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The electron density and electrostatic properties of Tyr-Gly-Gly and Gly-Asp molecules have been determined from high-resolution X-ray diffraction data at 123 K. Topological properties of the charge distribution are discussed and compared with those derived from other experimental studies on peptide molecules, and the characteristics of the (3,−1) critical points of the C=O, C—N, C—C bonds are analysed. Crystal data for Tyr-Gly-Gly: C13H17N3O5·H2O, Mr = 313, orthorhombic, P212121, Z = 4, T = 123 ± 2 K; lattice parameters: a = 7.984 (2), b = 9.535 (3), c = 18.352 (5) Å, V = 1397.1 (6) Å3, Dx = 1.49 g cm−3, μ = 1.2 cm−1 for λMo = 0.7107 Å. Crystal data for Gly-Asp: C6H10N2O5·2H2O, Mr = 212, orthorhombic, P212121, Z = 4, T = 123 ± 2 K; lattice parameters: a = 9.659 (1), b = 9.672 (1), c = 10.739 (1) Å, V = 1003.3 (4) Å3, Dx = 1.40 g cm−3, μ = 1.3 cm−1 for λMo = 0.7107 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100004390/bs0010sup1.cif
Contains datablocks global, YGG, GD

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100004390/bs0010YGGsup2.hkl
Contains datablock YGG

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100004390/bs0010GDsup3.hkl
Contains datablock GD

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768100004390/bs0010sup4.pdf
Supplementary material

CCDC references: 148925; 148926

Computing details top

(YGG) top
Crystal data top
C13H17N3O5·H2Oc = 18.352 (5) Å
Mr = 313V = 1397.1 (6) Å3
Orthorhombic, P212121Z = 4
a = 7.984 (2) ÅDx = 1.49 Mg m3
b = 9.535 (3) ÅMo Kα radiation, λ = 0.7107 Å
Data collection top
h = l =
k =
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.29679 (6)0.38515 (6)0.05665 (3)0.015 (1)
O20.14819 (7)0.49680 (6)0.14781 (2)0.014 (1)
O310.21920 (6)0.99642 (5)0.11764 (3)0.014 (1)
O320.00356 (7)0.85722 (5)0.13385 (3)0.015 (1)
OH10.22461 (7)0.22641 (5)0.08568 (3)0.019 (1)
O60.07754 (7)0.22615 (5)0.18999 (3)0.016 (1)
N10.30502 (7)0.43883 (6)0.19877 (3)0.012 (1)
N20.02553 (7)0.44865 (6)0.04149 (3)0.011 (1)
N30.15617 (8)0.64654 (6)0.05190 (3)0.013 (1)
C10.16215 (9)0.42107 (7)0.08231 (3)0.010 (1)
C1A0.13657 (9)0.43357 (7)0.16456 (3)0.011 (1)
C1B0.03320 (9)0.30932 (7)0.19391 (4)0.012 (1)
C20.11734 (8)0.52464 (7)0.08310 (4)0.011 (1)
C2A0.02899 (9)0.41640 (7)0.03566 (3)0.012 (1)
C3A0.24986 (9)0.75644 (7)0.08749 (4)0.014 (1)
C30.14502 (9)0.88070 (7)0.11413 (3)0.011 (1)
C1G0.08635 (9)0.16721 (7)0.16566 (4)0.011 (1)
C1E10.25135 (9)0.04652 (7)0.17721 (4)0.013 (1)
C1D10.20376 (9)0.08535 (7)0.20273 (3)0.013 (1)
C1Z0.18290 (9)0.09706 (7)0.11268 (4)0.013 (1)
C1D20.01886 (9)0.11386 (7)0.10092 (4)0.013 (1)
C1E20.06705 (9)0.01667 (8)0.07405 (4)0.013 (1)
H1A0.070060.529550.177070.014 (4)
H1B10.044230.310950.252880.016 (4)
H1B20.096210.326770.179250.016 (4)
H2A10.091480.317840.047810.016 (4)
H2A20.099680.407700.053970.016 (4)
H3A10.309660.718770.136720.018 (4)
H3A20.341610.797950.049320.018 (4)
HN110.383150.515810.178370.016 (4)
HN120.375130.349970.188610.016 (4)
HN130.298030.444930.254720.016 (4)
HN20.088520.468270.065680.016 (4)
HN30.131140.663680.002310.016 (4)
H1D10.259650.123560.251960.017 (4)
H1E10.342880.107830.205360.017 (4)
H1D20.067140.175240.069340.017 (4)
H1E20.021530.059450.023740.017 (4)
HO50.329020.261320.104730.015 (4)
HW10.129950.157040.159160.021 (5)
HW20.106140.319060.173560.021 (5)
Geometric parameters (Å, º) top
N1—C1A1.4851 (9)C2A—C21.5233 (9)
C1A—C1B1.5409 (9)C2—O21.2416 (8)
C1B—C1G1.5115 (10)C2—N31.3322 (9)
C1G—C1D11.3967 (10)N3—C3A1.4436 (9)
C1G—C1D21.4002 (9)C3A—C31.5307 (10)
C1D1—C1E11.3945 (10)C3—O311.2539 (9)
C1D2—C1E21.3929 (10)C3—O321.2603 (9)
C1E1—C1Z1.3904 (10)O6—HW10.9640 (5)
C1E2—C1Z1.3949 (10)O6—HW20.9632 (5)
C1Z—OH11.3701 (9)OH1—HO50.9633 (6)
C1A—C11.5280 (9)N1—HN111.0334 (6)
C1—O11.2225 (9)N1—HN121.0324 (6)
C1—N21.3491 (9)N1—HN131.0300 (6)
N2—C2A1.4492 (8)
N1—C1A—C1107.41 (5)C3A—C3—O32117.97 (6)
N1—C1A—C1B111.30 (6)O31—C3—O32125.88 (7)
C1A—C1—O1121.33 (6)C1A—C1B—C1G114.77 (6)
C1A—C1—N2115.17 (6)C1B—C1G—C1D1121.49 (6)
O1—C1—N2123.48 (6)C1B—C1G—C1D2120.57 (6)
C1—N2—C2A119.06 (6)C1G—C1D1—C1E1121.54 (6)
C1—C1A—C1B110.91 (6)C1G—C1D2—C1E2121.25 (7)
N2—C2A—C2115.05 (6)C1D1—C1E1—C1Z119.44 (7)
C2A—C2—O2119.58 (6)C1D2—C1E2—C1Z119.62 (7)
C2A—C2—N3116.95 (6)C1E1—C1Z—C1E2120.20 (7)
O2—C2—N3123.46 (7)C1E1—C1Z—OH1121.63 (6)
C2—N3—C3A124.02 (6)C1E2—C1Z—OH1118.16 (6)
N3—C3A—C3115.02 (6)HW1—O6—HW2110.00 (5)
C3A—C3—O31116.05 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AH···AD···AD—H···A
O6—HW2···O21.792.7525 (7)176
N1—HN13···O2i1.922.9057 (7)159
N2—HN2···O31ii1.842.8652 (8)174
O6—HW1···O31iii1.852.8000 (7)167
OH1—HO5···O32iv1.702.6547 (9)168
N1—HN11···O32v1.722.7453 (9)172
N3—HN3···OH1vi2.002.8534 (8)139
N1—HN12···O6iv1.772.6898 (9)146
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x1/2, y+3/2, z; (iii) x, y1, z; (iv) x+1/2, y+1/2, z; (v) x+1/2, y+3/2, z; (vi) x, y+1, z.
(GD) top
Crystal data top
C6H10N2O5·2(H2O)c = 10.739 (1) Å
Mr = 212V = 1003.3 (4) Å3
Orthorhombic, P212121Z = 4
a = 9.659 (1) ÅDx = 1.40 Mg m3
b = 9.672 (1) ÅMo Kα radiation, λ = 0.7107 Å
Data collection top
h = l =
k =
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O210.78621 (4)0.27464 (4)0.22757 (4)0.015 (1)
O220.94748 (4)0.14220 (4)0.31605 (4)0.017 (1)
C20.82426 (5)0.16995 (5)0.28803 (5)0.012 (1)
C2A0.71303 (5)0.06645 (5)0.32942 (5)0.013 (1)
N20.57674 (4)0.11497 (4)0.29271 (5)0.014 (1)
C10.48454 (5)0.03277 (5)0.23657 (4)0.012 (1)
O10.50751 (4)0.08792 (4)0.20603 (4)0.018 (1)
C1A0.34498 (5)0.10086 (5)0.21273 (5)0.015 (1)
N10.26556 (5)0.01730 (5)0.12333 (5)0.015 (1)
C2B0.71587 (6)0.03553 (5)0.46976 (5)0.016 (1)
C2G0.67069 (5)0.16118 (5)0.54215 (5)0.014 (1)
O2D10.71240 (5)0.27664 (4)0.51789 (4)0.019 (1)
O2D20.58222 (5)0.13440 (4)0.63233 (5)0.022 (1)
OW10.95007 (4)0.41590 (4)0.06995 (4)0.018 (1)
OW20.39866 (5)0.19248 (5)0.48429 (5)0.024 (1)
H2A0.74147 (3)0.02974 (3)0.28281 (3)0.016 (6)
HN20.54291 (3)0.21517 (3)0.30427 (3)0.019 (6)
H1A10.36615 (3)0.20362 (3)0.17549 (3)0.020 (6)
H1A20.29585 (3)0.10799 (3)0.30204 (3)0.020 (7)
HN110.32591 (3)0.00694 (3)0.04364 (3)0.020 (7)
HN120.17890 (3)0.07177 (3)0.09329 (3)0.020 (6)
HN130.24809 (3)0.07590 (3)0.16559 (3)0.020 (6)
H2B10.82348 (3)0.02143 (3)0.49598 (3)0.021 (7)
H2B20.64005 (3)0.04544 (3)0.48652 (3)0.021 (6)
HD220.54140 (4)0.21932 (4)0.66273 (3)0.030 (8)
HW110.89563 (3)0.36954 (3)0.13191 (3)0.024 (7)
HW121.00414 (3)0.48600 (3)0.11074 (3)0.024 (7)
HW210.34677 (4)0.21581 (3)0.41107 (3)0.031 (8)
HW220.44338 (3)0.27255 (4)0.51934 (3)0.031 (8)
Geometric parameters (Å, º) top
N1—C1A1.4705 (7)C2B—C2G1.5069 (7)
C1A—C11.5219 (7)C2G—O2D11.2159 (6)
C1—O11.2327 (6)C2G—O2D21.3168 (7)
C1—N21.3373 (7)O2D2—HD220.9604 (4)
N2—C2A1.4520 (7)OW1—HW110.9647 (4)
C2A—C21.5346 (7)OW1—HW120.9612 (4)
C2—O211.2576 (6)OW2—HW210.9625 (5)
C2—O221.2567 (6)OW2—HW220.9713 (5)
C2A—C2B1.5367 (7)
N1—C1A—C1109.53 (4)O21—C2—O22124.91 (5)
C1A—C1—O1121.61 (5)C2A—C2B—C2G110.12 (4)
C1A—C1—N2114.13 (4)C2B—C2G—O2D1122.27 (5)
O1—C1—N2124.26 (5)C2B—C2G—O2D2114.15 (4)
C1—N2—C2A122.25 (4)O2D1—C2G—O2D2123.58 (5)
N2—C2A—C2110.17 (4)C2G—O2D2—HD22110.11 (4)
N2—C2A—C2B110.23 (4)HW11—OW1—HW12108.10 (4)
C2A—C2—O21118.07 (4)HW21—OW2—HW22111.43 (5)
C2A—C2—O22117.02 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AH···AD···AD—H···A
OW1—HW11···O211.732.6905 (6)172
N1—HN13···O21i1.862.8852 (7)170
OD22—HD22···O22ii1.642.5826 (6)167
OW1—HW12···O22iii1.772.6960 (6)162
N2—HN2···O1iv1.972.9875 (6)167
OW2—HW22···OW1v1.812.7666 (7)172
N1—HN11···OW1vi1.872.8110 (7)150
N1—HN12···OW2vii1.832.7595 (7)147
OW2—HW21···O21i1.962.9100 (7)166
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1/2, y1/2, z1; (iii) x+2, y1/2, z1/2; (iv) x1, y1/2, z1/2; (v) x+5/2, y, z1/2; (vi) x+1/2, y1/2, z; (vii) x1/2, y, z+1/2.
 

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