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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-[4-(4-Chloro­phen­yl)piperazin-1-yl]-3-(6-oxo-3,4-di­phenyl-1,6-di­hydro­pyridazin-1-yl)propan-1-one

aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey, and dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: aaydin@kastamonu.edu.tr

(Received 26 July 2012; accepted 10 August 2012; online 15 August 2012)

In the title compound, C29H27ClN4O2, the six-membered ring of the pyridazine group is nearly planar [maximum deviation = −0.062 (2) Å] and its mean plane makes dihedral angles of 43.05 (9), 44.71 (10) and 72.57 (9)°, respectively, with the two phenyl and benzene rings. The piperazine ring has a chair conformation and its mean plane is almost perpendicular to the attached benzene ring, with a dihedral angle of 83.20 (16)°. In the crystal, mol­ecules are linked via two pairs of C—H⋯O inter­actions, which result in the formation of chains propagating along [10-1]. Neighbouring chains are linked via C—H⋯π inter­actions.

Related literature

For the synthesis and biological activity of the title compound, see; Doğruer et al. (2007[Doğruer, D. S., Ünlü, S., Küpeli, E., Banoglu, E. & Sahin, M. F. (2007). Turk. J. Pharm. Sci. 4, 57-70.]). For related structures, see: Aydın et al. (2008[Aydın, A., Doğruer, D. S., Akkurt, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o1030.]); Girisha et al. (2008[Girisha, H. R., Naveen, S., Vinaya, K., Sridhar, M. A., Shashidhara Prasad, J. & Rangappa, K. S. (2008). Acta Cryst. E64, o358.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C29H27ClN4O2

  • Mr = 499.00

  • Triclinic, [P \overline 1]

  • a = 10.7929 (10) Å

  • b = 10.8527 (10) Å

  • c = 12.7815 (13) Å

  • α = 97.745 (8)°

  • β = 104.041 (7)°

  • γ = 115.635 (7)°

  • V = 1259.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 296 K

  • 0.66 × 0.53 × 0.35 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.784, Tmax = 0.948

  • 15922 measured reflections

  • 4945 independent reflections

  • 3837 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.111

  • S = 1.05

  • 4945 reflections

  • 326 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the N1/N2/C1–C4 and C11–C16 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯O1i 0.93 2.44 3.323 (2) 158
C25—H25⋯O2ii 0.93 2.53 3.289 (3) 139
C10—H10⋯Cg1iii 0.93 2.88 3.431 (2) 119
C29—H29⋯Cg4iv 0.93 2.86 3.762 (2) 165
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+2; (iv) x, y, z-1.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

1-[4-(4-Chlorophenyl)piperazin-1-yl]-3-(6-oxo-3,4-diphenyl-1,6-dihydropyridazin-1-yl)propan-1-one has analgesic and anti-inflammatory effect. Its in vivo analgesic and anti-inflammatory activities were tested in mice. This compound showed higher analgesic activity than aspirin at 100 mg/kg. Analgesic activity results of the compound also shows good correlation with its anti-inflammatory activity and produced anti-inflammatory activity in both phases of carrageenan-induced edema (Doğruer et al., 2007).

In the present study, the title compound has been synthesized for first time by (Doğruer et al., 2007) and characterized by spectroscopic techniques. Herein we report on the synthesis and its crystal structure.

In the title compound, Fig. 1, the six-membered ring of the pyridazin-3(2H)-one system is nearly planar with maximum deviations of -0.062 (2) Å for N1, 0.052 (2) Å for C1 and -0.045 (2) Å for C3 from the mean plane. The dihedral angles between the mean plane of the six-membered ring (N1/N2/C1–C4) and the phenyl rings C11—C16 and C5—C10 are 44.71 (10)° and 43.05 (9)°, respectively.

As seen in Fig. 1, the Cl1—C27—C28—C29 and N3—C20—C21—N4 torsion angles are 178.69 (14) and 57.22 (18)°, respectively. The double-bond length for C19—O2 is 1.2192 (19) Å and the C27—Cl1 bond length is 1.7450 (19) Å. All bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for similar structures (Aydın et al., 2008; Girisha et al., 2008).

The piperazine ring (N3/N4/C20–C23) has a chair conformation with puckering parameters: QT = 0.566 (2) Å, θ = 0.5 (2) ° and ϕ = 67 (10) ° (Cremer & Pople, 1975). The mean plane of the six-membered ring forms a dihedral angle of 83.20 (16)° with the benzene ring (C24–C29). The phenyl rings (C11–C16) and (C5—C10) make dihedral angles of 67.84 (10)° and 32.76 (9)° with the benzene ring (C24–C29), respectively, whilst the dihedral angle between them is 60.42 (10)°.

In the crystal, molecules are linked via two pairs of C—H···O interactions which result in the formation of chains propagating along [1 0 -1], (Table 1 and Fig. 2). Neighbouring chains are linked via C—H···π interactions (Table 1).

Related literature top

For the synthesis and biological activity of the title compound, see; Doğruer et al. (2007). For related structures, see: Aydın et al. (2008); Girisha et al. (2008). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized according to the literature procedure (Doğruer et al., 2007). 0.01 Mol of compound 3-[5,6-Diphenyl-3(2H)-pyridazinone-2-yl] propanoic acid in 40 ml dichloromethane at 273 K (ice-bath) was treated with triethylamine (1 ml) and 0.01 mol of ethyl chloroformate. After stirring the reaction mixture at 273 K for 15 min, 0.011 mole of 4-chlorophenylpiperazine was added to this solution. This mixture was stirred at 273–298 K for 24 h and evaporated to dryness. The product was then solidified with ice-cold water and recrystallized from ethanol (yield 52%, M.p. 432 K). IR v cm-1 (KBr): 1652 (CO ring, amide).

Refinement top

All the H atoms were positioned geometrically and refined using a riding model: C—H = 0.93 and 0.97 Å for CH and CH2 H atoms, respectively, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
The molecular structure of the title molecule, with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.

A view along the a axis of the crystal packing of the title compound. The C-H···O interactions are shown as dashed lines [see Table 1 for details; H atoms not participating in these interactions have been omitted for clarity].
1-[4-(4-Chlorophenyl)piperazin-1-yl]-3-(6-oxo-3,4-diphenyl-1,6- dihydropyridazin-1-yl)propan-1-one top
Crystal data top
C29H27ClN4O2Z = 2
Mr = 499.00F(000) = 524
Triclinic, P1Dx = 1.316 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7929 (10) ÅCell parameters from 24474 reflections
b = 10.8527 (10) Åθ = 2.2–27.9°
c = 12.7815 (13) ŵ = 0.19 mm1
α = 97.745 (8)°T = 296 K
β = 104.041 (7)°Prism, colourless
γ = 115.635 (7)°0.66 × 0.53 × 0.35 mm
V = 1259.3 (2) Å3
Data collection top
Stoe IPDS 2
diffractometer
4945 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3837 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.059
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = 1313
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1313
Tmin = 0.784, Tmax = 0.948l = 1515
15922 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.165P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4945 reflectionsΔρmax = 0.29 e Å3
326 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (2)
Crystal data top
C29H27ClN4O2γ = 115.635 (7)°
Mr = 499.00V = 1259.3 (2) Å3
Triclinic, P1Z = 2
a = 10.7929 (10) ÅMo Kα radiation
b = 10.8527 (10) ŵ = 0.19 mm1
c = 12.7815 (13) ÅT = 296 K
α = 97.745 (8)°0.66 × 0.53 × 0.35 mm
β = 104.041 (7)°
Data collection top
Stoe IPDS 2
diffractometer
4945 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
3837 reflections with I > 2σ(I)
Tmin = 0.784, Tmax = 0.948Rint = 0.059
15922 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.05Δρmax = 0.29 e Å3
4945 reflectionsΔρmin = 0.37 e Å3
326 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl11.08842 (7)1.37656 (7)0.23195 (6)0.0985 (3)
O10.77526 (16)0.94002 (13)0.89191 (12)0.0766 (5)
O20.37402 (15)0.69982 (19)0.55504 (11)0.0806 (6)
N10.63418 (14)0.70263 (13)0.85637 (11)0.0502 (4)
N20.61006 (14)0.57387 (13)0.87067 (10)0.0470 (4)
N30.52244 (15)0.69229 (17)0.46036 (11)0.0588 (5)
N40.68833 (14)0.88867 (16)0.35873 (11)0.0550 (5)
C10.75365 (19)0.83035 (17)0.91999 (14)0.0557 (5)
C20.84157 (19)0.82159 (17)1.01957 (14)0.0560 (5)
C30.81424 (16)0.69621 (16)1.04284 (12)0.0475 (5)
C40.69752 (16)0.56941 (15)0.95936 (12)0.0446 (4)
C50.66902 (16)0.42329 (15)0.96261 (12)0.0445 (4)
C60.7836 (2)0.39377 (19)0.99172 (15)0.0587 (6)
C70.7563 (2)0.2564 (2)0.98782 (17)0.0680 (7)
C80.6157 (2)0.1486 (2)0.95736 (16)0.0695 (7)
C90.5011 (2)0.17680 (18)0.93023 (15)0.0612 (6)
C100.52791 (18)0.31370 (16)0.93212 (13)0.0505 (5)
C110.89780 (17)0.69523 (16)1.15342 (13)0.0493 (5)
C121.04711 (19)0.78512 (19)1.20005 (16)0.0609 (6)
C131.1225 (2)0.7904 (2)1.30592 (18)0.0758 (7)
C141.0503 (3)0.7066 (2)1.36637 (17)0.0793 (8)
C150.9027 (2)0.6189 (2)1.32177 (15)0.0679 (7)
C160.8258 (2)0.61227 (18)1.21591 (14)0.0556 (5)
C170.53089 (18)0.69840 (18)0.75579 (13)0.0533 (5)
C180.58384 (18)0.69042 (19)0.65707 (13)0.0546 (5)
C190.48415 (18)0.69447 (18)0.55362 (14)0.0545 (5)
C200.45077 (19)0.7272 (2)0.36582 (15)0.0644 (6)
C210.54978 (19)0.8760 (2)0.36406 (15)0.0622 (6)
C220.76026 (19)0.8518 (2)0.45262 (14)0.0579 (6)
C230.66045 (19)0.7045 (2)0.45535 (15)0.0601 (6)
C240.78162 (17)1.00788 (18)0.33070 (13)0.0526 (5)
C250.7588 (2)1.1234 (2)0.32311 (16)0.0648 (6)
C260.8519 (2)1.2354 (2)0.29196 (18)0.0739 (7)
C270.9681 (2)1.2340 (2)0.26832 (16)0.0665 (6)
C280.9917 (2)1.1201 (2)0.27347 (16)0.0643 (6)
C290.89932 (19)1.00883 (19)0.30419 (15)0.0592 (6)
H20.920100.904901.069900.0670*
H60.879300.466901.014000.0700*
H70.833500.237001.005900.0820*
H80.597800.056200.955000.0830*
H90.405800.103800.910700.0740*
H100.450200.332200.912700.0610*
H121.096600.842101.159800.0730*
H131.222700.850801.336700.0910*
H141.101800.709701.437400.0950*
H150.853900.563401.363100.0810*
H160.725500.552201.186100.0670*
H17A0.520400.782900.769200.0640*
H17B0.436000.616200.738900.0640*
H18A0.681300.769500.676100.0660*
H18B0.589200.603200.641500.0660*
H20A0.360400.720300.372200.0770*
H20B0.427400.660100.296300.0770*
H21A0.503100.897500.299500.0750*
H21B0.567400.943700.431100.0750*
H22A0.786300.919500.522500.0700*
H22B0.849200.856500.444600.0700*
H23A0.642500.635900.388800.0720*
H23B0.706800.683500.520300.0720*
H250.680001.125400.339100.0780*
H260.835301.312000.287100.0890*
H281.069901.118400.256200.0770*
H290.916000.932000.307300.0710*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0811 (4)0.0793 (4)0.1288 (5)0.0272 (3)0.0379 (4)0.0461 (4)
O10.0907 (10)0.0489 (7)0.0827 (9)0.0260 (7)0.0238 (7)0.0331 (6)
O20.0747 (9)0.1370 (13)0.0629 (8)0.0719 (10)0.0320 (7)0.0370 (8)
N10.0563 (8)0.0463 (7)0.0512 (7)0.0236 (6)0.0212 (6)0.0214 (6)
N20.0524 (7)0.0427 (6)0.0488 (7)0.0214 (6)0.0215 (6)0.0184 (5)
N30.0588 (8)0.0806 (10)0.0523 (8)0.0420 (8)0.0234 (6)0.0261 (7)
N40.0508 (8)0.0698 (9)0.0524 (8)0.0349 (7)0.0176 (6)0.0207 (7)
C10.0640 (10)0.0456 (8)0.0587 (9)0.0226 (8)0.0263 (8)0.0215 (7)
C20.0590 (10)0.0425 (8)0.0540 (9)0.0145 (7)0.0175 (7)0.0141 (7)
C30.0484 (8)0.0461 (8)0.0487 (8)0.0202 (7)0.0213 (7)0.0159 (6)
C40.0464 (8)0.0442 (7)0.0463 (8)0.0202 (7)0.0215 (6)0.0167 (6)
C50.0521 (8)0.0431 (7)0.0421 (7)0.0234 (7)0.0198 (6)0.0147 (6)
C60.0562 (10)0.0582 (10)0.0687 (10)0.0310 (8)0.0251 (8)0.0194 (8)
C70.0813 (13)0.0719 (12)0.0746 (12)0.0530 (11)0.0305 (10)0.0278 (10)
C80.1002 (15)0.0526 (10)0.0695 (11)0.0433 (11)0.0336 (11)0.0268 (9)
C90.0687 (11)0.0464 (9)0.0605 (10)0.0202 (8)0.0213 (8)0.0184 (7)
C100.0539 (9)0.0462 (8)0.0501 (8)0.0224 (7)0.0174 (7)0.0160 (7)
C110.0519 (9)0.0457 (8)0.0483 (8)0.0233 (7)0.0159 (7)0.0099 (6)
C120.0536 (10)0.0559 (10)0.0696 (11)0.0258 (8)0.0190 (8)0.0125 (8)
C130.0593 (11)0.0720 (12)0.0794 (13)0.0338 (10)0.0009 (10)0.0048 (10)
C140.0937 (16)0.0884 (14)0.0572 (11)0.0577 (13)0.0049 (10)0.0136 (10)
C150.0880 (14)0.0730 (12)0.0547 (10)0.0479 (11)0.0235 (9)0.0231 (9)
C160.0602 (10)0.0568 (9)0.0512 (9)0.0284 (8)0.0190 (7)0.0180 (7)
C170.0561 (9)0.0576 (9)0.0544 (9)0.0297 (8)0.0225 (7)0.0250 (7)
C180.0559 (9)0.0624 (10)0.0555 (9)0.0327 (8)0.0225 (7)0.0248 (8)
C190.0556 (9)0.0622 (10)0.0532 (9)0.0328 (8)0.0211 (7)0.0179 (7)
C200.0545 (10)0.0927 (13)0.0500 (9)0.0378 (10)0.0173 (7)0.0246 (9)
C210.0595 (10)0.0881 (13)0.0544 (9)0.0461 (10)0.0196 (8)0.0281 (9)
C220.0567 (10)0.0717 (11)0.0546 (9)0.0396 (9)0.0170 (7)0.0182 (8)
C230.0649 (10)0.0738 (11)0.0610 (10)0.0439 (10)0.0297 (8)0.0249 (9)
C240.0527 (9)0.0586 (9)0.0440 (8)0.0291 (8)0.0111 (7)0.0084 (7)
C250.0676 (11)0.0726 (11)0.0692 (11)0.0439 (10)0.0275 (9)0.0215 (9)
C260.0813 (13)0.0645 (11)0.0876 (14)0.0436 (11)0.0283 (11)0.0267 (10)
C270.0609 (11)0.0609 (10)0.0667 (11)0.0238 (9)0.0152 (9)0.0165 (8)
C280.0529 (10)0.0674 (11)0.0674 (11)0.0273 (9)0.0181 (8)0.0129 (9)
C290.0568 (10)0.0604 (10)0.0636 (10)0.0326 (9)0.0191 (8)0.0136 (8)
Geometric parameters (Å, º) top
Cl1—C271.745 (2)C24—C251.389 (3)
O1—C11.231 (2)C24—C291.388 (3)
O2—C191.219 (3)C25—C261.383 (3)
N1—N21.3532 (19)C26—C271.365 (3)
N1—C11.373 (2)C27—C281.372 (3)
N1—C171.464 (2)C28—C291.372 (3)
N2—C41.309 (2)C2—H20.9300
N3—C191.354 (2)C6—H60.9300
N3—C201.458 (2)C7—H70.9300
N3—C231.455 (3)C8—H80.9300
N4—C211.461 (3)C9—H90.9300
N4—C221.466 (2)C10—H100.9300
N4—C241.410 (2)C12—H120.9300
C1—C21.433 (3)C13—H130.9300
C2—C31.353 (2)C14—H140.9300
C3—C41.439 (2)C15—H150.9300
C3—C111.485 (2)C16—H160.9300
C4—C51.488 (2)C17—H17A0.9700
C5—C61.386 (3)C17—H17B0.9700
C5—C101.381 (3)C18—H18A0.9700
C6—C71.380 (3)C18—H18B0.9700
C7—C81.370 (3)C20—H20A0.9700
C8—C91.375 (3)C20—H20B0.9700
C9—C101.381 (3)C21—H21A0.9700
C11—C121.386 (3)C21—H21B0.9700
C11—C161.394 (3)C22—H22A0.9700
C12—C131.379 (3)C22—H22B0.9700
C13—C141.378 (3)C23—H23A0.9700
C14—C151.367 (4)C23—H23B0.9700
C15—C161.379 (3)C25—H250.9300
C17—C181.513 (3)C26—H260.9300
C18—C191.508 (3)C28—H280.9300
C20—C211.510 (3)C29—H290.9300
C22—C231.504 (3)
Cl1···H7i3.0900H6···C112.7500
O1···C183.252 (2)H6···H6vii2.5200
O1···C12ii3.323 (2)H7···Cl1xi3.0900
O2···C25iii3.289 (3)H7···H12vii2.5800
O1···H17A2.4600H8···O1xiv2.9100
O1···H8iv2.9100H8···C8viii3.0000
O1···H2ii2.8400H8···C9viii3.0200
