6-(2-Chloro-benz-yl)-1-(4-chloro-phen-yl)-7-hy-droxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one.

The title compound, C(19)H(15)Cl(2)N(3)O(2), was obtained by a one-step cyclo-condensation of 2-amino-1-(4-chloro-phen-yl)imidazoline with diethyl (2-chloro-benz-yl)malonate under basic conditions. In the crystalline state, the mol-ecule exists as the 7-hy-droxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chloro-phenyl and chloro-benzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the mol-ecule is influenced by the intra-molecular C-H⋯O and C-H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis. These chains are further stabilized by weak C-H⋯Cl and π-π inter-actions [centroid-centroid distance = 3.6707 (12) Å].

Related literature

For background to dioxo derivatives of fused imidazoline ring systems, their biological activity and medical applications, see: Matosiuk, Fidecka, Antkiewicz-Michaluk, Dybała et al. (2002) ▶; Matosiuk, Fidecka, Antkiewicz-Michaluk, Lipkowski et al. (2002 ▶). For the synthesis, see: Rządkowska et al. (2004 ▶). For a related structure, see: Wysocki et al. (2006 ▶). For structure inter­pretation tools, see: Allen et al. (1995 ▶); Allen (2002 ▶); Bruno et al. (2002 ▶). For resonance-assisted hydrogen bonds, see: Gilli et al. (1989 ▶).

Experimental

Crystal data

C19H15Cl2N3O2

M = 388.24

Monoclinic,

a = 11.4521 (3) Å

b = 12.8287 (4) Å

c = 11.7255 (3) Å

β = 96.283 (2)°

V = 1712.31 (8) Å3

Z = 4

Cu Kα radiation

μ = 3.58 mm−1

T = 296 K

0.26 × 0.25 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.415, T max = 0.674

12489 measured reflections

3040 independent reflections

2521 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.05

3040 reflections

280 parameters

All H-atom parameters refined

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003919X/fj2343sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003919X/fj2343Isup2.hkl

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

C19H15Cl2N3O2	F(000) = 800
Mr = 388.24	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3410 reflections
a = 11.4521 (3) Å	θ = 3.9–66.7°
b = 12.8287 (4) Å	µ = 3.58 mm−1
c = 11.7255 (3) Å	T = 296 K
β = 96.283 (2)°	Block, colourless
V = 1712.31 (8) Å3	0.26 × 0.25 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	3040 independent reflections
Radiation source: fine-focus sealed tube	2521 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 67.8°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→12
Tmin = 0.415, Tmax = 0.674	k = −15→8
12489 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.112	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.4965P] where P = (Fo2 + 2Fc2)/3
3040 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.29 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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=dPlane 1 m1 = -0.57842(0.00033) m2 = -0.67971(0.00033) m3 = -0.45102(0.00053) D = -11.68389(0.00244) Atom d s d/s (d/s)**2 N1 * -0.0460 0.0016 - 28.384 805.647 C2 * 0.0029 0.0018 1.594 2.541 N3 * 0.0198 0.0015 13.215 174.625 C4 * -0.0357 0.0023 - 15.771 248.720 C5 * 0.0819 0.0023 36.135 1305.707 N6 * 0.0038 0.0015 2.558 6.543 C7 * 0.0139 0.0017 7.983 63.731 C8 * 0.0007 0.0018 0.384 0.147 C9 * -0.0243 0.0018 - 13.656 186.495 ============ Sum((d/s)**2) for starred atoms 2794.157 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarityPlane 2 m1 = -0.71141(0.00065) m2 = -0.48107(0.00093) m3 = -0.51231(0.00073) D = -11.40891(0.00306) Atom d s d/s (d/s)**2 C21 * 0.0042 0.0018 2.264 5.124 C22 * -0.0048 0.0022 - 2.159 4.661 C23 * -0.0012 0.0023 - 0.496 0.246 C24 * 0.0051 0.0021 2.408 5.797 C25 * -0.0050 0.0024 - 2.037 4.149 C26 * -0.0018 0.0023 - 0.782 0.611 ============ Sum((d/s)**2) for starred atoms 20.589 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityPlane 3 m1 = -0.47124(0.00082) m2 = 0.42681(0.00103) m3 = -0.77186(0.00062) D = -3.90575(0.01406) Atom d s d/s (d/s)**2 C31 * -0.0026 0.0019 - 1.391 1.935 C32 * 0.0016 0.0021 0.757 0.573 C33 * 0.0031 0.0027 1.149 1.321 C34 * -0.0079 0.0031 - 2.556 6.533 C35 * 0.0042 0.0031 1.328 1.764 C36 * 0.0021 0.0024 0.859 0.738 ============ Sum((d/s)**2) for starred atoms 12.865 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityDihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 14.18 (0.06) 165.82 (0.06) 1 3 70.69 (0.06) 109.31 (0.06) 2 3 58.31 (0.06) 121.69 (0.06)

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 expression 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
N1	0.54690 (14)	0.58844 (13)	0.65922 (13)	0.0405 (4)
C2	0.45149 (16)	0.63750 (14)	0.69364 (15)	0.0345 (4)
N3	0.42905 (13)	0.59910 (12)	0.79699 (12)	0.0368 (4)
C4	0.5131 (2)	0.51928 (18)	0.84006 (18)	0.0470 (5)
H41	0.560 (2)	0.547 (2)	0.910 (2)	0.070*
H42	0.473 (2)	0.454 (2)	0.860 (2)	0.070*
C5	0.5851 (2)	0.50339 (18)	0.73916 (18)	0.0472 (5)
H51	0.670 (3)	0.511 (2)	0.762 (2)	0.071*
H52	0.567 (2)	0.430 (2)	0.703 (2)	0.071*
N6	0.39106 (13)	0.71171 (12)	0.63876 (12)	0.0362 (4)
C7	0.30136 (15)	0.75057 (14)	0.69309 (14)	0.0329 (4)
C8	0.27243 (16)	0.71925 (14)	0.79896 (15)	0.0349 (4)
C9	0.34131 (16)	0.63956 (14)	0.85735 (14)	0.0346 (4)
O10	0.24079 (12)	0.82712 (10)	0.63775 (11)	0.0402 (3)
H101	0.268 (2)	0.844 (2)	0.576 (2)	0.060*
O11	0.33241 (12)	0.60419 (10)	0.95466 (10)	0.0423 (3)
C12	0.17750 (17)	0.77055 (15)	0.85764 (17)	0.0390 (4)
H121	0.213 (2)	0.7977 (18)	0.933 (2)	0.059*
H122	0.150 (2)	0.832 (2)	0.814 (2)	0.059*
C21	0.59787 (16)	0.60289 (15)	0.55615 (15)	0.0384 (4)
C22	0.67539 (19)	0.52838 (18)	0.52397 (19)	0.0500 (5)
H221	0.691 (2)	0.465 (2)	0.568 (2)	0.075*
C23	0.7284 (2)	0.53957 (19)	0.4242 (2)	0.0534 (6)
H231	0.777 (3)	0.490 (2)	0.404 (2)	0.080*
C24	0.70459 (18)	0.62511 (18)	0.35695 (18)	0.0499 (5)
C25	0.6293 (2)	0.7008 (2)	0.3878 (2)	0.0568 (6)
H251	0.617 (3)	0.764 (2)	0.342 (2)	0.085*
C26	0.5754 (2)	0.69008 (19)	0.48719 (19)	0.0511 (5)
H261	0.529 (2)	0.742 (2)	0.507 (2)	0.077*
Cl27	0.77155 (6)	0.63967 (6)	0.23211 (5)	0.0784 (2)
C31	0.07284 (16)	0.70368 (15)	0.87807 (16)	0.0389 (4)
C32	−0.00662 (18)	0.73742 (19)	0.95069 (17)	0.0489 (5)
C33	−0.1022 (2)	0.6786 (3)	0.9736 (2)	0.0669 (7)
H331	−0.152 (3)	0.706 (3)	1.024 (3)	0.100*
C34	−0.1203 (2)	0.5828 (3)	0.9241 (3)	0.0747 (8)
H341	−0.183 (3)	0.540 (3)	0.942 (3)	0.112*
C35	−0.0442 (2)	0.5470 (2)	0.8503 (3)	0.0742 (8)
H351	−0.054 (3)	0.479 (3)	0.814 (3)	0.111*
C36	0.0516 (2)	0.60699 (18)	0.8281 (2)	0.0541 (5)
H361	0.103 (3)	0.581 (2)	0.779 (2)	0.081*
Cl37	0.01144 (6)	0.85933 (6)	1.01526 (7)	0.0825 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0425 (8)	0.0461 (9)	0.0342 (8)	0.0134 (7)	0.0110 (7)	0.0067 (7)
C2	0.0374 (9)	0.0386 (9)	0.0281 (8)	0.0033 (8)	0.0064 (7)	0.0001 (7)
N3	0.0419 (8)	0.0412 (8)	0.0283 (7)	0.0055 (7)	0.0082 (6)	0.0041 (6)
C4	0.0524 (12)	0.0506 (12)	0.0387 (10)	0.0142 (10)	0.0088 (9)	0.0098 (10)
C5	0.0523 (12)	0.0496 (12)	0.0405 (11)	0.0157 (10)	0.0089 (9)	0.0103 (9)
N6	0.0395 (8)	0.0411 (8)	0.0296 (7)	0.0070 (7)	0.0107 (6)	0.0026 (6)
C7	0.0364 (9)	0.0338 (9)	0.0293 (8)	0.0012 (7)	0.0071 (7)	0.0003 (7)
C8	0.0391 (9)	0.0364 (9)	0.0305 (9)	0.0004 (8)	0.0100 (7)	0.0008 (8)
C9	0.0397 (9)	0.0368 (9)	0.0284 (9)	−0.0036 (8)	0.0082 (7)	−0.0026 (7)
O10	0.0456 (7)	0.0434 (7)	0.0335 (7)	0.0109 (6)	0.0129 (6)	0.0068 (6)
O11	0.0570 (8)	0.0452 (7)	0.0265 (6)	0.0006 (6)	0.0127 (6)	0.0035 (6)
C12	0.0436 (10)	0.0387 (10)	0.0370 (10)	0.0016 (8)	0.0145 (8)	−0.0005 (9)
C21	0.0363 (9)	0.0467 (10)	0.0334 (9)	0.0055 (8)	0.0092 (7)	−0.0008 (8)
C22	0.0525 (12)	0.0496 (12)	0.0506 (12)	0.0134 (10)	0.0173 (10)	0.0013 (10)
C23	0.0525 (12)	0.0555 (13)	0.0557 (13)	0.0110 (11)	0.0212 (10)	−0.0078 (11)
C24	0.0458 (11)	0.0655 (14)	0.0408 (11)	0.0029 (10)	0.0162 (9)	−0.0037 (10)
C25	0.0606 (14)	0.0656 (14)	0.0476 (12)	0.0159 (12)	0.0211 (10)	0.0134 (11)
C26	0.0538 (12)	0.0584 (13)	0.0447 (11)	0.0178 (11)	0.0210 (9)	0.0086 (10)
Cl27	0.0858 (5)	0.1015 (5)	0.0555 (4)	0.0106 (4)	0.0425 (3)	0.0026 (3)
C31	0.0380 (9)	0.0458 (10)	0.0335 (9)	0.0007 (8)	0.0067 (7)	0.0036 (8)
C32	0.0413 (10)	0.0673 (14)	0.0395 (10)	0.0036 (10)	0.0105 (8)	0.0005 (10)
C33	0.0432 (12)	0.104 (2)	0.0555 (14)	−0.0044 (13)	0.0165 (10)	0.0133 (15)
C34	0.0489 (13)	0.092 (2)	0.0832 (19)	−0.0194 (14)	0.0082 (13)	0.0247 (17)
C35	0.0642 (16)	0.0622 (15)	0.094 (2)	−0.0200 (13)	−0.0012 (15)	−0.0006 (15)
C36	0.0501 (12)	0.0532 (13)	0.0597 (14)	−0.0049 (10)	0.0091 (10)	−0.0086 (11)
Cl37	0.0628 (4)	0.0959 (5)	0.0929 (5)	0.0075 (3)	0.0269 (3)	−0.0442 (4)

N1—C2	1.360 (2)	C21—C22	1.385 (3)
N1—C21	1.411 (2)	C21—C26	1.388 (3)
N1—C5	1.473 (2)	C22—C23	1.383 (3)
C2—N6	1.305 (2)	C22—H221	0.97 (3)
C2—N3	1.358 (2)	C23—C24	1.362 (3)
N3—C9	1.391 (2)	C23—H231	0.90 (3)
N3—C4	1.458 (2)	C24—C25	1.373 (3)
C4—C5	1.528 (3)	C24—Cl27	1.735 (2)
C4—H41	0.99 (3)	C25—C26	1.384 (3)
C4—H42	0.99 (3)	C25—H251	0.97 (3)
C5—H51	0.99 (3)	C26—H261	0.90 (3)
C5—H52	1.04 (3)	C31—C36	1.382 (3)
N6—C7	1.361 (2)	C31—C32	1.382 (3)
C7—O10	1.330 (2)	C32—C33	1.381 (3)
C7—C8	1.379 (2)	C32—Cl37	1.740 (2)
C8—C9	1.421 (3)	C33—C34	1.364 (4)
C8—C12	1.501 (2)	C33—H331	0.93 (3)
C9—O11	1.242 (2)	C34—C35	1.374 (4)
O10—H101	0.85 (3)	C34—H341	0.95 (4)
C12—C31	1.514 (3)	C35—C36	1.388 (3)
C12—H121	1.00 (3)	C35—H351	0.97 (4)
C12—H122	0.97 (3)	C36—H361	0.93 (3)
C2—N1—C21	127.93 (15)	H121—C12—H122	105.4 (19)
C2—N1—C5	110.25 (15)	C22—C21—C26	118.77 (18)
C21—N1—C5	121.37 (15)	C22—C21—N1	118.71 (18)
N6—C2—N3	124.25 (16)	C26—C21—N1	122.50 (17)
N6—C2—N1	126.25 (16)	C23—C22—C21	120.8 (2)
N3—C2—N1	109.48 (15)	C23—C22—H221	117.5 (16)
C2—N3—C9	122.42 (15)	C21—C22—H221	121.6 (16)
C2—N3—C4	112.43 (15)	C24—C23—C22	119.7 (2)
C9—N3—C4	124.92 (15)	C24—C23—H231	120.6 (19)
N3—C4—C5	102.55 (15)	C22—C23—H231	119.7 (19)
N3—C4—H41	108.5 (15)	C23—C24—C25	120.6 (2)
C5—C4—H41	113.2 (15)	C23—C24—Cl27	119.78 (17)
N3—C4—H42	111.4 (15)	C25—C24—Cl27	119.62 (18)
C5—C4—H42	112.2 (15)	C24—C25—C26	120.2 (2)
H41—C4—H42	109 (2)	C24—C25—H251	120.1 (17)
N1—C5—C4	104.26 (16)	C26—C25—H251	119.6 (17)
N1—C5—H51	108.7 (16)	C25—C26—C21	120.0 (2)
C4—C5—H51	112.1 (16)	C25—C26—H261	118.3 (18)
N1—C5—H52	111.8 (14)	C21—C26—H261	121.7 (18)
C4—C5—H52	109.6 (14)	C36—C31—C32	116.41 (19)
H51—C5—H52	110 (2)	C36—C31—C12	123.18 (17)
C2—N6—C7	115.03 (15)	C32—C31—C12	120.40 (18)
O10—C7—N6	114.97 (15)	C33—C32—C31	122.6 (2)
O10—C7—C8	119.37 (16)	C33—C32—Cl37	117.77 (19)
N6—C7—C8	125.63 (16)	C31—C32—Cl37	119.65 (16)
C7—C8—C9	117.90 (16)	C34—C33—C32	119.8 (2)
C7—C8—C12	122.85 (17)	C34—C33—H331	122 (2)
C9—C8—C12	119.12 (15)	C32—C33—H331	118 (2)
O11—C9—N3	117.86 (16)	C33—C34—C35	119.5 (2)
O11—C9—C8	127.47 (16)	C33—C34—H341	121 (2)
N3—C9—C8	114.66 (15)	C35—C34—H341	120 (2)
C7—O10—H101	113.1 (17)	C34—C35—C36	120.1 (3)
C8—C12—C31	116.73 (16)	C34—C35—H351	122 (2)
C8—C12—H121	108.5 (14)	C36—C35—H351	118 (2)
C31—C12—H121	107.9 (14)	C31—C36—C35	121.7 (2)
C8—C12—H122	109.0 (14)	C31—C36—H361	119.5 (19)
C31—C12—H122	108.6 (14)	C35—C36—H361	118.8 (19)
C21—N1—C2—N6	−3.2 (3)	C7—C8—C12—C31	116.6 (2)
C5—N1—C2—N6	−175.39 (19)	C9—C8—C12—C31	−67.8 (2)
C21—N1—C2—N3	178.28 (17)	C2—N1—C21—C22	−164.0 (2)
C5—N1—C2—N3	6.0 (2)	C5—N1—C21—C22	7.5 (3)
N6—C2—N3—C9	−3.1 (3)	C2—N1—C21—C26	17.6 (3)
N1—C2—N3—C9	175.46 (16)	C5—N1—C21—C26	−171.0 (2)
N6—C2—N3—C4	−177.88 (19)	C26—C21—C22—C23	−0.9 (3)
N1—C2—N3—C4	0.7 (2)	N1—C21—C22—C23	−179.4 (2)
C2—N3—C4—C5	−6.7 (2)	C21—C22—C23—C24	0.3 (4)
C9—N3—C4—C5	178.73 (18)	C22—C23—C24—C25	0.6 (4)
C2—N1—C5—C4	−9.9 (2)	C22—C23—C24—Cl27	179.68 (18)
C21—N1—C5—C4	177.28 (18)	C23—C24—C25—C26	−0.9 (4)
N3—C4—C5—N1	9.5 (2)	Cl27—C24—C25—C26	180.0 (2)
N3—C2—N6—C7	0.4 (3)	C24—C25—C26—C21	0.4 (4)
N1—C2—N6—C7	−177.92 (18)	C22—C21—C26—C25	0.6 (3)
C2—N6—C7—O10	179.17 (15)	N1—C21—C26—C25	179.0 (2)
C2—N6—C7—C8	1.1 (3)	C8—C12—C31—C36	−12.0 (3)
O10—C7—C8—C9	−178.03 (16)	C8—C12—C31—C32	167.16 (18)
N6—C7—C8—C9	−0.1 (3)	C36—C31—C32—C33	0.3 (3)
O10—C7—C8—C12	−2.3 (3)	C12—C31—C32—C33	−178.9 (2)
N6—C7—C8—C12	175.65 (17)	C36—C31—C32—Cl37	−178.73 (17)
C2—N3—C9—O11	−175.20 (17)	C12—C31—C32—Cl37	2.1 (3)
C4—N3—C9—O11	−1.1 (3)	C31—C32—C33—C34	0.4 (4)
C2—N3—C9—C8	3.9 (2)	Cl37—C32—C33—C34	179.5 (2)
C4—N3—C9—C8	178.01 (19)	C32—C33—C34—C35	−1.2 (4)
C7—C8—C9—O11	176.67 (18)	C33—C34—C35—C36	1.2 (4)
C12—C8—C9—O11	0.8 (3)	C32—C31—C36—C35	−0.3 (3)
C7—C8—C9—N3	−2.4 (2)	C12—C31—C36—C35	178.9 (2)
C12—C8—C9—N3	−178.25 (16)	C34—C35—C36—C31	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H122···O10	0.97 (2)	2.41 (2)	2.848 (2)	106.5 (17)
C26—H261···N6	0.90 (2)	2.36 (2)	2.918 (3)	120.3 (19)
O10—H101···O11i	0.85 (2)	1.80 (2)	2.6418 (18)	172 (3)
C33—H331···Cl27ii	0.93 (4)	2.81 (4)	3.534 (2)	135 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H122⋯O10	0.97 (2)	2.41 (2)	2.848 (2)	106.5 (17)
C26—H261⋯N6	0.90 (2)	2.36 (2)	2.918 (3)	120.3 (19)
O10—H101⋯O11i	0.85 (2)	1.80 (2)	2.6418 (18)	172 (3)
C33—H331⋯Cl27ii	0.93 (4)	2.81 (4)	3.534 (2)	135 (3)

Symmetry codes: (i) ; (ii) .