2-Iodo-3-(4-meth-oxy-anilino)-5,5-dimethyl-cyclo-hex-2-en-1-one.

The cyclo-hexene ring in the title compound, C(15)H(18)INO(2), adopts a sofa conformation. The dihedral angle between the cyclo-hexene (through all ring atoms) and benzene rings is 63.3 (1)°. The mol-ecular conformation features an N-H⋯I short contact and the crystal packing features C-H⋯O hydrogen bonds.

Related literature

For the biological activity of cyclo­hex-2-enone derivatives, see: Correia et al. (2001 ▶); Rebacz et al. (2007 ▶); Stadler et al. (1994 ▶). For the use of cyclo­hex-2-enone in organic synthesis, see: Cokcer et al. (1995 ▶); Pandey et al. (2004 ▶). For pukering parameters, see: Cremer & Pople, (1975 ▶). For related structures, see: Mohan et al. (2008 ▶); North et al. (2011 ▶).

Experimental

Crystal data

C15H18INO2

M = 371.20

Orthorhombic,

a = 15.922 (5) Å

b = 10.107 (5) Å

c = 19.034 (5) Å

V = 3063 (2) Å3

Z = 8

Mo Kα radiation

μ = 2.09 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

15382 measured reflections

3785 independent reflections

2793 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.074

S = 0.93

3785 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002255/kp2383sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002255/kp2383Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002255/kp2383Isup3.cml

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

C15H18INO2	F(000) = 1472
Mr = 371.20	Dx = 1.610 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3785 reflections
a = 15.922 (5) Å	θ = 2.1–28.3°
b = 10.107 (5) Å	µ = 2.09 mm−1
c = 19.034 (5) Å	T = 298 K
V = 3063 (2) Å3	Block, colourless
Z = 8	0.20 × 0.20 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	2793 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 28.3°, θmin = 2.1°
ω and φ scans	h = −20→21
15382 measured reflections	k = −13→13
3785 independent reflections	l = −18→25

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0379P)2 + 1.6353P] where P = (Fo2 + 2Fc2)/3
3785 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.53 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
I1	0.423501 (11)	0.337299 (16)	0.478996 (11)	0.05300 (8)
O1	0.52198 (11)	0.14887 (18)	0.37743 (10)	0.0540 (5)
O2	0.07995 (12)	−0.1517 (2)	0.71999 (11)	0.0631 (6)
N1	0.30564 (14)	0.1095 (2)	0.54533 (12)	0.0460 (5)
H1	0.3092	0.1935	0.5520	0.055*
C1	0.45213 (16)	−0.0582 (3)	0.38180 (14)	0.0477 (6)
H1A	0.4938	−0.1126	0.4052	0.057*
H1B	0.4621	−0.0650	0.3317	0.057*
C2	0.46504 (15)	0.0831 (2)	0.40367 (13)	0.0401 (5)
C3	0.40963 (15)	0.1356 (2)	0.45650 (14)	0.0390 (5)
C4	0.35334 (15)	0.0597 (2)	0.49300 (12)	0.0378 (5)
C5	0.34440 (16)	−0.0847 (2)	0.47456 (12)	0.0417 (5)
H5A	0.2873	−0.1125	0.4844	0.050*
H5B	0.3816	−0.1360	0.5044	0.050*
C6	0.36464 (17)	−0.1148 (3)	0.39783 (13)	0.0456 (6)
C7	0.3655 (2)	−0.2658 (3)	0.38817 (17)	0.0698 (9)
H7A	0.3780	−0.2866	0.3401	0.105*
H7B	0.3115	−0.3012	0.4003	0.105*
H7C	0.4076	−0.3039	0.4181	0.105*
C8	0.29981 (18)	−0.0539 (3)	0.34872 (15)	0.0585 (7)
H8A	0.3142	−0.0742	0.3009	0.088*
H8B	0.2990	0.0403	0.3550	0.088*
H8C	0.2453	−0.0895	0.3592	0.088*
C9	0.24994 (15)	0.0393 (2)	0.59096 (12)	0.0381 (5)
C10	0.16832 (16)	0.0851 (2)	0.59962 (13)	0.0424 (5)
H10	0.1502	0.1594	0.5751	0.051*
C11	0.11454 (15)	0.0208 (3)	0.64420 (13)	0.0455 (6)
H11	0.0605	0.0536	0.6508	0.055*
C12	0.13951 (16)	−0.0923 (3)	0.67950 (12)	0.0437 (6)
C13	0.22144 (16)	−0.1371 (3)	0.67234 (13)	0.0437 (6)
H13	0.2393	−0.2119	0.6965	0.052*
C14	0.27628 (15)	−0.0696 (2)	0.62894 (13)	0.0432 (5)
H14	0.3317	−0.0978	0.6252	0.052*
C15	0.1004 (2)	−0.2714 (3)	0.75369 (18)	0.0698 (9)
H15A	0.0528	−0.3020	0.7801	0.105*
H15B	0.1469	−0.2573	0.7849	0.105*
H15C	0.1154	−0.3364	0.7191	0.105*

	U11	U22	U33	U12	U13	U23
I1	0.05114 (12)	0.03804 (11)	0.06982 (15)	−0.00787 (7)	0.00678 (9)	−0.00135 (8)
O1	0.0359 (9)	0.0657 (12)	0.0603 (12)	−0.0075 (8)	0.0092 (9)	0.0037 (9)
O2	0.0516 (12)	0.0801 (16)	0.0577 (12)	−0.0013 (10)	0.0190 (9)	0.0170 (10)
N1	0.0504 (12)	0.0374 (11)	0.0503 (12)	−0.0041 (9)	0.0158 (10)	−0.0014 (9)
C1	0.0425 (13)	0.0544 (15)	0.0463 (14)	0.0056 (12)	0.0054 (12)	−0.0065 (12)
C2	0.0310 (11)	0.0487 (14)	0.0406 (13)	−0.0014 (10)	−0.0019 (10)	0.0016 (11)
C3	0.0388 (12)	0.0349 (12)	0.0432 (13)	−0.0038 (9)	−0.0004 (10)	−0.0004 (10)
C4	0.0368 (12)	0.0384 (12)	0.0381 (12)	−0.0022 (10)	−0.0006 (10)	−0.0005 (10)
C5	0.0459 (14)	0.0373 (12)	0.0419 (13)	−0.0069 (10)	0.0024 (11)	0.0000 (10)
C6	0.0489 (14)	0.0450 (14)	0.0428 (14)	−0.0053 (11)	0.0023 (12)	−0.0077 (11)
C7	0.088 (2)	0.0530 (18)	0.0683 (19)	−0.0100 (17)	0.0057 (18)	−0.0191 (15)
C8	0.0502 (15)	0.075 (2)	0.0503 (16)	−0.0110 (15)	−0.0060 (13)	−0.0034 (14)
C9	0.0406 (12)	0.0369 (11)	0.0370 (12)	−0.0015 (10)	0.0040 (10)	−0.0040 (10)
C10	0.0464 (13)	0.0411 (13)	0.0398 (13)	0.0056 (11)	0.0006 (11)	0.0000 (10)
C11	0.0354 (12)	0.0572 (16)	0.0440 (13)	0.0067 (11)	0.0054 (11)	−0.0043 (12)
C12	0.0440 (13)	0.0552 (15)	0.0318 (12)	−0.0019 (11)	0.0072 (11)	−0.0021 (11)
C13	0.0458 (14)	0.0488 (14)	0.0367 (13)	0.0052 (11)	0.0041 (11)	0.0042 (10)
C14	0.0358 (12)	0.0499 (14)	0.0440 (13)	0.0078 (11)	0.0038 (11)	−0.0008 (11)
C15	0.083 (2)	0.067 (2)	0.0587 (18)	−0.0143 (18)	0.0167 (17)	0.0092 (16)

I1—C3	2.095 (3)	C7—H7A	0.9600
O1—C2	1.230 (3)	C7—H7B	0.9600
O2—C12	1.361 (3)	C7—H7C	0.9600
O2—C15	1.407 (4)	C8—H8A	0.9600
N1—C4	1.350 (3)	C8—H8B	0.9600
N1—C9	1.430 (3)	C8—H8C	0.9600
N1—H1	0.8600	C9—C14	1.382 (3)
C1—C2	1.501 (4)	C9—C10	1.389 (3)
C1—C6	1.537 (4)	C10—C11	1.369 (3)
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700	C11—C12	1.385 (4)
C2—C3	1.439 (3)	C11—H11	0.9300
C3—C4	1.369 (3)	C12—C13	1.387 (3)
C4—C5	1.508 (3)	C13—C14	1.382 (3)
C5—C6	1.526 (3)	C13—H13	0.9300
C5—H5A	0.9700	C14—H14	0.9300
C5—H5B	0.9700	C15—H15A	0.9600
C6—C8	1.523 (4)	C15—H15B	0.9600
C6—C7	1.537 (4)	C15—H15C	0.9600
C12—O2—C15	118.4 (2)	C6—C7—H7C	109.5
C4—N1—C9	127.7 (2)	H7A—C7—H7C	109.5
C4—N1—H1	116.1	H7B—C7—H7C	109.5
C9—N1—H1	116.1	C6—C8—H8A	109.5
C2—C1—C6	115.0 (2)	C6—C8—H8B	109.5
C2—C1—H1A	108.5	H8A—C8—H8B	109.5
C6—C1—H1A	108.5	C6—C8—H8C	109.5
C2—C1—H1B	108.5	H8A—C8—H8C	109.5
C6—C1—H1B	108.5	H8B—C8—H8C	109.5
H1A—C1—H1B	107.5	C14—C9—C10	119.1 (2)
O1—C2—C3	122.4 (2)	C14—C9—N1	121.7 (2)
O1—C2—C1	120.2 (2)	C10—C9—N1	119.1 (2)
C3—C2—C1	117.4 (2)	C11—C10—C9	120.0 (2)
C4—C3—C2	123.3 (2)	C11—C10—H10	120.0
C4—C3—I1	120.70 (18)	C9—C10—H10	120.0
C2—C3—I1	115.92 (17)	C10—C11—C12	120.9 (2)
N1—C4—C3	122.3 (2)	C10—C11—H11	119.6
N1—C4—C5	118.7 (2)	C12—C11—H11	119.6
C3—C4—C5	119.1 (2)	O2—C12—C11	116.0 (2)
C4—C5—C6	113.3 (2)	O2—C12—C13	124.5 (2)
C4—C5—H5A	108.9	C11—C12—C13	119.4 (2)
C6—C5—H5A	108.9	C14—C13—C12	119.5 (2)
C4—C5—H5B	108.9	C14—C13—H13	120.3
C6—C5—H5B	108.9	C12—C13—H13	120.3
H5A—C5—H5B	107.7	C9—C14—C13	120.9 (2)
C8—C6—C5	111.3 (2)	C9—C14—H14	119.5
C8—C6—C1	110.0 (2)	C13—C14—H14	119.5
C5—C6—C1	107.9 (2)	O2—C15—H15A	109.5
C8—C6—C7	109.5 (2)	O2—C15—H15B	109.5
C5—C6—C7	108.3 (2)	H15A—C15—H15B	109.5
C1—C6—C7	109.7 (2)	O2—C15—H15C	109.5
C6—C7—H7A	109.5	H15A—C15—H15C	109.5
C6—C7—H7B	109.5	H15B—C15—H15C	109.5
H7A—C7—H7B	109.5
C6—C1—C2—O1	−160.3 (2)	C2—C1—C6—C8	71.8 (3)
C6—C1—C2—C3	20.7 (3)	C2—C1—C6—C5	−49.8 (3)
O1—C2—C3—C4	−171.1 (2)	C2—C1—C6—C7	−167.7 (2)
C1—C2—C3—C4	7.9 (4)	C4—N1—C9—C14	53.2 (4)
O1—C2—C3—I1	6.0 (3)	C4—N1—C9—C10	−129.6 (3)
C1—C2—C3—I1	−174.98 (17)	C14—C9—C10—C11	−1.4 (4)
C9—N1—C4—C3	−174.5 (2)	N1—C9—C10—C11	−178.7 (2)
C9—N1—C4—C5	5.2 (4)	C9—C10—C11—C12	−2.0 (4)
C2—C3—C4—N1	175.8 (2)	C15—O2—C12—C11	176.3 (3)
I1—C3—C4—N1	−1.1 (3)	C15—O2—C12—C13	−4.2 (4)
C2—C3—C4—C5	−3.9 (4)	C10—C11—C12—O2	−177.1 (2)
I1—C3—C4—C5	179.19 (17)	C10—C11—C12—C13	3.3 (4)
N1—C4—C5—C6	151.7 (2)	O2—C12—C13—C14	179.2 (2)
C3—C4—C5—C6	−28.6 (3)	C11—C12—C13—C14	−1.3 (4)
C4—C5—C6—C8	−67.4 (3)	C10—C9—C14—C13	3.4 (4)
C4—C5—C6—C1	53.4 (3)	N1—C9—C14—C13	−179.4 (2)
C4—C5—C6—C7	172.1 (2)	C12—C13—C14—C9	−2.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.39	3.313 (3)	174
N1—H1···I1	0.86	2.71	3.227 (2)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.93	2.39	3.313 (3)	174
N1—H1⋯I1	0.86	2.71	3.227 (2)	120

Symmetry code: (i) .