N¹-(2,4-Dichloro­anilino)acetamidine

The title compound, C₈H₉Cl₂N₃, was synthesized by the reaction of ethyl acetimidate hydro­chloride and 2,4-dichloro­phenyl­hydrazine. Both intra­molecular N—H...Cl and inter­molecular N—H...N hydrogen-bond inter­actions are present, resulting in a one-dimensional supra­molecular chain structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.070
• wR factor = 0.214
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3     ...          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   1 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL.

N¹-(2,4-Dichloroanilino)acetamidine

Crystal data

C8H9Cl2N3	F(000) = 896
Mr = 218.08	Dx = 1.444 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 22.832 (5) Å	θ = 10–12°
b = 4.756 (1) Å	µ = 0.60 mm^−1
c = 20.515 (4) Å	T = 293 K
β = 115.74 (3)°	Block, colourless
V = 2006.7 (9) Å^3	0.40 × 0.30 × 0.10 mm
Z = 8

Data collection

Enraf-Nonius CAD-4 diffractometer	1178 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 26.0°, θmin = 2.0°
ω/2θ scans	h = 0→28
Absorption correction: ψ scan (North et al., 1968)	k = 0→5
Tmin = 0.795, Tmax = 0.942	l = −25→22
2013 measured reflections	3 standard reflections every 200 reflections
1966 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.070	H-atom parameters constrained
wR(F^2) = 0.214	w = 1/[σ^2(Fo^2) + (0.0946P)^2 + 3.9518P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.027
1966 reflections	Δρmax = 0.38 e Å^−3
120 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0105 (16)

Special details

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	0.1601 (2)	0.1845 (3)	0.5875 (2)	0.0546 (11)
C2	0.1960 (2)	0.3509 (5)	0.5631 (2)	0.0580 (11)
C3	0.2627 (2)	0.3669 (5)	0.5985 (2)	0.0728 (14)
H3A	0.2859	0.4806	0.5810	0.087*
C4	0.2944 (2)	0.2097 (3)	0.6607 (3)	0.0721 (14)
C5	0.2609 (3)	0.0446 (2)	0.6864 (3)	0.0761 (14)
H5A	0.2830	−0.0606	0.7282	0.091*
C6	0.1939 (2)	0.0326 (3)	0.6505 (2)	0.0688 (13)
H6A	0.1711	−0.0789	0.6689	0.083*
C7	0.0265 (2)	0.2692 (5)	0.6064 (3)	0.0650 (12)
C8	−0.0102 (2)	0.1534 (4)	0.6461 (3)	0.0793 (15)
H8A	0.0200	0.0747	0.6914	0.119*
H8B	−0.0396	0.0098	0.6173	0.119*
H8C	−0.0343	0.3019	0.6549	0.119*
Cl1	0.15608 (7)	0.5473 (3)	0.48471 (8)	0.0912 (6)
Cl2	0.37887 (7)	0.2259 (5)	0.70705 (9)	0.1213 (8)
N1	0.09229 (17)	0.1582 (8)	0.5468 (2)	0.0665 (10)
H1	0.0769	0.3248	0.5254	0.080*
N2	0.05714 (17)	0.0821 (7)	0.5850 (2)	0.0613 (10)
H2	0.0689	−0.0721	0.6087	0.074*
N3	0.0282 (2)	0.5174 (7)	0.5932 (3)	0.0906 (15)
H3	−0.0034	0.5979	0.5942	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.060 (2)	0.043 (2)	0.065 (3)	−0.005 (2)	0.031 (2)	−0.010 (2)
C2	0.072 (3)	0.046 (2)	0.064 (3)	0.002 (2)	0.036 (2)	−0.003 (2)
C3	0.075 (3)	0.070 (3)	0.085 (3)	−0.013 (3)	0.046 (3)	−0.008 (3)
C4	0.072 (3)	0.082 (3)	0.075 (3)	−0.013 (3)	0.029 (2)	−0.018 (3)
C5	0.074 (3)	0.082 (4)	0.063 (3)	0.006 (3)	0.022 (3)	−0.001 (3)
C6	0.078 (3)	0.058 (3)	0.071 (3)	−0.005 (2)	0.033 (3)	0.009 (2)
C7	0.071 (3)	0.046 (3)	0.077 (3)	0.002 (2)	0.031 (2)	0.005 (2)
C8	0.088 (3)	0.074 (3)	0.090 (4)	0.015 (3)	0.051 (3)	0.020 (3)
Cl1	0.0958 (10)	0.0936 (11)	0.0959 (11)	0.0115 (8)	0.0527 (8)	0.0353 (8)
Cl2	0.0651 (9)	0.175 (2)	0.1070 (12)	−0.0156 (10)	0.0213 (8)	−0.0170 (12)
N1	0.064 (2)	0.056 (2)	0.079 (2)	−0.0022 (19)	0.030 (2)	0.005 (2)
N2	0.065 (2)	0.0397 (19)	0.085 (3)	−0.0012 (17)	0.039 (2)	0.0069 (18)
N3	0.141 (4)	0.0387 (17)	0.151 (4)	0.010 (2)	0.099 (4)	0.013 (2)

Geometric parameters (Å, º)

C1—C2	1.382 (6)	C6—H6A	0.9300
C1—C6	1.386 (6)	C7—N3	1.215 (5)
C1—N1	1.409 (5)	C7—N2	1.319 (6)
C2—C3	1.375 (6)	C7—C8	1.504 (7)
C2—Cl1	1.737 (4)	C8—H8A	0.9600
C3—C4	1.381 (7)	C8—H8B	0.9600
C3—H3A	0.9300	C8—H8C	0.9600
C4—C5	1.354 (7)	N1—N2	1.391 (5)
C4—Cl2	1.742 (5)	N1—H1	0.9000
C5—C6	1.382 (6)	N2—H2	0.8552
C5—H5A	0.9300	N3—H3	0.8255
C2—C1—C6	117.3 (4)	C1—C6—H6A	119.5
C2—C1—N1	120.6 (4)	N3—C7—N2	120.6 (5)
C6—C1—N1	122.0 (4)	N3—C7—C8	123.8 (5)
C3—C2—C1	122.4 (4)	N2—C7—C8	115.7 (4)
C3—C2—Cl1	118.4 (4)	C7—C8—H8A	109.5
C1—C2—Cl1	119.2 (3)	C7—C8—H8B	109.5
C2—C3—C4	118.3 (4)	H8A—C8—H8B	109.5
C2—C3—H3A	120.9	C7—C8—H8C	109.5
C4—C3—H3A	120.9	H8A—C8—H8C	109.5
C5—C4—C3	121.0 (5)	H8B—C8—H8C	109.5
C5—C4—Cl2	119.4 (4)	N2—N1—C1	116.3 (3)
C3—C4—Cl2	119.5 (4)	N2—N1—H1	107.7
C4—C5—C6	119.9 (5)	C1—N1—H1	107.9
C4—C5—H5A	120.0	C7—N2—N1	122.0 (4)
C6—C5—H5A	120.0	C7—N2—H2	118.1
C5—C6—C1	121.0 (4)	N1—N2—H2	115.3
C5—C6—H6A	119.5	C7—N3—H3	109.4
C6—C1—C2—C3	0.6 (6)	Cl2—C4—C5—C6	179.3 (4)
N1—C1—C2—C3	−175.3 (4)	C4—C5—C6—C1	1.0 (8)
C6—C1—C2—Cl1	−179.6 (3)	C2—C1—C6—C5	−1.1 (7)
N1—C1—C2—Cl1	4.4 (5)	N1—C1—C6—C5	174.7 (4)
C1—C2—C3—C4	0.0 (7)	C2—C1—N1—N2	−156.3 (4)
Cl1—C2—C3—C4	−179.7 (4)	C6—C1—N1—N2	27.9 (6)
C2—C3—C4—C5	−0.2 (7)	N3—C7—N2—N1	−0.1 (8)
C2—C3—C4—Cl2	−179.8 (4)	C8—C7—N2—N1	179.1 (4)
C3—C4—C5—C6	−0.3 (8)	C1—N1—N2—C7	98.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.90	2.53	2.963 (4)	110
N2—H2···N3^i	0.86	2.13	2.788 (5)	134

Symmetry code: (i) x, y−1, z.