1-(4-Meth-oxy-phen-yl)-2-[4-(tri-fluoro-meth-yl)phen-yl]-1H-phenanthro[9,10-d]imidazole.

In the title compound, C29H19F3N2O, a phenanthroline-fused imidazole tetra-cyclic system, the fused benzene rings deviate slightly from the central ring and make dihedral angles with this ring of 3.47 (8) and 3.05 (8)°. The tri-fluoro-methyl-phenyl ring is roughly coplanar with the phenanthroline-fused imidazole tetra-cyclic system [dihedral angle = 11.02 (6)°], while the meth-oxy-phenyl ring is almost perpendicular [dihedral angle = 87.65 (6)°]. There are intra-molecular C-H ⋯π inter-actions involving the meth-oxy-phenyl ring and the central phenanthroline ring, as well as an inter-molecular C-H⋯π inter-action involving the phenanthroline ring. In addition, there is an inter-molecular π-π inter-action involving the central phenanthroline ring and the tri-fluoro-methyl-phenyl ring [centroid-centroid distance = 3.685 (2) Å], as well as C-H⋯N inter-actions linking the mol-ecules into dimers.

Related literature

For background to the supra­molecular architecture of phenanthroline compounds, see: Lehn (1995 ▶). For metal sensors, see: Walters et al. (2000 ▶). For mol­ecular electronics, see: Peng et al. (1997 ▶). For photo sensitizers see: Hara et al. (2001 ▶). For a related structure, see: Sathishkumar et al. (2013 ▶).

.

Experimental

Crystal data

C29H19F3N2O

M = 468.46

Monoclinic,

a = 11.7063 (9) Å

b = 20.2301 (16) Å

c = 9.5419 (8) Å

β = 99.725 (2)°

V = 2227.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.32 × 0.29 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.956, T max = 0.999

24449 measured reflections

5128 independent reflections

3511 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.01

5128 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 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 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019351/bv2223sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019351/bv2223Isup2.hkl

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

C29H19F3N2O	F(000) = 968
Mr = 468.46	Dx = 1.397 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5131 reflections
a = 11.7063 (9) Å	θ = 1.8–27.6°
b = 20.2301 (16) Å	µ = 0.10 mm−1
c = 9.5419 (8) Å	T = 173 K
β = 99.725 (2)°	Block, colourless
V = 2227.2 (3) Å3	0.32 × 0.29 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5128 independent reflections
Radiation source: fine-focus sealed tube	3511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Ω and φ scan	θmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→14
Tmin = 0.956, Tmax = 0.999	k = 0→26
24449 measured reflections	l = 0→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.6328P] where P = (Fo2 + 2Fc2)/3
5128 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.94082 (11)	−0.18352 (6)	0.83630 (17)	0.0945 (5)
F2	1.03787 (11)	−0.09609 (7)	0.88946 (19)	0.1026 (5)
F3	0.97313 (14)	−0.11886 (9)	0.67561 (17)	0.1112 (6)
O1	0.24682 (11)	−0.21387 (6)	0.47694 (14)	0.0615 (4)
N1	0.41440 (11)	0.01373 (6)	0.76779 (13)	0.0381 (3)
N2	0.53956 (11)	0.08671 (6)	0.88301 (14)	0.0414 (3)
C1	0.34962 (13)	0.06745 (7)	0.80056 (16)	0.0375 (3)
C2	0.22709 (13)	0.08118 (8)	0.77095 (16)	0.0404 (4)
C3	0.14290 (15)	0.04019 (9)	0.69130 (19)	0.0516 (4)
H3	0.1656	−0.0009	0.6565	0.062*
C4	0.02892 (16)	0.05872 (11)	0.6633 (2)	0.0625 (5)
H4	−0.0268	0.0306	0.6092	0.075*
C5	−0.00549 (16)	0.11848 (11)	0.7138 (2)	0.0674 (6)
H5	−0.0846	0.1313	0.6938	0.081*
C6	0.07410 (16)	0.15882 (10)	0.7921 (2)	0.0591 (5)
H6	0.0489	0.1995	0.8260	0.071*
C7	0.19225 (14)	0.14223 (8)	0.82452 (17)	0.0439 (4)
C8	0.27615 (14)	0.18711 (8)	0.90664 (17)	0.0435 (4)
C9	0.24350 (17)	0.24581 (9)	0.96904 (19)	0.0546 (4)
H9	0.1637	0.2571	0.9580	0.066*
C10	0.32367 (19)	0.28690 (9)	1.0449 (2)	0.0626 (5)
H10	0.2989	0.3260	1.0861	0.075*
C11	0.44104 (19)	0.27210 (9)	1.0624 (2)	0.0621 (5)
H11	0.4964	0.3011	1.1146	0.075*
C12	0.47650 (16)	0.21546 (8)	1.00403 (18)	0.0519 (4)
H12	0.5568	0.2053	1.0155	0.062*
C13	0.39540 (14)	0.17238 (7)	0.92748 (16)	0.0410 (4)
C14	0.42898 (13)	0.11102 (7)	0.87125 (16)	0.0387 (3)
C15	0.52887 (13)	0.02806 (7)	0.82138 (16)	0.0380 (3)
C16	0.63143 (13)	−0.01355 (7)	0.81555 (16)	0.0388 (3)
C17	0.62932 (15)	−0.07882 (8)	0.76912 (19)	0.0505 (4)
H17	0.5571	−0.1000	0.7379	0.061*
C18	0.73102 (16)	−0.11314 (9)	0.7679 (2)	0.0543 (4)
H18	0.7280	−0.1577	0.7360	0.065*
C19	0.83675 (14)	−0.08351 (8)	0.81246 (18)	0.0467 (4)
C20	0.84057 (15)	−0.01934 (9)	0.8612 (2)	0.0533 (4)
H20	0.9131	0.0013	0.8938	0.064*
C21	0.73894 (15)	0.01501 (8)	0.86267 (19)	0.0494 (4)
H21	0.7426	0.0592	0.8967	0.059*
C22	0.94602 (17)	−0.11998 (10)	0.8042 (2)	0.0606 (5)
C23	0.36937 (13)	−0.04529 (7)	0.69415 (16)	0.0374 (3)
C24	0.36221 (14)	−0.04960 (8)	0.54819 (17)	0.0434 (4)
H24	0.3855	−0.0135	0.4960	0.052*
C25	0.32095 (15)	−0.10681 (8)	0.47918 (18)	0.0482 (4)
H25	0.3165	−0.1102	0.3791	0.058*
C26	0.28607 (13)	−0.15923 (8)	0.55452 (18)	0.0450 (4)
C27	0.29213 (15)	−0.15426 (8)	0.70017 (19)	0.0502 (4)
H27	0.2676	−0.1901	0.7523	0.060*
C28	0.33403 (15)	−0.09708 (8)	0.76958 (18)	0.0460 (4)
H28	0.3384	−0.0936	0.8696	0.055*
C29	0.2023 (2)	−0.26684 (12)	0.5502 (3)	0.0963 (9)
H29A	0.1761	−0.3025	0.4830	0.144*
H29B	0.1369	−0.2510	0.5929	0.144*
H29C	0.2633	−0.2834	0.6251	0.144*

	U11	U22	U33	U12	U13	U23
F1	0.0725 (8)	0.0575 (8)	0.1538 (14)	0.0215 (6)	0.0206 (9)	0.0119 (8)
F2	0.0504 (7)	0.0934 (10)	0.1529 (14)	0.0193 (7)	−0.0148 (8)	−0.0329 (9)
F3	0.0985 (11)	0.1497 (14)	0.0970 (11)	0.0515 (10)	0.0497 (9)	0.0126 (10)
O1	0.0598 (8)	0.0564 (8)	0.0657 (8)	−0.0134 (6)	0.0028 (6)	−0.0200 (6)
N1	0.0384 (7)	0.0357 (6)	0.0391 (7)	−0.0013 (5)	0.0033 (5)	−0.0015 (5)
N2	0.0398 (7)	0.0414 (7)	0.0417 (7)	−0.0010 (6)	0.0033 (6)	−0.0023 (6)
C1	0.0414 (8)	0.0365 (8)	0.0347 (8)	−0.0008 (6)	0.0067 (6)	0.0039 (6)
C2	0.0397 (8)	0.0431 (8)	0.0383 (8)	−0.0010 (7)	0.0062 (6)	0.0059 (7)
C3	0.0422 (9)	0.0547 (10)	0.0570 (11)	−0.0020 (8)	0.0058 (8)	−0.0037 (8)
C4	0.0418 (10)	0.0735 (13)	0.0690 (13)	−0.0058 (9)	0.0002 (9)	−0.0066 (10)
C5	0.0391 (10)	0.0775 (14)	0.0831 (15)	0.0087 (10)	0.0035 (9)	0.0001 (12)
C6	0.0470 (10)	0.0600 (11)	0.0709 (13)	0.0087 (9)	0.0118 (9)	−0.0003 (10)
C7	0.0431 (9)	0.0467 (9)	0.0432 (9)	0.0031 (7)	0.0112 (7)	0.0065 (7)
C8	0.0504 (9)	0.0427 (8)	0.0392 (8)	0.0019 (7)	0.0127 (7)	0.0045 (7)
C9	0.0592 (11)	0.0505 (10)	0.0568 (11)	0.0083 (9)	0.0175 (9)	−0.0018 (8)
C10	0.0811 (14)	0.0501 (10)	0.0589 (12)	0.0058 (10)	0.0186 (10)	−0.0136 (9)
C11	0.0718 (13)	0.0532 (11)	0.0610 (12)	−0.0081 (10)	0.0102 (10)	−0.0159 (9)
C12	0.0549 (10)	0.0471 (9)	0.0536 (10)	−0.0038 (8)	0.0083 (8)	−0.0082 (8)
C13	0.0482 (9)	0.0392 (8)	0.0363 (8)	−0.0009 (7)	0.0086 (7)	0.0016 (6)
C14	0.0402 (8)	0.0379 (8)	0.0375 (8)	−0.0014 (7)	0.0054 (6)	0.0020 (6)
C15	0.0391 (8)	0.0395 (8)	0.0344 (8)	−0.0031 (7)	0.0033 (6)	0.0014 (6)
C16	0.0412 (8)	0.0412 (8)	0.0339 (8)	0.0003 (7)	0.0059 (6)	0.0029 (6)
C17	0.0427 (9)	0.0438 (9)	0.0625 (11)	−0.0007 (7)	0.0018 (8)	−0.0029 (8)
C18	0.0524 (10)	0.0424 (9)	0.0665 (12)	0.0042 (8)	0.0053 (9)	−0.0037 (8)
C19	0.0447 (9)	0.0482 (9)	0.0470 (9)	0.0067 (8)	0.0073 (7)	0.0049 (7)
C20	0.0404 (9)	0.0550 (10)	0.0629 (11)	0.0003 (8)	0.0040 (8)	−0.0046 (9)
C21	0.0458 (9)	0.0446 (9)	0.0562 (10)	−0.0001 (8)	0.0041 (8)	−0.0088 (8)
C22	0.0517 (11)	0.0564 (11)	0.0738 (14)	0.0082 (9)	0.0105 (10)	−0.0025 (10)
C23	0.0356 (8)	0.0366 (8)	0.0385 (8)	−0.0016 (6)	0.0023 (6)	−0.0017 (6)
C24	0.0452 (9)	0.0450 (9)	0.0388 (9)	−0.0016 (7)	0.0043 (7)	0.0057 (7)
C25	0.0504 (10)	0.0563 (10)	0.0355 (9)	0.0002 (8)	0.0003 (7)	−0.0043 (7)
C26	0.0357 (8)	0.0465 (9)	0.0503 (10)	−0.0025 (7)	0.0002 (7)	−0.0086 (7)
C27	0.0546 (10)	0.0447 (9)	0.0513 (10)	−0.0127 (8)	0.0091 (8)	0.0011 (8)
C28	0.0541 (10)	0.0470 (9)	0.0370 (8)	−0.0083 (8)	0.0081 (7)	−0.0012 (7)
C29	0.108 (2)	0.0749 (15)	0.112 (2)	−0.0536 (15)	0.0387 (16)	−0.0358 (14)

F1—C22	1.325 (2)	C11—H11	0.9500
F2—C22	1.325 (2)	C12—C13	1.400 (2)
F3—C22	1.319 (2)	C12—H12	0.9500
O1—C26	1.3661 (19)	C13—C14	1.433 (2)
O1—C29	1.425 (3)	C15—C16	1.475 (2)
N1—C15	1.3819 (19)	C16—C21	1.389 (2)
N1—C1	1.3907 (19)	C16—C17	1.392 (2)
N1—C23	1.4395 (19)	C17—C18	1.380 (2)
N2—C15	1.3209 (19)	C17—H17	0.9500
N2—C14	1.371 (2)	C18—C19	1.376 (2)
C1—C14	1.372 (2)	C18—H18	0.9500
C1—C2	1.441 (2)	C19—C20	1.377 (2)
C2—C3	1.408 (2)	C19—C22	1.490 (2)
C2—C7	1.423 (2)	C20—C21	1.380 (2)
C3—C4	1.368 (2)	C20—H20	0.9500
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.386 (3)	C23—C28	1.374 (2)
C4—H4	0.9500	C23—C24	1.384 (2)
C5—C6	1.363 (3)	C24—C25	1.378 (2)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.406 (2)	C25—C26	1.381 (2)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.464 (2)	C26—C27	1.383 (2)
C8—C13	1.408 (2)	C27—C28	1.381 (2)
C8—C9	1.410 (2)	C27—H27	0.9500
C9—C10	1.366 (3)	C28—H28	0.9500
C9—H9	0.9500	C29—H29A	0.9800
C10—C11	1.388 (3)	C29—H29B	0.9800
C10—H10	0.9500	C29—H29C	0.9800
C11—C12	1.369 (2)
C26—O1—C29	117.39 (15)	N1—C15—C16	127.66 (13)
C15—N1—C1	106.52 (12)	C21—C16—C17	117.66 (15)
C15—N1—C23	127.36 (12)	C21—C16—C15	116.69 (14)
C1—N1—C23	126.12 (13)	C17—C16—C15	125.64 (14)
C15—N2—C14	105.58 (13)	C18—C17—C16	120.74 (16)
C14—C1—N1	105.24 (13)	C18—C17—H17	119.6
C14—C1—C2	122.77 (14)	C16—C17—H17	119.6
N1—C1—C2	131.98 (14)	C19—C18—C17	120.69 (16)
C3—C2—C7	119.22 (15)	C19—C18—H18	119.7
C3—C2—C1	125.09 (15)	C17—C18—H18	119.7
C7—C2—C1	115.66 (14)	C18—C19—C20	119.41 (16)
C4—C3—C2	120.96 (17)	C18—C19—C22	120.21 (16)
C4—C3—H3	119.5	C20—C19—C22	120.36 (16)
C2—C3—H3	119.5	C19—C20—C21	119.95 (16)
C3—C4—C5	120.16 (18)	C19—C20—H20	120.0
C3—C4—H4	119.9	C21—C20—H20	120.0
C5—C4—H4	119.9	C20—C21—C16	121.52 (16)
C6—C5—C4	120.07 (18)	C20—C21—H21	119.2
C6—C5—H5	120.0	C16—C21—H21	119.2
C4—C5—H5	120.0	F3—C22—F2	105.49 (18)
C5—C6—C7	122.25 (18)	F3—C22—F1	105.03 (17)
C5—C6—H6	118.9	F2—C22—F1	106.03 (17)
C7—C6—H6	118.9	F3—C22—C19	112.60 (17)
C6—C7—C2	117.35 (16)	F2—C22—C19	113.69 (17)
C6—C7—C8	121.05 (16)	F1—C22—C19	113.25 (16)
C2—C7—C8	121.58 (14)	C28—C23—C24	120.45 (14)
C13—C8—C9	116.85 (16)	C28—C23—N1	119.65 (13)
C13—C8—C7	120.25 (14)	C24—C23—N1	119.91 (13)
C9—C8—C7	122.90 (16)	C25—C24—C23	119.38 (15)
C10—C9—C8	121.69 (18)	C25—C24—H24	120.3
C10—C9—H9	119.2	C23—C24—H24	120.3
C8—C9—H9	119.2	C24—C25—C26	120.45 (15)
C9—C10—C11	120.66 (17)	C24—C25—H25	119.8
C9—C10—H10	119.7	C26—C25—H25	119.8
C11—C10—H10	119.7	O1—C26—C25	116.18 (15)
C12—C11—C10	119.56 (18)	O1—C26—C27	123.97 (16)
C12—C11—H11	120.2	C25—C26—C27	119.85 (15)
C10—C11—H11	120.2	C28—C27—C26	119.76 (15)
C11—C12—C13	120.53 (18)	C28—C27—H27	120.1
C11—C12—H12	119.7	C26—C27—H27	120.1
C13—C12—H12	119.7	C23—C28—C27	120.10 (15)
C12—C13—C8	120.70 (15)	C23—C28—H28	120.0
C12—C13—C14	121.98 (15)	C27—C28—H28	120.0
C8—C13—C14	117.29 (14)	O1—C29—H29A	109.5
N2—C14—C1	111.17 (13)	O1—C29—H29B	109.5
N2—C14—C13	126.49 (14)	H29A—C29—H29B	109.5
C1—C14—C13	122.31 (14)	O1—C29—H29C	109.5
N2—C15—N1	111.48 (13)	H29A—C29—H29C	109.5
N2—C15—C16	120.86 (13)	H29B—C29—H29C	109.5
C15—N1—C1—C14	0.30 (16)	C8—C13—C14—C1	−0.5 (2)
C23—N1—C1—C14	179.48 (13)	C14—N2—C15—N1	0.87 (17)
C15—N1—C1—C2	179.13 (15)	C14—N2—C15—C16	−179.16 (13)
C23—N1—C1—C2	−1.7 (2)	C1—N1—C15—N2	−0.75 (16)
C14—C1—C2—C3	175.80 (16)	C23—N1—C15—N2	−179.92 (13)
N1—C1—C2—C3	−2.9 (3)	C1—N1—C15—C16	179.28 (14)
C14—C1—C2—C7	−2.3 (2)	C23—N1—C15—C16	0.1 (2)
N1—C1—C2—C7	179.08 (15)	N2—C15—C16—C21	−7.2 (2)
C7—C2—C3—C4	0.9 (3)	N1—C15—C16—C21	172.77 (15)
C1—C2—C3—C4	−177.09 (17)	N2—C15—C16—C17	171.79 (15)
C2—C3—C4—C5	−0.2 (3)	N1—C15—C16—C17	−8.2 (3)
C3—C4—C5—C6	−0.4 (3)	C21—C16—C17—C18	−1.2 (3)
C4—C5—C6—C7	0.2 (3)	C15—C16—C17—C18	179.86 (16)
C5—C6—C7—C2	0.6 (3)	C16—C17—C18—C19	−0.1 (3)
C5—C6—C7—C8	178.84 (18)	C17—C18—C19—C20	1.2 (3)
C3—C2—C7—C6	−1.1 (2)	C17—C18—C19—C22	−177.10 (18)
C1—C2—C7—C6	177.11 (15)	C18—C19—C20—C21	−1.1 (3)
C3—C2—C7—C8	−179.34 (15)	C22—C19—C20—C21	177.20 (17)
C1—C2—C7—C8	−1.2 (2)	C19—C20—C21—C16	−0.1 (3)
C6—C7—C8—C13	−174.43 (15)	C17—C16—C21—C20	1.3 (3)
C2—C7—C8—C13	3.8 (2)	C15—C16—C21—C20	−179.66 (16)
C6—C7—C8—C9	6.1 (2)	C18—C19—C22—F3	80.8 (2)
C2—C7—C8—C9	−175.70 (15)	C20—C19—C22—F3	−97.5 (2)
C13—C8—C9—C10	0.7 (3)	C18—C19—C22—F2	−159.34 (18)
C7—C8—C9—C10	−179.85 (17)	C20—C19—C22—F2	22.4 (3)
C8—C9—C10—C11	0.3 (3)	C18—C19—C22—F1	−38.2 (3)
C9—C10—C11—C12	−0.6 (3)	C20—C19—C22—F1	143.46 (19)
C10—C11—C12—C13	−0.2 (3)	C15—N1—C23—C28	92.07 (19)
C11—C12—C13—C8	1.3 (3)	C1—N1—C23—C28	−86.95 (19)
C11—C12—C13—C14	−176.70 (16)	C15—N1—C23—C24	−87.77 (19)
C9—C8—C13—C12	−1.5 (2)	C1—N1—C23—C24	93.20 (18)
C7—C8—C13—C12	179.04 (15)	C28—C23—C24—C25	−1.0 (2)
C9—C8—C13—C14	176.61 (14)	N1—C23—C24—C25	178.82 (14)
C7—C8—C13—C14	−2.9 (2)	C23—C24—C25—C26	0.5 (3)
C15—N2—C14—C1	−0.67 (17)	C29—O1—C26—C25	−175.49 (19)
C15—N2—C14—C13	177.31 (14)	C29—O1—C26—C27	4.5 (3)
N1—C1—C14—N2	0.23 (17)	C24—C25—C26—O1	−179.80 (15)
C2—C1—C14—N2	−178.74 (13)	C24—C25—C26—C27	0.2 (3)
N1—C1—C14—C13	−177.86 (13)	O1—C26—C27—C28	179.47 (16)
C2—C1—C14—C13	3.2 (2)	C25—C26—C27—C28	−0.6 (3)
C12—C13—C14—N2	−0.2 (2)	C24—C23—C28—C27	0.7 (2)
C8—C13—C14—N2	−178.24 (15)	N1—C23—C28—C27	−179.15 (15)
C12—C13—C14—C1	177.59 (15)	C26—C27—C28—C23	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N2i	0.95	2.55	3.402 (2)	150
C3—H3···Cg1	0.95	2.86	3.719 (2)	154
C10—H10···Cg2ii	0.95	2.69	3.419 (2)	136
C17—H17···Cg1	0.95	2.74	3.6042 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg are the centroids of the methoxyphenyl and phenthroline rings, repsectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯N2i	0.95	2.55	3.402 (2)	150
C3—H3⋯Cg1	0.95	2.86	3.719 (2)	154
C10—H10⋯Cg2ii	0.95	2.69	3.419 (2)	136
C17—H17⋯Cg1	0.95	2.74	3.6042 (2)	154

Symmetry codes: (i) ; (ii) .