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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810801793X/bm5054sup1.cif
Contains datablocks 0.0, 0.1, 0.8, 1.4, 2.7, 3.6, 4.9

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50540.0sup2.hkl
Contains datablock 0.0

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50540.1sup3.hkl
Contains datablock 0.1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50540.8sup4.hkl
Contains datablock 0.8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50541.4sup5.hkl
Contains datablock 1.4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50542.7sup6.hkl
Contains datablock 2.7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50543.6sup7.hkl
Contains datablock 3.6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810801793X/bm50544.9sup8.hkl
Contains datablock 4.9

CCDC references: 699591; 699592; 699593; 699594; 699595; 699596; 699597

Computing details top

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.

(0.0) top
Crystal data top
C5H10N2O3F(000) = 312.000
Mr = 146.15Dx = 1.529 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 16.023 (3) ÅCell parameters from 348 reflections
b = 7.7678 (18) Åθ = 2.5–23.8°
c = 5.1004 (13) ŵ = 0.13 mm1
V = 634.8 (2) Å3T = 293 K
Z = 4Block, colourless
Data collection top
Bruker SMART
diffractometer
202 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.184
φ & ω scansθmax = 23.2°, θmin = 2.5°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1717
Tmin = 0.407, Tmax = 1.000k = 88
337 measured reflectionsl = 33
326 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.105Fixed
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 reflectionsΔρmax = 0.57 e Å3
41 parametersΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4931 (8)0.5873 (19)0.727 (4)0.022 (5)*
C20.4116 (7)0.6671 (15)0.623 (4)0.020 (4)*
C30.3433 (8)0.5274 (16)0.625 (6)0.027 (5)*
C40.3644 (8)0.3758 (16)0.443 (6)0.027 (4)*
C50.2986 (8)0.2318 (17)0.454 (4)0.025 (5)*
N10.4239 (7)0.7498 (16)0.363 (4)0.021 (4)*
N20.3051 (8)0.1165 (17)0.257 (4)0.035 (4)*
O10.5494 (6)0.5646 (14)0.560 (4)0.037 (4)*
O20.2416 (6)0.2346 (13)0.621 (4)0.033 (3)*
O30.4911 (6)0.5404 (14)0.963 (4)0.030 (4)*
H100.39290.76270.74140.0253*
H20.33640.48340.80750.0334*
H30.28940.58040.56500.0334*
H80.41940.32690.49690.0346*
H60.36780.41890.25900.0346*
H50.35290.12340.13210.0427*
H40.26200.02400.23660.0427*
H90.46880.83870.37640.0256*
H10.44030.66050.23190.0256*
H70.37060.80590.30640.0256*
Geometric parameters (Å, º) top
C1—C21.539 (9)C4—H80.998
C1—O11.253 (9)C4—H60.996
C1—O31.258 (9)C5—N21.353 (9)
C2—C31.541 (9)C5—O21.248 (9)
C2—N11.49 (1)N1—H90.999
C2—H101.002N1—H10.999
C3—C41.54 (1)N1—H71.001
C3—H21.000N2—H50.996
C3—H31.003N2—H41.001
C4—C51.538 (9)
C2—C1—O1115.7 (14)C5—C4—H8108.528
C2—C1—O3115.0 (15)C3—C4—H6108.781
O1—C1—O3128.9 (15)C5—C4—H6108.550
C1—C2—C3108.5 (11)H8—C4—H6109.934
C1—C2—N1111.6 (13)C4—C5—N2113.6 (14)
C3—C2—N1113.7 (16)C4—C5—O2121.1 (14)
C1—C2—H10110.227N2—C5—O2125.1 (13)
C3—C2—H10107.833C2—N1—H9109.442
N1—C2—H10104.835C2—N1—H1109.414
C2—C3—C4112.3 (13)H9—N1—H1109.639
C2—C3—H2108.811C2—N1—H7109.431
C4—C3—H2108.993H9—N1—H7109.417
C2—C3—H3108.681H1—N1—H7109.484
C4—C3—H3108.736C5—N2—H5119.871
H2—C3—H3109.253C5—N2—H4119.858
C3—C4—C5112.5 (12)H5—N2—H4120.270
C3—C4—H8108.557
(0.1) top
Crystal data top
C5H10N2O3F(000) = 312
Mr = 146.15Dx = 1.536 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 551 reflections
a = 15.992 (2) Åθ = 2.6–23.2°
b = 7.7558 (12) ŵ = 0.13 mm1
c = 5.0941 (9) ÅT = 293 K
V = 631.83 (17) Å3Block, colourless
Z = 4
Data collection top
Bruker SMART
diffractometer
205 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.224
φ & ω scansθmax = 23.3°, θmin = 2.6°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1717
Tmin = 0.506, Tmax = 1.000k = 88
336 measured reflectionsl = 202
324 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.148H-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 reflectionsΔρmax = 1.01 e Å3
41 parametersΔρmin = 0.76 e Å3
9 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4926 (9)0.586 (3)0.729 (5)0.018 (7)*
C20.4111 (9)0.667 (2)0.628 (6)0.015 (6)*
C30.3440 (11)0.525 (2)0.630 (9)0.030 (7)*
C40.3654 (11)0.376 (2)0.441 (9)0.028 (6)*
C50.2979 (11)0.234 (2)0.446 (5)0.026 (7)*
N10.4244 (9)0.749 (2)0.368 (6)0.020 (5)*
N20.3051 (11)0.117 (2)0.251 (6)0.034 (6)*
O10.5492 (8)0.5668 (19)0.563 (5)0.031 (5)*
O20.2407 (8)0.2361 (18)0.612 (5)0.031 (5)*
O30.4924 (8)0.541 (2)0.965 (5)0.025 (5)*
H100.39140.76320.74340.0183*
H20.33910.47790.81190.0364*
H30.28930.57640.57560.0364*
H80.42010.32410.49500.0332*
H60.37010.42240.25880.0332*
H50.35300.12390.12510.0410*
H40.26270.02290.23310.0410*
H90.46870.83990.38300.0242*
H10.44240.66010.23800.0242*
H70.37100.80360.30720.0242*
Geometric parameters (Å, º) top
C1—C21.538 (9)C4—H81.000
C1—O11.246 (9)C4—H61.000
C1—O31.249 (10)C5—N21.350 (10)
C2—C31.539 (9)C5—O21.246 (10)
C2—N11.487 (10)N1—H91.000
C2—H101.000N1—H11.000
C3—C41.542 (10)N1—H71.000
C3—H21.000N2—H51.000
C3—H31.000N2—H41.000
C4—C51.540 (9)
C2—C1—O1115.9 (18)C5—C4—H8108.904
C2—C1—O3115.7 (19)C3—C4—H6108.896
O1—C1—O3128.3 (19)C5—C4—H6108.909
C1—C2—C3107.2 (14)H8—C4—H6109.470
C1—C2—N1110.7 (18)C4—C5—N2114 (2)
C3—C2—N1114 (2)C4—C5—O2121 (2)
C1—C2—H10112.008N2—C5—O2124.7 (17)
C3—C2—H10108.146C2—N1—H9109.470
N1—C2—H10104.459C2—N1—H1109.467
C2—C3—C4112.3 (18)H9—N1—H1109.480
C2—C3—H2108.754C2—N1—H7109.463
C4—C3—H2108.765H9—N1—H7109.474
C2—C3—H3108.757H1—N1—H7109.473
C4—C3—H3108.765C5—N2—H5120.002
H2—C3—H3109.462C5—N2—H4120.000
C3—C4—C5111.7 (17)H5—N2—H4119.998
C3—C4—H8108.894
(0.8) top
Crystal data top
C5H10N2O3Dx = 1.561 Mg m3
Mr = 146.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 347 reflections
a = 15.879 (6) Åθ = 2.6–22.5°
b = 7.705 (3) ŵ = 0.13 mm1
c = 5.084 (2) ÅT = 293 K
V = 622.0 (4) Å3Block, colourless
Z = 4not measured × not measured × not measured mm
F(000) = 312.000
Data collection top
Bruker SMART
diffractometer
206 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.185
φ & ω scansθmax = 23.4°, θmin = 2.6°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1717
Tmin = 0.487, Tmax = 1.000k = 88
341 measured reflectionsl = 33
330 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.115Fixed
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 reflectionsΔρmax = 0.71 e Å3
41 parametersΔρmin = 0.76 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4945 (7)0.593 (2)0.730 (4)0.025 (5)*
C20.4114 (7)0.6734 (16)0.633 (5)0.026 (5)*
C30.3423 (7)0.5337 (17)0.619 (6)0.029 (4)*
C40.3646 (8)0.3792 (16)0.440 (6)0.028 (4)*
C50.2980 (7)0.2350 (18)0.454 (4)0.027 (4)*
N10.4219 (6)0.7551 (16)0.370 (4)0.025 (3)*
N20.3047 (7)0.1155 (17)0.260 (4)0.033 (4)*
O10.5514 (6)0.5689 (13)0.566 (4)0.035 (3)*
O20.2425 (6)0.2336 (13)0.628 (4)0.034 (3)*
O30.4918 (6)0.5443 (14)0.965 (4)0.030 (3)*
H100.39450.76540.76180.0316*
H20.33210.48880.80070.0344*
H30.28970.58890.55040.0344*
H80.42010.33060.49680.0341*
H60.36870.42110.25460.0341*
H50.35100.12480.12790.0397*
H40.26340.01780.24980.0397*
H90.46680.84600.37930.0303*
H10.43840.66450.23900.0303*
H70.36750.80980.31500.0303*
Geometric parameters (Å, º) top
C1—C21.538 (9)C4—H81.000
C1—O11.246 (9)C4—H61.000
C1—O31.252 (9)C5—N21.353 (9)
C2—C31.539 (9)C5—O21.247 (9)
C2—N11.49 (1)N1—H91.000
C2—H101.000N1—H11.000
C3—C41.54 (1)N1—H71.001
C3—H21.001N2—H50.999
C3—H30.999N2—H41.000
C4—C51.536 (9)
C2—C1—O1117.8 (14)C5—C4—H8108.859
C2—C1—O3113.4 (14)C3—C4—H6108.759
O1—C1—O3128.3 (14)C5—C4—H6108.819
C1—C2—C3110.2 (11)H8—C4—H6109.514
C1—C2—N1111.3 (13)C4—C5—N2113.8 (13)
C3—C2—N1109.4 (16)C4—C5—O2121.7 (15)
C1—C2—H10107.791N2—C5—O2124.4 (12)
C3—C2—H10109.652C2—N1—H9109.506
N1—C2—H10108.499C2—N1—H1109.491
C2—C3—C4114.0 (13)H9—N1—H1109.471
C2—C3—H2108.241C2—N1—H7109.497
C4—C3—H2108.314H9—N1—H7109.452
C2—C3—H3108.397H1—N1—H7109.411
C4—C3—H3108.426C5—N2—H5120.018
H2—C3—H3109.406C5—N2—H4119.938
C3—C4—C5112.0 (12)H5—N2—H4120.044
C3—C4—H8108.835
(1.4) top
Crystal data top
C5H10N2O3Dx = 1.616 Mg m3
Mr = 146.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 313 reflections
a = 15.679 (11) Åθ = 2.6–23.6°
b = 7.628 (6) ŵ = 0.13 mm1
c = 5.023 (5) ÅT = 293 K
V = 600.8 (9) Å3Block, colourless
Z = 4not measured × not measured × not measured mm
F(000) = 312.000
Data collection top
Bruker SMART
diffractometer
202 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.155
φ & ω scansθmax = 23.3°, θmin = 2.6°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1717
Tmin = 0.657, Tmax = 1.000k = 88
305 measured reflectionsl = 22
295 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.107H 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 reflectionsΔρmax = 0.76 e Å3
41 parametersΔρmin = 0.55 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4947 (7)0.597 (2)0.733 (4)0.022 (4)*
C20.4109 (7)0.6788 (15)0.636 (4)0.019 (4)*
C30.3417 (7)0.5369 (15)0.624 (6)0.020 (4)*
C40.3634 (8)0.3816 (15)0.441 (6)0.021 (4)*
C50.2976 (8)0.2333 (18)0.459 (4)0.023 (4)*
N10.4212 (7)0.7622 (16)0.370 (4)0.024 (3)*
N20.3039 (7)0.1159 (17)0.260 (4)0.034 (4)*
O10.5524 (6)0.5745 (13)0.565 (4)0.033 (3)*
O20.2428 (6)0.2347 (13)0.637 (4)0.033 (3)*
O30.4939 (6)0.5498 (14)0.972 (4)0.032 (4)*
H100.39380.77250.76430.0223*
H20.33270.49070.80800.0237*
H30.28790.59210.55820.0237*
H80.42060.33440.49250.0251*
H60.36560.42450.25270.0251*
H50.35080.12660.12560.0407*
H40.26170.01810.24560.0407*
H90.46640.85440.37970.0285*
H10.43810.67130.23650.0285*
H70.36600.81690.31480.0285*
Geometric parameters (Å, º) top
C1—C21.533 (9)C4—H81.000
C1—O11.250 (9)C4—H61.000
C1—O31.253 (9)C5—N21.35 (1)
C2—C31.533 (9)C5—O21.241 (9)
C2—N11.49 (1)N1—H91.000
C2—H101.000N1—H11.000
C3—C41.54 (1)N1—H71.000
C3—H21.001N2—H51.000
C3—H31.000N2—H41.000
C4—C51.534 (9)
C2—C1—O1117.4 (13)C5—C4—H8108.699
C2—C1—O3114.5 (14)C3—C4—H6108.665
O1—C1—O3127.9 (14)C5—C4—H6108.702
C1—C2—C3109.4 (10)H8—C4—H6109.481
C1—C2—N1111.5 (13)C4—C5—N2113.4 (13)
C3—C2—N1110.0 (15)C4—C5—O2120.2 (14)
C1—C2—H10108.333N2—C5—O2126.3 (12)
C3—C2—H10109.863C2—N1—H9109.453
N1—C2—H10107.637C2—N1—H1109.471
C2—C3—C4114.3 (12)H9—N1—H1109.492
C2—C3—H2108.235C2—N1—H7109.450
C4—C3—H2108.238H9—N1—H7109.469
C2—C3—H3108.293H1—N1—H7109.492
C4—C3—H3108.305C5—N2—H5120.000
H2—C3—H3109.452C5—N2—H4120.007
C3—C4—C5112.5 (12)H5—N2—H4119.993
C3—C4—H8108.710
(2.7) top
Crystal data top
C5H10N2O3Dx = 1.674 Mg m3
Mr = 146.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 325 reflections
a = 15.450 (8) Åθ = 2.6–21.3°
b = 7.550 (6) ŵ = 0.14 mm1
c = 4.972 (5) ÅT = 293 K
V = 580.0 (7) Å3Block, colourless
Z = 4not measured × not measured × not measured mm
F(000) = 312.000
Data collection top
Bruker SMART
diffractometer
190 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.140
φ & ω scansθmax = 23.3°, θmin = 2.6°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1717
Tmin = 0.557, Tmax = 1.000k = 88
281 measured reflectionsl = 33
271 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.077H 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 reflectionsΔρmax = 0.40 e Å3
41 parametersΔρmin = 0.39 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4937 (6)0.6050 (16)0.735 (3)0.029 (4)*
C20.4085 (6)0.6870 (13)0.634 (4)0.032 (4)*
C30.3404 (5)0.5398 (13)0.629 (4)0.024 (3)*
C40.3647 (6)0.3874 (13)0.437 (5)0.030 (3)*
C50.2993 (6)0.2369 (14)0.458 (3)0.025 (3)*
N10.4205 (5)0.7699 (13)0.366 (3)0.030 (3)*
N20.3023 (5)0.1196 (13)0.254 (3)0.033 (3)*
O10.5533 (4)0.585 (1)0.570 (3)0.037 (3)*
O20.2466 (5)0.232 (1)0.647 (3)0.041 (3)*
O30.4944 (5)0.5602 (11)0.977 (3)0.037 (3)*
H100.39100.78490.75780.0382*
H20.33180.49450.81310.0263*
H30.28410.59490.56290.0263*
H80.42320.34300.49130.0349*
H60.36680.43310.24950.0349*
H50.34700.13400.10910.0405*
H40.26160.01750.24930.0405*
H90.46530.86390.37430.0367*
H10.43790.67730.23180.0367*
H70.36380.82370.30610.0367*
Geometric parameters (Å, º) top
C1—C21.539 (9)C4—H81.000
C1—O11.243 (9)C4—H60.995
C1—O31.250 (9)C5—N21.348 (9)
C2—C31.531 (8)C5—O21.243 (9)
C2—N11.486 (9)N1—H90.993
C2—H100.999N1—H11.003
C3—C41.541 (9)N1—H71.009
C3—H20.987N2—H51.004
C3—H31.018N2—H40.995
C4—C51.525 (8)
C2—C1—O1117.8 (11)C5—C4—H8109.345
C2—C1—O3115.6 (11)C3—C4—H6109.185
O1—C1—O3126.6 (11)C5—C4—H6110.200
C1—C2—C3107.6 (8)H8—C4—H6109.810
C1—C2—N1110.9 (10)C4—C5—N2114.4 (11)
C3—C2—N1112.1 (12)C4—C5—O2120.6 (11)
C1—C2—H10109.133N2—C5—O2124.9 (10)
C3—C2—H10111.217C2—N1—H9110.474
N1—C2—H10105.935C2—N1—H1109.679
C2—C3—C4112.6 (9)H9—N1—H1109.837
C2—C3—H2109.113C2—N1—H7109.025
C4—C3—H2110.368H9—N1—H7109.276
C2—C3—H3107.239H1—N1—H7108.516
C4—C3—H3108.339C5—N2—H5119.622
H2—C3—H3109.039C5—N2—H4120.283
C3—C4—C5110.6 (9)H5—N2—H4120.074
C3—C4—H8107.673
(3.6) top
Crystal data top
C5H10N2O3Dx = 1.710 Mg m3
Mr = 146.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 384 reflections
a = 15.328 (7) Åθ = 2.7–23.1°
b = 7.497 (5) ŵ = 0.14 mm1
c = 4.941 (4) ÅT = 293 K
V = 567.8 (6) Å3Block, colourless
Z = 4not measured × not measured × not measured mm
F(000) = 312.000
Data collection top
Bruker SMART
diffractometer
196 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.144
φ & ω scansθmax = 23.4°, θmin = 2.7°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1716
Tmin = 0.307, Tmax = 1.000k = 88
281 measured reflectionsl = 22
270 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.091H 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 reflectionsΔρmax = 0.53 e Å3
41 parametersΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4949 (7)0.6128 (18)0.733 (3)0.033 (4)*
C20.4084 (6)0.6919 (15)0.637 (4)0.030 (4)*
C30.3396 (6)0.5435 (14)0.630 (5)0.018 (3)*
C40.3644 (7)0.3933 (14)0.432 (5)0.026 (4)*
C50.3005 (7)0.2389 (15)0.468 (3)0.025 (4)*
N10.4184 (6)0.7714 (15)0.363 (4)0.029 (3)*
N20.3014 (6)0.1220 (14)0.262 (3)0.030 (3)*
O10.5543 (5)0.5883 (12)0.566 (4)0.041 (3)*
O20.2478 (5)0.2330 (12)0.657 (3)0.039 (3)*
O30.4952 (5)0.5638 (13)0.975 (3)0.033 (3)*
H100.39000.78740.76560.0369*
H20.33340.49160.81490.0210*
H30.28260.59610.57130.0210*
H80.42510.35160.47030.0311*
H60.36110.43850.24140.0311*
H50.34600.13420.11490.0370*
H40.25780.02320.25540.0370*
H90.46330.86760.36920.0349*
H10.43690.67680.23230.0349*
H70.36120.82250.30390.0349*
Geometric parameters (Å, º) top
C1—C21.528 (9)C4—H80.999
C1—O11.243 (9)C4—H61.004
C1—O31.247 (9)C5—N21.342 (9)
C2—C31.533 (9)C5—O21.238 (9)
C2—N11.49 (1)N1—H90.997
C2—H100.998N1—H11.000
C3—C41.54 (1)N1—H71.001
C3—H20.998N2—H51.001
C3—H31.001N2—H40.998
C4—C51.526 (9)
C2—C1—O1119.0 (12)C5—C4—H8109.824
C2—C1—O3114.6 (12)C3—C4—H6109.670
O1—C1—O3126.1 (13)C5—C4—H6109.337
C1—C2—C3108.8 (10)H8—C4—H6109.219
C1—C2—N1110.5 (11)C4—C5—N2113.7 (11)
C3—C2—N1109.9 (12)C4—C5—O2122.2 (12)
C1—C2—H10108.962N2—C5—O2123.8 (10)
C3—C2—H10109.916C2—N1—H9109.457
N1—C2—H10108.713C2—N1—H1109.391
C2—C3—C4112.1 (10)H9—N1—H1109.696
C2—C3—H2109.164C2—N1—H7109.197
C4—C3—H2108.641H9—N1—H7109.686
C2—C3—H3108.728H1—N1—H7109.398
C4—C3—H3108.637C5—N2—H5119.781
H2—C3—H3109.542C5—N2—H4120.139
C3—C4—C5108.9 (10)H5—N2—H4120.080
C3—C4—H8109.827
(4.9) top
Crystal data top
C5H10N2O3Dx = 1.756 Mg m3
Mr = 146.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 190 reflections
a = 15.191 (8) Åθ = 5.4–22.5°
b = 7.455 (5) ŵ = 0.15 mm1
c = 4.882 (4) ÅT = 293 K
V = 552.8 (6) Å3Block, colourless
Z = 40.00 × 0.00 × 0.00 mm
F(000) = 312.000
Data collection top
Bruker SMART
diffractometer
182 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.214
φ & ω scansθmax = 23.2°, θmin = 2.7°
Absorption correction: multi-scan
SORTAV (Blessing)
h = 1616
Tmin = 0.722, Tmax = 1.000k = 88
292 measured reflectionsl = 33
283 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.114H 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 reflectionsΔρmax = 1.00 e Å3
41 parametersΔρmin = 1.05 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4946 (8)0.619 (2)0.736 (4)0.025 (5)*
C20.4083 (8)0.6962 (17)0.623 (5)0.028 (5)*
C30.3386 (8)0.5471 (16)0.625 (5)0.024 (5)*
C40.3657 (8)0.3955 (16)0.429 (5)0.019 (4)*
C50.2995 (9)0.2424 (18)0.468 (4)0.029 (5)*
N10.4169 (8)0.7804 (18)0.348 (5)0.033 (4)*
N20.3006 (8)0.1232 (18)0.260 (4)0.032 (4)*
O10.5562 (6)0.5959 (14)0.569 (4)0.033 (3)*
O20.2504 (7)0.2316 (14)0.673 (4)0.037 (4)*
O30.4959 (6)0.5678 (16)0.980 (4)0.038 (4)*
H100.38980.79720.74460.0336*
H20.33300.49790.81510.0286*
H30.28070.59780.56580.0286*
H80.42650.35320.47310.0225*
H60.36390.43920.23500.0225*
H50.34190.14090.10220.0389*
H40.26030.01720.26260.0389*
H90.46280.87650.35520.0400*
H10.43450.68730.21120.0400*
H70.35920.83410.29340.0400*
Geometric parameters (Å, º) top
C1—C21.535 (9)C4—H81.000
C1—O11.253 (9)C4—H61.000
C1—O31.252 (9)C5—N21.351 (9)
C2—C31.535 (9)C5—O21.249 (9)
C2—N11.49 (1)N1—H91.000
C2—H101.000N1—H11.000
C3—C41.539 (9)N1—H71.000
C3—H21.000N2—H51.000
C3—H31.000N2—H41.000
C4—C51.534 (9)
C2—C1—O1117.0 (14)C5—C4—H8110.072
C2—C1—O3118.1 (14)C3—C4—H6110.086
O1—C1—O3124.5 (15)C5—C4—H6110.072
C1—C2—C3108.3 (11)H8—C4—H6109.458
C1—C2—N1114.1 (14)C4—C5—N2112.7 (12)
C3—C2—N1112.0 (14)C4—C5—O2122.6 (13)
C1—C2—H10107.961N2—C5—O2124.6 (13)
C3—C2—H10110.293C2—N1—H9109.466
N1—C2—H10104.045C2—N1—H1109.460
C2—C3—C4110.0 (12)H9—N1—H1109.472
C2—C3—H2109.354C2—N1—H7109.470
C4—C3—H2109.341H9—N1—H7109.484
C2—C3—H3109.328H1—N1—H7109.476
C4—C3—H3109.321C5—N2—H5119.996
H2—C3—H3109.472C5—N2—H4120.004
C3—C4—C5107.0 (11)H5—N2—H4120.000
C3—C4—H8110.076
 

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