Phenyl­methanaminium chloro­acetate

Shahwar, D.; Tahir, M.N.; Ahmad, N.; Khan, M.A.; Yasmeen, A.

doi:10.1107/S1600536809017802

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1312

doi:10.1107/S1600536809017802

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Phenylmethanaminium chloroacetate

Durre Shahwar,^a M. Nawaz Tahir,^b ^* Naeem Ahmad,^a Muhammad Akmal Khan ^a and Asma Yasmeen ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 9 May 2009; accepted 12 May 2009; online 20 May 2009)

In the title compound, C₇H₁₀N⁺·C₂H₂ClO₂⁻, the planar chloracetate ion [with a maximum deviation of 0.025 (3) Å] is oriented at a dihedral angle of 31.07 (4)° with respect to the planar [maximum deviation of 0.022 (3) Å] phenylmethanaminium cation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into a network. A weak C—H⋯π interaction is also present.

Related literature

For related structures, see: Amini et al. (2007 ); Houllemare-Druot & Coquerel (1998 ); Rademeyer (2003 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₇H₁₀N⁺·C₂H₂ClO₂⁻
M_r = 201.65
Orthorhombic, P b c a
a = 11.1653 (9) Å
b = 8.0295 (5) Å
c = 22.3714 (18) Å
V = 2005.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.28 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.941, T_max = 0.958
11668 measured reflections
2485 independent reflections
1592 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.121
S = 1.03
2485 reflections
128 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.894 (16)	1.919 (17)	2.779 (2)	160.9 (16)
N1—H1B⋯O1ⁱⁱ	0.869 (19)	2.026 (19)	2.798 (2)	147.5 (17)
N1—H1C⋯O2ⁱⁱⁱ	0.94 (2)	1.80 (2)	2.740 (2)	175.5 (16)
C5—H5⋯Cg1^iv	0.93	2.93	3.777	152
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) x+1, y, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the benzene ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017802/hk2686sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017802/hk2686Isup2.hkl

checkCIF report

Comment top

Organic ammonium salts have many applications such as phase transfer catalysis, photo base-generators etc. We have prepared a scheme for synthesizing various ammonium salts, which will differ due to the moiety attached to NH₃ group and due to the anion. We reported herein the crystal structure of the title compound, (I), in this regard. The crystal structures of benzylammonium nitrate, (II) (Rademeyer, 2003), bis(benzylammonium) sulfate, (III) (Amini et al., 2007) and (±)-α-methylbenzylammonium chloroacetate, (IV) (Houllemare-Druot & Coquerel, 1998) have been reported.

The asymmetric unit of the title compound contains one cation and one anion (Fig. 1 ), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. The planar chloracetate ion [with a maximum deviation of 0.025 (3) Å for atom C8] is oriented with respect to the planar phenylmethane moiety [with a maximum deviation of -0.022 (3) Å for atom C7] at a dihedral angle of 31.07 (4)°, and atom N1 is 1.3132 (24) Å away from the plane of the phenylmethane moiety.

In the crystal structure, strong intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into a network (Fig. 2), in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For related structures, see: Amini et al. (2007); Houllemare-Druot & Coquerel (1998); Rademeyer (2003). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the benzene ring.

Experimental top

For the preparation of the title compound, benzylamine (1.09 ml, 0.01 mol) was added dropwise to a solution of chloroacetic acid (0.945 g, 0.01 mol) in dichloromethane (20 ml), and stirred for 30 min. The product precipitated, filtered out and washed with n-hexane. Crystals suitable for X-ray analysis were obtained from a mixture of n-hexane/chloroform (1:1).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Phenylmethanaminium chloroacetate top

Crystal data top

C₇H₁₀N⁺·C₂H₂ClO₂⁻	F(000) = 848
M_r = 201.65	D_x = 1.336 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2485 reflections
a = 11.1653 (9) Å	θ = 2.6–28.3°
b = 8.0295 (5) Å	µ = 0.35 mm⁻¹
c = 22.3714 (18) Å	T = 296 K
V = 2005.6 (3) Å³	Needle, colorless
Z = 8	0.28 × 0.14 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2485 independent reflections
Radiation source: fine-focus sealed tube	1592 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.6°
ω scans	h = −12→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→10
T_min = 0.941, T_max = 0.958	l = −29→29
11668 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0569P)² + 0.2834P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2485 reflections	Δρ_max = 0.21 e Å⁻³
128 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (11)

