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The title compound, C44H54N2O8·4H2O, has twofold crystallographic symmetry and consists of a calix­[4]­arene moiety with four phenyl rings arranged alternately in anti-orientation fashion and two aza­crown units attached on the lower rims of calix­[4]­arene. This seems to offer a big cavity inside the mol­ecule which might possess a potential for forming host-guest complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199016327/na1433sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016327/na1433Isup2.hkl
Contains datablock I

CCDC reference: 143269

Comment top

Calix[4]arenes have been of particular interest as organic hosts and selective ionophores in inclusion complexation (Gutsche, 1989) and it is known that the calix[4]arenes are able to exist in the following four different conformations: cone (Guelzim et al., 1997; Harkema et al., 1998), partial cone (Kim et al., 1993), 1,2-alternate and 1,3-alternate (Ungaro & Pochini, 1991). In order to investigate the characteristics of the calix[4]arene compounds, a series of calix[4]arene derivatives has been synthesized and their structures elucidated (Kim et al., 1997; Kim, Pang et al., 1998; Kim, Yu et al., 1998; Kim, Suh et al., 1998; Kim, Kim, Lee et al., 1999; Kim, Kim, Choo et al., 1999).

In the title compound, (I), a half molecule belongs to an asymmetric unit and a molecule is completed by another half primed molecule translated by twofold symmetry along the b axis [symmetry code: (i) 1 - x, y, 1/2 - z] (Fig. 1). \sch

(I) consists of the calix[4]arene molecule adopting the 1,3-alternate conformation: two phenyl groups A and B' lie above and the other two phenyl groups A' and B below the least-squares plane defined by the four bridging methylene groups as clearly illustrated in Figure 1, two azacrown units: one of them bonded to phenyl rings A and B' and another one to phenyl rings A' and B, respectively, and four water molecules not represented in the Figure.

The aromatic Csp2– Csp2 distances in the molecule vary from 1.367 (5) to 1.397 (5) Å with an average value of 1.385 (1) Å, Csp2—Csp3 distances from 1.511 (4) to 1.522 (4) Å with a mean value of 1.516 (2) Å, Csp3—Csp3 distances from 1.480 (5) to 1.490 (5) Å with a mean value of 1.485 (3) Å, O-Csp3 distances from 1.377 (4) to 1.438 (4) Å with a mean value of 1.414 (2) Å, and a mean value of two O-Csp2 bonds is 1.383 (3) Å. All of these are very close to those in 25,27-bis(1-propyloxy)calix[4]arene- 26,28-[(5',6')(14',15')-dibenzo]crown-7 (Kim, Pang et al., 1999) and in 1,3-alternate calix[4]arenebiscrown-7 (Khrifi et al., 1997).

Bond angles involving the bridging methylenes C2—C3—C2' = 113.7 (4), C7—C8—C9 = 114.4 (3) and C13—C14—C13' = 114.6 (4)° are quite larger than the tetrahedral angle due to repulsions among the four phenyl groups.

Two adjacent phenyl rings in the calix[4]arene are perpendicular to each other with dihedral angle of A—B = 89.76 (8)° so that the calix[4]arene has a fairly perfect square cavity. However, two facing rings A and B' are slightly splayed out upwards from the central axis with a dihedral angle of 11.6 (2)° leading to C1···C15' 5.337 (4) and C5···C11' 5.870 (5) Å, and the same for the pair facing rings A' and B because of symmetry.

In the azacrown unit, O···O and N···O distances are O1···O2' 5.135 (3), O3···O4' 5.311 (4), N···O1' 4.742 (4) and N···O2 4.800 (4) Å, so that the somewhat flexible cavity lined with four oxygen atoms and a nitrogen atom might enable the molecule to introduce a guest atom. Additionally the torsion angles of O2—C16—C17—O3 and O4—C22—C23—O1 in the azacrown unit are both gauche being -58.5 (5) and 59.9 (4)°, respectively.

There are four hydrogen bonds involving the N atom in the amine group and the two water molecules in an asymmetric unit and it is especially worth mentioning that two water oxygen atoms donate and accept their hydrogen atoms with each other as shown in Table 1, where the distances between H2W1····H1W2 and H2W2····H2W2 (2 - x, -y, 1 - z) are 1.76 and 1.74 Å, respectively. This hydrogen-bond scheme makes an infinite molecular chain running in the [201] direction and the closest contact between the molecular chains is OW1···HC3 (1/2 + x, -1/2 + y, 1/2 - z) = 2.51 Å.

Experimental top

Under nitrogen, into a three-neck round-bottom flask, K2CO3 (0.96 g, 6.95 mmol), pre-dried N,N-dimethylformamide (DMF) (60 ml), 25,26,27,28-tetra(5-chloro-3-oxapentyloxy)calix[4]arene (5.00 g, 5.88 mmol), and p-toluenesulfonamide (2.11 g, 12.3 mmol) were placed and refluxed for 24 h. DMF was completely removed in vacuo and 10% NaHCO3 aqueous solution (100 ml) and CH2Cl2 (100 ml) were added and then the organic layer was separated. The organic layer was washed with water (2 x 50 ml) and dried over anhydrous MgSO4 and filtered. Evaporation of the CH2Cl2 in vacuo gave a yellowish oil which was purified by column chromatography (Rf 0.3) using ethyl acetate: hexane (1:8) to provide 4.00 g (65%) of N-tosyl calix[4]arene bis(azacrown-5) as a white solid (m.p. 421–424 K). To a solution of 1,4-dioxane (100 ml) and methanol (20 ml) were carefully added N-tosyl calix[4]arene bisazacrown-5 (3.00 g, 2.86 mmol) and 6% Na(Hg) amalgam (0.853 g). The reaction mixture refluxed for 2 d at 353 K. After cooling to room temperature the solvent was evaporated in vacuo. CH2Cl2 (50 ml) and water (50 ml) were added and the organic layer was separated. The CH2Cl2 layer was washed twice with 10% Na2HPO4 aqueous solution followed by drying over anhydrous MgSO4. After filtration of magnesium sulfate, removal of the solvent in vacuo gave calix[4]arene bis(azacrown-5) as a white solid which can be recrystallized with diethyl ether (30 ml) (m.p. 458–461 K, 52% yield). IR (KBr pellet, cm-1): 2926, 1456, 1359, 1176, 1094, 928, 767, 664. 1H NMR (CDCl3, p.p.m.): delta 7.18–6.64 (m, 12 H, Ar—H), 3.88 (s, 8 H, ArCH2Ar), 3.67–3.46 (m, 24 H, –CH2–), 2.81(s, 8 H, –OCH2CH2NCH2–): p.p.m. 157.3,134.6, 131.8, 122.7, 71.7, 71.4, 70.9, 49.6, 38.5. FAB MS m/z (M+) calculated 738.9, found 739.1.

Refinement top

An H atom of the amine group and those of C3 and C14 sat on a twofold axis could be located from a difference Fourier map and the positions of the four hydrogen atoms of two water molecules were calculated by the program HYDROGEN (Nardelli, 1999), and their positions were fixed with Uiso (H) = 1.2Ueq (N, C, O), while all other H atoms were placed in calculated positions and allowed to ride upon the carbon atoms with Uiso (H) = 1.2Ueq (C).

Computing details top

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Johnson, 1976); software used to prepare material for publication: WinGX publication routines (Farrugia, 1998).

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1976) drawing of (I) with atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. The unprimed atoms belong to an asymmetric unit and a molecule is completed by another primed asymmetric unit translated by a symmetry code, 1 - x, y, 0.5 - z. Phenyl rings A and B' are slightly splayed out upwards. The oxygen and nitrogen atoms are expressed with ellipsoids with octant shading, and water molecules and H atoms are omitted for clarity.
(I) top
Crystal data top
C44H54N2O8·4H2ODx = 1.225 Mg m3
Mr = 810.96Mo Kα radiation, λ = 0.71069 Å
Orthorhombic, PbcnCell parameters from 25 reflections
a = 15.922 (2) Åθ = 11.0–12.5°
b = 16.7908 (16) ŵ = 0.09 mm1
c = 16.453 (4) ÅT = 288 K
V = 4398.6 (13) Å3Block, colorless
Z = 40.73 × 0.59 × 0.59 mm
F(000) = 1744
Data collection top
Enraf Nonius CAD4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 018
non–profiled ω/2θ scansk = 019
4330 measured reflectionsl = 190
3861 independent reflections3 standard reflections every 300 min
2185 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 0.99Calculated w = 1/[σ2(Fo2) + (0.0944P)2 + 2.5719P]
where P = (Fo2 + 2Fc2)/3
3861 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C44H54N2O8·4H2OV = 4398.6 (13) Å3
Mr = 810.96Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 15.922 (2) ŵ = 0.09 mm1
b = 16.7908 (16) ÅT = 288 K
c = 16.453 (4) Å0.73 × 0.59 × 0.59 mm
Data collection top
Enraf Nonius CAD4
diffractometer
Rint = 0.000
4330 measured reflections3 standard reflections every 300 min
3861 independent reflections intensity decay: 2%
2185 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.55 e Å3
3861 reflectionsΔρmin = 0.26 e Å3
263 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
N0.83325 (17)0.19262 (18)0.21232 (18)0.0564 (8)
HN0.77240.19560.21390.068*
O10.40432 (14)0.29323 (13)0.14743 (13)0.0477 (6)
O20.57001 (14)0.07666 (13)0.13362 (14)0.0506 (6)
O30.73809 (15)0.09153 (15)0.09413 (15)0.0638 (7)
O40.23551 (15)0.32006 (17)0.18414 (16)0.0710 (8)
C10.4904 (2)0.29852 (18)0.13584 (19)0.0436 (8)
C20.5380 (2)0.35139 (19)0.1824 (2)0.0486 (8)
C30.50000.4006 (3)0.25000.0540 (13)
HC30.45310.44230.22640.065*
C40.6235 (2)0.3552 (2)0.1657 (2)0.0610 (10)
HC40.65690.39080.19460.073*
C50.6599 (2)0.3078 (3)0.1075 (3)0.0682 (11)
HC50.71700.31260.09640.082*
C60.6124 (2)0.2537 (2)0.0658 (2)0.0630 (11)
HC60.63800.22040.02800.076*
C70.5266 (2)0.2476 (2)0.0788 (2)0.0494 (9)
C80.4745 (2)0.1864 (2)0.0340 (2)0.0593 (10)
HC8A0.50990.16010.00580.071*
HC8B0.43020.21370.00470.071*
C90.4351 (2)0.1235 (2)0.0880 (2)0.0497 (9)
C100.3484 (2)0.1151 (2)0.0914 (2)0.0605 (10)
HC100.31500.14710.05860.073*
C110.3108 (2)0.0607 (2)0.1418 (3)0.0655 (11)
HC110.25270.05490.14190.079*
C120.3599 (2)0.0146 (2)0.1924 (2)0.0601 (10)
HC120.33430.02150.22740.072*
C130.4464 (2)0.02107 (19)0.1919 (2)0.0501 (9)
C140.50000.0279 (3)0.25000.0599 (14)
HC140.46030.06750.28010.072*
C150.4835 (2)0.07318 (18)0.1368 (2)0.0444 (8)
C160.6072 (2)0.0311 (3)0.0689 (3)0.0702 (12)
H16A0.60070.05930.01780.084*
H16B0.57900.01990.06430.084*
C170.6975 (2)0.0186 (2)0.0861 (3)0.0696 (12)
H17A0.70370.01190.13590.084*
H17B0.72280.01160.04220.084*
C180.8247 (2)0.0836 (2)0.1134 (2)0.0622 (11)
H18A0.85470.06020.06800.075*
H18B0.83160.04920.16030.075*
C190.8584 (2)0.1642 (2)0.1314 (2)0.0630 (10)
H19A0.91930.16280.12820.076*
H19B0.83840.20130.09060.076*
C200.8704 (2)0.2694 (2)0.2325 (3)0.0668 (11)
H20A0.85000.30930.19470.080*
H20B0.93090.26610.22650.080*
C210.1500 (2)0.2947 (2)0.1834 (3)0.0702 (12)
H21A0.14260.25060.14600.084*
H21B0.11360.33800.16670.084*
C220.2670 (2)0.3332 (3)0.1074 (2)0.0701 (12)
H22A0.23520.37540.08140.084*
H22B0.26050.28530.07510.084*
C230.3575 (2)0.3559 (2)0.1102 (2)0.0630 (11)
H23A0.37810.36520.05560.076*
H23B0.36420.40460.14120.076*
OW10.9337 (2)0.08721 (18)0.30622 (19)0.0895 (10)
H1W10.90030.11330.27460.107*
H2W10.90280.04960.32700.107*
OW20.9462 (3)0.0594 (2)0.47177 (19)0.1154 (13)
H1W20.95010.07150.42100.138*
H2W20.95310.00830.47380.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0451 (16)0.0609 (19)0.0630 (19)0.0039 (14)0.0002 (14)0.0018 (16)
O10.0504 (14)0.0452 (13)0.0475 (13)0.0034 (11)0.0032 (11)0.0050 (11)
O20.0478 (14)0.0540 (14)0.0501 (14)0.0019 (11)0.0031 (11)0.0147 (11)
O30.0529 (16)0.0665 (17)0.0721 (18)0.0063 (13)0.0026 (13)0.0025 (14)
O40.0557 (17)0.087 (2)0.0707 (18)0.0031 (14)0.0090 (14)0.0063 (15)
C10.0469 (19)0.0437 (18)0.0402 (17)0.0018 (16)0.0009 (15)0.0148 (16)
C20.055 (2)0.0423 (19)0.049 (2)0.0025 (17)0.0049 (17)0.0150 (16)
C30.068 (3)0.039 (3)0.055 (3)0.0000.009 (3)0.000
C40.062 (2)0.059 (2)0.061 (2)0.013 (2)0.008 (2)0.018 (2)
C50.054 (2)0.082 (3)0.069 (3)0.001 (2)0.009 (2)0.022 (2)
C60.064 (3)0.073 (3)0.052 (2)0.010 (2)0.011 (2)0.011 (2)
C70.060 (2)0.050 (2)0.0381 (18)0.0057 (17)0.0015 (17)0.0091 (16)
C80.071 (2)0.066 (2)0.0411 (19)0.013 (2)0.0044 (18)0.0031 (18)
C90.058 (2)0.049 (2)0.0428 (19)0.0076 (17)0.0097 (17)0.0126 (16)
C100.057 (2)0.060 (2)0.065 (3)0.012 (2)0.018 (2)0.017 (2)
C110.049 (2)0.069 (3)0.079 (3)0.001 (2)0.009 (2)0.016 (2)
C120.059 (2)0.052 (2)0.069 (3)0.0110 (19)0.002 (2)0.009 (2)
C130.057 (2)0.0392 (19)0.055 (2)0.0028 (16)0.0065 (18)0.0099 (16)
C140.066 (3)0.041 (3)0.073 (4)0.0000.006 (3)0.000
C150.044 (2)0.0414 (18)0.0472 (19)0.0009 (15)0.0066 (16)0.0174 (16)
C160.061 (2)0.076 (3)0.074 (3)0.009 (2)0.003 (2)0.034 (2)
C170.063 (3)0.073 (3)0.073 (3)0.013 (2)0.004 (2)0.025 (2)
C180.054 (2)0.069 (3)0.063 (2)0.0112 (19)0.0025 (19)0.002 (2)
C190.056 (2)0.076 (3)0.057 (2)0.002 (2)0.0065 (19)0.008 (2)
C200.051 (2)0.067 (2)0.083 (3)0.009 (2)0.005 (2)0.005 (2)
C210.053 (2)0.066 (3)0.092 (3)0.004 (2)0.014 (2)0.009 (2)
C220.069 (3)0.084 (3)0.058 (2)0.018 (2)0.010 (2)0.009 (2)
C230.061 (2)0.069 (2)0.059 (2)0.011 (2)0.0058 (19)0.021 (2)
OW10.101 (2)0.088 (2)0.079 (2)0.0274 (18)0.0023 (17)0.0165 (17)
OW20.179 (4)0.103 (3)0.065 (2)0.027 (3)0.009 (2)0.0020 (19)
Geometric parameters (Å, º) top
N—C201.457 (4)C6—C71.386 (5)
N—C191.471 (5)C7—C81.513 (5)
O1—C11.386 (4)C8—C91.516 (5)
O1—C231.428 (4)C9—C101.389 (5)
O2—C151.380 (4)C9—C151.397 (5)
O2—C161.438 (4)C10—C111.371 (5)
O3—C171.392 (4)C11—C121.379 (5)
O3—C181.421 (4)C12—C131.382 (5)
O4—C221.377 (4)C13—C151.392 (5)
O4—C211.427 (4)C13—C14i1.522 (4)
C1—C21.397 (4)C13—C141.522 (4)
C1—C71.395 (4)C14—C13i1.522 (4)
C2—C41.392 (5)C16—C171.480 (5)
C2—C31.511 (4)C18—C191.486 (5)
C3—C2i1.511 (4)C20—C21i1.482 (6)
C4—C51.374 (5)C21—C20i1.482 (6)
C5—C61.367 (5)C22—C231.490 (5)
C20—N—C19112.5 (3)C15—C9—C8122.0 (3)
C1—O1—C23114.2 (2)C11—C10—C9121.8 (4)
C15—O2—C16114.6 (3)C10—C11—C12119.4 (4)
C17—O3—C18112.9 (3)C11—C12—C13121.2 (4)
C22—O4—C21112.8 (3)C12—C13—C15118.4 (3)
O1—C1—C2120.1 (3)C12—C13—C14i120.9 (3)
O1—C1—C7117.5 (3)C15—C13—C14i120.7 (3)
C2—C1—C7122.3 (3)C12—C13—C14120.9 (3)
C4—C2—C1116.9 (3)C15—C13—C14120.7 (3)
C4—C2—C3120.8 (3)C13i—C14—C13114.6 (4)
C1—C2—C3122.3 (3)O2—C15—C13118.3 (3)
C2—C3—C2i113.7 (4)O2—C15—C9120.2 (3)
C5—C4—C2121.6 (4)C13—C15—C9121.4 (3)
C6—C5—C4120.1 (4)O2—C16—C17109.5 (3)
C5—C6—C7121.1 (4)O3—C17—C16110.1 (3)
C6—C7—C1117.8 (3)O3—C18—C19108.1 (3)
C6—C7—C8121.0 (3)N—C19—C18112.2 (3)
C1—C7—C8121.2 (3)N—C20—C21i112.2 (3)
C7—C8—C9114.4 (3)O4—C21—C20i106.7 (3)
C10—C9—C15117.6 (3)O4—C22—C23111.3 (3)
C10—C9—C8120.4 (3)O1—C23—C22109.3 (3)
C23—O1—C1—C278.6 (4)C12—C13—C14—C14i0 (68)
C23—O1—C1—C7103.6 (3)C15—C13—C14—C14i0 (67)
O1—C1—C2—C4178.0 (3)C12—C13—C14—C13i119.5 (3)
C7—C1—C2—C44.3 (5)C15—C13—C14—C13i60.8 (2)
O1—C1—C2—C33.9 (4)C14i—C13—C14—C13i0 (100)
C7—C1—C2—C3173.7 (3)C16—O2—C15—C1399.0 (4)
C4—C2—C3—C2i117.0 (3)C16—O2—C15—C983.8 (4)
C1—C2—C3—C2i61.0 (3)C12—C13—C15—O2176.8 (3)
C1—C2—C4—C51.6 (5)C14i—C13—C15—O22.8 (4)
C3—C2—C4—C5176.5 (3)C14—C13—C15—O22.8 (4)
C2—C4—C5—C61.8 (6)C12—C13—C15—C96.0 (5)
C4—C5—C6—C72.6 (6)C14i—C13—C15—C9174.4 (3)
C5—C6—C7—C10.1 (5)C14—C13—C15—C9174.4 (3)
C5—C6—C7—C8178.6 (3)C10—C9—C15—O2177.4 (3)
O1—C1—C7—C6178.7 (3)C8—C9—C15—O23.5 (5)
C2—C1—C7—C63.6 (5)C10—C9—C15—C135.4 (5)
O1—C1—C7—C82.6 (4)C8—C9—C15—C13173.7 (3)
C2—C1—C7—C8175.1 (3)C15—O2—C16—C17162.5 (3)
C6—C7—C8—C9115.6 (4)C18—O3—C17—C16178.0 (3)
C1—C7—C8—C963.0 (4)O2—C16—C17—O358.5 (5)
C7—C8—C9—C10119.4 (4)C17—O3—C18—C19172.5 (3)
C7—C8—C9—C1559.6 (4)C20—N—C19—C18176.4 (3)
C15—C9—C10—C111.4 (5)O3—C18—C19—N76.2 (4)
C8—C9—C10—C11177.7 (3)C19—N—C20—C21i175.6 (3)
C9—C10—C11—C121.9 (6)C22—O4—C21—C20i170.2 (3)
C10—C11—C12—C131.3 (6)C21—O4—C22—C23177.3 (3)
C11—C12—C13—C152.5 (5)C1—O1—C23—C22165.1 (3)
C11—C12—C13—C14i177.8 (3)O4—C22—C23—O159.9 (4)
C11—C12—C13—C14177.8 (3)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW1—H1W1···N0.861.992.842 (4)168
OW1—H2W1···OW20.872.492.771 (4)100
OW2—H1W2···OW10.861.922.771 (4)167
OW2—H2W2···OW2ii0.872.162.788 (7)129
Symmetry code: (ii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC44H54N2O8·4H2O
Mr810.96
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)288
a, b, c (Å)15.922 (2), 16.7908 (16), 16.453 (4)
V3)4398.6 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.73 × 0.59 × 0.59
Data collection
DiffractometerEnraf Nonius CAD4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4330, 3861, 2185
Rint0.000
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.205, 0.99
No. of reflections3861
No. of parameters263
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.55, 0.26

Computer programs: CAD-4 EXPRESS (Enraf Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Johnson, 1976), WinGX publication routines (Farrugia, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW1—H1W1···N0.861.992.842 (4)168
OW1—H2W1···OW20.872.492.771 (4)100
OW2—H1W2···OW10.861.922.771 (4)167
OW2—H2W2···OW2i0.872.162.788 (7)129
Symmetry code: (i) x+2, y, z+1.
 

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