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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Feb 4;68(Pt 3):o587. doi: 10.1107/S1600536812002334

(1S,2S,6R,7aR)-2-Benzyl-1,6-dihy­droxy­hexa­hydro­pyrrolizin-3-one

F L Oliveira a, K R L Freire b, R Aparicio a,*, F Coelho b
PMCID: PMC3297313  PMID: 22412503

Abstract

In the title compound, C14H17NO3, the dihedral angles show that the H atoms at two stereocenters are in a trans-diaxial configuration. In the crystal, the molecules are linked by O—H⋯O hydrogen bonds. The absolute configuration of the molecule has been established on the basis of refinement of the Hooft and Flack parameters.

Related literature  

For a synthetic sequence for the preparation of the title compound, see: de Luna Freire et al. (2011 ▶). For the use of this type of compounds as LFA-1 (Lymphocyte Function-Associated Anti­gen-1) inhibitors, see: Baumann (2007 ▶). For a related structure, see: Newton et al. (2004 ▶).graphic file with name e-68-0o587-scheme1.jpg

Experimental  

Crystal data  

  • C14H17NO3

  • M r = 247.29

  • Orthorhombic, Inline graphic

  • a = 6.6241 (3) Å

  • b = 13.6873 (6) Å

  • c = 13.9726 (6) Å

  • V = 1266.84 (10) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.74 mm−1

  • T = 100 K

  • 0.17 × 0.15 × 0.12 mm

Data collection  

  • Bruker Kappa APEXII DUO diffractometer

  • 26923 measured reflections

  • 2295 independent reflections

  • 2290 reflections with I > 2σ(I)

  • R int = 0.026

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.026

  • wR(F 2) = 0.078

  • S = 1.15

  • 2295 reflections

  • 172 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.16 e Å−3

  • Absolute structure: Flack (1983 ▶) and Hooft et al. (2008 ▶) [Hooft parameter = 0.00(2), (943 Bijvoet pairs)]

  • Flack parameter: 0.00 (16)

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010) ▶ and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002334/pv2494sup1.cif

e-68-0o587-sup1.cif (22.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002334/pv2494Isup2.hkl

e-68-0o587-Isup2.hkl (112.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812002334/pv2494Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3A⋯O2i 0.93 (2) 1.73 (2) 2.6395 (12) 164 (2)
O1—H1A⋯O3ii 0.86 (2) 1.93 (2) 2.7716 (13) 167 (19)
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Acknowledgments

The authors acknowledge the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), the Coorden­ação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial support. FLO and KRLF were supported by fellowships from CAPES and CNPq, respectively. RA and FC are recipients of research fellowships from CNPq.

supplementary crystallographic information

Comment

The title compound can be used as a prototype for the development of new inhibitors of LFA-1 (lymphocyte function-associated antigen 1) with potential application as anti-inflammatory agents (Baumann, 2007). The title compound is a new asymmetric benzyl-pyrrolizidinone which has been synthesized in our laboratory and its crystal structure is presented in this article.

The title compound (Fig. 1) has four stereocenters and was prepared from a Morita-Baylis-Hillman adduct. The dihedral angles H3—C3—C4—H4 = -158° and H4—C4—C5—H5 = 163° show that H atoms 3, 4 and 5 at the two new stereocenters are in a trans-diaxial configuration. These values agree with the coupling constant values obtained for these H atoms in the 1H NMR analysis. The crystal structure is stabilized by intermolecular hydrogen bonds (Tab. 1 & Fig. 2).

Experimental

The title compound was prepared using a synthetic sequence described in the literature (de Luna Freire et al., 2011) and purified by flash silica gel column chromatography (CH2Cl2:MeOH – solvent gradient: 0:100 to 97:03) to afford 0.06 g (as a white solid) in 97% yield. It was then recrystallized using the liquid-vapor saturation method, dissolved in ethanol and crystallized with a vapor pressure of a second less polar liquid (ethyl ether), in a closed camera, providing the slow formation of crystals.

