2-(4-Amino-phen-yl)-3,4,5,6-tetra-hydro-pyrimidin-1-ium chloride.

In the title compound, C(10)H(14)N(3) (+)·Cl(-), the tetra-hydro-pyridinium ring of the cation, which adopts a slightly distorted envelope conformation, is disordered over two orientations with an occupancy ratio of 0.653 (5):0.347 (5). The amidinium fragment of the major conformer is twisted relative to the benzene ring by 22.5 (6)° and the two C-N bond lengths of this fragment are similar [1.3228 (16) and 1.319 (2) Å]. In the crystal, the chloride anions are involved in three N-H⋯Cl hydrogen bonds, which link the components into a two-dimensional hydrogen-bonded network parallel to (010).

Related literature

For the synthesis, see: Wydra et al. (1990 ▶); Stolić et al. (2009 ▶, 2011 ▶). For related compounds, see: Molčanov et al. (2011 ▶); Jarak et al. (2005 ▶); Legrand et al. (2008 ▶). For the biological activity of compounds comprising a cyclic amidine system, see: Boykin (2002 ▶); Chaires et al. (2004 ▶); Farahat et al. (2011 ▶); Hall et al. (1998 ▶). For the GAMESS program package, see: Schmidt et al. (1993 ▶).

Experimental

Crystal data

C10H14N3 +·Cl−

M = 211.69

Orthorhombic,

a = 15.0055 (2) Å

b = 8.0884 (1) Å

c = 17.8088 (3) Å

V = 2161.46 (5) Å3

Z = 8

Cu Kα radiation

μ = 2.84 mm−1

T = 293 K

0.15 × 0.10 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur Nova R diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.676, T max = 0.784

6131 measured reflections

2242 independent reflections

1760 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.098

S = 1.05

2242 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014493/gk2441sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014493/gk2441Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014493/gk2441Isup3.cml

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

C10H14N3+·Cl−	F(000) = 896
Mr = 211.69	Dx = 1.301 Mg m−3
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3458 reflections
a = 15.0055 (2) Å	θ = 2.5–76.0°
b = 8.0884 (1) Å	µ = 2.84 mm−1
c = 17.8088 (3) Å	T = 293 K
V = 2161.46 (5) Å3	Prism, colourless
Z = 8	0.15 × 0.10 × 0.09 mm

Oxford Diffraction Xcalibur Nova R diffractometer	1760 reflections with I > 2σ(I)
ω scans	Rint = 0.017
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	θmax = 76.2°, θmin = 5.0°
Tmin = 0.676, Tmax = 0.784	h = −18→18
6131 measured reflections	k = −5→10
2242 independent reflections	l = −22→22

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.0224P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.18 e Å−3
2242 reflections	Δρmin = −0.16 e Å−3
146 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.33023 (2)	0.24010 (5)	0.60412 (2)	0.05806 (15)
N1	0.73148 (10)	0.50143 (18)	0.76130 (9)	0.0710 (4)
H1NB	0.7775	0.5727	0.7593	0.085*
H1NA	0.7154	0.4539	0.8049	0.085*
N2A	0.48706 (7)	0.24901 (14)	0.48980 (7)	0.0481 (3)	0.347 (5)
H2NB	0.4516	0.2692	0.5296	0.058*	0.347 (5)
N2B	0.48706 (7)	0.24901 (14)	0.48980 (7)	0.0481 (3)	0.653 (5)
H2N	0.4516	0.2691	0.5295	0.058*	0.653 (5)
N3A	0.6227 (6)	0.2596 (6)	0.4311 (5)	0.0498 (10)	0.653 (5)
H3M	0.682	0.2722	0.4359	0.06*	0.653 (5)
N3B	0.6181 (11)	0.3005 (15)	0.4279 (11)	0.0498 (10)	0.347 (5)
H3N	0.6774	0.3132	0.4327	0.06*	0.347 (5)
C1	0.69335 (9)	0.45272 (15)	0.69569 (8)	0.0474 (3)
C2	0.61748 (9)	0.35056 (16)	0.69653 (7)	0.0475 (3)
H2	0.5937	0.3163	0.7422	0.057*
C3	0.57817 (8)	0.30093 (16)	0.63062 (7)	0.0436 (3)
H3	0.5275	0.2348	0.6323	0.052*
C4	0.61292 (8)	0.34788 (14)	0.56100 (7)	0.0405 (3)
C5	0.68797 (9)	0.45061 (16)	0.56016 (8)	0.0483 (3)
H5	0.712	0.4839	0.5145	0.058*
C6	0.72660 (10)	0.50288 (16)	0.62576 (9)	0.0510 (3)
H6	0.7757	0.5729	0.6238	0.061*
C7A	0.57250 (8)	0.28921 (15)	0.49100 (7)	0.0427 (3)	0.347 (5)
C7B	0.57250 (8)	0.28921 (15)	0.49100 (7)	0.0427 (3)	0.653 (5)
C8A	0.4451 (10)	0.2003 (13)	0.4167 (7)	0.0457 (8)	0.347 (5)
H8A1	0.4026	0.2777	0.3957	0.055*	0.347 (5)
H8A2	0.4127	0.1021	0.4324	0.055*	0.347 (5)
C8B	0.4427 (5)	0.1637 (5)	0.4285 (3)	0.0457 (8)	0.653 (5)
H8A	0.446	0.0442	0.432	0.055*	0.653 (5)
H8B	0.3803	0.1951	0.4276	0.055*	0.653 (5)
C9A	0.5137 (3)	0.1287 (7)	0.3654 (2)	0.0539 (14)	0.347 (5)
H9A1	0.5428	0.0266	0.3802	0.065*	0.347 (5)
H9A2	0.4832	0.1087	0.3183	0.065*	0.347 (5)
C9B	0.48604 (17)	0.2297 (4)	0.35639 (14)	0.0574 (8)	0.653 (5)
H9B1	0.475	0.3468	0.3492	0.069*	0.653 (5)
H9B2	0.4611	0.1709	0.3138	0.069*	0.653 (5)
C10A	0.5833 (7)	0.2609 (10)	0.3539 (6)	0.0575 (9)	0.347 (5)
H10C	0.6269	0.2273	0.3167	0.069*	0.347 (5)
H10D	0.5567	0.3649	0.3386	0.069*	0.347 (5)
C10B	0.5866 (3)	0.1982 (5)	0.3599 (3)	0.0575 (9)	0.653 (5)
H10A	0.5985	0.0804	0.3593	0.069*	0.653 (5)
H10B	0.6159	0.2482	0.317	0.069*	0.653 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0367 (2)	0.0877 (3)	0.0498 (2)	−0.00153 (14)	0.00414 (13)	0.00525 (16)
N1	0.0747 (9)	0.0785 (8)	0.0598 (8)	−0.0183 (7)	−0.0182 (7)	−0.0077 (6)
N2A	0.0334 (5)	0.0656 (7)	0.0454 (6)	0.0000 (4)	0.0010 (5)	−0.0087 (5)
N2B	0.0334 (5)	0.0656 (7)	0.0454 (6)	0.0000 (4)	0.0010 (5)	−0.0087 (5)
N3A	0.0340 (10)	0.069 (3)	0.0461 (10)	0.005 (2)	0.0034 (8)	−0.006 (2)
N3B	0.0340 (10)	0.069 (3)	0.0461 (10)	0.005 (2)	0.0034 (8)	−0.006 (2)
C1	0.0431 (6)	0.0459 (6)	0.0533 (7)	0.0034 (5)	−0.0080 (6)	−0.0059 (5)
C2	0.0433 (7)	0.0561 (7)	0.0430 (6)	−0.0005 (5)	0.0012 (6)	−0.0006 (6)
C3	0.0350 (6)	0.0488 (6)	0.0470 (7)	−0.0029 (5)	0.0009 (5)	−0.0013 (5)
C4	0.0322 (5)	0.0453 (6)	0.0440 (6)	0.0024 (4)	0.0000 (5)	−0.0004 (5)
C5	0.0407 (6)	0.0529 (7)	0.0515 (7)	−0.0045 (5)	0.0037 (6)	0.0042 (5)
C6	0.0395 (6)	0.0508 (7)	0.0627 (8)	−0.0083 (5)	−0.0033 (6)	−0.0019 (6)
C7A	0.0354 (6)	0.0495 (6)	0.0433 (6)	0.0037 (5)	0.0008 (5)	−0.0003 (5)
C7B	0.0354 (6)	0.0495 (6)	0.0433 (6)	0.0037 (5)	0.0008 (5)	−0.0003 (5)
C8A	0.0416 (7)	0.050 (2)	0.0454 (19)	−0.0047 (19)	−0.0044 (13)	0.0034 (14)
C8B	0.0416 (7)	0.050 (2)	0.0454 (19)	−0.0047 (19)	−0.0044 (13)	0.0034 (14)
C9A	0.052 (3)	0.061 (3)	0.049 (2)	0.005 (2)	−0.0064 (19)	−0.0088 (19)
C9B	0.0558 (14)	0.0712 (18)	0.0453 (12)	0.0074 (12)	−0.0077 (10)	−0.0036 (11)
C10A	0.0534 (10)	0.077 (3)	0.0425 (11)	0.004 (2)	0.0041 (9)	−0.007 (2)
C10B	0.0534 (10)	0.077 (3)	0.0425 (11)	0.004 (2)	0.0041 (9)	−0.007 (2)

N1—C1	1.3593 (18)	C4—C5	1.3996 (17)
N1—H1NB	0.8999	C4—C7A	1.4653 (17)
N1—H1NA	0.8999	C5—C6	1.3710 (19)
N2A—C7A	1.3228 (17)	C5—H5	0.93
N2A—C8A	1.499 (14)	C6—H6	0.93
N2A—H2NB	0.901	C8A—C9A	1.494 (15)
N2B—H2N	0.9	C8A—H8A1	0.9677
N2B—C7B	1.3228 (16)	C8A—H8A2	0.9717
N2B—C8B	1.453 (6)	C8B—C9B	1.535 (6)
N3A—C7A	1.327 (9)	C8B—H8A	0.97
N3A—C10A	1.497 (14)	C8B—H8B	0.97
N3A—H3M	0.8999	C9A—C10A	1.509 (11)
N3B—C10B	1.541 (19)	C9A—H9A1	0.97
N3B—C7B	1.319 (2)	C9A—H9A2	0.97
N3B—H3N	0.8999	C9B—C10B	1.531 (6)
C1—C6	1.402 (2)	C9B—H9B1	0.97
C1—C2	1.4069 (19)	C10A—H10C	0.97
C2—C3	1.3736 (18)	C10A—H10D	0.97
C2—H2	0.93	C10B—H10A	0.97
C3—C4	1.3975 (18)	C10B—H10B	0.97
C3—H3	0.93
C1—N1—H1NB	118.4	C10A—C9A—H9A2	109.1
C1—N1—H1NA	120.4	H9A1—C9A—H9A2	107.8
H1NB—N1—H1NA	120.9	C8A—C9A—H9B2	84.7
C7A—N2A—C8A	119.1 (6)	C10A—C9A—H9B2	98.2
C7A—N2A—H2NB	121	H9A1—C9A—H9B2	135.3
C8A—N2A—H2NB	118.8	C8A—C9A—H10A	145.1
C7A—N2A—H2N	121	C10A—C9A—H10A	62.4
C8A—N2A—H2N	118.8	H9A1—C9A—H10A	49
C7A—N3A—C10A	120.9 (7)	H9A2—C9A—H10A	109.4
C7A—N3A—H3M	117.6	H9B2—C9A—H10A	128.2
C10A—N3A—H3M	118.5	C10B—C9B—C8B	109.0 (4)
C7A—N3A—H3N	113.1	C10B—C9B—H8A1	148.6
C10A—N3A—H3N	111.9	C8B—C9B—H8A1	48.7
C10B—N3B—H3M	106.6	C10B—C9B—H9A2	85.5
C10B—N3B—H3N	116.1	C8B—C9B—H9A2	100.1
N1—C1—C6	122.01 (13)	H8A1—C9B—H9A2	116.9
N1—C1—C2	120.11 (13)	C10B—C9B—H9B1	109.6
C6—C1—C2	117.87 (12)	C8B—C9B—H9B1	112.2
C3—C2—C1	120.67 (12)	H8A1—C9B—H9B1	70.4
C3—C2—H2	119.7	H9A2—C9B—H9B1	136.1
C1—C2—H2	119.7	C10B—C9B—H9B2	109.3
C2—C3—C4	121.22 (12)	C8B—C9B—H9B2	108.6
C2—C3—H3	119.4	H8A1—C9B—H9B2	99.8
C4—C3—H3	119.4	H9B1—C9B—H9B2	108.1
C3—C4—C5	118.10 (11)	C10B—C9B—H10D	56.9
C3—C4—C7A	120.81 (11)	C8B—C9B—H10D	134.7
C5—C4—C7A	121.08 (11)	H8A1—C9B—H10D	119.1
C6—C5—C4	120.94 (12)	H9A2—C9B—H10D	119.1
C6—C5—H5	119.5	H9B1—C9B—H10D	53.3
C4—C5—H5	119.5	H9B2—C9B—H10D	116.7
C5—C6—C1	121.16 (12)	N3A—C10A—C9A	98.2 (6)
C5—C6—H6	119.4	N3A—C10A—H10C	111.1
C1—C6—H6	119.4	C9A—C10A—H10C	111.2
N2A—C7A—N3A	119.5 (4)	N3A—C10A—H10D	115.2
N2A—C7A—C4	119.64 (12)	C9A—C10A—H10D	111.6
N3A—C7A—C4	120.5 (4)	H10C—C10A—H10D	109.3
C9A—C8A—N2A	110.1 (10)	N3A—C10A—H10A	82.6
C9A—C8A—H8A1	117.9	C9A—C10A—H10A	53
N2A—C8A—H8A1	116.2	H10C—C10A—H10A	70.4
C9A—C8A—H8A2	101.8	H10D—C10A—H10A	159.5
N2A—C8A—H8A2	100	N3A—C10A—H10B	119.8
H8A1—C8A—H8A2	108.1	C9A—C10A—H10B	115.4
C9A—C8A—H8A	75.1	H10D—C10A—H10B	97.5
N2A—C8A—H8A	94	H10A—C10A—H10B	80.6
H8A1—C8A—H8A	136.1	C9B—C10B—N3B	104.2 (7)
C9A—C8A—H8B	141.2	C9B—C10B—H9A1	75.3
N2A—C8A—H8B	104.6	N3B—C10B—H9A1	114.9
H8A1—C8A—H8B	57.2	C9B—C10B—H10C	121.5
H8A2—C8A—H8B	54.5	N3B—C10B—H10C	106.9
H8A—C8A—H8B	85.9	H9A1—C10B—H10C	129.1
C9B—C8B—H8A1	63.6	C9B—C10B—H10D	62.4
C9B—C8B—H8A2	128.9	N3B—C10B—H10D	78.7
H8A1—C8B—H8A2	105.9	H9A1—C10B—H10D	137.7
C9B—C8B—H8A	112.3	H10C—C10B—H10D	76.8
H8A1—C8B—H8A	142.5	C9B—C10B—H10A	110.2
C9B—C8B—H8B	107.8	N3B—C10B—H10A	118.6
H8A1—C8B—H8B	48.2	H10C—C10B—H10A	96.3
H8A2—C8B—H8B	63.4	H10D—C10B—H10A	162.7
H8A—C8B—H8B	108.2	C9B—C10B—H10B	110.2
C8A—C9A—C10A	106.6 (7)	N3B—C10B—H10B	104.8
C8A—C9A—H9A1	118.3	H9A1—C10B—H10B	137.3
C10A—C9A—H9A1	109.2	H10D—C10B—H10B	63.5
C8A—C9A—H9A2	105.5	H10A—C10B—H10B	108.4
N1—C1—C2—C3	179.79 (13)	C10A—N3A—C7A—N2A	29.8 (6)
C6—C1—C2—C3	0.59 (19)	C10A—N3A—C7A—C4	−157.3 (5)
C1—C2—C3—C4	1.0 (2)	C3—C4—C7A—N2A	26.62 (18)
C2—C3—C4—C5	−1.51 (19)	C5—C4—C7A—N2A	−154.22 (12)
C2—C3—C4—C7A	177.68 (12)	C3—C4—C7A—N3A	−146.3 (3)
C3—C4—C5—C6	0.38 (19)	C5—C4—C7A—N3A	32.9 (3)
C7A—C4—C5—C6	−178.81 (12)	C7A—N2A—C8A—C9A	27.2 (7)
C4—C5—C6—C1	1.3 (2)	N2A—C8A—C9A—C10A	−59.5 (8)
N1—C1—C6—C5	179.09 (13)	C7A—N3A—C10A—C9A	−58.3 (7)
C2—C1—C6—C5	−1.7 (2)	C8A—C9A—C10A—N3A	69.8 (8)
C8A—N2A—C7A—N3A	−11.2 (5)	C8B—C9B—C10B—N3B	−62.7 (7)
C8A—N2A—C7A—C4	175.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···Cl1i	0.90	2.47	3.3271 (16)	160
N2B—H2N···Cl1	0.90	2.27	3.1126 (12)	156
N3B—H3N···Cl1ii	0.90	2.42	3.250 (17)	153

N1	C1	1.372
N1	H1NB	1.008
N1	H1NA	1.008
N2	C7	1.332
N2	H2A	1.011
N2	C8	1.470
N3	C7	1.332
N3	C10	1.469
N3	H3	0.899
C1	C6	1.411
C1	C2	1.411
C2	C3	1.388
C2	H2	1.083
C3	C4	1.407
C3	H3	1.084
C4	C5	1.407
C4	C7	1.458
C5	C6	1.388
C5	H5	1.084
C6	H6	1.083
C8	C9	1.520
C8	H8A	1.089
C8	H8B	1.092
C9	C10	1.522
C9	H9A	1.089
C9	H9B	1.091
C10	H10A	1.087
C10	H10B	1.092

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯Cl1i	0.90	2.47	3.3271 (16)	160
N2B—H2N⋯Cl1	0.90	2.27	3.1126 (12)	156
N3B—H3N⋯Cl1ii	0.90	2.42	3.250 (17)	153

Symmetry codes: (i) ; (ii) .