(Z)-1-(3-Mesityl-3-methyl-cyclo-but-yl)-2-(morpholin-4-yl)ethanone oxime.

In the title compound, C(20)H(30)N(2)O(2), the cyclo-butane ring is puckered, with a dihedral angle of 19.60 (13)° between the two planes. In the crystal, the mol-ecules are linked by inter-molecular O-H⋯N and weak C-H⋯O hydrogen bonds, as well as a C-H⋯π hydrogen-bonding association.

Related literature

For applications of related compounds, see: Dehmlow & Schmidt (1990 ▶); Coghi et al. (1976 ▶); Mixich & Thiele (1979 ▶); Migrdichian (1957 ▶); Mathison et al. (1989 ▶); Polak (1982 ▶); Balsamo et al., 1990 ▶; Holan et al. (1984 ▶); Marsman et al. (1999 ▶); Forman (1964 ▶); Bertolasi et al. (1982 ▶); Gilli et al. (1983 ▶); Hökelek et al. (2001 ▶). For related structures, see: Özdemir et al. (2004 ▶); Dinçer et al. (2004 ▶). For the puckering of the cyclobutane ring, see: Swenson et al. (1997 ▶).

Experimental

Crystal data

C20H30N2O2

M = 330.46

Monoclinic,

a = 13.0273 (4) Å

b = 10.2337 (2) Å

c = 18.1262 (6) Å

β = 126.574 (2)°

V = 1940.69 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.60 × 0.55 × 0.48 mm

Data collection

Stoe IPDS II CCD area-detector diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.964, T max = 0.977

28812 measured reflections

4031 independent reflections

3110 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.171

S = 1.09

4031 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009408/zs2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009408/zs2100Isup2.hkl

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

C20H30N2O2	F(000) = 720
Mr = 330.46	Dx = 1.131 Mg m−3
Monoclinic, P21/c	Melting point: 428 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.0273 (4) Å	Cell parameters from 29343 reflections
b = 10.2337 (2) Å	θ = 1.4–28.0°
c = 18.1262 (6) Å	µ = 0.07 mm−1
β = 126.574 (2)°	T = 296 K
V = 1940.69 (10) Å3	Prism, colourless
Z = 4	0.60 × 0.55 × 0.48 mm

Stoe IPDS II CCD area-detector diffractometer	4031 independent reflections
Radiation source: fine-focus sealed tube	3110 reflections with I > 2σ(I)
graphite	Rint = 0.058
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
rotation method scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.964, Tmax = 0.977	l = −22→22
28812 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.097P)2 + 0.1596P] where P = (Fo2 + 2Fc2)/3
4031 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 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	0.36380 (14)	−0.05777 (14)	0.74190 (10)	0.0528 (4)
C2	0.46281 (15)	−0.05329 (16)	0.83667 (11)	0.0601 (4)
C3	0.46390 (18)	−0.1424 (2)	0.89474 (12)	0.0715 (5)
H3	0.5287	−0.1366	0.9575	0.086*
C4	0.3733 (2)	−0.2391 (2)	0.86371 (15)	0.0758 (5)
C5	0.28345 (19)	−0.24910 (18)	0.77046 (15)	0.0752 (5)
H5	0.2242	−0.3167	0.7476	0.090*
C6	0.27696 (16)	−0.16278 (16)	0.70854 (12)	0.0625 (4)
C7	0.1786 (2)	−0.1905 (2)	0.60720 (14)	0.0886 (6)
H7A	0.1295	−0.2660	0.5997	0.133*
H7B	0.2212	−0.2066	0.5794	0.133*
H7C	0.1229	−0.1166	0.5782	0.133*
C8	0.57461 (17)	0.0403 (2)	0.87941 (14)	0.0814 (6)
H8A	0.5632	0.0968	0.8328	0.122*
H8B	0.6524	−0.0084	0.9071	0.122*
H8C	0.5790	0.0918	0.9255	0.122*
C9	0.3761 (3)	−0.3317 (3)	0.9297 (2)	0.1137 (9)
H9A	0.4450	−0.3083	0.9916	0.171*
H9B	0.3885	−0.4194	0.9175	0.171*
H9C	0.2966	−0.3265	0.9219	0.171*
C10	0.4242 (2)	0.0076 (2)	0.63806 (16)	0.0834 (6)
H10A	0.4154	0.0753	0.5979	0.125*
H10B	0.3894	−0.0724	0.6042	0.125*
H10C	0.5131	−0.0045	0.6874	0.125*
C11	0.35215 (14)	0.04679 (15)	0.67740 (11)	0.0556 (4)
C12	0.38414 (15)	0.18873 (15)	0.71533 (12)	0.0603 (4)
H12A	0.3857	0.2003	0.7691	0.072*
H12B	0.4617	0.2227	0.7263	0.072*
C13	0.26170 (15)	0.24003 (16)	0.62660 (12)	0.0612 (4)
H13	0.2804	0.2744	0.5853	0.073*
C14	0.21439 (16)	0.09740 (16)	0.60114 (11)	0.0622 (4)
H14A	0.1840	0.0734	0.5394	0.075*
H14B	0.1520	0.0746	0.6119	0.075*
C15	0.18063 (15)	0.33490 (15)	0.63429 (12)	0.0597 (4)
C16	0.18719 (17)	0.34202 (17)	0.71954 (13)	0.0659 (4)
H16A	0.2731	0.3658	0.7713	0.079*
H16B	0.1291	0.4090	0.7123	0.079*
C17	0.01643 (17)	0.1917 (2)	0.67605 (14)	0.0768 (5)
H17A	−0.0136	0.1987	0.6127	0.092*
H17B	−0.0288	0.2556	0.6863	0.092*
C18	−0.0090 (2)	0.0568 (3)	0.69414 (19)	0.0989 (7)
H18A	−0.1000	0.0394	0.6532	0.119*
H18B	0.0338	−0.0066	0.6813	0.119*
C19	0.1671 (3)	0.0674 (3)	0.84584 (18)	0.1042 (8)
H19A	0.2119	0.0042	0.8346	0.125*
H19B	0.1968	0.0574	0.9089	0.125*
C20	0.1967 (2)	0.2022 (2)	0.83206 (14)	0.0853 (6)
H20A	0.1544	0.2658	0.8451	0.102*
H20B	0.2881	0.2175	0.8738	0.102*
N1	0.09976 (13)	0.41245 (15)	0.57100 (11)	0.0688 (4)
N2	0.15302 (12)	0.21666 (14)	0.73755 (9)	0.0607 (4)
O1	0.09479 (13)	0.40408 (15)	0.49164 (10)	0.0860 (5)
H1	0.0415	0.4558	0.4531	0.129*
O2	0.03433 (18)	0.0426 (2)	0.78590 (14)	0.1121 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0502 (7)	0.0468 (8)	0.0587 (8)	0.0063 (6)	0.0309 (7)	0.0032 (6)
C2	0.0531 (8)	0.0541 (9)	0.0625 (9)	0.0078 (6)	0.0288 (7)	0.0039 (7)
C3	0.0706 (10)	0.0733 (11)	0.0618 (10)	0.0145 (9)	0.0347 (8)	0.0132 (8)
C4	0.0818 (12)	0.0698 (11)	0.0875 (13)	0.0176 (9)	0.0567 (11)	0.0240 (10)
C5	0.0735 (11)	0.0534 (9)	0.1002 (14)	−0.0039 (8)	0.0526 (11)	0.0056 (9)
C6	0.0595 (9)	0.0489 (8)	0.0701 (10)	−0.0001 (7)	0.0337 (8)	−0.0010 (7)
C7	0.0829 (13)	0.0665 (11)	0.0782 (13)	−0.0119 (9)	0.0273 (10)	−0.0135 (9)
C8	0.0540 (9)	0.0729 (12)	0.0757 (12)	0.0005 (8)	0.0161 (9)	0.0020 (9)
C9	0.132 (2)	0.1057 (19)	0.130 (2)	0.0176 (15)	0.0929 (19)	0.0460 (16)
C10	0.0956 (14)	0.0795 (12)	0.1036 (15)	0.0194 (11)	0.0748 (13)	0.0129 (11)
C11	0.0547 (8)	0.0525 (8)	0.0620 (9)	0.0068 (6)	0.0360 (7)	0.0056 (7)
C12	0.0513 (8)	0.0492 (8)	0.0768 (10)	0.0033 (6)	0.0362 (8)	0.0077 (7)
C13	0.0623 (9)	0.0582 (9)	0.0717 (10)	0.0118 (7)	0.0447 (8)	0.0181 (7)
C14	0.0623 (9)	0.0614 (9)	0.0546 (9)	0.0093 (7)	0.0303 (7)	0.0056 (7)
C15	0.0561 (8)	0.0487 (8)	0.0770 (10)	0.0061 (6)	0.0411 (8)	0.0153 (7)
C16	0.0649 (9)	0.0578 (9)	0.0783 (11)	0.0075 (7)	0.0443 (9)	0.0049 (8)
C17	0.0589 (10)	0.0881 (13)	0.0795 (12)	0.0028 (9)	0.0392 (9)	0.0151 (10)
C18	0.0821 (13)	0.1011 (17)	0.1184 (19)	−0.0112 (12)	0.0623 (14)	0.0161 (14)
C19	0.1032 (17)	0.135 (2)	0.0954 (16)	0.0212 (15)	0.0707 (15)	0.0459 (15)
C20	0.0821 (12)	0.1126 (17)	0.0656 (11)	0.0095 (11)	0.0464 (10)	0.0115 (11)
N1	0.0620 (8)	0.0629 (8)	0.0853 (10)	0.0120 (6)	0.0460 (8)	0.0260 (7)
N2	0.0563 (7)	0.0677 (8)	0.0599 (8)	0.0052 (6)	0.0357 (6)	0.0100 (6)
O1	0.0755 (8)	0.1020 (11)	0.0870 (9)	0.0268 (7)	0.0519 (7)	0.0429 (8)
O2	0.1121 (13)	0.1290 (15)	0.1348 (15)	0.0072 (10)	0.0949 (12)	0.0415 (11)

C1—C2	1.406 (2)	C12—H12A	0.9700
C1—C6	1.409 (2)	C12—H12B	0.9700
C1—C11	1.524 (2)	C13—C15	1.501 (2)
C2—C3	1.386 (3)	C13—C14	1.544 (2)
C2—C8	1.515 (3)	C13—H13	0.9800
C3—C4	1.378 (3)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.371 (3)	C15—N1	1.271 (2)
C4—C9	1.509 (3)	C15—C16	1.498 (3)
C5—C6	1.391 (3)	C16—N2	1.457 (2)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.514 (3)	C16—H16B	0.9700
C7—H7A	0.9600	C17—N2	1.453 (2)
C7—H7B	0.9600	C17—C18	1.500 (3)
C7—H7C	0.9600	C17—H17A	0.9700
C8—H8A	0.9600	C17—H17B	0.9700
C8—H8B	0.9600	C18—O2	1.410 (3)
C8—H8C	0.9600	C18—H18A	0.9700
C9—H9A	0.9600	C18—H18B	0.9700
C9—H9B	0.9600	C19—O2	1.414 (3)
C9—H9C	0.9600	C19—C20	1.493 (4)
C10—C11	1.533 (2)	C19—H19A	0.9700
C10—H10A	0.9600	C19—H19B	0.9700
C10—H10B	0.9600	C20—N2	1.456 (2)
C10—H10C	0.9600	C20—H20A	0.9700
C11—C12	1.554 (2)	C20—H20B	0.9700
C11—C14	1.563 (2)	N1—O1	1.404 (2)
C12—C13	1.533 (2)	O1—H1	0.8200
C2—C1—C6	117.83 (14)	H12A—C12—H12B	110.8
C2—C1—C11	120.93 (14)	C15—C13—C12	118.29 (15)
C6—C1—C11	121.24 (14)	C15—C13—C14	117.48 (14)
C3—C2—C1	119.55 (16)	C12—C13—C14	88.30 (12)
C3—C2—C8	117.12 (16)	C15—C13—H13	110.3
C1—C2—C8	123.24 (16)	C12—C13—H13	110.3
C4—C3—C2	122.95 (17)	C14—C13—H13	110.3
C4—C3—H3	118.5	C13—C14—C11	90.31 (12)
C2—C3—H3	118.5	C13—C14—H14A	113.6
C5—C4—C3	116.83 (17)	C11—C14—H14A	113.6
C5—C4—C9	122.0 (2)	C13—C14—H14B	113.6
C3—C4—C9	121.2 (2)	C11—C14—H14B	113.6
C4—C5—C6	122.97 (18)	H14A—C14—H14B	110.9
C4—C5—H5	118.5	N1—C15—C16	114.07 (15)
C6—C5—H5	118.5	N1—C15—C13	124.80 (17)
C5—C6—C1	119.40 (16)	C16—C15—C13	121.10 (13)
C5—C6—C7	117.43 (17)	N2—C16—C15	110.55 (14)
C1—C6—C7	123.12 (16)	N2—C16—H16A	109.5
C6—C7—H7A	109.5	C15—C16—H16A	109.5
C6—C7—H7B	109.5	N2—C16—H16B	109.5
H7A—C7—H7B	109.5	C15—C16—H16B	109.5
C6—C7—H7C	109.5	H16A—C16—H16B	108.1
H7A—C7—H7C	109.5	N2—C17—C18	108.85 (16)
H7B—C7—H7C	109.5	N2—C17—H17A	109.9
C2—C8—H8A	109.5	C18—C17—H17A	109.9
C2—C8—H8B	109.5	N2—C17—H17B	109.9
H8A—C8—H8B	109.5	C18—C17—H17B	109.9
C2—C8—H8C	109.5	H17A—C17—H17B	108.3
H8A—C8—H8C	109.5	O2—C18—C17	111.6 (2)
H8B—C8—H8C	109.5	O2—C18—H18A	109.3
C4—C9—H9A	109.5	C17—C18—H18A	109.3
C4—C9—H9B	109.5	O2—C18—H18B	109.3
H9A—C9—H9B	109.5	C17—C18—H18B	109.3
C4—C9—H9C	109.5	H18A—C18—H18B	108.0
H9A—C9—H9C	109.5	O2—C19—C20	110.93 (19)
H9B—C9—H9C	109.5	O2—C19—H19A	109.5
C11—C10—H10A	109.5	C20—C19—H19A	109.5
C11—C10—H10B	109.5	O2—C19—H19B	109.5
H10A—C10—H10B	109.5	C20—C19—H19B	109.5
C11—C10—H10C	109.5	H19A—C19—H19B	108.0
H10A—C10—H10C	109.5	N2—C20—C19	109.40 (19)
H10B—C10—H10C	109.5	N2—C20—H20A	109.8
C1—C11—C10	111.39 (13)	C19—C20—H20A	109.8
C1—C11—C12	116.03 (14)	N2—C20—H20B	109.8
C10—C11—C12	111.90 (15)	C19—C20—H20B	109.8
C1—C11—C14	116.62 (13)	H20A—C20—H20B	108.2
C10—C11—C14	111.97 (15)	C15—N1—O1	113.21 (15)
C12—C11—C14	86.87 (11)	C17—N2—C20	109.05 (15)
C13—C12—C11	91.08 (12)	C17—N2—C16	112.40 (13)
C13—C12—H12A	113.5	C20—N2—C16	113.32 (16)
C11—C12—H12A	113.5	N1—O1—H1	109.5
C13—C12—H12B	113.5	C18—O2—C19	109.51 (16)
C11—C12—H12B	113.5
C6—C1—C2—C3	−6.9 (2)	C11—C12—C13—C15	134.65 (15)
C11—C1—C2—C3	173.84 (15)	C11—C12—C13—C14	14.10 (13)
C6—C1—C2—C8	169.57 (16)	C15—C13—C14—C11	−135.28 (15)
C11—C1—C2—C8	−9.6 (2)	C12—C13—C14—C11	−14.01 (13)
C1—C2—C3—C4	1.8 (3)	C1—C11—C14—C13	131.49 (14)
C8—C2—C3—C4	−174.94 (18)	C10—C11—C14—C13	−98.55 (16)
C2—C3—C4—C5	3.5 (3)	C12—C11—C14—C13	13.83 (13)
C2—C3—C4—C9	−178.3 (2)	C12—C13—C15—N1	159.02 (16)
C3—C4—C5—C6	−3.6 (3)	C14—C13—C15—N1	−97.0 (2)
C9—C4—C5—C6	178.3 (2)	C12—C13—C15—C16	−22.9 (2)
C4—C5—C6—C1	−1.6 (3)	C14—C13—C15—C16	81.1 (2)
C4—C5—C6—C7	175.97 (19)	N1—C15—C16—N2	118.59 (16)
C2—C1—C6—C5	6.9 (2)	C13—C15—C16—N2	−59.7 (2)
C11—C1—C6—C5	−173.91 (15)	N2—C17—C18—O2	59.1 (2)
C2—C1—C6—C7	−170.59 (17)	O2—C19—C20—N2	−59.6 (3)
C11—C1—C6—C7	8.6 (3)	C16—C15—N1—O1	−179.84 (14)
C2—C1—C11—C10	91.37 (19)	C13—C15—N1—O1	−1.6 (2)
C6—C1—C11—C10	−87.81 (19)	C18—C17—N2—C20	−58.0 (2)
C2—C1—C11—C12	−38.2 (2)	C18—C17—N2—C16	175.45 (18)
C6—C1—C11—C12	142.60 (15)	C19—C20—N2—C17	58.7 (2)
C2—C1—C11—C14	−138.40 (15)	C19—C20—N2—C16	−175.29 (17)
C6—C1—C11—C14	42.4 (2)	C15—C16—N2—C17	−74.95 (18)
C1—C11—C12—C13	−132.15 (13)	C15—C16—N2—C20	160.85 (15)
C10—C11—C12—C13	98.51 (15)	C17—C18—O2—C19	−59.2 (3)
C14—C11—C12—C13	−13.94 (13)	C20—C19—O2—C18	59.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.11	2.7944 (19)	141
C16—H16B···O2ii	0.97	2.55	3.494 (2)	165
C19—H19B···O1iii	0.97	2.56	3.305 (3)	134
C12—H12B···Cg1iv	0.97	2.84	3.777 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.11	2.7944 (19)	141
C16—H16B⋯O2ii	0.97	2.55	3.494 (2)	165
C19—H19B⋯O1iii	0.97	2.56	3.305 (3)	134
C12—H12B⋯Cg1iv	0.97	2.84	3.777 (3)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .