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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052853/bq2040sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052853/bq2040Isup2.hkl |
CCDC reference: 667476
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.157
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.17 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 4 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 background, see: Allen et al. (1987); Jones et al. (1979); Larson & Pecoraro (1991); Santos et al. (2001).
An anhydrous acetonitrile solution (50 ml) of 4-hydroxy-3-methoxybenzaldehyde (1.52 g, 10 mmol) was added dropwise to a solution (100 ml) of 1-(bromomethyl)-4-chlorobenzene (2.05 g, 10 mmol) and potassium carbonate (1.38 g, 10 mmol) in acetonitrile, in 30 min., and the mixture refluxed for 48 h under nitrogen atmosphere. The solvent was removed and the resultant mixture poured into ice-water (100 ml). The white precipitate was then isolated and recrystallized from acetonitrile, and then dried in a vacuum to give the pure compound in 65% yield. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.
The H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H and N—H bond lengths and isotropic U parameters: 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2—H; 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene C—H; 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl C—H.
There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). Consequently, a significant effort has been devoted to the synthesis of new Schiff base derivatives (Santos et al., 2001).
As a part of our interest in the coordination properties of Schiff bases functioning as ligands, we investigated the title compound, (I), used as a precursor in the preparation of Schiff bases.
In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The vanillin group (C1—C6/C8/O1/O2) is essentially planar, with an r.m.s. deviation for fitted atoms of 0.0090 Å. This group makes a dihedral angle of 72.79 (9)° with the benzene ring (C10—C15).
The crystal structure is stabilized by weak non-classical intermolecular C14—H14···O2 hydrogen bonds that forms centrosymmetric dimers (Table 1, Fig. 2).
For general background, see: Allen et al. (1987); Jones et al. (1979); Larson & Pecoraro (1991); Santos et al. (2001).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
![]() | Fig. 1. The structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level. |
![]() | Fig. 2. Intermolecular hydrogen bonding interactions (dashed lines). |
C15H13ClO3 | F(000) = 576 |
Mr = 276.70 | Dx = 1.334 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1181 reflections |
a = 9.054 (3) Å | θ = 2.3–21.1° |
b = 8.535 (2) Å | µ = 0.28 mm−1 |
c = 17.828 (5) Å | T = 294 K |
β = 90.10 (2)° | Block, colorless |
V = 1377.7 (7) Å3 | 0.28 × 0.22 × 0.20 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2383 independent reflections |
Radiation source: fine-focus sealed tube | 1124 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→10 |
Tmin = 0.912, Tmax = 0.946 | k = −10→10 |
6675 measured reflections | l = −20→21 |
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) = 0.157 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.064P)2 + 0.0805P] where P = (Fo2 + 2Fc2)/3 |
2383 reflections | (Δ/σ)max = 0.001 |
173 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C15H13ClO3 | V = 1377.7 (7) Å3 |
Mr = 276.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.054 (3) Å | µ = 0.28 mm−1 |
b = 8.535 (2) Å | T = 294 K |
c = 17.828 (5) Å | 0.28 × 0.22 × 0.20 mm |
β = 90.10 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 2383 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1124 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.946 | Rint = 0.048 |
6675 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.38 e Å−3 |
2383 reflections | Δρmin = −0.39 e Å−3 |
173 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 > 2σ(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 | ||
Cl1 | 0.59471 (15) | −0.34118 (12) | 0.00262 (10) | 0.1423 (8) | |
O1 | 0.9350 (2) | 0.3047 (2) | 0.11555 (14) | 0.0664 (8) | |
O2 | 1.1901 (2) | 0.2923 (2) | 0.17769 (15) | 0.0688 (8) | |
O3 | 1.3242 (3) | 0.8721 (3) | 0.23371 (18) | 0.0879 (10) | |
C1 | 0.9921 (3) | 0.4453 (4) | 0.13587 (19) | 0.0542 (9) | |
C2 | 1.1324 (4) | 0.4386 (4) | 0.17014 (19) | 0.0539 (9) | |
C3 | 1.1999 (4) | 0.5747 (4) | 0.1921 (2) | 0.0593 (10) | |
H3 | 1.2936 | 0.5707 | 0.2135 | 0.071* | |
C4 | 1.1305 (4) | 0.7187 (4) | 0.1830 (2) | 0.0560 (10) | |
C5 | 0.9929 (4) | 0.7241 (4) | 0.1508 (2) | 0.0648 (11) | |
H5 | 0.9454 | 0.8200 | 0.1454 | 0.078* | |
C6 | 0.9239 (4) | 0.5888 (4) | 0.1265 (2) | 0.0672 (11) | |
H6 | 0.8315 | 0.5943 | 0.1038 | 0.081* | |
C7 | 1.3303 (4) | 0.2813 (4) | 0.2140 (3) | 0.0829 (13) | |
H7A | 1.4013 | 0.3429 | 0.1870 | 0.124* | |
H7B | 1.3616 | 0.1739 | 0.2149 | 0.124* | |
H7C | 1.3223 | 0.3198 | 0.2644 | 0.124* | |
C8 | 1.2026 (5) | 0.8637 (4) | 0.2065 (2) | 0.0670 (11) | |
H8 | 1.1506 | 0.9567 | 0.2001 | 0.080* | |
C9 | 0.7940 (4) | 0.3070 (4) | 0.0790 (2) | 0.0767 (12) | |
H9A | 0.8002 | 0.3664 | 0.0328 | 0.092* | |
H9B | 0.7215 | 0.3566 | 0.1112 | 0.092* | |
C10 | 0.7489 (4) | 0.1425 (4) | 0.0626 (2) | 0.0554 (10) | |
C11 | 0.6410 (4) | 0.0703 (5) | 0.1033 (2) | 0.0744 (11) | |
H11 | 0.5989 | 0.1227 | 0.1437 | 0.089* | |
C12 | 0.5926 (4) | −0.0802 (6) | 0.0857 (3) | 0.0843 (14) | |
H12 | 0.5184 | −0.1286 | 0.1133 | 0.101* | |
C13 | 0.6582 (6) | −0.1550 (4) | 0.0260 (3) | 0.0778 (14) | |
C14 | 0.7666 (5) | −0.0873 (5) | −0.0142 (3) | 0.0786 (12) | |
H14 | 0.8106 | −0.1407 | −0.0537 | 0.094* | |
C15 | 0.8108 (4) | 0.0606 (4) | 0.0039 (2) | 0.0665 (10) | |
H15 | 0.8850 | 0.1077 | −0.0242 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1369 (12) | 0.0565 (7) | 0.2331 (18) | −0.0265 (6) | −0.1169 (11) | 0.0205 (8) |
O1 | 0.0558 (15) | 0.0491 (13) | 0.094 (2) | −0.0021 (11) | −0.0285 (13) | −0.0118 (13) |
O2 | 0.0572 (16) | 0.0501 (13) | 0.099 (2) | 0.0064 (11) | −0.0255 (14) | −0.0154 (13) |
O3 | 0.0724 (19) | 0.0621 (17) | 0.129 (3) | −0.0115 (13) | −0.0257 (18) | −0.0126 (15) |
C1 | 0.050 (2) | 0.054 (2) | 0.059 (3) | −0.0026 (16) | −0.0079 (17) | −0.0058 (18) |
C2 | 0.051 (2) | 0.049 (2) | 0.062 (3) | −0.0003 (16) | −0.0071 (17) | −0.0057 (18) |
C3 | 0.044 (2) | 0.056 (2) | 0.077 (3) | −0.0016 (17) | −0.0096 (17) | −0.008 (2) |
C4 | 0.054 (2) | 0.050 (2) | 0.064 (3) | −0.0048 (17) | −0.0062 (19) | −0.0051 (18) |
C5 | 0.070 (3) | 0.045 (2) | 0.080 (3) | 0.0047 (18) | −0.012 (2) | −0.0033 (19) |
C6 | 0.063 (2) | 0.055 (2) | 0.083 (3) | 0.0038 (18) | −0.025 (2) | −0.003 (2) |
C7 | 0.064 (3) | 0.061 (2) | 0.123 (4) | 0.0113 (19) | −0.036 (2) | −0.013 (2) |
C8 | 0.073 (3) | 0.050 (2) | 0.078 (3) | −0.0015 (19) | −0.002 (2) | −0.0049 (18) |
C9 | 0.070 (3) | 0.062 (2) | 0.097 (3) | −0.0031 (18) | −0.038 (2) | −0.002 (2) |
C10 | 0.050 (2) | 0.055 (2) | 0.061 (3) | −0.0015 (17) | −0.0189 (19) | −0.0009 (19) |
C11 | 0.064 (3) | 0.093 (3) | 0.066 (3) | 0.009 (2) | −0.009 (2) | 0.001 (2) |
C12 | 0.057 (3) | 0.096 (4) | 0.100 (4) | −0.024 (2) | −0.021 (2) | 0.046 (3) |
C13 | 0.076 (3) | 0.050 (2) | 0.107 (4) | −0.010 (2) | −0.052 (3) | 0.011 (2) |
C14 | 0.083 (3) | 0.068 (3) | 0.085 (3) | −0.004 (2) | −0.023 (2) | −0.017 (2) |
C15 | 0.061 (2) | 0.074 (3) | 0.064 (3) | −0.017 (2) | −0.0031 (19) | 0.000 (2) |
Cl1—C13 | 1.741 (4) | C7—H7B | 0.9600 |
O1—C1 | 1.355 (4) | C7—H7C | 0.9600 |
O1—C9 | 1.432 (4) | C8—H8 | 0.9300 |
O2—C2 | 1.360 (4) | C9—C10 | 1.491 (4) |
O2—C7 | 1.427 (4) | C9—H9A | 0.9700 |
O3—C8 | 1.204 (4) | C9—H9B | 0.9700 |
C1—C6 | 1.381 (4) | C10—C11 | 1.365 (5) |
C1—C2 | 1.410 (4) | C10—C15 | 1.378 (5) |
C2—C3 | 1.369 (4) | C11—C12 | 1.393 (5) |
C3—C4 | 1.390 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.376 (6) |
C4—C5 | 1.371 (5) | C12—H12 | 0.9300 |
C4—C8 | 1.461 (4) | C13—C14 | 1.347 (6) |
C5—C6 | 1.383 (4) | C14—C15 | 1.363 (5) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—H7A | 0.9600 | ||
C1—O1—C9 | 116.7 (2) | O3—C8—H8 | 117.5 |
C2—O2—C7 | 116.5 (2) | C4—C8—H8 | 117.5 |
O1—C1—C6 | 125.6 (3) | O1—C9—C10 | 108.7 (3) |
O1—C1—C2 | 115.0 (3) | O1—C9—H9A | 110.0 |
C6—C1—C2 | 119.4 (3) | C10—C9—H9A | 110.0 |
O2—C2—C3 | 125.4 (3) | O1—C9—H9B | 110.0 |
O2—C2—C1 | 115.2 (3) | C10—C9—H9B | 110.0 |
C3—C2—C1 | 119.4 (3) | H9A—C9—H9B | 108.3 |
C2—C3—C4 | 121.0 (3) | C11—C10—C15 | 117.9 (3) |
C2—C3—H3 | 119.5 | C11—C10—C9 | 121.1 (4) |
C4—C3—H3 | 119.5 | C15—C10—C9 | 121.0 (4) |
C5—C4—C3 | 119.3 (3) | C10—C11—C12 | 121.4 (4) |
C5—C4—C8 | 119.8 (3) | C10—C11—H11 | 119.3 |
C3—C4—C8 | 120.9 (3) | C12—C11—H11 | 119.3 |
C4—C5—C6 | 120.8 (3) | C13—C12—C11 | 117.8 (4) |
C4—C5—H5 | 119.6 | C13—C12—H12 | 121.1 |
C6—C5—H5 | 119.6 | C11—C12—H12 | 121.1 |
C1—C6—C5 | 120.1 (3) | C14—C13—C12 | 121.9 (4) |
C1—C6—H6 | 120.0 | C14—C13—Cl1 | 120.3 (4) |
C5—C6—H6 | 120.0 | C12—C13—Cl1 | 117.8 (4) |
O2—C7—H7A | 109.5 | C13—C14—C15 | 119.0 (4) |
O2—C7—H7B | 109.5 | C13—C14—H14 | 120.5 |
H7A—C7—H7B | 109.5 | C15—C14—H14 | 120.5 |
O2—C7—H7C | 109.5 | C14—C15—C10 | 122.0 (4) |
H7A—C7—H7C | 109.5 | C14—C15—H15 | 119.0 |
H7B—C7—H7C | 109.5 | C10—C15—H15 | 119.0 |
O3—C8—C4 | 125.0 (3) | ||
C9—O1—C1—C6 | 2.2 (5) | C4—C5—C6—C1 | 1.4 (6) |
C9—O1—C1—C2 | −178.7 (3) | C5—C4—C8—O3 | −178.3 (4) |
C7—O2—C2—C3 | 2.3 (5) | C3—C4—C8—O3 | 1.2 (6) |
C7—O2—C2—C1 | −178.4 (3) | C1—O1—C9—C10 | −178.9 (3) |
O1—C1—C2—O2 | 0.1 (5) | O1—C9—C10—C11 | 106.1 (4) |
C6—C1—C2—O2 | 179.3 (3) | O1—C9—C10—C15 | −76.4 (4) |
O1—C1—C2—C3 | 179.5 (3) | C15—C10—C11—C12 | −1.1 (5) |
C6—C1—C2—C3 | −1.3 (5) | C9—C10—C11—C12 | 176.4 (3) |
O2—C2—C3—C4 | −179.0 (3) | C10—C11—C12—C13 | 0.6 (6) |
C1—C2—C3—C4 | 1.7 (5) | C11—C12—C13—C14 | 0.6 (6) |
C2—C3—C4—C5 | −0.6 (5) | C11—C12—C13—Cl1 | −178.5 (3) |
C2—C3—C4—C8 | 179.9 (4) | C12—C13—C14—C15 | −1.2 (6) |
C3—C4—C5—C6 | −1.0 (6) | Cl1—C13—C14—C15 | 177.9 (3) |
C8—C4—C5—C6 | 178.5 (3) | C13—C14—C15—C10 | 0.6 (6) |
O1—C1—C6—C5 | 178.9 (3) | C11—C10—C15—C14 | 0.5 (5) |
C2—C1—C6—C5 | −0.3 (6) | C9—C10—C15—C14 | −177.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O2i | 0.93 | 2.56 | 3.423 (5) | 154 |
Symmetry code: (i) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H13ClO3 |
Mr | 276.70 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 9.054 (3), 8.535 (2), 17.828 (5) |
β (°) | 90.10 (2) |
V (Å3) | 1377.7 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.28 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.912, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6675, 2383, 1124 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.157, 1.08 |
No. of reflections | 2383 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.39 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O2i | 0.93 | 2.56 | 3.423 (5) | 154 |
Symmetry code: (i) −x+2, −y, −z. |
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There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). Consequently, a significant effort has been devoted to the synthesis of new Schiff base derivatives (Santos et al., 2001).
As a part of our interest in the coordination properties of Schiff bases functioning as ligands, we investigated the title compound, (I), used as a precursor in the preparation of Schiff bases.
In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The vanillin group (C1—C6/C8/O1/O2) is essentially planar, with an r.m.s. deviation for fitted atoms of 0.0090 Å. This group makes a dihedral angle of 72.79 (9)° with the benzene ring (C10—C15).
The crystal structure is stabilized by weak non-classical intermolecular C14—H14···O2 hydrogen bonds that forms centrosymmetric dimers (Table 1, Fig. 2).