2-(4-Fluoro-phen-yl)-1-(4-methyl-phen-yl)-1H-phenanthro[9,10-d]imidazole.

The phenanthrene tricyclic ring system in the title mol-ecule, C(28)H(19)FN(2), is slightly skewed with a dihedral angle of 7.50 (6)° between the outer benzene rings. The p-tolyl and fluoro-benzene rings are twisted from the attached imidazole ring by 70.40 (7) and 28.33 (7)°, respectively. In the crystal, C-H⋯F hydrogen bonds link the mol-ecules into zigzag chains in [001], and weak C-H⋯π inter-actions further consolidate the crystal packing.

Related literature

For related structures, see: Yuan et al. (2011 ▶); Rosepriya et al. (2011 ▶).

Experimental

Crystal data

C28H19FN2

M = 402.45

Monoclinic,

a = 10.1809 (2) Å

b = 10.7654 (2) Å

c = 18.4871 (3) Å

β = 96.115 (1)°

V = 2014.68 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 123 K

0.45 × 0.35 × 0.25 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.753, T max = 0.850

8155 measured reflections

4054 independent reflections

3619 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.03

4054 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2011 (Burla et al., 2012 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037592/cv5332sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037592/cv5332Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037592/cv5332Isup3.cdx

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

C28H19FN2	F(000) = 840
Mr = 402.45	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Melting point: 494 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 10.1809 (2) Å	Cell parameters from 4975 reflections
b = 10.7654 (2) Å	θ = 4.1–75.3°
c = 18.4871 (3) Å	µ = 0.67 mm−1
β = 96.115 (1)°	T = 123 K
V = 2014.68 (6) Å3	Block, colourless
Z = 4	0.45 × 0.35 × 0.25 mm

Agilent Xcalibur Ruby Gemini diffractometer	4054 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 75.5°, θmin = 4.4°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→13
Tmin = 0.753, Tmax = 0.850	l = −22→13
8155 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.6604P] where P = (Fo2 + 2Fc2)/3
4054 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 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 > 2σ(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
F4	0.18868 (10)	0.04100 (8)	−0.00640 (5)	0.0413 (3)
N1	0.22790 (10)	0.50374 (10)	0.22352 (5)	0.0213 (3)
N3	0.32302 (10)	0.57512 (10)	0.12764 (6)	0.0230 (3)
C2	0.26496 (12)	0.47886 (12)	0.15502 (7)	0.0222 (3)
C4	0.32401 (12)	0.66606 (12)	0.18005 (6)	0.0213 (3)
C5	0.26743 (12)	0.62474 (11)	0.24026 (6)	0.0207 (3)
C6	0.26588 (12)	0.69804 (12)	0.30544 (6)	0.0212 (3)
C7	0.22497 (13)	0.65420 (12)	0.37131 (7)	0.0253 (3)
C8	0.23298 (14)	0.72837 (13)	0.43239 (7)	0.0282 (4)
C9	0.28381 (14)	0.84865 (13)	0.43030 (7)	0.0299 (4)
C10	0.32612 (13)	0.89271 (13)	0.36685 (7)	0.0273 (4)
C11	0.31801 (12)	0.82110 (12)	0.30268 (7)	0.0223 (3)
C12	0.36582 (12)	0.86934 (12)	0.23605 (7)	0.0227 (3)
C13	0.40522 (13)	0.99443 (13)	0.22925 (7)	0.0266 (4)
C14	0.44945 (13)	1.03779 (13)	0.16616 (8)	0.0296 (4)
C15	0.45837 (13)	0.95801 (14)	0.10720 (7)	0.0298 (4)
C16	0.41987 (13)	0.83594 (13)	0.11144 (7)	0.0260 (4)
C17	0.37198 (12)	0.79098 (12)	0.17515 (7)	0.0221 (3)
C18	0.17293 (12)	0.41523 (12)	0.27015 (6)	0.0214 (3)
C19	0.04292 (13)	0.42709 (13)	0.28571 (7)	0.0258 (4)
C20	−0.00771 (13)	0.34031 (13)	0.33123 (7)	0.0287 (4)
C21	0.06862 (14)	0.24164 (13)	0.36048 (7)	0.0286 (4)
C22	0.19820 (14)	0.23184 (13)	0.34311 (7)	0.0286 (4)
C23	0.25117 (13)	0.31826 (12)	0.29870 (7)	0.0247 (3)
C24	0.24119 (12)	0.36103 (12)	0.11511 (7)	0.0231 (3)
C25	0.13499 (13)	0.28159 (13)	0.12329 (7)	0.0276 (4)
C26	0.11766 (14)	0.17314 (13)	0.08261 (7)	0.0299 (4)
C27	0.20587 (15)	0.14662 (13)	0.03352 (7)	0.0291 (4)
C28	0.31057 (14)	0.22303 (13)	0.02274 (7)	0.0297 (4)
C29	0.32810 (13)	0.33064 (13)	0.06400 (7)	0.0263 (4)
C30	0.01479 (16)	0.14695 (15)	0.41001 (8)	0.0383 (4)
H7	0.19202	0.57389	0.37360	0.0303*
H8	0.20442	0.69819	0.47518	0.0339*
H9	0.28904	0.89866	0.47152	0.0358*
H10	0.36123	0.97241	0.36629	0.0327*
H13	0.40115	1.04845	0.26821	0.0319*
H14	0.47357	1.12073	0.16270	0.0355*
H15	0.49032	0.98744	0.06514	0.0357*
H16	0.42550	0.78302	0.07213	0.0312*
H19	−0.00949	0.49204	0.26601	0.0310*
H20	−0.09428	0.34849	0.34230	0.0344*
H22	0.25028	0.16587	0.36171	0.0343*
H23	0.33821	0.31109	0.28827	0.0296*
H25	0.07540	0.30157	0.15628	0.0331*
H26	0.04784	0.11968	0.08852	0.0358*
H28	0.36809	0.20301	−0.01134	0.0356*
H29	0.39843	0.38321	0.05761	0.0315*
H30A	−0.07357	0.16950	0.41836	0.0575*
H30B	0.06969	0.14470	0.45555	0.0575*
H30C	0.01404	0.06650	0.38757	0.0575*

	U11	U22	U33	U12	U13	U23
F4	0.0566 (6)	0.0297 (4)	0.0377 (5)	0.0015 (4)	0.0052 (4)	−0.0148 (4)
N1	0.0245 (5)	0.0200 (5)	0.0198 (5)	−0.0001 (4)	0.0042 (4)	−0.0014 (4)
N3	0.0239 (5)	0.0235 (5)	0.0219 (5)	0.0008 (4)	0.0038 (4)	−0.0008 (4)
C2	0.0226 (6)	0.0242 (6)	0.0201 (6)	0.0027 (5)	0.0037 (4)	−0.0003 (5)
C4	0.0213 (5)	0.0230 (6)	0.0196 (5)	0.0018 (5)	0.0023 (4)	0.0005 (5)
C5	0.0209 (5)	0.0198 (6)	0.0213 (6)	0.0009 (5)	0.0020 (4)	0.0005 (5)
C6	0.0216 (5)	0.0219 (6)	0.0202 (6)	0.0023 (5)	0.0021 (4)	−0.0002 (5)
C7	0.0284 (6)	0.0237 (6)	0.0241 (6)	−0.0009 (5)	0.0049 (5)	0.0008 (5)
C8	0.0342 (7)	0.0306 (7)	0.0206 (6)	0.0003 (5)	0.0063 (5)	−0.0007 (5)
C9	0.0395 (7)	0.0275 (7)	0.0225 (6)	0.0023 (6)	0.0030 (5)	−0.0052 (5)
C10	0.0330 (7)	0.0211 (6)	0.0276 (6)	−0.0001 (5)	0.0024 (5)	−0.0022 (5)
C11	0.0226 (6)	0.0213 (6)	0.0227 (6)	0.0026 (5)	0.0013 (4)	0.0002 (5)
C12	0.0207 (5)	0.0228 (6)	0.0241 (6)	0.0002 (5)	0.0005 (4)	0.0023 (5)
C13	0.0274 (6)	0.0245 (7)	0.0275 (6)	−0.0026 (5)	0.0009 (5)	−0.0001 (5)
C14	0.0289 (6)	0.0247 (7)	0.0344 (7)	−0.0052 (5)	−0.0002 (5)	0.0066 (6)
C15	0.0282 (7)	0.0346 (7)	0.0266 (6)	−0.0038 (5)	0.0033 (5)	0.0086 (6)
C16	0.0243 (6)	0.0305 (7)	0.0230 (6)	−0.0003 (5)	0.0021 (5)	0.0028 (5)
C17	0.0189 (5)	0.0245 (6)	0.0226 (6)	0.0012 (5)	0.0011 (4)	0.0025 (5)
C18	0.0258 (6)	0.0204 (6)	0.0184 (5)	−0.0032 (5)	0.0039 (4)	−0.0021 (5)
C19	0.0253 (6)	0.0271 (7)	0.0251 (6)	0.0011 (5)	0.0027 (5)	−0.0011 (5)
C20	0.0241 (6)	0.0356 (7)	0.0270 (6)	−0.0064 (5)	0.0054 (5)	−0.0034 (6)
C21	0.0352 (7)	0.0285 (7)	0.0218 (6)	−0.0104 (5)	0.0021 (5)	−0.0013 (5)
C22	0.0350 (7)	0.0238 (7)	0.0267 (6)	0.0010 (5)	0.0017 (5)	0.0019 (5)
C23	0.0255 (6)	0.0251 (6)	0.0239 (6)	0.0002 (5)	0.0045 (5)	−0.0021 (5)
C24	0.0264 (6)	0.0230 (6)	0.0198 (6)	0.0028 (5)	0.0017 (4)	−0.0002 (5)
C25	0.0295 (6)	0.0286 (7)	0.0252 (6)	−0.0005 (5)	0.0057 (5)	−0.0048 (5)
C26	0.0338 (7)	0.0268 (7)	0.0289 (7)	−0.0032 (5)	0.0029 (5)	−0.0023 (5)
C27	0.0399 (7)	0.0221 (6)	0.0242 (6)	0.0051 (5)	−0.0013 (5)	−0.0058 (5)
C28	0.0345 (7)	0.0316 (7)	0.0237 (6)	0.0083 (6)	0.0066 (5)	−0.0030 (5)
C29	0.0274 (6)	0.0275 (7)	0.0241 (6)	0.0027 (5)	0.0039 (5)	0.0000 (5)
C30	0.0428 (8)	0.0407 (8)	0.0313 (7)	−0.0165 (7)	0.0031 (6)	0.0049 (6)

F4—C27	1.3567 (16)	C21—C30	1.512 (2)
N1—C2	1.3855 (16)	C22—C23	1.3874 (19)
N1—C5	1.3885 (16)	C24—C25	1.3993 (18)
N1—C18	1.4377 (16)	C24—C29	1.4003 (18)
N3—C2	1.3203 (17)	C25—C26	1.3898 (19)
N3—C4	1.3767 (16)	C26—C27	1.373 (2)
C2—C24	1.4744 (18)	C27—C28	1.378 (2)
C4—C5	1.3803 (16)	C28—C29	1.3881 (19)
C4—C17	1.4369 (18)	C7—H7	0.9300
C5—C6	1.4419 (16)	C8—H8	0.9300
C6—C7	1.4097 (17)	C9—H9	0.9300
C6—C11	1.4301 (18)	C10—H10	0.9300
C7—C8	1.3783 (18)	C13—H13	0.9300
C8—C9	1.397 (2)	C14—H14	0.9300
C9—C10	1.3763 (19)	C15—H15	0.9300
C10—C11	1.4098 (18)	C16—H16	0.9300
C11—C12	1.4669 (18)	C19—H19	0.9300
C12—C13	1.4145 (19)	C20—H20	0.9300
C12—C17	1.4136 (18)	C22—H22	0.9300
C13—C14	1.3758 (19)	C23—H23	0.9300
C14—C15	1.398 (2)	C25—H25	0.9300
C15—C16	1.376 (2)	C26—H26	0.9300
C16—C17	1.4077 (18)	C28—H28	0.9300
C18—C19	1.3900 (18)	C29—H29	0.9300
C18—C23	1.3832 (18)	C30—H30A	0.9600
C19—C20	1.3925 (19)	C30—H30B	0.9600
C20—C21	1.391 (2)	C30—H30C	0.9600
C21—C22	1.395 (2)
C2—N1—C5	106.52 (10)	C24—C25—C26	120.66 (12)
C2—N1—C18	125.54 (10)	C25—C26—C27	118.56 (13)
C5—N1—C18	127.60 (10)	F4—C27—C26	118.57 (13)
C2—N3—C4	104.97 (11)	F4—C27—C28	118.60 (12)
N1—C2—N3	112.04 (11)	C26—C27—C28	122.83 (13)
N1—C2—C24	125.28 (11)	C27—C28—C29	118.36 (13)
N3—C2—C24	122.66 (11)	C24—C29—C28	120.82 (12)
N3—C4—C5	111.47 (11)	C6—C7—H7	119.00
N3—C4—C17	126.74 (11)	C8—C7—H7	119.00
C5—C4—C17	121.76 (11)	C7—C8—H8	120.00
N1—C5—C4	104.98 (10)	C9—C8—H8	120.00
N1—C5—C6	132.14 (11)	C8—C9—H9	120.00
C4—C5—C6	122.70 (11)	C10—C9—H9	120.00
C5—C6—C7	124.70 (12)	C9—C10—H10	119.00
C5—C6—C11	116.11 (10)	C11—C10—H10	119.00
C7—C6—C11	119.07 (11)	C12—C13—H13	119.00
C6—C7—C8	121.11 (12)	C14—C13—H13	119.00
C7—C8—C9	120.28 (12)	C13—C14—H14	120.00
C8—C9—C10	119.58 (12)	C15—C14—H14	120.00
C9—C10—C11	122.22 (13)	C14—C15—H15	120.00
C6—C11—C10	117.73 (11)	C16—C15—H15	120.00
C6—C11—C12	121.03 (11)	C15—C16—H16	120.00
C10—C11—C12	121.21 (12)	C17—C16—H16	120.00
C11—C12—C13	122.30 (12)	C18—C19—H19	120.00
C11—C12—C17	120.29 (11)	C20—C19—H19	120.00
C13—C12—C17	117.41 (12)	C19—C20—H20	119.00
C12—C13—C14	121.32 (12)	C21—C20—H20	119.00
C13—C14—C15	120.45 (13)	C21—C22—H22	119.00
C14—C15—C16	119.98 (12)	C23—C22—H22	119.00
C15—C16—C17	120.15 (12)	C18—C23—H23	120.00
C4—C17—C12	117.65 (11)	C22—C23—H23	120.00
C4—C17—C16	121.66 (12)	C24—C25—H25	120.00
C12—C17—C16	120.66 (12)	C26—C25—H25	120.00
N1—C18—C19	120.22 (11)	C25—C26—H26	121.00
N1—C18—C23	118.94 (11)	C27—C26—H26	121.00
C19—C18—C23	120.85 (12)	C27—C28—H28	121.00
C18—C19—C20	119.04 (12)	C29—C28—H28	121.00
C19—C20—C21	121.32 (12)	C24—C29—H29	120.00
C20—C21—C22	118.12 (12)	C28—C29—H29	120.00
C20—C21—C30	121.79 (13)	C21—C30—H30A	109.00
C22—C21—C30	120.09 (13)	C21—C30—H30B	109.00
C21—C22—C23	121.49 (13)	C21—C30—H30C	109.00
C18—C23—C22	119.18 (12)	H30A—C30—H30B	109.00
C2—C24—C25	124.00 (11)	H30A—C30—H30C	109.00
C2—C24—C29	117.18 (11)	H30B—C30—H30C	109.00
C25—C24—C29	118.76 (12)
C5—N1—C2—N3	−0.67 (14)	C7—C8—C9—C10	−0.1 (2)
C5—N1—C2—C24	−179.32 (12)	C8—C9—C10—C11	1.1 (2)
C18—N1—C2—N3	−174.41 (11)	C9—C10—C11—C6	−1.14 (19)
C18—N1—C2—C24	6.95 (19)	C9—C10—C11—C12	−178.96 (13)
C2—N1—C5—C4	1.00 (13)	C6—C11—C12—C13	173.38 (12)
C2—N1—C5—C6	−174.12 (13)	C6—C11—C12—C17	−5.61 (18)
C18—N1—C5—C4	174.57 (11)	C10—C11—C12—C13	−8.88 (19)
C18—N1—C5—C6	−0.6 (2)	C10—C11—C12—C17	172.14 (12)
C2—N1—C18—C19	−112.80 (14)	C11—C12—C13—C14	−179.83 (12)
C2—N1—C18—C23	66.83 (16)	C17—C12—C13—C14	−0.82 (19)
C5—N1—C18—C19	74.79 (16)	C11—C12—C17—C4	3.00 (18)
C5—N1—C18—C23	−105.58 (15)	C11—C12—C17—C16	−178.90 (12)
C4—N3—C2—N1	0.03 (13)	C13—C12—C17—C4	−176.03 (11)
C4—N3—C2—C24	178.71 (11)	C13—C12—C17—C16	2.07 (18)
C2—N3—C4—C5	0.65 (14)	C12—C13—C14—C15	−1.0 (2)
C2—N3—C4—C17	−177.29 (12)	C13—C14—C15—C16	1.5 (2)
N1—C2—C24—C25	28.9 (2)	C14—C15—C16—C17	−0.3 (2)
N1—C2—C24—C29	−153.74 (12)	C15—C16—C17—C4	176.46 (12)
N3—C2—C24—C25	−149.60 (13)	C15—C16—C17—C12	−1.56 (19)
N3—C2—C24—C29	27.75 (18)	N1—C18—C19—C20	−179.79 (11)
N3—C4—C5—N1	−1.05 (14)	C23—C18—C19—C20	0.59 (19)
N3—C4—C5—C6	174.66 (11)	N1—C18—C23—C22	−179.33 (11)
C17—C4—C5—N1	177.01 (11)	C19—C18—C23—C22	0.30 (19)
C17—C4—C5—C6	−7.28 (19)	C18—C19—C20—C21	−0.8 (2)
N3—C4—C17—C12	−178.97 (12)	C19—C20—C21—C22	0.2 (2)
N3—C4—C17—C16	2.9 (2)	C19—C20—C21—C30	179.94 (13)
C5—C4—C17—C12	3.28 (18)	C20—C21—C22—C23	0.8 (2)
C5—C4—C17—C16	−174.80 (12)	C30—C21—C22—C23	−179.02 (13)
N1—C5—C6—C7	3.0 (2)	C21—C22—C23—C18	−1.0 (2)
N1—C5—C6—C11	178.89 (12)	C2—C24—C25—C26	178.69 (12)
C4—C5—C6—C7	−171.39 (12)	C29—C24—C25—C26	1.39 (19)
C4—C5—C6—C11	4.49 (18)	C2—C24—C29—C28	−178.28 (12)
C5—C6—C7—C8	176.56 (13)	C25—C24—C29—C28	−0.8 (2)
C11—C6—C7—C8	0.80 (19)	C24—C25—C26—C27	−0.9 (2)
C5—C6—C11—C10	−175.94 (11)	C25—C26—C27—F4	−179.75 (12)
C5—C6—C11—C12	1.88 (17)	C25—C26—C27—C28	−0.2 (2)
C7—C6—C11—C10	0.18 (18)	F4—C27—C28—C29	−179.67 (12)
C7—C6—C11—C12	178.00 (12)	C26—C27—C28—C29	0.8 (2)
C6—C7—C8—C9	−0.9 (2)	C27—C28—C29—C24	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F4i	0.93	2.54	3.1371 (16)	122
C14—H14···Cg2ii	0.93	2.95	3.5613 (15)	125
C20—H20···Cg2iii	0.93	2.84	3.4540 (14)	125
C23—H23···Cg3iv	0.93	2.81	3.5709 (14)	140
C30—H30A···Cg1iii	0.96	2.91	3.4294 (17)	115
C30—H30B···Cg4i	0.96	2.77	3.6659 (16)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C2/N3/C4/C5, C4–C6/C11/C12/C17, C12–C17 and C24–C29 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F4i	0.93	2.54	3.1371 (16)	122
C14—H14⋯Cg2ii	0.93	2.95	3.5613 (15)	125
C20—H20⋯Cg2iii	0.93	2.84	3.4540 (14)	125
C23—H23⋯Cg3iv	0.93	2.81	3.5709 (14)	140
C30—H30A⋯Cg1iii	0.96	2.91	3.4294 (17)	115
C30—H30B⋯Cg4i	0.96	2.77	3.6659 (16)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .