1-(4-Fluoro­benz­yl)-2-(pyridin-2-yl)-1H-benzimidazole

Çelik, Ö.; Anĝay, F.; Gündoĝan, M.; Ulusoy, M.

doi:10.1107/S1600536814005947

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o485

doi:10.1107/S1600536814005947

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1-(4-Fluorobenzyl)-2-(pyridin-2-yl)-1H-benzimidazole

Ömer Çelik,^a ^* Fırat Anĝay,^b Mustafa Gündoĝan ^c and Mahmut Ulusoy ^c

^aDepartment of Physics, Faculty of Education, Dicle University, 21280, Diyarbakır, Turkey, ^bDepartment of Physics, Institute of Sciences, Dicle University, 21280, Diyarbakır, Turkey, and ^cDepartment of Chemistry, Faculty of Science & Art, Harran University, 63300, Şanlıurfa, Turkey
^*Correspondence e-mail: omer.celik@dicle.edu.tr

(Received 27 February 2014; accepted 17 March 2014; online 26 March 2014)

In the title compound, C₁₉H₁₄FN₃, the dihedral angles between the benzimidazole unit (r.m.s. deviation= 0.017 Å) and the pyridine and benzene rings are 24.46 (4) and 81.87 (3)°, respectively. In the crystal, molecules are stacked along the a-axis direction by C—H⋯π interactions.

CCDC reference: 992223

Related literature

For the use of 2-(2-pyridyl)benzimidazole in coordination chemistry, see: Boca et al. (1997 ); De Castro et al. (1991 ); Khalil et al. (2001 ); Maekawa et al. (1994 ). For deprotonation of the NH group in 2-(2-pyridyl)benzimidazole, see: Chiswell et al. (1964 ); Harkins et al. (1956 ); Haga (1983 ). For functionalization of 2-(2-pyridyl)benzimidazole, see: Ali et al. (1998 ); Hossain et al. (2001 ); Sahin et al. (2010 ). For related structures, see: Çelik et al. (2007 , 2009 ).

Experimental

Crystal data

C₁₉H₁₄FN₃
M_r = 303.33
Monoclinic, P 2₁ /c
a = 4.7363 (5) Å
b = 15.4102 (17) Å
c = 20.953 (2) Å
β = 95.363 (8)°
V = 1522.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.984, T_max = 0.984
13325 measured reflections
3133 independent reflections
2355 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 0.93
3133 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgⁱ	0.97	2.94	3.486 (2)	117
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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

CCDC reference: 992223

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814005947/bq2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005947/bq2393Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005947/bq2393Isup3.cml

checkCIF report

Comment top

The N—N type ligand system, 2-(2-pyridyl)benzimidazole has a venerable history in coordination chemistry (Harkins et al., 1956; Chiswell et al., 1964; De Castro et al., 1991; Maekawa et al., 1994; Khalil et al., 2001; Boca et al., 1997). Many of the reported complexes of 2-(2-pyridyl) benzimidazole have been of interest because of the possibility of deprotonation of the NH group of the imidazole unit, converting the ligand from neutral to anionic form with different properties (Harkins et al., 1956; Chiswell et al., 1964; Haga, 1983). The functionalization of 2-(2-pyridyl)benzimidazole at the externally directed NH position allows simple incorporation of 2-(2-pyridyl)benzimidazole units (Sahin et al., 2010; Hossain et al., 2001; Ali et al., 1998).

The molecular structure of title compound is shown in Figure 1. In the compound, the bond lengths of F—C17, N3—C12 and C1—C2 are 1.3671 (18) Å, 1.336 (2) Å and 1.373 (2) Å, respectively. C18—C17—F and N3—C8—C7 bond angles are 118.58 (13)° and 117.91 (13)°. F—C17—C18—C19 and C12—N3—C8—C7 torsion angles are -178.74 (15)° and -178.95 (14)°. Similar results are observed in the study of (Çelik et al., 2009; Çelik et al., 2007).

In the title compound, (Fig. 1), four planes were named as P1(N1/C5/C6/N2/C7), P2(N3/C8/C9/C10/C11/C12), P3(C1/C2/C3/C4/C5/C6), P4(C14/C15/C16/C17/C18/C19) and P5(N1/C5/C4/C3/C2/C1/C6/N2/C7). The five- and six-membered rings (N1/C5/C6/N2/C7) and (C1—C6) of the benzimidazole groups are almost co-planar with maximum deviations of -0.011Å for C5 and -0.017 Å for C6, respectively. Moreover the maximum deviations from P2 plane of C8, P4 plane of C17 and P5 plane of N2 are -0.007 Å, -0.003 Å and -0.034 Å, respectively.

In the compound, dihedral angles between P1—P2, P1—P3, P1—P4, P1—P5, P2—P3, P2—P4, P2—P5, P3—P4, P3—P5 and P4—P5 are 23.37 (5)°, 2.29 (5)°, 81.87 (3)°, 1.18 (4)°, 25.51 (5)°, and 73.68 (4)°, 24.46 (4)°, 81.94 (4)°, 1.11 (4)° and 81.87 (3)° respectively.

There is intermolecular C—H···Cg(π) type hydrogen bonds interactions in the crystal structure with the contact distances of 2.9345 Å between acceptor and donor atom and π-ring system defined as C1–C6 ring (Table 1.) and the molecules are stacked along a-axis with these C—H···π type hydrogen-bond interactions (Figure 2.).

Related literature top

For the use of 2-(2-pyridyl)benzimidazole in coordination chemistry, see: Boca et al. (1997); De Castro et al. (1991); Khalil et al. (2001); Maekawa et al. (1994). For deprotonation of the NH group in 2-(2-pyridyl)benzimidazole, see: Chiswell et al. (1964); Harkins et al. (1956); Haga (1983). For functionalization of 2-(2-pyridyl)benzimidazole, see: Ali et al. (1998); Hossain et al. (2001); Sahin et al. (2010). For related structures, see: Çelik et al. (2007, 2009).

Experimental top

A solution of the 2-pyridiylbenzimidazole (1.95 g, 10.0 mmol) in toluene (10 ml) and KOH was added (616 mg, 11.0 mmol) and stirred at 60 °C for 4 h. To this reaction mixture 4-florobenzyl bromide (1.89 g, 10.0 mmol) was added, then heated at this temperature for 24 h. Then volatiles were evaporated in vacuum to dryness. The residue was dissolved in CH₂Cl₂ and filtered via cannula on celite. The desired product was obtained after concentration of CH₂Cl₂ (15 ml) and then precipitating with hexane (30 ml). The off-white solid obtained in 80% yield. M.p. 94 °C. ¹H NMR (400 MHz, CDCl₃, δ p.p.m.): 6.13 (s, 2H, N—CH₂); 6.90–6.94 (t, J = 8.0 Hz, 2H, Ar—CH); 7.15–7.18 (m, 2H, Ar—CH); 7.26–7.32 (m, 4H, Ar—CH); 7.81–7.86 (m, 2H, Ar—CH); 8.44 (d, J = 8.0 Hz, ¹H, Ar—CH); 8.62 (d, J = 4.0 Hz, ¹H, Ar—CH). ¹³C NMR (100.56 MHz, CDCl₃, δ p.p.m.): 110.2; 115.1; 120.1; 122.2; 123.8; 124.3; 128.0; 142.2; 148.5; 150.1; 161.4. ¹⁹F NMR (376.266 MHz, CDCl₃, δ p.p.m.): - 115.59.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. ORTEP III diagram of the compound, showing the molecular numbering scheme. Displacement ellipsoids are drawn at 50% probability for all atoms except H.
	Fig. 2. The stacking of the title compound along a-axis with C—H···π type hydrogen-bond interactions.

1-(4-Fluorobenzyl)-2-(pyridin-2-yl)-1H-benzimidazole top

Crystal data top

C₁₉H₁₄FN₃	F(000) = 632
M_r = 303.33	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 0 reflections
a = 4.7363 (5) Å	θ = 2.4–26.7°
b = 15.4102 (17) Å	µ = 0.09 mm⁻¹
c = 20.953 (2) Å	T = 296 K
β = 95.363 (8)°	Stick, orange
V = 1522.6 (3) Å³	0.2 × 0.2 × 0.2 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3133 independent reflections
Radiation source: sealed tube	2355 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 26.7°, θ_min = 2.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −5→5
T_min = 0.984, T_max = 0.984	k = −19→18
13325 measured reflections	l = −26→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: mixed
wR(F²) = 0.103	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0502P)² + 0.1779P] where P = (F_o² + 2F_c²)/3
3133 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₁₄FN₃	V = 1522.6 (3) Å³
M_r = 303.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.7363 (5) Å	µ = 0.09 mm⁻¹
b = 15.4102 (17) Å	T = 296 K
c = 20.953 (2) Å	0.2 × 0.2 × 0.2 mm
β = 95.363 (8)°

Data collection top

Bruker APEXII CCD diffractometer	3133 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2355 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.984	R_int = 0.027
13325 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.103	H-atom parameters constrained
S = 0.93	Δρ_max = 0.14 e Å⁻³
3133 reflections	Δρ_min = −0.17 e Å⁻³
208 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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
N1	0.3612 (2)	0.95634 (7)	0.32306 (5)	0.0598 (3)
N2	0.1288 (2)	1.03423 (7)	0.24400 (6)	0.0669 (3)
C14	0.3980 (3)	0.81860 (8)	0.38380 (6)	0.0574 (3)
C6	0.0419 (3)	1.05982 (8)	0.30241 (7)	0.0629 (3)
C5	0.1882 (3)	1.01343 (8)	0.35209 (7)	0.0607 (3)
C13	0.5514 (3)	0.89547 (9)	0.35911 (7)	0.0661 (4)
H13A	0.6512	0.9256	0.3951	0.079*
H13B	0.6915	0.8750	0.3317	0.079*
C7	0.3181 (3)	0.97274 (8)	0.25818 (7)	0.0602 (3)
C17	0.1266 (4)	0.67652 (9)	0.42898 (8)	0.0785 (4)
F	−0.0115 (3)	0.60689 (7)	0.45190 (6)	0.1195 (4)
C1	−0.1590 (3)	1.12201 (9)	0.31618 (9)	0.0762 (4)
H1	−0.2638	1.1521	0.2836	0.091*
C4	0.1534 (3)	1.02938 (10)	0.41615 (8)	0.0719 (4)
H4	0.2555	0.9989	0.4490	0.086*
C15	0.2114 (3)	0.76997 (10)	0.34407 (7)	0.0736 (4)
H15	0.1766	0.7856	0.3012	0.088*
N3	0.5846 (3)	0.85244 (9)	0.22169 (7)	0.0831 (4)
C19	0.4444 (3)	0.79317 (11)	0.44710 (7)	0.0770 (4)
H19	0.5696	0.8248	0.4749	0.092*
C16	0.0746 (4)	0.69844 (11)	0.36643 (8)	0.0856 (5)
H16	−0.0506	0.6661	0.3391	0.103*
C8	0.4713 (3)	0.93024 (9)	0.20851 (7)	0.0635 (4)
C11	0.7609 (4)	0.85310 (15)	0.11857 (10)	0.0983 (6)
H11	0.8632	0.8251	0.0889	0.118*
C2	−0.1960 (4)	1.13709 (10)	0.37944 (10)	0.0835 (5)
H2	−0.3286	1.1781	0.3897	0.100*
C18	0.3089 (4)	0.72168 (11)	0.47001 (8)	0.0865 (5)
H18	0.3423	0.7050	0.5127	0.104*
C3	−0.0396 (4)	1.09246 (11)	0.42858 (9)	0.0818 (5)
H3	−0.0664	1.1056	0.4709	0.098*
C9	0.4926 (4)	0.97168 (11)	0.15093 (8)	0.0861 (5)
H9	0.4076	1.0254	0.1428	0.103*
C12	0.7260 (4)	0.81593 (13)	0.17637 (10)	0.0989 (6)
H12	0.8060	0.7615	0.1848	0.119*
C10	0.6421 (5)	0.93216 (14)	0.10555 (9)	0.1017 (6)
H10	0.6613	0.9593	0.0665	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0538 (6)	0.0525 (6)	0.0728 (7)	−0.0057 (5)	0.0044 (5)	−0.0023 (5)
N2	0.0652 (7)	0.0542 (6)	0.0812 (8)	−0.0007 (6)	0.0058 (6)	0.0017 (5)
C14	0.0518 (7)	0.0561 (7)	0.0633 (8)	0.0052 (6)	−0.0008 (6)	−0.0061 (6)
C6	0.0578 (7)	0.0471 (7)	0.0847 (9)	−0.0100 (6)	0.0115 (7)	−0.0031 (6)
C5	0.0533 (7)	0.0503 (7)	0.0792 (9)	−0.0144 (6)	0.0099 (6)	−0.0060 (6)
C13	0.0524 (7)	0.0691 (9)	0.0748 (9)	−0.0043 (6)	−0.0048 (6)	−0.0033 (7)
C7	0.0565 (7)	0.0506 (7)	0.0730 (9)	−0.0085 (6)	0.0037 (6)	−0.0018 (6)
C17	0.1041 (12)	0.0522 (8)	0.0826 (10)	0.0003 (8)	0.0259 (9)	−0.0004 (7)
F	0.1701 (11)	0.0738 (6)	0.1201 (9)	−0.0228 (7)	0.0432 (8)	0.0116 (6)
C1	0.0679 (9)	0.0543 (8)	0.1076 (12)	−0.0041 (7)	0.0143 (8)	−0.0013 (8)
C4	0.0684 (9)	0.0682 (9)	0.0801 (10)	−0.0188 (8)	0.0117 (7)	−0.0090 (7)
C15	0.0845 (10)	0.0723 (9)	0.0620 (8)	−0.0157 (8)	−0.0036 (7)	−0.0007 (7)
N3	0.0868 (9)	0.0744 (9)	0.0890 (9)	0.0175 (7)	0.0135 (7)	−0.0045 (7)
C19	0.0821 (10)	0.0777 (10)	0.0679 (9)	0.0005 (8)	−0.0102 (7)	−0.0059 (7)
C16	0.1046 (12)	0.0715 (10)	0.0801 (10)	−0.0271 (9)	0.0046 (9)	−0.0079 (8)
C8	0.0572 (8)	0.0603 (8)	0.0726 (9)	−0.0070 (6)	0.0036 (6)	−0.0066 (7)
C11	0.0899 (12)	0.1126 (15)	0.0951 (13)	0.0017 (12)	0.0224 (10)	−0.0276 (11)
C2	0.0741 (10)	0.0606 (9)	0.1198 (14)	−0.0072 (8)	0.0304 (10)	−0.0160 (9)
C18	0.1154 (13)	0.0768 (11)	0.0666 (9)	0.0084 (10)	0.0046 (9)	0.0092 (8)
C3	0.0811 (11)	0.0713 (10)	0.0966 (12)	−0.0190 (9)	0.0276 (9)	−0.0210 (9)
C9	0.1051 (13)	0.0737 (10)	0.0802 (10)	−0.0003 (9)	0.0134 (9)	0.0007 (8)
C12	0.0997 (13)	0.0955 (13)	0.1023 (13)	0.0277 (11)	0.0142 (11)	−0.0161 (11)
C10	0.1226 (16)	0.1067 (15)	0.0795 (11)	−0.0147 (13)	0.0283 (11)	−0.0091 (10)

Geometric parameters (Å, º) top

N1—C7	1.3790 (17)	C4—H4	0.9300
N1—C5	1.3815 (17)	C15—C16	1.382 (2)
N1—C13	1.4612 (17)	C15—H15	0.9300
N2—C7	1.3192 (17)	N3—C8	1.3319 (19)
N2—C6	1.3845 (18)	N3—C12	1.336 (2)
C14—C15	1.3778 (18)	C19—C18	1.383 (2)
C14—C19	1.381 (2)	C19—H19	0.9300
C14—C13	1.5065 (19)	C16—H16	0.9300
C6—C5	1.393 (2)	C8—C9	1.377 (2)
C6—C1	1.399 (2)	C11—C10	1.359 (3)
C5—C4	1.389 (2)	C11—C12	1.364 (3)
C13—H13A	0.9700	C11—H11	0.9300
C13—H13B	0.9700	C2—C3	1.392 (2)
C7—C8	1.4765 (19)	C2—H2	0.9300
C17—C18	1.353 (2)	C18—H18	0.9300
C17—C16	1.354 (2)	C3—H3	0.9300
C17—F	1.3671 (18)	C9—C10	1.379 (2)
C1—C2	1.373 (2)	C9—H9	0.9300
C1—H1	0.9300	C12—H12	0.9300
C4—C3	1.376 (2)	C10—H10	0.9300

C7—N1—C5	106.14 (11)	C16—C15—H15	119.2
C7—N1—C13	130.90 (12)	C8—N3—C12	116.78 (15)
C5—N1—C13	122.93 (12)	C14—C19—C18	121.46 (14)
C7—N2—C6	104.92 (12)	C14—C19—H19	119.3
C15—C14—C19	117.49 (13)	C18—C19—H19	119.3
C15—C14—C13	121.54 (12)	C17—C16—C15	118.58 (15)
C19—C14—C13	120.95 (12)	C17—C16—H16	120.7
N2—C6—C5	110.25 (12)	C15—C16—H16	120.7
N2—C6—C1	129.90 (14)	N3—C8—C9	122.55 (15)
C5—C6—C1	119.85 (14)	N3—C8—C7	117.91 (13)
N1—C5—C4	131.82 (14)	C9—C8—C7	119.54 (14)
N1—C5—C6	105.78 (12)	C10—C11—C12	118.21 (18)
C4—C5—C6	122.37 (14)	C10—C11—H11	120.9
N1—C13—C14	112.85 (10)	C12—C11—H11	120.9
N1—C13—H13A	109.0	C1—C2—C3	121.54 (15)
C14—C13—H13A	109.0	C1—C2—H2	119.2
N1—C13—H13B	109.0	C3—C2—H2	119.2
C14—C13—H13B	109.0	C17—C18—C19	118.58 (15)
H13A—C13—H13B	107.8	C17—C18—H18	120.7
N2—C7—N1	112.87 (12)	C19—C18—H18	120.7
N2—C7—C8	121.89 (13)	C4—C3—C2	121.72 (16)
N1—C7—C8	125.19 (13)	C4—C3—H3	119.1
C18—C17—C16	122.33 (15)	C2—C3—H3	119.1
C18—C17—F	118.58 (15)	C8—C9—C10	118.93 (17)
C16—C17—F	119.09 (16)	C8—C9—H9	120.5
C2—C1—C6	117.76 (16)	C10—C9—H9	120.5
C2—C1—H1	121.1	N3—C12—C11	124.37 (18)
C6—C1—H1	121.1	N3—C12—H12	117.8
C3—C4—C5	116.67 (16)	C11—C12—H12	117.8
C3—C4—H4	121.7	C11—C10—C9	119.15 (18)
C5—C4—H4	121.7	C11—C10—H10	120.4
C14—C15—C16	121.56 (14)	C9—C10—H10	120.4
C14—C15—H15	119.2

C7—N2—C6—C5	1.27 (14)	C19—C14—C15—C16	0.1 (2)
C7—N2—C6—C1	−178.94 (13)	C13—C14—C15—C16	178.76 (15)
C7—N1—C5—C4	−176.42 (14)	C15—C14—C19—C18	−0.1 (2)
C13—N1—C5—C4	1.7 (2)	C13—C14—C19—C18	−178.73 (14)
C7—N1—C5—C6	1.84 (13)	C18—C17—C16—C15	−0.5 (3)
C13—N1—C5—C6	179.92 (11)	F—C17—C16—C15	178.77 (15)
N2—C6—C5—N1	−1.96 (14)	C14—C15—C16—C17	0.2 (3)
C1—C6—C5—N1	178.22 (11)	C12—N3—C8—C9	0.9 (2)
N2—C6—C5—C4	176.50 (12)	C12—N3—C8—C7	−178.95 (14)
C1—C6—C5—C4	−3.32 (19)	N2—C7—C8—N3	−158.51 (13)
C7—N1—C13—C14	−106.39 (15)	N1—C7—C8—N3	24.2 (2)
C5—N1—C13—C14	76.04 (15)	N2—C7—C8—C9	21.6 (2)
C15—C14—C13—N1	50.84 (18)	N1—C7—C8—C9	−155.75 (14)
C19—C14—C13—N1	−130.59 (14)	C6—C1—C2—C3	0.1 (2)
C6—N2—C7—N1	−0.06 (15)	C16—C17—C18—C19	0.6 (3)
C6—N2—C7—C8	−177.69 (11)	F—C17—C18—C19	−178.74 (15)
C5—N1—C7—N2	−1.16 (14)	C14—C19—C18—C17	−0.2 (3)
C13—N1—C7—N2	−179.03 (12)	C5—C4—C3—C2	1.1 (2)
C5—N1—C7—C8	176.39 (12)	C1—C2—C3—C4	−1.9 (2)
C13—N1—C7—C8	−1.5 (2)	N3—C8—C9—C10	−1.4 (3)
N2—C6—C1—C2	−177.38 (14)	C7—C8—C9—C10	178.46 (15)
C5—C6—C1—C2	2.40 (19)	C8—N3—C12—C11	0.1 (3)
N1—C5—C4—C3	179.55 (13)	C10—C11—C12—N3	−0.7 (3)
C6—C5—C4—C3	1.5 (2)	C12—C11—C10—C9	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.97	2.94	3.486 (2)	117

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.970	2.9345	3.486 (2)	117.17

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer.

References

Ali, M. M., Sato, H., Haga, M., Tanaka, K., Yoshimura, A. & Ohno, T. (1998). Inorg. Chem. 37, 6176–6180. Web of Science CrossRef CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Boca, R., Baran, P., Dlhan, L., Sima, J., Wiesinger, G., Renz, F., El-Ayaan, U. & Linert, W. (1997). Polyhedron, 16, 47–55. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Çelik, Ö., Kasumov, V. T. & Şahin, E. (2009). Acta Cryst. E65, o2786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Çelik, Ö., Ulusoy, M., Taş, E. & Íde, S. (2007). Anal. Sci. 23, 185–186. Google Scholar
Chiswell, B., Lions, F. & Morris, B. S. (1964). Inorg. Chem. 3, 110–114. CrossRef CAS Web of Science Google Scholar
De Castro, B., Freire, C., Domingues, D. & Gomes, J. (1991). Polyhedron, 10, 2541–2549. 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
Haga, M. (1983). Inorg. Chim. Acta, 75, 29–35. CrossRef CAS Web of Science Google Scholar
Harkins, T. R., Walter, J. L., Harris, O. E. & Freiser, H. (1956). J. Am. Chem. Soc. 78, 260–264. CrossRef CAS Web of Science Google Scholar
Hossain, M. D., Haga, M., Gholamkhass, B., Nozaki, K., Tsushima, M., Ikeda, N. & Ohno, T. (2001). Collect Czech. Chem. Commun, 66, 307–337. Web of Science CrossRef CAS Google Scholar
Khalil, M. M. H., Ali, S. A. & Ramadan, R. M. (2001). Spectrochim. Acta Part A, 57, 1017–1024. Web of Science CrossRef Google Scholar
Maekawa, M., Munakata, M., Kuroda-Sowa, T. & Hachiya, K. (1994). Inorg. Chim. Acta, 227, 137–143. CrossRef CAS Web of Science Google Scholar
Sahin, C., Ulusoy, M., Zafer, C., Ozsoy, C., Varlikli, C., Dittrich, T., Cetinkaya, B. & Icli, S. (2010). Dyes Pigm. 84, 88–94. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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