organic compounds
H-indazol-2-yl)propane-1,2,3-tricarboxylate
of triethyl 2-(5-nitro-2aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: mboulhaoua4@gmail.com
In the title compound, C19H23N3O8, the 5-nitro-2H-indazol-2-yl unit is almost planar, with the maximum deviation from the mean plane being 0.024 (2) Å. The fused-ring system is nearly perpendicular to the three carboxylate groups, with dihedral angles of 90.0 (3), 83.8 (1) and 80.4 (1)°. The ethyl groups attached to both ends of the propane chain are each disordered over two sets of sites, with site-occupancy ratios of 0.425 (17):0.575 (17) and 0.302 (15):0.698 (15). In the crystal, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers. The dimers are further linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.
CCDC reference: 1424508
1. Related literature
For the pharmacological and biochemical properties of indazoles and their derivatives, see: Abbassi et al. (2014); Li et al. (2003); Lee et al. (2001). For compounds with similar structures, see: El Brahmi et al. (2012); Chicha et al. (2013).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (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: 1424508
10.1107/S2056989015017235/is5422sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017235/is5422Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017235/is5422Isup3.cml
To a solution of 5-nitro-1H-indazole (0.5 g, 3 mmol) in THF (30 ml) was added ethyl bromoacetate (2 g, 12 mmol), potassium carbonate (1.24 g, 9 mmol) and a catalytic quantity of tetra-n-butylammonium iodide. The mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford the title compound as colourless crystals (yield: 66%; m.p. = 381 K).
The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic), 0.97 Å (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq (aromatic and methylene C) and 1.5Ueq(methyl C). The two ethyl groups attached to both ends of the propane chain are disordered with occupancy ratios of 0.425 (17):0.575 (17) and 0.302 (15):0.698 (15). The C11A—C12A, C11B—C12B, C15A—C16A and C15A—C16B distances were restrained to 1.483 (1) Å.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).C19H23N3O8 | F(000) = 888 |
Mr = 421.40 | Dx = 1.354 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.4555 (4) Å | Cell parameters from 4233 reflections |
b = 18.6185 (6) Å | θ = 2.7–26.4° |
c = 8.5258 (3) Å | µ = 0.11 mm−1 |
β = 104.603 (1)° | T = 296 K |
V = 2066.90 (12) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.31 × 0.26 mm |
Bruker X8 APEX diffractometer | 4233 independent reflections |
Radiation source: fine-focus sealed tube | 3523 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 26.4°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −16→16 |
Tmin = 0.673, Tmax = 0.746 | k = −23→23 |
36533 measured reflections | l = −10→10 |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.8225P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
4233 reflections | Δρmax = 0.30 e Å−3 |
309 parameters | Δρmin = −0.25 e Å−3 |
C19H23N3O8 | V = 2066.90 (12) Å3 |
Mr = 421.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4555 (4) Å | µ = 0.11 mm−1 |
b = 18.6185 (6) Å | T = 296 K |
c = 8.5258 (3) Å | 0.42 × 0.31 × 0.26 mm |
β = 104.603 (1)° |
Bruker X8 APEX diffractometer | 4233 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3523 reflections with I > 2σ(I) |
Tmin = 0.673, Tmax = 0.746 | Rint = 0.031 |
36533 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 4 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.30 e Å−3 |
4233 reflections | Δρmin = −0.25 e Å−3 |
309 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.57273 (14) | 0.40719 (9) | 0.4318 (2) | 0.0514 (4) | |
H1 | 0.5740 | 0.4566 | 0.4170 | 0.062* | |
C2 | 0.63996 (13) | 0.36345 (10) | 0.3833 (2) | 0.0510 (4) | |
H2 | 0.6882 | 0.3830 | 0.3344 | 0.061* | |
C3 | 0.63713 (11) | 0.28818 (9) | 0.4066 (2) | 0.0423 (4) | |
C4 | 0.56810 (11) | 0.25484 (8) | 0.4740 (2) | 0.0392 (3) | |
H4 | 0.5675 | 0.2052 | 0.4859 | 0.047* | |
C5 | 0.49768 (11) | 0.29933 (8) | 0.52479 (18) | 0.0340 (3) | |
C6 | 0.50052 (11) | 0.37504 (8) | 0.5058 (2) | 0.0385 (3) | |
C7 | 0.41751 (11) | 0.28790 (8) | 0.59778 (19) | 0.0360 (3) | |
H7 | 0.3948 | 0.2439 | 0.6272 | 0.043* | |
C8 | 0.29510 (11) | 0.37241 (8) | 0.69122 (19) | 0.0352 (3) | |
C9 | 0.22024 (12) | 0.42301 (8) | 0.5780 (2) | 0.0395 (3) | |
H9A | 0.1699 | 0.4399 | 0.6332 | 0.047* | |
H9B | 0.2579 | 0.4645 | 0.5551 | 0.047* | |
C10 | 0.16487 (13) | 0.38884 (9) | 0.4201 (2) | 0.0451 (4) | |
C11A | 0.0301 (7) | 0.4160 (8) | 0.1824 (13) | 0.074 (3) | 0.425 (17) |
H11A | 0.0590 | 0.3764 | 0.1346 | 0.088* | 0.425 (17) |
H11B | 0.0330 | 0.4596 | 0.1212 | 0.088* | 0.425 (17) |
C12A | −0.0758 (10) | 0.4003 (13) | 0.194 (2) | 0.130 (6) | 0.425 (17) |
H12A | −0.1191 | 0.3917 | 0.0876 | 0.195* | 0.425 (17) |
H12B | −0.1018 | 0.4405 | 0.2419 | 0.195* | 0.425 (17) |
H12C | −0.0752 | 0.3585 | 0.2601 | 0.195* | 0.425 (17) |
C11B | 0.0141 (6) | 0.3852 (5) | 0.2097 (12) | 0.075 (2) | 0.575 (17) |
H11C | 0.0492 | 0.3815 | 0.1236 | 0.090* | 0.575 (17) |
H11D | −0.0005 | 0.3371 | 0.2415 | 0.090* | 0.575 (17) |
C12B | −0.0826 (6) | 0.4264 (6) | 0.1532 (14) | 0.089 (3) | 0.575 (17) |
H12D | −0.1247 | 0.4041 | 0.0579 | 0.134* | 0.575 (17) |
H12E | −0.0669 | 0.4747 | 0.1281 | 0.134* | 0.575 (17) |
H12F | −0.1187 | 0.4272 | 0.2369 | 0.134* | 0.575 (17) |
C13 | 0.24285 (12) | 0.30296 (8) | 0.7280 (2) | 0.0393 (3) | |
H13A | 0.2198 | 0.2751 | 0.6293 | 0.047* | |
H13B | 0.2920 | 0.2742 | 0.8055 | 0.047* | |
C14 | 0.15273 (14) | 0.32020 (10) | 0.7957 (2) | 0.0503 (4) | |
C15A | −0.0178 (6) | 0.3478 (8) | 0.7695 (11) | 0.057 (3) | 0.302 (15) |
H15A | −0.0369 | 0.3170 | 0.8488 | 0.069* | 0.302 (15) |
H15B | 0.0080 | 0.3931 | 0.8198 | 0.069* | 0.302 (15) |
C16A | −0.1043 (10) | 0.3585 (16) | 0.6243 (16) | 0.107 (7) | 0.302 (15) |
H16A | −0.1639 | 0.3741 | 0.6574 | 0.161* | 0.302 (15) |
H16B | −0.1191 | 0.3140 | 0.5661 | 0.161* | 0.302 (15) |
H16C | −0.0858 | 0.3942 | 0.5555 | 0.161* | 0.302 (15) |
C15B | −0.0333 (4) | 0.3135 (4) | 0.7256 (9) | 0.0766 (16) | 0.698 (15) |
H15C | −0.0248 | 0.3055 | 0.8406 | 0.092* | 0.698 (15) |
H15D | −0.0797 | 0.2773 | 0.6663 | 0.092* | 0.698 (15) |
C16B | −0.0756 (7) | 0.3862 (2) | 0.6799 (14) | 0.106 (3) | 0.698 (15) |
H16D | −0.1443 | 0.3888 | 0.6929 | 0.158* | 0.698 (15) |
H16E | −0.0763 | 0.3957 | 0.5690 | 0.158* | 0.698 (15) |
H16F | −0.0335 | 0.4213 | 0.7485 | 0.158* | 0.698 (15) |
C17 | 0.34844 (12) | 0.40826 (9) | 0.8553 (2) | 0.0423 (4) | |
C18 | 0.35337 (18) | 0.50899 (12) | 1.0282 (3) | 0.0682 (6) | |
H18A | 0.4263 | 0.4989 | 1.0649 | 0.082* | |
H18B | 0.3451 | 0.5605 | 1.0131 | 0.082* | |
C19 | 0.3021 (2) | 0.48556 (16) | 1.1524 (3) | 0.0839 (7) | |
H19A | 0.3314 | 0.5103 | 1.2521 | 0.126* | |
H19B | 0.3112 | 0.4347 | 1.1690 | 0.126* | |
H19C | 0.2301 | 0.4963 | 1.1172 | 0.126* | |
N1 | 0.71300 (11) | 0.24372 (9) | 0.3546 (2) | 0.0561 (4) | |
N2 | 0.42831 (10) | 0.40789 (7) | 0.56357 (18) | 0.0432 (3) | |
N3 | 0.37965 (9) | 0.35279 (6) | 0.61715 (15) | 0.0346 (3) | |
O1 | 0.71038 (13) | 0.17910 (8) | 0.3693 (2) | 0.0810 (5) | |
O2 | 0.77500 (13) | 0.27406 (10) | 0.2951 (3) | 0.0952 (6) | |
O3 | 0.19189 (12) | 0.33658 (8) | 0.36163 (16) | 0.0686 (4) | |
O4 | 0.08034 (11) | 0.42484 (9) | 0.35264 (18) | 0.0758 (5) | |
O5 | 0.16075 (13) | 0.34111 (10) | 0.9308 (2) | 0.0840 (5) | |
O6 | 0.06455 (10) | 0.30905 (10) | 0.6864 (2) | 0.0762 (5) | |
O7 | 0.41569 (11) | 0.37912 (8) | 0.95228 (17) | 0.0683 (4) | |
O8 | 0.31115 (10) | 0.47256 (6) | 0.87260 (15) | 0.0528 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0514 (10) | 0.0374 (8) | 0.0739 (12) | −0.0036 (7) | 0.0316 (9) | 0.0027 (8) |
C2 | 0.0439 (9) | 0.0520 (10) | 0.0651 (12) | −0.0052 (7) | 0.0285 (8) | −0.0004 (8) |
C3 | 0.0330 (7) | 0.0481 (9) | 0.0468 (9) | 0.0030 (6) | 0.0119 (7) | −0.0071 (7) |
C4 | 0.0356 (7) | 0.0352 (7) | 0.0467 (9) | 0.0034 (6) | 0.0105 (7) | −0.0024 (6) |
C5 | 0.0322 (7) | 0.0320 (7) | 0.0378 (8) | −0.0002 (5) | 0.0083 (6) | −0.0012 (6) |
C6 | 0.0372 (7) | 0.0327 (7) | 0.0484 (9) | −0.0008 (6) | 0.0160 (7) | −0.0011 (6) |
C7 | 0.0378 (7) | 0.0283 (7) | 0.0439 (8) | 0.0015 (6) | 0.0138 (6) | 0.0009 (6) |
C8 | 0.0351 (7) | 0.0319 (7) | 0.0418 (8) | 0.0014 (6) | 0.0159 (6) | −0.0019 (6) |
C9 | 0.0394 (8) | 0.0355 (7) | 0.0467 (9) | 0.0060 (6) | 0.0169 (7) | 0.0002 (6) |
C10 | 0.0455 (9) | 0.0487 (9) | 0.0429 (9) | 0.0099 (7) | 0.0148 (7) | 0.0025 (7) |
C11A | 0.077 (5) | 0.086 (7) | 0.051 (4) | 0.022 (4) | 0.004 (3) | 0.000 (4) |
C12A | 0.091 (9) | 0.213 (17) | 0.077 (8) | −0.061 (9) | 0.004 (6) | −0.018 (9) |
C11B | 0.068 (4) | 0.084 (5) | 0.058 (4) | 0.025 (3) | −0.013 (3) | −0.017 (3) |
C12B | 0.065 (4) | 0.116 (5) | 0.077 (5) | 0.025 (3) | −0.003 (3) | −0.002 (3) |
C13 | 0.0410 (8) | 0.0362 (8) | 0.0442 (9) | −0.0024 (6) | 0.0172 (7) | 0.0010 (6) |
C14 | 0.0526 (10) | 0.0478 (9) | 0.0591 (11) | −0.0020 (8) | 0.0302 (9) | 0.0079 (8) |
C15A | 0.042 (4) | 0.066 (7) | 0.073 (5) | 0.001 (4) | 0.031 (4) | 0.001 (4) |
C16A | 0.050 (6) | 0.177 (19) | 0.095 (9) | 0.008 (8) | 0.020 (5) | 0.029 (10) |
C15B | 0.048 (2) | 0.082 (3) | 0.111 (4) | −0.005 (2) | 0.039 (2) | −0.005 (3) |
C16B | 0.078 (5) | 0.103 (4) | 0.152 (8) | 0.031 (3) | 0.058 (5) | 0.012 (4) |
C17 | 0.0384 (8) | 0.0414 (8) | 0.0496 (9) | −0.0001 (6) | 0.0156 (7) | −0.0072 (7) |
C18 | 0.0766 (14) | 0.0605 (12) | 0.0694 (14) | −0.0083 (10) | 0.0222 (11) | −0.0304 (10) |
C19 | 0.0993 (18) | 0.0977 (18) | 0.0555 (13) | 0.0002 (15) | 0.0214 (13) | −0.0182 (12) |
N1 | 0.0420 (8) | 0.0628 (10) | 0.0689 (11) | 0.0059 (7) | 0.0240 (7) | −0.0085 (8) |
N2 | 0.0454 (7) | 0.0288 (6) | 0.0626 (9) | −0.0017 (5) | 0.0269 (7) | 0.0016 (6) |
N3 | 0.0353 (6) | 0.0278 (6) | 0.0440 (7) | 0.0005 (5) | 0.0163 (5) | 0.0008 (5) |
O1 | 0.0826 (11) | 0.0582 (9) | 0.1184 (14) | 0.0257 (8) | 0.0552 (10) | 0.0049 (9) |
O2 | 0.0723 (10) | 0.0863 (12) | 0.1535 (18) | −0.0031 (9) | 0.0777 (12) | −0.0181 (11) |
O3 | 0.0801 (10) | 0.0674 (9) | 0.0513 (8) | 0.0270 (7) | 0.0039 (7) | −0.0158 (7) |
O4 | 0.0639 (9) | 0.0976 (11) | 0.0563 (8) | 0.0383 (8) | −0.0025 (7) | −0.0173 (8) |
O5 | 0.0877 (11) | 0.1046 (13) | 0.0768 (11) | −0.0112 (9) | 0.0526 (9) | −0.0237 (9) |
O6 | 0.0411 (7) | 0.1151 (13) | 0.0780 (10) | 0.0068 (7) | 0.0252 (7) | 0.0200 (9) |
O7 | 0.0600 (8) | 0.0730 (9) | 0.0603 (8) | 0.0205 (7) | −0.0067 (7) | −0.0192 (7) |
O8 | 0.0645 (8) | 0.0419 (6) | 0.0531 (7) | 0.0044 (5) | 0.0169 (6) | −0.0119 (5) |
C1—C2 | 1.357 (2) | C12B—H12D | 0.9600 |
C1—C6 | 1.418 (2) | C12B—H12E | 0.9600 |
C1—H1 | 0.9300 | C12B—H12F | 0.9600 |
C2—C3 | 1.417 (2) | C13—C14 | 1.503 (2) |
C2—H2 | 0.9300 | C13—H13A | 0.9700 |
C3—C4 | 1.359 (2) | C13—H13B | 0.9700 |
C3—N1 | 1.467 (2) | C14—O5 | 1.195 (2) |
C4—C5 | 1.407 (2) | C14—O6 | 1.327 (2) |
C4—H4 | 0.9300 | C15A—C16A | 1.4828 (10) |
C5—C7 | 1.391 (2) | C15A—O6 | 1.627 (10) |
C5—C6 | 1.420 (2) | C15A—H15A | 0.9700 |
C6—N2 | 1.3424 (19) | C15A—H15B | 0.9700 |
C7—N3 | 1.3375 (18) | C16A—H16A | 0.9600 |
C7—H7 | 0.9300 | C16A—H16B | 0.9600 |
C8—N3 | 1.4794 (18) | C16A—H16C | 0.9600 |
C8—C9 | 1.531 (2) | C15B—O6 | 1.440 (4) |
C8—C13 | 1.541 (2) | C15B—C16B | 1.4825 (10) |
C8—C17 | 1.553 (2) | C15B—H15C | 0.9700 |
C9—C10 | 1.506 (2) | C15B—H15D | 0.9700 |
C9—H9A | 0.9700 | C16B—H16D | 0.9600 |
C9—H9B | 0.9700 | C16B—H16E | 0.9600 |
C10—O3 | 1.191 (2) | C16B—H16F | 0.9600 |
C10—O4 | 1.320 (2) | C17—O7 | 1.191 (2) |
C11A—O4 | 1.448 (11) | C17—O8 | 1.3205 (19) |
C11A—C12A | 1.4826 (10) | C18—C19 | 1.468 (3) |
C11A—H11A | 0.9700 | C18—O8 | 1.471 (2) |
C11A—H11B | 0.9700 | C18—H18A | 0.9700 |
C12A—H12A | 0.9600 | C18—H18B | 0.9700 |
C12A—H12B | 0.9600 | C19—H19A | 0.9600 |
C12A—H12C | 0.9600 | C19—H19B | 0.9600 |
C11B—C12B | 1.4824 (10) | C19—H19C | 0.9600 |
C11B—O4 | 1.508 (8) | N1—O1 | 1.211 (2) |
C11B—H11C | 0.9700 | N1—O2 | 1.219 (2) |
C11B—H11D | 0.9700 | N2—N3 | 1.3567 (17) |
C2—C1—C6 | 117.83 (15) | C14—C13—C8 | 110.65 (13) |
C2—C1—H1 | 121.1 | C14—C13—H13A | 109.5 |
C6—C1—H1 | 121.1 | C8—C13—H13A | 109.5 |
C1—C2—C3 | 120.47 (15) | C14—C13—H13B | 109.5 |
C1—C2—H2 | 119.8 | C8—C13—H13B | 109.5 |
C3—C2—H2 | 119.8 | H13A—C13—H13B | 108.1 |
C4—C3—C2 | 123.80 (14) | O5—C14—O6 | 125.14 (18) |
C4—C3—N1 | 118.15 (15) | O5—C14—C13 | 123.66 (18) |
C2—C3—N1 | 118.05 (15) | O6—C14—C13 | 111.21 (16) |
C3—C4—C5 | 116.51 (14) | C16A—C15A—O6 | 100.0 (12) |
C3—C4—H4 | 121.7 | C16A—C15A—H15A | 111.8 |
C5—C4—H4 | 121.7 | O6—C15A—H15A | 111.8 |
C7—C5—C4 | 134.93 (14) | C16A—C15A—H15B | 111.8 |
C7—C5—C6 | 104.42 (12) | O6—C15A—H15B | 111.8 |
C4—C5—C6 | 120.65 (13) | H15A—C15A—H15B | 109.5 |
N2—C6—C1 | 127.71 (14) | C15A—C16A—H16A | 109.5 |
N2—C6—C5 | 111.56 (13) | C15A—C16A—H16B | 109.5 |
C1—C6—C5 | 120.72 (14) | H16A—C16A—H16B | 109.5 |
N3—C7—C5 | 106.23 (12) | C15A—C16A—H16C | 109.5 |
N3—C7—H7 | 126.9 | H16A—C16A—H16C | 109.5 |
C5—C7—H7 | 126.9 | H16B—C16A—H16C | 109.5 |
N3—C8—C9 | 109.71 (12) | O6—C15B—C16B | 107.7 (4) |
N3—C8—C13 | 108.61 (11) | O6—C15B—H15C | 110.2 |
C9—C8—C13 | 112.54 (12) | C16B—C15B—H15C | 110.2 |
N3—C8—C17 | 105.09 (11) | O6—C15B—H15D | 110.2 |
C9—C8—C17 | 112.63 (12) | C16B—C15B—H15D | 110.2 |
C13—C8—C17 | 107.94 (13) | H15C—C15B—H15D | 108.5 |
C10—C9—C8 | 113.73 (13) | C15B—C16B—H16D | 109.5 |
C10—C9—H9A | 108.8 | C15B—C16B—H16E | 109.5 |
C8—C9—H9A | 108.8 | H16D—C16B—H16E | 109.5 |
C10—C9—H9B | 108.8 | C15B—C16B—H16F | 109.5 |
C8—C9—H9B | 108.8 | H16D—C16B—H16F | 109.5 |
H9A—C9—H9B | 107.7 | H16E—C16B—H16F | 109.5 |
O3—C10—O4 | 123.57 (17) | O7—C17—O8 | 125.39 (16) |
O3—C10—C9 | 125.79 (15) | O7—C17—C8 | 121.80 (14) |
O4—C10—C9 | 110.64 (14) | O8—C17—C8 | 112.81 (14) |
O4—C11A—C12A | 99.7 (9) | C19—C18—O8 | 111.62 (18) |
O4—C11A—H11A | 111.8 | C19—C18—H18A | 109.3 |
C12A—C11A—H11A | 111.8 | O8—C18—H18A | 109.3 |
O4—C11A—H11B | 111.8 | C19—C18—H18B | 109.3 |
C12A—C11A—H11B | 111.8 | O8—C18—H18B | 109.3 |
H11A—C11A—H11B | 109.5 | H18A—C18—H18B | 108.0 |
C11A—C12A—H12A | 109.5 | C18—C19—H19A | 109.5 |
C11A—C12A—H12B | 109.5 | C18—C19—H19B | 109.5 |
H12A—C12A—H12B | 109.5 | H19A—C19—H19B | 109.5 |
C11A—C12A—H12C | 109.5 | C18—C19—H19C | 109.5 |
H12A—C12A—H12C | 109.5 | H19A—C19—H19C | 109.5 |
H12B—C12A—H12C | 109.5 | H19B—C19—H19C | 109.5 |
C12B—C11B—O4 | 107.5 (7) | O1—N1—O2 | 122.96 (16) |
C12B—C11B—H11C | 110.2 | O1—N1—C3 | 119.26 (15) |
O4—C11B—H11C | 110.2 | O2—N1—C3 | 117.76 (16) |
C12B—C11B—H11D | 110.2 | C6—N2—N3 | 103.56 (12) |
O4—C11B—H11D | 110.2 | C7—N3—N2 | 114.22 (12) |
H11C—C11B—H11D | 108.5 | C7—N3—C8 | 129.31 (12) |
C11B—C12B—H12D | 109.5 | N2—N3—C8 | 116.45 (11) |
C11B—C12B—H12E | 109.5 | C10—O4—C11A | 120.8 (5) |
H12D—C12B—H12E | 109.5 | C10—O4—C11B | 111.8 (3) |
C11B—C12B—H12F | 109.5 | C14—O6—C15B | 122.4 (4) |
H12D—C12B—H12F | 109.5 | C14—O6—C15A | 102.2 (4) |
H12E—C12B—H12F | 109.5 | C17—O8—C18 | 116.58 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N2i | 0.93 | 2.53 | 3.443 (2) | 168 |
C4—H4···O7ii | 0.93 | 2.53 | 3.205 (2) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N2i | 0.93 | 2.53 | 3.443 (2) | 168 |
C4—H4···O7ii | 0.93 | 2.53 | 3.205 (2) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) 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 and University Mohammed V, Rabat, Morocco, for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Recently, a number of pharmacological tests revealed that the indazole derivatives present various biological activities and other chemical industries. With respect to biological applications, these derivatives are found potent anti-tumour (Abbassi et al., 2014), anti-microbial (Li et al., 2003) and anti-platelet (Lee et al., 2001). As a continuation of our research work devoted to the development of N-substituted indazole and trying potential pharmacological activities (El Brahmi et al., 2012; Chicha et al., 2013), we have studied the reaction of ethyl bromoacetate towards 5-nitro-1H-indazole under phase-transfer catalysis conditions using tetra-n-butylammonium iodide (TBAI) as catalyst and potassium carbonate as base. The title compound was isolated and its structure was established.
The molecule of the title compound is build up from two fused five- and six-membered rings linked to a nitro group and to propane-1,2,3-tricarboxylate, which are connected to three ethyl moieties as shown in Fig. 1. The two ethyl groups attached to both ends of the propane chain are each split with occupancy ratios of 0.425 (17) (Cl1A–C12A) : 0.575 (17) (Cl1B–C12B) and 0.302 (15) (C15A–C16A) : 0.698 (15) (C15B–C16B). The fused ring system is virtually planar with the largest deviation from the mean plane being 0.013 (2) Å at N2 and makes dihedral angles of 83.8 (1), 80.5 (1) and 90.0 (3)° with the three carboxylate groups (C10/O3/O4), (C14/O/5O6) and (C17/O7/O8), respectively. In the crystal, the molecules are linked together by non-classic hydrogen bonds, forming a three dimensional network (Fig. 2 and Table 1).