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The formation of the title compound, (S)-2-ammonio-1-butanol (2R,3R)-tartrate, C4H12NO+·C4H5O6-, the (S)-2-amino-1-butanol mol­ecule is converted to a cationic form containing a positively charged amino group, and the tartaric acid mol­ecule to a mono- or half-ionized tartrate anion. The structure is stabilized by a three-dimensional network of hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008767/gh6018sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008767/gh6018Isup2.hkl
Contains datablock I

CCDC reference: 270326

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.083
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.93 From the CIF: _reflns_number_total 1551 Count of symmetry unique reflns 1550 Completeness (_total/calc) 100.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(S)-2-amino-1-butanol (2R,3R)-tartrate top
Crystal data top
C4H12NO+·C4H5O6F(000) = 512
Mr = 239.23Dx = 1.433 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3501 reflections
a = 7.2959 (7) Åθ = 2.5–27.9°
b = 9.4843 (9) ŵ = 0.13 mm1
c = 16.0204 (16) ÅT = 293 K
V = 1108.56 (19) Å3Block, colourless
Z = 40.32 × 0.28 × 0.26 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1551 independent reflections
Radiation source: fine-focus sealed tube1441 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 99
Tmin = 0.956, Tmax = 0.968k = 1212
7492 measured reflectionsl = 2112
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.0747P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1551 reflectionsΔρmax = 0.18 e Å3
171 parametersΔρmin = 0.19 e Å3
7 restraintsAbsolute structure: Friedel pairs were merged; the hand was established by use of a pure (2R,3R)tartaric acid component.
Primary atom site location: structure-invariant direct methods
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
O10.7237 (2)0.46675 (13)0.95856 (8)0.0430 (3)
O20.86184 (19)0.31069 (15)1.04027 (7)0.0426 (3)
H20.803 (3)0.350 (3)1.0806 (13)0.064*
O30.83865 (17)0.33572 (13)0.81953 (7)0.0362 (3)
H30.909 (3)0.389 (2)0.7916 (14)0.054*
O40.72321 (19)0.08494 (14)0.89742 (11)0.0514 (4)
H40.657 (4)0.147 (2)0.9162 (18)0.077*
O51.19287 (16)0.08658 (13)0.83771 (7)0.0345 (3)
O60.94647 (18)0.01134 (14)0.78128 (8)0.0415 (3)
C10.8234 (2)0.36644 (16)0.96787 (10)0.0285 (3)
C20.9190 (2)0.29293 (15)0.89484 (9)0.0271 (3)
H2A1.04850.32030.89450.033*
C30.9062 (2)0.13169 (16)0.90305 (10)0.0284 (3)
H3A0.95570.10390.95750.034*
C41.0217 (2)0.06315 (16)0.83462 (10)0.0277 (3)
C50.4666 (3)0.29497 (17)0.64838 (11)0.0368 (4)
H5A0.55030.36800.62980.044*
H5B0.38160.27440.60340.044*
C60.5719 (2)0.16340 (15)0.67218 (9)0.0289 (3)
H60.64790.18490.72100.035*
C70.6958 (3)0.10806 (19)0.60294 (12)0.0402 (4)
H7A0.73010.01160.61560.048*
H7B0.62800.10740.55090.048*
C80.8674 (3)0.1948 (3)0.59189 (15)0.0547 (5)
H8A0.83490.28790.57350.082*
H8B0.94500.15100.55100.082*
H8C0.93130.20090.64410.082*
N10.4361 (2)0.05364 (15)0.69611 (9)0.0329 (3)
H1A0.357 (3)0.085 (2)0.7347 (11)0.048 (6)*
H1B0.494 (3)0.0194 (17)0.7180 (12)0.043 (6)*
H1C0.365 (2)0.024 (2)0.6543 (10)0.036 (5)*
O70.36965 (18)0.34047 (13)0.72031 (9)0.0399 (3)
H70.280 (2)0.395 (2)0.7049 (15)0.056 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0552 (8)0.0359 (6)0.0380 (6)0.0160 (6)0.0062 (6)0.0002 (5)
O20.0458 (7)0.0553 (8)0.0268 (6)0.0203 (7)0.0003 (5)0.0058 (5)
O30.0395 (6)0.0401 (6)0.0290 (6)0.0010 (6)0.0035 (5)0.0060 (5)
O40.0325 (7)0.0368 (7)0.0849 (11)0.0090 (6)0.0227 (7)0.0090 (7)
O50.0271 (5)0.0461 (7)0.0302 (6)0.0025 (5)0.0048 (4)0.0113 (5)
O60.0335 (6)0.0518 (7)0.0392 (6)0.0034 (6)0.0015 (5)0.0175 (6)
C10.0280 (7)0.0279 (6)0.0295 (7)0.0026 (6)0.0020 (6)0.0048 (6)
C20.0259 (7)0.0266 (6)0.0289 (7)0.0012 (6)0.0052 (6)0.0010 (6)
C30.0275 (7)0.0267 (6)0.0310 (7)0.0008 (6)0.0076 (6)0.0005 (6)
C40.0285 (7)0.0277 (6)0.0270 (7)0.0006 (6)0.0027 (6)0.0024 (6)
C50.0444 (9)0.0287 (7)0.0372 (8)0.0062 (7)0.0028 (7)0.0023 (6)
C60.0321 (7)0.0256 (7)0.0290 (7)0.0004 (6)0.0004 (6)0.0013 (6)
C70.0444 (9)0.0351 (8)0.0410 (9)0.0022 (8)0.0114 (8)0.0042 (7)
C80.0453 (11)0.0643 (13)0.0546 (12)0.0041 (11)0.0165 (9)0.0001 (10)
N10.0377 (7)0.0272 (6)0.0338 (7)0.0009 (6)0.0053 (6)0.0019 (5)
O70.0391 (6)0.0347 (6)0.0461 (7)0.0089 (6)0.0035 (6)0.0026 (5)
Geometric parameters (Å, º) top
O1—C11.207 (2)C5—H5A0.9700
O2—C11.305 (2)C5—H5B0.9700
O2—H20.861 (10)C6—N11.487 (2)
O3—C21.4015 (19)C6—C71.524 (2)
O3—H30.853 (10)C6—H60.9800
O4—C31.410 (2)C7—C81.508 (3)
O4—H40.824 (10)C7—H7A0.9700
O5—C41.269 (2)C7—H7B0.9700
O6—C41.237 (2)C8—H8A0.9600
C1—C21.530 (2)C8—H8B0.9600
C2—C31.538 (2)C8—H8C0.9600
C2—H2A0.9800N1—H1A0.893 (10)
C3—C41.528 (2)N1—H1B0.886 (10)
C3—H3A0.9800N1—H1C0.890 (10)
C5—O71.419 (2)O7—H70.866 (10)
C5—C61.514 (2)
C1—O2—H2113 (2)H5A—C5—H5B108.5
C2—O3—H3111.8 (17)N1—C6—C5107.67 (13)
C3—O4—H4108 (2)N1—C6—C7109.98 (13)
O1—C1—O2123.97 (14)C5—C6—C7113.68 (14)
O1—C1—C2122.64 (14)N1—C6—H6108.5
O2—C1—C2113.39 (13)C5—C6—H6108.5
O3—C2—C1109.60 (12)C7—C6—H6108.5
O3—C2—C3109.65 (13)C8—C7—C6112.93 (16)
C1—C2—C3111.10 (13)C8—C7—H7A109.0
O3—C2—H2A108.8C6—C7—H7A109.0
C1—C2—H2A108.8C8—C7—H7B109.0
C3—C2—H2A108.8C6—C7—H7B109.0
O4—C3—C4110.03 (13)H7A—C7—H7B107.8
O4—C3—C2111.40 (13)C7—C8—H8A109.5
C4—C3—C2109.16 (13)C7—C8—H8B109.5
O4—C3—H3A108.7H8A—C8—H8B109.5
C4—C3—H3A108.7C7—C8—H8C109.5
C2—C3—H3A108.7H8A—C8—H8C109.5
O6—C4—O5124.29 (15)H8B—C8—H8C109.5
O6—C4—C3119.60 (14)C6—N1—H1A112.1 (14)
O5—C4—C3116.11 (14)C6—N1—H1B109.2 (15)
O7—C5—C6107.40 (14)H1A—N1—H1B107 (2)
O7—C5—H5A110.2C6—N1—H1C114.3 (13)
C6—C5—H5A110.2H1A—N1—H1C104.6 (19)
O7—C5—H5B110.2H1B—N1—H1C109 (2)
C6—C5—H5B110.2C5—O7—H7108.9 (17)
O1—C1—C2—O314.5 (2)O4—C3—C4—O65.5 (2)
O2—C1—C2—O3166.02 (13)C2—C3—C4—O6117.06 (17)
O1—C1—C2—C3135.85 (16)O4—C3—C4—O5173.70 (15)
O2—C1—C2—C344.69 (19)C2—C3—C4—O563.76 (19)
O3—C2—C3—O456.58 (17)O7—C5—C6—N162.55 (17)
C1—C2—C3—O464.72 (18)O7—C5—C6—C7175.36 (15)
O3—C2—C3—C465.13 (16)N1—C6—C7—C8163.94 (16)
C1—C2—C3—C4173.56 (12)C5—C6—C7—C875.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O4i0.87 (1)2.44 (2)3.0647 (19)130 (2)
O7—H7···O6i0.87 (1)1.89 (1)2.7010 (18)155 (2)
N1—H1C···O3ii0.89 (1)2.36 (2)2.8901 (19)118 (2)
N1—H1C···O1ii0.89 (1)2.00 (1)2.860 (2)163 (2)
N1—H1B···O7ii0.89 (1)1.93 (1)2.809 (2)171 (2)
N1—H1A···O5iii0.89 (1)2.04 (1)2.8970 (18)160 (2)
O4—H4···O2iv0.82 (1)2.30 (2)2.9879 (19)142 (3)
O3—H3···O6v0.85 (1)1.83 (1)2.6777 (18)172 (2)
O2—H2···O5iv0.86 (1)1.65 (1)2.5081 (17)175 (3)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2; (iii) x1, y, z; (iv) x1/2, y+1/2, z+2; (v) x+2, y+1/2, z+3/2.
 

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