Crystal data top

C₇H₁₀N⁺·C₂H₂ClO₂⁻	V = 2005.6 (3) Å³
M_r = 201.65	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.1653 (9) Å	µ = 0.35 mm⁻¹
b = 8.0295 (5) Å	T = 296 K
c = 22.3714 (18) Å	0.28 × 0.14 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2485 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1592 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.958	R_int = 0.040
11668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
2485 reflections	Δρ_min = −0.20 e Å⁻³
128 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.22460 (4)	0.33171 (7)	0.07550 (3)	0.0665 (2)
O1	−0.01235 (10)	0.22583 (15)	0.03185 (6)	0.0435 (4)
O2	−0.11363 (11)	0.44211 (18)	0.06754 (7)	0.0586 (5)
N1	0.64467 (14)	0.4356 (2)	0.04653 (7)	0.0368 (5)
C1	0.59953 (15)	0.4607 (2)	0.15510 (8)	0.0376 (5)
C2	0.69962 (18)	0.4421 (3)	0.19030 (10)	0.0519 (7)
C3	0.7096 (2)	0.5291 (3)	0.24323 (11)	0.0684 (9)
C4	0.6222 (3)	0.6365 (3)	0.26080 (10)	0.0693 (9)
C5	0.5239 (2)	0.6594 (3)	0.22598 (11)	0.0634 (8)
C6	0.51145 (17)	0.5705 (2)	0.17352 (9)	0.0492 (6)
C7	0.58321 (18)	0.3615 (2)	0.09867 (9)	0.0495 (7)
C8	0.08928 (14)	0.4447 (2)	0.08390 (9)	0.0436 (6)
C9	−0.02110 (14)	0.3609 (2)	0.05846 (7)	0.0333 (5)
H1A	0.6185 (16)	0.540 (2)	0.0418 (8)	0.0442*
H1B	0.6233 (17)	0.376 (2)	0.0159 (9)	0.0442*
H1C	0.7280 (18)	0.436 (2)	0.0517 (8)	0.0442*
H2	0.76068	0.37060	0.17840	0.0623*
H3	0.77687	0.51420	0.26716	0.0821*
H4	0.62979	0.69415	0.29664	0.0832*
H5	0.46510	0.73487	0.23747	0.0761*
H6	0.44308	0.58455	0.15031	0.0590*
H7A	0.49832	0.35274	0.08999	0.0593*
H7B	0.61368	0.24974	0.10502	0.0593*
H8A	0.07616	0.46464	0.12616	0.0523*
H8B	0.09865	0.55221	0.06471	0.0523*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0303 (3)	0.0642 (4)	0.1049 (5)	0.0065 (2)	−0.0105 (3)	−0.0122 (3)
O1	0.0383 (7)	0.0417 (7)	0.0504 (7)	−0.0084 (5)	0.0054 (5)	−0.0141 (6)
O2	0.0301 (7)	0.0623 (10)	0.0834 (11)	0.0074 (6)	−0.0015 (6)	−0.0179 (8)
N1	0.0312 (7)	0.0368 (9)	0.0424 (9)	0.0039 (7)	−0.0020 (7)	−0.0106 (7)
C1	0.0378 (9)	0.0337 (9)	0.0412 (10)	−0.0065 (8)	0.0030 (8)	0.0045 (8)
C2	0.0450 (11)	0.0533 (13)	0.0573 (13)	0.0005 (9)	−0.0035 (9)	0.0111 (10)
C3	0.0693 (15)	0.0801 (17)	0.0558 (14)	−0.0243 (14)	−0.0217 (12)	0.0170 (13)
C4	0.105 (2)	0.0624 (16)	0.0404 (12)	−0.0273 (15)	0.0086 (13)	−0.0014 (10)
C5	0.0784 (16)	0.0544 (14)	0.0575 (13)	0.0027 (12)	0.0264 (13)	−0.0040 (11)
C6	0.0416 (10)	0.0540 (12)	0.0519 (11)	0.0062 (9)	0.0067 (9)	0.0063 (9)
C7	0.0511 (11)	0.0411 (11)	0.0562 (12)	−0.0094 (9)	0.0043 (10)	−0.0049 (9)
C8	0.0320 (8)	0.0410 (11)	0.0577 (11)	0.0024 (8)	−0.0047 (8)	−0.0138 (9)
C9	0.0293 (8)	0.0355 (10)	0.0350 (9)	−0.0021 (7)	0.0009 (7)	−0.0020 (8)

