
The previously unknown crystal structure of the biogenic compound tryptamine, in the form of a free base (C10H12N2), has been solved from X-ray powder diffraction data using simulated annealing followed by restrained Rietveld refinement [space group P212121, a = 12.28593 (6), b = 8.53351 (4), c = 8.49385 (4) Å, Z = 4, final reduced-χ2 = 5.255]. A restrained Rietveld refinement was carried out in which the global weight factor, f, of the stereochemical restraints was gradually lowered. The effect of the relaxation of restraints on the crystal structure and on χ2 was studied and a criterion for the final choice of f is reported. The crystal structure reported here shows efficient packing involving weak intermolecular hydrogen bonding and a herringbone-type packing pattern.
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102011370/bm0051sup1.cif |
![]() | Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768102011370/bm0051sup2.rtv |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108768102011370/bm0051sup3.hkl |
CCDC reference: 195802
Computing details top
(TRYPT_phase_1) top
Crystal data top
? | c = 8.49385 (4) Å |
Mr = ? | V = ? Å3 |
Orthorhombic, P212121 | Z = ? |
a = 12.28593 (6) Å | ? radiation, λ = ? Å |
b = 8.53351 (4) Å | ?, ? × ? × ? mm |
Crystal data top
? | c = 8.49385 (4) Å |
Mr = ? | V = ? Å3 |
Orthorhombic, P212121 | Z = ? |
a = 12.28593 (6) Å | ? radiation, λ = ? Å |
b = 8.53351 (4) Å | ?, ? × ? × ? mm |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.2030 (4) | 0.8790 (7) | 1.0953 (5) | 0.0464 (7)* | |
C2 | 0.3076 (4) | 0.9420 (6) | 1.0836 (5) | 0.0464 (7)* | |
C3 | 0.3748 (4) | 0.9048 (7) | 0.9605 (6) | 0.0464 (7)* | |
C4 | 0.1659 (4) | 0.7708 (6) | 0.9885 (6) | 0.0464 (7)* | |
C5 | 0.2333 (3) | 0.7249 (6) | 0.8653 (5) | 0.0464 (7)* | |
C6 | 0.3376 (3) | 0.7930 (6) | 0.8526 (5) | 0.0464 (7)* | |
N7 | 0.3864 (3) | 0.7303 (5) | 0.7217 (5) | 0.0507 (14)* | |
C8 | 0.3178 (4) | 0.6250 (7) | 0.6542 (5) | 0.0464 (7)* | |
C9 | 0.2223 (3) | 0.6177 (6) | 0.7353 (5) | 0.0464 (7)* | |
H10 | 0.4567 (13) | 0.728 (3) | 0.708 (3) | 0.025* | |
C11 | 0.1234 (4) | 0.5241 (5) | 0.6943 (6) | 0.0464 (7)* | |
C12 | 0.0430 (4) | 0.6098 (7) | 0.5890 (6) | 0.0464 (7)* | |
N13 | 0.0819 (4) | 0.6579 (6) | 0.4376 (6) | 0.0507 (14)* | |
H14 | 0.4495 (16) | 0.943 (4) | 0.957 (3) | 0.025* | |
H15 | 0.3254 (15) | 1.033 (3) | 1.143 (3) | 0.025* | |
H16 | 0.1661 (17) | 0.885 (3) | 1.195 (2) | 0.025* | |
H17 | 0.3334 (17) | 0.581 (4) | 0.553 (3) | 0.025* | |
H18 | 0.1453 (11) | 0.4220 (19) | 0.647 (2) | 0.025* | |
H19 | 0.0863 (11) | 0.4921 (19) | 0.7917 (18) | 0.025* | |
H20 | 0.0922 (18) | 0.726 (4) | 0.998 (3) | 0.025* | |
H21 | −0.0196 (13) | 0.540 (2) | 0.5740 (17) | 0.025* | |
H22 | 0.0158 (18) | 0.7059 (18) | 0.6429 (18) | 0.025* | |
H23 | 0.108 (3) | 0.574 (2) | 0.378 (3) | 0.025* | |
H24 | 0.126 (3) | 0.748 (3) | 0.432 (3) | 0.025* |
Experimental details
Crystal data | |
Chemical formula | ? |
Mr | ? |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | ? |
a, b, c (Å) | 12.28593 (6), 8.53351 (4), 8.49385 (4) |
V (Å3) | ? |
Z | ? |
Radiation type | ?, λ = ? Å |
Specimen shape, size (mm) | ?, ? × ? × ? |
Data collection | |
Diffractometer | ? |
Specimen mounting | ? |
Data collection mode | ? |
Scan method | ? |
2θ values (°) | 2θmin = ? 2θmax = ? 2θstep = ? |
Refinement | |
R factors and goodness of fit | Rp = ?, Rwp = ?, Rexp = ?, χ2 = NOT FOUND |
No. of data points | ? |
No. of parameters | ? |
No. of restraints | ? |