Crystal structure of triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tri­carboxyl­ate

Boulhaoua, M.; Benchidmi, M.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S2056989015017235

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o780-o781

doi:10.1107/S2056989015017235

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Crystal structure of triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tricarboxylate

Mohammed Boulhaoua,^a ^* Mohammed Benchidmi,^a El Mokhtar Essassi,^a Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire 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

Edited by H. Ishida, Okayama University, Japan (Received 10 September 2015; accepted 15 September 2015; online 26 September 2015)

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.

Keywords: crystal structure; indazole; ester; pharmacological properties; biochemical properties.

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

C₁₉H₂₃N₃O₈
M_r = 421.40
Monoclinic, P 2₁ /c
a = 13.4555 (4) Å
b = 18.6185 (6) Å
c = 8.5258 (3) Å
β = 104.603 (1)°
V = 2066.90 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.42 × 0.31 × 0.26 mm

2.2. Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.673, T_max = 0.746
36533 measured reflections
4233 independent reflections
3523 reflections with I > 2σ(I)
R_int = 0.031

2.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.03
4233 reflections
309 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015017235/is5422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015017235/is5422Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015017235/is5422Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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).

Experimental top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. A packing view of the title compound showing molecules linked together by hydrogen bonds as dashed lines.

Triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tricarboxylate top

Crystal data top

C₁₉H₂₃N₃O₈	F(000) = 888
M_r = 421.40	D_x = 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

Data collection top

Bruker X8 APEX diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	3523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.673, T_max = 0.746	k = −23→23
36533 measured reflections	l = −10→10

Refinement top

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(F_o²) + (0.0586P)² + 0.8225P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.003
4233 reflections	Δρ_max = 0.30 e Å⁻³
309 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₂₃N₃O₈	V = 2066.90 (12) Å³
M_r = 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)°

Data collection top

Bruker X8 APEX diffractometer	4233 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3523 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.746	R_int = 0.031
36533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	4 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
4233 reflections	Δρ_min = −0.25 e Å⁻³
309 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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Volume 71| Part 10| October 2015| Pages o780-o781

doi:10.1107/S2056989015017235

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of tri­ethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tri­carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tricarboxylate