Paraherquamide e.

In the title compound, C(28)H(35)N(3)O(4), also known as 14-de-oxy-paraherquamide A,the two pyrrolidine rings adopt envelope conformations. The piperazine ring of the diaza-bicyclo-[2.2.2]octan-3-one unit adopts a boat conformation whereas the two piperidine rings are in distorted boat conformations. Intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, the mol-ecules are linked into chains along the b axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the structure determination of paraherquamides, see: Liesch & Wichmann (1990 ▶). For the crystal structure of paraherquamide A, see: Yamazaki et al. (1981 ▶). For the anti­nematodal and anti­parasitic activities of paraherquamides, see: Ondeyka et al. (1990 ▶). For their anthelmintic activity, see: Blanchflower et al. (1991 ▶) and for their insecticidal activity, see: Lopez-Gresa et al. (2006 ▶). For reviews on the total synthesis and biosynthesis of paraherquamides, see: Williams (2002 ▶); Williams & Cox (2003 ▶).

Experimental

Crystal data

C28H35N3O4

M = 477.59

Orthorhombic,

a = 6.5069 (2) Å

b = 16.0351 (8) Å

c = 23.9713 (11) Å

V = 2501.14 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.946, T max = 0.954

8444 measured reflections

2889 independent reflections

1746 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.102

S = 0.98

2889 reflections

322 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al. 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030795/ci5149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030795/ci5149Isup2.hkl

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

C28H35N3O4	Dx = 1.268 Mg m−3
Mr = 477.59	Melting point: not measured K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1372 reflections
a = 6.5069 (2) Å	θ = 2.5–19.7°
b = 16.0351 (8) Å	µ = 0.09 mm−1
c = 23.9713 (11) Å	T = 298 K
V = 2501.14 (19) Å3	Needle, colourless
Z = 4	0.40 × 0.10 × 0.10 mm
F(000) = 1024

Bruker SMART APEXII CCD area-detector diffractometer	2889 independent reflections
Radiation source: fine-focus sealed tube	1746 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 28.2°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→8
Tmin = 0.946, Tmax = 0.954	k = −20→15
8444 measured reflections	l = −31→26

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) = 0.102	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0463P)2] where P = (Fo2 + 2Fc2)/3
2889 reflections	(Δ/σ)max = 0.001
322 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 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
N1	0.0595 (4)	0.84401 (16)	0.16792 (11)	0.0366 (7)
H1	−0.0514	0.8699	0.1769	0.044*
N2	0.6009 (5)	0.47354 (18)	0.15605 (13)	0.0452 (8)
N3	0.3520 (4)	0.54738 (18)	0.23432 (11)	0.0353 (7)
O1	−0.0133 (4)	0.71770 (14)	0.20826 (10)	0.0510 (7)
O2	0.4573 (4)	1.06380 (14)	0.07563 (9)	0.0421 (7)
O3	0.0828 (4)	1.01425 (14)	0.13216 (10)	0.0468 (7)
O4	0.2499 (4)	0.41513 (15)	0.25453 (10)	0.0543 (7)
C2	0.0988 (6)	0.7623 (2)	0.17997 (14)	0.0364 (9)
C3	0.3025 (5)	0.73668 (19)	0.15236 (13)	0.0293 (8)
C4	0.5582 (5)	0.8436 (2)	0.10529 (14)	0.0387 (9)
H4	0.6645	0.8054	0.1007	0.046*
C5	0.5796 (5)	0.9252 (2)	0.08689 (14)	0.0396 (9)
H5	0.7014	0.9414	0.0697	0.047*
C6	0.4235 (5)	0.9831 (2)	0.09359 (13)	0.0336 (8)
C7	0.2432 (6)	0.9606 (2)	0.12015 (14)	0.0327 (8)
C8	0.2239 (5)	0.8798 (2)	0.13901 (14)	0.0314 (8)
C9	0.3764 (5)	0.8200 (2)	0.13052 (13)	0.0321 (8)
C10	0.4413 (6)	0.6932 (2)	0.19609 (14)	0.0393 (9)
H10A	0.5828	0.7110	0.1916	0.047*
H10B	0.3968	0.7074	0.2335	0.047*
C11	0.4239 (5)	0.5991 (2)	0.18678 (12)	0.0308 (8)
C12	0.6319 (5)	0.5608 (2)	0.17134 (15)	0.0434 (10)
H12A	0.6918	0.5910	0.1403	0.052*
H12B	0.7252	0.5646	0.2028	0.052*
C13	0.3851 (5)	0.4474 (2)	0.16074 (14)	0.0353 (9)
C14	0.4053 (6)	0.3551 (2)	0.14645 (17)	0.0553 (11)
H14	0.4357	0.3520	0.1065	0.066*
C15	0.6035 (8)	0.3309 (3)	0.1771 (2)	0.0952 (18)
H15A	0.5717	0.3047	0.2126	0.114*
H15B	0.6839	0.2923	0.1549	0.114*
C16	0.7211 (7)	0.4117 (3)	0.1863 (2)	0.0831 (16)
H16A	0.7289	0.4254	0.2256	0.100*
H16B	0.8593	0.4078	0.1713	0.100*
C17	0.2264 (8)	0.2967 (2)	0.15698 (19)	0.0720 (14)
H17A	0.1929	0.2970	0.1960	0.108*
H17B	0.2634	0.2412	0.1458	0.108*
H17C	0.1094	0.3149	0.1358	0.108*
C18	0.3167 (5)	0.4666 (2)	0.22117 (14)	0.0377 (9)
C19	0.2626 (6)	0.50045 (19)	0.11950 (13)	0.0371 (9)
H19A	0.1244	0.4786	0.1156	0.045*
H19B	0.3282	0.4998	0.0832	0.045*
C20	0.2558 (5)	0.58959 (18)	0.14247 (12)	0.0282 (8)
H20	0.1259	0.5933	0.1630	0.034*
C21	0.2623 (5)	0.66842 (19)	0.10578 (13)	0.0311 (8)
C22	0.4342 (6)	0.6665 (2)	0.06154 (14)	0.0441 (10)
H22A	0.5655	0.6642	0.0798	0.066*
H22B	0.4266	0.7159	0.0390	0.066*
H22C	0.4175	0.6182	0.0383	0.066*
C23	0.0595 (6)	0.6830 (2)	0.07491 (15)	0.0463 (10)
H23A	0.0437	0.6417	0.0462	0.069*
H23B	0.0603	0.7375	0.0584	0.069*
H23C	−0.0527	0.6788	0.1008	0.069*
C24	0.0153 (6)	1.0726 (2)	0.09430 (16)	0.0498 (10)
H24	−0.1173	1.0923	0.1003	0.060*
C25	0.1105 (6)	1.1046 (2)	0.05100 (17)	0.0523 (11)
H25	0.0318	1.1411	0.0298	0.063*
C26	0.3240 (6)	1.0919 (2)	0.03039 (14)	0.0456 (10)
C27	0.4195 (8)	1.1744 (2)	0.0128 (2)	0.0788 (15)
H27A	0.4292	1.2107	0.0446	0.118*
H27B	0.3351	1.2001	−0.0152	0.118*
H27C	0.5543	1.1646	−0.0021	0.118*
C28	0.3285 (7)	1.0286 (3)	−0.01689 (16)	0.0696 (14)
H28A	0.4682	1.0189	−0.0280	0.104*
H28B	0.2518	1.0497	−0.0480	0.104*
H28C	0.2685	0.9771	−0.0044	0.104*
C29	0.3185 (8)	0.5797 (3)	0.28994 (15)	0.0709 (14)
H29A	0.2896	0.5344	0.3149	0.106*
H29B	0.2042	0.6175	0.2895	0.106*
H29C	0.4394	0.6086	0.3023	0.106*

	U11	U22	U33	U12	U13	U23
N1	0.0304 (16)	0.0298 (18)	0.0497 (17)	0.0040 (13)	0.0168 (14)	0.0009 (14)
N2	0.0426 (19)	0.0366 (19)	0.056 (2)	0.0087 (16)	0.0165 (16)	0.0203 (16)
N3	0.0423 (18)	0.0410 (19)	0.0227 (14)	−0.0021 (14)	0.0018 (13)	0.0055 (13)
O1	0.0489 (17)	0.0379 (16)	0.0663 (17)	−0.0022 (12)	0.0272 (14)	0.0053 (13)
O2	0.0468 (16)	0.0336 (15)	0.0457 (15)	−0.0107 (12)	−0.0008 (13)	0.0057 (12)
O3	0.0510 (16)	0.0383 (15)	0.0513 (15)	0.0103 (13)	0.0191 (13)	0.0106 (13)
O4	0.0655 (18)	0.0513 (16)	0.0460 (16)	−0.0100 (15)	0.0173 (14)	0.0181 (14)
C2	0.037 (2)	0.032 (2)	0.040 (2)	−0.0045 (18)	0.0061 (18)	−0.0024 (17)
C3	0.0302 (19)	0.0281 (19)	0.0296 (18)	−0.0024 (15)	0.0045 (16)	0.0010 (15)
C4	0.027 (2)	0.037 (2)	0.052 (2)	−0.0009 (16)	0.0052 (18)	−0.0025 (18)
C5	0.027 (2)	0.042 (2)	0.050 (2)	−0.0092 (19)	0.0052 (18)	−0.0007 (18)
C6	0.037 (2)	0.029 (2)	0.0343 (19)	−0.0059 (18)	0.0019 (18)	0.0009 (16)
C7	0.036 (2)	0.025 (2)	0.0365 (19)	0.0032 (17)	0.0030 (17)	−0.0035 (15)
C8	0.0300 (19)	0.031 (2)	0.0329 (19)	−0.0055 (16)	0.0043 (16)	−0.0063 (16)
C9	0.032 (2)	0.032 (2)	0.0316 (18)	−0.0039 (17)	0.0001 (17)	−0.0014 (16)
C10	0.035 (2)	0.043 (2)	0.040 (2)	−0.0051 (17)	−0.0061 (17)	−0.0005 (17)
C11	0.0298 (19)	0.035 (2)	0.0275 (17)	−0.0047 (16)	−0.0012 (16)	0.0076 (15)
C12	0.029 (2)	0.051 (3)	0.050 (2)	0.0013 (17)	−0.0004 (18)	0.0189 (19)
C13	0.039 (2)	0.029 (2)	0.038 (2)	0.0025 (16)	0.0131 (18)	0.0098 (17)
C14	0.069 (3)	0.034 (2)	0.063 (3)	0.010 (2)	0.024 (2)	0.011 (2)
C15	0.083 (4)	0.055 (3)	0.148 (5)	0.026 (3)	0.021 (4)	0.048 (3)
C16	0.056 (3)	0.065 (3)	0.129 (4)	0.022 (3)	0.012 (3)	0.046 (3)
C17	0.093 (4)	0.040 (2)	0.083 (3)	−0.002 (2)	0.023 (3)	0.002 (2)
C18	0.032 (2)	0.042 (2)	0.040 (2)	0.0033 (17)	0.0061 (17)	0.0121 (19)
C19	0.052 (2)	0.031 (2)	0.0282 (18)	0.0012 (18)	0.0014 (18)	0.0000 (16)
C20	0.0256 (17)	0.0321 (19)	0.0269 (18)	−0.0008 (15)	0.0028 (15)	0.0017 (15)
C21	0.0311 (19)	0.035 (2)	0.0272 (18)	−0.0002 (16)	−0.0017 (16)	0.0050 (15)
C22	0.055 (3)	0.041 (2)	0.036 (2)	0.005 (2)	0.0101 (19)	0.0052 (17)
C23	0.046 (2)	0.043 (2)	0.050 (2)	0.000 (2)	−0.0187 (19)	0.0070 (18)
C24	0.047 (2)	0.038 (2)	0.065 (3)	0.0089 (19)	0.015 (2)	0.007 (2)
C25	0.053 (3)	0.049 (3)	0.055 (2)	0.008 (2)	0.005 (2)	0.013 (2)
C26	0.051 (2)	0.045 (2)	0.040 (2)	0.0019 (19)	0.010 (2)	0.0102 (19)
C27	0.084 (4)	0.052 (3)	0.100 (4)	−0.003 (3)	0.019 (3)	0.037 (3)
C28	0.081 (4)	0.087 (3)	0.041 (2)	0.016 (3)	0.003 (2)	−0.003 (2)
C29	0.120 (4)	0.064 (3)	0.029 (2)	−0.019 (3)	0.012 (2)	0.004 (2)

N1—C2	1.366 (4)	C14—C15	1.534 (6)
N1—C8	1.398 (4)	C14—H14	0.98
N1—H1	0.86	C15—C16	1.521 (7)
N2—C16	1.456 (5)	C15—H15A	0.97
N2—C12	1.460 (4)	C15—H15B	0.97
N2—C13	1.470 (5)	C16—H16A	0.97
N3—C18	1.353 (4)	C16—H16B	0.97
N3—C29	1.447 (4)	C17—H17A	0.96
N3—C11	1.485 (4)	C17—H17B	0.96
O1—C2	1.226 (4)	C17—H17C	0.96
O2—C6	1.382 (4)	C19—C20	1.532 (4)
O2—C26	1.460 (4)	C19—H19A	0.97
O3—C24	1.376 (4)	C19—H19B	0.97
O3—C7	1.383 (4)	C20—C21	1.541 (4)
O4—C18	1.228 (4)	C20—H20	0.98
C2—C3	1.537 (5)	C21—C23	1.531 (5)
C3—C9	1.513 (4)	C21—C22	1.541 (5)
C3—C10	1.550 (4)	C22—H22A	0.96
C3—C21	1.585 (4)	C22—H22B	0.96
C4—C9	1.382 (5)	C22—H22C	0.96
C4—C5	1.388 (4)	C23—H23A	0.96
C4—H4	0.93	C23—H23B	0.96
C5—C6	1.385 (5)	C23—H23C	0.96
C5—H5	0.93	C24—C25	1.313 (5)
C6—C7	1.382 (5)	C24—H24	0.93
C7—C8	1.378 (4)	C25—C26	1.489 (5)
C8—C9	1.395 (5)	C25—H25	0.93
C10—C11	1.529 (5)	C26—C28	1.522 (5)
C10—H10A	0.97	C26—C27	1.522 (5)
C10—H10B	0.97	C27—H27A	0.96
C11—C12	1.532 (5)	C27—H27B	0.96
C11—C20	1.533 (4)	C27—H27C	0.96
C12—H12A	0.97	C28—H28A	0.96
C12—H12B	0.97	C28—H28B	0.96
C13—C14	1.525 (5)	C28—H28C	0.96
C13—C19	1.528 (5)	C29—H29A	0.96
C13—C18	1.546 (5)	C29—H29B	0.96
C14—C17	1.516 (6)	C29—H29C	0.96
C2—N1—C8	110.8 (3)	N2—C16—H16A	111.0
C2—N1—H1	124.6	C15—C16—H16A	111.0
C8—N1—H1	124.6	N2—C16—H16B	111.0
C16—N2—C12	117.0 (3)	C15—C16—H16B	111.0
C16—N2—C13	106.3 (3)	H16A—C16—H16B	109.0
C12—N2—C13	112.7 (3)	C14—C17—H17A	109.5
C18—N3—C29	122.1 (3)	C14—C17—H17B	109.5
C18—N3—C11	114.2 (3)	H17A—C17—H17B	109.5
C29—N3—C11	123.7 (3)	C14—C17—H17C	109.5
C6—O2—C26	115.2 (3)	H17A—C17—H17C	109.5
C24—O3—C7	121.8 (3)	H17B—C17—H17C	109.5
O1—C2—N1	124.4 (3)	O4—C18—N3	123.5 (3)
O1—C2—C3	126.5 (3)	O4—C18—C13	125.3 (3)
N1—C2—C3	109.1 (3)	N3—C18—C13	111.1 (3)
C9—C3—C2	100.8 (3)	C13—C19—C20	107.6 (3)
C9—C3—C10	116.5 (3)	C13—C19—H19A	110.2
