Effect of pressure on crystalline L- and DL-serine: revisited by a combined single-crystal X-ray diffraction at a laboratory source and polarized Raman spectroscopy study

Information on the effect of pressure on hydrogen bonds, which could be derived from single-crystal X-ray diffraction at a laboratory source and polarized Raman spectroscopy, has been compared. L-Serine and DL-serine were selected for this case study. The role of hydrogen bonds in pressure-induced phase transitions in the first system and in the structural stability of the second one are discussed. Non-monotonic distortion of selected hydrogen bonds in the pressure range below ∼ 1–2 GPa, a change in the compression mechanism at ∼ 2–3 GPa, and the evidence of formation of bifurcated N—H...O hydrogen bonds in DL-serine at ∼ 3–4 GPa are considered.

Computing details

Data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) for DL-serine0.2GPa, DL-serine0.4GPa, DL-serine0.6GPa, DL-serine0.9GPa, DL-serine1.1GPa, DL-serine1.3GPa, DL-serine1.9GPa, DL-serine2.5GPa, DL-serine3.1GPa, DL-serine3.7GPa, DL-serine4.4GPa; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) for L-serine0.1GPa, L-serine0.3GPa, L-serine0.5GPa, L-serine0.8GPa, L-serine1.0GPa, L-serine2.1GPa, L-serine3.1GPa, L-serine4.0GPa, L-serine5.0GPa-phase-II. Cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) for DL-serine0.2GPa, DL-serine0.4GPa, DL-serine0.6GPa, DL-serine0.9GPa, DL-serine1.1GPa, DL-serine1.3GPa, DL-serine1.9GPa, DL-serine2.5GPa, DL-serine3.1GPa, DL-serine3.7GPa, DL-serine4.4GPa; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) for L-serine0.1GPa, L-serine0.3GPa, L-serine0.5GPa, L-serine0.8GPa, L-serine1.0GPa, L-serine2.1GPa, L-serine3.1GPa, L-serine4.0GPa, L-serine5.0GPa-phase-II. Data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) for DL-serine0.2GPa, DL-serine0.4GPa, DL-serine0.6GPa, DL-serine0.9GPa, DL-serine1.1GPa, DL-serine1.3GPa, DL-serine1.9GPa, DL-serine2.5GPa, DL-serine3.1GPa, DL-serine3.7GPa, DL-serine4.4GPa; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) for L-serine0.1GPa, L-serine0.3GPa, L-serine0.5GPa, L-serine0.8GPa, L-serine1.0GPa, L-serine2.1GPa, L-serine3.1GPa, L-serine4.0GPa, L-serine5.0GPa-phase-II. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006), PLATON (Spek, 2009), enCIFer (Allen et al., 2004).

Figures

(DL-serine0.2GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.576 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8431 (5) Å	Cell parameters from 2039 reflections
b = 9.0258 (5) Å	θ = 2.3–31.0°
c = 10.319 (9) Å	µ = 0.14 mm^−1
β = 100.86 (3)°	T = 293 K
V = 443.0 (4) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	368 independent reflections
Radiation source: Enhance (Mo) X-ray Source	295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
rotation method scans	θmax = 31.1°, θmin = 4.4°
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	h = −7→7
Tmin = 0.397, Tmax = 0.474	k = −13→13
3890 measured reflections	l = −5→5

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0425P)^2] where P = (Fo^2 + 2Fc^2)/3
368 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.11 e Å^−3
55 restraints	Δρmin = −0.08 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2629 (2)	0.39185 (10)	0.3320 (3)	0.034 (2)
O2	0.3077 (3)	0.15597 (11)	0.0640 (3)	0.039 (2)
H2	0.2769	0.0751	0.0946	0.047*
N1	0.5994 (3)	0.16188 (13)	0.3522 (4)	0.026 (2)
H1A	0.4308	0.1192	0.3348	0.031*
H1B	0.6200	0.2095	0.4289	0.031*
H1C	0.7321	0.0928	0.3567	0.031*
O3	0.4121 (2)	0.49482 (11)	0.1614 (3)	0.036 (2)
C1	0.6251 (3)	0.26924 (16)	0.2453 (5)	0.029 (2)
H1	0.8144	0.3120	0.2654	0.035*
C2	0.4129 (3)	0.39606 (14)	0.2474 (4)	0.025 (3)
C3	0.5902 (4)	0.1975 (2)	0.1125 (7)	0.031 (3)
H3A	0.6511	0.2657	0.0509	0.038*
H3B	0.7089	0.1102	0.1185	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0275 (6)	0.0277 (5)	0.050 (7)	0.0024 (4)	0.0169 (18)	0.0001 (10)
O2	0.0371 (7)	0.0275 (5)	0.047 (7)	−0.0079 (4)	−0.0050 (16)	0.0047 (11)
N1	0.0239 (7)	0.0220 (6)	0.030 (8)	0.0022 (4)	0.003 (2)	−0.0041 (12)
O3	0.0329 (7)	0.0246 (5)	0.053 (7)	0.0009 (4)	0.0123 (19)	0.0094 (10)
C1	0.0174 (8)	0.0207 (7)	0.050 (7)	−0.0009 (5)	0.0099 (19)	−0.0020 (15)
C2	0.0179 (8)	0.0183 (6)	0.038 (8)	−0.0035 (5)	0.003 (2)	−0.0034 (13)
C3	0.0276 (10)	0.0284 (7)	0.038 (8)	0.0011 (6)	0.006 (2)	−0.0063 (18)

Geometric parameters (Å, º)

O1—C2	1.236 (4)	O3—C2	1.257 (4)
O2—C3	1.416 (3)	C1—C3	1.496 (9)
O2—H2	0.8200	C1—C2	1.541 (2)
N1—C1	1.491 (5)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	C3—C1—H1	107.7
C1—N1—H1A	109.5	C2—C1—H1	107.7
C1—N1—H1B	109.5	O1—C2—O3	126.57 (14)
H1A—N1—H1B	109.5	O1—C2—C1	118.0 (3)
C1—N1—H1C	109.5	O3—C2—C1	115.4 (3)
H1A—N1—H1C	109.5	O2—C3—C1	111.9 (3)
H1B—N1—H1C	109.5	O2—C3—H3A	109.2
N1—C1—C3	112.68 (19)	C1—C3—H3A	109.2
N1—C1—C2	108.8 (3)	O2—C3—H3B	109.2
C3—C1—C2	112.0 (4)	C1—C3—H3B	109.2
N1—C1—H1	107.7	H3A—C3—H3B	107.9
N1—C1—C2—O1	0.4 (4)	C3—C1—C2—O3	−54.6 (3)
C3—C1—C2—O1	125.7 (3)	N1—C1—C3—O2	72.0 (3)
N1—C1—C2—O3	−179.9 (2)	C2—C1—C3—O2	−51.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.94	2.769 (5)	154
N1—H1A···O3^ii	0.89	2.01	2.8809 (15)	165
N1—H1C···O3^iii	0.89	1.98	2.8311 (14)	160
O2—H2···O1^ii	0.82	1.84	2.663 (2)	176

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine0.4GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.595 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8424 (6) Å	Cell parameters from 1785 reflections
b = 8.9832 (6) Å	θ = 4.3–31.0°
c = 10.250 (11) Å	µ = 0.14 mm^−1
β = 101.03 (4)°	T = 293 K
V = 437.6 (5) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	372 independent reflections
Radiation source: Enhance (Mo) X-ray Source	313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
rotation method scans	θmax = 31.1°, θmin = 4.4°
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	h = −7→7
Tmin = 0.399, Tmax = 0.473	k = −13→13
3587 measured reflections	l = −5→5

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 0.0295P] where P = (Fo^2 + 2Fc^2)/3
372 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.12 e Å^−3
55 restraints	Δρmin = −0.11 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2618 (3)	0.38859 (12)	0.3312 (4)	0.041 (2)
O2	0.3110 (3)	0.15198 (13)	0.0623 (4)	0.037 (2)
H2	0.2815	0.0693	0.0906	0.044*
N1	0.6018 (3)	0.15883 (14)	0.3551 (4)	0.030 (3)
H1A	0.4342	0.1148	0.3374	0.036*
H1B	0.6204	0.2076	0.4319	0.036*
H1C	0.7363	0.0903	0.3609	0.036*
O3	0.4086 (3)	0.49123 (13)	0.1587 (4)	0.043 (3)
C1	0.6268 (4)	0.26675 (18)	0.2456 (6)	0.032 (2)
H1	0.8152	0.3108	0.2660	0.038*
C2	0.4115 (3)	0.39286 (16)	0.2456 (5)	0.027 (3)
C3	0.5932 (4)	0.1939 (2)	0.1126 (8)	0.034 (3)
H3A	0.6554	0.2619	0.0506	0.041*
H3B	0.7120	0.1062	0.1197	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0267 (7)	0.0258 (5)	0.074 (7)	0.0023 (5)	0.0189 (19)	−0.0016 (11)
O2	0.0379 (8)	0.0261 (5)	0.042 (8)	−0.0069 (5)	−0.0029 (18)	0.0051 (12)
N1	0.0240 (8)	0.0213 (6)	0.046 (8)	0.0024 (5)	0.012 (2)	−0.0046 (13)
O3	0.0303 (7)	0.0241 (6)	0.077 (8)	0.0016 (4)	0.017 (2)	0.0070 (11)
C1	0.0198 (8)	0.0196 (7)	0.058 (7)	−0.0016 (5)	0.0133 (19)	−0.0038 (16)
C2	0.0177 (8)	0.0168 (7)	0.045 (9)	−0.0026 (5)	0.004 (2)	−0.0024 (15)
C3	0.0247 (10)	0.0281 (8)	0.050 (8)	0.0016 (7)	0.007 (2)	−0.006 (2)

Geometric parameters (Å, º)

O1—C2	1.241 (4)	O3—C2	1.253 (5)
O2—C3	1.416 (4)	C1—C3	1.493 (9)
O2—H2	0.8200	C1—C2	1.540 (2)
N1—C1	1.506 (6)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	107.8
C1—N1—H1A	109.5	C2—C1—H1	107.8
C1—N1—H1B	109.5	O1—C2—O3	126.59 (16)
H1A—N1—H1B	109.5	O1—C2—C1	117.7 (3)
C1—N1—H1C	109.5	O3—C2—C1	115.7 (3)
H1A—N1—H1C	109.5	O2—C3—C1	112.2 (3)
H1B—N1—H1C	109.5	O2—C3—H3A	109.2
C3—C1—N1	112.9 (2)	C1—C3—H3A	109.2
C3—C1—C2	111.6 (4)	O2—C3—H3B	109.2
N1—C1—C2	108.8 (3)	C1—C3—H3B	109.2
C3—C1—H1	107.8	H3A—C3—H3B	107.9
C3—C1—C2—O1	126.1 (4)	N1—C1—C2—O3	−179.9 (3)
N1—C1—C2—O1	0.9 (4)	N1—C1—C3—O2	72.5 (3)
C3—C1—C2—O3	−54.7 (3)	C2—C1—C3—O2	−50.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.94	2.757 (5)	152
N1—H1A···O3^ii	0.89	2.00	2.8747 (17)	166
N1—H1C···O3^iii	0.89	1.98	2.8345 (16)	161
O2—H2···O1^ii	0.82	1.84	2.657 (3)	175

