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

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ISSN: 2056-9890

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

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[Kanesato, M., Ngassapa, F. N. & Yokoyama, T. (2000). Anal. Sci. 16, 781-782.]).

[Scheme 1]

Experimental

Crystal data
  • C30H33Cl3N4O3·0.5C7H8

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.931, Tmax = 0.993

  • 14959 measured reflections

  • 7269 independent reflections

  • 4901 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.79 e Å−3

  • Δρmin = −0.80 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The methyl H-atoms were rotated to fit the electron density.

The toluene molecule is disordered about a center-of-inversion; the aromatic ring was refined as a rigid hexagon of 0.5 site occupancy. The 1,2-related distance involving the methyl carbon was restrained to 1.50±0.01 Å and the 1,3-related ones to 2.50±0.01 Å. The anisotropic displacement parameters of the seven carbon atoms were restrained to be nearly isotropic.

The iminium and hydroxy H-atoms were located in a difference Fourier map and they were freely refined.

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
[Figure 1] 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
C30H33Cl3N4O3·0.5C7H8Z = 2
Mr = 650.02F(000) = 682
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3651 (2) ÅCell parameters from 3243 reflections
b = 11.1839 (2) Åθ = 2.3–29.3°
c = 20.1594 (5) ŵ = 0.33 mm1
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 tube4901 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.931, Tmax = 0.993k = 1414
14959 measured reflectionsl = 2625
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0807P)2 + 0.0533P]
where P = (Fo2 + 2Fc2)/3
7269 reflections(Δ/σ)max = 0.001
410 parametersΔρmax = 0.79 e Å3
30 restraintsΔρmin = 0.80 e Å3
Crystal data top
C30H33Cl3N4O3·0.5C7H8γ = 98.560 (2)°
Mr = 650.02V = 1591.20 (7) Å3
Triclinic, P1Z = 2
a = 7.3651 (2) ÅMo Kα radiation
b = 11.1839 (2) ŵ = 0.33 mm1
c = 20.1594 (5) ÅT = 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)
Tmin = 0.931, Tmax = 0.993Rint = 0.033
14959 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05030 restraints
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.79 e Å3
7269 reflectionsΔρmin = 0.80 e Å3
410 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.23379 (11)0.63575 (6)0.19284 (4)0.03291 (19)
Cl20.23675 (10)0.10135 (7)0.68824 (3)0.03301 (19)
Cl30.21656 (11)0.59383 (6)0.09250 (5)0.0398 (2)
O10.0640 (3)0.21520 (18)0.27035 (9)0.0250 (4)
O20.1122 (3)0.23059 (17)0.41888 (9)0.0268 (4)
