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In the crystal structure of the title compound, cinnamoyl di­methyl­dop­amine, C19H21NO3, the shortest distance between the centers of the C=C double bonds in neighboring cinnamoyl moieties is 5.483 (4) Å. Such a long center-to-center distance and the criss-crossed arrangement of the C=C bond axes, with a torsion angle of 83.8 (2)°, contribute to the photostability of the title compound in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006360/na6157sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006360/na6157Isup2.hkl
Contains datablock I

CCDC reference: 185781

Key indicators

  • Single-crystal X-ray study
  • T = 250 K
  • Mean [sigma](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


Yellow Alert 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

Comment top

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 CC 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 CC double bonds is 5.483 (4) Å for this pair. These molecules are related by 21 screw axis parallel to b, and the CC 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).

Experimental top

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.

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The projection of the crystal structure of (I) along b.
(I) top
Crystal data top
C19H21NO3F(000) = 664
Mr = 311.38Dx = 1.275 Mg m3
Monoclinic, P21/aCu Kα radiation, λ = 1.5418 Å
a = 24.449 (2) ÅCell parameters from 25 reflections
b = 5.2431 (5) Åθ = 25.0–30.0°
c = 12.6633 (9) ŵ = 0.69 mm1
β = 91.714 (6)°T = 250 K
V = 1622.6 (2) Å3Needle, colourless
Z = 40.75 × 0.15 × 0.05 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.025
θ–2θ scansθmax = 75°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 030
Tmin = 0.842, Tmax = 0.965k = 60
4079 measured reflectionsl = 1515
3176 independent reflections3 standard reflections every 150 reflections
2641 reflections with I > 2σ(I) intensity decay: 8.1%
Refinement top
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) = 0.156Δρmax = 0.28 e Å3
S = 1.26Δρmin = 0.25 e Å3
3176 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
209 parametersExtinction coefficient: 0.0028 (3)
H-atom parameters constrained
Crystal data top
C19H21NO3V = 1622.6 (2) Å3
Mr = 311.38Z = 4
Monoclinic, P21/aCu Kα radiation
a = 24.449 (2) ŵ = 0.69 mm1
b = 5.2431 (5) ÅT = 250 K
c = 12.6633 (9) Å0.75 × 0.15 × 0.05 mm
β = 91.714 (6)°
Data collection top
Rigaku AFC-7R
diffractometer
2641 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.025
Tmin = 0.842, Tmax = 0.9653 standard reflections every 150 reflections
4079 measured reflections intensity decay: 8.1%
3176 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056209 parameters
wR(F2) = 0.156H-atom parameters constrained
S = 1.26Δρmax = 0.28 e Å3
3176 reflectionsΔρmin = 0.25 e Å3
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.42822 (8)0.6551 (4)0.0621 (2)0.0519 (5)
O20.67592 (7)0.1566 (4)0.4609 (1)0.0500 (5)
O30.61383 (7)0.1929 (4)0.5347 (1)0.0539 (5)
N40.43206 (8)0.2244 (4)0.0733 (2)0.0456 (5)
C50.1854 (1)0.6130 (6)0.2582 (2)0.0469 (6)
C60.1942 (1)0.4245 (6)0.1840 (2)0.0459 (6)
C70.2423 (1)0.4186 (5)0.1235 (2)0.0404 (6)
C80.28253 (9)0.6035 (5)0.1365 (2)0.0349 (5)
C90.2724 (1)0.7964 (5)0.2101 (2)0.0440 (6)
C100.2243 (1)0.7998 (5)0.2711 (2)0.0489 (6)
C110.3344 (1)0.6020 (5)0.0747 (2)0.0375 (5)
C120.3553 (1)0.4147 (5)0.0169 (2)0.0385 (5)
C130.4084 (1)0.4435 (5)0.0432 (2)0.0374 (5)
C140.4841 (1)0.2087 (6)0.1330 (2)0.0525 (7)
C150.4771 (1)0.0830 (6)0.2386 (2)0.0516 (7)
C160.53078 (9)0.0195 (5)0.2959 (2)0.0409 (6)
C170.5645 (1)0.1684 (6)0.2576 (2)0.0446 (6)
C180.6133 (1)0.2338 (5)0.3106 (2)0.0422 (6)
C190.62896 (9)0.1088 (5)0.4026 (2)0.0377 (5)
C200.59536 (9)0.0827 (5)0.4425 (2)0.0374 (5)
C210.5469 (1)0.1451 (5)0.3887 (2)0.0408 (6)
C220.7096 (1)0.3586 (6)0.4246 (2)0.0495 (7)
C230.5813 (1)0.3872 (6)0.5787 (2)0.0523 (7)
H40.41400.06950.05490.0547*
H50.15260.61420.30050.0562*
H60.16700.29780.17420.0551*
H70.24790.28730.07260.0485*
H90.29870.92750.21860.0527*
H100.21820.93110.32180.0587*
H110.35540.75440.07670.0450*
H120.33610.25750.01350.0462*
H14A0.49800.37600.14380.0629*
H14B0.50920.11200.09360.0629*
H15A0.45690.19490.28180.0619*
H15B0.45710.07080.22790.0619*
H170.55420.25460.19410.0534*
H180.63580.36440.28330.0506*
H210.52430.27590.41560.0490*
H22A0.68950.51360.42420.0593*
H22B0.74090.37480.47030.0593*
H22C0.72090.32160.35500.0593*
H23A0.54620.32020.59370.0627*
H23B0.59850.44770.64210.0627*
H23C0.57730.52380.52980.0627*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.051 (1)0.040 (1)0.064 (1)0.0040 (8)0.0139 (9)0.0034 (9)
O20.0405 (9)0.062 (1)0.0468 (10)0.0141 (9)0.0136 (8)0.0122 (9)
O30.051 (1)0.065 (1)0.0446 (10)0.0138 (9)0.0140 (8)0.0208 (9)
N40.039 (1)0.040 (1)0.057 (1)0.0034 (9)0.0161 (10)0.005 (1)
C50.041 (1)0.056 (2)0.044 (1)0.010 (1)0.007 (1)0.005 (1)
C60.038 (1)0.053 (2)0.046 (1)0.001 (1)0.001 (1)0.001 (1)
C70.042 (1)0.043 (1)0.036 (1)0.002 (1)0.0010 (10)0.005 (1)
C80.040 (1)0.035 (1)0.029 (1)0.0042 (10)0.0002 (9)0.0034 (9)
C90.048 (1)0.039 (1)0.045 (1)0.000 (1)0.003 (1)0.003 (1)
C100.055 (2)0.048 (2)0.043 (1)0.007 (1)0.009 (1)0.008 (1)
C110.040 (1)0.037 (1)0.036 (1)0.001 (1)0.0021 (10)0.0034 (10)
C120.038 (1)0.037 (1)0.040 (1)0.003 (1)0.0032 (10)0.001 (1)
C130.039 (1)0.039 (1)0.034 (1)0.002 (1)0.0012 (10)0.0018 (10)
C140.036 (1)0.055 (2)0.066 (2)0.005 (1)0.014 (1)0.012 (1)
C150.034 (1)0.077 (2)0.043 (1)0.005 (1)0.007 (1)0.007 (1)
C160.033 (1)0.054 (2)0.035 (1)0.002 (1)0.0030 (10)0.001 (1)
C170.041 (1)0.056 (2)0.037 (1)0.004 (1)0.006 (1)0.009 (1)
C180.039 (1)0.047 (1)0.040 (1)0.002 (1)0.001 (1)0.007 (1)
C190.032 (1)0.044 (1)0.037 (1)0.0012 (10)0.0042 (9)0.001 (1)
C200.038 (1)0.041 (1)0.033 (1)0.001 (1)0.0038 (9)0.0037 (10)
C210.036 (1)0.049 (1)0.037 (1)0.007 (1)0.0008 (10)0.002 (1)
C220.040 (1)0.055 (2)0.053 (2)0.011 (1)0.006 (1)0.002 (1)
C230.058 (2)0.052 (2)0.046 (1)0.004 (1)0.002 (1)0.014 (1)
Geometric parameters (Å, º) top
O1—C131.231 (3)C12—H120.950
O2—C191.369 (3)C14—C151.505 (4)
O2—C221.426 (3)C14—H14A0.950
O3—C201.367 (3)C14—H14B0.950
O3—C231.417 (4)C15—C161.518 (3)
N4—C131.337 (3)C15—H15A0.950
N4—C141.461 (3)C15—H15B0.950
N4—H40.950C16—C171.382 (4)
C5—C61.376 (4)C16—C211.394 (3)
C5—C101.378 (4)C17—C181.393 (3)
C5—H50.950C17—H170.950
C6—C71.385 (3)C18—C191.382 (3)
C6—H60.950C18—H180.950
C7—C81.395 (3)C19—C201.401 (3)
C7—H70.950C20—C211.388 (3)
C8—C91.392 (3)C21—H210.950
C8—C111.470 (3)C22—H22A0.950
C9—C101.388 (4)C22—H22B0.950
C9—H90.950C22—H22C0.950
C10—H100.950C23—H23A0.950
C11—C121.319 (3)C23—H23B0.950
C11—H110.950C23—H23C0.950
C12—C131.492 (3)
C19—O2—C22116.5 (2)H14A—C14—H14B109.5
C20—O3—C23117.7 (2)C14—C15—C16113.6 (2)
C13—N4—C14123.9 (2)C14—C15—H15A108.4
C13—N4—H4118.0C14—C15—H15B108.4
C14—N4—H4118.0C16—C15—H15A108.4
C6—C5—C10119.8 (2)C16—C15—H15B108.4
C6—C5—H5120.1H15A—C15—H15B109.5
C10—C5—H5120.1C15—C16—C17120.4 (2)
C5—C6—C7120.4 (2)C15—C16—C21121.2 (2)
C5—C6—H6119.8C17—C16—C21118.4 (2)
C7—C6—H6119.8C16—C17—C18121.2 (2)
C6—C7—C8120.6 (2)C16—C17—H17119.4
C6—C7—H7119.7C18—C17—H17119.4
C8—C7—H7119.7C17—C18—C19120.1 (2)
C7—C8—C9118.1 (2)C17—C18—H18120.0
C7—C8—C11122.3 (2)C19—C18—H18119.9
C9—C8—C11119.6 (2)O2—C19—C18125.1 (2)
C8—C9—C10120.9 (2)O2—C19—C20115.4 (2)
C8—C9—H9119.6C18—C19—C20119.5 (2)
C10—C9—H9119.5O3—C20—C19115.3 (2)
C5—C10—C9120.0 (2)O3—C20—C21125.1 (2)
C5—C10—H10120.0C19—C20—C21119.6 (2)
C9—C10—H10120.0C16—C21—C20121.2 (2)
C8—C11—C12127.8 (2)C16—C21—H21119.4
C8—C11—H11116.1C20—C21—H21119.4
C12—C11—H11116.1O2—C22—H22A109.5
C11—C12—C13121.7 (2)O2—C22—H22B109.5
C11—C12—H12119.2O2—C22—H22C109.5
C13—C12—H12119.2H22A—C22—H22B109.5
O1—C13—N4123.7 (2)H22A—C22—H22C109.5
O1—C13—C12121.4 (2)H22B—C22—H22C109.5
N4—C13—C12114.9 (2)O3—C23—H23A109.5
N4—C14—C15111.3 (2)O3—C23—H23B109.5
N4—C14—H14A109.0O3—C23—H23C109.5
N4—C14—H14B109.0H23A—C23—H23B109.5
C15—C14—H14A109.0H23A—C23—H23C109.5
C15—C14—H14B109.0H23B—C23—H23C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.952.202.990 (3)140
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC19H21NO3
Mr311.38
Crystal system, space groupMonoclinic, P21/a
Temperature (K)250
a, b, c (Å)24.449 (2), 5.2431 (5), 12.6633 (9)
β (°) 91.714 (6)
V3)1622.6 (2)
Z4
Radiation typeCu Kα
µ (mm1)0.69
Crystal size (mm)0.75 × 0.15 × 0.05
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionIntegration
(Coppens et al., 1965)
Tmin, Tmax0.842, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
4079, 3176, 2641
Rint0.025
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.156, 1.26
No. of reflections3176
No. of parameters209
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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.

Selected bond lengths (Å) top
O1—C131.231 (3)C11—C121.319 (3)
N4—C131.337 (3)C12—C131.492 (3)
N4—C141.461 (3)C14—C151.505 (4)
C8—C111.470 (3)C15—C161.518 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.952.202.990 (3)140
Symmetry code: (i) x, y1, z.
 

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