Charge density study of N-acetyl-l-tyrosine ethyl ester monohydrate derived from CCD area detector data

Dahaoui, S.; Jelsch, C.; Howard, J.A.K.; Lecomte, C.

doi:10.1107/S0108768198012099

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Charge density study of N-acetyl-L-tyrosine ethyl ester monohydrate derived from CCD area detector data

S. Dahaoui, C. Jelsch, J. A. K. Howard and C. Lecomte

The crystal structure, thermal vibrations and electron density of the peptide N-acetyl-L-tyrosine ethyl ester monohydrate, C₁₃H₁₇NO₄.H₂O, have been analysed using single-crystal X-ray diffraction data collected at 110 K with Mo Kα radiation to a resolution of $(\sin\theta/\lambda)_\max = 1.1$ Å⁻¹. A CCD area detector was used to collect 98 393 data during one week. A multipolar atom density model was fitted against the 10 189 unique data with I > 2σ(I) [R(F)

0.027, wR(F)

0.020, g.o.f.

0.65] in order to map the valence electron distribution. These deformation densities compare very well with those obtained from conventional diffractometers equipped with scintillation detectors. This work shows that area detectors permit charge density studies in a more routine way than is possible with conventional diffractometers.

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Supporting information

	Crystallographic Information File (CIF) Contains datablocks 110, 293, global
	Structure factor file (CIF format) Contains datablock 110
	Structure factor file (CIF format) Contains datablock pepabs
	Portable Document Format (PDF) file Supplementary material

CCDC references: 132057; 132058

Computing details top

For both compounds, data collection: SMART system (Siemens, 1995); cell refinement: SMART system (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990). Program(s) used to refine structure: MOLLY (Hansen, 1978) for 110; SHELXL93 (Sheldrick, 1993) for 293. For both compounds, molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL93 (Sheldrick, 1993).

Figures top

(110) N-Acetyl-L-tyrosine Ethyl Ester Monohydrate top

Crystal data top

C₁₃H₁₇NO₄·H₂O	D_x = 1.313 Mg m⁻³
M_r = 269.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 512 reflections
a = 7.235 (2) Å	θ = 11–45°
b = 13.056 (4) Å	µ = 0.10 mm⁻¹
c = 14.415 (4) Å	T = 110 K
V = 1361.6 (12) Å³	Prism, colourless
Z = 4	0.3 × 0.2 × 0.2 mm
F(000) = 576

Data collection top

Siemens SMART-CCD diffractometer	10189 reflections with I > 2σ(I)
Radiation source: rotating anode tube	R_int = 0.027
Graphite monochromator	θ_max = 51.1°, θ_min = 2.1°
ω scan	h = −15→15
98393 measured reflections	k = −28→28
14787 independent reflections	l = −31→31

Refinement top

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.027	Calculated w = 1/[σ²(F_o²)]
wR(F²) = 0.0202	(Δ/σ)_max = −0.006
10189 reflections	Δρ_max = 0.14 e Å⁻³
544 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.63 (115)
Secondary atom site location: difference Fourier map

Crystal data top

C₁₃H₁₇NO₄·H₂O	V = 1361.6 (12) Å³
M_r = 269.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.235 (2) Å	µ = 0.10 mm⁻¹
b = 13.056 (4) Å	T = 110 K
c = 14.415 (4) Å	0.3 × 0.2 × 0.2 mm

Data collection top

Siemens SMART-CCD diffractometer	10189 reflections with I > 2σ(I)
98393 measured reflections	R_int = 0.027
14787 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	All H-atom parameters refined
wR(F²) = 0.0202	Δρ_max = 0.14 e Å⁻³
10189 reflections	Δρ_min = −0.17 e Å⁻³
544 parameters	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
0 restraints	Absolute structure parameter: 1.63 (115)

Special details top

Experimental. Crystal to Detector distance was 4.51 cm, ω range is 0.2 ° and exposure time was 20 s at low angles and 40 s at high angles.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.23164 (13)	0.20571 (4)	0.42334 (4)	0.0201 (1)
O	0.57804 (8)	0.03798 (4)	0.37422 (5)	0.0170 (1)
O2	0.19614 (9)	0.12871 (4)	0.56155 (4)	0.0149 (1)
OH	−0.02619 (10)	−0.44263 (4)	0.32345 (4)	0.0185 (1)
HH	0.031 (4)	−0.491 (2)	0.364 (2)	0.023 (2)*
N	0.27588 (7)	0.01970 (3)	0.33598 (3)	0.0123 (1)
H	0.178 (4)	0.024 (4)	0.284 (2)	0.0154 (19)*
CA	0.21351 (6)	0.01977 (3)	0.43117 (3)	0.0109 (1)
HA	0.311 (2)	−0.024 (2)	0.472 (2)	0.0137 (17)*
C	0.45551 (7)	0.03238 (3)	0.31432 (3)	0.0128 (1)
C2	0.21534 (6)	0.12880 (3)	0.47020 (3)	0.0118 (1)
CG	0.00760 (7)	−0.13705 (3)	0.40996 (3)	0.0124 (1)
CD1	0.10085 (7)	−0.21384 (4)	0.45900 (3)	0.0149 (1)
HD1	0.185 (4)	−0.193 (2)	0.517 (2)	0.019 (2)*
C3	0.20187 (9)	0.22828 (4)	0.60674 (4)	0.0178 (1)
H31	0.094 (4)	0.273 (2)	0.573 (2)	0.022 (2)*
H32	0.336 (4)	0.262 (2)	0.593 (2)	0.022 (2)*
CB	0.01763 (6)	−0.02579 (3)	0.43907 (3)	0.0134 (1)
HB1	−0.026 (5)	−0.016 (2)	0.510 (2)	0.0168 (16)*
HB2	−0.076 (4)	0.021 (2)	0.398 (2)	0.0168 (16)*
C1	0.49913 (8)	0.04026 (4)	0.21235 (3)	0.0205 (1)
H11	0.636 (5)	0.011 (3)	0.198 (2)	0.025 (3)*
H12	0.494 (5)	0.121 (3)	0.194 (2)	0.025 (3)*
H13	0.392 (5)	0.006 (3)	0.169 (2)	0.025 (3)*
CZ	−0.01333 (7)	−0.34367 (4)	0.35433 (3)	0.0136 (1)
CE2	−0.10879 (8)	−0.26824 (4)	0.30497 (4)	0.0178 (1)
HE2	−0.187 (4)	−0.288 (2)	0.244 (2)	0.022 (2)*
CE1	0.09113 (7)	−0.31631 (3)	0.43194 (3)	0.0148 (1)
HE1	0.161 (4)	−0.375 (2)	0.470 (2)	0.019 (2)*
CD2	−0.09781 (7)	−0.16620 (3)	0.33312 (3)	0.0165 (1)
HD2	−0.171 (2)	−0.107 (2)	0.295 (2)	0.021 (2)*
C4	0.16687 (10)	0.21257 (4)	0.70827 (4)	0.0260 (1)
H41	0.199 (4)	0.284 (2)	0.743 (2)	0.031 (2)*
H42	0.255 (4)	0.154 (2)	0.737 (2)	0.031 (2)*
H43	0.024 (4)	0.190 (2)	0.720 (2)	0.031 (2)*
OW	0.14436 (8)	0.42520 (4)	0.43837 (4)	0.0191 (1)
HW1	0.118 (4)	0.432 (2)	0.504 (2)	0.024 (2)*
HW2	0.158 (4)	0.353 (2)	0.426 (2)	0.024 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0355 (3)	0.01068 (15)	0.01406 (18)	0.00118 (18)	0.00384 (19)	0.00146 (14)
O	0.01324 (19)	0.0218 (2)	0.01590 (18)	−0.00126 (16)	−0.00122 (16)	−0.00271 (15)
O2	0.0239 (2)	0.00970 (14)	0.01103 (17)	0.00023 (16)	0.00065 (16)	−0.00136 (13)
OH	0.0253 (3)	0.01128 (16)	0.0184 (2)	0.00086 (16)	−0.00888 (19)	−0.00171 (14)
N	0.01215 (16)	0.01438 (15)	0.01019 (14)	0.00012 (13)	−0.00041 (13)	−0.00168 (11)
CA	0.01200 (14)	0.01000 (12)	0.01083 (13)	0.00071 (11)	−0.00016 (12)	−0.00123 (10)
C	0.01322 (17)	0.01359 (16)	0.01150 (15)	−0.00102 (12)	0.00057 (13)	−0.00267 (12)
C2	0.01517 (17)	0.00907 (13)	0.01110 (14)	0.00049 (12)	0.00059 (12)	−0.00043 (11)
CG	0.01322 (17)	0.01120 (14)	0.01278 (15)	−0.00057 (12)	−0.00120 (14)	−0.00101 (11)
CD1	0.01795 (19)	0.01264 (16)	0.01410 (15)	−0.0007 (14)	−0.00543 (15)	−0.00081 (12)
C3	0.0280 (3)	0.01063 (14)	0.01487 (17)	0.00054 (15)	0.00045 (17)	−0.00248 (13)
CB	0.01228 (15)	0.01213 (14)	0.01579 (15)	−0.00010 (12)	0.00099 (12)	−0.00257 (12)
C1	0.0227 (2)	0.0254 (2)	0.01337 (16)	−0.00591 (17)	0.00452 (15)	−0.00347 (14)
CZ	0.01665 (19)	0.01093 (15)	0.01327 (16)	−0.00017 (14)	−0.00403 (15)	−0.00068 (12)
CE2	0.0242 (2)	0.01213 (16)	0.01714 (18)	0.00123 (15)	−0.01004 (17)	−0.00136 (14)
CE1	0.01790 (17)	0.01205 (14)	0.01452 (16)	−0.00029 (16)	−0.00571 (15)	0.00006 (12)
CD2	0.02070 (19)	0.01174 (15)	0.01705 (17)	0.00096 (14)	−0.00726 (16)	−0.00062 (13)
C4	0.0487 (4)	0.01736 (18)	0.01260 (17)	0.0064 (2)	−0.00312 (19)	−0.00303 (14)
OW	0.0274 (2)	0.01407 (16)	0.01584 (19)	0.00282 (15)	−0.00161 (16)	0.00180 (13)

Geometric parameters (Å, º) top

O1—C2	1.2160 (6)	C—C1	1.5086 (6)
O—C	1.2390 (7)	CG—CD1	1.4001 (6)
O2—C2	1.3237 (7)	CG—CD2	1.3968 (6)
O2—C3	1.4545 (7)	CG—CB	1.5144 (5)
OH—CZ	1.3697 (6)	CD1—CE1	1.3960 (6)
N—C	1.3475 (7)	C3—C4	1.5008 (7)
N—CA	1.4444 (6)	CZ—CE1	1.3965 (6)
CA—C2	1.5307 (5)	CZ—CE2	1.3984 (6)
CA—CB	1.5422 (6)	CE2—CD2	1.3948 (6)

C2—O2—C3	116.23 (5)	CD1—CG—CB	121.60 (3)
C—N—CA	121.36 (4)	CD2—CG—CB	120.49 (3)
N—CA—C2	110.35 (3)	CG—CD1—CE1	121.40 (4)
N—CA—CB	110.85 (3)	O2—C3—C4	108.05 (4)
C2—CA—CB	109.77 (3)	CG—CB—CA	113.10 (3)
O—C—N	122.42 (5)	CE1—CZ—OH	122.57 (4)
O—C—C1	121.71 (5)	CE1—CZ—CE2	119.71 (4)
N—C—C1	115.87 (4)	OH—CZ—CE2	117.71 (4)
O1—C2—O2	124.27 (5)	CZ—CE2—CD2	119.70 (4)
O1—C2—CA	124.37 (4)	CZ—CE1—CD1	119.74 (3)
O2—C2—CA	111.36 (4)	CG—CD2—CE2	121.53 (4)
CD1—CG—CD2	117.91 (3)

O2—C2—CA—N	−167.3 (3)	CD1—CG—CB—CA	64.53 (5)
O1—C2—CA—N	13.34 (6)	CD2—CG—CB—CA	−116.17 (4)
CG—CB—CA—N	63.05 (4)	C—N—CA—C2	74.16 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HW2···O1	0.9647 (5)	2.0097 (5)	2.9420 (7)	161.93 (3)
OW—HW1···Oⁱ	0.9652 (6)	1.8280 (6)	2.7863 (8)	171.51 (3)
OH—HH···OWⁱⁱ	0.9675 (6)	1.7312 (4)	2.6912 (7)	171.10 (3)
N—H···OHⁱⁱⁱ	1.0321 (5)	1.9454 (5)	2.9640 (7)	168.51 (2)

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

(293) N-Acetyl-L-tyrosine Ethyl Ester Monohydrate top

Crystal data top

C₁₃H₁₇NO₄·H₂O	D_x = 1.270 Mg m⁻³
M_r = 269.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 411 reflections
a = 7.3827 (2) Å	θ = 11–45°
b = 13.1421 (4) Å	µ = 0.10 mm⁻¹
c = 14.5150 (4) Å	T = 293 K
V = 1408.31 (7) Å³	Prism, colourless
Z = 4	0.3 × 0.2 × 0.2 mm
F(000) = 576

Data collection top

Siemens SMART-CCD diffractometer	2660 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.1°
ω scans	h = −9→9
15638 measured reflections	k = −17→17
3241 independent reflections	l = −18→18

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.038	Calculated w = 1/[σ²(F_o²) + (0.0411P)² + 0.2434P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.100	(Δ/σ)_max = −0.006
S = 1.10	Δρ_max = 0.17 e Å⁻³
3238 reflections	Δρ_min = −0.16 e Å⁻³
249 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.044 (33)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 1.63 (115)

Crystal data top

C₁₃H₁₇NO₄·H₂O	V = 1408.31 (7) Å³
M_r = 269.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3827 (2) Å	µ = 0.10 mm⁻¹
b = 13.1421 (4) Å	T = 293 K
c = 14.5150 (4) Å	0.3 × 0.2 × 0.2 mm

Data collection top

Siemens SMART-CCD diffractometer	2660 reflections with I > 2σ(I)
15638 measured reflections	R_int = 0.032
3241 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	All H-atom parameters refined
wR(F²) = 0.100	Δρ_max = 0.17 e Å⁻³
S = 1.10	Δρ_min = −0.16 e Å⁻³
3238 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
249 parameters	Absolute structure parameter: 1.63 (115)
0 restraints

Special details top

Experimental. Crystal to Detector distance was 4.51 cm, ω range is 0.3 ° and exposure time was 10 s.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2154 (3)	0.20331 (10)	0.42472 (10)	0.0653 (5)
O	0.5662 (2)	0.03510 (13)	0.38004 (10)	0.0544 (4)
O2	0.1893 (2)	0.12768 (9)	0.56078 (9)	0.0544 (4)
OH	−0.0282 (2)	−0.44010 (11)	0.32293 (11)	0.0588 (4)
HH	0.022 (4)	−0.480 (2)	0.3613 (18)	0.067 (8)*
N	0.2735 (2)	0.01902 (12)	0.33857 (10)	0.0385 (3)
H	0.193 (3)	0.0227 (18)	0.2935 (16)	0.054 (6)*
CA	0.2063 (2)	0.01927 (13)	0.43251 (11)	0.0357 (4)
HA	0.287 (3)	−0.0193 (14)	0.4701 (12)	0.031 (4)*
C	0.4507 (3)	0.03053 (15)	0.31956 (13)	0.0432 (4)
C2	0.2049 (3)	0.12727 (13)	0.47049 (12)	0.0392 (4)
CG	0.0064 (3)	−0.13737 (13)	0.40918 (12)	0.0384 (4)
CD1	0.0981 (3)	−0.21311 (15)	0.45619 (14)	0.0477 (5)
HD1	0.176 (4)	−0.1962 (19)	0.5062 (17)	0.062 (7)*
C3	0.1894 (5)	0.2273 (2)	0.6058 (2)	0.0703 (8)
H31	0.100 (4)	0.268 (2)	0.5733 (19)	0.072 (8)*
H32	0.311 (4)	0.2426 (19)	0.6403 (18)	0.062 (7)*
CB	0.0156 (3)	−0.02671 (14)	0.43830 (14)	0.0432 (4)
HB1	−0.023 (3)	−0.0167 (17)	0.5058 (15)	0.053 (6)*
HB2	−0.072 (3)	0.0137 (17)	0.4001 (14)	0.049 (6)*
C1	0.4987 (4)	0.0390 (3)	0.2190 (2)	0.0659 (7)
H11	0.588 (6)	−0.004 (3)	0.207 (3)	0.118 (13)*
H12	0.503 (6)	0.108 (4)	0.206 (3)	0.138 (15)*
H13	0.397 (5)	0.016 (3)	0.177 (3)	0.113 (12)*
CZ	−0.0153 (3)	−0.34118 (13)	0.35436 (12)	0.0417 (4)
CE2	−0.1098 (3)	−0.2670 (2)	0.3069 (2)	0.0556 (6)
HE2	−0.175 (3)	−0.2823 (18)	0.2529 (17)	0.062 (7)*
CE1	0.0886 (3)	−0.31474 (15)	0.42960 (14)	0.0463 (5)
HE1	0.152 (3)	−0.3627 (19)	0.4637 (17)	0.058 (6)*
CD2	−0.0986 (3)	−0.1663 (2)	0.3347 (2)	0.0515 (5)
HD2	−0.160 (3)	−0.1110 (19)	0.3009 (15)	0.056 (6)*
C4	0.1647 (9)	0.2127 (3)	0.7049 (2)	0.127 (2)
H41	0.191 (5)	0.285 (3)	0.735 (3)	0.119 (12)*
H42	0.207 (6)	0.157 (3)	0.732 (3)	0.121 (13)*
H43	0.020 (18)	0.207 (8)	0.664 (7)	0.38 (6)*
OW	0.1445 (2)	0.42672 (13)	0.43466 (12)	0.0586 (4)
HW1	0.114 (5)	0.436 (3)	0.499 (3)	0.100 (11)*
HW2	0.151 (5)	0.369 (3)	0.427 (3)	0.105 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1149 (14)	0.0330 (7)	0.0479 (8)	0.0033 (8)	0.0047 (9)	0.0024 (6)
O	0.0426 (7)	0.0668 (9)	0.0538 (8)	−0.0027 (7)	−0.0049 (6)	−0.0095 (7)
O2	0.0910 (11)	0.0333 (7)	0.0388 (7)	0.0039 (7)	0.0023 (7)	−0.0058 (6)
OH	0.0830 (12)	0.0367 (7)	0.0565 (9)	0.0013 (7)	−0.0253 (8)	−0.0033 (6)
N	0.0396 (8)	0.0411 (8)	0.0348 (7)	0.0005 (7)	−0.0014 (6)	−0.0050 (6)
CA	0.0387 (9)	0.0331 (8)	0.0353 (8)	0.0029 (7)	−0.0021 (7)	−0.0037 (7)
C	0.0462 (11)	0.0386 (9)	0.0448 (10)	−0.0005 (8)	0.0014 (8)	−0.0106 (8)
C2	0.0453 (10)	0.0335 (9)	0.0388 (9)	0.0031 (8)	−0.0009 (8)	−0.0019 (7)
CG	0.0370 (9)	0.0364 (8)	0.0419 (9)	−0.0024 (7)	0.0029 (7)	−0.0015 (7)
CD1	0.0547 (12)	0.0438 (11)	0.0445 (10)	−0.0049 (9)	−0.0138 (9)	−0.0012 (8)
C3	0.120 (2)	0.0390 (11)	0.0517 (13)	0.0136 (14)	−0.0104 (15)	−0.0148 (9)
CB	0.0409 (10)	0.0385 (9)	0.0503 (10)	0.0018 (8)	0.0029 (9)	−0.0067 (9)
C1	0.067 (2)	0.084 (2)	0.0470 (12)	−0.013 (2)	0.0126 (12)	−0.0142 (12)
CZ	0.0477 (10)	0.0348 (9)	0.0425 (9)	−0.0023 (8)	−0.0070 (8)	−0.0017 (7)
CE2	0.0703 (14)	0.0426 (11)	0.0537 (12)	−0.0010 (10)	−0.0273 (11)	−0.0023 (9)
CE1	0.0514 (11)	0.0388 (9)	0.0486 (11)	0.0002 (8)	−0.0135 (9)	0.0037 (9)
CD2	0.0608 (13)	0.0376 (10)	0.0560 (12)	0.0039 (9)	−0.0190 (10)	0.0024 (9)
C4	0.261 (6)	0.061 (2)	0.058 (2)	0.038 (3)	−0.036 (3)	−0.0150 (14)
OW	0.0825 (12)	0.0421 (8)	0.0512 (9)	0.0050 (8)	−0.0045 (8)	0.0037 (7)

Geometric parameters (Å, º) top

O1—C2	1.203 (2)	C—C1	1.507 (3)
O—C	1.225 (2)	CG—CD1	1.384 (3)
O2—C2	1.316 (2)	CG—CD2	1.384 (3)
O2—C3	1.463 (2)	CG—CB	1.516 (2)
OH—CZ	1.381 (2)	CD1—CE1	1.392 (3)
N—C	1.345 (3)	C3—C4	1.462 (4)
N—CA	1.451 (2)	CZ—CE1	1.379 (3)
CA—C2	1.523 (2)	CZ—CE2	1.383 (3)
CA—CB	1.535 (3)	CE2—CD2	1.385 (3)

C2—O2—C3	116.7 (2)	CD1—CG—CB	122.1 (2)
C—N—CA	121.7 (2)	CD2—CG—CB	120.4 (2)
N—CA—C2	110.17 (14)	CG—CD1—CE1	121.9 (2)
N—CA—CB	111.37 (14)	O2—C3—C4	108.8 (2)
C2—CA—CB	109.91 (14)	CG—CB—CA	113.78 (15)
O—C—N	122.4 (2)	CE1—CZ—OH	122.5 (2)
O—C—C1	121.8 (2)	CE1—CZ—CE2	119.8 (2)
N—C—C1	115.8 (2)	OH—CZ—CE2	117.7 (2)
O1—C2—O2	123.5 (2)	CZ—CE2—CD2	119.9 (2)
O1—C2—CA	125.04 (15)	CZ—CE1—CD1	119.3 (2)
O2—C2—CA	111.42 (14)	CG—CD2—CE2	121.5 (2)
CD1—CG—CD2	117.5 (2)

Experimental details

	(110)	(293)
Crystal data
Chemical formula	C₁₃H₁₇NO₄·H₂O	C₁₃H₁₇NO₄·H₂O
M_r	269.29	269.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁
Temperature (K)	110	293
a, b, c (Å)	7.235 (2), 13.056 (4), 14.415 (4)	7.3827 (2), 13.1421 (4), 14.5150 (4)
V (Å³)	1361.6 (12)	1408.31 (7)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.10
Crystal size (mm)	0.3 × 0.2 × 0.2	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Siemens SMART-CCD diffractometer	Siemens SMART-CCD diffractometer
Absorption correction	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	98393, 14787, 10189	15638, 3241, 2660
R_int	0.027	0.032
(sin θ/λ)_max (Å⁻¹)	1.095	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.0202, ?	0.038, 0.100, 1.10
No. of reflections	10189	3238
No. of parameters	544	249
H-atom treatment	All H-atom parameters refined	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17	0.17, −0.16
Absolute structure	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter	1.63 (115)	1.63 (115)

Computer programs: SMART system (Siemens, 1995), SAINT (Siemens, 1995), SHELXS86 (Sheldrick, 1990), MOLLY (Hansen, 1978), SHELXL93 (Sheldrick, 1993), SHELXTL-Plus (Sheldrick, 1991).

Selected geometric parameters (Å, º) for (110) top

O1—C2	1.2160 (6)	C—C1	1.5086 (6)
O—C	1.2390 (7)	CG—CD1	1.4001 (6)
O2—C2	1.3237 (7)	CG—CD2	1.3968 (6)
O2—C3	1.4545 (7)	CG—CB	1.5144 (5)
OH—CZ	1.3697 (6)	CD1—CE1	1.3960 (6)
N—C	1.3475 (7)	C3—C4	1.5008 (7)
N—CA	1.4444 (6)	CZ—CE1	1.3965 (6)
CA—C2	1.5307 (5)	CZ—CE2	1.3984 (6)
CA—CB	1.5422 (6)	CE2—CD2	1.3948 (6)

C2—O2—C3	116.23 (5)	CD1—CG—CB	121.60 (3)
C—N—CA	121.36 (4)	CD2—CG—CB	120.49 (3)
N—CA—C2	110.35 (3)	CG—CD1—CE1	121.40 (4)
N—CA—CB	110.85 (3)	O2—C3—C4	108.05 (4)
C2—CA—CB	109.77 (3)	CG—CB—CA	113.10 (3)
O—C—N	122.42 (5)	CE1—CZ—OH	122.57 (4)
O—C—C1	121.71 (5)	CE1—CZ—CE2	119.71 (4)
N—C—C1	115.87 (4)	OH—CZ—CE2	117.71 (4)
O1—C2—O2	124.27 (5)	CZ—CE2—CD2	119.70 (4)
O1—C2—CA	124.37 (4)	CZ—CE1—CD1	119.74 (3)
O2—C2—CA	111.36 (4)	CG—CD2—CE2	121.53 (4)
CD1—CG—CD2	117.91 (3)

O2—C2—CA—N	−167.3 (3)	CD1—CG—CB—CA	64.53 (5)
O1—C2—CA—N	13.34 (6)	CD2—CG—CB—CA	−116.17 (4)
CG—CB—CA—N	63.05 (4)	C—N—CA—C2	74.16 (4)

Hydrogen-bond geometry (Å, º) for (110) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HW2···O1	.9647 (5)	2.0097 (5)	2.9420 (7)	161.93 (3)
OW—HW1···Oⁱ	.9652 (6)	1.8280 (6)	2.7863 (8)	171.51 (3)
OH—HH···OWⁱⁱ	.9675 (6)	1.7312 (4)	2.6912 (7)	171.10 (3)
N—H···OHⁱⁱⁱ	1.0321 (5)	1.9454 (5)	2.9640 (7)	168.51 (2)

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

Selected geometric parameters (Å, º) for (293) top

O1—C2	1.203 (2)	C—C1	1.507 (3)
O—C	1.225 (2)	CG—CD1	1.384 (3)
O2—C2	1.316 (2)	CG—CD2	1.384 (3)
O2—C3	1.463 (2)	CG—CB	1.516 (2)
OH—CZ	1.381 (2)	CD1—CE1	1.392 (3)
N—C	1.345 (3)	C3—C4	1.462 (4)
N—CA	1.451 (2)	CZ—CE1	1.379 (3)
CA—C2	1.523 (2)	CZ—CE2	1.383 (3)
CA—CB	1.535 (3)	CE2—CD2	1.385 (3)

C2—O2—C3	116.7 (2)	CD1—CG—CB	122.1 (2)
C—N—CA	121.7 (2)	CD2—CG—CB	120.4 (2)
N—CA—C2	110.17 (14)	CG—CD1—CE1	121.9 (2)
N—CA—CB	111.37 (14)	O2—C3—C4	108.8 (2)
C2—CA—CB	109.91 (14)	CG—CB—CA	113.78 (15)
O—C—N	122.4 (2)	CE1—CZ—OH	122.5 (2)
O—C—C1	121.8 (2)	CE1—CZ—CE2	119.8 (2)
N—C—C1	115.8 (2)	OH—CZ—CE2	117.7 (2)
O1—C2—O2	123.5 (2)	CZ—CE2—CD2	119.9 (2)
O1—C2—CA	125.04 (15)	CZ—CE1—CD1	119.3 (2)
O2—C2—CA	111.42 (14)	CG—CD2—CE2	121.5 (2)
CD1—CG—CD2	117.5 (2)

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