N-Cyclo-hexyl-5H,7H-13,15-dimethyl-9-nitro-5-oxophenanthrido[4,4a,5-bc][1,4]benzoxazepine-7-carboxamide.

In the title compound, C(29)H(27)N(3)O(5), a dibenz[b,f][1,4]oxazepine derivative, the cyclo-hexane ring adopts a chair conformation, the oxazepine seven-membered ring has a twist-boat conformation, and the piperidin-2-one ring assumes a flattened boat conformation. Inter-molecular N-H⋯O hydrogen bonding between imino and nitro groups links two mol-ecules into a centrosymmetric dimer.

Related literature

For the biological activity of dibenz[b,f][1,4]oxazepines, see: Klunder et al. (1992 ▶); Merluzzi et al. (1990 ▶); Nagarajan et al. (1986 ▶); Hallinan et al. (1993 ▶, 1996 ▶). For our recent microwave-assisted synthesis of dibenz[b,f][1,4]oxazepines, see: Dai & Shi (2007 ▶); Xing et al. (2006 ▶). For microwave-assisted palladium-catalysed intra­molecular direct aryl­ation, see: Wu et al. (2007 ▶).

Experimental

Crystal data

C29H27N3O5

M = 497.54

Monoclinic,

a = 10.7451 (4) Å

b = 27.8791 (7) Å

c = 8.4917 (3) Å

β = 105.428 (13)°

V = 2452.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.28 × 0.26 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

23870 measured reflections

5594 independent reflections

3756 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.127

S = 1.00

5594 reflections

336 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028712/xu2558sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028712/xu2558Isup2.hkl

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

C29H27N3O5	F(000) = 1048
Mr = 497.54	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15928 reflections
a = 10.7451 (4) Å	θ = 3.1–27.5°
b = 27.8791 (7) Å	µ = 0.09 mm−1
c = 8.4917 (3) Å	T = 296 K
β = 105.428 (13)°	Chunk, yellow
V = 2452.1 (2) Å3	0.28 × 0.26 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3756 reflections with I > 2σ(I)
Radiation source: rolling anode	Rint = 0.054
graphite	θmax = 27.5°, θmin = 3.1°
Detector resolution: 10.00 pixels mm-1	h = −13→13
ω scans	k = −36→35
23870 measured reflections	l = −10→10
5594 independent 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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0432P)2 + 1P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
5594 reflections	Δρmax = 0.29 e Å−3
336 parameters	Δρmin = −0.23 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: 0.0051 (10)

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)
O2	0.52077 (12)	0.14876 (4)	0.75758 (15)	0.0441 (3)
N1	0.30895 (13)	0.12575 (5)	0.46737 (17)	0.0363 (3)
O5	0.53052 (13)	0.12552 (5)	0.37217 (15)	0.0509 (4)
C13	0.43278 (17)	0.18313 (6)	0.6721 (2)	0.0371 (4)
C14	0.32745 (16)	0.17213 (6)	0.5375 (2)	0.0355 (4)
N3	0.63285 (14)	0.07287 (6)	0.56536 (19)	0.0429 (4)
H3	0.6229	0.0498	0.6281	0.052*
C10	0.27335 (18)	0.25731 (7)	0.5195 (2)	0.0423 (4)
C9	0.23969 (17)	0.20945 (6)	0.4689 (2)	0.0383 (4)
C22	0.40912 (16)	0.07561 (6)	0.7002 (2)	0.0381 (4)
O1	0.20934 (15)	0.07613 (5)	0.25999 (19)	0.0654 (4)
C12	0.46090 (18)	0.22939 (7)	0.7269 (2)	0.0419 (4)
C1	0.40183 (16)	0.08658 (6)	0.5246 (2)	0.0364 (4)
H1	0.3657	0.0581	0.4615	0.044*
C16	0.76257 (17)	0.08427 (6)	0.5510 (2)	0.0406 (4)
H16	0.7586	0.0869	0.4347	0.049*
C3	0.10767 (18)	0.15002 (7)	0.2797 (2)	0.0437 (4)
C11	0.38132 (19)	0.26588 (7)	0.6456 (2)	0.0453 (4)
H11	0.4019	0.2974	0.6779	0.054*
C27	0.46631 (17)	0.10965 (7)	0.8143 (2)	0.0411 (4)
C15	0.52969 (17)	0.09773 (6)	0.4828 (2)	0.0378 (4)
C2	0.21089 (18)	0.11460 (7)	0.3296 (2)	0.0440 (4)
N2	0.3006 (2)	−0.01158 (8)	0.9665 (3)	0.0698 (6)
C8	0.11937 (18)	0.19597 (7)	0.3490 (2)	0.0430 (4)
C23	0.35448 (18)	0.03542 (7)	0.7497 (2)	0.0455 (5)
H23	0.3150	0.0120	0.6749	0.055*
C24	0.3602 (2)	0.03099 (8)	0.9136 (3)	0.0521 (5)
C26	0.4739 (2)	0.10462 (8)	0.9787 (2)	0.0531 (5)
H26	0.5151	0.1276	1.0540	0.064*
O3	0.3241 (2)	−0.01856 (7)	1.1134 (2)	0.0931 (7)
C25	0.4187 (2)	0.06458 (8)	1.0275 (3)	0.0581 (6)
H25	0.4211	0.0604	1.1369	0.070*
C4	−0.0059 (2)	0.13491 (9)	0.1673 (3)	0.0583 (6)
H4	−0.0109	0.1043	0.1223	0.070*
C28	0.2043 (2)	0.30111 (7)	0.4341 (3)	0.0576 (5)
H28A	0.1288	0.3071	0.4712	0.086*
H28B	0.1793	0.2957	0.3183	0.086*
H28C	0.2609	0.3283	0.4585	0.086*
C29	0.5782 (2)	0.24052 (8)	0.8644 (3)	0.0555 (5)
H29A	0.5820	0.2744	0.8856	0.067*	0.50
H29B	0.6544	0.2307	0.8345	0.067*	0.50
H29C	0.5729	0.2236	0.9608	0.067*	0.50
H29D	0.6243	0.2114	0.9017	0.067*	0.50
H29E	0.5518	0.2551	0.9528	0.067*	0.50
H29F	0.6333	0.2622	0.8265	0.067*	0.50
C21	0.8092 (2)	0.13172 (8)	0.6321 (3)	0.0585 (6)
H21A	0.8113	0.1302	0.7469	0.070*
H21B	0.7498	0.1570	0.5819	0.070*
C7	0.0090 (2)	0.22515 (8)	0.3054 (3)	0.0586 (6)
H7	0.0109	0.2553	0.3529	0.070*
C19	1.0384 (2)	0.10368 (9)	0.6890 (3)	0.0697 (7)
H19A	1.1223	0.1111	0.6728	0.084*
H19B	1.0475	0.1017	0.8055	0.084*
C18	0.9917 (2)	0.05620 (8)	0.6100 (3)	0.0624 (6)
H18A	1.0508	0.0311	0.6621	0.075*
H18B	0.9910	0.0573	0.4956	0.075*
O4	0.2348 (2)	−0.03785 (8)	0.8627 (3)	0.1074 (8)
C17	0.85656 (19)	0.04450 (8)	0.6240 (3)	0.0560 (5)
H17A	0.8275	0.0146	0.5676	0.067*
H17B	0.8588	0.0403	0.7382	0.067*
C5	−0.1100 (2)	0.16528 (10)	0.1235 (3)	0.0711 (7)
H5	−0.1851	0.1557	0.0470	0.085*
C6	−0.1020 (2)	0.21008 (10)	0.1942 (3)	0.0717 (7)
H6	−0.1729	0.2305	0.1661	0.086*
C20	0.9432 (2)	0.14320 (9)	0.6151 (4)	0.0747 (7)
H20A	0.9397	0.1468	0.5004	0.090*
H20B	0.9725	0.1733	0.6696	0.090*

