supplementary materials


nc2304 scheme

Acta Cryst. (2013). E69, o365-o366    [ doi:10.1107/S1600536813003498 ]

3,7,11-Tris{4-[(1R,3S,4S)-neomenthyloxy]phenyl}tri[1,2,4]triazolo[4,3-a:4',3'-c:4'',3''-e][1,3,5]triazine-chloroform-ethanol (1/1/1)

K. Herget, D. Schollmeyer and H. Detert

Abstract top

The title compound, C54H69N9O3·CHCl3·C2H5OH, was prepared by a threefold nucleophilic substitution of p-neomenthyloxyphenyltetrazole on cyanuric chloride followed by threefold cycloelimination of nitrogen and ring closure. The central tristriazolotriazine is roughly planar with a maximum deviation of 0.089 (7) Å but the adjacent benzene rings are twisted out of this plane. N-C-C-C torsion angles of -80.2 (9), 159.3 (7) and 50.6 (10)° destroy the formal C3 symmetry. Cavities are found between the phenoxy residues: one is occupied by a chloroform molecule, another by ethanol forming a hydrogen bond to a triazole ring while two isopropyl groups point into the third void. One methyl group and the chlorofrm molecule are disorderd and were refined using a split model.

Comment top

As part of a larger project on discotic molecules for optical and LC applications (Schmitt et al. 2011; Borchmann et al. 2010) we prepared the title compound as a chiral dopant for columnar LC phases of tristriazolotriazines (Christiano et al. 2008, Glang et al. 2013). The central tristriazolotriazine system is essentially planar with a maximal deviation of 0.089 (7) Å at C1 from the mean plane. The three benzene ring are twisted out of this plane, the torsion angles are -80.2 (9)° (N2—C1—C16—C17), 159.3 (7)° (N7—C6—C33—C34), and 50.6 (10)° (N12—C11—C50—C55).

The voluminous neomethyl residues inhibit a close packing of the tristriazolotriazines, the empty space is filled in part with solvent molecules. A disordered chloroform molecule and an ethanol molecule flank the orthogonal benzene ring, the alcohol forms a hydrogen bridge (O2l—H2l···N12) to N12 of the triazole.

All neomethyl units adopt conformations with equatorial methyl and isopropyl groups. Like the torsion of the benzene rings, the orientation of the neomenthyl goups break the possible C3 symmetry: Two isopropyl groups point into the empty space, the third one is oriented to the space occupied with the smaller solvent molecule.

Related literature top

For the synthesis of related tristriazolotriazines, see: Hofmann & Erhardt (1912); Huisgen et al. (1961); Glang et al. (2008). For structures of tetrazoles, see: Rieth et al. (2011). For structures of related tristriazolotriazines, see: Christiano et al. (2008). For liquid-crystalline tristriazolotriazines, see: Christiano et al. (2008, 2012); Glang et al. (2013). For isomeric tristriazolotriazines, see: Tartakovsky et al. (2005); Borchmann et al. (2010). For star-shaped conjugated oligomers, see: Schmitt et al. (2011); Detert et al. (2010).

Experimental top

3,7,11-Tris-(4-(1R,3S,4S)-neomenthyloxyphenyl)tris([1,2,4] triazolo)[4,3 - a:4',3'-c:4'',3''-e][1,3,5]triazine: 5-(4-Neomenthyloxyphenyl)tetrazole was prepared by a Mitsunobu-reaction of p-cyanophenol and (-)-menthol (53%) followed by an addition of hydrazoic acid (NaN3, Et3NHCl, toluene, 87%, mp: 513 K), and recrystallization from ethanol/toluene. Collidine (1 ml) was added to a stirred suspension of the tetrazole (500 mg, 1.66 mmol) and cyanuric chloride (93 mg, 0.5 mmol) in xylenes. After stirring for 16 h, the mixture was slowly heated to 343 K (4 h). Hydrochloric acid (2 N, 10 ml) was added and the organic layer diluted with ethyl acetate (100 ml). The organic solution was washed with water and brine, dried, and concentrated. Purification by column chromatography (basic aluminium oxide, toluene/ethyl acetate = 19/1 (v/v)). Yield: 213 mg (70%) of an off-white solid with m.p. = 484–485 K. Single crystals were obtained from slow crystallization from chloroform/ethanol

Refinement top

Hydrogen atoms attached to carbons and oxygen were placed at calculated positions (methyl H atoms allowed to rotate but not to tip) with C—H = 0.93 Å for aromatic, 0.97 Å for methylene, 0.96 Å for methyl H atoms and 0.84 Å for O—H distance and were refined in the riding-model approximation with a common isotropic displacement parameters for those H atoms connected to the same C atom. One methyl group (C63) and the trichloromethan molecule are disorderd. The C62–C63/C63a distances were refined assuming standard C–C distances (1.54 (2) Å). Thermal parameters for C63,C63a and the solvent CHCl3 molecule are restrained to isotropic manner. The absolute structure was determined on the basis of 4585 Friedel pairs.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2011); cell refinement: X-AREA (Stoe & Cie, 2011); data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.
3,7,11-Tris{4-[(1R,3S,4S)-neomenthyloxy]phenyl}tri[1,2,4]triazolo[4,3-a:4',3'-c:4'',3''-e][1,3,5]triazine–chloroform–ethanol (1/1/1) top
Crystal data top
C54H69N9O3·CHCl3·C2H6ODx = 1.232 Mg m3
Mr = 1057.62Melting point: 422 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8050 reflections
a = 6.6562 (5) Åθ = 2.2–25.0°
b = 14.1000 (14) ŵ = 0.21 mm1
c = 60.756 (5) ÅT = 193 K
V = 5702.1 (8) Å3Needle, colourless
Z = 40.5 × 0.06 × 0.02 mm
F(000) = 2256
Data collection top
Stoe IPDS 2T
diffractometer
2815 reflections with I > 2σ(I)
Radiation source: sealed TubeRint = 0.168
Graphite monochromatorθmax = 25.8°, θmin = 2.2°
Detector resolution: 6.67 pixels mm-1h = 78
rotation method scansk = 1717
32105 measured reflectionsl = 7474
10791 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0337P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.78(Δ/σ)max = 0.001
10791 reflectionsΔρmax = 0.31 e Å3
687 parametersΔρmin = 0.25 e Å3
26 restraintsAbsolute structure: Flack (1983), 4585 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (14)
Crystal data top
C54H69N9O3·CHCl3·C2H6OV = 5702.1 (8) Å3
Mr = 1057.62Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.6562 (5) ŵ = 0.21 mm1
b = 14.1000 (14) ÅT = 193 K
c = 60.756 (5) Å0.5 × 0.06 × 0.02 mm
Data collection top
Stoe IPDS 2T
diffractometer
2815 reflections with I > 2σ(I)
32105 measured reflectionsRint = 0.168
10791 independent reflectionsθmax = 25.8°
Refinement top
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.153Δρmax = 0.31 e Å3
S = 0.78Δρmin = 0.25 e Å3
10791 reflectionsAbsolute structure: Flack (1983), 4585 Friedel pairs
687 parametersFlack parameter: 0.03 (14)
26 restraints
Special details top

Experimental. H-NMR (300 MHz, CDCl3): 8.10 ("d", 6 H, 2-H, 6-H, phenyl), 7.07 ("d", 6 H, 3-H, 5-H, phenyl), 4.76 (bs, 3 H) 2.17 (dq, 3 H, J = 15 Hz, J = 2.3 Hz), 1.84 - 1.67 (m, 15 H), 1.18 - 0.95 (m, 9 H), 0.95 (d, J = 8.1 Hz, 9 H), 0.88 (d, 9 H), 0.86 (d, 9 H).

C-NMR (75 MHz, CDCl3): 161.4, 151.2, 140.6, 132.1, 115.4, 115.4, 73.7, 47.2, 37.7, 35.1, 29.4, 26.4, 25.0, 22.4, 21.2, 21.0.

IR (ATR): 2945, 2924, 2868, 2845, 2350, 1592, 1530, 1480, 1457, 1427, 1369, 1290, 1252, 1223, 1200, 1176, 1150, 1121, 1025, 1012, 963, 940, 910, 892, 832, 730, 708.

MS (FD): 1784 (1%) [M2]+; 892 (100%) [M]+; 755 (1%) [M - neomenthyl]

Combustion analysis: calc. for C54H69N9O3: C: 72.70%, H: 7.80%, N: 14.13%. Found: C: 72.36%, H: 7.86%, N: 14.09%.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.8472 (11)0.8349 (5)0.89333 (11)0.0467 (18)
N20.7047 (9)0.8376 (4)0.90835 (9)0.0569 (17)
N30.5733 (9)0.7602 (4)0.90507 (9)0.0561 (16)
C40.6395 (11)0.7149 (5)0.88820 (11)0.0483 (19)
N50.5718 (9)0.6368 (3)0.87701 (8)0.0432 (14)
C60.4029 (11)0.5766 (5)0.87885 (11)0.0482 (18)
N70.4046 (9)0.5156 (4)0.86296 (9)0.0510 (16)
N80.5717 (10)0.5318 (4)0.84955 (9)0.0566 (16)
C90.6616 (12)0.6032 (5)0.85831 (10)0.0472 (19)
N100.8375 (9)0.6470 (4)0.85141 (8)0.0447 (15)
N121.1267 (9)0.6842 (4)0.83695 (9)0.0566 (17)
N131.0943 (10)0.7462 (4)0.85493 (9)0.0549 (16)
C110.9779 (12)0.6261 (5)0.83499 (10)0.049 (2)
C140.9214 (12)0.7215 (5)0.86274 (11)0.0473 (19)
N150.8146 (9)0.7560 (4)0.88032 (8)0.0453 (15)
C160.9937 (12)0.9092 (5)0.88891 (11)0.051 (2)
C170.9390 (13)0.9861 (6)0.87639 (12)0.079 (2)
H170.80620.98970.87080.094*
C181.0719 (13)1.0574 (5)0.87186 (12)0.070 (2)
H181.03071.11000.86320.084*
C191.2640 (13)1.0533 (6)0.87984 (12)0.057 (2)
C201.3199 (12)0.9785 (5)0.89251 (12)0.067 (2)
H201.45250.97600.89830.080*
C211.1854 (13)0.9051 (5)0.89720 (12)0.068 (2)
H211.22620.85290.90600.081*
O221.4113 (7)1.1184 (3)0.87552 (7)0.0593 (13)
C231.3491 (12)1.2162 (5)0.87097 (12)0.059 (2)
H231.24881.21670.85870.071*
C241.2581 (11)1.2595 (5)0.89107 (13)0.068 (2)
H24A1.13831.22210.89530.082*
H24B1.21231.32450.88740.082*
C251.3987 (14)1.2647 (5)0.91061 (13)0.074 (2)
H251.43961.19890.91480.089*
C261.5830 (15)1.3194 (6)0.90378 (16)0.100 (3)
H26A1.68021.32050.91610.120*
H26B1.54491.38570.90040.120*
C271.6812 (13)1.2752 (6)0.88377 (15)0.084 (3)
H27A1.72991.21110.88770.101*
H27B1.79951.31390.87960.101*
C281.5402 (12)1.2670 (5)0.86361 (15)0.073 (2)
H281.50071.33300.85940.087*
C291.2996 (14)1.3120 (6)0.93033 (14)0.110 (3)
H29A1.25661.37610.92630.164*
H29B1.39581.31550.94250.164*
H29C1.18251.27480.93490.164*
C301.6331 (13)1.2217 (6)0.84330 (16)0.085 (3)
H301.68381.15740.84740.103*
C311.4876 (15)1.2106 (6)0.82425 (13)0.118 (4)
H31A1.45521.27320.81820.177*
H31B1.36421.18000.82950.177*
H31C1.54931.17140.81280.177*
C321.8185 (14)1.2838 (6)0.83536 (16)0.127 (4)
H32A1.92361.28270.84670.190*
H32B1.77461.34930.83290.190*
H32C1.87181.25760.82160.190*
C330.2432 (12)0.5763 (5)0.89560 (11)0.051 (2)
C340.2663 (12)0.6180 (6)0.91587 (11)0.073 (3)
H340.38880.64940.91930.088*
C350.1134 (12)0.6154 (6)0.93159 (11)0.073 (3)
H350.12990.64780.94520.087*
C360.0618 (13)0.5657 (5)0.92750 (11)0.055 (2)
C370.0811 (11)0.5221 (4)0.90715 (11)0.0486 (18)
H370.19970.48720.90400.058*
C380.0668 (11)0.5280 (4)0.89134 (10)0.0482 (19)
H380.04740.49860.87740.058*
O390.2111 (7)0.5509 (3)0.94215 (7)0.0571 (14)
C400.1781 (11)0.5796 (5)0.96488 (10)0.058 (2)
H400.03240.57200.96850.070*
C410.2355 (12)0.6816 (6)0.96782 (11)0.065 (2)
H41A0.16350.72000.95670.078*
H41B0.18990.70280.98250.078*
C420.4608 (13)0.7012 (6)0.96576 (12)0.067 (2)
H420.50270.68290.95050.080*
C430.5725 (12)0.6362 (5)0.98192 (11)0.068 (2)
H43A0.71900.64680.98050.082*
H43B0.53290.65250.99720.082*
C440.5252 (11)0.5309 (5)0.97753 (11)0.062 (2)
H44A0.59830.49100.98830.075*
H44B0.57230.51360.96260.075*
C450.3010 (12)0.5114 (5)0.97933 (11)0.058 (2)
H450.26240.52470.99490.070*
C460.5138 (15)0.8043 (5)0.96894 (12)0.097 (3)
H46A0.45260.84200.95720.145*
H46B0.46310.82590.98320.145*
H46C0.66010.81180.96850.145*
C470.2482 (12)0.4076 (6)0.97495 (12)0.069 (2)
H470.29590.39180.95980.083*
C480.3554 (13)0.3398 (5)0.99113 (12)0.092 (3)
H48A0.32720.35961.00630.138*
H48B0.30640.27500.98890.138*
H48C0.50060.34190.98850.138*
C490.0199 (12)0.3867 (6)0.97584 (12)0.095 (3)
H49A0.00190.31790.97560.142*
H49B0.03660.41310.98940.142*
H49C0.04630.41570.96310.142*
C500.9513 (12)0.5551 (5)0.81750 (10)0.0484 (19)
C510.7809 (12)0.5539 (5)0.80502 (10)0.055 (2)
H510.67340.59550.80850.067*
C520.7629 (12)0.4924 (5)0.78727 (11)0.061 (2)
H520.64470.49210.77850.074*
C530.9192 (13)0.4324 (5)0.78265 (10)0.058 (2)
C541.0923 (12)0.4314 (5)0.79545 (10)0.054 (2)
H541.19810.38830.79230.065*
C551.1079 (12)0.4943 (5)0.81291 (10)0.057 (2)
H551.22610.49540.82170.068*
O560.9187 (8)0.3675 (3)0.76562 (8)0.0770 (16)
C570.7784 (13)0.3828 (6)0.74747 (12)0.076 (3)
H570.64400.40110.75350.091*
C580.8550 (16)0.4602 (7)0.73252 (15)0.096 (3)
H58A0.86850.51940.74120.116*
H58B0.75450.47170.72080.116*
C591.056 (2)0.4378 (8)0.72183 (17)0.124 (4)
H591.15520.42960.73410.148*0.60
H59A1.17290.44240.73210.148*0.40
C601.0396 (18)0.3423 (9)0.71027 (18)0.146 (5)
H60A0.94730.34880.69760.175*
H60B1.17340.32460.70450.175*
C610.9646 (15)0.2633 (7)0.72493 (16)0.105 (4)
H61A1.06570.25050.73650.126*
H61B0.94900.20480.71610.126*
C620.7627 (13)0.2874 (7)0.73586 (14)0.083 (3)
H620.66270.29530.72370.099*
C631.146 (4)0.5107 (17)0.7059 (4)0.131 (9)0.60
H63A1.17170.57020.71380.196*0.60
H63B1.05190.52240.69380.196*0.60
H63C1.27290.48630.70000.196*0.60
C63A1.041 (6)0.523 (3)0.7052 (7)0.16 (2)0.40
H63D1.17420.53540.69890.246*0.40
H63E0.99270.57920.71290.246*0.40
H63F0.94750.50620.69330.246*0.40
C640.6838 (16)0.2073 (6)0.75075 (14)0.089 (3)
H640.78440.19810.76280.107*
C650.4891 (16)0.2355 (8)0.76140 (16)0.145 (5)
H65A0.39600.25880.75010.217*
H65B0.51410.28570.77220.217*
H65C0.43000.18040.76880.217*
C660.6701 (18)0.1141 (6)0.73813 (16)0.144 (5)
H66A0.61100.12570.72360.216*
H66B0.58560.06940.74630.216*
H66C0.80500.08730.73640.216*
C1L0.8008 (15)1.0207 (6)0.94351 (13)0.094 (3)
H1L0.73160.97560.93330.113*0.50
H1LA0.76390.97400.93180.113*0.50
Cl10.647 (2)1.0539 (12)0.96442 (17)0.140 (4)0.50
Cl1A0.569 (3)1.0590 (13)0.95422 (18)0.156 (5)0.50
Cl20.9810 (6)0.9642 (2)0.95867 (5)0.1786 (16)
Cl30.8989 (7)1.1142 (2)0.92953 (5)0.1788 (16)
O2L0.5211 (11)0.7631 (6)0.82855 (13)0.168 (3)
H2L0.39960.74790.82730.252*
C3L0.5371 (17)0.8457 (10)0.8417 (2)0.171 (6)
H3LA0.67940.86410.84370.205*
H3LB0.47550.83540.85640.205*
C4L0.4265 (19)0.9186 (9)0.82927 (17)0.159 (5)
H4LB0.45070.90980.81350.238*
H4LC0.47300.98170.83370.238*
H4LD0.28240.91270.83230.238*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (5)0.044 (4)0.050 (4)0.003 (4)0.004 (4)0.000 (4)
N20.062 (4)0.050 (4)0.059 (4)0.012 (4)0.005 (3)0.013 (3)
N30.057 (4)0.050 (4)0.061 (4)0.015 (4)0.011 (3)0.008 (3)
C40.050 (6)0.050 (5)0.045 (4)0.004 (4)0.001 (4)0.010 (4)
N50.047 (4)0.036 (3)0.047 (3)0.016 (3)0.006 (3)0.003 (3)
C60.042 (5)0.048 (4)0.054 (4)0.005 (4)0.009 (4)0.014 (4)
N70.052 (4)0.050 (4)0.050 (3)0.006 (4)0.001 (3)0.000 (3)
N80.065 (5)0.055 (4)0.050 (3)0.015 (4)0.000 (4)0.002 (3)
C90.059 (6)0.041 (4)0.041 (4)0.007 (4)0.001 (4)0.002 (3)
N100.048 (4)0.038 (4)0.048 (3)0.002 (3)0.010 (3)0.005 (3)
N120.056 (5)0.057 (4)0.057 (4)0.007 (4)0.004 (3)0.004 (3)
N130.059 (5)0.050 (4)0.055 (4)0.009 (4)0.006 (3)0.006 (3)
C110.061 (6)0.040 (4)0.046 (4)0.010 (4)0.004 (4)0.008 (4)
C140.055 (5)0.035 (4)0.053 (4)0.009 (4)0.000 (4)0.002 (3)
N150.048 (4)0.043 (4)0.045 (3)0.003 (3)0.000 (3)0.010 (3)
C160.054 (6)0.043 (5)0.054 (4)0.009 (5)0.007 (4)0.007 (4)
C170.073 (6)0.073 (6)0.090 (6)0.006 (6)0.014 (5)0.021 (5)
C180.070 (6)0.065 (6)0.076 (5)0.027 (6)0.019 (5)0.027 (4)
C190.056 (6)0.048 (5)0.069 (5)0.001 (5)0.005 (5)0.003 (4)
C200.042 (5)0.061 (5)0.097 (6)0.011 (5)0.019 (4)0.016 (5)
C210.061 (6)0.053 (5)0.089 (6)0.001 (5)0.005 (5)0.022 (4)
O220.052 (3)0.041 (3)0.084 (3)0.008 (3)0.006 (3)0.005 (3)
C230.057 (6)0.040 (4)0.080 (5)0.000 (4)0.003 (5)0.004 (4)
C240.050 (6)0.047 (5)0.108 (7)0.000 (4)0.012 (5)0.002 (5)
C250.074 (7)0.056 (5)0.091 (6)0.003 (6)0.019 (6)0.005 (5)
C260.091 (8)0.078 (7)0.130 (9)0.019 (7)0.023 (7)0.010 (6)
C270.061 (6)0.064 (6)0.128 (8)0.023 (5)0.008 (6)0.020 (6)
C280.060 (6)0.048 (5)0.110 (7)0.007 (5)0.001 (6)0.022 (5)
C290.133 (9)0.098 (7)0.098 (7)0.004 (7)0.006 (7)0.042 (6)
C300.066 (7)0.069 (6)0.121 (8)0.001 (6)0.003 (6)0.017 (6)
C310.129 (10)0.127 (9)0.098 (7)0.005 (8)0.018 (8)0.024 (6)
C320.093 (8)0.108 (8)0.180 (10)0.010 (7)0.042 (7)0.057 (7)
C330.054 (5)0.051 (5)0.048 (4)0.009 (4)0.010 (4)0.003 (4)
C340.062 (6)0.106 (7)0.051 (4)0.040 (5)0.007 (4)0.001 (5)
C350.055 (6)0.115 (7)0.048 (4)0.041 (6)0.000 (4)0.018 (4)
C360.067 (6)0.052 (5)0.045 (4)0.003 (5)0.006 (4)0.002 (4)
C370.036 (4)0.044 (4)0.066 (5)0.011 (4)0.004 (4)0.004 (4)
C380.058 (5)0.039 (4)0.047 (4)0.019 (4)0.007 (4)0.000 (3)
O390.044 (3)0.077 (4)0.051 (3)0.022 (3)0.007 (3)0.006 (3)
C400.054 (5)0.077 (6)0.043 (4)0.018 (5)0.002 (4)0.003 (4)
C410.063 (6)0.076 (6)0.055 (5)0.023 (5)0.000 (4)0.001 (4)
C420.071 (7)0.071 (6)0.058 (5)0.020 (6)0.000 (5)0.001 (4)
C430.060 (6)0.078 (6)0.067 (5)0.008 (5)0.008 (5)0.006 (4)
C440.039 (5)0.084 (6)0.064 (5)0.006 (5)0.002 (4)0.000 (4)
C450.066 (6)0.059 (5)0.050 (4)0.008 (5)0.008 (4)0.005 (4)
C460.140 (9)0.077 (6)0.074 (5)0.001 (7)0.012 (6)0.003 (5)
C470.061 (6)0.084 (7)0.061 (5)0.014 (6)0.005 (5)0.014 (5)
C480.100 (8)0.077 (6)0.098 (6)0.013 (6)0.014 (6)0.020 (5)
C490.064 (7)0.121 (8)0.100 (6)0.006 (6)0.004 (5)0.014 (6)
C500.058 (6)0.042 (4)0.045 (4)0.002 (4)0.002 (4)0.005 (3)
C510.053 (6)0.064 (5)0.050 (4)0.008 (5)0.005 (4)0.001 (4)
C520.072 (6)0.063 (5)0.048 (4)0.006 (5)0.009 (4)0.006 (4)
C530.068 (6)0.057 (5)0.049 (4)0.004 (5)0.013 (5)0.015 (4)
C540.065 (6)0.049 (4)0.048 (4)0.015 (5)0.003 (4)0.013 (4)
C550.056 (6)0.063 (5)0.051 (4)0.008 (5)0.001 (4)0.006 (4)
O560.075 (4)0.084 (4)0.071 (3)0.020 (4)0.016 (3)0.034 (3)
C570.081 (7)0.076 (6)0.070 (5)0.026 (6)0.015 (5)0.028 (5)
C580.125 (10)0.090 (7)0.075 (6)0.001 (8)0.018 (6)0.020 (6)
C590.150 (12)0.119 (9)0.101 (8)0.034 (10)0.024 (8)0.050 (7)
C600.117 (10)0.175 (12)0.145 (11)0.022 (10)0.022 (9)0.075 (10)
C610.078 (8)0.105 (9)0.133 (9)0.023 (7)0.021 (7)0.078 (7)
C620.067 (7)0.099 (8)0.082 (6)0.012 (6)0.020 (5)0.045 (6)
C630.141 (18)0.139 (16)0.113 (14)0.047 (13)0.034 (13)0.021 (11)
C63A0.15 (3)0.18 (3)0.16 (2)0.012 (18)0.014 (18)0.003 (18)
C640.114 (9)0.078 (7)0.076 (6)0.002 (7)0.037 (6)0.016 (5)
C650.118 (10)0.176 (12)0.139 (9)0.018 (10)0.041 (8)0.019 (8)
C660.189 (13)0.088 (7)0.154 (9)0.020 (9)0.040 (9)0.047 (7)
C1L0.148 (10)0.076 (6)0.059 (5)0.011 (7)0.006 (6)0.004 (5)
Cl10.182 (11)0.114 (6)0.124 (8)0.015 (7)0.046 (7)0.032 (7)
Cl1A0.221 (15)0.121 (6)0.126 (9)0.005 (9)0.050 (8)0.009 (8)
Cl20.229 (4)0.172 (3)0.135 (2)0.016 (3)0.078 (3)0.038 (2)
Cl30.278 (5)0.113 (2)0.145 (2)0.014 (3)0.074 (3)0.048 (2)
O2L0.093 (6)0.203 (9)0.208 (8)0.003 (7)0.045 (6)0.001 (7)
C3L0.086 (9)0.165 (11)0.261 (13)0.054 (8)0.082 (9)0.100 (10)
C4L0.130 (11)0.202 (13)0.144 (10)0.021 (12)0.033 (9)0.007 (9)
Geometric parameters (Å, º) top
C1—N21.317 (8)C42—H421.0000
C1—N151.381 (7)C43—C441.541 (8)
C1—C161.456 (9)C43—H43A0.9900
N2—N31.413 (7)C43—H43B0.9900
N3—C41.286 (7)C44—C451.521 (9)
C4—N51.370 (8)C44—H44A0.9900
C4—N151.387 (8)C44—H44B0.9900
N5—C91.369 (7)C45—C471.527 (9)
N5—C61.413 (8)C45—H451.0000
C6—N71.293 (7)C46—H46A0.9800
C6—C331.472 (9)C46—H46B0.9800
N7—N81.398 (7)C46—H46C0.9800
N8—C91.287 (8)C47—C481.546 (9)
C9—N101.388 (8)C47—C491.549 (10)
N10—C141.374 (7)C47—H471.0000
N10—C111.398 (8)C48—H48A0.9800
N12—C111.291 (8)C48—H48B0.9800
N12—N131.415 (7)C48—H48C0.9800
N13—C141.292 (8)C49—H49A0.9800
C11—C501.471 (8)C49—H49B0.9800
C14—N151.372 (8)C49—H49C0.9800
C16—C171.373 (9)C50—C511.364 (9)
C16—C211.373 (9)C50—C551.378 (9)
C17—C181.368 (9)C51—C521.388 (8)
C17—H170.9500C51—H510.9500
C18—C191.369 (9)C52—C531.370 (9)
C18—H180.9500C52—H520.9500
C19—C201.358 (9)C53—O561.382 (7)
C19—O221.369 (8)C53—C541.390 (9)
C20—C211.398 (9)C54—C551.386 (8)
C20—H200.9500C54—H540.9500
C21—H210.9500C55—H550.9500
O22—C231.466 (7)O56—C571.461 (8)
C23—C241.494 (9)C57—C581.508 (10)
C23—C281.526 (9)C57—C621.523 (10)
C23—H231.0000C57—H571.0000
C24—C251.514 (9)C58—C591.521 (13)
C24—H24A0.9900C58—H58A0.9900
C24—H24B0.9900C58—H58B0.9900
C25—C261.507 (10)C59—C601.523 (12)
C25—C291.522 (10)C59—C631.533 (15)
C25—H251.0000C59—C63A1.569 (19)
C26—C271.514 (10)C59—H591.0000
C26—H26A0.9900C59—H59A1.0000
C26—H26B0.9900C60—C611.511 (12)
C27—C281.547 (10)C60—H60A0.9900
C27—H27A0.9900C60—H60B0.9900
C27—H27B0.9900C61—C621.537 (11)
C28—C301.520 (10)C61—H61A0.9900
C28—H281.0000C61—H61B0.9900
C29—H29A0.9800C62—C641.540 (11)
C29—H29B0.9800C62—H621.0000
C29—H29C0.9800C63—H63A0.9800
C30—C311.517 (10)C63—H63B0.9800
C30—C321.588 (11)C63—H63C0.9800
C30—H301.0000C63A—H63D0.9800
C31—H31A0.9800C63A—H63E0.9800
C31—H31B0.9800C63A—H63F0.9800
C31—H31C0.9800C64—C651.502 (11)
C32—H32A0.9800C64—C661.524 (10)
C32—H32B0.9800C64—H641.0000
C32—H32C0.9800C65—H65A0.9800
C33—C341.374 (8)C65—H65B0.9800
C33—C381.382 (8)C65—H65C0.9800
C34—C351.396 (9)C66—H66A0.9800
C34—H340.9500C66—H66B0.9800
C35—C361.383 (9)C66—H66C0.9800
C35—H350.9500C1L—Cl31.698 (8)
C36—O391.350 (8)C1L—Cl11.699 (18)
C36—C371.387 (8)C1L—Cl21.710 (9)
C37—C381.378 (8)C1L—Cl1A1.76 (2)
C37—H370.9500C1L—H1L1.0000
C38—H380.9500C1L—H1LA1.0000
O39—C401.456 (7)O2L—C3L1.418 (11)
C40—C411.498 (9)O2L—H2L0.8400
C40—C451.538 (9)C3L—C4L1.474 (13)
C40—H401.0000C3L—H3LA0.9900
C41—C421.530 (10)C3L—H3LB0.9900
C41—H41A0.9900C4L—H4LB0.9800
C41—H41B0.9900C4L—H4LC0.9800
C42—C461.507 (9)C4L—H4LD0.9800
C42—C431.536 (9)
N2—C1—N15107.9 (6)C44—C43—H43B109.3
N2—C1—C16126.0 (7)H43A—C43—H43B108.0
N15—C1—C16125.4 (6)C45—C44—C43111.3 (7)
C1—N2—N3109.0 (5)C45—C44—H44A109.4
C4—N3—N2106.5 (6)C43—C44—H44A109.4
N3—C4—N5133.0 (7)C45—C44—H44B109.4
N3—C4—N15110.8 (6)C43—C44—H44B109.4
N5—C4—N15116.2 (6)H44A—C44—H44B108.0
C9—N5—C4123.1 (6)C44—C45—C47112.7 (7)
C9—N5—C6101.8 (5)C44—C45—C40111.5 (6)
C4—N5—C6134.8 (6)C47—C45—C40112.2 (6)
N7—C6—N5109.5 (6)C44—C45—H45106.6
N7—C6—C33121.4 (7)C47—C45—H45106.6
N5—C6—C33129.2 (7)C40—C45—H45106.6
C6—N7—N8109.5 (6)C42—C46—H46A109.5
C9—N8—N7104.9 (6)C42—C46—H46B109.5
N8—C9—N5114.3 (7)H46A—C46—H46B109.5
N8—C9—N10127.9 (7)C42—C46—H46C109.5
N5—C9—N10117.7 (6)H46A—C46—H46C109.5
C14—N10—C9122.1 (6)H46B—C46—H46C109.5
C14—N10—C11104.3 (6)C45—C47—C48112.0 (6)
C9—N10—C11133.3 (6)C45—C47—C49113.7 (7)
C11—N12—N13110.3 (6)C48—C47—C49108.2 (7)
C14—N13—N12104.6 (6)C45—C47—H47107.5
N12—C11—N10108.2 (6)C48—C47—H47107.5
N12—C11—C50126.2 (7)C49—C47—H47107.5
N10—C11—C50125.3 (7)C47—C48—H48A109.5
N13—C14—N15130.6 (7)C47—C48—H48B109.5
N13—C14—N10112.6 (6)H48A—C48—H48B109.5
N15—C14—N10116.8 (7)C47—C48—H48C109.5
C14—N15—C1130.5 (6)H48A—C48—H48C109.5
C14—N15—C4123.8 (6)H48B—C48—H48C109.5
C1—N15—C4105.7 (6)C47—C49—H49A109.5
C17—C16—C21118.9 (8)C47—C49—H49B109.5
C17—C16—C1119.5 (8)H49A—C49—H49B109.5
C21—C16—C1121.6 (7)C47—C49—H49C109.5
C18—C17—C16121.4 (8)H49A—C49—H49C109.5
C18—C17—H17119.3H49B—C49—H49C109.5
C16—C17—H17119.3C51—C50—C55120.5 (7)
C17—C18—C19120.1 (8)C51—C50—C11120.7 (7)
C17—C18—H18120.0C55—C50—C11118.6 (7)
C19—C18—H18120.0C50—C51—C52120.8 (7)
C20—C19—O22115.7 (8)C50—C51—H51119.6
C20—C19—C18119.3 (8)C52—C51—H51119.6
O22—C19—C18124.9 (7)C53—C52—C51118.6 (7)
C19—C20—C21121.0 (8)C53—C52—H52120.7
C19—C20—H20119.5C51—C52—H52120.7
C21—C20—H20119.5C52—C53—O56124.1 (7)
C16—C21—C20119.3 (7)C52—C53—C54121.4 (6)
C16—C21—H21120.4O56—C53—C54114.5 (7)
C20—C21—H21120.4C55—C54—C53118.9 (7)
C19—O22—C23117.7 (6)C55—C54—H54120.5
O22—C23—C24110.2 (6)C53—C54—H54120.5
O22—C23—C28105.1 (6)C50—C55—C54119.8 (7)
C24—C23—C28112.7 (6)C50—C55—H55120.1
O22—C23—H23109.6C54—C55—H55120.1
C24—C23—H23109.6C53—O56—C57118.0 (6)
C28—C23—H23109.6O56—C57—C58110.2 (8)
C23—C24—C25114.2 (7)O56—C57—C62105.2 (6)
C23—C24—H24A108.7C58—C57—C62112.6 (7)
C25—C24—H24A108.7O56—C57—H57109.6
C23—C24—H24B108.7C58—C57—H57109.6
C25—C24—H24B108.7C62—C57—H57109.6
H24A—C24—H24B107.6C57—C58—C59113.9 (9)
C26—C25—C24108.2 (7)C57—C58—H58A108.8
C26—C25—C29110.2 (7)C59—C58—H58A108.8
C24—C25—C29111.7 (7)C57—C58—H58B108.8
C26—C25—H25108.9C59—C58—H58B108.8
C24—C25—H25108.9H58A—C58—H58B107.7
C29—C25—H25108.9C58—C59—C60108.5 (10)
C25—C26—C27111.2 (7)C58—C59—C63118.3 (16)
C25—C26—H26A109.4C60—C59—C63109.3 (14)
C27—C26—H26A109.4C58—C59—C63A93.5 (19)
C25—C26—H26B109.4C60—C59—C63A112 (2)
C27—C26—H26B109.4C58—C59—H59106.7
H26A—C26—H26B108.0C60—C59—H59106.7
C26—C27—C28113.9 (8)C63—C59—H59106.7
C26—C27—H27A108.8C63A—C59—H59127.5
C28—C27—H27A108.8C58—C59—H59A113.7
C26—C27—H27B108.8C60—C59—H59A113.7
C28—C27—H27B108.8C63—C59—H59A92.6
H27A—C27—H27B107.7C63A—C59—H59A113.7
C30—C28—C23112.3 (7)C61—C60—C59113.8 (9)
C30—C28—C27115.3 (8)C61—C60—H60A108.8
C23—C28—C27108.0 (6)C59—C60—H60A108.8
C30—C28—H28106.9C61—C60—H60B108.8
C23—C28—H28106.9C59—C60—H60B108.8
C27—C28—H28106.9H60A—C60—H60B107.7
C25—C29—H29A109.5C60—C61—C62112.4 (9)
C25—C29—H29B109.5C60—C61—H61A109.1
H29A—C29—H29B109.5C62—C61—H61A109.1
C25—C29—H29C109.5C60—C61—H61B109.1
H29A—C29—H29C109.5C62—C61—H61B109.1
H29B—C29—H29C109.5H61A—C61—H61B107.9
C31—C30—C28113.7 (8)C57—C62—C61109.6 (8)
C31—C30—C32108.7 (8)C57—C62—C64113.6 (7)
C28—C30—C32109.4 (7)C61—C62—C64112.9 (9)
C31—C30—H30108.3C57—C62—H62106.8
C28—C30—H30108.3C61—C62—H62106.8
C32—C30—H30108.3C64—C62—H62106.8
C30—C31—H31A109.5C59—C63—H63A109.5
C30—C31—H31B109.5C59—C63—H63B109.5
H31A—C31—H31B109.5C59—C63—H63C109.5
C30—C31—H31C109.5C59—C63A—H63D109.5
H31A—C31—H31C109.5C59—C63A—H63E109.5
H31B—C31—H31C109.5H63D—C63A—H63E109.5
C30—C32—H32A109.5C59—C63A—H63F109.5
C30—C32—H32B109.5H63D—C63A—H63F109.5
H32A—C32—H32B109.5H63E—C63A—H63F109.5
C30—C32—H32C109.5C65—C64—C66113.2 (10)
H32A—C32—H32C109.5C65—C64—C62110.7 (8)
H32B—C32—H32C109.5C66—C64—C62110.9 (8)
C34—C33—C38118.3 (7)C65—C64—H64107.3
C34—C33—C6122.5 (7)C66—C64—H64107.3
C38—C33—C6119.1 (6)C62—C64—H64107.3
C33—C34—C35121.3 (7)C64—C65—H65A109.5
C33—C34—H34119.3C64—C65—H65B109.5
C35—C34—H34119.3H65A—C65—H65B109.5
C36—C35—C34120.3 (7)C64—C65—H65C109.5
C36—C35—H35119.8H65A—C65—H65C109.5
C34—C35—H35119.8H65B—C65—H65C109.5
O39—C36—C35125.5 (6)C64—C66—H66A109.5
O39—C36—C37116.8 (7)C64—C66—H66B109.5
C35—C36—C37117.6 (7)H66A—C66—H66B109.5
C38—C37—C36121.9 (7)C64—C66—H66C109.5
C38—C37—H37119.0H66A—C66—H66C109.5
C36—C37—H37119.0H66B—C66—H66C109.5
C37—C38—C33120.4 (6)Cl3—C1L—Cl1113.1 (8)
C37—C38—H38119.8Cl3—C1L—Cl2111.2 (6)
C33—C38—H38119.8Cl1—C1L—Cl298.6 (6)
C36—O39—C40118.1 (5)Cl3—C1L—Cl1A106.5 (7)
O39—C40—C41110.0 (6)Cl2—C1L—Cl1A124.0 (6)
O39—C40—C45106.7 (6)Cl3—C1L—H1L111.1
C41—C40—C45113.4 (6)Cl1—C1L—H1L111.1
O39—C40—H40108.9Cl2—C1L—H1L111.1
C41—C40—H40108.9Cl1A—C1L—H1L91.2
C45—C40—H40108.9Cl3—C1L—H1LA104.4
C40—C41—C42114.5 (7)Cl1—C1L—H1LA124.4
C40—C41—H41A108.6Cl2—C1L—H1LA104.4
C42—C41—H41A108.6Cl1A—C1L—H1LA104.4
C40—C41—H41B108.6C3L—O2L—H2L109.5
C42—C41—H41B108.6O2L—C3L—C4L104.2 (10)
H41A—C41—H41B107.6O2L—C3L—H3LA110.9
C46—C42—C41113.2 (8)C4L—C3L—H3LA110.9
C46—C42—C43112.4 (7)O2L—C3L—H3LB110.9
C41—C42—C43108.3 (6)C4L—C3L—H3LB110.9
C46—C42—H42107.6H3LA—C3L—H3LB108.9
C41—C42—H42107.6C3L—C4L—H4LB109.5
C43—C42—H42107.6C3L—C4L—H4LC109.5
C42—C43—C44111.4 (6)H4LB—C4L—H4LC109.5
C42—C43—H43A109.3C3L—C4L—H4LD109.5
C44—C43—H43A109.3H4LB—C4L—H4LD109.5
C42—C43—H43B109.3H4LC—C4L—H4LD109.5
N15—C1—N2—N31.0 (7)C24—C23—C28—C2751.1 (8)
C16—C1—N2—N3170.1 (7)C26—C27—C28—C30179.2 (7)
C1—N2—N3—C40.8 (8)C26—C27—C28—C2352.7 (9)
N2—N3—C4—N5177.7 (7)C23—C28—C30—C3152.9 (9)
N2—N3—C4—N152.2 (7)C27—C28—C30—C31177.3 (7)
N3—C4—N5—C9176.0 (7)C23—C28—C30—C32174.7 (6)
N15—C4—N5—C93.9 (9)C27—C28—C30—C3261.0 (9)
N3—C4—N5—C62.1 (13)N7—C6—C33—C34159.3 (7)
N15—C4—N5—C6177.8 (6)N5—C6—C33—C3419.8 (11)
C9—N5—C6—N71.2 (7)N7—C6—C33—C3817.2 (10)
C4—N5—C6—N7176.0 (6)N5—C6—C33—C38163.7 (6)
C9—N5—C6—C33179.6 (6)C38—C33—C34—C352.4 (11)
C4—N5—C6—C334.8 (11)C6—C33—C34—C35179.0 (7)
N5—C6—N7—N80.6 (7)C33—C34—C35—C363.6 (12)
C33—C6—N7—N8179.9 (6)C34—C35—C36—O39173.5 (7)
C6—N7—N8—C90.2 (7)C34—C35—C36—C372.0 (12)
N7—N8—C9—N51.1 (8)O39—C36—C37—C38176.4 (6)
N7—N8—C9—N10179.3 (6)C35—C36—C37—C380.5 (10)
C4—N5—C9—N8177.1 (6)C36—C37—C38—C331.6 (10)
C6—N5—C9—N81.5 (7)C34—C33—C38—C370.1 (10)
C4—N5—C9—N104.6 (9)C6—C33—C38—C37176.6 (6)
C6—N5—C9—N10179.8 (5)C35—C36—O39—C407.4 (11)
N8—C9—N10—C14178.0 (7)C37—C36—O39—C40168.2 (6)
N5—C9—N10—C140.1 (9)C36—O39—C40—C4187.0 (8)
N8—C9—N10—C116.1 (12)C36—O39—C40—C45149.7 (6)
N5—C9—N10—C11172.0 (6)O39—C40—C41—C4268.3 (8)
C11—N12—N13—C140.8 (8)C45—C40—C41—C4251.0 (8)
N13—N12—C11—N100.7 (8)C40—C41—C42—C46179.6 (6)
N13—N12—C11—C50176.1 (6)C40—C41—C42—C4354.4 (8)
C14—N10—C11—N120.3 (7)C46—C42—C43—C44176.8 (7)
C9—N10—C11—N12173.2 (6)C41—C42—C43—C4457.5 (8)
C14—N10—C11—C50175.7 (6)C42—C43—C44—C4558.5 (8)
C9—N10—C11—C5011.3 (11)C43—C44—C45—C47179.7 (5)
N12—N13—C14—N15179.1 (6)C43—C44—C45—C4052.5 (8)
N12—N13—C14—N100.7 (7)O39—C40—C45—C4472.3 (7)
C9—N10—C14—N13173.6 (6)C41—C40—C45—C4448.9 (8)
C11—N10—C14—N130.3 (7)O39—C40—C45—C4755.3 (8)
C9—N10—C14—N155.1 (9)C41—C40—C45—C47176.5 (6)
C11—N10—C14—N15179.0 (5)C44—C45—C47—C4859.1 (8)
N13—C14—N15—C19.1 (12)C40—C45—C47—C48174.1 (6)
N10—C14—N15—C1172.5 (6)C44—C45—C47—C49177.9 (6)
N13—C14—N15—C4172.5 (7)C40—C45—C47—C4951.0 (9)
N10—C14—N15—C45.9 (9)N12—C11—C50—C51124.7 (8)
N2—C1—N15—C14179.2 (6)N10—C11—C50—C5149.9 (10)
C16—C1—N15—C149.7 (11)N12—C11—C50—C5550.6 (10)
N2—C1—N15—C42.2 (7)N10—C11—C50—C55134.7 (7)
C16—C1—N15—C4168.9 (7)C55—C50—C51—C521.0 (10)
N3—C4—N15—C14178.5 (6)C11—C50—C51—C52174.3 (6)
N5—C4—N15—C141.6 (9)C50—C51—C52—C530.6 (11)
N3—C4—N15—C12.8 (7)C51—C52—C53—O56179.3 (6)
N5—C4—N15—C1177.1 (5)C51—C52—C53—C540.7 (11)
N2—C1—C16—C1780.2 (9)C52—C53—C54—C551.6 (11)
N15—C1—C16—C1789.3 (9)O56—C53—C54—C55179.7 (6)
N2—C1—C16—C2199.0 (9)C51—C50—C55—C540.0 (10)
N15—C1—C16—C2191.5 (9)C11—C50—C55—C54175.3 (6)
C21—C16—C17—C180.7 (12)C53—C54—C55—C501.2 (10)
C1—C16—C17—C18180.0 (7)C52—C53—O56—C5720.5 (11)
C16—C17—C18—C190.1 (12)C54—C53—O56—C57160.8 (7)
C17—C18—C19—C201.0 (12)C53—O56—C57—C5876.7 (8)
C17—C18—C19—O22177.0 (7)C53—O56—C57—C62161.7 (7)
O22—C19—C20—C21177.0 (6)O56—C57—C58—C5961.5 (9)
C18—C19—C20—C211.1 (12)C62—C57—C58—C5955.7 (10)
C17—C16—C21—C200.6 (11)C57—C58—C59—C6053.6 (11)
C1—C16—C21—C20179.8 (7)C57—C58—C59—C63178.8 (14)
C19—C20—C21—C160.3 (12)C57—C58—C59—C63A168 (2)
C20—C19—O22—C23153.4 (6)C58—C59—C60—C6153.4 (13)
C18—C19—O22—C2328.6 (10)C63—C59—C60—C61176.3 (15)
C19—O22—C23—C2466.4 (8)C63A—C59—C60—C61155 (2)
C19—O22—C23—C28172.0 (6)C59—C60—C61—C6255.0 (13)
O22—C23—C24—C2560.7 (8)O56—C57—C62—C6167.1 (9)
C28—C23—C24—C2556.3 (8)C58—C57—C62—C6152.9 (10)
C23—C24—C25—C2656.9 (9)O56—C57—C62—C6460.2 (9)
C23—C24—C25—C29178.3 (7)C58—C57—C62—C64179.7 (8)
C24—C25—C26—C2756.0 (9)C60—C61—C62—C5752.6 (10)
C29—C25—C26—C27178.4 (7)C60—C61—C62—C64179.7 (8)
C25—C26—C27—C2857.3 (9)C57—C62—C64—C6553.1 (10)
O22—C23—C28—C3059.3 (8)C61—C62—C64—C65178.7 (7)
C24—C23—C28—C30179.3 (7)C57—C62—C64—C66179.5 (8)
O22—C23—C28—C2768.9 (8)C61—C62—C64—C6654.9 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2L—H2L···N12i0.842.112.896 (10)156
Symmetry code: (i) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2L—H2L···N12i0.842.112.896 (10)155.7
Symmetry code: (i) x1, y, z.
Acknowledgements top

The authors are grateful to Heinz Kolshorn for helpful discussions.

references
References top

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