Literature DB >> 21581694

2,2'-Bis(4-fluoro-anilino)-3,3'-(3,6-dioxa-octane-1,8-di-yl)diquinazolin-4(3H)-one.

Xiang Wang, Zuan Ma, Yu-Lu Chen.   

Abstract

In the centrosymmetric title compound, C(34)H(30)F(2)N(6)O(4), the dihedral angle between the quinazolinone and fluorobenzene ring planes are 71.00 (2) and 74.94 (2)° and an intra-molecular N-H⋯O interaction stabilizes the conformation. In the crystal, C-H⋯F and C-H⋯O links help to establish the packing.

Entities:  

Year:  2008        PMID： 21581694      PMCID： PMC2967967          DOI： 10.1107/S1600536808040841

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 624.64 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.146 S = 1.06 2834 reflections 208 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.16 e Å−3 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040841/at2676sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040841/at2676Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C34H30F2N6O4F(000) = 1304
Mr = 624.64Dx = 1.282 Mg m−3
Monoclinic, C2/cMelting point: 415 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 13.923 (3) ÅCell parameters from 3566 reflections
b = 12.509 (3) Åθ = 2.2–28.5°
c = 18.726 (4) ŵ = 0.10 mm−1
β = 97.08 (3)°T = 295 K
V = 3236.6 (11) Å3Block, colourless
Z = 40.20 × 0.10 × 0.10 mm
Bruker SMART 4K CCD area-detector diffractometer2834 independent reflections
Radiation source: fine-focus sealed tube2263 reflections with I > 2σ(I)
graphiteRint = 0.012
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −16→16
Tmin = 0.982, Tmax = 0.991k = 0→14
2834 measured reflectionsl = 0→22
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.146w = 1/[σ2(Fo2) + (0.0807P)2 + 0.8957P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2834 reflectionsΔρmax = 0.30 e Å−3
208 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0028 (9)
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.
xyzUiso*/Ueq
C10.24654 (14)0.79492 (18)0.12370 (9)0.0755 (6)
C20.24527 (18)0.85820 (18)0.18204 (11)0.0885 (7)
H20.26390.92950.18080.106*
C30.21577 (17)0.81506 (16)0.24356 (10)0.0807 (6)
H30.21400.85750.28410.097*
C40.18901 (12)0.70941 (14)0.24493 (8)0.0605 (4)
C50.19174 (14)0.64790 (16)0.18485 (9)0.0705 (5)
H50.17400.57630.18580.085*
C60.22039 (15)0.69037 (18)0.12292 (9)0.0771 (6)
H60.22180.64870.08190.093*
C70.21556 (14)0.65123 (13)0.36984 (9)0.0621 (4)
C80.36454 (15)0.65449 (13)0.43630 (9)0.0675 (5)
C90.46390 (16)0.67547 (17)0.44028 (11)0.0822 (6)
H90.48930.70230.40030.099*
C100.52371 (19)0.65675 (19)0.50253 (12)0.0928 (7)
H100.58950.67130.50440.111*
C110.4878 (2)0.61653 (19)0.56277 (12)0.0948 (7)
H110.52920.60410.60480.114*
C120.3909 (2)0.59501 (16)0.56025 (10)0.0852 (6)
H120.36660.56820.60070.102*
C130.32810 (15)0.61330 (13)0.49687 (9)0.0680 (5)
C140.22605 (15)0.58965 (14)0.49317 (9)0.0704 (5)
C150.06541 (15)0.60240 (16)0.42379 (11)0.0761 (6)
H15A0.03500.65770.39240.091*
H15B0.04680.61410.47140.091*
C160.02768 (14)0.49650 (16)0.39706 (11)0.0774 (6)
H16A0.06500.43970.42250.093*
H16B−0.03930.48870.40550.093*
C17−0.00666 (15)0.39575 (15)0.28882 (13)0.0858 (6)
H17A−0.07510.39310.29390.103*
H17B0.02410.33310.31210.103*
F10.27593 (11)0.83760 (13)0.06324 (6)0.1146 (6)
N10.15482 (12)0.66559 (12)0.30729 (7)0.0698 (4)
H10.09490.64780.30560.084*
N20.17129 (11)0.61347 (11)0.42748 (7)0.0639 (4)
N70.30664 (12)0.67140 (12)0.37194 (7)0.0676 (4)
O10.18667 (12)0.55312 (13)0.54259 (7)0.0937 (5)
O20.03497 (9)0.48969 (9)0.32193 (7)0.0748 (4)
U11U22U33U12U13U23
C10.0723 (11)0.1035 (15)0.0487 (9)−0.0327 (10)−0.0003 (8)0.0192 (9)
C20.1115 (17)0.0794 (13)0.0736 (12)−0.0417 (12)0.0075 (11)0.0167 (10)
C30.1106 (16)0.0716 (12)0.0617 (10)−0.0257 (11)0.0181 (10)0.0020 (9)
C40.0631 (10)0.0661 (10)0.0522 (9)−0.0140 (8)0.0069 (7)0.0097 (7)
C50.0824 (12)0.0691 (11)0.0603 (10)−0.0180 (9)0.0098 (9)0.0049 (8)
C60.0859 (13)0.0933 (14)0.0526 (10)−0.0194 (11)0.0099 (9)0.0005 (9)
C70.0863 (12)0.0520 (9)0.0514 (9)−0.0073 (8)0.0223 (8)0.0021 (7)
C80.0941 (13)0.0543 (10)0.0550 (9)−0.0094 (9)0.0121 (9)−0.0040 (7)
C90.0958 (15)0.0788 (13)0.0710 (12)−0.0233 (11)0.0065 (11)−0.0028 (9)
C100.1032 (17)0.0882 (15)0.0835 (14)−0.0154 (12)−0.0025 (12)−0.0092 (11)
C110.118 (2)0.0860 (15)0.0751 (14)−0.0010 (14)−0.0111 (13)−0.0055 (11)
C120.128 (2)0.0717 (12)0.0567 (10)0.0069 (12)0.0138 (11)0.0024 (9)
C130.0973 (14)0.0537 (9)0.0548 (9)0.0057 (9)0.0162 (9)−0.0011 (7)
C140.1018 (15)0.0591 (10)0.0550 (9)0.0125 (9)0.0286 (9)0.0075 (8)
C150.0861 (13)0.0765 (12)0.0737 (11)0.0247 (10)0.0416 (10)0.0188 (9)
C160.0625 (11)0.0819 (13)0.0943 (13)0.0092 (9)0.0359 (10)0.0323 (10)
C170.0731 (12)0.0562 (10)0.1317 (18)−0.0043 (9)0.0273 (12)0.0129 (10)
F10.1282 (11)0.1552 (13)0.0596 (7)−0.0636 (9)0.0091 (7)0.0307 (7)
N10.0761 (10)0.0793 (10)0.0556 (8)−0.0195 (8)0.0152 (7)0.0120 (7)
N20.0824 (10)0.0582 (8)0.0561 (8)0.0061 (7)0.0290 (7)0.0089 (6)
N70.0820 (11)0.0696 (9)0.0527 (8)−0.0186 (8)0.0142 (7)0.0019 (6)
O10.1137 (11)0.1071 (11)0.0679 (8)0.0187 (9)0.0419 (8)0.0301 (8)
O20.0723 (8)0.0614 (7)0.0970 (10)−0.0068 (6)0.0353 (7)0.0114 (6)
C1—C21.351 (3)C10—H100.9300
C1—C61.357 (3)C11—C121.371 (3)
C1—F11.3597 (19)C11—H110.9300
C2—C31.380 (3)C12—C131.403 (3)
C2—H20.9300C12—H120.9300
C3—C41.374 (3)C13—C141.445 (3)
C3—H30.9300C14—O11.221 (2)
C4—C51.368 (2)C14—N21.397 (2)
C4—N11.4239 (19)C15—N21.474 (2)
C5—C61.379 (2)C15—C161.489 (3)
C5—H50.9300C15—H15A0.9700
C6—H60.9300C15—H15B0.9700
C7—N71.289 (2)C16—O21.426 (2)
C7—N11.369 (2)C16—H16A0.9700
C7—N21.390 (2)C16—H16B0.9700
C8—N71.381 (2)C17—O21.419 (2)
C8—C131.397 (2)C17—C17i1.488 (5)
C8—C91.401 (3)C17—H17A0.9700
C9—C101.367 (3)C17—H17B0.9700
C9—H90.9300N1—H10.8600
C10—C111.384 (3)
C2—C1—C6122.90 (16)C11—C12—H12119.8
C2—C1—F1118.59 (19)C13—C12—H12119.8
C6—C1—F1118.50 (19)C8—C13—C12119.8 (2)
C1—C2—C3118.74 (19)C8—C13—C14119.35 (17)
C1—C2—H2120.6C12—C13—C14120.89 (18)
C3—C2—H2120.6O1—C14—N2119.99 (19)
C4—C3—C2120.08 (19)O1—C14—C13124.83 (18)
C4—C3—H3120.0N2—C14—C13115.17 (15)
C2—C3—H3120.0N2—C15—C16114.13 (15)
C5—C4—C3119.38 (16)N2—C15—H15A108.7
C5—C4—N1120.27 (15)C16—C15—H15A108.7
C3—C4—N1120.29 (16)N2—C15—H15B108.7
C4—C5—C6121.04 (18)C16—C15—H15B108.7
C4—C5—H5119.5H15A—C15—H15B107.6
C6—C5—H5119.5O2—C16—C15108.66 (14)
C1—C6—C5117.86 (18)O2—C16—H16A110.0
C1—C6—H6121.1C15—C16—H16A110.0
C5—C6—H6121.1O2—C16—H16B110.0
N7—C7—N1120.14 (14)C15—C16—H16B110.0
N7—C7—N2124.86 (16)H16A—C16—H16B108.3
N1—C7—N2115.00 (16)O2—C17—C17i109.48 (13)
N7—C8—C13122.25 (18)O2—C17—H17A109.8
N7—C8—C9118.96 (17)C17i—C17—H17A109.8
C13—C8—C9118.75 (18)O2—C17—H17B109.8
C10—C9—C8120.5 (2)C17i—C17—H17B109.8
C10—C9—H9119.8H17A—C17—H17B108.2
C8—C9—H9119.8C7—N1—C4121.22 (15)
C9—C10—C11120.9 (2)C7—N1—H1119.4
C9—C10—H10119.5C4—N1—H1119.4
C11—C10—H10119.5C7—N2—C14120.67 (16)
C12—C11—C10119.8 (2)C7—N2—C15122.16 (15)
C12—C11—H11120.1C14—N2—C15117.09 (14)
C10—C11—H11120.1C7—N7—C8117.59 (15)
C11—C12—C13120.3 (2)C17—O2—C16113.94 (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—N2178.81 (16)
C1—C2—C3—C40.4 (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—C4176.50 (15)
C3—C4—C5—C6−0.4 (3)C5—C4—N1—C7113.3 (2)
N1—C4—C5—C6176.98 (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—C5179.32 (17)N1—C7—N2—C14176.34 (15)
C4—C5—C6—C10.5 (3)N7—C7—N2—C15173.61 (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—C110.2 (3)C13—C14—N2—C73.6 (2)
C9—C10—C11—C120.0 (4)O1—C14—N2—C155.8 (3)
C10—C11—C12—C130.2 (3)C13—C14—N2—C15−173.17 (15)
N7—C8—C13—C12178.24 (16)C16—C15—N2—C789.7 (2)
C9—C8—C13—C120.7 (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—C72.4 (3)
C11—C12—C13—C14179.17 (19)C9—C8—N7—C7179.87 (17)
C8—C13—C14—O1179.66 (17)C17i—C17—O2—C16−178.87 (17)
C12—C13—C14—O1−0.1 (3)C15—C16—O2—C17−174.79 (15)
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.182.7954 (19)128
C16—H16A···F1ii0.972.543.388 (2)146
C16—H16B···O1iii0.972.433.377 (2)164
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O20.862.182.7954 (19)128
C16—H16A⋯F1i0.972.543.388 (2)146
C16—H16B⋯O1ii0.972.433.377 (2)164

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis and antimicrobial activity of some bis-quinazoline derivatives.

Authors:  S A Shiba; A A el-Khamry; M E Shaban; K S Atia
Journal:  Pharmazie       Date:  1997-03       Impact factor: 1.267
  2 in total

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