7-Methoxy-4,6-di­methyl-3H-isobenzo­furan-1-one

The title compound, C₁₁H₁₂O₃, exists as a nearly planar mol­ecule, the dihedral angle between the five- and six-membered rings being 1.9 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.060
• wR factor = 0.156
• Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total                897
         Count of symmetry unique reflns          898
         Completeness (_total/calc)             99.89%
         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
          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.

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

7-Methoxy-4,6-dimethyl-3H-isobenzofuran-1-one

Crystal data

C11H12O3	Dx = 1.324 Mg m^−3
Mr = 192.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 1595 reflections
a = 7.5508 (7) Å	θ = 2.6–21.8°
b = 12.616 (1) Å	µ = 0.10 mm^−1
c = 10.1223 (9) Å	T = 298 K
V = 964.27 (15) Å^3	Needle, colorless
Z = 4	0.45 × 0.12 × 0.09 mm
F(000) = 408

Data collection

Bruker APEX area-detector diffractometer	840 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
φ and ω scans	h = −8→8
12924 measured reflections	k = −15→14
897 independent reflections	l = −11→12

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)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.1111P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
897 reflections	Δρmax = 0.15 e Å^−3
129 parameters	Δρmin = −0.26 e Å^−3
1 restraint	Absolute structure: Calculation of Flack parameter suppressed by MERG 4
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3423 (5)	0.9901 (2)	0.4999 (4)	0.067 (1)
O2	0.2527 (5)	0.9312 (3)	0.3053 (4)	0.069 (1)
O3	0.2614 (4)	0.6788 (2)	0.3127 (4)	0.055 (1)
C1	0.3061 (6)	0.9115 (4)	0.4148 (5)	0.052 (1)
C2	0.3997 (8)	0.9475 (4)	0.6241 (5)	0.060 (1)
C3	0.3990 (5)	0.8311 (3)	0.6058 (4)	0.040 (1)
C4	0.4399 (5)	0.7506 (4)	0.6960 (5)	0.041 (1)
C5	0.4198 (6)	0.6486 (4)	0.6492 (4)	0.043 (1)
C6	0.3643 (5)	0.6247 (3)	0.5223 (4)	0.042 (1)
C7	0.3257 (6)	0.7049 (4)	0.4340 (5)	0.043 (1)
C8	0.3440 (6)	0.8101 (3)	0.4787 (5)	0.044 (1)
C9	0.4964 (7)	0.7760 (4)	0.8333 (5)	0.056 (1)
C10	0.3463 (7)	0.5103 (3)	0.4784 (6)	0.059 (1)
C11	0.3633 (8)	0.7076 (5)	0.2007 (6)	0.068 (2)
H2a	0.3194	0.9679	0.6944	0.072*
H2b	0.5177	0.9724	0.6457	0.072*
H5	0.4450	0.5927	0.7061	0.051*
H9a	0.3940	0.7906	0.8865	0.084*
H9b	0.5723	0.8371	0.8323	0.084*
H9C	0.5595	0.7168	0.8698	0.084*
H10a	0.2270	0.4975	0.4498	0.088*
H10b	0.3742	0.4642	0.5509	0.088*
H10c	0.4264	0.4969	0.4067	0.088*
H11a	0.3037	0.6848	0.1219	0.102*
H11b	0.4775	0.6743	0.2057	0.102*
H11c	0.3778	0.7832	0.1987	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.101 (3)	0.038 (2)	0.062 (2)	0.005 (2)	0.003 (2)	0.007 (2)
O2	0.089 (3)	0.062 (2)	0.056 (2)	0.014 (2)	−0.001 (2)	0.023 (2)
O3	0.062 (2)	0.063 (2)	0.042 (2)	−0.011 (2)	−0.004 (2)	−0.002 (2)
C1	0.056 (3)	0.048 (3)	0.052 (3)	0.004 (2)	0.008 (2)	0.011 (2)
C2	0.077 (3)	0.050 (3)	0.052 (3)	−0.002 (2)	0.005 (2)	−0.007 (2)
C3	0.043 (2)	0.038 (2)	0.040 (2)	0.000 (2)	0.005 (2)	−0.005 (2)
C4	0.038 (2)	0.047 (2)	0.038 (2)	0.002 (2)	0.009 (2)	0.003 (2)
C5	0.045 (2)	0.047 (3)	0.036 (2)	0.005 (2)	0.002 (2)	0.014 (2)
C6	0.044 (2)	0.038 (2)	0.043 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C7	0.043 (2)	0.053 (3)	0.034 (2)	−0.002 (2)	0.001 (2)	0.001 (2)
C8	0.047 (2)	0.043 (2)	0.042 (3)	−0.001 (2)	0.004 (2)	0.006 (2)
C9	0.069 (3)	0.058 (3)	0.042 (3)	0.001 (2)	−0.004 (2)	0.001 (2)
C10	0.080 (3)	0.043 (2)	0.054 (3)	−0.005 (2)	−0.001 (3)	−0.003 (2)
C11	0.083 (4)	0.083 (4)	0.039 (3)	−0.006 (3)	0.003 (3)	−0.003 (3)

Geometric parameters (Å, º)

O1—C1	1.342 (6)	C7—C8	1.409 (6)
O1—C2	1.434 (7)	C2—H2a	0.97
O2—C1	1.205 (6)	C2—H2b	0.97
O3—C7	1.361 (6)	C5—H5	0.93
O3—C11	1.418 (7)	C9—H9a	0.96
C1—C8	1.462 (6)	C9—H9b	0.96
C2—C3	1.480 (7)	C9—H9C	0.96
C3—C8	1.377 (7)	C10—H10a	0.96
C3—C4	1.400 (7)	C10—H10b	0.96
C4—C5	1.381 (7)	C10—H10c	0.96
C4—C9	1.489 (7)	C11—H11a	0.96
C5—C6	1.385 (6)	C11—H11b	0.96
C6—C7	1.381 (6)	C11—H11c	0.96
C6—C10	1.515 (6)
C1—O1—C2	110.3 (4)	O1—C2—H2b	110.7
C7—O3—C11	117.7 (3)	C3—C2—H2b	110.7
O2—C1—O1	120.4 (5)	H2a—C2—H2b	108.8
O2—C1—C8	130.7 (5)	C4—C5—H5	118.1
O1—C1—C8	108.8 (4)	C6—C5—H5	118.1
O1—C2—C3	105.2 (4)	C4—C9—H9a	109.5
C8—C3—C4	122.4 (4)	C4—C9—H9b	109.5
C8—C3—C2	108.0 (4)	H9a—C9—H9b	109.5
C4—C3—C2	129.6 (5)	C4—C9—H9C	109.5
C5—C4—C3	115.3 (4)	H9a—C9—H9C	109.5
C5—C4—C9	123.6 (5)	H9b—C9—H9C	109.5
C3—C4—C9	121.1 (4)	C6—C10—H10a	109.5
C4—C5—C6	123.7 (4)	C6—C10—H10b	109.5
C7—C6—C5	120.3 (4)	H10a—C10—H10b	109.5
C7—C6—C10	119.3 (4)	C6—C10—H10c	109.5
C5—C6—C10	120.4 (4)	H10a—C10—H10c	109.5
O3—C7—C6	118.8 (4)	H10b—C10—H10c	109.5
O3—C7—C8	123.5 (4)	O3—C11—H11a	109.5
C6—C7—C8	117.5 (4)	O3—C11—H11b	109.5
C3—C8—C7	120.7 (4)	H11a—C11—H11b	109.5
C3—C8—C1	107.7 (4)	O3—C11—H11c	109.5
C7—C8—C1	131.5 (4)	H11a—C11—H11c	109.5
O1—C2—H2a	110.7	H11b—C11—H11c	109.5
C3—C2—H2a	110.7
C2—O1—C1—O2	178.7 (5)	C10—C6—C7—O3	4.3 (6)
C2—O1—C1—C8	−1.8 (5)	C5—C6—C7—C8	−0.4 (6)
C1—O1—C2—C3	1.2 (5)	C10—C6—C7—C8	180.0 (4)
O1—C2—C3—C8	−0.1 (5)	C4—C3—C8—C7	0.3 (6)
O1—C2—C3—C4	−178.5 (4)	C2—C3—C8—C7	−178.2 (4)
C8—C3—C4—C5	−0.5 (6)	C4—C3—C8—C1	177.6 (4)
C2—C3—C4—C5	177.6 (4)	C2—C3—C8—C1	−0.9 (5)
C8—C3—C4—C9	−179.1 (4)	O3—C7—C8—C3	175.7 (4)
C2—C3—C4—C9	−0.9 (7)	C6—C7—C8—C3	0.2 (6)
C3—C4—C5—C6	0.3 (6)	O3—C7—C8—C1	−0.9 (8)
C9—C4—C5—C6	178.8 (4)	C6—C7—C8—C1	−176.4 (5)
C4—C5—C6—C7	0.1 (6)	O2—C1—C8—C3	−178.9 (5)
C4—C5—C6—C10	179.8 (4)	O1—C1—C8—C3	1.7 (5)
C11—O3—C7—C6	−118.2 (5)	O2—C1—C8—C7	−1.9 (9)
C11—O3—C7—C8	66.4 (6)	O1—C1—C8—C7	178.6 (4)
C5—C6—C7—O3	−176.1 (4)