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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2005.
Published online 2008 September 24. doi:  10.1107/S1600536808030365
PMCID: PMC2959420

1-{Phen­yl[1-(p-tol­yl)ethyl­amino]meth­yl}-2-naphthol

Abstract

The title compound, C26H25NO, was obtained via a one-pot synthesis from the reaction of 2-naphthol, 1-(p-tol­yl)ethyl­amine, p-toluene­sulfonic acid and benzaldehyde. There are three mol­ecules per asymmetric unit, all having similar conformations. There are intra­molecular O—H(...)N and C—H(...)O hydrogen bonds, with only van der Waals forces found between mol­ecules.

Related literature

For background, see: Devi & Bhuyan (2004 [triangle]); Domling & Ugi (2000 [triangle]); Hulme & Gore (2003 [triangle]); Ugi (1962 [triangle]). For related literature, see: Liu et al. (2001 [triangle]).

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Object name is e-64-o2005-scheme1.jpg

Experimental

Crystal data

  • C26H25NO
  • M r = 367.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2005-efi1.jpg
  • a = 9.3046 (19) Å
  • b = 13.126 (3) Å
  • c = 13.572 (3) Å
  • α = 88.14 (3)°
  • β = 89.99 (2)°
  • γ = 72.39 (3)°
  • V = 1579.0 (5) Å3
  • Z = 3
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 292 (2) K
  • 0.50 × 0.40 × 0.30 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.950, T max = 0.980
  • 16610 measured reflections
  • 7208 independent reflections
  • 4449 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.136
  • S = 1.05
  • 7208 reflections
  • 760 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL/PC (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL/PC.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030365/fl2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030365/fl2220Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Yong-Hua Li.

supplementary crystallographic information

Comment

Multi-component reactions (MCRs) (Hulme & Gore, 2003; Ugi,1962) involving at least three starting materials in a one-pot reaction have attracted considerable attention in terms of saving both energy and raw materials (Devi & Bhuyan, 2004). Compared to conventional multi-step organic syntheses, MCRs have merits over multi-step reactions that include the simplicity of a one-pot procedure and the buildup of complex molecules (Domling & Ugi, 2000). Here we report the synthesis and crystal structure of the title compound (I, Fig. 1), obtained by a four-component condensation reaction as described in the experimental section.

I is an optically active derivative that crystallized with three molecules per asymmetric unit which is very rare. A few examples of similar compounds which contain two molecules per asymmetric unit have been reported (Liu et al., 2001).

All three molecules in the asymmetric unit have the same relative conformation for both chiral carbon atoms. The dihedral angles between the rings A (C1–C6), B (C8–C17) and C (C20–C25) are A/B =71.90°, B/C =20.28°. The dihedral angles between the rings D (C38–C43), E (C27–C36) and F (C46–C51) are D/E =73.62°, E/F = 45.16° and the dihedral angles between the rings G (C64–C69), H (C53–C62) and I (C72–C77) are G/H =77.41°, H/I =62.04°. The three molecules are all stabilized by intramolecular O—H···N hydrogen bonding however, only one is involved in intramolecular C—H···O hydrogen bonds, no similar C—H···O distances are found in the other two molecules (Table 1). Intermolecular attractions are only on the order of Van der Waals forces.

Experimental

Benzaldehyde (1.59 g, 0.015 mol) and p-toluenesulfonic acid (0.1 g) was added to 2-naphthol (2.16 g, 0.015 mol) without solvent. 1-(p-tolyl)ethylamine (2.025 g, 0.015 mol) was added dropwise with cooling to 0°C to the above mixture under nitrogen. The temperature was then gradually raised to 120°C over a period of hour and the mixture was stirred at this temperature for 24 h, then 20 ml of ethanol 95% was added, the precipitate was filtered and washed with a small amount of ethanol 95%. The title compound was isolated using column chromatography (Petroleum ether: ethyl acetate-5:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of an ethyl acetate solution.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2–1.5Ueq(C). In the absence of significant anomalous scattering effects, 6529 Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C26H25NOZ = 3
Mr = 367.47F(000) = 588
Triclinic, P1Dx = 1.159 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3046 (19) ÅCell parameters from 7208 reflections
b = 13.126 (3) Åθ = 3.0–27.5°
c = 13.572 (3) ŵ = 0.07 mm1
α = 88.14 (3)°T = 292 K
β = 89.99 (2)°Prism, colorless
γ = 72.39 (3)°0.50 × 0.40 × 0.30 mm
V = 1579.0 (5) Å3

Data collection

Rigaku SCXmini diffractometer7208 independent reflections
Radiation source: fine-focus sealed tube4449 reflections with I > 2σ(I)
graphiteRint = 0.048
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD p rofilefitting scansh = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −17→17
Tmin = 0.950, Tmax = 0.980l = −17→17
16610 measured reflections

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0528P] where P = (Fo2 + 2Fc2)/3
7208 reflections(Δ/σ)max < 0.001
760 parametersΔρmax = 0.15 e Å3
3 restraintsΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/Ueq
C10.3155 (4)0.7172 (3)0.8864 (3)0.0628 (9)
C20.2500 (5)0.6843 (4)0.9671 (3)0.0804 (12)
H50A0.17110.65570.95830.096*
C30.3005 (7)0.6934 (4)1.0618 (4)0.0998 (15)
H75A0.25390.67201.11580.120*
C40.4167 (7)0.7332 (4)1.0759 (4)0.0918 (15)
H67A0.45230.73671.13940.110*
C50.4819 (6)0.7682 (4)0.9965 (4)0.0867 (13)
H61A0.55930.79821.00590.104*
C60.4315 (5)0.7588 (3)0.9024 (3)0.0759 (11)
H53A0.47750.78120.84860.091*
C70.2582 (4)0.7047 (3)0.7836 (3)0.0640 (10)
H30A0.16990.67930.79130.077*
C80.2098 (5)0.8090 (3)0.7229 (3)0.0695 (10)
C90.3141 (7)0.8430 (4)0.6695 (3)0.0906 (14)
C100.2735 (11)0.9451 (6)0.6209 (4)0.116 (2)
H73A0.34600.96750.58710.140*
C110.1332 (13)1.0083 (6)0.6237 (5)0.131 (3)
H76A0.11001.07510.59170.157*
C120.0190 (8)0.9803 (4)0.6716 (4)0.1030 (18)
C13−0.1273 (12)1.0453 (6)0.6728 (6)0.158 (4)
H81A−0.15191.11150.63950.190*
C14−0.2387 (11)1.0159 (9)0.7215 (6)0.182 (5)
H83A−0.33691.06180.72150.218*
C15−0.2030 (8)0.9166 (8)0.7711 (5)0.156 (3)
H84A−0.27810.89570.80350.187*
C16−0.0564 (6)0.8488 (5)0.7722 (4)0.1069 (17)
H72A−0.03460.78320.80620.128*
C170.0586 (6)0.8762 (4)0.7240 (3)0.0815 (13)
C180.3134 (4)0.5779 (3)0.6466 (3)0.0664 (10)
H99A0.26500.63780.60090.080*
C190.4459 (5)0.5019 (4)0.5929 (4)0.0968 (15)
H79A0.51650.53910.57390.145*
H79B0.40930.47700.53510.145*
H79C0.49510.44200.63590.145*
C200.1955 (4)0.5256 (3)0.6774 (2)0.0573 (9)
C210.0467 (5)0.5712 (3)0.6513 (3)0.0695 (10)
H54A0.01810.63460.61350.083*
C22−0.0609 (5)0.5239 (5)0.6809 (3)0.0864 (13)
H51A−0.16070.55610.66150.104*
C23−0.0267 (7)0.4327 (5)0.7369 (3)0.0868 (14)
C240.1216 (7)0.3864 (4)0.7642 (3)0.0882 (14)
H52A0.14850.32370.80310.106*
C250.2306 (5)0.4318 (3)0.7348 (3)0.0700 (10)
H27A0.33030.39870.75390.084*
C26−0.1445 (9)0.3811 (7)0.7711 (5)0.151 (3)
H10D−0.24190.42280.74630.227*
H10E−0.14610.37780.84180.227*
H10F−0.12020.31010.74680.227*
C270.0607 (4)0.6526 (3)0.3775 (2)0.0514 (8)
C280.2086 (4)0.6212 (3)0.3414 (3)0.0612 (9)
H3A0.24090.55910.30580.073*
C290.3079 (5)0.6790 (3)0.3568 (3)0.0753 (11)
H47A0.40520.65570.33200.090*
C300.2615 (6)0.7725 (4)0.4098 (3)0.0811 (12)
H44A0.32850.81100.42140.097*
C310.1192 (5)0.8072 (3)0.4444 (3)0.0746 (11)
H20A0.08930.86990.47920.090*
C320.0139 (4)0.7496 (3)0.4285 (3)0.0594 (9)
C33−0.1334 (5)0.7844 (3)0.4658 (3)0.0693 (10)
H18A−0.16370.84670.50110.083*
C34−0.2299 (5)0.7295 (3)0.4514 (3)0.0723 (11)
H35A−0.32740.75520.47540.087*
C35−0.1874 (4)0.6327 (3)0.4001 (3)0.0603 (9)
C36−0.0418 (4)0.5921 (3)0.3643 (2)0.0516 (8)
C370.0086 (4)0.4862 (3)0.3122 (3)0.0530 (8)
H6A0.11410.45080.33090.064*
C380.0010 (4)0.4984 (3)0.2004 (3)0.0514 (8)
C390.1208 (4)0.4455 (3)0.1437 (3)0.0696 (10)
H36A0.20890.40310.17450.084*
C400.1140 (5)0.4536 (4)0.0429 (3)0.0782 (11)
H80A0.19720.41780.00610.094*
C41−0.0152 (5)0.5143 (3)−0.0036 (3)0.0721 (11)
H38A−0.02010.5200−0.07200.086*
C42−0.1368 (5)0.5663 (3)0.0509 (3)0.0740 (11)
H46A−0.22530.60700.01940.089*
C43−0.1292 (4)0.5590 (3)0.1527 (3)0.0652 (10)
H57A−0.21250.59520.18930.078*
C44−0.0337 (4)0.3634 (3)0.4442 (3)0.0628 (9)
H32A−0.03080.41920.48960.075*
C45−0.1560 (5)0.3160 (4)0.4792 (4)0.0927 (14)
H56A−0.25190.37060.47680.139*
H56B−0.13430.28830.54570.139*
H56C−0.15910.25920.43730.139*
C460.1198 (4)0.2804 (3)0.4471 (2)0.0535 (8)
C470.2259 (5)0.2823 (3)0.5164 (3)0.0752 (11)
H64A0.20420.33800.56010.090*
C480.3640 (5)0.2044 (4)0.5235 (4)0.0903 (13)
H71A0.43280.20810.57190.108*
C490.4011 (5)0.1209 (4)0.4594 (3)0.0783 (12)
C500.2946 (5)0.1187 (3)0.3913 (3)0.0719 (11)
H59A0.31560.06210.34870.086*
C510.1580 (4)0.1963 (3)0.3830 (3)0.0660 (10)
H22A0.09010.19260.33400.079*
C520.5525 (6)0.0356 (5)0.4674 (5)0.129 (2)
H82A0.5590−0.01610.41790.193*
H82B0.56320.00080.53150.193*
H82C0.63150.06800.45800.193*
C530.5031 (3)0.2743 (3)0.1125 (3)0.0528 (8)
C540.4856 (4)0.2479 (3)0.2123 (3)0.0571 (8)
H4A0.46250.18520.22810.069*
C550.5015 (4)0.3117 (3)0.2868 (3)0.0658 (10)
H15A0.48810.29230.35180.079*
C560.5374 (4)0.4049 (3)0.2657 (4)0.0761 (12)
H41A0.54780.44810.31650.091*
C570.5572 (4)0.4327 (3)0.1722 (4)0.0755 (12)
H21A0.58260.49500.15900.091*
C580.5403 (4)0.3698 (3)0.0928 (3)0.0637 (9)
C590.5630 (5)0.3966 (4)−0.0060 (4)0.0822 (13)
H26A0.58900.4585−0.02030.099*
C600.5482 (5)0.3352 (4)−0.0801 (4)0.0822 (13)
H43A0.56570.3545−0.14450.099*
C610.5063 (4)0.2417 (4)−0.0614 (3)0.0675 (10)
C620.4835 (4)0.2101 (3)0.0338 (3)0.0557 (8)
C630.4476 (4)0.1062 (3)0.0570 (3)0.0576 (9)
H25A0.37930.11780.11330.069*
C640.5875 (4)0.0136 (3)0.0847 (3)0.0622 (9)
C650.5855 (6)−0.0533 (3)0.1655 (3)0.0812 (12)
H55A0.4999−0.04080.20420.097*
C660.7132 (8)−0.1398 (4)0.1884 (4)0.0960 (16)
H70A0.7131−0.18330.24390.115*
C670.8359 (7)−0.1609 (4)0.1313 (5)0.1028 (17)
H74A0.9186−0.22010.14620.123*
C680.8397 (5)−0.0961 (4)0.0522 (5)0.0941 (15)
H68A0.9257−0.11060.01360.113*
C690.7166 (5)−0.0084 (3)0.0284 (3)0.0761 (11)
H63A0.72080.0358−0.02580.091*
C700.2047 (4)0.1251 (3)−0.0320 (3)0.0685 (10)
H37A0.18600.2023−0.04230.082*
C710.1472 (6)0.0848 (5)−0.1227 (4)0.1079 (17)
H77A0.20220.0973−0.17940.162*
H77B0.04190.1221−0.13230.162*
H77C0.16110.0096−0.11410.162*
C720.1207 (4)0.1087 (3)0.0598 (3)0.0632 (9)
C730.1590 (5)0.0127 (3)0.1132 (4)0.0746 (11)
H49A0.2421−0.04250.09390.090*
C740.0789 (5)−0.0041 (3)0.1937 (4)0.0751 (11)
H48A0.1100−0.06930.22870.090*
C75−0.0481 (4)0.0753 (3)0.2232 (3)0.0671 (10)
C76−0.0865 (4)0.1706 (3)0.1707 (3)0.0699 (10)
H19A−0.17070.22520.18960.084*
C77−0.0053 (4)0.1885 (3)0.0910 (3)0.0711 (11)
H42A−0.03480.25470.05760.085*
C78−0.1366 (5)0.0563 (4)0.3107 (4)0.0927 (14)
H10A−0.0909−0.01460.33790.139*
H10B−0.23830.06390.29050.139*
H10C−0.13710.10760.35980.139*
N20.3758 (4)0.6216 (3)0.7309 (3)0.0727 (8)
H1A0.41940.56750.77390.087*
N30.3698 (4)0.0750 (3)−0.0274 (2)0.0682 (8)
H3C0.38820.0036−0.02330.082*
N1−0.0798 (3)0.4155 (2)0.3457 (2)0.0610 (7)
H4B−0.06920.36420.30150.073*
O1−0.2945 (3)0.5840 (2)0.3874 (3)0.0827 (8)
H1−0.25730.52660.36130.124*
O30.4909 (4)0.1879 (3)−0.14207 (19)0.0893 (9)
H20.44490.1453−0.12740.134*
O20.4601 (4)0.7828 (3)0.6589 (3)0.1158 (12)
H80.47400.72460.68760.174*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.069 (2)0.050 (2)0.068 (2)−0.0162 (18)−0.0044 (19)0.0020 (18)
C20.088 (3)0.083 (3)0.074 (3)−0.032 (2)−0.005 (2)0.002 (2)
C30.121 (4)0.097 (4)0.073 (3)−0.022 (3)−0.001 (3)0.007 (3)
C40.107 (4)0.069 (3)0.085 (3)−0.005 (3)−0.031 (3)−0.009 (3)
C50.087 (3)0.063 (3)0.109 (4)−0.018 (2)−0.020 (3)−0.017 (3)
C60.079 (3)0.065 (2)0.087 (3)−0.027 (2)0.001 (2)−0.009 (2)
C70.063 (2)0.050 (2)0.082 (3)−0.0216 (18)0.007 (2)−0.0088 (18)
C80.089 (3)0.069 (2)0.058 (2)−0.034 (2)0.007 (2)−0.0069 (19)
C90.127 (4)0.085 (3)0.077 (3)−0.058 (3)−0.002 (3)−0.004 (2)
C100.201 (7)0.095 (4)0.080 (4)−0.084 (5)0.002 (4)0.003 (3)
C110.237 (10)0.088 (5)0.079 (4)−0.068 (6)−0.021 (5)−0.004 (3)
C120.155 (5)0.075 (3)0.062 (3)−0.007 (4)−0.026 (3)−0.014 (3)
C130.219 (9)0.090 (4)0.098 (5)0.057 (6)−0.038 (5)−0.027 (4)
C140.156 (7)0.199 (10)0.098 (5)0.087 (7)−0.025 (5)−0.034 (6)
C150.104 (4)0.209 (9)0.100 (5)0.037 (5)−0.001 (4)−0.018 (5)
C160.083 (3)0.121 (4)0.089 (3)0.009 (3)0.000 (3)−0.008 (3)
C170.101 (3)0.074 (3)0.057 (2)−0.007 (3)−0.009 (2)−0.013 (2)
C180.067 (2)0.062 (2)0.072 (2)−0.0216 (19)0.0000 (19)−0.0044 (19)
C190.089 (3)0.094 (3)0.106 (4)−0.024 (3)0.034 (3)−0.027 (3)
C200.070 (2)0.056 (2)0.0469 (19)−0.0196 (18)−0.0037 (17)−0.0068 (16)
C210.071 (3)0.071 (2)0.062 (2)−0.016 (2)−0.0101 (19)0.0071 (19)
C220.074 (3)0.124 (4)0.067 (3)−0.038 (3)−0.001 (2)−0.009 (3)
C230.117 (4)0.116 (4)0.050 (2)−0.069 (3)0.006 (3)−0.007 (3)
C240.137 (5)0.083 (3)0.056 (2)−0.051 (3)−0.002 (3)0.009 (2)
C250.087 (3)0.064 (2)0.056 (2)−0.019 (2)−0.013 (2)0.0050 (19)
C260.191 (7)0.221 (8)0.095 (4)−0.144 (7)0.015 (4)−0.004 (4)
C270.058 (2)0.0477 (18)0.0436 (17)−0.0085 (15)−0.0042 (15)−0.0026 (14)
C280.061 (2)0.057 (2)0.066 (2)−0.0184 (18)0.0022 (18)−0.0063 (17)
C290.069 (2)0.083 (3)0.078 (3)−0.029 (2)−0.001 (2)−0.004 (2)
C300.091 (3)0.077 (3)0.083 (3)−0.037 (3)−0.016 (3)−0.004 (2)
C310.098 (3)0.052 (2)0.069 (2)−0.015 (2)−0.017 (2)−0.0100 (19)
C320.070 (2)0.051 (2)0.0497 (19)−0.0059 (18)−0.0112 (17)−0.0006 (16)
C330.078 (3)0.056 (2)0.058 (2)0.005 (2)−0.005 (2)−0.0066 (18)
C340.062 (2)0.068 (3)0.071 (2)0.006 (2)0.0065 (19)−0.005 (2)
C350.050 (2)0.056 (2)0.065 (2)−0.0025 (17)−0.0003 (17)0.0030 (18)
C360.0481 (18)0.0480 (19)0.0523 (19)−0.0051 (15)−0.0015 (15)−0.0005 (15)
C370.0464 (18)0.0431 (18)0.064 (2)−0.0048 (14)−0.0061 (15)−0.0023 (15)
C380.0465 (17)0.0447 (18)0.060 (2)−0.0084 (14)−0.0026 (15)−0.0055 (15)
C390.055 (2)0.070 (3)0.073 (3)−0.0005 (18)0.0018 (19)−0.008 (2)
C400.076 (3)0.081 (3)0.068 (3)−0.009 (2)0.013 (2)−0.015 (2)
C410.089 (3)0.069 (3)0.061 (2)−0.027 (2)0.001 (2)−0.007 (2)
C420.075 (3)0.074 (3)0.066 (3)−0.011 (2)−0.010 (2)−0.001 (2)
C430.054 (2)0.067 (2)0.067 (2)−0.0070 (18)−0.0020 (18)−0.0086 (19)
C440.073 (2)0.048 (2)0.061 (2)−0.0082 (18)0.0039 (19)−0.0026 (17)
C450.084 (3)0.081 (3)0.101 (3)−0.008 (2)0.024 (3)0.018 (3)
C460.068 (2)0.0451 (19)0.0455 (18)−0.0144 (16)0.0030 (16)−0.0029 (15)
C470.088 (3)0.072 (3)0.061 (2)−0.016 (2)−0.010 (2)−0.013 (2)
C480.077 (3)0.105 (4)0.081 (3)−0.016 (3)−0.020 (2)0.003 (3)
C490.066 (3)0.081 (3)0.076 (3)−0.006 (2)0.014 (2)0.017 (2)
C500.080 (3)0.059 (2)0.067 (2)−0.005 (2)0.011 (2)−0.0061 (19)
C510.074 (2)0.062 (2)0.058 (2)−0.014 (2)−0.0058 (19)−0.0087 (18)
C520.072 (3)0.136 (5)0.144 (5)0.015 (3)0.022 (3)0.034 (4)
C530.0386 (16)0.0464 (18)0.069 (2)−0.0063 (14)−0.0032 (15)−0.0003 (16)
C540.053 (2)0.053 (2)0.063 (2)−0.0121 (16)0.0084 (16)−0.0035 (17)
C550.065 (2)0.059 (2)0.071 (2)−0.0135 (18)0.0023 (19)−0.0160 (19)
C560.063 (2)0.059 (3)0.103 (4)−0.0125 (19)−0.009 (2)−0.019 (2)
C570.063 (2)0.052 (2)0.113 (4)−0.0199 (19)−0.014 (2)0.001 (2)
C580.0474 (19)0.058 (2)0.085 (3)−0.0155 (17)−0.0019 (18)0.0094 (19)
C590.069 (3)0.076 (3)0.106 (4)−0.032 (2)−0.007 (2)0.028 (3)
C600.068 (3)0.102 (3)0.078 (3)−0.030 (2)0.001 (2)0.028 (3)
C610.053 (2)0.088 (3)0.057 (2)−0.0143 (19)0.0048 (17)0.005 (2)
C620.0451 (18)0.058 (2)0.060 (2)−0.0095 (15)0.0018 (15)0.0013 (17)
C630.065 (2)0.059 (2)0.055 (2)−0.0262 (18)0.0045 (17)−0.0107 (17)
C640.079 (3)0.052 (2)0.058 (2)−0.0221 (19)−0.0068 (19)−0.0111 (17)
C650.118 (4)0.061 (3)0.065 (3)−0.027 (3)−0.009 (2)−0.009 (2)
C660.150 (5)0.057 (3)0.079 (3)−0.029 (3)−0.038 (3)0.004 (2)
C670.109 (4)0.068 (3)0.122 (5)−0.013 (3)−0.046 (4)−0.005 (3)
C680.072 (3)0.080 (3)0.126 (4)−0.014 (3)−0.010 (3)−0.019 (3)
C690.070 (3)0.068 (3)0.085 (3)−0.014 (2)−0.006 (2)−0.003 (2)
C700.073 (3)0.062 (2)0.070 (2)−0.020 (2)−0.013 (2)−0.0050 (19)
C710.108 (4)0.127 (4)0.090 (3)−0.036 (3)−0.030 (3)−0.017 (3)
C720.060 (2)0.053 (2)0.077 (2)−0.0167 (18)−0.0134 (19)−0.0044 (18)
C730.062 (2)0.052 (2)0.103 (3)−0.0084 (18)−0.001 (2)−0.002 (2)
C740.068 (2)0.055 (2)0.100 (3)−0.016 (2)−0.006 (2)0.005 (2)
C750.061 (2)0.060 (2)0.082 (3)−0.0188 (19)−0.012 (2)−0.006 (2)
C760.051 (2)0.069 (3)0.087 (3)−0.0127 (19)−0.004 (2)−0.009 (2)
C770.062 (2)0.050 (2)0.096 (3)−0.0090 (18)−0.018 (2)−0.002 (2)
C780.081 (3)0.091 (3)0.108 (4)−0.029 (3)0.013 (3)−0.007 (3)
N20.0649 (19)0.071 (2)0.083 (2)−0.0212 (16)−0.0017 (16)−0.0115 (17)
N30.073 (2)0.0654 (19)0.0655 (19)−0.0184 (16)−0.0036 (15)−0.0163 (15)
N10.0672 (18)0.0509 (17)0.0645 (18)−0.0179 (14)−0.0019 (15)0.0030 (14)
O10.0465 (14)0.0728 (18)0.123 (3)−0.0096 (13)0.0032 (15)−0.0069 (17)
O30.098 (2)0.116 (3)0.0550 (16)−0.0339 (19)0.0088 (15)−0.0049 (17)
O20.105 (3)0.140 (3)0.128 (3)−0.075 (3)0.025 (2)−0.007 (3)

Geometric parameters (Å, °)

C1—C61.369 (5)C42—C431.382 (5)
C1—C21.374 (6)C42—H46A0.9300
C1—C71.525 (5)C43—H57A0.9300
C2—C31.389 (7)C44—N11.484 (5)
C2—H50A0.9300C44—C461.511 (5)
C3—C41.352 (7)C44—C451.523 (6)
C3—H75A0.9300C44—H32A0.9800
C4—C51.370 (7)C45—H56A0.9600
C4—H67A0.9300C45—H56B0.9600
C5—C61.384 (6)C45—H56C0.9600
C5—H61A0.9300C46—C471.371 (5)
C6—H53A0.9300C46—C511.387 (5)
C7—N21.492 (5)C47—C481.380 (6)
C7—C81.520 (6)C47—H64A0.9300
C7—H30A0.9800C48—C491.382 (7)
C8—C91.381 (6)C48—H71A0.9300
C8—C171.416 (6)C49—C501.363 (6)
C9—O21.359 (6)C49—C521.513 (6)
C9—C101.417 (8)C50—C511.370 (5)
C10—C111.320 (9)C50—H59A0.9300
C10—H73A0.9300C51—H22A0.9300
C11—C121.381 (9)C52—H82A0.9600
C11—H76A0.9300C52—H82B0.9600
C12—C131.371 (10)C52—H82C0.9600
C12—C171.464 (7)C53—C541.409 (5)
C13—C141.374 (13)C53—C581.415 (5)
C13—H81A0.9300C53—C621.426 (5)
C14—C151.394 (13)C54—C551.369 (5)
C14—H83A0.9300C54—H4A0.9300
C15—C161.385 (8)C55—C561.383 (6)
C15—H84A0.9300C55—H15A0.9300
C16—C171.385 (7)C56—C571.337 (6)
C16—H72A0.9300C56—H41A0.9300
C18—N21.490 (5)C57—C581.416 (6)
C18—C201.513 (5)C57—H21A0.9300
C18—C191.533 (6)C58—C591.408 (6)
C18—H99A0.9800C59—C601.342 (7)
C19—H79A0.9600C59—H26A0.9300
C19—H79B0.9600C60—C611.412 (6)
C19—H79C0.9600C60—H43A0.9300
C20—C211.372 (5)C61—O31.353 (5)
C20—C251.387 (5)C61—C621.380 (5)
C21—C221.382 (6)C62—C631.523 (5)
C21—H54A0.9300C63—N31.488 (4)
C22—C231.350 (7)C63—C641.525 (5)
C22—H51A0.9300C63—H25A0.9800
C23—C241.374 (7)C64—C691.383 (6)
C23—C261.519 (7)C64—C651.387 (6)
C24—C251.376 (6)C65—C661.399 (7)
C24—H52A0.9300C65—H55A0.9300
C25—H27A0.9300C66—C671.342 (8)
C26—H10D0.9600C66—H70A0.9300
C26—H10E0.9600C67—C681.355 (8)
C26—H10F0.9600C67—H74A0.9300
C27—C281.405 (5)C68—C691.385 (6)
C27—C321.419 (5)C68—H68A0.9300
C27—C361.428 (5)C69—H63A0.9300
C28—C291.382 (5)C70—N31.477 (5)
C28—H3A0.9300C70—C721.514 (6)
C29—C301.395 (6)C70—C711.516 (6)
C29—H47A0.9300C70—H37A0.9800
C30—C311.353 (6)C71—H77A0.9600
C30—H44A0.9300C71—H77B0.9600
C31—C321.427 (6)C71—H77C0.9600
C31—H20A0.9300C72—C731.382 (5)
C32—C331.408 (6)C72—C771.392 (5)
C33—C341.328 (6)C73—C741.371 (6)
C33—H18A0.9300C73—H49A0.9300
C34—C351.418 (6)C74—C751.388 (5)
C34—H35A0.9300C74—H48A0.9300
C35—O11.350 (5)C75—C761.368 (6)
C35—C361.391 (5)C75—C781.503 (6)
C36—C371.523 (5)C76—C771.373 (6)
C37—N11.476 (4)C76—H19A0.9300
C37—C381.520 (5)C77—H42A0.9300
C37—H6A0.9800C78—H10A0.9600
C38—C391.373 (5)C78—H10B0.9600
C38—C431.379 (5)C78—H10C0.9600
C39—C401.368 (6)N2—H1A0.9000
C39—H36A0.9300N3—H3C0.9000
C40—C411.366 (6)N1—H4B0.9001
C40—H80A0.9300O1—H10.8200
C41—C421.363 (6)O3—H20.8200
C41—H38A0.9300O2—H80.8200
C6—C1—C2117.9 (4)C38—C43—C42120.5 (3)
C6—C1—C7123.0 (4)C38—C43—H57A119.8
C2—C1—C7119.1 (3)C42—C43—H57A119.8
C1—C2—C3120.7 (4)N1—C44—C46114.4 (3)
C1—C2—H50A119.7N1—C44—C45107.8 (3)
C3—C2—H50A119.7C46—C44—C45111.4 (3)
C4—C3—C2120.5 (5)N1—C44—H32A107.7
C4—C3—H75A119.7C46—C44—H32A107.7
C2—C3—H75A119.7C45—C44—H32A107.7
C3—C4—C5119.8 (5)C44—C45—H56A109.5
C3—C4—H67A120.1C44—C45—H56B109.5
C5—C4—H67A120.1H56A—C45—H56B109.5
C4—C5—C6119.5 (4)C44—C45—H56C109.5
C4—C5—H61A120.3H56A—C45—H56C109.5
C6—C5—H61A120.3H56B—C45—H56C109.5
C1—C6—C5121.7 (4)C47—C46—C51116.8 (3)
C1—C6—H53A119.2C47—C46—C44121.2 (3)
C5—C6—H53A119.2C51—C46—C44122.0 (3)
N2—C7—C8110.6 (3)C46—C47—C48122.1 (4)
N2—C7—C1109.7 (3)C46—C47—H64A118.9
C8—C7—C1113.1 (3)C48—C47—H64A118.9
N2—C7—H30A107.8C47—C48—C49120.7 (4)
C8—C7—H30A107.8C47—C48—H71A119.7
C1—C7—H30A107.8C49—C48—H71A119.7
C9—C8—C17118.6 (4)C50—C49—C48117.0 (4)
C9—C8—C7120.5 (4)C50—C49—C52122.4 (5)
C17—C8—C7120.8 (4)C48—C49—C52120.5 (5)
O2—C9—C8123.6 (4)C49—C50—C51122.7 (4)
O2—C9—C10115.4 (6)C49—C50—H59A118.7
C8—C9—C10121.0 (6)C51—C50—H59A118.7
C11—C10—C9120.2 (7)C50—C51—C46120.7 (4)
C11—C10—H73A119.9C50—C51—H22A119.7
C9—C10—H73A119.9C46—C51—H22A119.7
C10—C11—C12123.3 (6)C49—C52—H82A109.5
C10—C11—H76A118.3C49—C52—H82B109.5
C12—C11—H76A118.3H82A—C52—H82B109.5
C13—C12—C11123.2 (8)C49—C52—H82C109.5
C13—C12—C17119.2 (7)H82A—C52—H82C109.5
C11—C12—C17117.5 (6)H82B—C52—H82C109.5
C12—C13—C14122.1 (8)C54—C53—C58116.5 (3)
C12—C13—H81A118.9C54—C53—C62122.9 (3)
C14—C13—H81A118.9C58—C53—C62120.6 (3)
C13—C14—C15119.3 (7)C55—C54—C53122.1 (4)
C13—C14—H83A120.3C55—C54—H4A119.0
C15—C14—H83A120.3C53—C54—H4A119.0
C16—C15—C14120.3 (8)C54—C55—C56120.3 (4)
C16—C15—H84A119.8C54—C55—H15A119.8
C14—C15—H84A119.8C56—C55—H15A119.8
C15—C16—C17121.8 (7)C57—C56—C55119.9 (4)
C15—C16—H72A119.1C57—C56—H41A120.0
C17—C16—H72A119.1C55—C56—H41A120.0
C16—C17—C8123.6 (4)C56—C57—C58121.7 (4)
C16—C17—C12117.2 (5)C56—C57—H21A119.2
C8—C17—C12119.2 (5)C58—C57—H21A119.2
N2—C18—C20113.1 (3)C59—C58—C53117.9 (4)
N2—C18—C19107.9 (3)C59—C58—C57122.6 (4)
C20—C18—C19112.7 (3)C53—C58—C57119.5 (4)
N2—C18—H99A107.6C60—C59—C58121.7 (4)
C20—C18—H99A107.6C60—C59—H26A119.1
C19—C18—H99A107.6C58—C59—H26A119.1
C18—C19—H79A109.5C59—C60—C61120.7 (4)
C18—C19—H79B109.5C59—C60—H43A119.7
H79A—C19—H79B109.5C61—C60—H43A119.7
C18—C19—H79C109.5O3—C61—C62124.0 (4)
H79A—C19—H79C109.5O3—C61—C60115.4 (4)
H79B—C19—H79C109.5C62—C61—C60120.6 (4)
C21—C20—C25116.9 (4)C61—C62—C53118.4 (3)
C21—C20—C18120.8 (3)C61—C62—C63121.9 (3)
C25—C20—C18122.2 (3)C53—C62—C63119.6 (3)
C20—C21—C22120.6 (4)N3—C63—C62111.4 (3)
C20—C21—H54A119.7N3—C63—C64108.8 (3)
C22—C21—H54A119.7C62—C63—C64112.7 (3)
C23—C22—C21122.4 (5)N3—C63—H25A107.9
C23—C22—H51A118.8C62—C63—H25A107.9
C21—C22—H51A118.8C64—C63—H25A107.9
C22—C23—C24117.7 (4)C69—C64—C65118.4 (4)
C22—C23—C26122.8 (6)C69—C64—C63121.4 (3)
C24—C23—C26119.5 (5)C65—C64—C63120.2 (4)
C23—C24—C25120.7 (4)C64—C65—C66119.6 (5)
C23—C24—H52A119.6C64—C65—H55A120.2
C25—C24—H52A119.6C66—C65—H55A120.2
C24—C25—C20121.6 (4)C67—C66—C65120.9 (5)
C24—C25—H27A119.2C67—C66—H70A119.6
C20—C25—H27A119.2C65—C66—H70A119.6
C23—C26—H10D109.5C66—C67—C68120.2 (5)
C23—C26—H10E109.5C66—C67—H74A119.9
H10D—C26—H10E109.5C68—C67—H74A119.9
C23—C26—H10F109.5C67—C68—C69120.6 (5)
H10D—C26—H10F109.5C67—C68—H68A119.7
H10E—C26—H10F109.5C69—C68—H68A119.7
C28—C27—C32117.1 (3)C64—C69—C68120.3 (4)
C28—C27—C36123.0 (3)C64—C69—H63A119.8
C32—C27—C36119.9 (3)C68—C69—H63A119.8
C29—C28—C27122.5 (4)N3—C70—C72115.3 (3)
C29—C28—H3A118.8N3—C70—C71107.3 (4)
C27—C28—H3A118.8C72—C70—C71111.9 (4)
C28—C29—C30119.6 (4)N3—C70—H37A107.4
C28—C29—H47A120.2C72—C70—H37A107.4
C30—C29—H47A120.2C71—C70—H37A107.4
C31—C30—C29120.1 (4)C70—C71—H77A109.5
C31—C30—H44A119.9C70—C71—H77B109.5
C29—C30—H44A119.9H77A—C71—H77B109.5
C30—C31—C32121.3 (4)C70—C71—H77C109.5
C30—C31—H20A119.3H77A—C71—H77C109.5
C32—C31—H20A119.3H77B—C71—H77C109.5
C33—C32—C27119.1 (4)C73—C72—C77116.7 (4)
C33—C32—C31121.6 (4)C73—C72—C70122.2 (4)
C27—C32—C31119.3 (3)C77—C72—C70121.0 (3)
C34—C33—C32121.1 (4)C74—C73—C72122.4 (4)
C34—C33—H18A119.5C74—C73—H49A118.8
C32—C33—H18A119.5C72—C73—H49A118.8
C33—C34—C35121.4 (4)C73—C74—C75120.5 (4)
C33—C34—H35A119.3C73—C74—H48A119.8
C35—C34—H35A119.3C75—C74—H48A119.8
O1—C35—C36122.7 (3)C76—C75—C74117.4 (4)
O1—C35—C34116.9 (3)C76—C75—C78122.2 (4)
C36—C35—C34120.4 (4)C74—C75—C78120.4 (4)
C35—C36—C27118.2 (3)C75—C76—C77122.4 (4)
C35—C36—C37121.6 (3)C75—C76—H19A118.8
C27—C36—C37120.3 (3)C77—C76—H19A118.8
N1—C37—C38109.6 (3)C76—C77—C72120.7 (4)
N1—C37—C36110.7 (3)C76—C77—H42A119.7
C38—C37—C36113.8 (3)C72—C77—H42A119.7
N1—C37—H6A107.5C75—C78—H10A109.5
C38—C37—H6A107.5C75—C78—H10B109.5
C36—C37—H6A107.5H10A—C78—H10B109.5
C39—C38—C43118.0 (3)C75—C78—H10C109.5
C39—C38—C37121.1 (3)H10A—C78—H10C109.5
C43—C38—C37120.9 (3)H10B—C78—H10C109.5
C40—C39—C38121.6 (4)C18—N2—C7112.9 (3)
C40—C39—H36A119.2C18—N2—H1A108.6
C38—C39—H36A119.2C7—N2—H1A108.5
C41—C40—C39120.0 (4)C70—N3—C63115.2 (3)
C41—C40—H80A120.0C70—N3—H3C107.9
C39—C40—H80A120.0C63—N3—H3C108.0
C42—C41—C40119.7 (4)C37—N1—C44114.0 (3)
C42—C41—H38A120.2C37—N1—H4B108.4
C40—C41—H38A120.2C44—N1—H4B108.4
C41—C42—C43120.3 (4)C35—O1—H1109.5
C41—C42—H46A119.8C61—O3—H2109.5
C43—C42—H46A119.8C9—O2—H8109.5
C6—C1—C2—C30.1 (6)C37—C38—C39—C40178.3 (4)
C7—C1—C2—C3179.3 (4)C38—C39—C40—C41−1.0 (7)
C1—C2—C3—C4−1.1 (7)C39—C40—C41—C42−0.1 (6)
C2—C3—C4—C52.3 (7)C40—C41—C42—C430.8 (6)
C3—C4—C5—C6−2.4 (7)C39—C38—C43—C42−0.6 (5)
C2—C1—C6—C5−0.2 (6)C37—C38—C43—C42−177.5 (3)
C7—C1—C6—C5−179.4 (4)C41—C42—C43—C38−0.4 (6)
C4—C5—C6—C11.4 (6)N1—C44—C46—C47129.5 (4)
C6—C1—C7—N267.8 (4)C45—C44—C46—C47−107.9 (4)
C2—C1—C7—N2−111.4 (4)N1—C44—C46—C51−53.4 (5)
C6—C1—C7—C8−56.2 (5)C45—C44—C46—C5169.2 (5)
C2—C1—C7—C8124.6 (4)C51—C46—C47—C48−0.6 (6)
N2—C7—C8—C9−38.1 (5)C44—C46—C47—C48176.7 (4)
C1—C7—C8—C985.4 (5)C46—C47—C48—C490.6 (7)
N2—C7—C8—C17145.2 (4)C47—C48—C49—C50−1.2 (6)
C1—C7—C8—C17−91.3 (4)C47—C48—C49—C52−180.0 (5)
C17—C8—C9—O2−176.4 (4)C48—C49—C50—C512.0 (6)
C7—C8—C9—O26.8 (6)C52—C49—C50—C51−179.3 (4)
C17—C8—C9—C103.3 (6)C49—C50—C51—C46−2.1 (6)
C7—C8—C9—C10−173.4 (4)C47—C46—C51—C501.3 (6)
O2—C9—C10—C11177.7 (5)C44—C46—C51—C50−176.0 (3)
C8—C9—C10—C11−2.1 (8)C58—C53—C54—C550.9 (5)
C9—C10—C11—C12−0.6 (10)C62—C53—C54—C55−178.5 (3)
C10—C11—C12—C13−178.7 (6)C53—C54—C55—C56−0.7 (5)
C10—C11—C12—C171.9 (8)C54—C55—C56—C57−0.2 (6)
C11—C12—C13—C14−179.5 (7)C55—C56—C57—C580.9 (6)
C17—C12—C13—C14−0.2 (10)C54—C53—C58—C59178.1 (3)
C12—C13—C14—C15−0.4 (12)C62—C53—C58—C59−2.5 (5)
C13—C14—C15—C160.8 (12)C54—C53—C58—C57−0.2 (5)
C14—C15—C16—C17−0.6 (10)C62—C53—C58—C57179.2 (3)
C15—C16—C17—C8−179.7 (5)C56—C57—C58—C59−178.9 (4)
C15—C16—C17—C120.0 (8)C56—C57—C58—C53−0.7 (6)
C9—C8—C17—C16177.7 (4)C53—C58—C59—C600.9 (6)
C7—C8—C17—C16−5.6 (6)C57—C58—C59—C60179.2 (4)
C9—C8—C17—C12−2.0 (6)C58—C59—C60—C611.1 (6)
C7—C8—C17—C12174.7 (4)C59—C60—C61—O3178.3 (4)
C13—C12—C17—C160.4 (7)C59—C60—C61—C62−1.7 (6)
C11—C12—C17—C16179.8 (5)O3—C61—C62—C53−179.8 (3)
C13—C12—C17—C8−179.9 (5)C60—C61—C62—C530.1 (5)
C11—C12—C17—C8−0.5 (6)O3—C61—C62—C633.8 (5)
N2—C18—C20—C21110.8 (4)C60—C61—C62—C63−176.2 (3)
C19—C18—C20—C21−126.5 (4)C54—C53—C62—C61−178.7 (3)
N2—C18—C20—C25−67.5 (4)C58—C53—C62—C612.0 (5)
C19—C18—C20—C2555.2 (5)C54—C53—C62—C63−2.3 (5)
C25—C20—C21—C22−0.6 (6)C58—C53—C62—C63178.4 (3)
C18—C20—C21—C22−179.1 (4)C61—C62—C63—N3−27.7 (4)
C20—C21—C22—C230.8 (7)C53—C62—C63—N3156.1 (3)
C21—C22—C23—C24−0.3 (7)C61—C62—C63—C6495.0 (4)
C21—C22—C23—C26179.0 (5)C53—C62—C63—C64−81.3 (4)
C22—C23—C24—C25−0.3 (7)N3—C63—C64—C6975.9 (4)
C26—C23—C24—C25−179.6 (4)C62—C63—C64—C69−48.2 (4)
C23—C24—C25—C200.4 (6)N3—C63—C64—C65−101.5 (4)
C21—C20—C25—C240.1 (6)C62—C63—C64—C65134.4 (4)
C18—C20—C25—C24178.5 (4)C69—C64—C65—C660.7 (5)
C32—C27—C28—C292.1 (5)C63—C64—C65—C66178.1 (3)
C36—C27—C28—C29−178.3 (3)C64—C65—C66—C67−2.2 (6)
C27—C28—C29—C30−0.2 (6)C65—C66—C67—C682.3 (7)
C28—C29—C30—C31−1.1 (6)C66—C67—C68—C69−1.0 (8)
C29—C30—C31—C320.4 (6)C65—C64—C69—C680.6 (6)
C28—C27—C32—C33179.9 (3)C63—C64—C69—C68−176.8 (4)
C36—C27—C32—C330.4 (5)C67—C68—C69—C64−0.5 (7)
C28—C27—C32—C31−2.8 (5)N3—C70—C72—C73−39.3 (5)
C36—C27—C32—C31177.7 (3)C71—C70—C72—C7383.6 (5)
C30—C31—C32—C33178.8 (4)N3—C70—C72—C77144.6 (3)
C30—C31—C32—C271.6 (6)C71—C70—C72—C77−92.5 (5)
C27—C32—C33—C34−2.1 (5)C77—C72—C73—C74−0.6 (6)
C31—C32—C33—C34−179.3 (4)C70—C72—C73—C74−176.9 (4)
C32—C33—C34—C351.6 (6)C72—C73—C74—C751.7 (6)
C33—C34—C35—O1−178.6 (4)C73—C74—C75—C76−1.7 (6)
C33—C34—C35—C360.6 (6)C73—C74—C75—C78179.4 (4)
O1—C35—C36—C27177.0 (3)C74—C75—C76—C770.6 (6)
C34—C35—C36—C27−2.3 (5)C78—C75—C76—C77179.5 (4)
O1—C35—C36—C37−3.0 (5)C75—C76—C77—C720.5 (6)
C34—C35—C36—C37177.8 (3)C73—C72—C77—C76−0.5 (5)
C28—C27—C36—C35−177.8 (3)C70—C72—C77—C76175.8 (3)
C32—C27—C36—C351.8 (5)C20—C18—N2—C7−59.9 (4)
C28—C27—C36—C372.2 (5)C19—C18—N2—C7174.8 (3)
C32—C27—C36—C37−178.3 (3)C8—C7—N2—C18−74.3 (4)
C35—C36—C37—N1−26.7 (4)C1—C7—N2—C18160.3 (3)
C27—C36—C37—N1153.4 (3)C72—C70—N3—C63−55.4 (4)
C35—C36—C37—C3897.3 (4)C71—C70—N3—C63179.3 (4)
C27—C36—C37—C38−82.6 (4)C62—C63—N3—C70−84.7 (4)
N1—C37—C38—C39−104.1 (4)C64—C63—N3—C70150.5 (3)
C36—C37—C38—C39131.2 (4)C38—C37—N1—C44156.8 (3)
N1—C37—C38—C4372.7 (4)C36—C37—N1—C44−76.8 (3)
C36—C37—C38—C43−51.9 (4)C46—C44—N1—C37−68.9 (4)
C43—C38—C39—C401.3 (6)C45—C44—N1—C37166.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.571 (4)144.
O2—H8···N20.821.922.629 (5)144.
O3—H2···N30.821.872.597 (5)147.
C6—H53A···O20.932.583.327 (6)138.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2220).

References

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