2-Iodo-3-meth-oxy-6-methyl-pyridine.

The title compound, C(7)H(8)INO, which crystallizes with three independent mol-ecules in the asymmetric unit, was prepared by the reaction of 3-meth-oxy-6-methyl-pyridine with KI and I(2) in tetra-hydro-furan solution. In the crystal structure, the three independent mol-ecules are arranged in a similar orientation with the three polar meth-oxy groups aligned on one side and the three non-polar methyl groups on the other side. The three mol-ecules, excluding methyl H atoms, are essentially planar, with r.m.s. deviations of 0.0141 (1), 0.0081 (1) and 0.0066 (2)Å. The three pyridine rings make dihedral angles of 58.09 (3) 66.64 (4) and 71.5 (3)°. The crystal structure features rather weak inter-molecular C-H⋯O hydrogen bonds, which link two mol-ecules into dimers, and short I⋯N contacts [4.046 (3) Å].

Related literature

For C—C bond formation reactions, see: Vlad & Horvath (2002 ▶). For related structures, see: Bunker et al. (2009 ▶); Tahir et al. (2009 ▶).

Experimental

Crystal data

C7H8INO

M = 249.04

Triclinic,

a = 7.7974 (9) Å

b = 10.8302 (12) Å

c = 16.2898 (18) Å

α = 106.093 (1)°

β = 90.633 (1)°

γ = 103.636 (1)°

V = 1280.2 (2) Å3

Z = 6

Mo Kα radiation

μ = 3.69 mm−1

T = 296 K

0.20 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.526, T max = 0.646

9886 measured reflections

4737 independent reflections

3719 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.062

S = 1.01

4737 reflections

278 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050739/bq2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050739/bq2179Isup2.hkl

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

C7H8INO	Z = 6
Mr = 249.04	F(000) = 708
Triclinic, P1	Dx = 1.938 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7974 (9) Å	Cell parameters from 3296 reflections
b = 10.8302 (12) Å	θ = 2.7–23.1°
c = 16.2898 (18) Å	µ = 3.69 mm−1
α = 106.093 (1)°	T = 296 K
β = 90.633 (1)°	Block, colorless
γ = 103.636 (1)°	0.20 × 0.14 × 0.13 mm
V = 1280.2 (2) Å3

Bruker APEXII CCD diffractometer	4737 independent reflections
Radiation source: fine-focus sealed tube	3719 reflections with I > 2σ(I)
graphite	Rint = 0.026
phi and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.526, Tmax = 0.646	k = −12→13
9886 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0183P)2 + 0.8733P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4737 reflections	Δρmax = 0.56 e Å−3
278 parameters	Δρmin = −0.68 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (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	0.2655 (6)	0.5314 (4)	0.5640 (3)	0.0522 (10)
C2	0.3438 (6)	0.6096 (5)	0.5130 (3)	0.0581 (11)
C3	0.3160 (7)	0.5495 (6)	0.4251 (3)	0.0776 (15)
H3	0.3633	0.5957	0.3870	0.093*
C4	0.2179 (7)	0.4212 (6)	0.3958 (3)	0.0801 (15)
H4	0.2010	0.3797	0.3371	0.096*
C5	0.1440 (6)	0.3525 (5)	0.4509 (3)	0.0652 (13)
C6	0.0322 (8)	0.2131 (5)	0.4196 (3)	0.0905 (17)
H6A	0.0896	0.1550	0.4380	0.136*
H6B	0.0167	0.1866	0.3581	0.136*
H6C	−0.0813	0.2084	0.4425	0.136*
C7	0.5208 (8)	0.8131 (5)	0.4975 (4)	0.0900 (17)
H7A	0.5924	0.7653	0.4600	0.135*
H7B	0.5938	0.8961	0.5321	0.135*
H7C	0.4311	0.8294	0.4639	0.135*
C8	0.5213 (6)	0.3742 (4)	0.0739 (2)	0.0479 (10)
C9	0.6383 (6)	0.4983 (4)	0.0899 (3)	0.0500 (10)
C10	0.5793 (7)	0.6050 (4)	0.1397 (3)	0.0627 (12)
H10	0.6521	0.6906	0.1541	0.075*
C11	0.4127 (7)	0.5816 (5)	0.1669 (3)	0.0671 (13)
H11	0.3725	0.6521	0.2004	0.081*
C12	0.3034 (6)	0.4552 (5)	0.1456 (3)	0.0596 (11)
C13	0.1181 (7)	0.4251 (5)	0.1713 (3)	0.0791 (15)
H13A	0.0364	0.4120	0.1233	0.119*
H13B	0.1029	0.4979	0.2176	0.119*
H13C	0.0959	0.3460	0.1894	0.119*
C14	0.9152 (7)	0.6345 (4)	0.0738 (3)	0.0765 (15)
H14A	0.8591	0.6908	0.0527	0.115*
H14B	1.0216	0.6276	0.0458	0.115*
H14C	0.9438	0.6715	0.1345	0.115*
C15	0.1107 (5)	0.9067 (4)	0.2665 (2)	0.0450 (9)
C16	0.2909 (5)	0.9519 (4)	0.2630 (3)	0.0483 (10)
C17	0.3429 (6)	1.0324 (4)	0.2107 (3)	0.0624 (12)
H17	0.4627	1.0660	0.2063	0.075*
C18	0.2179 (7)	1.0628 (4)	0.1653 (3)	0.0646 (12)
H18	0.2528	1.1183	0.1308	0.077*
C19	0.0416 (6)	1.0116 (4)	0.1705 (3)	0.0594 (11)
C20	−0.1023 (7)	1.0386 (6)	0.1207 (4)	0.0880 (17)
H20A	−0.1829	0.9561	0.0903	0.132*
H20B	−0.0505	1.0840	0.0807	0.132*
H20C	−0.1652	1.0928	0.1596	0.132*
C21	0.5866 (6)	0.9547 (5)	0.3028 (4)	0.0871 (17)
H21A	0.6098	0.9276	0.2436	0.131*
H21B	0.6499	0.9151	0.3351	0.131*
H21C	0.6248	1.0495	0.3247	0.131*
I1	0.30556 (5)	0.61072 (3)	0.698542 (19)	0.07157 (13)
I2	0.60344 (4)	0.20520 (3)	0.00399 (2)	0.06819 (12)
I3	0.01400 (4)	0.78330 (3)	0.344715 (19)	0.05933 (11)
N1	0.1683 (5)	0.4079 (4)	0.5349 (2)	0.0568 (9)
N2	0.3602 (5)	0.3508 (3)	0.0991 (2)	0.0538 (9)
N3	−0.0123 (4)	0.9329 (3)	0.2220 (2)	0.0526 (9)
O1	0.4377 (4)	0.7353 (3)	0.5523 (2)	0.0727 (9)
O2	0.7978 (4)	0.5059 (3)	0.05666 (19)	0.0619 (8)
O3	0.3999 (4)	0.9124 (3)	0.3106 (2)	0.0648 (8)

	U11	U22	U33	U12	U13	U23
C1	0.059 (3)	0.060 (3)	0.043 (2)	0.024 (2)	0.006 (2)	0.016 (2)
C2	0.058 (3)	0.071 (3)	0.058 (3)	0.027 (2)	0.010 (2)	0.028 (2)
C3	0.080 (4)	0.103 (4)	0.060 (3)	0.028 (3)	0.011 (3)	0.036 (3)
C4	0.096 (4)	0.098 (4)	0.043 (3)	0.029 (4)	0.001 (3)	0.012 (3)
C5	0.065 (3)	0.071 (3)	0.056 (3)	0.024 (3)	−0.006 (2)	0.005 (2)
C6	0.106 (4)	0.082 (4)	0.069 (3)	0.022 (3)	−0.012 (3)	0.000 (3)
C7	0.091 (4)	0.091 (4)	0.104 (4)	0.014 (3)	0.018 (3)	0.061 (4)
C8	0.062 (3)	0.040 (2)	0.045 (2)	0.017 (2)	−0.005 (2)	0.0143 (18)
C9	0.061 (3)	0.042 (2)	0.046 (2)	0.013 (2)	−0.008 (2)	0.0104 (19)
C10	0.081 (3)	0.043 (2)	0.060 (3)	0.016 (2)	0.002 (3)	0.008 (2)
C11	0.092 (4)	0.058 (3)	0.058 (3)	0.034 (3)	0.009 (3)	0.014 (2)
C12	0.065 (3)	0.069 (3)	0.056 (3)	0.028 (3)	0.005 (2)	0.026 (2)
C13	0.076 (4)	0.100 (4)	0.074 (3)	0.035 (3)	0.017 (3)	0.035 (3)
C14	0.079 (4)	0.053 (3)	0.079 (3)	−0.005 (3)	0.003 (3)	0.008 (3)
C15	0.046 (2)	0.035 (2)	0.050 (2)	0.0075 (18)	0.0084 (19)	0.0084 (18)
C16	0.045 (2)	0.039 (2)	0.058 (3)	0.0087 (19)	0.004 (2)	0.0093 (19)
C17	0.052 (3)	0.047 (3)	0.083 (3)	0.003 (2)	0.017 (2)	0.017 (2)
C18	0.068 (3)	0.052 (3)	0.077 (3)	0.006 (2)	0.015 (3)	0.032 (2)
C19	0.069 (3)	0.050 (3)	0.058 (3)	0.011 (2)	0.002 (2)	0.017 (2)
C20	0.083 (4)	0.095 (4)	0.098 (4)	0.016 (3)	−0.008 (3)	0.054 (3)
C21	0.047 (3)	0.090 (4)	0.128 (5)	0.012 (3)	0.003 (3)	0.041 (4)
I1	0.0894 (3)	0.0652 (2)	0.04841 (18)	0.00163 (17)	0.00875 (16)	0.01222 (15)
I2	0.0630 (2)	0.03952 (17)	0.0968 (3)	0.01431 (14)	0.00303 (17)	0.01007 (16)
I3	0.05512 (19)	0.0623 (2)	0.0677 (2)	0.01301 (14)	0.01072 (14)	0.03120 (15)
N1	0.064 (2)	0.057 (2)	0.050 (2)	0.0183 (19)	0.0019 (18)	0.0131 (18)
N2	0.057 (2)	0.056 (2)	0.057 (2)	0.0195 (18)	0.0023 (18)	0.0244 (18)
N3	0.049 (2)	0.045 (2)	0.061 (2)	0.0090 (16)	0.0021 (17)	0.0147 (17)
O1	0.079 (2)	0.066 (2)	0.076 (2)	0.0091 (18)	0.0111 (18)	0.0331 (18)
O2	0.0599 (19)	0.0423 (16)	0.0701 (19)	0.0027 (14)	0.0029 (16)	0.0033 (14)
O3	0.0402 (16)	0.069 (2)	0.087 (2)	0.0107 (15)	0.0047 (15)	0.0270 (17)

C1—N1	1.323 (5)	C12—N2	1.348 (5)
C1—C2	1.392 (6)	C12—C13	1.496 (6)
C1—I1	2.110 (4)	C13—H13A	0.9600
C2—O1	1.355 (5)	C13—H13B	0.9600
C2—C3	1.390 (6)	C13—H13C	0.9600
C3—C4	1.366 (7)	C14—O2	1.426 (5)
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.368 (7)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—N1	1.324 (5)	C15—N3	1.324 (5)
C5—C6	1.497 (7)	C15—C16	1.382 (5)
C6—H6A	0.9600	C15—I3	2.114 (4)
C6—H6B	0.9600	C16—O3	1.359 (5)
C6—H6C	0.9600	C16—C17	1.380 (6)
C7—O1	1.449 (5)	C17—C18	1.369 (6)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—C19	1.369 (6)
C7—H7C	0.9600	C18—H18	0.9300
C8—N2	1.315 (5)	C19—N3	1.357 (5)
C8—C9	1.389 (5)	C19—C20	1.506 (6)
C8—I2	2.115 (4)	C20—H20A	0.9600
C9—O2	1.356 (5)	C20—H20B	0.9600
C9—C10	1.394 (6)	C20—H20C	0.9600
C10—C11	1.367 (6)	C21—O3	1.438 (5)
C10—H10	0.9300	C21—H21A	0.9600
C11—C12	1.379 (6)	C21—H21B	0.9600
C11—H11	0.9300	C21—H21C	0.9600
N1—C1—C2	125.0 (4)	H13A—C13—H13B	109.5
N1—C1—I1	116.1 (3)	C12—C13—H13C	109.5
C2—C1—I1	118.9 (3)	H13A—C13—H13C	109.5
O1—C2—C3	126.1 (4)	H13B—C13—H13C	109.5
O1—C2—C1	118.2 (4)	O2—C14—H14A	109.5
C3—C2—C1	115.6 (5)	O2—C14—H14B	109.5
C4—C3—C2	118.8 (5)	H14A—C14—H14B	109.5
C4—C3—H3	120.6	O2—C14—H14C	109.5
C2—C3—H3	120.6	H14A—C14—H14C	109.5
C3—C4—C5	121.4 (5)	H14B—C14—H14C	109.5
C3—C4—H4	119.3	N3—C15—C16	124.5 (4)
C5—C4—H4	119.3	N3—C15—I3	115.2 (3)
N1—C5—C4	120.8 (5)	C16—C15—I3	120.3 (3)
N1—C5—C6	117.3 (5)	O3—C16—C17	126.2 (4)
C4—C5—C6	122.0 (5)	O3—C16—C15	117.2 (4)
C5—C6—H6A	109.5	C17—C16—C15	116.6 (4)
C5—C6—H6B	109.5	C18—C17—C16	119.8 (4)
H6A—C6—H6B	109.5	C18—C17—H17	120.1
C5—C6—H6C	109.5	C16—C17—H17	120.1
H6A—C6—H6C	109.5	C19—C18—C17	120.2 (4)
H6B—C6—H6C	109.5	C19—C18—H18	119.9
O1—C7—H7A	109.5	C17—C18—H18	119.9
O1—C7—H7B	109.5	N3—C19—C18	120.8 (4)
H7A—C7—H7B	109.5	N3—C19—C20	116.4 (4)
O1—C7—H7C	109.5	C18—C19—C20	122.8 (4)
H7A—C7—H7C	109.5	C19—C20—H20A	109.5
H7B—C7—H7C	109.5	C19—C20—H20B	109.5
N2—C8—C9	125.6 (4)	H20A—C20—H20B	109.5
N2—C8—I2	115.6 (3)	C19—C20—H20C	109.5
C9—C8—I2	118.8 (3)	H20A—C20—H20C	109.5
O2—C9—C8	118.2 (4)	H20B—C20—H20C	109.5
O2—C9—C10	125.8 (4)	O3—C21—H21A	109.5
C8—C9—C10	116.0 (4)	O3—C21—H21B	109.5
C11—C10—C9	118.9 (4)	H21A—C21—H21B	109.5
C11—C10—H10	120.6	O3—C21—H21C	109.5
C9—C10—H10	120.6	H21A—C21—H21C	109.5
C10—C11—C12	121.0 (4)	H21B—C21—H21C	109.5
C10—C11—H11	119.5	C1—N1—C5	118.3 (4)
C12—C11—H11	119.5	C8—N2—C12	117.8 (4)
N2—C12—C11	120.6 (4)	C15—N3—C19	118.0 (4)
N2—C12—C13	116.3 (4)	C2—O1—C7	116.9 (4)
C11—C12—C13	123.1 (4)	C9—O2—C14	117.1 (3)
C12—C13—H13A	109.5	C16—O3—C21	116.5 (4)
C12—C13—H13B	109.5
N1—C1—C2—O1	179.0 (4)	C15—C16—C17—C18	−0.4 (6)
I1—C1—C2—O1	−2.2 (5)	C16—C17—C18—C19	−1.1 (7)
N1—C1—C2—C3	−0.6 (7)	C17—C18—C19—N3	1.5 (7)
I1—C1—C2—C3	178.2 (3)	C17—C18—C19—C20	−178.5 (5)
O1—C2—C3—C4	179.9 (5)	C2—C1—N1—C5	0.8 (6)
C1—C2—C3—C4	−0.5 (7)	I1—C1—N1—C5	−178.0 (3)
C2—C3—C4—C5	1.5 (8)	C4—C5—N1—C1	0.1 (7)
C3—C4—C5—N1	−1.3 (8)	C6—C5—N1—C1	−179.5 (4)
C3—C4—C5—C6	178.4 (5)	C9—C8—N2—C12	−1.1 (6)
N2—C8—C9—O2	−177.6 (4)	I2—C8—N2—C12	178.5 (3)
I2—C8—C9—O2	2.8 (5)	C11—C12—N2—C8	−1.1 (6)
N2—C8—C9—C10	2.5 (6)	C13—C12—N2—C8	178.6 (4)
I2—C8—C9—C10	−177.2 (3)	C16—C15—N3—C19	−1.5 (6)
O2—C9—C10—C11	178.5 (4)	I3—C15—N3—C19	−180.0 (3)
C8—C9—C10—C11	−1.6 (6)	C18—C19—N3—C15	−0.3 (6)
C9—C10—C11—C12	−0.4 (7)	C20—C19—N3—C15	179.8 (4)
C10—C11—C12—N2	1.8 (7)	C3—C2—O1—C7	−1.8 (7)
C10—C11—C12—C13	−177.9 (4)	C1—C2—O1—C7	178.7 (4)
N3—C15—C16—O3	−177.8 (3)	C8—C9—O2—C14	179.8 (4)
I3—C15—C16—O3	0.7 (5)	C10—C9—O2—C14	−0.3 (6)
N3—C15—C16—C17	1.8 (6)	C17—C16—O3—C21	−2.6 (6)
I3—C15—C16—C17	−179.7 (3)	C15—C16—O3—C21	177.0 (4)
O3—C16—C17—C18	179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2i	0.96	2.56	3.429 (6)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2i	0.96	2.56	3.429 (6)	151

Symmetry code: (i) .