5-Fluoro-N′-[(E)-4-methoxy­benzyl­idene]-3-phenyl-1H-indole-2-carbohydrazide

Akkurt, M.; Çelik, Í.; Cihan, G.; Çapan, G.; Büyükgüngör, O.

doi:10.1107/S1600536810009098

5-Fluoro-N′-[(E)-4-methoxybenzylidene]-3-phenyl-1H-indole-2-carbohydrazide

M. Akkurt, Í. Çelik, G. Cihan, G. Çapan and O. Büyükgüngör

In the title molecule, C₂₃H₁₈FN₃O₂, the mean plane of the indole system forms dihedral angles of 44.23 (8) and 14.54 (7)°, respectively, with the phenyl and benzene rings. In the crystal, intermolecular N—H

O hydrogen bonds link molecules into two-layer ribbons extended along the b axis. The crystal packing also exhibits weak intermolecular C—H

O, C—H

F and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810009098/cv2701sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810009098/cv2701Isup2.hkl Contains datablock I

CCDC reference: 774272

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.038
wR factor = 0.096
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     --  C15     ..       5.29 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    --  C18     ..       5.41 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the framework of our ongoing project directed towards the design, synthesis and characterization of bioactive indole derivatives (Akkurt et al., 2009; Güzel et al., 2006; Kaynak et al., 2005), we report here the synthesis and crystal structure of the title compound.

In the title molecule (Fig. 1), bond lengths and bond angles are all within expected values (Allen et al., 1987). The nine-membered indole ring [a maximum deviation from the mean plane of 0.039 (2) Å for C6] makes dihedral angles of 44.23 (8)° and 14.54 (7)°, respectively, with the phenyl ring (C9–C14) and benzene ring (C17–C22). The (C9–C14) and (C17–C22) rings form a dihedral angle of 36.87 (9)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link molecules into two-layer ribbons extended along b axis. The crystal packing exhibits also weak intermolecular C—H···O, C—H···F and C—H···π interactions (Table 1).

Related literature top

For the synthesis and characterization of related indole derivatives, see: Akkurt et al. (2009); Güzel et al. (2006); Kaynak et al. (2005). For typical values of bond lengths in organic compounds, see: Allen et al. (1987).

Experimental top

A mixture of 5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (0.005 mol), 4-methoxy benzaldehyde (0.006 mol) and 15 ml of absolute ethanol was heated on a water bath for 4 h. The crude product obtained on cooling was filtered and purified by recrystallization from ethanol/chloroform (1/1). [Yield: 93.8 %, m.p.: 493-493 K]. IR (KBr) ν = 3247 (N—H), 1635 (C=O), 1622 (C=N) cm^-1; ¹H-NMR (DMSO-d₆, 500 MHz) δ = 3.78 (3H, s, 4-OCH₃), 6.99 (2H, d*, J=6.8 Hz, H3,H5-benzylidene), 7.14 (1H, t*, J=8.8 Hz, H6-indole), 7.31-7.52 (7H, m, H4, H7, 3-C₆H₅-indole), 7.62 (2H, d*, J=5.9 Hz, H2, H6-benzylidene), 8.02 (1H, s, N=CH), 11.23 (1H, s, CONH), 12.02 (1H, s, NH-indole) ppm ( * = broad). Analysis calculated for C₂₃H₁₈FN₃O₂ : C 71.31, H 4.68, N 10.85 %. Found : C 71.22, H 3.94, N 10.82 %.

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 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of the title molecule showing the atomic numbering and 50% probability displacement ellipsoids.

5-Fluoro-N'-[(E)-4-methoxybenzylidene]-3-phenyl- 1H-indole-2-carbohydrazide top

Crystal data top

C₂₃H₁₈FN₃O₂	F(000) = 808
M_r = 387.40	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8633 reflections
a = 19.5709 (11) Å	θ = 1.8–27.3°
b = 5.1546 (2) Å	µ = 0.09 mm⁻¹
c = 24.3584 (14) Å	T = 296 K
β = 127.686 (3)°	Plate, colourless
V = 1944.63 (19) Å³	0.60 × 0.38 × 0.07 mm
Z = 4

Data collection top

Stoe IPDS2 diffractometer	4053 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2900 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.038
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.3°
ω scans	h = −24→24
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→6
T_min = 0.958, T_max = 0.994	l = −30→30
23274 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0532P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4053 reflections	Δρ_max = 0.12 e Å⁻³
264 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0123 (12)

Crystal data top

C₂₃H₁₈FN₃O₂	V = 1944.63 (19) Å³
M_r = 387.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.5709 (11) Å	µ = 0.09 mm⁻¹
b = 5.1546 (2) Å	T = 296 K
c = 24.3584 (14) Å	0.60 × 0.38 × 0.07 mm
β = 127.686 (3)°

Data collection top

Stoe IPDS2 diffractometer	4053 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2900 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.994	R_int = 0.038
23274 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.03	Δρ_max = 0.12 e Å⁻³
4053 reflections	Δρ_min = −0.13 e Å⁻³
264 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 esds 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	0.96473 (6)	0.3955 (3)	0.67120 (6)	0.1153 (5)
O1	0.46022 (6)	0.08712 (18)	0.41796 (5)	0.0624 (3)
O2	−0.00747 (7)	0.7292 (3)	0.05087 (6)	0.0898 (4)
N1	0.62743 (7)	0.1715 (2)	0.53758 (5)	0.0565 (4)
N2	0.45250 (7)	0.5105 (2)	0.38898 (6)	0.0532 (4)
N3	0.36665 (7)	0.4917 (2)	0.33221 (6)	0.0553 (4)
C1	0.71455 (9)	0.2113 (3)	0.57970 (7)	0.0560 (4)
C2	0.77885 (11)	0.0917 (3)	0.64212 (8)	0.0747 (6)
C3	0.86269 (11)	0.1589 (4)	0.67208 (8)	0.0867 (7)
C4	0.87981 (9)	0.3381 (4)	0.63954 (8)	0.0778 (6)
C5	0.81907 (9)	0.4567 (3)	0.57871 (7)	0.0637 (5)
C6	0.73246 (8)	0.3953 (3)	0.54742 (6)	0.0505 (4)
C7	0.65172 (8)	0.4668 (2)	0.48304 (6)	0.0464 (4)
C8	0.58921 (8)	0.3256 (2)	0.47996 (6)	0.0480 (4)
C9	0.64238 (8)	0.6238 (2)	0.42835 (6)	0.0465 (4)
C10	0.69245 (9)	0.8454 (2)	0.44513 (8)	0.0567 (4)
C11	0.68968 (10)	0.9792 (3)	0.39482 (10)	0.0702 (6)
C12	0.63650 (11)	0.8975 (3)	0.32699 (10)	0.0775 (7)
C13	0.58566 (10)	0.6816 (3)	0.30908 (8)	0.0686 (5)
C14	0.58882 (8)	0.5452 (3)	0.35932 (7)	0.0544 (4)
C15	0.49563 (8)	0.2983 (3)	0.42673 (6)	0.0493 (4)
C16	0.33397 (9)	0.6934 (3)	0.29425 (7)	0.0565 (5)
C17	0.24446 (8)	0.6999 (3)	0.23225 (7)	0.0546 (4)
C18	0.21612 (10)	0.8892 (3)	0.18233 (9)	0.0710 (6)
C19	0.13225 (11)	0.8934 (3)	0.12238 (9)	0.0781 (6)
C20	0.07431 (9)	0.7099 (3)	0.11180 (8)	0.0672 (5)
C21	0.10054 (10)	0.5219 (3)	0.16103 (8)	0.0712 (5)
C22	0.18461 (9)	0.5177 (3)	0.22030 (8)	0.0665 (5)
C23	−0.06706 (11)	0.5297 (4)	0.03519 (11)	0.0994 (8)
H1	0.60070	0.06620	0.54590	0.0680*
H2	0.76550	−0.02890	0.66270	0.0900*
H2A	0.47840	0.65790	0.40020	0.0640*
H3	0.90770	0.08460	0.71400	0.1040*
H5	0.83390	0.57360	0.55850	0.0760*
H10	0.72810	0.90370	0.49080	0.0680*
H11	0.72400	1.12550	0.40680	0.0840*
H12	0.63490	0.98820	0.29320	0.0930*
H13	0.54910	0.62740	0.26310	0.0820*
H14	0.55460	0.39840	0.34680	0.0650*
H16	0.36820	0.84010	0.30650	0.0680*
H18	0.25450	1.01630	0.18940	0.0850*
H19	0.11480	1.02040	0.08910	0.0940*
H21	0.06150	0.39790	0.15420	0.0850*
H22	0.20180	0.38940	0.25320	0.0800*
H23A	−0.04400	0.36500	0.03540	0.1490*
H23B	−0.12070	0.56020	−0.00980	0.1490*
H23C	−0.07670	0.52920	0.06940	0.1490*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0444 (5)	0.1659 (11)	0.0877 (7)	0.0028 (6)	0.0158 (5)	−0.0115 (7)
O1	0.0607 (6)	0.0602 (6)	0.0590 (6)	−0.0204 (5)	0.0328 (5)	−0.0045 (4)
O2	0.0559 (7)	0.1070 (9)	0.0738 (7)	0.0105 (6)	0.0229 (6)	0.0101 (7)
N1	0.0587 (7)	0.0636 (7)	0.0512 (6)	−0.0052 (5)	0.0357 (6)	0.0048 (5)
N2	0.0418 (6)	0.0510 (6)	0.0596 (7)	−0.0069 (5)	0.0273 (5)	−0.0058 (5)
N3	0.0421 (6)	0.0623 (7)	0.0557 (6)	−0.0046 (5)	0.0270 (5)	−0.0076 (5)
C1	0.0562 (8)	0.0663 (8)	0.0436 (7)	0.0036 (7)	0.0296 (7)	−0.0009 (6)
C2	0.0781 (11)	0.0916 (11)	0.0505 (8)	0.0176 (9)	0.0373 (8)	0.0118 (8)
C3	0.0666 (11)	0.1203 (15)	0.0461 (8)	0.0268 (10)	0.0205 (8)	0.0064 (9)
C4	0.0457 (8)	0.1054 (13)	0.0574 (9)	0.0035 (8)	0.0187 (8)	−0.0120 (9)
C5	0.0477 (8)	0.0754 (9)	0.0565 (8)	−0.0037 (7)	0.0260 (7)	−0.0089 (7)
C6	0.0462 (7)	0.0571 (7)	0.0434 (7)	−0.0029 (6)	0.0249 (6)	−0.0067 (6)
C7	0.0442 (7)	0.0484 (7)	0.0450 (7)	−0.0053 (5)	0.0264 (6)	−0.0050 (5)
C8	0.0488 (7)	0.0504 (7)	0.0446 (7)	−0.0046 (6)	0.0285 (6)	−0.0021 (6)
C9	0.0426 (6)	0.0467 (6)	0.0531 (7)	0.0014 (5)	0.0307 (6)	0.0012 (5)
C10	0.0521 (7)	0.0503 (7)	0.0696 (9)	−0.0029 (6)	0.0382 (7)	−0.0014 (6)
C11	0.0626 (9)	0.0576 (8)	0.0977 (13)	0.0018 (7)	0.0528 (10)	0.0177 (8)
C12	0.0767 (11)	0.0853 (11)	0.0863 (12)	0.0158 (9)	0.0580 (10)	0.0338 (10)
C13	0.0667 (9)	0.0824 (10)	0.0571 (8)	0.0094 (8)	0.0380 (8)	0.0131 (8)
C14	0.0503 (7)	0.0584 (8)	0.0519 (8)	0.0003 (6)	0.0299 (7)	0.0038 (6)
C15	0.0494 (7)	0.0548 (7)	0.0472 (7)	−0.0108 (6)	0.0314 (6)	−0.0074 (6)
C16	0.0528 (8)	0.0566 (8)	0.0606 (8)	−0.0048 (6)	0.0349 (7)	−0.0101 (7)
C17	0.0506 (7)	0.0562 (7)	0.0556 (8)	0.0026 (6)	0.0318 (7)	−0.0065 (6)
C18	0.0625 (9)	0.0616 (9)	0.0798 (11)	−0.0024 (7)	0.0388 (9)	0.0014 (8)
C19	0.0693 (10)	0.0719 (10)	0.0750 (10)	0.0081 (8)	0.0349 (9)	0.0150 (8)
C20	0.0513 (8)	0.0749 (10)	0.0608 (9)	0.0086 (7)	0.0268 (7)	−0.0027 (8)
C21	0.0516 (8)	0.0766 (10)	0.0718 (10)	−0.0047 (7)	0.0308 (8)	0.0023 (8)
C22	0.0538 (8)	0.0694 (9)	0.0637 (9)	−0.0012 (7)	0.0295 (7)	0.0068 (7)
C23	0.0472 (9)	0.1322 (17)	0.0881 (13)	−0.0010 (10)	0.0257 (9)	−0.0051 (12)

Geometric parameters (Å, º) top

F1—C4	1.370 (2)	C12—C13	1.374 (3)
O1—C15	1.2369 (19)	C13—C14	1.380 (2)
O2—C20	1.367 (2)	C16—C17	1.455 (2)
O2—C23	1.421 (3)	C17—C22	1.386 (3)
N1—C1	1.365 (2)	C17—C18	1.383 (2)
N1—C8	1.3699 (15)	C18—C19	1.377 (3)
N2—N3	1.3798 (19)	C19—C20	1.375 (3)
N2—C15	1.3437 (18)	C20—C21	1.374 (2)
N3—C16	1.2735 (18)	C21—C22	1.374 (3)
N1—H1	0.8600	C2—H2	0.9300
N2—H2A	0.8600	C3—H3	0.9300
C1—C2	1.391 (2)	C5—H5	0.9300
C1—C6	1.406 (2)	C10—H10	0.9300
C2—C3	1.371 (3)	C11—H11	0.9300
C3—C4	1.385 (3)	C12—H12	0.9300
C4—C5	1.352 (2)	C13—H13	0.9300
C5—C6	1.405 (3)	C14—H14	0.9300
C6—C7	1.4360 (19)	C16—H16	0.9300
C7—C8	1.386 (2)	C18—H18	0.9300
C7—C9	1.4715 (18)	C19—H19	0.9300
C8—C15	1.467 (2)	C21—H21	0.9300
C9—C14	1.3911 (18)	C22—H22	0.9300
C9—C10	1.3937 (19)	C23—H23A	0.9600
C10—C11	1.378 (3)	C23—H23B	0.9600
C11—C12	1.374 (3)	C23—H23C	0.9600

F1···H3ⁱ	2.5400	C14···H11ⁱⁱⁱ	3.0500
F1···H21ⁱⁱ	2.6500	C15···H1^iv	3.0100
O1···N1	2.7803 (16)	C15···H14	2.8500
O1···N2ⁱⁱⁱ	3.0373 (14)	C16···H12^ix	2.7600
O1···N3	2.7182 (15)	C17···H12^ix	2.9900
O1···C16ⁱⁱⁱ	3.1939 (18)	C21···H23C	2.7500
O1···N1^iv	2.8573 (19)	C21···H23A	2.7300
O1···H2Aⁱⁱⁱ	2.3200	C23···H21	2.5100
O1···H16ⁱⁱⁱ	2.5000	C23···H5^x	3.1000
O1···H1	2.6100	H1···O1	2.6100
O1···H1^iv	2.0300	H1···O1^iv	2.0300
O2···H23A^v	2.8700	H1···C15^iv	3.0100
N1···O1	2.7803 (16)	H2···H22^iv	2.5400
N1···O1^iv	2.8573 (19)	H2A···O1^vi	2.3200
N2···O1^vi	3.0373 (14)	H2A···C7	2.8600
N2···C9	3.273 (2)	H2A···C9	2.8500
N2···C14	3.167 (2)	H2A···C14	2.9400
N3···O1	2.7182 (15)	H2A···H16	2.1700
N2···H14	2.8100	H3···F1^xi	2.5400
N3···H22	2.6100	H5···C10	2.8100
C1···C10ⁱⁱⁱ	3.572 (2)	H5···H10	2.3900
C2···C22^vii	3.587 (2)	H5···C23^viii	3.1000
C2···C16^vii	3.562 (3)	H5···H23C^viii	2.6000
C2···C17^vii	3.526 (3)	H10···C1^vi	2.8200
C5···C10	3.299 (2)	H10···C5	2.9000
C6···C10ⁱⁱⁱ	3.5313 (19)	H10···C6	2.9400
C7···C10ⁱⁱⁱ	3.5564 (17)	H10···C6^vi	2.8600
C9···N2	3.273 (2)	H10···H5	2.3900
C10···C7^vi	3.5564 (17)	H11···C14^vi	3.0500
C10···C6^vi	3.5313 (19)	H11···H23B^viii	2.5900
C10···C5	3.299 (2)	H12···C16^xii	2.7600
C10···C1^vi	3.572 (2)	H12···C17^xii	2.9900
C11···C14^vi	3.327 (2)	H13···H14^xii	2.5700
C14···N2	3.167 (2)	H14···N2	2.8100
C14···C15	3.362 (2)	H14···C8	2.9000
C14···C11ⁱⁱⁱ	3.327 (2)	H14···C11ⁱⁱⁱ	3.0400
C15···C14	3.362 (2)	H14···C15	2.8500
C16···C2^vii	3.562 (3)	H14···H13^ix	2.5700
C16···O1^vi	3.1939 (18)	H16···O1^vi	2.5000
C17···C2^vii	3.526 (3)	H16···H2A	2.1700
C18···C22^vi	3.525 (2)	H16···H18	2.4800
C19···C21^vi	3.533 (2)	H18···H16	2.4800
C21···C19ⁱⁱⁱ	3.533 (2)	H21···C23	2.5100
C22···C18ⁱⁱⁱ	3.525 (2)	H21···H23A	2.3200
C22···C2^vii	3.587 (2)	H21···H23C	2.2800
C1···H10ⁱⁱⁱ	2.8200	H21···F1^xiii	2.6500
C4···H23Cⁱⁱ	3.0000	H22···N3	2.6100
C5···H10	2.9000	H22···H2^iv	2.5400
C6···H10ⁱⁱⁱ	2.8600	H23A···C21	2.7300
C6···H10	2.9400	H23A···H21	2.3200
C7···H2A	2.8600	H23A···O2^v	2.8700
C8···H14	2.9000	H23B···C11^x	2.9400
C9···H2A	2.8500	H23B···H11^x	2.5900
C10···H5	2.8100	H23C···C21	2.7500
C11···H23B^viii	2.9400	H23C···H21	2.2800
C11···H14^vi	3.0400	H23C···C4^xiii	3.0000
C14···H2A	2.9400	H23C···H5^x	2.6000

C20—O2—C23	117.57 (15)	C16—C17—C18	120.67 (16)
C1—N1—C8	109.37 (13)	C17—C18—C19	121.38 (18)
N3—N2—C15	119.95 (11)	C18—C19—C20	119.99 (16)
N2—N3—C16	115.70 (13)	O2—C20—C19	115.94 (15)
C8—N1—H1	125.00	C19—C20—C21	119.76 (17)
C1—N1—H1	125.00	O2—C20—C21	124.30 (17)
N3—N2—H2A	120.00	C20—C21—C22	119.78 (18)
C15—N2—H2A	120.00	C17—C22—C21	121.69 (15)
N1—C1—C2	129.38 (17)	C1—C2—H2	121.00
N1—C1—C6	107.75 (12)	C3—C2—H2	121.00
C2—C1—C6	122.80 (18)	C2—C3—H3	120.00
C1—C2—C3	117.27 (18)	C4—C3—H3	120.00
C2—C3—C4	119.55 (16)	C4—C5—H5	122.00
F1—C4—C5	118.06 (18)	C6—C5—H5	121.00
C3—C4—C5	124.78 (19)	C9—C10—H10	120.00
F1—C4—C3	117.16 (16)	C11—C10—H10	120.00
C4—C5—C6	116.96 (16)	C10—C11—H11	120.00
C5—C6—C7	133.76 (14)	C12—C11—H11	120.00
C1—C6—C5	118.62 (13)	C11—C12—H12	120.00
C1—C6—C7	107.44 (14)	C13—C12—H12	120.00
C8—C7—C9	128.53 (12)	C12—C13—H13	120.00
C6—C7—C9	125.07 (15)	C14—C13—H13	120.00
C6—C7—C8	105.66 (11)	C9—C14—H14	120.00
N1—C8—C15	117.04 (13)	C13—C14—H14	119.00
C7—C8—C15	133.02 (11)	N3—C16—H16	119.00
N1—C8—C7	109.76 (13)	C17—C16—H16	119.00
C7—C9—C10	120.62 (11)	C17—C18—H18	119.00
C7—C9—C14	121.26 (12)	C19—C18—H18	119.00
C10—C9—C14	117.93 (13)	C18—C19—H19	120.00
C9—C10—C11	120.73 (14)	C20—C19—H19	120.00
C10—C11—C12	120.33 (17)	C20—C21—H21	120.00
C11—C12—C13	119.95 (18)	C22—C21—H21	120.00
C12—C13—C14	120.00 (15)	C17—C22—H22	119.00
C9—C14—C13	121.05 (15)	C21—C22—H22	119.00
N2—C15—C8	116.70 (13)	O2—C23—H23A	109.00
O1—C15—N2	123.16 (14)	O2—C23—H23B	109.00
O1—C15—C8	120.14 (13)	O2—C23—H23C	109.00
N3—C16—C17	121.61 (15)	H23A—C23—H23B	109.00
C16—C17—C22	121.94 (14)	H23A—C23—H23C	110.00
C18—C17—C22	117.39 (15)	H23B—C23—H23C	109.00

C23—O2—C20—C19	174.44 (18)	C6—C7—C8—N1	−1.05 (15)
C23—O2—C20—C21	−5.2 (3)	C9—C7—C8—C15	−5.4 (2)
C1—N1—C8—C15	176.77 (13)	C6—C7—C9—C10	−43.7 (2)
C1—N1—C8—C7	1.04 (16)	C8—C7—C9—C14	−37.6 (2)
C8—N1—C1—C2	−177.67 (17)	C9—C7—C8—N1	169.40 (13)
C8—N1—C1—C6	−0.58 (17)	N1—C8—C15—N2	150.12 (13)
N3—N2—C15—O1	−7.9 (2)	N1—C8—C15—O1	−30.4 (2)
C15—N2—N3—C16	−171.16 (16)	C7—C8—C15—N2	−35.4 (2)
N3—N2—C15—C8	171.54 (14)	C7—C8—C15—O1	144.08 (15)
N2—N3—C16—C17	179.22 (15)	C10—C9—C14—C13	0.3 (3)
N1—C1—C2—C3	176.36 (17)	C7—C9—C10—C11	173.95 (17)
N1—C1—C6—C7	−0.07 (18)	C14—C9—C10—C11	−1.0 (3)
N1—C1—C6—C5	−175.83 (14)	C7—C9—C14—C13	−174.61 (17)
C2—C1—C6—C7	177.25 (15)	C9—C10—C11—C12	0.8 (3)
C6—C1—C2—C3	−0.3 (3)	C10—C11—C12—C13	0.1 (3)
C2—C1—C6—C5	1.5 (2)	C11—C12—C13—C14	−0.8 (3)
C1—C2—C3—C4	−0.4 (3)	C12—C13—C14—C9	0.6 (3)
C2—C3—C4—F1	−179.10 (17)	N3—C16—C17—C22	16.5 (3)
C2—C3—C4—C5	0.0 (3)	N3—C16—C17—C18	−162.92 (18)
C3—C4—C5—C6	1.2 (3)	C16—C17—C22—C21	−178.75 (17)
F1—C4—C5—C6	−179.77 (15)	C18—C17—C22—C21	0.7 (3)
C4—C5—C6—C1	−1.8 (2)	C16—C17—C18—C19	178.02 (18)
C4—C5—C6—C7	−176.23 (17)	C22—C17—C18—C19	−1.4 (3)
C5—C6—C7—C8	175.53 (17)	C17—C18—C19—C20	1.3 (3)
C5—C6—C7—C9	4.7 (3)	C18—C19—C20—C21	−0.4 (3)
C1—C6—C7—C9	−170.19 (12)	C18—C19—C20—O2	179.97 (18)
C1—C6—C7—C8	0.68 (16)	O2—C20—C21—C22	179.27 (18)
C6—C7—C9—C14	131.12 (17)	C19—C20—C21—C22	−0.4 (3)
C6—C7—C8—C15	−175.85 (15)	C20—C21—C22—C17	0.2 (3)
C8—C7—C9—C10	147.59 (16)

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+1, −y+1/2, z+1/2; (iii) x, y−1, z; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z; (vi) x, y+1, z; (vii) −x+1, −y+1, −z+1; (viii) x+1, −y+3/2, z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) x−1, −y+3/2, z−1/2; (xi) −x+2, y−1/2, −z+3/2; (xii) −x+1, y+1/2, −z+1/2; (xiii) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/C6–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^iv	0.86	2.03	2.8573 (19)	162
N2—H2A···O1^vi	0.86	2.32	3.0373 (14)	141
C3—H3···F1^xi	0.93	2.54	3.473 (2)	177
C16—H16···O1^vi	0.93	2.50	3.1939 (18)	131
C10—H10···Cg1^vi	0.93	2.85	3.3736 (17)	117

Symmetry codes: (iv) −x+1, −y, −z+1; (vi) x, y+1, z; (xi) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈FN₃O₂
M_r	387.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	19.5709 (11), 5.1546 (2), 24.3584 (14)
β (°)	127.686 (3)
V (Å³)	1944.63 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.38 × 0.07

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.958, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	23274, 4053, 2900
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.03
No. of reflections	4053
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).