1-(3,5-Dimethyl-phen-yl)-2-(4-fluoro-phen-yl)-1H-phenanthro[9,10-d]imidazole.

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 dimethyl-phenyl and fluoro-phenyl rings, respectively. The crystal packing features weak C-H⋯π inter-actions involving the dimethyl-phenyl 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 = 416.48

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.02

3777 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.15 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813003486/rk2393sup1.cif

Click here for additional data file.

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

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

C29H21FN2	F(000) = 872
Mr = 416.48	Dx = 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

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

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(Fo2) + (0.047P)2 + 0.6584P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3777 reflections	Δρmax = 0.24 e Å−3
292 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .