3-{2-[(3-{(E)-2-[4-(Dimethyl­amino)­phen­yl]ethen­yl}quinoxalin-2-yl)­oxy]eth­yl}-1,3-oxazolidin-2-one monohydrate

Ramli, Y.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811054481

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o241

doi:10.1107/S1600536811054481

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3-{2-[(3-{(E)-2-[4-(Dimethylamino)phenyl]ethenyl}quinoxalin-2-yl)oxy]ethyl}-1,3-oxazolidin-2-one monohydrate

Youssef Ramli,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 December 2011; accepted 18 December 2011; online 23 December 2011)

In the title compound, C₂₃H₂₄N₄O₃·H₂O, the 1,3-oxazoline ring is nearly planar [maximum deviation = 0.059 (2) Å] and its mean plane is twisted by 30.12 (8)° with respect to the quinoxaline fused-ring system; the benzene ring is nearly coplanar with the quinoxaline fused-ring system [dihedral angle = 2.52 (2)°]. The water molecule of crystallization is hydrogen-bond donor to an N atom of the quinoxaline ring system as well as an O atom of the oxazolinone unit, the two hydrogen bonds generating a chain running along the c axis.

Related literature

For general background, see: Noolvi et al. (2011 ).

Experimental

Crystal data

C₂₃H₂₄N₄O₃·H₂O
M_r = 422.48
Monoclinic, P 2₁ /c
a = 7.20980 (1) Å
b = 23.3271 (4) Å
c = 12.3994 (2) Å
β = 98.119 (1)°
V = 2064.47 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.21 × 0.20 × 0.15 mm

Data collection

Bruker APEX DUO diffractometer
28134 measured reflections
5836 independent reflections
4141 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.03
5836 reflections
290 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯N1	0.87 (1)	2.18 (1)	3.039 (2)	170 (2)
O1w—H12⋯O3ⁱ	0.86 (1)	1.96 (1)	2.820 (2)	176 (3)
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054481/xu5414sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054481/xu5414Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054481/xu5414Isup3.cml

checkCIF report

Comment top

2-Chloro-3-(4-dimethylaminostyryl)quinoxaline is a reactant for the synthesis of quinoxaline derivatives that possess anti-cancer properties (Noolvi et al., 2011); the chloro substitutent is exchanged for other organic radicals. We have used the 3-(4-dimethylaminostyryl)quinoxaline as reactant to furnish the title derivative (Scheme I). The quinoxaline fused-ring and the phenylene ring are nearly co-planar (dihedral angle 2.52 (2)°) (Fig. 1). The water molecule is hydrogen bond donor to an N atom of the fused-ring as well as an O atom of the oxazolinone unit, the two hydrogen bonds generating a linear chain running along the c-axis of the monoclinic unit cell (Table 1).

Related literature top

For general background, see: Noolvi et al. (2011).

Experimental top

To 3-(4-dimethylaminostyryl)quinoxaline (1 g, 3.43 mmol), potassium carbonate (0.71 g, 5.15 mmol) and a catalytic amount of tetra-n-butylammonium bromide in DMF (40 ml) was added bis(2-chloroethyl)amine hydrochloride (1.22 g, 6.87 mmol). The mixture was heated for 48 hours. After the completion of the reaction (as monitored by TLC), the inorganic material salt was filtered and the solvent was removed under reduced pressure. The solid product was purified by recrystallization from ethanol to afford colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 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

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₃H₂₄N₄O₃^.H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-{2-[(3-{(E)-2-[4-(Dimethylamino)phenyl]ethenyl}quinoxalin-2- yl)oxy]ethyl}-1,3-oxazolidin-2-one monohydrate top

Crystal data top

C₂₃H₂₄N₄O₃·H₂O	F(000) = 896
M_r = 422.48	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7579 reflections
a = 7.20980 (1) Å	θ = 3.0–30.1°
b = 23.3271 (4) Å	µ = 0.10 mm⁻¹
c = 12.3994 (2) Å	T = 293 K
β = 98.119 (1)°	Prism, colorless
V = 2064.47 (6) Å³	0.21 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker APEX DUO diffractometer	4141 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 30.1°, θ_min = 2.4°
ω scans	h = −10→10
28134 measured reflections	k = −32→27
5836 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0694P)² + 0.5463P] where P = (F_o² + 2F_c²)/3
5836 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.48 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₃H₂₄N₄O₃·H₂O	V = 2064.47 (6) Å³
M_r = 422.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.20980 (1) Å	µ = 0.10 mm⁻¹
b = 23.3271 (4) Å	T = 293 K
c = 12.3994 (2) Å	0.21 × 0.20 × 0.15 mm
β = 98.119 (1)°

Data collection top

Bruker APEX DUO diffractometer	4141 reflections with I > 2σ(I)
28134 measured reflections	R_int = 0.031
5836 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.48 e Å⁻³
5836 reflections	Δρ_min = −0.25 e Å⁻³
290 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.69604 (14)	0.57099 (4)	0.70080 (7)	0.0248 (2)
O2	0.68168 (18)	0.42279 (4)	0.99270 (9)	0.0414 (3)
O3	0.74191 (19)	0.50321 (5)	1.08888 (9)	0.0436 (3)
O1W	0.8486 (2)	0.59976 (6)	0.21995 (13)	0.0614 (4)
H11	0.797 (3)	0.5986 (11)	0.2789 (14)	0.080 (8)*
H12	0.813 (4)	0.5698 (8)	0.1822 (19)	0.088 (9)*
N1	0.65125 (15)	0.61020 (4)	0.42003 (9)	0.0201 (2)
N2	0.60511 (15)	0.65809 (4)	0.62458 (8)	0.0200 (2)
N3	0.73026 (18)	0.50212 (5)	0.90253 (9)	0.0271 (3)
N4	0.95701 (19)	0.25635 (5)	0.38066 (10)	0.0296 (3)
C1	0.59653 (17)	0.66630 (5)	0.42868 (10)	0.0179 (2)
C2	0.56427 (19)	0.70093 (5)	0.33486 (10)	0.0226 (3)
H2	0.5819	0.6858	0.2677	0.027*
C3	0.5071 (2)	0.75683 (5)	0.34146 (10)	0.0238 (3)
H3	0.4860	0.7793	0.2790	0.029*
C4	0.48053 (19)	0.78010 (5)	0.44295 (11)	0.0229 (3)
H4	0.4410	0.8179	0.4471	0.027*
C5	0.51243 (19)	0.74744 (5)	0.53594 (10)	0.0217 (3)
H5	0.4945	0.7632	0.6026	0.026*
C6	0.57205 (17)	0.69021 (5)	0.53078 (10)	0.0178 (2)
C7	0.68059 (18)	0.57926 (5)	0.50954 (10)	0.0189 (2)
C8	0.65714 (18)	0.60568 (5)	0.61326 (10)	0.0194 (3)
C9	0.6853 (2)	0.59576 (5)	0.80636 (10)	0.0265 (3)
H9A	0.5564	0.5963	0.8205	0.032*
H9B	0.7320	0.6348	0.8091	0.032*
C10	0.8030 (2)	0.55941 (6)	0.88980 (11)	0.0287 (3)
H10A	0.9277	0.5562	0.8695	0.034*
H10B	0.8145	0.5788	0.9596	0.034*
C11	0.7117 (3)	0.45883 (6)	0.81770 (12)	0.0360 (4)
H11A	0.8293	0.4526	0.7899	0.043*
H11B	0.6155	0.4690	0.7579	0.043*
C12	0.6556 (3)	0.40662 (7)	0.87927 (14)	0.0447 (4)
H12A	0.5258	0.3966	0.8551	0.054*
H12B	0.7339	0.3740	0.8676	0.054*
C13	0.7202 (2)	0.47953 (6)	1.00090 (11)	0.0285 (3)
C14	0.73685 (19)	0.51947 (5)	0.50739 (11)	0.0223 (3)
H14	0.7641	0.5005	0.5737	0.027*
C15	0.75223 (18)	0.48975 (5)	0.41639 (10)	0.0209 (3)
H15	0.7254	0.5094	0.3507	0.025*
C16	0.80663 (17)	0.43002 (5)	0.41021 (10)	0.0192 (2)
C17	0.82357 (18)	0.40565 (5)	0.30881 (10)	0.0215 (3)
H17	0.7998	0.4283	0.2466	0.026*
C18	0.87439 (19)	0.34909 (5)	0.29830 (10)	0.0232 (3)
H18	0.8852	0.3345	0.2296	0.028*
C19	0.91014 (18)	0.31313 (5)	0.39002 (10)	0.0210 (3)
C20	0.89460 (19)	0.33767 (5)	0.49262 (10)	0.0232 (3)
H20	0.9185	0.3152	0.5550	0.028*
C21	0.84471 (19)	0.39423 (5)	0.50171 (10)	0.0230 (3)
H21	0.8360	0.4092	0.5704	0.028*
C22	0.9988 (2)	0.23508 (6)	0.27733 (13)	0.0367 (4)
H22A	0.8892	0.2382	0.2238	0.055*
H22B	1.0363	0.1956	0.2849	0.055*
H22C	1.0985	0.2573	0.2546	0.055*
C23	1.0080 (2)	0.22143 (6)	0.47718 (13)	0.0299 (3)
H23A	0.9014	0.2173	0.5150	0.045*
H23B	1.1081	0.2396	0.5241	0.045*
H23C	1.0480	0.1843	0.4562	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0397 (6)	0.0184 (4)	0.0163 (4)	0.0043 (4)	0.0042 (4)	0.0032 (3)
O2	0.0657 (8)	0.0242 (5)	0.0325 (6)	−0.0058 (5)	0.0006 (6)	0.0083 (4)
O3	0.0744 (9)	0.0343 (6)	0.0218 (5)	−0.0004 (6)	0.0059 (6)	0.0032 (4)
O1W	0.0989 (12)	0.0353 (7)	0.0591 (9)	−0.0211 (7)	0.0422 (9)	−0.0125 (6)
N1	0.0253 (6)	0.0156 (5)	0.0198 (5)	0.0005 (4)	0.0044 (4)	−0.0002 (4)
N2	0.0262 (6)	0.0169 (5)	0.0173 (5)	0.0008 (4)	0.0041 (4)	0.0008 (4)
N3	0.0408 (7)	0.0209 (5)	0.0192 (5)	−0.0012 (5)	0.0027 (5)	0.0024 (4)
N4	0.0439 (7)	0.0178 (5)	0.0278 (6)	0.0079 (5)	0.0076 (6)	−0.0010 (4)
C1	0.0207 (6)	0.0158 (5)	0.0172 (5)	−0.0004 (4)	0.0026 (5)	−0.0005 (4)
C2	0.0317 (7)	0.0200 (6)	0.0162 (6)	0.0013 (5)	0.0037 (5)	0.0000 (4)
C3	0.0321 (7)	0.0201 (6)	0.0188 (6)	0.0023 (5)	0.0026 (5)	0.0042 (4)
C4	0.0294 (7)	0.0159 (5)	0.0238 (6)	0.0031 (5)	0.0051 (5)	0.0008 (4)
C5	0.0282 (7)	0.0186 (5)	0.0189 (6)	0.0027 (5)	0.0058 (5)	−0.0015 (4)
C6	0.0197 (6)	0.0167 (5)	0.0170 (6)	−0.0001 (4)	0.0026 (5)	0.0013 (4)
C7	0.0214 (6)	0.0158 (5)	0.0195 (6)	−0.0007 (4)	0.0035 (5)	−0.0005 (4)
C8	0.0229 (6)	0.0181 (5)	0.0175 (6)	−0.0003 (4)	0.0034 (5)	0.0020 (4)
C9	0.0417 (8)	0.0205 (6)	0.0173 (6)	0.0018 (5)	0.0044 (6)	0.0012 (4)
C10	0.0359 (8)	0.0261 (7)	0.0229 (7)	−0.0056 (6)	−0.0006 (6)	0.0047 (5)
C11	0.0535 (10)	0.0285 (7)	0.0251 (7)	−0.0012 (7)	0.0024 (7)	−0.0029 (5)
C12	0.0713 (13)	0.0238 (7)	0.0367 (9)	0.0001 (7)	−0.0008 (9)	−0.0008 (6)
C13	0.0366 (8)	0.0239 (6)	0.0248 (7)	0.0036 (6)	0.0038 (6)	0.0067 (5)
C14	0.0281 (7)	0.0154 (5)	0.0235 (6)	0.0019 (5)	0.0044 (5)	0.0018 (4)
C15	0.0231 (6)	0.0168 (5)	0.0229 (6)	0.0000 (5)	0.0031 (5)	0.0017 (4)
C16	0.0212 (6)	0.0156 (5)	0.0209 (6)	−0.0009 (4)	0.0034 (5)	−0.0006 (4)
C17	0.0262 (7)	0.0203 (6)	0.0181 (6)	0.0003 (5)	0.0038 (5)	0.0018 (4)
C18	0.0280 (7)	0.0225 (6)	0.0196 (6)	0.0017 (5)	0.0050 (5)	−0.0022 (4)
C19	0.0230 (6)	0.0166 (5)	0.0236 (6)	0.0003 (5)	0.0040 (5)	−0.0019 (4)
C20	0.0317 (7)	0.0186 (6)	0.0193 (6)	0.0010 (5)	0.0036 (5)	0.0020 (4)
C21	0.0314 (7)	0.0194 (6)	0.0185 (6)	−0.0001 (5)	0.0048 (5)	−0.0019 (4)
C22	0.0492 (10)	0.0269 (7)	0.0354 (8)	0.0130 (6)	0.0114 (7)	−0.0064 (6)
C23	0.0334 (8)	0.0194 (6)	0.0368 (8)	0.0039 (5)	0.0048 (6)	0.0037 (5)

Geometric parameters (Å, º) top

O1—C8	1.3512 (14)	C9—H9A	0.9700
O1—C9	1.4428 (15)	C9—H9B	0.9700
O2—C13	1.3532 (17)	C10—H10A	0.9700
O2—C12	1.443 (2)	C10—H10B	0.9700
O3—C13	1.2130 (17)	C11—C12	1.522 (2)
O1W—H11	0.867 (10)	C11—H11A	0.9700
O1W—H12	0.861 (10)	C11—H11B	0.9700
N1—C7	1.3158 (15)	C12—H12A	0.9700
N1—C1	1.3754 (15)	C12—H12B	0.9700
N2—C8	1.2922 (15)	C14—C15	1.3422 (17)
N2—C6	1.3757 (15)	C14—H14	0.9300
N3—C13	1.3401 (16)	C15—C16	1.4523 (16)
N3—C11	1.4507 (18)	C15—H15	0.9300
N3—C10	1.4522 (17)	C16—C17	1.4008 (16)
N4—C19	1.3760 (16)	C16—C21	1.4042 (17)
N4—C22	1.4447 (17)	C17—C18	1.3803 (17)
N4—C23	1.4514 (18)	C17—H17	0.9300
C1—C2	1.4083 (16)	C18—C19	1.4074 (17)
C1—C6	1.4170 (15)	C18—H18	0.9300
C2—C3	1.3734 (17)	C19—C20	1.4138 (16)
C2—H2	0.9300	C20—C21	1.3762 (17)
C3—C4	1.4082 (17)	C20—H20	0.9300
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.3739 (17)	C22—H22A	0.9600
C4—H4	0.9300	C22—H22B	0.9600
C5—C6	1.4068 (16)	C22—H22C	0.9600
C5—H5	0.9300	C23—H23A	0.9600
C7—C14	1.4536 (16)	C23—H23B	0.9600
C7—C8	1.4575 (16)	C23—H23C	0.9600
C9—C10	1.504 (2)

C8—O1—C9	117.20 (9)	C12—C11—H11A	111.5
C13—O2—C12	109.03 (11)	N3—C11—H11B	111.5
H11—O1W—H12	108 (2)	C12—C11—H11B	111.5
C7—N1—C1	118.03 (10)	H11A—C11—H11B	109.3
C8—N2—C6	116.22 (10)	O2—C12—C11	105.82 (12)
C13—N3—C11	112.01 (11)	O2—C12—H12A	110.6
C13—N3—C10	121.85 (12)	C11—C12—H12A	110.6
C11—N3—C10	124.02 (11)	O2—C12—H12B	110.6
C19—N4—C22	119.33 (11)	C11—C12—H12B	110.6
C19—N4—C23	120.48 (11)	H12A—C12—H12B	108.7
C22—N4—C23	118.58 (11)	O3—C13—N3	128.51 (13)
N1—C1—C2	119.81 (10)	O3—C13—O2	120.80 (12)
N1—C1—C6	121.16 (10)	N3—C13—O2	110.69 (12)
C2—C1—C6	119.03 (10)	C15—C14—C7	124.57 (12)
C3—C2—C1	120.75 (11)	C15—C14—H14	117.7
C3—C2—H2	119.6	C7—C14—H14	117.7
C1—C2—H2	119.6	C14—C15—C16	126.51 (12)
C2—C3—C4	119.93 (11)	C14—C15—H15	116.7
C2—C3—H3	120.0	C16—C15—H15	116.7
C4—C3—H3	120.0	C17—C16—C21	116.87 (11)
C5—C4—C3	120.56 (11)	C17—C16—C15	119.68 (11)
C5—C4—H4	119.7	C21—C16—C15	123.45 (11)
C3—C4—H4	119.7	C18—C17—C16	122.05 (11)
C4—C5—C6	120.27 (11)	C18—C17—H17	119.0
C4—C5—H5	119.9	C16—C17—H17	119.0
C6—C5—H5	119.9	C17—C18—C19	120.94 (11)
N2—C6—C5	119.74 (10)	C17—C18—H18	119.5
N2—C6—C1	120.82 (10)	C19—C18—H18	119.5
C5—C6—C1	119.44 (11)	N4—C19—C18	121.65 (11)
N1—C7—C14	121.53 (11)	N4—C19—C20	121.16 (11)
N1—C7—C8	119.17 (10)	C18—C19—C20	117.19 (11)
C14—C7—C8	119.30 (11)	C21—C20—C19	121.11 (11)
N2—C8—O1	120.66 (10)	C21—C20—H20	119.4
N2—C8—C7	124.58 (11)	C19—C20—H20	119.4
O1—C8—C7	114.76 (10)	C20—C21—C16	121.83 (11)
O1—C9—C10	107.50 (11)	C20—C21—H21	119.1
O1—C9—H9A	110.2	C16—C21—H21	119.1
C10—C9—H9A	110.2	N4—C22—H22A	109.5
O1—C9—H9B	110.2	N4—C22—H22B	109.5
C10—C9—H9B	110.2	H22A—C22—H22B	109.5
H9A—C9—H9B	108.5	N4—C22—H22C	109.5
N3—C10—C9	114.60 (12)	H22A—C22—H22C	109.5
N3—C10—H10A	108.6	H22B—C22—H22C	109.5
C9—C10—H10A	108.6	N4—C23—H23A	109.5
N3—C10—H10B	108.6	N4—C23—H23B	109.5
C9—C10—H10B	108.6	H23A—C23—H23B	109.5
H10A—C10—H10B	107.6	N4—C23—H23C	109.5
N3—C11—C12	101.37 (12)	H23A—C23—H23C	109.5
N3—C11—H11A	111.5	H23B—C23—H23C	109.5

