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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1235

3-{2-[(3-Phenyl­quinoxalin-2-yl)­­oxy]ethyl}-1,3-oxazolidin-2-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bService de Radiocristallographie, Institut de Chimie UMR 7177, CNRS-UdS Tour de Chimie, Rez-de-chaussée 1 rue Blaise Pascal, BP 296/R867008, Strasbourg Cedex, France, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 April 2011; accepted 19 April 2011; online 29 April 2011)

The asymmetric unit of the title compound, C19H17N3O3, consists of two independent mol­ecules that are disposed about a pseudo-centre of inversion. The plane of the phenyl substituent is twisted by 38.1 (1)° [43.6 (1)° in the second mol­ecule] out of the plane of the quinoxaline ring system. The five-membered ring of the substituent at the 2-position adopts an envelope conformation; the 5-CH2 atom representing the flap lies out of the plane defined by the other four atoms [deviation 0.264 (7) Å in the first mol­ecule and 0.291 (6) Å in the second]. The dihedral angle between the five-membered ring and the 4-phenyl ring is 84.9 (1)° while that between the five-membered ring and the 5-phenyl ring is 65.6 (1)°.

Related literature

For the crystal structure of 3-[2-(3-methyl­quinoxalin-2-yl­oxy)eth­yl]-1,3-oxazolidin-2-one, see: Ahoya et al. (2010[Ahoya, C. A., Bouhfid, R., Daouda, B., Essassi, E. M. & El Ammari, L. (2010). Acta Cryst. E66, o1050.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17N3O3

  • Mr = 335.36

  • Orthorhombic, P c a 21

  • a = 10.1392 (4) Å

  • b = 9.1398 (4) Å

  • c = 34.8462 (15) Å

  • V = 3229.2 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 173 K

  • 0.40 × 0.35 × 0.30 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • 25550 measured reflections

  • 4767 independent reflections

  • 4101 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.123

  • S = 1.03

  • 4767 reflections

  • 451 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: 4149 Friedel pairs merged

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

A recent study reports the crystal structure of 3-[2-(3-methylquinoxalin-2-yloxy)ethyl]-1,3-oxazolidin-2-one (Ahoya et al., 2010). The present study reports the 3-phenyl analog (Scheme I). The asymmetric unit consists of two independent molecules that are disposed about a pseudo center-of-inversion (Fig. 1). The phenyl substituent of the 3-position of the quinoxaline ring is twisted by 38.1 (1)° [43.6 (1)° in the second molecule]. The five-membering ring of the substituent at the 2-position adopts the shape of an envelope; the 5-CH2 atom representing the flap lies out of the plane defined by the other four atoms [deviation 0.264 (7) Å in the first molecule and 0.291 (6) Å in the second molecule].

Related literature top

For the crystal structure of 3-[2-(3-methylquinoxalin-2-yloxy)ethyl]-1,3-oxazolidin-2-one, see: Ahoya et al. (2010).

Experimental top

3-Phenyl-quinoxalin-2-one (1.25 mmol, 0.28 g), di(chloroethyl)amine hydrochloride (2.66 mmol, 0.50 g), potassium carbonate (4.00 mmol, 0.52 g) and tetra-n-butylammonium bromide (0.01 mmol, 0.003 g) were heated in DMF (40 ml); the progress of the reaction was monitored by thin layer chromatography. On completion, the solvent was removed under reduced pressure and the residue was chromatographed on silica column (n-hexane/ethyl acetate:4/6). Recrystallization was effected by using the sample solvent system.

Refinement top

H atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C); 4149 Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of two independent molecules of C19H17N3O3 disposed about a pseudo center-of-inversion at the 70% probability level; H atoms are drawn as arbitrary radius.
3-{2-[(3-Phenylquinoxalin-2-yl)oxy]ethyl}-1,3-oxazolidin-2-one top
Crystal data top
C19H17N3O3F(000) = 1408
Mr = 335.36Dx = 1.380 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 9872 reflections
a = 10.1392 (4) Åθ = 2.3–30.0°
b = 9.1398 (4) ŵ = 0.10 mm1
c = 34.8462 (15) ÅT = 173 K
V = 3229.2 (2) Å3Prism, colourless
Z = 80.40 × 0.35 × 0.30 mm
Data collection top
Bruker X8 APEXII
diffractometer
4101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 30.0°, θmin = 2.5°
ϕ and ω scansh = 1414
25550 measured reflectionsk = 1212
4767 independent reflectionsl = 4947
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0525P)2 + 1.9526P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4767 reflectionsΔρmax = 0.32 e Å3
451 parametersΔρmin = 0.21 e Å3
1 restraintAbsolute structure: 4149 Friedel pairs merged
Primary atom site location: structure-invariant direct methods
Crystal data top
C19H17N3O3V = 3229.2 (2) Å3
Mr = 335.36Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 10.1392 (4) ŵ = 0.10 mm1
b = 9.1398 (4) ÅT = 173 K
c = 34.8462 (15) Å0.40 × 0.35 × 0.30 mm
Data collection top
Bruker X8 APEXII
diffractometer
4101 reflections with I > 2σ(I)
25550 measured reflectionsRint = 0.029
4767 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0471 restraint
wR(F2) = 0.123H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å3
4767 reflectionsΔρmin = 0.21 e Å3
451 parametersAbsolute structure: 4149 Friedel pairs merged
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3755 (2)0.6241 (2)0.49991 (7)0.0238 (4)
O20.1310 (2)0.3976 (3)0.55878 (9)0.0433 (6)
O30.2900 (3)0.3586 (3)0.60256 (7)0.0380 (6)
O40.3780 (2)0.8711 (2)0.79097 (7)0.0236 (5)
O50.6231 (2)1.1037 (3)0.73247 (9)0.0426 (6)
O60.4633 (2)1.1405 (3)0.68853 (7)0.0378 (6)
N10.5295 (2)0.7359 (3)0.46162 (7)0.0231 (5)
N20.4634 (3)1.0015 (3)0.49854 (11)0.0229 (7)
N30.3471 (2)0.3614 (3)0.54162 (8)0.0251 (5)
N40.2237 (2)0.7592 (3)0.82911 (7)0.0218 (5)
N50.2891 (3)0.4944 (3)0.79247 (12)0.0257 (7)
N60.4059 (2)1.1361 (3)0.74966 (8)0.0233 (5)
C10.5889 (3)0.8656 (4)0.45148 (9)0.0238 (7)
C20.6894 (3)0.8632 (4)0.42211 (8)0.0264 (7)
H20.71620.77390.41050.032*
C30.7450 (5)0.9938 (4)0.41148 (15)0.0316 (10)
H30.81220.99310.39250.038*
C40.7080 (3)1.1262 (5)0.42711 (10)0.0307 (8)
H40.74661.21470.41830.037*
C50.6123 (4)1.1283 (4)0.45641 (10)0.0293 (7)
H50.58761.21800.46810.035*
C60.5546 (3)0.9977 (3)0.46791 (10)0.0232 (8)
C70.4435 (3)0.7436 (3)0.48952 (8)0.0208 (5)
C80.4129 (2)0.8775 (3)0.50968 (8)0.0205 (5)
C90.3280 (3)0.8803 (3)0.54447 (8)0.0221 (5)
C100.3353 (3)0.7709 (4)0.57228 (8)0.0268 (6)
H100.38930.68750.56810.032*
C110.2637 (3)0.7835 (4)0.60623 (9)0.0333 (7)
H110.26880.70880.62510.040*
C120.1847 (3)0.9053 (4)0.61239 (9)0.0354 (8)
H120.13760.91540.63580.042*
C130.1748 (4)1.0128 (4)0.58411 (14)0.0321 (9)
H130.11691.09350.58750.038*
C140.2494 (5)1.0014 (3)0.55127 (15)0.0298 (10)
H140.24691.07810.53290.036*
C150.4161 (4)0.4879 (3)0.48313 (12)0.0251 (8)
H15A0.51030.46890.48880.030*
H15B0.40440.49070.45490.030*
C160.3308 (3)0.3702 (4)0.50051 (10)0.0271 (7)
H16A0.23720.39070.49450.033*
H16B0.35390.27470.48890.033*
C170.2459 (3)0.3749 (3)0.56612 (10)0.0295 (6)
C180.4324 (4)0.3412 (6)0.60200 (11)0.0493 (10)
H18A0.45970.25880.61860.059*
H18B0.47660.43150.61090.059*
C190.4661 (3)0.3101 (4)0.56046 (9)0.0269 (6)
H19A0.54470.36570.55200.032*
H19B0.48080.20440.55590.032*
C200.1637 (3)0.6307 (4)0.84002 (9)0.0209 (6)
C210.0673 (3)0.6295 (4)0.86756 (11)0.0289 (7)
H210.04130.71940.87900.035*
C220.0066 (5)0.5014 (4)0.87928 (13)0.0317 (11)
H220.05900.50170.89880.038*
C230.0464 (4)0.3684 (4)0.86090 (11)0.0327 (8)
H230.00460.27950.86810.039*
C240.1396 (4)0.3652 (4)0.83418 (13)0.0319 (8)
H240.16460.27420.82320.038*
C250.2034 (4)0.4973 (3)0.82158 (12)0.0237 (8)
C260.3085 (3)0.7517 (3)0.80137 (8)0.0205 (5)
C270.3400 (3)0.6188 (3)0.78065 (8)0.0215 (5)
C280.4249 (3)0.6163 (3)0.74596 (8)0.0216 (5)
C290.4178 (3)0.7269 (4)0.71840 (9)0.0277 (6)
H290.36360.81020.72270.033*
C300.4903 (3)0.7147 (4)0.68470 (9)0.0333 (7)
H300.48520.78970.66590.040*
C310.5706 (3)0.5932 (4)0.67837 (10)0.0352 (7)
H310.61950.58550.65520.042*
C320.5793 (5)0.4847 (4)0.70545 (15)0.0358 (10)
H320.63360.40170.70090.043*
C330.5080 (4)0.4961 (3)0.73990 (14)0.0237 (9)
H330.51620.42250.75900.028*
C340.3381 (4)1.0076 (3)0.80828 (14)0.0258 (8)
H34A0.35161.00420.83640.031*
H34B0.24351.02650.80320.031*
C350.4223 (3)1.1268 (3)0.79058 (9)0.0225 (6)
H35A0.39871.22200.80230.027*
H35B0.51621.10720.79650.027*
C360.5075 (3)1.1237 (3)0.72500 (10)0.0283 (6)
C370.3211 (4)1.1544 (5)0.68928 (11)0.0441 (9)
H37A0.27871.06230.68080.053*
H37B0.29181.23470.67220.053*
C380.2867 (3)1.1876 (3)0.73069 (9)0.0264 (6)
H38A0.27241.29360.73490.032*
H38B0.20781.13270.73920.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0227 (10)0.0214 (10)0.0272 (10)0.0002 (9)0.0067 (8)0.0008 (8)
O20.0246 (10)0.0476 (15)0.0577 (16)0.0079 (10)0.0092 (11)0.0058 (13)
O30.0388 (13)0.0437 (14)0.0314 (12)0.0074 (11)0.0109 (10)0.0041 (11)
O40.0293 (11)0.0163 (9)0.0252 (10)0.0016 (8)0.0032 (9)0.0011 (8)
