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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Fluoro-3-phenyl-N′-(4-propyl­cyclo­hexyl­­idene)-1H-indole-2-carbohydrazide

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 1 July 2013; accepted 2 July 2013; online 6 July 2013)

In the title compound, C24H26FN3O, the cyclo­hexane ring adopts a chair conformation; the propyl substituent is in an equatorial orientation and the bond-angle sum at the C atom bonded to the carbohydrazide N atom is 360.0°. The dihedral angle between the 1H-indole ring system and the phenyl ring is 82.77 (13)°. A weak intra­molecular C—H⋯π contact occurs. In the crystal, pairs of mol­ecules related by a crystallographic twofold axis are linked by bifurcated N—H⋯(O,N) hydrogen bonds; a C—H⋯O inter­action occurs between the same pair. The dimers are linked by C—H⋯F and C—H⋯π inter­actions, generating a three-dimensional network.

Related literature

For the design and synthesis of indolylhydrazones and their cyclization products, spiro­thia­zolidinones, as potential anti­tuberculosis and anti­cancer agents, see: Akkurt et al. (2010[Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830.], 2013[Akkurt, M., Zopun, M., Çapan, G. & Büyükgüngör, O. (2013). Acta Cryst. E69, o1137.]); Cihan-Üstündağ & Çapan (2012[Cihan-Üstündağ, G. & Çapan, G. (2012). Mol. Divers. 16, 525-539.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26FN3O

  • Mr = 391.48

  • Tetragonal, [I \overline 4]

  • a = 22.6986 (11) Å

  • c = 8.4480 (5) Å

  • V = 4352.6 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.63 × 0.46 × 0.28 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.957, Tmax = 0.978

  • 15640 measured reflections

  • 4531 independent reflections

  • 3430 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.092

  • S = 1.03

  • 4531 reflections

  • 267 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.11 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the 1H-pyrrole (N1/C1/C6/C7/C14), benzene (C1–C6) and phenyl (C8–C13) rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.86 2.50 3.048 (4) 123
N1—H1⋯N3i 0.86 2.32 3.170 (3) 168
C2—H2⋯O1i 0.93 2.51 3.112 (4) 123
C5—H5⋯F1ii 0.93 2.52 3.383 (3) 154
C3—H3⋯Cg3iii 0.93 2.82 3.708 (3) 160
C11—H11⋯Cg1iv 0.93 2.89 3.683 (3) 144
C17—H17ACg2v 0.97 2.81 3.571 (3) 136
C17—H17BCg3 0.97 2.90 3.810 (4) 157
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) y+1, -x+1, -z+1; (iii) -y+1, x-1, -z+1; (iv) y+1, -x+1, -z; (v) 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: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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


Comment top

Recently our work has been focused on the design and synthesis of novel indolylhydrazones and their cyclization products spirothiazolidinones as potential antituberculosis and anticancer agents (Akkurt et al., 2010, 2013; Cihan-Üstündağ & Çapan, 2012). Within this context, we here report the synthesis and crystal structure of the title compound.

As shown in Fig. 1, the (C16–C21) cyclohexane ring of the title compound adopts a chair conformation with the puckering parameters of Q(T) = 0.540 (4) Å, θ = 176.6 (4) ° and ϕ = 129 (12) °. The 1H-indole ring system makes a dihedral angle of 82.77 (13) ° with the C8–C13 phenyl ring. The N1–C14–C15–O1, N1–C14–C15–N2, C14–C15–N2–N3, C15–N2–N3–C16, N2–N3–C16–C17 and C19–C22–C23–C24 torsion angles are 11.3 (4), -167.4 (3), 174.2 (2), 174.8 (3), -1.1 (5) and 176.7 (5) °, respectively.

In the crystal, molecules are linked by N—H···O, N—H···N, C—H···O, C—H···F hydrogen bonds, forming layers parallel to the (110) plane (Table 1, Fig. 2). In addition, C—H···π interactions also contribute to the cohesion of the crystal packing.

Related literature top

For the design and synthesis of indolylhydrazones and their cyclization products, spirothiazolidinones, as potential antituberculosis and anticancer agents, see: Akkurt et al. (2010, 2013); Cihan-Üstündağ & Çapan (2012). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (0.005 mol) and 4-propyl cyclohexanone (0.007 mol) was refluxed in 15 ml ethanol for 5 h. The precipitate obtained was purified by recrystallization from an ethanol-water mixture to yield colourless prisms.

Yield: 78%, mp.: 446–447.5 K. IR(KBr): υmax 3366, 3243 (N—H), 1690 (C=O) cm-1. 1H-NMR (DMSO-d6/500 MHz): δ 0.78–0.88 (m and t, 4H, J= 7.3 Hz, 4-CH2CH2CH3, CH/CH2-cyc.*), 1.04–1.07 (m, 1H, CH/CH2-cyc.), 1.15 (br. d, 2H, J=6.3 Hz, 4-CH2CH2CH3-cyc.), 1.27 (br. quin, 2H, 4-CH2CH2CH3-cyc.), 1.47 (br. d, 2H,J=14.9 Hz, CH/CH2-cyc.), 1.59 (d, 1H, J=12.7 Hz, CH/CH2-cyc.), 1.70–1.88 (m, 2H, CH/CH2-cyc.), 2.13 (s, 1H, CH/CH2-cyc.), 2.30 (s, 1H, CH/CH2-cyc.), 7.12 (br. t, 2H, J=8.8 Hz, H4, H6-ind.), 7.42–7.50 (m, 6H, H7, 3-C6H5-ind.), 9.44 (s, 1H, CONH), 12.02 (s, 1H, NH) p.p.m.. 13C-NMR (Proton decoupled, DMSO-d6/100 MHz): δ 14.61 (4-CH2CH2CH3-cyc.), 20.05 (4-CH2CH2CH3-cyc.), 25.83 (CH2-cyc.), 32.00 (CH2-cyc.), 33.03 (CH2-cyc.), 34.43 (CH2-cyc.), 35.91 (CH-cyc.), 38.18 (4-CH2CH2CH3-cyc.), 105.02 (d, J=23.7 Hz, C4-ind.), 113.17 (d, J=26.0 Hz, C6-ind.), 114.28 (C7-ind.), 117.96 (C3-ind.), 127.36 (d, C3a-ind.), 127.89 (3-C6H5(C4)-ind.), 129.46 (3-C6H5(C3,C5)-ind.), 129.99 (C2-ind.), 130.53 (3-C6H5(C2,C6)-ind.), 132.79** (C7a-ind.), 133.72** (3-C6H5(C1)-ind.), 158.03 (C=N), 158.08 (d, J=233.6 Hz, C5-ind.), 161.94 (C=O) p.p.m.. MS (APCI+) m/z(%) 392 (MH+, 90). Analysis calculated for C24H26FN3O : C, 73.63; H, 6.69; N, 10.73%. Found: C, 73.43; H, 6.62; N, 10.51%.(*cyc.=cyclohexylidene, br.=broad, quin.=quintet, ind.=indole, ** interchangeable).

Refinement top

H atoms bonded to C atoms and the H atom (N1)H1 of the one of the two amide groups were positioned geometrically with C—H = 0.93 - 0.98 Å, and N—H = 0.86 Å and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C,N). The H atom (N2)H2A of the second groups were found in a difference Fourier map, restrained with N—H = 0.86 (2) Å and refined with Uiso = 1.2Ueq(N). The absolute structure was indeterminate in the present experiment.

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: SHELXS97 (Sheldrick, 2008); 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 molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the packing and hydrogen bondings of the title compound, down the [001]-axis. H atoms not participating in hydrogen bonding have been omitted for clarity.
5-Fluoro-3-phenyl-N'-(4-propylcyclohexylidene)-1H-indole-2-carbohydrazide top
Crystal data top
C24H26FN3ODx = 1.195 Mg m3
Mr = 391.48Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4Cell parameters from 20884 reflections
Hall symbol: I -4θ = 2.5–27.4°
a = 22.6986 (11) ŵ = 0.08 mm1
c = 8.4480 (5) ÅT = 296 K
V = 4352.6 (5) Å3Prism, colourless
Z = 80.63 × 0.46 × 0.28 mm
F(000) = 1664
Data collection top
Stoe IPDS 2
diffractometer
4531 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3430 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.066
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.5°
ω–scansh = 2827
Absorption correction: integration
(Stoe & Cie, 2002)
k = 2828
Tmin = 0.957, Tmax = 0.978l = 1010
15640 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 W = 1/[Σ2(FO2) + (0.0396P)2 + 0.3772P] WHERE P = (FO2 + 2FC2)/3
S = 1.03(Δ/σ)max < 0.001
4531 reflectionsΔρmax = 0.13 e Å3
267 parametersΔρmin = 0.11 e Å3
Crystal data top
C24H26FN3OZ = 8
Mr = 391.48Mo Kα radiation
Tetragonal, I4µ = 0.08 mm1
a = 22.6986 (11) ÅT = 296 K
c = 8.4480 (5) Å0.63 × 0.46 × 0.28 mm
V = 4352.6 (5) Å3
Data collection top
Stoe IPDS 2
diffractometer
4531 independent reflections
Absorption correction: integration
(Stoe & Cie, 2002)
3430 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.978Rint = 0.066
15640 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0472 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.13 e Å3
4531 reflectionsΔρmin = 0.11 e Å3
267 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
F10.95641 (9)0.05822 (8)0.6774 (3)0.0742 (7)
O10.77085 (10)0.26762 (14)0.0944 (4)0.1013 (11)
N10.80598 (10)0.18855 (10)0.3230 (3)0.0513 (8)
N20.84810 (11)0.24602 (12)0.0590 (3)0.0588 (9)
N30.83121 (11)0.28546 (12)0.1750 (3)0.0608 (9)
C10.83656 (11)0.15385 (12)0.4270 (4)0.0476 (9)
C20.82036 (14)0.13032 (13)0.5733 (4)0.0587 (10)
C30.86172 (14)0.09835 (13)0.6542 (4)0.0605 (11)
C40.91761 (14)0.09077 (12)0.5911 (4)0.0559 (10)
C50.93519 (12)0.11312 (12)0.4498 (4)0.0507 (9)
C60.89358 (11)0.14621 (11)0.3643 (3)0.0432 (8)
C70.89623 (11)0.17781 (11)0.2192 (3)0.0428 (8)
C80.94986 (11)0.18498 (11)0.1185 (3)0.0443 (9)
C90.96716 (13)0.14270 (14)0.0110 (4)0.0584 (11)
C101.01697 (14)0.15077 (16)0.0816 (4)0.0665 (11)
C111.05025 (13)0.20044 (16)0.0662 (4)0.0667 (11)
C121.03435 (15)0.24189 (17)0.0407 (5)0.0777 (14)
C130.98449 (13)0.23467 (14)0.1336 (4)0.0634 (11)
C140.84140 (11)0.20304 (11)0.1986 (3)0.0465 (9)
C150.81674 (12)0.24211 (14)0.0752 (4)0.0566 (10)
C160.86492 (14)0.29068 (14)0.2948 (4)0.0592 (11)
C170.92192 (15)0.26047 (14)0.3283 (4)0.0687 (11)
C180.97104 (15)0.30538 (16)0.3529 (4)0.0723 (12)
C190.95600 (16)0.35201 (15)0.4750 (4)0.0673 (11)
C200.89727 (17)0.38012 (17)0.4386 (5)0.0780 (12)
C210.84788 (16)0.33486 (19)0.4175 (5)0.0830 (14)
C221.0046 (2)0.3974 (2)0.4948 (5)0.0937 (16)
C231.0627 (2)0.3747 (3)0.5558 (8)0.131 (3)
C241.1078 (3)0.4215 (4)0.5818 (8)0.169 (4)
H10.770000.199500.334400.0620*
H20.782800.136200.614400.0700*
H2A0.8751 (11)0.2227 (12)0.060 (3)0.060 (9)*
H30.852300.081700.751500.0730*
H50.973000.106800.411200.0610*
H90.945200.108300.000500.0700*
H101.027700.122100.154700.0800*
H111.083600.205800.128600.0800*
H121.057100.275700.052000.0930*
H130.974300.263500.206800.0760*
H17A0.917900.236300.422400.0830*
H17B0.931900.234800.240400.0830*
H18A0.979500.324500.252800.0870*
H18B1.006400.284900.386200.0870*
H190.951800.331800.576800.0810*
H20A0.886900.406700.524000.0930*
H20B0.900800.403200.342500.0930*
H21A0.811900.354700.385600.1000*
H21B0.840500.315000.517300.1000*
H22A0.990700.427700.566700.1130*
H22B1.011400.416000.393100.1130*
H23A1.078200.346300.480900.1570*
H23B1.056000.354300.655000.1570*
H24A1.116100.440900.483300.2030*
H24B1.093100.449700.656800.2030*
H24C1.143300.404000.622000.2030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0820 (13)0.0652 (11)0.0755 (13)0.0059 (9)0.0167 (10)0.0183 (10)
O10.0639 (15)0.135 (2)0.105 (2)0.0507 (15)0.0263 (15)0.0539 (19)
N10.0347 (11)0.0569 (14)0.0623 (15)0.0076 (10)0.0116 (11)0.0062 (12)
N20.0488 (14)0.0670 (16)0.0605 (16)0.0165 (13)0.0026 (13)0.0149 (14)
N30.0486 (13)0.0740 (17)0.0599 (16)0.0073 (12)0.0061 (14)0.0195 (14)
C10.0434 (14)0.0435 (14)0.0558 (17)0.0010 (11)0.0067 (14)0.0004 (14)
C20.0553 (17)0.0578 (17)0.0630 (19)0.0022 (14)0.0196 (16)0.0060 (16)
C30.074 (2)0.0535 (17)0.0540 (18)0.0014 (15)0.0104 (17)0.0073 (15)
C40.0631 (19)0.0438 (16)0.0609 (19)0.0019 (13)0.0076 (16)0.0050 (15)
C50.0426 (14)0.0480 (15)0.0616 (18)0.0028 (12)0.0002 (14)0.0011 (14)
C60.0405 (14)0.0390 (13)0.0502 (15)0.0013 (11)0.0035 (12)0.0029 (12)
C70.0364 (13)0.0437 (14)0.0483 (16)0.0026 (11)0.0025 (12)0.0005 (12)
C80.0336 (13)0.0507 (15)0.0487 (17)0.0053 (11)0.0003 (12)0.0087 (13)
C90.0444 (16)0.0658 (19)0.065 (2)0.0009 (14)0.0054 (15)0.0084 (16)
C100.0536 (18)0.084 (2)0.062 (2)0.0113 (16)0.0098 (16)0.0081 (18)
C110.0432 (16)0.087 (2)0.070 (2)0.0038 (16)0.0174 (16)0.014 (2)
C120.060 (2)0.066 (2)0.107 (3)0.0134 (17)0.020 (2)0.013 (2)
C130.0551 (18)0.0540 (17)0.081 (2)0.0016 (14)0.0174 (17)0.0034 (16)
C140.0390 (14)0.0482 (15)0.0523 (16)0.0023 (12)0.0038 (13)0.0020 (13)
C150.0379 (14)0.0648 (18)0.067 (2)0.0075 (13)0.0065 (15)0.0128 (16)
C160.0519 (17)0.0660 (19)0.0596 (19)0.0019 (15)0.0097 (16)0.0107 (16)
C170.078 (2)0.0631 (19)0.065 (2)0.0053 (16)0.0121 (18)0.0046 (18)
C180.060 (2)0.088 (2)0.069 (2)0.0106 (17)0.0040 (18)0.015 (2)
C190.070 (2)0.075 (2)0.0570 (19)0.0035 (17)0.0010 (16)0.0060 (17)
C200.085 (2)0.079 (2)0.070 (2)0.0109 (19)0.002 (2)0.024 (2)
C210.064 (2)0.109 (3)0.076 (2)0.0032 (19)0.0066 (19)0.034 (2)
C220.095 (3)0.109 (3)0.077 (2)0.022 (2)0.005 (2)0.022 (2)
C230.084 (3)0.169 (5)0.139 (5)0.026 (3)0.007 (3)0.047 (4)
C240.113 (4)0.272 (9)0.122 (5)0.080 (5)0.013 (4)0.074 (5)
Geometric parameters (Å, º) top
F1—C41.361 (4)C19—C221.519 (6)
O1—C151.203 (4)C19—C201.510 (5)
N1—C11.369 (4)C20—C211.531 (6)
N1—C141.364 (4)C22—C231.507 (7)
N2—N31.382 (4)C23—C241.492 (10)
N2—C151.342 (4)C2—H20.9300
N3—C161.274 (4)C3—H30.9300
N1—H10.8600C5—H50.9300
N2—H2A0.81 (3)C9—H90.9300
C1—C21.396 (5)C10—H100.9300
C1—C61.409 (4)C11—H110.9300
C2—C31.369 (4)C12—H120.9300
C3—C41.387 (5)C13—H130.9300
C4—C51.357 (5)C17—H17A0.9700
C5—C61.406 (4)C17—H17B0.9700
C6—C71.422 (4)C18—H18A0.9700
C7—C81.494 (4)C18—H18B0.9700
C7—C141.381 (4)C19—H190.9800
C8—C91.378 (4)C20—H20A0.9700
C8—C131.381 (4)C20—H20B0.9700
C9—C101.387 (4)C21—H21A0.9700
C10—C111.363 (5)C21—H21B0.9700
C11—C121.353 (5)C22—H22A0.9700
C12—C131.387 (5)C22—H22B0.9700
C14—C151.479 (4)C23—H23A0.9700
C16—C211.493 (5)C23—H23B0.9700
C16—C171.491 (5)C24—H24A0.9600
C17—C181.525 (5)C24—H24B0.9600
C18—C191.517 (5)C24—H24C0.9600
C1—N1—C14109.5 (2)C4—C5—H5122.00
N3—N2—C15119.7 (3)C6—C5—H5121.00
N2—N3—C16117.2 (3)C8—C9—H9120.00
C1—N1—H1125.00C10—C9—H9120.00
C14—N1—H1125.00C9—C10—H10120.00
N3—N2—H2A128.8 (18)C11—C10—H10120.00
C15—N2—H2A111.5 (18)C10—C11—H11120.00
N1—C1—C6107.2 (3)C12—C11—H11120.00
C2—C1—C6121.9 (3)C11—C12—H12120.00
N1—C1—C2130.9 (3)C13—C12—H12120.00
C1—C2—C3117.7 (3)C8—C13—H13120.00
C2—C3—C4120.1 (3)C12—C13—H13120.00
F1—C4—C3117.0 (3)C16—C17—H17A110.00
C3—C4—C5124.1 (3)C16—C17—H17B109.00
F1—C4—C5118.9 (3)C18—C17—H17A110.00
C4—C5—C6117.0 (3)C18—C17—H17B110.00
C1—C6—C5119.3 (3)H17A—C17—H17B108.00
C5—C6—C7133.2 (2)C17—C18—H18A109.00
C1—C6—C7107.5 (2)C17—C18—H18B109.00
C6—C7—C14106.3 (2)C19—C18—H18A109.00
C8—C7—C14128.1 (2)C19—C18—H18B109.00
C6—C7—C8125.5 (2)H18A—C18—H18B108.00
C7—C8—C13120.0 (2)C18—C19—H19107.00
C9—C8—C13117.9 (3)C20—C19—H19107.00
C7—C8—C9122.1 (2)C22—C19—H19107.00
C8—C9—C10120.8 (3)C19—C20—H20A109.00
C9—C10—C11120.5 (3)C19—C20—H20B109.00
C10—C11—C12119.4 (3)C21—C20—H20A109.00
C11—C12—C13120.9 (3)C21—C20—H20B109.00
C8—C13—C12120.6 (3)H20A—C20—H20B108.00
N1—C14—C15117.7 (2)C16—C21—H21A110.00
C7—C14—C15132.7 (2)C16—C21—H21B110.00
N1—C14—C7109.5 (2)C20—C21—H21A110.00
N2—C15—C14115.8 (2)C20—C21—H21B110.00
O1—C15—N2122.8 (3)H21A—C21—H21B108.00
O1—C15—C14121.4 (3)C19—C22—H22A108.00
N3—C16—C21117.3 (3)C19—C22—H22B108.00
C17—C16—C21113.7 (3)C23—C22—H22A108.00
N3—C16—C17129.0 (3)C23—C22—H22B108.00
C16—C17—C18110.7 (3)H22A—C22—H22B107.00
C17—C18—C19113.2 (3)C22—C23—H23A109.00
C18—C19—C20110.8 (3)C22—C23—H23B109.00
C18—C19—C22112.6 (3)C24—C23—H23A109.00
C20—C19—C22112.2 (3)C24—C23—H23B109.00
C19—C20—C21112.8 (3)H23A—C23—H23B108.00
C16—C21—C20110.0 (3)C23—C24—H24A109.00
C19—C22—C23116.2 (4)C23—C24—H24B109.00
C22—C23—C24114.1 (6)C23—C24—H24C109.00
C1—C2—H2121.00H24A—C24—H24B110.00
C3—C2—H2121.00H24A—C24—H24C109.00
C2—C3—H3120.00H24B—C24—H24C110.00
C4—C3—H3120.00
C1—N1—C14—C15178.2 (2)C14—C7—C8—C1379.6 (4)
C14—N1—C1—C2176.9 (3)C14—C7—C8—C9101.6 (3)
C14—N1—C1—C60.2 (3)C8—C7—C14—C152.2 (5)
C1—N1—C14—C70.0 (3)C6—C7—C8—C1395.4 (3)
C15—N2—N3—C16174.8 (3)C9—C8—C13—C121.3 (5)
N3—N2—C15—O17.1 (5)C7—C8—C13—C12179.9 (3)
N3—N2—C15—C14174.2 (2)C7—C8—C9—C10179.6 (3)
N2—N3—C16—C21177.8 (3)C13—C8—C9—C101.6 (4)
N2—N3—C16—C171.1 (5)C8—C9—C10—C111.0 (5)
C2—C1—C6—C7177.2 (3)C9—C10—C11—C120.2 (5)
N1—C1—C2—C3177.8 (3)C10—C11—C12—C130.5 (5)
C6—C1—C2—C31.0 (4)C11—C12—C13—C80.2 (5)
N1—C1—C6—C70.3 (3)N1—C14—C15—N2167.4 (3)
C2—C1—C6—C51.1 (4)C7—C14—C15—O1166.4 (3)
N1—C1—C6—C5178.6 (2)C7—C14—C15—N214.9 (5)
C1—C2—C3—C40.6 (4)N1—C14—C15—O111.3 (4)
C2—C3—C4—F1179.6 (3)N3—C16—C17—C18122.2 (4)
C2—C3—C4—C50.3 (5)C21—C16—C17—C1854.6 (4)
C3—C4—C5—C60.4 (4)N3—C16—C21—C20121.6 (3)
F1—C4—C5—C6179.7 (2)C17—C16—C21—C2055.6 (4)
C4—C5—C6—C7177.0 (3)C16—C17—C18—C1952.3 (4)
C4—C5—C6—C10.8 (4)C17—C18—C19—C2051.8 (4)
C5—C6—C7—C82.3 (5)C17—C18—C19—C22178.4 (3)
C1—C6—C7—C140.2 (3)C18—C19—C20—C2152.9 (4)
C5—C6—C7—C14178.2 (3)C22—C19—C20—C21179.7 (3)
C1—C6—C7—C8175.7 (2)C18—C19—C22—C2363.2 (5)
C6—C7—C14—N10.1 (3)C20—C19—C22—C23170.9 (4)
C6—C7—C8—C983.4 (4)C19—C20—C21—C1654.5 (4)
C6—C7—C14—C15178.0 (3)C19—C22—C23—C24176.7 (5)
C8—C7—C14—N1175.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the 1H-pyrrole (N1/C1/C6/C7/C14), benzene (C1–C6) and phenyl (C8–C13) rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.503.048 (4)123
N1—H1···N3i0.862.323.170 (3)168
C2—H2···O1i0.932.513.112 (4)123
C5—H5···F1ii0.932.523.383 (3)154
C3—H3···Cg3iii0.932.823.708 (3)160
C11—H11···Cg1iv0.932.893.683 (3)144
C17—H17A···Cg2v0.972.813.571 (3)136
C17—H17B···Cg30.972.903.810 (4)157
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) y+1, x+1, z+1; (iii) y+1, x1, z+1; (iv) y+1, x+1, z; (v) x, y, z1.

Experimental details

Crystal data
Chemical formulaC24H26FN3O
Mr391.48
Crystal system, space groupTetragonal, I4
Temperature (K)296
a, c (Å)22.6986 (11), 8.4480 (5)
V3)4352.6 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.63 × 0.46 × 0.28
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(Stoe & Cie, 2002)
Tmin, Tmax0.957, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
15640, 4531, 3430
Rint0.066
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.092, 1.03
No. of reflections4531
No. of parameters267
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.11

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the 1H-pyrrole (N1/C1/C6/C7/C14), benzene (C1–C6) and phenyl (C8–C13) rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.503.048 (4)123
N1—H1···N3i0.862.323.170 (3)168
C2—H2···O1i0.932.513.112 (4)123
C5—H5···F1ii0.932.523.383 (3)154
C3—H3···Cg3iii0.932.823.708 (3)160
C11—H11···Cg1iv0.932.893.683 (3)144
C17—H17A···Cg2v0.972.813.571 (3)136
C17—H17B···Cg30.972.903.810 (4)157
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) y+1, x+1, z+1; (iii) y+1, x1, z+1; (iv) y+1, x+1, z; (v) 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). This work was supported by the Scientific Research Projects Unit of İstanbul University (project No. T-471/25062004).

References

First citationAkkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830.  Web of Science CSD CrossRef IUCr Journals
First citationAkkurt, M., Zopun, M., Çapan, G. & Büyükgüngör, O. (2013). Acta Cryst. E69, o1137.  CSD CrossRef IUCr Journals
First citationCihan-Üstündağ, G. & Çapan, G. (2012). Mol. Divers. 16, 525–539.  Web of Science PubMed
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS 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.

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