1-(4-Carboethoxy­phenyl­methyl)-2-ethoxy­naphthalene

Oloo, E.O.; Quail, J.W.; Padmanilayam, M.P.; Dimmock, J.R.

doi:10.1107/S160053680200867X

1-(4-Carboethoxyphenylmethyl)-2-ethoxynaphthalene

E. O. Oloo, J. W. Quail, M. P. Padmanilayam and J. R. Dimmock

While attempting to prepare the ethyl ester of (E)-1-(4-carboxyphenylmethylene)-2-tetralone, (I), C₁₈H₁₄O₃, the unexpected product 1-(4-carboethoxyphenylmethyl)-2-ethoxynaphthalene, (II), C₂₂H₂₂O₃, was obtained. Compound (II) crystallizes in space group P $\overline 1$ , with molecules paired by π-stacking of the naphthalene moieties around inversion centres.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200867X/cf6179sup1.cif Contains datablocks II, lene
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680200867X/cf6179IIsup2.hkl Contains datablock II

CCDC reference: 189410

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
R factor = 0.059
wR factor = 0.158
Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: Xtal3.7 (Hall et al., 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal3.7; software used to prepare material for publication: SHELXL97.

1-(4-carboethoxyphenylmethyl)-2-ethoxynaphthalene top

Crystal data top

C₂₂H₂₂O₃	Z = 2
M_r = 334.40	F(000) = 356
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Melting point = 357–358 K
a = 8.947 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.109 (2) Å	Cell parameters from 25 reflections
c = 12.495 (3) Å	θ = 9.1–18.3°
α = 90.87 (2)°	µ = 0.09 mm⁻¹
β = 104.15 (2)°	T = 150 K
γ = 118.17 (2)°	Prism, colourless
V = 860.2 (5) Å³	0.30 × 0.30 × 0.10 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.022
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.9°
Graphite monochromator	h = −10→10
ω scans	k = −10→10
3385 measured reflections	l = −14→3
3025 independent reflections	3 standard reflections every 120 min
1482 reflections with I > 2σ(I)	intensity decay: <2%

Refinement top

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0655P)²] where P = (F_o² + 2F_c²)/3
3025 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.3895 (3)	0.2160 (3)	0.4664 (2)	0.0270 (6)
O2	0.3882 (4)	0.1441 (4)	1.1121 (2)	0.0433 (8)
O3	0.2399 (3)	−0.0932 (3)	0.9869 (2)	0.0332 (7)
C1	0.5647 (4)	0.2586 (4)	0.5011 (3)	0.0228 (8)
C2	0.6637 (4)	0.3701 (4)	0.6003 (3)	0.0210 (8)
C3	0.8450 (5)	0.4158 (4)	0.6432 (3)	0.0234 (8)
C4	0.9576 (5)	0.5297 (4)	0.7438 (3)	0.0271 (9)
H4	0.9104	0.5765	0.7856	0.032*
C5	1.1317 (5)	0.5731 (5)	0.7814 (3)	0.0297 (9)
H5	1.2043	0.6519	0.8477	0.036*
C6	1.2058 (5)	0.5031 (5)	0.7236 (3)	0.0313 (10)
H6	1.3267	0.5326	0.7515	0.038*
C7	1.1017 (5)	0.3924 (5)	0.6270 (3)	0.0307 (9)
H7	1.1516	0.3457	0.5876	0.037*
C8	0.9213 (5)	0.3461 (4)	0.5845 (3)	0.0237 (8)
C9	0.8135 (5)	0.2371 (4)	0.4825 (3)	0.0271 (9)
H9	0.8635	0.1927	0.4415	0.033*
C10	0.6407 (4)	0.1941 (4)	0.4413 (3)	0.0258 (9)
H10	0.5714	0.1208	0.3724	0.031*
C11	0.5773 (5)	0.4377 (4)	0.6616 (3)	0.0229 (8)
H11A	0.4727	0.4324	0.6076	0.028*
H11B	0.6617	0.5576	0.6931	0.028*
C12	0.5199 (4)	0.3418 (4)	0.7549 (3)	0.0197 (8)
C13	0.5735 (4)	0.4221 (4)	0.8626 (3)	0.0252 (9)
H13	0.6500	0.5406	0.8790	0.030*
C14	0.5190 (4)	0.3350 (4)	0.9471 (3)	0.0253 (9)
H14	0.5578	0.3935	1.0206	0.030*
C15	0.4068 (4)	0.1607 (4)	0.9250 (3)	0.0232 (8)
C16	0.3521 (4)	0.0777 (4)	0.8173 (3)	0.0239 (8)
H16	0.2755	−0.0407	0.8011	0.029*
C17	0.4085 (4)	0.1665 (4)	0.7334 (3)	0.0237 (8)
H17	0.3712	0.1080	0.6601	0.028*
C18	0.3479 (5)	0.0751 (5)	1.0184 (3)	0.0270 (9)
C19	0.1690 (5)	−0.1887 (5)	1.0714 (3)	0.0370 (10)
H19A	0.2584	−0.1398	1.1453	0.044*
H19B	0.1414	−0.3068	1.0539	0.044*
C20	0.0044 (5)	−0.1853 (5)	1.0753 (4)	0.0456 (12)
H20A	−0.0423	−0.2501	1.1326	0.068*
H20B	−0.0844	−0.2352	1.0024	0.068*
H20C	0.0324	−0.0685	1.0936	0.068*
C21	0.2804 (5)	0.1041 (5)	0.3632 (3)	0.0269 (9)
H21A	0.2823	−0.0037	0.3652	0.032*
H21B	0.3224	0.1557	0.2998	0.032*
C22	0.0975 (5)	0.0754 (5)	0.3519 (3)	0.0391 (10)
H22A	0.0162	−0.0012	0.2825	0.059*
H22B	0.0981	0.1832	0.3500	0.059*
H22C	0.0586	0.0254	0.4156	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0218 (13)	0.0322 (15)	0.0244 (15)	0.0129 (12)	0.0033 (11)	−0.0036 (12)
O2	0.0468 (18)	0.0490 (19)	0.0254 (17)	0.0154 (15)	0.0137 (14)	0.0015 (14)
O3	0.0401 (16)	0.0282 (15)	0.0361 (17)	0.0159 (13)	0.0204 (14)	0.0098 (13)
C1	0.0210 (19)	0.0218 (19)	0.027 (2)	0.0093 (16)	0.0110 (17)	0.0061 (17)
C2	0.027 (2)	0.0174 (18)	0.021 (2)	0.0115 (16)	0.0092 (16)	0.0035 (15)
C3	0.025 (2)	0.0211 (19)	0.026 (2)	0.0110 (17)	0.0108 (17)	0.0100 (17)
C4	0.030 (2)	0.022 (2)	0.029 (2)	0.0119 (17)	0.0097 (18)	0.0031 (17)
C5	0.027 (2)	0.024 (2)	0.031 (2)	0.0099 (17)	0.0033 (17)	0.0050 (17)
C6	0.022 (2)	0.033 (2)	0.039 (3)	0.0149 (18)	0.0079 (19)	0.011 (2)
C7	0.032 (2)	0.028 (2)	0.043 (3)	0.0188 (18)	0.019 (2)	0.0093 (19)
C8	0.026 (2)	0.0181 (19)	0.030 (2)	0.0113 (17)	0.0132 (17)	0.0077 (17)
C9	0.031 (2)	0.027 (2)	0.029 (2)	0.0158 (18)	0.0143 (18)	0.0064 (17)
C10	0.028 (2)	0.023 (2)	0.026 (2)	0.0119 (17)	0.0094 (18)	0.0002 (17)
C11	0.026 (2)	0.0215 (19)	0.025 (2)	0.0141 (17)	0.0082 (17)	0.0010 (16)
C12	0.0233 (19)	0.0207 (18)	0.021 (2)	0.0158 (16)	0.0066 (16)	0.0029 (16)
C13	0.024 (2)	0.0217 (19)	0.028 (2)	0.0103 (17)	0.0057 (17)	−0.0023 (17)
C14	0.025 (2)	0.031 (2)	0.021 (2)	0.0153 (18)	0.0041 (17)	−0.0017 (17)
C15	0.0199 (19)	0.025 (2)	0.024 (2)	0.0121 (17)	0.0038 (16)	0.0024 (17)
C16	0.0209 (19)	0.022 (2)	0.023 (2)	0.0071 (16)	0.0046 (16)	−0.0014 (17)
C17	0.0236 (19)	0.0232 (19)	0.022 (2)	0.0110 (16)	0.0031 (16)	−0.0035 (16)
C18	0.027 (2)	0.032 (2)	0.027 (2)	0.0178 (18)	0.0087 (18)	0.0044 (19)
C19	0.046 (3)	0.036 (2)	0.042 (3)	0.023 (2)	0.025 (2)	0.017 (2)
C20	0.045 (3)	0.037 (3)	0.059 (3)	0.019 (2)	0.023 (2)	0.013 (2)
C21	0.030 (2)	0.027 (2)	0.020 (2)	0.0120 (18)	0.0043 (17)	−0.0002 (16)
C22	0.032 (2)	0.039 (2)	0.035 (3)	0.013 (2)	0.0028 (19)	−0.005 (2)

Geometric parameters (Å, º) top

O1—C1	1.372 (4)	C11—H11B	0.990
O1—C21	1.436 (4)	C12—C13	1.378 (5)
O2—C18	1.205 (4)	C12—C17	1.403 (4)
O3—C18	1.355 (4)	C13—C14	1.376 (5)
O3—C19	1.452 (4)	C13—H13	0.950
C1—C2	1.388 (5)	C14—C15	1.397 (5)
C1—C10	1.407 (4)	C14—H14	0.950
C2—C3	1.423 (5)	C15—C16	1.385 (5)
C2—C11	1.512 (4)	C15—C18	1.479 (5)
C3—C4	1.423 (5)	C16—C17	1.381 (5)
C3—C8	1.430 (4)	C16—H16	0.950
C4—C5	1.364 (5)	C17—H17	0.950
C4—H4	0.950	C19—C20	1.500 (5)
C5—C6	1.409 (5)	C19—H19A	0.990
C5—H5	0.950	C19—H19B	0.990
C6—C7	1.367 (5)	C20—H20A	0.980
C6—H6	0.950	C20—H20B	0.980
C7—C8	1.413 (5)	C20—H20C	0.980
C7—H7	0.950	C21—C22	1.499 (5)
C8—C9	1.413 (5)	C21—H21A	0.990
C9—C10	1.357 (5)	C21—H21B	0.990
C9—H9	0.950	C22—H22A	0.980
C10—H10	0.950	C22—H22B	0.980
C11—C12	1.512 (5)	C22—H22C	0.980
C11—H11A	0.990

C1—O1—C21	118.5 (3)	C14—C13—H13	119.2
C18—O3—C19	116.7 (3)	C12—C13—H13	119.2
O1—C1—C2	115.6 (3)	C13—C14—C15	120.1 (3)
O1—C1—C10	122.8 (3)	C13—C14—H14	119.9
C2—C1—C10	121.6 (3)	C15—C14—H14	119.9
C1—C2—C3	118.7 (3)	C16—C15—C14	119.0 (3)
C1—C2—C11	119.9 (3)	C16—C15—C18	123.4 (3)
C3—C2—C11	121.4 (3)	C14—C15—C18	117.6 (3)
C2—C3—C4	122.9 (3)	C17—C16—C15	120.3 (3)
C2—C3—C8	119.9 (3)	C17—C16—H16	119.9
C4—C3—C8	117.2 (3)	C15—C16—H16	119.9
C5—C4—C3	121.3 (4)	C16—C17—C12	120.9 (3)
C5—C4—H4	119.3	C16—C17—H17	119.5
C3—C4—H4	119.3	C12—C17—H17	119.5
C4—C5—C6	121.2 (4)	O2—C18—O3	122.7 (4)
C4—C5—H5	119.4	O2—C18—C15	125.2 (4)
C6—C5—H5	119.4	O3—C18—C15	112.2 (3)
C7—C6—C5	119.2 (4)	O3—C19—C20	110.2 (3)
C7—C6—H6	120.4	O3—C19—H19A	109.6
C5—C6—H6	120.4	C20—C19—H19A	109.6
C6—C7—C8	121.3 (3)	O3—C19—H19B	109.6
C6—C7—H7	119.4	C20—C19—H19B	109.6
C8—C7—H7	119.4	H19A—C19—H19B	108.1
C7—C8—C9	122.0 (3)	C19—C20—H20A	109.5
C7—C8—C3	119.8 (3)	C19—C20—H20B	109.5
C9—C8—C3	118.2 (3)	H20A—C20—H20B	109.5
C10—C9—C8	121.9 (4)	C19—C20—H20C	109.5
C10—C9—H9	119.0	H20A—C20—H20C	109.5
C8—C9—H9	119.0	H20B—C20—H20C	109.5
C9—C10—C1	119.7 (3)	O1—C21—C22	105.7 (3)
C9—C10—H10	120.2	O1—C21—H21A	110.6
C1—C10—H10	120.2	C22—C21—H21A	110.6
C2—C11—C12	113.1 (3)	O1—C21—H21B	110.6
C2—C11—H11A	109.0	C22—C21—H21B	110.6
C12—C11—H11A	109.0	H21A—C21—H21B	108.7
C2—C11—H11B	109.0	C21—C22—H22A	109.5
C12—C11—H11B	109.0	C21—C22—H22B	109.5
H11A—C11—H11B	107.8	H22A—C22—H22B	109.5
C13—C12—C17	117.9 (3)	C21—C22—H22C	109.5
C13—C12—C11	121.7 (3)	H22A—C22—H22C	109.5
C17—C12—C11	120.3 (3)	H22B—C22—H22C	109.5
C14—C13—C12	121.7 (3)

C21—O1—C1—C2	178.7 (3)	O1—C1—C10—C9	−177.7 (3)
C21—O1—C1—C10	−1.6 (5)	C2—C1—C10—C9	2.0 (5)
O1—C1—C2—C3	178.1 (3)	C1—C2—C11—C12	97.1 (4)
C10—C1—C2—C3	−1.7 (5)	C3—C2—C11—C12	−81.8 (4)
O1—C1—C2—C11	−0.8 (5)	C2—C11—C12—C13	125.7 (3)
C10—C1—C2—C11	179.4 (3)	C2—C11—C12—C17	−54.6 (4)
C1—C2—C3—C4	179.6 (3)	C17—C12—C13—C14	−0.7 (5)
C11—C2—C3—C4	−1.5 (5)	C11—C12—C13—C14	179.0 (3)
C1—C2—C3—C8	−0.4 (5)	C12—C13—C14—C15	0.1 (5)
C11—C2—C3—C8	178.4 (3)	C13—C14—C15—C16	0.2 (5)
C2—C3—C4—C5	−178.8 (4)	C13—C14—C15—C18	−177.9 (3)
C8—C3—C4—C5	1.3 (5)	C14—C15—C16—C17	0.2 (5)
C3—C4—C5—C6	−1.7 (5)	C18—C15—C16—C17	178.1 (3)
C4—C5—C6—C7	1.3 (5)	C15—C16—C17—C12	−0.8 (5)
C5—C6—C7—C8	−0.4 (5)	C13—C12—C17—C16	1.0 (5)
C6—C7—C8—C9	177.4 (4)	C11—C12—C17—C16	−178.7 (3)
C6—C7—C8—C3	0.0 (5)	C19—O3—C18—O2	1.7 (5)
C2—C3—C8—C7	179.7 (3)	C19—O3—C18—C15	−177.8 (3)
C4—C3—C8—C7	−0.4 (5)	C16—C15—C18—O2	−177.5 (4)
C2—C3—C8—C9	2.2 (5)	C14—C15—C18—O2	0.5 (5)
C4—C3—C8—C9	−177.9 (3)	C16—C15—C18—O3	2.0 (5)
C7—C8—C9—C10	−179.3 (4)	C14—C15—C18—O3	−180.0 (3)
C3—C8—C9—C10	−1.9 (5)	C18—O3—C19—C20	85.3 (4)
C8—C9—C10—C1	−0.2 (5)	C1—O1—C21—C22	177.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1	0.99	2.33	2.737 (4)	104
C21—H21B···O2ⁱ	0.99	2.57	3.477 (5)	153

Symmetry code: (i) x, y, z−1.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

1-(4-Carboethoxy­phenyl­methyl)-2-ethoxy­naphthalene

Supporting information

Key indicators

checkCIF results

1-(4-Carboethoxyphenylmethyl)-2-ethoxynaphthalene