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The title compound, C18H36IN3, crystallizes in a monoclinic setting. Packing for this compound results in a head-to-head configuration of the cation with the C11 tails orienting themselves in an overlapping multilayer structure. This novel surfactant can be readily hydrolysed to provide a triaza-macrocylic ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033095/fl2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033095/fl2047Isup2.hkl
Contains datablock I

CCDC reference: 621311

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](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

Computing details top

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).

1-Undecyl-4,7-diaza-1-azoniatricyclo[5.2.1.04,10]decane iodide top
Crystal data top
C18H36N3+·IF(000) = 872
Mr = 421.4Dx = 1.41 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 26808 reflections
a = 20.336 (4) Åθ = 3.6–28.2°
b = 7.0062 (14) ŵ = 1.62 mm1
c = 14.748 (3) ÅT = 123 K
β = 109.17 (3)°Plate, colourless
V = 1984.8 (7) Å30.12 × 0.05 × 0.01 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3967 reflections with I > 2σ(I)
CCD rotation images in φ and ω thick slices scansRint = 0.037
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
θmax = 28.2°, θmin = 3.6°
Tmin = 0.830, Tmax = 0.984h = 2627
26808 measured reflectionsk = 99
4830 independent reflectionsl = 1914
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 1.03Δρmax = 0.62 e Å3
4830 reflectionsΔρmin = 0.42 e Å3
200 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.324248 (7)0.181043 (18)0.478356 (9)0.01927 (5)
C100.19967 (11)0.6999 (3)0.44233 (14)0.0212 (4)
H10A0.20240.83810.4420.025*
H10B0.23110.65080.41060.025*
C140.00758 (10)0.7381 (3)0.11968 (14)0.0188 (4)
H14A0.04390.71960.09120.023*
H14B0.00170.87450.12550.023*
C120.10128 (11)0.7237 (3)0.28406 (14)0.0192 (4)
H12A0.09860.86130.2890.023*
H12B0.1360.69580.25380.023*
C130.03114 (10)0.6500 (3)0.21971 (13)0.0181 (4)
H13A0.00360.67660.250.022*
H13B0.03390.51260.21370.022*
C110.12559 (10)0.6395 (3)0.38507 (14)0.0181 (4)
H11A0.09430.68070.41870.022*
H11B0.12340.50140.38070.022*
N10.33086 (8)0.6450 (2)0.69933 (11)0.0128 (3)
C80.29932 (10)0.6929 (3)0.59451 (13)0.0166 (4)
H8A0.32760.63470.56040.02*
H8B0.30180.83010.58730.02*
C10.34241 (10)0.4351 (3)0.71699 (13)0.0152 (4)
H1A0.31160.36160.66440.018*
H1B0.33490.39780.77620.018*
C20.41865 (11)0.4060 (3)0.72408 (15)0.0229 (5)
H2A0.43690.28930.75850.027*
H2B0.42310.39910.66070.027*
C90.22433 (10)0.6307 (3)0.54644 (13)0.0178 (4)
H9A0.19510.68440.58030.021*
H9B0.22110.49270.54820.021*
C150.06027 (11)0.6547 (3)0.05249 (14)0.0194 (4)
H15A0.05440.51850.04640.023*
H15B0.09660.67290.08090.023*
C160.08343 (11)0.7439 (3)0.04698 (14)0.0185 (4)
H16A0.04630.72930.07430.022*
H16B0.09060.87950.04080.022*
C170.14981 (11)0.6586 (3)0.11607 (14)0.0211 (4)
H17A0.14290.52290.12260.025*
H17B0.18720.67380.08930.025*
C180.17136 (12)0.7504 (4)0.21489 (15)0.0270 (5)
H18A0.18010.88380.20930.04*
H18B0.21290.690.25580.04*
H18C0.13470.73550.24190.04*
N20.45588 (9)0.5732 (3)0.77660 (12)0.0222 (4)
N30.41461 (10)0.8623 (3)0.81252 (13)0.0269 (4)
C70.41263 (11)0.7308 (3)0.73925 (15)0.0201 (4)
H70.4250.79220.68740.024*
C60.29765 (11)0.7503 (3)0.76126 (15)0.0194 (4)
H6A0.29850.67480.81680.023*
H6B0.24980.78350.72560.023*
C30.46978 (12)0.5704 (4)0.88171 (15)0.0303 (5)
H3A0.51910.55320.91570.036*
H3B0.44430.46760.89920.036*
C50.34292 (12)0.9293 (3)0.79117 (17)0.0292 (5)
H5A0.33121.02210.73950.035*
H5B0.33660.98740.84740.035*
C40.44543 (14)0.7612 (4)0.90534 (16)0.0387 (6)
H4A0.41090.74450.93710.046*
H4B0.48420.83320.94740.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02801 (8)0.01655 (7)0.01351 (7)0.00006 (6)0.00716 (5)0.00026 (5)
C100.0216 (11)0.0238 (11)0.0159 (10)0.0026 (9)0.0029 (8)0.0054 (8)
C140.0181 (11)0.0200 (10)0.0165 (10)0.0020 (8)0.0033 (8)0.0017 (8)
C120.0195 (11)0.0200 (11)0.0170 (10)0.0001 (8)0.0047 (8)0.0011 (8)
C130.0182 (10)0.0183 (11)0.0161 (10)0.0014 (8)0.0032 (8)0.0008 (8)
C110.0188 (10)0.0191 (11)0.0155 (10)0.0006 (8)0.0043 (8)0.0011 (8)
N10.0140 (8)0.0132 (9)0.0114 (8)0.0010 (6)0.0045 (6)0.0001 (6)
C80.0187 (10)0.0190 (10)0.0109 (9)0.0003 (8)0.0032 (7)0.0044 (8)
C10.0179 (10)0.0127 (10)0.0134 (9)0.0006 (8)0.0027 (8)0.0001 (7)
C20.0173 (11)0.0281 (12)0.0209 (11)0.0053 (9)0.0032 (8)0.0040 (9)
C90.0184 (10)0.0193 (10)0.0141 (10)0.0008 (8)0.0031 (8)0.0023 (8)
C150.0204 (11)0.0185 (11)0.0176 (10)0.0024 (8)0.0037 (8)0.0003 (8)
C160.0187 (11)0.0207 (10)0.0158 (10)0.0031 (8)0.0050 (8)0.0006 (8)
C170.0195 (10)0.0227 (11)0.0188 (10)0.0032 (9)0.0032 (8)0.0014 (8)
C180.0211 (12)0.0377 (13)0.0195 (11)0.0055 (10)0.0031 (9)0.0001 (10)
N20.0145 (9)0.0333 (11)0.0170 (9)0.0026 (8)0.0029 (7)0.0025 (8)
N30.0269 (10)0.0291 (11)0.0249 (10)0.0115 (8)0.0088 (8)0.0122 (8)
C70.0149 (10)0.0273 (12)0.0187 (10)0.0102 (8)0.0063 (8)0.0056 (8)
C60.0206 (11)0.0202 (10)0.0192 (10)0.0004 (9)0.0089 (9)0.0056 (8)
C30.0238 (12)0.0463 (16)0.0158 (10)0.0111 (11)0.0004 (9)0.0007 (10)
C50.0387 (14)0.0190 (12)0.0303 (12)0.0021 (10)0.0117 (10)0.0085 (9)
C40.0309 (14)0.0624 (18)0.0184 (12)0.0019 (13)0.0021 (10)0.0127 (11)
Geometric parameters (Å, º) top
C10—C111.525 (3)C9—H9B0.97
C10—C91.529 (3)C15—C161.520 (3)
C10—H10A0.97C15—H15A0.97
C10—H10B0.97C15—H15B0.97
C14—C131.524 (3)C16—C171.521 (3)
C14—C151.526 (3)C16—H16A0.97
C14—H14A0.97C16—H16B0.97
C14—H14B0.97C17—C181.520 (3)
C12—C131.521 (3)C17—H17A0.97
C12—C111.526 (3)C17—H17B0.97
C12—H12A0.97C18—H18A0.96
C12—H12B0.97C18—H18B0.96
C13—H13A0.97C18—H18C0.96
C13—H13B0.97N2—C71.406 (3)
C11—H11A0.97N2—C31.482 (3)
C11—H11B0.97N3—C71.411 (3)
N1—C61.496 (2)N3—C51.464 (3)
N1—C11.499 (2)N3—C41.485 (3)
N1—C81.504 (2)C7—H70.98
N1—C71.682 (3)C6—C51.532 (3)
C8—C91.519 (3)C6—H6A0.97
C8—H8A0.97C6—H6B0.97
C8—H8B0.97C3—C41.506 (4)
C1—C21.533 (3)C3—H3A0.97
C1—H1A0.97C3—H3B0.97
C1—H1B0.97C5—H5A0.97
C2—N21.470 (3)C5—H5B0.97
C2—H2A0.97C4—H4A0.97
C2—H2B0.97C4—H4B0.97
C9—H9A0.97
C11—C10—C9114.01 (17)C16—C15—C14113.38 (17)
C11—C10—H10A108.8C16—C15—H15A108.9
C9—C10—H10A108.8C14—C15—H15A108.9
C11—C10—H10B108.8C16—C15—H15B108.9
C9—C10—H10B108.8C14—C15—H15B108.9
H10A—C10—H10B107.6H15A—C15—H15B107.7
C13—C14—C15113.78 (17)C15—C16—C17114.25 (18)
C13—C14—H14A108.8C15—C16—H16A108.7
C15—C14—H14A108.8C17—C16—H16A108.7
C13—C14—H14B108.8C15—C16—H16B108.7
C15—C14—H14B108.8C17—C16—H16B108.7
H14A—C14—H14B107.7H16A—C16—H16B107.6
C13—C12—C11114.52 (17)C18—C17—C16112.90 (18)
C13—C12—H12A108.6C18—C17—H17A109
C11—C12—H12A108.6C16—C17—H17A109
C13—C12—H12B108.6C18—C17—H17B109
C11—C12—H12B108.6C16—C17—H17B109
H12A—C12—H12B107.6H17A—C17—H17B107.8
C12—C13—C14113.52 (17)C17—C18—H18A109.5
C12—C13—H13A108.9C17—C18—H18B109.5
C14—C13—H13A108.9H18A—C18—H18B109.5
C12—C13—H13B108.9C17—C18—H18C109.5
C14—C13—H13B108.9H18A—C18—H18C109.5
H13A—C13—H13B107.7H18B—C18—H18C109.5
C10—C11—C12112.21 (17)C7—N2—C2105.77 (16)
C10—C11—H11A109.2C7—N2—C3107.48 (17)
C12—C11—H11A109.2C2—N2—C3115.39 (18)
C10—C11—H11B109.2C7—N3—C5105.58 (17)
C12—C11—H11B109.2C7—N3—C4106.95 (19)
H11A—C11—H11B107.9C5—N3—C4116.12 (19)
C6—N1—C1117.00 (15)N2—C7—N3110.85 (18)
C6—N1—C8113.06 (15)N2—C7—N1106.00 (16)
C1—N1—C8112.77 (15)N3—C7—N1106.13 (15)
C6—N1—C7101.69 (14)N2—C7—H7111.2
C1—N1—C7102.08 (14)N3—C7—H7111.2
C8—N1—C7108.59 (14)N1—C7—H7111.2
N1—C8—C9116.08 (16)N1—C6—C5103.31 (16)
N1—C8—H8A108.3N1—C6—H6A111.1
C9—C8—H8A108.3C5—C6—H6A111.1
N1—C8—H8B108.3N1—C6—H6B111.1
C9—C8—H8B108.3C5—C6—H6B111.1
H8A—C8—H8B107.4H6A—C6—H6B109.1
N1—C1—C2103.86 (16)N2—C3—C4105.41 (19)
N1—C1—H1A111N2—C3—H3A110.7
C2—C1—H1A111C4—C3—H3A110.7
N1—C1—H1B111N2—C3—H3B110.7
C2—C1—H1B111C4—C3—H3B110.7
H1A—C1—H1B109H3A—C3—H3B108.8
N2—C2—C1105.34 (16)N3—C5—C6105.16 (17)
N2—C2—H2A110.7N3—C5—H5A110.7
C1—C2—H2A110.7C6—C5—H5A110.7
N2—C2—H2B110.7N3—C5—H5B110.7
C1—C2—H2B110.7C6—C5—H5B110.7
H2A—C2—H2B108.8H5A—C5—H5B108.8
C8—C9—C10109.01 (16)N3—C4—C3106.37 (18)
C8—C9—H9A109.9N3—C4—H4A110.5
C10—C9—H9A109.9C3—C4—H4A110.5
C8—C9—H9B109.9N3—C4—H4B110.5
C10—C9—H9B109.9C3—C4—H4B110.5
H9A—C9—H9B108.3H4A—C4—H4B108.6
 

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