(2E)-2-Benzyl-idene-9-phenyl-3,4-di-hydro-acridin-1(2H)-one.

In the title compound, C26H19NO, the plane of the aromatic heterocycle makes a dihedral angle of 75.22 (4)° with that of the attached phenyl ring. In the crystal, mol-ecules are connected by C-H⋯O inter-actions, generating R 2 (2)(12) dimers. These dimers are further connected by C-H⋯π inter-actions, linking the mol-ecules into chains running along the a-axis direction.

Related literature

For background to acridines, see: Kumar et al. (2012 ▶). For the biological activity of acridine derivatives, see: Pigatto et al. (2011 ▶); Das et al. (2011 ▶); Kumar et al. (2012 ▶); Prommier et al. (2006 ▶) Denny et al. (1982 ▶); Baguley & Ferguson (1998 ▶). For the synthesis of acridines, see: Tomar et al. (2010 ▶). For related structures, see: Buckleton & Waters (1984 ▶); Chantrapromma et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H19NO

M = 361.42

Monoclinic,

a = 9.2222 (3) Å

b = 10.7555 (4) Å

c = 19.4962 (5) Å

β = 95.503 (2)°

V = 1924.90 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.662, T max = 0.746

18382 measured reflections

4776 independent reflections

3205 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.00

4776 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814015943/bt6954sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015943/bt6954Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015943/bt6954Isup3.cml

CCDC reference: 1012814

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H19NO	F(000) = 760
Mr = 361.42	Dx = 1.247 Mg m−3Dm = 1.25 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4776 reflections
a = 9.2222 (3) Å	θ = 2.1–28.3°
b = 10.7555 (4) Å	µ = 0.08 mm−1
c = 19.4962 (5) Å	T = 293 K
β = 95.503 (2)°	Block, white
V = 1924.90 (11) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4776 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→10
Tmin = 0.662, Tmax = 0.746	k = −13→14
18382 measured reflections	l = −25→25

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3326P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.013
4776 reflections	Δρmax = 0.23 e Å−3
254 parameters	Δρmin = −0.16 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: 0.0041 (8)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
C1	0.47972 (17)	0.49247 (14)	0.17309 (8)	0.0542 (4)
H1	0.4841	0.4062	0.1757	0.065*
C2	0.5587 (2)	0.56214 (17)	0.22142 (9)	0.0711 (5)
H2	0.6162	0.5233	0.2569	0.085*
C3	0.5539 (2)	0.69204 (17)	0.21798 (10)	0.0811 (6)
H3	0.6089	0.7388	0.2511	0.097*
C4	0.4701 (2)	0.75058 (15)	0.16689 (9)	0.0677 (5)
H4	0.4674	0.8370	0.1655	0.081*
C5	0.38702 (16)	0.68116 (12)	0.11582 (7)	0.0457 (3)
C6	0.39092 (15)	0.54970 (12)	0.11883 (7)	0.0416 (3)
C7	0.30846 (14)	0.48187 (11)	0.06585 (6)	0.0376 (3)
C8	0.23412 (14)	0.54820 (11)	0.01290 (6)	0.0381 (3)
C9	0.23927 (14)	0.68112 (11)	0.01406 (7)	0.0399 (3)
C10	0.15959 (17)	0.75179 (12)	−0.04403 (7)	0.0484 (3)
H10A	0.1996	0.8350	−0.0456	0.058*
H10B	0.0577	0.7590	−0.0361	0.058*
C11	0.17193 (18)	0.68716 (12)	−0.11266 (7)	0.0502 (4)
H11A	0.1159	0.7328	−0.1490	0.060*
H11B	0.2730	0.6870	−0.1227	0.060*
C12	0.11714 (15)	0.55543 (12)	−0.11151 (7)	0.0434 (3)
C13	0.14319 (15)	0.48612 (11)	−0.04483 (6)	0.0399 (3)
C14	0.04150 (17)	0.49483 (12)	−0.16301 (7)	0.0475 (3)
H14	0.0134	0.4146	−0.1523	0.057*
C15	−0.00427 (18)	0.53472 (12)	−0.23384 (7)	0.0488 (3)
C16	0.0762 (2)	0.61459 (14)	−0.27197 (8)	0.0565 (4)
H16	0.1647	0.6460	−0.2525	0.068*
C17	0.0255 (2)	0.64745 (16)	−0.33848 (8)	0.0688 (5)
H17	0.0809	0.6998	−0.3635	0.083*
C18	−0.1053 (3)	0.60374 (18)	−0.36787 (9)	0.0773 (6)
H18	−0.1398	0.6280	−0.4122	0.093*
C19	−0.1857 (2)	0.52368 (18)	−0.33150 (9)	0.0739 (5)
H19	−0.2745	0.4935	−0.3515	0.089*
C20	−0.1349 (2)	0.48783 (15)	−0.26524 (8)	0.0601 (4)
H20	−0.1886	0.4319	−0.2415	0.072*
C21	0.31014 (14)	0.34287 (11)	0.06809 (6)	0.0398 (3)
C22	0.23121 (16)	0.27801 (12)	0.11307 (7)	0.0486 (3)
H22	0.1776	0.3208	0.1435	0.058*
C23	0.23196 (19)	0.14904 (14)	0.11288 (9)	0.0607 (4)
H23	0.1770	0.1056	0.1425	0.073*
C24	0.3134 (2)	0.08513 (14)	0.06919 (10)	0.0710 (5)
H24	0.3138	−0.0013	0.0691	0.085*
C25	0.3942 (2)	0.14968 (16)	0.02578 (10)	0.0766 (5)
H25	0.4509	0.1068	−0.0033	0.092*
C26	0.39204 (19)	0.27804 (14)	0.02481 (9)	0.0604 (4)
H26	0.4463	0.3209	−0.0053	0.072*
N1	0.31024 (13)	0.74545 (10)	0.06376 (6)	0.0459 (3)
O1	0.09155 (12)	0.38323 (8)	−0.03732 (5)	0.0517 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0594 (9)	0.0455 (8)	0.0552 (8)	0.0054 (7)	−0.0065 (7)	−0.0014 (6)
C2	0.0810 (12)	0.0635 (10)	0.0627 (10)	0.0080 (9)	−0.0252 (9)	−0.0038 (8)
C3	0.1013 (15)	0.0616 (11)	0.0722 (11)	0.0025 (10)	−0.0351 (11)	−0.0180 (9)
C4	0.0883 (13)	0.0435 (8)	0.0671 (10)	0.0003 (8)	−0.0153 (9)	−0.0135 (7)
C5	0.0519 (8)	0.0371 (7)	0.0476 (7)	0.0009 (6)	0.0017 (6)	−0.0063 (6)
C6	0.0442 (7)	0.0374 (7)	0.0431 (7)	0.0019 (6)	0.0029 (6)	−0.0019 (5)
C7	0.0401 (7)	0.0310 (6)	0.0421 (6)	0.0006 (5)	0.0059 (5)	0.0004 (5)
C8	0.0424 (7)	0.0301 (6)	0.0419 (7)	−0.0008 (5)	0.0045 (5)	0.0012 (5)
C9	0.0441 (7)	0.0298 (6)	0.0460 (7)	−0.0005 (5)	0.0054 (6)	0.0008 (5)
C10	0.0619 (9)	0.0281 (6)	0.0537 (8)	−0.0006 (6)	−0.0023 (7)	0.0052 (6)
C11	0.0655 (9)	0.0372 (7)	0.0470 (7)	−0.0054 (6)	0.0013 (7)	0.0077 (6)
C12	0.0527 (8)	0.0340 (6)	0.0434 (7)	0.0007 (6)	0.0039 (6)	0.0030 (5)
C13	0.0467 (7)	0.0299 (6)	0.0428 (7)	−0.0002 (5)	0.0028 (6)	0.0022 (5)
C14	0.0638 (9)	0.0346 (7)	0.0437 (7)	0.0006 (6)	0.0037 (6)	0.0023 (5)
C15	0.0669 (9)	0.0376 (7)	0.0415 (7)	0.0072 (7)	0.0042 (7)	−0.0024 (6)
C16	0.0744 (11)	0.0466 (8)	0.0493 (8)	0.0060 (7)	0.0093 (7)	0.0015 (7)
C17	0.1057 (15)	0.0537 (9)	0.0488 (9)	0.0118 (10)	0.0160 (10)	0.0080 (7)
C18	0.1155 (17)	0.0686 (12)	0.0457 (9)	0.0241 (11)	−0.0039 (10)	0.0050 (8)
C19	0.0860 (13)	0.0770 (12)	0.0544 (10)	0.0099 (10)	−0.0154 (9)	−0.0101 (9)
C20	0.0771 (11)	0.0542 (9)	0.0477 (8)	−0.0002 (8)	0.0000 (8)	−0.0060 (7)
C21	0.0437 (7)	0.0315 (6)	0.0429 (7)	0.0038 (5)	−0.0031 (6)	0.0013 (5)
C22	0.0569 (9)	0.0395 (7)	0.0485 (8)	0.0022 (6)	0.0000 (6)	0.0072 (6)
C23	0.0715 (11)	0.0423 (8)	0.0648 (10)	−0.0094 (7)	−0.0124 (8)	0.0168 (7)
C24	0.0966 (14)	0.0291 (7)	0.0817 (12)	0.0063 (8)	−0.0204 (11)	0.0012 (8)
C25	0.1012 (15)	0.0443 (9)	0.0846 (13)	0.0234 (9)	0.0111 (11)	−0.0074 (9)
C26	0.0708 (10)	0.0422 (8)	0.0705 (10)	0.0103 (7)	0.0191 (8)	0.0008 (7)
N1	0.0549 (7)	0.0322 (5)	0.0499 (6)	0.0004 (5)	0.0015 (5)	−0.0035 (5)
O1	0.0673 (7)	0.0343 (5)	0.0514 (6)	−0.0106 (4)	−0.0052 (5)	0.0058 (4)

C1—C2	1.359 (2)	C13—O1	1.2191 (15)
C1—C6	1.4151 (19)	C14—C15	1.4689 (18)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.399 (2)	C15—C20	1.393 (2)
C2—H2	0.9300	C15—C16	1.395 (2)
C3—C4	1.356 (2)	C16—C17	1.381 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.411 (2)	C17—C18	1.369 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—N1	1.3682 (17)	C18—C19	1.377 (3)
C5—C6	1.4154 (18)	C18—H18	0.9300
C6—C7	1.4236 (17)	C19—C20	1.386 (2)
C7—C8	1.3818 (17)	C19—H19	0.9300
C7—C21	1.4957 (17)	C20—H20	0.9300
C8—C9	1.4304 (17)	C21—C26	1.3750 (19)
C8—C13	1.4949 (17)	C21—C22	1.3813 (19)
C9—N1	1.3132 (16)	C22—C23	1.387 (2)
C9—C10	1.4970 (18)	C22—H22	0.9300
C10—C11	1.522 (2)	C23—C24	1.373 (3)
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700	C24—C25	1.369 (3)
C11—C12	1.5051 (18)	C24—H24	0.9300
C11—H11A	0.9700	C25—C26	1.381 (2)
C11—H11B	0.9700	C25—H25	0.9300
C12—C14	1.3361 (18)	C26—H26	0.9300
C12—C13	1.4978 (17)
C2—C1—C6	120.76 (14)	O1—C13—C12	121.60 (12)
C2—C1—H1	119.6	C8—C13—C12	117.57 (11)
C6—C1—H1	119.6	C12—C14—C15	130.26 (13)
C1—C2—C3	120.33 (15)	C12—C14—H14	114.9
C1—C2—H2	119.8	C15—C14—H14	114.9
C3—C2—H2	119.8	C20—C15—C16	118.07 (14)
C4—C3—C2	120.80 (15)	C20—C15—C14	117.78 (14)
C4—C3—H3	119.6	C16—C15—C14	124.14 (14)
C2—C3—H3	119.6	C17—C16—C15	120.55 (17)
C3—C4—C5	120.37 (15)	C17—C16—H16	119.7
C3—C4—H4	119.8	C15—C16—H16	119.7
C5—C4—H4	119.8	C18—C17—C16	120.70 (18)
N1—C5—C4	117.62 (13)	C18—C17—H17	119.7
N1—C5—C6	123.01 (12)	C16—C17—H17	119.7
C4—C5—C6	119.32 (13)	C17—C18—C19	119.74 (16)
C1—C6—C5	118.43 (12)	C17—C18—H18	120.1
C1—C6—C7	123.37 (12)	C19—C18—H18	120.1
C5—C6—C7	118.18 (12)	C18—C19—C20	120.23 (18)
C8—C7—C6	118.02 (11)	C18—C19—H19	119.9
C8—C7—C21	122.74 (11)	C20—C19—H19	119.9
C6—C7—C21	119.20 (11)	C19—C20—C15	120.66 (17)
C7—C8—C9	119.39 (11)	C19—C20—H20	119.7
C7—C8—C13	122.29 (11)	C15—C20—H20	119.7
C9—C8—C13	118.27 (11)	C26—C21—C22	119.17 (13)
N1—C9—C8	123.48 (12)	C26—C21—C7	119.59 (12)
N1—C9—C10	117.68 (11)	C22—C21—C7	121.24 (12)
C8—C9—C10	118.84 (11)	C21—C22—C23	120.02 (14)
C9—C10—C11	111.14 (11)	C21—C22—H22	120.0
C9—C10—H10A	109.4	C23—C22—H22	120.0
C11—C10—H10A	109.4	C24—C23—C22	120.35 (16)
C9—C10—H10B	109.4	C24—C23—H23	119.8
C11—C10—H10B	109.4	C22—C23—H23	119.8
H10A—C10—H10B	108.0	C25—C24—C23	119.48 (15)
C12—C11—C10	111.30 (11)	C25—C24—H24	120.3
C12—C11—H11A	109.4	C23—C24—H24	120.3
C10—C11—H11A	109.4	C24—C25—C26	120.52 (17)
C12—C11—H11B	109.4	C24—C25—H25	119.7
C10—C11—H11B	109.4	C26—C25—H25	119.7
H11A—C11—H11B	108.0	C21—C26—C25	120.43 (16)
C14—C12—C13	115.98 (12)	C21—C26—H26	119.8
C14—C12—C11	126.86 (12)	C25—C26—H26	119.8
C13—C12—C11	117.09 (11)	C9—N1—C5	117.84 (11)
O1—C13—C8	120.83 (11)
C6—C1—C2—C3	−0.3 (3)	C14—C12—C13—O1	−3.7 (2)
C1—C2—C3—C4	0.4 (3)	C11—C12—C13—O1	173.38 (13)
C2—C3—C4—C5	−0.5 (3)	C14—C12—C13—C8	176.83 (12)
C3—C4—C5—N1	−176.88 (17)	C11—C12—C13—C8	−6.04 (18)
C3—C4—C5—C6	0.6 (3)	C13—C12—C14—C15	179.30 (14)
C2—C1—C6—C5	0.4 (2)	C11—C12—C14—C15	2.5 (3)
C2—C1—C6—C7	178.48 (15)	C12—C14—C15—C20	−148.09 (16)
N1—C5—C6—C1	176.83 (13)	C12—C14—C15—C16	33.2 (2)
C4—C5—C6—C1	−0.5 (2)	C20—C15—C16—C17	1.1 (2)
N1—C5—C6—C7	−1.4 (2)	C14—C15—C16—C17	179.87 (14)
C4—C5—C6—C7	−178.70 (14)	C15—C16—C17—C18	0.9 (3)
C1—C6—C7—C8	−175.42 (13)	C16—C17—C18—C19	−1.6 (3)
C5—C6—C7—C8	2.67 (18)	C17—C18—C19—C20	0.3 (3)
C1—C6—C7—C21	2.24 (19)	C18—C19—C20—C15	1.8 (3)
C5—C6—C7—C21	−179.67 (12)	C16—C15—C20—C19	−2.5 (2)
C6—C7—C8—C9	−1.66 (18)	C14—C15—C20—C19	178.72 (14)
C21—C7—C8—C9	−179.24 (12)	C8—C7—C21—C26	74.02 (18)
C6—C7—C8—C13	−179.36 (11)	C6—C7—C21—C26	−103.53 (15)
C21—C7—C8—C13	3.06 (19)	C8—C7—C21—C22	−106.21 (15)
C7—C8—C9—N1	−0.88 (19)	C6—C7—C21—C22	76.24 (16)
C13—C8—C9—N1	176.92 (12)	C26—C21—C22—C23	−1.8 (2)
C7—C8—C9—C10	179.33 (12)	C7—C21—C22—C23	178.44 (13)
C13—C8—C9—C10	−2.87 (18)	C21—C22—C23—C24	1.4 (2)
N1—C9—C10—C11	141.67 (13)	C22—C23—C24—C25	0.0 (3)
C8—C9—C10—C11	−38.53 (17)	C23—C24—C25—C26	−1.2 (3)
C9—C10—C11—C12	56.53 (17)	C22—C21—C26—C25	0.7 (2)
C10—C11—C12—C14	142.07 (15)	C7—C21—C26—C25	−179.55 (15)
C10—C11—C12—C13	−34.70 (18)	C24—C25—C26—C21	0.8 (3)
C7—C8—C13—O1	24.48 (19)	C8—C9—N1—C5	2.25 (19)
C9—C8—C13—O1	−153.24 (13)	C10—C9—N1—C5	−177.96 (12)
C7—C8—C13—C12	−156.08 (12)	C4—C5—N1—C9	176.28 (13)
C9—C8—C13—C12	26.19 (17)	C6—C5—N1—C9	−1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1i	0.97	2.58	3.2700 (18)	128
C26—H26···Cg1ii	0.93	2.71	3.577 (18)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1i	0.97	2.58	3.2700 (18)	128
C26—H26⋯Cg1ii	0.93	2.71	3.577 (18)	156

Symmetry codes: (i) ; (ii) .