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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Pages o1211-o1212

5-Fluoro-N′-(4-methyl­cyclo­hexyl­­idene)-3-phenyl-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 3 July 2013; online 6 July 2013)

The title compound, C22H22FN3O, crystallized with two independent mol­ecules (A and B) in the asymmetric unit; these are linked by a pair of N—H⋯O hydrogen bonds, forming a pseudo-centrosymmetric dimer with an R22(10) motif. In addition, a number of C—H⋯π inter­actions are also observed. The 1H-indole ring systems in mol­ecules A and B are essentially planar [maximum deviations of 0.019 (2) and 0.014 (2) Å, respectively] and make dihedral angles of 77.64 (10) and 69.50 (9)°, respectively, with thephenyl rings.

Related literature

For the synthesis and characterization of some bioactive indole derivatives, 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.]); Zhang et al. (2004[Zhang, H. Z., Drewe, J., Tseng, B., Kasibhatla, S. & Cai, S. X. (2004). Bioorg. Med. Chem. 12, 3649-3655.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C22H22FN3O

  • Mr = 363.43

  • Triclinic, [P \overline 1]

  • a = 11.6630 (6) Å

  • b = 13.5320 (7) Å

  • c = 14.7754 (8) Å

  • α = 112.967 (4)°

  • β = 95.936 (4)°

  • γ = 111.385 (4)°

  • V = 1915.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.68 × 0.52 × 0.33 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 = 0.948, Tmax = 0.972

  • 26097 measured reflections

  • 8702 independent reflections

  • 5714 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.144

  • S = 1.03

  • 8702 reflections

  • 496 parameters

  • 2 restraints

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

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg6 and Cg8 are the centroids of the 1H-pyrrole and benzene rings of the 1H-indole ring system of mol­ecule A, the phenyl ring of mol­ecule A, the 1H-pyrrole ring of the 1H-indole ring system of mol­ecule B and the phenyl ring of mol­ecule B, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2 0.86 2.15 2.895 (2) 145
N4—H4⋯O1 0.86 2.04 2.811 (2) 149
C17—H17ACg1i 0.97 2.66 3.594 (3) 163
C17—H17BCg3 0.97 2.74 3.685 (3) 164
C31—H31⋯Cg6ii 0.93 2.87 3.658 (2) 144
C35—H35⋯Cg2iii 0.93 2.96 3.627 (3) 130
C39—H39BCg8 0.97 2.72 3.667 (3) 164
C42—H42ACg1iv 0.97 2.99 3.848 (3) 148
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z.

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

Indole-2-carbohydrazides are attractive targets in organic synthesis because of the biological potential of the indole scaffold and the synthetic utility of the carbohydrazide function (Zhang et al., 2004; Akkurt et al., 2010; 2013). The title compound has been synthesized as a member of a series of indolylhydrazones with antituberculosis properties (Cihan-Üstündağ & Çapan, 2012). To fully characterize the structure, we now report on the X-ray diffraction analysis of the title compound.

In the title compound, (I), (Fig. 1), the asymmetric unit contains two crystallographically independent molecules, A and B, whose cyclohexane rings adopt distorted chair conformations [the puckering parameters (Cremer & Pople, 1975) are QT = 0.520 (3) Å, θ = 168.2 (3)°, ϕ = 31.9 (15)° for molecule A (with N1), and QT = 0.520 (3) Å, θ = 168.2 (3)°, ϕ = 31.9 (15)° for molecule B (with N4)].

The 1H-indole ring systems of both molecules A and B are essentially planar [maximum deviations are 0.019 (2) Å for C1 in molecule A and 0.014 (2) Å for C26 in molecule B]. The 1H-indole ring systems of molecules A and B make dihedral angles of 77.64 (10) and 69.50 (9)° with their phenyl rings, respectively. The C14–C15–N2–N3, C15–N2–N3–C16, C36–C37–N5–N6, C37–N5–N6–C38 torsion angles are 174.92 (18), -175.2 (2), -179.95 (17) and 178.4 (2)°, respectively.

In the crystal, the two molecules in the asymmetric unit are connected to each other, forming N—H···O dimers (Table 1, Fig. 2), giving rise to R22(10) ring patterns (Bernstein et al., 1995). Furthermore, C—H···π interactions (Table 1) contribute to the stability of the crystal packing in (I).

Related literature top

For the synthesis and characterization of some bioactive indole derivatives, see: Akkurt et al. (2010, 2013); Cihan-Üstündağ & Çapan (2012); Zhang et al. (2004). For puckering analysis, see: Cremer & Pople (1975). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

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

Yield:73%, mp.: 466.5–468.5 K. IR(KBr): υmax 3348, 3240 (N—H), 1652 (C=O) cm-1. 1H-NMR (DMSO-d6/500 MHz): δ 0.87 (d, 3H, J=5.3 Hz, 4-CH3-cyc.*), 1.00–1.14 (m, 1H, CH2-cyc.), 1.44–1.64 (br. m, 4H, CH, CH2-cyc.), 1.66–1.84 (m, 2H, CH2-cyc.), 2.15 (s, 1H, CH2-cyc.), 2.29 (s, 1H, CH2-cyc.), 7.12 (br. t, 2H, J=8.5 Hz, H4,H6-ind.), 7.33–7.50 (m, 6H, H7, 3-C6H5-ind.), 9.44 (s, 1H, CONH), 12.02 (s, 1H, NH) p.p.m.. Analysis calculated for C22H22FN3O: C 72.71, H 6.10, N 11.56%. Found: C 72.67, H 6.39, N 11.57%. (*cyc.=cyclohexylidene, ind.=indole).

Refinement top

H atoms bonded to C atoms and the H atoms (N1)H1 and (N4)H4 of the two of the four 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 atoms (N2)H2N and (N5)H5N of the two amide groups were found in a difference Fourier map and were refined freely. The crystal studied was a non-merohedral twin (twin law 0.24 0.00 - 0.75 - 0.09 - 1.00 0.05 - 1.26 0.00 - 0.24), with the minor twin component refining to 0.00116 (8).

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), showing the atom labelling scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the N—H···O dimer in the unit cell. H atoms not participating in hydrogen bonding have been omitted for clarity and hydrogen bonds are drawn as dashed lines.
5-Fluoro-N'-(4-methylcyclohexylidene)-3-phenyl-1H-indole-2-carbohydrazide top
Crystal data top
C22H22FN3OZ = 4
Mr = 363.43F(000) = 768
Triclinic, P1Dx = 1.260 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.6630 (6) ÅCell parameters from 35686 reflections
b = 13.5320 (7) Åθ = 2.0–28.0°
c = 14.7754 (8) ŵ = 0.09 mm1
α = 112.967 (4)°T = 296 K
β = 95.936 (4)°Prism, colourless
γ = 111.385 (4)°0.68 × 0.52 × 0.33 mm
V = 1915.4 (2) Å3
Data collection top
Stoe IPDS 2
diffractometer
8702 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus5714 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.058
Detector resolution: 6.67 pixels mm-1θmax = 27.6°, θmin = 2.0°
ω scansh = 1515
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1717
Tmin = 0.948, Tmax = 0.972l = 1919
26097 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144 W = 1/[Σ2(FO2) + (0.0744P)2 + 0.1246P] WHERE P = (FO2 + 2FC2)/3
S = 1.03(Δ/σ)max < 0.001
8702 reflectionsΔρmax = 0.42 e Å3
496 parametersΔρmin = 0.37 e Å3
Crystal data top
C22H22FN3Oγ = 111.385 (4)°
Mr = 363.43V = 1915.4 (2) Å3
Triclinic, P1Z = 4
a = 11.6630 (6) ÅMo Kα radiation
b = 13.5320 (7) ŵ = 0.09 mm1
c = 14.7754 (8) ÅT = 296 K
α = 112.967 (4)°0.68 × 0.52 × 0.33 mm
β = 95.936 (4)°
Data collection top
Stoe IPDS 2
diffractometer
8702 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
5714 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.972Rint = 0.058
26097 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0572 restraints
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.42 e Å3
8702 reflectionsΔρmin = 0.37 e Å3
496 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
F10.33494 (17)0.02996 (12)0.06230 (14)0.1113 (7)
O10.68124 (14)0.68746 (12)0.28626 (9)0.0679 (5)
N10.52435 (14)0.45358 (13)0.24287 (11)0.0543 (5)
N20.70784 (16)0.62496 (14)0.12738 (12)0.0547 (5)
N30.78349 (15)0.73959 (13)0.14306 (11)0.0564 (5)
C10.46778 (18)0.33259 (17)0.20839 (13)0.0553 (6)
C20.3836 (2)0.2633 (2)0.24439 (16)0.0669 (7)
C30.3400 (2)0.1422 (2)0.19316 (18)0.0771 (9)
C40.3792 (2)0.09106 (19)0.10798 (19)0.0761 (8)
C50.4602 (2)0.15512 (18)0.06997 (16)0.0678 (7)
C60.50520 (18)0.27986 (16)0.12087 (13)0.0547 (6)
C70.58613 (17)0.37471 (16)0.10276 (12)0.0510 (5)
C80.64165 (17)0.35989 (15)0.01471 (12)0.0495 (5)
C90.56439 (19)0.32276 (19)0.08081 (14)0.0640 (7)
C100.6149 (2)0.3174 (2)0.16231 (14)0.0724 (8)
C110.7423 (2)0.34579 (18)0.15024 (14)0.0685 (7)
C120.8187 (2)0.3774 (2)0.05808 (16)0.0773 (8)
C130.7693 (2)0.3848 (2)0.02451 (14)0.0689 (7)
C140.59506 (17)0.47922 (16)0.17903 (12)0.0501 (5)
C150.66499 (16)0.60585 (16)0.20329 (12)0.0499 (5)
C160.81127 (17)0.74851 (16)0.06423 (14)0.0546 (6)
C170.7672 (2)0.6516 (2)0.04384 (15)0.0716 (7)
C180.8715 (3)0.66082 (19)0.09684 (16)0.0813 (8)
C190.9486 (3)0.7848 (2)0.08349 (18)0.0837 (9)
C201.0026 (2)0.87295 (18)0.02981 (17)0.0725 (7)
C210.8962 (2)0.87190 (18)0.08106 (17)0.0705 (8)
C221.0472 (3)0.7915 (3)0.1398 (3)0.1207 (14)
F20.95169 (12)1.23386 (12)0.77835 (10)0.0893 (5)
O20.39600 (13)0.58695 (12)0.35468 (10)0.0678 (5)
N40.62682 (15)0.79327 (14)0.47138 (11)0.0576 (5)
N50.28375 (16)0.68606 (16)0.42914 (13)0.0627 (6)
N60.16405 (16)0.59508 (15)0.36881 (11)0.0648 (5)
C230.72321 (18)0.90083 (16)0.54295 (13)0.0535 (6)
C240.85522 (19)0.95099 (19)0.55570 (15)0.0632 (7)
C250.9302 (2)1.0619 (2)0.63591 (16)0.0674 (7)
C260.8732 (2)1.12177 (18)0.70176 (15)0.0645 (7)
C270.74541 (18)1.07482 (17)0.69316 (14)0.0589 (6)
C280.66725 (17)0.96119 (15)0.61105 (12)0.0506 (6)
C290.53239 (17)0.88540 (15)0.57767 (12)0.0501 (6)
C300.43961 (16)0.91430 (15)0.63207 (12)0.0498 (5)
C310.4100 (2)1.00510 (18)0.63397 (15)0.0653 (7)
C320.3272 (2)1.0345 (2)0.68837 (18)0.0777 (8)
C330.2746 (2)0.9750 (2)0.74062 (18)0.0849 (9)
C340.3030 (2)0.8843 (2)0.73919 (18)0.0847 (10)
C350.3847 (2)0.85356 (19)0.68489 (15)0.0659 (7)
C360.51112 (17)0.78338 (16)0.49088 (12)0.0513 (6)
C370.39356 (18)0.67621 (16)0.41905 (13)0.0541 (6)
C380.06794 (19)0.61469 (18)0.38764 (14)0.0626 (6)
C390.0688 (2)0.7241 (2)0.46963 (18)0.0765 (8)
C400.0321 (2)0.6933 (2)0.52374 (18)0.0854 (9)
C410.1642 (2)0.6026 (2)0.45358 (19)0.0816 (10)
C420.1578 (2)0.4916 (2)0.3791 (2)0.0907 (10)
C430.0627 (2)0.5196 (2)0.31960 (18)0.0865 (9)
C440.2606 (3)0.5777 (4)0.5126 (3)0.1196 (16)
H10.517000.505300.295800.0650*
H20.358100.298600.301300.0800*
H2N0.688 (2)0.563 (2)0.0781 (14)0.068 (6)*
H30.283800.093600.215200.0920*
H50.484500.118100.013000.0810*
H90.477000.301000.090400.0770*
H100.561900.294500.225500.0870*
H110.776600.343500.204700.0820*
H120.904900.394200.050300.0930*
H130.822800.406700.087100.0830*
H17A0.697100.654300.082700.0860*
H17B0.734100.574700.043600.0860*
H18A0.929200.635600.070300.0980*
H18B0.832700.606200.169500.0980*
H190.888000.806300.113100.1000*
H20A1.051700.952800.038100.0870*
H20B1.060300.852500.062900.0870*
H21A0.933900.924900.154100.0850*
H21B0.844700.901800.053700.0850*
H22A1.109300.771900.112600.1450*
H22B1.089400.871200.132100.1450*
H22C1.006600.735900.211300.1450*
H40.636700.739800.421700.0690*
H5N0.2992 (17)0.750 (2)0.4704 (16)0.067 (6)*
H240.891200.910000.510800.0760*
H251.018601.097500.646700.0810*
H270.711401.116400.739800.0710*
H310.445701.046700.598700.0780*
H320.307601.095400.689000.0930*
H330.219600.995500.777200.1020*
H340.267000.843400.774900.1020*
H350.402900.791700.683900.0790*
H39A0.053500.771600.439100.0920*
H39B0.153000.772200.519600.0920*
H40A0.004900.663100.567400.1020*
H40B0.036700.766000.567700.1020*
H410.191800.636900.413200.0980*
H42A0.242400.435200.331400.1090*
H42B0.132900.454200.416600.1090*
H43A0.056100.447300.277600.1040*
H43B0.094900.545400.274100.1040*
H44A0.264200.650700.555000.1440*
H44B0.234900.546400.554900.1440*
H44C0.343900.520300.465200.1440*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1200 (13)0.0613 (8)0.1456 (14)0.0303 (9)0.0534 (11)0.0465 (9)
O10.0915 (10)0.0593 (8)0.0553 (7)0.0372 (8)0.0418 (7)0.0201 (6)
N10.0650 (10)0.0590 (9)0.0493 (7)0.0337 (8)0.0316 (7)0.0251 (7)
N20.0649 (10)0.0471 (8)0.0495 (8)0.0234 (8)0.0289 (7)0.0182 (7)
N30.0590 (9)0.0512 (8)0.0618 (8)0.0266 (8)0.0326 (7)0.0230 (7)
C10.0599 (11)0.0630 (11)0.0557 (9)0.0329 (10)0.0258 (8)0.0317 (9)
C20.0704 (13)0.0824 (14)0.0676 (11)0.0383 (12)0.0347 (10)0.0452 (11)
C30.0762 (15)0.0790 (15)0.0914 (15)0.0298 (13)0.0344 (12)0.0554 (13)
C40.0800 (15)0.0568 (12)0.0924 (15)0.0273 (12)0.0287 (12)0.0370 (11)
C50.0749 (14)0.0607 (12)0.0730 (12)0.0350 (11)0.0308 (11)0.0288 (10)
C60.0586 (11)0.0575 (10)0.0565 (9)0.0314 (9)0.0247 (8)0.0270 (8)
C70.0552 (10)0.0563 (10)0.0493 (8)0.0309 (9)0.0241 (8)0.0237 (8)
C80.0573 (10)0.0481 (9)0.0465 (8)0.0288 (8)0.0238 (8)0.0177 (7)
C90.0580 (11)0.0761 (13)0.0534 (10)0.0312 (11)0.0201 (9)0.0232 (9)
C100.0820 (15)0.0837 (15)0.0470 (9)0.0384 (13)0.0228 (10)0.0234 (10)
C110.0844 (15)0.0646 (12)0.0539 (10)0.0337 (11)0.0386 (10)0.0196 (9)
C120.0593 (12)0.0933 (16)0.0709 (13)0.0368 (12)0.0342 (11)0.0236 (11)
C130.0608 (12)0.0920 (15)0.0512 (9)0.0410 (12)0.0212 (9)0.0226 (10)
C140.0550 (10)0.0583 (10)0.0462 (8)0.0304 (9)0.0254 (7)0.0252 (8)
C150.0528 (10)0.0581 (10)0.0469 (8)0.0320 (9)0.0251 (7)0.0224 (8)
C160.0539 (10)0.0545 (10)0.0623 (10)0.0273 (9)0.0282 (8)0.0275 (8)
C170.0747 (14)0.0708 (13)0.0549 (10)0.0169 (11)0.0197 (10)0.0295 (10)
C180.1014 (18)0.0663 (13)0.0631 (12)0.0262 (13)0.0425 (12)0.0231 (10)
C190.1068 (18)0.0744 (14)0.0788 (14)0.0367 (14)0.0553 (14)0.0397 (12)
C200.0766 (14)0.0552 (11)0.0834 (13)0.0224 (11)0.0436 (12)0.0310 (10)
C210.0832 (15)0.0560 (11)0.0819 (13)0.0344 (11)0.0445 (12)0.0323 (10)
C220.166 (3)0.0908 (19)0.130 (2)0.058 (2)0.108 (2)0.0568 (18)
F20.0637 (8)0.0726 (8)0.0934 (9)0.0224 (7)0.0195 (7)0.0107 (7)
O20.0712 (9)0.0612 (8)0.0633 (7)0.0334 (7)0.0345 (7)0.0141 (6)
N40.0643 (10)0.0611 (9)0.0542 (8)0.0353 (8)0.0347 (7)0.0217 (7)
N50.0600 (10)0.0581 (10)0.0574 (9)0.0282 (9)0.0224 (8)0.0115 (8)
N60.0615 (10)0.0671 (10)0.0511 (8)0.0295 (9)0.0185 (7)0.0121 (7)
C230.0591 (11)0.0580 (10)0.0523 (9)0.0303 (9)0.0301 (8)0.0262 (8)
C240.0627 (12)0.0732 (13)0.0670 (11)0.0391 (11)0.0382 (10)0.0316 (10)
C250.0560 (12)0.0743 (13)0.0743 (12)0.0296 (11)0.0304 (10)0.0330 (11)
C260.0613 (12)0.0613 (12)0.0624 (11)0.0250 (10)0.0218 (9)0.0217 (9)
C270.0628 (12)0.0591 (11)0.0564 (9)0.0312 (10)0.0289 (9)0.0215 (9)
C280.0562 (10)0.0550 (10)0.0517 (9)0.0301 (9)0.0297 (8)0.0263 (8)
C290.0571 (11)0.0533 (10)0.0488 (8)0.0282 (9)0.0280 (8)0.0252 (8)
C300.0526 (10)0.0512 (9)0.0438 (8)0.0249 (8)0.0232 (7)0.0161 (7)
C310.0738 (13)0.0611 (11)0.0727 (12)0.0370 (11)0.0381 (10)0.0310 (10)
C320.0784 (15)0.0675 (13)0.0924 (15)0.0461 (12)0.0401 (13)0.0251 (12)
C330.0807 (15)0.0965 (17)0.0811 (14)0.0510 (14)0.0527 (13)0.0262 (13)
C340.0865 (16)0.1159 (19)0.0835 (14)0.0558 (15)0.0595 (13)0.0568 (14)
C350.0705 (13)0.0786 (13)0.0714 (12)0.0408 (11)0.0435 (10)0.0429 (11)
C360.0591 (11)0.0551 (10)0.0486 (8)0.0303 (9)0.0306 (8)0.0239 (8)
C370.0636 (11)0.0583 (10)0.0485 (8)0.0317 (9)0.0310 (8)0.0241 (8)
C380.0644 (12)0.0696 (12)0.0514 (9)0.0327 (11)0.0206 (9)0.0218 (9)
C390.0735 (14)0.0701 (14)0.0823 (14)0.0390 (12)0.0305 (12)0.0231 (11)
C400.0867 (17)0.1039 (18)0.0774 (14)0.0603 (16)0.0352 (13)0.0333 (13)
C410.0775 (16)0.1055 (19)0.0903 (15)0.0522 (15)0.0395 (13)0.0573 (14)
C420.0626 (14)0.0847 (17)0.1170 (19)0.0308 (13)0.0188 (13)0.0428 (15)
C430.0684 (15)0.0888 (17)0.0716 (13)0.0378 (13)0.0089 (11)0.0084 (12)
C440.104 (2)0.174 (3)0.144 (3)0.077 (2)0.073 (2)0.109 (3)
Geometric parameters (Å, º) top
F1—C41.361 (3)C18—H18B0.9700
F2—C261.361 (3)C19—H190.9800
O1—C151.225 (2)C20—H20B0.9700
O2—C371.224 (2)C20—H20A0.9700
N1—C11.366 (3)C21—H21B0.9700
N1—C141.378 (3)C21—H21A0.9700
N2—C151.350 (3)C22—H22A0.9600
N2—N31.385 (3)C22—H22B0.9600
N3—C161.279 (3)C22—H22C0.9600
N1—H10.8600C23—C241.395 (3)
N2—H2N0.80 (2)C23—C281.410 (3)
N4—C361.379 (3)C24—C251.365 (3)
N4—C231.364 (3)C25—C261.399 (3)
N5—N61.376 (3)C26—C271.360 (3)
N5—C371.352 (3)C27—C281.400 (3)
N6—C381.276 (3)C28—C291.427 (3)
N4—H40.8600C29—C301.488 (3)
N5—H5N0.78 (2)C29—C361.384 (3)
C1—C61.413 (3)C30—C311.384 (3)
C1—C21.397 (3)C30—C351.384 (3)
C2—C31.364 (4)C31—C321.389 (3)
C3—C41.394 (3)C32—C331.358 (4)
C4—C51.361 (4)C33—C341.376 (4)
C5—C61.404 (3)C34—C351.383 (3)
C6—C71.431 (3)C36—C371.469 (3)
C7—C81.489 (3)C38—C431.494 (3)
C7—C141.380 (3)C38—C391.499 (3)
C8—C91.382 (3)C39—C401.515 (4)
C8—C131.379 (3)C40—C411.501 (4)
C9—C101.383 (3)C41—C421.511 (4)
C10—C111.365 (4)C41—C441.515 (5)
C11—C121.359 (3)C42—C431.517 (4)
C12—C131.387 (3)C24—H240.9300
C14—C151.473 (3)C25—H250.9300
C16—C211.500 (3)C27—H270.9300
C16—C171.496 (3)C31—H310.9300
C17—C181.507 (4)C32—H320.9300
C18—C191.506 (4)C33—H330.9300
C19—C221.485 (5)C34—H340.9300
C19—C201.516 (3)C35—H350.9300
C20—C211.518 (3)C39—H39A0.9700
C2—H20.9300C39—H39B0.9700
C3—H30.9300C40—H40A0.9700
C5—H50.9300C40—H40B0.9700
C9—H90.9300C41—H410.9800
C10—H100.9300C42—H42A0.9700
C11—H110.9300C42—H42B0.9700
C12—H120.9300C43—H43A0.9700
C13—H130.9300C43—H43B0.9700
C17—H17B0.9700C44—H44A0.9600
C17—H17A0.9700C44—H44B0.9600
C18—H18A0.9700C44—H44C0.9600
C1—N1—C14108.92 (16)H21A—C21—H21B108.00
N3—N2—C15120.98 (16)C19—C22—H22A110.00
N2—N3—C16115.91 (16)C19—C22—H22B109.00
C1—N1—H1126.00H22A—C22—H22C110.00
C14—N1—H1126.00C19—C22—H22C109.00
N3—N2—H2N128.4 (19)H22A—C22—H22B109.00
C15—N2—H2N110.5 (18)H22B—C22—H22C109.00
C23—N4—C36109.59 (16)N4—C23—C24130.90 (19)
N6—N5—C37122.72 (18)N4—C23—C28107.45 (19)
N5—N6—C38116.56 (18)C24—C23—C28121.65 (18)
C36—N4—H4125.00C23—C24—C25118.2 (2)
C23—N4—H4125.00C24—C25—C26119.6 (2)
C37—N5—H5N110.4 (17)F2—C26—C27118.9 (2)
N6—N5—H5N126.8 (17)C25—C26—C27123.9 (2)
N1—C1—C6107.95 (18)F2—C26—C25117.2 (2)
N1—C1—C2130.44 (19)C26—C27—C28117.09 (19)
C2—C1—C6121.6 (2)C27—C28—C29132.93 (19)
C1—C2—C3117.7 (2)C23—C28—C29107.56 (16)
C2—C3—C4120.3 (2)C23—C28—C27119.52 (19)
F1—C4—C3117.2 (2)C28—C29—C36106.29 (18)
F1—C4—C5118.9 (2)C30—C29—C36129.37 (19)
C3—C4—C5123.9 (2)C28—C29—C30124.30 (16)
C4—C5—C6116.8 (2)C29—C30—C31120.77 (18)
C5—C6—C7133.18 (19)C29—C30—C35120.51 (19)
C1—C6—C5119.7 (2)C31—C30—C35118.7 (2)
C1—C6—C7107.12 (18)C30—C31—C32120.3 (2)
C6—C7—C8125.71 (17)C31—C32—C33120.6 (2)
C8—C7—C14127.95 (19)C32—C33—C34119.7 (2)
C6—C7—C14106.25 (17)C33—C34—C35120.4 (2)
C7—C8—C13122.73 (16)C30—C35—C34120.4 (2)
C9—C8—C13117.73 (18)N4—C36—C29109.11 (17)
C7—C8—C9119.52 (19)N4—C36—C37118.25 (16)
C8—C9—C10121.1 (2)C29—C36—C37132.6 (2)
C9—C10—C11120.20 (19)N5—C37—C36114.19 (18)
C10—C11—C12119.6 (2)O2—C37—N5123.4 (2)
C11—C12—C13120.6 (2)O2—C37—C36122.4 (2)
C8—C13—C12120.69 (19)N6—C38—C43117.47 (19)
N1—C14—C7109.76 (18)C39—C38—C43114.5 (2)
N1—C14—C15117.64 (16)N6—C38—C39128.0 (2)
C7—C14—C15132.59 (18)C38—C39—C40112.2 (2)
O1—C15—C14121.94 (17)C39—C40—C41114.7 (2)
N2—C15—C14115.28 (16)C40—C41—C42109.5 (2)
O1—C15—N2122.8 (2)C42—C41—C44113.5 (3)
N3—C16—C21116.31 (18)C40—C41—C44111.9 (2)
C17—C16—C21115.47 (19)C41—C42—C43112.0 (2)
N3—C16—C17128.2 (2)C38—C43—C42112.8 (2)
C16—C17—C18113.6 (2)C23—C24—H24121.00
C17—C18—C19113.8 (2)C25—C24—H24121.00
C18—C19—C22113.2 (3)C24—C25—H25120.00
C20—C19—C22113.5 (3)C26—C25—H25120.00
C18—C19—C20109.6 (2)C26—C27—H27121.00
C19—C20—C21111.3 (2)C28—C27—H27121.00
C16—C21—C20111.7 (2)C30—C31—H31120.00
C3—C2—H2121.00C32—C31—H31120.00
C1—C2—H2121.00C31—C32—H32120.00
C4—C3—H3120.00C33—C32—H32120.00
C2—C3—H3120.00C32—C33—H33120.00
C6—C5—H5122.00C34—C33—H33120.00
C4—C5—H5122.00C33—C34—H34120.00
C8—C9—H9119.00C35—C34—H34120.00
C10—C9—H9119.00C30—C35—H35120.00
C9—C10—H10120.00C34—C35—H35120.00
C11—C10—H10120.00C38—C39—H39A109.00
C12—C11—H11120.00C38—C39—H39B109.00
C10—C11—H11120.00C40—C39—H39A109.00
C13—C12—H12120.00C40—C39—H39B109.00
C11—C12—H12120.00H39A—C39—H39B108.00
C12—C13—H13120.00C39—C40—H40A109.00
C8—C13—H13120.00C39—C40—H40B109.00
C18—C17—H17A109.00C41—C40—H40A109.00
H17A—C17—H17B108.00C41—C40—H40B109.00
C16—C17—H17B109.00H40A—C40—H40B108.00
C18—C17—H17B109.00C40—C41—H41107.00
C16—C17—H17A109.00C42—C41—H41107.00
C17—C18—H18A109.00C44—C41—H41107.00
C17—C18—H18B109.00C41—C42—H42A109.00
C19—C18—H18A109.00C41—C42—H42B109.00
H18A—C18—H18B108.00C43—C42—H42A109.00
C19—C18—H18B109.00C43—C42—H42B109.00
C20—C19—H19107.00H42A—C42—H42B108.00
C18—C19—H19107.00C38—C43—H43A109.00
C22—C19—H19107.00C38—C43—H43B109.00
H20A—C20—H20B108.00C42—C43—H43A109.00
C19—C20—H20A109.00C42—C43—H43B109.00
C19—C20—H20B109.00H43A—C43—H43B108.00
C21—C20—H20A109.00C41—C44—H44A109.00
C21—C20—H20B109.00C41—C44—H44B110.00
C16—C21—H21A109.00C41—C44—H44C109.00
C16—C21—H21B109.00H44A—C44—H44B110.00
C20—C21—H21A109.00H44A—C44—H44C109.00
C20—C21—H21B109.00H44B—C44—H44C109.00
C1—N1—C14—C15179.61 (17)C17—C16—C21—C2047.1 (3)
C14—N1—C1—C2177.1 (2)N3—C16—C17—C18138.7 (3)
C14—N1—C1—C60.9 (2)C21—C16—C17—C1842.9 (3)
C1—N1—C14—C70.6 (2)C16—C17—C18—C1946.9 (3)
C15—N2—N3—C16175.2 (2)C17—C18—C19—C22177.5 (2)
N3—N2—C15—O16.0 (3)C17—C18—C19—C2054.7 (3)
N3—N2—C15—C14174.92 (18)C18—C19—C20—C2158.6 (3)
N2—N3—C16—C21178.36 (19)C22—C19—C20—C21173.7 (3)
N2—N3—C16—C173.3 (3)C19—C20—C21—C1655.0 (3)
C23—N4—C36—C37176.82 (18)C24—C23—C28—C29179.1 (2)
C23—N4—C36—C291.0 (2)N4—C23—C24—C25179.6 (2)
C36—N4—C23—C280.6 (2)C28—C23—C24—C250.7 (3)
C36—N4—C23—C24179.6 (2)N4—C23—C28—C290.0 (2)
C37—N5—N6—C38178.4 (2)C24—C23—C28—C270.6 (3)
N6—N5—C37—O21.3 (3)N4—C23—C28—C27179.71 (18)
N6—N5—C37—C36179.95 (17)C23—C24—C25—C260.5 (4)
N5—N6—C38—C391.7 (3)C24—C25—C26—F2177.7 (2)
N5—N6—C38—C43176.9 (2)C24—C25—C26—C272.0 (4)
C2—C1—C6—C51.9 (3)C25—C26—C27—C282.1 (3)
N1—C1—C6—C5179.92 (19)F2—C26—C27—C28177.62 (19)
N1—C1—C2—C3178.9 (2)C26—C27—C28—C29179.6 (2)
C6—C1—C2—C31.2 (3)C26—C27—C28—C230.8 (3)
C2—C1—C6—C7177.4 (2)C27—C28—C29—C302.5 (4)
N1—C1—C6—C70.8 (2)C23—C28—C29—C360.6 (2)
C1—C2—C3—C40.0 (4)C27—C28—C29—C36179.8 (2)
C2—C3—C4—C50.5 (4)C23—C28—C29—C30177.10 (18)
C2—C3—C4—F1178.2 (2)C28—C29—C36—N41.0 (2)
C3—C4—C5—C60.2 (4)C28—C29—C30—C3169.5 (3)
F1—C4—C5—C6178.8 (2)C28—C29—C36—C37176.4 (2)
C4—C5—C6—C11.3 (3)C30—C29—C36—N4176.60 (19)
C4—C5—C6—C7177.8 (2)C36—C29—C30—C3569.0 (3)
C5—C6—C7—C82.9 (4)C36—C29—C30—C31113.3 (2)
C5—C6—C7—C14179.6 (2)C30—C29—C36—C376.1 (4)
C1—C6—C7—C8176.27 (19)C28—C29—C30—C35108.2 (2)
C1—C6—C7—C140.4 (2)C31—C30—C35—C340.7 (3)
C6—C7—C8—C13105.2 (3)C29—C30—C35—C34177.08 (19)
C14—C7—C8—C1378.9 (3)C29—C30—C31—C32177.44 (19)
C6—C7—C14—C15178.9 (2)C35—C30—C31—C320.3 (3)
C6—C7—C14—N10.1 (2)C30—C31—C32—C330.2 (3)
C6—C7—C8—C976.6 (3)C31—C32—C33—C340.4 (4)
C8—C7—C14—C154.5 (4)C32—C33—C34—C350.0 (4)
C14—C7—C8—C999.4 (3)C33—C34—C35—C300.5 (3)
C8—C7—C14—N1176.70 (19)N4—C36—C37—N5164.94 (19)
C9—C8—C13—C122.6 (4)C29—C36—C37—O2169.0 (2)
C7—C8—C13—C12175.6 (2)C29—C36—C37—N512.2 (3)
C7—C8—C9—C10174.7 (2)N4—C36—C37—O213.8 (3)
C13—C8—C9—C103.7 (4)N6—C38—C39—C40136.0 (2)
C8—C9—C10—C111.8 (4)C43—C38—C39—C4045.4 (3)
C9—C10—C11—C121.1 (4)N6—C38—C43—C42132.9 (2)
C10—C11—C12—C132.1 (4)C39—C38—C43—C4248.3 (3)
C11—C12—C13—C80.2 (4)C38—C39—C40—C4149.3 (3)
N1—C14—C15—O113.7 (3)C39—C40—C41—C4254.3 (3)
C7—C14—C15—N215.9 (3)C39—C40—C41—C44179.0 (3)
C7—C14—C15—O1165.0 (2)C40—C41—C42—C4355.5 (3)
N1—C14—C15—N2165.41 (18)C44—C41—C42—C43178.6 (2)
N3—C16—C21—C20134.3 (2)C41—C42—C43—C3853.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3, Cg6 and Cg8 are the centroids of the 1H-pyrrole and benzene rings of the 1H-indole ring system of molecule A, the phenyl ring of molecule A, the 1H-pyrrole ring of the 1H-indole ring system of molecule B and the phenyl ring of molecule B, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.152.895 (2)145
N4—H4···O10.862.042.811 (2)149
C17—H17B···N20.972.432.811 (3)103
C39—H39B···N50.972.442.814 (3)102
C17—H17A···Cg1i0.972.663.594 (3)163
C17—H17B···Cg30.972.743.685 (3)164
C31—H31···Cg6ii0.932.873.658 (2)144
C35—H35···Cg2iii0.932.963.627 (3)130
C39—H39B···Cg80.972.723.667 (3)164
C42—H42A···Cg1iv0.972.993.848 (3)148
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1; (iv) x1, y, z.

Experimental details

Crystal data
Chemical formulaC22H22FN3O
Mr363.43
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)11.6630 (6), 13.5320 (7), 14.7754 (8)
α, β, γ (°)112.967 (4), 95.936 (4), 111.385 (4)
V3)1915.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.68 × 0.52 × 0.33
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.948, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
26097, 8702, 5714
Rint0.058
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.144, 1.03
No. of reflections8702
No. of parameters496
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.37

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, Cg3, Cg6 and Cg8 are the centroids of the 1H-pyrrole and benzene rings of the 1H-indole ring system of molecule A, the phenyl ring of molecule A, the 1H-pyrrole ring of the 1H-indole ring system of molecule B and the phenyl ring of molecule B, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.152.895 (2)145
N4—H4···O10.862.042.811 (2)149
C17—H17A···Cg1i0.972.663.594 (3)163
C17—H17B···Cg30.972.743.685 (3)164
C31—H31···Cg6ii0.932.873.658 (2)144
C35—H35···Cg2iii0.932.963.627 (3)130
C39—H39B···Cg80.972.723.667 (3)164
C42—H42A···Cg1iv0.972.993.848 (3)148
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1; (iv) x1, y, z.
 

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 Coordination Unit of İstanbul University (project No. T-471/25062004)

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Volume 69| Part 8| August 2013| Pages o1211-o1212
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