organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 9 December 2008; accepted 25 December 2008; online 11 February 2009)

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[Zhao, X. Y., Hu, X., Yue, C. Y., Xia, X. & Gan, L. H. (2002). Thin Solid Films, 417, 95-100.]). For background, see: Bach et al. (1996[Bach, H., Anderle, K., Fuhrmann, Th. & Wendorff, J. H. (1996). J. Phys. Chem. 100, 4135-4140.]).

[Scheme 1]

Experimental

Crystal data
  • 2C20H26N2O3·H2O

  • Mr = 702.87

  • Triclinic, [P \overline 1]

  • 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.956, Tmax = 0.982

  • 7726 measured reflections

  • 7134 independent reflections

  • 3403 reflections with I > 2σ(I)

  • Rint = 0.077

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
OW—HWB⋯O4 0.85 2.32 2.713 (4) 109
OW—HWA⋯O4 0.85 2.31 2.713 (4) 110
O1—H1A⋯OWi 0.85 2.14 2.768 (4) 130
O4—H4C⋯O1ii 0.85 2.16 2.753 (4) 127
C15—H15A⋯O2iii 0.93 2.59 3.494 (5) 166
C35—H35A⋯O5iii 0.93 2.57 3.487 (5) 170
C40—H40C⋯OWiv 0.96 2.59 3.332 (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.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 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 top
Enraf–Nonius CAD-4
diffractometer
3403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
Graphite monochromatorθmax = 25.3°, θmin = 1.7°
ω/2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 1313
Tmin = 0.956, Tmax = 0.982l = 2828
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 Å3
0 restraintsΔρmin = 0.30 e Å3
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 mm1
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 = 0.9823 standard reflections every 200 reflections
7726 measured reflections intensity decay: 1%
7134 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å3
7134 reflectionsΔρmin = 0.30 e Å3
460 parameters
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)
HWB0.45220.85760.25050.117*
HWA0.46670.97340.23390.117*
O10.2094 (4)0.8215 (3)0.72415 (13)0.1066 (11)
H1A0.23900.88730.72490.128*
O20.2623 (4)0.2599 (2)0.47771 (11)0.0815 (8)
O30.2369 (4)0.2649 (2)0.26105 (10)0.0694 (7)
N10.2457 (5)0.2022 (3)0.41759 (13)0.0670 (9)
N20.2520 (4)0.2221 (2)0.36679 (13)0.0592 (8)
C10.2298 (6)0.7803 (4)0.66703 (19)0.0878 (14)
H1C0.12980.83200.64950.105*
H1D0.34950.78640.64720.105*
C20.2224 (6)0.6527 (3)0.66147 (16)0.0724 (11)
H2B0.32420.60140.67840.087*
H2C0.10430.64670.68250.087*
C30.2381 (6)0.6057 (3)0.60160 (16)0.0725 (11)
H3A0.13020.65230.58560.087*
H3B0.35090.61760.57960.087*
C40.2468 (5)0.4737 (3)0.59679 (15)0.0639 (10)
H4A0.35720.42710.61170.077*
H4B0.13630.46150.62000.077*
C50.2556 (6)0.4259 (3)0.53730 (15)0.0674 (10)
H5A0.37030.43270.51440.081*
H5B0.14900.47470.52140.081*
C60.2523 (6)0.2965 (3)0.53547 (15)0.0682 (11)
H6A0.13690.28860.55750.082*
H6B0.35890.24640.55090.082*
C70.2574 (5)0.1447 (3)0.46608 (16)0.0641 (10)
C80.2501 (6)0.0598 (3)0.50434 (16)0.0780 (12)
H8A0.24760.07790.54220.094*
C90.2466 (6)0.0536 (4)0.48678 (16)0.0810 (13)
H9A0.24150.11140.51310.097*
C100.2504 (5)0.0821 (3)0.43104 (15)0.0578 (9)
C110.2537 (6)0.0043 (3)0.39299 (16)0.0712 (11)
H11A0.25220.01290.35530.085*
C120.2592 (6)0.1153 (4)0.40993 (16)0.0804 (13)
H12A0.26430.17280.38340.096*
C130.2518 (5)0.3409 (3)0.35068 (15)0.0527 (9)
C140.2609 (5)0.4337 (3)0.38626 (16)0.0648 (10)
H14A0.26370.41990.42420.078*
C150.2659 (5)0.5478 (3)0.36662 (18)0.0702 (11)
H15A0.27200.61020.39100.084*
C160.2618 (5)0.5669 (4)0.31014 (19)0.0725 (11)
H16A0.26570.64310.29650.087*
C170.2520 (5)0.4757 (3)0.27399 (17)0.0656 (10)
H17A0.24810.49010.23620.079*
C180.2479 (5)0.3613 (3)0.29358 (15)0.0556 (9)
C190.2130 (6)0.2753 (3)0.20418 (15)0.0675 (11)
H19A0.32370.33170.18290.081*
H19B0.10400.30420.20160.081*
C200.1848 (6)0.1522 (4)0.18134 (17)0.0864 (13)
H20A0.16680.15570.14280.130*
H20B0.07550.09720.20290.130*
H20C0.29400.12500.18380.130*
O40.1625 (4)0.8614 (2)0.22791 (12)0.0906 (9)
H4C0.07040.80700.24580.109*
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)
H21A0.06670.83010.15640.102*
