3,3-Dimethyl-9-phenyl-3,4-dihydro-acridin-1(2H)-one.

In the mol-ecule of the title compound, C(21)H(19)NO, the terminal saturated six-membered ring of the dihydro-acridine unit adopts an envelope conformation, while the other two fused rings are nearly coplanar, with a dihedral angle of 2.61 (3)°. The coplanar ring system is oriented with respect to the phenyl ring at a dihedral angle of 74.58 (3)°. In the crystal structure, there is a C-H⋯π contact between the central ring of the dihydro-acridine system and the phenyl ring and a π-π contact between the two central rings [centroid-centroid distance = 3.809 (1) Å].

Related literature

For general background, see: Kalluraya & Sreenivasa (1998 ▶); Doube et al. (1998 ▶); Maguire et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H19NO

M = 301.37

Monoclinic,

a = 16.341 (3) Å

b = 11.3889 (18) Å

c = 18.772 (4) Å

β = 110.386 (14)°

V = 3274.8 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 298 (2) K

0.33 × 0.22 × 0.1 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.980, T max = 0.990

11268 measured reflections

3882 independent reflections

3032 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.143

S = 1.10

3882 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022083/hk2495sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022083/hk2495Isup2.hkl

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

C21H19NO	F000 = 1280
Mr = 301.37	Dx = 1.222 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1575 reflections
a = 16.341 (3) Å	θ = 2.2–28.0º
b = 11.3889 (18) Å	µ = 0.08 mm−1
c = 18.772 (4) Å	T = 298 (2) K
β = 110.386 (14)º	Block, colorless
V = 3274.8 (10) Å3	0.33 × 0.22 × 0.1 mm
Z = 8

Stoe IPDSII diffractometer	Rint = 0.044
rotation method scans	θmax = 28.0º
Absorption correction: numericalshape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)	θmin = 2.2º
Tmin = 0.980, Tmax = 0.990	h = −21→21
11268 measured reflections	k = −14→15
3882 independent reflections	l = −24→17
3032 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0491P)2 + 1.8747P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.061	(Δ/σ)max = 0.002
wR(F2) = 0.143	Δρmax = 0.24 e Å−3
S = 1.10	Δρmin = −0.25 e Å−3
3882 reflections	Extinction correction: none
208 parameters

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.

	x	y	z	Uiso*/Ueq
O1	0.81274 (12)	0.40574 (13)	−0.19111 (8)	0.0814 (5)
N1	0.88041 (9)	0.16743 (13)	0.03136 (8)	0.0490 (3)
C1	0.87761 (13)	0.08450 (15)	−0.08673 (11)	0.0533 (4)
H1A	0.8206	0.048	−0.1079	0.064*
H1B	0.9169	0.0277	−0.0535	0.064*
C2	0.91044 (11)	0.11403 (15)	−0.15138 (10)	0.0494 (4)
C3	0.90577 (17)	0.00459 (19)	−0.20010 (14)	0.0736 (6)
H3A	0.9239	0.0244	−0.2421	0.088*
H3B	0.8469	−0.0242	−0.219	0.088*
H3C	0.9436	−0.055	−0.1698	0.088*
C4	1.00438 (13)	0.1581 (2)	−0.12016 (13)	0.0681 (6)
H4A	1.0074	0.2267	−0.0897	0.082*
H4B	1.0236	0.1773	−0.1616	0.082*
H4C	1.0413	0.0979	−0.0896	0.082*
C5	0.85007 (13)	0.20855 (17)	−0.19917 (10)	0.0570 (4)
H5A	0.8728	0.234	−0.238	0.068*
H5B	0.7933	0.1736	−0.2249	0.068*
C6	0.83780 (12)	0.31480 (15)	−0.15688 (9)	0.0493 (4)
C7	0.85331 (10)	0.30320 (13)	−0.07363 (9)	0.0405 (3)
C8	0.84960 (9)	0.39807 (14)	−0.02880 (9)	0.0411 (3)
C9	0.83425 (10)	0.52170 (14)	−0.05688 (9)	0.0423 (3)
C10	0.90001 (12)	0.58667 (17)	−0.06880 (11)	0.0550 (4)
H10	0.9535	0.5517	−0.0623	0.066*
C11	0.88648 (13)	0.70308 (17)	−0.09023 (12)	0.0635 (5)
H11	0.9312	0.7465	−0.0973	0.076*
C12	0.80695 (14)	0.75516 (16)	−0.10110 (11)	0.0626 (5)
H12	0.7977	0.8333	−0.1162	0.075*
C13	0.74135 (13)	0.69126 (16)	−0.08949 (12)	0.0595 (5)
H13	0.6877	0.7264	−0.0968	0.071*
C14	0.75471 (11)	0.57519 (15)	−0.06710 (10)	0.0496 (4)
H14	0.7102	0.5327	−0.0589	0.06*
C15	0.86231 (10)	0.37692 (15)	0.04941 (9)	0.0436 (4)
C16	0.86349 (12)	0.46714 (19)	0.10169 (11)	0.0584 (5)
H16	0.8566	0.5449	0.0856	0.07*
C17	0.87457 (14)	0.4412 (2)	0.17538 (11)	0.0720 (6)
H17	0.8753	0.5013	0.2091	0.086*
C18	0.88480 (14)	0.3247 (2)	0.20068 (11)	0.0746 (6)
H18	0.8914	0.308	0.2509	0.09*
C19	0.88514 (13)	0.2360 (2)	0.15250 (11)	0.0640 (5)
H19	0.8919	0.159	0.17	0.077*
C20	0.87526 (10)	0.25947 (16)	0.07591 (9)	0.0464 (4)
C21	0.87064 (10)	0.18891 (14)	−0.04023 (9)	0.0429 (4)

	U11	U22	U33	U12	U13	U23
O1	0.1371 (15)	0.0625 (8)	0.0472 (7)	0.0205 (9)	0.0353 (8)	0.0142 (7)
N1	0.0525 (8)	0.0514 (8)	0.0475 (8)	0.0020 (6)	0.0228 (6)	0.0132 (6)
C1	0.0635 (11)	0.0421 (8)	0.0588 (10)	−0.0016 (8)	0.0269 (9)	0.0013 (8)
C2	0.0542 (9)	0.0484 (9)	0.0504 (9)	−0.0015 (8)	0.0241 (8)	−0.0063 (7)
C3	0.0902 (15)	0.0633 (12)	0.0775 (14)	−0.0042 (11)	0.0420 (12)	−0.0184 (11)
C4	0.0554 (11)	0.0764 (13)	0.0784 (14)	−0.0041 (10)	0.0310 (10)	−0.0112 (11)
C5	0.0679 (11)	0.0613 (11)	0.0427 (9)	−0.0011 (9)	0.0205 (8)	−0.0042 (8)
C6	0.0590 (10)	0.0507 (9)	0.0398 (8)	0.0030 (8)	0.0192 (7)	0.0076 (7)
C7	0.0420 (8)	0.0436 (8)	0.0388 (8)	0.0000 (6)	0.0177 (6)	0.0050 (6)
C8	0.0386 (7)	0.0455 (8)	0.0421 (8)	0.0000 (6)	0.0178 (6)	0.0053 (7)
C9	0.0469 (8)	0.0433 (8)	0.0384 (8)	−0.0016 (7)	0.0170 (6)	0.0009 (6)
C10	0.0464 (9)	0.0595 (11)	0.0592 (11)	−0.0024 (8)	0.0187 (8)	0.0118 (9)
C11	0.0650 (12)	0.0596 (11)	0.0626 (12)	−0.0196 (9)	0.0179 (9)	0.0093 (9)
C12	0.0777 (13)	0.0381 (9)	0.0645 (12)	−0.0062 (9)	0.0152 (10)	0.0042 (8)
C13	0.0607 (11)	0.0460 (9)	0.0703 (12)	0.0065 (8)	0.0211 (9)	0.0007 (9)
C14	0.0509 (9)	0.0445 (9)	0.0579 (10)	−0.0011 (7)	0.0245 (8)	0.0008 (8)
C15	0.0397 (8)	0.0541 (9)	0.0403 (8)	0.0025 (7)	0.0181 (6)	0.0028 (7)
C16	0.0604 (11)	0.0676 (12)	0.0499 (10)	0.0043 (9)	0.0225 (8)	−0.0059 (9)
C17	0.0737 (13)	0.0998 (17)	0.0458 (10)	0.0081 (12)	0.0249 (9)	−0.0129 (11)
C18	0.0731 (13)	0.1169 (19)	0.0388 (9)	0.0139 (13)	0.0258 (9)	0.0106 (11)
C19	0.0648 (11)	0.0863 (14)	0.0458 (10)	0.0096 (10)	0.0253 (8)	0.0206 (10)
C20	0.0419 (8)	0.0604 (10)	0.0409 (8)	0.0014 (7)	0.0195 (6)	0.0103 (7)
C21	0.0426 (8)	0.0447 (8)	0.0450 (8)	−0.0009 (6)	0.0198 (7)	0.0064 (7)

C1—C21	1.503 (2)	C9—C14	1.387 (2)
C1—C2	1.526 (2)	C10—C11	1.381 (3)
C1—H1A	0.97	C10—H10	0.93
C1—H1B	0.97	C11—C12	1.377 (3)
C2—C5	1.523 (3)	C11—H11	0.93
C2—C4	1.525 (3)	C12—C13	1.375 (3)
C2—C3	1.532 (3)	C12—H12	0.93
C3—H3A	0.96	C13—C14	1.381 (2)
C3—H3B	0.96	C13—H13	0.93
C3—H3C	0.96	C14—H14	0.93
C4—H4A	0.96	C15—C16	1.416 (2)
C4—H4B	0.96	C15—C20	1.417 (2)
C4—H4C	0.96	C16—C17	1.364 (3)
C5—C6	1.499 (2)	C16—H16	0.93
C5—H5A	0.97	C17—C18	1.399 (3)
C5—H5B	0.97	C17—H17	0.93
C6—O1	1.212 (2)	C18—C19	1.357 (3)
C6—C7	1.499 (2)	C18—H18	0.93
C7—C8	1.384 (2)	C19—C20	1.415 (2)
C7—C21	1.430 (2)	C19—H19	0.93
C8—C15	1.430 (2)	C20—N1	1.362 (2)
C8—C9	1.494 (2)	C21—N1	1.320 (2)
C9—C10	1.386 (2)
C21—C1—C2	113.98 (14)	C10—C9—C8	121.06 (15)
C21—C1—H1A	108.8	C14—C9—C8	119.80 (14)
C2—C1—H1A	108.8	C11—C10—C9	120.35 (18)
C21—C1—H1B	108.8	C11—C10—H10	119.8
C2—C1—H1B	108.8	C9—C10—H10	119.8
H1A—C1—H1B	107.7	C12—C11—C10	120.24 (17)
C5—C2—C4	110.65 (16)	C12—C11—H11	119.9
C5—C2—C1	106.81 (14)	C10—C11—H11	119.9
C4—C2—C1	110.65 (16)	C13—C12—C11	119.75 (17)
C5—C2—C3	109.63 (16)	C13—C12—H12	120.1
C4—C2—C3	109.35 (16)	C11—C12—H12	120.1
C1—C2—C3	109.72 (15)	C12—C13—C14	120.38 (18)
C2—C3—H3A	109.5	C12—C13—H13	119.8
C2—C3—H3B	109.5	C14—C13—H13	119.8
H3A—C3—H3B	109.5	C13—C14—C9	120.24 (16)
C2—C3—H3C	109.5	C13—C14—H14	119.9
H3A—C3—H3C	109.5	C9—C14—H14	119.9
H3B—C3—H3C	109.5	C16—C15—C20	118.51 (16)
C2—C4—H4A	109.5	C16—C15—C8	123.45 (16)
C2—C4—H4B	109.5	C20—C15—C8	118.04 (15)
H4A—C4—H4B	109.5	C17—C16—C15	120.7 (2)
C2—C4—H4C	109.5	C17—C16—H16	119.7
H4A—C4—H4C	109.5	C15—C16—H16	119.7
H4B—C4—H4C	109.5	C16—C17—C18	120.5 (2)
C6—C5—C2	115.93 (15)	C16—C17—H17	119.7
C6—C5—H5A	108.3	C18—C17—H17	119.7
C2—C5—H5A	108.3	C19—C18—C17	120.46 (19)
C6—C5—H5B	108.3	C19—C18—H18	119.8
C2—C5—H5B	108.3	C17—C18—H18	119.8
H5A—C5—H5B	107.4	C18—C19—C20	120.8 (2)
O1—C6—C5	119.46 (16)	C18—C19—H19	119.6
O1—C6—C7	122.07 (16)	C20—C19—H19	119.6
C5—C6—C7	118.41 (15)	N1—C20—C19	117.99 (17)
C8—C7—C21	119.22 (14)	N1—C20—C15	123.00 (14)
C8—C7—C6	122.53 (14)	C19—C20—C15	119.00 (17)
C21—C7—C6	118.23 (14)	N1—C21—C7	123.40 (15)
C7—C8—C15	118.13 (14)	N1—C21—C1	115.98 (14)
C7—C8—C9	123.98 (14)	C7—C21—C1	120.62 (14)
C15—C8—C9	117.88 (14)	C21—N1—C20	118.11 (14)
C10—C9—C14	119.03 (15)
C21—C1—C2—C5	−55.2 (2)	C8—C9—C14—C13	176.85 (16)
C21—C1—C2—C4	65.3 (2)	C7—C8—C15—C16	177.41 (15)
C21—C1—C2—C3	−173.95 (17)	C9—C8—C15—C16	−1.8 (2)
C4—C2—C5—C6	−67.6 (2)	C7—C8—C15—C20	−1.9 (2)
C1—C2—C5—C6	52.9 (2)	C9—C8—C15—C20	178.84 (14)
C3—C2—C5—C6	171.73 (16)	C20—C15—C16—C17	−1.7 (3)
C2—C5—C6—O1	158.93 (18)	C8—C15—C16—C17	178.98 (17)
C2—C5—C6—C7	−23.8 (2)	C15—C16—C17—C18	−0.1 (3)
O1—C6—C7—C8	−7.4 (3)	C16—C17—C18—C19	1.0 (3)
C5—C6—C7—C8	175.35 (16)	C17—C18—C19—C20	0.1 (3)
O1—C6—C7—C21	171.17 (18)	C18—C19—C20—N1	176.85 (18)
C5—C6—C7—C21	−6.1 (2)	C18—C19—C20—C15	−1.9 (3)
C21—C7—C8—C15	−0.8 (2)	C16—C15—C20—N1	−176.02 (16)
C6—C7—C8—C15	177.79 (14)	C8—C15—C20—N1	3.4 (2)
C21—C7—C8—C9	178.40 (14)	C16—C15—C20—C19	2.7 (2)
C6—C7—C8—C9	−3.0 (2)	C8—C15—C20—C19	−177.96 (15)
C7—C8—C9—C10	−76.1 (2)	C8—C7—C21—N1	2.5 (2)
C15—C8—C9—C10	103.06 (18)	C6—C7—C21—N1	−176.10 (15)
C7—C8—C9—C14	107.68 (19)	C8—C7—C21—C1	−178.28 (15)
C15—C8—C9—C14	−73.2 (2)	C6—C7—C21—C1	3.1 (2)
C14—C9—C10—C11	0.3 (3)	C2—C1—C21—N1	−151.45 (15)
C8—C9—C10—C11	−175.97 (17)	C2—C1—C21—C7	29.3 (2)
C9—C10—C11—C12	−1.0 (3)	C7—C21—N1—C20	−1.2 (2)
C10—C11—C12—C13	0.9 (3)	C1—C21—N1—C20	179.53 (15)
C11—C12—C13—C14	−0.1 (3)	C19—C20—N1—C21	179.55 (15)
C12—C13—C14—C9	−0.7 (3)	C15—C20—N1—C21	−1.8 (2)
C10—C9—C14—C13	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1i	0.93	3.20	3.814 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C8/C15/C20/C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1i	0.93	3.20	3.814 (3)	126

Symmetry code: (i) .