organic compounds
(2-Chloro-3,5-dinitrophenyl)(piperidin-1-yl)methanone
aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
*Correspondence e-mail: yuluot@scu.edu.cn
In the title compound, C12H12ClN3O5, 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 intermolecular π–π stacking interactions 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
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Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell 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.
Supporting information
10.1107/S1600536811011469/bt5492sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811011469/bt5492Isup2.hkl
A solution of 3.42 g (12.9 mmol) of 2-chloro-3,5-dinitrobenzoyl chloride in 20 ml of dichloromethane was added to a solution of 1.097 g (12.9 mmol) piperidine with a catalyst of 1.82 g (17.9 mmol) triethylamine. The mixture was stirred for 2 h at room temperature and extracted with water and dichloromethane, then the organic solvent was evaporated and the title compound was recrystallized from ethanol (yield 3.24 g, 80%). Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of ethyl acetate.
Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell
CrysAlis PRO; data reduction: CrysAlis PRO (Oxford Diffraction, 2006); 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 (Dolomanov et al., 2009).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. A packing diagram of the title compound. |
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 monochromator | 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 |
C12H12ClN3O5 | V = 2637.60 (11) Å3 |
Mr = 313.70 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.7864 (3) Å | µ = 0.32 mm−1 |
b = 11.1264 (3) Å | T = 150 K |
c = 21.9775 (5) Å | 0.40 × 0.38 × 0.20 mm |
Oxford Diffraction Xcalibur Eos diffractometer | 2696 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) | 2240 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 1.0 | Rint = 0.021 |
6722 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.077 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.25 e Å−3 |
2696 reflections | Δρmin = −0.24 e Å−3 |
238 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | C12H12ClN3O5 |
Mr | 313.70 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 150 |
a, b, c (Å) | 10.7864 (3), 11.1264 (3), 21.9775 (5) |
V (Å3) | 2637.60 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.40 × 0.38 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.979, 1.0 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6722, 2696, 2240 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.077, 1.05 |
No. of reflections | 2696 |
No. of parameters | 238 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.25, −0.24 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.
References
Christophe, T., Jackson, M., Jeon, H. K., Fenistein, D., Contreras-Dominguez, M., Kim, J., Genovesio, A., Carralot, J. P., Ewann, F., Kim, E. H., Lee, S. Y., Kang, S., Seo, M. J., Park, E. J., Skovierova, H., Pham, H., Riccardi, G., Nam, J. Y., Marsollier, L., Kempf, M., Joly-Guillou, M. L., Oh, T., Shin, W. K., No, Z., Nehrbass, U., Brosch, R., Cole, S. T. & Brodin, P. (2009). PLoS Pathog. 5, 1–10. Web of Science CrossRef Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzamide derivatives are of great importance owing to their antibacterial properties (Christophe et al., 2009). The title compound is one of the key intermediates in our synthetic investigations of antibacterial drugs.
The piperidine ring adopts a chair conformation. As shown in Fig.1, the amide group forms a dihedral angles of 75.96 (5)° and 51.61 (9)° with the benzene ring and the piperidine ring, respectively. The crystal packing is strengthened by intermolecular π–π stacking interaction with centroid–centroid distances of 3.579 (3) Å.