Geometric parameters (Å, º) top

Cl1—C8	1.7723 (17)	C4—C5	1.358 (4)
O1—C9	1.241 (2)	C5—C6	1.381 (3)
O2—C9	1.239 (2)	C2—H2	0.9300
N1—C7	1.478 (3)	C3—H3	0.9300
N1—H1A	0.894 (16)	C4—H4	0.9300
N1—H1B	0.869 (19)	C5—H5	0.9300
N1—H1C	0.94 (2)	C6—H6	0.9300
C1—C6	1.384 (2)	C7—H7A	0.9700
C1—C2	1.375 (3)	C7—H7B	0.9700
C1—C7	1.504 (3)	C8—C9	1.515 (2)
C2—C3	1.379 (3)	C8—H8A	0.9700
C3—C4	1.360 (4)	C8—H8B	0.9700

Cl1···O1	2.9455 (13)	C5···H3^xii	3.0000
Cl1···H7A	3.0800	C6···H3^xii	2.9700
Cl1···H1Bⁱ	2.871 (19)	C9···H1Cⁱⁱⁱ	2.87 (2)
Cl1···H8Bⁱⁱ	3.0000	C9···H1Bⁱ	2.998 (18)
O1···Cl1	2.9455 (13)	C9···H1Aⁱⁱ	2.822 (16)
O1···N1ⁱ	2.798 (2)	C9···H8B^ix	2.9700
O1···C7ⁱ	3.187 (2)	H1A···O1^iv	1.919 (17)
O1···C7ⁱⁱ	3.379 (2)	H1A···C9^iv	2.822 (16)
O1···N1ⁱⁱ	2.779 (2)	H1B···Cl1^vi	2.871 (19)
O1···C6ⁱⁱ	3.406 (2)	H1B···O1^vi	2.026 (19)
O2···N1ⁱⁱⁱ	2.740 (2)	H1B···C9^vi	2.998 (18)
O1···H7Aⁱ	2.8000	H1C···O2^v	1.80 (2)
O1···H1Aⁱⁱ	1.919 (17)	H1C···C9^v	2.87 (2)
O1···H1Bⁱ	2.026 (19)	H2···H7B	2.5200
O2···H1Cⁱⁱⁱ	1.80 (2)	H2···O2^v	2.9100
O2···H2ⁱⁱⁱ	2.9100	H2···C4^vii	2.9400
O2···H7B^iv	2.6100	H3···C6^xi	2.9700
N1···O1^iv	2.779 (2)	H3···C5^xi	3.0000
N1···O2^v	2.740 (2)	H4···H8A^xi	2.6000
N1···O1^vi	2.798 (2)	H5···C2^xiii	2.9600
C2···C4^vii	3.531 (4)	H5···C3^xiii	3.0900
C4···C2^viii	3.531 (4)	H5···C1^xiii	3.1000
C6···O1^iv	3.406 (2)	H6···H7A	2.3800
C6···C9^iv	3.475 (2)	H7A···Cl1	3.0800
C7···O1^iv	3.379 (2)	H7A···H6	2.3800
C7···O1^vi	3.187 (2)	H7A···O1^vi	2.8000
C9···C9^ix	3.472 (2)	H7B···H2	2.5200
C9···C6ⁱⁱ	3.475 (2)	H7B···O2ⁱⁱ	2.6100
C1···H5^x	3.1000	H8A···C4^xii	2.9300
C2···H5^x	2.9600	H8A···H4^xii	2.6000
C3···H5^x	3.0900	H8B···C9^ix	2.9700
C4···H2^viii	2.9400	H8B···Cl1^iv	3.0000
C4···H8A^xi	2.9300

H1B—N1—H1C	111.8 (16)	C5—C4—H4	120.00
C7—N1—H1C	111.4 (11)	C4—C5—H5	120.00
C7—N1—H1A	108.6 (12)	C6—C5—H5	120.00
C7—N1—H1B	105.8 (12)	C1—C6—H6	120.00
H1A—N1—H1B	109.5 (16)	C5—C6—H6	120.00
H1A—N1—H1C	109.6 (15)	N1—C7—H7A	109.00
C2—C1—C7	121.44 (17)	N1—C7—H7B	109.00
C2—C1—C6	118.44 (18)	C1—C7—H7A	109.00
C6—C1—C7	120.10 (16)	C1—C7—H7B	109.00
C1—C2—C3	120.2 (2)	H7A—C7—H7B	108.00
C2—C3—C4	120.7 (2)	Cl1—C8—C9	115.23 (12)
C3—C4—C5	120.0 (2)	O1—C9—O2	127.19 (15)
C4—C5—C6	119.9 (2)	O1—C9—C8	120.28 (14)
C1—C6—C5	120.74 (18)	O2—C9—C8	112.53 (14)
N1—C7—C1	113.14 (14)	Cl1—C8—H8A	108.00
C1—C2—H2	120.00	Cl1—C8—H8B	108.00
C3—C2—H2	120.00	C9—C8—H8A	108.00
C2—C3—H3	120.00	C9—C8—H8B	108.00
C4—C3—H3	120.00	H8A—C8—H8B	108.00
C3—C4—H4	120.00

C6—C1—C2—C3	1.3 (3)	C1—C2—C3—C4	−1.3 (4)
C7—C1—C2—C3	−177.00 (19)	C2—C3—C4—C5	−0.2 (4)
C2—C1—C6—C5	0.1 (3)	C3—C4—C5—C6	1.6 (4)
C7—C1—C6—C5	178.42 (18)	C4—C5—C6—C1	−1.6 (3)
C2—C1—C7—N1	−83.7 (2)	Cl1—C8—C9—O1	−2.8 (2)
C6—C1—C7—N1	98.1 (2)	Cl1—C8—C9—O2	177.43 (13)

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+1/2, y−1/2, z; (iii) x−1, y, z; (iv) −x+1/2, y+1/2, z; (v) x+1, y, z; (vi) x+1/2, −y+1/2, −z; (vii) −x+3/2, y−1/2, z; (viii) −x+3/2, y+1/2, z; (ix) −x, −y+1, −z; (x) −x+1, y−1/2, −z+1/2; (xi) x+1/2, y, −z+1/2; (xii) x−1/2, y, −z+1/2; (xiii) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^iv	0.894 (16)	1.919 (17)	2.779 (2)	160.9 (16)
N1—H1B···O1^vi	0.869 (19)	2.026 (19)	2.798 (2)	147.5 (17)
N1—H1C···O2^v	0.94 (2)	1.80 (2)	2.740 (2)	175.5 (16)
C5—H5···Cg1^xiii	0.93	2.93	3.777	152.00

Symmetry codes: (iv) −x+1/2, y+1/2, z; (v) x+1, y, z; (vi) x+1/2, −y+1/2, −z; (xiii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₇H₁₀N⁺·C₂H₂ClO₂⁻
M_r	201.65
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.1653 (9), 8.0295 (5), 22.3714 (18)
V (Å³)	2005.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.28 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.941, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	11668, 2485, 1592
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.03
No. of reflections	2485
No. of parameters	128
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.894 (16)	1.919 (17)	2.779 (2)	160.9 (16)
N1—H1B···O1ⁱⁱ	0.869 (19)	2.026 (19)	2.798 (2)	147.5 (17)
N1—H1C···O2ⁱⁱⁱ	0.94 (2)	1.80 (2)	2.740 (2)	175.5 (16)
C5—H5···Cg1^iv	0.93	2.93	3.777	152.00

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x+1/2, −y+1/2, −z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

NA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–120599-PS2–156).

References

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