X-ray studies of crystalline complexes involving amino acids and peptides. XLIV. Invariant features of supramolecular association and chiral effects in the complexes of arginine and lysine with tartaric acid

The tartaric acid complexes with arginine and lysine exhibit two stoichiometries depending upon the ionization state of the anion. The structures reported here are DL-argininium DL-hydrogen tartrate, bis(L-argininium) L-tartrate, bis(DL-lysinium) DL-tartrate monohydrate, L-lysinium D-hydrogen tartrate and L-lysinium L-hydrogen tartrate. During crystallization, L-lysine preferentially interacts with D-tartaric acid to form a complex when DL-tartaric acid is used in the experiment. The anions and the cations aggregate into separate alternating layers in four of the five complexes. In bis(L-argininium) L-tartrate, the amino acid layers are interconnected by individual tartrate ions which do not interact among themselves. The aggregation of argininium ions in the DL- and the L-arginine complexes is remarkably similar, which is in turn similar to those observed in other dicarboxylic acid complexes of arginine. Thus, argininium ions have a tendency to assume similar patterns of aggregation, which are largely unaffected by a change in the chemistry of partner molecules such as the introduction of hydroxyl groups or a change in chirality or stoichiometry. On the contrary, the lysinium ions exhibit fundamentally different aggregation patterns in the DL-DL complexes on the one hand and L-D and L-L complexes on the other. Interestingly, the pattern in the L-D complex is similar to that in the L-L complex. The lysinium ions in the DL-DL complex exhibit an aggregation pattern similar to those observed in the DL-lysine complexes involving other dicarboxylic acids. Thus, the effect of change in the chirality of a subset of the component complexes could be profound or marginal, in an unpredictable manner. The relevant crystal structures appear to indicate that the preference of L-lysine for D-tartaric acid is perhaps caused by chiral discrimination resulting from the amplification of a small energy difference.

Computing details

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

(I) DL-arginine DL-tartaric acid complex

Crystal data

C6H15N4O2^+·C4H5O6^−	Z = 2
Mr = 324.30	F(000) = 344
Triclinic, P1	Dx = 1.508 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4876 (16) Å	Cell parameters from 835 reflections
b = 10.021 (3) Å	θ = 1.6–22.0°
c = 13.868 (4) Å	µ = 0.13 mm^−1
α = 109.079 (5)°	T = 298 K
β = 94.378 (5)°	Plate, colourless
γ = 94.538 (5)°	0.25 × 0.2 × 0.1 mm
V = 714.3 (4) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	1543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 25.0°, θmin = 1.6°
ϕ and ω scan	h = −6→6
6914 measured reflections	k = −11→11
2504 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 0.0651P] where P = (Fo^2 + 2Fc^2)/3
2508 reflections	(Δ/σ)max < 0.001
260 parameters	Δρmax = 0.27 e Å^−3
52 restraints	Δρmin = −0.23 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.2455 (4)	0.5905 (3)	1.06068 (17)	0.0411 (7)
O2	−0.4559 (5)	0.7503 (3)	1.02198 (19)	0.0514 (8)
N1	−0.2269 (6)	0.4379 (3)	0.8647 (3)	0.0343 (8)
C1	−0.3313 (7)	0.6486 (4)	1.0000 (3)	0.0342 (9)
C2	−0.2778 (7)	0.5878 (3)	0.8884 (3)	0.0362 (9)
H2	−0.4174	0.5940	0.8422	0.043*
C3A	−0.0414 (7)	0.6684 (4)	0.8713 (3)	0.0310 (11)	0.824 (5)
H31	0.0862	0.6806	0.9268	0.037*	0.824 (5)
H32	0.0174	0.6140	0.8074	0.037*	0.824 (5)
C4A	−0.0980 (8)	0.8141 (4)	0.8672 (4)	0.0404 (12)	0.824 (5)
H41	−0.1745	0.8637	0.9276	0.048*	0.824 (5)
H42	−0.2126	0.8013	0.8072	0.048*	0.824 (5)
C3B	−0.191 (3)	0.7027 (16)	0.8434 (13)	0.036 (3)	0.176 (5)
H33	−0.3088	0.7718	0.8522	0.043*	0.176 (5)
H34	−0.1795	0.6595	0.7705	0.043*	0.176 (5)
C4B	0.062 (3)	0.7771 (14)	0.8984 (14)	0.043 (4)	0.176 (5)
H43	0.1838	0.7099	0.8835	0.051*	0.176 (5)
H44	0.0550	0.8111	0.9721	0.051*	0.176 (5)
C5	0.1386 (7)	0.9033 (4)	0.8623 (3)	0.0492 (11)
H5A	0.1056	1.0006	0.8734	0.059*
H5B	0.2625	0.9037	0.9161	0.059*
N6	0.2305 (6)	0.8457 (3)	0.7630 (2)	0.0409 (8)
C7	0.4125 (6)	0.9127 (3)	0.7339 (3)	0.0319 (8)
N8	0.5122 (6)	1.0401 (3)	0.7914 (3)	0.0436 (9)
N9	0.4972 (7)	0.8496 (4)	0.6445 (3)	0.0482 (10)
O11	−0.0430 (4)	0.1521 (3)	0.74693 (17)	0.0411 (7)
O12	−0.0821 (5)	0.0195 (2)	0.58267 (17)	0.0437 (7)
C13	0.0104 (6)	0.1294 (3)	0.6593 (3)	0.0285 (8)
C14	0.1883 (6)	0.2390 (3)	0.6389 (2)	0.0256 (8)
H14	0.3060	0.1896	0.5940	0.031*
O15	0.3187 (4)	0.3330 (2)	0.73050 (18)	0.0363 (6)
C16	0.0435 (6)	0.3222 (3)	0.5845 (2)	0.0300 (8)
H16	−0.0234	0.2584	0.5160	0.036*
O17	−0.1547 (5)	0.3708 (3)	0.6421 (2)	0.0421 (7)
C18	0.2080 (7)	0.4443 (4)	0.5737 (2)	0.0333 (9)
O19	0.1640 (5)	0.5675 (2)	0.60692 (18)	0.0459 (7)
O20	0.3959 (5)	0.4042 (2)	0.52453 (19)	0.0472 (7)
H1A	−0.055 (9)	0.431 (4)	0.902 (3)	0.074 (14)*
H1B	−0.220 (7)	0.399 (4)	0.803 (3)	0.050 (12)*
H1C	−0.365 (11)	0.387 (5)	0.892 (4)	0.118 (19)*
H6	0.168 (9)	0.766 (5)	0.724 (3)	0.078 (16)*
H8A	0.450 (7)	1.094 (4)	0.853 (3)	0.065 (13)*
H8B	0.651 (8)	1.080 (4)	0.774 (3)	0.057 (12)*
H9A	0.618 (7)	0.893 (4)	0.628 (3)	0.045 (12)*
H9B	0.445 (7)	0.758 (4)	0.611 (3)	0.054 (12)*
H12	0.0000	0.0000	0.5000	0.11 (2)*
H15	0.244 (9)	0.326 (5)	0.785 (3)	0.103 (19)*
H17	−0.278 (6)	0.380 (5)	0.609 (3)	0.078 (17)*
H20	0.5000	0.5000	0.5000	0.12 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0400 (16)	0.0502 (16)	0.0269 (14)	−0.0064 (12)	0.0063 (12)	0.0066 (12)
O2	0.0517 (18)	0.0457 (17)	0.0461 (17)	0.0105 (14)	0.0163 (14)	−0.0026 (13)
N1	0.034 (2)	0.0391 (19)	0.0218 (17)	−0.0022 (15)	0.0081 (16)	−0.0009 (15)
C1	0.032 (2)	0.033 (2)	0.029 (2)	−0.0128 (17)	0.0088 (17)	0.0003 (18)
C2	0.048 (2)	0.028 (2)	0.0281 (19)	−0.0039 (17)	0.0091 (17)	0.0045 (16)
C3A	0.032 (3)	0.033 (2)	0.030 (2)	0.007 (2)	0.014 (2)	0.0104 (19)
C4A	0.038 (3)	0.039 (3)	0.049 (3)	0.005 (2)	0.013 (2)	0.019 (2)
C3B	0.039 (6)	0.032 (6)	0.036 (6)	0.012 (6)	0.010 (6)	0.008 (5)
C4B	0.040 (6)	0.042 (6)	0.041 (6)	0.002 (6)	0.015 (6)	0.005 (6)
C5	0.058 (3)	0.037 (2)	0.046 (2)	−0.010 (2)	0.025 (2)	0.0034 (19)
N6	0.047 (2)	0.0312 (19)	0.0366 (19)	−0.0121 (16)	0.0156 (16)	0.0024 (16)
C7	0.034 (2)	0.027 (2)	0.032 (2)	0.0021 (16)	0.0062 (17)	0.0065 (16)
N8	0.044 (2)	0.0290 (18)	0.049 (2)	−0.0086 (16)	0.0234 (17)	0.0002 (16)
N9	0.062 (3)	0.033 (2)	0.041 (2)	−0.0107 (18)	0.0239 (18)	−0.0002 (17)
O11	0.0449 (16)	0.0461 (15)	0.0306 (14)	−0.0101 (12)	0.0141 (12)	0.0117 (12)
O12	0.0581 (18)	0.0310 (14)	0.0339 (15)	−0.0142 (12)	0.0142 (13)	0.0024 (12)
C13	0.0274 (19)	0.0270 (19)	0.033 (2)	0.0031 (15)	0.0082 (16)	0.0116 (16)
C14	0.0242 (18)	0.0266 (18)	0.0263 (18)	0.0008 (15)	0.0078 (15)	0.0087 (15)
O15	0.0351 (15)	0.0453 (15)	0.0236 (13)	−0.0118 (11)	−0.0019 (11)	0.0098 (12)
C16	0.033 (2)	0.032 (2)	0.0212 (17)	0.0000 (16)	0.0043 (15)	0.0039 (15)
O17	0.0283 (15)	0.0570 (18)	0.0421 (16)	0.0113 (13)	0.0048 (13)	0.0164 (13)
C18	0.050 (2)	0.026 (2)	0.0233 (18)	0.0014 (18)	0.0027 (17)	0.0080 (15)
O19	0.0632 (19)	0.0235 (15)	0.0461 (16)	0.0031 (13)	0.0116 (14)	0.0040 (12)
O20	0.0643 (19)	0.0348 (15)	0.0523 (16)	0.0094 (13)	0.0333 (15)	0.0210 (13)

Geometric parameters (Å, º)

O1—C1	1.254 (4)	C5—H5B	0.9700
O2—C1	1.240 (4)	N6—C7	1.320 (4)
N1—C2	1.483 (5)	N6—H6	0.84 (4)
N1—H1A	1.06 (5)	C7—N8	1.313 (4)
N1—H1B	0.82 (4)	C7—N9	1.332 (4)
N1—H1C	1.04 (6)	N8—H8A	0.96 (4)
C1—C2	1.527 (5)	N8—H8B	0.92 (4)
C2—C3B	1.540 (5)	N9—H9A	0.85 (4)
C2—C3A	1.549 (4)	N9—H9B	0.89 (4)
C2—H2	0.9800	O11—C13	1.224 (4)
C3A—C4A	1.534 (4)	O12—C13	1.290 (4)
C3A—H31	0.9700	O12—H12	1.225
C3A—H32	0.9700	C13—C14	1.522 (4)
C4A—C5	1.536 (4)	C14—O15	1.409 (4)
C4A—H41	0.9700	C14—C16	1.523 (5)
C4A—H42	0.9700	C14—H14	0.9800
C3B—C4B	1.540 (5)	O15—H15	0.91 (5)
C3B—H33	0.9700	C16—O17	1.422 (4)
C3B—H34	0.9700	C16—C18	1.517 (5)
C4B—C5	1.546 (5)	C16—H16	0.9800
C4B—H43	0.9700	O17—H17	0.82 (2)
C4B—H44	0.9700	C18—O19	1.219 (4)
C5—N6	1.454 (4)	C18—O20	1.298 (4)
C5—H5A	0.9700	O20—H20	1.233
C2—N1—H1A	111 (2)	N6—C5—C4A	110.6 (3)
C2—N1—H1B	111 (3)	N6—C5—C4B	107.6 (8)
H1A—N1—H1B	106 (3)	N6—C5—H5A	109.5
C2—N1—H1C	107 (3)	C4A—C5—H5A	109.5
H1A—N1—H1C	109 (3)	N6—C5—H5B	109.5
H1B—N1—H1C	112 (4)	C4A—C5—H5B	109.5
O2—C1—O1	126.1 (3)	C4B—C5—H5B	72.1
O2—C1—C2	117.1 (4)	H5A—C5—H5B	108.1
O1—C1—C2	116.8 (3)	C7—N6—C5	122.7 (3)
N1—C2—C1	109.9 (3)	C7—N6—H6	119 (3)
N1—C2—C3B	131.6 (8)	C5—N6—H6	118 (3)
C1—C2—C3B	113.3 (8)	N8—C7—N6	121.3 (3)
N1—C2—C3A	105.9 (3)	N8—C7—N9	119.3 (3)
C1—C2—C3A	110.3 (3)	N6—C7—N9	119.4 (3)
N1—C2—H2	110.2	C7—N8—H8A	123 (2)
C1—C2—H2	110.2	C7—N8—H8B	120 (2)
C3B—C2—H2	74.0	H8A—N8—H8B	117 (3)
C3A—C2—H2	110.2	C7—N9—H9A	118 (2)
C4A—C3A—C2	109.4 (3)	C7—N9—H9B	118 (2)
C4A—C3A—H31	109.8	H9A—N9—H9B	123 (3)
C2—C3A—H31	109.8	C13—O12—H12	118.3
C4A—C3A—H32	109.8	O11—C13—O12	123.4 (3)
C2—C3A—H32	109.8	O11—C13—C14	118.4 (3)
H31—C3A—H32	108.2	O12—C13—C14	118.2 (3)
C3A—C4A—C5	110.6 (3)	O15—C14—C13	111.6 (2)
C3A—C4A—H41	109.5	O15—C14—C16	109.7 (3)
C5—C4A—H41	109.5	C13—C14—C16	108.8 (3)
C3A—C4A—H42	109.5	O15—C14—H14	108.9
C5—C4A—H42	109.5	C13—C14—H14	108.9
H41—C4A—H42	108.1	C16—C14—H14	108.9
C2—C3B—C4B	109.5 (8)	C14—O15—H15	110 (3)
C2—C3B—H33	109.8	O17—C16—C18	111.7 (3)
C4B—C3B—H33	109.8	O17—C16—C14	107.7 (3)
C2—C3B—H34	109.8	C18—C16—C14	110.7 (3)
C4B—C3B—H34	109.8	O17—C16—H16	108.9
H33—C3B—H34	108.2	C18—C16—H16	108.9
C3B—C4B—C5	110.0 (8)	C14—C16—H16	108.9
C3B—C4B—H43	109.7	C16—O17—H17	115 (3)
C5—C4B—H43	109.7	O19—C18—O20	123.8 (3)
C3B—C4B—H44	109.7	O19—C18—C16	122.8 (3)
C5—C4B—H44	109.7	O20—C18—C16	113.4 (3)
H43—C4B—H44	108.2	C18—O20—H20	112.0
O2—C1—C2—N1	−155.9 (3)	C4B—C5—N6—C7	−145.1 (7)
O1—C1—C2—N1	24.0 (4)	C5—N6—C7—N8	−4.0 (6)
O2—C1—C2—C3B	46.6 (8)	C5—N6—C7—N9	175.9 (4)
O1—C1—C2—C3B	−133.6 (8)	O11—C13—C14—O15	16.5 (4)
O2—C1—C2—C3A	87.8 (4)	O12—C13—C14—O15	−165.6 (3)
O1—C1—C2—C3A	−92.4 (4)	O11—C13—C14—C16	−104.7 (3)
N1—C2—C3A—C4A	165.7 (3)	O12—C13—C14—C16	73.2 (4)
C1—C2—C3A—C4A	−75.5 (4)	O15—C14—C16—O17	−71.5 (3)
C2—C3A—C4A—C5	173.7 (3)	C13—C14—C16—O17	50.8 (3)
N1—C2—C3B—C4B	−84.8 (16)	O15—C14—C16—C18	50.9 (3)
C1—C2—C3B—C4B	66.5 (16)	C13—C14—C16—C18	173.3 (3)
C2—C3B—C4B—C5	−173.9 (11)	O17—C16—C18—O19	−3.3 (5)
C3A—C4A—C5—N6	70.5 (5)	C14—C16—C18—O19	−123.4 (3)
C3B—C4B—C5—N6	−79.1 (15)	O17—C16—C18—O20	177.8 (3)
C4A—C5—N6—C7	170.9 (4)	C14—C16—C18—O20	57.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	1.06 (5)	1.74 (5)	2.788 (4)	169 (3)
N1—H1B···O17	0.82 (4)	2.21 (4)	3.001 (4)	160 (3)
N1—H1C···O1^ii	1.04 (6)	2.29 (6)	3.171 (4)	141 (4)
N1—H1C···O2^ii	1.04 (6)	2.31 (6)	3.300 (4)	159 (4)
N6—H6···O19	0.84 (4)	2.11 (4)	2.892 (4)	155 (4)
N8—H8A···O2^iii	0.96 (4)	1.91 (4)	2.807 (4)	155 (3)
N8—H8B···O11^iv	0.92 (4)	1.89 (4)	2.801 (4)	174 (4)
N9—H9A···O12^iv	0.85 (4)	2.25 (4)	3.099 (4)	176 (3)
N9—H9B···O19	0.89 (4)	2.34 (4)	3.111 (5)	145 (3)
N9—H9B···O20^v	0.89 (4)	2.33 (4)	2.976 (4)	129 (3)
O12—H12···O12^vi	1.23	1.23	2.451 (4)	180
O15—H15···O1^i	0.91 (5)	2.02 (5)	2.813 (3)	144 (4)
O17—H17···O20^vii	0.82	2.13	2.953 (4)	178
O20—H20···O20^v	1.23	1.23	2.466 (4)	180

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x−1, −y+1, −z+2; (iii) −x, −y+2, −z+2; (iv) x+1, y+1, z; (v) −x+1, −y+1, −z+1; (vi) −x, −y, −z+1; (vii) x−1, y, z.

(II) L-arginine L-tartaric acid complex

Crystal data

2(C6H15N4O2)^+·C4H4O6^2^−	F(000) = 532
Mr = 498.51	Dx = 1.440 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1374 reflections
a = 9.907 (2) Å	θ = 1.5–25.0°
b = 8.7428 (18) Å	µ = 0.12 mm^−1
c = 14.076 (3) Å	T = 298 K
β = 109.412 (3)°	Plate, colourless
V = 1149.9 (4) Å^3	0.42 × 0.27 × 0.15 mm
Z = 2

Data collection

Bruker SMART CCD area detector diffractometer	2054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ϕ and ω scan	h = −11→11
8353 measured reflections	k = −10→9
2162 independent reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 0.2589P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2162 reflections	Δρmax = 0.37 e Å^−3
380 parameters	Δρmin = −0.17 e Å^−3
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (19)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6385 (2)	0.3214 (2)	0.80456 (14)	0.0372 (5)
O2	0.4988 (2)	0.5225 (3)	0.79604 (15)	0.0513 (6)
N1	0.5701 (2)	0.2930 (3)	0.60514 (16)	0.0281 (5)
C1	0.5556 (3)	0.4243 (3)	0.75787 (18)	0.0292 (5)
C2	0.5218 (3)	0.4347 (3)	0.64353 (18)	0.0272 (5)
H2	0.5767	0.5205	0.6304	0.033*
C3	0.3639 (3)	0.4659 (3)	0.58693 (18)	0.0319 (6)
H3A	0.3359	0.5594	0.6125	0.038*
H3B	0.3507	0.4814	0.5162	0.038*
C4	0.2674 (3)	0.3360 (4)	0.5972 (2)	0.0411 (7)
H4A	0.2712	0.2543	0.5515	0.049*
H4B	0.3043	0.2958	0.6652	0.049*
C5	0.1129 (3)	0.3821 (5)	0.5754 (2)	0.0437 (8)
H5A	0.0617	0.2990	0.5939	0.052*
H5B	0.1088	0.4703	0.6161	0.052*
N6	0.0434 (2)	0.4192 (3)	0.46961 (17)	0.0386 (6)
C7	−0.0955 (3)	0.4425 (4)	0.4291 (2)	0.0343 (6)
N8	−0.1806 (3)	0.4440 (4)	0.4843 (2)	0.0475 (7)
N9	−0.1526 (3)	0.4666 (4)	0.33043 (18)	0.0439 (7)
O11	0.8614 (2)	0.2550 (3)	0.69469 (15)	0.0465 (6)
O12	0.9239 (3)	0.4992 (3)	0.70440 (18)	0.0654 (8)
N11	0.9510 (3)	0.2266 (4)	0.89608 (18)	0.0351 (6)
C11	0.9236 (3)	0.3724 (4)	0.7406 (2)	0.0428 (8)
C12	1.0153 (3)	0.3497 (4)	0.8512 (2)	0.0377 (7)
H12	1.0222	0.4454	0.8888	0.045*
C13	1.1643 (3)	0.3000 (4)	0.8503 (2)	0.0413 (7)
H13A	1.1529	0.2096	0.8083	0.050*
H13B	1.2023	0.3806	0.8190	0.050*
C14	1.2733 (3)	0.2651 (4)	0.9523 (2)	0.0435 (7)
H14A	1.2378	0.1844	0.9851	0.052*
H14B	1.2901	0.3554	0.9946	0.052*
C15	1.4115 (3)	0.2148 (5)	0.9375 (2)	0.0497 (8)
H15A	1.3936	0.1272	0.8928	0.060*
H15B	1.4486	0.2971	0.9070	0.060*
N16	1.5155 (3)	0.1749 (4)	1.03412 (18)	0.0466 (7)
C17	1.6460 (3)	0.2285 (4)	1.0709 (2)	0.0359 (6)
N18	1.7052 (3)	0.3150 (4)	1.0187 (2)	0.0445 (7)
N19	1.7213 (3)	0.1958 (4)	1.1672 (2)	0.0529 (8)
O21	0.4623 (2)	0.0132 (3)	0.66299 (17)	0.0444 (5)
O22	0.5159 (2)	−0.2058 (3)	0.60332 (15)	0.0441 (5)
C23	0.5371 (3)	−0.1060 (3)	0.66868 (19)	0.0305 (6)
C24	0.6650 (3)	−0.1278 (3)	0.76652 (18)	0.0290 (6)
H24	0.6454	−0.2162	0.8027	0.035*
O25	0.6877 (2)	0.0017 (2)	0.83055 (14)	0.0365 (5)
C26	0.7999 (3)	−0.1605 (3)	0.74077 (18)	0.0302 (6)
H26	0.7883	−0.2606	0.7077	0.036*
O27	0.8179 (2)	−0.0494 (3)	0.67198 (14)	0.0387 (5)
C28	0.9295 (3)	−0.1695 (3)	0.83744 (19)	0.0322 (6)
O29	1.0307 (2)	−0.0753 (3)	0.84651 (17)	0.0479 (6)
O30	0.9270 (2)	−0.2697 (3)	0.89899 (14)	0.0436 (5)
H1A	0.527 (3)	0.211 (4)	0.619 (2)	0.028 (7)*
H1B	0.669 (4)	0.278 (5)	0.634 (2)	0.048 (9)*
H1C	0.545 (3)	0.298 (4)	0.537 (2)	0.035 (8)*
H6	0.101 (3)	0.418 (4)	0.432 (2)	0.042 (9)*
H8A	−0.148 (4)	0.445 (5)	0.546 (3)	0.045 (9)*
H8B	−0.269 (4)	0.445 (4)	0.454 (2)	0.032 (8)*
H9A	−0.100 (4)	0.458 (5)	0.293 (3)	0.060 (11)*
H9B	−0.246 (4)	0.480 (5)	0.309 (3)	0.058 (11)*
H11A	0.862 (4)	0.238 (5)	0.875 (3)	0.050 (10)*
H11B	0.988 (3)	0.217 (4)	0.966 (2)	0.043 (9)*
H11C	0.977 (4)	0.134 (5)	0.878 (3)	0.055 (11)*
H16	1.495 (3)	0.116 (4)	1.080 (2)	0.037 (8)*
H18A	1.670 (3)	0.326 (4)	0.952 (3)	0.045 (9)*
H18B	1.802 (4)	0.352 (5)	1.058 (3)	0.053 (10)*
H19A	1.676 (3)	0.141 (5)	1.202 (3)	0.049 (9)*
H19B	1.816 (5)	0.213 (6)	1.184 (3)	0.082 (14)*
H25	0.627 (3)	0.067 (4)	0.802 (2)	0.051 (11)*
H27	0.841 (4)	0.040 (6)	0.698 (3)	0.054 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0387 (10)	0.0469 (12)	0.0238 (9)	0.0092 (10)	0.0073 (8)	0.0036 (9)
O2	0.0635 (14)	0.0573 (15)	0.0324 (11)	0.0204 (12)	0.0149 (10)	−0.0043 (10)
N1	0.0258 (11)	0.0335 (13)	0.0228 (11)	0.0013 (10)	0.0054 (9)	0.0011 (10)
C1	0.0262 (11)	0.0341 (14)	0.0254 (12)	−0.0020 (12)	0.0061 (10)	−0.0014 (11)
C2	0.0262 (12)	0.0276 (13)	0.0260 (12)	−0.0007 (11)	0.0063 (10)	0.0016 (10)
C3	0.0306 (13)	0.0355 (15)	0.0260 (13)	0.0036 (12)	0.0046 (10)	0.0032 (11)
C4	0.0268 (14)	0.0496 (19)	0.0441 (17)	0.0047 (13)	0.0081 (12)	0.0134 (14)
C5	0.0268 (13)	0.069 (2)	0.0345 (15)	0.0055 (14)	0.0097 (11)	0.0151 (16)
N6	0.0248 (10)	0.0620 (17)	0.0294 (11)	0.0048 (12)	0.0095 (9)	0.0076 (12)
C7	0.0273 (12)	0.0422 (16)	0.0323 (14)	0.0010 (12)	0.0085 (11)	0.0025 (13)
N8	0.0216 (11)	0.087 (2)	0.0309 (13)	0.0034 (14)	0.0052 (10)	0.0097 (14)
N9	0.0341 (13)	0.0660 (19)	0.0284 (12)	0.0022 (13)	0.0062 (10)	0.0024 (13)
O11	0.0364 (10)	0.0700 (17)	0.0285 (10)	0.0032 (11)	0.0048 (9)	−0.0009 (11)
O12	0.102 (2)	0.0561 (15)	0.0474 (13)	0.0320 (15)	0.0369 (14)	0.0156 (12)
N11	0.0247 (12)	0.0541 (17)	0.0238 (12)	−0.0006 (11)	0.0045 (9)	−0.0020 (11)
C11	0.0423 (16)	0.055 (2)	0.0377 (16)	0.0255 (16)	0.0227 (13)	0.0132 (16)
C12	0.0337 (14)	0.0401 (16)	0.0348 (15)	0.0045 (13)	0.0055 (12)	0.0024 (13)
C13	0.0375 (15)	0.0504 (18)	0.0354 (15)	−0.0042 (14)	0.0114 (12)	0.0021 (14)
C14	0.0368 (15)	0.055 (2)	0.0376 (16)	0.0000 (14)	0.0104 (13)	0.0020 (14)
C15	0.0295 (14)	0.073 (2)	0.0467 (17)	−0.0026 (15)	0.0121 (13)	0.0046 (17)
N16	0.0369 (13)	0.0676 (19)	0.0345 (13)	−0.0149 (13)	0.0108 (11)	0.0080 (13)
C17	0.0360 (14)	0.0428 (16)	0.0286 (13)	−0.0071 (13)	0.0106 (11)	−0.0039 (12)
N18	0.0348 (13)	0.0676 (19)	0.0282 (13)	−0.0163 (13)	0.0069 (10)	−0.0008 (13)
N19	0.0464 (15)	0.070 (2)	0.0355 (14)	−0.0186 (15)	0.0041 (12)	0.0059 (14)
O21	0.0260 (9)	0.0392 (12)	0.0571 (13)	0.0015 (9)	−0.0009 (9)	0.0086 (10)
O22	0.0497 (12)	0.0426 (12)	0.0285 (10)	−0.0086 (10)	−0.0025 (9)	−0.0001 (10)
C23	0.0249 (12)	0.0323 (14)	0.0297 (13)	−0.0044 (11)	0.0031 (10)	0.0072 (12)
C24	0.0278 (13)	0.0340 (13)	0.0217 (12)	0.0018 (11)	0.0037 (10)	0.0015 (11)
O25	0.0354 (10)	0.0408 (12)	0.0280 (10)	0.0070 (9)	0.0034 (8)	−0.0069 (9)
C26	0.0321 (13)	0.0350 (15)	0.0217 (12)	0.0029 (12)	0.0068 (10)	−0.0034 (11)
O27	0.0406 (11)	0.0524 (13)	0.0243 (9)	−0.0025 (10)	0.0123 (8)	0.0012 (10)
C28	0.0283 (13)	0.0409 (16)	0.0250 (13)	0.0099 (12)	0.0058 (10)	−0.0055 (12)
O29	0.0295 (10)	0.0553 (14)	0.0489 (12)	0.0007 (11)	−0.0005 (9)	−0.0013 (11)
O30	0.0434 (12)	0.0530 (13)	0.0265 (10)	0.0083 (10)	0.0010 (9)	0.0030 (10)

