Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006360/na6157sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006360/na6157Isup2.hkl |
CCDC reference: 185781
Key indicators
- Single-crystal X-ray study
- T = 250 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.156
- Data-to-parameter ratio = 15.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 75.00 From the CIF: _reflns_number_total 3176 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3360 Completeness (_total/calc) 94.52% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was prepared from dimethyldopamine and trans-cinnamoyl chloride through solvent-free reaction (Ito et al., 2001). Crystals of (I) were grown from an acetone solution.
The relatively low completeness (0.945 for θmax=75°) is a result of the blind region of the low-temperature apparatus. All H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom).
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level. | |
Fig. 2. The projection of the crystal structure of (I) along b. |
C19H21NO3 | F(000) = 664 |
Mr = 311.38 | Dx = 1.275 Mg m−3 |
Monoclinic, P21/a | Cu Kα radiation, λ = 1.5418 Å |
a = 24.449 (2) Å | Cell parameters from 25 reflections |
b = 5.2431 (5) Å | θ = 25.0–30.0° |
c = 12.6633 (9) Å | µ = 0.69 mm−1 |
β = 91.714 (6)° | T = 250 K |
V = 1622.6 (2) Å3 | Needle, colourless |
Z = 4 | 0.75 × 0.15 × 0.05 mm |
Rigaku AFC-7R diffractometer | Rint = 0.025 |
θ–2θ scans | θmax = 75°, θmin = 2.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→30 |
Tmin = 0.842, Tmax = 0.965 | k = −6→0 |
4079 measured reflections | l = −15→15 |
3176 independent reflections | 3 standard reflections every 150 reflections |
2641 reflections with I > 2σ(I) | intensity decay: 8.1% |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0408P)2 + 1.4606P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max = 0.001 |
wR(F2) = 0.156 | Δρmax = 0.28 e Å−3 |
S = 1.26 | Δρmin = −0.25 e Å−3 |
3176 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
209 parameters | Extinction coefficient: 0.0028 (3) |
H-atom parameters constrained |
C19H21NO3 | V = 1622.6 (2) Å3 |
Mr = 311.38 | Z = 4 |
Monoclinic, P21/a | Cu Kα radiation |
a = 24.449 (2) Å | µ = 0.69 mm−1 |
b = 5.2431 (5) Å | T = 250 K |
c = 12.6633 (9) Å | 0.75 × 0.15 × 0.05 mm |
β = 91.714 (6)° |
Rigaku AFC-7R diffractometer | 2641 reflections with I > 2σ(I) |
Absorption correction: integration (Coppens et al., 1965) | Rint = 0.025 |
Tmin = 0.842, Tmax = 0.965 | 3 standard reflections every 150 reflections |
4079 measured reflections | intensity decay: 8.1% |
3176 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 209 parameters |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.26 | Δρmax = 0.28 e Å−3 |
3176 reflections | Δρmin = −0.25 e Å−3 |
Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.42822 (8) | 0.6551 (4) | 0.0621 (2) | 0.0519 (5) | |
O2 | 0.67592 (7) | −0.1566 (4) | 0.4609 (1) | 0.0500 (5) | |
O3 | 0.61383 (7) | 0.1929 (4) | 0.5347 (1) | 0.0539 (5) | |
N4 | 0.43206 (8) | 0.2244 (4) | 0.0733 (2) | 0.0456 (5) | |
C5 | 0.1854 (1) | 0.6130 (6) | −0.2582 (2) | 0.0469 (6) | |
C6 | 0.1942 (1) | 0.4245 (6) | −0.1840 (2) | 0.0459 (6) | |
C7 | 0.2423 (1) | 0.4186 (5) | −0.1235 (2) | 0.0404 (6) | |
C8 | 0.28253 (9) | 0.6035 (5) | −0.1365 (2) | 0.0349 (5) | |
C9 | 0.2724 (1) | 0.7964 (5) | −0.2101 (2) | 0.0440 (6) | |
C10 | 0.2243 (1) | 0.7998 (5) | −0.2711 (2) | 0.0489 (6) | |
C11 | 0.3344 (1) | 0.6020 (5) | −0.0747 (2) | 0.0375 (5) | |
C12 | 0.3553 (1) | 0.4147 (5) | −0.0169 (2) | 0.0385 (5) | |
C13 | 0.4084 (1) | 0.4435 (5) | 0.0432 (2) | 0.0374 (5) | |
C14 | 0.4841 (1) | 0.2087 (6) | 0.1330 (2) | 0.0525 (7) | |
C15 | 0.4771 (1) | 0.0830 (6) | 0.2386 (2) | 0.0516 (7) | |
C16 | 0.53078 (9) | 0.0195 (5) | 0.2959 (2) | 0.0409 (6) | |
C17 | 0.5645 (1) | −0.1684 (6) | 0.2576 (2) | 0.0446 (6) | |
C18 | 0.6133 (1) | −0.2338 (5) | 0.3106 (2) | 0.0422 (6) | |
C19 | 0.62896 (9) | −0.1088 (5) | 0.4026 (2) | 0.0377 (5) | |
C20 | 0.59536 (9) | 0.0827 (5) | 0.4425 (2) | 0.0374 (5) | |
C21 | 0.5469 (1) | 0.1451 (5) | 0.3887 (2) | 0.0408 (6) | |
C22 | 0.7096 (1) | −0.3586 (6) | 0.4246 (2) | 0.0495 (7) | |
C23 | 0.5813 (1) | 0.3872 (6) | 0.5787 (2) | 0.0523 (7) | |
H4 | 0.4140 | 0.0695 | 0.0549 | 0.0547* | |
H5 | 0.1526 | 0.6142 | −0.3005 | 0.0562* | |
H6 | 0.1670 | 0.2978 | −0.1742 | 0.0551* | |
H7 | 0.2479 | 0.2873 | −0.0726 | 0.0485* | |
H9 | 0.2987 | 0.9275 | −0.2186 | 0.0527* | |
H10 | 0.2182 | 0.9311 | −0.3218 | 0.0587* | |
H11 | 0.3554 | 0.7544 | −0.0767 | 0.0450* | |
H12 | 0.3361 | 0.2575 | −0.0135 | 0.0462* | |
H14A | 0.4980 | 0.3760 | 0.1438 | 0.0629* | |
H14B | 0.5092 | 0.1120 | 0.0936 | 0.0629* | |
H15A | 0.4569 | 0.1949 | 0.2818 | 0.0619* | |
H15B | 0.4571 | −0.0708 | 0.2279 | 0.0619* | |
H17 | 0.5542 | −0.2546 | 0.1941 | 0.0534* | |
H18 | 0.6358 | −0.3644 | 0.2833 | 0.0506* | |
H21 | 0.5243 | 0.2759 | 0.4156 | 0.0490* | |
H22A | 0.6895 | −0.5136 | 0.4242 | 0.0593* | |
H22B | 0.7409 | −0.3748 | 0.4703 | 0.0593* | |
H22C | 0.7209 | −0.3216 | 0.3550 | 0.0593* | |
H23A | 0.5462 | 0.3202 | 0.5937 | 0.0627* | |
H23B | 0.5985 | 0.4477 | 0.6421 | 0.0627* | |
H23C | 0.5773 | 0.5238 | 0.5298 | 0.0627* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.051 (1) | 0.040 (1) | 0.064 (1) | −0.0040 (8) | −0.0139 (9) | −0.0034 (9) |
O2 | 0.0405 (9) | 0.062 (1) | 0.0468 (10) | 0.0141 (9) | −0.0136 (8) | −0.0122 (9) |
O3 | 0.051 (1) | 0.065 (1) | 0.0446 (10) | 0.0138 (9) | −0.0140 (8) | −0.0208 (9) |
N4 | 0.039 (1) | 0.040 (1) | 0.057 (1) | −0.0034 (9) | −0.0161 (10) | 0.005 (1) |
C5 | 0.041 (1) | 0.056 (2) | 0.044 (1) | 0.010 (1) | −0.007 (1) | −0.005 (1) |
C6 | 0.038 (1) | 0.053 (2) | 0.046 (1) | −0.001 (1) | −0.001 (1) | −0.001 (1) |
C7 | 0.042 (1) | 0.043 (1) | 0.036 (1) | 0.002 (1) | 0.0010 (10) | 0.005 (1) |
