3-{2-[(3-{(E)-2-[4-(Dimethyl-amino)-phen-yl]ethen-yl}quinoxalin-2-yl)-oxy]eth-yl}-1,3-oxazolidin-2-one monohydrate.

In the title compound, C(23)H(24)N(4)O(3)·H(2)O, 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 mol-ecule 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 = 422.48

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.137

S = 1.03

5836 reflections

290 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.25 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054481/xu5414sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811054481/xu5414Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H24N4O3·H2O	F(000) = 896
Mr = 422.48	Dx = 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

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

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(Fo2) + (0.0694P)2 + 0.5463P] where P = (Fo2 + 2Fc2)/3
5836 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.48 e Å−3
2 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .