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

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

doi:10.1107/S1600536808043924

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o509

doi:10.1107/S1600536808043924

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

Ran-zhe Lu,^a Min Zhang,^a Lu-na Han,^a Bin Wang ^a and Hai-bo Wang ^a ^*

^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 ). For background, see: Bach et al. (1996 ).

Experimental

Crystal data

2C₂₀H₂₆N₂O₃·H₂O
M_r = 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 ) 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[F² > 2σ(F²)] = 0.074
wR(F²) = 0.181
S = 1.00
7134 reflections
460 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯OW^iv	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 ); cell refinement: CAD-4 EXPRESS; 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.

Supporting information

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

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

checkCIF report

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.

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

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·H₂O	Z = 2
M_r = 702.87	F(000) = 756
Triclinic, P1	D_x = 1.184 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4586 (7) Å	Cell parameters from 25 reflections
b = 11.5674 (11) Å	θ = 9–13°
c = 24.070 (2) Å	µ = 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 tube	R_int = 0.077
Graphite monochromator	θ_max = 25.3°, θ_min = 1.7°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
T_min = 0.956, T_max = 0.982	l = −28→28
7726 measured reflections	3 standard reflections every 200 reflections
7134 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.05P)² + 1.3P] where P = (F_o² + 2F_c²)/3
7134 reflections	(Δ/σ)_max < 0.001
460 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

2C₂₀H₂₆N₂O₃·H₂O	γ = 106.10 (3)°
M_r = 702.87	V = 1970.9 (5) Å³
Triclinic, P1	Z = 2
a = 7.4586 (7) Å	Mo Kα radiation
b = 11.5674 (11) Å	µ = 0.08 mm⁻¹
c = 24.070 (2) Å	T = 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)	R_int = 0.077
T_min = 0.956, T_max = 0.982	3 standard reflections every 200 reflections
7726 measured reflections	intensity decay: 1%
7134 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
7134 reflections	Δρ_min = −0.30 e Å⁻³
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

	x	y	z	U_iso*/U_eq
OW	0.5276 (4)	0.9282 (2)	−0.24533 (12)	0.0971 (10)
HWB	0.4522	0.8576	−0.2505	0.117*
HWA	0.4667	0.9734	−0.2339	0.117*
O1	−0.2094 (4)	0.8215 (3)	0.72415 (13)	0.1066 (11)
H1A	−0.2390	0.8873	0.7249	0.128*
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	−0.1298	0.8320	0.6495	0.105*
H1D	−0.3495	0.7864	0.6472	0.105*
C2	−0.2224 (6)	0.6527 (3)	0.66147 (16)	0.0724 (11)
H2B	−0.3242	0.6014	0.6784	0.087*
H2C	−0.1043	0.6467	0.6825	0.087*
C3	−0.2381 (6)	0.6057 (3)	0.60160 (16)	0.0725 (11)
H3A	−0.1302	0.6523	0.5856	0.087*
H3B	−0.3509	0.6176	0.5796	0.087*
C4	−0.2468 (5)	0.4737 (3)	0.59679 (15)	0.0639 (10)
H4A	−0.3572	0.4271	0.6117	0.077*
H4B	−0.1363	0.4615	0.6200	0.077*
C5	−0.2556 (6)	0.4259 (3)	0.53730 (15)	0.0674 (10)
H5A	−0.3703	0.4327	0.5144	0.081*
H5B	−0.1490	0.4747	0.5214	0.081*
C6	−0.2523 (6)	0.2965 (3)	0.53547 (15)	0.0682 (11)
H6A	−0.1369	0.2886	0.5575	0.082*
H6B	−0.3589	0.2464	0.5509	0.082*
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	−0.2476	0.0779	0.5422	0.094*
C9	−0.2466 (6)	−0.0536 (4)	0.48678 (16)	0.0810 (13)
H9A	−0.2415	−0.1114	0.5131	0.097*
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	−0.0129	0.3553	0.085*
C12	−0.2592 (6)	0.1153 (4)	0.40993 (16)	0.0804 (13)
H12A	−0.2643	0.1728	0.3834	0.096*
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	−0.4199	0.4242	0.078*
C15	−0.2659 (5)	−0.5478 (3)	0.36662 (18)	0.0702 (11)
H15A	−0.2720	−0.6102	0.3910	0.084*
C16	−0.2618 (5)	−0.5669 (4)	0.31014 (19)	0.0725 (11)
H16A	−0.2657	−0.6431	0.2965	0.087*
C17	−0.2520 (5)	−0.4757 (3)	0.27399 (17)	0.0656 (10)
H17A	−0.2481	−0.4901	0.2362	0.079*
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	−0.3317	0.1829	0.081*
H19B	−0.1040	−0.3042	0.2016	0.081*
C20	−0.1848 (6)	−0.1522 (4)	0.18134 (17)	0.0864 (13)
H20A	−0.1668	−0.1557	0.1428	0.130*
H20B	−0.0755	−0.0972	0.2029	0.130*
H20C	−0.2940	−0.1250	0.1838	0.130*
O4	0.1625 (4)	0.8614 (2)	−0.22791 (12)	0.0906 (9)
H4C	0.0704	0.8070	−0.2458	0.109*
O5	0.2453 (4)	0.3308 (2)	0.01659 (10)	0.0768 (8)
O6	0.2785 (4)	−0.1956 (2)	0.24180 (10)	0.0668 (7)
N3	0.2699 (5)	−0.1229 (3)	0.08391 (13)	0.0689 (9)
N4	0.2798 (4)	−0.1396 (2)	0.13469 (12)	0.0581 (8)
C21	0.1799 (6)	0.8282 (4)	−0.17127 (19)	0.0852 (13)
H21A	0.0667	0.8301	−0.1564	0.102*
H21B	0.2857	0.8874	−0.1494	0.102*
C22	0.2088 (6)	0.7064 (3)	−0.16406 (16)	0.0707 (11)
H22A	0.3261	0.7065	−0.1769	0.085*
H22B	0.1073	0.6484	−0.1881	0.085*
C23	0.2158 (6)	0.6645 (3)	−0.10461 (16)	0.0661 (10)
H23A	0.3228	0.7186	−0.0808	0.079*
H23B	0.1020	0.6683	−0.0906	0.079*
C24	0.2325 (6)	0.5374 (3)	−0.10095 (15)	0.0658 (10)
H24A	0.1279	0.4842	−0.1260	0.079*
H24B	0.3484	0.5346	−0.1139	0.079*
C25	0.2330 (6)	0.4913 (3)	−0.04241 (15)	0.0664 (10)
H25A	0.3431	0.5407	−0.0179	0.080*
H25B	0.1217	0.4995	−0.0282	0.080*
C26	0.2352 (6)	0.3623 (3)	−0.04032 (15)	0.0671 (10)
H26A	0.1215	0.3109	−0.0626	0.081*
H26B	0.3435	0.3519	−0.0555	0.081*
C27	0.2510 (5)	0.2175 (3)	0.03082 (15)	0.0614 (10)
C28	0.2504 (6)	0.1940 (3)	0.08671 (16)	0.0737 (12)
H28A	0.2452	0.2539	0.1119	0.088*
C29	0.2573 (6)	0.0849 (3)	0.10573 (15)	0.0677 (11)
H29A	0.2566	0.0707	0.1437	0.081*
C30	0.2656 (5)	−0.0058 (3)	0.06852 (15)	0.0616 (10)
C31	0.2649 (7)	0.0181 (4)	0.01333 (16)	0.0855 (14)
H31A	0.2687	−0.0422	−0.0119	0.103*
C32	0.2589 (7)	0.1291 (4)	−0.00667 (17)	0.0846 (13)
H32A	0.2601	0.1436	−0.0446	0.102*
C33	0.2824 (5)	−0.2583 (3)	0.14889 (15)	0.0536 (9)
C34	0.2858 (5)	−0.3467 (3)	0.11001 (16)	0.0619 (10)
H34A	0.2862	−0.3292	0.0724	0.074*
C35	0.2887 (5)	−0.4604 (3)	0.12658 (19)	0.0705 (11)
H35A	0.2898	−0.5191	0.1001	0.085*
C36	0.2898 (5)	−0.4861 (3)	0.1814 (2)	0.0741 (11)
H36A	0.2926	−0.5627	0.1922	0.089*
C37	0.2870 (5)	−0.4001 (3)	0.22214 (17)	0.0679 (11)
H37A	0.2871	−0.4187	0.2597	0.081*
C38	0.2839 (5)	−0.2860 (3)	0.20512 (16)	0.0580 (9)
C39	0.2613 (6)	−0.2236 (4)	0.29842 (15)	0.0755 (12)
H39A	0.3771	−0.2374	0.3173	0.091*
H39B	0.1586	−0.2960	0.2996	0.091*
C40	0.2227 (7)	−0.1189 (4)	0.32730 (17)	0.0897 (14)
H40A	0.2108	−0.1361	0.3658	0.135*
H40B	0.1075	−0.1062	0.3085	0.135*
H40C	0.3252	−0.0477	0.3261	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
OW	0.102 (2)	0.0739 (19)	0.120 (2)	0.0148 (17)	0.0522 (19)	−0.0047 (17)
O1	0.111 (3)	0.095 (2)	0.123 (3)	0.0508 (19)	0.008 (2)	−0.050 (2)
O2	0.128 (3)	0.0624 (17)	0.0648 (18)	0.0391 (17)	0.0244 (16)	−0.0029 (13)
O3	0.097 (2)	0.0609 (16)	0.0555 (16)	0.0248 (15)	0.0232 (14)	−0.0032 (13)
N1	0.089 (2)	0.062 (2)	0.055 (2)	0.0276 (18)	0.0165 (17)	−0.0053 (15)
N2	0.066 (2)	0.0560 (19)	0.059 (2)	0.0185 (15)	0.0193 (16)	−0.0019 (15)
C1	0.091 (3)	0.073 (3)	0.102 (4)	0.031 (3)	0.010 (3)	−0.029 (3)
C2	0.065 (3)	0.073 (3)	0.081 (3)	0.026 (2)	0.006 (2)	−0.019 (2)
C3	0.083 (3)	0.057 (2)	0.081 (3)	0.021 (2)	0.025 (2)	−0.011 (2)
C4	0.065 (3)	0.060 (2)	0.072 (3)	0.0217 (19)	0.018 (2)	−0.0085 (19)
C5	0.083 (3)	0.061 (2)	0.065 (2)	0.029 (2)	0.015 (2)	−0.0009 (19)
C6	0.087 (3)	0.066 (3)	0.055 (2)	0.024 (2)	0.015 (2)	−0.0097 (19)
C7	0.078 (3)	0.052 (2)	0.067 (3)	0.022 (2)	0.020 (2)	−0.008 (2)
C8	0.125 (4)	0.066 (3)	0.052 (2)	0.040 (3)	0.017 (2)	−0.002 (2)
C9	0.130 (4)	0.068 (3)	0.053 (2)	0.038 (3)	0.021 (2)	0.004 (2)
C10	0.063 (2)	0.050 (2)	0.063 (2)	0.0184 (18)	0.0158 (19)	−0.0029 (18)
C11	0.101 (3)	0.063 (3)	0.055 (2)	0.026 (2)	0.024 (2)	−0.004 (2)
C12	0.129 (4)	0.064 (3)	0.057 (3)	0.036 (3)	0.027 (2)	0.002 (2)
C13	0.048 (2)	0.050 (2)	0.063 (2)	0.0176 (17)	0.0127 (17)	−0.0029 (18)
C14	0.071 (3)	0.058 (2)	0.071 (3)	0.022 (2)	0.020 (2)	0.003 (2)
C15	0.071 (3)	0.057 (2)	0.086 (3)	0.022 (2)	0.017 (2)	0.011 (2)
C16	0.073 (3)	0.057 (3)	0.091 (3)	0.023 (2)	0.015 (2)	−0.005 (2)
C17	0.072 (3)	0.057 (2)	0.070 (3)	0.021 (2)	0.013 (2)	−0.010 (2)
C18	0.057 (2)	0.052 (2)	0.058 (2)	0.0153 (18)	0.0094 (18)	0.0027 (18)
C19	0.066 (3)	0.075 (3)	0.061 (2)	0.016 (2)	0.018 (2)	−0.006 (2)
C20	0.100 (4)	0.084 (3)	0.073 (3)	0.015 (3)	0.026 (3)	0.009 (2)
O4	0.089 (2)	0.082 (2)	0.091 (2)	0.0152 (17)	−0.0022 (17)	0.0206 (17)
O5	0.114 (2)	0.0645 (17)	0.0610 (17)	0.0322 (16)	0.0270 (15)	0.0108 (13)
O6	0.0854 (19)	0.0619 (16)	0.0582 (16)	0.0240 (14)	0.0210 (13)	0.0053 (13)
N3	0.100 (3)	0.060 (2)	0.053 (2)	0.0308 (18)	0.0152 (18)	0.0057 (15)
N4	0.065 (2)	0.0559 (19)	0.057 (2)	0.0197 (16)	0.0174 (15)	0.0067 (15)
C21	0.090 (3)	0.078 (3)	0.099 (4)	0.032 (3)	0.037 (3)	0.024 (3)
C22	0.081 (3)	0.062 (2)	0.070 (3)	0.019 (2)	0.019 (2)	0.012 (2)
C23	0.071 (3)	0.059 (2)	0.075 (3)	0.023 (2)	0.020 (2)	0.0070 (19)
C24	0.075 (3)	0.063 (2)	0.069 (3)	0.027 (2)	0.024 (2)	0.0096 (19)
C25	0.075 (3)	0.064 (2)	0.068 (3)	0.029 (2)	0.017 (2)	0.0091 (19)
C26	0.076 (3)	0.069 (3)	0.060 (2)	0.023 (2)	0.019 (2)	0.009 (2)
C27	0.074 (3)	0.055 (2)	0.059 (2)	0.023 (2)	0.013 (2)	0.0095 (19)
C28	0.115 (4)	0.057 (2)	0.060 (3)	0.032 (2)	0.031 (2)	0.007 (2)
C29	0.093 (3)	0.070 (3)	0.047 (2)	0.028 (2)	0.024 (2)	0.0092 (19)
C30	0.074 (3)	0.057 (2)	0.059 (2)	0.023 (2)	0.018 (2)	0.0036 (18)
C31	0.151 (4)	0.069 (3)	0.051 (2)	0.052 (3)	0.021 (3)	0.001 (2)
C32	0.139 (4)	0.072 (3)	0.055 (2)	0.043 (3)	0.029 (3)	0.005 (2)
C33	0.054 (2)	0.047 (2)	0.063 (2)	0.0159 (17)	0.0123 (18)	0.0005 (17)
C34	0.062 (3)	0.062 (2)	0.067 (2)	0.023 (2)	0.0120 (19)	−0.0024 (19)
C35	0.066 (3)	0.058 (3)	0.091 (3)	0.024 (2)	0.011 (2)	−0.009 (2)
C36	0.068 (3)	0.051 (2)	0.104 (3)	0.018 (2)	0.014 (2)	0.008 (2)
C37	0.065 (3)	0.060 (3)	0.080 (3)	0.020 (2)	0.012 (2)	0.011 (2)
C38	0.053 (2)	0.053 (2)	0.070 (3)	0.0146 (18)	0.0137 (19)	−0.0017 (19)
C39	0.084 (3)	0.086 (3)	0.056 (3)	0.022 (2)	0.015 (2)	0.015 (2)
C40	0.112 (4)	0.095 (3)	0.059 (3)	0.016 (3)	0.027 (2)	−0.003 (2)

Geometric parameters (Å, º) top

OW—HWB	0.8500	C20—H20C	0.9600
OW—HWA	0.8500	O4—C21	1.417 (4)
O1—C1	1.424 (5)	O4—H4C	0.8501
O1—H1A	0.8499	O5—C27	1.368 (4)
O2—C7	1.371 (4)	O5—C26	1.417 (4)
O2—C6	1.436 (4)	O6—C38	1.376 (4)
O3—C18	1.359 (4)	O6—C39	1.419 (4)
O3—C19	1.415 (4)	N3—N4	1.234 (4)
N1—N2	1.234 (4)	N3—C30	1.414 (4)
N1—C10	1.434 (4)	N4—C33	1.422 (4)
N2—C13	1.425 (4)	C21—C22	1.492 (5)
C1—C2	1.497 (5)	C21—H21A	0.9700
C1—H1C	0.9700	C21—H21B	0.9700
C1—H1D	0.9700	C22—C23	1.513 (5)
C2—C3	1.513 (5)	C22—H22A	0.9700
C2—H2B	0.9700	C22—H22B	0.9700
C2—H2C	0.9700	C23—C24	1.512 (4)
C3—C4	1.513 (5)	C23—H23A	0.9700
C3—H3A	0.9700	C23—H23B	0.9700
C3—H3B	0.9700	C24—C25	1.511 (5)
C4—C5	1.516 (5)	C24—H24A	0.9700
C4—H4A	0.9700	C24—H24B	0.9700
C4—H4B	0.9700	C25—C26	1.499 (5)
C5—C6	1.504 (5)	C25—H25A	0.9700
C5—H5A	0.9700	C25—H25B	0.9700
C5—H5B	0.9700	C26—H26A	0.9700
C6—H6A	0.9700	C26—H26B	0.9700
C6—H6B	0.9700	C27—C28	1.375 (5)
C7—C8	1.358 (5)	C27—C32	1.378 (5)
C7—C12	1.388 (5)	C28—C29	1.357 (5)
C8—C9	1.383 (5)	C28—H28A	0.9300
C8—H8A	0.9300	C29—C30	1.394 (5)
C9—C10	1.373 (5)	C29—H29A	0.9300
C9—H9A	0.9300	C30—C31	1.359 (5)
C10—C11	1.364 (5)	C31—C32	1.384 (5)
C11—C12	1.357 (5)	C31—H31A	0.9300
C11—H11A	0.9300	C32—H32A	0.9300
C12—H12A	0.9300	C33—C34	1.389 (4)
C13—C14	1.372 (5)	C33—C38	1.393 (5)
C13—C18	1.399 (5)	C34—C35	1.382 (5)
C14—C15	1.387 (5)	C34—H34A	0.9300
C14—H14A	0.9300	C35—C36	1.355 (5)
C15—C16	1.382 (5)	C35—H35A	0.9300
C15—H15A	0.9300	C36—C37	1.397 (5)
C16—C17	1.365 (5)	C36—H36A	0.9300
C16—H16A	0.9300	C37—C38	1.390 (5)
C17—C18	1.392 (5)	C37—H37A	0.9300
C17—H17A	0.9300	C39—C40	1.507 (5)
C19—C20	1.501 (5)	C39—H39A	0.9700
C19—H19A	0.9700	C39—H39B	0.9700
C19—H19B	0.9700	C40—H40A	0.9600
C20—H20A	0.9600	C40—H40B	0.9600
C20—H20B	0.9600	C40—H40C	0.9600

HWB—OW—HWA	106.9	C21—O4—H4C	106.1
C1—O1—H1A	108.6	C27—O5—C26	120.5 (3)
C7—O2—C6	117.8 (3)	C38—O6—C39	118.1 (3)
C18—O3—C19	119.5 (3)	N4—N3—C30	115.4 (3)
N2—N1—C10	112.9 (3)	N3—N4—C33	114.2 (3)
N1—N2—C13	115.5 (3)	O4—C21—C22	113.7 (4)
O1—C1—C2	112.5 (4)	O4—C21—H21A	108.8
O1—C1—H1C	109.1	C22—C21—H21A	108.8
C2—C1—H1C	109.1	O4—C21—H21B	108.8
O1—C1—H1D	109.1	C22—C21—H21B	108.8
C2—C1—H1D	109.1	H21A—C21—H21B	107.7
H1C—C1—H1D	107.8	C21—C22—C23	115.2 (3)
C1—C2—C3	114.5 (3)	C21—C22—H22A	108.5
C1—C2—H2B	108.6	C23—C22—H22A	108.5
C3—C2—H2B	108.6	C21—C22—H22B	108.5
C1—C2—H2C	108.6	C23—C22—H22B	108.5
C3—C2—H2C	108.6	H22A—C22—H22B	107.5
H2B—C2—H2C	107.6	C24—C23—C22	112.4 (3)
C2—C3—C4	113.5 (3)	C24—C23—H23A	109.1
C2—C3—H3A	108.9	C22—C23—H23A	109.1
C4—C3—H3A	108.9	C24—C23—H23B	109.1
C2—C3—H3B	108.9	C22—C23—H23B	109.1
C4—C3—H3B	108.9	H23A—C23—H23B	107.9
H3A—C3—H3B	107.7	C25—C24—C23	113.7 (3)
C3—C4—C5	114.3 (3)	C25—C24—H24A	108.8
C3—C4—H4A	108.7	C23—C24—H24A	108.8
C5—C4—H4A	108.7	C25—C24—H24B	108.8
C3—C4—H4B	108.7	C23—C24—H24B	108.8
C5—C4—H4B	108.7	H24A—C24—H24B	107.7
H4A—C4—H4B	107.6	C26—C25—C24	113.0 (3)
C6—C5—C4	111.9 (3)	C26—C25—H25A	109.0
C6—C5—H5A	109.2	C24—C25—H25A	109.0
C4—C5—H5A	109.2	C26—C25—H25B	109.0
C6—C5—H5B	109.2	C24—C25—H25B	109.0
C4—C5—H5B	109.2	H25A—C25—H25B	107.8
H5A—C5—H5B	107.9	O5—C26—C25	108.1 (3)
O2—C6—C5	107.6 (3)	O5—C26—H26A	110.1
O2—C6—H6A	110.2	C25—C26—H26A	110.1
C5—C6—H6A	110.2	O5—C26—H26B	110.1
O2—C6—H6B	110.2	C25—C26—H26B	110.1
C5—C6—H6B	110.2	H26A—C26—H26B	108.4
H6A—C6—H6B	108.5	O5—C27—C28	116.0 (3)
C8—C7—O2	125.7 (3)	O5—C27—C32	124.4 (3)
C8—C7—C12	118.7 (3)	C28—C27—C32	119.6 (3)
O2—C7—C12	115.6 (3)	C29—C28—C27	121.1 (4)
C7—C8—C9	119.8 (4)	C29—C28—H28A	119.4
C7—C8—H8A	120.1	C27—C28—H28A	119.4
C9—C8—H8A	120.1	C28—C29—C30	120.2 (3)
C10—C9—C8	121.0 (4)	C28—C29—H29A	119.9
C10—C9—H9A	119.5	C30—C29—H29A	119.9
C8—C9—H9A	119.5	C31—C30—C29	118.2 (3)
C11—C10—C9	118.9 (3)	C31—C30—N3	117.2 (3)
C11—C10—N1	124.8 (3)	C29—C30—N3	124.6 (3)
C9—C10—N1	116.3 (3)	C30—C31—C32	122.3 (4)
C12—C11—C10	120.3 (4)	C30—C31—H31A	118.8
C12—C11—H11A	119.9	C32—C31—H31A	118.8
C10—C11—H11A	119.9	C27—C32—C31	118.5 (4)
C11—C12—C7	121.3 (4)	C27—C32—H32A	120.7
C11—C12—H12A	119.4	C31—C32—H32A	120.7
C7—C12—H12A	119.4	C34—C33—C38	118.6 (3)
C14—C13—C18	119.6 (3)	C34—C33—N4	123.6 (3)
C14—C13—N2	124.9 (3)	C38—C33—N4	117.7 (3)
C18—C13—N2	115.4 (3)	C35—C34—C33	120.8 (4)
C13—C14—C15	121.1 (4)	C35—C34—H34A	119.6
C13—C14—H14A	119.4	C33—C34—H34A	119.6
C15—C14—H14A	119.4	C36—C35—C34	119.9 (4)
C16—C15—C14	118.7 (4)	C36—C35—H35A	120.1
C16—C15—H15A	120.6	C34—C35—H35A	120.1
C14—C15—H15A	120.6	C35—C36—C37	121.5 (4)
C17—C16—C15	121.2 (4)	C35—C36—H36A	119.3
C17—C16—H16A	119.4	C37—C36—H36A	119.3
C15—C16—H16A	119.4	C38—C37—C36	118.3 (4)
C16—C17—C18	120.2 (4)	C38—C37—H37A	120.9
C16—C17—H17A	119.9	C36—C37—H37A	120.9
C18—C17—H17A	119.9	O6—C38—C37	122.8 (3)
O3—C18—C17	124.5 (3)	O6—C38—C33	116.3 (3)
O3—C18—C13	116.3 (3)	C37—C38—C33	120.9 (3)
C17—C18—C13	119.2 (3)	O6—C39—C40	108.2 (3)
O3—C19—C20	107.2 (3)	O6—C39—H39A	110.1
O3—C19—H19A	110.3	C40—C39—H39A	110.1
C20—C19—H19A	110.3	O6—C39—H39B	110.1
O3—C19—H19B	110.3	C40—C39—H39B	110.1
C20—C19—H19B	110.3	H39A—C39—H39B	108.4
H19A—C19—H19B	108.5	C39—C40—H40A	109.5
C19—C20—H20A	109.5	C39—C40—H40B	109.5
C19—C20—H20B	109.5	H40A—C40—H40B	109.5
H20A—C20—H20B	109.5	C39—C40—H40C	109.5
C19—C20—H20C	109.5	H40A—C40—H40C	109.5
H20A—C20—H20C	109.5	H40B—C40—H40C	109.5
H20B—C20—H20C	109.5

C10—N1—N2—C13	−178.7 (3)	C30—N3—N4—C33	179.5 (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—C24	176.3 (4)
C2—C3—C4—C5	−178.0 (3)	C22—C23—C24—C25	−178.0 (3)
C3—C4—C5—C6	176.6 (3)	C23—C24—C25—C26	175.7 (3)
C7—O2—C6—C5	178.7 (3)	C27—O5—C26—C25	−179.4 (3)
C4—C5—C6—O2	179.6 (3)	C24—C25—C26—O5	177.0 (3)
C6—O2—C7—C8	2.4 (6)	C26—O5—C27—C28	−176.6 (3)
C6—O2—C7—C12	−177.3 (4)	C26—O5—C27—C32	4.0 (6)
O2—C7—C8—C9	179.7 (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—C10	0.0 (7)	C27—C28—C29—C30	0.1 (6)
C8—C9—C10—C11	1.4 (6)	C28—C29—C30—C31	−0.5 (6)
C8—C9—C10—N1	179.9 (4)	C28—C29—C30—N3	−178.9 (4)
N2—N1—C10—C11	−2.5 (5)	N4—N3—C30—C31	176.6 (4)
N2—N1—C10—C9	179.1 (4)	N4—N3—C30—C29	−5.1 (6)
C9—C10—C11—C12	−2.1 (6)	C29—C30—C31—C32	0.8 (7)
N1—C10—C11—C12	179.6 (4)	N3—C30—C31—C32	179.3 (4)
C10—C11—C12—C7	1.4 (7)	O5—C27—C32—C31	179.7 (4)
C8—C7—C12—C11	0.0 (7)	C28—C27—C32—C31	0.4 (6)
O2—C7—C12—C11	179.6 (4)	C30—C31—C32—C27	−0.8 (7)
N1—N2—C13—C14	5.6 (5)	N3—N4—C33—C34	4.0 (5)
N1—N2—C13—C18	−176.5 (3)	N3—N4—C33—C38	−176.9 (3)
C18—C13—C14—C15	0.1 (5)	C38—C33—C34—C35	0.7 (5)
N2—C13—C14—C15	177.9 (3)	N4—C33—C34—C35	179.8 (3)
C13—C14—C15—C16	0.0 (6)	C33—C34—C35—C36	−0.6 (6)
C14—C15—C16—C17	0.3 (6)	C34—C35—C36—C37	0.4 (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—C13	173.6 (3)	C39—O6—C38—C33	174.0 (3)
C16—C17—C18—O3	179.5 (3)	C36—C37—C38—O6	179.2 (3)
C16—C17—C18—C13	0.7 (5)	C36—C37—C38—C33	0.4 (5)
C14—C13—C18—O3	−179.4 (3)	C34—C33—C38—O6	−179.4 (3)
N2—C13—C18—O3	2.6 (4)	N4—C33—C38—O6	1.4 (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, º) top

D—H···A	D—H	H···A	D···A	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···OW^iv	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.

Experimental details

Crystal data
Chemical formula	2C₂₀H₂₆N₂O₃·H₂O
M_r	702.87
Crystal system, space group	Triclinic, 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)
V (Å³)	1970.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.956, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	7726, 7134, 3403
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.181, 1.00
No. of reflections	7134
No. of parameters	460
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···OW^iv	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.

References

Bach, H., Anderle, K., Fuhrmann, Th. & Wendorff, J. H. (1996). J. Phys. Chem. 100, 4135–4140. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, 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

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Volume 65| Part 3| March 2009| Page o509

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