2,4,6-Tri-nitro-phenyl 3-chloro-benzoate.

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, mol-ecules are linked by weak C-H⋯O inter-actions, 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 = 367.66

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.162

S = 1.00

3383 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013792/hg5316sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013792/hg5316Isup3.cml

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

C13H6ClN3O8	F(000) = 744
Mr = 367.66	Dx = 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

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

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(Fo2) + (0.0973P)2] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O2iv	0.93	2.60	3.278 (3)	131
C5—H5···O8v	0.93	2.48	3.404 (3)	174

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⋯O2iv	0.93	2.60	3.278 (3)	131
C5—H5⋯O8v	0.93	2.48	3.404 (3)	174

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