Acta Crystallogr Sect E Struct Rep OnlineActa Cryst. EActa Crystallographica Section E: Structure Reports Online1600-5368International Union of Crystallography215820012968323bt285510.1107/S1600536809002906ACSEBHS1600536809002906Organic Papers2-{1-[2-(Bis{2-[1-(5-chloro-2-hydroxy­phen­yl)ethyl­ideneamino]eth­yl}amino)­ethyl­iminio]eth­yl}-4-chloro­phenolate toluene hemisolvateC30H33Cl3N4O3·0.5C7H8LeeSee MunaAliHapipah Mohd.aLoKong MunaNgSeik Wenga*Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaCorrespondence e-mail: seikweng@um.edu.my01220092812009281200965Pt 2e090200o409o40920120092312009© Lee et al. 20092009This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.A full version of this article is available from Crystallography Journals Online.

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<sec id="sec2.1.1"><title>Crystal data

C30H33Cl3N4O3·0.5C7H8

M r = 650.02

Triclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 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

<p>Data collection: <italic>APEX2</italic> (Bruker, 2007<xref ref-type="bibr" rid="bb2"> ▶</xref>); cell refinement: <italic>APEX2</italic>; data reduction: <italic>SAINT</italic> (Bruker, 2007<xref ref-type="bibr" rid="bb2"> ▶</xref>); program(s) used to solve structure: <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb5"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb5"> ▶</xref>); molecular graphics: <italic>X-SEED</italic> (Barbour, 2001<xref ref-type="bibr" rid="bb1"> ▶</xref>); software used to prepare material for publication: <italic>publCIF</italic> (Westrip, 2009<xref ref-type="bibr" rid="bb6"> ▶</xref>).</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2855).

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

supplementary crystallographic information Experimental

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

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.

Figures

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

Crystal data
C30H33Cl3N4O3·0.5C7H8Z = 2
Mr = 650.02F(000) = 682
Triclinic, P1Dx = 1.357 Mg m−3
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 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
Bruker SMART APEX diffractometer7269 independent reflections
Radiation source: fine-focus sealed tube4901 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.931, Tmax = 0.993k = −14→14
14959 measured reflectionsl = −26→25
Refinement
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 = 1.04w = 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 Å−3
30 restraintsΔρmin = −0.80 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)
xyzUiso*/UeqOcc. (<1)
Cl1−0.23379 (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)
C2−0.0030 (4)0.4161 (3)0.30111 (13)0.0263 (6)
H20.04000.41740.34790.032*
C3−0.0698 (4)0.5162 (2)0.28386 (14)0.0267 (6)
H3−0.07130.58670.31820.032*
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)
H5−0.16840.41600.11820.024*
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)
H8A0.00640.19640.02950.030*
H8B−0.14100.28340.04830.030*
H8C−0.20280.13630.03250.030*
C90.0297 (3)0.0003 (2)0.09993 (13)0.0185 (5)
H9A0.13450.01840.07520.022*
H9B−0.0860−0.02780.06580.022*
C100.0625 (3)−0.1009 (2)0.13845 (13)0.0190 (5)
H10A−0.0391−0.11450.16520.023*
H10B0.0573−0.17870.10500.023*
C110.1462 (3)−0.1520 (2)0.47997 (13)0.0210 (5)
C120.0918 (4)−0.1964 (3)0.53595 (13)0.0247 (6)
H120.0335−0.28030.52980.030*
C130.1212 (4)−0.1205 (3)0.60011 (13)0.0260 (6)
H130.0837−0.15160.63790.031*
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)
H20A0.3182−0.17780.25150.031*
H20B0.1065−0.15810.24910.031*
C210.3929 (3)0.2251 (2)0.02511 (13)0.0191 (5)
C220.3371 (3)0.2955 (2)−0.02214 (14)0.0221 (5)
H220.33450.2646−0.06950.027*
C230.2860 (4)0.4080 (2)−0.00169 (15)0.0258 (6)
H230.24710.4539−0.03460.031*
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*
H29B0.6703−0.01970.14980.030*
C300.3992 (3)−0.1001 (2)0.15147 (13)0.0197 (5)
H30A0.3555−0.12820.10160.024*
H30B0.4468−0.16890.16850.024*
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 (Å<sup>2</sup>)
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, °)
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—C3−178.0 (2)C11—C16—C17—N2−2.1 (3)
C6—C1—C2—C31.6 (4)C15—C16—C17—C18−0.9 (3)
C1—C2—C3—C41.0 (4)C11—C16—C17—C18177.1 (2)
C2—C3—C4—C5−3.0 (4)C17—N2—C19—C20−176.4 (2)
C2—C3—C4—Cl1176.2 (2)C10—N4—C20—C19−121.4 (2)
C3—C4—C5—C62.3 (4)C30—N4—C20—C19104.7 (2)
Cl1—C4—C5—C6−176.95 (19)N2—C19—C20—N4170.4 (2)
C4—C5—C6—C10.4 (4)O3—C21—C22—C23175.9 (2)
C4—C5—C6—C7−179.5 (2)C26—C21—C22—C23−3.4 (4)
O1—C1—C6—C5177.3 (2)C21—C22—C23—C240.8 (4)
C2—C1—C6—C5−2.2 (3)C22—C23—C24—C252.4 (4)
O1—C1—C6—C7−2.8 (4)C22—C23—C24—Cl3−177.2 (2)
C2—C1—C6—C7177.7 (2)C23—C24—C25—C26−2.8 (4)
C9—N1—C7—C6179.1 (2)Cl3—C24—C25—C26176.78 (19)
C9—N1—C7—C8−0.5 (3)C24—C25—C26—C210.0 (4)
C5—C6—C7—N1−177.2 (2)C24—C25—C26—C27−178.9 (2)
C1—C6—C7—N12.9 (3)O3—C21—C26—C25−176.3 (2)
C5—C6—C7—C82.5 (3)C22—C21—C26—C253.0 (3)
C1—C6—C7—C8−177.4 (2)O3—C21—C26—C272.6 (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—C9143.6 (2)C29—N3—C27—C284.6 (4)
N1—C9—C10—N4−65.6 (3)C25—C26—C27—N3176.8 (2)
O2—C11—C12—C13−179.5 (2)C21—C26—C27—N3−2.2 (3)
C16—C11—C12—C130.2 (4)C25—C26—C27—C28−3.3 (3)
C11—C12—C13—C140.0 (4)C21—C26—C27—C28177.8 (2)
C12—C13—C14—C15−0.1 (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—C29−100.7 (2)
Cl2—C14—C15—C16−177.57 (18)N3—C29—C30—N4−72.8 (3)
C14—C15—C16—C110.2 (3)C36—C31—C32—C330.0
C14—C15—C16—C17178.3 (2)C37—C31—C32—C33−177.9 (9)
O2—C11—C16—C15179.4 (2)C31—C32—C33—C340.0
C12—C11—C16—C15−0.4 (3)C32—C33—C34—C350.0
O2—C11—C16—C171.4 (4)C33—C34—C35—C360.0
C12—C11—C16—C17−178.4 (2)C34—C35—C36—C310.0
C19—N2—C17—C16175.8 (2)C32—C31—C36—C350.0
C19—N2—C17—C18−3.4 (4)C37—C31—C36—C35177.9 (8)
C15—C16—C17—N2179.9 (2)
Hydrogen-bond geometry (Å, °)
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)
ReferencesBarbour, L. J. (2001). J. Supramol. Chem.1, 189–191.Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.Kanesato, M., Ngassapa, F. N. & Yokoyama, T. (2000). Anal. Sci.16, 781–782.Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Westrip, S. P. (2009). publCIF In preparation.Hydrogen-bond geometry (Å, °)
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)