3,4,5-Trimeth­oxy-1-methyl­benzene

The asymmetric unit of the title compound, C₁₀H₁₄O₃, comprises two independent mol­ecules. All bond lengths and angles are within normal ranges.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.146
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

   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

   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Coenzyme Q₀ is the simplest ubiquinone that has no isoprenyl side chain. Its importance lies in the use of synthesizing other coenzyme Q compounds, especially coenzyme Q₁₀ which plays a central role in the two important biological electron-transfer reactions–respiration and photosynthesis. 3,4,5-trimethoxy-methylbenzene is the intermediate in the synthesis of Coenzyme Qo. We report here the structure of the title compound, (I), Fig 1. The bond lengths and angles of the title compound agree with those in the related compound 2,3,4-Trimethoxy-6-methylbenzaldehyde (Zhang et al., 2005) as representative example. (Table 1).

Related literature

For related literature, see: Cheng et al. (2004); Zhang et al. (2005).

S2. Experimental

The compound was obtained as Colourless block crystals using the tecnique described by Cheng et al., 2004.

S3. Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5 U_eq(methyl C).

Computing details

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

Figures

Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.

3,4,5-Trimethoxy-1-methylbenzene

Crystal data

C10H14O3	F(000) = 784
Mr = 182.21	Dx = 1.204 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2724 reflections
a = 13.902 (11) Å	θ = 2.8–22.5°
b = 8.123 (7) Å	µ = 0.09 mm^−1
c = 18.021 (14) Å	T = 294 K
β = 98.883 (14)°	Block, colourless
V = 2011 (3) Å^3	0.26 × 0.24 × 0.22 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	3556 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→16
Tmin = 0.978, Tmax = 0.981	k = −9→9
10097 measured reflections	l = −21→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0655P)^2 + 0.3999P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
3556 reflections	Δρmax = 0.16 e Å^−3
243 parameters	Δρmin = −0.15 e Å^−3
12 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0160 (19)

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	0.02646 (13)	0.7944 (2)	0.93359 (11)	0.0811 (6)
O2	0.17759 (12)	0.6040 (2)	0.98496 (9)	0.0737 (5)
O3	0.35210 (14)	0.6563 (2)	0.94730 (11)	0.0850 (6)
O4	0.31318 (13)	0.2503 (2)	0.08410 (9)	0.0780 (5)
O5	0.37108 (12)	0.37561 (18)	0.22006 (9)	0.0646 (5)
O6	0.47742 (12)	0.20326 (19)	0.32750 (9)	0.0687 (5)
C1	0.2257 (3)	1.1155 (4)	0.78266 (19)	0.1166 (12)
H1A	0.2632	1.0745	0.7462	0.175*
H1B	0.2590	1.2069	0.8089	0.175*
H1C	0.1630	1.1509	0.7578	0.175*
C2	0.2127 (2)	0.9804 (3)	0.83815 (13)	0.0715 (7)
C3	0.12352 (19)	0.9533 (3)	0.85913 (13)	0.0666 (7)
H3	0.0706	1.0181	0.8393	0.080*
C4	0.11210 (18)	0.8303 (3)	0.90965 (13)	0.0603 (6)
C5	0.19031 (18)	0.7328 (3)	0.93873 (12)	0.0565 (6)
C6	0.27995 (19)	0.7610 (3)	0.91703 (13)	0.0612 (6)
C7	0.2911 (2)	0.8853 (3)	0.86754 (13)	0.0687 (7)
H7	0.3519	0.9053	0.8539	0.082*
C8	−0.0564 (2)	0.8845 (4)	0.90251 (19)	0.1051 (11)
H8A	−0.0490	0.9972	0.9184	0.158*
H8B	−0.1130	0.8386	0.9192	0.158*
H8C	−0.0639	0.8793	0.8487	0.158*
C9	0.2051 (2)	0.6352 (4)	1.06233 (15)	0.0933 (9)
H9A	0.2725	0.6660	1.0720	0.140*
H9B	0.1953	0.5377	1.0904	0.140*
H9C	0.1660	0.7230	1.0773	0.140*
C10	0.4437 (2)	0.6752 (5)	0.9263 (2)	0.1088 (11)
H10A	0.4389	0.6599	0.8730	0.163*
H10B	0.4875	0.5950	0.9519	0.163*
H10C	0.4678	0.7838	0.9394	0.163*
C11	0.4870 (2)	−0.2676 (3)	0.15599 (17)	0.0894 (9)
H11A	0.5209	−0.3176	0.2008	0.134*
H11B	0.5295	−0.2618	0.1188	0.134*
H11C	0.4309	−0.3326	0.1371	0.134*
C12	0.45528 (17)	−0.0966 (3)	0.17368 (14)	0.0625 (6)
C13	0.39781 (17)	−0.0057 (3)	0.11903 (14)	0.0640 (7)
H13	0.3789	−0.0504	0.0715	0.077*
C14	0.36843 (16)	0.1505 (3)	0.13461 (13)	0.0564 (6)
C15	0.39629 (15)	0.2174 (3)	0.20540 (12)	0.0505 (6)
C16	0.45387 (15)	0.1268 (3)	0.25996 (12)	0.0517 (6)
C17	0.48328 (16)	−0.0301 (3)	0.24381 (14)	0.0601 (6)
H17	0.5222	−0.0910	0.2806	0.072*
C18	0.2924 (2)	0.1991 (4)	0.00807 (15)	0.0917 (9)
H18A	0.3522	0.1777	−0.0106	0.138*
H18B	0.2571	0.2844	−0.0214	0.138*
H18C	0.2538	0.1007	0.0047	0.138*
C19	0.2803 (2)	0.3894 (3)	0.24503 (16)	0.0835 (8)
H19A	0.2306	0.3419	0.2084	0.125*
H19B	0.2658	0.5035	0.2519	0.125*
H19C	0.2825	0.3322	0.2919	0.125*
C20	0.5391 (2)	0.1175 (4)	0.38557 (15)	0.0885 (9)
H20A	0.5069	0.0195	0.3985	0.133*
H20B	0.5531	0.1870	0.4290	0.133*
H20C	0.5987	0.0883	0.3682	0.133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0687 (12)	0.0801 (12)	0.0936 (14)	−0.0031 (10)	0.0094 (10)	0.0109 (10)
O2	0.0848 (12)	0.0626 (11)	0.0695 (11)	−0.0120 (9)	−0.0015 (9)	0.0113 (9)
O3	0.0781 (13)	0.0901 (14)	0.0876 (13)	0.0125 (10)	0.0148 (10)	0.0178 (11)
O4	0.0978 (13)	0.0760 (12)	0.0544 (10)	0.0159 (10)	−0.0066 (9)	0.0013 (9)
O5	0.0778 (11)	0.0439 (9)	0.0709 (11)	0.0034 (8)	0.0079 (9)	0.0009 (8)
O6	0.0840 (12)	0.0566 (10)	0.0592 (10)	0.0067 (8)	−0.0086 (8)	−0.0028 (8)
C1	0.135 (3)	0.114 (3)	0.104 (2)	0.009 (2)	0.029 (2)	0.054 (2)
C2	0.096 (2)	0.0670 (17)	0.0517 (15)	−0.0009 (15)	0.0120 (14)	0.0062 (13)
C3	0.0778 (18)	0.0611 (16)	0.0579 (15)	0.0044 (13)	0.0011 (13)	0.0029 (13)
C4	0.0671 (16)	0.0553 (15)	0.0562 (15)	−0.0058 (12)	0.0022 (12)	−0.0048 (12)
C5	0.0702 (16)	0.0484 (14)	0.0486 (13)	−0.0057 (12)	0.0013 (12)	0.0026 (11)
C6	0.0721 (17)	0.0634 (16)	0.0466 (13)	0.0052 (13)	0.0041 (12)	−0.0010 (12)
C7	0.0826 (18)	0.0694 (17)	0.0569 (15)	−0.0006 (14)	0.0200 (13)	0.0000 (13)
C8	0.0640 (18)	0.116 (3)	0.132 (3)	0.0141 (17)	0.0053 (18)	0.012 (2)
C9	0.118 (2)	0.101 (2)	0.0594 (18)	−0.0078 (18)	0.0089 (16)	0.0130 (16)
C10	0.083 (2)	0.133 (3)	0.115 (3)	0.0250 (19)	0.0279 (19)	0.019 (2)
C11	0.102 (2)	0.0650 (18)	0.101 (2)	0.0152 (15)	0.0164 (17)	−0.0127 (16)
C12	0.0645 (15)	0.0518 (14)	0.0724 (17)	0.0016 (12)	0.0145 (13)	−0.0049 (13)
C13	0.0726 (16)	0.0616 (16)	0.0577 (15)	−0.0027 (13)	0.0095 (12)	−0.0094 (12)
C14	0.0584 (14)	0.0546 (15)	0.0553 (14)	0.0004 (11)	0.0056 (11)	0.0039 (12)
C15	0.0543 (13)	0.0408 (13)	0.0572 (14)	−0.0029 (10)	0.0106 (11)	0.0022 (11)
C16	0.0538 (13)	0.0475 (13)	0.0532 (14)	−0.0044 (10)	0.0067 (11)	−0.0002 (11)
C17	0.0586 (14)	0.0528 (15)	0.0682 (16)	0.0034 (11)	0.0082 (12)	0.0068 (12)
C18	0.102 (2)	0.111 (2)	0.0554 (16)	0.0090 (18)	−0.0089 (15)	−0.0018 (16)
C19	0.090 (2)	0.0728 (18)	0.090 (2)	0.0231 (15)	0.0200 (16)	−0.0050 (16)
C20	0.109 (2)	0.0823 (19)	0.0639 (17)	0.0138 (17)	−0.0203 (15)	0.0012 (15)

Geometric parameters (Å, º)

O1—C4	1.359 (3)	C9—H9A	0.9600
O1—C8	1.407 (3)	C9—H9B	0.9600
O2—C5	1.366 (3)	C9—H9C	0.9600
O2—C9	1.411 (3)	C10—H10A	0.9600
O3—C6	1.363 (3)	C10—H10B	0.9600
O3—C10	1.392 (4)	C10—H10C	0.9600
O4—C14	1.364 (3)	C11—C12	1.507 (4)
O4—C18	1.418 (3)	C11—H11A	0.9600
O5—C15	1.368 (3)	C11—H11B	0.9600
O5—C19	1.409 (3)	C11—H11C	0.9600
O6—C16	1.361 (3)	C12—C17	1.374 (3)
O6—C20	1.428 (3)	C12—C13	1.382 (3)
C1—C2	1.514 (4)	C13—C14	1.375 (3)
C1—H1A	0.9600	C13—H13	0.9300
C1—H1B	0.9600	C14—C15	1.386 (3)
C1—H1C	0.9600	C15—C16	1.381 (3)
C2—C3	1.368 (4)	C16—C17	1.383 (3)
C2—C7	1.374 (4)	C17—H17	0.9300
C3—C4	1.378 (3)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.381 (3)	C18—H18C	0.9600
C5—C6	1.382 (3)	C19—H19A	0.9600
C6—C7	1.372 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—H8A	0.9600	C20—H20A	0.9600
C8—H8B	0.9600	C20—H20B	0.9600
C8—H8C	0.9600	C20—H20C	0.9600
C4—O1—C8	117.8 (2)	O3—C10—H10C	109.5
C5—O2—C9	115.1 (2)	H10A—C10—H10C	109.5
C6—O3—C10	118.0 (2)	H10B—C10—H10C	109.5
C14—O4—C18	118.7 (2)	C12—C11—H11A	109.5
C15—O5—C19	113.90 (18)	C12—C11—H11B	109.5
C16—O6—C20	117.85 (19)	H11A—C11—H11B	109.5
C2—C1—H1A	109.5	C12—C11—H11C	109.5
C2—C1—H1B	109.5	H11A—C11—H11C	109.5
H1A—C1—H1B	109.5	H11B—C11—H11C	109.5
C2—C1—H1C	109.5	C17—C12—C13	119.8 (2)
H1A—C1—H1C	109.5	C17—C12—C11	120.4 (2)
H1B—C1—H1C	109.5	C13—C12—C11	119.8 (2)
C3—C2—C7	120.1 (2)	C14—C13—C12	120.3 (2)
C3—C2—C1	120.3 (3)	C14—C13—H13	119.9
C7—C2—C1	119.6 (3)	C12—C13—H13	119.9
C2—C3—C4	120.1 (2)	O4—C14—C13	124.5 (2)
C2—C3—H3	120.0	O4—C14—C15	115.4 (2)
C4—C3—H3	120.0	C13—C14—C15	120.0 (2)
O1—C4—C3	124.2 (2)	O5—C15—C16	120.0 (2)
O1—C4—C5	115.7 (2)	O5—C15—C14	120.2 (2)
C3—C4—C5	120.2 (2)	C16—C15—C14	119.7 (2)
O2—C5—C4	120.1 (2)	O6—C16—C15	115.2 (2)
O2—C5—C6	120.5 (2)	O6—C16—C17	124.8 (2)
C4—C5—C6	119.3 (2)	C15—C16—C17	119.9 (2)
O3—C6—C7	124.7 (2)	C12—C17—C16	120.3 (2)
O3—C6—C5	115.1 (2)	C12—C17—H17	119.9
C7—C6—C5	120.2 (2)	C16—C17—H17	119.9
C6—C7—C2	120.1 (2)	O4—C18—H18A	109.5
C6—C7—H7	119.9	O4—C18—H18B	109.5
C2—C7—H7	119.9	H18A—C18—H18B	109.5
O1—C8—H8A	109.5	O4—C18—H18C	109.5
O1—C8—H8B	109.5	H18A—C18—H18C	109.5
H8A—C8—H8B	109.5	H18B—C18—H18C	109.5
O1—C8—H8C	109.5	O5—C19—H19A	109.5
H8A—C8—H8C	109.5	O5—C19—H19B	109.5
H8B—C8—H8C	109.5	H19A—C19—H19B	109.5
O2—C9—H9A	109.5	O5—C19—H19C	109.5
O2—C9—H9B	109.5	H19A—C19—H19C	109.5
H9A—C9—H9B	109.5	H19B—C19—H19C	109.5
O2—C9—H9C	109.5	O6—C20—H20A	109.5
H9A—C9—H9C	109.5	O6—C20—H20B	109.5
H9B—C9—H9C	109.5	H20A—C20—H20B	109.5
O3—C10—H10A	109.5	O6—C20—H20C	109.5
O3—C10—H10B	109.5	H20A—C20—H20C	109.5
H10A—C10—H10B	109.5	H20B—C20—H20C	109.5
C7—C2—C3—C4	−0.2 (4)	C17—C12—C13—C14	−0.1 (4)
C1—C2—C3—C4	−180.0 (2)	C11—C12—C13—C14	180.0 (2)
C8—O1—C4—C3	2.6 (4)	C18—O4—C14—C13	−7.0 (4)
C8—O1—C4—C5	−176.7 (2)	C18—O4—C14—C15	172.0 (2)
C2—C3—C4—O1	−179.9 (2)	C12—C13—C14—O4	178.8 (2)
C2—C3—C4—C5	−0.6 (4)	C12—C13—C14—C15	−0.1 (4)
C9—O2—C5—C4	−100.0 (3)	C19—O5—C15—C16	−94.5 (2)
C9—O2—C5—C6	83.9 (3)	C19—O5—C15—C14	88.9 (3)
O1—C4—C5—O2	3.6 (3)	O4—C14—C15—O5	−2.2 (3)
C3—C4—C5—O2	−175.7 (2)	C13—C14—C15—O5	176.9 (2)
O1—C4—C5—C6	179.8 (2)	O4—C14—C15—C16	−178.81 (19)
C3—C4—C5—C6	0.5 (3)	C13—C14—C15—C16	0.2 (3)
C10—O3—C6—C7	−0.6 (4)	C20—O6—C16—C15	−178.3 (2)
C10—O3—C6—C5	178.4 (2)	C20—O6—C16—C17	1.7 (3)
O2—C5—C6—O3	−2.4 (3)	O5—C15—C16—O6	3.2 (3)
C4—C5—C6—O3	−178.6 (2)	C14—C15—C16—O6	179.90 (19)
O2—C5—C6—C7	176.6 (2)	O5—C15—C16—C17	−176.78 (19)
C4—C5—C6—C7	0.5 (3)	C14—C15—C16—C17	−0.1 (3)
O3—C6—C7—C2	177.6 (2)	C13—C12—C17—C16	0.3 (3)
C5—C6—C7—C2	−1.3 (4)	C11—C12—C17—C16	−179.9 (2)
C3—C2—C7—C6	1.1 (4)	O6—C16—C17—C12	179.8 (2)
C1—C2—C7—C6	−179.1 (2)	C15—C16—C17—C12	−0.1 (3)