Literature DB >> 22412620

2,4-Dichloro-7-fluoro-quinazoline.

Abstract

The mol-ecule of the title compound, C(8)H(3)Cl(2)FN(2), is essentially planar, with a maximum deviation of 0.018 (2) Å. In the crystal, π-π stacking is observed between parallel quinazoline moieties of adjacent mol-ecules, the centroid-centroid distance being 3.8476 (14) Å.

Entities: Chemical Disease Gene Species

Year: 2012 PMID： 22412620 PMCID： PMC3295509 DOI： 10.1107/S1600536812006125

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

Related literature

For the synthesis of quinazoline derivatives, see: Roberts et al. (2011 ▶); Gao et al. (2010 ▶); Li et al. (2009 ▶); Connolly et al. (2005 ▶). For the pharmacological properties of quinazoline analogues, see: Koller et al. (2011 ▶); Garofalo et al. (2011 ▶); Yang et al. (2011 ▶). For related structures, see: Jia et al. (2011 ▶); Ouahrouch et al. (2011 ▶).

Experimental

Crystal data

C8H3Cl2FN2 M = 217.02 Monoclinic, a = 3.8257 (3) Å b = 15.0664 (9) Å c = 14.3453 (6) Å β = 95.102 (5)° V = 823.59 (9) Å3 Z = 4 Mo Kα radiation μ = 0.75 mm−1 T = 293 K 0.35 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.780, T max = 0.835 3156 measured reflections 1452 independent reflections 1120 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.095 S = 1.07 1452 reflections 118 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.23 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006125/xu5446sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006125/xu5446Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812006125/xu5446Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₈H₃Cl₂FN₂	F(000) = 432
M_r = 217.02	D_x = 1.750 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.8257 (3) Å	Cell parameters from 1033 reflections
b = 15.0664 (9) Å	θ = 3.0–25.0°
c = 14.3453 (6) Å	µ = 0.75 mm⁻¹
β = 95.102 (5)°	T = 293 K
V = 823.59 (9) Å³	Block, brown
Z = 4	0.35 × 0.30 × 0.25 mm

Agilent Xcalibur Eos diffractometer	1452 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −15→17
T_min = 0.780, T_max = 0.835	l = −16→16
3156 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0389P)²] where P = (F_o² + 2F_c²)/3
1452 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Cl1	0.18763 (19)	0.24582 (4)	0.86579 (4)	0.0500 (3)
Cl2	0.2734 (2)	0.09054 (5)	0.54819 (5)	0.0628 (3)
F1	0.8584 (4)	0.55046 (10)	0.60324 (11)	0.0652 (5)
N1	0.2491 (5)	0.17987 (14)	0.70176 (14)	0.0416 (5)
N2	0.4812 (5)	0.25290 (13)	0.57255 (14)	0.0389 (5)
C1	0.3448 (6)	0.18701 (17)	0.61375 (17)	0.0392 (6)
C2	0.3050 (6)	0.25134 (16)	0.75263 (17)	0.0360 (6)
C3	0.4494 (6)	0.33043 (16)	0.72000 (16)	0.0331 (6)
C4	0.5323 (6)	0.32793 (16)	0.62626 (16)	0.0327 (6)
C5	0.6758 (7)	0.40354 (16)	0.58670 (16)	0.0389 (6)
H5	0.7365	0.4030	0.5253	0.047*
C6	0.7228 (7)	0.47677 (17)	0.64004 (19)	0.0428 (7)
C7	0.6403 (7)	0.48233 (17)	0.73259 (19)	0.0455 (7)
H7	0.6783	0.5346	0.7665	0.055*
C8	0.5030 (7)	0.40973 (16)	0.77230 (17)	0.0426 (7)
H8	0.4443	0.4122	0.8338	0.051*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0595 (5)	0.0612 (5)	0.0313 (4)	0.0047 (4)	0.0158 (3)	0.0092 (3)
Cl2	0.0870 (6)	0.0476 (5)	0.0541 (5)	−0.0111 (4)	0.0086 (4)	−0.0150 (4)
F1	0.0783 (13)	0.0466 (10)	0.0717 (12)	−0.0159 (9)	0.0123 (10)	0.0132 (9)
N1	0.0454 (14)	0.0428 (13)	0.0367 (12)	−0.0035 (11)	0.0043 (10)	0.0014 (11)
N2	0.0455 (13)	0.0404 (13)	0.0314 (11)	−0.0004 (11)	0.0074 (10)	−0.0032 (10)
C1	0.0433 (16)	0.0373 (15)	0.0369 (14)	0.0015 (13)	0.0029 (12)	−0.0033 (12)
C2	0.0330 (14)	0.0469 (16)	0.0285 (12)	0.0071 (12)	0.0045 (11)	0.0052 (12)
C3	0.0320 (14)	0.0385 (14)	0.0286 (12)	0.0057 (12)	0.0022 (11)	0.0039 (11)
C4	0.0301 (14)	0.0365 (14)	0.0315 (13)	0.0033 (12)	0.0019 (11)	0.0037 (11)
C5	0.0427 (16)	0.0437 (16)	0.0311 (13)	0.0022 (13)	0.0074 (12)	0.0037 (12)
C6	0.0389 (15)	0.0397 (16)	0.0493 (16)	−0.0033 (13)	0.0008 (13)	0.0123 (14)
C7	0.0504 (17)	0.0370 (15)	0.0485 (16)	0.0004 (13)	0.0013 (13)	−0.0069 (13)
C8	0.0469 (17)	0.0478 (16)	0.0336 (14)	0.0060 (14)	0.0066 (12)	−0.0037 (13)

Cl1—C2	1.724 (2)	C3—C8	1.416 (3)
Cl2—C1	1.739 (3)	C4—C5	1.406 (3)
F1—C6	1.352 (3)	C5—C6	1.346 (3)
N1—C2	1.308 (3)	C5—H5	0.9300
N1—C1	1.350 (3)	C6—C7	1.394 (4)
N2—C1	1.289 (3)	C7—C8	1.360 (3)
N2—C4	1.372 (3)	C7—H7	0.9300
C2—C3	1.411 (3)	C8—H8	0.9300
C3—C4	1.409 (3)

C2—N1—C1	114.3 (2)	C5—C4—C3	119.5 (2)
C1—N2—C4	114.9 (2)	C6—C5—C4	118.2 (2)
N2—C1—N1	130.1 (2)	C6—C5—H5	120.9
N2—C1—Cl2	116.50 (18)	C4—C5—H5	120.9
N1—C1—Cl2	113.36 (19)	C5—C6—F1	119.2 (2)
N1—C2—C3	124.0 (2)	C5—C6—C7	124.1 (2)
N1—C2—Cl1	116.25 (18)	F1—C6—C7	116.7 (2)
C3—C2—Cl1	119.70 (18)	C8—C7—C6	118.6 (2)
C4—C3—C2	115.0 (2)	C8—C7—H7	120.7
C4—C3—C8	119.6 (2)	C6—C7—H7	120.7
C2—C3—C8	125.4 (2)	C7—C8—C3	120.0 (2)
N2—C4—C5	118.8 (2)	C7—C8—H8	120.0
N2—C4—C3	121.7 (2)	C3—C8—H8	120.0

7 in total

1. Virtual screening and synthesis of quinazolines as novel JAK2 inhibitors.

Authors: Su Hui Yang; Daulat Bikram Khadka; Suk Hee Cho; Hye-Kyung Ju; Kwang Youl Lee; Ho Jae Han; Kyung-Tae Lee; Won-Jea Cho
Journal: Bioorg Med Chem Date: 2010-11-30 Impact factor: 3.641

2. A short history of SHELX.

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

3. Quinazolinedione sulfonamides: a novel class of competitive AMPA receptor antagonists with oral activity.

Authors: Manuel Koller; Kurt Lingenhoehl; Markus Schmutz; Ivan-Toma Vranesic; Joerg Kallen; Yves P Auberson; David A Carcache; Henri Mattes; Silvio Ofner; David Orain; Stephan Urwyler
Journal: Bioorg Med Chem Lett Date: 2011-04-08 Impact factor: 2.823

1 in total

1. Crystal structure of 4-meth-oxy-quinazoline.

Authors: Gamal A El-Hiti; Keith Smith; Amany S Hegazy; Mohammed B Alshammari; Benson M Kariuki
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2014-11-21