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In the title compound, C5H14N2O22+·SO42−·H2O, the ornithinium cation forms a strong O—H...O hydrogen bond with the sulfate anion. One backbone conformation angle is in an eclipsed conformation, while the other two are in a transtrans staggered conformation. All the amino and carboxyl­ate groups and the sulfate anions are involved in hydrogen bonding. The amino groups are also involved in a three-centred hydrogen bond with the O atoms of the sulfate anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026108/hg6090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026108/hg6090Isup2.hkl
Contains datablock I

CCDC reference: 255926

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.059
  • wR factor = 0.171
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ? PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors for S
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. HW2 .. 2.03 Ang.
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
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 25.00 From the CIF: _reflns_number_total 1172 Count of symmetry unique reflns 1176 Completeness (_total/calc) 99.66% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

L-ornithinium sulfate monohydrate top
Crystal data top
C5H14N2O22+·SO42·H2OF(000) = 528
Mr = 248.26Dx = 1.478 Mg m3
Dm = 1.475 (5) Mg m3
Dm measured by flotation, using a mixture of CCl4 and xylene
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.1589 (2) Åθ = 11.3–14.2°
b = 9.682 (6) ŵ = 0.31 mm1
c = 18.714 (6) ÅT = 293 K
V = 1115.9 (8) Å3Needle, colourless
Z = 40.3 × 0.3 × 0.2 mm
Data collection top
Nonius MACH 3
diffractometer
1043 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25°, θmin = 2.2°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 111
Tmin = 0.911, Tmax = 0.940l = 122
1399 measured reflections3 standard reflections every 60 min
1172 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.112P)2 + 1.3829P]
where P = (Fo2 + 2Fc2)/3
1172 reflections(Δ/σ)max = 0.005
137 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.37 e Å3
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.

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 (Å2) top
xyzUiso*/Ueq
S0.8970 (2)1.08983 (15)0.38083 (7)0.0351 (4)
O10.9854 (11)0.9625 (6)0.4097 (3)0.0727 (17)
O21.0139 (15)1.1997 (7)0.4173 (4)0.115 (3)
O30.6680 (9)1.0937 (11)0.3919 (3)0.113 (3)
O40.9426 (8)1.0964 (5)0.3028 (2)0.0601 (13)
O1B0.2449 (8)0.7737 (5)0.3687 (2)0.0521 (12)
H10.12940.81530.36540.078*
O1A0.3372 (7)0.8776 (4)0.2665 (2)0.0484 (11)
C10.3527 (10)0.7842 (5)0.3081 (3)0.0348 (12)
C20.5051 (9)0.6633 (5)0.2972 (3)0.0339 (12)
H20.42320.57700.30180.041*
N10.5922 (8)0.6736 (5)0.2243 (2)0.0386 (11)
H1A0.68230.60340.21620.058*
H1B0.66370.75290.21950.058*
H1C0.48340.67070.19300.058*
C30.6955 (10)0.6628 (6)0.3514 (3)0.0445 (15)
H3A0.83130.65450.32550.053*
H3B0.69740.75020.37670.053*
C40.6799 (10)0.5474 (7)0.4048 (3)0.0402 (14)
H4A0.67390.45990.37970.048*
H4B0.54670.55730.43200.048*
C50.8739 (10)0.5466 (6)0.4563 (3)0.0387 (13)
H5A1.00810.55140.42920.046*
H5B0.86680.62690.48720.046*
N20.8728 (8)0.4213 (5)0.4996 (2)0.0411 (11)
H2A0.98610.42220.52910.062*
H2B0.88090.34780.47120.062*
H2C0.75060.41770.52490.062*
OW0.8602 (8)0.9016 (5)0.2011 (3)0.0576 (12)
HW10.89240.94920.23980.050*
HW20.96100.84200.21060.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0301 (6)0.0376 (7)0.0377 (7)0.0008 (6)0.0022 (6)0.0016 (6)
O10.091 (5)0.066 (3)0.060 (3)0.023 (3)0.008 (3)0.007 (3)
O20.122 (7)0.079 (4)0.143 (6)0.001 (4)0.041 (6)0.062 (4)
O30.036 (3)0.242 (10)0.061 (3)0.025 (5)0.012 (2)0.048 (5)
O40.059 (3)0.071 (3)0.050 (2)0.009 (3)0.012 (2)0.001 (2)
O1B0.050 (3)0.053 (3)0.054 (3)0.010 (2)0.013 (2)0.012 (2)
O1A0.045 (2)0.038 (2)0.062 (3)0.0102 (19)0.004 (2)0.014 (2)
C10.034 (3)0.031 (2)0.040 (3)0.002 (2)0.002 (2)0.000 (2)
C20.031 (3)0.022 (2)0.050 (3)0.002 (2)0.010 (3)0.004 (2)
N10.033 (2)0.035 (2)0.048 (2)0.007 (2)0.006 (2)0.007 (2)
C30.041 (3)0.034 (3)0.059 (4)0.003 (3)0.020 (3)0.004 (3)
C40.030 (3)0.055 (3)0.036 (3)0.002 (3)0.006 (2)0.006 (3)
C50.038 (3)0.047 (3)0.032 (2)0.002 (3)0.003 (3)0.000 (2)
N20.035 (2)0.054 (3)0.034 (2)0.000 (3)0.006 (2)0.001 (2)
OW0.047 (2)0.051 (2)0.075 (3)0.003 (2)0.003 (2)0.006 (2)
Geometric parameters (Å, º) top
S—O31.426 (6)C3—C41.502 (8)
S—O21.455 (7)C3—H3A0.9700
S—O11.452 (5)C3—H3B0.9700
S—O41.489 (5)C4—C51.535 (8)
O1B—C11.319 (7)C4—H4A0.9700
O1B—H10.8200C4—H4B0.9700
O1A—C11.197 (7)C5—N21.458 (7)
C1—C21.514 (8)C5—H5A0.9700
C2—N11.469 (7)C5—H5B0.9700
C2—C31.550 (8)N2—H2A0.8900
C2—H20.9800N2—H2B0.8900
N1—H1A0.8900N2—H2C0.8900
N1—H1B0.8900OW—HW10.881
N1—H1C0.8900OW—HW20.866
O3—S—O2113.7 (6)C2—C3—H3A109.0
O3—S—O1109.8 (5)C4—C3—H3B109.0
O2—S—O1105.1 (4)C2—C3—H3B109.0
O3—S—O4109.2 (3)H3A—C3—H3B107.8
O2—S—O4109.6 (4)C3—C4—C5111.9 (5)
O1—S—O4109.3 (3)C3—C4—H4A109.2
C1—O1B—H1109.5C5—C4—H4A109.2
O1A—C1—O1B125.3 (6)C3—C4—H4B109.2
O1A—C1—C2123.1 (5)C5—C4—H4B109.2
O1B—C1—C2111.6 (5)H4A—C4—H4B107.9
N1—C2—C1107.4 (4)N2—C5—C4110.4 (5)
N1—C2—C3109.4 (5)N2—C5—H5A109.6
C1—C2—C3112.5 (5)C4—C5—H5A109.6
N1—C2—H2109.2N2—C5—H5B109.6
C1—C2—H2109.2C4—C5—H5B109.6
C3—C2—H2109.2H5A—C5—H5B108.1
C2—N1—H1A109.5C5—N2—H2A109.5
C2—N1—H1B109.5C5—N2—H2B109.5
H1A—N1—H1B109.5H2A—N2—H2B109.5
C2—N1—H1C109.5C5—N2—H2C109.5
H1A—N1—H1C109.5H2A—N2—H2C109.5
H1B—N1—H1C109.5H2B—N2—H2C109.5
C4—C3—C2112.9 (5)HW1—OW—HW291.1
C4—C3—H3A109.0
O1A—C1—C2—N19.3 (8)N1—C2—C3—C4130.3 (5)
O1B—C1—C2—N1171.8 (5)C1—C2—C3—C4110.4 (6)
O1A—C1—C2—C3111.1 (6)C2—C3—C4—C5178.2 (5)
O1B—C1—C2—C367.8 (7)C3—C4—C5—N2170.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1···O1i0.821.872.546 (7)139
N1—H1A···O1Aii0.892.212.903 (6)134
N1—H1A···O4iii0.892.343.003 (7)132
N1—H1B···OW0.891.912.790 (7)169
N1—H1C···O3ii0.891.992.810 (7)153
N2—H2A···O3iv0.891.862.729 (7)165
N2—H2B···O2v0.891.942.781 (8)158
N2—H2C···O2vi0.892.142.945 (10)150
N2—H2C···O1vi0.892.353.136 (8)148
OW—HW1···O40.881.882.726 (7)162
OW—HW2···O4iii0.872.463.195 (7)143
OW—HW2···O1Avii0.872.573.191 (7)130
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+1/2; (iii) x+2, y1/2, z+1/2; (iv) x+1/2, y+3/2, z+1; (v) x, y1, z; (vi) x1/2, y+3/2, z+1; (vii) x+1, y, z.
 

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