2-[(Anilino)(2-nitro-phen-yl)meth-yl]cyclo-hexa-none.

In the title compound, C(19)H(20)N(2)O(3), the cyclo-hexa-none ring adopts a chair conformation with the amino-methyl group is positioned equatorially. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a ▶,b ▶). For the biological activity of β-amino ketones, see: Arend et al. (1998 ▶). For the anti-inflammatory and anti­microbial activity of β-amino ketones, see: Jadhav et al. (2008 ▶) and Kalluraya et al. (2001 ▶), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006 ▶); Samet et al. (2009 ▶); Azizi et al. (2006 ▶); Cordova (2004 ▶). For related structures, see: Eftekhari-Sis et al. (2012b ▶); Yuan et al. (2007 ▶); Fun et al. (2009 ▶).

Experimental

Crystal data

C19H20N2O3

M = 324.37

Monoclinic,

a = 9.0535 (8) Å

b = 11.9947 (7) Å

c = 17.2267 (15) Å

β = 117.355 (6)°

V = 1661.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.62 × 0.43 × 0.21 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.784, T max = 0.958

10888 measured reflections

3434 independent reflections

2210 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.160

S = 0.97

3434 reflections

221 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.23 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036859/fj2593sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036859/fj2593Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036859/fj2593Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812036859/fj2593Isup4.cml

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

C19H20N2O3	F(000) = 688
Mr = 324.37	Dx = 1.297 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10888 reflections
a = 9.0535 (8) Å	θ = 1.7–28.1°
b = 11.9947 (7) Å	µ = 0.09 mm−1
c = 17.2267 (15) Å	T = 296 K
β = 117.355 (6)°	Prism, colorless
V = 1661.5 (2) Å3	0.62 × 0.43 × 0.21 mm
Z = 4

Stoe IPDS 2 diffractometer	3434 independent reflections
Radiation source: fine-focus sealed tube	2210 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
rotation method scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −11→11
Tmin = 0.784, Tmax = 0.958	k = −15→14
10888 measured reflections	l = −21→20

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.099P)2] where P = (Fo2 + 2Fc2)/3
3434 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.79 e Å−3
16 restraints	Δρmin = −0.23 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
C1	0.3530 (2)	0.26145 (18)	0.22061 (12)	0.0453 (5)
H1	0.2966	0.3031	0.2482	0.054*
C2	0.2739 (2)	0.1473 (2)	0.19939 (13)	0.0505 (5)
C3	0.0911 (3)	0.1470 (3)	0.13652 (16)	0.0690 (7)
H3A	0.0301	0.1828	0.1635	0.083*
H3B	0.0522	0.0707	0.1229	0.083*
C4	0.0580 (3)	0.2080 (3)	0.05272 (15)	0.0731 (8)
H4A	0.1080	0.1670	0.0223	0.088*
H4B	−0.0610	0.2115	0.0149	0.088*
C5	0.1274 (3)	0.3236 (3)	0.07141 (16)	0.0730 (8)
H5A	0.0699	0.3667	0.0969	0.088*
H5B	0.1089	0.3592	0.0172	0.088*
C6	0.3130 (3)	0.3223 (2)	0.13399 (16)	0.0660 (7)
H6A	0.3532	0.3984	0.1468	0.079*
H6B	0.3713	0.2856	0.1059	0.079*
C7	0.5407 (2)	0.26636 (18)	0.28430 (12)	0.0429 (5)
H7	0.5759	0.3436	0.2840	0.052*
C8	0.5807 (2)	0.23927 (17)	0.37935 (12)	0.0414 (4)
C9	0.5888 (2)	0.31751 (17)	0.44110 (13)	0.0448 (5)
C10	0.6289 (3)	0.2903 (2)	0.52741 (15)	0.0574 (6)
H10	0.6344	0.3455	0.5666	0.069*
C11	0.6599 (3)	0.1815 (2)	0.55354 (16)	0.0655 (7)
H11	0.6837	0.1613	0.6102	0.079*
C12	0.6555 (3)	0.1022 (2)	0.49480 (16)	0.0636 (6)
H12	0.6772	0.0281	0.5123	0.076*
C13	0.6193 (3)	0.13097 (19)	0.41035 (14)	0.0531 (5)
H13	0.6209	0.0757	0.3729	0.064*
C14	0.8043 (2)	0.20265 (19)	0.28812 (12)	0.0455 (5)
C15	0.8911 (3)	0.3024 (2)	0.31590 (16)	0.0613 (6)
H15	0.8341	0.3686	0.3111	0.074*
C16	1.0631 (3)	0.3029 (3)	0.35075 (17)	0.0752 (8)
H16	1.1208	0.3698	0.3693	0.090*
C17	1.1495 (3)	0.2056 (3)	0.35827 (16)	0.0750 (9)
H17	1.2650	0.2063	0.3830	0.090*
C18	1.0634 (3)	0.1077 (3)	0.32882 (17)	0.0726 (8)
H18	1.1208	0.0422	0.3320	0.087*
C19	0.8934 (3)	0.1054 (2)	0.29467 (15)	0.0580 (6)
H19	0.8370	0.0381	0.2757	0.070*
N1	0.6308 (2)	0.19843 (17)	0.25075 (11)	0.0467 (4)
N2	0.5569 (2)	0.43539 (16)	0.41868 (13)	0.0545 (5)
O1	0.3490 (2)	0.06234 (15)	0.22935 (12)	0.0718 (5)
O2	0.4393 (2)	0.46052 (15)	0.34977 (12)	0.0711 (5)
O3	0.6465 (3)	0.50448 (17)	0.47103 (14)	0.0861 (6)
H1A	0.593 (3)	0.133 (2)	0.2363 (14)	0.046 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0372 (9)	0.0539 (13)	0.0416 (10)	0.0030 (8)	0.0155 (8)	0.0015 (9)
C2	0.0409 (10)	0.0643 (13)	0.0424 (11)	−0.0054 (8)	0.0158 (8)	0.0008 (9)
C3	0.0425 (11)	0.090 (2)	0.0587 (14)	−0.0105 (11)	0.0094 (10)	0.0033 (13)
C4	0.0445 (12)	0.115 (3)	0.0449 (12)	0.0038 (13)	0.0080 (10)	−0.0011 (13)
C5	0.0605 (14)	0.093 (2)	0.0534 (14)	0.0169 (13)	0.0157 (11)	0.0192 (13)
C6	0.0604 (13)	0.0680 (17)	0.0568 (14)	0.0042 (11)	0.0160 (11)	0.0186 (12)
C7	0.0384 (9)	0.0447 (11)	0.0438 (10)	−0.0013 (8)	0.0173 (8)	−0.0015 (9)
C8	0.0294 (8)	0.0471 (12)	0.0420 (10)	−0.0005 (7)	0.0116 (7)	−0.0023 (9)
C9	0.0356 (9)	0.0486 (12)	0.0474 (11)	0.0007 (8)	0.0166 (8)	−0.0039 (9)
C10	0.0526 (12)	0.0719 (17)	0.0474 (12)	0.0040 (10)	0.0226 (10)	−0.0071 (11)
C11	0.0619 (13)	0.086 (2)	0.0441 (11)	0.0112 (12)	0.0205 (10)	0.0105 (12)
C12	0.0692 (14)	0.0574 (16)	0.0569 (14)	0.0108 (11)	0.0227 (11)	0.0139 (12)
C13	0.0545 (11)	0.0482 (13)	0.0485 (11)	0.0039 (9)	0.0168 (9)	0.0007 (10)
C14	0.0387 (9)	0.0631 (14)	0.0350 (9)	−0.0016 (8)	0.0171 (8)	0.0002 (9)
C15	0.0499 (12)	0.0755 (17)	0.0601 (13)	−0.0119 (11)	0.0267 (10)	−0.0143 (12)
C16	0.0541 (14)	0.111 (2)	0.0618 (15)	−0.0289 (14)	0.0275 (12)	−0.0200 (15)
C17	0.0396 (11)	0.135 (3)	0.0495 (13)	−0.0052 (14)	0.0200 (10)	0.0048 (15)
C18	0.0518 (13)	0.104 (2)	0.0636 (15)	0.0196 (14)	0.0278 (11)	0.0205 (15)
C19	0.0481 (11)	0.0691 (16)	0.0570 (13)	0.0066 (10)	0.0243 (10)	0.0072 (11)
N1	0.0382 (8)	0.0505 (12)	0.0492 (10)	−0.0036 (7)	0.0184 (7)	−0.0092 (8)
N2	0.0535 (10)	0.0533 (12)	0.0605 (12)	−0.0005 (8)	0.0294 (9)	−0.0071 (9)
O1	0.0614 (10)	0.0610 (11)	0.0812 (12)	−0.0048 (7)	0.0226 (9)	0.0008 (9)
O2	0.0737 (11)	0.0559 (11)	0.0707 (11)	0.0117 (8)	0.0220 (9)	0.0046 (9)
O3	0.0958 (14)	0.0607 (12)	0.0903 (13)	−0.0195 (10)	0.0329 (11)	−0.0274 (10)

C1—C2	1.510 (3)	C9—N2	1.459 (3)
C1—C7	1.543 (2)	C10—C11	1.367 (4)
C1—C6	1.547 (3)	C10—H10	0.9300
C1—H1	0.9800	C11—C12	1.376 (4)
C2—O1	1.202 (3)	C11—H11	0.9300
C2—C3	1.505 (3)	C12—C13	1.380 (3)
C3—C4	1.521 (4)	C12—H12	0.9300
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C15	1.391 (3)
C4—C5	1.494 (4)	C14—C19	1.392 (3)
C4—H4A	0.9700	C14—N1	1.399 (2)
C4—H4B	0.9700	C15—C16	1.388 (3)
C5—C6	1.523 (3)	C15—H15	0.9300
C5—H5A	0.9700	C16—C17	1.378 (4)
C5—H5B	0.9700	C16—H16	0.9300
C6—H6A	0.9700	C17—C18	1.371 (4)
C6—H6B	0.9700	C17—H17	0.9300
C7—N1	1.448 (3)	C18—C19	1.373 (3)
C7—C8	1.541 (3)	C18—H18	0.9300
C7—H7	0.9800	C19—H19	0.9300
C8—C13	1.387 (3)	N1—H1A	0.85 (2)
C8—C9	1.395 (3)	N2—O2	1.214 (2)
C9—C10	1.398 (3)	N2—O3	1.219 (3)
C2—C1—C7	116.84 (17)	C9—C8—C7	124.96 (18)
C2—C1—C6	108.61 (18)	C8—C9—C10	123.4 (2)
C7—C1—C6	111.16 (16)	C8—C9—N2	121.02 (19)
C2—C1—H1	106.5	C10—C9—N2	115.56 (19)
C7—C1—H1	106.5	C11—C10—C9	119.2 (2)
C6—C1—H1	106.5	C11—C10—H10	120.4
O1—C2—C3	121.7 (2)	C9—C10—H10	120.4
O1—C2—C1	123.57 (18)	C10—C11—C12	119.0 (2)
C3—C2—C1	114.8 (2)	C10—C11—H11	120.5
C2—C3—C4	110.71 (19)	C12—C11—H11	120.5
C2—C3—H3A	109.5	C11—C12—C13	121.0 (2)
C4—C3—H3A	109.5	C11—C12—H12	119.5
C2—C3—H3B	109.5	C13—C12—H12	119.5
C4—C3—H3B	109.5	C12—C13—C8	122.4 (2)
H3A—C3—H3B	108.1	C12—C13—H13	118.8
C5—C4—C3	111.2 (2)	C8—C13—H13	118.8
C5—C4—H4A	109.4	C15—C14—C19	118.60 (19)
C3—C4—H4A	109.4	C15—C14—N1	121.8 (2)
C5—C4—H4B	109.4	C19—C14—N1	119.5 (2)
C3—C4—H4B	109.4	C16—C15—C14	119.8 (2)
H4A—C4—H4B	108.0	C16—C15—H15	120.1
C4—C5—C6	111.1 (2)	C14—C15—H15	120.1
C4—C5—H5A	109.4	C17—C16—C15	120.9 (3)
C6—C5—H5A	109.4	C17—C16—H16	119.6
C4—C5—H5B	109.4	C15—C16—H16	119.6
C6—C5—H5B	109.4	C18—C17—C16	119.3 (2)
H5A—C5—H5B	108.0	C18—C17—H17	120.4
C5—C6—C1	112.4 (2)	C16—C17—H17	120.4
C5—C6—H6A	109.1	C17—C18—C19	120.7 (3)
C1—C6—H6A	109.1	C17—C18—H18	119.6
C5—C6—H6B	109.1	C19—C18—H18	119.6
C1—C6—H6B	109.1	C18—C19—C14	120.7 (2)
H6A—C6—H6B	107.9	C18—C19—H19	119.6
N1—C7—C8	113.92 (16)	C14—C19—H19	119.6
N1—C7—C1	109.45 (16)	C14—N1—C7	121.03 (17)
C8—C7—C1	113.04 (15)	C14—N1—H1A	112.7 (14)
N1—C7—H7	106.6	C7—N1—H1A	114.4 (14)
C8—C7—H7	106.6	O2—N2—O3	122.8 (2)
C1—C7—H7	106.6	O2—N2—C9	118.52 (18)
C13—C8—C9	114.90 (19)	O3—N2—C9	118.7 (2)
C13—C8—C7	120.08 (18)
C7—C1—C2—O1	0.1 (3)	C8—C9—C10—C11	−1.0 (3)
C6—C1—C2—O1	126.8 (2)	N2—C9—C10—C11	179.8 (2)
C7—C1—C2—C3	−179.56 (18)	C9—C10—C11—C12	1.9 (3)
C6—C1—C2—C3	−52.9 (2)	C10—C11—C12—C13	−0.4 (4)
O1—C2—C3—C4	−125.0 (3)	C11—C12—C13—C8	−2.1 (4)
C1—C2—C3—C4	54.7 (3)	C9—C8—C13—C12	2.9 (3)
C2—C3—C4—C5	−55.0 (3)	C7—C8—C13—C12	−179.79 (19)
C3—C4—C5—C6	56.5 (3)	C19—C14—C15—C16	−1.2 (3)
C4—C5—C6—C1	−56.3 (3)	N1—C14—C15—C16	−178.5 (2)
C2—C1—C6—C5	52.8 (3)	C14—C15—C16—C17	0.0 (4)
C7—C1—C6—C5	−177.3 (2)	C15—C16—C17—C18	1.6 (4)
C2—C1—C7—N1	56.4 (2)	C16—C17—C18—C19	−2.0 (4)
C6—C1—C7—N1	−69.0 (2)	C17—C18—C19—C14	0.8 (4)
C2—C1—C7—C8	−71.8 (2)	C15—C14—C19—C18	0.8 (3)
C6—C1—C7—C8	162.83 (19)	N1—C14—C19—C18	178.2 (2)
N1—C7—C8—C13	−32.7 (2)	C15—C14—N1—C7	−39.6 (3)
C1—C7—C8—C13	93.1 (2)	C19—C14—N1—C7	143.1 (2)
N1—C7—C8—C9	144.35 (18)	C8—C7—N1—C14	−63.0 (2)
C1—C7—C8—C9	−89.9 (2)	C1—C7—N1—C14	169.39 (18)
C13—C8—C9—C10	−1.4 (3)	C8—C9—N2—O2	44.2 (3)
C7—C8—C9—C10	−178.57 (17)	C10—C9—N2—O2	−136.5 (2)
C13—C8—C9—N2	177.87 (17)	C8—C9—N2—O3	−137.9 (2)
C7—C8—C9—N2	0.7 (3)	C10—C9—N2—O3	41.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.85 (2)	2.31 (2)	2.906 (3)	127.0 (18)
N1—H1A···O2i	0.85 (2)	2.48 (2)	3.246 (3)	150.2 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.85 (2)	2.31 (2)	2.906 (3)	127.0 (18)
N1—H1A⋯O2i	0.85 (2)	2.48 (2)	3.246 (3)	150.2 (19)

Symmetry code: (i) .