PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1867.
Published online 2010 June 30. doi:  10.1107/S1600536810024256
PMCID: PMC3006722

N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclo­hepten-2-yl)amino]­phen­yl}benzamide

Abstract

In the title compound, C29H24N2O2, the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 32.27 (8)°. In the crystal N—H(...)O hydrogen bonds link the mol­ecules into chains along the a axis. Further N—H(...)·O inter­actions link the chains.

Related literature

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004 [triangle]); Grasa et al. (2001 [triangle]). For p38 MAP kinase inhibitors based on dibenzosuberones, see: Laufer et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1867-scheme1.jpg

Experimental

Crystal data

  • C29H24N2O2
  • M r = 432.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1867-efi1.jpg
  • a = 8.5878 (6) Å
  • b = 17.0342 (12) Å
  • c = 30.669 (2) Å
  • V = 4486.4 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 K
  • 0.50 × 0.13 × 0.06 mm

Data collection

  • Bruker SMART APEXIIdiffractometer
  • 54075 measured reflections
  • 5388 independent reflections
  • 3740 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.119
  • S = 1.00
  • 5388 reflections
  • 301 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024256/zl2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024256/zl2285Isup2.hkl

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

supplementary crystallographic information

Comment

Recently we designed and synthesized a series of p38 MAP kinase inhibitors based on dibenzosuberones (Laufer et al. 2006). The title compound was synthesized in the course of our ongoing studies on dibenzo[a,d]cycloheptan-5-ones as potent p38 mitogen-activated protein (MAP) kinase inhibitors.

The structure of the title compound, at 173 (2) K has orthorhombic symmetry. In the molecule (Fig.1), rings A (C1—C4, C14, C15) and B (C6—C11) are, of course, planar and they are oriented at a dihedral angle of A/B = 32.27 (8)°. In the crystal structure N17—H17···O16 (2.89 (2) Å) forms a chain parallel to the a-axis and N25—H25···O27 (2.86 (2) Å) links two by the c-glide plane related chains together (Fig.2).

Experimental

For the preparation of the title compound a mixture of 500 mg (2.1 mmol) 2-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, 470 mg (2.1 mmol) N-(5-amino-2-methylphenyl)benzamide, 940 mg (8.4 mmol) KOtert-Bu, 90 mg (0.19 mmol) 2-(dicyclohexylphosphino)-2'-, 4'-, 6'-triisopropylbiphenyl and 20 mg (0.09 mmol) Pd(OAc)2 in 3 ml absolute tert-butanol and 7 ml absolute toluol was stirred for 3 h at 264 K (90 °C) under an atmosphere of argon. The mixture was diluted with water then extracted with ethyl acetate. The extracts were combined, washed with saturated saline solution, dried over Na2SO4 and then evaporated under reduced pressure. The residue was purified by flash chromatography (SiO2 60, n-hexane / ethyl acetate 7 + 3) (yield: 16.3%). Crystals of the title compound were obtained by slow evaporation of a acetone / ethyl acetate / diethyl ether solution at room temperature. IR (ATR): 3312, 1648, 1575, 1544, 1511, 1292, 1275, 1263, 1109, 763, 701, 689cm-1. 1H-NMR (DMSO-d6) d in ppm: 2.21 (s, 3H), 3.07 (s, 4H), 6.87-7.04 (m, 3H), 7.20-7.59 (m, 8H), 7.84 (d, J=7.8 Hz, 1H), 7.96-8.01 (m, 3H), 8.80 (s, 1H, NH), 9.83 (s, 1H, NH). 13C-NMR (DMSO-d6) d in ppm: 17.7, 34.4, 36.2, 112.9, 114.3, 118.0, 118.3, 126.8, 127.3, 127.5, 128.0 (x2), 128.8 (x2), 129.0, 130.5, 131.3, 131.9, 132.2, 133.8, 135.0, 137.3, 139.3, 139.4, 142.0, 145.8, 149.0, 165.7, 191.0. HRMS-ESI, m/z (C29H24N2O2): calcd, 432.1838 [M+H]+; found, 432.1860.

1H NMR (200 MHz) and 13C NMR (50 MHz) were recorded on a Bruker Advance 200. IR data were determined on a Perkin-Elmer Spectrum One spectrometer (ATR technique). HRMS (EI) (electron impact – high resolution mass spectroscopy) data were obtained from the department for mass spectrometry, Institute of Organic chemistry, Eberhard-Karls-University Tübingen.

Refinement

Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (sp3 C-atom). Hydrogen atoms attached to N17 and N25 were located in diff. Fourier maps and refined using the AFIX 4 constraint (N-H distance is free to refine) with Uiso(H) = 1.2Ueq(N). All H atoms attached to carbon atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq(C) of the parent atom).

Figures

Fig. 1.
View of compound the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Part of the packing diagram illustrating the hydrogen bonds. View along the b-axis.

Crystal data

C29H24N2O2F(000) = 1824
Mr = 432.50Dx = 1.281 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 6479 reflections
a = 8.5878 (6) Åθ = 2.4–24.1°
b = 17.0342 (12) ŵ = 0.08 mm1
c = 30.669 (2) ÅT = 173 K
V = 4486.4 (5) Å3Plate, yellow
Z = 80.50 × 0.13 × 0.06 mm

Data collection

Bruker SMART APEXII diffractometer3740 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.069
graphiteθmax = 27.9°, θmin = 2.4°
CCD scanh = −11→11
54075 measured reflectionsk = −21→22
5388 independent reflectionsl = −40→39

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0522P)2 + 1.6792P] where P = (Fo2 + 2Fc2)/3
5388 reflections(Δ/σ)max = 0.002
301 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.19 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.56067 (17)0.43978 (9)0.43200 (5)0.0264 (3)
C20.42391 (17)0.45759 (10)0.40902 (5)0.0303 (4)
H20.42940.48100.38100.036*
C30.28200 (17)0.44081 (10)0.42747 (5)0.0294 (3)
H30.19050.45390.41170.035*
C40.26547 (17)0.40522 (9)0.46867 (5)0.0266 (3)
C50.10305 (18)0.39527 (9)0.48427 (5)0.0291 (3)
C60.05457 (17)0.35895 (9)0.52689 (5)0.0278 (3)
C7−0.08844 (18)0.38403 (10)0.54369 (5)0.0327 (4)
H7−0.14290.42520.52940.039*
C8−0.1525 (2)0.35043 (11)0.58062 (5)0.0382 (4)
H8−0.24910.36890.59170.046*
C9−0.0751 (2)0.28965 (11)0.60145 (6)0.0416 (4)
H9−0.11970.26520.62630.050*
C100.0673 (2)0.26490 (10)0.58569 (6)0.0375 (4)
H100.12080.22390.60040.045*
C110.13471 (18)0.29860 (9)0.54876 (5)0.0295 (3)
C120.29383 (19)0.27248 (9)0.53467 (6)0.0332 (4)
H12A0.28760.24890.50520.040*
H12B0.33290.23190.55500.040*
C130.40667 (18)0.34182 (10)0.53394 (5)0.0308 (4)
H13A0.37970.37830.55790.037*
H13B0.51360.32230.53930.037*
C140.40373 (17)0.38601 (9)0.49132 (5)0.0249 (3)
C150.54564 (17)0.40451 (9)0.47287 (5)0.0260 (3)
H150.63760.39270.48880.031*
O16−0.00360 (13)0.42043 (8)0.46106 (4)0.0426 (3)
N170.70774 (15)0.45536 (8)0.41644 (4)0.0314 (3)
H170.7877 (18)0.45103 (13)0.4342 (4)0.038*
C180.74679 (17)0.47550 (9)0.37302 (5)0.0272 (3)
C190.68395 (17)0.43432 (9)0.33809 (5)0.0266 (3)
H190.61490.39170.34330.032*
C200.72163 (16)0.45516 (9)0.29563 (5)0.0254 (3)
C210.82292 (18)0.51809 (9)0.28699 (5)0.0297 (3)
C220.89126 (19)0.55434 (10)0.32282 (6)0.0350 (4)
H220.96620.59440.31790.042*
C230.85449 (18)0.53435 (10)0.36533 (5)0.0332 (4)
H230.90270.56080.38900.040*
C240.8502 (2)0.54853 (11)0.24131 (6)0.0401 (4)
H24A0.90540.59880.24270.060*
H24B0.74990.55590.22660.060*
H24C0.91300.51060.22490.060*
N250.66532 (14)0.41082 (8)0.25969 (4)0.0283 (3)
H250.7321 (14)0.3984 (3)0.2380 (5)0.034*
C260.53364 (17)0.36762 (9)0.25892 (5)0.0277 (3)
O270.43664 (12)0.36770 (7)0.28857 (4)0.0352 (3)
C280.51003 (18)0.31897 (10)0.21871 (5)0.0301 (4)
C290.4196 (2)0.25209 (11)0.22279 (6)0.0466 (5)
H290.37470.23900.25010.056*
C300.3948 (3)0.20449 (13)0.18704 (7)0.0627 (6)
H300.33530.15780.19010.075*
C310.4558 (3)0.22431 (13)0.14716 (7)0.0577 (6)
H310.43800.19130.12270.069*
C320.5426 (2)0.29157 (13)0.14238 (6)0.0496 (5)
H320.58290.30550.11460.060*
C330.5709 (2)0.33890 (12)0.17818 (6)0.0385 (4)
H330.63210.38500.17510.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0229 (7)0.0303 (8)0.0260 (8)0.0015 (6)−0.0023 (6)−0.0063 (6)
C20.0257 (8)0.0420 (9)0.0232 (8)0.0040 (7)−0.0026 (6)0.0007 (7)
C30.0229 (8)0.0403 (9)0.0248 (8)0.0057 (6)−0.0060 (6)−0.0025 (7)
C40.0232 (7)0.0314 (8)0.0252 (8)0.0016 (6)−0.0037 (6)−0.0038 (6)
C50.0239 (8)0.0335 (8)0.0300 (8)0.0000 (6)−0.0058 (6)−0.0047 (7)
C60.0235 (7)0.0324 (8)0.0274 (8)−0.0059 (6)−0.0030 (6)−0.0078 (6)
C70.0257 (8)0.0392 (9)0.0330 (9)−0.0041 (7)−0.0041 (7)−0.0088 (7)
C80.0281 (8)0.0500 (11)0.0364 (10)−0.0085 (8)0.0030 (7)−0.0108 (8)
C90.0409 (10)0.0458 (11)0.0380 (10)−0.0154 (8)0.0058 (8)−0.0030 (8)
C100.0412 (10)0.0314 (9)0.0397 (10)−0.0072 (7)0.0003 (8)−0.0008 (7)
C110.0302 (8)0.0267 (8)0.0315 (8)−0.0049 (6)−0.0016 (7)−0.0057 (6)
C120.0348 (9)0.0298 (8)0.0350 (9)0.0036 (7)−0.0006 (7)0.0012 (7)
C130.0258 (8)0.0375 (9)0.0292 (8)0.0037 (7)−0.0034 (7)0.0034 (7)
C140.0249 (7)0.0251 (7)0.0248 (8)0.0020 (6)−0.0034 (6)−0.0048 (6)
C150.0224 (7)0.0307 (8)0.0249 (8)0.0038 (6)−0.0073 (6)−0.0044 (6)
O160.0218 (6)0.0675 (9)0.0384 (7)0.0022 (6)−0.0066 (5)0.0083 (6)
N170.0207 (6)0.0500 (9)0.0235 (7)0.0001 (6)−0.0050 (5)−0.0013 (6)
C180.0203 (7)0.0350 (8)0.0263 (8)0.0023 (6)−0.0020 (6)−0.0018 (6)
C190.0193 (7)0.0315 (8)0.0292 (8)−0.0014 (6)−0.0010 (6)−0.0007 (6)
C200.0183 (7)0.0313 (8)0.0266 (8)0.0007 (6)−0.0017 (6)−0.0035 (6)
C210.0250 (8)0.0324 (8)0.0317 (8)−0.0010 (6)0.0027 (7)0.0006 (7)
C220.0298 (9)0.0342 (9)0.0411 (10)−0.0095 (7)0.0014 (7)−0.0031 (7)
C230.0272 (8)0.0388 (9)0.0336 (9)−0.0039 (7)−0.0041 (7)−0.0094 (7)
C240.0409 (10)0.0405 (10)0.0390 (10)−0.0062 (8)0.0048 (8)0.0061 (8)
N250.0202 (6)0.0398 (8)0.0248 (7)−0.0032 (5)0.0022 (5)−0.0048 (6)
C260.0211 (7)0.0364 (9)0.0255 (8)−0.0003 (6)−0.0022 (6)0.0008 (6)
O270.0225 (5)0.0576 (8)0.0253 (6)−0.0072 (5)0.0001 (5)−0.0021 (5)
C280.0229 (7)0.0383 (9)0.0291 (8)0.0008 (7)−0.0061 (6)−0.0029 (7)
C290.0565 (12)0.0457 (11)0.0377 (10)−0.0158 (9)−0.0097 (9)0.0012 (8)
C300.0861 (17)0.0457 (12)0.0562 (14)−0.0244 (12)−0.0216 (12)−0.0030 (10)
C310.0736 (15)0.0564 (13)0.0431 (12)0.0011 (11)−0.0194 (11)−0.0191 (10)
C320.0470 (11)0.0682 (14)0.0337 (10)0.0006 (10)−0.0015 (9)−0.0120 (9)
C330.0311 (9)0.0524 (11)0.0320 (9)−0.0058 (8)−0.0004 (7)−0.0061 (8)

Geometric parameters (Å, °)

C1—N171.3760 (19)N17—H170.880 (19)
C1—C151.396 (2)C18—C231.384 (2)
C1—C21.403 (2)C18—C191.390 (2)
C2—C31.374 (2)C19—C201.388 (2)
C2—H20.9500C19—H190.9500
C3—C41.409 (2)C20—C211.406 (2)
C3—H30.9500C20—N251.4210 (19)
C4—C141.414 (2)C21—C221.390 (2)
C4—C51.484 (2)C21—C241.512 (2)
C5—O161.2366 (19)C22—C231.384 (2)
C5—C61.505 (2)C22—H220.9500
C6—C71.399 (2)C23—H230.9500
C6—C111.407 (2)C24—H24A0.9800
C7—C81.383 (2)C24—H24B0.9800
C7—H70.9500C24—H24C0.9800
C8—C91.386 (3)N25—C261.3494 (19)
C8—H80.9500N25—H250.905 (18)
C9—C101.381 (3)C26—O271.2334 (18)
C9—H90.9500C26—C281.499 (2)
C10—C111.395 (2)C28—C291.384 (2)
C10—H100.9500C28—C331.391 (2)
C11—C121.501 (2)C29—C301.380 (3)
C12—C131.528 (2)C29—H290.9500
C12—H12A0.9900C30—C311.373 (3)
C12—H12B0.9900C30—H300.9500
C13—C141.509 (2)C31—C321.374 (3)
C13—H13A0.9900C31—H310.9500
C13—H13B0.9900C32—C331.384 (2)
C14—C151.380 (2)C32—H320.9500
C15—H150.9500C33—H330.9500
N17—C181.415 (2)
N17—C1—C15118.63 (13)C1—N17—C18126.19 (13)
N17—C1—C2123.55 (14)C1—N17—H17118.98 (8)
C15—C1—C2117.82 (14)C18—N17—H17114.78 (8)
C3—C2—C1119.41 (15)C23—C18—C19119.58 (14)
C3—C2—H2120.3C23—C18—N17119.62 (14)
C1—C2—H2120.3C19—C18—N17120.73 (14)
C2—C3—C4123.25 (14)C20—C19—C18120.25 (14)
C2—C3—H3118.4C20—C19—H19119.9
C4—C3—H3118.4C18—C19—H19119.9
C3—C4—C14117.11 (14)C19—C20—C21121.08 (14)
C3—C4—C5115.65 (13)C19—C20—N25120.82 (14)
C14—C4—C5127.18 (14)C21—C20—N25118.02 (13)
O16—C5—C4118.09 (14)C22—C21—C20116.81 (14)
O16—C5—C6115.95 (14)C22—C21—C24120.97 (15)
C4—C5—C6125.93 (13)C20—C21—C24122.13 (14)
C7—C6—C11118.48 (15)C23—C22—C21122.61 (15)
C7—C6—C5115.94 (14)C23—C22—H22118.7
C11—C6—C5125.38 (14)C21—C22—H22118.7
C8—C7—C6121.63 (16)C22—C23—C18119.42 (15)
C8—C7—H7119.2C22—C23—H23120.3
C6—C7—H7119.2C18—C23—H23120.3
C7—C8—C9119.75 (16)C21—C24—H24A109.5
C7—C8—H8120.1C21—C24—H24B109.5
C9—C8—H8120.1H24A—C24—H24B109.5
C10—C9—C8119.40 (17)C21—C24—H24C109.5
C10—C9—H9120.3H24A—C24—H24C109.5
C8—C9—H9120.3H24B—C24—H24C109.5
C9—C10—C11121.72 (17)C26—N25—C20126.07 (13)
C9—C10—H10119.1C26—N25—H25113.04 (9)
C11—C10—H10119.1C20—N25—H25118.67 (8)
C10—C11—C6118.99 (15)O27—C26—N25123.53 (14)
C10—C11—C12119.30 (15)O27—C26—C28121.05 (14)
C6—C11—C12121.65 (14)N25—C26—C28115.42 (13)
C11—C12—C13110.64 (13)C29—C28—C33119.51 (16)
C11—C12—H12A109.5C29—C28—C26117.15 (15)
C13—C12—H12A109.5C33—C28—C26123.32 (15)
C11—C12—H12B109.5C30—C29—C28119.88 (19)
C13—C12—H12B109.5C30—C29—H29120.1
H12A—C12—H12B108.1C28—C29—H29120.1
C14—C13—C12112.82 (13)C31—C30—C29120.3 (2)
C14—C13—H13A109.0C31—C30—H30119.9
C12—C13—H13A109.0C29—C30—H30119.9
C14—C13—H13B109.0C30—C31—C32120.45 (18)
C12—C13—H13B109.0C30—C31—H31119.8
H13A—C13—H13B107.8C32—C31—H31119.8
C15—C14—C4119.15 (14)C31—C32—C33119.76 (19)
C15—C14—C13117.03 (13)C31—C32—H32120.1
C4—C14—C13123.73 (14)C33—C32—H32120.1
C14—C15—C1123.23 (14)C32—C33—C28120.05 (17)
C14—C15—H15118.4C32—C33—H33120.0
C1—C15—H15118.4C28—C33—H33120.0
N17—C1—C2—C3−179.11 (15)N17—C1—C15—C14−179.60 (14)
C15—C1—C2—C30.7 (2)C2—C1—C15—C140.5 (2)
C1—C2—C3—C4−0.8 (3)C15—C1—N17—C18166.23 (15)
C2—C3—C4—C14−0.4 (2)C2—C1—N17—C18−13.9 (3)
C2—C3—C4—C5177.03 (15)C1—N17—C18—C23137.86 (17)
C3—C4—C5—O16−2.0 (2)C1—N17—C18—C19−45.3 (2)
C14—C4—C5—O16175.13 (15)C23—C18—C19—C20−3.9 (2)
C3—C4—C5—C6179.85 (14)N17—C18—C19—C20179.24 (14)
C14—C4—C5—C6−3.0 (3)C18—C19—C20—C21−0.3 (2)
O16—C5—C6—C7−24.6 (2)C18—C19—C20—N25176.39 (14)
C4—C5—C6—C7153.62 (15)C19—C20—C21—C224.4 (2)
O16—C5—C6—C11150.24 (16)N25—C20—C21—C22−172.33 (14)
C4—C5—C6—C11−31.6 (2)C19—C20—C21—C24−172.18 (15)
C11—C6—C7—C8−0.7 (2)N25—C20—C21—C2411.1 (2)
C5—C6—C7—C8174.43 (14)C20—C21—C22—C23−4.7 (2)
C6—C7—C8—C9−0.9 (2)C24—C21—C22—C23171.97 (16)
C7—C8—C9—C101.8 (3)C21—C22—C23—C180.7 (3)
C8—C9—C10—C11−1.1 (3)C19—C18—C23—C223.7 (2)
C9—C10—C11—C6−0.5 (2)N17—C18—C23—C22−179.41 (15)
C9—C10—C11—C12176.51 (15)C19—C20—N25—C2626.7 (2)
C7—C6—C11—C101.4 (2)C21—C20—N25—C26−156.54 (15)
C5—C6—C11—C10−173.26 (14)C20—N25—C26—O277.6 (3)
C7—C6—C11—C12−175.52 (14)C20—N25—C26—C28−173.21 (14)
C5—C6—C11—C129.8 (2)O27—C26—C28—C29−26.9 (2)
C10—C11—C12—C13−121.01 (16)N25—C26—C28—C29153.85 (16)
C6—C11—C12—C1355.9 (2)O27—C26—C28—C33151.57 (17)
C11—C12—C13—C14−86.65 (17)N25—C26—C28—C33−27.7 (2)
C3—C4—C14—C151.6 (2)C33—C28—C29—C302.1 (3)
C5—C4—C14—C15−175.47 (15)C26—C28—C29—C30−179.38 (18)
C3—C4—C14—C13−174.79 (14)C28—C29—C30—C31−1.8 (3)
C5—C4—C14—C138.1 (2)C29—C30—C31—C320.2 (4)
C12—C13—C14—C15−133.61 (14)C30—C31—C32—C331.2 (3)
C12—C13—C14—C442.9 (2)C31—C32—C33—C28−0.9 (3)
C4—C14—C15—C1−1.8 (2)C29—C28—C33—C32−0.7 (3)
C13—C14—C15—C1174.91 (14)C26—C28—C33—C32−179.17 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N17—H17···O16i0.88 (2)2.04 (2)2.8934 (18)163 (1)
N25—H25···O27ii0.91 (2)2.01 (2)2.8566 (17)156 (1)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2285).

References

  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Grasa, G. A., Viciu, M. S., Huang, J. & Nolan, S. P. (2001). J. Org. Chem.66, 7729–7737. [PubMed]
  • Jensen, T. A., Liang, X., Tanner, D. & Skjaerbaek, N. (2004). J. Org. Chem.69, 4936–4947. [PubMed]
  • Laufer, S. A., Ahrens, G. M., Karcher, S. C., Hering, J. S. & Niess, R. (2006). J. Med. Chem.49, 7912–7915. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography