2-{1-[2-(Bis{2-[1-(5-chloro-2-hydroxy­phen­yl)ethyl­ideneamino]eth­yl}amino)­ethyl­iminio]eth­yl}-4-chloro­phenolate toluene hemisolvate

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

doi:10.1107/S1600536809002906

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o409

doi:10.1107/S1600536809002906

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2-{1-[2-(Bis{2-[1-(5-chloro-2-hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate toluene hemisolvate

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 toluene hemisolvated tripodal tris(2-aminoethyl)amine Schiff base, C₃₀H₃₃Cl₃N₄O₃·0.5C₇H₈, one of the three imino N atoms is protonated, forming a hydrogen bond with the O atom at an adjacent benzene ring. The other two imino N atoms act as hydrogen-bond acceptors from phenolate OH groups. The toluene solvent molecule is disordered about a centre of inversion.

Related literature

For the unsolvated tris{2-[(5-chlorosalicylidene)amino]ethyl}amine, which is refined as a neutral molecule, see: Kanesato et al. (2000 ).

Experimental

Crystal data

C₃₀H₃₃Cl₃N₄O₃·0.5C₇H₈
M_r = 650.02
Triclinic, $[P \overline 1]$
a = 7.3651 (2) Å
b = 11.1839 (2) Å
c = 20.1594 (5) Å
α = 100.618 (2)°
β = 97.765 (2)°
γ = 98.560 (2)°
V = 1591.20 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 100 (2) K
0.22 × 0.18 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.931, T_max = 0.993
14959 measured reflections
7269 independent reflections
4901 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.150
S = 1.04
7269 reflections
410 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.85 (1)	1.69 (2)	2.486 (3)	155 (5)
O2—H2O⋯N2	0.85 (1)	1.70 (2)	2.507 (3)	158 (4)
N3—H3N⋯O3	0.89 (1)	1.62 (2)	2.474 (3)	158 (5)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002906/bt2855sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002906/bt2855Isup2.hkl

checkCIF report

Related literature top

For the unsolvated tris{2-[(5-chlorosalicylidene)amino]ethyl}amine, which is refined as a neutral molecule, see: Kanesato et al. (2000).

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 Schiff base. The solvent was removed and the product recrystallized from toluene.

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: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement plot (Barbour, 2001) of C₃₀H₃₃Cl₃N₄O₃^.0.5C₇H₈ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-{1-[2-(Bis{2-[1-(5-chloro-2- hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate toluene hemisolvate top

Crystal data top

C₃₀H₃₃Cl₃N₄O₃·0.5C₇H₈	Z = 2
M_r = 650.02	F(000) = 682
Triclinic, P1	D_x = 1.357 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3651 (2) Å	Cell parameters from 3243 reflections
b = 11.1839 (2) Å	θ = 2.3–29.3°
c = 20.1594 (5) Å	µ = 0.33 mm⁻¹
α = 100.618 (2)°	T = 100 K
β = 97.765 (2)°	Plate, yellow
γ = 98.560 (2)°	0.22 × 0.18 × 0.02 mm
V = 1591.20 (7) Å³

Data collection top

Bruker SMART APEX diffractometer	7269 independent reflections
Radiation source: fine-focus sealed tube	4901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.931, T_max = 0.993	k = −14→14
14959 measured reflections	l = −26→25

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0807P)² + 0.0533P] where P = (F_o² + 2F_c²)/3
7269 reflections	(Δ/σ)_max = 0.001
410 parameters	Δρ_max = 0.79 e Å⁻³
30 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₃₀H₃₃Cl₃N₄O₃·0.5C₇H₈	γ = 98.560 (2)°
M_r = 650.02	V = 1591.20 (7) Å³
Triclinic, P1	Z = 2
a = 7.3651 (2) Å	Mo Kα radiation
b = 11.1839 (2) Å	µ = 0.33 mm⁻¹
c = 20.1594 (5) Å	T = 100 K
α = 100.618 (2)°	0.22 × 0.18 × 0.02 mm
β = 97.765 (2)°

Data collection top

Bruker SMART APEX diffractometer	7269 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4901 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.993	R_int = 0.033
14959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	30 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.79 e Å⁻³
7269 reflections	Δρ_min = −0.80 e Å⁻³
410 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	−0.23379 (11)	0.63575 (6)	0.19284 (4)	0.03291 (19)
Cl2	0.23675 (10)	0.10135 (7)	0.68824 (3)	0.03301 (19)
Cl3	0.21656 (11)	0.59383 (6)	0.09250 (5)	0.0398 (2)
O1	0.0640 (3)	0.21520 (18)	0.27035 (9)	0.0250 (4)
O2	0.1122 (3)	−0.23059 (17)	0.41888 (9)	0.0268 (4)
O3	0.4300 (2)	0.11432 (15)	0.00308 (9)	0.0209 (4)
N1	0.0135 (3)	0.11221 (18)	0.14742 (10)	0.0173 (4)
N2	0.2570 (3)	−0.05363 (19)	0.37189 (10)	0.0203 (5)
N3	0.5052 (3)	0.0992 (2)	0.12427 (11)	0.0194 (4)
N4	0.2407 (3)	−0.07266 (19)	0.18467 (10)	0.0185 (4)
C1	0.0036 (3)	0.3111 (2)	0.25116 (13)	0.0202 (5)
C2	−0.0030 (4)	0.4161 (3)	0.30111 (13)	0.0263 (6)
H2	0.0400	0.4174	0.3479	0.032*
C3	−0.0698 (4)	0.5162 (2)	0.28386 (14)	0.0267 (6)
H3	−0.0713	0.5867	0.3182	0.032*
C4	−0.1358 (4)	0.5134 (2)	0.21528 (13)	0.0229 (6)
C5	−0.1268 (3)	0.4145 (2)	0.16472 (13)	0.0196 (5)
H5	−0.1684	0.4160	0.1182	0.024*
C6	−0.0570 (3)	0.3114 (2)	0.18097 (12)	0.0172 (5)
C7	−0.0454 (3)	0.2053 (2)	0.12730 (12)	0.0159 (5)
C8	−0.1005 (3)	0.2054 (2)	0.05297 (12)	0.0199 (5)
H8A	0.0064	0.1964	0.0295	0.030*
H8B	−0.1410	0.2834	0.0483	0.030*
H8C	−0.2028	0.1363	0.0325	0.030*
C9	0.0297 (3)	0.0003 (2)	0.09993 (13)	0.0185 (5)
H9A	0.1345	0.0184	0.0752	0.022*
H9B	−0.0860	−0.0278	0.0658	0.022*
C10	0.0625 (3)	−0.1009 (2)	0.13845 (13)	0.0190 (5)
H10A	−0.0391	−0.1145	0.1652	0.023*
H10B	0.0573	−0.1787	0.1050	0.023*
C11	0.1462 (3)	−0.1520 (2)	0.47997 (13)	0.0210 (5)
C12	0.0918 (4)	−0.1964 (3)	0.53595 (13)	0.0247 (6)
H12	0.0335	−0.2803	0.5298	0.030*
C13	0.1212 (4)	−0.1205 (3)	0.60011 (13)	0.0260 (6)
H13	0.0837	−0.1516	0.6379	0.031*
C14	0.2062 (3)	0.0015 (3)	0.60846 (13)	0.0238 (6)
C15	0.2619 (3)	0.0482 (2)	0.55447 (13)	0.0215 (5)
H15	0.3199	0.1323	0.5617	0.026*
C16	0.2337 (3)	−0.0273 (2)	0.48890 (12)	0.0188 (5)
C17	0.2881 (3)	0.0227 (2)	0.43020 (12)	0.0193 (5)
C18	0.3728 (4)	0.1565 (2)	0.43895 (14)	0.0266 (6)
H18A	0.3127	0.1905	0.4020	0.040*
H18B	0.5064	0.1639	0.4374	0.040*
H18C	0.3546	0.2025	0.4832	0.040*
C19	0.2943 (4)	−0.0111 (2)	0.30971 (12)	0.0241 (6)
H19A	0.4289	0.0214	0.3141	0.029*
H19B	0.2253	0.0566	0.3034	0.029*
C20	0.2347 (4)	−0.1166 (3)	0.24873 (13)	0.0256 (6)
H20A	0.3182	−0.1778	0.2515	0.031*
H20B	0.1065	−0.1581	0.2491	0.031*
C21	0.3929 (3)	0.2251 (2)	0.02511 (13)	0.0191 (5)
C22	0.3371 (3)	0.2955 (2)	−0.02214 (14)	0.0221 (5)
H22	0.3345	0.2646	−0.0695	0.027*
C23	0.2860 (4)	0.4080 (2)	−0.00169 (15)	0.0258 (6)
H23	0.2471	0.4539	−0.0346	0.031*
C24	0.2918 (4)	0.4542 (2)	0.06778 (15)	0.0251 (6)
C25	0.3537 (3)	0.3918 (2)	0.11611 (14)	0.0238 (6)
H25	0.3616	0.4269	0.1633	0.029*
C26	0.4060 (3)	0.2759 (2)	0.09650 (13)	0.0190 (5)
C27	0.4692 (3)	0.2072 (2)	0.14771 (13)	0.0203 (5)
C28	0.4898 (4)	0.2621 (3)	0.22289 (13)	0.0263 (6)
H28A	0.5594	0.2133	0.2493	0.040*
H28B	0.3662	0.2612	0.2359	0.040*
H28C	0.5572	0.3474	0.2324	0.040*
C29	0.5577 (3)	0.0091 (2)	0.16366 (14)	0.0249 (6)
H29A	0.5869	0.0481	0.2130	0.030*
H29B	0.6703	−0.0197	0.1498	0.030*
C30	0.3992 (3)	−0.1001 (2)	0.15147 (13)	0.0197 (5)
H30A	0.3555	−0.1282	0.1016	0.024*
H30B	0.4468	−0.1689	0.1685	0.024*
C31	0.4925 (19)	0.5285 (12)	0.4490 (5)	0.083 (3)	0.50
C32	0.3426 (19)	0.5415 (12)	0.4832 (5)	0.059 (3)	0.50
H32	0.2419	0.5754	0.4641	0.071*	0.50
C33	0.340 (2)	0.5050 (13)	0.5454 (5)	0.089 (3)	0.50
H33	0.2376	0.5139	0.5688	0.107*	0.50
C34	0.487 (2)	0.4554 (12)	0.5734 (5)	0.083 (3)	0.50
H34	0.4856	0.4305	0.6159	0.100*	0.50
C35	0.637 (2)	0.4424 (12)	0.5392 (5)	0.059 (3)	0.50
H35	0.7379	0.4085	0.5584	0.071*	0.50
C36	0.6399 (19)	0.4789 (12)	0.4770 (5)	0.089 (3)	0.50
H36	0.7423	0.4700	0.4537	0.107*	0.50
C37	0.5056 (18)	0.5705 (11)	0.3829 (5)	0.123 (5)	0.50
H37A	0.4289	0.6342	0.3792	0.185*	0.50
H37B	0.4608	0.5000	0.3444	0.185*	0.50
H37C	0.6355	0.6046	0.3820	0.185*	0.50
H1O	0.055 (7)	0.163 (4)	0.2335 (15)	0.109 (19)*
H2O	0.150 (5)	−0.183 (3)	0.3934 (17)	0.070 (13)*
H3N	0.484 (7)	0.086 (5)	0.0787 (6)	0.106 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0467 (4)	0.0175 (3)	0.0363 (4)	0.0104 (3)	0.0104 (3)	0.0038 (3)
Cl2	0.0319 (4)	0.0504 (4)	0.0164 (3)	0.0158 (3)	0.0031 (3)	0.0000 (3)
Cl3	0.0402 (4)	0.0188 (3)	0.0650 (5)	0.0116 (3)	0.0178 (4)	0.0090 (3)
O1	0.0271 (10)	0.0307 (10)	0.0202 (10)	0.0102 (8)	0.0048 (8)	0.0083 (8)
O2	0.0335 (11)	0.0250 (10)	0.0218 (10)	0.0038 (9)	0.0068 (8)	0.0040 (8)
O3	0.0219 (9)	0.0183 (8)	0.0240 (9)	0.0072 (7)	0.0046 (7)	0.0047 (7)
N1	0.0129 (10)	0.0182 (10)	0.0211 (11)	0.0020 (8)	0.0049 (8)	0.0042 (8)
N2	0.0199 (11)	0.0250 (11)	0.0180 (11)	0.0057 (9)	0.0054 (8)	0.0066 (9)
N3	0.0152 (10)	0.0222 (11)	0.0229 (12)	0.0020 (8)	0.0034 (9)	0.0106 (9)
N4	0.0176 (10)	0.0238 (11)	0.0159 (10)	0.0042 (9)	0.0049 (8)	0.0073 (8)
C1	0.0168 (12)	0.0246 (13)	0.0192 (12)	0.0012 (10)	0.0055 (10)	0.0044 (10)
C2	0.0269 (14)	0.0314 (14)	0.0178 (13)	0.0006 (12)	0.0041 (11)	0.0010 (11)
C3	0.0286 (14)	0.0230 (13)	0.0242 (14)	0.0005 (11)	0.0067 (11)	−0.0043 (11)
C4	0.0230 (13)	0.0178 (12)	0.0278 (14)	0.0010 (10)	0.0072 (11)	0.0040 (11)
C5	0.0197 (12)	0.0185 (12)	0.0202 (13)	0.0009 (10)	0.0037 (10)	0.0050 (10)
C6	0.0143 (11)	0.0195 (12)	0.0181 (12)	0.0005 (10)	0.0043 (9)	0.0051 (10)
C7	0.0112 (11)	0.0184 (12)	0.0185 (12)	0.0013 (9)	0.0045 (9)	0.0045 (10)
C8	0.0213 (13)	0.0206 (12)	0.0194 (12)	0.0061 (10)	0.0051 (10)	0.0053 (10)
C9	0.0155 (12)	0.0184 (12)	0.0217 (13)	0.0042 (10)	0.0030 (10)	0.0037 (10)
C10	0.0134 (11)	0.0209 (12)	0.0233 (13)	0.0023 (10)	0.0043 (10)	0.0060 (10)
C11	0.0191 (12)	0.0276 (13)	0.0184 (13)	0.0084 (11)	0.0043 (10)	0.0058 (10)
C12	0.0204 (13)	0.0308 (14)	0.0264 (14)	0.0083 (11)	0.0045 (11)	0.0115 (12)
C13	0.0217 (13)	0.0415 (16)	0.0207 (13)	0.0128 (12)	0.0078 (11)	0.0126 (12)
C14	0.0189 (13)	0.0384 (15)	0.0149 (12)	0.0127 (12)	0.0015 (10)	0.0020 (11)
C15	0.0177 (12)	0.0250 (13)	0.0223 (13)	0.0089 (11)	0.0006 (10)	0.0042 (11)
C16	0.0132 (12)	0.0255 (13)	0.0190 (12)	0.0074 (10)	0.0023 (9)	0.0051 (10)
C17	0.0135 (11)	0.0257 (13)	0.0200 (13)	0.0071 (10)	0.0024 (10)	0.0055 (10)
C18	0.0282 (14)	0.0257 (14)	0.0253 (14)	0.0020 (12)	0.0060 (11)	0.0048 (11)
C19	0.0276 (14)	0.0272 (14)	0.0189 (13)	0.0047 (11)	0.0072 (11)	0.0066 (11)
C20	0.0301 (15)	0.0285 (14)	0.0197 (13)	0.0024 (12)	0.0073 (11)	0.0091 (11)
C21	0.0115 (11)	0.0171 (12)	0.0299 (14)	0.0016 (9)	0.0054 (10)	0.0072 (10)
C22	0.0179 (12)	0.0243 (13)	0.0259 (14)	0.0033 (10)	0.0057 (10)	0.0082 (11)
C23	0.0179 (13)	0.0220 (13)	0.0413 (16)	0.0020 (10)	0.0072 (12)	0.0158 (12)
C24	0.0203 (13)	0.0141 (12)	0.0424 (16)	0.0022 (10)	0.0106 (12)	0.0062 (11)
C25	0.0177 (13)	0.0195 (12)	0.0320 (15)	−0.0008 (10)	0.0073 (11)	0.0012 (11)
C26	0.0134 (11)	0.0192 (12)	0.0240 (13)	−0.0009 (10)	0.0043 (10)	0.0053 (10)
C27	0.0118 (11)	0.0233 (13)	0.0246 (13)	−0.0031 (10)	0.0051 (10)	0.0051 (11)
C28	0.0243 (14)	0.0301 (14)	0.0234 (14)	−0.0007 (12)	0.0069 (11)	0.0050 (11)
C29	0.0160 (12)	0.0314 (14)	0.0315 (15)	0.0048 (11)	0.0032 (11)	0.0172 (12)
C30	0.0166 (12)	0.0226 (12)	0.0241 (13)	0.0080 (10)	0.0057 (10)	0.0102 (10)
C31	0.112 (5)	0.036 (4)	0.081 (7)	0.007 (3)	−0.021 (5)	−0.009 (4)
C32	0.058 (3)	0.036 (3)	0.072 (6)	0.019 (3)	−0.013 (4)	−0.008 (4)
C33	0.090 (4)	0.050 (4)	0.109 (7)	0.023 (3)	−0.030 (5)	−0.009 (5)
C34	0.112 (5)	0.036 (4)	0.081 (7)	0.007 (3)	−0.021 (5)	−0.009 (4)
C35	0.058 (3)	0.036 (3)	0.072 (6)	0.019 (3)	−0.013 (4)	−0.008 (4)
C36	0.090 (4)	0.050 (4)	0.109 (7)	0.023 (3)	−0.030 (5)	−0.009 (5)
C37	0.142 (8)	0.097 (7)	0.118 (8)	−0.017 (6)	0.060 (7)	−0.009 (6)

Geometric parameters (Å, º) top

Cl1—C4	1.742 (3)	C15—H15	0.9500
Cl2—C14	1.746 (3)	C16—C17	1.476 (3)
Cl3—C24	1.744 (3)	C17—C18	1.502 (4)
O1—C1	1.321 (3)	C18—H18A	0.9800
O1—H1O	0.846 (10)	C18—H18B	0.9800
O2—C11	1.343 (3)	C18—H18C	0.9800
O2—H2O	0.846 (10)	C19—C20	1.504 (4)
O3—C21	1.318 (3)	C19—H19A	0.9900
N1—C7	1.296 (3)	C19—H19B	0.9900
N1—C9	1.459 (3)	C20—H20A	0.9900
N2—C17	1.289 (3)	C20—H20B	0.9900
N2—C19	1.465 (3)	C21—C22	1.401 (4)
N3—C27	1.293 (3)	C21—C26	1.431 (4)
N3—C29	1.457 (3)	C22—C23	1.374 (4)
N3—H3N	0.892 (10)	C22—H22	0.9500
N4—C10	1.459 (3)	C23—C24	1.393 (4)
N4—C30	1.465 (3)	C23—H23	0.9500
N4—C20	1.468 (3)	C24—C25	1.367 (4)
C1—C2	1.411 (4)	C25—C26	1.409 (3)
C1—C6	1.426 (3)	C25—H25	0.9500
C2—C3	1.371 (4)	C26—C27	1.463 (4)
C2—H2	0.9500	C27—C28	1.505 (4)
C3—C4	1.395 (4)	C28—H28A	0.9800
C3—H3	0.9500	C28—H28B	0.9800
C4—C5	1.375 (3)	C28—H28C	0.9800
C5—C6	1.405 (3)	C29—C30	1.517 (4)
C5—H5	0.9500	C29—H29A	0.9900
C6—C7	1.472 (3)	C29—H29B	0.9900
C7—C8	1.499 (3)	C30—H30A	0.9900
C8—H8A	0.9800	C30—H30B	0.9900
C8—H8B	0.9800	C31—C32	1.3900
C8—H8C	0.9800	C31—C36	1.3900
C9—C10	1.516 (3)	C31—C37	1.503 (6)
C9—H9A	0.9900	C32—C33	1.3900
C9—H9B	0.9900	C32—H32	0.9500
C10—H10A	0.9900	C33—C34	1.3900
C10—H10B	0.9900	C33—H33	0.9500
C11—C12	1.397 (4)	C34—C35	1.3900
C11—C16	1.414 (4)	C34—H34	0.9500
C12—C13	1.380 (4)	C35—C36	1.3900
C12—H12	0.9500	C35—H35	0.9500
C13—C14	1.384 (4)	C36—H36	0.9500
C13—H13	0.9500	C37—H37A	0.9800
C14—C15	1.375 (4)	C37—H37B	0.9800
C15—C16	1.402 (3)	C37—H37C	0.9800

