The crystal structure of
L-α-glutamine has been elucidated at room temperature at pressures between 0 and 4.9 GPa by using single-crystal high-pressure X-ray diffraction techniques. The structure is primarily stabilized by five N—H
O intermolecular interactions, which link molecules in a herringbone-like layer arrangement, giving rise to voids within the solid. The application of pressure on the structure results in a reduction in the size of the voids, as a consequence of the shortening of the N—H
O hydrogen bonds, which compress to minimum N
O distances of around 2.6 Å, without driving the crystal structure to a phase transition. The decrease in the hydrogen-bond distances is due to the necessary stabilization of the structure, which arises from molecules modifying their positions to optimize electrostatic contacts and minimize the occupied space. Hirshfeld surfaces and fingerprint plots have been used to rapidly assess the structural changes that occur on application of pressure.
Supporting information
CCDC references: 699591; 699592; 699593; 699594; 699595; 699596; 699597
For all compounds, data collection: SMART (Siemens, 1993); cell refinement: SAINT (Siemens ,1995); data reduction: SAINT (Siemens ,1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994). Program(s) used to refine structure: CRYSTALS (Watkin et al. 2001) for 0.0, 0.8, 1.4, 2.7, 3.6, 4.9; CRYSTALS (Betteridge et al. 2003) for 0.1. For all compounds, molecular graphics: CAMERON (Watkin et al. 1996). Software used to prepare material for publication: CRYSTALS (Watkin et al. 2001) for 0.0, 0.8, 1.4, 2.7, 3.6, 4.9; CRYSTALS (Betteridge et al. 2003) for 0.1.
Crystal data top
C5H10N2O3 | F(000) = 312.000 |
Mr = 146.15 | Dx = 1.529 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 16.023 (3) Å | Cell parameters from 348 reflections |
b = 7.7678 (18) Å | θ = 2.5–23.8° |
c = 5.1004 (13) Å | µ = 0.13 mm−1 |
V = 634.8 (2) Å3 | T = 293 K |
Z = 4 | Block, colourless |
Data collection top
Bruker SMART diffractometer | 202 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.184 |
φ & ω scans | θmax = 23.2°, θmin = 2.5° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −17→17 |
Tmin = 0.407, Tmax = 1.000 | k = −8→8 |
337 measured reflections | l = −3→3 |
326 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.105 | Fixed |
wR(F2) = 0.263 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)] 0.106 4.74 0.00 0.00 0.00 0.333 |
S = 1.05 | (Δ/σ)max = 0.000023 |
297 reflections | Δρmax = 0.57 e Å−3 |
41 parameters | Δρmin = −0.54 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4931 (8) | 0.5873 (19) | 0.727 (4) | 0.022 (5)* | |
C2 | 0.4116 (7) | 0.6671 (15) | 0.623 (4) | 0.020 (4)* | |
C3 | 0.3433 (8) | 0.5274 (16) | 0.625 (6) | 0.027 (5)* | |
C4 | 0.3644 (8) | 0.3758 (16) | 0.443 (6) | 0.027 (4)* | |
C5 | 0.2986 (8) | 0.2318 (17) | 0.454 (4) | 0.025 (5)* | |
N1 | 0.4239 (7) | 0.7498 (16) | 0.363 (4) | 0.021 (4)* | |
N2 | 0.3051 (8) | 0.1165 (17) | 0.257 (4) | 0.035 (4)* | |
O1 | 0.5494 (6) | 0.5646 (14) | 0.560 (4) | 0.037 (4)* | |
O2 | 0.2416 (6) | 0.2346 (13) | 0.621 (4) | 0.033 (3)* | |
O3 | 0.4911 (6) | 0.5404 (14) | 0.963 (4) | 0.030 (4)* | |
H10 | 0.3929 | 0.7627 | 0.7414 | 0.0253* | |
H2 | 0.3364 | 0.4834 | 0.8075 | 0.0334* | |
H3 | 0.2894 | 0.5804 | 0.5650 | 0.0334* | |
H8 | 0.4194 | 0.3269 | 0.4969 | 0.0346* | |
H6 | 0.3678 | 0.4189 | 0.2590 | 0.0346* | |
H5 | 0.3529 | 0.1234 | 0.1321 | 0.0427* | |
H4 | 0.2620 | 0.0240 | 0.2366 | 0.0427* | |
H9 | 0.4688 | 0.8387 | 0.3764 | 0.0256* | |
H1 | 0.4403 | 0.6605 | 0.2319 | 0.0256* | |
H7 | 0.3706 | 0.8059 | 0.3064 | 0.0256* | |
Geometric parameters (Å, º) top
C1—C2 | 1.539 (9) | C4—H8 | 0.998 |
C1—O1 | 1.253 (9) | C4—H6 | 0.996 |
C1—O3 | 1.258 (9) | C5—N2 | 1.353 (9) |
C2—C3 | 1.541 (9) | C5—O2 | 1.248 (9) |
C2—N1 | 1.49 (1) | N1—H9 | 0.999 |
C2—H10 | 1.002 | N1—H1 | 0.999 |
C3—C4 | 1.54 (1) | N1—H7 | 1.001 |
C3—H2 | 1.000 | N2—H5 | 0.996 |
C3—H3 | 1.003 | N2—H4 | 1.001 |
C4—C5 | 1.538 (9) | | |
| | | |
C2—C1—O1 | 115.7 (14) | C5—C4—H8 | 108.528 |
C2—C1—O3 | 115.0 (15) | C3—C4—H6 | 108.781 |
O1—C1—O3 | 128.9 (15) | C5—C4—H6 | 108.550 |
C1—C2—C3 | 108.5 (11) | H8—C4—H6 | 109.934 |
C1—C2—N1 | 111.6 (13) | C4—C5—N2 | 113.6 (14) |
C3—C2—N1 | 113.7 (16) | C4—C5—O2 | 121.1 (14) |
C1—C2—H10 | 110.227 | N2—C5—O2 | 125.1 (13) |
C3—C2—H10 | 107.833 | C2—N1—H9 | 109.442 |
N1—C2—H10 | 104.835 | C2—N1—H1 | 109.414 |
C2—C3—C4 | 112.3 (13) | H9—N1—H1 | 109.639 |
C2—C3—H2 | 108.811 | C2—N1—H7 | 109.431 |
C4—C3—H2 | 108.993 | H9—N1—H7 | 109.417 |
C2—C3—H3 | 108.681 | H1—N1—H7 | 109.484 |
C4—C3—H3 | 108.736 | C5—N2—H5 | 119.871 |
H2—C3—H3 | 109.253 | C5—N2—H4 | 119.858 |
C3—C4—C5 | 112.5 (12) | H5—N2—H4 | 120.270 |
C3—C4—H8 | 108.557 | | |
Crystal data top
C5H10N2O3 | F(000) = 312 |
Mr = 146.15 | Dx = 1.536 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 551 reflections |
a = 15.992 (2) Å | θ = 2.6–23.2° |
b = 7.7558 (12) Å | µ = 0.13 mm−1 |
c = 5.0941 (9) Å | T = 293 K |
V = 631.83 (17) Å3 | Block, colourless |
Z = 4 | |
Data collection top
Bruker SMART diffractometer | 205 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.224 |
φ & ω scans | θmax = 23.3°, θmin = 2.6° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −17→17 |
Tmin = 0.506, Tmax = 1.000 | k = −8→8 |
336 measured reflections | l = −2→02 |
324 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.148 | H-atom parameters not refined |
wR(F2) = 0.284 | P = P(6)*max(Fo2,0) + (1-P(6))Fc2
Method = SHELXL 97 (Sheldrick, 1997)
W = 1. / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)]
P(i) are:
0.00 11.6 0.00 0.00 0.00 0.333 |
S = 1.16 | (Δ/σ)max = 0.000024 |
267 reflections | Δρmax = 1.01 e Å−3 |
41 parameters | Δρmin = −0.76 e Å−3 |
9 restraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4926 (9) | 0.586 (3) | 0.729 (5) | 0.018 (7)* | |
C2 | 0.4111 (9) | 0.667 (2) | 0.628 (6) | 0.015 (6)* | |
C3 | 0.3440 (11) | 0.525 (2) | 0.630 (9) | 0.030 (7)* | |
C4 | 0.3654 (11) | 0.376 (2) | 0.441 (9) | 0.028 (6)* | |
C5 | 0.2979 (11) | 0.234 (2) | 0.446 (5) | 0.026 (7)* | |
N1 | 0.4244 (9) | 0.749 (2) | 0.368 (6) | 0.020 (5)* | |
N2 | 0.3051 (11) | 0.117 (2) | 0.251 (6) | 0.034 (6)* | |
O1 | 0.5492 (8) | 0.5668 (19) | 0.563 (5) | 0.031 (5)* | |
O2 | 0.2407 (8) | 0.2361 (18) | 0.612 (5) | 0.031 (5)* | |
O3 | 0.4924 (8) | 0.541 (2) | 0.965 (5) | 0.025 (5)* | |
H10 | 0.3914 | 0.7632 | 0.7434 | 0.0183* | |
H2 | 0.3391 | 0.4779 | 0.8119 | 0.0364* | |
H3 | 0.2893 | 0.5764 | 0.5756 | 0.0364* | |
H8 | 0.4201 | 0.3241 | 0.4950 | 0.0332* | |
H6 | 0.3701 | 0.4224 | 0.2588 | 0.0332* | |
H5 | 0.3530 | 0.1239 | 0.1251 | 0.0410* | |
H4 | 0.2627 | 0.0229 | 0.2331 | 0.0410* | |
H9 | 0.4687 | 0.8399 | 0.3830 | 0.0242* | |
H1 | 0.4424 | 0.6601 | 0.2380 | 0.0242* | |
H7 | 0.3710 | 0.8036 | 0.3072 | 0.0242* | |
Geometric parameters (Å, º) top
C1—C2 | 1.538 (9) | C4—H8 | 1.000 |
C1—O1 | 1.246 (9) | C4—H6 | 1.000 |
C1—O3 | 1.249 (10) | C5—N2 | 1.350 (10) |
C2—C3 | 1.539 (9) | C5—O2 | 1.246 (10) |
C2—N1 | 1.487 (10) | N1—H9 | 1.000 |
C2—H10 | 1.000 | N1—H1 | 1.000 |
C3—C4 | 1.542 (10) | N1—H7 | 1.000 |
C3—H2 | 1.000 | N2—H5 | 1.000 |
C3—H3 | 1.000 | N2—H4 | 1.000 |
C4—C5 | 1.540 (9) | | |
| | | |
C2—C1—O1 | 115.9 (18) | C5—C4—H8 | 108.904 |
C2—C1—O3 | 115.7 (19) | C3—C4—H6 | 108.896 |
O1—C1—O3 | 128.3 (19) | C5—C4—H6 | 108.909 |
C1—C2—C3 | 107.2 (14) | H8—C4—H6 | 109.470 |
C1—C2—N1 | 110.7 (18) | C4—C5—N2 | 114 (2) |
C3—C2—N1 | 114 (2) | C4—C5—O2 | 121 (2) |
C1—C2—H10 | 112.008 | N2—C5—O2 | 124.7 (17) |
C3—C2—H10 | 108.146 | C2—N1—H9 | 109.470 |
N1—C2—H10 | 104.459 | C2—N1—H1 | 109.467 |
C2—C3—C4 | 112.3 (18) | H9—N1—H1 | 109.480 |
C2—C3—H2 | 108.754 | C2—N1—H7 | 109.463 |
C4—C3—H2 | 108.765 | H9—N1—H7 | 109.474 |
C2—C3—H3 | 108.757 | H1—N1—H7 | 109.473 |
C4—C3—H3 | 108.765 | C5—N2—H5 | 120.002 |
H2—C3—H3 | 109.462 | C5—N2—H4 | 120.000 |
C3—C4—C5 | 111.7 (17) | H5—N2—H4 | 119.998 |
C3—C4—H8 | 108.894 | | |
Crystal data top
C5H10N2O3 | Dx = 1.561 Mg m−3 |
Mr = 146.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 347 reflections |
a = 15.879 (6) Å | θ = 2.6–22.5° |
b = 7.705 (3) Å | µ = 0.13 mm−1 |
c = 5.084 (2) Å | T = 293 K |
V = 622.0 (4) Å3 | Block, colourless |
Z = 4 | not measured × not measured × not measured mm |
F(000) = 312.000 | |
Data collection top
Bruker SMART diffractometer | 206 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.185 |
φ & ω scans | θmax = 23.4°, θmin = 2.6° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −17→17 |
Tmin = 0.487, Tmax = 1.000 | k = −8→8 |
341 measured reflections | l = −3→3 |
330 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.115 | Fixed |
wR(F2) = 0.249 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)] 0.550E-01 5.43 0.00 0.00 0.00 0.333 |
S = 1.04 | (Δ/σ)max = 0.000041 |
330 reflections | Δρmax = 0.71 e Å−3 |
41 parameters | Δρmin = −0.76 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4945 (7) | 0.593 (2) | 0.730 (4) | 0.025 (5)* | |
C2 | 0.4114 (7) | 0.6734 (16) | 0.633 (5) | 0.026 (5)* | |
C3 | 0.3423 (7) | 0.5337 (17) | 0.619 (6) | 0.029 (4)* | |
C4 | 0.3646 (8) | 0.3792 (16) | 0.440 (6) | 0.028 (4)* | |
C5 | 0.2980 (7) | 0.2350 (18) | 0.454 (4) | 0.027 (4)* | |
N1 | 0.4219 (6) | 0.7551 (16) | 0.370 (4) | 0.025 (3)* | |
N2 | 0.3047 (7) | 0.1155 (17) | 0.260 (4) | 0.033 (4)* | |
O1 | 0.5514 (6) | 0.5689 (13) | 0.566 (4) | 0.035 (3)* | |
O2 | 0.2425 (6) | 0.2336 (13) | 0.628 (4) | 0.034 (3)* | |
O3 | 0.4918 (6) | 0.5443 (14) | 0.965 (4) | 0.030 (3)* | |
H10 | 0.3945 | 0.7654 | 0.7618 | 0.0316* | |
H2 | 0.3321 | 0.4888 | 0.8007 | 0.0344* | |
H3 | 0.2897 | 0.5889 | 0.5504 | 0.0344* | |
H8 | 0.4201 | 0.3306 | 0.4968 | 0.0341* | |
H6 | 0.3687 | 0.4211 | 0.2546 | 0.0341* | |
H5 | 0.3510 | 0.1248 | 0.1279 | 0.0397* | |
H4 | 0.2634 | 0.0178 | 0.2498 | 0.0397* | |
H9 | 0.4668 | 0.8460 | 0.3793 | 0.0303* | |
H1 | 0.4384 | 0.6645 | 0.2390 | 0.0303* | |
H7 | 0.3675 | 0.8098 | 0.3150 | 0.0303* | |
Geometric parameters (Å, º) top
C1—C2 | 1.538 (9) | C4—H8 | 1.000 |
C1—O1 | 1.246 (9) | C4—H6 | 1.000 |
C1—O3 | 1.252 (9) | C5—N2 | 1.353 (9) |
C2—C3 | 1.539 (9) | C5—O2 | 1.247 (9) |
C2—N1 | 1.49 (1) | N1—H9 | 1.000 |
C2—H10 | 1.000 | N1—H1 | 1.000 |
C3—C4 | 1.54 (1) | N1—H7 | 1.001 |
C3—H2 | 1.001 | N2—H5 | 0.999 |
C3—H3 | 0.999 | N2—H4 | 1.000 |
C4—C5 | 1.536 (9) | | |
| | | |
C2—C1—O1 | 117.8 (14) | C5—C4—H8 | 108.859 |
C2—C1—O3 | 113.4 (14) | C3—C4—H6 | 108.759 |
O1—C1—O3 | 128.3 (14) | C5—C4—H6 | 108.819 |
C1—C2—C3 | 110.2 (11) | H8—C4—H6 | 109.514 |
C1—C2—N1 | 111.3 (13) | C4—C5—N2 | 113.8 (13) |
C3—C2—N1 | 109.4 (16) | C4—C5—O2 | 121.7 (15) |
C1—C2—H10 | 107.791 | N2—C5—O2 | 124.4 (12) |
C3—C2—H10 | 109.652 | C2—N1—H9 | 109.506 |
N1—C2—H10 | 108.499 | C2—N1—H1 | 109.491 |
C2—C3—C4 | 114.0 (13) | H9—N1—H1 | 109.471 |
C2—C3—H2 | 108.241 | C2—N1—H7 | 109.497 |
C4—C3—H2 | 108.314 | H9—N1—H7 | 109.452 |
C2—C3—H3 | 108.397 | H1—N1—H7 | 109.411 |
C4—C3—H3 | 108.426 | C5—N2—H5 | 120.018 |
H2—C3—H3 | 109.406 | C5—N2—H4 | 119.938 |
C3—C4—C5 | 112.0 (12) | H5—N2—H4 | 120.044 |
C3—C4—H8 | 108.835 | | |
Crystal data top
C5H10N2O3 | Dx = 1.616 Mg m−3 |
Mr = 146.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 313 reflections |
a = 15.679 (11) Å | θ = 2.6–23.6° |
b = 7.628 (6) Å | µ = 0.13 mm−1 |
c = 5.023 (5) Å | T = 293 K |
V = 600.8 (9) Å3 | Block, colourless |
Z = 4 | not measured × not measured × not measured mm |
F(000) = 312.000 | |
Data collection top
Bruker SMART diffractometer | 202 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.155 |
φ & ω scans | θmax = 23.3°, θmin = 2.6° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −17→17 |
Tmin = 0.657, Tmax = 1.000 | k = −8→8 |
305 measured reflections | l = −2→2 |
295 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.243 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)] 0.897E-01 4.49 0.00 0.00 0.00 0.333 |
S = 1.04 | (Δ/σ)max = 0.000042 |
295 reflections | Δρmax = 0.76 e Å−3 |
41 parameters | Δρmin = −0.55 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4947 (7) | 0.597 (2) | 0.733 (4) | 0.022 (4)* | |
C2 | 0.4109 (7) | 0.6788 (15) | 0.636 (4) | 0.019 (4)* | |
C3 | 0.3417 (7) | 0.5369 (15) | 0.624 (6) | 0.020 (4)* | |
C4 | 0.3634 (8) | 0.3816 (15) | 0.441 (6) | 0.021 (4)* | |
C5 | 0.2976 (8) | 0.2333 (18) | 0.459 (4) | 0.023 (4)* | |
N1 | 0.4212 (7) | 0.7622 (16) | 0.370 (4) | 0.024 (3)* | |
N2 | 0.3039 (7) | 0.1159 (17) | 0.260 (4) | 0.034 (4)* | |
O1 | 0.5524 (6) | 0.5745 (13) | 0.565 (4) | 0.033 (3)* | |
O2 | 0.2428 (6) | 0.2347 (13) | 0.637 (4) | 0.033 (3)* | |
O3 | 0.4939 (6) | 0.5498 (14) | 0.972 (4) | 0.032 (4)* | |
H10 | 0.3938 | 0.7725 | 0.7643 | 0.0223* | |
H2 | 0.3327 | 0.4907 | 0.8080 | 0.0237* | |
H3 | 0.2879 | 0.5921 | 0.5582 | 0.0237* | |
H8 | 0.4206 | 0.3344 | 0.4925 | 0.0251* | |
H6 | 0.3656 | 0.4245 | 0.2527 | 0.0251* | |
H5 | 0.3508 | 0.1266 | 0.1256 | 0.0407* | |
H4 | 0.2617 | 0.0181 | 0.2456 | 0.0407* | |
H9 | 0.4664 | 0.8544 | 0.3797 | 0.0285* | |
H1 | 0.4381 | 0.6713 | 0.2365 | 0.0285* | |
H7 | 0.3660 | 0.8169 | 0.3148 | 0.0285* | |
Geometric parameters (Å, º) top
C1—C2 | 1.533 (9) | C4—H8 | 1.000 |
C1—O1 | 1.250 (9) | C4—H6 | 1.000 |
C1—O3 | 1.253 (9) | C5—N2 | 1.35 (1) |
C2—C3 | 1.533 (9) | C5—O2 | 1.241 (9) |
C2—N1 | 1.49 (1) | N1—H9 | 1.000 |
C2—H10 | 1.000 | N1—H1 | 1.000 |
C3—C4 | 1.54 (1) | N1—H7 | 1.000 |
C3—H2 | 1.001 | N2—H5 | 1.000 |
C3—H3 | 1.000 | N2—H4 | 1.000 |
C4—C5 | 1.534 (9) | | |
| | | |
C2—C1—O1 | 117.4 (13) | C5—C4—H8 | 108.699 |
C2—C1—O3 | 114.5 (14) | C3—C4—H6 | 108.665 |
O1—C1—O3 | 127.9 (14) | C5—C4—H6 | 108.702 |
C1—C2—C3 | 109.4 (10) | H8—C4—H6 | 109.481 |
C1—C2—N1 | 111.5 (13) | C4—C5—N2 | 113.4 (13) |
C3—C2—N1 | 110.0 (15) | C4—C5—O2 | 120.2 (14) |
C1—C2—H10 | 108.333 | N2—C5—O2 | 126.3 (12) |
C3—C2—H10 | 109.863 | C2—N1—H9 | 109.453 |
N1—C2—H10 | 107.637 | C2—N1—H1 | 109.471 |
C2—C3—C4 | 114.3 (12) | H9—N1—H1 | 109.492 |
C2—C3—H2 | 108.235 | C2—N1—H7 | 109.450 |
C4—C3—H2 | 108.238 | H9—N1—H7 | 109.469 |
C2—C3—H3 | 108.293 | H1—N1—H7 | 109.492 |
C4—C3—H3 | 108.305 | C5—N2—H5 | 120.000 |
H2—C3—H3 | 109.452 | C5—N2—H4 | 120.007 |
C3—C4—C5 | 112.5 (12) | H5—N2—H4 | 119.993 |
C3—C4—H8 | 108.710 | | |
Crystal data top
C5H10N2O3 | Dx = 1.674 Mg m−3 |
Mr = 146.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 325 reflections |
a = 15.450 (8) Å | θ = 2.6–21.3° |
b = 7.550 (6) Å | µ = 0.14 mm−1 |
c = 4.972 (5) Å | T = 293 K |
V = 580.0 (7) Å3 | Block, colourless |
Z = 4 | not measured × not measured × not measured mm |
F(000) = 312.000 | |
Data collection top
Bruker SMART diffractometer | 190 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.140 |
φ & ω scans | θmax = 23.3°, θmin = 2.6° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −17→17 |
Tmin = 0.557, Tmax = 1.000 | k = −8→8 |
281 measured reflections | l = −3→3 |
271 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.178 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)] 0.622E-01 1.70 0.00 0.00 0.00 0.333 |
S = 1.02 | (Δ/σ)max = 0.000028 |
271 reflections | Δρmax = 0.40 e Å−3 |
41 parameters | Δρmin = −0.39 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4937 (6) | 0.6050 (16) | 0.735 (3) | 0.029 (4)* | |
C2 | 0.4085 (6) | 0.6870 (13) | 0.634 (4) | 0.032 (4)* | |
C3 | 0.3404 (5) | 0.5398 (13) | 0.629 (4) | 0.024 (3)* | |
C4 | 0.3647 (6) | 0.3874 (13) | 0.437 (5) | 0.030 (3)* | |
C5 | 0.2993 (6) | 0.2369 (14) | 0.458 (3) | 0.025 (3)* | |
N1 | 0.4205 (5) | 0.7699 (13) | 0.366 (3) | 0.030 (3)* | |
N2 | 0.3023 (5) | 0.1196 (13) | 0.254 (3) | 0.033 (3)* | |
O1 | 0.5533 (4) | 0.585 (1) | 0.570 (3) | 0.037 (3)* | |
O2 | 0.2466 (5) | 0.232 (1) | 0.647 (3) | 0.041 (3)* | |
O3 | 0.4944 (5) | 0.5602 (11) | 0.977 (3) | 0.037 (3)* | |
H10 | 0.3910 | 0.7849 | 0.7578 | 0.0382* | |
H2 | 0.3318 | 0.4945 | 0.8131 | 0.0263* | |
H3 | 0.2841 | 0.5949 | 0.5629 | 0.0263* | |
H8 | 0.4232 | 0.3430 | 0.4913 | 0.0349* | |
H6 | 0.3668 | 0.4331 | 0.2495 | 0.0349* | |
H5 | 0.3470 | 0.1340 | 0.1091 | 0.0405* | |
H4 | 0.2616 | 0.0175 | 0.2493 | 0.0405* | |
H9 | 0.4653 | 0.8639 | 0.3743 | 0.0367* | |
H1 | 0.4379 | 0.6773 | 0.2318 | 0.0367* | |
H7 | 0.3638 | 0.8237 | 0.3061 | 0.0367* | |
Geometric parameters (Å, º) top
C1—C2 | 1.539 (9) | C4—H8 | 1.000 |
C1—O1 | 1.243 (9) | C4—H6 | 0.995 |
C1—O3 | 1.250 (9) | C5—N2 | 1.348 (9) |
C2—C3 | 1.531 (8) | C5—O2 | 1.243 (9) |
C2—N1 | 1.486 (9) | N1—H9 | 0.993 |
C2—H10 | 0.999 | N1—H1 | 1.003 |
C3—C4 | 1.541 (9) | N1—H7 | 1.009 |
C3—H2 | 0.987 | N2—H5 | 1.004 |
C3—H3 | 1.018 | N2—H4 | 0.995 |
C4—C5 | 1.525 (8) | | |
| | | |
C2—C1—O1 | 117.8 (11) | C5—C4—H8 | 109.345 |
C2—C1—O3 | 115.6 (11) | C3—C4—H6 | 109.185 |
O1—C1—O3 | 126.6 (11) | C5—C4—H6 | 110.200 |
C1—C2—C3 | 107.6 (8) | H8—C4—H6 | 109.810 |
C1—C2—N1 | 110.9 (10) | C4—C5—N2 | 114.4 (11) |
C3—C2—N1 | 112.1 (12) | C4—C5—O2 | 120.6 (11) |
C1—C2—H10 | 109.133 | N2—C5—O2 | 124.9 (10) |
C3—C2—H10 | 111.217 | C2—N1—H9 | 110.474 |
N1—C2—H10 | 105.935 | C2—N1—H1 | 109.679 |
C2—C3—C4 | 112.6 (9) | H9—N1—H1 | 109.837 |
C2—C3—H2 | 109.113 | C2—N1—H7 | 109.025 |
C4—C3—H2 | 110.368 | H9—N1—H7 | 109.276 |
C2—C3—H3 | 107.239 | H1—N1—H7 | 108.516 |
C4—C3—H3 | 108.339 | C5—N2—H5 | 119.622 |
H2—C3—H3 | 109.039 | C5—N2—H4 | 120.283 |
C3—C4—C5 | 110.6 (9) | H5—N2—H4 | 120.074 |
C3—C4—H8 | 107.673 | | |
Crystal data top
C5H10N2O3 | Dx = 1.710 Mg m−3 |
Mr = 146.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 384 reflections |
a = 15.328 (7) Å | θ = 2.7–23.1° |
b = 7.497 (5) Å | µ = 0.14 mm−1 |
c = 4.941 (4) Å | T = 293 K |
V = 567.8 (6) Å3 | Block, colourless |
Z = 4 | not measured × not measured × not measured mm |
F(000) = 312.000 | |
Data collection top
Bruker SMART diffractometer | 196 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.144 |
φ & ω scans | θmax = 23.4°, θmin = 2.7° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −17→16 |
Tmin = 0.307, Tmax = 1.000 | k = −8→8 |
281 measured reflections | l = −2→2 |
270 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.188 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)] 0.344E-01 3.13 0.00 0.00 0.00 0.333 |
S = 1.09 | (Δ/σ)max = 0.000043 |
270 reflections | Δρmax = 0.53 e Å−3 |
41 parameters | Δρmin = −0.54 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4949 (7) | 0.6128 (18) | 0.733 (3) | 0.033 (4)* | |
C2 | 0.4084 (6) | 0.6919 (15) | 0.637 (4) | 0.030 (4)* | |
C3 | 0.3396 (6) | 0.5435 (14) | 0.630 (5) | 0.018 (3)* | |
C4 | 0.3644 (7) | 0.3933 (14) | 0.432 (5) | 0.026 (4)* | |
C5 | 0.3005 (7) | 0.2389 (15) | 0.468 (3) | 0.025 (4)* | |
N1 | 0.4184 (6) | 0.7714 (15) | 0.363 (4) | 0.029 (3)* | |
N2 | 0.3014 (6) | 0.1220 (14) | 0.262 (3) | 0.030 (3)* | |
O1 | 0.5543 (5) | 0.5883 (12) | 0.566 (4) | 0.041 (3)* | |
O2 | 0.2478 (5) | 0.2330 (12) | 0.657 (3) | 0.039 (3)* | |
O3 | 0.4952 (5) | 0.5638 (13) | 0.975 (3) | 0.033 (3)* | |
H10 | 0.3900 | 0.7874 | 0.7656 | 0.0369* | |
H2 | 0.3334 | 0.4916 | 0.8149 | 0.0210* | |
H3 | 0.2826 | 0.5961 | 0.5713 | 0.0210* | |
H8 | 0.4251 | 0.3516 | 0.4703 | 0.0311* | |
H6 | 0.3611 | 0.4385 | 0.2414 | 0.0311* | |
H5 | 0.3460 | 0.1342 | 0.1149 | 0.0370* | |
H4 | 0.2578 | 0.0232 | 0.2554 | 0.0370* | |
H9 | 0.4633 | 0.8676 | 0.3692 | 0.0349* | |
H1 | 0.4369 | 0.6768 | 0.2323 | 0.0349* | |
H7 | 0.3612 | 0.8225 | 0.3039 | 0.0349* | |
Geometric parameters (Å, º) top
C1—C2 | 1.528 (9) | C4—H8 | 0.999 |
C1—O1 | 1.243 (9) | C4—H6 | 1.004 |
C1—O3 | 1.247 (9) | C5—N2 | 1.342 (9) |
C2—C3 | 1.533 (9) | C5—O2 | 1.238 (9) |
C2—N1 | 1.49 (1) | N1—H9 | 0.997 |
C2—H10 | 0.998 | N1—H1 | 1.000 |
C3—C4 | 1.54 (1) | N1—H7 | 1.001 |
C3—H2 | 0.998 | N2—H5 | 1.001 |
C3—H3 | 1.001 | N2—H4 | 0.998 |
C4—C5 | 1.526 (9) | | |
| | | |
C2—C1—O1 | 119.0 (12) | C5—C4—H8 | 109.824 |
C2—C1—O3 | 114.6 (12) | C3—C4—H6 | 109.670 |
O1—C1—O3 | 126.1 (13) | C5—C4—H6 | 109.337 |
C1—C2—C3 | 108.8 (10) | H8—C4—H6 | 109.219 |
C1—C2—N1 | 110.5 (11) | C4—C5—N2 | 113.7 (11) |
C3—C2—N1 | 109.9 (12) | C4—C5—O2 | 122.2 (12) |
C1—C2—H10 | 108.962 | N2—C5—O2 | 123.8 (10) |
C3—C2—H10 | 109.916 | C2—N1—H9 | 109.457 |
N1—C2—H10 | 108.713 | C2—N1—H1 | 109.391 |
C2—C3—C4 | 112.1 (10) | H9—N1—H1 | 109.696 |
C2—C3—H2 | 109.164 | C2—N1—H7 | 109.197 |
C4—C3—H2 | 108.641 | H9—N1—H7 | 109.686 |
C2—C3—H3 | 108.728 | H1—N1—H7 | 109.398 |
C4—C3—H3 | 108.637 | C5—N2—H5 | 119.781 |
H2—C3—H3 | 109.542 | C5—N2—H4 | 120.139 |
C3—C4—C5 | 108.9 (10) | H5—N2—H4 | 120.080 |
C3—C4—H8 | 109.827 | | |
Crystal data top
C5H10N2O3 | Dx = 1.756 Mg m−3 |
Mr = 146.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 190 reflections |
a = 15.191 (8) Å | θ = 5.4–22.5° |
b = 7.455 (5) Å | µ = 0.15 mm−1 |
c = 4.882 (4) Å | T = 293 K |
V = 552.8 (6) Å3 | Block, colourless |
Z = 4 | 0.00 × 0.00 × 0.00 mm |
F(000) = 312.000 | |
Data collection top
Bruker SMART diffractometer | 182 reflections with I > 2.00u(I) |
Graphite monochromator | Rint = 0.214 |
φ & ω scans | θmax = 23.2°, θmin = 2.7° |
Absorption correction: multi-scan SORTAV (Blessing) | h = −16→16 |
Tmin = 0.722, Tmax = 1.000 | k = 8→8 |
292 measured reflections | l = −3→3 |
283 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.183 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)] 0.00 3.26 0.00 0.00 0.00 0.333 |
S = 1.10 | (Δ/σ)max = 0.000027 |
278 reflections | Δρmax = 1.00 e Å−3 |
41 parameters | Δρmin = −1.05 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4946 (8) | 0.619 (2) | 0.736 (4) | 0.025 (5)* | |
C2 | 0.4083 (8) | 0.6962 (17) | 0.623 (5) | 0.028 (5)* | |
C3 | 0.3386 (8) | 0.5471 (16) | 0.625 (5) | 0.024 (5)* | |
C4 | 0.3657 (8) | 0.3955 (16) | 0.429 (5) | 0.019 (4)* | |
C5 | 0.2995 (9) | 0.2424 (18) | 0.468 (4) | 0.029 (5)* | |
N1 | 0.4169 (8) | 0.7804 (18) | 0.348 (5) | 0.033 (4)* | |
N2 | 0.3006 (8) | 0.1232 (18) | 0.260 (4) | 0.032 (4)* | |
O1 | 0.5562 (6) | 0.5959 (14) | 0.569 (4) | 0.033 (3)* | |
O2 | 0.2504 (7) | 0.2316 (14) | 0.673 (4) | 0.037 (4)* | |
O3 | 0.4959 (6) | 0.5678 (16) | 0.980 (4) | 0.038 (4)* | |
H10 | 0.3898 | 0.7972 | 0.7446 | 0.0336* | |
H2 | 0.3330 | 0.4979 | 0.8151 | 0.0286* | |
H3 | 0.2807 | 0.5978 | 0.5658 | 0.0286* | |
H8 | 0.4265 | 0.3532 | 0.4731 | 0.0225* | |
H6 | 0.3639 | 0.4392 | 0.2350 | 0.0225* | |
H5 | 0.3419 | 0.1409 | 0.1022 | 0.0389* | |
H4 | 0.2603 | 0.0172 | 0.2626 | 0.0389* | |
H9 | 0.4628 | 0.8765 | 0.3552 | 0.0400* | |
H1 | 0.4345 | 0.6873 | 0.2112 | 0.0400* | |
H7 | 0.3592 | 0.8341 | 0.2934 | 0.0400* | |
Geometric parameters (Å, º) top
C1—C2 | 1.535 (9) | C4—H8 | 1.000 |
C1—O1 | 1.253 (9) | C4—H6 | 1.000 |
C1—O3 | 1.252 (9) | C5—N2 | 1.351 (9) |
C2—C3 | 1.535 (9) | C5—O2 | 1.249 (9) |
C2—N1 | 1.49 (1) | N1—H9 | 1.000 |
C2—H10 | 1.000 | N1—H1 | 1.000 |
C3—C4 | 1.539 (9) | N1—H7 | 1.000 |
C3—H2 | 1.000 | N2—H5 | 1.000 |
C3—H3 | 1.000 | N2—H4 | 1.000 |
C4—C5 | 1.534 (9) | | |
| | | |
C2—C1—O1 | 117.0 (14) | C5—C4—H8 | 110.072 |
C2—C1—O3 | 118.1 (14) | C3—C4—H6 | 110.086 |
O1—C1—O3 | 124.5 (15) | C5—C4—H6 | 110.072 |
C1—C2—C3 | 108.3 (11) | H8—C4—H6 | 109.458 |
C1—C2—N1 | 114.1 (14) | C4—C5—N2 | 112.7 (12) |
C3—C2—N1 | 112.0 (14) | C4—C5—O2 | 122.6 (13) |
C1—C2—H10 | 107.961 | N2—C5—O2 | 124.6 (13) |
C3—C2—H10 | 110.293 | C2—N1—H9 | 109.466 |
N1—C2—H10 | 104.045 | C2—N1—H1 | 109.460 |
C2—C3—C4 | 110.0 (12) | H9—N1—H1 | 109.472 |
C2—C3—H2 | 109.354 | C2—N1—H7 | 109.470 |
C4—C3—H2 | 109.341 | H9—N1—H7 | 109.484 |
C2—C3—H3 | 109.328 | H1—N1—H7 | 109.476 |
C4—C3—H3 | 109.321 | C5—N2—H5 | 119.996 |
H2—C3—H3 | 109.472 | C5—N2—H4 | 120.004 |
C3—C4—C5 | 107.0 (11) | H5—N2—H4 | 120.000 |
C3—C4—H8 | 110.076 | | |