DL-Phenyl­glycinium chloride

In the title compound, C₈H₁₀NO₂⁺·Cl^-, the asymmetric unit consists of a protonated DL-phenyl­glycine cation and a chloride anion. The crystal structure consists of alternating layers of hydro­phobic and hydro­philic zones of phenyl­glycinium along the c axis. The chloride anions are located between hydro­phobic zones, forming hydrogen bonds with N and O atoms of the cations, in hydro­philic zones. These ions are linked by cation-cation and cation-anion hydrogen bonds. This three-dimensional complex network of hydrogen bonds reinforces the cohesion of the ionic structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.116
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(I)

Crystal data

C8H10NO2^+·Cl^−	F(000) = 784
Mr = 187.62	Dx = 1.446 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 20517 reflections
a = 7.303 (2) Å	θ = 1.9–27.6°
b = 11.005 (2) Å	µ = 0.4 mm^−1
c = 21.447 (4) Å	T = 296 K
V = 1723.7 (7) Å^3	Prism, colourless
Z = 8	0.13 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	1563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.6°, θmin = 1.9°
φ scans, and ω scans with κ offsets	h = −9→9
20517 measured reflections	k = −14→11
1979 independent reflections	l = −27→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 1.3984P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
1979 reflections	Δρmax = 0.32 e Å^−3
109 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

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	−0.24540 (5)	0.62877 (3)	0.926359 (19)	0.03243 (17)
O1	0.22347 (16)	0.55882 (10)	0.94637 (6)	0.0314 (3)
O2	0.45649 (18)	0.43732 (13)	0.91952 (6)	0.0430 (4)
H2	0.5190	0.4967	0.9286	0.065*
N1	−0.0165 (2)	0.36896 (12)	0.94555 (7)	0.0308 (3)
H1A	0.0022	0.3742	0.9865	0.046*
H1B	−0.0873	0.3051	0.9374	0.046*
H1C	−0.0713	0.4363	0.9321	0.046*
C2	0.1391 (2)	0.34440 (14)	0.84314 (7)	0.0233 (3)
C1	0.1623 (2)	0.35436 (14)	0.91314 (7)	0.0244 (3)
H1	0.2212	0.2800	0.9284	0.029*
C3	0.0697 (2)	0.44071 (14)	0.80843 (7)	0.0281 (4)
H3	0.0293	0.5108	0.8283	0.034*
C7	0.1954 (2)	0.23959 (14)	0.81299 (8)	0.0290 (4)
H7	0.2397	0.1744	0.8361	0.035*
C5	0.1203 (2)	0.32736 (17)	0.71439 (7)	0.0327 (4)
H5	0.1159	0.3221	0.6711	0.039*
C4	0.0609 (2)	0.43167 (16)	0.74397 (8)	0.0332 (4)
H4	0.0150	0.4960	0.7206	0.040*
C8	0.2836 (2)	0.46209 (15)	0.92932 (7)	0.0252 (3)
C6	0.1861 (2)	0.23127 (16)	0.74877 (8)	0.0334 (4)
H6	0.2243	0.1607	0.7288	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0310 (3)	0.0298 (3)	0.0365 (3)	0.00346 (15)	−0.00030 (16)	0.00309 (15)
O1	0.0343 (7)	0.0231 (6)	0.0367 (6)	−0.0017 (5)	0.0043 (5)	−0.0026 (5)
O2	0.0275 (7)	0.0431 (8)	0.0585 (8)	−0.0034 (6)	0.0040 (6)	−0.0187 (6)
N1	0.0324 (8)	0.0284 (7)	0.0316 (7)	−0.0073 (6)	0.0072 (6)	−0.0041 (5)
C2	0.0227 (7)	0.0230 (7)	0.0242 (7)	−0.0043 (6)	0.0009 (6)	−0.0013 (6)
C1	0.0267 (8)	0.0217 (8)	0.0249 (7)	−0.0003 (6)	0.0015 (6)	−0.0001 (6)
C3	0.0296 (8)	0.0242 (8)	0.0306 (8)	0.0006 (6)	−0.0021 (6)	−0.0015 (6)
C7	0.0340 (9)	0.0224 (8)	0.0306 (8)	0.0012 (6)	0.0008 (7)	0.0002 (6)
C5	0.0307 (8)	0.0429 (10)	0.0244 (8)	−0.0059 (8)	−0.0022 (6)	−0.0023 (7)
C4	0.0321 (8)	0.0345 (9)	0.0330 (9)	−0.0016 (7)	−0.0073 (7)	0.0061 (7)
C8	0.0264 (8)	0.0287 (9)	0.0206 (7)	−0.0020 (6)	0.0011 (6)	−0.0004 (6)
C6	0.0351 (9)	0.0320 (9)	0.0331 (8)	0.0000 (7)	0.0025 (7)	−0.0098 (7)

Geometric parameters (Å, º)

O1—C8	1.208 (2)	C1—H1	0.9800
O2—C8	1.308 (2)	C3—C4	1.388 (2)
O2—H2	0.8200	C3—H3	0.9300
N1—C1	1.488 (2)	C7—C6	1.382 (2)
N1—H1A	0.8900	C7—H7	0.9300
N1—H1B	0.8900	C5—C6	1.376 (3)
N1—H1C	0.8900	C5—C4	1.381 (3)
C2—C7	1.385 (2)	C5—H5	0.9300
C2—C3	1.391 (2)	C4—H4	0.9300
C2—C1	1.515 (2)	C6—H6	0.9300
C1—C8	1.520 (2)
C8—O2—H2	109.5	C4—C3—H3	120.2
C1—N1—H1A	109.5	C2—C3—H3	120.2
C1—N1—H1B	109.5	C6—C7—C2	120.39 (15)
H1A—N1—H1B	109.5	C6—C7—H7	119.8
C1—N1—H1C	109.5	C2—C7—H7	119.8
H1A—N1—H1C	109.5	C6—C5—C4	120.15 (15)
H1B—N1—H1C	109.5	C6—C5—H5	119.9
C7—C2—C3	119.55 (14)	C4—C5—H5	119.9
C7—C2—C1	119.33 (14)	C5—C4—C3	120.18 (15)
C3—C2—C1	121.06 (14)	C5—C4—H4	119.9
N1—C1—C2	111.88 (13)	C3—C4—H4	119.9
N1—C1—C8	108.69 (12)	O1—C8—O2	125.66 (15)
C2—C1—C8	110.37 (12)	O1—C8—C1	122.97 (15)
N1—C1—H1	108.6	O2—C8—C1	111.29 (13)
C2—C1—H1	108.6	C5—C6—C7	120.02 (16)
C8—C1—H1	108.6	C5—C6—H6	120.0
C4—C3—C2	119.69 (15)	C7—C6—H6	120.0
C7—C2—C1—N1	−118.51 (16)	C6—C5—C4—C3	0.9 (3)
C3—C2—C1—N1	64.33 (18)	C2—C3—C4—C5	0.2 (2)
C7—C2—C1—C8	120.33 (16)	N1—C1—C8—O1	−23.3 (2)
C3—C2—C1—C8	−56.84 (19)	C2—C1—C8—O1	99.77 (17)
C7—C2—C3—C4	−1.3 (2)	N1—C1—C8—O2	159.70 (13)
C1—C2—C3—C4	175.90 (15)	C2—C1—C8—O2	−77.26 (17)
C3—C2—C7—C6	1.2 (2)	C4—C5—C6—C7	−1.0 (3)
C1—C2—C7—C6	−175.99 (15)	C2—C7—C6—C5	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^i	0.89	2.58	3.3475 (18)	145
N1—H1A···O1^i	0.89	2.31	2.879 (2)	122
N1—H1B···Cl1^ii	0.89	2.31	3.1906 (17)	173
N1—H1C···Cl1	0.89	2.47	3.3375 (17)	164
O2—H2···Cl1^iii	0.82	2.25	3.0332 (16)	159
C1—H1···O1^iv	0.98	2.50	3.433 (2)	159
C5—H5···O2^v	0.93	2.60	3.338 (2)	137

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x−1/2, y−1/2, z; (iii) x+1, y, z; (iv) −x+1/2, y−1/2, z; (v) x−1/2, y, −z+3/2.