2-(2-Hydroxy­ethyl­amino)-3-phenyl-1-benzofuro[3,2-d]pyrimidin-4(3H)-one dichloro­methane hemisolvate

Zhang, Z.-H.; Liu, X.-L.; Chen, L.-J.

doi:10.1107/S1600536809017814

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1330

doi:10.1107/S1600536809017814

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2-(2-Hydroxyethylamino)-3-phenyl-1-benzofuro[3,2-d]pyrimidin-4(3H)-one dichloromethane hemisolvate

Zheng-Hong Zhang,^a,^b ^* Xiao-Ling Liu ^c and Long-Ju Chen ^b

^aDepartment of Neurology, Affiliated Renmin Hospital, Yunyang Medical College, Shiyan 442000, People's Republic of China, ^bDepartment of Human Anatomy, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^cDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: zhangzh8875301@yahoo.com.cn

(Received 7 May 2009; accepted 12 May 2009; online 20 May 2009)

In the title compound, C₁₈H₁₅N₃O₃·0.5CH₂Cl₂, the fused ring benzofuro[2,3-d]pyrimidine system is essentially planar [maximum deviation 0.029 (1) Å]. The planes of the pyrimidinone and phenyl rings are nearly perpendicular [dihedral angle = 87.50 (14)°]. The packing of the molecules in the crystal structure is governed mainly by intermolecular O—H⋯O and N—H⋯O hydrogen-bonding interactions and intermolecular π–π interactions between benzofuro[3,2-d]pyrimidine units [the interplanar distances are ca 3.4 and 3.5 Å, and the distances between adjacent ring centroids are in the range 3.64 (1)–3.76 (1) Å]. The dichloromethane solvent molecule lies on a special position.

Related literature

For the preparation and biological activity of benzofuropyrimidine derivatives, see: Moneam et al. (2004 ); Bodke et al. (2003 ). For π-π stacking interactions, see: Hu et al. (2005 , 2006 , 2007 , 2008 ); Janiak (2000 ). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007, 2008).

Experimental

Crystal data

C₁₈H₁₅N₃O₃·0.5CH₂Cl₂
M_r = 363.80
Monoclinic, C 2/c
a = 26.928 (2) Å
b = 7.8931 (7) Å
c = 17.3134 (15) Å
β = 110.638 (2)°
V = 3443.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.941, T_max = 0.960
6773 measured reflections
3008 independent reflections
2321 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.203
S = 1.04
3008 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O3ⁱ	0.86	2.23	2.903 (3)	136
O3—H3A⋯O2ⁱⁱ	0.82	1.94	2.744 (3)	167
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017814/at2780sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017814/at2780Isup2.hkl

checkCIF report

Comment top

Derivatives of benzofuropyrimidines are of great importance because of their remarkable biological properties, such as the interesting analgesic, antihypertensive, antipyretic, antiviral, and anti-inflammatory activities (Moneam et al., 2004 and Bodke et al., 2003). Some X-ray crystal structures of benzofuro[3,2-d]pyrimidinone derivatives have been reported (Hu et al., 2005, 2006, 2007, 2008). The heterocyclic title compound (I) may be used as a new precursor for obtaining bioactive molecules and its structure is presented here (Fig.1).

In the molecule of (I), all ring atoms of benzofuro[2,3-d]pyrimidine system are essentially coplanar, with maximum deviations -0.029 (1)Å and 0.027 (2) Å for C7 and N2, respectively. The pyrimidinone ring and the phenyl (C14—C19) ring are nearly perpendicular [dihedral angle = 87.50 (14)]. Intermolecular O—H···O and N—H···O hydrogen-bonding interactions (Table 1) link the molecules, helping to stabilize the crystal structure. Further stability the crystal structure is provided by offset π-π stacking interactions (Janiak, 2000) involving the fused benzofuro[2,3-d]pyrimidin system moeties. The interplanar distance are ca 3.5 Å, with distances between adjacent ring centroids of 3.6 (1)–3.8 (1)Å [symmetry code relating the adjacent rings: -x, 2 - y, -z].

Related literature top

For the preparation and biological activity of benzofuropyrimidine derivatives, see: Moneam et al. (2004); Bodke et al. (2003). For π-π stacking interactions, see: Hu et al. (2005, 2006, 2007, 2008); Janiak (2000). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007, 2008).

Experimental top

For background references, see: Hu et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at 50% probability level. [Symmetry code: (a) -x, y, -z +3/2].
	Fig. 2. A partial view of the crystal packing of the title compound, showing the hydrogen-bonded stacking interactions (dashed lines).

2-(2-Hydroxyethylamino)-3-phenyl-1-benzofuro[3,2-d]pyrimidin- 4(3H)-one dichloromethane hemisolvate top

Crystal data top

C₁₈H₁₅N₃O₃·0.5CH₂Cl₂	F(000) = 1512
M_r = 363.80	D_x = 1.403 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2289 reflections
a = 26.928 (2) Å	θ = 2.5–25.0°
b = 7.8931 (7) Å	µ = 0.25 mm⁻¹
c = 17.3134 (15) Å	T = 292 K
β = 110.638 (2)°	Needle, colourless
V = 3443.7 (5) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3008 independent reflections
Radiation source: fine-focus sealed tube	2321 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→32
T_min = 0.941, T_max = 0.960	k = −9→9
6773 measured reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.066	H-atom parameters constrained
wR(F²) = 0.203	w = 1/[σ²(F_o²) + (0.1003P)² + 4.9568P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3008 reflections	Δρ_max = 0.74 e Å⁻³
232 parameters	Δρ_min = −0.46 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (4)

Crystal data top

C₁₈H₁₅N₃O₃·0.5CH₂Cl₂	V = 3443.7 (5) Å³
M_r = 363.80	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.928 (2) Å	µ = 0.25 mm⁻¹
b = 7.8931 (7) Å	T = 292 K
c = 17.3134 (15) Å	0.30 × 0.20 × 0.20 mm
β = 110.638 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3008 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2321 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.960	R_int = 0.025
6773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.203	H-atom parameters constrained
S = 1.04	Δρ_max = 0.74 e Å⁻³
3008 reflections	Δρ_min = −0.46 e Å⁻³
232 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.00474 (12)	0.9366 (4)	0.1209 (2)	0.0562 (8)
C2	−0.04614 (14)	0.9437 (5)	0.1234 (2)	0.0724 (10)
H2	−0.0549	1.0163	0.1589	0.087*
C3	−0.08262 (14)	0.8376 (6)	0.0704 (3)	0.0828 (13)
H3	−0.1172	0.8374	0.0703	0.099*
C4	−0.06967 (14)	0.7306 (6)	0.0171 (3)	0.0772 (11)
H4	−0.0958	0.6618	−0.0185	0.093*
C5	−0.01884 (12)	0.7234 (4)	0.0155 (2)	0.0626 (9)
H5	−0.0103	0.6509	−0.0203	0.075*
C6	0.01922 (11)	0.8287 (4)	0.06958 (18)	0.0502 (7)
C7	0.07480 (11)	0.8619 (4)	0.08694 (17)	0.0456 (7)
C8	0.08819 (11)	0.9878 (4)	0.14460 (18)	0.0494 (7)
C9	0.13833 (11)	1.0657 (4)	0.17189 (17)	0.0488 (7)
C10	0.15717 (11)	0.8521 (3)	0.08219 (16)	0.0423 (7)
C11	0.18301 (12)	0.6367 (4)	0.0038 (2)	0.0534 (8)
H11A	0.1605	0.5601	0.0205	0.064*
H11B	0.2159	0.5778	0.0106	0.064*
C12	0.15587 (12)	0.6799 (5)	−0.0862 (2)	0.0617 (9)
H12A	0.1455	0.5770	−0.1185	0.074*
H12B	0.1242	0.7464	−0.0936	0.074*
C14	0.22429 (10)	1.0652 (4)	0.15552 (16)	0.0443 (7)
C15	0.23170 (12)	1.1918 (4)	0.10617 (18)	0.0525 (8)
H15	0.2036	1.2268	0.0597	0.063*
C16	0.28099 (13)	1.2672 (4)	0.1257 (2)	0.0591 (8)
H16	0.2862	1.3529	0.0925	0.071*
C17	0.32232 (12)	1.2151 (4)	0.1946 (2)	0.0577 (8)
H17	0.3555	1.2653	0.2078	0.069*
C18	0.31458 (12)	1.0894 (4)	0.2437 (2)	0.0603 (9)
H18	0.3426	1.0553	0.2903	0.072*
C19	0.26543 (12)	1.0123 (4)	0.22476 (19)	0.0533 (8)
H19	0.2603	0.9267	0.2581	0.064*
Cl1	0.04437 (10)	0.5409 (4)	0.71999 (15)	0.1632 (11)
N1	0.10909 (9)	0.7873 (3)	0.05548 (14)	0.0463 (6)
N2	0.17227 (9)	0.9896 (3)	0.13565 (14)	0.0439 (6)
N3	0.19460 (9)	0.7832 (3)	0.05727 (14)	0.0495 (6)
H3B	0.2259	0.8269	0.0733	0.059*
O1	0.04639 (8)	1.0374 (3)	0.16786 (13)	0.0602 (6)
O2	0.15384 (9)	1.1865 (3)	0.21917 (14)	0.0665 (7)
O3	0.19168 (9)	0.7736 (4)	−0.11261 (14)	0.0768 (8)
H3A	0.1774	0.7980	−0.1615	0.115*
C20	0.0000	0.509 (3)	0.7500	0.394 (18)
H20A	0.0194	0.4328	0.7943	0.473*	0.5
H20B	−0.0194	0.4329	0.7057	0.473*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0478 (17)	0.068 (2)	0.0549 (18)	0.0005 (15)	0.0201 (14)	0.0145 (16)
C2	0.053 (2)	0.099 (3)	0.073 (2)	0.011 (2)	0.0313 (18)	0.018 (2)
C3	0.0431 (19)	0.120 (3)	0.087 (3)	−0.001 (2)	0.0251 (19)	0.029 (3)
C4	0.0456 (19)	0.093 (3)	0.084 (3)	−0.0150 (18)	0.0124 (18)	0.017 (2)
C5	0.0516 (18)	0.061 (2)	0.070 (2)	−0.0065 (15)	0.0149 (16)	0.0112 (17)
C6	0.0435 (16)	0.0517 (17)	0.0555 (17)	0.0010 (13)	0.0178 (13)	0.0140 (14)
C7	0.0438 (15)	0.0473 (16)	0.0449 (15)	−0.0002 (12)	0.0148 (12)	0.0062 (13)
C8	0.0437 (16)	0.0604 (18)	0.0476 (16)	0.0026 (13)	0.0203 (13)	0.0019 (14)
C9	0.0524 (17)	0.0546 (18)	0.0395 (15)	0.0007 (14)	0.0164 (13)	−0.0018 (14)
C10	0.0435 (15)	0.0447 (15)	0.0380 (14)	−0.0031 (12)	0.0134 (11)	0.0018 (12)
C11	0.0513 (17)	0.0456 (16)	0.068 (2)	−0.0010 (13)	0.0265 (15)	−0.0059 (15)
C12	0.0446 (17)	0.073 (2)	0.065 (2)	−0.0032 (15)	0.0161 (15)	−0.0223 (17)
C14	0.0429 (15)	0.0483 (16)	0.0417 (15)	−0.0034 (12)	0.0149 (12)	−0.0063 (13)
C15	0.0495 (17)	0.0603 (19)	0.0460 (16)	−0.0003 (14)	0.0149 (13)	0.0063 (14)
C16	0.0593 (19)	0.0572 (19)	0.067 (2)	−0.0058 (15)	0.0294 (16)	0.0038 (16)
C17	0.0450 (17)	0.0612 (19)	0.069 (2)	−0.0117 (14)	0.0225 (15)	−0.0185 (17)
C18	0.0444 (17)	0.073 (2)	0.0546 (18)	−0.0015 (15)	0.0068 (14)	−0.0076 (17)
C19	0.0525 (18)	0.0566 (18)	0.0469 (17)	−0.0055 (14)	0.0126 (14)	0.0013 (14)
Cl1	0.1220 (17)	0.241 (3)	0.1193 (16)	−0.0455 (18)	0.0331 (14)	−0.0050 (18)
N1	0.0406 (13)	0.0489 (14)	0.0493 (13)	−0.0041 (10)	0.0158 (10)	−0.0024 (11)
N2	0.0413 (13)	0.0491 (14)	0.0412 (12)	−0.0043 (10)	0.0142 (10)	−0.0030 (11)
N3	0.0408 (13)	0.0573 (15)	0.0520 (14)	−0.0054 (11)	0.0182 (11)	−0.0109 (12)
O1	0.0528 (13)	0.0745 (15)	0.0603 (13)	0.0037 (11)	0.0286 (11)	−0.0056 (11)
O2	0.0653 (14)	0.0744 (16)	0.0605 (13)	−0.0098 (12)	0.0229 (11)	−0.0266 (12)
O3	0.0628 (15)	0.110 (2)	0.0520 (13)	−0.0030 (14)	0.0131 (11)	0.0062 (13)
C20	0.137 (13)	0.56 (5)	0.44 (4)	0.000	0.038 (18)	0.000

