N-(3-Bromo-phen-yl)-3,4,5-trimethoxy-benzamide.

In the title compound, C(16)H(16)BrNO(4), the dihedral between the planes of the aromatic rings is 7.74 (18)°. The amide group is tilted with respect to the bromo- and meth-oxy-substituted aromatic rings by 36.3 (8) and 35.2 (8)°, respectively. The meta-meth-oxy groups are essentially in-plane with the aromatic ring [dihedral angles CH(3)-O-C-C = -4.6 (4) and -2.5 (4)°]. The para-meth-oxy group is markedly displaced from the ring plane [dihedral angle CH(3)-O-C-C = -72.5 (4)°]. The crystal packing is stabilized by N-H⋯O hydrogen bonds linking the mol-ecules 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

C16H16BrNO4

M = 366.21

Orthorhombic,

a = 13.3085 (8) Å

b = 4.9953 (3) Å

c = 23.4061 (12) Å

V = 1556.04 (15) Å3

Z = 4

Mo Kα radiation

μ = 2.66 mm−1

T = 173 K

0.37 × 0.34 × 0.19 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan [MULABS (Spek, 2009 ▶; Blessing, 1995 ▶)] T min = 0.418, T max = 0.600

11994 measured reflections

3028 independent reflections

2748 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 0.99

3028 reflections

207 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), with 1405 Friedel pairs

Flack parameter: 0.001 (8)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020509/zl2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020509/zl2213Isup2.hkl

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

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	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	Flack parameter: 0.001 (8)

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) .