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

In the title compound, C(16)H(16)BrNO(4), the dihedral angle between the two aromatic rings is 67.51 (25)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds involving the N-H and C=O groups of the amide function, leading to a chain along [-101].

Related literature

For the synthesis and biological activity of 3,4,5-trimeth­oxy­benzamide derivatives, see: Buettner et al. (2009 ▶); Pellicani et al. (2012 ▶). For related structures, see: Saeed & Flörke (2009 ▶); Saeed et al. (2008 ▶); Choi et al. (2010 ▶).

Experimental

Crystal data

C16H16BrNO4

M = 366.21

Monoclinic,

a = 9.5860 (19) Å

b = 26.010 (5) Å

c = 7.1390 (14) Å

β = 112.04 (3)°

V = 1649.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.51 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.634, T max = 0.788

3194 measured reflections

1616 independent reflections

1206 reflections with I > 2σ(I)

R int = 0.064

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.094

S = 1.00

1616 reflections

199 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 91 Friedel pairs

Flack parameter: 0.010 (17)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018946/kp2410sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018946/kp2410Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018946/kp2410Isup3.cml

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

C16H16BrNO4	F(000) = 744
Mr = 366.21	Dx = 1.474 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 25 reflections
a = 9.5860 (19) Å	θ = 10–13°
b = 26.010 (5) Å	µ = 2.51 mm−1
c = 7.1390 (14) Å	T = 293 K
β = 112.04 (3)°	Block, colourless
V = 1649.9 (6) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1206 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −31→31
Tmin = 0.634, Tmax = 0.788	l = −8→7
3194 measured reflections	3 standard reflections every 200 reflections
1616 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.043P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1616 reflections	Δρmax = 0.37 e Å−3
199 parameters	Δρmin = −0.26 e Å−3
2 restraints	Absolute structure: Flack (1983), 91 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.010 (17)

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
Br	0.49808 (11)	0.47594 (3)	0.04427 (12)	0.0691 (3)
N	0.5036 (10)	0.28535 (15)	0.5367 (13)	0.0464 (12)
H0A	0.5729	0.2840	0.6555	0.056*
O1	0.4265 (6)	0.05888 (17)	0.6046 (7)	0.0626 (14)
C6	0.5016 (7)	0.2076 (3)	0.8251 (10)	0.0440 (17)
H6A	0.5203	0.2407	0.8776	0.053*
C5	0.5285 (8)	0.1651 (3)	0.9537 (11)	0.0429 (17)
O2	0.5191 (7)	0.07461 (17)	0.9997 (8)	0.0588 (15)
O3	0.5812 (7)	0.1688 (2)	1.1618 (7)	0.0637 (15)
C4	0.5010 (8)	0.1162 (3)	0.8755 (10)	0.0479 (18)
O4	0.3061 (5)	0.24199 (18)	0.3087 (8)	0.0559 (13)
C3	0.4450 (8)	0.1084 (3)	0.6641 (11)	0.0485 (18)
C2	0.4170 (8)	0.1506 (3)	0.5388 (11)	0.0473 (17)
H2A	0.3778	0.1461	0.3994	0.057*
C1	0.4467 (7)	0.1996 (2)	0.6193 (10)	0.0364 (15)
C7	0.3625 (12)	0.0497 (3)	0.3925 (12)	0.077 (3)
H7A	0.3546	0.0134	0.3677	0.115*
H7B	0.4256	0.0647	0.3297	0.115*
H7C	0.2642	0.0650	0.3372	0.115*
C8	0.6627 (12)	0.0518 (4)	1.0685 (17)	0.102 (3)
H8A	0.6647	0.0231	1.1541	0.153*
H8B	0.7367	0.0766	1.1435	0.153*
H8C	0.6846	0.0402	0.9549	0.153*
C9	0.6542 (13)	0.2131 (3)	1.2509 (12)	0.090 (3)
H9A	0.6845	0.2104	1.3949	0.134*
H9B	0.5876	0.2418	1.2027	0.134*
H9C	0.7414	0.2178	1.2174	0.134*
C10	0.4106 (8)	0.2446 (3)	0.4759 (11)	0.0456 (17)
C11	0.4968 (7)	0.3301 (2)	0.4216 (10)	0.0403 (15)
C12	0.3606 (8)	0.3507 (3)	0.2917 (11)	0.0508 (18)
H12A	0.2701	0.3352	0.2792	0.061*
C13	0.3614 (9)	0.3948 (2)	0.1802 (11)	0.054 (2)
H13A	0.2714	0.4088	0.0924	0.064*
C14	0.4971 (8)	0.4173 (3)	0.2018 (10)	0.0514 (19)
C15	0.6283 (9)	0.3986 (3)	0.3347 (12)	0.057 (2)
H15A	0.7182	0.4154	0.3539	0.068*
C16	0.6286 (8)	0.3538 (3)	0.4433 (11)	0.0515 (19)
H16B	0.7193	0.3402	0.5308	0.062*

	U11	U22	U33	U12	U13	U23
Br	0.0741 (5)	0.0650 (5)	0.0620 (4)	−0.0090 (6)	0.0184 (4)	0.0183 (5)
N	0.047 (3)	0.038 (3)	0.041 (3)	−0.004 (4)	0.002 (2)	0.008 (4)
O1	0.084 (4)	0.029 (3)	0.061 (3)	−0.007 (3)	0.011 (3)	−0.003 (2)
C6	0.032 (4)	0.041 (4)	0.057 (5)	0.002 (3)	0.014 (3)	−0.002 (3)
C5	0.038 (4)	0.043 (4)	0.045 (4)	0.002 (3)	0.012 (3)	0.002 (3)
O2	0.065 (4)	0.048 (3)	0.057 (4)	0.001 (3)	0.016 (3)	0.016 (3)
O3	0.081 (4)	0.064 (4)	0.040 (3)	−0.013 (3)	0.016 (3)	−0.002 (2)
C4	0.039 (4)	0.050 (5)	0.050 (4)	0.000 (3)	0.011 (3)	0.008 (3)
O4	0.041 (3)	0.051 (3)	0.059 (3)	−0.006 (3)	0.000 (3)	0.001 (2)
C3	0.043 (4)	0.047 (4)	0.051 (5)	−0.001 (3)	0.012 (4)	0.001 (3)
C2	0.040 (4)	0.046 (4)	0.045 (4)	−0.001 (3)	0.004 (3)	0.001 (3)
C1	0.027 (3)	0.038 (4)	0.041 (4)	0.002 (3)	0.010 (3)	0.003 (3)
C7	0.107 (7)	0.044 (5)	0.065 (5)	−0.008 (5)	0.016 (5)	−0.014 (4)
C8	0.089 (8)	0.086 (7)	0.109 (8)	0.022 (6)	0.013 (7)	0.042 (6)
C9	0.143 (10)	0.080 (6)	0.047 (5)	−0.047 (6)	0.037 (6)	−0.025 (4)
C10	0.034 (4)	0.046 (4)	0.050 (5)	0.005 (3)	0.008 (4)	0.002 (3)
C11	0.035 (4)	0.037 (4)	0.042 (4)	0.003 (3)	0.006 (3)	−0.001 (3)
C12	0.036 (4)	0.049 (4)	0.060 (4)	0.001 (3)	0.009 (4)	0.009 (3)
C13	0.042 (4)	0.045 (4)	0.062 (5)	0.004 (4)	0.006 (4)	0.018 (4)
C14	0.047 (5)	0.060 (5)	0.045 (4)	−0.006 (4)	0.015 (4)	−0.006 (3)
C15	0.046 (5)	0.054 (5)	0.064 (5)	−0.006 (4)	0.014 (4)	0.012 (4)
C16	0.039 (4)	0.048 (4)	0.051 (4)	−0.008 (3)	−0.003 (3)	0.003 (3)

Br—C14	1.898 (7)	C7—H7A	0.9600
N—C10	1.347 (9)	C7—H7B	0.9600
N—C11	1.413 (8)	C7—H7C	0.9600
N—H0A	0.8600	C8—H8A	0.9600
O1—C3	1.347 (8)	C8—H8B	0.9600
O1—C7	1.424 (9)	C8—H8C	0.9600
C6—C1	1.378 (9)	C9—H9A	0.9600
C6—C5	1.396 (10)	C9—H9B	0.9600
C6—H6A	0.9300	C9—H9C	0.9600
C5—C4	1.375 (10)	C11—C16	1.361 (9)
C5—O3	1.382 (8)	C11—C12	1.394 (9)
O2—C4	1.368 (8)	C12—C13	1.397 (9)
O2—C8	1.407 (11)	C12—H12A	0.9300
O3—C9	1.372 (9)	C13—C14	1.381 (10)
C4—C3	1.414 (10)	C13—H13A	0.9300
O4—C10	1.239 (8)	C14—C15	1.350 (10)
C3—C2	1.377 (9)	C15—C16	1.398 (10)
C2—C1	1.383 (9)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16B	0.9300
C1—C10	1.506 (9)
C10—N—C11	125.5 (8)	H8A—C8—H8B	109.5
C10—N—H0A	117.2	O2—C8—H8C	109.5
C11—N—H0A	117.2	H8A—C8—H8C	109.5
C3—O1—C7	116.6 (6)	H8B—C8—H8C	109.5
C1—C6—C5	119.0 (7)	O3—C9—H9A	109.5
C1—C6—H6A	120.5	O3—C9—H9B	109.5
C5—C6—H6A	120.5	H9A—C9—H9B	109.5
C4—C5—O3	116.0 (7)	O3—C9—H9C	109.5
C4—C5—C6	120.3 (7)	H9A—C9—H9C	109.5
O3—C5—C6	123.7 (7)	H9B—C9—H9C	109.5
C4—O2—C8	115.4 (6)	O4—C10—N	123.4 (7)
C9—O3—C5	118.3 (6)	O4—C10—C1	120.6 (6)
O2—C4—C5	120.7 (6)	N—C10—C1	115.9 (6)
O2—C4—C3	118.9 (6)	C16—C11—C12	120.0 (6)
C5—C4—C3	120.3 (6)	C16—C11—N	118.0 (6)
O1—C3—C2	125.9 (7)	C12—C11—N	122.0 (7)
O1—C3—C4	115.2 (6)	C11—C12—C13	119.3 (7)
C2—C3—C4	118.8 (7)	C11—C12—H12A	120.3
C3—C2—C1	120.3 (6)	C13—C12—H12A	120.3
C3—C2—H2A	119.8	C14—C13—C12	119.4 (7)
C1—C2—H2A	119.8	C14—C13—H13A	120.3
C6—C1—C2	121.2 (6)	C12—C13—H13A	120.3
C6—C1—C10	120.4 (6)	C15—C14—C13	121.1 (7)
C2—C1—C10	118.3 (6)	C15—C14—Br	119.7 (6)
O1—C7—H7A	109.5	C13—C14—Br	119.3 (6)
O1—C7—H7B	109.5	C14—C15—C16	119.7 (7)
H7A—C7—H7B	109.5	C14—C15—H15A	120.1
O1—C7—H7C	109.5	C16—C15—H15A	120.1
H7A—C7—H7C	109.5	C11—C16—C15	120.4 (7)
H7B—C7—H7C	109.5	C11—C16—H16B	119.8
O2—C8—H8A	109.5	C15—C16—H16B	119.8
O2—C8—H8B	109.5
C1—C6—C5—C4	0.2 (10)	C3—C2—C1—C6	−1.5 (10)
C1—C6—C5—O3	−179.0 (7)	C3—C2—C1—C10	−178.6 (6)
C4—C5—O3—C9	159.9 (8)	C11—N—C10—O4	−0.3 (13)
C6—C5—O3—C9	−20.9 (11)	C11—N—C10—C1	175.8 (7)
C8—O2—C4—C5	−91.1 (9)	C6—C1—C10—O4	−147.3 (7)
C8—O2—C4—C3	92.5 (9)	C2—C1—C10—O4	29.8 (9)
O3—C5—C4—O2	2.9 (10)	C6—C1—C10—N	36.4 (9)
C6—C5—C4—O2	−176.4 (6)	C2—C1—C10—N	−146.4 (7)
O3—C5—C4—C3	179.2 (7)	C10—N—C11—C16	−145.7 (8)
C6—C5—C4—C3	0.0 (10)	C10—N—C11—C12	35.4 (12)
C7—O1—C3—C2	−4.5 (11)	C16—C11—C12—C13	1.8 (10)
C7—O1—C3—C4	176.6 (7)	N—C11—C12—C13	−179.3 (7)
O2—C4—C3—O1	−5.5 (9)	C11—C12—C13—C14	−0.3 (11)
C5—C4—C3—O1	178.1 (6)	C12—C13—C14—C15	−2.7 (11)
O2—C4—C3—C2	175.5 (6)	C12—C13—C14—Br	178.1 (5)
C5—C4—C3—C2	−0.9 (11)	C13—C14—C15—C16	4.2 (12)
O1—C3—C2—C1	−177.2 (7)	Br—C14—C15—C16	−176.7 (6)
C4—C3—C2—C1	1.6 (10)	C12—C11—C16—C15	−0.4 (11)
C5—C6—C1—C2	0.6 (10)	N—C11—C16—C15	−179.3 (8)
C5—C6—C1—C10	177.6 (6)	C14—C15—C16—C11	−2.6 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O4i	0.86	2.19	2.909 (9)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O4i	0.86	2.19	2.909 (9)	140

Symmetry code: (i) .