Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020639/cm6022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020639/cm6022Isup2.hkl |
CCDC reference: 202334
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.007 Å
- R factor = 0.036
- wR factor = 0.141
- Data-to-parameter ratio = 14.7
checkCIF results
No syntax errors found
Alert Level B:
PLAT_112 Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem. S
Author response: The ADDSYM procedure detects this pseudo symmetry element when the distance criterion for coinciding atoms is not fulfilled. The default value for this parameter is 0.45 Angstrom. In this crystal structure, only four pairs of atoms (F11 - F24; C313 - C122; C124 - C314; F13 - F12) and the iodine atoms are related by a non-crystallographic translation of coordinates (0.511, 0.754, 0.008), which make them lie less than 0.45 Angstrom far apart. Noteworthy, only the iodine atoms are clearly close to each other after this translation (approximately 0.15 Angstrom), the rest of atoms being more than 0.43 Angstrom far apart. When the default value of the distance criterion is reset to 0.43 Angstrom, the automatic procedure ADDSYM does not detect this pseudo symmetry. Furthermore, the PLATON/CHECKCIF procedures ADDSYM EXACT and NEWSYM indicate that no obvious spacegroup change is needed. As indicated in the main text, the iodine atoms in the crystal structure seem to be defining a higher symmetry than the actual one which, on the other hand, is not supported by the remainder unit cell contents. |
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.416 0.673 Tmin and Tmax expected: 0.350 0.673 RR = 1.189 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
Crystals of (I) were grown at ambient temperature by slow diffusion of diethyl ether into a solution of the compound in dichloromethane. These crystals appeared to be photosensible and deteriorate after a few days in the presence of visible light. Care was therefore taken during the whole process to reduce at minimum the exposure of the crystals to direct ambient light.
The correct assignement of the space group was done after a careful analysis of the experimental data. The reflection conditions corresponding to space group P21/c were clearly fulfilled. In addition, some other doubtful systematic absences seemed to suggest that a possible centring was present in the crystal structure. However, the intensity associated to these reflections, although not very strong, could be considered as observed. All possible space groups compatible with these doubtful systematic absences were checked, but the crystal structure could only be solved when all of these absences were discarded and the correct space group, P21/c, was chosen. All H atoms were positioned geometrically and allowed to ride on their respective parent atoms, with Uiso(H) values equal to 1.2Ueq(C).
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97.
C10H10IN2+·BF4− | F(000) = 1424 |
Mr = 371.91 | Dx = 1.911 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 5040 reflections |
a = 12.1840 (4) Å | θ = 2.0–70.0° |
b = 15.7830 (4) Å | µ = 19.80 mm−1 |
c = 14.8550 (3) Å | T = 120 K |
β = 115.1760 (16)° | Plate, colourless |
V = 2585.25 (12) Å3 | 0.10 × 0.05 × 0.02 mm |
Z = 8 |
Nonius KappaCCD diffractometer | 4821 independent reflections |
Radiation source: fine-focus sealed tube | 3369 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.029 |
Detector resolution: 9 pixels mm-1 | θmax = 69.8°, θmin = 4.3° |
ϕ and ω scans | h = −14→13 |
Absorption correction: empirical (using intensity measurements) (XABS2 (Parkin et al., 1995) | k = 0→19 |
Tmin = 0.416, Tmax = 0.673 | l = 0→18 |
9437 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3 |
4821 reflections | (Δ/σ)max = 0.001 |
328 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −1.35 e Å−3 |
C10H10IN2+·BF4− | V = 2585.25 (12) Å3 |
Mr = 371.91 | Z = 8 |
Monoclinic, P21/c | Cu Kα radiation |
a = 12.1840 (4) Å | µ = 19.80 mm−1 |
b = 15.7830 (4) Å | T = 120 K |
c = 14.8550 (3) Å | 0.10 × 0.05 × 0.02 mm |
β = 115.1760 (16)° |
Nonius KappaCCD diffractometer | 4821 independent reflections |
Absorption correction: empirical (using intensity measurements) (XABS2 (Parkin et al., 1995) | 3369 reflections with I > 2σ(I) |
Tmin = 0.416, Tmax = 0.673 | Rint = 0.029 |
9437 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.97 e Å−3 |
4821 reflections | Δρmin = −1.35 e Å−3 |
328 parameters |
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 | ||
I1 | 0.48947 (3) | 0.746188 (15) | 0.99242 (2) | 0.02600 (16) | |
N11 | 0.3524 (3) | 0.8515 (2) | 0.9311 (2) | 0.0297 (8) | |
C111 | 0.2506 (4) | 0.8382 (3) | 0.8464 (3) | 0.0350 (10) | |
H111 | 0.2378 | 0.7844 | 0.8150 | 0.042* | |
C112 | 0.1662 (4) | 0.9005 (3) | 0.8052 (3) | 0.0342 (10) | |
H112 | 0.0955 | 0.8905 | 0.7455 | 0.041* | |
C113 | 0.1858 (4) | 0.9788 (3) | 0.8522 (4) | 0.0372 (12) | |
H113 | 0.1287 | 1.0233 | 0.8247 | 0.045* | |
C114 | 0.2879 (5) | 0.9913 (3) | 0.9385 (4) | 0.0372 (14) | |
H114 | 0.3020 | 1.0443 | 0.9718 | 0.045* | |
C115 | 0.3694 (4) | 0.9267 (2) | 0.9763 (3) | 0.0323 (10) | |
H115 | 0.4400 | 0.9355 | 1.0363 | 0.039* | |
N12 | 0.6210 (3) | 0.6369 (2) | 1.0501 (2) | 0.0282 (8) | |
C121 | 0.7132 (4) | 0.6395 (3) | 1.1410 (3) | 0.0366 (11) | |
H121 | 0.7255 | 0.6888 | 1.1807 | 0.044* | |
C122 | 0.7903 (4) | 0.5713 (3) | 1.1773 (3) | 0.0406 (11) | |
H122 | 0.8554 | 0.5739 | 1.2418 | 0.049* | |
C123 | 0.7733 (5) | 0.5002 (3) | 1.1207 (4) | 0.0393 (14) | |
H123 | 0.8256 | 0.4527 | 1.1453 | 0.047* | |
C124 | 0.6780 (5) | 0.4986 (3) | 1.0263 (5) | 0.0427 (14) | |
H124 | 0.6646 | 0.4499 | 0.9853 | 0.051* | |
C125 | 0.6033 (4) | 0.5679 (3) | 0.9929 (3) | 0.0338 (10) | |
H125 | 0.5382 | 0.5669 | 0.9283 | 0.041* | |
I2 | 0.0000 | 1.0000 | 0.0000 | 0.02495 (17) | |
N21 | 0.1203 (3) | 0.8844 (2) | 0.0503 (2) | 0.0284 (8) | |
C211 | 0.0888 (4) | 0.8147 (2) | −0.0061 (3) | 0.0344 (10) | |
H211 | 0.0168 | 0.8149 | −0.0664 | 0.041* | |
C212 | 0.1590 (5) | 0.7426 (3) | 0.0215 (4) | 0.0418 (13) | |
H212 | 0.1364 | 0.6936 | −0.0195 | 0.050* | |