O50.0239 (11)0.0443 (14)0.0596 (17)0.0070 (10)0.0094 (11)0.0058 (13)
O60.0382 (13)0.0409 (14)0.0342 (12)0.0083 (11)0.0118 (10)0.0039 (11)
N10.0240 (10)0.0263 (12)0.0190 (10)0.0006 (9)0.0022 (8)0.0018 (9)
N20.0232 (16)0.0223 (15)0.0231 (15)0.0025 (8)0.0064 (13)0.0012 (9)
N30.0206 (10)0.0283 (13)0.0263 (12)0.0009 (9)0.0006 (9)0.0047 (10)
N40.0238 (11)0.0215 (11)0.0201 (10)0.0001 (9)0.0031 (8)0.0013 (9)
N50.0267 (17)0.0215 (16)0.0289 (17)0.0000 (9)0.0015 (14)0.0010 (9)
N60.0191 (10)0.0226 (11)0.0281 (12)0.0002 (9)0.0021 (9)0.0030 (10)
C10.0219 (13)0.0323 (17)0.0173 (12)0.0003 (12)0.0013 (10)0.0039 (12)
C20.0294 (14)0.0388 (18)0.0109 (11)0.0004 (13)0.0079 (11)0.0013 (12)
C30.029 (2)0.041 (3)0.026 (2)0.0077 (12)0.0040 (16)0.0064 (12)
C40.0256 (15)0.0408 (19)0.0256 (15)0.0087 (14)0.0061 (12)0.0095 (14)
C50.0314 (16)0.0314 (17)0.0251 (15)0.0041 (14)0.0011 (12)0.0051 (14)
C60.0150 (13)0.041 (2)0.0132 (14)0.0022 (10)0.0051 (12)0.0045 (10)
C70.0210 (11)0.0216 (13)0.0199 (12)0.0006 (10)0.0003 (9)0.0022 (10)
C80.0177 (11)0.0246 (13)0.0191 (11)0.0001 (10)0.0002 (9)0.0003 (10)
C90.0193 (11)0.0236 (13)0.0234 (12)0.0032 (10)0.0016 (9)0.0031 (11)
C100.0263 (13)0.0334 (15)0.0207 (12)0.0014 (12)0.0007 (10)0.0001 (12)
C110.0333 (15)0.0439 (18)0.0227 (13)0.0083 (14)0.0002 (11)0.0020 (14)
C120.0290 (15)0.052 (2)0.0250 (14)0.0129 (14)0.0094 (12)0.0111 (14)
C130.0248 (17)0.0318 (18)0.040 (2)0.0047 (12)0.0084 (16)0.0117 (14)
C140.0236 (17)0.032 (2)0.034 (3)0.0045 (11)0.0093 (15)0.0036 (12)
C150.035 (2)0.0204 (16)0.0197 (17)0.0014 (11)0.0060 (14)0.0005 (10)
C160.0282 (15)0.0248 (15)0.0283 (14)0.0025 (12)0.0027 (12)0.0000 (13)
C170.0297 (14)0.0204 (13)0.0384 (16)0.0025 (12)0.0078 (12)0.0047 (13)
C180.0375 (18)0.082 (3)0.0287 (17)0.0145 (19)0.0006 (14)0.0080 (19)
C190.0222 (12)0.0308 (15)0.0278 (13)0.0016 (11)0.0015 (11)0.0009 (12)
C200.0219 (13)0.0229 (14)0.0180 (12)0.0011 (11)0.0073 (10)0.0006 (11)
C210.0255 (14)0.0301 (16)0.0311 (16)0.0009 (13)0.0028 (12)0.0037 (14)
C220.027 (2)0.051 (3)0.0172 (18)0.0041 (13)0.0003 (14)0.0041 (12)
C230.0376 (17)0.0300 (17)0.0305 (17)0.0089 (14)0.0037 (14)0.0071 (15)
C240.0309 (16)0.0213 (16)0.043 (2)0.0030 (13)0.0021 (14)0.0012 (15)
C250.0278 (17)0.0116 (14)0.032 (2)0.0009 (9)0.0067 (15)0.0007 (9)
C260.0214 (11)0.0179 (12)0.0223 (12)0.0000 (10)0.0047 (9)0.0006 (10)
C270.0219 (12)0.0196 (12)0.0229 (12)0.0001 (10)0.0015 (9)0.0013 (10)
C280.0194 (11)0.0249 (13)0.0205 (12)0.0026 (10)0.0016 (9)0.0041 (11)
C290.0263 (13)0.0281 (14)0.0287 (14)0.0001 (12)0.0017 (11)0.0003 (12)
C300.0342 (15)0.0446 (19)0.0210 (13)0.0078 (14)0.0007 (11)0.0033 (14)
