2-(4-Methyl­phen­yl)-2-oxoethyl 3,4-di­meth­oxy­benzoate

In the title compound, C₁₈H₁₈O₅, the dihedral angle between the mean planes of the two aromatic rings is 66.55 (8)°. The crystal packing features by inter­molecular C—H...O contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.169
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5854
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.585         48 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          43 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate

Crystal data

C18H18O5	Z = 2
Mr = 314.32	F(000) = 332
Triclinic, P1	Dx = 1.364 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.9805 (3) Å	Cell parameters from 2522 reflections
b = 8.6087 (3) Å	θ = 5.2–64.5°
c = 11.4674 (4) Å	µ = 0.82 mm^−1
α = 99.678 (2)°	T = 293 K
β = 99.173 (2)°	Block, light yellow
γ = 91.495 (2)°	0.30 × 0.25 × 0.20 mm
V = 765.55 (5) Å^3

Data collection

Bruker X8 Proteum diffractometer	2053 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.055
Graphite monochromator	θmax = 64.5°, θmin = 5.2°
Detector resolution: 18.4 pixels mm^-1	h = −9→9
φ and ω scans	k = −10→9
10314 measured reflections	l = −13→13
2522 independent reflections

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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.169	w = 1/[σ^2(Fo^2) + (0.121P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2522 reflections	Δρmax = 0.30 e Å^−3
212 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: shelxl, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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
O9	−0.09184 (18)	0.75607 (14)	0.67623 (13)	0.0300 (5)
O11	0.19147 (17)	0.78179 (14)	0.83817 (13)	0.0261 (5)
O13	0.08365 (17)	0.82775 (14)	1.00977 (13)	0.0288 (5)
O20	0.42611 (16)	0.24229 (13)	0.82041 (12)	0.0234 (4)
O22	0.39935 (16)	0.15667 (14)	1.02101 (12)	0.0228 (4)
C1	−0.2712 (3)	1.3978 (3)	0.4619 (2)	0.0363 (7)
C2	−0.2107 (2)	1.2678 (2)	0.52842 (18)	0.0251 (6)
C3	−0.0852 (2)	1.2978 (2)	0.62938 (18)	0.0246 (6)
C4	−0.0257 (2)	1.1782 (2)	0.68962 (18)	0.0230 (6)
C5	−0.0911 (2)	1.0230 (2)	0.64858 (17)	0.0204 (6)
C6	−0.2189 (2)	0.9924 (2)	0.54882 (19)	0.0252 (6)
C7	−0.2772 (2)	1.1132 (2)	0.48971 (19)	0.0262 (6)
C8	−0.0261 (2)	0.8887 (2)	0.70705 (17)	0.0218 (6)
C10	0.1250 (2)	0.9248 (2)	0.80637 (19)	0.0246 (6)
C12	0.1576 (2)	0.7440 (2)	0.94225 (18)	0.0222 (6)
C14	0.2227 (2)	0.5891 (2)	0.96242 (18)	0.0210 (6)
C15	0.2037 (2)	0.5396 (2)	1.06763 (19)	0.0225 (6)
C16	0.2605 (2)	0.3952 (2)	1.09167 (18)	0.0211 (6)
C17	0.3360 (2)	0.29900 (19)	1.00736 (18)	0.0198 (6)
C18	0.3534 (2)	0.34750 (19)	0.89866 (18)	0.0189 (6)
C19	0.2971 (2)	0.4923 (2)	0.87634 (18)	0.0197 (6)
C21	0.4526 (3)	0.2905 (2)	0.71130 (18)	0.0257 (6)
C23	0.3883 (3)	0.1034 (2)	1.13133 (19)	0.0263 (6)
H3	−0.04010	1.40040	0.65730	0.0300*
H4	0.05780	1.20130	0.75740	0.0280*
H6	−0.26570	0.89020	0.52160	0.0300*
H7	−0.36240	1.09050	0.42290	0.0310*
H10A	0.21260	0.98460	0.78040	0.0300*
H10B	0.09130	0.98870	0.87600	0.0300*
H17	0.15210	0.60370	1.12370	0.0270*
H19	0.30870	0.52490	0.80460	0.0240*
H22	0.24800	0.36330	1.16350	0.0250*
H25A	0.44430	0.18050	1.19730	0.0390*
H25B	0.44210	0.00500	1.13200	0.0390*
H25C	0.27090	0.08890	1.13870	0.0390*
H28A	0.34490	0.30480	0.66470	0.0380*
H28B	0.51060	0.21090	0.66650	0.0380*
H28C	0.52010	0.38810	0.72930	0.0380*
H99A	−0.24360	1.49800	0.51370	0.0540*
H99B	−0.39200	1.38420	0.43670	0.0540*
H99C	−0.21640	1.39410	0.39290	0.0540*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O9	0.0366 (9)	0.0196 (7)	0.0341 (9)	−0.0002 (5)	0.0066 (7)	0.0049 (6)
O11	0.0334 (8)	0.0210 (7)	0.0272 (9)	0.0128 (5)	0.0084 (6)	0.0090 (6)
O13	0.0348 (8)	0.0227 (7)	0.0329 (9)	0.0118 (6)	0.0152 (7)	0.0055 (6)
O20	0.0313 (8)	0.0185 (7)	0.0220 (8)	0.0066 (5)	0.0096 (6)	0.0021 (5)
O22	0.0286 (8)	0.0167 (6)	0.0258 (8)	0.0085 (5)	0.0077 (6)	0.0069 (5)
C1	0.0465 (14)	0.0344 (11)	0.0317 (13)	0.0144 (9)	0.0075 (11)	0.0134 (9)
C2	0.0264 (11)	0.0285 (10)	0.0241 (12)	0.0107 (8)	0.0109 (9)	0.0077 (8)
C3	0.0286 (11)	0.0205 (9)	0.0265 (12)	0.0043 (7)	0.0080 (9)	0.0057 (8)
C4	0.0225 (10)	0.0242 (9)	0.0228 (11)	0.0036 (7)	0.0032 (8)	0.0059 (8)
C5	0.0220 (10)	0.0218 (10)	0.0194 (11)	0.0042 (7)	0.0090 (8)	0.0039 (7)
C6	0.0261 (10)	0.0243 (10)	0.0239 (12)	0.0017 (7)	0.0040 (9)	0.0010 (8)
C7	0.0269 (11)	0.0318 (10)	0.0190 (11)	0.0072 (8)	0.0028 (8)	0.0024 (8)
C8	0.0259 (10)	0.0197 (9)	0.0224 (11)	0.0051 (7)	0.0106 (9)	0.0040 (8)
C10	0.0282 (11)	0.0178 (9)	0.0296 (12)	0.0070 (7)	0.0047 (9)	0.0082 (8)
C12	0.0182 (10)	0.0204 (9)	0.0276 (12)	0.0013 (7)	0.0027 (9)	0.0040 (8)
C14	0.0165 (10)	0.0171 (9)	0.0287 (12)	0.0033 (7)	0.0029 (8)	0.0029 (8)
C15	0.0204 (10)	0.0195 (9)	0.0288 (12)	0.0052 (7)	0.0089 (9)	0.0027 (8)
C16	0.0208 (10)	0.0216 (9)	0.0214 (11)	0.0017 (7)	0.0041 (8)	0.0047 (8)
C17	0.0163 (9)	0.0161 (9)	0.0266 (12)	0.0019 (7)	0.0023 (8)	0.0039 (8)
C18	0.0175 (9)	0.0158 (9)	0.0226 (11)	0.0033 (7)	0.0045 (8)	−0.0007 (7)
C19	0.0179 (9)	0.0187 (9)	0.0225 (11)	0.0006 (7)	0.0026 (8)	0.0042 (8)
C21	0.0327 (11)	0.0246 (9)	0.0208 (11)	0.0038 (8)	0.0088 (9)	0.0027 (8)
C23	0.0346 (11)	0.0220 (9)	0.0257 (12)	0.0083 (8)	0.0085 (9)	0.0093 (8)

Geometric parameters (Å, º)

O9—C8	1.216 (2)	C16—C17	1.388 (3)
O11—C10	1.433 (2)	C17—C18	1.405 (3)
O11—C12	1.354 (2)	C18—C19	1.386 (2)
O13—C12	1.203 (2)	C1—H99A	0.9600
O20—C18	1.372 (2)	C1—H99B	0.9600
O20—C21	1.427 (2)	C1—H99C	0.9600
O22—C17	1.361 (2)	C3—H3	0.9300
O22—C23	1.431 (2)	C4—H4	0.9300
C1—C2	1.505 (3)	C6—H6	0.9300
C2—C3	1.388 (3)	C7—H7	0.9300
C2—C7	1.393 (3)	C10—H10A	0.9700
C3—C4	1.387 (3)	C10—H10B	0.9700
C4—C5	1.398 (2)	C15—H17	0.9300
C5—C6	1.390 (3)	C16—H22	0.9300
C5—C8	1.496 (3)	C19—H19	0.9300
C6—C7	1.385 (3)	C21—H28A	0.9600
C8—C10	1.507 (3)	C21—H28B	0.9600
C12—C14	1.484 (2)	C21—H28C	0.9600
C14—C15	1.374 (3)	C23—H25A	0.9600
C14—C19	1.399 (3)	C23—H25B	0.9600
C15—C16	1.390 (2)	C23—H25C	0.9600
C10—O11—C12	116.65 (14)	H99A—C1—H99B	110.00
C18—O20—C21	116.91 (14)	H99A—C1—H99C	109.00
C17—O22—C23	117.24 (15)	H99B—C1—H99C	109.00
C1—C2—C3	121.05 (17)	C2—C3—H3	119.00
C1—C2—C7	121.07 (18)	C4—C3—H3	119.00
C3—C2—C7	117.87 (17)	C3—C4—H4	120.00
C2—C3—C4	121.50 (17)	C5—C4—H4	120.00
C3—C4—C5	120.11 (17)	C5—C6—H6	120.00
C4—C5—C6	118.75 (16)	C7—C6—H6	120.00
C4—C5—C8	122.23 (16)	C2—C7—H7	119.00
C6—C5—C8	119.01 (16)	C6—C7—H7	119.00
C5—C6—C7	120.44 (17)	O11—C10—H10A	110.00
C2—C7—C6	121.30 (18)	O11—C10—H10B	110.00
O9—C8—C5	121.72 (16)	C8—C10—H10A	110.00
O9—C8—C10	121.22 (16)	C8—C10—H10B	110.00
C5—C8—C10	117.06 (15)	H10A—C10—H10B	108.00
O11—C10—C8	110.52 (15)	C14—C15—H17	120.00
O11—C12—O13	123.23 (16)	C16—C15—H17	119.00
O11—C12—C14	112.10 (15)	C15—C16—H22	120.00
O13—C12—C14	124.67 (18)	C17—C16—H22	120.00
C12—C14—C15	118.14 (16)	C14—C19—H19	120.00
C12—C14—C19	121.80 (17)	C18—C19—H19	120.00
C15—C14—C19	120.04 (16)	O20—C21—H28A	109.00
C14—C15—C16	121.05 (17)	O20—C21—H28B	109.00
C15—C16—C17	119.34 (18)	O20—C21—H28C	109.00
O22—C17—C16	125.00 (17)	H28A—C21—H28B	109.00
O22—C17—C18	115.00 (16)	H28A—C21—H28C	109.00
C16—C17—C18	119.99 (16)	H28B—C21—H28C	110.00
O20—C18—C17	115.38 (15)	O22—C23—H25A	109.00
O20—C18—C19	124.65 (17)	O22—C23—H25B	109.00
C17—C18—C19	119.97 (17)	O22—C23—H25C	109.00
C14—C19—C18	119.59 (18)	H25A—C23—H25B	110.00
C2—C1—H99A	109.00	H25A—C23—H25C	109.00
C2—C1—H99B	109.00	H25B—C23—H25C	109.00
C2—C1—H99C	109.00
C12—O11—C10—C8	−105.06 (18)	C5—C6—C7—C2	−0.3 (3)
C10—O11—C12—O13	−3.9 (3)	O9—C8—C10—O11	10.7 (2)
C10—O11—C12—C14	176.33 (14)	C5—C8—C10—O11	−169.40 (15)
C21—O20—C18—C17	−177.34 (16)	O11—C12—C14—C15	177.09 (16)
C21—O20—C18—C19	3.3 (2)	O11—C12—C14—C19	−4.8 (2)
C23—O22—C17—C16	−0.6 (3)	O13—C12—C14—C15	−2.7 (3)
C23—O22—C17—C18	178.63 (16)	O13—C12—C14—C19	175.41 (17)
C1—C2—C3—C4	−178.44 (18)	C12—C14—C15—C16	179.44 (16)
C7—C2—C3—C4	0.7 (3)	C19—C14—C15—C16	1.3 (3)
C1—C2—C7—C6	178.34 (18)	C12—C14—C19—C18	−178.94 (16)
C3—C2—C7—C6	−0.8 (3)	C15—C14—C19—C18	−0.9 (3)
C2—C3—C4—C5	0.5 (3)	C14—C15—C16—C17	−0.7 (3)
C3—C4—C5—C6	−1.6 (3)	C15—C16—C17—O22	178.78 (16)
C3—C4—C5—C8	177.30 (16)	C15—C16—C17—C18	−0.4 (3)
C4—C5—C6—C7	1.5 (3)	O22—C17—C18—O20	2.2 (2)
C8—C5—C6—C7	−177.43 (16)	O22—C17—C18—C19	−178.44 (15)
C4—C5—C8—O9	174.62 (17)	C16—C17—C18—O20	−178.56 (15)
C4—C5—C8—C10	−5.3 (2)	C16—C17—C18—C19	0.8 (3)
C6—C5—C8—O9	−6.5 (3)	O20—C18—C19—C14	179.13 (16)
C6—C5—C8—C10	173.57 (16)	C17—C18—C19—C14	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O13	0.97	2.24	2.671 (2)	106
C10—H10B···O13^i	0.97	2.48	3.399 (2)	157
C19—H19···O11	0.93	2.42	2.733 (2)	100
C23—H25B···O20^ii	0.96	2.50	3.447 (2)	168
C23—H25B···O22^ii	0.96	2.57	3.281 (2)	131

Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y, −z+2.