1,3-Bis(3,5-dimethyl­phen­oxy)propane

The mol­ecular structure of the title compound, C₁₉H₂₄O₂, exhibits great similarity to that of the previously published non-derivatized mol­ecule, the greatest difference being seen in the central torsion angles and ring orientations. The structure additionally features a π–π stacking inter­action and a weak C—H...π inter­action.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.050
• wR factor = 0.135
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

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Computing details

Data collection: locally modified CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS96 (Sheldrick, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1,3-Bis(3,5-dimethylphenoxy)propane

Crystal data

C19H24O2	Z = 2
Mr = 284.38	F(000) = 308
Triclinic, P1	Dx = 1.173 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7906 (12) Å	Cell parameters from 25 reflections
b = 9.6774 (11) Å	θ = 10.0–15.2°
c = 10.7788 (12) Å	µ = 0.07 mm^−1
α = 82.410 (9)°	T = 150 K
β = 78.47 (1)°	Block, colourless
γ = 63.796 (9)°	0.5 × 0.5 × 0.4 mm
V = 805.11 (17) Å^3

Data collection

Nonius CAD-4-Turbo diffractometer	Rint = 0.042
Radiation source: rotating anode	θmax = 27.5°, θmin = 1.9°
Graphite monochromator	h = −11→11
ω scans	k = −12→12
4628 measured reflections	l = −13→9
3689 independent reflections	3 standard reflections every 60 min
2710 reflections with I > 2σ(I)	intensity decay: 0.8%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.2118P] where P = (Fo^2 + 2Fc^2)/3
3689 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.19858 (13)	0.02041 (12)	0.91197 (10)	0.0287 (3)
O2	0.04772 (14)	0.41513 (12)	0.73596 (10)	0.0320 (3)
C1	0.30321 (19)	−0.04965 (17)	1.00155 (14)	0.0246 (3)
C2	0.42726 (19)	−0.19888 (17)	0.97723 (14)	0.0255 (3)
H2	0.4338	−0.2449	0.9026	0.031*
C3	0.54117 (19)	−0.28063 (17)	1.06089 (15)	0.0266 (3)
C4	0.5280 (2)	−0.21185 (18)	1.17084 (15)	0.0287 (3)
H4	0.6040	−0.2681	1.2298	0.034*
C5	0.4059 (2)	−0.06269 (18)	1.19565 (14)	0.0279 (3)
C6	0.29291 (19)	0.01874 (17)	1.11031 (14)	0.0269 (3)
H6	0.2089	0.1209	1.1264	0.032*
C7	0.6803 (2)	−0.43945 (19)	1.03229 (17)	0.0356 (4)
H7A	0.6311	−0.5014	1.0049	0.053*
H7B	0.7310	−0.4889	1.1087	0.053*
H7C	0.7693	−0.4314	0.9647	0.053*
C8	0.3998 (2)	0.0136 (2)	1.31095 (16)	0.0387 (4)
H8A	0.4458	−0.0655	1.3775	0.058*
H8B	0.2806	0.0834	1.3419	0.058*
H8C	0.4689	0.0723	1.2885	0.058*
C9	0.05704 (19)	0.16787 (17)	0.93759 (15)	0.0285 (3)
H9A	0.0990	0.2438	0.9502	0.034*
H9B	−0.0215	0.1598	1.0151	0.034*
C10	−0.0346 (2)	0.21699 (18)	0.82409 (15)	0.0299 (4)
H10A	−0.1488	0.3032	0.8468	0.036*
H10B	−0.0529	0.1299	0.8020	0.036*
C11	0.0623 (2)	0.26739 (17)	0.70952 (15)	0.0282 (3)
H11A	0.1844	0.1919	0.6953	0.034*
H11B	0.0119	0.2762	0.6329	0.034*
C12	0.12381 (19)	0.48791 (17)	0.64584 (14)	0.0252 (3)
C13	0.0988 (2)	0.63290 (17)	0.67551 (15)	0.0281 (3)
H13	0.0308	0.6744	0.7536	0.034*
C14	0.1715 (2)	0.71714 (18)	0.59289 (15)	0.0285 (3)
C15	0.2703 (2)	0.65450 (19)	0.47850 (15)	0.0297 (4)
H15	0.3213	0.7113	0.4210	0.036*
C16	0.29532 (19)	0.51033 (18)	0.44736 (14)	0.0277 (3)
C17	0.22140 (19)	0.42651 (17)	0.53162 (14)	0.0267 (3)
H17	0.2377	0.3279	0.5110	0.032*
C18	0.3986 (2)	0.4442 (2)	0.32291 (15)	0.0370 (4)
H18A	0.4434	0.5156	0.2753	0.056*
H18B	0.3253	0.4289	0.2737	0.056*
H18C	0.4945	0.3450	0.3386	0.056*
C19	0.1443 (3)	0.8738 (2)	0.62706 (18)	0.0407 (4)
H19A	0.0221	0.9444	0.6337	0.061*
H19B	0.2108	0.9140	0.5612	0.061*
H19C	0.1823	0.8644	0.7085	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0297 (6)	0.0226 (5)	0.0301 (6)	−0.0071 (5)	−0.0030 (5)	−0.0066 (4)
O2	0.0376 (6)	0.0251 (6)	0.0317 (6)	−0.0141 (5)	0.0039 (5)	−0.0077 (5)
C1	0.0254 (7)	0.0237 (7)	0.0260 (7)	−0.0135 (6)	0.0009 (6)	−0.0027 (6)
C2	0.0289 (8)	0.0241 (7)	0.0249 (7)	−0.0142 (6)	0.0026 (6)	−0.0065 (6)
C3	0.0277 (8)	0.0248 (8)	0.0284 (8)	−0.0138 (6)	0.0004 (6)	−0.0023 (6)
C4	0.0317 (8)	0.0296 (8)	0.0280 (8)	−0.0169 (7)	−0.0027 (6)	−0.0010 (6)
C5	0.0333 (8)	0.0303 (8)	0.0252 (8)	−0.0202 (7)	0.0026 (6)	−0.0053 (6)
C6	0.0285 (8)	0.0220 (7)	0.0296 (8)	−0.0124 (6)	0.0040 (6)	−0.0063 (6)
C7	0.0361 (9)	0.0273 (8)	0.0391 (9)	−0.0081 (7)	−0.0067 (7)	−0.0057 (7)
C8	0.0477 (10)	0.0404 (10)	0.0328 (9)	−0.0225 (9)	−0.0029 (8)	−0.0099 (8)
C9	0.0269 (8)	0.0219 (8)	0.0337 (8)	−0.0097 (6)	0.0028 (6)	−0.0055 (6)
C10	0.0254 (8)	0.0234 (8)	0.0398 (9)	−0.0099 (6)	−0.0020 (7)	−0.0050 (6)
C11	0.0275 (8)	0.0229 (8)	0.0336 (8)	−0.0090 (6)	−0.0045 (6)	−0.0063 (6)
C12	0.0229 (7)	0.0241 (7)	0.0266 (7)	−0.0077 (6)	−0.0055 (6)	−0.0009 (6)
C13	0.0284 (8)	0.0245 (8)	0.0268 (8)	−0.0064 (6)	−0.0027 (6)	−0.0071 (6)
C14	0.0305 (8)	0.0248 (8)	0.0305 (8)	−0.0100 (6)	−0.0088 (6)	−0.0032 (6)
C15	0.0315 (8)	0.0309 (8)	0.0288 (8)	−0.0150 (7)	−0.0059 (6)	−0.0001 (6)
C16	0.0257 (8)	0.0300 (8)	0.0246 (8)	−0.0077 (7)	−0.0063 (6)	−0.0040 (6)
C17	0.0266 (8)	0.0224 (7)	0.0288 (8)	−0.0065 (6)	−0.0066 (6)	−0.0051 (6)
C18	0.0402 (10)	0.0377 (10)	0.0277 (8)	−0.0124 (8)	−0.0006 (7)	−0.0069 (7)
C19	0.0535 (11)	0.0299 (9)	0.0411 (10)	−0.0199 (8)	−0.0041 (8)	−0.0072 (7)

Geometric parameters (Å, º)

O1—C1	1.3673 (18)	C9—H9B	0.9900
O1—C9	1.4351 (18)	C10—C11	1.509 (2)
O2—C12	1.3647 (18)	C10—H10A	0.9900
O2—C11	1.4397 (18)	C10—H10B	0.9900
C1—C6	1.389 (2)	C11—H11A	0.9900
C1—C2	1.392 (2)	C11—H11B	0.9900
C2—C3	1.384 (2)	C12—C17	1.388 (2)
C2—H2	0.9500	C12—C13	1.392 (2)
C3—C4	1.395 (2)	C13—C14	1.381 (2)
C3—C7	1.506 (2)	C13—H13	0.9500
C4—C5	1.388 (2)	C14—C15	1.395 (2)
C4—H4	0.9500	C14—C19	1.511 (2)
C5—C6	1.392 (2)	C15—C16	1.390 (2)
C5—C8	1.507 (2)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.393 (2)
C7—H7A	0.9800	C16—C18	1.503 (2)
C7—H7B	0.9800	C17—H17	0.9500
C7—H7C	0.9800	C18—H18A	0.9800
C8—H8A	0.9800	C18—H18B	0.9800
C8—H8B	0.9800	C18—H18C	0.9800
C8—H8C	0.9800	C19—H19A	0.9800
C9—C10	1.508 (2)	C19—H19B	0.9800
C9—H9A	0.9900	C19—H19C	0.9800
C1—O1—C9	118.14 (12)	C11—C10—H10A	108.9
C12—O2—C11	118.34 (12)	C9—C10—H10B	108.9
O1—C1—C6	124.40 (13)	C11—C10—H10B	108.9
O1—C1—C2	115.44 (13)	H10A—C10—H10B	107.8
C6—C1—C2	120.16 (14)	O2—C11—C10	106.36 (12)
C3—C2—C1	120.51 (14)	O2—C11—H11A	110.5
C3—C2—H2	119.7	C10—C11—H11A	110.5
C1—C2—H2	119.7	O2—C11—H11B	110.5
C2—C3—C4	118.89 (14)	C10—C11—H11B	110.5
C2—C3—C7	120.70 (14)	H11A—C11—H11B	108.6
C4—C3—C7	120.38 (15)	O2—C12—C17	124.51 (14)
C5—C4—C3	121.16 (15)	O2—C12—C13	115.29 (13)
C5—C4—H4	119.4	C17—C12—C13	120.19 (14)
C3—C4—H4	119.4	C14—C13—C12	120.81 (14)
C4—C5—C6	119.38 (14)	C14—C13—H13	119.6
C4—C5—C8	120.61 (15)	C12—C13—H13	119.6
C6—C5—C8	119.96 (15)	C13—C14—C15	118.76 (14)
C1—C6—C5	119.88 (14)	C13—C14—C19	120.14 (14)
C1—C6—H6	120.1	C15—C14—C19	121.09 (15)
C5—C6—H6	120.1	C16—C15—C14	120.98 (15)
C3—C7—H7A	109.5	C16—C15—H15	119.5
C3—C7—H7B	109.5	C14—C15—H15	119.5
H7A—C7—H7B	109.5	C15—C16—C17	119.66 (14)
C3—C7—H7C	109.5	C15—C16—C18	121.03 (15)
H7A—C7—H7C	109.5	C17—C16—C18	119.30 (14)
H7B—C7—H7C	109.5	C12—C17—C16	119.58 (14)
C5—C8—H8A	109.5	C12—C17—H17	120.2
C5—C8—H8B	109.5	C16—C17—H17	120.2
H8A—C8—H8B	109.5	C16—C18—H18A	109.5
C5—C8—H8C	109.5	C16—C18—H18B	109.5
H8A—C8—H8C	109.5	H18A—C18—H18B	109.5
H8B—C8—H8C	109.5	C16—C18—H18C	109.5
O1—C9—C10	106.66 (12)	H18A—C18—H18C	109.5
O1—C9—H9A	110.4	H18B—C18—H18C	109.5
C10—C9—H9A	110.4	C14—C19—H19A	109.5
O1—C9—H9B	110.4	C14—C19—H19B	109.5
C10—C9—H9B	110.4	H19A—C19—H19B	109.5
H9A—C9—H9B	108.6	C14—C19—H19C	109.5
C9—C10—C11	113.18 (13)	H19A—C19—H19C	109.5
C9—C10—H10A	108.9	H19B—C19—H19C	109.5
C9—O1—C1—C6	−6.9 (2)	C12—O2—C11—C10	−179.40 (13)
C9—O1—C1—C2	173.70 (13)	C9—C10—C11—O2	−72.70 (16)
O1—C1—C2—C3	179.52 (13)	C11—O2—C12—C17	−2.9 (2)
C6—C1—C2—C3	0.1 (2)	C11—O2—C12—C13	177.51 (13)
C1—C2—C3—C4	0.9 (2)	O2—C12—C13—C14	178.98 (14)
C1—C2—C3—C7	−177.39 (14)	C17—C12—C13—C14	−0.6 (2)
C2—C3—C4—C5	−1.5 (2)	C12—C13—C14—C15	0.3 (2)
C7—C3—C4—C5	176.82 (14)	C12—C13—C14—C19	−179.47 (15)
C3—C4—C5—C6	1.0 (2)	C13—C14—C15—C16	0.2 (2)
C3—C4—C5—C8	−176.44 (14)	C19—C14—C15—C16	179.92 (15)
O1—C1—C6—C5	−179.93 (13)	C14—C15—C16—C17	−0.3 (2)
C2—C1—C6—C5	−0.6 (2)	C14—C15—C16—C18	178.66 (15)
C4—C5—C6—C1	0.0 (2)	O2—C12—C17—C16	−179.02 (14)
C8—C5—C6—C1	177.50 (14)	C13—C12—C17—C16	0.5 (2)
C1—O1—C9—C10	179.91 (12)	C15—C16—C17—C12	−0.1 (2)
O1—C9—C10—C11	−73.50 (15)	C18—C16—C17—C12	−179.06 (14)