(RS)-3-Acetyl-2-methyl-4-(3-nitro­phen­yl)-1,4,5,6,7,8-hexa­hydro­quinolin-5-one

Wang, D.; Wang, Y.; Turhong, M.

doi:10.1107/S160053680903832X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2561

doi:10.1107/S160053680903832X

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(RS)-3-Acetyl-2-methyl-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydroquinolin-5-one

Dong'e Wang,^a ^* Yu-zhou Wang ^a and Muhtar Turhong ^a ^*

^aDepartment of Chemistry, Kashgar Teachers' College, Kashgar 844000, People's Republic of China
^*Correspondence e-mail: m_turhong@126.com,

(Received 14 September 2009; accepted 22 September 2009; online 26 September 2009)

In the title compound, C₁₈H₁₈N₂O₄, the nitro group, a methyl group, the acetyl group and some atoms of the dihydroquinolinone group are disordered over two sites with the ratio of occupancies fixed at 0.57:0.43. The relationship between the major and minor components of disorder is that of diastereomers. In the crystal structure, intermolecular N—H⋯O, weak C—H⋯O and C—H⋯π interactions link the molecules into two-dimensional layers running parallel to the (010) plane.

Related literature

For the biological importance of polyhydroquinoline derivatives, see: Ko & Yao (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₈N₂O₄
M_r = 326.34
Monoclinic, P 2₁ /n
a = 8.5368 (5) Å
b = 17.0307 (6) Å
c = 11.4759 (5) Å
β = 106.143 (1)°
V = 1602.67 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.971, T_max = 0.990
9050 measured reflections
3151 independent reflections
1611 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.149
S = 0.90
3151 reflections
325 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.868 (10)	2.063 (13)	2.927 (8)	173 (2)
C6—H6⋯O4ⁱ	0.93	2.56	3.309 (16)	138
C18—H18A⋯O1ⁱ	0.96	2.46	3.239 (18)	138
C18—H18B⋯O3ⁱ	0.96	2.57	3.422 (15)	148
C11—H11A⋯O1ⁱⁱ	0.97	2.55	3.290 (16)	133
C12—H12A⋯Cg1ⁱⁱⁱ	0.97	2.76	3.71 (1)	166
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903832X/lh2906sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903832X/lh2906Isup2.hkl

checkCIF report

Comment top

Many polyhydroquinoline derivatives have been synthesized because of their biological importance (Ko & and Yao). In this paper, we report the crystal structure of the title compound, (I).

In the title molecule (Fig. 1), the nitro group, C18 methyl group, the acetyl group and some atoms of the dihydroquinolin-one (i.e. atoms C9-C12/C16-C18/O3/O4) are disordered over two positions with final site occupancies of 0.57:0.43 for the major and minor components, respectively. The bond lengths and angles are within normal ranges (Allen et al., 1987).

In the crystal structure, the molecules are first linked by one N2—H2A···O3 (-1/2+x,1/2-y,-1/2+z) hydrogen bond into a one-dimensional chain running parallel to the [101] direction (Table 1 and Fig. 2). These adjacent [101] chains are joined together by C11–H11A···O1 (x, y, -1+z) and C-H···π (C12···Cg1 =3.71 (1)Å, Cg1 is the centroid defined by atoms C1-C6 at (1/2+x,1/2-y,-1/2+z)) interactions, forming a two-dimensional layer structure running parallel to the (010) plane.

Related literature top

For the biological importance of polyhydroquinoline derivatives, see: Ko & Yao (2006). For bond-length data, see: Allen et al. (1987). Please check changes.

Experimental top

The title compound was synthesized according to a literature procedure (Ko & Yao, 2006). The product was recrystallized from ethyl acetate at room temperature to give block red crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The title molecule with the atom-numbering scheme, showing both the major (left) and minor (right) components. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal packing, showing the two-dimensional (010) layer. The weak hydrogen bonds and C—H···π interactions are shown as dashed lines. For the sake of clarity, the H atoms and disordered atoms not involved in the hydrogen-bonds pattern have been omitted.

(RS)-3-Acetyl-2-methyl-4-(3-nitrophenyl)-1,4,5,6,7,8- hexahydroquinolin-5-one top

Crystal data top

C₁₈H₁₈N₂O₄	F(000) = 688
M_r = 326.34	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1160 reflections
a = 8.5368 (5) Å	θ = 2.2–19.3°
b = 17.0307 (6) Å	µ = 0.10 mm⁻¹
c = 11.4759 (5) Å	T = 298 K
β = 106.143 (1)°	Block, yellow
V = 1602.67 (13) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3151 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
0.3° wide ω exposures scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.971, T_max = 0.990	k = −21→14
9050 measured reflections	l = −13→14

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²) + (0.0622P)²] where P = (F_o² + 2F_c²)/3
3151 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.34 e Å⁻³
12 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₄	V = 1602.67 (13) Å³
M_r = 326.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5368 (5) Å	µ = 0.10 mm⁻¹
b = 17.0307 (6) Å	T = 298 K
c = 11.4759 (5) Å	0.20 × 0.10 × 0.10 mm
β = 106.143 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3151 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1611 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.990	R_int = 0.094
9050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	12 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	Δρ_max = 0.34 e Å⁻³
3151 reflections	Δρ_min = −0.28 e Å⁻³
325 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.2737 (3)	0.20273 (14)	0.3479 (2)	0.0436 (6)
C2	0.3036 (3)	0.18309 (15)	0.4692 (2)	0.0491 (7)
H2	0.3974	0.2011	0.5255	0.059*
C3	0.1941 (4)	0.13684 (16)	0.5063 (2)	0.0543 (7)
C4	0.0532 (4)	0.10958 (16)	0.4267 (3)	0.0615 (8)
H4	−0.0197	0.0784	0.4532	0.074*
C5	0.0234 (3)	0.12982 (17)	0.3068 (3)	0.0621 (8)
H5	−0.0714	0.1123	0.2512	0.075*
C6	0.1317 (3)	0.17567 (16)	0.2676 (2)	0.0526 (7)
H6	0.1089	0.1886	0.1858	0.063*
C7	0.3954 (3)	0.25236 (15)	0.3038 (2)	0.0455 (7)
H7	0.4970	0.2547	0.3697	0.055*
C8	0.4336 (3)	0.21449 (16)	0.1960 (2)	0.0474 (7)
C9	0.545 (5)	0.151 (2)	0.220 (2)	0.053 (9)	0.57
C10	0.5914 (19)	0.1135 (11)	0.1123 (15)	0.075 (5)	0.57
H10A	0.6193	0.0587	0.1290	0.090*	0.57
H10B	0.6843	0.1402	0.0974	0.090*	0.57
C11	0.4385 (8)	0.1214 (3)	−0.0005 (4)	0.0700 (17)	0.57
H11A	0.4659	0.0995	−0.0704	0.084*	0.57
H11B	0.3515	0.0896	0.0139	0.084*	0.57
C12	0.3717 (10)	0.2063 (7)	−0.0331 (9)	0.039 (2)	0.57
H12A	0.4451	0.2365	−0.0668	0.047*	0.57
H12B	0.2651	0.2049	−0.0918	0.047*	0.57
O3	0.6237 (12)	0.1317 (7)	0.3215 (8)	0.044 (2)	0.57
C16	0.356 (2)	0.3899 (17)	0.3823 (18)	0.052 (7)	0.57
C17	0.2873 (9)	0.4703 (5)	0.3779 (6)	0.0517 (18)	0.57
H17A	0.3114	0.4913	0.4586	0.077*	0.57
H17B	0.1712	0.4684	0.3432	0.077*	0.57
H17C	0.3349	0.5033	0.3290	0.077*	0.57
C18	0.1732 (18)	0.4344 (7)	0.1111 (9)	0.050 (3)	0.57
H18A	0.0921	0.4436	0.1532	0.076*	0.57
H18B	0.1210	0.4288	0.0259	0.076*	0.57
H18C	0.2473	0.4780	0.1240	0.076*	0.57
O4	0.439 (3)	0.3647 (9)	0.4817 (13)	0.103 (6)	0.57
C9'	0.368 (3)	0.385 (2)	0.378 (2)	0.075 (14)	0.43
C10'	0.3390 (15)	0.4734 (9)	0.3478 (11)	0.085 (4)	0.43
H10C	0.4315	0.4959	0.3262	0.102*	0.43
H10D	0.3224	0.5019	0.4165	0.102*	0.43
C11'	0.1799 (10)	0.4766 (5)	0.2359 (8)	0.089 (3)	0.43
H11C	0.0919	0.4480	0.2550	0.107*	0.43
H11D	0.1456	0.5307	0.2184	0.107*	0.43
C12'	0.220 (3)	0.4386 (9)	0.1223 (14)	0.067 (6)	0.43
H12C	0.1249	0.4391	0.0524	0.081*	0.43
H12D	0.3080	0.4665	0.1022	0.081*	0.43
O3'	0.414 (3)	0.3620 (10)	0.4820 (15)	0.061 (4)	0.43
C16'	0.549 (7)	0.146 (2)	0.219 (3)	0.047 (12)	0.43
C17'	0.566 (2)	0.0938 (13)	0.1187 (17)	0.047 (4)	0.43
H17D	0.6219	0.1213	0.0696	0.071*	0.43
H17E	0.4592	0.0788	0.0698	0.071*	0.43
H17F	0.6261	0.0477	0.1522	0.071*	0.43
C18'	0.379 (2)	0.1953 (11)	−0.0320 (13)	0.105 (8)	0.43
H18D	0.4920	0.1827	−0.0213	0.158*	0.43
H18E	0.3405	0.2274	−0.1030	0.158*	0.43
H18F	0.3166	0.1477	−0.0416	0.158*	0.43
O4'	0.608 (2)	0.1250 (13)	0.3267 (16)	0.103 (6)	0.43
C13	0.3612 (3)	0.24079 (15)	0.0812 (2)	0.0454 (7)
C14	0.2679 (3)	0.35884 (16)	0.1597 (2)	0.0505 (7)
C15	0.3347 (3)	0.33563 (17)	0.2754 (2)	0.0517 (7)
N1	0.2306 (5)	0.1151 (2)	0.6349 (3)	0.0779 (9)
N2	0.2681 (3)	0.30700 (13)	0.06613 (18)	0.0510 (6)
H2A	0.227 (3)	0.3210 (14)	−0.0089 (11)	0.061*
O1	0.370 (2)	0.1286 (8)	0.7031 (14)	0.092 (3)	0.57
O2	0.123 (4)	0.0762 (16)	0.668 (3)	0.105 (6)	0.57
O1'	0.326 (3)	0.1589 (11)	0.7037 (19)	0.098 (4)	0.43
O2'	0.159 (5)	0.0643 (18)	0.665 (3)	0.098 (6)	0.43

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0465 (16)	0.0500 (16)	0.0340 (14)	0.0065 (13)	0.0109 (12)	−0.0020 (12)
C2	0.0530 (17)	0.0575 (18)	0.0384 (15)	0.0020 (13)	0.0151 (13)	−0.0041 (12)
C3	0.065 (2)	0.0602 (19)	0.0450 (17)	0.0081 (15)	0.0284 (15)	0.0028 (14)
C4	0.062 (2)	0.0566 (19)	0.075 (2)	0.0036 (15)	0.0347 (17)	−0.0002 (16)
C5	0.0481 (18)	0.074 (2)	0.061 (2)	−0.0052 (15)	0.0105 (15)	−0.0074 (16)
C6	0.0460 (17)	0.0666 (19)	0.0423 (16)	−0.0009 (14)	0.0072 (13)	0.0006 (13)
C7	0.0422 (15)	0.0610 (19)	0.0303 (14)	−0.0039 (13)	0.0053 (11)	−0.0003 (12)
C8	0.0433 (16)	0.0598 (19)	0.0401 (16)	−0.0037 (14)	0.0134 (12)	−0.0001 (13)
C9	0.045 (16)	0.072 (13)	0.039 (17)	−0.001 (11)	0.008 (12)	−0.009 (10)
C10	0.085 (8)	0.081 (10)	0.064 (6)	−0.013 (5)	0.031 (6)	−0.009 (6)
C11	0.107 (5)	0.068 (4)	0.030 (3)	0.019 (3)	0.011 (3)	−0.006 (3)
C12	0.039 (4)	0.043 (5)	0.039 (6)	−0.006 (3)	0.018 (4)	−0.004 (4)
O3	0.043 (3)	0.058 (4)	0.024 (4)	0.010 (3)	0.000 (3)	−0.010 (3)
C16	0.058 (9)	0.055 (12)	0.042 (13)	−0.007 (8)	0.014 (9)	−0.003 (9)
C17	0.058 (4)	0.055 (4)	0.042 (4)	−0.007 (4)	0.014 (3)	−0.003 (3)
C18	0.054 (9)	0.052 (5)	0.047 (4)	−0.007 (4)	0.016 (4)	0.0003 (3)
O4	0.145 (11)	0.097 (8)	0.048 (8)	0.009 (6)	−0.007 (6)	0.007 (5)
C9'	0.10 (2)	0.059 (19)	0.06 (2)	−0.018 (16)	0.015 (17)	−0.007 (14)
C10'	0.117 (10)	0.078 (7)	0.090 (8)	−0.001 (7)	0.078 (7)	0.007 (5)
C11'	0.088 (6)	0.067 (6)	0.113 (7)	0.018 (5)	0.031 (6)	−0.001 (5)
C12'	0.032 (8)	0.058 (8)	0.102 (10)	−0.009 (5)	0.003 (6)	−0.003 (6)
O3'	0.103 (7)	0.045 (7)	0.037 (9)	−0.001 (5)	0.023 (7)	−0.023 (6)
C16'	0.04 (2)	0.060 (16)	0.04 (2)	−0.004 (13)	0.013 (17)	0.000 (13)
C17'	0.043 (6)	0.060 (9)	0.040 (6)	−0.004 (6)	0.013 (5)	0.000 (5)
C18'	0.200 (16)	0.076 (13)	0.038 (10)	0.021 (11)	0.031 (9)	0.005 (8)
O4'	0.127 (12)	0.105 (11)	0.074 (10)	0.036 (9)	0.025 (8)	0.020 (7)
C13	0.0477 (16)	0.0515 (17)	0.0376 (15)	−0.0011 (13)	0.0132 (12)	0.0012 (12)
C14	0.0536 (18)	0.0520 (19)	0.0470 (17)	−0.0070 (14)	0.0160 (14)	−0.0003 (14)
C15	0.0582 (18)	0.0552 (19)	0.0418 (17)	−0.0071 (14)	0.0143 (14)	−0.0034 (14)
N1	0.089 (3)	0.091 (3)	0.063 (2)	0.003 (2)	0.0351 (19)	0.0093 (19)
N2	0.0605 (15)	0.0587 (15)	0.0303 (12)	0.0057 (12)	0.0068 (11)	0.0025 (11)
O1	0.104 (7)	0.126 (10)	0.046 (3)	0.004 (5)	0.021 (4)	0.016 (5)
O2	0.101 (9)	0.130 (9)	0.102 (7)	0.017 (5)	0.059 (5)	0.030 (5)
O1'	0.125 (13)	0.115 (12)	0.052 (5)	−0.003 (7)	0.023 (7)	−0.003 (7)
O2'	0.117 (17)	0.104 (11)	0.090 (8)	−0.015 (12)	0.058 (9)	0.044 (8)

