(E)-1-[(2-Chloro­phen­yl)methyl­eneamino]guanidinium chloride

The title compound, C₈H₁₀ClN₄⁺·Cl^-, was prepared by the condensation reaction of 2-chloro­benzaldehyde with amino­guanidine hydro­chloride. The guanidinium group is twisted by 21.88 (17)° from the 2-chloro­phenyl ring and the C=N group has E geometry. The chloride ions are involved in inter­molecular hydrogen bonds with the H atoms of the amino­guanidinium ion.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.141
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

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Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  C7     ..  C8      ..       3.15 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97, and local procedures.

(E)-1-[(2-Chlorophenyl)methyleneamino]guanidinium chloride

Crystal data

C8H10ClN4^+·Cl^−	F(000) = 480
Mr = 233.10	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3659 reflections
a = 16.5020 (14) Å	θ = 1.0–27.5°
b = 7.2234 (5) Å	µ = 0.61 mm^−1
c = 8.5816 (6) Å	T = 90 K
β = 100.768 (3)°	Plate, colourless
V = 1004.92 (13) Å^3	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2296 independent reflections
Radiation source: fine-focus sealed tube	1481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 1.3°
ω scans at fixed χ = 55°	h = −21→21
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.838, Tmax = 0.970	l = −10→11
7124 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 0.5156P] where P = (Fo^2 + 2Fc^2)/3
2296 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

Experimental. ¹H NMR (DMSO-d₆, p.p.m.): δ 7.39- 7.54 (m, 3H), 7.92 (s, 4H), 8.30 (dd, 1H), 8.55 (s, 1H), 12.34 (s, 1H). ¹³C NMR (DMSO-d₆, p.p.m.): δ 155.4, 142.6, 133.2, 131.9, 130.6, 129.9, 127.7, 127.5.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3815 (2)	0.1245 (4)	0.4082 (4)	0.0227 (7)
C2	0.4186 (2)	−0.0062 (4)	0.3287 (4)	0.0269 (8)
H2	0.4675	0.0226	0.2904	0.032*
C3	0.3836 (2)	−0.1807 (4)	0.3052 (4)	0.0266 (8)
H3	0.4080	−0.2717	0.2487	0.032*
C4	0.3130 (2)	−0.2228 (4)	0.3638 (4)	0.0258 (8)
H4	0.2892	−0.3425	0.3472	0.031*
C5	0.2774 (2)	−0.0920 (4)	0.4458 (4)	0.0241 (8)
H5	0.2296	−0.1231	0.4870	0.029*
C6	0.31063 (19)	0.0869 (4)	0.4695 (4)	0.0205 (7)
C7	0.26643 (19)	0.2291 (4)	0.5439 (4)	0.0203 (7)
H7	0.2780	0.3568	0.5327	0.024*
C8	0.11153 (19)	0.2625 (4)	0.7664 (4)	0.0193 (7)
N1	0.21228 (16)	0.1778 (3)	0.6236 (3)	0.0198 (6)
N2	0.16651 (15)	0.3145 (3)	0.6769 (3)	0.0215 (6)
H2A	0.1728	0.4316	0.6535	0.026*
N3	0.10098 (15)	0.0850 (3)	0.7932 (3)	0.0228 (6)
H3A	0.0665	0.0506	0.8546	0.027*
H3B	0.1284	0.0012	0.7496	0.027*
N4	0.07100 (16)	0.3910 (3)	0.8306 (3)	0.0233 (6)
H4A	0.0364	0.3587	0.8923	0.028*
H4B	0.0787	0.5088	0.8116	0.028*
Cl1	0.42507 (5)	0.34542 (11)	0.42910 (10)	0.0284 (3)
Cl2	−0.08855 (5)	0.21405 (10)	0.93388 (10)	0.0244 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0257 (18)	0.0167 (16)	0.0255 (19)	−0.0034 (13)	0.0045 (14)	−0.0012 (14)
C2	0.0264 (18)	0.0232 (17)	0.032 (2)	0.0021 (14)	0.0083 (15)	−0.0010 (16)
C3	0.0307 (19)	0.0183 (17)	0.031 (2)	0.0094 (14)	0.0072 (16)	−0.0017 (15)
C4	0.0314 (19)	0.0149 (16)	0.030 (2)	0.0021 (14)	0.0033 (15)	0.0009 (15)
C5	0.0266 (18)	0.0177 (17)	0.029 (2)	−0.0006 (14)	0.0075 (15)	0.0028 (15)
C6	0.0220 (17)	0.0174 (16)	0.0228 (18)	0.0044 (13)	0.0055 (14)	0.0032 (14)
C7	0.0251 (17)	0.0149 (15)	0.0203 (19)	−0.0005 (13)	0.0024 (14)	−0.0010 (14)
C8	0.0219 (16)	0.0142 (16)	0.0211 (18)	0.0012 (12)	0.0023 (14)	0.0030 (13)
N1	0.0225 (14)	0.0139 (13)	0.0229 (16)	0.0020 (11)	0.0040 (12)	−0.0016 (12)
N2	0.0237 (15)	0.0115 (13)	0.0306 (17)	0.0001 (11)	0.0088 (12)	0.0010 (12)
N3	0.0274 (15)	0.0178 (14)	0.0254 (16)	−0.0006 (11)	0.0107 (12)	−0.0025 (12)
N4	0.0304 (16)	0.0125 (13)	0.0292 (17)	−0.0006 (11)	0.0115 (13)	−0.0014 (12)
Cl1	0.0298 (5)	0.0190 (4)	0.0384 (6)	−0.0044 (3)	0.0120 (4)	−0.0015 (4)
Cl2	0.0331 (5)	0.0132 (4)	0.0290 (5)	−0.0001 (3)	0.0112 (4)	0.0013 (3)

Geometric parameters (Å, º)

C1—C2	1.374 (4)	C7—N1	1.278 (4)
C1—C6	1.396 (4)	C7—H7	0.9500
C1—Cl1	1.745 (3)	C8—N3	1.319 (4)
C2—C3	1.385 (4)	C8—N4	1.323 (4)
C2—H2	0.9500	C8—N2	1.347 (4)
C3—C4	1.386 (5)	N1—N2	1.373 (3)
C3—H3	0.9500	N2—H2A	0.8800
C4—C5	1.374 (4)	N3—H3A	0.8800
C4—H4	0.9500	N3—H3B	0.8800
C5—C6	1.404 (4)	N4—H4A	0.8800
C5—H5	0.9500	N4—H4B	0.8800
C6—C7	1.472 (4)
C2—C1—C6	122.4 (3)	C5—C6—C7	119.6 (3)
C2—C1—Cl1	117.8 (2)	N1—C7—C6	118.8 (3)
C6—C1—Cl1	119.8 (2)	N1—C7—H7	120.6
C1—C2—C3	119.1 (3)	C6—C7—H7	120.6
C1—C2—H2	120.5	N3—C8—N4	121.1 (3)
C3—C2—H2	120.5	N3—C8—N2	119.7 (3)
C2—C3—C4	120.2 (3)	N4—C8—N2	119.2 (3)
C2—C3—H3	119.9	C7—N1—N2	117.0 (2)
C4—C3—H3	119.9	C8—N2—N1	117.4 (2)
C5—C4—C3	120.3 (3)	C8—N2—H2A	121.3
C5—C4—H4	119.9	N1—N2—H2A	121.3
C3—C4—H4	119.9	C8—N3—H3A	120.0
C4—C5—C6	121.0 (3)	C8—N3—H3B	120.0
C4—C5—H5	119.5	H3A—N3—H3B	120.0
C6—C5—H5	119.5	C8—N4—H4A	120.0
C1—C6—C5	117.1 (3)	C8—N4—H4B	120.0
C1—C6—C7	123.1 (3)	H4A—N4—H4B	120.0
C6—C1—C2—C3	1.5 (5)	C4—C5—C6—C1	−0.8 (5)
Cl1—C1—C2—C3	−177.6 (3)	C4—C5—C6—C7	173.9 (3)
C1—C2—C3—C4	−1.1 (5)	C1—C6—C7—N1	−166.6 (3)
C2—C3—C4—C5	−0.1 (5)	C5—C6—C7—N1	19.0 (5)
C3—C4—C5—C6	1.1 (5)	C6—C7—N1—N2	−173.4 (3)
C2—C1—C6—C5	−0.5 (5)	N3—C8—N2—N1	−3.1 (4)
Cl1—C1—C6—C5	178.5 (2)	N4—C8—N2—N1	174.6 (3)
C2—C1—C6—C7	−175.0 (3)	C7—N1—N2—C8	−177.4 (3)
Cl1—C1—C6—C7	4.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2^i	0.88	2.50	3.230 (3)	140
N3—H3A···Cl2^ii	0.88	2.61	3.221 (3)	127
N3—H3B···Cl2^iii	0.88	2.61	3.297 (3)	135
N4—H4A···Cl2	0.88	2.40	3.197 (3)	152
N4—H4B···Cl2^i	0.88	2.61	3.305 (3)	137

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x, −y, −z+2; (iii) −x, y−1/2, −z+3/2.