Geometric parameters (Å, º) top

C1—O1	1.381 (4)	C11—H11A	0.9700
C1—C6	1.383 (5)	C11—H11B	0.9700
C1—C2	1.387 (5)	C12—O3	1.413 (4)
C2—C3	1.369 (6)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.383 (6)	C14—C15	1.375 (4)
C3—H3	0.9300	C14—C19	1.379 (4)
C4—C5	1.380 (5)	C14—N2	1.448 (3)
C4—H4	0.9300	C15—C16	1.383 (4)
C5—C6	1.393 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.376 (5)
C6—C7	1.443 (4)	C16—H16	0.9300
C7—N1	1.360 (3)	C17—C18	1.370 (5)
C7—C8	1.364 (4)	C17—H17	0.9300
C8—O1	1.379 (3)	C18—C19	1.387 (4)
C8—C9	1.405 (4)	C18—H18	0.9300
C9—O2	1.230 (4)	C19—H19	0.9300
C9—N2	1.412 (4)	Cl1—C20	1.483 (5)
C10—N1	1.315 (3)	N3—H3B	0.8600
C10—N3	1.343 (3)	O3—H3A	0.8200
C10—N2	1.391 (3)	C20—H20A	0.9700
C11—N3	1.445 (4)	C20—H20B	0.9700
C11—C12	1.508 (5)

O1—C1—C6	112.2 (3)	C11—C12—H12A	110.0
O1—C1—C2	124.3 (3)	O3—C12—H12B	110.0
C6—C1—C2	123.4 (3)	C11—C12—H12B	110.0
C3—C2—C1	116.0 (4)	H12A—C12—H12B	108.4
C3—C2—H2	122.0	C15—C14—C19	120.8 (3)
C1—C2—H2	122.0	C15—C14—N2	119.5 (2)
C2—C3—C4	122.1 (3)	C19—C14—N2	119.7 (3)
C2—C3—H3	119.0	C14—C15—C16	119.8 (3)
C4—C3—H3	119.0	C14—C15—H15	120.1
C5—C4—C3	121.6 (4)	C16—C15—H15	120.1
C5—C4—H4	119.2	C17—C16—C15	119.8 (3)
C3—C4—H4	119.2	C17—C16—H16	120.1
C4—C5—C6	117.5 (4)	C15—C16—H16	120.1
C4—C5—H5	121.2	C18—C17—C16	120.1 (3)
C6—C5—H5	121.2	C18—C17—H17	120.0
C1—C6—C5	119.5 (3)	C16—C17—H17	120.0
C1—C6—C7	105.1 (3)	C17—C18—C19	120.8 (3)
C5—C6—C7	135.4 (3)	C17—C18—H18	119.6
N1—C7—C8	124.5 (3)	C19—C18—H18	119.6
N1—C7—C6	129.7 (3)	C14—C19—C18	118.7 (3)
C8—C7—C6	105.8 (3)	C14—C19—H19	120.7
C7—C8—O1	112.8 (3)	C18—C19—H19	120.7
C7—C8—C9	122.7 (3)	C10—N1—C7	114.5 (2)
O1—C8—C9	124.3 (3)	C10—N2—C9	123.0 (2)
O2—C9—C8	128.6 (3)	C10—N2—C14	120.7 (2)
O2—C9—N2	120.3 (3)	C9—N2—C14	116.3 (2)
C8—C9—N2	111.1 (3)	C10—N3—C11	120.8 (2)
N1—C10—N3	119.1 (3)	C10—N3—H3B	119.6
N1—C10—N2	123.9 (2)	C11—N3—H3B	119.6
N3—C10—N2	116.9 (2)	C8—O1—C1	104.0 (2)
N3—C11—C12	113.4 (3)	C12—O3—H3A	109.5
N3—C11—H11A	108.9	Cl1—C20—Cl1ⁱ	161 (2)
C12—C11—H11A	108.9	Cl1—C20—H20A	96.0
N3—C11—H11B	108.9	Cl1ⁱ—C20—H20A	96.0
C12—C11—H11B	108.9	Cl1—C20—H20B	96.0
H11A—C11—H11B	107.7	Cl1ⁱ—C20—H20B	96.0
O3—C12—C11	108.4 (2)	H20A—C20—H20B	103.4
O3—C12—H12A	110.0

O1—C1—C2—C3	178.0 (3)	C16—C17—C18—C19	0.4 (5)
C6—C1—C2—C3	−0.8 (5)	C15—C14—C19—C18	−0.1 (5)
C1—C2—C3—C4	−0.5 (6)	N2—C14—C19—C18	−178.4 (3)
C2—C3—C4—C5	1.0 (6)	C17—C18—C19—C14	−0.2 (5)
C3—C4—C5—C6	−0.2 (5)	N3—C10—N1—C7	177.5 (2)
O1—C1—C6—C5	−177.3 (3)	N2—C10—N1—C7	−2.4 (4)
C2—C1—C6—C5	1.6 (5)	C8—C7—N1—C10	−3.2 (4)
O1—C1—C6—C7	1.3 (3)	C6—C7—N1—C10	177.5 (3)
C2—C1—C6—C7	−179.8 (3)	N1—C10—N2—C9	5.1 (4)
C4—C5—C6—C1	−1.0 (5)	N3—C10—N2—C9	−174.8 (2)
C4—C5—C6—C7	−179.1 (3)	N1—C10—N2—C14	−173.4 (3)
C1—C6—C7—N1	177.8 (3)	N3—C10—N2—C14	6.7 (4)
C5—C6—C7—N1	−3.9 (6)	O2—C9—N2—C10	179.6 (3)
C1—C6—C7—C8	−1.6 (3)	C8—C9—N2—C10	−1.9 (4)
C5—C6—C7—C8	176.7 (3)	O2—C9—N2—C14	−1.9 (4)
N1—C7—C8—O1	−178.1 (2)	C8—C9—N2—C14	176.7 (2)
C6—C7—C8—O1	1.4 (3)	C15—C14—N2—C10	88.1 (3)
N1—C7—C8—C9	6.4 (5)	C19—C14—N2—C10	−93.5 (3)
C6—C7—C8—C9	−174.1 (3)	C15—C14—N2—C9	−90.5 (3)
C7—C8—C9—O2	175.0 (3)	C19—C14—N2—C9	87.9 (3)
O1—C8—C9—O2	0.0 (5)	N1—C10—N3—C11	−1.8 (4)
C7—C8—C9—N2	−3.5 (4)	N2—C10—N3—C11	178.1 (2)
O1—C8—C9—N2	−178.4 (3)	C12—C11—N3—C10	82.1 (3)
N3—C11—C12—O3	66.0 (3)	C7—C8—O1—C1	−0.6 (3)
C19—C14—C15—C16	0.2 (5)	C9—C8—O1—C1	174.8 (3)
N2—C14—C15—C16	178.6 (3)	C6—C1—O1—C8	−0.5 (3)
C14—C15—C16—C17	−0.1 (5)	C2—C1—O1—C8	−179.4 (3)
C15—C16—C17—C18	−0.2 (5)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O3ⁱⁱ	0.86	2.23	2.903 (3)	136
O3—H3A···O2ⁱⁱⁱ	0.82	1.94	2.744 (3)	167

Symmetry codes: (ii) −x+1/2, −y+3/2, −z; (iii) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₃O₃·0.5CH₂Cl₂
M_r	363.80
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	26.928 (2), 7.8931 (7), 17.3134 (15)
β (°)	110.638 (2)
V (Å³)	3443.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.941, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	6773, 3008, 2321
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.203, 1.04
No. of reflections	3008
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.46

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O3ⁱ	0.86	2.23	2.903 (3)	135.5
O3—H3A···O2ⁱⁱ	0.82	1.94	2.744 (3)	166.7

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) x, −y+2, z−1/2.

Acknowledgements

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D200724001) and the Science Research Project of Yunyang Medical College (No. 2006QDJ16).

References

Bodke, Y. & Sangapure, S. S. (2003). J. Indian Chem. Soc. 80, 187–189. CAS Google Scholar
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, Y.-G., Li, G.-H., Tian, J.-H., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o3266–o3268. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836–o1838. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y. G., Liu, M. G. & Ding, M. W. (2008). Helv. Chim. Acta, pp. 862–872. Google Scholar
Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459. Web of Science CSD CrossRef IUCr Journals Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Moneam, M., Geies, A., El-Naggar, G. & Mousa, S. (2004). J. Chin. Chem. Soc. 51, 1357–1366. Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(2-Hy­droxy­ethyl­amino)-3-phenyl-1-benzofuro[3,2-d]pyrimidin-4(3H)-one di­chloro­methane hemisolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(2-Hydroxyethylamino)-3-phenyl-1-benzofuro[3,2-d]pyrimidin-4(3H)-one dichloromethane hemisolvate