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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.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks 110, 293, global

hkl

Structure factor file (CIF format)
Contains datablock 110

hkl

Structure factor file (CIF format)
Contains datablock pepabs

pdf

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
[Figure 1]
[Figure 2]
(110) N-Acetyl-L-tyrosine Ethyl Ester Monohydrate top
Crystal data top
C13H17NO4·H2ODx = 1.313 Mg m3
Mr = 269.29Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 512 reflections
a = 7.235 (2) Åθ = 11–45°
b = 13.056 (4) ŵ = 0.10 mm1
c = 14.415 (4) ÅT = 110 K
V = 1361.6 (12) Å3Prism, colourless
Z = 40.3 × 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 tubeRint = 0.027
Graphite monochromatorθmax = 51.1°, θmin = 2.1°
ω scanh = 1515
98393 measured reflectionsk = 2828
14787 independent reflectionsl = 3131
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.027Calculated w = 1/[σ2(Fo2)]
wR(F2) = 0.0202(Δ/σ)max = 0.006
10189 reflectionsΔρmax = 0.14 e Å3
544 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1.63 (115)
Secondary atom site location: difference Fourier map
Crystal data top
C13H17NO4·H2OV = 1361.6 (12) Å3
Mr = 269.29Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.235 (2) ŵ = 0.10 mm1
b = 13.056 (4) ÅT = 110 K
c = 14.415 (4) Å0.3 × 0.2 × 0.2 mm
Data collection top
Siemens SMART-CCD
diffractometer
10189 reflections with I > 2σ(I)
98393 measured reflectionsRint = 0.027
14787 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027All H-atom parameters refined
wR(F2) = 0.0202Δρmax = 0.14 e Å3
10189 reflectionsΔρmin = 0.17 e Å3
544 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
0 restraintsAbsolute 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
xyzUiso*/Ueq
O10.23164 (13)0.20571 (4)0.42334 (4)0.0201 (1)
O0.57804 (8)0.03798 (4)0.37422 (5)0.0170 (1)
O20.19614 (9)0.12871 (4)0.56155 (4)0.0149 (1)
OH0.02619 (10)0.44263 (4)0.32345 (4)0.0185 (1)
HH0.031 (4)0.491 (2)0.364 (2)0.023 (2)*
N0.27588 (7)0.01970 (3)0.33598 (3)0.0123 (1)
H0.178 (4)0.024 (4)0.284 (2)0.0154 (19)*
CA0.21351 (6)0.01977 (3)0.43117 (3)0.0109 (1)
HA0.311 (2)0.024 (2)0.472 (2)0.0137 (17)*
C0.45551 (7)0.03238 (3)0.31432 (3)0.0128 (1)
C20.21534 (6)0.12880 (3)0.47020 (3)0.0118 (1)
CG0.00760 (7)0.13705 (3)0.40996 (3)0.0124 (1)
CD10.10085 (7)0.21384 (4)0.45900 (3)0.0149 (1)
HD10.185 (4)0.193 (2)0.517 (2)0.019 (2)*
C30.20187 (9)0.22828 (4)0.60674 (4)0.0178 (1)
H310.094 (4)0.273 (2)0.573 (2)0.022 (2)*
H320.336 (4)0.262 (2)0.593 (2)0.022 (2)*
CB0.01763 (6)0.02579 (3)0.43907 (3)0.0134 (1)
HB10.026 (5)0.016 (2)0.510 (2)0.0168 (16)*
HB20.076 (4)0.021 (2)0.398 (2)0.0168 (16)*
C10.49913 (8)0.04026 (4)0.21235 (3)0.0205 (1)
H110.636 (5)0.011 (3)0.198 (2)0.025 (3)*
H120.494 (5)0.121 (3)0.194 (2)0.025 (3)*
H130.392 (5)0.006 (3)0.169 (2)0.025 (3)*
CZ0.01333 (7)0.34367 (4)0.35433 (3)0.0136 (1)
CE20.10879 (8)0.26824 (4)0.30497 (4)0.0178 (1)
HE20.187 (4)0.288 (2)0.244 (2)0.022 (2)*
CE10.09113 (7)0.31631 (3)0.43194 (3)0.0148 (1)
HE10.161 (4)0.375 (2)0.470 (2)0.019 (2)*
CD20.09781 (7)0.16620 (3)0.33312 (3)0.0165 (1)
HD20.171 (2)0.107 (2)0.295 (2)0.021 (2)*
C40.16687 (10)0.21257 (4)0.70827 (4)0.0260 (1)
H410.199 (4)0.284 (2)0.743 (2)0.031 (2)*
H420.255 (4)0.154 (2)0.737 (2)0.031 (2)*
H430.024 (4)0.190 (2)0.720 (2)0.031 (2)*
OW0.14436 (8)0.42520 (4)0.43837 (4)0.0191 (1)
HW10.118 (4)0.432 (2)0.504 (2)0.024 (2)*
HW20.158 (4)0.353 (2)0.426 (2)0.024 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0355 (3)0.01068 (15)0.01406 (18)0.00118 (18)0.00384 (19)0.00146 (14)
O0.01324 (19)0.0218 (2)0.01590 (18)0.00126 (16)0.00122 (16)0.00271 (15)
O20.0239 (2)0.00970 (14)0.01103 (17)0.00023 (16)0.00065 (16)0.00136 (13)
OH0.0253 (3)0.01128 (16)0.0184 (2)0.00086 (16)0.00888 (19)0.00171 (14)
N0.01215 (16)0.01438 (15)0.01019 (14)0.00012 (13)0.00041 (13)0.00168 (11)
CA0.01200 (14)0.01000 (12)0.01083 (13)0.00071 (11)0.00016 (12)0.00123 (10)
C0.01322 (17)0.01359 (16)0.01150 (15)0.00102 (12)0.00057 (13)0.00267 (12)
C20.01517 (17)0.00907 (13)0.01110 (14)0.00049 (12)0.00059 (12)0.00043 (11)
CG0.01322 (17)0.01120 (14)0.01278 (15)0.00057 (12)0.00120 (14)0.00101 (11)
CD10.01795 (19)0.01264 (16)0.01410 (15)0.0007 (14)0.00543 (15)0.00081 (12)
C30.0280 (3)0.01063 (14)0.01487 (17)0.00054 (15)0.00045 (17)0.00248 (13)
CB0.01228 (15)0.01213 (14)0.01579 (15)0.00010 (12)0.00099 (12)0.00257 (12)
C10.0227 (2)0.0254 (2)0.01337 (16)0.00591 (17)0.00452 (15)0.00347 (14)
CZ0.01665 (19)0.01093 (15)0.01327 (16)0.00017 (14)0.00403 (15)0.00068 (12)
CE20.0242 (2)0.01213 (16)0.01714 (18)0.00123 (15)0.01004 (17)0.00136 (14)
CE10.01790 (17)0.01205 (14)0.01452 (16)0.00029 (16)0.00571 (15)0.00006 (12)
CD20.02070 (19)0.01174 (15)0.01705 (17)0.00096 (14)0.00726 (16)0.00062 (13)
C40.0487 (4)0.01736 (18)0.01260 (17)0.0064 (2)0.00312 (19)0.00303 (14)
OW0.0274 (2)0.01407 (16)0.01584 (19)0.00282 (15)0.00161 (16)0.00180 (13)
Geometric parameters (Å, º) top
O1—C21.2160 (6)C—C11.5086 (6)
O—C1.2390 (7)CG—CD11.4001 (6)
O2—C21.3237 (7)CG—CD21.3968 (6)
O2—C31.4545 (7)CG—CB1.5144 (5)
OH—CZ1.3697 (6)CD1—CE11.3960 (6)
N—C1.3475 (7)C3—C41.5008 (7)
N—CA1.4444 (6)CZ—CE11.3965 (6)
CA—C21.5307 (5)CZ—CE21.3984 (6)
CA—CB1.5422 (6)CE2—CD21.3948 (6)
C2—O2—C3116.23 (5)CD1—CG—CB121.60 (3)
C—N—CA121.36 (4)CD2—CG—CB120.49 (3)
N—CA—C2110.35 (3)CG—CD1—CE1121.40 (4)
N—CA—CB110.85 (3)O2—C3—C4108.05 (4)
C2—CA—CB109.77 (3)CG—CB—CA113.10 (3)
O—C—N122.42 (5)CE1—CZ—OH122.57 (4)
O—C—C1121.71 (5)CE1—CZ—CE2119.71 (4)
N—C—C1115.87 (4)OH—CZ—CE2117.71 (4)
O1—C2—O2124.27 (5)CZ—CE2—CD2119.70 (4)
O1—C2—CA124.37 (4)CZ—CE1—CD1119.74 (3)
O2—C2—CA111.36 (4)CG—CD2—CE2121.53 (4)
CD1—CG—CD2117.91 (3)
O2—C2—CA—N167.3 (3)CD1—CG—CB—CA64.53 (5)
O1—C2—CA—N13.34 (6)CD2—CG—CB—CA116.17 (4)
CG—CB—CA—N63.05 (4)C—N—CA—C274.16 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW—HW2···O10.9647 (5)2.0097 (5)2.9420 (7)161.93 (3)
OW—HW1···Oi0.9652 (6)1.8280 (6)2.7863 (8)171.51 (3)
OH—HH···OWii0.9675 (6)1.7312 (4)2.6912 (7)171.10 (3)
N—H···OHiii1.0321 (5)1.9454 (5)2.9640 (7)168.51 (2)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x, y1, z; (iii) x, y+1/2, z+1/2.
(293) N-Acetyl-L-tyrosine Ethyl Ester Monohydrate top
Crystal data top
C13H17NO4·H2ODx = 1.270 Mg m3
Mr = 269.29Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 411 reflections
a = 7.3827 (2) Åθ = 11–45°
b = 13.1421 (4) ŵ = 0.10 mm1
c = 14.5150 (4) ÅT = 293 K
V = 1408.31 (7) Å3Prism, colourless
Z = 40.3 × 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 tubeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
ω scansh = 99
15638 measured reflectionsk = 1717
3241 independent reflectionsl = 1818
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.038Calculated w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2434P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max = 0.006
S = 1.10Δρmax = 0.17 e Å3
3238 reflectionsΔρmin = 0.16 e Å3
249 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.044 (33)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 1.63 (115)
Crystal data top
C13H17NO4·H2OV = 1408.31 (7) Å3
Mr = 269.29Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.3827 (2) ŵ = 0.10 mm1
b = 13.1421 (4) ÅT = 293 K
c = 14.5150 (4) Å0.3 × 0.2 × 0.2 mm
Data collection top
Siemens SMART-CCD
diffractometer
2660 reflections with I > 2σ(I)
15638 measured reflectionsRint = 0.032
3241 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038All H-atom parameters refined
wR(F2) = 0.100Δρmax = 0.17 e Å3
S = 1.10Δρmin = 0.16 e Å3
3238 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
249 parametersAbsolute 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.

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
xyzUiso*/Ueq
O10.2154 (3)0.20331 (10)0.42472 (10)0.0653 (5)
O0.5662 (2)0.03510 (13)0.38004 (10)0.0544 (4)
O20.1893 (2)0.12768 (9)0.56078 (9)0.0544 (4)
OH0.0282 (2)0.44010 (11)0.32293 (11)0.0588 (4)
HH0.022 (4)0.480 (2)0.3613 (18)0.067 (8)*
N0.2735 (2)0.01902 (12)0.33857 (10)0.0385 (3)
H0.193 (3)0.0227 (18)0.2935 (16)0.054 (6)*
CA0.2063 (2)0.01927 (13)0.43251 (11)0.0357 (4)
HA0.287 (3)0.0193 (14)0.4701 (12)0.031 (4)*
C0.4507 (3)0.03053 (15)0.31956 (13)0.0432 (4)
C20.2049 (3)0.12727 (13)0.47049 (12)0.0392 (4)
CG0.0064 (3)0.13737 (13)0.40918 (12)0.0384 (4)
CD10.0981 (3)0.21311 (15)0.45619 (14)0.0477 (5)
HD10.176 (4)0.1962 (19)0.5062 (17)0.062 (7)*
C30.1894 (5)0.2273 (2)0.6058 (2)0.0703 (8)
H310.100 (4)0.268 (2)0.5733 (19)0.072 (8)*
H320.311 (4)0.2426 (19)0.6403 (18)0.062 (7)*
CB0.0156 (3)0.02671 (14)0.43830 (14)0.0432 (4)
HB10.023 (3)0.0167 (17)0.5058 (15)0.053 (6)*
HB20.072 (3)0.0137 (17)0.4001 (14)0.049 (6)*
C10.4987 (4)0.0390 (3)0.2190 (2)0.0659 (7)
H110.588 (6)0.004 (3)0.207 (3)0.118 (13)*
H120.503 (6)0.108 (4)0.206 (3)0.138 (15)*
H130.397 (5)0.016 (3)0.177 (3)0.113 (12)*
CZ0.0153 (3)0.34118 (13)0.35436 (12)0.0417 (4)
CE20.1098 (3)0.2670 (2)0.3069 (2)0.0556 (6)
HE20.175 (3)0.2823 (18)0.2529 (17)0.062 (7)*
CE10.0886 (3)0.31474 (15)0.42960 (14)0.0463 (5)
HE10.152 (3)0.3627 (19)0.4637 (17)0.058 (6)*
CD20.0986 (3)0.1663 (2)0.3347 (2)0.0515 (5)
HD20.160 (3)0.1110 (19)0.3009 (15)0.056 (6)*
C40.1647 (9)0.2127 (3)0.7049 (2)0.127 (2)
H410.191 (5)0.285 (3)0.735 (3)0.119 (12)*
H420.207 (6)0.157 (3)0.732 (3)0.121 (13)*
H430.020 (18)0.207 (8)0.664 (7)0.38 (6)*
OW0.1445 (2)0.42672 (13)0.43466 (12)0.0586 (4)
HW10.114 (5)0.436 (3)0.499 (3)0.100 (11)*
HW20.151 (5)0.369 (3)0.427 (3)0.105 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1149 (14)0.0330 (7)0.0479 (8)0.0033 (8)0.0047 (9)0.0024 (6)
O0.0426 (7)0.0668 (9)0.0538 (8)0.0027 (7)0.0049 (6)0.0095 (7)
O20.0910 (11)0.0333 (7)0.0388 (7)0.0039 (7)0.0023 (7)0.0058 (6)
OH0.0830 (12)0.0367 (7)0.0565 (9)0.0013 (7)0.0253 (8)0.0033 (6)
N0.0396 (8)0.0411 (8)0.0348 (7)0.0005 (7)0.0014 (6)0.0050 (6)
CA0.0387 (9)0.0331 (8)0.0353 (8)0.0029 (7)0.0021 (7)0.0037 (7)
C0.0462 (11)0.0386 (9)0.0448 (10)0.0005 (8)0.0014 (8)0.0106 (8)
C20.0453 (10)0.0335 (9)0.0388 (9)0.0031 (8)0.0009 (8)0.0019 (7)
CG0.0370 (9)0.0364 (8)0.0419 (9)0.0024 (7)0.0029 (7)0.0015 (7)
CD10.0547 (12)0.0438 (11)0.0445 (10)0.0049 (9)0.0138 (9)0.0012 (8)
C30.120 (2)0.0390 (11)0.0517 (13)0.0136 (14)0.0104 (15)0.0148 (9)
CB0.0409 (10)0.0385 (9)0.0503 (10)0.0018 (8)0.0029 (9)0.0067 (9)
C10.067 (2)0.084 (2)0.0470 (12)0.013 (2)0.0126 (12)0.0142 (12)
CZ0.0477 (10)0.0348 (9)0.0425 (9)0.0023 (8)0.0070 (8)0.0017 (7)
CE20.0703 (14)0.0426 (11)0.0537 (12)0.0010 (10)0.0273 (11)0.0023 (9)
CE10.0514 (11)0.0388 (9)0.0486 (11)0.0002 (8)0.0135 (9)0.0037 (9)
CD20.0608 (13)0.0376 (10)0.0560 (12)0.0039 (9)0.0190 (10)0.0024 (9)
C40.261 (6)0.061 (2)0.058 (2)0.038 (3)0.036 (3)0.0150 (14)
OW0.0825 (12)0.0421 (8)0.0512 (9)0.0050 (8)0.0045 (8)0.0037 (7)
Geometric parameters (Å, º) top
O1—C21.203 (2)C—C11.507 (3)
O—C1.225 (2)CG—CD11.384 (3)
O2—C21.316 (2)CG—CD21.384 (3)
O2—C31.463 (2)CG—CB1.516 (2)
OH—CZ1.381 (2)CD1—CE11.392 (3)
N—C1.345 (3)C3—C41.462 (4)
N—CA1.451 (2)CZ—CE11.379 (3)
CA—C21.523 (2)CZ—CE21.383 (3)
CA—CB1.535 (3)CE2—CD21.385 (3)
C2—O2—C3116.7 (2)CD1—CG—CB122.1 (2)
C—N—CA121.7 (2)CD2—CG—CB120.4 (2)
N—CA—C2110.17 (14)CG—CD1—CE1121.9 (2)
N—CA—CB111.37 (14)O2—C3—C4108.8 (2)
C2—CA—CB109.91 (14)CG—CB—CA113.78 (15)
O—C—N122.4 (2)CE1—CZ—OH122.5 (2)
O—C—C1121.8 (2)CE1—CZ—CE2119.8 (2)
N—C—C1115.8 (2)OH—CZ—CE2117.7 (2)
O1—C2—O2123.5 (2)CZ—CE2—CD2119.9 (2)
O1—C2—CA125.04 (15)CZ—CE1—CD1119.3 (2)
O2—C2—CA111.42 (14)CG—CD2—CE2121.5 (2)
CD1—CG—CD2117.5 (2)

Experimental details

(110)(293)
Crystal data
Chemical formulaC13H17NO4·H2OC13H17NO4·H2O
Mr269.29269.29
Crystal system, space groupOrthorhombic, P212121Orthorhombic, P212121
Temperature (K)110293
a, b, c (Å)7.235 (2), 13.056 (4), 14.415 (4)7.3827 (2), 13.1421 (4), 14.5150 (4)
V3)1361.6 (12)1408.31 (7)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.100.10
Crystal size (mm)0.3 × 0.2 × 0.20.3 × 0.2 × 0.2
Data collection
DiffractometerSiemens 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
Rint0.0270.032
(sin θ/λ)max1)1.0950.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.0202, ? 0.038, 0.100, 1.10
No. of reflections101893238
No. of parameters544249
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.14, 0.170.17, 0.16
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter1.63 (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—C21.2160 (6)C—C11.5086 (6)
O—C1.2390 (7)CG—CD11.4001 (6)
O2—C21.3237 (7)CG—CD21.3968 (6)
O2—C31.4545 (7)CG—CB1.5144 (5)
OH—CZ1.3697 (6)CD1—CE11.3960 (6)
N—C1.3475 (7)C3—C41.5008 (7)
N—CA1.4444 (6)CZ—CE11.3965 (6)
CA—C21.5307 (5)CZ—CE21.3984 (6)
CA—CB1.5422 (6)CE2—CD21.3948 (6)
C2—O2—C3116.23 (5)CD1—CG—CB121.60 (3)
C—N—CA121.36 (4)CD2—CG—CB120.49 (3)
N—CA—C2110.35 (3)CG—CD1—CE1121.40 (4)
N—CA—CB110.85 (3)O2—C3—C4108.05 (4)
C2—CA—CB109.77 (3)CG—CB—CA113.10 (3)
O—C—N122.42 (5)CE1—CZ—OH122.57 (4)
O—C—C1121.71 (5)CE1—CZ—CE2119.71 (4)
N—C—C1115.87 (4)OH—CZ—CE2117.71 (4)
O1—C2—O2124.27 (5)CZ—CE2—CD2119.70 (4)
O1—C2—CA124.37 (4)CZ—CE1—CD1119.74 (3)
O2—C2—CA111.36 (4)CG—CD2—CE2121.53 (4)
CD1—CG—CD2117.91 (3)
O2—C2—CA—N167.3 (3)CD1—CG—CB—CA64.53 (5)
O1—C2—CA—N13.34 (6)CD2—CG—CB—CA116.17 (4)
CG—CB—CA—N63.05 (4)C—N—CA—C274.16 (4)
Hydrogen-bond geometry (Å, º) for (110) top
D—H···AD—HH···AD···AD—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···OHiii1.0321 (5)1.9454 (5)2.9640 (7)168.51 (2)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x, y1, z; (iii) x, y+1/2, z+1/2.
Selected geometric parameters (Å, º) for (293) top
O1—C21.203 (2)C—C11.507 (3)
O—C1.225 (2)CG—CD11.384 (3)
O2—C21.316 (2)CG—CD21.384 (3)
O2—C31.463 (2)CG—CB1.516 (2)
OH—CZ1.381 (2)CD1—CE11.392 (3)
N—C1.345 (3)C3—C41.462 (4)
N—CA1.451 (2)CZ—CE11.379 (3)
CA—C21.523 (2)CZ—CE21.383 (3)
CA—CB1.535 (3)CE2—CD21.385 (3)
C2—O2—C3116.7 (2)CD1—CG—CB122.1 (2)
C—N—CA121.7 (2)CD2—CG—CB120.4 (2)
N—CA—C2110.17 (14)CG—CD1—CE1121.9 (2)
N—CA—CB111.37 (14)O2—C3—C4108.8 (2)
C2—CA—CB109.91 (14)CG—CB—CA113.78 (15)
O—C—N122.4 (2)CE1—CZ—OH122.5 (2)
O—C—C1121.8 (2)CE1—CZ—CE2119.8 (2)
N—C—C1115.8 (2)OH—CZ—CE2117.7 (2)
O1—C2—O2123.5 (2)CZ—CE2—CD2119.9 (2)
O1—C2—CA125.04 (15)CZ—CE1—CD1119.3 (2)
O2—C2—CA111.42 (14)CG—CD2—CE2121.5 (2)
CD1—CG—CD2117.5 (2)
 

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