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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1948.
Published online 2009 July 22. doi:  10.1107/S1600536809027974
PMCID: PMC2977507

3,4,5-Trimeth­oxy-N-(2-methoxy­phen­yl)benzamide

Abstract

In the title mol­ecule, C17H19NO5, the amide plane is oriented at an angle of 41.5 (3)° with respect to the 2-methoxy­benzene ring. The three meth­oxy groups lie almost in the plane of the aromatic rings to which they are attached [C—O—C—C torsion angles of of 0.7 (4), −13.4 (4) and 3.1 (4)°], whereas the meth­oxy group at the 4-position of the 3,4,5-trimethoxy­benzene ring is nearly perpendicularly oriented [C—O—C—C torsion angle of 103.9 (3)°]. In the crystal structure, inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into chains along [001].

Related literature

The background of this work has been described in our earlier paper (Saeed et al. 2008 [triangle]). For a related structure, see: Parra et al. (2001 [triangle]).

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Object name is e-65-o1948-scheme1.jpg

Experimental

Crystal data

  • C17H19NO5
  • M r = 317.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1948-efi1.jpg
  • a = 7.409 (2) Å
  • b = 22.522 (6) Å
  • c = 9.681 (3) Å
  • V = 1615.4 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 120 K
  • 0.50 × 0.44 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.953, T max = 0.981
  • 13253 measured reflections
  • 2050 independent reflections
  • 1902 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.126
  • S = 1.13
  • 2050 reflections
  • 216 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027974/wm2245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027974/wm2245Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

AS gratefully acknowledges a reasearch grant from Quaid-i-Azam University, Islamabad, under the URF project.

supplementary crystallographic information

Comment

The background of this work has been described in our earlier paper (Saeed et al. 2008).

The molecular structure of the title compound (Fig. 1) is similar to that of ICULOH (Parra et al., 2001), but with 3,4,5-methoxy substitution of the benzamide ring. Methoxy groups O2, O3 and O5 lie almost in plane of the corresponding aromatic rings with torsion angles C8–O2–C7–C6 of 0.7 (4)°, C15–O3–C11–C10 of -13.4 (4)° and C17–O5–C13–C14 of 3.1 (4)°, respectively, whereas the O4-group is nearly perpendicular oriented with C16–O4–C12–C13 of 103.9 (3)°. The two aromatic planes make a dihedral angle of 67.66 (9)° and the angle between the amide group and the 2-methoxy benzene ring is 41.5 (3)°. In the cystal structure, intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the [001] direction (Fig. 2).

Experimental

3,4,5-Trimethoxybenzoyl chloride (1 mmol) in CHCl3 was treated with 2-methoxyaniline (3.5 mmol) under a nitrogen atmosphere at reflux conditions for 5 h. Upon cooling, the reaction mixture was diluted with CHCl3 and washed consecutively with 1 M aq HCl and saturated aq NaHCO3. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in methanol afforded the title compound (84%) as white needles: Anal. calc. for C17H19NO5: C 64.34, H 6.03, N 4.41%; found: C 64.31, H 6.09, N 4.34%

Refinement

All H atoms were clearly identified in difference syntheses, then refined at calculated positions riding on the carbon atoms (C–H = 0.95–0.99 Å) with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) or 1.5U(–CH3). All CH3 hydrogen atoms were allowed to rotate but not to tip. H(N) was refined freely with a restained (DFIX) N–H distance. The title compound crystallizes in the non-centrosymmetric space group P ca21; however, in the absence of significant anomalous scattering effects, the Flack parameter is essentially meaningless. Accordingly, Friedel pairs were merged.

Figures

Fig. 1.
Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing viewed along [100] with intermolecular hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

Crystal data

C17H19NO5F(000) = 672
Mr = 317.33Dx = 1.305 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 887 reflections
a = 7.409 (2) Åθ = 2.9–27.6°
b = 22.522 (6) ŵ = 0.10 mm1
c = 9.681 (3) ÅT = 120 K
V = 1615.4 (7) Å3Prism, colourless
Z = 40.50 × 0.44 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer2050 independent reflections
Radiation source: sealed tube1902 reflections with I > 2σ(I)
graphiteRint = 0.047
[var phi] and ω scansθmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −9→9
Tmin = 0.953, Tmax = 0.981k = −29→25
13253 measured reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: difference Fourier map
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.0648P)2 + 0.6933P] where P = (Fo2 + 2Fc2)/3
2050 reflections(Δ/σ)max < 0.001
216 parametersΔρmax = 0.37 e Å3
2 restraintsΔρmin = −0.20 e Å3

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 (Å2)

xyzUiso*/Ueq
O10.1314 (3)0.22502 (9)1.0268 (2)0.0232 (5)
O2−0.0063 (3)0.16331 (10)0.5858 (2)0.0246 (5)
O30.7319 (3)0.33720 (9)0.7087 (2)0.0258 (5)
O40.6652 (3)0.43489 (9)0.8620 (3)0.0246 (5)
O50.4036 (3)0.43643 (9)1.0503 (3)0.0263 (5)
N10.1909 (3)0.19743 (11)0.8055 (3)0.0199 (5)
H10.232 (7)0.2095 (18)0.723 (3)0.053 (13)*
C10.2067 (3)0.23480 (13)0.9166 (3)0.0186 (6)
C20.0968 (3)0.14253 (13)0.8110 (3)0.0189 (6)
C30.1076 (4)0.10537 (14)0.9251 (4)0.0242 (6)
H3A0.18040.11631.00180.029*
C40.0117 (4)0.05177 (14)0.9278 (4)0.0285 (7)
H4A0.01790.02681.00680.034*
C5−0.0923 (4)0.03511 (14)0.8150 (4)0.0294 (7)
H5A−0.1575−0.00120.81690.035*
C6−0.1012 (4)0.07152 (14)0.6989 (4)0.0270 (7)
H6A−0.17180.05980.62170.032*
C7−0.0069 (4)0.12518 (13)0.6956 (3)0.0211 (6)
C8−0.1114 (5)0.14694 (18)0.4675 (4)0.0382 (9)
H8A−0.06810.10890.43120.057*
H8B−0.09960.17760.39610.057*
H8C−0.23850.14320.49420.057*
C90.3260 (4)0.28794 (12)0.8974 (3)0.0167 (5)
C100.4689 (4)0.28683 (13)0.8036 (3)0.0183 (5)
H10A0.48590.25320.74570.022*
C110.5872 (4)0.33511 (13)0.7945 (3)0.0181 (5)
C120.5583 (4)0.38548 (13)0.8771 (3)0.0204 (6)
C130.4143 (4)0.38603 (12)0.9724 (3)0.0194 (6)
C140.2986 (4)0.33723 (12)0.9835 (3)0.0190 (6)
H14A0.20260.33741.04860.023*
C150.7858 (5)0.28235 (14)0.6464 (4)0.0328 (8)
H15A0.79790.25180.71790.049*
H15B0.90190.28770.59950.049*
H15C0.69450.27000.57900.049*
C160.8392 (5)0.42964 (16)0.9272 (5)0.0367 (9)
H16A0.82340.42551.02730.055*
H16B0.91090.46520.90770.055*
H16C0.90180.39460.89110.055*
C170.2685 (5)0.43817 (14)1.1558 (4)0.0323 (7)
H17A0.14870.43521.11350.048*
H17B0.27790.47571.20670.048*
H17C0.28650.40491.21950.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0229 (10)0.0307 (11)0.0159 (10)−0.0039 (8)0.0057 (9)−0.0036 (9)
O20.0247 (11)0.0311 (11)0.0179 (10)−0.0079 (9)−0.0033 (8)−0.0018 (9)
O30.0239 (10)0.0295 (10)0.0242 (12)−0.0046 (9)0.0100 (10)−0.0015 (9)
O40.0241 (10)0.0229 (11)0.0268 (11)−0.0044 (8)0.0023 (9)0.0033 (9)
O50.0285 (11)0.0234 (10)0.0270 (13)−0.0027 (8)0.0081 (10)−0.0053 (9)
N10.0205 (11)0.0271 (12)0.0121 (11)−0.0043 (9)0.0007 (10)−0.0019 (10)
C10.0142 (12)0.0266 (14)0.0150 (13)0.0016 (10)−0.0024 (10)−0.0014 (11)
C20.0150 (12)0.0240 (14)0.0176 (14)0.0001 (10)0.0058 (11)−0.0033 (12)
C30.0207 (14)0.0289 (15)0.0231 (16)0.0044 (11)0.0028 (12)−0.0002 (12)
C40.0266 (15)0.0269 (15)0.0320 (18)0.0057 (12)0.0090 (14)0.0062 (14)
C50.0242 (14)0.0203 (14)0.044 (2)−0.0035 (11)0.0069 (15)−0.0030 (14)
C60.0223 (14)0.0281 (15)0.0307 (18)−0.0025 (12)0.0014 (13)−0.0079 (13)
C70.0180 (13)0.0242 (14)0.0211 (15)0.0006 (11)0.0042 (11)−0.0033 (12)
C80.0381 (19)0.049 (2)0.0276 (18)−0.0158 (16)−0.0144 (16)0.0038 (17)
C90.0160 (12)0.0243 (13)0.0098 (12)−0.0004 (10)−0.0027 (10)−0.0004 (10)
C100.0207 (12)0.0245 (13)0.0098 (12)0.0018 (10)−0.0005 (11)−0.0018 (11)
C110.0163 (11)0.0272 (14)0.0107 (13)0.0006 (10)0.0026 (10)0.0014 (11)
C120.0223 (13)0.0218 (14)0.0171 (14)0.0000 (11)−0.0036 (11)0.0038 (11)
C130.0197 (13)0.0228 (14)0.0156 (14)0.0015 (10)−0.0031 (11)0.0001 (12)
C140.0178 (12)0.0275 (14)0.0118 (12)0.0025 (10)−0.0008 (11)−0.0007 (11)
C150.0301 (17)0.0315 (15)0.0368 (19)−0.0044 (12)0.0173 (16)−0.0034 (16)
C160.0308 (17)0.0338 (19)0.045 (2)−0.0093 (14)−0.0069 (17)0.0000 (16)
C170.0352 (17)0.0316 (15)0.0300 (18)−0.0030 (14)0.0107 (16)−0.0127 (15)

Geometric parameters (Å, °)

O1—C11.224 (4)C6—H6A0.9500
O2—C71.366 (4)C8—H8A0.9800
O2—C81.434 (4)C8—H8B0.9800
O3—C111.357 (3)C8—H8C0.9800
O3—C151.432 (4)C9—C101.395 (4)
O4—C121.374 (4)C9—C141.403 (4)
O4—C161.441 (4)C10—C111.400 (4)
O5—C131.365 (4)C10—H10A0.9500
O5—C171.431 (4)C11—C121.404 (4)
N1—C11.371 (4)C12—C131.410 (4)
N1—C21.420 (4)C13—C141.398 (4)
N1—H10.895 (10)C14—H14A0.9500
C1—C91.500 (4)C15—H15A0.9800
C2—C31.388 (4)C15—H15B0.9800
C2—C71.412 (4)C15—H15C0.9800
C3—C41.401 (5)C16—H16A0.9800
C3—H3A0.9500C16—H16B0.9800
C4—C51.389 (5)C16—H16C0.9800
C4—H4A0.9500C17—H17A0.9800
C5—C61.392 (5)C17—H17B0.9800
C5—H5A0.9500C17—H17C0.9800
C6—C71.396 (4)
C7—O2—C8117.3 (2)C10—C9—C1120.9 (2)
C11—O3—C15116.7 (2)C14—C9—C1118.2 (2)
C12—O4—C16113.8 (3)C9—C10—C11120.1 (3)
C13—O5—C17117.3 (2)C9—C10—H10A119.9
C1—N1—C2123.1 (2)C11—C10—H10A119.9
C1—N1—H1119 (3)O3—C11—C10124.1 (3)
C2—N1—H1118 (3)O3—C11—C12116.2 (2)
O1—C1—N1122.3 (3)C10—C11—C12119.8 (3)
O1—C1—C9121.4 (3)O4—C12—C11120.4 (3)
N1—C1—C9116.3 (2)O4—C12—C13119.9 (3)
C3—C2—C7119.7 (3)C11—C12—C13119.7 (3)
C3—C2—N1121.8 (3)O5—C13—C14125.1 (3)
C7—C2—N1118.6 (3)O5—C13—C12114.4 (2)
C2—C3—C4120.3 (3)C14—C13—C12120.5 (3)
C2—C3—H3A119.8C13—C14—C9119.1 (3)
C4—C3—H3A119.8C13—C14—H14A120.4
C5—C4—C3120.0 (3)C9—C14—H14A120.4
C5—C4—H4A120.0O3—C15—H15A109.5
C3—C4—H4A120.0O3—C15—H15B109.5
C4—C5—C6120.1 (3)H15A—C15—H15B109.5
C4—C5—H5A119.9O3—C15—H15C109.5
C6—C5—H5A119.9H15A—C15—H15C109.5
C5—C6—C7120.3 (3)H15B—C15—H15C109.5
C5—C6—H6A119.8O4—C16—H16A109.5
C7—C6—H6A119.8O4—C16—H16B109.5
O2—C7—C6124.3 (3)H16A—C16—H16B109.5
O2—C7—C2116.1 (2)O4—C16—H16C109.5
C6—C7—C2119.6 (3)H16A—C16—H16C109.5
O2—C8—H8A109.5H16B—C16—H16C109.5
O2—C8—H8B109.5O5—C17—H17A109.5
H8A—C8—H8B109.5O5—C17—H17B109.5
O2—C8—H8C109.5H17A—C17—H17B109.5
H8A—C8—H8C109.5O5—C17—H17C109.5
H8B—C8—H8C109.5H17A—C17—H17C109.5
C10—C9—C14120.7 (3)H17B—C17—H17C109.5
C2—N1—C1—O1−4.4 (4)C1—C9—C10—C11−175.1 (3)
C2—N1—C1—C9174.0 (2)C15—O3—C11—C10−13.4 (4)
C1—N1—C2—C3−39.8 (4)C15—O3—C11—C12167.1 (3)
C1—N1—C2—C7141.6 (3)C9—C10—C11—O3178.4 (3)
C7—C2—C3—C4−2.0 (4)C9—C10—C11—C12−2.0 (4)
N1—C2—C3—C4179.4 (3)C16—O4—C12—C11−78.5 (4)
C2—C3—C4—C51.1 (5)C16—O4—C12—C13103.9 (3)
C3—C4—C5—C60.1 (5)O3—C11—C12—O44.5 (4)
C4—C5—C6—C7−0.5 (5)C10—C11—C12—O4−175.1 (3)
C8—O2—C7—C60.7 (4)O3—C11—C12—C13−177.9 (3)
C8—O2—C7—C2−179.6 (3)C10—C11—C12—C132.5 (4)
C5—C6—C7—O2179.2 (3)C17—O5—C13—C143.1 (4)
C5—C6—C7—C2−0.4 (4)C17—O5—C13—C12−175.6 (3)
C3—C2—C7—O2−178.0 (2)O4—C12—C13—O5−4.6 (4)
N1—C2—C7—O20.6 (4)C11—C12—C13—O5177.7 (3)
C3—C2—C7—C61.7 (4)O4—C12—C13—C14176.6 (3)
N1—C2—C7—C6−179.7 (3)C11—C12—C13—C14−1.1 (4)
O1—C1—C9—C10151.4 (3)O5—C13—C14—C9−179.5 (3)
N1—C1—C9—C10−27.1 (4)C12—C13—C14—C9−0.8 (4)
O1—C1—C9—C14−24.0 (4)C10—C9—C14—C131.3 (4)
N1—C1—C9—C14157.6 (2)C1—C9—C14—C13176.7 (2)
C14—C9—C10—C110.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.90 (1)2.18 (1)3.066 (4)169 (4)

Symmetry codes: (i) −x+1/2, y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2245).

References

  • Bruker (2002). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Parra, R. D., Zeng, H., Zhu, J., Zheng, C., Zeng, X. C. & Gong, B. (2001). Chem. Eur. J.7, 4352–4357. [PubMed]
  • Saeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o1976. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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