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From an aqueous solution of racemic 2,3-dibromo­succinic acid and (R)-1-phenyl­ethanamine, crystals of the title compound, C8H12N+·0.5C4H2Br2O42−·0.5C4H4Br2O4·H2O, were obtained in almost quanti­tative yield. The structure contains both enanti­omers of the starting material, dibromo­succinic acid. The S,S enanti­omer is present as a dianion and the R,R enanti­omer as the neutral acid; both of these components lie on twofold rotation axes. The structure features a complex two-dimensional network of hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007628/wn2006sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007628/wn2006Isup2.hkl
Contains datablock I

CCDC reference: 605204

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.059
  • wR factor = 0.120
  • Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 90 PerFit PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 90 PerFit
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 13 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br2 .. 3.59 Ang. PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.03
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 27.51 From the CIF: _reflns_number_total 3652 Count of symmetry unique reflns 2130 Completeness (_total/calc) 171.46% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1522 Fraction of Friedel pairs measured 0.715 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2003); data reduction: EVALCCD (Duisenberg, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: maXus (Mackay et al., 1999).

(R)-1-Phenylethanaminium–(S,S)-2,3-dibromosuccinate– (R,R)-2,3-dibromosuccinic acid–water (2/1/1/2) top
Crystal data top
C8H12N+·0.5C4H2Br2O42·0.5C4H4Br2O4·H2OF(000) = 824
Mr = 415.07Dx = 1.705 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 39 reflections
a = 12.609 (2) Åθ = 8.0–20.2°
b = 13.235 (3) ŵ = 5.03 mm1
c = 9.689 (2) ÅT = 299 K
V = 1616.8 (6) Å3Fragment, colourless
Z = 40.40 × 0.30 × 0.14 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
2529 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.075
φ and ω scansθmax = 27.5°, θmin = 4.5°
Absorption correction: numerical
(HABITUS; Herrendorf & Bärnighausen, 1997)
h = 1615
Tmin = 0.265, Tmax = 0.759k = 1617
12294 measured reflectionsl = 1112
3652 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.0061P)2 + 4.8215P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max < 0.001
S = 1.21Δρmax = 0.65 e Å3
3652 reflectionsΔρmin = 0.60 e Å3
181 parametersAbsolute structure: Flack (1983), 1550 Friedel pairs
0 restraintsAbsolute structure parameter: 0.00 (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
Br10.13275 (8)0.46912 (9)0.39939 (7)0.0718 (3)
O30.1973 (4)0.0311 (4)0.1058 (5)0.0488 (15)
H30.23910.00290.03380.059*
O40.0908 (4)0.1007 (4)0.0783 (6)0.0485 (14)
C30.1185 (6)0.0227 (5)0.1366 (6)0.0310 (15)
C40.0567 (5)0.0154 (6)0.2623 (6)0.0338 (16)
H40.06120.08930.26620.041*
O10.1979 (4)0.5360 (4)0.0837 (5)0.0462 (13)
C10.1186 (6)0.4810 (5)0.1150 (6)0.0316 (14)
O20.0919 (4)0.4059 (4)0.0548 (6)0.0461 (14)
C20.0560 (5)0.5188 (6)0.2401 (6)0.0319 (16)
H20.06880.59180.23580.038*
N10.2072 (4)0.2464 (5)0.9049 (5)0.0393 (12)
H1A0.27240.25100.89800.047*
H1B0.18160.31290.93840.047*
H1C0.18160.20880.96840.047*
C110.1695 (5)0.2197 (5)0.7626 (8)0.0377 (17)
H110.18410.14790.74750.045*
C100.0511 (5)0.2345 (6)0.7540 (7)0.0395 (17)
C90.0066 (9)0.3289 (7)0.7463 (11)0.066 (3)
H90.04950.38610.74820.079*
C50.0126 (8)0.1520 (7)0.7563 (11)0.064 (3)
H50.01730.08780.75980.077*
C80.1032 (10)0.3392 (10)0.7368 (12)0.084 (4)
H80.13330.40290.72720.100*
C60.1231 (10)0.1628 (10)0.7534 (12)0.088 (4)
H60.17460.10130.76170.105*
C70.1653 (7)0.2561 (13)0.7407 (11)0.088 (3)
H70.23850.26330.73420.106*
C120.2329 (6)0.2793 (7)0.6574 (9)0.057 (2)
H12A0.21810.25400.56660.069*
H12B0.30720.27210.67670.069*
H12C0.21360.34930.66240.069*
O50.0685 (3)0.7490 (5)0.0978 (5)0.0528 (12)
H5A0.02750.80260.09110.063*
H5B0.02780.70090.07120.063*
Br20.12994 (8)0.04180 (8)0.42145 (7)0.0578 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0415 (5)0.1352 (10)0.0386 (4)0.0213 (7)0.0113 (4)0.0044 (5)
O30.041 (3)0.050 (3)0.056 (3)0.023 (3)0.024 (2)0.020 (3)
O40.038 (3)0.049 (3)0.059 (3)0.014 (2)0.014 (3)0.020 (3)
C30.026 (4)0.038 (4)0.029 (3)0.005 (3)0.001 (3)0.007 (3)
C40.027 (3)0.043 (4)0.031 (3)0.006 (3)0.001 (3)0.002 (3)
O10.035 (3)0.046 (3)0.057 (3)0.006 (2)0.016 (2)0.015 (3)
C10.024 (3)0.038 (4)0.033 (3)0.005 (3)0.004 (3)0.007 (3)
O20.039 (3)0.044 (3)0.055 (3)0.010 (2)0.015 (3)0.015 (3)
C20.025 (3)0.044 (4)0.026 (3)0.000 (3)0.002 (2)0.003 (3)
N10.034 (2)0.045 (3)0.039 (3)0.002 (3)0.004 (2)0.002 (3)
C110.043 (4)0.026 (4)0.045 (4)0.003 (3)0.005 (3)0.003 (3)
C100.044 (4)0.038 (5)0.036 (4)0.000 (4)0.005 (3)0.001 (4)
C90.057 (6)0.055 (6)0.086 (7)0.000 (5)0.006 (6)0.015 (6)
C50.053 (6)0.052 (5)0.086 (7)0.015 (4)0.013 (5)0.003 (5)
C80.077 (9)0.093 (9)0.081 (7)0.029 (7)0.015 (7)0.016 (7)
C60.056 (7)0.107 (9)0.101 (8)0.041 (7)0.001 (7)0.014 (7)
C70.050 (5)0.129 (10)0.085 (7)0.017 (9)0.017 (5)0.009 (10)
C120.058 (5)0.068 (7)0.046 (5)0.008 (4)0.001 (4)0.012 (4)
O50.038 (2)0.040 (2)0.080 (4)0.004 (3)0.017 (2)0.004 (4)
Br20.0392 (4)0.0955 (7)0.0389 (4)0.0126 (5)0.0101 (3)0.0114 (4)
Geometric parameters (Å, º) top
C1—C21.530 (9)C11—C121.516 (10)
C1—O11.273 (9)C11—H110.9800
C1—O21.201 (8)C10—C51.356 (11)
C2—C2i1.497 (13)C10—C91.372 (12)
C2—H20.9817C9—C81.393 (15)
C2—Br11.936 (6)C9—H90.9300
C3—O31.258 (8)C5—C61.401 (17)
C3—O41.229 (8)C5—H50.9300
C3—C41.531 (8)C8—C71.351 (16)
O3—H30.9517C8—H80.9300
C4—C4ii1.487 (13)C6—C71.350 (16)
C4—Br21.950 (7)C6—H61.0437
C4—H40.9800C7—H70.9300
N1—C111.500 (8)C12—H12A0.9601
N1—H1A0.8265C12—H12B0.9600
N1—H1B0.9934C12—H12C0.9600
N1—H1C0.8541O5—H5A0.8801
C11—C101.508 (9)O5—H5B0.8569
C3—O3—H3112.9N1—C11—H11107.8
O4—C3—O3126.3 (6)C10—C11—H11107.7
O4—C3—C4119.9 (6)C12—C11—H11107.8
O3—C3—C4113.8 (6)C5—C10—C9119.5 (7)
C4ii—C4—C3113.5 (5)C5—C10—C11118.8 (8)
C4ii—C4—Br2110.4 (4)C9—C10—C11121.7 (8)
C3—C4—Br2105.1 (4)C10—C9—C8119.9 (10)
C4ii—C4—H4109.3C10—C9—H9120.1
C3—C4—H4109.3C8—C9—H9120.0
Br2—C4—H4109.3C10—C5—C6120.5 (10)
O2—C1—O1125.3 (7)C10—C5—H5119.8
O2—C1—C2120.7 (6)C6—C5—H5119.8
O1—C1—C2114.0 (6)C7—C8—C9119.7 (10)
C2i—C2—C1112.2 (5)C7—C8—H8120.3
C2i—C2—Br1111.0 (4)C9—C8—H8120.0
C1—C2—Br1105.2 (4)C7—C6—C5119.1 (10)
C2i—C2—H2118.8C7—C6—H6118.4
C1—C2—H2101.7C5—C6—H6122.5
Br1—C2—H2106.6C6—C7—C8121.2 (9)
C11—N1—H1A105.0C6—C7—H7119.4
C11—N1—H1B113.9C8—C7—H7119.3
H1A—N1—H1B106.5C11—C12—H12A109.4
C11—N1—H1C113.9C11—C12—H12B109.4
H1A—N1—H1C118.6H12A—C12—H12B109.5
H1B—N1—H1C99.1C11—C12—H12C109.6
N1—C11—C10109.5 (6)H12A—C12—H12C109.5
N1—C11—C12109.1 (6)H12B—C12—H12C109.5
C10—C11—C12114.7 (6)H5A—O5—H5B102.9
Symmetry codes: (i) x, y+1, z; (ii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1iii0.951.482.431 (6)177
N1—H1A···O5iv0.832.012.828 (6)172
N1—H1B···O2v0.992.022.947 (8)155
N1—H1C···O4v0.852.122.948 (8)164
O5—H5A···O4i0.881.972.833 (8)167
O5—H5B···O2i0.862.072.910 (8)165
Symmetry codes: (i) x, y+1, z; (iii) x+1/2, y1/2, z; (iv) x+1/2, y1/2, z+1; (v) x, y, z+1.
 

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