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Acta Cryst. (2009). E65, o509    [ doi:10.1107/S1600536808043924 ]

Bis{6-[4-(2-ethyoxyphenyldiazenyl)phenoxy]hexanol} monohydrate

R. Lu, M. Zhang, L. Han, B. Wang and H. Wang

Abstract top

The asymmetric unit of the title compound, 2C20H26N2O3·H2O, contains two independent molecules and one water molecule. The azo bonds adopt trans conformations and the dihedral angles between the aromatic rings in the two organic molecules are 4.5 (2) and 1.5 (2)°. In the crystal structure, O-H...O and C-H...O hydrogen bonds help to establish the packing.

Comment top

The photophysical properties of azo compounds are of interest in the development of nonlinear optical and optical data storage materials (e.g. Bach et al., 1996). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The title compound, C20H26N2O3, contains two independent molecules and one water molecule, which form intermolecular O—H..O and C—H···O hydrogen bonds (Table 1).

Related literature top

For the synthesis, see: Zhao et al. (2002). For background, see: Bach et al. (1996).

Experimental top

The title compound was prepared by the literature method (Zhao et al., 2002). Yellow blocks of (I) were obtained by slow evaporation of an ethanol solution.

Refinement top

The H were placed geometrically with C—H = 0.93–0.97 Å and O—H = 0.85Å and refined as riding with Uiso(H) = 1.2Ueq(C,O) or 1.5Ueq(methyl C).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level. Dashed lines indicate hydrogen bonds.
Bis{6-[4-(2-ethyoxyphenyldiazenyl)phenoxy]hexanol} monohydrate top
Crystal data top
2C20H26N2O3·H2OZ = 2
Mr = 702.87F(000) = 756
Triclinic, P1Dx = 1.184 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4586 (7) ÅCell parameters from 25 reflections
b = 11.5674 (11) Åθ = 9–13°
c = 24.070 (2) ŵ = 0.08 mm−1
α = 90.46 (3)°T = 293 K
β = 98.46 (3)°Block, yellow
γ = 106.10 (3)°0.30 × 0.20 × 0.10 mm
V = 1970.9 (5) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer		3403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
graphiteθmax = 25.3°, θmin = 1.7°
ω/2θ scansh = 0→8
Absorption correction: ψ scan
(North et al., 1968)		k = −13→13
Tmin = 0.956, Tmax = 0.982l = −28→28
7726 measured reflections3 standard reflections every 200 reflections
7134 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.05P)2 + 1.3P]
where P = (Fo2 + 2Fc2)/3
7134 reflections(Δ/σ)max < 0.001
460 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
2C20H26N2O3·H2Oγ = 106.10 (3)°
Mr = 702.87V = 1970.9 (5) Å3
Triclinic, P1Z = 2
a = 7.4586 (7) ÅMo Kα radiation
b = 11.5674 (11) ŵ = 0.08 mm−1
c = 24.070 (2) ÅT = 293 K
α = 90.46 (3)°0.30 × 0.20 × 0.10 mm
β = 98.46 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		3403 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.077
Tmin = 0.956, Tmax = 0.982θmax = 25.3°
7726 measured reflections3 standard reflections every 200 reflections
7134 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.181Δρmax = 0.21 e Å−3
S = 1.00Δρmin = −0.30 e Å−3
7134 reflectionsAbsolute structure: ?
460 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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*/Ueq
OW0.5276 (4)0.9282 (2)−0.24533 (12)0.0971 (10)
HWB0.45220.8576−0.25050.117*
HWA0.46670.9734−0.23390.117*
O1−0.2094 (4)0.8215 (3)0.72415 (13)0.1066 (11)
H1A−0.23900.88730.72490.128*
O2−0.2623 (4)0.2599 (2)0.47771 (11)0.0815 (8)
O3−0.2369 (4)−0.2649 (2)0.26105 (10)0.0694 (7)
N1−0.2457 (5)−0.2022 (3)0.41759 (13)0.0670 (9)
N2−0.2520 (4)−0.2221 (2)0.36679 (13)0.0592 (8)
C1−0.2298 (6)0.7803 (4)0.66703 (19)0.0878 (14)
H1C−0.12980.83200.64950.105*
H1D−0.34950.78640.64720.105*
C2−0.2224 (6)0.6527 (3)0.66147 (16)0.0724 (11)
H2B−0.32420.60140.67840.087*
H2C−0.10430.64670.68250.087*
C3−0.2381 (6)0.6057 (3)0.60160 (16)0.0725 (11)
H3A−0.13020.65230.58560.087*
H3B−0.35090.61760.57960.087*
C4−0.2468 (5)0.4737 (3)0.59679 (15)0.0639 (10)
H4A−0.35720.42710.61170.077*
H4B−0.13630.46150.62000.077*
C5−0.2556 (6)0.4259 (3)0.53730 (15)0.0674 (10)
H5A−0.37030.43270.51440.081*
H5B−0.14900.47470.52140.081*
C6−0.2523 (6)0.2965 (3)0.53547 (15)0.0682 (11)
H6A−0.13690.28860.55750.082*
H6B−0.35890.24640.55090.082*
C7−0.2574 (5)0.1447 (3)0.46608 (16)0.0641 (10)
C8−0.2501 (6)0.0598 (3)0.50434 (16)0.0780 (12)
H8A−0.24760.07790.54220.094*
C9−0.2466 (6)−0.0536 (4)0.48678 (16)0.0810 (13)
H9A−0.2415−0.11140.51310.097*
C10−0.2504 (5)−0.0821 (3)0.43104 (15)0.0578 (9)
C11−0.2537 (6)0.0043 (3)0.39299 (16)0.0712 (11)
H11A−0.2522−0.01290.35530.085*
C12−0.2592 (6)0.1153 (4)0.40993 (16)0.0804 (13)
H12A−0.26430.17280.38340.096*
C13−0.2518 (5)−0.3409 (3)0.35068 (15)0.0527 (9)
C14−0.2609 (5)−0.4337 (3)0.38626 (16)0.0648 (10)
H14A−0.2637−0.41990.42420.078*
C15−0.2659 (5)−0.5478 (3)0.36662 (18)0.0702 (11)
H15A−0.2720−0.61020.39100.084*
C16−0.2618 (5)−0.5669 (4)0.31014 (19)0.0725 (11)
H16A−0.2657−0.64310.29650.087*
C17−0.2520 (5)−0.4757 (3)0.27399 (17)0.0656 (10)
H17A−0.2481−0.49010.23620.079*
C18−0.2479 (5)−0.3613 (3)0.29358 (15)0.0556 (9)
C19−0.2130 (6)−0.2753 (3)0.20418 (15)0.0675 (11)
H19A−0.3237−0.33170.18290.081*
H19B−0.1040−0.30420.20160.081*
C20−0.1848 (6)−0.1522 (4)0.18134 (17)0.0864 (13)
H20A−0.1668−0.15570.14280.130*
H20B−0.0755−0.09720.20290.130*
H20C−0.2940−0.12500.18380.130*
O40.1625 (4)0.8614 (2)−0.22791 (12)0.0906 (9)
H4C0.07040.8070−0.24580.109*
O50.2453 (4)0.3308 (2)0.01659 (10)0.0768 (8)
O60.2785 (4)−0.1956 (2)0.24180 (10)0.0668 (7)
N30.2699 (5)−0.1229 (3)0.08391 (13)0.0689 (9)
N40.2798 (4)−0.1396 (2)0.13469 (12)0.0581 (8)
C210.1799 (6)0.8282 (4)−0.17127 (19)0.0852 (13)
H21A0.06670.8301−0.15640.102*
H21B0.28570.8874−0.14940.102*
C220.2088 (6)0.7064 (3)−0.16406 (16)0.0707 (11)
H22A0.32610.7065−0.17690.085*
H22B0.10730.6484−0.18810.085*
C230.2158 (6)0.6645 (3)−0.10461 (16)0.0661 (10)
H23A0.32280.7186−0.08080.079*
H23B0.10200.6683−0.09060.079*
C240.2325 (6)0.5374 (3)−0.10095 (15)0.0658 (10)
H24A0.12790.4842−0.12600.079*
H24B0.34840.5346−0.11390.079*
C250.2330 (6)0.4913 (3)−0.04241 (15)0.0664 (10)
H25A0.34310.5407−0.01790.080*
H25B0.12170.4995−0.02820.080*
C260.2352 (6)0.3623 (3)−0.04032 (15)0.0671 (10)
H26A0.12150.3109−0.06260.081*
H26B0.34350.3519−0.05550.081*
C270.2510 (5)0.2175 (3)0.03082 (15)0.0614 (10)
C280.2504 (6)0.1940 (3)0.08671 (16)0.0737 (12)
H28A0.24520.25390.11190.088*
C290.2573 (6)0.0849 (3)0.10573 (15)0.0677 (11)
H29A0.25660.07070.14370.081*
C300.2656 (5)−0.0058 (3)0.06852 (15)0.0616 (10)
C310.2649 (7)0.0181 (4)0.01333 (16)0.0855 (14)
H31A0.2687−0.0422−0.01190.103*
C320.2589 (7)0.1291 (4)−0.00667 (17)0.0846 (13)
H32A0.26010.1436−0.04460.102*
C330.2824 (5)−0.2583 (3)0.14889 (15)0.0536 (9)
C340.2858 (5)−0.3467 (3)0.11001 (16)0.0619 (10)
H34A0.2862−0.32920.07240.074*
C350.2887 (5)−0.4604 (3)0.12658 (19)0.0705 (11)
H35A0.2898−0.51910.10010.085*
C360.2898 (5)−0.4861 (3)0.1814 (2)0.0741 (11)
H36A0.2926−0.56270.19220.089*
C370.2870 (5)−0.4001 (3)0.22214 (17)0.0679 (11)
H37A0.2871−0.41870.25970.081*
C380.2839 (5)−0.2860 (3)0.20512 (16)0.0580 (9)
C390.2613 (6)−0.2236 (4)0.29842 (15)0.0755 (12)
H39A0.3771−0.23740.31730.091*
H39B0.1586−0.29600.29960.091*
C400.2227 (7)−0.1189 (4)0.32730 (17)0.0897 (14)
H40A0.2108−0.13610.36580.135*
H40B0.1075−0.10620.30850.135*
H40C0.3252−0.04770.32610.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
OW0.102 (2)0.0739 (19)0.120 (2)0.0148 (17)0.0522 (19)−0.0047 (17)
O10.111 (3)0.095 (2)0.123 (3)0.0508 (19)0.008 (2)−0.050 (2)
O20.128 (3)0.0624 (17)0.0648 (18)0.0391 (17)0.0244 (16)−0.0029 (13)
O30.097 (2)0.0609 (16)0.0555 (16)0.0248 (15)0.0232 (14)−0.0032 (13)
N10.089 (2)0.062 (2)0.055 (2)0.0276 (18)0.0165 (17)−0.0053 (15)
N20.066 (2)0.0560 (19)0.059 (2)0.0185 (15)0.0193 (16)−0.0019 (15)
C10.091 (3)0.073 (3)0.102 (4)0.031 (3)0.010 (3)−0.029 (3)
C20.065 (3)0.073 (3)0.081 (3)0.026 (2)0.006 (2)−0.019 (2)
C30.083 (3)0.057 (2)0.081 (3)0.021 (2)0.025 (2)−0.011 (2)
C40.065 (3)0.060 (2)0.072 (3)0.0217 (19)0.018 (2)−0.0085 (19)
C50.083 (3)0.061 (2)0.065 (2)0.029 (2)0.015 (2)−0.0009 (19)
C60.087 (3)0.066 (3)0.055 (2)0.024 (2)0.015 (2)−0.0097 (19)
C70.078 (3)0.052 (2)0.067 (3)0.022 (2)0.020 (2)−0.008 (2)
C80.125 (4)0.066 (3)0.052 (2)0.040 (3)0.017 (2)−0.002 (2)
C90.130 (4)0.068 (3)0.053 (2)0.038 (3)0.021 (2)0.004 (2)
C100.063 (2)0.050 (2)0.063 (2)0.0184 (18)0.0158 (19)−0.0029 (18)
C110.101 (3)0.063 (3)0.055 (2)0.026 (2)0.024 (2)−0.004 (2)
C120.129 (4)0.064 (3)0.057 (3)0.036 (3)0.027 (2)0.002 (2)
C130.048 (2)0.050 (2)0.063 (2)0.0176 (17)0.0127 (17)−0.0029 (18)
C140.071 (3)0.058 (2)0.071 (3)0.022 (2)0.020 (2)0.003 (2)
C150.071 (3)0.057 (2)0.086 (3)0.022 (2)0.017 (2)0.011 (2)
C160.073 (3)0.057 (3)0.091 (3)0.023 (2)0.015 (2)−0.005 (2)
C170.072 (3)0.057 (2)0.070 (3)0.021 (2)0.013 (2)−0.010 (2)
C180.057 (2)0.052 (2)0.058 (2)0.0153 (18)0.0094 (18)0.0027 (18)
C190.066 (3)0.075 (3)0.061 (2)0.016 (2)0.018 (2)−0.006 (2)
C200.100 (4)0.084 (3)0.073 (3)0.015 (3)0.026 (3)0.009 (2)
O40.089 (2)0.082 (2)0.091 (2)0.0152 (17)−0.0022 (17)0.0206 (17)
O50.114 (2)0.0645 (17)0.0610 (17)0.0322 (16)0.0270 (15)0.0108 (13)
O60.0854 (19)0.0619 (16)0.0582 (16)0.0240 (14)0.0210 (13)0.0053 (13)
N30.100 (3)0.060 (2)0.053 (2)0.0308 (18)0.0152 (18)0.0057 (15)
N40.065 (2)0.0559 (19)0.057 (2)0.0197 (16)0.0174 (15)0.0067 (15)
C210.090 (3)0.078 (3)0.099 (4)0.032 (3)0.037 (3)0.024 (3)
C220.081 (3)0.062 (2)0.070 (3)0.019 (2)0.019 (2)0.012 (2)
C230.071 (3)0.059 (2)0.075 (3)0.023 (2)0.020 (2)0.0070 (19)
C240.075 (3)0.063 (2)0.069 (3)0.027 (2)0.024 (2)0.0096 (19)
C250.075 (3)0.064 (2)0.068 (3)0.029 (2)0.017 (2)0.0091 (19)
C260.076 (3)0.069 (3)0.060 (2)0.023 (2)0.019 (2)0.009 (2)
C270.074 (3)0.055 (2)0.059 (2)0.023 (2)0.013 (2)0.0095 (19)
C280.115 (4)0.057 (2)0.060 (3)0.032 (2)0.031 (2)0.007 (2)
C290.093 (3)0.070 (3)0.047 (2)0.028 (2)0.024 (2)0.0092 (19)
C300.074 (3)0.057 (2)0.059 (2)0.023 (2)0.018 (2)0.0036 (18)
C310.151 (4)0.069 (3)0.051 (2)0.052 (3)0.021 (3)0.001 (2)
C320.139 (4)0.072 (3)0.055 (2)0.043 (3)0.029 (3)0.005 (2)
C330.054 (2)0.047 (2)0.063 (2)0.0159 (17)0.0123 (18)0.0005 (17)
C340.062 (3)0.062 (2)0.067 (2)0.023 (2)0.0120 (19)−0.0024 (19)
C350.066 (3)0.058 (3)0.091 (3)0.024 (2)0.011 (2)−0.009 (2)
C360.068 (3)0.051 (2)0.104 (3)0.018 (2)0.014 (2)0.008 (2)
C370.065 (3)0.060 (3)0.080 (3)0.020 (2)0.012 (2)0.011 (2)
C380.053 (2)0.053 (2)0.070 (3)0.0146 (18)0.0137 (19)−0.0017 (19)
C390.084 (3)0.086 (3)0.056 (3)0.022 (2)0.015 (2)0.015 (2)
C400.112 (4)0.095 (3)0.059 (3)0.016 (3)0.027 (2)−0.003 (2)
Geometric parameters (Å, °) top
OW—HWB0.8500C20—H20C0.9600
OW—HWA0.8500O4—C211.417 (4)
O1—C11.424 (5)O4—H4C0.8501
O1—H1A0.8499O5—C271.368 (4)
O2—C71.371 (4)O5—C261.417 (4)
O2—C61.436 (4)O6—C381.376 (4)
O3—C181.359 (4)O6—C391.419 (4)
O3—C191.415 (4)N3—N41.234 (4)
N1—N21.234 (4)N3—C301.414 (4)
N1—C101.434 (4)N4—C331.422 (4)
N2—C131.425 (4)C21—C221.492 (5)
C1—C21.497 (5)C21—H21A0.9700
C1—H1C0.9700C21—H21B0.9700
C1—H1D0.9700C22—C231.513 (5)
C2—C31.513 (5)C22—H22A0.9700
C2—H2B0.9700C22—H22B0.9700
C2—H2C0.9700C23—C241.512 (4)
C3—C41.513 (5)C23—H23A0.9700
C3—H3A0.9700C23—H23B0.9700
C3—H3B0.9700C24—C251.511 (5)
C4—C51.516 (5)C24—H24A0.9700
C4—H4A0.9700C24—H24B0.9700
C4—H4B0.9700C25—C261.499 (5)
C5—C61.504 (5)C25—H25A0.9700
C5—H5A0.9700C25—H25B0.9700
C5—H5B0.9700C26—H26A0.9700
C6—H6A0.9700C26—H26B0.9700
C6—H6B0.9700C27—C281.375 (5)
C7—C81.358 (5)C27—C321.378 (5)
C7—C121.388 (5)C28—C291.357 (5)
C8—C91.383 (5)C28—H28A0.9300
C8—H8A0.9300C29—C301.394 (5)
C9—C101.373 (5)C29—H29A0.9300
C9—H9A0.9300C30—C311.359 (5)
C10—C111.364 (5)C31—C321.384 (5)
C11—C121.357 (5)C31—H31A0.9300
C11—H11A0.9300C32—H32A0.9300
C12—H12A0.9300C33—C341.389 (4)
C13—C141.372 (5)C33—C381.393 (5)
C13—C181.399 (5)C34—C351.382 (5)
C14—C151.387 (5)C34—H34A0.9300
C14—H14A0.9300C35—C361.355 (5)
C15—C161.382 (5)C35—H35A0.9300
C15—H15A0.9300C36—C371.397 (5)
C16—C171.365 (5)C36—H36A0.9300
C16—H16A0.9300C37—C381.390 (5)
C17—C181.392 (5)C37—H37A0.9300
C17—H17A0.9300C39—C401.507 (5)
C19—C201.501 (5)C39—H39A0.9700
C19—H19A0.9700C39—H39B0.9700
C19—H19B0.9700C40—H40A0.9600
C20—H20A0.9600C40—H40B0.9600
C20—H20B0.9600C40—H40C0.9600
HWB—OW—HWA106.9C21—O4—H4C106.1
C1—O1—H1A108.6C27—O5—C26120.5 (3)
C7—O2—C6117.8 (3)C38—O6—C39118.1 (3)
C18—O3—C19119.5 (3)N4—N3—C30115.4 (3)
N2—N1—C10112.9 (3)N3—N4—C33114.2 (3)
N1—N2—C13115.5 (3)O4—C21—C22113.7 (4)
O1—C1—C2112.5 (4)O4—C21—H21A108.8
O1—C1—H1C109.1C22—C21—H21A108.8
C2—C1—H1C109.1O4—C21—H21B108.8
O1—C1—H1D109.1C22—C21—H21B108.8
C2—C1—H1D109.1H21A—C21—H21B107.7
H1C—C1—H1D107.8C21—C22—C23115.2 (3)
C1—C2—C3114.5 (3)C21—C22—H22A108.5
C1—C2—H2B108.6C23—C22—H22A108.5
C3—C2—H2B108.6C21—C22—H22B108.5
C1—C2—H2C108.6C23—C22—H22B108.5
C3—C2—H2C108.6H22A—C22—H22B107.5
H2B—C2—H2C107.6C24—C23—C22112.4 (3)
C2—C3—C4113.5 (3)C24—C23—H23A109.1
C2—C3—H3A108.9C22—C23—H23A109.1
C4—C3—H3A108.9C24—C23—H23B109.1
C2—C3—H3B108.9C22—C23—H23B109.1
C4—C3—H3B108.9H23A—C23—H23B107.9
H3A—C3—H3B107.7C25—C24—C23113.7 (3)
C3—C4—C5114.3 (3)C25—C24—H24A108.8
C3—C4—H4A108.7C23—C24—H24A108.8
C5—C4—H4A108.7C25—C24—H24B108.8
C3—C4—H4B108.7C23—C24—H24B108.8
C5—C4—H4B108.7H24A—C24—H24B107.7
H4A—C4—H4B107.6C26—C25—C24113.0 (3)
C6—C5—C4111.9 (3)C26—C25—H25A109.0
C6—C5—H5A109.2C24—C25—H25A109.0
C4—C5—H5A109.2C26—C25—H25B109.0
C6—C5—H5B109.2C24—C25—H25B109.0
C4—C5—H5B109.2H25A—C25—H25B107.8
H5A—C5—H5B107.9O5—C26—C25108.1 (3)
O2—C6—C5107.6 (3)O5—C26—H26A110.1
O2—C6—H6A110.2C25—C26—H26A110.1
C5—C6—H6A110.2O5—C26—H26B110.1
O2—C6—H6B110.2C25—C26—H26B110.1
C5—C6—H6B110.2H26A—C26—H26B108.4
H6A—C6—H6B108.5O5—C27—C28116.0 (3)
C8—C7—O2125.7 (3)O5—C27—C32124.4 (3)
C8—C7—C12118.7 (3)C28—C27—C32119.6 (3)
O2—C7—C12115.6 (3)C29—C28—C27121.1 (4)
C7—C8—C9119.8 (4)C29—C28—H28A119.4
C7—C8—H8A120.1C27—C28—H28A119.4
C9—C8—H8A120.1C28—C29—C30120.2 (3)
C10—C9—C8121.0 (4)C28—C29—H29A119.9
C10—C9—H9A119.5C30—C29—H29A119.9
C8—C9—H9A119.5C31—C30—C29118.2 (3)
C11—C10—C9118.9 (3)C31—C30—N3117.2 (3)
C11—C10—N1124.8 (3)C29—C30—N3124.6 (3)
C9—C10—N1116.3 (3)C30—C31—C32122.3 (4)
C12—C11—C10120.3 (4)C30—C31—H31A118.8
C12—C11—H11A119.9C32—C31—H31A118.8
C10—C11—H11A119.9C27—C32—C31118.5 (4)
C11—C12—C7121.3 (4)C27—C32—H32A120.7
C11—C12—H12A119.4C31—C32—H32A120.7
C7—C12—H12A119.4C34—C33—C38118.6 (3)
C14—C13—C18119.6 (3)C34—C33—N4123.6 (3)
C14—C13—N2124.9 (3)C38—C33—N4117.7 (3)
C18—C13—N2115.4 (3)C35—C34—C33120.8 (4)
C13—C14—C15121.1 (4)C35—C34—H34A119.6
C13—C14—H14A119.4C33—C34—H34A119.6
C15—C14—H14A119.4C36—C35—C34119.9 (4)
C16—C15—C14118.7 (4)C36—C35—H35A120.1
C16—C15—H15A120.6C34—C35—H35A120.1
C14—C15—H15A120.6C35—C36—C37121.5 (4)
C17—C16—C15121.2 (4)C35—C36—H36A119.3
C17—C16—H16A119.4C37—C36—H36A119.3
C15—C16—H16A119.4C38—C37—C36118.3 (4)
C16—C17—C18120.2 (4)C38—C37—H37A120.9
C16—C17—H17A119.9C36—C37—H37A120.9
C18—C17—H17A119.9O6—C38—C37122.8 (3)
O3—C18—C17124.5 (3)O6—C38—C33116.3 (3)
O3—C18—C13116.3 (3)C37—C38—C33120.9 (3)
C17—C18—C13119.2 (3)O6—C39—C40108.2 (3)
O3—C19—C20107.2 (3)O6—C39—H39A110.1
O3—C19—H19A110.3C40—C39—H39A110.1
C20—C19—H19A110.3O6—C39—H39B110.1
O3—C19—H19B110.3C40—C39—H39B110.1
C20—C19—H19B110.3H39A—C39—H39B108.4
H19A—C19—H19B108.5C39—C40—H40A109.5
C19—C20—H20A109.5C39—C40—H40B109.5
C19—C20—H20B109.5H40A—C40—H40B109.5
H20A—C20—H20B109.5C39—C40—H40C109.5
C19—C20—H20C109.5H40A—C40—H40C109.5
H20A—C20—H20C109.5H40B—C40—H40C109.5
H20B—C20—H20C109.5
C10—N1—N2—C13−178.7 (3)C30—N3—N4—C33179.5 (3)
O1—C1—C2—C3−178.4 (3)O4—C21—C22—C23−176.3 (3)
C1—C2—C3—C4−175.2 (3)C21—C22—C23—C24176.3 (4)
C2—C3—C4—C5−178.0 (3)C22—C23—C24—C25−178.0 (3)
C3—C4—C5—C6176.6 (3)C23—C24—C25—C26175.7 (3)
C7—O2—C6—C5178.7 (3)C27—O5—C26—C25−179.4 (3)
C4—C5—C6—O2179.6 (3)C24—C25—C26—O5177.0 (3)
C6—O2—C7—C82.4 (6)C26—O5—C27—C28−176.6 (3)
C6—O2—C7—C12−177.3 (4)C26—O5—C27—C324.0 (6)
O2—C7—C8—C9179.7 (4)O5—C27—C28—C29−179.4 (4)
C12—C7—C8—C9−0.6 (7)C32—C27—C28—C29−0.1 (6)
C7—C8—C9—C100.0 (7)C27—C28—C29—C300.1 (6)
C8—C9—C10—C111.4 (6)C28—C29—C30—C31−0.5 (6)
C8—C9—C10—N1179.9 (4)C28—C29—C30—N3−178.9 (4)
N2—N1—C10—C11−2.5 (5)N4—N3—C30—C31176.6 (4)
N2—N1—C10—C9179.1 (4)N4—N3—C30—C29−5.1 (6)
C9—C10—C11—C12−2.1 (6)C29—C30—C31—C320.8 (7)
N1—C10—C11—C12179.6 (4)N3—C30—C31—C32179.3 (4)
C10—C11—C12—C71.4 (7)O5—C27—C32—C31179.7 (4)
C8—C7—C12—C110.0 (7)C28—C27—C32—C310.4 (6)
O2—C7—C12—C11179.6 (4)C30—C31—C32—C27−0.8 (7)
N1—N2—C13—C145.6 (5)N3—N4—C33—C344.0 (5)
N1—N2—C13—C18−176.5 (3)N3—N4—C33—C38−176.9 (3)
C18—C13—C14—C150.1 (5)C38—C33—C34—C350.7 (5)
N2—C13—C14—C15177.9 (3)N4—C33—C34—C35179.8 (3)
C13—C14—C15—C160.0 (6)C33—C34—C35—C36−0.6 (6)
C14—C15—C16—C170.3 (6)C34—C35—C36—C370.4 (6)
C15—C16—C17—C18−0.6 (6)C35—C36—C37—C38−0.3 (6)
C19—O3—C18—C17−5.3 (5)C39—O6—C38—C37−4.8 (5)
C19—O3—C18—C13173.6 (3)C39—O6—C38—C33174.0 (3)
C16—C17—C18—O3179.5 (3)C36—C37—C38—O6179.2 (3)
C16—C17—C18—C130.7 (5)C36—C37—C38—C330.4 (5)
C14—C13—C18—O3−179.4 (3)C34—C33—C38—O6−179.4 (3)
N2—C13—C18—O32.6 (4)N4—C33—C38—O61.4 (5)
C14—C13—C18—C17−0.4 (5)C34—C33—C38—C37−0.6 (5)
N2—C13—C18—C17−178.5 (3)N4—C33—C38—C37−179.8 (3)
C18—O3—C19—C20−173.9 (3)C38—O6—C39—C40−169.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
OW—HWB···O40.852.322.713 (4)109
OW—HWA···O40.852.312.713 (4)110
O1—H1A···OWi0.852.142.768 (4)130
O4—H4C···O1ii0.852.162.753 (4)127
C15—H15A···O2iii0.932.593.494 (5)166
C35—H35A···O5iii0.932.573.487 (5)170
C40—H40C···OWiv0.962.593.332 (5)134
Symmetry codes: (i) x−1, y, z+1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
OW—HWB···O40.852.322.713 (4)109
OW—HWA···O40.852.312.713 (4)110
O1—H1A···OWi0.852.142.768 (4)130
O4—H4C···O1ii0.852.162.753 (4)127
C15—H15A···O2iii0.932.593.494 (5)166
C35—H35A···O5iii0.932.573.487 (5)170
C40—H40C···OWiv0.962.593.332 (5)134
Symmetry codes: (i) x−1, y, z+1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z.
Acknowledgements top

no

references
References top

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Zhao, X. Y., Hu, X., Yue, C. Y., Xia, X. & Gan, L. H. (2002). Thin Solid Films, 417, 95–100.