Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026815/at2310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026815/at2310Isup2.hkl |
CCDC reference: 655601
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).
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).
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).
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.
Fig. 1. Perspective view of the title compound with the atom numbering. Displacement ellipsoids are at the 50% probability level. |
C15H10ClNO3 | F(000) = 592 |
Mr = 287.69 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7582 reflections |
a = 7.3643 (10) Å | θ = 3.5–25.7° |
b = 12.8295 (11) Å | µ = 0.30 mm−1 |
c = 13.9452 (14) Å | T = 173 K |
β = 93.898 (9)° | Block, brown |
V = 1314.5 (2) Å3 | 0.43 × 0.40 × 0.37 mm |
Z = 4 |
STOE IPDS II two-circle diffractometer | 2433 independent reflections |
Radiation source: fine-focus sealed tube | 1977 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −7→8 |
Tmin = 0.883, Tmax = 0.898 | k = −13→15 |
7978 measured reflections | l = −16→16 |
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)] = 0.041 | H-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 reflections | Δρmax = 0.26 e Å−3 |
182 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (2) |
C15H10ClNO3 | V = 1314.5 (2) Å3 |
Mr = 287.69 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.3643 (10) Å | µ = 0.30 mm−1 |
b = 12.8295 (11) Å | T = 173 K |
c = 13.9452 (14) Å | 0.43 × 0.40 × 0.37 mm |
β = 93.898 (9)° |
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 = 0.898 | Rint = 0.055 |
7978 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
2433 reflections | Δρmin = −0.28 e Å−3 |
182 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.20045 (8) | 0.15573 (4) | 0.60287 (3) | 0.03658 (19) | |
N1 | 0.5177 (2) | 0.91050 (12) | 0.71148 (11) | 0.0321 (4) | |
O1 | 0.3613 (3) | 0.52709 (11) | 0.68321 (10) | 0.0594 (6) | |
O2 | 0.5581 (2) | 1.00014 (10) | 0.68882 (11) | 0.0470 (4) | |
O3 | 0.5469 (2) | 0.87440 (12) | 0.79277 (9) | 0.0418 (4) | |
C1 | 0.3232 (3) | 0.55836 (14) | 0.60200 (13) | 0.0303 (5) | |
C2 | 0.2583 (3) | 0.48688 (15) | 0.52359 (13) | 0.0314 (5) | |
H2 | 0.2269 | 0.5149 | 0.4616 | 0.038* | |
C3 | 0.2423 (3) | 0.38477 (14) | 0.53709 (12) | 0.0275 (4) | |
H3 | 0.2738 | 0.3591 | 0.5999 | 0.033* | |
C11 | 0.3414 (3) | 0.67301 (13) | 0.58022 (12) | 0.0245 (4) | |
C12 | 0.4164 (3) | 0.73743 (14) | 0.65350 (12) | 0.0253 (4) | |
H12 | 0.4546 | 0.7093 | 0.7146 | 0.030* | |
C13 | 0.4339 (3) | 0.84219 (13) | 0.63547 (12) | 0.0247 (4) | |
C14 | 0.3776 (3) | 0.88744 (15) | 0.54758 (13) | 0.0288 (4) | |
H14 | 0.3895 | 0.9603 | 0.5377 | 0.035* | |
C15 | 0.3042 (3) | 0.82363 (15) | 0.47535 (13) | 0.0299 (4) | |
H15 | 0.2652 | 0.8526 | 0.4147 | 0.036* | |
C16 | 0.2868 (3) | 0.71654 (14) | 0.49089 (12) | 0.0276 (4) | |
H16 | 0.2377 | 0.6730 | 0.4404 | 0.033* | |
C21 | 0.1804 (3) | 0.30800 (14) | 0.46390 (12) | 0.0244 (4) | |
C22 | 0.1591 (3) | 0.20200 (14) | 0.48547 (12) | 0.0261 (4) | |
C23 | 0.0989 (3) | 0.12985 (15) | 0.41637 (14) | 0.0326 (5) | |
H23 | 0.0856 | 0.0587 | 0.4333 | 0.039* | |
C24 | 0.0579 (3) | 0.16236 (16) | 0.32188 (14) | 0.0356 (5) | |
H24 | 0.0165 | 0.1134 | 0.2741 | 0.043* | |
C25 | 0.0778 (3) | 0.26644 (16) | 0.29803 (14) | 0.0349 (5) | |
H25 | 0.0495 | 0.2890 | 0.2339 | 0.042* | |
C26 | 0.1392 (3) | 0.33786 (14) | 0.36791 (13) | 0.0305 (4) | |
H26 | 0.1537 | 0.4088 | 0.3503 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0563 (4) | 0.0228 (3) | 0.0303 (3) | 0.0022 (2) | 0.0010 (2) | 0.00355 (17) |
N1 | 0.0376 (11) | 0.0251 (8) | 0.0332 (9) | −0.0014 (8) | −0.0014 (7) | −0.0066 (7) |
O1 | 0.1133 (16) | 0.0240 (8) | 0.0363 (8) | −0.0050 (9) | −0.0284 (9) | 0.0049 (6) |
O2 | 0.0688 (12) | 0.0213 (8) | 0.0491 (9) | −0.0094 (8) | −0.0087 (8) | −0.0055 (6) |
O3 | 0.0591 (11) | 0.0380 (8) | 0.0269 (7) | −0.0061 (8) | −0.0064 (6) | −0.0040 (6) |
C1 | 0.0378 (12) | 0.0213 (9) | 0.0306 (10) | −0.0005 (8) | −0.0053 (8) | 0.0002 (7) |
C2 | 0.0416 (13) | 0.0222 (9) | 0.0297 (10) | −0.0025 (9) | −0.0034 (8) | 0.0006 (7) |
C3 | 0.0321 (11) | 0.0231 (9) | 0.0266 (9) | 0.0005 (8) | −0.0026 (7) | 0.0004 (7) |
C11 | 0.0257 (10) | 0.0211 (9) | 0.0263 (9) | −0.0003 (8) | −0.0003 (7) | −0.0018 (7) |
C12 | 0.0279 (10) | 0.0243 (9) | 0.0236 (9) | 0.0016 (8) | 0.0002 (7) | −0.0001 (7) |
C13 | 0.0269 (10) | 0.0226 (9) | 0.0245 (9) | −0.0018 (8) | 0.0018 (7) | −0.0043 (7) |
C14 | 0.0331 (11) | 0.0217 (9) | 0.0317 (9) | −0.0003 (8) | 0.0033 (8) | 0.0018 (7) |
C15 | 0.0359 (11) | 0.0275 (10) | 0.0257 (9) | 0.0011 (8) | −0.0032 (8) | 0.0030 (7) |
C16 | 0.0320 (11) | 0.0249 (10) | 0.0251 (9) | −0.0008 (8) | −0.0029 (8) | −0.0032 (7) |
C21 | 0.0230 (10) | 0.0229 (9) | 0.0270 (9) | −0.0008 (7) | 0.0006 (7) | −0.0007 (7) |
C22 | 0.0268 (10) | 0.0240 (9) | 0.0274 (9) | 0.0008 (8) | 0.0021 (7) | −0.0011 (7) |
C23 | 0.0356 (12) | 0.0235 (9) | 0.0392 (11) | −0.0049 (9) | 0.0058 (8) | −0.0041 (8) |
C24 | 0.0348 (12) | 0.0356 (11) | 0.0359 (11) | −0.0054 (9) | −0.0023 (8) | −0.0119 (8) |
C25 | 0.0397 (12) | 0.0368 (11) | 0.0273 (9) | −0.0003 (10) | −0.0048 (8) | −0.0008 (8) |
C26 | 0.0348 (11) | 0.0256 (9) | 0.0306 (10) | −0.0019 (9) | −0.0012 (8) | 0.0004 (7) |
Cl1—C22 | 1.7486 (18) | C14—C15 | 1.380 (3) |
N1—O3 | 1.230 (2) | C14—H14 | 0.9500 |
N1—O2 | 1.234 (2) | C15—C16 | 1.398 (3) |
N1—C13 | 1.478 (2) | C15—H15 | 0.9500 |
O1—C1 | 1.216 (2) | C16—H16 | 0.9500 |
C1—C2 | 1.481 (2) | C21—C22 | 1.404 (3) |
C1—C11 | 1.510 (2) | C21—C26 | 1.406 (2) |
C2—C3 | 1.330 (3) | C22—C23 | 1.387 (3) |
C2—H2 | 0.9500 | C23—C24 | 1.395 (3) |
C3—C21 | 1.468 (2) | C23—H23 | 0.9500 |
C3—H3 | 0.9500 | C24—C25 | 1.386 (3) |
C11—C12 | 1.399 (2) | C24—H24 | 0.9500 |
C11—C16 | 1.399 (2) | C25—C26 | 1.391 (3) |
C12—C13 | 1.375 (3) | C25—H25 | 0.9500 |
C12—H12 | 0.9500 | C26—H26 | 0.9500 |
C13—C14 | 1.394 (2) | ||
O3—N1—O2 | 123.84 (16) | C14—C15—C16 | 120.36 (16) |
O3—N1—C13 | 118.42 (15) | C14—C15—H15 | 119.8 |
O2—N1—C13 | 117.71 (15) | C16—C15—H15 | 119.8 |
O1—C1—C2 | 121.70 (17) | C15—C16—C11 | 120.44 (16) |
O1—C1—C11 | 119.39 (16) | C15—C16—H16 | 119.8 |
C2—C1—C11 | 118.90 (15) | C11—C16—H16 | 119.8 |
C3—C2—C1 | 122.19 (17) | C22—C21—C26 | 116.61 (16) |
C3—C2—H2 | 118.9 | C22—C21—C3 | 122.33 (16) |
C1—C2—H2 | 118.9 | C26—C21—C3 | 121.06 (17) |
C2—C3—C21 | 126.06 (17) | C23—C22—C21 | 122.20 (17) |
C2—C3—H3 | 117.0 | C23—C22—Cl1 | 116.80 (14) |
C21—C3—H3 | 117.0 | C21—C22—Cl1 | 120.96 (13) |
C12—C11—C16 | 119.34 (16) | C22—C23—C24 | 119.66 (18) |
C12—C11—C1 | 117.70 (15) | C22—C23—H23 | 120.2 |
C16—C11—C1 | 122.96 (15) | C24—C23—H23 | 120.2 |
C13—C12—C11 | 118.77 (16) | C25—C24—C23 | 119.66 (17) |
C13—C12—H12 | 120.6 | C25—C24—H24 | 120.2 |
C11—C12—H12 | 120.6 | C23—C24—H24 | 120.2 |
C12—C13—C14 | 122.83 (16) | C24—C25—C26 | 120.08 (18) |
C12—C13—N1 | 119.22 (16) | C24—C25—H25 | 120.0 |
C14—C13—N1 | 117.94 (15) | C26—C25—H25 | 120.0 |
C15—C14—C13 | 118.25 (17) | C25—C26—C21 | 121.78 (18) |
C15—C14—H14 | 120.9 | C25—C26—H26 | 119.1 |
C13—C14—H14 | 120.9 | C21—C26—H26 | 119.1 |
O1—C1—C2—C3 | −1.7 (3) | C13—C14—C15—C16 | 0.2 (3) |
C11—C1—C2—C3 | 178.7 (2) | C14—C15—C16—C11 | 0.9 (3) |
C1—C2—C3—C21 | −179.60 (19) | C12—C11—C16—C15 | −1.1 (3) |
O1—C1—C11—C12 | 5.3 (3) | C1—C11—C16—C15 | 178.94 (19) |
C2—C1—C11—C12 | −175.09 (18) | C2—C3—C21—C22 | −176.8 (2) |
O1—C1—C11—C16 | −174.8 (2) | C2—C3—C21—C26 | 3.1 (3) |
C2—C1—C11—C16 | 4.9 (3) | C26—C21—C22—C23 | −0.6 (3) |
C16—C11—C12—C13 | 0.2 (3) | C3—C21—C22—C23 | 179.33 (18) |
C1—C11—C12—C13 | −179.82 (18) | C26—C21—C22—Cl1 | −178.37 (14) |
C11—C12—C13—C14 | 0.9 (3) | C3—C21—C22—Cl1 | 1.6 (3) |
C11—C12—C13—N1 | −178.30 (17) | C21—C22—C23—C24 | 0.1 (3) |
O3—N1—C13—C12 | −9.7 (3) | Cl1—C22—C23—C24 | 178.00 (16) |
O2—N1—C13—C12 | 168.70 (19) | C22—C23—C24—C25 | 0.0 (3) |
O3—N1—C13—C14 | 171.00 (18) | C23—C24—C25—C26 | 0.3 (3) |
O2—N1—C13—C14 | −10.5 (3) | C24—C25—C26—C21 | −0.8 (3) |
C12—C13—C14—C15 | −1.1 (3) | C22—C21—C26—C25 | 0.9 (3) |
N1—C13—C14—C15 | 178.10 (17) | C3—C21—C26—C25 | −179.01 (19) |
Experimental details
Crystal data | |
Chemical formula | C15H10ClNO3 |
Mr | 287.69 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 7.3643 (10), 12.8295 (11), 13.9452 (14) |
β (°) | 93.898 (9) |
V (Å3) | 1314.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.43 × 0.40 × 0.37 |
Data collection | |
Diffractometer | STOE IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.883, 0.898 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7978, 2433, 1977 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.608 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.112, 1.04 |
No. of reflections | 2433 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.28 |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
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.