N-(4-Meth­oxy-2-nitro­phen­yl)acetamide

In the title compound, C₉H₁₀N₂O₄, the three substituents vary in the degree of lack of planarity with the central phenyl ring. The meth­oxy group is nearest to being coplanar, with a C—C—O—C torsion angle of 6.1 (5)°. The nitro group is less coplanar, with a 12.8 (5)° twist about the C—N bond and the acetamido group is considerably less coplanar with the central ring, having a 25.4 (5)° twist about the C—N bond to the ring. The NH group forms an intra­molecular N—H...O hydrogen bond to a nitro-group O atom.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.071
• wR factor = 0.203
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.122
PLAT020_ALERT_3_C The Value of Rint is Greater Than 0.12 .........      0.122 Report
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B      ..O3       .       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C      ..O4       .       2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.155 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        58% Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

N-(4-Methoxy-2-nitrophenyl)acetamide

Crystal data

C9H10N2O4	F(000) = 440
Mr = 210.19	Dx = 1.510 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 14.8713 (7) Å	Cell parameters from 2102 reflections
b = 3.9563 (2) Å	θ = 3.3–66.3°
c = 17.2057 (9) Å	µ = 1.03 mm^−1
β = 114.051 (3)°	T = 90 K
V = 924.42 (8) Å^3	Lath, yellow
Z = 4	0.42 × 0.06 × 0.01 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer	1638 independent reflections
Radiation source: IµS microfocus	1211 reflections with I > 2σ(I)
QUAZAR multilayer optics monochromator	Rint = 0.122
φ and ω scans	θmax = 66.7°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→17
Tmin = 0.692, Tmax = 0.990	k = −4→4
11516 measured reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.203	w = 1/[σ^2(Fo^2) + 0.298P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1638 reflections	Δρmax = 0.24 e Å^−3
141 parameters	Δρmin = −0.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were located in difference maps and those on C were thereafter treated as riding in geometrically idealized positions with C—H distances 0.95 Å for phenyl and 0.98 Å for methyl. Coordinates of the N—H hydrogen atom were refined. U_iso(H) values were assigned as 1.2U_eq for the attached atom (1.5 for methyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58485 (18)	0.7604 (7)	0.81731 (16)	0.0512 (7)
O2	0.36866 (18)	0.2368 (6)	0.43490 (15)	0.0455 (6)
O3	0.23210 (18)	0.9412 (7)	0.67288 (16)	0.0529 (7)
O4	0.16683 (18)	0.9595 (6)	0.53559 (16)	0.0480 (7)
N1	0.4165 (2)	0.7462 (7)	0.75182 (18)	0.0447 (7)
H1N	0.363 (4)	0.830 (11)	0.753 (3)	0.054*
N2	0.2326 (2)	0.8718 (7)	0.60286 (18)	0.0416 (7)
C1	0.4018 (3)	0.6185 (9)	0.6716 (2)	0.0428 (8)
C2	0.3144 (2)	0.6751 (8)	0.5992 (2)	0.0420 (8)
C3	0.3005 (2)	0.5555 (8)	0.5182 (2)	0.0415 (8)
H3A	0.241073	0.602472	0.470197	0.050*
C4	0.3736 (3)	0.3699 (8)	0.5092 (2)	0.0417 (8)
C5	0.4605 (3)	0.3057 (8)	0.5806 (2)	0.0431 (8)
H5	0.511084	0.176401	0.574482	0.052*
C6	0.4740 (3)	0.4264 (9)	0.6593 (2)	0.0442 (8)
H6	0.533915	0.378381	0.706654	0.053*
C7	0.5054 (3)	0.8178 (8)	0.8187 (2)	0.0435 (8)
C8	0.4928 (3)	0.9743 (9)	0.8926 (2)	0.0475 (8)
H8A	0.473964	0.799894	0.923540	0.071*
H8B	0.441299	1.147414	0.872021	0.071*
H8C	0.554993	1.078496	0.930706	0.071*
C9	0.2843 (3)	0.3245 (9)	0.3589 (2)	0.0488 (9)
H9A	0.224837	0.228708	0.361637	0.073*
H9B	0.292327	0.233462	0.309172	0.073*
H9C	0.278101	0.571021	0.354165	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0331 (14)	0.0634 (15)	0.0497 (14)	0.0015 (10)	0.0093 (11)	−0.0066 (11)
O2	0.0413 (14)	0.0494 (13)	0.0439 (13)	−0.0005 (10)	0.0154 (10)	−0.0013 (10)
O3	0.0419 (14)	0.0706 (16)	0.0434 (14)	0.0026 (12)	0.0145 (11)	−0.0053 (11)
O4	0.0361 (13)	0.0553 (14)	0.0444 (13)	0.0047 (10)	0.0079 (10)	0.0026 (10)
N1	0.0398 (17)	0.0513 (16)	0.0424 (15)	0.0000 (12)	0.0162 (13)	0.0006 (12)
N2	0.0308 (15)	0.0463 (15)	0.0425 (16)	−0.0030 (11)	0.0097 (13)	−0.0028 (12)
C1	0.0376 (18)	0.0453 (17)	0.0429 (18)	−0.0019 (13)	0.0140 (15)	0.0030 (13)
C2	0.0354 (18)	0.0430 (17)	0.0458 (19)	−0.0024 (13)	0.0148 (15)	0.0032 (13)
C3	0.0342 (17)	0.0411 (17)	0.0432 (17)	−0.0037 (13)	0.0095 (14)	0.0033 (13)
C4	0.0381 (18)	0.0425 (17)	0.0446 (18)	−0.0025 (13)	0.0170 (15)	−0.0011 (13)
C5	0.0331 (18)	0.0454 (17)	0.0469 (19)	−0.0008 (13)	0.0125 (15)	−0.0009 (14)
C6	0.0366 (18)	0.0437 (17)	0.0495 (19)	0.0007 (13)	0.0146 (15)	0.0033 (14)
C7	0.0342 (19)	0.0449 (17)	0.0452 (18)	−0.0005 (13)	0.0099 (15)	0.0039 (13)
C8	0.0412 (19)	0.0501 (19)	0.0462 (18)	0.0005 (15)	0.0126 (15)	−0.0017 (15)
C9	0.045 (2)	0.0517 (19)	0.0416 (18)	0.0030 (15)	0.0089 (16)	−0.0008 (14)

Geometric parameters (Å, º)

O1—C7	1.214 (4)	C3—H3A	0.9500
O2—C4	1.357 (4)	C4—C5	1.395 (5)
O2—C9	1.438 (4)	C5—C6	1.371 (5)
O3—N2	1.239 (4)	C5—H5	0.9500
O4—N2	1.222 (4)	C6—H6	0.9500
N1—C7	1.383 (5)	C7—C8	1.492 (5)
N1—C1	1.401 (5)	C8—H8A	0.9800
N1—H1N	0.87 (5)	C8—H8B	0.9800
N2—C2	1.467 (4)	C8—H8C	0.9800
C1—C6	1.400 (5)	C9—H9A	0.9800
C1—C2	1.405 (5)	C9—H9B	0.9800
C2—C3	1.404 (5)	C9—H9C	0.9800
C3—C4	1.372 (5)
C4—O2—C9	117.1 (3)	C6—C5—H5	119.5
C7—N1—C1	127.4 (3)	C4—C5—H5	119.5
C7—N1—H1N	118 (3)	C5—C6—C1	121.7 (3)
C1—N1—H1N	113 (3)	C5—C6—H6	119.1
O4—N2—O3	122.6 (3)	C1—C6—H6	119.1
O4—N2—C2	117.9 (3)	O1—C7—N1	123.6 (3)
O3—N2—C2	119.6 (3)	O1—C7—C8	123.8 (3)
C6—C1—N1	121.6 (3)	N1—C7—C8	112.7 (3)
C6—C1—C2	116.2 (3)	C7—C8—H8A	109.5
N1—C1—C2	122.2 (3)	C7—C8—H8B	109.5
C3—C2—C1	122.4 (3)	H8A—C8—H8B	109.5
C3—C2—N2	115.6 (3)	C7—C8—H8C	109.5
C1—C2—N2	122.0 (3)	H8A—C8—H8C	109.5
C4—C3—C2	119.2 (3)	H8B—C8—H8C	109.5
C4—C3—H3A	120.4	O2—C9—H9A	109.5
C2—C3—H3A	120.4	O2—C9—H9B	109.5
O2—C4—C3	124.9 (3)	H9A—C9—H9B	109.5
O2—C4—C5	115.7 (3)	O2—C9—H9C	109.5
C3—C4—C5	119.4 (3)	H9A—C9—H9C	109.5
C6—C5—C4	121.0 (3)	H9B—C9—H9C	109.5
C7—N1—C1—C6	25.4 (5)	C9—O2—C4—C3	6.1 (5)
C7—N1—C1—C2	−154.6 (3)	C9—O2—C4—C5	−174.3 (3)
C6—C1—C2—C3	−1.8 (5)	C2—C3—C4—O2	179.1 (3)
N1—C1—C2—C3	178.2 (3)	C2—C3—C4—C5	−0.4 (5)
C6—C1—C2—N2	180.0 (3)	O2—C4—C5—C6	−179.9 (3)
N1—C1—C2—N2	−0.1 (5)	C3—C4—C5—C6	−0.3 (5)
O4—N2—C2—C3	−10.9 (4)	C4—C5—C6—C1	−0.1 (5)
O3—N2—C2—C3	168.8 (3)	N1—C1—C6—C5	−178.9 (3)
O4—N2—C2—C1	167.5 (3)	C2—C1—C6—C5	1.1 (5)
O3—N2—C2—C1	−12.8 (5)	C1—N1—C7—O1	−3.9 (6)
C1—C2—C3—C4	1.5 (5)	C1—N1—C7—C8	175.8 (3)
N2—C2—C3—C4	179.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.87 (5)	1.92 (5)	2.632 (4)	137 (4)
C5—H5···O2^i	0.95	2.48	3.418 (4)	171
C6—H6···O1	0.95	2.30	2.864 (4)	117
C8—H8B···O3^ii	0.98	2.64	3.578 (4)	160
C8—H8C···O4^iii	0.98	2.63	3.546 (4)	156

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x+1/2, −y+5/2, z+1/2.