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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages o3233-o3234

1,3-Di­cyclo­hexyl­imidazolidine-2,4,5-trione: a second polymorph

aDepartment of Chemistry, University of Aveiro, QOPNA, 3810-193 Aveiro, Portugal, and bDepartment of Chemistry, University of Aveiro, CICECO, 3810-193 Aveiro, Portugal
*Correspondence e-mail: artur.silva@ua.pt, filipe.paz@ua.pt

(Received 28 September 2012; accepted 21 October 2012; online 27 October 2012)

The title compound, C15H22N2O3, was obtained as a by-product of oxidative cleavage of 1,3-dicyclo­hexyl-(3-oxo-2,3-dihydro­benzofuran-2-yl)imidazolidine-2,4-dione. Herein, we report the crystal structure of a second polymorph, which was obtained by crystallization from an ethanol solution at 253 K, instead of slow evaporation of the same solvent at room temperature. While the first polymorph [Talhi et al. (2011). Acta Cryst. E67, o3243] crystallized in the non-centrosymmetric space group P212121, this second polymorph crystallizes in the centrosymmetric space group P21/n. Compared to the first polymorph, in the crystal no C=O⋯C=O inter­actions were found (C⋯O inter­molecular distance longer than 3.15 Å) and instead, close packing of individual mol­ecular units is mediated by C—H⋯π and weak C—H⋯O inter­actions.

Related literature

For the structure of the ortho­rhom­bic polymorph and further background information to the study, see: Talhi et al. (2011[Talhi, O., Fernandes, J. A., Pinto, D. C. G. A., Silva, A. M. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o3243.]). For general background on crystallographic studies by our research group of related compounds having biological activity, see: Fernandes et al. (2011[Fernandes, J. A., Almeida Paz, F. A., Marques, J., Marques, M. P. M. & Braga, S. S. (2011). Acta Cryst. C67, o57-o59.]); Loughzail et al. (2011[Loughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075-o2076.]). For determination of the melting point, see: Ulrichan & Sayigh (1965[Ulrichan, H. & Sayigh, D. A. A. R. (1965). J. Org. Chem. 30, 2781-2783.]).

[Scheme 1]

Experimental

Crystal data
  • C15H22N2O3

  • Mr = 278.35

  • Monoclinic, P 21 /n

  • a = 5.1980 (2) Å

  • b = 21.7123 (10) Å

  • c = 13.0244 (6) Å

  • β = 100.163 (2)°

  • V = 1446.88 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 150 K

  • 0.13 × 0.06 × 0.06 mm

Data collection
  • Bruker X8 Kappa CCD APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.]) Tmin = 0.989, Tmax = 0.995

  • 38115 measured reflections

  • 3876 independent reflections

  • 2999 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.104

  • S = 1.04

  • 3876 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Short intermolecular interactions (Å, °)

Cg is the centroid of the N1/N2/C1–C3 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7BCgi 0.99 2.78 3.5511 (14) 135
C11—H11B⋯O2ii 0.99 2.51 3.2065 (18) 127
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2005[Bruker (2005). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus (Bruker, 2005[Bruker (2005). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

In a previous publication (Talhi et al., 2011) we described the crystal structure (polymorph I) of 1,3-dicyclohexylparabanic acid (see chemical diagram and Figure 1) obtained as a by-product of the oxidative cleavage of the C2'-C5 single bond of 1,3-dicyclohexyl-(3-oxo-2,3-dihydrobenzofuran-2-yl)imidazolidine-2,4-dione, using catalytic I2/DMSO system at 463 K. Following our interest on the structural features of compounds having biological activity (Fernandes et al., 2011; Loughzail et al. 2011; Talhi et al., 2011), particularly in our quest for novel polymorphic forms of pharmaceutic products, we wish to report the structure of a second crystalline polymorph of the title compound (polymorph II) obtained when applying a different crystallization procedure from that previously reported by us: while polymorph I was obtained by slow evaporation of an ethanolic solution at room temperature, polymorph II was obtained instead by cooling overnight the same solution at 253 K.

The asymmetric unit comprises a whole molecular unit of the title compound, C15H22N2O3 (Scheme and Figure 1). The central parabanic acid residue and the attached carbon atoms are coplanar with the largest deviation from the medium plane being 0.075 (1) Å for C4. The two cyclohexyl substituent groups appear exhibiting the chair typical conformation and their medium planes subtend slightly different angles with the aforementioned central plane, being one almost perpendicular [88.73 (5)°] and the other of 74.15 (6)°. We note that the observed angles for these two planes are larger than those registered for polymorph I in which the analogous values are ca 81 and 87° (Talhi et al., 2011). Remarkably the four possible N—C—C—C groups involving three adjacent carbon atoms of the cyclohexyl moieties are also very near the planarity [largest deviation of 0.019 (1) Å for C10 in N1—C10—C11—C12].

The crystal packing is mainly governed by the need to fill the available space. A handful of weak supramolecular interactions are also observed, namely C—H···π and C—H···O (See Table 1 and Figure 2). While in the crystal structure of polymorph I a strong CO···CO interaction with a C···O distance smaller than 2.871 Å was observed, in the present polymorph II the shortest C···O intermolecular distance is 3.1519 (15) Å, which, in comparison to the case of polymorph I, may be considered as negligible.

Related literature top

For the structure of the orthorhombic polymorph and further background information to the study, see: Talhi et al. (2011). For general background on crystallographic studies by our research group of related compounds having biological activity, see: Fernandes et al. (2011); Loughzail et al. (2011). For related literature [on what subject?], see: Bernadou & Meunier (2004); For determination of the melting point, see: Ulrichan & Sayigh (1965).

Experimental top

The title compound was prepared following the procedure described previously (Talhi et al., 2011), except for the crystallization process in which the raw compound was dissolved in ethanol and crystallized at 253 K overnight.

The melting point was measured on a Buchi B-540 equipment. NMR spectra were recorded on a Bruker Avance 300 spectrometer (300.13 for 1H and 75.47 MHz for 13C), with CDCl3 used as solvent. Chemical shifts (δ) are reported in p.p.m. and coupling constants (J) in Hz. The internal standard was TMS.

Unequivocal 13C assignments have been performed with the aid of bidimensional experiments (HSQC and HMBC). Both 1H and 13C NMR spectra show bilateral symmetry of the compound in solution. The HSQC spectrum allowed to deduce the electronegative effect of the nitrogen atom on the cyclohexyl proton and carbon resonances. However, it was found that the anisotropic effects of the carbonyl groups influence greatly the chemical shift values of the cyclohexyl proton resonances. Both of the highlighted effects of the parabanic nucleus heteroatoms are spread throughout the cyclohexyl chair skeleton decreasing gradually from C-1' to C-4'. Important features are recorded in the HMBC experiment concerning the carbon neighboring of the tertiary proton H-1' which correlates with the carbonyl groups C-2 and C-5, and further with C-2' and C-3' of the cyclohexyl radical.

Elemental Analysis: Calculated (in %): C, 64.73; H, 7.97; N, 10.06; Found: C, 64.47; H, 7.96; N, 10.05.

Melting point: 175 °C (Lit [Ulrichan & Sayigh, 1965] 174–175 °C).

HRMS(ESI+): m/z Calcd for [C15H22N2O3 + Na]+: 301.1528; found 301.1523.

1H NMR (300.13 MHz, CDCl3): δ = 1.14–1.26 and 1.63–1.71 (2 m, 4 H, H-4'), 1.26–1.43 and 1.80–1.91 (2 m, 4 H, H-3'), 1.73–1.77 and 1.97–2.19 (2 m, 4 H, H-2'), 4.00 (tt, J= 12.0 and 3.7 Hz, 2 H, H-1') p.p.m..

13C NMR (75.47 MHz, CDCl3): δ = 24.7 (C-4'), 25.6 (C-3'), 29.5 (C-2'), 52.4 (C-1'), 153.4 (C-2), 156.4 (C-4,5) p.p.m..

Refinement top

Hydrogen atoms bound to carbon were placed in idealized positions with C—H = 1.00 (for the tertiary carbons) and 0.99 Å (for the —CH2— moieties). These atoms were included in the final structural model in riding-motion approximation with the isotropic thermal displacement parameters fixed at 1.2×Ueq of the carbon atom to which they are attached.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Schematic representation of the asymmetric unit of the title compound which comprises a whole molecule. Non-hydrogen atoms are represented as thermal ellipsoids drawn at the 70% probability level and hydrogen atoms as small spheres with arbitrary radii.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the [100] direction of the unit cell. C—H···π interactions are represented as dashed green lines, and C—H···O weak hydrogen bonding interactions are represented as dashed pink lines. See Table 1 for geometrical details on the represented supramolecular interactions.
1,3-Dicyclohexylimidazolidine-2,4,5-trione top
Crystal data top
C15H22N2O3F(000) = 600
Mr = 278.35Dx = 1.278 Mg m3
Monoclinic, P21/nMelting point: 175 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 5.1980 (2) ÅCell parameters from 3876 reflections
b = 21.7123 (10) Åθ = 3.7–29.1°
c = 13.0244 (6) ŵ = 0.09 mm1
β = 100.163 (2)°T = 150 K
V = 1446.88 (11) Å3Block, yellow
Z = 40.13 × 0.06 × 0.06 mm
Data collection top
Bruker X8 Kappa CCD APEXII
diffractometer
3876 independent reflections
Radiation source: fine-focus sealed tube2999 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω and ϕ scansθmax = 29.1°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 67
Tmin = 0.989, Tmax = 0.995k = 2929
38115 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0374P)2 + 0.6588P]
where P = (Fo2 + 2Fc2)/3
3876 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C15H22N2O3V = 1446.88 (11) Å3
Mr = 278.35Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.1980 (2) ŵ = 0.09 mm1
b = 21.7123 (10) ÅT = 150 K
c = 13.0244 (6) Å0.13 × 0.06 × 0.06 mm
β = 100.163 (2)°
Data collection top
Bruker X8 Kappa CCD APEXII
diffractometer
3876 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
2999 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.995Rint = 0.049
38115 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å3
3876 reflectionsΔρmin = 0.18 e Å3
181 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.9734 (2)0.59882 (5)0.12018 (9)0.0179 (2)
C20.7011 (2)0.59707 (6)0.23971 (10)0.0187 (2)
C30.6479 (2)0.65531 (6)0.17166 (10)0.0189 (2)
C40.8265 (2)0.69411 (5)0.01391 (9)0.0182 (2)
H40.96410.67880.02450.022*
C50.9020 (3)0.75914 (6)0.05202 (10)0.0225 (3)
H5A1.07630.75850.09730.027*
H5B0.77400.77480.09370.027*
C60.9077 (3)0.80176 (6)0.04117 (11)0.0246 (3)
H6A0.94800.84420.01570.030*
H6B1.04820.78830.07850.030*
C70.6476 (3)0.80154 (6)0.11652 (10)0.0224 (3)
H7A0.50980.81900.08150.027*
H7B0.66130.82780.17750.027*
C80.5724 (3)0.73639 (6)0.15326 (10)0.0255 (3)
H8A0.70010.72080.19510.031*
H8B0.39820.73710.19860.031*
C90.5654 (3)0.69293 (6)0.06145 (10)0.0235 (3)
H9A0.42360.70560.02420.028*
H9B0.52820.65050.08770.028*
C101.0256 (2)0.50852 (5)0.24346 (10)0.0185 (2)
H101.19260.50480.21580.022*
C111.0949 (3)0.50699 (6)0.36255 (10)0.0227 (3)
H11A0.93390.51070.39290.027*
H11B1.21050.54210.38760.027*
C121.2335 (3)0.44639 (6)0.39731 (11)0.0257 (3)
H12A1.40080.44430.37110.031*
H12B1.27330.44480.47440.031*
C131.0635 (3)0.39147 (6)0.35622 (13)0.0334 (3)
H13A0.90260.39160.38710.040*
H13B1.15930.35280.37730.040*
C140.9900 (3)0.39390 (6)0.23745 (13)0.0351 (4)
H14A0.87320.35890.21290.042*
H14B1.14990.38970.20650.042*
C150.8525 (3)0.45432 (6)0.20050 (11)0.0263 (3)
H15A0.81760.45580.12330.032*
H15B0.68320.45690.22510.032*
N10.9031 (2)0.56747 (5)0.20531 (8)0.0185 (2)
N20.8172 (2)0.65170 (5)0.10196 (8)0.0182 (2)
O11.13883 (18)0.58316 (4)0.07174 (7)0.0244 (2)
O20.58424 (18)0.58220 (4)0.30792 (7)0.0260 (2)
O30.49016 (18)0.69488 (4)0.18021 (8)0.0259 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0198 (6)0.0174 (5)0.0157 (6)0.0008 (4)0.0015 (5)0.0002 (4)
C20.0183 (6)0.0194 (5)0.0182 (6)0.0008 (4)0.0023 (5)0.0007 (4)
C30.0186 (6)0.0201 (6)0.0178 (6)0.0009 (5)0.0025 (5)0.0005 (5)
C40.0201 (6)0.0183 (5)0.0160 (6)0.0007 (4)0.0031 (5)0.0049 (4)
C50.0232 (7)0.0206 (6)0.0215 (6)0.0030 (5)0.0022 (5)0.0030 (5)
C60.0228 (7)0.0216 (6)0.0283 (7)0.0030 (5)0.0012 (5)0.0060 (5)
C70.0218 (6)0.0223 (6)0.0227 (6)0.0025 (5)0.0030 (5)0.0060 (5)
C80.0282 (7)0.0262 (6)0.0198 (6)0.0003 (5)0.0019 (5)0.0037 (5)
C90.0244 (7)0.0227 (6)0.0213 (6)0.0048 (5)0.0022 (5)0.0024 (5)
C100.0209 (6)0.0165 (5)0.0182 (6)0.0023 (4)0.0041 (5)0.0021 (4)
C110.0272 (7)0.0213 (6)0.0189 (6)0.0027 (5)0.0023 (5)0.0016 (5)
C120.0277 (7)0.0278 (6)0.0210 (6)0.0061 (5)0.0026 (5)0.0055 (5)
C130.0327 (8)0.0228 (7)0.0434 (9)0.0033 (6)0.0036 (7)0.0134 (6)
C140.0391 (8)0.0171 (6)0.0442 (9)0.0011 (6)0.0062 (7)0.0031 (6)
C150.0297 (7)0.0187 (6)0.0279 (7)0.0001 (5)0.0025 (6)0.0008 (5)
N10.0214 (5)0.0175 (5)0.0176 (5)0.0015 (4)0.0059 (4)0.0019 (4)
N20.0196 (5)0.0176 (5)0.0178 (5)0.0020 (4)0.0044 (4)0.0027 (4)
O10.0287 (5)0.0242 (4)0.0225 (5)0.0060 (4)0.0105 (4)0.0031 (4)
O20.0259 (5)0.0288 (5)0.0255 (5)0.0017 (4)0.0110 (4)0.0057 (4)
O30.0251 (5)0.0254 (5)0.0284 (5)0.0074 (4)0.0079 (4)0.0030 (4)
Geometric parameters (Å, º) top
C1—O11.2017 (15)C8—H8A0.9900
C1—N21.4022 (15)C8—H8B0.9900
C1—N11.4033 (15)C9—H9A0.9900
C2—O21.2052 (15)C9—H9B0.9900
C2—N11.3723 (16)C10—N11.4760 (15)
C2—C31.5409 (17)C10—C151.5262 (17)
C3—O31.2062 (15)C10—C111.5296 (17)
C3—N21.3734 (16)C10—H101.0000
C4—N21.4781 (15)C11—C121.5297 (18)
C4—C51.5250 (17)C11—H11A0.9900
C4—C91.5284 (18)C11—H11B0.9900
C4—H41.0000C12—C131.524 (2)
C5—C61.5307 (18)C12—H12A0.9900
C5—H5A0.9900C12—H12B0.9900
C5—H5B0.9900C13—C141.527 (2)
C6—C71.5239 (18)C13—H13A0.9900
C6—H6A0.9900C13—H13B0.9900
C6—H6B0.9900C14—C151.5302 (19)
C7—C81.5220 (18)C14—H14A0.9900
C7—H7A0.9900C14—H14B0.9900
C7—H7B0.9900C15—H15A0.9900
C8—C91.5288 (18)C15—H15B0.9900
O1—C1—N2126.12 (11)H9A—C9—H9B108.1
O1—C1—N1126.00 (11)N1—C10—C15110.74 (10)
N2—C1—N1107.88 (10)N1—C10—C11111.77 (10)
O2—C2—N1129.00 (12)C15—C10—C11111.92 (10)
O2—C2—C3125.55 (11)N1—C10—H10107.4
N1—C2—C3105.45 (10)C15—C10—H10107.4
O3—C3—N2128.81 (12)C11—C10—H10107.4
O3—C3—C2125.96 (11)C10—C11—C12109.47 (10)
N2—C3—C2105.22 (10)C10—C11—H11A109.8
N2—C4—C5111.47 (10)C12—C11—H11A109.8
N2—C4—C9109.93 (10)C10—C11—H11B109.8
C5—C4—C9111.89 (10)C12—C11—H11B109.8
N2—C4—H4107.8H11A—C11—H11B108.2
C5—C4—H4107.8C13—C12—C11110.82 (11)
C9—C4—H4107.8C13—C12—H12A109.5
C4—C5—C6109.97 (10)C11—C12—H12A109.5
C4—C5—H5A109.7C13—C12—H12B109.5
C6—C5—H5A109.7C11—C12—H12B109.5
C4—C5—H5B109.7H12A—C12—H12B108.1
C6—C5—H5B109.7C12—C13—C14110.77 (12)
H5A—C5—H5B108.2C12—C13—H13A109.5
C7—C6—C5111.69 (11)C14—C13—H13A109.5
C7—C6—H6A109.3C12—C13—H13B109.5
C5—C6—H6A109.3C14—C13—H13B109.5
C7—C6—H6B109.3H13A—C13—H13B108.1
C5—C6—H6B109.3C13—C14—C15111.56 (12)
H6A—C6—H6B107.9C13—C14—H14A109.3
C8—C7—C6110.79 (11)C15—C14—H14A109.3
C8—C7—H7A109.5C13—C14—H14B109.3
C6—C7—H7A109.5C15—C14—H14B109.3
C8—C7—H7B109.5H14A—C14—H14B108.0
C6—C7—H7B109.5C10—C15—C14109.49 (11)
H7A—C7—H7B108.1C10—C15—H15A109.8
C7—C8—C9111.59 (11)C14—C15—H15A109.8
C7—C8—H8A109.3C10—C15—H15B109.8
C9—C8—H8A109.3C14—C15—H15B109.8
C7—C8—H8B109.3H15A—C15—H15B108.2
C9—C8—H8B109.3C2—N1—C1110.60 (10)
H8A—C8—H8B108.0C2—N1—C10127.27 (10)
C4—C9—C8110.55 (11)C1—N1—C10121.98 (10)
C4—C9—H9A109.5C3—N2—C1110.76 (10)
C8—C9—H9A109.5C3—N2—C4126.14 (10)
C4—C9—H9B109.5C1—N2—C4122.96 (10)
C8—C9—H9B109.5
O2—C2—C3—O33.1 (2)O2—C2—N1—C101.1 (2)
N1—C2—C3—O3177.10 (12)C3—C2—N1—C10178.71 (11)
O2—C2—C3—N2177.10 (12)O1—C1—N1—C2177.91 (12)
N1—C2—C3—N22.67 (13)N2—C1—N1—C22.28 (14)
N2—C4—C5—C6179.59 (10)O1—C1—N1—C101.95 (19)
C9—C4—C5—C656.03 (14)N2—C1—N1—C10178.24 (10)
C4—C5—C6—C756.11 (15)C15—C10—N1—C276.87 (15)
C5—C6—C7—C856.18 (15)C11—C10—N1—C248.64 (16)
C6—C7—C8—C955.57 (15)C15—C10—N1—C198.38 (13)
N2—C4—C9—C8179.76 (10)C11—C10—N1—C1136.10 (12)
C5—C4—C9—C855.82 (14)O3—C3—N2—C1178.39 (13)
C7—C8—C9—C455.24 (15)C2—C3—N2—C11.36 (13)
N1—C10—C11—C12177.09 (10)O3—C3—N2—C45.9 (2)
C15—C10—C11—C1258.05 (14)C2—C3—N2—C4174.36 (11)
C10—C11—C12—C1357.32 (15)O1—C1—N2—C3179.78 (12)
C11—C12—C13—C1457.00 (16)N1—C1—N2—C30.41 (14)
C12—C13—C14—C1556.42 (17)O1—C1—N2—C43.89 (19)
N1—C10—C15—C14177.51 (12)N1—C1—N2—C4176.29 (10)
C11—C10—C15—C1457.06 (15)C5—C4—N2—C364.30 (16)
C13—C14—C15—C1055.77 (17)C9—C4—N2—C360.36 (15)
O2—C2—N1—C1176.75 (13)C5—C4—N2—C1120.46 (12)
C3—C2—N1—C13.01 (13)C9—C4—N2—C1114.87 (13)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1, N2, C1–C3 ring. <[C—H···(ring plane)] is ca. 43°.
D—H···AD—HH···AD···AD—H···A
C7—H7B···Cgi0.992.783.5511 (14)135
C11—H11B···O2ii0.992.513.2065 (18)127
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H22N2O3
Mr278.35
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)5.1980 (2), 21.7123 (10), 13.0244 (6)
β (°) 100.163 (2)
V3)1446.88 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.13 × 0.06 × 0.06
Data collection
DiffractometerBruker X8 Kappa CCD APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1998)
Tmin, Tmax0.989, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
38115, 3876, 2999
Rint0.049
(sin θ/λ)max1)0.685
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.104, 1.04
No. of reflections3876
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.18

Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1, N2, C1–C3 ring. <[C—H···(ring plane)] is ca. 43°.
D—H···AD—HH···AD···AD—H···A
C7—H7B···Cgi0.992.783.5511 (14)135
C11—H11B···O2ii0.992.513.2065 (18)127
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1, y, z.
 

Acknowledgements

The authors gratefully acknowledge the Fundação para a Ciência e a Tecnologia (FCT, MEC, Portugal), the European Union, QREN, FEDER, COMPETE for financial support by the strategic projects PEst-C/CTM/LA0011/2011 (to CICECO) and PEst-C/QUI/UI0062/2011 (to QOPNA), the R&D project PTDC/QUI-QUI/098098/2008 (FCOMP-01–0124-FEDER-010785), as well as the post-doctoral research grant SFRH/BPD/63736/2009 (to JAF). We further wish to thank the FCT for specific funding towards the purchase of the single-crystal X-ray diffractometer. We also thank the European Community's Seventh Framework Programme (FP7/2007–20139 under grant agreement No. 215009).

References

First citationBrandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2005). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFernandes, J. A., Almeida Paz, F. A., Marques, J., Marques, M. P. M. & Braga, S. S. (2011). Acta Cryst. C67, o57–o59.  Web of Science CSD CrossRef IUCr Journals
First citationLoughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075–o2076.  Web of Science CSD CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTalhi, O., Fernandes, J. A., Pinto, D. C. G. A., Silva, A. M. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o3243.  Web of Science CSD CrossRef IUCr Journals
First citationUlrichan, H. & Sayigh, D. A. A. R. (1965). J. Org. Chem. 30, 2781–2783.

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Volume 68| Part 11| November 2012| Pages o3233-o3234
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