Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017130/ci6151sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017130/ci6151Isup2.hkl |
CCDC reference: 200754
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 10.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.682 0.909 Tmin' and Tmax expected: 0.788 0.943 RR' = 0.898 Please check that your absorption correction is appropriate. PLAT_214 Alert C Atom O31A (Anion/Solvent) ADP max/min Ratio 4.10 prolate PLAT_302 Alert C Anion/Solvent Disorder ....................... 17.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C14H20N33+·3ClO4− | Z = 2 |
Mr = 528.68 | F(000) = 544 |
Triclinic, P1 | Dx = 1.620 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6789 (8) Å | Cell parameters from 56 reflections |
b = 8.7858 (10) Å | θ = 4.8–13.2° |
c = 15.1139 (15) Å | µ = 0.49 mm−1 |
α = 105.984 (8)° | T = 293 K |
β = 94.188 (8)° | Plate, colorless |
γ = 99.581 (9)° | 0.48 × 0.24 × 0.12 mm |
V = 1083.82 (19) Å3 |
Siemens P4S diffractometer | 2885 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
2θ/ω scans | h = 0→10 |
Absorption correction: part of the refinement model (ΔF) (SHELXTL; Sheldrick, 1997) | k = −9→9 |
Tmin = 0.682, Tmax = 0.909 | l = −17→17 |
4007 measured reflections | 3 standard reflections every 97 reflections |
3743 independent reflections | intensity decay: 0.9% |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.8913P] where P = (Fo2 + 2Fc2)/3 |
3743 reflections | (Δ/σ)max = 0.027 |
365 parameters | Δρmax = 0.29 e Å−3 |
121 restraints | Δρmin = −0.37 e Å−3 |
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) | |
Cl1 | 0.94946 (8) | 0.36638 (8) | 0.19112 (5) | 0.03984 (19) | |
Cl2 | 1.29355 (9) | 0.60854 (10) | 0.46375 (5) | 0.0469 (2) | |
Cl3 | 0.44716 (10) | −0.07948 (11) | 0.16660 (6) | 0.0572 (2) | |
O11 | 0.8503 (3) | 0.3501 (4) | 0.2613 (2) | 0.0797 (9) | |
O12 | 1.0425 (3) | 0.5264 (3) | 0.21648 (18) | 0.0673 (7) | |
O13 | 0.8532 (3) | 0.3371 (3) | 0.10462 (17) | 0.0617 (6) | |
O14 | 1.0501 (2) | 0.2515 (3) | 0.18211 (17) | 0.0540 (6) | |
O21 | 1.3672 (4) | 0.7165 (3) | 0.4178 (2) | 0.0834 (9) | |
O22 | 1.1265 (3) | 0.5846 (4) | 0.4426 (2) | 0.0839 (9) | |
O23 | 1.3344 (4) | 0.6695 (4) | 0.56077 (17) | 0.0778 (8) | |
O24 | 1.3432 (3) | 0.4571 (3) | 0.43013 (17) | 0.0623 (7) | |
O31 | 0.5179 (6) | 0.0377 (6) | 0.1257 (4) | 0.080 (2) | 0.510 (4) |
O32 | 0.5076 (10) | −0.2205 (6) | 0.1353 (5) | 0.117 (3) | 0.510 (4) |
O33 | 0.2830 (4) | −0.1106 (11) | 0.1422 (5) | 0.136 (4) | 0.510 (4) |
O34 | 0.4825 (8) | −0.0177 (9) | 0.2640 (2) | 0.121 (3) | 0.510 (4) |
O31A | 0.4320 (11) | −0.0606 (16) | 0.0770 (4) | 0.161 (9) | 0.358 (10) |
O32A | 0.5907 (8) | −0.1295 (15) | 0.1824 (7) | 0.091 (4) | 0.358 (10) |
O33A | 0.3217 (10) | −0.2003 (10) | 0.1728 (8) | 0.117 (5) | 0.358 (10) |
O34A | 0.4441 (14) | 0.0662 (7) | 0.2333 (7) | 0.137 (7) | 0.358 (10) |
O31B | 0.337 (3) | 0.018 (3) | 0.1993 (17) | 0.091 (13) | 0.131 (10) |
O32B | 0.410 (4) | −0.2263 (16) | 0.1883 (18) | 0.123 (13) | 0.131 (10) |
O33B | 0.5998 (15) | 0.001 (4) | 0.2089 (16) | 0.19 (2) | 0.131 (10) |
O34B | 0.440 (3) | −0.111 (3) | 0.0695 (3) | 0.091 (11) | 0.131 (10) |
N1A | 1.0282 (3) | 0.8252 (3) | 0.36280 (18) | 0.0454 (6) | |
H1AA | 1.0527 | 0.7326 | 0.3579 | 0.054* | |
N1B | 0.2929 (3) | 0.1579 (3) | 0.02273 (17) | 0.0392 (6) | |
H1BA | 0.3506 | 0.1064 | 0.0476 | 0.047* | |
N | 0.5606 (3) | 0.4690 (3) | 0.29318 (16) | 0.0383 (6) | |
H0A | 0.5271 | 0.4737 | 0.3487 | 0.046* | |
H0B | 0.6237 | 0.3961 | 0.2823 | 0.046* | |
C2A | 1.1386 (4) | 0.9432 (4) | 0.3526 (3) | 0.0572 (9) | |
H2AA | 1.2386 | 0.9243 | 0.3413 | 0.069* | |
C3A | 1.1036 (5) | 1.0907 (4) | 0.3591 (2) | 0.0568 (9) | |
H3AA | 1.1785 | 1.1737 | 0.3516 | 0.068* | |
C4A | 0.9555 (5) | 1.1143 (4) | 0.3767 (2) | 0.0599 (10) | |
H4AA | 0.9293 | 1.2143 | 0.3813 | 0.072* | |
C5A | 0.8456 (4) | 0.9917 (4) | 0.3879 (2) | 0.0523 (8) | |
H5AA | 0.7458 | 1.0095 | 0.4007 | 0.063* | |
C6A | 0.8820 (3) | 0.8426 (3) | 0.38010 (18) | 0.0368 (6) | |
C7A | 0.7710 (4) | 0.6977 (4) | 0.3865 (2) | 0.0468 (8) | |
H7AA | 0.7145 | 0.7274 | 0.4397 | 0.056* | |
H7AB | 0.8295 | 0.6164 | 0.3944 | 0.056* | |
C8A | 0.6548 (3) | 0.6299 (4) | 0.2982 (2) | 0.0402 (7) | |
H8AA | 0.5843 | 0.7042 | 0.2963 | 0.048* | |
H8AB | 0.7119 | 0.6200 | 0.2447 | 0.048* | |
C2B | 0.1740 (4) | 0.0726 (4) | −0.0409 (2) | 0.0502 (8) | |
H2BA | 0.1557 | −0.0395 | −0.0580 | 0.060* | |
C3B | 0.0789 (4) | 0.1492 (4) | −0.0813 (2) | 0.0534 (8) | |
H3BA | −0.0047 | 0.0905 | −0.1263 | 0.064* | |
C4B | 0.1083 (4) | 0.3154 (4) | −0.0543 (2) | 0.0534 (9) | |
H4BA | 0.0428 | 0.3700 | −0.0800 | 0.064* | |
C5B | 0.2348 (4) | 0.4010 (4) | 0.0109 (2) | 0.0439 (7) | |
H5BA | 0.2566 | 0.5132 | 0.0278 | 0.053* | |
C6B | 0.3291 (3) | 0.3198 (3) | 0.05089 (18) | 0.0339 (6) | |
C7B | 0.4678 (3) | 0.3977 (4) | 0.1235 (2) | 0.0415 (7) | |
H7BA | 0.5099 | 0.5043 | 0.1190 | 0.050* | |
H7BB | 0.5495 | 0.3340 | 0.1130 | 0.050* | |
C8B | 0.4205 (3) | 0.4115 (4) | 0.21985 (19) | 0.0378 (6) | |
H8BA | 0.3487 | 0.4862 | 0.2331 | 0.045* | |
H8BB | 0.3654 | 0.3069 | 0.2214 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0370 (4) | 0.0409 (4) | 0.0431 (4) | 0.0124 (3) | 0.0062 (3) | 0.0117 (3) |
Cl2 | 0.0502 (5) | 0.0582 (5) | 0.0424 (4) | 0.0236 (4) | 0.0111 (3) | 0.0225 (4) |
Cl3 | 0.0606 (5) | 0.0681 (6) | 0.0558 (5) | 0.0250 (4) | 0.0141 (4) | 0.0298 (4) |
O11 | 0.0690 (17) | 0.122 (2) | 0.0814 (19) | 0.0498 (17) | 0.0430 (15) | 0.0562 (18) |
O12 | 0.0842 (18) | 0.0371 (13) | 0.0682 (16) | 0.0013 (12) | −0.0068 (14) | 0.0053 (11) |
O13 | 0.0585 (15) | 0.0638 (15) | 0.0585 (15) | 0.0086 (12) | −0.0144 (12) | 0.0183 (12) |
O14 | 0.0431 (12) | 0.0473 (13) | 0.0741 (16) | 0.0202 (10) | 0.0079 (11) | 0.0151 (11) |
O21 | 0.103 (2) | 0.0723 (18) | 0.096 (2) | 0.0217 (16) | 0.0419 (18) | 0.0476 (17) |
O22 | 0.0494 (15) | 0.122 (3) | 0.095 (2) | 0.0315 (16) | 0.0066 (14) | 0.0478 (19) |
O23 | 0.100 (2) | 0.098 (2) | 0.0411 (14) | 0.0552 (18) | 0.0016 (13) | 0.0097 (13) |
O24 | 0.0730 (17) | 0.0533 (14) | 0.0672 (16) | 0.0254 (13) | 0.0200 (13) | 0.0175 (12) |
O31 | 0.071 (4) | 0.084 (4) | 0.121 (6) | 0.032 (3) | 0.026 (4) | 0.075 (4) |
O32 | 0.187 (9) | 0.055 (4) | 0.152 (8) | 0.066 (5) | 0.099 (7) | 0.056 (5) |
O33 | 0.050 (4) | 0.223 (12) | 0.158 (9) | 0.008 (6) | −0.021 (5) | 0.112 (9) |
O34 | 0.129 (7) | 0.174 (9) | 0.053 (4) | 0.042 (6) | 0.007 (4) | 0.012 (5) |
O31A | 0.208 (16) | 0.31 (2) | 0.078 (9) | 0.227 (17) | 0.080 (9) | 0.119 (11) |
O32A | 0.099 (8) | 0.117 (10) | 0.098 (8) | 0.061 (7) | 0.020 (6) | 0.072 (7) |
O33A | 0.097 (10) | 0.121 (10) | 0.126 (10) | −0.008 (7) | 0.030 (8) | 0.037 (7) |
O34A | 0.173 (17) | 0.062 (7) | 0.170 (15) | 0.036 (8) | 0.040 (13) | 0.013 (7) |
O31B | 0.13 (3) | 0.08 (2) | 0.09 (2) | 0.06 (2) | 0.08 (2) | 0.039 (17) |
O32B | 0.148 (17) | 0.108 (15) | 0.134 (16) | 0.042 (10) | −0.004 (10) | 0.064 (10) |
O33B | 0.18 (2) | 0.19 (2) | 0.19 (2) | 0.035 (11) | 0.017 (10) | 0.048 (12) |
O34B | 0.087 (14) | 0.108 (14) | 0.082 (14) | 0.045 (9) | 0.020 (9) | 0.014 (8) |
N1A | 0.0516 (16) | 0.0374 (14) | 0.0511 (16) | 0.0165 (12) | 0.0119 (12) | 0.0132 (12) |
N1B | 0.0416 (14) | 0.0364 (14) | 0.0430 (14) | 0.0142 (11) | 0.0057 (11) | 0.0132 (11) |
N | 0.0311 (12) | 0.0485 (15) | 0.0373 (13) | 0.0058 (11) | 0.0019 (10) | 0.0177 (11) |
C2A | 0.050 (2) | 0.062 (2) | 0.066 (2) | 0.0105 (17) | 0.0195 (17) | 0.0261 (18) |
C3A | 0.070 (2) | 0.050 (2) | 0.049 (2) | −0.0034 (18) | 0.0101 (17) | 0.0204 (16) |
C4A | 0.092 (3) | 0.0391 (19) | 0.054 (2) | 0.0233 (19) | 0.0093 (19) | 0.0171 (16) |
C5A | 0.054 (2) | 0.052 (2) | 0.056 (2) | 0.0239 (17) | 0.0070 (16) | 0.0152 (16) |
C6A | 0.0395 (16) | 0.0424 (16) | 0.0263 (14) | 0.0085 (13) | −0.0019 (12) | 0.0078 (12) |
C7A | 0.0454 (18) | 0.0532 (19) | 0.0388 (17) | −0.0006 (15) | −0.0043 (14) | 0.0166 (14) |
C8A | 0.0360 (15) | 0.0440 (17) | 0.0401 (16) | 0.0020 (13) | −0.0019 (13) | 0.0166 (13) |
C2B | 0.055 (2) | 0.0390 (17) | 0.0470 (19) | 0.0017 (15) | 0.0043 (16) | 0.0023 (14) |
C3B | 0.0475 (19) | 0.062 (2) | 0.0415 (18) | −0.0016 (16) | −0.0032 (15) | 0.0093 (16) |
C4B | 0.0471 (19) | 0.071 (2) | 0.052 (2) | 0.0195 (17) | 0.0011 (16) | 0.0312 (18) |
C5B | 0.0512 (18) | 0.0373 (16) | 0.0477 (18) | 0.0110 (14) | 0.0084 (15) | 0.0177 (14) |
C6B | 0.0335 (15) | 0.0382 (16) | 0.0306 (14) | 0.0077 (12) | 0.0089 (11) | 0.0092 (12) |
C7B | 0.0342 (15) | 0.0470 (18) | 0.0395 (16) | 0.0017 (13) | 0.0037 (13) | 0.0103 (13) |
C8B | 0.0269 (14) | 0.0475 (17) | 0.0371 (16) | 0.0035 (12) | 0.0026 (12) | 0.0116 (13) |
Cl1—O14 | 1.426 (2) | Cl3—O31 | 1.420 (3) |
Cl1—O12 | 1.434 (2) | N1A—C6A | 1.339 (4) |
Cl1—O13 | 1.434 (2) | N1A—C2A | 1.340 (4) |
Cl1—O11 | 1.436 (2) | N1B—C2B | 1.323 (4) |
Cl2—O23 | 1.411 (3) | N1B—C6B | 1.341 (4) |
Cl2—O21 | 1.420 (3) | N—C8A | 1.490 (4) |
Cl2—O22 | 1.429 (3) | N—C8B | 1.501 (3) |
Cl2—O24 | 1.437 (2) | C2A—C3A | 1.359 (5) |
Cl3—O34A | 1.400 (3) | C3A—C4A | 1.369 (5) |
Cl3—O32 | 1.401 (3) | C4A—C5A | 1.371 (5) |
Cl3—O33 | 1.406 (3) | C5A—C6A | 1.374 (4) |
Cl3—O33B | 1.407 (4) | C6A—C7A | 1.494 (4) |
Cl3—O31A | 1.409 (3) | C7A—C8A | 1.522 (4) |
Cl3—O32B | 1.410 (4) | C2B—C3B | 1.358 (5) |
Cl3—O34B | 1.410 (4) | C3B—C4B | 1.377 (5) |
Cl3—O31B | 1.411 (4) | C4B—C5B | 1.378 (4) |
Cl3—O34 | 1.412 (3) | C5B—C6B | 1.380 (4) |
Cl3—O32A | 1.414 (3) | C6B—C7B | 1.497 (4) |
Cl3—O33A | 1.416 (3) | C7B—C8B | 1.521 (4) |
O14—Cl1—O12 | 109.79 (15) | O32A—Cl3—O33A | 108.5 (2) |
O14—Cl1—O13 | 109.80 (15) | O32—Cl3—O31 | 109.3 (2) |
O12—Cl1—O13 | 109.11 (15) | O33—Cl3—O31 | 108.9 (2) |
O14—Cl1—O11 | 108.85 (15) | O34—Cl3—O31 | 108.9 (2) |
O12—Cl1—O11 | 109.95 (18) | C6A—N1A—C2A | 124.0 (3) |
O13—Cl1—O11 | 109.33 (17) | C2B—N1B—C6B | 124.2 (3) |
O23—Cl2—O21 | 111.3 (2) | C8A—N—C8B | 114.4 (2) |
O23—Cl2—O22 | 109.05 (18) | N1A—C2A—C3A | 119.7 (3) |
O21—Cl2—O22 | 109.24 (18) | C2A—C3A—C4A | 118.4 (3) |
O23—Cl2—O24 | 109.77 (15) | C3A—C4A—C5A | 120.6 (3) |
O21—Cl2—O24 | 108.16 (16) | C4A—C5A—C6A | 120.3 (3) |
O22—Cl2—O24 | 109.30 (18) | N1A—C6A—C5A | 117.0 (3) |
O32—Cl3—O33 | 110.8 (2) | N1A—C6A—C7A | 117.5 (3) |
O34A—Cl3—O31A | 110.3 (3) | C5A—C6A—C7A | 125.5 (3) |
O33B—Cl3—O32B | 109.6 (3) | C6A—C7A—C8A | 109.4 (2) |
O33B—Cl3—O34B | 109.6 (3) | N—C8A—C7A | 111.5 (2) |
O32B—Cl3—O34B | 109.4 (3) | N1B—C2B—C3B | 119.9 (3) |
O33B—Cl3—O31B | 109.6 (3) | C2B—C3B—C4B | 118.8 (3) |
O32B—Cl3—O31B | 109.3 (3) | C3B—C4B—C5B | 120.0 (3) |
O34B—Cl3—O31B | 109.3 (3) | C4B—C5B—C6B | 119.8 (3) |
O32—Cl3—O34 | 109.7 (2) | N1B—C6B—C5B | 117.3 (3) |
O33—Cl3—O34 | 109.3 (2) | N1B—C6B—C7B | 117.4 (2) |
O34A—Cl3—O32A | 110.0 (3) | C5B—C6B—C7B | 125.3 (3) |
O31A—Cl3—O32A | 109.1 (2) | C6B—C7B—C8B | 110.7 (2) |
O34A—Cl3—O33A | 109.6 (3) | N—C8B—C7B | 111.9 (2) |
O31A—Cl3—O33A | 109.3 (3) | ||
C6A—N1A—C2A—C3A | −0.6 (5) | C6B—N1B—C2B—C3B | −0.7 (5) |
N1A—C2A—C3A—C4A | 0.6 (5) | N1B—C2B—C3B—C4B | −0.3 (5) |
C2A—C3A—C4A—C5A | 0.1 (5) | C2B—C3B—C4B—C5B | 1.6 (5) |
C3A—C4A—C5A—C6A | −0.9 (5) | C3B—C4B—C5B—C6B | −1.9 (5) |
C2A—N1A—C6A—C5A | −0.2 (4) | C2B—N1B—C6B—C5B | 0.4 (4) |
C2A—N1A—C6A—C7A | 178.0 (3) | C2B—N1B—C6B—C7B | −179.9 (3) |
C4A—C5A—C6A—N1A | 0.9 (5) | C4B—C5B—C6B—N1B | 0.9 (4) |
C4A—C5A—C6A—C7A | −177.1 (3) | C4B—C5B—C6B—C7B | −178.8 (3) |
N1A—C6A—C7A—C8A | −104.3 (3) | N1B—C6B—C7B—C8B | −83.8 (3) |
C5A—C6A—C7A—C8A | 73.7 (4) | C5B—C6B—C7B—C8B | 95.9 (3) |
C8B—N—C8A—C7A | 167.1 (2) | C8A—N—C8B—C7B | 59.3 (3) |
C6A—C7A—C8A—N | 169.6 (2) | C6B—C7B—C8B—N | 172.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O22 | 0.86 | 2.19 | 2.916 (4) | 142 |
N1A—H1AA···O12 | 0.86 | 2.38 | 2.957 (3) | 125 |
N1B—H1BA···O31A | 0.86 | 1.87 | 2.704 (9) | 162 |
N1B—H1BA···O31 | 0.86 | 2.07 | 2.915 (6) | 166 |
N1B—H1BA···O34B | 0.86 | 2.27 | 3.09 (2) | 157 |
N—H0A···O24i | 0.90 | 2.10 | 2.912 (3) | 150 |
N—H0A···O23ii | 0.90 | 2.47 | 2.957 (3) | 114 |
N—H0B···O11 | 0.90 | 2.10 | 2.902 (3) | 148 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1. |
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