organic compounds
N-(3-Bromophenyl)-3,4,5-trimethoxybenzamide
aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str.7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: aamersaeed@yahoo.com
In the title compound, C16H16BrNO4, the dihedral between the planes of the aromatic rings is 7.74 (18)°. The amide group is tilted with respect to the bromo- and methoxy-substituted aromatic rings by 36.3 (8) and 35.2 (8)°, respectively. The meta-methoxy groups are essentially in-plane with the aromatic ring [dihedral angles CH3—O—C—C = −4.6 (4) and −2.5 (4)°]. The para-methoxy group is markedly displaced from the ring plane [dihedral angle CH3—O—C—C = −72.5 (4)°]. The crystal packing is stabilized by N—H⋯O hydrogen bonds linking the molecules into chains running along the b axis.
Related literature
For related structures and general background, see: Saeed et al. (2009). For conformations of aromatic methoxy groups, see: Vande Velde et al. (2006).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2001); cell X-AREA; data reduction: X-AREA; 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.
Supporting information
10.1107/S1600536809020509/zl2213sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020509/zl2213Isup2.hkl
3,4,5-Trimethoxybenzoyl chloride (5.4 mmol) in CHCl3 was treated with 3-bromoaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl3 and washed consecutively with aq 1 M HCl and saturated aq NaHCO3. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl3 afforded the title compound (81%) as colourless needles. Anal. calcd. for C16H16BrNO4: C, 52.48; H, 4.40; N, 3.82%; found: C, 52.51; H, 4.36; N, 3.87
H atoms were located in a difference map but those bonded to C were geometrically positioned and refined using a riding model with fixed individual displacement parameters [U(Hiso) = 1.2Ueq(C) or U(Hiso) = 1.5Ueq(Cmethyl)] using a riding model with Caromatic—H = 0.95 Å or Cmethyl—H = 0.98 Å. The H atom bonded to N was freely refined.
Data collection: X-AREA (Stoe & Cie, 2001); cell
X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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).C16H16BrNO4 | F(000) = 744 |
Mr = 366.21 | Dx = 1.563 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 11796 reflections |
a = 13.3085 (8) Å | θ = 3.5–26.7° |
b = 4.9953 (3) Å | µ = 2.66 mm−1 |
c = 23.4061 (12) Å | T = 173 K |
V = 1556.04 (15) Å3 | Plate, colourless |
Z = 4 | 0.37 × 0.34 × 0.19 mm |
Stoe IPDS II two-circle diffractometer | 3028 independent reflections |
Radiation source: fine-focus sealed tube | 2748 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 26.3°, θmin = 3.5° |
Absorption correction: multi-scan [MULABS (Spek, 2009; Blessing, 1995)] | h = −16→16 |
Tmin = 0.418, Tmax = 0.600 | k = −6→6 |
11994 measured reflections | l = −29→26 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.076 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.46 e Å−3 |
3028 reflections | Δρmin = −0.39 e Å−3 |
207 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0168 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1405 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.001 (8) |
C16H16BrNO4 | V = 1556.04 (15) Å3 |
Mr = 366.21 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 13.3085 (8) Å | µ = 2.66 mm−1 |
b = 4.9953 (3) Å | T = 173 K |
c = 23.4061 (12) Å | 0.37 × 0.34 × 0.19 mm |
Stoe IPDS II two-circle diffractometer | 3028 independent reflections |
Absorption correction: multi-scan [MULABS (Spek, 2009; Blessing, 1995)] | 2748 reflections with I > 2σ(I) |
Tmin = 0.418, Tmax = 0.600 | Rint = 0.056 |
11994 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | Δρmax = 0.46 e Å−3 |
S = 0.99 | Δρmin = −0.39 e Å−3 |
3028 reflections | Absolute structure: Flack (1983), with 1405 Friedel pairs |
207 parameters | Absolute structure parameter: 0.001 (8) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.19897 (2) | 0.79946 (7) | 0.12371 (2) | 0.04356 (13) | |
N1 | 0.52764 (18) | 0.5080 (5) | 0.23414 (11) | 0.0203 (5) | |
H1 | 0.546 (3) | 0.351 (8) | 0.2441 (17) | 0.023 (9)* | |
O1 | 0.51118 (18) | 0.9515 (4) | 0.25246 (10) | 0.0285 (5) | |
O2 | 0.62891 (16) | 0.9862 (4) | 0.46087 (9) | 0.0276 (4) | |
O3 | 0.78413 (15) | 0.6364 (4) | 0.46308 (10) | 0.0259 (4) | |
O4 | 0.82971 (16) | 0.3369 (4) | 0.37342 (10) | 0.0276 (5) | |
C1 | 0.5457 (2) | 0.7303 (5) | 0.26493 (13) | 0.0204 (6) | |
C11 | 0.4666 (2) | 0.4924 (5) | 0.18432 (13) | 0.0220 (6) | |
C12 | 0.3799 (2) | 0.6447 (6) | 0.17818 (13) | 0.0246 (6) | |
H12 | 0.3613 | 0.7724 | 0.2063 | 0.030* | |
C13 | 0.3216 (2) | 0.6057 (6) | 0.13014 (16) | 0.0279 (6) | |
C14 | 0.3467 (3) | 0.4244 (7) | 0.08727 (14) | 0.0334 (7) | |
H14 | 0.3060 | 0.4043 | 0.0542 | 0.040* | |
C15 | 0.4334 (3) | 0.2740 (7) | 0.09471 (15) | 0.0332 (7) | |
H15 | 0.4520 | 0.1466 | 0.0665 | 0.040* | |
C16 | 0.4931 (3) | 0.3066 (6) | 0.14241 (13) | 0.0270 (6) | |
H16 | 0.5523 | 0.2022 | 0.1467 | 0.032* | |
C21 | 0.6099 (2) | 0.6961 (5) | 0.31655 (12) | 0.0201 (5) | |
C22 | 0.5883 (2) | 0.8619 (5) | 0.36327 (13) | 0.0220 (6) | |
H22 | 0.5343 | 0.9859 | 0.3614 | 0.026* | |
C23 | 0.6460 (2) | 0.8435 (5) | 0.41199 (12) | 0.0206 (6) | |
C24 | 0.7280 (2) | 0.6655 (5) | 0.41433 (13) | 0.0210 (6) | |
C25 | 0.7487 (2) | 0.5016 (5) | 0.36721 (13) | 0.0201 (5) | |
C26 | 0.6890 (2) | 0.5141 (5) | 0.31853 (13) | 0.0213 (6) | |
H26 | 0.7021 | 0.3997 | 0.2870 | 0.026* | |
C27 | 0.5500 (2) | 1.1804 (6) | 0.45934 (14) | 0.0279 (6) | |
H27A | 0.5610 | 1.3033 | 0.4273 | 0.042* | |
H27B | 0.5495 | 1.2817 | 0.4952 | 0.042* | |
H27C | 0.4853 | 1.0895 | 0.4545 | 0.042* | |
C28 | 0.8483 (3) | 0.8582 (7) | 0.47549 (15) | 0.0337 (7) | |
H28A | 0.9001 | 0.8727 | 0.4459 | 0.051* | |
H28B | 0.8805 | 0.8308 | 0.5127 | 0.051* | |
H28C | 0.8086 | 1.0232 | 0.4764 | 0.051* | |
C29 | 0.8502 (2) | 0.1607 (6) | 0.32691 (15) | 0.0287 (7) | |
H29A | 0.7910 | 0.0496 | 0.3194 | 0.043* | |
H29B | 0.9074 | 0.0456 | 0.3366 | 0.043* | |
H29C | 0.8664 | 0.2659 | 0.2928 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02770 (15) | 0.0536 (2) | 0.0494 (2) | 0.00300 (13) | −0.0092 (2) | 0.0107 (3) |
N1 | 0.0287 (12) | 0.0138 (10) | 0.0184 (12) | −0.0002 (9) | −0.0028 (10) | −0.0013 (9) |
O1 | 0.0429 (12) | 0.0152 (9) | 0.0273 (11) | 0.0026 (8) | −0.0104 (10) | −0.0011 (8) |
O2 | 0.0303 (11) | 0.0332 (10) | 0.0192 (10) | 0.0084 (8) | −0.0025 (9) | −0.0069 (9) |
O3 | 0.0274 (10) | 0.0289 (10) | 0.0214 (11) | −0.0008 (8) | −0.0053 (8) | 0.0023 (8) |
O4 | 0.0232 (10) | 0.0286 (11) | 0.0311 (12) | 0.0097 (8) | −0.0021 (9) | −0.0039 (9) |
C1 | 0.0237 (13) | 0.0175 (12) | 0.0199 (14) | −0.0026 (9) | 0.0012 (11) | 0.0009 (10) |
C11 | 0.0280 (14) | 0.0206 (11) | 0.0176 (14) | −0.0031 (11) | 0.0002 (11) | 0.0026 (11) |
C12 | 0.0277 (15) | 0.0248 (13) | 0.0212 (14) | −0.0013 (11) | −0.0001 (12) | 0.0019 (11) |
C13 | 0.0250 (12) | 0.0337 (13) | 0.0251 (18) | −0.0052 (10) | 0.0008 (13) | 0.0053 (14) |
C14 | 0.0352 (17) | 0.0428 (17) | 0.0223 (16) | −0.0146 (14) | −0.0052 (13) | 0.0034 (14) |
C15 | 0.0402 (19) | 0.0357 (17) | 0.0235 (17) | −0.0072 (14) | 0.0011 (14) | −0.0058 (13) |
C16 | 0.0326 (16) | 0.0253 (14) | 0.0232 (16) | −0.0008 (12) | 0.0003 (12) | −0.0039 (11) |
C21 | 0.0225 (14) | 0.0169 (11) | 0.0208 (14) | −0.0018 (10) | −0.0025 (10) | 0.0014 (11) |
C22 | 0.0244 (14) | 0.0184 (12) | 0.0232 (15) | 0.0018 (10) | 0.0007 (12) | −0.0005 (10) |
C23 | 0.0242 (14) | 0.0197 (13) | 0.0178 (14) | −0.0015 (10) | 0.0040 (11) | −0.0035 (11) |
C24 | 0.0215 (13) | 0.0229 (13) | 0.0186 (14) | −0.0018 (10) | −0.0016 (11) | 0.0009 (11) |
C25 | 0.0181 (12) | 0.0185 (13) | 0.0238 (15) | −0.0001 (10) | 0.0005 (11) | 0.0021 (10) |
C26 | 0.0243 (14) | 0.0191 (12) | 0.0205 (14) | −0.0010 (10) | 0.0029 (11) | −0.0019 (10) |
C27 | 0.0324 (16) | 0.0244 (14) | 0.0269 (16) | 0.0064 (12) | 0.0015 (13) | −0.0055 (12) |
C28 | 0.0318 (17) | 0.0352 (17) | 0.0341 (19) | −0.0032 (14) | −0.0116 (14) | −0.0036 (14) |
C29 | 0.0296 (16) | 0.0257 (15) | 0.0308 (17) | 0.0070 (12) | 0.0062 (13) | −0.0021 (13) |
Br1—C13 | 1.903 (3) | C15—H15 | 0.9500 |
N1—C1 | 1.346 (4) | C16—H16 | 0.9500 |
N1—C11 | 1.423 (4) | C21—C26 | 1.392 (4) |
N1—H1 | 0.85 (4) | C21—C22 | 1.401 (4) |
O1—C1 | 1.232 (3) | C22—C23 | 1.378 (4) |
O2—C23 | 1.367 (3) | C22—H22 | 0.9500 |
O2—C27 | 1.431 (3) | C23—C24 | 1.409 (4) |
O3—C24 | 1.371 (4) | C24—C25 | 1.401 (4) |
O3—C28 | 1.429 (4) | C25—C26 | 1.391 (4) |
O4—C25 | 1.363 (3) | C26—H26 | 0.9500 |
O4—C29 | 1.426 (4) | C27—H27A | 0.9800 |
C1—C21 | 1.490 (4) | C27—H27B | 0.9800 |
C11—C12 | 1.389 (4) | C27—H27C | 0.9800 |
C11—C16 | 1.396 (4) | C28—H28A | 0.9800 |
C12—C13 | 1.380 (5) | C28—H28B | 0.9800 |
C12—H12 | 0.9500 | C28—H28C | 0.9800 |
C13—C14 | 1.393 (5) | C29—H29A | 0.9800 |
C14—C15 | 1.388 (5) | C29—H29B | 0.9800 |
C14—H14 | 0.9500 | C29—H29C | 0.9800 |
C15—C16 | 1.379 (4) | ||
C1—N1—C11 | 125.9 (2) | C21—C22—H22 | 120.3 |
C1—N1—H1 | 124 (2) | O2—C23—C22 | 124.4 (3) |
C11—N1—H1 | 110 (2) | O2—C23—C24 | 115.2 (2) |
C23—O2—C27 | 117.1 (2) | C22—C23—C24 | 120.4 (3) |
C24—O3—C28 | 114.4 (2) | O3—C24—C25 | 119.1 (3) |
C25—O4—C29 | 116.3 (2) | O3—C24—C23 | 121.4 (2) |
O1—C1—N1 | 123.2 (3) | C25—C24—C23 | 119.4 (3) |
O1—C1—C21 | 120.6 (2) | O4—C25—C26 | 124.5 (3) |
N1—C1—C21 | 116.2 (2) | O4—C25—C24 | 115.1 (3) |
C12—C11—C16 | 120.1 (3) | C26—C25—C24 | 120.4 (2) |
C12—C11—N1 | 121.9 (3) | C25—C26—C21 | 119.3 (3) |
C16—C11—N1 | 117.9 (3) | C25—C26—H26 | 120.4 |
C13—C12—C11 | 118.3 (3) | C21—C26—H26 | 120.4 |
C13—C12—H12 | 120.8 | O2—C27—H27A | 109.5 |
C11—C12—H12 | 120.8 | O2—C27—H27B | 109.5 |
C12—C13—C14 | 122.9 (3) | H27A—C27—H27B | 109.5 |
C12—C13—Br1 | 118.4 (3) | O2—C27—H27C | 109.5 |
C14—C13—Br1 | 118.7 (2) | H27A—C27—H27C | 109.5 |
C15—C14—C13 | 117.5 (3) | H27B—C27—H27C | 109.5 |
C15—C14—H14 | 121.3 | O3—C28—H28A | 109.5 |
C13—C14—H14 | 121.3 | O3—C28—H28B | 109.5 |
C16—C15—C14 | 121.1 (3) | H28A—C28—H28B | 109.5 |
C16—C15—H15 | 119.5 | O3—C28—H28C | 109.5 |
C14—C15—H15 | 119.5 | H28A—C28—H28C | 109.5 |
C15—C16—C11 | 120.1 (3) | H28B—C28—H28C | 109.5 |
C15—C16—H16 | 119.9 | O4—C29—H29A | 109.5 |
C11—C16—H16 | 119.9 | O4—C29—H29B | 109.5 |
C26—C21—C22 | 121.0 (3) | H29A—C29—H29B | 109.5 |
C26—C21—C1 | 122.4 (2) | O4—C29—H29C | 109.5 |
C22—C21—C1 | 116.6 (2) | H29A—C29—H29C | 109.5 |
C23—C22—C21 | 119.5 (3) | H29B—C29—H29C | 109.5 |
C23—C22—H22 | 120.3 | ||
C11—N1—C1—O1 | −0.9 (5) | C27—O2—C23—C22 | −4.6 (4) |
C11—N1—C1—C21 | 178.3 (3) | C27—O2—C23—C24 | 176.5 (2) |
C1—N1—C11—C12 | −35.8 (4) | C21—C22—C23—O2 | −176.9 (3) |
C1—N1—C11—C16 | 147.8 (3) | C21—C22—C23—C24 | 1.9 (4) |
C16—C11—C12—C13 | 0.3 (4) | C28—O3—C24—C25 | 111.7 (3) |
N1—C11—C12—C13 | −176.0 (3) | C28—O3—C24—C23 | −72.5 (4) |
C11—C12—C13—C14 | −1.2 (4) | O2—C23—C24—O3 | 1.4 (4) |
C11—C12—C13—Br1 | 176.5 (2) | C22—C23—C24—O3 | −177.5 (3) |
C12—C13—C14—C15 | 1.5 (5) | O2—C23—C24—C25 | 177.1 (2) |
Br1—C13—C14—C15 | −176.2 (2) | C22—C23—C24—C25 | −1.8 (4) |
C13—C14—C15—C16 | −1.0 (5) | C29—O4—C25—C26 | −2.5 (4) |
C14—C15—C16—C11 | 0.2 (5) | C29—O4—C25—C24 | 177.7 (3) |
C12—C11—C16—C15 | 0.2 (4) | O3—C24—C25—O4 | −4.4 (4) |
N1—C11—C16—C15 | 176.6 (3) | C23—C24—C25—O4 | 179.8 (2) |
O1—C1—C21—C26 | −146.1 (3) | O3—C24—C25—C26 | 175.8 (3) |
N1—C1—C21—C26 | 34.6 (4) | C23—C24—C25—C26 | 0.0 (4) |
O1—C1—C21—C22 | 32.5 (4) | O4—C25—C26—C21 | −178.2 (2) |
N1—C1—C21—C22 | −146.8 (3) | C24—C25—C26—C21 | 1.6 (4) |
C26—C21—C22—C23 | −0.3 (4) | C22—C21—C26—C25 | −1.5 (4) |
C1—C21—C22—C23 | −178.9 (2) | C1—C21—C26—C25 | 177.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.85 (4) | 2.06 (4) | 2.821 (3) | 149 (3) |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H16BrNO4 |
Mr | 366.21 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 173 |
a, b, c (Å) | 13.3085 (8), 4.9953 (3), 23.4061 (12) |
V (Å3) | 1556.04 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.66 |
Crystal size (mm) | 0.37 × 0.34 × 0.19 |
Data collection | |
Diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | Multi-scan [MULABS (Spek, 2009; Blessing, 1995)] |
Tmin, Tmax | 0.418, 0.600 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11994, 3028, 2748 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.076, 0.99 |
No. of reflections | 3028 |
No. of parameters | 207 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.39 |
Absolute structure | Flack (1983), with 1405 Friedel pairs |
Absolute structure parameter | 0.001 (8) |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.85 (4) | 2.06 (4) | 2.821 (3) | 149 (3) |
Symmetry code: (i) x, y−1, z. |
Acknowledgements
AI gratefully acknowledges a research scholarship from the HEC, Islamabad, Pakistan, under the HEC Indigenous PhD Scholarship 5000 Scheme.
References
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The background to this study has been described in an earlier paper on N-(2-chlorophenyl)-4-chlorobenzamide (Saeed et al., 2009). As part of our work on the structure of benzanilides and related compounds, we report here the structure of the title compound, Fig. 1.
In the title compound, C16H16BrNO4, the dihedral angle between the aromatic rings is 7.74 (18)°. The amide moiety is tilted against the bromo and methoxy substituted aromatic rings by 36.3 (8)° and 35.2 (8)°, respectively. The meta methoxy groups are essentially in plane with the aromatic ring [dihedral angles CH3—O—C—C = -4.6 (4)° and -2.5 (4)°], the methoxy group in para position is markedly displaced from the ring plane [dihedral angle CH3—O—C—C = -72.5 (4)°]. This can be attributed to a combination of resonance effects, which lead for aromatic methoxy groups to being coplanar with an aromatic ring, and steric interactions, which prohibit a coplanar arrangement when more than two methoxy groups are present per benzene moiety (Vande Velde et al., 2006). The crystal packing is stabilized by N—H···O hydrogen bonds linking the molecules to chains running along the b axis (Fig. 2).