l-Leucinium fluoride monohydrate.

The asymmetric unit of the title hydrated salt, C(6)H(14)NO(2) (+)·F(-)·H(2)O, contains a discrete cation with a protonated amino group, a halide anion and one water mol-ecule. The crystal structure is composed of double layers parallel to (010) held together by N-H⋯O, N-H⋯F, O-H⋯F and C-H⋯F hydrogen bonds, forming a two-dimensional network, and stacked along the c axis, viz. hydro-philic layers at z = 0 and 1/2 and hydro-phobic layers at z = 1/3 and 2/3.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to carb­oxy­lic acids, see: Miller & Orgel (1974 ▶); Kvenvolden et al. (1971 ▶). For our research on organic salts of amino acids, see: Guenifa et al. (2009 ▶); Moussa Slimane et al. (2009 ▶). For l-leucinium oxalate, see: Rajagopal et al. (2003 ▶) and for l-leucinium perchlorate, see: Janczak & Perpétuo (2007 ▶).

Experimental

Crystal data

C6H14NO2 +·F−·H2O

M = 169.20

Orthorhombic,

a = 5.7058 (1) Å

b = 5.8289 (1) Å

c = 27.3150 (4) Å

V = 908.46 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.3 × 0.03 × 0.02 mm

Data collection

Oxford Diffraction Super Nova diffractometer with an Atlas detector

27972 measured reflections

2771 independent reflections

2584 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.078

S = 1.06

2771 reflections

118 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶), Mercury (Macrae et al., 2006 ▶) and POVRay (Persistence of Vision Team, 2004 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039001/aa2065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039001/aa2065Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039001/aa2065Isup3.cml

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

C6H14NO2+·F−·H2O	F(000) = 368
Mr = 169.20	Dx = 1.237 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 27972 reflections
a = 5.7058 (1) Å	θ = 3.6–30.5°
b = 5.8289 (1) Å	µ = 0.11 mm−1
c = 27.3150 (4) Å	T = 100 K
V = 908.46 (3) Å3	Needle, colourless
Z = 4	0.3 × 0.03 × 0.02 mm

Oxford Diffraction Super Nova diffractometer with an Atlas detector	2584 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.039
Graphite monochromator	θmax = 30.5°, θmin = 3.6°
Detector resolution: 10.4508 pixels mm-1	h = −8→8
ω scans	k = −8→8
27972 measured reflections	l = −39→39
2771 independent reflections

Refinement on F2	7 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.045P)2 + 0.0976P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.28 e Å−3
2771 reflections	Δρmin = −0.14 e Å−3
118 parameters

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
F1	0.01929 (10)	0.16104 (10)	0.56810 (2)	0.01618 (13)
O1	−0.18388 (14)	1.11050 (12)	0.38989 (3)	0.01957 (16)
O1W	0.35872 (12)	0.05014 (12)	0.50292 (3)	0.01595 (15)
H1W	0.248 (2)	0.090 (2)	0.5214 (4)	0.024*
H2W	0.404 (2)	0.152 (2)	0.4837 (4)	0.024*
O2	−0.16963 (15)	0.93446 (14)	0.46240 (3)	0.02415 (18)
N1	0.20572 (15)	0.68869 (14)	0.44249 (3)	0.01236 (15)
C2	0.10845 (16)	0.82520 (16)	0.40113 (3)	0.01163 (16)
H2	0.2288	0.9319	0.3894	0.014*
C3	0.02982 (17)	0.67306 (17)	0.35844 (3)	0.01419 (17)
H3B	−0.0459	0.7694	0.3342	0.017*
H3A	−0.0867	0.5658	0.3705	0.017*
C1	−0.09782 (17)	0.96280 (16)	0.42137 (3)	0.01297 (17)
C4	0.2246 (2)	0.5363 (2)	0.33310 (4)	0.0212 (2)
H4	0.3018	0.4393	0.3576	0.025*
C5	0.1160 (2)	0.38189 (19)	0.29402 (4)	0.0269 (2)
H5A	0.2373	0.296	0.278	0.04*
H5C	0.0351	0.4746	0.2704	0.04*
H5B	0.0072	0.278	0.3091	0.04*
C6	0.4082 (2)	0.6941 (3)	0.31019 (5)	0.0349 (3)
H6A	0.4746	0.7906	0.3351	0.052*
H6B	0.3356	0.7877	0.2856	0.052*
H6C	0.5297	0.6032	0.2955	0.052*
H1	−0.294 (3)	1.184 (3)	0.4060 (7)	0.052*
H2N	0.317 (3)	0.593 (3)	0.4337 (6)	0.042*
H1N	0.090 (3)	0.610 (3)	0.4578 (6)	0.042*
H3N	0.263 (3)	0.784 (3)	0.4649 (5)	0.042*

	U11	U22	U33	U12	U13	U23
F1	0.0160 (3)	0.0144 (3)	0.0181 (3)	−0.0065 (2)	0.0001 (2)	0.0000 (2)
O1	0.0231 (4)	0.0191 (3)	0.0164 (3)	0.0124 (3)	0.0043 (3)	0.0044 (3)
O1W	0.0147 (3)	0.0115 (3)	0.0216 (3)	0.0002 (3)	0.0031 (3)	0.0007 (3)
O2	0.0285 (4)	0.0232 (4)	0.0207 (4)	0.0140 (3)	0.0102 (3)	0.0085 (3)
N1	0.0130 (4)	0.0112 (3)	0.0129 (3)	0.0033 (3)	0.0003 (3)	0.0004 (3)
C2	0.0121 (4)	0.0102 (3)	0.0126 (4)	0.0032 (3)	0.0014 (3)	0.0015 (3)
C3	0.0152 (4)	0.0143 (4)	0.0130 (4)	0.0026 (4)	−0.0006 (3)	−0.0015 (3)
C1	0.0136 (4)	0.0093 (4)	0.0160 (4)	0.0023 (3)	0.0007 (3)	−0.0001 (3)
C4	0.0251 (5)	0.0235 (5)	0.0149 (4)	0.0123 (4)	−0.0013 (4)	−0.0040 (4)
C5	0.0398 (6)	0.0215 (5)	0.0193 (5)	0.0034 (5)	0.0028 (5)	−0.0061 (4)
C6	0.0188 (5)	0.0536 (8)	0.0322 (6)	−0.0022 (5)	0.0076 (5)	−0.0192 (6)

O1—C1	1.3121 (12)	C4—C5	1.5276 (16)
O2—C1	1.2047 (12)	C4—C6	1.5281 (18)
O1—H1	0.879 (18)	C2—H2	0.9800
O1W—H1W	0.841 (11)	C3—H3B	0.9700
O1W—H2W	0.834 (11)	C3—H3A	0.9700
N1—C2	1.4891 (12)	C4—H4	0.9800
N1—H2N	0.879 (17)	C5—H5B	0.9600
N1—H3N	0.889 (16)	C5—H5C	0.9600
N1—H1N	0.906 (17)	C5—H5A	0.9600
C1—C2	1.5278 (13)	C6—H6C	0.9600
C2—C3	1.5321 (12)	C6—H6A	0.9600
C3—C4	1.5329 (15)	C6—H6B	0.9600
C1—O1—H1	105.0 (12)	C2—C3—H3A	108.00
H1W—O1W—H2W	114.5 (11)	C2—C3—H3B	108.00
H2N—N1—H3N	108.6 (16)	C4—C3—H3B	108.00
H1N—N1—H3N	105.5 (15)	H3A—C3—H3B	107.00
C2—N1—H1N	110.4 (11)	C4—C3—H3A	108.00
C2—N1—H2N	113.7 (11)	C5—C4—H4	109.00
C2—N1—H3N	109.0 (10)	C6—C4—H4	109.00
H1N—N1—H2N	109.4 (16)	C3—C4—H4	109.00
O1—C1—O2	124.92 (9)	C4—C5—H5A	109.00
O2—C1—C2	121.78 (8)	C4—C5—H5B	110.00
O1—C1—C2	113.30 (7)	H5A—C5—H5B	109.00
N1—C2—C3	112.16 (8)	H5A—C5—H5C	110.00
C1—C2—C3	110.71 (7)	C4—C5—H5C	109.00
N1—C2—C1	107.04 (7)	H5B—C5—H5C	109.00
C2—C3—C4	115.62 (8)	C4—C6—H6B	109.00
C3—C4—C5	109.14 (9)	C4—C6—H6C	110.00
C3—C4—C6	111.65 (10)	C4—C6—H6A	109.00
C5—C4—C6	110.28 (10)	H6A—C6—H6C	110.00
N1—C2—H2	109.00	H6B—C6—H6C	109.00
C3—C2—H2	109.00	H6A—C6—H6B	109.00
C1—C2—H2	109.00
O1—C1—C2—N1	172.87 (8)	N1—C2—C3—C4	−63.80 (10)
O1—C1—C2—C3	−64.60 (10)	C1—C2—C3—C4	176.70 (8)
O2—C1—C2—N1	−6.99 (12)	C2—C3—C4—C5	176.10 (8)
O2—C1—C2—C3	115.54 (10)	C2—C3—C4—C6	−61.73 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1Wi	0.91 (2)	1.94 (2)	2.8428 (11)	174 (2)
N1—H2N···F1ii	0.879 (17)	1.878 (17)	2.7277 (10)	162.1 (16)
N1—H3N···O1Wiii	0.89 (2)	1.95 (2)	2.8152 (11)	166 (2)
O1—H1···F1iv	0.88 (2)	1.57 (2)	2.4410 (10)	174 (2)
O1W—H1W···F1	0.84 (1)	1.87 (1)	2.7090 (9)	174 (1)
O1W—H2W···F1ii	0.83 (1)	1.90 (1)	2.7271 (9)	170 (1)
C4—H4···F1ii	0.98	2.45	3.3813 (12)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1W i	0.91 (2)	1.94 (2)	2.8428 (11)	174 (2)
N1—H2N⋯F1ii	0.879 (17)	1.878 (17)	2.7277 (10)	162.1 (16)
N1—H3N⋯O1W iii	0.89 (2)	1.95 (2)	2.8152 (11)	166 (2)
O1—H1⋯F1iv	0.88 (2)	1.57 (2)	2.4410 (10)	174 (2)
O1W—H1W⋯F1	0.84 (1)	1.87 (1)	2.7090 (9)	174 (1)
O1W—H2W⋯F1ii	0.83 (1)	1.90 (1)	2.7271 (9)	170 (1)
C4—H4⋯F1ii	0.98	2.45	3.3813 (12)	159

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