9,9-Dimethyl-12-(3-nitro-phen-yl)-7,8,9,10,11,12-hexa-hydro-benz[a]acridin-11-one.

The title compound, C(25)H(22)N(2)O(3), was synthesized by the reaction of 3-nitro-benzaldehyde, dimedone and 2-naphthyl-amine in ethanol. In the mol-ecular structure, the cyclo-hexenone ring adopts an envelope conformation, whereas the piperidine ring has a boat conformation. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the biological and physical activity of compounds containing the acridine skeleton, see: Wysocka-Skrzela & Ledochowski (1976 ▶); Matsumoto et al. (1983 ▶); Popielarz et al. (1997 ▶). Jia et al. (2007 ▶); Kidwai & Rastogi (2005 ▶); Srividya et al. (1996 ▶). For microwave irradiation in organic synthesis, see: Tu et al. (2002 ▶, 2004 ▶). For related structures, see: Jia et al. (2006 ▶); Wang et al. (2006 ▶); Tu et al. (2006 ▶).

Experimental

Crystal data

C25H22N2O3

M = 398.45

Monoclinic,

a = 10.264 (7) Å

b = 13.099 (9) Å

c = 15.018 (10) Å

β = 94.403 (10)°

V = 2013 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.17 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.985, T max = 0.991

10293 measured reflections

3541 independent reflections

1401 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.185

S = 1.01

3541 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033935/zq2005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033935/zq2005Isup2.hkl

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

C25H22N2O3	F(000) = 840
Mr = 398.45	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Melting point = 567–569 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.264 (7) Å	Cell parameters from 1084 reflections
b = 13.099 (9) Å	θ = 2.5–22.0°
c = 15.018 (10) Å	µ = 0.09 mm−1
β = 94.403 (10)°	T = 298 K
V = 2013 (2) Å3	Block, colourless
Z = 4	0.17 × 0.16 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3541 independent reflections
Radiation source: fine-focus sealed tube	1401 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→11
Tmin = 0.985, Tmax = 0.991	k = −15→15
10293 measured reflections	l = −17→15

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3
3541 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
N1	0.1648 (3)	0.5920 (2)	0.2710 (2)	0.0467 (9)
H1	0.1878	0.5298	0.2818	0.056*
N2	−0.1766 (5)	0.6049 (4)	−0.0481 (3)	0.0780 (14)
O1	0.2576 (3)	0.9019 (2)	0.1356 (2)	0.0511 (8)
O2	−0.1419 (4)	0.5259 (4)	−0.0133 (3)	0.1142 (16)
O3	−0.2455 (6)	0.6095 (4)	−0.1163 (3)	0.154 (2)
C1	0.2442 (4)	0.6520 (3)	0.2254 (3)	0.0382 (10)
C2	0.3791 (4)	0.6138 (3)	0.2166 (3)	0.0473 (11)
H2A	0.3751	0.5409	0.2050	0.057*
H2B	0.4301	0.6238	0.2730	0.057*
C3	0.4497 (4)	0.6650 (3)	0.1429 (3)	0.0455 (11)
C4	0.4294 (4)	0.7796 (3)	0.1489 (3)	0.0517 (12)
H4A	0.4839	0.8052	0.1997	0.062*
H4B	0.4596	0.8109	0.0958	0.062*
C5	0.2909 (4)	0.8141 (3)	0.1584 (3)	0.0433 (11)
C6	0.2012 (4)	0.7453 (3)	0.1960 (3)	0.0353 (10)
C7	0.0640 (4)	0.7834 (3)	0.2070 (3)	0.0372 (10)
H7	0.0708	0.8533	0.2301	0.045*
C8	−0.0039 (4)	0.7197 (3)	0.2741 (3)	0.0391 (10)
C9	−0.1215 (4)	0.7545 (3)	0.3091 (3)	0.0415 (11)
C10	−0.1783 (4)	0.8501 (3)	0.2861 (3)	0.0493 (12)
H10	−0.1378	0.8931	0.2474	0.059*
C11	−0.2924 (4)	0.8803 (4)	0.3201 (3)	0.0644 (14)
H11	−0.3273	0.9442	0.3057	0.077*
C12	−0.3568 (5)	0.8154 (5)	0.3765 (4)	0.0744 (16)
H12	−0.4357	0.8353	0.3978	0.089*
C13	−0.3039 (5)	0.7236 (4)	0.4000 (3)	0.0653 (15)
H13	−0.3464	0.6818	0.4387	0.078*
C14	−0.1868 (4)	0.6900 (4)	0.3676 (3)	0.0520 (12)
C15	−0.1288 (5)	0.5958 (4)	0.3933 (3)	0.0618 (14)
H15	−0.1694	0.5544	0.4332	0.074*
C16	−0.0156 (4)	0.5643 (3)	0.3615 (3)	0.0529 (12)
H16	0.0207	0.5018	0.3792	0.063*
C17	0.0466 (4)	0.6269 (3)	0.3013 (3)	0.0423 (11)
C18	0.5955 (4)	0.6397 (3)	0.1543 (4)	0.0666 (15)
H18A	0.6306	0.6617	0.2122	0.100*
H18B	0.6400	0.6742	0.1091	0.100*
H18C	0.6073	0.5674	0.1488	0.100*
C19	0.3959 (4)	0.6251 (4)	0.0517 (3)	0.0666 (15)
H19A	0.4112	0.5530	0.0484	0.100*
H19B	0.4390	0.6591	0.0055	0.100*
H19C	0.3037	0.6382	0.0438	0.100*
C20	−0.0192 (4)	0.7865 (3)	0.1176 (3)	0.0354 (10)
C21	−0.0601 (4)	0.6960 (3)	0.0759 (3)	0.0404 (11)
H21	−0.0350	0.6334	0.1009	0.049*
C22	−0.1379 (4)	0.7000 (4)	−0.0025 (3)	0.0520 (12)
C23	−0.1796 (4)	0.7900 (5)	−0.0420 (3)	0.0643 (14)
H23	−0.2344	0.7903	−0.0942	0.077*
C24	−0.1373 (5)	0.8802 (4)	−0.0016 (3)	0.0660 (15)
H24	−0.1631	0.9425	−0.0269	0.079*
C25	−0.0565 (4)	0.8776 (3)	0.0769 (3)	0.0508 (12)
H25	−0.0267	0.9387	0.1027	0.061*

	U11	U22	U33	U12	U13	U23
N1	0.054 (2)	0.034 (2)	0.053 (2)	0.0032 (18)	0.0093 (19)	0.0036 (18)
N2	0.078 (3)	0.089 (4)	0.065 (3)	−0.042 (3)	−0.008 (3)	−0.005 (3)
O1	0.0500 (18)	0.0375 (18)	0.066 (2)	−0.0060 (15)	0.0069 (15)	0.0026 (16)
O2	0.118 (4)	0.078 (3)	0.141 (4)	−0.026 (3)	−0.029 (3)	−0.021 (3)
O3	0.222 (6)	0.148 (4)	0.079 (3)	−0.086 (4)	−0.072 (4)	0.013 (3)
C1	0.036 (3)	0.040 (3)	0.038 (3)	−0.004 (2)	−0.001 (2)	−0.003 (2)
C2	0.045 (3)	0.045 (3)	0.051 (3)	0.005 (2)	0.001 (2)	−0.002 (2)
C3	0.033 (3)	0.051 (3)	0.052 (3)	0.000 (2)	0.004 (2)	−0.001 (2)
C4	0.034 (3)	0.050 (3)	0.072 (3)	0.000 (2)	0.009 (2)	0.004 (3)
C5	0.043 (3)	0.043 (3)	0.043 (3)	−0.005 (2)	0.001 (2)	−0.007 (2)
C6	0.031 (2)	0.035 (2)	0.040 (3)	−0.0017 (19)	0.0066 (19)	−0.002 (2)
C7	0.036 (2)	0.033 (2)	0.042 (3)	0.000 (2)	0.005 (2)	−0.001 (2)
C8	0.038 (3)	0.046 (3)	0.034 (2)	−0.005 (2)	0.002 (2)	0.001 (2)
C9	0.038 (3)	0.051 (3)	0.036 (3)	−0.005 (2)	0.003 (2)	−0.005 (2)
C10	0.045 (3)	0.057 (3)	0.046 (3)	0.002 (2)	0.008 (2)	−0.002 (2)
C11	0.048 (3)	0.082 (4)	0.064 (4)	0.009 (3)	0.009 (3)	−0.010 (3)
C12	0.044 (3)	0.105 (5)	0.076 (4)	−0.003 (3)	0.018 (3)	−0.006 (4)
C13	0.053 (3)	0.090 (4)	0.055 (3)	−0.015 (3)	0.017 (3)	0.002 (3)
C14	0.040 (3)	0.070 (4)	0.047 (3)	−0.010 (3)	0.009 (2)	0.000 (3)
C15	0.068 (4)	0.066 (4)	0.053 (3)	−0.016 (3)	0.016 (3)	0.006 (3)
C16	0.062 (3)	0.049 (3)	0.048 (3)	−0.003 (2)	0.009 (3)	0.010 (2)
C17	0.047 (3)	0.041 (3)	0.040 (3)	−0.005 (2)	0.006 (2)	0.000 (2)
C18	0.041 (3)	0.067 (3)	0.092 (4)	0.005 (2)	0.005 (3)	0.000 (3)
C19	0.069 (4)	0.080 (4)	0.051 (3)	−0.003 (3)	0.010 (3)	−0.007 (3)
C20	0.029 (2)	0.039 (3)	0.038 (2)	0.004 (2)	0.0070 (19)	0.005 (2)
C21	0.036 (3)	0.045 (3)	0.041 (3)	−0.003 (2)	0.005 (2)	0.007 (2)
C22	0.046 (3)	0.072 (4)	0.039 (3)	−0.011 (3)	0.008 (2)	−0.001 (3)
C23	0.055 (3)	0.097 (4)	0.040 (3)	0.000 (3)	0.000 (2)	0.021 (3)
C24	0.070 (4)	0.074 (4)	0.054 (3)	0.024 (3)	0.006 (3)	0.020 (3)
C25	0.054 (3)	0.044 (3)	0.055 (3)	0.002 (2)	0.010 (2)	0.001 (2)

N1—C1	1.355 (5)	C10—H10	0.9300
N1—C17	1.405 (5)	C11—C12	1.401 (6)
N1—H1	0.8600	C11—H11	0.9300
N2—O3	1.201 (5)	C12—C13	1.355 (7)
N2—O2	1.201 (5)	C12—H12	0.9300
N2—C22	1.462 (6)	C13—C14	1.402 (6)
O1—C5	1.241 (5)	C13—H13	0.9300
C1—C6	1.361 (5)	C14—C15	1.411 (6)
C1—C2	1.489 (5)	C15—C16	1.355 (6)
C2—C3	1.524 (5)	C15—H15	0.9300
C2—H2A	0.9700	C16—C17	1.409 (5)
C2—H2B	0.9700	C16—H16	0.9300
C3—C4	1.520 (6)	C18—H18A	0.9600
C3—C18	1.529 (5)	C18—H18B	0.9600
C3—C19	1.529 (6)	C18—H18C	0.9600
C4—C5	1.508 (5)	C19—H19A	0.9600
C4—H4A	0.9700	C19—H19B	0.9600
C4—H4B	0.9700	C19—H19C	0.9600
C5—C6	1.435 (5)	C20—C25	1.381 (5)
C6—C7	1.515 (5)	C20—C21	1.391 (5)
C7—C8	1.518 (5)	C21—C22	1.372 (6)
C7—C20	1.535 (5)	C21—H21	0.9300
C7—H7	0.9800	C22—C23	1.374 (6)
C8—C17	1.371 (5)	C23—C24	1.382 (7)
C8—C9	1.428 (5)	C23—H23	0.9300
C9—C10	1.413 (6)	C24—C25	1.389 (6)
C9—C14	1.423 (6)	C24—H24	0.9300
C10—C11	1.372 (6)	C25—H25	0.9300
C1—N1—C17	122.9 (3)	C12—C11—H11	119.8
C1—N1—H1	118.6	C13—C12—C11	119.8 (5)
C17—N1—H1	118.6	C13—C12—H12	120.1
O3—N2—O2	123.3 (5)	C11—C12—H12	120.1
O3—N2—C22	118.6 (6)	C12—C13—C14	121.6 (5)
O2—N2—C22	118.0 (5)	C12—C13—H13	119.2
N1—C1—C6	119.5 (4)	C14—C13—H13	119.2
N1—C1—C2	116.7 (4)	C13—C14—C15	122.3 (5)
C6—C1—C2	123.6 (4)	C13—C14—C9	119.0 (5)
C1—C2—C3	114.4 (3)	C15—C14—C9	118.7 (4)
C1—C2—H2A	108.6	C16—C15—C14	121.7 (4)
C3—C2—H2A	108.6	C16—C15—H15	119.2
C1—C2—H2B	108.6	C14—C15—H15	119.2
C3—C2—H2B	108.6	C15—C16—C17	119.5 (4)
H2A—C2—H2B	107.6	C15—C16—H16	120.3
C4—C3—C2	108.4 (3)	C17—C16—H16	120.3
C4—C3—C18	110.2 (3)	C8—C17—N1	120.5 (4)
C2—C3—C18	109.8 (4)	C8—C17—C16	121.9 (4)
C4—C3—C19	110.5 (4)	N1—C17—C16	117.6 (4)
C2—C3—C19	109.9 (4)	C3—C18—H18A	109.5
C18—C3—C19	108.0 (4)	C3—C18—H18B	109.5
C5—C4—C3	115.9 (3)	H18A—C18—H18B	109.5
C5—C4—H4A	108.3	C3—C18—H18C	109.5
C3—C4—H4A	108.3	H18A—C18—H18C	109.5
C5—C4—H4B	108.3	H18B—C18—H18C	109.5
C3—C4—H4B	108.3	C3—C19—H19A	109.5
H4A—C4—H4B	107.4	C3—C19—H19B	109.5
O1—C5—C6	121.2 (4)	H19A—C19—H19B	109.5
O1—C5—C4	119.6 (4)	C3—C19—H19C	109.5
C6—C5—C4	119.2 (4)	H19A—C19—H19C	109.5
C1—C6—C5	119.3 (4)	H19B—C19—H19C	109.5
C1—C6—C7	122.7 (3)	C25—C20—C21	118.3 (4)
C5—C6—C7	117.8 (4)	C25—C20—C7	121.8 (4)
C6—C7—C8	111.7 (3)	C21—C20—C7	119.9 (4)
C6—C7—C20	111.8 (3)	C22—C21—C20	119.3 (4)
C8—C7—C20	110.0 (3)	C22—C21—H21	120.4
C6—C7—H7	107.7	C20—C21—H21	120.4
C8—C7—H7	107.7	C21—C22—C23	123.0 (5)
C20—C7—H7	107.7	C21—C22—N2	119.2 (5)
C17—C8—C9	119.0 (4)	C23—C22—N2	117.7 (5)
C17—C8—C7	120.2 (4)	C22—C23—C24	117.9 (4)
C9—C8—C7	120.8 (4)	C22—C23—H23	121.1
C10—C9—C14	118.2 (4)	C24—C23—H23	121.1
C10—C9—C8	122.5 (4)	C23—C24—C25	119.9 (5)
C14—C9—C8	119.3 (4)	C23—C24—H24	120.0
C11—C10—C9	120.8 (4)	C25—C24—H24	120.0
C11—C10—H10	119.6	C20—C25—C24	121.6 (4)
C9—C10—H10	119.6	C20—C25—H25	119.2
C10—C11—C12	120.5 (5)	C24—C25—H25	119.2
C10—C11—H11	119.8
C17—N1—C1—C6	−9.7 (6)	C11—C12—C13—C14	−1.5 (8)
C17—N1—C1—C2	165.8 (4)	C12—C13—C14—C15	178.3 (5)
N1—C1—C2—C3	162.1 (3)	C12—C13—C14—C9	0.5 (7)
C6—C1—C2—C3	−22.5 (6)	C10—C9—C14—C13	−0.1 (6)
C1—C2—C3—C4	45.8 (5)	C8—C9—C14—C13	−178.4 (4)
C1—C2—C3—C18	166.2 (4)	C10—C9—C14—C15	−178.0 (4)
C1—C2—C3—C19	−75.1 (5)	C8—C9—C14—C15	3.8 (6)
C2—C3—C4—C5	−47.4 (5)	C13—C14—C15—C16	180.0 (5)
C18—C3—C4—C5	−167.5 (4)	C9—C14—C15—C16	−2.3 (7)
C19—C3—C4—C5	73.1 (5)	C14—C15—C16—C17	0.2 (7)
C3—C4—C5—O1	−157.1 (4)	C9—C8—C17—N1	−177.4 (3)
C3—C4—C5—C6	24.7 (6)	C7—C8—C17—N1	3.1 (6)
N1—C1—C6—C5	171.8 (4)	C9—C8—C17—C16	1.3 (6)
C2—C1—C6—C5	−3.5 (6)	C7—C8—C17—C16	−178.2 (4)
N1—C1—C6—C7	−3.8 (6)	C1—N1—C17—C8	10.1 (6)
C2—C1—C6—C7	−179.0 (4)	C1—N1—C17—C16	−168.7 (4)
O1—C5—C6—C1	−175.7 (4)	C15—C16—C17—C8	0.3 (7)
C4—C5—C6—C1	2.5 (6)	C15—C16—C17—N1	179.0 (4)
O1—C5—C6—C7	0.1 (6)	C6—C7—C20—C25	−109.8 (4)
C4—C5—C6—C7	178.2 (4)	C8—C7—C20—C25	125.4 (4)
C1—C6—C7—C8	15.0 (5)	C6—C7—C20—C21	70.8 (4)
C5—C6—C7—C8	−160.6 (3)	C8—C7—C20—C21	−53.9 (5)
C1—C6—C7—C20	−108.8 (4)	C25—C20—C21—C22	−1.5 (6)
C5—C6—C7—C20	75.6 (4)	C7—C20—C21—C22	177.9 (4)
C6—C7—C8—C17	−14.3 (5)	C20—C21—C22—C23	−0.9 (6)
C20—C7—C8—C17	110.5 (4)	C20—C21—C22—N2	177.6 (4)
C6—C7—C8—C9	166.3 (3)	O3—N2—C22—C21	179.4 (5)
C20—C7—C8—C9	−68.9 (4)	O2—N2—C22—C21	2.4 (7)
C17—C8—C9—C10	178.5 (4)	O3—N2—C22—C23	−2.0 (7)
C7—C8—C9—C10	−2.0 (6)	O2—N2—C22—C23	−179.0 (5)
C17—C8—C9—C14	−3.3 (6)	C21—C22—C23—C24	2.0 (7)
C7—C8—C9—C14	176.2 (4)	N2—C22—C23—C24	−176.6 (4)
C14—C9—C10—C11	0.8 (6)	C22—C23—C24—C25	−0.6 (7)
C8—C9—C10—C11	179.0 (4)	C21—C20—C25—C24	2.8 (6)
C9—C10—C11—C12	−1.8 (7)	C7—C20—C25—C24	−176.6 (4)
C10—C11—C12—C13	2.2 (8)	C23—C24—C25—C20	−1.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.13	2.937 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.13	2.937 (4)	156

Symmetry code: (i) .