Literature DB >> 21589107

(2E)-1-(3-Bromo-phen-yl)-3-(4,5-dimeth-oxy-2-nitro-phen-yl)prop-2-en-1-one.

Jerry P Jasinski, Ray J Butcher, C S Chidan Kumar, H S Yathirajan, A N Mayekar.

Abstract

In the title compound, C(17)H(14)BrNO(5), the dihedral angle between the 3-bromo-substituted benzene ring and the 4,5-dimeth-oxy-2-nitro-phenyl ring is 15.2 (1)°. The dihedral angles between the mean plane of the propenone group and the mean planes of the 3-bromo-substituted benzene and 4,5-dimeth-oxy-2-nitro-phenyl rings are 6.9 (6) and 20.5 (5)°, respectively. Weak inter-molecular C-H⋯O inter-actions contribute to crystal stability and π-π inter-actions [centroid-centroid distances = 3.7072 (18) and 3.6326 (18) Å] are also observed.

Entities: Chemical Disease Gene

Year: 2010 PMID： 21589107 PMCID： PMC3009291 DOI： 10.1107/S1600536810041292

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

Related literature

For the biological activity of chalcones, see: Liu et al. (2003 ▶); Nielson et al. (1998 ▶); Rajas et al. (2002 ▶); Dinkova-Kostova et al. (1998 ▶). For their non-linear optical properties, see: Goto et al. (1991 ▶); Uchida et al. (1998 ▶);Tam et al. (1989 ▶); Indira et al. (2002 ▶); Sarojini et al. (2006 ▶). For the effect of bulky substituents on the spontaneous polarization of non-centrosymmetric crystals, see: Fichou et al. (1988 ▶). For the influence of the steric effect of the substituent on the molecular hyperpolarizability, see: Cho et al. (1996 ▶). For related structures, see: Butcher et al. (2007a ▶,b ▶,c ▶); Jasinski et al. (2010a ▶,b ▶,c ▶,d ▶,e ▶); Dutkiewicz et al. (2010 ▶); Kant et al. (2009 ▶); Yathirajan et al. (2007 ▶).

Experimental

Crystal data

C17H14BrNO5 M = 392.20 Orthorhombic, a = 6.8547 (2) Å b = 8.3205 (2) Å c = 27.1509 (6) Å V = 1548.54 (7) Å3 Z = 4 Cu Kα radiation μ = 3.88 mm−1 T = 123 K 0.55 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Diffractometer with Ruby Gemini detector Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.490, T max = 1.000 9914 measured reflections 3069 independent reflections 3011 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.086 S = 1.07 3069 reflections 219 parameters H-atom parameters constrained Δρmax = 0.74 e Å−3 Δρmin = −0.42 e Å−3 Absolute structure: Flack (1983 ▶), 1228 Friedel pairs Flack parameter: 0.08 (2) Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810041292/lx2178sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041292/lx2178Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₄BrNO₅	F(000) = 792
M_r = 392.20	D_x = 1.682 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8339 reflections
a = 6.8547 (2) Å	θ = 4.9–74.0°
b = 8.3205 (2) Å	µ = 3.88 mm⁻¹
c = 27.1509 (6) Å	T = 123 K
V = 1548.54 (7) Å³	Needle, colorless
Z = 4	0.55 × 0.12 × 0.06 mm

Oxford Diffraction Xcalibur Diffractometer with Ruby Gemini detector	3069 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3011 reflections with I > 2σ(I)
graphite	R_int = 0.040
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 5.6°
ω scans	h = −8→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→10
T_min = 0.490, T_max = 1.000	l = −32→33
9914 measured reflections

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0497P)² + 1.5041P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.003
3069 reflections	Δρ_max = 0.74 e Å⁻³
219 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1228 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (2)

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
Br	0.59396 (5)	0.54840 (4)	0.757218 (10)	0.02935 (11)
O1	0.5372 (4)	0.1224 (3)	0.60992 (8)	0.0329 (6)
O2	0.7701 (4)	−0.1958 (3)	0.50347 (8)	0.0314 (5)
O3	0.6537 (4)	−0.3581 (3)	0.44871 (9)	0.0332 (6)
O4	0.5820 (4)	0.0031 (2)	0.30190 (7)	0.0240 (4)
O5	0.5346 (4)	0.2869 (3)	0.33757 (7)	0.0258 (5)
N1	0.6855 (4)	−0.2223 (3)	0.46423 (10)	0.0227 (5)
C1	0.5862 (5)	0.4042 (3)	0.61065 (10)	0.0200 (5)
C2	0.5815 (5)	0.4043 (3)	0.66260 (10)	0.0227 (6)
H2A	0.5685	0.3064	0.6803	0.027*
C3	0.5960 (4)	0.5491 (4)	0.68724 (9)	0.0229 (5)
C4	0.6120 (5)	0.6943 (4)	0.66260 (11)	0.0247 (6)
H4A	0.6189	0.7925	0.6804	0.030*
C5	0.6179 (5)	0.6939 (4)	0.61128 (11)	0.0246 (6)
H5A	0.6296	0.7925	0.5938	0.030*
C6	0.6065 (4)	0.5491 (4)	0.58544 (10)	0.0230 (5)
H6A	0.6126	0.5494	0.5505	0.028*
C7	0.5701 (5)	0.2433 (4)	0.58575 (11)	0.0233 (6)
C8	0.5993 (5)	0.2348 (4)	0.53138 (10)	0.0224 (6)
H8A	0.6323	0.3286	0.5132	0.027*
C9	0.5783 (5)	0.0934 (3)	0.50851 (10)	0.0213 (5)
H9A	0.5488	0.0027	0.5284	0.026*
C10	0.5971 (4)	0.0665 (3)	0.45512 (9)	0.0191 (5)
C11	0.6283 (4)	−0.0843 (3)	0.43402 (10)	0.0199 (6)
C12	0.6209 (4)	−0.1121 (3)	0.38335 (10)	0.0206 (6)
H12A	0.6378	−0.2178	0.3708	0.025*
C13	0.5890 (5)	0.0144 (3)	0.35161 (9)	0.0198 (5)
C14	0.5639 (5)	0.1705 (3)	0.37128 (10)	0.0208 (6)
C15	0.5659 (4)	0.1943 (3)	0.42198 (10)	0.0203 (6)
H15A	0.5457	0.2995	0.4346	0.024*
C16	0.5963 (5)	−0.1555 (4)	0.28128 (10)	0.0255 (6)
H16A	0.5866	−0.1490	0.2453	0.038*
H16B	0.4900	−0.2223	0.2941	0.038*
H16C	0.7219	−0.2032	0.2904	0.038*
C17	0.5316 (6)	0.4499 (4)	0.35512 (11)	0.0317 (7)
H17A	0.5242	0.5236	0.3270	0.048*
H17B	0.6509	0.4714	0.3739	0.048*
H17C	0.4177	0.4657	0.3764	0.048*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04312 (19)	0.03241 (16)	0.01252 (15)	0.00224 (15)	−0.00131 (12)	−0.00345 (11)
O1	0.0530 (16)	0.0300 (11)	0.0157 (10)	−0.0028 (11)	0.0034 (10)	−0.0018 (9)
O2	0.0428 (14)	0.0333 (12)	0.0180 (11)	0.0038 (11)	−0.0085 (10)	0.0032 (9)
O3	0.0540 (16)	0.0227 (11)	0.0228 (11)	0.0026 (10)	0.0012 (10)	0.0005 (9)
O4	0.0377 (12)	0.0219 (9)	0.0123 (8)	−0.0006 (9)	−0.0012 (9)	−0.0026 (7)
O5	0.0456 (14)	0.0191 (10)	0.0125 (9)	−0.0002 (9)	−0.0034 (9)	0.0008 (8)
N1	0.0303 (13)	0.0223 (12)	0.0154 (11)	0.0032 (10)	0.0026 (10)	0.0010 (10)
C1	0.0200 (13)	0.0264 (13)	0.0135 (12)	0.0000 (12)	−0.0016 (12)	−0.0037 (10)
C2	0.0286 (15)	0.0251 (13)	0.0145 (13)	0.0015 (13)	0.0007 (13)	−0.0009 (10)
C3	0.0288 (14)	0.0309 (14)	0.0089 (11)	0.0029 (16)	−0.0014 (11)	−0.0035 (11)
C4	0.0282 (16)	0.0251 (13)	0.0207 (14)	0.0019 (13)	0.0019 (14)	−0.0027 (11)
C5	0.0298 (16)	0.0241 (14)	0.0200 (14)	0.0004 (13)	−0.0003 (13)	0.0022 (11)
C6	0.0255 (14)	0.0285 (14)	0.0150 (12)	0.0026 (15)	−0.0007 (11)	−0.0004 (11)
C7	0.0263 (15)	0.0280 (14)	0.0158 (13)	0.0005 (13)	−0.0018 (12)	−0.0008 (11)
C8	0.0258 (14)	0.0269 (13)	0.0146 (13)	−0.0019 (14)	0.0013 (12)	0.0002 (11)
C9	0.0252 (14)	0.0243 (13)	0.0144 (12)	0.0000 (12)	0.0004 (12)	0.0002 (10)
C10	0.0207 (12)	0.0234 (13)	0.0133 (12)	−0.0023 (13)	0.0001 (11)	−0.0006 (10)
C11	0.0227 (15)	0.0214 (13)	0.0155 (13)	−0.0002 (11)	0.0002 (11)	0.0025 (10)
C12	0.0267 (16)	0.0199 (12)	0.0150 (13)	−0.0012 (12)	0.0015 (12)	−0.0037 (10)
C13	0.0250 (14)	0.0229 (13)	0.0115 (11)	−0.0017 (12)	0.0004 (11)	−0.0024 (10)
C14	0.0253 (15)	0.0213 (13)	0.0159 (13)	−0.0019 (12)	0.0010 (11)	0.0023 (11)
C15	0.0232 (15)	0.0213 (13)	0.0163 (13)	−0.0007 (11)	−0.0001 (11)	−0.0022 (10)
C16	0.0371 (16)	0.0259 (14)	0.0135 (12)	0.0011 (14)	−0.0005 (14)	−0.0053 (10)
C17	0.056 (2)	0.0186 (14)	0.0210 (14)	−0.0006 (15)	0.0011 (13)	0.0006 (13)

Br—C3	1.900 (3)	C7—C8	1.491 (4)
O1—C7	1.222 (4)	C8—C9	1.338 (4)
O2—N1	1.233 (4)	C8—H8A	0.9500
O3—N1	1.225 (4)	C9—C10	1.472 (4)
O4—C13	1.354 (3)	C9—H9A	0.9500
O4—C16	1.436 (3)	C10—C11	1.395 (4)
O5—C14	1.348 (4)	C10—C15	1.410 (4)
O5—C17	1.437 (4)	C11—C12	1.396 (4)
N1—C11	1.465 (4)	C12—C13	1.378 (4)
C1—C6	1.393 (4)	C12—H12A	0.9500
C1—C2	1.411 (4)	C13—C14	1.415 (4)
C1—C7	1.504 (4)	C14—C15	1.391 (4)
C2—C3	1.382 (4)	C15—H15A	0.9500
C2—H2A	0.9500	C16—H16A	0.9800
C3—C4	1.386 (4)	C16—H16B	0.9800
C4—C5	1.394 (4)	C16—H16C	0.9800
C4—H4A	0.9500	C17—H17A	0.9800
C5—C6	1.397 (4)	C17—H17B	0.9800
C5—H5A	0.9500	C17—H17C	0.9800
C6—H6A	0.9500

C13—O4—C16	116.8 (2)	C10—C9—H9A	117.2
C14—O5—C17	117.1 (2)	C11—C10—C15	116.1 (2)
O3—N1—O2	123.1 (3)	C11—C10—C9	123.7 (3)
O3—N1—C11	118.9 (3)	C15—C10—C9	120.0 (2)
O2—N1—C11	118.0 (2)	C10—C11—C12	123.3 (3)
C6—C1—C2	119.5 (2)	C10—C11—N1	121.1 (2)
C6—C1—C7	123.8 (2)	C12—C11—N1	115.5 (2)
C2—C1—C7	116.6 (2)	C13—C12—C11	119.7 (3)
C3—C2—C1	118.9 (3)	C13—C12—H12A	120.2
C3—C2—H2A	120.6	C11—C12—H12A	120.2
C1—C2—H2A	120.6	O4—C13—C12	125.1 (2)
C2—C3—C4	122.2 (2)	O4—C13—C14	115.9 (2)
C2—C3—Br	118.8 (2)	C12—C13—C14	119.0 (2)
C4—C3—Br	119.1 (2)	O5—C14—C15	124.8 (3)
C3—C4—C5	118.9 (3)	O5—C14—C13	114.9 (2)
C3—C4—H4A	120.6	C15—C14—C13	120.2 (3)
C5—C4—H4A	120.6	C14—C15—C10	121.7 (3)
C4—C5—C6	120.2 (3)	C14—C15—H15A	119.1
C4—C5—H5A	119.9	C10—C15—H15A	119.1
C6—C5—H5A	119.9	O4—C16—H16A	109.5
C1—C6—C5	120.4 (2)	O4—C16—H16B	109.5
C1—C6—H6A	119.8	H16A—C16—H16B	109.5
C5—C6—H6A	119.8	O4—C16—H16C	109.5
O1—C7—C8	121.2 (3)	H16A—C16—H16C	109.5
O1—C7—C1	120.3 (3)	H16B—C16—H16C	109.5
C8—C7—C1	118.5 (3)	O5—C17—H17A	109.5
C9—C8—C7	119.1 (3)	O5—C17—H17B	109.5
C9—C8—H8A	120.5	H17A—C17—H17B	109.5
C7—C8—H8A	120.5	O5—C17—H17C	109.5
C8—C9—C10	125.5 (3)	H17A—C17—H17C	109.5
C8—C9—H9A	117.2	H17B—C17—H17C	109.5

C6—C1—C2—C3	0.4 (5)	C9—C10—C11—N1	−13.0 (5)
C7—C1—C2—C3	179.9 (3)	O3—N1—C11—C10	157.6 (3)
C1—C2—C3—C4	1.0 (5)	O2—N1—C11—C10	−25.0 (4)
C1—C2—C3—Br	−178.9 (3)	O3—N1—C11—C12	−26.6 (4)
C2—C3—C4—C5	−1.4 (5)	O2—N1—C11—C12	150.9 (3)
Br—C3—C4—C5	178.6 (3)	C10—C11—C12—C13	2.7 (5)
C3—C4—C5—C6	0.4 (5)	N1—C11—C12—C13	−173.1 (3)
C2—C1—C6—C5	−1.4 (5)	C16—O4—C13—C12	4.4 (5)
C7—C1—C6—C5	179.1 (3)	C16—O4—C13—C14	−176.6 (3)
C4—C5—C6—C1	1.0 (5)	C11—C12—C13—O4	178.8 (3)
C6—C1—C7—O1	−174.2 (3)	C11—C12—C13—C14	−0.2 (5)
C2—C1—C7—O1	6.3 (5)	C17—O5—C14—C15	8.8 (5)
C6—C1—C7—C8	7.0 (5)	C17—O5—C14—C13	−172.7 (3)
C2—C1—C7—C8	−172.5 (3)	O4—C13—C14—O5	0.6 (4)
O1—C7—C8—C9	3.7 (5)	C12—C13—C14—O5	179.7 (3)
C1—C7—C8—C9	−177.6 (3)	O4—C13—C14—C15	179.1 (3)
C7—C8—C9—C10	178.3 (3)	C12—C13—C14—C15	−1.8 (5)
C8—C9—C10—C11	161.5 (3)	O5—C14—C15—C10	179.9 (3)
C8—C9—C10—C15	−24.4 (5)	C13—C14—C15—C10	1.5 (5)
C15—C10—C11—C12	−2.9 (4)	C11—C10—C15—C14	0.8 (4)
C9—C10—C11—C12	171.4 (3)	C9—C10—C15—C14	−173.8 (3)
C15—C10—C11—N1	172.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O5ⁱ	0.98	2.46	3.383 (3)	157
C17—H17B···O3ⁱⁱ	0.98	2.48	3.116 (4)	123

Cg···Cg	D···A
Cg1···Cg2ⁱ	3.7072 (18)
Cg1···Cg2ⁱⁱ	3.6326 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O5ⁱ	0.98	2.46	3.383 (3)	157
C17—H17B⋯O3ⁱⁱ	0.98	2.48	3.116 (4)	123

Symmetry codes: (i) ; (ii) .

12 in total

1. The synthesis and effect of fluorinated chalcone derivatives on nitric oxide production.

Authors: Javier Rojas; Miguel Payá; José N Dominguez; M Luisa Ferrándiz
Journal: Bioorg Med Chem Lett Date: 2002-08-05 Impact factor: 2.823

2. Structure-activity relationships of antileishmanial and antimalarial chalcones.

Authors: Mei Liu; Prapon Wilairat; Simon L Croft; Agnes Lay-Choo Tan; Mei-Lin Go
Journal: Bioorg Med Chem Date: 2003-07-03 Impact factor: 3.641

3. Antileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis.

Authors: S F Nielsen; S B Christensen; G Cruciani; A Kharazmi; T Liljefors
Journal: J Med Chem Date: 1998-11-19 Impact factor: 7.446

4. (2E)-1-(2-Bromo-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Authors: Jerry P Jasinski; Ray J Butcher; K Veena; B Narayana; H S Yathirajan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-06-16

5. (E)-3-(4-Bromo-phen-yl)-1-(3,4-dichloro-phen-yl)prop-2-en-1-one.

Authors: Rajni Kant; B Narayana; K Veena; H S Yathirajan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-03-25

6. (2E)-1-(4-Bromo-phen-yl)-3-(4-fluoro-phen-yl)prop-2-en-1-one.

Authors: Grzegorz Dutkiewicz; K Veena; B Narayana; H S Yathirajan; Maciej Kubicki
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-30

7. (2E)-3-(4-Bromo-phen-yl)-1-(3-chloro-phen-yl)prop-2-en-1-one.

Authors: Jerry P Jasinski; Ray J Butcher; B Narayana; K Veena; H S Yathirajan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-12-16

8. Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers.

Authors: A T Dinkova-Kostova; C Abeygunawardana; P Talalay
Journal: J Med Chem Date: 1998-12-17 Impact factor: 7.446