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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o1036-o1037
https://doi.org/10.1107/S2056989015023452

Crystal structure of 13-phenyl-2,3,4,13-tetra­hydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione

Esma Lamera,a Saida Benzerka,b Abdelmalek Bouraiou,a Sofiane Bouacida,a,c* Hocine Merazig,a Aissa Chibani,a Marc Le Borgned and Zouhair Bouazizd

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale CHEMS, Université des Frères Mentouri, Constantine 25000, Algeria, bLaboratoire de Synthèse des Molécules d'Intérêts Biologiques, Université des Frères Mentouri, Constantine 25000, Algeria, cDépartement Sciences de la Matière, Université Oum El Bouaghi, 04000, Algeria, and dUniversité de Lyon, Université Lyon 1, Faculté de Pharmacie, ISPB, EA 4446 Biomolécules Cancer et Chimiorésistances, SFR Santé Lyon-Est CNRS UMS3453-INSERM US7, 8 Avenue Rockefeller, F-69373 Lyon Cedex 8, France
*Correspondence e-mail: bouacida_sofiane@yahoo.fr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 3 December 2015; accepted 6 December 2015; online 12 December 2015)

The title compound, C21H16N2O3, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system (r.m.s. deviation = 0.018 Å). The phenyl ring is almost normal to the mean plane of the five-membered ring of the indazolone moiety, making a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety has an envelope conformation, with the central methyl­ene C atom as the flap. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming slabs parallel to the bc plane. The slabs are linked via C—H⋯π and π–π inter­actions [the shortest inter-centroid distance involving rings of pyrazolo­phthalazine moieties is 3.6430 (8) Å], forming a three-dimensional structure.

CCDC reference: 1440831

Similar articles

1. Related literature

For application of phthalazine derivatives see: Mosaddegh & Hassankhani (2011[Mosaddegh, E. & Hassankhani, A. (2011). Tetrahedron Lett. 52, 488-490.]); Hasaninejed et al. (2012[Hasaninejed, A., Kazerooni, M. R. & Zare, A. (2012). Catal. Today, 196, 148-155.]); Keshipour et al. (2012[Keshipour, S., Shojaei, S. & Shaabani, A. (2012). Tetrahedron, 68, 6141-6145.]). For the synthesis of this class of compounds, see: Carling et al. (2004[Carling, R. W., Moore, K. W., Street, L. J., Wild, D., Isted, C., Leeson, P. D., Thomas, S., O'Connor, D., McKernan, R. M., Quirk, K., Cook, S. M., Atack, J. R., Wafford, K. A., Thompson, S. A., Dawson, G. R., Ferris, P. & Castro, J. L. (2004). J. Med. Chem. 47, 1807-1822.]); Cashman & Ghirmai (2009[Cashman, J. R. & Ghirmai, S. (2009). Bioorg. Med. Chem. 17, 6890-6897.]); Hall et al. (1992[Hall, I. H., Hall, E. S. & Wong, O. T. (1992). Anticancer Drugs, 3, 55-62.], 2001[Hall, I. H., Covington, D. W., Wheaton, J. R., Izydore, R. A. & Zhou, X. (2001). Pharmazie, 56, 168-174.]); Bouraiou et al. (2015[Bouraiou, A., Bouacida, S., Merazig, H., Chibani, A. & Bouaziz, Z. (2015). Acta Cryst. E71, o604-o605.]); Nomoto et al. (1990[Nomoto, Y., Obase, H., Takai, H., Teranishi, M., Nakamura, J. & Kubo, K. (1990). Chem. Pharm. Bull. 38, 2179-2183.]). For the synthesis of the title compound, see: Bouraiou et al. (2015[Bouraiou, A., Bouacida, S., Merazig, H., Chibani, A. & Bouaziz, Z. (2015). Acta Cryst. E71, o604-o605.]); Khurana & Magoo (2009[Khurana, J. M. & Magoo, D. (2009). Tetrahedron Lett. 50, 7300-7303.]); Nagarapu et al. (2009[Nagarapu, L., Bantu, R. & Mereyala, H. B. (2009). J. Heterocycl. Chem. 46, 728-731.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H16N2O3

  • Mr = 344.36

  • Monoclinic, P 21 /c

  • a = 8.9028 (2) Å

  • b = 11.4507 (3) Å

  • c = 17.0274 (4) Å

  • β = 104.618 (1)°

  • V = 1679.64 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 295 K

  • 0.13 × 0.09 × 0.05 mm

2.2. Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.986

  • 4873 measured reflections

  • 4873 independent reflections

  • 3617 reflections with I > 2σ(I)

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.182

  • S = 1.12

  • 4873 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.6 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C2–C7 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O2i 0.93 2.59 3.488 (2) 163
C9—H9⋯O3ii 0.98 2.54 3.501 (2) 165
C18—H18⋯Cg3iii 0.93 2.68 3.552 (2) 156
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 1440831

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023452/su5255sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023452/su5255Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023452/su5255Isup3.cml

checkCIF report


Comments top

Phthalazine derivatives have been reported to act as anti­convulsants (Carling et al. 2004), potential inhibitors of serotonin reuptake (Cashman & Ghirmai, 2009), anti-proliferative agents against different human and murine tumor cells (Hall et al., 1992, 2001) and vasorelaxant agents (Nomoto et al. 1990). Therefore, a number of synthetic methods have been developed in recent years to uncover a variety of new reagents for the synthesis of phthalazine derivatives (Mosaddegh & Hassankhani, 2011; Hasaninejed et al., 2012; Keshipour et al., 2012). In previous work, we have reported the synthesis and structure heterocyclic compounds bearing a phthalazine unit (Bouraiou et al., 2015). Herein, we describe the synthesis and crystal structure of the title indazolo phthalazine-trione derivative, resulting from the reaction of phthalhydrazide, cyclo­hexa-1,3-dione and benzaldehyde in the presence of catalytic amounts of sulfuric acid.

The title compound, Fig. 1, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system [r.m.s. deviation = 0.018 Å]. The phenyl ring (C16—C21) is almost normal to the mean plane of the five-membered ring (N1/N2/C9/C10/C15) of the indazolone moiety with a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety (C10—C15) has an envelope conformation with the central methyl­ene C atom, C13, as the flap.

In the crystal, molecules are linked via C—H···O hydrogen bonds forming slabs parallel to the bc plane (Table 1 and Fig. 2). The slabs are linked via C—H···π (Table 1) and slipped parallel π-π inter­actions [the shortest inter-centroid distance involves Cg2···Cg3i = 3.6430 (8) Å; Cg2 and Cg3 are the centroids of rings (N1/N2/C1/C2/C7/C8) and (C2—C7), respectively; inter-planar distance = 3.457 (5); slippage = 1.07 Å; symmetry code: (i) -x+1, -y, -z], forming a three-dimensional structure.

Synthesis and crystallization top

The title compound was synthesized in accordance with established methods (Khurana & Magoo, 2009; Bouraiou et al., 2015). Spectroscopic results and physical properties are in agreement with literature reports (Nagarapu et al., 2009). The solid obtained, was recrystallized in a hot CHCl3/EtOAc/EtOH (1:1:1) mixture giving yellow crystals of the title compound. MS (ES-API): m/z [M+H]+ = 345.1; 1H-NMR δ (ppm) (250 MHz, CDCl3): 8.35–8.23 (m, 2H), 7.88–7.84 (m, 2H), 7.32–7.30 (m, 5H), 6.46 (s, 1H), 3.63–3.30 (m, 2H), 2.51–2.46 (m, 2H), 2.32–2.22 (m, 2H); 13C-NMR δ (ppm) (62.9 MHz, 3): 192.6, 156.1, 154.3, 152.3, 136.4, 134.6, 133.6, 129.1, 129.0, 128.7, 128.0, 127.8, 127.2, 119.7, 65.0, 37.0, 24.6, 22.3.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were located in difference Fourier maps but introduced in calculated positions and refined as riding atoms: C—H = 0.93-0.98 Å with Uiso(H) = 1.2 Ueq(C).

Related literature top

For application of phthalazine derivatives see: Mosaddegh & Hassankhani (2011); Hasaninejed et al. (2012); Keshipour et al. (2012). For the synthesis of this class of compounds, see: Carling et al. (2004); Cashman & Ghirmai (2009); Hall et al. (1992, 2001); Bouraiou et al. (2015); Nomoto et al. (1990). For the synthesis of the title compound, see: Bouraiou et al. (2015); Khurana & Magoo (2009); Nagarapu et al. (2009).

Structure description top

Phthalazine derivatives have been reported to act as anti­convulsants (Carling et al. 2004), potential inhibitors of serotonin reuptake (Cashman & Ghirmai, 2009), anti-proliferative agents against different human and murine tumor cells (Hall et al., 1992, 2001) and vasorelaxant agents (Nomoto et al. 1990). Therefore, a number of synthetic methods have been developed in recent years to uncover a variety of new reagents for the synthesis of phthalazine derivatives (Mosaddegh & Hassankhani, 2011; Hasaninejed et al., 2012; Keshipour et al., 2012). In previous work, we have reported the synthesis and structure heterocyclic compounds bearing a phthalazine unit (Bouraiou et al., 2015). Herein, we describe the synthesis and crystal structure of the title indazolo phthalazine-trione derivative, resulting from the reaction of phthalhydrazide, cyclo­hexa-1,3-dione and benzaldehyde in the presence of catalytic amounts of sulfuric acid.

The title compound, Fig. 1, consists of an indazolone moiety, bearing a phenyl group, fused to a phthalazine ring system [r.m.s. deviation = 0.018 Å]. The phenyl ring (C16—C21) is almost normal to the mean plane of the five-membered ring (N1/N2/C9/C10/C15) of the indazolone moiety with a dihedral angle of 89.64 (7)°. The six-membered ring of the indazolone moiety (C10—C15) has an envelope conformation with the central methyl­ene C atom, C13, as the flap.

In the crystal, molecules are linked via C—H···O hydrogen bonds forming slabs parallel to the bc plane (Table 1 and Fig. 2). The slabs are linked via C—H···π (Table 1) and slipped parallel π-π inter­actions [the shortest inter-centroid distance involves Cg2···Cg3i = 3.6430 (8) Å; Cg2 and Cg3 are the centroids of rings (N1/N2/C1/C2/C7/C8) and (C2—C7), respectively; inter-planar distance = 3.457 (5); slippage = 1.07 Å; symmetry code: (i) -x+1, -y, -z], forming a three-dimensional structure.

For application of phthalazine derivatives see: Mosaddegh & Hassankhani (2011); Hasaninejed et al. (2012); Keshipour et al. (2012). For the synthesis of this class of compounds, see: Carling et al. (2004); Cashman & Ghirmai (2009); Hall et al. (1992, 2001); Bouraiou et al. (2015); Nomoto et al. (1990). For the synthesis of the title compound, see: Bouraiou et al. (2015); Khurana & Magoo (2009); Nagarapu et al. (2009).

Synthesis and crystallization top

The title compound was synthesized in accordance with established methods (Khurana & Magoo, 2009; Bouraiou et al., 2015). Spectroscopic results and physical properties are in agreement with literature reports (Nagarapu et al., 2009). The solid obtained, was recrystallized in a hot CHCl3/EtOAc/EtOH (1:1:1) mixture giving yellow crystals of the title compound. MS (ES-API): m/z [M+H]+ = 345.1; 1H-NMR δ (ppm) (250 MHz, CDCl3): 8.35–8.23 (m, 2H), 7.88–7.84 (m, 2H), 7.32–7.30 (m, 5H), 6.46 (s, 1H), 3.63–3.30 (m, 2H), 2.51–2.46 (m, 2H), 2.32–2.22 (m, 2H); 13C-NMR δ (ppm) (62.9 MHz, 3): 192.6, 156.1, 154.3, 152.3, 136.4, 134.6, 133.6, 129.1, 129.0, 128.7, 128.0, 127.8, 127.2, 119.7, 65.0, 37.0, 24.6, 22.3.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were located in difference Fourier maps but introduced in calculated positions and refined as riding atoms: C—H = 0.93-0.98 Å with Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecule structure of the title compound, with atom labelling. Displacement are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the a axis of the crystal packing of the title compound, showing the C—H···O hydrogen bonds as dashed lines (see Table 1).
13-Phenyl-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione top
Crystal data top
C21H16N2O3F(000) = 720
Mr = 344.36Dx = 1.362 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4002 reflections
a = 8.9028 (2) Åθ = 3.0–30.5°
b = 11.4507 (3) ŵ = 0.09 mm−1
c = 17.0274 (4) ÅT = 295 K
β = 104.618 (1)°Prism, yellow
V = 1679.64 (7) Å30.13 × 0.09 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		4873 independent reflections
Radiation source: Enraf Nonius FR5903617 reflections with I > 2σ(I)
Graphite monochromatorRint = 0
CCD rotation images, thick slices scansθmax = 30.6°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2011)		h = −12→12
Tmin = 0.957, Tmax = 0.986k = 0→16
4873 measured reflectionsl = 0→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.1115P)2 + 0.0058P]
where P = (Fo2 + 2Fc2)/3
4873 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.6 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C21H16N2O3V = 1679.64 (7) Å3
Mr = 344.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.9028 (2) ŵ = 0.09 mm−1
b = 11.4507 (3) ÅT = 295 K
c = 17.0274 (4) Å0.13 × 0.09 × 0.05 mm
β = 104.618 (1)°
Data collection top
Bruker APEXII
diffractometer		4873 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)		3617 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.986Rint = 0
4873 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.182H-atom parameters constrained
S = 1.12Δρmax = 0.6 e Å−3
4873 reflectionsΔρmin = −0.28 e Å−3
235 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.75069 (15)0.02395 (11)0.00764 (7)0.0373 (3)
C20.68676 (14)−0.05024 (11)0.06179 (7)0.0350 (3)
C30.69309 (16)−0.17117 (12)0.05347 (9)0.0452 (3)
H30.7353−0.20310.01360.054*
C40.63708 (18)−0.24340 (13)0.10405 (10)0.0519 (4)
H40.6422−0.3240.09860.062*
C50.57284 (17)−0.19596 (15)0.16328 (10)0.0525 (4)
H50.5359−0.2450.19770.063*
C60.56360 (16)−0.07659 (14)0.17128 (9)0.0455 (3)
H60.5189−0.04540.21050.055*
C70.62114 (13)−0.00234 (12)0.12069 (7)0.0359 (3)
C80.60888 (14)0.12553 (12)0.12975 (7)0.0369 (3)
C90.66558 (13)0.31891 (11)0.07410 (7)0.0332 (3)
H90.55740.34540.06110.04*
C100.73305 (14)0.33728 (11)0.00262 (7)0.0350 (3)
C110.74291 (16)0.44774 (12)−0.03792 (8)0.0425 (3)
C120.8090 (2)0.43883 (17)−0.11124 (11)0.0664 (5)
H12A0.72420.4281−0.15920.08*
H12B0.85990.5119−0.11750.08*
C130.9230 (3)0.34114 (17)−0.10670 (12)0.0689 (5)
H13A1.01520.358−0.06390.083*
H13B0.95340.3375−0.15750.083*
C140.85967 (17)0.22277 (14)−0.09042 (8)0.0464 (3)
H14A0.78730.1942−0.13920.056*
H14B0.94390.167−0.07470.056*
C150.77933 (14)0.23569 (11)−0.02380 (7)0.0347 (3)
C160.75871 (13)0.37878 (11)0.15078 (7)0.0329 (3)
C170.91360 (15)0.35115 (14)0.18289 (8)0.0455 (3)
H170.95990.29260.15930.055*
C181.00001 (17)0.41101 (16)0.25044 (8)0.0532 (4)
H181.10360.39160.27230.064*
C190.93283 (19)0.49868 (14)0.28486 (8)0.0504 (4)
H190.99170.53980.32910.06*
C200.7781 (2)0.52582 (13)0.25386 (8)0.0510 (4)
H200.73190.58410.27780.061*
C210.69169 (16)0.46548 (12)0.18660 (8)0.0414 (3)
H210.58750.48390.16560.05*
N10.74174 (12)0.14291 (9)0.02082 (6)0.0351 (2)
N20.67235 (12)0.19043 (10)0.07981 (6)0.0355 (2)
O10.80699 (15)−0.01280 (10)−0.04590 (6)0.0574 (3)
O20.54814 (13)0.17285 (10)0.17821 (6)0.0539 (3)
O30.69339 (14)0.53847 (10)−0.01668 (7)0.0591 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0465 (6)0.0302 (6)0.0353 (6)0.0009 (5)0.0105 (5)0.0003 (5)
C20.0378 (6)0.0291 (6)0.0350 (6)−0.0002 (5)0.0031 (4)0.0034 (4)
C30.0509 (7)0.0333 (7)0.0476 (7)0.0004 (6)0.0055 (6)0.0010 (5)
C40.0562 (8)0.0319 (7)0.0630 (9)−0.0035 (6)0.0064 (7)0.0072 (6)
C50.0506 (7)0.0452 (8)0.0599 (9)−0.0093 (7)0.0109 (6)0.0166 (7)
C60.0442 (7)0.0452 (8)0.0483 (7)−0.0045 (6)0.0139 (5)0.0077 (6)
C70.0345 (6)0.0353 (7)0.0359 (6)−0.0030 (5)0.0049 (4)0.0035 (5)
C80.0389 (6)0.0371 (7)0.0362 (6)−0.0031 (5)0.0120 (4)0.0007 (5)
C90.0361 (5)0.0289 (6)0.0347 (6)0.0007 (5)0.0093 (4)−0.0005 (4)
C100.0397 (6)0.0333 (7)0.0314 (5)−0.0019 (5)0.0079 (4)0.0008 (4)
C110.0483 (7)0.0347 (7)0.0437 (7)−0.0015 (6)0.0103 (5)0.0054 (5)
C120.0946 (13)0.0509 (10)0.0660 (10)0.0039 (9)0.0433 (9)0.0181 (8)
C130.0916 (13)0.0537 (11)0.0784 (11)−0.0096 (9)0.0530 (10)0.0009 (9)
C140.0575 (8)0.0435 (8)0.0449 (7)−0.0030 (7)0.0254 (6)−0.0026 (6)
C150.0395 (6)0.0325 (6)0.0325 (6)−0.0035 (5)0.0097 (4)−0.0003 (5)
C160.0388 (6)0.0304 (6)0.0307 (5)−0.0023 (5)0.0110 (4)0.0020 (4)
C170.0405 (6)0.0532 (9)0.0426 (6)0.0032 (6)0.0101 (5)−0.0055 (6)
C180.0423 (7)0.0717 (12)0.0419 (7)−0.0076 (7)0.0037 (5)0.0002 (7)
C190.0636 (9)0.0497 (8)0.0348 (6)−0.0164 (7)0.0068 (6)−0.0031 (6)
C200.0734 (10)0.0380 (7)0.0417 (7)0.0005 (7)0.0145 (6)−0.0052 (6)
C210.0491 (7)0.0354 (7)0.0399 (6)0.0057 (6)0.0115 (5)0.0002 (5)
N10.0445 (5)0.0300 (5)0.0341 (5)−0.0001 (4)0.0159 (4)−0.0015 (4)
N20.0449 (5)0.0295 (5)0.0362 (5)−0.0021 (4)0.0178 (4)−0.0020 (4)
O10.0895 (8)0.0395 (6)0.0544 (6)0.0026 (6)0.0389 (6)−0.0047 (5)
O20.0670 (7)0.0471 (7)0.0603 (6)−0.0031 (5)0.0394 (5)−0.0030 (5)
O30.0773 (8)0.0356 (6)0.0685 (7)0.0087 (5)0.0262 (6)0.0081 (5)
Geometric parameters (Å, º) top
C1—O11.2206 (16)C11—C121.512 (2)
C1—N11.3861 (16)C12—C131.499 (3)
C1—C21.4700 (18)C12—H12A0.97
C2—C71.3942 (19)C12—H12B0.97
C2—C31.3945 (19)C13—C141.520 (2)
C3—C41.375 (2)C13—H13A0.97
C3—H30.93C13—H13B0.97
C4—C51.389 (3)C14—C151.4932 (19)
C4—H40.93C14—H14A0.97
C5—C61.378 (2)C14—H14B0.97
C5—H50.93C15—N11.3951 (16)
C6—C71.3964 (18)C16—C211.3775 (18)
C6—H60.93C16—C171.3857 (18)
C7—C81.4793 (19)C17—C181.3921 (19)
C8—O21.2215 (16)C17—H170.93
C8—N21.3554 (16)C18—C191.373 (2)
C9—N21.4746 (17)C18—H180.93
C9—C101.5019 (17)C19—C201.381 (2)
C9—C161.5217 (16)C19—H190.93
C9—H90.98C20—C211.3915 (19)
C10—C151.3487 (18)C20—H200.93
C10—C111.4541 (18)C21—H210.93
C11—O31.2187 (18)N1—N21.4142 (14)
O1—C1—N1120.73 (12)H12A—C12—H12B107.6
O1—C1—C2124.48 (13)C12—C13—C14113.43 (16)
N1—C1—C2114.78 (11)C12—C13—H13A108.9
C7—C2—C3119.92 (13)C14—C13—H13A108.9
C7—C2—C1121.51 (12)C12—C13—H13B108.9
C3—C2—C1118.57 (13)C14—C13—H13B108.9
C4—C3—C2120.21 (15)H13A—C13—H13B107.7
C4—C3—H3119.9C15—C14—C13108.72 (12)
C2—C3—H3119.9C15—C14—H14A109.9
C3—C4—C5120.01 (15)C13—C14—H14A109.9
C3—C4—H4120C15—C14—H14B109.9
C5—C4—H4120C13—C14—H14B109.9
C6—C5—C4120.36 (14)H14A—C14—H14B108.3
C6—C5—H5119.8C10—C15—N1109.86 (11)
C4—C5—H5119.8C10—C15—C14125.73 (12)
C5—C6—C7120.17 (15)N1—C15—C14124.41 (12)
C5—C6—H6119.9C21—C16—C17119.28 (12)
C7—C6—H6119.9C21—C16—C9120.10 (11)
C2—C7—C6119.32 (13)C17—C16—C9120.54 (11)
C2—C7—C8121.32 (11)C16—C17—C18120.07 (14)
C6—C7—C8119.35 (12)C16—C17—H17120
O2—C8—N2120.42 (13)C18—C17—H17120
O2—C8—C7124.50 (12)C19—C18—C17120.21 (13)
N2—C8—C7115.08 (11)C19—C18—H18119.9
N2—C9—C10100.09 (10)C17—C18—H18119.9
N2—C9—C16112.86 (9)C18—C19—C20120.09 (13)
C10—C9—C16112.92 (10)C18—C19—H19120
N2—C9—H9110.2C20—C19—H19120
C10—C9—H9110.2C19—C20—C21119.60 (14)
C16—C9—H9110.2C19—C20—H20120.2
C15—C10—C11122.13 (12)C21—C20—H20120.2
C15—C10—C9111.58 (11)C16—C21—C20120.74 (13)
C11—C10—C9126.22 (12)C16—C21—H21119.6
O3—C11—C10122.07 (13)C20—C21—H21119.6
O3—C11—C12123.22 (13)C1—N1—C15128.95 (11)
C10—C11—C12114.58 (13)C1—N1—N2123.12 (11)
C13—C12—C11114.02 (14)C15—N1—N2107.56 (10)
C13—C12—H12A108.7C8—N2—N1124.10 (11)
C11—C12—H12A108.7C8—N2—C9124.87 (11)
C13—C12—H12B108.7N1—N2—C9110.79 (9)
C11—C12—H12B108.7
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.932.593.488 (2)163
C9—H9···O3ii0.982.543.501 (2)165
C18—H18···Cg3iii0.932.683.552 (2)156
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.932.593.488 (2)163
C9—H9···O3ii0.982.543.501 (2)165
C18—H18···Cg3iii0.932.683.552 (2)156
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+2, y+1/2, −z+1/2.
 

Acknowledgements

Thanks are due to MESRS and DG–RSDT (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et la Direction Générale de la Recherche – Algérie) for financial support.

References

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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o1036-o1037
https://doi.org/10.1107/S2056989015023452
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