1-{2-[4-(2,4-Di­nitro­phenyl)­piperazin-1-yl]ethyl}-4-aza-1-azoniabi­cyclo­[2.2.2]­octane chloride

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.

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

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Computing details

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

Crystal data

C18H27N6O4^+·Cl^−	F(000) = 904
Mr = 426.91	Dx = 1.438 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.9664 (14) Å	Cell parameters from 4679 reflections
b = 24.389 (5) Å	θ = 2.9–27.5°
c = 11.713 (2) Å	µ = 0.23 mm^−1
β = 97.63 (3)°	T = 150 K
V = 1972.4 (7) Å^3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer	3439 independent reflections
Radiation source: sealed tube	2443 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
φ and ω scans	θmax = 25.0°, θmin = 4.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −8→8
Tmin = 0.93, Tmax = 0.96	k = −29→29
25990 measured reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0259P)^2 + 1.2199P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3439 reflections	Δρmax = 0.21 e Å^−3
263 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (7)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.98012 (8)	0.70015 (2)	0.79270 (5)	0.02402 (17)
O1	0.9758 (2)	0.41449 (7)	0.89123 (16)	0.0378 (5)
O2	1.1529 (2)	0.48746 (7)	0.91560 (15)	0.0357 (5)
O3	0.3215 (3)	0.42861 (7)	0.69357 (17)	0.0452 (6)
O4	0.3004 (2)	0.48088 (6)	0.54423 (14)	0.0269 (4)
N1	1.0023 (3)	0.46361 (8)	0.87736 (17)	0.0263 (5)
N2	0.3741 (3)	0.46832 (8)	0.64141 (18)	0.0223 (5)
N3	0.4321 (3)	0.58812 (7)	0.60285 (16)	0.0196 (4)
N4	0.1585 (3)	0.66049 (7)	0.47876 (16)	0.0194 (4)
N5	0.0067 (3)	0.78021 (7)	0.45569 (15)	0.0177 (4)
N6	−0.0598 (3)	0.85057 (7)	0.60961 (16)	0.0232 (5)
C1	0.8486 (3)	0.49533 (9)	0.81036 (19)	0.0202 (5)
C2	0.6771 (3)	0.47010 (9)	0.76672 (19)	0.0207 (5)
H2	0.6539	0.4328	0.7837	0.025*
C3	0.5399 (3)	0.50050 (9)	0.69765 (19)	0.0173 (5)
C4	0.5650 (3)	0.55670 (9)	0.67239 (19)	0.0176 (5)
C5	0.7413 (3)	0.57985 (9)	0.72283 (19)	0.0207 (5)
H5	0.7651	0.6175	0.7091	0.025*
C6	0.8797 (3)	0.55051 (9)	0.79060 (19)	0.0212 (5)
H6	0.9961	0.5678	0.8239	0.025*
C7	0.2273 (3)	0.58943 (9)	0.6227 (2)	0.0194 (5)
H7A	0.2110	0.6160	0.6846	0.023*
H7B	0.1882	0.5528	0.6476	0.023*
C8	0.1009 (3)	0.60579 (9)	0.5138 (2)	0.0211 (6)
H8A	0.1150	0.5789	0.4521	0.025*
H8B	−0.0366	0.6062	0.5270	0.025*
C9	0.4932 (3)	0.64086 (9)	0.5604 (2)	0.0225 (6)
H9A	0.6272	0.6378	0.5417	0.027*
H9B	0.4918	0.6690	0.6211	0.027*
C10	0.3591 (3)	0.65811 (9)	0.4540 (2)	0.0214 (5)
H10A	0.3985	0.6946	0.4282	0.026*
H10B	0.3689	0.6316	0.3910	0.026*
C11	0.0254 (3)	0.68101 (9)	0.3809 (2)	0.0211 (5)
H11A	−0.1089	0.6727	0.3944	0.025*
H11B	0.0499	0.6609	0.3109	0.025*
C12	0.0413 (3)	0.74204 (9)	0.35869 (19)	0.0206 (5)
H12A	0.1724	0.7495	0.3386	0.025*
H12B	−0.0525	0.7514	0.2904	0.025*
C13	−0.1617 (3)	0.76198 (9)	0.5146 (2)	0.0185 (5)
H13A	−0.1263	0.7288	0.5614	0.022*
H13B	−0.2740	0.7530	0.4566	0.022*
C14	−0.2142 (3)	0.80880 (9)	0.5921 (2)	0.0247 (6)
H14A	−0.3360	0.8262	0.5566	0.030*
H14B	−0.2364	0.7937	0.6677	0.030*
C15	0.1812 (3)	0.78547 (9)	0.54612 (19)	0.0213 (6)
H15A	0.2906	0.8019	0.5121	0.026*
H15B	0.2214	0.7489	0.5771	0.026*
C16	0.1252 (3)	0.82251 (9)	0.6434 (2)	0.0230 (6)
H16A	0.1158	0.7999	0.7126	0.028*
H16B	0.2281	0.8502	0.6636	0.028*
C17	−0.0352 (3)	0.83649 (9)	0.4035 (2)	0.0229 (6)
H17A	−0.1586	0.8357	0.3507	0.027*
H17B	0.0695	0.8472	0.3585	0.027*
C18	−0.0491 (4)	0.87833 (9)	0.4999 (2)	0.0277 (6)
H18A	0.0658	0.9026	0.5074	0.033*
H18B	−0.1657	0.9014	0.4800	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0201 (3)	0.0228 (3)	0.0280 (3)	−0.0008 (3)	−0.0013 (2)	−0.0013 (3)
O1	0.0276 (10)	0.0270 (11)	0.0568 (13)	0.0007 (8)	−0.0016 (9)	0.0118 (9)
O2	0.0208 (10)	0.0386 (11)	0.0442 (12)	−0.0032 (8)	−0.0082 (9)	−0.0030 (9)
O3	0.0394 (12)	0.0355 (11)	0.0552 (13)	−0.0219 (9)	−0.0140 (10)	0.0225 (10)
O4	0.0268 (10)	0.0307 (10)	0.0217 (10)	−0.0042 (8)	−0.0019 (8)	−0.0022 (8)
N1	0.0229 (12)	0.0295 (12)	0.0264 (12)	0.0009 (10)	0.0029 (10)	0.0003 (10)
N2	0.0182 (11)	0.0180 (11)	0.0309 (13)	0.0003 (9)	0.0034 (9)	−0.0028 (10)
N3	0.0147 (10)	0.0162 (10)	0.0286 (12)	−0.0013 (8)	0.0053 (9)	0.0034 (9)
N4	0.0142 (10)	0.0198 (10)	0.0241 (11)	−0.0013 (8)	0.0020 (8)	0.0000 (9)
N5	0.0150 (10)	0.0192 (10)	0.0182 (10)	−0.0003 (8)	−0.0001 (8)	0.0010 (8)
N6	0.0204 (11)	0.0207 (11)	0.0279 (12)	0.0012 (9)	0.0015 (9)	0.0001 (9)
C1	0.0181 (13)	0.0247 (13)	0.0175 (13)	0.0014 (10)	0.0017 (10)	−0.0016 (10)
C2	0.0230 (13)	0.0186 (12)	0.0212 (13)	−0.0017 (10)	0.0054 (11)	−0.0003 (11)
C3	0.0149 (12)	0.0179 (12)	0.0196 (13)	−0.0030 (10)	0.0040 (10)	−0.0042 (10)
C4	0.0162 (12)	0.0202 (12)	0.0175 (12)	0.0001 (10)	0.0065 (10)	−0.0029 (10)
C5	0.0210 (13)	0.0199 (12)	0.0221 (13)	−0.0050 (10)	0.0068 (11)	−0.0034 (11)
C6	0.0179 (13)	0.0255 (13)	0.0206 (13)	−0.0053 (10)	0.0031 (10)	−0.0041 (11)
C7	0.0149 (12)	0.0180 (12)	0.0263 (14)	−0.0025 (10)	0.0059 (10)	−0.0016 (10)
C8	0.0155 (13)	0.0205 (13)	0.0282 (14)	−0.0020 (10)	0.0059 (11)	−0.0054 (11)
C9	0.0162 (13)	0.0196 (12)	0.0323 (15)	−0.0014 (10)	0.0054 (11)	0.0020 (11)
C10	0.0188 (13)	0.0187 (12)	0.0274 (14)	−0.0017 (10)	0.0063 (11)	−0.0010 (11)
C11	0.0179 (13)	0.0244 (13)	0.0203 (13)	−0.0004 (10)	0.0000 (10)	−0.0030 (10)
C12	0.0187 (13)	0.0277 (13)	0.0148 (13)	−0.0012 (10)	−0.0001 (10)	−0.0025 (10)
C13	0.0157 (12)	0.0193 (12)	0.0202 (13)	−0.0022 (10)	0.0010 (10)	0.0028 (10)
C14	0.0190 (13)	0.0269 (14)	0.0287 (14)	−0.0002 (11)	0.0052 (11)	−0.0002 (11)
C15	0.0137 (12)	0.0239 (13)	0.0244 (14)	0.0006 (10)	−0.0044 (10)	−0.0014 (11)
C16	0.0198 (13)	0.0210 (12)	0.0267 (14)	−0.0006 (10)	−0.0031 (11)	−0.0034 (11)
C17	0.0225 (13)	0.0199 (13)	0.0256 (14)	−0.0023 (10)	0.0006 (11)	0.0084 (11)
C18	0.0254 (14)	0.0195 (13)	0.0371 (16)	0.0031 (11)	0.0008 (12)	0.0061 (12)

Geometric parameters (Å, º)

O1—N1	1.226 (2)	C7—H7B	0.990
O2—N1	1.231 (2)	C7—C8	1.505 (3)
O3—N2	1.227 (2)	C8—H8A	0.990
O4—N2	1.224 (2)	C8—H8B	0.990
N1—C1	1.462 (3)	C9—H9A	0.990
N2—C3	1.477 (3)	C9—H9B	0.990
N3—C4	1.381 (3)	C9—C10	1.515 (3)
N3—C7	1.476 (3)	C10—H10A	0.990
N3—C9	1.462 (3)	C10—H10B	0.990
N4—C8	1.467 (3)	C11—H11A	0.990
N4—C10	1.466 (3)	C11—H11B	0.990
N4—C11	1.463 (3)	C11—C12	1.518 (3)
N5—C12	1.513 (3)	C12—H12A	0.990
N5—C13	1.505 (3)	C12—H12B	0.990
N5—C15	1.508 (3)	C13—H13A	0.990
N5—C17	1.515 (3)	C13—H13B	0.990
N6—C14	1.475 (3)	C13—C14	1.532 (3)
N6—C16	1.466 (3)	C14—H14A	0.990
N6—C18	1.463 (3)	C14—H14B	0.990
C1—C2	1.380 (3)	C15—H15A	0.990
C1—C6	1.388 (3)	C15—H15B	0.990
C2—H2	0.950	C15—C16	1.544 (3)
C2—C3	1.383 (3)	C16—H16A	0.990
C3—C4	1.418 (3)	C16—H16B	0.990
C4—C5	1.409 (3)	C17—H17A	0.990
C5—H5	0.950	C17—H17B	0.990
C5—C6	1.367 (3)	C17—C18	1.535 (3)
C6—H6	0.950	C18—H18A	0.990
C7—H7A	0.990	C18—H18B	0.990
O1—N1—O2	123.3 (2)	H9B—C9—C10	109.6
O1—N1—C1	118.41 (19)	N4—C10—C9	110.35 (19)
O2—N1—C1	118.3 (2)	N4—C10—H10A	109.6
O3—N2—O4	123.00 (19)	N4—C10—H10B	109.6
O3—N2—C3	117.70 (19)	C9—C10—H10A	109.6
O4—N2—C3	119.23 (19)	C9—C10—H10B	109.6
C4—N3—C7	120.34 (18)	H10A—C10—H10B	108.1
C4—N3—C9	119.10 (18)	N4—C11—H11A	108.6
C7—N3—C9	111.43 (17)	N4—C11—H11B	108.6
C8—N4—C10	108.84 (17)	N4—C11—C12	114.63 (18)
C8—N4—C11	111.18 (17)	H11A—C11—H11B	107.6
C10—N4—C11	112.33 (18)	H11A—C11—C12	108.6
C12—N5—C13	111.98 (17)	H11B—C11—C12	108.6
C12—N5—C15	112.69 (17)	N5—C12—C11	116.89 (19)
C12—N5—C17	107.19 (17)	N5—C12—H12A	108.1
C13—N5—C15	107.93 (17)	N5—C12—H12B	108.1
C13—N5—C17	109.43 (17)	C11—C12—H12A	108.1
C15—N5—C17	107.50 (16)	C11—C12—H12B	108.1
C14—N6—C16	108.27 (17)	H12A—C12—H12B	107.3
C14—N6—C18	108.57 (18)	N5—C13—H13A	110.1
C16—N6—C18	107.88 (19)	N5—C13—H13B	110.1
N1—C1—C2	119.9 (2)	N5—C13—C14	108.23 (17)
N1—C1—C6	118.9 (2)	H13A—C13—H13B	108.4
C2—C1—C6	121.1 (2)	H13A—C13—C14	110.1
C1—C2—H2	120.8	H13B—C13—C14	110.1
C1—C2—C3	118.3 (2)	N6—C14—C13	111.74 (18)
H2—C2—C3	120.8	N6—C14—H14A	109.3
N2—C3—C2	114.52 (19)	N6—C14—H14B	109.3
N2—C3—C4	122.08 (19)	C13—C14—H14A	109.3
C2—C3—C4	123.1 (2)	C13—C14—H14B	109.3
N3—C4—C3	124.6 (2)	H14A—C14—H14B	107.9
N3—C4—C5	120.2 (2)	N5—C15—H15A	110.1
C3—C4—C5	115.1 (2)	N5—C15—H15B	110.1
C4—C5—H5	118.6	N5—C15—C16	107.98 (17)
C4—C5—C6	122.8 (2)	H15A—C15—H15B	108.4
H5—C5—C6	118.6	H15A—C15—C16	110.1
C1—C6—C5	119.4 (2)	H15B—C15—C16	110.1
C1—C6—H6	120.3	N6—C16—C15	111.93 (18)
C5—C6—H6	120.3	N6—C16—H16A	109.2
N3—C7—H7A	109.7	N6—C16—H16B	109.2
N3—C7—H7B	109.7	C15—C16—H16A	109.2
N3—C7—C8	109.99 (19)	C15—C16—H16B	109.2
H7A—C7—H7B	108.2	H16A—C16—H16B	107.9
H7A—C7—C8	109.7	N5—C17—H17A	109.8
H7B—C7—C8	109.7	N5—C17—H17B	109.8
N4—C8—C7	109.07 (18)	N5—C17—C18	109.42 (18)
N4—C8—H8A	109.9	H17A—C17—H17B	108.2
N4—C8—H8B	109.9	H17A—C17—C18	109.8
C7—C8—H8A	109.9	H17B—C17—C18	109.8
C7—C8—H8B	109.9	N6—C18—C17	110.76 (18)
H8A—C8—H8B	108.3	N6—C18—H18A	109.5
N3—C9—H9A	109.6	N6—C18—H18B	109.5
N3—C9—H9B	109.6	C17—C18—H18A	109.5
N3—C9—C10	110.41 (18)	C17—C18—H18B	109.5
H9A—C9—H9B	108.1	H18A—C18—H18B	108.1
H9A—C9—C10	109.6
O1—N1—C1—C2	1.5 (3)	C4—N3—C9—C10	158.45 (19)
O1—N1—C1—C6	−177.7 (2)	C7—N3—C9—C10	−54.5 (2)
O2—N1—C1—C2	−179.6 (2)	C8—N4—C10—C9	−60.8 (2)
O2—N1—C1—C6	1.3 (3)	C11—N4—C10—C9	175.65 (17)
N1—C1—C2—C3	−175.9 (2)	N3—C9—C10—N4	56.8 (2)
C6—C1—C2—C3	3.2 (3)	C8—N4—C11—C12	164.80 (19)
C1—C2—C3—N2	171.60 (19)	C10—N4—C11—C12	−73.0 (2)
C1—C2—C3—C4	−1.9 (3)	C13—N5—C12—C11	−41.8 (2)
O3—N2—C3—C2	32.6 (3)	C15—N5—C12—C11	80.1 (2)
O3—N2—C3—C4	−153.8 (2)	C17—N5—C12—C11	−161.83 (19)
O4—N2—C3—C2	−144.7 (2)	N4—C11—C12—N5	−58.9 (3)
O4—N2—C3—C4	28.9 (3)	C12—N5—C13—C14	−167.65 (17)
C7—N3—C4—C3	51.0 (3)	C15—N5—C13—C14	67.8 (2)
C7—N3—C4—C5	−129.9 (2)	C17—N5—C13—C14	−48.9 (2)
C9—N3—C4—C3	−164.9 (2)	C16—N6—C14—C13	−49.4 (2)
C9—N3—C4—C5	14.2 (3)	C18—N6—C14—C13	67.5 (2)
N2—C3—C4—N3	6.3 (3)	N5—C13—C14—N6	−14.6 (2)
N2—C3—C4—C5	−172.9 (2)	C12—N5—C15—C16	−176.81 (18)
C2—C3—C4—N3	179.3 (2)	C13—N5—C15—C16	−52.6 (2)
C2—C3—C4—C5	0.1 (3)	C17—N5—C15—C16	65.3 (2)
N3—C4—C5—C6	−178.8 (2)	C14—N6—C16—C15	65.0 (2)
C3—C4—C5—C6	0.5 (3)	C18—N6—C16—C15	−52.4 (2)
C4—C5—C6—C1	0.8 (4)	N5—C15—C16—N6	−12.1 (3)
N1—C1—C6—C5	176.4 (2)	C12—N5—C17—C18	−173.71 (18)
C2—C1—C6—C5	−2.7 (3)	C13—N5—C17—C18	64.6 (2)
C4—N3—C7—C8	−156.82 (19)	C15—N5—C17—C18	−52.3 (2)
C9—N3—C7—C8	56.5 (2)	C14—N6—C18—C17	−51.0 (2)
C10—N4—C8—C7	62.4 (2)	C16—N6—C18—C17	66.2 (2)
C11—N4—C8—C7	−173.35 (18)	N5—C17—C18—N6	−12.2 (3)
N3—C7—C8—N4	−60.1 (2)