O1···H12ii2.4400H8···H8viii2.5700
O1···H18A2.7800H8···H9viii2.6000
O2···H17B2.6700H9···C24v2.9900
O2···H20A2.3500H9···H8viii2.6000
O2···H17A2.6100H10···N22.6600
O2···H25iii2.5300H10···C3vi2.9400
N3···N42.830 (2)H10···C4vi2.9400
N4···N32.830 (2)H12···C22.7900
N2···H102.6600H12···H22.3800
N2···H20Bv2.9000H12···O1ii2.4400
N3···H18Bv2.8600H12···C7vii3.1000
C5···C163.178 (2)H12···H7vii2.5800
C6···C113.154 (3)H13···H20Ax2.4700
C6···C163.262 (3)H14···C25ii2.9700
C9···C21v3.595 (3)H16···C42.8800
C9···C24v3.524 (3)H16···C52.8000
C11···C63.154 (3)H16···H17Bvi2.4100
C12···O1ii3.323 (2)H17A···O12.4600
C16···C53.178 (2)H17A···O22.6100
C16···C63.262 (3)H17B···O22.6700
C18···O13.252 (2)H17B···C16vi3.1000
C21···C9v3.595 (3)H17B···H16vi2.4100
C24···C9v3.524 (3)H18A···O12.7800
C25···O2iii3.289 (3)H18A···C12.9300
C1···H18A2.9300H18A···C232.7400
C2···H122.7900H18A···H23B2.2100
C3···H62.8700H18A···C28xiii3.0600
C3···H10vi2.9400H18A···H28xiii2.2800
C4···H162.8800H18B···C232.8800
C4···H10vi2.9400H18B···H23B2.2700
C5···H20Bv3.0900H18B···N3v2.8600
C5···H162.8000H18B···C23v3.0700
C7···H12vii3.1000H20A···O22.3500
C8···H8viii3.0000H20A···C13xv2.9500
C9···H21Av2.9200H20A···H13xv2.4700
C9···H8viii3.0200H20B···H23A2.4800
C11···H29ix2.9200H20B···N2v2.9000
C11···H62.7500H20B···C5v3.0900
C12···H22.7100H21A···C252.6900
C12···H29ix2.9500H21A···H252.2600
C13···H20Ax2.9500H21A···C9v2.9200
C15···H26xi3.0300H21B···C252.9300
C16···H17Bvi3.1000H21B···H22A2.5100
C18···H23B2.4500H21B···H252.4500
C21···H252.5600H22A···H21B2.5100
C22···H292.7800H22B···C292.6000
C23···H18B2.8800H22B···H292.1800
C23···H18Bv3.0700H23A···H20B2.4800
C23···H18A2.7400H23B···C182.4500
C24···H9v2.9900H23B···H18A2.2100
C25···H21A2.6900H23B···H18B2.2700
C25···H21B2.9300H25···C212.5600
C25···H14ii2.9700H25···H21A2.2600
C28···H2xii2.9400H25···H21B2.4500
C28···H18Axiii3.0600H25···O2iii2.5300
C29···H22B2.6000H26···C15i3.0300
H2···C122.7100H28···H18Axiii2.2800
H2···C28ix2.9400H29···C11xii2.9200
H2···H122.3800H29···C12xii2.9500
H2···O1ii2.8400H29···C222.7800
H6···C32.8700H29···H22B2.1800
N2—N1—C1125.35 (15)C7—C6—H6120.00
N2—N1—C17114.86 (13)C6—C7—H7120.00
C1—N1—C17119.35 (14)C8—C7—H7120.00
N1—N2—C4118.26 (13)C7—C8—H8120.00
C19—N3—C20120.13 (18)C9—C8—H8120.00
C19—N3—C23125.31 (16)C8—C9—H9120.00
C20—N3—C23111.42 (15)C10—C9—H9120.00
C21—N4—C22111.60 (15)C5—C10—H10120.00
C21—N4—C24118.29 (16)C9—C10—H10120.00
C22—N4—C24115.21 (16)C11—C12—H12120.00
O1—C1—N1120.49 (17)C13—C12—H12120.00
O1—C1—C2125.55 (17)C12—C13—H13120.00
N1—C1—C2113.92 (15)C14—C13—H13120.00
C1—C2—C3122.23 (16)C13—C14—H14120.00
C2—C3—C4116.98 (15)C15—C14—H14120.00
C2—C3—C11119.65 (15)C14—C15—H15120.00
C4—C3—C11123.27 (14)C16—C15—H15120.00
N2—C4—C3122.15 (14)C11—C16—H16120.00
N2—C4—C5114.01 (13)C15—C16—H16120.00
C3—C4—C5123.79 (14)N1—C17—H17A110.00
C4—C5—C6120.46 (16)N1—C17—H17B110.00
C4—C5—C10120.58 (17)C18—C17—H17A110.00
C6—C5—C10118.90 (16)C18—C17—H17B110.00
C5—C6—C7120.31 (19)H17A—C17—H17B108.00
C6—C7—C8120.2 (2)C17—C18—H18A109.00
C7—C8—C9120.12 (19)C17—C18—H18B109.00
C8—C9—C10119.85 (19)C19—C18—H18A109.00
C5—C10—C9120.63 (19)C19—C18—H18B109.00
C3—C11—C12120.49 (16)H18A—C18—H18B108.00
C3—C11—C16120.48 (17)N3—C20—H20A110.00
C12—C11—C16118.84 (16)N3—C20—H20B110.00
C11—C12—C13120.20 (18)C21—C20—H20A110.00
C12—C13—C14120.4 (2)C21—C20—H20B110.00
C13—C14—C15119.9 (2)H20A—C20—H20B108.00
C14—C15—C16120.38 (19)N4—C21—H21A110.00
C11—C16—C15120.28 (19)N4—C21—H21B110.00
N1—C17—C18110.42 (17)C20—C21—H21A110.00
C17—C18—C19111.72 (17)C20—C21—H21B110.00
O2—C19—N3121.94 (17)H21A—C21—H21B108.00
O2—C19—C18120.78 (17)N4—C22—H22A110.00
N3—C19—C18117.29 (18)N4—C22—H22B110.00
N3—C20—C21109.95 (16)C23—C22—H22A110.00
N4—C21—C20110.00 (17)C23—C22—H22B110.00
N4—C22—C23110.26 (16)H22A—C22—H22B108.00
N3—C23—C22110.62 (18)N3—C23—H23A110.00
N4—C24—C25123.46 (19)N3—C23—H23B110.00
N4—C24—C29119.06 (17)C22—C23—H23A110.00
C25—C24—C29117.41 (18)C22—C23—H23B110.00
C24—C25—C26120.8 (2)H23A—C23—H23B108.00
C25—C26—C27120.3 (2)C24—C25—H25120.00
Cl1—C27—C26120.62 (17)C26—C25—H25120.00
Cl1—C27—C28119.29 (18)C25—C26—H26120.00
C26—C27—C28120.1 (2)C27—C26—H26120.00
C27—C28—C29119.7 (2)C27—C28—H28120.00
C24—C29—C28121.76 (19)C29—C28—H28120.00
C1—C2—H2119.00C24—C29—H29119.00
C3—C2—H2119.00C28—C29—H29119.00
C5—C6—H6120.00
C1—N1—N2—C48.3 (3)C2—C3—C4—N27.7 (3)
C17—N1—N2—C4179.47 (16)N2—C4—C5—C1042.1 (2)
N2—N1—C1—O1170.70 (18)C3—C4—C5—C642.2 (2)
C17—N1—C1—O11.2 (3)C3—C4—C5—C10140.53 (18)
N2—N1—C1—C211.6 (3)N2—C4—C5—C6135.15 (17)
C17—N1—C1—C2176.54 (17)C6—C5—C10—C90.2 (2)
N2—N1—C17—C1888.78 (18)C10—C5—C6—C71.4 (3)
C1—N1—C17—C1884.0 (2)C4—C5—C10—C9177.05 (15)
N1—N2—C4—C32.0 (3)C4—C5—C6—C7175.90 (16)
N1—N2—C4—C5175.41 (15)C5—C6—C7—C81.4 (3)
C20—N3—C19—O213.4 (3)C6—C7—C8—C90.2 (3)
C23—N3—C19—O2171.58 (19)C7—C8—C9—C101.0 (3)
C23—N3—C20—C2158.0 (2)C8—C9—C10—C51.0 (3)
C19—N3—C20—C21103.0 (2)C12—C11—C16—C150.7 (3)
C23—N3—C19—C188.3 (3)C3—C11—C16—C15175.65 (18)
C19—N3—C23—C22102.3 (2)C16—C11—C12—C130.8 (3)
C20—N3—C19—C18166.45 (16)C3—C11—C12—C13175.75 (18)
C20—N3—C23—C2257.50 (19)C11—C12—C13—C140.0 (3)
C24—N4—C21—C20165.70 (14)C12—C13—C14—C150.8 (4)
C21—N4—C22—C2356.4 (2)C13—C14—C15—C160.9 (4)
C22—N4—C21—C2057.14 (19)C14—C15—C16—C110.2 (3)
C24—N4—C22—C23165.05 (16)N1—C17—C18—C19176.70 (14)
C22—N4—C24—C25126.42 (19)C17—C18—C19—N3178.08 (16)
C21—N4—C24—C29167.77 (15)C17—C18—C19—O21.8 (3)
C21—N4—C24—C259.3 (2)N3—C20—C21—N457.2 (2)
C22—N4—C24—C2956.6 (2)N4—C22—C23—N355.78 (19)