	U11	U22	U33	U12	U13	U23
O2	0.0353 (7)	0.0476 (7)	0.0436 (7)	0.0026 (6)	0.0003 (6)	0.0016 (6)
N1	0.0318 (7)	0.0418 (8)	0.0331 (7)	0.0010 (6)	0.0050 (6)	−0.0007 (6)
O5	0.0476 (8)	0.0657 (9)	0.0409 (7)	0.0051 (7)	0.0144 (6)	0.0145 (7)
C13	0.0336 (9)	0.0430 (9)	0.0344 (9)	0.0014 (7)	0.0084 (7)	0.0016 (7)
C14	0.0333 (9)	0.0417 (9)	0.0324 (8)	−0.0011 (7)	0.0104 (7)	0.0008 (7)
N3	0.0347 (8)	0.0480 (9)	0.0470 (9)	0.0021 (7)	0.0125 (7)	0.0101 (7)
C10	0.0417 (10)	0.0443 (10)	0.0441 (10)	0.0042 (8)	0.0169 (9)	0.0052 (8)
C9	0.0356 (9)	0.0453 (10)	0.0349 (9)	0.0020 (8)	0.0111 (7)	0.0045 (7)
C22	0.0305 (9)	0.0470 (10)	0.0362 (9)	0.0065 (8)	0.0075 (7)	0.0064 (8)
O1	0.0584 (9)	0.0635 (9)	0.0603 (9)	0.0070 (8)	−0.0088 (7)	−0.0223 (8)
C12	0.0398 (10)	0.0487 (10)	0.0381 (9)	−0.0044 (8)	0.0122 (8)	−0.0032 (8)
C1	0.0348 (9)	0.0392 (9)	0.0334 (8)	0.0006 (7)	0.0059 (7)	0.0002 (7)
C16	0.0346 (9)	0.0459 (10)	0.0425 (10)	−0.0002 (8)	0.0126 (8)	0.0001 (8)
C3	0.0342 (10)	0.0584 (11)	0.0356 (9)	0.0001 (8)	0.0044 (8)	0.0035 (8)
C11	0.0486 (11)	0.0430 (10)	0.0462 (10)	−0.0027 (9)	0.0157 (9)	−0.0042 (8)
C27	0.0354 (9)	0.0495 (10)	0.0372 (9)	0.0088 (8)	0.0077 (8)	0.0050 (8)
C15	0.0377 (10)	0.0432 (10)	0.0323 (9)	−0.0003 (8)	0.0088 (7)	−0.0010 (7)
C2	0.0380 (10)	0.0523 (11)	0.0384 (9)	−0.0018 (8)	0.0047 (8)	−0.0022 (8)
N2	0.0618 (13)	0.0776 (14)	0.0797 (15)	0.0213 (11)	0.0359 (12)	0.0415 (12)
C8	0.0364 (10)	0.0525 (11)	0.0400 (10)	0.0029 (8)	0.0103 (8)	0.0088 (8)
C23	0.0352 (10)	0.0522 (11)	0.0487 (11)	0.0043 (8)	0.0106 (8)	0.0113 (9)
C24	0.0451 (11)	0.0619 (13)	0.0548 (12)	0.0168 (10)	0.0229 (10)	0.0215 (10)
C26	0.0589 (13)	0.0615 (13)	0.0362 (10)	0.0213 (11)	0.0078 (9)	0.0017 (9)
O3	0.1025 (15)	0.1061 (15)	0.0891 (13)	0.0394 (12)	0.0579 (12)	0.0579 (11)
C25	0.0669 (14)	0.0724 (14)	0.0402 (11)	0.0292 (12)	0.0234 (10)	0.0174 (10)
C4	0.0450 (12)	0.0729 (14)	0.0485 (11)	−0.0028 (11)	−0.0022 (9)	−0.0050 (10)
C28	0.0593 (13)	0.0470 (11)	0.0654 (13)	0.0083 (10)	0.0145 (11)	0.0086 (10)
C29	0.0500 (12)	0.0595 (12)	0.0526 (12)	−0.0089 (10)	0.0061 (10)	−0.0104 (10)
C21	0.0457 (12)	0.0549 (12)	0.0732 (14)	0.0015 (10)	0.0132 (11)	−0.0130 (11)
C7	0.0457 (12)	0.0596 (13)	0.0654 (14)	0.0090 (10)	0.0059 (11)	0.0089 (11)
C19	0.0393 (12)	0.0793 (16)	0.0898 (17)	−0.0087 (11)	0.0158 (12)	−0.0193 (14)
C18	0.0400 (11)	0.0662 (14)	0.0813 (16)	0.0054 (10)	0.0168 (11)	−0.0123 (12)
O4	0.1032 (17)	0.1027 (16)	0.1141 (18)	−0.0339 (14)	0.0253 (14)	0.0357 (14)
C17	0.0417 (11)	0.0503 (12)	0.0751 (15)	0.0034 (9)	0.0140 (10)	0.0007 (10)
C5	0.0402 (12)	0.0983 (19)	0.0620 (14)	0.0048 (12)	−0.0087 (11)	0.0015 (14)
C6	0.0434 (13)	0.0856 (18)	0.0755 (16)	0.0171 (12)	−0.0030 (12)	0.0097 (14)
C20	0.0544 (14)	0.0601 (14)	0.108 (2)	−0.0151 (11)	0.0187 (14)	−0.0168 (14)

O2—C27	1.383 (2)	C23—C24	1.382 (3)
O2—C13	1.405 (2)	C23—H23	0.9300
N1—C2	1.386 (2)	C24—C25	1.373 (3)
N1—C14	1.415 (2)	C26—C25	1.379 (3)
N1—C1	1.472 (2)	C26—H26	0.9300
O5—C15	1.219 (2)	C25—H25	0.9300
C13—C12	1.377 (2)	C4—C5	1.373 (3)
C13—C14	1.412 (2)	C4—H4	0.9300
C14—C9	1.421 (2)	C28—H28A	0.9600
N3—C15	1.337 (2)	C28—H28B	0.9600
N3—C16	1.466 (2)	C28—H28C	0.9600
N3—H3	0.8600	C29—H29A	0.9600
C10—C11	1.374 (3)	C29—H29B	0.9600
C10—C9	1.419 (3)	C29—H29C	0.9600
C10—C28	1.510 (3)	C29—H29D	0.9600
C9—C8	1.466 (3)	C29—H29E	0.9600
C22—C27	1.378 (3)	C29—H29F	0.9600
C22—C23	1.381 (3)	C21—C20	1.519 (3)
C22—C1	1.503 (2)	C21—H21A	0.9700
O1—C2	1.223 (2)	C21—H21B	0.9700
C12—C11	1.389 (3)	C7—C6	1.375 (3)
C12—C29	1.505 (3)	C7—H7	0.9300
C1—C15	1.540 (2)	C19—C18	1.508 (3)
C1—H1	0.9800	C19—C20	1.521 (4)
C16—C21	1.514 (3)	C19—H19A	0.9700
C16—C17	1.517 (3)	C19—H19B	0.9700
C16—H16	0.9800	C18—C17	1.524 (3)
C3—C4	1.400 (3)	C18—H18A	0.9700
C3—C8	1.401 (3)	C18—H18B	0.9700
C3—C2	1.461 (3)	C17—H17A	0.9700
C11—H11	0.9300	C17—H17B	0.9700
C27—C26	1.384 (3)	C5—C6	1.378 (4)
N2—O4	1.217 (3)	C5—H5	0.9300
N2—O3	1.221 (3)	C6—H6	0.9300
N2—C24	1.474 (3)	C20—H20A	0.9700
C8—C7	1.404 (3)	C20—H20B	0.9700
C27—O2—C13	115.38 (13)	C5—C4—C3	119.9 (2)
C2—N1—C14	123.40 (15)	C5—C4—H4	120.0
C2—N1—C1	114.14 (14)	C3—C4—H4	120.0
C14—N1—C1	122.12 (13)	C10—C28—H28A	109.5
C12—C13—O2	114.03 (15)	C10—C28—H28B	109.5
C12—C13—C14	122.24 (16)	H28A—C28—H28B	109.5
O2—C13—C14	123.68 (15)	C10—C28—H28C	109.5
C13—C14—N1	122.13 (15)	H28A—C28—H28C	109.5
C13—C14—C9	118.32 (16)	H28B—C28—H28C	109.5
N1—C14—C9	119.54 (15)	C12—C29—H29A	109.5
C15—N3—C16	121.20 (15)	C12—C29—H29B	109.5
C15—N3—H3	119.4	H29A—C29—H29B	109.5
C16—N3—H3	119.4	C12—C29—H29C	109.5
C11—C10—C9	119.59 (17)	H29A—C29—H29C	109.5
C11—C10—C28	116.01 (18)	H29B—C29—H29C	109.5
C9—C10—C28	124.19 (18)	C12—C29—H29D	109.5
C14—C9—C10	118.47 (16)	H29A—C29—H29D	141.1
C14—C9—C8	117.61 (16)	H29B—C29—H29D	56.3
C10—C9—C8	123.91 (16)	H29C—C29—H29D	56.3
C27—C22—C23	119.37 (17)	C12—C29—H29E	109.5
C27—C22—C1	116.93 (16)	H29A—C29—H29E	56.3
C23—C22—C1	123.55 (17)	H29B—C29—H29E	141.1
C13—C12—C11	117.88 (17)	H29C—C29—H29E	56.3
C13—C12—C29	121.21 (17)	H29D—C29—H29E	109.5
C11—C12—C29	120.83 (17)	C12—C29—H29F	109.5
N1—C1—C22	109.29 (14)	H29A—C29—H29F	56.3
N1—C1—C15	110.02 (14)	H29B—C29—H29F	56.3
C22—C1—C15	117.11 (14)	H29C—C29—H29F	141.1
N1—C1—H1	106.6	H29D—C29—H29F	109.5
C22—C1—H1	106.6	H29E—C29—H29F	109.5
C15—C1—H1	106.6	C16—C21—C20	110.38 (18)
N3—C16—C21	110.99 (15)	C16—C21—H21A	109.6
N3—C16—C17	110.60 (15)	C20—C21—H21A	109.6
C21—C16—C17	110.42 (17)	C16—C21—H21B	109.6
N3—C16—H16	108.2	C20—C21—H21B	109.6
C21—C16—H16	108.2	H21A—C21—H21B	108.1
C17—C16—H16	108.2	C6—C7—C8	121.4 (2)
C4—C3—C8	121.73 (18)	C6—C7—H7	119.3
C4—C3—C2	116.84 (18)	C8—C7—H7	119.3
C8—C3—C2	121.33 (16)	C18—C19—C20	110.2 (2)
C10—C11—C12	122.71 (18)	C18—C19—H19A	109.6
C10—C11—H11	118.6	C20—C19—H19A	109.6
C12—C11—H11	118.6	C18—C19—H19B	109.6
C22—C27—O2	116.68 (15)	C20—C19—H19B	109.6
C22—C27—C26	122.35 (19)	H19A—C19—H19B	108.1
O2—C27—C26	120.94 (18)	C19—C18—C17	111.34 (18)
O5—C15—N3	123.95 (17)	C19—C18—H18A	109.4
O5—C15—C1	119.73 (16)	C17—C18—H18A	109.4
N3—C15—C1	116.14 (15)	C19—C18—H18B	109.4
O1—C2—N1	120.96 (17)	C17—C18—H18B	109.4
O1—C2—C3	122.76 (17)	H18A—C18—H18B	108.0
N1—C2—C3	116.18 (16)	C16—C17—C18	110.87 (18)
O4—N2—O3	124.5 (2)	C16—C17—H17A	109.5
O4—N2—C24	118.7 (2)	C18—C17—H17A	109.5
O3—N2—C24	116.8 (3)	C16—C17—H17B	109.5
C3—C8—C7	116.36 (18)	C18—C17—H17B	109.5
C3—C8—C9	119.33 (16)	H17A—C17—H17B	108.1
C7—C8—C9	124.15 (18)	C4—C5—C6	119.3 (2)
C24—C23—C22	118.1 (2)	C4—C5—H5	120.4
C24—C23—H23	121.0	C6—C5—H5	120.4
C22—C23—H23	121.0	C7—C6—C5	121.2 (2)
C25—C24—C23	122.5 (2)	C7—C6—H6	119.4
C25—C24—N2	119.3 (2)	C5—C6—H6	119.4
C23—C24—N2	118.2 (2)	C19—C20—C21	111.0 (2)
C25—C26—C27	118.1 (2)	C19—C20—H20A	109.4
C25—C26—H26	120.9	C21—C20—H20A	109.4
C27—C26—H26	120.9	C19—C20—H20B	109.4
C24—C25—C26	119.56 (18)	C21—C20—H20B	109.4
C24—C25—H25	120.2	H20A—C20—H20B	108.0
C26—C25—H25	120.2
C27—O2—C13—C12	129.21 (16)	N1—C1—C15—N3	161.90 (15)
C27—O2—C13—C14	−53.3 (2)	C22—C1—C15—N3	36.3 (2)
C12—C13—C14—N1	171.12 (16)	C14—N1—C2—O1	169.55 (18)
O2—C13—C14—N1	−6.2 (3)	C1—N1—C2—O1	−3.9 (3)
C12—C13—C14—C9	−7.3 (3)	C14—N1—C2—C3	−13.8 (2)
O2—C13—C14—C9	175.38 (15)	C1—N1—C2—C3	172.76 (15)
C2—N1—C14—C13	−176.13 (16)	C4—C3—C2—O1	11.5 (3)
C1—N1—C14—C13	−3.2 (2)	C8—C3—C2—O1	−172.22 (19)
C2—N1—C14—C9	2.3 (2)	C4—C3—C2—N1	−165.04 (17)
C1—N1—C14—C9	175.19 (15)	C8—C3—C2—N1	11.2 (3)
C13—C14—C9—C10	10.7 (2)	C4—C3—C8—C7	3.0 (3)
N1—C14—C9—C10	−167.78 (15)	C2—C3—C8—C7	−173.10 (18)
C13—C14—C9—C8	−169.55 (15)	C4—C3—C8—C9	178.60 (18)
N1—C14—C9—C8	12.0 (2)	C2—C3—C8—C9	2.5 (3)
C11—C10—C9—C14	−7.5 (3)	C14—C9—C8—C3	−14.1 (2)
C28—C10—C9—C14	167.06 (17)	C10—C9—C8—C3	165.58 (17)
C11—C10—C9—C8	172.82 (17)	C14—C9—C8—C7	161.12 (18)
C28—C10—C9—C8	−12.7 (3)	C10—C9—C8—C7	−19.1 (3)
O2—C13—C12—C11	177.86 (15)	C27—C22—C23—C24	−0.3 (3)
C14—C13—C12—C11	0.3 (3)	C1—C22—C23—C24	−175.65 (17)
O2—C13—C12—C29	1.1 (2)	C22—C23—C24—C25	−0.6 (3)
C14—C13—C12—C29	−176.40 (17)	C22—C23—C24—N2	179.31 (17)
C2—N1—C1—C22	−124.19 (16)	O4—N2—C24—C25	170.6 (2)
C14—N1—C1—C22	62.3 (2)	O3—N2—C24—C25	−11.2 (3)
C2—N1—C1—C15	105.92 (17)	O4—N2—C24—C23	−9.4 (3)
C14—N1—C1—C15	−67.58 (19)	O3—N2—C24—C23	168.84 (19)
C27—C22—C1—N1	−69.71 (19)	C22—C27—C26—C25	−1.8 (3)
C23—C22—C1—N1	105.78 (19)	O2—C27—C26—C25	−179.40 (17)
C27—C22—C1—C15	56.2 (2)	C23—C24—C25—C26	0.3 (3)
C23—C22—C1—C15	−128.31 (18)	N2—C24—C25—C26	−179.63 (18)
C15—N3—C16—C21	70.1 (2)	C27—C26—C25—C24	0.9 (3)
C15—N3—C16—C17	−167.00 (17)	C8—C3—C4—C5	−0.6 (3)
C9—C10—C11—C12	0.4 (3)	C2—C3—C4—C5	175.6 (2)
C28—C10—C11—C12	−174.57 (18)	N3—C16—C21—C20	−179.58 (19)
C13—C12—C11—C10	3.3 (3)	C17—C16—C21—C20	57.4 (2)
C29—C12—C11—C10	180.00 (18)	C3—C8—C7—C6	−3.3 (3)
C23—C22—C27—O2	179.20 (15)	C9—C8—C7—C6	−178.7 (2)
C1—C22—C27—O2	−5.1 (2)	C20—C19—C18—C17	−56.0 (3)
C23—C22—C27—C26	1.5 (3)	N3—C16—C17—C18	−179.81 (18)
C1—C22—C27—C26	177.21 (17)	C21—C16—C17—C18	−56.6 (2)
C13—O2—C27—C22	75.73 (19)	C19—C18—C17—C16	56.3 (3)
C13—O2—C27—C26	−106.56 (19)	C3—C4—C5—C6	−1.5 (4)
C16—N3—C15—O5	12.4 (3)	C8—C7—C6—C5	1.4 (4)
C16—N3—C15—C1	−172.54 (15)	C4—C5—C6—C7	1.1 (4)
N1—C1—C15—O5	−22.8 (2)	C18—C19—C20—C21	57.0 (3)
C22—C1—C15—O5	−148.36 (17)	C16—C21—C20—C19	−57.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3i	0.86	2.29	3.046 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3i	0.86	2.29	3.046 (2)	147

Symmetry code: (i) .