H21B0.28570.88740.14940.102*
C220.2088 (6)0.7064 (3)0.16406 (16)0.0707 (11)
H22A0.32610.70650.17690.085*
H22B0.10730.64840.18810.085*
C230.2158 (6)0.6645 (3)0.10461 (16)0.0661 (10)
H23A0.32280.71860.08080.079*
H23B0.10200.66830.09060.079*
C240.2325 (6)0.5374 (3)0.10095 (15)0.0658 (10)
H24A0.12790.48420.12600.079*
H24B0.34840.53460.11390.079*
C250.2330 (6)0.4913 (3)0.04241 (15)0.0664 (10)
H25A0.34310.54070.01790.080*
H25B0.12170.49950.02820.080*
C260.2352 (6)0.3623 (3)0.04032 (15)0.0671 (10)
H26A0.12150.31090.06260.081*
H26B0.34350.35190.05550.081*
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)
H31A0.26870.04220.01190.103*
C320.2589 (7)0.1291 (4)0.00667 (17)0.0846 (13)
H32A0.26010.14360.04460.102*
C330.2824 (5)0.2583 (3)0.14889 (15)0.0536 (9)
C340.2858 (5)0.3467 (3)0.11001 (16)0.0619 (10)
H34A0.28620.32920.07240.074*
C350.2887 (5)0.4604 (3)0.12658 (19)0.0705 (11)
H35A0.28980.51910.10010.085*
C360.2898 (5)0.4861 (3)0.1814 (2)0.0741 (11)
H36A0.29260.56270.19220.089*
C370.2870 (5)0.4001 (3)0.22214 (17)0.0679 (11)
H37A0.28710.41870.25970.081*
C380.2839 (5)0.2860 (3)0.20512 (16)0.0580 (9)
C390.2613 (6)0.2236 (4)0.29842 (15)0.0755 (12)
H39A0.37710.23740.31730.091*
H39B0.15860.29600.29960.091*
C400.2227 (7)0.1189 (4)0.32730 (17)0.0897 (14)
H40A0.21080.13610.36580.135*
H40B0.10750.10620.30850.135*
H40C0.32520.04770.32610.135*
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, º) 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—C13178.7 (3)C30—N3—N4—C33179.5 (3)
O1—C1—C2—C3178.4 (3)O4—C21—C22—C23176.3 (3)
C1—C2—C3—C4175.2 (3)C21—C22—C23—C24176.3 (4)
C2—C3—C4—C5178.0 (3)C22—C23—C24—C25178.0 (3)
C3—C4—C5—C6176.6 (3)C23—C24—C25—C26175.7 (3)
C7—O2—C6—C5178.7 (3)C27—O5—C26—C25179.4 (3)
C4—C5—C6—O2179.6 (3)C24—C25—C26—O5177.0 (3)
C6—O2—C7—C82.4 (6)C26—O5—C27—C28176.6 (3)
C6—O2—C7—C12177.3 (4)C26—O5—C27—C324.0 (6)
O2—C7—C8—C9179.7 (4)O5—C27—C28—C29179.4 (4)
C12—C7—C8—C90.6 (7)C32—C27—C28—C290.1 (6)
C7—C8—C9—C100.0 (7)C27—C28—C29—C300.1 (6)
C8—C9—C10—C111.4 (6)C28—C29—C30—C310.5 (6)
C8—C9—C10—N1179.9 (4)C28—C29—C30—N3178.9 (4)
N2—N1—C10—C112.5 (5)N4—N3—C30—C31176.6 (4)
N2—N1—C10—C9179.1 (4)N4—N3—C30—C295.1 (6)
C9—C10—C11—C122.1 (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—C270.8 (7)
N1—N2—C13—C145.6 (5)N3—N4—C33—C344.0 (5)
N1—N2—C13—C18176.5 (3)N3—N4—C33—C38176.9 (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—C360.6 (6)
C14—C15—C16—C170.3 (6)C34—C35—C36—C370.4 (6)
C15—C16—C17—C180.6 (6)C35—C36—C37—C380.3 (6)
C19—O3—C18—C175.3 (5)C39—O6—C38—C374.8 (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—O3179.4 (3)C34—C33—C38—O6179.4 (3)
N2—C13—C18—O32.6 (4)N4—C33—C38—O61.4 (5)
C14—C13—C18—C170.4 (5)C34—C33—C38—C370.6 (5)
N2—C13—C18—C17178.5 (3)N4—C33—C38—C37179.8 (3)
C18—O3—C19—C20173.9 (3)C38—O6—C39—C40169.8 (3)
Hydrogen-bond geometry (Å, º) 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) x1, y, z+1; (ii) x, y, z1; (iii) x, y1, z; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula2C20H26N2O3·H2O
Mr702.87
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.4586 (7), 11.5674 (11), 24.070 (2)
α, β, γ (°)90.46 (3), 98.46 (3), 106.10 (3)
V3)1970.9 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.956, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
7726, 7134, 3403
Rint0.077
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.181, 1.00
No. of reflections7134
No. of parameters460
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.30

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) 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) x1, y, z+1; (ii) x, y, z1; (iii) x, y1, z; (iv) x+1, y+1, z.
 

References

First citationBach, H., Anderle, K., Fuhrmann, Th. & Wendorff, J. H. (1996). J. Phys. Chem. 100, 4135–4140.  CrossRef CAS Web of Science Google Scholar
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhao, X. Y., Hu, X., Yue, C. Y., Xia, X. & Gan, L. H. (2002). Thin Solid Films, 417, 95–100.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds