d-Phenyl-glycinium bromide.

In the crystal of the title salt, C8H10NO2 (+)·Br(-), the bromide anions and the phenylglycinium cations are -linked through N-H⋯Br, O-H⋯Br and C-H⋯O hydrogen bonds, generating sheets lying parallel to (001).

Related literature

For a similar compound with a different halogen anion, see: Ravichandran et al. (1998 ▶). For related structures and background, see: Srinivasan et al. (2001 ▶); Bouchouit et al. (2004 ▶); Ramaswamy et al. (2001 ▶); Bouacida et al. (2006 ▶); Thomsen et al. (1994 ▶). For biological importance, see: Satyam et al. (1996 ▶); Jayasinghe et al. (1994 ▶); Chun et al. (2010 ▶); Thomas & West (2011 ▶).

Experimental

Crystal data

C8H10NO2 +·Br−

M = 232.08

Orthorhombic,

a = 5.5240 (5) Å

b = 7.4735 (5) Å

c = 23.1229 (18) Å

V = 954.60 (13) Å3

Z = 4

Mo Kα radiation

μ = 4.27 mm−1

T = 295 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.317, T max = 0.415

5824 measured reflections

2170 independent reflections

2003 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.046

S = 1.03

2170 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: 0.011 (8)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004807/pk2465sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004807/pk2465Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004807/pk2465Isup3.cml

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

C8H10NO2+·Br−	F(000) = 464
Mr = 232.08	Dx = 1.615 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3239 reflections
a = 5.5240 (5) Å	θ = 2.6–28.8°
b = 7.4735 (5) Å	µ = 4.27 mm−1
c = 23.1229 (18) Å	T = 295 K
V = 954.60 (13) Å3	Block, colourless
Z = 4	0.35 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	2170 independent reflections
Radiation source: fine-focus sealed tube	2003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scan	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→7
Tmin = 0.317, Tmax = 0.415	k = −9→5
5824 measured reflections	l = −28→30

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.022	w = 1/[σ2(Fo2)]
wR(F2) = 0.046	(Δ/σ)max = 0.003
S = 1.03	Δρmax = 0.25 e Å−3
2170 reflections	Δρmin = −0.29 e Å−3
114 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0530 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Flack parameter: 0.011 (8)

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.

	x	y	z	Uiso*/Ueq
C1	0.1060 (5)	0.5444 (3)	0.56980 (9)	0.0370 (5)
H1	−0.0251	0.5884	0.5906	0.044*
C2	0.1209 (5)	0.5734 (3)	0.51081 (9)	0.0418 (6)
H2	−0.0006	0.6372	0.4921	0.050*
C3	0.3119 (5)	0.5092 (3)	0.47991 (9)	0.0424 (6)
H3	0.3196	0.5290	0.4402	0.051*
C4	0.4922 (5)	0.4160 (3)	0.50678 (9)	0.0443 (6)
H4	0.6229	0.3734	0.4855	0.053*
C5	0.4804 (4)	0.3849 (3)	0.56595 (9)	0.0355 (5)
H5	0.6024	0.3204	0.5842	0.043*
C6	0.2866 (4)	0.4500 (2)	0.59770 (7)	0.0264 (4)
C7	0.2695 (4)	0.4057 (2)	0.66152 (7)	0.0282 (5)
H7	0.4217	0.3499	0.6738	0.034*
C8	0.0650 (4)	0.2773 (3)	0.67328 (8)	0.0311 (5)
N1	0.2266 (4)	0.5687 (2)	0.69772 (6)	0.0345 (4)
H1A	0.3369	0.6514	0.6892	0.063 (8)*
H1B	0.2379	0.5399	0.7350	0.063 (8)*
H1C	0.0794	0.6117	0.6905	0.047 (7)*
O1	0.1199 (4)	0.1163 (2)	0.65347 (8)	0.0561 (5)
H1D	0.0051	0.0486	0.6586	0.084*
O2	−0.1206 (3)	0.3164 (2)	0.69632 (6)	0.0441 (4)
Br1	0.71415 (4)	0.82278 (3)	0.681529 (8)	0.03843 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0381 (14)	0.0388 (11)	0.0339 (11)	0.0062 (12)	0.0048 (10)	−0.0032 (10)
C2	0.0552 (17)	0.0342 (12)	0.0360 (12)	0.0066 (11)	−0.0030 (11)	0.0072 (10)
C3	0.0638 (18)	0.0364 (12)	0.0270 (10)	−0.0101 (13)	0.0087 (11)	0.0010 (9)
C4	0.0417 (16)	0.0496 (14)	0.0415 (14)	−0.0021 (12)	0.0170 (11)	−0.0082 (11)
C5	0.0277 (13)	0.0429 (12)	0.0360 (12)	0.0004 (11)	0.0035 (9)	−0.0027 (10)
C6	0.0261 (11)	0.0258 (9)	0.0273 (9)	−0.0062 (10)	0.0011 (9)	−0.0013 (7)
C7	0.0261 (13)	0.0316 (10)	0.0269 (9)	−0.0034 (10)	0.0012 (8)	0.0002 (7)
C8	0.0352 (14)	0.0323 (11)	0.0258 (11)	−0.0071 (10)	−0.0018 (9)	0.0014 (8)
N1	0.0377 (13)	0.0396 (9)	0.0262 (9)	−0.0137 (10)	0.0029 (8)	−0.0036 (7)
O1	0.0634 (15)	0.0333 (8)	0.0715 (12)	−0.0161 (9)	0.0238 (10)	−0.0057 (8)
O2	0.0328 (9)	0.0448 (9)	0.0547 (9)	−0.0106 (9)	0.0085 (7)	−0.0021 (8)
Br1	0.04061 (14)	0.03701 (12)	0.03766 (12)	−0.01269 (10)	0.00446 (10)	−0.00279 (9)

C1—C6	1.382 (3)	C6—C7	1.515 (2)
C1—C2	1.383 (3)	C7—N1	1.497 (2)
C1—H1	0.9300	C7—C8	1.507 (3)
C2—C3	1.361 (3)	C7—H7	0.9800
C2—H2	0.9300	C8—O2	1.192 (3)
C3—C4	1.365 (3)	C8—O1	1.323 (3)
C3—H3	0.9300	N1—H1A	0.8900
C4—C5	1.389 (3)	N1—H1B	0.8900
C4—H4	0.9300	N1—H1C	0.8900
C5—C6	1.386 (3)	O1—H1D	0.8200
C5—H5	0.9300
C6—C1—C2	119.8 (2)	C5—C6—C7	119.15 (19)
C6—C1—H1	120.1	N1—C7—C8	107.37 (17)
C2—C1—H1	120.1	N1—C7—C6	112.12 (15)
C3—C2—C1	120.6 (2)	C8—C7—C6	111.19 (16)
C3—C2—H2	119.7	N1—C7—H7	108.7
C1—C2—H2	119.7	C8—C7—H7	108.7
C2—C3—C4	120.4 (2)	C6—C7—H7	108.7
C2—C3—H3	119.8	O2—C8—O1	125.1 (2)
C4—C3—H3	119.8	O2—C8—C7	124.73 (19)
C3—C4—C5	120.0 (2)	O1—C8—C7	110.16 (19)
C3—C4—H4	120.0	C7—N1—H1A	109.5
C5—C4—H4	120.0	C7—N1—H1B	109.5
C6—C5—C4	119.9 (2)	H1A—N1—H1B	109.5
C6—C5—H5	120.0	C7—N1—H1C	109.5
C4—C5—H5	120.0	H1A—N1—H1C	109.5
C1—C6—C5	119.30 (19)	H1B—N1—H1C	109.5
C1—C6—C7	121.4 (2)	C8—O1—H1D	109.5
C6—C1—C2—C3	0.2 (4)	C1—C6—C7—N1	−54.0 (3)
C1—C2—C3—C4	−0.3 (4)	C5—C6—C7—N1	130.1 (2)
C2—C3—C4—C5	0.5 (4)	C1—C6—C7—C8	66.2 (2)
C3—C4—C5—C6	−0.6 (3)	C5—C6—C7—C8	−109.7 (2)
C2—C1—C6—C5	−0.2 (3)	N1—C7—C8—O2	15.6 (3)
C2—C1—C6—C7	−176.2 (2)	C6—C7—C8—O2	−107.4 (2)
C4—C5—C6—C1	0.5 (3)	N1—C7—C8—O1	−165.48 (17)
C4—C5—C6—C7	176.5 (2)	C6—C7—C8—O1	71.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Br1i	0.89	2.54	3.3586 (17)	154
N1—H1C···Br1ii	0.89	2.57	3.429 (2)	163
N1—H1A···Br1	0.89	2.45	3.3166 (18)	164
O1—H1D···Br1iii	0.82	2.39	3.2027 (17)	171
C7—H7···O2iv	0.98	2.59	3.527 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Br1i	0.89	2.54	3.3586 (17)	154
N1—H1C⋯Br1ii	0.89	2.57	3.429 (2)	163
N1—H1A⋯Br1	0.89	2.45	3.3166 (18)	164
O1—H1D⋯Br1iii	0.82	2.39	3.2027 (17)	171
C7—H7⋯O2iv	0.98	2.59	3.527 (3)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .