Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037361/bx2102sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037361/bx2102Isup2.hkl |
CCDC reference: 660205
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.003 Å
- R factor = 0.052
- wR factor = 0.118
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For related background, see: Pati, Das, Ramirez-Erosa et al., (2007); Pati, Das, Sharma et al., (2007).
Desoxybenzoin (23.0 g, 0.102 mol) was dissolved in toluene (200 ml). In a separate 500 ml round-bottom flask equipped with a magnetic stirring bar, hydroxylamine hydrochloride (9.21 g, 0.132 mol) and potassium hydroxide (7.43 g, 0.132 mol) were suspended in absolute ethanol (50 ml) and stirred vigorously at room temperature for 30 min. The desoxybenzoin solution was added in one portion, and the yellow suspension was held at reflux, using a Dean-Stark trap to remove generated water, under a nitrogen blanket for 16 h. The suspension was cooled to room temperature and poured into water (200 ml). The system was extracted with ethyl acetate (2x150 ml), then the combined organic solution was washed with brine (200 ml), dried over sodium sulfate, and filtered. The solvents were evaporated under reduced pressure to yield a crude solid. The solid was recrystallized from hot ethanol and water, filtered and washed with water to yield, upon drying, desoxybenzoin keto-oxime (I) as white crystals (yield: 82%; m.p.: 389 K). IR(KBr): 3186, 2970, 2944, 1988, 1947, 1697, 1604, 1577, 1489, 1450, 1293, 1225, 1166, 1046, 965, 862, 721 cm-1; 1HNMR(CDCl3): 400Mz δ 3.77(s, 3H), 4.20(s, 2H), 6.87(m,1H), 7.16–7.26(m,8H); ESI(APCI)-MS: m/z 242(M+1).
All the H atoms were placed at geometrically expected positions with riding options. The distances with H atoms are Caromatic—H = 0.93 Å, Cmethylene—H = 0.97 Å, Cmethyl—H = 0.96 Å and O—H = 0.82 Å. The Uiso(H) was set to 1.2Ueq of parent atoms [1.5Ueq for methyl atom].
As a part of our interest in the design of candidate cytotoxins, based on the α, β-unsaturated keto scaffold, a series of compounds have been synthesized. These molecules have been shown to alkylate thiols but not amino or hydroxyl substituents; the latter two functional groups are found in nucleic acids suggesting that enones may be devoid of unwanted genetic mutations causing genotoxic properties, that is common among a number of anticancer drugs currently in use (Pati et al., 2007a) Pati et al., 2007b). The title molecule, C15H15NO2, (I), is one such compound, synthesized from structurally similar substituted desoxybenzoin precursor.
The three dimensional structure is composed of three planar subunits, namely, methoxyphenyl (O2/C1—C8), phenylethanone (C9—C15) and oxime (O1/N1/C1). The former two planes, on either side of oxime subunit make an angle of 87.9 (1)°, whereas the oxime subunit is oriented by 23.0 (2)° and 76.9 (1)° with respect to the first and second planes. Molecular structure is shown Fig. 1.
An intra-molecular C9B—H9B···O1 hydrogen bond stabilize the structure. O1 also participate in O1—H1···N1 hydrogen bond with another oxime subunit in the molecules related by (-x, 1 - y, 1 - z) (Table 1). The O—H···N hydrogen bonds cluster molecules into R22(6) dimers. There is a good Cg2···Cg2 stacking interaction, with the second Cg2 at (-x, 2 - y, 1 - z). The benzene rings are parallel to each other, 3.344 Å apart with a slippage of 4.107 Å. Cg2 is the centroid of the (C10—C15) ring. The center-to-center distance is 5.297 (2) Å. The intermolecular hydrogen bond and aromatic interactions interlink molecules into a one-dimensional array along b axis, as illustrated in Fig. 2. Two short contacts, i.e., C8—H8A..Cg1 [H···Cg = 2.74 Å, C—H···Cg = 138°] C8—H8C···Cg2 [H···Cg = 2.90 Å, C—H···Cg = 144°] were also observed in the crystal, where Cg1 (centroid of C2—C7 ring) and Cg2 are situated in the molecule at the symmetry position (1/2 + x, y, 1/2 - z). However, it is unlikely to have any structural significance, as methyl group is undergoing extremely rapid rotation about O2—C8.
For related background, see: Pati, Das, Ramirez-Erosa et al., (2007); Pati, Das, Sharma et al., (2007).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
C15H15NO2 | Dx = 1.264 Mg m−3 |
Mr = 241.28 | Melting point: 389 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1558 reflections |
a = 9.7198 (9) Å | θ = 2.8–17.9° |
b = 12.139 (1) Å | µ = 0.08 mm−1 |
c = 21.499 (2) Å | T = 295 K |
V = 2536.8 (4) Å3 | Cube, white |
Z = 8 | 0.22 × 0.16 × 0.10 mm |
F(000) = 1024 |
Bruker SMART CCD area-detector diffractometer | 2489 independent reflections |
Radiation source: fine-focus sealed tube | 1358 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ω and φ scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.901, Tmax = 0.982 | k = −14→14 |
18438 measured reflections | l = −26→25 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.4359P] where P = (Fo2 + 2Fc2)/3 |
2489 reflections | (Δ/σ)max < 0.001 |
165 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.11 e Å−3 |
C15H15NO2 | V = 2536.8 (4) Å3 |
Mr = 241.28 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.7198 (9) Å | µ = 0.08 mm−1 |
b = 12.139 (1) Å | T = 295 K |
c = 21.499 (2) Å | 0.22 × 0.16 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 2489 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1358 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.982 | Rint = 0.081 |
18438 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.16 e Å−3 |
2489 reflections | Δρmin = −0.11 e Å−3 |
165 parameters |
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. #===================================================================== Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = -0.71737(0.00029) m2 = 0.45861(0.00059) m3 = -0.52445(0.00048) D = -1.78586(0.00828) Atom d s d/s (d/s)**2 C1 * 0.0203 0.0022 9.396 88.292 C2 * 0.0014 0.0020 0.707 0.500 C3 * 0.0132 0.0023 5.852 34.248 C4 * -0.0039 0.0024 - 1.610 2.593 C5 * -0.0236 0.0023 - 10.094 101.887 C6 * -0.0159 0.0021 - 7.557 57.105 C7 * -0.0085 0.0020 - 4.143 17.162 C8 * 0.0884 0.0026 33.687 1134.810 O2 * -0.0229 0.0016 - 14.783 218.527 N1 - 0.3852 0.0019 - 198.121 39252.105 O1 - 0.2706 0.0018 - 151.577 22975.512 ============ Sum((d/s)**2) for starred atoms 1655.122 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarity Plane 2 m1 = 0.34347(0.00083) m2 = -0.37088(0.00093) m3 = -0.86283(0.00035) D = -12.13015(0.00796) Atom d s d/s (d/s)**2 C9 * -0.0197 0.0022 - 9.077 82.396 C10 * 0.0154 0.0022 6.965 48.507 C11 * 0.0122 0.0025 4.953 24.530 C12 * -0.0012 0.0030 - 0.401 0.161 C13 * -0.0267 0.0031 - 8.604 74.026 C14 * -0.0083 0.0031 - 2.662 7.086 C15 * 0.0187 0.0026 7.232 52.303 ============ Sum((d/s)**2) for starred atoms 289.009 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity Plane 3 m1 = 0.78942(0.00088) m2 = -0.07504(0.00299) m3 = 0.60924(0.00133) D = 5.86175(0.03322) Atom d s d/s (d/s)**2 O1 * 0.0000 0.0018 0.000 0.000 N1 * 0.0000 0.0019 0.000 0.000 C1 * 0.0000 0.0021 0.000 0.000 C9 0.0489 0.0022 22.155 490.826 C2 - 0.0912 0.0020 - 45.470 2067.499 ============ Sum((d/s)**2) for starred atoms 0.000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 87.94 (0.05) 92.06 (0.05) 1 3 23.04 (0.17) 156.96 (0.17) 2 3 76.90 (0.10) 103.10 (0.10) #===================================================================== |
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 | ||
N1 | 0.0384 (2) | 0.60399 (16) | 0.46703 (9) | 0.0594 (6) | |
O1 | −0.04754 (19) | 0.62133 (14) | 0.51858 (8) | 0.0760 (6) | |
H1 | −0.0654 | 0.5620 | 0.5349 | 0.114* | |
O2 | 0.43137 (16) | 0.82951 (13) | 0.30324 (7) | 0.0659 (5) | |
C1 | 0.0879 (2) | 0.6926 (2) | 0.44421 (10) | 0.0489 (6) | |
C2 | 0.1715 (2) | 0.67863 (18) | 0.38728 (9) | 0.0445 (5) | |
C3 | 0.1560 (2) | 0.58610 (18) | 0.35011 (10) | 0.0544 (6) | |
H3 | 0.0926 | 0.5320 | 0.3609 | 0.065* | |
C4 | 0.2344 (3) | 0.57431 (19) | 0.29738 (11) | 0.0615 (7) | |
H4 | 0.2235 | 0.5116 | 0.2730 | 0.074* | |
C5 | 0.3289 (2) | 0.65320 (19) | 0.27962 (11) | 0.0557 (6) | |
H5 | 0.3818 | 0.6439 | 0.2439 | 0.067* | |
C6 | 0.3429 (2) | 0.74521 (18) | 0.31568 (10) | 0.0467 (6) | |
C7 | 0.2653 (2) | 0.75760 (18) | 0.36914 (9) | 0.0478 (6) | |
H7 | 0.2766 | 0.8204 | 0.3933 | 0.057* | |
C8 | 0.5054 (3) | 0.8267 (2) | 0.24622 (12) | 0.0779 (8) | |
H8A | 0.5637 | 0.7629 | 0.2454 | 0.117* | |
H8B | 0.5607 | 0.8920 | 0.2426 | 0.117* | |
H8C | 0.4417 | 0.8234 | 0.2121 | 0.117* | |
C9 | 0.0622 (2) | 0.80492 (18) | 0.47080 (10) | 0.0550 (6) | |
H9A | 0.1481 | 0.8456 | 0.4715 | 0.066* | |
H9B | 0.0305 | 0.7973 | 0.5134 | 0.066* | |
C10 | −0.0429 (2) | 0.8697 (2) | 0.43428 (10) | 0.0521 (6) | |
C11 | −0.0157 (3) | 0.9746 (2) | 0.41389 (11) | 0.0675 (7) | |
H11 | 0.0702 | 1.0057 | 0.4214 | 0.081* | |
C12 | −0.1143 (4) | 1.0343 (2) | 0.38237 (13) | 0.0865 (9) | |
H12 | −0.0945 | 1.1050 | 0.3683 | 0.104* | |
C13 | −0.2407 (4) | 0.9894 (3) | 0.37188 (13) | 0.0948 (11) | |
H13 | −0.3081 | 1.0301 | 0.3515 | 0.114* | |
C14 | −0.2683 (3) | 0.8851 (3) | 0.39125 (14) | 0.0893 (9) | |
H14 | −0.3541 | 0.8542 | 0.3836 | 0.107* | |
C15 | −0.1697 (3) | 0.8255 (2) | 0.42201 (12) | 0.0712 (8) | |
H15 | −0.1892 | 0.7540 | 0.4347 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0648 (13) | 0.0630 (15) | 0.0505 (12) | 0.0077 (11) | 0.0185 (11) | 0.0045 (10) |
O1 | 0.0870 (13) | 0.0768 (13) | 0.0642 (11) | 0.0126 (11) | 0.0319 (10) | 0.0082 (10) |
O2 | 0.0643 (10) | 0.0621 (11) | 0.0713 (11) | −0.0145 (9) | 0.0174 (9) | −0.0095 (9) |
C1 | 0.0479 (13) | 0.0545 (16) | 0.0444 (13) | 0.0064 (12) | −0.0006 (11) | −0.0007 (12) |
C2 | 0.0459 (12) | 0.0463 (14) | 0.0412 (12) | 0.0052 (11) | −0.0018 (11) | −0.0023 (11) |
C3 | 0.0598 (15) | 0.0489 (15) | 0.0545 (15) | −0.0042 (12) | 0.0095 (12) | −0.0043 (12) |
C4 | 0.0719 (17) | 0.0482 (15) | 0.0642 (17) | −0.0046 (13) | 0.0103 (14) | −0.0183 (13) |
C5 | 0.0572 (15) | 0.0560 (16) | 0.0537 (14) | 0.0020 (12) | 0.0122 (12) | −0.0116 (13) |
C6 | 0.0426 (12) | 0.0456 (14) | 0.0520 (14) | −0.0016 (12) | −0.0013 (11) | −0.0006 (12) |
C7 | 0.0502 (13) | 0.0470 (14) | 0.0461 (14) | 0.0005 (12) | −0.0011 (11) | −0.0108 (11) |
C8 | 0.0775 (19) | 0.0750 (19) | 0.0812 (19) | −0.0119 (15) | 0.0259 (16) | 0.0026 (16) |
C9 | 0.0608 (15) | 0.0595 (16) | 0.0447 (13) | 0.0058 (13) | 0.0042 (12) | −0.0085 (12) |
C10 | 0.0578 (15) | 0.0558 (16) | 0.0427 (13) | 0.0064 (12) | 0.0098 (12) | −0.0042 (12) |
C11 | 0.0804 (18) | 0.0583 (18) | 0.0639 (17) | 0.0016 (15) | 0.0080 (14) | −0.0041 (14) |
C12 | 0.117 (3) | 0.069 (2) | 0.074 (2) | 0.026 (2) | 0.0136 (19) | 0.0142 (16) |
C13 | 0.092 (2) | 0.120 (3) | 0.072 (2) | 0.045 (2) | 0.0088 (19) | 0.022 (2) |
C14 | 0.0583 (18) | 0.123 (3) | 0.087 (2) | 0.0066 (19) | −0.0025 (16) | 0.020 (2) |
C15 | 0.0594 (16) | 0.083 (2) | 0.0710 (17) | 0.0007 (16) | 0.0043 (15) | 0.0148 (15) |
N1—C1 | 1.276 (3) | C8—H8A | 0.9600 |
N1—O1 | 1.404 (2) | C8—H8B | 0.9600 |
O1—H1 | 0.8200 | C8—H8C | 0.9600 |
O2—C6 | 1.363 (2) | C9—C10 | 1.509 (3) |
O2—C8 | 1.422 (3) | C9—H9A | 0.9700 |
C1—C2 | 1.479 (3) | C9—H9B | 0.9700 |
C1—C9 | 1.500 (3) | C10—C15 | 1.370 (3) |
C2—C7 | 1.379 (3) | C10—C11 | 1.372 (3) |
C2—C3 | 1.387 (3) | C11—C12 | 1.380 (4) |
C3—C4 | 1.373 (3) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.363 (4) |
C4—C5 | 1.381 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.360 (4) |
C5—C6 | 1.366 (3) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.371 (4) |
C6—C7 | 1.383 (3) | C14—H14 | 0.9300 |
C7—H7 | 0.9300 | C15—H15 | 0.9300 |
C1—N1—O1 | 113.68 (18) | O2—C8—H8C | 109.5 |
N1—O1—H1 | 109.5 | H8A—C8—H8C | 109.5 |
C6—O2—C8 | 118.06 (18) | H8B—C8—H8C | 109.5 |
N1—C1—C2 | 115.4 (2) | C1—C9—C10 | 112.84 (18) |
N1—C1—C9 | 123.9 (2) | C1—C9—H9A | 109.0 |
C2—C1—C9 | 120.7 (2) | C10—C9—H9A | 109.0 |
C7—C2—C3 | 118.1 (2) | C1—C9—H9B | 109.0 |
C7—C2—C1 | 121.2 (2) | C10—C9—H9B | 109.0 |
C3—C2—C1 | 120.7 (2) | H9A—C9—H9B | 107.8 |
C4—C3—C2 | 120.0 (2) | C15—C10—C11 | 118.4 (2) |
C4—C3—H3 | 120.0 | C15—C10—C9 | 120.3 (2) |
C2—C3—H3 | 120.0 | C11—C10—C9 | 121.3 (2) |
C3—C4—C5 | 121.7 (2) | C10—C11—C12 | 120.7 (3) |
C3—C4—H4 | 119.2 | C10—C11—H11 | 119.6 |
C5—C4—H4 | 119.2 | C12—C11—H11 | 119.6 |
C6—C5—C4 | 118.5 (2) | C13—C12—C11 | 119.8 (3) |
C6—C5—H5 | 120.8 | C13—C12—H12 | 120.1 |
C4—C5—H5 | 120.8 | C11—C12—H12 | 120.1 |
O2—C6—C5 | 124.4 (2) | C14—C13—C12 | 119.9 (3) |
O2—C6—C7 | 115.17 (19) | C14—C13—H13 | 120.0 |
C5—C6—C7 | 120.4 (2) | C12—C13—H13 | 120.0 |
C2—C7—C6 | 121.3 (2) | C13—C14—C15 | 120.1 (3) |
C2—C7—H7 | 119.3 | C13—C14—H14 | 119.9 |
C6—C7—H7 | 119.3 | C15—C14—H14 | 119.9 |
O2—C8—H8A | 109.5 | C10—C15—C14 | 121.0 (3) |
O2—C8—H8B | 109.5 | C10—C15—H15 | 119.5 |
H8A—C8—H8B | 109.5 | C14—C15—H15 | 119.5 |
O1—N1—C1—C2 | −176.09 (17) | C1—C2—C7—C6 | −179.50 (19) |
O1—N1—C1—C9 | 2.3 (3) | O2—C6—C7—C2 | 179.88 (18) |
N1—C1—C2—C7 | −159.0 (2) | C5—C6—C7—C2 | −0.5 (3) |
C9—C1—C2—C7 | 22.6 (3) | N1—C1—C9—C10 | −102.7 (3) |
N1—C1—C2—C3 | 22.0 (3) | C2—C1—C9—C10 | 75.6 (3) |
C9—C1—C2—C3 | −156.4 (2) | C1—C9—C10—C15 | 53.3 (3) |
C7—C2—C3—C4 | 0.9 (3) | C1—C9—C10—C11 | −128.3 (2) |
C1—C2—C3—C4 | 180.0 (2) | C15—C10—C11—C12 | 0.7 (4) |
C2—C3—C4—C5 | −0.5 (4) | C9—C10—C11—C12 | −177.8 (2) |
C3—C4—C5—C6 | −0.5 (4) | C10—C11—C12—C13 | 0.7 (4) |
C8—O2—C6—C5 | 5.8 (3) | C11—C12—C13—C14 | −1.5 (5) |
C8—O2—C6—C7 | −174.5 (2) | C12—C13—C14—C15 | 0.8 (5) |
C4—C5—C6—O2 | −179.5 (2) | C11—C10—C15—C14 | −1.3 (4) |
C4—C5—C6—C7 | 0.9 (3) | C9—C10—C15—C14 | 177.1 (2) |
C3—C2—C7—C6 | −0.4 (3) | C13—C14—C15—C10 | 0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O1 | 0.97 | 2.27 | 2.676 (3) | 104 |
O1—H1···N1i | 0.82 | 2.03 | 2.754 (3) | 147 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO2 |
Mr | 241.28 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 295 |
a, b, c (Å) | 9.7198 (9), 12.139 (1), 21.499 (2) |
V (Å3) | 2536.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.901, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18438, 2489, 1358 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.118, 1.01 |
No. of reflections | 2489 |
No. of parameters | 165 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.11 |
Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97 and PLATON.
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O1 | 0.97 | 2.27 | 2.676 (3) | 104 |
O1—H1···N1i | 0.82 | 2.03 | 2.754 (3) | 147 |
Symmetry code: (i) −x, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
As a part of our interest in the design of candidate cytotoxins, based on the α, β-unsaturated keto scaffold, a series of compounds have been synthesized. These molecules have been shown to alkylate thiols but not amino or hydroxyl substituents; the latter two functional groups are found in nucleic acids suggesting that enones may be devoid of unwanted genetic mutations causing genotoxic properties, that is common among a number of anticancer drugs currently in use (Pati et al., 2007a) Pati et al., 2007b). The title molecule, C15H15NO2, (I), is one such compound, synthesized from structurally similar substituted desoxybenzoin precursor.
The three dimensional structure is composed of three planar subunits, namely, methoxyphenyl (O2/C1—C8), phenylethanone (C9—C15) and oxime (O1/N1/C1). The former two planes, on either side of oxime subunit make an angle of 87.9 (1)°, whereas the oxime subunit is oriented by 23.0 (2)° and 76.9 (1)° with respect to the first and second planes. Molecular structure is shown Fig. 1.
An intra-molecular C9B—H9B···O1 hydrogen bond stabilize the structure. O1 also participate in O1—H1···N1 hydrogen bond with another oxime subunit in the molecules related by (-x, 1 - y, 1 - z) (Table 1). The O—H···N hydrogen bonds cluster molecules into R22(6) dimers. There is a good Cg2···Cg2 stacking interaction, with the second Cg2 at (-x, 2 - y, 1 - z). The benzene rings are parallel to each other, 3.344 Å apart with a slippage of 4.107 Å. Cg2 is the centroid of the (C10—C15) ring. The center-to-center distance is 5.297 (2) Å. The intermolecular hydrogen bond and aromatic interactions interlink molecules into a one-dimensional array along b axis, as illustrated in Fig. 2. Two short contacts, i.e., C8—H8A..Cg1 [H···Cg = 2.74 Å, C—H···Cg = 138°] C8—H8C···Cg2 [H···Cg = 2.90 Å, C—H···Cg = 144°] were also observed in the crystal, where Cg1 (centroid of C2—C7 ring) and Cg2 are situated in the molecule at the symmetry position (1/2 + x, y, 1/2 - z). However, it is unlikely to have any structural significance, as methyl group is undergoing extremely rapid rotation about O2—C8.