1-(3,5-Dimethyl­phen­yl)-2-(4-fluoro­phen­yl)-1H-phenanthro[9,10-d]imidazole

Sathishkumar, R.; Mohandas, T.; Sakthivel, P.; Jayabharathi, J.

doi:10.1107/S1600536813003486

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o367

doi:10.1107/S1600536813003486

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1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-1H-phenanthro[9,10-d]imidazole

R. Sathishkumar,^a T. Mohandas,^b P. Sakthivel ^c ^* and J. Jayabharathi ^a

^aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, ^bShri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India, and ^cDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

(Received 4 January 2013; accepted 4 February 2013; online 9 February 2013)

In the title compound, C₂₉H₂₁FN₂, the phenanthro tricyclic ring system is essentially planar with a maximum deviation of 0.030 (2) Å and makes dihedral angles between of 77.96 (6) and 37.18 (7)° with the dimethylphenyl and fluorophenyl rings, respectively. The crystal packing features weak C—H⋯π interactions involving the dimethylphenyl and other phenyl rings.

Related literature

For the use of phenanthroline derivatives in the construction of molecular devices, see: Yamada et al. (1992 ). For the biological activity of imidazole, see: Nebert & Gonzalez (1987 ). For related metallo-supramolecular chemistry, see: Lehn (1996 ). For applications of complexes based on phenanthroline, see: Walters et al. (2000 ); Peng et al. (1997 ); Hara et al. (2001 ).

Experimental

Crystal data

C₂₉H₂₁FN₂
M_r = 416.48
Monoclinic, P 2₁ /n
a = 8.5680 (2) Å
b = 10.6070 (3) Å
c = 23.6900 (6) Å
β = 93.899 (1)°
V = 2147.98 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.952, T_max = 0.995
19934 measured reflections
3777 independent reflections
2957 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.02
3777 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7/C8/C13/C14/C19/C20 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg1	0.93	2.97	3.84	156
C6—H6⋯Cg2ⁱ	0.93	2.97	3.70	155
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813003486/rk2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003486/rk2393Isup2.hkl

checkCIF report

Comment top

The derivatives of phenanthroline, which have excellent hole blocking and electron transporting properties, are likely to have interesting value in the construction of molecular devices (Yamada et al., 1992).

Indeed, various imidazole derivatives have shown a broad range of bioactivities, such as antineoplastic, immunosuppressive and anti-inflammatory activities (Nebert et al., 1987).

The large variety of complexes based on phenanthroline and its derivatives allows the formation of many different molecular systems with various applications ranging from metallo-supramolecular chemistry (Lehn et al., 1996), metal sensors (Walters et al., 2000), molecular electronics (Peng et al., 1997) and photo sensitizers (Hara et al., 2001).

The molecular structure is shown in Fig.1. The phenanthro tricycle is essentialy planar. The dihedral angles between phenanthro tricycle to the dimethylphenyl is 77.96 (6)° and to that of fluorophenyl ring is 37.18 (7)° respectively.

Further the crystal is stabilized by intermolecular C–H···π interactions (Table 1), where Cg1 is the centre of gravity of C7/C8/C13/C14/C19/C20 and Cg2 is the centre of gravity of (C8-C13). The symmetry code are: (i) 1/2-x, 1/2+y, 1/2-z.

Related literature top

For the use of phenanthroline derivatives in the construction of molecular devices, see: Yamada et al. (1992). For the biological activity of imidazole, see: Nebert & Gonzalez (1987). For related metallo-supramolecular chemistry, see: Lehn (1996). For applications of complexes based on phenanthroline, see: Walters et al. (2000); Peng et al. (1997); Hara et al. (2001).

Experimental top

A mixture of phenanthrene-9,10-dione (1.0 g, 4.8 mmol), ammonium acetate (1.48 g, 19.2 mmol), 4-fluorobenzaldehyde (0.62 g, 4.8 mmol) and 3,5-dimethyl aniline (3.82 g, 24 mmol) have been refluxed in ethanol (20 ml) at 353 K. The reaction was monitored by TLC and purified by column chromatography using petroleum ether : ethyl acetate (9:1) as the eluent. Yield: 0.78 g (50%). The compound was dissolved in DMSO and allowed to slow evaporation and single crystals were grown within a period of one week.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as spheres with arbitrary radius.
	Fig. 2. A packing diagram of the title compound. The molecules are connected by C–H···π interactions as shown by dashed line.

1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-1H-phenanthro[9,10-d]imidazole top

Crystal data top

C₂₉H₂₁FN₂	F(000) = 872
M_r = 416.48	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6884 reflections
a = 8.5680 (2) Å	θ = 2.6–25.8°
b = 10.6070 (3) Å	µ = 0.08 mm⁻¹
c = 23.6900 (6) Å	T = 295 K
β = 93.899 (1)°	Block, colourless
V = 2147.98 (10) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3777 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω– and ϕ–scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.952, T_max = 0.995	k = −12→12
19934 measured reflections	l = −28→28

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.047P)² + 0.6584P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3777 reflections	Δρ_max = 0.24 e Å⁻³
292 parameters	Δρ_min = −0.15 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: 0.0229 (14)

Crystal data top

C₂₉H₂₁FN₂	V = 2147.98 (10) Å³
M_r = 416.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5680 (2) Å	µ = 0.08 mm⁻¹
b = 10.6070 (3) Å	T = 295 K
c = 23.6900 (6) Å	0.30 × 0.20 × 0.20 mm
β = 93.899 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3777 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2957 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.995	R_int = 0.034
19934 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
3777 reflections	Δρ_min = −0.15 e Å⁻³
292 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > σ(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
F1	−0.12516 (16)	−0.11339 (12)	0.46971 (5)	0.0814 (5)
N1	−0.17180 (15)	0.00029 (12)	0.20526 (5)	0.0432 (4)
N2	−0.01474 (14)	0.16068 (12)	0.23196 (5)	0.0397 (4)
C1	0.13686 (19)	0.43494 (15)	0.31531 (7)	0.0426 (5)
C2	0.03897 (18)	0.35869 (15)	0.28130 (7)	0.0417 (5)
C3	0.08624 (17)	0.23859 (14)	0.26818 (6)	0.0384 (5)
C4	0.22859 (18)	0.19160 (15)	0.28854 (7)	0.0428 (5)
C5	0.32914 (18)	0.26633 (16)	0.32246 (7)	0.0482 (6)
C6	0.2809 (2)	0.38706 (16)	0.33513 (7)	0.0486 (6)
C7	−0.03496 (17)	0.16561 (14)	0.17341 (6)	0.0385 (5)
C8	0.02988 (18)	0.24785 (15)	0.13278 (7)	0.0424 (5)
C9	0.1372 (2)	0.34535 (16)	0.14610 (8)	0.0520 (6)
C10	0.1931 (2)	0.41945 (19)	0.10496 (9)	0.0624 (7)
C11	0.1435 (3)	0.3995 (2)	0.04904 (9)	0.0740 (8)
C12	0.0414 (3)	0.3043 (2)	0.03479 (8)	0.0692 (8)
C13	−0.0186 (2)	0.22404 (17)	0.07527 (7)	0.0504 (6)
C14	−0.1241 (2)	0.12002 (17)	0.05928 (7)	0.0505 (6)
C15	−0.1728 (3)	0.0935 (2)	0.00278 (8)	0.0742 (8)
C16	−0.2694 (3)	−0.0054 (3)	−0.01118 (9)	0.0833 (9)
C17	−0.3242 (3)	−0.0829 (2)	0.02974 (9)	0.0705 (8)
C18	−0.2803 (2)	−0.06043 (17)	0.08542 (8)	0.0537 (6)
C19	−0.18058 (18)	0.04040 (16)	0.10068 (7)	0.0442 (5)
C20	−0.13220 (17)	0.06682 (14)	0.15854 (6)	0.0395 (5)
C21	−0.09957 (18)	0.05819 (14)	0.24857 (7)	0.0401 (5)
C22	−0.10644 (18)	0.01699 (15)	0.30742 (7)	0.0412 (5)
C23	−0.1144 (2)	−0.11111 (16)	0.31864 (7)	0.0507 (6)
C24	−0.1214 (2)	−0.15484 (17)	0.37296 (8)	0.0551 (6)
C25	−0.1211 (2)	−0.07015 (18)	0.41601 (7)	0.0542 (6)
C26	−0.1164 (3)	0.05626 (19)	0.40719 (8)	0.0627 (7)
C27	−0.1093 (2)	0.09943 (17)	0.35261 (8)	0.0547 (6)
C28	0.4870 (2)	0.2170 (2)	0.34406 (10)	0.0739 (8)
C29	0.0858 (2)	0.56524 (16)	0.33040 (8)	0.0557 (6)
H2	−0.05829	0.38834	0.26736	0.0501*
H4	0.25741	0.10985	0.27959	0.0514*
H6	0.34764	0.43796	0.35778	0.0584*
H9	0.17076	0.35964	0.18372	0.0624*
H10	0.26440	0.48327	0.11457	0.0749*
H11	0.17975	0.45104	0.02102	0.0888*
H12	0.01026	0.29201	−0.00318	0.0830*
H15	−0.13831	0.14452	−0.02578	0.0890*
H16	−0.29900	−0.02076	−0.04906	0.0999*
H17	−0.39033	−0.14989	0.01960	0.0846*
H18	−0.31691	−0.11232	0.11328	0.0644*
H23	−0.11507	−0.16832	0.28888	0.0608*
H24	−0.12626	−0.24089	0.38017	0.0661*
H26	−0.11785	0.11237	0.43731	0.0753*
H27	−0.10636	0.18578	0.34598	0.0656*
H28A	0.49953	0.22771	0.38435	0.1108*
H28B	0.49460	0.12914	0.33495	0.1108*
H28C	0.56759	0.26283	0.32662	0.1108*
H29A	0.02493	0.56122	0.36291	0.0836*
H29B	0.17619	0.61712	0.33882	0.0836*
H29C	0.02357	0.60076	0.29911	0.0836*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1151 (10)	0.0821 (9)	0.0484 (7)	−0.0124 (7)	0.0160 (6)	0.0106 (6)
N1	0.0415 (7)	0.0419 (8)	0.0456 (8)	−0.0017 (6)	−0.0016 (6)	−0.0019 (6)
N2	0.0403 (7)	0.0382 (7)	0.0399 (7)	−0.0021 (6)	−0.0023 (6)	−0.0012 (6)
C1	0.0456 (9)	0.0402 (9)	0.0425 (9)	−0.0079 (7)	0.0076 (7)	0.0003 (7)
C2	0.0367 (8)	0.0415 (9)	0.0468 (9)	−0.0007 (7)	0.0021 (7)	0.0017 (7)
C3	0.0359 (8)	0.0394 (9)	0.0396 (8)	−0.0042 (7)	0.0011 (6)	0.0001 (7)
C4	0.0408 (9)	0.0404 (9)	0.0474 (9)	0.0003 (7)	0.0042 (7)	0.0017 (7)
C5	0.0386 (9)	0.0512 (10)	0.0539 (10)	−0.0057 (8)	−0.0027 (8)	0.0066 (8)
C6	0.0463 (9)	0.0503 (10)	0.0486 (10)	−0.0156 (8)	−0.0018 (8)	−0.0014 (8)
C7	0.0358 (8)	0.0382 (9)	0.0412 (9)	0.0061 (7)	−0.0005 (7)	−0.0004 (7)
C8	0.0387 (8)	0.0423 (9)	0.0464 (9)	0.0077 (7)	0.0049 (7)	0.0021 (7)
C9	0.0512 (10)	0.0495 (10)	0.0559 (11)	−0.0006 (8)	0.0079 (8)	0.0031 (8)
C10	0.0623 (12)	0.0551 (12)	0.0715 (14)	−0.0063 (9)	0.0171 (10)	0.0046 (10)
C11	0.0864 (16)	0.0722 (14)	0.0662 (14)	−0.0087 (12)	0.0262 (12)	0.0136 (11)
C12	0.0818 (14)	0.0790 (14)	0.0478 (11)	−0.0010 (12)	0.0121 (10)	0.0069 (10)
C13	0.0497 (10)	0.0559 (11)	0.0463 (10)	0.0089 (8)	0.0084 (8)	0.0036 (8)
C14	0.0500 (10)	0.0582 (11)	0.0430 (9)	0.0104 (8)	0.0017 (8)	−0.0030 (8)
C15	0.0824 (15)	0.0948 (17)	0.0446 (11)	−0.0068 (13)	−0.0011 (10)	−0.0024 (11)
C16	0.0932 (17)	0.1064 (19)	0.0476 (12)	−0.0068 (15)	−0.0140 (11)	−0.0170 (12)
C17	0.0713 (13)	0.0731 (14)	0.0644 (13)	−0.0016 (11)	−0.0145 (11)	−0.0180 (11)
C18	0.0517 (10)	0.0528 (11)	0.0547 (11)	0.0040 (8)	−0.0091 (8)	−0.0088 (8)
C19	0.0400 (9)	0.0462 (9)	0.0456 (9)	0.0095 (7)	−0.0025 (7)	−0.0069 (8)
C20	0.0357 (8)	0.0397 (9)	0.0426 (9)	0.0051 (7)	−0.0012 (7)	−0.0015 (7)
C21	0.0368 (8)	0.0377 (9)	0.0454 (9)	−0.0010 (7)	0.0000 (7)	−0.0011 (7)
C22	0.0364 (8)	0.0428 (9)	0.0443 (9)	−0.0022 (7)	0.0023 (7)	−0.0006 (7)
C23	0.0621 (11)	0.0431 (10)	0.0467 (10)	−0.0068 (8)	0.0022 (8)	−0.0040 (8)
C24	0.0676 (12)	0.0421 (10)	0.0558 (11)	−0.0066 (9)	0.0059 (9)	0.0051 (8)
C25	0.0586 (11)	0.0606 (12)	0.0441 (10)	−0.0065 (9)	0.0093 (8)	0.0051 (9)
C26	0.0854 (14)	0.0546 (12)	0.0503 (11)	−0.0078 (10)	0.0199 (10)	−0.0104 (9)
C27	0.0706 (12)	0.0402 (10)	0.0548 (11)	−0.0014 (9)	0.0160 (9)	−0.0023 (8)
C28	0.0490 (11)	0.0698 (14)	0.0991 (17)	−0.0021 (10)	−0.0219 (11)	0.0089 (12)
C29	0.0626 (12)	0.0446 (10)	0.0609 (11)	−0.0092 (9)	0.0110 (9)	−0.0070 (8)

Geometric parameters (Å, º) top

F1—C25	1.355 (2)	C19—C20	1.433 (2)
N1—C20	1.3745 (19)	C21—C22	1.466 (2)
N1—C21	1.314 (2)	C22—C23	1.387 (2)
N2—C3	1.4376 (19)	C22—C27	1.384 (2)
N2—C7	1.3871 (18)	C23—C24	1.373 (3)
N2—C21	1.380 (2)	C24—C25	1.359 (3)
C1—C2	1.384 (2)	C25—C26	1.358 (3)
C1—C6	1.387 (2)	C26—C27	1.377 (3)
C1—C29	1.500 (2)	C2—H2	0.9300
C2—C3	1.379 (2)	C4—H4	0.9300
C3—C4	1.374 (2)	C6—H6	0.9300
C4—C5	1.386 (2)	C9—H9	0.9300
C5—C6	1.385 (2)	C10—H10	0.9300
C5—C28	1.507 (2)	C11—H11	0.9300
C7—C8	1.438 (2)	C12—H12	0.9300
C7—C20	1.370 (2)	C15—H15	0.9300
C8—C9	1.405 (2)	C16—H16	0.9300
C8—C13	1.420 (2)	C17—H17	0.9300
C9—C10	1.364 (3)	C18—H18	0.9300
C10—C11	1.380 (3)	C23—H23	0.9300
C11—C12	1.363 (3)	C24—H24	0.9300
C12—C13	1.406 (3)	C26—H26	0.9300
C13—C14	1.460 (2)	C27—H27	0.9300
C14—C15	1.403 (3)	C28—H28A	0.9600
C14—C19	1.405 (2)	C28—H28B	0.9600
C15—C16	1.363 (4)	C28—H28C	0.9600
C16—C17	1.378 (3)	C29—H29A	0.9600
C17—C18	1.368 (3)	C29—H29B	0.9600
C18—C19	1.401 (2)	C29—H29C	0.9600

C20—N1—C21	105.06 (13)	C23—C24—C25	118.82 (17)
C3—N2—C7	127.18 (12)	F1—C25—C24	118.82 (17)
C3—N2—C21	126.16 (12)	F1—C25—C26	118.79 (16)
C7—N2—C21	106.41 (12)	C24—C25—C26	122.40 (17)
C2—C1—C6	118.25 (15)	C25—C26—C27	118.46 (17)
C2—C1—C29	120.14 (15)	C22—C27—C26	121.37 (17)
C6—C1—C29	121.60 (15)	C1—C2—H2	120.00
C1—C2—C3	119.71 (14)	C3—C2—H2	120.00
N2—C3—C2	119.45 (13)	C3—C4—H4	120.00
N2—C3—C4	119.00 (13)	C5—C4—H4	120.00
C2—C3—C4	121.56 (14)	C1—C6—H6	119.00
C3—C4—C5	119.85 (15)	C5—C6—H6	119.00
C4—C5—C6	118.13 (15)	C8—C9—H9	119.00
C4—C5—C28	120.42 (16)	C10—C9—H9	119.00
C6—C5—C28	121.45 (16)	C9—C10—H10	120.00
C1—C6—C5	122.49 (15)	C11—C10—H10	120.00
N2—C7—C8	131.64 (14)	C10—C11—H11	120.00
N2—C7—C20	105.12 (12)	C12—C11—H11	120.00
C8—C7—C20	123.21 (13)	C11—C12—H12	119.00
C7—C8—C9	124.93 (15)	C13—C12—H12	119.00
C7—C8—C13	115.67 (14)	C14—C15—H15	119.00
C9—C8—C13	119.38 (15)	C16—C15—H15	119.00
C8—C9—C10	121.32 (17)	C15—C16—H16	119.00
C9—C10—C11	119.83 (18)	C17—C16—H16	119.00
C10—C11—C12	120.1 (2)	C16—C17—H17	120.00
C11—C12—C13	122.54 (18)	C18—C17—H17	120.00
C8—C13—C12	116.76 (16)	C17—C18—H18	120.00
C8—C13—C14	121.27 (15)	C19—C18—H18	120.00
C12—C13—C14	121.97 (16)	C22—C23—H23	119.00
C13—C14—C15	122.53 (17)	C24—C23—H23	119.00
C13—C14—C19	120.65 (15)	C23—C24—H24	121.00
C15—C14—C19	116.82 (17)	C25—C24—H24	121.00
C14—C15—C16	121.47 (19)	C25—C26—H26	121.00
C15—C16—C17	121.3 (2)	C27—C26—H26	121.00
C16—C17—C18	119.4 (2)	C22—C27—H27	119.00
C17—C18—C19	120.32 (18)	C26—C27—H27	119.00
C14—C19—C18	120.78 (16)	C5—C28—H28A	109.00
C14—C19—C20	117.35 (15)	C5—C28—H28B	110.00
C18—C19—C20	121.87 (15)	C5—C28—H28C	109.00
N1—C20—C7	111.40 (13)	H28A—C28—H28B	109.00
N1—C20—C19	126.79 (14)	H28A—C28—H28C	109.00
C7—C20—C19	121.81 (14)	H28B—C28—H28C	109.00
N1—C21—N2	112.01 (14)	C1—C29—H29A	109.00
N1—C21—C22	123.78 (14)	C1—C29—H29B	109.00
N2—C21—C22	124.20 (14)	C1—C29—H29C	109.00
C21—C22—C23	118.68 (14)	H29A—C29—H29B	109.00
C21—C22—C27	123.46 (15)	H29A—C29—H29C	109.00
C23—C22—C27	117.85 (16)	H29B—C29—H29C	109.00
C22—C23—C24	121.09 (16)

C20—N1—C21—C22	−178.64 (14)	C7—C8—C13—C14	−1.7 (2)
C20—N1—C21—N2	0.33 (17)	C9—C8—C13—C12	−2.2 (2)
C21—N1—C20—C7	0.17 (17)	C8—C9—C10—C11	0.3 (3)
C21—N1—C20—C19	179.41 (15)	C9—C10—C11—C12	−1.4 (3)
C3—N2—C21—C22	3.7 (2)	C10—C11—C12—C13	0.6 (4)
C7—N2—C21—C22	178.27 (14)	C11—C12—C13—C14	−178.1 (2)
C3—N2—C7—C20	175.21 (13)	C11—C12—C13—C8	1.2 (3)
C21—N2—C7—C20	0.74 (16)	C8—C13—C14—C15	−179.38 (18)
C7—N2—C3—C4	−99.85 (18)	C12—C13—C14—C15	−0.2 (3)
C21—N2—C3—C4	73.6 (2)	C12—C13—C14—C19	179.18 (18)
C21—N2—C7—C8	−176.95 (16)	C8—C13—C14—C19	0.0 (3)
C21—N2—C3—C2	−106.97 (18)	C13—C14—C15—C16	178.9 (2)
C7—N2—C21—N1	−0.70 (17)	C19—C14—C15—C16	−0.5 (3)
C7—N2—C3—C2	79.61 (19)	C13—C14—C19—C18	−179.21 (16)
C3—N2—C21—N1	−175.24 (13)	C13—C14—C19—C20	0.8 (2)
C3—N2—C7—C8	−2.5 (3)	C15—C14—C19—C18	0.2 (3)
C2—C1—C6—C5	−0.5 (3)	C15—C14—C19—C20	−179.75 (17)
C29—C1—C6—C5	178.91 (16)	C14—C15—C16—C17	0.5 (4)
C6—C1—C2—C3	0.1 (2)	C15—C16—C17—C18	−0.3 (4)
C29—C1—C2—C3	−179.29 (15)	C16—C17—C18—C19	0.0 (3)
C1—C2—C3—N2	−178.84 (14)	C17—C18—C19—C20	179.97 (18)
C1—C2—C3—C4	0.6 (2)	C17—C18—C19—C14	0.0 (3)
N2—C3—C4—C5	178.51 (14)	C14—C19—C20—N1	−179.08 (15)
C2—C3—C4—C5	−0.9 (2)	C18—C19—C20—N1	1.0 (3)
C3—C4—C5—C28	−178.70 (16)	C18—C19—C20—C7	−179.86 (15)
C3—C4—C5—C6	0.6 (2)	C14—C19—C20—C7	0.1 (2)
C4—C5—C6—C1	0.1 (3)	N1—C21—C22—C23	34.4 (2)
C28—C5—C6—C1	179.37 (17)	N1—C21—C22—C27	−143.96 (17)
N2—C7—C8—C13	179.98 (16)	N2—C21—C22—C23	−144.46 (16)
C20—C7—C8—C9	−176.01 (16)	N2—C21—C22—C27	37.2 (2)
C20—C7—C8—C13	2.7 (2)	C21—C22—C23—C24	−179.86 (15)
N2—C7—C20—N1	−0.58 (17)	C27—C22—C23—C24	−1.4 (2)
N2—C7—C20—C19	−179.87 (14)	C21—C22—C27—C26	179.74 (18)
C8—C7—C20—N1	177.36 (14)	C23—C22—C27—C26	1.4 (3)
N2—C7—C8—C9	1.3 (3)	C22—C23—C24—C25	0.3 (3)
C8—C7—C20—C19	−1.9 (2)	C23—C24—C25—F1	−178.82 (16)
C9—C8—C13—C14	177.08 (16)	C23—C24—C25—C26	1.0 (3)
C7—C8—C9—C10	−179.91 (17)	F1—C25—C26—C27	178.79 (18)
C13—C8—C9—C10	1.5 (3)	C24—C25—C26—C27	−1.0 (3)
C7—C8—C13—C12	179.11 (17)	C25—C26—C27—C22	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C7/C8/C13/C14/C19/C20 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1	0.9300	2.9700	3.8433	156.00
C6—H6···Cg2ⁱ	0.9300	2.9700	3.6994	155.00

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₁FN₂
M_r	416.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	8.5680 (2), 10.6070 (3), 23.6900 (6)
β (°)	93.899 (1)
V (Å³)	2147.98 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.952, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	19934, 3777, 2957
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.02
No. of reflections	3777
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.15

Computer programs: APEX2 (Bruker, 2008), APEX2 and SAINT (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C7/C8/C13/C14/C19/C20 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1	0.9300	2.9700	3.8433	156.00
C6—H6···Cg2ⁱ	0.9300	2.9700	3.6994	155.00

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 69| Part 3| March 2013| Page o367

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