research papers
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100004390/bs0010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100004390/bs0010YGGsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100004390/bs0010GDsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768100004390/bs0010sup4.pdf |
CCDC references: 148925; 148926
Computing details top
(YGG) top
Crystal data top
C13H17N3O5·H2O | c = 18.352 (5) Å |
Mr = 313 | V = 1397.1 (6) Å3 |
Orthorhombic, P212121 | Z = 4 |
a = 7.984 (2) Å | Dx = 1.49 Mg m−3 |
b = 9.535 (3) Å | Mo Kα radiation, λ = 0.7107 Å |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.29679 (6) | 0.38515 (6) | −0.05665 (3) | 0.015 (1) | |
O2 | 0.14819 (7) | 0.49680 (6) | 0.14781 (2) | 0.014 (1) | |
O31 | 0.21920 (6) | 0.99642 (5) | 0.11764 (3) | 0.014 (1) | |
O32 | −0.00356 (7) | 0.85722 (5) | 0.13385 (3) | 0.015 (1) | |
OH1 | 0.22461 (7) | −0.22641 (5) | −0.08568 (3) | 0.019 (1) | |
O6 | 0.07754 (7) | 0.22615 (5) | 0.18999 (3) | 0.016 (1) | |
N1 | 0.30502 (7) | 0.43883 (6) | −0.19877 (3) | 0.012 (1) | |
N2 | 0.02553 (7) | 0.44865 (6) | −0.04149 (3) | 0.011 (1) | |
N3 | 0.15617 (8) | 0.64654 (6) | 0.05190 (3) | 0.013 (1) | |
C1 | 0.16215 (9) | 0.42107 (7) | −0.08231 (3) | 0.010 (1) | |
C1A | 0.13657 (9) | 0.43357 (7) | −0.16456 (3) | 0.011 (1) | |
C1B | 0.03320 (9) | 0.30932 (7) | −0.19391 (4) | 0.012 (1) | |
C2 | 0.11734 (8) | 0.52464 (7) | 0.08310 (4) | 0.011 (1) | |
C2A | 0.02899 (9) | 0.41640 (7) | 0.03566 (3) | 0.012 (1) | |
C3A | 0.24986 (9) | 0.75644 (7) | 0.08749 (4) | 0.014 (1) | |
C3 | 0.14502 (9) | 0.88070 (7) | 0.11413 (3) | 0.011 (1) | |
C1G | 0.08635 (9) | 0.16721 (7) | −0.16566 (4) | 0.011 (1) | |
C1E1 | 0.25135 (9) | −0.04652 (7) | −0.17721 (4) | 0.013 (1) | |
C1D1 | 0.20376 (9) | 0.08535 (7) | −0.20273 (3) | 0.013 (1) | |
C1Z | 0.18290 (9) | −0.09706 (7) | −0.11268 (4) | 0.013 (1) | |
C1D2 | 0.01886 (9) | 0.11386 (7) | −0.10092 (4) | 0.013 (1) | |
C1E2 | 0.06705 (9) | −0.01667 (8) | −0.07405 (4) | 0.013 (1) | |
H1A | 0.07006 | 0.52955 | −0.17707 | 0.014 (4) | |
H1B1 | 0.04423 | 0.31095 | −0.25288 | 0.016 (4) | |
H1B2 | −0.09621 | 0.32677 | −0.17925 | 0.016 (4) | |
H2A1 | 0.09148 | 0.31784 | 0.04781 | 0.016 (4) | |
H2A2 | −0.09968 | 0.40770 | 0.05397 | 0.016 (4) | |
H3A1 | 0.30966 | 0.71877 | 0.13672 | 0.018 (4) | |
H3A2 | 0.34161 | 0.79795 | 0.04932 | 0.018 (4) | |
HN11 | 0.38315 | 0.51581 | −0.17837 | 0.016 (4) | |
HN12 | 0.37513 | 0.34997 | −0.18861 | 0.016 (4) | |
HN13 | 0.29803 | 0.44493 | −0.25472 | 0.016 (4) | |
HN2 | −0.08852 | 0.46827 | −0.06568 | 0.016 (4) | |
HN3 | 0.13114 | 0.66368 | −0.00231 | 0.016 (4) | |
H1D1 | 0.25965 | 0.12356 | −0.25196 | 0.017 (4) | |
H1E1 | 0.34288 | −0.10783 | −0.20536 | 0.017 (4) | |
H1D2 | −0.06714 | 0.17524 | −0.06934 | 0.017 (4) | |
H1E2 | 0.02153 | −0.05945 | −0.02374 | 0.017 (4) | |
HO5 | 0.32902 | −0.26132 | −0.10473 | 0.015 (4) | |
HW1 | 0.12995 | 0.15704 | 0.15916 | 0.021 (5) | |
HW2 | 0.10614 | 0.31906 | 0.17356 | 0.021 (5) |
Geometric parameters (Å, º) top
N1—C1A | 1.4851 (9) | C2A—C2 | 1.5233 (9) |
C1A—C1B | 1.5409 (9) | C2—O2 | 1.2416 (8) |
C1B—C1G | 1.5115 (10) | C2—N3 | 1.3322 (9) |
C1G—C1D1 | 1.3967 (10) | N3—C3A | 1.4436 (9) |
C1G—C1D2 | 1.4002 (9) | C3A—C3 | 1.5307 (10) |
C1D1—C1E1 | 1.3945 (10) | C3—O31 | 1.2539 (9) |
C1D2—C1E2 | 1.3929 (10) | C3—O32 | 1.2603 (9) |
C1E1—C1Z | 1.3904 (10) | O6—HW1 | 0.9640 (5) |
C1E2—C1Z | 1.3949 (10) | O6—HW2 | 0.9632 (5) |
C1Z—OH1 | 1.3701 (9) | OH1—HO5 | 0.9633 (6) |
C1A—C1 | 1.5280 (9) | N1—HN11 | 1.0334 (6) |
C1—O1 | 1.2225 (9) | N1—HN12 | 1.0324 (6) |
C1—N2 | 1.3491 (9) | N1—HN13 | 1.0300 (6) |
N2—C2A | 1.4492 (8) | ||
N1—C1A—C1 | 107.41 (5) | C3A—C3—O32 | 117.97 (6) |
N1—C1A—C1B | 111.30 (6) | O31—C3—O32 | 125.88 (7) |
C1A—C1—O1 | 121.33 (6) | C1A—C1B—C1G | 114.77 (6) |
C1A—C1—N2 | 115.17 (6) | C1B—C1G—C1D1 | 121.49 (6) |
O1—C1—N2 | 123.48 (6) | C1B—C1G—C1D2 | 120.57 (6) |
C1—N2—C2A | 119.06 (6) | C1G—C1D1—C1E1 | 121.54 (6) |
C1—C1A—C1B | 110.91 (6) | C1G—C1D2—C1E2 | 121.25 (7) |
N2—C2A—C2 | 115.05 (6) | C1D1—C1E1—C1Z | 119.44 (7) |
C2A—C2—O2 | 119.58 (6) | C1D2—C1E2—C1Z | 119.62 (7) |
C2A—C2—N3 | 116.95 (6) | C1E1—C1Z—C1E2 | 120.20 (7) |
O2—C2—N3 | 123.46 (7) | C1E1—C1Z—OH1 | 121.63 (6) |
C2—N3—C3A | 124.02 (6) | C1E2—C1Z—OH1 | 118.16 (6) |
N3—C3A—C3 | 115.02 (6) | HW1—O6—HW2 | 110.00 (5) |
C3A—C3—O31 | 116.05 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | H···A | D···A | D—H···A |
O6—HW2···O2 | 1.79 | 2.7525 (7) | 176 |
N1—HN13···O2i | 1.92 | 2.9057 (7) | 159 |
N2—HN2···O31ii | 1.84 | 2.8652 (8) | 174 |
O6—HW1···O31iii | 1.85 | 2.8000 (7) | 167 |
OH1—HO5···O32iv | 1.70 | 2.6547 (9) | 168 |
N1—HN11···O32v | 1.72 | 2.7453 (9) | 172 |
N3—HN3···OH1vi | 2.00 | 2.8534 (8) | 139 |
N1—HN12···O6iv | 1.77 | 2.6898 (9) | 146 |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x−1/2, −y+3/2, −z; (iii) x, y−1, 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 = 212 | V = 1003.3 (4) Å3 |
Orthorhombic, P212121 | Z = 4 |
a = 9.659 (1) Å | Dx = 1.40 Mg m−3 |
b = 9.672 (1) Å | Mo Kα radiation, λ = 0.7107 Å |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O21 | −0.78621 (4) | −0.27464 (4) | −0.22757 (4) | 0.015 (1) | |
O22 | −0.94748 (4) | −0.14220 (4) | −0.31605 (4) | 0.017 (1) | |
C2 | −0.82426 (5) | −0.16995 (5) | −0.28803 (5) | 0.012 (1) | |
C2A | −0.71303 (5) | −0.06645 (5) | −0.32942 (5) | 0.013 (1) | |
N2 | −0.57674 (4) | −0.11497 (4) | −0.29271 (5) | 0.014 (1) | |
C1 | −0.48454 (5) | −0.03277 (5) | −0.23657 (4) | 0.012 (1) | |
O1 | −0.50751 (4) | 0.08792 (4) | −0.20603 (4) | 0.018 (1) | |
C1A | −0.34498 (5) | −0.10086 (5) | −0.21273 (5) | 0.015 (1) | |
N1 | −0.26556 (5) | −0.01730 (5) | −0.12333 (5) | 0.015 (1) | |
C2B | −0.71587 (6) | −0.03553 (5) | −0.46976 (5) | 0.016 (1) | |
C2G | −0.67069 (5) | −0.16118 (5) | −0.54215 (5) | 0.014 (1) | |
O2D1 | −0.71240 (5) | −0.27664 (4) | −0.51789 (4) | 0.019 (1) | |
O2D2 | −0.58222 (5) | −0.13440 (4) | −0.63233 (5) | 0.022 (1) | |
OW1 | −0.95007 (4) | −0.41590 (4) | −0.06995 (4) | 0.018 (1) | |
OW2 | −0.39866 (5) | 0.19248 (5) | −0.48429 (5) | 0.024 (1) | |
H2A | −0.74147 (3) | 0.02974 (3) | −0.28281 (3) | 0.016 (6) | |
HN2 | −0.54291 (3) | −0.21517 (3) | −0.30427 (3) | 0.019 (6) | |
H1A1 | −0.36615 (3) | −0.20362 (3) | −0.17549 (3) | 0.020 (6) | |
H1A2 | −0.29585 (3) | −0.10799 (3) | −0.30204 (3) | 0.020 (7) | |
HN11 | −0.32591 (3) | −0.00694 (3) | −0.04364 (3) | 0.020 (7) | |
HN12 | −0.17890 (3) | −0.07177 (3) | −0.09329 (3) | 0.020 (6) | |
HN13 | −0.24809 (3) | 0.07590 (3) | −0.16559 (3) | 0.020 (6) | |
H2B1 | −0.82348 (3) | −0.02143 (3) | −0.49598 (3) | 0.021 (7) | |
H2B2 | −0.64005 (3) | 0.04544 (3) | −0.48652 (3) | 0.021 (6) | |
HD22 | −0.54140 (4) | −0.21932 (4) | −0.66273 (3) | 0.030 (8) | |
HW11 | −0.89563 (3) | −0.36954 (3) | −0.13191 (3) | 0.024 (7) | |
HW12 | −1.00414 (3) | −0.48600 (3) | −0.11074 (3) | 0.024 (7) | |
HW21 | −0.34677 (4) | 0.21581 (3) | −0.41107 (3) | 0.031 (8) | |
HW22 | −0.44338 (3) | 0.27255 (4) | −0.51934 (3) | 0.031 (8) |
Geometric parameters (Å, º) top
N1—C1A | 1.4705 (7) | C2B—C2G | 1.5069 (7) |
C1A—C1 | 1.5219 (7) | C2G—O2D1 | 1.2159 (6) |
C1—O1 | 1.2327 (6) | C2G—O2D2 | 1.3168 (7) |
C1—N2 | 1.3373 (7) | O2D2—HD22 | 0.9604 (4) |
N2—C2A | 1.4520 (7) | OW1—HW11 | 0.9647 (4) |
C2A—C2 | 1.5346 (7) | OW1—HW12 | 0.9612 (4) |
C2—O21 | 1.2576 (6) | OW2—HW21 | 0.9625 (5) |
C2—O22 | 1.2567 (6) | OW2—HW22 | 0.9713 (5) |
C2A—C2B | 1.5367 (7) | ||
N1—C1A—C1 | 109.53 (4) | O21—C2—O22 | 124.91 (5) |
C1A—C1—O1 | 121.61 (5) | C2A—C2B—C2G | 110.12 (4) |
C1A—C1—N2 | 114.13 (4) | C2B—C2G—O2D1 | 122.27 (5) |
O1—C1—N2 | 124.26 (5) | C2B—C2G—O2D2 | 114.15 (4) |
C1—N2—C2A | 122.25 (4) | O2D1—C2G—O2D2 | 123.58 (5) |
N2—C2A—C2 | 110.17 (4) | C2G—O2D2—HD22 | 110.11 (4) |
N2—C2A—C2B | 110.23 (4) | HW11—OW1—HW12 | 108.10 (4) |
C2A—C2—O21 | 118.07 (4) | HW21—OW2—HW22 | 111.43 (5) |
C2A—C2—O22 | 117.02 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | H···A | D···A | D—H···A |
OW1—HW11···O21 | 1.73 | 2.6905 (6) | 172 |
N1—HN13···O21i | 1.86 | 2.8852 (7) | 170 |
OD22—HD22···O22ii | 1.64 | 2.5826 (6) | 167 |
OW1—HW12···O22iii | 1.77 | 2.6960 (6) | 162 |
N2—HN2···O1iv | 1.97 | 2.9875 (6) | 167 |
OW2—HW22···OW1v | 1.81 | 2.7666 (7) | 172 |
N1—HN11···OW1vi | 1.87 | 2.8110 (7) | 150 |
N1—HN12···OW2vii | 1.83 | 2.7595 (7) | 147 |
OW2—HW21···O21i | 1.96 | 2.9100 (7) | 166 |
Symmetry codes: (i) −x−1, y+1/2, −z−1/2; (ii) x+1/2, −y−1/2, −z−1; (iii) −x+2, y−1/2, −z−1/2; (iv) −x−1, y−1/2, −z−1/2; (v) −x+5/2, −y, z−1/2; (vi) x+1/2, −y−1/2, −z; (vii) −x−1/2, −y, z+1/2. |