Methyl 2-(4-chloro-3,5-dinitro-benz-amido)-acetate.

The title mol-ecule, C(10)H(8)ClN(3)O(7), is twisted with the dihedral angle between the amide and benzene ring being 38.75 (11)°. The C-N-C-C torsion angle between the amide and acetyl groups is -150.1 (2)°. Finally, each nitro group is twisted out of the plane of the benzene ring to which it is connected [O-N-C-C torsion angles = 34.0 (3) and -64.5 (3)°]. Linear supra-molecular chains along [010] and mediated by N-H⋯O hydrogen bonds between successive amide groups dominate the crystal packing. The chains are consolidated into the three-dimensional structure by C-H⋯O contacts.

Related literature

For biological and crystal engineering studies of related compounds, see: Liu et al. (2009 ▶); Eissmann & Weber (2011 ▶).

Experimental

Crystal data

C10H8ClN3O7

M = 317.64

Orthorhombic,

a = 14.5219 (5) Å

b = 4.7949 (2) Å

c = 18.5368 (6) Å

V = 1290.74 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.906, T max = 0.967

4743 measured reflections

2258 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.074

S = 1.08

2258 reflections

194 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 725 Friedel pairs

Flack parameter: −0.05 (6)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050446/hg5145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050446/hg5145Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050446/hg5145Isup3.cml

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

C10H8ClN3O7	F(000) = 648
Mr = 317.64	Dx = 1.635 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2633 reflections
a = 14.5219 (5) Å	θ = 2.6–27.5°
b = 4.7949 (2) Å	µ = 0.34 mm−1
c = 18.5368 (6) Å	T = 100 K
V = 1290.74 (8) Å3	Prism, yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Agilent SuperNova Dual diffractometer with Atlas detector	2258 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2134 reflections with I > 2σ(I)
Mirror	Rint = 0.030
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.8°
ω scan	h = −13→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −6→5
Tmin = 0.906, Tmax = 0.967	l = −17→24
4743 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0367P)2 + 0.1422P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2258 reflections	Δρmax = 0.22 e Å−3
194 parameters	Δρmin = −0.25 e Å−3
2 restraints	Absolute structure: Flack (1983), 725 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (6)

	x	y	z	Uiso*/Ueq
Cl1	0.97666 (4)	0.68297 (13)	0.49982 (3)	0.02449 (14)
O1	0.46196 (11)	0.5789 (4)	0.87399 (9)	0.0214 (4)
O2	0.51448 (12)	0.8605 (3)	0.78629 (9)	0.0232 (4)
O3	0.73214 (11)	0.1135 (3)	0.76810 (9)	0.0212 (4)
O4	1.03518 (12)	0.0525 (4)	0.65033 (11)	0.0278 (4)
O5	1.09547 (11)	0.4311 (4)	0.60728 (11)	0.0282 (4)
O6	0.81733 (12)	1.0984 (3)	0.50745 (10)	0.0286 (4)
O7	0.71827 (12)	0.7754 (4)	0.48417 (10)	0.0329 (5)
N1	0.67321 (13)	0.5506 (4)	0.77382 (11)	0.0154 (4)
N2	1.03014 (12)	0.2929 (4)	0.62781 (11)	0.0188 (4)
N3	0.78247 (13)	0.8709 (4)	0.51797 (10)	0.0179 (4)
C1	0.37848 (17)	0.7447 (6)	0.87927 (14)	0.0260 (5)
H1A	0.3379	0.6641	0.9160	0.039*
H1B	0.3469	0.7454	0.8326	0.039*
H1C	0.3944	0.9363	0.8928	0.039*
C2	0.52388 (15)	0.6648 (5)	0.82581 (12)	0.0152 (5)
C3	0.60829 (15)	0.4829 (5)	0.83024 (12)	0.0180 (5)
H3A	0.6381	0.5085	0.8778	0.022*
H3B	0.5899	0.2847	0.8259	0.022*
C4	0.72913 (14)	0.3572 (5)	0.74666 (12)	0.0144 (4)
C5	0.79056 (16)	0.4510 (5)	0.68634 (11)	0.0141 (5)
C6	0.87941 (15)	0.3419 (5)	0.68295 (12)	0.0144 (5)
H6	0.9001	0.2141	0.7186	0.017*
C7	0.93716 (15)	0.4205 (5)	0.62750 (12)	0.0148 (4)
C8	0.90958 (15)	0.6012 (5)	0.57315 (12)	0.0154 (5)
C9	0.81934 (15)	0.6983 (5)	0.57707 (12)	0.0148 (4)
C10	0.76008 (15)	0.6285 (4)	0.63220 (12)	0.0150 (4)
H10	0.6992	0.7008	0.6332	0.018*
H1	0.688 (2)	0.722 (3)	0.7627 (15)	0.034 (8)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0208 (2)	0.0329 (3)	0.0197 (3)	−0.0005 (2)	0.0067 (3)	0.0055 (3)
O1	0.0187 (8)	0.0221 (9)	0.0235 (9)	0.0055 (7)	0.0068 (7)	0.0057 (8)
O2	0.0229 (9)	0.0218 (9)	0.0250 (9)	0.0052 (7)	0.0007 (7)	0.0080 (8)
O3	0.0222 (8)	0.0118 (8)	0.0296 (9)	0.0021 (6)	0.0050 (8)	0.0042 (7)
O4	0.0222 (9)	0.0231 (10)	0.0381 (11)	0.0077 (7)	0.0013 (8)	0.0099 (9)
O5	0.0127 (8)	0.0264 (9)	0.0455 (11)	−0.0055 (7)	0.0033 (8)	0.0016 (9)
O6	0.0452 (10)	0.0165 (8)	0.0239 (9)	−0.0042 (8)	−0.0027 (9)	0.0078 (8)
O7	0.0313 (10)	0.0340 (11)	0.0334 (11)	−0.0022 (8)	−0.0180 (9)	0.0075 (9)
N1	0.0197 (9)	0.0095 (9)	0.0171 (9)	0.0005 (7)	0.0019 (8)	0.0020 (8)
N2	0.0140 (10)	0.0219 (11)	0.0206 (10)	−0.0005 (8)	−0.0006 (8)	0.0001 (9)
N3	0.0220 (9)	0.0187 (10)	0.0129 (9)	0.0047 (8)	0.0004 (8)	−0.0007 (8)
C1	0.0173 (11)	0.0303 (13)	0.0305 (13)	0.0060 (11)	0.0032 (11)	−0.0036 (13)
C2	0.0167 (10)	0.0155 (11)	0.0133 (11)	0.0003 (9)	−0.0011 (9)	−0.0038 (9)
C3	0.0195 (11)	0.0176 (12)	0.0171 (11)	0.0029 (9)	0.0023 (9)	0.0044 (9)
C4	0.0133 (9)	0.0149 (12)	0.0150 (10)	−0.0016 (8)	−0.0039 (9)	0.0012 (9)
C5	0.0152 (10)	0.0128 (11)	0.0142 (10)	−0.0023 (9)	−0.0013 (8)	−0.0019 (9)
C6	0.0158 (11)	0.0112 (11)	0.0161 (10)	0.0023 (9)	−0.0031 (9)	0.0005 (9)
C7	0.0111 (10)	0.0131 (10)	0.0201 (11)	0.0018 (9)	−0.0011 (9)	−0.0035 (9)
C8	0.0148 (10)	0.0163 (12)	0.0149 (10)	−0.0029 (9)	0.0026 (9)	−0.0019 (9)
C9	0.0186 (11)	0.0106 (11)	0.0151 (10)	0.0000 (9)	−0.0016 (9)	0.0011 (9)
C10	0.0154 (10)	0.0113 (10)	0.0185 (11)	0.0002 (9)	0.0001 (9)	−0.0029 (9)

Cl1—C8	1.718 (2)	C1—H1B	0.9800
O1—C2	1.333 (3)	C1—H1C	0.9800
O1—C1	1.453 (3)	C2—C3	1.507 (3)
O2—C2	1.198 (3)	C3—H3A	0.9900
O3—C4	1.235 (3)	C3—H3B	0.9900
O4—N2	1.228 (3)	C4—C5	1.499 (3)
O5—N2	1.218 (2)	C5—C10	1.388 (3)
O6—N3	1.218 (2)	C5—C6	1.394 (3)
O7—N3	1.213 (2)	C6—C7	1.379 (3)
N1—C4	1.331 (3)	C6—H6	0.9500
N1—C3	1.445 (3)	C7—C8	1.388 (3)
N1—H1	0.875 (10)	C8—C9	1.393 (3)
N2—C7	1.482 (3)	C9—C10	1.377 (3)
N3—C9	1.474 (3)	C10—H10	0.9500
C1—H1A	0.9800
C2—O1—C1	116.05 (18)	C2—C3—H3B	109.4
C4—N1—C3	121.01 (19)	H3A—C3—H3B	108.0
C4—N1—H1	115 (2)	O3—C4—N1	124.0 (2)
C3—N1—H1	123 (2)	O3—C4—C5	120.2 (2)
O5—N2—O4	124.78 (19)	N1—C4—C5	115.9 (2)
O5—N2—C7	118.92 (19)	C10—C5—C6	119.5 (2)
O4—N2—C7	116.30 (18)	C10—C5—C4	122.2 (2)
O7—N3—O6	125.1 (2)	C6—C5—C4	118.15 (19)
O7—N3—C9	116.80 (19)	C7—C6—C5	119.6 (2)
O6—N3—C9	118.10 (19)	C7—C6—H6	120.2
O1—C1—H1A	109.5	C5—C6—H6	120.2
O1—C1—H1B	109.5	C6—C7—C8	122.43 (19)
H1A—C1—H1B	109.5	C6—C7—N2	115.99 (19)
O1—C1—H1C	109.5	C8—C7—N2	121.56 (19)
H1A—C1—H1C	109.5	C7—C8—C9	116.3 (2)
H1B—C1—H1C	109.5	C7—C8—Cl1	123.59 (17)
O2—C2—O1	125.1 (2)	C9—C8—Cl1	119.92 (18)
O2—C2—C3	125.4 (2)	C10—C9—C8	123.1 (2)
O1—C2—C3	109.49 (19)	C10—C9—N3	117.46 (19)
N1—C3—C2	111.18 (18)	C8—C9—N3	119.4 (2)
N1—C3—H3A	109.4	C9—C10—C5	119.1 (2)
C2—C3—H3A	109.4	C9—C10—H10	120.5
N1—C3—H3B	109.4	C5—C10—H10	120.5
C1—O1—C2—O2	−1.9 (3)	O4—N2—C7—C8	−144.0 (2)
C1—O1—C2—C3	176.48 (19)	C6—C7—C8—C9	−0.6 (3)
C4—N1—C3—C2	−150.1 (2)	N2—C7—C8—C9	177.3 (2)
O2—C2—C3—N1	−7.6 (3)	C6—C7—C8—Cl1	−174.96 (18)
O1—C2—C3—N1	174.00 (19)	N2—C7—C8—Cl1	3.0 (3)
C3—N1—C4—O3	−2.2 (3)	C7—C8—C9—C10	1.7 (3)
C3—N1—C4—C5	177.61 (19)	Cl1—C8—C9—C10	176.32 (18)
O3—C4—C5—C10	139.5 (2)	C7—C8—C9—N3	−174.6 (2)
N1—C4—C5—C10	−40.3 (3)	Cl1—C8—C9—N3	−0.1 (3)
O3—C4—C5—C6	−36.8 (3)	O7—N3—C9—C10	−59.9 (3)
N1—C4—C5—C6	143.4 (2)	O6—N3—C9—C10	118.9 (2)
C10—C5—C6—C7	2.6 (3)	O7—N3—C9—C8	116.6 (2)
C4—C5—C6—C7	179.0 (2)	O6—N3—C9—C8	−64.5 (3)
C5—C6—C7—C8	−1.6 (3)	C8—C9—C10—C5	−0.7 (3)
C5—C6—C7—N2	−179.6 (2)	N3—C9—C10—C5	175.76 (19)
O5—N2—C7—C6	−144.8 (2)	C6—C5—C10—C9	−1.5 (3)
O4—N2—C7—C6	34.0 (3)	C4—C5—C10—C9	−177.75 (19)
O5—N2—C7—C8	37.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88 (1)	1.99 (1)	2.833 (3)	163 (3)
C1—H1a···O7ii	0.98	2.59	3.460 (3)	148
C3—H3a···O6iii	0.99	2.53	3.502 (3)	169
C3—H3b···O2iv	0.99	2.42	3.380 (3)	162
C10—H10···O5v	0.95	2.37	3.223 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88 (1)	1.99 (1)	2.833 (3)	163 (3)
C1—H1a⋯O7ii	0.98	2.59	3.460 (3)	148
C3—H3a⋯O6iii	0.99	2.53	3.502 (3)	169
C3—H3b⋯O2iv	0.99	2.42	3.380 (3)	162
C10—H10⋯O5v	0.95	2.37	3.223 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .