2,2′-Bis(4-fluoro­anilino)-3,3′-(3,6-dioxa­octane-1,8-di­yl)diquinazolin-4(3H)-one

Wang, X.; Ma, Z.; Chen, Y.-L.

doi:10.1107/S1600536808040841

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o53

doi:10.1107/S1600536808040841

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2,2′-Bis(4-fluoroanilino)-3,3′-(3,6-dioxaoctane-1,8-diyl)diquinazolin-4(3H)-one

Xiang Wang,^a ^* Zuan Ma ^b and Yu-Lu Chen ^c

^aDepartment of Chemistry, Kaili College, Guizhou 556000, People's Republic of China, ^bDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^cDepartment of Chemistry, Xianning Vocational and Technical College, Xianning 437100, People's Republic of China
^*Correspondence e-mail: wangx0828@sina.com

(Received 10 November 2008; accepted 3 December 2008; online 10 December 2008)

In the centrosymmetric title compound, C₃₄H₃₀F₂N₆O₄, the dihedral angle between the quinazolinone and fluorobenzene ring planes are 71.00 (2) and 74.94 (2)° and an intramolecular N—H⋯O interaction stabilizes the conformation. In the crystal, C—H⋯F and C—H⋯O links help to establish the packing.

Related literature

For the biological activity of quinazolinones, see: Shiba et al. (1997 ); Ding et al., 2004 . For the crystal structures of other fused heterocyclic derivatives, see: Wang et al. (2006 ); Xu et al. (2006 ).

Experimental

Crystal data

C₃₄H₃₀F₂N₆O₄
M_r = 624.64
Monoclinic, C 2/c
a = 13.923 (3) Å
b = 12.509 (3) Å
c = 18.726 (4) Å
β = 97.08 (3)°
V = 3236.6 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.982, T_max = 0.991
2834 measured reflections
2834 independent reflections
2263 reflections with I > 2σ(I)
R_int = 0.0123

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.146
S = 1.06
2834 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.18	2.7954 (19)	128
C16—H16A⋯F1ⁱ	0.97	2.54	3.388 (2)	146
C16—H16B⋯O1ⁱⁱ	0.97	2.43	3.377 (2)	164
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -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, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040841/at2676sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040841/at2676Isup2.hkl

checkCIF report

Comment top

Quinazolinones are important heterocycles exhibiting good biological and pharmaceutical activities. Some of these actities inclue antimicrobial, anti-inflammatory, antifungal, anticancer and AMPA receptor antagonistical properties (Shiba et al., 1997 and Ding et al., 2004). In connection with our ongoing heterocyclic synthesis and drug discovery project (Wang et al., 2006; Xu et al., 2006), we obtained the title compound by employing aza-Wittig reaction of beta-ethoxycarbonyl iminophosphorane with p-Flurophenyl isocyanate and subsequent 2-(2-(2-aminoethoxy)ethoxy)ethanamine under mild conditions. Herein, we present X-ray crystallographic analysis of the title compound, which may be used as a new precursor for obtaining bioactive molecules.

The selected bond lengths and angles are given in parameter see Table 1. In the molecule of the title compound (Fig. 1), the fused rings of quinazolinones are planar, and the phenyl (C1—C6) and (C1a—C6a) rings are twisted with respect to the two quinazolinone ring systems, making dihedral angles of 71.00 (2)° and 74.94 (2)°, respectively. The molecular conformation is stabilized by intermolecular N—H···O and O—H···N hydrogen bonds. In the crystal packing, intramolecular N—H···O and O—H···N hydrogen bonds and intermolecular C—H···F and C—H···O hydrogen bonds (Fig.2, Table 2) link the molecules, helping to stabilize the crystal structure.

Related literature top

For the biological activity of quinazolinones, see: Shiba et al. (1997); Ding et al., 2004. For the crystal structures of other fused heterocyclic derivatives, see: Wang et al. (2006); Xu et al. (2006).

Experimental top

To a solution of iminophosphorane (1.28 g, 3.0 mmol) in anhydrous THF (10 mL) was added p-Fluorophenyl isocyanate (0.41 g, 3.0 mmol) under nitrogen at room temperature. After standing for 10 h at 273-278K, the solvent was removed under reduced pressure and ethyl sther/petroleum ether (1:2, 10ml) was added to precipitate triphenylphosphine oxide. After filtration the solvent was removed to give the carbodiimide, which were used directly without further purification. To the solution of carbodiimide prepared above was added a solution of 2-(2-(2-aminoethoxy)ethoxy)ethanamine (3 mmol) in THF (10 mL). The mixture was stirred for 10 h at room temperature, concentrated under reduced pressure and the recrystallized from a mixed solvent of methanol and dichloromethane (1:2 v/v) at room temperature to give the title compound.

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, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram for title compound, showing the hydrogen bonds stacking interactions.

2,2'-Bis(4-fluoroanilino)-3,3'-(3,6-dioxaoctane-1,8- diyl)diquinazolin-4(3H)-one top

Crystal data top

C₃₄H₃₀F₂N₆O₄	F(000) = 1304
M_r = 624.64	D_x = 1.282 Mg m⁻³
Monoclinic, C2/c	Melting point: 415 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.923 (3) Å	Cell parameters from 3566 reflections
b = 12.509 (3) Å	θ = 2.2–28.5°
c = 18.726 (4) Å	µ = 0.10 mm⁻¹
β = 97.08 (3)°	T = 295 K
V = 3236.6 (11) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2834 independent reflections
Radiation source: fine-focus sealed tube	2263 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
T_min = 0.982, T_max = 0.991	k = 0→14
2834 measured reflections	l = 0→22

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0807P)² + 0.8957P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2834 reflections	Δρ_max = 0.30 e Å⁻³
208 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (9)

Crystal data top

C₃₄H₃₀F₂N₆O₄	V = 3236.6 (11) Å³
M_r = 624.64	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.923 (3) Å	µ = 0.10 mm⁻¹
b = 12.509 (3) Å	T = 295 K
c = 18.726 (4) Å	0.20 × 0.10 × 0.10 mm
β = 97.08 (3)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2834 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2263 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.991	R_int = 0.012
2834 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2834 reflections	Δρ_min = −0.16 e Å⁻³
208 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
C1	0.24654 (14)	0.79492 (18)	0.12370 (9)	0.0755 (6)
C2	0.24527 (18)	0.85820 (18)	0.18204 (11)	0.0885 (7)
H2	0.2639	0.9295	0.1808	0.106*
C3	0.21577 (17)	0.81506 (16)	0.24356 (10)	0.0807 (6)
H3	0.2140	0.8575	0.2841	0.097*
C4	0.18901 (12)	0.70941 (14)	0.24493 (8)	0.0605 (4)
C5	0.19174 (14)	0.64790 (16)	0.18485 (9)	0.0705 (5)
H5	0.1740	0.5763	0.1858	0.085*
C6	0.22039 (15)	0.69037 (18)	0.12292 (9)	0.0771 (6)
H6	0.2218	0.6487	0.0819	0.093*
C7	0.21556 (14)	0.65123 (13)	0.36984 (9)	0.0621 (4)
C8	0.36454 (15)	0.65449 (13)	0.43630 (9)	0.0675 (5)
C9	0.46390 (16)	0.67547 (17)	0.44028 (11)	0.0822 (6)
H9	0.4893	0.7023	0.4003	0.099*
C10	0.52371 (19)	0.65675 (19)	0.50253 (12)	0.0928 (7)
H10	0.5895	0.6713	0.5044	0.111*
C11	0.4878 (2)	0.61653 (19)	0.56277 (12)	0.0948 (7)
H11	0.5292	0.6041	0.6048	0.114*
C12	0.3909 (2)	0.59501 (16)	0.56025 (10)	0.0852 (6)
H12	0.3666	0.5682	0.6007	0.102*
C13	0.32810 (15)	0.61330 (13)	0.49687 (9)	0.0680 (5)
C14	0.22605 (15)	0.58965 (14)	0.49317 (9)	0.0704 (5)
C15	0.06541 (15)	0.60240 (16)	0.42379 (11)	0.0761 (6)
H15A	0.0350	0.6577	0.3924	0.091*
H15B	0.0468	0.6141	0.4714	0.091*
C16	0.02768 (14)	0.49650 (16)	0.39706 (11)	0.0774 (6)
H16A	0.0650	0.4397	0.4225	0.093*
H16B	−0.0393	0.4887	0.4055	0.093*
C17	−0.00666 (15)	0.39575 (15)	0.28882 (13)	0.0858 (6)
H17A	−0.0751	0.3931	0.2939	0.103*
H17B	0.0241	0.3331	0.3121	0.103*
F1	0.27593 (11)	0.83760 (13)	0.06324 (6)	0.1146 (6)
N1	0.15482 (12)	0.66559 (12)	0.30729 (7)	0.0698 (4)
H1	0.0949	0.6478	0.3056	0.084*
N2	0.17129 (11)	0.61347 (11)	0.42748 (7)	0.0639 (4)
N7	0.30664 (12)	0.67140 (12)	0.37194 (7)	0.0676 (4)
O1	0.18667 (12)	0.55312 (13)	0.54259 (7)	0.0937 (5)
O2	0.03497 (9)	0.48969 (9)	0.32193 (7)	0.0748 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0723 (11)	0.1035 (15)	0.0487 (9)	−0.0327 (10)	−0.0003 (8)	0.0192 (9)
C2	0.1115 (17)	0.0794 (13)	0.0736 (12)	−0.0417 (12)	0.0075 (11)	0.0167 (10)
C3	0.1106 (16)	0.0716 (12)	0.0617 (10)	−0.0257 (11)	0.0181 (10)	0.0020 (9)
C4	0.0631 (10)	0.0661 (10)	0.0522 (9)	−0.0140 (8)	0.0069 (7)	0.0097 (7)
C5	0.0824 (12)	0.0691 (11)	0.0603 (10)	−0.0180 (9)	0.0098 (9)	0.0049 (8)
C6	0.0859 (13)	0.0933 (14)	0.0526 (10)	−0.0194 (11)	0.0099 (9)	0.0005 (9)
C7	0.0863 (12)	0.0520 (9)	0.0514 (9)	−0.0073 (8)	0.0223 (8)	0.0021 (7)
C8	0.0941 (13)	0.0543 (10)	0.0550 (9)	−0.0094 (9)	0.0121 (9)	−0.0040 (7)
C9	0.0958 (15)	0.0788 (13)	0.0710 (12)	−0.0233 (11)	0.0065 (11)	−0.0028 (9)
C10	0.1032 (17)	0.0882 (15)	0.0835 (14)	−0.0154 (12)	−0.0025 (12)	−0.0092 (11)
C11	0.118 (2)	0.0860 (15)	0.0751 (14)	−0.0010 (14)	−0.0111 (13)	−0.0055 (11)
C12	0.128 (2)	0.0717 (12)	0.0567 (10)	0.0069 (12)	0.0138 (11)	0.0024 (9)
C13	0.0973 (14)	0.0537 (9)	0.0548 (9)	0.0057 (9)	0.0162 (9)	−0.0011 (7)
C14	0.1018 (15)	0.0591 (10)	0.0550 (9)	0.0125 (9)	0.0286 (9)	0.0075 (8)
C15	0.0861 (13)	0.0765 (12)	0.0737 (11)	0.0247 (10)	0.0416 (10)	0.0188 (9)
C16	0.0625 (11)	0.0819 (13)	0.0943 (13)	0.0092 (9)	0.0359 (10)	0.0323 (10)
C17	0.0731 (12)	0.0562 (10)	0.1317 (18)	−0.0043 (9)	0.0273 (12)	0.0129 (10)
F1	0.1282 (11)	0.1552 (13)	0.0596 (7)	−0.0636 (9)	0.0091 (7)	0.0307 (7)
N1	0.0761 (10)	0.0793 (10)	0.0556 (8)	−0.0195 (8)	0.0152 (7)	0.0120 (7)
N2	0.0824 (10)	0.0582 (8)	0.0561 (8)	0.0061 (7)	0.0290 (7)	0.0089 (6)
N7	0.0820 (11)	0.0696 (9)	0.0527 (8)	−0.0186 (8)	0.0142 (7)	0.0019 (6)
O1	0.1137 (11)	0.1071 (11)	0.0679 (8)	0.0187 (9)	0.0419 (8)	0.0301 (8)
O2	0.0723 (8)	0.0614 (7)	0.0970 (10)	−0.0068 (6)	0.0353 (7)	0.0114 (6)