Geometric parameters (Å, º) top

C1—C6	1.383 (3)	C17—H17C	0.9600
C1—C2	1.384 (3)	C18—C14	1.540 (12)
C1—C7	1.530 (3)	C18—H18A	0.9600
C2—C3	1.378 (4)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C3—C4	1.374 (4)	C9'—O3'	1.21 (3)
C3—N1	1.468 (4)	C9'—C15	1.41 (3)
C4—C5	1.372 (4)	C9'—C10'	1.54 (4)
C4—H4	0.9300	C10'—C11'	1.590 (13)
C5—C6	1.378 (4)	C10'—H10C	0.9700
C5—H5	0.9300	C10'—H10D	0.9700
C6—H6	0.9300	C11'—C12'	1.575 (14)
C7—C8	1.509 (3)	C11'—H11C	0.9700
C7—C15	1.514 (4)	C11'—H11D	0.9700
C7—H7	0.9800	C12'—C14	1.449 (14)
C8—C13	1.365 (3)	C12'—H12C	0.9700
C8—C9	1.41 (3)	C12'—H12D	0.9700
C8—C16'	1.51 (3)	C16'—O4'	1.25 (3)
C9—O3	1.22 (2)	C16'—C17'	1.49 (3)
C9—C10	1.54 (3)	C17'—H17D	0.9600
C10—C11	1.567 (14)	C17'—H17E	0.9600
C10—H10A	0.9700	C17'—H17F	0.9600
C10—H10B	0.9700	C18'—C13	1.558 (14)
C11—C12	1.562 (12)	C18'—H18D	0.9600
C11—H11A	0.9700	C18'—H18E	0.9600
C11—H11B	0.9700	C18'—H18F	0.9600
C12—C13	1.463 (10)	C13—N2	1.362 (3)
C12—H12A	0.9700	C14—C15	1.350 (3)
C12—H12B	0.9700	C14—N2	1.391 (3)
C16—O4	1.24 (2)	N1—O2'	1.17 (3)
C16—C17	1.48 (3)	N1—O1'	1.22 (3)
C16—C15	1.51 (3)	N1—O1	1.251 (19)
C17—H17A	0.9600	N1—O2	1.28 (2)
C17—H17B	0.9600	N2—H2A	0.868 (10)

C6—C1—C2	118.2 (2)	C9'—C10'—C11'	105.1 (13)
C6—C1—C7	120.9 (2)	C9'—C10'—H10C	110.7
C2—C1—C7	120.9 (2)	C11'—C10'—H10C	110.7
C3—C2—C1	119.9 (2)	C9'—C10'—H10D	110.7
C3—C2—H2	120.1	C11'—C10'—H10D	110.7
C1—C2—H2	120.1	H10C—C10'—H10D	108.8
C4—C3—C2	122.1 (3)	C12'—C11'—C10'	108.7 (10)
C4—C3—N1	119.0 (3)	C12'—C11'—H11C	110.0
C2—C3—N1	118.8 (3)	C10'—C11'—H11C	110.0
C5—C4—C3	117.8 (3)	C12'—C11'—H11D	110.0
C5—C4—H4	121.1	C10'—C11'—H11D	110.0
C3—C4—H4	121.1	H11C—C11'—H11D	108.3
C4—C5—C6	121.1 (3)	C14—C12'—C11'	104.4 (9)
C4—C5—H5	119.5	C14—C12'—H12C	110.9
C6—C5—H5	119.5	C11'—C12'—H12C	110.9
C5—C6—C1	121.0 (3)	C14—C12'—H12D	110.9
C5—C6—H6	119.5	C11'—C12'—H12D	110.9
C1—C6—H6	119.5	H12C—C12'—H12D	108.9
C8—C7—C15	111.3 (2)	O4'—C16'—C17'	120 (3)
C8—C7—C1	110.9 (2)	O4'—C16'—C8	117 (3)
C15—C7—C1	111.4 (2)	C17'—C16'—C8	122 (2)
C8—C7—H7	107.7	C16'—C17'—H17D	109.5
C15—C7—H7	107.7	C16'—C17'—H17E	109.5
C1—C7—H7	107.7	H17D—C17'—H17E	109.5
C13—C8—C9	122.5 (12)	C16'—C17'—H17F	109.5
C13—C8—C16'	121.4 (13)	H17D—C17'—H17F	109.5
C13—C8—C7	120.5 (3)	H17E—C17'—H17F	109.5
C9—C8—C7	117.0 (12)	C13—C18'—H18D	109.5
C16'—C8—C7	118.0 (13)	C13—C18'—H18E	109.5
O3—C9—C8	124 (2)	H18D—C18'—H18E	109.5
O3—C9—C10	117 (2)	C13—C18'—H18F	109.5
C8—C9—C10	118.2 (17)	H18D—C18'—H18F	109.5
C9—C10—C11	106.6 (18)	H18E—C18'—H18F	109.5
C9—C10—H10A	110.4	N2—C13—C8	119.1 (2)
C11—C10—H10A	110.4	N2—C13—C12	113.4 (5)
C9—C10—H10B	110.4	C8—C13—C12	127.5 (5)
C11—C10—H10B	110.4	N2—C13—C18'	119.7 (7)
H10A—C10—H10B	108.6	C8—C13—C18'	121.2 (7)
C12—C11—C10	116.2 (9)	C15—C14—N2	118.9 (3)
C12—C11—H11A	108.2	C15—C14—C12'	125.0 (7)
C10—C11—H11A	108.2	N2—C14—C12'	115.3 (7)
C12—C11—H11B	108.2	C15—C14—C18	129.5 (4)
C10—C11—H11B	108.2	N2—C14—C18	111.4 (4)
H11A—C11—H11B	107.4	C14—C15—C9'	125.2 (13)
C13—C12—C11	105.4 (6)	C14—C15—C16	122.9 (9)
C13—C12—H12A	110.7	C14—C15—C7	120.8 (2)
C11—C12—H12A	110.7	C9'—C15—C7	113.9 (13)
C13—C12—H12B	110.7	C16—C15—C7	116.3 (9)
C11—C12—H12B	110.7	O2'—N1—O1'	125 (2)
H12A—C12—H12B	108.8	O2'—N1—O1	116 (2)
O4—C16—C17	118 (2)	O1'—N1—O2	122.1 (19)
O4—C16—C15	116 (2)	O1—N1—O2	123.1 (17)
C17—C16—C15	125.6 (13)	O1'—N1—C3	114.4 (11)
C14—C18—H18A	109.5	O1—N1—C3	118.8 (8)
C14—C18—H18B	109.5	O2—N1—C3	117.7 (16)
C14—C18—H18C	109.5	C13—N2—C14	123.6 (2)
O3'—C9'—C15	124 (3)	C13—N2—H2A	114.5 (17)
O3'—C9'—C10'	122 (3)	C14—N2—H2A	120.3 (17)
C15—C9'—C10'	114.3 (19)

C6—C1—C2—C3	0.9 (4)	C11—C12—C13—C8	16.2 (7)
C7—C1—C2—C3	−178.5 (2)	C11'—C12'—C14—C15	−27.2 (16)
C1—C2—C3—C4	−0.7 (4)	C11'—C12'—C14—N2	163.7 (8)
C1—C2—C3—N1	178.4 (3)	N2—C14—C15—C9'	169.0 (11)
C2—C3—C4—C5	0.1 (4)	C12'—C14—C15—C9'	0.3 (15)
N1—C3—C4—C5	−179.0 (3)	C18—C14—C15—C9'	−17.2 (13)
C3—C4—C5—C6	0.3 (4)	N2—C14—C15—C16	173.7 (7)
C4—C5—C6—C1	0.0 (4)	C12'—C14—C15—C16	5.0 (13)
C2—C1—C6—C5	−0.6 (4)	C18—C14—C15—C16	−12.5 (11)
C7—C1—C6—C5	178.8 (2)	N2—C14—C15—C7	−5.3 (4)
C6—C1—C7—C8	−49.3 (3)	C12'—C14—C15—C7	−174.1 (10)
C2—C1—C7—C8	130.1 (2)	C18—C14—C15—C7	168.5 (7)
C6—C1—C7—C15	75.2 (3)	O3'—C9'—C15—C14	173.2 (14)
C2—C1—C7—C15	−105.4 (3)	C10'—C9'—C15—C14	−6.7 (19)
C15—C7—C8—C13	−23.7 (3)	C10'—C9'—C15—C7	168.0 (10)
C1—C7—C8—C13	100.9 (3)	O4—C16—C15—C14	−170.3 (11)
C15—C7—C8—C9	157 (2)	C17—C16—C15—C14	9.1 (16)
C1—C7—C8—C9	−79 (2)	O4—C16—C15—C7	8.8 (15)
C15—C7—C8—C16'	158 (3)	C17—C16—C15—C7	−171.9 (9)
C1—C7—C8—C16'	−77 (3)	C8—C7—C15—C14	22.7 (3)
C13—C8—C9—O3	172 (3)	C1—C7—C15—C14	−101.6 (3)
C16'—C8—C9—O3	−137 (100)	C8—C7—C15—C9'	−152.2 (10)
C7—C8—C9—O3	−8 (5)	C1—C7—C15—C9'	83.5 (10)
C13—C8—C9—C10	3 (5)	C8—C7—C15—C16	−156.4 (7)
C16'—C8—C9—C10	53 (100)	C1—C7—C15—C16	79.3 (7)
C7—C8—C9—C10	−178 (2)	C2—C3—N1—O2'	−165 (2)
O3—C9—C10—C11	158 (3)	C4—C3—N1—O1'	−158.8 (8)
C8—C9—C10—C11	−31 (4)	C2—C3—N1—O1'	22.1 (9)
C9—C10—C11—C12	56 (2)	C4—C3—N1—O1	168.2 (7)
C10—C11—C12—C13	−48.0 (10)	C2—C3—N1—O1	−10.9 (8)
O3'—C9'—C10'—C11'	−141.3 (17)	C4—C3—N1—O2	−5.0 (15)
C15—C9'—C10'—C11'	38.6 (16)	C2—C3—N1—O2	175.9 (15)
C9'—C10'—C11'—C12'	−67.2 (13)	C8—C13—N2—C14	13.6 (4)
C10'—C11'—C12'—C14	60.0 (14)	C12—C13—N2—C14	−165.8 (4)
C7—C8—C13—N2	7.2 (4)	C18'—C13—N2—C14	−168.1 (8)
C7—C8—C13—C12	−173.5 (5)	C15—C14—N2—C13	−14.6 (4)
C7—C8—C13—C18'	−171.1 (8)	C12'—C14—N2—C13	155.3 (9)
C11—C12—C13—N2	−164.5 (4)	C18—C14—N2—C13	170.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.87 (1)	2.06 (1)	2.927 (8)	173 (2)
C6—H6···O4ⁱ	0.93	2.56	3.309 (16)	138
C18—H18A···O1ⁱ	0.96	2.46	3.239 (18)	138
C18—H18B···O3ⁱ	0.96	2.57	3.422 (15)	148
C11—H11A···O1ⁱⁱ	0.97	2.55	3.290 (16)	133
C12—H12A···Cg1ⁱⁱⁱ	0.97	2.76	3.71 (1)	166

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y, z−1; (iii) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₄
M_r	326.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.5368 (5), 17.0307 (6), 11.4759 (5)
β (°)	106.143 (1)
V (Å³)	1602.67 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.971, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	9050, 3151, 1611
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.149, 0.90
No. of reflections	3151
No. of parameters	325
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.28

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.868 (10)	2.063 (13)	2.927 (8)	173 (2)
C6—H6···O4ⁱ	0.93	2.56	3.309 (16)	138.3
C18—H18A···O1ⁱ	0.96	2.46	3.239 (18)	138.3
C18—H18B···O3ⁱ	0.96	2.57	3.422 (15)	148.3
C11—H11A···O1ⁱⁱ	0.97	2.55	3.290 (16)	133.3
C12—H12A···Cg1ⁱⁱⁱ	0.97	2.76	3.71 (1)	166

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y, z−1; (iii) x+1/2, −y+1/2, z−1/2.

Acknowledgements

The authors thank Kashgar Teachers? College for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ko, S. K. & Yao, C. F. (2006). Tetrahedron, 62, 7293–7299. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Page o2561

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

(RS)-3-Acetyl-2-methyl-4-(3-nitro­phen­yl)-1,4,5,6,7,8-hexa­hydro­quinolin-5-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(RS)-3-Acetyl-2-methyl-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydroquinolin-5-one