(2-Chloro-3,5-dinitro-phen-yl)(piperidin-1-yl)methanone.

In the title compound, C(12)H(12)ClN(3)O(5), the piperidine ring adopts a chair conformation. One of the nitro groups is almost coplanar with the aromatic ring [O-N-C-C = -1.4 (2)°], whereas the other one is significantly twisted out of the ring plane [O-N-C-C = 34.7 (2)°]. The crystal packing is stabilized by inter-molecular π-π stacking inter-actions with centroid-centroid distances of 3.579 (3) Å.

Related literature

For the biological activity of benzamide derivatives, see: Christophe et al. (2009 ▶).

Experimental

Crystal data

C12H12ClN3O5

M = 313.70

Orthorhombic,

a = 10.7864 (3) Å

b = 11.1264 (3) Å

c = 21.9775 (5) Å

V = 2637.60 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 150 K

0.40 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.979, T max = 1.0

6722 measured reflections

2696 independent reflections

2240 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.077

S = 1.05

2696 reflections

238 parameters

All H-atom parameters refined

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011469/bt5492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011469/bt5492Isup2.hkl

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

C12H12ClN3O5	F(000) = 1296
Mr = 313.70	Dx = 1.580 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3316 reflections
a = 10.7864 (3) Å	θ = 3.2–29.1°
b = 11.1264 (3) Å	µ = 0.32 mm−1
c = 21.9775 (5) Å	T = 150 K
V = 2637.60 (11) Å3	Block, yellow
Z = 8	0.40 × 0.38 × 0.20 mm

Oxford Diffraction Xcalibur Eos diffractometer	2696 independent reflections
Radiation source: fine-focus sealed tube	2240 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −13→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −13→13
Tmin = 0.979, Tmax = 1.0	l = −27→15
6722 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.9862P] where P = (Fo2 + 2Fc2)/3
2696 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.24 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
Cl1	0.14710 (4)	0.51437 (4)	0.126198 (18)	0.02618 (12)
O1	0.28382 (11)	0.39665 (10)	0.03083 (6)	0.0308 (3)
O2	0.37259 (10)	0.52238 (11)	−0.03080 (6)	0.0297 (3)
O3	0.06436 (13)	0.74355 (12)	−0.14870 (6)	0.0376 (3)
O4	−0.09872 (13)	0.81129 (12)	−0.10265 (6)	0.0409 (4)
O5	−0.18116 (11)	0.60708 (11)	0.10878 (6)	0.0331 (3)
N1	0.28706 (12)	0.49108 (12)	0.00224 (6)	0.0219 (3)
N2	−0.00012 (14)	0.75653 (13)	−0.10356 (7)	0.0269 (3)
N3	−0.05433 (13)	0.73621 (12)	0.15851 (6)	0.0238 (3)
C1	0.10865 (14)	0.58412 (14)	0.05898 (7)	0.0179 (3)
C2	0.17880 (14)	0.57192 (13)	0.00600 (7)	0.0178 (3)
C3	0.14762 (15)	0.63140 (14)	−0.04708 (7)	0.0188 (3)
H3	0.1955 (17)	0.6182 (15)	−0.0830 (8)	0.028 (5)*
C4	0.04113 (15)	0.69969 (13)	−0.04645 (7)	0.0191 (3)
C5	−0.03125 (16)	0.71333 (14)	0.00470 (7)	0.0204 (4)
H5	−0.1055 (16)	0.7566 (15)	0.0036 (7)	0.018 (4)*
C6	0.00352 (14)	0.65690 (13)	0.05846 (7)	0.0177 (3)
C7	−0.08451 (15)	0.66492 (14)	0.11200 (7)	0.0207 (3)
C8	0.05941 (16)	0.80784 (16)	0.16249 (9)	0.0274 (4)
H8A	0.1068 (18)	0.7963 (17)	0.1263 (9)	0.034 (5)*
H8B	0.1111 (17)	0.7754 (16)	0.1984 (9)	0.032 (5)*
C9	0.02738 (18)	0.93938 (16)	0.17196 (8)	0.0274 (4)
H9A	−0.0143 (18)	0.9693 (16)	0.1353 (9)	0.031 (5)*
H9B	0.1038 (18)	0.9841 (16)	0.1769 (8)	0.029 (5)*
C10	−0.05450 (17)	0.95620 (17)	0.22745 (8)	0.0274 (4)
H10A	−0.0069 (16)	0.9325 (15)	0.2639 (8)	0.025 (5)*
H10B	−0.0785 (17)	1.0388 (17)	0.2320 (8)	0.033 (5)*
C11	−0.16990 (17)	0.87786 (17)	0.22253 (9)	0.0306 (4)
H11A	−0.2230 (19)	0.9067 (18)	0.1888 (9)	0.040 (6)*
H11B	−0.2193 (18)	0.8836 (16)	0.2593 (10)	0.041 (6)*
C12	−0.13634 (17)	0.74677 (16)	0.21155 (8)	0.0269 (4)
H12A	−0.2103 (16)	0.7001 (15)	0.2041 (8)	0.022 (4)*
H12B	−0.0908 (17)	0.7123 (15)	0.2473 (9)	0.028 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0277 (2)	0.0334 (2)	0.0174 (2)	0.00122 (18)	−0.00259 (17)	0.00550 (16)
O1	0.0322 (7)	0.0251 (6)	0.0350 (7)	0.0091 (6)	−0.0015 (6)	0.0029 (6)
O2	0.0189 (6)	0.0370 (7)	0.0332 (7)	−0.0013 (5)	0.0053 (5)	−0.0070 (6)
O3	0.0446 (8)	0.0466 (8)	0.0216 (7)	−0.0021 (7)	−0.0007 (6)	0.0093 (6)
O4	0.0399 (8)	0.0395 (8)	0.0434 (8)	0.0123 (7)	−0.0068 (7)	0.0168 (7)
O5	0.0250 (6)	0.0402 (7)	0.0341 (7)	−0.0139 (6)	0.0082 (6)	−0.0182 (6)
N1	0.0188 (7)	0.0246 (7)	0.0222 (7)	0.0011 (6)	−0.0029 (6)	−0.0045 (6)
N2	0.0329 (8)	0.0232 (7)	0.0246 (8)	−0.0050 (7)	−0.0055 (7)	0.0064 (6)
N3	0.0220 (7)	0.0285 (7)	0.0209 (7)	−0.0096 (6)	0.0061 (6)	−0.0079 (6)
C1	0.0199 (7)	0.0175 (8)	0.0162 (7)	−0.0048 (7)	−0.0022 (7)	0.0008 (6)
C2	0.0172 (7)	0.0166 (8)	0.0198 (8)	−0.0012 (7)	−0.0015 (6)	−0.0035 (6)
C3	0.0215 (8)	0.0191 (8)	0.0159 (8)	−0.0049 (7)	0.0011 (7)	−0.0026 (6)
C4	0.0244 (8)	0.0141 (7)	0.0187 (8)	−0.0030 (7)	−0.0036 (7)	0.0014 (6)
C5	0.0203 (8)	0.0154 (8)	0.0256 (9)	0.0010 (7)	−0.0010 (7)	−0.0022 (7)
C6	0.0193 (7)	0.0151 (7)	0.0186 (8)	−0.0038 (6)	0.0001 (7)	−0.0048 (6)
C7	0.0205 (8)	0.0189 (8)	0.0228 (9)	−0.0007 (7)	0.0018 (7)	−0.0032 (7)
C8	0.0225 (9)	0.0332 (10)	0.0266 (10)	−0.0106 (8)	0.0062 (8)	−0.0110 (8)
C9	0.0303 (10)	0.0295 (10)	0.0224 (9)	−0.0119 (8)	0.0016 (8)	−0.0023 (7)
C10	0.0308 (9)	0.0256 (9)	0.0258 (9)	−0.0027 (8)	0.0018 (8)	−0.0077 (8)
C11	0.0261 (9)	0.0381 (11)	0.0277 (10)	−0.0018 (8)	0.0076 (8)	−0.0098 (8)
C12	0.0272 (9)	0.0322 (9)	0.0212 (9)	−0.0100 (8)	0.0084 (8)	−0.0058 (8)

Cl1—C1	1.7196 (16)	C5—H5	0.935 (17)
O1—N1	1.2247 (17)	C5—C6	1.389 (2)
O2—N1	1.2246 (17)	C6—C7	1.515 (2)
O3—N2	1.2200 (19)	C8—H8A	0.95 (2)
O4—N2	1.2260 (19)	C8—H8B	1.032 (19)
O5—C7	1.2273 (19)	C8—C9	1.518 (3)
N1—C2	1.476 (2)	C9—H9A	0.98 (2)
N2—C4	1.474 (2)	C9—H9B	0.97 (2)
N3—C7	1.334 (2)	C9—C10	1.517 (2)
N3—C8	1.466 (2)	C10—H10A	0.987 (18)
N3—C12	1.468 (2)	C10—H10B	0.960 (19)
C1—C2	1.395 (2)	C10—C11	1.523 (2)
C1—C6	1.394 (2)	C11—H11A	0.99 (2)
C2—C3	1.383 (2)	C11—H11B	0.97 (2)
C3—H3	0.954 (18)	C11—C12	1.522 (3)
C3—C4	1.377 (2)	C12—H12A	0.966 (17)
C4—C5	1.377 (2)	C12—H12B	1.004 (19)
O1—N1—C2	118.12 (13)	C6—C1—Cl1	117.75 (12)
O2—N1—O1	124.73 (14)	C6—C1—C2	119.41 (14)
O2—N1—C2	117.11 (13)	C6—C5—H5	119.0 (10)
O3—N2—O4	124.53 (15)	C7—N3—C8	124.97 (14)
O3—N2—C4	118.00 (14)	C7—N3—C12	120.59 (13)
O4—N2—C4	117.45 (15)	C8—N3—C12	114.43 (13)
O5—C7—N3	124.28 (15)	C8—C9—H9A	108.6 (11)
O5—C7—C6	117.18 (14)	C8—C9—H9B	108.5 (10)
N3—C7—C6	118.51 (13)	H8A—C8—H8B	107.6 (15)
N3—C8—H8A	109.0 (11)	C9—C8—H8A	111.5 (12)
N3—C8—H8B	107.9 (10)	C9—C8—H8B	110.8 (10)
N3—C8—C9	109.99 (15)	C9—C10—H10A	108.5 (10)
N3—C12—C11	110.24 (15)	C9—C10—H10B	111.1 (11)
N3—C12—H12A	108.7 (10)	C9—C10—C11	110.37 (15)
N3—C12—H12B	107.2 (10)	H9A—C9—H9B	107.9 (15)
C1—C2—N1	122.34 (14)	C10—C9—C8	111.20 (15)
C1—C6—C7	122.55 (14)	C10—C9—H9A	110.6 (11)
C2—C1—Cl1	122.84 (12)	C10—C9—H9B	110.0 (11)
C2—C3—H3	119.5 (11)	C10—C11—H11A	109.9 (12)
C3—C2—N1	115.90 (14)	C10—C11—H11B	110.6 (11)
C3—C2—C1	121.70 (14)	H10A—C10—H10B	108.1 (15)
C3—C4—N2	118.68 (14)	C11—C10—H10A	109.2 (10)
C4—C3—C2	117.30 (15)	C11—C10—H10B	109.5 (11)
C4—C3—H3	122.9 (11)	C11—C12—H12A	110.2 (10)
C4—C5—H5	121.5 (10)	C11—C12—H12B	111.0 (10)
C4—C5—C6	119.43 (15)	H11A—C11—H11B	106.6 (16)
C5—C4—N2	118.47 (14)	C12—C11—C10	111.42 (15)
C5—C4—C3	122.80 (15)	C12—C11—H11A	109.2 (12)
C5—C6—C1	119.29 (14)	C12—C11—H11B	109.0 (11)
C5—C6—C7	117.69 (14)	H12A—C12—H12B	109.3 (14)
Cl1—C1—C2—N1	4.4 (2)	C2—C3—C4—N2	−175.24 (14)
Cl1—C1—C2—C3	−178.34 (12)	C2—C3—C4—C5	2.1 (2)
Cl1—C1—C6—C5	−179.12 (12)	C3—C4—C5—C6	0.3 (2)
Cl1—C1—C6—C7	−7.17 (19)	C4—C5—C6—C1	−2.2 (2)
O1—N1—C2—C1	34.7 (2)	C4—C5—C6—C7	−174.59 (14)
O1—N1—C2—C3	−142.65 (15)	C5—C6—C7—O5	71.21 (19)
O2—N1—C2—C1	−147.16 (15)	C5—C6—C7—N3	−106.95 (18)
O2—N1—C2—C3	35.45 (19)	C6—C1—C2—N1	−176.46 (13)
O3—N2—C4—C3	−2.2 (2)	C6—C1—C2—C3	0.8 (2)
O3—N2—C4—C5	−179.72 (14)	C7—N3—C8—C9	123.65 (18)
O4—N2—C4—C3	176.04 (14)	C7—N3—C12—C11	−124.47 (17)
O4—N2—C4—C5	−1.4 (2)	C8—N3—C7—O5	−178.63 (17)
N1—C2—C3—C4	174.76 (13)	C8—N3—C7—C6	−0.6 (2)
N2—C4—C5—C6	177.67 (14)	C8—N3—C12—C11	56.3 (2)
N3—C8—C9—C10	55.5 (2)	C8—C9—C10—C11	−55.0 (2)
C1—C2—C3—C4	−2.6 (2)	C9—C10—C11—C12	54.1 (2)
C1—C6—C7—O5	−100.86 (19)	C10—C11—C12—N3	−53.7 (2)
C1—C6—C7—N3	81.0 (2)	C12—N3—C7—O5	2.2 (3)
C2—C1—C6—C5	1.7 (2)	C12—N3—C7—C6	−179.80 (15)
C2—C1—C6—C7	173.67 (14)	C12—N3—C8—C9	−57.1 (2)