2-(2-Hy-droxy-3-meth-oxy-phen-yl)-6H-perimidin-6-one.

The mol-ecule of the title perimidine derivative, C(18)H(12)N(2)O(3), is essentially planar, the dihedral angle between the benzene and perimidine rings being 3.25 (5)°. The hy-droxy and meth-oxy groups lie in the plane of the benzene ring to which they are bound [O-C-C-C = 179.96 (11)° and C-O-C-C = -177.96 (12)°]. An intra-molecular O-H⋯N inter-action generates an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of C-H⋯O inter-actions into dimers, which generate S(16) ring motifs. These dimers are arranged into sheets parallel to the ac plane and further stacked down the b axis by π-π inter-actions, with centroid-centroid distances in the range 3.5066 (8)-3.7241 (7) Å.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to perimidines and their applications, see: Claramunt et al. (1995 ▶); del Valle et al. (1997 ▶); Herbert et al. (1987 ▶); Llamas-Saiz et al. (1995 ▶); Pozharskii & Dalnikovskaya (1981 ▶); Varsha et al. (2010 ▶). For related structures, see: Llamas-Saiz et al. (1995 ▶); Varsha et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H12N2O3

M = 304.30

Monoclinic,

a = 25.4718 (17) Å

b = 7.0666 (3) Å

c = 15.0815 (6) Å

β = 94.373 (3)°

V = 2706.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.67 × 0.11 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.933, T max = 0.994

42939 measured reflections

6529 independent reflections

3471 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.210

S = 1.02

6529 reflections

255 parameters

All H-atom parameters refined

Δρmax = 0.57 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: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006465/sj5107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006465/sj5107Isup2.hkl

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

C18H12N2O3	F(000) = 1264
Mr = 304.30	Dx = 1.493 Mg m−3
Monoclinic, C2/c	Melting point = 507–508 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.4718 (17) Å	Cell parameters from 6529 reflections
b = 7.0666 (3) Å	θ = 1.6–36.3°
c = 15.0815 (6) Å	µ = 0.10 mm−1
β = 94.373 (3)°	T = 100 K
V = 2706.8 (2) Å3	Needle, purple
Z = 8	0.67 × 0.11 × 0.05 mm

Bruker APEX DUO CCD area-detector diffractometer	6529 independent reflections
Radiation source: sealed tube	3471 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 36.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −42→34
Tmin = 0.933, Tmax = 0.994	k = −11→11
42939 measured reflections	l = −24→25

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.110P)2] where P = (Fo2 + 2Fc2)/3
6529 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 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
O1	1.20986 (4)	0.86652 (17)	0.36853 (7)	0.0390 (3)
O2	0.93604 (4)	0.76137 (15)	0.66009 (7)	0.0305 (2)
H1O2	0.9692 (9)	0.784 (3)	0.6441 (15)	0.068 (7)*
O3	0.83728 (4)	0.69274 (15)	0.67439 (7)	0.0307 (2)
N1	1.00314 (4)	0.71962 (15)	0.40931 (7)	0.0230 (2)
N2	1.01534 (4)	0.77988 (14)	0.56606 (7)	0.0217 (2)
C1	0.92971 (5)	0.68964 (16)	0.50224 (9)	0.0213 (2)
C2	0.90819 (5)	0.70778 (17)	0.58472 (9)	0.0229 (3)
C3	0.85404 (5)	0.66982 (18)	0.59105 (9)	0.0245 (3)
C4	0.82297 (5)	0.61425 (18)	0.51641 (10)	0.0269 (3)
H4	0.7846 (8)	0.588 (3)	0.5190 (13)	0.053 (5)*
C5	0.84470 (5)	0.59241 (19)	0.43503 (9)	0.0271 (3)
H5	0.8242 (6)	0.542 (2)	0.3839 (11)	0.032 (4)*
C6	0.89730 (5)	0.62922 (18)	0.42762 (9)	0.0242 (3)
H6	0.9121 (6)	0.608 (3)	0.3716 (12)	0.039 (5)*
C7	0.98576 (5)	0.73220 (16)	0.49261 (9)	0.0208 (2)
C8	1.05351 (5)	0.75829 (17)	0.40160 (9)	0.0222 (2)
C9	1.07449 (5)	0.7429 (2)	0.31468 (9)	0.0271 (3)
H9	1.0495 (6)	0.696 (2)	0.2625 (11)	0.027 (4)*
C10	1.12551 (5)	0.7780 (2)	0.30472 (9)	0.0281 (3)
H10	1.1420 (6)	0.761 (2)	0.2446 (11)	0.031 (4)*
C11	1.16293 (5)	0.83502 (19)	0.37912 (9)	0.0269 (3)
C12	1.14203 (5)	0.84961 (17)	0.46741 (9)	0.0233 (3)
C13	1.17405 (5)	0.89476 (19)	0.54295 (9)	0.0268 (3)
H13	1.2155 (6)	0.916 (2)	0.5341 (11)	0.032*
C14	1.15283 (5)	0.90293 (19)	0.62651 (10)	0.0284 (3)
H14	1.1753 (6)	0.931 (2)	0.6784 (10)	0.029 (4)*
C15	1.10056 (5)	0.86583 (18)	0.63559 (9)	0.0257 (3)
H15	1.0859 (6)	0.865 (2)	0.6931 (12)	0.036 (4)*
C16	1.06736 (5)	0.81935 (16)	0.55893 (9)	0.0218 (2)
C17	1.08818 (5)	0.81121 (16)	0.47560 (8)	0.0206 (2)
C18	0.78320 (6)	0.6497 (2)	0.68447 (12)	0.0338 (3)
H18A	0.7621 (7)	0.737 (3)	0.6464 (12)	0.039 (5)*
H18B	0.7746 (6)	0.521 (3)	0.6683 (10)	0.032 (4)*
H18C	0.7805 (7)	0.666 (2)	0.7467 (12)	0.035 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0255 (5)	0.0525 (7)	0.0408 (6)	−0.0050 (5)	0.0157 (4)	0.0022 (5)
O2	0.0225 (5)	0.0393 (6)	0.0313 (5)	−0.0060 (4)	0.0121 (4)	−0.0095 (4)
O3	0.0201 (4)	0.0387 (6)	0.0353 (5)	−0.0036 (4)	0.0158 (4)	−0.0050 (4)
N1	0.0213 (5)	0.0227 (5)	0.0261 (6)	0.0006 (4)	0.0090 (4)	0.0043 (4)
N2	0.0189 (5)	0.0195 (5)	0.0278 (6)	−0.0018 (4)	0.0099 (4)	−0.0012 (4)
C1	0.0201 (5)	0.0168 (5)	0.0282 (6)	0.0001 (4)	0.0088 (5)	0.0031 (4)
C2	0.0204 (6)	0.0202 (5)	0.0290 (7)	−0.0007 (4)	0.0089 (5)	−0.0003 (4)
C3	0.0222 (6)	0.0220 (5)	0.0309 (7)	0.0002 (4)	0.0112 (5)	0.0011 (5)
C4	0.0186 (6)	0.0244 (6)	0.0383 (8)	−0.0017 (5)	0.0073 (5)	0.0059 (5)
C5	0.0235 (6)	0.0268 (6)	0.0313 (7)	−0.0019 (5)	0.0036 (5)	0.0066 (5)
C6	0.0245 (6)	0.0234 (6)	0.0254 (6)	−0.0002 (4)	0.0066 (5)	0.0054 (5)
C7	0.0213 (5)	0.0171 (5)	0.0253 (6)	0.0013 (4)	0.0092 (5)	0.0019 (4)
C8	0.0212 (5)	0.0196 (5)	0.0266 (6)	0.0013 (4)	0.0079 (5)	0.0041 (4)
C9	0.0265 (6)	0.0316 (6)	0.0244 (6)	0.0006 (5)	0.0096 (5)	0.0042 (5)
C10	0.0273 (6)	0.0330 (7)	0.0254 (7)	0.0006 (5)	0.0118 (5)	0.0051 (5)
C11	0.0249 (6)	0.0271 (6)	0.0304 (7)	0.0000 (5)	0.0127 (5)	0.0043 (5)
C12	0.0204 (5)	0.0213 (5)	0.0297 (6)	−0.0008 (4)	0.0109 (5)	0.0026 (5)
C13	0.0219 (6)	0.0261 (6)	0.0336 (7)	−0.0046 (5)	0.0090 (5)	0.0000 (5)
C14	0.0248 (6)	0.0295 (6)	0.0319 (7)	−0.0057 (5)	0.0077 (5)	−0.0041 (5)
C15	0.0245 (6)	0.0263 (6)	0.0273 (7)	−0.0051 (5)	0.0100 (5)	−0.0033 (5)
C16	0.0211 (5)	0.0175 (5)	0.0281 (6)	−0.0020 (4)	0.0104 (4)	−0.0016 (4)
C17	0.0210 (5)	0.0168 (5)	0.0253 (6)	0.0000 (4)	0.0094 (4)	0.0024 (4)
C18	0.0192 (6)	0.0437 (9)	0.0405 (9)	−0.0047 (6)	0.0145 (6)	−0.0017 (7)

O1—C11	1.2384 (16)	C8—C17	1.4196 (18)
O2—C2	1.3474 (16)	C8—C9	1.4568 (19)
O2—H1O2	0.91 (2)	C9—C10	1.3427 (19)
O3—C3	1.3676 (16)	C9—H9	1.028 (16)
O3—C18	1.4301 (16)	C10—C11	1.472 (2)
N1—C8	1.3256 (16)	C10—H10	1.035 (17)
N1—C7	1.3663 (17)	C11—C12	1.4747 (18)
N2—C7	1.3345 (17)	C12—C13	1.3868 (19)
N2—C16	1.3664 (16)	C12—C17	1.4127 (17)
C1—C2	1.4030 (18)	C13—C14	1.4098 (19)
C1—C6	1.4102 (19)	C13—H13	1.085 (16)
C1—C7	1.4769 (17)	C14—C15	1.3739 (18)
C2—C3	1.4155 (17)	C14—H14	0.955 (15)
C3—C4	1.3827 (19)	C15—C16	1.4179 (18)
C4—C5	1.393 (2)	C15—H15	0.970 (17)
C4—H4	1.000 (19)	C16—C17	1.4019 (18)
C5—C6	1.3777 (18)	C18—H18A	0.976 (18)
C5—H5	0.966 (16)	C18—H18B	0.963 (17)
C6—H6	0.963 (18)	C18—H18C	0.954 (18)
C2—O2—H1O2	105.4 (14)	C9—C10—C11	122.77 (12)
C3—O3—C18	116.32 (11)	C9—C10—H10	122.6 (9)
C8—N1—C7	116.80 (11)	C11—C10—H10	114.6 (9)
C7—N2—C16	118.40 (11)	O1—C11—C10	121.75 (12)
C2—C1—C6	119.38 (11)	O1—C11—C12	121.49 (13)
C2—C1—C7	120.97 (11)	C10—C11—C12	116.75 (11)
C6—C1—C7	119.65 (11)	C13—C12—C17	119.11 (12)
O2—C2—C1	123.88 (11)	C13—C12—C11	121.84 (12)
O2—C2—C3	116.70 (11)	C17—C12—C11	119.03 (12)
C1—C2—C3	119.41 (12)	C12—C13—C14	120.14 (12)
O3—C3—C4	125.62 (12)	C12—C13—H13	116.6 (8)
O3—C3—C2	114.43 (12)	C14—C13—H13	123.2 (8)
C4—C3—C2	119.95 (12)	C15—C14—C13	121.45 (13)
C3—C4—C5	120.50 (12)	C15—C14—H14	118.9 (9)
C3—C4—H4	121.5 (11)	C13—C14—H14	119.6 (9)
C5—C4—H4	118.0 (11)	C14—C15—C16	119.02 (12)
C6—C5—C4	120.32 (13)	C14—C15—H15	122.2 (10)
C6—C5—H5	118.3 (9)	C16—C15—H15	118.7 (10)
C4—C5—H5	121.2 (9)	N2—C16—C17	119.84 (11)
C5—C6—C1	120.42 (12)	N2—C16—C15	120.32 (11)
C5—C6—H6	119.3 (10)	C17—C16—C15	119.84 (11)
C1—C6—H6	120.2 (10)	C16—C17—C12	120.44 (12)
N2—C7—N1	125.29 (11)	C16—C17—C8	117.41 (11)
N2—C7—C1	117.29 (11)	C12—C17—C8	122.12 (11)
N1—C7—C1	117.42 (11)	O3—C18—H18A	107.1 (10)
N1—C8—C17	122.25 (12)	O3—C18—H18B	112.2 (9)
N1—C8—C9	119.17 (12)	H18A—C18—H18B	110.1 (14)
C17—C8—C9	118.57 (11)	O3—C18—H18C	102.7 (10)
C10—C9—C8	120.76 (13)	H18A—C18—H18C	115.0 (15)
C10—C9—H9	121.4 (9)	H18B—C18—H18C	109.5 (14)
C8—C9—H9	117.7 (9)
C6—C1—C2—O2	178.87 (11)	C8—C9—C10—C11	−0.6 (2)
C7—C1—C2—O2	−0.90 (19)	C9—C10—C11—O1	179.92 (13)
C6—C1—C2—C3	−1.62 (18)	C9—C10—C11—C12	1.0 (2)
C7—C1—C2—C3	178.60 (10)	O1—C11—C12—C13	−1.6 (2)
C18—O3—C3—C4	1.88 (19)	C10—C11—C12—C13	177.40 (12)
C18—O3—C3—C2	−177.96 (12)	O1—C11—C12—C17	−179.71 (12)
O2—C2—C3—O3	−0.19 (17)	C10—C11—C12—C17	−0.76 (17)
C1—C2—C3—O3	−179.73 (10)	C17—C12—C13—C14	−0.32 (19)
O2—C2—C3—C4	179.96 (11)	C11—C12—C13—C14	−178.48 (12)
C1—C2—C3—C4	0.42 (18)	C12—C13—C14—C15	0.4 (2)
O3—C3—C4—C5	−178.86 (12)	C13—C14—C15—C16	−0.3 (2)
C2—C3—C4—C5	0.98 (19)	C7—N2—C16—C17	0.73 (17)
C3—C4—C5—C6	−1.1 (2)	C7—N2—C16—C15	−178.36 (11)
C4—C5—C6—C1	−0.1 (2)	C14—C15—C16—N2	179.33 (12)
C2—C1—C6—C5	1.47 (18)	C14—C15—C16—C17	0.24 (19)
C7—C1—C6—C5	−178.75 (11)	N2—C16—C17—C12	−179.29 (10)
C16—N2—C7—N1	−0.21 (18)	C15—C16—C17—C12	−0.20 (18)
C16—N2—C7—C1	179.80 (10)	N2—C16—C17—C8	−0.99 (17)
C8—N1—C7—N2	−0.03 (18)	C15—C16—C17—C8	178.10 (11)
C8—N1—C7—C1	179.96 (10)	C13—C12—C17—C16	0.24 (18)
C2—C1—C7—N2	2.97 (17)	C11—C12—C17—C16	178.45 (10)
C6—C1—C7—N2	−176.80 (11)	C13—C12—C17—C8	−177.98 (11)
C2—C1—C7—N1	−177.02 (10)	C11—C12—C17—C8	0.23 (18)
C6—C1—C7—N1	3.21 (16)	N1—C8—C17—C16	0.77 (17)
C7—N1—C8—C17	−0.26 (17)	C9—C8—C17—C16	−178.10 (11)
C7—N1—C8—C9	178.60 (11)	N1—C8—C17—C12	179.04 (11)
N1—C8—C9—C10	−178.90 (12)	C9—C8—C17—C12	0.17 (17)
C17—C8—C9—C10	0.01 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.91 (2)	1.73 (2)	2.5583 (15)	151 (2)
C15—H15···O2i	0.970 (18)	2.437 (18)	3.3686 (17)	160.8 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.91 (2)	1.73 (2)	2.5583 (15)	151 (2)
C15—H15⋯O2i	0.970 (18)	2.437 (18)	3.3686 (17)	160.8 (12)

Symmetry code: (i) .