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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o509.
Published online 2009 February 11. doi:  10.1107/S1600536808043924
PMCID: PMC2968466

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

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0o509-scheme1.jpg

Experimental

Crystal data

  • 2C20H26N2O3·H2O
  • M r = 702.87
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o509-efi1.jpg
  • a = 7.4586 (7) Å
  • b = 11.5674 (11) Å
  • c = 24.070 (2) Å
  • α = 90.46 (3)°
  • β = 98.46 (3)°
  • γ = 106.10 (3)°
  • V = 1970.9 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.956, T max = 0.982
  • 7726 measured reflections
  • 7134 independent reflections
  • 3403 reflections with I > 2σ(I)
  • R int = 0.077
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.181
  • S = 1.00
  • 7134 reflections
  • 460 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.30 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043924/hb2877sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043924/hb2877Isup2.hkl

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level. Dashed lines indicate hydrogen bonds.

Crystal data

2C20H26N2O3·H2OZ = 2
Mr = 702.87F(000) = 756
Triclinic, P1Dx = 1.184 Mg m3
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 mm1
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

Enraf–Nonius CAD-4 diffractometer3403 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

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 = 1.00w = 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 Å3
0 restraintsΔρmin = −0.30 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
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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2877).

References

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  • Enraf–Nonius (1994). CAD-4 EXPRESS Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhao, X. Y., Hu, X., Yue, C. Y., Xia, X. & Gan, L. H. (2002). Thin Solid Films, 417, 95–100.

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