The title compound, C
8H
12N
+·Br
−, was obtained from an aqueous solution of (
R)-1-phenylethanamine and racemic 2,3-dibromosuccinic acid. It features a three-dimensional network of N—H
Br hydrogen bonds.
Supporting information
CCDC reference: 610907
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.008 Å
- R factor = 0.049
- wR factor = 0.081
- Data-to-parameter ratio = 22.8
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.116
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
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 2122
Count of symmetry unique reflns 1277
Completeness (_total/calc) 166.17%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 845
Fraction of Friedel pairs measured 0.662
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Collect (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).
(
R)-1-Phenylethanaminium bromide
top
Crystal data top
C8H12N+·Br− | Dx = 1.441 Mg m−3 |
Mr = 202.10 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 30 reflections |
Hall symbol: P 2ac 2ab | θ = 4.2–18.6° |
a = 5.5319 (9) Å | µ = 4.35 mm−1 |
b = 8.6962 (14) Å | T = 297 K |
c = 19.364 (4) Å | Needle, colourless |
V = 931.5 (3) Å3 | 0.16 × 0.04 × 0.03 mm |
Z = 4 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | Rint = 0.116 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 4.7° |
ω scans | h = −7→6 |
17585 measured reflections | k = −11→11 |
2122 independent reflections | l = −25→24 |
1500 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0116P)2 + 0.763P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.081 | (Δ/σ)max = 0.001 |
S = 1.16 | Δρmax = 0.49 e Å−3 |
2122 reflections | Δρmin = −0.35 e Å−3 |
93 parameters | Absolute structure: Flack (1983), 845 Friedel pairs |
0 restraints | Absolute structure parameter: 0.01 (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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.33190 (8) | 0.26030 (6) | 0.79002 (2) | 0.05407 (16) | |
N1 | 0.1801 (7) | 0.8878 (4) | 0.7860 (2) | 0.0528 (9) | |
C1 | 0.1933 (10) | 0.8236 (6) | 0.8570 (3) | 0.0542 (13) | |
C4 | 0.1408 (11) | 0.9291 (6) | 0.9750 (3) | 0.0617 (14) | |
C8 | −0.1474 (10) | 1.0020 (6) | 0.8915 (3) | 0.0551 (12) | |
C2 | 0.0991 (13) | 0.6601 (6) | 0.8559 (3) | 0.076 (2) | |
C3 | 0.0613 (9) | 0.9215 (5) | 0.9081 (3) | 0.0459 (12) | |
C6 | −0.1813 (12) | 1.0965 (6) | 1.0057 (3) | 0.0637 (14) | |
C7 | −0.2670 (10) | 1.0896 (6) | 0.9396 (3) | 0.0595 (14) | |
C5 | 0.0206 (12) | 1.0158 (7) | 1.0232 (3) | 0.0700 (16) | |
H1A | 0.0341 | 0.8701 | 0.7684 | 0.079* | |
H1B | 0.2916 | 0.8432 | 0.7596 | 0.079* | |
H1C | 0.2069 | 0.9887 | 0.7875 | 0.079* | |
H1 | 0.3638 | 0.8203 | 0.8707 | 0.065* | |
H4 | 0.2783 | 0.8747 | 0.9880 | 0.074* | |
H8 | −0.2077 | 0.9964 | 0.8468 | 0.066* | |
H2A | 0.1085 | 0.6172 | 0.9015 | 0.115* | |
H2B | 0.1951 | 0.5995 | 0.8248 | 0.115* | |
H2C | −0.0661 | 0.6599 | 0.8407 | 0.115* | |
H6 | −0.2605 | 1.1559 | 1.0386 | 0.076* | |
H7 | −0.4053 | 1.1439 | 0.9272 | 0.071* | |
H5 | 0.0776 | 1.0195 | 1.0683 | 0.084* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0504 (2) | 0.0475 (2) | 0.0643 (3) | −0.0041 (3) | 0.0017 (3) | 0.0041 (3) |
N1 | 0.047 (2) | 0.0481 (19) | 0.063 (2) | 0.000 (2) | 0.007 (3) | −0.007 (2) |
C1 | 0.041 (3) | 0.057 (3) | 0.064 (4) | 0.006 (3) | −0.004 (3) | −0.002 (2) |
C4 | 0.060 (3) | 0.068 (3) | 0.057 (3) | −0.001 (3) | −0.006 (3) | 0.001 (3) |
C8 | 0.050 (3) | 0.060 (3) | 0.055 (3) | −0.001 (3) | −0.001 (3) | −0.007 (2) |
C2 | 0.108 (6) | 0.049 (3) | 0.072 (4) | 0.014 (3) | −0.008 (4) | 0.005 (3) |
C3 | 0.039 (2) | 0.044 (3) | 0.055 (3) | −0.004 (2) | 0.000 (2) | −0.001 (2) |
C6 | 0.071 (4) | 0.058 (3) | 0.062 (4) | −0.004 (3) | 0.020 (4) | −0.011 (2) |
C7 | 0.059 (3) | 0.056 (3) | 0.064 (4) | 0.005 (2) | 0.010 (3) | 0.000 (3) |
C5 | 0.074 (4) | 0.084 (4) | 0.052 (3) | −0.013 (4) | −0.003 (3) | −0.001 (3) |
Geometric parameters (Å, º) top
N1—C1 | 1.486 (6) | N1—H1C | 0.8900 |
C1—C3 | 1.496 (7) | C1—H1 | 0.9800 |
C1—C2 | 1.515 (7) | C4—H4 | 0.9300 |
C4—C5 | 1.371 (8) | C8—H8 | 0.9300 |
C4—C3 | 1.371 (7) | C2—H2A | 0.9600 |
C8—C7 | 1.373 (7) | C2—H2B | 0.9600 |
C8—C3 | 1.387 (7) | C2—H2C | 0.9600 |
C6—C5 | 1.362 (9) | C6—H6 | 0.9300 |
C6—C7 | 1.367 (7) | C7—H7 | 0.9300 |
N1—H1A | 0.8900 | C5—H5 | 0.9300 |
N1—H1B | 0.8900 | | |
| | | |
N1—C1—C3 | 111.9 (4) | C3—C1—H1 | 107.9 |
N1—C1—C2 | 108.9 (5) | C2—C1—H1 | 107.9 |
C3—C1—C2 | 112.1 (5) | C5—C4—H4 | 119.5 |
C5—C4—C3 | 120.9 (5) | C3—C4—H4 | 119.5 |
C7—C8—C3 | 121.7 (5) | C7—C8—H8 | 119.2 |
C4—C3—C8 | 117.5 (5) | C3—C8—H8 | 119.2 |
C4—C3—C1 | 119.7 (5) | C1—C2—H2A | 109.5 |
C8—C3—C1 | 122.8 (5) | C1—C2—H2B | 109.5 |
C5—C6—C7 | 119.7 (5) | H2A—C2—H2B | 109.5 |
C6—C7—C8 | 119.5 (5) | C1—C2—H2C | 109.5 |
C6—C5—C4 | 120.8 (5) | H2A—C2—H2C | 109.5 |
C1—N1—H1A | 109.5 | H2B—C2—H2C | 109.5 |
C1—N1—H1B | 109.5 | C5—C6—H6 | 120.2 |
H1A—N1—H1B | 109.5 | C7—C6—H6 | 120.2 |
C1—N1—H1C | 109.5 | C6—C7—H7 | 120.3 |
H1A—N1—H1C | 109.5 | C8—C7—H7 | 120.3 |
H1B—N1—H1C | 109.5 | C6—C5—H5 | 119.6 |
N1—C1—H1 | 107.9 | C4—C5—H5 | 119.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Br1i | 0.89 | 2.51 | 3.379 (4) | 166 |
N1—H1B···Br1ii | 0.89 | 2.40 | 3.268 (4) | 164 |
N1—H1C···Br1iii | 0.89 | 2.46 | 3.347 (4) | 173 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x, y+1, z. |