organic compounds
4-(Diphenylmethoxy)-3-ethoxybenzaldehyde
aInstitute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran
*Correspondence e-mail: samolova@fzu.cz
In the title compound, C22H20O3, the dihedral angle between the aromatic rings linked by the methine group is 81.265 (4)° and the ethoxy side chain adopts an extended conformation [C—O—C—C = 177.24 (10)°]. In the crystal, weak C—H⋯π and C—H⋯O interactions link the molecules into sheets.
CCDC reference: 2075001
Structure description
The preparation of ) is nowadays an interesting topic, because of their various application and properties (e.g., Kizilkaya et al., 2020). As part of our studies in this area, the title aldehyde, C22H20O3, was prepared as a precursor to new and we now describe its (Fig. 1).
(Omidi & Kakanejadifard, 2020As expected, the C2—O2, C20—O2, C1—O1 and C7—O1 bond lengths reveal single bond character while C22=O3 is a double bond. The dihedral angle between the C1–C6 and C8–C13 aromatic rings connected by the C7 methine group is 81.265 (4)°. In the crystal, weak C—H⋯O (Table 1) and C—H⋯π interactions [C20iii—H1c20iii⋯Cg3 = 3.05 Å and C5iv—H1c5iv⋯Cg3 = 2.89 Å; symmetry codes: (iii) − x, + y, z; (iv) x − , y, − z; Cg3 is the centroid of the C14–C19 ring] are observed. These link the molecules into sheets lying perpendicular to the c-axis direction (Fig. 2).
Synthesis and crystallization
3-Ethoxy-4-hydroxy benzaldehyde (0.20 mmol) and potassium carbonate (0.40 mmol) were mixed in dimethylformamide (25 ml) and stirred for 0.5 h. A solution of diphenylbromomethane (0.2 mmol) in ethanol (20 ml) was added dropwise and the mixture was stirred at 80°C for 24 h. After that, the solution was concentrated under reduced pressure. The cream precipitate of the title compound formed by adding cold water (250 ml) was filtered off and washed several times with cold ethanol. Colourless slabs were recrystallized from the mixed solvents of chloroform and ethanol (1:1).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2075001
https://doi.org/10.1107/S2414314621003564/hb4378sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003564/hb4378Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: Superflip (Palatinus & Chapuis, (2007); program(s) used to refine structure: Jana2006 (Petříček et al., 2014); molecular graphics: DIAMOND (Brandenburg, 1999).C22H20O3 | F(000) = 1408 |
Mr = 332.4 | Dx = 1.242 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P -2xab;-2ybc;-2zac | Cell parameters from 4539 reflections |
a = 8.1123 (4) Å | θ = 3.9–29.2° |
b = 15.8713 (9) Å | µ = 0.08 mm−1 |
c = 27.6155 (14) Å | T = 120 K |
V = 3555.6 (3) Å3 | Plate, colourless |
Z = 8 | 0.83 × 0.32 × 0.26 mm |
Rigaku Oxford Diffraction Xcalibur, AtlasS2, Gemini ultra diffractometer | 4454 independent reflections |
Radiation source: X-ray tube | 3284 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 5.1783 pixels mm-1 | θmax = 29.6°, θmin = 3.6° |
ω scans | h = −11→8 |
Absorption correction: analytical (CrysalisPro; Rigaku OD, 2015) | k = −20→20 |
Tmin = 0.958, Tmax = 0.982 | l = −37→37 |
16215 measured reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.107 | (Δ/σ)max = 0.0004 |
S = 1.44 | Δρmax = 0.22 e Å−3 |
4454 reflections | Δρmin = −0.20 e Å−3 |
227 parameters | Extinction correction: B-C type 1 Gaussian isotropic [Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129–147] |
0 restraints | Extinction coefficient: 13000 (2000) |
80 constraints |
Refinement. All hydrogen atoms were discernible in difference Fourier maps and could be refined to reasonable geometry, but according to common practice they were refined as riding atoms with C—H = 0.96 Å and Uiso(H) = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.34686 (10) | 0.62710 (5) | 0.13059 (3) | 0.0193 (2) | |
O2 | 0.52510 (10) | 0.49847 (5) | 0.11100 (3) | 0.0203 (2) | |
O3 | 0.64458 (13) | 0.36127 (6) | 0.27937 (3) | 0.0385 (3) | |
C1 | 0.38844 (13) | 0.57930 (7) | 0.16975 (4) | 0.0170 (3) | |
C2 | 0.48965 (13) | 0.50922 (7) | 0.15898 (4) | 0.0170 (3) | |
C3 | 0.54565 (14) | 0.45894 (7) | 0.19596 (4) | 0.0195 (3) | |
C4 | 0.50097 (14) | 0.47681 (7) | 0.24410 (4) | 0.0205 (3) | |
C5 | 0.40159 (14) | 0.54531 (8) | 0.25426 (4) | 0.0206 (3) | |
C6 | 0.34409 (14) | 0.59647 (8) | 0.21712 (4) | 0.0198 (3) | |
C7 | 0.27297 (14) | 0.70813 (7) | 0.13914 (4) | 0.0171 (3) | |
C8 | 0.32021 (13) | 0.76454 (7) | 0.09687 (4) | 0.0178 (3) | |
C9 | 0.39897 (15) | 0.73419 (8) | 0.05577 (4) | 0.0261 (4) | |
C10 | 0.43962 (18) | 0.78854 (9) | 0.01835 (5) | 0.0326 (4) | |
C11 | 0.40310 (16) | 0.87355 (9) | 0.02180 (5) | 0.0297 (4) | |
C12 | 0.32477 (15) | 0.90430 (9) | 0.06254 (5) | 0.0261 (4) | |
C13 | 0.28374 (14) | 0.85001 (8) | 0.10003 (4) | 0.0218 (4) | |
C14 | 0.08714 (14) | 0.70028 (7) | 0.14420 (4) | 0.0177 (3) | |
C15 | −0.00177 (15) | 0.65479 (8) | 0.11019 (5) | 0.0256 (4) | |
C16 | −0.17290 (16) | 0.65229 (9) | 0.11241 (5) | 0.0322 (4) | |
C17 | −0.25477 (16) | 0.69522 (8) | 0.14866 (5) | 0.0298 (4) | |
C18 | −0.16734 (15) | 0.73910 (8) | 0.18332 (5) | 0.0250 (4) | |
C19 | 0.00414 (14) | 0.74156 (7) | 0.18104 (4) | 0.0199 (3) | |
C20 | 0.63310 (15) | 0.43012 (8) | 0.09834 (4) | 0.0245 (4) | |
C21 | 0.64587 (17) | 0.42893 (9) | 0.04403 (5) | 0.0316 (4) | |
C22 | 0.55991 (16) | 0.42412 (8) | 0.28389 (5) | 0.0275 (4) | |
H1c3 | 0.615307 | 0.411587 | 0.188954 | 0.0233* | |
H1c5 | 0.37214 | 0.557585 | 0.287186 | 0.0248* | |
H1c6 | 0.273891 | 0.643544 | 0.22428 | 0.0237* | |
H1c7 | 0.312056 | 0.732024 | 0.168939 | 0.0205* | |
H1c9 | 0.425323 | 0.675383 | 0.053266 | 0.0313* | |
H1c10 | 0.493341 | 0.767159 | −0.010079 | 0.0391* | |
H1c11 | 0.432179 | 0.911071 | −0.004095 | 0.0357* | |
H1c12 | 0.298754 | 0.963157 | 0.06492 | 0.0313* | |
H1c13 | 0.22977 | 0.871597 | 0.128373 | 0.0261* | |
H1c15 | 0.055107 | 0.624903 | 0.085003 | 0.0307* | |
H1c16 | −0.23405 | 0.620772 | 0.088795 | 0.0386* | |
H1c17 | −0.373047 | 0.694527 | 0.149741 | 0.0357* | |
H1c18 | −0.224467 | 0.767824 | 0.208906 | 0.0301* | |
H1c19 | 0.065108 | 0.772039 | 0.205141 | 0.0239* | |
H1c20 | 0.586452 | 0.377955 | 0.10939 | 0.0294* | |
H2c20 | 0.740136 | 0.439896 | 0.112063 | 0.0294* | |
H1c21 | 0.719041 | 0.384571 | 0.034222 | 0.0379* | |
H2c21 | 0.538733 | 0.419448 | 0.030313 | 0.0379* | |
H3c21 | 0.687979 | 0.482033 | 0.032892 | 0.0379* | |
H1c22 | 0.529438 | 0.440345 | 0.316162 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0248 (4) | 0.0172 (4) | 0.0158 (4) | 0.0056 (3) | −0.0024 (3) | 0.0000 (3) |
O2 | 0.0249 (4) | 0.0180 (4) | 0.0180 (4) | 0.0037 (3) | 0.0006 (3) | −0.0005 (3) |
O3 | 0.0567 (6) | 0.0310 (6) | 0.0277 (5) | 0.0151 (5) | −0.0056 (4) | 0.0064 (4) |
C1 | 0.0164 (5) | 0.0162 (6) | 0.0185 (6) | −0.0025 (5) | −0.0032 (4) | 0.0020 (4) |
C2 | 0.0181 (5) | 0.0164 (6) | 0.0165 (5) | −0.0037 (5) | −0.0010 (4) | −0.0009 (4) |
C3 | 0.0207 (6) | 0.0160 (6) | 0.0217 (6) | −0.0001 (5) | −0.0018 (5) | 0.0006 (4) |
C4 | 0.0219 (6) | 0.0190 (6) | 0.0205 (6) | −0.0036 (5) | −0.0029 (5) | 0.0032 (5) |
C5 | 0.0220 (6) | 0.0219 (6) | 0.0180 (6) | −0.0037 (5) | −0.0007 (5) | 0.0006 (5) |
C6 | 0.0188 (5) | 0.0197 (6) | 0.0208 (6) | 0.0006 (5) | 0.0000 (4) | −0.0005 (5) |
C7 | 0.0197 (6) | 0.0151 (6) | 0.0164 (5) | 0.0019 (5) | −0.0028 (4) | −0.0022 (4) |
C8 | 0.0143 (5) | 0.0208 (6) | 0.0182 (5) | −0.0004 (5) | −0.0042 (4) | 0.0004 (4) |
C9 | 0.0328 (7) | 0.0224 (7) | 0.0230 (6) | 0.0036 (6) | 0.0031 (5) | 0.0003 (5) |
C10 | 0.0405 (8) | 0.0327 (8) | 0.0245 (7) | 0.0045 (6) | 0.0101 (6) | 0.0017 (6) |
C11 | 0.0326 (7) | 0.0299 (7) | 0.0267 (7) | −0.0012 (6) | 0.0039 (5) | 0.0093 (6) |
C12 | 0.0280 (6) | 0.0200 (7) | 0.0304 (7) | 0.0006 (5) | −0.0002 (5) | 0.0033 (5) |
C13 | 0.0218 (6) | 0.0211 (6) | 0.0225 (6) | 0.0012 (5) | 0.0008 (5) | −0.0010 (5) |
C14 | 0.0190 (5) | 0.0145 (6) | 0.0195 (6) | −0.0008 (5) | −0.0033 (4) | 0.0050 (4) |
C15 | 0.0268 (7) | 0.0270 (7) | 0.0230 (7) | −0.0037 (5) | −0.0032 (5) | −0.0009 (5) |
C16 | 0.0279 (7) | 0.0352 (8) | 0.0335 (8) | −0.0112 (6) | −0.0109 (6) | 0.0019 (6) |
C17 | 0.0178 (6) | 0.0313 (7) | 0.0402 (7) | −0.0048 (6) | −0.0016 (5) | 0.0120 (6) |
C18 | 0.0234 (6) | 0.0210 (6) | 0.0307 (7) | 0.0010 (5) | 0.0053 (5) | 0.0076 (5) |
C19 | 0.0222 (6) | 0.0167 (6) | 0.0208 (6) | −0.0010 (5) | −0.0011 (5) | 0.0029 (5) |
C20 | 0.0256 (6) | 0.0223 (6) | 0.0257 (6) | 0.0064 (5) | 0.0022 (5) | −0.0009 (5) |
C21 | 0.0347 (7) | 0.0333 (8) | 0.0267 (7) | 0.0066 (6) | 0.0065 (6) | −0.0034 (6) |
C22 | 0.0347 (7) | 0.0257 (7) | 0.0221 (7) | 0.0013 (6) | −0.0025 (5) | 0.0035 (5) |
O1—C1 | 1.3632 (13) | C11—C12 | 1.3813 (18) |
O1—C7 | 1.4380 (13) | C11—H1c11 | 0.96 |
O2—C2 | 1.3662 (13) | C12—C13 | 1.3873 (18) |
O2—C20 | 1.4377 (14) | C12—H1c12 | 0.96 |
O3—C22 | 1.2174 (16) | C13—H1c13 | 0.96 |
C1—C2 | 1.4142 (15) | C14—C15 | 1.3870 (17) |
C1—C6 | 1.3838 (16) | C14—C19 | 1.3845 (16) |
C2—C3 | 1.3736 (16) | C15—C16 | 1.3902 (18) |
C3—C4 | 1.4067 (16) | C15—H1c15 | 0.96 |
C3—H1c3 | 0.96 | C16—C17 | 1.3809 (19) |
C4—C5 | 1.3821 (16) | C16—H1c16 | 0.96 |
C4—C22 | 1.4614 (17) | C17—C18 | 1.3807 (18) |
C5—C6 | 1.3892 (16) | C17—H1c17 | 0.96 |
C5—H1c5 | 0.96 | C18—C19 | 1.3931 (17) |
C6—H1c6 | 0.96 | C18—H1c18 | 0.96 |
C7—C8 | 1.5202 (16) | C19—H1c19 | 0.96 |
C7—C14 | 1.5192 (16) | C20—C21 | 1.5034 (17) |
C7—H1c7 | 0.96 | C20—H1c20 | 0.96 |
C8—C9 | 1.3885 (17) | C20—H2c20 | 0.96 |
C8—C13 | 1.3911 (17) | C21—H1c21 | 0.96 |
C9—C10 | 1.3865 (18) | C21—H2c21 | 0.96 |
C9—H1c9 | 0.96 | C21—H3c21 | 0.96 |
C10—C11 | 1.3843 (19) | C22—H1c22 | 0.96 |
C10—H1c10 | 0.96 | ||
C1—O1—C7 | 118.07 (8) | C11—C12—H1c12 | 120.04 |
C2—O2—C20 | 117.29 (9) | C13—C12—H1c12 | 120.04 |
O1—C1—C2 | 114.48 (9) | C8—C13—C12 | 120.52 (11) |
O1—C1—C6 | 125.17 (10) | C8—C13—H1c13 | 119.74 |
C2—C1—C6 | 120.32 (10) | C12—C13—H1c13 | 119.74 |
O2—C2—C1 | 115.12 (9) | C7—C14—C15 | 119.76 (10) |
O2—C2—C3 | 125.37 (10) | C7—C14—C19 | 120.76 (10) |
C1—C2—C3 | 119.51 (10) | C15—C14—C19 | 119.40 (10) |
C2—C3—C4 | 120.02 (10) | C14—C15—C16 | 120.29 (12) |
C2—C3—H1c3 | 119.99 | C14—C15—H1c15 | 119.86 |
C4—C3—H1c3 | 119.99 | C16—C15—H1c15 | 119.86 |
C3—C4—C5 | 120.07 (11) | C15—C16—C17 | 119.88 (12) |
C3—C4—C22 | 120.72 (11) | C15—C16—H1c16 | 120.06 |
C5—C4—C22 | 119.22 (11) | C17—C16—H1c16 | 120.06 |
C4—C5—C6 | 120.37 (11) | C16—C17—C18 | 120.30 (12) |
C4—C5—H1c5 | 119.81 | C16—C17—H1c17 | 119.85 |
C6—C5—H1c5 | 119.81 | C18—C17—H1c17 | 119.85 |
C1—C6—C5 | 119.71 (11) | C17—C18—C19 | 119.70 (11) |
C1—C6—H1c6 | 120.14 | C17—C18—H1c18 | 120.15 |
C5—C6—H1c6 | 120.14 | C19—C18—H1c18 | 120.15 |
O1—C7—C8 | 107.20 (8) | C14—C19—C18 | 120.39 (11) |
O1—C7—C14 | 110.82 (9) | C14—C19—H1c19 | 119.8 |
O1—C7—H1c7 | 110.86 | C18—C19—H1c19 | 119.8 |
C8—C7—C14 | 111.65 (9) | O2—C20—C21 | 107.10 (10) |
C8—C7—H1c7 | 110.01 | O2—C20—H1c20 | 109.47 |
C14—C7—H1c7 | 106.34 | O2—C20—H2c20 | 109.47 |
C7—C8—C9 | 122.61 (10) | C21—C20—H1c20 | 109.47 |
C7—C8—C13 | 118.21 (10) | C21—C20—H2c20 | 109.47 |
C9—C8—C13 | 119.18 (11) | H1c20—C20—H2c20 | 111.74 |
C8—C9—C10 | 120.17 (12) | C20—C21—H1c21 | 109.47 |
C8—C9—H1c9 | 119.91 | C20—C21—H2c21 | 109.47 |
C10—C9—H1c9 | 119.91 | C20—C21—H3c21 | 109.47 |
C9—C10—C11 | 120.28 (12) | H1c21—C21—H2c21 | 109.47 |
C9—C10—H1c10 | 119.86 | H1c21—C21—H3c21 | 109.47 |
C11—C10—H1c10 | 119.86 | H2c21—C21—H3c21 | 109.47 |
C10—C11—C12 | 119.93 (12) | O3—C22—C4 | 125.21 (12) |
C10—C11—H1c11 | 120.04 | O3—C22—H1c22 | 117.39 |
C12—C11—H1c11 | 120.04 | C4—C22—H1c22 | 117.4 |
C11—C12—C13 | 119.91 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H1c7···O3i | 0.96 | 2.52 | 3.3794 (15) | 148 |
C17—H1c17···O1ii | 0.96 | 2.57 | 3.4440 (15) | 152 |
C18—H1c18···O3iii | 0.96 | 2.53 | 3.2906 (16) | 136 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1/2, y+1/2, z. |
Acknowledgements
The authors are grateful to Golestan University. CzechNanoLab project LM2018110 funded by MEYS CR is gratefully acknowledged for the financial support of the measurements at LNSM Research Infrastructure.
References
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Kizilkaya, H., Dag, B., Aral, T., Genc, N. & Erenler, R. (2020). J. Chin. Chem. Soc. 67, 1696–1701. Web of Science CrossRef CAS Google Scholar
Omidi, S. & Kakanejadifard, A. (2020). RSC Adv. 10, 30186–30202. Web of Science CrossRef CAS Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345–352. Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
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