N1—C1—C2—C35.0 (3)N4—C24—C25—C26178.06 (17)
O1—C1—C2—C3177.4 (2)C29—C24—C25—C261.0 (3)
C1—C2—C3—C11172.67 (19)N4—C24—C29—C28178.30 (16)
C1—C2—C3—C43.8 (3)C25—C24—C29—C281.1 (3)
C2—C3—C4—C5169.46 (18)C24—C25—C26—C270.1 (3)
C11—C3—C4—C514.2 (3)C25—C26—C27—Cl1178.59 (16)
C4—C3—C11—C12140.70 (19)C25—C26—C27—C281.1 (3)
C4—C3—C11—C1644.4 (3)Cl1—C27—C28—C29178.70 (15)
C11—C3—C4—N2168.63 (18)C26—C27—C28—C291.0 (3)
C2—C3—C11—C1243.0 (3)C27—C28—C29—C240.1 (3)
C2—C3—C11—C16131.8 (2)
Symmetry codes: (i) x, y+1, z1; (ii) x+2, y+2, z+2; (iii) x+1, y+2, z+1; (iv) x, y+1, z; (v) x+1, y+1, z+1; (vi) x+1, y+1, z+2; (vii) x+2, y+1, z+2; (viii) x+1, y, z+2; (ix) x, y, z+1; (x) x+1, y, z+1; (xi) x, y1, z+1; (xii) x, y, z1; (xiii) x+2, y+2, z+1; (xiv) x, y1, z; (xv) x1, y, z1.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg4 are the centroids of the N1/N2/C1–C4 and C11–C16 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12···O1ii0.932.443.323 (2)158
C25—H25···O2iii0.932.533.289 (3)139
C10—H10···Cg1vi0.932.883.431 (2)119
C29—H29···Cg4xii0.932.863.762 (2)165
Symmetry codes: (ii) x+2, y+2, z+2; (iii) x+1, y+2, z+1; (vi) x+1, y+1, z+2; (xii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC29H27ClN4O2
Mr499.00
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.7929 (10), 10.8527 (10), 12.7815 (13)
α, β, γ (°)97.745 (8), 104.041 (7), 115.635 (7)
V3)1259.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.66 × 0.53 × 0.35
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.784, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections
15922, 4945, 3837
Rint0.059
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.111, 1.05
No. of reflections4945
No. of parameters326
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.37

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg4 are the centroids of the N1/N2/C1–C4 and C11–C16 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.443.323 (2)158
C25—H25···O2ii0.932.533.289 (3)139
C10—H10···Cg1iii0.932.883.431 (2)119
C29—H29···Cg4iv0.932.863.762 (2)165
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+2; (iv) x, y, z1.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals
First citationAydın, A., Doğruer, D. S., Akkurt, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o1030.  Web of Science CSD CrossRef IUCr Journals
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationDoğruer, D. S., Ünlü, S., Küpeli, E., Banoglu, E. & Sahin, M. F. (2007). Turk. J. Pharm. Sci. 4, 57–70.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationGirisha, H. R., Naveen, S., Vinaya, K., Sridhar, M. A., Shashidhara Prasad, J. & Rangappa, K. S. (2008). Acta Cryst. E64, o358.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds