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

In the title picryl-substituted ester, C13H6BrN3O8, the mean plane of the central ester C-O-C(=O)-C fragment (r.m.s. deviation= 0.0186 Å) is rotated by 84.73 (7)° and 19.92 (12)° to the picryl and phenyl rings, respectively. In the crystal, the mol-ecules are linked by C-H⋯O inter-actions, forming centrosymmetric dimers enclosing R (2) 2(10) and R (2) 2(22) ring motifs along [001] and further helical chains of dimers enclosing R (2) 2(10) ring motifs along [010].

Related literature

For related structures, including isostructural 2,4,6-tri­nitro­phenyl 3-chloro­benzoate, see: Moreno-Fuquen et al. (2013a ▶,b ▶,c ▶). For a detailed study of the central ester moiety, see: Moreno-Fuquen et al. (2012 ▶). For hydrogen bonding, see: Nardelli (1995 ▶) and for hydrogen-bond graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C13H6BrN3O8

M = 412.12

Monoclinic,

a = 11.2925 (4) Å

b = 9.5672 (3) Å

c = 14.0560 (6) Å

β = 94.625 (2)°

V = 1513.63 (10) Å3

Z = 4

Mo Kα radiation

μ = 2.77 mm−1

T = 295 K

0.27 × 0.24 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.486, T max = 0.601

5971 measured reflections

3082 independent reflections

2572 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.03

3082 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.50 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814010952/fk2082sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010952/fk2082Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010952/fk2082Isup3.cml

CCDC reference: 1002544

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H6BrN3O8	F(000) = 816
Mr = 412.12	Dx = 1.808 Mg m−3
Monoclinic, P21/c	Melting point: 396(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.2925 (4) Å	Cell parameters from 5804 reflections
b = 9.5672 (3) Å	θ = 3.1–26.4°
c = 14.0560 (6) Å	µ = 2.77 mm−1
β = 94.625 (2)°	T = 295 K
V = 1513.63 (10) Å3	Block, pale-yellow
Z = 4	0.27 × 0.24 × 0.13 mm

Nonius KappaCCD diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	2572 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.486, Tmax = 0.601	k = −11→11
5971 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.7085P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3082 reflections	Δρmax = 0.42 e Å−3
227 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0122 (8)

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
Br1	0.42777 (2)	−0.02749 (3)	0.715747 (17)	0.05304 (13)
O1	0.1739 (2)	0.4619 (2)	0.36624 (13)	0.0651 (5)
O2	0.0830 (2)	0.5890 (2)	0.25761 (16)	0.0814 (7)
O3	−0.1211 (2)	0.3737 (3)	−0.01520 (17)	0.0930 (9)
O4	−0.06765 (18)	0.1728 (2)	−0.06105 (14)	0.0635 (5)
O5	0.3193 (2)	−0.0080 (2)	0.10541 (17)	0.0731 (6)
O6	0.2583 (2)	−0.0484 (2)	0.24323 (15)	0.0713 (6)
O7	0.28431 (12)	0.23650 (17)	0.30276 (10)	0.0385 (4)
O8	0.15437 (13)	0.14296 (19)	0.39805 (11)	0.0453 (4)
N1	0.12577 (19)	0.4786 (2)	0.28662 (15)	0.0457 (5)
N2	−0.06070 (18)	0.2704 (2)	−0.00614 (15)	0.0489 (5)
N3	0.26169 (17)	0.0199 (2)	0.17035 (15)	0.0445 (5)
C1	0.19417 (17)	0.2459 (2)	0.23105 (14)	0.0335 (5)
C2	0.11868 (19)	0.3606 (2)	0.21900 (15)	0.0360 (5)
C3	0.03478 (19)	0.3701 (2)	0.14191 (15)	0.0385 (5)
H3	−0.0167	0.4460	0.1351	0.046*
C4	0.02977 (18)	0.2642 (2)	0.07569 (14)	0.0356 (5)
C5	0.10472 (18)	0.1513 (2)	0.08195 (15)	0.0364 (5)
H5	0.1018	0.0829	0.0348	0.044*
C6	0.18467 (18)	0.1439 (2)	0.16128 (14)	0.0342 (5)
C7	0.25235 (18)	0.1838 (2)	0.38886 (14)	0.0355 (5)
C8	0.35354 (18)	0.1859 (2)	0.46246 (14)	0.0350 (5)
C9	0.4515 (2)	0.2719 (3)	0.45653 (16)	0.0435 (5)
H9	0.4574	0.3296	0.4039	0.052*
C10	0.5406 (2)	0.2703 (3)	0.53043 (18)	0.0531 (6)
H10	0.6060	0.3288	0.5276	0.064*
C11	0.5337 (2)	0.1834 (3)	0.60789 (17)	0.0482 (6)
H11	0.5939	0.1829	0.6571	0.058*
C12	0.43635 (19)	0.0970 (2)	0.61152 (15)	0.0383 (5)
C13	0.34547 (18)	0.0974 (2)	0.54011 (15)	0.0368 (5)
H13	0.2799	0.0394	0.5437	0.044*

	U11	U22	U33	U12	U13	U23
Br1	0.06119 (19)	0.0611 (2)	0.03652 (16)	0.01162 (12)	0.00239 (11)	0.01329 (11)
O1	0.0973 (15)	0.0632 (13)	0.0334 (10)	−0.0016 (11)	−0.0035 (9)	−0.0101 (9)
O2	0.1105 (18)	0.0569 (14)	0.0728 (14)	0.0343 (13)	−0.0170 (12)	−0.0218 (11)
O3	0.1003 (16)	0.0825 (16)	0.0870 (16)	0.0552 (14)	−0.0486 (13)	−0.0217 (13)
O4	0.0767 (12)	0.0491 (11)	0.0588 (12)	−0.0011 (10)	−0.0308 (10)	−0.0065 (9)
O5	0.0713 (13)	0.0773 (15)	0.0722 (15)	0.0310 (11)	0.0148 (11)	−0.0117 (11)
O6	0.0920 (15)	0.0594 (13)	0.0594 (13)	0.0284 (11)	−0.0131 (11)	0.0154 (10)
O7	0.0352 (7)	0.0526 (10)	0.0269 (7)	−0.0028 (7)	−0.0020 (6)	0.0040 (7)
O8	0.0388 (8)	0.0594 (11)	0.0369 (8)	−0.0083 (8)	−0.0021 (6)	0.0078 (8)
N1	0.0504 (11)	0.0471 (13)	0.0404 (11)	0.0032 (10)	0.0086 (9)	−0.0076 (9)
N2	0.0510 (12)	0.0476 (13)	0.0453 (11)	0.0063 (10)	−0.0137 (9)	0.0030 (10)
N3	0.0431 (11)	0.0434 (12)	0.0447 (12)	0.0097 (9)	−0.0103 (9)	−0.0057 (10)
C1	0.0333 (10)	0.0419 (12)	0.0249 (9)	−0.0002 (9)	0.0009 (8)	0.0042 (9)
C2	0.0408 (11)	0.0375 (12)	0.0302 (10)	0.0016 (10)	0.0052 (9)	−0.0017 (9)
C3	0.0404 (11)	0.0371 (12)	0.0379 (12)	0.0052 (10)	0.0034 (9)	0.0038 (10)
C4	0.0385 (11)	0.0381 (12)	0.0289 (10)	0.0024 (10)	−0.0044 (8)	0.0055 (9)
C5	0.0430 (11)	0.0369 (12)	0.0286 (10)	0.0014 (10)	−0.0009 (9)	0.0004 (9)
C6	0.0354 (10)	0.0360 (12)	0.0309 (10)	0.0057 (9)	0.0004 (8)	0.0040 (9)
C7	0.0394 (11)	0.0384 (12)	0.0283 (10)	0.0006 (10)	0.0000 (8)	0.0011 (9)
C8	0.0365 (10)	0.0388 (12)	0.0289 (10)	0.0022 (10)	−0.0013 (8)	−0.0013 (9)
C9	0.0451 (12)	0.0461 (14)	0.0382 (12)	−0.0038 (11)	−0.0030 (10)	0.0090 (10)
C10	0.0452 (13)	0.0570 (16)	0.0545 (15)	−0.0135 (12)	−0.0116 (11)	0.0084 (13)
C11	0.0445 (12)	0.0549 (15)	0.0423 (13)	0.0012 (12)	−0.0136 (10)	0.0027 (12)
C12	0.0445 (12)	0.0401 (13)	0.0300 (10)	0.0103 (10)	0.0008 (9)	0.0011 (9)
C13	0.0378 (11)	0.0392 (13)	0.0332 (11)	−0.0003 (10)	0.0016 (9)	−0.0002 (9)

Br1—C12	1.897 (2)	C3—C4	1.374 (3)
O1—N1	1.215 (3)	C3—H3	0.9300
O2—N1	1.218 (3)	C4—C5	1.370 (3)
O3—N2	1.201 (3)	C5—C6	1.379 (3)
O4—N2	1.210 (3)	C5—H5	0.9300
O5—N3	1.193 (3)	C7—C8	1.478 (3)
O6—N3	1.218 (3)	C8—C9	1.387 (3)
O7—C1	1.376 (2)	C8—C13	1.391 (3)
O7—C7	1.386 (2)	C9—C10	1.387 (3)
O8—C7	1.190 (2)	C9—H9	0.9300
N1—C2	1.474 (3)	C10—C11	1.377 (3)
N2—C4	1.477 (3)	C10—H10	0.9300
N3—C6	1.470 (3)	C11—C12	1.379 (3)
C1—C6	1.382 (3)	C11—H11	0.9300
C1—C2	1.392 (3)	C12—C13	1.376 (3)
C2—C3	1.384 (3)	C13—H13	0.9300
C1—O7—C7	115.73 (16)	C5—C6—C1	123.1 (2)
O1—N1—O2	123.9 (2)	C5—C6—N3	117.15 (19)
O1—N1—C2	119.4 (2)	C1—C6—N3	119.79 (18)
O2—N1—C2	116.7 (2)	O8—C7—O7	121.61 (18)
O3—N2—O4	124.0 (2)	O8—C7—C8	126.98 (19)
O3—N2—C4	117.8 (2)	O7—C7—C8	111.41 (17)
O4—N2—C4	118.1 (2)	C9—C8—C13	120.8 (2)
O5—N3—O6	125.4 (2)	C9—C8—C7	122.8 (2)
O5—N3—C6	118.0 (2)	C13—C8—C7	116.42 (19)
O6—N3—C6	116.5 (2)	C8—C9—C10	118.9 (2)
O7—C1—C6	118.96 (19)	C8—C9—H9	120.6
O7—C1—C2	123.38 (19)	C10—C9—H9	120.6
C6—C1—C2	117.32 (18)	C11—C10—C9	121.0 (2)
C3—C2—C1	121.4 (2)	C11—C10—H10	119.5
C3—C2—N1	116.9 (2)	C9—C10—H10	119.5
C1—C2—N1	121.65 (19)	C10—C11—C12	119.1 (2)
C4—C3—C2	118.0 (2)	C10—C11—H11	120.4
C4—C3—H3	121.0	C12—C11—H11	120.4
C2—C3—H3	121.0	C13—C12—C11	121.4 (2)
C5—C4—C3	123.1 (2)	C13—C12—Br1	118.90 (17)
C5—C4—N2	117.8 (2)	C11—C12—Br1	119.68 (16)
C3—C4—N2	119.1 (2)	C12—C13—C8	118.8 (2)
C4—C5—C6	117.0 (2)	C12—C13—H13	120.6
C4—C5—H5	121.5	C8—C13—H13	120.6
C6—C5—H5	121.5
C7—O7—C1—C6	−100.4 (2)	C2—C1—C6—C5	−0.1 (3)
C7—O7—C1—C2	86.5 (3)	O7—C1—C6—N3	6.8 (3)
O7—C1—C2—C3	175.27 (19)	C2—C1—C6—N3	−179.71 (19)
C6—C1—C2—C3	2.0 (3)	O5—N3—C6—C5	54.2 (3)
O7—C1—C2—N1	−3.6 (3)	O6—N3—C6—C5	−123.6 (2)
C6—C1—C2—N1	−176.81 (19)	O5—N3—C6—C1	−126.1 (2)
O1—N1—C2—C3	161.2 (2)	O6—N3—C6—C1	56.0 (3)
O2—N1—C2—C3	−19.6 (3)	C1—O7—C7—O8	3.6 (3)
O1—N1—C2—C1	−19.9 (3)	C1—O7—C7—C8	−176.60 (18)
O2—N1—C2—C1	159.3 (2)	O8—C7—C8—C9	−159.4 (2)
C1—C2—C3—C4	−1.6 (3)	O7—C7—C8—C9	20.8 (3)
N1—C2—C3—C4	177.32 (19)	O8—C7—C8—C13	19.8 (3)
C2—C3—C4—C5	−0.9 (3)	O7—C7—C8—C13	−159.95 (19)
C2—C3—C4—N2	178.70 (19)	C13—C8—C9—C10	−1.3 (4)
O3—N2—C4—C5	−175.1 (3)	C7—C8—C9—C10	177.9 (2)
O4—N2—C4—C5	3.3 (3)	C8—C9—C10—C11	1.1 (4)
O3—N2—C4—C3	5.3 (4)	C9—C10—C11—C12	−0.1 (4)
O4—N2—C4—C3	−176.3 (2)	C10—C11—C12—C13	−0.9 (4)
C3—C4—C5—C6	2.7 (3)	C10—C11—C12—Br1	178.1 (2)
N2—C4—C5—C6	−176.87 (19)	C11—C12—C13—C8	0.7 (3)
C4—C5—C6—C1	−2.2 (3)	Br1—C12—C13—C8	−178.21 (16)
C4—C5—C6—N3	177.4 (2)	C9—C8—C13—C12	0.4 (3)
O7—C1—C6—C5	−173.62 (19)	C7—C8—C13—C12	−178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.93	2.51	3.140 (3)	125
C11—H11···O6ii	0.93	2.46	3.282 (3)	148
C13—H13···O3iii	0.93	2.40	3.314 (3)	166
C3—H3···O8iv	0.93	2.46	3.391 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.93	2.51	3.140 (3)	125
C11—H11⋯O6ii	0.93	2.46	3.282 (3)	148
C13—H13⋯O3iii	0.93	2.40	3.314 (3)	166
C3—H3⋯O8iv	0.93	2.46	3.391 (3)	175

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