C310.0323 (16)0.046 (2)0.0279 (15)0.0129 (14)0.0085 (12)0.0145 (14)
C320.0286 (19)0.0362 (19)0.043 (2)0.0036 (14)0.0104 (18)0.0176 (16)
C330.0234 (17)0.0167 (16)0.031 (2)0.0016 (9)0.0030 (14)0.0027 (10)
C340.0269 (18)0.0196 (16)0.0310 (19)0.0011 (10)0.0013 (15)0.0046 (11)
C350.0219 (13)0.0165 (12)0.0290 (14)0.0025 (11)0.0013 (11)0.0021 (11)
C360.0278 (14)0.0212 (13)0.0358 (16)0.0032 (11)0.0082 (12)0.0026 (12)
C370.0394 (18)0.064 (3)0.0284 (16)0.0063 (17)0.0006 (14)0.0040 (17)
C380.0216 (12)0.0284 (14)0.0293 (14)0.0007 (11)0.0016 (11)0.0013 (12)
Geometric parameters (Å, º) top
O1—C71.342 (3)C13—H130.9500
O1—C151.436 (4)C14—H140.9500
O2—C171.210 (4)C15—C161.508 (5)
O3—C171.355 (4)C15—H15A0.9900
O3—C181.452 (5)C15—H15B0.9900
O4—C261.349 (4)C16—H16A0.9900
O4—C341.444 (4)C16—H16B0.9900
O5—C361.214 (4)C18—C191.514 (5)
O6—C361.356 (4)C18—H18A0.9900
O6—C371.448 (4)C18—H18B0.9900
N1—C71.308 (4)C19—H19A0.9900
N1—C11.376 (4)C19—H19B0.9900
N2—C81.303 (4)C20—C211.370 (5)
N2—C61.413 (5)C20—C251.436 (5)
N3—C171.341 (4)C21—C221.385 (5)
N3—C161.444 (4)C21—H210.9500
N3—C191.451 (4)C22—C231.432 (6)
N4—C261.295 (4)C22—H220.9500
N4—C201.376 (4)C23—C241.327 (6)
N5—C271.316 (4)C23—H230.9500
N5—C251.336 (5)C24—C251.438 (5)
N6—C361.347 (4)C24—H240.9500
N6—C351.438 (4)C26—C271.448 (4)
N6—C381.456 (4)C27—C281.484 (4)
C1—C61.380 (5)C28—C291.397 (4)
C1—C21.445 (4)C28—C331.401 (4)
C2—C31.372 (5)C29—C301.390 (4)
C2—H20.9500C29—H290.9500
C3—C41.379 (6)C30—C311.395 (5)
C3—H30.9500C30—H300.9500
C4—C51.409 (5)C31—C321.372 (6)
C4—H40.9500C31—H310.9500
C5—C61.389 (5)C32—C331.405 (7)
C5—H50.9500C32—H320.9500
C7—C81.445 (4)C33—H330.9500
C8—C91.487 (4)C34—C351.515 (5)
C9—C141.385 (5)C34—H34A0.9900
C9—C101.394 (4)C34—H34B0.9900
C10—C111.393 (4)C35—H35A0.9900
C10—H100.9500C35—H35B0.9900
C11—C121.388 (5)C37—C381.515 (5)
C11—H110.9500C37—H37A0.9900
C12—C131.396 (6)C37—H37B0.9900
C12—H120.9500C38—H38A0.9900
C13—C141.375 (7)C38—H38B0.9900
C7—O1—C15116.6 (2)H18A—C18—H18B108.8
C17—O3—C18109.1 (3)N3—C19—C18100.6 (3)
C26—O4—C34116.1 (3)N3—C19—H19A111.7
C36—O6—C37108.8 (2)C18—C19—H19A111.7
C7—N1—C1115.8 (3)N3—C19—H19B111.7
C8—N2—C6117.4 (3)C18—C19—H19B111.7
C17—N3—C16122.6 (3)H19A—C19—H19B109.4
C17—N3—C19112.2 (3)C21—C20—N4121.0 (3)
C16—N3—C19124.2 (3)C21—C20—C25120.4 (3)
C26—N4—C20117.0 (3)N4—C20—C25118.5 (3)
C27—N5—C25118.4 (3)C20—C21—C22122.1 (4)
C36—N6—C35122.6 (3)C20—C21—H21119.0
C36—N6—C38111.9 (3)C22—C21—H21119.0
C35—N6—C38124.4 (2)C21—C22—C23117.4 (4)
N1—C1—C6122.5 (3)C21—C22—H22121.3
N1—C1—C2118.5 (3)C23—C22—H22121.3
C6—C1—C2119.0 (3)C24—C23—C22122.2 (4)
C3—C2—C1117.9 (4)C24—C23—H23118.9
C3—C2—H2121.0C22—C23—H23118.9
C1—C2—H2121.0C23—C24—C25121.0 (4)
C2—C3—C4123.0 (4)C23—C24—H24119.5
