N-(4-Amino-2-methoxy­phenyl)­acet­amide

The title compound, C₉H₁₂N₂O₂, is the product of the second step in the synthesis of N-(4-amino-3-methoxy­phenyl)­methanesulfon­amide, the side chain of an anticancer drug (viz. Amsacrine). The compound, obtained by the reduction of N-(2-methoxy-4-nitro­phenyl)­acet­amide in EtOH with Pd/C as catalyst, under a hydrogen atmosphere, crystallizes from ethyl­aceto­acetate.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.063
• wR factor = 0.225
• Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.33
         From the CIF: _reflns_number_total               1693
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         1854
         Completeness (_total/calc)             91.32%
          Alert C: < 95% complete

PLAT_353  Alert C Long  N-H Bond (0.87A)     N(11)  -   H(11A) =       1.03 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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Computing details

Data collection: KappaCCD Software (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

(I)

Crystal data

C9H12N2O2	Dx = 1.313 Mg m^−3
Mr = 180.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 12674 reflections
a = 13.9100 (2) Å	θ = 1–26.3°
b = 7.9890 (6) Å	µ = 0.09 mm^−1
c = 16.4080 (7) Å	T = 293 K
V = 1823.37 (16) Å^3	Rectangular, red
Z = 8	0.4 × 0.2 × 0.1 mm
F(000) = 768

Data collection

KappaCCD diffractometer	1532 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 26.3°, θmin = 2.5°
φ scan	h = −6→17
12674 measured reflections	k = −14→8
1693 independent reflections	l = −20→0

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.225	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ^2(Fo^2) + (0.1378P)^2 + 0.5336P] where P = (Fo^2 + 2Fc^2)/3
1693 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.34068 (9)	0.1971 (2)	0.67897 (9)	0.0428 (5)
C2	0.24254 (14)	0.2035 (2)	0.68092 (12)	0.0327 (5)
C3	0.24900 (16)	−0.0003 (3)	0.88189 (13)	0.0404 (5)
C4	0.18692 (15)	0.2786 (3)	0.62163 (12)	0.0364 (5)
H4	0.2185	0.3338	0.5688	0.044*
N5	0.26459 (12)	0.0538 (2)	0.80565 (11)	0.0410 (5)
H5	0.3286	0.0417	0.7888	0.049*
C6	0.20003 (13)	0.1276 (2)	0.74932 (10)	0.0340 (5)
C7	0.08642 (15)	0.2802 (3)	0.62891 (12)	0.0394 (5)
O8	0.16970 (13)	0.0003 (3)	0.91480 (11)	0.0644 (6)
C9	0.10118 (14)	0.1311 (3)	0.75663 (12)	0.0421 (6)
H9	0.0689	0.0821	0.8050	0.051*
C10	0.04441 (14)	0.2084 (3)	0.69760 (14)	0.0442 (6)
H10	−0.0311	0.2126	0.7031	0.053*
N11	0.03131 (14)	0.3487 (3)	0.56687 (13)	0.0612 (7)
H11A	−0.0397	0.3705	0.5819	0.073*
H11B	0.0646	0.3880	0.5165	0.073*
C12	0.38779 (16)	0.2705 (3)	0.61126 (15)	0.0499 (6)
H12A	0.4531	0.2555	0.6168	0.060*
H12B	0.3756	0.2130	0.5604	0.060*
H12C	0.3855	0.3862	0.6093	0.060*
C13	0.33733 (18)	−0.0593 (4)	0.92537 (15)	0.0545 (7)
H13A	0.3205	−0.0964	0.9792	0.065*
H13B	0.3824	0.0314	0.9291	0.065*
H13C	0.3659	−0.1502	0.8958	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0299 (8)	0.0586 (11)	0.0398 (9)	−0.0004 (6)	0.0010 (5)	0.0111 (6)
C2	0.0327 (10)	0.0338 (11)	0.0315 (10)	−0.0011 (6)	0.0005 (7)	−0.0021 (7)
C3	0.0499 (12)	0.0384 (12)	0.0328 (10)	−0.0035 (8)	0.0020 (8)	0.0011 (8)
C4	0.0373 (11)	0.0392 (12)	0.0326 (10)	0.0018 (7)	−0.0001 (7)	0.0002 (7)
N5	0.0386 (9)	0.0511 (11)	0.0333 (9)	0.0035 (7)	0.0018 (6)	0.0074 (7)
C6	0.0359 (10)	0.0357 (12)	0.0303 (10)	0.0000 (7)	0.0005 (7)	−0.0002 (7)
C7	0.0387 (11)	0.0426 (12)	0.0370 (11)	0.0059 (8)	−0.0057 (8)	−0.0032 (7)
O8	0.0557 (11)	0.0954 (16)	0.0421 (10)	−0.0068 (9)	0.0096 (7)	0.0141 (9)
C9	0.0392 (11)	0.0483 (14)	0.0389 (11)	−0.0030 (8)	0.0073 (8)	0.0004 (8)
C10	0.0327 (10)	0.0539 (14)	0.0461 (12)	0.0018 (8)	0.0007 (8)	−0.0010 (9)
N11	0.0438 (11)	0.0869 (17)	0.0528 (12)	0.0180 (10)	−0.0068 (9)	0.0140 (11)
C12	0.0403 (11)	0.0635 (15)	0.0459 (13)	−0.0030 (9)	0.0091 (9)	0.0104 (10)
C13	0.0636 (16)	0.0626 (17)	0.0374 (12)	0.0050 (11)	−0.0042 (9)	0.0086 (10)

Geometric parameters (Å, º)

O1—C2	1.366 (2)	C7—C10	1.393 (3)
O1—C12	1.417 (3)	C9—C10	1.394 (3)
C2—C4	1.380 (3)	C9—H9	0.9925
C2—C6	1.406 (3)	C10—H10	1.0552
C3—O8	1.228 (3)	N11—H11A	1.0334
C3—N5	1.341 (3)	N11—H11B	0.9980
C3—C13	1.497 (3)	C12—H12A	0.9211
C4—C7	1.403 (3)	C12—H12B	0.9676
C4—H4	1.0666	C12—H12C	0.9253
N5—C6	1.417 (2)	C13—H13A	0.9600
N5—H5	0.9377	C13—H13B	0.9601
C6—C9	1.381 (3)	C13—H13C	0.9600
C7—N11	1.387 (3)
C2—O1—C12	117.73 (16)	C6—C9—H9	120.8
O1—C2—C4	124.02 (18)	C10—C9—H9	118.3
O1—C2—C6	115.01 (17)	C7—C10—C9	120.47 (18)
C4—C2—C6	120.96 (18)	C7—C10—H10	118.3
O8—C3—N5	123.7 (2)	C9—C10—H10	121.2
O8—C3—C13	121.9 (2)	C7—N11—H11A	114.8
N5—C3—C13	114.41 (19)	C7—N11—H11B	118.4
C2—C4—C7	120.16 (18)	H11A—N11—H11B	126.0
C2—C4—H4	121.4	O1—C12—H12A	109.0
C7—C4—H4	118.4	O1—C12—H12B	113.5
C3—N5—C6	129.78 (17)	H12A—C12—H12B	101.3
C3—N5—H5	113.3	O1—C12—H12C	115.1
C6—N5—H5	116.9	H12A—C12—H12C	99.6
C9—C6—C2	118.65 (17)	H12B—C12—H12C	116.0
C9—C6—N5	125.66 (17)	C3—C13—H13A	109.6
C2—C6—N5	115.69 (16)	C3—C13—H13B	109.1
N11—C7—C10	121.63 (19)	H13A—C13—H13B	109.5
N11—C7—C4	119.47 (19)	C3—C13—H13C	109.7
C10—C7—C4	118.88 (18)	H13A—C13—H13C	109.5
C6—C9—C10	120.85 (18)	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O1	0.94	2.19	2.598 (2)	105
N11—H11A···O8^i	1.03	2.09	3.062 (3)	157
N11—H11B···O8^ii	1.00	2.39	3.374 (3)	168

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