O30.4300 (2)0.11432 (15)0.00308 (9)0.0209 (4)
N10.0135 (3)0.11221 (18)0.14742 (10)0.0173 (4)
N20.2570 (3)0.05363 (19)0.37189 (10)0.0203 (5)
N30.5052 (3)0.0992 (2)0.12427 (11)0.0194 (4)
N40.2407 (3)0.07266 (19)0.18467 (10)0.0185 (4)
C10.0036 (3)0.3111 (2)0.25116 (13)0.0202 (5)
C20.0030 (4)0.4161 (3)0.30111 (13)0.0263 (6)
H20.04000.41740.34790.032*
C30.0698 (4)0.5162 (2)0.28386 (14)0.0267 (6)
H30.07130.58670.31820.032*
C40.1358 (4)0.5134 (2)0.21528 (13)0.0229 (6)
C50.1268 (3)0.4145 (2)0.16472 (13)0.0196 (5)
H50.16840.41600.11820.024*
C60.0570 (3)0.3114 (2)0.18097 (12)0.0172 (5)
C70.0454 (3)0.2053 (2)0.12730 (12)0.0159 (5)
C80.1005 (3)0.2054 (2)0.05297 (12)0.0199 (5)
H8A0.00640.19640.02950.030*
H8B0.14100.28340.04830.030*
H8C0.20280.13630.03250.030*
C90.0297 (3)0.0003 (2)0.09993 (13)0.0185 (5)
H9A0.13450.01840.07520.022*
H9B0.08600.02780.06580.022*
C100.0625 (3)0.1009 (2)0.13845 (13)0.0190 (5)
H10A0.03910.11450.16520.023*
H10B0.05730.17870.10500.023*
C110.1462 (3)0.1520 (2)0.47997 (13)0.0210 (5)
C120.0918 (4)0.1964 (3)0.53595 (13)0.0247 (6)
H120.03350.28030.52980.030*
C130.1212 (4)0.1205 (3)0.60011 (13)0.0260 (6)
H130.08370.15160.63790.031*
C140.2062 (3)0.0015 (3)0.60846 (13)0.0238 (6)
C150.2619 (3)0.0482 (2)0.55447 (13)0.0215 (5)
H150.31990.13230.56170.026*
C160.2337 (3)0.0273 (2)0.48890 (12)0.0188 (5)
C170.2881 (3)0.0227 (2)0.43020 (12)0.0193 (5)
C180.3728 (4)0.1565 (2)0.43895 (14)0.0266 (6)
H18A0.31270.19050.40200.040*
H18B0.50640.16390.43740.040*
H18C0.35460.20250.48320.040*
C190.2943 (4)0.0111 (2)0.30971 (12)0.0241 (6)
H19A0.42890.02140.31410.029*
H19B0.22530.05660.30340.029*
C200.2347 (4)0.1166 (3)0.24873 (13)0.0256 (6)
H20A0.31820.17780.25150.031*
H20B0.10650.15810.24910.031*
C210.3929 (3)0.2251 (2)0.02511 (13)0.0191 (5)
C220.3371 (3)0.2955 (2)0.02214 (14)0.0221 (5)
H220.33450.26460.06950.027*
C230.2860 (4)0.4080 (2)0.00169 (15)0.0258 (6)
H230.24710.45390.03460.031*
C240.2918 (4)0.4542 (2)0.06778 (15)0.0251 (6)
C250.3537 (3)0.3918 (2)0.11611 (14)0.0238 (6)
H250.36160.42690.16330.029*
C260.4060 (3)0.2759 (2)0.09650 (13)0.0190 (5)
C270.4692 (3)0.2072 (2)0.14771 (13)0.0203 (5)
C280.4898 (4)0.2621 (3)0.22289 (13)0.0263 (6)
H28A0.55940.21330.24930.040*
H28B0.36620.26120.23590.040*
H28C0.55720.34740.23240.040*
C290.5577 (3)0.0091 (2)0.16366 (14)0.0249 (6)
H29A0.58690.04810.21300.030*
H29B0.67030.01970.14980.030*
C300.3992 (3)0.1001 (2)0.15147 (13)0.0197 (5)
H30A0.35550.12820.10160.024*
H30B0.44680.16890.16850.024*
C310.4925 (19)0.5285 (12)0.4490 (5)0.083 (3)0.50
C320.3426 (19)0.5415 (12)0.4832 (5)0.059 (3)0.50
H320.24190.57540.46410.071*0.50
C330.340 (2)0.5050 (13)0.5454 (5)0.089 (3)0.50
H330.23760.51390.56880.107*0.50
C340.487 (2)0.4554 (12)0.5734 (5)0.083 (3)0.50
H340.48560.43050.61590.100*0.50
C350.637 (2)0.4424 (12)0.5392 (5)0.059 (3)0.50
H350.73790.40850.55840.071*0.50
C360.6399 (19)0.4789 (12)0.4770 (5)0.089 (3)0.50
H360.74230.47000.45370.107*0.50
C370.5056 (18)0.5705 (11)0.3829 (5)0.123 (5)0.50
H37A0.42890.63420.37920.185*0.50
H37B0.46080.50000.34440.185*0.50
H37C0.63550.60460.38200.185*0.50
H1O0.055 (7)0.163 (4)0.2335 (15)0.109 (19)*
H2O0.150 (5)0.183 (3)0.3934 (17)0.070 (13)*
H3N0.484 (7)0.086 (5)0.0787 (6)0.106 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0467 (4)0.0175 (3)0.0363 (4)0.0104 (3)0.0104 (3)0.0038 (3)
Cl20.0319 (4)0.0504 (4)0.0164 (3)0.0158 (3)0.0031 (3)0.0000 (3)
Cl30.0402 (4)0.0188 (3)0.0650 (5)0.0116 (3)0.0178 (4)0.0090 (3)
O10.0271 (10)0.0307 (10)0.0202 (10)0.0102 (8)0.0048 (8)0.0083 (8)
O20.0335 (11)0.0250 (10)0.0218 (10)0.0038 (9)0.0068 (8)0.0040 (8)
O30.0219 (9)0.0183 (8)0.0240 (9)0.0072 (7)0.0046 (7)0.0047 (7)
N10.0129 (10)0.0182 (10)0.0211 (11)0.0020 (8)0.0049 (8)0.0042 (8)
N20.0199 (11)0.0250 (11)0.0180 (11)0.0057 (9)0.0054 (8)0.0066 (9)
N30.0152 (10)0.0222 (11)0.0229 (12)0.0020 (8)0.0034 (9)0.0106 (9)
N40.0176 (10)0.0238 (11)0.0159 (10)0.0042 (9)0.0049 (8)0.0073 (8)
C10.0168 (12)0.0246 (13)0.0192 (12)0.0012 (10)0.0055 (10)0.0044 (10)
C20.0269 (14)0.0314 (14)0.0178 (13)0.0006 (12)0.0041 (11)0.0010 (11)
C30.0286 (14)0.0230 (13)0.0242 (14)0.0005 (11)0.0067 (11)0.0043 (11)
C40.0230 (13)0.0178 (12)0.0278 (14)0.0010 (10)0.0072 (11)0.0040 (11)
C50.0197 (12)0.0185 (12)0.0202 (13)0.0009 (10)0.0037 (10)0.0050 (10)
C60.0143 (11)0.0195 (12)0.0181 (12)0.0005 (10)0.0043 (9)0.0051 (10)
C70.0112 (11)0.0184 (12)0.0185 (12)0.0013 (9)0.0045 (9)0.0045 (10)
C80.0213 (13)0.0206 (12)0.0194 (12)0.0061 (10)0.0051 (10)0.0053 (10)
C90.0155 (12)0.0184 (12)0.0217 (13)0.0042 (10)0.0030 (10)0.0037 (10)
C100.0134 (11)0.0209 (12)0.0233 (13)0.0023 (10)0.0043 (10)0.0060 (10)
C110.0191 (12)0.0276 (13)0.0184 (13)0.0084 (11)0.0043 (10)0.0058 (10)
C120.0204 (13)0.0308 (14)0.0264 (14)0.0083 (11)0.0045 (11)0.0115 (12)
C130.0217 (13)0.0415 (16)0.0207 (13)0.0128 (12)0.0078 (11)0.0126 (12)
C140.0189 (13)0.0384 (15)0.0149 (12)0.0127 (12)0.0015 (10)0.0020 (11)
C150.0177 (12)0.0250 (13)0.0223 (13)0.0089 (11)0.0006 (10)0.0042 (11)
C160.0132 (12)0.0255 (13)0.0190 (12)0.0074 (10)0.0023 (9)0.0051 (10)
C170.0135 (11)0.0257 (13)0.0200 (13)0.0071 (10)0.0024 (10)0.0055 (10)
C180.0282 (14)0.0257 (14)0.0253 (14)0.0020 (12)0.0060 (11)0.0048 (11)
C190.0276 (14)0.0272 (14)0.0189 (13)0.0047 (11)0.0072 (11)0.0066 (11)
C200.0301 (15)0.0285 (14)0.0197 (13)0.0024 (12)0.0073 (11)0.0091 (11)
C210.0115 (11)0.0171 (12)0.0299 (14)0.0016 (9)0.0054 (10)0.0072 (10)
C220.0179 (12)0.0243 (13)0.0259 (14)0.0033 (10)0.0057 (10)0.0082 (11)
C230.0179 (13)0.0220 (13)0.0413 (16)0.0020 (10)0.0072 (12)0.0158 (12)
C240.0203 (13)0.0141 (12)0.0424 (16)0.0022 (10)0.0106 (12)0.0062 (11)
C250.0177 (13)0.0195 (12)0.0320 (15)0.0008 (10)0.0073 (11)0.0012 (11)
C260.0134 (11)0.0192 (12)0.0240 (13)0.0009 (10)0.0043 (10)0.0053 (10)
C270.0118 (11)0.0233 (13)0.0246 (13)0.0031 (10)0.0051 (10)0.0051 (11)
C280.0243 (14)0.0301 (14)0.0234 (14)0.0007 (12)0.0069 (11)0.0050 (11)
C290.0160 (12)0.0314 (14)0.0315 (15)0.0048 (11)0.0032 (11)0.0172 (12)
C300.0166 (12)0.0226 (12)0.0241 (13)0.0080 (10)0.0057 (10)0.0102 (10)
C310.112 (5)0.036 (4)0.081 (7)0.007 (3)0.021 (5)0.009 (4)
C320.058 (3)0.036 (3)0.072 (6)0.019 (3)0.013 (4)0.008 (4)
C330.090 (4)0.050 (4)0.109 (7)0.023 (3)0.030 (5)0.009 (5)
C340.112 (5)0.036 (4)0.081 (7)0.007 (3)0.021 (5)0.009 (4)
C350.058 (3)0.036 (3)0.072 (6)0.019 (3)0.013 (4)0.008 (4)
C360.090 (4)0.050 (4)0.109 (7)0.023 (3)0.030 (5)0.009 (5)
C370.142 (8)0.097 (7)0.118 (8)0.017 (6)0.060 (7)0.009 (6)
Geometric parameters (Å, º) top
Cl1—C41.742 (3)C15—H150.9500
Cl2—C141.746 (3)C16—C171.476 (3)
Cl3—C241.744 (3)C17—C181.502 (4)
O1—C11.321 (3)C18—H18A0.9800
O1—H1O0.846 (10)C18—H18B0.9800
O2—C111.343 (3)C18—H18C0.9800
O2—H2O0.846 (10)C19—C201.504 (4)
O3—C211.318 (3)C19—H19A0.9900
N1—C71.296 (3)C19—H19B0.9900
N1—C91.459 (3)C20—H20A0.9900
N2—C171.289 (3)C20—H20B0.9900
N2—C191.465 (3)C21—C221.401 (4)
N3—C271.293 (3)C21—C261.431 (4)
N3—C291.457 (3)C22—C231.374 (4)
N3—H3N0.892 (10)C22—H220.9500
N4—C101.459 (3)C23—C241.393 (4)
N4—C301.465 (3)C23—H230.9500
N4—C201.468 (3)C24—C251.367 (4)
C1—C21.411 (4)C25—C261.409 (3)
C1—C61.426 (3)C25—H250.9500
C2—C31.371 (4)C26—C271.463 (4)
C2—H20.9500C27—C281.505 (4)
C3—C41.395 (4)C28—H28A0.9800
C3—H30.9500C28—H28B0.9800
C4—C51.375 (3)C28—H28C0.9800
C5—C61.405 (3)C29—C301.517 (4)
C5—H50.9500C29—H29A0.9900
C6—C71.472 (3)C29—H29B0.9900
C7—C81.499 (3)C30—H30A0.9900
C8—H8A0.9800C30—H30B0.9900
C8—H8B0.9800C31—C321.3900
C8—H8C0.9800C31—C361.3900
C9—C101.516 (3)C31—C371.503 (6)
C9—H9A0.9900C32—C331.3900
C9—H9B0.9900C32—H320.9500
C10—H10A0.9900C33—C341.3900
C10—H10B0.9900C33—H330.9500
C11—C121.397 (4)C34—C351.3900
C11—C161.414 (4)C34—H340.9500
C12—C131.380 (4)C35—C361.3900
C12—H120.9500C35—H350.9500
C13—C141.384 (4)C36—H360.9500
C13—H130.9500C37—H37A0.9800
C14—C151.375 (4)C37—H37B0.9800
C15—C161.402 (3)C37—H37C0.9800
C1—O1—H1O105 (3)C17—C18—H18C109.5
C11—O2—H2O101 (3)H18A—C18—H18C109.5
C7—N1—C9122.8 (2)H18B—C18—H18C109.5
C17—N2—C19120.7 (2)N2—C19—C20109.7 (2)
C27—N3—C29127.2 (2)N2—C19—H19A109.7
C27—N3—H3N108 (3)C20—C19—H19A109.7
C29—N3—H3N124 (3)N2—C19—H19B109.7
C10—N4—C30114.31 (19)C20—C19—H19B109.7
C10—N4—C20114.1 (2)H19A—C19—H19B108.2
C30—N4—C20114.0 (2)N4—C20—C19110.9 (2)
O1—C1—C2119.6 (2)N4—C20—H20A109.4
O1—C1—C6121.8 (2)C19—C20—H20A109.4
C2—C1—C6118.6 (2)N4—C20—H20B109.4
C3—C2—C1121.7 (2)C19—C20—H20B109.4
C3—C2—H2119.2H20A—C20—H20B108.0
C1—C2—H2119.2O3—C21—C22119.7 (2)
C2—C3—C4119.1 (2)O3—C21—C26121.8 (2)
C2—C3—H3120.4C22—C21—C26118.5 (2)
C4—C3—H3120.4C23—C22—C21121.6 (2)
C5—C4—C3121.1 (2)C23—C22—H22119.2
C5—C4—Cl1119.0 (2)C21—C22—H22119.2
C3—C4—Cl1119.8 (2)C22—C23—C24119.3 (3)
C4—C5—C6120.8 (2)C22—C23—H23120.4
C4—C5—H5119.6C24—C23—H23120.4
C6—C5—H5119.6C25—C24—C23121.3 (2)
C5—C6—C1118.5 (2)C25—C24—Cl3120.1 (2)
C5—C6—C7121.4 (2)C23—C24—Cl3118.6 (2)
C1—C6—C7120.1 (2)C24—C25—C26120.5 (2)
N1—C7—C6116.9 (2)C24—C25—H25119.7
N1—C7—C8121.8 (2)C26—C25—H25119.7
C6—C7—C8121.3 (2)C25—C26—C21118.7 (2)
C7—C8—H8A109.5C25—C26—C27121.0 (2)
C7—C8—H8B109.5C21—C26—C27120.3 (2)
H8A—C8—H8B109.5N3—C27—C26116.1 (2)
C7—C8—H8C109.5N3—C27—C28123.3 (2)
H8A—C8—H8C109.5C26—C27—C28120.6 (2)
H8B—C8—H8C109.5C27—C28—H28A109.5
N1—C9—C10110.2 (2)C27—C28—H28B109.5
N1—C9—H9A109.6H28A—C28—H28B109.5
C10—C9—H9A109.6C27—C28—H28C109.5
N1—C9—H9B109.6H28A—C28—H28C109.5
C10—C9—H9B109.6H28B—C28—H28C109.5
H9A—C9—H9B108.1N3—C29—C30109.8 (2)
N4—C10—C9113.3 (2)N3—C29—H29A109.7
N4—C10—H10A108.9C30—C29—H29A109.7
C9—C10—H10A108.9N3—C29—H29B109.7
N4—C10—H10B108.9C30—C29—H29B109.7
C9—C10—H10B108.9H29A—C29—H29B108.2
H10A—C10—H10B107.7N4—C30—C29113.8 (2)
O2—C11—C12118.0 (2)N4—C30—H30A108.8
O2—C11—C16122.3 (2)C29—C30—H30A108.8
C12—C11—C16119.7 (2)N4—C30—H30B108.8
C13—C12—C11121.1 (3)C29—C30—H30B108.8
C13—C12—H12119.4H30A—C30—H30B107.7
C11—C12—H12119.4C32—C31—C36120.0
C12—C13—C14118.9 (2)C32—C31—C37122.2 (5)
C12—C13—H13120.6C36—C31—C37117.8 (5)
C14—C13—H13120.6C33—C32—C31120.0
C15—C14—C13121.5 (2)C33—C32—H32120.0
C15—C14—Cl2118.5 (2)C31—C32—H32120.0
C13—C14—Cl2119.9 (2)C32—C33—C34120.0
C14—C15—C16120.6 (2)C32—C33—H33120.0
C14—C15—H15119.7C34—C33—H33120.0
C16—C15—H15119.7C33—C34—C35120.0
C15—C16—C11118.2 (2)C33—C34—H34120.0
C15—C16—C17121.0 (2)C35—C34—H34120.0
C11—C16—C17120.7 (2)C36—C35—C34120.0
N2—C17—C16116.6 (2)C36—C35—H35120.0
N2—C17—C18122.5 (2)C34—C35—H35120.0
C16—C17—C18120.8 (2)C35—C36—C31120.0
C17—C18—H18A109.5C35—C36—H36120.0
C17—C18—H18B109.5C31—C36—H36120.0
H18A—C18—H18B109.5
O1—C1—C2—C3178.0 (2)C11—C16—C17—N22.1 (3)
C6—C1—C2—C31.6 (4)C15—C16—C17—C180.9 (3)
C1—C2—C3—C41.0 (4)C11—C16—C17—C18177.1 (2)
C2—C3—C4—C53.0 (4)C17—N2—C19—C20176.4 (2)
C2—C3—C4—Cl1176.2 (2)C10—N4—C20—C19121.4 (2)
C3—C4—C5—C62.3 (4)C30—N4—C20—C19104.7 (2)
Cl1—C4—C5—C6176.95 (19)N2—C19—C20—N4170.4 (2)
C4—C5—C6—C10.4 (4)O3—C21—C22—C23175.9 (2)
C4—C5—C6—C7179.5 (2)C26—C21—C22—C233.4 (4)
O1—C1—C6—C5177.3 (2)C21—C22—C23—C240.8 (4)
C2—C1—C6—C52.2 (3)C22—C23—C24—C252.4 (4)
O1—C1—C6—C72.8 (4)C22—C23—C24—Cl3177.2 (2)
C2—C1—C6—C7177.7 (2)C23—C24—C25—C262.8 (4)
C9—N1—C7—C6179.1 (2)Cl3—C24—C25—C26176.78 (19)
C9—N1—C7—C80.5 (3)C24—C25—C26—C210.0 (4)
C5—C6—C7—N1177.2 (2)C24—C25—C26—C27178.9 (2)
C1—C6—C7—N12.9 (3)O3—C21—C26—C25176.3 (2)
C5—C6—C7—C82.5 (3)C22—C21—C26—C253.0 (3)
C1—C6—C7—C8177.4 (2)O3—C21—C26—C272.6 (3)
C7—N1—C9—C10168.1 (2)C22—C21—C26—C27178.1 (2)
C30—N4—C10—C982.6 (2)C29—N3—C27—C26175.5 (2)
C20—N4—C10—C9143.6 (2)C29—N3—C27—C284.6 (4)
N1—C9—C10—N465.6 (3)C25—C26—C27—N3176.8 (2)
O2—C11—C12—C13179.5 (2)C21—C26—C27—N32.2 (3)
C16—C11—C12—C130.2 (4)C25—C26—C27—C283.3 (3)
C11—C12—C13—C140.0 (4)C21—C26—C27—C28177.8 (2)
C12—C13—C14—C150.1 (4)C27—N3—C29—C30109.5 (3)
C12—C13—C14—Cl2177.42 (19)C10—N4—C30—C29125.5 (2)
C13—C14—C15—C160.0 (4)C20—N4—C30—C29100.7 (2)
Cl2—C14—C15—C16177.57 (18)N3—C29—C30—N472.8 (3)
C14—C15—C16—C110.2 (3)C36—C31—C32—C330.0
C14—C15—C16—C17178.3 (2)C37—C31—C32—C33177.9 (9)
O2—C11—C16—C15179.4 (2)C31—C32—C33—C340.0
C12—C11—C16—C150.4 (3)C32—C33—C34—C350.0
O2—C11—C16—C171.4 (4)C33—C34—C35—C360.0
C12—C11—C16—C17178.4 (2)C34—C35—C36—C310.0
C19—N2—C17—C16175.8 (2)C32—C31—C36—C350.0
C19—N2—C17—C183.4 (4)C37—C31—C36—C35177.9 (8)
C15—C16—C17—N2179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.85 (1)1.69 (2)2.486 (3)155 (5)
O2—H2o···N20.85 (1)1.70 (2)2.507 (3)158 (4)
N3—H3n···O30.89 (1)1.62 (2)2.474 (3)158 (5)

Experimental details

Crystal data
Chemical formulaC30H33Cl3N4O3·0.5C7H8
Mr650.02
Crystal system, space groupTriclinic, 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)
V3)1591.20 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.22 × 0.18 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.931, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
14959, 7269, 4901
Rint0.033
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.150, 1.04
No. of reflections7269
No. of parameters410
No. of restraints30
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1o···N10.85 (1)1.69 (2)2.486 (3)155 (5)
O2—H2o···N20.85 (1)1.70 (2)2.507 (3)158 (4)
N3—H3n···O30.89 (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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKanesato, M., Ngassapa, F. N. & Yokoyama, T. (2000). Anal. Sci. 16, 781–782.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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