C8 | 0.040 (1) | 0.035 (1) | 0.029 (1) | 0.0042 (10) | 0.0002 (9) | −0.0034 (9) |
C9 | 0.048 (1) | 0.039 (1) | 0.045 (1) | 0.000 (1) | −0.003 (1) | 0.003 (1) |
C10 | 0.055 (2) | 0.048 (2) | 0.043 (1) | 0.007 (1) | −0.009 (1) | 0.008 (1) |
C11 | 0.040 (1) | 0.037 (1) | 0.036 (1) | −0.001 (1) | −0.0021 (10) | −0.0034 (10) |
C12 | 0.038 (1) | 0.037 (1) | 0.040 (1) | −0.003 (1) | −0.0032 (10) | −0.001 (1) |
C13 | 0.039 (1) | 0.039 (1) | 0.034 (1) | −0.002 (1) | −0.0012 (10) | −0.0018 (10) |
C14 | 0.036 (1) | 0.055 (2) | 0.066 (2) | −0.005 (1) | −0.014 (1) | 0.012 (1) |
C15 | 0.034 (1) | 0.077 (2) | 0.043 (1) | 0.005 (1) | −0.007 (1) | −0.007 (1) |
C16 | 0.033 (1) | 0.054 (2) | 0.035 (1) | −0.002 (1) | −0.0030 (10) | 0.001 (1) |
C17 | 0.041 (1) | 0.056 (2) | 0.037 (1) | −0.004 (1) | −0.006 (1) | −0.009 (1) |
C18 | 0.039 (1) | 0.047 (1) | 0.040 (1) | 0.002 (1) | −0.001 (1) | −0.007 (1) |
C19 | 0.032 (1) | 0.044 (1) | 0.037 (1) | −0.0012 (10) | −0.0042 (9) | 0.001 (1) |
C20 | 0.038 (1) | 0.041 (1) | 0.033 (1) | −0.001 (1) | −0.0038 (9) | −0.0037 (10) |
C21 | 0.036 (1) | 0.049 (1) | 0.037 (1) | 0.007 (1) | −0.0008 (10) | −0.002 (1) |
C22 | 0.040 (1) | 0.055 (2) | 0.053 (2) | 0.011 (1) | −0.006 (1) | −0.002 (1) |
C23 | 0.058 (2) | 0.052 (2) | 0.046 (1) | 0.004 (1) | −0.002 (1) | −0.014 (1) |
O1—C13 | 1.231 (3) | C12—H12 | 0.950 |
O2—C19 | 1.369 (3) | C14—C15 | 1.505 (4) |
O2—C22 | 1.426 (3) | C14—H14A | 0.950 |
O3—C20 | 1.367 (3) | C14—H14B | 0.950 |
O3—C23 | 1.417 (4) | C15—C16 | 1.518 (3) |
N4—C13 | 1.337 (3) | C15—H15A | 0.950 |
N4—C14 | 1.461 (3) | C15—H15B | 0.950 |
N4—H4 | 0.950 | C16—C17 | 1.382 (4) |
C5—C6 | 1.376 (4) | C16—C21 | 1.394 (3) |
C5—C10 | 1.378 (4) | C17—C18 | 1.393 (3) |
C5—H5 | 0.950 | C17—H17 | 0.950 |
C6—C7 | 1.385 (3) | C18—C19 | 1.382 (3) |
C6—H6 | 0.950 | C18—H18 | 0.950 |
C7—C8 | 1.395 (3) | C19—C20 | 1.401 (3) |
C7—H7 | 0.950 | C20—C21 | 1.388 (3) |
C8—C9 | 1.392 (3) | C21—H21 | 0.950 |
C8—C11 | 1.470 (3) | C22—H22A | 0.950 |
C9—C10 | 1.388 (4) | C22—H22B | 0.950 |
C9—H9 | 0.950 | C22—H22C | 0.950 |
C10—H10 | 0.950 | C23—H23A | 0.950 |
C11—C12 | 1.319 (3) | C23—H23B | 0.950 |
C11—H11 | 0.950 | C23—H23C | 0.950 |
C12—C13 | 1.492 (3) | ||
C19—O2—C22 | 116.5 (2) | H14A—C14—H14B | 109.5 |
C20—O3—C23 | 117.7 (2) | C14—C15—C16 | 113.6 (2) |
C13—N4—C14 | 123.9 (2) | C14—C15—H15A | 108.4 |
C13—N4—H4 | 118.0 | C14—C15—H15B | 108.4 |
C14—N4—H4 | 118.0 | C16—C15—H15A | 108.4 |
C6—C5—C10 | 119.8 (2) | C16—C15—H15B | 108.4 |
C6—C5—H5 | 120.1 | H15A—C15—H15B | 109.5 |
C10—C5—H5 | 120.1 | C15—C16—C17 | 120.4 (2) |
C5—C6—C7 | 120.4 (2) | C15—C16—C21 | 121.2 (2) |
C5—C6—H6 | 119.8 | C17—C16—C21 | 118.4 (2) |
C7—C6—H6 | 119.8 | C16—C17—C18 | 121.2 (2) |
C6—C7—C8 | 120.6 (2) | C16—C17—H17 | 119.4 |
C6—C7—H7 | 119.7 | C18—C17—H17 | 119.4 |
C8—C7—H7 | 119.7 | C17—C18—C19 | 120.1 (2) |
C7—C8—C9 | 118.1 (2) | C17—C18—H18 | 120.0 |
C7—C8—C11 | 122.3 (2) | C19—C18—H18 | 119.9 |
C9—C8—C11 | 119.6 (2) | O2—C19—C18 | 125.1 (2) |
C8—C9—C10 | 120.9 (2) | O2—C19—C20 | 115.4 (2) |
C8—C9—H9 | 119.6 | C18—C19—C20 | 119.5 (2) |
C10—C9—H9 | 119.5 | O3—C20—C19 | 115.3 (2) |
C5—C10—C9 | 120.0 (2) | O3—C20—C21 | 125.1 (2) |
C5—C10—H10 | 120.0 | C19—C20—C21 | 119.6 (2) |
C9—C10—H10 | 120.0 | C16—C21—C20 | 121.2 (2) |
C8—C11—C12 | 127.8 (2) | C16—C21—H21 | 119.4 |
C8—C11—H11 | 116.1 | C20—C21—H21 | 119.4 |
C12—C11—H11 | 116.1 | O2—C22—H22A | 109.5 |
C11—C12—C13 | 121.7 (2) | O2—C22—H22B | 109.5 |
C11—C12—H12 | 119.2 | O2—C22—H22C | 109.5 |
C13—C12—H12 | 119.2 | H22A—C22—H22B | 109.5 |
O1—C13—N4 | 123.7 (2) | H22A—C22—H22C | 109.5 |
O1—C13—C12 | 121.4 (2) | H22B—C22—H22C | 109.5 |
N4—C13—C12 | 114.9 (2) | O3—C23—H23A | 109.5 |
N4—C14—C15 | 111.3 (2) | O3—C23—H23B | 109.5 |
N4—C14—H14A | 109.0 | O3—C23—H23C | 109.5 |
N4—C14—H14B | 109.0 | H23A—C23—H23B | 109.5 |
C15—C14—H14A | 109.0 | H23A—C23—H23C | 109.5 |
C15—C14—H14B | 109.0 | H23B—C23—H23C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1i | 0.95 | 2.20 | 2.990 (3) | 140 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H21NO3 |
Mr | 311.38 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 250 |
a, b, c (Å) | 24.449 (2), 5.2431 (5), 12.6633 (9) |
β (°) | 91.714 (6) |
V (Å3) | 1622.6 (2) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.75 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | Integration (Coppens et al., 1965) |
Tmin, Tmax | 0.842, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4079, 3176, 2641 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.156, 1.26 |
No. of reflections | 3176 |
No. of parameters | 209 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.25 |
Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), WinAFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.
O1—C13 | 1.231 (3) | C11—C12 | 1.319 (3) |
N4—C13 | 1.337 (3) | C12—C13 | 1.492 (3) |
N4—C14 | 1.461 (3) | C14—C15 | 1.505 (4) |
C8—C11 | 1.470 (3) | C15—C16 | 1.518 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1i | 0.95 | 2.20 | 2.990 (3) | 140 |
Symmetry code: (i) x, y−1, z. |
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Solid-state photochemistry of some dopamine derivatives was investigated by Ito et al. (2001). The crystal structure of the photostable title compound, (I), has been determined to investigate the geometrical factors which prevent the [2 + 2] photodimerization.
The shortest intermolecular distance between the C═C double bonds of the cinnamoyl moieties is 5.087 (4) Å for C12···C11(1/2 - x, 1/2 + y, -z), and the center-to-center distance of the C═C double bonds is 5.483 (4) Å for this pair. These molecules are related by 21 screw axis parallel to b, and the C═C bond axes are criss-crossed with each other, making a torsion angle of 83.8 (2)° (Fig. 2). Intermolecular N—H···O hydrogen bonds form a linear chain along b (Table 2).