(S)-2-Ammoniobutan-1-ol (2R,3R)-tartrate

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.

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

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Computing details

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

Crystal data

C4H12NO^+·C4H5O6^−	F(000) = 512
Mr = 239.23	Dx = 1.433 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3501 reflections
a = 7.2959 (7) Å	θ = 2.5–27.9°
b = 9.4843 (9) Å	µ = 0.13 mm^−1
c = 16.0204 (16) Å	T = 293 K
V = 1108.56 (19) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1551 independent reflections
Radiation source: fine-focus sealed tube	1441 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.956, Tmax = 0.968	k = −12→12
7492 measured reflections	l = −21→12

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.0747P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1551 reflections	Δρmax = 0.18 e Å^−3
171 parameters	Δρmin = −0.19 e Å^−3
7 restraints	Absolute 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

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	0.7237 (2)	0.46675 (13)	0.95856 (8)	0.0430 (3)
O2	0.86184 (19)	0.31069 (15)	1.04027 (7)	0.0426 (3)
H2	0.803 (3)	0.350 (3)	1.0806 (13)	0.064*
O3	0.83865 (17)	0.33572 (13)	0.81953 (7)	0.0362 (3)
H3	0.909 (3)	0.389 (2)	0.7916 (14)	0.054*
O4	0.72321 (19)	0.08494 (14)	0.89742 (11)	0.0514 (4)
H4	0.657 (4)	0.147 (2)	0.9162 (18)	0.077*
O5	1.19287 (16)	0.08658 (13)	0.83771 (7)	0.0345 (3)
O6	0.94647 (18)	−0.01134 (14)	0.78128 (8)	0.0415 (3)
C1	0.8234 (2)	0.36644 (16)	0.96787 (10)	0.0285 (3)
C2	0.9190 (2)	0.29293 (15)	0.89484 (9)	0.0271 (3)
H2A	1.0485	0.3203	0.8945	0.033*
C3	0.9062 (2)	0.13169 (16)	0.90305 (10)	0.0284 (3)
H3A	0.9557	0.1039	0.9575	0.034*
C4	1.0217 (2)	0.06315 (16)	0.83462 (10)	0.0277 (3)
C5	0.4666 (3)	0.29497 (17)	0.64838 (11)	0.0368 (4)
H5A	0.5503	0.3680	0.6298	0.044*
H5B	0.3816	0.2744	0.6034	0.044*
C6	0.5719 (2)	0.16340 (15)	0.67218 (9)	0.0289 (3)
H6	0.6479	0.1849	0.7210	0.035*
C7	0.6958 (3)	0.10806 (19)	0.60294 (12)	0.0402 (4)
H7A	0.7301	0.0116	0.6156	0.048*
H7B	0.6280	0.1074	0.5509	0.048*
C8	0.8674 (3)	0.1948 (3)	0.59189 (15)	0.0547 (5)
H8A	0.8349	0.2879	0.5735	0.082*
H8B	0.9450	0.1510	0.5510	0.082*
H8C	0.9313	0.2009	0.6441	0.082*
N1	0.4361 (2)	0.05364 (15)	0.69611 (9)	0.0329 (3)
H1A	0.357 (3)	0.085 (2)	0.7347 (11)	0.048 (6)*
H1B	0.494 (3)	−0.0194 (17)	0.7180 (12)	0.043 (6)*
H1C	0.365 (2)	0.024 (2)	0.6543 (10)	0.036 (5)*
O7	0.36965 (18)	0.34047 (13)	0.72031 (9)	0.0399 (3)
H7	0.280 (2)	0.395 (2)	0.7049 (15)	0.056 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0552 (8)	0.0359 (6)	0.0380 (6)	0.0160 (6)	0.0062 (6)	−0.0002 (5)
O2	0.0458 (7)	0.0553 (8)	0.0268 (6)	0.0203 (7)	0.0003 (5)	−0.0058 (5)
O3	0.0395 (6)	0.0401 (6)	0.0290 (6)	0.0010 (6)	0.0035 (5)	0.0060 (5)
O4	0.0325 (7)	0.0368 (7)	0.0849 (11)	−0.0090 (6)	0.0227 (7)	−0.0090 (7)
O5	0.0271 (5)	0.0461 (7)	0.0302 (6)	−0.0025 (5)	0.0048 (4)	−0.0113 (5)
O6	0.0335 (6)	0.0518 (7)	0.0392 (6)	−0.0034 (6)	0.0015 (5)	−0.0175 (6)
C1	0.0280 (7)	0.0279 (6)	0.0295 (7)	−0.0026 (6)	0.0020 (6)	−0.0048 (6)
C2	0.0259 (7)	0.0266 (6)	0.0289 (7)	−0.0012 (6)	0.0052 (6)	−0.0010 (6)
C3	0.0275 (7)	0.0267 (6)	0.0310 (7)	−0.0008 (6)	0.0076 (6)	−0.0005 (6)
C4	0.0285 (7)	0.0277 (6)	0.0270 (7)	0.0006 (6)	0.0027 (6)	−0.0024 (6)
C5	0.0444 (9)	0.0287 (7)	0.0372 (8)	0.0062 (7)	0.0028 (7)	0.0023 (6)
C6	0.0321 (7)	0.0256 (7)	0.0290 (7)	−0.0004 (6)	0.0004 (6)	−0.0013 (6)
C7	0.0444 (9)	0.0351 (8)	0.0410 (9)	0.0022 (8)	0.0114 (8)	−0.0042 (7)
C8	0.0453 (11)	0.0643 (13)	0.0546 (12)	−0.0041 (11)	0.0165 (9)	−0.0001 (10)
N1	0.0377 (7)	0.0272 (6)	0.0338 (7)	−0.0009 (6)	0.0053 (6)	−0.0019 (5)
O7	0.0391 (6)	0.0347 (6)	0.0461 (7)	0.0089 (6)	0.0035 (6)	−0.0026 (5)

Geometric parameters (Å, º)

O1—C1	1.207 (2)	C5—H5A	0.9700
O2—C1	1.305 (2)	C5—H5B	0.9700
O2—H2	0.861 (10)	C6—N1	1.487 (2)
O3—C2	1.4015 (19)	C6—C7	1.524 (2)
O3—H3	0.853 (10)	C6—H6	0.9800
O4—C3	1.410 (2)	C7—C8	1.508 (3)
O4—H4	0.824 (10)	C7—H7A	0.9700
O5—C4	1.269 (2)	C7—H7B	0.9700
O6—C4	1.237 (2)	C8—H8A	0.9600
C1—C2	1.530 (2)	C8—H8B	0.9600
C2—C3	1.538 (2)	C8—H8C	0.9600
C2—H2A	0.9800	N1—H1A	0.893 (10)
C3—C4	1.528 (2)	N1—H1B	0.886 (10)
C3—H3A	0.9800	N1—H1C	0.890 (10)
C5—O7	1.419 (2)	O7—H7	0.866 (10)
C5—C6	1.514 (2)
C1—O2—H2	113 (2)	H5A—C5—H5B	108.5
C2—O3—H3	111.8 (17)	N1—C6—C5	107.67 (13)
C3—O4—H4	108 (2)	N1—C6—C7	109.98 (13)
O1—C1—O2	123.97 (14)	C5—C6—C7	113.68 (14)
O1—C1—C2	122.64 (14)	N1—C6—H6	108.5
O2—C1—C2	113.39 (13)	C5—C6—H6	108.5
O3—C2—C1	109.60 (12)	C7—C6—H6	108.5
O3—C2—C3	109.65 (13)	C8—C7—C6	112.93 (16)
C1—C2—C3	111.10 (13)	C8—C7—H7A	109.0
O3—C2—H2A	108.8	C6—C7—H7A	109.0
C1—C2—H2A	108.8	C8—C7—H7B	109.0
C3—C2—H2A	108.8	C6—C7—H7B	109.0
O4—C3—C4	110.03 (13)	H7A—C7—H7B	107.8
O4—C3—C2	111.40 (13)	C7—C8—H8A	109.5
C4—C3—C2	109.16 (13)	C7—C8—H8B	109.5
O4—C3—H3A	108.7	H8A—C8—H8B	109.5
C4—C3—H3A	108.7	C7—C8—H8C	109.5
C2—C3—H3A	108.7	H8A—C8—H8C	109.5
O6—C4—O5	124.29 (15)	H8B—C8—H8C	109.5
O6—C4—C3	119.60 (14)	C6—N1—H1A	112.1 (14)
O5—C4—C3	116.11 (14)	C6—N1—H1B	109.2 (15)
O7—C5—C6	107.40 (14)	H1A—N1—H1B	107 (2)
O7—C5—H5A	110.2	C6—N1—H1C	114.3 (13)
C6—C5—H5A	110.2	H1A—N1—H1C	104.6 (19)
O7—C5—H5B	110.2	H1B—N1—H1C	109 (2)
C6—C5—H5B	110.2	C5—O7—H7	108.9 (17)
O1—C1—C2—O3	−14.5 (2)	O4—C3—C4—O6	5.5 (2)
O2—C1—C2—O3	166.02 (13)	C2—C3—C4—O6	−117.06 (17)
O1—C1—C2—C3	−135.85 (16)	O4—C3—C4—O5	−173.70 (15)
O2—C1—C2—C3	44.69 (19)	C2—C3—C4—O5	63.76 (19)
O3—C2—C3—O4	−56.58 (17)	O7—C5—C6—N1	62.55 (17)
C1—C2—C3—O4	64.72 (18)	O7—C5—C6—C7	−175.36 (15)
O3—C2—C3—C4	65.13 (16)	N1—C6—C7—C8	−163.94 (16)
C1—C2—C3—C4	−173.56 (12)	C5—C6—C7—C8	75.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O4^i	0.87 (1)	2.44 (2)	3.0647 (19)	130 (2)
O7—H7···O6^i	0.87 (1)	1.89 (1)	2.7010 (18)	155 (2)
N1—H1C···O3^ii	0.89 (1)	2.36 (2)	2.8901 (19)	118 (2)
N1—H1C···O1^ii	0.89 (1)	2.00 (1)	2.860 (2)	163 (2)
N1—H1B···O7^ii	0.89 (1)	1.93 (1)	2.809 (2)	171 (2)
N1—H1A···O5^iii	0.89 (1)	2.04 (1)	2.8970 (18)	160 (2)
O4—H4···O2^iv	0.82 (1)	2.30 (2)	2.9879 (19)	142 (3)
O3—H3···O6^v	0.85 (1)	1.83 (1)	2.6777 (18)	172 (2)
O2—H2···O5^iv	0.86 (1)	1.65 (1)	2.5081 (17)	175 (3)

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