C1—O1—H1O	105 (3)	C17—C18—H18C	109.5
C11—O2—H2O	101 (3)	H18A—C18—H18C	109.5
C7—N1—C9	122.8 (2)	H18B—C18—H18C	109.5
C17—N2—C19	120.7 (2)	N2—C19—C20	109.7 (2)
C27—N3—C29	127.2 (2)	N2—C19—H19A	109.7
C27—N3—H3N	108 (3)	C20—C19—H19A	109.7
C29—N3—H3N	124 (3)	N2—C19—H19B	109.7
C10—N4—C30	114.31 (19)	C20—C19—H19B	109.7
C10—N4—C20	114.1 (2)	H19A—C19—H19B	108.2
C30—N4—C20	114.0 (2)	N4—C20—C19	110.9 (2)
O1—C1—C2	119.6 (2)	N4—C20—H20A	109.4
O1—C1—C6	121.8 (2)	C19—C20—H20A	109.4
C2—C1—C6	118.6 (2)	N4—C20—H20B	109.4
C3—C2—C1	121.7 (2)	C19—C20—H20B	109.4
C3—C2—H2	119.2	H20A—C20—H20B	108.0
C1—C2—H2	119.2	O3—C21—C22	119.7 (2)
C2—C3—C4	119.1 (2)	O3—C21—C26	121.8 (2)
C2—C3—H3	120.4	C22—C21—C26	118.5 (2)
C4—C3—H3	120.4	C23—C22—C21	121.6 (2)
C5—C4—C3	121.1 (2)	C23—C22—H22	119.2
C5—C4—Cl1	119.0 (2)	C21—C22—H22	119.2
C3—C4—Cl1	119.8 (2)	C22—C23—C24	119.3 (3)
C4—C5—C6	120.8 (2)	C22—C23—H23	120.4
C4—C5—H5	119.6	C24—C23—H23	120.4
C6—C5—H5	119.6	C25—C24—C23	121.3 (2)
C5—C6—C1	118.5 (2)	C25—C24—Cl3	120.1 (2)
C5—C6—C7	121.4 (2)	C23—C24—Cl3	118.6 (2)
C1—C6—C7	120.1 (2)	C24—C25—C26	120.5 (2)
N1—C7—C6	116.9 (2)	C24—C25—H25	119.7
N1—C7—C8	121.8 (2)	C26—C25—H25	119.7
C6—C7—C8	121.3 (2)	C25—C26—C21	118.7 (2)
C7—C8—H8A	109.5	C25—C26—C27	121.0 (2)
C7—C8—H8B	109.5	C21—C26—C27	120.3 (2)
H8A—C8—H8B	109.5	N3—C27—C26	116.1 (2)
C7—C8—H8C	109.5	N3—C27—C28	123.3 (2)
H8A—C8—H8C	109.5	C26—C27—C28	120.6 (2)
H8B—C8—H8C	109.5	C27—C28—H28A	109.5
N1—C9—C10	110.2 (2)	C27—C28—H28B	109.5
N1—C9—H9A	109.6	H28A—C28—H28B	109.5
C10—C9—H9A	109.6	C27—C28—H28C	109.5
N1—C9—H9B	109.6	H28A—C28—H28C	109.5
C10—C9—H9B	109.6	H28B—C28—H28C	109.5
H9A—C9—H9B	108.1	N3—C29—C30	109.8 (2)
N4—C10—C9	113.3 (2)	N3—C29—H29A	109.7
N4—C10—H10A	108.9	C30—C29—H29A	109.7
C9—C10—H10A	108.9	N3—C29—H29B	109.7
N4—C10—H10B	108.9	C30—C29—H29B	109.7
C9—C10—H10B	108.9	H29A—C29—H29B	108.2
H10A—C10—H10B	107.7	N4—C30—C29	113.8 (2)
O2—C11—C12	118.0 (2)	N4—C30—H30A	108.8
O2—C11—C16	122.3 (2)	C29—C30—H30A	108.8
C12—C11—C16	119.7 (2)	N4—C30—H30B	108.8
C13—C12—C11	121.1 (3)	C29—C30—H30B	108.8
C13—C12—H12	119.4	H30A—C30—H30B	107.7
C11—C12—H12	119.4	C32—C31—C36	120.0
C12—C13—C14	118.9 (2)	C32—C31—C37	122.2 (5)
C12—C13—H13	120.6	C36—C31—C37	117.8 (5)
C14—C13—H13	120.6	C33—C32—C31	120.0
C15—C14—C13	121.5 (2)	C33—C32—H32	120.0
C15—C14—Cl2	118.5 (2)	C31—C32—H32	120.0
C13—C14—Cl2	119.9 (2)	C32—C33—C34	120.0
C14—C15—C16	120.6 (2)	C32—C33—H33	120.0
C14—C15—H15	119.7	C34—C33—H33	120.0
C16—C15—H15	119.7	C33—C34—C35	120.0
C15—C16—C11	118.2 (2)	C33—C34—H34	120.0
C15—C16—C17	121.0 (2)	C35—C34—H34	120.0
C11—C16—C17	120.7 (2)	C36—C35—C34	120.0
N2—C17—C16	116.6 (2)	C36—C35—H35	120.0
N2—C17—C18	122.5 (2)	C34—C35—H35	120.0
C16—C17—C18	120.8 (2)	C35—C36—C31	120.0
C17—C18—H18A	109.5	C35—C36—H36	120.0
C17—C18—H18B	109.5	C31—C36—H36	120.0
H18A—C18—H18B	109.5

O1—C1—C2—C3	−178.0 (2)	C11—C16—C17—N2	−2.1 (3)
C6—C1—C2—C3	1.6 (4)	C15—C16—C17—C18	−0.9 (3)
C1—C2—C3—C4	1.0 (4)	C11—C16—C17—C18	177.1 (2)
C2—C3—C4—C5	−3.0 (4)	C17—N2—C19—C20	−176.4 (2)
C2—C3—C4—Cl1	176.2 (2)	C10—N4—C20—C19	−121.4 (2)
C3—C4—C5—C6	2.3 (4)	C30—N4—C20—C19	104.7 (2)
Cl1—C4—C5—C6	−176.95 (19)	N2—C19—C20—N4	170.4 (2)
C4—C5—C6—C1	0.4 (4)	O3—C21—C22—C23	175.9 (2)
C4—C5—C6—C7	−179.5 (2)	C26—C21—C22—C23	−3.4 (4)
O1—C1—C6—C5	177.3 (2)	C21—C22—C23—C24	0.8 (4)
C2—C1—C6—C5	−2.2 (3)	C22—C23—C24—C25	2.4 (4)
O1—C1—C6—C7	−2.8 (4)	C22—C23—C24—Cl3	−177.2 (2)
C2—C1—C6—C7	177.7 (2)	C23—C24—C25—C26	−2.8 (4)
C9—N1—C7—C6	179.1 (2)	Cl3—C24—C25—C26	176.78 (19)
C9—N1—C7—C8	−0.5 (3)	C24—C25—C26—C21	0.0 (4)
C5—C6—C7—N1	−177.2 (2)	C24—C25—C26—C27	−178.9 (2)
C1—C6—C7—N1	2.9 (3)	O3—C21—C26—C25	−176.3 (2)
C5—C6—C7—C8	2.5 (3)	C22—C21—C26—C25	3.0 (3)
C1—C6—C7—C8	−177.4 (2)	O3—C21—C26—C27	2.6 (3)
C7—N1—C9—C10	−168.1 (2)	C22—C21—C26—C27	−178.1 (2)
C30—N4—C10—C9	−82.6 (2)	C29—N3—C27—C26	−175.5 (2)
C20—N4—C10—C9	143.6 (2)	C29—N3—C27—C28	4.6 (4)
N1—C9—C10—N4	−65.6 (3)	C25—C26—C27—N3	176.8 (2)
O2—C11—C12—C13	−179.5 (2)	C21—C26—C27—N3	−2.2 (3)
C16—C11—C12—C13	0.2 (4)	C25—C26—C27—C28	−3.3 (3)
C11—C12—C13—C14	0.0 (4)	C21—C26—C27—C28	177.8 (2)
C12—C13—C14—C15	−0.1 (4)	C27—N3—C29—C30	109.5 (3)
C12—C13—C14—Cl2	177.42 (19)	C10—N4—C30—C29	125.5 (2)
C13—C14—C15—C16	0.0 (4)	C20—N4—C30—C29	−100.7 (2)
Cl2—C14—C15—C16	−177.57 (18)	N3—C29—C30—N4	−72.8 (3)
C14—C15—C16—C11	0.2 (3)	C36—C31—C32—C33	0.0
C14—C15—C16—C17	178.3 (2)	C37—C31—C32—C33	−177.9 (9)
O2—C11—C16—C15	179.4 (2)	C31—C32—C33—C34	0.0
C12—C11—C16—C15	−0.4 (3)	C32—C33—C34—C35	0.0
O2—C11—C16—C17	1.4 (4)	C33—C34—C35—C36	0.0
C12—C11—C16—C17	−178.4 (2)	C34—C35—C36—C31	0.0
C19—N2—C17—C16	175.8 (2)	C32—C31—C36—C35	0.0
C19—N2—C17—C18	−3.4 (4)	C37—C31—C36—C35	177.9 (8)
C15—C16—C17—N2	179.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (1)	1.69 (2)	2.486 (3)	155 (5)
O2—H2o···N2	0.85 (1)	1.70 (2)	2.507 (3)	158 (4)
N3—H3n···O3	0.89 (1)	1.62 (2)	2.474 (3)	158 (5)

Experimental details

Crystal data
Chemical formula	C₃₀H₃₃Cl₃N₄O₃·0.5C₇H₈
M_r	650.02
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3651 (2), 11.1839 (2), 20.1594 (5)
α, β, γ (°)	100.618 (2), 97.765 (2), 98.560 (2)
V (Å³)	1591.20 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.22 × 0.18 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.931, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	14959, 7269, 4901
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.150, 1.04
No. of reflections	7269
No. of parameters	410
No. of restraints	30
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.80

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (1)	1.69 (2)	2.486 (3)	155 (5)
O2—H2o···N2	0.85 (1)	1.70 (2)	2.507 (3)	158 (4)
N3—H3n···O3	0.89 (1)	1.62 (2)	2.474 (3)	158 (5)

Acknowledgements

The authors thank the University of Malaya (grant Nos. FS339/2008 A, PS072/2007 C) 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
Kanesato, M., Ngassapa, F. N. & Yokoyama, T. (2000). Anal. Sci. 16, 781–782. Web of Science CSD CrossRef CAS 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-(Bis{2-[1-(5-chloro-2-hy­droxy­phen­yl)ethyl­­idene­amino]eth­yl}amino)­ethyl­iminio]eth­yl}-4-chloro­phenolate toluene hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{1-[2-(Bis{2-[1-(5-chloro-2-hydroxyphenyl)ethylideneamino]ethyl}amino)ethyliminio]ethyl}-4-chlorophenolate toluene hemisolvate