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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-[2-(4-Benzyl­piperazin-1-ylcarbon­yl)eth­yl]-5,6-di­phenyl­pyridazin-3(2H)-one

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

(Received 1 May 2008; accepted 4 May 2008; online 10 May 2008)

The title compound, C30H30N4O2, has a non-planar conformation, the dihedral angles formed by the pyridazinone ring plane and the three phenyl rings being 54.61 (7), 51.10 (7) and 59.53 (8)°. The piperazine ring adopts a chair conformation. Inter- and intra­molecular C—H⋯O contacts are found in the crystal structure and these consolidate the three-dimensional packing.

Related literature

For related structures, see: Doğruer et al. (2007[Doğruer, D. S., Ünlü, S., Küpeli, E., Banoğlu, E. & Şahin, M. F. (2007). Turk. J. Pharm. Sci. 4, 57-70.]); Swenson et al. (1997[Swenson, D. C., Yamamoto, M. & Burton, D. J. (1997). Acta Cryst. C53, 1445-1447.]); Yüksektepe et al. (2004[Yüksektepe, Ç., Saraçoğlu, H., Koca, M., Çukurovali, A. & Çalışkan, N. (2004). Acta Cryst. C60, o509-o510.]). For structure analysis, 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.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C30H30N4O2

  • Mr = 478.58

  • Monoclinic, P 21 /c

  • a = 15.6725 (12) Å

  • b = 9.1139 (5) Å

  • c = 17.6743 (12) Å

  • β = 90.553 (6)°

  • V = 2524.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.73 × 0.51 × 0.11 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 = 0.477, Tmax = 0.907

  • 30083 measured reflections

  • 4966 independent reflections

  • 3394 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.094

  • S = 1.03

  • 4966 reflections

  • 325 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O2i 0.93 2.47 3.3470 (19) 157
C18—H18B⋯O1 0.97 2.56 3.0755 (18) 113
C20—H20B⋯O2 0.97 2.35 2.759 (2) 105
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

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

The title compound (I) was prepared recently (Doğruer et al., 2007) and displays analgesic and anti-inflammatory effects. In the crystal structure of (I), Fig. 1, the bond lengths and angles are within their normal ranges (Allen et al., 1987). The piperazine bridge has a normal chair conformation, with puckering parameters (Cremer & Pople, 1975) QT = 0.562 (2) Å, θ = 176.2 (2) ° and ϕ = 354 (3) °. Relevant literature values for the puckering of the cyclobutane ring are 29.0 (1)° (Yüksektepe et al., 2004) and 23.5° (Swenson et al., 1997). In this study, the N1/N2/C1—C4 pyridazinone ring plane forms dihedral angles of 54.61 (7), 51.10 (7) and 59.53 (8)°, respectively, with the planes of the (A: C5—C10), (B: C11—C16) and (C: C25 –C30) phenyl rings. The dihedral angles between the phenyl rings are A/B = 50.77 (8), A/C = 83.01 (9) and B/C = 70.15 (9)°.

The crystal structure is stabilized by inter and intramolecular C—H···O contacts that stabilize the three-dimensional network (Table 1, Fig. 2).

Related literature top

For related structures, see: Doğruer et al. (2007); Swenson et al. (1997); Yüksektepe et al. (2004). For structure analysis, see: Allen et al. (1987); Cremer & Pople (1975).

Experimental top

[3-(5,6-Diphenyl-3(2H)-pyridazinone-2-yl)propanoic acid (0.01 mol) in dichloromethane (40 ml) at 273 K (ice-bath) was treated with triethylamine (1 ml) and ethyl chloroformate (0.01 mol). After stirring the reaction mixture at 273 K for 15 min, benzylpiperazine (0.011 mol) was added. The final mixture was stirred at 273–298 K for 24 h and evaporated to dryness. The product was solidified with ice-cold water and crystallized from ethanol (yield 25%, m.p. 422 K). IR vmax(cm-1) (KBr): 1660 (CO ring), 1635 (CO amide) (Doğruer et al., 2007).

Refinement top

All H atoms were then placed in geometrically idealized positions and constrained to ride on their parent atoms, with Csp3—H = 0.97 Å and Csp2—H = 0.93 Å, and 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
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the hydrogen bonding interactions (dashed lines) in (I) down b axis. H atoms not involved in hydrogen bonding interactions have been omitted for clarity.
2-[2-(4-Benzylpiperazin-1-ylcarbonyl)ethyl]-5,6-diphenylpyridazin-3(2H)-one top
Crystal data top
C30H30N4O2F(000) = 1016
Mr = 478.58Dx = 1.259 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32998 reflections
a = 15.6725 (12) Åθ = 1.8–28.0°
b = 9.1139 (5) ŵ = 0.08 mm1
c = 17.6743 (12) ÅT = 296 K
β = 90.553 (6)°Plate, colourless
V = 2524.4 (3) Å30.73 × 0.51 × 0.11 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
4966 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3394 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.062
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.3°
rotation method scansh = 1919
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1111
Tmin = 0.477, Tmax = 0.907l = 2121
30083 measured 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0452P)2 + 0.0381P]
where P = (Fo2 + 2Fc2)/3
4966 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C30H30N4O2V = 2524.4 (3) Å3
Mr = 478.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.6725 (12) ŵ = 0.08 mm1
b = 9.1139 (5) ÅT = 296 K
c = 17.6743 (12) Å0.73 × 0.51 × 0.11 mm
β = 90.553 (6)°
Data collection top
Stoe IPDS-2
diffractometer
4966 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
3394 reflections with I > 2σ(I)
Tmin = 0.477, Tmax = 0.907Rint = 0.062
30083 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.03Δρmax = 0.14 e Å3
4966 reflectionsΔρmin = 0.15 e Å3
325 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
O10.77910 (7)0.86642 (13)0.78316 (6)0.0564 (4)
O20.75320 (8)0.76212 (12)0.50119 (6)0.0545 (4)
N10.65740 (8)0.85831 (14)0.71319 (7)0.0435 (4)
N20.57156 (8)0.85469 (13)0.70467 (7)0.0429 (4)
N30.83628 (9)0.57588 (14)0.54110 (7)0.0483 (4)
N40.89677 (9)0.28978 (14)0.50320 (7)0.0512 (5)
C10.70100 (10)0.85822 (16)0.78161 (8)0.0430 (5)
C20.64657 (10)0.84702 (16)0.84615 (8)0.0429 (5)
C30.56060 (9)0.84191 (14)0.84000 (8)0.0380 (4)
C40.52408 (9)0.84847 (15)0.76493 (8)0.0378 (4)
C50.43077 (9)0.84729 (15)0.74879 (8)0.0383 (4)
C60.37801 (11)0.73728 (17)0.77581 (9)0.0490 (5)
C70.29174 (12)0.73806 (19)0.75865 (10)0.0568 (6)
C80.25695 (11)0.84874 (19)0.71553 (10)0.0568 (6)
C90.30880 (12)0.95805 (19)0.68845 (10)0.0570 (6)
C100.39510 (11)0.95668 (17)0.70496 (9)0.0481 (5)
C110.50675 (9)0.82763 (15)0.90846 (8)0.0391 (4)
C120.52513 (11)0.72082 (17)0.96183 (9)0.0498 (5)
C130.47574 (13)0.7070 (2)1.02585 (9)0.0591 (6)
C140.40832 (12)0.8005 (2)1.03718 (10)0.0605 (6)
C150.39035 (11)0.90860 (19)0.98546 (9)0.0538 (6)
C160.43914 (10)0.92255 (17)0.92135 (8)0.0454 (5)
C170.70489 (11)0.85361 (17)0.64203 (8)0.0490 (5)
C180.74754 (11)0.70578 (16)0.63244 (8)0.0481 (5)
C190.78017 (10)0.68481 (16)0.55269 (8)0.0410 (5)
C200.86743 (11)0.54334 (17)0.46501 (8)0.0486 (5)
C210.85466 (11)0.38316 (17)0.44691 (9)0.0485 (5)
C220.86159 (14)0.32222 (19)0.57767 (10)0.0624 (6)
C230.87401 (13)0.4804 (2)0.59858 (9)0.0624 (7)
C240.88493 (13)0.13378 (18)0.48756 (11)0.0628 (7)
C250.93064 (11)0.07611 (16)0.41898 (9)0.0476 (5)
C261.00083 (12)0.14359 (18)0.38788 (10)0.0566 (6)
C271.04082 (13)0.0836 (2)0.32604 (11)0.0674 (7)
C281.01149 (16)0.0452 (2)0.29468 (11)0.0732 (8)
C290.94303 (15)0.1147 (2)0.32600 (12)0.0724 (8)
C300.90291 (12)0.05462 (18)0.38750 (11)0.0580 (6)
H20.671400.843100.894100.0510*
H60.400800.662600.805600.0590*
H70.257000.663100.776400.0680*
H80.198800.849700.704700.0680*
H90.285701.033000.659000.0680*
H100.429701.030800.686200.0580*
H120.571000.657900.954600.0600*
H130.488200.634401.061200.0710*
H140.374800.790401.080000.0730*
H150.345200.972600.993600.0650*
H160.426700.996100.886500.0540*
H17A0.747800.930300.642100.0590*
H17B0.666200.871200.599900.0590*
H18A0.707000.628700.643900.0580*
H18B0.794800.697700.668000.0580*
H20A0.927600.567500.462100.0580*
H20B0.836900.602900.428200.0580*
H21A0.794100.361300.445600.0580*
H21B0.877600.362300.397300.0580*
H22A0.889300.260600.615300.0750*
H22B0.801100.299400.577500.0750*
H23A0.847600.499500.647000.0750*
H23B0.934500.501300.603500.0750*
H24A0.824400.115100.481100.0750*
H24B0.904200.078600.531400.0750*
H261.021400.230400.408800.0680*
H271.087900.130500.305400.0810*
H281.038000.084800.252500.0880*
H290.923600.202800.305600.0870*
H300.856300.102700.408300.0700*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0356 (7)0.0821 (8)0.0516 (6)0.0029 (6)0.0057 (5)0.0074 (6)
O20.0572 (8)0.0642 (7)0.0423 (6)0.0168 (6)0.0084 (5)0.0007 (5)
N10.0377 (7)0.0554 (7)0.0374 (6)0.0085 (6)0.0074 (5)0.0026 (6)
N20.0392 (7)0.0508 (7)0.0386 (7)0.0076 (6)0.0029 (6)0.0026 (5)
N30.0500 (8)0.0562 (7)0.0388 (7)0.0133 (6)0.0059 (6)0.0037 (6)
N40.0533 (9)0.0515 (7)0.0488 (8)0.0122 (6)0.0070 (6)0.0015 (6)
C10.0388 (9)0.0487 (8)0.0416 (8)0.0071 (7)0.0022 (7)0.0051 (7)
C20.0416 (9)0.0529 (8)0.0341 (7)0.0067 (7)0.0008 (6)0.0043 (6)
C30.0402 (9)0.0367 (7)0.0371 (7)0.0055 (6)0.0033 (6)0.0021 (6)
C40.0396 (8)0.0372 (7)0.0366 (8)0.0051 (6)0.0037 (6)0.0012 (6)
C50.0388 (8)0.0420 (7)0.0342 (7)0.0034 (6)0.0022 (6)0.0048 (6)
C60.0466 (10)0.0452 (8)0.0551 (9)0.0012 (7)0.0026 (7)0.0055 (7)
C70.0461 (10)0.0561 (10)0.0683 (11)0.0091 (8)0.0007 (8)0.0012 (9)
C80.0397 (10)0.0632 (10)0.0674 (11)0.0031 (8)0.0076 (8)0.0086 (9)
C90.0513 (11)0.0553 (9)0.0640 (11)0.0079 (8)0.0126 (9)0.0052 (8)
C100.0446 (9)0.0486 (9)0.0509 (9)0.0012 (7)0.0028 (7)0.0039 (7)
C110.0379 (8)0.0458 (8)0.0337 (7)0.0012 (6)0.0020 (6)0.0024 (6)
C120.0521 (10)0.0534 (9)0.0440 (9)0.0074 (8)0.0029 (7)0.0014 (7)
C130.0657 (12)0.0676 (10)0.0441 (9)0.0003 (9)0.0070 (8)0.0124 (8)
C140.0550 (11)0.0813 (12)0.0455 (9)0.0051 (10)0.0153 (8)0.0001 (9)
C150.0413 (10)0.0713 (10)0.0489 (9)0.0076 (8)0.0083 (8)0.0077 (8)
C160.0421 (9)0.0524 (8)0.0417 (8)0.0069 (7)0.0016 (7)0.0003 (7)
C170.0487 (10)0.0600 (9)0.0385 (8)0.0092 (8)0.0117 (7)0.0013 (7)
C180.0501 (10)0.0519 (9)0.0426 (8)0.0015 (7)0.0098 (7)0.0071 (7)
C190.0350 (8)0.0467 (8)0.0413 (8)0.0018 (6)0.0038 (6)0.0056 (7)
C200.0472 (10)0.0557 (9)0.0432 (8)0.0099 (7)0.0115 (7)0.0024 (7)
C210.0462 (10)0.0566 (9)0.0427 (8)0.0080 (7)0.0054 (7)0.0028 (7)
C220.0721 (13)0.0687 (11)0.0465 (9)0.0236 (9)0.0087 (9)0.0087 (8)
C230.0660 (13)0.0771 (12)0.0439 (9)0.0254 (10)0.0028 (8)0.0051 (8)
C240.0664 (12)0.0523 (10)0.0699 (12)0.0077 (8)0.0195 (10)0.0062 (9)
C250.0438 (9)0.0430 (8)0.0560 (9)0.0066 (7)0.0039 (7)0.0052 (7)
C260.0504 (11)0.0491 (9)0.0704 (11)0.0015 (8)0.0078 (9)0.0006 (8)
C270.0567 (12)0.0738 (12)0.0721 (12)0.0094 (10)0.0182 (10)0.0148 (10)
C280.0857 (16)0.0784 (13)0.0557 (11)0.0254 (12)0.0058 (11)0.0058 (10)
C290.0785 (16)0.0632 (11)0.0754 (13)0.0039 (10)0.0073 (12)0.0143 (10)
C300.0475 (11)0.0512 (9)0.0751 (12)0.0004 (8)0.0013 (9)0.0040 (9)
Geometric parameters (Å, º) top
O1—C11.2263 (19)C25—C301.383 (2)
O2—C191.2232 (18)C26—C271.378 (3)
N1—N21.3527 (18)C27—C281.375 (3)
N1—C11.3832 (19)C28—C291.368 (3)
N1—C171.468 (2)C29—C301.375 (3)
N2—C41.3064 (19)C2—H20.9300
N3—C191.343 (2)C6—H60.9300
N3—C201.4655 (19)C7—H70.9300
N3—C231.459 (2)C8—H80.9300
N4—C211.462 (2)C9—H90.9300
N4—C221.462 (2)C10—H100.9300
N4—C241.460 (2)C12—H120.9300
C1—C21.435 (2)C13—H130.9300
C2—C31.352 (2)C14—H140.9300
C3—C41.441 (2)C15—H150.9300
C3—C111.488 (2)C16—H160.9300
C4—C51.487 (2)C17—H17A0.9700
C5—C61.387 (2)C17—H17B0.9700
C5—C101.378 (2)C18—H18A0.9700
C6—C71.383 (3)C18—H18B0.9700
C7—C81.374 (2)C20—H20A0.9700
C8—C91.375 (2)C20—H20B0.9700
C9—C101.381 (3)C21—H21A0.9700
C11—C121.384 (2)C21—H21B0.9700
C11—C161.388 (2)C22—H22A0.9700
C12—C131.383 (2)C22—H22B0.9700
C13—C141.374 (3)C23—H23A0.9700
C14—C151.371 (2)C23—H23B0.9700
C15—C161.379 (2)C24—H24A0.9700
C17—C181.514 (2)C24—H24B0.9700
C18—C191.516 (2)C26—H260.9300
C20—C211.507 (2)C27—H270.9300
C22—C231.501 (3)C28—H280.9300
C24—C251.509 (3)C29—H290.9300
C25—C261.379 (2)C30—H300.9300
O1···C183.0755 (18)H6···N2vii2.8500
O2···C2i3.3470 (19)H7···C1vii3.0400
O1···H17A2.6000H7···H17Avii2.5700
O1···H27ii2.6200H8···C25ix3.0400
O1···H20Biii2.7200H8···C30ix2.9400
O1···H29iv2.7400H9···C2vi3.0500
O1···H18B2.5600H9···C30ix3.0700
O2···H20B2.3500H9···H30ix2.5900
O2···H30v2.6200H10···N22.7600
O2···H17B2.4400H10···C3vi2.8800
O2···H2i2.4700H12···C22.8400
N3···N42.8564 (18)H12···H22.5500
N4···N32.8564 (18)H13···N2iii2.8400
N1···H6vi2.9400H13···C10iii3.0600
N2···H13i2.8400H15···C19vi2.8700
N2···H102.7600H16···C42.9700
N2···H6vi2.8500H16···C52.7900
N4···H262.6400H16···H18Avi2.4700
C1···C7vi3.536 (2)H17A···O12.6000
C2···O2iii3.3470 (19)H17A···H7vi2.5700
C5···C163.128 (2)H17B···O22.4400
C6···C163.215 (2)H18A···C233.0600
C6···C113.187 (2)H18A···H23A2.5000
C7···C1vii3.536 (2)H18A···H16vii2.4700
C11···C63.187 (2)H18B···O12.5600
C11···C15viii3.441 (2)H18B···C12.9000
C14···C16viii3.548 (2)H18B···C232.6500
C15···C16viii3.484 (2)H18B···H23A2.0200
C15···C11viii3.441 (2)H18B···H27ii2.4600
C16···C53.128 (2)H20A···H23B2.5700
C16···C15viii3.484 (2)H20A···H23Bii2.5400
C16···C14viii3.548 (2)H20B···O22.3500
C16···C63.215 (2)H20B···O1i2.7200
C18···O13.0755 (18)H21A···H22B2.4000
C21···C263.339 (2)H21A···H24A2.3800
C26···C213.339 (2)H21B···C252.7600
C1···H18B2.9000H21B···C262.7800
C1···H7vi3.0400H21B···H262.5600
C2···H122.8400H22A···H24B2.2400
C2···H9vii3.0500H22A···C28x2.9600
C3···H10vii2.8800H22B···H21A2.4000
C3···H63.0500H22B···H24A2.4200
C4···H162.9700H23A···C182.4600
C5···H162.7900H23A···H18A2.5000
C10···H13i3.0600H23A···H18B2.0200
C11···H62.8800H23B···H20A2.5700
C12···H22.8300H23B···H20Aii2.5400
C18···H23A2.4600H23B···H26ii2.5500
C19···H15vii2.8700H24A···H21A2.3800
C21···H263.0400H24A···H22B2.4200
C23···H18A3.0600H24A···H302.4200
C23···H18B2.6500H24B···H22A2.2400
C25···H8ix3.0400H24B···C25x3.0700
C25···H24Bx3.0700H24B···C26x2.8800
C25···H21B2.7600H24B···C27x3.0400
C26···H21B2.7800H26···N42.6400
C26···H24Bx2.8800H26···C213.0400
C27···H29xi3.0900H26···H21B2.5600
C27···H24Bx3.0400H26···H23Bii2.5500
C28···H22Ax2.9600H27···H29xi2.4900
C30···H8ix2.9400H27···O1ii2.6200
C30···H9ix3.0700H27···H18Bii2.4600
H2···C122.8300H29···C27xii3.0900
H2···H122.5500H29···H27xii2.4900
H2···O2iii2.4700H29···O1xiii2.7400
H6···C33.0500H30···O2xiv2.6200
H6···C112.8800H30···H24A2.4200
H6···N1vii2.9400H30···H9ix2.5900
N2—N1—C1125.43 (12)C9—C8—H8120.00
N2—N1—C17114.57 (12)C8—C9—H9120.00
C1—N1—C17119.91 (13)C10—C9—H9120.00
N1—N2—C4118.95 (12)C5—C10—H10119.00
C19—N3—C20120.92 (13)C9—C10—H10119.00
C19—N3—C23126.61 (13)C11—C12—H12120.00
C20—N3—C23112.46 (13)C13—C12—H12120.00
C21—N4—C22108.86 (13)C12—C13—H13120.00
C21—N4—C24112.48 (13)C14—C13—H13120.00
C22—N4—C24108.60 (13)C13—C14—H14120.00
O1—C1—N1120.27 (13)C15—C14—H14120.00
O1—C1—C2125.99 (14)C14—C15—H15120.00
N1—C1—C2113.74 (13)C16—C15—H15120.00
C1—C2—C3122.58 (13)C11—C16—H16120.00
C2—C3—C4117.35 (13)C15—C16—H16120.00
C2—C3—C11120.70 (13)N1—C17—H17A110.00
C4—C3—C11121.94 (12)N1—C17—H17B110.00
N2—C4—C3121.88 (13)C18—C17—H17A110.00
N2—C4—C5114.25 (12)C18—C17—H17B110.00
C3—C4—C5123.87 (13)H17A—C17—H17B108.00
C4—C5—C6121.83 (13)C17—C18—H18A109.00
C4—C5—C10119.70 (13)C17—C18—H18B109.00
C6—C5—C10118.46 (14)C19—C18—H18A109.00
C5—C6—C7120.37 (15)C19—C18—H18B109.00
C6—C7—C8120.49 (16)H18A—C18—H18B108.00
C7—C8—C9119.50 (17)N3—C20—H20A110.00
C8—C9—C10120.06 (16)N3—C20—H20B110.00
C5—C10—C9121.11 (15)C21—C20—H20A110.00
C3—C11—C12120.00 (13)C21—C20—H20B110.00
C3—C11—C16121.25 (12)H20A—C20—H20B108.00
C12—C11—C16118.73 (14)N4—C21—H21A109.00
C11—C12—C13120.49 (15)N4—C21—H21B109.00
C12—C13—C14120.02 (16)C20—C21—H21A109.00
C13—C14—C15120.12 (16)C20—C21—H21B109.00
C14—C15—C16120.13 (16)H21A—C21—H21B108.00
C11—C16—C15120.50 (14)N4—C22—H22A109.00
N1—C17—C18110.48 (12)N4—C22—H22B109.00
C17—C18—C19111.68 (12)C23—C22—H22A109.00
O2—C19—N3122.30 (14)C23—C22—H22B109.00
O2—C19—C18120.13 (14)H22A—C22—H22B108.00
N3—C19—C18117.52 (13)N3—C23—H23A110.00
N3—C20—C21110.24 (13)N3—C23—H23B110.00
N4—C21—C20111.18 (13)C22—C23—H23A110.00
N4—C22—C23111.52 (14)C22—C23—H23B110.00
N3—C23—C22110.54 (14)H23A—C23—H23B108.00
N4—C24—C25115.53 (14)N4—C24—H24A108.00
C24—C25—C26123.48 (15)N4—C24—H24B108.00
C24—C25—C30118.26 (15)C25—C24—H24A108.00
C26—C25—C30118.20 (16)C25—C24—H24B108.00
C25—C26—C27120.65 (16)H24A—C24—H24B107.00
C26—C27—C28120.36 (19)C25—C26—H26120.00
C27—C28—C29119.52 (19)C27—C26—H26120.00
C28—C29—C30120.14 (18)C26—C27—H27120.00
C25—C30—C29121.12 (17)C28—C27—H27120.00
C1—C2—H2119.00C27—C28—H28120.00
C3—C2—H2119.00C29—C28—H28120.00
C5—C6—H6120.00C28—C29—H29120.00
C7—C6—H6120.00C30—C29—H29120.00
C6—C7—H7120.00C25—C30—H30119.00
C8—C7—H7120.00C29—C30—H30119.00
C7—C8—H8120.00
C1—N1—N2—C41.0 (2)C3—C4—C5—C10126.30 (15)
C17—N1—N2—C4175.45 (13)N2—C4—C5—C1054.31 (18)
N2—N1—C1—O1177.67 (14)N2—C4—C5—C6124.74 (15)
C17—N1—C1—O16.0 (2)C3—C4—C5—C654.7 (2)
N2—N1—C1—C22.7 (2)C6—C5—C10—C90.4 (2)
C17—N1—C1—C2173.61 (13)C10—C5—C6—C70.2 (2)
N2—N1—C17—C18107.77 (14)C4—C5—C10—C9179.48 (15)
C1—N1—C17—C1868.93 (17)C4—C5—C6—C7178.86 (14)
N1—N2—C4—C31.5 (2)C5—C6—C7—C80.9 (3)
N1—N2—C4—C5179.11 (12)C6—C7—C8—C91.0 (3)
C20—N3—C19—O20.7 (2)C7—C8—C9—C100.4 (3)
C23—N3—C19—O2178.20 (16)C8—C9—C10—C50.3 (3)
C23—N3—C20—C2153.97 (18)C12—C11—C16—C151.2 (2)
C19—N3—C20—C21127.01 (15)C3—C11—C16—C15179.40 (14)
C23—N3—C19—C184.4 (2)C3—C11—C12—C13179.70 (15)
C19—N3—C23—C22127.24 (17)C16—C11—C12—C131.5 (2)
C20—N3—C19—C18176.74 (14)C11—C12—C13—C140.6 (3)
C20—N3—C23—C2253.8 (2)C12—C13—C14—C150.6 (3)
C24—N4—C21—C20179.51 (14)C13—C14—C15—C160.9 (3)
C21—N4—C22—C2358.98 (19)C14—C15—C16—C110.0 (3)
C22—N4—C21—C2059.10 (17)N1—C17—C18—C19167.27 (13)
C24—N4—C22—C23178.24 (16)C17—C18—C19—N3164.55 (14)
C22—N4—C24—C25170.09 (16)C17—C18—C19—O218.0 (2)
C21—N4—C24—C2569.35 (19)N3—C20—C21—N456.76 (18)
N1—C1—C2—C32.0 (2)N4—C22—C23—N356.5 (2)
O1—C1—C2—C3178.38 (15)N4—C24—C25—C2622.2 (2)
C1—C2—C3—C11178.92 (13)N4—C24—C25—C30160.63 (16)
C1—C2—C3—C40.1 (2)C24—C25—C26—C27178.65 (17)
C11—C3—C4—C52.3 (2)C30—C25—C26—C271.4 (3)
C2—C3—C4—C5178.64 (13)C24—C25—C30—C29178.55 (18)
C2—C3—C11—C1249.2 (2)C26—C25—C30—C291.2 (3)
C2—C3—C11—C16128.97 (15)C25—C26—C27—C280.4 (3)
C4—C3—C11—C12129.80 (15)C26—C27—C28—C291.0 (3)
C4—C3—C11—C1652.04 (19)C27—C28—C29—C301.2 (3)
C11—C3—C4—N2177.02 (13)C28—C29—C30—C250.1 (3)
C2—C3—C4—N22.0 (2)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+2, y+1, z+1; (iii) x, y+3/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x, y+1, z; (vi) x+1, y+1/2, z+3/2; (vii) x+1, y1/2, z+3/2; (viii) x+1, y+2, z+2; (ix) x+1, y+1, z+1; (x) x+2, y, z+1; (xi) x+2, y+1/2, z+1/2; (xii) x+2, y1/2, z+1/2; (xiii) x, y+1/2, z1/2; (xiv) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2iii0.932.473.3470 (19)157
C18—H18B···O10.972.563.0755 (18)113
C20—H20B···O20.972.352.759 (2)105
Symmetry code: (iii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC30H30N4O2
Mr478.58
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)15.6725 (12), 9.1139 (5), 17.6743 (12)
β (°) 90.553 (6)
V3)2524.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.73 × 0.51 × 0.11
Data collection
DiffractometerStoe IPDS2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.477, 0.907
No. of measured, independent and
observed [I > 2σ(I)] reflections
30083, 4966, 3394
Rint0.062
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.094, 1.03
No. of reflections4966
No. of parameters325
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.15

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
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.473.3470 (19)157
C18—H18B···O10.972.563.0755 (18)113
C20—H20B···O20.972.352.759 (2)105
Symmetry code: (i) x, y+3/2, z+1/2.
 

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

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First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
First citationSwenson, D. C., Yamamoto, M. & Burton, D. J. (1997). Acta Cryst. C53, 1445–1447.  CSD CrossRef CAS Web of Science IUCr Journals
First citationYüksektepe, Ç., Saraçoğlu, H., Koca, M., Çukurovali, A. & Çalışkan, N. (2004). Acta Cryst. C60, o509–o510.  CSD CrossRef IUCr Journals

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