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
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 |