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine0.6GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.617 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8307 (12) Å	Cell parameters from 906 reflections
b = 8.956 (2) Å	θ = 3.1–30.6°
c = 10.175 (10) Å	µ = 0.15 mm^−1
β = 101.33 (5)°	T = 293 K
V = 431.6 (4) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	438 independent reflections
Radiation source: Enhance (Mo) X-ray Source	277 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 10.3457 pixels mm^-1	θmax = 30.6°, θmin = 3.1°
rotation method scans	h = −6→6
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −11→12
Tmin = 0.400, Tmax = 0.473	l = −7→8
1715 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.047	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0209P)^2] where P = (Fo^2 + 2Fc^2)/3
438 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.13 e Å^−3
55 restraints	Δρmin = −0.09 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2612 (2)	0.38672 (10)	0.33126 (19)	0.0284 (7)
O2	0.3135 (3)	0.15019 (11)	0.06104 (18)	0.0306 (8)
H2	0.2907	0.0621	0.0782	0.037*
N1	0.6043 (3)	0.15761 (13)	0.3555 (2)	0.0257 (9)
H1A	0.4368	0.1127	0.3371	0.031*
H1B	0.6221	0.2062	0.4331	0.031*
H1C	0.7404	0.0895	0.3614	0.031*
O3	0.4071 (2)	0.48960 (11)	0.15740 (19)	0.0314 (7)
C1	0.6272 (4)	0.26609 (17)	0.2462 (3)	0.0214 (10)
H1	0.8159	0.3108	0.2672	0.026*
C2	0.4133 (4)	0.39058 (17)	0.2464 (3)	0.0225 (10)
C3	0.5962 (4)	0.19164 (19)	0.1129 (3)	0.0243 (11)
H3A	0.6605	0.2590	0.0504	0.029*
H3B	0.7146	0.1033	0.1216	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0294 (7)	0.0268 (6)	0.032 (2)	0.0049 (6)	0.0136 (11)	0.0005 (6)
O2	0.0382 (8)	0.0241 (8)	0.025 (3)	−0.0071 (6)	−0.0051 (12)	0.0030 (6)
N1	0.0274 (9)	0.0214 (7)	0.030 (3)	0.0032 (7)	0.0083 (14)	−0.0005 (8)
O3	0.0295 (8)	0.0262 (7)	0.039 (2)	0.0009 (6)	0.0087 (11)	0.0097 (8)
C1	0.0180 (10)	0.0225 (10)	0.025 (4)	0.0020 (8)	0.0068 (15)	0.0015 (10)
C2	0.0176 (9)	0.0185 (9)	0.030 (4)	−0.0052 (8)	0.0018 (15)	−0.0027 (10)
C3	0.0256 (10)	0.0291 (10)	0.018 (4)	0.0011 (8)	0.0035 (16)	0.0001 (10)

Geometric parameters (Å, º)

O1—C2	1.239 (3)	O3—C2	1.264 (3)
O2—C3	1.413 (3)	C1—C3	1.492 (5)
O2—H2	0.8200	C1—C2	1.520 (2)
N1—C1	1.498 (4)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	107.7
C1—N1—H1A	109.5	C2—C1—H1	107.7
C1—N1—H1B	109.5	O1—C2—O3	125.82 (16)
H1A—N1—H1B	109.5	O1—C2—C1	118.47 (19)
C1—N1—H1C	109.5	O3—C2—C1	115.70 (19)
H1A—N1—H1C	109.5	O2—C3—C1	111.93 (17)
H1B—N1—H1C	109.5	O2—C3—H3A	109.2
C3—C1—N1	112.12 (16)	C1—C3—H3A	109.2
C3—C1—C2	112.5 (3)	O2—C3—H3B	109.2
N1—C1—C2	108.97 (18)	C1—C3—H3B	109.2
C3—C1—H1	107.7	H3A—C3—H3B	107.9
C3—C1—C2—O1	125.5 (2)	N1—C1—C2—O3	−179.1 (2)
N1—C1—C2—O1	0.5 (3)	N1—C1—C3—O2	73.7 (3)
C3—C1—C2—O3	−54.2 (3)	C2—C1—C3—O2	−49.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.93	2.743 (3)	151
N1—H1A···O3^ii	0.89	2.00	2.8734 (17)	165
N1—H1C···O3^iii	0.89	1.97	2.8239 (16)	161
O2—H2···O1^ii	0.82	1.86	2.6560 (16)	162

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine0.9GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.631 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8361 (5) Å	Cell parameters from 2084 reflections
b = 8.9202 (6) Å	θ = 2.3–31.1°
c = 10.123 (8) Å	µ = 0.15 mm^−1
β = 101.49 (3)°	T = 293 K
V = 427.9 (3) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	442 independent reflections
Radiation source: Enhance (Mo) X-ray Source	364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.1°, θmin = 4.4°
rotation method scans	h = −6→7
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.393, Tmax = 0.472	l = −5→5
3825 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0407P)^2] where P = (Fo^2 + 2Fc^2)/3
442 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.12 e Å^−3
55 restraints	Δρmin = −0.12 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2606 (2)	0.38468 (10)	0.3309 (3)	0.0253 (15)
O2	0.3162 (3)	0.14708 (11)	0.0600 (3)	0.0322 (15)
H2	0.2845	0.0653	0.0909	0.039*
N1	0.6054 (2)	0.15549 (12)	0.3561 (3)	0.0195 (16)
H1A	0.4368	0.1116	0.3379	0.023*
H1B	0.6257	0.2042	0.4342	0.023*
H1C	0.7395	0.0861	0.3616	0.023*
O3	0.4041 (2)	0.48700 (11)	0.1561 (3)	0.0310 (15)
C1	0.6291 (3)	0.26347 (15)	0.2467 (4)	0.0193 (16)
H1	0.8174	0.3088	0.2683	0.023*
C2	0.4115 (3)	0.38880 (14)	0.2450 (4)	0.0219 (18)
C3	0.5979 (3)	0.18985 (16)	0.1132 (5)	0.0277 (18)
H3A	0.6614	0.2581	0.0508	0.033*
H3B	0.7175	0.1017	0.1217	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0245 (5)	0.0260 (5)	0.028 (5)	0.0022 (4)	0.0120 (13)	−0.0019 (8)
O2	0.0359 (6)	0.0235 (5)	0.033 (5)	−0.0055 (4)	−0.0036 (12)	0.0039 (8)
N1	0.0207 (6)	0.0199 (6)	0.016 (5)	0.0023 (4)	−0.0010 (14)	−0.0075 (9)
O3	0.0284 (6)	0.0224 (5)	0.043 (5)	0.0021 (4)	0.0084 (12)	0.0076 (9)
C1	0.0151 (6)	0.0205 (6)	0.022 (5)	−0.0010 (4)	0.0040 (14)	−0.0019 (12)
C2	0.0157 (6)	0.0171 (6)	0.032 (6)	−0.0029 (4)	0.0026 (15)	−0.0017 (11)
C3	0.0248 (8)	0.0255 (7)	0.033 (6)	0.0021 (5)	0.0057 (16)	−0.0041 (14)

Geometric parameters (Å, º)

O1—C2	1.242 (3)	O3—C2	1.252 (4)
O2—C3	1.414 (3)	C1—C3	1.483 (7)
O2—H2	0.8200	C1—C2	1.5331 (18)
N1—C1	1.489 (4)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	107.9
C1—N1—H1A	109.5	C2—C1—H1	107.9
C1—N1—H1B	109.5	O1—C2—O3	125.98 (14)
H1A—N1—H1B	109.5	O1—C2—C1	117.9 (2)
C1—N1—H1C	109.5	O3—C2—C1	116.1 (2)
H1A—N1—H1C	109.5	O2—C3—C1	112.5 (2)
H1B—N1—H1C	109.5	O2—C3—H3A	109.1
C3—C1—N1	112.48 (15)	C1—C3—H3A	109.1
C3—C1—C2	111.6 (3)	O2—C3—H3B	109.1
N1—C1—C2	109.0 (2)	C1—C3—H3B	109.1
C3—C1—H1	107.9	H3A—C3—H3B	107.8
C3—C1—C2—O1	126.2 (3)	N1—C1—C2—O3	−178.9 (2)
N1—C1—C2—O1	1.4 (3)	N1—C1—C3—O2	73.1 (2)
C3—C1—C2—O3	−54.0 (2)	C2—C1—C3—O2	−49.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.94	2.750 (3)	151
N1—H1A···O3^ii	0.89	2.00	2.8679 (13)	165
N1—H1C···O3^iii	0.89	1.98	2.8314 (13)	161
O2—H2···O1^ii	0.82	1.83	2.646 (2)	176

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine1.1GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.640 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8329 (5) Å	Cell parameters from 1788 reflections
b = 8.9119 (6) Å	θ = 2.3–31.0°
c = 10.088 (7) Å	µ = 0.15 mm^−1
β = 101.58 (3)°	T = 293 K
V = 425.6 (3) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	438 independent reflections
Radiation source: Enhance (Mo) X-ray Source	349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.1°, θmin = 4.4°
rotation method scans	h = −7→6
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.396, Tmax = 0.473	l = −5→5
3353 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0359P)^2] where P = (Fo^2 + 2Fc^2)/3
438 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.11 e Å^−3
55 restraints	Δρmin = −0.11 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2604 (2)	0.38361 (9)	0.3309 (3)	0.0266 (14)
O2	0.3171 (2)	0.14567 (11)	0.0596 (3)	0.0329 (15)
H2	0.2830	0.0658	0.0934	0.039*
N1	0.6066 (3)	0.15420 (11)	0.3565 (3)	0.0193 (17)
H1A	0.4366	0.1116	0.3388	0.023*
H1B	0.6303	0.2025	0.4352	0.023*
H1C	0.7387	0.0838	0.3610	0.023*
O3	0.4028 (2)	0.48565 (10)	0.1551 (3)	0.0296 (15)
C1	0.6302 (3)	0.26216 (15)	0.2473 (4)	0.0226 (17)
H1	0.8184	0.3077	0.2693	0.027*
C2	0.4112 (3)	0.38760 (14)	0.2455 (4)	0.0235 (18)
C3	0.6000 (3)	0.18848 (16)	0.1134 (5)	0.0245 (18)
H3A	0.6639	0.2568	0.0509	0.029*
H3B	0.7197	0.1002	0.1222	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0235 (5)	0.0243 (5)	0.036 (5)	0.0014 (4)	0.0149 (12)	−0.0006 (7)
O2	0.0355 (6)	0.0215 (5)	0.039 (5)	−0.0057 (4)	0.0003 (12)	0.0043 (8)
N1	0.0209 (6)	0.0205 (6)	0.016 (5)	0.0005 (4)	0.0023 (15)	−0.0061 (9)
O3	0.0278 (6)	0.0224 (5)	0.040 (5)	0.0020 (4)	0.0094 (12)	0.0082 (8)
C1	0.0140 (6)	0.0184 (6)	0.036 (5)	−0.0003 (4)	0.0056 (14)	−0.0013 (11)
C2	0.0154 (7)	0.0163 (6)	0.039 (6)	−0.0025 (4)	0.0048 (16)	−0.0025 (10)
C3	0.0265 (8)	0.0249 (7)	0.023 (6)	0.0027 (5)	0.0070 (17)	−0.0026 (13)

Geometric parameters (Å, º)

O1—C2	1.236 (3)	O3—C2	1.258 (4)
O2—C3	1.418 (3)	C1—C3	1.482 (6)
O2—H2	0.8200	C1—C2	1.5370 (19)
N1—C1	1.484 (4)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	107.9
C1—N1—H1A	109.5	C2—C1—H1	107.9
C1—N1—H1B	109.5	O1—C2—O3	126.00 (14)
H1A—N1—H1B	109.5	O1—C2—C1	118.2 (2)
C1—N1—H1C	109.5	O3—C2—C1	115.8 (3)
H1A—N1—H1C	109.5	O2—C3—C1	112.3 (2)
H1B—N1—H1C	109.5	O2—C3—H3A	109.2
C3—C1—N1	112.39 (15)	C1—C3—H3A	109.2
C3—C1—C2	111.7 (3)	O2—C3—H3B	109.2
N1—C1—C2	108.9 (2)	C1—C3—H3B	109.2
C3—C1—H1	107.9	H3A—C3—H3B	107.9
C3—C1—C2—O1	126.2 (3)	N1—C1—C2—O3	−178.3 (2)
N1—C1—C2—O1	1.4 (3)	N1—C1—C3—O2	73.3 (2)
C3—C1—C2—O3	−53.5 (2)	C2—C1—C3—O2	−49.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.94	2.753 (4)	151
N1—H1A···O3^ii	0.89	2.00	2.8663 (13)	165
N1—H1C···O3^iii	0.89	1.98	2.8289 (13)	160
O2—H2···O1^ii	0.82	1.82	2.642 (2)	175

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine1.3GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.648 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8235 (5) Å	Cell parameters from 2027 reflections
b = 8.8863 (6) Å	θ = 2.3–31.2°
c = 10.094 (8) Å	µ = 0.15 mm^−1
β = 101.69 (3)°	T = 293 K
V = 423.7 (4) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	435 independent reflections
Radiation source: Enhance (Mo) X-ray Source	369 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.2°, θmin = 4.6°
rotation method scans	h = −7→6
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.395, Tmax = 0.472	l = −5→5
3981 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 0.0194P] where P = (Fo^2 + 2Fc^2)/3
435 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.11 e Å^−3
55 restraints	Δρmin = −0.10 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2605 (2)	0.38222 (10)	0.3317 (3)	0.0280 (15)
O2	0.3189 (3)	0.14426 (11)	0.0582 (3)	0.0323 (15)
H2	0.2864	0.0628	0.0900	0.039*
N1	0.6077 (3)	0.15330 (12)	0.3571 (3)	0.0179 (17)
H1A	0.4375	0.1104	0.3392	0.022*
H1B	0.6310	0.2018	0.4357	0.022*
H1C	0.7404	0.0828	0.3619	0.022*
O3	0.4014 (2)	0.48474 (11)	0.1536 (3)	0.0281 (15)
C1	0.6316 (3)	0.26134 (15)	0.2481 (5)	0.0203 (17)
H1	0.8197	0.3076	0.2706	0.024*
C2	0.4103 (3)	0.38671 (14)	0.2439 (4)	0.0203 (19)
C3	0.6021 (3)	0.18782 (16)	0.1130 (5)	0.0235 (19)
H3A	0.6659	0.2570	0.0510	0.028*
H3B	0.7228	0.0996	0.1216	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0232 (5)	0.0258 (5)	0.038 (5)	0.0015 (4)	0.0142 (13)	−0.0019 (8)
O2	0.0354 (6)	0.0216 (5)	0.036 (5)	−0.0053 (4)	−0.0025 (12)	0.0043 (8)
N1	0.0206 (6)	0.0206 (6)	0.011 (6)	0.0010 (4)	0.0004 (15)	−0.0058 (9)
O3	0.0280 (6)	0.0221 (5)	0.035 (5)	0.0017 (3)	0.0081 (12)	0.0087 (8)
C1	0.0151 (6)	0.0195 (6)	0.027 (5)	−0.0016 (5)	0.0047 (14)	−0.0031 (12)
C2	0.0158 (7)	0.0169 (6)	0.027 (6)	−0.0027 (4)	0.0024 (16)	−0.0025 (11)
C3	0.0257 (8)	0.0236 (7)	0.021 (6)	0.0024 (5)	0.0057 (17)	−0.0019 (14)

Geometric parameters (Å, º)

O1—C2	1.253 (4)	O3—C2	1.255 (4)
O2—C3	1.420 (3)	C1—C3	1.493 (7)
O2—H2	0.8200	C1—C2	1.5374 (18)
N1—C1	1.482 (4)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	C3—C1—H1	107.9
C1—N1—H1A	109.5	C2—C1—H1	107.9
C1—N1—H1B	109.5	O1—C2—O3	126.61 (13)
H1A—N1—H1B	109.5	O1—C2—C1	117.0 (3)
C1—N1—H1C	109.5	O3—C2—C1	116.4 (3)
H1A—N1—H1C	109.5	O2—C3—C1	112.4 (2)
H1B—N1—H1C	109.5	O2—C3—H3A	109.1
N1—C1—C3	112.80 (15)	C1—C3—H3A	109.1
N1—C1—C2	109.4 (2)	O2—C3—H3B	109.1
C3—C1—C2	110.8 (3)	C1—C3—H3B	109.1
N1—C1—H1	107.9	H3A—C3—H3B	107.9
N1—C1—C2—O1	2.8 (3)	C3—C1—C2—O3	−53.3 (2)
C3—C1—C2—O1	127.8 (3)	N1—C1—C3—O2	73.1 (2)
N1—C1—C2—O3	−178.3 (2)	C2—C1—C3—O2	−50.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.94	2.749 (4)	150
N1—H1A···O3^ii	0.89	1.99	2.8598 (14)	164
N1—H1C···O3^iii	0.89	1.97	2.8222 (13)	160
O2—H2···O1^ii	0.82	1.82	2.641 (2)	176

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine1.9GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.683 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8098 (4) Å	Cell parameters from 1666 reflections
b = 8.8377 (5) Å	θ = 2.3–30.6°
c = 9.971 (8) Å	µ = 0.15 mm^−1
β = 101.94 (3)°	T = 293 K
V = 414.7 (3) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	413 independent reflections
Radiation source: Enhance (Mo) X-ray Source	350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 10.3457 pixels mm^-1	θmax = 30.7°, θmin = 4.4°
rotation method scans	h = −6→6
Absorption correction: GAUSSIAN Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.394, Tmax = 0.473	l = −5→5
3261 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.0016P] where P = (Fo^2 + 2Fc^2)/3
413 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.14 e Å^−3
55 restraints	Δρmin = −0.11 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2601 (3)	0.38042 (11)	0.3321 (3)	0.0254 (19)
O2	0.3225 (3)	0.14199 (13)	0.0563 (4)	0.0293 (19)
H2	0.2852	0.0641	0.0938	0.035*
N1	0.6105 (3)	0.15132 (14)	0.3595 (4)	0.020 (2)
H1A	0.4413	0.1064	0.3397	0.024*
H1B	0.6292	0.2003	0.4389	0.024*
H1C	0.7465	0.0818	0.3660	0.024*
O3	0.3985 (3)	0.48290 (12)	0.1526 (3)	0.0226 (18)
C1	0.6345 (3)	0.25999 (17)	0.2498 (5)	0.0220 (19)
H1	0.8226	0.3073	0.2733	0.026*
C2	0.4102 (3)	0.38491 (15)	0.2438 (5)	0.020 (2)
C3	0.6067 (4)	0.18653 (18)	0.1132 (6)	0.027 (2)
H3A	0.6708	0.2564	0.0510	0.032*
H3B	0.7288	0.0981	0.1223	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0218 (6)	0.0252 (6)	0.032 (6)	0.0016 (4)	0.0122 (15)	−0.0008 (9)
O2	0.0336 (7)	0.0209 (5)	0.029 (6)	−0.0046 (4)	−0.0034 (15)	0.0033 (9)
N1	0.0198 (7)	0.0193 (6)	0.021 (6)	0.0018 (5)	0.0041 (17)	−0.0046 (11)
O3	0.0257 (7)	0.0216 (6)	0.021 (6)	0.0014 (4)	0.0055 (15)	0.0062 (9)
C1	0.0147 (7)	0.0172 (7)	0.034 (6)	−0.0009 (5)	0.0057 (17)	−0.0034 (14)
C2	0.0159 (8)	0.0152 (7)	0.030 (7)	−0.0039 (5)	0.0045 (18)	−0.0060 (12)
C3	0.0245 (9)	0.0222 (8)	0.035 (7)	0.0020 (6)	0.009 (2)	−0.0030 (16)

Geometric parameters (Å, º)

O1—C2	1.249 (4)	O3—C2	1.249 (4)
O2—C3	1.423 (3)	C1—C3	1.489 (8)
O2—H2	0.8200	C1—C2	1.536 (2)
N1—C1	1.479 (5)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	C3—C1—H1	108.0
C1—N1—H1A	109.5	C2—C1—H1	108.0
C1—N1—H1B	109.5	O3—C2—O1	126.14 (15)
H1A—N1—H1B	109.5	O3—C2—C1	116.9 (3)
C1—N1—H1C	109.5	O1—C2—C1	117.0 (3)
H1A—N1—H1C	109.5	O2—C3—C1	112.5 (2)
H1B—N1—H1C	109.5	O2—C3—H3A	109.1
N1—C1—C3	112.80 (18)	C1—C3—H3A	109.1
N1—C1—C2	109.5 (3)	O2—C3—H3B	109.1
C3—C1—C2	110.4 (3)	C1—C3—H3B	109.1
N1—C1—H1	108.0	H3A—C3—H3B	107.8
N1—C1—C2—O3	−177.8 (3)	C3—C1—C2—O1	128.2 (3)
C3—C1—C2—O3	−53.0 (3)	N1—C1—C3—O2	73.0 (3)
N1—C1—C2—O1	3.4 (4)	C2—C1—C3—O2	−49.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.93	2.720 (4)	147
N1—H1A···O3^ii	0.89	1.98	2.8462 (15)	164
N1—H1C···O3^iii	0.89	1.96	2.8153 (16)	160
O2—H2···O1^ii	0.82	1.82	2.631 (2)	173

