Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033095/fl2047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033095/fl2047Isup2.hkl |
CCDC reference: 621311
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- R factor = 0.025
- wR factor = 0.051
- Data-to-parameter ratio = 24.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.53 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Hooft, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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); software used to prepare material for publication: WinGX (Farrugia, 1999).
C18H36N3+·I− | F(000) = 872 |
Mr = 421.4 | Dx = 1.41 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 26808 reflections |
a = 20.336 (4) Å | θ = 3.6–28.2° |
b = 7.0062 (14) Å | µ = 1.62 mm−1 |
c = 14.748 (3) Å | T = 123 K |
β = 109.17 (3)° | Plate, colourless |
V = 1984.8 (7) Å3 | 0.12 × 0.05 × 0.01 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3967 reflections with I > 2σ(I) |
CCD rotation images in φ and ω thick slices scans | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | θmax = 28.2°, θmin = 3.6° |
Tmin = 0.830, Tmax = 0.984 | h = −26→27 |
26808 measured reflections | k = −9→9 |
4830 independent reflections | l = −19→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0173P)2 + 1.4994P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.051 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.62 e Å−3 |
4830 reflections | Δρmin = −0.42 e Å−3 |
200 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. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.324248 (7) | 0.181043 (18) | 0.478356 (9) | 0.01927 (5) | |
C10 | 0.19967 (11) | 0.6999 (3) | 0.44233 (14) | 0.0212 (4) | |
H10A | 0.2024 | 0.8381 | 0.442 | 0.025* | |
H10B | 0.2311 | 0.6508 | 0.4106 | 0.025* | |
C14 | 0.00758 (10) | 0.7381 (3) | 0.11968 (14) | 0.0188 (4) | |
H14A | 0.0439 | 0.7196 | 0.0912 | 0.023* | |
H14B | 0.0017 | 0.8745 | 0.1255 | 0.023* | |
C12 | 0.10128 (11) | 0.7237 (3) | 0.28406 (14) | 0.0192 (4) | |
H12A | 0.0986 | 0.8613 | 0.289 | 0.023* | |
H12B | 0.136 | 0.6958 | 0.2538 | 0.023* | |
C13 | 0.03114 (10) | 0.6500 (3) | 0.21971 (13) | 0.0181 (4) | |
H13A | −0.0036 | 0.6766 | 0.25 | 0.022* | |
H13B | 0.0339 | 0.5126 | 0.2137 | 0.022* | |
C11 | 0.12559 (10) | 0.6395 (3) | 0.38507 (14) | 0.0181 (4) | |
H11A | 0.0943 | 0.6807 | 0.4187 | 0.022* | |
H11B | 0.1234 | 0.5014 | 0.3807 | 0.022* | |
N1 | 0.33086 (8) | 0.6450 (2) | 0.69933 (11) | 0.0128 (3) | |
C8 | 0.29932 (10) | 0.6929 (3) | 0.59451 (13) | 0.0166 (4) | |
H8A | 0.3276 | 0.6347 | 0.5604 | 0.02* | |
H8B | 0.3018 | 0.8301 | 0.5873 | 0.02* | |
C1 | 0.34241 (10) | 0.4351 (3) | 0.71699 (13) | 0.0152 (4) | |
H1A | 0.3116 | 0.3616 | 0.6644 | 0.018* | |
H1B | 0.3349 | 0.3978 | 0.7762 | 0.018* | |
C2 | 0.41865 (11) | 0.4060 (3) | 0.72408 (15) | 0.0229 (5) | |
H2A | 0.4369 | 0.2893 | 0.7585 | 0.027* | |
H2B | 0.4231 | 0.3991 | 0.6607 | 0.027* | |
C9 | 0.22433 (10) | 0.6307 (3) | 0.54644 (13) | 0.0178 (4) | |
H9A | 0.1951 | 0.6844 | 0.5803 | 0.021* | |
H9B | 0.2211 | 0.4927 | 0.5482 | 0.021* | |
C15 | −0.06027 (11) | 0.6547 (3) | 0.05249 (14) | 0.0194 (4) | |
H15A | −0.0544 | 0.5185 | 0.0464 | 0.023* | |
H15B | −0.0966 | 0.6729 | 0.0809 | 0.023* | |
C16 | −0.08343 (11) | 0.7439 (3) | −0.04698 (14) | 0.0185 (4) | |
H16A | −0.0463 | 0.7293 | −0.0743 | 0.022* | |
H16B | −0.0906 | 0.8795 | −0.0408 | 0.022* | |
C17 | −0.14981 (11) | 0.6586 (3) | −0.11607 (14) | 0.0211 (4) | |
H17A | −0.1429 | 0.5229 | −0.1226 | 0.025* | |
H17B | −0.1872 | 0.6738 | −0.0893 | 0.025* | |
C18 | −0.17136 (12) | 0.7504 (4) | −0.21489 (15) | 0.0270 (5) | |
H18A | −0.1801 | 0.8838 | −0.2093 | 0.04* | |
H18B | −0.2129 | 0.69 | −0.2558 | 0.04* | |
H18C | −0.1347 | 0.7355 | −0.2419 | 0.04* | |
N2 | 0.45588 (9) | 0.5732 (3) | 0.77660 (12) | 0.0222 (4) | |
N3 | 0.41461 (10) | 0.8623 (3) | 0.81252 (13) | 0.0269 (4) | |
C7 | 0.41263 (11) | 0.7308 (3) | 0.73925 (15) | 0.0201 (4) | |
H7 | 0.425 | 0.7922 | 0.6874 | 0.024* | |
C6 | 0.29765 (11) | 0.7503 (3) | 0.76126 (15) | 0.0194 (4) | |
H6A | 0.2985 | 0.6748 | 0.8168 | 0.023* | |
H6B | 0.2498 | 0.7835 | 0.7256 | 0.023* | |
C3 | 0.46978 (12) | 0.5704 (4) | 0.88171 (15) | 0.0303 (5) | |
H3A | 0.5191 | 0.5532 | 0.9157 | 0.036* | |
H3B | 0.4443 | 0.4676 | 0.8992 | 0.036* | |
C5 | 0.34292 (12) | 0.9293 (3) | 0.79117 (17) | 0.0292 (5) | |
H5A | 0.3312 | 1.0221 | 0.7395 | 0.035* | |
H5B | 0.3366 | 0.9874 | 0.8474 | 0.035* | |
C4 | 0.44543 (14) | 0.7612 (4) | 0.90534 (16) | 0.0387 (6) | |
H4A | 0.4109 | 0.7445 | 0.9371 | 0.046* | |
H4B | 0.4842 | 0.8332 | 0.9474 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02801 (8) | 0.01655 (7) | 0.01351 (7) | −0.00006 (6) | 0.00716 (5) | −0.00026 (5) |
C10 | 0.0216 (11) | 0.0238 (11) | 0.0159 (10) | −0.0026 (9) | 0.0029 (8) | 0.0054 (8) |
C14 | 0.0181 (11) | 0.0200 (10) | 0.0165 (10) | 0.0020 (8) | 0.0033 (8) | 0.0017 (8) |
C12 | 0.0195 (11) | 0.0200 (11) | 0.0170 (10) | −0.0001 (8) | 0.0047 (8) | 0.0011 (8) |
C13 | 0.0182 (10) | 0.0183 (11) | 0.0161 (10) | 0.0014 (8) | 0.0032 (8) | 0.0008 (8) |
C11 | 0.0188 (10) | 0.0191 (11) | 0.0155 (10) | 0.0006 (8) | 0.0043 (8) | 0.0011 (8) |
N1 | 0.0140 (8) | 0.0132 (9) | 0.0114 (8) | −0.0010 (6) | 0.0045 (6) | −0.0001 (6) |
C8 | 0.0187 (10) | 0.0190 (10) | 0.0109 (9) | −0.0003 (8) | 0.0032 (7) | 0.0044 (8) |
C1 | 0.0179 (10) | 0.0127 (10) | 0.0134 (9) | −0.0006 (8) | 0.0027 (8) | −0.0001 (7) |
C2 | 0.0173 (11) | 0.0281 (12) | 0.0209 (11) | 0.0053 (9) | 0.0032 (8) | −0.0040 (9) |
C9 | 0.0184 (10) | 0.0193 (10) | 0.0141 (10) | 0.0008 (8) | 0.0031 (8) | 0.0023 (8) |
C15 | 0.0204 (11) | 0.0185 (11) | 0.0176 (10) | 0.0024 (8) | 0.0037 (8) | −0.0003 (8) |
C16 | 0.0187 (11) | 0.0207 (10) | 0.0158 (10) | 0.0031 (8) | 0.0050 (8) | 0.0006 (8) |
C17 | 0.0195 (10) | 0.0227 (11) | 0.0188 (10) | 0.0032 (9) | 0.0032 (8) | −0.0014 (8) |
C18 | 0.0211 (12) | 0.0377 (13) | 0.0195 (11) | 0.0055 (10) | 0.0031 (9) | −0.0001 (10) |
N2 | 0.0145 (9) | 0.0333 (11) | 0.0170 (9) | −0.0026 (8) | 0.0029 (7) | −0.0025 (8) |
N3 | 0.0269 (10) | 0.0291 (11) | 0.0249 (10) | −0.0115 (8) | 0.0088 (8) | −0.0122 (8) |
C7 | 0.0149 (10) | 0.0273 (12) | 0.0187 (10) | −0.0102 (8) | 0.0063 (8) | −0.0056 (8) |
C6 | 0.0206 (11) | 0.0202 (10) | 0.0192 (10) | 0.0004 (9) | 0.0089 (9) | −0.0056 (8) |
C3 | 0.0238 (12) | 0.0463 (16) | 0.0158 (10) | −0.0111 (11) | −0.0004 (9) | −0.0007 (10) |
C5 | 0.0387 (14) | 0.0190 (12) | 0.0303 (12) | −0.0021 (10) | 0.0117 (10) | −0.0085 (9) |
C4 | 0.0309 (14) | 0.0624 (18) | 0.0184 (12) | 0.0019 (13) | 0.0021 (10) | −0.0127 (11) |
C10—C11 | 1.525 (3) | C9—H9B | 0.97 |
C10—C9 | 1.529 (3) | C15—C16 | 1.520 (3) |
C10—H10A | 0.97 | C15—H15A | 0.97 |
C10—H10B | 0.97 | C15—H15B | 0.97 |
C14—C13 | 1.524 (3) | C16—C17 | 1.521 (3) |
C14—C15 | 1.526 (3) | C16—H16A | 0.97 |
C14—H14A | 0.97 | C16—H16B | 0.97 |
C14—H14B | 0.97 | C17—C18 | 1.520 (3) |
C12—C13 | 1.521 (3) | C17—H17A | 0.97 |
C12—C11 | 1.526 (3) | C17—H17B | 0.97 |
C12—H12A | 0.97 | C18—H18A | 0.96 |
C12—H12B | 0.97 | C18—H18B | 0.96 |
C13—H13A | 0.97 | C18—H18C | 0.96 |
C13—H13B | 0.97 | N2—C7 | 1.406 (3) |
C11—H11A | 0.97 | N2—C3 | 1.482 (3) |
C11—H11B | 0.97 | N3—C7 | 1.411 (3) |
N1—C6 | 1.496 (2) | N3—C5 | 1.464 (3) |
N1—C1 | 1.499 (2) | N3—C4 | 1.485 (3) |
N1—C8 | 1.504 (2) | C7—H7 | 0.98 |
N1—C7 | 1.682 (3) | C6—C5 | 1.532 (3) |
C8—C9 | 1.519 (3) | C6—H6A | 0.97 |
C8—H8A | 0.97 | C6—H6B | 0.97 |
C8—H8B | 0.97 | C3—C4 | 1.506 (4) |
C1—C2 | 1.533 (3) | C3—H3A | 0.97 |
C1—H1A | 0.97 | C3—H3B | 0.97 |
C1—H1B | 0.97 | C5—H5A | 0.97 |
C2—N2 | 1.470 (3) | C5—H5B | 0.97 |
C2—H2A | 0.97 | C4—H4A | 0.97 |
C2—H2B | 0.97 | C4—H4B | 0.97 |
C9—H9A | 0.97 | ||
C11—C10—C9 | 114.01 (17) | C16—C15—C14 | 113.38 (17) |
C11—C10—H10A | 108.8 | C16—C15—H15A | 108.9 |
C9—C10—H10A | 108.8 | C14—C15—H15A | 108.9 |
C11—C10—H10B | 108.8 | C16—C15—H15B | 108.9 |
C9—C10—H10B | 108.8 | C14—C15—H15B | 108.9 |
H10A—C10—H10B | 107.6 | H15A—C15—H15B | 107.7 |
C13—C14—C15 | 113.78 (17) | C15—C16—C17 | 114.25 (18) |
C13—C14—H14A | 108.8 | C15—C16—H16A | 108.7 |
C15—C14—H14A | 108.8 | C17—C16—H16A | 108.7 |
C13—C14—H14B | 108.8 | C15—C16—H16B | 108.7 |
C15—C14—H14B | 108.8 | C17—C16—H16B | 108.7 |
H14A—C14—H14B | 107.7 | H16A—C16—H16B | 107.6 |
C13—C12—C11 | 114.52 (17) | C18—C17—C16 | 112.90 (18) |
C13—C12—H12A | 108.6 | C18—C17—H17A | 109 |
C11—C12—H12A | 108.6 | C16—C17—H17A | 109 |
C13—C12—H12B | 108.6 | C18—C17—H17B | 109 |
C11—C12—H12B | 108.6 | C16—C17—H17B | 109 |
H12A—C12—H12B | 107.6 | H17A—C17—H17B | 107.8 |
C12—C13—C14 | 113.52 (17) | C17—C18—H18A | 109.5 |
C12—C13—H13A | 108.9 | C17—C18—H18B | 109.5 |
C14—C13—H13A | 108.9 | H18A—C18—H18B | 109.5 |
C12—C13—H13B | 108.9 | C17—C18—H18C | 109.5 |
C14—C13—H13B | 108.9 | H18A—C18—H18C | 109.5 |
H13A—C13—H13B | 107.7 | H18B—C18—H18C | 109.5 |
C10—C11—C12 | 112.21 (17) | C7—N2—C2 | 105.77 (16) |
C10—C11—H11A | 109.2 | C7—N2—C3 | 107.48 (17) |
C12—C11—H11A | 109.2 | C2—N2—C3 | 115.39 (18) |
C10—C11—H11B | 109.2 | C7—N3—C5 | 105.58 (17) |
C12—C11—H11B | 109.2 | C7—N3—C4 | 106.95 (19) |
H11A—C11—H11B | 107.9 | C5—N3—C4 | 116.12 (19) |
C6—N1—C1 | 117.00 (15) | N2—C7—N3 | 110.85 (18) |
C6—N1—C8 | 113.06 (15) | N2—C7—N1 | 106.00 (16) |
C1—N1—C8 | 112.77 (15) | N3—C7—N1 | 106.13 (15) |
C6—N1—C7 | 101.69 (14) | N2—C7—H7 | 111.2 |
C1—N1—C7 | 102.08 (14) | N3—C7—H7 | 111.2 |
C8—N1—C7 | 108.59 (14) | N1—C7—H7 | 111.2 |
N1—C8—C9 | 116.08 (16) | N1—C6—C5 | 103.31 (16) |
N1—C8—H8A | 108.3 | N1—C6—H6A | 111.1 |
C9—C8—H8A | 108.3 | C5—C6—H6A | 111.1 |
N1—C8—H8B | 108.3 | N1—C6—H6B | 111.1 |
C9—C8—H8B | 108.3 | C5—C6—H6B | 111.1 |
H8A—C8—H8B | 107.4 | H6A—C6—H6B | 109.1 |
N1—C1—C2 | 103.86 (16) | N2—C3—C4 | 105.41 (19) |
N1—C1—H1A | 111 | N2—C3—H3A | 110.7 |
C2—C1—H1A | 111 | C4—C3—H3A | 110.7 |
N1—C1—H1B | 111 | N2—C3—H3B | 110.7 |
C2—C1—H1B | 111 | C4—C3—H3B | 110.7 |
H1A—C1—H1B | 109 | H3A—C3—H3B | 108.8 |
N2—C2—C1 | 105.34 (16) | N3—C5—C6 | 105.16 (17) |
N2—C2—H2A | 110.7 | N3—C5—H5A | 110.7 |
C1—C2—H2A | 110.7 | C6—C5—H5A | 110.7 |
N2—C2—H2B | 110.7 | N3—C5—H5B | 110.7 |
C1—C2—H2B | 110.7 | C6—C5—H5B | 110.7 |
H2A—C2—H2B | 108.8 | H5A—C5—H5B | 108.8 |
C8—C9—C10 | 109.01 (16) | N3—C4—C3 | 106.37 (18) |
C8—C9—H9A | 109.9 | N3—C4—H4A | 110.5 |
C10—C9—H9A | 109.9 | C3—C4—H4A | 110.5 |
C8—C9—H9B | 109.9 | N3—C4—H4B | 110.5 |
C10—C9—H9B | 109.9 | C3—C4—H4B | 110.5 |
H9A—C9—H9B | 108.3 | H4A—C4—H4B | 108.6 |