2,4-Bis(4-fluoro­phen­yl)-2,3-dihydro-1H-1,5-benzodiazepine

Baktır, Z.; Akkurt, M.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811015455

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1262-o1263

doi:10.1107/S1600536811015455

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2,4-Bis(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine

Zeliha Baktır,^a Mehmet Akkurt,^a ^* S. Samshuddin,^b B. Narayana ^b and H. S. Yathirajan ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 15 April 2011; accepted 24 April 2011; online 29 April 2011)

In the title compound, C₂₁H₁₆F₂N₂, the seven-membered 1,4-diazepine ring of the benzodiazepine ring system adopts a distorted-boat conformation. The benzene ring of this system makes dihedral angles of 18.6 (2) and 78.8 (2)° with those of two fluorophenyl substituents. In the crystal, inversion dimers linked by two weak C—H⋯F hydrogen bonds generate R₂²(20) ring motifs. There are also weak N—H⋯π and C—H⋯π interactions.

Related literature

For related structures, see: An et al. (2007 ); Bibila Mayaya Bisseyou et al. (2010 ); Harrison et al. (2005 ); Peeters et al. (1997 ). For puckering parameters, see: Cremer & Pople (1975 ). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₁₆F₂N₂
M_r = 334.36
Monoclinic, P 2₁ /n
a = 12.9151 (4) Å
b = 6.0438 (3) Å
c = 21.2851 (7) Å
β = 92.147 (3)°
V = 1660.27 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ) T_min = 0.981, T_max = 0.981
3413 measured reflections
3413 independent reflections
1226 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.151
S = 1.04
3413 reflections
233 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the benzene rings of the two fluorophenyl substituents (C10–C15 and C16–C21, respectively).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F1ⁱ	0.93	2.54	3.469 (6)	175
N1—H1N⋯Cg2ⁱ	0.86 (3)	2.82 (5)	3.601 (4)	151 (4)
C2—H2⋯Cg1ⁱⁱ	0.93	2.89	3.640 (5)	138
C11—H11⋯Cg2	0.93	2.79	3.494 (5)	134
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015455/hb5848sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015455/hb5848Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015455/hb5848Isup3.cml

checkCIF report

Comment top

The crystal structures of some 1,5-benzodiazepines, viz., 2-[2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]phenol (Bibila Mayaya Bisseyou et al., 2010), 1-(2-bromo-5-methoxyphenyl)-8-chloro-6-(2-fluorophenyl)-4H-1,2,4-triazolo[4,3-a][1,4] benzodiazepine (Harrison et al., 2005), 5-(4-fluorophenyl)-1,8-dimethyl-2-(p-toluoylaminomethyl)-2,3-dihydro-1H-1,4-benzodiazepine monohydrate (Peeters et al., 1997) and 2,4-bis(4-chlorophenyl)-2-methyl-2,3-dihydro-1H-1,5-benzodiazepine (An et al., 2007) have been reported. In continuation of this work, the title compound, (I), is synthesized and its crystal structure is reported here.

The seven-membered 1,4-diazepine ring (C1/C6–C9/N1/N2) of the benzodiazepine ring system (C1–C9/N1/N2) adopts a distorted-boat conformation [the puckering parameters (Cremer & Pople, 1975) for this eleven-membered ring system are: Q₂ = 0.917 (4) Å, Q₃ = 0.155 (4) Å, ϕ₂ = 16.6 (3)° and ϕ₃ = 92.6 (17)°] as shown in Fig. 1. The benzene ring (C1–C6) of this system forms dihedral angles of 18.6 (2)° and 78.8 (2)° with the benzene rings (C10–C15 and C16–C21) of two fluorophenyl fragments, respectively which make a dihedral angle of 62.1 (2)° with each other.

In the crystal, the two weak C—H···F hydrogen bonds link pairs of inversion-related molecules to form cyclic centrosymmetric dimers containing the R²₂(20) ring motif (Bernstein et al., 1995; Table 1, Fig. 2). In addtion, three C—H···π interactions are observed (Table 1).

Related literature top

For related structures, see: An et al. (2007); Bibila Mayaya Bisseyou et al. (2010); Harrison et al. (2005); Peeters et al. (1997). For puckering parameters, see: Cremer & Pople (1975). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

To a solution of 4,4'-difluoro chalcone (2.44 g, 0.01 mol) in ethanol (30 ml) a few drops of piperidine and 1, 2-diaminobenzene (1.08 g, 01 mol) were added. The mixture was heated under reflux for 10 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Pale yellow blocks of (I) were grown from DMF by slow evaporation method in 66% yield (m. p.: 409 K).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the b axis. Hydrogen bonds are shown as dotted lines.

2,4-Bis(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine top

Crystal data top

C₂₁H₁₆F₂N₂	F(000) = 696
M_r = 334.36	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1691 reflections
a = 12.9151 (4) Å	θ = 2.5–26.3°
b = 6.0438 (3) Å	µ = 0.10 mm⁻¹
c = 21.2851 (7) Å	T = 294 K
β = 92.147 (3)°	Block, pale yellow
V = 1660.27 (11) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3413 independent reflections
Radiation source: Sealed Tube	1226 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.000
Detector resolution: 10.0000 pixels mm^-1	θ_max = 26.5°, θ_min = 3.2°
dtprofit.ref scans	h = −16→16
Absorption correction: part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995); Cubic fit to sinθ/λ, 24 parameters]	k = 0→7
T_min = 0.981, T_max = 0.981	l = 0→26
3413 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.P)² + 1.2828P] where P = (F_o² + 2F_c²)/3
3413 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.16 e Å⁻³
2 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₁₆F₂N₂	V = 1660.27 (11) Å³
M_r = 334.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.9151 (4) Å	µ = 0.10 mm⁻¹
b = 6.0438 (3) Å	T = 294 K
c = 21.2851 (7) Å	0.20 × 0.20 × 0.20 mm
β = 92.147 (3)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3413 independent reflections
Absorption correction: part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995); Cubic fit to sinθ/λ, 24 parameters]	1226 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.981	R_int = 0.000
3413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	2 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.16 e Å⁻³
3413 reflections	Δρ_min = −0.18 e Å⁻³
233 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	0.2985 (2)	0.5093 (5)	0.38988 (13)	0.1156 (16)
F2	0.6025 (2)	−0.0519 (5)	0.58369 (17)	0.1365 (18)
N1	−0.0014 (3)	0.2319 (7)	0.60658 (19)	0.0764 (17)
N2	0.1477 (3)	−0.0519 (6)	0.67436 (16)	0.0667 (16)
C1	0.0446 (4)	−0.0259 (7)	0.6923 (2)	0.0649 (17)
C2	0.0114 (4)	−0.1609 (7)	0.7400 (2)	0.0747 (19)
C3	−0.0881 (4)	−0.1566 (8)	0.7601 (2)	0.084 (2)
C4	−0.1587 (4)	−0.0156 (9)	0.7299 (2)	0.090 (2)
C5	−0.1280 (4)	0.1161 (8)	0.6815 (2)	0.083 (2)
C6	−0.0273 (4)	0.1150 (7)	0.6613 (2)	0.0669 (17)
C7	0.0768 (4)	0.4074 (7)	0.6097 (2)	0.0674 (17)
C8	0.1593 (3)	0.3499 (7)	0.66113 (19)	0.0675 (17)
C9	0.2006 (3)	0.1161 (7)	0.6576 (2)	0.0635 (17)
C10	0.3074 (3)	0.0767 (7)	0.6375 (2)	0.0652 (17)
C11	0.3591 (4)	0.2231 (8)	0.6009 (2)	0.080 (2)
C12	0.4584 (4)	0.1818 (9)	0.5813 (2)	0.095 (3)
C13	0.5044 (4)	−0.0120 (10)	0.6017 (3)	0.094 (3)
C14	0.4580 (4)	−0.1612 (8)	0.6392 (2)	0.085 (2)
C15	0.3579 (4)	−0.1181 (7)	0.6567 (2)	0.0735 (17)
C16	0.1258 (3)	0.4366 (7)	0.5464 (2)	0.0628 (17)
C17	0.1274 (3)	0.2722 (7)	0.5013 (2)	0.0710 (17)
C18	0.1843 (4)	0.2974 (9)	0.4478 (2)	0.083 (2)
C19	0.2394 (4)	0.4894 (10)	0.4416 (2)	0.081 (2)
C20	0.2382 (4)	0.6561 (8)	0.4837 (2)	0.080 (2)
C21	0.1800 (3)	0.6298 (7)	0.5363 (2)	0.0721 (17)
H1N	−0.060 (2)	0.265 (10)	0.588 (2)	0.1640*
H2	0.05840	−0.25840	0.75920	0.0900*
H3	−0.10780	−0.24590	0.79310	0.1010*
H4	−0.22690	−0.01050	0.74250	0.1080*
H5	−0.17630	0.20920	0.66170	0.1000*
H7	0.048 (4)	0.552 (4)	0.621 (2)	0.1640*
H8A	0.21670	0.45220	0.65810	0.0810*
H8B	0.12960	0.37130	0.70190	0.0810*
H11	0.32650	0.35440	0.58870	0.0960*
H12	0.49230	0.28040	0.55560	0.1140*
H14	0.49250	−0.28860	0.65270	0.1020*
H15	0.32380	−0.21960	0.68140	0.0880*
H17	0.08980	0.14290	0.50700	0.0850*
H18	0.18500	0.18780	0.41710	0.0990*
H20	0.27570	0.78520	0.47760	0.0960*
H21	0.17710	0.74420	0.56540	0.0860*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.117 (3)	0.135 (3)	0.098 (2)	0.027 (2)	0.0457 (19)	0.034 (2)
F2	0.080 (2)	0.133 (3)	0.199 (4)	0.019 (2)	0.040 (2)	0.037 (3)
N1	0.065 (3)	0.093 (3)	0.071 (3)	−0.011 (2)	0.002 (2)	0.014 (2)
N2	0.063 (3)	0.064 (2)	0.073 (3)	0.001 (2)	0.003 (2)	0.001 (2)
C1	0.065 (3)	0.066 (3)	0.064 (3)	−0.005 (3)	0.006 (2)	0.001 (2)
C2	0.078 (4)	0.070 (3)	0.076 (3)	0.000 (3)	0.002 (3)	0.003 (3)
C3	0.088 (4)	0.088 (4)	0.077 (4)	0.001 (3)	0.020 (3)	0.014 (3)
C4	0.073 (4)	0.109 (4)	0.090 (4)	0.005 (3)	0.015 (3)	0.011 (3)
C5	0.069 (3)	0.098 (4)	0.083 (4)	0.009 (3)	0.013 (3)	0.012 (3)
C6	0.066 (3)	0.072 (3)	0.063 (3)	0.001 (3)	0.008 (2)	0.002 (2)
C7	0.069 (3)	0.069 (3)	0.064 (3)	0.004 (3)	0.000 (2)	0.004 (3)
C8	0.072 (3)	0.064 (3)	0.066 (3)	−0.001 (2)	−0.003 (2)	−0.003 (2)
C9	0.064 (3)	0.061 (3)	0.065 (3)	0.005 (2)	−0.004 (2)	0.000 (2)
C10	0.062 (3)	0.067 (3)	0.066 (3)	−0.004 (3)	−0.006 (2)	0.000 (2)
C11	0.062 (3)	0.082 (4)	0.096 (4)	0.001 (3)	0.000 (3)	0.015 (3)
C12	0.071 (4)	0.102 (4)	0.113 (5)	0.003 (3)	0.013 (3)	0.031 (3)
C13	0.056 (3)	0.105 (5)	0.123 (5)	0.012 (3)	0.015 (3)	0.010 (4)
C14	0.067 (4)	0.078 (4)	0.109 (4)	0.005 (3)	0.003 (3)	0.010 (3)
C15	0.069 (3)	0.067 (3)	0.084 (3)	−0.007 (3)	−0.002 (3)	−0.001 (3)
C16	0.061 (3)	0.061 (3)	0.066 (3)	0.004 (2)	−0.004 (2)	0.002 (2)
C17	0.073 (3)	0.068 (3)	0.072 (3)	0.003 (3)	0.003 (3)	0.001 (3)
C18	0.091 (4)	0.084 (4)	0.074 (4)	0.016 (3)	0.007 (3)	−0.006 (3)
C19	0.078 (4)	0.099 (4)	0.067 (3)	0.020 (3)	0.017 (3)	0.023 (3)
C20	0.080 (4)	0.074 (4)	0.085 (4)	0.006 (3)	0.006 (3)	0.017 (3)
C21	0.077 (3)	0.068 (3)	0.071 (3)	0.002 (3)	−0.002 (3)	0.001 (3)

Geometric parameters (Å, º) top

F1—C19	1.368 (5)	C14—C15	1.384 (7)
F2—C13	1.359 (6)	C16—C21	1.382 (6)
N1—C6	1.413 (6)	C16—C17	1.382 (6)
N1—C7	1.464 (6)	C17—C18	1.387 (6)
N2—C1	1.408 (6)	C18—C19	1.370 (8)
N2—C9	1.282 (6)	C19—C20	1.349 (7)
N1—H1N	0.86 (3)	C20—C21	1.381 (6)
C1—C6	1.406 (7)	C2—H2	0.9300
C1—C2	1.383 (6)	C3—H3	0.9300
C2—C3	1.370 (7)	C4—H4	0.9300
C3—C4	1.388 (7)	C5—H5	0.9300
C4—C5	1.372 (7)	C7—H7	0.98 (3)
C5—C6	1.385 (7)	C8—H8A	0.9700
C7—C8	1.539 (6)	C8—H8B	0.9700
C7—C16	1.520 (6)	C11—H11	0.9300
C8—C9	1.513 (6)	C12—H12	0.9300
C9—C10	1.479 (6)	C14—H14	0.9300
C10—C11	1.369 (6)	C15—H15	0.9300
C10—C15	1.400 (6)	C17—H17	0.9300
C11—C12	1.386 (7)	C18—H18	0.9300
C12—C13	1.376 (8)	C20—H20	0.9300
C13—C14	1.358 (8)	C21—H21	0.9300

C6—N1—C7	120.6 (4)	F1—C19—C18	117.4 (4)
C1—N2—C9	120.4 (4)	C18—C19—C20	123.3 (4)
C7—N1—H1N	116 (4)	C19—C20—C21	118.2 (5)
C6—N1—H1N	105 (3)	C16—C21—C20	121.2 (4)
N2—C1—C6	123.7 (4)	C1—C2—H2	119.00
C2—C1—C6	119.0 (5)	C3—C2—H2	119.00
N2—C1—C2	117.1 (4)	C2—C3—H3	121.00
C1—C2—C3	122.6 (4)	C4—C3—H3	121.00
C2—C3—C4	118.3 (4)	C3—C4—H4	120.00
C3—C4—C5	120.0 (5)	C5—C4—H4	120.00
C4—C5—C6	122.1 (5)	C4—C5—H5	119.00
C1—C6—C5	117.9 (4)	C6—C5—H5	119.00
N1—C6—C1	121.1 (4)	N1—C7—H7	113 (3)
N1—C6—C5	120.5 (4)	C8—C7—H7	107 (3)
N1—C7—C16	110.7 (4)	C16—C7—H7	107 (2)
N1—C7—C8	109.1 (3)	C7—C8—H8A	109.00
C8—C7—C16	110.9 (4)	C7—C8—H8B	109.00
C7—C8—C9	114.3 (3)	C9—C8—H8A	109.00
N2—C9—C8	122.2 (4)	C9—C8—H8B	109.00
C8—C9—C10	119.9 (4)	H8A—C8—H8B	108.00
N2—C9—C10	117.8 (4)	C10—C11—H11	119.00
C9—C10—C15	118.7 (4)	C12—C11—H11	119.00
C9—C10—C11	122.7 (4)	C11—C12—H12	122.00
C11—C10—C15	118.6 (4)	C13—C12—H12	122.00
C10—C11—C12	122.1 (4)	C13—C14—H14	121.00
C11—C12—C13	116.9 (5)	C15—C14—H14	121.00
C12—C13—C14	123.8 (5)	C10—C15—H15	120.00
F2—C13—C14	119.0 (5)	C14—C15—H15	120.00
F2—C13—C12	117.3 (5)	C16—C17—H17	119.00
C13—C14—C15	118.1 (5)	C18—C17—H17	120.00
C10—C15—C14	120.7 (4)	C17—C18—H18	121.00
C17—C16—C21	118.6 (4)	C19—C18—H18	121.00
C7—C16—C17	123.3 (4)	C19—C20—H20	121.00
C7—C16—C21	117.8 (4)	C21—C20—H20	121.00
C16—C17—C18	120.9 (4)	C16—C21—H21	119.00
C17—C18—C19	117.7 (4)	C20—C21—H21	119.00
F1—C19—C20	119.3 (5)

C6—N1—C7—C8	32.4 (5)	C7—C8—C9—N2	−74.6 (5)
C6—N1—C7—C16	154.7 (4)	N2—C9—C10—C11	159.0 (4)
C7—N1—C6—C1	−67.0 (6)	N2—C9—C10—C15	−21.1 (6)
C7—N1—C6—C5	120.7 (5)	C8—C9—C10—C11	−24.2 (6)
C9—N2—C1—C6	40.9 (6)	C8—C9—C10—C15	155.7 (4)
C9—N2—C1—C2	−144.4 (4)	C9—C10—C11—C12	−178.6 (4)
C1—N2—C9—C8	5.1 (6)	C15—C10—C11—C12	1.5 (7)
C1—N2—C9—C10	−178.2 (4)	C9—C10—C15—C14	−179.7 (4)
N2—C1—C6—C5	176.5 (4)	C11—C10—C15—C14	0.2 (7)
N2—C1—C2—C3	−177.7 (4)	C10—C11—C12—C13	−1.6 (7)
C6—C1—C2—C3	−2.7 (7)	C11—C12—C13—F2	−178.8 (5)
N2—C1—C6—N1	3.9 (7)	C11—C12—C13—C14	0.1 (8)
C2—C1—C6—N1	−170.7 (4)	F2—C13—C14—C15	−179.6 (5)
C2—C1—C6—C5	1.8 (6)	C12—C13—C14—C15	1.5 (8)
C1—C2—C3—C4	2.0 (7)	C13—C14—C15—C10	−1.6 (7)
C2—C3—C4—C5	−0.5 (7)	C7—C16—C17—C18	−171.8 (4)
C3—C4—C5—C6	−0.3 (7)	C21—C16—C17—C18	1.7 (6)
C4—C5—C6—C1	−0.4 (7)	C7—C16—C21—C20	171.2 (4)
C4—C5—C6—N1	172.2 (4)	C17—C16—C21—C20	−2.6 (6)
N1—C7—C8—C9	48.6 (5)	C16—C17—C18—C19	0.6 (7)
N1—C7—C16—C21	163.2 (4)	C17—C18—C19—F1	177.5 (4)
C8—C7—C16—C17	97.9 (5)	C17—C18—C19—C20	−2.2 (8)
C8—C7—C16—C21	−75.6 (5)	F1—C19—C20—C21	−178.4 (4)
N1—C7—C16—C17	−23.3 (6)	C18—C19—C20—C21	1.3 (8)
C16—C7—C8—C9	−73.5 (4)	C19—C20—C21—C16	1.2 (7)
C7—C8—C9—C10	108.7 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the benzene rings of the two fluorophenyl substituents (C10–C15 and C16–C21, respectively).

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1ⁱ	0.93	2.54	3.469 (6)	175
N1—H1N···Cg2ⁱ	0.86 (3)	2.82 (5)	3.601 (4)	151 (4)
C2—H2···Cg1ⁱⁱ	0.93	2.89	3.640 (5)	138
C11—H11···Cg2	0.93	2.79	3.494 (5)	134

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆F₂N₂
M_r	334.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	12.9151 (4), 6.0438 (3), 21.2851 (7)
β (°)	92.147 (3)
V (Å³)	1660.27 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995); Cubic fit to sinθ/λ, 24 parameters]
T_min, T_max	0.981, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	3413, 3413, 1226
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.151, 1.04
No. of reflections	3413
No. of parameters	233
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)	0.16, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the benzene rings of the two fluorophenyl substituents (C10–C15 and C16–C21, respectively).

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1ⁱ	0.93	2.54	3.469 (6)	175
N1—H1N···Cg2ⁱ	0.86 (3)	2.82 (5)	3.601 (4)	151 (4)
C2—H2···Cg1ⁱⁱ	0.93	2.89	3.640 (5)	138
C11—H11···Cg2	0.93	2.79	3.494 (5)	134

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

Acknowledgements

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey for the research grant FBD-10–2949, and for support of the data collection at Atatürk University, Turkey. SS and BN thank Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave.

References

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Volume 67| Part 5| May 2011| Pages o1262-o1263

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