3,5-Dimethoxy­acetanilide

Lai, Q.-L.; Zhao, Q.-J.; Liu, Z.; Shen, J.-S.

doi:10.1107/S1600536807020600

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3,5-Dimethoxyacetanilide

Q.-L. Lai, Q.-J. Zhao, Z. Liu and J.-S. Shen

The title compound, C₁₀H₁₃NO₃, crystallizes with two molecules in the asymmetric unit. Molecules related by an a-axis translation are stacked over each other, bound by π–π interactions with a perpendicular distance of 3.455 Å. Molecules in adjacent stacks are linked to each other through N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020600/om2120sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020600/om2120Isup2.hkl Contains datablock I

CCDC reference: 651366

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.108
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), is an important intermediate used to synthesize a variety of pharmaceuticals, such as epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (Traxler et al., 1999). In our recent research for the synthesis of potential PDE5 inhitiors, 3,5-dimethoxyanilide (I) was synthesized as one of the structural units. We report here the crystal structure of the title compound, which crystallizes with two molecules in the asymmetric unit.

A view of the molecular structure of (I) is depicted in Fig. 1. In the two distinct molecules, the N-acetyl group is oriented at angles of 3.10 (2)° and 20.00 (3)° to the aromatic plane. All bond lengths and angles are normal (Allen et al., 1987). Molecules related by an a-axis translation are stacked over each other and the perpendicular distance between the stacking planes is 3.455Å (Fig. 2). It is, therefore, inferred that the stacked molecules are bound to each other by π-π interactions (Hunter & Sanders, 1990). The stacked columns are linked together via an intermolecular hydrogen bond in which the amide H act as a donor to O atom (Fig. 2 and Table 1).

Related literature top

For related literature, see: Allen et al. (1987); Hall et al. (1992); Hunter & Sanders (1990); Traxler et al. (1999).

Experimental top

The title compound was prepared by acetylation of 3,5-dimethoxyaniline according to the method described by Hall et al., (1992). Single crystals suitable for X-ray analysis (m.p. 426 K) were obtained by slow evaporation of a dichloromethane solution at 298 K.

Structure description top

For related literature, see: Allen et al. (1987); Hall et al. (1992); Hunter & Sanders (1990); Traxler et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The crystal packing of (I), viewed along the 〈i〉a〈/i〉 axis. Hydrogen bonds are shown as dashed lines.

3,5-Dimethoxyacetanilide top

Crystal data top

C₁₀H₁₃NO₃	D_x = 1.296 Mg m⁻³
M_r = 195.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4958 reflections
a = 7.1956 (6) Å	θ = 2.5–24.7°
b = 16.8320 (14) Å	µ = 0.10 mm⁻¹
c = 33.054 (3) Å	T = 293 K
V = 4003.4 (6) Å³	Block, colourless
Z = 16	0.30 × 0.20 × 0.20 mm
F(000) = 1664

Data collection top

Bruker SMART APEXII diffractometer	3548 independent reflections
Radiation source: fine-focus sealed tube	2808 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.972, T_max = 0.981	k = −19→20
19389 measured reflections	l = −30→39

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.047P)² + 1.2714P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3548 reflections	Δρ_max = 0.25 e Å⁻³
260 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (4)

Crystal data top

C₁₀H₁₃NO₃	V = 4003.4 (6) Å³
M_r = 195.21	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 7.1956 (6) Å	µ = 0.10 mm⁻¹
b = 16.8320 (14) Å	T = 293 K
c = 33.054 (3) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII diffractometer	3548 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2808 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.033
19389 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
3548 reflections	Δρ_min = −0.14 e Å⁻³
260 parameters

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
C1	0.9040 (2)	0.66216 (10)	0.91166 (5)	0.0360 (4)
C2	0.7495 (2)	0.70799 (10)	0.92004 (5)	0.0416 (4)
H2	0.7399	0.7590	0.9095	0.050*
C3	0.6087 (2)	0.67783 (11)	0.94428 (5)	0.0430 (4)
C4	0.6212 (3)	0.60184 (11)	0.96012 (5)	0.0464 (5)
H4	0.5277	0.5817	0.9766	0.056*
C5	0.7761 (3)	0.55664 (10)	0.95083 (5)	0.0428 (4)
C6	0.9191 (2)	0.58522 (10)	0.92700 (5)	0.0404 (4)
H6	1.0226	0.5540	0.9214	0.048*
C7	1.2042 (2)	0.66862 (10)	0.87336 (5)	0.0410 (4)
C8	1.3073 (3)	0.72307 (12)	0.84542 (7)	0.0596 (6)
H8A	1.4291	0.7331	0.8561	0.089*
H8B	1.2409	0.7723	0.8430	0.089*
H8C	1.3181	0.6987	0.8193	0.089*
C9	0.3195 (3)	0.70352 (14)	0.97704 (7)	0.0659 (6)
H9A	0.2630	0.6562	0.9665	0.099*
H9B	0.2275	0.7446	0.9792	0.099*
H9C	0.3705	0.6926	1.0033	0.099*
C10	0.9237 (3)	0.42958 (11)	0.95603 (7)	0.0647 (6)
H10A	0.9281	0.4240	0.9271	0.097*
H10B	0.9047	0.3784	0.9682	0.097*
H10C	1.0388	0.4516	0.9655	0.097*
C11	0.7292 (2)	0.50583 (10)	0.83936 (5)	0.0371 (4)
C12	0.8709 (2)	0.45172 (10)	0.83355 (5)	0.0412 (4)
H12	0.8650	0.4016	0.8454	0.049*
C13	1.0227 (2)	0.47288 (10)	0.80982 (5)	0.0420 (4)
C14	1.0337 (3)	0.54668 (11)	0.79191 (5)	0.0460 (4)
H14	1.1359	0.5604	0.7761	0.055*
C15	0.8897 (3)	0.60002 (10)	0.79786 (5)	0.0454 (5)
C16	0.7373 (3)	0.58076 (10)	0.82121 (5)	0.0426 (4)
H16	0.6414	0.6171	0.8248	0.051*
C17	0.5121 (2)	0.41904 (10)	0.87722 (5)	0.0424 (4)
C18	0.3505 (3)	0.42184 (12)	0.90562 (7)	0.0607 (6)
H18A	0.2966	0.3698	0.9078	0.091*
H18B	0.2591	0.4583	0.8955	0.091*
H18C	0.3919	0.4392	0.9318	0.091*
C19	1.3080 (3)	0.43027 (14)	0.78001 (6)	0.0651 (6)
H19A	1.2630	0.4393	0.7530	0.098*
H19B	1.3903	0.3854	0.7800	0.098*
H19C	1.3736	0.4765	0.7893	0.098*
C20	0.7776 (3)	0.73162 (12)	0.78511 (7)	0.0663 (6)
H20A	0.6589	0.7135	0.7756	0.099*
H20B	0.8127	0.7787	0.7706	0.099*
H20C	0.7697	0.7434	0.8135	0.099*
N1	1.03993 (19)	0.69747 (8)	0.88680 (4)	0.0405 (4)
H1	1.0144	0.7449	0.8789	0.049*
N2	0.5737 (2)	0.49023 (8)	0.86409 (4)	0.0418 (4)
H2A	0.5105	0.5310	0.8717	0.050*
O1	0.46382 (18)	0.72883 (8)	0.95061 (4)	0.0596 (4)
O2	0.77427 (19)	0.48116 (8)	0.96687 (4)	0.0603 (4)
O3	1.26690 (17)	0.60353 (7)	0.88250 (4)	0.0516 (4)
O4	1.15542 (19)	0.41493 (8)	0.80618 (4)	0.0606 (4)
O5	0.9123 (2)	0.67166 (8)	0.77872 (5)	0.0684 (4)
O6	0.58211 (19)	0.35588 (7)	0.86658 (4)	0.0593 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0339 (9)	0.0350 (9)	0.0390 (9)	−0.0056 (7)	−0.0013 (7)	0.0005 (7)
C2	0.0427 (10)	0.0338 (9)	0.0483 (10)	−0.0018 (8)	0.0016 (8)	0.0004 (8)
C3	0.0389 (10)	0.0420 (10)	0.0481 (10)	−0.0026 (8)	0.0049 (8)	−0.0096 (8)
C4	0.0449 (11)	0.0473 (11)	0.0472 (11)	−0.0106 (9)	0.0100 (9)	−0.0012 (9)
C5	0.0464 (10)	0.0379 (10)	0.0442 (10)	−0.0077 (8)	0.0019 (9)	0.0046 (8)
C6	0.0393 (9)	0.0346 (9)	0.0472 (10)	−0.0029 (8)	0.0015 (8)	0.0032 (8)
C7	0.0388 (9)	0.0355 (10)	0.0488 (10)	−0.0020 (8)	0.0023 (8)	0.0045 (8)
C8	0.0496 (12)	0.0519 (12)	0.0772 (14)	0.0034 (10)	0.0167 (11)	0.0182 (10)
C9	0.0507 (12)	0.0783 (16)	0.0687 (14)	−0.0001 (11)	0.0212 (11)	−0.0086 (12)
C10	0.0717 (14)	0.0412 (11)	0.0811 (15)	0.0054 (10)	0.0221 (12)	0.0182 (10)
C11	0.0434 (10)	0.0345 (9)	0.0334 (9)	−0.0049 (8)	0.0004 (8)	−0.0004 (7)
C12	0.0476 (10)	0.0356 (9)	0.0402 (10)	−0.0011 (8)	0.0036 (8)	0.0060 (8)
C13	0.0433 (10)	0.0430 (10)	0.0395 (10)	0.0013 (8)	0.0008 (8)	0.0013 (8)
C14	0.0432 (10)	0.0491 (11)	0.0458 (10)	−0.0093 (9)	0.0047 (8)	0.0052 (9)
C15	0.0540 (11)	0.0349 (10)	0.0473 (10)	−0.0089 (9)	−0.0012 (9)	0.0072 (8)
C16	0.0475 (10)	0.0328 (9)	0.0474 (10)	−0.0007 (8)	0.0019 (9)	0.0020 (8)
C17	0.0418 (10)	0.0371 (10)	0.0484 (11)	−0.0006 (8)	0.0018 (9)	0.0091 (8)
C18	0.0609 (13)	0.0515 (12)	0.0698 (14)	0.0009 (10)	0.0218 (11)	0.0146 (10)
C19	0.0476 (12)	0.0824 (16)	0.0652 (14)	0.0079 (11)	0.0153 (11)	0.0046 (12)
C20	0.0742 (15)	0.0407 (11)	0.0838 (16)	−0.0050 (11)	−0.0032 (13)	0.0169 (11)
N1	0.0377 (8)	0.0306 (7)	0.0533 (9)	0.0007 (6)	0.0051 (7)	0.0097 (6)
N2	0.0471 (9)	0.0312 (8)	0.0473 (9)	0.0012 (7)	0.0114 (7)	0.0023 (6)
O1	0.0494 (8)	0.0505 (8)	0.0788 (10)	0.0038 (6)	0.0238 (7)	−0.0031 (7)
O2	0.0619 (9)	0.0446 (8)	0.0742 (9)	−0.0014 (7)	0.0207 (8)	0.0197 (7)
O3	0.0492 (8)	0.0363 (7)	0.0694 (9)	0.0076 (6)	0.0107 (7)	0.0104 (6)
O4	0.0530 (8)	0.0597 (9)	0.0691 (9)	0.0127 (7)	0.0207 (7)	0.0153 (7)
O5	0.0704 (10)	0.0442 (8)	0.0907 (11)	−0.0032 (7)	0.0199 (8)	0.0249 (7)
O6	0.0538 (8)	0.0321 (7)	0.0920 (11)	0.0036 (6)	0.0194 (8)	0.0095 (7)

Geometric parameters (Å, º) top

C1—C2	1.381 (2)	C11—C16	1.398 (2)
C1—C6	1.395 (2)	C11—N2	1.410 (2)
C1—N1	1.409 (2)	C12—C13	1.391 (2)
C2—C3	1.388 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—O4	1.371 (2)
C3—O1	1.366 (2)	C13—C14	1.378 (2)
C3—C4	1.385 (3)	C14—C15	1.385 (3)
C4—C5	1.384 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—O5	1.371 (2)
C5—O2	1.377 (2)	C15—C16	1.379 (2)
C5—C6	1.382 (2)	C16—H16	0.9300
C6—H6	0.9300	C17—O6	1.228 (2)
C7—O3	1.223 (2)	C17—N2	1.349 (2)
C7—N1	1.353 (2)	C17—C18	1.495 (3)
C7—C8	1.498 (2)	C18—H18A	0.9600
C8—H8A	0.9600	C18—H18B	0.9600
C8—H8B	0.9600	C18—H18C	0.9600
C8—H8C	0.9600	C19—O4	1.421 (2)
C9—O1	1.423 (2)	C19—H19A	0.9600
C9—H9A	0.9600	C19—H19B	0.9600
C9—H9B	0.9600	C19—H19C	0.9600
C9—H9C	0.9600	C20—O5	1.415 (3)
C10—O2	1.428 (2)	C20—H20A	0.9600
C10—H10A	0.9600	C20—H20B	0.9600
C10—H10B	0.9600	C20—H20C	0.9600
C10—H10C	0.9600	N1—H1	0.8600
C11—C12	1.381 (2)	N2—H2A	0.8600

C2—C1—C6	120.54 (16)	C13—C12—H12	120.3
C2—C1—N1	116.11 (14)	O4—C13—C14	124.29 (16)
C6—C1—N1	123.34 (15)	O4—C13—C12	114.49 (15)
C1—C2—C3	119.96 (16)	C14—C13—C12	121.23 (17)
C1—C2—H2	120.0	C13—C14—C15	118.67 (17)
C3—C2—H2	120.0	C13—C14—H14	120.7
O1—C3—C4	124.89 (16)	C15—C14—H14	120.7
O1—C3—C2	114.56 (16)	O5—C15—C16	124.01 (17)
C4—C3—C2	120.56 (17)	O5—C15—C14	114.53 (16)
C5—C4—C3	118.43 (16)	C16—C15—C14	121.46 (16)
C5—C4—H4	120.8	C15—C16—C11	119.05 (17)
C3—C4—H4	120.8	C15—C16—H16	120.5
O2—C5—C6	123.21 (16)	C11—C16—H16	120.5
O2—C5—C4	114.46 (16)	O6—C17—N2	122.81 (16)
C6—C5—C4	122.32 (16)	O6—C17—C18	121.76 (16)
C5—C6—C1	118.18 (16)	N2—C17—C18	115.43 (16)
C5—C6—H6	120.9	C17—C18—H18A	109.5
C1—C6—H6	120.9	C17—C18—H18B	109.5
O3—C7—N1	124.26 (16)	H18A—C18—H18B	109.5
O3—C7—C8	121.16 (16)	C17—C18—H18C	109.5
N1—C7—C8	114.57 (15)	H18A—C18—H18C	109.5
C7—C8—H8A	109.5	H18B—C18—H18C	109.5
C7—C8—H8B	109.5	O4—C19—H19A	109.5
H8A—C8—H8B	109.5	O4—C19—H19B	109.5
C7—C8—H8C	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	O4—C19—H19C	109.5
H8B—C8—H8C	109.5	H19A—C19—H19C	109.5
O1—C9—H9A	109.5	H19B—C19—H19C	109.5
O1—C9—H9B	109.5	O5—C20—H20A	109.5
H9A—C9—H9B	109.5	O5—C20—H20B	109.5
O1—C9—H9C	109.5	H20A—C20—H20B	109.5
H9A—C9—H9C	109.5	O5—C20—H20C	109.5
H9B—C9—H9C	109.5	H20A—C20—H20C	109.5
O2—C10—H10A	109.5	H20B—C20—H20C	109.5
O2—C10—H10B	109.5	C7—N1—C1	130.28 (14)
H10A—C10—H10B	109.5	C7—N1—H1	114.9
O2—C10—H10C	109.5	C1—N1—H1	114.9
H10A—C10—H10C	109.5	C17—N2—C11	127.76 (15)
H10B—C10—H10C	109.5	C17—N2—H2A	116.1
C12—C11—C16	120.29 (16)	C11—N2—H2A	116.1
C12—C11—N2	122.95 (15)	C3—O1—C9	117.57 (16)
C16—C11—N2	116.74 (15)	C5—O2—C10	117.22 (14)
C11—C12—C13	119.30 (16)	C13—O4—C19	117.55 (15)
C11—C12—H12	120.3	C15—O5—C20	118.46 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86	2.03	2.8857 (18)	171
N2—H2A···O3ⁱⁱ	0.86	2.17	2.9799 (19)	158

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₃
M_r	195.21
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	7.1956 (6), 16.8320 (14), 33.054 (3)
V (Å³)	4003.4 (6)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	19389, 3548, 2808
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 1.03
No. of reflections	3548
No. of parameters	260
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.14

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86	2.03	2.8857 (18)	170.6
N2—H2A···O3ⁱⁱ	0.86	2.17	2.9799 (19)	157.7

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1, y, z.

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