Ethyl 4-[2-(3,5-dimethyl-4-oxo-2,6-diphenyl-piperidin-1-yl)-2-oxoeth-yl]piperazine-1-carboxyl-ate.

In the title compound, C(28)H(35)N(3)O(4), the piperidine ring adopts a boat conformation while the piperazine ring adopts a chair conformation with an equatorial orientation of the phenyl groups. The dihedral angle between the mean planes of the benzene rings is 74.14 (8)°. The mol-ecular conformation is stabilized by a weak intra-molecular C-H⋯N inter-action and the crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For the biological activity of related structures, see: El-subbagh et al. (2000 ▶); Emami et al. (2006 ▶); Foroumadi et al. (2007 ▶); Katritzky & Fan (1990 ▶); Mobio et al. (1989 ▶). For geometrical analysis, see: Cremer & Pople (1975 ▶); Emami et al. (2006 ▶); Foroumadi et al. (2007 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C28H35N3O4

M = 477.59

Monoclinic,

a = 10.9073 (3) Å

b = 19.1940 (6) Å

c = 12.2246 (3) Å

β = 91.809 (2)°

V = 2558.00 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.975, T max = 0.984

31692 measured reflections

6941 independent reflections

4703 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.142

S = 1.01

6941 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003412/zq2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003412/zq2086Isup2.hkl

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

C28H35N3O4	Z = 4
Mr = 477.59	F(000) = 1024
Monoclinic, P21/n	Dx = 1.240 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.9073 (3) Å	θ = 2.0–29.2°
b = 19.1940 (6) Å	µ = 0.08 mm−1
c = 12.2246 (3) Å	T = 293 K
β = 91.809 (2)°	Prism, colourless
V = 2558.00 (12) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	6941 independent reflections
Radiation source: fine-focus sealed tube	4703 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 29.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −14→14
Tmin = 0.975, Tmax = 0.984	k = −26→26
31692 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.4844P] where P = (Fo2 + 2Fc2)/3
6941 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.18 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
O2	0.30276 (10)	0.02315 (6)	0.45786 (8)	0.0474 (3)
N1	0.27565 (10)	0.01252 (6)	0.27464 (8)	0.0346 (2)
O3	0.83211 (11)	0.26851 (6)	0.33044 (11)	0.0674 (4)
O4	0.87576 (10)	0.17829 (6)	0.44239 (10)	0.0594 (3)
N2	0.48203 (10)	0.12188 (6)	0.31107 (9)	0.0354 (2)
N3	0.72912 (11)	0.16692 (7)	0.31251 (11)	0.0469 (3)
O1	0.36909 (18)	−0.11603 (8)	0.02744 (11)	0.1013 (6)
C21	0.35944 (12)	0.12158 (7)	0.35490 (11)	0.0385 (3)
H21A	0.3047	0.1482	0.3068	0.046*
H21B	0.3618	0.1441	0.4260	0.046*
C20	0.30991 (11)	0.04850 (7)	0.36633 (10)	0.0346 (3)
C1	0.24946 (13)	−0.06249 (7)	0.28730 (11)	0.0379 (3)
H1	0.2739	−0.0741	0.3630	0.045*
C23	0.69961 (13)	0.09713 (8)	0.34954 (14)	0.0481 (4)
H23A	0.7577	0.0831	0.4071	0.058*
H23B	0.7059	0.0646	0.2893	0.058*
C6	0.11293 (13)	−0.07761 (7)	0.27691 (11)	0.0391 (3)
C2	0.33470 (14)	−0.10402 (8)	0.21546 (12)	0.0458 (3)
H2	0.3107	−0.1532	0.2182	0.055*
C7	0.03802 (14)	−0.04948 (8)	0.35541 (12)	0.0454 (3)
H7	0.0729	−0.0228	0.4118	0.054*
C12	0.18481 (14)	0.09997 (7)	0.14324 (11)	0.0414 (3)
C5	0.28059 (13)	0.04335 (7)	0.16348 (10)	0.0380 (3)
H5	0.3615	0.0648	0.1569	0.046*
C4	0.26648 (15)	−0.01210 (8)	0.07262 (11)	0.0473 (3)
H4	0.1785	−0.0218	0.0642	0.057*
C22	0.57133 (12)	0.09542 (7)	0.39208 (12)	0.0405 (3)
H22A	0.5503	0.0479	0.4110	0.049*
H22B	0.5682	0.1234	0.4580	0.049*
C11	0.05813 (15)	−0.11776 (8)	0.19519 (13)	0.0498 (4)
H11	0.1063	−0.1380	0.1424	0.060*
C3	0.32775 (16)	−0.08057 (9)	0.09817 (13)	0.0540 (4)
C13	0.06182 (15)	0.08840 (9)	0.15817 (13)	0.0518 (4)
H13	0.0359	0.0452	0.1832	0.062*
C25	0.51477 (13)	0.19283 (7)	0.28016 (12)	0.0434 (3)
H25A	0.5134	0.2228	0.3440	0.052*
H25B	0.4549	0.2104	0.2266	0.052*
C24	0.64026 (14)	0.19466 (9)	0.23281 (12)	0.0490 (4)
H24A	0.6408	0.1670	0.1664	0.059*
H24B	0.6616	0.2422	0.2145	0.059*
C8	−0.08692 (14)	−0.06037 (9)	0.35137 (14)	0.0516 (4)
H8	−0.1355	−0.0410	0.4046	0.062*
C9	−0.13964 (15)	−0.09967 (9)	0.26901 (15)	0.0560 (4)
H9	−0.2239	−0.1070	0.2660	0.067*
C17	0.21955 (18)	0.16440 (9)	0.10412 (14)	0.0577 (4)
H17	0.3017	0.1731	0.0913	0.069*
C26	0.81377 (13)	0.20954 (8)	0.35904 (13)	0.0470 (3)
C10	−0.06694 (16)	−0.12810 (9)	0.19096 (15)	0.0590 (4)
H10	−0.1025	−0.1546	0.1347	0.071*
C18	0.46803 (16)	−0.09787 (11)	0.25605 (16)	0.0661 (5)
H18A	0.4750	−0.1126	0.3310	0.099*
H18B	0.4943	−0.0503	0.2504	0.099*
H18C	0.5187	−0.1269	0.2122	0.099*
C27	0.97832 (14)	0.21660 (10)	0.49077 (15)	0.0575 (4)
H27A	0.9891	0.2040	0.5673	0.069*
H27B	0.9616	0.2662	0.4867	0.069*
C16	0.1336 (2)	0.21594 (9)	0.08396 (15)	0.0719 (6)
H16	0.1586	0.2593	0.0590	0.086*
C14	−0.02354 (18)	0.14019 (11)	0.13642 (15)	0.0678 (5)
H14	−0.1063	0.1315	0.1465	0.081*
C15	0.0126 (2)	0.20387 (11)	0.10038 (16)	0.0750 (6)
H15	−0.0450	0.2388	0.0871	0.090*
C19	0.3060 (2)	0.01732 (12)	−0.03613 (14)	0.0801 (7)
H19A	0.2654	0.0610	−0.0497	0.120*
H19B	0.2845	−0.0148	−0.0937	0.120*
H19C	0.3932	0.0244	−0.0336	0.120*
C28	1.09184 (17)	0.20086 (12)	0.43263 (18)	0.0743 (5)
H28A	1.1589	0.2266	0.4653	0.111*
H28B	1.0813	0.2138	0.3571	0.111*
H28C	1.1090	0.1519	0.4377	0.111*

	U11	U22	U33	U12	U13	U23
O2	0.0544 (6)	0.0553 (6)	0.0324 (5)	−0.0062 (5)	0.0018 (4)	0.0037 (4)
N1	0.0375 (6)	0.0359 (6)	0.0303 (5)	−0.0015 (4)	0.0027 (4)	0.0030 (4)
O3	0.0553 (7)	0.0542 (7)	0.0916 (9)	−0.0118 (5)	−0.0117 (6)	0.0157 (7)
O4	0.0454 (6)	0.0619 (7)	0.0702 (8)	−0.0039 (5)	−0.0110 (5)	0.0083 (6)
N2	0.0334 (5)	0.0359 (6)	0.0368 (6)	−0.0021 (4)	0.0000 (4)	0.0029 (4)
N3	0.0357 (6)	0.0506 (7)	0.0544 (7)	−0.0048 (5)	0.0009 (5)	0.0106 (6)
O1	0.1630 (17)	0.0893 (10)	0.0528 (8)	0.0586 (11)	0.0210 (9)	−0.0109 (7)
C21	0.0356 (7)	0.0385 (7)	0.0414 (7)	0.0010 (5)	0.0016 (5)	−0.0017 (6)
C20	0.0284 (6)	0.0408 (7)	0.0347 (7)	0.0021 (5)	0.0036 (5)	0.0009 (5)
C1	0.0429 (7)	0.0350 (7)	0.0359 (7)	0.0000 (5)	0.0037 (5)	0.0029 (5)
C23	0.0386 (7)	0.0415 (8)	0.0642 (10)	0.0019 (6)	0.0009 (7)	0.0053 (7)
C6	0.0447 (7)	0.0325 (6)	0.0402 (7)	−0.0026 (5)	0.0020 (6)	0.0034 (5)
C2	0.0509 (8)	0.0414 (7)	0.0454 (8)	0.0084 (6)	0.0059 (6)	0.0003 (6)
C7	0.0473 (8)	0.0467 (8)	0.0423 (8)	−0.0063 (6)	0.0044 (6)	−0.0023 (6)
C12	0.0502 (8)	0.0430 (7)	0.0308 (6)	0.0022 (6)	0.0003 (6)	0.0038 (5)
C5	0.0400 (7)	0.0436 (7)	0.0306 (6)	−0.0016 (6)	0.0037 (5)	0.0061 (5)
C4	0.0538 (9)	0.0560 (9)	0.0323 (7)	0.0098 (7)	0.0023 (6)	−0.0018 (6)
C22	0.0381 (7)	0.0391 (7)	0.0439 (7)	−0.0009 (5)	−0.0020 (6)	0.0079 (6)
C11	0.0549 (9)	0.0421 (8)	0.0525 (9)	−0.0010 (7)	0.0014 (7)	−0.0093 (7)
C3	0.0638 (10)	0.0560 (9)	0.0426 (8)	0.0128 (8)	0.0065 (7)	−0.0071 (7)
C13	0.0530 (9)	0.0537 (9)	0.0491 (9)	0.0088 (7)	0.0108 (7)	0.0091 (7)
C25	0.0416 (7)	0.0406 (7)	0.0475 (8)	−0.0032 (6)	−0.0077 (6)	0.0109 (6)
C24	0.0485 (8)	0.0568 (9)	0.0415 (8)	−0.0098 (7)	−0.0012 (6)	0.0114 (7)
C8	0.0465 (8)	0.0525 (9)	0.0563 (9)	0.0005 (7)	0.0090 (7)	0.0049 (7)
C9	0.0439 (8)	0.0526 (9)	0.0710 (11)	−0.0026 (7)	−0.0050 (8)	0.0072 (8)
C17	0.0710 (11)	0.0515 (9)	0.0501 (9)	−0.0067 (8)	−0.0075 (8)	0.0152 (7)
C26	0.0344 (7)	0.0501 (9)	0.0565 (9)	−0.0004 (6)	0.0049 (6)	0.0050 (7)
C10	0.0600 (10)	0.0494 (9)	0.0665 (11)	−0.0061 (7)	−0.0146 (8)	−0.0075 (8)
C18	0.0532 (10)	0.0853 (13)	0.0599 (10)	0.0208 (9)	0.0053 (8)	−0.0007 (9)
C27	0.0483 (9)	0.0631 (10)	0.0605 (10)	0.0028 (7)	−0.0062 (7)	−0.0116 (8)
C16	0.1107 (17)	0.0461 (10)	0.0582 (11)	0.0082 (10)	−0.0092 (11)	0.0140 (8)
C14	0.0632 (11)	0.0812 (13)	0.0598 (11)	0.0263 (10)	0.0130 (8)	0.0089 (10)
C15	0.0996 (16)	0.0673 (12)	0.0581 (11)	0.0372 (12)	0.0015 (11)	0.0078 (9)
C19	0.1185 (18)	0.0870 (14)	0.0359 (9)	0.0339 (13)	0.0186 (10)	0.0095 (9)
C28	0.0501 (10)	0.0823 (14)	0.0905 (14)	0.0029 (9)	0.0049 (9)	−0.0082 (11)

O2—C20	1.2250 (15)	C4—H4	0.9800
N1—C20	1.3590 (17)	C22—H22A	0.9700
N1—C1	1.4768 (17)	C22—H22B	0.9700
N1—C5	1.4846 (16)	C11—C10	1.378 (2)
O3—C26	1.2032 (19)	C11—H11	0.9300
O4—C26	1.3460 (18)	C13—C14	1.382 (2)
O4—C27	1.4491 (19)	C13—H13	0.9300
N2—C21	1.4561 (17)	C25—C24	1.503 (2)
N2—C22	1.4583 (16)	C25—H25A	0.9700
N2—C25	1.4606 (17)	C25—H25B	0.9700
N3—C26	1.3461 (19)	C24—H24A	0.9700
N3—C23	1.4534 (19)	C24—H24B	0.9700
N3—C24	1.4535 (18)	C8—C9	1.370 (2)
O1—C3	1.1995 (19)	C8—H8	0.9300
C21—C20	1.5111 (19)	C9—C10	1.373 (3)
C21—H21A	0.9700	C9—H9	0.9300
C21—H21B	0.9700	C17—C16	1.380 (3)
C1—C6	1.519 (2)	C17—H17	0.9300
C1—C2	1.5240 (19)	C10—H10	0.9300
C1—H1	0.9800	C18—H18A	0.9600
C23—C22	1.508 (2)	C18—H18B	0.9600
C23—H23A	0.9700	C18—H18C	0.9600
C23—H23B	0.9700	C27—C28	1.478 (2)
C6—C11	1.383 (2)	C27—H27A	0.9700
C6—C7	1.389 (2)	C27—H27B	0.9700
C2—C3	1.502 (2)	C16—C15	1.362 (3)
C2—C18	1.526 (2)	C16—H16	0.9300
C2—H2	0.9800	C14—C15	1.362 (3)
C7—C8	1.378 (2)	C14—H14	0.9300
C7—H7	0.9300	C15—H15	0.9300
C12—C13	1.378 (2)	C19—H19A	0.9600
C12—C17	1.383 (2)	C19—H19B	0.9600
C12—C5	1.5224 (19)	C19—H19C	0.9600
C5—C4	1.542 (2)	C28—H28A	0.9600
C5—H5	0.9800	C28—H28B	0.9600
C4—C3	1.503 (2)	C28—H28C	0.9600
C4—C19	1.519 (2)
C20—N1—C1	117.26 (10)	O1—C3—C2	120.61 (15)
C20—N1—C5	122.37 (11)	O1—C3—C4	121.42 (15)
C1—N1—C5	119.82 (10)	C2—C3—C4	117.97 (13)
C26—O4—C27	116.47 (13)	C12—C13—C14	120.76 (16)
C21—N2—C22	110.50 (10)	C12—C13—H13	119.6
C21—N2—C25	109.50 (10)	C14—C13—H13	119.6
C22—N2—C25	109.69 (10)	N2—C25—C24	110.76 (12)
C26—N3—C23	125.75 (13)	N2—C25—H25A	109.5
C26—N3—C24	119.64 (13)	C24—C25—H25A	109.5
C23—N3—C24	113.39 (12)	N2—C25—H25B	109.5
N2—C21—C20	111.89 (11)	C24—C25—H25B	109.5
N2—C21—H21A	109.2	H25A—C25—H25B	108.1
C20—C21—H21A	109.2	N3—C24—C25	109.23 (12)
N2—C21—H21B	109.2	N3—C24—H24A	109.8
C20—C21—H21B	109.2	C25—C24—H24A	109.8
H21A—C21—H21B	107.9	N3—C24—H24B	109.8
O2—C20—N1	121.85 (12)	C25—C24—H24B	109.8
O2—C20—C21	119.11 (12)	H24A—C24—H24B	108.3
N1—C20—C21	119.03 (11)	C9—C8—C7	120.10 (16)
N1—C1—C6	111.71 (10)	C9—C8—H8	120.0
N1—C1—C2	109.03 (11)	C7—C8—H8	120.0
C6—C1—C2	117.79 (12)	C8—C9—C10	119.43 (16)
N1—C1—H1	105.8	C8—C9—H9	120.3
C6—C1—H1	105.8	C10—C9—H9	120.3
C2—C1—H1	105.8	C16—C17—C12	120.73 (18)
N3—C23—C22	110.14 (12)	C16—C17—H17	119.6
N3—C23—H23A	109.6	C12—C17—H17	119.6
C22—C23—H23A	109.6	O3—C26—O4	123.71 (14)
N3—C23—H23B	109.6	O3—C26—N3	124.54 (14)
C22—C23—H23B	109.6	O4—C26—N3	111.75 (13)
H23A—C23—H23B	108.1	C9—C10—C11	120.64 (15)
C11—C6—C7	117.74 (14)	C9—C10—H10	119.7
C11—C6—C1	124.57 (13)	C11—C10—H10	119.7
C7—C6—C1	117.68 (12)	C2—C18—H18A	109.5
C3—C2—C1	112.33 (12)	C2—C18—H18B	109.5
C3—C2—C18	107.81 (14)	H18A—C18—H18B	109.5
C1—C2—C18	111.38 (13)	C2—C18—H18C	109.5
C3—C2—H2	108.4	H18A—C18—H18C	109.5
C1—C2—H2	108.4	H18B—C18—H18C	109.5
C18—C2—H2	108.4	O4—C27—C28	110.34 (15)
C8—C7—C6	121.26 (14)	O4—C27—H27A	109.6
C8—C7—H7	119.4	C28—C27—H27A	109.6
C6—C7—H7	119.4	O4—C27—H27B	109.6
C13—C12—C17	117.94 (14)	C28—C27—H27B	109.6
C13—C12—C5	121.97 (13)	H27A—C27—H27B	108.1
C17—C12—C5	120.03 (14)	C15—C16—C17	120.54 (18)
N1—C5—C12	112.88 (11)	C15—C16—H16	119.7
N1—C5—C4	112.24 (11)	C17—C16—H16	119.7
C12—C5—C4	108.85 (11)	C15—C14—C13	120.53 (19)
N1—C5—H5	107.5	C15—C14—H14	119.7
C12—C5—H5	107.5	C13—C14—H14	119.7
C4—C5—H5	107.5	C14—C15—C16	119.48 (17)
C3—C4—C19	111.72 (14)	C14—C15—H15	120.3
C3—C4—C5	114.84 (12)	C16—C15—H15	120.3
C19—C4—C5	110.43 (14)	C4—C19—H19A	109.5
C3—C4—H4	106.4	C4—C19—H19B	109.5
C19—C4—H4	106.4	H19A—C19—H19B	109.5
C5—C4—H4	106.4	C4—C19—H19C	109.5
N2—C22—C23	111.42 (12)	H19A—C19—H19C	109.5
N2—C22—H22A	109.3	H19B—C19—H19C	109.5
C23—C22—H22A	109.3	C27—C28—H28A	109.5
N2—C22—H22B	109.3	C27—C28—H28B	109.5
C23—C22—H22B	109.3	H28A—C28—H28B	109.5
H22A—C22—H22B	108.0	C27—C28—H28C	109.5
C10—C11—C6	120.82 (15)	H28A—C28—H28C	109.5
C10—C11—H11	119.6	H28B—C28—H28C	109.5
C6—C11—H11	119.6
C22—N2—C21—C20	−70.96 (14)	C25—N2—C22—C23	−57.61 (15)
C25—N2—C21—C20	168.12 (11)	N3—C23—C22—N2	54.42 (16)
C1—N1—C20—O2	−10.29 (18)	C7—C6—C11—C10	1.3 (2)
C5—N1—C20—O2	178.25 (12)	C1—C6—C11—C10	−179.10 (14)
C1—N1—C20—C21	169.07 (11)	C1—C2—C3—O1	−164.94 (19)
C5—N1—C20—C21	−2.39 (17)	C18—C2—C3—O1	72.0 (2)
N2—C21—C20—O2	107.37 (14)	C1—C2—C3—C4	14.4 (2)
N2—C21—C20—N1	−72.01 (15)	C18—C2—C3—C4	−108.69 (17)
C20—N1—C1—C6	106.90 (13)	C19—C4—C3—O1	−21.7 (3)
C5—N1—C1—C6	−81.41 (14)	C5—C4—C3—O1	−148.50 (19)
C20—N1—C1—C2	−121.17 (12)	C19—C4—C3—C2	158.92 (17)
C5—N1—C1—C2	50.52 (15)	C5—C4—C3—C2	32.2 (2)
C26—N3—C23—C22	113.00 (16)	C17—C12—C13—C14	−1.1 (2)
C24—N3—C23—C22	−54.22 (17)	C5—C12—C13—C14	−178.29 (15)
N1—C1—C6—C11	116.25 (15)	C21—N2—C25—C24	−179.06 (11)
C2—C1—C6—C11	−11.1 (2)	C22—N2—C25—C24	59.52 (15)
N1—C1—C6—C7	−64.17 (16)	C26—N3—C24—C25	−112.15 (15)
C2—C1—C6—C7	168.49 (12)	C23—N3—C24—C25	55.93 (17)
N1—C1—C2—C3	−54.18 (16)	N2—C25—C24—N3	−57.96 (16)
C6—C1—C2—C3	74.44 (17)	C6—C7—C8—C9	0.1 (2)
N1—C1—C2—C18	66.89 (16)	C7—C8—C9—C10	0.1 (2)
C6—C1—C2—C18	−164.50 (13)	C13—C12—C17—C16	1.9 (2)
C11—C6—C7—C8	−0.8 (2)	C5—C12—C17—C16	179.12 (15)
C1—C6—C7—C8	179.55 (13)	C27—O4—C26—O3	−6.8 (2)
C20—N1—C5—C12	−69.90 (15)	C27—O4—C26—N3	173.41 (13)
C1—N1—C5—C12	118.85 (13)	C23—N3—C26—O3	−175.88 (16)
C20—N1—C5—C4	166.64 (12)	C24—N3—C26—O3	−9.4 (2)
C1—N1—C5—C4	−4.61 (16)	C23—N3—C26—O4	3.9 (2)
C13—C12—C5—N1	−54.40 (18)	C24—N3—C26—O4	170.36 (13)
C17—C12—C5—N1	128.50 (14)	C8—C9—C10—C11	0.4 (3)
C13—C12—C5—C4	70.92 (17)	C6—C11—C10—C9	−1.1 (3)
C17—C12—C5—C4	−106.18 (15)	C26—O4—C27—C28	−88.67 (19)
N1—C5—C4—C3	−37.21 (18)	C12—C17—C16—C15	−1.2 (3)
C12—C5—C4—C3	−162.89 (13)	C12—C13—C14—C15	−0.4 (3)
N1—C5—C4—C19	−164.62 (14)	C13—C14—C15—C16	1.1 (3)
C12—C5—C4—C19	69.69 (17)	C17—C16—C15—C14	−0.4 (3)
C21—N2—C22—C23	−178.42 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2	0.98	2.51	3.1788 (17)	125
C8—H8···O2i	0.93	2.54	3.4406 (19)	162
C24—H24A···O1ii	0.97	2.56	3.520 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2	0.98	2.51	3.1788 (17)	125
C8—H8⋯O2i	0.93	2.54	3.4406 (19)	162
C24—H24A⋯O1ii	0.97	2.56	3.520 (2)	169

Symmetry codes: (i) ; (ii) .