N-(4-Bromo­phen­yl)-3,4,5-trimeth­oxy­benzamide

Gu, W.; Qiao, C.

doi:10.1107/S1600536812018946

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1658

doi:10.1107/S1600536812018946

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N-(4-Bromophenyl)-3,4,5-trimethoxybenzamide

Wen Gu ^a ^* and Chao Qiao ^a

^aCollege of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, People's Republic of China
^*Correspondence e-mail: njguwen@163.com

(Received 25 April 2012; accepted 27 April 2012; online 5 May 2012)

In the title compound, C₁₆H₁₆BrNO₄, the dihedral angle between the two aromatic rings is 67.51 (25)°. In the crystal, molecules 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_r = 366.21
Monoclinic, C c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.094
S = 1.00
1616 reflections
199 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 91 Friedel pairs
Flack parameter: 0.010 (17)

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018946/kp2410sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812018946/kp2410Isup3.cml

checkCIF report

Comment top

As a part of our ongoing research on the synthesis and biological activities of 3,4,5-trimethoxy-benzamide derivatives, the title compound (I) was synthesised and its crystal structure was determined (Fig. 1). In the crystal packing N-H···O hydrogen bond generates a chain along [101] (Table 1).

Related literature top

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 top

To a solution of 3,4,5-Trimethoxybenzoyl chloride (1.15 g, 5 mmol) in benzene (20 mL) was added 4-bromoaniline (0.95 g, 5.5 mmol) and triethylamine (0.56 g, 5.5 mmol). The mixture was stirred at room temperature for 12 h. After cooling, the reaction mixture was filtered to remove precipitate, and the filtrate was evaporated in vacuo to afford a white solid, which was recrystalised in EtOH to give the title compound (I) as a colourless prisms (1.5 g, 82%). Single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol solution at room temperature over 7 d.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) with 30% probability displacement ellipsoids for non-H atoms.

N-(4-Bromophenyl)-3,4,5-trimethoxybenzamide top

Crystal data top

C₁₆H₁₆BrNO₄	F(000) = 744
M_r = 366.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.043P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1616 reflections	Δρ_max = 0.37 e Å⁻³
199 parameters	Δρ_min = −0.26 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 91 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (17)

Crystal data top

C₁₆H₁₆BrNO₄	V = 1649.9 (6) Å³
M_r = 366.21	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 9.5860 (19) Å	µ = 2.51 mm⁻¹
b = 26.010 (5) Å	T = 293 K
c = 7.1390 (14) Å	0.20 × 0.10 × 0.10 mm
β = 112.04 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1206 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.064
T_min = 0.634, T_max = 0.788	3 standard reflections every 200 reflections
3194 measured reflections	intensity decay: 1%
1616 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.37 e Å⁻³
S = 1.00	Δρ_min = −0.26 e Å⁻³
1616 reflections	Absolute structure: Flack (1983), 91 Friedel pairs
199 parameters	Absolute structure parameter: 0.010 (17)
2 restraints

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆BrNO₄
M_r	366.21
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	9.5860 (19), 26.010 (5), 7.1390 (14)
β (°)	112.04 (3)
V (Å³)	1649.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.51
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.634, 0.788
No. of measured, independent and observed [I > 2σ(I)] reflections	3194, 1616, 1206
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.094, 1.00
No. of reflections	1616
No. of parameters	199
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26
Absolute structure	Flack (1983), 91 Friedel pairs
Absolute structure parameter	0.010 (17)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O4ⁱ	0.86	2.19	2.909 (9)	140.3

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The work was supported by a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD). The authors thank Professor H. Q. Wang of the Center for Testing and Analysis, Nanjing University, for the collection of the X-ray diffraction data.

References

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