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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o409.
Published online 2009 January 28. doi:  10.1107/S1600536809002906
PMCID: PMC2968323

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

Abstract

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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o409-scheme1.jpg

Experimental

Crystal data

  • C30H33Cl3N4O3·0.5C7H8
  • M r = 650.02
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o409-efi1.jpg
  • 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 [triangle]) 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

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

Table 1
Hydrogen-bond geometry (Å, °)

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

Acknowledgments

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

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.

Crystal data

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

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 Å3
30 restraintsΔρmin = −0.80 e Å3

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

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 (Å2)

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)

Footnotes

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

References

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  • 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. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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