4-Meth-oxy-N-(4-meth-oxy-2-nitro-phen-yl)benzamide.

In the title compound, C(15)H(14)N(2)O(5), the central amide C-C(=O)-N-C unit forms dihedral angles of 28.17 (13) and 26.47 (13)° with the two benzene rings, whereas the two benzene rings are almost coplanar, making a dihedral angle of 4.52 (13)°. The two meth-oxy and the nitro substituents are almost coplanar with their attached benzene rings, with C-O-C-C torsion angles of -1.3 (4) and -4.6 (4)°, and an O-N-C-C torsion angle of 17.1 (3)°. In the crystal, mol-ecules are linked via C-H⋯O and N-H⋯O inter-actions, forming a tape running along the b axis.

Related literature

For the crystal structures of related benzamide compounds, see: Sripet et al. (2012 ▶); Saeed et al. (2008 ▶); Saeed & Flörke (2009 ▶).

Experimental

Crystal data

C15H14N2O5

M = 302.28

Monoclinic,

a = 9.7206 (12) Å

b = 4.9885 (6) Å

c = 28.725 (4) Å

β = 95.628 (2)°

V = 1386.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.30 × 0.12 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.968, T max = 0.992

7491 measured reflections

2552 independent reflections

1638 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.155

S = 1.00

2552 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037701/is5189sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037701/is5189Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037701/is5189Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14N2O5	F(000) = 632
Mr = 302.28	Dx = 1.448 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 1456 reflections
a = 9.7206 (12) Å	θ = 2.3–28.0°
b = 4.9885 (6) Å	µ = 0.11 mm−1
c = 28.725 (4) Å	T = 273 K
β = 95.628 (2)°	Plate, colorles
V = 1386.2 (3) Å3	0.30 × 0.12 × 0.07 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2552 independent reflections
Radiation source: fine-focus sealed tube	1638 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→11
Tmin = 0.968, Tmax = 0.992	k = −6→6
7491 measured reflections	l = −34→34

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0824P)2] where P = (Fo2 + 2Fc2)/3
2552 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 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	−0.0633 (2)	0.6081 (4)	0.30064 (6)	0.0569 (6)
O2	0.0516 (2)	0.0858 (3)	0.10748 (7)	0.0621 (7)
O3	0.3257 (2)	0.4247 (4)	−0.08001 (6)	0.0560 (6)
O4	0.3544 (2)	0.8107 (5)	0.11160 (7)	0.0759 (8)
O5	0.4308 (2)	1.0026 (4)	0.05315 (7)	0.0629 (7)
N1	0.1306 (2)	0.5046 (4)	0.09575 (8)	0.0413 (6)
N2	0.3622 (2)	0.8309 (4)	0.06979 (8)	0.0415 (6)
C1	0.1170 (3)	0.6004 (5)	0.19444 (9)	0.0431 (7)
H1B	0.1889	0.6872	0.1815	0.052*
C2	0.0863 (3)	0.6723 (5)	0.23865 (9)	0.0465 (7)
H2A	0.1383	0.8033	0.2554	0.056*
C3	−0.0216 (3)	0.5495 (5)	0.25793 (9)	0.0415 (7)
C4	−0.0970 (3)	0.3527 (6)	0.23291 (9)	0.0508 (8)
H4A	−0.1709	0.2708	0.2456	0.061*
C5	−0.0633 (3)	0.2782 (5)	0.18956 (9)	0.0488 (8)
H5A	−0.1130	0.1415	0.1736	0.059*
C6	0.0434 (3)	0.4016 (4)	0.16870 (8)	0.0361 (6)
C7	0.0754 (3)	0.3157 (4)	0.12181 (8)	0.0368 (6)
C8	0.1817 (3)	0.4747 (4)	0.05195 (8)	0.0340 (6)
C9	0.2883 (3)	0.6356 (4)	0.03780 (8)	0.0329 (6)
C10	0.3324 (3)	0.6180 (5)	−0.00614 (8)	0.0381 (7)
H10A	0.4017	0.7313	−0.0146	0.046*
C11	0.2736 (3)	0.4317 (5)	−0.03782 (8)	0.0386 (7)
C12	0.1694 (3)	0.2690 (5)	−0.02481 (9)	0.0404 (7)
H12A	0.1297	0.1416	−0.0456	0.048*
C13	0.1236 (3)	0.2943 (5)	0.01899 (9)	0.0413 (7)
H13A	0.0511	0.1864	0.0266	0.050*
C14	0.2750 (3)	0.2204 (6)	−0.11201 (9)	0.0567 (8)
H14A	0.3227	0.2301	−0.1397	0.085*
H14B	0.1778	0.2458	−0.1202	0.085*
H14C	0.2905	0.0479	−0.0976	0.085*
C15	0.0108 (4)	0.8074 (6)	0.32821 (9)	0.0627 (9)
H15A	−0.0276	0.8246	0.3576	0.094*
H15B	0.0037	0.9758	0.3120	0.094*
H15C	0.1062	0.7563	0.3336	0.094*
H1A	0.138 (3)	0.648 (6)	0.1083 (9)	0.059 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0677 (16)	0.0606 (12)	0.0453 (11)	−0.0009 (11)	0.0196 (10)	−0.0054 (10)
O2	0.1059 (19)	0.0283 (9)	0.0559 (12)	−0.0171 (10)	0.0273 (11)	−0.0071 (9)
O3	0.0702 (16)	0.0543 (11)	0.0473 (11)	−0.0215 (10)	0.0250 (10)	−0.0120 (9)
O4	0.085 (2)	0.0929 (16)	0.0514 (13)	−0.0457 (14)	0.0168 (11)	−0.0209 (12)
O5	0.0706 (17)	0.0463 (11)	0.0716 (14)	−0.0343 (11)	0.0066 (11)	0.0025 (10)
N1	0.0570 (18)	0.0242 (11)	0.0452 (13)	−0.0096 (10)	0.0184 (11)	−0.0070 (10)
N2	0.0403 (16)	0.0338 (11)	0.0504 (14)	−0.0078 (10)	0.0051 (11)	−0.0041 (11)
C1	0.0422 (19)	0.0399 (14)	0.0492 (16)	−0.0091 (13)	0.0147 (13)	−0.0034 (13)
C2	0.056 (2)	0.0392 (14)	0.0449 (15)	−0.0088 (13)	0.0094 (14)	−0.0082 (13)
C3	0.046 (2)	0.0384 (14)	0.0413 (15)	0.0061 (13)	0.0110 (13)	0.0037 (12)
C4	0.049 (2)	0.0525 (16)	0.0533 (17)	−0.0147 (14)	0.0177 (14)	0.0016 (14)
C5	0.057 (2)	0.0408 (14)	0.0493 (16)	−0.0179 (14)	0.0113 (14)	−0.0033 (13)
C6	0.0405 (18)	0.0255 (11)	0.0432 (14)	−0.0013 (11)	0.0083 (12)	0.0005 (11)
C7	0.0398 (18)	0.0256 (12)	0.0457 (14)	−0.0004 (11)	0.0085 (12)	−0.0031 (11)
C8	0.0384 (18)	0.0248 (11)	0.0400 (14)	−0.0019 (11)	0.0110 (12)	0.0002 (10)
C9	0.0321 (17)	0.0226 (11)	0.0438 (14)	−0.0023 (10)	0.0026 (12)	−0.0019 (10)
C10	0.0377 (18)	0.0307 (12)	0.0477 (15)	−0.0057 (12)	0.0126 (12)	0.0034 (11)
C11	0.0444 (19)	0.0325 (12)	0.0405 (14)	0.0013 (12)	0.0122 (12)	−0.0002 (11)
C12	0.0469 (19)	0.0299 (12)	0.0454 (15)	−0.0085 (12)	0.0100 (13)	−0.0080 (11)
C13	0.0434 (19)	0.0334 (12)	0.0488 (15)	−0.0147 (12)	0.0127 (13)	−0.0068 (12)
C14	0.068 (2)	0.0585 (18)	0.0457 (16)	−0.0103 (16)	0.0147 (15)	−0.0122 (14)
C15	0.097 (3)	0.0487 (16)	0.0445 (16)	0.0080 (17)	0.0159 (17)	−0.0035 (14)

O1—C3	1.361 (3)	C5—C6	1.391 (4)
O1—C15	1.422 (3)	C5—H5A	0.9300
O2—C7	1.232 (3)	C6—C7	1.475 (3)
O3—C11	1.359 (3)	C8—C13	1.386 (3)
O3—C14	1.427 (3)	C8—C9	1.402 (3)
O4—N2	1.215 (3)	C9—C10	1.375 (3)
O5—N2	1.212 (3)	C10—C11	1.384 (3)
N1—C7	1.348 (3)	C10—H10A	0.9300
N1—C8	1.405 (3)	C11—C12	1.378 (4)
N1—H1A	0.80 (3)	C12—C13	1.381 (3)
N2—C9	1.476 (3)	C12—H12A	0.9300
C1—C2	1.380 (3)	C13—H13A	0.9300
C1—C6	1.392 (3)	C14—H14A	0.9600
C1—H1B	0.9300	C14—H14B	0.9600
C2—C3	1.377 (4)	C14—H14C	0.9600
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.384 (4)	C15—H15B	0.9600
C4—C5	1.370 (4)	C15—H15C	0.9600
C4—H4A	0.9300
C3—O1—C15	118.2 (2)	C13—C8—N1	121.6 (2)
C11—O3—C14	117.2 (2)	C9—C8—N1	122.3 (2)
C7—N1—C8	128.2 (2)	C10—C9—C8	122.4 (2)
C7—N1—H1A	113 (2)	C10—C9—N2	116.0 (2)
C8—N1—H1A	118 (2)	C8—C9—N2	121.7 (2)
O5—N2—O4	122.6 (2)	C9—C10—C11	120.1 (2)
O5—N2—C9	118.2 (2)	C9—C10—H10A	120.0
O4—N2—C9	119.2 (2)	C11—C10—H10A	120.0
C2—C1—C6	121.8 (3)	O3—C11—C12	125.1 (2)
C2—C1—H1B	119.1	O3—C11—C10	116.0 (2)
C6—C1—H1B	119.1	C12—C11—C10	118.9 (2)
C3—C2—C1	119.8 (2)	C11—C12—C13	120.3 (2)
C3—C2—H2A	120.1	C11—C12—H12A	119.9
C1—C2—H2A	120.1	C13—C12—H12A	119.9
O1—C3—C2	125.0 (2)	C12—C13—C8	122.4 (2)
O1—C3—C4	115.5 (3)	C12—C13—H13A	118.8
C2—C3—C4	119.5 (2)	C8—C13—H13A	118.8
C5—C4—C3	120.2 (3)	O3—C14—H14A	109.5
C5—C4—H4A	119.9	O3—C14—H14B	109.5
C3—C4—H4A	119.9	H14A—C14—H14B	109.5
C4—C5—C6	121.8 (2)	O3—C14—H14C	109.5
C4—C5—H5A	119.1	H14A—C14—H14C	109.5
C6—C5—H5A	119.1	H14B—C14—H14C	109.5
C5—C6—C1	116.9 (2)	O1—C15—H15A	109.5
C5—C6—C7	119.8 (2)	O1—C15—H15B	109.5
C1—C6—C7	123.3 (2)	H15A—C15—H15B	109.5
O2—C7—N1	122.5 (2)	O1—C15—H15C	109.5
O2—C7—C6	121.7 (2)	H15A—C15—H15C	109.5
N1—C7—C6	115.8 (2)	H15B—C15—H15C	109.5
C13—C8—C9	115.9 (2)
C6—C1—C2—C3	−1.3 (4)	C13—C8—C9—C10	0.4 (4)
C15—O1—C3—C2	−1.3 (4)	N1—C8—C9—C10	−175.8 (2)
C15—O1—C3—C4	179.6 (2)	C13—C8—C9—N2	−178.2 (2)
C1—C2—C3—O1	−178.4 (2)	N1—C8—C9—N2	5.6 (4)
C1—C2—C3—C4	0.7 (4)	O5—N2—C9—C10	17.1 (3)
O1—C3—C4—C5	−179.8 (2)	O4—N2—C9—C10	−161.4 (2)
C2—C3—C4—C5	0.9 (4)	O5—N2—C9—C8	−164.2 (2)
C3—C4—C5—C6	−2.1 (4)	O4—N2—C9—C8	17.4 (4)
C4—C5—C6—C1	1.6 (4)	C8—C9—C10—C11	−1.7 (4)
C4—C5—C6—C7	−179.6 (2)	N2—C9—C10—C11	177.0 (2)
C2—C1—C6—C5	0.2 (4)	C14—O3—C11—C12	−4.6 (4)
C2—C1—C6—C7	−178.6 (2)	C14—O3—C11—C10	175.1 (2)
C8—N1—C7—O2	−6.6 (4)	C9—C10—C11—O3	−178.6 (2)
C8—N1—C7—C6	174.1 (2)	C9—C10—C11—C12	1.1 (4)
C5—C6—C7—O2	−27.8 (4)	O3—C11—C12—C13	−179.6 (2)
C1—C6—C7—O2	150.9 (3)	C10—C11—C12—C13	0.7 (4)
C5—C6—C7—N1	151.5 (3)	C11—C12—C13—C8	−2.1 (4)
C1—C6—C7—N1	−29.7 (4)	C9—C8—C13—C12	1.5 (4)
C7—N1—C8—C13	33.7 (4)	N1—C8—C13—C12	177.7 (2)
C7—N1—C8—C9	−150.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.80 (3)	2.34 (3)	3.027 (3)	145 (3)
C10—H10A···O5ii	0.93	2.45	3.364 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.80 (3)	2.34 (3)	3.027 (3)	145 (3)
C10—H10A⋯O5ii	0.93	2.45	3.364 (3)	168

Symmetry codes: (i) ; (ii) .