2,4,6-Tri­nitro­phenyl 3-chloro­benzoate

Moreno-Fuquen, R.; Mosquera, F.; Ellena, J.; De Simone, C.A.; Tenorio, J.C.

doi:10.1107/S1600536813013792

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o966

doi:10.1107/S1600536813013792

Open

access

2,4,6-Trinitrophenyl 3-chlorobenzoate

Rodolfo Moreno-Fuquen,^a ^* Fabricio Mosquera,^a Javier Ellena,^b C. A. De Simone ^b and Juan C. Tenorio ^b

^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 16 May 2013; accepted 19 May 2013; online 25 May 2013)

In the title benzoate derivative, C₁₃H₆ClN₃O₈, the planes of the benzene rings form a dihedral angle of 73.59 (7)°. The central ester unit forms an angle of 20.38 (12)° with the chloro-substituted benzene ring. In the crystal, molecules are linked by weak C—H⋯O interactions, forming helical chains along [101] and [100].

Related literature

For investigations on reaction kinetics, see: Kirkien-Konasiewicz & Maccoll (1964 ); Belousova et al. (2000 ). For spectroscopic and theoretical studies, see: Ibrahim et al. (2011 ). For bond-length data, see: Allen et al. (1987 ). For similar structures, see: Moreno-Fuquen et al. (2012a ,b ,c , 2013 ). For hydrogen bonding, see: Nardelli (1995 ) and for hydrogen-bond motifs, see: Etter et al. (1990 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₃H₆ClN₃O₈
M_r = 367.66
Monoclinic, P 2₁ /c
a = 11.0633 (4) Å
b = 9.6560 (4) Å
c = 14.0251 (6) Å
β = 94.009 (2)°
V = 1494.60 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 295 K
0.24 × 0.24 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer
16939 measured reflections
3383 independent reflections
2015 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.162
S = 1.00
3383 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.93	2.50	3.167 (3)	128
C11—H11⋯O1ⁱⁱ	0.93	2.46	3.263 (3)	145
C13—H13⋯O4ⁱⁱⁱ	0.93	2.41	3.312 (3)	165
C10—H10⋯O2^iv	0.93	2.60	3.278 (3)	131
C5—H5⋯O8^v	0.93	2.48	3.404 (3)	174
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y, -z+1; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013792/hg5316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013792/hg5316Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013792/hg5316Isup3.cml

checkCIF report

Comment top

The title compound, C₁₃H₆ClN₃O₈[2,4,6-trinitrophenyl 3-chlorobenzoate] (I), belongs to a group of molecules known as picryl substituted-benzoates (or 2,4,6-trinitrofenil substituted-benzoates). Our research group has been lately investigating about this type of compound, in order to complete the crystallographic information around picryl substituted-benzoates. Also, the structural information can be linked or be useful to explain the results found at investigations of reaction kinetics (Kirkien-Konasiewicz & Maccoll, 1964; Belousova et al., 2000), spectroscopic behavior and theoretical studies (Ibrahim et al., 2011) underwent over this same group of compounds. The molecular structure of (I) is shown in Fig. 1, with a numbering scheme similar to that for TNP4ClBA (Moreno-Fuquen et al., 2013), 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. As a general fact, described deeply in previous papers (Moreno-Fuquen et al., 2012c and 2013), the structural parameters of substituted picryl benzoates, including (I), show significant differences in the bond distances C1—O7 and C7—O7 if they are compared with analogous distances in other phenyl benzoates reported in the literature (Allen, 2002, Version 5.33). The benzene rings of (I) form a dihedral angle of 73.59 (7)°. The central ester moiety forms an angle of 20.38 (12)° with the chloro-substituted benzene ring to which it is attached and an angle of 86.03 (7)° with the picryl ring. The nitro groups form dihedral angles with the adjacent benzene ring of 59.14 (9)°, 3.6 (2)° and 21.48 (14)° for O1—N1—O2, O3—N2—O4 and O5—N3—O6, respectively. The molecules are packed in a three dimensional network, through weak interactions C—H···O (see Table 1; Nardelli, 1995). Weak C3-H3···O3 and C11-H11···O1 contacts which reinforced each other, allow the molecules to propagate, forming one-dimensional helical chains, along [101]. Both weak contacts form dimers within the structure, as is shown in Fig. 2, and allow the formation of R₂²(10) and R₂²(22) rings respectively (Etter, 1990). In addition to the mentioned interactions other weak C-H···O interactions are observed. Indeed, the C13-H13···O4 and C10-H10···O2 weak contacts, form C(9) and C(12) chains of molecules allowing the crystal to grow also along [100] (see Fig. 3).

Related literature top

For investigations on reaction kinetics, see: Kirkien-Konasiewicz & Maccoll (1964); Belousova et al. (2000). For spectroscopic and theoretical studies, see: Ibrahim et al. (2011). For bond-length data, see: Allen et al. (1987). For similar structures, see: Moreno-Fuquen et al. (2012a,b,c, 2013). For hydrogen bonding, see: Nardelli (1995) and for hydrogen-bond motifs, see: Etter et al. (1990). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The 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. First the 3-chlorobenzoic acid (0.20g, 0.554 mmol) was refluxed in an excess of thionyl chloride (10 ml) during an hour. Then thionyl chloride was distilled off under reduced pressure to purify the 3-chorobenzoyl chloride obtained as a pale yellow traslucent liquid. The same reaction flask was rearranged and a solution of picric acid (0.12 g, 0.554 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 65%; m.p 408 (1)K. IR (KBr) 3092.32 cm^-1 (aromatic C—H); 1763.27 cm^-1 (ester C=O); 1615.65 cm^-1 (C=C); 1546.61 cm^-1, 1340.90 cm^-1 (–NO₂); 1216.82 cm^-1 (C(=O)—O).

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

	Fig. 1. Molecular conformation and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I), forming one-dimensional helical chains, along [101]. Symmetry code: (i) -x+2,-y,-z+2; (ii) -x+1,-y,-z+1.
	Fig. 3. Part of the crystal structure of (I), showing the formation of chains which running along along [100]. Symmetry code: (iii) -x+2,+y-1/2,-z+3/2; (iv) -x+1,+y+1/2,-z+3/2.

2,4,6-Trinitrophenyl 3-chlorobenzoate top

Crystal data top

C₁₃H₆ClN₃O₈	F(000) = 744
M_r = 367.66	D_x = 1.634 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 408(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.0633 (4) Å	Cell parameters from 6920 reflections
b = 9.6560 (4) Å	θ = 2.6–27.5°
c = 14.0251 (6) Å	µ = 0.31 mm⁻¹
β = 94.009 (2)°	T = 295 K
V = 1494.60 (10) Å³	Block, pale-yellow
Z = 4	0.24 × 0.24 × 0.17 mm

Data collection top

Nonius KappaCCD diffractometer	2015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
CCD rotation images, thick slices scans	h = −13→14
16939 measured reflections	k = −11→12
3383 independent reflections	l = −17→18

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0973P)²] where P = (F_o² + 2F_c²)/3
3383 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₃H₆ClN₃O₈	V = 1494.60 (10) Å³
M_r = 367.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0633 (4) Å	µ = 0.31 mm⁻¹
b = 9.6560 (4) Å	T = 295 K
c = 14.0251 (6) Å	0.24 × 0.24 × 0.17 mm
β = 94.009 (2)°

Data collection top

Nonius KappaCCD diffractometer	2015 reflections with I > 2σ(I)
16939 measured reflections	R_int = 0.069
3383 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
3383 reflections	Δρ_min = −0.27 e Å⁻³
227 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

	x	y	z	U_iso*/U_eq
Cl	0.56852 (7)	−0.00919 (7)	0.28977 (5)	0.0682 (3)
O7	0.71179 (13)	0.23513 (17)	0.69696 (10)	0.0502 (4)
O8	0.84485 (15)	0.14324 (18)	0.60062 (12)	0.0578 (5)
C13	0.6511 (2)	0.0995 (2)	0.45876 (16)	0.0471 (5)
H13	0.7174	0.0411	0.4550	0.057*
C3	0.8964 (2)	0.1510 (2)	0.91560 (16)	0.0465 (5)
H3	0.9003	0.0823	0.9622	0.056*
C1	0.80334 (19)	0.2457 (2)	0.76791 (15)	0.0440 (5)
N2	1.0634 (2)	0.2709 (2)	1.00374 (16)	0.0597 (6)
C8	0.6420 (2)	0.1866 (2)	0.53711 (16)	0.0464 (5)
C5	0.9641 (2)	0.3704 (2)	0.85707 (17)	0.0499 (6)
H5	1.0150	0.4469	0.8641	0.060*
N1	0.7383 (2)	0.0189 (2)	0.82752 (16)	0.0566 (5)
C7	0.7442 (2)	0.1841 (2)	0.61029 (16)	0.0474 (5)
C2	0.81502 (19)	0.1428 (2)	0.83739 (16)	0.0441 (5)
C6	0.8789 (2)	0.3605 (2)	0.78057 (16)	0.0470 (5)
O3	1.07187 (19)	0.17305 (19)	1.05824 (15)	0.0776 (6)
C12	0.5594 (2)	0.1017 (2)	0.38669 (16)	0.0503 (6)
O6	0.8224 (2)	0.4610 (2)	0.63360 (14)	0.0802 (6)
C4	0.9719 (2)	0.2641 (2)	0.92272 (16)	0.0469 (5)
N3	0.8689 (2)	0.4788 (2)	0.71367 (16)	0.0587 (6)
O1	0.7462 (2)	−0.0505 (2)	0.75600 (16)	0.0866 (7)
O5	0.9087 (2)	0.5889 (2)	0.74352 (17)	0.0942 (8)
C9	0.5427 (2)	0.2730 (3)	0.54277 (18)	0.0579 (6)
H9	0.5360	0.3292	0.5960	0.069*
O2	0.6754 (2)	−0.0070 (2)	0.89145 (18)	0.0891 (7)
O4	1.1242 (2)	0.3733 (2)	1.01268 (17)	0.1025 (8)
C11	0.4618 (2)	0.1893 (3)	0.3903 (2)	0.0652 (7)
H11	0.4016	0.1910	0.3406	0.078*
C10	0.4542 (3)	0.2748 (3)	0.4686 (2)	0.0697 (8)
H10	0.3884	0.3343	0.4713	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0769 (5)	0.0784 (5)	0.0485 (4)	−0.0108 (3)	−0.0009 (3)	−0.0157 (3)
O7	0.0480 (9)	0.0652 (10)	0.0368 (9)	0.0050 (7)	−0.0020 (7)	−0.0033 (7)
O8	0.0538 (10)	0.0734 (11)	0.0453 (10)	0.0105 (8)	−0.0036 (8)	−0.0074 (8)
C13	0.0495 (12)	0.0508 (13)	0.0408 (12)	0.0009 (10)	0.0008 (10)	0.0015 (10)
C3	0.0558 (13)	0.0431 (12)	0.0403 (12)	−0.0014 (10)	0.0003 (10)	0.0003 (9)
C1	0.0440 (12)	0.0551 (13)	0.0326 (11)	0.0029 (10)	0.0007 (9)	−0.0035 (9)
N2	0.0611 (13)	0.0580 (13)	0.0574 (14)	−0.0079 (10)	−0.0132 (10)	−0.0038 (10)
C8	0.0477 (13)	0.0512 (13)	0.0396 (12)	−0.0023 (10)	−0.0010 (10)	0.0024 (10)
C5	0.0533 (13)	0.0472 (12)	0.0491 (14)	−0.0072 (10)	0.0042 (11)	−0.0023 (10)
N1	0.0571 (12)	0.0555 (12)	0.0553 (13)	−0.0098 (9)	−0.0103 (10)	0.0040 (10)
C7	0.0533 (14)	0.0499 (13)	0.0385 (12)	0.0029 (10)	−0.0002 (10)	−0.0027 (10)
C2	0.0453 (12)	0.0461 (12)	0.0405 (12)	−0.0057 (9)	0.0004 (10)	−0.0036 (9)
C6	0.0522 (13)	0.0498 (13)	0.0393 (12)	−0.0007 (10)	0.0053 (10)	0.0013 (9)
O3	0.0935 (15)	0.0600 (12)	0.0733 (14)	−0.0002 (10)	−0.0353 (11)	0.0072 (10)
C12	0.0537 (14)	0.0548 (14)	0.0418 (13)	−0.0087 (10)	−0.0004 (10)	−0.0006 (10)
O6	0.1168 (18)	0.0773 (13)	0.0449 (11)	0.0013 (11)	−0.0049 (11)	0.0127 (9)
C4	0.0481 (12)	0.0509 (13)	0.0408 (12)	−0.0020 (10)	−0.0044 (10)	−0.0060 (10)
N3	0.0681 (14)	0.0589 (14)	0.0496 (13)	−0.0026 (10)	0.0087 (11)	0.0087 (10)
O1	0.1140 (18)	0.0723 (13)	0.0715 (15)	−0.0338 (12)	−0.0082 (13)	−0.0195 (11)
O5	0.130 (2)	0.0646 (13)	0.0845 (16)	−0.0310 (13)	−0.0140 (14)	0.0210 (12)
C9	0.0560 (14)	0.0650 (15)	0.0510 (15)	0.0085 (12)	−0.0076 (12)	−0.0121 (12)
O2	0.0872 (15)	0.0940 (16)	0.0878 (17)	−0.0358 (12)	0.0189 (13)	0.0113 (12)
O4	0.1119 (18)	0.0926 (16)	0.0960 (18)	−0.0533 (14)	−0.0425 (14)	0.0164 (13)
C11	0.0568 (15)	0.0773 (18)	0.0582 (17)	0.0004 (13)	−0.0189 (12)	−0.0063 (14)
C10	0.0617 (16)	0.0768 (18)	0.0680 (19)	0.0194 (14)	−0.0144 (14)	−0.0113 (15)

Geometric parameters (Å, º) top

Cl—C12	1.739 (2)	C8—C7	1.473 (3)
O7—C1	1.373 (3)	C5—C4	1.377 (3)
O7—C7	1.382 (3)	C5—C6	1.381 (3)
O8—C7	1.198 (3)	C5—H5	0.9300
C13—C12	1.382 (3)	N1—O2	1.199 (3)
C13—C8	1.393 (3)	N1—O1	1.215 (3)
C13—H13	0.9300	N1—C2	1.468 (3)
C3—C2	1.372 (3)	C6—N3	1.478 (3)
C3—C4	1.375 (3)	C12—C11	1.375 (3)
C3—H3	0.9300	O6—N3	1.214 (3)
C1—C2	1.392 (3)	N3—O5	1.213 (3)
C1—C6	1.392 (3)	C9—C10	1.379 (4)
N2—O4	1.198 (3)	C9—H9	0.9300
N2—O3	1.215 (3)	C11—C10	1.380 (4)
N2—C4	1.469 (3)	C11—H11	0.9300
C8—C9	1.386 (3)	C10—H10	0.9300

C1—O7—C7	116.14 (17)	C3—C2—C1	122.9 (2)
C12—C13—C8	118.5 (2)	C3—C2—N1	117.73 (19)
C12—C13—H13	120.7	C1—C2—N1	119.42 (19)
C8—C13—H13	120.7	C5—C6—C1	121.7 (2)
C2—C3—C4	117.7 (2)	C5—C6—N3	117.2 (2)
C2—C3—H3	121.1	C1—C6—N3	121.1 (2)
C4—C3—H3	121.1	C11—C12—C13	121.4 (2)
O7—C1—C2	118.82 (19)	C11—C12—Cl	119.78 (18)
O7—C1—C6	123.9 (2)	C13—C12—Cl	118.81 (19)
C2—C1—C6	117.0 (2)	C3—C4—C5	122.3 (2)
O4—N2—O3	123.9 (2)	C3—C4—N2	118.3 (2)
O4—N2—C4	118.0 (2)	C5—C4—N2	119.4 (2)
O3—N2—C4	118.1 (2)	O5—N3—O6	124.3 (2)
C9—C8—C13	120.7 (2)	O5—N3—C6	116.7 (2)
C9—C8—C7	122.8 (2)	O6—N3—C6	119.0 (2)
C13—C8—C7	116.5 (2)	C10—C9—C8	119.2 (2)
C4—C5—C6	118.4 (2)	C10—C9—H9	120.4
C4—C5—H5	120.8	C8—C9—H9	120.4
C6—C5—H5	120.8	C12—C11—C10	119.3 (2)
O2—N1—O1	125.6 (2)	C12—C11—H11	120.4
O2—N1—C2	117.5 (2)	C10—C11—H11	120.4
O1—N1—C2	116.9 (2)	C9—C10—C11	120.9 (2)
O8—C7—O7	121.1 (2)	C9—C10—H10	119.6
O8—C7—C8	126.9 (2)	C11—C10—H10	119.6
O7—C7—C8	111.96 (19)

C7—O7—C1—C2	−99.7 (2)	C2—C1—C6—C5	1.8 (3)
C7—O7—C1—C6	86.9 (3)	O7—C1—C6—N3	−3.1 (3)
C12—C13—C8—C9	0.3 (3)	C2—C1—C6—N3	−176.59 (19)
C12—C13—C8—C7	−177.8 (2)	C8—C13—C12—C11	1.2 (3)
C1—O7—C7—O8	4.8 (3)	C8—C13—C12—Cl	−178.73 (16)
C1—O7—C7—C8	−175.72 (18)	C2—C3—C4—C5	3.1 (3)
C9—C8—C7—O8	−158.6 (3)	C2—C3—C4—N2	−177.1 (2)
C13—C8—C7—O8	19.5 (4)	C6—C5—C4—C3	−1.4 (3)
C9—C8—C7—O7	21.9 (3)	C6—C5—C4—N2	178.8 (2)
C13—C8—C7—O7	−159.95 (19)	O4—N2—C4—C3	−175.8 (3)
C4—C3—C2—C1	−2.4 (3)	O3—N2—C4—C3	3.4 (3)
C4—C3—C2—N1	177.2 (2)	O4—N2—C4—C5	4.0 (4)
O7—C1—C2—C3	−173.9 (2)	O3—N2—C4—C5	−176.8 (2)
C6—C1—C2—C3	0.0 (3)	C5—C6—N3—O5	−20.4 (3)
O7—C1—C2—N1	6.5 (3)	C1—C6—N3—O5	158.0 (2)
C6—C1—C2—N1	−179.6 (2)	C5—C6—N3—O6	159.5 (2)
O2—N1—C2—C3	57.8 (3)	C1—C6—N3—O6	−22.1 (3)
O1—N1—C2—C3	−120.5 (2)	C13—C8—C9—C10	−1.8 (4)
O2—N1—C2—C1	−122.5 (3)	C7—C8—C9—C10	176.3 (2)
O1—N1—C2—C1	59.2 (3)	C13—C12—C11—C10	−1.3 (4)
C4—C5—C6—C1	−1.1 (3)	Cl—C12—C11—C10	178.6 (2)
C4—C5—C6—N3	177.3 (2)	C8—C9—C10—C11	1.6 (4)
O7—C1—C6—C5	175.3 (2)	C12—C11—C10—C9	−0.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.50	3.167 (3)	128
C11—H11···O1ⁱⁱ	0.93	2.46	3.263 (3)	145
C13—H13···O4ⁱⁱⁱ	0.93	2.41	3.312 (3)	165
C10—H10···O2^iv	0.93	2.60	3.278 (3)	131
C5—H5···O8^v	0.93	2.48	3.404 (3)	174

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₆ClN₃O₈
M_r	367.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.0633 (4), 9.6560 (4), 14.0251 (6)
β (°)	94.009 (2)
V (Å³)	1494.60 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.24 × 0.24 × 0.17

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16939, 3383, 2015
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.162, 1.00
No. of reflections	3383
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.27

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···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.50	3.167 (3)	128.4
C11—H11···O1ⁱⁱ	0.93	2.46	3.263 (3)	144.9
C13—H13···O4ⁱⁱⁱ	0.93	2.41	3.312 (3)	164.8
C10—H10···O2^iv	0.93	2.60	3.278 (3)	130.5
C5—H5···O8^v	0.93	2.48	3.404 (3)	174.3

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+2, y+1/2, −z+3/2.

Acknowledgements

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

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Belousova, I. A., Simanenko, Yu. S., Savelova, V. A. & Suprun, I. P. (2000). Russ. J. Org. Chem. 36, 1656–1664. CAS Google Scholar
Etter, M. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ibrahim, M. F., Senior, S. A., El-atawy, M. A., El-Sadany, S. K. & Hamed, E. A. (2011). J. Mol. Struct. 1006, 303–311. Web of Science CrossRef CAS Google Scholar
Kirkien-Konasiewicz, A. & Maccoll, A. (1964). J. Chem. Soc. pp. 1267–1274. Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Moreno-Fuquen, R., Mosquera, F., Ellena, J. & Tenorio, J. C. (2012a). Acta Cryst. E68, o2187. CSD CrossRef IUCr Journals Google Scholar
Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & Corrêa, R. S. (2012b). Acta Cryst. E68, o3107. CSD CrossRef IUCr Journals Google Scholar
Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & De Simone, C. A. (2013). Acta Cryst. E69, o570. CSD CrossRef IUCr Journals Google Scholar
Moreno-Fuquen, R., Mosquera, F., Kennedy, A. R., Morrison, C. A. & De Almeida Santos, R. H. (2012c). Acta Cryst. E68, o3493. CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
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. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar