L-Kynureninium sulfate dihydrate

In the structure of the title compound, 2-(3-ammonio-3-carboxy­propanoyl)-1-anilinium sulfate dihydrate, C₁₀H₁₄N₂O₃²⁺·SO₄^2-·2H₂O, the two amino groups are proton­ated. The mol­ecule has a trans planar zigzag carbon-skeletal conformation elongated nearly in the benzene ring plane. The two amino and the carboxyl groups are located on the same side of the mol­ecule. The crystal structure is stabilized by intermolecular hydrogen bonds involving the water mol­ecules and the sulfate ion.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); data reduction: TEXSAN PROCESS (Molecular Structure Corporation, 1999b); program(s) used to solve structure: SIR88 (Burla et al., 1989) and DIRDIF (Beurskens et al., 1994); program(s) used to refine structure: TEXSAN LS; software used to prepare material for publication: TEXSAN.

L-Kynulenine sulfate dihydrate

Crystal data

C10H14N2O3^2+·SO4^2^−·2H2O	Dx = 1.534 Mg m^−3
Mr = 342.32	Mo Kα radiation, λ = 0.71069 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 11.353 (5) Å	θ = 10.3–14.5°
b = 22.134 (5) Å	µ = 0.27 mm^−1
c = 5.897 (7) Å	T = 296 K
V = 1481 (1) Å^3	Needle, light yellow
Z = 4	0.50 × 0.10 × 0.05 mm

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.058
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −14→14
Tmin = 0.972, Tmax = 0.998	k = −28→28
4128 measured reflections	l = −7→7
2072 independent reflections	3 standard reflections every 150 reflections
1088 reflections with F^2 > 2σ(F^2)	intensity decay: 0.1%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.06100(Max(Fo^2,0) + 2Fc^2)/3)^2]
wR(F^2) = 0.163	(Δ/σ)max = 0.004
S = 1.15	Δρmax = 0.81 e Å^−3
2071 reflections	Δρmin = −0.90 e Å^−3
200 parameters

Special details

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted

R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are

based on F. The threshold expression of F² > 2.0 σ(F²) is used only

for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
S	0.1157 (1)	0.10868 (7)	0.0645 (3)	0.0328 (4)
O1	0.3674 (4)	0.0657 (2)	0.4722 (7)	0.044 (1)
O2	0.5063 (4)	0.2318 (2)	0.9046 (9)	0.053 (1)
O3	0.3324 (4)	0.2748 (2)	0.8345 (9)	0.053 (1)
O4	0.1080 (4)	0.1037 (2)	0.3108 (7)	0.042 (1)
O5	0.1170 (5)	0.1721 (2)	−0.0005 (8)	0.057 (1)
O6	0.0108 (4)	0.0798 (2)	−0.0396 (9)	0.059 (2)
O7	0.2182 (4)	0.0787 (2)	−0.0293 (9)	0.053 (2)
O8	0.7406 (5)	0.2143 (2)	0.6611 (9)	0.065 (2)
O9	0.9181 (8)	0.1402 (5)	0.588 (1)	0.168 (4)
N1	0.3908 (5)	−0.0003 (2)	0.0929 (8)	0.029 (1)
N2	0.2493 (4)	0.1814 (2)	0.6008 (9)	0.030 (1)
C1	0.5284 (5)	0.0801 (2)	0.223 (1)	0.029 (1)
C2	0.5027 (5)	0.0335 (2)	0.071 (1)	0.028 (1)
C3	0.5777 (6)	0.0176 (3)	−0.098 (1)	0.039 (2)
C4	0.6861 (6)	0.0476 (3)	−0.118 (1)	0.046 (2)
C5	0.7152 (5)	0.0921 (3)	0.031 (1)	0.045 (2)
C6	0.6368 (5)	0.1092 (3)	0.196 (1)	0.037 (2)
C7	0.4444 (5)	0.0992 (3)	0.406 (1)	0.031 (1)
C8	0.4585 (6)	0.1615 (3)	0.503 (1)	0.036 (2)
C9	0.3688 (5)	0.1759 (2)	0.6883 (10)	0.027 (1)
C10	0.4004 (6)	0.2341 (3)	0.8165 (10)	0.032 (1)
H1	0.5594	−0.0150	−0.1918	0.0440*
H2	0.7419	0.0347	−0.2218	0.0591*
H3	0.7892	0.1112	0.0127	0.0633*
H4	0.6569	0.1415	0.2949	0.0373*
H5	0.5359	0.1668	0.5558	0.0397*
H6	0.4464	0.1894	0.3760	0.0397*
H7	0.3703	0.1434	0.7935	0.0280*
H8	0.5064	0.2873	0.8871	0.0610*
H9	0.1954	0.1671	0.7149	0.0327*
H10	0.2327	0.2230	0.5731	0.0327*
H11	0.2405	0.1588	0.4685	0.0327*
H12	0.3892	−0.0197	0.2445	0.0415*
H13	0.3264	0.0253	0.0833	0.0415*
H14	0.3874	−0.0317	−0.0147	0.0415*
H15	0.6970	0.2428	0.7383	0.0610*
H16	0.8016	0.2228	0.7087	0.0610*
H17	0.9535	0.1831	0.5596	0.0610*
H18	0.9376	0.1241	0.7491	0.0610*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0401 (9)	0.0300 (7)	0.0283 (7)	0.0087 (8)	0.0104 (8)	0.0074 (7)
O1	0.046 (3)	0.036 (2)	0.048 (3)	−0.013 (2)	0.018 (3)	−0.012 (2)
O2	0.049 (2)	0.038 (2)	0.072 (4)	0.006 (2)	−0.016 (3)	−0.013 (3)
O3	0.052 (3)	0.040 (3)	0.068 (3)	0.009 (2)	−0.014 (3)	−0.023 (3)
O4	0.052 (3)	0.042 (2)	0.031 (1)	−0.014 (3)	0.010 (3)	0.003 (2)
O5	0.075 (3)	0.030 (2)	0.065 (3)	0.017 (3)	0.041 (3)	0.011 (2)
O6	0.056 (3)	0.077 (4)	0.045 (3)	−0.015 (3)	−0.011 (3)	−0.007 (3)
O7	0.054 (3)	0.044 (3)	0.060 (4)	0.031 (2)	0.028 (3)	0.015 (3)
O8	0.068 (4)	0.059 (3)	0.069 (4)	0.017 (3)	0.009 (3)	0.012 (3)
O9	0.173 (9)	0.25 (1)	0.076 (5)	0.159 (8)	0.029 (6)	0.063 (7)
N1	0.033 (2)	0.025 (2)	0.029 (2)	−0.001 (2)	0.001 (3)	−0.006 (2)
N2	0.033 (2)	0.023 (2)	0.034 (3)	−0.008 (2)	0.016 (2)	−0.007 (2)
C1	0.030 (3)	0.027 (3)	0.031 (3)	0.000 (2)	−0.002 (2)	−0.002 (2)
C2	0.030 (3)	0.026 (3)	0.029 (3)	−0.001 (2)	−0.003 (3)	0.004 (2)
C3	0.041 (3)	0.041 (4)	0.036 (4)	−0.002 (3)	0.006 (3)	−0.014 (3)
C4	0.038 (3)	0.053 (5)	0.048 (5)	0.001 (3)	0.022 (3)	−0.008 (3)
C5	0.025 (3)	0.052 (4)	0.057 (5)	−0.006 (3)	0.012 (3)	−0.006 (3)
C6	0.033 (3)	0.034 (3)	0.042 (3)	−0.006 (3)	0.002 (3)	−0.005 (3)
C7	0.033 (3)	0.028 (3)	0.032 (3)	0.004 (2)	−0.001 (2)	−0.004 (2)
C8	0.033 (3)	0.032 (3)	0.043 (4)	−0.004 (3)	0.015 (3)	−0.016 (3)
C9	0.037 (3)	0.018 (2)	0.027 (3)	−0.001 (3)	0.008 (2)	0.006 (2)
C10	0.046 (3)	0.029 (3)	0.022 (3)	−0.009 (2)	0.007 (3)	−0.004 (2)

Geometric parameters (Å, º)

S—O4	1.461 (4)	C1—C6	1.397 (9)
S—O5	1.455 (5)	C1—C7	1.500 (9)
S—O6	1.486 (5)	C2—C3	1.357 (9)
S—O7	1.447 (5)	C3—C4	1.405 (10)
O1—C7	1.212 (8)	C4—C5	1.36 (1)
O2—C10	1.309 (8)	C5—C6	1.374 (9)
O3—C10	1.189 (8)	C7—C8	1.503 (9)
N1—C2	1.480 (8)	C8—C9	1.527 (9)
N2—C9	1.458 (8)	C9—C10	1.537 (9)
C1—C2	1.398 (8)
O4—S—O5	109.8 (3)	C3—C4—C5	119.9 (6)
O4—S—O6	109.3 (3)	C4—C5—C6	120.1 (6)
O4—S—O7	113.1 (3)	C1—C6—C5	121.7 (7)
O5—S—O6	108.3 (4)	O1—C7—C1	121.3 (5)
O5—S—O7	109.4 (3)	O1—C7—C8	121.1 (6)
O6—S—O7	106.8 (3)	C1—C7—C8	117.6 (5)
C2—C1—C6	116.8 (6)	C7—C8—C9	113.1 (5)
C2—C1—C7	122.3 (6)	N2—C9—C8	112.6 (5)
C6—C1—C7	120.9 (6)	N2—C9—C10	108.8 (5)
N1—C2—C1	119.8 (6)	C8—C9—C10	111.9 (5)
N1—C2—C3	118.2 (5)	O2—C10—O3	126.1 (6)
C1—C2—C3	122.0 (6)	O2—C10—C9	112.2 (6)
C2—C3—C4	119.5 (6)	O3—C10—C9	121.7 (6)
O1—C7—C1—C2	21.2 (10)	C1—C6—C5—C4	2 (1)
O1—C7—C1—C6	−159.6 (7)	C1—C7—C8—C9	−179.6 (5)
O1—C7—C8—C9	0.7 (9)	C2—C1—C6—C5	−1 (1)
O2—C10—C9—N2	178.6 (5)	C2—C1—C7—C8	−158.4 (6)
O2—C10—C9—C8	−56.5 (7)	C2—C3—C4—C5	−0 (1)
O3—C10—C9—N2	0.4 (8)	C3—C2—C1—C6	−1.1 (9)
O3—C10—C9—C8	125.3 (7)	C3—C2—C1—C7	178.1 (6)
N1—C2—C1—C6	178.6 (5)	C3—C4—C5—C6	−1 (1)
N1—C2—C1—C7	−2.2 (9)	C5—C6—C1—C7	179.7 (6)
N1—C2—C3—C4	−177.9 (6)	C6—C1—C7—C8	20.8 (9)
N2—C9—C8—C7	−68.7 (7)	C7—C8—C9—C10	168.4 (5)
C1—C2—C3—C4	1 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O1	0.991	2.334	2.688 (7)	99.928
N2—H11···O1	0.929	2.514	2.992 (7)	112.188
N2—H10···O3	0.949	2.225	2.655 (7)	106.467
N1—H13···O7	0.929	1.826	2.723 (7)	161.424
N1—H12···O6^i	0.991	2.162	3.004 (8)	141.845
N1—H12···O7^i	0.991	2.234	3.086 (7)	143.381
N1—H14···O4^ii	0.939	1.893	2.822 (6)	169.482
N2—H11···O4	0.929	2.150	2.906 (7)	137.703
N2—H9···O5^iii	0.964	1.903	2.799 (8)	153.490
N2—H9···O7^iii	0.964	2.488	3.178 (8)	128.416
N1—H13···O1^ii	0.929	3.055	3.345 (7)	100.033

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