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

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ISSN: 2056-9890

1-Methyl-3-phenyl­quinoxalin-2(1H)-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bService commun Rayons X, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, 31062 Toulouse, France, cHétérochimie Fondamentale et Appliquée, Université Paul Sabatier, UMR 5069, 118 Route de Narbonne, 31062 Toulouse, France, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 24 August 2009; accepted 26 August 2009; online 5 September 2009)

The phenyl substituents in both independent mol­ecules of the title compound, C15H12N2O, are twisted with respect to the quinoxaline system [dihedral angles = 19.3 (1) and 30.4 (1)°].

Related literature

For the structure of 1-ethyl-3-methyl­quinoxalin-2(1H)-one, see: Benzeid et al. (2008[Benzeid, H., Vendier, L., Ramli, Y., Garrigues, B. & Essassi, E. M. (2008). Acta Cryst. E64, o2234.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O

  • Mr = 236.27

  • Monoclinic, P 21 /n

  • a = 16.3919 (5) Å

  • b = 7.0775 (2) Å

  • c = 20.0214 (6) Å

  • β = 95.434 (2)°

  • V = 2312.32 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 193 K

  • 0.60 × 0.20 × 0.10 mm

Data collection
  • Bruker APEX2 diffractometer

  • Absorption correction: none

  • 31360 measured reflections

  • 4682 independent reflections

  • 3068 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.114

  • S = 1.01

  • 4682 reflections

  • 327 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the structure of 1-ethyl-3-methylquinoxalin-2(1H)-one, see: Benzeid et al. (2008).

Experimental top

3-Phenylquinoxalin-2(1H)-one (1 g, 4.5 mmol), methyl iodide (0.31 ml, 5.0 mmol), potassium carbonate (0.7 g, 5.0 mmol) and a catalytic quantity of tetra-n-butylammonium bromide were stirred in N,N-dimethylformamide (20 ml) for 24 h. The mixture was filtered to remove the salts and the solvent removed under reduce pressure. The residue was recrystallized in ethanol to afford the pure compound in 80% yield.The formulation was established by proton and carbon-13 NMR spectroscopy in CDCl3.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2009).

Figures top
[Figure 1] Fig. 1. A thermal ellipsoid plot (Barbour, 2001) of the two unique molecules of C15H16N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
1-Methyl-3-phenylquinoxalin-2(1H)-one top
Crystal data top
C15H12N2OF(000) = 992
Mr = 236.27Dx = 1.357 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4338 reflections
a = 16.3919 (5) Åθ = 2.5–24.9°
b = 7.0775 (2) ŵ = 0.09 mm1
c = 20.0214 (6) ÅT = 193 K
β = 95.434 (2)°Plate, yellow
V = 2312.32 (12) Å30.60 × 0.20 × 0.10 mm
Z = 8
Data collection top
Bruker APEX2
diffractometer
3068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 26.4°, θmin = 5.2°
ϕ and ω scansh = 2020
31360 measured reflectionsk = 88
4682 independent reflectionsl = 2524
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0498P)2 + 0.4004P]
where P = (Fo2 + 2Fc2)/3
4682 reflections(Δ/σ)max = 0.001
327 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C15H12N2OV = 2312.32 (12) Å3
Mr = 236.27Z = 8
Monoclinic, P21/nMo Kα radiation
a = 16.3919 (5) ŵ = 0.09 mm1
b = 7.0775 (2) ÅT = 193 K
c = 20.0214 (6) Å0.60 × 0.20 × 0.10 mm
β = 95.434 (2)°
Data collection top
Bruker APEX2
diffractometer
3068 reflections with I > 2σ(I)
31360 measured reflectionsRint = 0.054
4682 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
4682 reflectionsΔρmin = 0.18 e Å3
327 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53417 (7)0.34744 (19)0.19948 (6)0.0472 (4)
O20.62711 (8)0.8355 (2)0.09382 (7)0.0632 (4)
N10.42018 (8)0.3190 (2)0.12599 (7)0.0323 (3)
N20.33162 (8)0.2202 (2)0.23283 (6)0.0326 (3)
N30.69753 (8)0.8664 (2)0.19620 (7)0.0358 (4)
N40.54955 (8)0.86008 (19)0.25385 (7)0.0317 (3)
C10.46011 (10)0.3149 (2)0.18965 (9)0.0331 (4)
C20.40856 (10)0.2669 (2)0.24408 (8)0.0300 (4)
C30.44373 (10)0.2670 (2)0.31523 (8)0.0309 (4)
C40.50477 (10)0.3928 (3)0.34009 (9)0.0389 (4)
H40.52810.47790.31050.047*
C50.53143 (11)0.3938 (3)0.40790 (9)0.0435 (5)
H50.57280.48020.42460.052*
C60.49836 (11)0.2705 (3)0.45122 (9)0.0453 (5)
H60.51690.27220.49760.054*
C70.43825 (11)0.1445 (3)0.42723 (9)0.0418 (5)
H70.41570.05900.45710.050*
C80.41091 (10)0.1428 (2)0.35977 (8)0.0364 (4)
H80.36940.05620.34350.044*
C90.46906 (12)0.3662 (3)0.07079 (9)0.0464 (5)
H9A0.45070.48760.05120.070*
H9B0.46220.26740.03640.070*
H9C0.52700.37510.08780.070*
C100.33732 (10)0.2762 (2)0.11315 (8)0.0306 (4)
C110.29496 (10)0.2221 (2)0.16767 (8)0.0309 (4)
C120.21273 (10)0.1659 (3)0.15667 (9)0.0382 (4)
H120.18440.12590.19350.046*
C130.17287 (11)0.1683 (3)0.09346 (9)0.0428 (5)
H130.11730.12910.08620.051*
C140.21443 (12)0.2287 (3)0.03988 (9)0.0438 (5)
H140.18630.23340.00380.053*
C150.29569 (11)0.2818 (2)0.04900 (8)0.0380 (4)
H150.32320.32210.01180.046*
C160.62597 (11)0.8499 (3)0.15482 (9)0.0382 (4)
C170.54917 (10)0.8488 (2)0.18917 (8)0.0309 (4)
C180.46772 (10)0.8295 (2)0.14974 (8)0.0312 (4)
C190.45321 (12)0.8707 (3)0.08144 (9)0.0407 (4)
H190.49690.91370.05730.049*
C200.37535 (13)0.8491 (3)0.04856 (10)0.0472 (5)
H200.36610.87800.00210.057*
C210.31130 (12)0.7860 (3)0.08274 (10)0.0469 (5)
H210.25840.76940.05970.056*
C220.32428 (11)0.7471 (3)0.15040 (10)0.0441 (5)
H220.28020.70510.17420.053*
C230.40153 (10)0.7693 (2)0.18359 (9)0.0369 (4)
H230.40980.74320.23030.044*
C240.77511 (11)0.8735 (3)0.16470 (10)0.0487 (5)
H24A0.76350.86990.11580.073*
H24B0.80910.76470.17950.073*
H24C0.80430.99050.17780.073*
C250.69876 (10)0.8736 (2)0.26575 (9)0.0341 (4)
C260.62318 (10)0.8714 (2)0.29362 (8)0.0314 (4)
C270.62170 (11)0.8786 (3)0.36323 (9)0.0402 (4)
H270.57070.87920.38210.048*
C280.69355 (12)0.8848 (3)0.40451 (10)0.0479 (5)
H280.69230.88900.45180.057*
C290.76810 (12)0.8850 (3)0.37677 (10)0.0499 (5)
H290.81760.88850.40550.060*
C300.77140 (11)0.8802 (3)0.30840 (10)0.0437 (5)
H300.82290.88130.29020.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0283 (7)0.0654 (9)0.0483 (8)0.0051 (6)0.0063 (6)0.0005 (7)
O20.0531 (9)0.1003 (13)0.0387 (8)0.0090 (8)0.0178 (7)0.0003 (8)
N10.0342 (8)0.0341 (8)0.0294 (8)0.0007 (6)0.0075 (6)0.0014 (6)
N20.0297 (8)0.0389 (8)0.0288 (8)0.0005 (7)0.0010 (6)0.0027 (6)
N30.0315 (8)0.0342 (8)0.0439 (9)0.0005 (7)0.0150 (7)0.0008 (7)
N40.0310 (7)0.0315 (8)0.0330 (8)0.0001 (6)0.0052 (6)0.0016 (6)
C10.0288 (9)0.0313 (9)0.0396 (10)0.0018 (7)0.0047 (8)0.0034 (8)
C20.0278 (9)0.0288 (9)0.0334 (9)0.0018 (7)0.0023 (7)0.0033 (7)
C30.0241 (8)0.0348 (9)0.0334 (9)0.0041 (7)0.0007 (7)0.0022 (8)
C40.0324 (9)0.0425 (11)0.0415 (11)0.0004 (8)0.0018 (8)0.0024 (8)
C50.0340 (10)0.0506 (12)0.0439 (11)0.0010 (9)0.0061 (8)0.0103 (9)
C60.0403 (11)0.0583 (13)0.0354 (10)0.0099 (10)0.0061 (8)0.0055 (10)
C70.0387 (10)0.0496 (12)0.0366 (10)0.0058 (9)0.0004 (8)0.0066 (9)
C80.0311 (9)0.0396 (10)0.0376 (10)0.0010 (8)0.0009 (8)0.0008 (8)
C90.0509 (11)0.0492 (12)0.0417 (11)0.0096 (10)0.0174 (9)0.0008 (9)
C100.0336 (9)0.0266 (9)0.0315 (9)0.0030 (7)0.0029 (7)0.0033 (7)
C110.0303 (9)0.0321 (9)0.0298 (9)0.0032 (7)0.0014 (7)0.0035 (7)
C120.0308 (9)0.0485 (11)0.0350 (10)0.0004 (8)0.0015 (8)0.0013 (8)
C130.0319 (10)0.0520 (12)0.0427 (11)0.0014 (9)0.0059 (8)0.0030 (9)
C140.0457 (11)0.0479 (12)0.0353 (10)0.0051 (9)0.0089 (9)0.0018 (9)
C150.0479 (11)0.0362 (10)0.0300 (9)0.0010 (9)0.0036 (8)0.0008 (8)
C160.0401 (10)0.0398 (11)0.0361 (10)0.0026 (8)0.0110 (8)0.0025 (8)
C170.0362 (9)0.0241 (9)0.0332 (10)0.0025 (7)0.0082 (7)0.0006 (7)
C180.0353 (9)0.0259 (9)0.0326 (9)0.0056 (7)0.0045 (7)0.0030 (7)
C190.0489 (11)0.0371 (10)0.0363 (10)0.0060 (9)0.0046 (9)0.0018 (8)
C200.0572 (13)0.0453 (12)0.0367 (10)0.0127 (10)0.0077 (10)0.0053 (9)
C210.0431 (11)0.0407 (11)0.0538 (13)0.0071 (9)0.0109 (10)0.0133 (9)
C220.0370 (10)0.0414 (11)0.0533 (12)0.0002 (9)0.0004 (9)0.0040 (9)
C230.0359 (10)0.0364 (10)0.0381 (10)0.0020 (8)0.0017 (8)0.0015 (8)
C240.0368 (10)0.0467 (12)0.0666 (13)0.0015 (9)0.0262 (10)0.0030 (10)
C250.0331 (9)0.0252 (9)0.0445 (10)0.0003 (7)0.0066 (8)0.0002 (8)
C260.0293 (9)0.0280 (9)0.0372 (10)0.0016 (7)0.0044 (7)0.0008 (7)
C270.0383 (10)0.0439 (11)0.0384 (10)0.0012 (9)0.0040 (8)0.0013 (8)
C280.0502 (12)0.0499 (12)0.0417 (11)0.0009 (10)0.0058 (9)0.0030 (9)
C290.0405 (11)0.0478 (12)0.0582 (13)0.0006 (9)0.0116 (10)0.0024 (10)
C300.0301 (10)0.0380 (11)0.0631 (13)0.0019 (8)0.0049 (9)0.0008 (9)
Geometric parameters (Å, º) top
O1—C11.2331 (19)C12—H120.9500
O2—C161.228 (2)C13—C141.391 (3)
N1—C11.377 (2)C13—H130.9500
N1—C101.392 (2)C14—C151.380 (2)
N1—C91.464 (2)C14—H140.9500
N2—C21.3027 (19)C15—H150.9500
N2—C111.384 (2)C16—C171.491 (2)
N3—C161.376 (2)C17—C181.491 (2)
N3—C251.392 (2)C18—C191.396 (2)
N3—C241.473 (2)C18—C231.399 (2)
N4—C171.297 (2)C19—C201.388 (3)
N4—C261.384 (2)C19—H190.9500
C1—C21.480 (2)C20—C211.381 (3)
C2—C31.485 (2)C20—H200.9500
C3—C41.395 (2)C21—C221.379 (3)
C3—C81.396 (2)C21—H210.9500
C4—C51.386 (2)C22—C231.382 (2)
C4—H40.9500C22—H220.9500
C5—C61.377 (3)C23—H230.9500
C5—H50.9500C24—H24A0.9800
C6—C71.381 (3)C24—H24B0.9800
C6—H60.9500C24—H24C0.9800
C7—C81.382 (2)C25—C301.399 (2)
C7—H70.9500C25—C261.406 (2)
C8—H80.9500C26—C271.397 (2)
C9—H9A0.9800C27—C281.374 (2)
C9—H9B0.9800C27—H270.9500
C9—H9C0.9800C28—C291.389 (3)
C10—C151.397 (2)C28—H280.9500
C10—C111.401 (2)C29—C301.376 (3)
C11—C121.402 (2)C29—H290.9500
C12—C131.368 (2)C30—H300.9500
C1—N1—C10122.44 (14)C13—C14—H14119.4
C1—N1—C9117.23 (14)C14—C15—C10119.70 (17)
C10—N1—C9120.31 (14)C14—C15—H15120.1
C2—N2—C11119.18 (14)C10—C15—H15120.1
C16—N3—C25122.45 (14)O2—C16—N3120.92 (16)
C16—N3—C24117.81 (15)O2—C16—C17123.49 (16)
C25—N3—C24119.73 (15)N3—C16—C17115.58 (15)
C17—N4—C26119.98 (14)N4—C17—C16122.41 (15)
O1—C1—N1121.22 (15)N4—C17—C18116.98 (15)
O1—C1—C2123.17 (16)C16—C17—C18120.59 (15)
N1—C1—C2115.60 (14)C19—C18—C23118.03 (16)
N2—C2—C1122.79 (15)C19—C18—C17124.07 (16)
N2—C2—C3116.58 (14)C23—C18—C17117.89 (15)
C1—C2—C3120.62 (14)C20—C19—C18120.34 (18)
C4—C3—C8118.73 (15)C20—C19—H19119.8
C4—C3—C2122.86 (15)C18—C19—H19119.8
C8—C3—C2118.31 (15)C21—C20—C19120.59 (18)
C5—C4—C3120.11 (17)C21—C20—H20119.7
C5—C4—H4119.9C19—C20—H20119.7
C3—C4—H4119.9C22—C21—C20119.84 (18)
C6—C5—C4120.47 (18)C22—C21—H21120.1
C6—C5—H5119.8C20—C21—H21120.1
C4—C5—H5119.8C21—C22—C23119.92 (19)
C5—C6—C7120.04 (17)C21—C22—H22120.0
C5—C6—H6120.0C23—C22—H22120.0
C7—C6—H6120.0C22—C23—C18121.26 (17)
C6—C7—C8120.00 (18)C22—C23—H23119.4
C6—C7—H7120.0C18—C23—H23119.4
C8—C7—H7120.0N3—C24—H24A109.5
C7—C8—C3120.65 (16)N3—C24—H24B109.5
C7—C8—H8119.7H24A—C24—H24B109.5
C3—C8—H8119.7N3—C24—H24C109.5
N1—C9—H9A109.5H24A—C24—H24C109.5
N1—C9—H9B109.5H24B—C24—H24C109.5
H9A—C9—H9B109.5N3—C25—C30122.88 (16)
N1—C9—H9C109.5N3—C25—C26117.83 (15)
H9A—C9—H9C109.5C30—C25—C26119.28 (17)
H9B—C9—H9C109.5N4—C26—C27118.65 (15)
N1—C10—C15123.16 (15)N4—C26—C25121.70 (15)
N1—C10—C11117.56 (14)C27—C26—C25119.65 (16)
C15—C10—C11119.28 (16)C28—C27—C26120.42 (17)
N2—C11—C10122.27 (15)C28—C27—H27119.8
N2—C11—C12118.07 (15)C26—C27—H27119.8
C10—C11—C12119.66 (15)C27—C28—C29119.73 (18)
C13—C12—C11120.63 (17)C27—C28—H28120.1
C13—C12—H12119.7C29—C28—H28120.1
C11—C12—H12119.7C30—C29—C28121.12 (18)
C12—C13—C14119.40 (17)C30—C29—H29119.4
C12—C13—H13120.3C28—C29—H29119.4
C14—C13—H13120.3C29—C30—C25119.79 (17)
C15—C14—C13121.25 (17)C29—C30—H30120.1
C15—C14—H14119.4C25—C30—H30120.1
C10—N1—C1—O1177.65 (15)C25—N3—C16—O2176.73 (17)
C9—N1—C1—O10.8 (2)C24—N3—C16—O22.3 (3)
C10—N1—C1—C21.6 (2)C25—N3—C16—C172.6 (2)
C9—N1—C1—C2179.90 (15)C24—N3—C16—C17178.34 (15)
C11—N2—C2—C12.6 (2)C26—N4—C17—C160.8 (2)
C11—N2—C2—C3178.43 (14)C26—N4—C17—C18177.68 (14)
O1—C1—C2—N2175.20 (16)O2—C16—C17—N4178.43 (17)
N1—C1—C2—N24.1 (2)N3—C16—C17—N40.9 (2)
O1—C1—C2—C33.7 (3)O2—C16—C17—C180.0 (3)
N1—C1—C2—C3177.04 (14)N3—C16—C17—C18179.32 (14)
N2—C2—C3—C4147.10 (16)N4—C17—C18—C19160.36 (16)
C1—C2—C3—C433.9 (2)C16—C17—C18—C1921.2 (2)
N2—C2—C3—C829.2 (2)N4—C17—C18—C2318.6 (2)
C1—C2—C3—C8149.75 (16)C16—C17—C18—C23159.91 (15)
C8—C3—C4—C50.4 (3)C23—C18—C19—C200.9 (2)
C2—C3—C4—C5175.90 (16)C17—C18—C19—C20179.88 (16)
C3—C4—C5—C60.3 (3)C18—C19—C20—C210.3 (3)
C4—C5—C6—C70.1 (3)C19—C20—C21—C221.2 (3)
C5—C6—C7—C80.4 (3)C20—C21—C22—C230.8 (3)
C6—C7—C8—C30.3 (3)C21—C22—C23—C180.5 (3)
C4—C3—C8—C70.1 (3)C19—C18—C23—C221.3 (3)
C2—C3—C8—C7176.37 (15)C17—C18—C23—C22179.67 (15)
C1—N1—C10—C15179.25 (15)C16—N3—C25—C30176.49 (16)
C9—N1—C10—C152.3 (2)C24—N3—C25—C302.5 (2)
C1—N1—C10—C111.9 (2)C16—N3—C25—C262.6 (2)
C9—N1—C10—C11176.53 (15)C24—N3—C25—C26178.38 (15)
C2—N2—C11—C101.3 (2)C17—N4—C26—C27178.43 (16)
C2—N2—C11—C12178.21 (15)C17—N4—C26—C250.9 (2)
N1—C10—C11—N23.5 (2)N3—C25—C26—N40.8 (2)
C15—C10—C11—N2177.55 (15)C30—C25—C26—N4178.34 (15)
N1—C10—C11—C12175.94 (15)N3—C25—C26—C27179.93 (16)
C15—C10—C11—C123.0 (2)C30—C25—C26—C270.9 (2)
N2—C11—C12—C13178.77 (16)N4—C26—C27—C28178.28 (16)
C10—C11—C12—C131.7 (3)C25—C26—C27—C281.0 (3)
C11—C12—C13—C140.6 (3)C26—C27—C28—C290.4 (3)
C12—C13—C14—C151.6 (3)C27—C28—C29—C300.4 (3)
C13—C14—C15—C100.3 (3)C28—C29—C30—C250.5 (3)
N1—C10—C15—C14176.88 (16)N3—C25—C30—C29179.29 (17)
C11—C10—C15—C142.0 (2)C26—C25—C30—C290.2 (3)

Experimental details

Crystal data
Chemical formulaC15H12N2O
Mr236.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)193
a, b, c (Å)16.3919 (5), 7.0775 (2), 20.0214 (6)
β (°) 95.434 (2)
V3)2312.32 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.60 × 0.20 × 0.10
Data collection
DiffractometerBruker APEX2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
31360, 4682, 3068
Rint0.054
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.114, 1.01
No. of reflections4682
No. of parameters327
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.18

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBenzeid, H., Vendier, L., Ramli, Y., Garrigues, B. & Essassi, E. M. (2008). Acta Cryst. E64, o2234.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  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. (2009). publCIF. In preparation.  Google Scholar

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