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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 66| Part 9| September 2010| Pages o2304-o2305
https://doi.org/10.1107/S1600536810031582

N-Iso­propyl-6-methyl-2-phenyl­quinoline-3-carboxamide

Saida Benzerka,a Abdelmalek Bouraiou,a Sofiane Bouacida,b* Thierry Roisnelc and Ali Belfaitaha

aLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria, bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria, and cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 27 July 2010; accepted 5 August 2010; online 18 August 2010)

In the title compound, C20H20N2O, the dihedral angle between the quinoline ring system and the phenyl ring is 49.40 (5)°. In the crystal structure, zigzag layers of mol­ecules, in which the quinoline units are parallel to the ([\overline{1}]10) plane, are arranged perpendicular to the b axis. Inter­molecular N—H⋯O hydrogen bonds connect the mol­ecules into chains along [010], reinforcing the cohesion between the layers of the structure.

Related literature

For our previous work on the preparation of quinoline deriv­atives, see: Benzerka et al. (2008[Benzerka, S., Bouraiou, A., Bouacida, S., Rhouati, S. & Belfaitah, A. (2008). Acta Cryst. E64, o2089-o2090.]); Ladraa et al. (2009[Ladraa, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2009). Acta Cryst. C65, o475-o478.]); Bouraiou et al. (2006[Bouraiou, A., Menasra, H., Debache, A., Rhouati, S. & Belfaitah, A. (2006). J. Soc. Alger. Chim. 16, 171-183.], 2008[Bouraiou, A., Debache, A., Rhouati, S., Carboni, B. & Belfaitah, A. (2008). J. Heterocycl. Chem. 45, 329-333.]). For the evaluation of their biological activity, see: Atwell et al. (1988[Atwell, G. J., Bos, C. D., Baguley, B. C. & Denny, W. A. (1988). J. Med. Chem. 31, 1048-1052.],1989[Atwell, G. J., Baguley, B. C. & Denny, W. A. (1989). J. Med. Chem. 32, 396-401.]); Denny et al. (1990[Denny, W. A. G. W., Rewcastle, G. W. B. C. & Baguley, B. C. (1990). J. Med. Chem. 33, 814-819.]); Toshima et al. (1999[Toshima, K., Takano, R., Maeda, Y., Suzuki, M., Asai, A. & Matsumura, S. (1999). Angew. Chem. Int. Ed. 38, 3733-3735.]); Mikata et al. (1998[Mikata, Y., Yokoyama, M., Ogura, S., Okura, I., Kawasaki, M., Maeda, M. & Yano, S. (1998). Bioorg. Med. Chem. Lett. 8, 1243-1248.]); Henriksen et al. (1991[Henriksen, U., Larsen, C., Karup, G., Jeppesen, C., Nielsen, P. E. & Buchardt, O. (1991). Photochem. Photobiol. 53, 299-305.]). For the synthetic procedure, see: Saudi et al. (2003[Saudi, M. N. S., Rostom, S. A. F., Fahmy, H. T. Y. & El Ashmawy, I. M. (2003). Arch. Pharm. Pharm. Med. Chem. 336, 165-174.]).

[Scheme 1]

Experimental

Crystal data

  • C20H20N2O

  • Mr = 304.38

  • Orthorhombic, P b c a

  • a = 12.0007 (3) Å

  • b = 9.6314 (2) Å

  • c = 29.4627 (8) Å

  • V = 3405.40 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 150 K

  • 0.32 × 0.11 × 0.08 mm
Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.747, Tmax = 0.994

  • 15315 measured reflections

  • 3906 independent reflections

  • 2839 reflections with I > 2σ(I)

  • Rint = 0.046
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.157

  • S = 1.04

  • 3906 reflections

  • 211 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N⋯O1i 0.88 1.95 2.804 (3) 164
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003[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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031582/lh5101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031582/lh5101Isup2.hkl

checkCIF report


Comment top

Since Atwell et al. (1988) and Denny et al. (1990) demonstrated the efficacy of 2 + 1 unfused tricyclic aromatic systems such as phenylquinolines as a minimal intercalators, 2-phenylquinoline (Mikata et al., 1998; Henriksen et al., 1991) was selected as the DNA intercalator. The conjugated C=N bond in the 2-phenylquinoline unit was also expected to generate the photoexcited 3(n→π*) state upon photoirradiation, which may have a radical character and could be capable of cleaving DNA (Toshima et al., 1999). On the other hand, certain 2-phenylquinoline carboxamide derivatives have been shown to possess DNA binding capability and a broad-spectrum activity in both leukemia and solid-tumor assays (Atwell et al., 1989). As part of our program related to the synthesis of some new heterocyclic compounds with medicinal potential (Bouraiou et al.,2006, 2008; Benzerka et al., 2008; Ladraa et al., 2009), we report here the synthesis and crystal structure of the title compound (I). The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of title compound contains a quinolyl unit bearing a phenyl ring at position C-2, amide group at C-3 and methyl at C-6. The two rings of the quinolyl moiety are fused in an axial fashion and form a dihedral angle of 3.13 (4)°. The dihedral angle between the phenyl ring quinoline ring system is 49.40 (5)°. The amide group is essentially planar. The r.m.s deviation for atoms C2/C17/O1/N2/C18 is 0.007Å and the maximum deviation is -0.0131 (15)Å for C17. The C—N [1.3260 (17) Å] bond length to the carbonyl group is closer to that of a standard C═N double bond (1.27 Å) than to that of a single bond (1.49 Å). This is because the lone pair electrons on nitrogen of the amide are delocalized into the carbonyl group. The crystal packing can be described as layers in zig zag perpendicular to b axis which quinoline rings are parallel to the (-110) plane (Fig. 2). The crystal packing is stabilized by intermolecular hydrogen bond (N—H···O), resulting in the formation of infinite one-dimensional chain along the b axis linked these layers reinforce the cohesion of the structure (Fig. 2).

Related literature top

For our previous work on the preparation of quinoline derivatives, see: Benzerka et al. (2008); Ladraa et al. (2009); Bouraiou et al. (2006, 2008). For the evaluation of their biological activity, see: Atwell et al. (1988,1989); Denny et al. (1990); Toshima et al. (1999); Mikata et al. (1998); Henriksen et al. (1991). For the synthetic procedure, see: Saudi et al. (2003).

Experimental top

Compound (I) was obtained from 6-methyl-2-phenylquinoline-3-carboxylic acid and ethyl chloroformate in presence triethylamine in chloroform (Saudi et al., 2003). Suitable crystals for X-ray diffraction were obtained by slow evaporation of a solution of (I) in diisopropylether at room temperature.

Refinement top

All H atoms were located from Fourier maps but introduced in calculated positions and treated as riding on their parent C atom with C-H = 0.93-0.98Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Structure description top

Since Atwell et al. (1988) and Denny et al. (1990) demonstrated the efficacy of 2 + 1 unfused tricyclic aromatic systems such as phenylquinolines as a minimal intercalators, 2-phenylquinoline (Mikata et al., 1998; Henriksen et al., 1991) was selected as the DNA intercalator. The conjugated C=N bond in the 2-phenylquinoline unit was also expected to generate the photoexcited 3(n→π*) state upon photoirradiation, which may have a radical character and could be capable of cleaving DNA (Toshima et al., 1999). On the other hand, certain 2-phenylquinoline carboxamide derivatives have been shown to possess DNA binding capability and a broad-spectrum activity in both leukemia and solid-tumor assays (Atwell et al., 1989). As part of our program related to the synthesis of some new heterocyclic compounds with medicinal potential (Bouraiou et al.,2006, 2008; Benzerka et al., 2008; Ladraa et al., 2009), we report here the synthesis and crystal structure of the title compound (I). The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of title compound contains a quinolyl unit bearing a phenyl ring at position C-2, amide group at C-3 and methyl at C-6. The two rings of the quinolyl moiety are fused in an axial fashion and form a dihedral angle of 3.13 (4)°. The dihedral angle between the phenyl ring quinoline ring system is 49.40 (5)°. The amide group is essentially planar. The r.m.s deviation for atoms C2/C17/O1/N2/C18 is 0.007Å and the maximum deviation is -0.0131 (15)Å for C17. The C—N [1.3260 (17) Å] bond length to the carbonyl group is closer to that of a standard C═N double bond (1.27 Å) than to that of a single bond (1.49 Å). This is because the lone pair electrons on nitrogen of the amide are delocalized into the carbonyl group. The crystal packing can be described as layers in zig zag perpendicular to b axis which quinoline rings are parallel to the (-110) plane (Fig. 2). The crystal packing is stabilized by intermolecular hydrogen bond (N—H···O), resulting in the formation of infinite one-dimensional chain along the b axis linked these layers reinforce the cohesion of the structure (Fig. 2).

For our previous work on the preparation of quinoline derivatives, see: Benzerka et al. (2008); Ladraa et al. (2009); Bouraiou et al. (2006, 2008). For the evaluation of their biological activity, see: Atwell et al. (1988,1989); Denny et al. (1990); Toshima et al. (1999); Mikata et al. (1998); Henriksen et al. (1991). For the synthetic procedure, see: Saudi et al. (2003).

Computing details top

Data collection: APEX2 (Bruker,2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure (Farrugia, 1997) of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal structure (Brandenburg & Berndt, 2001) showing the layered packing of (I) viewed along the c axis and showing hydrogen bonds [N—H···O] as dashed line along the b axis.
N-Isopropyl-6-methyl-2-phenylquinoline-3-carboxamide top
Crystal data top
C20H20N2OF(000) = 1296
Mr = 304.38Dx = 1.187 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4726 reflections
a = 12.0007 (3) Åθ = 3.0–27.3°
b = 9.6314 (2) ŵ = 0.07 mm−1
c = 29.4627 (8) ÅT = 150 K
V = 3405.40 (14) Å3Stick, colourless
Z = 80.32 × 0.11 × 0.08 mm
Data collection top
Bruker APEXII
diffractometer		2839 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −10→15
Tmin = 0.747, Tmax = 0.994k = −7→12
15315 measured reflectionsl = −24→38
3906 independent reflections
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0914P)2 + 0.3352P]
where P = (Fo2 + 2Fc2)/3
3906 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C20H20N2OV = 3405.40 (14) Å3
Mr = 304.38Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.0007 (3) ŵ = 0.07 mm−1
b = 9.6314 (2) ÅT = 150 K
c = 29.4627 (8) Å0.32 × 0.11 × 0.08 mm
Data collection top
Bruker APEXII
diffractometer		3906 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2839 reflections with I > 2σ(I)
Tmin = 0.747, Tmax = 0.994Rint = 0.046
15315 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.04Δρmax = 0.23 e Å−3
3906 reflectionsΔρmin = −0.26 e Å−3
211 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.29293 (9)−0.22115 (10)0.10660 (4)0.0378 (3)
N10.58409 (10)−0.43666 (12)0.14988 (4)0.0288 (3)
N20.21063 (10)−0.43091 (12)0.09977 (4)0.0309 (3)
H2N0.2211−0.52130.09840.037*
C10.47981 (11)−0.39345 (14)0.14808 (5)0.0258 (3)
C20.40933 (11)−0.41975 (13)0.10973 (5)0.0240 (3)
C30.44903 (12)−0.50023 (13)0.07517 (5)0.0249 (3)
H30.4038−0.52010.05040.030*
C40.55847 (12)−0.55334 (13)0.07693 (4)0.0251 (3)
C50.60463 (12)−0.64177 (14)0.04333 (5)0.0289 (3)
H50.5619−0.66540.01820.035*
C60.71088 (13)−0.69338 (15)0.04705 (5)0.0335 (4)
C70.77548 (13)−0.65292 (17)0.08495 (6)0.0352 (4)
H70.8477−0.68700.08780.042*
C80.73505 (13)−0.56529 (16)0.11750 (5)0.0332 (4)
H80.7805−0.53840.14150.040*
C90.62453 (11)−0.51521 (14)0.11490 (5)0.0266 (3)
C100.75887 (16)−0.79114 (18)0.01255 (6)0.0448 (4)
H10A0.7119−0.7928−0.01380.067*
H10B0.7633−0.88270.02530.067*
H10C0.8321−0.76040.00410.067*
C110.43566 (13)−0.32106 (16)0.18883 (5)0.0328 (4)
C120.33582 (14)−0.3632 (2)0.20819 (6)0.0464 (5)
H120.2956−0.43520.19500.056*
C130.29535 (17)−0.2991 (3)0.24697 (7)0.0681 (7)
H130.2292−0.32910.26020.082*
C140.3541 (2)−0.1903 (3)0.26577 (8)0.0792 (8)
H140.3264−0.14520.29130.095*
C150.4537 (2)−0.1480 (2)0.24698 (7)0.0690 (7)
H150.4928−0.07460.25990.083*
C160.49557 (16)−0.21433 (18)0.20900 (6)0.0454 (4)
H160.5639−0.18740.19700.055*
C170.29824 (12)−0.34913 (13)0.10575 (5)0.0258 (3)
C180.09700 (12)−0.37692 (16)0.09527 (6)0.0395 (4)
H180.1017−0.28520.08100.047*
C190.03298 (16)−0.4717 (2)0.06337 (11)0.0859 (9)
H19A0.0293−0.56330.07620.129*
H19B0.0703−0.47550.03460.129*
H19C−0.0411−0.43630.05920.129*
C200.04341 (19)−0.3592 (3)0.14068 (8)0.0850 (9)
H20A0.0880−0.29830.15900.128*
H20B0.0374−0.44790.15530.128*
H20C−0.0296−0.32010.13690.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0403 (7)0.0158 (5)0.0574 (7)−0.0006 (4)−0.0080 (5)0.0015 (4)
N10.0269 (6)0.0314 (6)0.0281 (6)−0.0029 (5)0.0000 (5)0.0012 (5)
N20.0234 (6)0.0155 (5)0.0539 (8)0.0019 (5)−0.0045 (6)0.0033 (5)
C10.0264 (7)0.0220 (6)0.0290 (7)−0.0029 (5)−0.0008 (6)0.0020 (5)
C20.0241 (7)0.0167 (6)0.0312 (7)−0.0031 (5)−0.0019 (6)0.0030 (5)
C30.0287 (7)0.0185 (6)0.0276 (7)−0.0038 (5)−0.0045 (6)0.0018 (5)
C40.0285 (7)0.0194 (6)0.0276 (7)−0.0035 (6)0.0024 (6)0.0046 (5)
C50.0338 (8)0.0236 (7)0.0293 (7)−0.0017 (6)0.0025 (6)0.0039 (6)
C60.0369 (9)0.0269 (7)0.0367 (8)0.0015 (6)0.0116 (7)0.0071 (6)
C70.0260 (8)0.0376 (8)0.0421 (9)0.0049 (6)0.0069 (7)0.0106 (7)
C80.0260 (8)0.0407 (9)0.0328 (8)−0.0018 (6)−0.0001 (6)0.0064 (6)
C90.0260 (7)0.0254 (7)0.0283 (7)−0.0030 (6)0.0024 (6)0.0066 (6)
C100.0501 (10)0.0400 (9)0.0444 (10)0.0111 (8)0.0159 (8)0.0012 (8)
C110.0324 (8)0.0356 (8)0.0304 (8)0.0071 (7)−0.0068 (6)−0.0031 (6)
C120.0364 (10)0.0642 (12)0.0387 (10)0.0050 (8)0.0019 (7)−0.0107 (8)
C130.0471 (12)0.112 (2)0.0449 (11)0.0199 (12)0.0061 (9)−0.0181 (12)
C140.0741 (16)0.115 (2)0.0487 (13)0.0337 (15)−0.0048 (12)−0.0389 (13)
C150.0828 (17)0.0685 (14)0.0557 (13)0.0135 (12)−0.0237 (12)−0.0327 (11)
C160.0486 (10)0.0439 (10)0.0437 (10)0.0031 (8)−0.0122 (8)−0.0103 (8)
C170.0289 (8)0.0179 (6)0.0307 (7)0.0003 (5)−0.0024 (6)0.0015 (5)
C180.0243 (8)0.0248 (7)0.0695 (11)0.0047 (6)−0.0029 (8)0.0120 (7)
C190.0369 (11)0.0361 (10)0.185 (3)0.0037 (8)−0.0494 (14)−0.0047 (14)
C200.0510 (13)0.112 (2)0.0926 (18)0.0396 (13)0.0298 (12)0.0511 (16)
Geometric parameters (Å, º) top
O1—C171.2346 (16)C10—H10B0.9600
N1—C11.3198 (18)C10—H10C0.9600
N1—C91.3676 (18)C11—C121.388 (2)
N2—C171.3255 (18)C11—C161.388 (2)
N2—C181.4654 (18)C12—C131.387 (3)
N2—H2N0.8800C12—H120.9300
C1—C21.4339 (19)C13—C141.379 (4)
C1—C111.486 (2)C13—H130.9300
C2—C31.3656 (19)C14—C151.378 (4)
C2—C171.5012 (19)C14—H140.9300
C3—C41.4104 (19)C15—C161.383 (3)
C3—H30.9300C15—H150.9300
C4—C51.4187 (19)C16—H160.9300
C4—C91.419 (2)C18—C201.494 (3)
C5—C61.373 (2)C18—C191.519 (3)
C5—H50.9300C18—H180.9800
C6—C71.414 (2)C19—H19A0.9600
C6—C101.501 (2)C19—H19B0.9600
C7—C81.366 (2)C19—H19C0.9600
C7—H70.9300C20—H20A0.9600
C8—C91.413 (2)C20—H20B0.9600
C8—H80.9300C20—H20C0.9600
C10—H10A0.9600
C1—N1—C9118.72 (12)C12—C11—C1120.19 (14)
C17—N2—C18122.63 (11)C16—C11—C1120.57 (15)
C17—N2—H2N118.7C13—C12—C11120.73 (19)
C18—N2—H2N118.7C13—C12—H12119.6
N1—C1—C2122.37 (13)C11—C12—H12119.6
N1—C1—C11116.96 (12)C14—C13—C12119.3 (2)
C2—C1—C11120.61 (12)C14—C13—H13120.3
C3—C2—C1118.81 (13)C12—C13—H13120.3
C3—C2—C17120.58 (12)C13—C14—C15120.4 (2)
C1—C2—C17120.36 (12)C13—C14—H14119.8
C2—C3—C4120.22 (13)C15—C14—H14119.8
C2—C3—H3119.9C14—C15—C16120.2 (2)
C4—C3—H3119.9C14—C15—H15119.9
C3—C4—C5123.75 (13)C16—C15—H15119.9
C3—C4—C9117.09 (12)C15—C16—C11120.01 (19)
C5—C4—C9119.16 (13)C15—C16—H16120.0
C6—C5—C4121.61 (13)C11—C16—H16120.0
C6—C5—H5119.2O1—C17—N2123.72 (13)
C4—C5—H5119.2O1—C17—C2119.78 (12)
C5—C6—C7118.20 (14)N2—C17—C2116.46 (11)
C5—C6—C10121.96 (15)N2—C18—C20111.09 (14)
C7—C6—C10119.83 (15)N2—C18—C19108.26 (13)
C8—C7—C6121.98 (14)C20—C18—C19113.9 (2)
C8—C7—H7119.0N2—C18—H18107.8
C6—C7—H7119.0C20—C18—H18107.8
C7—C8—C9120.40 (14)C19—C18—H18107.8
C7—C8—H8119.8C18—C19—H19A109.5
C9—C8—H8119.8C18—C19—H19B109.5
N1—C9—C8118.75 (13)H19A—C19—H19B109.5
N1—C9—C4122.61 (13)C18—C19—H19C109.5
C8—C9—C4118.59 (13)H19A—C19—H19C109.5
C6—C10—H10A109.5H19B—C19—H19C109.5
C6—C10—H10B109.5C18—C20—H20A109.5
H10A—C10—H10B109.5C18—C20—H20B109.5
C6—C10—H10C109.5H20A—C20—H20B109.5
H10A—C10—H10C109.5C18—C20—H20C109.5
H10B—C10—H10C109.5H20A—C20—H20C109.5
C12—C11—C16119.20 (16)H20B—C20—H20C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1i0.881.952.804 (3)164
Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formulaC20H20N2O
Mr304.38
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)12.0007 (3), 9.6314 (2), 29.4627 (8)
V (Å3)3405.40 (14)
Z8
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.32 × 0.11 × 0.08
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.747, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		15315, 3906, 2839
Rint0.046
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.157, 1.04
No. of reflections3906
No. of parameters211
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.26

Computer programs: APEX2 (Bruker,2001), SAINT (Bruker, 2001), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1i0.88001.95002.804 (3)164.00
Symmetry code: (i) −x+1/2, y−1/2, z.
 

Acknowledgements

We are grateful to all personel of the PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance.

References

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Pages o2304-o2305
https://doi.org/10.1107/S1600536810031582
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