Refinement

The H-atoms bonded to C-atoms were included in the refinements at geometrically idealized positions with C—H = 0.95, 0.99 and 1.00 Å, for aryl, methylene and methyne H-atoms, respectively, with and Uiso(H) = 1.2 times Ueq(C). The H-atoms bonded to O atoms were allowed to refine freely. The Flack parameter was x=0.00 (16) (Flack, 1983). Further analysis of the absolute structure was performed using likelihood methods (Hooft et al., 2008) with PLATON (Spek, 2009). A total of 943 Bijvoet pairs were included in the calculations. The resulting value of the Hooft parameter was y = 0.00 (2), with a probability for an inverted structure smaller than 1x10-100. These results indicated that the absolute structure has been correctly assigned.

Figures

Fig. 1.

Fig. 1.

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Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

Fig. 2.

Fig. 2.

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A unit cell packing diagram of the title compound showing hydrogen bonds as dashed lines.

Crystal data

C14H17NO3 Dx = 1.297 Mg m−3
Mr = 247.29 Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121 Cell parameters from 2295 reflections
a = 6.6241 (3) Å θ = 4.5–69.5°
b = 13.6873 (6) Å µ = 0.74 mm−1
c = 13.9726 (6) Å T = 100 K
V = 1266.84 (10) Å3 Rectangular, colourless
Z = 4 0.17 × 0.15 × 0.12 mm
F(000) = 528
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Data collection

Bruker Kappa APEXII DUO diffractometer 2290 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.026
Graphite monochromator θmax = 69.5°, θmin = 4.5°
Bruker APEX CCD area–detector scans h = −7→7
26923 measured reflections k = −15→16
2295 independent reflections l = −16→16
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Refinement

Refinement on F2 Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.026 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.1808P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078 (Δ/σ)max = 0.001
S = 1.15 Δρmax = 0.17 e Å−3
2295 reflections Δρmin = −0.16 e Å−3
172 parameters Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints Extinction coefficient: 0.0086 (8)
Primary atom site location: structure-invariant direct methods Absolute structure: Flack (1983) and Hooft et al. (2008) [Hooft parameter = 0.00(2), (943 Bijvoet pairs)]'
Secondary atom site location: difference Fourier map Flack parameter: 0.00 (16)
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Special details

Experimental. [α]D20 + 51 (c 1, MeOH); M. p. 135–136° C; IR (KBr, vmax): 3404, 3232, 2987, 2936, 2897, 2871, 1670, 1447, 1416, 1375, 1300, 1263, 1222,1175, 1121 cm-1; 1H NMR (500 MHz, CD3OD) δ 1.55 (dddd, J = 13.4, 5.3, 4.0, 1.0 Hz, 1H, H-2 A); 2.25 (ddd, J = 13.4, 8.0, 5.4 Hz, 1H, H-2B); 2.93 (m, 2H, H-8, H-5); 3.02 (m, J = 7.5, 1.8 Hz, 1H, H-6); 3.08 (ddd, J = 12.0, 4.9, 1.3 Hz, 1H, H-14 A); 3.52 (dd, J = 12.0, 2.4 Hz, 1H, H-14B); 3.64 (m, JH3,H4 = 7.0, J = 8.0, 5.3 Hz, 1H, H-3); 3.88 (dd,JH4,H5 = 9.4, JH3,H4 = 7.0 Hz, 1H, H-4); 4.41 (m, J = 5.1, 4.0, 3.0 Hz, 1H, H-1); 7.15 (m, 1H, H—Ar); 7.23 (m, 2H, H—Ar); 7.29 (m, 2H, H—Ar); 13C NMR (62.5 MHz, (CD3)2CO) δ 34.4, 38.6, 52.3, 54.0, 65.6, 72.4, 80.6, 126.5, 128.7, 130.3, 141.0, 175.6; HRMS (ESI-TOF) Calcd. for C14H18NO3 [M + H]+ 248.1287. Found 248.1286.
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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.38278 (15) 0.66691 (6) 0.06882 (7) 0.0253 (2)
O2 −0.07013 (13) 0.91601 (7) 0.27608 (7) 0.0264 (2)
O3 0.61142 (13) 1.03167 (6) 0.28357 (7) 0.0238 (2)
N1 0.21491 (16) 0.88149 (7) 0.19167 (7) 0.0204 (3)
C1 0.3664 (2) 0.76715 (9) 0.09195 (9) 0.0217 (3)
H1 0.3789 0.8046 0.0308 0.026*
C2 0.52450 (19) 0.80862 (9) 0.16169 (9) 0.0216 (3)
H2A 0.5399 0.7667 0.2189 0.026*
H2B 0.6575 0.8168 0.1304 0.026*
C3 0.42952 (18) 0.90724 (9) 0.18696 (9) 0.0193 (3)
H3 0.4529 0.9549 0.1338 0.023*
C4 0.46008 (18) 0.95809 (9) 0.28423 (9) 0.0192 (3)
H4 0.4913 0.9084 0.3346 0.023*
C5 0.25242 (19) 1.00357 (9) 0.30318 (9) 0.0200 (3)
H5 0.2442 1.0650 0.2646 0.024*
C6 0.20002 (19) 1.03016 (9) 0.40713 (9) 0.0235 (3)
H6A 0.2759 1.0898 0.4249 0.028*
H6B 0.0544 1.0461 0.4105 0.028*
C7 0.2453 (2) 0.95143 (9) 0.48012 (9) 0.0256 (3)
C8 0.1026 (3) 0.87967 (10) 0.50128 (10) 0.0335 (3)
H8 −0.0244 0.8801 0.4697 0.040*
C9 0.1451 (3) 0.80737 (11) 0.56844 (10) 0.0428 (4)
H9 0.0466 0.7591 0.5826 0.051*
C10 0.3288 (3) 0.80545 (11) 0.61435 (10) 0.0421 (4)
H10 0.3573 0.7556 0.6597 0.050*
C11 0.10960 (19) 0.92968 (8) 0.25733 (9) 0.0210 (3)
C12 0.4306 (2) 0.94914 (10) 0.52735 (9) 0.0288 (3)
H12 0.5291 0.9976 0.5137 0.035*
C13 0.4730 (3) 0.87670 (11) 0.59435 (10) 0.0372 (4)
H13 0.5996 0.8759 0.6263 0.045*
C14 0.1616 (2) 0.79469 (9) 0.13686 (9) 0.0235 (3)
H14A 0.0595 0.8096 0.0872 0.028*
H14B 0.1101 0.7420 0.1788 0.028*
H3A 0.737 (4) 1.0009 (16) 0.2841 (14) 0.050 (5)*
H1A 0.379 (3) 0.6326 (15) 0.1204 (16) 0.043 (5)*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0350 (5) 0.0173 (4) 0.0237 (4) 0.0039 (4) 0.0009 (4) −0.0011 (3)
O2 0.0173 (4) 0.0252 (4) 0.0368 (5) 0.0013 (4) 0.0018 (4) −0.0020 (4)
O3 0.0171 (4) 0.0209 (4) 0.0334 (5) −0.0010 (4) 0.0019 (4) −0.0044 (4)
N1 0.0183 (5) 0.0200 (5) 0.0229 (5) 0.0017 (4) −0.0018 (4) −0.0007 (4)
C1 0.0283 (7) 0.0173 (6) 0.0194 (6) 0.0033 (5) −0.0009 (5) 0.0005 (5)
C2 0.0212 (6) 0.0210 (6) 0.0226 (6) 0.0038 (5) 0.0022 (5) −0.0001 (5)
C3 0.0181 (6) 0.0189 (5) 0.0209 (6) 0.0020 (5) 0.0013 (4) 0.0018 (5)
C4 0.0185 (6) 0.0166 (5) 0.0226 (6) 0.0008 (4) 0.0018 (4) −0.0003 (5)
C5 0.0188 (6) 0.0162 (5) 0.0251 (6) 0.0022 (4) 0.0024 (5) 0.0008 (5)
C6 0.0225 (6) 0.0196 (6) 0.0283 (6) 0.0001 (5) 0.0056 (5) −0.0049 (5)
C7 0.0351 (7) 0.0200 (6) 0.0217 (6) 0.0004 (5) 0.0089 (5) −0.0059 (5)
C8 0.0473 (9) 0.0292 (7) 0.0242 (6) −0.0096 (6) 0.0082 (6) −0.0073 (5)
C9 0.0763 (13) 0.0275 (7) 0.0245 (7) −0.0166 (8) 0.0113 (8) −0.0040 (6)
C10 0.0797 (13) 0.0242 (7) 0.0223 (7) 0.0054 (8) 0.0092 (8) −0.0007 (5)
C11 0.0203 (6) 0.0182 (5) 0.0246 (6) 0.0039 (5) −0.0010 (5) 0.0023 (5)
C12 0.0342 (7) 0.0259 (6) 0.0263 (6) 0.0032 (6) 0.0067 (5) −0.0017 (5)
C13 0.0522 (10) 0.0351 (8) 0.0244 (7) 0.0117 (7) 0.0047 (7) −0.0030 (6)
C14 0.0238 (6) 0.0227 (6) 0.0240 (6) 0.0009 (5) −0.0033 (5) −0.0035 (5)
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Geometric parameters (Å, º)

O1—C1 1.4138 (15) C5—C6 1.5371 (16)
O1—H1A 0.86 (2) C5—H5 1.0000
O2—C11 1.2333 (16) C6—C7 1.5138 (18)
O3—C4 1.4210 (14) C6—H6A 0.9900
O3—H3A 0.93 (2) C6—H6B 0.9900
N1—C11 1.3279 (17) C7—C12 1.394 (2)
N1—C14 1.4571 (16) C7—C8 1.395 (2)
N1—C3 1.4661 (16) C8—C9 1.392 (2)
C1—C2 1.5390 (18) C8—H8 0.9500
C1—C14 1.5417 (18) C9—C10 1.376 (3)
C1—H1 1.0000 C9—H9 0.9500
C2—C3 1.5306 (16) C10—C13 1.393 (3)
C2—H2A 0.9900 C10—H10 0.9500
C2—H2B 0.9900 C12—C13 1.392 (2)
C3—C4 1.5403 (16) C12—H12 0.9500
C3—H3 1.0000 C13—H13 0.9500
C4—C5 1.5328 (17) C14—H14A 0.9900
C4—H4 1.0000 C14—H14B 0.9900
C5—C11 1.5258 (17)
C1—O1—H1A 109.6 (14) C6—C5—H5 107.3
C4—O3—H3A 107.9 (14) C7—C6—C5 115.04 (10)
C11—N1—C14 129.85 (11) C7—C6—H6A 108.5
C11—N1—C3 114.90 (10) C5—C6—H6A 108.5
C14—N1—C3 114.06 (10) C7—C6—H6B 108.5
O1—C1—C2 116.78 (11) C5—C6—H6B 108.5
O1—C1—C14 113.45 (11) H6A—C6—H6B 107.5
C2—C1—C14 104.54 (10) C12—C7—C8 118.72 (13)
O1—C1—H1 107.2 C12—C7—C6 120.64 (12)
C2—C1—H1 107.2 C8—C7—C6 120.64 (14)
C14—C1—H1 107.2 C9—C8—C7 120.42 (16)
C3—C2—C1 101.05 (10) C9—C8—H8 119.8
C3—C2—H2A 111.6 C7—C8—H8 119.8
C1—C2—H2A 111.6 C10—C9—C8 120.42 (15)
C3—C2—H2B 111.6 C10—C9—H9 119.8
C1—C2—H2B 111.6 C8—C9—H9 119.8
H2A—C2—H2B 109.4 C9—C10—C13 119.97 (15)
N1—C3—C2 101.36 (10) C9—C10—H10 120.0
N1—C3—C4 101.33 (9) C13—C10—H10 120.0
C2—C3—C4 123.23 (10) O2—C11—N1 125.35 (12)
N1—C3—H3 109.9 O2—C11—C5 127.58 (11)
C2—C3—H3 109.9 N1—C11—C5 107.07 (11)
C4—C3—H3 109.9 C13—C12—C7 120.81 (14)
O3—C4—C5 110.27 (9) C13—C12—H12 119.6
O3—C4—C3 114.03 (10) C7—C12—H12 119.6
C5—C4—C3 102.59 (10) C12—C13—C10 119.65 (16)
O3—C4—H4 109.9 C12—C13—H13 120.2
C5—C4—H4 109.9 C10—C13—H13 120.2
C3—C4—H4 109.9 N1—C14—C1 101.53 (10)
C11—C5—C4 102.40 (9) N1—C14—H14A 111.5
C11—C5—C6 114.43 (10) C1—C14—H14A 111.5
C4—C5—C6 117.51 (10) N1—C14—H14B 111.5
C11—C5—H5 107.3 C1—C14—H14B 111.5
C4—C5—H5 107.3 H14A—C14—H14B 109.3
C(11)—N(1)—C(3)—C(2) 145.23 (10) H(1)—C(1)—C(2)—C(3) 73
C(11)—N(1)—C(3)—C(4) 17.61 (13) H(1)—C(1)—C(2)—H(2A) −169
C(14)—N(1)—C(3)—C(2) −23.51 (13) H(1)—C(1)—C(2)—H(2B) −46
C(14)—N(1)—C(3)—C(4) −151.12 (10) O(1)—C(1)—C(14)—H(14A) −86
C(3)—N(1)—C(11)—O(2) −176.49 (12) O(1)—C(1)—C(14)—H(14B) 36
C(3)—N(1)—C(11)—C(5) 3.73 (13) C(2)—C(1)—C(14)—H(14A) 145
C(14)—N(1)—C(11)—O(2) −9.9 (2) C(2)—C(1)—C(14)—H(14B) −92
C(14)—N(1)—C(11)—C(5) 170.29 (11) H(1)—C(1)—C(14)—N(1) −87
C(3)—N(1)—C(14)—C(1) −1.76 (13) H(1)—C(1)—C(14)—H(14A) 32
C(11)—N(1)—C(14)—C(1) −168.41 (12) H(1)—C(1)—C(14)—H(14B) 154
O(1)—C(1)—C(2)—C(3) −167.02 (10) C(1)—C(2)—C(3)—H(3) −78
C(14)—C(1)—C(2)—C(3) −40.78 (12) H(2A)—C(2)—C(3)—N(1) −81
O(1)—C(1)—C(14)—N(1) 154.80 (10) H(2A)—C(2)—C(3)—C(4) 31
C(2)—C(1)—C(14)—N(1) 26.51 (12) H(2A)—C(2)—C(3)—H(3) 163
C(1)—C(2)—C(3)—N(1) 38.05 (11) H(2B)—C(2)—C(3)—N(1) 157
C(1)—C(2)—C(3)—C(4) 149.83 (11) H(2B)—C(2)—C(3)—C(4) −91
N(1)—C(3)—C(4)—O(3) −149.89 (9) H(2B)—C(2)—C(3)—H(3) 41
N(1)—C(3)—C(4)—C(5) −30.67 (11) N(1)—C(3)—C(4)—H(4) 86
C(2)—C(3)—C(4)—O(3) 98.31 (13) C(2)—C(3)—C(4)—H(4) −26
C(2)—C(3)—C(4)—C(5) −142.47 (11) H(3)—C(3)—C(4)—O(3) −34
O(3)—C(4)—C(5)—C(6) −78.74 (13) H(3)—C(3)—C(4)—C(5) 86
O(3)—C(4)—C(5)—C(11) 154.95 (10) H(3)—C(3)—C(4)—H(4) −158
C(3)—C(4)—C(5)—C(6) 159.44 (10) O(3)—C(4)—C(5)—H(5) 42
C(3)—C(4)—C(5)—C(11) 33.13 (12) C(3)—C(4)—C(5)—H(5) −80
C(4)—C(5)—C(6)—C(7) −47.18 (15) H(4)—C(4)—C(5)—C(6) 43
C(11)—C(5)—C(6)—C(7) 72.99 (14) H(4)—C(4)—C(5)—C(11) −84
C(4)—C(5)—C(11)—O(2) 156.61 (12) H(4)—C(4)—C(5)—H(5) 163
C(4)—C(5)—C(11)—N(1) −23.61 (12) C(4)—C(5)—C(6)—H(6A) 75
C(6)—C(5)—C(11)—O(2) 28.33 (18) C(4)—C(5)—C(6)—H(6B) −169
C(6)—C(5)—C(11)—N(1) −151.89 (10) C(11)—C(5)—C(6)—H(6A) −165
C(5)—C(6)—C(7)—C(8) −87.85 (15) C(11)—C(5)—C(6)—H(6B) −49
C(5)—C(6)—C(7)—C(12) 92.02 (14) H(5)—C(5)—C(6)—C(7) −168
C(6)—C(7)—C(8)—C(9) 179.96 (13) H(5)—C(5)—C(6)—H(6A) −46
C(12)—C(7)—C(8)—C(9) 0.1 (2) H(5)—C(5)—C(6)—H(6B) 70
C(6)—C(7)—C(12)—C(13) −179.84 (12) H(5)—C(5)—C(11)—O(2) −91
C(8)—C(7)—C(12)—C(13) 0.0 (2) H(5)—C(5)—C(11)—N(1) 89
C(7)—C(8)—C(9)—C(10) −0.4 (2) H(6A)—C(6)—C(7)—C(8) 150
C(8)—C(9)—C(10)—C(13) 0.6 (2) H(6A)—C(6)—C(7)—C(12) −30
C(9)—C(10)—C(13)—C(12) −0.5 (2) H(6B)—C(6)—C(7)—C(8) 34
C(7)—C(12)—C(13)—C(10) 0.2 (2) H(6B)—C(6)—C(7)—C(12) −146
H(1A)—O(1)—C(1)—C(2) 56.8 (14) C(6)—C(7)—C(8)—H(8) 0
H(1A)—O(1)—C(1)—C(14) −64.9 (14) C(12)—C(7)—C(8)—H(8) −180
H(1A)—O(1)—C(1)—H(1) 177 C(6)—C(7)—C(12)—H(12) 0
H(3A)—O(3)—C(4)—C(3) −76.3 (13) C(8)—C(7)—C(12)—H(12) −180
H(3A)—O(3)—C(4)—C(5) 168.9 (13) C(7)—C(8)—C(9)—H(9) 180
H(3A)—O(3)—C(4)—H(4) 48 H(8)—C(8)—C(9)—C(10) 180
C(11)—N(1)—C(3)—H(3) −99 H(8)—C(8)—C(9)—H(9) 0
C(14)—N(1)—C(3)—H(3) 93 C(8)—C(9)—C(10)—H(10) −179
C(3)—N(1)—C(14)—H(14A) −121 H(9)—C(9)—C(10)—C(13) −179
C(3)—N(1)—C(14)—H(14B) 117 H(9)—C(9)—C(10)—H(10) 1
C(11)—N(1)—C(14)—H(14A) 73 C(9)—C(10)—C(13)—H(13) 179
C(11)—N(1)—C(14)—H(14B) −50 H(10)—C(10)—C(13)—C(12) 180
O(1)—C(1)—C(2)—H(2A) −48 H(10)—C(10)—C(13)—H(13) 0
O(1)—C(1)—C(2)—H(2B) 74 C(7)—C(12)—C(13)—H(13) −180
C(14)—C(1)—C(2)—H(2A) 78 H(12)—C(12)—C(13)—C(10) −180
C(14)—C(1)—C(2)—H(2B) −159 H(12)—C(12)—C(13)—H(13) 0
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O3—H3A···O2i 0.93 (2) 1.73 (2) 2.6395 (12) 164 (2)
O1—H1A···O3ii 0.86 (2) 1.93 (2) 2.7716 (13) 167 (19)
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Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2494).

References

  1. Baumann, K. O. (2007). WO Patent 2007039286; Chem Abstr. 146, 421836.
  2. Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  4. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  5. Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96–103. [DOI] [PMC free article] [PubMed]
  6. Luna Freire, K. R. de, Tormena, C. F. & Coelho, F. (2011). Synlett, 14, 2059–2063.
  7. Newton, C., Ameijde, J., Fleet, G. W. J., Nash, R. J. & Watkin, D. J. (2004). Acta Cryst. E60, o1463–o1464.
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  9. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  10. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002334/pv2494sup1.cif

e-68-0o587-sup1.cif (22.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002334/pv2494Isup2.hkl

e-68-0o587-Isup2.hkl (112.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812002334/pv2494Isup3.cml

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

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

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