organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

6-(3,5-Di­methyl­benz­yl)-5-ethyl-1-[(3-phenyl­prop­­oxy)meth­yl]-1,2,3,4-tetra­hydro­pyrimidine-2,4-dione

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 19 December 2011; accepted 26 December 2011; online 11 January 2012)

The pyrimidine ring of the title compound, C25H30N2O3, is approximately planar (r.m.s. deviation = 0.003 Å); the C atom at the 5-position deviates by 0.012 (3) Å from the mean plane and the C atom at the 6-position by 0.038 (3) Å. In the mol­ecule, the pyrimidine ring is oriented at 86.72 (9) and 59.75 (9)° with respect to the two benzene rings, and the two benzene rings are inclined to each other at 58.35 (9)°. In the crystal, the amino group is hydrogen-bond donor to the exocyclic O atom at the 4-position of an adjacent mol­ecule, the hydrogen bond generating an inversion dimer.

Related literature

For the applications and synthesis of the title compound, see: El-Brollosy et al. (2009[El-Brollosy, N. R., Al-Deeb, O. A., El-Emam, A. A., Pedersen, E. B., La Colla, P., Collu, G., Sanna, G. & Loddo, R. (2009). Arch. Pharm. Chem. Life Sci. 342, 663-670.]).

[Scheme 1]

Experimental

Crystal data
  • C25H30N2O3

  • Mr = 406.51

  • Triclinic, [P \overline 1]

  • a = 4.8276 (4) Å

  • b = 14.9398 (10) Å

  • c = 15.4574 (12) Å

  • α = 76.949 (6)°

  • β = 89.296 (6)°

  • γ = 88.267 (6)°

  • V = 1085.53 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.980, Tmax = 0.996

  • 7623 measured reflections

  • 4974 independent reflections

  • 3719 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.167

  • S = 1.04

  • 4974 reflections

  • 277 parameters

  • 1 restraint

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

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.89 (1) 1.94 (1) 2.826 (2) 178 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The compound (Scheme I) was synthesized for an evaluation of its anti-viral activity against HIV-1 (El-Brollosy et al., 2009). The pyrimidine ring is planar; the C atom at the 5-position deviates by 0.012 (3) Å from the mean plane and the C atom at the 6-position by 0.038 (3) Å (Fig. 1). The amino group is hydrogen-bond donor to the exocyclic O atom at the 4-position, the hydrogen bond generating a centrosymmetric dimer (Table 1, Fig. 1).

Related literature top

For the applications and synthesis of the title compound, see: El-Brollosy et al. (2009).

Experimental top

The compound was synthesized by using a reported method (El-Brollosy et al., 2009), and was recrystallized from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.99 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; its temperature factor was refined.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C25H30N2O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Dimeric hydrogen-bonded structure.
6-(3,5-Dimethylbenzyyl)-5-ethyl-1-[(3-phenylpropoxy)methyl]-1,2,3,4- tetrahydropyrimidine-2,4-dione top
Crystal data top
C25H30N2O3Z = 2
Mr = 406.51F(000) = 436
Triclinic, P1Dx = 1.244 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8276 (4) ÅCell parameters from 2909 reflections
b = 14.9398 (10) Åθ = 2.7–27.5°
c = 15.4574 (12) ŵ = 0.08 mm1
α = 76.949 (6)°T = 100 K
β = 89.296 (6)°Prism, colorless
γ = 88.267 (6)°0.25 × 0.20 × 0.05 mm
V = 1085.53 (14) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
4974 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3719 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.039
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 2.7°
ω scanh = 64
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 1919
Tmin = 0.980, Tmax = 0.996l = 2018
7623 measured reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0802P)2 + 0.2053P]
where P = (Fo2 + 2Fc2)/3
4974 reflections(Δ/σ)max = 0.001
277 parametersΔρmax = 0.39 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C25H30N2O3γ = 88.267 (6)°
Mr = 406.51V = 1085.53 (14) Å3
Triclinic, P1Z = 2
a = 4.8276 (4) ÅMo Kα radiation
b = 14.9398 (10) ŵ = 0.08 mm1
c = 15.4574 (12) ÅT = 100 K
α = 76.949 (6)°0.25 × 0.20 × 0.05 mm
β = 89.296 (6)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
4974 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
3719 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.996Rint = 0.039
7623 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.39 e Å3
4974 reflectionsΔρmin = 0.29 e Å3
277 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7285 (3)0.74030 (9)0.40923 (8)0.0227 (3)
O20.2592 (3)0.47945 (8)0.42401 (8)0.0216 (3)
O30.2541 (3)0.89685 (8)0.27377 (8)0.0188 (3)
N10.4879 (3)0.61150 (10)0.41488 (9)0.0167 (3)
H10.572 (4)0.5837 (12)0.4647 (8)0.014 (5)*
N20.4166 (3)0.73931 (10)0.29812 (9)0.0151 (3)
C10.5563 (4)0.69986 (12)0.37641 (11)0.0169 (4)
C20.2987 (4)0.55921 (12)0.38339 (11)0.0174 (4)
C30.1581 (4)0.60349 (12)0.30160 (11)0.0160 (4)
C40.2187 (4)0.69150 (12)0.26177 (11)0.0156 (4)
C50.0516 (4)0.54575 (12)0.26870 (12)0.0186 (4)
H5A0.19990.58690.23670.022*
H5B0.13760.50440.32050.022*
C60.0717 (4)0.48772 (14)0.20714 (13)0.0276 (5)
H6A0.07490.45260.18810.041*
H6B0.21470.44530.23890.041*
H6C0.15420.52810.15500.041*
C70.0796 (4)0.74447 (12)0.17790 (11)0.0174 (4)
H7A0.00810.80380.18870.021*
H7B0.08220.70960.16670.021*
C80.2569 (4)0.76452 (12)0.09395 (11)0.0165 (4)
C90.4438 (4)0.69892 (12)0.07253 (12)0.0184 (4)
H90.46700.64070.11240.022*
C100.5962 (4)0.71790 (13)0.00650 (12)0.0208 (4)
C110.5603 (4)0.80409 (13)0.06396 (12)0.0217 (4)
H110.66500.81780.11750.026*
C120.3753 (4)0.87043 (13)0.04483 (12)0.0230 (4)
C130.2259 (4)0.84895 (12)0.03477 (12)0.0195 (4)
H130.09910.89360.04880.023*
C140.7919 (4)0.64610 (15)0.03046 (13)0.0297 (5)
H14A0.95920.67570.05840.045*
H14B0.70050.61580.07190.045*
H14C0.84290.60030.02340.045*
C150.3370 (5)0.96336 (14)0.10683 (13)0.0317 (5)
H15A0.36281.01150.07410.048*
H15B0.14970.96930.13160.048*
H15C0.47350.96970.15510.048*
C160.4702 (4)0.83684 (11)0.25921 (11)0.0169 (4)
H16A0.64280.85360.28490.020*
H16B0.50000.84490.19450.020*
C170.2175 (4)0.90085 (12)0.36571 (11)0.0197 (4)
H17A0.39960.90410.39340.024*
H17B0.12420.84520.39890.024*
C180.0417 (4)0.98597 (12)0.36809 (12)0.0202 (4)
H18A0.01940.98320.43000.024*
H18B0.12600.98630.33180.024*
C190.1936 (4)1.07554 (12)0.33360 (13)0.0230 (4)
H19A0.36191.07520.36970.028*
H19B0.25361.07870.27150.028*
C200.0166 (4)1.15986 (12)0.33684 (12)0.0192 (4)
C210.1760 (4)1.19492 (13)0.27088 (12)0.0226 (4)
H210.18781.16790.22100.027*
C220.3515 (4)1.26880 (13)0.27654 (13)0.0248 (4)
H220.48381.29120.23120.030*
C230.3344 (4)1.31006 (13)0.34816 (13)0.0240 (4)
H230.45671.35980.35280.029*
C240.1361 (4)1.27772 (13)0.41292 (12)0.0232 (4)
H240.11871.30670.46120.028*
C250.0366 (4)1.20321 (12)0.40744 (12)0.0207 (4)
H250.17031.18140.45240.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0282 (7)0.0184 (7)0.0228 (7)0.0030 (6)0.0061 (6)0.0063 (5)
O20.0311 (7)0.0122 (6)0.0209 (6)0.0008 (5)0.0045 (6)0.0022 (5)
O30.0256 (7)0.0144 (6)0.0171 (6)0.0028 (5)0.0006 (5)0.0060 (5)
N10.0237 (8)0.0121 (7)0.0137 (7)0.0013 (6)0.0042 (6)0.0020 (6)
N20.0192 (7)0.0118 (7)0.0145 (7)0.0008 (6)0.0002 (6)0.0036 (6)
C10.0189 (9)0.0156 (9)0.0175 (8)0.0010 (7)0.0010 (7)0.0067 (7)
C20.0201 (9)0.0144 (8)0.0190 (9)0.0007 (7)0.0032 (7)0.0067 (7)
C30.0174 (9)0.0157 (9)0.0160 (8)0.0021 (7)0.0010 (7)0.0065 (7)
C40.0183 (8)0.0146 (9)0.0147 (8)0.0020 (7)0.0019 (7)0.0057 (7)
C50.0208 (9)0.0144 (9)0.0205 (9)0.0008 (7)0.0019 (7)0.0039 (7)
C60.0350 (11)0.0242 (10)0.0277 (10)0.0064 (9)0.0021 (9)0.0138 (8)
C70.0188 (9)0.0152 (9)0.0177 (8)0.0009 (7)0.0003 (7)0.0031 (7)
C80.0196 (9)0.0159 (9)0.0150 (8)0.0018 (7)0.0023 (7)0.0053 (7)
C90.0216 (9)0.0168 (9)0.0175 (8)0.0004 (7)0.0040 (7)0.0053 (7)
C100.0206 (9)0.0242 (10)0.0195 (9)0.0012 (8)0.0029 (7)0.0088 (8)
C110.0242 (10)0.0257 (10)0.0168 (9)0.0047 (8)0.0026 (7)0.0076 (8)
C120.0336 (11)0.0190 (9)0.0170 (9)0.0042 (8)0.0011 (8)0.0047 (7)
C130.0263 (10)0.0155 (9)0.0177 (8)0.0017 (7)0.0023 (7)0.0062 (7)
C140.0300 (11)0.0360 (12)0.0249 (10)0.0083 (9)0.0005 (8)0.0117 (9)
C150.0512 (14)0.0206 (10)0.0223 (10)0.0020 (9)0.0085 (9)0.0033 (8)
C160.0214 (9)0.0117 (8)0.0174 (8)0.0006 (7)0.0025 (7)0.0032 (7)
C170.0275 (10)0.0169 (9)0.0162 (8)0.0011 (8)0.0036 (7)0.0067 (7)
C180.0242 (9)0.0174 (9)0.0212 (9)0.0025 (7)0.0046 (7)0.0087 (7)
C190.0246 (10)0.0162 (9)0.0304 (10)0.0007 (8)0.0049 (8)0.0097 (8)
C200.0205 (9)0.0143 (9)0.0237 (9)0.0055 (7)0.0068 (7)0.0058 (7)
C210.0276 (10)0.0193 (9)0.0233 (9)0.0048 (8)0.0020 (8)0.0092 (8)
C220.0259 (10)0.0195 (10)0.0282 (10)0.0029 (8)0.0055 (8)0.0032 (8)
C230.0249 (10)0.0150 (9)0.0320 (10)0.0001 (8)0.0035 (8)0.0055 (8)
C240.0303 (10)0.0195 (9)0.0219 (9)0.0023 (8)0.0043 (8)0.0094 (8)
C250.0231 (9)0.0175 (9)0.0215 (9)0.0027 (7)0.0002 (7)0.0041 (7)
Geometric parameters (Å, º) top
O1—C11.222 (2)C12—C131.397 (3)
O2—C21.234 (2)C12—C151.506 (3)
O3—C161.404 (2)C13—H130.9500
O3—C171.444 (2)C14—H14A0.9800
N1—C11.368 (2)C14—H14B0.9800
N1—C21.381 (2)C14—H14C0.9800
N1—H10.885 (9)C15—H15A0.9800
N2—C11.393 (2)C15—H15B0.9800
N2—C41.405 (2)C15—H15C0.9800
N2—C161.475 (2)C16—H16A0.9900
C2—C31.454 (2)C16—H16B0.9900
C3—C41.359 (2)C17—C181.514 (2)
C3—C51.514 (2)C17—H17A0.9900
C4—C71.511 (2)C17—H17B0.9900
C5—C61.529 (3)C18—C191.530 (3)
C5—H5A0.9900C18—H18A0.9900
C5—H5B0.9900C18—H18B0.9900
C6—H6A0.9800C19—C201.511 (2)
C6—H6B0.9800C19—H19A0.9900
C6—H6C0.9800C19—H19B0.9900
C7—C81.523 (2)C20—C211.390 (3)
C7—H7A0.9900C20—C251.395 (3)
C7—H7B0.9900C21—C221.389 (3)
C8—C131.386 (2)C21—H210.9500
C8—C91.404 (2)C22—C231.388 (3)
C9—C101.395 (2)C22—H220.9500
C9—H90.9500C23—C241.389 (3)
C10—C111.397 (3)C23—H230.9500
C10—C141.513 (3)C24—C251.388 (3)
C11—C121.393 (3)C24—H240.9500
C11—H110.9500C25—H250.9500
C16—O3—C17113.95 (13)C10—C14—H14A109.5
C1—N1—C2126.47 (14)C10—C14—H14B109.5
C1—N1—H1118.3 (13)H14A—C14—H14B109.5
C2—N1—H1115.2 (13)C10—C14—H14C109.5
C1—N2—C4122.09 (14)H14A—C14—H14C109.5
C1—N2—C16116.28 (14)H14B—C14—H14C109.5
C4—N2—C16121.44 (14)C12—C15—H15A109.5
O1—C1—N1121.59 (16)C12—C15—H15B109.5
O1—C1—N2123.13 (16)H15A—C15—H15B109.5
N1—C1—N2115.28 (15)C12—C15—H15C109.5
O2—C2—N1119.97 (15)H15A—C15—H15C109.5
O2—C2—C3123.88 (16)H15B—C15—H15C109.5
N1—C2—C3116.15 (15)O3—C16—N2113.40 (14)
C4—C3—C2119.14 (16)O3—C16—H16A108.9
C4—C3—C5125.36 (15)N2—C16—H16A108.9
C2—C3—C5115.50 (15)O3—C16—H16B108.9
C3—C4—N2120.86 (15)N2—C16—H16B108.9
C3—C4—C7123.32 (16)H16A—C16—H16B107.7
N2—C4—C7115.82 (14)O3—C17—C18107.67 (14)
C3—C5—C6113.79 (15)O3—C17—H17A110.2
C3—C5—H5A108.8C18—C17—H17A110.2
C6—C5—H5A108.8O3—C17—H17B110.2
C3—C5—H5B108.8C18—C17—H17B110.2
C6—C5—H5B108.8H17A—C17—H17B108.5
H5A—C5—H5B107.7C17—C18—C19113.32 (15)
C5—C6—H6A109.5C17—C18—H18A108.9
C5—C6—H6B109.5C19—C18—H18A108.9
H6A—C6—H6B109.5C17—C18—H18B108.9
C5—C6—H6C109.5C19—C18—H18B108.9
H6A—C6—H6C109.5H18A—C18—H18B107.7
H6B—C6—H6C109.5C20—C19—C18112.78 (15)
C4—C7—C8116.78 (14)C20—C19—H19A109.0
C4—C7—H7A108.1C18—C19—H19A109.0
C8—C7—H7A108.1C20—C19—H19B109.0
C4—C7—H7B108.1C18—C19—H19B109.0
C8—C7—H7B108.1H19A—C19—H19B107.8
H7A—C7—H7B107.3C21—C20—C25118.12 (17)
C13—C8—C9118.59 (16)C21—C20—C19120.98 (16)
C13—C8—C7119.19 (16)C25—C20—C19120.87 (17)
C9—C8—C7122.17 (15)C22—C21—C20121.14 (17)
C10—C9—C8120.99 (17)C22—C21—H21119.4
C10—C9—H9119.5C20—C21—H21119.4
C8—C9—H9119.5C23—C22—C21120.25 (18)
C11—C10—C9118.59 (17)C23—C22—H22119.9
C11—C10—C14120.58 (17)C21—C22—H22119.9
C9—C10—C14120.82 (17)C22—C23—C24119.15 (17)
C12—C11—C10121.78 (17)C22—C23—H23120.4
C12—C11—H11119.1C24—C23—H23120.4
C10—C11—H11119.1C25—C24—C23120.34 (17)
C11—C12—C13118.06 (17)C25—C24—H24119.8
C11—C12—C15121.73 (17)C23—C24—H24119.8
C13—C12—C15120.21 (17)C24—C25—C20120.95 (17)
C8—C13—C12121.99 (17)C24—C25—H25119.5
C8—C13—H13119.0C20—C25—H25119.5
C12—C13—H13119.0
C2—N1—C1—O1179.48 (16)C7—C8—C9—C10177.55 (16)
C2—N1—C1—N20.4 (2)C8—C9—C10—C110.4 (3)
C4—N2—C1—O1179.83 (16)C8—C9—C10—C14178.39 (17)
C16—N2—C1—O14.8 (2)C9—C10—C11—C120.8 (3)
C4—N2—C1—N10.3 (2)C14—C10—C11—C12178.03 (17)
C16—N2—C1—N1175.32 (14)C10—C11—C12—C130.6 (3)
C1—N1—C2—O2178.90 (16)C10—C11—C12—C15179.97 (19)
C1—N1—C2—C30.5 (3)C9—C8—C13—C120.3 (3)
O2—C2—C3—C4179.46 (17)C7—C8—C13—C12177.79 (16)
N1—C2—C3—C40.1 (2)C11—C12—C13—C80.1 (3)
O2—C2—C3—C51.5 (2)C15—C12—C13—C8179.45 (18)
N1—C2—C3—C5179.14 (15)C17—O3—C16—N266.98 (18)
C2—C3—C4—N20.7 (2)C1—N2—C16—O3103.56 (17)
C5—C3—C4—N2179.69 (15)C4—N2—C16—O371.52 (19)
C2—C3—C4—C7178.51 (15)C16—O3—C17—C18163.75 (14)
C5—C3—C4—C70.5 (3)O3—C17—C18—C1970.60 (19)
C1—N2—C4—C30.9 (2)C17—C18—C19—C20179.67 (15)
C16—N2—C4—C3175.63 (15)C18—C19—C20—C2181.0 (2)
C1—N2—C4—C7178.43 (14)C18—C19—C20—C2597.2 (2)
C16—N2—C4—C73.6 (2)C25—C20—C21—C222.5 (3)
C4—C3—C5—C691.8 (2)C19—C20—C21—C22175.80 (17)
C2—C3—C5—C689.18 (19)C20—C21—C22—C231.0 (3)
C3—C4—C7—C8110.06 (19)C21—C22—C23—C241.3 (3)
N2—C4—C7—C870.7 (2)C22—C23—C24—C252.0 (3)
C4—C7—C8—C13141.21 (17)C23—C24—C25—C200.5 (3)
C4—C7—C8—C941.3 (2)C21—C20—C25—C241.7 (3)
C13—C8—C9—C100.1 (3)C19—C20—C25—C24176.55 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.89 (1)1.94 (1)2.826 (2)178 (2)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC25H30N2O3
Mr406.51
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)4.8276 (4), 14.9398 (10), 15.4574 (12)
α, β, γ (°)76.949 (6), 89.296 (6), 88.267 (6)
V3)1085.53 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.20 × 0.05
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.980, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
7623, 4974, 3719
Rint0.039
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.167, 1.04
No. of reflections4974
No. of parameters277
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.39, 0.29

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.89 (1)1.94 (1)2.826 (2)178 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, and the University of Malaya for supporting this study.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.  Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationEl-Brollosy, N. R., Al-Deeb, O. A., El-Emam, A. A., Pedersen, E. B., La Colla, P., Collu, G., Sanna, G. & Loddo, R. (2009). Arch. Pharm. Chem. Life Sci. 342, 663–670.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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