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The title compound, C18H27N6O4+·Cl-, is the product of addition of two mol­ecules of DABCO (1,4-di­aza­bi­cyclo­[2.2.2]­octane) to one mol­ecule of 1-chloro-2,4-di­nitro­benzene. One of the DABCO mol­ecules undergoes ring opening in the reaction, to give a piperazine ring, one N atom of which is connected to a 2,4-di­nitro­phenyl group, while the other is connected to an intact DABCO moiety via an ethyl­ene linkage. The displaced chloride serves as counter-ion to balance the positive charge on the DABCO quaternary ammonium centre. The crystal structure determination confirms the structure deduced from NMR spectroscopy. Molecular dimensions are unexceptional.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001710/bt6403sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001710/bt64033sup2.hkl
Contains datablock 3

CCDC reference: 234916

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.085
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N2 = 5.32 su PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C4 = 2.96 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

1-{2-[4-(2,4-Dinitrophenyl)piperazin-1-yl]-ethyl}-4-aza-1-azonia- bicyclo[2.2.2]octane chloride top
Crystal data top
C18H27N6O4+·ClF(000) = 904
Mr = 426.91Dx = 1.438 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.9664 (14) ÅCell parameters from 4679 reflections
b = 24.389 (5) Åθ = 2.9–27.5°
c = 11.713 (2) ŵ = 0.23 mm1
β = 97.63 (3)°T = 150 K
V = 1972.4 (7) Å3Block, yellow
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
3439 independent reflections
Radiation source: sealed tube2443 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
φ and ω scansθmax = 25.0°, θmin = 4.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 88
Tmin = 0.93, Tmax = 0.96k = 2929
25990 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0259P)2 + 1.2199P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3439 reflectionsΔρmax = 0.21 e Å3
263 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0028 (7)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.98012 (8)0.70015 (2)0.79270 (5)0.02402 (17)
O10.9758 (2)0.41449 (7)0.89123 (16)0.0378 (5)
O21.1529 (2)0.48746 (7)0.91560 (15)0.0357 (5)
O30.3215 (3)0.42861 (7)0.69357 (17)0.0452 (6)
O40.3004 (2)0.48088 (6)0.54423 (14)0.0269 (4)
N11.0023 (3)0.46361 (8)0.87736 (17)0.0263 (5)
N20.3741 (3)0.46832 (8)0.64141 (18)0.0223 (5)
N30.4321 (3)0.58812 (7)0.60285 (16)0.0196 (4)
N40.1585 (3)0.66049 (7)0.47876 (16)0.0194 (4)
N50.0067 (3)0.78021 (7)0.45569 (15)0.0177 (4)
N60.0598 (3)0.85057 (7)0.60961 (16)0.0232 (5)
C10.8486 (3)0.49533 (9)0.81036 (19)0.0202 (5)
C20.6771 (3)0.47010 (9)0.76672 (19)0.0207 (5)
H20.65390.43280.78370.025*
C30.5399 (3)0.50050 (9)0.69765 (19)0.0173 (5)
C40.5650 (3)0.55670 (9)0.67239 (19)0.0176 (5)
C50.7413 (3)0.57985 (9)0.72283 (19)0.0207 (5)
H50.76510.61750.70910.025*
C60.8797 (3)0.55051 (9)0.79060 (19)0.0212 (5)
H60.99610.56780.82390.025*
C70.2273 (3)0.58943 (9)0.6227 (2)0.0194 (5)
H7A0.21100.61600.68460.023*
H7B0.18820.55280.64760.023*
C80.1009 (3)0.60579 (9)0.5138 (2)0.0211 (6)
H8A0.11500.57890.45210.025*
H8B0.03660.60620.52700.025*
C90.4932 (3)0.64086 (9)0.5604 (2)0.0225 (6)
H9A0.62720.63780.54170.027*
H9B0.49180.66900.62110.027*
C100.3591 (3)0.65811 (9)0.4540 (2)0.0214 (5)
H10A0.39850.69460.42820.026*
H10B0.36890.63160.39100.026*
C110.0254 (3)0.68101 (9)0.3809 (2)0.0211 (5)
H11A0.10890.67270.39440.025*
H11B0.04990.66090.31090.025*
C120.0413 (3)0.74204 (9)0.35869 (19)0.0206 (5)
H12A0.17240.74950.33860.025*
H12B0.05250.75140.29040.025*
C130.1617 (3)0.76198 (9)0.5146 (2)0.0185 (5)
H13A0.12630.72880.56140.022*
H13B0.27400.75300.45660.022*
C140.2142 (3)0.80880 (9)0.5921 (2)0.0247 (6)
H14A0.33600.82620.55660.030*
H14B0.23640.79370.66770.030*
C150.1812 (3)0.78547 (9)0.54612 (19)0.0213 (6)
H15A0.29060.80190.51210.026*
H15B0.22140.74890.57710.026*
C160.1252 (3)0.82251 (9)0.6434 (2)0.0230 (6)
H16A0.11580.79990.71260.028*
H16B0.22810.85020.66360.028*
C170.0352 (3)0.83649 (9)0.4035 (2)0.0229 (6)
H17A0.15860.83570.35070.027*
H17B0.06950.84720.35850.027*
C180.0491 (4)0.87833 (9)0.4999 (2)0.0277 (6)
H18A0.06580.90260.50740.033*
H18B0.16570.90140.48000.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0201 (3)0.0228 (3)0.0280 (3)0.0008 (3)0.0013 (2)0.0013 (3)
O10.0276 (10)0.0270 (11)0.0568 (13)0.0007 (8)0.0016 (9)0.0118 (9)
O20.0208 (10)0.0386 (11)0.0442 (12)0.0032 (8)0.0082 (9)0.0030 (9)
O30.0394 (12)0.0355 (11)0.0552 (13)0.0219 (9)0.0140 (10)0.0225 (10)
O40.0268 (10)0.0307 (10)0.0217 (10)0.0042 (8)0.0019 (8)0.0022 (8)
N10.0229 (12)0.0295 (12)0.0264 (12)0.0009 (10)0.0029 (10)0.0003 (10)
N20.0182 (11)0.0180 (11)0.0309 (13)0.0003 (9)0.0034 (9)0.0028 (10)
N30.0147 (10)0.0162 (10)0.0286 (12)0.0013 (8)0.0053 (9)0.0034 (9)
N40.0142 (10)0.0198 (10)0.0241 (11)0.0013 (8)0.0020 (8)0.0000 (9)
N50.0150 (10)0.0192 (10)0.0182 (10)0.0003 (8)0.0001 (8)0.0010 (8)
N60.0204 (11)0.0207 (11)0.0279 (12)0.0012 (9)0.0015 (9)0.0001 (9)
C10.0181 (13)0.0247 (13)0.0175 (13)0.0014 (10)0.0017 (10)0.0016 (10)
C20.0230 (13)0.0186 (12)0.0212 (13)0.0017 (10)0.0054 (11)0.0003 (11)
C30.0149 (12)0.0179 (12)0.0196 (13)0.0030 (10)0.0040 (10)0.0042 (10)
C40.0162 (12)0.0202 (12)0.0175 (12)0.0001 (10)0.0065 (10)0.0029 (10)
C50.0210 (13)0.0199 (12)0.0221 (13)0.0050 (10)0.0068 (11)0.0034 (11)
C60.0179 (13)0.0255 (13)0.0206 (13)0.0053 (10)0.0031 (10)0.0041 (11)
C70.0149 (12)0.0180 (12)0.0263 (14)0.0025 (10)0.0059 (10)0.0016 (10)
C80.0155 (13)0.0205 (13)0.0282 (14)0.0020 (10)0.0059 (11)0.0054 (11)
C90.0162 (13)0.0196 (12)0.0323 (15)0.0014 (10)0.0054 (11)0.0020 (11)
C100.0188 (13)0.0187 (12)0.0274 (14)0.0017 (10)0.0063 (11)0.0010 (11)
C110.0179 (13)0.0244 (13)0.0203 (13)0.0004 (10)0.0000 (10)0.0030 (10)
C120.0187 (13)0.0277 (13)0.0148 (13)0.0012 (10)0.0001 (10)0.0025 (10)
C130.0157 (12)0.0193 (12)0.0202 (13)0.0022 (10)0.0010 (10)0.0028 (10)
C140.0190 (13)0.0269 (14)0.0287 (14)0.0002 (11)0.0052 (11)0.0002 (11)
C150.0137 (12)0.0239 (13)0.0244 (14)0.0006 (10)0.0044 (10)0.0014 (11)
C160.0198 (13)0.0210 (12)0.0267 (14)0.0006 (10)0.0031 (11)0.0034 (11)
C170.0225 (13)0.0199 (13)0.0256 (14)0.0023 (10)0.0006 (11)0.0084 (11)
C180.0254 (14)0.0195 (13)0.0371 (16)0.0031 (11)0.0008 (12)0.0061 (12)
Geometric parameters (Å, º) top
O1—N11.226 (2)C7—H7B0.990
O2—N11.231 (2)C7—C81.505 (3)
O3—N21.227 (2)C8—H8A0.990
O4—N21.224 (2)C8—H8B0.990
N1—C11.462 (3)C9—H9A0.990
N2—C31.477 (3)C9—H9B0.990
N3—C41.381 (3)C9—C101.515 (3)
N3—C71.476 (3)C10—H10A0.990
N3—C91.462 (3)C10—H10B0.990
N4—C81.467 (3)C11—H11A0.990
N4—C101.466 (3)C11—H11B0.990
N4—C111.463 (3)C11—C121.518 (3)
N5—C121.513 (3)C12—H12A0.990
N5—C131.505 (3)C12—H12B0.990
N5—C151.508 (3)C13—H13A0.990
N5—C171.515 (3)C13—H13B0.990
N6—C141.475 (3)C13—C141.532 (3)
N6—C161.466 (3)C14—H14A0.990
N6—C181.463 (3)C14—H14B0.990
C1—C21.380 (3)C15—H15A0.990
C1—C61.388 (3)C15—H15B0.990
C2—H20.950C15—C161.544 (3)
C2—C31.383 (3)C16—H16A0.990
C3—C41.418 (3)C16—H16B0.990
C4—C51.409 (3)C17—H17A0.990
C5—H50.950C17—H17B0.990
C5—C61.367 (3)C17—C181.535 (3)
C6—H60.950C18—H18A0.990
C7—H7A0.990C18—H18B0.990
O1—N1—O2123.3 (2)H9B—C9—C10109.6
O1—N1—C1118.41 (19)N4—C10—C9110.35 (19)
O2—N1—C1118.3 (2)N4—C10—H10A109.6
O3—N2—O4123.00 (19)N4—C10—H10B109.6
O3—N2—C3117.70 (19)C9—C10—H10A109.6
O4—N2—C3119.23 (19)C9—C10—H10B109.6
C4—N3—C7120.34 (18)H10A—C10—H10B108.1
C4—N3—C9119.10 (18)N4—C11—H11A108.6
C7—N3—C9111.43 (17)N4—C11—H11B108.6
C8—N4—C10108.84 (17)N4—C11—C12114.63 (18)
C8—N4—C11111.18 (17)H11A—C11—H11B107.6
C10—N4—C11112.33 (18)H11A—C11—C12108.6
C12—N5—C13111.98 (17)H11B—C11—C12108.6
C12—N5—C15112.69 (17)N5—C12—C11116.89 (19)
C12—N5—C17107.19 (17)N5—C12—H12A108.1
C13—N5—C15107.93 (17)N5—C12—H12B108.1
C13—N5—C17109.43 (17)C11—C12—H12A108.1
C15—N5—C17107.50 (16)C11—C12—H12B108.1
C14—N6—C16108.27 (17)H12A—C12—H12B107.3
C14—N6—C18108.57 (18)N5—C13—H13A110.1
C16—N6—C18107.88 (19)N5—C13—H13B110.1
N1—C1—C2119.9 (2)N5—C13—C14108.23 (17)
N1—C1—C6118.9 (2)H13A—C13—H13B108.4
C2—C1—C6121.1 (2)H13A—C13—C14110.1
C1—C2—H2120.8H13B—C13—C14110.1
C1—C2—C3118.3 (2)N6—C14—C13111.74 (18)
H2—C2—C3120.8N6—C14—H14A109.3
N2—C3—C2114.52 (19)N6—C14—H14B109.3
N2—C3—C4122.08 (19)C13—C14—H14A109.3
C2—C3—C4123.1 (2)C13—C14—H14B109.3
N3—C4—C3124.6 (2)H14A—C14—H14B107.9
N3—C4—C5120.2 (2)N5—C15—H15A110.1
C3—C4—C5115.1 (2)N5—C15—H15B110.1
C4—C5—H5118.6N5—C15—C16107.98 (17)
C4—C5—C6122.8 (2)H15A—C15—H15B108.4
H5—C5—C6118.6H15A—C15—C16110.1
C1—C6—C5119.4 (2)H15B—C15—C16110.1
C1—C6—H6120.3N6—C16—C15111.93 (18)
C5—C6—H6120.3N6—C16—H16A109.2
N3—C7—H7A109.7N6—C16—H16B109.2
N3—C7—H7B109.7C15—C16—H16A109.2
N3—C7—C8109.99 (19)C15—C16—H16B109.2
H7A—C7—H7B108.2H16A—C16—H16B107.9
H7A—C7—C8109.7N5—C17—H17A109.8
H7B—C7—C8109.7N5—C17—H17B109.8
N4—C8—C7109.07 (18)N5—C17—C18109.42 (18)
N4—C8—H8A109.9H17A—C17—H17B108.2
N4—C8—H8B109.9H17A—C17—C18109.8
C7—C8—H8A109.9H17B—C17—C18109.8
C7—C8—H8B109.9N6—C18—C17110.76 (18)
H8A—C8—H8B108.3N6—C18—H18A109.5
N3—C9—H9A109.6N6—C18—H18B109.5
N3—C9—H9B109.6C17—C18—H18A109.5
N3—C9—C10110.41 (18)C17—C18—H18B109.5
H9A—C9—H9B108.1H18A—C18—H18B108.1
H9A—C9—C10109.6
O1—N1—C1—C21.5 (3)C4—N3—C9—C10158.45 (19)
O1—N1—C1—C6177.7 (2)C7—N3—C9—C1054.5 (2)
O2—N1—C1—C2179.6 (2)C8—N4—C10—C960.8 (2)
O2—N1—C1—C61.3 (3)C11—N4—C10—C9175.65 (17)
N1—C1—C2—C3175.9 (2)N3—C9—C10—N456.8 (2)
C6—C1—C2—C33.2 (3)C8—N4—C11—C12164.80 (19)
C1—C2—C3—N2171.60 (19)C10—N4—C11—C1273.0 (2)
C1—C2—C3—C41.9 (3)C13—N5—C12—C1141.8 (2)
O3—N2—C3—C232.6 (3)C15—N5—C12—C1180.1 (2)
O3—N2—C3—C4153.8 (2)C17—N5—C12—C11161.83 (19)
O4—N2—C3—C2144.7 (2)N4—C11—C12—N558.9 (3)
O4—N2—C3—C428.9 (3)C12—N5—C13—C14167.65 (17)
C7—N3—C4—C351.0 (3)C15—N5—C13—C1467.8 (2)
C7—N3—C4—C5129.9 (2)C17—N5—C13—C1448.9 (2)
C9—N3—C4—C3164.9 (2)C16—N6—C14—C1349.4 (2)
C9—N3—C4—C514.2 (3)C18—N6—C14—C1367.5 (2)
N2—C3—C4—N36.3 (3)N5—C13—C14—N614.6 (2)
N2—C3—C4—C5172.9 (2)C12—N5—C15—C16176.81 (18)
C2—C3—C4—N3179.3 (2)C13—N5—C15—C1652.6 (2)
C2—C3—C4—C50.1 (3)C17—N5—C15—C1665.3 (2)
N3—C4—C5—C6178.8 (2)C14—N6—C16—C1565.0 (2)
C3—C4—C5—C60.5 (3)C18—N6—C16—C1552.4 (2)
C4—C5—C6—C10.8 (4)N5—C15—C16—N612.1 (3)
N1—C1—C6—C5176.4 (2)C12—N5—C17—C18173.71 (18)
C2—C1—C6—C52.7 (3)C13—N5—C17—C1864.6 (2)
C4—N3—C7—C8156.82 (19)C15—N5—C17—C1852.3 (2)
C9—N3—C7—C856.5 (2)C14—N6—C18—C1751.0 (2)
C10—N4—C8—C762.4 (2)C16—N6—C18—C1766.2 (2)
C11—N4—C8—C7173.35 (18)N5—C17—C18—N612.2 (3)
N3—C7—C8—N460.1 (2)
 

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