Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058011/bt2586sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058011/bt2586Isup2.hkl |
CCDC reference: 672943
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.086
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.905 Tmax scaled 0.905 Tmin scaled 0.817 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 32.42 From the CIF: _reflns_number_total 2120 Count of symmetry unique reflns 2284 Completeness (_total/calc) 92.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: Teh et al. (2006); Butcher, Jasinski et al. (2007); Butcher, Yathirajan et al. (2007); Yathirajan et al. (2007). For related literature, see: Dimmock et al. (1999); Go et al. (2005); Opletalova & Sedivy, (1999); Opletalova, (2000); Opletalova et al., (2003).
A mixture of acetophenone (1.2 g, 0.01 mol) and 2-chlorobenzaldehyde (1.3 g, 0.01 mol) was stirred well. Sodium hydroxide (4 ml, 5%) was added and the mixture was stirred for 6 hrs. The separated precipitate was washed, dried and recrystallized from ethyl alcohol. (m.p.:318 K). Analysis found: C: 74.10, H: 4.51%; C15H11ClO requires C: 74.23, H: 4.57%.
The H atoms were placed in their calculated positions and then refined using the riding model with C—H = 0.93 Å, and with Uiso(H) = 1.18–1.20Ueq(C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C15H11ClO | F(000) = 504 |
Mr = 242.69 | Dx = 1.323 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3012 reflections |
a = 19.0061 (7) Å | θ = 4.8–32.4° |
b = 5.0646 (3) Å | µ = 0.29 mm−1 |
c = 12.6534 (4) Å | T = 296 K |
V = 1217.99 (9) Å3 | Prism, colorless |
Z = 4 | 0.48 × 0.45 × 0.34 mm |
Oxford Diffraction Gemini R CCD diffractometer | 2120 independent reflections |
Radiation source: fine-focus sealed tube | 1286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.4°, θmin = 4.8° |
ϕ and ω scans | h = −27→27 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −7→7 |
Tmin = 0.903, Tmax = 1.000 | l = −18→17 |
7585 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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0482P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
2120 reflections | Δρmax = 0.20 e Å−3 |
154 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2120 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (7) |
C15H11ClO | V = 1217.99 (9) Å3 |
Mr = 242.69 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 19.0061 (7) Å | µ = 0.29 mm−1 |
b = 5.0646 (3) Å | T = 296 K |
c = 12.6534 (4) Å | 0.48 × 0.45 × 0.34 mm |
Oxford Diffraction Gemini R CCD diffractometer | 2120 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1286 reflections with I > 2σ(I) |
Tmin = 0.903, Tmax = 1.000 | Rint = 0.027 |
7585 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.087 | Δρmax = 0.20 e Å−3 |
S = 0.96 | Δρmin = −0.23 e Å−3 |
2120 reflections | Absolute structure: Flack (1983), 2120 Friedel pairs |
154 parameters | Absolute structure parameter: 0.02 (7) |
1 restraint |
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 | ||
Cl | 0.68430 (3) | 0.75899 (13) | 0.51978 (6) | 0.0616 (2) | |
O | 0.49895 (9) | 0.0827 (4) | 0.52181 (13) | 0.0684 (5) | |
C1 | 0.44116 (9) | −0.1047 (4) | 0.66737 (15) | 0.0334 (4) | |
C2 | 0.40315 (10) | −0.2764 (4) | 0.60322 (17) | 0.0388 (5) | |
H2A | 0.4094 | −0.2711 | 0.5304 | 0.047* | |
C3 | 0.35630 (10) | −0.4545 (4) | 0.64633 (18) | 0.0448 (5) | |
H3A | 0.3310 | −0.5676 | 0.6026 | 0.054* | |
C4 | 0.34697 (11) | −0.4646 (4) | 0.7546 (2) | 0.0498 (6) | |
H4A | 0.3158 | −0.5856 | 0.7839 | 0.060* | |
C5 | 0.38403 (12) | −0.2949 (4) | 0.81904 (18) | 0.0482 (5) | |
H5A | 0.3776 | −0.3007 | 0.8919 | 0.058* | |
C6 | 0.43057 (10) | −0.1169 (4) | 0.77580 (16) | 0.0410 (5) | |
H6A | 0.4553 | −0.0031 | 0.8199 | 0.049* | |
C7 | 0.49182 (9) | 0.0816 (4) | 0.61733 (15) | 0.0388 (5) | |
C8 | 0.53307 (11) | 0.2646 (4) | 0.68406 (16) | 0.0399 (5) | |
H8A | 0.5279 | 0.2545 | 0.7570 | 0.048* | |
C9 | 0.57618 (10) | 0.4390 (4) | 0.64553 (17) | 0.0422 (5) | |
H9A | 0.5806 | 0.4423 | 0.5723 | 0.051* | |
C10 | 0.61854 (9) | 0.6302 (4) | 0.70391 (15) | 0.0356 (4) | |
C11 | 0.66921 (10) | 0.7863 (4) | 0.65482 (17) | 0.0394 (5) | |
C12 | 0.70887 (10) | 0.9688 (4) | 0.70996 (18) | 0.0445 (5) | |
H12A | 0.7424 | 1.0700 | 0.6749 | 0.053* | |
C13 | 0.69862 (10) | 1.0003 (5) | 0.81699 (18) | 0.0471 (5) | |
H13A | 0.7252 | 1.1226 | 0.8545 | 0.057* | |
C14 | 0.64873 (11) | 0.8496 (5) | 0.86826 (17) | 0.0482 (5) | |
H14A | 0.6417 | 0.8703 | 0.9405 | 0.058* | |
C15 | 0.60925 (11) | 0.6678 (4) | 0.81245 (16) | 0.0422 (5) | |
H15A | 0.5757 | 0.5680 | 0.8480 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0590 (3) | 0.0823 (4) | 0.0435 (2) | −0.0241 (3) | 0.0095 (3) | −0.0010 (3) |
O | 0.0775 (10) | 0.0902 (14) | 0.0374 (7) | −0.0422 (10) | 0.0054 (9) | −0.0072 (10) |
C1 | 0.0303 (8) | 0.0295 (10) | 0.0404 (10) | 0.0045 (7) | −0.0038 (7) | 0.0000 (9) |
C2 | 0.0374 (10) | 0.0380 (11) | 0.0411 (10) | 0.0062 (8) | −0.0063 (8) | −0.0024 (9) |
C3 | 0.0395 (10) | 0.0374 (12) | 0.0574 (13) | −0.0016 (9) | −0.0087 (10) | −0.0063 (10) |
C4 | 0.0452 (11) | 0.0409 (12) | 0.0634 (15) | −0.0068 (10) | −0.0008 (11) | 0.0077 (12) |
C5 | 0.0526 (13) | 0.0512 (14) | 0.0409 (10) | −0.0068 (11) | −0.0004 (9) | 0.0084 (11) |
C6 | 0.0449 (10) | 0.0356 (10) | 0.0424 (10) | −0.0037 (9) | −0.0053 (9) | 0.0012 (10) |
C7 | 0.0340 (9) | 0.0401 (12) | 0.0422 (10) | 0.0007 (8) | −0.0015 (8) | 0.0004 (10) |
C8 | 0.0415 (10) | 0.0399 (12) | 0.0384 (10) | −0.0030 (9) | −0.0033 (8) | 0.0003 (10) |
C9 | 0.0424 (10) | 0.0487 (13) | 0.0355 (9) | −0.0066 (10) | 0.0025 (8) | −0.0022 (9) |
C10 | 0.0307 (9) | 0.0358 (10) | 0.0403 (10) | 0.0022 (8) | −0.0022 (8) | 0.0042 (10) |
C11 | 0.0331 (9) | 0.0445 (12) | 0.0406 (10) | 0.0026 (8) | 0.0004 (8) | 0.0019 (10) |
C12 | 0.0328 (9) | 0.0429 (12) | 0.0578 (13) | −0.0036 (9) | −0.0041 (10) | 0.0024 (11) |
C13 | 0.0415 (11) | 0.0409 (11) | 0.0590 (13) | 0.0028 (10) | −0.0127 (10) | −0.0068 (11) |
C14 | 0.0498 (12) | 0.0547 (13) | 0.0400 (11) | 0.0053 (11) | −0.0068 (10) | −0.0094 (11) |
C15 | 0.0415 (11) | 0.0438 (11) | 0.0415 (10) | −0.0014 (9) | 0.0020 (8) | 0.0038 (10) |
Cl—C11 | 1.738 (2) | C8—C9 | 1.300 (3) |
O—C7 | 1.216 (3) | C8—H8A | 0.9300 |
C1—C6 | 1.388 (3) | C9—C10 | 1.460 (3) |
C1—C2 | 1.392 (3) | C9—H9A | 0.9300 |
C1—C7 | 1.489 (3) | C10—C11 | 1.392 (3) |
C2—C3 | 1.380 (3) | C10—C15 | 1.398 (3) |
C2—H2A | 0.9300 | C11—C12 | 1.382 (3) |
C3—C4 | 1.382 (3) | C12—C13 | 1.377 (3) |
C3—H3A | 0.9300 | C12—H12A | 0.9300 |
C4—C5 | 1.378 (3) | C13—C14 | 1.379 (3) |
C4—H4A | 0.9300 | C13—H13A | 0.9300 |
C5—C6 | 1.376 (3) | C14—C15 | 1.382 (3) |
C5—H5A | 0.9300 | C14—H14A | 0.9300 |
C6—H6A | 0.9300 | C15—H15A | 0.9300 |
C7—C8 | 1.479 (3) | ||
C6—C1—C2 | 118.25 (19) | C7—C8—H8A | 118.5 |
C6—C1—C7 | 122.84 (18) | C8—C9—C10 | 127.5 (2) |
C2—C1—C7 | 118.91 (18) | C8—C9—H9A | 116.3 |
C3—C2—C1 | 120.9 (2) | C10—C9—H9A | 116.3 |
C3—C2—H2A | 119.6 | C11—C10—C15 | 116.64 (19) |
C1—C2—H2A | 119.6 | C11—C10—C9 | 122.17 (19) |
C2—C3—C4 | 119.9 (2) | C15—C10—C9 | 121.19 (18) |
C2—C3—H3A | 120.0 | C12—C11—C10 | 122.1 (2) |
C4—C3—H3A | 120.0 | C12—C11—Cl | 117.37 (16) |
C5—C4—C3 | 119.8 (2) | C10—C11—Cl | 120.50 (16) |
C5—C4—H4A | 120.1 | C13—C12—C11 | 119.8 (2) |
C3—C4—H4A | 120.1 | C13—C12—H12A | 120.1 |
C6—C5—C4 | 120.1 (2) | C11—C12—H12A | 120.1 |
C6—C5—H5A | 119.9 | C12—C13—C14 | 119.7 (2) |
C4—C5—H5A | 119.9 | C12—C13—H13A | 120.1 |
C5—C6—C1 | 121.0 (2) | C14—C13—H13A | 120.1 |
C5—C6—H6A | 119.5 | C13—C14—C15 | 120.1 (2) |
C1—C6—H6A | 119.5 | C13—C14—H14A | 119.9 |
O—C7—C8 | 120.35 (18) | C15—C14—H14A | 119.9 |
O—C7—C1 | 119.84 (18) | C14—C15—C10 | 121.6 (2) |
C8—C7—C1 | 119.80 (17) | C14—C15—H15A | 119.2 |
C9—C8—C7 | 123.09 (19) | C10—C15—H15A | 119.2 |
C9—C8—H8A | 118.5 | ||
C6—C1—C2—C3 | −0.1 (3) | C7—C8—C9—C10 | 179.18 (19) |
C7—C1—C2—C3 | 179.19 (17) | C8—C9—C10—C11 | 172.1 (2) |
C1—C2—C3—C4 | −0.3 (3) | C8—C9—C10—C15 | −8.8 (3) |
C2—C3—C4—C5 | 0.6 (3) | C15—C10—C11—C12 | 0.3 (3) |
C3—C4—C5—C6 | −0.4 (3) | C9—C10—C11—C12 | 179.46 (19) |
C4—C5—C6—C1 | −0.1 (3) | C15—C10—C11—Cl | −179.15 (15) |
C2—C1—C6—C5 | 0.3 (3) | C9—C10—C11—Cl | 0.0 (3) |
C7—C1—C6—C5 | −178.96 (18) | C10—C11—C12—C13 | −0.1 (3) |
C6—C1—C7—O | 179.8 (2) | Cl—C11—C12—C13 | 179.41 (16) |
C2—C1—C7—O | 0.5 (3) | C11—C12—C13—C14 | −0.1 (3) |
C6—C1—C7—C8 | −0.3 (3) | C12—C13—C14—C15 | 0.0 (3) |
C2—C1—C7—C8 | −179.62 (18) | C13—C14—C15—C10 | 0.3 (3) |
O—C7—C8—C9 | 2.5 (3) | C11—C10—C15—C14 | −0.4 (3) |
C1—C7—C8—C9 | −177.32 (19) | C9—C10—C15—C14 | −179.56 (19) |
Experimental details
Crystal data | |
Chemical formula | C15H11ClO |
Mr | 242.69 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 296 |
a, b, c (Å) | 19.0061 (7), 5.0646 (3), 12.6534 (4) |
V (Å3) | 1217.99 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.48 × 0.45 × 0.34 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.903, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7585, 2120, 1286 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.754 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.087, 0.96 |
No. of reflections | 2120 |
No. of parameters | 154 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.23 |
Absolute structure | Flack (1983), 2120 Friedel pairs |
Absolute structure parameter | 0.02 (7) |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
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Chalcone is a unique template molecule that is associated with several biological activities. Chalcone and its analogues are relatively easily available, not only by isolation from natural products but also by classical and combinatorial synthesis. The cytotoxic, anticancer, antiviral, antiprotozoal, insecticidal, chemopreventative, mutagenic and enzyme-inhibitory properties of a number of chalcones have been reviewed (Dimmock et al., 1999; Go et al., 2005). The antifungal and antibacterial activities of these compounds have also been reviewed (Opletalova & Sedivy, 1999; Opletalova, 2000). Chalcones and their analogues are also used as potential therapeutic agents in diseases of the cardiovascular system. The stabilizing action of chalcones on the vascular wall, vasodilating and antioxidative activity have been reported (Opletalova et al., 2003). The crystal structures of 1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Teh et al., 2006); 1-(2,4-dichlorophenyl)-3-[4-(methylsalfanyl)phenyl]prop-2-en-1-one (Butcher et al. 2007b); 1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one, (Yathirajan et al., 2007); 3-(4-chlorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one (Butcher et al. 2007a). As a part of our ongoing studies on chalcones, a new chalcone, C15H11ClO, was prepared and the crystal structure is reported.
In the title molecule, C15H11ClO, the angle between the mean planes of the 2-chlorophenyl-imino and phenol groups is 6.6 (8)° (Fig 1). Crystal packing is stabilized by van der Waals interactions, whereby the molecules are aligned in rows in a zigzag pattern with the phenyl rings diagonal to the ac face of the unit cell (Fig 2).