N-(4-Meth-oxy-phen-yl)-N'-(5-nitro-1,3-thia-zol-2-yl)urea.

The title compound, C(11)H(10)N(4)O(4)S, is a derivative of N-(4-meth-oxy-benz-yl)-N'-(5-nitro-1,3-thia-zol-2-yl)urea (AR-A014418), a known glycogen synthase kinase 3β (GSK-3β) inhibitor. All non-H atoms in the mol-ecule are essentially coplanar, with an r.m.s. deviation of 0.045 Å and a maximum deviation of 0.115 (2) Å for the carbonyl O atom. In the crystal structure, mol-ecules are linked via N-H⋯O hydrogen bonds into one-dimensional chains along [101].

Related literature

For background information on the preparation and activity of AR-A014418, see: Bhat et al. (2003 ▶); Inestrosa et al. (2006 ▶). For the radiolabelling procedure of AR-A014418 with carbon-11, see: Vasdev et al. (2005 ▶). For the crystal structure of AR-A014418, see: Vasdev et al. (2007 ▶).

Experimental

Crystal data

C11H10N4O4S

M = 294.29

Monoclinic,

a = 6.8740 (3) Å

b = 12.5840 (7) Å

c = 14.6861 (5) Å

β = 101.622 (3)°

V = 1244.34 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 150 K

0.28 × 0.24 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.718, T max = 0.948

8106 measured reflections

2825 independent reflections

1979 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.07

2825 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.51 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032186/su2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032186/su2205Isup2.hkl

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

C11H10N4O4S	F(000) = 608
Mr = 294.29	Dx = 1.571 Mg m−3
Monoclinic, P21/n	Melting point: 454 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.8740 (3) Å	Cell parameters from 3592 reflections
b = 12.5840 (7) Å	θ = 2.6–27.5°
c = 14.6861 (5) Å	µ = 0.28 mm−1
β = 101.622 (3)°	T = 150 K
V = 1244.34 (10) Å3	Block, red
Z = 4	0.28 × 0.24 × 0.22 mm

Nonius KappaCCD diffractometer	2825 independent reflections
Radiation source: fine-focus sealed tube	1979 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.8°
φ scans and ω scans with κ offsets	h = −8→8
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→16
Tmin = 0.718, Tmax = 0.948	l = −17→19
8106 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.3053P] where P = (Fo2 + 2Fc2)/3
2825 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expr ession of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.12900 (8)	0.68571 (5)	0.41433 (3)	0.0246 (2)
O1	0.2254 (2)	0.48461 (14)	0.47569 (10)	0.0306 (4)
O2	0.5006 (3)	0.00530 (13)	0.62455 (11)	0.0340 (4)
O3	−0.0126 (3)	0.97318 (14)	0.33409 (11)	0.0347 (4)
O4	0.0063 (3)	0.82488 (15)	0.25900 (11)	0.0367 (5)
N1	0.2026 (3)	0.79137 (16)	0.57084 (12)	0.0277 (5)
N2	0.2668 (3)	0.61085 (16)	0.58904 (13)	0.0268 (5)
H2N	0.327 (4)	0.627 (2)	0.6449 (19)	0.042 (8)*
N3	0.3514 (3)	0.44014 (16)	0.62860 (13)	0.0253 (5)
H3N	0.380 (4)	0.466 (2)	0.6845 (19)	0.037 (8)*
N4	0.0257 (3)	0.87648 (16)	0.33258 (13)	0.0270 (5)
C1	0.0930 (3)	0.82155 (19)	0.41566 (14)	0.0232 (5)
C2	0.1399 (3)	0.8632 (2)	0.50308 (15)	0.0267 (5)
H2A	0.1292	0.9369	0.5153	0.032*
C3	0.2033 (3)	0.69504 (18)	0.53334 (15)	0.0224 (5)
C4	0.2790 (3)	0.50759 (19)	0.55815 (15)	0.0243 (5)
C5	0.3832 (3)	0.32879 (18)	0.62462 (15)	0.0223 (5)
C6	0.3583 (3)	0.2717 (2)	0.54193 (15)	0.0245 (5)
H6A	0.3153	0.3064	0.4839	0.029*
C7	0.3970 (3)	0.1640 (2)	0.54544 (15)	0.0258 (5)
H7A	0.3791	0.1245	0.4892	0.031*
C8	0.4620 (3)	0.11186 (19)	0.63008 (15)	0.0253 (5)
C9	0.4842 (4)	0.1688 (2)	0.71214 (16)	0.0281 (6)
H9A	0.5265	0.1342	0.7702	0.034*
C10	0.4439 (4)	0.2773 (2)	0.70889 (16)	0.0277 (5)
H10A	0.4583	0.3164	0.7651	0.033*
C11	0.5519 (4)	−0.0525 (2)	0.70992 (17)	0.0360 (6)
H11A	0.5715	−0.1276	0.6965	0.054*
H11B	0.4446	−0.0460	0.7445	0.054*
H11C	0.6749	−0.0236	0.7472	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0269 (3)	0.0260 (4)	0.0198 (3)	0.0001 (2)	0.0024 (2)	−0.0017 (2)
O1	0.0405 (10)	0.0273 (10)	0.0225 (9)	0.0016 (8)	0.0028 (7)	−0.0024 (7)
O2	0.0482 (11)	0.0242 (9)	0.0304 (9)	0.0047 (8)	0.0097 (8)	0.0018 (7)
O3	0.0418 (11)	0.0279 (10)	0.0335 (10)	0.0046 (8)	0.0057 (8)	0.0080 (8)
O4	0.0450 (11)	0.0437 (12)	0.0193 (8)	0.0073 (9)	0.0015 (7)	−0.0019 (8)
N1	0.0368 (12)	0.0251 (11)	0.0214 (10)	0.0020 (9)	0.0059 (8)	−0.0009 (8)
N2	0.0352 (12)	0.0240 (11)	0.0205 (10)	0.0011 (9)	0.0040 (8)	−0.0033 (9)
N3	0.0315 (11)	0.0238 (11)	0.0204 (10)	0.0003 (9)	0.0048 (8)	−0.0014 (9)
N4	0.0239 (11)	0.0318 (12)	0.0250 (10)	0.0008 (9)	0.0041 (8)	0.0044 (9)
C1	0.0226 (12)	0.0249 (13)	0.0223 (11)	0.0005 (10)	0.0049 (9)	0.0036 (10)
C2	0.0310 (13)	0.0242 (13)	0.0246 (12)	0.0003 (10)	0.0046 (9)	−0.0005 (10)
C3	0.0241 (12)	0.0231 (13)	0.0206 (11)	−0.0022 (9)	0.0063 (8)	−0.0015 (9)
C4	0.0243 (12)	0.0251 (13)	0.0247 (12)	−0.0007 (10)	0.0079 (9)	−0.0009 (10)
C5	0.0206 (11)	0.0247 (13)	0.0226 (11)	−0.0003 (9)	0.0070 (8)	0.0002 (10)
C6	0.0233 (12)	0.0285 (14)	0.0219 (11)	0.0006 (10)	0.0051 (9)	0.0007 (10)
C7	0.0253 (12)	0.0293 (14)	0.0233 (11)	−0.0025 (10)	0.0063 (9)	−0.0030 (10)
C8	0.0257 (12)	0.0214 (12)	0.0309 (12)	0.0006 (10)	0.0105 (9)	0.0002 (10)
C9	0.0310 (13)	0.0314 (14)	0.0231 (11)	0.0006 (11)	0.0087 (9)	0.0044 (10)
C10	0.0338 (14)	0.0273 (13)	0.0235 (12)	0.0006 (11)	0.0097 (10)	−0.0020 (10)
C11	0.0477 (16)	0.0261 (14)	0.0345 (14)	0.0045 (12)	0.0089 (11)	0.0074 (11)

S1—C3	1.723 (2)	C1—C2	1.364 (3)
S1—C1	1.728 (2)	C2—H2A	0.9500
O1—C4	1.227 (3)	C5—C10	1.385 (3)
O2—C8	1.373 (3)	C5—C6	1.391 (3)
O2—C11	1.431 (3)	C6—C7	1.381 (3)
O3—N4	1.246 (3)	C6—H6A	0.9500
O4—N4	1.245 (2)	C7—C8	1.397 (3)
N1—C3	1.332 (3)	C7—H7A	0.9500
N1—C2	1.349 (3)	C8—C9	1.384 (3)
N2—C3	1.356 (3)	C9—C10	1.391 (3)
N2—C4	1.384 (3)	C9—H9A	0.9500
N2—H2N	0.86 (3)	C10—H10A	0.9500
N3—C4	1.353 (3)	C11—H11A	0.9800
N3—C5	1.421 (3)	C11—H11B	0.9800
N3—H3N	0.87 (3)	C11—H11C	0.9800
N4—C1	1.398 (3)
C3—S1—C1	86.27 (11)	C10—C5—C6	120.0 (2)
C8—O2—C11	117.49 (19)	C10—C5—N3	116.5 (2)
C3—N1—C2	109.40 (18)	C6—C5—N3	123.5 (2)
C3—N2—C4	124.68 (19)	C7—C6—C5	119.0 (2)
C3—N2—H2N	115.2 (19)	C7—C6—H6A	120.5
C4—N2—H2N	118.6 (19)	C5—C6—H6A	120.5
C4—N3—C5	128.5 (2)	C6—C7—C8	121.3 (2)
C4—N3—H3N	117.8 (18)	C6—C7—H7A	119.4
C5—N3—H3N	113.6 (18)	C8—C7—H7A	119.4
O4—N4—O3	122.61 (19)	O2—C8—C9	124.7 (2)
O4—N4—C1	117.3 (2)	O2—C8—C7	115.9 (2)
O3—N4—C1	120.09 (19)	C9—C8—C7	119.4 (2)
C2—C1—N4	127.3 (2)	C8—C9—C10	119.5 (2)
C2—C1—S1	112.58 (17)	C8—C9—H9A	120.3
N4—C1—S1	120.16 (17)	C10—C9—H9A	120.3
N1—C2—C1	114.6 (2)	C5—C10—C9	120.8 (2)
N1—C2—H2A	122.7	C5—C10—H10A	119.6
C1—C2—H2A	122.7	C9—C10—H10A	119.6
N1—C3—N2	119.29 (19)	O2—C11—H11A	109.5
N1—C3—S1	117.15 (17)	O2—C11—H11B	109.5
N2—C3—S1	123.53 (17)	H11A—C11—H11B	109.5
O1—C4—N3	126.7 (2)	O2—C11—H11C	109.5
O1—C4—N2	121.2 (2)	H11A—C11—H11C	109.5
N3—C4—N2	112.05 (19)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4i	0.86 (3)	1.97 (3)	2.817 (3)	168 (3)
N3—H3N···O3i	0.87 (3)	2.30 (3)	3.168 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O4i	0.86 (3)	1.97 (3)	2.817 (3)	168 (3)
N3—H3N⋯O3i	0.87 (3)	2.30 (3)	3.168 (2)	174 (2)

Symmetry code: (i) .