4-Chloro­anilinium (4-chloro­phen­yl)guanidinium dichloride hemihydrate

Zhang, Y.; Liu, X.

doi:10.1107/S1600536810007774

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o790

doi:10.1107/S1600536810007774

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4-Chloroanilinium (4-chlorophenyl)guanidinium dichloride hemihydrate

Yanhua Zhang ^a ^* and Xiangyun Liu ^a

^aChemistry and Chemical Engineering Department, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China
^*Correspondence e-mail: dongthc2009@163.com

(Received 24 February 2010; accepted 1 March 2010; online 10 March 2010)

In the title hydrated molecular salt, C₆H₇ClN⁺·C₇H₉ClN₃⁺·2Cl⁻·0.5H₂O, the water O atom lies on a crystallographic twofold axis. In the crystal, intermolecular N—H⋯Cl and O—H⋯Cl hydrogen bonds form layers perpendicular to the ac plane in which both the water molecule and the chloride anion are involved in connecting the layers into a three-dimensional structure.

Related literature

For applications of guanidine-containing compounds, see: Yonehara & Otake (1966 ); Berlinck (1995 ); Gobbi & Frenking (1993 ). For related structures, see: Ploug-Sørenson & Andersen 1985 ; Kolev et al. (1997 ); Glidewell et al. (2005 ); Smith et al. (2005 ).

Experimental

Crystal data

C₆H₇ClN⁺·C₇H₉ClN₃⁺·2Cl⁻·0.5H₂O
M_r = 379.11
Monoclinic, C 2/c
a = 41.297 (8) Å
b = 4.2089 (8) Å
c = 23.695 (5) Å
β = 120.164 (2)°
V = 3560.8 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.67 mm⁻¹
T = 298 K
0.51 × 0.50 × 0.34 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.727, T_max = 0.805
8167 measured reflections
3078 independent reflections
2495 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.03
3078 reflections
211 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H14A⋯Cl1ⁱ	0.82 (2)	2.36 (2)	3.1797 (17)	177 (3)
N2—H2A⋯Cl2ⁱ	0.86	2.54	3.324 (2)	152
N3—H3A⋯Cl2ⁱ	0.86	2.48	3.281 (2)	155
N4—H4D⋯Cl2ⁱⁱ	0.82 (6)	2.39 (5)	3.185 (3)	164 (5)
N2—H2B⋯Cl2ⁱⁱⁱ	0.86	2.62	3.2457 (19)	131
N4—H4A⋯Cl1^iv	0.93 (6)	2.27 (6)	3.158 (3)	160 (5)
N1—H1A⋯Cl1^v	0.86	2.52	3.283 (2)	148
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y+1, z; (iii) x, y+2, z; (iv) x, y-1, z; (v) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007774/hg2652sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007774/hg2652Isup2.hkl

checkCIF report

Comment top

The guanidine-containing compounds have been employed as anti-microbials and fungicides on a considerable scale(Yonehara & Otake, 1966). The drugs containing guanidine framework are not only easy to transport(Berlinck, 1995), but also make the functions of absorption and osmosis more selective due to the good solubility of their various acid salts in aqueous solution(Gobbi & Frenking, 1993). We report here the cocrystal structure of title compound.

Title compound crystallizes with one 4-chloropenylguanidinium cation , one 4-chloroanilinium cation, two chloride anion and half water molecular in the asymmetric unit (Fig. 1). All bond lengths and angles are normal (Ploug-Sørenson & Andersen, 1985; Kolev et al., 1997; Glidewell et al., 2005; Smith et al., 2005). The forces between cations and anions consist of hydrogen bonding and ion-pairing. Intermolecular N—H···Cl and O—H···Cl hydrogen bonds form layers perpendicular to the ac plane in which both the water molecule and the chloride anion are involved in structure extension (Table 1).

Related literature top

For applications of guanidine-containing compounds, see: Yonehara & Otake (1966); Berlinck (1995); Gobbi & Frenking (1993). For related structures, see: Ploug-Sørenson & Andersen 1985; Kolev et al. (1997); Glidewell et al. (2005); Smith et al. (2005).

Experimental top

The 4-chlorophenylguanidine (0.01 mol) was added to a solution of 4-chlorobenzenamine (0.01 mol) in ethanol (20 ml) and stirred half hour at room temperature. The mixture was adjusted to pH 2-3 with concentrated hydrochloric acid, and the desired products then precipitated, which was collected by filtration. Single crystals suitable for X-ray measurements were obtained by recrystallization from methanol and water (v/v 1:1) at room temperature for one week.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level.

4-Chloroanilinium (4-chlorophenyl)guanidinium dichloride hemihydrate top

Crystal data top

C₆H₇ClN⁺·C₇H₉ClN₃⁺·2Cl⁻·0.5H₂O	F(000) = 1560
M_r = 379.11	D_x = 1.414 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2794 reflections
a = 41.297 (8) Å	θ = 2.6–24.3°
b = 4.2089 (8) Å	µ = 0.67 mm⁻¹
c = 23.695 (5) Å	T = 298 K
β = 120.164 (2)°	Block, colorless
V = 3560.8 (12) Å³	0.51 × 0.50 × 0.34 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −45→48
T_min = 0.727, T_max = 0.805	k = −5→4
8167 measured reflections	l = −27→28

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0657P)² + 0.9195P] where P = (F_o² + 2F_c²)/3
3078 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₆H₇ClN⁺·C₇H₉ClN₃⁺·2Cl⁻·0.5H₂O	V = 3560.8 (12) Å³
M_r = 379.11	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 41.297 (8) Å	µ = 0.67 mm⁻¹
b = 4.2089 (8) Å	T = 298 K
c = 23.695 (5) Å	0.51 × 0.50 × 0.34 mm
β = 120.164 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2495 reflections with I > 2σ(I)
T_min = 0.727, T_max = 0.805	R_int = 0.046
8167 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
3078 reflections	Δρ_min = −0.22 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	0.073762 (19)	0.49131 (14)	0.32708 (3)	0.0542 (2)
Cl2	0.062005 (17)	−0.51049 (14)	0.49527 (3)	0.0496 (2)
Cl3	0.20900 (2)	0.7771 (2)	0.72411 (4)	0.0787 (3)
Cl4	0.26245 (2)	0.1128 (3)	0.59514 (5)	0.0943 (3)
O1	0.0000	0.9261 (7)	0.7500	0.0535 (6)
H14A	−0.0188 (6)	0.815 (7)	0.7317 (14)	0.074 (10)*
N1	0.06411 (5)	1.1656 (6)	0.69506 (9)	0.0560 (6)
H1A	0.0648	1.1745	0.7319	0.067*
N2	0.02658 (6)	1.2676 (6)	0.58408 (9)	0.0583 (6)
H2A	0.0051	1.3206	0.5519	0.070*
H2B	0.0450	1.2324	0.5777	0.070*
N3	0.00277 (6)	1.2948 (6)	0.65192 (10)	0.0614 (6)
H3A	−0.0186	1.3477	0.6193	0.074*
H3B	0.0055	1.2777	0.6902	0.074*
N4	0.09760 (8)	−0.0049 (7)	0.43996 (17)	0.0644 (7)
C1	0.19749 (9)	−0.0652 (8)	0.48977 (15)	0.0711 (8)
H1B	0.2122	−0.1407	0.4731	0.085*
C2	0.15937 (8)	−0.0937 (7)	0.45442 (14)	0.0649 (7)
H2C	0.1480	−0.1909	0.4137	0.078*
C3	0.13796 (7)	0.0206 (5)	0.47893 (13)	0.0473 (6)
C4	0.15458 (8)	0.1594 (7)	0.53908 (13)	0.0604 (7)
H4C	0.1399	0.2353	0.5557	0.073*
C5	0.19272 (8)	0.1877 (7)	0.57510 (13)	0.0649 (7)
H5A	0.2040	0.2820	0.6161	0.078*
C6	0.21393 (8)	0.0766 (6)	0.55030 (13)	0.0569 (7)
C7	0.16604 (7)	0.8951 (6)	0.71382 (12)	0.0500 (6)
C8	0.16519 (8)	1.0740 (6)	0.76169 (13)	0.0572 (7)
H8A	0.1873	1.1340	0.7988	0.069*
C9	0.13103 (7)	1.1630 (7)	0.75378 (12)	0.0567 (7)
H9A	0.1301	1.2838	0.7858	0.068*
C10	0.09795 (6)	1.0742 (6)	0.69845 (11)	0.0429 (5)
C11	0.09949 (7)	0.8967 (6)	0.65113 (11)	0.0482 (6)
H11A	0.0775	0.8364	0.6137	0.058*
C12	0.13380 (7)	0.8084 (6)	0.65932 (13)	0.0522 (6)
H12A	0.1348	0.6886	0.6273	0.063*
C13	0.03129 (7)	1.2401 (6)	0.64323 (11)	0.0455 (6)
H4D	0.0856 (16)	0.130 (14)	0.446 (3)	0.17 (2)*
H4B	0.0890 (13)	−0.130 (12)	0.457 (2)	0.14 (2)*
H4A	0.0872 (15)	−0.110 (14)	0.400 (3)	0.18 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0552 (4)	0.0610 (4)	0.0393 (4)	−0.0094 (3)	0.0185 (3)	0.0031 (3)
Cl2	0.0461 (4)	0.0655 (4)	0.0406 (3)	0.0053 (3)	0.0243 (3)	0.0064 (3)
Cl3	0.0503 (4)	0.1045 (6)	0.0858 (6)	0.0173 (4)	0.0377 (4)	0.0099 (5)
Cl4	0.0518 (5)	0.1166 (7)	0.0872 (6)	−0.0050 (5)	0.0146 (4)	−0.0111 (5)
O1	0.0472 (16)	0.0582 (16)	0.0483 (15)	0.000	0.0191 (13)	0.000
N1	0.0399 (12)	0.0949 (17)	0.0320 (10)	0.0124 (12)	0.0172 (9)	0.0028 (11)
N2	0.0430 (12)	0.0954 (17)	0.0388 (11)	0.0095 (11)	0.0223 (10)	0.0160 (11)
N3	0.0434 (12)	0.1009 (18)	0.0432 (11)	0.0155 (12)	0.0241 (10)	0.0109 (12)
N4	0.0506 (15)	0.0518 (14)	0.081 (2)	−0.0028 (12)	0.0254 (15)	0.0001 (14)
C1	0.0595 (19)	0.093 (2)	0.0647 (18)	−0.0002 (17)	0.0344 (16)	−0.0173 (17)
C2	0.0610 (18)	0.0809 (19)	0.0507 (16)	−0.0073 (16)	0.0266 (14)	−0.0191 (15)
C3	0.0495 (15)	0.0382 (12)	0.0510 (14)	−0.0007 (10)	0.0230 (12)	0.0069 (11)
C4	0.0640 (18)	0.0716 (18)	0.0497 (15)	0.0065 (15)	0.0315 (14)	−0.0041 (14)
C5	0.0687 (19)	0.0749 (19)	0.0416 (14)	0.0009 (16)	0.0207 (14)	−0.0103 (13)
C6	0.0506 (15)	0.0593 (16)	0.0502 (15)	−0.0015 (13)	0.0174 (13)	0.0017 (13)
C7	0.0422 (14)	0.0550 (14)	0.0540 (15)	0.0063 (12)	0.0251 (12)	0.0086 (13)
C8	0.0439 (15)	0.0668 (17)	0.0461 (15)	0.0004 (13)	0.0116 (12)	−0.0033 (13)
C9	0.0479 (15)	0.0759 (18)	0.0364 (13)	0.0103 (14)	0.0137 (12)	−0.0065 (13)
C10	0.0394 (13)	0.0513 (13)	0.0351 (12)	0.0064 (11)	0.0167 (11)	0.0063 (10)
C11	0.0423 (14)	0.0536 (13)	0.0414 (13)	−0.0010 (12)	0.0155 (11)	−0.0049 (11)
C12	0.0545 (16)	0.0547 (15)	0.0514 (15)	0.0049 (12)	0.0295 (13)	−0.0057 (12)
C13	0.0404 (13)	0.0579 (14)	0.0382 (12)	0.0012 (11)	0.0197 (11)	0.0034 (11)

Geometric parameters (Å, º) top

Cl3—C7	1.738 (2)	C1—H1B	0.9300
Cl4—C6	1.740 (3)	C2—C3	1.366 (4)
O1—H14A	0.820 (17)	C2—H2C	0.9300
N1—C13	1.331 (3)	C3—C4	1.364 (4)
N1—C10	1.412 (3)	C4—C5	1.369 (4)
N1—H1A	0.8600	C4—H4C	0.9300
N2—C13	1.320 (3)	C5—C6	1.359 (4)
N2—H2A	0.8600	C5—H5A	0.9300
N2—H2B	0.8600	C7—C12	1.359 (4)
N3—C13	1.314 (3)	C7—C8	1.377 (4)
N3—H3A	0.8600	C8—C9	1.379 (4)
N3—H3B	0.8600	C8—H8A	0.9300
N4—C3	1.448 (4)	C9—C10	1.387 (3)
N4—H4D	0.82 (6)	C9—H9A	0.9300
N4—H4B	0.84 (5)	C10—C11	1.375 (3)
N4—H4A	0.93 (6)	C11—C12	1.381 (3)
C1—C2	1.367 (4)	C11—H11A	0.9300
C1—C6	1.377 (4)	C12—H12A	0.9300

C13—N1—C10	129.5 (2)	C6—C5—C4	119.4 (3)
C13—N1—H1A	115.2	C6—C5—H5A	120.3
C10—N1—H1A	115.2	C4—C5—H5A	120.3
C13—N2—H2A	120.0	C5—C6—C1	120.8 (3)
C13—N2—H2B	120.0	C5—C6—Cl4	120.0 (2)
H2A—N2—H2B	120.0	C1—C6—Cl4	119.2 (2)
C13—N3—H3A	120.0	C12—C7—C8	120.8 (2)
C13—N3—H3B	120.0	C12—C7—Cl3	120.0 (2)
H3A—N3—H3B	120.0	C8—C7—Cl3	119.2 (2)
C3—N4—H4D	116 (4)	C7—C8—C9	119.0 (2)
C3—N4—H4B	112 (3)	C7—C8—H8A	120.5
H4D—N4—H4B	85 (5)	C9—C8—H8A	120.5
C3—N4—H4A	119 (3)	C8—C9—C10	120.6 (2)
H4D—N4—H4A	120 (5)	C8—C9—H9A	119.7
H4B—N4—H4A	95 (4)	C10—C9—H9A	119.7
C2—C1—C6	119.3 (3)	C11—C10—C9	119.3 (2)
C2—C1—H1B	120.3	C11—C10—N1	123.5 (2)
C6—C1—H1B	120.3	C9—C10—N1	117.2 (2)
C3—C2—C1	120.0 (3)	C10—C11—C12	119.8 (2)
C3—C2—H2C	120.0	C10—C11—H11A	120.1
C1—C2—H2C	120.0	C12—C11—H11A	120.1
C4—C3—C2	120.1 (3)	C7—C12—C11	120.5 (2)
C4—C3—N4	120.8 (3)	C7—C12—H12A	119.7
C2—C3—N4	119.1 (3)	C11—C12—H12A	119.7
C3—C4—C5	120.4 (2)	N3—C13—N2	119.1 (2)
C3—C4—H4C	119.8	N3—C13—N1	118.3 (2)
C5—C4—H4C	119.8	N2—C13—N1	122.6 (2)

C6—C1—C2—C3	0.6 (5)	C7—C8—C9—C10	−0.1 (4)
C1—C2—C3—C4	−0.9 (4)	C8—C9—C10—C11	−0.3 (4)
C1—C2—C3—N4	178.4 (3)	C8—C9—C10—N1	177.9 (2)
C2—C3—C4—C5	0.5 (4)	C13—N1—C10—C11	−34.1 (4)
N4—C3—C4—C5	−178.8 (3)	C13—N1—C10—C9	147.8 (3)
C3—C4—C5—C6	0.1 (4)	C9—C10—C11—C12	0.2 (4)
C4—C5—C6—C1	−0.4 (4)	N1—C10—C11—C12	−177.8 (2)
C4—C5—C6—Cl4	179.6 (2)	C8—C7—C12—C11	−0.4 (4)
C2—C1—C6—C5	0.0 (5)	Cl3—C7—C12—C11	179.0 (2)
C2—C1—C6—Cl4	−180.0 (2)	C10—C11—C12—C7	0.1 (4)
C12—C7—C8—C9	0.4 (4)	C10—N1—C13—N3	174.8 (3)
Cl3—C7—C8—C9	−179.0 (2)	C10—N1—C13—N2	−6.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H14A···Cl1ⁱ	0.82 (2)	2.36 (2)	3.1797 (17)	177 (3)
N2—H2A···Cl2ⁱ	0.86	2.54	3.324 (2)	152
N3—H3A···Cl2ⁱ	0.86	2.48	3.281 (2)	155
N4—H4D···Cl2ⁱⁱ	0.82 (6)	2.39 (5)	3.185 (3)	164 (5)
N2—H2B···Cl2ⁱⁱⁱ	0.86	2.62	3.2457 (19)	131
N4—H4A···Cl1^iv	0.93 (6)	2.27 (6)	3.158 (3)	160 (5)
N1—H1A···Cl1^v	0.86	2.52	3.283 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₆H₇ClN⁺·C₇H₉ClN₃⁺·2Cl⁻·0.5H₂O
M_r	379.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	41.297 (8), 4.2089 (8), 23.695 (5)
β (°)	120.164 (2)
V (Å³)	3560.8 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.51 × 0.50 × 0.34

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.727, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	8167, 3078, 2495
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.122, 1.03
No. of reflections	3078
No. of parameters	211
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H14A···Cl1ⁱ	0.820 (17)	2.361 (17)	3.1797 (17)	177 (3)
N2—H2A···Cl2ⁱ	0.86	2.54	3.324 (2)	152.1
N3—H3A···Cl2ⁱ	0.86	2.48	3.281 (2)	154.8
N4—H4D···Cl2ⁱⁱ	0.82 (6)	2.39 (5)	3.185 (3)	164 (5)
N2—H2B···Cl2ⁱⁱⁱ	0.86	2.62	3.2457 (19)	130.7
N4—H4A···Cl1^iv	0.93 (6)	2.27 (6)	3.158 (3)	160 (5)
N1—H1A···Cl1^v	0.86	2.52	3.283 (2)	147.9

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

References

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Volume 66| Part 4| April 2010| Page o790

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