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

Çelikesir, S.T.; Akkurt, M.; Üstündağ, G.C.; Büyükgüngör, O.

doi:10.1107/S1600536813018333

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1202

doi:10.1107/S1600536813018333

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

Sevim Türktekin Çelikesir,^a Mehmet Akkurt,^a ^* Gökçe Cihan Üstündağ ^b and Orhan Büyükgüngör ^c

^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 , 2013 ); Cihan-Üstündağ & Çapan (2012 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₆FN₃O
M_r = 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 ) T_min = 0.957, T_max = 0.978
15640 measured reflections
4531 independent reflections
3430 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.13 e Å⁻³
Δρ_min = −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	D⋯A	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⋯Cg1^iv	0.93	2.89	3.683 (3)	144
C17—H17A⋯Cg2^v	0.97	2.81	3.571 (3)	136
C17—H17B⋯Cg3	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); cell refinement: X-AREA; 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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018333/hb7101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018333/hb7101Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018333/hb7101Isup3.cml

checkCIF report

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): υ_max 3366, 3243 (N—H), 1690 (C=O) cm^{-1. 1}H-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).

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

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	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

C₂₄H₂₆FN₃O	D_x = 1.195 Mg m⁻³
M_r = 391.48	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 20884 reflections
Hall symbol: I -4	θ = 2.5–27.4°
a = 22.6986 (11) Å	µ = 0.08 mm⁻¹
c = 8.4480 (5) Å	T = 296 K
V = 4352.6 (5) Å³	Prism, colourless
Z = 8	0.63 × 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 focus	3430 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.066
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.5°
ω–scans	h = −28→27
Absorption correction: integration (Stoe & Cie, 2002)	k = −28→28
T_min = 0.957, T_max = 0.978	l = −10→10
15640 measured reflections

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.047	H 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 reflections	Δρ_max = 0.13 e Å⁻³
267 parameters	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₂₄H₂₆FN₃O	Z = 8
M_r = 391.48	Mo Kα radiation
Tetragonal, I4	µ = 0.08 mm⁻¹
a = 22.6986 (11) Å	T = 296 K
c = 8.4480 (5) Å	0.63 × 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)
T_min = 0.957, T_max = 0.978	R_int = 0.066
15640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.13 e Å⁻³
4531 reflections	Δρ_min = −0.11 e Å⁻³
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

	x	y	z	U_iso*/U_eq
F1	0.95641 (9)	0.05822 (8)	0.6774 (3)	0.0742 (7)
O1	0.77085 (10)	0.26762 (14)	0.0944 (4)	0.1013 (11)
N1	0.80598 (10)	0.18855 (10)	0.3230 (3)	0.0513 (8)
N2	0.84810 (11)	0.24602 (12)	−0.0590 (3)	0.0588 (9)
N3	0.83121 (11)	0.28546 (12)	−0.1750 (3)	0.0608 (9)
C1	0.83656 (11)	0.15385 (12)	0.4270 (4)	0.0476 (9)
C2	0.82036 (14)	0.13032 (13)	0.5733 (4)	0.0587 (10)
C3	0.86172 (14)	0.09835 (13)	0.6542 (4)	0.0605 (11)
C4	0.91761 (14)	0.09077 (12)	0.5911 (4)	0.0559 (10)
C5	0.93519 (12)	0.11312 (12)	0.4498 (4)	0.0507 (9)
C6	0.89358 (11)	0.14621 (11)	0.3643 (3)	0.0432 (8)
C7	0.89623 (11)	0.17781 (11)	0.2192 (3)	0.0428 (8)
C8	0.94986 (11)	0.18498 (11)	0.1185 (3)	0.0443 (9)
C9	0.96716 (13)	0.14270 (14)	0.0110 (4)	0.0584 (11)
C10	1.01697 (14)	0.15077 (16)	−0.0816 (4)	0.0665 (11)
C11	1.05025 (13)	0.20044 (16)	−0.0662 (4)	0.0667 (11)
C12	1.03435 (15)	0.24189 (17)	0.0407 (5)	0.0777 (14)
C13	0.98449 (13)	0.23467 (14)	0.1336 (4)	0.0634 (11)
C14	0.84140 (11)	0.20304 (11)	0.1986 (3)	0.0465 (9)
C15	0.81674 (12)	0.24211 (14)	0.0752 (4)	0.0566 (10)
C16	0.86492 (14)	0.29068 (14)	−0.2948 (4)	0.0592 (11)
C17	0.92192 (15)	0.26047 (14)	−0.3283 (4)	0.0687 (11)
C18	0.97104 (15)	0.30538 (16)	−0.3529 (4)	0.0723 (12)
C19	0.95600 (16)	0.35201 (15)	−0.4750 (4)	0.0673 (11)
C20	0.89727 (17)	0.38012 (17)	−0.4386 (5)	0.0780 (12)
C21	0.84788 (16)	0.33486 (19)	−0.4175 (5)	0.0830 (14)
C22	1.0046 (2)	0.3974 (2)	−0.4948 (5)	0.0937 (16)
C23	1.0627 (2)	0.3747 (3)	−0.5558 (8)	0.131 (3)
C24	1.1078 (3)	0.4215 (4)	−0.5818 (8)	0.169 (4)
H1	0.77000	0.19950	0.33440	0.0620*
H2	0.78280	0.13620	0.61440	0.0700*
H2A	0.8751 (11)	0.2227 (12)	−0.060 (3)	0.060 (9)*
H3	0.85230	0.08170	0.75150	0.0730*
H5	0.97300	0.10680	0.41120	0.0610*
H9	0.94520	0.10830	0.00050	0.0700*
H10	1.02770	0.12210	−0.15470	0.0800*
H11	1.08360	0.20580	−0.12860	0.0800*
H12	1.05710	0.27570	0.05200	0.0930*
H13	0.97430	0.26350	0.20680	0.0760*
H17A	0.91790	0.23630	−0.42240	0.0830*
H17B	0.93190	0.23480	−0.24040	0.0830*
H18A	0.97950	0.32450	−0.25280	0.0870*
H18B	1.00640	0.28490	−0.38620	0.0870*
H19	0.95180	0.33180	−0.57680	0.0810*
H20A	0.88690	0.40670	−0.52400	0.0930*
H20B	0.90080	0.40320	−0.34250	0.0930*
H21A	0.81190	0.35470	−0.38560	0.1000*
H21B	0.84050	0.31500	−0.51730	0.1000*
H22A	0.99070	0.42770	−0.56670	0.1130*
H22B	1.01140	0.41600	−0.39310	0.1130*
H23A	1.07820	0.34630	−0.48090	0.1570*
H23B	1.05600	0.35430	−0.65500	0.1570*
H24A	1.11610	0.44090	−0.48330	0.2030*
H24B	1.09310	0.44970	−0.65680	0.2030*
H24C	1.14330	0.40400	−0.62200	0.2030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0820 (13)	0.0652 (11)	0.0755 (13)	0.0059 (9)	−0.0167 (10)	0.0183 (10)
O1	0.0639 (15)	0.135 (2)	0.105 (2)	0.0507 (15)	0.0263 (15)	0.0539 (19)
N1	0.0347 (11)	0.0569 (14)	0.0623 (15)	0.0076 (10)	0.0116 (11)	0.0062 (12)
N2	0.0488 (14)	0.0670 (16)	0.0605 (16)	0.0165 (13)	−0.0026 (13)	0.0149 (14)
N3	0.0486 (13)	0.0740 (17)	0.0599 (16)	0.0073 (12)	−0.0061 (14)	0.0195 (14)
C1	0.0434 (14)	0.0435 (14)	0.0558 (17)	0.0010 (11)	0.0067 (14)	−0.0004 (14)
C2	0.0553 (17)	0.0578 (17)	0.0630 (19)	0.0022 (14)	0.0196 (16)	0.0060 (16)
C3	0.074 (2)	0.0535 (17)	0.0540 (18)	−0.0014 (15)	0.0104 (17)	0.0073 (15)
C4	0.0631 (19)	0.0438 (16)	0.0609 (19)	0.0019 (13)	−0.0076 (16)	0.0050 (15)
C5	0.0426 (14)	0.0480 (15)	0.0616 (18)	0.0028 (12)	−0.0002 (14)	0.0011 (14)
C6	0.0405 (14)	0.0390 (13)	0.0502 (15)	0.0013 (11)	0.0035 (12)	−0.0029 (12)
C7	0.0364 (13)	0.0437 (14)	0.0483 (16)	0.0026 (11)	0.0025 (12)	−0.0005 (12)
C8	0.0336 (13)	0.0507 (15)	0.0487 (17)	0.0053 (11)	−0.0003 (12)	0.0087 (13)
C9	0.0444 (16)	0.0658 (19)	0.065 (2)	−0.0009 (14)	0.0054 (15)	−0.0084 (16)
C10	0.0536 (18)	0.084 (2)	0.062 (2)	0.0113 (16)	0.0098 (16)	−0.0081 (18)
C11	0.0432 (16)	0.087 (2)	0.070 (2)	0.0038 (16)	0.0174 (16)	0.014 (2)
C12	0.060 (2)	0.066 (2)	0.107 (3)	−0.0134 (17)	0.020 (2)	0.013 (2)
C13	0.0551 (18)	0.0540 (17)	0.081 (2)	−0.0016 (14)	0.0174 (17)	−0.0034 (16)
C14	0.0390 (14)	0.0482 (15)	0.0523 (16)	0.0023 (12)	0.0038 (13)	0.0020 (13)
C15	0.0379 (14)	0.0648 (18)	0.067 (2)	0.0075 (13)	0.0065 (15)	0.0128 (16)
C16	0.0519 (17)	0.0660 (19)	0.0596 (19)	−0.0019 (15)	−0.0097 (16)	0.0107 (16)
C17	0.078 (2)	0.0631 (19)	0.065 (2)	0.0053 (16)	0.0121 (18)	0.0046 (18)
C18	0.060 (2)	0.088 (2)	0.069 (2)	0.0106 (17)	0.0040 (18)	0.015 (2)
C19	0.070 (2)	0.075 (2)	0.0570 (19)	−0.0035 (17)	0.0010 (16)	0.0060 (17)
C20	0.085 (2)	0.079 (2)	0.070 (2)	0.0109 (19)	0.002 (2)	0.024 (2)
C21	0.064 (2)	0.109 (3)	0.076 (2)	0.0032 (19)	−0.0066 (19)	0.034 (2)
C22	0.095 (3)	0.109 (3)	0.077 (2)	−0.022 (2)	−0.005 (2)	0.022 (2)
C23	0.084 (3)	0.169 (5)	0.139 (5)	−0.026 (3)	0.007 (3)	0.047 (4)
C24	0.113 (4)	0.272 (9)	0.122 (5)	−0.080 (5)	−0.013 (4)	0.074 (5)

Geometric parameters (Å, º) top

F1—C4	1.361 (4)	C19—C22	1.519 (6)
O1—C15	1.203 (4)	C19—C20	1.510 (5)
N1—C1	1.369 (4)	C20—C21	1.531 (6)
N1—C14	1.364 (4)	C22—C23	1.507 (7)
N2—N3	1.382 (4)	C23—C24	1.492 (10)
N2—C15	1.342 (4)	C2—H2	0.9300
N3—C16	1.274 (4)	C3—H3	0.9300
N1—H1	0.8600	C5—H5	0.9300
N2—H2A	0.81 (3)	C9—H9	0.9300
C1—C2	1.396 (5)	C10—H10	0.9300
C1—C6	1.409 (4)	C11—H11	0.9300
C2—C3	1.369 (4)	C12—H12	0.9300
C3—C4	1.387 (5)	C13—H13	0.9300
C4—C5	1.357 (5)	C17—H17A	0.9700
C5—C6	1.406 (4)	C17—H17B	0.9700
C6—C7	1.422 (4)	C18—H18A	0.9700
C7—C8	1.494 (4)	C18—H18B	0.9700
C7—C14	1.381 (4)	C19—H19	0.9800
C8—C9	1.378 (4)	C20—H20A	0.9700
C8—C13	1.381 (4)	C20—H20B	0.9700
C9—C10	1.387 (4)	C21—H21A	0.9700
C10—C11	1.363 (5)	C21—H21B	0.9700
C11—C12	1.353 (5)	C22—H22A	0.9700
C12—C13	1.387 (5)	C22—H22B	0.9700
C14—C15	1.479 (4)	C23—H23A	0.9700
C16—C21	1.493 (5)	C23—H23B	0.9700
C16—C17	1.491 (5)	C24—H24A	0.9600
C17—C18	1.525 (5)	C24—H24B	0.9600
C18—C19	1.517 (5)	C24—H24C	0.9600

C1—N1—C14	109.5 (2)	C4—C5—H5	122.00
N3—N2—C15	119.7 (3)	C6—C5—H5	121.00
N2—N3—C16	117.2 (3)	C8—C9—H9	120.00
C1—N1—H1	125.00	C10—C9—H9	120.00
C14—N1—H1	125.00	C9—C10—H10	120.00
N3—N2—H2A	128.8 (18)	C11—C10—H10	120.00
C15—N2—H2A	111.5 (18)	C10—C11—H11	120.00
N1—C1—C6	107.2 (3)	C12—C11—H11	120.00
C2—C1—C6	121.9 (3)	C11—C12—H12	120.00
N1—C1—C2	130.9 (3)	C13—C12—H12	120.00
C1—C2—C3	117.7 (3)	C8—C13—H13	120.00
C2—C3—C4	120.1 (3)	C12—C13—H13	120.00
F1—C4—C3	117.0 (3)	C16—C17—H17A	110.00
C3—C4—C5	124.1 (3)	C16—C17—H17B	109.00
F1—C4—C5	118.9 (3)	C18—C17—H17A	110.00
C4—C5—C6	117.0 (3)	C18—C17—H17B	110.00
C1—C6—C5	119.3 (3)	H17A—C17—H17B	108.00
C5—C6—C7	133.2 (2)	C17—C18—H18A	109.00
C1—C6—C7	107.5 (2)	C17—C18—H18B	109.00
C6—C7—C14	106.3 (2)	C19—C18—H18A	109.00
C8—C7—C14	128.1 (2)	C19—C18—H18B	109.00
C6—C7—C8	125.5 (2)	H18A—C18—H18B	108.00
C7—C8—C13	120.0 (2)	C18—C19—H19	107.00
C9—C8—C13	117.9 (3)	C20—C19—H19	107.00
C7—C8—C9	122.1 (2)	C22—C19—H19	107.00
C8—C9—C10	120.8 (3)	C19—C20—H20A	109.00
C9—C10—C11	120.5 (3)	C19—C20—H20B	109.00
C10—C11—C12	119.4 (3)	C21—C20—H20A	109.00
C11—C12—C13	120.9 (3)	C21—C20—H20B	109.00
C8—C13—C12	120.6 (3)	H20A—C20—H20B	108.00
N1—C14—C15	117.7 (2)	C16—C21—H21A	110.00
C7—C14—C15	132.7 (2)	C16—C21—H21B	110.00
N1—C14—C7	109.5 (2)	C20—C21—H21A	110.00
N2—C15—C14	115.8 (2)	C20—C21—H21B	110.00
O1—C15—N2	122.8 (3)	H21A—C21—H21B	108.00
O1—C15—C14	121.4 (3)	C19—C22—H22A	108.00
N3—C16—C21	117.3 (3)	C19—C22—H22B	108.00
C17—C16—C21	113.7 (3)	C23—C22—H22A	108.00
N3—C16—C17	129.0 (3)	C23—C22—H22B	108.00
C16—C17—C18	110.7 (3)	H22A—C22—H22B	107.00
C17—C18—C19	113.2 (3)	C22—C23—H23A	109.00
C18—C19—C20	110.8 (3)	C22—C23—H23B	109.00
C18—C19—C22	112.6 (3)	C24—C23—H23A	109.00
C20—C19—C22	112.2 (3)	C24—C23—H23B	109.00
C19—C20—C21	112.8 (3)	H23A—C23—H23B	108.00
C16—C21—C20	110.0 (3)	C23—C24—H24A	109.00
C19—C22—C23	116.2 (4)	C23—C24—H24B	109.00
C22—C23—C24	114.1 (6)	C23—C24—H24C	109.00
C1—C2—H2	121.00	H24A—C24—H24B	110.00
C3—C2—H2	121.00	H24A—C24—H24C	109.00
C2—C3—H3	120.00	H24B—C24—H24C	110.00
C4—C3—H3	120.00

C1—N1—C14—C15	−178.2 (2)	C14—C7—C8—C13	79.6 (4)
C14—N1—C1—C2	176.9 (3)	C14—C7—C8—C9	−101.6 (3)
C14—N1—C1—C6	−0.2 (3)	C8—C7—C14—C15	2.2 (5)
C1—N1—C14—C7	0.0 (3)	C6—C7—C8—C13	−95.4 (3)
C15—N2—N3—C16	174.8 (3)	C9—C8—C13—C12	1.3 (5)
N3—N2—C15—O1	7.1 (5)	C7—C8—C13—C12	−179.9 (3)
N3—N2—C15—C14	−174.2 (2)	C7—C8—C9—C10	179.6 (3)
N2—N3—C16—C21	−177.8 (3)	C13—C8—C9—C10	−1.6 (4)
N2—N3—C16—C17	−1.1 (5)	C8—C9—C10—C11	1.0 (5)
C2—C1—C6—C7	−177.2 (3)	C9—C10—C11—C12	0.2 (5)
N1—C1—C2—C3	−177.8 (3)	C10—C11—C12—C13	−0.5 (5)
C6—C1—C2—C3	−1.0 (4)	C11—C12—C13—C8	−0.2 (5)
N1—C1—C6—C7	0.3 (3)	N1—C14—C15—N2	−167.4 (3)
C2—C1—C6—C5	1.1 (4)	C7—C14—C15—O1	−166.4 (3)
N1—C1—C6—C5	178.6 (2)	C7—C14—C15—N2	14.9 (5)
C1—C2—C3—C4	0.6 (4)	N1—C14—C15—O1	11.3 (4)
C2—C3—C4—F1	−179.6 (3)	N3—C16—C17—C18	−122.2 (4)
C2—C3—C4—C5	−0.3 (5)	C21—C16—C17—C18	54.6 (4)
C3—C4—C5—C6	0.4 (4)	N3—C16—C21—C20	121.6 (3)
F1—C4—C5—C6	179.7 (2)	C17—C16—C21—C20	−55.6 (4)
C4—C5—C6—C7	177.0 (3)	C16—C17—C18—C19	−52.3 (4)
C4—C5—C6—C1	−0.8 (4)	C17—C18—C19—C20	51.8 (4)
C5—C6—C7—C8	−2.3 (5)	C17—C18—C19—C22	178.4 (3)
C1—C6—C7—C14	−0.2 (3)	C18—C19—C20—C21	−52.9 (4)
C5—C6—C7—C14	−178.2 (3)	C22—C19—C20—C21	−179.7 (3)
C1—C6—C7—C8	175.7 (2)	C18—C19—C22—C23	63.2 (5)
C6—C7—C14—N1	0.1 (3)	C20—C19—C22—C23	−170.9 (4)
C6—C7—C8—C9	83.4 (4)	C19—C20—C21—C16	54.5 (4)
C6—C7—C14—C15	178.0 (3)	C19—C22—C23—C24	176.7 (5)
C8—C7—C14—N1	−175.6 (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···A	D—H	H···A	D···A	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···Cg1^iv	0.93	2.89	3.683 (3)	144
C17—H17A···Cg2^v	0.97	2.81	3.571 (3)	136
C17—H17B···Cg3	0.97	2.90	3.810 (4)	157

Symmetry codes: (i) −x+3/2, −y+1/2, z+1/2; (ii) y+1, −x+1, −z+1; (iii) −y+1, x−1, −z+1; (iv) y+1, −x+1, −z; (v) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆FN₃O
M_r	391.48
Crystal system, space group	Tetragonal, I4
Temperature (K)	296
a, c (Å)	22.6986 (11), 8.4480 (5)
V (Å³)	4352.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.63 × 0.46 × 0.28

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (Stoe & Cie, 2002)
T_min, T_max	0.957, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	15640, 4531, 3430
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.092, 1.03
No. of reflections	4531
No. of parameters	267
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···Cg1^iv	0.93	2.89	3.683 (3)	144
C17—H17A···Cg2^v	0.97	2.81	3.571 (3)	136
C17—H17B···Cg3	0.97	2.90	3.810 (4)	157

Symmetry codes: (i) −x+3/2, −y+1/2, z+1/2; (ii) y+1, −x+1, −z+1; (iii) −y+1, x−1, −z+1; (iv) y+1, −x+1, −z; (v) x, y, z−1.

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

Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Zopun, M., Çapan, G. & Büyükgüngör, O. (2013). Acta Cryst. E69, o1137. CSD CrossRef IUCr Journals Google Scholar
Cihan-Üstündağ, G. & Çapan, G. (2012). Mol. Divers. 16, 525–539. Web of Science PubMed Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar

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