4-Iodo-2,6-dimethyl­aniline

In the mol­ecule of the title compound, C₈H₁₀IN, the I, N and methyl C atoms lie in the benzene ring plane. In the crystal structure, inter­molecular N—H...N hydrogen bonds may be effective in stabilizing the structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         16
PLAT420_ALERT_2_C D-H Without Acceptor       N      -   H0B    ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.94
           From the CIF: _reflns_number_total               1036
           Count of symmetry unique reflns         1037
           Completeness (_total/calc)             99.90%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, (I), contains amino and halogen groups, in which they can react with different groups to prepare various functional organic compounds. It is a kind of aromatic organic intermediate that can be used for many fields such as aromatic conductive polymers, organometallic chemistry etc. (Zielinska & Skulski, 2005). We herein report its crystal structure.

In the molecule of (I), (Fig. 1), the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987), which can be compared with the corresponding values in 2-iodo-N-(3-nitrobenzyl)aniline (Glidewell et al., 2002). The atoms I, N and methyl carbons lie in the benzene ring plane.

In the crystal structure, intermolecular N—H···N hydrogen bonds (Table 2) may be effective in the stabilization of the structure, the molecules are stacked along the a axis (Fig. 2).

Related literature

For bond-length data, see: Allen et al. (1987). For related literature, see: Zielinska & Skulski (2005); Glidewell et al. (2002).

S2. Experimental

The title compound, (I) was prepared by the literature method (Zielinska & Skulski, 2005). The crystals were obtained by dissolving (I) (0.5 g) in hexane (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.

S3. Refinement

H atoms were positioned geometrically, with N—H = 0.86 Å (for NH₂) and C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

4-iodo-2,6-dimethylaniline

Crystal data

C8H10IN	Dx = 1.846 Mg m^−3
Mr = 247.07	Melting point: 324 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 4.841 (1) Å	θ = 10–13°
b = 11.389 (2) Å	µ = 3.53 mm^−1
c = 16.128 (3) Å	T = 298 K
V = 889.2 (3) Å^3	Needle, white
Z = 4	0.40 × 0.20 × 0.20 mm
F(000) = 472

Data collection

Enraf-Nonius CAD-4 diffractometer	867 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.9°, θmin = 2.2°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.306, Tmax = 0.496	l = 0→19
1036 measured reflections	3 standard reflections every 120 min
1036 independent reflections	intensity decay: 1%

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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.08P)^2 + 4P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1036 reflections	Δρmax = 0.62 e Å^−3
93 parameters	Δρmin = −0.89 e Å^−3
0 restraints	Absolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.16 (13)

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
I	0.9368 (2)	0.13850 (9)	0.90849 (5)	0.0746 (4)
N	1.380 (2)	0.1794 (9)	0.5450 (6)	0.056 (3)
H0A	1.4925	0.2344	0.5312	0.067*
H0B	1.3201	0.1311	0.5081	0.067*
C1	0.982 (3)	−0.0018 (11)	0.5800 (8)	0.069 (4)
H1A	0.9108	0.0430	0.5344	0.103*
H1B	0.8381	−0.0499	0.6027	0.103*
H1C	1.1303	−0.0510	0.5609	0.103*
C2	1.602 (3)	0.3380 (10)	0.6666 (8)	0.054 (3)
H2A	1.5346	0.3866	0.6224	0.081*
H2B	1.7700	0.3002	0.6496	0.081*
H2C	1.6372	0.3855	0.7146	0.081*
C3	1.385 (2)	0.2443 (8)	0.6879 (7)	0.041 (2)
C4	1.286 (3)	0.2360 (10)	0.7675 (7)	0.050 (3)
H4A	1.3503	0.2874	0.8079	0.060*
C5	1.095 (3)	0.1533 (9)	0.7877 (6)	0.045 (2)
C6	0.994 (2)	0.0768 (11)	0.7285 (7)	0.056 (3)
H6A	0.8615	0.0215	0.7429	0.067*
C7	1.092 (3)	0.0824 (9)	0.6476 (6)	0.046 (3)
C8	1.293 (2)	0.1686 (9)	0.6277 (6)	0.040 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.0877 (7)	0.0859 (6)	0.0504 (5)	−0.0028 (6)	0.0114 (5)	0.0090 (4)
N	0.060 (7)	0.058 (5)	0.050 (5)	0.000 (5)	0.001 (5)	0.012 (4)
C1	0.085 (11)	0.051 (6)	0.070 (8)	−0.018 (7)	0.008 (8)	−0.007 (6)
C2	0.047 (7)	0.048 (6)	0.066 (7)	−0.017 (6)	0.000 (6)	−0.007 (5)
C3	0.034 (6)	0.039 (5)	0.050 (5)	0.007 (5)	−0.002 (5)	−0.004 (4)
C4	0.051 (7)	0.045 (5)	0.055 (6)	−0.006 (6)	−0.002 (6)	0.004 (5)
C5	0.052 (7)	0.041 (5)	0.043 (5)	0.003 (6)	0.001 (5)	0.002 (4)
C6	0.049 (8)	0.057 (6)	0.061 (7)	−0.005 (6)	0.004 (6)	0.013 (6)
C7	0.044 (6)	0.043 (5)	0.051 (6)	0.012 (6)	−0.019 (6)	−0.002 (5)
C8	0.028 (5)	0.047 (6)	0.045 (5)	0.002 (5)	0.001 (4)	−0.004 (4)

Geometric parameters (Å, º)

I—C5	2.101 (10)	N—H0A	0.8600
C1—C7	1.545 (16)	N—H0B	0.8600
C1—H1A	0.9600	C8—C3	1.372 (14)
C1—H1B	0.9600	C8—C7	1.421 (16)
C1—H1C	0.9600	C7—C6	1.389 (16)
C2—C3	1.537 (15)	C6—C5	1.380 (17)
C2—H2A	0.9600	C6—H6A	0.9300
C2—H2B	0.9600	C5—C4	1.359 (16)
C2—H2C	0.9600	C4—C3	1.373 (16)
N—C8	1.404 (14)	C4—H4A	0.9300
C7—C1—H1A	109.5	N—C8—C7	118.7 (9)
C7—C1—H1B	109.5	C6—C7—C8	118.4 (10)
H1A—C1—H1B	109.5	C6—C7—C1	121.3 (11)
C7—C1—H1C	109.5	C8—C7—C1	120.3 (10)
H1A—C1—H1C	109.5	C5—C6—C7	120.1 (11)
H1B—C1—H1C	109.5	C5—C6—H6A	120.0
C3—C2—H2A	109.5	C7—C6—H6A	120.0
C3—C2—H2B	109.5	C4—C5—C6	120.8 (10)
H2A—C2—H2B	109.5	C4—C5—I	121.7 (8)
C3—C2—H2C	109.5	C6—C5—I	117.5 (8)
H2A—C2—H2C	109.5	C5—C4—C3	120.5 (11)
H2B—C2—H2C	109.5	C5—C4—H4A	119.7
C8—N—H0A	120.0	C3—C4—H4A	119.7
C8—N—H0B	120.0	C8—C3—C4	120.4 (10)
H0A—N—H0B	120.0	C8—C3—C2	120.0 (10)
C3—C8—N	121.4 (10)	C4—C3—C2	119.6 (10)
C3—C8—C7	119.8 (10)
C3—C8—C7—C6	−0.6 (16)	C6—C5—C4—C3	−0.7 (18)
N—C8—C7—C6	−176.2 (10)	I—C5—C4—C3	−179.5 (9)
C3—C8—C7—C1	178.8 (11)	N—C8—C3—C4	176.5 (11)
N—C8—C7—C1	3.2 (16)	C7—C8—C3—C4	1.1 (16)
C8—C7—C6—C5	−0.5 (17)	N—C8—C3—C2	−4.4 (16)
C1—C7—C6—C5	−179.9 (11)	C7—C8—C3—C2	−179.8 (10)
C7—C6—C5—C4	1.2 (18)	C5—C4—C3—C8	−0.5 (17)
C7—C6—C5—I	−180.0 (8)	C5—C4—C3—C2	−179.5 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···N^i	0.86	2.45	3.248 (12)	155

Symmetry code: (i) x+1/2, −y+1/2, −z+1.