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The title compound, C3H7NO2+.Br·C3H8NO2, crystallizes from an aqueous solution of D-alanine and racemic 2,3-dibromo­succinic acid. The structure includes alaninium cations and neutral zwitterionic alanine, and displays N—H...Br, N—H...O and O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048288/bi2106sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048288/bi2106Isup2.hkl
Contains datablock I

CCDC reference: 629449

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.054
  • wR factor = 0.134
  • Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.48 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
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 27.50 From the CIF: _reflns_number_total 2422 Count of symmetry unique reflns 1402 Completeness (_total/calc) 172.75% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1020 Fraction of Friedel pairs measured 0.728 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).

(I) top
Crystal data top
C3H7NO2+·Br·C3H8NO2F(000) = 264
Mr = 259.10Dx = 1.561 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 27 reflections
a = 9.485 (4) Åθ = 4.3–16.8°
b = 5.1678 (6) ŵ = 3.72 mm1
c = 11.258 (2) ÅT = 299 K
β = 92.97 (3)°Plate, colourless
V = 551.1 (3) Å30.31 × 0.19 × 0.06 mm
Z = 2
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2127 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.070
φ and ω scansθmax = 27.5°, θmin = 4.6°
Absorption correction: numerical
(HABITUS; Herrendorf & Bärnighausen, 1997)
h = 1112
Tmin = 0.378, Tmax = 0.774k = 66
6831 measured reflectionsl = 1413
2422 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0377P)2 + 1.5036P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134(Δ/σ)max < 0.001
S = 1.15Δρmax = 0.80 e Å3
2422 reflectionsΔρmin = 0.49 e Å3
123 parametersAbsolute structure: Flack (1983), 1033 Friedel pairs
1 restraintAbsolute structure parameter: 0.07 (3)
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
Br10.30824 (6)0.24804 (16)0.65061 (5)0.0475 (2)
C10.2961 (8)0.4423 (13)0.3014 (6)0.0426 (15)
C20.2671 (7)0.7095 (18)0.3559 (5)0.045 (2)
C30.1155 (8)0.737 (4)0.3899 (9)0.083 (3)
C40.7013 (8)0.4852 (14)0.0120 (6)0.0431 (15)
C50.7259 (6)0.248 (2)0.0634 (4)0.0407 (11)
C60.8735 (7)0.248 (3)0.1252 (8)0.074 (3)
N10.3645 (5)0.745 (2)0.4608 (4)0.0436 (10)
N20.6168 (5)0.240 (2)0.1526 (4)0.0432 (11)
O10.3885 (6)0.3025 (10)0.3425 (4)0.0549 (16)
O20.2118 (9)0.4015 (13)0.2112 (6)0.081 (2)
O30.7856 (7)0.5019 (11)0.0974 (5)0.0641 (16)
O40.6099 (6)0.6398 (10)0.0104 (4)0.0517 (12)
H1A0.34460.62960.51630.065*
H1B0.35490.90390.48950.065*
H1C0.45290.72200.44000.065*
H20.28670.84320.29730.054*
H2A0.63510.36140.20740.065*
H2B0.61730.08540.18700.065*
H2C0.53240.26940.11690.065*
H2D0.20970.24620.19620.122*
H3A0.08400.57650.42230.124*
H3B0.05700.78060.32060.124*
H3C0.10930.87130.44830.124*
H50.71580.09490.01260.049*
H6A0.89450.41680.15670.111*
H6B0.94180.20230.06880.111*
H6C0.87660.12380.18880.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0667 (4)0.0399 (3)0.0367 (3)0.0003 (5)0.0099 (2)0.0060 (4)
C10.066 (4)0.035 (3)0.027 (3)0.002 (3)0.007 (3)0.012 (3)
C20.065 (4)0.038 (6)0.030 (3)0.002 (3)0.001 (2)0.002 (3)
C30.058 (4)0.095 (7)0.095 (6)0.023 (8)0.008 (4)0.045 (9)
C40.057 (4)0.037 (3)0.035 (3)0.005 (3)0.006 (3)0.001 (3)
C50.055 (3)0.035 (2)0.032 (2)0.005 (6)0.005 (2)0.003 (5)
C60.050 (4)0.094 (6)0.077 (5)0.007 (8)0.000 (4)0.044 (8)
N10.054 (3)0.036 (2)0.042 (2)0.006 (5)0.0042 (19)0.005 (4)
N20.051 (2)0.045 (3)0.034 (2)0.006 (5)0.0014 (18)0.008 (4)
O10.067 (3)0.046 (5)0.051 (3)0.007 (2)0.000 (2)0.013 (2)
O20.127 (6)0.055 (4)0.060 (4)0.020 (4)0.025 (4)0.030 (3)
O30.097 (4)0.051 (3)0.046 (3)0.011 (3)0.022 (3)0.019 (2)
O40.063 (3)0.041 (2)0.050 (3)0.005 (2)0.004 (2)0.009 (2)
Geometric parameters (Å, º) top
N1—C21.472 (8)C5—H50.980
C5—N21.479 (6)N2—H2A0.890
C5—C41.500 (12)N2—H2B0.890
C5—C61.530 (9)N2—H2C0.890
O1—C11.209 (9)C6—H6A0.960
C2—C31.514 (10)C6—H6B0.960
C2—C11.541 (11)C6—H6C0.960
O3—C41.284 (9)C2—H20.980
O2—C11.277 (9)O2—H2D0.820
O4—C41.216 (9)C3—H3A0.960
N1—H1A0.890C3—H3B0.960
N1—H1B0.890C3—H3C0.960
N1—H1C0.890
N2—C5—C4108.3 (7)C5—N2—H2B109.5
N2—C5—C6110.3 (5)H2A—N2—H2B109.5
C4—C5—C6111.8 (9)C5—N2—H2C109.5
N1—C2—C3110.5 (6)H2A—N2—H2C109.5
N1—C2—C1108.2 (7)H2B—N2—H2C109.5
C3—C2—C1112.1 (8)C5—C6—H6A109.5
O4—C4—O3126.2 (7)C5—C6—H6B109.5
O4—C4—C5120.6 (6)H6A—C6—H6B109.5
O3—C4—C5113.2 (6)C5—C6—H6C109.5
O1—C1—O2128.1 (6)H6A—C6—H6C109.5
O1—C1—C2121.6 (6)H6B—C6—H6C109.5
O2—C1—C2110.3 (6)N1—C2—H2108.6
C2—N1—H1A109.5C3—C2—H2108.6
C2—N1—H1B109.5C1—C2—H2108.6
H1A—N1—H1B109.5C1—O2—H2D109.5
C2—N1—H1C109.5C2—C3—H3A109.5
H1A—N1—H1C109.5C2—C3—H3B109.5
H1B—N1—H1C109.5H3A—C3—H3B109.5
N2—C5—H5108.8C2—C3—H3C109.5
C4—C5—H5108.8H3A—C3—H3C109.5
C6—C5—H5108.8H3B—C3—H3C109.5
C5—N2—H2A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Br10.892.523.399 (9)170
N1—H1B···Br1i0.892.593.426 (9)156
N1—H1C···Br1ii0.892.543.408 (5)167
N2—H2A···Br1ii0.892.603.484 (9)174
N2—H2B···Br1iii0.892.603.424 (8)155
N2—H2C···O4iv0.892.032.802 (7)144
O2—H2D···O3iv0.821.692.431 (8)150
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+1; (iii) x+1, y1/2, z+1; (iv) x+1, y1/2, z.
 

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