3,4,5-Trimeth-oxy-N-(2-methoxy-phen-yl)benzamide.

In the title mol-ecule, C(17)H(19)NO(5), the amide plane is oriented at an angle of 41.5 (3)° with respect to the 2-methoxy-benzene ring. The three meth-oxy 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 meth-oxy group at the 4-position of the 3,4,5-trimethoxy-benzene ring is nearly perpendicularly oriented [C-O-C-C torsion angle of 103.9 (3)°]. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along [001].

Related literature

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

Experimental

Crystal data

C17H19NO5

M = 317.33

Orthorhombic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: SHELXTL.

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

C17H19NO5	F(000) = 672
Mr = 317.33	Dx = 1.305 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 887 reflections
a = 7.409 (2) Å	θ = 2.9–27.6°
b = 22.522 (6) Å	µ = 0.10 mm−1
c = 9.681 (3) Å	T = 120 K
V = 1615.4 (7) Å3	Prism, colourless
Z = 4	0.50 × 0.44 × 0.20 mm

Bruker SMART APEX diffractometer	2050 independent reflections
Radiation source: sealed tube	1902 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.953, Tmax = 0.981	k = −29→25
13253 measured reflections	l = −12→12

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

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
O1	0.1314 (3)	0.22502 (9)	1.0268 (2)	0.0232 (5)
O2	−0.0063 (3)	0.16331 (10)	0.5858 (2)	0.0246 (5)
O3	0.7319 (3)	0.33720 (9)	0.7087 (2)	0.0258 (5)
O4	0.6652 (3)	0.43489 (9)	0.8620 (3)	0.0246 (5)
O5	0.4036 (3)	0.43643 (9)	1.0503 (3)	0.0263 (5)
N1	0.1909 (3)	0.19743 (11)	0.8055 (3)	0.0199 (5)
H1	0.232 (7)	0.2095 (18)	0.723 (3)	0.053 (13)*
C1	0.2067 (3)	0.23480 (13)	0.9166 (3)	0.0186 (6)
C2	0.0968 (3)	0.14253 (13)	0.8110 (3)	0.0189 (6)
C3	0.1076 (4)	0.10537 (14)	0.9251 (4)	0.0242 (6)
H3A	0.1804	0.1163	1.0018	0.029*
C4	0.0117 (4)	0.05177 (14)	0.9278 (4)	0.0285 (7)
H4A	0.0179	0.0268	1.0068	0.034*
C5	−0.0923 (4)	0.03511 (14)	0.8150 (4)	0.0294 (7)
H5A	−0.1575	−0.0012	0.8169	0.035*
C6	−0.1012 (4)	0.07152 (14)	0.6989 (4)	0.0270 (7)
H6A	−0.1718	0.0598	0.6217	0.032*
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	−0.0681	0.1089	0.4312	0.057*
H8B	−0.0996	0.1776	0.3961	0.057*
H8C	−0.2385	0.1432	0.4942	0.057*
C9	0.3260 (4)	0.28794 (12)	0.8974 (3)	0.0167 (5)
C10	0.4689 (4)	0.28683 (13)	0.8036 (3)	0.0183 (5)
H10A	0.4859	0.2532	0.7457	0.022*
C11	0.5872 (4)	0.33511 (13)	0.7945 (3)	0.0181 (5)