C2—C3—C10	109.4 (3)	C20—C19—H19A	110.2
C9—C3—C21	114.7 (2)	C13—C19—H19B	110.2
C2—C3—C21	110.2 (3)	C20—C19—H19B	110.2
C10—C3—C21	105.2 (2)	H19A—C19—H19B	108.5
C9—C4—C5	118.9 (3)	C19—C20—C11	108.8 (3)
C9—C4—H4	120.6	C19—C20—C21	124.0 (3)
C5—C4—H4	120.6	C11—C20—C21	107.1 (2)
C6—C5—C4	121.4 (3)	C19—C20—H20	105.2
C6—C5—H5	119.3	C11—C20—H20	105.2
C4—C5—H5	119.3	C21—C20—H20	105.2
O2—C6—C7	121.5 (3)	C23—C21—C20	112.2 (3)
O2—C6—C5	118.3 (3)	C23—C21—C22	107.2 (3)
C7—C6—C5	120.1 (3)	C20—C21—C22	113.4 (3)
C8—C7—C6	118.3 (3)	C23—C21—C3	112.2 (3)
C8—C7—O3	116.6 (3)	C20—C21—C3	99.7 (2)
C6—C7—O3	125.1 (3)	C22—C21—C3	112.3 (3)
C7—C8—C9	122.3 (3)	C21—C22—H22A	109.5
C7—C8—N1	128.2 (3)	C21—C22—H22B	109.5
C9—C8—N1	109.5 (3)	H22A—C22—H22B	109.5
C4—C9—C8	119.0 (3)	C21—C22—H22C	109.5
C4—C9—C3	131.7 (3)	H22A—C22—H22C	109.5
C8—C9—C3	109.3 (3)	H22B—C22—H22C	109.5
C11—C10—C3	107.6 (3)	C21—C23—H23A	109.5
C11—C10—H10A	110.2	C21—C23—H23B	109.5
C3—C10—H10A	110.2	H23A—C23—H23B	109.5
C11—C10—H10B	110.2	C21—C23—H23C	109.5
C3—C10—H10B	110.2	H23A—C23—H23C	109.5
H10A—C10—H10B	108.5	H23B—C23—H23C	109.5
N3—C11—C10	117.5 (3)	C25—C24—O3	129.5 (4)
N3—C11—C12	103.8 (3)	C25—C24—H24	115.2
C10—C11—C12	111.5 (3)	O3—C24—H24	115.2
N3—C11—C20	104.5 (2)	C24—C25—C26	130.5 (4)
C10—C11—C20	104.6 (3)	C24—C25—H25	114.8
C12—C11—C20	115.0 (3)	C26—C25—H25	114.8
N2—C12—C11	108.9 (3)	O2—C26—C25	110.5 (3)
N2—C12—H12A	109.9	O2—C26—C28	109.7 (3)
C11—C12—H12A	109.9	C25—C26—C28	110.9 (3)
N2—C12—H12B	109.9	O2—C26—C27	103.4 (3)
C11—C12—H12B	109.9	C25—C26—C27	110.7 (3)
H12A—C12—H12B	108.3	C28—C26—C27	111.5 (3)
N2—C13—C14	100.2 (3)	C26—C27—H27A	109.5
N2—C13—C19	106.9 (3)	C26—C27—H27B	109.5
C14—C13—C19	116.1 (3)	H27A—C27—H27B	109.5
N2—C13—C18	106.9 (3)	C26—C27—H27C	109.5
C14—C13—C18	115.3 (3)	H27A—C27—H27C	109.5
C19—C13—C18	110.2 (3)	H27B—C27—H27C	109.5
C17—C14—C13	119.7 (3)	C26—C28—H28A	109.5
C17—C14—C15	114.2 (3)	C26—C28—H28B	109.5
C13—C14—C15	102.1 (4)	H28A—C28—H28B	109.5
C17—C14—H14	106.7	C26—C28—H28C	109.5
C13—C14—H14	106.7	H28A—C28—H28C	109.5
C15—C14—H14	106.7	H28B—C28—H28C	109.5
C16—C15—C14	106.0 (3)	N3—C29—H29A	109.5
C16—C15—H15A	110.5	N3—C29—H29B	109.5
C14—C15—H15A	110.5	H29A—C29—H29B	109.5
C16—C15—H15B	110.5	N3—C29—H29C	109.5
C14—C15—H15B	110.5	H29A—C29—H29C	109.5
H15A—C15—H15B	108.7	H29B—C29—H29C	109.5
N2—C16—C15	103.8 (4)
C8—N1—C2—O1	174.9 (3)	C16—N2—C13—C18	73.7 (4)
C8—N1—C2—C3	−5.3 (4)	C12—N2—C13—C18	−55.7 (3)
O1—C2—C3—C9	−173.3 (3)	N2—C13—C14—C17	167.8 (4)
N1—C2—C3—C9	7.0 (3)	C19—C13—C14—C17	−77.6 (5)
O1—C2—C3—C10	−50.0 (4)	C18—C13—C14—C17	53.5 (5)
N1—C2—C3—C10	130.2 (3)	N2—C13—C14—C15	40.5 (4)
O1—C2—C3—C21	65.1 (4)	C19—C13—C14—C15	155.1 (3)
N1—C2—C3—C21	−114.6 (3)	C18—C13—C14—C15	−73.7 (4)
C9—C4—C5—C6	0.3 (5)	C17—C14—C15—C16	−152.3 (4)
C26—O2—C6—C7	−66.8 (4)	C13—C14—C15—C16	−21.5 (5)
C26—O2—C6—C5	116.4 (3)	C12—N2—C16—C15	160.1 (3)
C4—C5—C6—O2	178.3 (3)	C13—N2—C16—C15	33.2 (4)
C4—C5—C6—C7	1.4 (5)	C14—C15—C16—N2	−6.0 (5)
O2—C6—C7—C8	−177.3 (3)	C29—N3—C18—O4	1.6 (5)
C5—C6—C7—C8	−0.5 (5)	C11—N3—C18—O4	−177.4 (3)
O2—C6—C7—O3	−0.9 (5)	C29—N3—C18—C13	−174.5 (3)
C5—C6—C7—O3	175.9 (3)	C11—N3—C18—C13	6.5 (4)
C24—O3—C7—C8	−141.1 (3)	N2—C13—C18—O4	−121.8 (4)
C24—O3—C7—C6	42.5 (5)	C14—C13—C18—O4	−11.4 (5)
C6—C7—C8—C9	−2.2 (5)	C19—C13—C18—O4	122.4 (4)
O3—C7—C8—C9	−178.8 (3)	N2—C13—C18—N3	54.3 (3)
C6—C7—C8—N1	178.3 (3)	C14—C13—C18—N3	164.6 (3)
O3—C7—C8—N1	1.6 (5)	C19—C13—C18—N3	−61.5 (4)
C2—N1—C8—C7	−179.3 (3)	N2—C13—C19—C20	−70.9 (3)
C2—N1—C8—C9	1.1 (4)	C14—C13—C19—C20	178.3 (3)
C5—C4—C9—C8	−2.9 (5)	C18—C13—C19—C20	44.8 (4)
C5—C4—C9—C3	176.9 (3)	C13—C19—C20—C11	17.3 (4)
C7—C8—C9—C4	3.9 (5)	C13—C19—C20—C21	144.4 (3)
N1—C8—C9—C4	−176.5 (3)	N3—C11—C20—C19	−69.8 (3)
C7—C8—C9—C3	−175.9 (3)	C10—C11—C20—C19	166.1 (3)
N1—C8—C9—C3	3.7 (4)	C12—C11—C20—C19	43.4 (4)
C2—C3—C9—C4	173.8 (3)	N3—C11—C20—C21	154.0 (3)
C10—C3—C9—C4	55.7 (5)	C10—C11—C20—C21	29.8 (3)
C21—C3—C9—C4	−67.8 (5)	C12—C11—C20—C21	−92.8 (3)
C2—C3—C9—C8	−6.3 (3)	C19—C20—C21—C23	73.5 (4)
C10—C3—C9—C8	−124.5 (3)	C11—C20—C21—C23	−158.6 (3)
C21—C3—C9—C8	112.1 (3)	C19—C20—C21—C22	−48.1 (4)
C9—C3—C10—C11	−146.2 (3)	C11—C20—C21—C22	79.8 (3)
C2—C3—C10—C11	100.4 (3)	C19—C20—C21—C3	−167.6 (3)
C21—C3—C10—C11	−18.0 (3)	C11—C20—C21—C3	−39.7 (3)
C18—N3—C11—C10	172.4 (3)	C9—C3—C21—C23	−77.2 (4)
C29—N3—C11—C10	−6.6 (5)	C2—C3—C21—C23	35.6 (4)
C18—N3—C11—C12	−64.0 (3)	C10—C3—C21—C23	153.4 (3)
C29—N3—C11—C12	117.0 (4)	C9—C3—C21—C20	163.9 (3)
C18—N3—C11—C20	57.0 (3)	C2—C3—C21—C20	−83.2 (3)
C29—N3—C11—C20	−122.0 (4)	C10—C3—C21—C20	34.5 (3)
C3—C10—C11—N3	−121.9 (3)	C9—C3—C21—C22	43.6 (4)
C3—C10—C11—C12	118.4 (3)	C2—C3—C21—C22	156.5 (3)
C3—C10—C11—C20	−6.5 (3)	C10—C3—C21—C22	−85.8 (3)
C16—N2—C12—C11	−124.8 (3)	C7—O3—C24—C25	−20.7 (6)
C13—N2—C12—C11	−1.1 (4)	O3—C24—C25—C26	−3.5 (7)
N3—C11—C12—N2	59.7 (3)	C6—O2—C26—C25	71.2 (4)
C10—C11—C12—N2	−172.8 (3)	C6—O2—C26—C28	−51.3 (4)
C20—C11—C12—N2	−53.9 (4)	C6—O2—C26—C27	−170.3 (3)
C16—N2—C13—C14	−46.9 (4)	C24—C25—C26—O2	−23.2 (6)
C12—N2—C13—C14	−176.3 (3)	C24—C25—C26—C28	98.6 (5)
C16—N2—C13—C19	−168.3 (3)	C24—C25—C26—C27	−137.2 (5)
C12—N2—C13—C19	62.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.86	2.21	2.968 (4)	147
C17—H17A···O4	0.96	2.39	3.016 (5)	123
C20—H20···O1	0.98	2.44	3.126 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.86	2.21	2.968 (4)	147
C17—H17A⋯O4	0.96	2.39	3.016 (5)	123
C20—H20⋯O1	0.98	2.44	3.126 (4)	126

Symmetry code: (i) .