C7—N1—C1—C2	179.80 (12)	C13—N3—C11—C12	9.09 (18)
C7—N1—C1—C6	−0.09 (18)	C10—N3—C11—C12	172.75 (14)
N1—C1—C2—C3	179.12 (12)	C13—O2—C12—C11	8.34 (19)
C6—C1—C2—C3	−0.99 (19)	N3—C11—C12—O2	−10.11 (18)
C1—C2—C3—C4	0.1 (2)	C11—N3—C13—O3	175.00 (16)
C2—C3—C4—C5	0.4 (2)	C10—N3—C13—O3	10.9 (3)
C3—C4—C5—C6	−0.1 (2)	C11—N3—C13—O2	−4.46 (18)
C8—N2—C6—C5	179.13 (12)	C10—N3—C13—O2	−168.53 (13)
C8—N2—C6—C1	−0.61 (18)	C12—O2—C13—O3	177.73 (16)
C4—C5—C6—N2	179.43 (12)	C12—O2—C13—N3	−2.76 (19)
C4—C5—C6—C1	−0.83 (19)	N1—C7—C14—C15	−4.4 (2)
N1—C1—C6—N2	0.96 (18)	C8—C7—C14—C15	175.96 (13)
C2—C1—C6—N2	−178.93 (11)	C7—C14—C15—C16	−179.58 (12)
N1—C1—C6—C5	−178.77 (12)	C14—C15—C16—C17	−177.43 (13)
C2—C1—C6—C5	1.34 (18)	C14—C15—C16—C21	2.4 (2)
C1—N1—C7—C14	179.37 (11)	C21—C16—C17—C18	0.28 (19)
C1—N1—C7—C8	−0.99 (18)	C15—C16—C17—C18	−179.85 (12)
C6—N2—C8—O1	178.87 (11)	C16—C17—C18—C19	0.5 (2)
C6—N2—C8—C7	−0.53 (19)	C22—N4—C19—C18	9.7 (2)
C9—O1—C8—N2	−2.79 (18)	C23—N4—C19—C18	174.98 (12)
C9—O1—C8—C7	176.67 (11)	C22—N4—C19—C20	−170.81 (14)
N1—C7—C8—N2	1.4 (2)	C23—N4—C19—C20	−5.5 (2)
C14—C7—C8—N2	−178.95 (12)	C17—C18—C19—N4	178.58 (13)
N1—C7—C8—O1	−178.04 (11)	C17—C18—C19—C20	−0.97 (19)
C14—C7—C8—O1	1.61 (17)	N4—C19—C20—C21	−178.92 (13)
C8—O1—C9—C10	−157.88 (11)	C18—C19—C20—C21	0.64 (19)
C13—N3—C10—C9	−133.37 (14)	C19—C20—C21—C16	0.2 (2)
C11—N3—C10—C9	64.51 (19)	C17—C16—C21—C20	−0.62 (19)
O1—C9—C10—N3	−67.73 (15)	C15—C16—C21—C20	179.52 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N1	0.87 (1)	2.18 (1)	3.039 (2)	170 (2)
O1w—H12···O3ⁱ	0.86 (1)	1.96 (1)	2.820 (2)	176 (3)

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄N₄O₃·H₂O
M_r	422.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.20980 (1), 23.3271 (4), 12.3994 (2)
β (°)	98.119 (1)
V (Å³)	2064.47 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEX DUO diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	28134, 5836, 4141
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.03
No. of reflections	5836
No. of parameters	290
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.25

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N1	0.87 (1)	2.18 (1)	3.039 (2)	170 (2)
O1w—H12···O3ⁱ	0.86 (1)	1.96 (1)	2.820 (2)	176 (3)

Symmetry code: (i) x, y, z−1.

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Noolvi, M., Patel, H. M., Bhardwaj, V. & Chauhan, A. (2011). Eur. J. Med. Chem. 46, 2327–2346. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Page o241

doi:10.1107/S1600536811054481

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

3-{2-[(3-{(E)-2-[4-(Di­methyl­amino)­phen­yl]ethen­yl}quinoxalin-2-yl)­­oxy]eth­yl}-1,3-oxazolidin-2-one monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{2-[(3-{(E)-2-[4-(Dimethylamino)phenyl]ethenyl}quinoxalin-2-yl)oxy]ethyl}-1,3-oxazolidin-2-one monohydrate