C2—C3—H3118.5C25—C24—H24119.5
C4—C3—H3118.5N5—C25—C20122.6 (3)
C3—C4—C5119.1 (4)N5—C25—C24120.5 (3)
C3—C4—H4120.5C20—C25—C24116.8 (4)
C5—C4—H4120.5N4—C26—O4120.3 (3)
C6—C5—C4119.2 (4)N4—C26—C27124.3 (3)
C6—C5—H5120.4O4—C26—C27115.4 (2)
C4—C5—H5120.4N5—C27—C26118.8 (3)
C1—C6—C5121.7 (3)N5—C27—C28118.0 (3)
C1—C6—N2120.0 (3)C26—C27—C28123.2 (3)
C5—C6—N2118.2 (3)C29—C28—C33119.7 (3)
N1—C7—O1120.0 (3)C29—C28—C27121.2 (3)
N1—C7—C8123.4 (3)C33—C28—C27119.0 (3)
O1—C7—C8116.6 (2)C30—C29—C28119.7 (3)
N2—C8—C7120.5 (3)C30—C29—H29120.1
N2—C8—C9117.1 (3)C28—C29—H29120.1
C7—C8—C9122.4 (2)C29—C30—C31120.4 (3)
C14—C9—C10119.0 (3)C29—C30—H30119.8
C14—C9—C8119.1 (3)C31—C30—H30119.8
C10—C9—C8121.6 (3)C32—C31—C30120.3 (3)
C9—C10—C11120.2 (3)C32—C31—H31119.9
C9—C10—H10119.9C30—C31—H31119.9
C11—C10—H10119.9C31—C32—C33120.1 (4)
C12—C11—C10119.9 (3)C31—C32—H32120.0
C12—C11—H11120.1C33—C32—H32120.0
C10—C11—H11120.1C28—C33—C32119.8 (4)
C11—C12—C13119.8 (3)C28—C33—H33120.1
C11—C12—H12120.1C32—C33—H33120.1
C13—C12—H12120.1O4—C34—C35107.0 (3)
C14—C13—C12119.6 (4)O4—C34—H34A110.3
C14—C13—H13120.2C35—C34—H34A110.3
C12—C13—H13120.2O4—C34—H34B110.3
C13—C14—C9121.3 (4)C35—C34—H34B110.3
C13—C14—H14119.3H34A—C34—H34B108.6
C9—C14—H14119.3N6—C35—C34112.4 (3)
O1—C15—C16106.9 (3)N6—C35—H35A109.1
O1—C15—H15A110.3C34—C35—H35A109.1
C16—C15—H15A110.3N6—C35—H35B109.1
O1—C15—H15B110.3C34—C35—H35B109.1
C16—C15—H15B110.3H35A—C35—H35B107.9
H15A—C15—H15B108.6O5—C36—N6127.9 (3)
N3—C16—C15111.9 (3)O5—C36—O6122.5 (3)
N3—C16—H16A109.2N6—C36—O6109.6 (3)
C15—C16—H16A109.2O6—C37—C38105.3 (3)
N3—C16—H16B109.2O6—C37—H37A110.7
C15—C16—H16B109.2C38—C37—H37A110.7
H16A—C16—H16B107.9O6—C37—H37B110.7
O2—C17—N3128.2 (3)C38—C37—H37B110.7
O2—C17—O3122.3 (3)H37A—C37—H37B108.8
N3—C17—O3109.5 (3)N6—C38—C37100.1 (3)
O3—C18—C19105.0 (3)N6—C38—H38A111.7
O3—C18—H18A110.8C37—C38—H38A111.7
C19—C18—H18A110.8N6—C38—H38B111.7
O3—C18—H18B110.8C37—C38—H38B111.7
C19—C18—H18B110.8H38A—C38—H38B109.5
C7—N1—C1—C63.9 (5)C26—N4—C20—C21176.2 (3)
C7—N1—C1—C2177.0 (3)C26—N4—C20—C253.1 (4)
N1—C1—C2—C3178.1 (4)N4—C20—C21—C22179.3 (3)
C6—C1—C2—C31.0 (5)C25—C20—C21—C221.4 (5)
C1—C2—C3—C40.9 (7)C20—C21—C22—C231.2 (6)
C2—C3—C4—C52.5 (7)C21—C22—C23—C241.4 (6)
C3—C4—C5—C62.1 (5)C22—C23—C24—C251.6 (6)
N1—C1—C6—C5177.8 (3)C27—N5—C25—C200.8 (5)
C2—C1—C6—C51.3 (5)C27—N5—C25—C24176.6 (4)
N1—C1—C6—N25.4 (5)C21—C20—C25—N5174.5 (3)
C2—C1—C6—N2175.5 (3)N4—C20—C25—N54.9 (5)
C4—C5—C6—C10.2 (5)C21—C20—C25—C241.5 (5)
C4—C5—C6—N2177.1 (3)N4—C20—C25—C24179.2 (3)
C8—N2—C6—C11.2 (5)C23—C24—C25—N5174.4 (4)
C8—N2—C6—C5178.1 (4)C23—C24—C25—C201.7 (6)
C1—N1—C7—O1176.3 (3)C20—N4—C26—O4175.3 (3)
C1—N1—C7—C81.5 (4)C20—N4—C26—C272.2 (4)
C15—O1—C7—N19.0 (4)C34—O4—C26—N48.9 (4)
C15—O1—C7—C8173.0 (3)C34—O4—C26—C27173.4 (3)
C6—N2—C8—C74.0 (5)C25—N5—C27—C264.4 (5)
C6—N2—C8—C9173.8 (3)C25—N5—C27—C28174.2 (3)
N1—C7—C8—N25.7 (4)N4—C26—C27—N56.3 (5)
O1—C7—C8—N2172.3 (3)O4—C26—C27—N5171.2 (3)
N1—C7—C8—C9172.0 (3)N4—C26—C27—C28172.2 (3)
O1—C7—C8—C910.1 (4)O4—C26—C27—C2810.2 (4)
N2—C8—C9—C1434.6 (4)N5—C27—C28—C29140.0 (3)
C7—C8—C9—C14147.7 (3)C26—C27—C28—C2938.6 (4)
N2—C8—C9—C10138.9 (3)N5—C27—C28—C3336.4 (4)
C7—C8—C9—C1038.8 (4)C26—C27—C28—C33145.1 (3)
C14—C9—C10—C110.4 (5)C33—C28—C29—C301.8 (5)
C8—C9—C10—C11173.9 (3)C27—C28—C29—C30174.4 (3)
C9—C10—C11—C120.0 (5)C28—C29—C30—C310.4 (5)
C10—C11—C12—C131.7 (5)C29—C30—C31—C320.3 (5)
C11—C12—C13—C143.8 (6)C30—C31—C32—C330.5 (6)
C12—C13—C14—C94.3 (7)C29—C28—C33—C322.7 (5)
C10—C9—C14—C132.6 (6)C27—C28—C33—C32173.7 (3)
C8—C9—C14—C13176.3 (4)C31—C32—C33—C282.0 (6)
C7—O1—C15—C16177.1 (3)C26—O4—C34—C35176.2 (3)
C17—N3—C16—C15123.2 (3)C36—N6—C35—C34123.1 (3)
C19—N3—C16—C1569.1 (4)C38—N6—C35—C3469.5 (4)
O1—C15—C16—N360.9 (4)O4—C34—C35—N660.0 (4)
C16—N3—C17—O21.2 (5)C35—N6—C36—O50.0 (5)
C19—N3—C17—O2170.2 (3)C38—N6—C36—O5168.8 (3)
C16—N3—C17—O3178.6 (3)C35—N6—C36—O6178.5 (3)
C19—N3—C17—O39.6 (4)C38—N6—C36—O69.7 (4)
C18—O3—C17—O2176.8 (4)C37—O6—C36—O5177.0 (3)
C18—O3—C17—N33.4 (4)C37—O6—C36—N64.4 (4)
C17—O3—C18—C1914.1 (4)C36—O6—C37—C3815.8 (4)
C17—N3—C19—C1817.4 (4)C36—N6—C38—C3718.4 (4)
C16—N3—C19—C18173.9 (3)C35—N6—C38—C37173.1 (3)
O3—C18—C19—N318.0 (4)O6—C37—C38—N619.7 (4)

Experimental details

Crystal data
Chemical formulaC19H17N3O3
Mr335.36
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)173
a, b, c (Å)10.1392 (4), 9.1398 (4), 34.8462 (15)
V3)3229.2 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.35 × 0.30
Data collection
DiffractometerBruker X8 APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25550, 4767, 4101
Rint0.029
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.123, 1.03
No. of reflections4767
No. of parameters451
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.21
Absolute structure4149 Friedel pairs merged

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

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

References

First citationAhoya, C. A., Bouhfid, R., Daouda, B., Essassi, E. M. & El Ammari, L. (2010). Acta Cryst. E66, o1050.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). 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. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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Volume 67| Part 5| May 2011| Page o1235
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