Geometric parameters (Å, º)

O1—C1	1.248 (3)	C12—C13	1.544 (4)
O2—C1	1.242 (3)	C12—H12	0.9800
N1—C2	1.493 (4)	C13—C14	1.513 (4)
N1—H1A	0.89 (4)	C13—H13A	0.9700
N1—H1B	0.94 (3)	C13—H13B	0.9700
N1—H1C	0.91 (3)	C14—C15	1.517 (4)
C1—C2	1.534 (3)	C14—H14A	0.9700
C2—C3	1.525 (3)	C14—H14B	0.9700
C2—H2	0.9800	C15—N16	1.450 (4)
C3—C4	1.523 (4)	C15—H15A	0.9700
C3—H3A	0.9700	C15—H15B	0.9700
C3—H3B	0.9700	N16—C17	1.310 (4)
C4—C5	1.512 (4)	N16—H16	0.89 (3)
C4—H4A	0.9700	C17—N18	1.321 (4)
C4—H4B	0.9700	C17—N19	1.343 (4)
C5—N6	1.454 (4)	N18—H18A	0.89 (3)
C5—H5A	0.9700	N18—H18B	0.99 (4)
C5—H5B	0.9700	N19—H19A	0.90 (4)
N6—C7	1.319 (3)	N19—H19B	0.90 (5)
N6—H6	0.90 (3)	O21—C23	1.265 (4)
C7—N8	1.323 (4)	O22—C23	1.234 (4)
C7—N9	1.331 (4)	C23—C24	1.542 (3)
N8—H8A	0.82 (4)	C24—O25	1.417 (3)
N8—H8B	0.84 (3)	C24—C26	1.524 (3)
N9—H9A	0.86 (4)	C24—H24	0.9800
N9—H9B	0.88 (4)	O25—H25	0.83 (2)
O11—C11	1.260 (4)	C26—O27	1.424 (3)
O12—C11	1.221 (4)	C26—C28	1.531 (3)
N11—C12	1.494 (4)	C26—H26	0.9800
N11—H11A	0.84 (4)	O27—H27	0.86 (5)
N11—H11B	0.93 (3)	C28—O30	1.238 (4)
N11—H11C	0.92 (5)	C28—O29	1.271 (4)
C11—C12	1.532 (4)
C2—N1—H1A	110.5 (19)	N11—C12—C13	110.2 (3)
C2—N1—H1B	112 (2)	C11—C12—C13	105.9 (2)
H1A—N1—H1B	108 (3)	N11—C12—H12	110.5
C2—N1—H1C	110 (2)	C11—C12—H12	110.5
H1A—N1—H1C	107 (3)	C13—C12—H12	110.5
H1B—N1—H1C	110 (3)	C14—C13—C12	115.6 (2)
O2—C1—O1	125.7 (2)	C14—C13—H13A	108.4
O2—C1—C2	116.1 (2)	C12—C13—H13A	108.4
O1—C1—C2	118.1 (2)	C14—C13—H13B	108.4
N1—C2—C3	110.8 (2)	C12—C13—H13B	108.4
N1—C2—C1	110.2 (2)	H13A—C13—H13B	107.5
C3—C2—C1	112.8 (2)	C13—C14—C15	108.6 (2)
N1—C2—H2	107.6	C13—C14—H14A	110.0
C3—C2—H2	107.6	C15—C14—H14A	110.0
C1—C2—H2	107.6	C13—C14—H14B	110.0
C4—C3—C2	112.6 (2)	C15—C14—H14B	110.0
C4—C3—H3A	109.1	H14A—C14—H14B	108.3
C2—C3—H3A	109.1	N16—C15—C14	109.4 (2)
C4—C3—H3B	109.1	N16—C15—H15A	109.8
C2—C3—H3B	109.1	C14—C15—H15A	109.8
H3A—C3—H3B	107.8	N16—C15—H15B	109.8
C5—C4—C3	114.0 (3)	C14—C15—H15B	109.8
C5—C4—H4A	108.8	H15A—C15—H15B	108.2
C3—C4—H4A	108.8	C17—N16—C15	125.8 (3)
C5—C4—H4B	108.8	C17—N16—H16	111 (2)
C3—C4—H4B	108.8	C15—N16—H16	123 (2)
H4A—C4—H4B	107.6	N16—C17—N18	123.2 (3)
N6—C5—C4	111.7 (2)	N16—C17—N19	117.9 (3)
N6—C5—H5A	109.3	N18—C17—N19	118.9 (3)
C4—C5—H5A	109.3	C17—N18—H18A	124 (2)
N6—C5—H5B	109.3	C17—N18—H18B	114 (2)
C4—C5—H5B	109.3	H18A—N18—H18B	121 (3)
H5A—C5—H5B	107.9	C17—N19—H19A	117 (2)
C7—N6—C5	123.2 (2)	C17—N19—H19B	114 (3)
C7—N6—H6	121 (2)	H19A—N19—H19B	128 (4)
C5—N6—H6	115 (2)	O22—C23—O21	125.7 (2)
N6—C7—N8	121.7 (3)	O22—C23—C24	117.6 (2)
N6—C7—N9	119.8 (2)	O21—C23—C24	116.6 (2)
N8—C7—N9	118.6 (3)	O25—C24—C26	109.5 (2)
C7—N8—H8A	122 (2)	O25—C24—C23	112.3 (2)
C7—N8—H8B	118 (2)	C26—C24—C23	109.6 (2)
H8A—N8—H8B	120 (3)	O25—C24—H24	108.4
C7—N9—H9A	120 (2)	C26—C24—H24	108.4
C7—N9—H9B	115 (2)	C23—C24—H24	108.4
H9A—N9—H9B	125 (4)	C24—O25—H25	108 (3)
C12—N11—H11A	108 (3)	O27—C26—C24	110.6 (2)
C12—N11—H11B	116 (2)	O27—C26—C28	112.5 (2)
H11A—N11—H11B	112 (3)	C24—C26—C28	109.9 (2)
C12—N11—H11C	109 (2)	O27—C26—H26	107.9
H11A—N11—H11C	112 (4)	C24—C26—H26	107.9
H11B—N11—H11C	99 (3)	C28—C26—H26	107.9
O12—C11—O11	126.5 (3)	C26—O27—H27	114 (3)
O12—C11—C12	117.3 (3)	O30—C28—O29	125.9 (2)
O11—C11—C12	116.1 (3)	O30—C28—C26	116.9 (2)
N11—C12—C11	109.3 (2)	O29—C28—C26	117.1 (2)
O2—C1—C2—N1	−167.9 (2)	C12—C13—C14—C15	178.7 (3)
O1—C1—C2—N1	13.4 (3)	C13—C14—C15—N16	−177.7 (3)
O2—C1—C2—C3	−43.4 (3)	C14—C15—N16—C17	−127.5 (4)
O1—C1—C2—C3	137.9 (3)	C15—N16—C17—N18	−7.7 (5)
N1—C2—C3—C4	59.8 (3)	C15—N16—C17—N19	171.0 (3)
C1—C2—C3—C4	−64.4 (3)	O22—C23—C24—O25	173.4 (2)
C2—C3—C4—C5	159.6 (2)	O21—C23—C24—O25	−7.0 (3)
C3—C4—C5—N6	68.1 (4)	O22—C23—C24—C26	51.4 (3)
C4—C5—N6—C7	170.5 (3)	O21—C23—C24—C26	−129.0 (3)
C5—N6—C7—N8	4.8 (5)	O25—C24—C26—O27	−72.9 (3)
C5—N6—C7—N9	−175.8 (3)	C23—C24—C26—O27	50.7 (3)
O12—C11—C12—N11	151.9 (3)	O25—C24—C26—C28	51.9 (3)
O11—C11—C12—N11	−31.8 (3)	C23—C24—C26—C28	175.5 (2)
O12—C11—C12—C13	−89.4 (3)	O27—C26—C28—O30	−175.7 (2)
O11—C11—C12—C13	86.8 (3)	C24—C26—C28—O30	60.6 (3)
N11—C12—C13—C14	−59.8 (4)	O27—C26—C28—O29	3.2 (3)
C11—C12—C13—C14	−177.9 (3)	C24—C26—C28—O29	−120.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O21	0.89 (4)	2.01 (4)	2.892 (3)	171 (3)
N1—H1B···O11	0.94 (3)	1.82 (4)	2.759 (3)	177 (3)
N1—H1C···O22^i	0.91 (3)	1.86 (3)	2.770 (3)	176 (3)
N6—H6···O27^i	0.90 (3)	1.91 (3)	2.785 (3)	164 (3)
N8—H8A···O12^ii	0.82 (4)	2.16 (4)	2.961 (4)	167 (4)
N8—H8B···O21^iii	0.84 (3)	2.15 (3)	2.934 (3)	155 (3)
N9—H9A···O29^i	0.86 (4)	2.30 (4)	3.130 (4)	162 (3)
N9—H9B···O21^iii	0.88 (4)	2.33 (4)	3.127 (4)	151 (3)
N11—H11A···O1	0.84 (4)	2.22 (4)	3.046 (3)	166 (4)
N11—H11B···O30^iv	0.93 (3)	1.81 (3)	2.732 (3)	170 (3)
N11—H11C···O29	0.92 (5)	1.99 (5)	2.906 (4)	176 (3)
N16—H16···O2^v	0.89 (3)	1.92 (3)	2.781 (3)	162 (3)
N18—H18A···O1^vi	0.89 (3)	2.00 (4)	2.863 (3)	165 (3)
N18—H18B···O29^vii	0.99 (4)	1.86 (4)	2.840 (3)	168 (3)
N19—H19A···O2^v	0.90 (4)	2.03 (4)	2.841 (4)	149 (3)
N19—H19B···O29^vii	0.90 (5)	2.52 (5)	3.224 (4)	136 (4)
O25—H25···O1	0.83	2.23	2.840 (3)	131
O27—H27···O11	0.86 (5)	1.89 (5)	2.698 (4)	155 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+2; (v) −x+2, y−1/2, −z+2; (vi) x+1, y, z; (vii) −x+3, y+1/2, −z+2.

(III) DL-lysine DL-tartaric acid monohydrate complex

Crystal data

2(C6H15N4O2)^+·C4H4O6^2^−·H2O	F(000) = 992
Mr = 460.49	Dx = 1.400 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 732 reflections
a = 10.087 (3) Å	θ = 2.2–21.5°
b = 23.003 (8) Å	µ = 0.12 mm^−1
c = 9.414 (3) Å	T = 298 K
β = 90.820 (7)°	Needle, colourless
V = 2184.2 (13) Å^3	0.47 × 0.10 × 0.07 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	2876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ϕ and ω scan	h = −11→11
15605 measured reflections	k = −27→27
3842 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.1191P)^2 + 1.8406P] where P = (Fo^2 + 2Fc^2)/3
3842 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.75 e Å^−3
72 restraints	Δρmin = −0.30 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0134 (3)	0.27407 (11)	0.4861 (3)	0.0379 (7)
O2	0.0506 (3)	0.21428 (11)	0.3055 (3)	0.0354 (7)
N1	−0.0413 (3)	0.18627 (14)	0.6650 (3)	0.0292 (7)
C1	0.0305 (3)	0.22528 (15)	0.4347 (4)	0.0249 (8)
C2	0.0281 (4)	0.17145 (15)	0.5310 (4)	0.0266 (8)
H2	−0.0230	0.1410	0.4821	0.032*
C3	0.1655 (4)	0.14802 (16)	0.5622 (4)	0.0298 (8)
H3A	0.2043	0.1356	0.4736	0.036*
H3B	0.1577	0.1140	0.6224	0.036*
C4	0.2591 (4)	0.19074 (19)	0.6339 (5)	0.0434 (11)
H4A	0.2147	0.2084	0.7139	0.052*
H4B	0.2802	0.2214	0.5673	0.052*
C5	0.3889 (4)	0.1624 (2)	0.6870 (4)	0.0403 (10)
H5A	0.4359	0.1898	0.7477	0.048*
H5B	0.3674	0.1287	0.7442	0.048*
C6	0.4792 (4)	0.14372 (19)	0.5696 (4)	0.0384 (10)
H6A	0.4374	0.1127	0.5153	0.046*
H6B	0.4939	0.1762	0.5060	0.046*
N7	0.6089 (3)	0.12301 (17)	0.6284 (4)	0.0361 (8)
O11	0.7280 (3)	0.27196 (11)	0.0007 (3)	0.0388 (7)
O12	0.6893 (3)	0.21413 (12)	−0.1837 (3)	0.0394 (7)
N11	0.7798 (4)	0.18248 (15)	0.1768 (3)	0.0275 (7)
C11	0.7100 (3)	0.22335 (16)	−0.0534 (4)	0.0271 (8)
C12	0.7115 (4)	0.16932 (17)	0.0403 (4)	0.0334 (9)
H12	0.7677	0.1410	−0.0081	0.040*
C13A	0.5804 (4)	0.1386 (2)	0.0653 (5)	0.0310 (12)	0.764 (7)
H13A	0.5950	0.1048	0.1253	0.037*	0.764 (7)
H13B	0.5430	0.1255	−0.0246	0.037*	0.764 (7)
C14A	0.4837 (4)	0.1803 (2)	0.1371 (6)	0.0396 (13)	0.764 (7)
H14A	0.4636	0.2120	0.0724	0.047*	0.764 (7)
H14B	0.5266	0.1967	0.2208	0.047*	0.764 (7)
C15A	0.3529 (5)	0.1512 (3)	0.1813 (5)	0.0366 (14)	0.764 (7)
H15A	0.3740	0.1170	0.2374	0.044*	0.764 (7)
H15B	0.3053	0.1780	0.2418	0.044*	0.764 (7)
C13B	0.5638 (7)	0.1712 (7)	0.076 (2)	0.041 (3)	0.236 (7)
H13C	0.5156	0.1747	−0.0139	0.049*	0.236 (7)
H13D	0.5489	0.2069	0.1276	0.049*	0.236 (7)
C14B	0.4973 (13)	0.1222 (7)	0.1595 (17)	0.036 (2)	0.236 (7)
H14C	0.5440	0.1189	0.2500	0.044*	0.236 (7)
H14D	0.5126	0.0862	0.1085	0.044*	0.236 (7)
C15B	0.3483 (12)	0.1252 (10)	0.1912 (10)	0.033 (4)	0.236 (7)
H15C	0.3224	0.0897	0.2389	0.040*	0.236 (7)
H15D	0.3328	0.1573	0.2556	0.040*	0.236 (7)
C16	0.2610 (4)	0.13317 (19)	0.0588 (4)	0.0384 (10)
H16A	0.2577	0.1642	−0.0110	0.046*
H16B	0.2973	0.0990	0.0132	0.046*
N17	0.1247 (3)	0.12019 (16)	0.1053 (4)	0.0280 (7)
O21	0.7543 (3)	0.09446 (11)	0.3905 (3)	0.0373 (7)
O22	0.7501 (3)	0.00534 (12)	0.4799 (3)	0.0377 (7)
C23	0.7810 (3)	0.04184 (16)	0.3854 (4)	0.0259 (8)
C24	0.8552 (3)	0.01767 (14)	0.2566 (4)	0.0241 (8)
H24	0.8050	−0.0153	0.2178	0.029*
O25	0.8629 (3)	0.06098 (11)	0.1511 (3)	0.0297 (6)
C26	0.9936 (3)	−0.00365 (14)	0.3015 (3)	0.0222 (7)
H26	0.9848	−0.0308	0.3811	0.027*
O27	1.0669 (3)	0.04550 (10)	0.3483 (2)	0.0285 (6)
H27	1.1293	0.0348	0.3987	0.034*
C28	1.0578 (4)	−0.03539 (15)	0.1778 (4)	0.0250 (8)
O29	1.1434 (3)	−0.00923 (11)	0.1073 (3)	0.0353 (7)
O30	1.0169 (3)	−0.08603 (11)	0.1534 (3)	0.0377 (7)
O1W	0.5810 (10)	0.0235 (4)	0.8233 (12)	0.044 (3)	0.33
O2W	0.5197 (7)	0.0006 (4)	0.6244 (9)	0.043 (2)	0.34
O3W	0.5695 (10)	0.0083 (5)	0.9114 (15)	0.064 (3)	0.33
H1A	−0.042 (5)	0.154 (2)	0.735 (5)	0.057 (13)*
H1B	−0.137 (5)	0.194 (2)	0.635 (5)	0.062 (15)*
H1C	0.010 (5)	0.221 (2)	0.715 (5)	0.054 (13)*
H7A	0.647 (5)	0.151 (2)	0.693 (5)	0.064 (15)*
H7B	0.670 (5)	0.111 (2)	0.549 (6)	0.069 (16)*
H7C	0.593 (4)	0.0920 (18)	0.684 (4)	0.028 (11)*
H11A	0.862 (5)	0.1893 (16)	0.153 (4)	0.031 (11)*
H11B	0.788 (5)	0.151 (2)	0.222 (6)	0.063 (16)*
H11C	0.749 (5)	0.213 (2)	0.225 (5)	0.042 (12)*
H17A	0.130 (5)	0.087 (2)	0.146 (5)	0.057 (15)*
H17B	0.069 (5)	0.106 (2)	0.026 (6)	0.065 (15)*
H17C	0.102 (4)	0.144 (2)	0.158 (5)	0.035 (13)*
H25	0.877 (5)	0.043 (2)	0.071 (6)	0.070 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0555 (18)	0.0255 (15)	0.0327 (15)	0.0007 (12)	−0.0053 (13)	−0.0008 (11)
O2	0.0471 (17)	0.0356 (15)	0.0237 (14)	0.0048 (12)	0.0051 (11)	0.0014 (11)
N1	0.0334 (19)	0.0283 (17)	0.0260 (17)	−0.0004 (14)	0.0043 (13)	0.0036 (14)
C1	0.0247 (18)	0.0265 (19)	0.0233 (18)	−0.0009 (15)	−0.0030 (14)	−0.0004 (15)
C2	0.0282 (19)	0.0277 (19)	0.0240 (18)	0.0021 (15)	0.0009 (14)	0.0001 (15)
C3	0.030 (2)	0.029 (2)	0.030 (2)	0.0037 (16)	0.0012 (16)	0.0000 (15)
C4	0.036 (2)	0.040 (2)	0.055 (3)	0.0038 (19)	−0.006 (2)	−0.009 (2)
C5	0.029 (2)	0.054 (3)	0.037 (2)	0.0042 (19)	−0.0030 (17)	−0.0097 (19)
C6	0.031 (2)	0.051 (3)	0.032 (2)	0.0005 (18)	−0.0031 (17)	−0.0059 (18)
N7	0.0295 (19)	0.040 (2)	0.038 (2)	0.0032 (15)	0.0045 (16)	−0.0058 (18)
O11	0.0478 (17)	0.0312 (15)	0.0375 (16)	0.0026 (12)	0.0004 (13)	0.0006 (12)
O12	0.0528 (18)	0.0418 (16)	0.0236 (15)	−0.0088 (13)	−0.0070 (12)	0.0064 (12)
N11	0.0286 (19)	0.0261 (18)	0.0277 (17)	−0.0011 (15)	−0.0020 (14)	0.0024 (15)
C11	0.0212 (18)	0.031 (2)	0.029 (2)	−0.0014 (15)	0.0005 (14)	0.0030 (16)
C12	0.039 (2)	0.037 (2)	0.0243 (19)	−0.0091 (17)	−0.0016 (16)	0.0019 (16)
C13A	0.036 (3)	0.021 (3)	0.036 (3)	−0.007 (2)	−0.003 (2)	0.001 (2)
C14A	0.035 (3)	0.036 (3)	0.048 (3)	−0.005 (2)	−0.004 (2)	−0.009 (2)
C15A	0.031 (3)	0.041 (4)	0.039 (3)	−0.006 (3)	0.005 (2)	−0.006 (3)
C13B	0.041 (6)	0.041 (6)	0.041 (5)	−0.016 (6)	0.001 (5)	0.004 (6)
C14B	0.032 (4)	0.037 (5)	0.040 (5)	−0.006 (4)	0.003 (4)	−0.001 (4)
C15B	0.025 (6)	0.041 (8)	0.034 (6)	−0.008 (6)	0.006 (5)	−0.003 (6)
C16	0.033 (2)	0.050 (2)	0.032 (2)	0.0003 (18)	0.0088 (17)	−0.0022 (18)
N17	0.0280 (18)	0.0235 (18)	0.0326 (19)	−0.0012 (14)	0.0012 (15)	0.0008 (16)
O21	0.0492 (17)	0.0300 (15)	0.0331 (15)	0.0115 (12)	0.0129 (12)	0.0011 (11)
O22	0.0365 (16)	0.0429 (16)	0.0339 (15)	0.0074 (12)	0.0103 (12)	0.0153 (12)
C23	0.0220 (18)	0.029 (2)	0.0264 (19)	0.0027 (15)	0.0016 (14)	0.0030 (15)
C24	0.0301 (19)	0.0196 (17)	0.0228 (18)	0.0002 (14)	−0.0008 (14)	−0.0001 (14)
O25	0.0445 (16)	0.0259 (14)	0.0189 (13)	0.0085 (11)	0.0026 (11)	0.0030 (10)
C26	0.0293 (19)	0.0176 (17)	0.0199 (16)	−0.0016 (14)	0.0024 (14)	0.0015 (13)
O27	0.0340 (15)	0.0258 (13)	0.0256 (13)	−0.0021 (10)	−0.0052 (11)	−0.0020 (10)
C28	0.033 (2)	0.0216 (18)	0.0208 (17)	0.0047 (15)	−0.0003 (14)	0.0037 (14)
O29	0.0407 (16)	0.0359 (15)	0.0298 (15)	−0.0046 (12)	0.0127 (12)	−0.0033 (11)
O30	0.065 (2)	0.0197 (14)	0.0281 (14)	−0.0012 (12)	0.0071 (13)	−0.0030 (11)
O1W	0.031 (5)	0.045 (6)	0.058 (6)	0.008 (4)	0.008 (5)	0.037 (5)
O2W	0.022 (4)	0.055 (5)	0.052 (5)	−0.007 (4)	0.016 (4)	0.014 (4)
O3W	0.026 (5)	0.063 (8)	0.102 (10)	−0.009 (5)	0.017 (6)	−0.045 (7)

Geometric parameters (Å, º)

O1—C1	1.235 (4)	C13A—H13B	0.9700
O2—C1	1.261 (4)	C14A—C15A	1.542 (5)
N1—C2	1.491 (4)	C14A—H14A	0.9700
N1—H1A	0.99 (5)	C14A—H14B	0.9700
N1—H1B	1.02 (5)	C15A—C16	1.527 (5)
N1—H1C	1.06 (5)	C15A—H15A	0.9700
C1—C2	1.535 (5)	C15A—H15B	0.9700
C2—C3	1.512 (5)	C13B—C14B	1.536 (6)
C2—H2	0.9800	C13B—H13C	0.9700
C3—C4	1.515 (5)	C13B—H13D	0.9700
C3—H3A	0.9700	C14B—C15B	1.538 (6)
C3—H3B	0.9700	C14B—H14C	0.9700
C4—C5	1.540 (6)	C14B—H14D	0.9700
C4—H4A	0.9700	C15B—C16	1.527 (6)
C4—H4B	0.9700	C15B—H15C	0.9700
C5—C6	1.504 (5)	C15B—H15D	0.9700
C5—H5A	0.9700	C16—N17	1.479 (5)
C5—H5B	0.9700	C16—H16A	0.9700
C6—N7	1.492 (5)	C16—H16B	0.9700
C6—H6A	0.9700	N17—H17A	0.85 (6)
C6—H6B	0.9700	N17—H17B	0.98 (6)
N7—H7A	0.96 (6)	N17—H17C	0.78 (5)
N7—H7B	1.02 (6)	O21—C23	1.241 (4)
N7—H7C	0.90 (4)	O22—C23	1.265 (4)
O11—C11	1.241 (4)	C23—C24	1.539 (5)
O12—C11	1.259 (4)	C24—O25	1.409 (4)
N11—C12	1.481 (5)	C24—C26	1.534 (5)
N11—H11A	0.87 (5)	C24—H24	0.9800
N11—H11B	0.84 (5)	O25—H25	0.88 (6)
N11—H11C	0.90 (5)	C26—O27	1.418 (4)
C11—C12	1.524 (5)	C26—C28	1.526 (5)
C12—C13A	1.520 (5)	C26—H26	0.9800
C12—C13B	1.531 (6)	O27—H27	0.8200
C12—H12	0.9800	C28—O29	1.252 (4)
C13A—C14A	1.532 (5)	C28—O30	1.256 (4)
C13A—H13A	0.9700
C2—N1—H1A	114 (3)	C14A—C13A—H13B	109.7
C2—N1—H1B	105 (3)	H13A—C13A—H13B	108.2
H1A—N1—H1B	108 (4)	C13A—C14A—C15A	113.6 (4)
C2—N1—H1C	109 (3)	C13A—C14A—H14A	108.8
H1A—N1—H1C	106 (4)	C15A—C14A—H14A	108.8
H1B—N1—H1C	116 (4)	C13A—C14A—H14B	108.8
O1—C1—O2	125.8 (3)	C15A—C14A—H14B	108.8
O1—C1—C2	119.9 (3)	H14A—C14A—H14B	107.7
O2—C1—C2	114.3 (3)	C16—C15A—C14A	115.3 (4)
N1—C2—C3	110.9 (3)	C16—C15A—H15A	108.4
N1—C2—C1	109.1 (3)	C14A—C15A—H15A	108.4
C3—C2—C1	112.3 (3)	C16—C15A—H15B	108.4
N1—C2—H2	108.1	C14A—C15A—H15B	108.4
C3—C2—H2	108.1	H15A—C15A—H15B	107.5
C1—C2—H2	108.1	C12—C13B—C14B	121.7 (10)
C2—C3—C4	114.8 (3)	C12—C13B—H13C	106.9
C2—C3—H3A	108.6	C14B—C13B—H13C	106.9
C4—C3—H3A	108.6	C12—C13B—H13D	106.9
C2—C3—H3B	108.6	C14B—C13B—H13D	106.9
C4—C3—H3B	108.6	H13C—C13B—H13D	106.7
H3A—C3—H3B	107.5	C13B—C14B—C15B	120.1 (12)
C3—C4—C5	113.0 (3)	C13B—C14B—H14C	107.3
C3—C4—H4A	109.0	C15B—C14B—H14C	107.3
C5—C4—H4A	109.0	C13B—C14B—H14D	107.3
C3—C4—H4B	109.0	C15B—C14B—H14D	107.3
C5—C4—H4B	109.0	H14C—C14B—H14D	106.9
H4A—C4—H4B	107.8	C16—C15B—C14B	113.7 (10)
C6—C5—C4	113.8 (3)	C16—C15B—H15C	108.8
C6—C5—H5A	108.8	C14B—C15B—H15C	108.8
C4—C5—H5A	108.8	C16—C15B—H15D	108.8
C6—C5—H5B	108.8	C14B—C15B—H15D	108.8
C4—C5—H5B	108.8	H15C—C15B—H15D	107.7
H5A—C5—H5B	107.7	N17—C16—C15A	112.8 (3)
N7—C6—C5	110.8 (3)	N17—C16—C15B	105.2 (6)
N7—C6—H6A	109.5	N17—C16—H16A	109.0
C5—C6—H6A	109.5	C15A—C16—H16A	109.0
N7—C6—H6B	109.5	C15B—C16—H16A	130.9
C5—C6—H6B	109.5	N17—C16—H16B	109.0
H6A—C6—H6B	108.1	C15A—C16—H16B	109.0
C6—N7—H7A	111 (3)	C15B—C16—H16B	92.7
C6—N7—H7B	111 (3)	H16A—C16—H16B	107.8
H7A—N7—H7B	114 (4)	C16—N17—H17A	105 (3)
C6—N7—H7C	108 (3)	C16—N17—H17B	111 (3)
H7A—N7—H7C	104 (4)	H17A—N17—H17B	95 (4)
H7B—N7—H7C	108 (4)	C16—N17—H17C	109 (3)
C12—N11—H11A	104 (3)	H17A—N17—H17C	111 (5)
C12—N11—H11B	108 (4)	H17B—N17—H17C	123 (4)
H11A—N11—H11B	102 (4)	O21—C23—O22	124.4 (3)
C12—N11—H11C	116 (3)	O21—C23—C24	119.4 (3)
H11A—N11—H11C	109 (4)	O22—C23—C24	116.2 (3)
H11B—N11—H11C	116 (5)	O25—C24—C26	111.2 (3)
O11—C11—O12	125.0 (3)	O25—C24—C23	109.4 (3)
O11—C11—C12	119.8 (3)	C26—C24—C23	110.5 (3)
O12—C11—C12	115.3 (3)	O25—C24—H24	108.6
N11—C12—C13A	110.8 (3)	C26—C24—H24	108.6
N11—C12—C11	109.7 (3)	C23—C24—H24	108.6
C13A—C12—C11	117.9 (3)	C24—O25—H25	106 (4)
N11—C12—C13B	104.4 (8)	O27—C26—C28	113.2 (3)
C11—C12—C13B	95.8 (6)	O27—C26—C24	107.4 (3)
N11—C12—H12	105.9	C28—C26—C24	109.7 (3)
C13A—C12—H12	105.9	O27—C26—H26	108.8
C11—C12—H12	105.9	C28—C26—H26	108.8
C13B—C12—H12	133.7	C24—C26—H26	108.8
C12—C13A—C14A	109.7 (4)	C26—O27—H27	109.5
C12—C13A—H13A	109.7	O29—C28—O30	125.2 (3)
C14A—C13A—H13A	109.7	O29—C28—C26	118.6 (3)
C12—C13A—H13B	109.7	O30—C28—C26	116.2 (3)
O1—C1—C2—N1	19.6 (5)	N11—C12—C13B—C14B	−74.1 (17)
O2—C1—C2—N1	−160.3 (3)	C11—C12—C13B—C14B	173.8 (16)
O1—C1—C2—C3	−103.8 (4)	C12—C13B—C14B—C15B	−179.2 (14)
O2—C1—C2—C3	76.3 (4)	C13B—C14B—C15B—C16	55 (2)
N1—C2—C3—C4	−63.5 (4)	C14A—C15A—C16—N17	−164.9 (4)
C1—C2—C3—C4	58.9 (4)	C14B—C15B—C16—N17	166.1 (13)
C2—C3—C4—C5	170.0 (3)	O21—C23—C24—O25	−9.1 (4)
C3—C4—C5—C6	69.8 (5)	O22—C23—C24—O25	170.3 (3)
C4—C5—C6—N7	173.5 (4)	O21—C23—C24—C26	113.6 (4)
O11—C11—C12—N11	−19.3 (5)	O22—C23—C24—C26	−67.0 (4)
O12—C11—C12—N11	160.9 (3)	O25—C24—C26—O27	56.8 (3)
O11—C11—C12—C13A	108.7 (4)	C23—C24—C26—O27	−64.8 (3)
O12—C11—C12—C13A	−71.1 (5)	O25—C24—C26—C28	−66.6 (3)
O11—C11—C12—C13B	88.2 (9)	C23—C24—C26—C28	171.8 (3)
O12—C11—C12—C13B	−91.6 (9)	O27—C26—C28—O29	−18.0 (4)
N11—C12—C13A—C14A	67.3 (5)	C24—C26—C28—O29	102.0 (4)
C11—C12—C13A—C14A	−60.1 (5)	O27—C26—C28—O30	163.6 (3)
C12—C13A—C14A—C15A	−173.9 (4)	C24—C26—C28—O30	−76.5 (4)
C13A—C14A—C15A—C16	−69.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O30^i	0.99 (5)	1.90 (5)	2.879 (4)	168 (4)
N1—H1B···O11^ii	1.02 (5)	2.00 (5)	2.938 (5)	151 (4)
N1—H1C···O2^iii	1.06 (5)	1.75 (5)	2.794 (4)	165 (4)
N7—H7A···O12^iv	0.96 (6)	1.90 (6)	2.852 (5)	169 (5)
N7—H7B···O21	1.02 (6)	1.77 (6)	2.774 (4)	169 (5)
N7—H7C···O1W	0.90 (4)	2.06 (4)	2.950 (9)	172 (4)
N7—H7C···O2W	0.90 (4)	2.30 (4)	2.956 (9)	130 (3)
N11—H11A···O1^v	0.87 (5)	2.36 (5)	3.146 (5)	149 (3)
N11—H11A···O2^vi	0.87 (5)	2.44 (4)	3.061 (4)	129 (3)
N11—H11B···O21	0.84 (5)	2.09 (6)	2.868 (4)	155 (5)
N11—H11B···O25	0.84 (5)	2.31 (5)	2.929 (4)	131 (4)
N11—H11C···O12^iii	0.90 (5)	1.98 (5)	2.872 (5)	174 (4)
N17—H17A···O27^vii	0.85 (6)	2.24 (5)	2.926 (4)	138 (4)
N17—H17A···O29^vii	0.85 (6)	2.25 (6)	2.983 (5)	144 (4)
N17—H17B···O30^viii	0.98 (6)	1.94 (6)	2.915 (5)	169 (4)
N17—H17C···O2	0.78 (5)	2.20 (5)	2.972 (5)	176 (4)
O25—H25···O29^ix	0.88 (6)	1.85 (6)	2.708 (4)	164 (5)
O27—H27···O22^x	0.82	1.90	2.702 (4)	167
O3W—O29···2.904 (1)^xi	3_756	O3W	O1W	3 (1)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −y+1/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) x, y, z+1; (v) x+1, −y+1/2, z−1/2; (vi) x+1, y, z; (vii) x−1, y, z; (viii) −x+1, −y, −z; (ix) −x+2, −y, −z; (x) −x+2, −y, −z+1; (xi) −x+1, −y, −z+2.

(IV) L-lysine D-hydrogen tartrate

Crystal data

C6H15N2O2^+·C4H5O6^−	F(000) = 316
Mr = 296.28	Dx = 1.494 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1435 reflections
a = 5.1849 (11) Å	θ = 2.4–21.5°
b = 16.667 (4) Å	µ = 0.13 mm^−1
c = 7.6701 (17) Å	T = 2983 K
β = 96.366 (4)°	Plate, colourless
V = 658.7 (2) Å^3	0.4 × 0.35 × 0.2 mm
Z = 2

Data collection

Bruker SMART CCD area detector diffractometer	1231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 26.0°, θmin = 2.4°
ϕ and ω scan	h = −6→6
4251 measured reflections	k = −20→17
1342 independent reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.0738P] where P = (Fo^2 + 2Fc^2)/3
1342 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.15 e Å^−3
79 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N7	0.3338 (7)	0.3679 (2)	0.8340 (4)	0.0379 (7)
C3	−0.1426 (6)	0.5083 (2)	0.3292 (4)	0.0344 (8)
H3A	−0.2058	0.5413	0.4195	0.041*
H3B	−0.2673	0.4655	0.3014	0.041*
C4	0.1164 (6)	0.4714 (2)	0.4015 (4)	0.0335 (7)
H4A	0.1681	0.4320	0.3191	0.040*
H4B	0.2481	0.5129	0.4147	0.040*
C5	0.0981 (6)	0.4319 (2)	0.5762 (4)	0.0332 (7)
H5A	−0.0344	0.3905	0.5622	0.040*
H5B	0.0448	0.4715	0.6577	0.040*
C6	0.3511 (6)	0.3947 (2)	0.6526 (4)	0.0378 (8)
H6A	0.3917	0.3494	0.5813	0.045*
H6B	0.4897	0.4338	0.6514	0.045*
N1	−0.3834 (6)	0.5972 (2)	0.1137 (4)	0.0347 (7)
C1A	−0.0476 (7)	0.5043 (3)	0.0209 (6)	0.0367 (14)	0.815 (11)
O1A	−0.2208 (7)	0.4677 (4)	−0.0683 (6)	0.0633 (18)	0.815 (11)
O2A	0.1872 (8)	0.4939 (4)	0.0151 (7)	0.0462 (16)	0.815 (11)
C2	−0.1273 (6)	0.5593 (2)	0.1655 (4)	0.0290 (7)
H2	0.0042	0.6012	0.1909	0.035*
C1B	−0.050 (2)	0.525 (2)	−0.0078 (17)	0.045 (4)	0.185 (11)
O1B	−0.219 (3)	0.5240 (17)	−0.1343 (15)	0.057 (5)	0.185 (11)
O2B	0.185 (2)	0.5208 (17)	−0.019 (2)	0.041 (5)	0.185 (11)
O11	0.7396 (4)	0.25423 (15)	−0.0671 (3)	0.0367 (6)
O12	1.1371 (4)	0.23138 (18)	0.0588 (3)	0.0436 (7)
C13	0.9078 (6)	0.24863 (18)	0.0650 (3)	0.0245 (6)
C14	0.8172 (6)	0.26391 (19)	0.2467 (4)	0.0263 (7)
H14	0.9471	0.2984	0.3120	0.032*
O15	0.5765 (5)	0.30320 (16)	0.2419 (3)	0.0358 (6)
C16	0.8172 (7)	0.1839 (2)	0.3447 (4)	0.0310 (7)
H16	0.9924	0.1610	0.3560	0.037*
O17	0.6431 (5)	0.13050 (16)	0.2485 (3)	0.0478 (7)
H17	0.7252	0.0943	0.2078	0.057*
C18	0.7312 (6)	0.1959 (2)	0.5264 (4)	0.0294 (7)
O19	0.5315 (5)	0.16599 (17)	0.5662 (3)	0.0476 (7)
O20	0.8893 (4)	0.23808 (15)	0.6323 (3)	0.0367 (6)
H1A	−0.371 (7)	0.629 (3)	0.023 (5)	0.048 (11)*
H1B	−0.446 (8)	0.623 (3)	0.206 (6)	0.048 (11)*
H1C	−0.497 (9)	0.561 (3)	0.084 (5)	0.052 (13)*
H7A	0.276 (7)	0.413 (3)	0.909 (5)	0.049 (11)*
H7B	0.464 (8)	0.345 (3)	0.886 (5)	0.045 (11)*
H7C	0.207 (10)	0.331 (3)	0.846 (6)	0.067 (14)*
H15	0.453 (9)	0.277 (3)	0.182 (6)	0.064 (15)*
H20	0.836 (9)	0.239 (3)	0.749 (6)	0.077 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N7	0.0319 (16)	0.0392 (19)	0.0424 (16)	0.0078 (16)	0.0029 (13)	0.0062 (15)
C3	0.0330 (17)	0.0359 (19)	0.0359 (18)	0.0052 (15)	0.0113 (14)	0.0048 (14)
C4	0.0312 (16)	0.038 (2)	0.0321 (15)	0.0014 (15)	0.0071 (12)	0.0001 (15)
C5	0.0272 (16)	0.035 (2)	0.0375 (17)	0.0035 (14)	0.0060 (13)	−0.0028 (14)
C6	0.0317 (18)	0.048 (2)	0.0344 (19)	0.0053 (16)	0.0066 (14)	−0.0003 (15)
N1	0.0424 (18)	0.0363 (18)	0.0265 (14)	0.0061 (15)	0.0086 (13)	0.0006 (14)
C1A	0.033 (2)	0.048 (3)	0.032 (2)	−0.006 (2)	0.0141 (18)	−0.006 (2)
O1A	0.038 (2)	0.084 (4)	0.070 (3)	−0.018 (2)	0.0154 (18)	−0.045 (3)
O2A	0.034 (2)	0.064 (4)	0.043 (2)	−0.0026 (18)	0.0142 (16)	−0.017 (2)
C2	0.0297 (17)	0.0290 (18)	0.0290 (16)	0.0002 (14)	0.0063 (13)	−0.0025 (13)
C1B	0.032 (7)	0.062 (8)	0.041 (7)	−0.003 (6)	0.008 (6)	−0.021 (7)
O1B	0.037 (7)	0.085 (11)	0.049 (8)	0.006 (8)	0.002 (6)	−0.034 (7)
O2B	0.025 (7)	0.066 (11)	0.035 (8)	−0.013 (7)	0.014 (6)	−0.003 (8)
O11	0.0372 (13)	0.0517 (16)	0.0208 (10)	0.0112 (11)	0.0018 (9)	−0.0040 (10)
O12	0.0262 (12)	0.0686 (19)	0.0368 (13)	0.0042 (13)	0.0064 (9)	−0.0096 (12)
C13	0.0265 (15)	0.0255 (17)	0.0221 (14)	−0.0032 (13)	0.0057 (12)	−0.0001 (12)
C14	0.0255 (15)	0.0301 (18)	0.0228 (14)	0.0005 (13)	0.0005 (12)	−0.0035 (12)
O15	0.0407 (14)	0.0349 (13)	0.0329 (12)	0.0100 (11)	0.0096 (10)	−0.0047 (10)
C16	0.0390 (18)	0.0307 (19)	0.0232 (14)	0.0034 (14)	0.0023 (13)	−0.0010 (13)
O17	0.0730 (19)	0.0342 (14)	0.0352 (14)	−0.0064 (13)	0.0012 (12)	−0.0073 (11)
C18	0.0349 (17)	0.0302 (17)	0.0234 (14)	0.0011 (14)	0.0041 (13)	0.0051 (13)
O19	0.0506 (15)	0.0603 (17)	0.0333 (13)	−0.0233 (13)	0.0117 (11)	0.0021 (12)
O20	0.0426 (13)	0.0478 (16)	0.0199 (10)	−0.0120 (12)	0.0043 (9)	−0.0027 (10)

Geometric parameters (Å, º)

N7—C6	1.474 (4)	C1A—O2A	1.235 (4)
N7—H7A	1.01 (4)	C1A—C2	1.531 (5)
N7—H7B	0.84 (5)	C2—C1B	1.539 (9)
N7—H7C	0.91 (6)	C2—H2	0.9800
C3—C4	1.524 (5)	C1B—O1B	1.233 (5)
C3—C2	1.526 (4)	C1B—O2B	1.235 (5)
C3—H3A	0.9700	O11—C13	1.264 (4)
C3—H3B	0.9700	O12—C13	1.229 (4)
C4—C5	1.506 (4)	C13—C14	1.541 (4)
C4—H4A	0.9700	C14—O15	1.406 (4)
C4—H4B	0.9700	C14—C16	1.531 (4)
C5—C6	1.509 (5)	C14—H14	0.9800
C5—H5A	0.9700	O15—H15	0.87 (5)
C5—H5B	0.9700	C16—O17	1.416 (4)
C6—H6A	0.9700	C16—C18	1.523 (4)
C6—H6B	0.9700	C16—H16	0.9800
N1—C2	1.484 (4)	O17—H17	0.8200
N1—H1A	0.89 (4)	C18—O19	1.218 (4)
N1—H1B	0.91 (4)	C18—O20	1.296 (4)
N1—H1C	0.86 (5)	O20—H20	0.96 (5)
C1A—O1A	1.229 (4)
C6—N7—H7A	111 (2)	O1A—C1A—O2A	124.9 (4)
C6—N7—H7B	117 (3)	O1A—C1A—C2	117.5 (3)
H7A—N7—H7B	110 (4)	O2A—C1A—C2	117.1 (3)
C6—N7—H7C	115 (3)	N1—C2—C3	109.3 (2)
H7A—N7—H7C	100 (4)	N1—C2—C1A	111.5 (3)
H7B—N7—H7C	101 (4)	C3—C2—C1A	107.8 (3)
C4—C3—C2	113.6 (2)	N1—C2—C1B	103.7 (7)
C4—C3—H3A	108.8	C3—C2—C1B	123.1 (14)
C2—C3—H3A	108.8	N1—C2—H2	109.4
C4—C3—H3B	108.8	C3—C2—H2	109.4
C2—C3—H3B	108.8	C1A—C2—H2	109.4
H3A—C3—H3B	107.7	C1B—C2—H2	101.1
C5—C4—C3	111.1 (2)	O1B—C1B—O2B	124.3 (10)
C5—C4—H4A	109.4	O1B—C1B—C2	117.1 (8)
C3—C4—H4A	109.4	O2B—C1B—C2	115.9 (8)
C5—C4—H4B	109.4	O12—C13—O11	124.8 (3)
C3—C4—H4B	109.4	O12—C13—C14	117.8 (3)
H4A—C4—H4B	108.0	O11—C13—C14	117.4 (2)
C4—C5—C6	112.8 (3)	O15—C14—C16	111.7 (2)
C4—C5—H5A	109.0	O15—C14—C13	114.3 (2)
C6—C5—H5A	109.0	C16—C14—C13	108.5 (2)
C4—C5—H5B	109.0	O15—C14—H14	107.3
C6—C5—H5B	109.0	C16—C14—H14	107.3
H5A—C5—H5B	107.8	C13—C14—H14	107.3
N7—C6—C5	110.5 (3)	C14—O15—H15	112 (3)
N7—C6—H6A	109.6	O17—C16—C18	109.0 (3)
C5—C6—H6A	109.6	O17—C16—C14	109.1 (2)
N7—C6—H6B	109.6	C18—C16—C14	110.5 (3)
C5—C6—H6B	109.6	O17—C16—H16	109.4
H6A—C6—H6B	108.1	C18—C16—H16	109.4
C2—N1—H1A	109 (2)	C14—C16—H16	109.4
C2—N1—H1B	112 (3)	C16—O17—H17	109.5
H1A—N1—H1B	113 (4)	O19—C18—O20	124.2 (3)
C2—N1—H1C	110 (3)	O19—C18—C16	121.3 (3)
H1A—N1—H1C	109 (4)	O20—C18—C16	114.6 (3)
H1B—N1—H1C	104 (4)	C18—O20—H20	111 (3)
C2—C3—C4—C5	171.8 (3)	C3—C2—C1B—O2B	−85 (3)
C3—C4—C5—C6	−179.9 (3)	O12—C13—C14—O15	164.1 (3)
C4—C5—C6—N7	171.4 (3)	O11—C13—C14—O15	−16.4 (4)
C4—C3—C2—N1	−175.8 (3)	O12—C13—C14—C16	−70.5 (4)
C4—C3—C2—C1A	62.9 (4)	O11—C13—C14—C16	109.0 (3)
C4—C3—C2—C1B	62.3 (8)	O15—C14—C16—O17	66.2 (3)
O1A—C1A—C2—N1	−34.1 (6)	C13—C14—C16—O17	−60.7 (3)
O2A—C1A—C2—N1	153.2 (5)	O15—C14—C16—C18	−53.6 (3)
O1A—C1A—C2—C3	85.8 (6)	C13—C14—C16—C18	179.5 (2)
O2A—C1A—C2—C3	−86.8 (5)	O17—C16—C18—O19	−4.4 (4)
N1—C2—C1B—O1B	−11 (3)	C14—C16—C18—O19	115.4 (4)
C3—C2—C1B—O1B	113 (2)	O17—C16—C18—O20	174.1 (3)
N1—C2—C1B—O2B	151 (2)	C14—C16—C18—O20	−66.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O12^i	0.89 (4)	2.22 (4)	2.959 (4)	141 (3)
N1—H1A···O17^ii	0.89 (4)	2.38 (4)	3.001 (4)	127 (3)
N1—H1B···O19^iii	0.91 (4)	1.99 (4)	2.890 (4)	169 (4)
N1—H1C···O2A^iv	0.86 (5)	2.00 (5)	2.849 (6)	169 (4)
N7—H7A···O2A^v	1.01 (4)	1.67 (5)	2.675 (5)	174 (4)
N7—H7B···O11^v	0.84 (5)	2.08 (5)	2.870 (4)	156 (4)
N7—H7C···O12^vi	0.91 (6)	2.38 (5)	3.095 (4)	135 (4)
O15—H15···O12^iv	0.87 (5)	1.95 (5)	2.808 (4)	170 (5)
O17—H17···O2A^vii	0.82	2.47	3.230 (7)	155
O20—H20···O11^v	0.96 (5)	1.57 (5)	2.528 (3)	171 (5)

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x, y+1/2, −z; (iii) −x, y+1/2, −z+1; (iv) x−1, y, z; (v) x, y, z+1; (vi) x−1, y, z+1; (vii) −x+1, y−1/2, −z.

(V) L-lysine L-hydrogen tartrate

Crystal data

C6H15N2O2^+·C4H5O6^−	F(000) = 316
Mr = 296.28	Dx = 1.478 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1401 reflections
a = 5.1022 (11) Å	θ = 2.3–24.0°
b = 17.444 (4) Å	µ = 0.13 mm^−1
c = 7.547 (2) Å	T = 298 K
β = 97.748 (4)°	Plate, colourless
V = 665.6 (3) Å^3	0.35 × 0.25 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area detector diffractometer	1146 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ϕ and ω scan	h = −5→6
3396 measured reflections	k = −20→20
1200 independent reflections	l = −6→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.3283P] where P = (Fo^2 + 2Fc^2)/3
1200 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.25 e Å^−3
303 restraints	Δρmin = −0.19 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.060 (3)	0.2889 (10)	−0.017 (2)	0.058 (3)	0.608 (6)
O2A	−0.185 (2)	0.3939 (7)	−0.0531 (15)	0.055 (3)	0.608 (6)
N1A	−0.264 (3)	0.2161 (5)	0.1687 (15)	0.044 (3)	0.608 (6)
HA1A	−0.0915	0.2054	0.1819	0.066*	0.608 (6)
HA1B	−0.3441	0.1921	0.0723	0.066*	0.608 (6)
HA1C	−0.3319	0.2004	0.2648	0.066*	0.608 (6)
N7A	0.304 (4)	0.4380 (10)	0.8529 (13)	0.055 (3)	0.608 (6)
HA7A	0.2475	0.4862	0.8414	0.083*	0.608 (6)
HA7B	0.4665	0.4371	0.9131	0.083*	0.608 (6)
HA7C	0.1957	0.4110	0.9120	0.083*	0.608 (6)
C1A	−0.123 (2)	0.3301 (6)	0.0162 (13)	0.043 (2)	0.608 (6)
C2A	−0.3021 (16)	0.2996 (4)	0.1470 (11)	0.0406 (19)	0.608 (6)
H2A	−0.4858	0.3085	0.0944	0.049*	0.608 (6)
C3A	−0.2569 (14)	0.3413 (4)	0.3220 (10)	0.0481 (16)	0.608 (6)
H3A1	−0.3505	0.3141	0.4066	0.058*	0.608 (6)
H3A2	−0.3354	0.3918	0.3051	0.058*	0.608 (6)
C4A	0.0281 (16)	0.3506 (7)	0.4045 (12)	0.057 (2)	0.608 (6)
H4A1	0.1121	0.3008	0.4205	0.068*	0.608 (6)
H4A2	0.1231	0.3808	0.3259	0.068*	0.608 (6)
C5A	0.0372 (17)	0.3901 (6)	0.5825 (12)	0.0594 (18)	0.608 (6)
H5A1	−0.0542	0.4388	0.5648	0.071*	0.608 (6)
H5A2	−0.0574	0.3591	0.6596	0.071*	0.608 (6)
C6A	0.3080 (16)	0.4041 (6)	0.6737 (12)	0.061 (2)	0.608 (6)
H6A1	0.3995	0.4385	0.6018	0.073*	0.608 (6)
H6A2	0.4045	0.3560	0.6855	0.073*	0.608 (6)
O1B	0.102 (4)	0.2779 (13)	0.020 (3)	0.053 (4)	0.392 (6)
O2B	−0.137 (4)	0.3842 (9)	0.004 (2)	0.052 (3)	0.392 (6)
N1B	−0.315 (5)	0.2029 (8)	0.152 (2)	0.041 (3)	0.392 (6)
HB1A	−0.1730	0.1794	0.1206	0.061*	0.392 (6)
HB1B	−0.4473	0.1998	0.0626	0.061*	0.392 (6)
HB1C	−0.3618	0.1803	0.2486	0.061*	0.392 (6)
N7B	0.312 (6)	0.4550 (15)	0.8378 (16)	0.048 (4)	0.392 (6)
HB7A	0.1609	0.4437	0.8786	0.072*	0.392 (6)
HB7B	0.3685	0.5008	0.8787	0.072*	0.392 (6)
HB7C	0.4329	0.4197	0.8750	0.072*	0.392 (6)
C1B	−0.093 (4)	0.3156 (10)	0.0480 (18)	0.046 (3)	0.392 (6)
C2B	−0.252 (3)	0.2843 (8)	0.1919 (16)	0.044 (2)	0.392 (6)
H2B	−0.4163	0.3135	0.1891	0.053*	0.392 (6)
C3B	−0.089 (2)	0.2925 (6)	0.3744 (15)	0.055 (2)	0.392 (6)
H3B1	−0.1891	0.2716	0.4638	0.066*	0.392 (6)
H3B2	0.0711	0.2625	0.3768	0.066*	0.392 (6)
C4B	−0.015 (3)	0.3741 (7)	0.424 (2)	0.062 (3)	0.392 (6)
H4B1	0.0317	0.4006	0.3194	0.074*	0.392 (6)
H4B2	−0.1665	0.4001	0.4614	0.074*	0.392 (6)
C5B	0.210 (3)	0.3772 (7)	0.569 (2)	0.069 (2)	0.392 (6)
H5B1	0.3661	0.3569	0.5255	0.083*	0.392 (6)
H5B2	0.1712	0.3446	0.6667	0.083*	0.392 (6)
C6B	0.268 (3)	0.4564 (7)	0.6396 (17)	0.060 (2)	0.392 (6)
H6B1	0.4248	0.4760	0.5949	0.072*	0.392 (6)
H6B2	0.1213	0.4900	0.5985	0.072*	0.392 (6)
O11	0.3544 (5)	0.0759 (2)	1.1095 (3)	0.0403 (7)
O12	−0.0654 (5)	0.0868 (2)	0.9926 (3)	0.0376 (6)
C13	0.1708 (7)	0.0760 (2)	0.9791 (4)	0.0294 (8)
C14	0.2475 (7)	0.0643 (2)	0.7912 (5)	0.0320 (9)
H14	0.1139	0.0309	0.7255	0.038*
O15	0.4948 (6)	0.02965 (18)	0.7877 (4)	0.0363 (7)
H15	0.610 (9)	0.057 (3)	0.847 (6)	0.035 (12)*
C16	0.2275 (8)	0.1430 (3)	0.6977 (5)	0.0382 (10)
H16	0.0417	0.1590	0.6782	0.046*
O17	0.3761 (8)	0.1986 (2)	0.8029 (4)	0.0540 (9)
H17	0.285 (14)	0.232 (5)	0.860 (10)	0.10 (2)*
C18	0.3290 (9)	0.1367 (3)	0.5176 (5)	0.0430 (11)
O19	0.5278 (9)	0.1689 (3)	0.4848 (5)	0.0711 (12)
O20	0.1809 (6)	0.0936 (3)	0.4058 (4)	0.0610 (11)
H20	0.250 (16)	0.085 (6)	0.304 (11)	0.13 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.045 (6)	0.053 (5)	0.083 (7)	0.017 (4)	0.033 (6)	0.005 (4)
O2A	0.054 (5)	0.045 (4)	0.068 (6)	0.009 (3)	0.018 (4)	0.020 (3)
N1A	0.053 (7)	0.036 (5)	0.047 (4)	−0.015 (4)	0.022 (4)	−0.014 (3)
N7A	0.059 (5)	0.045 (7)	0.066 (5)	−0.028 (5)	0.027 (5)	−0.026 (5)
C1A	0.036 (4)	0.027 (5)	0.067 (4)	−0.003 (4)	0.012 (4)	−0.005 (4)
C2A	0.035 (4)	0.028 (4)	0.062 (4)	−0.004 (3)	0.019 (3)	−0.003 (3)
C3A	0.050 (3)	0.037 (3)	0.060 (4)	−0.002 (3)	0.019 (3)	−0.018 (3)
C4A	0.056 (4)	0.051 (4)	0.066 (4)	0.000 (3)	0.012 (3)	−0.016 (3)
C5A	0.056 (4)	0.054 (4)	0.070 (4)	−0.004 (3)	0.017 (3)	−0.018 (3)
C6A	0.057 (4)	0.057 (4)	0.072 (4)	−0.016 (4)	0.022 (3)	−0.023 (4)
O1B	0.035 (7)	0.050 (8)	0.078 (9)	0.004 (5)	0.027 (7)	0.000 (6)
O2B	0.047 (7)	0.034 (6)	0.081 (9)	0.004 (5)	0.024 (7)	0.005 (6)
N1B	0.036 (7)	0.034 (6)	0.055 (7)	−0.021 (5)	0.020 (5)	−0.011 (5)
N7B	0.044 (7)	0.042 (10)	0.066 (6)	−0.012 (6)	0.038 (5)	−0.010 (5)
C1B	0.039 (5)	0.030 (5)	0.073 (5)	−0.005 (4)	0.023 (4)	−0.004 (4)
C2B	0.038 (4)	0.033 (5)	0.066 (5)	−0.002 (4)	0.024 (4)	−0.009 (4)
C3B	0.050 (4)	0.044 (4)	0.069 (4)	−0.001 (4)	0.004 (4)	−0.020 (4)
C4B	0.059 (4)	0.048 (5)	0.077 (4)	0.005 (4)	0.003 (4)	−0.020 (4)
C5B	0.065 (5)	0.059 (5)	0.080 (5)	−0.001 (4)	−0.002 (4)	−0.025 (4)
C6B	0.062 (5)	0.047 (5)	0.070 (5)	0.000 (5)	0.004 (4)	−0.018 (5)
O11	0.0308 (13)	0.0699 (19)	0.0204 (12)	0.0069 (15)	0.0037 (10)	−0.0024 (14)
O12	0.0247 (13)	0.0583 (18)	0.0311 (13)	0.0024 (13)	0.0085 (10)	−0.0027 (13)
C13	0.0296 (19)	0.034 (2)	0.0248 (18)	0.0015 (16)	0.0057 (14)	−0.0003 (17)
C14	0.0254 (18)	0.047 (2)	0.0236 (18)	0.0006 (16)	0.0042 (14)	−0.0098 (16)
O15	0.0333 (15)	0.0463 (16)	0.0310 (14)	0.0035 (13)	0.0101 (11)	−0.0085 (13)
C16	0.035 (2)	0.058 (3)	0.0229 (19)	0.0136 (19)	0.0084 (15)	0.0042 (18)
O17	0.079 (2)	0.0457 (19)	0.0383 (17)	0.0004 (18)	0.0130 (16)	−0.0044 (14)
C18	0.040 (2)	0.067 (3)	0.0231 (19)	0.011 (2)	0.0074 (17)	0.005 (2)
O19	0.078 (3)	0.099 (3)	0.043 (2)	−0.017 (2)	0.0317 (18)	−0.0054 (18)
O20	0.0477 (18)	0.112 (3)	0.0252 (16)	−0.005 (2)	0.0126 (14)	−0.0116 (18)

Geometric parameters (Å, º)

O1A—C1A	1.230 (8)	N7B—HB7A	0.8900
O2A—C1A	1.252 (10)	N7B—HB7B	0.8900
N1A—C2A	1.477 (10)	N7B—HB7C	0.8900
N1A—HA1A	0.8900	C1B—C2B	1.540 (10)
N1A—HA1B	0.8900	C2B—C3B	1.515 (12)
N1A—HA1C	0.8900	C2B—H2B	0.9800
N7A—C6A	1.479 (11)	C3B—C4B	1.505 (12)
N7A—HA7A	0.8900	C3B—H3B1	0.9700
N7A—HA7B	0.8900	C3B—H3B2	0.9700
N7A—HA7C	0.8900	C4B—C5B	1.481 (12)
C1A—C2A	1.529 (9)	C4B—H4B1	0.9700
C2A—C3A	1.497 (9)	C4B—H4B2	0.9700
C2A—H2A	0.9800	C5B—C6B	1.495 (12)
C3A—C4A	1.511 (10)	C5B—H5B1	0.9700
C3A—H3A1	0.9700	C5B—H5B2	0.9700
C3A—H3A2	0.9700	C6B—H6B1	0.9700
C4A—C5A	1.505 (10)	C6B—H6B2	0.9700
C4A—H4A1	0.9700	O11—C13	1.264 (4)
C4A—H4A2	0.9700	O12—C13	1.237 (4)
C5A—C6A	1.478 (11)	C13—C14	1.535 (5)
C5A—H5A1	0.9700	C14—O15	1.402 (4)
C5A—H5A2	0.9700	C14—C16	1.540 (6)
C6A—H6A1	0.9700	C14—H14	0.9800
C6A—H6A2	0.9700	O15—H15	0.84 (5)
O1B—C1B	1.233 (10)	C16—O17	1.408 (6)
O2B—C1B	1.255 (11)	C16—C18	1.522 (5)
N1B—C2B	1.479 (10)	C16—H16	0.9800
N1B—HB1A	0.8900	O17—H17	0.89 (8)
N1B—HB1B	0.8900	C18—O19	1.214 (6)
N1B—HB1C	0.8900	C18—O20	1.295 (6)
N7B—C6B	1.483 (12)	O20—H20	0.90 (9)
O1A—C1A—O2A	126.2 (7)	C3B—C2B—C1B	109.4 (7)
O1A—C1A—C2A	117.7 (7)	N1B—C2B—H2B	109.4
O2A—C1A—C2A	116.0 (6)	C3B—C2B—H2B	109.4
N1A—C2A—C3A	112.3 (7)	C1B—C2B—H2B	109.4
N1A—C2A—C1A	109.4 (6)	C4B—C3B—C2B	113.7 (9)
C3A—C2A—C1A	111.5 (5)	C4B—C3B—H3B1	108.8
N1A—C2A—H2A	107.8	C2B—C3B—H3B1	108.8
C3A—C2A—H2A	107.8	C4B—C3B—H3B2	108.8
C1A—C2A—H2A	107.8	C2B—C3B—H3B2	108.8
C2A—C3A—C4A	116.1 (6)	H3B1—C3B—H3B2	107.7
C2A—C3A—H3A1	108.3	C5B—C4B—C3B	111.2 (9)
C4A—C3A—H3A1	108.3	C5B—C4B—H4B1	109.4
C2A—C3A—H3A2	108.3	C3B—C4B—H4B1	109.4
C4A—C3A—H3A2	108.3	C5B—C4B—H4B2	109.4
H3A1—C3A—H3A2	107.4	C3B—C4B—H4B2	109.4
C5A—C4A—C3A	109.2 (7)	H4B1—C4B—H4B2	108.0
C5A—C4A—H4A1	109.8	C4B—C5B—C6B	113.3 (9)
C3A—C4A—H4A1	109.8	C4B—C5B—H5B1	108.9
C5A—C4A—H4A2	109.8	C6B—C5B—H5B1	108.9
C3A—C4A—H4A2	109.8	C4B—C5B—H5B2	108.9
H4A1—C4A—H4A2	108.3	C6B—C5B—H5B2	108.9
C6A—C5A—C4A	113.9 (7)	H5B1—C5B—H5B2	107.7
C6A—C5A—H5A1	108.8	N7B—C6B—C5B	109.8 (11)
C4A—C5A—H5A1	108.8	N7B—C6B—H6B1	109.7
C6A—C5A—H5A2	108.8	C5B—C6B—H6B1	109.7
C4A—C5A—H5A2	108.8	N7B—C6B—H6B2	109.7
H5A1—C5A—H5A2	107.7	C5B—C6B—H6B2	109.7
C5A—C6A—N7A	111.4 (10)	H6B1—C6B—H6B2	108.2
C5A—C6A—H6A1	109.3	O12—C13—O11	124.4 (3)
N7A—C6A—H6A1	109.3	O12—C13—C14	117.9 (3)
C5A—C6A—H6A2	109.3	O11—C13—C14	117.7 (3)
N7A—C6A—H6A2	109.3	O15—C14—C13	114.6 (3)
H6A1—C6A—H6A2	108.0	O15—C14—C16	112.3 (3)
C2B—N1B—HB1A	109.5	C13—C14—C16	107.2 (3)
C2B—N1B—HB1B	109.5	O15—C14—H14	107.4
HB1A—N1B—HB1B	109.5	C13—C14—H14	107.4
C2B—N1B—HB1C	109.5	C16—C14—H14	107.4
HB1A—N1B—HB1C	109.5	C14—O15—H15	108 (3)
HB1B—N1B—HB1C	109.5	O17—C16—C18	109.3 (4)
C6B—N7B—HB7A	109.5	O17—C16—C14	111.0 (3)
C6B—N7B—HB7B	109.5	C18—C16—C14	109.6 (3)
HB7A—N7B—HB7B	109.5	O17—C16—H16	109.0
C6B—N7B—HB7C	109.5	C18—C16—H16	109.0
HB7A—N7B—HB7C	109.5	C14—C16—H16	109.0
HB7B—N7B—HB7C	109.5	C16—O17—H17	116 (5)
O1B—C1B—O2B	125.8 (9)	O19—C18—O20	124.5 (4)
O1B—C1B—C2B	116.5 (9)	O19—C18—C16	122.9 (4)
O2B—C1B—C2B	115.4 (8)	O20—C18—C16	112.6 (4)
N1B—C2B—C3B	110.7 (10)	C18—O20—H20	113 (6)
N1B—C2B—C1B	108.5 (7)
O1A—C1A—C2A—N1A	−16.2 (15)	C2B—C3B—C4B—C5B	−161.1 (14)
O2A—C1A—C2A—N1A	160.7 (10)	C3B—C4B—C5B—C6B	−172.4 (15)
O1A—C1A—C2A—C3A	108.6 (13)	C4B—C5B—C6B—N7B	135 (2)
O2A—C1A—C2A—C3A	−74.5 (11)	O12—C13—C14—O15	−161.2 (4)
N1A—C2A—C3A—C4A	75.2 (10)	O11—C13—C14—O15	20.6 (5)
C1A—C2A—C3A—C4A	−47.9 (10)	O12—C13—C14—C16	73.4 (4)
C2A—C3A—C4A—C5A	−177.4 (8)	O11—C13—C14—C16	−104.9 (4)
C3A—C4A—C5A—C6A	−178.6 (9)	O15—C14—C16—O17	−73.5 (4)
C4A—C5A—C6A—N7A	−176.0 (11)	C13—C14—C16—O17	53.3 (4)
O1B—C1B—C2B—N1B	−51 (2)	O15—C14—C16—C18	47.3 (4)
O2B—C1B—C2B—N1B	144.9 (17)	C13—C14—C16—C18	174.1 (3)
O1B—C1B—C2B—C3B	70 (2)	O17—C16—C18—O19	8.2 (6)
O2B—C1B—C2B—C3B	−94.2 (16)	C14—C16—C18—O19	−113.7 (5)
N1B—C2B—C3B—C4B	179.5 (15)	O17—C16—C18—O20	−172.0 (4)
C1B—C2B—C3B—C4B	60.0 (16)	C14—C16—C18—O20	66.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—HA1B···O12^i	0.89	2.45	2.870 (11)	110
N1A—HA1B···O17^ii	0.89	2.32	3.119 (13)	149
N1A—HA1C···O19^iii	0.89	1.97	2.862 (13)	177
N7A—HA7A···O12^iv	0.89	2.41	3.16 (2)	141
N7A—HA7B···O2A^v	0.89	1.92	2.72 (3)	149
N7A—HA7C···O1A^vi	0.89	2.32	3.10 (2)	145
N7A—HA7C···O2A^vi	0.89	2.02	2.79 (2)	145
O15—H15···O12^vii	0.84 (5)	1.93 (5)	2.736 (4)	160 (4)
O17—H17···O1A^vi	0.89 (8)	1.86 (8)	2.742 (12)	172 (7)
O20—H20···O11^i	0.90 (9)	1.63 (9)	2.533 (4)	175 (9)
N1B—HB1A···O12^i	0.89	2.00	2.753 (19)	142
N1B—HB1B···O17^ii	0.89	2.04	2.884 (19)	157
N1B—HB1C···O19^iii	0.89	1.95	2.80 (2)	160
N7B—HB7A···O2B^vi	0.89	2.16	3.02 (3)	162
N7B—HB7B···O11^viii	0.89	1.92	2.71 (2)	146
N7B—HB7C···O2B^v	0.89	2.36	3.17 (4)	151
O17—H17···O1B^vi	0.89 (8)	1.82 (8)	2.678 (18)	164 (7)

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x−1, y, z; (iv) −x, y+1/2, −z+2; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) x+1, y, z; (viii) −x+1, y+1/2, −z+2.