Monoclinic modification of N-benzyl­propan-2-aminium chloride

Pourayoubi, M.; Eshtiagh-Hosseini, H.; Negari, M.

doi:10.1107/S160053681001456X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1180

https://doi.org/10.1107/S160053681001456X

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Monoclinic modification of N-benzylpropan-2-aminium chloride

Mehrdad Pourayoubi,^a ^* Hossein Eshtiagh-Hosseini ^a and Monireh Negari ^a

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 11 April 2010; accepted 20 April 2010; online 28 April 2010)

In the title salt, C₁₀H₁₆N⁺·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_r = 185.69
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.102
S = 1.00
3008 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x, -y+1, -z+2.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001456X/ng2758Isup2.hkl

checkCIF report

Comment top

In the previous work, the structure determination of orthorhombic polymorph of N-benzylpropan-2-aminium chloride (Pourayoubi & Negari, 2010) has been investigated; we report here on the crystal structure of title compound (Fig. 1), a monoclinic polymorph of this salt. The cations and anions are linked together via two different N—H···Cl hydrogen bonds to form a centrosymmetric tetramer, in which two Cl^- anions act as a bridge between two C₁₀H₁₆N⁺ cations. The previously reported structure contains an extended zigzag chain arrangement of cations and anions via two different N—H···Cl hydrogen bonds.

Related literature top

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

Experimental top

The title compound is a by-product of the preparation of P(O)[OC₆H₅][N(CH₂C₆H₅)(CH(CH₃)₂)]Cl [from the reaction between P(O)[OC₆H₅]Cl₂ and NH(CH₂C₆H₅)(CH(CH₃)₂), with 1:2 mole ratio] in CCl₄.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A general view of the title salt, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level. N(1)—H(1NB)···Cl(1) bond is shown by dash line.

N-benzylpropan-2-aminium chloride top

Crystal data top

C₁₀H₁₆N⁺·Cl⁻	F(000) = 400
M_r = 185.69	D_x = 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

Data collection top

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

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)] = 0.048	Hydrogen site location: mixed
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.022P)² + 1.240P] where P = (F_o² + 2F_c²)/3
3008 reflections	(Δ/σ)_max < 0.001
111 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₀H₁₆N⁺·Cl⁻	V = 1039.63 (12) Å³
M_r = 185.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9566 (7) Å	µ = 0.32 mm⁻¹
b = 15.5072 (10) Å	T = 120 K
c = 7.2179 (5) Å	0.26 × 0.26 × 0.11 mm
β = 111.112 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3008 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2303 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.966	R_int = 0.032
15855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.67 e Å⁻³
3008 reflections	Δρ_min = −0.26 e Å⁻³
111 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N⁺·Cl⁻
M_r	185.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	9.9566 (7), 15.5072 (10), 7.2179 (5)
β (°)	111.112 (1)
V (Å³)	1039.63 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.26 × 0.26 × 0.11

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.922, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	15855, 3008, 2303
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.102, 1.00
No. of reflections	3008
No. of parameters	111
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.26

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+2.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Pourayoubi, M. & Negari, M. (2010). Acta Cryst. E66, o708. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar