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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2178.
Published online 2008 October 25. doi:  10.1107/S1600536808034247
PMCID: PMC2959758

N-{N-[N-(1,1-Dimethyl­ethoxy­carbon­yl)-l-leuc­yl]-N-methyl-l-leuc­yl}-N-methyl-l-leucine benzyl ester

Abstract

The tripeptide title compound, C32H53N3O6, synthesized in 80% yield by coupling of N-methyl-l-leucine benzyl ester with tert-butoxy­carbonyl-l-leucyl-N-methyl-l-leucine at 273 K, conjugates through two amide linkages and includes two protecting groups: a tert-butyl­oxycarbonyl group at the C-tip and a benzyl group at the N-tip. A classical inter­molecular N—H(...)O hydrogen bond and a weak non-conventional inter­molecular C—H(...)O contact connect the mol­ecules, forming layers parallel to (001).

Related literature

For the structure of a related dipeptide, see: Liao et al. (2007 [triangle]). For the synthesis of linear peptide fragments of cyclic penta­peptide, see: Xu et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2178-scheme1.jpg

Experimental

Crystal data

  • C32H53N3O6
  • M r = 575.77
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-64-o2178-efi1.jpg
  • a = 13.9784 (3) Å
  • c = 30.4763 (15) Å
  • V = 5157.1 (3) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 (2) K
  • 0.47 × 0.42 × 0.26 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.965, T max = 0.981
  • 27507 measured reflections
  • 4232 independent reflections
  • 3541 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.138
  • S = 1.05
  • 4232 reflections
  • 381 parameters
  • 18 restraints
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034247/si2119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034247/si2119Isup2.hkl

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

Acknowledgments

This work was supported by grants from the National High Technology Development Project (863 Project) (Nos. 2006A A09Z408 GDSFC 06025194, 2005 A30503001, and 2006Z3-E4041), and the National Natural Science Fund (No. 20772048).

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) was prepared from the dipeptide Benzyl-2-{[2-(tert-butoxycarbonylamino)-4-methylpentanoyl]methylamino} -4-methylpentanoate, which is an intermediate product in the synthesis of polypeptides (Xu et al., 2008). The bond lengths and angles of (I) are unexceptional and are in good agreement with the corresponding values in the dipeptide structure (Liao et al., 2007). A classic intermolecular N—H···O hydrogen bond (Table 1) and a weak non-conventional C—H···O contact connect the molecules to form layers parallel to (0 0 1).

Experimental

The benzyl in Benzyl-2-{[2-(tert-butoxycarbonylamino)-4-methylpentanoyl] methylamino}-4-methylpentanoate (2 mmol) was removed, dried and dissolved using THF under an atmosphere of nitrogen. A coupling reagent 3-(diethoxy-phosphoryloxy)-3H-benzo[d][1,2,3] triazin-4-one (DEPBT 3 mmol) and diisopropylethylamine (DIPEA) were added successively at 273 K. After 10 min, the amine (2.4 mmol) was added in one portion. The mixture was allowed to stand at room temperature for 12 h. The reactions were monitored using TLC. The reaction was concentrated and it was not necessary to carry out the postproccessing, the material was directly subjected to silica gel column chromatography using n-hexane/acetone (20:1) isocratic elution to give the title compound. Colorless crystals suitable for X-ray analysis grew over a period of a week when the solution was exposed to air.

Refinement

Hydrogen atoms attached to C or N atoms were located at geometrically calculated positions [1.00 Å (CH), 0.99 Å (CH2), 0.98 Å (CH3), and 0.88 Å (NH)] and refined with isotropic thermal parameters Uiso(H) equal to 1.2 for CH, CH2 and NH, and 1.5 for CH3Ueq(C atoms).

In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C32H53N3O6Dx = 1.112 Mg m3
Mr = 575.77Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3121Cell parameters from 5764 reflections
Hall symbol: P 31 2"θ = 2.2–26.7°
a = 13.9784 (3) ŵ = 0.08 mm1
c = 30.4763 (15) ÅT = 173 K
V = 5157.1 (3) Å3Block, colorless
Z = 60.47 × 0.42 × 0.26 mm
F(000) = 1884

Data collection

Bruker SMART 1000 CCD diffractometer4232 independent reflections
Radiation source: fine-focus sealed tube3541 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −17→13
Tmin = 0.965, Tmax = 0.981k = −17→17
27507 measured reflectionsl = −39→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.076P)2 + 1.5629P] where P = (Fo2 + 2Fc2)/3
4232 reflections(Δ/σ)max < 0.001
381 parametersΔρmax = 0.43 e Å3
18 restraintsΔρmin = −0.23 e Å3

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*/Ueq
C10.2754 (3)0.1859 (3)0.23021 (11)0.0520 (8)
H10.35380.22380.23180.062*
C20.2238 (4)0.2413 (3)0.21488 (13)0.0598 (10)
H20.26660.31650.20640.072*
C30.1141 (4)0.1899 (4)0.2119 (2)0.0928 (17)
H30.07840.22760.20100.111*
C40.0541 (4)0.0827 (5)0.2248 (3)0.130 (3)
H4−0.02420.04610.22340.156*
C50.1050 (4)0.0259 (4)0.2399 (2)0.1001 (19)
H50.0617−0.04960.24800.120*
C60.2170 (3)0.0782 (3)0.24319 (12)0.0505 (8)
C70.2703 (3)0.0129 (3)0.25971 (12)0.0519 (8)
H7A0.2490−0.00990.29060.062*
H7B0.2463−0.05420.24160.062*
C80.4532 (3)0.0463 (3)0.26799 (10)0.0437 (7)
C90.5736 (3)0.1334 (2)0.26120 (9)0.0360 (6)
H90.59240.12640.23010.043*
C100.6515 (3)0.1151 (3)0.29028 (10)0.0457 (8)
H10A0.62640.03520.29100.055*
H10B0.64740.13840.32060.055*
C110.7710 (3)0.1778 (3)0.27493 (11)0.0511 (8)
H110.78800.25330.26560.061*
C120.8493 (4)0.1908 (5)0.31243 (15)0.0809 (14)
H12A0.83320.11770.32250.121*
H12B0.83920.23080.33670.121*
H12C0.92590.23230.30200.121*
C130.7895 (4)0.1226 (5)0.23608 (13)0.0694 (12)
H13A0.77610.04930.24470.104*
H13B0.86580.16750.22580.104*
H13C0.73850.11490.21240.104*
C140.5605 (3)0.2723 (3)0.30884 (9)0.0432 (7)
H14A0.62780.32800.32360.065*
H14B0.52410.20560.32700.065*
H14C0.51040.30150.30450.065*
C150.6162 (2)0.3192 (2)0.23346 (9)0.0321 (6)
C160.6491 (2)0.2951 (2)0.18839 (8)0.0298 (5)
H160.68440.24880.19290.036*
C170.7328 (2)0.4028 (2)0.16595 (9)0.0379 (6)
H17A0.69770.44810.16030.045*
H17B0.79610.44490.18590.045*
C180.7752 (3)0.3829 (3)0.12259 (10)0.0412 (7)
H180.71000.32500.10610.049*
C190.8540 (4)0.3405 (4)0.12951 (13)0.0650 (10)
H19A0.87680.32620.10100.097*
H19B0.81740.27190.14650.097*
H19C0.91910.39580.14550.097*
C200.8274 (4)0.4870 (4)0.09480 (13)0.0723 (13)
H20A0.89210.54520.11000.108*
H20B0.77360.51140.08990.108*
H20C0.85020.47160.06650.108*
C210.4911 (3)0.2895 (3)0.14652 (9)0.0365 (6)
H21A0.51400.31690.11660.055*
H21B0.50890.35170.16620.055*
H21C0.41130.23780.14710.055*
C220.5311 (2)0.1349 (2)0.14422 (8)0.0296 (5)
C230.4365 (2)0.0770 (2)0.11090 (8)0.0294 (5)
H230.42200.13310.09680.035*
C240.3335 (2)−0.0066 (2)0.13576 (9)0.0317 (6)
H24A0.31930.03250.15970.038*
H24B0.3488−0.06180.14940.038*
C250.2289 (2)−0.0677 (3)0.10791 (9)0.0378 (6)
H250.2416−0.11160.08510.045*
C260.1327 (3)−0.1472 (3)0.13673 (11)0.0447 (7)
H26A0.1177−0.10540.15870.067*
H26B0.1517−0.19780.15150.067*
H26C0.0670−0.18970.11850.067*
C270.2013 (3)0.0120 (4)0.08478 (14)0.0685 (12)
H27A0.1348−0.02990.06690.103*
H27B0.26320.06160.06590.103*
H27C0.18820.05550.10670.103*
C280.5515 (2)0.0915 (2)0.05042 (8)0.0335 (6)
C290.6809 (3)0.0907 (3)−0.00321 (9)0.0383 (6)
C300.7820 (3)0.1894 (3)0.01674 (10)0.0512 (8)
H30A0.76530.24830.02290.077*
H30B0.84390.2164−0.00390.077*
H30C0.80200.16680.04410.077*
C310.7080 (3)0.0009 (3)−0.01504 (10)0.0463 (8)
H31A0.7347−0.01940.01110.069*
H31B0.76530.0285−0.03770.069*
H31C0.6414−0.0641−0.02610.069*
C320.6356 (3)0.1225 (3)−0.04226 (10)0.0460 (7)
H32A0.56780.0576−0.05260.069*
H32B0.69050.1501−0.06590.069*
H32C0.61920.1803−0.03360.069*
N10.5894 (2)0.24496 (19)0.26592 (7)0.0338 (5)
N20.54989 (18)0.23237 (18)0.16121 (7)0.0288 (5)
N30.46804 (19)0.02448 (19)0.07749 (7)0.0302 (5)
H3A0.4344−0.04790.07490.036*
O10.38691 (19)0.08380 (19)0.25637 (8)0.0500 (6)
O20.4211 (3)−0.0461 (2)0.27986 (13)0.0891 (11)
O30.61650 (19)0.40624 (17)0.23920 (6)0.0398 (5)
O40.58401 (17)0.09059 (17)0.15495 (7)0.0391 (5)
O50.5840 (2)0.18927 (17)0.04605 (7)0.0438 (5)
O60.59298 (17)0.03485 (17)0.02975 (6)0.0362 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0459 (19)0.056 (2)0.0467 (17)0.0203 (18)0.0047 (15)0.0046 (15)
C20.059 (2)0.052 (2)0.067 (2)0.0271 (19)−0.0005 (19)−0.0033 (18)
C30.054 (3)0.055 (3)0.167 (5)0.027 (2)−0.005 (3)0.003 (3)
C40.048 (3)0.078 (4)0.262 (8)0.029 (3)0.006 (4)0.030 (4)
C50.042 (2)0.051 (3)0.198 (6)0.016 (2)0.014 (3)0.022 (3)
C60.0374 (17)0.0439 (19)0.0607 (19)0.0131 (15)0.0018 (15)−0.0149 (15)
C70.0398 (18)0.0465 (19)0.0574 (19)0.0124 (16)0.0059 (15)0.0048 (16)
C80.0471 (18)0.0354 (16)0.0453 (16)0.0181 (14)−0.0030 (14)0.0052 (13)
C90.0430 (16)0.0338 (15)0.0351 (14)0.0221 (13)0.0023 (12)0.0029 (11)
C100.0532 (19)0.0512 (19)0.0404 (15)0.0319 (16)−0.0035 (14)0.0060 (14)
C110.049 (2)0.058 (2)0.0544 (18)0.0330 (18)−0.0101 (15)−0.0005 (16)
C120.069 (3)0.102 (4)0.082 (3)0.051 (3)−0.031 (2)−0.016 (3)
C130.064 (3)0.108 (4)0.061 (2)0.061 (3)−0.001 (2)−0.001 (2)
C140.0485 (18)0.0439 (17)0.0366 (14)0.0227 (15)0.0067 (13)−0.0019 (13)
C150.0271 (13)0.0327 (14)0.0364 (13)0.0149 (11)−0.0039 (11)−0.0024 (11)
C160.0283 (13)0.0271 (13)0.0323 (12)0.0124 (11)−0.0015 (10)−0.0013 (10)
C170.0357 (15)0.0317 (15)0.0385 (14)0.0110 (13)0.0037 (12)−0.0009 (11)
C180.0357 (16)0.0377 (16)0.0386 (14)0.0097 (13)0.0046 (12)−0.0005 (12)
C190.057 (2)0.085 (3)0.061 (2)0.042 (2)0.0086 (18)−0.004 (2)
C200.082 (3)0.062 (3)0.063 (2)0.028 (2)0.032 (2)0.018 (2)
C210.0406 (16)0.0354 (15)0.0416 (14)0.0251 (13)−0.0056 (12)−0.0046 (12)
C220.0279 (13)0.0303 (13)0.0304 (12)0.0144 (11)0.0036 (10)0.0015 (10)
C230.0293 (13)0.0294 (13)0.0310 (12)0.0157 (11)0.0008 (10)−0.0012 (10)
C240.0293 (13)0.0333 (14)0.0311 (12)0.0146 (12)0.0032 (10)−0.0004 (11)
C250.0286 (14)0.0444 (17)0.0366 (14)0.0154 (13)0.0020 (11)−0.0058 (12)
C260.0306 (15)0.0423 (17)0.0557 (17)0.0141 (14)0.0047 (13)0.0026 (14)
C270.0367 (18)0.080 (3)0.075 (2)0.0188 (19)−0.0063 (18)0.031 (2)
C280.0342 (14)0.0344 (15)0.0306 (12)0.0162 (12)0.0005 (11)−0.0011 (11)
C290.0335 (15)0.0444 (17)0.0325 (13)0.0161 (13)0.0068 (11)0.0034 (12)
C300.0382 (17)0.058 (2)0.0446 (16)0.0149 (16)0.0044 (14)−0.0013 (15)
C310.0451 (18)0.063 (2)0.0389 (15)0.0335 (17)0.0094 (14)0.0024 (15)
C320.0512 (19)0.053 (2)0.0362 (15)0.0282 (17)0.0038 (14)0.0045 (14)
N10.0375 (13)0.0324 (12)0.0321 (11)0.0179 (11)0.0019 (10)0.0012 (9)
N20.0291 (11)0.0259 (11)0.0325 (10)0.0146 (9)−0.0017 (9)−0.0004 (9)
N30.0294 (11)0.0267 (11)0.0313 (10)0.0115 (10)0.0029 (9)−0.0022 (9)
O10.0342 (12)0.0387 (13)0.0714 (15)0.0139 (10)0.0029 (11)0.0066 (11)
O20.0613 (19)0.0446 (16)0.145 (3)0.0144 (14)−0.0121 (19)0.0392 (18)
O30.0495 (13)0.0329 (10)0.0424 (10)0.0247 (10)0.0024 (9)−0.0012 (8)
O40.0400 (12)0.0364 (11)0.0479 (11)0.0242 (10)−0.0094 (9)−0.0083 (9)
O50.0502 (13)0.0315 (11)0.0461 (11)0.0176 (10)0.0135 (10)0.0055 (9)
O60.0374 (11)0.0361 (11)0.0362 (9)0.0191 (9)0.0109 (8)0.0039 (8)

Geometric parameters (Å, °)

C1—C61.364 (5)C18—C201.518 (5)
C1—C21.377 (6)C18—H181.0000
C1—H10.9500C19—H19A0.9800
C2—C31.331 (6)C19—H19B0.9800
C2—H20.9500C19—H19C0.9800
C3—C41.359 (8)C20—H20A0.9800
C3—H30.9500C20—H20B0.9800
C4—C51.382 (8)C20—H20C0.9800
C4—H40.9500C21—N21.473 (3)
C5—C61.362 (6)C21—H21A0.9800
C5—H50.9500C21—H21B0.9800
C6—C71.524 (5)C21—H21C0.9800
C7—O11.426 (4)C22—O41.223 (3)
C7—H7A0.9900C22—N21.355 (3)
C7—H7B0.9900C22—C231.537 (4)
C8—O21.193 (4)C23—N31.447 (3)
C8—O11.320 (4)C23—C241.526 (4)
C8—C91.520 (5)C23—H231.0000
C9—N11.468 (4)C24—C251.530 (4)
C9—C101.522 (4)C24—H24A0.9900
C9—H91.0000C24—H24B0.9900
C10—C111.522 (5)C25—C271.521 (5)
C10—H10A0.9900C25—C261.523 (4)
C10—H10B0.9900C25—H251.0000
C11—C131.505 (5)C26—H26A0.9800
C11—C121.529 (5)C26—H26B0.9800
C11—H111.0000C26—H26C0.9800
C12—H12A0.9800C27—H27A0.9800
C12—H12B0.9800C27—H27B0.9800
C12—H12C0.9800C27—H27C0.9800
C13—H13A0.9800C28—O51.213 (4)
C13—H13B0.9800C28—O61.349 (3)
C13—H13C0.9800C28—N31.351 (4)
C14—N11.475 (4)C29—O61.473 (3)
C14—H14A0.9800C29—C321.516 (4)
C14—H14B0.9800C29—C301.523 (5)
C14—H14C0.9800C29—C311.525 (5)
C15—O31.227 (3)C30—H30A0.9800
C15—N11.344 (4)C30—H30B0.9800
C15—C161.538 (4)C30—H30C0.9800
C16—N21.470 (3)C31—H31A0.9800
C16—C171.530 (4)C31—H31B0.9800
C16—H161.0000C31—H31C0.9800
C17—C181.529 (4)C32—H32A0.9800
C17—H17A0.9900C32—H32B0.9800
C17—H17B0.9900C32—H32C0.9800
C18—C191.504 (5)N3—H3A0.8800
C6—C1—C2121.7 (4)C18—C19—H19C109.5
C6—C1—H1119.1H19A—C19—H19C109.5
C2—C1—H1119.1H19B—C19—H19C109.5
C3—C2—C1120.4 (4)C18—C20—H20A109.5
C3—C2—H2119.8C18—C20—H20B109.5
C1—C2—H2119.8H20A—C20—H20B109.5
C2—C3—C4119.0 (5)C18—C20—H20C109.5
C2—C3—H3120.5H20A—C20—H20C109.5
C4—C3—H3120.5H20B—C20—H20C109.5
C3—C4—C5121.2 (5)N2—C21—H21A109.5
C3—C4—H4119.4N2—C21—H21B109.5
C5—C4—H4119.4H21A—C21—H21B109.5
C6—C5—C4120.0 (4)N2—C21—H21C109.5
C6—C5—H5120.0H21A—C21—H21C109.5
C4—C5—H5120.0H21B—C21—H21C109.5
C5—C6—C1117.7 (4)O4—C22—N2123.0 (2)
C5—C6—C7118.6 (4)O4—C22—C23119.2 (2)
C1—C6—C7123.7 (3)N2—C22—C23117.7 (2)
O1—C7—C6106.9 (3)N3—C23—C24111.8 (2)
O1—C7—H7A110.3N3—C23—C22109.4 (2)
C6—C7—H7A110.3C24—C23—C22108.0 (2)
O1—C7—H7B110.3N3—C23—H23109.2
C6—C7—H7B110.3C24—C23—H23109.2
H7A—C7—H7B108.6C22—C23—H23109.2
O2—C8—O1123.6 (3)C23—C24—C25115.1 (2)
O2—C8—C9125.1 (3)C23—C24—H24A108.5
O1—C8—C9111.2 (3)C25—C24—H24A108.5
N1—C9—C8110.8 (3)C23—C24—H24B108.5
N1—C9—C10112.4 (3)C25—C24—H24B108.5
C8—C9—C10112.6 (2)H24A—C24—H24B107.5
N1—C9—H9106.9C27—C25—C26110.4 (3)
C8—C9—H9106.9C27—C25—C24111.7 (3)
C10—C9—H9106.9C26—C25—C24109.6 (2)
C9—C10—C11113.3 (3)C27—C25—H25108.3
C9—C10—H10A108.9C26—C25—H25108.3
C11—C10—H10A108.9C24—C25—H25108.3
C9—C10—H10B108.9C25—C26—H26A109.5
C11—C10—H10B108.9C25—C26—H26B109.5
H10A—C10—H10B107.7H26A—C26—H26B109.5
C13—C11—C10111.5 (3)C25—C26—H26C109.5
C13—C11—C12110.7 (3)H26A—C26—H26C109.5
C10—C11—C12110.7 (3)H26B—C26—H26C109.5
C13—C11—H11107.9C25—C27—H27A109.5
C10—C11—H11107.9C25—C27—H27B109.5
C12—C11—H11107.9H27A—C27—H27B109.5
C11—C12—H12A109.5C25—C27—H27C109.5
C11—C12—H12B109.5H27A—C27—H27C109.5
H12A—C12—H12B109.5H27B—C27—H27C109.5
C11—C12—H12C109.5O5—C28—O6125.5 (3)
H12A—C12—H12C109.5O5—C28—N3123.8 (3)
H12B—C12—H12C109.5O6—C28—N3110.7 (2)
C11—C13—H13A109.5O6—C29—C32109.3 (2)
C11—C13—H13B109.5O6—C29—C30111.0 (2)
H13A—C13—H13B109.5C32—C29—C30112.5 (3)
C11—C13—H13C109.5O6—C29—C31102.1 (2)
H13A—C13—H13C109.5C32—C29—C31111.6 (3)
H13B—C13—H13C109.5C30—C29—C31109.9 (3)
N1—C14—H14A109.5C29—C30—H30A109.5
N1—C14—H14B109.5C29—C30—H30B109.5
H14A—C14—H14B109.5H30A—C30—H30B109.5
N1—C14—H14C109.5C29—C30—H30C109.5
H14A—C14—H14C109.5H30A—C30—H30C109.5
H14B—C14—H14C109.5H30B—C30—H30C109.5
O3—C15—N1121.4 (3)C29—C31—H31A109.5
O3—C15—C16119.4 (2)C29—C31—H31B109.5
N1—C15—C16119.1 (2)H31A—C31—H31B109.5
N2—C16—C17111.3 (2)C29—C31—H31C109.5
N2—C16—C15109.7 (2)H31A—C31—H31C109.5
C17—C16—C15110.4 (2)H31B—C31—H31C109.5
N2—C16—H16108.4C29—C32—H32A109.5
C17—C16—H16108.4C29—C32—H32B109.5
C15—C16—H16108.4H32A—C32—H32B109.5
C18—C17—C16112.5 (2)C29—C32—H32C109.5
C18—C17—H17A109.1H32A—C32—H32C109.5
C16—C17—H17A109.1H32B—C32—H32C109.5
C18—C17—H17B109.1C15—N1—C9125.7 (2)
C16—C17—H17B109.1C15—N1—C14117.4 (2)
H17A—C17—H17B107.8C9—N1—C14116.5 (2)
C19—C18—C20111.1 (3)C22—N2—C16117.8 (2)
C19—C18—C17112.1 (3)C22—N2—C21123.3 (2)
C20—C18—C17110.6 (3)C16—N2—C21117.6 (2)
C19—C18—H18107.6C28—N3—C23117.0 (2)
C20—C18—H18107.6C28—N3—H3A121.5
C17—C18—H18107.6C23—N3—H3A121.5
C18—C19—H19A109.5C8—O1—C7119.3 (3)
C18—C19—H19B109.5C28—O6—C29119.8 (2)
H19A—C19—H19B109.5
C6—C1—C2—C3−0.7 (7)C22—C23—C24—C25176.7 (2)
C1—C2—C3—C40.8 (9)C23—C24—C25—C27−56.8 (4)
C2—C3—C4—C5−1.4 (12)C23—C24—C25—C26−179.5 (2)
C3—C4—C5—C61.7 (13)O3—C15—N1—C9172.2 (3)
C4—C5—C6—C1−1.5 (9)C16—C15—N1—C9−8.8 (4)
C4—C5—C6—C7−179.6 (6)O3—C15—N1—C14−0.1 (4)
C2—C1—C6—C51.0 (6)C16—C15—N1—C14178.8 (2)
C2—C1—C6—C7179.0 (3)C8—C9—N1—C15−111.7 (3)
C5—C6—C7—O1175.1 (4)C10—C9—N1—C15121.2 (3)
C1—C6—C7—O1−2.9 (5)C8—C9—N1—C1460.7 (3)
O2—C8—C9—N1−154.8 (4)C10—C9—N1—C14−66.3 (3)
O1—C8—C9—N129.2 (4)O4—C22—N2—C169.8 (4)
O2—C8—C9—C10−27.9 (5)C23—C22—N2—C16−172.0 (2)
O1—C8—C9—C10156.1 (3)O4—C22—N2—C21176.2 (3)
N1—C9—C10—C11−71.4 (3)C23—C22—N2—C21−5.5 (4)
C8—C9—C10—C11162.6 (3)C17—C16—N2—C22112.7 (3)
C9—C10—C11—C13−76.7 (4)C15—C16—N2—C22−124.8 (2)
C9—C10—C11—C12159.6 (3)C17—C16—N2—C21−54.5 (3)
O3—C15—C16—N2−92.8 (3)C15—C16—N2—C2168.0 (3)
N1—C15—C16—N288.2 (3)O5—C28—N3—C23−16.8 (4)
O3—C15—C16—C1730.3 (4)O6—C28—N3—C23162.6 (2)
N1—C15—C16—C17−148.7 (3)C24—C23—N3—C28173.5 (2)
N2—C16—C17—C18−62.4 (3)C22—C23—N3—C28−66.9 (3)
C15—C16—C17—C18175.5 (2)O2—C8—O1—C72.9 (5)
C16—C17—C18—C19−73.4 (4)C9—C8—O1—C7178.9 (3)
C16—C17—C18—C20161.9 (3)C6—C7—O1—C8−178.8 (3)
O4—C22—C23—N3−38.3 (3)O5—C28—O6—C29−3.9 (4)
N2—C22—C23—N3143.3 (2)N3—C28—O6—C29176.7 (2)
O4—C22—C23—C2483.5 (3)C32—C29—O6—C28−65.8 (3)
N2—C22—C23—C24−94.8 (3)C30—C29—O6—C2858.8 (4)
N3—C23—C24—C25−62.9 (3)C31—C29—O6—C28175.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O3i0.882.092.923 (3)157
C2—H2···O4ii0.952.573.499 (5)166
C18—H18···O51.002.573.560 (4)163
C9—H9···O40.992.333.309 (4)164

Symmetry codes: (i) −x+1, −x+y, −z+1/3; (ii) −x+1, −x+y+1, −z+1/3.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2119).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liao, X.-J., Xu, W.-J., Xu, S.-H. & Dong, F.-F. (2007). Acta Cryst. E63, o3313.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Xu, W.-J., Liao, X.-J., Xu, S.-H., Diao, J.-Z., Du, B., Zhou, X.-L. & Pan, S.-S. (2008). Org. Lett.10, 4569–4572. [PubMed]

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