d-Phenyl­glycinium perchlorate

Ramaswamy, S.; Sridhar, B.; Ramakrishnan, V.; Rajaram, R.K.

doi:10.1107/S160053680101858X

D-Phenylglycinium perchlorate

S. Ramaswamy, B. Sridhar, V. Ramakrishnan and R. K. Rajaram

In the title compound, C₈H₁₀NO₂⁺·ClO₄⁻, the phenylglycinium cation is linked to the perchlorate anion through a normal O—H

O [2.78 (2) Å] hydrogen bond. The phenylglycinium cation and perchlorate anion are also held together by N—H

O hydrogen bonds. Chelated three-centered hydrogen bonds are observed involving the amino-N atom and the perchlorate-O atoms. The molecular aggregation of the hydrophilic zone at z = $1 \over 4$ is sandwiched between two hydrophobic zones.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101858X/wn6065sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680101858X/wn6065Isup2.hkl Contains datablock I

CCDC reference: 177197

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
Disorder in solvent or counterion
R factor = 0.056
wR factor = 0.161
Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack   -0.980
         From the CIF: _refine_ls_abs_structure_Flack_su    0.160
           Alert C Flack parameter is too small

PLAT_302  Alert C Anion/Solvent Disorder .......................      44.00 Perc.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.28
         From the CIF: _reflns_number_total               1261
         Count of symmetry unique reflns         1188
         Completeness (_total/calc)            106.14%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured        73
         Fraction of Friedel pairs measured     0.061
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

D-phenylglycinium perchlorate top

Crystal data top

C₈H₁₀NO₂⁺.ClO₄⁻	D_x = 1.537 Mg m⁻³ D_m = 1.530 Mg m⁻³ D_m measured by flotation technique using a mixture of carbon tetrachloride and xylene
M_r = 251.62	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 25 reflections
a = 5.451 (1) Å	θ = 13.6–23.0°
b = 8.807 (2) Å	µ = 0.37 mm⁻¹
c = 22.649 (5) Å	T = 293 K
V = 1087.3 (4) Å³	Needle, colorless
Z = 4	0.55 × 0.50 × 0.15 mm
F(000) = 520

Data collection top

Enraf-Nonis sealed tube diffractometer	1193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω–2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
T_min = 0.864, T_max = 0.947	l = 0→27
1485 measured reflections	3 standard reflections every 60 min
1261 independent reflections	intensity decay: none

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.1125P)² + 0.6721P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1261 reflections	Δρ_max = 0.33 e Å⁻³
181 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.98 (16)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.0200 (2)	0.18151 (14)	0.31252 (5)	0.0558 (4)
O1	0.079 (3)	0.328 (3)	0.3277 (8)	0.101 (6)	0.50
O2	−0.027 (4)	0.143 (4)	0.2544 (10)	0.146 (11)	0.50
O3	−0.149 (6)	0.135 (2)	0.3507 (10)	0.139 (12)	0.50
O4	0.187 (5)	0.078 (3)	0.3430 (15)	0.227 (14)	0.50
O1'	−0.016 (3)	0.340 (2)	0.3052 (8)	0.092 (4)	0.50
O2'	0.017 (4)	0.119 (3)	0.2570 (12)	0.132 (9)	0.50
O3'	−0.200 (5)	0.132 (2)	0.3420 (11)	0.120 (8)	0.50
O4'	0.269 (3)	0.156 (2)	0.3260 (6)	0.134 (7)	0.50
O1A	0.5190 (9)	0.8079 (4)	0.29331 (15)	0.0712 (11)
O1B	0.7712 (8)	0.8274 (4)	0.36966 (14)	0.0682 (11)
H12	0.7769	0.9174	0.3606	0.102*
C11	0.6297 (9)	0.7563 (5)	0.33355 (16)	0.0453 (11)
C12	0.6124 (9)	0.5885 (5)	0.34892 (16)	0.0449 (11)
H12A	0.7788	0.5494	0.3550	0.054*
N11	0.5040 (9)	0.5103 (5)	0.29656 (14)	0.0588 (11)
H11A	0.5953	0.5294	0.2648	0.088*
H11B	0.3523	0.5443	0.2906	0.088*
H11C	0.5000	0.4107	0.3030	0.088*
C13	0.4637 (9)	0.5580 (5)	0.40412 (16)	0.0450 (11)
C14	0.2607 (9)	0.6449 (6)	0.41674 (19)	0.0540 (12)
H14	0.2174	0.7246	0.3919	0.065*
C15	0.1211 (12)	0.6143 (8)	0.4662 (2)	0.0700 (16)
H15	−0.0167	0.6727	0.4746	0.084*
C16	0.1871 (14)	0.4966 (8)	0.5031 (2)	0.081 (2)
H16	0.0939	0.4761	0.5366	0.097*
C17	0.3888 (18)	0.4099 (9)	0.4908 (2)	0.091 (2)
H17	0.4322	0.3302	0.5156	0.109*
C18	0.5280 (13)	0.4417 (6)	0.4411 (2)	0.0666 (15)
H18	0.6662	0.3835	0.4328	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0486 (6)	0.0514 (8)	0.0674 (7)	−0.0024 (6)	0.0163 (6)	−0.0056 (5)
O1	0.084 (10)	0.083 (11)	0.136 (13)	−0.035 (10)	0.029 (9)	−0.026 (10)
O2	0.086 (10)	0.26 (3)	0.088 (11)	−0.080 (14)	−0.007 (8)	−0.053 (13)
O3	0.18 (3)	0.088 (12)	0.152 (14)	−0.041 (12)	0.108 (15)	−0.075 (11)
O4	0.14 (2)	0.159 (17)	0.38 (4)	0.049 (14)	−0.04 (2)	0.11 (2)
O1'	0.087 (10)	0.048 (5)	0.140 (13)	0.007 (9)	0.000 (8)	−0.006 (8)
O2'	0.122 (14)	0.131 (12)	0.143 (17)	0.023 (10)	0.079 (11)	−0.074 (11)
O3'	0.096 (10)	0.083 (11)	0.182 (17)	−0.016 (8)	0.073 (11)	0.057 (11)
O4'	0.079 (8)	0.23 (2)	0.096 (7)	0.061 (12)	0.003 (6)	0.067 (10)
O1A	0.088 (3)	0.071 (2)	0.0542 (17)	−0.003 (3)	−0.009 (2)	0.0152 (16)
O1B	0.089 (3)	0.060 (2)	0.0556 (18)	−0.024 (2)	−0.0085 (19)	0.0006 (16)
C11	0.054 (3)	0.053 (2)	0.0292 (16)	−0.007 (2)	0.0099 (19)	0.0023 (19)
C12	0.043 (2)	0.056 (3)	0.0365 (18)	0.007 (2)	0.0020 (19)	0.0021 (18)
N11	0.063 (3)	0.073 (3)	0.0394 (17)	−0.010 (3)	0.011 (2)	−0.0123 (17)
C13	0.047 (2)	0.055 (2)	0.0330 (17)	−0.011 (2)	0.0015 (18)	−0.0018 (17)
C14	0.049 (2)	0.071 (3)	0.042 (2)	0.003 (3)	0.001 (2)	−0.004 (2)
C15	0.054 (3)	0.098 (4)	0.058 (3)	−0.007 (3)	0.013 (3)	−0.018 (3)
C16	0.096 (5)	0.107 (5)	0.040 (2)	−0.041 (5)	0.020 (3)	−0.009 (3)
C17	0.122 (7)	0.096 (5)	0.055 (3)	−0.013 (5)	0.010 (4)	0.023 (3)
C18	0.074 (4)	0.067 (3)	0.059 (3)	−0.001 (3)	0.008 (3)	0.016 (2)

Geometric parameters (Å, º) top

Cl1—O3	1.33 (2)	N11—H11A	0.8900
Cl1—O1	1.37 (2)	N11—H11B	0.8900
Cl1—O2'	1.37 (2)	N11—H11C	0.8900
Cl1—O2	1.383 (19)	C13—C18	1.369 (7)
Cl1—O4'	1.409 (15)	C13—C14	1.375 (7)
Cl1—O1'	1.417 (19)	C14—C15	1.382 (7)
Cl1—O3'	1.44 (2)	C14—H14	0.9300
Cl1—O4	1.46 (2)	C15—C16	1.378 (9)
O1A—C11	1.184 (5)	C15—H15	0.9300
O1B—C11	1.287 (6)	C16—C17	1.367 (11)
O1B—H12	0.8200	C16—H16	0.9300
C11—C12	1.521 (6)	C17—C18	1.386 (8)
C12—N11	1.493 (5)	C17—H17	0.9300
C12—C13	1.514 (6)	C18—H18	0.9300
C12—H12A	0.9800

O3—Cl1—O1	106.7 (10)	O1B—C11—C12	111.4 (4)
O3—Cl1—O2'	117.6 (14)	N11—C12—C13	111.2 (4)
O1—Cl1—O2'	127.6 (16)	N11—C12—C11	106.9 (3)
O3—Cl1—O2	114.6 (16)	C13—C12—C11	113.2 (3)
O1—Cl1—O2	120.8 (16)	N11—C12—H12A	108.5
O2'—Cl1—O2	14 (2)	C13—C12—H12A	108.5
O3—Cl1—O4'	118.5 (16)	C11—C12—H12A	108.5
O1—Cl1—O4'	82.6 (11)	C12—N11—H11A	109.5
O2'—Cl1—O4'	98.4 (11)	C12—N11—H11B	109.5
O2—Cl1—O4'	110.2 (12)	H11A—N11—H11B	109.5
O3—Cl1—O1'	106.2 (13)	C12—N11—H11C	109.5
O1—Cl1—O1'	30.5 (8)	H11A—N11—H11C	109.5
O2'—Cl1—O1'	106.6 (15)	H11B—N11—H11C	109.5
O2—Cl1—O1'	95.9 (17)	C18—C13—C14	119.7 (5)
O4'—Cl1—O1'	108.6 (11)	C18—C13—C12	120.0 (5)
O3—Cl1—O3'	13 (2)	C14—C13—C12	120.3 (4)
O1—Cl1—O3'	111.2 (11)	C13—C14—C15	120.2 (5)
O2'—Cl1—O3'	107.0 (15)	C13—C14—H14	119.9
O2—Cl1—O3'	102.3 (14)	C15—C14—H14	119.9
O4'—Cl1—O3'	130.8 (13)	C16—C15—C14	119.6 (6)
O1'—Cl1—O3'	103.5 (11)	C16—C15—H15	120.2
O3—Cl1—O4	86.2 (18)	C14—C15—H15	120.2
O1—Cl1—O4	108.8 (14)	C17—C16—C15	120.4 (5)
O2'—Cl1—O4	101.0 (18)	C17—C16—H16	119.8
O2—Cl1—O4	114 (2)	C15—C16—H16	119.8
O4'—Cl1—O4	36.6 (10)	C16—C17—C18	119.5 (6)
O1'—Cl1—O4	139.1 (13)	C16—C17—H17	120.2
O3'—Cl1—O4	96.4 (16)	C18—C17—H17	120.2
C11—O1B—H12	109.5	C13—C18—C17	120.5 (6)
O1A—C11—O1B	127.5 (4)	C13—C18—H18	119.8
O1A—C11—C12	121.2 (4)	C17—C18—H18	119.8

O1A—C11—C12—N11	16.1 (6)	C18—C13—C14—C15	−0.5 (8)
O1B—C11—C12—N11	−164.9 (4)	C12—C13—C14—C15	178.2 (5)
O1A—C11—C12—C13	−106.8 (5)	C13—C14—C15—C16	0.4 (8)
O1B—C11—C12—C13	72.2 (5)	C14—C15—C16—C17	−0.3 (10)
N11—C12—C13—C18	94.3 (6)	C15—C16—C17—C18	0.5 (10)
C11—C12—C13—C18	−145.3 (5)	C14—C13—C18—C17	0.7 (8)
N11—C12—C13—C14	−84.4 (5)	C12—C13—C18—C17	−178.0 (5)
C11—C12—C13—C14	36.0 (6)	C16—C17—C18—C13	−0.6 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H12···O3ⁱ	0.82	1.97	2.78 (2)	168
O1B—H12···O3′ⁱ	0.82	1.94	2.76 (2)	178
N11—H11A···O2′ⁱⁱ	0.89	2.31	3.036 (17)	139
N11—H11A···O4′ⁱⁱ	0.89	2.45	3.297 (16)	159
N11—H11A···O2ⁱⁱ	0.89	2.60	3.29 (2)	136
N11—H11B···O2ⁱⁱⁱ	0.89	2.22	3.076 (17)	161
N11—H11B···O2′ⁱⁱⁱ	0.89	2.37	3.23 (2)	162
N11—H11C···O1	0.89	2.47	2.906 (18)	111
N11—H11C···O4′	0.89	2.63	3.44 (2)	153

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

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D-Phenyl­glycinium perchlorate

Supporting information

Key indicators

checkCIF results

D-Phenylglycinium perchlorate