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The title compound, C
6H
5COCH=C(NHCH
2CH
2OH)CH
3 or C
12H
15NO
2, has been synthesized by the reaction of benzoylacetone and ethanolamine in ethanol. In the crystalline state, molecules are linked by intermolecular hydrogen bonds (O—H
O=C) to form centrosymmetric
R22(14) dimers.
Supporting information
CCDC reference: 277278
Key indicators
- Single-crystal X-ray study
- T = 293 K
- R factor = 0.071
- wR factor = 0.220
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
3-(Hydroxyethylamino)-1-phenylbut-2-en-1-one
top
Crystal data top
C12H15NO2 | F(000) = 440 |
Mr = 205.25 | Dx = 1.196 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 5.6330 (11) Å | θ = 10–13° |
b = 25.961 (5) Å | µ = 0.08 mm−1 |
c = 7.9770 (16) Å | T = 293 K |
β = 102.26 (3)° | Block, colorless |
V = 1139.9 (4) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1044 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
ω/2θ scans | h = 0→6 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→31 |
Tmin = 0.955, Tmax = 0.976 | l = −9→9 |
2449 measured reflections | 3 standard reflections every 200 reflections |
2224 independent reflections | intensity decay: none |
Refinement top
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)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.08P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
2224 reflections | Δρmax = 0.32 e Å−3 |
137 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.065 (8) |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.0052 (4) | −0.01119 (10) | 0.7678 (3) | 0.0753 (9) | |
Ho | 1.0553 | −0.0344 | 0.7150 | 0.113* | |
O2 | 0.8199 (4) | 0.08835 (10) | 0.4083 (3) | 0.0713 (8) | |
N | 0.6354 (5) | 0.06123 (12) | 0.6757 (3) | 0.0616 (9) | |
Hn | 0.7361 | 0.0550 | 0.6109 | 0.074* | |
C1 | 0.7635 (7) | −0.02264 (16) | 0.7842 (5) | 0.0720 (11) | |
H1a | 0.7676 | −0.0465 | 0.8784 | 0.086* | |
H1b | 0.6750 | −0.0388 | 0.6798 | 0.086* | |
C2 | 0.6388 (7) | 0.02580 (15) | 0.8167 (5) | 0.0675 (11) | |
H2a | 0.4739 | 0.0182 | 0.8270 | 0.081* | |
H2b | 0.7239 | 0.0413 | 0.9232 | 0.081* | |
C3 | 0.3060 (7) | 0.11262 (17) | 0.7411 (5) | 0.0793 (13) | |
H3a | 0.3168 | 0.0869 | 0.8290 | 0.119* | |
H3b | 0.1470 | 0.1117 | 0.6680 | 0.119* | |
H3c | 0.3344 | 0.1460 | 0.7931 | 0.119* | |
C4 | 0.4946 (6) | 0.10189 (15) | 0.6362 (4) | 0.0582 (9) | |
C5 | 0.5131 (6) | 0.13388 (14) | 0.5004 (5) | 0.0620 (10) | |
H5 | 0.4147 | 0.1630 | 0.4821 | 0.074* | |
C6 | 0.6720 (6) | 0.12509 (14) | 0.3879 (4) | 0.0555 (9) | |
C7 | 0.6630 (6) | 0.15994 (14) | 0.2374 (4) | 0.0574 (9) | |
C8 | 0.4894 (8) | 0.19711 (18) | 0.1884 (6) | 0.0915 (14) | |
H8 | 0.3719 | 0.2017 | 0.2532 | 0.110* | |
C9 | 0.4824 (10) | 0.2278 (2) | 0.0470 (7) | 0.1073 (17) | |
H9 | 0.3641 | 0.2532 | 0.0199 | 0.129* | |
C10 | 0.6466 (10) | 0.2214 (2) | −0.0533 (7) | 0.0989 (16) | |
H10 | 0.6392 | 0.2414 | −0.1510 | 0.119* | |
C11 | 0.8222 (9) | 0.1850 (2) | −0.0079 (7) | 0.1088 (18) | |
H11 | 0.9380 | 0.1809 | −0.0744 | 0.131* | |
C12 | 0.8329 (7) | 0.15384 (17) | 0.1353 (6) | 0.0819 (13) | |
H12 | 0.9536 | 0.1289 | 0.1628 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0596 (15) | 0.0871 (19) | 0.0840 (19) | 0.0027 (14) | 0.0257 (13) | −0.0078 (15) |
O2 | 0.0566 (15) | 0.0903 (19) | 0.0739 (17) | 0.0182 (15) | 0.0296 (12) | 0.0108 (14) |
N | 0.0498 (17) | 0.083 (2) | 0.0566 (18) | 0.0056 (16) | 0.0218 (14) | 0.0040 (16) |
C1 | 0.066 (2) | 0.088 (3) | 0.066 (2) | −0.008 (2) | 0.0216 (19) | 0.009 (2) |
C2 | 0.056 (2) | 0.090 (3) | 0.060 (2) | 0.003 (2) | 0.0208 (18) | 0.007 (2) |
C3 | 0.068 (3) | 0.104 (3) | 0.075 (3) | 0.013 (2) | 0.037 (2) | −0.005 (2) |
C4 | 0.0433 (19) | 0.074 (2) | 0.060 (2) | 0.0006 (18) | 0.0177 (16) | −0.0075 (19) |
C5 | 0.058 (2) | 0.067 (2) | 0.065 (2) | 0.0073 (18) | 0.0236 (18) | −0.0034 (19) |
C6 | 0.0419 (18) | 0.066 (2) | 0.060 (2) | 0.0010 (18) | 0.0142 (15) | −0.0053 (18) |
C7 | 0.050 (2) | 0.065 (2) | 0.059 (2) | −0.0053 (18) | 0.0148 (17) | −0.0045 (18) |
C8 | 0.095 (3) | 0.098 (3) | 0.091 (3) | 0.034 (3) | 0.043 (3) | 0.020 (3) |
C9 | 0.118 (4) | 0.100 (4) | 0.107 (4) | 0.028 (3) | 0.032 (3) | 0.035 (3) |
C10 | 0.096 (4) | 0.099 (4) | 0.102 (4) | −0.020 (3) | 0.023 (3) | 0.036 (3) |
C11 | 0.094 (4) | 0.138 (5) | 0.109 (4) | −0.012 (4) | 0.054 (3) | 0.036 (4) |
C12 | 0.065 (3) | 0.093 (3) | 0.097 (3) | 0.005 (2) | 0.038 (2) | 0.017 (3) |
Geometric parameters (Å, º) top
N—C2 | 1.449 (4) | C4—C5 | 1.386 (5) |
N—C4 | 1.318 (4) | C5—C6 | 1.414 (4) |
N—Hn | 0.8600 | C5—H5 | 0.9300 |
O1—C1 | 1.426 (4) | C6—C7 | 1.496 (5) |
O1—Ho | 0.8200 | C7—C8 | 1.370 (5) |
O2—C6 | 1.254 (4) | C7—C12 | 1.391 (5) |
C1—C2 | 1.490 (5) | C8—C9 | 1.375 (6) |
C1—H1a | 0.9700 | C8—H8 | 0.9300 |
C1—H1b | 0.9700 | C9—C10 | 1.355 (7) |
C2—H2a | 0.9700 | C9—H9 | 0.9300 |
C2—H2b | 0.9700 | C10—C11 | 1.360 (6) |
C3—C4 | 1.512 (4) | C10—H10 | 0.9300 |
C3—H3a | 0.9600 | C11—C12 | 1.391 (6) |
C3—H3b | 0.9600 | C11—H11 | 0.9300 |
C3—H3c | 0.9600 | C12—H12 | 0.9300 |
| | | |
C1—O1—Ho | 109.5 | C4—C5—C6 | 124.2 (3) |
C2—N—C4 | 127.0 (3) | C4—C5—H5 | 117.9 |
C2—N—Hn | 116.5 | C6—C5—H5 | 117.9 |
C4—N—Hn | 116.5 | O2—C6—C5 | 122.2 (3) |
O1—C1—C2 | 109.5 (3) | O2—C6—C7 | 118.2 (3) |
O1—C1—H1a | 109.8 | C5—C6—C7 | 119.6 (3) |
C2—C1—H1a | 109.8 | C8—C7—C12 | 116.8 (4) |
O1—C1—H1b | 109.8 | C8—C7—C6 | 123.7 (3) |
C2—C1—H1b | 109.8 | C12—C7—C6 | 119.4 (3) |
H1a—C1—H1b | 108.2 | C7—C8—C9 | 122.4 (4) |
N—C2—C1 | 109.3 (3) | C7—C8—H8 | 118.8 |
N—C2—H2a | 109.8 | C9—C8—H8 | 118.8 |
C1—C2—H2a | 109.8 | C10—C9—C8 | 120.5 (5) |
N—C2—H2b | 109.8 | C10—C9—H9 | 119.7 |
C1—C2—H2b | 109.8 | C8—C9—H9 | 119.7 |
H2a—C2—H2b | 108.3 | C9—C10—C11 | 118.5 (4) |
N—C4—C3 | 118.2 (3) | C9—C10—H10 | 120.7 |
N—C4—C5 | 121.7 (3) | C11—C10—H10 | 120.7 |
C3—C4—C5 | 120.0 (3) | C10—C11—C12 | 121.7 (4) |
C4—C3—H3a | 109.5 | C10—C11—H11 | 119.2 |
C4—C3—H3b | 109.5 | C12—C11—H11 | 119.2 |
H3a—C3—H3b | 109.5 | C11—C12—C7 | 120.0 (4) |
C4—C3—H3c | 109.5 | C11—C12—H12 | 120.0 |
H3a—C3—H3c | 109.5 | C7—C12—H12 | 120.0 |
H3b—C3—H3c | 109.5 | | |
| | | |
C4—N—C2—C1 | 162.3 (3) | O2—C6—C7—C12 | −6.3 (5) |
O1—C1—C2—N | 59.0 (4) | C5—C6—C7—C12 | 174.7 (3) |
C2—N—C4—C5 | 178.1 (3) | C12—C7—C8—C9 | −0.9 (7) |
C2—N—C4—C3 | −3.1 (5) | C6—C7—C8—C9 | −178.5 (4) |
N—C4—C5—C6 | 3.2 (6) | C7—C8—C9—C10 | 1.7 (8) |
C3—C4—C5—C6 | −175.6 (3) | C8—C9—C10—C11 | −2.0 (8) |
C4—C5—C6—O2 | −3.8 (6) | C9—C10—C11—C12 | 1.6 (8) |
C4—C5—C6—C7 | 175.2 (3) | C10—C11—C12—C7 | −0.8 (8) |
O2—C6—C7—C8 | 171.2 (4) | C8—C7—C12—C11 | 0.5 (6) |
C5—C6—C7—C8 | −7.9 (5) | C6—C7—C12—C11 | 178.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—Hn···O1 | 0.86 | 2.45 | 2.786 (4) | 104 |
N—Hn···O2 | 0.86 | 1.98 | 2.658 (4) | 135 |
O1—Ho···O2i | 0.82 | 1.93 | 2.747 (4) | 179 |
C3—H3b···O2ii | 0.96 | 2.54 | 3.443 (5) | 158 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y, z. |
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