Crystals of maleates of three amino acids with hydrophobic side chains [
L-leucenium hydrogen maleate, C
6H
14NO
2+·C
4H
3O
4-, (I),
L-isoleucenium hydrogen maleate hemihydrate, C
6H
14NO
2+·C
4H
3O
4-·0.5H
2O, (II), and
L-norvalinium hydrogen maleate-
L-norvaline (1/1), C
5H
11NO
2+·C
4H
3O
4-·C
5H
12NO
2, (III)], were obtained. The new structures contain
C22(12) chains, or variants thereof, that are a common feature in the crystal structures of amino acid maleates. The
L-leucenium salt is remarkable due to a large number of symmetrically non-equivalent units (
Z' = 3). The
L-isoleucenium salt is a hydrate despite the fact that
L-isoleucine is a nonpolar hydrophobic amino acid (previously known amino acid maleates formed hydrates only with lysine and histidine, which are polar and hydrophilic). The
L-norvalinium salt provides the first example where the dimeric cation
L-Nva
L-NvaH
+ was observed. All three compounds have layered noncentrosymmetric structures. Preliminary tests have shown the presence of the second harmonic generation (SGH) effect for all three compounds.
Supporting information
CCDC references: 1405139; 1405138; 1405137
For all compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for (I); SHELXS97 (Sheldrick, 2008) for (II), (III). For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).
(I)
L-Leucinium hydrogen maleate
top
Crystal data top
C6H14NO2+·C4H3O4− | F(000) = 1584 |
Mr = 247.24 | Dx = 1.265 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 21.7231 (19) Å | Cell parameters from 1466 reflections |
b = 5.6603 (4) Å | θ = 1.9–18.4° |
c = 32.075 (3) Å | µ = 0.11 mm−1 |
β = 98.950 (8)° | T = 298 K |
V = 3895.8 (6) Å3 | Needle, clear light colourless |
Z = 12 | 2.5 × 0.05 × 0.05 mm |
Data collection top
Agilent Xcalibur Gemini Ultra diffractometer with a Ruby detector | 7940 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2843 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.182 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.9° |
ω scans | h = −26→26 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −7→7 |
Tmin = 0.345, Tmax = 1.000 | l = −40→40 |
24642 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.087 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0204P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
7940 reflections | Δρmax = 0.17 e Å−3 |
474 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | |
Special details top
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 | Uiso*/Ueq | |
O51 | 0.5051 (3) | 0.7078 (12) | 0.2477 (2) | 0.071 (2) | |
O21 | 0.7040 (3) | 0.5468 (12) | 0.50318 (18) | 0.0555 (19) | |
O31 | 0.6155 (3) | 0.5850 (13) | 0.4185 (2) | 0.071 (2) | |
O42 | 0.2768 (3) | 0.5282 (12) | 0.64712 (19) | 0.057 (2) | |
O61 | 0.5348 (4) | 0.4129 (12) | 0.29051 (19) | 0.065 (2) | |
H61 | 0.5541 | 0.3933 | 0.3143 | 0.098* | |
O52 | 0.3502 (3) | 0.3342 (12) | 0.7754 (2) | 0.076 (2) | |
O22 | 0.5068 (3) | 0.4577 (13) | 0.8488 (2) | 0.063 (2) | |
N2 | 0.5063 (3) | 0.1572 (12) | 0.7876 (2) | 0.049 (2) | |
H2A | 0.4888 | 0.2650 | 0.7693 | 0.058* | |
H2B | 0.4825 | 0.1353 | 0.8075 | 0.058* | |
H2C | 0.5100 | 0.0216 | 0.7741 | 0.058* | |
O12 | 0.6052 (3) | 0.5617 (14) | 0.8508 (3) | 0.081 (2) | |
H12 | 0.5952 | 0.6808 | 0.8627 | 0.121* | |
O53 | 0.4151 (3) | 0.1556 (12) | −0.0645 (2) | 0.072 (2) | |
O33 | 0.4157 (3) | −0.0606 (12) | 0.1078 (2) | 0.069 (2) | |
O62 | 0.3225 (4) | 0.5702 (12) | 0.7217 (2) | 0.068 (2) | |
H62 | 0.3162 | 0.5620 | 0.6959 | 0.102* | |
O63 | 0.4258 (4) | −0.1558 (13) | −0.0239 (2) | 0.090 (3) | |
H63 | 0.4294 | −0.1867 | 0.0014 | 0.135* | |
N3 | 0.9173 (3) | 0.1039 (13) | 0.8968 (2) | 0.051 (2) | |
H3A | 0.9502 | 0.1159 | 0.8835 | 0.062* | |
H3B | 0.9139 | −0.0443 | 0.9055 | 0.062* | |
H3C | 0.9222 | 0.2002 | 0.9190 | 0.062* | |
O13 | 0.8285 (3) | 0.4576 (15) | 0.8165 (2) | 0.081 (2) | |
H13 | 0.8357 | 0.5912 | 0.8087 | 0.121* | |
O32 | 0.2522 (3) | 0.2399 (12) | 0.6017 (2) | 0.075 (2) | |
O11 | 0.6421 (4) | 0.2531 (13) | 0.4744 (2) | 0.075 (2) | |
H11 | 0.6369 | 0.3393 | 0.4536 | 0.112* | |
O41 | 0.5815 (3) | 0.3584 (11) | 0.3639 (2) | 0.0547 (19) | |
O23 | 0.9291 (3) | 0.4450 (13) | 0.8418 (2) | 0.070 (2) | |
O43 | 0.4309 (5) | −0.2469 (13) | 0.0512 (2) | 0.100 (3) | |
C92 | 0.3095 (5) | 0.1521 (19) | 0.7125 (3) | 0.064 (3) | |
H92 | 0.3153 | 0.0118 | 0.7277 | 0.077* | |
C21 | 0.6919 (4) | 0.1973 (18) | 0.5438 (3) | 0.048 (3) | |
H21 | 0.6935 | 0.0313 | 0.5354 | 0.057* | |
C102 | 0.3278 (5) | 0.3648 (19) | 0.7371 (3) | 0.054 (3) | |
C91 | 0.5486 (5) | 0.8120 (18) | 0.3168 (3) | 0.071 (4) | |
H91 | 0.5427 | 0.9690 | 0.3087 | 0.085* | |
N1 | 0.7531 (3) | 0.2711 (14) | 0.5680 (2) | 0.055 (2) | |
H1A | 0.7826 | 0.2542 | 0.5518 | 0.066* | |
H1B | 0.7621 | 0.1815 | 0.5909 | 0.066* | |
H1C | 0.7511 | 0.4218 | 0.5756 | 0.066* | |
C71 | 0.5914 (5) | 0.561 (2) | 0.3807 (3) | 0.054 (3) | |
C101 | 0.5279 (5) | 0.6353 (18) | 0.2831 (3) | 0.054 (3) | |
C93 | 0.4223 (4) | 0.2234 (18) | 0.0083 (3) | 0.059 (3) | |
H93 | 0.4226 | 0.3840 | 0.0022 | 0.071* | |
C12 | 0.5557 (5) | 0.4345 (19) | 0.8382 (3) | 0.047 (3) | |
C22 | 0.5687 (4) | 0.2397 (18) | 0.8072 (3) | 0.047 (3) | |
H22 | 0.5896 | 0.1088 | 0.8238 | 0.056* | |
C83 | 0.4239 (5) | 0.1712 (17) | 0.0492 (3) | 0.061 (3) | |
H83 | 0.4265 | 0.3011 | 0.0671 | 0.073* | |
C73 | 0.4223 (5) | −0.0584 (19) | 0.0700 (4) | 0.059 (3) | |
C72 | 0.2706 (5) | 0.311 (2) | 0.6383 (3) | 0.052 (3) | |
C81 | 0.5743 (5) | 0.7793 (18) | 0.3569 (3) | 0.064 (3) | |
H81 | 0.5828 | 0.9176 | 0.3724 | 0.077* | |
C103 | 0.4200 (5) | 0.066 (2) | −0.0291 (4) | 0.058 (3) | |
C13 | 0.8784 (5) | 0.3744 (19) | 0.8413 (3) | 0.053 (3) | |
C82 | 0.2857 (5) | 0.1262 (18) | 0.6718 (3) | 0.069 (3) | |
H82 | 0.2773 | −0.0286 | 0.6629 | 0.083* | |
C11 | 0.6809 (5) | 0.356 (2) | 0.5051 (3) | 0.049 (3) | |
C32 | 0.6093 (4) | 0.3118 (17) | 0.7742 (3) | 0.055 (3) | |
H32A | 0.5878 | 0.4366 | 0.7569 | 0.066* | |
H32B | 0.6478 | 0.3778 | 0.7888 | 0.066* | |
C43 | 0.7845 (5) | 0.041 (3) | 0.9172 (4) | 0.088 (4) | |
H43 | 0.8207 | −0.0330 | 0.9342 | 0.106* | |
C41 | 0.5781 (5) | 0.139 (2) | 0.5547 (4) | 0.082 (4) | |
H41 | 0.5648 | 0.2154 | 0.5273 | 0.099* | |
C23 | 0.8597 (4) | 0.1708 (18) | 0.8674 (3) | 0.051 (3) | |
H23 | 0.8461 | 0.0371 | 0.8489 | 0.061* | |
C61 | 0.5320 (5) | 0.213 (3) | 0.5829 (4) | 0.143 (7) | |
H61A | 0.5484 | 0.1757 | 0.6116 | 0.215* | |
H61B | 0.4934 | 0.1310 | 0.5747 | 0.215* | |
H61C | 0.5250 | 0.3805 | 0.5802 | 0.215* | |
C63 | 0.7483 (6) | −0.144 (2) | 0.8922 (5) | 0.141 (7) | |
H63A | 0.7134 | −0.0742 | 0.8745 | 0.211* | |
H63B | 0.7336 | −0.2563 | 0.9108 | 0.211* | |
H63C | 0.7744 | −0.2233 | 0.8750 | 0.211* | |
C33 | 0.8077 (4) | 0.2381 (18) | 0.8920 (3) | 0.053 (3) | |
H33A | 0.8224 | 0.3658 | 0.9112 | 0.063* | |
H33B | 0.7728 | 0.2981 | 0.8723 | 0.063* | |
C31 | 0.6415 (5) | 0.2331 (19) | 0.5711 (3) | 0.064 (3) | |
H31A | 0.6555 | 0.1605 | 0.5983 | 0.077* | |
H31B | 0.6378 | 0.4013 | 0.5758 | 0.077* | |
C51 | 0.5769 (6) | −0.123 (2) | 0.5466 (5) | 0.148 (7) | |
H51A | 0.5928 | −0.2043 | 0.5723 | 0.223* | |
H51B | 0.6022 | −0.1584 | 0.5255 | 0.223* | |
H51C | 0.5348 | −0.1721 | 0.5370 | 0.223* | |
C53 | 0.7445 (6) | 0.158 (3) | 0.9478 (4) | 0.141 (7) | |
H53A | 0.7109 | 0.2450 | 0.9319 | 0.211* | |
H53B | 0.7701 | 0.2629 | 0.9666 | 0.211* | |
H53C | 0.7278 | 0.0372 | 0.9639 | 0.211* | |
C62 | 0.6695 (6) | −0.060 (2) | 0.7675 (5) | 0.132 (6) | |
H62A | 0.7080 | 0.0166 | 0.7787 | 0.199* | |
H62B | 0.6772 | −0.1808 | 0.7480 | 0.199* | |
H62C | 0.6515 | −0.1287 | 0.7902 | 0.199* | |
C42 | 0.6254 (5) | 0.119 (2) | 0.7451 (4) | 0.082 (4) | |
H42 | 0.5869 | 0.0374 | 0.7330 | 0.099* | |
C52 | 0.6536 (6) | 0.236 (3) | 0.7093 (4) | 0.132 (6) | |
H52A | 0.6273 | 0.3640 | 0.6978 | 0.197* | |
H52B | 0.6566 | 0.1217 | 0.6876 | 0.197* | |
H52C | 0.6943 | 0.2952 | 0.7201 | 0.197* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O51 | 0.100 (6) | 0.074 (5) | 0.033 (5) | 0.007 (5) | −0.011 (4) | 0.011 (4) |
O21 | 0.087 (5) | 0.052 (4) | 0.025 (4) | −0.020 (4) | 0.003 (4) | 0.012 (4) |
O31 | 0.089 (5) | 0.083 (6) | 0.031 (4) | 0.000 (5) | −0.021 (4) | 0.005 (4) |
O42 | 0.095 (5) | 0.045 (5) | 0.028 (4) | 0.012 (4) | −0.002 (4) | 0.004 (4) |
O61 | 0.105 (6) | 0.056 (5) | 0.024 (4) | 0.001 (5) | −0.024 (4) | −0.006 (4) |
O52 | 0.116 (6) | 0.069 (5) | 0.034 (5) | −0.006 (5) | −0.011 (4) | 0.004 (4) |
O22 | 0.067 (5) | 0.087 (5) | 0.037 (4) | −0.003 (5) | 0.017 (4) | −0.016 (4) |
N2 | 0.065 (6) | 0.058 (5) | 0.025 (5) | −0.003 (5) | 0.011 (4) | −0.005 (4) |
O12 | 0.093 (6) | 0.096 (7) | 0.058 (6) | −0.022 (6) | 0.025 (5) | −0.031 (5) |
O53 | 0.106 (6) | 0.085 (6) | 0.024 (4) | −0.004 (5) | 0.004 (4) | 0.009 (4) |
O33 | 0.112 (6) | 0.070 (5) | 0.027 (4) | 0.007 (5) | 0.013 (4) | 0.006 (4) |
O62 | 0.120 (7) | 0.050 (5) | 0.030 (4) | −0.004 (5) | −0.002 (5) | 0.001 (4) |
O63 | 0.178 (9) | 0.066 (6) | 0.024 (5) | 0.011 (6) | 0.005 (5) | −0.007 (4) |
N3 | 0.065 (5) | 0.061 (6) | 0.031 (5) | −0.002 (5) | 0.014 (4) | 0.001 (4) |
O13 | 0.093 (6) | 0.100 (7) | 0.046 (5) | −0.004 (6) | 0.003 (4) | 0.031 (5) |
O32 | 0.124 (7) | 0.062 (5) | 0.029 (5) | −0.004 (5) | −0.016 (4) | −0.002 (4) |
O11 | 0.101 (6) | 0.083 (6) | 0.028 (5) | −0.028 (5) | −0.025 (4) | 0.014 (4) |
O41 | 0.076 (5) | 0.039 (4) | 0.043 (5) | −0.012 (4) | −0.008 (4) | 0.007 (4) |
O23 | 0.071 (5) | 0.083 (6) | 0.055 (5) | −0.023 (5) | 0.008 (4) | 0.017 (5) |
O43 | 0.215 (10) | 0.049 (5) | 0.040 (5) | 0.020 (6) | 0.032 (6) | 0.011 (4) |
C92 | 0.102 (9) | 0.054 (8) | 0.034 (7) | 0.000 (7) | 0.004 (6) | 0.012 (6) |
C21 | 0.059 (7) | 0.056 (7) | 0.028 (6) | −0.001 (6) | 0.005 (5) | −0.005 (5) |
C102 | 0.077 (8) | 0.046 (7) | 0.037 (7) | 0.002 (6) | 0.002 (6) | −0.010 (6) |
C91 | 0.111 (10) | 0.049 (7) | 0.044 (8) | 0.005 (7) | −0.015 (7) | −0.009 (6) |
N1 | 0.067 (6) | 0.077 (6) | 0.019 (5) | 0.014 (5) | −0.002 (4) | 0.014 (4) |
C71 | 0.055 (7) | 0.057 (8) | 0.046 (8) | −0.005 (7) | −0.004 (6) | 0.015 (7) |
C101 | 0.080 (8) | 0.047 (7) | 0.034 (7) | 0.005 (6) | 0.006 (6) | 0.002 (6) |
C93 | 0.093 (8) | 0.047 (6) | 0.034 (7) | −0.001 (6) | 0.002 (6) | 0.001 (6) |
C12 | 0.067 (8) | 0.053 (7) | 0.022 (6) | 0.000 (7) | 0.008 (6) | −0.003 (5) |
C22 | 0.042 (6) | 0.064 (7) | 0.031 (6) | 0.005 (6) | −0.005 (5) | −0.008 (6) |
C83 | 0.086 (8) | 0.043 (7) | 0.049 (8) | 0.001 (6) | 0.001 (6) | −0.015 (6) |
C73 | 0.087 (8) | 0.035 (6) | 0.057 (8) | 0.025 (7) | 0.014 (7) | 0.007 (7) |
C72 | 0.062 (7) | 0.061 (8) | 0.030 (7) | 0.003 (7) | 0.001 (5) | 0.009 (6) |
C81 | 0.101 (9) | 0.049 (7) | 0.038 (7) | −0.004 (7) | −0.007 (6) | −0.005 (6) |
C103 | 0.063 (7) | 0.058 (8) | 0.049 (8) | 0.010 (7) | −0.001 (6) | −0.008 (7) |
C13 | 0.077 (8) | 0.061 (8) | 0.019 (6) | −0.006 (7) | 0.002 (6) | 0.005 (5) |
C82 | 0.107 (9) | 0.051 (8) | 0.042 (8) | −0.008 (7) | −0.006 (7) | −0.004 (6) |
C11 | 0.053 (7) | 0.071 (8) | 0.023 (6) | −0.003 (6) | 0.005 (5) | 0.011 (6) |
C32 | 0.061 (7) | 0.078 (8) | 0.029 (6) | −0.006 (6) | 0.017 (5) | 0.005 (6) |
C43 | 0.055 (8) | 0.113 (12) | 0.097 (11) | 0.014 (8) | 0.012 (8) | 0.036 (10) |
C41 | 0.053 (8) | 0.122 (12) | 0.075 (10) | 0.006 (8) | 0.020 (7) | 0.029 (8) |
C23 | 0.066 (7) | 0.066 (7) | 0.019 (6) | 0.005 (6) | −0.002 (5) | 0.000 (5) |
C61 | 0.087 (10) | 0.240 (19) | 0.116 (14) | 0.027 (11) | 0.055 (10) | 0.022 (13) |
C63 | 0.137 (14) | 0.090 (11) | 0.21 (2) | −0.046 (11) | 0.080 (13) | −0.025 (12) |
C33 | 0.057 (7) | 0.066 (7) | 0.036 (6) | −0.004 (6) | 0.008 (5) | −0.001 (6) |
C31 | 0.078 (8) | 0.083 (8) | 0.036 (7) | 0.008 (7) | 0.020 (6) | 0.004 (6) |
C51 | 0.108 (12) | 0.094 (13) | 0.24 (2) | −0.020 (10) | 0.026 (12) | −0.022 (13) |
C53 | 0.117 (12) | 0.219 (19) | 0.102 (13) | −0.013 (12) | 0.066 (10) | 0.013 (13) |
C62 | 0.169 (15) | 0.093 (11) | 0.162 (16) | 0.031 (12) | 0.108 (13) | 0.009 (12) |
C42 | 0.075 (9) | 0.113 (11) | 0.068 (9) | −0.016 (8) | 0.039 (7) | −0.030 (8) |
C52 | 0.138 (12) | 0.214 (17) | 0.056 (10) | 0.011 (12) | 0.059 (9) | −0.013 (11) |
Geometric parameters (Å, º) top
O51—C101 | 1.234 (11) | C93—C103 | 1.489 (13) |
O21—C11 | 1.199 (10) | C12—C22 | 1.540 (12) |
O31—C71 | 1.251 (11) | C22—H22 | 0.9800 |
O42—C72 | 1.262 (11) | C22—C32 | 1.536 (11) |
O61—H61 | 0.8200 | C83—H83 | 0.9300 |
O61—C101 | 1.286 (10) | C83—C73 | 1.465 (13) |
O52—C102 | 1.262 (11) | C72—C82 | 1.499 (13) |
O22—C12 | 1.172 (10) | C81—H81 | 0.9300 |
N2—H2A | 0.8900 | C13—C23 | 1.518 (13) |
N2—H2B | 0.8900 | C82—H82 | 0.9300 |
N2—H2C | 0.8900 | C32—H32A | 0.9700 |
N2—C22 | 1.480 (10) | C32—H32B | 0.9700 |
O12—H12 | 0.8200 | C32—C42 | 1.513 (13) |
O12—C12 | 1.305 (10) | C43—H43 | 0.9800 |
O53—C103 | 1.233 (12) | C43—C63 | 1.473 (16) |
O33—C73 | 1.244 (11) | C43—C33 | 1.507 (14) |
O62—H62 | 0.8200 | C43—C53 | 1.556 (15) |
O62—C102 | 1.261 (11) | C41—H41 | 0.9800 |
O63—H63 | 0.8200 | C41—C61 | 1.509 (15) |
O63—C103 | 1.269 (11) | C41—C31 | 1.494 (13) |
N3—H3A | 0.8900 | C41—C51 | 1.504 (16) |
N3—H3B | 0.8900 | C23—H23 | 0.9800 |
N3—H3C | 0.8900 | C23—C33 | 1.523 (11) |
N3—C23 | 1.494 (10) | C61—H61A | 0.9600 |
O13—H13 | 0.8200 | C61—H61B | 0.9600 |
O13—C13 | 1.327 (11) | C61—H61C | 0.9600 |
O32—C72 | 1.247 (11) | C63—H63A | 0.9600 |
O11—H11 | 0.8200 | C63—H63B | 0.9600 |
O11—C11 | 1.325 (11) | C63—H63C | 0.9600 |
O41—C71 | 1.271 (12) | C33—H33A | 0.9700 |
O23—C13 | 1.170 (10) | C33—H33B | 0.9700 |
O43—C73 | 1.254 (11) | C31—H31A | 0.9700 |
C92—H92 | 0.9300 | C31—H31B | 0.9700 |
C92—C102 | 1.459 (13) | C51—H51A | 0.9600 |
C92—C82 | 1.337 (13) | C51—H51B | 0.9600 |
C21—H21 | 0.9800 | C51—H51C | 0.9600 |
C21—N1 | 1.490 (10) | C53—H53A | 0.9600 |
C21—C11 | 1.521 (12) | C53—H53B | 0.9600 |
C21—C31 | 1.517 (11) | C53—H53C | 0.9600 |
C91—H91 | 0.9300 | C62—H62A | 0.9600 |
C91—C101 | 1.491 (13) | C62—H62B | 0.9600 |
C91—C81 | 1.332 (13) | C62—H62C | 0.9600 |
N1—H1A | 0.8900 | C62—C42 | 1.494 (16) |
N1—H1B | 0.8900 | C42—H42 | 0.9800 |
N1—H1C | 0.8900 | C42—C52 | 1.535 (15) |
C71—C81 | 1.470 (13) | C52—H52A | 0.9600 |
C93—H93 | 0.9300 | C52—H52B | 0.9600 |
C93—C83 | 1.339 (12) | C52—H52C | 0.9600 |
| | | |
C101—O61—H61 | 109.5 | O11—C11—C21 | 110.5 (9) |
H2A—N2—H2B | 109.5 | C22—C32—H32A | 108.2 |
H2A—N2—H2C | 109.5 | C22—C32—H32B | 108.2 |
H2B—N2—H2C | 109.5 | H32A—C32—H32B | 107.3 |
C22—N2—H2A | 109.5 | C42—C32—C22 | 116.5 (8) |
C22—N2—H2B | 109.5 | C42—C32—H32A | 108.2 |
C22—N2—H2C | 109.5 | C42—C32—H32B | 108.2 |
C12—O12—H12 | 109.5 | C63—C43—H43 | 108.1 |
C102—O62—H62 | 109.5 | C63—C43—C33 | 115.5 (12) |
C103—O63—H63 | 109.5 | C63—C43—C53 | 110.0 (11) |
H3A—N3—H3B | 109.5 | C33—C43—H43 | 108.1 |
H3A—N3—H3C | 109.5 | C33—C43—C53 | 107.0 (11) |
H3B—N3—H3C | 109.5 | C53—C43—H43 | 108.1 |
C23—N3—H3A | 109.5 | C61—C41—H41 | 106.6 |
C23—N3—H3B | 109.5 | C31—C41—H41 | 106.6 |
C23—N3—H3C | 109.5 | C31—C41—C61 | 110.6 (11) |
C13—O13—H13 | 109.5 | C31—C41—C51 | 113.6 (11) |
C11—O11—H11 | 109.5 | C51—C41—H41 | 106.6 |
C102—C92—H92 | 114.8 | C51—C41—C61 | 112.4 (12) |
C82—C92—H92 | 114.8 | N3—C23—C13 | 105.7 (8) |
C82—C92—C102 | 130.5 (10) | N3—C23—H23 | 109.3 |
N1—C21—H21 | 110.3 | N3—C23—C33 | 110.7 (7) |
N1—C21—C11 | 105.9 (8) | C13—C23—H23 | 109.3 |
N1—C21—C31 | 109.2 (8) | C13—C23—C33 | 112.4 (8) |
C11—C21—H21 | 110.3 | C33—C23—H23 | 109.3 |
C31—C21—H21 | 110.3 | C41—C61—H61A | 109.5 |
C31—C21—C11 | 110.8 (8) | C41—C61—H61B | 109.5 |
O52—C102—C92 | 116.3 (10) | C41—C61—H61C | 109.5 |
O62—C102—O52 | 120.3 (10) | H61A—C61—H61B | 109.5 |
O62—C102—C92 | 123.3 (10) | H61A—C61—H61C | 109.5 |
C101—C91—H91 | 115.1 | H61B—C61—H61C | 109.5 |
C81—C91—H91 | 115.1 | C43—C63—H63A | 109.5 |
C81—C91—C101 | 129.9 (10) | C43—C63—H63B | 109.5 |
C21—N1—H1A | 109.5 | C43—C63—H63C | 109.5 |
C21—N1—H1B | 109.5 | H63A—C63—H63B | 109.5 |
C21—N1—H1C | 109.5 | H63A—C63—H63C | 109.5 |
H1A—N1—H1B | 109.5 | H63B—C63—H63C | 109.5 |
H1A—N1—H1C | 109.5 | C43—C33—C23 | 115.4 (9) |
H1B—N1—H1C | 109.5 | C43—C33—H33A | 108.4 |
O31—C71—O41 | 121.8 (10) | C43—C33—H33B | 108.4 |
O31—C71—C81 | 116.5 (11) | C23—C33—H33A | 108.4 |
O41—C71—C81 | 121.7 (9) | C23—C33—H33B | 108.4 |
O51—C101—O61 | 120.9 (10) | H33A—C33—H33B | 107.5 |
O51—C101—C91 | 118.5 (10) | C21—C31—H31A | 108.0 |
O61—C101—C91 | 120.6 (10) | C21—C31—H31B | 108.0 |
C83—C93—H93 | 114.8 | C41—C31—C21 | 117.3 (9) |
C83—C93—C103 | 130.4 (10) | C41—C31—H31A | 108.0 |
C103—C93—H93 | 114.8 | C41—C31—H31B | 108.0 |
O22—C12—O12 | 126.1 (10) | H31A—C31—H31B | 107.2 |
O22—C12—C22 | 122.2 (10) | C41—C51—H51A | 109.5 |
O12—C12—C22 | 111.7 (9) | C41—C51—H51B | 109.5 |
N2—C22—C12 | 104.6 (7) | C41—C51—H51C | 109.5 |
N2—C22—H22 | 107.9 | H51A—C51—H51B | 109.5 |
N2—C22—C32 | 112.1 (7) | H51A—C51—H51C | 109.5 |
C12—C22—H22 | 107.9 | H51B—C51—H51C | 109.5 |
C32—C22—C12 | 116.0 (8) | C43—C53—H53A | 109.5 |
C32—C22—H22 | 107.9 | C43—C53—H53B | 109.5 |
C93—C83—H83 | 115.0 | C43—C53—H53C | 109.5 |
C93—C83—C73 | 130.1 (10) | H53A—C53—H53B | 109.5 |
C73—C83—H83 | 115.0 | H53A—C53—H53C | 109.5 |
O33—C73—O43 | 120.6 (10) | H53B—C53—H53C | 109.5 |
O33—C73—C83 | 118.0 (10) | H62A—C62—H62B | 109.5 |
O43—C73—C83 | 121.3 (10) | H62A—C62—H62C | 109.5 |
O42—C72—C82 | 121.1 (10) | H62B—C62—H62C | 109.5 |
O32—C72—O42 | 122.2 (10) | C42—C62—H62A | 109.5 |
O32—C72—C82 | 116.7 (10) | C42—C62—H62B | 109.5 |
C91—C81—C71 | 130.7 (10) | C42—C62—H62C | 109.5 |
C91—C81—H81 | 114.7 | C32—C42—H42 | 108.6 |
C71—C81—H81 | 114.7 | C32—C42—C52 | 107.8 (10) |
O53—C103—O63 | 121.4 (11) | C62—C42—C32 | 112.6 (11) |
O53—C103—C93 | 118.7 (10) | C62—C42—H42 | 108.6 |
O63—C103—C93 | 119.7 (10) | C62—C42—C52 | 110.6 (10) |
O13—C13—C23 | 109.6 (9) | C52—C42—H42 | 108.6 |
O23—C13—O13 | 124.6 (10) | C42—C52—H52A | 109.5 |
O23—C13—C23 | 125.8 (10) | C42—C52—H52B | 109.5 |
C92—C82—C72 | 129.2 (10) | C42—C52—H52C | 109.5 |
C92—C82—H82 | 115.4 | H52A—C52—H52B | 109.5 |
C72—C82—H82 | 115.4 | H52A—C52—H52C | 109.5 |
