Monoclinic modification of N-benzyl-propan-2-aminium chloride.

In the title salt, C(10)H(16)N(+)·Cl(-), the cations and anions are linked by two N-H⋯Cl hydrogen bonds, forming a centrosymmetric tetramer.

Related literature

For the ortho­rhom­bic modification, see: Pourayoubi & Negari (2010 ▶).

Experimental

Crystal data

C10H16N+·Cl−

M = 185.69

Monoclinic,

a = 9.9566 (7) Å

b = 15.5072 (10) Å

c = 7.2179 (5) Å

β = 111.112 (1)°

V = 1039.63 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 120 K

0.26 × 0.26 × 0.11 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.922, T max = 0.966

15855 measured reflections

3008 independent reflections

2303 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.102

S = 1.00

3008 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001456X/ng2758sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001456X/ng2758Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H16N+·Cl−	F(000) = 400
Mr = 185.69	Dx = 1.186 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5439 reflections
a = 9.9566 (7) Å	θ = 2.2–29.9°
b = 15.5072 (10) Å	µ = 0.32 mm−1
c = 7.2179 (5) Å	T = 120 K
β = 111.112 (1)°	Prism, colorless
V = 1039.63 (12) Å3	0.26 × 0.26 × 0.11 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3008 independent reflections
Radiation source: fine-focus sealed tube	2303 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→14
Tmin = 0.922, Tmax = 0.966	k = −21→21
15855 measured reflections	l = −10→10

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)] = 0.048	Hydrogen site location: mixed
wR(F2) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.022P)2 + 1.240P] where P = (Fo2 + 2Fc2)/3
3008 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
Cl1	0.07253 (4)	0.60195 (3)	0.78749 (6)	0.02540 (11)
N1	−0.05680 (14)	0.41218 (8)	0.7852 (2)	0.0203 (3)
H1NA	−0.0578	0.4057	0.9086	0.024*
H1NB	−0.0137	0.4624	0.7773	0.024*
C1	0.2525 (2)	0.30399 (11)	1.0254 (3)	0.0290 (4)
H1A	0.1971	0.2680	1.0768	0.035*
C2	0.4001 (2)	0.31060 (13)	1.1261 (3)	0.0373 (4)
H2A	0.4450	0.2790	1.2453	0.045*
C3	0.4816 (2)	0.36310 (13)	1.0528 (3)	0.0393 (5)
H3A	0.5825	0.3680	1.1216	0.047*
C4	0.4152 (2)	0.40859 (12)	0.8782 (3)	0.0363 (4)
H4A	0.4709	0.4445	0.8270	0.044*
C5	0.2677 (2)	0.40188 (11)	0.7779 (3)	0.0280 (4)
H5A	0.2230	0.4334	0.6587	0.034*
C6	0.18499 (18)	0.34934 (10)	0.8506 (2)	0.0219 (3)
C7	0.02639 (18)	0.34037 (10)	0.7393 (3)	0.0243 (3)
H7A	0.0075	0.3398	0.5949	0.029*
H7B	−0.0069	0.2847	0.7744	0.029*
C8	−0.21251 (18)	0.41694 (11)	0.6481 (2)	0.0243 (3)
H8A	−0.2164	0.4219	0.5081	0.029*
C9	−0.2914 (2)	0.33546 (12)	0.6674 (3)	0.0340 (4)
H9A	−0.2479	0.2855	0.6276	0.051*
H9B	−0.3929	0.3399	0.5814	0.051*
H9C	−0.2841	0.3285	0.8056	0.051*
C10	−0.27797 (18)	0.49771 (12)	0.7003 (3)	0.0283 (4)
H10A	−0.2211	0.5481	0.6919	0.042*
H10B	−0.2779	0.4926	0.8357	0.042*
H10C	−0.3771	0.5045	0.6070	0.042*

	U11	U22	U33	U12	U13	U23
Cl1	0.0337 (2)	0.02088 (18)	0.0252 (2)	−0.00177 (15)	0.01491 (16)	0.00074 (15)
N1	0.0230 (6)	0.0190 (6)	0.0207 (6)	−0.0021 (5)	0.0101 (5)	−0.0017 (5)
C1	0.0358 (9)	0.0237 (8)	0.0296 (9)	0.0017 (7)	0.0144 (7)	0.0058 (7)
C2	0.0380 (10)	0.0320 (10)	0.0354 (10)	0.0086 (8)	0.0053 (8)	0.0012 (8)
C3	0.0274 (9)	0.0318 (10)	0.0553 (13)	0.0026 (7)	0.0109 (9)	−0.0149 (9)
C4	0.0374 (10)	0.0273 (9)	0.0550 (12)	−0.0049 (7)	0.0298 (9)	−0.0060 (8)
C5	0.0385 (9)	0.0208 (8)	0.0309 (9)	0.0011 (7)	0.0201 (8)	0.0013 (7)
C6	0.0293 (8)	0.0153 (7)	0.0245 (8)	0.0024 (6)	0.0139 (6)	−0.0011 (6)
C7	0.0305 (8)	0.0173 (7)	0.0264 (8)	0.0015 (6)	0.0120 (7)	−0.0031 (6)
C8	0.0237 (8)	0.0273 (8)	0.0213 (7)	−0.0013 (6)	0.0075 (6)	−0.0016 (6)
C9	0.0286 (9)	0.0344 (10)	0.0395 (10)	−0.0109 (7)	0.0130 (8)	−0.0092 (8)
C10	0.0236 (8)	0.0308 (9)	0.0308 (9)	0.0034 (6)	0.0102 (7)	0.0013 (7)

N1—C7	1.495 (2)	C5—H5A	0.9500
N1—C8	1.511 (2)	C6—C7	1.498 (2)
N1—H1NA	0.8999	C7—H7A	0.9900
N1—H1NB	0.9001	C7—H7B	0.9900
C1—C6	1.388 (2)	C8—C9	1.520 (2)
C1—C2	1.388 (3)	C8—C10	1.521 (2)
C1—H1A	0.9500	C8—H8A	1.0000
C2—C3	1.382 (3)	C9—H9A	0.9800
C2—H2A	0.9500	C9—H9B	0.9800
C3—C4	1.387 (3)	C9—H9C	0.9800
C3—H3A	0.9500	C10—H10A	0.9800
C4—C5	1.387 (3)	C10—H10B	0.9800
C4—H4A	0.9500	C10—H10C	0.9800
C5—C6	1.389 (2)
C7—N1—C8	114.28 (12)	N1—C7—C6	111.92 (13)
C7—N1—H1NA	110.0	N1—C7—H7A	109.2
C8—N1—H1NA	106.2	C6—C7—H7A	109.2
C7—N1—H1NB	108.4	N1—C7—H7B	109.2
C8—N1—H1NB	108.4	C6—C7—H7B	109.2
H1NA—N1—H1NB	109.5	H7A—C7—H7B	107.9
C6—C1—C2	120.88 (17)	N1—C8—C9	109.96 (14)
C6—C1—H1A	119.6	N1—C8—C10	107.96 (13)
C2—C1—H1A	119.6	C9—C8—C10	112.36 (14)
C3—C2—C1	119.97 (18)	N1—C8—H8A	108.8
C3—C2—H2A	120.0	C9—C8—H8A	108.8
C1—C2—H2A	120.0	C10—C8—H8A	108.8
C2—C3—C4	119.60 (18)	C8—C9—H9A	109.5
C2—C3—H3A	120.2	C8—C9—H9B	109.5
C4—C3—H3A	120.2	H9A—C9—H9B	109.5
C3—C4—C5	120.29 (18)	C8—C9—H9C	109.5
C3—C4—H4A	119.9	H9A—C9—H9C	109.5
C5—C4—H4A	119.9	H9B—C9—H9C	109.5
C4—C5—C6	120.49 (17)	C8—C10—H10A	109.5
C4—C5—H5A	119.8	C8—C10—H10B	109.5
C6—C5—H5A	119.8	H10A—C10—H10B	109.5
C1—C6—C5	118.77 (16)	C8—C10—H10C	109.5
C1—C6—C7	120.82 (15)	H10A—C10—H10C	109.5
C5—C6—C7	120.39 (15)	H10B—C10—H10C	109.5
C6—C1—C2—C3	0.2 (3)	C4—C5—C6—C7	−178.39 (15)
C1—C2—C3—C4	−0.3 (3)	C8—N1—C7—C6	168.23 (13)
C2—C3—C4—C5	0.3 (3)	C1—C6—C7—N1	97.96 (18)
C3—C4—C5—C6	−0.3 (3)	C5—C6—C7—N1	−83.50 (18)
C2—C1—C6—C5	−0.2 (3)	C7—N1—C8—C9	62.65 (17)
C2—C1—C6—C7	178.39 (16)	C7—N1—C8—C10	−174.45 (13)
C4—C5—C6—C1	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···Cl1i	0.90	2.25	3.1517 (14)	176
N1—H1NB···Cl1	0.90	2.32	3.2099 (14)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯Cl1i	0.90	2.25	3.1517 (14)	176
N1—H1NB⋯Cl1	0.90	2.32	3.2099 (14)	170

Symmetry code: (i) .