9,9-Dimethyl-12-(3-nitro­phen­yl)-7,8,9,10,11,12-hexa­hydro­benz[a]acridin-11-one

Jia, R.; Peng, J.; Tu, S.

doi:10.1107/S1600536809033935

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2284

doi:10.1107/S1600536809033935

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9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin-11-one

Runhong Jia,^a Juhua Peng ^a and Shujiang Tu ^b ^*

^aLianyungang Teacher's College, Lianyungang 222006, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: jiarunhong@126.com

(Received 20 August 2009; accepted 25 August 2009; online 29 August 2009)

The title compound, C₂₅H₂₂N₂O₃, was synthesized by the reaction of 3-nitrobenzaldehyde, dimedone and 2-naphthylamine in ethanol. In the molecular structure, the cyclohexenone ring adopts an envelope conformation, whereas the piperidine ring has a boat conformation. The crystal packing is stabilized by intermolecular 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_r = 398.45
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.185
S = 1.01
3541 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

A lot of natural and synthetic compounds containing the acridine skeleton display interesting biological and physical activities, such as antimalaria (Wysocka-Skrzela et al. 1976) and antitumor agents (Matsumoto et al. 1983), and multihydroacridineone derivatives have been reported to have high fluorescence efficiency and can be used as fluorescent molecular probes for monitoring of polymerization process (Popielarz et al. 1997). They are also increasingly receiving attention due to their likeness in properties with those of 1,4-dihydropyridines, which have similarities in structure to the biologically important compounds such as NADH and NADPH (Srividya et al. 1996). As a consequence, the interest of organic chemists in the synthesis or structure modifications of acridinedione derivatives remains high. Microwave irradiation is a very useful technique in organic synthesis (Tu et al. 2002). It is a simple, timesaving, high yielding, and environmentally friendly process. We have already reported the synthesis of heterocyclic compounds under microwave irradiation (Tu et al. 2004). M. Kidwai and S. Rastogi have reported the synthesis of polyhydroacridinones without additional fused benzene rings (Kidwai et al. 2005). The efficiency of microwave irradiation in promoting organic reaction and the success of its application in heterocyclic synthesis (Jia et al. 2007) has rapidly gained in popularity. Therefore design and synthesis of these compounds has been challenging. For these reasons, the synthesis of compounds containing cyanopyridine derivatives is strongly desired. In this paper we report the crystal structure of the title compound (I).

In the crystal structure, the dihedral angle between the C1/C6/C8/C17/N1 plane and the C20—C25 benzene ring is 83.5 (8)° (Fig. 1). The dihedral angle between the C1/C6/C8/C17/N1 plane and the C8/C9/C14/C15/C16/C17 plane is 5.8 (5)°. The dihedral angle between the C1/C6/C8/C17/N1 plane and the C1/C2/C4/C5/C6 plane is 11.4 (4)°, indicating that they are almost parallel. The distance between atom C3 and the mean plane C4/C5/C6/C1/C2 is 0.594 (6) Å, showing that the cyclohexenone ring adopts an envelope conformation. The newly formed piperidine ring has a boat conformation with the atoms N1 and C7 deviating from the plane C1/C6/C17/C8 by 0.098 (5) and 0.184 (6) Å, respectively, on the same direction. One chiral center exists in the title compound at C7. The centrosymmetric space group indicates the presence of equimolar enantiomers (S and R) in the crystal structure. The molecules are connected via N1—H1···O1 hydrogen bonds, forming infinite one-dimensional chains along the b axis (Fig. 2).

Related literature top

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 is a very useful technique 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 top

Compound (I) was prepared by the reaction of 3-nitrobenzaldehyde (1 mmol), dimedone (1 mmol), 2-naphthylamine (1 mmol), in ethanol (2 ml) under microwave irradiation without catalyst. Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a 95% aqueous ethanol solution (yield 92%; m.p. 567–569 K). IR (cm^-1): 3260, 2928, 1582, 1522, 1494, 1385, 1234, 1155, 1093, 982, 923, 811, 729, 687, 654; ¹H NMR (DMSO-d₆): 0.82 (s, 3H, CH3), 1.06 (s, 3H, CH3), 2.04 (d, 1H, J = 16.0 Hz, CH), 2.25 (d, 1H, J = 16.0 Hz, CH), 2.43 (d, 1H, J = 16.4 Hz, CH), 2.58 (d, 1H, J = 16.4 Hz, CH), 5.97 (s, 1H, CH), 7.48–7.31 (m, 4H, ArH), 7.70 (d, 1H, J = 7.6 Hz, ArH),7.96–7.82 (m, 4H, ArH), 8.07 (s, 1H, ArH), 9.90 (s, 1H, NH).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram of the title compound viewed along the a axis.

9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin- 11-one top

Crystal data top

C₂₅H₂₂N₂O₃	F(000) = 840
M_r = 398.45	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0662P)²] where P = (F_o² + 2F_c²)/3
3541 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₅H₂₂N₂O₃	V = 2013 (2) Å³
M_r = 398.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.264 (7) Å	µ = 0.09 mm⁻¹
b = 13.099 (9) Å	T = 298 K
c = 15.018 (10) Å	0.17 × 0.16 × 0.10 mm
β = 94.403 (10)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3541 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1401 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.991	R_int = 0.078
10293 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
3541 reflections	Δρ_min = −0.19 e Å⁻³
273 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂N₂O₃
M_r	398.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.264 (7), 13.099 (9), 15.018 (10)
β (°)	94.403 (10)
V (Å³)	2013 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.985, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10293, 3541, 1401
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.185, 1.01
No. of reflections	3541
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.13	2.937 (4)	155.5

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors thank the National Science Foundation of China (No. 20672090) and the Natural Science Foundation of Jiangsu Province (No. BK2006033) and the Graduate Foundation of Xuzhou Normal University (No. 08YLB031) for financial support.

References

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Volume 65| Part 9| September 2009| Page o2284

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

9,9-Di­methyl-12-(3-nitro­phen­yl)-7,8,9,10,11,12-hexa­hydro­benz[a]acridin-11-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin-11-one