5-Fluoro-3-phenyl-N'-(4-propyl-cyclo-hexyl-idene)-1H-indole-2-carbohydrazide.

In the title compound, C24H26FN3O, the cyclo-hexane 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 intra-molecular C-H⋯π contact occurs. In the crystal, pairs of mol-ecules related by a crystallographic twofold axis are linked by bifurcated N-H⋯(O,N) hydrogen bonds; a C-H⋯O inter-action occurs between the same pair. The dimers are linked by C-H⋯F and C-H⋯π inter-actions, 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 ▶); n class="Chemical">Cihan-Üstündağ & Çapan (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H26FN3O

M = 391.48

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 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

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018333/hb7101sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018333/hb7101Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H26FN3O	Dx = 1.195 Mg m−3
Mr = 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

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	Rint = 0.066
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.5°
ω–scans	h = −28→27
Absorption correction: integration (Stoe & Cie, 2002)	k = −28→28
Tmin = 0.957, Tmax = 0.978	l = −10→10
15640 measured reflections

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	Δρmax = 0.13 e Å−3
267 parameters	Δρmin = −0.11 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg1iv	0.93	2.89	3.683 (3)	144
C17—H17A···Cg2v	0.97	2.81	3.571 (3)	136
C17—H17B···Cg3	0.97	2.90	3.810 (4)	157

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⋯Cg1iv	0.93	2.89	3.683 (3)	144
C17—H17A⋯Cg2v	0.97	2.81	3.571 (3)	136
C17—H17B⋯Cg3	0.97	2.90	3.810 (4)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .