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Acta Cryst. (2009). E65, o1188-o1189    [ doi:10.1107/S1600536809015918 ]

Ethyl 4-(2,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

H.-K. Fun, C. S. Yeap, M. Babu and B. Kalluraya

Abstract top

In the title compound, C14H14F2N2O3, the dihydropyrimidinone ring adopts a flattened boat conformation. The difluorophenyl group is disordered over two orientations with occupancies of 0.544 (3) and 0.456 (3). The methoxycarbonyl group is disordered over two positions with occupancies of 0.580 (8) and 0.420 (8). In the crystal, molecules are linked into centrosymmetric dimers by paired N-H...O hydrogen bonds and the dimers are linked into a ribbon-like structure along [100] by further N-H...O hydrogen bonds.

Comment top

Michael addition followed by aldol condensation known as the Robinson's annulation is synthetically a very useful reaction for the construction of six-membered cyclic compounds (Kalluraya and Rai, 2003). 3,4-Dihydro-pyrimidinones are compounds that have drawn wide-spread attention, due to their pharmaceutical applications (Atwal, 1990; Sadanandam et al., 1992). The common synthetic routes to these compounds generally involve multi-step transformation, which are essentially based on the Biginelli condensation methodology (Steele et al., 1998). These pyrimidinones are also associated with activities like calcium channel blocking (Manjula et al., 2004). We synthesized the title compound by means of Robinson's annulation employing the microwave technique, and its crystal structure is reported here.

Bond lengths (Allen et al., 1987) and angles in the title molecule (Fig. 1) are within normal ranges. The dihydropyrimidinone ring adopts a flattened boat conformation, with puckering parameters Q = 0.170 (2) Å, Θ = 97.4 (7)° and φ = 254.4 (7)°.

The difluorophenyl group is disordered over two positions with occupancies of 0.544 (3) and 0.456 (3). The caboxylate methyl group is also disordered over two positions with occupancies of 0.580 (8) and 0.420 (8).

In the crystal structure, the molecules are linked into centrosymmetric dimers by means of paired N—H···O hydrogen bonds (Table 1). The dimers are linked into a chain along the [100] again by N—H···O hydrogen bonds (Fig. 2).

Related literature top

For general background and pharmaceutical applications of pyrimidinones, see: Kalluraya & Rai (2003); Atwal (1990); Sadanandam et al. (1992); Steele et al. (1998); Manjula et al. (2004). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2,4-difluoro benzaldehyde (0.01 mol), ethyl acetoacetate (0.015 mol), thiourea (0.01 mol) and conc. H2SO4 (2 drops) in absolute alcohol (10 ml) taken in a beaker (100 ml) was zapped inside a microwave oven for 3 min at 160 Watt (i.e. 25% MW power). The reaction mixture was then allowed to stand at room temperature and the product formed was filtered, washed with ethanol followed by water and dried. Further purification was done by recrystallisation from ethanol. Single crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Refinement top

Atoms H1N1 and H1N2 were located in a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93–0.98 Å and Uiso(H) = 1.2-1.5 Ueq(C). A rotating-group model was applied for the methyl group. The difluorophenyl group is disordered over two positions with occupancies of 0.544 (3) and 0.456 (3). The caboxylate methyl group is also disordered over two positions with occupancies of 0.580 (8) and 0.420 (8). For the disordered difluorophenyl group, the same Uij parameters were used for atom pairs F1A/F1B, C1A/C1B, and C5A/C5B, and all disordered atoms were subjected to a rigid bond restraint.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. All disorder components are shown.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the b axis, showing chains along the [100]. Hydrogen bonds are shown as dashed lines. Only major disorder components are shown.
Ethyl 4-(2,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate top
Crystal data top
C14H14F2N2O3Z = 2
Mr = 296.27F000 = 308
Triclinic, P1Dx = 1.466 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.5176 (1) ÅCell parameters from 7927 reflections
b = 8.0483 (1) Åθ = 2.7–34.4º
c = 11.9323 (2) ŵ = 0.12 mm−1
α = 90.147 (1)ºT = 100 K
β = 100.839 (1)ºPlate, colourless
γ = 108.421 (1)º0.43 × 0.32 × 0.13 mm
V = 671.248 (17) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3075 independent reflections
Radiation source: fine-focus sealed tube2703 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 100 Kθmax = 27.5º
φ and ω scansθmin = 2.7º
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −9→9
Tmin = 0.949, Tmax = 0.985k = −10→10
17515 measured reflectionsl = −15→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.173  w = 1/[σ2(Fo2) + (0.0607P)2 + 0.8775P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3075 reflectionsΔρmax = 0.66 e Å−3
266 parametersΔρmin = −0.84 e Å−3
45 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C14H14F2N2O3γ = 108.421 (1)º
Mr = 296.27V = 671.248 (17) Å3
Triclinic, P1Z = 2
a = 7.5176 (1) ÅMo Kα
b = 8.0483 (1) ŵ = 0.12 mm−1
c = 11.9323 (2) ÅT = 100 K
α = 90.147 (1)º0.43 × 0.32 × 0.13 mm
β = 100.839 (1)º
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3075 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2703 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.985Rint = 0.028
17515 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06845 restraints
wR(F2) = 0.173H atoms treated by a mixture of
independent and constrained refinement
S = 1.08Δρmax = 0.66 e Å−3
3075 reflectionsΔρmin = −0.84 e Å−3
266 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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*/UeqOcc. (<1)
F1A0.7550 (6)0.3028 (5)0.3410 (3)0.0598 (8)0.544 (3)
F1B0.8268 (7)0.8571 (6)0.2813 (4)0.0598 (8)0.456 (3)
O10.3876 (2)0.1588 (2)0.01956 (16)0.0352 (4)
O21.2723 (2)0.5461 (2)0.14780 (15)0.0298 (4)
O31.1456 (2)0.7375 (2)0.20789 (18)0.0428 (5)
N10.5906 (2)0.4172 (2)0.10712 (14)0.0207 (4)
N20.7014 (2)0.1862 (2)0.07956 (16)0.0234 (4)
F2A0.7967 (7)0.7696 (9)0.6102 (3)0.0959 (19)0.544 (3)
C1A0.7750 (7)0.4770 (8)0.3704 (4)0.0279 (8)0.544 (3)
C2A0.7792 (9)0.5355 (13)0.4811 (5)0.0557 (19)0.544 (3)
H2AA0.77190.45860.53940.067*0.544 (3)
C3A0.7941 (12)0.7054 (15)0.5035 (6)0.061 (2)0.544 (3)
C4A0.8048 (8)0.8278 (10)0.4216 (5)0.0520 (16)0.544 (3)
H4AA0.81310.94330.43810.062*0.544 (3)
C5A0.8022 (7)0.7640 (8)0.3129 (5)0.0332 (10)0.544 (3)
H5AA0.81070.84230.25540.040*0.544 (3)
C6A0.788 (3)0.5949 (12)0.2835 (7)0.0180 (17)0.544 (3)
F2B0.7660 (6)0.6163 (6)0.6323 (2)0.0479 (11)0.456 (3)
C1B0.8051 (8)0.7153 (9)0.3476 (5)0.0279 (8)0.456 (3)
C2B0.8046 (11)0.7414 (8)0.4604 (6)0.0255 (14)0.456 (3)
H2BA0.82650.85190.49450.031*0.456 (3)
C3B0.7694 (10)0.5921 (9)0.5204 (5)0.0275 (13)0.456 (3)
C4B0.7384 (11)0.4271 (8)0.4734 (5)0.0345 (14)0.456 (3)
H4BA0.71250.33260.51930.041*0.456 (3)
C5B0.7443 (9)0.3954 (11)0.3573 (5)0.0332 (10)0.456 (3)
H5BA0.73010.28530.32560.040*0.456 (3)
C6B0.774 (3)0.5502 (15)0.2934 (11)0.025 (3)0.456 (3)
C70.7793 (3)0.5371 (3)0.16198 (16)0.0182 (4)
H7A0.79950.64330.11950.022*0.580 (8)
H7B0.79850.63850.11780.022*0.420 (8)
C80.5505 (3)0.2516 (3)0.06653 (18)0.0234 (4)
C90.8906 (3)0.2904 (3)0.11002 (16)0.0197 (4)
C100.9344 (3)0.4608 (3)0.14452 (15)0.0179 (4)
C111.1330 (3)0.5786 (3)0.16561 (16)0.0198 (4)
C121.3361 (4)0.8646 (4)0.2385 (3)0.0541 (9)
H12A1.37170.92510.17180.065*0.580 (8)
H12B1.42830.80570.26700.065*0.580 (8)
H12C1.42230.82590.20190.065*0.420 (8)
H12D1.33320.97630.20930.065*0.420 (8)
C13A1.3350 (6)0.9926 (6)0.3285 (4)0.0367 (13)0.580 (8)
H13A1.46291.07000.35590.055*0.580 (8)
H13B1.28660.93050.39080.055*0.580 (8)
H13C1.25461.05990.29700.055*0.580 (8)
C13B1.4024 (9)0.8870 (8)0.3480 (5)0.0355 (17)0.420 (8)
H13D1.43070.78410.37500.053*0.420 (8)
H13E1.30850.90700.38610.053*0.420 (8)
H13F1.51700.98660.36400.053*0.420 (8)
C141.0280 (3)0.1943 (3)0.09888 (19)0.0242 (4)
H14A1.13890.23650.15910.036*
H14B1.06570.21380.02620.036*
H14C0.96760.07100.10420.036*
H1N10.493 (4)0.458 (4)0.105 (2)0.034 (7)*
H1N20.674 (4)0.081 (4)0.052 (2)0.035 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.078 (2)0.0668 (19)0.0584 (16)0.0393 (16)0.0423 (15)0.0248 (14)
F1B0.078 (2)0.0668 (19)0.0584 (16)0.0393 (16)0.0423 (15)0.0248 (14)
O10.0139 (7)0.0315 (8)0.0586 (11)0.0057 (6)0.0059 (7)−0.0174 (8)
O20.0166 (7)0.0307 (8)0.0447 (9)0.0085 (6)0.0107 (6)0.0018 (7)
O30.0160 (8)0.0346 (9)0.0721 (13)−0.0006 (7)0.0104 (8)−0.0262 (9)
N10.0141 (8)0.0243 (9)0.0253 (8)0.0088 (7)0.0032 (6)−0.0036 (7)
N20.0160 (8)0.0206 (8)0.0350 (10)0.0063 (7)0.0081 (7)−0.0045 (7)
F2A0.081 (3)0.165 (5)0.0359 (19)0.034 (3)0.0086 (18)−0.043 (3)
C1A0.0253 (17)0.047 (2)0.0141 (15)0.0144 (16)0.0068 (12)0.0079 (16)
C2A0.039 (3)0.102 (6)0.023 (3)0.018 (4)0.008 (2)0.002 (4)
C3A0.039 (3)0.112 (7)0.026 (4)0.018 (5)0.003 (3)−0.023 (4)
C4A0.030 (3)0.071 (4)0.049 (3)0.012 (3)0.002 (2)−0.039 (3)
C5A0.0261 (18)0.051 (3)0.0162 (16)0.0024 (17)0.0063 (13)−0.0106 (19)
C6A0.010 (3)0.031 (5)0.012 (2)0.004 (4)0.0039 (16)−0.003 (2)
F2B0.079 (3)0.073 (3)0.0113 (13)0.051 (2)0.0125 (14)0.0029 (15)
C1B0.0253 (17)0.047 (2)0.0141 (15)0.0144 (16)0.0068 (12)0.0079 (16)
C2B0.040 (3)0.017 (2)0.025 (3)0.019 (2)0.002 (3)−0.002 (2)
C3B0.041 (3)0.036 (3)0.015 (3)0.023 (3)0.008 (2)0.005 (2)
C4B0.058 (4)0.028 (3)0.028 (3)0.023 (3)0.016 (3)0.011 (2)
C5B0.0261 (18)0.051 (3)0.0162 (16)0.0024 (17)0.0063 (13)−0.0106 (19)
C6B0.016 (4)0.025 (5)0.036 (5)0.008 (5)0.005 (3)−0.005 (3)
C70.0150 (9)0.0218 (9)0.0189 (9)0.0073 (7)0.0039 (7)−0.0009 (7)
C80.0159 (9)0.0252 (10)0.0304 (10)0.0067 (8)0.0080 (8)−0.0038 (8)
C90.0156 (9)0.0262 (10)0.0196 (9)0.0084 (8)0.0062 (7)0.0020 (7)
C100.0144 (9)0.0250 (10)0.0159 (8)0.0081 (7)0.0043 (7)0.0012 (7)
C110.0173 (9)0.0269 (10)0.0162 (8)0.0082 (8)0.0041 (7)0.0013 (7)
C120.0205 (12)0.0508 (17)0.078 (2)−0.0088 (11)0.0148 (13)−0.0355 (15)
C13A0.033 (2)0.028 (2)0.042 (2)0.0054 (17)−0.0014 (18)−0.0057 (17)
C13B0.032 (3)0.035 (3)0.034 (3)0.007 (2)−0.001 (2)−0.006 (2)
C140.0198 (10)0.0261 (10)0.0308 (11)0.0112 (8)0.0085 (8)0.0002 (8)
Geometric parameters (Å, °) top
F1A—C1A1.398 (6)C3B—C4B1.373 (8)
F1B—C1B1.375 (7)C4B—C5B1.418 (8)
O1—C81.238 (3)C4B—H4BA0.93
O2—C111.211 (2)C5B—C6B1.441 (12)
O3—C111.342 (3)C5B—H5BA0.93
O3—C121.451 (3)C6B—C71.579 (12)
N1—C81.337 (3)C7—C101.524 (3)
N1—C71.468 (2)C7—H7A0.98
N1—H1N10.89 (3)C7—H7B0.96
N2—C81.379 (3)C9—C101.349 (3)
N2—C91.382 (3)C9—C141.496 (3)
N2—H1N20.86 (3)C10—C111.467 (3)
F2A—C3A1.367 (7)C12—C13B1.299 (7)
C1A—C2A1.392 (8)C12—C13A1.490 (5)
C1A—C6A1.404 (9)C12—H12A0.97
C2A—C3A1.358 (11)C12—H12B0.97
C2A—H2AA0.93C12—H12C0.97
C3A—C4A1.384 (11)C12—H12D0.97
C4A—C5A1.388 (7)C13A—H12D1.4259
C4A—H4AA0.93C13A—H13A0.96
C5A—C6A1.371 (11)C13A—H13B0.96
C5A—H5AA0.93C13A—H13C0.96
C6A—C71.505 (8)C13B—H13D0.96
F2B—C3B1.355 (6)C13B—H13E0.96
C1B—C2B1.362 (8)C13B—H13F0.96
C1B—C6B1.409 (12)C14—H14A0.96
C2B—C3B1.378 (7)C14—H14B0.96
C2B—H2BA0.93C14—H14C0.96
C11—O3—C12116.68 (18)C10—C7—H7B104.8
C8—N1—C7126.65 (17)C6B—C7—H7B121.4
C8—N1—H1N1117.3 (18)O1—C8—N1123.06 (19)
C7—N1—H1N1115.9 (18)O1—C8—N2120.41 (19)
C8—N2—C9123.28 (18)N1—C8—N2116.53 (18)
C8—N2—H1N2115 (2)C10—C9—N2119.93 (18)
C9—N2—H1N2120 (2)C10—C9—C14126.95 (18)
C2A—C1A—F1A122.6 (6)N2—C9—C14113.12 (17)
C2A—C1A—C6A119.6 (7)C9—C10—C11120.89 (17)
F1A—C1A—C6A117.9 (5)C9—C10—C7121.08 (17)
C3A—C2A—C1A119.6 (6)C11—C10—C7118.04 (17)
C3A—C2A—H2AA120.2O2—C11—O3121.61 (18)
C1A—C2A—H2AA120.2O2—C11—C10127.53 (19)
C2A—C3A—F2A122.2 (8)O3—C11—C10110.85 (16)
C2A—C3A—C4A123.8 (6)C13B—C12—O3113.2 (4)
F2A—C3A—C4A114.0 (8)C13B—C12—C13A46.9 (3)
C3A—C4A—C5A114.5 (6)O3—C12—C13A108.3 (3)
C3A—C4A—H4AA122.7C13B—C12—H12A135.7
C5A—C4A—H4AA122.7O3—C12—H12A110.0
C6A—C5A—C4A125.2 (7)C13A—C12—H12A110.0
C6A—C5A—H5AA117.4C13B—C12—H12B64.7
C4A—C5A—H5AA117.4O3—C12—H12B110.0
C5A—C6A—C1A117.2 (6)C13A—C12—H12B110.0
C5A—C6A—C7121.1 (7)H12A—C12—H12B108.4
C1A—C6A—C7121.6 (7)C13B—C12—H12C108.9
C2B—C1B—F1B118.1 (6)O3—C12—H12C108.9
C2B—C1B—C6B124.0 (7)C13A—C12—H12C141.9
F1B—C1B—C6B117.9 (6)H12A—C12—H12C63.9
C1B—C2B—C3B115.2 (5)H12B—C12—H12C48.0
C1B—C2B—H2BA122.4C13B—C12—H12D109.0
C3B—C2B—H2BA122.4O3—C12—H12D109.0
F2B—C3B—C4B120.2 (5)C13A—C12—H12D67.0
F2B—C3B—C2B115.7 (6)H12A—C12—H12D46.1
C4B—C3B—C2B124.1 (5)H12B—C12—H12D139.4
C3B—C4B—C5B122.4 (6)H12C—C12—H12D107.8
C3B—C4B—H4BA118.8C12—C13A—H13A109.5
C5B—C4B—H4BA118.8H12D—C13A—H13A100.8
C4B—C5B—C6B113.6 (8)C12—C13A—H13B109.5
C4B—C5B—H5BA123.2H12D—C13A—H13B143.5
C6B—C5B—H5BA123.2C12—C13A—H13C109.5
C1B—C6B—C5B120.6 (9)H12D—C13A—H13C77.8
C1B—C6B—C7119.2 (7)C12—C13B—H13D109.5
C5B—C6B—C7120.1 (8)C12—C13B—H13E109.5
N1—C7—C6A113.1 (6)H13D—C13B—H13E109.5
N1—C7—C10109.82 (15)C12—C13B—H13F109.5
C6A—C7—C10115.3 (7)H13D—C13B—H13F109.5
N1—C7—C6B105.6 (8)H13E—C13B—H13F109.5
C10—C7—C6B110.0 (8)C9—C14—H14A109.5
N1—C7—H7A105.9C9—C14—H14B109.5
C6A—C7—H7A105.9H14A—C14—H14B109.5
C10—C7—H7A105.9C9—C14—H14C109.5
C6B—C7—H7A119.3H14A—C14—H14C109.5
N1—C7—H7B104.8H14B—C14—H14C109.5
C6A—C7—H7B108.1
F1A—C1A—C2A—C3A−178.4 (6)C5A—C6A—C7—C6B−168 (8)
C6A—C1A—C2A—C3A0.7 (12)C1A—C6A—C7—C6B10 (5)
C1A—C2A—C3A—F2A179.2 (6)C1B—C6B—C7—N1−120.8 (15)
C1A—C2A—C3A—C4A0.3 (12)C5B—C6B—C7—N160.9 (18)
C2A—C3A—C4A—C5A−1.0 (11)C1B—C6B—C7—C6A5(5)
F2A—C3A—C4A—C5A−180.0 (5)C5B—C6B—C7—C6A−173 (8)
C3A—C4A—C5A—C6A0.8 (12)C1B—C6B—C7—C10120.7 (15)
C4A—C5A—C6A—C1A0.1 (18)C5B—C6B—C7—C10−57.6 (18)
C4A—C5A—C6A—C7177.7 (8)C7—N1—C8—O1−178.9 (2)
C2A—C1A—C6A—C5A−0.9 (17)C7—N1—C8—N21.3 (3)
F1A—C1A—C6A—C5A178.2 (9)C9—N2—C8—O1166.8 (2)
C2A—C1A—C6A—C7−178.4 (9)C9—N2—C8—N1−13.3 (3)
F1A—C1A—C6A—C70.6 (17)C8—N2—C9—C109.5 (3)
F1B—C1B—C2B—C3B175.8 (6)C8—N2—C9—C14−169.96 (19)
C6B—C1B—C2B—C3B−0.7 (16)N2—C9—C10—C11−173.48 (17)
C1B—C2B—C3B—F2B−179.1 (5)C14—C9—C10—C116.0 (3)
C1B—C2B—C3B—C4B0.7 (12)N2—C9—C10—C76.1 (3)
F2B—C3B—C4B—C5B−178.7 (6)C14—C9—C10—C7−174.45 (18)
C2B—C3B—C4B—C5B1.5 (12)N1—C7—C10—C9−15.5 (2)
C3B—C4B—C5B—C6B−3.4 (14)C6A—C7—C10—C9113.7 (5)
C2B—C1B—C6B—C5B−1(3)C6B—C7—C10—C9100.3 (6)
F1B—C1B—C6B—C5B−178.0 (13)N1—C7—C10—C11164.14 (16)
C2B—C1B—C6B—C7−179.8 (10)C6A—C7—C10—C11−66.7 (5)
F1B—C1B—C6B—C74(2)C6B—C7—C10—C11−80.1 (6)
C4B—C5B—C6B—C1B3(2)C12—O3—C11—O2−4.1 (3)
C4B—C5B—C6B—C7−178.4 (12)C12—O3—C11—C10176.8 (2)
C8—N1—C7—C6A−118.4 (5)C9—C10—C11—O26.0 (3)
C8—N1—C7—C1012.0 (3)C7—C10—C11—O2−173.63 (19)
C8—N1—C7—C6B−106.5 (7)C9—C10—C11—O3−174.99 (18)
C5A—C6A—C7—N1−109.7 (12)C7—C10—C11—O35.4 (2)
C1A—C6A—C7—N167.8 (15)C11—O3—C12—C13B−104.0 (4)
C5A—C6A—C7—C10122.8 (12)C11—O3—C12—C13A−154.2 (3)
C1A—C6A—C7—C10−59.7 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.89 (3)2.14 (3)3.007 (2)165 (2)
N2—H1N2···O1ii0.86 (3)1.99 (3)2.840 (2)177 (3)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.89 (3)2.14 (3)3.007 (2)165 (2)
N2—H1N2···O1ii0.86 (3)1.99 (3)2.840 (2)177 (3)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z.
Acknowledgements top

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of a post of research officer under the Science Fund (grant No. 305/PFIZIK/613312).

references
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