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Crystals of maleates of three amino acids with hydrophobic side chains [L-leu­cenium hydrogen maleate, C6H14NO2+·C4H3O4-, (I), L-iso­leucenium hydro­gen maleate hemihydrate, C6H14NO2+·C4H3O4-·0.5H2O, (II), and L-norvalinium hydrogen maleate-L-norvaline (1/1), C5H11NO2+·C4H3O4-·C5H12NO2, (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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615010888/sk3586sup1.cif
Contains datablocks I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010888/sk3586Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010888/sk3586IIsup4.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010888/sk3586IIIsup3.hkl
Contains datablock III

CCDC references: 1405139; 1405138; 1405137

Computing details top

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+·C4H3O4F(000) = 1584
Mr = 247.24Dx = 1.265 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 21.7231 (19) ÅCell parameters from 1466 reflections
b = 5.6603 (4) Åθ = 1.9–18.4°
c = 32.075 (3) ŵ = 0.11 mm1
β = 98.950 (8)°T = 298 K
V = 3895.8 (6) Å3Needle, clear light colourless
Z = 122.5 × 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 Source2843 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.182
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.9°
ω scansh = 2626
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 77
Tmin = 0.345, Tmax = 1.000l = 4040
24642 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.087H-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 reflectionsΔρmax = 0.17 e Å3
474 parametersΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
O510.5051 (3)0.7078 (12)0.2477 (2)0.071 (2)
O210.7040 (3)0.5468 (12)0.50318 (18)0.0555 (19)
O310.6155 (3)0.5850 (13)0.4185 (2)0.071 (2)
O420.2768 (3)0.5282 (12)0.64712 (19)0.057 (2)
O610.5348 (4)0.4129 (12)0.29051 (19)0.065 (2)
H610.55410.39330.31430.098*
O520.3502 (3)0.3342 (12)0.7754 (2)0.076 (2)
O220.5068 (3)0.4577 (13)0.8488 (2)0.063 (2)
N20.5063 (3)0.1572 (12)0.7876 (2)0.049 (2)
H2A0.48880.26500.76930.058*
H2B0.48250.13530.80750.058*
H2C0.51000.02160.77410.058*
O120.6052 (3)0.5617 (14)0.8508 (3)0.081 (2)
H120.59520.68080.86270.121*
O530.4151 (3)0.1556 (12)0.0645 (2)0.072 (2)
O330.4157 (3)0.0606 (12)0.1078 (2)0.069 (2)
O620.3225 (4)0.5702 (12)0.7217 (2)0.068 (2)
H620.31620.56200.69590.102*
O630.4258 (4)0.1558 (13)0.0239 (2)0.090 (3)
H630.42940.18670.00140.135*
N30.9173 (3)0.1039 (13)0.8968 (2)0.051 (2)
H3A0.95020.11590.88350.062*
H3B0.91390.04430.90550.062*
H3C0.92220.20020.91900.062*
O130.8285 (3)0.4576 (15)0.8165 (2)0.081 (2)
H130.83570.59120.80870.121*
O320.2522 (3)0.2399 (12)0.6017 (2)0.075 (2)
O110.6421 (4)0.2531 (13)0.4744 (2)0.075 (2)
H110.63690.33930.45360.112*
O410.5815 (3)0.3584 (11)0.3639 (2)0.0547 (19)
O230.9291 (3)0.4450 (13)0.8418 (2)0.070 (2)
O430.4309 (5)0.2469 (13)0.0512 (2)0.100 (3)
C920.3095 (5)0.1521 (19)0.7125 (3)0.064 (3)
H920.31530.01180.72770.077*
C210.6919 (4)0.1973 (18)0.5438 (3)0.048 (3)
H210.69350.03130.53540.057*
C1020.3278 (5)0.3648 (19)0.7371 (3)0.054 (3)
C910.5486 (5)0.8120 (18)0.3168 (3)0.071 (4)
H910.54270.96900.30870.085*
N10.7531 (3)0.2711 (14)0.5680 (2)0.055 (2)
H1A0.78260.25420.55180.066*
H1B0.76210.18150.59090.066*
H1C0.75110.42180.57560.066*
C710.5914 (5)0.561 (2)0.3807 (3)0.054 (3)
C1010.5279 (5)0.6353 (18)0.2831 (3)0.054 (3)
C930.4223 (4)0.2234 (18)0.0083 (3)0.059 (3)
H930.42260.38400.00220.071*
C120.5557 (5)0.4345 (19)0.8382 (3)0.047 (3)
C220.5687 (4)0.2397 (18)0.8072 (3)0.047 (3)
H220.58960.10880.82380.056*
C830.4239 (5)0.1712 (17)0.0492 (3)0.061 (3)
H830.42650.30110.06710.073*
C730.4223 (5)0.0584 (19)0.0700 (4)0.059 (3)
C720.2706 (5)0.311 (2)0.6383 (3)0.052 (3)
C810.5743 (5)0.7793 (18)0.3569 (3)0.064 (3)
H810.58280.91760.37240.077*
C1030.4200 (5)0.066 (2)0.0291 (4)0.058 (3)
C130.8784 (5)0.3744 (19)0.8413 (3)0.053 (3)
C820.2857 (5)0.1262 (18)0.6718 (3)0.069 (3)
H820.27730.02860.66290.083*
C110.6809 (5)0.356 (2)0.5051 (3)0.049 (3)
C320.6093 (4)0.3118 (17)0.7742 (3)0.055 (3)
H32A0.58780.43660.75690.066*
H32B0.64780.37780.78880.066*
C430.7845 (5)0.041 (3)0.9172 (4)0.088 (4)
H430.82070.03300.93420.106*
C410.5781 (5)0.139 (2)0.5547 (4)0.082 (4)
H410.56480.21540.52730.099*
C230.8597 (4)0.1708 (18)0.8674 (3)0.051 (3)
H230.84610.03710.84890.061*
C610.5320 (5)0.213 (3)0.5829 (4)0.143 (7)
H61A0.54840.17570.61160.215*
H61B0.49340.13100.57470.215*
H61C0.52500.38050.58020.215*
C630.7483 (6)0.144 (2)0.8922 (5)0.141 (7)
H63A0.71340.07420.87450.211*
H63B0.73360.25630.91080.211*
H63C0.77440.22330.87500.211*
C330.8077 (4)0.2381 (18)0.8920 (3)0.053 (3)
H33A0.82240.36580.91120.063*
H33B0.77280.29810.87230.063*
C310.6415 (5)0.2331 (19)0.5711 (3)0.064 (3)
H31A0.65550.16050.59830.077*
H31B0.63780.40130.57580.077*
C510.5769 (6)0.123 (2)0.5466 (5)0.148 (7)
H51A0.59280.20430.57230.223*
H51B0.60220.15840.52550.223*
H51C0.53480.17210.53700.223*
C530.7445 (6)0.158 (3)0.9478 (4)0.141 (7)
H53A0.71090.24500.93190.211*
H53B0.77010.26290.96660.211*
H53C0.72780.03720.96390.211*
C620.6695 (6)0.060 (2)0.7675 (5)0.132 (6)
H62A0.70800.01660.77870.199*
H62B0.67720.18080.74800.199*
H62C0.65150.12870.79020.199*
C420.6254 (5)0.119 (2)0.7451 (4)0.082 (4)
H420.58690.03740.73300.099*
C520.6536 (6)0.236 (3)0.7093 (4)0.132 (6)
H52A0.62730.36400.69780.197*
H52B0.65660.12170.68760.197*
H52C0.69430.29520.72010.197*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O510.100 (6)0.074 (5)0.033 (5)0.007 (5)0.011 (4)0.011 (4)
O210.087 (5)0.052 (4)0.025 (4)0.020 (4)0.003 (4)0.012 (4)
O310.089 (5)0.083 (6)0.031 (4)0.000 (5)0.021 (4)0.005 (4)
O420.095 (5)0.045 (5)0.028 (4)0.012 (4)0.002 (4)0.004 (4)
O610.105 (6)0.056 (5)0.024 (4)0.001 (5)0.024 (4)0.006 (4)
O520.116 (6)0.069 (5)0.034 (5)0.006 (5)0.011 (4)0.004 (4)
O220.067 (5)0.087 (5)0.037 (4)0.003 (5)0.017 (4)0.016 (4)
N20.065 (6)0.058 (5)0.025 (5)0.003 (5)0.011 (4)0.005 (4)
O120.093 (6)0.096 (7)0.058 (6)0.022 (6)0.025 (5)0.031 (5)
O530.106 (6)0.085 (6)0.024 (4)0.004 (5)0.004 (4)0.009 (4)
O330.112 (6)0.070 (5)0.027 (4)0.007 (5)0.013 (4)0.006 (4)
O620.120 (7)0.050 (5)0.030 (4)0.004 (5)0.002 (5)0.001 (4)
O630.178 (9)0.066 (6)0.024 (5)0.011 (6)0.005 (5)0.007 (4)
N30.065 (5)0.061 (6)0.031 (5)0.002 (5)0.014 (4)0.001 (4)
O130.093 (6)0.100 (7)0.046 (5)0.004 (6)0.003 (4)0.031 (5)
O320.124 (7)0.062 (5)0.029 (5)0.004 (5)0.016 (4)0.002 (4)
O110.101 (6)0.083 (6)0.028 (5)0.028 (5)0.025 (4)0.014 (4)
O410.076 (5)0.039 (4)0.043 (5)0.012 (4)0.008 (4)0.007 (4)
O230.071 (5)0.083 (6)0.055 (5)0.023 (5)0.008 (4)0.017 (5)
O430.215 (10)0.049 (5)0.040 (5)0.020 (6)0.032 (6)0.011 (4)
C920.102 (9)0.054 (8)0.034 (7)0.000 (7)0.004 (6)0.012 (6)
C210.059 (7)0.056 (7)0.028 (6)0.001 (6)0.005 (5)0.005 (5)
C1020.077 (8)0.046 (7)0.037 (7)0.002 (6)0.002 (6)0.010 (6)
C910.111 (10)0.049 (7)0.044 (8)0.005 (7)0.015 (7)0.009 (6)
N10.067 (6)0.077 (6)0.019 (5)0.014 (5)0.002 (4)0.014 (4)
C710.055 (7)0.057 (8)0.046 (8)0.005 (7)0.004 (6)0.015 (7)
C1010.080 (8)0.047 (7)0.034 (7)0.005 (6)0.006 (6)0.002 (6)
C930.093 (8)0.047 (6)0.034 (7)0.001 (6)0.002 (6)0.001 (6)
C120.067 (8)0.053 (7)0.022 (6)0.000 (7)0.008 (6)0.003 (5)
C220.042 (6)0.064 (7)0.031 (6)0.005 (6)0.005 (5)0.008 (6)
C830.086 (8)0.043 (7)0.049 (8)0.001 (6)0.001 (6)0.015 (6)
C730.087 (8)0.035 (6)0.057 (8)0.025 (7)0.014 (7)0.007 (7)
C720.062 (7)0.061 (8)0.030 (7)0.003 (7)0.001 (5)0.009 (6)
C810.101 (9)0.049 (7)0.038 (7)0.004 (7)0.007 (6)0.005 (6)
C1030.063 (7)0.058 (8)0.049 (8)0.010 (7)0.001 (6)0.008 (7)
C130.077 (8)0.061 (8)0.019 (6)0.006 (7)0.002 (6)0.005 (5)
C820.107 (9)0.051 (8)0.042 (8)0.008 (7)0.006 (7)0.004 (6)
C110.053 (7)0.071 (8)0.023 (6)0.003 (6)0.005 (5)0.011 (6)
C320.061 (7)0.078 (8)0.029 (6)0.006 (6)0.017 (5)0.005 (6)
C430.055 (8)0.113 (12)0.097 (11)0.014 (8)0.012 (8)0.036 (10)
C410.053 (8)0.122 (12)0.075 (10)0.006 (8)0.020 (7)0.029 (8)
C230.066 (7)0.066 (7)0.019 (6)0.005 (6)0.002 (5)0.000 (5)
C610.087 (10)0.240 (19)0.116 (14)0.027 (11)0.055 (10)0.022 (13)
C630.137 (14)0.090 (11)0.21 (2)0.046 (11)0.080 (13)0.025 (12)
C330.057 (7)0.066 (7)0.036 (6)0.004 (6)0.008 (5)0.001 (6)
C310.078 (8)0.083 (8)0.036 (7)0.008 (7)0.020 (6)0.004 (6)
C510.108 (12)0.094 (13)0.24 (2)0.020 (10)0.026 (12)0.022 (13)
C530.117 (12)0.219 (19)0.102 (13)0.013 (12)0.066 (10)0.013 (13)
C620.169 (15)0.093 (11)0.162 (16)0.031 (12)0.108 (13)0.009 (12)
C420.075 (9)0.113 (11)0.068 (9)0.016 (8)0.039 (7)0.030 (8)
C520.138 (12)0.214 (17)0.056 (10)0.011 (12)0.059 (9)0.013 (11)
Geometric parameters (Å, º) top
O51—C1011.234 (11)C93—C1031.489 (13)
O21—C111.199 (10)C12—C221.540 (12)
O31—C711.251 (11)C22—H220.9800
O42—C721.262 (11)C22—C321.536 (11)
O61—H610.8200C83—H830.9300
O61—C1011.286 (10)C83—C731.465 (13)
O52—C1021.262 (11)C72—C821.499 (13)
O22—C121.172 (10)C81—H810.9300
N2—H2A0.8900C13—C231.518 (13)
N2—H2B0.8900C82—H820.9300
N2—H2C0.8900C32—H32A0.9700
N2—C221.480 (10)C32—H32B0.9700
O12—H120.8200C32—C421.513 (13)
O12—C121.305 (10)C43—H430.9800
O53—C1031.233 (12)C43—C631.473 (16)
O33—C731.244 (11)C43—C331.507 (14)
O62—H620.8200C43—C531.556 (15)
O62—C1021.261 (11)C41—H410.9800
O63—H630.8200C41—C611.509 (15)
O63—C1031.269 (11)C41—C311.494 (13)
N3—H3A0.8900C41—C511.504 (16)
N3—H3B0.8900C23—H230.9800
N3—H3C0.8900C23—C331.523 (11)
N3—C231.494 (10)C61—H61A0.9600
O13—H130.8200C61—H61B0.9600
O13—C131.327 (11)C61—H61C0.9600
O32—C721.247 (11)C63—H63A0.9600
O11—H110.8200C63—H63B0.9600
O11—C111.325 (11)C63—H63C0.9600
O41—C711.271 (12)C33—H33A0.9700
O23—C131.170 (10)C33—H33B0.9700
O43—C731.254 (11)C31—H31A0.9700
C92—H920.9300C31—H31B0.9700
C92—C1021.459 (13)C51—H51A0.9600
C92—C821.337 (13)C51—H51B0.9600
C21—H210.9800C51—H51C0.9600
C21—N11.490 (10)C53—H53A0.9600
C21—C111.521 (12)C53—H53B0.9600
C21—C311.517 (11)C53—H53C0.9600
C91—H910.9300C62—H62A0.9600
C91—C1011.491 (13)C62—H62B0.9600
C91—C811.332 (13)C62—H62C0.9600
N1—H1A0.8900C62—C421.494 (16)
N1—H1B0.8900C42—H420.9800
N1—H1C0.8900C42—C521.535 (15)
C71—C811.470 (13)C52—H52A0.9600
C93—H930.9300C52—H52B0.9600
C93—C831.339 (12)C52—H52C0.9600
C101—O61—H61109.5O11—C11—C21110.5 (9)
H2A—N2—H2B109.5C22—C32—H32A108.2
H2A—N2—H2C109.5C22—C32—H32B108.2
H2B—N2—H2C109.5H32A—C32—H32B107.3
C22—N2—H2A109.5C42—C32—C22116.5 (8)
C22—N2—H2B109.5C42—C32—H32A108.2
C22—N2—H2C109.5C42—C32—H32B108.2
C12—O12—H12109.5C63—C43—H43108.1
C102—O62—H62109.5C63—C43—C33115.5 (12)
C103—O63—H63109.5C63—C43—C53110.0 (11)
H3A—N3—H3B109.5C33—C43—H43108.1
H3A—N3—H3C109.5C33—C43—C53107.0 (11)
H3B—N3—H3C109.5C53—C43—H43108.1
C23—N3—H3A109.5C61—C41—H41106.6
C23—N3—H3B109.5C31—C41—H41106.6
C23—N3—H3C109.5C31—C41—C61110.6 (11)
C13—O13—H13109.5C31—C41—C51113.6 (11)
C11—O11—H11109.5C51—C41—H41106.6
C102—C92—H92114.8C51—C41—C61112.4 (12)
C82—C92—H92114.8N3—C23—C13105.7 (8)
C82—C92—C102130.5 (10)N3—C23—H23109.3
N1—C21—H21110.3N3—C23—C33110.7 (7)
N1—C21—C11105.9 (8)C13—C23—H23109.3
N1—C21—C31109.2 (8)C13—C23—C33112.4 (8)
C11—C21—H21110.3C33—C23—H23109.3
C31—C21—H21110.3C41—C61—H61A109.5
C31—C21—C11110.8 (8)C41—C61—H61B109.5
O52—C102—C92116.3 (10)C41—C61—H61C109.5
O62—C102—O52120.3 (10)H61A—C61—H61B109.5
O62—C102—C92123.3 (10)H61A—C61—H61C109.5
C101—C91—H91115.1H61B—C61—H61C109.5
C81—C91—H91115.1C43—C63—H63A109.5
C81—C91—C101129.9 (10)C43—C63—H63B109.5
C21—N1—H1A109.5C43—C63—H63C109.5
C21—N1—H1B109.5H63A—C63—H63B109.5
C21—N1—H1C109.5H63A—C63—H63C109.5
H1A—N1—H1B109.5H63B—C63—H63C109.5
H1A—N1—H1C109.5C43—C33—C23115.4 (9)
H1B—N1—H1C109.5C43—C33—H33A108.4
O31—C71—O41121.8 (10)C43—C33—H33B108.4
O31—C71—C81116.5 (11)C23—C33—H33A108.4
O41—C71—C81121.7 (9)C23—C33—H33B108.4
O51—C101—O61120.9 (10)H33A—C33—H33B107.5
O51—C101—C91118.5 (10)C21—C31—H31A108.0
O61—C101—C91120.6 (10)C21—C31—H31B108.0
C83—C93—H93114.8C41—C31—C21117.3 (9)
C83—C93—C103130.4 (10)C41—C31—H31A108.0
C103—C93—H93114.8C41—C31—H31B108.0
O22—C12—O12126.1 (10)H31A—C31—H31B107.2
O22—C12—C22122.2 (10)C41—C51—H51A109.5
O12—C12—C22111.7 (9)C41—C51—H51B109.5
N2—C22—C12104.6 (7)C41—C51—H51C109.5
N2—C22—H22107.9H51A—C51—H51B109.5
N2—C22—C32112.1 (7)H51A—C51—H51C109.5
C12—C22—H22107.9H51B—C51—H51C109.5
C32—C22—C12116.0 (8)C43—C53—H53A109.5
C32—C22—H22107.9C43—C53—H53B109.5
C93—C83—H83115.0C43—C53—H53C109.5
C93—C83—C73130.1 (10)H53A—C53—H53B109.5
C73—C83—H83115.0H53A—C53—H53C109.5
O33—C73—O43120.6 (10)H53B—C53—H53C109.5
O33—C73—C83118.0 (10)H62A—C62—H62B109.5
O43—C73—C83121.3 (10)H62A—C62—H62C109.5
O42—C72—C82121.1 (10)H62B—C62—H62C109.5
O32—C72—O42122.2 (10)C42—C62—H62A109.5
O32—C72—C82116.7 (10)C42—C62—H62B109.5
C91—C81—C71130.7 (10)C42—C62—H62C109.5
C91—C81—H81114.7C32—C42—H42108.6
C71—C81—H81114.7C32—C42—C52107.8 (10)
O53—C103—O63121.4 (11)C62—C42—C32112.6 (11)
O53—C103—C93118.7 (10)C62—C42—H42108.6
O63—C103—C93119.7 (10)C62—C42—C52110.6 (10)
O13—C13—C23109.6 (9)C52—C42—H42108.6
O23—C13—O13124.6 (10)C42—C52—H52A109.5
O23—C13—C23125.8 (10)C42—C52—H52B109.5
C92—C82—C72129.2 (10)C42—C52—H52C109.5
C92—C82—H82115.4H52A—C52—H52B109.5
C72—C82—H82115.4H52A—C52—H52C109.5
O21—C11—O11125.5 (9)H52B—C52—H52C109.5
O21—C11—C21124.0 (9)
O31—C71—C81—C91179.6 (12)C93—C83—C73—O4313.9 (19)
O42—C72—C82—C923.8 (19)C12—C22—C32—C42176.7 (9)
O22—C12—C22—N215.7 (13)C22—C32—C42—C6269.5 (13)
O22—C12—C22—C32139.7 (10)C22—C32—C42—C52168.2 (9)
N2—C22—C32—C4263.3 (12)C83—C93—C103—O53175.8 (11)
O12—C12—C22—N2165.2 (8)C83—C93—C103—O637.2 (18)
O12—C12—C22—C3241.2 (12)C81—C91—C101—O51180.0 (12)
N3—C23—C33—C4364.8 (12)C81—C91—C101—O611 (2)
O13—C13—C23—N3175.0 (8)C103—C93—C83—C732 (2)
O13—C13—C23—C3354.2 (11)C13—C23—C33—C43177.3 (9)
O32—C72—C82—C92175.6 (11)C82—C92—C102—O52178.7 (12)
O41—C71—C81—C911 (2)C82—C92—C102—O621 (2)
O23—C13—C23—N36.7 (14)C11—C21—C31—C4171.7 (12)
O23—C13—C23—C33127.5 (11)C61—C41—C31—C21173.5 (10)
C102—C92—C82—C720 (2)C63—C43—C33—C2370.7 (13)
N1—C21—C11—O2124.2 (13)C31—C21—C11—O2194.1 (12)
N1—C21—C11—O11156.4 (8)C31—C21—C11—O1185.3 (11)
N1—C21—C31—C41172.0 (9)C51—C41—C31—C2158.9 (15)
C101—C91—C81—C711 (2)C53—C43—C33—C23166.5 (9)
C93—C83—C73—O33170.2 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O61—H61···O410.821.622.433 (8)171
N2—H2B···O23i0.892.032.860 (9)155
N2—H2C···O51ii0.891.922.780 (10)162
O12—H12···O33iii0.821.782.592 (10)172
O62—H62···O420.821.672.454 (9)159
O63—H63···O430.821.632.449 (10)176
N3—H3A···O22iv0.891.992.786 (9)148
N3—H3B···O53v0.891.952.829 (10)168
N3—H3C···O63vi0.892.002.866 (10)165
O13—H13···O52vii0.821.802.589 (10)161
O11—H11···O310.821.802.599 (9)163
N1—H1A···O21viii0.892.182.890 (9)137
N1—H1B···O42iv0.891.982.863 (9)170
N1—H1C···O32vii0.891.992.867 (10)171
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1, y1, z+1; (iii) x+1, y+1, z+1; (iv) x+1/2, y1/2, z; (v) x+1/2, y1/2, z+1; (vi) x+1/2, y+1/2, z+1; (vii) x+1/2, y+1/2, z; (viii) x+3/2, y1/2, z+1.
(II) L-Lisinium hydrogen maleate hemihydrate top
Crystal data top
C6H14NO2+·C4H3O4·0.5H2OF(000) = 548
Mr = 256.26Dx = 1.280 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.5217 (9) ÅCell parameters from 3141 reflections
b = 5.9974 (3) Åθ = 1.8–28.1°
c = 19.3426 (12) ŵ = 0.11 mm1
β = 95.848 (6)°T = 298 K
V = 1329.62 (15) Å3Needle, clear light colourless
Z = 40.25 × 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 Source3452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.8°
ω scansh = 1414
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 77
Tmin = 0.949, Tmax = 1.000l = 2424
17017 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.064H-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 reflectionsΔρmax = 0.15 e Å3
329 parametersΔρmin = 0.14 e Å3
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
xyzUiso*/Ueq
O10.2729 (3)0.3576 (6)0.55993 (14)0.0558 (9)
H10.29650.23920.57730.084*
O520.6863 (3)0.4547 (6)0.39132 (15)0.0615 (10)
O20.2448 (4)0.1518 (7)0.46452 (18)0.0822 (13)
O620.5944 (3)0.6140 (6)0.29963 (17)0.0595 (10)
H620.55430.57710.26400.089*
O420.4728 (3)0.4996 (6)0.19698 (16)0.0658 (11)
O320.4175 (3)0.1871 (6)0.14387 (14)0.0627 (10)
N10.1596 (3)0.7067 (6)0.50321 (16)0.0438 (10)
H1A0.12150.81520.47910.053*
H1B0.22270.76290.52750.053*
H1C0.11330.64580.53210.053*
C10.2393 (4)0.3277 (9)0.4933 (2)0.0469 (12)
C20.1956 (4)0.5335 (8)0.4547 (2)0.0412 (12)
H20.12530.49010.42490.049*
C1020.6266 (4)0.4406 (9)0.3344 (2)0.0456 (12)
C30.2810 (4)0.6275 (9)0.4072 (2)0.0544 (14)
H30.24620.76420.38650.065*
C920.5923 (4)0.2154 (9)0.3099 (2)0.0481 (13)
H920.61990.09970.33910.058*
C820.5268 (4)0.1513 (9)0.2514 (2)0.0509 (13)
H820.51630.00180.24640.061*
C720.4687 (4)0.2892 (9)0.1939 (2)0.0481 (13)
C40.3980 (4)0.6926 (11)0.4465 (3)0.0767 (18)
H4A0.43810.56070.46400.115*
H4B0.38470.78880.48460.115*
H4C0.44470.76900.41560.115*
C50.3014 (5)0.4712 (12)0.3475 (3)0.0799 (19)
H5A0.35260.54560.31800.096*
H5B0.34230.34040.36680.096*
C60.1947 (6)0.3948 (17)0.3028 (3)0.130 (4)
H6A0.21740.30050.26640.196*
H6B0.15350.52210.28270.196*
H6C0.14500.31310.33060.196*
O50.0101 (3)0.4666 (6)0.58072 (14)0.0604 (10)
O60.0433 (4)0.1552 (7)0.63896 (16)0.0750 (12)
H60.07320.11470.67720.113*
O1W10.4655 (3)0.3364 (7)0.90954 (13)0.0605 (10)
H1WA0.50880.41230.88540.091*
H1WB0.41980.25550.88280.091*
O30.2264 (3)0.1948 (7)0.84460 (15)0.0716 (12)
O40.1333 (3)0.0388 (6)0.75155 (16)0.0704 (12)
O120.1953 (3)0.8213 (7)0.09220 (17)0.0786 (12)
H120.20890.93630.11290.118*
N20.3793 (3)0.4947 (7)0.02938 (17)0.0460 (10)
H2A0.36840.39050.06080.055*
H2B0.41330.61310.05050.055*
H2C0.42470.44090.00120.055*
O220.3705 (3)0.8829 (8)0.03935 (19)0.0900 (15)
C120.2850 (4)0.7722 (10)0.0474 (2)0.0507 (13)
C70.1728 (4)0.2076 (10)0.7847 (2)0.0549 (14)
C220.2642 (4)0.5613 (9)0.0074 (2)0.0480 (13)
H220.24000.44440.04130.058*
C90.1072 (4)0.4986 (9)0.6932 (2)0.0532 (14)
H90.10730.65180.68580.064*
C320.1690 (4)0.5858 (10)0.0408 (3)0.0597 (15)
H320.10070.64760.01300.072*
C100.0504 (4)0.3657 (10)0.6344 (2)0.0513 (14)
C520.2014 (5)0.7500 (11)0.1001 (3)0.0708 (16)
H52A0.26200.68370.13210.085*
H52B0.23370.88340.08100.085*
C80.1579 (4)0.4335 (10)0.7550 (2)0.0563 (14)
H80.18860.54800.78370.068*
C620.1007 (6)0.8169 (14)0.1402 (3)0.109 (3)
H62A0.12890.91080.17850.163*
H62B0.06560.68570.15760.163*
H62C0.04360.89660.11010.163*
C420.1327 (5)0.3614 (10)0.0677 (3)0.0814 (19)
H42A0.19560.30030.09830.122*
H42B0.11430.26180.02920.122*
H42C0.06540.38000.09250.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.074 (2)0.038 (2)0.0506 (17)0.0084 (18)0.0163 (16)0.0056 (17)
O520.077 (2)0.050 (3)0.0506 (18)0.003 (2)0.0233 (17)0.0063 (19)
O20.142 (4)0.036 (3)0.063 (2)0.008 (2)0.020 (2)0.003 (2)
O620.082 (3)0.038 (2)0.055 (2)0.0075 (19)0.0090 (19)0.0017 (18)
O420.107 (3)0.041 (3)0.046 (2)0.013 (2)0.0121 (18)0.0069 (18)
O320.076 (2)0.064 (3)0.0424 (17)0.006 (2)0.0201 (17)0.0056 (19)
N10.045 (2)0.037 (3)0.048 (2)0.0046 (19)0.0013 (18)0.010 (2)
C10.052 (3)0.039 (3)0.047 (3)0.003 (2)0.007 (2)0.001 (3)
C20.046 (3)0.035 (3)0.041 (2)0.003 (2)0.004 (2)0.003 (2)
C1020.051 (3)0.040 (3)0.045 (3)0.002 (3)0.000 (2)0.002 (3)
C30.055 (3)0.055 (4)0.054 (3)0.007 (3)0.012 (3)0.007 (3)
C920.062 (3)0.037 (3)0.043 (3)0.005 (3)0.010 (2)0.001 (2)
C820.066 (3)0.036 (3)0.047 (3)0.001 (3)0.013 (2)0.000 (2)
C720.053 (3)0.053 (4)0.036 (3)0.010 (3)0.003 (2)0.001 (3)
C40.056 (4)0.077 (5)0.100 (4)0.010 (3)0.020 (3)0.002 (4)
C50.079 (4)0.092 (5)0.071 (3)0.001 (4)0.022 (3)0.008 (4)
C60.111 (6)0.208 (11)0.070 (4)0.006 (6)0.000 (4)0.052 (6)
O50.060 (2)0.076 (3)0.0413 (16)0.023 (2)0.0131 (15)0.016 (2)
O60.100 (3)0.065 (3)0.052 (2)0.032 (2)0.031 (2)0.007 (2)
O1W10.074 (3)0.062 (3)0.0430 (16)0.009 (2)0.0062 (17)0.0055 (19)
O30.092 (3)0.072 (3)0.0446 (18)0.008 (2)0.0236 (18)0.013 (2)
O40.101 (3)0.044 (3)0.059 (2)0.017 (2)0.025 (2)0.0058 (19)
O120.076 (3)0.081 (3)0.070 (2)0.013 (2)0.031 (2)0.027 (2)
N20.045 (2)0.049 (3)0.0442 (19)0.005 (2)0.0015 (17)0.004 (2)
O220.058 (3)0.102 (4)0.102 (3)0.026 (2)0.027 (2)0.058 (3)
C120.045 (3)0.060 (4)0.045 (3)0.007 (3)0.003 (2)0.007 (3)
C70.059 (3)0.059 (4)0.044 (3)0.007 (3)0.005 (2)0.008 (3)
C220.045 (3)0.051 (4)0.046 (3)0.004 (2)0.010 (2)0.007 (2)
C90.071 (4)0.041 (3)0.044 (2)0.010 (3)0.012 (2)0.001 (3)
C320.041 (3)0.066 (4)0.071 (3)0.001 (3)0.000 (3)0.024 (3)
C100.048 (3)0.060 (4)0.046 (3)0.019 (3)0.003 (2)0.001 (3)
C520.067 (4)0.067 (4)0.081 (4)0.012 (3)0.021 (3)0.004 (3)
C80.072 (4)0.048 (3)0.046 (3)0.014 (3)0.012 (2)0.002 (3)
C620.115 (6)0.104 (6)0.118 (5)0.028 (5)0.066 (5)0.019 (5)
C420.066 (4)0.072 (5)0.105 (4)0.016 (3)0.003 (3)0.031 (4)
Geometric parameters (Å, º) top
O1—H10.8200O6—H60.8200
O1—C11.319 (5)O6—C101.269 (6)
O52—C1021.240 (5)O1W1—H1WA0.8499
O2—C11.198 (6)O1W1—H1WB0.8505
O62—H620.8200O3—C71.257 (5)
O62—C1021.273 (5)O4—C71.259 (6)
O42—C721.264 (6)O12—H120.8200
O32—C721.242 (5)O12—C121.313 (5)
N1—H1A0.8900N2—H2A0.8900
N1—H1B0.8900N2—H2B0.8900
N1—H1C0.8900N2—H2C0.8900
N1—C21.488 (5)N2—C221.494 (5)
C1—C21.503 (7)O22—C121.185 (5)
C2—H20.9800C12—C221.514 (7)
C2—C31.522 (6)C7—C81.475 (7)
C102—C921.472 (7)C22—H220.9800
C3—H30.9800C22—C321.518 (6)
C3—C41.529 (6)C9—H90.9300
C3—C51.524 (7)C9—C101.485 (6)
C92—H920.9300C9—C81.334 (6)
C92—C821.349 (5)C32—H320.9800
C82—H820.9300C32—C521.529 (7)
C82—C721.490 (6)C32—C421.517 (7)
C4—H4A0.9600C52—H52A0.9700
C4—H4B0.9600C52—H52B0.9700
C4—H4C0.9600C52—C621.515 (7)
C5—H5A0.9700C8—H80.9300
C5—H5B0.9700C62—H62A0.9600
C5—C61.501 (8)C62—H62B0.9600
C6—H6A0.9600C62—H62C0.9600
C6—H6B0.9600C42—H42A0.9600
C6—H6C0.9600C42—H42B0.9600
O5—C101.249 (5)C42—H42C0.9600
C1—O1—H1109.5H1WA—O1W1—H1WB109.5
C102—O62—H62109.5C12—O12—H12109.5
H1A—N1—H1B109.5H2A—N2—H2B109.5
H1A—N1—H1C109.5H2A—N2—H2C109.5
H1B—N1—H1C109.5H2B—N2—H2C109.5
C2—N1—H1A109.5C22—N2—H2A109.5
C2—N1—H1B109.5C22—N2—H2B109.5
C2—N1—H1C109.5C22—N2—H2C109.5
O1—C1—C2115.1 (4)O12—C12—C22111.7 (4)
O2—C1—O1123.4 (5)O22—C12—O12123.3 (5)
O2—C1—C2121.5 (4)O22—C12—C22125.0 (4)
N1—C2—C1111.1 (3)O3—C7—O4122.6 (5)
N1—C2—H2106.9O3—C7—C8116.2 (5)
N1—C2—C3111.2 (4)O4—C7—C8121.2 (4)
C1—C2—H2106.9N2—C22—C12106.7 (4)
C1—C2—C3113.6 (4)N2—C22—H22107.8
C3—C2—H2106.9N2—C22—C32113.3 (4)
O52—C102—O62121.3 (5)C12—C22—H22107.8
O52—C102—C92117.1 (4)C12—C22—C32113.3 (4)
O62—C102—C92121.6 (4)C32—C22—H22107.8
C2—C3—H3107.1C10—C9—H9114.8
C2—C3—C4112.7 (4)C8—C9—H9114.8
C2—C3—C5112.8 (5)C8—C9—C10130.4 (5)
C4—C3—H3107.1C22—C32—H32106.8
C5—C3—H3107.1C22—C32—C52112.7 (4)
C5—C3—C4109.7 (4)C52—C32—H32106.8
C102—C92—H92115.1C42—C32—C22111.5 (5)
C82—C92—C102129.8 (5)C42—C32—H32106.8
C82—C92—H92115.1C42—C32—C52111.7 (4)
C92—C82—H82115.2O5—C10—O6121.3 (5)
C92—C82—C72129.7 (5)O5—C10—C9118.3 (5)
C72—C82—H82115.2O6—C10—C9120.4 (5)
O42—C72—C82120.5 (4)C32—C52—H52A108.7
O32—C72—O42122.8 (5)C32—C52—H52B108.7
O32—C72—C82116.8 (5)H52A—C52—H52B107.6
C3—C4—H4A109.5C62—C52—C32114.4 (5)
C3—C4—H4B109.5C62—C52—H52A108.7
C3—C4—H4C109.5C62—C52—H52B108.7
H4A—C4—H4B109.5C7—C8—H8115.1
H4A—C4—H4C109.5C9—C8—C7129.9 (5)
H4B—C4—H4C109.5C9—C8—H8115.1
C3—C5—H5A108.2C52—C62—H62A109.5
C3—C5—H5B108.2C52—C62—H62B109.5
H5A—C5—H5B107.4C52—C62—H62C109.5
C6—C5—C3116.3 (5)H62A—C62—H62B109.5
C6—C5—H5A108.2H62A—C62—H62C109.5
C6—C5—H5B108.2H62B—C62—H62C109.5
C5—C6—H6A109.5C32—C42—H42A109.5
C5—C6—H6B109.5C32—C42—H42B109.5
C5—C6—H6C109.5C32—C42—H42C109.5
H6A—C6—H6B109.5H42A—C42—H42B109.5
H6A—C6—H6C109.5H42A—C42—H42C109.5
H6B—C6—H6C109.5H42B—C42—H42C109.5
C10—O6—H6109.5
O1—C1—C2—N120.4 (6)O3—C7—C8—C9179.0 (5)
O1—C1—C2—C3105.8 (5)O4—C7—C8—C91.3 (9)
O52—C102—C92—C82178.8 (5)O12—C12—C22—N2167.6 (4)
O2—C1—C2—N1161.0 (5)O12—C12—C22—C3267.1 (5)
O2—C1—C2—C372.8 (6)N2—C22—C32—C5255.9 (6)
O62—C102—C92—C820.2 (8)N2—C22—C32—C4270.7 (6)
N1—C2—C3—C466.5 (5)O22—C12—C22—N213.3 (7)
N1—C2—C3—C5168.6 (4)O22—C12—C22—C32112.0 (6)
C1—C2—C3—C459.7 (6)C12—C22—C32—C5265.8 (5)
C1—C2—C3—C565.3 (5)C12—C22—C32—C42167.6 (4)
C2—C3—C5—C654.5 (8)C22—C32—C52—C62167.7 (5)
C102—C92—C82—C720.2 (9)C10—C9—C8—C70.6 (10)
C92—C82—C72—O423.2 (8)C8—C9—C10—O5179.0 (5)
C92—C82—C72—O32176.7 (5)C8—C9—C10—O61.1 (9)
C4—C3—C5—C6178.9 (6)C42—C32—C52—C6265.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O52i0.821.822.619 (5)166
O62—H62···O420.821.592.410 (5)177
N1—H1A···O5ii0.892.032.871 (5)158
N1—H1C···O50.891.922.796 (5)168
O6—H6···O40.821.602.418 (4)179
O1W1—H1WA···O32iii0.851.962.756 (5)155
O12—H12···O3iv0.821.782.594 (5)175
N2—H2A···O320.892.052.881 (5)155
N2—H2B···O1W1iii0.892.032.892 (6)163
N2—H2C···O1W1v0.891.942.780 (5)157
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x, y+1/2, z+1; (iii) x+1, y+1/2, z+1; (iv) x, y+1, z1; (v) x, y, z1.
(III) L-Norvalinium hydrogen maleate–L-norvaline (1/1) top
Crystal data top
C5H11NO2+·C4H3O4·C5H12NO2F(000) = 376
Mr = 350.37Dx = 1.260 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 12.2269 (6) ÅCell parameters from 2037 reflections
b = 5.30779 (17) Åθ = 1.8–28.2°
c = 15.4678 (6) ŵ = 0.10 mm1
β = 113.055 (5)°T = 298 K
V = 923.65 (7) Å3Plate, clear light colourless
Z = 20.5 × 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 Source2642 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 10.3457 pixels mm-1θmax = 26.4°, θmin = 1.8°
ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 65
Tmin = 0.900, Tmax = 1.000l = 1919
5895 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.29 e Å3
262 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/UeqOcc. (<1)
N20.5847 (2)0.1724 (5)0.80036 (16)0.0383 (6)
H2A0.59590.30440.76930.046*
H2B0.51110.17630.79870.046*
H2C0.59520.03090.77370.046*
O20.37615 (18)0.2209 (4)0.83252 (15)0.0415 (5)
O50.5965 (2)0.6802 (5)0.70792 (15)0.0545 (7)
O210.59257 (19)0.5987 (4)0.89350 (15)0.0428 (6)
O110.7387 (2)0.4643 (5)1.02484 (14)0.0477 (6)
O10.2532 (2)0.3646 (5)0.89580 (16)0.0475 (6)
H10.26850.22970.92390.071*
N10.3696 (2)0.6466 (5)0.73896 (17)0.0377 (6)
H1A0.34950.52040.69780.045*
H1B0.44590.63230.77700.045*
H1C0.35800.79260.70840.045*
O30.6529 (2)0.6476 (6)0.36432 (15)0.0588 (7)
C110.6641 (3)0.4389 (6)0.9399 (2)0.0335 (7)
O60.6659 (4)0.9279 (5)0.6289 (2)0.0856 (11)
H60.67980.92260.58120.128*
C90.6295 (3)0.7140 (7)0.6429 (2)0.0441 (8)
O40.6878 (3)0.9153 (6)0.4798 (2)0.0804 (10)
C210.6714 (3)0.1820 (6)0.8997 (2)0.0363 (7)
H210.64620.05710.93480.044*
C10.3117 (3)0.3830 (6)0.8442 (2)0.0322 (6)
C80.6291 (4)0.5024 (7)0.5828 (3)0.0594 (11)
H80.61750.34620.60510.071*
C60.6611 (3)0.6944 (7)0.4442 (2)0.0439 (8)
C70.6423 (4)0.4942 (7)0.5016 (3)0.0576 (10)
H70.63910.33310.47710.069*
C20.2950 (3)0.6375 (6)0.7955 (2)0.0370 (7)
H20.32530.76630.84460.044*
C30.1667 (3)0.7012 (9)0.7366 (3)0.0658 (11)
H3AA0.12390.71060.77770.079*0.901 (9)
H3AB0.16400.86720.70960.079*0.901 (9)
H3BC0.13110.53610.71830.079*0.099 (9)
H3BD0.13810.76000.78330.079*0.099 (9)
C40.1047 (4)0.5257 (14)0.6609 (4)0.086 (2)0.901 (9)
H4A0.10880.35800.68690.103*0.901 (9)
H4B0.14430.52160.61740.103*0.901 (9)
C50.0261 (6)0.598 (2)0.6071 (6)0.160 (5)0.901 (9)
H5A0.06270.48000.55690.239*0.901 (9)
H5B0.03070.76420.58170.239*0.901 (9)
H5C0.06660.59380.64910.239*0.901 (9)
C4B0.106 (4)0.837 (10)0.664 (4)0.078 (7)0.099 (9)
H4BA0.13740.79540.61720.094*0.099 (9)
H4BB0.13111.00960.68310.094*0.099 (9)
C5B0.025 (4)0.850 (12)0.613 (4)0.086 (10)0.099 (9)
H5BA0.05150.71000.56990.130*0.099 (9)
H5BB0.04651.00450.57800.130*0.099 (9)
H5BC0.06300.84200.65660.130*0.099 (9)
C310.7941 (3)0.1072 (8)0.9071 (2)0.0528 (9)
H31A0.84650.10070.97310.063*0.954 (7)
H31B0.78990.06140.88190.063*0.954 (7)
H31C0.83780.26300.92880.063*0.046 (7)
H31D0.82030.00050.96220.063*0.046 (7)
C410.8479 (4)0.2757 (10)0.8583 (3)0.0665 (14)0.954 (7)
H41A0.85740.44270.88580.080*0.954 (7)
H41B0.79470.28910.79270.080*0.954 (7)
C510.9687 (5)0.1791 (18)0.8650 (5)0.124 (3)0.954 (7)
H51A1.01720.13940.92930.186*0.954 (7)
H51B1.00700.30660.84290.186*0.954 (7)
H51C0.95760.03050.82720.186*0.954 (7)
C4B10.851 (7)0.008 (17)0.859 (6)0.049 (6)0.046 (7)
H4BC0.79860.06180.79620.059*0.046 (7)
H4BD0.83010.16780.86100.059*0.046 (7)
C5B10.956 (6)0.026 (17)0.843 (7)0.047 (11)0.046 (7)
H5BD0.94060.13430.78950.071*0.046 (7)
H5BE0.98390.13440.83070.071*0.046 (7)
H5BF1.01630.10110.89720.071*0.046 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0404 (13)0.0370 (15)0.0414 (13)0.0062 (12)0.0203 (11)0.0116 (14)
O20.0490 (12)0.0336 (12)0.0503 (13)0.0039 (11)0.0284 (10)0.0039 (12)
O50.0732 (16)0.0565 (17)0.0429 (12)0.0016 (14)0.0326 (12)0.0022 (14)
O210.0496 (12)0.0336 (13)0.0406 (11)0.0005 (10)0.0125 (10)0.0051 (11)
O110.0598 (14)0.0464 (15)0.0304 (11)0.0070 (12)0.0107 (10)0.0059 (12)
O10.0649 (15)0.0398 (14)0.0538 (14)0.0116 (12)0.0406 (13)0.0154 (12)
N10.0420 (13)0.0356 (15)0.0378 (13)0.0023 (12)0.0183 (11)0.0074 (13)
O30.0774 (16)0.068 (2)0.0360 (12)0.0014 (16)0.0282 (11)0.0020 (15)
C110.0415 (16)0.0308 (17)0.0322 (15)0.0017 (14)0.0187 (14)0.0006 (15)
O60.176 (3)0.0359 (16)0.073 (2)0.016 (2)0.079 (2)0.0111 (16)
C90.059 (2)0.0364 (19)0.0395 (17)0.0081 (17)0.0220 (15)0.0016 (17)
O40.153 (3)0.0392 (16)0.0747 (19)0.0067 (18)0.072 (2)0.0028 (16)
C210.0451 (16)0.0324 (17)0.0333 (15)0.0003 (14)0.0175 (13)0.0007 (15)
C10.0349 (15)0.0327 (17)0.0294 (14)0.0002 (13)0.0132 (12)0.0018 (14)
C80.108 (3)0.0307 (19)0.055 (2)0.001 (2)0.048 (2)0.0042 (18)
C60.0545 (19)0.041 (2)0.0397 (17)0.0033 (17)0.0217 (15)0.0010 (17)
C70.102 (3)0.0314 (19)0.054 (2)0.002 (2)0.046 (2)0.0048 (18)
C20.0485 (16)0.0326 (17)0.0365 (15)0.0065 (14)0.0235 (13)0.0067 (15)
C30.061 (2)0.069 (3)0.074 (2)0.021 (2)0.033 (2)0.033 (3)
C40.051 (3)0.114 (5)0.078 (3)0.006 (3)0.009 (2)0.001 (4)
C50.059 (4)0.244 (13)0.129 (6)0.017 (6)0.013 (4)0.003 (8)
C4B0.061 (10)0.072 (12)0.088 (11)0.016 (10)0.014 (9)0.039 (10)
C5B0.065 (13)0.079 (16)0.095 (16)0.014 (14)0.008 (12)0.037 (14)
C310.0509 (19)0.051 (2)0.0521 (19)0.0119 (18)0.0161 (16)0.0088 (19)
C410.050 (2)0.079 (4)0.076 (3)0.001 (2)0.030 (2)0.000 (3)
C510.059 (3)0.178 (9)0.151 (6)0.009 (5)0.058 (4)0.003 (7)
C4B10.048 (10)0.048 (12)0.053 (11)0.006 (11)0.021 (9)0.011 (11)
C5B10.034 (19)0.04 (2)0.07 (2)0.027 (19)0.024 (16)0.01 (2)
Geometric parameters (Å, º) top
N2—H2A0.8900C3—C41.456 (7)
N2—H2B0.8900C3—C4B1.29 (4)
N2—H2C0.8900C4—H4A0.9700
N2—C211.487 (4)C4—H4B0.9700
O2—C11.227 (4)C4—C51.533 (8)
O5—C91.234 (4)C5—H5A0.9600
O21—C111.228 (4)C5—H5B0.9600
O11—C111.279 (4)C5—H5C0.9600
O1—H10.8200C4B—H4BA0.9700
O1—C11.268 (3)C4B—H4BB0.9700
N1—H1A0.8900C4B—C5B1.49 (6)
N1—H1B0.8900C5B—H5BA0.9600
N1—H1C0.8900C5B—H5BB0.9600
N1—C21.491 (3)C5B—H5BC0.9600
O3—C61.226 (4)C31—H31A0.9700
C11—C211.516 (4)C31—H31B0.9700
O6—H60.8200C31—H31C0.9700
O6—C91.269 (4)C31—H31D0.9700
C9—C81.457 (5)C31—C411.480 (6)
O4—C61.282 (5)C31—C4B11.32 (7)
C21—H210.9800C41—H41A0.9700
C21—C311.512 (4)C41—H41B0.9700
C1—C21.521 (4)C41—C511.528 (6)
C8—H80.9300C51—H51A0.9600
C8—C71.329 (5)C51—H51B0.9600
C6—C71.459 (5)C51—H51C0.9600
C7—H70.9300C4B1—H4BC0.9700
C2—H20.9800C4B1—H4BD0.9700
C2—C31.512 (5)C4B1—C5B11.41 (10)
C3—H3AA0.9700C5B1—H5BD0.9600
C3—H3AB0.9700C5B1—H5BE0.9600
C3—H3BC0.9700C5B1—H5BF0.9600
C3—H3BD0.9700
H2A—N2—H2B109.5C3—C4—C5112.4 (6)
H2A—N2—H2C109.5H4A—C4—H4B107.9
H2B—N2—H2C109.5C5—C4—H4A109.1
C21—N2—H2A109.5C5—C4—H4B109.1
C21—N2—H2B109.5C4—C5—H5A109.5
C21—N2—H2C109.5C4—C5—H5B109.5
C1—O1—H1109.5C4—C5—H5C109.5
H1A—N1—H1B109.5H5A—C5—H5B109.5
H1A—N1—H1C109.5H5A—C5—H5C109.5
H1B—N1—H1C109.5H5B—C5—H5C109.5
C2—N1—H1A109.5C3—C4B—H4BA105.3
C2—N1—H1B109.5C3—C4B—H4BB105.3
C2—N1—H1C109.5C3—C4B—C5B128 (4)
O21—C11—O11125.9 (3)H4BA—C4B—H4BB106.0
O21—C11—C21121.6 (3)C5B—C4B—H4BA105.3
O11—C11—C21112.5 (3)C5B—C4B—H4BB105.3
C9—O6—H6109.5C4B—C5B—H5BA109.5
O5—C9—O6121.2 (3)C4B—C5B—H5BB109.5
O5—C9—C8119.2 (3)C4B—C5B—H5BC109.5
O6—C9—C8119.6 (3)H5BA—C5B—H5BB109.5
N2—C21—C11108.8 (3)H5BA—C5B—H5BC109.5
N2—C21—H21107.4H5BB—C5B—H5BC109.5
N2—C21—C31110.8 (2)C21—C31—H31A108.4
C11—C21—H21107.4C21—C31—H31B108.4
C31—C21—C11114.9 (3)C21—C31—H31C101.4
C31—C21—H21107.4C21—C31—H31D101.4
O2—C1—O1126.3 (3)H31A—C31—H31B107.5
O2—C1—C2121.3 (2)H31C—C31—H31D104.6
O1—C1—C2112.4 (3)C41—C31—C21115.3 (3)
C9—C8—H8114.4C41—C31—H31A108.4
C7—C8—C9131.1 (4)C41—C31—H31B108.4
C7—C8—H8114.4C4B1—C31—C21142 (4)
O3—C6—O4121.6 (4)C4B1—C31—H31C101.4
O3—C6—C7119.7 (4)C4B1—C31—H31D101.4
O4—C6—C7118.7 (3)C31—C41—H41A109.2
C8—C7—C6131.1 (4)C31—C41—H41B109.2
C8—C7—H7114.4C31—C41—C51111.9 (5)
C6—C7—H7114.4H41A—C41—H41B107.9
N1—C2—C1108.9 (2)C51—C41—H41A109.2
N1—C2—H2107.4C51—C41—H41B109.2
N1—C2—C3111.6 (3)C41—C51—H51A109.5
C1—C2—H2107.4C41—C51—H51B109.5
C3—C2—C1113.8 (3)C41—C51—H51C109.5
C3—C2—H2107.4H51A—C51—H51B109.5
C2—C3—H3AA108.4H51A—C51—H51C109.5
C2—C3—H3AB108.4H51B—C51—H51C109.5
C2—C3—H3BC102.4C31—C4B1—H4BC99.1
C2—C3—H3BD102.4C31—C4B1—H4BD99.1
H3AA—C3—H3AB107.4C31—C4B1—C5B1150 (7)
H3BC—C3—H3BD104.9H4BC—C4B1—H4BD103.9
C4—C3—C2115.6 (4)C5B1—C4B1—H4BC99.1
C4—C3—H3AA108.4C5B1—C4B1—H4BD99.1
C4—C3—H3AB108.4C4B1—C5B1—H5BD109.5
C4B—C3—C2139 (2)C4B1—C5B1—H5BE109.5
C4B—C3—H3BC102.4C4B1—C5B1—H5BF109.5
C4B—C3—H3BD102.4H5BD—C5B1—H5BE109.5
C3—C4—H4A109.1H5BD—C5B1—H5BF109.5
C3—C4—H4B109.1H5BE—C5B1—H5BF109.5
N2—C21—C31—C4163.3 (4)O3—C6—C7—C8168.8 (5)
N2—C21—C31—C4B111 (7)C11—C21—C31—C4160.4 (4)
O2—C1—C2—N11.6 (4)C11—C21—C31—C4B1135 (7)
O2—C1—C2—C3123.7 (3)O6—C9—C8—C712.9 (7)
O5—C9—C8—C7168.5 (4)C9—C8—C7—C60.5 (8)
O21—C11—C21—N22.0 (4)O4—C6—C7—C812.2 (7)
O21—C11—C21—C31126.8 (3)C21—C31—C41—C51177.0 (4)
O11—C11—C21—N2178.2 (2)C21—C31—C4B1—C5B1156 (12)
O11—C11—C21—C3153.4 (4)C1—C2—C3—C459.6 (5)
O1—C1—C2—N1178.1 (3)C1—C2—C3—C4B154 (4)
O1—C1—C2—C356.7 (4)C2—C3—C4—C5177.7 (6)
N1—C2—C3—C464.2 (5)C2—C3—C4B—C5B173 (4)
N1—C2—C3—C4B30 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O20.891.932.794 (3)163
N2—H2C···O5i0.892.123.009 (4)172
O1—H1···O11ii0.821.642.437 (3)165
N1—H1B···O210.891.992.847 (3)161
O6—H6···O40.821.612.425 (4)172
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+2.
C22(12) motifs in different amino acid maleates (see also Fig. 1). The structures solved in this paper are highlighted in bold top
No.Maleate (M)CSD refcode (Groom & Allen, 2014)Comments related to C22(12) motif
1(GlyH)·M-RENBANAll 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-)2TENVOZThis 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-ETEYORThe 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-EDASUXThe 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-XADTOLThe 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-·H2OGIHGEK
15(DL-ArgH)·M-·
16(L-HisH)2·(M-)2TENVUF
17(L-HisH)·M-·H2OVAZJUD
18(L-HisH)2·(M-)2·3H2O
19(BetH)·M-NASQED01C22(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
22L-Met·L-MetH·M-**C33(17) is formed by L-Met···L-MetH (case 22) or L-Nva···L-NvaH (case 23) dications
23L-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.
 

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