2-Chloro-2-phenyl­ethyl­ammonium chloride

The title compound, C₈H₁₁ClN⁺·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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 8	0.40 × 0.20 × 0.20 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0401P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···Cl4^i	0.89	2.24	3.105 (3)	163
N11—H11B···Cl3^ii	0.89	2.25	3.122 (3)	168
N11—H11C···Cl3	0.89	2.46	3.251 (3)	148
N21—H21A···Cl3^i	0.89	2.42	3.173 (3)	143
N21—H21A···Cl2^iii	0.89	2.92	3.433 (3)	119
N21—H21B···Cl4^iv	0.89	2.22	3.111 (3)	176
N21—H21C···Cl4	0.89	2.37	3.180 (3)	151
C21—H212···Cl1^i	0.97	2.74	3.560 (3)	143
C21—H212···Cl3^i	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.