2-Amino-6-(2,6-difluoro-benzamido)-pyridinium chloride.

In the cation of the title compound, C(12)H(10)F(2)N(3)O(+)·Cl(-), the dihedral angle between the pyridine and benzene rings is 16.1 (1)°. In the crystal structure, mol-ecules linked into two-dimensional sheets parallel to the bc plane by inter-molecular N-H⋯Cl, C-H⋯Cl and C-H⋯F hydrogen bonds.

Related literature

For general background to 2,6-diflorobenzyl­chloride derivatives, see: Beavo (1995 ▶); Beavo & Reifsnyder (1990 ▶); Hidaka & Asano (1976 ▶); Nicholson et al. (1991 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H10F2N3O+·Cl−

M = 285.68

Monoclinic,

a = 7.3196 (2) Å

b = 13.6314 (3) Å

c = 12.2892 (3) Å

β = 99.755 (1)°

V = 1208.44 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.34 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.895, T max = 0.972

11996 measured reflections

3524 independent reflections

2628 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 1.07

3524 reflections

188 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029624/lh5090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029624/lh5090Isup2.hkl

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

C12H10F2N3O+·Cl−	F(000) = 584
Mr = 285.68	Dx = 1.570 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3017 reflections
a = 7.3196 (2) Å	θ = 3.4–30.0°
b = 13.6314 (3) Å	µ = 0.34 mm−1
c = 12.2892 (3) Å	T = 100 K
β = 99.755 (1)°	Needle, green
V = 1208.44 (5) Å3	0.34 × 0.12 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3524 independent reflections
Radiation source: fine-focus sealed tube	2628 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→10
Tmin = 0.895, Tmax = 0.972	k = −15→19
11996 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.7252P] where P = (Fo2 + 2Fc2)/3
3524 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.00538 (7)	0.25071 (3)	0.48845 (3)	0.02010 (13)
F1	0.25530 (18)	0.41301 (9)	0.78112 (10)	0.0280 (3)
F2	0.45736 (17)	0.69690 (9)	0.61851 (10)	0.0250 (3)
O1	0.3723 (2)	0.41722 (10)	0.57487 (11)	0.0235 (3)
N1	0.2196 (2)	0.55280 (13)	0.49862 (13)	0.0179 (3)
N2	0.1692 (2)	0.42610 (12)	0.36587 (13)	0.0174 (3)
N3	0.1129 (3)	0.29372 (13)	0.24827 (14)	0.0212 (4)
C1	0.3195 (3)	0.50617 (15)	0.78901 (16)	0.0209 (4)
C2	0.3485 (3)	0.55016 (18)	0.89145 (16)	0.0267 (5)
H2A	0.3219	0.5170	0.9530	0.032*
C3	0.4181 (3)	0.64466 (18)	0.90068 (17)	0.0284 (5)
H3A	0.4396	0.6750	0.9695	0.034*
C4	0.4564 (3)	0.69494 (16)	0.80912 (17)	0.0245 (4)
H4A	0.5063	0.7578	0.8156	0.029*
C5	0.4181 (3)	0.64856 (15)	0.70798 (16)	0.0193 (4)
C6	0.3492 (3)	0.55372 (14)	0.69319 (15)	0.0175 (4)
C7	0.3170 (3)	0.50038 (14)	0.58476 (15)	0.0176 (4)
C8	0.1933 (3)	0.52380 (14)	0.38828 (15)	0.0164 (4)
C9	0.1878 (3)	0.58888 (15)	0.30421 (16)	0.0195 (4)
H9A	0.2019	0.6557	0.3187	0.023*
C10	0.1605 (3)	0.55403 (15)	0.19510 (16)	0.0208 (4)
H10A	0.1580	0.5981	0.1371	0.025*
C11	0.1375 (3)	0.45590 (15)	0.17297 (15)	0.0188 (4)
H11A	0.1215	0.4333	0.1006	0.023*
C12	0.1384 (3)	0.38928 (14)	0.26127 (14)	0.0164 (4)
H1N1	0.181 (3)	0.6086 (19)	0.512 (2)	0.031 (7)*
H1N2	0.166 (3)	0.3855 (18)	0.420 (2)	0.027 (6)*
H1N3	0.095 (3)	0.2722 (18)	0.183 (2)	0.030 (7)*
H2N3	0.105 (3)	0.2579 (18)	0.303 (2)	0.025 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0327 (3)	0.0136 (2)	0.01412 (19)	0.00100 (19)	0.00408 (17)	0.00081 (17)
F1	0.0345 (7)	0.0215 (7)	0.0282 (6)	−0.0066 (5)	0.0053 (5)	0.0033 (5)
F2	0.0321 (7)	0.0177 (6)	0.0235 (6)	−0.0045 (5)	−0.0004 (5)	0.0025 (5)
O1	0.0313 (8)	0.0155 (7)	0.0210 (7)	0.0069 (6)	−0.0038 (6)	−0.0023 (6)
N1	0.0250 (9)	0.0120 (8)	0.0155 (7)	0.0029 (7)	0.0005 (6)	−0.0011 (6)
N2	0.0245 (9)	0.0145 (8)	0.0130 (7)	−0.0002 (7)	0.0027 (6)	0.0010 (6)
N3	0.0359 (10)	0.0154 (9)	0.0124 (7)	−0.0024 (7)	0.0048 (7)	−0.0008 (7)
C1	0.0200 (10)	0.0200 (11)	0.0222 (9)	0.0002 (8)	0.0020 (8)	0.0003 (8)
C2	0.0256 (11)	0.0372 (13)	0.0173 (9)	0.0028 (10)	0.0037 (8)	−0.0016 (9)
C3	0.0273 (12)	0.0364 (13)	0.0205 (9)	0.0056 (10)	0.0009 (8)	−0.0120 (9)
C4	0.0244 (11)	0.0202 (11)	0.0271 (10)	0.0047 (8)	−0.0011 (8)	−0.0085 (8)
C5	0.0214 (10)	0.0160 (10)	0.0193 (9)	0.0018 (8)	0.0006 (7)	−0.0013 (7)
C6	0.0189 (9)	0.0160 (10)	0.0166 (8)	0.0025 (7)	−0.0002 (7)	−0.0019 (7)
C7	0.0181 (9)	0.0167 (10)	0.0170 (8)	−0.0012 (8)	0.0003 (7)	−0.0007 (7)
C8	0.0175 (9)	0.0148 (10)	0.0159 (8)	0.0007 (7)	0.0001 (7)	−0.0025 (7)
C9	0.0244 (10)	0.0127 (10)	0.0208 (9)	−0.0005 (8)	0.0019 (8)	0.0008 (7)
C10	0.0255 (10)	0.0183 (10)	0.0180 (8)	−0.0001 (8)	0.0025 (8)	0.0046 (8)
C11	0.0233 (10)	0.0199 (10)	0.0130 (8)	−0.0012 (8)	0.0024 (7)	−0.0005 (7)
C12	0.0186 (9)	0.0152 (9)	0.0150 (8)	0.0007 (7)	0.0017 (7)	−0.0007 (7)

F1—C1	1.352 (2)	C2—H2A	0.9300
F2—C5	1.354 (2)	C3—C4	1.386 (3)
O1—C7	1.217 (2)	C3—H3A	0.9300
N1—C7	1.373 (2)	C4—C5	1.380 (3)
N1—C8	1.394 (2)	C4—H4A	0.9300
N1—H1N1	0.84 (3)	C5—C6	1.388 (3)
N2—C12	1.363 (2)	C6—C7	1.501 (3)
N2—C8	1.365 (2)	C8—C9	1.357 (3)
N2—H1N2	0.87 (2)	C9—C10	1.405 (3)
N3—C12	1.322 (3)	C9—H9A	0.9300
N3—H1N3	0.84 (3)	C10—C11	1.370 (3)
N3—H2N3	0.84 (2)	C10—H10A	0.9300
C1—C2	1.378 (3)	C11—C12	1.414 (3)
C1—C6	1.393 (3)	C11—H11A	0.9300
C2—C3	1.383 (3)
C7—N1—C8	124.78 (17)	C4—C5—C6	123.94 (19)
C7—N1—H1N1	117.9 (17)	C5—C6—C1	115.33 (17)
C8—N1—H1N1	117.0 (17)	C5—C6—C7	124.48 (17)
C12—N2—C8	123.00 (16)	C1—C6—C7	120.10 (18)
C12—N2—H1N2	117.7 (16)	O1—C7—N1	123.10 (18)
C8—N2—H1N2	119.2 (16)	O1—C7—C6	122.36 (17)
C12—N3—H1N3	117.0 (17)	N1—C7—C6	114.54 (17)
C12—N3—H2N3	120.1 (16)	C9—C8—N2	119.86 (17)
H1N3—N3—H2N3	123 (2)	C9—C8—N1	122.45 (18)
F1—C1—C2	118.17 (18)	N2—C8—N1	117.68 (16)
F1—C1—C6	118.59 (17)	C8—C9—C10	119.13 (18)
C2—C1—C6	123.2 (2)	C8—C9—H9A	120.4
C1—C2—C3	118.5 (2)	C10—C9—H9A	120.4
C1—C2—H2A	120.7	C11—C10—C9	120.84 (18)
C3—C2—H2A	120.7	C11—C10—H10A	119.6
C2—C3—C4	121.09 (19)	C9—C10—H10A	119.6
C2—C3—H3A	119.5	C10—C11—C12	119.36 (17)
C4—C3—H3A	119.5	C10—C11—H11A	120.3
C5—C4—C3	117.8 (2)	C12—C11—H11A	120.3
C5—C4—H4A	121.1	N3—C12—N2	118.32 (17)
C3—C4—H4A	121.1	N3—C12—C11	123.91 (17)
F2—C5—C4	118.02 (18)	N2—C12—C11	117.77 (17)
F2—C5—C6	117.99 (16)
F1—C1—C2—C3	178.58 (19)	C5—C6—C7—O1	131.1 (2)
C6—C1—C2—C3	−2.9 (3)	C1—C6—C7—O1	−45.2 (3)
C1—C2—C3—C4	0.7 (3)	C5—C6—C7—N1	−49.3 (3)
C2—C3—C4—C5	1.7 (3)	C1—C6—C7—N1	134.4 (2)
C3—C4—C5—F2	−179.22 (18)	C12—N2—C8—C9	−0.2 (3)
C3—C4—C5—C6	−2.1 (3)	C12—N2—C8—N1	178.56 (18)
F2—C5—C6—C1	177.18 (17)	C7—N1—C8—C9	−144.7 (2)
C4—C5—C6—C1	0.1 (3)	C7—N1—C8—N2	36.5 (3)
F2—C5—C6—C7	0.7 (3)	N2—C8—C9—C10	−1.2 (3)
C4—C5—C6—C7	−176.40 (19)	N1—C8—C9—C10	−179.89 (18)
F1—C1—C6—C5	−178.98 (17)	C8—C9—C10—C11	0.8 (3)
C2—C1—C6—C5	2.5 (3)	C9—C10—C11—C12	1.0 (3)
F1—C1—C6—C7	−2.4 (3)	C8—N2—C12—N3	−178.62 (18)
C2—C1—C6—C7	179.1 (2)	C8—N2—C12—C11	2.0 (3)
C8—N1—C7—O1	−9.0 (3)	C10—C11—C12—N3	178.30 (19)
C8—N1—C7—C6	171.45 (18)	C10—C11—C12—N2	−2.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···Cl1i	0.84 (3)	2.35 (2)	3.1622 (18)	163 (2)
N2—H1N2···Cl1	0.87 (2)	2.41 (2)	3.1678 (17)	146 (2)
N3—H1N3···Cl1ii	0.84 (2)	2.39 (2)	3.2140 (17)	166 (2)
N3—H2N3···Cl1	0.84 (2)	2.51 (2)	3.2346 (18)	145 (2)
C3—H3A···F2iii	0.93	2.52	3.414 (3)	162
C10—H10A···Cl1iv	0.93	2.74	3.581 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯Cl1i	0.84 (3)	2.35 (2)	3.1622 (18)	163 (2)
N2—H1N2⋯Cl1	0.87 (2)	2.41 (2)	3.1678 (17)	146 (2)
N3—H1N3⋯Cl1ii	0.84 (2)	2.39 (2)	3.2140 (17)	166 (2)
N3—H2N3⋯Cl1	0.84 (2)	2.51 (2)	3.2346 (18)	145 (2)
C3—H3A⋯F2iii	0.93	2.52	3.414 (3)	162
C10—H10A⋯Cl1iv	0.93	2.74	3.581 (2)	151

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