C213 | 0.2638 (6) | 0.7425 (3) | 0.1109 (5) | 0.0400 (14) | |
H213 | 0.3130 | 0.6933 | 0.1324 | 0.048* | |
C214 | 0.2941 (4) | 0.8154 (3) | 0.1671 (4) | 0.0408 (11) | |
H214 | 0.3655 | 0.8174 | 0.2278 | 0.049* | |
C215 | 0.2203 (4) | 0.8852 (3) | 0.1349 (3) | 0.0323 (10) | |
H215 | 0.2413 | 0.9352 | 0.1741 | 0.039* | |
I3 | 1.0000 | 0.5000 | 1.0000 | 0.02676 (17) | |
N31 | 0.8531 (3) | 0.5978 (2) | 0.9268 (2) | 0.0271 (8) | |
C311 | 0.7616 (4) | 0.5817 (2) | 0.8372 (3) | 0.0330 (10) | |
H311 | 0.7583 | 0.5282 | 0.8069 | 0.040* | |
C312 | 0.6733 (4) | 0.6406 (3) | 0.7886 (3) | 0.0359 (10) | |
H312 | 0.6096 | 0.6281 | 0.7254 | 0.043* | |
C313 | 0.6784 (4) | 0.7187 (3) | 0.8330 (3) | 0.0359 (11) | |
H313 | 0.6189 | 0.7608 | 0.8007 | 0.043* | |
C314 | 0.7720 (5) | 0.7339 (3) | 0.9257 (4) | 0.0316 (11) | |
H314 | 0.7767 | 0.7865 | 0.9580 | 0.038* | |
C315 | 0.8578 (4) | 0.6730 (2) | 0.9704 (3) | 0.0288 (9) | |
H315 | 0.9220 | 0.6842 | 1.0338 | 0.035* | |
B1 | 0.4621 (5) | 0.0538 (3) | 0.2261 (4) | 0.0306 (11) | |
F11 | 0.5145 (3) | 0.11642 (19) | 0.2961 (2) | 0.0702 (9) | |
F12 | 0.4461 (3) | −0.01702 (19) | 0.2743 (2) | 0.0544 (8) | |
F13 | 0.5358 (3) | 0.0324 (2) | 0.1810 (2) | 0.0578 (8) | |
F14 | 0.3494 (2) | 0.08063 (15) | 0.15621 (19) | 0.0484 (7) | |
B2 | 0.9565 (4) | 0.7012 (3) | 0.7202 (4) | 0.0319 (11) | |
F21 | 0.9342 (3) | 0.75717 (19) | 0.7808 (2) | 0.0602 (10) | |
F22 | 1.0299 (3) | 0.73925 (19) | 0.6826 (2) | 0.0564 (9) | |
F23 | 0.8474 (2) | 0.67767 (15) | 0.64236 (19) | 0.0494 (7) | |
F24 | 1.0139 (3) | 0.6311 (2) | 0.7756 (3) | 0.0896 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0263 (2) | 0.0230 (2) | 0.0318 (3) | 0.00292 (10) | 0.01534 (18) | 0.00357 (10) |
N11 | 0.030 (2) | 0.0277 (18) | 0.031 (2) | 0.0015 (15) | 0.0133 (17) | 0.0033 (15) |
C111 | 0.039 (3) | 0.025 (2) | 0.046 (3) | 0.0004 (18) | 0.022 (2) | 0.0035 (18) |
C112 | 0.034 (2) | 0.033 (2) | 0.036 (2) | 0.0024 (19) | 0.015 (2) | 0.0082 (19) |
C113 | 0.047 (3) | 0.028 (2) | 0.048 (3) | 0.014 (2) | 0.032 (3) | 0.014 (2) |
C114 | 0.049 (4) | 0.028 (2) | 0.044 (3) | −0.001 (2) | 0.029 (3) | −0.003 (2) |
C115 | 0.037 (3) | 0.027 (2) | 0.035 (2) | −0.0025 (18) | 0.017 (2) | −0.0034 (18) |
N12 | 0.0255 (19) | 0.0309 (18) | 0.031 (2) | 0.0033 (14) | 0.0153 (17) | 0.0053 (15) |
C121 | 0.030 (3) | 0.043 (3) | 0.035 (3) | 0.0004 (19) | 0.012 (2) | 0.004 (2) |
C122 | 0.028 (3) | 0.056 (3) | 0.035 (3) | 0.008 (2) | 0.011 (2) | 0.012 (2) |
C123 | 0.036 (3) | 0.041 (3) | 0.046 (4) | 0.014 (2) | 0.022 (3) | 0.016 (2) |
C124 | 0.048 (3) | 0.026 (3) | 0.066 (4) | 0.0003 (19) | 0.036 (3) | 0.001 (2) |
C125 | 0.041 (3) | 0.030 (2) | 0.037 (2) | 0.0005 (19) | 0.024 (2) | −0.0009 (19) |
I2 | 0.0243 (3) | 0.0219 (3) | 0.0307 (3) | 0.00227 (13) | 0.0138 (2) | 0.00343 (13) |
N21 | 0.0292 (19) | 0.0260 (18) | 0.0314 (19) | 0.0035 (14) | 0.0143 (17) | 0.0025 (14) |
C211 | 0.042 (3) | 0.030 (2) | 0.040 (3) | 0.0010 (19) | 0.025 (2) | 0.0023 (19) |
C212 | 0.054 (4) | 0.024 (2) | 0.062 (4) | 0.000 (2) | 0.039 (3) | 0.001 (2) |
C213 | 0.044 (4) | 0.036 (3) | 0.049 (4) | 0.016 (2) | 0.029 (3) | 0.018 (2) |
C214 | 0.027 (2) | 0.050 (3) | 0.044 (3) | 0.009 (2) | 0.014 (2) | 0.014 (2) |
C215 | 0.028 (2) | 0.034 (2) | 0.033 (2) | 0.0008 (18) | 0.011 (2) | 0.0033 (19) |
I3 | 0.0303 (3) | 0.0201 (3) | 0.0354 (3) | 0.00309 (13) | 0.0194 (2) | 0.00236 (14) |
N31 | 0.0272 (19) | 0.0247 (17) | 0.0325 (19) | 0.0008 (14) | 0.0156 (16) | 0.0014 (14) |
C311 | 0.043 (3) | 0.021 (2) | 0.040 (3) | −0.0005 (18) | 0.022 (2) | −0.0025 (18) |
C312 | 0.039 (3) | 0.032 (2) | 0.036 (3) | 0.0007 (19) | 0.015 (2) | 0.0019 (19) |
C313 | 0.042 (3) | 0.024 (2) | 0.051 (3) | 0.0056 (19) | 0.029 (2) | 0.009 (2) |
C314 | 0.036 (3) | 0.022 (2) | 0.042 (3) | −0.001 (2) | 0.022 (3) | −0.005 (2) |
C315 | 0.028 (2) | 0.024 (2) | 0.037 (2) | −0.0017 (16) | 0.016 (2) | −0.0049 (17) |
B1 | 0.027 (3) | 0.028 (2) | 0.033 (3) | 0.000 (2) | 0.010 (2) | −0.004 (2) |
F11 | 0.0448 (18) | 0.0604 (19) | 0.081 (2) | −0.0066 (14) | 0.0031 (16) | −0.0388 (17) |
F12 | 0.0363 (16) | 0.0642 (18) | 0.055 (2) | −0.0010 (14) | 0.0115 (15) | 0.0269 (15) |
F13 | 0.062 (2) | 0.066 (2) | 0.064 (2) | 0.0072 (16) | 0.0450 (18) | 0.0054 (16) |
F14 | 0.0491 (17) | 0.0326 (13) | 0.0497 (16) | 0.0064 (11) | 0.0077 (14) | 0.0032 (12) |
B2 | 0.027 (3) | 0.025 (2) | 0.032 (3) | −0.004 (2) | 0.002 (2) | 0.000 (2) |
F21 | 0.041 (2) | 0.093 (3) | 0.0428 (19) | 0.0010 (15) | 0.0145 (16) | −0.0233 (15) |
F22 | 0.050 (2) | 0.074 (2) | 0.054 (2) | −0.0109 (14) | 0.0304 (18) | −0.0020 (14) |
F23 | 0.0445 (16) | 0.0327 (14) | 0.0502 (16) | −0.0044 (11) | 0.0001 (13) | −0.0021 (11) |
F24 | 0.063 (2) | 0.0459 (19) | 0.101 (3) | −0.0005 (14) | −0.0212 (19) | 0.0309 (18) |
I1—N11 | 2.255 (3) | C211—H211 | 0.9500 |
I1—N12 | 2.261 (3) | C212—C213 | 1.397 (9) |
N11—C115 | 1.336 (5) | C212—H212 | 0.9500 |
N11—C111 | 1.355 (6) | C213—C214 | 1.377 (7) |
C111—C112 | 1.365 (6) | C213—H213 | 0.9500 |
C111—H111 | 0.9500 | C214—C215 | 1.373 (6) |
C112—C113 | 1.389 (6) | C214—H214 | 0.9500 |
C112—H112 | 0.9500 | C215—H215 | 0.9500 |
C113—C114 | 1.369 (7) | I3—N31 | 2.261 (3) |
C113—H113 | 0.9500 | I3—N31ii | 2.261 (3) |
C114—C115 | 1.365 (6) | N31—C315 | 1.342 (5) |
C114—H114 | 0.9500 | N31—C311 | 1.348 (5) |
C115—H115 | 0.9500 | C311—C312 | 1.372 (6) |
N12—C125 | 1.340 (5) | C311—H311 | 0.9500 |
N12—C121 | 1.341 (5) | C312—C313 | 1.387 (6) |
C121—C122 | 1.378 (6) | C312—H312 | 0.9500 |
C121—H121 | 0.9500 | C313—C314 | 1.384 (7) |
C122—C123 | 1.365 (7) | C313—H313 | 0.9500 |
C122—H122 | 0.9500 | C314—C315 | 1.365 (6) |
C123—C124 | 1.388 (8) | C314—H314 | 0.9500 |
C123—H123 | 0.9500 | C315—H315 | 0.9500 |
C124—C125 | 1.374 (6) | B1—F13 | 1.372 (5) |
C124—H124 | 0.9500 | B1—F11 | 1.379 (5) |
C125—H125 | 0.9500 | B1—F12 | 1.385 (5) |
I2—N21i | 2.260 (3) | B1—F14 | 1.389 (5) |
I2—N21 | 2.260 (3) | B2—F21 | 1.369 (6) |
N21—C215 | 1.327 (5) | B2—F22 | 1.378 (6) |
N21—C211 | 1.337 (5) | B2—F24 | 1.378 (5) |
C211—C212 | 1.376 (6) | B2—F23 | 1.390 (5) |
N11—I1—N12 | 177.66 (12) | C211—C212—C213 | 119.1 (5) |
C115—N11—C111 | 119.2 (4) | C211—C212—H212 | 120.5 |
C115—N11—I1 | 121.5 (3) | C213—C212—H212 | 120.5 |
C111—N11—I1 | 119.3 (3) | C214—C213—C212 | 118.5 (4) |
N11—C111—C112 | 121.5 (4) | C214—C213—H213 | 120.8 |
N11—C111—H111 | 119.2 | C212—C213—H213 | 120.8 |
C112—C111—H111 | 119.2 | C215—C214—C213 | 119.4 (5) |
C111—C112—C113 | 118.6 (4) | C215—C214—H214 | 120.3 |
C111—C112—H112 | 120.7 | C213—C214—H214 | 120.3 |
C113—C112—H112 | 120.7 | N21—C215—C214 | 121.6 (4) |
C114—C113—C112 | 119.5 (4) | N21—C215—H215 | 119.2 |
C114—C113—H113 | 120.2 | C214—C215—H215 | 119.2 |
C112—C113—H113 | 120.2 | N31—I3—N31ii | 180.0 |
C115—C114—C113 | 119.3 (4) | C315—N31—C311 | 119.4 (3) |
C115—C114—H114 | 120.3 | C315—N31—I3 | 120.6 (3) |
C113—C114—H114 | 120.3 | C311—N31—I3 | 119.9 (3) |
N11—C115—C114 | 121.8 (4) | N31—C311—C312 | 121.7 (4) |
N11—C115—H115 | 119.1 | N31—C311—H311 | 119.1 |
C114—C115—H115 | 119.1 | C312—C311—H311 | 119.1 |
C125—N12—C121 | 120.2 (4) | C311—C312—C313 | 119.0 (4) |
C125—N12—I1 | 118.9 (3) | C311—C312—H312 | 120.5 |
C121—N12—I1 | 120.9 (3) | C313—C312—H312 | 120.5 |
N12—C121—C122 | 120.7 (4) | C314—C313—C312 | 118.6 (4) |
N12—C121—H121 | 119.7 | C314—C313—H313 | 120.7 |
C122—C121—H121 | 119.7 | C312—C313—H313 | 120.7 |
C123—C122—C121 | 120.1 (5) | C315—C314—C313 | 119.9 (4) |
C123—C122—H122 | 120.0 | C315—C314—H314 | 120.1 |
C121—C122—H122 | 120.0 | C313—C314—H314 | 120.1 |
C122—C123—C124 | 118.7 (4) | N31—C315—C314 | 121.4 (4) |
C122—C123—H123 | 120.7 | N31—C315—H315 | 119.3 |
C124—C123—H123 | 120.7 | C314—C315—H315 | 119.3 |
C125—C124—C123 | 119.4 (5) | F13—B1—F11 | 110.9 (4) |
C125—C124—H124 | 120.3 | F13—B1—F12 | 108.6 (4) |
C123—C124—H124 | 120.3 | F11—B1—F12 | 108.1 (4) |
N12—C125—C124 | 121.0 (4) | F13—B1—F14 | 110.8 (4) |
N12—C125—H125 | 119.5 | F11—B1—F14 | 109.8 (4) |
C124—C125—H125 | 119.5 | F12—B1—F14 | 108.7 (4) |
N21i—I2—N21 | 180.0 | F21—B2—F22 | 109.3 (4) |
C215—N21—C211 | 120.3 (4) | F21—B2—F24 | 108.5 (4) |
C215—N21—I2 | 120.7 (3) | F22—B2—F24 | 109.9 (4) |
C211—N21—I2 | 119.0 (3) | F21—B2—F23 | 109.4 (4) |
N21—C211—C212 | 121.1 (4) | F22—B2—F23 | 109.6 (4) |
N21—C211—H211 | 119.4 | F24—B2—F23 | 110.2 (4) |
C212—C211—H211 | 119.4 | ||
C115—N11—C111—C112 | 1.2 (6) | C215—N21—C211—C212 | −0.2 (6) |
I1—N11—C111—C112 | −178.6 (3) | I2—N21—C211—C212 | −179.8 (3) |
N11—C111—C112—C113 | −0.4 (6) | N21—C211—C212—C213 | 0.8 (7) |
C111—C112—C113—C114 | −0.5 (7) | C211—C212—C213—C214 | −1.2 (7) |
C112—C113—C114—C115 | 0.6 (8) | C212—C213—C214—C215 | 0.9 (7) |
C111—N11—C115—C114 | −1.1 (6) | C211—N21—C215—C214 | −0.1 (6) |
I1—N11—C115—C114 | 178.7 (4) | I2—N21—C215—C214 | 179.5 (3) |
C113—C114—C115—N11 | 0.2 (7) | C213—C214—C215—N21 | −0.3 (7) |
C125—N12—C121—C122 | −0.6 (6) | C315—N31—C311—C312 | 0.6 (6) |
I1—N12—C121—C122 | 177.5 (3) | I3—N31—C311—C312 | −177.5 (3) |
N12—C121—C122—C123 | 0.0 (7) | N31—C311—C312—C313 | 0.0 (6) |
C121—C122—C123—C124 | 0.5 (7) | C311—C312—C313—C314 | −0.7 (6) |
C122—C123—C124—C125 | −0.5 (8) | C312—C313—C314—C315 | 1.0 (7) |
C121—N12—C125—C124 | 0.7 (6) | C311—N31—C315—C314 | −0.3 (6) |
I1—N12—C125—C124 | −177.4 (3) | I3—N31—C315—C314 | 177.7 (3) |
C123—C124—C125—N12 | −0.1 (7) | C313—C314—C315—N31 | −0.5 (7) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C10H10IN2+·BF4− |
Mr | 371.91 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 12.1840 (4), 15.7830 (4), 14.8550 (3) |
β (°) | 115.1760 (16) |
V (Å3) | 2585.25 (12) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 19.80 |
Crystal size (mm) | 0.10 × 0.05 × 0.02 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (XABS2 (Parkin et al., 1995) |
Tmin, Tmax | 0.416, 0.673 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9437, 4821, 3369 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.141, 1.10 |
No. of reflections | 4821 |
No. of parameters | 328 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −1.35 |
Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97.
I1—N11 | 2.255 (3) | I2—N21 | 2.260 (3) |
I1—N12 | 2.261 (3) | I3—N31 | 2.261 (3) |
I2—N21i | 2.260 (3) | I3—N31ii | 2.261 (3) |
N11—I1—N12 | 177.66 (12) | N31—I3—N31ii | 180.0 |
N21i—I2—N21 | 180.0 | ||
I1—N11—C115—C114 | 178.7 (4) | I2—N21—C215—C214 | 179.5 (3) |
I1—N12—C125—C124 | −177.4 (3) | I3—N31—C315—C314 | 177.7 (3) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+2, −y+1, −z+2. |
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The title compound, (I), is a well known iodination reagent in organic synthesis (Barluenga et al., 1985; Barluenga, 1999).
The crystal structures of some related compounds have already been published (Hassel & Hope, 1961; Brayer & James, 1982). However, the crystal structure of IPy2BF4 had not been reported to date.
This compound is found to crystallize in the monoclinic space group P21/c. Noteworthy, the I atoms in the crystal cell exhibit a `frustrated' C2/m symmetry which would result in a new cell given by the transformation a' = a, b' = b/2 and c'= c/2, with only one I atom per asymmetric unit. In the actual unit cell (P21/c symmetry), the I atom corresponding to the independent IPy2 molecule (I1) occupies a position with coordinates [0.48947 (3), 0.74618 (2), 0.99242 (2)], quite close to the special position (1/2, 3/4, 1), which could have generated a centred cell. All attempts of solving the crystal structure using the transformed unit cell failed. Furthermore, a careful inspection of the X-ray diffraction pattern by eye, by superimposing the predicted reflections on the experimental ones, revealed that several strong reflections were not being indexed when the centred cell was being imposed. The choice of the primitive cell is reinforced by the fact that the spatial arrangement of the remainder unit-cell contents, that is, the pyridine rings and the counteranions BF4, differs from the pseudosymmetry defined by the I atoms.
The whole IPy2 moiety is basically planar. The torsion angle between the planes of the two pyridines is exactly 0° in those IPy2 moieties in which the I atom (I2 and I3) lies on a centre of symmetry. A slight deviation from this value [9.7 (2)°] is observed in the other independent moiety in the unit cell.