Geometric parameters (Å, º) top

C1—C2	1.351 (3)	C10—H10	0.9300
C1—C6	1.357 (3)	C11—C12	1.371 (3)
C1—F1	1.3597 (19)	C11—H11	0.9300
C2—C3	1.380 (3)	C12—C13	1.403 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.374 (3)	C13—C14	1.445 (3)
C3—H3	0.9300	C14—O1	1.221 (2)
C4—C5	1.368 (2)	C14—N2	1.397 (2)
C4—N1	1.4239 (19)	C15—N2	1.474 (2)
C5—C6	1.379 (2)	C15—C16	1.489 (3)
C5—H5	0.9300	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C7—N7	1.289 (2)	C16—O2	1.426 (2)
C7—N1	1.369 (2)	C16—H16A	0.9700
C7—N2	1.390 (2)	C16—H16B	0.9700
C8—N7	1.381 (2)	C17—O2	1.419 (2)
C8—C13	1.397 (2)	C17—C17ⁱ	1.488 (5)
C8—C9	1.401 (3)	C17—H17A	0.9700
C9—C10	1.367 (3)	C17—H17B	0.9700
C9—H9	0.9300	N1—H1	0.8600
C10—C11	1.384 (3)

C2—C1—C6	122.90 (16)	C11—C12—H12	119.8
C2—C1—F1	118.59 (19)	C13—C12—H12	119.8
C6—C1—F1	118.50 (19)	C8—C13—C12	119.8 (2)
C1—C2—C3	118.74 (19)	C8—C13—C14	119.35 (17)
C1—C2—H2	120.6	C12—C13—C14	120.89 (18)
C3—C2—H2	120.6	O1—C14—N2	119.99 (19)
C4—C3—C2	120.08 (19)	O1—C14—C13	124.83 (18)
C4—C3—H3	120.0	N2—C14—C13	115.17 (15)
C2—C3—H3	120.0	N2—C15—C16	114.13 (15)
C5—C4—C3	119.38 (16)	N2—C15—H15A	108.7
C5—C4—N1	120.27 (15)	C16—C15—H15A	108.7
C3—C4—N1	120.29 (16)	N2—C15—H15B	108.7
C4—C5—C6	121.04 (18)	C16—C15—H15B	108.7
C4—C5—H5	119.5	H15A—C15—H15B	107.6
C6—C5—H5	119.5	O2—C16—C15	108.66 (14)
C1—C6—C5	117.86 (18)	O2—C16—H16A	110.0
C1—C6—H6	121.1	C15—C16—H16A	110.0
C5—C6—H6	121.1	O2—C16—H16B	110.0
N7—C7—N1	120.14 (14)	C15—C16—H16B	110.0
N7—C7—N2	124.86 (16)	H16A—C16—H16B	108.3
N1—C7—N2	115.00 (16)	O2—C17—C17ⁱ	109.48 (13)
N7—C8—C13	122.25 (18)	O2—C17—H17A	109.8
N7—C8—C9	118.96 (17)	C17ⁱ—C17—H17A	109.8
C13—C8—C9	118.75 (18)	O2—C17—H17B	109.8
C10—C9—C8	120.5 (2)	C17ⁱ—C17—H17B	109.8
C10—C9—H9	119.8	H17A—C17—H17B	108.2
C8—C9—H9	119.8	C7—N1—C4	121.22 (15)
C9—C10—C11	120.9 (2)	C7—N1—H1	119.4
C9—C10—H10	119.5	C4—N1—H1	119.4
C11—C10—H10	119.5	C7—N2—C14	120.67 (16)
C12—C11—C10	119.8 (2)	C7—N2—C15	122.16 (15)
C12—C11—H11	120.1	C14—N2—C15	117.09 (14)
C10—C11—H11	120.1	C7—N7—C8	117.59 (15)
C11—C12—C13	120.3 (2)	C17—O2—C16	113.94 (14)

C6—C1—C2—C3	−0.3 (4)	C8—C13—C14—N2	−1.5 (2)
F1—C1—C2—C3	−179.8 (2)	C12—C13—C14—N2	178.81 (16)
C1—C2—C3—C4	0.4 (4)	N2—C15—C16—O2	−71.71 (19)
C2—C3—C4—C5	−0.1 (3)	N7—C7—N1—C4	−4.2 (3)
C2—C3—C4—N1	−177.47 (19)	N2—C7—N1—C4	176.50 (15)
C3—C4—C5—C6	−0.4 (3)	C5—C4—N1—C7	113.3 (2)
N1—C4—C5—C6	176.98 (17)	C3—C4—N1—C7	−69.4 (2)
C2—C1—C6—C5	−0.2 (3)	N7—C7—N2—C14	−2.9 (3)
F1—C1—C6—C5	179.32 (17)	N1—C7—N2—C14	176.34 (15)
C4—C5—C6—C1	0.5 (3)	N7—C7—N2—C15	173.61 (17)
N7—C8—C9—C10	−178.14 (18)	N1—C7—N2—C15	−7.1 (2)
C13—C8—C9—C10	−0.5 (3)	O1—C14—N2—C7	−177.52 (16)
C8—C9—C10—C11	0.2 (3)	C13—C14—N2—C7	3.6 (2)
C9—C10—C11—C12	0.0 (4)	O1—C14—N2—C15	5.8 (3)
C10—C11—C12—C13	0.2 (3)	C13—C14—N2—C15	−173.17 (15)
N7—C8—C13—C12	178.24 (16)	C16—C15—N2—C7	89.7 (2)
C9—C8—C13—C12	0.7 (3)	C16—C15—N2—C14	−93.65 (19)
N7—C8—C13—C14	−1.5 (3)	N1—C7—N7—C8	−179.41 (15)
C9—C8—C13—C14	−179.00 (17)	N2—C7—N7—C8	−0.2 (3)
C11—C12—C13—C8	−0.5 (3)	C13—C8—N7—C7	2.4 (3)
C11—C12—C13—C14	179.17 (19)	C9—C8—N7—C7	179.87 (17)
C8—C13—C14—O1	179.66 (17)	C17ⁱ—C17—O2—C16	−178.87 (17)
C12—C13—C14—O1	−0.1 (3)	C15—C16—O2—C17	−174.79 (15)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.18	2.7954 (19)	128
C16—H16A···F1ⁱⁱ	0.97	2.54	3.388 (2)	146
C16—H16B···O1ⁱⁱⁱ	0.97	2.43	3.377 (2)	164

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

Experimental details

Crystal data
Chemical formula	C₃₄H₃₀F₂N₆O₄
M_r	624.64
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	13.923 (3), 12.509 (3), 18.726 (4)
β (°)	97.08 (3)
V (Å³)	3236.6 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.982, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2834, 2834, 2263
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.06
No. of reflections	2834
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.16

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.18	2.7954 (19)	128.0
C16—H16A···F1ⁱ	0.97	2.54	3.388 (2)	145.8
C16—H16B···O1ⁱⁱ	0.97	2.43	3.377 (2)	164.1

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

Acknowledgements

We thank Dr Xiang-Gao Meng for the X-ray data collection.

References

Bruker (2001). SMART and SAINT-Plus . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, M. W., Chen, Y. F. & Huang, N. Y. (2004). Eur. J. Org. Chem. pp. 3872–3878. Web of Science CrossRef 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
Shiba, S. A., El-Khamry, A. A., Shaban, M. E. & Atia, K. S. (1997). Pharmazie, 52, 189–194. CAS PubMed Web of Science Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X., Zheng, A.-H. & Xu, S.-Z. (2006). Acta Cryst. E62, o4791–o4792. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, S.-Z., Hu, Y.-G., Wang, X. & Ding, M.-W. (2006). Acta Cryst. E62, o2229–o2230. Web of Science CSD CrossRef 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′-Bis(4-fluoro­anilino)-3,3′-(3,6-dioxa­octane-1,8-di­yl)diquinazolin-4(3H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-Bis(4-fluoroanilino)-3,3′-(3,6-dioxaoctane-1,8-diyl)diquinazolin-4(3H)-one