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The experimental charge density ρ(r) of the non-standard amino acid sarcosine has been determined based on an extensive and complete data set measured at 100 K to high resolution (sin θ/λ = 1.18 Å−1) by single-crystal X-ray diffraction. Anisotropic thermal motion of the H atoms, obtained from TLS + ONIOM cluster methods, was included in the structural model. Based on the multipole-model geometry, the theoretical Hartree–Fock interaction density of a molecule in the crystal has been calculated with CRYSTAL98. It manifests itself in local rearrangements of ρ(r) and can be reproduced with a multipole projection via simulated structure factors. An attempt has also been made to obtain the interaction density from a combination of experimental and theoretical charge densities using either a whole-molecular calculation or the invariom database. Agreement with the periodic Hartree–Fock interaction density is qualitative. It is shown that invarioms reproduce the features of the theoretical multipole-projected whole-molecular electron density, and can be used to approximate it.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108767307039116/sh5061sup1.cif
Contains datablock sarcosine

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108767307039116/sh5061sup2.hkl
Contains datablock SAR

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108767307039116/sh5061sup3.pdf
Figure showing static deformation density plot

CCDC reference: 660888

Computing details top

Program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(sarcosine) top
Crystal data top
C3H7NO2F(000) = 192.0
Mr = 89.10Dx = 1.309 Mg m3
Orthorhombic, P212121? radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 48765 reflections
a = 6.6558 (1) Åθ = 3.1–57.2°
b = 7.8903 (1) ŵ = 0.11 mm1
c = 8.6069 (1) ÅT = 100 K
V = 452.01 (1) Å3Tetrahedron, colorless
Z = 4.00.48 × 0.39 × 0.32 mm
Data collection top
Oxford Diffraction Xcalibur S
diffractometer
2927 reflections with F > 2.5u(σ)F
ω scansRint = 0.027
Absorption correction: analytical
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
θmax = 57.8°, θmin = 3.1°
Tmin = 0.969, Tmax = 0.977h = 1515
78770 measured reflectionsk = 1818
3555 independent reflectionsl = 2020
Refinement top
Refinement on F0 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.017 w1 = 1/[s2(Fo)]
wR(F2) = 0.010(Δ/σ)max < 0.001
S = 1.71Δρmax = 0.17 e Å3
2927 reflectionsΔρmin = 0.16 e Å3
156 parameters
Crystal data top
C3H7NO2V = 452.01 (1) Å3
Mr = 89.10Z = 4.0
Orthorhombic, P212121? radiation, λ = 0.71073 Å
a = 6.6558 (1) ŵ = 0.11 mm1
b = 7.8903 (1) ÅT = 100 K
c = 8.6069 (1) Å0.48 × 0.39 × 0.32 mm
Data collection top
Oxford Diffraction Xcalibur S
diffractometer
3555 independent reflections
Absorption correction: analytical
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
2927 reflections with F > 2.5u(σ)F
Tmin = 0.969, Tmax = 0.977Rint = 0.027
78770 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0170 restraints
wR(F2) = 0.010All H-atom parameters refined
S = 1.71Δρmax = 0.17 e Å3
2927 reflectionsΔρmin = 0.16 e Å3
156 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O(1)0.77985 (3)0.18119 (2)0.17238 (2)0.014
O(2)0.76653 (3)0.09296 (2)0.23721 (2)0.018
N(1)1.01610 (3)0.06195 (2)0.47965 (2)0.01
C(1)0.82272 (3)0.05492 (3)0.25761 (2)0.011
C(2)0.95498 (3)0.09441 (3)0.39760 (2)0.011
C(3)1.18181 (4)0.03359 (3)0.59155 (3)0.017
H(1)1.0576 (7)0.1511 (6)0.4049 (6)0.024
H(2)0.8981 (8)0.1059 (6)0.5387 (6)0.033
H(3)1.0843 (8)0.1638 (6)0.3583 (6)0.032
H(4)0.8722 (8)0.1719 (6)0.4761 (6)0.031
H(5)1.3186 (8)0.0054 (7)0.5326 (7)0.042
H(6)1.2092 (8)0.1506 (7)0.6522 (6)0.037
H(7)1.1388 (8)0.0621 (8)0.6749 (7)0.045
DUM11.080060.050940.4978500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.01736 (7)0.01148 (6)0.01315 (6)0.00181 (6)0.00362 (6)0.00387 (5)
O(2)0.02510 (9)0.00983 (5)0.01828 (8)0.00150 (6)0.00887 (7)0.00061 (6)
N(1)0.01281 (7)0.00894 (6)0.00962 (6)0.00028 (5)0.00115 (5)0.00007 (5)
C(1)0.01345 (7)0.00932 (6)0.01003 (7)0.00016 (6)0.00089 (6)0.00104 (6)
C(2)0.01473 (8)0.00944 (7)0.00987 (7)0.00042 (6)0.00099 (6)0.00017 (6)
C(3)0.01940 (10)0.01370 (10)0.01760 (10)0.00030 (10)0.00720 (10)0.00010 (10)
H(1)0.028 (2)0.020.0250.00700.006
H(2)0.040 (3)0.020.0390.0030.0080.005
H(3)0.035 (3)0.0290.0320.0070.0040.013
H(4)0.048 (3)0.0220.0230.01100.004
H(5)0.021 (3)0.0510.0540.0160.0030.001
H(6)0.037 (3)0.0330.040.0070.0180.012
H(7)0.051 (3)0.0460.0380.0150.0180.025
Geometric parameters (Å, º) top
O(1)—C(1)1.2697 (3)C(2)—H(3)1.075 (5)
O(2)—C(1)1.2378 (3)C(2)—H(4)1.065 (5)
N(1)—H(1)0.993 (5)C(3)—H(5)1.087 (5)
N(1)—H(2)0.997 (5)C(3)—H(6)1.077 (5)
C(1)—C(2)1.5244 (3)C(3)—H(7)1.080 (6)
H(1)—N(1)—H(2)107.6 (4)C(1)—C(2)—H(4)108.7 (3)
O(1)—C(1)—O(2)126.14 (2)H(3)—C(2)—H(4)108.8 (4)
O(1)—C(1)—C(2)115.215 (18)H(5)—C(3)—H(6)109.1 (4)
O(2)—C(1)—C(2)118.640 (19)H(5)—C(3)—H(7)109.5 (4)
C(1)—C(2)—H(3)108.5 (3)H(6)—C(3)—H(7)108.8 (4)

Experimental details

Crystal data
Chemical formulaC3H7NO2
Mr89.10
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)6.6558 (1), 7.8903 (1), 8.6069 (1)
V3)452.01 (1)
Z4.0
Radiation type?, λ = 0.71073 Å
µ (mm1)0.11
Crystal size (mm)0.48 × 0.39 × 0.32
Data collection
DiffractometerOxford Diffraction Xcalibur S
diffractometer
Absorption correctionAnalytical
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Tmin, Tmax0.969, 0.977
No. of measured, independent and
observed [F > 2.5u(σ)F] reflections
78770, 3555, 2927
Rint0.027
(sin θ/λ)max1)1.190
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.017, 0.010, 1.71
No. of reflections2927
No. of parameters156
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.17, 0.16

Computer programs: Koritsanszky et al., (2003).

Selected geometric parameters (Å, º) top
O(1)—C(1)1.2697 (3)C(2)—H(3)1.075 (5)
O(2)—C(1)1.2378 (3)C(2)—H(4)1.065 (5)
N(1)—H(1)0.993 (5)C(3)—H(5)1.087 (5)
N(1)—H(2)0.997 (5)C(3)—H(6)1.077 (5)
C(1)—C(2)1.5244 (3)C(3)—H(7)1.080 (6)
H(1)—N(1)—H(2)107.6 (4)C(1)—C(2)—H(4)108.7 (3)
O(1)—C(1)—O(2)126.14 (2)H(3)—C(2)—H(4)108.8 (4)
O(1)—C(1)—C(2)115.215 (18)H(5)—C(3)—H(6)109.1 (4)
O(2)—C(1)—C(2)118.640 (19)H(5)—C(3)—H(7)109.5 (4)
C(1)—C(2)—H(3)108.5 (3)H(6)—C(3)—H(7)108.8 (4)
 

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