2-{1-[2-((2-Ammonio­ethyl){2-[1-(5-chloro-2-hydroxy­phen­yl)ethyl­idene­amino]eth­yl}amino)ethyl­iminio]eth­yl}-4-chloro­phenolate trifluoro­acetate

Lee, S.M.; Ali, H.M.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809002943

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o410

doi:10.1107/S1600536809002943

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2-{1-[2-((2-Ammonioethyl){2-[1-(5-chloro-2-hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate trifluoroacetate

See Mun Lee,^a Hapipah Mohd. Ali,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 January 2009; accepted 23 January 2009; online 28 January 2009)

In the title ion-pair, C₂₂H₂₉Cl₂N₄O₂⁺·C₂F₃O₂⁻, ammonium–carboxylate N—H⋯O hydrogen bonds link two cations and two anions about a centre of inversion to generate a hydrogen-bonded tetramer. In the cation, one of the imino N atoms is protonated and donates a hydrogen bond to the O atom of the adjacent chlorophenyl ring. The other imino N atom acts as a hydrogen-bond acceptor from a phenolate O atom.

Related literature

The precursor Schiff base, bis{2-[1-(5-chloro-2-hydroxyphenyl)ethyleneamino]ethyl}{2-[1-(5-chloro-2-phenolate)ethyleneaminio]ethyl}amine, has one of the three C=N double bonds protonated on the N atom (Lee et al., 2009 ).

Experimental

Crystal data

C₂₂H₂₉Cl₂N₄O₂⁺·C₂F₃O₂⁻
M_r = 565.41
Triclinic, $[P \overline 1]$
a = 10.1041 (2) Å
b = 10.6788 (2) Å
c = 12.5241 (3) Å
α = 88.386 (1)°
β = 70.743 (1)°
γ = 81.234 (2)°
V = 1260.48 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 (2) K
0.06 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.994
12201 measured reflections
5762 independent reflections
4104 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.126
S = 1.03
5762 reflections
356 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H21⋯N2	0.85 (1)	1.68 (2)	2.493 (2)	159 (4)
N1—H11⋯O1	0.89 (1)	1.73 (2)	2.520 (2)	147 (3)
N4—H41⋯O1	0.88 (1)	1.88 (1)	2.742 (2)	168 (2)
N4—H42⋯O3	0.89 (1)	1.89 (1)	2.769 (3)	169 (3)
N4—H43⋯O4ⁱ	0.89 (1)	1.92 (2)	2.755 (3)	154 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002943/bt2856sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002943/bt2856Isup2.hkl

checkCIF report

Related literature top

The precursor Schiff base, bis{2-[1-(5-chloro-2-hydroxyphenyl)ethyleneamino]ethyl}{2-[1-(5-chloro-2- phenolate)ethyleneaminio]ethyl}amine, has one of the three C═N double bonds protonated on the N atom (Lee et al., 2009).

Experimental top

Tris(2-aminoethyl)amine (1.46 g m 10 mmol) was condensed with 5-chloro-2-hydroxyacetophenone (5.12 g, 30 mol) in refluxing ethanol (100 ml) to yield the unsolvated Schiff base. The compound (0.64 g, 1 mmol) and trifluoroacetic acid (0.11 g, 1 mmol) were dissolved in a small volume of ethanol. Crystals of the salt separated after several days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

2-{1-[2-((2-Ammonioethyl){2-[1-(5-chloro-2- hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate trifluoroacetate top

Crystal data top

C₂₂H₂₉Cl₂N₄O₂⁺·C₂F₃O₂⁻	Z = 2
M_r = 565.41	F(000) = 588
Triclinic, P1	D_x = 1.490 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1041 (2) Å	Cell parameters from 2402 reflections
b = 10.6788 (2) Å	θ = 2.2–27.8°
c = 12.5241 (3) Å	µ = 0.32 mm⁻¹
α = 88.386 (1)°	T = 100 K
β = 70.743 (1)°	Prism, yellow
γ = 81.234 (2)°	0.06 × 0.04 × 0.02 mm
V = 1260.48 (5) Å³

Data collection top

Bruker SMART APEX diffractometer	5762 independent reflections
Radiation source: fine-focus sealed tube	4104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.981, T_max = 0.994	k = −13→13
12201 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0533P)² + 0.6261P] where P = (F_o² + 2F_c²)/3
5762 reflections	(Δ/σ)_max = 0.001
356 parameters	Δρ_max = 0.72 e Å⁻³
5 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₂H₂₉Cl₂N₄O₂⁺·C₂F₃O₂⁻	γ = 81.234 (2)°
M_r = 565.41	V = 1260.48 (5) Å³
Triclinic, P1	Z = 2
a = 10.1041 (2) Å	Mo Kα radiation
b = 10.6788 (2) Å	µ = 0.32 mm⁻¹
c = 12.5241 (3) Å	T = 100 K
α = 88.386 (1)°	0.06 × 0.04 × 0.02 mm
β = 70.743 (1)°

Data collection top

Bruker SMART APEX diffractometer	5762 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4104 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.994	R_int = 0.032
12201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	5 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.72 e Å⁻³
5762 reflections	Δρ_min = −0.46 e Å⁻³
356 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.10326 (7)	0.47757 (6)	1.36535 (5)	0.03022 (16)
Cl2	0.46582 (7)	0.29988 (6)	1.26264 (5)	0.03337 (17)
O1	0.24624 (17)	0.42151 (15)	0.87521 (13)	0.0261 (4)
O2	0.22931 (18)	−0.00604 (16)	1.01009 (14)	0.0258 (4)
H21	0.278 (4)	0.005 (4)	0.9419 (14)	0.092 (14)*
O3	0.6309 (2)	0.30567 (19)	0.55587 (16)	0.0445 (5)
O4	0.7436 (2)	0.30693 (16)	0.36975 (14)	0.0349 (4)
N1	0.0653 (2)	0.27355 (18)	0.90939 (15)	0.0203 (4)
H11	0.135 (2)	0.316 (2)	0.871 (2)	0.042 (8)*
N2	0.39560 (19)	0.06404 (17)	0.83106 (15)	0.0214 (4)
N3	0.23242 (19)	0.19477 (17)	0.68450 (15)	0.0207 (4)
N4	0.3612 (2)	0.4419 (2)	0.64538 (17)	0.0242 (4)
H41	0.332 (3)	0.425 (2)	0.7177 (10)	0.027 (7)*
H42	0.4511 (14)	0.408 (2)	0.613 (2)	0.044 (8)*
H43	0.353 (3)	0.5260 (10)	0.641 (2)	0.038 (8)*
C1	0.2076 (2)	0.4375 (2)	0.98379 (18)	0.0200 (5)
C2	0.0963 (2)	0.37800 (19)	1.06063 (18)	0.0177 (4)
C3	0.0633 (2)	0.3952 (2)	1.17817 (18)	0.0193 (5)
H3	−0.0113	0.3569	1.2290	0.023*
C4	0.1376 (2)	0.4664 (2)	1.21953 (18)	0.0216 (5)
C5	0.2434 (2)	0.5277 (2)	1.1471 (2)	0.0247 (5)
H5	0.2925	0.5787	1.1773	0.030*
C6	0.2769 (2)	0.5144 (2)	1.0326 (2)	0.0246 (5)
H6	0.3485	0.5578	0.9842	0.030*
C7	0.0240 (2)	0.2942 (2)	1.01801 (18)	0.0179 (4)
C8	−0.0912 (2)	0.2298 (2)	1.09553 (19)	0.0250 (5)
H8A	−0.1262	0.1773	1.0509	0.037*
H8B	−0.1692	0.2938	1.1394	0.037*
H8C	−0.0539	0.1763	1.1471	0.037*
C9	0.0156 (2)	0.1860 (2)	0.84896 (19)	0.0227 (5)
H9A	−0.0893	0.2016	0.8730	0.027*
H9B	0.0458	0.0976	0.8668	0.027*
C10	0.0773 (2)	0.2056 (2)	0.72269 (19)	0.0231 (5)
H10A	0.0499	0.1418	0.6814	0.028*
H10B	0.0368	0.2906	0.7044	0.028*
C11	0.3915 (2)	0.1380 (2)	1.00730 (18)	0.0193 (5)
C12	0.4442 (2)	0.2098 (2)	1.07147 (19)	0.0214 (5)
H12	0.5183	0.2569	1.0342	0.026*
C13	0.3905 (2)	0.2132 (2)	1.18738 (19)	0.0222 (5)
C14	0.2819 (2)	0.1461 (2)	1.24520 (19)	0.0237 (5)
H14	0.2442	0.1503	1.3255	0.028*
C15	0.2300 (2)	0.0732 (2)	1.18385 (19)	0.0224 (5)
H15	0.1565	0.0261	1.2227	0.027*
C16	0.2827 (2)	0.0670 (2)	1.06586 (19)	0.0208 (5)
C17	0.4476 (2)	0.1367 (2)	0.88267 (19)	0.0214 (5)
C18	0.5569 (3)	0.2198 (2)	0.8265 (2)	0.0273 (5)
H18A	0.5891	0.2051	0.7444	0.041*
H18B	0.6377	0.1995	0.8540	0.041*
H18C	0.5152	0.3089	0.8443	0.041*
C19	0.4354 (3)	0.0499 (2)	0.70858 (19)	0.0259 (5)
H19A	0.4932	−0.0341	0.6833	0.031*
H19B	0.4927	0.1159	0.6711	0.031*
C20	0.3015 (2)	0.0623 (2)	0.6765 (2)	0.0247 (5)
H20A	0.3258	0.0295	0.5981	0.030*
H20B	0.2347	0.0104	0.7273	0.030*
C21	0.2872 (3)	0.2563 (2)	0.57570 (19)	0.0266 (5)
H21A	0.2368	0.2340	0.5249	0.032*
H21B	0.3889	0.2223	0.5404	0.032*
C22	0.2712 (3)	0.3986 (2)	0.5850 (2)	0.0274 (5)
H22A	0.2968	0.4336	0.5081	0.033*
H22B	0.1706	0.4325	0.6256	0.033*
C23	0.7267 (2)	0.2710 (2)	0.4670 (2)	0.0245 (5)
C24	0.8459 (3)	0.1700 (2)	0.4815 (2)	0.0281 (5)
F1	0.79561 (19)	0.07794 (17)	0.54812 (16)	0.0644 (6)
F2	0.9303 (2)	0.21998 (18)	0.5210 (2)	0.0813 (8)
F3	0.92729 (18)	0.11073 (17)	0.38502 (15)	0.0550 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0342 (3)	0.0384 (4)	0.0199 (3)	0.0023 (3)	−0.0144 (3)	−0.0062 (2)
Cl2	0.0386 (4)	0.0377 (4)	0.0288 (3)	−0.0110 (3)	−0.0150 (3)	−0.0050 (3)
O1	0.0300 (9)	0.0305 (9)	0.0170 (8)	−0.0130 (7)	−0.0031 (7)	0.0024 (7)
O2	0.0267 (9)	0.0292 (9)	0.0234 (9)	−0.0125 (7)	−0.0069 (8)	0.0015 (7)
O3	0.0322 (10)	0.0547 (13)	0.0297 (10)	0.0114 (9)	0.0037 (8)	0.0106 (9)
O4	0.0475 (11)	0.0331 (10)	0.0223 (9)	−0.0028 (8)	−0.0111 (8)	0.0062 (7)
N1	0.0228 (10)	0.0221 (10)	0.0169 (9)	−0.0087 (8)	−0.0054 (8)	−0.0002 (7)
N2	0.0216 (10)	0.0239 (10)	0.0186 (9)	−0.0002 (8)	−0.0078 (8)	0.0011 (8)
N3	0.0235 (10)	0.0230 (10)	0.0149 (9)	−0.0012 (8)	−0.0065 (8)	−0.0002 (7)
N4	0.0251 (11)	0.0292 (12)	0.0153 (10)	−0.0029 (9)	−0.0034 (9)	0.0054 (8)
C1	0.0233 (11)	0.0173 (11)	0.0197 (11)	−0.0029 (9)	−0.0076 (9)	0.0027 (8)
C2	0.0183 (11)	0.0156 (10)	0.0199 (11)	−0.0020 (8)	−0.0075 (9)	0.0006 (8)
C3	0.0202 (11)	0.0190 (11)	0.0165 (11)	0.0015 (9)	−0.0050 (9)	0.0007 (8)
C4	0.0269 (12)	0.0216 (11)	0.0174 (11)	0.0016 (9)	−0.0110 (10)	−0.0022 (9)
C5	0.0286 (12)	0.0202 (12)	0.0312 (13)	−0.0046 (9)	−0.0170 (11)	−0.0014 (9)
C6	0.0268 (12)	0.0207 (12)	0.0282 (13)	−0.0095 (9)	−0.0094 (10)	0.0035 (9)
C7	0.0191 (11)	0.0159 (10)	0.0186 (11)	−0.0005 (8)	−0.0071 (9)	0.0003 (8)
C8	0.0282 (12)	0.0281 (13)	0.0196 (11)	−0.0121 (10)	−0.0058 (10)	0.0021 (9)
C9	0.0248 (12)	0.0242 (12)	0.0215 (11)	−0.0074 (9)	−0.0088 (10)	−0.0031 (9)
C10	0.0271 (12)	0.0241 (12)	0.0203 (11)	−0.0028 (9)	−0.0110 (10)	−0.0021 (9)
C11	0.0205 (11)	0.0179 (11)	0.0191 (11)	−0.0013 (9)	−0.0067 (9)	0.0018 (8)
C12	0.0200 (11)	0.0190 (11)	0.0255 (12)	−0.0039 (9)	−0.0075 (10)	0.0032 (9)
C13	0.0236 (12)	0.0211 (12)	0.0237 (12)	−0.0011 (9)	−0.0108 (10)	−0.0017 (9)
C14	0.0245 (12)	0.0256 (12)	0.0179 (11)	0.0009 (9)	−0.0050 (9)	0.0011 (9)
C15	0.0200 (11)	0.0212 (11)	0.0231 (12)	−0.0034 (9)	−0.0033 (9)	0.0034 (9)
C16	0.0179 (11)	0.0207 (11)	0.0234 (12)	−0.0015 (9)	−0.0069 (9)	0.0012 (9)
C17	0.0192 (11)	0.0199 (11)	0.0251 (12)	−0.0013 (9)	−0.0083 (10)	0.0029 (9)
C18	0.0277 (13)	0.0311 (13)	0.0216 (12)	−0.0091 (10)	−0.0046 (10)	0.0049 (10)
C19	0.0283 (13)	0.0291 (13)	0.0182 (11)	0.0023 (10)	−0.0075 (10)	−0.0010 (9)
C20	0.0302 (13)	0.0238 (12)	0.0209 (12)	−0.0009 (10)	−0.0106 (10)	−0.0035 (9)
C21	0.0310 (13)	0.0331 (13)	0.0150 (11)	−0.0018 (10)	−0.0078 (10)	0.0008 (9)
C22	0.0313 (13)	0.0306 (13)	0.0209 (12)	−0.0048 (10)	−0.0097 (10)	0.0075 (10)
C23	0.0244 (12)	0.0243 (12)	0.0239 (12)	−0.0046 (9)	−0.0069 (10)	0.0038 (9)
C24	0.0271 (13)	0.0301 (13)	0.0257 (13)	−0.0042 (10)	−0.0072 (11)	0.0029 (10)
F1	0.0543 (11)	0.0495 (11)	0.0659 (13)	0.0096 (9)	0.0014 (10)	0.0328 (10)
F2	0.0898 (15)	0.0505 (12)	0.143 (2)	0.0103 (10)	−0.0980 (16)	−0.0211 (12)
F3	0.0445 (10)	0.0601 (12)	0.0440 (10)	0.0166 (8)	−0.0026 (8)	−0.0095 (8)

Geometric parameters (Å, º) top

Cl1—C4	1.747 (2)	C9—C10	1.518 (3)
Cl2—C13	1.749 (2)	C9—H9A	0.9900
O1—C1	1.294 (3)	C9—H9B	0.9900
O2—C16	1.339 (3)	C10—H10A	0.9900
O2—H21	0.847 (10)	C10—H10B	0.9900
O3—C23	1.231 (3)	C11—C12	1.400 (3)
O4—C23	1.231 (3)	C11—C16	1.419 (3)
N1—C7	1.299 (3)	C11—C17	1.474 (3)
N1—C9	1.460 (3)	C12—C13	1.371 (3)
N1—H11	0.889 (10)	C12—H12	0.9500
N2—C17	1.293 (3)	C13—C14	1.389 (3)
N2—C19	1.458 (3)	C14—C15	1.377 (3)
N3—C10	1.467 (3)	C14—H14	0.9500
N3—C20	1.469 (3)	C15—C16	1.396 (3)
N3—C21	1.469 (3)	C15—H15	0.9500
N4—C22	1.487 (3)	C17—C18	1.501 (3)
N4—H41	0.878 (10)	C18—H18A	0.9800
N4—H42	0.886 (10)	C18—H18B	0.9800
N4—H43	0.892 (10)	C18—H18C	0.9800
C1—C6	1.423 (3)	C19—C20	1.520 (3)
C1—C2	1.436 (3)	C19—H19A	0.9900
C2—C3	1.409 (3)	C19—H19B	0.9900
C2—C7	1.450 (3)	C20—H20A	0.9900
C3—C4	1.365 (3)	C20—H20B	0.9900
C3—H3	0.9500	C21—C22	1.507 (3)
C4—C5	1.391 (3)	C21—H21A	0.9900
C5—C6	1.367 (3)	C21—H21B	0.9900
C5—H5	0.9500	C22—H22A	0.9900
C6—H6	0.9500	C22—H22B	0.9900
C7—C8	1.494 (3)	C23—C24	1.545 (3)
C8—H8A	0.9800	C24—F2	1.299 (3)
C8—H8B	0.9800	C24—F1	1.322 (3)
C8—H8C	0.9800	C24—F3	1.329 (3)

C16—O2—H21	102 (3)	C13—C12—H12	119.5
C7—N1—C9	127.14 (19)	C11—C12—H12	119.5
C7—N1—H11	113.5 (19)	C12—C13—C14	121.3 (2)
C9—N1—H11	119.3 (19)	C12—C13—Cl2	118.69 (18)
C17—N2—C19	124.9 (2)	C14—C13—Cl2	119.96 (18)
C10—N3—C20	112.17 (18)	C15—C14—C13	118.7 (2)
C10—N3—C21	111.60 (18)	C15—C14—H14	120.7
C20—N3—C21	109.93 (18)	C13—C14—H14	120.7
C22—N4—H41	112.4 (17)	C14—C15—C16	121.5 (2)
C22—N4—H42	110.4 (19)	C14—C15—H15	119.2
H41—N4—H42	110 (3)	C16—C15—H15	119.2
C22—N4—H43	107.7 (18)	O2—C16—C15	119.2 (2)
H41—N4—H43	106 (2)	O2—C16—C11	121.3 (2)
H42—N4—H43	109 (3)	C15—C16—C11	119.5 (2)
O1—C1—C6	120.6 (2)	N2—C17—C11	116.1 (2)
O1—C1—C2	122.6 (2)	N2—C17—C18	125.6 (2)
C6—C1—C2	116.8 (2)	C11—C17—C18	118.3 (2)
C3—C2—C1	119.7 (2)	C17—C18—H18A	109.5
C3—C2—C7	119.8 (2)	C17—C18—H18B	109.5
C1—C2—C7	120.32 (19)	H18A—C18—H18B	109.5
C4—C3—C2	120.5 (2)	C17—C18—H18C	109.5
C4—C3—H3	119.8	H18A—C18—H18C	109.5
C2—C3—H3	119.8	H18B—C18—H18C	109.5
C3—C4—C5	121.0 (2)	N2—C19—C20	108.94 (19)
C3—C4—Cl1	119.76 (18)	N2—C19—H19A	109.9
C5—C4—Cl1	119.19 (17)	C20—C19—H19A	109.9
C6—C5—C4	120.0 (2)	N2—C19—H19B	109.9
C6—C5—H5	120.0	C20—C19—H19B	109.9
C4—C5—H5	120.0	H19A—C19—H19B	108.3
C5—C6—C1	121.9 (2)	N3—C20—C19	111.49 (19)
C5—C6—H6	119.0	N3—C20—H20A	109.3
C1—C6—H6	119.0	C19—C20—H20A	109.3
N1—C7—C2	117.78 (19)	N3—C20—H20B	109.3
N1—C7—C8	120.4 (2)	C19—C20—H20B	109.3
C2—C7—C8	121.75 (19)	H20A—C20—H20B	108.0
C7—C8—H8A	109.5	N3—C21—C22	114.00 (19)
C7—C8—H8B	109.5	N3—C21—H21A	108.8
H8A—C8—H8B	109.5	C22—C21—H21A	108.8
C7—C8—H8C	109.5	N3—C21—H21B	108.8
H8A—C8—H8C	109.5	C22—C21—H21B	108.8
H8B—C8—H8C	109.5	H21A—C21—H21B	107.6
N1—C9—C10	109.14 (18)	N4—C22—C21	112.88 (19)
N1—C9—H9A	109.9	N4—C22—H22A	109.0
C10—C9—H9A	109.9	C21—C22—H22A	109.0
N1—C9—H9B	109.9	N4—C22—H22B	109.0
C10—C9—H9B	109.9	C21—C22—H22B	109.0
H9A—C9—H9B	108.3	H22A—C22—H22B	107.8
N3—C10—C9	112.01 (18)	O3—C23—O4	130.0 (2)
N3—C10—H10A	109.2	O3—C23—C24	114.3 (2)
C9—C10—H10A	109.2	O4—C23—C24	115.6 (2)
N3—C10—H10B	109.2	F2—C24—F1	109.2 (2)
C9—C10—H10B	109.2	F2—C24—F3	106.2 (2)
H10A—C10—H10B	107.9	F1—C24—F3	104.2 (2)
C12—C11—C16	118.0 (2)	F2—C24—C23	111.5 (2)
C12—C11—C17	120.8 (2)	F1—C24—C23	112.3 (2)
C16—C11—C17	121.2 (2)	F3—C24—C23	113.1 (2)
C13—C12—C11	121.0 (2)

O1—C1—C2—C3	177.41 (19)	Cl2—C13—C14—C15	−176.52 (17)
C6—C1—C2—C3	−1.5 (3)	C13—C14—C15—C16	−0.8 (3)
O1—C1—C2—C7	1.2 (3)	C14—C15—C16—O2	179.5 (2)
C6—C1—C2—C7	−177.62 (19)	C14—C15—C16—C11	−0.6 (3)
C1—C2—C3—C4	−1.0 (3)	C12—C11—C16—O2	−178.6 (2)
C7—C2—C3—C4	175.23 (19)	C17—C11—C16—O2	1.6 (3)
C2—C3—C4—C5	2.6 (3)	C12—C11—C16—C15	1.5 (3)
C2—C3—C4—Cl1	−175.57 (16)	C17—C11—C16—C15	−178.3 (2)
C3—C4—C5—C6	−1.7 (3)	C19—N2—C17—C11	179.43 (19)
Cl1—C4—C5—C6	176.49 (18)	C19—N2—C17—C18	0.4 (4)
C4—C5—C6—C1	−0.9 (4)	C12—C11—C17—N2	177.7 (2)
O1—C1—C6—C5	−176.5 (2)	C16—C11—C17—N2	−2.5 (3)
C2—C1—C6—C5	2.4 (3)	C12—C11—C17—C18	−3.2 (3)
C9—N1—C7—C2	175.0 (2)	C16—C11—C17—C18	176.6 (2)
C9—N1—C7—C8	−3.1 (3)	C17—N2—C19—C20	−131.8 (2)
C3—C2—C7—N1	−174.86 (19)	C10—N3—C20—C19	−145.03 (19)
C1—C2—C7—N1	1.3 (3)	C21—N3—C20—C19	90.2 (2)
C3—C2—C7—C8	3.3 (3)	N2—C19—C20—N3	74.7 (2)
C1—C2—C7—C8	179.4 (2)	C10—N3—C21—C22	78.2 (2)
C7—N1—C9—C10	172.3 (2)	C20—N3—C21—C22	−156.73 (19)
C20—N3—C10—C9	76.3 (2)	N3—C21—C22—N4	67.2 (3)
C21—N3—C10—C9	−159.79 (18)	O3—C23—C24—F2	−76.8 (3)
N1—C9—C10—N3	54.4 (2)	O4—C23—C24—F2	101.3 (3)
C16—C11—C12—C13	−1.1 (3)	O3—C23—C24—F1	46.1 (3)
C17—C11—C12—C13	178.72 (19)	O4—C23—C24—F1	−135.8 (2)
C11—C12—C13—C14	−0.2 (3)	O3—C23—C24—F3	163.6 (2)
C11—C12—C13—Cl2	177.53 (17)	O4—C23—C24—F3	−18.3 (3)
C12—C13—C14—C15	1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···N2	0.85 (1)	1.68 (2)	2.493 (2)	159 (4)
N1—H11···O1	0.89 (1)	1.73 (2)	2.520 (2)	147 (3)
N4—H41···O1	0.88 (1)	1.88 (1)	2.742 (2)	168 (2)
N4—H42···O3	0.89 (1)	1.89 (1)	2.769 (3)	169 (3)
N4—H43···O4ⁱ	0.89 (1)	1.92 (2)	2.755 (3)	154 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₉Cl₂N₄O₂⁺·C₂F₃O₂⁻
M_r	565.41
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.1041 (2), 10.6788 (2), 12.5241 (3)
α, β, γ (°)	88.386 (1), 70.743 (1), 81.234 (2)
V (Å³)	1260.48 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.06 × 0.04 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	12201, 5762, 4104
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.03
No. of reflections	5762
No. of parameters	356
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.46

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···N2	0.85 (1)	1.68 (2)	2.493 (2)	159 (4)
N1—H11···O1	0.89 (1)	1.73 (2)	2.520 (2)	147 (3)
N4—H41···O1	0.88 (1)	1.88 (1)	2.742 (2)	168 (2)
N4—H42···O3	0.89 (1)	1.89 (1)	2.769 (3)	169 (3)
N4—H43···O4ⁱ	0.89 (1)	1.92 (2)	2.755 (3)	154 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank the University of Malaya (grant Nos. FS339/2008A and PS072/2007C) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lee, S. M., Ali, H. M., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o409. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{1-[2-((2-Ammonio­ethyl){2-[1-(5-chloro-2-hy­droxy­phen­yl)ethyl­­idene­amino]eth­yl}amino)ethyl­iminio]eth­yl}-4-chloro­phenolate tri­fluoro­acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{1-[2-((2-Ammonioethyl){2-[1-(5-chloro-2-hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate trifluoroacetate