Three X-ray data sets of the same D,L-serine crystal were measured at temperatures of 298, 100 and 20 K. These data were then evaluated using invarioms and the Hansen & Coppens aspherical-atom model. Multipole populations for invarioms, which are pseudoatoms that remain approximately invariant in an intermolecular transfer, were theoretically predicted using different density functional theorem (DFT) basis sets. The invariom parameters were kept fixed and positional and thermal parameters were refined to compare the fitting against the multi-temperature data at different resolutions. The deconvolution of thermal motion and electron density with respect to data resolution was studied by application of the Hirshfeld test. Above a resolution of sinθ/λ ≈ 0.55 Å−1, or d ≈ 0.9 Å, this test was fulfilled. When the Hirshfeld test is fulfilled, a successful modeling of the aspherical electron density with invarioms is achieved, which was proven by Fourier methods. Molecular geometry improves, especially for H atoms, when using the invariom method compared to the independent-atom model, as a comparison with neutron data shows. Based on this example, the general applicability of the invariom concept to organic molecules is proven and the aspherical density modeling of a larger biomacromolecule is within reach.
Supporting information
CCDC references: 273584; 273585; 273586
For all compounds, program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003), PLATON (Spek, 2003); software used to prepare material for publication: Koritsanszky et al., (2003), enCIFer 1.1.
(298K) (±) 2-Amino-3-hydroxypropionic acid
top
Crystal data top
C3H7NO3 | F(000) = 224.0 |
Mr = 105.10 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/a | Melting point: 235 K |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7355 (9) Å | Cell parameters from 13549 reflections |
b = 9.1456 (7) Å | θ = 3.0–43.3° |
c = 4.8304 (4) Å | µ = 0.14 mm−1 |
β = 106.46 (1)° | T = 298 K |
V = 454.83 (7) Å3 | Rectangular, colorless |
Z = 4 | 0.5 × 0.45 × 0.35 mm |
Data collection top
Bruker APEX on a Huber Type 512 diffractometer | Rint = 0.023 |
Graphite monochromator | θmax = 44.4° |
ω–scans | h = −9→4 |
25178 measured reflections | k = −17→17 |
3551 independent reflections | l = −20→20 |
2703 reflections with I > 2σ I | |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.022 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.026 | (Δ/σ)max < 0.001 |
S = 1.39 | Δρmax = 0.20 e Å−3 |
2703 reflections | Δρmin = −0.21 e Å−3 |
93 parameters | |
Crystal data top
C3H7NO3 | V = 454.83 (7) Å3 |
Mr = 105.10 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 10.7355 (9) Å | µ = 0.14 mm−1 |
b = 9.1456 (7) Å | T = 298 K |
c = 4.8304 (4) Å | 0.5 × 0.45 × 0.35 mm |
β = 106.46 (1)° | |
Data collection top
Bruker APEX on a Huber Type 512 diffractometer | 2703 reflections with I > 2σ I |
25178 measured reflections | Rint = 0.023 |
3551 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.026 | All H-atom parameters refined |
S = 1.39 | Δρmax = 0.20 e Å−3 |
2703 reflections | Δρmin = −0.21 e Å−3 |
93 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O(1) | 0.66393 (3) | 0.40214 (4) | 0.43070 (6) | 0.03 | |
O(2) | 0.83195 (4) | 0.50585 (4) | 0.75250 (7) | 0.033 | |
O(3) | 0.93151 (3) | 0.16868 (4) | 0.72969 (8) | 0.034 | |
N(1) | 0.65241 (3) | 0.16997 (4) | 0.74433 (7) | 0.023 | |
C(1) | 0.74963 (4) | 0.40565 (4) | 0.66748 (7) | 0.023 | |
C(2) | 0.75489 (3) | 0.27886 (4) | 0.87766 (7) | 0.022 | |
C(3) | 0.88895 (4) | 0.20938 (5) | 0.97056 (8) | 0.027 | |
H(2) | 0.7320 (7) | 0.3221 (8) | 1.0656 (16) | 0.035 (2) | |
H(11) | 0.5640 (9) | 0.2268 (10) | 0.6878 (17) | 0.048 (2) | |
H(12) | 0.6497 (8) | 0.0921 (11) | 0.898 (2) | 0.051 (2) | |
H(13) | 0.6653 (9) | 0.1174 (10) | 0.566 (2) | 0.049 (2) | |
H(31) | 0.9576 (8) | 0.2904 (10) | 1.0945 (17) | 0.046 (2) | |
H(32) | 0.8885 (8) | 0.1141 (10) | 1.1162 (19) | 0.053 (2) | |
H(4) | 0.9032 (8) | 0.0721 (11) | 0.6743 (19) | 0.043 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(1) | 0.0380 (2) | 0.02510 (10) | 0.02340 (10) | −0.00120 (10) | 0.00300 (10) | 0.00480 (10) |
O(2) | 0.0428 (2) | 0.02440 (10) | 0.02840 (10) | −0.00950 (10) | 0.00940 (10) | −0.00210 (10) |
O(3) | 0.02540 (10) | 0.03010 (10) | 0.0445 (2) | −0.00570 (10) | 0.01710 (10) | −0.01010 (10) |
N(1) | 0.02190 (10) | 0.02110 (10) | 0.02500 (10) | 0.00180 (10) | 0.00820 (10) | 0.00360 (10) |
C(1) | 0.0286 (2) | 0.01860 (10) | 0.01990 (10) | −0.00010 (10) | 0.00880 (10) | −0.00070 (10) |
C(2) | 0.02430 (10) | 0.02140 (10) | 0.01800 (10) | 0.00150 (10) | 0.00810 (10) | 0.00060 (10) |
C(3) | 0.02250 (10) | 0.0294 (2) | 0.02650 (10) | 0.00160 (10) | 0.00410 (10) | 0.00130 (10) |
Geometric parameters (Å, º) top
O(1)—C(1) | 1.2487 (5) | N(1)—H(13) | 1.030 (10) |
O(2)—C(1) | 1.2585 (5) | C(1)—C(2) | 1.5316 (5) |
O(3)—C(3) | 1.4150 (5) | C(2)—C(3) | 1.5201 (5) |
O(3)—H(4) | 0.947 (10) | C(2)—H(2) | 1.080 (7) |
N(1)—C(2) | 1.4884 (5) | C(3)—H(31) | 1.096 (9) |
N(1)—H(11) | 1.048 (9) | C(3)—H(32) | 1.121 (9) |
N(1)—H(12) | 1.034 (10) | | |
| | | |
C(3)—O(3)—H(4) | 109.0 (5) | N(1)—C(2)—C(3) | 111.71 (3) |
C(2)—N(1)—H(11) | 106.5 (5) | N(1)—C(2)—H(2) | 107.0 (4) |
C(2)—N(1)—H(12) | 108.6 (5) | C(1)—C(2)—C(3) | 111.48 (3) |
C(2)—N(1)—H(13) | 114.6 (5) | C(1)—C(2)—H(2) | 107.8 (4) |
H(11)—N(1)—H(12) | 108.7 (6) | C(3)—C(2)—H(2) | 109.1 (4) |
H(11)—N(1)—H(13) | 109.9 (6) | O(3)—C(3)—C(2) | 111.50 (3) |
H(12)—N(1)—H(13) | 108.4 (6) | O(3)—C(3)—H(31) | 107.6 (4) |
O(1)—C(1)—O(2) | 125.77 (4) | O(3)—C(3)—H(32) | 111.8 (4) |
O(1)—C(1)—C(2) | 117.84 (3) | C(2)—C(3)—H(31) | 108.2 (4) |
O(2)—C(1)—C(2) | 116.38 (3) | C(2)—C(3)—H(32) | 109.8 (4) |
N(1)—C(2)—C(1) | 109.62 (3) | H(31)—C(3)—H(32) | 107.7 (6) |
(100K) (±) 2-Amino-3-hydroxypropionic acid
top
Crystal data top
C3H7NO3 | F(000) = 224.0 |
Mr = 105.10 | Dx = 1.542 Mg m−3 |
Monoclinic, P21/a | Melting point: 235 K |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7621 (10) Å | Cell parameters from 9829 reflections |
b = 9.1771 (9) Å | θ = 16.2–40.2° |
c = 4.7883 (5) Å | µ = 0.14 mm−1 |
β = 106.76 (2)° | T = 100 K |
V = 452.83 (9) Å3 | Rectangular, colorless |
Z = 4 | 0.5 × 0.45 × 0.35 mm |
Data collection top
Bruker APEX on a Huber Type 512 diffractometer | Rint = 0.029 |
Graphite monochromator | θmax = 57.6° |
ω–scans | h = −4→8 |
38455 measured reflections | k = −21→21 |
5146 independent reflections | l = −24→24 |
4109 reflections with I > 2σ I | |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.023 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.024 | (Δ/σ)max < 0.001 |
S = 1.24 | Δρmax = 0.23 e Å−3 |
4109 reflections | Δρmin = −0.22 e Å−3 |
93 parameters | |
Crystal data top
C3H7NO3 | V = 452.83 (9) Å3 |
Mr = 105.10 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 10.7621 (10) Å | µ = 0.14 mm−1 |
b = 9.1771 (9) Å | T = 100 K |
c = 4.7883 (5) Å | 0.5 × 0.45 × 0.35 mm |
β = 106.76 (2)° | |
Data collection top
Bruker APEX on a Huber Type 512 diffractometer | 4109 reflections with I > 2σ I |
38455 measured reflections | Rint = 0.029 |
5146 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.023 | 0 restraints |
wR(F2) = 0.024 | All H-atom parameters refined |
S = 1.24 | Δρmax = 0.23 e Å−3 |
4109 reflections | Δρmin = −0.22 e Å−3 |
93 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O(1) | 0.65971 (2) | 0.40588 (2) | 0.42808 (5) | 0.012 | |
O(2) | 0.82960 (2) | 0.50982 (2) | 0.75169 (5) | 0.013 | |
O(3) | 0.92941 (2) | 0.17379 (2) | 0.72353 (5) | 0.014 | |
N(1) | 0.65294 (2) | 0.17254 (2) | 0.74409 (5) | 0.01 | |
C(1) | 0.74714 (2) | 0.40934 (2) | 0.66646 (5) | 0.01 | |
C(2) | 0.75448 (2) | 0.28247 (3) | 0.87869 (5) | 0.009 | |
C(3) | 0.88934 (2) | 0.21473 (3) | 0.97025 (6) | 0.011 | |
H(2) | 0.7325 (7) | 0.3234 (8) | 1.0664 (16) | 0.020 (2) | |
H(11) | 0.5643 (9) | 0.2289 (10) | 0.6837 (17) | 0.030 (2) | |
H(12) | 0.6531 (9) | 0.0944 (11) | 0.904 (2) | 0.037 (2) | |
H(13) | 0.6664 (9) | 0.1217 (10) | 0.561 (2) | 0.035 (2) | |
H(31) | 0.9566 (8) | 0.2970 (9) | 1.0920 (16) | 0.025 (2) | |
H(32) | 0.8894 (8) | 0.1195 (10) | 1.1160 (16) | 0.027 (2) | |
H(4) | 0.9019 (8) | 0.0771 (10) | 0.6736 (17) | 0.025 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(1) | 0.01460 (6) | 0.01086 (6) | 0.00987 (7) | −0.00053 (5) | 0.00144 (5) | 0.00166 (5) |
O(2) | 0.01635 (7) | 0.01052 (6) | 0.01157 (8) | −0.00359 (5) | 0.00396 (6) | −0.00086 (5) |
O(3) | 0.01123 (6) | 0.01288 (6) | 0.01697 (9) | −0.00212 (5) | 0.00720 (6) | −0.00381 (6) |
N(1) | 0.00949 (5) | 0.00947 (6) | 0.01064 (8) | 0.00049 (4) | 0.00363 (5) | 0.00128 (5) |
C(1) | 0.01157 (7) | 0.00838 (6) | 0.00847 (8) | −0.00019 (5) | 0.00359 (5) | −0.00024 (5) |
C(2) | 0.01012 (6) | 0.00950 (6) | 0.00812 (8) | 0.00061 (5) | 0.00350 (5) | 0.00035 (5) |
C(3) | 0.00958 (6) | 0.01267 (7) | 0.01108 (9) | 0.00070 (6) | 0.00229 (6) | 0.00030 (6) |
Geometric parameters (Å, º) top
O(1)—C(1) | 1.2529 (3) | N(1)—H(13) | 1.039 (10) |
O(2)—C(1) | 1.2632 (3) | C(1)—C(2) | 1.5323 (3) |
O(3)—C(3) | 1.4201 (3) | C(2)—C(3) | 1.5226 (3) |
O(3)—H(4) | 0.944 (10) | C(2)—H(2) | 1.062 (7) |
N(1)—H(11) | 1.050 (9) | C(3)—H(31) | 1.091 (8) |
N(1)—H(12) | 1.048 (10) | C(3)—H(32) | 1.118 (9) |
| | | |
C(3)—O(3)—H(4) | 108.1 (5) | C(1)—C(2)—H(2) | 108.1 (4) |
H(11)—N(1)—H(12) | 110.4 (6) | C(3)—C(2)—H(2) | 109.1 (4) |
H(11)—N(1)—H(13) | 109.0 (6) | O(3)—C(3)—C(2) | 111.19 (2) |
H(12)—N(1)—H(13) | 109.7 (7) | O(3)—C(3)—H(31) | 108.3 (4) |
O(1)—C(1)—O(2) | 125.86 (2) | O(3)—C(3)—H(32) | 111.5 (4) |
O(1)—C(1)—C(2) | 117.81 (2) | C(2)—C(3)—H(31) | 107.5 (4) |
O(2)—C(1)—C(2) | 116.32 (2) | C(2)—C(3)—H(32) | 109.1 (4) |
C(1)—C(2)—C(3) | 111.329 (19) | H(31)—C(3)—H(32) | 109.1 (5) |
(20K) (±) 2-Amino-3-hydroxypropionic acid
top
Crystal data top
C3H7NO3 | F(000) = 224.0 |
Mr = 105.10 | Dx = 1.541 Mg m−3 |
Monoclinic, P21/a | Melting point: 235 K |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7764 (10) Å | Cell parameters from 10633 reflections |
b = 9.1947 (9) Å | θ = 16.4–40.3° |
c = 4.7788 (5) Å | µ = 0.14 mm−1 |
β = 106.87 (2)° | T = 20 K |
V = 453.13 (9) Å3 | Rectangular, colorless |
Z = 4 | 0.5 × 0.45 × 0.35 mm |
Data collection top
Bruker APEX on a Huber Type 512 diffractometer | Rint = 0.027 |
Graphite monochromator | θmax = 57.4° |
ω–scans | h = −4→8 |
38628 measured reflections | k = −21→21 |
5136 independent reflections | l = −24→24 |
4292 reflections with I > 2σ I | |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.020 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.022 | (Δ/σ)max < 0.001 |
S = 1.30 | Δρmax = 0.22 e Å−3 |
4292 reflections | Δρmin = −0.24 e Å−3 |
93 parameters | |
Crystal data top
C3H7NO3 | V = 453.13 (9) Å3 |
Mr = 105.10 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 10.7764 (10) Å | µ = 0.14 mm−1 |
b = 9.1947 (9) Å | T = 20 K |
c = 4.7788 (5) Å | 0.5 × 0.45 × 0.35 mm |
β = 106.87 (2)° | |
Data collection top
Bruker APEX on a Huber Type 512 diffractometer | 4292 reflections with I > 2σ I |
38628 measured reflections | Rint = 0.027 |
5136 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.020 | 0 restraints |
wR(F2) = 0.022 | All H-atom parameters refined |
S = 1.30 | Δρmax = 0.22 e Å−3 |
4292 reflections | Δρmin = −0.24 e Å−3 |
93 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O(1) | 0.65863 (2) | 0.40703 (2) | 0.42739 (4) | 0.008 | |
O(2) | 0.82879 (2) | 0.51099 (2) | 0.75170 (4) | 0.008 | |
O(3) | 0.92877 (2) | 0.17538 (2) | 0.72150 (4) | 0.009 | |
N(1) | 0.65325 (2) | 0.17344 (2) | 0.74378 (4) | 0.007 | |
C(1) | 0.74647 (2) | 0.41044 (2) | 0.66619 (5) | 0.006 | |
C(2) | 0.75445 (2) | 0.28355 (2) | 0.87889 (5) | 0.006 | |
C(3) | 0.88949 (2) | 0.21634 (2) | 0.96983 (5) | 0.007 | |
H(2) | 0.7323 (7) | 0.3266 (8) | 1.0683 (15) | 0.017 (2) | |
H(11) | 0.5631 (9) | 0.2275 (10) | 0.6859 (16) | 0.027 (2) | |
H(12) | 0.6515 (8) | 0.0966 (10) | 0.8979 (19) | 0.029 (2) | |
H(13) | 0.6661 (8) | 0.1228 (9) | 0.5615 (18) | 0.027 (2) | |
H(31) | 0.9586 (7) | 0.2992 (8) | 1.0924 (15) | 0.019 (2) | |
H(32) | 0.8924 (7) | 0.1206 (9) | 1.1175 (16) | 0.021 (2) | |
H(4) | 0.9045 (7) | 0.0799 (9) | 0.6731 (16) | 0.019 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(1) | 0.00876 (5) | 0.00731 (5) | 0.00610 (6) | −0.00043 (4) | 0.00064 (4) | 0.00097 (4) |
O(2) | 0.00950 (5) | 0.00679 (5) | 0.00720 (6) | −0.00213 (4) | 0.00222 (4) | −0.00038 (4) |
O(3) | 0.00763 (5) | 0.00849 (5) | 0.00943 (6) | −0.00099 (4) | 0.00436 (4) | −0.00187 (4) |
N(1) | 0.00635 (5) | 0.00634 (5) | 0.00684 (6) | −0.00015 (4) | 0.00228 (4) | 0.00060 (4) |
C(1) | 0.00683 (5) | 0.00548 (5) | 0.00525 (7) | −0.00021 (4) | 0.00200 (4) | −0.00002 (4) |
C(2) | 0.00638 (5) | 0.00603 (5) | 0.00531 (7) | 0.00023 (4) | 0.00217 (4) | 0.00030 (4) |
C(3) | 0.00619 (5) | 0.00815 (6) | 0.00659 (7) | 0.00060 (4) | 0.00152 (4) | 0.00026 (5) |
Geometric parameters (Å, º) top
O(1)—C(1) | 1.2539 (3) | N(1)—H(13) | 1.032 (9) |
O(2)—C(1) | 1.2643 (3) | C(1)—C(2) | 1.5333 (3) |
O(3)—C(3) | 1.4216 (3) | C(2)—C(3) | 1.5236 (3) |
O(3)—H(4) | 0.926 (9) | C(2)—H(2) | 1.076 (7) |
N(1)—H(11) | 1.054 (9) | C(3)—H(31) | 1.107 (8) |
N(1)—H(12) | 1.025 (9) | C(3)—H(32) | 1.123 (8) |
| | | |
C(3)—O(3)—H(4) | 109.2 (4) | C(1)—C(2)—H(2) | 107.1 (4) |
H(11)—N(1)—H(12) | 107.8 (6) | C(3)—C(2)—H(2) | 109.6 (4) |
H(11)—N(1)—H(13) | 109.3 (6) | O(3)—C(3)—C(2) | 111.129 (17) |
H(12)—N(1)—H(13) | 109.3 (6) | O(3)—C(3)—H(31) | 107.9 (3) |
O(1)—C(1)—O(2) | 125.88 (2) | O(3)—C(3)—H(32) | 110.9 (4) |
O(1)—C(1)—C(2) | 117.815 (18) | C(2)—C(3)—H(31) | 108.2 (4) |
O(2)—C(1)—C(2) | 116.298 (18) | C(2)—C(3)—H(32) | 110.3 (4) |
C(1)—C(2)—C(3) | 111.284 (16) | H(31)—C(3)—H(32) | 108.4 (5) |
Experimental details
| (298K) | (100K) | (20K) |
Crystal data |
Chemical formula | C3H7NO3 | C3H7NO3 | C3H7NO3 |
Mr | 105.10 | 105.10 | 105.10 |
Crystal system, space group | Monoclinic, P21/a | Monoclinic, P21/a | Monoclinic, P21/a |
Temperature (K) | 298 | 100 | 20 |
a, b, c (Å) | 10.7355 (9), 9.1456 (7), 4.8304 (4) | 10.7621 (10), 9.1771 (9), 4.7883 (5) | 10.7764 (10), 9.1947 (9), 4.7788 (5) |
β (°) | 106.46 (1) | 106.76 (2) | 106.87 (2) |
V (Å3) | 454.83 (7) | 452.83 (9) | 453.13 (9) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.14 | 0.14 |
Crystal size (mm) | 0.5 × 0.45 × 0.35 | 0.5 × 0.45 × 0.35 | 0.5 × 0.45 × 0.35 |
|
Data collection |
Diffractometer | Bruker APEX on a Huber Type 512 diffractometer | Bruker APEX on a Huber Type 512 diffractometer | Bruker APEX on a Huber Type 512 diffractometer |
Absorption correction | – | – | – |
No. of measured, independent and observed (I > 2σ I) reflections | 25178, 3551, 2703 | 38455, 5146, 4109 | 38628, 5136, 4292 |
Rint | 0.023 | 0.029 | 0.027 |
(sin θ/λ)max (Å−1) | 0.985 | 1.188 | 1.185 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.026, 1.39 | 0.023, 0.024, 1.24 | 0.020, 0.022, 1.30 |
No. of reflections | 2703 | 4109 | 4292 |
No. of parameters | 93 | 93 | 93 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.20, −0.21 | 0.23, −0.22 | 0.22, −0.24 |
Selected geometric parameters (Å, º) for (298K) topO(1)—C(1) | 1.2487 (5) | N(1)—H(13) | 1.030 (10) |
O(2)—C(1) | 1.2585 (5) | C(1)—C(2) | 1.5316 (5) |
O(3)—C(3) | 1.4150 (5) | C(2)—C(3) | 1.5201 (5) |
O(3)—H(4) | 0.947 (10) | C(2)—H(2) | 1.080 (7) |
N(1)—C(2) | 1.4884 (5) | C(3)—H(31) | 1.096 (9) |
N(1)—H(11) | 1.048 (9) | C(3)—H(32) | 1.121 (9) |
N(1)—H(12) | 1.034 (10) | | |
| | | |
C(3)—O(3)—H(4) | 109.0 (5) | N(1)—C(2)—C(3) | 111.71 (3) |
C(2)—N(1)—H(11) | 106.5 (5) | N(1)—C(2)—H(2) | 107.0 (4) |
C(2)—N(1)—H(12) | 108.6 (5) | C(1)—C(2)—C(3) | 111.48 (3) |
C(2)—N(1)—H(13) | 114.6 (5) | C(1)—C(2)—H(2) | 107.8 (4) |
H(11)—N(1)—H(12) | 108.7 (6) | C(3)—C(2)—H(2) | 109.1 (4) |
H(11)—N(1)—H(13) | 109.9 (6) | O(3)—C(3)—C(2) | 111.50 (3) |
H(12)—N(1)—H(13) | 108.4 (6) | O(3)—C(3)—H(31) | 107.6 (4) |
O(1)—C(1)—O(2) | 125.77 (4) | O(3)—C(3)—H(32) | 111.8 (4) |
O(1)—C(1)—C(2) | 117.84 (3) | C(2)—C(3)—H(31) | 108.2 (4) |
O(2)—C(1)—C(2) | 116.38 (3) | C(2)—C(3)—H(32) | 109.8 (4) |
N(1)—C(2)—C(1) | 109.62 (3) | H(31)—C(3)—H(32) | 107.7 (6) |
Selected geometric parameters (Å, º) for (100K) topO(1)—C(1) | 1.2529 (3) | N(1)—H(13) | 1.039 (10) |
O(2)—C(1) | 1.2632 (3) | C(1)—C(2) | 1.5323 (3) |
O(3)—C(3) | 1.4201 (3) | C(2)—C(3) | 1.5226 (3) |
O(3)—H(4) | 0.944 (10) | C(2)—H(2) | 1.062 (7) |
N(1)—H(11) | 1.050 (9) | C(3)—H(31) | 1.091 (8) |
N(1)—H(12) | 1.048 (10) | C(3)—H(32) | 1.118 (9) |
| | | |
C(3)—O(3)—H(4) | 108.1 (5) | C(1)—C(2)—H(2) | 108.1 (4) |
H(11)—N(1)—H(12) | 110.4 (6) | C(3)—C(2)—H(2) | 109.1 (4) |
H(11)—N(1)—H(13) | 109.0 (6) | O(3)—C(3)—C(2) | 111.19 (2) |
H(12)—N(1)—H(13) | 109.7 (7) | O(3)—C(3)—H(31) | 108.3 (4) |
O(1)—C(1)—O(2) | 125.86 (2) | O(3)—C(3)—H(32) | 111.5 (4) |
O(1)—C(1)—C(2) | 117.81 (2) | C(2)—C(3)—H(31) | 107.5 (4) |
O(2)—C(1)—C(2) | 116.32 (2) | C(2)—C(3)—H(32) | 109.1 (4) |
C(1)—C(2)—C(3) | 111.329 (19) | H(31)—C(3)—H(32) | 109.1 (5) |
Selected geometric parameters (Å, º) for (20K) topO(1)—C(1) | 1.2539 (3) | N(1)—H(13) | 1.032 (9) |
O(2)—C(1) | 1.2643 (3) | C(1)—C(2) | 1.5333 (3) |
O(3)—C(3) | 1.4216 (3) | C(2)—C(3) | 1.5236 (3) |
O(3)—H(4) | 0.926 (9) | C(2)—H(2) | 1.076 (7) |
N(1)—H(11) | 1.054 (9) | C(3)—H(31) | 1.107 (8) |
N(1)—H(12) | 1.025 (9) | C(3)—H(32) | 1.123 (8) |
| | | |
C(3)—O(3)—H(4) | 109.2 (4) | C(1)—C(2)—H(2) | 107.1 (4) |
H(11)—N(1)—H(12) | 107.8 (6) | C(3)—C(2)—H(2) | 109.6 (4) |
H(11)—N(1)—H(13) | 109.3 (6) | O(3)—C(3)—C(2) | 111.129 (17) |
H(12)—N(1)—H(13) | 109.3 (6) | O(3)—C(3)—H(31) | 107.9 (3) |
O(1)—C(1)—O(2) | 125.88 (2) | O(3)—C(3)—H(32) | 110.9 (4) |
O(1)—C(1)—C(2) | 117.815 (18) | C(2)—C(3)—H(31) | 108.2 (4) |
O(2)—C(1)—C(2) | 116.298 (18) | C(2)—C(3)—H(32) | 110.3 (4) |
C(1)—C(2)—C(3) | 111.284 (16) | H(31)—C(3)—H(32) | 108.4 (5) |
see manuscript