Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018181/hk2231sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018181/hk2231Isup2.hkl |
CCDC reference: 647574
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.139
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 1368 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1537 Completeness (_total/calc) 89.00% PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.89
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.22
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general backgroud, see: Allen et al. (1987); Du et al. (2002); Dugas & Penney, 1981; Easmon et al. (2001); Finch et al. (1999); Greenbaum et al. (2004); Jones et al. (1979); Sancak et al. (2007); Sengottuvelan et al. (2002); Vigato & Tamburini (2004); Wilson et al. (1974). For a related structure see: Ustabaş et al. (2006). For structure analysis tools used, see: Bruker (1997); Farrugia (1997); Farrugia (1999); Sheldrick (1997).
For the preparation of the title compound, the corresponding 4-hydroxy-3-methoxy benzaldehyde (3.04 g, 10 mmol) was refluxed with potassium hydroxide (1.121 g, 10 mmol) in absolute ethanol (100 ml) for 1 h. Then, trans 1,4-dichloro2-butene (2.138 g, 40 mmol) was added and refluxed for an additional 26 h. The precipitate was filtered off, washed with water and recrystallized from chloroform/acetone (1:1) (yield; 2.145 g, 60%, m.p. 444–445 K).
H10 was located in difference syntheses and refined isotropically [C—H = 0.90 (3) Å and Uiso(H) = 0.056 (9) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Benzaldehyde and its derivatives are the major important compounds to obtain biologically active compounds. The aldehyde (thio)semicarbazones are a class of small molecules that have been evaluated over the last 50 years as antiviral, anticancer (Finch et al., 1999) and antiparasitical (Greenbaum et al., 2004; Wilson et al., 1974; Du et al., 2002; Easmon et al., 2001). Benzaldehyde derivatives are important starting materials for obtaining Schiff bases and oxime-type ligands and their transition metal complexes (Vigato & Tamburini, 2004; Sancak et al., 2007). These types of ligands display a wide variety of structures with different flexibility and electronic nature and the presence of additional donor atoms besides imino nitrogen. Further finetuning of their coordination characteristics can be achieved by varying the nature and positions of the substituents. Some Schiff bases and their complexes have been studied because of catalytic activities in hydrogenation of olefins (Jones et al., 1979) and photochromic properties (Dugas & Pennev, 1981). Many reports have demonstrated the potential of Schiff base or oxime complexes in the construction of polynuclear aromatic compounds (Sengottuvelan et al., 2002).
In the molecule of (I), (Fig. 1), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). It has a centre of symmetry located at the mid-point of the C═C double bond. The atoms C7, O1, O2 and O3 lie in the benzene ring plane, while atoms C8, C9 and C10 are 0.134 (3), 0.089 (2) and 0.142 (3) Å away, respectively. The O3═C7 bond [1.210 (4) Å] agrees with the corresponding value [1.200 (3) Å] in 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis- (naphthalene-1-carbaldehyde) (Ustabaş et al., 2006).
For general backgroud, see: Allen et al. (1987); Du et al. (2002); Dugas & Penney, 1981; Easmon et al. (2001); Finch et al. (1999); Greenbaum et al. (2004); Jones et al. (1979); Sancak et al. (2007); Sengottuvelan et al. (2002); Vigato & Tamburini (2004); Wilson et al. (1974). For a related structure see: Ustabaş et al. (2006). For structure analysis tools used, see: Bruker (1997); Farrugia (1997); Farrugia (1999); Sheldrick (1997).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C20H20O6 | F(000) = 376 |
Mr = 356.36 | Dx = 1.359 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 836 reflections |
a = 4.0639 (9) Å | θ = 2.0–25.0° |
b = 15.617 (3) Å | µ = 0.10 mm−1 |
c = 13.735 (3) Å | T = 294 K |
β = 92.212 (4)° | Prism, colorless |
V = 871.0 (3) Å3 | 0.42 × 0.19 × 0.16 mm |
Z = 2 |
Bruker CCD area-detector diffractometer | 836 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
φ and ω scans | h = −4→4 |
3568 measured reflections | k = −18→13 |
1368 independent reflections | l = −16→13 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3 |
1368 reflections | (Δ/σ)max < 0.001 |
122 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C20H20O6 | V = 871.0 (3) Å3 |
Mr = 356.36 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.0639 (9) Å | µ = 0.10 mm−1 |
b = 15.617 (3) Å | T = 294 K |
c = 13.735 (3) Å | 0.42 × 0.19 × 0.16 mm |
β = 92.212 (4)° |
Bruker CCD area-detector diffractometer | 836 reflections with I > 2σ(I) |
3568 measured reflections | Rint = 0.046 |
1368 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.16 e Å−3 |
1368 reflections | Δρmin = −0.18 e Å−3 |
122 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.2583 (5) | 0.83308 (11) | 0.95737 (14) | 0.0456 (6) | |
O2 | 1.4321 (5) | 0.69144 (11) | 1.03941 (14) | 0.0528 (6) | |
O3 | 1.9445 (7) | 0.51354 (15) | 0.76387 (18) | 0.0788 (9) | |
C1 | 1.3981 (7) | 0.77503 (15) | 0.8979 (2) | 0.0368 (7) | |
C2 | 1.4979 (7) | 0.69800 (15) | 0.9429 (2) | 0.0382 (7) | |
C3 | 1.6459 (7) | 0.63623 (16) | 0.8898 (2) | 0.0432 (8) | |
H3 | 1.7129 | 0.5853 | 0.9197 | 0.052* | |
C4 | 1.6976 (7) | 0.64900 (16) | 0.7908 (2) | 0.0418 (8) | |
C5 | 1.6001 (8) | 0.72447 (18) | 0.7472 (2) | 0.0490 (8) | |
H5 | 1.6336 | 0.7330 | 0.6813 | 0.059* | |
C6 | 1.4525 (7) | 0.78787 (17) | 0.8007 (2) | 0.0447 (8) | |
H6 | 1.3901 | 0.8392 | 0.7710 | 0.054* | |
C7 | 1.8599 (8) | 0.5833 (2) | 0.7339 (3) | 0.0585 (10) | |
H7 | 1.9016 | 0.5963 | 0.6695 | 0.070* | |
C8 | 1.5004 (10) | 0.61245 (19) | 1.0854 (3) | 0.0714 (12) | |
H8A | 1.4426 | 0.6156 | 1.1524 | 0.107* | |
H8B | 1.7309 | 0.5998 | 1.0819 | 0.107* | |
H8C | 1.3743 | 0.5681 | 1.0531 | 0.107* | |
C9 | 1.1295 (8) | 0.91024 (15) | 0.9134 (2) | 0.0440 (8) | |
H9A | 0.9700 | 0.8965 | 0.8614 | 0.053* | |
H9B | 1.3059 | 0.9434 | 0.8862 | 0.053* | |
C10 | 0.9710 (7) | 0.95961 (17) | 0.9906 (2) | 0.0401 (8) | |
H10 | 0.830 (7) | 0.9284 (18) | 1.025 (2) | 0.056 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0663 (15) | 0.0312 (11) | 0.0405 (14) | 0.0094 (9) | 0.0170 (10) | 0.0012 (9) |
O2 | 0.0896 (16) | 0.0399 (11) | 0.0303 (13) | 0.0138 (11) | 0.0198 (11) | 0.0025 (9) |
O3 | 0.102 (2) | 0.0513 (15) | 0.085 (2) | 0.0161 (14) | 0.0317 (17) | −0.0153 (13) |
C1 | 0.0444 (18) | 0.0317 (15) | 0.0352 (19) | −0.0031 (12) | 0.0125 (14) | −0.0046 (12) |
C2 | 0.0543 (19) | 0.0326 (15) | 0.0283 (18) | 0.0017 (13) | 0.0102 (14) | −0.0015 (12) |
C3 | 0.059 (2) | 0.0293 (15) | 0.042 (2) | −0.0005 (13) | 0.0147 (15) | −0.0020 (13) |
C4 | 0.051 (2) | 0.0380 (17) | 0.0371 (19) | −0.0078 (13) | 0.0144 (15) | −0.0104 (13) |
C5 | 0.065 (2) | 0.0490 (19) | 0.0344 (19) | −0.0097 (15) | 0.0164 (16) | −0.0047 (14) |
C6 | 0.061 (2) | 0.0362 (16) | 0.0373 (19) | 0.0002 (14) | 0.0138 (15) | 0.0028 (13) |
C7 | 0.074 (2) | 0.052 (2) | 0.051 (2) | −0.0059 (18) | 0.0274 (19) | −0.0176 (16) |
C8 | 0.120 (3) | 0.055 (2) | 0.041 (2) | 0.023 (2) | 0.016 (2) | 0.0109 (17) |
C9 | 0.0533 (19) | 0.0331 (15) | 0.046 (2) | 0.0032 (13) | 0.0079 (15) | 0.0017 (13) |
C10 | 0.0435 (19) | 0.0335 (14) | 0.044 (2) | −0.0011 (14) | 0.0118 (15) | 0.0035 (14) |
O1—C1 | 1.359 (3) | C5—H5 | 0.9300 |
O1—C9 | 1.438 (3) | C6—C5 | 1.383 (4) |
O2—C2 | 1.366 (3) | C6—H6 | 0.9300 |
O2—C8 | 1.408 (3) | C7—H7 | 0.9300 |
O3—C7 | 1.210 (4) | C8—H8A | 0.9600 |
C1—C6 | 1.376 (4) | C8—H8B | 0.9600 |
C1—C2 | 1.405 (3) | C8—H8C | 0.9600 |
C2—C3 | 1.363 (4) | C9—H9A | 0.9700 |
C3—C4 | 1.398 (4) | C9—H9B | 0.9700 |
C3—H3 | 0.9300 | C10—C10i | 1.307 (5) |
C4—C7 | 1.462 (4) | C10—C9 | 1.479 (4) |
C5—C4 | 1.373 (4) | C10—H10 | 0.90 (3) |
C1—O1—C9 | 117.4 (2) | C5—C6—H6 | 120.0 |
C2—O2—C8 | 117.3 (2) | O3—C7—C4 | 125.3 (3) |
O1—C1—C6 | 124.9 (2) | O3—C7—H7 | 117.3 |
O1—C1—C2 | 115.3 (2) | C4—C7—H7 | 117.3 |
C6—C1—C2 | 119.8 (2) | O2—C8—H8A | 109.5 |
C3—C2—O2 | 124.9 (2) | O2—C8—H8B | 109.5 |
C3—C2—C1 | 119.8 (3) | H8A—C8—H8B | 109.5 |
O2—C2—C1 | 115.3 (2) | O2—C8—H8C | 109.5 |
C2—C3—C4 | 120.3 (3) | H8A—C8—H8C | 109.5 |
C2—C3—H3 | 119.8 | H8B—C8—H8C | 109.5 |
C4—C3—H3 | 119.8 | O1—C9—C10 | 107.3 (2) |
C5—C4—C3 | 119.7 (3) | O1—C9—H9A | 110.3 |
C5—C4—C7 | 119.8 (3) | C10—C9—H9A | 110.3 |
C3—C4—C7 | 120.5 (3) | O1—C9—H9B | 110.3 |
C4—C5—C6 | 120.4 (3) | C10—C9—H9B | 110.3 |
C4—C5—H5 | 119.8 | H9A—C9—H9B | 108.5 |
C6—C5—H5 | 119.8 | C10i—C10—C9 | 124.4 (4) |
C1—C6—C5 | 120.0 (3) | C10i—C10—H10 | 122 (2) |
C1—C6—H6 | 120.0 | C9—C10—H10 | 113.5 (19) |
C9—O1—C1—C6 | 6.3 (4) | O2—C2—C3—C4 | 179.1 (3) |
C9—O1—C1—C2 | −175.4 (2) | C1—C2—C3—C4 | −0.3 (5) |
C1—O1—C9—C10 | 176.0 (2) | C2—C3—C4—C5 | 0.4 (5) |
C8—O2—C2—C3 | −5.0 (4) | C2—C3—C4—C7 | 179.2 (3) |
C8—O2—C2—C1 | 174.4 (3) | C5—C4—C7—O3 | −177.1 (3) |
O1—C1—C2—C3 | −178.9 (3) | C3—C4—C7—O3 | 4.1 (5) |
C6—C1—C2—C3 | −0.5 (4) | C6—C5—C4—C3 | 0.2 (5) |
O1—C1—C2—O2 | 1.7 (4) | C6—C5—C4—C7 | −178.6 (3) |
C6—C1—C2—O2 | −179.9 (3) | C1—C6—C5—C4 | −1.0 (5) |
O1—C1—C6—C5 | 179.3 (3) | C10i—C10—C9—O1 | 129.2 (4) |
C2—C1—C6—C5 | 1.1 (4) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H20O6 |
Mr | 356.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 4.0639 (9), 15.617 (3), 13.735 (3) |
β (°) | 92.212 (4) |
V (Å3) | 871.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.42 × 0.19 × 0.16 |
Data collection | |
Diffractometer | Bruker CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3568, 1368, 836 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.139, 1.04 |
No. of reflections | 1368 |
No. of parameters | 122 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
O1—C1 | 1.359 (3) | O2—C8 | 1.408 (3) |
O1—C9 | 1.438 (3) | O3—C7 | 1.210 (4) |
O2—C2 | 1.366 (3) | ||
C3—C2—O2 | 124.9 (2) | O2—C2—C1 | 115.3 (2) |
C3—C2—C1 | 119.8 (3) |
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Benzaldehyde and its derivatives are the major important compounds to obtain biologically active compounds. The aldehyde (thio)semicarbazones are a class of small molecules that have been evaluated over the last 50 years as antiviral, anticancer (Finch et al., 1999) and antiparasitical (Greenbaum et al., 2004; Wilson et al., 1974; Du et al., 2002; Easmon et al., 2001). Benzaldehyde derivatives are important starting materials for obtaining Schiff bases and oxime-type ligands and their transition metal complexes (Vigato & Tamburini, 2004; Sancak et al., 2007). These types of ligands display a wide variety of structures with different flexibility and electronic nature and the presence of additional donor atoms besides imino nitrogen. Further finetuning of their coordination characteristics can be achieved by varying the nature and positions of the substituents. Some Schiff bases and their complexes have been studied because of catalytic activities in hydrogenation of olefins (Jones et al., 1979) and photochromic properties (Dugas & Pennev, 1981). Many reports have demonstrated the potential of Schiff base or oxime complexes in the construction of polynuclear aromatic compounds (Sengottuvelan et al., 2002).
In the molecule of (I), (Fig. 1), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). It has a centre of symmetry located at the mid-point of the C═C double bond. The atoms C7, O1, O2 and O3 lie in the benzene ring plane, while atoms C8, C9 and C10 are 0.134 (3), 0.089 (2) and 0.142 (3) Å away, respectively. The O3═C7 bond [1.210 (4) Å] agrees with the corresponding value [1.200 (3) Å] in 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis- (naphthalene-1-carbaldehyde) (Ustabaş et al., 2006).