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In the title compound, 2C5H11NO2·C4H6O4, the DL-valine mol­ecule exists in the zwitterionic form and the neutral succinic acid mol­ecule lies across an inversion center. There are no direct hydrogen-bonding interactions between succinic acid mol­ecules. Valine and succinic acid mol­ecules form alternating columns parallel to the c axis and are interlinked through characteristic hydrogen bonds to form a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011134/hg6046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011134/hg6046Isup2.hkl
Contains datablock I

CCDC reference: 242329

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.133
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.88
Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 28.01 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 1875 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2141 Completeness (_total/calc) 87.58% PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.04 Ratio
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 28.01 From the CIF: _reflns_number_total 1875 From the CIF: _diffrn_reflns_limit_ max hkl 30. 10. 10. From the CIF: _diffrn_reflns_limit_ min hkl -30. -9. -5. TEST1: Expected hkl limits for theta max Calculated maximum hkl 32. 10. 13. Calculated minimum hkl -32. -10. -13.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

DL-Valine–succinic acid (2/1) top
Crystal data top
2C5H11NO2·C4H6O4F(000) = 760
Mr = 352.38Dx = 1.316 Mg m3
Dm = 1.32 Mg m3
Dm measured by floatation in a mixture of xylene and bromoform
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1024 reflections
a = 24.373 (2) Åθ = 2.0–23.0°
b = 7.5744 (6) ŵ = 0.11 mm1
c = 10.0284 (9) ÅT = 293 K
β = 106.134 (2)°Block, colorless
V = 1778.4 (3) Å30.28 × 0.22 × 0.16 mm
Z = 4
Data collection top
CCD area-detector
diffractometer
1875 independent reflections
Radiation source: fine-focus sealed tube1620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 3030
Tmin = 0.96, Tmax = 0.99k = 910
5087 measured reflectionsl = 510
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0722P)2 + 1.2632P]
where P = (Fo2 + 2Fc2)/3
1875 reflections(Δ/σ)max < 0.001
113 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.20 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
O10.25764 (5)0.04824 (16)0.83991 (12)0.0347 (3)
O20.22223 (4)0.04981 (16)0.62358 (12)0.0349 (3)
O30.12444 (5)0.96157 (17)0.63389 (14)0.0402 (3)
H30.15441.00120.62420.060*
O40.08577 (5)1.13868 (19)0.45590 (14)0.0482 (4)
N10.31801 (5)0.19735 (16)0.60855 (13)0.0252 (3)
H1A0.30210.13570.53200.038*
H1B0.35290.23140.60800.038*
H1C0.29670.29200.61140.038*
C10.26185 (6)0.02329 (18)0.73212 (16)0.0239 (3)
C20.32178 (6)0.08532 (19)0.73262 (15)0.0232 (3)
H20.33640.15940.81500.028*
C30.36263 (7)0.0716 (2)0.74446 (18)0.0323 (4)
H3A0.36010.14010.82540.039*
C40.34551 (11)0.1940 (3)0.6215 (2)0.0604 (6)
H4A0.35030.13500.54070.091*
H4B0.30620.22750.60580.091*
H4C0.36910.29760.63960.091*
C50.42433 (9)0.0104 (4)0.7741 (4)0.0751 (9)
H5A0.44900.11140.78510.113*
H5B0.43430.05840.85780.113*
H5C0.42860.06030.69820.113*
C60.08163 (6)1.0302 (2)0.54106 (18)0.0314 (4)
C70.02524 (7)0.9582 (3)0.5489 (2)0.0518 (6)
H7A0.02430.83240.53030.062*
H7B0.02240.97380.64280.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (6)0.0438 (7)0.0313 (7)0.0069 (5)0.0108 (5)0.0097 (5)
O20.0198 (5)0.0498 (7)0.0339 (7)0.0044 (5)0.0055 (4)0.0091 (5)
O30.0213 (5)0.0481 (7)0.0503 (8)0.0028 (5)0.0085 (5)0.0135 (6)
O40.0249 (6)0.0611 (9)0.0579 (8)0.0054 (5)0.0103 (5)0.0244 (7)
N10.0191 (5)0.0276 (6)0.0303 (7)0.0007 (4)0.0091 (5)0.0041 (5)
C10.0223 (7)0.0234 (7)0.0277 (8)0.0016 (5)0.0099 (6)0.0001 (6)
C20.0204 (6)0.0274 (7)0.0218 (7)0.0014 (5)0.0058 (5)0.0008 (5)
C30.0278 (7)0.0347 (8)0.0359 (9)0.0079 (6)0.0116 (6)0.0102 (7)
C40.0863 (16)0.0470 (11)0.0491 (13)0.0283 (11)0.0211 (11)0.0015 (9)
C50.0275 (10)0.0699 (16)0.128 (3)0.0117 (10)0.0217 (12)0.0267 (15)
C60.0215 (7)0.0338 (8)0.0398 (10)0.0029 (6)0.0102 (6)0.0020 (7)
C70.0215 (8)0.0637 (13)0.0688 (14)0.0050 (8)0.0104 (8)0.0285 (11)
Geometric parameters (Å, º) top
O1—C11.2386 (19)C3—C51.522 (3)
O2—C11.2543 (18)C3—H3A0.9800
O3—C61.299 (2)C4—H4A0.9600
O3—H30.8200C4—H4B0.9600
O4—C61.209 (2)C4—H4C0.9600
N1—C21.4876 (18)C5—H5A0.9600
N1—H1A0.8900C5—H5B0.9600
N1—H1B0.8900C5—H5C0.9600
N1—H1C0.8900C6—C71.501 (2)
C1—C21.5331 (19)C7—C7i1.486 (4)
C2—C31.534 (2)C7—H7A0.9700
C2—H20.9800C7—H7B0.9700
C3—C41.506 (3)
C6—O3—H3109.5C3—C4—H4A109.5
C2—N1—H1A109.5C3—C4—H4B109.5
C2—N1—H1B109.5H4A—C4—H4B109.5
H1A—N1—H1B109.5C3—C4—H4C109.5
C2—N1—H1C109.5H4A—C4—H4C109.5
H1A—N1—H1C109.5H4B—C4—H4C109.5
H1B—N1—H1C109.5C3—C5—H5A109.5
O1—C1—O2126.64 (13)C3—C5—H5B109.5
O1—C1—C2116.18 (13)H5A—C5—H5B109.5
O2—C1—C2117.18 (13)C3—C5—H5C109.5
N1—C2—C1109.55 (11)H5A—C5—H5C109.5
N1—C2—C3113.25 (12)H5B—C5—H5C109.5
C1—C2—C3111.11 (12)O4—C6—O3124.78 (14)
N1—C2—H2107.6O4—C6—C7122.78 (15)
C1—C2—H2107.6O3—C6—C7112.43 (14)
C3—C2—H2107.6C7i—C7—C6114.36 (19)
C4—C3—C5112.42 (19)C7i—C7—H7A108.7
C4—C3—C2112.80 (14)C6—C7—H7A108.7
C5—C3—C2111.35 (15)C7i—C7—H7B108.7
C4—C3—H3A106.6C6—C7—H7B108.7
C5—C3—H3A106.6H7A—C7—H7B107.6
C2—C3—H3A106.6
O1—C1—C2—N1169.28 (13)C1—C2—C3—C463.94 (19)
O2—C1—C2—N110.68 (18)N1—C2—C3—C567.6 (2)
O1—C1—C2—C364.83 (17)C1—C2—C3—C5168.58 (17)
O2—C1—C2—C3115.20 (15)O4—C6—C7—C7i4.7 (4)
N1—C2—C3—C459.87 (19)O3—C6—C7—C7i176.0 (3)
Symmetry code: (i) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2ii0.821.702.5050 (15)169
N1—H1B···O4iii0.892.042.8814 (16)158
N1—H1C···O1iv0.891.952.8124 (16)162
N1—H1A···O1v0.892.042.9147 (17)167
Symmetry codes: (ii) x, y+1, z; (iii) x+1/2, y+3/2, z+1; (iv) x+1/2, y+1/2, z+3/2; (v) x, y, z1/2.
 

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