Crystal structure of triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tri-carboxyl-ate.

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 carboxyl-ate 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, mol-ecules 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.

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 ▸).

Experimental

Crystal data

C19H23N3O8

M = 421.40

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.03

4233 reflections

309 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.25 e Å−3

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 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015017235/is5422sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S2056989015017235/is5422fig1.tif

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.

Click here for additional data file.

. DOI: 10.1107/S2056989015017235/is5422fig2.tif

A packing view of the title compound showing mol­ecules linked together by hydrogen bonds as dashed lines.

CCDC reference: 1424508

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

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

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1N2i	0.93	2.53	3.443(2)	168
C4H4O7ii	0.93	2.53	3.205(2)	129

Symmetry codes: (i) ; (ii) .