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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.
Supporting information
CCDC reference: 636623
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Plate, colourless |
Z = 4 | 0.44 × 0.26 × 0.12 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0297P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
38 constraints | Extinction coefficient: 0.0045 (5) |
Primary atom site location: structure-invariant direct methods | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···I1i | 0.89 | 2.81 | 3.562 (2) | 143 |
Symmetry code: (i) −x+2, −y+1, −z. |
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