O21—C11—O11 | 125.5 (9) | H52B—C52—H52C | 109.5 |
O21—C11—C21 | 124.0 (9) | | |
| | | |
O31—C71—C81—C91 | 179.6 (12) | C93—C83—C73—O43 | 13.9 (19) |
O42—C72—C82—C92 | −3.8 (19) | C12—C22—C32—C42 | 176.7 (9) |
O22—C12—C22—N2 | 15.7 (13) | C22—C32—C42—C62 | −69.5 (13) |
O22—C12—C22—C32 | 139.7 (10) | C22—C32—C42—C52 | 168.2 (9) |
N2—C22—C32—C42 | −63.3 (12) | C83—C93—C103—O53 | 175.8 (11) |
O12—C12—C22—N2 | −165.2 (8) | C83—C93—C103—O63 | −7.2 (18) |
O12—C12—C22—C32 | −41.2 (12) | C81—C91—C101—O51 | −180.0 (12) |
N3—C23—C33—C43 | −64.8 (12) | C81—C91—C101—O61 | −1 (2) |
O13—C13—C23—N3 | −175.0 (8) | C103—C93—C83—C73 | −2 (2) |
O13—C13—C23—C33 | −54.2 (11) | C13—C23—C33—C43 | 177.3 (9) |
O32—C72—C82—C92 | 175.6 (11) | C82—C92—C102—O52 | −178.7 (12) |
O41—C71—C81—C91 | −1 (2) | C82—C92—C102—O62 | 1 (2) |
O23—C13—C23—N3 | 6.7 (14) | C11—C21—C31—C41 | 71.7 (12) |
O23—C13—C23—C33 | 127.5 (11) | C61—C41—C31—C21 | −173.5 (10) |
C102—C92—C82—C72 | 0 (2) | C63—C43—C33—C23 | −70.7 (13) |
N1—C21—C11—O21 | −24.2 (13) | C31—C21—C11—O21 | 94.1 (12) |
N1—C21—C11—O11 | 156.4 (8) | C31—C21—C11—O11 | −85.3 (11) |
N1—C21—C31—C41 | −172.0 (9) | C51—C41—C31—C21 | 58.9 (15) |
C101—C91—C81—C71 | 1 (2) | C53—C43—C33—C23 | 166.5 (9) |
C93—C83—C73—O33 | −170.2 (11) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O61—H61···O41 | 0.82 | 1.62 | 2.433 (8) | 171 |
N2—H2B···O23i | 0.89 | 2.03 | 2.860 (9) | 155 |
N2—H2C···O51ii | 0.89 | 1.92 | 2.780 (10) | 162 |
O12—H12···O33iii | 0.82 | 1.78 | 2.592 (10) | 172 |
O62—H62···O42 | 0.82 | 1.67 | 2.454 (9) | 159 |
O63—H63···O43 | 0.82 | 1.63 | 2.449 (10) | 176 |
N3—H3A···O22iv | 0.89 | 1.99 | 2.786 (9) | 148 |
N3—H3B···O53v | 0.89 | 1.95 | 2.829 (10) | 168 |
N3—H3C···O63vi | 0.89 | 2.00 | 2.866 (10) | 165 |
O13—H13···O52vii | 0.82 | 1.80 | 2.589 (10) | 161 |
O11—H11···O31 | 0.82 | 1.80 | 2.599 (9) | 163 |
N1—H1A···O21viii | 0.89 | 2.18 | 2.890 (9) | 137 |
N1—H1B···O42iv | 0.89 | 1.98 | 2.863 (9) | 170 |
N1—H1C···O32vii | 0.89 | 1.99 | 2.867 (10) | 171 |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x+1, y−1, −z+1; (iii) −x+1, y+1, −z+1; (iv) x+1/2, y−1/2, z; (v) x+1/2, y−1/2, z+1; (vi) x+1/2, y+1/2, z+1; (vii) x+1/2, y+1/2, z; (viii) −x+3/2, y−1/2, −z+1. |
(II)
L-Lisinium hydrogen maleate hemihydrate
top
Crystal data top
C6H14NO2+·C4H3O4−·0.5H2O | F(000) = 548 |
Mr = 256.26 | Dx = 1.280 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5217 (9) Å | Cell parameters from 3141 reflections |
b = 5.9974 (3) Å | θ = 1.8–28.1° |
c = 19.3426 (12) Å | µ = 0.11 mm−1 |
β = 95.848 (6)° | T = 298 K |
V = 1329.62 (15) Å3 | Needle, clear light colourless |
Z = 4 | 0.25 × 0.1 × 0.05 mm |
Data collection top
Agilent Xcalibur Gemini Ultra diffractometer with Ruby detector | 5459 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3452 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −7→7 |
Tmin = 0.949, Tmax = 1.000 | l = −24→24 |
17017 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5459 reflections | Δρmax = 0.15 e Å−3 |
329 parameters | Δρmin = −0.14 e Å−3 |
1 restraint | |
Special details top
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 | Uiso*/Ueq | |
O1 | 0.2729 (3) | 0.3576 (6) | 0.55993 (14) | 0.0558 (9) | |
H1 | 0.2965 | 0.2392 | 0.5773 | 0.084* | |
O52 | 0.6863 (3) | 0.4547 (6) | 0.39132 (15) | 0.0615 (10) | |
O2 | 0.2448 (4) | 0.1518 (7) | 0.46452 (18) | 0.0822 (13) | |
O62 | 0.5944 (3) | 0.6140 (6) | 0.29963 (17) | 0.0595 (10) | |
H62 | 0.5543 | 0.5771 | 0.2640 | 0.089* | |
O42 | 0.4728 (3) | 0.4996 (6) | 0.19698 (16) | 0.0658 (11) | |
O32 | 0.4175 (3) | 0.1871 (6) | 0.14387 (14) | 0.0627 (10) | |
N1 | 0.1596 (3) | 0.7067 (6) | 0.50321 (16) | 0.0438 (10) | |
H1A | 0.1215 | 0.8152 | 0.4791 | 0.053* | |
H1B | 0.2227 | 0.7629 | 0.5275 | 0.053* | |
H1C | 0.1133 | 0.6458 | 0.5321 | 0.053* | |
C1 | 0.2393 (4) | 0.3277 (9) | 0.4933 (2) | 0.0469 (12) | |
C2 | 0.1956 (4) | 0.5335 (8) | 0.4547 (2) | 0.0412 (12) | |
H2 | 0.1253 | 0.4901 | 0.4249 | 0.049* | |
C102 | 0.6266 (4) | 0.4406 (9) | 0.3344 (2) | 0.0456 (12) | |
C3 | 0.2810 (4) | 0.6275 (9) | 0.4072 (2) | 0.0544 (14) | |
H3 | 0.2462 | 0.7642 | 0.3865 | 0.065* | |
C92 | 0.5923 (4) | 0.2154 (9) | 0.3099 (2) | 0.0481 (13) | |
H92 | 0.6199 | 0.0997 | 0.3391 | 0.058* | |
C82 | 0.5268 (4) | 0.1513 (9) | 0.2514 (2) | 0.0509 (13) | |
H82 | 0.5163 | −0.0018 | 0.2464 | 0.061* | |
C72 | 0.4687 (4) | 0.2892 (9) | 0.1939 (2) | 0.0481 (13) | |
C4 | 0.3980 (4) | 0.6926 (11) | 0.4465 (3) | 0.0767 (18) | |
H4A | 0.4381 | 0.5607 | 0.4640 | 0.115* | |
H4B | 0.3847 | 0.7888 | 0.4846 | 0.115* | |
H4C | 0.4447 | 0.7690 | 0.4156 | 0.115* | |
C5 | 0.3014 (5) | 0.4712 (12) | 0.3475 (3) | 0.0799 (19) | |
H5A | 0.3526 | 0.5456 | 0.3180 | 0.096* | |
H5B | 0.3423 | 0.3404 | 0.3668 | 0.096* | |
C6 | 0.1947 (6) | 0.3948 (17) | 0.3028 (3) | 0.130 (4) | |
H6A | 0.2174 | 0.3005 | 0.2664 | 0.196* | |
H6B | 0.1535 | 0.5221 | 0.2827 | 0.196* | |
H6C | 0.1450 | 0.3131 | 0.3306 | 0.196* | |
O5 | 0.0101 (3) | 0.4666 (6) | 0.58072 (14) | 0.0604 (10) | |
O6 | 0.0433 (4) | 0.1552 (7) | 0.63896 (16) | 0.0750 (12) | |
H6 | 0.0732 | 0.1147 | 0.6772 | 0.113* | |
O1W1 | 0.4655 (3) | 0.3364 (7) | 0.90954 (13) | 0.0605 (10) | |
H1WA | 0.5088 | 0.4123 | 0.8854 | 0.091* | |
H1WB | 0.4198 | 0.2555 | 0.8828 | 0.091* | |
O3 | 0.2264 (3) | 0.1948 (7) | 0.84460 (15) | 0.0716 (12) | |
O4 | 0.1333 (3) | 0.0388 (6) | 0.75155 (16) | 0.0704 (12) | |
O12 | 0.1953 (3) | 0.8213 (7) | −0.09220 (17) | 0.0786 (12) | |
H12 | 0.2089 | 0.9363 | −0.1129 | 0.118* | |
N2 | 0.3793 (3) | 0.4947 (7) | 0.02938 (17) | 0.0460 (10) | |
H2A | 0.3684 | 0.3905 | 0.0608 | 0.055* | |
H2B | 0.4133 | 0.6131 | 0.0505 | 0.055* | |
H2C | 0.4247 | 0.4409 | −0.0012 | 0.055* | |
O22 | 0.3705 (3) | 0.8829 (8) | −0.03935 (19) | 0.0900 (15) | |
C12 | 0.2850 (4) | 0.7722 (10) | −0.0474 (2) | 0.0507 (13) | |
C7 | 0.1728 (4) | 0.2076 (10) | 0.7847 (2) | 0.0549 (14) | |
C22 | 0.2642 (4) | 0.5613 (9) | −0.0074 (2) | 0.0480 (13) | |
H22 | 0.2400 | 0.4444 | −0.0413 | 0.058* | |
C9 | 0.1072 (4) | 0.4986 (9) | 0.6932 (2) | 0.0532 (14) | |
H9 | 0.1073 | 0.6518 | 0.6858 | 0.064* | |
C32 | 0.1690 (4) | 0.5858 (10) | 0.0408 (3) | 0.0597 (15) | |
H32 | 0.1007 | 0.6476 | 0.0130 | 0.072* | |
C10 | 0.0504 (4) | 0.3657 (10) | 0.6344 (2) | 0.0513 (14) | |
C52 | 0.2014 (5) | 0.7500 (11) | 0.1001 (3) | 0.0708 (16) | |
H52A | 0.2620 | 0.6837 | 0.1321 | 0.085* | |
H52B | 0.2337 | 0.8834 | 0.0810 | 0.085* | |
C8 | 0.1579 (4) | 0.4335 (10) | 0.7550 (2) | 0.0563 (14) | |
H8 | 0.1886 | 0.5480 | 0.7837 | 0.068* | |
C62 | 0.1007 (6) | 0.8169 (14) | 0.1402 (3) | 0.109 (3) | |
H62A | 0.1289 | 0.9108 | 0.1785 | 0.163* | |
H62B | 0.0656 | 0.6857 | 0.1576 | 0.163* | |
H62C | 0.0436 | 0.8966 | 0.1101 | 0.163* | |
C42 | 0.1327 (5) | 0.3614 (10) | 0.0677 (3) | 0.0814 (19) | |
H42A | 0.1956 | 0.3003 | 0.0983 | 0.122* | |
H42B | 0.1143 | 0.2618 | 0.0292 | 0.122* | |
H42C | 0.0654 | 0.3800 | 0.0925 | 0.122* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.074 (2) | 0.038 (2) | 0.0506 (17) | 0.0084 (18) | −0.0163 (16) | 0.0056 (17) |
O52 | 0.077 (2) | 0.050 (3) | 0.0506 (18) | −0.003 (2) | −0.0233 (17) | −0.0063 (19) |
O2 | 0.142 (4) | 0.036 (3) | 0.063 (2) | 0.008 (2) | −0.020 (2) | −0.003 (2) |
O62 | 0.082 (3) | 0.038 (2) | 0.055 (2) | −0.0075 (19) | −0.0090 (19) | −0.0017 (18) |
O42 | 0.107 (3) | 0.041 (3) | 0.046 (2) | 0.013 (2) | −0.0121 (18) | 0.0069 (18) |
O32 | 0.076 (2) | 0.064 (3) | 0.0424 (17) | 0.006 (2) | −0.0201 (17) | −0.0056 (19) |
N1 | 0.045 (2) | 0.037 (3) | 0.048 (2) | 0.0046 (19) | −0.0013 (18) | 0.010 (2) |
C1 | 0.052 (3) | 0.039 (3) | 0.047 (3) | −0.003 (2) | −0.007 (2) | −0.001 (3) |
C2 | 0.046 (3) | 0.035 (3) | 0.041 (2) | 0.003 (2) | −0.004 (2) | −0.003 (2) |
C102 | 0.051 (3) | 0.040 (3) | 0.045 (3) | 0.002 (3) | 0.000 (2) | 0.002 (3) |
C3 | 0.055 (3) | 0.055 (4) | 0.054 (3) | 0.007 (3) | 0.012 (3) | 0.007 (3) |
C92 | 0.062 (3) | 0.037 (3) | 0.043 (3) | 0.005 (3) | −0.010 (2) | 0.001 (2) |
C82 | 0.066 (3) | 0.036 (3) | 0.047 (3) | 0.001 (3) | −0.013 (2) | 0.000 (2) |
C72 | 0.053 (3) | 0.053 (4) | 0.036 (3) | 0.010 (3) | −0.003 (2) | −0.001 (3) |
C4 | 0.056 (4) | 0.077 (5) | 0.100 (4) | −0.010 (3) | 0.020 (3) | −0.002 (4) |
C5 | 0.079 (4) | 0.092 (5) | 0.071 (3) | −0.001 (4) | 0.022 (3) | −0.008 (4) |
C6 | 0.111 (6) | 0.208 (11) | 0.070 (4) | 0.006 (6) | 0.000 (4) | −0.052 (6) |
O5 | 0.060 (2) | 0.076 (3) | 0.0413 (16) | −0.023 (2) | −0.0131 (15) | 0.016 (2) |
O6 | 0.100 (3) | 0.065 (3) | 0.052 (2) | −0.032 (2) | −0.031 (2) | 0.007 (2) |
O1W1 | 0.074 (3) | 0.062 (3) | 0.0430 (16) | −0.009 (2) | −0.0062 (17) | −0.0055 (19) |
O3 | 0.092 (3) | 0.072 (3) | 0.0446 (18) | −0.008 (2) | −0.0236 (18) | 0.013 (2) |
O4 | 0.101 (3) | 0.044 (3) | 0.059 (2) | −0.017 (2) | −0.025 (2) | 0.0058 (19) |
O12 | 0.076 (3) | 0.081 (3) | 0.070 (2) | −0.013 (2) | −0.031 (2) | 0.027 (2) |
N2 | 0.045 (2) | 0.049 (3) | 0.0442 (19) | 0.005 (2) | 0.0015 (17) | 0.004 (2) |
O22 | 0.058 (3) | 0.102 (4) | 0.102 (3) | −0.026 (2) | −0.027 (2) | 0.058 (3) |
C12 | 0.045 (3) | 0.060 (4) | 0.045 (3) | −0.007 (3) | −0.003 (2) | 0.007 (3) |
C7 | 0.059 (3) | 0.059 (4) | 0.044 (3) | −0.007 (3) | −0.005 (2) | 0.008 (3) |
C22 | 0.045 (3) | 0.051 (4) | 0.046 (3) | −0.004 (2) | −0.010 (2) | 0.007 (2) |
C9 | 0.071 (4) | 0.041 (3) | 0.044 (2) | −0.010 (3) | −0.012 (2) | 0.001 (3) |
C32 | 0.041 (3) | 0.066 (4) | 0.071 (3) | 0.001 (3) | 0.000 (3) | 0.024 (3) |
C10 | 0.048 (3) | 0.060 (4) | 0.046 (3) | −0.019 (3) | 0.003 (2) | 0.001 (3) |
C52 | 0.067 (4) | 0.067 (4) | 0.081 (4) | 0.012 (3) | 0.021 (3) | 0.004 (3) |
C8 | 0.072 (4) | 0.048 (3) | 0.046 (3) | −0.014 (3) | −0.012 (2) | −0.002 (3) |
C62 | 0.115 (6) | 0.104 (6) | 0.118 (5) | 0.028 (5) | 0.066 (5) | 0.019 (5) |
C42 | 0.066 (4) | 0.072 (5) | 0.105 (4) | −0.016 (3) | 0.003 (3) | 0.031 (4) |
Geometric parameters (Å, º) top
O1—H1 | 0.8200 | O6—H6 | 0.8200 |
O1—C1 | 1.319 (5) | O6—C10 | 1.269 (6) |
O52—C102 | 1.240 (5) | O1W1—H1WA | 0.8499 |
O2—C1 | 1.198 (6) | O1W1—H1WB | 0.8505 |
O62—H62 | 0.8200 | O3—C7 | 1.257 (5) |
O62—C102 | 1.273 (5) | O4—C7 | 1.259 (6) |
O42—C72 | 1.264 (6) | O12—H12 | 0.8200 |
O32—C72 | 1.242 (5) | O12—C12 | 1.313 (5) |
N1—H1A | 0.8900 | N2—H2A | 0.8900 |
N1—H1B | 0.8900 | N2—H2B | 0.8900 |
N1—H1C | 0.8900 | N2—H2C | 0.8900 |
N1—C2 | 1.488 (5) | N2—C22 | 1.494 (5) |
C1—C2 | 1.503 (7) | O22—C12 | 1.185 (5) |
C2—H2 | 0.9800 | C12—C22 | 1.514 (7) |
C2—C3 | 1.522 (6) | C7—C8 | 1.475 (7) |
C102—C92 | 1.472 (7) | C22—H22 | 0.9800 |
C3—H3 | 0.9800 | C22—C32 | 1.518 (6) |
C3—C4 | 1.529 (6) | C9—H9 | 0.9300 |
C3—C5 | 1.524 (7) | C9—C10 | 1.485 (6) |
C92—H92 | 0.9300 | C9—C8 | 1.334 (6) |
C92—C82 | 1.349 (5) | C32—H32 | 0.9800 |
C82—H82 | 0.9300 | C32—C52 | 1.529 (7) |
C82—C72 | 1.490 (6) | C32—C42 | 1.517 (7) |
C4—H4A | 0.9600 | C52—H52A | 0.9700 |
C4—H4B | 0.9600 | C52—H52B | 0.9700 |
C4—H4C | 0.9600 | C52—C62 | 1.515 (7) |
C5—H5A | 0.9700 | C8—H8 | 0.9300 |
C5—H5B | 0.9700 | C62—H62A | 0.9600 |
C5—C6 | 1.501 (8) | C62—H62B | 0.9600 |
C6—H6A | 0.9600 | C62—H62C | 0.9600 |
C6—H6B | 0.9600 | C42—H42A | 0.9600 |
C6—H6C | 0.9600 | C42—H42B | 0.9600 |
O5—C10 | 1.249 (5) | C42—H42C | 0.9600 |
| | | |
C1—O1—H1 | 109.5 | H1WA—O1W1—H1WB | 109.5 |
C102—O62—H62 | 109.5 | C12—O12—H12 | 109.5 |
H1A—N1—H1B | 109.5 | H2A—N2—H2B | 109.5 |
H1A—N1—H1C | 109.5 | H2A—N2—H2C | 109.5 |
H1B—N1—H1C | 109.5 | H2B—N2—H2C | 109.5 |
C2—N1—H1A | 109.5 | C22—N2—H2A | 109.5 |
C2—N1—H1B | 109.5 | C22—N2—H2B | 109.5 |
C2—N1—H1C | 109.5 | C22—N2—H2C | 109.5 |
O1—C1—C2 | 115.1 (4) | O12—C12—C22 | 111.7 (4) |
O2—C1—O1 | 123.4 (5) | O22—C12—O12 | 123.3 (5) |
O2—C1—C2 | 121.5 (4) | O22—C12—C22 | 125.0 (4) |
N1—C2—C1 | 111.1 (3) | O3—C7—O4 | 122.6 (5) |
N1—C2—H2 | 106.9 | O3—C7—C8 | 116.2 (5) |
N1—C2—C3 | 111.2 (4) | O4—C7—C8 | 121.2 (4) |
C1—C2—H2 | 106.9 | N2—C22—C12 | 106.7 (4) |
C1—C2—C3 | 113.6 (4) | N2—C22—H22 | 107.8 |
C3—C2—H2 | 106.9 | N2—C22—C32 | 113.3 (4) |
O52—C102—O62 | 121.3 (5) | C12—C22—H22 | 107.8 |
O52—C102—C92 | 117.1 (4) | C12—C22—C32 | 113.3 (4) |
O62—C102—C92 | 121.6 (4) | C32—C22—H22 | 107.8 |
C2—C3—H3 | 107.1 | C10—C9—H9 | 114.8 |
C2—C3—C4 | 112.7 (4) | C8—C9—H9 | 114.8 |
C2—C3—C5 | 112.8 (5) | C8—C9—C10 | 130.4 (5) |
C4—C3—H3 | 107.1 | C22—C32—H32 | 106.8 |
C5—C3—H3 | 107.1 | C22—C32—C52 | 112.7 (4) |
C5—C3—C4 | 109.7 (4) | C52—C32—H32 | 106.8 |
C102—C92—H92 | 115.1 | C42—C32—C22 | 111.5 (5) |
C82—C92—C102 | 129.8 (5) | C42—C32—H32 | 106.8 |
C82—C92—H92 | 115.1 | C42—C32—C52 | 111.7 (4) |
C92—C82—H82 | 115.2 | O5—C10—O6 | 121.3 (5) |
C92—C82—C72 | 129.7 (5) | O5—C10—C9 | 118.3 (5) |
C72—C82—H82 | 115.2 | O6—C10—C9 | 120.4 (5) |
O42—C72—C82 | 120.5 (4) | C32—C52—H52A | 108.7 |
O32—C72—O42 | 122.8 (5) | C32—C52—H52B | 108.7 |
O32—C72—C82 | 116.8 (5) | H52A—C52—H52B | 107.6 |
C3—C4—H4A | 109.5 | C62—C52—C32 | 114.4 (5) |
C3—C4—H4B | 109.5 | C62—C52—H52A | 108.7 |
C3—C4—H4C | 109.5 | C62—C52—H52B | 108.7 |
H4A—C4—H4B | 109.5 | C7—C8—H8 | 115.1 |
H4A—C4—H4C | 109.5 | C9—C8—C7 | 129.9 (5) |
H4B—C4—H4C | 109.5 | C9—C8—H8 | 115.1 |
C3—C5—H5A | 108.2 | C52—C62—H62A | 109.5 |
C3—C5—H5B | 108.2 | C52—C62—H62B | 109.5 |
H5A—C5—H5B | 107.4 | C52—C62—H62C | 109.5 |
C6—C5—C3 | 116.3 (5) | H62A—C62—H62B | 109.5 |
C6—C5—H5A | 108.2 | H62A—C62—H62C | 109.5 |
C6—C5—H5B | 108.2 | H62B—C62—H62C | 109.5 |
C5—C6—H6A | 109.5 | C32—C42—H42A | 109.5 |
C5—C6—H6B | 109.5 | C32—C42—H42B | 109.5 |
C5—C6—H6C | 109.5 | C32—C42—H42C | 109.5 |
H6A—C6—H6B | 109.5 | H42A—C42—H42B | 109.5 |
H6A—C6—H6C | 109.5 | H42A—C42—H42C | 109.5 |
H6B—C6—H6C | 109.5 | H42B—C42—H42C | 109.5 |
C10—O6—H6 | 109.5 | | |
| | | |
O1—C1—C2—N1 | −20.4 (6) | O3—C7—C8—C9 | 179.0 (5) |
O1—C1—C2—C3 | 105.8 (5) | O4—C7—C8—C9 | −1.3 (9) |
O52—C102—C92—C82 | 178.8 (5) | O12—C12—C22—N2 | 167.6 (4) |
O2—C1—C2—N1 | 161.0 (5) | O12—C12—C22—C32 | −67.1 (5) |
O2—C1—C2—C3 | −72.8 (6) | N2—C22—C32—C52 | 55.9 (6) |
O62—C102—C92—C82 | 0.2 (8) | N2—C22—C32—C42 | −70.7 (6) |
N1—C2—C3—C4 | 66.5 (5) | O22—C12—C22—N2 | −13.3 (7) |
N1—C2—C3—C5 | −168.6 (4) | O22—C12—C22—C32 | 112.0 (6) |
C1—C2—C3—C4 | −59.7 (6) | C12—C22—C32—C52 | −65.8 (5) |
C1—C2—C3—C5 | 65.3 (5) | C12—C22—C32—C42 | 167.6 (4) |
C2—C3—C5—C6 | 54.5 (8) | C22—C32—C52—C62 | 167.7 (5) |
C102—C92—C82—C72 | −0.2 (9) | C10—C9—C8—C7 | −0.6 (10) |
C92—C82—C72—O42 | −3.2 (8) | C8—C9—C10—O5 | −179.0 (5) |
C92—C82—C72—O32 | 176.7 (5) | C8—C9—C10—O6 | 1.1 (9) |
C4—C3—C5—C6 | −178.9 (6) | C42—C32—C52—C62 | −65.9 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O52i | 0.82 | 1.82 | 2.619 (5) | 166 |
O62—H62···O42 | 0.82 | 1.59 | 2.410 (5) | 177 |
N1—H1A···O5ii | 0.89 | 2.03 | 2.871 (5) | 158 |
N1—H1C···O5 | 0.89 | 1.92 | 2.796 (5) | 168 |
O6—H6···O4 | 0.82 | 1.60 | 2.418 (4) | 179 |
O1W1—H1WA···O32iii | 0.85 | 1.96 | 2.756 (5) | 155 |
O12—H12···O3iv | 0.82 | 1.78 | 2.594 (5) | 175 |
N2—H2A···O32 | 0.89 | 2.05 | 2.881 (5) | 155 |
N2—H2B···O1W1iii | 0.89 | 2.03 | 2.892 (6) | 163 |
N2—H2C···O1W1v | 0.89 | 1.94 | 2.780 (5) | 157 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x, y+1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) x, y+1, z−1; (v) x, y, z−1. |
(III)
L-Norvalinium hydrogen maleate–
L-norvaline (1/1)
top
Crystal data top
C5H11NO2+·C4H3O4−·C5H12NO2 | F(000) = 376 |
Mr = 350.37 | Dx = 1.260 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2269 (6) Å | Cell parameters from 2037 reflections |
b = 5.30779 (17) Å | θ = 1.8–28.2° |
c = 15.4678 (6) Å | µ = 0.10 mm−1 |
β = 113.055 (5)° | T = 298 K |
V = 923.65 (7) Å3 | Plate, clear light colourless |
Z = 2 | 0.5 × 0.13 × 0.05 mm |
Data collection top
Agilent Xcalibur Gemini Ultra diffractometer with Ruby detector | 3014 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2642 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −6→5 |
Tmin = 0.900, Tmax = 1.000 | l = −19→19 |
5895 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1421P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3014 reflections | Δρmax = 0.29 e Å−3 |
262 parameters | Δρmin = −0.24 e Å−3 |
59 restraints | |
Special details top
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 | Uiso*/Ueq | Occ. (<1) |
N2 | 0.5847 (2) | 0.1724 (5) | 0.80036 (16) | 0.0383 (6) | |
H2A | 0.5959 | 0.3044 | 0.7693 | 0.046* | |
H2B | 0.5111 | 0.1763 | 0.7987 | 0.046* | |
H2C | 0.5952 | 0.0309 | 0.7737 | 0.046* | |
O2 | 0.37615 (18) | 0.2209 (4) | 0.83252 (15) | 0.0415 (5) | |
O5 | 0.5965 (2) | 0.6802 (5) | 0.70792 (15) | 0.0545 (7) | |
O21 | 0.59257 (19) | 0.5987 (4) | 0.89350 (15) | 0.0428 (6) | |
O11 | 0.7387 (2) | 0.4643 (5) | 1.02484 (14) | 0.0477 (6) | |
O1 | 0.2532 (2) | 0.3646 (5) | 0.89580 (16) | 0.0475 (6) | |
H1 | 0.2685 | 0.2297 | 0.9239 | 0.071* | |
N1 | 0.3696 (2) | 0.6466 (5) | 0.73896 (17) | 0.0377 (6) | |
H1A | 0.3495 | 0.5204 | 0.6978 | 0.045* | |
H1B | 0.4459 | 0.6323 | 0.7770 | 0.045* | |
H1C | 0.3580 | 0.7926 | 0.7084 | 0.045* | |
O3 | 0.6529 (2) | 0.6476 (6) | 0.36432 (15) | 0.0588 (7) | |
C11 | 0.6641 (3) | 0.4389 (6) | 0.9399 (2) | 0.0335 (7) | |
O6 | 0.6659 (4) | 0.9279 (5) | 0.6289 (2) | 0.0856 (11) | |
H6 | 0.6798 | 0.9226 | 0.5812 | 0.128* | |
C9 | 0.6295 (3) | 0.7140 (7) | 0.6429 (2) | 0.0441 (8) | |
O4 | 0.6878 (3) | 0.9153 (6) | 0.4798 (2) | 0.0804 (10) | |
C21 | 0.6714 (3) | 0.1820 (6) | 0.8997 (2) | 0.0363 (7) | |
H21 | 0.6462 | 0.0571 | 0.9348 | 0.044* | |
C1 | 0.3117 (3) | 0.3830 (6) | 0.8442 (2) | 0.0322 (6) | |
C8 | 0.6291 (4) | 0.5024 (7) | 0.5828 (3) | 0.0594 (11) | |
H8 | 0.6175 | 0.3462 | 0.6051 | 0.071* | |
C6 | 0.6611 (3) | 0.6944 (7) | 0.4442 (2) | 0.0439 (8) | |
C7 | 0.6423 (4) | 0.4942 (7) | 0.5016 (3) | 0.0576 (10) | |
H7 | 0.6391 | 0.3331 | 0.4771 | 0.069* | |
C2 | 0.2950 (3) | 0.6375 (6) | 0.7955 (2) | 0.0370 (7) | |
H2 | 0.3253 | 0.7663 | 0.8446 | 0.044* | |
C3 | 0.1667 (3) | 0.7012 (9) | 0.7366 (3) | 0.0658 (11) | |
H3AA | 0.1239 | 0.7106 | 0.7777 | 0.079* | 0.901 (9) |
H3AB | 0.1640 | 0.8672 | 0.7096 | 0.079* | 0.901 (9) |
H3BC | 0.1311 | 0.5361 | 0.7183 | 0.079* | 0.099 (9) |
H3BD | 0.1381 | 0.7600 | 0.7833 | 0.079* | 0.099 (9) |
C4 | 0.1047 (4) | 0.5257 (14) | 0.6609 (4) | 0.086 (2) | 0.901 (9) |
H4A | 0.1088 | 0.3580 | 0.6869 | 0.103* | 0.901 (9) |
H4B | 0.1443 | 0.5216 | 0.6174 | 0.103* | 0.901 (9) |
C5 | −0.0261 (6) | 0.598 (2) | 0.6071 (6) | 0.160 (5) | 0.901 (9) |
H5A | −0.0627 | 0.4800 | 0.5569 | 0.239* | 0.901 (9) |
H5B | −0.0307 | 0.7642 | 0.5817 | 0.239* | 0.901 (9) |
H5C | −0.0666 | 0.5938 | 0.6491 | 0.239* | 0.901 (9) |
C4B | 0.106 (4) | 0.837 (10) | 0.664 (4) | 0.078 (7) | 0.099 (9) |
H4BA | 0.1374 | 0.7954 | 0.6172 | 0.094* | 0.099 (9) |
H4BB | 0.1311 | 1.0096 | 0.6831 | 0.094* | 0.099 (9) |
C5B | −0.025 (4) | 0.850 (12) | 0.613 (4) | 0.086 (10) | 0.099 (9) |
H5BA | −0.0515 | 0.7100 | 0.5699 | 0.130* | 0.099 (9) |
H5BB | −0.0465 | 1.0045 | 0.5780 | 0.130* | 0.099 (9) |
H5BC | −0.0630 | 0.8420 | 0.6566 | 0.130* | 0.099 (9) |
C31 | 0.7941 (3) | 0.1072 (8) | 0.9071 (2) | 0.0528 (9) | |
H31A | 0.8465 | 0.1007 | 0.9731 | 0.063* | 0.954 (7) |
H31B | 0.7899 | −0.0614 | 0.8819 | 0.063* | 0.954 (7) |
H31C | 0.8378 | 0.2630 | 0.9288 | 0.063* | 0.046 (7) |
H31D | 0.8203 | −0.0005 | 0.9622 | 0.063* | 0.046 (7) |
C41 | 0.8479 (4) | 0.2757 (10) | 0.8583 (3) | 0.0665 (14) | 0.954 (7) |
H41A | 0.8574 | 0.4427 | 0.8858 | 0.080* | 0.954 (7) |
H41B | 0.7947 | 0.2891 | 0.7927 | 0.080* | 0.954 (7) |
C51 | 0.9687 (5) | 0.1791 (18) | 0.8650 (5) | 0.124 (3) | 0.954 (7) |
H51A | 1.0172 | 0.1394 | 0.9293 | 0.186* | 0.954 (7) |
H51B | 1.0070 | 0.3066 | 0.8429 | 0.186* | 0.954 (7) |
H51C | 0.9576 | 0.0305 | 0.8272 | 0.186* | 0.954 (7) |
C4B1 | 0.851 (7) | 0.008 (17) | 0.859 (6) | 0.049 (6) | 0.046 (7) |
H4BC | 0.7986 | 0.0618 | 0.7962 | 0.059* | 0.046 (7) |
H4BD | 0.8301 | −0.1678 | 0.8610 | 0.059* | 0.046 (7) |
C5B1 | 0.956 (6) | −0.026 (17) | 0.843 (7) | 0.047 (11) | 0.046 (7) |
H5BD | 0.9406 | −0.1343 | 0.7895 | 0.071* | 0.046 (7) |
H5BE | 0.9839 | 0.1344 | 0.8307 | 0.071* | 0.046 (7) |
H5BF | 1.0163 | −0.1011 | 0.8972 | 0.071* | 0.046 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N2 | 0.0404 (13) | 0.0370 (15) | 0.0414 (13) | −0.0062 (12) | 0.0203 (11) | −0.0116 (14) |
O2 | 0.0490 (12) | 0.0336 (12) | 0.0503 (13) | 0.0039 (11) | 0.0284 (10) | 0.0039 (12) |
O5 | 0.0732 (16) | 0.0565 (17) | 0.0429 (12) | 0.0016 (14) | 0.0326 (12) | −0.0022 (14) |
O21 | 0.0496 (12) | 0.0336 (13) | 0.0406 (11) | 0.0005 (10) | 0.0125 (10) | −0.0051 (11) |
O11 | 0.0598 (14) | 0.0464 (15) | 0.0304 (11) | 0.0070 (12) | 0.0107 (10) | −0.0059 (12) |
O1 | 0.0649 (15) | 0.0398 (14) | 0.0538 (14) | 0.0116 (12) | 0.0406 (13) | 0.0154 (12) |
N1 | 0.0420 (13) | 0.0356 (15) | 0.0378 (13) | −0.0023 (12) | 0.0183 (11) | 0.0074 (13) |
O3 | 0.0774 (16) | 0.068 (2) | 0.0360 (12) | −0.0014 (16) | 0.0282 (11) | 0.0020 (15) |
C11 | 0.0415 (16) | 0.0308 (17) | 0.0322 (15) | −0.0017 (14) | 0.0187 (14) | −0.0006 (15) |
O6 | 0.176 (3) | 0.0359 (16) | 0.073 (2) | −0.016 (2) | 0.079 (2) | −0.0111 (16) |
C9 | 0.059 (2) | 0.0364 (19) | 0.0395 (17) | 0.0081 (17) | 0.0220 (15) | 0.0016 (17) |
O4 | 0.153 (3) | 0.0392 (16) | 0.0747 (19) | −0.0067 (18) | 0.072 (2) | 0.0028 (16) |
C21 | 0.0451 (16) | 0.0324 (17) | 0.0333 (15) | 0.0003 (14) | 0.0175 (13) | −0.0007 (15) |
C1 | 0.0349 (15) | 0.0327 (17) | 0.0294 (14) | −0.0002 (13) | 0.0132 (12) | −0.0018 (14) |
C8 | 0.108 (3) | 0.0307 (19) | 0.055 (2) | 0.001 (2) | 0.048 (2) | 0.0042 (18) |
C6 | 0.0545 (19) | 0.041 (2) | 0.0397 (17) | 0.0033 (17) | 0.0217 (15) | 0.0010 (17) |
C7 | 0.102 (3) | 0.0314 (19) | 0.054 (2) | 0.002 (2) | 0.046 (2) | −0.0048 (18) |
C2 | 0.0485 (16) | 0.0326 (17) | 0.0365 (15) | 0.0065 (14) | 0.0235 (13) | 0.0067 (15) |
C3 | 0.061 (2) | 0.069 (3) | 0.074 (2) | 0.021 (2) | 0.033 (2) | 0.033 (3) |
C4 | 0.051 (3) | 0.114 (5) | 0.078 (3) | 0.006 (3) | 0.009 (2) | 0.001 (4) |
C5 | 0.059 (4) | 0.244 (13) | 0.129 (6) | 0.017 (6) | −0.013 (4) | 0.003 (8) |
C4B | 0.061 (10) | 0.072 (12) | 0.088 (11) | 0.016 (10) | 0.014 (9) | 0.039 (10) |
C5B | 0.065 (13) | 0.079 (16) | 0.095 (16) | 0.014 (14) | 0.008 (12) | 0.037 (14) |
C31 | 0.0509 (19) | 0.051 (2) | 0.0521 (19) | 0.0119 (18) | 0.0161 (16) | −0.0088 (19) |
C41 | 0.050 (2) | 0.079 (4) | 0.076 (3) | 0.001 (2) | 0.030 (2) | 0.000 (3) |
C51 | 0.059 (3) | 0.178 (9) | 0.151 (6) | 0.009 (5) | 0.058 (4) | 0.003 (7) |
C4B1 | 0.048 (10) | 0.048 (12) | 0.053 (11) | 0.006 (11) | 0.021 (9) | −0.011 (11) |
C5B1 | 0.034 (19) | 0.04 (2) | 0.07 (2) | −0.027 (19) | 0.024 (16) | −0.01 (2) |
Geometric parameters (Å, º) top
N2—H2A | 0.8900 | C3—C4 | 1.456 (7) |
N2—H2B | 0.8900 | C3—C4B | 1.29 (4) |
N2—H2C | 0.8900 | C4—H4A | 0.9700 |
N2—C21 | 1.487 (4) | C4—H4B | 0.9700 |
O2—C1 | 1.227 (4) | C4—C5 | 1.533 (8) |
O5—C9 | 1.234 (4) | C5—H5A | 0.9600 |
O21—C11 | 1.228 (4) | C5—H5B | 0.9600 |
O11—C11 | 1.279 (4) | C5—H5C | 0.9600 |
O1—H1 | 0.8200 | C4B—H4BA | 0.9700 |
O1—C1 | 1.268 (3) | C4B—H4BB | 0.9700 |
N1—H1A | 0.8900 | C4B—C5B | 1.49 (6) |
N1—H1B | 0.8900 | C5B—H5BA | 0.9600 |
N1—H1C | 0.8900 | C5B—H5BB | 0.9600 |
N1—C2 | 1.491 (3) | C5B—H5BC | 0.9600 |
O3—C6 | 1.226 (4) | C31—H31A | 0.9700 |
C11—C21 | 1.516 (4) | C31—H31B | 0.9700 |
O6—H6 | 0.8200 | C31—H31C | 0.9700 |
O6—C9 | 1.269 (4) | C31—H31D | 0.9700 |
C9—C8 | 1.457 (5) | C31—C41 | 1.480 (6) |
O4—C6 | 1.282 (5) | C31—C4B1 | 1.32 (7) |
C21—H21 | 0.9800 | C41—H41A | 0.9700 |
C21—C31 | 1.512 (4) | C41—H41B | 0.9700 |
C1—C2 | 1.521 (4) | C41—C51 | 1.528 (6) |
C8—H8 | 0.9300 | C51—H51A | 0.9600 |
C8—C7 | 1.329 (5) | C51—H51B | 0.9600 |
C6—C7 | 1.459 (5) | C51—H51C | 0.9600 |
C7—H7 | 0.9300 | C4B1—H4BC | 0.9700 |
C2—H2 | 0.9800 | C4B1—H4BD | 0.9700 |
C2—C3 | 1.512 (5) | C4B1—C5B1 | 1.41 (10) |
C3—H3AA | 0.9700 | C5B1—H5BD | 0.9600 |
C3—H3AB | 0.9700 | C5B1—H5BE | 0.9600 |
C3—H3BC | 0.9700 | C5B1—H5BF | 0.9600 |
C3—H3BD | 0.9700 | | |
| | | |
H2A—N2—H2B | 109.5 | C3—C4—C5 | 112.4 (6) |
H2A—N2—H2C | 109.5 | H4A—C4—H4B | 107.9 |
H2B—N2—H2C | 109.5 | C5—C4—H4A | 109.1 |
C21—N2—H2A | 109.5 | C5—C4—H4B | 109.1 |
C21—N2—H2B | 109.5 | C4—C5—H5A | 109.5 |
C21—N2—H2C | 109.5 | C4—C5—H5B | 109.5 |
C1—O1—H1 | 109.5 | C4—C5—H5C | 109.5 |
H1A—N1—H1B | 109.5 | H5A—C5—H5B | 109.5 |
H1A—N1—H1C | 109.5 | H5A—C5—H5C | 109.5 |
H1B—N1—H1C | 109.5 | H5B—C5—H5C | 109.5 |
C2—N1—H1A | 109.5 | C3—C4B—H4BA | 105.3 |
C2—N1—H1B | 109.5 | C3—C4B—H4BB | 105.3 |
C2—N1—H1C | 109.5 | C3—C4B—C5B | 128 (4) |
O21—C11—O11 | 125.9 (3) | H4BA—C4B—H4BB | 106.0 |
O21—C11—C21 | 121.6 (3) | C5B—C4B—H4BA | 105.3 |
O11—C11—C21 | 112.5 (3) | C5B—C4B—H4BB | 105.3 |
C9—O6—H6 | 109.5 | C4B—C5B—H5BA | 109.5 |
O5—C9—O6 | 121.2 (3) | C4B—C5B—H5BB | 109.5 |
O5—C9—C8 | 119.2 (3) | C4B—C5B—H5BC | 109.5 |
O6—C9—C8 | 119.6 (3) | H5BA—C5B—H5BB | 109.5 |
N2—C21—C11 | 108.8 (3) | H5BA—C5B—H5BC | 109.5 |
N2—C21—H21 | 107.4 | H5BB—C5B—H5BC | 109.5 |
N2—C21—C31 | 110.8 (2) | C21—C31—H31A | 108.4 |
C11—C21—H21 | 107.4 | C21—C31—H31B | 108.4 |
C31—C21—C11 | 114.9 (3) | C21—C31—H31C | 101.4 |
C31—C21—H21 | 107.4 | C21—C31—H31D | 101.4 |
O2—C1—O1 | 126.3 (3) | H31A—C31—H31B | 107.5 |
O2—C1—C2 | 121.3 (2) | H31C—C31—H31D | 104.6 |
O1—C1—C2 | 112.4 (3) | C41—C31—C21 | 115.3 (3) |
C9—C8—H8 | 114.4 | C41—C31—H31A | 108.4 |
C7—C8—C9 | 131.1 (4) | C41—C31—H31B | 108.4 |
C7—C8—H8 | 114.4 | C4B1—C31—C21 | 142 (4) |
O3—C6—O4 | 121.6 (4) | C4B1—C31—H31C | 101.4 |
O3—C6—C7 | 119.7 (4) | C4B1—C31—H31D | 101.4 |
O4—C6—C7 | 118.7 (3) | C31—C41—H41A | 109.2 |
C8—C7—C6 | 131.1 (4) | C31—C41—H41B | 109.2 |
C8—C7—H7 | 114.4 | C31—C41—C51 | 111.9 (5) |
C6—C7—H7 | 114.4 | H41A—C41—H41B | 107.9 |
N1—C2—C1 | 108.9 (2) | C51—C41—H41A | 109.2 |
N1—C2—H2 | 107.4 | C51—C41—H41B | 109.2 |
N1—C2—C3 | 111.6 (3) | C41—C51—H51A | 109.5 |
C1—C2—H2 | 107.4 | C41—C51—H51B | 109.5 |
C3—C2—C1 | 113.8 (3) | C41—C51—H51C | 109.5 |
C3—C2—H2 | 107.4 | H51A—C51—H51B | 109.5 |
C2—C3—H3AA | 108.4 | H51A—C51—H51C | 109.5 |
C2—C3—H3AB | 108.4 | H51B—C51—H51C | 109.5 |
C2—C3—H3BC | 102.4 | C31—C4B1—H4BC | 99.1 |
C2—C3—H3BD | 102.4 | C31—C4B1—H4BD | 99.1 |
H3AA—C3—H3AB | 107.4 | C31—C4B1—C5B1 | 150 (7) |
H3BC—C3—H3BD | 104.9 | H4BC—C4B1—H4BD | 103.9 |
C4—C3—C2 | 115.6 (4) | C5B1—C4B1—H4BC | 99.1 |
C4—C3—H3AA | 108.4 | C5B1—C4B1—H4BD | 99.1 |
C4—C3—H3AB | 108.4 | C4B1—C5B1—H5BD | 109.5 |
C4B—C3—C2 | 139 (2) | C4B1—C5B1—H5BE | 109.5 |
C4B—C3—H3BC | 102.4 | C4B1—C5B1—H5BF | 109.5 |
C4B—C3—H3BD | 102.4 | H5BD—C5B1—H5BE | 109.5 |
C3—C4—H4A | 109.1 | H5BD—C5B1—H5BF | 109.5 |
C3—C4—H4B | 109.1 | H5BE—C5B1—H5BF | 109.5 |
| | | |
N2—C21—C31—C41 | 63.3 (4) | O3—C6—C7—C8 | −168.8 (5) |
N2—C21—C31—C4B1 | −11 (7) | C11—C21—C31—C41 | −60.4 (4) |
O2—C1—C2—N1 | −1.6 (4) | C11—C21—C31—C4B1 | −135 (7) |
O2—C1—C2—C3 | 123.7 (3) | O6—C9—C8—C7 | −12.9 (7) |
O5—C9—C8—C7 | 168.5 (4) | C9—C8—C7—C6 | −0.5 (8) |
O21—C11—C21—N2 | 2.0 (4) | O4—C6—C7—C8 | 12.2 (7) |
O21—C11—C21—C31 | 126.8 (3) | C21—C31—C41—C51 | −177.0 (4) |
O11—C11—C21—N2 | −178.2 (2) | C21—C31—C4B1—C5B1 | 156 (12) |
O11—C11—C21—C31 | −53.4 (4) | C1—C2—C3—C4 | −59.6 (5) |
O1—C1—C2—N1 | 178.1 (3) | C1—C2—C3—C4B | −154 (4) |
O1—C1—C2—C3 | −56.7 (4) | C2—C3—C4—C5 | 177.7 (6) |
N1—C2—C3—C4 | 64.2 (5) | C2—C3—C4B—C5B | 173 (4) |
N1—C2—C3—C4B | −30 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O2 | 0.89 | 1.93 | 2.794 (3) | 163 |
N2—H2C···O5i | 0.89 | 2.12 | 3.009 (4) | 172 |
O1—H1···O11ii | 0.82 | 1.64 | 2.437 (3) | 165 |
N1—H1B···O21 | 0.89 | 1.99 | 2.847 (3) | 161 |
O6—H6···O4 | 0.82 | 1.61 | 2.425 (4) | 172 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+2. |
C22(12) motifs in different amino acid maleates (see also Fig. 1).
The structures solved in this paper are highlighted in bold topNo. | Maleate (M) | CSD refcode (Groom & Allen, 2014) | Comments related to C22(12) motif |
1 | (GlyH)·M- | RENBAN | All these structures have C22(12) chains |
2 | (L-AlaH)·M- | BOQTEG | |
3 | (L-PheH)·M- | EDAXIQ | |
4 | (DL-PheH·M- | VAGVIJ | |
5 | (DL-ValH)·M- | QURSUR | |
6 | (L-SerH)·M- | REZPET | |
7 | (DL-SerH)·M- | REZPAP | |
8 | (DL-MetH)·M- | MOCXUX | |
9 | (SarH)·M- | MIYBAX | |
10 | (L-HisH2)·(M-)2 | TENVOZ | This structure has L-histidinium2+ cation with the protonated
side chain and the protonated carboxylic acid group. This leads to the
formation
of C22(12)' which is very similar to C22(12) chains. |
11 | (DL-ThrH)·M- | ETEYOR | The second hydrogen bond is formed between the –OH group of amino acid
side chain and a carboxylate group of the maleate anion. This leads to
the formation of C22(12)' |
12 | (β-AlaH)·M- | EDASUX | The backbone of β-alaninium is one atom longer than common amino acids. This
leads to the formation of C22(13) chains |
13 | (L-LysH)·M- | XADTOL | The formation of C22(12) chains is impossible because the
carboxylic acid group of this amino acid is deprotonated, while the group
of the side chain is protonated |
14 | (L-ArgH)·M-·H2O | GIHGEK | |
15 | (DL-ArgH)·M- | · | |
16 | (L-HisH)2·(M-)2 | TENVUF | |
17 | (L-HisH)·M-·H2O | VAZJUD | |
18 | (L-HisH)2·(M-)2·3H2O | | |
19 | (BetH)·M- | NASQED01 | C22(12) chains cannot be formed because amino group of betaine is
completely methylated |
20 | (L-IleH)2·(M-)2·H2O,(II) | | C44(24) are formed by two non-equivalent
L-IleH cations and
two
maleate anions |
21 | (L-LeuH)3·(M-)3, (I) | | C66(36) are formed by three non-equivalent
L-LeuH cations and three
maleate anions |
22 | L-Met·L-MetH·M- | ** | C33(17) is formed by L-Met···L-MetH
(case 22) or L-Nva···L-NvaH (case 23) dications |
23 | L-Nva·L-NvaH·M-, (III) | | |
Notes: (*) for (DL-ArgH)·M-, the coordinates were taken from
Ravishankar et al. (1998); (**) the atomic coordinates of
L-Met·L-MetH·M- were not found in the
papers by Natarajan et al. (2008, 2010) and in the
Cambridge Structural Database( Version 5.35, updates to February 2014;
Groom & Allen, 2014),
but in the Fig. 3 in Natarajan et al. (2008),
a C33(17) motif can be seen. |