Melting points were determined in on Fisher-Jones melting point apparatus and are uncorrected. IR absorption spectra were recorded in the 4000 - 400 cm⁻¹ range as KBr pellets on a Perkin Elmer 283-B spectrophotometer. ¹H and ¹³C NMR spectra were recorded in CDCl₃ and DMSO-d₆ on a Unity Varian 300 MHz or 500 MHz spectrometer using TMS as an internal reference.

2-(Naphthalen-2-ylmethyl)-2,3-dihydro-1H-indene-1,2-diol (1)

In a 100 mL of a round-bottom flask, 0.5 mmol of recrystallized 3'-(naphthalen-2-yl)spiro[indene-2,2'-oxi- ran]-1(3H)-one was suspended in 50 mL of distilled ethyl ether at 0˚C with magnetic stirring. Then, 2 mmol of LiAlH₄ suspended in 10 mL of ether were added and the mixture was allowed to react for 3 h, followed by SiO₂ TLC. After acidification with 10% HCl, the extraction and evaporation of the organic solvent, a crystalline solid mp = 176˚C was obtained which was recrystallized from ethyl acetate: Hexane and 86% yield. ¹H NMR (300 MHz CDCl₃ -DMSO): δ 2.54 (d,1H, J 15.6Hz,CH₂) 3.01 (d,1H,J 15.9Hz, CH₂), 3.29 (d, 1H,J 14.4 CH₂), 3.45 (d, 1H, J 14.4 CH₂), 4.22 (s, 2H, C-OH), 5.0 (s, 1H, C-H), 7.08 - 7.22 (m, 2H, C_arylH), 7.22 - 7.42 (m, 2H, C_arylH), 7.42 - 7.53 (m, 4H, C_arylH), 7.72 - 7.81 (m, 2H, C_arylH), 8.03 (d, 1H, J 6.6 Hz, C_arylH), ¹³CNMR (¹³C{1H} 75.5 MHz, CDCl₃-DMSO): δ 34.5 (C-H), 40.9 (C-H), 82.5 ( (C-H), (C-OH)), 84.5 (C-OH), 124.1 (C_arylH), 124.3 (C_arylH), 124.6 (C_arylH), 124.7 (C_arylH), 124.7 (C_arylH), 124.8 (C_arylH), 126.0, (C_arylH), 126.0 (C_arylH), 127.3 (C_arylH), 127.8 (C_arylH), 128.5 (C_arylH), 132.2 (C_aryl), 133.1 (C_aryl), 133.2 (C_aryl), 140.1 (C_aryl), 143.9 (C_aryl), IR (1122.86 cm⁻¹ , 1596.43 cm⁻¹, 1927.62 cm⁻¹, 2873.83 cm⁻¹, 3058.53 cm⁻¹, 3283.09 cm⁻¹), EM: M+ 290 (calc. exact mass 290.36) (Scheme 1).

Scheme 1. The preparation of compound 1.

1-(3,4-Dimethoxyphenyl)-3-methoxy-3-(4-nitrophenyl)propane-1,2-diol carbon tetra chloride (2)

In a 100 mL of a round-bottom flask, 0.5 mmol of recrystallized 1-(3,4-dimethoxyphenyl)-2-hydroxy-3-me- thoxy-3-(4-nitrophenyl)propan-1-one was suspended in 50 mL of distilled THF at 0˚C with magnetic stirring. Then, 0.25 mmol of NaBH₄ suspended in 10 mL of THF were added and the mixture allowed reacting for 30 mins, followed by SiO₂ TLC. After acidification with 10% HCl and the extraction and evaporation of the organic solvent, a crystalline solid mp = 124.5˚C was obtained which was recrystallized from chloroform: hexane with 95% yield. ¹H NMR (300 MHz CDCl₃): δ 1.762 (s, 1H, C-OH), 3.015 (s, 1H, C-OH), 3.279 (s, 3H, CH₃), 3.884 (s, 3H, CH₃), 3.896 (s, 3H, CH₃), 3.913 (d, 1H, J 7.5 Hz, C-H), 4.294 (d, 1H, J 6.9 Hz, C-H), 4.572 (d, 1H, J 7.2 Hz, C-H), 6.926 (m, 3H, C_arylH), 7.599 (d, 2H, J 8.7 C_arylH), 8.223 (d, 2H, J 8.7 C_arylH), ¹³CNMR (¹³C{1H} 75.5 MHz, CDCl₃): δ 55.862 (CH₃), 55.906 (CH₃), 57.071 (CH₃), 75.631 (C-OH), 76.403 (C-OCH₃), 84.677 (C-OH), 110.185 (C_arylH), 110.987 (C_arylH), 119.873 (C_arylH), 123.384 (C_arylH), 128.512 (C_arylH), 128.890 (C_aryl), 132.459 (C_aryl), 146.007 (C_aryl), 147.843 (C_aryl), 149.140 (C_aryl), IR: (1262.64 cm⁻¹, 1346.99 cm⁻¹, 1518.96 cm⁻¹, 2934.76 cm⁻¹, 3474.43 cm⁻¹), EM:M+ 363 (calc. exact mass. 363.13) (Scheme 2).

Scheme 2. The preparation of compound 2.

Both X-ray data were collected on a Bruker Smart APEX AXS CCD area detector with a graphite monochromator and Mo Kα radiation (λ = 0.71073 Å) at room temperature by the ω scan mode. All collected data were reduced using SAINT [8] and the empirical absorption corrections were performed using SADABS program [8] . The details were shown in Table 1.

All reflections were defined based on F². 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.

All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Both structures were solved by direct methods [9] , and then refined by full-matrix least-squares technique; the position and anisotropic parameters of all the non-hydrogen atoms were obtained.

For compound 1, the Flack [10] absolute structure parameter = 0.3 (2) and its absolute configuration is inferred from the known stereochemistry of 3'-(naphthalen-2-yl)spiro[indene-2,2'-oxiran]-1(3H)-one compound deduced from chemical studies. All relevant tables and figures are based on this configuration. Table 2 showed some crystal and refinement parameters. Atomic coordinates and displacement parameters of both compounds were shown in Table 3 and Table 4, these data the structures were gained, which was shown in Figure 1. This figure was drawn with 50% displacement ellipsoids using ORTEP-3 for Windows [11] . The geometry of the molecule was calculated using the WinGX [12] and PARST [13] [14] software’s.

In both structures, the bond distances and bond angles are in good agreement with the corresponding values are within normal ranges. For molecule 1, both hydroxyl groups adopt an anti conformation with a torsion angle O1-C1-C2-O2 value of 93.1 (2)˚ [in molecule 2, both hydroxyl groups adopt a trans conformation with a torsion angle O1-C1-C2-O2 value of −171.0 (2)˚]. In structures 1 the angle and torsion angles that define the central C atom that connects to external naphthalene and indene rings C2-C10-C11, C1-C2-C10-C1 and C2-C10-C11-C12

are 114.2 (2), −173.9 (2) and −78.9 (3)˚ [in molecule 2, the angle and the torsion angles that define the central C atoms that connects to external phenyl rings C1-C2-C3, C4-C1-C2-C3, C1-C2-C3-C12 are 114.3 (2), −172.5 (2) and −66.7 (2)˚)] respectively. It is apparently that the angle and torsion angle that define the central carbon atoms are similar independently of the side groups involved.

In structure 1, the chiral centers at the C1 and C2 atoms are in the S configuration. The mean planes C1-C9, C11-C20; and C1/C4-C9, C3/C12-C17for structures 1 and 2 make dihedral angles of 28.10 (5), 89.72 (6)˚, respectively. In structure 2, the nitro group attached to the C12-C15 phenyl ring is only 6.3 (1)˚ out of the plane, the torsion angles for O6-N1-C15-C14 and O7-N1-C15-C16 are −0.9 (4) and −0.1 (4)˚, respectively. The methoxy group at C3 adopts an intermediate conformation between eclipsed and gauche conformations with respect to the C3/C12-C17 ring, the torsion angle is 33.0 (3)˚. The methoxy groups attached at C6 and C7 lie almost in the plane of the benzene ring to which they are attached C4-C9, the torsion angles C10-O4-C6-C5 and C11-O5-C7-C8 are 2.2 (3) and 8.2 (4)˚, respectively.

In structure 1, the distances between the Cg gravity centers of naphthalene and indene; between naphthalene symmetry related molecules; and between indene symmetry related rings are 5.20; 5.22 and 4.99 Å, respectively. The distance between the Cg gravity center of the ring C4-C9 and the H3B of a symmetry related molecule is 2.79 Å.

In structure 2, the distances between the Cg gravity centers of phenyl C4-C9 rings; phenyl rings C4-C9 and C12-C17; phenyl ring C4-C9 and H18B of the methoxy group at C3; and phenyl ring C12-C17 and H18C of the

methoxy group at C3 are 3.93, 6.68 3.11, and 3.25 Å, respectively.

The crystal packing in both structures 1 and 2 are dominated by O-H・・・O hydrogen bonding interactions, with donor-acceptor distances of 2.705 (2) and 2.765 (2) Å; 2.958 (3) and 2.730 (2) Å. In structure 1, these hydrogen bond interactions generate (9) ring motifs [15] . In molecule 1, each molecule is connected to two of its neighbors via intermolecular hydrogen bonds; the packing is viewed down the c-axis (Figure 2). The structure is further linked by C-H・・・π stacking interactions.

In structure 2 each molecule is connected to one of its neighbors via intermolecular hydrogen bonds, to form a two dimensional supramolecular structure along with the bc crystallographic plane (Figure 3). These hydrogen bond interactions generate two (14) and (10) ring motifs [14] . The structure is linked by C-H・・・π stacking and three C-H・・・Cl interactions forming a 3D polymer, the C-H・・・π, distances and angles for Cg gravity centers to C4-C9 and C12-C17 phenyl rings are given in Figure 4. For geometrical details and notations of all of these hydrogen bonds and intermolecular interactions are given in Table 5.