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine2.5GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.710 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.7926 (5) Å	Cell parameters from 1979 reflections
b = 8.7932 (5) Å	θ = 2.3–30.8°
c = 9.907 (9) Å	µ = 0.15 mm^−1
β = 102.14 (4)°	T = 293 K
V = 408.1 (4) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	389 independent reflections
Radiation source: Enhance (Mo) X-ray Source	329 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 10.3457 pixels mm^-1	θmax = 30.7°, θmin = 4.4°
rotation method scans	h = −6→6
Absorption correction: GAUSSIAN Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.394, Tmax = 0.474	l = −5→5
3895 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0368P)^2 + 0.048P] where P = (Fo^2 + 2Fc^2)/3
389 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.13 e Å^−3
55 restraints	Δρmin = −0.11 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2597 (3)	0.37907 (11)	0.3323 (4)	0.024 (2)
O2	0.3263 (3)	0.14077 (12)	0.0551 (4)	0.026 (2)
H2	0.2892	0.0615	0.0912	0.032*
N1	0.6122 (3)	0.14957 (14)	0.3603 (5)	0.019 (2)
H1A	0.4407	0.1061	0.3412	0.023*
H1B	0.6351	0.1986	0.4405	0.023*
H1C	0.7462	0.0784	0.3659	0.023*
O3	0.3963 (3)	0.48155 (13)	0.1517 (4)	0.022 (2)
C1	0.6365 (4)	0.25905 (18)	0.2492 (6)	0.020 (2)
H1	0.8250	0.3071	0.2736	0.024*
C2	0.4100 (4)	0.38391 (16)	0.2433 (5)	0.018 (2)
C3	0.6116 (4)	0.1860 (2)	0.1146 (7)	0.024 (2)
H3A	0.6776	0.2560	0.0523	0.029*
H3B	0.7344	0.0972	0.1249	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0217 (6)	0.0231 (6)	0.030 (6)	0.0018 (4)	0.0134 (16)	0.0008 (10)
O2	0.0315 (7)	0.0192 (5)	0.023 (7)	−0.0041 (4)	−0.0058 (16)	0.0045 (10)
N1	0.0181 (7)	0.0190 (6)	0.018 (7)	0.0013 (5)	0.001 (2)	−0.0061 (12)
O3	0.0245 (7)	0.0205 (6)	0.020 (6)	0.0015 (4)	0.0045 (17)	0.0053 (11)
C1	0.0136 (8)	0.0172 (7)	0.030 (6)	−0.0012 (6)	0.0050 (18)	−0.0041 (16)
C2	0.0137 (8)	0.0155 (7)	0.024 (8)	−0.0046 (5)	0.002 (2)	−0.0074 (14)
C3	0.0230 (9)	0.0213 (8)	0.027 (7)	0.0039 (6)	0.005 (2)	0.0003 (19)

Geometric parameters (Å, º)

O1—C2	1.251 (4)	O3—C2	1.242 (5)
O2—C3	1.427 (4)	C1—C3	1.462 (8)
O2—H2	0.8200	C1—C2	1.536 (2)
N1—C1	1.485 (5)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	108.0
C1—N1—H1A	109.5	C2—C1—H1	108.0
C1—N1—H1B	109.5	O3—C2—O1	126.11 (16)
H1A—N1—H1B	109.5	O3—C2—C1	116.7 (3)
C1—N1—H1C	109.5	O1—C2—C1	117.1 (3)
H1A—N1—H1C	109.5	O2—C3—C1	112.7 (3)
H1B—N1—H1C	109.5	O2—C3—H3A	109.0
C3—C1—N1	112.8 (2)	C1—C3—H3A	109.0
C3—C1—C2	111.0 (4)	O2—C3—H3B	109.0
N1—C1—C2	109.0 (3)	C1—C3—H3B	109.0
C3—C1—H1	108.0	H3A—C3—H3B	107.8
C3—C1—C2—O3	−52.6 (3)	N1—C1—C2—O1	3.6 (4)
N1—C1—C2—O3	−177.4 (3)	N1—C1—C3—O2	73.5 (3)
C3—C1—C2—O1	128.4 (3)	C2—C1—C3—O2	−49.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.92	2.710 (4)	147
N1—H1A···O3^ii	0.89	1.97	2.8310 (16)	164
N1—H1C···O3^iii	0.89	1.95	2.8041 (16)	159
O2—H2···O1^ii	0.82	1.81	2.627 (3)	174

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine3.1GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.736 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.7708 (6) Å	Cell parameters from 1919 reflections
b = 8.7429 (7) Å	θ = 2.3–30.8°
c = 9.864 (11) Å	µ = 0.16 mm^−1
β = 102.14 (4)°	T = 293 K
V = 402.2 (5) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	360 independent reflections
Radiation source: Enhance (Mo) X-ray Source	312 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 10.3457 pixels mm^-1	θmax = 30.8°, θmin = 4.4°
rotation method scans	h = −6→6
Absorption correction: GAUSSIAN Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.393, Tmax = 0.474	l = −4→4
3631 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0504P)^2] where P = (Fo^2 + 2Fc^2)/3
360 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.13 e Å^−3
55 restraints	Δρmin = −0.11 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2598 (2)	0.37812 (10)	0.3333 (3)	0.024 (2)
O2	0.3297 (3)	0.13995 (11)	0.0546 (4)	0.025 (2)
H2	0.2919	0.0604	0.0910	0.030*
N1	0.6138 (3)	0.14850 (13)	0.3610 (4)	0.019 (2)
H1A	0.4401	0.1063	0.3425	0.023*
H1B	0.6403	0.1974	0.4419	0.023*
H1C	0.7459	0.0758	0.3654	0.023*
O3	0.3941 (3)	0.48063 (12)	0.1505 (3)	0.022 (2)
C1	0.6388 (3)	0.25871 (17)	0.2496 (5)	0.024 (2)
H1	0.8275	0.3076	0.2746	0.028*
C2	0.4106 (3)	0.38274 (14)	0.2443 (5)	0.020 (2)
C3	0.6163 (4)	0.18562 (18)	0.1151 (6)	0.027 (2)
H3A	0.6833	0.2561	0.0528	0.033*
H3B	0.7399	0.0964	0.1258	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0214 (6)	0.0243 (6)	0.030 (6)	0.0004 (4)	0.0156 (16)	−0.0023 (9)
O2	0.0319 (7)	0.0188 (5)	0.021 (7)	−0.0040 (4)	−0.0035 (16)	0.0026 (9)
N1	0.0177 (7)	0.0186 (5)	0.021 (7)	0.0021 (4)	0.0030 (19)	−0.0026 (11)
O3	0.0240 (7)	0.0195 (5)	0.022 (6)	0.0018 (4)	0.0053 (16)	0.0042 (10)
C1	0.0154 (7)	0.0165 (6)	0.041 (6)	0.0003 (5)	0.0095 (18)	−0.0009 (15)
C2	0.0136 (7)	0.0135 (6)	0.033 (8)	−0.0035 (4)	0.003 (2)	−0.0036 (13)
C3	0.0250 (9)	0.0196 (7)	0.039 (7)	0.0042 (6)	0.009 (2)	−0.0020 (18)

Geometric parameters (Å, º)

O1—C2	1.248 (4)	O3—C2	1.250 (5)
O2—C3	1.429 (3)	C1—C3	1.456 (8)
O2—H2	0.8200	C1—C2	1.530 (2)
N1—C1	1.485 (5)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	108.0
C1—N1—H1A	109.5	C2—C1—H1	108.0
C1—N1—H1B	109.5	O1—C2—O3	125.94 (15)
H1A—N1—H1B	109.5	O1—C2—C1	117.7 (3)
C1—N1—H1C	109.5	O3—C2—C1	116.4 (3)
H1A—N1—H1C	109.5	O2—C3—C1	112.6 (2)
H1B—N1—H1C	109.5	O2—C3—H3A	109.1
C3—C1—N1	112.81 (19)	C1—C3—H3A	109.1
C3—C1—C2	111.4 (4)	O2—C3—H3B	109.1
N1—C1—C2	108.5 (3)	C1—C3—H3B	109.1
C3—C1—H1	108.0	H3A—C3—H3B	107.8
C3—C1—C2—O1	128.7 (3)	N1—C1—C2—O3	−176.5 (3)
N1—C1—C2—O1	3.9 (4)	N1—C1—C3—O2	73.6 (3)
C3—C1—C2—O3	−51.8 (3)	C2—C1—C3—O2	−48.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.91	2.702 (4)	147
N1—H1A···O3^ii	0.89	1.95	2.8145 (15)	164
N1—H1C···O3^iii	0.89	1.94	2.7915 (15)	159
O2—H2···O1^ii	0.82	1.80	2.616 (2)	174

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine3.7GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.763 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.7576 (6) Å	Cell parameters from 1547 reflections
b = 8.7046 (6) Å	θ = 2.3–30.9°
c = 9.785 (11) Å	µ = 0.16 mm^−1
β = 102.25 (4)°	T = 293 K
V = 396.0 (5) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	358 independent reflections
Radiation source: Enhance (Mo) X-ray Source	307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.0°, θmin = 4.5°
rotation method scans	h = −6→6
Absorption correction: GAUSSIAN Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −12→12
Tmin = 0.396, Tmax = 0.474	l = −4→4
3026 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0479P)^2] where P = (Fo^2 + 2Fc^2)/3
358 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.11 e Å^−3
55 restraints	Δρmin = −0.12 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2601 (3)	0.37727 (10)	0.3336 (4)	0.027 (2)
O2	0.3340 (3)	0.13902 (12)	0.0543 (4)	0.024 (2)
H2	0.2997	0.0578	0.0900	0.029*
N1	0.6168 (3)	0.14714 (13)	0.3626 (5)	0.018 (2)
H1A	0.4445	0.1027	0.3425	0.021*
H1B	0.6388	0.1962	0.4440	0.021*
H1C	0.7527	0.0757	0.3682	0.021*
O3	0.3913 (3)	0.48023 (12)	0.1496 (4)	0.026 (2)
C1	0.6411 (4)	0.25858 (18)	0.2507 (6)	0.021 (2)
H1	0.8295	0.3086	0.2766	0.025*
C2	0.4097 (4)	0.38214 (15)	0.2436 (6)	0.020 (3)
C3	0.6198 (4)	0.18582 (19)	0.1136 (7)	0.025 (2)
H3A	0.6840	0.2577	0.0509	0.030*
H3B	0.7456	0.0970	0.1237	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0218 (7)	0.0222 (5)	0.042 (7)	0.0008 (4)	0.0172 (18)	−0.0030 (10)
O2	0.0315 (7)	0.0170 (5)	0.021 (7)	−0.0030 (4)	−0.0030 (15)	0.0029 (10)
N1	0.0168 (8)	0.0185 (6)	0.017 (8)	0.0011 (5)	0.0030 (19)	−0.0032 (12)
O3	0.0242 (7)	0.0197 (5)	0.035 (7)	0.0023 (4)	0.0108 (17)	0.0059 (11)
C1	0.0149 (8)	0.0169 (7)	0.032 (6)	0.0000 (5)	0.0060 (19)	−0.0025 (15)
C2	0.0133 (8)	0.0138 (6)	0.033 (8)	−0.0035 (5)	0.003 (2)	−0.0041 (14)
C3	0.0227 (10)	0.0216 (8)	0.029 (8)	0.0039 (6)	0.005 (2)	−0.003 (2)

Geometric parameters (Å, º)

O1—C2	1.245 (5)	O3—C2	1.244 (5)
O2—C3	1.420 (4)	C1—C3	1.468 (8)
O2—H2	0.8200	C1—C2	1.530 (2)
N1—C1	1.485 (5)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	N1—C1—H1	108.0
C1—N1—H1A	109.5	C2—C1—H1	108.0
C1—N1—H1B	109.5	O3—C2—O1	125.80 (16)
H1A—N1—H1B	109.5	O3—C2—C1	117.0 (3)
C1—N1—H1C	109.5	O1—C2—C1	117.2 (3)
H1A—N1—H1C	109.5	O2—C3—C1	111.8 (3)
H1B—N1—H1C	109.5	O2—C3—H3A	109.3
C3—C1—N1	113.0 (2)	C1—C3—H3A	109.3
C3—C1—C2	110.6 (4)	O2—C3—H3B	109.3
N1—C1—C2	109.0 (3)	C1—C3—H3B	109.3
C3—C1—H1	108.0	H3A—C3—H3B	107.9
C3—C1—C2—O3	−51.5 (3)	N1—C1—C2—O1	4.9 (4)
N1—C1—C2—O3	−176.3 (3)	N1—C1—C3—O2	73.1 (3)
C3—C1—C2—O1	129.7 (3)	C2—C1—C3—O2	−49.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.91	2.689 (4)	145
N1—H1A···O3^ii	0.89	1.94	2.8013 (16)	164
N1—H1C···O3^iii	0.89	1.93	2.7784 (16)	159
O2—H2···O1^ii	0.82	1.79	2.608 (3)	177

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(DL-serine4.4GPa) 2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.785 Mg m^−3
Monoclinic, P21/n	Melting point: 501 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.7505 (6) Å	Cell parameters from 1837 reflections
b = 8.6644 (6) Å	θ = 2.4–31.0°
c = 9.725 (11) Å	µ = 0.16 mm^−1
β = 102.35 (4)°	T = 293 K
V = 391.0 (4) Å^3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	354 independent reflections
Radiation source: Enhance (Mo) X-ray Source	301 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
rotation method scans	θmax = 31.0°, θmin = 4.5°
Absorption correction: GAUSSIAN Absorb Angel (2004) J. Appl. Cryst. 37:486-492	h = −6→6
Tmin = 0.397, Tmax = 0.474	k = −12→12
3625 measured reflections	l = −4→4

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0444P)^2 + 0.0577P] where P = (Fo^2 + 2Fc^2)/3
354 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.11 e Å^−3
55 restraints	Δρmin = −0.11 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2615 (3)	0.37693 (11)	0.3358 (4)	0.025 (2)
O2	0.3373 (3)	0.13841 (13)	0.0528 (4)	0.029 (2)
H2	0.3037	0.0561	0.0877	0.035*
N1	0.6187 (3)	0.14613 (15)	0.3627 (5)	0.019 (3)
H1A	0.4472	0.1003	0.3407	0.023*
H1B	0.6368	0.1944	0.4450	0.023*
H1C	0.7568	0.0755	0.3690	0.023*
O3	0.3884 (3)	0.47987 (13)	0.1479 (4)	0.022 (2)
C1	0.6436 (4)	0.25867 (18)	0.2531 (6)	0.020 (2)
H1	0.8320	0.3091	0.2802	0.025*
C2	0.4109 (4)	0.38182 (16)	0.2452 (6)	0.023 (3)
C3	0.6241 (4)	0.1861 (2)	0.1137 (7)	0.025 (2)
H3A	0.6884	0.2591	0.0513	0.030*
H3B	0.7510	0.0972	0.1237	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0214 (7)	0.0221 (6)	0.036 (7)	0.0011 (4)	0.0144 (18)	−0.0011 (11)
O2	0.0306 (8)	0.0177 (6)	0.035 (7)	−0.0026 (4)	−0.0011 (17)	0.0038 (11)
N1	0.0182 (8)	0.0180 (6)	0.022 (8)	0.0014 (5)	0.005 (2)	−0.0016 (13)
O3	0.0224 (7)	0.0197 (6)	0.025 (7)	0.0012 (4)	0.0054 (19)	0.0038 (11)
C1	0.0153 (8)	0.0155 (7)	0.033 (7)	−0.0005 (6)	0.009 (2)	−0.0018 (16)
C2	0.0153 (8)	0.0128 (7)	0.043 (9)	−0.0031 (5)	0.010 (2)	−0.0034 (15)
C3	0.0209 (10)	0.0225 (8)	0.032 (8)	0.0031 (6)	0.006 (2)	−0.005 (2)

Geometric parameters (Å, º)

O1—C2	1.245 (5)	O3—C2	1.259 (5)
O2—C3	1.426 (4)	C1—C3	1.478 (8)
O2—H2	0.8200	C1—C2	1.527 (2)
N1—C1	1.468 (5)	C1—H1	0.9800
N1—H1A	0.8900	C3—H3A	0.9700
N1—H1B	0.8900	C3—H3B	0.9700
N1—H1C	0.8900
C3—O2—H2	109.5	C3—C1—H1	108.1
C1—N1—H1A	109.5	C2—C1—H1	108.1
C1—N1—H1B	109.5	O1—C2—O3	125.85 (17)
H1A—N1—H1B	109.5	O1—C2—C1	117.2 (3)
C1—N1—H1C	109.5	O3—C2—C1	116.9 (3)
H1A—N1—H1C	109.5	O2—C3—C1	111.8 (3)
H1B—N1—H1C	109.5	O2—C3—H3A	109.3
N1—C1—C3	112.6 (2)	C1—C3—H3A	109.3
N1—C1—C2	109.3 (3)	O2—C3—H3B	109.3
C3—C1—C2	110.4 (4)	C1—C3—H3B	109.3
N1—C1—H1	108.1	H3A—C3—H3B	107.9
N1—C1—C2—O1	6.1 (5)	C3—C1—C2—O3	−49.9 (3)
C3—C1—C2—O1	130.5 (3)	N1—C1—C3—O2	72.9 (3)
N1—C1—C2—O3	−174.2 (3)	C2—C1—C3—O2	−49.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.89	1.92	2.676 (5)	142
N1—H1A···O3^ii	0.89	1.93	2.7898 (17)	162
N1—H1C···O3^iii	0.89	1.92	2.7698 (17)	160
O2—H2···O1^ii	0.82	1.78	2.597 (3)	179

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

(L-serine0.1GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.578 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 742 reflections
a = 5.590 (2) Å	θ = 2.2–32.1°
b = 8.569 (13) Å	µ = 0.14 mm^−1
c = 9.233 (7) Å	T = 293 K
V = 442.2 (8) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	661 independent reflections
Radiation source: fine-focus sealed tube	334 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 10.3457 pixels mm^-1	θmax = 32.1°, θmin = 3.2°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −8→7
Tmin = 0.388, Tmax = 0.474	l = −12→12
2565 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0404P)^2] where P = (Fo^2 + 2Fc^2)/3
661 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2205 (5)	0.2032 (7)	0.8170 (4)	0.0466 (18)
H1	0.2428	0.2926	0.7699	0.056*
H2	0.2514	0.2171	0.9107	0.056*
H3	0.0696	0.1723	0.8061	0.056*
O1	0.7981 (6)	0.0256 (6)	0.7571 (4)	0.0605 (19)
O2	0.6768 (5)	0.2247 (7)	0.8857 (4)	0.053 (2)
C1	0.3853 (6)	0.0813 (8)	0.7570 (4)	0.0357 (19)
H4	0.3360	−0.0208	0.7943	0.043*
O3	0.4242 (6)	0.2312 (6)	0.5348 (4)	0.0543 (19)
H5	0.3015	0.2771	0.5112	0.065*
C2	0.3634 (9)	0.0794 (9)	0.5938 (5)	0.044 (2)
H6	0.4698	0.0010	0.5540	0.052*
H7	0.2009	0.0525	0.5667	0.052*
C3	0.6400 (9)	0.1130 (10)	0.8059 (5)	0.0370 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0304 (16)	0.080 (7)	0.029 (3)	−0.006 (3)	0.0003 (18)	0.002 (2)
O1	0.0369 (15)	0.056 (6)	0.088 (4)	0.006 (2)	0.004 (2)	−0.021 (2)
O2	0.0472 (18)	0.057 (7)	0.055 (3)	0.001 (3)	−0.012 (2)	−0.022 (2)
C1	0.0321 (19)	0.045 (7)	0.030 (3)	−0.005 (3)	0.008 (2)	0.004 (2)
O3	0.062 (2)	0.051 (6)	0.049 (3)	0.006 (3)	−0.002 (2)	0.013 (2)
C2	0.048 (3)	0.043 (9)	0.040 (4)	0.002 (4)	−0.006 (3)	−0.016 (3)
C3	0.042 (3)	0.030 (8)	0.038 (4)	−0.003 (4)	−0.001 (2)	0.005 (3)

Geometric parameters (Å, º)

N1—C1	1.499 (6)	C1—C3	1.518 (6)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.451 (8)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.242 (7)	C2—H6	0.9700
O2—C3	1.226 (8)	C2—H7	0.9700
C1—C2	1.511 (6)
C1—N1—H1	109.5	C3—C1—H4	108.6
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	110.2 (5)
C1—N1—H3	109.5	O3—C2—H6	109.6
H1—N1—H3	109.5	C1—C2—H6	109.6
H2—N1—H3	109.5	O3—C2—H7	109.6
N1—C1—C2	109.0 (4)	C1—C2—H7	109.6
N1—C1—C3	110.0 (4)	H6—C2—H7	108.1
C2—C1—C3	112.0 (4)	O2—C3—O1	124.7 (5)
N1—C1—H4	108.6	O2—C3—C1	118.4 (5)
C2—C1—H4	108.6	O1—C3—C1	116.8 (5)
N1—C1—C2—O3	59.1 (5)	C2—C1—C3—O2	122.9 (7)
C3—C1—C2—O3	−62.8 (6)	N1—C1—C3—O1	−176.0 (6)
N1—C1—C3—O2	1.5 (9)	C2—C1—C3—O1	−54.6 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	2.02	2.863 (5)	157
N1—H3···O2^i	0.89	2.36	3.110 (4)	142
N1—H2···O2^ii	0.89	1.99	2.824 (6)	156
N1—H1···O1^iii	0.89	2.02	2.848 (8)	153
O3—H5···O3^iv	0.82	2.15	2.886 (2)	149

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine0.3GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.573 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 737 reflections
a = 5.603 (3) Å	θ = 2.2–31.8°
b = 8.577 (15) Å	µ = 0.14 mm^−1
c = 9.231 (8) Å	T = 293 K
V = 443.7 (9) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	657 independent reflections
Radiation source: fine-focus sealed tube	338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.6°, θmin = 3.2°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −8→8
Tmin = 0.387, Tmax = 0.474	l = −12→12
2553 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0407P)^2] where P = (Fo^2 + 2Fc^2)/3
657 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2202 (5)	0.2014 (7)	0.8168 (4)	0.046 (2)
H1	0.2389	0.2908	0.7693	0.055*
H2	0.2520	0.2160	0.9103	0.055*
H3	0.0704	0.1685	0.8069	0.055*
O1	0.7985 (6)	0.0240 (6)	0.7570 (4)	0.0592 (19)
O2	0.6767 (5)	0.2244 (7)	0.8860 (4)	0.0508 (19)
C1	0.3858 (7)	0.0826 (8)	0.7568 (4)	0.0336 (19)
H4	0.3374	−0.0194	0.7944	0.040*
O3	0.4242 (7)	0.2301 (6)	0.5346 (4)	0.0556 (19)
H5	0.3039	0.2708	0.5009	0.067*
C2	0.3640 (9)	0.0780 (9)	0.5937 (5)	0.046 (2)
H6	0.4711	−0.0003	0.5547	0.055*
H7	0.2022	0.0504	0.5666	0.055*
C3	0.6419 (9)	0.1125 (10)	0.8050 (6)	0.040 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0324 (18)	0.075 (7)	0.030 (3)	−0.004 (3)	0.0004 (18)	−0.002 (2)
O1	0.0371 (16)	0.053 (7)	0.087 (4)	0.006 (2)	0.0067 (19)	−0.023 (3)
O2	0.0442 (18)	0.054 (7)	0.054 (3)	0.002 (3)	−0.0114 (19)	−0.019 (2)
C1	0.034 (2)	0.039 (7)	0.027 (3)	0.001 (3)	0.004 (2)	0.001 (2)
O3	0.066 (2)	0.054 (7)	0.047 (3)	0.006 (4)	−0.003 (2)	0.013 (2)
C2	0.043 (3)	0.058 (10)	0.037 (4)	0.001 (4)	−0.009 (3)	−0.012 (3)
C3	0.044 (3)	0.045 (9)	0.030 (4)	−0.007 (4)	0.003 (3)	0.001 (3)

Geometric parameters (Å, º)

N1—C1	1.485 (6)	C1—C3	1.524 (7)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.454 (8)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.242 (7)	C2—H6	0.9700
O2—C3	1.232 (8)	C2—H7	0.9700
C1—C2	1.511 (6)
C1—N1—H1	109.5	C3—C1—H4	107.9
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	109.4 (5)
C1—N1—H3	109.5	O3—C2—H6	109.8
H1—N1—H3	109.5	C1—C2—H6	109.8
H2—N1—H3	109.5	O3—C2—H7	109.8
N1—C1—C2	109.9 (4)	C1—C2—H7	109.8
N1—C1—C3	111.3 (4)	H6—C2—H7	108.2
C2—C1—C3	111.8 (4)	O2—C3—O1	125.5 (5)
N1—C1—H4	107.9	O2—C3—C1	117.2 (5)
C2—C1—H4	107.9	O1—C3—C1	117.3 (5)
N1—C1—C2—O3	60.0 (5)	C2—C1—C3—O2	124.6 (8)
C3—C1—C2—O3	−64.1 (6)	N1—C1—C3—O1	−177.3 (6)
N1—C1—C3—O2	1.3 (9)	C2—C1—C3—O1	−54.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	2.02	2.864 (5)	159
N1—H3···O2^i	0.89	2.37	3.118 (5)	141
N1—H2···O2^ii	0.89	1.99	2.826 (6)	155
N1—H1···O1^iii	0.89	2.03	2.852 (8)	154
O3—H5···O3^iv	0.82	2.15	2.894 (2)	150

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine0.5GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.599 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 742 reflections
a = 5.5885 (14) Å	θ = 2.2–31.9°
b = 8.542 (9) Å	µ = 0.14 mm^−1
c = 9.146 (4) Å	T = 293 K
V = 436.6 (5) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	649 independent reflections
Radiation source: fine-focus sealed tube	306 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
Detector resolution: 10.3457 pixels mm^-1	θmax = 32.0°, θmin = 3.3°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −7→7
Tmin = 0.389, Tmax = 0.474	l = −12→12
2478 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0528P)^2] where P = (Fo^2 + 2Fc^2)/3
649 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2192 (6)	0.1994 (7)	0.8173 (5)	0.040 (2)
H1	0.2421	0.2906	0.7723	0.048*
H2	0.2475	0.2105	0.9125	0.048*
H3	0.0687	0.1684	0.8039	0.048*
O1	0.7986 (6)	0.0224 (7)	0.7572 (5)	0.061 (2)
O2	0.6777 (6)	0.2251 (8)	0.8856 (5)	0.057 (2)
C1	0.3854 (8)	0.0802 (9)	0.7555 (5)	0.036 (2)
H4	0.3372	−0.0226	0.7929	0.044*
O3	0.4246 (7)	0.2275 (7)	0.5325 (5)	0.057 (2)
H5	0.3022	0.2724	0.5064	0.068*
C2	0.3644 (9)	0.0767 (10)	0.5913 (6)	0.043 (3)
H6	0.4714	−0.0021	0.5518	0.051*
H7	0.2021	0.0493	0.5637	0.051*
C3	0.6424 (9)	0.1109 (11)	0.8047 (7)	0.038 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0309 (17)	0.041 (8)	0.047 (4)	−0.007 (3)	0.000 (2)	0.001 (2)
O1	0.0369 (18)	0.065 (8)	0.082 (4)	0.009 (2)	0.000 (2)	−0.025 (3)
O2	0.047 (2)	0.069 (8)	0.055 (4)	0.002 (3)	−0.010 (2)	−0.020 (3)
C1	0.040 (2)	0.039 (9)	0.031 (4)	−0.009 (4)	0.007 (2)	−0.001 (2)
O3	0.058 (2)	0.063 (8)	0.050 (3)	0.007 (4)	0.006 (2)	0.009 (3)
C2	0.038 (3)	0.043 (10)	0.047 (5)	−0.006 (4)	−0.007 (3)	−0.003 (3)
C3	0.038 (3)	0.032 (9)	0.043 (5)	−0.009 (4)	−0.004 (2)	0.007 (3)

Geometric parameters (Å, º)

N1—C1	1.490 (7)	C1—C3	1.528 (7)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.436 (8)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.234 (8)	C2—H6	0.9700
O2—C3	1.240 (9)	C2—H7	0.9700
C1—C2	1.506 (7)
C1—N1—H1	109.5	C3—C1—H4	108.0
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	109.7 (6)
C1—N1—H3	109.5	O3—C2—H6	109.7
H1—N1—H3	109.5	C1—C2—H6	109.7
H2—N1—H3	109.5	O3—C2—H7	109.7
N1—C1—C2	110.1 (5)	C1—C2—H7	109.7
N1—C1—C3	110.9 (5)	H6—C2—H7	108.2
C2—C1—C3	111.8 (4)	O1—C3—O2	125.4 (5)
N1—C1—H4	108.0	O1—C3—C1	117.1 (6)
C2—C1—H4	108.0	O2—C3—C1	117.4 (6)
N1—C1—C2—O3	60.1 (6)	C2—C1—C3—O1	−54.7 (9)
C3—C1—C2—O3	−63.6 (7)	N1—C1—C3—O2	0.0 (10)
N1—C1—C3—O1	−178.0 (7)	C2—C1—C3—O2	123.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	2.00	2.848 (6)	158
N1—H3···O2^i	0.89	2.36	3.098 (5)	140
N1—H2···O2^ii	0.89	1.97	2.803 (7)	156
N1—H1···O1^iii	0.89	2.01	2.843 (8)	155
O3—H5···O3^iv	0.82	2.14	2.882 (2)	151

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine0.8GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.634 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 713 reflections
a = 5.5741 (17) Å	θ = 2.2–31.7°
b = 8.436 (9) Å	µ = 0.15 mm^−1
c = 9.088 (5) Å	T = 293 K
V = 427.3 (5) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	638 independent reflections
Radiation source: fine-focus sealed tube	327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.7°, θmin = 3.3°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −7→8
Tmin = 0.388, Tmax = 0.474	l = −11→11
2495 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0615P)^2] where P = (Fo^2 + 2Fc^2)/3
638 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2186 (6)	0.1998 (7)	0.8166 (4)	0.0379 (18)
H1	0.2344	0.2904	0.7674	0.045*
H2	0.2535	0.2157	0.9110	0.045*
H3	0.0682	0.1653	0.8086	0.045*
O1	0.7997 (6)	0.0222 (7)	0.7566 (5)	0.0586 (19)
O2	0.6773 (6)	0.2246 (7)	0.8853 (5)	0.0490 (19)
C1	0.3846 (8)	0.0797 (9)	0.7544 (5)	0.039 (2)
H4	0.3355	−0.0242	0.7919	0.047*
O3	0.4252 (7)	0.2288 (7)	0.5304 (5)	0.0549 (19)
H5	0.3054	0.2693	0.4940	0.066*
C2	0.3647 (9)	0.0752 (8)	0.5891 (6)	0.039 (2)
H6	0.4728	−0.0043	0.5498	0.046*
H7	0.2023	0.0472	0.5608	0.046*
C3	0.6421 (9)	0.1090 (11)	0.8044 (6)	0.043 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0312 (18)	0.036 (7)	0.046 (4)	0.000 (3)	0.002 (2)	0.003 (2)
O1	0.0348 (17)	0.058 (7)	0.083 (4)	0.004 (2)	0.008 (2)	−0.027 (3)
O2	0.044 (2)	0.043 (7)	0.060 (4)	0.002 (3)	−0.012 (2)	−0.018 (2)
C1	0.037 (2)	0.047 (9)	0.034 (4)	−0.010 (4)	0.010 (3)	−0.001 (3)
O3	0.056 (2)	0.064 (7)	0.045 (3)	0.006 (3)	0.002 (2)	0.009 (2)
C2	0.037 (3)	0.040 (9)	0.038 (5)	0.003 (4)	−0.009 (2)	−0.007 (3)
C3	0.036 (3)	0.068 (9)	0.025 (4)	−0.006 (4)	−0.001 (3)	−0.001 (3)

Geometric parameters (Å, º)

N1—C1	1.484 (7)	C1—C3	1.526 (7)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.441 (8)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.223 (7)	C2—H6	0.9700
O2—C3	1.236 (9)	C2—H7	0.9700
C1—C2	1.506 (7)
C1—N1—H1	109.5	C3—C1—H4	107.7
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	109.2 (5)
C1—N1—H3	109.5	O3—C2—H6	109.8
H1—N1—H3	109.5	C1—C2—H6	109.8
H2—N1—H3	109.5	O3—C2—H7	109.8
N1—C1—C2	110.5 (5)	C1—C2—H7	109.8
N1—C1—C3	111.3 (5)	H6—C2—H7	108.3
C2—C1—C3	111.7 (4)	O1—C3—O2	124.7 (5)
N1—C1—H4	107.7	O1—C3—C1	118.2 (6)
C2—C1—H4	107.7	O2—C3—C1	117.0 (6)
N1—C1—C2—O3	60.0 (6)	C2—C1—C3—O1	−53.1 (9)
C3—C1—C2—O3	−64.5 (6)	N1—C1—C3—O2	−0.7 (10)
N1—C1—C3—O1	−177.2 (7)	C2—C1—C3—O2	123.4 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	1.98	2.827 (6)	159
N1—H3···O2^i	0.89	2.34	3.088 (5)	142
N1—H2···O2^ii	0.89	1.97	2.793 (6)	154
N1—H1···O1^iii	0.89	1.98	2.802 (8)	154
O3—H5···O3^iv	0.82	2.13	2.864 (2)	149

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine1.0GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.633 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 713 reflections
a = 5.5668 (17) Å	θ = 2.2–31.7°
b = 8.463 (10) Å	µ = 0.15 mm^−1
c = 9.072 (5) Å	T = 293 K
V = 427.4 (6) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	626 independent reflections
Radiation source: fine-focus sealed tube	343 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.7°, θmin = 3.3°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −8→7
Tmin = 0.395, Tmax = 0.474	l = −12→11
2426 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0539P)^2] where P = (Fo^2 + 2Fc^2)/3
626 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2190 (5)	0.1997 (7)	0.8154 (4)	0.0377 (17)
H1	0.2418	0.2913	0.7694	0.045*
H2	0.2477	0.2117	0.9113	0.045*
H3	0.0679	0.1683	0.8025	0.045*
O1	0.7995 (6)	0.0214 (6)	0.7568 (4)	0.0549 (18)
O2	0.6774 (5)	0.2239 (7)	0.8844 (4)	0.0461 (18)
C1	0.3849 (7)	0.0793 (8)	0.7540 (5)	0.033 (2)
H4	0.3363	−0.0243	0.7919	0.040*
O3	0.4255 (7)	0.2283 (6)	0.5288 (4)	0.0529 (19)
H5	0.3042	0.2692	0.4946	0.063*
C2	0.3665 (8)	0.0753 (8)	0.5881 (5)	0.039 (2)
H6	0.4760	−0.0034	0.5490	0.047*
H7	0.2046	0.0464	0.5593	0.047*
C3	0.6430 (8)	0.1109 (11)	0.8042 (6)	0.041 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0288 (16)	0.047 (6)	0.038 (3)	−0.004 (3)	−0.0011 (18)	0.002 (2)
O1	0.0313 (15)	0.047 (6)	0.087 (4)	0.010 (2)	0.0047 (19)	−0.025 (3)
O2	0.0430 (18)	0.048 (7)	0.047 (3)	0.000 (3)	−0.0153 (18)	−0.017 (2)
C1	0.0298 (18)	0.037 (8)	0.033 (4)	−0.004 (3)	0.000 (2)	−0.002 (2)
O3	0.059 (2)	0.051 (7)	0.048 (3)	0.013 (3)	0.001 (2)	0.011 (2)
C2	0.038 (2)	0.041 (9)	0.037 (5)	0.010 (3)	−0.011 (2)	−0.006 (3)
C3	0.036 (2)	0.052 (8)	0.035 (4)	−0.007 (4)	0.002 (2)	−0.002 (3)

Geometric parameters (Å, º)

N1—C1	1.484 (6)	C1—C3	1.530 (7)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.440 (7)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.232 (7)	C2—H6	0.9700
O2—C3	1.217 (8)	C2—H7	0.9700
C1—C2	1.509 (7)
C1—N1—H1	109.5	C3—C1—H4	108.1
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	109.7 (5)
C1—N1—H3	109.5	O3—C2—H6	109.7
H1—N1—H3	109.5	C1—C2—H6	109.7
H2—N1—H3	109.5	O3—C2—H7	109.7
N1—C1—C2	110.4 (4)	C1—C2—H7	109.7
N1—C1—C3	110.6 (4)	H6—C2—H7	108.2
C2—C1—C3	111.3 (4)	O2—C3—O1	125.5 (5)
N1—C1—H4	108.1	O2—C3—C1	117.6 (5)
C2—C1—H4	108.1	O1—C3—C1	116.9 (5)
N1—C1—C2—O3	59.2 (5)	C2—C1—C3—O2	123.5 (8)
C3—C1—C2—O3	−64.1 (6)	N1—C1—C3—O1	−177.9 (6)
N1—C1—C3—O2	0.4 (9)	C2—C1—C3—O1	−54.8 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	1.99	2.831 (5)	158
N1—H3···O2^i	0.89	2.34	3.086 (4)	141
N1—H2···O2^ii	0.89	1.97	2.808 (5)	156
N1—H1···O1^iii	0.89	1.98	2.803 (8)	154
O3—H5···O3^iv	0.82	2.12	2.8557 (18)	150

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine2.1GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.700 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 672 reflections
a = 5.514 (2) Å	θ = 2.3–31.9°
b = 8.396 (11) Å	µ = 0.15 mm^−1
c = 8.868 (6) Å	T = 293 K
V = 410.6 (6) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	582 independent reflections
Radiation source: fine-focus sealed tube	310 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
Detector resolution: 10.3457 pixels mm^-1	θmax = 32.0°, θmin = 3.3°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −7→7
Tmin = 0.386, Tmax = 0.474	l = −11→11
2298 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0371P)^2] where P = (Fo^2 + 2Fc^2)/3
582 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2171 (5)	0.1988 (6)	0.8144 (4)	0.0355 (16)
H1	0.2371	0.2899	0.7645	0.043*
H2	0.2498	0.2139	0.9116	0.043*
H3	0.0645	0.1659	0.8042	0.043*
O1	0.8012 (5)	0.0198 (6)	0.7542 (4)	0.0581 (17)
O2	0.6800 (5)	0.2238 (6)	0.8844 (4)	0.0492 (18)
C1	0.3836 (7)	0.0767 (8)	0.7523 (5)	0.037 (2)
H4	0.3334	−0.0276	0.7908	0.045*
O3	0.4278 (6)	0.2245 (6)	0.5207 (4)	0.0503 (17)
H5	0.3037	0.2697	0.4929	0.060*
C2	0.3670 (8)	0.0732 (7)	0.5833 (5)	0.039 (2)
H6	0.4767	−0.0071	0.5441	0.047*
H7	0.2034	0.0446	0.5536	0.047*
C3	0.6436 (8)	0.1072 (9)	0.8032 (6)	0.041 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0316 (15)	0.027 (6)	0.048 (3)	−0.003 (3)	0.003 (2)	0.007 (2)
O1	0.0284 (14)	0.040 (6)	0.106 (4)	0.004 (2)	0.001 (2)	−0.029 (3)
O2	0.0426 (17)	0.058 (6)	0.047 (3)	0.002 (3)	−0.0135 (19)	−0.019 (2)
C1	0.038 (2)	0.042 (8)	0.032 (4)	−0.001 (3)	0.011 (2)	0.001 (2)
O3	0.0526 (17)	0.050 (6)	0.049 (3)	0.008 (3)	0.002 (2)	0.019 (2)
C2	0.037 (2)	0.060 (8)	0.020 (4)	0.000 (3)	−0.006 (2)	−0.005 (3)
C3	0.027 (2)	0.073 (8)	0.022 (4)	−0.012 (3)	−0.009 (2)	0.000 (3)

Geometric parameters (Å, º)

N1—C1	1.482 (6)	C1—C3	1.524 (6)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.426 (7)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.218 (6)	C2—H6	0.9700
O2—C3	1.232 (7)	C2—H7	0.9700
C1—C2	1.501 (6)
C1—N1—H1	109.5	C3—C1—H4	108.3
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	111.0 (5)
C1—N1—H3	109.5	O3—C2—H6	109.4
H1—N1—H3	109.5	C1—C2—H6	109.4
H2—N1—H3	109.5	O3—C2—H7	109.4
N1—C1—C2	110.2 (4)	C1—C2—H7	109.4
N1—C1—C3	110.8 (4)	H6—C2—H7	108.0
C2—C1—C3	110.9 (4)	O1—C3—O2	124.8 (4)
N1—C1—H4	108.3	O1—C3—C1	117.6 (5)
C2—C1—H4	108.3	O2—C3—C1	117.4 (5)
N1—C1—C2—O3	59.1 (5)	C2—C1—C3—O1	−53.8 (8)
C3—C1—C2—O3	−64.0 (6)	N1—C1—C3—O2	−0.3 (9)
N1—C1—C3—O1	−176.5 (6)	C2—C1—C3—O2	122.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	1.95	2.793 (5)	157
N1—H3···O2^i	0.89	2.29	3.033 (4)	141
N1—H2···O2^ii	0.89	1.92	2.757 (5)	156
N1—H1···O1^iii	0.89	1.95	2.765 (7)	152
O3—H5···O3^iv	0.82	2.08	2.8141 (18)	149

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine3.1GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.713 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 657 reflections
a = 5.5267 (18) Å	θ = 2.3–31.8°
b = 8.366 (10) Å	µ = 0.15 mm^−1
c = 8.812 (5) Å	T = 293 K
V = 407.5 (6) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	588 independent reflections
Radiation source: fine-focus sealed tube	298 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.9°, θmin = 3.4°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −7→7
Tmin = 0.393, Tmax = 0.474	l = −11→11
2257 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0399P)^2] where P = (Fo^2 + 2Fc^2)/3
588 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2175 (5)	0.1955 (8)	0.8129 (4)	0.0364 (18)
H1	0.2400	0.2881	0.7653	0.044*
H2	0.2469	0.2078	0.9115	0.044*
H3	0.0653	0.1635	0.7999	0.044*
O1	0.8036 (6)	0.0169 (7)	0.7526 (5)	0.0571 (19)
O2	0.6807 (6)	0.2253 (8)	0.8844 (5)	0.051 (2)
C1	0.3839 (7)	0.0742 (8)	0.7497 (5)	0.030 (2)
H4	0.3345	−0.0308	0.7881	0.037*
O3	0.4287 (6)	0.2218 (7)	0.5141 (5)	0.046 (2)
H5	0.3059	0.2664	0.4835	0.055*
C2	0.3660 (9)	0.0715 (8)	0.5795 (6)	0.039 (2)
H6	0.4731	−0.0103	0.5399	0.047*
H7	0.2020	0.0441	0.5503	0.047*
C3	0.6460 (9)	0.1062 (10)	0.8027 (6)	0.030 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0319 (17)	0.033 (7)	0.044 (4)	−0.004 (3)	0.007 (2)	0.003 (2)
O1	0.0301 (15)	0.032 (7)	0.109 (4)	0.004 (2)	0.001 (2)	−0.021 (3)
O2	0.0430 (19)	0.059 (7)	0.051 (3)	−0.008 (3)	−0.010 (2)	−0.021 (2)
C1	0.031 (2)	0.038 (9)	0.023 (4)	−0.001 (3)	0.004 (2)	0.001 (2)
O3	0.048 (2)	0.031 (7)	0.057 (4)	0.008 (3)	−0.003 (2)	0.018 (2)
C2	0.044 (3)	0.050 (10)	0.023 (4)	−0.001 (4)	0.003 (2)	−0.012 (3)
C3	0.029 (2)	0.036 (8)	0.026 (4)	−0.005 (4)	−0.003 (2)	0.005 (3)

Geometric parameters (Å, º)

N1—C1	1.478 (7)	C1—C3	1.545 (7)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.425 (8)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.229 (6)	C2—H6	0.9700
O2—C3	1.244 (8)	C2—H7	0.9700
C1—C2	1.504 (7)
C1—N1—H1	109.5	C3—C1—H4	108.2
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	112.0 (6)
C1—N1—H3	109.5	O3—C2—H6	109.2
H1—N1—H3	109.5	C1—C2—H6	109.2
H2—N1—H3	109.5	O3—C2—H7	109.2
N1—C1—C2	110.2 (4)	C1—C2—H7	109.2
N1—C1—C3	110.5 (4)	H6—C2—H7	107.9
C2—C1—C3	111.4 (4)	O1—C3—O2	125.8 (5)
N1—C1—H4	108.2	O1—C3—C1	116.8 (5)
C2—C1—H4	108.2	O2—C3—C1	117.3 (5)
N1—C1—C2—O3	60.3 (6)	C2—C1—C3—O1	−54.3 (8)
C3—C1—C2—O3	−62.7 (6)	N1—C1—C3—O2	−1.4 (9)
N1—C1—C3—O1	−177.1 (6)	C2—C1—C3—O2	121.5 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	1.94	2.783 (6)	157
N1—H3···O2^i	0.89	2.31	3.043 (5)	140
N1—H2···O2^ii	0.89	1.92	2.756 (5)	156
N1—H1···O1^iii	0.89	1.94	2.753 (8)	152
O3—H5···O3^iv	0.82	2.09	2.814 (2)	148

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine4.0GPa) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.767 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 557 reflections
a = 5.489 (2) Å	θ = 2.4–31.8°
b = 8.339 (10) Å	µ = 0.16 mm^−1
c = 8.632 (6) Å	T = 293 K
V = 395.1 (6) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	549 independent reflections
Radiation source: fine-focus sealed tube	254 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.130
Detector resolution: 10.3457 pixels mm^-1	θmax = 31.9°, θmin = 3.4°
rotation method scans	h = −8→8
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −8→8
Tmin = 0.394, Tmax = 0.473	l = −10→11
2131 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0471P)^2] where P = (Fo^2 + 2Fc^2)/3
549 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2162 (6)	0.1990 (8)	0.8133 (5)	0.0374 (18)
H1	0.2464	0.2933	0.7690	0.045*
H2	0.2386	0.2070	0.9152	0.045*
H3	0.0629	0.1704	0.7943	0.045*
O1	0.8042 (8)	0.0127 (8)	0.7505 (5)	0.058 (2)
O2	0.6808 (7)	0.2266 (8)	0.8816 (6)	0.050 (2)
C1	0.3862 (9)	0.0747 (8)	0.7486 (6)	0.0276 (19)
H4	0.3354	−0.0303	0.7881	0.033*
O3	0.4245 (8)	0.2230 (8)	0.5106 (5)	0.055 (2)
H5	0.2987	0.2689	0.4849	0.066*
C2	0.3662 (10)	0.0716 (9)	0.5767 (7)	0.041 (2)
H6	0.4758	−0.0092	0.5357	0.049*
H7	0.2014	0.0422	0.5477	0.049*
C3	0.6477 (12)	0.1048 (12)	0.8013 (7)	0.040 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.040 (2)	0.039 (7)	0.034 (4)	−0.005 (3)	0.007 (2)	0.003 (2)
O1	0.047 (2)	0.032 (7)	0.097 (5)	0.006 (3)	0.000 (3)	−0.020 (3)
O2	0.041 (2)	0.060 (8)	0.048 (4)	−0.002 (3)	−0.008 (2)	−0.012 (3)
C1	0.045 (3)	0.010 (8)	0.028 (5)	−0.007 (4)	0.001 (3)	0.003 (2)
O3	0.046 (2)	0.071 (8)	0.048 (4)	0.002 (3)	0.000 (2)	0.017 (3)
C2	0.052 (3)	0.048 (10)	0.023 (5)	−0.011 (4)	0.005 (3)	−0.001 (3)
C3	0.052 (4)	0.044 (9)	0.023 (5)	0.002 (5)	0.003 (3)	0.001 (3)

Geometric parameters (Å, º)

N1—C1	1.502 (7)	C1—C3	1.527 (8)
N1—H1	0.8900	C1—H4	0.9800
N1—H2	0.8900	O3—C2	1.422 (8)
N1—H3	0.8900	O3—H5	0.8200
O1—C3	1.233 (8)	C2—H6	0.9700
O2—C3	1.243 (9)	C2—H7	0.9700
C1—C2	1.488 (8)
C1—N1—H1	109.5	C3—C1—H4	108.1
C1—N1—H2	109.5	C2—O3—H5	109.5
H1—N1—H2	109.5	O3—C2—C1	111.6 (7)
C1—N1—H3	109.5	O3—C2—H6	109.3
H1—N1—H3	109.5	C1—C2—H6	109.3
H2—N1—H3	109.5	O3—C2—H7	109.3
C2—C1—N1	109.7 (5)	C1—C2—H7	109.3
C2—C1—C3	111.7 (4)	H6—C2—H7	108.0
N1—C1—C3	111.1 (5)	O1—C3—O2	127.3 (6)
C2—C1—H4	108.1	O1—C3—C1	116.5 (6)
N1—C1—H4	108.1	O2—C3—C1	116.0 (6)
N1—C1—C2—O3	59.3 (6)	N1—C1—C3—O1	−177.6 (8)
C3—C1—C2—O3	−64.4 (7)	C2—C1—C3—O2	120.1 (9)
C2—C1—C3—O1	−54.8 (10)	N1—C1—C3—O2	−2.7 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.89	1.97	2.797 (6)	154
N1—H3···O2^i	0.89	2.28	3.006 (5)	139
N1—H2···O2^ii	0.89	1.87	2.712 (7)	158
N1—H1···O1^iii	0.89	1.86	2.675 (9)	152
O3—H5···O3^iv	0.82	2.06	2.787 (2)	148

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

(L-serine5.0GPa-phase-II) (S)-2-amino-3-hydroxypropanoic acid

Crystal data

C3H7NO3	F(000) = 224
Mr = 105.10	Dx = 1.862 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 577 reflections
a = 5.631 (3) Å	θ = 2.1–31.8°
b = 6.921 (15) Å	µ = 0.17 mm^−1
c = 9.619 (8) Å	T = 293 K
V = 374.9 (9) Å^3	Prism, colourless
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	365 independent reflections
Radiation source: fine-focus sealed tube	241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.3°, θmin = 4.2°
rotation method scans	h = −7→7
Absorption correction: gaussian Absorb Angel (2004) J. Appl. Cryst. 37:486-492	k = −5→5
Tmin = 0.390, Tmax = 0.474	l = −11→11
1637 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0182P)^2] where P = (Fo^2 + 2Fc^2)/3
365 reflections	(Δ/σ)max < 0.001
61 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0412 (8)	0.1419 (16)	0.2136 (6)	0.0304 (13)*
C2	0.2148 (8)	0.0877 (15)	0.2539 (4)	0.025 (3)
H1	0.2448	−0.0477	0.2298	0.030*
C3	0.2699 (10)	0.1198 (12)	0.4039 (5)	0.029 (3)
H2	0.1479	0.0627	0.4620	0.035*
H3	0.4215	0.0619	0.4276	0.035*
N1	0.3748 (6)	0.2146 (12)	0.1718 (4)	0.040 (3)
H4	0.3444	0.1998	0.0816	0.048*
H5	0.5252	0.1828	0.1887	0.048*
H6	0.3507	0.3372	0.1958	0.048*
O1	−0.0743 (4)	0.2208 (8)	0.0996 (4)	0.043 (3)
O2	−0.2000 (5)	0.1056 (8)	0.3027 (3)	0.035 (2)
O3	0.2779 (8)	0.3221 (10)	0.4234 (3)	0.045 (2)
H7	0.3072	0.3460	0.5051	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.028 (2)	0.024 (9)	0.024 (3)	0.021 (4)	0.009 (2)	0.010 (3)
C3	0.028 (3)	0.013 (13)	0.046 (4)	0.000 (6)	0.000 (3)	−0.005 (3)
N1	0.0293 (16)	0.058 (10)	0.032 (3)	−0.001 (4)	−0.0051 (18)	−0.010 (3)
O1	0.0396 (18)	0.060 (9)	0.030 (3)	0.006 (3)	−0.0059 (18)	0.006 (2)
O2	0.0305 (19)	0.045 (8)	0.031 (2)	−0.002 (3)	0.0058 (17)	−0.0015 (19)
O3	0.061 (3)	0.044 (8)	0.030 (2)	−0.003 (5)	−0.003 (2)	−0.001 (3)

Geometric parameters (Å, º)

C1—O1	1.239 (7)	C3—H2	0.9700
C1—O2	1.264 (6)	C3—H3	0.9700
C1—C2	1.540 (7)	N1—H4	0.8900
C2—N1	1.485 (8)	N1—H5	0.8900
C2—C3	1.492 (7)	N1—H6	0.8900
C2—H1	0.9800	O3—H7	0.8200
C3—O3	1.414 (10)
O1—C1—O2	125.6 (4)	C2—C3—H2	110.4
O1—C1—C2	118.1 (5)	O3—C3—H3	110.4
O2—C1—C2	116.3 (5)	C2—C3—H3	110.4
N1—C2—C3	107.5 (6)	H2—C3—H3	108.6
N1—C2—C1	106.9 (5)	C2—N1—H4	109.5
C3—C2—C1	113.7 (5)	C2—N1—H5	109.5
N1—C2—H1	109.6	H4—N1—H5	109.5
C3—C2—H1	109.6	C2—N1—H6	109.5
C1—C2—H1	109.6	H4—N1—H6	109.5
O3—C3—C2	106.4 (6)	H5—N1—H6	109.5
O3—C3—H2	110.4	C3—O3—H7	109.5
O1—C1—C2—N1	23.1 (11)	O2—C1—C2—C3	−36.8 (13)
O2—C1—C2—N1	−155.2 (7)	N1—C2—C3—O3	47.4 (6)
O1—C1—C2—C3	141.5 (8)	C1—C2—C3—O3	−70.6 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O1^i	0.89	1.88	2.664 (6)	145
N1—H5···O1^ii	0.89	2.43	3.180 (4)	142
N1—H5···O2^ii	0.89	1.97	2.809 (5)	156
N1—H6···O2^iii	0.89	2.04	2.890 (11)	159
O3—H7···O2^iv	0.82	1.88	2.685 (5)	167

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.