The title compound, C
8H
11ClN
+·Cl
−, has been obtained as an intermediate in the synthesis of 2-phenylaziridine. There are two molecules in the asymmetric unit and these are linked in the crystal structure by a network of intermolecular N—H
Cl and C—H
Cl hydrogen bonds, plus an intermolecular Cl
Cl interaction.
Supporting information
CCDC reference: 279187
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.039
- wR factor = 0.098
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21A .. CL2 .. 2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H212 .. CL3 .. 3.13 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C8 H11 Cl N
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 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
3 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: OSCAIL (Version 9; McArdle, 2005) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1993); software used to prepare material for publication: OSCAIL (McArdle, 2005).
2-Chloro-2-phenylethylaminium chloride
top
Crystal data top
C8H11ClN+·Cl− | F(000) = 800 |
Mr = 192.08 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 8.4813 (13) Å | Cell parameters from 25 reflections |
b = 20.409 (5) Å | θ = 12–17° |
c = 10.939 (2) Å | µ = 0.62 mm−1 |
β = 90.719 (13)° | T = 298 K |
V = 1893.3 (6) Å3 | Block, colourless |
Z = 8 | 0.40 × 0.20 × 0.20 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1320 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al., 1968) | k = 0→24 |
Tmin = 0.789, Tmax = 0.886 | l = −12→12 |
3600 measured reflections | 2 standard reflections every 120 min |
3311 independent reflections | intensity decay: 1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 0.87 | w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3 |
3311 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | |
Cl1 | 0.49029 (13) | 0.41770 (5) | 0.91429 (10) | 0.0549 (3) | |
Cl2 | 0.00982 (14) | 0.09229 (5) | 0.97814 (9) | 0.0549 (3) | |
Cl3 | 0.14455 (13) | 0.55370 (5) | 0.85463 (9) | 0.0521 (3) | |
Cl4 | 0.35859 (13) | 0.00358 (6) | 0.83378 (9) | 0.0585 (3) | |
N11 | 0.2130 (4) | 0.45555 (16) | 1.0833 (3) | 0.0475 (9) | |
H11A | 0.2695 | 0.4718 | 1.1453 | 0.066* | |
H11B | 0.1108 | 0.4594 | 1.0993 | 0.066* | |
H11C | 0.2348 | 0.4775 | 1.0153 | 0.066* | |
N21 | 0.2817 (4) | 0.01341 (15) | 1.1169 (3) | 0.0459 (9) | |
H21A | 0.2315 | −0.0188 | 1.1552 | 0.064* | |
H21B | 0.3847 | 0.0104 | 1.1324 | 0.064* | |
H21C | 0.2642 | 0.0101 | 1.0368 | 0.064* | |
C23 | −0.0093 (4) | 0.14520 (19) | 1.2088 (3) | 0.0361 (10) | |
C13 | 0.4558 (5) | 0.3005 (2) | 1.0296 (4) | 0.0414 (10) | |
C22 | 0.0481 (4) | 0.08607 (19) | 1.1409 (3) | 0.0364 (10) | |
H22 | −0.0060 | 0.0472 | 1.1722 | 0.047* | |
C12 | 0.4246 (5) | 0.37335 (19) | 1.0457 (3) | 0.0429 (11) | |
H12 | 0.4844 | 0.3887 | 1.1173 | 0.056* | |
C21 | 0.2228 (4) | 0.07766 (19) | 1.1610 (3) | 0.0420 (10) | |
H211 | 0.2779 | 0.1125 | 1.1189 | 0.055* | |
H212 | 0.2467 | 0.0817 | 1.2476 | 0.055* | |
C28 | 0.0158 (5) | 0.2081 (2) | 1.1693 (4) | 0.0506 (11) | |
H28 | 0.0672 | 0.2156 | 1.0960 | 0.066* | |
C25 | −0.1332 (5) | 0.1872 (2) | 1.3875 (4) | 0.0570 (13) | |
H25 | −0.1807 | 0.1797 | 1.4623 | 0.074* | |
C14 | 0.3876 (6) | 0.2652 (2) | 0.9363 (4) | 0.0604 (13) | |
H14 | 0.3213 | 0.2860 | 0.8802 | 0.079* | |
C24 | −0.0851 (5) | 0.1355 (2) | 1.3181 (4) | 0.0499 (12) | |
H24 | −0.1039 | 0.0930 | 1.3450 | 0.065* | |
C18 | 0.5541 (5) | 0.2688 (2) | 1.1123 (4) | 0.0586 (13) | |
H18 | 0.5997 | 0.2921 | 1.1766 | 0.076* | |
C11 | 0.2527 (5) | 0.3859 (2) | 1.0666 (4) | 0.0490 (11) | |
H111 | 0.1927 | 0.3690 | 0.9974 | 0.064* | |
H112 | 0.2205 | 0.3618 | 1.1386 | 0.064* | |
C27 | −0.0362 (6) | 0.2609 (2) | 1.2394 (5) | 0.0647 (14) | |
H27 | −0.0198 | 0.3036 | 1.2128 | 0.084* | |
C26 | −0.1118 (5) | 0.2495 (2) | 1.3478 (5) | 0.0613 (14) | |
H26 | −0.1483 | 0.2845 | 1.3939 | 0.080* | |
C17 | 0.5848 (6) | 0.2029 (3) | 1.0998 (5) | 0.0720 (15) | |
H17 | 0.6517 | 0.1818 | 1.1552 | 0.094* | |
C16 | 0.5171 (7) | 0.1689 (3) | 1.0063 (6) | 0.0775 (16) | |
H16 | 0.5388 | 0.1245 | 0.9972 | 0.101* | |
C15 | 0.4168 (7) | 0.1994 (3) | 0.9253 (5) | 0.0746 (15) | |
H15 | 0.3687 | 0.1755 | 0.8628 | 0.097* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0523 (7) | 0.0599 (7) | 0.0527 (7) | −0.0020 (6) | 0.0021 (5) | 0.0084 (6) |
Cl2 | 0.0651 (8) | 0.0573 (7) | 0.0419 (6) | 0.0114 (7) | −0.0110 (6) | −0.0030 (5) |
Cl3 | 0.0542 (7) | 0.0560 (7) | 0.0463 (6) | 0.0079 (6) | 0.0047 (5) | −0.0025 (5) |
Cl4 | 0.0455 (7) | 0.0917 (9) | 0.0382 (6) | 0.0135 (7) | 0.0008 (5) | −0.0039 (6) |
N11 | 0.046 (2) | 0.056 (2) | 0.0401 (19) | 0.0080 (19) | 0.0022 (16) | −0.0003 (18) |
N21 | 0.036 (2) | 0.065 (3) | 0.0367 (19) | 0.0114 (19) | 0.0009 (15) | 0.0042 (17) |
C23 | 0.030 (2) | 0.034 (3) | 0.044 (2) | −0.003 (2) | −0.0003 (19) | 0.000 (2) |
C13 | 0.043 (3) | 0.045 (3) | 0.037 (2) | 0.005 (2) | 0.009 (2) | 0.001 (2) |
C22 | 0.035 (2) | 0.042 (3) | 0.032 (2) | 0.004 (2) | 0.0016 (18) | 0.008 (2) |
C12 | 0.045 (3) | 0.052 (3) | 0.032 (2) | 0.000 (2) | 0.0020 (19) | 0.000 (2) |
C21 | 0.042 (3) | 0.049 (3) | 0.034 (2) | 0.000 (2) | −0.0014 (19) | −0.003 (2) |
C28 | 0.055 (3) | 0.047 (3) | 0.050 (3) | −0.005 (3) | 0.011 (2) | 0.000 (2) |
C25 | 0.061 (3) | 0.059 (3) | 0.052 (3) | −0.005 (3) | 0.010 (2) | −0.008 (3) |
C14 | 0.084 (4) | 0.050 (3) | 0.048 (3) | 0.003 (3) | −0.007 (3) | 0.003 (2) |
C24 | 0.061 (3) | 0.037 (3) | 0.052 (3) | −0.003 (2) | 0.006 (2) | −0.001 (2) |
C18 | 0.049 (3) | 0.064 (4) | 0.063 (3) | 0.009 (3) | 0.005 (2) | 0.013 (3) |
C11 | 0.048 (3) | 0.050 (3) | 0.050 (3) | 0.000 (2) | 0.008 (2) | 0.001 (2) |
C27 | 0.075 (4) | 0.039 (3) | 0.080 (4) | −0.011 (3) | 0.007 (3) | −0.004 (3) |
C26 | 0.055 (3) | 0.054 (3) | 0.075 (4) | 0.003 (3) | 0.008 (3) | −0.030 (3) |
C17 | 0.053 (3) | 0.069 (4) | 0.094 (4) | 0.014 (3) | 0.008 (3) | 0.034 (3) |
C16 | 0.074 (4) | 0.053 (3) | 0.106 (5) | 0.004 (3) | 0.042 (4) | 0.012 (4) |
C15 | 0.094 (4) | 0.066 (4) | 0.064 (4) | −0.012 (4) | 0.017 (3) | −0.011 (3) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.793 (4) | C21—H212 | 0.9700 |
Cl2—C22 | 1.810 (4) | C28—C27 | 1.397 (6) |
N11—C11 | 1.472 (5) | C28—H28 | 0.9300 |
N11—H11A | 0.8900 | C25—C26 | 1.356 (6) |
N11—H11B | 0.8900 | C25—C24 | 1.365 (5) |
N11—H11C | 0.8900 | C25—H25 | 0.9300 |
N21—C21 | 1.486 (4) | C14—C15 | 1.371 (6) |
N21—H21A | 0.8900 | C14—H14 | 0.9300 |
N21—H21B | 0.8900 | C24—H24 | 0.9300 |
N21—H21C | 0.8900 | C18—C17 | 1.378 (6) |
C23—C28 | 1.373 (5) | C18—H18 | 0.9300 |
C23—C24 | 1.378 (5) | C11—H111 | 0.9700 |
C23—C22 | 1.502 (5) | C11—H112 | 0.9700 |
C13—C14 | 1.371 (6) | C27—C26 | 1.375 (6) |
C13—C18 | 1.382 (5) | C27—H27 | 0.9300 |
C13—C12 | 1.521 (5) | C26—H26 | 0.9300 |
C22—C21 | 1.505 (5) | C17—C16 | 1.357 (7) |
C22—H22 | 0.9800 | C17—H17 | 0.9300 |
C12—C11 | 1.501 (5) | C16—C15 | 1.370 (7) |
C12—H12 | 0.9800 | C16—H16 | 0.9300 |
C21—H211 | 0.9700 | C15—H15 | 0.9300 |
| | | |
C11—N11—H11A | 109.5 | C23—C28—C27 | 119.8 (4) |
C11—N11—H11B | 109.5 | C23—C28—H28 | 120.1 |
H11A—N11—H11B | 109.5 | C27—C28—H28 | 120.1 |
C11—N11—H11C | 109.5 | C26—C25—C24 | 120.3 (4) |
H11A—N11—H11C | 109.5 | C26—C25—H25 | 119.9 |
H11B—N11—H11C | 109.5 | C24—C25—H25 | 119.9 |
C21—N21—H21A | 109.5 | C13—C14—C15 | 120.3 (5) |
C21—N21—H21B | 109.5 | C13—C14—H14 | 119.9 |
H21A—N21—H21B | 109.5 | C15—C14—H14 | 119.9 |
C21—N21—H21C | 109.5 | C25—C24—C23 | 121.2 (4) |
H21A—N21—H21C | 109.5 | C25—C24—H24 | 119.4 |
H21B—N21—H21C | 109.5 | C23—C24—H24 | 119.4 |
C28—C23—C24 | 118.9 (4) | C17—C18—C13 | 120.3 (5) |
C28—C23—C22 | 122.9 (4) | C17—C18—H18 | 119.8 |
C24—C23—C22 | 118.2 (4) | C13—C18—H18 | 119.8 |
C14—C13—C18 | 119.1 (4) | N11—C11—C12 | 114.0 (3) |
C14—C13—C12 | 121.8 (4) | N11—C11—H111 | 108.7 |
C18—C13—C12 | 119.1 (4) | C12—C11—H111 | 108.7 |
C23—C22—C21 | 110.1 (3) | N11—C11—H112 | 108.7 |
C23—C22—Cl2 | 112.0 (3) | C12—C11—H112 | 108.7 |
C21—C22—Cl2 | 108.4 (2) | H111—C11—H112 | 107.6 |
C23—C22—H22 | 108.7 | C26—C27—C28 | 119.7 (4) |
C21—C22—H22 | 108.7 | C26—C27—H27 | 120.1 |
Cl2—C22—H22 | 108.7 | C28—C27—H27 | 120.1 |
C11—C12—C13 | 110.8 (3) | C25—C26—C27 | 120.1 (4) |
C11—C12—Cl1 | 110.4 (3) | C25—C26—H26 | 120.0 |
C13—C12—Cl1 | 110.2 (3) | C27—C26—H26 | 120.0 |
C11—C12—H12 | 108.5 | C16—C17—C18 | 119.7 (5) |
C13—C12—H12 | 108.5 | C16—C17—H17 | 120.2 |
Cl1—C12—H12 | 108.5 | C18—C17—H17 | 120.2 |
N21—C21—C22 | 112.8 (3) | C17—C16—C15 | 120.6 (5) |
N21—C21—H211 | 109.0 | C17—C16—H16 | 119.7 |
C22—C21—H211 | 109.0 | C15—C16—H16 | 119.7 |
N21—C21—H212 | 109.0 | C16—C15—C14 | 120.0 (5) |
C22—C21—H212 | 109.0 | C16—C15—H15 | 120.0 |
H211—C21—H212 | 107.8 | C14—C15—H15 | 120.0 |
| | | |
C28—C23—C22—C21 | 76.0 (4) | C26—C25—C24—C23 | 2.3 (7) |
C24—C23—C22—C21 | −101.4 (4) | C28—C23—C24—C25 | −0.9 (6) |
C28—C23—C22—Cl2 | −44.7 (5) | C22—C23—C24—C25 | 176.6 (4) |
C24—C23—C22—Cl2 | 137.8 (3) | C14—C13—C18—C17 | 1.0 (6) |
C14—C13—C12—C11 | 61.0 (5) | C12—C13—C18—C17 | −179.8 (4) |
C18—C13—C12—C11 | −118.2 (4) | C13—C12—C11—N11 | 179.9 (3) |
C14—C13—C12—Cl1 | −61.5 (5) | Cl1—C12—C11—N11 | −57.8 (4) |
C18—C13—C12—Cl1 | 119.3 (4) | C23—C28—C27—C26 | 0.2 (7) |
C23—C22—C21—N21 | 168.8 (3) | C24—C25—C26—C27 | −2.4 (7) |
Cl2—C22—C21—N21 | −68.3 (4) | C28—C27—C26—C25 | 1.2 (7) |
C24—C23—C28—C27 | −0.4 (6) | C13—C18—C17—C16 | −0.5 (7) |
C22—C23—C28—C27 | −177.8 (4) | C18—C17—C16—C15 | −0.8 (8) |
C18—C13—C14—C15 | 0.0 (7) | C17—C16—C15—C14 | 1.8 (8) |
C12—C13—C14—C15 | −179.2 (4) | C13—C14—C15—C16 | −1.3 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···Cl4i | 0.89 | 2.24 | 3.105 (3) | 163 |
N11—H11B···Cl3ii | 0.89 | 2.25 | 3.122 (3) | 168 |
N11—H11C···Cl3 | 0.89 | 2.46 | 3.251 (3) | 148 |
N21—H21A···Cl3i | 0.89 | 2.42 | 3.173 (3) | 143 |
N21—H21A···Cl2iii | 0.89 | 2.92 | 3.433 (3) | 119 |
N21—H21B···Cl4iv | 0.89 | 2.22 | 3.111 (3) | 176 |
N21—H21C···Cl4 | 0.89 | 2.37 | 3.180 (3) | 151 |
C21—H212···Cl1i | 0.97 | 2.74 | 3.560 (3) | 143 |
C21—H212···Cl3i | 0.97 | 3.13 | 3.485 (3) | 104 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y+1, −z+2; (iii) −x, −y, −z+2; (iv) −x+1, −y, −z+2. |