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2-Phenyl­ethyl­ammonium bromide, C8H12N+·Br, adopts a layered structure consisting of alternating hydro­philic and hydro­phobic regions. The ammonium groups and bromide anions inter­act through N+—H...Br hydrogen bonds, forming transoid one-dimensional ladders, which are further linked by electrostatic N+...Br inter­actions into two-dimensional sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051488/bi2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051488/bi2104Isup2.hkl
Contains datablock I

CCDC reference: 633610

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.032
  • wR factor = 0.059
  • Data-to-parameter ratio = 32.5

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 32.02 From the CIF: _reflns_number_total 2958 Count of symmetry unique reflns 1911 Completeness (_total/calc) 154.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1047 Fraction of Friedel pairs measured 0.548 Are heavy atom types Z>Si present yes
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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

2-Phenylethylammonium bromide top
Crystal data top
C8H12N+·BrF(000) = 408
Mr = 202.10Dx = 1.455 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4396 reflections
a = 4.6871 (4) Åθ = 3.8–32.0°
b = 6.1419 (4) ŵ = 4.39 mm1
c = 32.047 (2) ÅT = 295 K
V = 922.56 (12) Å3Block, colourless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Oxford Diffraction Excalibur2 CCD
diffractometer
2958 independent reflections
Radiation source: fine-focus sealed tube2063 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω–2θ scansθmax = 32.0°, θmin = 3.8°
Absorption correction: multi-scan
(Blessing, 1995)
h = 66
Tmin = 0.340, Tmax = 0.419k = 87
9448 measured reflectionsl = 4645
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0257P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.003
2958 reflectionsΔρmax = 0.46 e Å3
91 parametersΔρmin = 0.86 e Å3
0 restraintsAbsolute structure: Flack (1983), 1047 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.029 (15)
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
Br10.88110 (6)0.45078 (4)0.792497 (8)0.04480 (8)
N10.3964 (4)0.4462 (3)0.71525 (6)0.0421 (4)
H1A0.49920.43640.73850.063*
H1B0.28410.33000.71300.063*
H1C0.28970.56600.71620.063*
C10.5899 (5)0.4568 (4)0.67874 (7)0.0419 (5)
H1D0.70840.32740.67810.050*
H1E0.71430.58220.68150.050*
C20.4263 (5)0.4736 (5)0.63826 (8)0.0510 (7)
H2A0.31850.34080.63390.061*
H2B0.29200.59350.64000.061*
C30.6239 (6)0.5098 (4)0.60187 (8)0.0475 (6)
C40.7563 (7)0.7084 (6)0.59673 (10)0.0640 (9)
H40.72080.82070.61550.077*
C50.9434 (8)0.7414 (6)0.56346 (12)0.0784 (11)
H51.03390.87510.56020.094*
C60.9932 (8)0.5778 (8)0.53580 (12)0.0832 (12)
H61.11630.60080.51350.100*
C70.8653 (10)0.3822 (7)0.54052 (11)0.0827 (10)
H70.90100.27100.52150.099*
C80.6804 (7)0.3472 (6)0.57376 (11)0.0666 (9)
H80.59390.21200.57700.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04897 (14)0.03200 (11)0.05344 (14)0.00065 (13)0.00575 (15)0.00154 (12)
N10.0466 (11)0.0324 (9)0.0473 (11)0.0006 (14)0.0066 (11)0.0005 (9)
C10.0348 (13)0.0423 (11)0.0488 (13)0.0021 (15)0.0048 (12)0.0031 (12)
C20.0418 (16)0.0590 (16)0.0520 (15)0.0045 (14)0.0028 (12)0.0030 (13)
C30.0442 (13)0.0514 (18)0.0468 (14)0.0051 (15)0.0129 (14)0.0027 (10)
C40.073 (2)0.0584 (19)0.061 (2)0.0075 (16)0.0054 (17)0.0090 (16)
C50.074 (3)0.075 (2)0.086 (3)0.006 (2)0.010 (2)0.030 (2)
C60.074 (2)0.115 (3)0.061 (2)0.013 (2)0.0072 (17)0.022 (3)
C70.086 (3)0.102 (3)0.060 (2)0.015 (3)0.013 (2)0.0136 (18)
C80.062 (2)0.071 (2)0.067 (2)0.0030 (17)0.0009 (18)0.0100 (17)
Geometric parameters (Å, º) top
N1—C11.482 (3)C2—H2B0.970
N1—H1A0.890C8—C71.390 (5)
N1—H1B0.890C8—H80.930
N1—H1C0.890C5—C61.360 (5)
C1—C21.511 (3)C5—C41.396 (5)
C1—H1D0.970C5—H50.930
C1—H1E0.970C6—C71.351 (6)
C3—C81.370 (4)C6—H60.930
C3—C41.379 (4)C4—H40.930
C3—C21.506 (4)C7—H70.930
C2—H2A0.970
C1—N1—H1A109.5C3—C2—H2B109.4
C1—N1—H1B109.5C1—C2—H2B109.4
H1A—N1—H1B109.5H2A—C2—H2B108.0
C1—N1—H1C109.5C3—C8—C7120.8 (4)
H1A—N1—H1C109.5C3—C8—H8119.6
H1B—N1—H1C109.5C7—C8—H8119.6
N1—C1—C2111.73 (19)C6—C5—C4119.9 (4)
N1—C1—H1D109.3C6—C5—H5120.0
C2—C1—H1D109.3C4—C5—H5120.0
N1—C1—H1E109.3C7—C6—C5120.5 (4)
C2—C1—H1E109.3C7—C6—H6119.7
H1D—C1—H1E107.9C5—C6—H6119.7
C8—C3—C4118.6 (3)C3—C4—C5120.2 (3)
C8—C3—C2121.4 (3)C3—C4—H4119.9
C4—C3—C2120.0 (3)C5—C4—H4119.9
C3—C2—C1111.3 (2)C6—C7—C8120.0 (3)
C3—C2—H2A109.4C6—C7—H7120.0
C1—C2—H2A109.4C8—C7—H7120.0
C8—C3—C2—C1106.6 (3)C8—C3—C4—C50.0 (4)
C4—C3—C2—C172.2 (3)C2—C3—C4—C5178.9 (3)
N1—C1—C2—C3173.6 (2)C6—C5—C4—C30.6 (5)
C4—C3—C8—C70.6 (5)C5—C6—C7—C80.2 (6)
C2—C3—C8—C7179.4 (3)C3—C8—C7—C60.4 (6)
C4—C5—C6—C70.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Br10.892.493.360 (2)166
N1—H1B···Br1i0.892.463.3186 (19)162
N1—H1C···Br1ii0.892.513.370 (2)163
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1/2, z+3/2.
 

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