2,4,6-Trimethyl­anilinium iodide

In the crystal structure of 2,4,6-trimethyl­anilinium iodide, C₉H₁₁NH₃⁺·I⁻, both ions are situated on mirror planes. The trimethyl­anilinium ions stack head-to-tail with no π–π inter­actions. The ammonium cations and I⁻ anions inter­act via hydrogen bonds, forming ladder-like columns parallel to the b axis. The structure is compared to the related anilinium iodide.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.060
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         N1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7

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
   4 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
   0 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998\); cell refinement: SAINT-Plus (Bruker, 1999\); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997\); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997\); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997\) and DIAMOND (Brandenburg, 1999\); software used to prepare material for publication: WinGX (Farrugia, 1999\) and PLATON (Spek, 2003\).

2,4,6-trimethylanilinium iodide

Crystal data

C9H14N^+·I^−	F(000) = 512
Mr = 263.11	Dx = 1.646 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 842 reflections
a = 17.814 (2) Å	θ = 2.6–28.2°
b = 6.8175 (8) Å	µ = 2.96 mm^−1
c = 8.7449 (11) Å	T = 293 K
V = 1062.0 (2) Å^3	Plate, colourless
Z = 4	0.44 × 0.26 × 0.12 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	1426 independent reflections
Radiation source: fine-focus sealed tube	1243 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: integration (XPREP; Bruker, 1999\)	h = −23→23
Tmin = 0.333, Tmax = 0.708	k = −9→6
7017 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.0297P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
1426 reflections	Δρmax = 0.44 e Å^−3
68 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
38 constraints	Extinction coefficient: 0.0045 (5)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.83249 (14)	0.25	0.1357 (3)	0.0367 (5)
C2	0.80644 (17)	0.25	0.2869 (3)	0.0425 (6)
C3	0.72880 (19)	0.25	0.3065 (3)	0.0495 (7)
H3	0.7095	0.25	0.4054	0.059*
C4	0.67940 (18)	0.25	0.1847 (4)	0.0505 (7)
C5	0.70875 (16)	0.25	0.0381 (3)	0.0463 (7)
H5	0.6759	0.25	−0.0446	0.056*
C6	0.78589 (15)	0.25	0.0101 (3)	0.0413 (6)
C7	0.8139 (2)	0.25	−0.1526 (3)	0.0554 (8)
H7A	0.7719	0.25	−0.2214	0.083*
H7B	0.8438	0.365	−0.17	0.083*
C8	0.85995 (18)	0.25	0.4209 (3)	0.0558 (8)
H8A	0.8319	0.25	0.5146	0.084*
H8B	0.891	0.365	0.4167	0.084*
C9	0.5960 (2)	0.25	0.2114 (5)	0.0687 (11)
H9A	0.5861	0.25	0.3193	0.103*
H9B	0.5743	0.365	0.166	0.103*
N1	0.91463 (12)	0.25	0.1142 (3)	0.0432 (5)
H1A	0.9251	0.25	0.0147	0.065*
H1B	0.9341	0.3566	0.1575	0.065*
I1	0.955428 (12)	0.75	0.19540 (2)	0.05589 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0347 (13)	0.0286 (12)	0.0469 (14)	0	0.0065 (11)	0
C2	0.0438 (15)	0.0387 (16)	0.0450 (15)	0	0.0066 (11)	0
C3	0.0432 (16)	0.0520 (19)	0.0535 (17)	0	0.0157 (12)	0
C4	0.0374 (15)	0.0390 (16)	0.075 (2)	0	0.0090 (13)	0
C5	0.0415 (15)	0.0426 (16)	0.0548 (16)	0	−0.0031 (12)	0
C6	0.0446 (15)	0.0324 (13)	0.0469 (14)	0	0.0041 (11)	0
C7	0.0647 (19)	0.0537 (19)	0.0477 (16)	0	0.0050 (14)	0
C8	0.0577 (19)	0.066 (2)	0.0434 (16)	0	−0.0014 (13)	0
C9	0.0394 (17)	0.071 (3)	0.095 (3)	0	0.0138 (16)	0
N1	0.0368 (12)	0.0408 (13)	0.0522 (13)	0	0.0070 (10)	0
I1	0.05940 (17)	0.03821 (14)	0.07006 (18)	0	0.02705 (9)	0

Geometric parameters (Å, º)

C1—C6	1.376 (4)	C5—H5	0.93
C1—C2	1.401 (4)	C6—C7	1.508 (4)
C1—N1	1.475 (3)	C7—H7A	0.96
C2—C3	1.394 (4)	C7—H7B	0.96
C2—C8	1.511 (4)	C8—H8A	0.96
C3—C4	1.382 (5)	C8—H8B	0.96
C3—H3	0.93	C9—H9A	0.96
C4—C5	1.385 (4)	C9—H9B	0.96
C4—C9	1.504 (5)	N1—H1A	0.89
C5—C6	1.396 (4)	N1—H1B	0.89
C6—C1—C2	123.6 (2)	C1—C6—C5	117.0 (3)
C6—C1—N1	119.8 (2)	C1—C6—C7	123.6 (3)
C2—C1—N1	116.7 (3)	C5—C6—C7	119.4 (3)
C3—C2—C1	116.4 (3)	C6—C7—H7A	109.5
C3—C2—C8	122.0 (3)	C6—C7—H7B	109.5
C1—C2—C8	121.5 (3)	H7A—C7—H7B	109.5
C4—C3—C2	122.5 (3)	C2—C8—H8A	109.5
C4—C3—H3	118.8	C2—C8—H8B	109.5
C2—C3—H3	118.8	H8A—C8—H8B	109.5
C3—C4—C5	118.3 (3)	C4—C9—H9A	109.5
C3—C4—C9	120.6 (3)	C4—C9—H9B	109.5
C5—C4—C9	121.1 (3)	H9A—C9—H9B	109.5
C4—C5—C6	122.3 (3)	C1—N1—H1A	109.5
C4—C5—H5	118.9	C1—N1—H1B	109.5
C6—C5—H5	118.9	H1A—N1—H1B	109.5
C6—C1—C2—C3	0	C3—C4—C5—C6	0
N1—C1—C2—C3	180	C9—C4—C5—C6	180
C6—C1—C2—C8	180	C2—C1—C6—C5	0
N1—C1—C2—C8	0	N1—C1—C6—C5	180
C1—C2—C3—C4	0	C2—C1—C6—C7	180
C8—C2—C3—C4	180	N1—C1—C6—C7	0
C2—C3—C4—C5	0	C4—C5—C6—C1	0
C2—C3—C4—C9	180	C4—C5—C6—C7	180

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···I1	0.89	2.73	3.5570 (8)	155
N1—H1A···I1^i	0.89	2.81	3.562 (2)	143

Symmetry code: (i) −x+2, −y+1, −z.