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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2042.
Published online 2008 September 30. doi:  10.1107/S1600536808030961
PMCID: PMC2959299

Ethyl 1-(4-chloro­phen­yl)-3-[1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-2-nitro-2,3,10,10a-tetra­hydro-1H,5H-pyr­rolo[1,2-b]isoquinoline-10a-carboxyl­ate

Abstract

In the title compound, C37H34ClN3O6, the pyrrolidine and piperidine rings adopt envelope and boat conformations, respectively. The β-lactam ring is planar and forms dihedral angles of 21.3 (2) and 73.9 (2)°, respectively, with the attached methoxy­phenyl and phenyl rings. Intra­molecular C—H(...)O and C—H(...)N hydrogen bonds are observed. Centrosym­metrically related mol­ecules are linked together by weak C—H(...)O hydrogen bonds to form dimers.

Related literature

For the biological properties of β-lactam derivatives, see: Borthwick et al. (1998 [triangle]); Brakhage (1998 [triangle]); Burnett (1994 [triangle]); Han et al. (1995 [triangle]); Vaccaro & Davis (1998 [triangle]); Vaccaro et al. (1998 [triangle]). For puckering and asymmetry parameters, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2042-scheme1.jpg

Experimental

Crystal data

  • C37H34ClN3O6
  • M r = 652.12
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2042-efi1.jpg
  • a = 9.1723 (2) Å
  • b = 18.0452 (4) Å
  • c = 19.7475 (5) Å
  • β = 100.638 (1)°
  • V = 3212.35 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 293 (2) K
  • 0.22 × 0.20 × 0.17 mm

Data collection

  • Bruker kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.963, T max = 0.971
  • 30325 measured reflections
  • 5582 independent reflections
  • 3760 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.135
  • S = 1.02
  • 5582 reflections
  • 426 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030961/ci2676sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030961/ci2676Isup2.hkl

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

Acknowledgments

SS thanks Dr Babu Varghese, SAIF, IIT Madras, Chennai, India, for his help with the data collection.

supplementary crystallographic information

Comment

β-Lactams have been shown to exhibit high antibacterial activity. 1,3,4-Trisubstituted β-lactams are potent cholesterol absorption inhibitors (Vaccaro & Davis, 1998; Vaccaro et al., 1998; Burnett, 1994), human cylomegalonims and protease inhibitors (Borthwick et al., 1998) and thrombin inhibitors (Han et al., 1995). The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporins (Brakhage, 1998). In view of these importance, the crystal structure determination of the title compound was carried out.

The pyrrolidine and piperidine rings in the molecule adopt envelope and boat conformations, respectively. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameter (Nardelli, 1983) for the pyrrolidine ring are q2 = 0.292 (3) Å, π = 99.6 (5)° and ΔS(C12) = 4.4 (3)°, and for the piperidine ring q2 = 0.630 (3) Å, q3 = 0.004 (3) Å, π = 61.2 (2)° and ΔS(C2) = ΔS(C9) = 1.2 (2)°. The ethylcarboxylate group adopts an extended conformation. The sum of angles at atom N27 of the β-lactam ring system [356.9°] is in accordance with sp2 hybridization. The β-lactam ring is planar and the keto O5 atom deviates from this plane by -0.005 (2) Å. The methoxyphenyl (C34—C39) and (C28—C33) phenyl rings form dihedral angles of 21.3 (2) and 73.9 (2)°, respectively, with the β-lactam ring. C—H···O and C—H···N types of intramolecular hydrogen bonds are observed.

In the crystal structure, atoms C25 and C40 of the molecule at (x, y, z) donate one proton each to atoms O6 and O4 of the molecule at (- x, 1 - y, -z), forming a cyclic centrosymmetric dimer.

Experimental

To a stirred solution of 5-[1'-N-(p-methoxyphenyl-azetidine-2'-one]-4-nitro-3-(p-chloro)-phenyl-2-ethoxycarbonyl-2-benzyl-pyrrlolidine (1 mmol) in dry chloroform (20 ml) para formaldehyde (1 mmol) and then trifluroacetic acid (0.1 mmol) were added at room temperature. After completion of the reaction, the mixture was washed with water and dried over. The solvent was removed under the reduced pressure and the crude product was subjected to column chromatography with hexane-ethyl acetate (9:1) to obtain pure cyclized product. The compound was recrystallized from ethyl acetate

Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. Large thermal vibrations of atoms C15 and C16 resulted in the shortening of C15—C16 length.

Figures

Fig. 1.
The molecular structure of the title compound, showing 20% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C37H34ClN3O6F(000) = 1368
Mr = 652.12Dx = 1.348 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5002 reflections
a = 9.1723 (2) Åθ = 1.5–24.9°
b = 18.0452 (4) ŵ = 0.17 mm1
c = 19.7475 (5) ÅT = 293 K
β = 100.638 (1)°Block, colourless
V = 3212.35 (13) Å30.22 × 0.20 × 0.17 mm
Z = 4

Data collection

Bruker kappa APEXII area-detector diffractometer5582 independent reflections
Radiation source: fine-focus sealed tube3760 reflections with I > 2σ(I)
graphiteRint = 0.034
ω and [var phi] scansθmax = 24.9°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −10→10
Tmin = 0.963, Tmax = 0.971k = −20→21
30325 measured reflectionsl = −23→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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0537P)2 + 1.5127P] where P = (Fo2 + 2Fc2)/3
5582 reflections(Δ/σ)max = 0.001
426 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.27 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
Cl10.26960 (11)0.43479 (5)0.60642 (4)0.0979 (3)
O1−0.1144 (2)0.31964 (12)0.15686 (11)0.0870 (6)
O2−0.2380 (2)0.31467 (12)0.24445 (12)0.0914 (7)
O3−0.2459 (3)0.47487 (16)0.18822 (18)0.1215 (11)
O4−0.2416 (4)0.58070 (18)0.23474 (14)0.1523 (14)
O50.3329 (2)0.63293 (11)0.11354 (11)0.0839 (6)
O60.2021 (2)0.31726 (12)−0.07279 (10)0.0823 (6)
N10.08498 (19)0.41518 (10)0.21858 (10)0.0468 (5)
C20.2354 (3)0.38685 (14)0.21800 (13)0.0556 (6)
H2A0.28910.42290.19570.067*
H2B0.22800.34160.19110.067*
C30.3207 (3)0.37143 (13)0.28843 (13)0.0537 (6)
C40.4641 (3)0.39488 (18)0.31274 (17)0.0771 (8)
H40.51370.42300.28470.093*
C50.5336 (3)0.3767 (2)0.3782 (2)0.0940 (10)
H50.62950.39340.39470.113*
C60.4625 (4)0.33415 (19)0.41941 (17)0.0836 (9)
H60.51130.32090.46330.100*
C70.3198 (3)0.31095 (14)0.39631 (14)0.0644 (7)
H70.27140.28240.42460.077*
C80.2481 (3)0.33003 (12)0.33104 (13)0.0499 (6)
C90.0928 (3)0.30842 (12)0.30105 (13)0.0547 (6)
H9A0.04410.29090.33770.066*
H9B0.09450.26780.26900.066*
C100.0017 (2)0.37342 (12)0.26295 (12)0.0487 (6)
C11−0.0500 (3)0.43205 (12)0.31170 (13)0.0513 (6)
H11−0.15450.42220.31320.062*
C12−0.0423 (3)0.50536 (13)0.27378 (13)0.0551 (6)
H12−0.01620.54570.30700.066*
C130.0807 (3)0.49450 (12)0.23229 (12)0.0479 (5)
H130.17470.50790.26210.058*
C14−0.1333 (3)0.33509 (15)0.22050 (16)0.0654 (7)
C15−0.2295 (5)0.2774 (2)0.1122 (2)0.1293 (16)
H15A−0.18310.23950.08860.155*
H15B−0.29110.25280.14030.155*
C16−0.3162 (5)0.3200 (3)0.0650 (2)0.163 (2)
H16A−0.37040.35440.08800.245*
H16B−0.38460.28910.03480.245*
H16C−0.25540.34670.03870.245*
C170.0339 (3)0.43451 (12)0.38492 (13)0.0522 (6)
C18−0.0165 (3)0.39231 (14)0.43459 (14)0.0624 (7)
H18−0.10110.36340.42200.075*
C190.0560 (3)0.39233 (16)0.50219 (15)0.0717 (8)
H190.02070.36350.53480.086*
C200.1801 (3)0.43493 (16)0.52118 (14)0.0677 (8)
C210.2316 (3)0.47828 (15)0.47366 (15)0.0696 (7)
H210.31530.50770.48690.083*
C220.1586 (3)0.47789 (14)0.40612 (13)0.0610 (7)
H220.19380.50740.37400.073*
N23−0.1895 (3)0.52072 (17)0.22867 (14)0.0772 (8)
C240.0636 (3)0.54308 (12)0.16801 (12)0.0512 (6)
H24−0.03720.54120.14090.061*
C250.1223 (3)0.62490 (13)0.18009 (13)0.0559 (6)
H250.04960.65930.15460.067*
C260.2339 (3)0.60255 (14)0.13526 (13)0.0611 (7)
N270.1771 (2)0.53255 (11)0.12491 (10)0.0555 (5)
C280.1739 (3)0.65324 (12)0.25172 (13)0.0547 (6)
C290.3113 (3)0.63541 (14)0.28979 (16)0.0678 (7)
H290.37700.60730.26980.081*
C300.3525 (4)0.65882 (17)0.35720 (18)0.0828 (9)
H300.44480.64560.38230.099*
C310.2596 (4)0.70088 (18)0.38705 (18)0.0861 (9)
H310.28770.71630.43250.103*
C320.1253 (4)0.72025 (16)0.35001 (18)0.0813 (9)
H320.06160.74940.37030.098*
C330.0822 (3)0.69735 (14)0.28273 (16)0.0665 (7)
H33−0.00970.71180.25790.080*
C340.1861 (3)0.47852 (13)0.07403 (12)0.0533 (6)
C350.3076 (3)0.47553 (16)0.04257 (15)0.0700 (8)
H350.38430.50940.05470.084*
C360.3168 (3)0.42258 (16)−0.00697 (15)0.0725 (8)
H360.39910.4213−0.02830.087*
C370.2053 (3)0.37216 (15)−0.02476 (13)0.0596 (6)
C380.0838 (3)0.37514 (15)0.00705 (13)0.0612 (7)
H380.00730.3411−0.00500.073*
C390.0741 (3)0.42744 (14)0.05597 (13)0.0573 (6)
H39−0.00840.42860.07720.069*
C400.3268 (3)0.30843 (19)−0.10496 (16)0.0824 (9)
H40A0.34770.3545−0.12560.124*
H40B0.30620.2710−0.13990.124*
H40C0.41120.2939−0.07120.124*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1261 (7)0.1070 (6)0.0593 (5)0.0466 (5)0.0135 (5)−0.0010 (4)
O10.0823 (14)0.1021 (16)0.0680 (14)−0.0362 (12)−0.0090 (11)0.0012 (11)
O20.0641 (13)0.0896 (15)0.1228 (19)−0.0263 (11)0.0235 (12)0.0104 (13)
O30.0639 (15)0.0989 (19)0.183 (3)−0.0030 (13)−0.0253 (17)0.0309 (19)
O40.183 (3)0.162 (3)0.107 (2)0.128 (2)0.0138 (19)0.0210 (18)
O50.0955 (15)0.0691 (12)0.0985 (16)−0.0293 (11)0.0479 (13)−0.0002 (11)
O60.0805 (13)0.0942 (15)0.0781 (14)−0.0059 (11)0.0301 (11)−0.0264 (11)
N10.0446 (11)0.0440 (10)0.0542 (12)0.0015 (8)0.0153 (9)0.0028 (8)
C20.0516 (14)0.0588 (14)0.0607 (16)0.0085 (11)0.0215 (12)−0.0004 (12)
C30.0449 (14)0.0546 (14)0.0628 (16)0.0097 (11)0.0132 (12)−0.0047 (12)
C40.0477 (16)0.090 (2)0.096 (2)0.0049 (14)0.0180 (16)0.0048 (17)
C50.0507 (18)0.113 (3)0.109 (3)0.0087 (18)−0.0078 (19)−0.001 (2)
C60.075 (2)0.094 (2)0.073 (2)0.0268 (18)−0.0099 (17)−0.0029 (18)
C70.0673 (18)0.0575 (15)0.0676 (18)0.0192 (13)0.0107 (14)0.0045 (13)
C80.0523 (14)0.0401 (12)0.0574 (15)0.0105 (10)0.0102 (12)−0.0025 (11)
C90.0590 (15)0.0438 (13)0.0624 (16)0.0010 (11)0.0135 (12)0.0045 (11)
C100.0460 (13)0.0449 (12)0.0570 (15)−0.0022 (10)0.0147 (11)0.0061 (10)
C110.0448 (13)0.0510 (13)0.0624 (16)0.0063 (10)0.0210 (12)0.0128 (11)
C120.0566 (15)0.0506 (13)0.0628 (16)0.0099 (11)0.0235 (12)0.0121 (11)
C130.0506 (13)0.0434 (12)0.0524 (14)0.0012 (10)0.0165 (11)0.0047 (10)
C140.0532 (16)0.0605 (16)0.080 (2)−0.0077 (12)0.0061 (14)0.0148 (14)
C150.116 (3)0.118 (3)0.126 (3)−0.056 (3)−0.049 (3)0.015 (3)
C160.147 (4)0.197 (5)0.117 (4)−0.089 (4)−0.054 (3)0.056 (4)
C170.0563 (15)0.0456 (13)0.0607 (16)0.0136 (11)0.0268 (12)0.0062 (11)
C180.0636 (16)0.0617 (16)0.0685 (18)0.0128 (12)0.0291 (14)0.0159 (13)
C190.085 (2)0.0726 (18)0.0664 (19)0.0274 (16)0.0365 (17)0.0206 (15)
C200.084 (2)0.0662 (17)0.0564 (17)0.0298 (16)0.0217 (15)0.0001 (14)
C210.081 (2)0.0640 (17)0.0662 (19)0.0074 (14)0.0208 (16)−0.0104 (14)
C220.0775 (18)0.0541 (15)0.0570 (17)0.0032 (13)0.0275 (14)−0.0006 (12)
N230.0689 (17)0.0873 (19)0.0842 (19)0.0343 (15)0.0372 (15)0.0408 (15)
C240.0510 (14)0.0512 (13)0.0535 (14)−0.0018 (10)0.0155 (11)0.0061 (11)
C250.0631 (16)0.0464 (13)0.0597 (16)−0.0005 (11)0.0150 (13)0.0100 (11)
C260.0712 (17)0.0539 (15)0.0612 (16)−0.0088 (13)0.0204 (14)0.0096 (12)
N270.0630 (13)0.0520 (12)0.0564 (13)−0.0118 (9)0.0240 (10)0.0015 (9)
C280.0599 (16)0.0421 (13)0.0632 (16)−0.0049 (11)0.0139 (13)0.0076 (11)
C290.0655 (18)0.0538 (15)0.084 (2)−0.0015 (13)0.0131 (16)0.0007 (14)
C300.078 (2)0.0727 (19)0.089 (2)−0.0049 (16)−0.0078 (18)−0.0006 (17)
C310.103 (3)0.075 (2)0.077 (2)−0.0136 (19)0.006 (2)−0.0069 (17)
C320.098 (2)0.0653 (18)0.089 (2)−0.0054 (17)0.037 (2)−0.0132 (16)
C330.0673 (17)0.0526 (15)0.082 (2)0.0022 (13)0.0190 (15)0.0036 (14)
C340.0600 (15)0.0546 (14)0.0485 (14)−0.0056 (11)0.0181 (12)0.0076 (11)
C350.0649 (17)0.0724 (18)0.079 (2)−0.0210 (14)0.0286 (15)−0.0059 (15)
C360.0656 (18)0.082 (2)0.079 (2)−0.0086 (15)0.0366 (15)−0.0050 (16)
C370.0623 (16)0.0672 (16)0.0516 (15)−0.0007 (13)0.0166 (13)−0.0013 (12)
C380.0623 (16)0.0690 (16)0.0545 (15)−0.0145 (13)0.0163 (13)−0.0038 (13)
C390.0551 (15)0.0685 (16)0.0522 (15)−0.0111 (12)0.0203 (12)0.0007 (12)
C400.079 (2)0.099 (2)0.0722 (19)0.0267 (17)0.0224 (16)−0.0084 (17)

Geometric parameters (Å, °)

Cl1—C201.731 (3)C16—H16C0.96
O1—C141.329 (3)C17—C221.385 (4)
O1—C151.460 (4)C17—C181.387 (3)
O2—C141.204 (3)C18—C191.377 (4)
O3—N231.199 (4)C18—H180.93
O4—N231.198 (3)C19—C201.368 (4)
O5—C261.205 (3)C19—H190.93
O6—C371.368 (3)C20—C211.371 (4)
O6—C401.416 (3)C21—C221.378 (4)
N1—C131.459 (3)C21—H210.93
N1—C101.472 (3)C22—H220.93
N1—C21.473 (3)C24—N271.474 (3)
C2—C31.491 (3)C24—C251.575 (3)
C2—H2A0.97C24—H240.98
C2—H2B0.97C25—C281.496 (3)
C3—C41.381 (4)C25—C261.526 (4)
C3—C81.384 (3)C25—H250.98
C4—C51.372 (4)C26—N271.367 (3)
C4—H40.93N27—C341.413 (3)
C5—C61.368 (5)C28—C331.381 (4)
C5—H50.93C28—C291.381 (4)
C6—C71.370 (4)C29—C301.381 (4)
C6—H60.93C29—H290.93
C7—C81.378 (3)C30—C311.354 (5)
C7—H70.93C30—H300.93
C8—C91.490 (3)C31—C321.357 (4)
C9—C101.552 (3)C31—H310.93
C9—H9A0.97C32—C331.378 (4)
C9—H9B0.97C32—H320.93
C10—C141.527 (4)C33—H330.93
C10—C111.562 (3)C34—C351.374 (3)
C11—C171.508 (3)C34—C391.377 (3)
C11—C121.528 (3)C35—C361.381 (4)
C11—H110.98C35—H350.93
C12—N231.500 (4)C36—C371.365 (4)
C12—C131.524 (3)C36—H360.93
C12—H120.98C37—C381.378 (3)
C13—C241.527 (3)C38—C391.365 (3)
C13—H130.98C38—H380.93
C15—C161.347 (5)C39—H390.93
C15—H15A0.97C40—H40A0.96
C15—H15B0.97C40—H40B0.96
C16—H16A0.96C40—H40C0.96
C16—H16B0.96
C14—O1—C15118.3 (3)C19—C18—H18119.3
C37—O6—C40118.5 (2)C17—C18—H18119.3
C13—N1—C10110.93 (17)C20—C19—C18119.6 (3)
C13—N1—C2113.53 (18)C20—C19—H19120.2
C10—N1—C2114.62 (17)C18—C19—H19120.2
N1—C2—C3112.88 (19)C19—C20—C21120.5 (3)
N1—C2—H2A109.0C19—C20—Cl1119.1 (2)
C3—C2—H2A109.0C21—C20—Cl1120.3 (3)
N1—C2—H2B109.0C20—C21—C22119.5 (3)
C3—C2—H2B109.0C20—C21—H21120.3
H2A—C2—H2B107.8C22—C21—H21120.3
C4—C3—C8119.2 (3)C21—C22—C17121.5 (2)
C4—C3—C2124.7 (2)C21—C22—H22119.3
C8—C3—C2116.0 (2)C17—C22—H22119.3
C5—C4—C3120.1 (3)O4—N23—O3124.0 (3)
C5—C4—H4120.0O4—N23—C12116.1 (3)
C3—C4—H4120.0O3—N23—C12119.9 (2)
C6—C5—C4120.3 (3)N27—C24—C13115.53 (19)
C6—C5—H5119.8N27—C24—C2587.13 (16)
C4—C5—H5119.8C13—C24—C25115.6 (2)
C5—C6—C7120.3 (3)N27—C24—H24112.1
C5—C6—H6119.8C13—C24—H24112.1
C7—C6—H6119.8C25—C24—H24112.1
C6—C7—C8119.8 (3)C28—C25—C26120.7 (2)
C6—C7—H7120.1C28—C25—C24120.22 (19)
C8—C7—H7120.1C26—C25—C2484.93 (18)
C7—C8—C3120.2 (2)C28—C25—H25109.6
C7—C8—C9124.2 (2)C26—C25—H25109.6
C3—C8—C9115.6 (2)C24—C25—H25109.6
C8—C9—C10112.61 (18)O5—C26—N27131.2 (3)
C8—C9—H9A109.1O5—C26—C25135.7 (2)
C10—C9—H9A109.1N27—C26—C2593.04 (19)
C8—C9—H9B109.1C26—N27—C34132.3 (2)
C10—C9—H9B109.1C26—N27—C2494.87 (18)
H9A—C9—H9B107.8C34—N27—C24129.76 (19)
N1—C10—C14111.3 (2)C33—C28—C29117.6 (3)
N1—C10—C9112.56 (18)C33—C28—C25120.3 (2)
C14—C10—C9103.48 (18)C29—C28—C25122.2 (2)
N1—C10—C11105.68 (17)C30—C29—C28120.8 (3)
C14—C10—C11109.7 (2)C30—C29—H29119.6
C9—C10—C11114.24 (19)C28—C29—H29119.6
C17—C11—C12112.5 (2)C31—C30—C29120.6 (3)
C17—C11—C10116.85 (18)C31—C30—H30119.7
C12—C11—C10103.73 (18)C29—C30—H30119.7
C17—C11—H11107.8C30—C31—C32119.4 (3)
C12—C11—H11107.8C30—C31—H31120.3
C10—C11—H11107.8C32—C31—H31120.3
N23—C12—C13112.3 (2)C31—C32—C33120.9 (3)
N23—C12—C11109.4 (2)C31—C32—H32119.6
C13—C12—C11104.96 (18)C33—C32—H32119.6
N23—C12—H12110.0C32—C33—C28120.7 (3)
C13—C12—H12110.0C32—C33—H33119.7
C11—C12—H12110.0C28—C33—H33119.7
N1—C13—C12105.89 (17)C35—C34—C39119.0 (2)
N1—C13—C24114.29 (19)C35—C34—N27120.5 (2)
C12—C13—C24113.61 (18)C39—C34—N27120.5 (2)
N1—C13—H13107.6C34—C35—C36120.5 (2)
C12—C13—H13107.6C34—C35—H35119.7
C24—C13—H13107.6C36—C35—H35119.7
O2—C14—O1124.0 (3)C37—C36—C35120.2 (2)
O2—C14—C10123.2 (3)C37—C36—H36119.9
O1—C14—C10112.3 (2)C35—C36—H36119.9
C16—C15—O1112.9 (3)C36—C37—O6125.5 (2)
C16—C15—H15A109.0C36—C37—C38119.1 (2)
O1—C15—H15A109.0O6—C37—C38115.4 (2)
C16—C15—H15B109.0C39—C38—C37120.9 (2)
O1—C15—H15B109.0C39—C38—H38119.6
H15A—C15—H15B107.8C37—C38—H38119.6
C15—C16—H16A109.5C38—C39—C34120.2 (2)
C15—C16—H16B109.5C38—C39—H39119.9
H16A—C16—H16B109.5C34—C39—H39119.9
C15—C16—H16C109.5O6—C40—H40A109.5
H16A—C16—H16C109.5O6—C40—H40B109.5
H16B—C16—H16C109.5H40A—C40—H40B109.5
C22—C17—C18117.5 (2)O6—C40—H40C109.5
C22—C17—C11123.6 (2)H40A—C40—H40C109.5
C18—C17—C11119.0 (2)H40B—C40—H40C109.5
C19—C18—C17121.4 (3)
C13—N1—C2—C382.0 (2)C18—C19—C20—C210.9 (4)
C10—N1—C2—C3−46.9 (3)C18—C19—C20—Cl1179.67 (19)
N1—C2—C3—C4−131.6 (3)C19—C20—C21—C22−0.9 (4)
N1—C2—C3—C848.9 (3)Cl1—C20—C21—C22−179.73 (19)
C8—C3—C4—C50.5 (4)C20—C21—C22—C17−0.1 (4)
C2—C3—C4—C5−179.0 (3)C18—C17—C22—C211.1 (3)
C3—C4—C5—C61.2 (5)C11—C17—C22—C21−180.0 (2)
C4—C5—C6—C7−1.8 (5)C13—C12—N23—O4−115.0 (3)
C5—C6—C7—C80.6 (4)C11—C12—N23—O4128.8 (3)
C6—C7—C8—C31.1 (4)C13—C12—N23—O363.0 (3)
C6—C7—C8—C9−179.4 (2)C11—C12—N23—O3−53.2 (3)
C4—C3—C8—C7−1.6 (3)N1—C13—C24—N27−56.2 (3)
C2—C3—C8—C7177.9 (2)C12—C13—C24—N27−177.9 (2)
C4—C3—C8—C9178.8 (2)N1—C13—C24—C25−155.91 (19)
C2—C3—C8—C9−1.6 (3)C12—C13—C24—C2582.4 (3)
C7—C8—C9—C10135.8 (2)N27—C24—C25—C28−123.9 (2)
C3—C8—C9—C10−44.7 (3)C13—C24—C25—C28−6.9 (3)
C13—N1—C10—C14115.2 (2)N27—C24—C25—C26−1.17 (17)
C2—N1—C10—C14−114.6 (2)C13—C24—C25—C26115.9 (2)
C13—N1—C10—C9−129.2 (2)C28—C25—C26—O5−58.7 (4)
C2—N1—C10—C91.0 (3)C24—C25—C26—O5179.0 (3)
C13—N1—C10—C11−3.9 (2)C28—C25—C26—N27123.6 (2)
C2—N1—C10—C11126.3 (2)C24—C25—C26—N271.27 (19)
C8—C9—C10—N144.5 (3)O5—C26—N27—C34−18.2 (5)
C8—C9—C10—C14164.7 (2)C25—C26—N27—C34159.6 (3)
C8—C9—C10—C11−76.0 (2)O5—C26—N27—C24−179.2 (3)
N1—C10—C11—C17−103.8 (2)C25—C26—N27—C24−1.4 (2)
C14—C10—C11—C17136.2 (2)C13—C24—N27—C26−115.8 (2)
C9—C10—C11—C1720.5 (3)C25—C24—N27—C261.31 (19)
N1—C10—C11—C1220.6 (2)C13—C24—N27—C3482.5 (3)
C14—C10—C11—C12−99.4 (2)C25—C24—N27—C34−160.4 (2)
C9—C10—C11—C12144.93 (19)C26—C25—C28—C33156.5 (2)
C17—C11—C12—N23−141.4 (2)C24—C25—C28—C33−100.4 (3)
C10—C11—C12—N2391.4 (2)C26—C25—C28—C29−25.0 (3)
C17—C11—C12—C1397.9 (2)C24—C25—C28—C2978.0 (3)
C10—C11—C12—C13−29.3 (2)C33—C28—C29—C302.3 (4)
C10—N1—C13—C12−14.7 (2)C25—C28—C29—C30−176.2 (2)
C2—N1—C13—C12−145.46 (19)C28—C29—C30—C31−1.1 (5)
C10—N1—C13—C24−140.51 (19)C29—C30—C31—C32−0.3 (5)
C2—N1—C13—C2488.7 (2)C30—C31—C32—C330.4 (5)
N23—C12—C13—N1−91.3 (2)C31—C32—C33—C280.9 (4)
C11—C12—C13—N127.5 (2)C29—C28—C33—C32−2.2 (4)
N23—C12—C13—C2435.0 (3)C25—C28—C33—C32176.3 (2)
C11—C12—C13—C24153.8 (2)C26—N27—C34—C3529.3 (4)
C15—O1—C14—O22.1 (4)C24—N27—C34—C35−175.7 (2)
C15—O1—C14—C10175.0 (3)C26—N27—C34—C39−151.7 (3)
N1—C10—C14—O2−159.7 (2)C24—N27—C34—C393.3 (4)
C9—C10—C14—O279.2 (3)C39—C34—C35—C360.7 (4)
C11—C10—C14—O2−43.1 (3)N27—C34—C35—C36179.7 (3)
N1—C10—C14—O127.3 (3)C34—C35—C36—C37−0.6 (5)
C9—C10—C14—O1−93.8 (2)C35—C36—C37—O6−179.9 (3)
C11—C10—C14—O1143.9 (2)C35—C36—C37—C380.3 (4)
C14—O1—C15—C16103.2 (5)C40—O6—C37—C363.4 (4)
C12—C11—C17—C22−30.5 (3)C40—O6—C37—C38−176.7 (2)
C10—C11—C17—C2289.3 (3)C36—C37—C38—C39−0.2 (4)
C12—C11—C17—C18148.4 (2)O6—C37—C38—C39179.9 (2)
C10—C11—C17—C18−91.8 (2)C37—C38—C39—C340.4 (4)
C22—C17—C18—C19−1.2 (3)C35—C34—C39—C38−0.6 (4)
C11—C17—C18—C19179.8 (2)N27—C34—C39—C38−179.6 (2)
C17—C18—C19—C200.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2A···N270.972.533.196 (3)126
C24—H24···O30.982.583.186 (3)121
C25—H25···O6i0.982.603.479 (3)150
C35—H35···O50.932.603.157 (3)119
C40—H40A···O4i0.962.493.232 (4)134

Symmetry codes: (i) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2676).

References

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