2-[Anilino(phen-yl)meth-yl]cyclo-heptan-one.

In the title compound, C20H23NO, the cyclo-hepta-none ring adopts a twist-chair conformation, with the amino-methyl substituent in an equatorial position. The relative configuration of the two stereocenters is R,R. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along [100].

Related literature

For the synthesis of title compound and related compounds, see: Eftekhari-Sis et al. (2013 ▶). For the biological activity of β-amino ketones, see: Arend et al. (1998 ▶); Jadhav et al. (2008 ▶); Kalluraya et al. (2001 ▶). For information on the Mannich reaction, see, for example: Eftekhari-Sis et al. (2006 ▶); Azizi et al. (2006 ▶); Cordova (2004 ▶). For the crystal structures of related compounds, see: Eftekhari-Sis et al. (2012 ▶); Yuan et al. (2007 ▶); Fun et al. (2009 ▶). For puckering parameters, see: Evans & Boeyens (1989 ▶).

Experimental

Crystal data

C20H23NO

M = 293.39

Monoclinic,

a = 5.7534 (4) Å

b = 16.1336 (8) Å

c = 18.1980 (13) Å

β = 99.371 (6)°

V = 1666.65 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.72 × 0.56 × 0.27 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.965, T max = 0.985

10757 measured reflections

3449 independent reflections

2170 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.01

3449 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.13 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, 2008) ▶; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050659/fy2069sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050659/fy2069Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050659/fy2069Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050659/fy2069Isup4.cml

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

C20H23NO	F(000) = 632
Mr = 293.39	Dx = 1.169 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10757 reflections
a = 5.7534 (4) Å	θ = 1.7–28.0°
b = 16.1336 (8) Å	µ = 0.07 mm−1
c = 18.1980 (13) Å	T = 296 K
β = 99.371 (6)°	Prism, colourless
V = 1666.65 (19) Å3	0.72 × 0.56 × 0.27 mm
Z = 4

Stoe IPDS 2 diffractometer	3449 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
rotation method scans	θmax = 26.5°, θmin = 1.7°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −7→7
Tmin = 0.965, Tmax = 0.985	k = −20→20
10757 measured reflections	l = −22→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0722P)2] where P = (Fo2 + 2Fc2)/3
3449 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.13 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	0.4026 (3)	0.45073 (9)	0.32943 (9)	0.0508 (4)
H1	0.5213	0.4211	0.3065	0.061*
C2	0.1676 (3)	0.41004 (10)	0.30531 (10)	0.0545 (4)
C3	0.1590 (3)	0.31909 (11)	0.28983 (11)	0.0680 (5)
H3A	0.1590	0.3111	0.2370	0.082*
H3B	0.0108	0.2978	0.3008	0.082*
C4	0.3563 (4)	0.26786 (11)	0.33231 (12)	0.0750 (6)
H4A	0.3205	0.2097	0.3229	0.090*
H4B	0.5002	0.2801	0.3131	0.090*
C5	0.3998 (5)	0.28183 (13)	0.41489 (13)	0.0919 (7)
H5A	0.2488	0.2880	0.4315	0.110*
H5B	0.4747	0.2328	0.4388	0.110*
C6	0.5488 (5)	0.35543 (15)	0.44101 (12)	0.0922 (7)
H6A	0.5733	0.3557	0.4950	0.111*
H6B	0.7017	0.3476	0.4261	0.111*
C7	0.4594 (4)	0.43901 (13)	0.41458 (11)	0.0786 (6)
H7A	0.5761	0.4800	0.4346	0.094*
H7B	0.3177	0.4505	0.4353	0.094*
C8	0.4030 (3)	0.54291 (9)	0.30610 (10)	0.0533 (4)
H8	0.2812	0.5716	0.3283	0.064*
C9	0.5035 (3)	0.52774 (10)	0.17700 (11)	0.0606 (5)
H9	0.6439	0.5026	0.1982	0.073*
C10	0.4556 (4)	0.53841 (12)	0.10111 (12)	0.0726 (5)
H10	0.5642	0.5210	0.0717	0.087*
C11	0.2490 (4)	0.57456 (13)	0.06854 (13)	0.0801 (6)
H11	0.2159	0.5810	0.0171	0.096*
C12	0.0910 (4)	0.60127 (14)	0.11243 (14)	0.0850 (7)
H12	−0.0489	0.6264	0.0907	0.102*
C13	0.1397 (3)	0.59089 (12)	0.18865 (12)	0.0713 (5)
H13	0.0314	0.6093	0.2178	0.086*
C14	0.3459 (3)	0.55379 (9)	0.22262 (10)	0.0530 (4)
C15	0.6636 (3)	0.65940 (9)	0.36011 (9)	0.0525 (4)
C16	0.8846 (3)	0.68313 (11)	0.39812 (10)	0.0604 (4)
H16	1.0051	0.6441	0.4065	0.073*
C17	0.9275 (4)	0.76247 (12)	0.42320 (12)	0.0706 (5)
H17	1.0764	0.7766	0.4481	0.085*
C18	0.7531 (4)	0.82152 (12)	0.41206 (12)	0.0760 (6)
H18	0.7823	0.8754	0.4293	0.091*
C19	0.5343 (4)	0.79933 (11)	0.37481 (12)	0.0688 (5)
H19	0.4152	0.8389	0.3671	0.083*
C20	0.4877 (3)	0.71963 (10)	0.34864 (10)	0.0587 (4)
H20	0.3387	0.7062	0.3233	0.070*
N1	0.6284 (3)	0.57845 (9)	0.33722 (10)	0.0661 (5)
O1	−0.0127 (2)	0.44979 (8)	0.30255 (10)	0.0854 (5)
H1A	0.751 (3)	0.5457 (11)	0.3392 (10)	0.064 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0554 (9)	0.0428 (8)	0.0545 (10)	0.0063 (7)	0.0095 (7)	−0.0041 (7)
C2	0.0518 (9)	0.0529 (9)	0.0604 (11)	0.0067 (8)	0.0142 (8)	0.0069 (8)
C3	0.0697 (11)	0.0561 (10)	0.0797 (13)	−0.0070 (9)	0.0166 (9)	−0.0084 (9)
C4	0.0957 (15)	0.0449 (9)	0.0878 (15)	0.0060 (10)	0.0253 (11)	0.0033 (9)
C5	0.132 (2)	0.0664 (13)	0.0802 (16)	0.0179 (13)	0.0271 (14)	0.0195 (11)
C6	0.1148 (18)	0.0980 (17)	0.0584 (13)	0.0108 (15)	−0.0023 (12)	0.0184 (11)
C7	0.1024 (16)	0.0695 (12)	0.0605 (12)	0.0015 (11)	0.0029 (11)	−0.0085 (10)
C8	0.0482 (9)	0.0410 (8)	0.0709 (11)	0.0037 (7)	0.0104 (8)	−0.0043 (7)
C9	0.0577 (10)	0.0510 (9)	0.0719 (13)	0.0038 (8)	0.0067 (9)	−0.0009 (8)
C10	0.0826 (14)	0.0633 (12)	0.0738 (14)	0.0020 (10)	0.0182 (11)	−0.0008 (9)
C11	0.0962 (16)	0.0693 (12)	0.0719 (13)	0.0007 (12)	0.0054 (12)	0.0129 (10)
C12	0.0760 (14)	0.0830 (14)	0.0903 (17)	0.0155 (11)	−0.0031 (12)	0.0220 (12)
C13	0.0606 (11)	0.0674 (11)	0.0857 (15)	0.0125 (9)	0.0110 (10)	0.0134 (10)
C14	0.0509 (9)	0.0348 (7)	0.0730 (12)	−0.0021 (7)	0.0092 (8)	0.0022 (7)
C15	0.0585 (10)	0.0456 (8)	0.0551 (10)	−0.0011 (7)	0.0142 (7)	−0.0021 (7)
C16	0.0588 (10)	0.0578 (10)	0.0639 (11)	0.0009 (8)	0.0076 (8)	−0.0071 (8)
C17	0.0700 (12)	0.0648 (11)	0.0757 (13)	−0.0106 (10)	0.0076 (10)	−0.0152 (9)
C18	0.0901 (14)	0.0522 (10)	0.0873 (15)	−0.0114 (10)	0.0198 (11)	−0.0138 (10)
C19	0.0754 (12)	0.0462 (9)	0.0876 (14)	0.0064 (9)	0.0215 (10)	0.0000 (9)
C20	0.0591 (10)	0.0469 (9)	0.0707 (12)	0.0001 (8)	0.0122 (8)	0.0007 (8)
N1	0.0520 (9)	0.0463 (8)	0.0961 (13)	0.0057 (7)	0.0010 (8)	−0.0161 (7)
O1	0.0558 (8)	0.0696 (9)	0.1328 (14)	0.0105 (7)	0.0216 (8)	0.0106 (8)

C1—C2	1.502 (2)	C9—C14	1.390 (2)
C1—C7	1.542 (2)	C9—H9	0.9300
C1—C8	1.547 (2)	C10—C11	1.369 (3)
C1—H1	0.9800	C10—H10	0.9300
C2—O1	1.214 (2)	C11—C12	1.373 (3)
C2—C3	1.493 (2)	C11—H11	0.9300
C3—C4	1.511 (3)	C12—C13	1.380 (3)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.382 (2)
C4—C5	1.500 (3)	C13—H13	0.9300
C4—H4A	0.9700	C15—N1	1.376 (2)
C4—H4B	0.9700	C15—C20	1.394 (2)
C5—C6	1.496 (3)	C15—C16	1.399 (2)
C5—H5A	0.9700	C16—C17	1.368 (2)
C5—H5B	0.9700	C16—H16	0.9300
C6—C7	1.495 (3)	C17—C18	1.375 (3)
C6—H6A	0.9700	C17—H17	0.9300
C6—H6B	0.9700	C18—C19	1.376 (3)
C7—H7A	0.9700	C18—H18	0.9300
C7—H7B	0.9700	C19—C20	1.382 (2)
C8—N1	1.446 (2)	C19—H19	0.9300
C8—C14	1.511 (2)	C20—H20	0.9300
C8—H8	0.9800	N1—H1A	0.879 (19)
C9—C10	1.374 (3)
C2—C1—C7	105.86 (14)	N1—C8—H8	107.9
C2—C1—C8	112.43 (13)	C14—C8—H8	107.9
C7—C1—C8	112.58 (14)	C1—C8—H8	107.9
C2—C1—H1	108.6	C10—C9—C14	121.25 (17)
C7—C1—H1	108.6	C10—C9—H9	119.4
C8—C1—H1	108.6	C14—C9—H9	119.4
O1—C2—C3	120.63 (16)	C11—C10—C9	120.4 (2)
O1—C2—C1	120.23 (15)	C11—C10—H10	119.8
C3—C2—C1	119.02 (14)	C9—C10—H10	119.8
C2—C3—C4	116.21 (16)	C10—C11—C12	119.5 (2)
C2—C3—H3A	108.2	C10—C11—H11	120.3
C4—C3—H3A	108.2	C12—C11—H11	120.3
C2—C3—H3B	108.2	C11—C12—C13	120.1 (2)
C4—C3—H3B	108.2	C11—C12—H12	120.0
H3A—C3—H3B	107.4	C13—C12—H12	120.0
C5—C4—C3	114.78 (17)	C12—C13—C14	121.4 (2)
C5—C4—H4A	108.6	C12—C13—H13	119.3
C3—C4—H4A	108.6	C14—C13—H13	119.3
C5—C4—H4B	108.6	C13—C14—C9	117.37 (18)
C3—C4—H4B	108.6	C13—C14—C8	122.03 (16)
H4A—C4—H4B	107.5	C9—C14—C8	120.59 (15)
C6—C5—C4	115.53 (18)	N1—C15—C20	123.29 (16)
C6—C5—H5A	108.4	N1—C15—C16	119.13 (15)
C4—C5—H5A	108.4	C20—C15—C16	117.57 (15)
C6—C5—H5B	108.4	C17—C16—C15	121.42 (17)
C4—C5—H5B	108.4	C17—C16—H16	119.3
H5A—C5—H5B	107.5	C15—C16—H16	119.3
C7—C6—C5	117.68 (19)	C16—C17—C18	120.77 (18)
C7—C6—H6A	107.9	C16—C17—H17	119.6
C5—C6—H6A	107.9	C18—C17—H17	119.6
C7—C6—H6B	107.9	C17—C18—C19	118.66 (17)
C5—C6—H6B	107.9	C17—C18—H18	120.7
H6A—C6—H6B	107.2	C19—C18—H18	120.7
C6—C7—C1	116.06 (17)	C18—C19—C20	121.50 (18)
C6—C7—H7A	108.3	C18—C19—H19	119.3
C1—C7—H7A	108.3	C20—C19—H19	119.3
C6—C7—H7B	108.3	C19—C20—C15	120.08 (17)
C1—C7—H7B	108.3	C19—C20—H20	120.0
H7A—C7—H7B	107.4	C15—C20—H20	120.0
N1—C8—C14	112.45 (14)	C15—N1—C8	124.99 (15)
N1—C8—C1	108.37 (13)	C15—N1—H1A	118.8 (12)
C14—C8—C1	112.20 (13)	C8—N1—H1A	116.2 (11)
C7—C1—C2—O1	90.59 (19)	C12—C13—C14—C9	0.4 (3)
C8—C1—C2—O1	−32.7 (2)	C12—C13—C14—C8	179.25 (17)
C7—C1—C2—C3	−85.34 (18)	C10—C9—C14—C13	−0.1 (2)
C8—C1—C2—C3	151.35 (16)	C10—C9—C14—C8	−178.96 (15)
O1—C2—C3—C4	−147.48 (19)	N1—C8—C14—C13	−125.11 (17)
C1—C2—C3—C4	28.4 (2)	C1—C8—C14—C13	112.42 (17)
C2—C3—C4—C5	50.6 (2)	N1—C8—C14—C9	53.71 (18)
C3—C4—C5—C6	−82.4 (3)	C1—C8—C14—C9	−68.77 (18)
C4—C5—C6—C7	61.6 (3)	N1—C15—C16—C17	−178.84 (17)
C5—C6—C7—C1	−56.2 (3)	C20—C15—C16—C17	0.0 (3)
C2—C1—C7—C6	78.4 (2)	C15—C16—C17—C18	0.3 (3)
C8—C1—C7—C6	−158.42 (19)	C16—C17—C18—C19	−0.3 (3)
C2—C1—C8—N1	175.01 (14)	C17—C18—C19—C20	−0.1 (3)
C7—C1—C8—N1	55.55 (19)	C18—C19—C20—C15	0.4 (3)
C2—C1—C8—C14	−60.23 (18)	N1—C15—C20—C19	178.42 (18)
C7—C1—C8—C14	−179.69 (15)	C16—C15—C20—C19	−0.4 (3)
C14—C9—C10—C11	−0.6 (3)	C20—C15—N1—C8	−7.0 (3)
C9—C10—C11—C12	1.0 (3)	C16—C15—N1—C8	171.72 (16)
C10—C11—C12—C13	−0.7 (3)	C14—C8—N1—C15	87.9 (2)
C11—C12—C13—C14	0.0 (3)	C1—C8—N1—C15	−147.48 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.879 (19)	2.23 (2)	3.065 (2)	158.4 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.879 (19)	2.23 (2)	3.065 (2)	158.4 (16)

Symmetry code: (i) .