Bis(L-ornithinium) chloride nitrate sulfate

In the title compound, 2C₅H₁₄N₂O₂²⁺·Cl⁻·NO₃⁻·SO₄²⁻, the three anions all sit on twofold axes. The plane of the ammonioalkyl chain forms a dihedral angle of 87.8 (2)° with the carboxyl plane. In the crystal structure, the ornithine residue is linked to the sulfate anion via a strong O—H...O hydrogen bond and the structure is further stabilized by N—H...Cl and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.039
• wR factor = 0.098
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....         N3

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.420
           From the CIF: _refine_ls_abs_structure_Flack_su    0.130
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.42
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.94
           From the CIF: _reflns_number_total               1288
           Count of symmetry unique reflns         1153
           Completeness (_total/calc)            111.71%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       135
           Fraction of Friedel pairs measured     0.117
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Bis(L-ornithinium) chlorid nitrate sulfate

Crystal data

2C5H14N2O2^2+·Cl^−·NO3^−·SO4^2^−	F(000) = 488
Mr = 461.88	Dx = 1.542 Mg m^−3 Dm = 1.540 Mg m^−3 Dm measured by Flotation technique using mixture of carbon tetrachloride and xylene
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 25 reflections
a = 13.872 (5) Å	θ = 9.2–14.3°
b = 9.578 (6) Å	µ = 0.36 mm^−1
c = 9.178 (1) Å	T = 293 K
β = 125.350 (14)°	Block, colorless
V = 994.6 (7) Å^3	0.3 × 0.2 × 0.15 mm
Z = 2

Data collection

MACH3-Nonius sealed tube diffractometer	1125 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 26.9°, θmin = 2.7°
ω–2θ scans	h = −17→15
Absorption correction: ψ scan [North et al., 1968]	k = −1→12
Tmin = 0.902, Tmax = 0.999	l = −1→11
1524 measured reflections	3 standard reflections every 60 min
1288 independent reflections	intensity decay: none

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 1.3881P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
1288 reflections	Δρmax = 0.30 e Å^−3
133 parameters	Δρmin = −0.29 e Å^−3
1 restraint	Absolute structure: Flack (1983), 214 Friedels pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (13)

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
O1A	0.7128 (3)	−0.3802 (3)	0.3590 (4)	0.0386 (8)
O1B	0.5376 (2)	−0.2727 (4)	0.2054 (4)	0.0372 (7)
H1	0.507 (4)	−0.358 (6)	0.174 (6)	0.041 (14)*
C1	0.6545 (3)	−0.2753 (4)	0.3167 (5)	0.0243 (8)
C2	0.7064 (3)	−0.1302 (4)	0.3816 (5)	0.0253 (9)
H2	0.6732	−0.0891	0.4415	0.030*
N1	0.8367 (3)	−0.1465 (4)	0.5155 (4)	0.0303 (8)
H1D	0.8674	−0.1878	0.4641	0.046*
H1B	0.8507	−0.1987	0.6061	0.046*
H1C	0.8696	−0.0629	0.5559	0.046*
C3	0.6782 (3)	−0.0345 (4)	0.2295 (5)	0.0295 (9)
H3A	0.7185	0.0537	0.2796	0.035*
H3B	0.5939	−0.0158	0.1557	0.035*
C4	0.7130 (3)	−0.0921 (5)	0.1101 (5)	0.0289 (8)
H4A	0.7978	−0.1065	0.1806	0.035*
H4B	0.6747	−0.1815	0.0609	0.035*
C5	0.6766 (4)	0.0089 (5)	−0.0401 (5)	0.0378 (10)
H5A	0.5937	0.0320	−0.1001	0.045*
H5B	0.7218	0.0943	0.0099	0.045*
N2	0.6946 (3)	−0.0470 (5)	−0.1724 (4)	0.0392 (9)
H2A	0.6726	0.0167	−0.2570	0.059*
H2B	0.6514	−0.1239	−0.2217	0.059*
H2C	0.7706	−0.0674	−0.1186	0.059*
Cl1	0.5000	−0.86710 (18)	0.5000	0.0425 (4)
N3	1.0000	−0.8399 (6)	0.5000	0.0340 (12)
O1	1.0000	−0.9673 (6)	0.5000	0.0615 (16)
O2	0.9061 (4)	−0.7758 (6)	0.4130 (6)	0.0829 (16)
S1	0.5000	−0.60577 (15)	0.0000	0.0265 (3)
O3	0.5986 (3)	−0.6916 (4)	0.1386 (4)	0.0419 (8)
O4	0.4534 (2)	−0.5163 (4)	0.0774 (4)	0.0364 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0293 (15)	0.0269 (16)	0.0448 (17)	0.0000 (14)	0.0130 (13)	−0.0001 (15)
O1B	0.0244 (13)	0.0298 (17)	0.0392 (17)	−0.0022 (14)	0.0081 (12)	−0.0067 (15)
C1	0.0279 (18)	0.025 (2)	0.0208 (16)	−0.0048 (18)	0.0147 (15)	−0.0030 (16)
C2	0.0260 (16)	0.027 (2)	0.0220 (15)	0.0000 (16)	0.0131 (14)	−0.0007 (15)
N1	0.0266 (15)	0.0306 (19)	0.0211 (14)	−0.0045 (14)	0.0064 (12)	−0.0030 (13)
C3	0.0279 (17)	0.027 (2)	0.0276 (18)	0.0002 (18)	0.0128 (15)	0.0023 (18)
C4	0.0302 (17)	0.031 (2)	0.0223 (16)	−0.0014 (19)	0.0132 (14)	0.0072 (18)
C5	0.041 (2)	0.044 (3)	0.031 (2)	0.000 (2)	0.0224 (19)	0.009 (2)
N2	0.0373 (17)	0.054 (3)	0.0284 (17)	0.004 (2)	0.0204 (15)	0.0075 (18)
Cl1	0.0271 (8)	0.0399 (10)	0.0446 (9)	0.000	0.0116 (7)	0.000
N3	0.034 (3)	0.031 (3)	0.048 (3)	0.000	0.030 (3)	0.000
O1	0.065 (3)	0.035 (3)	0.102 (4)	0.000	0.058 (3)	0.000
O2	0.077 (3)	0.094 (4)	0.108 (3)	0.048 (3)	0.071 (3)	0.054 (3)
S1	0.0263 (6)	0.0247 (7)	0.0186 (6)	0.000	0.0072 (5)	0.000
O3	0.0468 (17)	0.0401 (19)	0.0228 (13)	0.0164 (16)	0.0109 (13)	0.0069 (14)
O4	0.0292 (13)	0.0411 (18)	0.0411 (15)	−0.0060 (14)	0.0215 (13)	−0.0115 (15)

Geometric parameters (Å, º)

O1A—C1	1.205 (5)	C4—H4B	0.9700
O1B—C1	1.325 (4)	C5—N2	1.474 (6)
O1B—H1	0.89 (6)	C5—H5A	0.9700
C1—C2	1.519 (5)	C5—H5B	0.9700
C2—N1	1.494 (4)	N2—H2A	0.8900
C2—C3	1.520 (5)	N2—H2B	0.8900
C2—H2	0.9800	N2—H2C	0.8900
N1—H1D	0.8900	N3—O1	1.220 (8)
N1—H1B	0.8900	N3—O2	1.228 (5)
N1—H1C	0.8900	N3—O2^i	1.228 (5)
C3—C4	1.533 (5)	S1—O3^ii	1.466 (3)
C3—H3A	0.9700	S1—O3	1.466 (3)
C3—H3B	0.9700	S1—O4	1.479 (3)
C4—C5	1.512 (6)	S1—O4^ii	1.479 (3)
C4—H4A	0.9700
C1—O1B—H1	112 (3)	C5—C4—H4B	109.6
O1A—C1—O1B	123.9 (4)	C3—C4—H4B	109.6
O1A—C1—C2	124.0 (3)	H4A—C4—H4B	108.1
O1B—C1—C2	112.1 (3)	N2—C5—C4	113.1 (4)
N1—C2—C1	107.5 (3)	N2—C5—H5A	109.0
N1—C2—C3	111.4 (3)	C4—C5—H5A	109.0
C1—C2—C3	112.3 (3)	N2—C5—H5B	109.0
N1—C2—H2	108.5	C4—C5—H5B	109.0
C1—C2—H2	108.5	H5A—C5—H5B	107.8
C3—C2—H2	108.5	C5—N2—H2A	109.5
C2—N1—H1D	109.5	C5—N2—H2B	109.5
C2—N1—H1B	109.5	H2A—N2—H2B	109.5
H1D—N1—H1B	109.5	C5—N2—H2C	109.5
C2—N1—H1C	109.5	H2A—N2—H2C	109.5
H1D—N1—H1C	109.5	H2B—N2—H2C	109.5
H1B—N1—H1C	109.5	O1—N3—O2	120.0 (4)
C2—C3—C4	114.8 (3)	O1—N3—O2^i	120.0 (4)
C2—C3—H3A	108.6	O2—N3—O2^i	119.9 (7)
C4—C3—H3A	108.6	O3^ii—S1—O3	111.8 (3)
C2—C3—H3B	108.6	O3^ii—S1—O4	107.10 (17)
C4—C3—H3B	108.6	O3—S1—O4	110.81 (17)
H3A—C3—H3B	107.5	O3^ii—S1—O4^ii	110.81 (17)
C5—C4—C3	110.1 (4)	O3—S1—O4^ii	107.10 (17)
C5—C4—H4A	109.6	O4—S1—O4^ii	109.2 (3)
C3—C4—H4A	109.6
O1A—C1—C2—N1	−5.3 (5)	N1—C2—C3—C4	66.7 (4)
O1B—C1—C2—N1	175.9 (3)	C1—C2—C3—C4	−53.9 (4)
O1A—C1—C2—C3	117.5 (4)	C2—C3—C4—C5	177.8 (3)
O1B—C1—C2—C3	−61.3 (4)	C3—C4—C5—N2	−173.2 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1···O4	0.89 (6)	1.69 (6)	2.569 (5)	167 (5)
N1—H1B···O3^iii	0.89	2.02	2.788 (4)	144
N1—H1C···O1^iv	0.89	2.33	2.911 (5)	123
N1—H1C···O1A^iii	0.89	2.45	3.036 (5)	124
N1—H1D···Cl1^v	0.89	2.40	3.160 (4)	144
N2—H2A···Cl1^vi	0.89	2.40	3.147 (4)	141
N2—H2B···O2^vii	0.89	2.05	2.839 (6)	147
N2—H2C···O4^v	0.89	2.15	2.951 (5)	149
N2—H2C···O3^vii	0.89	2.26	3.036 (5)	145

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