C12	0.5583 (4)	0.38548 (13)	0.8771 (3)	0.0204 (6)
C13	0.4143 (4)	0.38603 (12)	0.9724 (3)	0.0194 (6)
C14	0.2986 (4)	0.33723 (12)	0.9835 (3)	0.0190 (6)
H14A	0.2026	0.3374	1.0486	0.023*
C15	0.7858 (5)	0.28235 (14)	0.6464 (4)	0.0328 (8)
H15A	0.7979	0.2518	0.7179	0.049*
H15B	0.9019	0.2877	0.5995	0.049*
H15C	0.6945	0.2700	0.5790	0.049*
C16	0.8392 (5)	0.42964 (16)	0.9272 (5)	0.0367 (9)
H16A	0.8234	0.4255	1.0273	0.055*
H16B	0.9109	0.4652	0.9077	0.055*
H16C	0.9018	0.3946	0.8911	0.055*
C17	0.2685 (5)	0.43817 (14)	1.1558 (4)	0.0323 (7)
H17A	0.1487	0.4352	1.1135	0.048*
H17B	0.2779	0.4757	1.2067	0.048*
H17C	0.2865	0.4049	1.2195	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0229 (10)	0.0307 (11)	0.0159 (10)	−0.0039 (8)	0.0057 (9)	−0.0036 (9)
O2	0.0247 (11)	0.0311 (11)	0.0179 (10)	−0.0079 (9)	−0.0033 (8)	−0.0018 (9)
O3	0.0239 (10)	0.0295 (10)	0.0242 (12)	−0.0046 (9)	0.0100 (10)	−0.0015 (9)
O4	0.0241 (10)	0.0229 (11)	0.0268 (11)	−0.0044 (8)	0.0023 (9)	0.0033 (9)
O5	0.0285 (11)	0.0234 (10)	0.0270 (13)	−0.0027 (8)	0.0081 (10)	−0.0053 (9)
N1	0.0205 (11)	0.0271 (12)	0.0121 (11)	−0.0043 (9)	0.0007 (10)	−0.0019 (10)
C1	0.0142 (12)	0.0266 (14)	0.0150 (13)	0.0016 (10)	−0.0024 (10)	−0.0014 (11)
C2	0.0150 (12)	0.0240 (14)	0.0176 (14)	0.0001 (10)	0.0058 (11)	−0.0033 (12)
C3	0.0207 (14)	0.0289 (15)	0.0231 (16)	0.0044 (11)	0.0028 (12)	−0.0002 (12)
C4	0.0266 (15)	0.0269 (15)	0.0320 (18)	0.0057 (12)	0.0090 (14)	0.0062 (14)
C5	0.0242 (14)	0.0203 (14)	0.044 (2)	−0.0035 (11)	0.0069 (15)	−0.0030 (14)
C6	0.0223 (14)	0.0281 (15)	0.0307 (18)	−0.0025 (12)	0.0014 (13)	−0.0079 (13)
C7	0.0180 (13)	0.0242 (14)	0.0211 (15)	0.0006 (11)	0.0042 (11)	−0.0033 (12)
C8	0.0381 (19)	0.049 (2)	0.0276 (18)	−0.0158 (16)	−0.0144 (16)	0.0038 (17)
C9	0.0160 (12)	0.0243 (13)	0.0098 (12)	−0.0004 (10)	−0.0027 (10)	−0.0004 (10)
C10	0.0207 (12)	0.0245 (13)	0.0098 (12)	0.0018 (10)	−0.0005 (11)	−0.0018 (11)
C11	0.0163 (11)	0.0272 (14)	0.0107 (13)	0.0006 (10)	0.0026 (10)	0.0014 (11)
C12	0.0223 (13)	0.0218 (14)	0.0171 (14)	0.0000 (11)	−0.0036 (11)	0.0038 (11)
C13	0.0197 (13)	0.0228 (14)	0.0156 (14)	0.0015 (10)	−0.0031 (11)	0.0001 (12)
C14	0.0178 (12)	0.0275 (14)	0.0118 (12)	0.0025 (10)	−0.0008 (11)	−0.0007 (11)
C15	0.0301 (17)	0.0315 (15)	0.0368 (19)	−0.0044 (12)	0.0173 (16)	−0.0034 (16)
C16	0.0308 (17)	0.0338 (19)	0.045 (2)	−0.0093 (14)	−0.0069 (17)	0.0000 (16)
C17	0.0352 (17)	0.0316 (15)	0.0300 (18)	−0.0030 (14)	0.0107 (16)	−0.0127 (15)

O1—C1	1.224 (4)	C6—H6A	0.9500
O2—C7	1.366 (4)	C8—H8A	0.9800
O2—C8	1.434 (4)	C8—H8B	0.9800
O3—C11	1.357 (3)	C8—H8C	0.9800
O3—C15	1.432 (4)	C9—C10	1.395 (4)
O4—C12	1.374 (4)	C9—C14	1.403 (4)
O4—C16	1.441 (4)	C10—C11	1.400 (4)
O5—C13	1.365 (4)	C10—H10A	0.9500
O5—C17	1.431 (4)	C11—C12	1.404 (4)
N1—C1	1.371 (4)	C12—C13	1.410 (4)
N1—C2	1.420 (4)	C13—C14	1.398 (4)
N1—H1	0.895 (10)	C14—H14A	0.9500
C1—C9	1.500 (4)	C15—H15A	0.9800
C2—C3	1.388 (4)	C15—H15B	0.9800
C2—C7	1.412 (4)	C15—H15C	0.9800
C3—C4	1.401 (5)	C16—H16A	0.9800
C3—H3A	0.9500	C16—H16B	0.9800
C4—C5	1.389 (5)	C16—H16C	0.9800
C4—H4A	0.9500	C17—H17A	0.9800
C5—C6	1.392 (5)	C17—H17B	0.9800
C5—H5A	0.9500	C17—H17C	0.9800
C6—C7	1.396 (4)
C7—O2—C8	117.3 (2)	C10—C9—C1	120.9 (2)
C11—O3—C15	116.7 (2)	C14—C9—C1	118.2 (2)
C12—O4—C16	113.8 (3)	C9—C10—C11	120.1 (3)
C13—O5—C17	117.3 (2)	C9—C10—H10A	119.9
C1—N1—C2	123.1 (2)	C11—C10—H10A	119.9
C1—N1—H1	119 (3)	O3—C11—C10	124.1 (3)
C2—N1—H1	118 (3)	O3—C11—C12	116.2 (2)
O1—C1—N1	122.3 (3)	C10—C11—C12	119.8 (3)
O1—C1—C9	121.4 (3)	O4—C12—C11	120.4 (3)
N1—C1—C9	116.3 (2)	O4—C12—C13	119.9 (3)
C3—C2—C7	119.7 (3)	C11—C12—C13	119.7 (3)
C3—C2—N1	121.8 (3)	O5—C13—C14	125.1 (3)
C7—C2—N1	118.6 (3)	O5—C13—C12	114.4 (2)
C2—C3—C4	120.3 (3)	C14—C13—C12	120.5 (3)
C2—C3—H3A	119.8	C13—C14—C9	119.1 (3)
C4—C3—H3A	119.8	C13—C14—H14A	120.4
C5—C4—C3	120.0 (3)	C9—C14—H14A	120.4
C5—C4—H4A	120.0	O3—C15—H15A	109.5
C3—C4—H4A	120.0	O3—C15—H15B	109.5
C4—C5—C6	120.1 (3)	H15A—C15—H15B	109.5
C4—C5—H5A	119.9	O3—C15—H15C	109.5
C6—C5—H5A	119.9	H15A—C15—H15C	109.5
C5—C6—C7	120.3 (3)	H15B—C15—H15C	109.5
C5—C6—H6A	119.8	O4—C16—H16A	109.5
C7—C6—H6A	119.8	O4—C16—H16B	109.5
O2—C7—C6	124.3 (3)	H16A—C16—H16B	109.5
O2—C7—C2	116.1 (2)	O4—C16—H16C	109.5
C6—C7—C2	119.6 (3)	H16A—C16—H16C	109.5
O2—C8—H8A	109.5	H16B—C16—H16C	109.5
O2—C8—H8B	109.5	O5—C17—H17A	109.5
H8A—C8—H8B	109.5	O5—C17—H17B	109.5
O2—C8—H8C	109.5	H17A—C17—H17B	109.5
H8A—C8—H8C	109.5	O5—C17—H17C	109.5
H8B—C8—H8C	109.5	H17A—C17—H17C	109.5
C10—C9—C14	120.7 (3)	H17B—C17—H17C	109.5
C2—N1—C1—O1	−4.4 (4)	C1—C9—C10—C11	−175.1 (3)
C2—N1—C1—C9	174.0 (2)	C15—O3—C11—C10	−13.4 (4)
C1—N1—C2—C3	−39.8 (4)	C15—O3—C11—C12	167.1 (3)
C1—N1—C2—C7	141.6 (3)	C9—C10—C11—O3	178.4 (3)
C7—C2—C3—C4	−2.0 (4)	C9—C10—C11—C12	−2.0 (4)
N1—C2—C3—C4	179.4 (3)	C16—O4—C12—C11	−78.5 (4)
C2—C3—C4—C5	1.1 (5)	C16—O4—C12—C13	103.9 (3)
C3—C4—C5—C6	0.1 (5)	O3—C11—C12—O4	4.5 (4)
C4—C5—C6—C7	−0.5 (5)	C10—C11—C12—O4	−175.1 (3)
C8—O2—C7—C6	0.7 (4)	O3—C11—C12—C13	−177.9 (3)
C8—O2—C7—C2	−179.6 (3)	C10—C11—C12—C13	2.5 (4)
C5—C6—C7—O2	179.2 (3)	C17—O5—C13—C14	3.1 (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—O2	0.6 (4)	C11—C12—C13—O5	177.7 (3)
C3—C2—C7—C6	1.7 (4)	O4—C12—C13—C14	176.6 (3)
N1—C2—C7—C6	−179.7 (3)	C11—C12—C13—C14	−1.1 (4)
O1—C1—C9—C10	151.4 (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—C13	1.3 (4)
N1—C1—C9—C14	157.6 (2)	C1—C9—C14—C13	176.7 (2)
C14—C9—C10—C11	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90 (1)	2.18 (1)	3.066 (4)	169 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.895 (10)	2.182 (14)	3.066 (4)	169 (4)

Symmetry code: (i) .