2,4-Bis(methoxy­meth­yl)-1,3,5-trimethyl­benzene

The title compound, C₁₃H₂₀O₂, displays polar ordering owing to inter­molecular C—H...O hydrogen bonds that link the mol­ecules to form a three-dimensional network. A twofold rotation axis bisects the ring, passing through the unsubstituted C atom, the para-C atom and C of the attached methyl group.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.070
• wR factor = 0.165
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.27
           From the CIF: _reflns_number_total                747
           Count of symmetry unique reflns          789
           Completeness (_total/calc)             94.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour 2001); software used to prepare material for publication: SHELXL97.

2,4-Bis(methoxymethyl)-1,3,5-trimethylbenzene

Crystal data

C13H20O2	F(000) = 912
Mr = 208.29	Dx = 1.166 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 428 reflections
a = 14.253 (16) Å	θ = 3.1–21.0°
b = 20.66 (2) Å	µ = 0.08 mm^−1
c = 8.057 (9) Å	T = 100 K
V = 2373 (4) Å^3	Block, colorless
Z = 8	0.50 × 0.38 × 0.26 mm

Data collection

Bruker APEX CCD area-detector diffractometer	623 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.084
Graphite monochromator	θmax = 28.3°, θmin = 3.1°
ω scans	h = −18→18
3575 measured reflections	k = −26→18
747 independent reflections	l = −8→10

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 6.8504P] where P = (Fo^2 + 2Fc^2)/3
747 reflections	(Δ/σ)max = 0.008
73 parameters	Δρmax = 0.32 e Å^−3
1 restraint	Δρmin = −0.26 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	Occ. (<1)
C1	0.0000	0.0000	0.3928 (7)	0.0186 (14)
C2	−0.0259 (3)	0.0559 (2)	0.4784 (5)	0.0171 (10)
C4	0.0000	0.0000	0.7369 (8)	0.0197 (13)
H4	0.0000	0.0000	0.8548	0.024*
C3	−0.0251 (3)	0.0562 (2)	0.6537 (5)	0.0157 (10)
C6	−0.0499 (3)	0.1156 (2)	0.7539 (6)	0.0243 (11)
H6A	−0.0424	0.1061	0.8724	0.036*
H6B	−0.1151	0.1278	0.7317	0.036*
H6C	−0.0083	0.1513	0.7228	0.036*
C5	0.0000	0.0000	0.2040 (8)	0.0237 (14)
H5A	0.0488	−0.0294	0.1634	0.035*	0.50
H5B	0.0125	0.0439	0.1634	0.035*	0.50
H5C	−0.0613	−0.0145	0.1634	0.035*	0.50
C7	−0.0547 (3)	0.1158 (2)	0.3846 (6)	0.0206 (10)
H7A	−0.0992	0.1039	0.2953	0.025*
H7B	−0.0866	0.1462	0.4607	0.025*
O8	0.02628 (18)	0.14630 (14)	0.3139 (5)	0.0225 (7)
C9	−0.0004 (3)	0.2019 (2)	0.2229 (7)	0.0279 (11)
H9A	−0.0440	0.1894	0.1345	0.042*
H9B	0.0555	0.2219	0.1738	0.042*
H9C	−0.0310	0.2329	0.2972	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.011 (3)	0.034 (4)	0.011 (3)	−0.011 (3)	0.000	0.000
C2	0.013 (2)	0.022 (2)	0.016 (2)	−0.0034 (17)	0.0037 (17)	0.0035 (17)
C4	0.014 (3)	0.030 (4)	0.016 (3)	0.004 (3)	0.000	0.000
C3	0.0081 (19)	0.022 (2)	0.017 (2)	−0.0028 (17)	0.0029 (15)	0.0008 (17)
C6	0.021 (2)	0.028 (3)	0.024 (2)	0.001 (2)	0.0044 (19)	−0.006 (2)
C5	0.026 (3)	0.028 (4)	0.016 (3)	0.006 (3)	0.000	0.000
C7	0.018 (2)	0.021 (2)	0.023 (2)	−0.0002 (19)	0.0030 (18)	0.0006 (18)
O8	0.0183 (13)	0.0213 (17)	0.0280 (17)	0.0001 (11)	0.0002 (14)	0.0122 (16)
C9	0.026 (2)	0.026 (3)	0.032 (3)	0.004 (2)	0.004 (2)	0.009 (2)

Geometric parameters (Å, º)

C1—C2	1.394 (5)	C5—H5A	0.9800
C1—C5	1.521 (8)	C5—H5B	0.9800
C2—C3	1.412 (5)	C5—H5C	0.9800
C2—C7	1.507 (6)	C7—O8	1.433 (5)
C4—C3	1.387 (5)	C7—H7A	0.9900
C4—H4	0.9500	C7—H7B	0.9900
C3—C6	1.511 (6)	O8—C9	1.415 (5)
C6—H6A	0.9800	C9—H9A	0.9800
C6—H6B	0.9800	C9—H9B	0.9800
C6—H6C	0.9800	C9—H9C	0.9800
C2—C1—C2^i	120.7 (5)	C1—C5—H5B	109.5
C2—C1—C5	119.6 (3)	H5A—C5—H5B	109.5
C2^i—C1—C5	119.6 (3)	C1—C5—H5C	109.5
C1—C2—C3	119.7 (4)	H5A—C5—H5C	109.5
C1—C2—C7	120.2 (4)	H5B—C5—H5C	109.5
C3—C2—C7	120.0 (4)	O8—C7—C2	110.0 (4)
C3^i—C4—C3	122.2 (6)	O8—C7—H7A	109.7
C3^i—C4—H4	118.9	C2—C7—H7A	109.7
C3—C4—H4	118.9	O8—C7—H7B	109.7
C4—C3—C2	118.8 (4)	C2—C7—H7B	109.7
C4—C3—C6	118.8 (4)	H7A—C7—H7B	108.2
C2—C3—C6	122.4 (4)	C9—O8—C7	110.3 (3)
C3—C6—H6A	109.5	O8—C9—H9A	109.5
C3—C6—H6B	109.5	O8—C9—H9B	109.5
H6A—C6—H6B	109.5	H9A—C9—H9B	109.5
C3—C6—H6C	109.5	O8—C9—H9C	109.5
H6A—C6—H6C	109.5	H9A—C9—H9C	109.5
H6B—C6—H6C	109.5	H9B—C9—H9C	109.5
C1—C5—H5A	109.5
C2^i—C1—C2—C3	0.6 (3)	C7—C2—C3—C4	178.8 (3)
C5—C1—C2—C3	−179.4 (3)	C1—C2—C3—C6	178.4 (3)
C2^i—C1—C2—C7	−179.4 (4)	C7—C2—C3—C6	−1.6 (6)
C5—C1—C2—C7	0.6 (4)	C1—C2—C7—O8	−74.5 (4)
C3^i—C4—C3—C2	0.6 (3)	C3—C2—C7—O8	105.5 (5)
C3^i—C4—C3—C6	−179.0 (4)	C2—C7—O8—C9	178.9 (4)
C1—C2—C3—C4	−1.2 (6)

Symmetry code: (i) −x, −y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O8	0.98	2.45	3.172 (5)	131
C7—H7A···O8^ii	0.98	2.57	3.542 (7)	166

Symmetry code: (ii) x−1/4, −y+1/4, z−1/4.