Methyl 2-(3,5-dinitro-benzamido)-3-methyl-butano-ate.

In the title compound, C(13)H(15)N(3)O(7), the dihedral angle between the amide plane (r.m.s. deviation = 0.008 Å) and the benzene ring is 33.2 (2)°. In the crystal, mol-ecules are connected by N-H⋯O=C hydrogen bonds, forming a chain along the b-axis direction.

Related literature

For the biological activity of related compounds, see: Sykes et al. (1999 ▶).

Experimental

Crystal data

C13H15N3O7

M = 325.28

Orthorhombic,

a = 7.060 (2) Å

b = 9.412 (3) Å

c = 23.321 (6) Å

V = 1549.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.43 × 0.32 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.660, T max = 0.746

9197 measured reflections

3580 independent reflections

3003 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.131

S = 1.03

3580 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040895/kp2434sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040895/kp2434Isup2.hkl

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

C13H15N3O7	F(000) = 680
Mr = 325.28	Dx = 1.394 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9233 reflections
a = 7.060 (2) Å	θ = 1.0–22.7°
b = 9.412 (3) Å	µ = 0.12 mm−1
c = 23.321 (6) Å	T = 296 K
V = 1549.8 (7) Å3	Block, colourless
Z = 4	0.43 × 0.32 × 0.30 mm

Bruker APEXII CCD area-detector diffractometer	3580 independent reflections
Radiation source: fine-focus sealed tube	3003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
phi and ω scans	θmax = 27.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.660, Tmax = 0.746	k = −12→12
9197 measured reflections	l = −26→30

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0802P)2 + 0.1123P] where P = (Fo2 + 2Fc2)/3
3580 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 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. C10, C11, C13 and C12 belong to terminal alkyl chains which show signs of disorder and have higher thermal parameters.

