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ISSN: 2056-9890

2,4,6-Tri­nitro­phenyl 4-chloro­benzoate

aDepartamento de Química – Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
*Correspondence e-mail: rodimo26@yahoo.es

(Received 25 February 2013; accepted 17 March 2013; online 23 March 2013)

In the title benzoate derivative, C13H6ClN3O8, the planes of the benzene rings form a dihedral angle of 63.46 (5)°. The dihedral angles between the benzene ring and its nitro groups are 12.78 (16)° for the first ortho, 28.4 (4) and 17.4 (4)° for the second (disordered) ortho and 3.58 (16)° for the para nitro group. The central ester moiety, –C—(C=O)—O–, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0229 Å) and forms dihedral angles of 7.37 (14)° with the chloro-substituted benzene ring and 69.85 (6)° with the trinitro-substituted benzene ring. One of the nitro groups was refined as disordered over two sets of sites with fixed site occupancies of 0.61 and 0.39. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the industrial and synthetic applications of nitroaryl compounds, see: Moreno-Fuquen et al. (2012a[Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012a). Acta Cryst. E68, o2187.]) and references therein. For similar structures, see: Moreno-Fuquen et al. (2012b[Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107.],c[Moreno-Fuquen, R., Mosquera, F., Kennedy, A. R., Morrison, C. A. & De Almeida Santos, R. H. (2012c). Acta Cryst. E68, o3493.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). For a description of the Cambridge Structural Database (CSD), see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C13H6ClN3O8

  • Mr = 367.66

  • Monoclinic, P 21 /c

  • a = 9.3526 (3) Å

  • b = 11.4793 (3) Å

  • c = 13.6089 (4) Å

  • β = 93.612 (2)°

  • V = 1458.17 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 295 K

  • 0.35 × 0.31 × 0.24 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 15908 measured reflections

  • 3288 independent reflections

  • 2424 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.151

  • S = 1.02

  • 3288 reflections

  • 246 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O4i 0.93 2.55 3.472 (3) 174
C5—H5⋯O8ii 0.93 2.53 3.457 (2) 174
C3—H3⋯O6Biii 0.93 2.36 3.188 (5) 147
C12—H12⋯O1iv 0.93 2.51 3.377 (2) 156
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+2.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

The title compound (I) belongs to a group of molecules known as nitro aryl benzoates. The vast applications at the industrial and synthetic level of nitro aryl compounds have been described in an earlier paper (Moreno-Fuquen et al., 2012a). Compound (I) is part of a series of studies on substituted 2,4,6-trinitrophenyl benzoates, also called picryl benzoates, undergone by our research group concerning the synthesis, properties and main features of the group of compounds. The molecular structure of (I) is shown in Fig. 1, with a numbering scheme similar to that for TNP3MeBA (Moreno-Fuquen et al., 2012a), TNP4MeBA (Moreno-Fuquen et al., 2012b) and TNPBA (Moreno-Fuquen et al., 2012c) in order to simplify structural comparisons. The substituted picryl benzoates, including (I), show noticeable differences only in C1—O7 and C7—O7 bond distances, if they are compared with bond and angles parameters in other phenyl benzoates reported in the Cambridge Structural Database (Version 5.33, Allen, 2002). This fact has been highlighted in previous papers (Moreno-Fuquen et al., 2012b,c) and it suggests a generalized effect over the ester moiety caused by the nitro substituents on the picryl fragment. The benzene rings of (I) form a dihedral angle of 63.46 (5)°. The central ester moiety forms an angle of 7.37 (14)° with the benzene ring to which it is attached. One of the nitro groups on the picryl fragment is disordered over two positions. The occupancies were initially refined but were fixed at 0.61 and 0.39 in the final cycles of refinement for O5A/O6A and O5B/O6B, respectively.

In the crystal, in a first substructure, the molecules are linked by weak C—H···O interactions, forming helical chains along [010]. The C5 atom of the phenyl ring at (x,y,z) acts as a hydrogen-bond donor to carbonyl atom O8 at (-x,+y + 1/2,-z + 3/2). Growth in this direction is reinforced by the weak C13—H13···O4 interaction, in which the C13 atom of the chloro substituted benzene ring at (x,y,z) acts as hydrogen-bond donor to atom O4 from one of the nitro groups at (-x, y-1/2, -z+3/2). The combination of these two contacts generate R22(10) rings (Etter et al., 1990), along [010] (See Fig. 2). This type of crystal growth for (I), was also observed for TNP3MeBA (Moreno-Fuquen et al., 2012a). Additionally to those interactions, other weak C—H···O contacts were observed in (I) and they complement the main growth previously described. In a second substructure shown in Fig. 3, it can be observed the formation of dimers through the weak C12—-H12···O1 interactions. Indeed, the C12 atom at (x,y,z) acts as hydrogen-bond donor to O1 atom of the nitro group at (-x+1,-y+1,-z+2) forming R22(20) rings (Etter et al., 1990). These dimers are clearly connected to each other, through the weak C3—H3···O6B contact, allowing them to grow along [001]. The C3 atom at (x,y,z) acts as a hydrogen-bond donor to O6B atom of the nitro group at (x,-y+3/2,+z-1/2). Hence, in the crystal, the formation of an overall three-dimensional structure is observed, via weak C—H···O hydrogen bonds (see Table 1, Nardelli, 1995).

Related literature top

For the industrial and synthetic applications of nitroaryl compounds, see: Moreno-Fuquen et al. (2012a) and references therein. For similar structures, see: Moreno-Fuquen et al. (2012b,c). For hydrogen bonding, see: Nardelli (1995). For hydrogen-bond motifs, see: Etter et al. (1990). For a description of the Cambridge Structural Database (CSD), see: Allen (2002).

Experimental top

Reagents and solvents for the synthesis were obtained from the Aldrich Chemical Co., and were used without additional purification. The title molecule was obtained through a two-step reaction model. First the 4-chlorobenzoic acid (0.270 g, 0.734 mmol) was refluxed in an excess amount of thionyl chloride (10 ml) during an hour. Then thionyl chloride was distilled under reduce pressure to purify the 4-chlorobenzoyl chloride obtained as a pale yellow traslucent liquid. The same reaction flask was rearranged and a solution of picric acid (0.170 g, 0.734 mmol) in acetonitrile, was added dropwise with constant stirring. The reaction mixture was left to reflux for about an hour. A pale yellow solid was obtained after leaving the solvent to evaporate. The solid was washed with distilled water and cold methanol to eliminate impurities. Crystals of good quality and suitable for single-crystal X-ray diffraction were grown from acetonitrile. IR spectra were recorded on a FT—IR SHIMADZU IR-Affinity-1 spectrophotometer. Pale Yellow crystals; yield 72%; m.p 433 (1) K. IR (KBr) 3096.55 cm-1 (aromatic C—H); 1752.53 cm-1 (ester C=O); 1615.98, 1590.04 cm-1 (C=C); 1543.34 cm-1, 1340.73 cm-1 (–NO2); 1218.96 cm-1 (C(=O)—O).

Refinement top

All H-atoms were positioned at geometrically idealized positions with C—H distance of 0.93 Å and Uiso(H) = 1.2 times Ueq of the C-atoms to which they were bonded.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius. The disorder of the O5/O6 atoms is shown.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing chains formed by weak C—H···O hydrogen bonds (dashed lines) which run along [010]. Symmetry code: (i) -x,+y + 1/2,-z + 3/2; (ii) -x, y+1/2, -z+3/2.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing chains formed by weak C—H···O hydrogen bonds (dashed lines) which run along [001]. Symmetry code: (iii) x,-y+3/2,+z-1/2; (iv) -x+1,-y+1,-z+2.
2,4,6-Trinitrophenyl 4-chlorobenzoate top
Crystal data top
C13H6ClN3O8F(000) = 744
Mr = 367.66Dx = 1.675 Mg m3
Monoclinic, P21/cMelting point: 433(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.3526 (3) ÅCell parameters from 7848 reflections
b = 11.4793 (3) Åθ = 2.6–27.5°
c = 13.6089 (4) ŵ = 0.32 mm1
β = 93.612 (2)°T = 295 K
V = 1458.17 (7) Å3Block, pale-yellow
Z = 40.35 × 0.31 × 0.24 mm
Data collection top
Nonius KappaCCD
diffractometer
2424 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
CCD rotation images, thick slices scansh = 1212
15908 measured reflectionsk = 1414
3288 independent reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.091P)2 + 0.2737P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3288 reflectionsΔρmax = 0.30 e Å3
246 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.045 (6)
Crystal data top
C13H6ClN3O8V = 1458.17 (7) Å3
Mr = 367.66Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3526 (3) ŵ = 0.32 mm1
b = 11.4793 (3) ÅT = 295 K
c = 13.6089 (4) Å0.35 × 0.31 × 0.24 mm
β = 93.612 (2)°
Data collection top
Nonius KappaCCD
diffractometer
2424 reflections with I > 2σ(I)
15908 measured reflectionsRint = 0.040
3288 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.02Δρmax = 0.30 e Å3
3288 reflectionsΔρmin = 0.24 e Å3
246 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.70639 (6)0.72855 (7)1.22374 (4)0.0773 (3)
N10.2976 (2)0.57696 (14)0.65153 (12)0.0561 (4)
N20.07414 (19)0.80404 (16)0.47344 (13)0.0582 (4)
N30.1244 (2)0.95193 (16)0.78955 (13)0.0630 (5)
O10.40062 (19)0.57284 (15)0.70877 (13)0.0772 (5)
O20.2690 (3)0.50235 (18)0.59209 (18)0.1161 (9)
O30.0786 (2)0.72668 (17)0.41290 (15)0.0935 (7)
O40.14293 (19)0.89346 (16)0.46545 (13)0.0783 (5)
O5A0.0210 (6)1.0035 (5)0.7997 (4)0.1039 (15)0.61
O6A0.2343 (8)0.9689 (6)0.8395 (6)0.169 (3)0.61
O5B0.0649 (8)1.0471 (5)0.7629 (5)0.0839 (18)0.39
O6B0.1736 (9)0.9336 (6)0.8683 (3)0.083 (2)0.39
O70.31371 (15)0.75992 (11)0.80241 (10)0.0511 (3)
O80.19504 (17)0.61439 (15)0.87062 (11)0.0698 (5)
C10.21381 (19)0.76369 (15)0.72449 (12)0.0427 (4)
C20.20321 (19)0.67959 (15)0.65074 (12)0.0438 (4)
C30.1074 (2)0.69124 (15)0.56973 (13)0.0469 (4)
H30.10000.63390.52140.056*
C40.0233 (2)0.78926 (15)0.56216 (13)0.0461 (4)
C50.0276 (2)0.87387 (16)0.63325 (13)0.0479 (4)
H50.03190.93870.62740.057*
C60.1229 (2)0.85976 (15)0.71372 (12)0.0455 (4)
C70.2931 (2)0.67990 (16)0.87591 (12)0.0457 (4)
C80.40200 (19)0.69270 (15)0.95775 (12)0.0435 (4)
C90.5009 (2)0.78335 (17)0.96322 (14)0.0522 (5)
H90.50370.83660.91190.063*
C100.5950 (2)0.79402 (19)1.04504 (15)0.0574 (5)
H100.66070.85491.04940.069*
C110.5907 (2)0.71382 (18)1.12019 (14)0.0528 (5)
C120.4945 (2)0.62241 (17)1.11557 (13)0.0513 (4)
H120.49360.56871.16670.062*
C130.3999 (2)0.61173 (16)1.03421 (12)0.0469 (4)
H130.33460.55051.03020.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0639 (4)0.1147 (6)0.0505 (3)0.0004 (3)0.0189 (2)0.0022 (3)
N10.0678 (11)0.0510 (9)0.0490 (9)0.0095 (7)0.0005 (8)0.0062 (7)
N20.0568 (10)0.0640 (10)0.0517 (9)0.0021 (8)0.0134 (7)0.0040 (8)
N30.0814 (13)0.0564 (10)0.0505 (10)0.0037 (9)0.0019 (9)0.0080 (8)
O10.0779 (11)0.0792 (11)0.0725 (11)0.0261 (9)0.0106 (9)0.0079 (8)
O20.150 (2)0.0794 (12)0.1119 (16)0.0508 (13)0.0479 (14)0.0421 (12)
O30.1134 (16)0.0845 (12)0.0754 (12)0.0096 (10)0.0499 (11)0.0188 (9)
O40.0763 (11)0.0838 (11)0.0717 (10)0.0233 (9)0.0195 (8)0.0077 (8)
O5A0.119 (4)0.093 (3)0.100 (4)0.039 (3)0.012 (2)0.036 (3)
O6A0.159 (6)0.114 (4)0.217 (8)0.052 (4)0.115 (5)0.106 (5)
O5B0.107 (5)0.066 (4)0.076 (4)0.025 (3)0.022 (3)0.022 (3)
O6B0.144 (6)0.080 (4)0.0251 (16)0.010 (3)0.008 (2)0.0062 (19)
O70.0551 (8)0.0567 (7)0.0399 (6)0.0104 (6)0.0098 (5)0.0117 (5)
O80.0708 (10)0.0877 (10)0.0489 (8)0.0328 (8)0.0119 (6)0.0194 (7)
C10.0458 (9)0.0473 (9)0.0344 (8)0.0055 (7)0.0011 (7)0.0073 (7)
C20.0508 (10)0.0414 (8)0.0390 (8)0.0001 (7)0.0005 (7)0.0060 (7)
C30.0569 (11)0.0440 (9)0.0394 (8)0.0039 (7)0.0013 (7)0.0003 (7)
C40.0469 (10)0.0506 (10)0.0398 (9)0.0033 (7)0.0052 (7)0.0049 (7)
C50.0492 (10)0.0487 (9)0.0456 (9)0.0030 (7)0.0019 (7)0.0045 (8)
C60.0532 (10)0.0454 (9)0.0379 (8)0.0015 (7)0.0037 (7)0.0008 (7)
C70.0515 (10)0.0521 (9)0.0333 (8)0.0019 (8)0.0018 (7)0.0028 (7)
C80.0462 (9)0.0497 (9)0.0344 (8)0.0027 (7)0.0012 (7)0.0005 (7)
C90.0554 (11)0.0614 (11)0.0391 (9)0.0068 (8)0.0027 (8)0.0059 (8)
C100.0570 (12)0.0676 (12)0.0465 (10)0.0103 (9)0.0055 (8)0.0004 (9)
C110.0468 (10)0.0723 (12)0.0384 (9)0.0095 (9)0.0044 (7)0.0026 (8)
C120.0543 (11)0.0598 (11)0.0396 (9)0.0112 (8)0.0005 (7)0.0073 (8)
C130.0510 (10)0.0497 (9)0.0399 (9)0.0038 (7)0.0019 (7)0.0026 (7)
Geometric parameters (Å, º) top
Cl1—C111.7301 (19)C2—C31.383 (2)
N1—O21.197 (2)C3—C41.373 (3)
N1—O11.201 (2)C3—H30.9300
N1—C21.472 (2)C4—C51.370 (3)
N2—O31.210 (2)C5—C61.377 (3)
N2—O41.213 (2)C5—H50.9300
N2—C41.476 (2)C7—C81.468 (2)
N3—O5A1.149 (5)C8—C91.391 (3)
N3—O6B1.159 (6)C8—C131.396 (2)
N3—O6A1.212 (6)C9—C101.380 (3)
N3—O5B1.269 (7)C9—H90.9300
N3—C61.477 (2)C10—C111.379 (3)
O7—C11.369 (2)C10—H100.9300
O7—C71.380 (2)C11—C121.381 (3)
O8—C71.185 (2)C12—C131.379 (3)
C1—C21.392 (2)C12—H120.9300
C1—C61.395 (3)C13—H130.9300
O2—N1—O1123.13 (18)C4—C5—C6117.85 (17)
O2—N1—C2117.33 (18)C4—C5—H5121.1
O1—N1—C2119.51 (17)C6—C5—H5121.1
O3—N2—O4124.39 (18)C5—C6—C1122.43 (16)
O3—N2—C4117.75 (17)C5—C6—N3116.64 (16)
O4—N2—C4117.86 (17)C1—C6—N3120.93 (17)
O5A—N3—O6B105.7 (5)O8—C7—O7121.40 (16)
O5A—N3—O6A122.7 (4)O8—C7—C8127.36 (16)
O6B—N3—O5B124.2 (5)O7—C7—C8111.19 (15)
O6A—N3—O5B111.3 (5)C9—C8—C13119.90 (17)
O5A—N3—C6118.8 (3)C9—C8—C7122.85 (16)
O6B—N3—C6120.1 (4)C13—C8—C7117.20 (16)
O6A—N3—C6118.5 (3)C10—C9—C8119.82 (18)
O5B—N3—C6115.6 (3)C10—C9—H9120.1
C1—O7—C7117.57 (14)C8—C9—H9120.1
O7—C1—C2123.42 (16)C11—C10—C9119.50 (19)
O7—C1—C6119.22 (16)C11—C10—H10120.2
C2—C1—C6117.23 (16)C9—C10—H10120.2
C3—C2—C1121.39 (16)C10—C11—C12121.54 (17)
C3—C2—N1116.22 (16)C10—C11—Cl1119.54 (16)
C1—C2—N1122.31 (16)C12—C11—Cl1118.91 (15)
C4—C3—C2118.59 (17)C13—C12—C11119.16 (17)
C4—C3—H3120.7C13—C12—H12120.4
C2—C3—H3120.7C11—C12—H12120.4
C5—C4—C3122.47 (17)C12—C13—C8120.06 (18)
C5—C4—N2119.06 (16)C12—C13—H13120.0
C3—C4—N2118.47 (16)C8—C13—H13120.0
C7—O7—C1—C274.2 (2)C2—C1—C6—N3178.57 (16)
C7—O7—C1—C6109.99 (18)O5A—N3—C6—C528.5 (4)
O7—C1—C2—C3175.31 (15)O6B—N3—C6—C5161.0 (5)
C6—C1—C2—C30.5 (2)O6A—N3—C6—C5152.5 (5)
O7—C1—C2—N11.4 (3)O5B—N3—C6—C516.5 (5)
C6—C1—C2—N1177.23 (15)O5A—N3—C6—C1151.2 (4)
O2—N1—C2—C312.3 (3)O6B—N3—C6—C118.8 (5)
O1—N1—C2—C3165.66 (18)O6A—N3—C6—C127.7 (6)
O2—N1—C2—C1170.8 (2)O5B—N3—C6—C1163.7 (4)
O1—N1—C2—C111.2 (3)C1—O7—C7—O82.2 (3)
C1—C2—C3—C41.1 (3)C1—O7—C7—C8175.40 (14)
N1—C2—C3—C4175.83 (16)O8—C7—C8—C9170.4 (2)
C2—C3—C4—C52.1 (3)O7—C7—C8—C96.9 (3)
C2—C3—C4—N2177.22 (16)O8—C7—C8—C137.0 (3)
O3—N2—C4—C5178.2 (2)O7—C7—C8—C13175.63 (15)
O4—N2—C4—C52.8 (3)C13—C8—C9—C101.1 (3)
O3—N2—C4—C32.4 (3)C7—C8—C9—C10176.21 (17)
O4—N2—C4—C3176.62 (19)C8—C9—C10—C110.6 (3)
C3—C4—C5—C61.5 (3)C9—C10—C11—C120.2 (3)
N2—C4—C5—C6177.86 (16)C9—C10—C11—Cl1178.89 (16)
C4—C5—C6—C10.2 (3)C10—C11—C12—C130.5 (3)
C4—C5—C6—N3179.55 (17)Cl1—C11—C12—C13178.57 (14)
O7—C1—C6—C5174.83 (15)C11—C12—C13—C80.0 (3)
C2—C1—C6—C51.2 (3)C9—C8—C13—C120.8 (3)
O7—C1—C6—N35.4 (2)C7—C8—C13—C12176.69 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O4i0.932.553.472 (3)174
C5—H5···O8ii0.932.533.457 (2)174
C3—H3···O6Biii0.932.363.188 (5)147
C12—H12···O1iv0.932.513.377 (2)156
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1/2, z+3/2; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC13H6ClN3O8
Mr367.66
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)9.3526 (3), 11.4793 (3), 13.6089 (4)
β (°) 93.612 (2)
V3)1458.17 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.35 × 0.31 × 0.24
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15908, 3288, 2424
Rint0.040
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.151, 1.02
No. of reflections3288
No. of parameters246
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.24

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O4i0.932.553.472 (3)173.8
C5—H5···O8ii0.932.533.457 (2)174.4
C3—H3···O6Biii0.932.363.188 (5)147.4
C12—H12···O1iv0.932.513.377 (2)156.0
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1/2, z+3/2; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z+2.
 

Acknowledgements

RMF is grateful to the Universidad del Valle, Colombia, for partial financial support.

References

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