3,3′-(1,4-Phenyl­ene)bis­[2-(propyl­amino)­benzofuro[3,2-d]pyrimidin-4(3H)-one] ethanol disolvate

Li, L.; Qu, Y.-N.; Gong, J.; Hu, Y.-G.

doi:10.1107/S160053681201375X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1282-o1283

doi:10.1107/S160053681201375X

Open

access

3,3′-(1,4-Phenylene)bis[2-(propylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one] ethanol disolvate

Li Li,^a Yong-Nian Qu,^b Jian Gong ^c and Yang-Gen Hu ^d,^b ^*

^aThe Library of Hubei University of Medicine, Shiyan 442000, People's Republic of China, ^bInstitute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, People's Republic of China, ^cInstitute of Basic Medical Sciences, Hubei University of Medicine, Shiyan 442000, People's Republic of China, and ^dDepartment of Pharmacy, Taihe Hospital of Hubei University of Medicine, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: huyangg111@yahoo.com.cn

(Received 3 March 2012; accepted 29 March 2012; online 4 April 2012)

The title compound, C₃₂H₂₈N₆O₄·2C₂H₅OH, consists of two 2-(propylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one units connected, via one of the pyrimidine N atoms, to a bridging benzene ring in the 1,4 positions. Two ethanol solvent molecules are also present. The main molecule lies on a center of symmetry located at the center of the benzene ring. The fused-ring system of the benzofuro[3,2-d]pyrimidine moiety is nearly planar (r.m.s. deviation = 0.016 Å) and forms a dihedral angle of 78.21 (7)° with the central benzene ring. The crystal structure features O—H⋯O and N—H⋯O interactions. The C atoms of the propylamino side chain in the main molecule and the ethyl group in the solvent molecule are disordered over two positions, with site-occupancy factors 0.34:0.66 and 0.42:0.58, respectively.

Related literature

The title compound may be used as a precursor for obtaining bioactive molecules with antitumor activity, see: Bellarosa et al. (1996). For the biological activity of benzofuropyrimidine derivatives, see: Moneam et al. (2004 ); Bodke & Sangapure (2003 ). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 , 2006 , 2007 , 2008 ).

Experimental

Crystal data

C₃₂H₂₈N₆O₄·2C₂H₆O
M_r = 652.74
Monoclinic, P 2₁ /n
a = 10.1933 (12) Å
b = 13.6224 (16) Å
c = 12.5249 (15) Å
β = 105.409 (2)°
V = 1676.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.14 × 0.12 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.988, T_max = 0.991
10883 measured reflections
2941 independent reflections
2327 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.151
S = 1.03
2941 reflections
259 parameters
60 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3a⋯O3	0.86	2.22	2.996 (3)	150
O3—H3b⋯O1ⁱ	0.82	2.12	2.903 (3)	159
Symmetry code: (i) -x+1, -y, -z+1.

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/S160053681201375X/lr2054sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201375X/lr2054Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201375X/lr2054Isup3.cml

checkCIF report

Comment top

As a part of our ongoing work in the preparation of derivatives of heterocyclic compounds (Hu et al., 2005, 2006, 2007, 2008), we have synthesized and structurally characterized the title compound (Fig. 1). Here we wish to report an X-ray crystal structure of it (Fig. 1). In the molecule, the fused rings system of the benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar (r.m.s. deviation= 0.016 A°), forming a dihedral angle of 78.21 (7)° with the (C1/C2/C3/C1a/C2a/C3a) phenyl ring . The crystal structure is stabilize by O—H···O and N—H···O hydrogen bonds. The C atoms of the propylamino side chain in molecule and the ethyl in solvent molecule are disordered over two positions, with site occupancy factors 0.34/0.66 and 0.42/58 for the C atoms of the propyl and the ethyl, respectively.

Related literature top

The title compound may be used as a precursor for obtaining bioactive molecules, see: Bellarosa et al. (1996). For the biological activity of benzofuropyrimidine derivatives, see: Moneam et al. (2004); Bodke & Sangapure (2003). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007, 2008).

Experimental top

The compound was synthesized according to the procedures previously described in the literature (Hu et al., 2005, 2006, 2007, 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. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

3,3'-(1,4-Phenylene)bis[2-(propylamino)benzofuro[3,2-d]pyrimidin- 4(3H)-one] ethanol disolvate top

Crystal data top

C₃₂H₂₈N₆O₄·2C₂H₆O	F(000) = 692
M_r = 652.74	D_x = 1.293 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3984 reflections
a = 10.1933 (12) Å	θ = 2.3–26.6°
b = 13.6224 (16) Å	µ = 0.09 mm⁻¹
c = 12.5249 (15) Å	T = 298 K
β = 105.409 (2)°	Block, colorless
V = 1676.7 (3) Å³	0.14 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2941 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.988, T_max = 0.991	k = −13→16
10883 measured reflections	l = −14→14

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0753P)² + 0.3428P] where P = (F_o² + 2F_c²)/3
2941 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.17 e Å⁻³
60 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₂H₂₈N₆O₄·2C₂H₆O	V = 1676.7 (3) Å³
M_r = 652.74	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1933 (12) Å	µ = 0.09 mm⁻¹
b = 13.6224 (16) Å	T = 298 K
c = 12.5249 (15) Å	0.14 × 0.12 × 0.10 mm
β = 105.409 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2941 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2327 reflections with I > 2σ(I)
T_min = 0.988, T_max = 0.991	R_int = 0.060
10883 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	60 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
2941 reflections	Δρ_min = −0.23 e Å⁻³
259 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	0.6148 (2)	0.02496 (15)	0.58223 (16)	0.0567 (5)
H1	0.6919	0.0422	0.6376	0.068*
C2	0.53256 (19)	0.09654 (14)	0.52147 (15)	0.0506 (5)
C3	0.4179 (2)	0.07207 (15)	0.43955 (16)	0.0561 (5)
H3	0.3628	0.1210	0.3991	0.067*
C4	0.6653 (2)	0.24409 (15)	0.50513 (16)	0.0538 (5)
C5	0.6309 (2)	0.38471 (15)	0.58744 (16)	0.0546 (5)
C6	0.5310 (2)	0.34514 (15)	0.62721 (17)	0.0594 (6)
C7	0.4899 (2)	0.24663 (16)	0.60962 (17)	0.0588 (5)
C8	0.6399 (2)	0.48678 (14)	0.62188 (17)	0.0587 (6)
C9	0.5417 (3)	0.49804 (15)	0.67922 (18)	0.0654 (6)
C10	0.5178 (3)	0.58535 (18)	0.7266 (2)	0.0794 (7)
H10	0.4514	0.5909	0.7647	0.095*
C11	0.5975 (3)	0.66348 (18)	0.7143 (2)	0.0870 (9)
H11	0.5855	0.7236	0.7456	0.104*
C12	0.6954 (3)	0.65482 (17)	0.6563 (2)	0.0861 (9)
H12	0.7473	0.7094	0.6494	0.103*
C13	0.7177 (3)	0.56759 (16)	0.6088 (2)	0.0727 (7)
H13	0.7827	0.5627	0.5692	0.087*
C14	0.8284 (3)	0.2270 (2)	0.3940 (3)	0.0960 (9)
H14A	0.8253	0.1882	0.3285	0.115*	0.58
H14B	0.8023	0.2933	0.3688	0.115*	0.58
H14C	0.8351	0.2980	0.3990	0.115*	0.42
H14D	0.8145	0.2068	0.3176	0.115*	0.42
C15	0.9688 (6)	0.2310 (5)	0.4575 (7)	0.118 (2)	0.58
H15A	0.9764	0.2644	0.5272	0.141*	0.58
H15B	1.0223	0.2667	0.4168	0.141*	0.58
C16	1.0198 (10)	0.1280 (6)	0.4782 (7)	0.138 (3)	0.58
H16A	0.9695	0.0943	0.5219	0.207*	0.58
H16B	1.1146	0.1289	0.5172	0.207*	0.58
H16C	1.0081	0.0946	0.4088	0.207*	0.58
C15'	0.9540 (9)	0.1753 (13)	0.4727 (13)	0.161 (6)	0.42
H15C	0.9605	0.1952	0.5483	0.194*	0.42
H15D	0.9395	0.1049	0.4682	0.194*	0.42
C16'	1.0849 (9)	0.1976 (10)	0.4471 (10)	0.149 (4)	0.42
H16D	1.1045	0.1473	0.3999	0.223*	0.42
H16E	1.1566	0.1999	0.5147	0.223*	0.42
H16F	1.0784	0.2599	0.4103	0.223*	0.42
C17	0.5680 (9)	0.0856 (5)	0.1674 (7)	0.148 (3)	0.66
H17A	0.5009	0.1024	0.2055	0.223*	0.66
H17B	0.5254	0.0807	0.0894	0.223*	0.66
H17C	0.6368	0.1356	0.1803	0.223*	0.66
C18	0.6292 (9)	−0.0070 (5)	0.2079 (5)	0.118 (2)	0.66
H18A	0.5617	−0.0588	0.1878	0.142*	0.66
H18B	0.7020	−0.0216	0.1737	0.142*	0.66
C17'	0.6268 (14)	0.0358 (14)	0.1313 (9)	0.137 (4)	0.34
H17D	0.7050	0.0778	0.1528	0.205*	0.34
H17E	0.5587	0.0665	0.0728	0.205*	0.34
H17F	0.6527	−0.0258	0.1058	0.205*	0.34
C18'	0.5711 (10)	0.0189 (12)	0.2276 (7)	0.099 (3)	0.34
H18C	0.5239	0.0772	0.2420	0.118*	0.34
H18D	0.5064	−0.0349	0.2119	0.118*	0.34
N1	0.56533 (17)	0.19870 (11)	0.54545 (13)	0.0526 (4)
N2	0.70225 (18)	0.33593 (12)	0.52685 (15)	0.0586 (5)
N3	0.7232 (2)	0.18964 (13)	0.44097 (17)	0.0680 (5)
H3A	0.6966	0.1299	0.4271	0.082*
O1	0.40323 (19)	0.20284 (12)	0.64207 (15)	0.0807 (5)
O2	0.47273 (17)	0.41186 (11)	0.68384 (13)	0.0729 (5)
O3	0.6821 (2)	−0.00452 (14)	0.32441 (15)	0.0915 (6)
H3B	0.6693	−0.0577	0.3506	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0582 (12)	0.0497 (12)	0.0530 (11)	−0.0030 (9)	−0.0011 (9)	−0.0018 (9)
C2	0.0579 (12)	0.0437 (11)	0.0488 (10)	−0.0026 (9)	0.0118 (9)	−0.0019 (8)
C3	0.0608 (12)	0.0466 (12)	0.0537 (11)	0.0037 (9)	0.0028 (9)	0.0055 (9)
C4	0.0551 (12)	0.0461 (11)	0.0563 (11)	−0.0006 (9)	0.0076 (9)	0.0007 (9)
C5	0.0603 (12)	0.0448 (11)	0.0500 (10)	−0.0001 (9)	−0.0006 (9)	0.0004 (9)
C6	0.0698 (13)	0.0472 (12)	0.0582 (12)	0.0014 (10)	0.0115 (10)	−0.0089 (9)
C7	0.0677 (13)	0.0522 (12)	0.0563 (12)	−0.0050 (11)	0.0160 (10)	−0.0041 (10)
C8	0.0683 (13)	0.0435 (11)	0.0517 (11)	0.0035 (10)	−0.0061 (10)	−0.0004 (9)
C9	0.0775 (15)	0.0475 (13)	0.0591 (12)	0.0056 (11)	−0.0028 (11)	−0.0069 (10)
C10	0.0969 (19)	0.0583 (15)	0.0710 (15)	0.0152 (13)	0.0012 (13)	−0.0132 (12)
C11	0.115 (2)	0.0478 (14)	0.0770 (17)	0.0193 (15)	−0.0122 (16)	−0.0084 (12)
C12	0.111 (2)	0.0410 (13)	0.0850 (17)	0.0000 (13)	−0.0106 (16)	0.0040 (12)
C13	0.0867 (17)	0.0468 (13)	0.0709 (14)	−0.0030 (11)	−0.0030 (12)	0.0050 (10)
C14	0.094 (2)	0.0741 (18)	0.136 (3)	−0.0151 (16)	0.059 (2)	−0.0216 (17)
C15	0.082 (4)	0.139 (6)	0.149 (5)	−0.045 (4)	0.060 (4)	−0.051 (5)
C16	0.142 (6)	0.163 (7)	0.107 (4)	0.039 (5)	0.029 (4)	0.018 (4)
C15'	0.142 (9)	0.174 (10)	0.181 (9)	−0.029 (8)	0.065 (8)	0.033 (8)
C16'	0.098 (6)	0.193 (9)	0.156 (7)	0.000 (6)	0.037 (5)	0.007 (7)
C17	0.183 (6)	0.123 (5)	0.118 (4)	0.041 (4)	0.001 (4)	0.004 (4)
C18	0.155 (6)	0.110 (4)	0.094 (4)	0.021 (4)	0.042 (4)	−0.005 (3)
C17'	0.151 (8)	0.157 (9)	0.107 (7)	0.029 (7)	0.042 (6)	0.029 (7)
C18'	0.095 (6)	0.121 (8)	0.083 (6)	0.002 (6)	0.030 (5)	0.000 (6)
N1	0.0602 (10)	0.0416 (9)	0.0541 (9)	−0.0036 (7)	0.0120 (8)	−0.0030 (7)
N2	0.0621 (10)	0.0441 (10)	0.0661 (11)	−0.0044 (8)	0.0110 (8)	−0.0015 (8)
N3	0.0744 (12)	0.0507 (10)	0.0860 (13)	−0.0094 (9)	0.0339 (10)	−0.0097 (9)
O1	0.0978 (13)	0.0648 (11)	0.0927 (12)	−0.0184 (9)	0.0484 (11)	−0.0170 (9)
O2	0.0882 (11)	0.0563 (10)	0.0750 (10)	−0.0013 (8)	0.0233 (9)	−0.0165 (8)
O3	0.1105 (15)	0.0799 (12)	0.0767 (12)	−0.0173 (10)	0.0123 (11)	0.0047 (9)

Geometric parameters (Å, º) top

C1—C3ⁱ	1.373 (3)	C14—H14B	0.9700
C1—C2	1.376 (3)	C14—H14C	0.9700
C1—H1	0.9300	C14—H14D	0.9700
C2—C3	1.376 (3)	C15—C16	1.494 (8)
C2—N1	1.444 (2)	C15—H15A	0.9700
C3—C1ⁱ	1.373 (3)	C15—H15B	0.9700
C3—H3	0.9300	C16—H16A	0.9600
C4—N2	1.314 (3)	C16—H16B	0.9600
C4—N3	1.340 (3)	C16—H16C	0.9600
C4—N1	1.396 (3)	C15'—C16'	1.484 (9)
C5—N2	1.356 (3)	C15'—H15C	0.9700
C5—C6	1.359 (3)	C15'—H15D	0.9700
C5—C8	1.451 (3)	C16'—H16D	0.9600
C6—O2	1.380 (2)	C16'—H16E	0.9600
C6—C7	1.406 (3)	C16'—H16F	0.9600
C7—O1	1.221 (3)	C17—C18	1.439 (7)
C7—N1	1.412 (3)	C17—H17A	0.9600
C8—C9	1.387 (4)	C17—H17B	0.9600
C8—C13	1.391 (3)	C17—H17C	0.9600
C9—O2	1.378 (3)	C18—O3	1.415 (6)
C9—C10	1.379 (3)	C18—H18A	0.9700
C10—C11	1.372 (4)	C18—H18B	0.9700
C10—H10	0.9300	C17'—C18'	1.482 (9)
C11—C12	1.386 (4)	C17'—H17D	0.9600
C11—H11	0.9300	C17'—H17E	0.9600
C12—C13	1.375 (4)	C17'—H17F	0.9600
C12—H12	0.9300	C18'—O3	1.457 (8)
C13—H13	0.9300	C18'—H18C	0.9700
C14—C15	1.442 (6)	C18'—H18D	0.9700
C14—N3	1.446 (3)	N3—H3A	0.8600
C14—C15'	1.561 (9)	O3—H3B	0.8200
C14—H14A	0.9700

C3ⁱ—C1—C2	119.50 (18)	N3—C14—H14D	111.9
C3ⁱ—C1—H1	120.3	C15'—C14—H14D	112.0
C2—C1—H1	120.3	H14A—C14—H14D	17.5
C3—C2—C1	120.85 (18)	H14B—C14—H14D	89.3
C3—C2—N1	119.49 (17)	H14C—C14—H14D	109.6
C1—C2—N1	119.65 (17)	C14—C15—C16	108.0 (6)
C1ⁱ—C3—C2	119.65 (18)	C14—C15—H15A	110.1
C1ⁱ—C3—H3	120.2	C16—C15—H15A	110.1
C2—C3—H3	120.2	C14—C15—H15B	110.1
N2—C4—N3	120.22 (19)	C16—C15—H15B	110.1
N2—C4—N1	122.93 (19)	H15A—C15—H15B	108.4
N3—C4—N1	116.85 (18)	C16'—C15'—C14	113.9 (9)
N2—C5—C6	125.20 (19)	C16'—C15'—H15C	108.8
N2—C5—C8	129.4 (2)	C14—C15'—H15C	108.8
C6—C5—C8	105.39 (19)	C16'—C15'—H15D	108.8
C5—C6—O2	113.20 (18)	C14—C15'—H15D	108.8
C5—C6—C7	122.9 (2)	H15C—C15'—H15D	107.7
O2—C6—C7	123.9 (2)	C15'—C16'—H16D	109.5
O1—C7—C6	128.7 (2)	C15'—C16'—H16E	109.5
O1—C7—N1	121.00 (19)	H16D—C16'—H16E	109.5
C6—C7—N1	110.25 (19)	C15'—C16'—H16F	109.5
C9—C8—C13	119.0 (2)	H16D—C16'—H16F	109.5
C9—C8—C5	105.22 (19)	H16E—C16'—H16F	109.5
C13—C8—C5	135.7 (2)	O3—C18—C17	110.6 (5)
O2—C9—C10	124.5 (3)	O3—C18—H18A	109.5
O2—C9—C8	111.97 (18)	C17—C18—H18A	109.5
C10—C9—C8	123.5 (2)	O3—C18—H18B	109.5
C11—C10—C9	116.3 (3)	C17—C18—H18B	109.5
C11—C10—H10	121.8	H18A—C18—H18B	108.1
C9—C10—H10	121.8	C18'—C17'—H17D	109.5
C10—C11—C12	121.5 (2)	C18'—C17'—H17E	109.5
C10—C11—H11	119.3	H17D—C17'—H17E	109.5
C12—C11—H11	119.3	C18'—C17'—H17F	109.5
C13—C12—C11	121.7 (3)	H17D—C17'—H17F	109.5
C13—C12—H12	119.2	H17E—C17'—H17F	109.5
C11—C12—H12	119.2	O3—C18'—C17'	109.3 (9)
C12—C13—C8	117.9 (3)	O3—C18'—H18C	109.8
C12—C13—H13	121.0	C17'—C18'—H18C	109.8
C8—C13—H13	121.0	O3—C18'—H18D	109.8
C15—C14—N3	121.6 (4)	C17'—C18'—H18D	109.8
C15—C14—C15'	30.8 (5)	H18C—C18'—H18D	108.3
N3—C14—C15'	99.0 (5)	C4—N1—C7	124.16 (18)
C15—C14—H14A	106.9	C4—N1—C2	120.16 (16)
N3—C14—H14A	106.9	C7—N1—C2	115.68 (16)
C15'—C14—H14A	97.2	C4—N2—C5	114.54 (18)
C15—C14—H14B	106.9	C4—N3—C14	122.8 (2)
N3—C14—H14B	106.9	C4—N3—H3A	118.6
C15'—C14—H14B	137.2	C14—N3—H3A	118.6
H14A—C14—H14B	106.7	C9—O2—C6	104.22 (18)
C15—C14—H14C	83.4	C18—O3—C18'	31.7 (4)
N3—C14—H14C	111.9	C18—O3—H3A	124.5
C15'—C14—H14C	112.2	C18'—O3—H3A	102.6
H14A—C14—H14C	125.7	C18—O3—H3B	109.5
H14B—C14—H14C	26.1	C18'—O3—H3B	110.8
C15—C14—H14D	114.7	H3A—O3—H3B	119.4

C3ⁱ—C1—C2—C3	0.2 (3)	N3—C14—C15'—C16'	179.6 (12)
C3ⁱ—C1—C2—N1	178.92 (18)	N2—C4—N1—C7	2.6 (3)
C1—C2—C3—C1ⁱ	−0.2 (4)	N3—C4—N1—C7	−176.89 (18)
N1—C2—C3—C1ⁱ	−178.92 (18)	N2—C4—N1—C2	−177.97 (18)
N2—C5—C6—O2	−178.42 (17)	N3—C4—N1—C2	2.6 (3)
C8—C5—C6—O2	0.5 (2)	O1—C7—N1—C4	179.69 (19)
N2—C5—C6—C7	0.2 (3)	C6—C7—N1—C4	−0.5 (3)
C8—C5—C6—C7	179.07 (19)	O1—C7—N1—C2	0.2 (3)
C5—C6—C7—O1	179.0 (2)	C6—C7—N1—C2	180.00 (17)
O2—C6—C7—O1	−2.5 (4)	C3—C2—N1—C4	−101.3 (2)
C5—C6—C7—N1	−0.7 (3)	C1—C2—N1—C4	80.0 (2)
O2—C6—C7—N1	177.70 (18)	C3—C2—N1—C7	78.2 (2)
N2—C5—C8—C9	178.42 (19)	C1—C2—N1—C7	−100.5 (2)
C6—C5—C8—C9	−0.4 (2)	N3—C4—N2—C5	176.47 (18)
N2—C5—C8—C13	−0.4 (4)	N1—C4—N2—C5	−3.0 (3)
C6—C5—C8—C13	−179.3 (2)	C6—C5—N2—C4	1.7 (3)
C13—C8—C9—O2	179.31 (18)	C8—C5—N2—C4	−176.91 (18)
C5—C8—C9—O2	0.2 (2)	N2—C4—N3—C14	0.8 (3)
C13—C8—C9—C10	−1.3 (3)	N1—C4—N3—C14	−179.7 (2)
C5—C8—C9—C10	179.6 (2)	C15—C14—N3—C4	81.6 (4)
O2—C9—C10—C11	179.4 (2)	C15'—C14—N3—C4	104.2 (8)
C8—C9—C10—C11	0.1 (3)	C10—C9—O2—C6	−179.3 (2)
C9—C10—C11—C12	0.7 (4)	C8—C9—O2—C6	0.0 (2)
C10—C11—C12—C13	−0.2 (4)	C5—C6—O2—C9	−0.3 (2)
C11—C12—C13—C8	−0.9 (3)	C7—C6—O2—C9	−178.9 (2)
C9—C8—C13—C12	1.6 (3)	C17—C18—O3—C18'	44.0 (11)
C5—C8—C13—C12	−179.6 (2)	C17—C18—O3—H3A	−8.6
N3—C14—C15—C16	68.1 (6)	C17'—C18'—O3—C18	−29.5 (10)
C15'—C14—C15—C16	20.3 (14)	C17'—C18'—O3—H3A	108.4
C15—C14—C15'—C16'	−40.1 (9)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3a···O3	0.86	2.22	2.996 (3)	150
O3—H3b···O1ⁱ	0.82	2.12	2.903 (3)	159

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₈N₆O₄·2C₂H₆O
M_r	652.74
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.1933 (12), 13.6224 (16), 12.5249 (15)
β (°)	105.409 (2)
V (Å³)	1676.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.988, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10883, 2941, 2327
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.151, 1.03
No. of reflections	2941
No. of parameters	259
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

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—H3a···O3	0.86	2.22	2.996 (3)	150
O3—H3b···O1ⁱ	0.82	2.12	2.903 (3)	159

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors are grateful to Dr X. G. Meng (Key Laboratory of Pesticides & Chemical Biology of the Ministry of Education, Central China Normal University, Wuhan, Hubei, China) for the data collection and analysis. This work was supported by the Natural Science Foundation of Hubei Provincial Department of Science and Technology (No. 2011CDB08301) and the Science Research Project of Hubei University of Medicine (Nos. 2011CXX03 and No. 2009QDJ15).

References

Bellarosa, D., Antonelli, G., Bambacioni, F., Giannotti, D., Viti, G., Nannicini, R., Giachetti, A., Dianzani, F., Witvrouw, M., Pauwels, R., Desmyter, J. & De Clercq, E. (1996). Antiviral Res. 30, 109–124. CrossRef CAS PubMed Web of Science Google Scholar
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., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y.-G., Zhu, Z.-R. & Chen, Y.-L. (2008). Acta Cryst. E64, o321–o322. Web of Science CSD CrossRef IUCr Journals 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1282-o1283

doi:10.1107/S160053681201375X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

3,3′-(1,4-Phenyl­ene)bis­­[2-(propyl­amino)­benzofuro[3,2-d]pyrimidin-4(3H)-one] ethanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3′-(1,4-Phenylene)bis[2-(propylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one] ethanol disolvate