Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107054959/hj3056sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107054959/hj3056Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107054959/hj3056IIsup3.hkl |
CCDC references: 672560; 672561
For related literature, see: Bacelo et al. (1997); Loupy et al. (2005); Saczewski et al. (2004); Sonar et al. (2004, 2006); Wilson (1992).
The title compounds were prepared according to the previously reported procedure of Sonar et al. (2004). Recrystallization from ethyl acetate afforded yellow needles of (I), which were suitable for X-ray analysis; compound (II) was crystallized from a mixture of ethyl acetate and chloroform by slow evaporation over a period of one week affording pale-yellow crystals. For (I): 1H NMR (DMSO-d6, p.p.m.): δ 3.72 (s, 3H), 3.88 (s, 6H), 7.04 (s, 2H), 7.43–7.52 (m, 2H), 7.99 (dd, 1H), 8.03 (s, 1H), 8.09 (dd, 1H), 8.40 (s, 1H); 13C NMR (DMSO-d6, p.p.m.): δ 56.12, 60.18, 103.25, 108.75, 117.66, 122.67, 124.69, 125.18, 126.70, 128.67, 131.48, 135.52, 137.30, 138.01, 138.42, 140.17, 153.11. For (II): 1H NMR (DMSO-d6, p.p.m.): δ 3.76 (s, 3H), 3.85 (s, 3H), 7.02–7.13 (m, 3H), 7.33–7.39 (sextet, 2H), 7.82–7.89 (m, 3H), 8.01 (s, 1H); 13C NMR (DMSO-d6, p.p.m.): δ 55.53, 55.62, 110.87, 112.16, 119.97, 121.84, 122.31, 123.43, 124.48, 124.86, 126.52, 132.27, 136.55, 137.28, 138.01, 140.85, 149.02, 150.00.
H atoms were found in difference Fourier maps and subsequently placed in idealized positions, with constrained C—H distances of 0.98 Å for methyl H atoms and 0.95 Å for all other H atoms. Uiso(H) values were set to either 1.5Ueq of the attached C atom (CHMe) or 1.2Ueq.
For both compounds, data collection: COLLECT (Nonius, 1999). Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for (I); SCALEPACK (Otwinowski & Minor, 1997) for (II). For both compounds, data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and local procedures for (I); SHELX97-2 (Sheldrick, 1997) and local procedures for (II).
C20H17NO3S | F(000) = 736 |
Mr = 351.41 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4000 reflections |
a = 7.4136 (1) Å | θ = 1.0–27.5° |
b = 23.4782 (3) Å | µ = 0.21 mm−1 |
c = 10.3932 (2) Å | T = 90 K |
β = 110.3689 (6)° | Block, yellow |
V = 1695.90 (5) Å3 | 0.40 × 0.15 × 0.15 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3894 independent reflections |
Radiation source: fine-focus sealed tube | 2800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans at fixed χ = 55° | h = −9→9 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −30→30 |
Tmin = 0.921, Tmax = 0.969 | l = −13→13 |
7649 measured reflections |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0734P)2] where P = (Fo2 + 2Fc2)/3 |
3894 reflections | (Δ/σ)max = 0.001 |
229 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C20H17NO3S | V = 1695.90 (5) Å3 |
Mr = 351.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4136 (1) Å | µ = 0.21 mm−1 |
b = 23.4782 (3) Å | T = 90 K |
c = 10.3932 (2) Å | 0.40 × 0.15 × 0.15 mm |
β = 110.3689 (6)° |
Nonius KappaCCD diffractometer | 3894 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 2800 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.969 | Rint = 0.037 |
7649 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.65 e Å−3 |
3894 reflections | Δρmin = −0.29 e Å−3 |
229 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 | ||
C1 | 0.3938 (3) | 0.10313 (7) | 0.69464 (18) | 0.0174 (4) | |
C2 | 0.2318 (3) | 0.12391 (8) | 0.59714 (18) | 0.0190 (4) | |
H2 | 0.2314 | 0.1565 | 0.5428 | 0.023* | |
C3 | 0.0630 (3) | 0.09190 (8) | 0.58485 (18) | 0.0174 (4) | |
C4 | −0.1279 (3) | 0.10123 (8) | 0.49813 (18) | 0.0194 (4) | |
H4 | −0.1589 | 0.1326 | 0.4364 | 0.023* | |
C5 | −0.2693 (3) | 0.06441 (8) | 0.50385 (18) | 0.0216 (4) | |
H5 | −0.3987 | 0.0706 | 0.4458 | 0.026* | |
C6 | −0.2255 (3) | 0.01792 (8) | 0.59391 (18) | 0.0223 (4) | |
H6 | −0.3254 | −0.0071 | 0.5954 | 0.027* | |
C7 | −0.0398 (3) | 0.00793 (8) | 0.68028 (18) | 0.0201 (4) | |
H7 | −0.0107 | −0.0235 | 0.7416 | 0.024* | |
C8 | 0.1047 (3) | 0.04518 (8) | 0.67566 (18) | 0.0167 (4) | |
C9 | 0.5784 (3) | 0.13082 (8) | 0.72847 (18) | 0.0177 (4) | |
H9 | 0.5799 | 0.1627 | 0.6727 | 0.021* | |
C10 | 0.7512 (3) | 0.11865 (7) | 0.82757 (18) | 0.0171 (4) | |
C11 | 0.9257 (2) | 0.15426 (7) | 0.85742 (17) | 0.0167 (4) | |
C12 | 0.9141 (3) | 0.20886 (8) | 0.80229 (18) | 0.0169 (4) | |
H12 | 0.7959 | 0.2223 | 0.7386 | 0.020* | |
C13 | 1.0761 (2) | 0.24353 (7) | 0.84090 (18) | 0.0164 (4) | |
C14 | 1.2515 (2) | 0.22414 (7) | 0.93442 (18) | 0.0169 (4) | |
C15 | 1.2635 (3) | 0.16874 (8) | 0.98500 (18) | 0.0171 (4) | |
C16 | 1.1015 (3) | 0.13394 (8) | 0.94715 (18) | 0.0165 (4) | |
H16 | 1.1105 | 0.0963 | 0.9824 | 0.020* | |
C17 | 0.7683 (2) | 0.07009 (8) | 0.91516 (18) | 0.0182 (4) | |
C18 | 0.9084 (3) | 0.31770 (8) | 0.68987 (19) | 0.0239 (4) | |
H18A | 0.8857 | 0.2941 | 0.6080 | 0.036* | |
H18B | 0.9254 | 0.3575 | 0.6678 | 0.036* | |
H18C | 0.7978 | 0.3148 | 0.7206 | 0.036* | |
C19 | 1.5106 (3) | 0.26532 (10) | 0.8875 (2) | 0.0336 (5) | |
H19A | 1.5640 | 0.2282 | 0.8764 | 0.050* | |
H19B | 1.6154 | 0.2928 | 0.9242 | 0.050* | |
H19C | 1.4228 | 0.2786 | 0.7983 | 0.050* | |
C20 | 1.4546 (3) | 0.09798 (8) | 1.13619 (18) | 0.0231 (4) | |
H20A | 1.3699 | 0.0970 | 1.1905 | 0.035* | |
H20B | 1.5877 | 0.0912 | 1.1963 | 0.035* | |
H20C | 1.4153 | 0.0683 | 1.0655 | 0.035* | |
N1 | 0.7871 (2) | 0.03196 (7) | 0.98803 (17) | 0.0270 (4) | |
O1 | 1.07742 (18) | 0.29845 (5) | 0.79637 (13) | 0.0203 (3) | |
O2 | 1.40808 (17) | 0.25991 (5) | 0.98027 (13) | 0.0201 (3) | |
O3 | 1.44129 (17) | 0.15257 (5) | 1.07228 (13) | 0.0204 (3) | |
S1 | 0.34697 (7) | 0.042019 (19) | 0.77452 (5) | 0.01819 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0181 (10) | 0.0164 (9) | 0.0178 (9) | −0.0015 (7) | 0.0062 (8) | −0.0005 (7) |
C2 | 0.0195 (10) | 0.0191 (10) | 0.0173 (9) | 0.0003 (8) | 0.0051 (8) | 0.0014 (8) |
C3 | 0.0172 (10) | 0.0184 (10) | 0.0160 (9) | 0.0016 (7) | 0.0048 (8) | −0.0021 (7) |
C4 | 0.0188 (10) | 0.0210 (10) | 0.0167 (9) | 0.0035 (8) | 0.0040 (8) | 0.0007 (8) |
C5 | 0.0154 (10) | 0.0290 (11) | 0.0177 (9) | 0.0009 (8) | 0.0023 (8) | −0.0028 (8) |
C6 | 0.0171 (10) | 0.0272 (11) | 0.0222 (10) | −0.0055 (8) | 0.0064 (8) | −0.0021 (8) |
C7 | 0.0210 (10) | 0.0204 (10) | 0.0170 (9) | −0.0023 (8) | 0.0042 (8) | −0.0007 (8) |
C8 | 0.0149 (9) | 0.0187 (10) | 0.0151 (9) | 0.0007 (7) | 0.0033 (7) | −0.0023 (7) |
C9 | 0.0191 (10) | 0.0169 (9) | 0.0169 (9) | −0.0024 (7) | 0.0061 (8) | −0.0002 (7) |
C10 | 0.0185 (10) | 0.0160 (9) | 0.0170 (9) | −0.0021 (7) | 0.0064 (8) | −0.0009 (7) |
C11 | 0.0170 (10) | 0.0189 (10) | 0.0147 (9) | −0.0017 (8) | 0.0060 (8) | −0.0032 (7) |
C12 | 0.0158 (9) | 0.0181 (10) | 0.0167 (9) | −0.0004 (7) | 0.0055 (8) | −0.0001 (7) |
C13 | 0.0173 (9) | 0.0147 (9) | 0.0188 (9) | 0.0006 (7) | 0.0082 (8) | −0.0008 (7) |
C14 | 0.0150 (9) | 0.0161 (9) | 0.0202 (9) | −0.0029 (7) | 0.0070 (8) | −0.0025 (7) |
C15 | 0.0153 (9) | 0.0184 (9) | 0.0159 (9) | 0.0026 (7) | 0.0032 (8) | 0.0002 (7) |
C16 | 0.0173 (10) | 0.0156 (9) | 0.0165 (9) | −0.0004 (7) | 0.0057 (8) | 0.0004 (7) |
C17 | 0.0117 (9) | 0.0215 (10) | 0.0183 (9) | −0.0023 (8) | 0.0014 (7) | −0.0006 (8) |
C18 | 0.0254 (11) | 0.0219 (10) | 0.0213 (10) | 0.0007 (8) | 0.0041 (9) | 0.0053 (8) |
C19 | 0.0300 (12) | 0.0388 (13) | 0.0395 (13) | −0.0132 (10) | 0.0215 (11) | −0.0093 (10) |
C20 | 0.0232 (11) | 0.0201 (10) | 0.0206 (10) | 0.0003 (8) | 0.0008 (9) | 0.0055 (8) |
N1 | 0.0184 (9) | 0.0294 (10) | 0.0277 (9) | −0.0029 (7) | 0.0010 (8) | 0.0091 (8) |
O1 | 0.0177 (7) | 0.0150 (7) | 0.0252 (7) | −0.0010 (5) | 0.0039 (6) | 0.0033 (5) |
O2 | 0.0183 (7) | 0.0180 (7) | 0.0237 (7) | −0.0054 (5) | 0.0072 (6) | −0.0044 (5) |
O3 | 0.0138 (7) | 0.0181 (7) | 0.0240 (7) | 0.0007 (5) | −0.0003 (6) | 0.0035 (5) |
S1 | 0.0152 (3) | 0.0175 (3) | 0.0192 (3) | −0.00158 (18) | 0.00255 (19) | 0.00203 (18) |
C1—C2 | 1.364 (2) | C12—C13 | 1.389 (2) |
C1—C9 | 1.443 (2) | C12—H12 | 0.9500 |
C1—S1 | 1.7519 (18) | C13—O1 | 1.371 (2) |
C2—C3 | 1.427 (3) | C13—C14 | 1.401 (2) |
C2—H2 | 0.9500 | C14—O2 | 1.376 (2) |
C3—C4 | 1.406 (2) | C14—C15 | 1.394 (3) |
C3—C8 | 1.409 (3) | C15—O3 | 1.368 (2) |
C4—C5 | 1.376 (3) | C15—C16 | 1.391 (2) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.401 (3) | C17—N1 | 1.149 (2) |
C5—H5 | 0.9500 | C18—O1 | 1.426 (2) |
C6—C7 | 1.377 (3) | C18—H18A | 0.9800 |
C6—H6 | 0.9500 | C18—H18B | 0.9800 |
C7—C8 | 1.397 (3) | C18—H18C | 0.9800 |
C7—H7 | 0.9500 | C19—O2 | 1.426 (2) |
C8—S1 | 1.7328 (19) | C19—H19A | 0.9800 |
C9—C10 | 1.366 (2) | C19—H19B | 0.9800 |
C9—H9 | 0.9500 | C19—H19C | 0.9800 |
C10—C17 | 1.437 (2) | C20—O3 | 1.431 (2) |
C10—C11 | 1.480 (2) | C20—H20A | 0.9800 |
C11—C12 | 1.394 (2) | C20—H20B | 0.9800 |
C11—C16 | 1.396 (2) | C20—H20C | 0.9800 |
C2—C1—C9 | 122.33 (17) | O1—C13—C12 | 124.09 (16) |
C2—C1—S1 | 112.12 (14) | O1—C13—C14 | 115.20 (15) |
C9—C1—S1 | 125.51 (14) | C12—C13—C14 | 120.68 (17) |
C1—C2—C3 | 113.33 (17) | O2—C14—C15 | 120.21 (16) |
C1—C2—H2 | 123.3 | O2—C14—C13 | 120.61 (16) |
C3—C2—H2 | 123.3 | C15—C14—C13 | 119.13 (16) |
C4—C3—C8 | 119.20 (17) | O3—C15—C16 | 124.20 (16) |
C4—C3—C2 | 129.14 (17) | O3—C15—C14 | 115.42 (15) |
C8—C3—C2 | 111.66 (16) | C16—C15—C14 | 120.38 (16) |
C5—C4—C3 | 119.12 (17) | C15—C16—C11 | 120.09 (17) |
C5—C4—H4 | 120.4 | C15—C16—H16 | 120.0 |
C3—C4—H4 | 120.4 | C11—C16—H16 | 120.0 |
C4—C5—C6 | 121.04 (17) | N1—C17—C10 | 177.9 (2) |
C4—C5—H5 | 119.5 | O1—C18—H18A | 109.5 |
C6—C5—H5 | 119.5 | O1—C18—H18B | 109.5 |
C7—C6—C5 | 121.01 (18) | H18A—C18—H18B | 109.5 |
C7—C6—H6 | 119.5 | O1—C18—H18C | 109.5 |
C5—C6—H6 | 119.5 | H18A—C18—H18C | 109.5 |
C6—C7—C8 | 118.41 (18) | H18B—C18—H18C | 109.5 |
C6—C7—H7 | 120.8 | O2—C19—H19A | 109.5 |
C8—C7—H7 | 120.8 | O2—C19—H19B | 109.5 |
C7—C8—C3 | 121.22 (17) | H19A—C19—H19B | 109.5 |
C7—C8—S1 | 127.02 (15) | O2—C19—H19C | 109.5 |
C3—C8—S1 | 111.76 (14) | H19A—C19—H19C | 109.5 |
C10—C9—C1 | 130.57 (17) | H19B—C19—H19C | 109.5 |
C10—C9—H9 | 114.7 | O3—C20—H20A | 109.5 |
C1—C9—H9 | 114.7 | O3—C20—H20B | 109.5 |
C9—C10—C17 | 119.79 (16) | H20A—C20—H20B | 109.5 |
C9—C10—C11 | 124.21 (16) | O3—C20—H20C | 109.5 |
C17—C10—C11 | 115.92 (16) | H20A—C20—H20C | 109.5 |
C12—C11—C16 | 119.89 (17) | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 120.58 (17) | C13—O1—C18 | 116.90 (14) |
C16—C11—C10 | 119.46 (16) | C14—O2—C19 | 113.83 (14) |
C13—C12—C11 | 119.77 (17) | C15—O3—C20 | 116.82 (14) |
C13—C12—H12 | 120.1 | C8—S1—C1 | 91.12 (9) |
C11—C12—H12 | 120.1 | ||
C9—C1—C2—C3 | −176.81 (16) | C11—C12—C13—O1 | −177.52 (16) |
S1—C1—C2—C3 | 1.0 (2) | C11—C12—C13—C14 | 0.2 (3) |
C1—C2—C3—C4 | 178.70 (17) | O1—C13—C14—O2 | 2.7 (2) |
C1—C2—C3—C8 | −1.1 (2) | C12—C13—C14—O2 | −175.21 (15) |
C8—C3—C4—C5 | −0.2 (3) | O1—C13—C14—C15 | −179.89 (15) |
C2—C3—C4—C5 | −179.99 (18) | C12—C13—C14—C15 | 2.2 (3) |
C3—C4—C5—C6 | −0.3 (3) | O2—C14—C15—O3 | −4.6 (2) |
C4—C5—C6—C7 | 0.5 (3) | C13—C14—C15—O3 | 177.98 (15) |
C5—C6—C7—C8 | −0.3 (3) | O2—C14—C15—C16 | 174.93 (16) |
C6—C7—C8—C3 | −0.2 (3) | C13—C14—C15—C16 | −2.5 (3) |
C6—C7—C8—S1 | 179.34 (14) | O3—C15—C16—C11 | 179.89 (15) |
C4—C3—C8—C7 | 0.4 (3) | C14—C15—C16—C11 | 0.4 (3) |
C2—C3—C8—C7 | −179.74 (16) | C12—C11—C16—C15 | 2.1 (3) |
C4—C3—C8—S1 | −179.16 (13) | C10—C11—C16—C15 | −174.71 (16) |
C2—C3—C8—S1 | 0.7 (2) | C12—C13—O1—C18 | −8.9 (2) |
C2—C1—C9—C10 | 175.25 (18) | C14—C13—O1—C18 | 173.23 (15) |
S1—C1—C9—C10 | −2.3 (3) | C15—C14—O2—C19 | 101.4 (2) |
C1—C9—C10—C17 | 2.2 (3) | C13—C14—O2—C19 | −81.3 (2) |
C1—C9—C10—C11 | −174.59 (18) | C16—C15—O3—C20 | −5.3 (3) |
C9—C10—C11—C12 | 12.3 (3) | C14—C15—O3—C20 | 174.25 (15) |
C17—C10—C11—C12 | −164.64 (16) | C7—C8—S1—C1 | −179.64 (18) |
C9—C10—C11—C16 | −170.96 (16) | C3—C8—S1—C1 | −0.09 (14) |
C17—C10—C11—C16 | 12.1 (2) | C2—C1—S1—C8 | −0.55 (14) |
C16—C11—C12—C13 | −2.4 (3) | C9—C1—S1—C8 | 177.23 (17) |
C10—C11—C12—C13 | 174.38 (16) |
C19H15NO2S | F(000) = 672 |
Mr = 321.38 | Dx = 1.385 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3849 reflections |
a = 9.2958 (2) Å | θ = 1.0–27.5° |
b = 6.0830 (1) Å | µ = 0.22 mm−1 |
c = 27.2763 (7) Å | T = 90 K |
β = 92.1871 (10)° | Plate, pale yellow |
V = 1541.25 (6) Å3 | 0.27 × 0.22 × 0.06 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3528 independent reflections |
Radiation source: fine-focus sealed tube | 2288 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.5° |
ω scans at fixed χ = 55° | h = −11→12 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −7→7 |
Tmin = 0.943, Tmax = 0.987 | l = −35→35 |
6626 measured reflections |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0686P)2] where P = (Fo2 + 2Fc2)/3 |
3528 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C19H15NO2S | V = 1541.25 (6) Å3 |
Mr = 321.38 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2958 (2) Å | µ = 0.22 mm−1 |
b = 6.0830 (1) Å | T = 90 K |
c = 27.2763 (7) Å | 0.27 × 0.22 × 0.06 mm |
β = 92.1871 (10)° |
Nonius KappaCCD diffractometer | 3528 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 2288 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.987 | Rint = 0.052 |
6626 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.42 e Å−3 |
3528 reflections | Δρmin = −0.31 e Å−3 |
210 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 | ||
S1 | 0.38461 (5) | 0.47758 (9) | 0.124619 (19) | 0.02386 (18) | |
C1 | 0.4358 (2) | 0.3294 (3) | 0.07285 (7) | 0.0222 (5) | |
C2 | 0.5292 (2) | 0.6559 (4) | 0.11942 (7) | 0.0220 (5) | |
C3 | 0.5612 (2) | 0.8378 (4) | 0.14872 (8) | 0.0275 (5) | |
H3 | 0.5042 | 0.8729 | 0.1758 | 0.033* | |
C4 | 0.6774 (2) | 0.9657 (4) | 0.13743 (8) | 0.0299 (6) | |
H4 | 0.6995 | 1.0925 | 0.1566 | 0.036* | |
C5 | 0.7637 (2) | 0.9127 (4) | 0.09818 (8) | 0.0301 (6) | |
H5 | 0.8435 | 1.0036 | 0.0913 | 0.036* | |
C6 | 0.7346 (2) | 0.7308 (4) | 0.06940 (8) | 0.0278 (5) | |
H6 | 0.7946 | 0.6944 | 0.0432 | 0.033* | |
C7 | 0.6138 (2) | 0.5990 (4) | 0.07954 (7) | 0.0235 (5) | |
C8 | 0.5588 (2) | 0.4106 (4) | 0.05455 (8) | 0.0241 (5) | |
H8 | 0.6042 | 0.3467 | 0.0274 | 0.029* | |
C9 | 0.3577 (2) | 0.1446 (4) | 0.05200 (8) | 0.0241 (5) | |
H9 | 0.4014 | 0.0760 | 0.0251 | 0.029* | |
C10 | 0.2323 (2) | 0.0547 (3) | 0.06488 (7) | 0.0222 (5) | |
C11 | 0.1439 (2) | 0.1313 (4) | 0.10600 (7) | 0.0201 (5) | |
C12 | 0.1459 (2) | 0.0116 (3) | 0.14995 (7) | 0.0195 (5) | |
H12 | 0.2020 | −0.1185 | 0.1530 | 0.023* | |
C13 | 0.0666 (2) | 0.0820 (3) | 0.18888 (7) | 0.0182 (5) | |
C14 | −0.0166 (2) | 0.2740 (3) | 0.18395 (7) | 0.0194 (5) | |
C15 | −0.0195 (2) | 0.3904 (4) | 0.14021 (7) | 0.0208 (5) | |
H15 | −0.0765 | 0.5195 | 0.1368 | 0.025* | |
C16 | 0.0607 (2) | 0.3189 (3) | 0.10126 (7) | 0.0221 (5) | |
H16 | 0.0584 | 0.3992 | 0.0714 | 0.027* | |
C17 | 0.1769 (2) | −0.1288 (4) | 0.03658 (8) | 0.0258 (5) | |
N1 | 0.1309 (2) | −0.2751 (3) | 0.01413 (7) | 0.0380 (5) | |
O1 | 0.06264 (14) | −0.0206 (2) | 0.23333 (5) | 0.0212 (3) | |
C18 | 0.1533 (2) | −0.2088 (3) | 0.24029 (8) | 0.0260 (5) | |
H18A | 0.1276 | −0.3198 | 0.2154 | 0.039* | |
H18B | 0.1403 | −0.2702 | 0.2730 | 0.039* | |
H18C | 0.2541 | −0.1655 | 0.2372 | 0.039* | |
O2 | −0.08996 (14) | 0.3321 (2) | 0.22443 (5) | 0.0241 (4) | |
C19 | −0.1912 (2) | 0.5088 (4) | 0.21912 (8) | 0.0286 (5) | |
H19A | −0.1395 | 0.6465 | 0.2135 | 0.043* | |
H19B | −0.2456 | 0.5216 | 0.2491 | 0.043* | |
H19C | −0.2576 | 0.4793 | 0.1911 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0199 (3) | 0.0275 (3) | 0.0242 (3) | −0.0035 (2) | 0.0022 (2) | −0.0023 (2) |
C1 | 0.0205 (11) | 0.0252 (12) | 0.0208 (11) | 0.0023 (9) | −0.0006 (9) | 0.0028 (9) |
C2 | 0.0184 (11) | 0.0219 (12) | 0.0252 (11) | −0.0002 (9) | −0.0047 (9) | 0.0036 (10) |
C3 | 0.0229 (12) | 0.0279 (13) | 0.0315 (13) | −0.0007 (10) | −0.0027 (10) | −0.0006 (11) |
C4 | 0.0252 (12) | 0.0286 (14) | 0.0350 (13) | −0.0056 (10) | −0.0107 (10) | 0.0003 (10) |
C5 | 0.0200 (12) | 0.0333 (14) | 0.0364 (13) | −0.0056 (11) | −0.0061 (10) | 0.0110 (11) |
C6 | 0.0205 (12) | 0.0352 (14) | 0.0273 (12) | −0.0039 (10) | −0.0027 (9) | 0.0108 (11) |
C7 | 0.0195 (11) | 0.0271 (13) | 0.0235 (11) | 0.0004 (10) | −0.0027 (9) | 0.0075 (10) |
C8 | 0.0214 (11) | 0.0283 (13) | 0.0228 (11) | 0.0006 (10) | 0.0030 (9) | 0.0043 (10) |
C9 | 0.0260 (12) | 0.0252 (13) | 0.0213 (11) | 0.0020 (10) | 0.0030 (9) | −0.0011 (10) |
C10 | 0.0257 (12) | 0.0231 (12) | 0.0176 (10) | −0.0012 (10) | 0.0004 (9) | 0.0011 (9) |
C11 | 0.0170 (11) | 0.0222 (12) | 0.0209 (11) | −0.0044 (9) | −0.0010 (9) | −0.0012 (9) |
C12 | 0.0177 (11) | 0.0179 (11) | 0.0229 (11) | −0.0007 (9) | −0.0007 (9) | 0.0006 (9) |
C13 | 0.0160 (10) | 0.0196 (11) | 0.0188 (10) | −0.0028 (9) | −0.0025 (8) | 0.0022 (9) |
C14 | 0.0164 (10) | 0.0179 (11) | 0.0240 (11) | −0.0038 (9) | 0.0011 (9) | −0.0033 (9) |
C15 | 0.0166 (11) | 0.0188 (12) | 0.0266 (11) | −0.0007 (9) | −0.0026 (9) | 0.0037 (9) |
C16 | 0.0220 (11) | 0.0211 (12) | 0.0230 (11) | −0.0041 (9) | −0.0025 (9) | 0.0035 (9) |
C17 | 0.0295 (13) | 0.0282 (14) | 0.0201 (11) | −0.0050 (11) | 0.0068 (10) | 0.0017 (10) |
N1 | 0.0506 (13) | 0.0330 (13) | 0.0308 (11) | −0.0140 (11) | 0.0069 (10) | −0.0044 (10) |
O1 | 0.0234 (8) | 0.0204 (8) | 0.0199 (7) | 0.0031 (6) | 0.0024 (6) | 0.0030 (6) |
C18 | 0.0288 (12) | 0.0228 (12) | 0.0262 (12) | 0.0048 (10) | −0.0023 (10) | 0.0031 (10) |
O2 | 0.0214 (8) | 0.0215 (8) | 0.0297 (8) | 0.0048 (6) | 0.0065 (6) | 0.0009 (7) |
C19 | 0.0228 (12) | 0.0245 (13) | 0.0391 (13) | 0.0068 (10) | 0.0075 (10) | −0.0022 (10) |
S1—C2 | 1.737 (2) | C11—C16 | 1.382 (3) |
S1—C1 | 1.756 (2) | C11—C12 | 1.402 (3) |
C1—C8 | 1.358 (3) | C12—C13 | 1.383 (3) |
C1—C9 | 1.443 (3) | C12—H12 | 0.9500 |
C2—C3 | 1.391 (3) | C13—O1 | 1.365 (2) |
C2—C7 | 1.409 (3) | C13—C14 | 1.405 (3) |
C3—C4 | 1.376 (3) | C14—O2 | 1.366 (2) |
C3—H3 | 0.9500 | C14—C15 | 1.387 (3) |
C4—C5 | 1.400 (3) | C15—C16 | 1.391 (3) |
C4—H4 | 0.9500 | C15—H15 | 0.9500 |
C5—C6 | 1.377 (3) | C16—H16 | 0.9500 |
C5—H5 | 0.9500 | C17—N1 | 1.153 (3) |
C6—C7 | 1.416 (3) | O1—C18 | 1.430 (2) |
C6—H6 | 0.9500 | C18—H18A | 0.9800 |
C7—C8 | 1.419 (3) | C18—H18B | 0.9800 |
C8—H8 | 0.9500 | C18—H18C | 0.9800 |
C9—C10 | 1.346 (3) | O2—C19 | 1.432 (2) |
C9—H9 | 0.9500 | C19—H19A | 0.9800 |
C10—C17 | 1.441 (3) | C19—H19B | 0.9800 |
C10—C11 | 1.490 (3) | C19—H19C | 0.9800 |
C2—S1—C1 | 91.18 (10) | C16—C11—C10 | 120.68 (18) |
C8—C1—C9 | 123.8 (2) | C12—C11—C10 | 119.48 (19) |
C8—C1—S1 | 111.50 (17) | C13—C12—C11 | 120.40 (19) |
C9—C1—S1 | 124.67 (16) | C13—C12—H12 | 119.8 |
C3—C2—C7 | 121.7 (2) | C11—C12—H12 | 119.8 |
C3—C2—S1 | 126.79 (17) | O1—C13—C12 | 124.98 (18) |
C7—C2—S1 | 111.46 (16) | O1—C13—C14 | 115.58 (17) |
C4—C3—C2 | 118.3 (2) | C12—C13—C14 | 119.43 (18) |
C4—C3—H3 | 120.9 | O2—C14—C15 | 124.73 (19) |
C2—C3—H3 | 120.9 | O2—C14—C13 | 115.32 (18) |
C3—C4—C5 | 121.2 (2) | C15—C14—C13 | 119.95 (19) |
C3—C4—H4 | 119.4 | C14—C15—C16 | 120.3 (2) |
C5—C4—H4 | 119.4 | C14—C15—H15 | 119.9 |
C6—C5—C4 | 121.0 (2) | C16—C15—H15 | 119.9 |
C6—C5—H5 | 119.5 | C11—C16—C15 | 120.08 (19) |
C4—C5—H5 | 119.5 | C11—C16—H16 | 120.0 |
C5—C6—C7 | 118.9 (2) | C15—C16—H16 | 120.0 |
C5—C6—H6 | 120.5 | N1—C17—C10 | 179.2 (2) |
C7—C6—H6 | 120.5 | C13—O1—C18 | 116.63 (15) |
C2—C7—C6 | 118.8 (2) | O1—C18—H18A | 109.5 |
C2—C7—C8 | 111.60 (18) | O1—C18—H18B | 109.5 |
C6—C7—C8 | 129.6 (2) | H18A—C18—H18B | 109.5 |
C1—C8—C7 | 114.21 (19) | O1—C18—H18C | 109.5 |
C1—C8—H8 | 122.9 | H18A—C18—H18C | 109.5 |
C7—C8—H8 | 122.9 | H18B—C18—H18C | 109.5 |
C10—C9—C1 | 129.9 (2) | C14—O2—C19 | 117.29 (16) |
C10—C9—H9 | 115.1 | O2—C19—H19A | 109.5 |
C1—C9—H9 | 115.1 | O2—C19—H19B | 109.5 |
C9—C10—C17 | 118.05 (19) | H19A—C19—H19B | 109.5 |
C9—C10—C11 | 125.2 (2) | O2—C19—H19C | 109.5 |
C17—C10—C11 | 116.69 (18) | H19A—C19—H19C | 109.5 |
C16—C11—C12 | 119.84 (19) | H19B—C19—H19C | 109.5 |
C2—S1—C1—C8 | 1.94 (17) | C1—C9—C10—C11 | −0.5 (4) |
C2—S1—C1—C9 | −177.93 (18) | C9—C10—C11—C16 | 76.2 (3) |
C1—S1—C2—C3 | 177.43 (19) | C17—C10—C11—C16 | −103.0 (2) |
C1—S1—C2—C7 | −0.84 (16) | C9—C10—C11—C12 | −103.6 (3) |
C7—C2—C3—C4 | 1.1 (3) | C17—C10—C11—C12 | 77.2 (3) |
S1—C2—C3—C4 | −177.03 (16) | C16—C11—C12—C13 | −0.9 (3) |
C2—C3—C4—C5 | −1.3 (3) | C10—C11—C12—C13 | 178.86 (18) |
C3—C4—C5—C6 | 0.3 (3) | C11—C12—C13—O1 | −179.09 (18) |
C4—C5—C6—C7 | 1.1 (3) | C11—C12—C13—C14 | 0.3 (3) |
C3—C2—C7—C6 | 0.2 (3) | O1—C13—C14—O2 | 0.1 (2) |
S1—C2—C7—C6 | 178.62 (15) | C12—C13—C14—O2 | −179.31 (17) |
C3—C2—C7—C8 | −178.78 (19) | O1—C13—C14—C15 | 179.88 (17) |
S1—C2—C7—C8 | −0.4 (2) | C12—C13—C14—C15 | 0.4 (3) |
C5—C6—C7—C2 | −1.3 (3) | O2—C14—C15—C16 | 179.14 (18) |
C5—C6—C7—C8 | 177.5 (2) | C13—C14—C15—C16 | −0.6 (3) |
C9—C1—C8—C7 | 177.30 (19) | C12—C11—C16—C15 | 0.8 (3) |
S1—C1—C8—C7 | −2.6 (2) | C10—C11—C16—C15 | −179.01 (19) |
C2—C7—C8—C1 | 1.9 (3) | C14—C15—C16—C11 | 0.0 (3) |
C6—C7—C8—C1 | −176.9 (2) | C12—C13—O1—C18 | 3.1 (3) |
C8—C1—C9—C10 | −176.5 (2) | C14—C13—O1—C18 | −176.31 (16) |
S1—C1—C9—C10 | 3.3 (3) | C15—C14—O2—C19 | 8.5 (3) |
C1—C9—C10—C17 | 178.7 (2) | C13—C14—O2—C19 | −171.76 (17) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C20H17NO3S | C19H15NO2S |
Mr | 351.41 | 321.38 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 90 | 90 |
a, b, c (Å) | 7.4136 (1), 23.4782 (3), 10.3932 (2) | 9.2958 (2), 6.0830 (1), 27.2763 (7) |
β (°) | 110.3689 (6) | 92.1871 (10) |
V (Å3) | 1695.90 (5) | 1541.25 (6) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.21 | 0.22 |
Crystal size (mm) | 0.40 × 0.15 × 0.15 | 0.27 × 0.22 × 0.06 |
Data collection | ||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.921, 0.969 | 0.943, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7649, 3894, 2800 | 6626, 3528, 2288 |
Rint | 0.037 | 0.052 |
(sin θ/λ)max (Å−1) | 0.650 | 0.649 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.127, 1.07 | 0.047, 0.127, 1.00 |
No. of reflections | 3894 | 3528 |
No. of parameters | 229 | 210 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.29 | 0.42, −0.31 |
Computer programs: COLLECT (Nonius, 1999), DENZO-SMN (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1995), SHELXL97 (Sheldrick, 1997) and local procedures, SHELX97-2 (Sheldrick, 1997) and local procedures.
C1—S1 | 1.7519 (18) | C15—O3 | 1.368 (2) |
C8—S1 | 1.7328 (19) | C17—N1 | 1.149 (2) |
C10—C17 | 1.437 (2) | C19—O2 | 1.426 (2) |
C10—C11 | 1.480 (2) | C20—O3 | 1.431 (2) |
C14—O2 | 1.376 (2) | ||
C9—C10—C17 | 119.79 (16) | C14—O2—C19 | 113.83 (14) |
O2—C14—C13 | 120.61 (16) | C15—O3—C20 | 116.82 (14) |
N1—C17—C10 | 177.9 (2) | C8—S1—C1 | 91.12 (9) |
C2—C1—C9—C10 | 175.25 (18) | C1—C9—C10—C17 | 2.2 (3) |
S1—C1—C9—C10 | −2.3 (3) | C1—C9—C10—C11 | −174.59 (18) |
S1—C2 | 1.737 (2) | C14—O2 | 1.366 (2) |
S1—C1 | 1.756 (2) | C17—N1 | 1.153 (3) |
C10—C17 | 1.441 (3) | O2—C19 | 1.432 (2) |
C10—C11 | 1.490 (3) | ||
C2—S1—C1 | 91.18 (10) | C13—O1—C18 | 116.63 (15) |
C9—C10—C17 | 118.05 (19) | C14—O2—C19 | 117.29 (16) |
N1—C17—C10 | 179.2 (2) | ||
C8—C1—C9—C10 | −176.5 (2) | C1—C9—C10—C17 | 178.7 (2) |
S1—C1—C9—C10 | 3.3 (3) | C1—C9—C10—C11 | −0.5 (4) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
2,3-Diarylacrylonitriles are very important synthons for the synthesis of a wide spectrum of biologically active molecules (Loupy et al., 2005). These compounds have been shown to possess spasmolytic, estrogenic, hypotensive, antioxidative, tuberculostatic, antitrichomonal, insecticidal and cytotoxic activities (Saczewski et al., 2004). Compounds of general structure 1 undergo interconversion to the corresponding E isomer in solution under certain conditions, which is dependent on the nature of the two groups linked across the double bond carrying the nitrile group, i.e. whether π-excessive (donating) or π-deficient (accepting). Normally, base-catalyzed condensation of aryl/heteroarylaldehydes with aryl/heteroarylacetonitriles leads to the formation of the Z isomer, but isomerism to the E form can be readily monitored by NMR studies. In connection with our ongoing research, we have undertaken the synthesis of a series of novel substituted aryl/heteroarylacrylonitriles. Compounds (I) and (II) were prepared by the reaction of benzo[b]thiophene-2-carboxaldehyde with 3,4,5-trimethoxyphenylacetonitrile and 3,4-dimethoxyphenylacetonitrile in the presence of methanolic potassium hydroxide under reflux. In order to obtain detailed information on the structural conformation of these molecules and to confirm the geometry, their X-ray structure determination has been carried out. Recrystallization from ethyl acetate afforded yellow needles of (I) that were suitable for X-ray analysis, but (II) afforded yellow silky needles that were not suitable for X-ray analysis. Furthermore, when (II) was crystallized from a mixture of ethyl acetate and chloroform by slow evaporation at room temperature over a period of one week, a mixture of yellow crystals (fine silky crystals as well as crystalline hexagons) were obtained.
The molecular structure and the atom-numbering scheme of (I) is shown in Fig. 1; selected bond lengths and angles are listed in Table 1. In (I), the olefinic bond connecting the 3,4,5-trimethoxyphenyl and benzo[b]thiophene rings has the E geometry. Significant deviations from the ideal bond-angle geometry around the Csp2 atoms of the double bond are observed. The C11—C10—C17, C10═C9—C1, and C9—C1—S1 bond angles [115.92 (16)°, 130.57 (17)°, and 125.51 (14)° respectively] are distorted owing to steric hindrance of the double bond linking the two ring systems. Neither the benzo[b]thiophene ring nor the phenyl ring of the 3,4,5-trimethoxyphenyl group is coplanar with the vinyl double bond, making a dihedral angle of 5.2 (3) and 13.1 (2)° respectively. The C9═C10 double bond [1.366 (2) Å] in (I) is slightly larger than that observed in the disubstituted olefinic group of 2-styrylbenzimidazole [1.304 (4) Å; Bacelo et al., 1997], suggesting some delocalization in the unsaturated bridging units. This fact is further supported by the C1—C9 bond length [1.443 (2) Å], which is slightly shorter than the Car—Csp2 single bond (Wilson, 1992), suggesting extensive conjugation between the π-electron system of the benzo[b]thiophene and the central double bond.
The observed O—C bond lengths are in agreement with values found for the aromatic methoxy group. There is an asymmetry of the exocyclic angles at atoms C13 and C15 [O1—C13—C12/O1—C13—C14 = 124.09 (16)/115.20 (15)°] and [O3—C15—C16/O3—C15—C14 = 124.20 (16)/115.42 (15)°]. This is caused by the tendency of the methoxy group to be coplanar with the benzene ring, owing to conjugation of the O1 and O3 lone pairs with the benzene ring (Domiano et al., 1979). However, the exocyclic angles [C15—C14—O2/C13—C14—O2 = 120.21 (16)/120.61 (16)°] at atom C14 are symmetric because of the influence of the adjacent methoxy groups, which force the O—C bond of the central methoxy group out of the plane of the aromatic ring at an angle that is approximately perpendicular to the plane of the aromatic ring, affording an almost symmetrical structure. This is contrary to what is observed with a single methoxy substituent at this position on the aromatic ring (Sonar et al., 2006), where the O—C bond of the methoxy group is coplanar with the aromatic ring, resulting in asymmetry in the aromatic ring and a consequent difference in the exocyclic angles adjacent to the methoxy group.
Fig. 2 shows an ellipsoid plot of (II), and selected geometric parameters are presented in Table 2. The olefinic bond connecting the 3,4-dimethoxyphenyl and benzo[b]thiophene rings in compound (II) has the Z-geometry. The bond angles around the Csp2 atoms are distorted from the standard value (120°). The C11—C10—C17, C10═C9—C1 and C9—C10—C11 bond angles [116.69 (18)°, 129.9 (2)°, and 125.2 (2)° respectively] are distorted owing to steric hindrance of the double bond linking the two ring systems. The plane of the 3,4-dimethoxyphenyl ring is twisted with respect to the plane of the benzo[b]thiophene ring. The 3,4-dimethoxyphenyl and benzo[b]thiophene planes make dihedral angles of 76.09 (7) and 4.84 (17)° respectively, with the plane of the central vinyl moiety. In compound (II), the bridging unit C9═C10 [1.346 (3) Å] is slightly larger than expected [1.304 (4) Å; Bacelo et al., 1997]. However, the C1—C9 bond length [1.443 (2) Å] is slightly shorter than a typical Car—Csp2 single bond (Wilson, 1992), suggesting extensive conjugation between the π-electron system of the benzo[b]thiophene and the central double bond.
The observed O—C bond lengths are in agreement with values found for anisoles. There is an asymmetry of the exocyclic angles at C13 and C14 [O1—C13—C12/O1—C13—C14 = 124.98 (18)/115.58 (17)°] and [O2—C14—C15/O2—C14—C13 = 124.73 (19)/115.23 (18)°]. This is caused by the tendency of the methoxy group to be coplanar with the benzene ring, owing to conjugation of the O1 and O2 lone pairs with the benzene ring (Domiano et al., 1979).
There are no significant intermolecular hydrogen-bonding interactions in the packing of (I) and (II). The packing is essentially stabilized via van der Waals forces.