4-Phenyl-1,2,3,4-tetra-hydro-pyrimido[1,2-a]benzimidazol-2-one.

In the title compound, C(16)H(13)N(3)O, the tetrahydropyrimidin-one ring adopts a sofa conformation. In the crystal structure, mol-ecules are linked by N-H⋯N hydrogen bonds and C-H⋯π inter-actions.

Related literature

For background information on the biological activities of derivatives of benzo[4,5]imidazo[1,2-a]pyrimidine, see: Abdel-Hafez (2007 ▶); Cheung et al. (2002 ▶); Nunes, Zhu, Amouzegh et al. (2005 ▶); Nunes, Zhu, Ermann et al. (2005 ▶).

Experimental

Crystal data

C16H13N3O

M = 263.29

Orthorhombic,

a = 13.606 (3) Å

b = 7.5674 (15) Å

c = 24.578 (5) Å

V = 2530.6 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 (2) K

0.18 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ▶) T min = 0.984, T max = 0.989

18521 measured reflections

2232 independent reflections

2075 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.112

S = 1.15

2232 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033497/bt2811sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033497/bt2811Isup2.hkl

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

C16H13N3O	Dx = 1.382 Mg m−3
Mr = 263.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5932 reflections
a = 13.606 (3) Å	θ = 1.5–27.9°
b = 7.5674 (15) Å	µ = 0.09 mm−1
c = 24.578 (5) Å	T = 113 K
V = 2530.6 (9) Å3	Block, colourless
Z = 8	0.18 × 0.16 × 0.12 mm
F(000) = 1104

Rigaku Saturn diffractometer	2232 independent reflections
Radiation source: rotating anode	2075 reflections with I > 2σ(I)
confocal	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	h = −14→16
Tmin = 0.984, Tmax = 0.989	k = −9→9
18521 measured reflections	l = −29→29

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.7741P] where P = (Fo2 + 2Fc2)/3
2232 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.28 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.

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 > 2sigma(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	1.17082 (8)	−0.08466 (14)	0.37667 (4)	0.0259 (3)
N1	1.05925 (9)	0.04671 (16)	0.43091 (5)	0.0194 (3)
N2	0.98285 (9)	0.31430 (15)	0.40471 (4)	0.0169 (3)
N3	0.95726 (9)	0.21752 (16)	0.48971 (5)	0.0174 (3)
C1	1.11740 (10)	0.0412 (2)	0.38584 (6)	0.0197 (3)
C2	1.11420 (10)	0.2022 (2)	0.34972 (6)	0.0207 (3)
H2A	1.1314	0.1673	0.3130	0.025*
H2B	1.1635	0.2856	0.3621	0.025*
C3	1.01412 (10)	0.29573 (19)	0.34843 (5)	0.0183 (3)
H3	1.0234	0.4141	0.3331	0.022*
C4	1.00072 (10)	0.18918 (18)	0.44299 (5)	0.0168 (3)
C5	0.93882 (10)	0.19885 (19)	0.31400 (6)	0.0187 (3)
C6	0.93352 (11)	0.2371 (2)	0.25863 (6)	0.0225 (4)
H6	0.9748	0.3225	0.2438	0.027*
C7	0.86734 (12)	0.1491 (2)	0.22546 (6)	0.0257 (4)
H7	0.8639	0.1764	0.1886	0.031*
C8	0.80641 (11)	0.0207 (2)	0.24712 (6)	0.0261 (4)
H8	0.7624	−0.0392	0.2248	0.031*
C9	0.81109 (11)	−0.0182 (2)	0.30193 (6)	0.0259 (4)
H9	0.7702	−0.1045	0.3165	0.031*
C10	0.87656 (11)	0.0711 (2)	0.33525 (6)	0.0229 (4)
H10	0.8788	0.0451	0.3722	0.028*
C11	0.92020 (10)	0.43649 (18)	0.42860 (6)	0.0169 (3)
C12	0.87700 (10)	0.58958 (19)	0.40932 (6)	0.0211 (3)
H12	0.8868	0.6287	0.3739	0.025*
C13	0.81828 (11)	0.6814 (2)	0.44562 (6)	0.0239 (4)
H13	0.7873	0.7846	0.4343	0.029*
C14	0.80457 (11)	0.6224 (2)	0.49899 (6)	0.0220 (4)
H14	0.7646	0.6873	0.5223	0.026*
C15	0.84877 (10)	0.47015 (19)	0.51797 (6)	0.0189 (3)
H15	0.8403	0.4329	0.5537	0.023*
C16	0.90620 (10)	0.37505 (19)	0.48182 (5)	0.0164 (3)
H1	1.0597 (14)	−0.043 (2)	0.4548 (6)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (6)	0.0282 (6)	0.0246 (6)	0.0092 (5)	0.0023 (4)	−0.0037 (5)
N1	0.0215 (7)	0.0183 (7)	0.0185 (6)	0.0044 (5)	0.0020 (5)	0.0009 (5)
N2	0.0180 (6)	0.0174 (6)	0.0154 (6)	0.0013 (5)	0.0003 (5)	−0.0006 (5)
N3	0.0171 (6)	0.0169 (7)	0.0182 (6)	0.0007 (5)	0.0000 (5)	−0.0007 (5)
C1	0.0158 (7)	0.0241 (8)	0.0192 (7)	0.0005 (6)	−0.0014 (6)	−0.0036 (6)
C2	0.0171 (7)	0.0247 (8)	0.0202 (7)	−0.0016 (6)	0.0021 (6)	−0.0015 (6)
C3	0.0197 (7)	0.0190 (8)	0.0161 (7)	−0.0006 (6)	0.0030 (5)	0.0007 (6)
C4	0.0151 (7)	0.0169 (7)	0.0184 (7)	−0.0004 (5)	−0.0015 (5)	−0.0009 (5)
C5	0.0174 (7)	0.0192 (8)	0.0195 (7)	0.0041 (5)	0.0010 (6)	−0.0009 (6)
C6	0.0263 (8)	0.0209 (8)	0.0204 (7)	0.0035 (6)	0.0023 (6)	0.0024 (6)
C7	0.0313 (9)	0.0273 (8)	0.0186 (7)	0.0087 (7)	−0.0048 (6)	−0.0012 (6)
C8	0.0240 (8)	0.0237 (8)	0.0306 (8)	0.0057 (6)	−0.0082 (6)	−0.0069 (7)
C9	0.0220 (8)	0.0252 (8)	0.0303 (8)	−0.0023 (6)	−0.0007 (6)	−0.0012 (6)
C10	0.0225 (8)	0.0264 (8)	0.0199 (7)	−0.0009 (6)	−0.0001 (6)	0.0022 (6)
C11	0.0136 (7)	0.0170 (7)	0.0200 (7)	−0.0018 (5)	−0.0016 (5)	−0.0024 (6)
C12	0.0209 (8)	0.0199 (8)	0.0224 (7)	−0.0003 (6)	−0.0022 (6)	0.0021 (6)
C13	0.0221 (8)	0.0179 (8)	0.0316 (8)	0.0039 (6)	−0.0032 (6)	0.0009 (6)
C14	0.0169 (7)	0.0200 (8)	0.0291 (8)	0.0014 (6)	0.0007 (6)	−0.0054 (6)
C15	0.0162 (7)	0.0199 (8)	0.0208 (7)	−0.0029 (6)	0.0000 (6)	−0.0025 (6)
C16	0.0141 (7)	0.0154 (7)	0.0197 (7)	−0.0019 (5)	−0.0019 (5)	−0.0007 (5)

O1—C1	1.2192 (18)	C6—H6	0.9300
N1—C1	1.3619 (18)	C7—C8	1.384 (2)
N1—C4	1.3728 (18)	C7—H7	0.9300
N1—H1	0.901 (9)	C8—C9	1.380 (2)
N2—C4	1.3568 (18)	C8—H8	0.9300
N2—C11	1.3879 (18)	C9—C10	1.386 (2)
N2—C3	1.4541 (17)	C9—H9	0.9300
N3—C4	1.3091 (18)	C10—H10	0.9300
N3—C16	1.3933 (19)	C11—C12	1.383 (2)
C1—C2	1.508 (2)	C11—C16	1.4013 (19)
C2—C3	1.535 (2)	C12—C13	1.385 (2)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.398 (2)
C3—C5	1.518 (2)	C13—H13	0.9300
C3—H3	0.9800	C14—C15	1.381 (2)
C5—C10	1.388 (2)	C14—H14	0.9300
C5—C6	1.393 (2)	C15—C16	1.385 (2)
C6—C7	1.385 (2)	C15—H15	0.9300
C1—N1—C4	122.48 (12)	C8—C7—C6	120.03 (14)
C1—N1—H1	120.3 (13)	C8—C7—H7	120.0
C4—N1—H1	117.2 (13)	C6—C7—H7	120.0
C4—N2—C11	106.36 (11)	C9—C8—C7	119.84 (14)
C4—N2—C3	122.67 (12)	C9—C8—H8	120.1
C11—N2—C3	130.28 (12)	C7—C8—H8	120.1
C4—N3—C16	104.09 (11)	C8—C9—C10	120.16 (15)
O1—C1—N1	121.37 (14)	C8—C9—H9	119.9
O1—C1—C2	122.66 (13)	C10—C9—H9	119.9
N1—C1—C2	115.93 (12)	C9—C10—C5	120.64 (14)
C1—C2—C3	114.22 (12)	C9—C10—H10	119.7
C1—C2—H2A	108.7	C5—C10—H10	119.7
C3—C2—H2A	108.7	C12—C11—N2	132.40 (13)
C1—C2—H2B	108.7	C12—C11—C16	122.69 (13)
C3—C2—H2B	108.7	N2—C11—C16	104.91 (12)
H2A—C2—H2B	107.6	C11—C12—C13	116.43 (14)
N2—C3—C5	112.30 (11)	C11—C12—H12	121.8
N2—C3—C2	106.53 (11)	C13—C12—H12	121.8
C5—C3—C2	112.82 (12)	C12—C13—C14	121.39 (14)
N2—C3—H3	108.3	C12—C13—H13	119.3
C5—C3—H3	108.3	C14—C13—H13	119.3
C2—C3—H3	108.3	C15—C14—C13	121.71 (14)
N3—C4—N2	114.39 (12)	C15—C14—H14	119.1
N3—C4—N1	125.47 (13)	C13—C14—H14	119.1
N2—C4—N1	120.13 (12)	C14—C15—C16	117.56 (13)
C10—C5—C6	118.75 (13)	C14—C15—H15	121.2
C10—C5—C3	122.61 (13)	C16—C15—H15	121.2
C6—C5—C3	118.62 (13)	C15—C16—N3	129.56 (13)
C7—C6—C5	120.56 (14)	C15—C16—C11	120.20 (13)
C7—C6—H6	119.7	N3—C16—C11	110.24 (12)
C5—C6—H6	119.7
C4—N1—C1—O1	177.97 (13)	C5—C6—C7—C8	−0.6 (2)
C4—N1—C1—C2	0.3 (2)	C6—C7—C8—C9	0.6 (2)
O1—C1—C2—C3	149.84 (14)	C7—C8—C9—C10	0.0 (2)
N1—C1—C2—C3	−32.47 (18)	C8—C9—C10—C5	−0.7 (2)
C4—N2—C3—C5	87.47 (16)	C6—C5—C10—C9	0.7 (2)
C11—N2—C3—C5	−81.67 (17)	C3—C5—C10—C9	−177.88 (14)
C4—N2—C3—C2	−36.51 (17)	C4—N2—C11—C12	−179.39 (15)
C11—N2—C3—C2	154.34 (14)	C3—N2—C11—C12	−8.9 (2)
C1—C2—C3—N2	47.56 (15)	C4—N2—C11—C16	1.18 (15)
C1—C2—C3—C5	−76.11 (15)	C3—N2—C11—C16	171.67 (13)
C16—N3—C4—N2	−0.06 (16)	N2—C11—C12—C13	−179.24 (14)
C16—N3—C4—N1	−179.26 (13)	C16—C11—C12—C13	0.1 (2)
C11—N2—C4—N3	−0.74 (16)	C11—C12—C13—C14	0.6 (2)
C3—N2—C4—N3	−172.13 (12)	C12—C13—C14—C15	0.0 (2)
C11—N2—C4—N1	178.50 (12)	C13—C14—C15—C16	−1.2 (2)
C3—N2—C4—N1	7.1 (2)	C14—C15—C16—N3	−178.84 (13)
C1—N1—C4—N3	−166.90 (14)	C14—C15—C16—C11	1.8 (2)
C1—N1—C4—N2	13.9 (2)	C4—N3—C16—C15	−178.53 (14)
N2—C3—C5—C10	−30.14 (19)	C4—N3—C16—C11	0.85 (15)
C2—C3—C5—C10	90.27 (16)	C12—C11—C16—C15	−1.3 (2)
N2—C3—C5—C6	151.27 (13)	N2—C11—C16—C15	178.17 (12)
C2—C3—C5—C6	−88.32 (16)	C12—C11—C16—N3	179.23 (12)
C10—C5—C6—C7	0.0 (2)	N2—C11—C16—N3	−1.28 (15)
C3—C5—C6—C7	178.60 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.90 (1)	1.91 (1)	2.8027 (17)	171 (2)
C13—H13···Cgii	0.93	2.85	3.6296 (18)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.901 (9)	1.909 (10)	2.8027 (17)	171.0 (19)
C13—H13⋯Cgii	0.93	2.85	3.6296 (18)	143

Symmetry codes: (i) ; (ii) .