2-(4-Fluoro-phen-yl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline monohydrate.

In the title compound, C(25)H(15)FN(4)·H(2)O, the fused ring system is essentially planar [maximum deviation of 0.0822 (14) Å]. The imidazole ring makes dihedral angles of 76.83 (7) and 32.22 (7)° with the phenyl group attached to nitro-gen and the fluoro-benzene group to carbon, respectively. The dihedral angle between the two phenyl rings is 72.13 (7)°. Inter-molecular O-H⋯N, O-H⋯F, C-H⋯F, C-H⋯O and C-H⋯N hydrogen bonds are found in the crystal structure.

Related literature

For a related structure, see: Rosepriya et al. (2011 ▶). For technological and biological applications of related compounds, see: Liu et al. (2005 ▶); Bian et al. (2002 ▶).

Experimental

Crystal data

C25H15FN4·H2O

M = 408.43

Triclinic,

a = 9.0103 (10) Å

b = 10.0946 (9) Å

c = 11.3994 (9) Å

α = 86.987 (7)°

β = 75.950 (8)°

γ = 82.396 (8)°

V = 996.75 (17) Å3

Z = 2

Cu Kα radiation

μ = 0.75 mm−1

T = 170 K

0.34 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.784, T max = 0.864

6315 measured reflections

3765 independent reflections

3382 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.04

3765 reflections

288 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026328/hg5061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026328/hg5061Isup2.hkl

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

C25H15FN4·H2O	Z = 2
Mr = 408.43	F(000) = 424
Triclinic, P1	Dx = 1.361 Mg m−3
Hall symbol: -P 1	Melting point: 567 K
a = 9.0103 (10) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.0946 (9) Å	Cell parameters from 4456 reflections
c = 11.3994 (9) Å	θ = 4.0–71.6°
α = 86.987 (7)°	µ = 0.75 mm−1
β = 75.950 (8)°	T = 170 K
γ = 82.396 (8)°	Block, pale-yellow
V = 996.75 (17) Å3	0.34 × 0.25 × 0.20 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3765 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3382 reflections with I > 2σ(I)
graphite	Rint = 0.013
Detector resolution: 16.1500 pixels mm-1	θmax = 71.7°, θmin = 4.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→11
Tmin = 0.784, Tmax = 0.864	l = −13→9
6315 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1908P] where P = (Fo2 + 2Fc2)/3
3765 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 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	0.97668 (13)	−0.28116 (12)	0.54415 (10)	0.0786 (4)
N1	0.92907 (12)	0.16988 (11)	0.12069 (9)	0.0359 (3)
N3	1.18158 (12)	0.09894 (11)	0.08946 (10)	0.0391 (3)
N10	1.01571 (15)	0.48776 (13)	−0.23133 (12)	0.0521 (4)
N13	1.31915 (15)	0.39690 (13)	−0.26380 (11)	0.0501 (4)
C2	1.04372 (15)	0.08612 (13)	0.15819 (11)	0.0369 (4)
C4	1.15633 (15)	0.19490 (13)	0.00436 (11)	0.0368 (4)
C5	1.00239 (15)	0.24120 (13)	0.02073 (11)	0.0358 (4)
C6	0.94466 (15)	0.34434 (13)	−0.05427 (12)	0.0372 (4)
C7	0.79054 (17)	0.40253 (15)	−0.03881 (14)	0.0457 (4)
C8	0.75310 (18)	0.49897 (16)	−0.11884 (15)	0.0532 (5)
C9	0.8689 (2)	0.53716 (17)	−0.21396 (16)	0.0584 (5)
C11	1.05532 (16)	0.39312 (13)	−0.15231 (12)	0.0394 (4)
C12	1.21950 (16)	0.34406 (14)	−0.17030 (12)	0.0400 (4)
C14	1.46849 (18)	0.35781 (17)	−0.27695 (15)	0.0551 (5)
C15	1.52874 (18)	0.26431 (17)	−0.20121 (15)	0.0529 (5)
C16	1.42936 (16)	0.20624 (16)	−0.10893 (13)	0.0456 (4)
C17	1.27071 (15)	0.24631 (14)	−0.09146 (12)	0.0380 (4)
C18	0.76897 (14)	0.19088 (13)	0.18319 (11)	0.0353 (3)
C19	0.66066 (16)	0.13798 (15)	0.13745 (13)	0.0433 (4)
C20	0.50721 (17)	0.15814 (17)	0.19911 (14)	0.0515 (5)
C21	0.46428 (17)	0.22966 (18)	0.30488 (15)	0.0545 (5)
C22	0.57309 (18)	0.28226 (17)	0.34889 (14)	0.0540 (5)
C23	0.72683 (17)	0.26361 (14)	0.28769 (13)	0.0441 (4)
C24	1.01826 (15)	−0.00849 (13)	0.26178 (12)	0.0383 (4)
C25	0.88803 (18)	−0.07485 (15)	0.29655 (13)	0.0458 (4)
C26	0.87439 (19)	−0.16753 (16)	0.39112 (14)	0.0518 (5)
C27	0.99130 (19)	−0.19174 (16)	0.45003 (14)	0.0525 (5)
C28	1.12160 (18)	−0.12905 (18)	0.41907 (15)	0.0563 (5)
C29	1.13416 (16)	−0.03709 (16)	0.32457 (14)	0.0483 (5)
O1W	0.26297 (19)	0.49467 (15)	0.50499 (13)	0.0729 (5)
H7	0.71305	0.37486	0.02691	0.0549*
H8	0.64960	0.53925	−0.10958	0.0639*
H9	0.84085	0.60287	−0.27007	0.0701*
H14	1.53858	0.39588	−0.34194	0.0662*
H15	1.63700	0.24125	−0.21342	0.0636*
H16	1.46717	0.13990	−0.05757	0.0547*
H19	0.69131	0.08871	0.06496	0.0519*
H20	0.43144	0.12293	0.16887	0.0618*
H21	0.35903	0.24259	0.34746	0.0654*
H22	0.54251	0.33145	0.42142	0.0647*
H23	0.80214	0.30036	0.31725	0.0529*
H25	0.80786	−0.05634	0.25498	0.0549*
H26	0.78593	−0.21339	0.41473	0.0621*
H28	1.20088	−0.14836	0.46145	0.0675*
H29	1.22349	0.00773	0.30171	0.0580*
H1W	0.260 (3)	0.470 (3)	0.588 (3)	0.115 (9)*
H2W	0.161 (4)	0.521 (3)	0.507 (3)	0.115 (10)*

	U11	U22	U33	U12	U13	U23
F4	0.0789 (7)	0.0849 (8)	0.0670 (7)	−0.0159 (6)	−0.0147 (5)	0.0469 (6)
N1	0.0323 (5)	0.0407 (6)	0.0329 (5)	−0.0076 (4)	−0.0042 (4)	0.0066 (4)
N3	0.0338 (5)	0.0466 (6)	0.0347 (6)	−0.0061 (5)	−0.0048 (4)	0.0066 (5)
N10	0.0500 (7)	0.0548 (7)	0.0476 (7)	−0.0085 (6)	−0.0071 (6)	0.0181 (6)
N13	0.0477 (7)	0.0549 (7)	0.0423 (7)	−0.0139 (6)	0.0011 (5)	0.0114 (5)
C2	0.0354 (7)	0.0406 (7)	0.0339 (6)	−0.0068 (5)	−0.0064 (5)	0.0039 (5)
C4	0.0339 (6)	0.0431 (7)	0.0327 (6)	−0.0092 (5)	−0.0049 (5)	0.0032 (5)
C5	0.0351 (7)	0.0405 (7)	0.0312 (6)	−0.0105 (5)	−0.0044 (5)	0.0036 (5)
C6	0.0367 (7)	0.0397 (7)	0.0351 (7)	−0.0090 (5)	−0.0071 (5)	0.0033 (5)
C7	0.0391 (7)	0.0484 (8)	0.0470 (8)	−0.0078 (6)	−0.0062 (6)	0.0098 (6)
C8	0.0433 (8)	0.0537 (9)	0.0601 (10)	−0.0023 (7)	−0.0123 (7)	0.0129 (7)
C9	0.0563 (9)	0.0576 (9)	0.0580 (10)	−0.0043 (7)	−0.0143 (7)	0.0240 (8)
C11	0.0428 (7)	0.0399 (7)	0.0351 (7)	−0.0103 (5)	−0.0071 (5)	0.0056 (5)
C12	0.0416 (7)	0.0430 (7)	0.0338 (6)	−0.0125 (6)	−0.0028 (5)	0.0029 (5)
C14	0.0451 (8)	0.0644 (10)	0.0483 (8)	−0.0177 (7)	0.0070 (7)	0.0100 (7)
C15	0.0373 (8)	0.0648 (10)	0.0515 (9)	−0.0111 (7)	0.0017 (6)	0.0001 (7)
C16	0.0380 (7)	0.0548 (8)	0.0419 (7)	−0.0089 (6)	−0.0046 (6)	0.0028 (6)
C17	0.0359 (7)	0.0444 (7)	0.0331 (6)	−0.0109 (5)	−0.0041 (5)	0.0004 (5)
C18	0.0319 (6)	0.0381 (6)	0.0333 (6)	−0.0071 (5)	−0.0036 (5)	0.0088 (5)
C19	0.0395 (7)	0.0519 (8)	0.0383 (7)	−0.0120 (6)	−0.0064 (5)	0.0036 (6)
C20	0.0367 (7)	0.0685 (10)	0.0508 (9)	−0.0165 (7)	−0.0106 (6)	0.0108 (7)
C21	0.0335 (7)	0.0713 (10)	0.0498 (9)	−0.0014 (7)	0.0024 (6)	0.0092 (7)
C22	0.0498 (9)	0.0608 (9)	0.0434 (8)	−0.0001 (7)	0.0012 (6)	−0.0046 (7)
C23	0.0432 (7)	0.0471 (7)	0.0413 (7)	−0.0075 (6)	−0.0076 (6)	−0.0007 (6)
C24	0.0384 (7)	0.0398 (7)	0.0328 (6)	−0.0035 (5)	−0.0029 (5)	0.0039 (5)
C25	0.0512 (8)	0.0472 (8)	0.0424 (7)	−0.0147 (6)	−0.0150 (6)	0.0086 (6)
C26	0.0563 (9)	0.0503 (8)	0.0488 (8)	−0.0194 (7)	−0.0087 (7)	0.0118 (7)
C27	0.0566 (9)	0.0513 (8)	0.0429 (8)	−0.0032 (7)	−0.0046 (7)	0.0181 (7)
C28	0.0437 (8)	0.0697 (10)	0.0507 (9)	−0.0003 (7)	−0.0105 (7)	0.0206 (8)
C29	0.0350 (7)	0.0579 (9)	0.0474 (8)	−0.0049 (6)	−0.0047 (6)	0.0143 (7)
O1W	0.0730 (9)	0.0857 (10)	0.0516 (8)	−0.0067 (7)	−0.0022 (6)	0.0075 (6)

F4—C27	1.358 (2)	C18—C19	1.387 (2)
O1W—H1W	0.96 (3)	C19—C20	1.384 (2)
O1W—H2W	0.92 (4)	C20—C21	1.384 (2)
N1—C18	1.4386 (17)	C21—C22	1.378 (2)
N1—C2	1.3821 (17)	C22—C23	1.384 (2)
N1—C5	1.3883 (16)	C24—C29	1.396 (2)
N3—C4	1.3716 (17)	C24—C25	1.392 (2)
N3—C2	1.3164 (18)	C25—C26	1.383 (2)
N10—C11	1.3516 (19)	C26—C27	1.371 (2)
N10—C9	1.322 (2)	C27—C28	1.369 (2)
N13—C12	1.3524 (19)	C28—C29	1.378 (2)
N13—C14	1.325 (2)	C7—H7	0.9500
C2—C24	1.4721 (18)	C8—H8	0.9500
C4—C5	1.374 (2)	C9—H9	0.9500
C4—C17	1.4353 (19)	C14—H14	0.9500
C5—C6	1.4369 (19)	C15—H15	0.9500
C6—C11	1.4201 (19)	C16—H16	0.9500
C6—C7	1.407 (2)	C19—H19	0.9500
C7—C8	1.365 (2)	C20—H20	0.9500
C8—C9	1.388 (2)	C21—H21	0.9500
C11—C12	1.465 (2)	C22—H22	0.9500
C12—C17	1.408 (2)	C23—H23	0.9500
C14—C15	1.392 (2)	C25—H25	0.9500
C15—C16	1.367 (2)	C26—H26	0.9500
C16—C17	1.401 (2)	C28—H28	0.9500
C18—C23	1.3787 (19)	C29—H29	0.9500
H1W—O1W—H2W	102 (3)	C18—C23—C22	118.99 (14)
C2—N1—C18	126.14 (10)	C2—C24—C25	123.33 (13)
C5—N1—C18	127.06 (11)	C2—C24—C29	117.98 (13)
C2—N1—C5	106.32 (11)	C25—C24—C29	118.63 (13)
C2—N3—C4	104.84 (11)	C24—C25—C26	120.54 (15)
C9—N10—C11	117.97 (14)	C25—C26—C27	118.54 (16)
C12—N13—C14	118.04 (13)	F4—C27—C26	118.50 (15)
N1—C2—N3	112.21 (11)	C26—C27—C28	123.04 (15)
N1—C2—C24	125.07 (12)	F4—C27—C28	118.46 (15)
N3—C2—C24	122.72 (12)	C27—C28—C29	117.95 (15)
N3—C4—C5	111.71 (11)	C24—C29—C28	121.30 (14)
N3—C4—C17	126.82 (12)	C8—C7—H7	120.00
C5—C4—C17	121.46 (12)	C6—C7—H7	120.00
N1—C5—C6	131.96 (13)	C9—C8—H8	121.00
C4—C5—C6	123.11 (12)	C7—C8—H8	121.00
N1—C5—C4	104.91 (11)	N10—C9—H9	118.00
C5—C6—C11	116.29 (12)	C8—C9—H9	118.00
C7—C6—C11	117.27 (12)	N13—C14—H14	118.00
C5—C6—C7	126.43 (13)	C15—C14—H14	118.00
C6—C7—C8	119.59 (14)	C16—C15—H15	121.00
C7—C8—C9	118.83 (16)	C14—C15—H15	121.00
N10—C9—C8	124.07 (16)	C15—C16—H16	121.00
N10—C11—C12	116.99 (12)	C17—C16—H16	121.00
C6—C11—C12	120.77 (12)	C20—C19—H19	121.00
N10—C11—C6	122.22 (13)	C18—C19—H19	121.00
N13—C12—C11	117.77 (12)	C19—C20—H20	120.00
C11—C12—C17	120.63 (12)	C21—C20—H20	120.00
N13—C12—C17	121.60 (13)	C22—C21—H21	120.00
N13—C14—C15	123.90 (15)	C20—C21—H21	120.00
C14—C15—C16	118.82 (15)	C21—C22—H22	120.00
C15—C16—C17	118.81 (14)	C23—C22—H22	120.00
C4—C17—C12	117.64 (13)	C22—C23—H23	121.00
C4—C17—C16	123.59 (13)	C18—C23—H23	121.00
C12—C17—C16	118.76 (13)	C24—C25—H25	120.00
N1—C18—C19	119.61 (11)	C26—C25—H25	120.00
N1—C18—C23	118.92 (12)	C27—C26—H26	121.00
C19—C18—C23	121.47 (13)	C25—C26—H26	121.00
C18—C19—C20	118.93 (13)	C27—C28—H28	121.00
C19—C20—C21	119.92 (15)	C29—C28—H28	121.00
C20—C21—C22	120.50 (15)	C24—C29—H29	119.00
C21—C22—C23	120.18 (15)	C28—C29—H29	119.00
C5—N1—C2—N3	−0.42 (15)	C5—C6—C7—C8	−179.24 (14)
C5—N1—C2—C24	−179.84 (12)	C11—C6—C7—C8	1.8 (2)
C18—N1—C2—N3	−172.89 (12)	C5—C6—C11—N10	178.39 (13)
C18—N1—C2—C24	7.7 (2)	C5—C6—C11—C12	−2.95 (19)
C2—N1—C5—C4	0.35 (14)	C7—C6—C11—N10	−2.6 (2)
C2—N1—C5—C6	−178.18 (14)	C7—C6—C11—C12	176.11 (13)
C18—N1—C5—C4	172.74 (12)	C6—C7—C8—C9	0.0 (2)
C18—N1—C5—C6	−5.8 (2)	C7—C8—C9—N10	−1.4 (3)
C2—N1—C18—C19	−107.55 (15)	N10—C11—C12—N13	0.22 (19)
C2—N1—C18—C23	72.48 (17)	N10—C11—C12—C17	179.47 (13)
C5—N1—C18—C19	81.51 (17)	C6—C11—C12—N13	−178.51 (13)
C5—N1—C18—C23	−98.46 (16)	C6—C11—C12—C17	0.7 (2)
C4—N3—C2—N1	0.29 (15)	N13—C12—C17—C4	−179.27 (13)
C4—N3—C2—C24	179.73 (12)	N13—C12—C17—C16	1.9 (2)
C2—N3—C4—C5	−0.05 (14)	C11—C12—C17—C4	1.5 (2)
C2—N3—C4—C17	179.34 (13)	C11—C12—C17—C16	−177.36 (13)
C11—N10—C9—C8	0.8 (2)	N13—C14—C15—C16	1.5 (3)
C9—N10—C11—C6	1.3 (2)	C14—C15—C16—C17	−2.1 (2)
C9—N10—C11—C12	−177.42 (14)	C15—C16—C17—C4	−178.24 (14)
C14—N13—C12—C11	176.69 (13)	C15—C16—C17—C12	0.6 (2)
C14—N13—C12—C17	−2.6 (2)	N1—C18—C19—C20	179.50 (13)
C12—N13—C14—C15	0.9 (2)	C23—C18—C19—C20	−0.5 (2)
N1—C2—C24—C25	33.4 (2)	N1—C18—C23—C22	−179.07 (13)
N1—C2—C24—C29	−149.58 (14)	C19—C18—C23—C22	1.0 (2)
N3—C2—C24—C25	−146.01 (14)	C18—C19—C20—C21	−0.3 (2)
N3—C2—C24—C29	31.05 (19)	C19—C20—C21—C22	0.6 (3)
N3—C4—C5—N1	−0.20 (15)	C20—C21—C22—C23	−0.2 (3)
N3—C4—C5—C6	178.50 (12)	C21—C22—C23—C18	−0.6 (2)
C17—C4—C5—N1	−179.62 (12)	C2—C24—C25—C26	176.81 (13)
C17—C4—C5—C6	−0.9 (2)	C29—C24—C25—C26	−0.2 (2)
N3—C4—C17—C12	179.23 (13)	C2—C24—C29—C28	−177.09 (14)
N3—C4—C17—C16	−2.0 (2)	C25—C24—C29—C28	0.1 (2)
C5—C4—C17—C12	−1.4 (2)	C24—C25—C26—C27	0.4 (2)
C5—C4—C17—C16	177.37 (14)	C25—C26—C27—F4	178.94 (14)
N1—C5—C6—C7	2.4 (2)	C25—C26—C27—C28	−0.5 (2)
N1—C5—C6—C11	−178.60 (13)	F4—C27—C28—C29	−179.07 (15)
C4—C5—C6—C7	−175.86 (14)	C26—C27—C28—C29	0.3 (3)
C4—C5—C6—C11	3.10 (19)	C27—C28—C29—C24	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N10i	0.96 (3)	2.62 (3)	3.282 (2)	127 (2)
O1W—H1W···N13i	0.96 (3)	1.97 (3)	2.902 (2)	163 (3)
O1W—H2W···F4ii	0.92 (4)	2.41 (3)	3.159 (2)	139 (3)
C9—H9···F4iii	0.95	2.49	3.248 (2)	136
C14—H14···O1Wiv	0.95	2.56	3.510 (2)	176
C19—H19···N3v	0.95	2.61	3.5209 (19)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N10i	0.96 (3)	2.62 (3)	3.282 (2)	127 (2)
O1W—H1W⋯N13i	0.96 (3)	1.97 (3)	2.902 (2)	163 (3)
O1W—H2W⋯F4ii	0.92 (4)	2.41 (3)	3.159 (2)	139 (3)
C9—H9⋯F4iii	0.95	2.49	3.248 (2)	136
C14—H14⋯O1Wiv	0.95	2.56	3.510 (2)	176
C19—H19⋯N3v	0.95	2.61	3.5209 (19)	162

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