organic compounds
6,6′-Dinitro-1,1′-(ethane-1,2-diyl)di(1H-indazole)
aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: assoman_k@yahoo.fr
The molecule of the title compound, C16H12N6O4, is built up from two fused five- and six-membered rings linked by an ethylene 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, molecules are linked by C—H⋯N and C—H⋯O hydrogen bonds into chains running parallel to the c axis.
CCDC reference: 988920
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
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Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
CCDC reference: 988920
10.1107/S1600536814004516/rz5107sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004516/rz5107Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814004516/rz5107Isup3.cml
A solution of 6-nitroindazole (0.5 g, 3.06 mmol) and KOH (0.17 g, 3.08 mmol) in EtOH (15 ml) was heated under reflux for 48 h. The mixture was cooled and the solvent removed from the filtrate in vacuo. The formed 6-nitroindazole potassium salt and 1,2-ethylene dibromide (0.27 ml, 1.48 mmol) was heated in dimethylformamide (5 ml) under reflux for 3 h. The mixture was then cooled, all volatiles were removed in vacuo and water was added. The precipitate was filtered and was purified by
(EtOAc/hexane 2:8 v/v). The title compound was recrystallized from acetone (yield: 35%; m. p.: 468 K).H atoms were located in a difference Fourier map and treated as riding, with C–H = 0.93-0.97 Å and with Uiso(H) = 1.2 Ueq(C). One outlier (0 1 1) was omitted in the last cycles of refinement.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).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) |
C16H12N6O4 | V = 1588.9 (12) Å3 |
Mr = 352.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.410 (5) Å | µ = 0.11 mm−1 |
b = 12.064 (5) Å | T = 296 K |
c = 14.804 (4) Å | 0.37 × 0.32 × 0.26 mm |
β = 109.01 (2)° |
Bruker X8 APEX diffractometer | 2667 reflections with I > 2σ(I) |
16446 measured reflections | Rint = 0.033 |
3503 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.20 e Å−3 |
3503 reflections | Δρmin = −0.19 e Å−3 |
236 parameters |
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 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···N5i | 0.93 | 2.48 | 3.344 (2) | 154.4 |
C15—H15···O1i | 0.93 | 2.47 | 3.401 (2) | 178.7 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
References
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Indazole moiety have been nucleus is a pharmaceutically important and emerging heterocycle with a broad spectrum of activities including anti-microbial1, anti-cancer, anti-inflammatory, anti- platelet, and selective 5-HT6 antagonists (Ali et al., 2012; Abbassi et al., 2012; Plescia et al., 2010; Lee et al., 2001; Liu et al., 2011). The present work is a continuation of the investigation on the indazole derivatives published recently by our team (Kouakou et al., 2013; Chicha et al., 2013).
The molecule of the title compound is formed by two fused five- and six-membered rings linked by an ethylene group and connected to two nitro groups as shown in Fig. 1. The two fused ring systems (N2/N3/C1–C7 and N4/N5C10–C16) make dihedral angles of 7.2 (2)° and 8.5 (2)° with the planes through the attached nitro groups (N1/O1/O2 and N6/O3(O4), respectively. The dihedral angle between the indazole ring systems is 39.74 (5)°. In the crystal, molecules are linked by C7—H7···N5 and C15—H15···O1 hydrogen interactions (Table 1) into chains running parallel to the [0 0 1] direction as shown in Fig. 2.