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Geometric parameters of the title compound, C15H10ClNO3, a chalcone derivative, are in the usual ranges. The mol­ecules are almost planar and crystallize in stacks with an interplanar distance of approximately 3.4 Å. No classical hydrogen bonds were found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026815/at2310sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026815/at2310Isup2.hkl
Contains datablock I

CCDC reference: 655601

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.041
  • wR factor = 0.112
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

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Comment top

Chalcones are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff have been recently subjects of great interest for their interesting pharmacological activities. Reviews on the bioactivities of varieties of chalcones are published in the literature recently. Recently, it has been noted that, among many organic compounds reported for their second harmonic generation, chalcone derivatives are known for their excellent blue light transmittance and good crystallizability. In continuation of our broad programme on chalcones, the present paper reports the crystal structure of a newly synthesized chalcone.

Geometric parameters of the title compound are in the usual ranges. The molecules are almost planar (r.m.s. deviation for all non-H atoms 0.113 Å) and crystallize in stacks. There is no classical hydrogen bonds.

Related literature top

For related structures, see: Yathirajan, Mayekar, Narayana et al. (2007); Fischer et al. (2007); Yathirajan, Mayekar, Sarojini et al. (2007).

For related literature, see: Di Carlo et al. (1999); Dimmock et al. (1999); Go et al. (2005); Fichou et al. (1988); Goto et al. (1991); Uchida et al. (1998); Sarojini et al. (2006).

Experimental top

To a thoroughly stirred solution of 1-(3-nitrophenyl)ethanone (1.65 g, 0.01 mol) and 2-chlorobenzaldehyde (1.40 g, 0.01 mol) in 25 ml me thanol, 5 ml of 30% KOH solution was added. The solution was stirred overnight and filtered. The product was crystallized from acetone by slow evaporation (m.p.: 410–412 K). Analysis for C15H10ClNO3: Found (Calculated): C 62.56 (62.62), H 3.41 (3.50), N 4.81 (4.87).

Refinement top

H atoms were found in a difference map, but they were refined using a riding model with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

Chalcones are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff have been recently subjects of great interest for their interesting pharmacological activities. Reviews on the bioactivities of varieties of chalcones are published in the literature recently. Recently, it has been noted that, among many organic compounds reported for their second harmonic generation, chalcone derivatives are known for their excellent blue light transmittance and good crystallizability. In continuation of our broad programme on chalcones, the present paper reports the crystal structure of a newly synthesized chalcone.

Geometric parameters of the title compound are in the usual ranges. The molecules are almost planar (r.m.s. deviation for all non-H atoms 0.113 Å) and crystallize in stacks. There is no classical hydrogen bonds.

For related structures, see: Yathirajan, Mayekar, Narayana et al. (2007); Fischer et al. (2007); Yathirajan, Mayekar, Sarojini et al. (2007).

For related literature, see: Di Carlo et al. (1999); Dimmock et al. (1999); Go et al. (2005); Fichou et al. (1988); Goto et al. (1991); Uchida et al. (1998); Sarojini et al. (2006).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering. Displacement ellipsoids are at the 50% probability level.
(2E)-3-(2-Chlorophenyl)-1-(3-nitrophenyl)prop-2-en-1-one top
Crystal data top
C15H10ClNO3F(000) = 592
Mr = 287.69Dx = 1.454 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7582 reflections
a = 7.3643 (10) Åθ = 3.5–25.7°
b = 12.8295 (11) ŵ = 0.30 mm1
c = 13.9452 (14) ÅT = 173 K
β = 93.898 (9)°Block, brown
V = 1314.5 (2) Å30.43 × 0.40 × 0.37 mm
Z = 4
Data collection top
STOE IPDS II two-circle
diffractometer
2433 independent reflections
Radiation source: fine-focus sealed tube1977 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 78
Tmin = 0.883, Tmax = 0.898k = 1315
7978 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1649P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2433 reflectionsΔρmax = 0.26 e Å3
182 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (2)
Crystal data top
C15H10ClNO3V = 1314.5 (2) Å3
Mr = 287.69Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.3643 (10) ŵ = 0.30 mm1
b = 12.8295 (11) ÅT = 173 K
c = 13.9452 (14) Å0.43 × 0.40 × 0.37 mm
β = 93.898 (9)°
Data collection top
STOE IPDS II two-circle
diffractometer
2433 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
1977 reflections with I > 2σ(I)
Tmin = 0.883, Tmax = 0.898Rint = 0.055
7978 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.04Δρmax = 0.26 e Å3
2433 reflectionsΔρmin = 0.28 e Å3
182 parameters
Special details top

Experimental. ;

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
xyzUiso*/Ueq
Cl10.20045 (8)0.15573 (4)0.60287 (3)0.03658 (19)
N10.5177 (2)0.91050 (12)0.71148 (11)0.0321 (4)
O10.3613 (3)0.52709 (11)0.68321 (10)0.0594 (6)
O20.5581 (2)1.00014 (10)0.68882 (11)0.0470 (4)
O30.5469 (2)0.87440 (12)0.79277 (9)0.0418 (4)
C10.3232 (3)0.55836 (14)0.60200 (13)0.0303 (5)
C20.2583 (3)0.48688 (15)0.52359 (13)0.0314 (5)
H20.22690.51490.46160.038*
C30.2423 (3)0.38477 (14)0.53709 (12)0.0275 (4)
H30.27380.35910.59990.033*
C110.3414 (3)0.67301 (13)0.58022 (12)0.0245 (4)
C120.4164 (3)0.73743 (14)0.65350 (12)0.0253 (4)
H120.45460.70930.71460.030*
C130.4339 (3)0.84219 (13)0.63547 (12)0.0247 (4)
C140.3776 (3)0.88744 (15)0.54758 (13)0.0288 (4)
H140.38950.96030.53770.035*
C150.3042 (3)0.82363 (15)0.47535 (13)0.0299 (4)
H150.26520.85260.41470.036*
C160.2868 (3)0.71654 (14)0.49089 (12)0.0276 (4)
H160.23770.67300.44040.033*
C210.1804 (3)0.30800 (14)0.46390 (12)0.0244 (4)
C220.1591 (3)0.20200 (14)0.48547 (12)0.0261 (4)
C230.0989 (3)0.12985 (15)0.41637 (14)0.0326 (5)
H230.08560.05870.43330.039*
C240.0579 (3)0.16236 (16)0.32188 (14)0.0356 (5)
H240.01650.11340.27410.043*
C250.0778 (3)0.26644 (16)0.29803 (14)0.0349 (5)
H250.04950.28900.23390.042*
C260.1392 (3)0.33786 (14)0.36791 (13)0.0305 (4)
H260.15370.40880.35030.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0563 (4)0.0228 (3)0.0303 (3)0.0022 (2)0.0010 (2)0.00355 (17)
N10.0376 (11)0.0251 (8)0.0332 (9)0.0014 (8)0.0014 (7)0.0066 (7)
O10.1133 (16)0.0240 (8)0.0363 (8)0.0050 (9)0.0284 (9)0.0049 (6)
O20.0688 (12)0.0213 (8)0.0491 (9)0.0094 (8)0.0087 (8)0.0055 (6)
O30.0591 (11)0.0380 (8)0.0269 (7)0.0061 (8)0.0064 (6)0.0040 (6)
C10.0378 (12)0.0213 (9)0.0306 (10)0.0005 (8)0.0053 (8)0.0002 (7)
C20.0416 (13)0.0222 (9)0.0297 (10)0.0025 (9)0.0034 (8)0.0006 (7)
C30.0321 (11)0.0231 (9)0.0266 (9)0.0005 (8)0.0026 (7)0.0004 (7)
C110.0257 (10)0.0211 (9)0.0263 (9)0.0003 (8)0.0003 (7)0.0018 (7)
C120.0279 (10)0.0243 (9)0.0236 (9)0.0016 (8)0.0002 (7)0.0001 (7)
C130.0269 (10)0.0226 (9)0.0245 (9)0.0018 (8)0.0018 (7)0.0043 (7)
C140.0331 (11)0.0217 (9)0.0317 (9)0.0003 (8)0.0033 (8)0.0018 (7)
C150.0359 (11)0.0275 (10)0.0257 (9)0.0011 (8)0.0032 (8)0.0030 (7)
C160.0320 (11)0.0249 (10)0.0251 (9)0.0008 (8)0.0029 (8)0.0032 (7)
C210.0230 (10)0.0229 (9)0.0270 (9)0.0008 (7)0.0006 (7)0.0007 (7)
C220.0268 (10)0.0240 (9)0.0274 (9)0.0008 (8)0.0021 (7)0.0011 (7)
C230.0356 (12)0.0235 (9)0.0392 (11)0.0049 (9)0.0058 (8)0.0041 (8)
C240.0348 (12)0.0356 (11)0.0359 (11)0.0054 (9)0.0023 (8)0.0119 (8)
C250.0397 (12)0.0368 (11)0.0273 (9)0.0003 (10)0.0048 (8)0.0008 (8)
C260.0348 (11)0.0256 (9)0.0306 (10)0.0019 (9)0.0012 (8)0.0004 (7)
Geometric parameters (Å, º) top
Cl1—C221.7486 (18)C14—C151.380 (3)
N1—O31.230 (2)C14—H140.9500
N1—O21.234 (2)C15—C161.398 (3)
N1—C131.478 (2)C15—H150.9500
O1—C11.216 (2)C16—H160.9500
C1—C21.481 (2)C21—C221.404 (3)
C1—C111.510 (2)C21—C261.406 (2)
C2—C31.330 (3)C22—C231.387 (3)
C2—H20.9500C23—C241.395 (3)
C3—C211.468 (2)C23—H230.9500
C3—H30.9500C24—C251.386 (3)
C11—C121.399 (2)C24—H240.9500
C11—C161.399 (2)C25—C261.391 (3)
C12—C131.375 (3)C25—H250.9500
C12—H120.9500C26—H260.9500
C13—C141.394 (2)
O3—N1—O2123.84 (16)C14—C15—C16120.36 (16)
O3—N1—C13118.42 (15)C14—C15—H15119.8
O2—N1—C13117.71 (15)C16—C15—H15119.8
O1—C1—C2121.70 (17)C15—C16—C11120.44 (16)
O1—C1—C11119.39 (16)C15—C16—H16119.8
C2—C1—C11118.90 (15)C11—C16—H16119.8
C3—C2—C1122.19 (17)C22—C21—C26116.61 (16)
C3—C2—H2118.9C22—C21—C3122.33 (16)
C1—C2—H2118.9C26—C21—C3121.06 (17)
C2—C3—C21126.06 (17)C23—C22—C21122.20 (17)
C2—C3—H3117.0C23—C22—Cl1116.80 (14)
C21—C3—H3117.0C21—C22—Cl1120.96 (13)
C12—C11—C16119.34 (16)C22—C23—C24119.66 (18)
C12—C11—C1117.70 (15)C22—C23—H23120.2
C16—C11—C1122.96 (15)C24—C23—H23120.2
C13—C12—C11118.77 (16)C25—C24—C23119.66 (17)
C13—C12—H12120.6C25—C24—H24120.2
C11—C12—H12120.6C23—C24—H24120.2
C12—C13—C14122.83 (16)C24—C25—C26120.08 (18)
C12—C13—N1119.22 (16)C24—C25—H25120.0
C14—C13—N1117.94 (15)C26—C25—H25120.0
C15—C14—C13118.25 (17)C25—C26—C21121.78 (18)
C15—C14—H14120.9C25—C26—H26119.1
C13—C14—H14120.9C21—C26—H26119.1
O1—C1—C2—C31.7 (3)C13—C14—C15—C160.2 (3)
C11—C1—C2—C3178.7 (2)C14—C15—C16—C110.9 (3)
C1—C2—C3—C21179.60 (19)C12—C11—C16—C151.1 (3)
O1—C1—C11—C125.3 (3)C1—C11—C16—C15178.94 (19)
C2—C1—C11—C12175.09 (18)C2—C3—C21—C22176.8 (2)
O1—C1—C11—C16174.8 (2)C2—C3—C21—C263.1 (3)
C2—C1—C11—C164.9 (3)C26—C21—C22—C230.6 (3)
C16—C11—C12—C130.2 (3)C3—C21—C22—C23179.33 (18)
C1—C11—C12—C13179.82 (18)C26—C21—C22—Cl1178.37 (14)
C11—C12—C13—C140.9 (3)C3—C21—C22—Cl11.6 (3)
C11—C12—C13—N1178.30 (17)C21—C22—C23—C240.1 (3)
O3—N1—C13—C129.7 (3)Cl1—C22—C23—C24178.00 (16)
O2—N1—C13—C12168.70 (19)C22—C23—C24—C250.0 (3)
O3—N1—C13—C14171.00 (18)C23—C24—C25—C260.3 (3)
O2—N1—C13—C1410.5 (3)C24—C25—C26—C210.8 (3)
C12—C13—C14—C151.1 (3)C22—C21—C26—C250.9 (3)
N1—C13—C14—C15178.10 (17)C3—C21—C26—C25179.01 (19)

Experimental details

Crystal data
Chemical formulaC15H10ClNO3
Mr287.69
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)7.3643 (10), 12.8295 (11), 13.9452 (14)
β (°) 93.898 (9)
V3)1314.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.43 × 0.40 × 0.37
Data collection
DiffractometerSTOE IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.883, 0.898
No. of measured, independent and
observed [I > 2σ(I)] reflections
7978, 2433, 1977
Rint0.055
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.112, 1.04
No. of reflections2433
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.28

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

 

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