Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025481/nc6042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025481/nc6042Isup2.hkl |
CCDC reference: 283960
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.027
- wR factor = 0.073
- Data-to-parameter ratio = 29.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 29.30 From the CIF: _reflns_number_total 2891 Count of symmetry unique reflns 1736 Completeness (_total/calc) 166.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1155 Fraction of Friedel pairs measured 0.665 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97.
C8H18N+·I− | Dx = 1.552 Mg m−3 |
Mr = 255.13 | Melting point: not measured K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 20726 reflections |
a = 7.6816 (8) Å | θ = 2.4–29.3° |
b = 11.8247 (15) Å | µ = 2.88 mm−1 |
c = 12.0196 (14) Å | T = 170 K |
V = 1091.8 (2) Å3 | Prism, white |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
F(000) = 504 |
Stoe IPDS-II diffractometer | 2891 independent reflections |
Radiation source: fine-focus sealed tube | 2796 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
φ scans | θmax = 29.3°, θmin = 2.4° |
Absorption correction: numerical [X-RED (Stoe & Cie, 2002) and X-SHAPE (Stoe & Cie, 2001)] | h = −10→10 |
Tmin = 0.468, Tmax = 0.697 | k = −15→15 |
14164 measured reflections | l = −16→16 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0366P)2 + 0.7962P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.073 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.77 e Å−3 |
2891 reflections | Δρmin = −0.73 e Å−3 |
98 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0164 (12) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1228 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (4) |
Experimental. A suitable single-crystal was carefully selected under a polarizing microscope and mounted in a glass capillary. The scattering intensities were collected with an imaging plate diffractometer (Stoe IPDS-II) equipped with a fine focus sealed tube X-ray source (Mo Kα, λ = 0.71073 Å) operating at 50 kV and 30 mA. Intensity data were collected at 173 K by φ scans in 360 frames (0 < φ < 180° exposure time of 6 min) in the 2Θ range 2.29 - °·Structure solution and refinement were carried out using the program SHELXL97 (Sheldrick, 1997). A numerical absorption correction (X-RED (Stoe & Cie, 2001) was applied after optimization of the crystal shape (X-SHAPE (Stoe & Cie, 2001)). The final difference maps were free of any chemically significant features. The refinement was based on F2 for ALL reflections. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
I | 0.18890 (2) | 0.189837 (14) | 0.243215 (17) | 0.03647 (9) | |
N | 0.3788 (4) | 0.5098 (2) | 0.0347 (3) | 0.0368 (6) | |
C1 | 0.2319 (5) | 0.5916 (4) | 0.0680 (4) | 0.0538 (11) | |
H1A | 0.1891 | 0.5743 | 0.1438 | 0.065* | |
H1B | 0.2735 | 0.6709 | 0.0663 | 0.065* | |
C2 | 0.0908 (5) | 0.5736 (4) | −0.0164 (3) | 0.0480 (8) | |
H2A | 0.1182 | 0.6110 | −0.0880 | 0.058* | 0.75 |
H2B | −0.0235 | 0.6004 | 0.0110 | 0.058* | 0.75 |
H2C | 0.0756 | 0.6425 | −0.0622 | 0.058* | 0.25 |
H2D | −0.0208 | 0.5569 | 0.0213 | 0.058* | 0.25 |
C3 | 0.0965 (7) | 0.4432 (5) | −0.0266 (5) | 0.0523 (12) | 0.75 |
H3A | 0.0408 | 0.4071 | 0.0386 | 0.063* | 0.75 |
H3B | 0.0360 | 0.4178 | −0.0949 | 0.063* | 0.75 |
C3' | 0.1453 (17) | 0.4722 (10) | −0.0913 (12) | 0.043 (3)* | 0.25 |
H3C | 0.0460 | 0.4200 | −0.1023 | 0.052* | 0.25 |
H3D | 0.1848 | 0.4993 | −0.1650 | 0.052* | 0.25 |
C4 | 0.2903 (5) | 0.4139 (3) | −0.0318 (4) | 0.0469 (9) | |
H4A | 0.3321 | 0.4125 | −0.1097 | 0.056* | 0.75 |
H4B | 0.3132 | 0.3394 | 0.0028 | 0.056* | 0.75 |
H4C | 0.3726 | 0.3790 | −0.0851 | 0.056* | 0.25 |
H4D | 0.2450 | 0.3545 | 0.0186 | 0.056* | 0.25 |
C5 | 0.5075 (5) | 0.5732 (3) | −0.0380 (4) | 0.0505 (10) | |
H5A | 0.4440 | 0.6183 | −0.0931 | 0.076* | |
H5B | 0.5831 | 0.5190 | −0.0764 | 0.076* | |
H5C | 0.5786 | 0.6233 | 0.0084 | 0.076* | |
C6 | 0.4676 (4) | 0.4625 (3) | 0.1376 (3) | 0.0370 (7) | |
H6A | 0.3816 | 0.4174 | 0.1800 | 0.044* | |
H6B | 0.5038 | 0.5266 | 0.1854 | 0.044* | |
C7 | 0.6269 (5) | 0.3885 (3) | 0.1150 (4) | 0.0436 (8) | |
H7A | 0.7214 | 0.4349 | 0.0826 | 0.052* | |
H7B | 0.5965 | 0.3284 | 0.0610 | 0.052* | |
C8 | 0.6889 (5) | 0.3348 (3) | 0.2248 (4) | 0.0494 (8) | |
H8A | 0.7088 | 0.3943 | 0.2800 | 0.074* | |
H8B | 0.7976 | 0.2934 | 0.2118 | 0.074* | |
H8C | 0.5998 | 0.2825 | 0.2523 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I | 0.03338 (11) | 0.03446 (12) | 0.04157 (14) | 0.00112 (6) | 0.00041 (8) | −0.00156 (8) |
N | 0.0326 (13) | 0.0326 (13) | 0.0453 (18) | 0.0024 (10) | −0.0051 (11) | −0.0076 (11) |
C1 | 0.0428 (19) | 0.061 (2) | 0.058 (3) | 0.0232 (17) | −0.0136 (17) | −0.0228 (19) |
C2 | 0.0377 (17) | 0.061 (2) | 0.045 (2) | 0.0080 (16) | −0.0030 (14) | 0.0014 (17) |
C3 | 0.042 (2) | 0.056 (3) | 0.059 (4) | −0.005 (2) | −0.011 (2) | 0.000 (3) |
C4 | 0.0437 (19) | 0.047 (2) | 0.050 (2) | −0.0005 (16) | −0.0050 (16) | −0.0177 (15) |
C5 | 0.053 (2) | 0.0413 (18) | 0.057 (3) | −0.0031 (16) | −0.0072 (16) | 0.0150 (17) |
C6 | 0.0316 (13) | 0.0339 (14) | 0.045 (2) | −0.0003 (11) | −0.0017 (13) | −0.0020 (12) |
C7 | 0.0350 (14) | 0.0449 (17) | 0.051 (2) | 0.0078 (13) | −0.0038 (15) | 0.0025 (15) |
C8 | 0.0419 (16) | 0.0491 (16) | 0.057 (2) | 0.0065 (13) | −0.0090 (17) | 0.0048 (15) |
N—C5 | 1.518 (5) | C3'—H3D | 0.9900 |
N—C6 | 1.520 (5) | C4—H4A | 0.9900 |
N—C1 | 1.539 (4) | C4—H4B | 0.9900 |
N—C4 | 1.545 (4) | C4—H4C | 0.9900 |
C1—C2 | 1.500 (5) | C4—H4D | 0.9900 |
C1—H1A | 0.9900 | C5—H5A | 0.9800 |
C1—H1B | 0.9900 | C5—H5B | 0.9800 |
C2—C3 | 1.547 (6) | C5—H5C | 0.9800 |
C2—C3' | 1.557 (11) | C6—C7 | 1.529 (4) |
C2—H2A | 0.9900 | C6—H6A | 0.9900 |
C2—H2B | 0.9900 | C6—H6B | 0.9900 |
C2—H2C | 0.9900 | C7—C8 | 1.540 (5) |
C2—H2D | 0.9900 | C7—H7A | 0.9900 |
C3—C4 | 1.530 (6) | C7—H7B | 0.9900 |
C3—H3A | 0.9900 | C8—H8A | 0.9800 |
C3—H3B | 0.9900 | C8—H8B | 0.9800 |
C3'—C4 | 1.493 (11) | C8—H8C | 0.9800 |
C3'—H3C | 0.9900 | ||
C5—N—C6 | 111.0 (3) | C3—C4—N | 103.9 (3) |
C5—N—C1 | 108.5 (3) | C3—C4—H4A | 111.0 |
C6—N—C1 | 110.4 (3) | N—C4—H4A | 111.0 |
C5—N—C4 | 110.6 (3) | C3'—C4—H4B | 138.2 |
C6—N—C4 | 110.4 (3) | C3—C4—H4B | 111.0 |
C1—N—C4 | 105.9 (3) | N—C4—H4B | 111.0 |
C2—C1—N | 105.3 (3) | H4A—C4—H4B | 109.0 |
C2—C1—H1A | 110.7 | C3'—C4—H4C | 111.0 |
N—C1—H1A | 110.7 | N—C4—H4C | 111.0 |
C2—C1—H1B | 110.7 | C3'—C4—H4D | 111.0 |
N—C1—H1B | 110.7 | N—C4—H4D | 111.0 |
H1A—C1—H1B | 108.8 | H4C—C4—H4D | 109.0 |
C1—C2—C3 | 100.1 (3) | N—C5—H5A | 109.5 |
C1—C2—C3' | 107.9 (5) | N—C5—H5B | 109.5 |
C1—C2—H2A | 111.8 | H5A—C5—H5B | 109.5 |
C3—C2—H2A | 111.8 | N—C5—H5C | 109.5 |
C1—C2—H2B | 111.8 | H5A—C5—H5C | 109.5 |
C3—C2—H2B | 111.8 | H5B—C5—H5C | 109.5 |
H2A—C2—H2B | 109.5 | N—C6—C7 | 115.1 (3) |
C1—C2—H2C | 110.1 | N—C6—H6A | 108.5 |
C3'—C2—H2C | 110.1 | C7—C6—H6A | 108.5 |
C1—C2—H2D | 110.1 | N—C6—H6B | 108.5 |
C3'—C2—H2D | 110.1 | C7—C6—H6B | 108.5 |
H2C—C2—H2D | 108.4 | H6A—C6—H6B | 107.5 |
C4—C3—C2 | 104.9 (4) | C6—C7—C8 | 109.3 (3) |
C4—C3—H3A | 110.8 | C6—C7—H7A | 109.8 |
C2—C3—H3A | 110.8 | C8—C7—H7A | 109.8 |
C4—C3—H3B | 110.8 | C6—C7—H7B | 109.8 |
C2—C3—H3B | 110.8 | C8—C7—H7B | 109.8 |
H3A—C3—H3B | 108.8 | H7A—C7—H7B | 108.3 |
C4—C3'—C2 | 106.2 (8) | C7—C8—H8A | 109.5 |
C4—C3'—H3C | 110.5 | C7—C8—H8B | 109.5 |
C2—C3'—H3C | 110.5 | H8A—C8—H8B | 109.5 |
C4—C3'—H3D | 110.5 | C7—C8—H8C | 109.5 |
C2—C3'—H3D | 110.5 | H8A—C8—H8C | 109.5 |
H3C—C3'—H3D | 108.7 | H8B—C8—H8C | 109.5 |
C3'—C4—N | 103.7 (5) |