	x	y	z	Uiso*/Ueq
C1	1.2857 (3)	0.28856 (19)	0.10037 (8)	0.0526 (4)
C2	1.2504 (3)	0.23672 (19)	0.15455 (8)	0.0503 (4)
H2A	1.3390	0.1801	0.1732	0.060*
C3	1.0795 (2)	0.27084 (17)	0.18071 (7)	0.0453 (4)
C4	0.9487 (3)	0.35376 (18)	0.15216 (8)	0.0469 (4)
H4A	0.8350	0.3785	0.1696	0.056*
C5	0.9895 (3)	0.39948 (18)	0.09717 (7)	0.0495 (4)
C6	1.1576 (3)	0.3692 (2)	0.07014 (8)	0.0521 (4)
H6A	1.1834	0.4015	0.0333	0.062*
C7	1.0425 (2)	0.21140 (17)	0.23943 (7)	0.0460 (4)
C8	0.8869 (3)	0.2398 (2)	0.33103 (8)	0.0557 (4)
H8A	0.9465	0.1466	0.3358	0.067*
C9	0.9790 (4)	0.3399 (3)	0.37526 (9)	0.0671 (6)
C10	0.5694 (5)	0.3567 (4)	0.3394 (2)	0.1160 (12)
H15A	0.4365	0.3390	0.3442	0.174*
H15B	0.5902	0.4049	0.3036	0.174*
H15C	0.6142	0.4149	0.3703	0.174*
C11	0.5992 (4)	0.1150 (4)	0.29434 (14)	0.0947 (9)
H14A	0.4656	0.1019	0.2998	0.142*
H14B	0.6627	0.0253	0.2983	0.142*
H14C	0.6221	0.1526	0.2567	0.142*
C12	1.0720 (6)	0.3594 (4)	0.47134 (13)	0.1166 (13)
H12A	1.0668	0.3069	0.5066	0.175*
H12B	1.0072	0.4483	0.4760	0.175*
H12C	1.2018	0.3769	0.4613	0.175*
C13	0.6744 (4)	0.2186 (3)	0.33924 (11)	0.0735 (6)
H13A	0.6560	0.1746	0.3769	0.088*
N1	1.4675 (3)	0.2555 (2)	0.07277 (9)	0.0671 (5)
N2	0.8475 (3)	0.48375 (18)	0.06597 (7)	0.0613 (4)
N5	0.9379 (2)	0.29050 (15)	0.27435 (6)	0.0506 (4)
H5A	0.9000	0.3728	0.2632	0.061*
O1	1.5804 (3)	0.1847 (3)	0.09906 (10)	0.0990 (6)
O2	1.4962 (3)	0.3026 (2)	0.02520 (8)	0.0877 (6)
O3	0.8739 (3)	0.5050 (2)	0.01510 (7)	0.0856 (5)
O4	0.7125 (3)	0.5274 (2)	0.09269 (7)	0.0781 (5)
O5	1.1072 (2)	0.09485 (13)	0.25244 (6)	0.0596 (4)
O6	0.9809 (3)	0.2774 (2)	0.42582 (6)	0.0897 (6)
O7	1.0395 (5)	0.4534 (3)	0.36573 (10)	0.1163 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0540 (10)	0.0489 (9)	0.0547 (10)	−0.0103 (8)	0.0075 (8)	−0.0126 (8)
C2	0.0526 (9)	0.0426 (8)	0.0556 (10)	−0.0011 (7)	−0.0013 (8)	−0.0040 (7)
C3	0.0525 (9)	0.0375 (7)	0.0460 (8)	−0.0054 (7)	−0.0006 (7)	−0.0030 (7)
C4	0.0503 (9)	0.0439 (8)	0.0464 (8)	−0.0035 (7)	−0.0001 (7)	−0.0047 (7)
C5	0.0614 (10)	0.0427 (8)	0.0445 (8)	−0.0027 (8)	−0.0047 (8)	−0.0028 (7)
C6	0.0639 (11)	0.0497 (9)	0.0426 (8)	−0.0102 (8)	0.0046 (8)	−0.0043 (7)
C7	0.0500 (9)	0.0402 (8)	0.0477 (8)	−0.0039 (7)	−0.0024 (7)	0.0004 (7)
C8	0.0658 (11)	0.0549 (10)	0.0463 (9)	0.0091 (9)	0.0023 (8)	0.0045 (8)
C9	0.0770 (14)	0.0720 (13)	0.0523 (11)	0.0169 (12)	−0.0047 (10)	−0.0061 (9)
C10	0.0821 (19)	0.094 (2)	0.172 (4)	0.0177 (17)	0.034 (2)	0.017 (2)
C11	0.0834 (18)	0.099 (2)	0.102 (2)	−0.0206 (17)	−0.0107 (15)	0.0137 (17)
C12	0.152 (3)	0.130 (3)	0.0680 (16)	0.019 (3)	−0.0295 (19)	−0.0348 (17)
C13	0.0736 (14)	0.0762 (14)	0.0707 (13)	−0.0033 (12)	0.0113 (11)	0.0167 (11)
N1	0.0613 (10)	0.0632 (10)	0.0769 (12)	−0.0070 (9)	0.0174 (9)	−0.0107 (9)
N2	0.0743 (11)	0.0594 (9)	0.0504 (9)	0.0028 (9)	−0.0069 (8)	0.0018 (7)
N5	0.0629 (9)	0.0432 (7)	0.0456 (7)	0.0071 (7)	0.0047 (6)	0.0055 (6)
O1	0.0641 (10)	0.1110 (14)	0.1218 (16)	0.0183 (11)	0.0206 (10)	0.0107 (13)
O2	0.0948 (13)	0.0910 (12)	0.0773 (11)	−0.0046 (11)	0.0372 (10)	−0.0117 (9)
O3	0.1103 (15)	0.0954 (12)	0.0511 (8)	0.0146 (12)	−0.0049 (9)	0.0146 (8)
O4	0.0800 (11)	0.0881 (11)	0.0661 (9)	0.0258 (9)	−0.0040 (8)	0.0041 (8)
O5	0.0776 (9)	0.0431 (6)	0.0580 (7)	0.0098 (6)	0.0016 (7)	0.0035 (6)
O6	0.1274 (15)	0.0904 (11)	0.0512 (8)	0.0167 (12)	−0.0109 (9)	−0.0112 (8)
O7	0.162 (2)	0.0923 (13)	0.0946 (14)	−0.0369 (15)	−0.0343 (14)	−0.0015 (12)

C1—C6	1.375 (3)	C9—O6	1.318 (3)
C1—C2	1.377 (3)	C10—C13	1.497 (4)
C1—N1	1.469 (3)	C10—H15A	0.9600
C2—C3	1.390 (3)	C10—H15B	0.9600
C2—H2A	0.9300	C10—H15C	0.9600
C3—C4	1.380 (3)	C11—C13	1.526 (4)
C3—C7	1.502 (2)	C11—H14A	0.9600
C4—C5	1.383 (3)	C11—H14B	0.9600
C4—H4A	0.9300	C11—H14C	0.9600
C5—C6	1.373 (3)	C12—O6	1.462 (3)
C5—N2	1.471 (3)	C12—H12A	0.9600
C6—H6A	0.9300	C12—H12B	0.9600
C7—O5	1.226 (2)	C12—H12C	0.9600
C7—N5	1.328 (2)	C13—H13A	0.9800
C8—N5	1.451 (2)	N1—O1	1.206 (3)
C8—C13	1.525 (3)	N1—O2	1.212 (3)
C8—C9	1.541 (3)	N2—O4	1.211 (2)
C8—H8A	0.9800	N2—O3	1.217 (2)
C9—O7	1.171 (3)	N5—H5A	0.8600
C6—C1—C2	123.15 (18)	H15A—C10—H15B	109.5
C6—C1—N1	117.83 (18)	C13—C10—H15C	109.5
C2—C1—N1	119.02 (19)	H15A—C10—H15C	109.5
C1—C2—C3	118.55 (18)	H15B—C10—H15C	109.5
C1—C2—H2A	120.7	C13—C11—H14A	109.5
C3—C2—H2A	120.7	C13—C11—H14B	109.5
C4—C3—C2	119.99 (17)	H14A—C11—H14B	109.5
C4—C3—C7	122.29 (16)	C13—C11—H14C	109.5
C2—C3—C7	117.70 (16)	H14A—C11—H14C	109.5
C3—C4—C5	118.94 (17)	H14B—C11—H14C	109.5
C3—C4—H4A	120.5	O6—C12—H12A	109.5
C5—C4—H4A	120.5	O6—C12—H12B	109.5
C6—C5—C4	122.75 (17)	H12A—C12—H12B	109.5
C6—C5—N2	118.28 (16)	O6—C12—H12C	109.5
C4—C5—N2	118.97 (17)	H12A—C12—H12C	109.5
C5—C6—C1	116.59 (17)	H12B—C12—H12C	109.5
C5—C6—H6A	121.7	C10—C13—C8	111.9 (2)
C1—C6—H6A	121.7	C10—C13—C11	112.6 (3)
O5—C7—N5	123.84 (16)	C8—C13—C11	109.9 (2)
O5—C7—C3	119.61 (16)	C10—C13—H13A	107.4
N5—C7—C3	116.54 (14)	C8—C13—H13A	107.4
N5—C8—C13	113.70 (18)	C11—C13—H13A	107.4
N5—C8—C9	107.70 (17)	O1—N1—O2	123.8 (2)
C13—C8—C9	114.29 (18)	O1—N1—C1	118.12 (19)
N5—C8—H8A	106.9	O2—N1—C1	118.0 (2)
C13—C8—H8A	106.9	O4—N2—O3	124.5 (2)
C9—C8—H8A	106.9	O4—N2—C5	117.71 (17)
O7—C9—O6	125.0 (2)	O3—N2—C5	117.81 (19)
O7—C9—C8	125.7 (2)	C7—N5—C8	120.85 (15)
O6—C9—C8	109.3 (2)	C7—N5—H5A	119.6
C13—C10—H15A	109.5	C8—N5—H5A	119.6
C13—C10—H15B	109.5	C9—O6—C12	114.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O5i	0.86	2.12	2.949 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O5i	0.86	2.12	2.949 (2)	161

Symmetry code: (i) .