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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1996.
Published online 2009 July 25. doi:  10.1107/S1600536809028712
PMCID: PMC2977510

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

Abstract

In the title compound, C29H27N3O5, a dibenz[b,f][1,4]oxazepine derivative, the cyclo­hexane 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. Inter­molecular N—H(...)O hydrogen bonding between imino and nitro groups links two mol­ecules into a centrosymmetric dimer.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1996-scheme1.jpg

Experimental

Crystal data

  • C29H27N3O5
  • M r = 497.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1996-efi1.jpg
  • 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 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported by a research grant from the National Natural Science Foundation of China (grant No. 20672092). Professor Wei-Min Dai is thanked for his valuable suggestions. Mr Jianming Gu and Ms Xiurong Hu of the X-ray crystallography facility of Zhejiang University are acknowledged for their assistance with the crystal structural analysis.

supplementary crystallographic information

Comment

The title compound, C29H27N3O5, is viewed as the derivative of dibenz[b,f][1,4]oxazepines, which have been reported to deliver various biological activities such as non-nucleoside inhibitor of HIV-1 reverse transcriptase (Klunder et al., 1992; Merluzzi et al., 1990), antidepressant (Nagarajan et al., 1986), and PGE2 antagonist and analgesic (Hallinan et al., 1993, 1996). The title compound has recently been obtained during microwave-assisted synthesis of a derivative of dibenz[b,f][1,4]oxazepines (Dai & Shi, 2007; Xing et al., 2006) with a microwave-assisted palladium-catalyzed intramolecular direct arylation reaction (Wu et al., 2007). We report here its crystal structure.

In the molecular structure (Fig. 1) there are one cyclohexane, one oxazepine and one piperidin-2-one rings. The cyclohexane ring adopts a chair conformation with atoms C16 and C19 deviated from the mean plane formed by the other four atoms by 0.677 (3) and -0.673 (4) Å, respectively. The 7-membered oxazepine ring has a twist-boat conformation, and the piperidin-2-one assumes a flatboat conformation. Intermolecular N—H···O hydrogen-bond bonding between imino and nitro groups (Table 1) links two molecules into the centro-symmetric dimer.

Experimental

A 10-ml pressurized process vial was charged with the bromide (59.5 mg, 0.10 mmol), Pd(OAc)2 (0.6 mg, 0.0026 mmol), 1,1'-bis(diphenylphosphino)ferrocene (1.6 mg, 0.0028 mmol), and K2CO3 (27.7 mg, 0.20 mmol) and it was sealed with a cap containing a silicon septum. The vial was then evacuated and backfilled with N2 (repeated for several times) through the cap using a needle. To the degassed vial was added degassed anhydrous PhMe (2 ml) through the cap using a syringe. The loaded vial was then placed into the microwave reactor cavity and was heated at 423 K for 1 h. After cooled to room temperature the resultant mixture was filtered off through a plug of Celite with washing by EtOAc. The combined filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, 20% EtOAc in petroleum ether) to furnish the title compound in 95% yield (48.5 mg) as a pale yellow solid. m.p. > 555 K (EtOAc-hexane). Single crystals suitable for X-ray diffraction of the title compound were grown in the mixed solvent of ethyl acetate and hexane.

Refinement

All H atoms were placed in calculated positions with C—H = 0.93–0.98Å and N—H = 0.86 Å and included in the refinement in riding model, with Uiso(H) = 1.2 Ueq(C,N). The H atoms of one methyl group are equally disordered over two sites.

Figures

Fig. 1.
A view of (1). Displacement ellipsoids are drawn at 40% probability level and H atoms are shown as small circles of arbitary radii.

Crystal data

C29H27N3O5F(000) = 1048
Mr = 497.54Dx = 1.348 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15928 reflections
a = 10.7451 (4) Åθ = 3.1–27.5°
b = 27.8791 (7) ŵ = 0.09 mm1
c = 8.4917 (3) ÅT = 296 K
β = 105.428 (13)°Chunk, yellow
V = 2452.1 (2) Å30.28 × 0.26 × 0.11 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer3756 reflections with I > 2σ(I)
Radiation source: rolling anodeRint = 0.054
graphiteθmax = 27.5°, θmin = 3.1°
Detector resolution: 10.00 pixels mm-1h = −13→13
ω scansk = −36→35
23870 measured reflectionsl = −10→10
5594 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.127w = 1/[σ2(Fo2) + (0.0432P)2 + 1P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5594 reflectionsΔρmax = 0.29 e Å3
336 parametersΔρmin = −0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (10)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O20.52077 (12)0.14876 (4)0.75758 (15)0.0441 (3)
N10.30895 (13)0.12575 (5)0.46737 (17)0.0363 (3)
O50.53052 (13)0.12552 (5)0.37217 (15)0.0509 (4)
C130.43278 (17)0.18313 (6)0.6721 (2)0.0371 (4)
C140.32745 (16)0.17213 (6)0.5375 (2)0.0355 (4)
N30.63285 (14)0.07287 (6)0.56536 (19)0.0429 (4)
H30.62290.04980.62810.052*
C100.27335 (18)0.25731 (7)0.5195 (2)0.0423 (4)
C90.23969 (17)0.20945 (6)0.4689 (2)0.0383 (4)
C220.40912 (16)0.07561 (6)0.7002 (2)0.0381 (4)
O10.20934 (15)0.07613 (5)0.25999 (19)0.0654 (4)
C120.46090 (18)0.22939 (7)0.7269 (2)0.0419 (4)
C10.40183 (16)0.08658 (6)0.5246 (2)0.0364 (4)
H10.36570.05810.46150.044*
C160.76257 (17)0.08427 (6)0.5510 (2)0.0406 (4)
H160.75860.08690.43470.049*
C30.10767 (18)0.15002 (7)0.2797 (2)0.0437 (4)
C110.38132 (19)0.26588 (7)0.6456 (2)0.0453 (4)
H110.40190.29740.67790.054*
C270.46631 (17)0.10965 (7)0.8143 (2)0.0411 (4)
C150.52969 (17)0.09773 (6)0.4828 (2)0.0378 (4)
C20.21089 (18)0.11460 (7)0.3296 (2)0.0440 (4)
N20.3006 (2)−0.01158 (8)0.9665 (3)0.0698 (6)
C80.11937 (18)0.19597 (7)0.3490 (2)0.0430 (4)
C230.35448 (18)0.03542 (7)0.7497 (2)0.0455 (5)
H230.31500.01200.67490.055*
C240.3602 (2)0.03099 (8)0.9136 (3)0.0521 (5)
C260.4739 (2)0.10462 (8)0.9787 (2)0.0531 (5)
H260.51510.12761.05400.064*
O30.3241 (2)−0.01856 (7)1.1134 (2)0.0931 (7)
C250.4187 (2)0.06458 (8)1.0275 (3)0.0581 (6)
H250.42110.06041.13690.070*
C4−0.0059 (2)0.13491 (9)0.1673 (3)0.0583 (6)
H4−0.01090.10430.12230.070*
C280.2043 (2)0.30111 (7)0.4341 (3)0.0576 (5)
H28A0.12880.30710.47120.086*
H28B0.17930.29570.31830.086*
H28C0.26090.32830.45850.086*
C290.5782 (2)0.24052 (8)0.8644 (3)0.0555 (5)
H29A0.58200.27440.88560.067*0.50
H29B0.65440.23070.83450.067*0.50
H29C0.57290.22360.96080.067*0.50
H29D0.62430.21140.90170.067*0.50
H29E0.55180.25510.95280.067*0.50
H29F0.63330.26220.82650.067*0.50
C210.8092 (2)0.13172 (8)0.6321 (3)0.0585 (6)
H21A0.81130.13020.74690.070*
H21B0.74980.15700.58190.070*
C70.0090 (2)0.22515 (8)0.3054 (3)0.0586 (6)
H70.01090.25530.35290.070*
C191.0384 (2)0.10368 (9)0.6890 (3)0.0697 (7)
H19A1.12230.11110.67280.084*
H19B1.04750.10170.80550.084*
C180.9917 (2)0.05620 (8)0.6100 (3)0.0624 (6)
H18A1.05080.03110.66210.075*
H18B0.99100.05730.49560.075*
O40.2348 (2)−0.03785 (8)0.8627 (3)0.1074 (8)
C170.85656 (19)0.04450 (8)0.6240 (3)0.0560 (5)
H17A0.82750.01460.56760.067*
H17B0.85880.04030.73820.067*
C5−0.1100 (2)0.16528 (10)0.1235 (3)0.0711 (7)
H5−0.18510.15570.04700.085*
C6−0.1020 (2)0.21008 (10)0.1942 (3)0.0717 (7)
H6−0.17290.23050.16610.086*
C200.9432 (2)0.14320 (9)0.6151 (4)0.0747 (7)
H20A0.93970.14680.50040.090*
H20B0.97250.17330.66960.090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0353 (7)0.0476 (7)0.0436 (7)0.0026 (6)0.0003 (6)0.0016 (6)
N10.0318 (7)0.0418 (8)0.0331 (7)0.0010 (6)0.0050 (6)−0.0007 (6)
O50.0476 (8)0.0657 (9)0.0409 (7)0.0051 (7)0.0144 (6)0.0145 (7)
C130.0336 (9)0.0430 (9)0.0344 (9)0.0014 (7)0.0084 (7)0.0016 (7)
C140.0333 (9)0.0417 (9)0.0324 (8)−0.0011 (7)0.0104 (7)0.0008 (7)
N30.0347 (8)0.0480 (9)0.0470 (9)0.0021 (7)0.0125 (7)0.0101 (7)
C100.0417 (10)0.0443 (10)0.0441 (10)0.0042 (8)0.0169 (9)0.0052 (8)
C90.0356 (9)0.0453 (10)0.0349 (9)0.0020 (8)0.0111 (7)0.0045 (7)
C220.0305 (9)0.0470 (10)0.0362 (9)0.0065 (8)0.0075 (7)0.0064 (8)
O10.0584 (9)0.0635 (9)0.0603 (9)0.0070 (8)−0.0088 (7)−0.0223 (8)
C120.0398 (10)0.0487 (10)0.0381 (9)−0.0044 (8)0.0122 (8)−0.0032 (8)
C10.0348 (9)0.0392 (9)0.0334 (8)0.0006 (7)0.0059 (7)0.0002 (7)
C160.0346 (9)0.0459 (10)0.0425 (10)−0.0002 (8)0.0126 (8)0.0001 (8)
C30.0342 (10)0.0584 (11)0.0356 (9)0.0001 (8)0.0044 (8)0.0035 (8)
C110.0486 (11)0.0430 (10)0.0462 (10)−0.0027 (9)0.0157 (9)−0.0042 (8)
C270.0354 (9)0.0495 (10)0.0372 (9)0.0088 (8)0.0077 (8)0.0050 (8)
C150.0377 (10)0.0432 (10)0.0323 (9)−0.0003 (8)0.0088 (7)−0.0010 (7)
C20.0380 (10)0.0523 (11)0.0384 (9)−0.0018 (8)0.0047 (8)−0.0022 (8)
N20.0618 (13)0.0776 (14)0.0797 (15)0.0213 (11)0.0359 (12)0.0415 (12)
C80.0364 (10)0.0525 (11)0.0400 (10)0.0029 (8)0.0103 (8)0.0088 (8)
C230.0352 (10)0.0522 (11)0.0487 (11)0.0043 (8)0.0106 (8)0.0113 (9)
C240.0451 (11)0.0619 (13)0.0548 (12)0.0168 (10)0.0229 (10)0.0215 (10)
C260.0589 (13)0.0615 (13)0.0362 (10)0.0213 (11)0.0078 (9)0.0017 (9)
O30.1025 (15)0.1061 (15)0.0891 (13)0.0394 (12)0.0579 (12)0.0579 (11)
C250.0669 (14)0.0724 (14)0.0402 (11)0.0292 (12)0.0234 (10)0.0174 (10)
C40.0450 (12)0.0729 (14)0.0485 (11)−0.0028 (11)−0.0022 (9)−0.0050 (10)
C280.0593 (13)0.0470 (11)0.0654 (13)0.0083 (10)0.0145 (11)0.0086 (10)
C290.0500 (12)0.0595 (12)0.0526 (12)−0.0089 (10)0.0061 (10)−0.0104 (10)
C210.0457 (12)0.0549 (12)0.0732 (14)0.0015 (10)0.0132 (11)−0.0130 (11)
C70.0457 (12)0.0596 (13)0.0654 (14)0.0090 (10)0.0059 (11)0.0089 (11)
C190.0393 (12)0.0793 (16)0.0898 (17)−0.0087 (11)0.0158 (12)−0.0193 (14)
C180.0400 (11)0.0662 (14)0.0813 (16)0.0054 (10)0.0168 (11)−0.0123 (12)
O40.1032 (17)0.1027 (16)0.1141 (18)−0.0339 (14)0.0253 (14)0.0357 (14)
C170.0417 (11)0.0503 (12)0.0751 (15)0.0034 (9)0.0140 (10)0.0007 (10)
C50.0402 (12)0.0983 (19)0.0620 (14)0.0048 (12)−0.0087 (11)0.0015 (14)
C60.0434 (13)0.0856 (18)0.0755 (16)0.0171 (12)−0.0030 (12)0.0097 (14)
C200.0544 (14)0.0601 (14)0.108 (2)−0.0151 (11)0.0187 (14)−0.0168 (14)

Geometric parameters (Å, °)

O2—C271.383 (2)C23—C241.382 (3)
O2—C131.405 (2)C23—H230.9300
N1—C21.386 (2)C24—C251.373 (3)
N1—C141.415 (2)C26—C251.379 (3)
N1—C11.472 (2)C26—H260.9300
O5—C151.219 (2)C25—H250.9300
C13—C121.377 (2)C4—C51.373 (3)
C13—C141.412 (2)C4—H40.9300
C14—C91.421 (2)C28—H28A0.9600
N3—C151.337 (2)C28—H28B0.9600
N3—C161.466 (2)C28—H28C0.9600
N3—H30.8600C29—H29A0.9600
C10—C111.374 (3)C29—H29B0.9600
C10—C91.419 (3)C29—H29C0.9600
C10—C281.510 (3)C29—H29D0.9600
C9—C81.466 (3)C29—H29E0.9600
C22—C271.378 (3)C29—H29F0.9600
C22—C231.381 (3)C21—C201.519 (3)
C22—C11.503 (2)C21—H21A0.9700
O1—C21.223 (2)C21—H21B0.9700
C12—C111.389 (3)C7—C61.375 (3)
C12—C291.505 (3)C7—H70.9300
C1—C151.540 (2)C19—C181.508 (3)
C1—H10.9800C19—C201.521 (4)
C16—C211.514 (3)C19—H19A0.9700
C16—C171.517 (3)C19—H19B0.9700
C16—H160.9800C18—C171.524 (3)
C3—C41.400 (3)C18—H18A0.9700
C3—C81.401 (3)C18—H18B0.9700
C3—C21.461 (3)C17—H17A0.9700
C11—H110.9300C17—H17B0.9700
C27—C261.384 (3)C5—C61.378 (4)
N2—O41.217 (3)C5—H50.9300
N2—O31.221 (3)C6—H60.9300
N2—C241.474 (3)C20—H20A0.9700
C8—C71.404 (3)C20—H20B0.9700
C27—O2—C13115.38 (13)C5—C4—C3119.9 (2)
C2—N1—C14123.40 (15)C5—C4—H4120.0
C2—N1—C1114.14 (14)C3—C4—H4120.0
C14—N1—C1122.12 (13)C10—C28—H28A109.5
C12—C13—O2114.03 (15)C10—C28—H28B109.5
C12—C13—C14122.24 (16)H28A—C28—H28B109.5
O2—C13—C14123.68 (15)C10—C28—H28C109.5
C13—C14—N1122.13 (15)H28A—C28—H28C109.5
C13—C14—C9118.32 (16)H28B—C28—H28C109.5
N1—C14—C9119.54 (15)C12—C29—H29A109.5
C15—N3—C16121.20 (15)C12—C29—H29B109.5
C15—N3—H3119.4H29A—C29—H29B109.5
C16—N3—H3119.4C12—C29—H29C109.5
C11—C10—C9119.59 (17)H29A—C29—H29C109.5
C11—C10—C28116.01 (18)H29B—C29—H29C109.5
C9—C10—C28124.19 (18)C12—C29—H29D109.5
C14—C9—C10118.47 (16)H29A—C29—H29D141.1
C14—C9—C8117.61 (16)H29B—C29—H29D56.3
C10—C9—C8123.91 (16)H29C—C29—H29D56.3
C27—C22—C23119.37 (17)C12—C29—H29E109.5
C27—C22—C1116.93 (16)H29A—C29—H29E56.3
C23—C22—C1123.55 (17)H29B—C29—H29E141.1
C13—C12—C11117.88 (17)H29C—C29—H29E56.3
C13—C12—C29121.21 (17)H29D—C29—H29E109.5
C11—C12—C29120.83 (17)C12—C29—H29F109.5
N1—C1—C22109.29 (14)H29A—C29—H29F56.3
N1—C1—C15110.02 (14)H29B—C29—H29F56.3
C22—C1—C15117.11 (14)H29C—C29—H29F141.1
N1—C1—H1106.6H29D—C29—H29F109.5
C22—C1—H1106.6H29E—C29—H29F109.5
C15—C1—H1106.6C16—C21—C20110.38 (18)
N3—C16—C21110.99 (15)C16—C21—H21A109.6
N3—C16—C17110.60 (15)C20—C21—H21A109.6
C21—C16—C17110.42 (17)C16—C21—H21B109.6
N3—C16—H16108.2C20—C21—H21B109.6
C21—C16—H16108.2H21A—C21—H21B108.1
C17—C16—H16108.2C6—C7—C8121.4 (2)
C4—C3—C8121.73 (18)C6—C7—H7119.3
C4—C3—C2116.84 (18)C8—C7—H7119.3
C8—C3—C2121.33 (16)C18—C19—C20110.2 (2)
C10—C11—C12122.71 (18)C18—C19—H19A109.6
C10—C11—H11118.6C20—C19—H19A109.6
C12—C11—H11118.6C18—C19—H19B109.6
C22—C27—O2116.68 (15)C20—C19—H19B109.6
C22—C27—C26122.35 (19)H19A—C19—H19B108.1
O2—C27—C26120.94 (18)C19—C18—C17111.34 (18)
O5—C15—N3123.95 (17)C19—C18—H18A109.4
O5—C15—C1119.73 (16)C17—C18—H18A109.4
N3—C15—C1116.14 (15)C19—C18—H18B109.4
O1—C2—N1120.96 (17)C17—C18—H18B109.4
O1—C2—C3122.76 (17)H18A—C18—H18B108.0
N1—C2—C3116.18 (16)C16—C17—C18110.87 (18)
O4—N2—O3124.5 (2)C16—C17—H17A109.5
O4—N2—C24118.7 (2)C18—C17—H17A109.5
O3—N2—C24116.8 (3)C16—C17—H17B109.5
C3—C8—C7116.36 (18)C18—C17—H17B109.5
C3—C8—C9119.33 (16)H17A—C17—H17B108.1
C7—C8—C9124.15 (18)C4—C5—C6119.3 (2)
C24—C23—C22118.1 (2)C4—C5—H5120.4
C24—C23—H23121.0C6—C5—H5120.4
C22—C23—H23121.0C7—C6—C5121.2 (2)
C25—C24—C23122.5 (2)C7—C6—H6119.4
C25—C24—N2119.3 (2)C5—C6—H6119.4
C23—C24—N2118.2 (2)C19—C20—C21111.0 (2)
C25—C26—C27118.1 (2)C19—C20—H20A109.4
C25—C26—H26120.9C21—C20—H20A109.4
C27—C26—H26120.9C19—C20—H20B109.4
C24—C25—C26119.56 (18)C21—C20—H20B109.4
C24—C25—H25120.2H20A—C20—H20B108.0
C26—C25—H25120.2
C27—O2—C13—C12129.21 (16)N1—C1—C15—N3161.90 (15)
C27—O2—C13—C14−53.3 (2)C22—C1—C15—N336.3 (2)
C12—C13—C14—N1171.12 (16)C14—N1—C2—O1169.55 (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—C9175.38 (15)C1—N1—C2—C3172.76 (15)
C2—N1—C14—C13−176.13 (16)C4—C3—C2—O111.5 (3)
C1—N1—C14—C13−3.2 (2)C8—C3—C2—O1−172.22 (19)
C2—N1—C14—C92.3 (2)C4—C3—C2—N1−165.04 (17)
C1—N1—C14—C9175.19 (15)C8—C3—C2—N111.2 (3)
C13—C14—C9—C1010.7 (2)C4—C3—C8—C73.0 (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—C9178.60 (18)
N1—C14—C9—C812.0 (2)C2—C3—C8—C92.5 (3)
C11—C10—C9—C14−7.5 (3)C14—C9—C8—C3−14.1 (2)
C28—C10—C9—C14167.06 (17)C10—C9—C8—C3165.58 (17)
C11—C10—C9—C8172.82 (17)C14—C9—C8—C7161.12 (18)
C28—C10—C9—C8−12.7 (3)C10—C9—C8—C7−19.1 (3)
O2—C13—C12—C11177.86 (15)C27—C22—C23—C24−0.3 (3)
C14—C13—C12—C110.3 (3)C1—C22—C23—C24−175.65 (17)
O2—C13—C12—C291.1 (2)C22—C23—C24—C25−0.6 (3)
C14—C13—C12—C29−176.40 (17)C22—C23—C24—N2179.31 (17)
C2—N1—C1—C22−124.19 (16)O4—N2—C24—C25170.6 (2)
C14—N1—C1—C2262.3 (2)O3—N2—C24—C25−11.2 (3)
C2—N1—C1—C15105.92 (17)O4—N2—C24—C23−9.4 (3)
C14—N1—C1—C15−67.58 (19)O3—N2—C24—C23168.84 (19)
C27—C22—C1—N1−69.71 (19)C22—C27—C26—C25−1.8 (3)
C23—C22—C1—N1105.78 (19)O2—C27—C26—C25−179.40 (17)
C27—C22—C1—C1556.2 (2)C23—C24—C25—C260.3 (3)
C23—C22—C1—C15−128.31 (18)N2—C24—C25—C26−179.63 (18)
C15—N3—C16—C2170.1 (2)C27—C26—C25—C240.9 (3)
C15—N3—C16—C17−167.00 (17)C8—C3—C4—C5−0.6 (3)
C9—C10—C11—C120.4 (3)C2—C3—C4—C5175.6 (2)
C28—C10—C11—C12−174.57 (18)N3—C16—C21—C20−179.58 (19)
C13—C12—C11—C103.3 (3)C17—C16—C21—C2057.4 (2)
C29—C12—C11—C10180.00 (18)C3—C8—C7—C6−3.3 (3)
C23—C22—C27—O2179.20 (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—C261.5 (3)N3—C16—C17—C18−179.81 (18)
C1—C22—C27—C26177.21 (17)C21—C16—C17—C18−56.6 (2)
C13—O2—C27—C2275.73 (19)C19—C18—C17—C1656.3 (3)
C13—O2—C27—C26−106.56 (19)C3—C4—C5—C6−1.5 (4)
C16—N3—C15—O512.4 (3)C8—C7—C6—C51.4 (4)
C16—N3—C15—C1−172.54 (15)C4—C5—C6—C71.1 (4)
N1—C1—C15—O5−22.8 (2)C18—C19—C20—C2157.0 (3)
C22—C1—C15—O5−148.36 (17)C16—C21—C20—C19−57.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O3i0.862.293.046 (2)147

Symmetry codes: (i) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2558).

References

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