N-[2-(2-Methoxyphenyl)benzylidene]-tert-butyl-amine N-oxide.

In the mol-ecule of the title compound, C(18)H(21)NO(2), the two benzene rings are oriented at a dihedral angle of 58.19 (3)°. Intra-molecular C-H⋯O hydrogen bonds result in the formation of one six- and one five-membered ring, which adopt twist and envelope conformations, respectively. In the crystal structure, C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Hamburger & McCay (1989 ▶); Jotti et al. (1992 ▶); Murphy et al. (2003 ▶); Green et al. (2003 ▶); Durand et al. (2007 ▶); Hay et al. (2005 ▶). For related literature, see: Fevig et al. (1996 ▶).

Experimental

Crystal data

C18H21NO2

M = 283.37

Monoclinic,

a = 10.2526 (15) Å

b = 8.5576 (13) Å

c = 10.3333 (16) Å

β = 115.742 (3)°

V = 816.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 (1) K

0.30 × 0.28 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.968, T max = 0.993

7869 measured reflections

1981 independent reflections

967 reflections with F 2 > 2σ(F 2)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.058

S = 1.00

1981 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶) and Larson (1970 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014529/hk2462sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014529/hk2462Isup2.hkl

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

C18H21NO2	F000 = 304.00
Mr = 283.37	Dx = 1.152 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 4871 reflections
a = 10.2526 (15) Å	θ = 3.2–27.4º
b = 8.5576 (13) Å	µ = 0.08 mm−1
c = 10.3333 (16) Å	T = 296 (1) K
β = 115.742 (3)º	Platelet, colorless
V = 816.6 (2) Å3	0.30 × 0.28 × 0.09 mm
Z = 2

Rigaku R-AXIS RAPID-S diffractometer	967 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.035
ω scans	θmax = 27.4º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.968, Tmax = 0.993	k = −11→10
7869 measured reflections	l = −13→13
1981 independent reflections

Refinement on F2	w = 1/[1.0600σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.034	(Δ/σ)max < 0.001
wR(F2) = 0.058	Δρmax = 0.23 e Å−3
S = 1.00	Δρmin = −0.21 e Å−3
1981 reflections	Extinction correction: Larson (1970)
191 parameters	Extinction coefficient: 287 (12)
H-atom parameters constrained

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	0.9021 (2)	0.3664 (2)	0.8067 (2)	0.1211 (8)
O2	0.89199 (16)	0.2119 (2)	0.40803 (18)	0.0749 (6)
N1	0.8516 (2)	0.2377 (2)	0.7378 (2)	0.0699 (7)
C1	0.7579 (2)	0.2359 (3)	0.6043 (2)	0.0539 (7)
C2	0.6914 (2)	0.3714 (3)	0.5161 (2)	0.0519 (7)
C3	0.6741 (2)	0.5115 (3)	0.5752 (2)	0.0657 (9)
C4	0.6018 (2)	0.6370 (3)	0.4891 (3)	0.0749 (9)
C5	0.5479 (2)	0.6233 (3)	0.3431 (3)	0.0794 (10)
C6	0.5634 (2)	0.4858 (3)	0.2821 (2)	0.0706 (9)
C7	0.6339 (2)	0.3570 (3)	0.3658 (2)	0.0552 (8)
C8	0.6389 (2)	0.2103 (3)	0.2930 (2)	0.0569 (8)
C9	0.5111 (2)	0.1408 (3)	0.1954 (2)	0.0729 (9)
C10	0.5107 (3)	0.0054 (4)	0.1245 (2)	0.0890 (11)
C11	0.6400 (3)	−0.0637 (3)	0.1491 (2)	0.0910 (11)
C12	0.7694 (3)	0.0020 (3)	0.2437 (2)	0.0775 (10)
C13	0.7690 (2)	0.1373 (3)	0.3151 (2)	0.0644 (9)
C14	1.0274 (2)	0.1362 (3)	0.4454 (3)	0.0978 (11)
C15	0.9129 (2)	0.0920 (3)	0.8265 (2)	0.0704 (9)
C16	0.8509 (3)	−0.0534 (3)	0.7407 (3)	0.1022 (12)
C17	1.0746 (2)	0.0986 (4)	0.8838 (3)	0.1160 (12)
C18	0.8694 (2)	0.1013 (4)	0.9492 (2)	0.1048 (11)
H1	0.7307	0.1385	0.5610	0.065*
H3	0.7118	0.5211	0.6745	0.079*
H4	0.5900	0.7294	0.5302	0.090*
H5	0.5004	0.7074	0.2847	0.095*
H6	0.5260	0.4787	0.1826	0.085*
H9	0.4232	0.1878	0.1778	0.087*
H10	0.4238	−0.0390	0.0605	0.107*
H11	0.6405	−0.1558	0.1016	0.109*
H12	0.8566	−0.0452	0.2591	0.093*
H141	1.0270	0.0361	0.4873	0.117*
H142	1.0425	0.1222	0.3608	0.117*
H143	1.1040	0.1992	0.5135	0.117*
H161	0.8724	−0.0552	0.6590	0.123*
H162	0.7479	−0.0546	0.7085	0.123*
H163	0.8929	−0.1435	0.7995	0.123*
H171	1.1086	0.1991	0.9263	0.139*
H172	1.1173	0.0187	0.9550	0.139*
H173	1.1015	0.0822	0.8066	0.139*
H181	0.8892	0.0033	0.9993	0.126*
H182	0.7678	0.1240	0.9117	0.126*
H183	0.9237	0.1827	1.0144	0.126*

	U11	U22	U33	U12	U13	U23
O1	0.1395 (18)	0.0722 (15)	0.0812 (15)	−0.0167 (15)	−0.0179 (12)	−0.0059 (13)
O2	0.0562 (9)	0.0805 (13)	0.0934 (13)	0.0110 (10)	0.0374 (8)	−0.0032 (12)
N1	0.0728 (13)	0.0637 (16)	0.0555 (14)	−0.0094 (14)	0.0113 (11)	−0.0029 (14)
C1	0.0509 (11)	0.0599 (18)	0.0493 (15)	−0.0037 (15)	0.0203 (11)	−0.0017 (15)
C2	0.0405 (12)	0.0608 (18)	0.0561 (16)	−0.0024 (12)	0.0227 (11)	−0.0011 (15)
C3	0.0477 (14)	0.078 (2)	0.0703 (19)	−0.0052 (14)	0.0250 (13)	−0.0124 (18)
C4	0.0504 (14)	0.068 (2)	0.103 (2)	0.0064 (15)	0.0308 (14)	−0.0027 (19)
C5	0.0627 (16)	0.076 (2)	0.097 (2)	0.0188 (17)	0.0328 (16)	0.021 (2)
C6	0.0618 (16)	0.082 (2)	0.069 (2)	0.0091 (15)	0.0299 (14)	0.0130 (19)
C7	0.0431 (13)	0.0695 (19)	0.0572 (17)	0.0068 (14)	0.0257 (11)	0.0083 (17)
C8	0.0621 (14)	0.0682 (19)	0.0450 (14)	0.0043 (16)	0.0274 (12)	0.0012 (15)
C9	0.0699 (17)	0.094 (2)	0.0497 (16)	0.0017 (16)	0.0212 (13)	−0.0003 (17)
C10	0.102 (2)	0.103 (2)	0.0586 (19)	−0.015 (2)	0.0314 (17)	−0.012 (2)
C11	0.126 (2)	0.086 (2)	0.067 (2)	−0.004 (2)	0.0474 (19)	−0.0130 (18)
C12	0.097 (2)	0.078 (2)	0.069 (2)	0.0104 (17)	0.0472 (17)	0.0009 (18)
C13	0.0699 (16)	0.075 (2)	0.0579 (17)	0.0022 (16)	0.0366 (13)	0.0008 (16)
C14	0.0666 (15)	0.105 (2)	0.130 (2)	0.0198 (18)	0.0496 (15)	0.008 (2)
C15	0.0706 (17)	0.069 (2)	0.0573 (18)	0.0000 (17)	0.0146 (13)	0.0103 (17)
C16	0.129 (2)	0.066 (2)	0.087 (2)	0.008 (2)	0.0230 (19)	0.0098 (19)
C17	0.0771 (17)	0.121 (2)	0.124 (2)	0.003 (2)	0.0196 (16)	0.033 (2)
C18	0.113 (2)	0.120 (2)	0.0668 (19)	0.010 (2)	0.0254 (17)	0.025 (2)

O1—N1	1.291 (3)	C1—H1	0.930
O2—C13	1.366 (2)	C3—H3	0.930
O2—C14	1.425 (3)	C4—H4	0.930
N1—C1	1.293 (2)	C5—H5	0.930
N1—C15	1.514 (3)	C6—H6	0.930
C1—C2	1.450 (3)	C9—H9	0.930
C2—C3	1.391 (4)	C10—H10	0.930
C2—C7	1.407 (3)	C11—H11	0.930
C3—C4	1.386 (3)	C12—H12	0.930
C4—C5	1.368 (4)	C14—H141	0.960
C5—C6	1.376 (4)	C14—H142	0.960
C6—C7	1.394 (3)	C14—H143	0.960
C7—C8	1.476 (3)	C16—H161	0.960
C8—C9	1.393 (3)	C16—H162	0.960
C8—C13	1.399 (3)	C16—H163	0.960
C9—C10	1.370 (4)	C17—H171	0.960
C10—C11	1.371 (5)	C17—H172	0.960
C11—C12	1.381 (3)	C17—H173	0.960
C12—C13	1.373 (4)	C18—H181	0.960
C15—C16	1.499 (3)	C18—H182	0.960
C15—C17	1.500 (3)	C18—H183	0.960
C15—C18	1.518 (4)
C13—O2—C14	118.1 (2)	C4—C5—H5	119.8
O1—N1—C1	122.2 (2)	C6—C5—H5	119.8
O1—N1—C15	114.02 (18)	C5—C6—H6	119.2
C1—N1—C15	123.8 (2)	C7—C6—H6	119.2
N1—C1—C2	126.1 (2)	C8—C9—H9	118.9
C1—C2—C3	121.9 (2)	C10—C9—H9	118.9
C1—C2—C7	118.8 (2)	C9—C10—H10	120.4
C3—C2—C7	119.2 (2)	C11—C10—H10	120.4
C2—C3—C4	121.4 (2)	C10—C11—H11	119.7
C3—C4—C5	119.2 (2)	C12—C11—H11	119.7
C4—C5—C6	120.5 (2)	C11—C12—H12	120.1
C5—C6—C7	121.6 (2)	C13—C12—H12	120.1
C2—C7—C6	118.1 (2)	O2—C14—H141	109.5
C2—C7—C8	123.1 (2)	O2—C14—H142	109.5
C6—C7—C8	118.7 (2)	O2—C14—H143	109.5
C7—C8—C9	120.2 (2)	H141—C14—H142	109.5
C7—C8—C13	122.56 (19)	H141—C14—H143	109.5
C9—C8—C13	117.3 (2)	H142—C14—H143	109.5
C8—C9—C10	122.1 (2)	C15—C16—H161	109.5
C9—C10—C11	119.2 (2)	C15—C16—H162	109.5
C10—C11—C12	120.7 (3)	C15—C16—H163	109.5
C11—C12—C13	119.9 (3)	H161—C16—H162	109.5
O2—C13—C8	115.4 (2)	H161—C16—H163	109.5
O2—C13—C12	123.7 (2)	H162—C16—H163	109.5
C8—C13—C12	120.9 (2)	C15—C17—H171	109.5
N1—C15—C16	111.56 (19)	C15—C17—H172	109.5
N1—C15—C17	107.7 (2)	C15—C17—H173	109.5
N1—C15—C18	105.5 (2)	H171—C17—H172	109.5
C16—C15—C17	112.1 (2)	H171—C17—H173	109.5
C16—C15—C18	109.6 (2)	H172—C17—H173	109.5
C17—C15—C18	110.1 (2)	C15—C18—H181	109.5
N1—C1—H1	116.9	C15—C18—H182	109.5
C2—C1—H1	116.9	C15—C18—H183	109.5
C2—C3—H3	119.3	H181—C18—H182	109.5
C4—C3—H3	119.3	H181—C18—H183	109.5
C3—C4—H4	120.4	H182—C18—H183	109.5
C5—C4—H4	120.4
C14—O2—C13—C8	174.2 (2)	C3—C4—C5—C6	0.9 (4)
C14—O2—C13—C12	−7.4 (4)	C4—C5—C6—C7	−0.1 (3)
O1—N1—C1—C2	−3.3 (4)	C5—C6—C7—C2	−0.9 (4)
O1—N1—C15—C16	−179.7 (2)	C5—C6—C7—C8	176.3 (2)
O1—N1—C15—C17	−56.2 (3)	C2—C7—C8—C9	121.0 (2)
O1—N1—C15—C18	61.4 (2)	C2—C7—C8—C13	−60.5 (4)
C1—N1—C15—C16	−0.3 (4)	C6—C7—C8—C9	−56.0 (3)
C1—N1—C15—C17	123.2 (2)	C6—C7—C8—C13	122.5 (2)
C1—N1—C15—C18	−119.2 (2)	C7—C8—C9—C10	179.5 (2)
C15—N1—C1—C2	177.4 (2)	C7—C8—C13—O2	−0.6 (4)
N1—C1—C2—C3	−26.8 (4)	C7—C8—C13—C12	−179.0 (2)
N1—C1—C2—C7	157.7 (2)	C9—C8—C13—O2	178.0 (2)
C1—C2—C3—C4	−175.7 (2)	C9—C8—C13—C12	−0.5 (4)
C1—C2—C7—C6	176.6 (2)	C13—C8—C9—C10	0.9 (4)
C1—C2—C7—C8	−0.5 (3)	C8—C9—C10—C11	−0.5 (5)
C3—C2—C7—C6	1.0 (3)	C9—C10—C11—C12	−0.2 (4)
C3—C2—C7—C8	−176.1 (2)	C10—C11—C12—C13	0.6 (5)
C7—C2—C3—C4	−0.2 (3)	C11—C12—C13—O2	−178.5 (2)
C2—C3—C4—C5	−0.8 (4)	C11—C12—C13—C8	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.26	2.806 (3)	117
C17—H171···O1	0.96	2.41	2.791 (3)	104
C18—H181···O1i	0.96	2.50	3.280 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.93	2.26	2.806 (3)	117
C17—H171⋯O1	0.96	2.41	2.791 (3)	104
C18—H181⋯O1i	0.96	2.50	3.280 (3)	139

Symmetry code: (i) .