(R*)-Methyl 2-(2,6-dimeth-oxy-3,5-di-nitro-benzamido)-propano-ate.

In the title mol-ecule, C(13)H(15)N(3)O(9), the nitro groups are tilted with respect to the benzene mean plane by 22.8 (3) and 31.6 (3)°. The meth-oxy groups are in a cis orientation relative to the ring. In the crystal, mol-ecules are linked by strong N-H⋯O hydrogen bonds into C(3) chains along [100].

Related literature

For the biological activity of related compounds or for their use as prodrugs, see: Sykes et al. (1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H15N3O9

M = 357.28

Orthorhombic,

a = 4.6933 (10) Å

b = 17.501 (3) Å

c = 19.917 (4) Å

V = 1635.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.31 × 0.30 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.989

9526 measured reflections

3683 independent reflections

2824 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.153

S = 1.03

3683 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 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: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029935/bx2416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029935/bx2416Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029935/bx2416Isup3.cml

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

C13H15N3O9	Dx = 1.451 Mg m−3
Mr = 357.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9565 reflections
a = 4.6933 (10) Å	θ = 1.0–27.5°
b = 17.501 (3) Å	µ = 0.13 mm−1
c = 19.917 (4) Å	T = 296 K
V = 1635.9 (6) Å3	Block, yellow
Z = 4	0.31 × 0.30 × 0.09 mm
F(000) = 744

Bruker APEXII CCD area-detector diffractometer	3683 independent reflections
Radiation source: fine-focus sealed tube	2824 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
Tmin = 0.962, Tmax = 0.989	k = −22→15
9526 measured reflections	l = −25→25

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) = 0.153	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3683 reflections	(Δ/σ)max = 0.002
226 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.17 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
C1	0.7640 (5)	1.00166 (13)	0.58894 (9)	0.0458 (5)
H1A	0.8771	1.0043	0.6272	0.055*
C2	0.6630 (5)	1.06770 (14)	0.56054 (9)	0.0443 (5)
C3	0.4986 (5)	1.06566 (13)	0.50149 (9)	0.0415 (5)
C4	0.4388 (4)	0.99479 (13)	0.47345 (9)	0.0376 (4)
C5	0.5350 (5)	0.92644 (13)	0.50238 (10)	0.0412 (5)
C6	0.6998 (5)	0.93146 (13)	0.56147 (9)	0.0424 (5)
C7	0.6194 (8)	1.17734 (18)	0.44049 (16)	0.0750 (9)
H7A	0.5299	1.2192	0.4176	0.113*
H7B	0.7360	1.1493	0.4095	0.113*
H7C	0.7360	1.1967	0.4763	0.113*
C8	0.0896 (12)	1.1761 (2)	0.26985 (16)	0.1048 (14)
H8A	0.1719	1.2205	0.2905	0.157*
H8B	−0.1055	1.1712	0.2836	0.157*
H8C	0.0984	1.1813	0.2219	0.157*
C9	0.6995 (7)	0.81397 (17)	0.44691 (14)	0.0634 (7)
H9A	0.6247	0.7695	0.4248	0.095*
H9B	0.8128	0.7985	0.4847	0.095*
H9C	0.8154	0.8424	0.4160	0.095*
C10	0.3449 (5)	0.97587 (18)	0.28526 (10)	0.0609 (7)
H10A	0.5105	0.9771	0.2553	0.073*
C11	0.1574 (6)	1.04345 (19)	0.26521 (11)	0.0605 (7)
C12	0.2859 (4)	0.99044 (13)	0.40660 (10)	0.0414 (5)
C13	0.2023 (7)	0.8995 (2)	0.27420 (14)	0.0836 (10)
H13A	0.3295	0.8592	0.2875	0.125*
H13B	0.1556	0.8938	0.2275	0.125*
H13C	0.0314	0.8968	0.3006	0.125*
N1	0.7169 (6)	1.13899 (13)	0.59792 (10)	0.0603 (6)
N2	0.7960 (5)	0.86403 (13)	0.59826 (9)	0.0540 (5)
N3	0.4560 (4)	0.98513 (13)	0.35366 (8)	0.0513 (5)
H3A	0.6373	0.9872	0.3596	0.062*
O1	−0.0446 (5)	1.03749 (15)	0.22813 (10)	0.0861 (7)
O2	0.0251 (3)	0.99289 (11)	0.40308 (7)	0.0561 (5)
O3	0.2451 (5)	1.10947 (14)	0.29000 (8)	0.0787 (6)
O4	0.4046 (4)	1.12770 (10)	0.46763 (8)	0.0550 (5)
O5	0.4680 (4)	0.86110 (9)	0.46968 (8)	0.0529 (4)
O6	0.9142 (7)	1.13948 (14)	0.63661 (12)	0.1064 (10)
O7	0.5635 (7)	1.19271 (14)	0.58904 (12)	0.0949 (8)
O8	1.0181 (5)	0.87020 (14)	0.63012 (10)	0.0811 (7)
O9	0.6518 (5)	0.80595 (12)	0.59661 (10)	0.0734 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0423 (11)	0.0649 (13)	0.0303 (8)	−0.0062 (11)	−0.0056 (8)	0.0043 (10)
C2	0.0437 (11)	0.0547 (13)	0.0345 (9)	−0.0068 (10)	−0.0009 (9)	−0.0023 (9)
C3	0.0314 (10)	0.0576 (13)	0.0354 (9)	−0.0007 (10)	0.0013 (9)	0.0037 (9)
C4	0.0228 (8)	0.0588 (12)	0.0310 (8)	0.0009 (9)	0.0004 (7)	0.0008 (9)
C5	0.0260 (9)	0.0566 (13)	0.0410 (10)	−0.0022 (9)	0.0015 (9)	−0.0031 (9)
C6	0.0336 (11)	0.0581 (13)	0.0354 (9)	0.0022 (10)	0.0008 (9)	0.0048 (9)
C7	0.078 (2)	0.0735 (19)	0.0740 (17)	0.0061 (16)	0.0089 (16)	0.0259 (14)
C8	0.129 (4)	0.123 (3)	0.0616 (17)	0.032 (3)	−0.001 (2)	0.0052 (19)
C9	0.0620 (18)	0.0638 (16)	0.0644 (14)	0.0038 (13)	0.0064 (14)	−0.0134 (12)
C10	0.0324 (11)	0.118 (2)	0.0326 (9)	−0.0047 (13)	0.0007 (9)	−0.0132 (12)
C11	0.0410 (12)	0.110 (2)	0.0305 (9)	−0.0086 (14)	−0.0010 (10)	0.0026 (12)
C12	0.0239 (10)	0.0637 (14)	0.0365 (9)	−0.0017 (9)	−0.0035 (7)	−0.0036 (10)
C13	0.068 (2)	0.125 (3)	0.0582 (15)	−0.001 (2)	−0.0094 (16)	−0.0271 (17)
N1	0.0736 (16)	0.0621 (14)	0.0453 (10)	−0.0049 (12)	−0.0063 (12)	−0.0047 (10)
N2	0.0506 (12)	0.0682 (14)	0.0431 (10)	0.0058 (11)	−0.0007 (10)	0.0072 (9)
N3	0.0228 (8)	0.0949 (15)	0.0361 (8)	−0.0030 (9)	−0.0030 (7)	−0.0052 (9)
O1	0.0594 (12)	0.1340 (19)	0.0649 (11)	−0.0156 (13)	−0.0300 (11)	0.0121 (12)
O2	0.0222 (7)	0.1020 (13)	0.0441 (7)	−0.0014 (8)	−0.0028 (6)	−0.0035 (9)
O3	0.0758 (14)	0.1116 (17)	0.0487 (9)	0.0014 (14)	−0.0148 (10)	−0.0017 (10)
O4	0.0494 (10)	0.0585 (10)	0.0571 (9)	0.0025 (7)	−0.0093 (8)	0.0101 (8)
O5	0.0432 (9)	0.0580 (9)	0.0576 (9)	−0.0037 (8)	−0.0076 (8)	−0.0111 (7)
O6	0.139 (3)	0.0824 (15)	0.0981 (15)	−0.0124 (16)	−0.0724 (18)	−0.0102 (12)
O7	0.110 (2)	0.0825 (15)	0.0920 (14)	0.0233 (15)	−0.0242 (16)	−0.0324 (12)
O8	0.0694 (14)	0.0956 (15)	0.0782 (13)	0.0171 (12)	−0.0322 (12)	0.0102 (11)
O9	0.0795 (14)	0.0658 (12)	0.0747 (12)	−0.0045 (11)	−0.0042 (11)	0.0178 (10)

C1—C2	1.371 (3)	C9—O5	1.438 (3)
C1—C6	1.378 (3)	C9—H9A	0.9600
C1—H1A	0.9300	C9—H9B	0.9600
C2—C3	1.407 (3)	C9—H9C	0.9600
C2—N1	1.475 (3)	C10—N3	1.468 (3)
C3—O4	1.352 (3)	C10—C13	1.512 (5)
C3—C4	1.389 (3)	C10—C11	1.527 (4)
C4—C5	1.402 (3)	C10—H10A	0.9800
C4—C12	1.514 (3)	C11—O1	1.207 (3)
C5—O5	1.353 (3)	C11—O3	1.322 (4)
C5—C6	1.411 (3)	C12—O2	1.227 (2)
C6—N2	1.461 (3)	C12—N3	1.326 (3)
C7—O4	1.436 (4)	C13—H13A	0.9600
C7—H7A	0.9600	C13—H13B	0.9600
C7—H7B	0.9600	C13—H13C	0.9600
C7—H7C	0.9600	N1—O7	1.197 (3)
C8—O3	1.433 (4)	N1—O6	1.205 (3)
C8—H8A	0.9600	N2—O9	1.222 (3)
C8—H8B	0.9600	N2—O8	1.225 (3)
C8—H8C	0.9600	N3—H3A	0.8600
C2—C1—C6	120.80 (18)	O5—C9—H9C	109.5
C2—C1—H1A	119.6	H9A—C9—H9C	109.5
C6—C1—H1A	119.6	H9B—C9—H9C	109.5
C1—C2—C3	120.86 (19)	N3—C10—C13	113.0 (2)
C1—C2—N1	116.46 (19)	N3—C10—C11	111.2 (2)
C3—C2—N1	122.5 (2)	C13—C10—C11	113.1 (2)
O4—C3—C4	116.79 (17)	N3—C10—H10A	106.3
O4—C3—C2	125.1 (2)	C13—C10—H10A	106.3
C4—C3—C2	118.00 (18)	C11—C10—H10A	106.3
C3—C4—C5	122.10 (17)	O1—C11—O3	123.3 (3)
C3—C4—C12	119.61 (18)	O1—C11—C10	123.1 (3)
C5—C4—C12	118.10 (19)	O3—C11—C10	113.6 (2)
O5—C5—C4	116.62 (18)	O2—C12—N3	123.90 (18)
O5—C5—C6	125.6 (2)	O2—C12—C4	121.40 (18)
C4—C5—C6	117.79 (19)	N3—C12—C4	114.68 (16)
C1—C6—C5	120.4 (2)	C10—C13—H13A	109.5
C1—C6—N2	116.97 (18)	C10—C13—H13B	109.5
C5—C6—N2	122.5 (2)	H13A—C13—H13B	109.5
O4—C7—H7A	109.5	C10—C13—H13C	109.5
O4—C7—H7B	109.5	H13A—C13—H13C	109.5
H7A—C7—H7B	109.5	H13B—C13—H13C	109.5
O4—C7—H7C	109.5	O7—N1—O6	123.4 (2)
H7A—C7—H7C	109.5	O7—N1—C2	119.1 (2)
H7B—C7—H7C	109.5	O6—N1—C2	117.4 (2)
O3—C8—H8A	109.5	O9—N2—O8	124.0 (2)
O3—C8—H8B	109.5	O9—N2—C6	119.2 (2)
H8A—C8—H8B	109.5	O8—N2—C6	116.8 (2)
O3—C8—H8C	109.5	C12—N3—C10	122.15 (17)
H8A—C8—H8C	109.5	C12—N3—H3A	118.9
H8B—C8—H8C	109.5	C10—N3—H3A	118.9
O5—C9—H9A	109.5	C11—O3—C8	116.6 (3)
O5—C9—H9B	109.5	C3—O4—C7	116.4 (2)
H9A—C9—H9B	109.5	C5—O5—C9	117.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.86	2.02	2.850 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.86	2.02	2.850 (2)	162

Symmetry code: (i) .