6,6'-Di-nitro-1,1'-(ethane-1,2-di-yl)di(1H-indazole).

The mol-ecule of the title compound, C16H12N6O4, is built up from two fused five- and six-membered rings linked by an ethyl-ene group. The dihedral angle between the planes through the indazole ring systems is 39.74 (5)°. The nitro groups are tilted by 7.2 (2) and 8.5 (2)° with respect to planes of the fused-ring systems. In the crystal, mol-ecules are linked by C-H⋯N and C-H⋯O hydrogen bonds into chains running parallel to the c axis.

Related literature

For biological activities of the indazole moiety, see: Ali et al. (2012 ▶); Abbassi et al. (2012 ▶); Plescia et al. (2010 ▶); Lee et al. (2001 ▶); Liu et al. (2011 ▶). For related compounds, see: Kouakou et al. (2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C16H12N6O4

M = 352.32

Monoclinic,

a = 9.410 (5) Å

b = 12.064 (5) Å

c = 14.804 (4) Å

β = 109.01 (2)°

V = 1588.9 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.37 × 0.32 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer

16446 measured reflections

3503 independent reflections

2667 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.03

3503 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814004516/rz5107sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004516/rz5107Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004516/rz5107Isup3.cml

CCDC reference: 988920

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

C16H12N6O4	F(000) = 728
Mr = 352.32	Dx = 1.473 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3672 reflections
a = 9.410 (5) Å	θ = 1.5–27.1°
b = 12.064 (5) Å	µ = 0.11 mm−1
c = 14.804 (4) Å	T = 296 K
β = 109.01 (2)°	Block, colourless
V = 1588.9 (12) Å3	0.37 × 0.32 × 0.26 mm
Z = 4

Bruker X8 APEX diffractometer	2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.1°, θmin = 2.8°
φ and ω scans	h = −12→12
16446 measured reflections	k = −15→15
3503 independent reflections	l = −18→18

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.3594P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3503 reflections	Δρmax = 0.20 e Å−3
236 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (10)

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
O1	0.72668 (16)	0.44512 (14)	0.20575 (10)	0.0753 (4)
O2	0.8642 (2)	0.57503 (14)	0.28985 (14)	0.1037 (6)
O3	1.06798 (18)	0.14604 (14)	0.75890 (9)	0.0817 (5)
O4	1.28535 (16)	0.17800 (15)	0.74730 (11)	0.0990 (6)
N1	0.78171 (17)	0.49484 (13)	0.28105 (13)	0.0617 (4)
N2	0.53003 (16)	0.25102 (14)	0.54188 (9)	0.0580 (4)
N3	0.54014 (13)	0.24766 (11)	0.45233 (8)	0.0435 (3)
N4	0.74940 (12)	0.09097 (10)	0.40649 (8)	0.0384 (3)
N5	0.74567 (15)	0.09998 (12)	0.31430 (8)	0.0487 (3)
N6	1.15060 (18)	0.16124 (12)	0.71175 (11)	0.0612 (4)
C1	0.74301 (17)	0.45822 (13)	0.36515 (12)	0.0474 (4)
C2	0.7928 (2)	0.52228 (15)	0.44873 (15)	0.0630 (5)
H2	0.8535	0.5839	0.4515	0.076*
C3	0.7517 (2)	0.49382 (17)	0.52569 (14)	0.0669 (5)
H3	0.7817	0.5367	0.5809	0.080*
C4	0.66362 (18)	0.39900 (15)	0.52037 (11)	0.0504 (4)
C5	0.62089 (15)	0.33505 (12)	0.43641 (10)	0.0386 (3)
C6	0.65760 (16)	0.36455 (12)	0.35590 (10)	0.0407 (3)
H6	0.6263	0.3234	0.2997	0.049*
C7	0.6008 (2)	0.34107 (18)	0.58152 (12)	0.0645 (5)
H7	0.6090	0.3644	0.6429	0.077*
C8	0.49431 (15)	0.14827 (13)	0.39587 (11)	0.0439 (4)
H8A	0.4747	0.1659	0.3290	0.053*
H8B	0.4017	0.1208	0.4030	0.053*
C9	0.61375 (15)	0.05839 (13)	0.42568 (11)	0.0443 (4)
H9A	0.6375	0.0436	0.4934	0.053*
H9B	0.5748	−0.0094	0.3912	0.053*
C10	0.87881 (19)	0.13663 (14)	0.31726 (11)	0.0505 (4)
H10	0.9067	0.1501	0.2635	0.061*
C11	0.97408 (16)	0.15298 (12)	0.41201 (10)	0.0401 (3)
C12	1.12332 (17)	0.18656 (13)	0.45625 (13)	0.0511 (4)
H12	1.1830	0.2074	0.4199	0.061*
C13	1.17921 (16)	0.18815 (13)	0.55331 (13)	0.0520 (4)
H13	1.2785	0.2087	0.5841	0.062*
C14	1.08659 (16)	0.15870 (12)	0.60685 (11)	0.0433 (4)
C15	0.93939 (15)	0.12611 (12)	0.56797 (10)	0.0375 (3)
H15	0.8802	0.1076	0.6052	0.045*
C16	0.88544 (14)	0.12277 (11)	0.46851 (9)	0.0337 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0816 (9)	0.0892 (11)	0.0650 (9)	0.0071 (8)	0.0377 (7)	0.0152 (8)
O2	0.1124 (13)	0.0726 (11)	0.1501 (16)	−0.0232 (10)	0.0756 (12)	0.0175 (10)
O3	0.0884 (10)	0.1023 (12)	0.0437 (7)	0.0028 (9)	0.0066 (7)	−0.0094 (7)
O4	0.0647 (9)	0.1077 (13)	0.0874 (11)	−0.0184 (8)	−0.0262 (8)	−0.0118 (9)
N1	0.0585 (9)	0.0505 (9)	0.0863 (12)	0.0087 (7)	0.0376 (8)	0.0203 (8)
N2	0.0521 (8)	0.0823 (11)	0.0423 (8)	0.0015 (8)	0.0193 (6)	0.0077 (7)
N3	0.0397 (6)	0.0518 (8)	0.0396 (7)	−0.0015 (6)	0.0139 (5)	0.0034 (5)
N4	0.0345 (6)	0.0445 (7)	0.0350 (6)	−0.0009 (5)	0.0096 (5)	0.0047 (5)
N5	0.0539 (8)	0.0556 (8)	0.0348 (7)	0.0022 (6)	0.0122 (5)	0.0045 (6)
N6	0.0602 (9)	0.0482 (9)	0.0565 (9)	−0.0003 (7)	−0.0065 (7)	−0.0092 (7)
C1	0.0448 (8)	0.0398 (9)	0.0594 (10)	0.0049 (7)	0.0195 (7)	0.0067 (7)
C2	0.0607 (11)	0.0428 (10)	0.0824 (13)	−0.0098 (8)	0.0189 (9)	−0.0067 (9)
C3	0.0704 (12)	0.0604 (12)	0.0614 (12)	−0.0067 (9)	0.0098 (9)	−0.0233 (9)
C4	0.0484 (8)	0.0589 (11)	0.0403 (8)	0.0030 (8)	0.0096 (7)	−0.0072 (7)
C5	0.0340 (7)	0.0411 (8)	0.0386 (7)	0.0026 (6)	0.0088 (6)	0.0006 (6)
C6	0.0425 (8)	0.0388 (8)	0.0402 (8)	0.0044 (6)	0.0126 (6)	0.0003 (6)
C7	0.0645 (11)	0.0929 (15)	0.0362 (9)	0.0050 (10)	0.0164 (8)	−0.0053 (9)
C8	0.0307 (7)	0.0476 (9)	0.0490 (8)	−0.0051 (6)	0.0068 (6)	0.0043 (7)
C9	0.0341 (7)	0.0446 (9)	0.0510 (9)	−0.0058 (6)	0.0095 (6)	0.0098 (7)
C10	0.0589 (10)	0.0556 (10)	0.0445 (9)	0.0084 (8)	0.0272 (7)	0.0085 (7)
C11	0.0410 (7)	0.0369 (8)	0.0481 (8)	0.0058 (6)	0.0221 (6)	0.0066 (6)
C12	0.0387 (8)	0.0456 (9)	0.0772 (12)	0.0017 (7)	0.0300 (8)	0.0100 (8)
C13	0.0307 (7)	0.0395 (9)	0.0805 (12)	−0.0024 (6)	0.0110 (7)	0.0025 (8)
C14	0.0396 (7)	0.0328 (8)	0.0494 (9)	0.0009 (6)	0.0035 (6)	−0.0035 (6)
C15	0.0376 (7)	0.0354 (7)	0.0399 (7)	0.0015 (6)	0.0132 (6)	0.0017 (6)
C16	0.0304 (6)	0.0311 (7)	0.0397 (7)	0.0020 (5)	0.0117 (5)	0.0027 (5)

O1—N1	1.223 (2)	C4—C7	1.416 (3)
O2—N1	1.220 (2)	C5—C6	1.391 (2)
O3—N6	1.216 (2)	C6—H6	0.9300
O4—N6	1.221 (2)	C7—H7	0.9300
N1—C1	1.474 (2)	C8—C9	1.520 (2)
N2—C7	1.309 (3)	C8—H8A	0.9700
N2—N3	1.3603 (18)	C8—H8B	0.9700
N3—C5	1.3643 (19)	C9—H9A	0.9700
N3—C8	1.445 (2)	C9—H9B	0.9700
N4—N5	1.3581 (17)	C10—C11	1.411 (2)
N4—C16	1.3650 (18)	C10—H10	0.9300
N4—C9	1.4494 (19)	C11—C12	1.402 (2)
N5—C10	1.316 (2)	C11—C16	1.4082 (19)
N6—C14	1.472 (2)	C12—C13	1.360 (2)
C1—C6	1.367 (2)	C12—H12	0.9300
C1—C2	1.404 (2)	C13—C14	1.401 (2)
C2—C3	1.361 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.373 (2)
C3—C4	1.400 (3)	C15—C16	1.3929 (19)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.406 (2)
O2—N1—O1	123.51 (18)	C4—C7—H7	123.8
O2—N1—C1	118.09 (18)	N3—C8—C9	111.77 (12)
O1—N1—C1	118.37 (15)	N3—C8—H8A	109.3
C7—N2—N3	105.94 (14)	C9—C8—H8A	109.3
N2—N3—C5	111.41 (13)	N3—C8—H8B	109.3
N2—N3—C8	119.09 (13)	C9—C8—H8B	109.3
C5—N3—C8	128.28 (12)	H8A—C8—H8B	107.9
N5—N4—C16	111.41 (11)	N4—C9—C8	111.39 (12)
N5—N4—C9	118.85 (11)	N4—C9—H9A	109.3
C16—N4—C9	129.58 (12)	C8—C9—H9A	109.3
C10—N5—N4	106.31 (12)	N4—C9—H9B	109.3
O3—N6—O4	123.09 (18)	C8—C9—H9B	109.3
O3—N6—C14	118.95 (15)	H9A—C9—H9B	108.0
O4—N6—C14	117.96 (18)	N5—C10—C11	111.71 (13)
C6—C1—C2	124.04 (16)	N5—C10—H10	124.1
C6—C1—N1	117.51 (15)	C11—C10—H10	124.1
C2—C1—N1	118.44 (16)	C12—C11—C16	119.62 (14)
C3—C2—C1	119.66 (17)	C12—C11—C10	136.07 (14)
C3—C2—H2	120.2	C16—C11—C10	104.29 (13)
C1—C2—H2	120.2	C13—C12—C11	118.78 (14)
C2—C3—C4	118.92 (16)	C13—C12—H12	120.6
C2—C3—H3	120.5	C11—C12—H12	120.6
C4—C3—H3	120.5	C12—C13—C14	119.75 (14)
C3—C4—C5	119.45 (16)	C12—C13—H13	120.1
C3—C4—C7	136.90 (17)	C14—C13—H13	120.1
C5—C4—C7	103.63 (16)	C15—C14—C13	124.32 (15)
N3—C5—C6	130.81 (13)	C15—C14—N6	117.30 (15)
N3—C5—C4	106.64 (13)	C13—C14—N6	118.38 (14)
C6—C5—C4	122.54 (15)	C14—C15—C16	114.97 (13)
C1—C6—C5	115.31 (14)	C14—C15—H15	122.5
C1—C6—H6	122.3	C16—C15—H15	122.5
C5—C6—H6	122.3	N4—C16—C15	131.16 (12)
N2—C7—C4	112.36 (15)	N4—C16—C11	106.28 (12)
N2—C7—H7	123.8	C15—C16—C11	122.54 (13)
C7—N2—N3—C5	1.38 (17)	C5—N3—C8—C9	87.72 (18)
C7—N2—N3—C8	169.77 (14)	N5—N4—C9—C8	−68.45 (17)
C16—N4—N5—C10	0.40 (17)	C16—N4—C9—C8	106.61 (16)
C9—N4—N5—C10	176.31 (14)	N3—C8—C9—N4	−65.19 (17)
O2—N1—C1—C6	−176.34 (16)	N4—N5—C10—C11	−0.10 (18)
O1—N1—C1—C6	5.4 (2)	N5—C10—C11—C12	177.90 (17)
O2—N1—C1—C2	5.0 (2)	N5—C10—C11—C16	−0.21 (18)
O1—N1—C1—C2	−173.22 (15)	C16—C11—C12—C13	0.6 (2)
C6—C1—C2—C3	−2.2 (3)	C10—C11—C12—C13	−177.33 (17)
N1—C1—C2—C3	176.39 (16)	C11—C12—C13—C14	−1.3 (2)
C1—C2—C3—C4	1.7 (3)	C12—C13—C14—C15	0.8 (2)
C2—C3—C4—C5	0.6 (3)	C12—C13—C14—N6	179.97 (14)
C2—C3—C4—C7	178.7 (2)	O3—N6—C14—C15	−7.5 (2)
N2—N3—C5—C6	−179.39 (14)	O4—N6—C14—C15	172.00 (16)
C8—N3—C5—C6	13.6 (2)	O3—N6—C14—C13	173.18 (16)
N2—N3—C5—C4	−0.72 (16)	O4—N6—C14—C13	−7.3 (2)
C8—N3—C5—C4	−167.77 (13)	C13—C14—C15—C16	0.6 (2)
C3—C4—C5—N3	178.52 (15)	N6—C14—C15—C16	−178.62 (12)
C7—C4—C5—N3	−0.18 (17)	N5—N4—C16—C15	−179.32 (14)
C3—C4—C5—C6	−2.7 (2)	C9—N4—C16—C15	5.3 (3)
C7—C4—C5—C6	178.62 (14)	N5—N4—C16—C11	−0.53 (15)
C2—C1—C6—C5	0.2 (2)	C9—N4—C16—C11	−175.88 (14)
N1—C1—C6—C5	−178.41 (12)	C14—C15—C16—N4	177.23 (14)
N3—C5—C6—C1	−179.27 (14)	C14—C15—C16—C11	−1.4 (2)
C4—C5—C6—C1	2.2 (2)	C12—C11—C16—N4	−178.06 (13)
N3—N2—C7—C4	−1.5 (2)	C10—C11—C16—N4	0.43 (15)
C3—C4—C7—N2	−177.3 (2)	C12—C11—C16—C15	0.9 (2)
C5—C4—C7—N2	1.1 (2)	C10—C11—C16—C15	179.35 (13)
N2—N3—C8—C9	−78.47 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N5i	0.93	2.48	3.344 (2)	154
C15—H15···O1i	0.93	2.47	3.401 (2)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N5i	0.93	2.48	3.344 (2)	154
C15—H15⋯O1i	0.93	2.47	3.401 (2)	179

Symmetry code: (i) .