4-(Di­phenyl­meth­oxy)-3-eth­oxy­benzaldehyde

Samoľová, E.; Dehno Khalaji, A.; Eigner, V.

doi:10.1107/S2414314621003564

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 4| April 2021| x210356

https://doi.org/10.1107/S2414314621003564

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4-(Diphenylmethoxy)-3-ethoxybenzaldehyde

Erika Samoľová,^a ^* Aliakbar Dehno Khalaji ^b and Václav Eigner ^a

^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 18 March 2021; accepted 1 April 2021; online 9 April 2021)

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.

Keywords: Schiff bases; crystal structure; weak intermolecular interactions.

CCDC reference: 2075001

Structure description

The preparation of Schiff bases (Omidi & Kakanejadifard, 2020 ) 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 Schiff bases and we now describe its crystal structure (Fig. 1).

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

As 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 C5^iv—H1c5^iv⋯Cg3 = 2.89 Å; symmetry codes: (iii) $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, z; (iv) x − $[{1\over 2}]$ , y, $[{1\over 2}]$ − 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).

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Figure 2
Partial packing diagram showing the hydrogen bonds in the title compound. Hydrogen atoms not involved in hydrogen bonding were omitted for clarity. Symmetry codes: (i) −x + 1, y + $[{1\over 2}]$ , −z + 1; (ii) x − 1, y, z; (iii) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , z.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₀O₃
M_r	332.4
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	8.1123 (4), 15.8713 (9), 27.6155 (14)
V (Å³)	3555.6 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.83 × 0.32 × 0.26

Data collection
Diffractometer	Rigaku Oxford Diffraction Xcalibur, AtlasS2, Gemini ultra
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.958, 0.982
No. of measured, independent and observed [I > 3σ(I)] reflections	16215, 4454, 3284
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.44
No. of reflections	4454
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SUPERFLIP (Palatinus & Chapuis, (2007 ), JANA2006 (Petříček et al., 2014 ) and DIAMOND (Brandenburg, 1999 ).

Structural data

CCDC reference: 2075001

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314621003564/hb4378sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003564/hb4378Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: 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).

4-(Diphenylmethoxy)-3-ethoxybenzaldehyde top

Crystal data top

C₂₂H₂₀O₃	F(000) = 1408
M_r = 332.4	D_x = 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

Data collection top

Rigaku Oxford Diffraction Xcalibur, AtlasS2, Gemini ultra diffractometer	4454 independent reflections
Radiation source: X-ray tube	3284 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 5.1783 pixels mm^-1	θ_max = 29.6°, θ_min = 3.6°
ω scans	h = −11→8
Absorption correction: analytical (CrysalisPro; Rigaku OD, 2015)	k = −20→20
T_min = 0.958, T_max = 0.982	l = −37→37
16215 measured reflections

Refinement top

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	Δρ_max = 0.22 e Å⁻³
4454 reflections	Δρ_min = −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

Special details top

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 U_iso(H) = 1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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