27)H(39)N(3)O(3), each of the (4-oxopiperidin-1-yl)methyl residues adopts a flattened chair conformation (with the N and carbonyl groups being oriented to either side of the central C(4) plane) and they occupy positions approximately orthogonal to the central benzene ring [C(benzene)-C-C(methyl-ene)-N torsion angles 103.4 (2), -104.4 (3) and 71.9 (3)°]; further, two of these residues are oriented to one side of the central benzene ring with the third to the other side. In the crystal packing, supra-molecular layers in the ab plane are sustained by C-H⋯O inter-actions.

Related literature

For background to the biological significance of piperidin-4-one and analogous pyran and thio­pyran species, see: El-Subbagh et al. (2000 ▶); Ganellin et al. (1965 ▶); Hagenbach & Gysin (1952 ▶); Ileana et al. (1985 ▶); Mokio et al. (1989 ▶); Pathak et al. (2007 ▶). For a related structure, see: Vijayakumar et al. (2010 ▶).

Experimental

Crystal data

C27H39N3O3

M = 453.61

Triclinic,

a = 7.9315 (16) Å

b = 12.449 (3) Å

c = 14.618 (3) Å

α = 67.641 (3)°

β = 87.749 (4)°

γ = 73.630 (3)°

V = 1277.0 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.28 × 0.21 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.981, T max = 0.987

12284 measured reflections

4490 independent reflections

3008 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.183

S = 1.02

4490 reflections

301 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016570/hg2682sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016570/hg2682Isup2.hkl

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

C27H39N3O3	Z = 2
Mr = 453.61	F(000) = 492
Triclinic, P1	Dx = 1.180 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9315 (16) Å	Cell parameters from 969 reflections
b = 12.449 (3) Å	θ = 2.9–21.9°
c = 14.618 (3) Å	µ = 0.08 mm−1
α = 67.641 (3)°	T = 293 K
β = 87.749 (4)°	Block, colourless
γ = 73.630 (3)°	0.28 × 0.21 × 0.17 mm
V = 1277.0 (5) Å3

Bruker SMART APEX CCD diffractometer	4490 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −9→9
Tmin = 0.981, Tmax = 0.987	k = −14→14
12284 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0929P)2 + 0.3308P] where P = (Fo2 + 2Fc2)/3
4490 reflections	(Δ/σ)max = 0.007
301 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	−0.1090 (3)	−0.3541 (2)	0.4155 (2)	0.1134 (9)
O2	−0.5097 (3)	0.4895 (2)	0.2615 (2)	0.1089 (8)
O3	1.1430 (3)	0.1907 (3)	−0.0499 (2)	0.1334 (11)
N1	0.2978 (2)	−0.20717 (17)	0.36948 (14)	0.0539 (5)
N2	0.0198 (2)	0.35113 (19)	0.26602 (16)	0.0603 (6)
N3	0.6691 (2)	0.18892 (18)	0.05220 (14)	0.0558 (5)
C1	0.4104 (3)	−0.0297 (2)	0.33087 (17)	0.0502 (6)
C2	0.3290 (3)	0.0681 (2)	0.35901 (17)	0.0511 (6)
C3	0.3003 (3)	0.1875 (2)	0.29004 (19)	0.0532 (6)
C4	0.3618 (3)	0.2095 (2)	0.19514 (18)	0.0545 (6)
C5	0.4516 (3)	0.1122 (2)	0.16894 (17)	0.0520 (6)
C6	0.4721 (3)	−0.0076 (2)	0.23580 (18)	0.0511 (6)
C7	0.4264 (3)	−0.1596 (2)	0.39930 (19)	0.0592 (7)
H7A	0.5444	−0.2101	0.3991	0.071*
H7B	0.4088	−0.1636	0.4664	0.071*
C8	0.3258 (3)	−0.3350 (2)	0.4315 (2)	0.0705 (8)
H8A	0.3095	−0.3439	0.4999	0.085*
H8B	0.4462	−0.3799	0.4284	0.085*
C9	0.1999 (4)	−0.3884 (3)	0.3990 (3)	0.0792 (9)
H9A	0.2340	−0.3963	0.3369	0.095*
H9B	0.2100	−0.4689	0.4483	0.095*
C10	0.0127 (4)	−0.3128 (3)	0.3857 (2)	0.0704 (8)
C11	−0.0149 (3)	−0.1805 (2)	0.3333 (2)	0.0684 (7)
H11A	−0.1333	−0.1373	0.3415	0.082*
H11B	−0.0036	−0.1616	0.2630	0.082*
C12	0.1175 (3)	−0.1385 (2)	0.37301 (19)	0.0580 (6)
H12A	0.1019	−0.0531	0.3340	0.070*
H12B	0.0960	−0.1479	0.4410	0.070*
C13	0.2677 (3)	0.0440 (3)	0.46323 (19)	0.0677 (7)
H13A	0.1498	0.0375	0.4643	0.102*
H13B	0.2698	0.1097	0.4819	0.102*
H13C	0.3448	−0.0303	0.5091	0.102*
C14	0.2003 (3)	0.2953 (2)	0.3141 (2)	0.0655 (7)
H14A	0.1946	0.2693	0.3854	0.079*
H14B	0.2641	0.3556	0.2929	0.079*
C15	−0.0916 (3)	0.2725 (2)	0.3062 (2)	0.0587 (6)
H15A	−0.1012	0.2573	0.3761	0.070*
H15B	−0.0373	0.1953	0.3004	0.070*
C16	−0.2748 (3)	0.3271 (3)	0.2531 (2)	0.0770 (8)
H16A	−0.2675	0.3275	0.1866	0.092*
H16B	−0.3491	0.2767	0.2881	0.092*
C17	−0.3573 (4)	0.4534 (3)	0.2471 (2)	0.0750 (8)
C18	−0.2391 (4)	0.5317 (3)	0.2223 (3)	0.1045 (12)
H18A	−0.2927	0.6024	0.2380	0.125*
H18B	−0.2249	0.5597	0.1516	0.125*
C19	−0.0583 (4)	0.4656 (3)	0.2789 (3)	0.0860 (10)
H19A	0.0189	0.5170	0.2551	0.103*
H19B	−0.0698	0.4493	0.3488	0.103*
C20	0.3263 (3)	0.3379 (3)	0.1196 (2)	0.0757 (8)
H20A	0.4242	0.3442	0.0792	0.114*
H20B	0.3107	0.3926	0.1532	0.114*
H20C	0.2214	0.3586	0.0784	0.114*
C21	0.5171 (3)	0.1390 (3)	0.06593 (18)	0.0628 (7)
H21A	0.5507	0.0648	0.0536	0.075*
H21B	0.4215	0.1966	0.0174	0.075*
C22	0.6971 (4)	0.2351 (3)	−0.0532 (2)	0.0842 (10)
H22A	0.5887	0.2925	−0.0905	0.101*
H22B	0.7295	0.1686	−0.0758	0.101*
C23	0.8419 (4)	0.2969 (4)	−0.0716 (3)	0.1011 (12)
H23A	0.8620	0.3253	−0.1416	0.121*
H23B	0.8064	0.3665	−0.0530	0.121*
C24	1.0056 (4)	0.2109 (3)	−0.0130 (2)	0.0797 (9)
C25	0.9854 (3)	0.1473 (3)	0.0935 (2)	0.0755 (8)
H25A	0.9698	0.2031	0.1269	0.091*
H25B	1.0913	0.0811	0.1235	0.091*
C26	0.8270 (3)	0.0975 (2)	0.1068 (2)	0.0644 (7)
H26A	0.8527	0.0309	0.0845	0.077*
H26B	0.8071	0.0659	0.1767	0.077*
C27	0.5526 (3)	−0.1134 (3)	0.2056 (2)	0.0691 (8)
H27A	0.4736	−0.1128	0.1572	0.104*
H27B	0.5726	−0.1879	0.2628	0.104*
H27C	0.6625	−0.1067	0.1777	0.104*

	U11	U22	U33	U12	U13	U23
O1	0.0747 (14)	0.0842 (16)	0.159 (2)	−0.0394 (13)	0.0274 (15)	−0.0133 (15)
O2	0.0508 (12)	0.1078 (18)	0.160 (2)	−0.0044 (12)	0.0228 (13)	−0.0575 (16)
O3	0.0656 (14)	0.245 (3)	0.131 (2)	−0.0694 (18)	0.0524 (14)	−0.105 (2)
N1	0.0428 (10)	0.0519 (12)	0.0582 (12)	−0.0119 (9)	0.0099 (9)	−0.0137 (10)
N2	0.0401 (10)	0.0613 (13)	0.0751 (14)	−0.0127 (9)	0.0124 (9)	−0.0238 (11)
N3	0.0351 (10)	0.0699 (13)	0.0532 (12)	−0.0180 (9)	0.0068 (8)	−0.0122 (10)
C1	0.0308 (11)	0.0641 (15)	0.0553 (14)	−0.0161 (10)	0.0028 (10)	−0.0210 (12)
C2	0.0303 (11)	0.0717 (17)	0.0548 (14)	−0.0155 (11)	0.0042 (10)	−0.0276 (13)
C3	0.0307 (11)	0.0663 (16)	0.0676 (16)	−0.0172 (11)	0.0049 (10)	−0.0288 (13)
C4	0.0301 (11)	0.0641 (16)	0.0664 (16)	−0.0170 (11)	0.0025 (10)	−0.0193 (13)
C5	0.0289 (11)	0.0755 (17)	0.0561 (14)	−0.0225 (11)	0.0062 (10)	−0.0251 (13)
C6	0.0305 (11)	0.0688 (16)	0.0632 (15)	−0.0209 (11)	0.0105 (10)	−0.0312 (13)
C7	0.0401 (12)	0.0672 (17)	0.0615 (15)	−0.0099 (11)	0.0024 (11)	−0.0191 (13)
C8	0.0538 (15)	0.0587 (17)	0.0804 (19)	−0.0076 (13)	0.0117 (13)	−0.0137 (14)
C9	0.078 (2)	0.0552 (17)	0.100 (2)	−0.0240 (15)	0.0208 (17)	−0.0225 (16)
C10	0.0621 (17)	0.0688 (18)	0.0790 (19)	−0.0278 (14)	0.0131 (14)	−0.0213 (15)
C11	0.0518 (15)	0.0663 (17)	0.0783 (18)	−0.0207 (13)	0.0024 (13)	−0.0157 (14)
C12	0.0443 (13)	0.0559 (15)	0.0659 (16)	−0.0132 (11)	0.0056 (11)	−0.0161 (12)
C13	0.0547 (15)	0.0854 (19)	0.0636 (17)	−0.0163 (14)	0.0091 (12)	−0.0327 (15)
C14	0.0443 (14)	0.0750 (18)	0.0871 (19)	−0.0201 (13)	0.0092 (13)	−0.0403 (15)
C15	0.0414 (13)	0.0625 (16)	0.0712 (16)	−0.0131 (11)	0.0062 (11)	−0.0262 (13)
C16	0.0466 (15)	0.087 (2)	0.098 (2)	−0.0117 (14)	0.0010 (14)	−0.0419 (18)
C17	0.0468 (15)	0.080 (2)	0.085 (2)	−0.0035 (14)	0.0067 (13)	−0.0281 (16)
C18	0.0654 (19)	0.064 (2)	0.153 (3)	−0.0025 (16)	0.018 (2)	−0.022 (2)
C19	0.0603 (17)	0.0647 (19)	0.136 (3)	−0.0224 (15)	0.0241 (18)	−0.0402 (19)
C20	0.0501 (15)	0.0744 (19)	0.086 (2)	−0.0166 (13)	0.0093 (14)	−0.0149 (16)
C21	0.0425 (13)	0.0917 (19)	0.0569 (15)	−0.0282 (13)	0.0075 (11)	−0.0257 (14)
C22	0.0580 (16)	0.116 (3)	0.0561 (17)	−0.0340 (17)	0.0056 (13)	−0.0031 (16)
C23	0.079 (2)	0.122 (3)	0.086 (2)	−0.052 (2)	0.0246 (18)	−0.008 (2)
C24	0.0575 (17)	0.123 (3)	0.092 (2)	−0.0536 (18)	0.0352 (16)	−0.060 (2)
C25	0.0408 (14)	0.105 (2)	0.084 (2)	−0.0235 (14)	0.0092 (13)	−0.0388 (18)
C26	0.0408 (13)	0.0757 (18)	0.0666 (16)	−0.0169 (12)	0.0054 (11)	−0.0166 (14)
C27	0.0569 (15)	0.0853 (19)	0.0825 (19)	−0.0324 (14)	0.0234 (14)	−0.0440 (16)

O1—C10	1.209 (3)	C13—H13A	0.9600
O2—C17	1.205 (3)	C13—H13B	0.9600
O3—C24	1.202 (3)	C13—H13C	0.9600
N1—C12	1.455 (3)	C14—H14A	0.9700
N1—C8	1.457 (3)	C14—H14B	0.9700
N1—C7	1.468 (3)	C15—C16	1.518 (3)
N2—C15	1.447 (3)	C15—H15A	0.9700
N2—C19	1.465 (3)	C15—H15B	0.9700
N2—C14	1.474 (3)	C16—C17	1.493 (4)
N3—C26	1.444 (3)	C16—H16A	0.9700
N3—C22	1.457 (3)	C16—H16B	0.9700
N3—C21	1.480 (3)	C17—C18	1.477 (4)
C1—C6	1.407 (3)	C18—C19	1.526 (4)
C1—C2	1.409 (3)	C18—H18A	0.9700
C1—C7	1.515 (3)	C18—H18B	0.9700
C2—C3	1.402 (3)	C19—H19A	0.9700
C2—C13	1.524 (3)	C19—H19B	0.9700
C3—C4	1.404 (3)	C20—H20A	0.9600
C3—C14	1.513 (3)	C20—H20B	0.9600
C4—C5	1.402 (3)	C20—H20C	0.9600
C4—C20	1.511 (4)	C21—H21A	0.9700
C5—C6	1.405 (3)	C21—H21B	0.9700
C5—C21	1.517 (3)	C22—C23	1.516 (4)
C6—C27	1.511 (3)	C22—H22A	0.9700
C7—H7A	0.9700	C22—H22B	0.9700
C7—H7B	0.9700	C23—C24	1.474 (5)
C8—C9	1.522 (4)	C23—H23A	0.9700
C8—H8A	0.9700	C23—H23B	0.9700
C8—H8B	0.9700	C24—C25	1.480 (4)
C9—C10	1.491 (4)	C25—C26	1.525 (3)
C9—H9A	0.9700	C25—H25A	0.9700
C9—H9B	0.9700	C25—H25B	0.9700
C10—C11	1.482 (4)	C26—H26A	0.9700
C11—C12	1.517 (3)	C26—H26B	0.9700
C11—H11A	0.9700	C27—H27A	0.9600
C11—H11B	0.9700	C27—H27B	0.9600
C12—H12A	0.9700	C27—H27C	0.9600
C12—H12B	0.9700
C12—N1—C8	109.97 (18)	N2—C15—C16	112.2 (2)
C12—N1—C7	111.77 (19)	N2—C15—H15A	109.2
C8—N1—C7	110.82 (19)	C16—C15—H15A	109.2
C15—N2—C19	109.09 (19)	N2—C15—H15B	109.2
C15—N2—C14	112.1 (2)	C16—C15—H15B	109.2
C19—N2—C14	109.6 (2)	H15A—C15—H15B	107.9
C26—N3—C22	109.5 (2)	C17—C16—C15	112.2 (2)
C26—N3—C21	111.39 (19)	C17—C16—H16A	109.2
C22—N3—C21	108.5 (2)	C15—C16—H16A	109.2
C6—C1—C2	120.0 (2)	C17—C16—H16B	109.2
C6—C1—C7	118.4 (2)	C15—C16—H16B	109.2
C2—C1—C7	121.5 (2)	H16A—C16—H16B	107.9
C3—C2—C1	119.8 (2)	O2—C17—C18	122.0 (3)
C3—C2—C13	120.1 (2)	O2—C17—C16	122.6 (3)
C1—C2—C13	120.0 (2)	C18—C17—C16	115.4 (2)
C2—C3—C4	120.0 (2)	C17—C18—C19	112.1 (3)
C2—C3—C14	121.7 (2)	C17—C18—H18A	109.2
C4—C3—C14	118.3 (2)	C19—C18—H18A	109.2
C5—C4—C3	120.2 (2)	C17—C18—H18B	109.2
C5—C4—C20	119.6 (2)	C19—C18—H18B	109.2
C3—C4—C20	120.2 (2)	H18A—C18—H18B	107.9
C4—C5—C6	120.0 (2)	N2—C19—C18	111.2 (3)
C4—C5—C21	118.9 (2)	N2—C19—H19A	109.4
C6—C5—C21	121.0 (2)	C18—C19—H19A	109.4
C5—C6—C1	119.8 (2)	N2—C19—H19B	109.4
C5—C6—C27	120.9 (2)	C18—C19—H19B	109.4
C1—C6—C27	119.2 (2)	H19A—C19—H19B	108.0
N1—C7—C1	112.09 (18)	C4—C20—H20A	109.5
N1—C7—H7A	109.2	C4—C20—H20B	109.5
C1—C7—H7A	109.2	H20A—C20—H20B	109.5
N1—C7—H7B	109.2	C4—C20—H20C	109.5
C1—C7—H7B	109.2	H20A—C20—H20C	109.5
H7A—C7—H7B	107.9	H20B—C20—H20C	109.5
N1—C8—C9	112.0 (2)	N3—C21—C5	113.1 (2)
N1—C8—H8A	109.2	N3—C21—H21A	108.9
C9—C8—H8A	109.2	C5—C21—H21A	108.9
N1—C8—H8B	109.2	N3—C21—H21B	108.9
C9—C8—H8B	109.2	C5—C21—H21B	108.9
H8A—C8—H8B	107.9	H21A—C21—H21B	107.8
C10—C9—C8	112.8 (2)	N3—C22—C23	110.2 (3)
C10—C9—H9A	109.0	N3—C22—H22A	109.6
C8—C9—H9A	109.0	C23—C22—H22A	109.6
C10—C9—H9B	109.0	N3—C22—H22B	109.6
C8—C9—H9B	109.0	C23—C22—H22B	109.6
H9A—C9—H9B	107.8	H22A—C22—H22B	108.1
O1—C10—C11	121.5 (3)	C24—C23—C22	109.8 (3)
O1—C10—C9	123.7 (3)	C24—C23—H23A	109.7
C11—C10—C9	114.8 (2)	C22—C23—H23A	109.7
C10—C11—C12	111.3 (2)	C24—C23—H23B	109.7
C10—C11—H11A	109.4	C22—C23—H23B	109.7
C12—C11—H11A	109.4	H23A—C23—H23B	108.2
C10—C11—H11B	109.4	O3—C24—C23	122.3 (3)
C12—C11—H11B	109.4	O3—C24—C25	122.9 (3)
H11A—C11—H11B	108.0	C23—C24—C25	114.8 (2)
N1—C12—C11	111.6 (2)	C24—C25—C26	110.8 (2)
N1—C12—H12A	109.3	C24—C25—H25A	109.5
C11—C12—H12A	109.3	C26—C25—H25A	109.5
N1—C12—H12B	109.3	C24—C25—H25B	109.5
C11—C12—H12B	109.3	C26—C25—H25B	109.5
H12A—C12—H12B	108.0	H25A—C25—H25B	108.1
C2—C13—H13A	109.5	N3—C26—C25	112.1 (2)
C2—C13—H13B	109.5	N3—C26—H26A	109.2
H13A—C13—H13B	109.5	C25—C26—H26A	109.2
C2—C13—H13C	109.5	N3—C26—H26B	109.2
H13A—C13—H13C	109.5	C25—C26—H26B	109.2
H13B—C13—H13C	109.5	H26A—C26—H26B	107.9
N2—C14—C3	112.7 (2)	C6—C27—H27A	109.5
N2—C14—H14A	109.1	C6—C27—H27B	109.5
C3—C14—H14A	109.1	H27A—C27—H27B	109.5
N2—C14—H14B	109.1	C6—C27—H27C	109.5
C3—C14—H14B	109.1	H27A—C27—H27C	109.5
H14A—C14—H14B	107.8	H27B—C27—H27C	109.5
C6—C1—C2—C3	3.8 (3)	O1—C10—C11—C12	133.7 (3)
C7—C1—C2—C3	−173.44 (19)	C9—C10—C11—C12	−45.6 (4)
C6—C1—C2—C13	−177.93 (19)	C8—N1—C12—C11	−61.6 (3)
C7—C1—C2—C13	4.8 (3)	C7—N1—C12—C11	174.8 (2)
C1—C2—C3—C4	−3.7 (3)	C10—C11—C12—N1	54.7 (3)
C13—C2—C3—C4	178.0 (2)	C15—N2—C14—C3	68.0 (3)
C1—C2—C3—C14	174.9 (2)	C19—N2—C14—C3	−170.7 (2)
C13—C2—C3—C14	−3.3 (3)	C2—C3—C14—N2	−104.4 (3)
C2—C3—C4—C5	0.1 (3)	C4—C3—C14—N2	74.3 (3)
C14—C3—C4—C5	−178.57 (19)	C19—N2—C15—C16	61.4 (3)
C2—C3—C4—C20	178.1 (2)	C14—N2—C15—C16	−177.0 (2)
C14—C3—C4—C20	−0.6 (3)	N2—C15—C16—C17	−51.2 (3)
C3—C4—C5—C6	3.4 (3)	C15—C16—C17—O2	−137.8 (3)
C20—C4—C5—C6	−174.6 (2)	C15—C16—C17—C18	42.1 (4)
C3—C4—C5—C21	−179.76 (19)	O2—C17—C18—C19	136.7 (3)
C20—C4—C5—C21	2.2 (3)	C16—C17—C18—C19	−43.1 (4)
C4—C5—C6—C1	−3.3 (3)	C15—N2—C19—C18	−61.9 (3)
C21—C5—C6—C1	179.92 (19)	C14—N2—C19—C18	175.0 (2)
C4—C5—C6—C27	174.0 (2)	C17—C18—C19—N2	52.8 (4)
C21—C5—C6—C27	−2.8 (3)	C26—N3—C21—C5	71.4 (3)
C2—C1—C6—C5	−0.3 (3)	C22—N3—C21—C5	−168.0 (2)
C7—C1—C6—C5	177.04 (19)	C4—C5—C21—N3	71.9 (3)
C2—C1—C6—C27	−177.6 (2)	C6—C5—C21—N3	−111.3 (2)
C7—C1—C6—C27	−0.3 (3)	C26—N3—C22—C23	−63.1 (3)
C12—N1—C7—C1	−61.7 (3)	C21—N3—C22—C23	175.1 (3)
C8—N1—C7—C1	175.3 (2)	N3—C22—C23—C24	57.7 (4)
C6—C1—C7—N1	−73.9 (2)	C22—C23—C24—O3	126.4 (3)
C2—C1—C7—N1	103.4 (2)	C22—C23—C24—C25	−50.7 (4)
C12—N1—C8—C9	58.7 (3)	O3—C24—C25—C26	−129.9 (3)
C7—N1—C8—C9	−177.2 (2)	C23—C24—C25—C26	47.2 (4)
N1—C8—C9—C10	−49.5 (3)	C22—N3—C26—C25	60.0 (3)
C8—C9—C10—O1	−135.9 (3)	C21—N3—C26—C25	180.0 (2)
C8—C9—C10—C11	43.5 (4)	C24—C25—C26—N3	−51.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20a···N3	0.96	2.46	3.184 (4)	132
C9—H9a···O2i	0.97	2.60	3.412 (5)	142
C21—H21b···O3ii	0.97	2.48	3.252 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20a⋯N3	0.96	2.46	3.184 (4)	132
C9—H9a⋯O2i	0.97	2.60	3.412 (5)	142
C21—H21b⋯O3ii	0.97	2.48	3.252 (4)	136

Symmetry codes: (i) ; (ii) .