5,7-Diiodo­quinolin-8-ol

The title compound, C₉H₅I₂NO, features an almost planar mol­ecule. Geometric parameters are in the usual ranges. The crystal packing shows that two hydrogen-bonded mol­ecules are related by a twofold rotation axis.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.006 Å
• R factor = 0.031
• wR factor = 0.077
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON.

5,7-Diiodoquinolin-8-ol

Crystal data

C9H5I2NO	F(000) = 720
Mr = 396.94	Dx = 2.703 Mg m^−3
Monoclinic, P2/c	Melting point: 472(1) K
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.1699 (13) Å	Cell parameters from 7152 reflections
b = 4.2915 (4) Å	θ = 3.6–27.2°
c = 16.1565 (13) Å	µ = 6.40 mm^−1
β = 96.801 (7)°	T = 173 K
V = 975.57 (15) Å^3	Rod, yellow
Z = 4	0.31 × 0.11 × 0.10 mm

Data collection

Stoe IPDS-II two-circle diffractometer	2244 independent reflections
Radiation source: fine-focus sealed tube	2163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −18→18
Tmin = 0.318, Tmax = 0.527	k = −5→5
7396 measured reflections	l = −20→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0385P)^2 + 2.4632P] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max = 0.001
2244 reflections	Δρmax = 1.25 e Å^−3
120 parameters	Δρmin = −1.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.199166 (19)	1.16860 (6)	0.595651 (15)	0.02198 (12)
I2	0.062028 (18)	0.50962 (6)	0.884895 (17)	0.02272 (12)
O1	0.3950 (2)	0.8966 (8)	0.68130 (19)	0.0244 (6)
H1	0.4428	0.7834	0.6942	0.029*
C1	0.3270 (3)	0.8246 (9)	0.7300 (2)	0.0179 (7)
C2	0.2343 (3)	0.9234 (9)	0.7074 (2)	0.0168 (7)
C3	0.1599 (3)	0.8430 (9)	0.7548 (2)	0.0167 (7)
H3	0.0975	0.9198	0.7390	0.020*
C4	0.1780 (3)	0.6540 (9)	0.8236 (2)	0.0168 (7)
C5	0.2723 (3)	0.5472 (9)	0.8502 (2)	0.0159 (7)
C6	0.3471 (3)	0.6446 (9)	0.8039 (2)	0.0178 (7)
N7	0.4399 (3)	0.5647 (9)	0.8275 (2)	0.0211 (7)
C8	0.4603 (3)	0.3821 (11)	0.8938 (3)	0.0244 (8)
H8	0.5248	0.3261	0.9097	0.029*
C9	0.3907 (3)	0.2676 (11)	0.9418 (3)	0.0228 (8)
H9	0.4081	0.1343	0.9880	0.027*
C10	0.2973 (3)	0.3523 (10)	0.9205 (3)	0.0206 (8)
H10	0.2497	0.2806	0.9526	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02860 (18)	0.02110 (17)	0.01693 (16)	0.00530 (10)	0.00559 (10)	0.00259 (9)
I2	0.01802 (17)	0.02671 (18)	0.02479 (17)	−0.00249 (9)	0.00822 (11)	0.00300 (10)
O1	0.0171 (13)	0.0334 (16)	0.0241 (14)	0.0032 (13)	0.0079 (11)	0.0093 (14)
C1	0.0193 (18)	0.0184 (18)	0.0166 (17)	−0.0029 (14)	0.0044 (14)	−0.0008 (15)
C2	0.0219 (19)	0.0141 (16)	0.0146 (16)	−0.0002 (14)	0.0023 (14)	−0.0009 (14)
C3	0.0138 (16)	0.0178 (17)	0.0185 (17)	−0.0010 (13)	0.0016 (13)	−0.0024 (14)
C4	0.0131 (17)	0.0203 (18)	0.0176 (17)	−0.0038 (13)	0.0048 (13)	−0.0040 (15)
C5	0.0169 (17)	0.0154 (16)	0.0154 (16)	−0.0031 (14)	0.0019 (13)	−0.0011 (14)
C6	0.0161 (17)	0.0189 (18)	0.0187 (17)	−0.0014 (14)	0.0026 (13)	−0.0052 (15)
N7	0.0188 (16)	0.0257 (17)	0.0191 (16)	0.0013 (14)	0.0039 (13)	−0.0005 (14)
C8	0.0211 (19)	0.028 (2)	0.0237 (19)	0.0050 (17)	0.0008 (15)	−0.0021 (18)
C9	0.024 (2)	0.0229 (19)	0.0203 (19)	0.0025 (16)	−0.0005 (15)	0.0028 (16)
C10	0.024 (2)	0.0211 (19)	0.0170 (17)	−0.0013 (15)	0.0043 (14)	0.0006 (16)

Geometric parameters (Å, º)

I1—C2	2.098 (4)	C5—C10	1.420 (6)
I2—C4	2.110 (4)	C5—C6	1.430 (5)
O1—C1	1.350 (5)	C6—N7	1.370 (5)
O1—H1	0.8400	N7—C8	1.332 (6)
C1—C2	1.388 (6)	C8—C9	1.413 (6)
C1—C6	1.421 (6)	C8—H8	0.9500
C2—C3	1.417 (5)	C9—C10	1.376 (6)
C3—C4	1.375 (6)	C9—H9	0.9500
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.430 (5)
C1—O1—H1	109.5	C4—C5—C6	118.2 (4)
O1—C1—C2	119.7 (4)	N7—C6—C1	117.4 (4)
O1—C1—C6	121.9 (4)	N7—C6—C5	121.8 (4)
C2—C1—C6	118.4 (4)	C1—C6—C5	120.8 (4)
C1—C2—C3	121.6 (4)	C8—N7—C6	118.8 (4)
C1—C2—I1	120.1 (3)	N7—C8—C9	123.2 (4)
C3—C2—I1	118.1 (3)	N7—C8—H8	118.4
C4—C3—C2	120.1 (3)	C9—C8—H8	118.4
C4—C3—H3	120.0	C10—C9—C8	119.0 (4)
C2—C3—H3	120.0	C10—C9—H9	120.5
C3—C4—C5	120.7 (3)	C8—C9—H9	120.5
C3—C4—I2	118.2 (3)	C9—C10—C5	119.8 (4)
C5—C4—I2	121.1 (3)	C9—C10—H10	120.1
C10—C5—C4	124.4 (4)	C5—C10—H10	120.1
C10—C5—C6	117.4 (4)
O1—C1—C2—C3	177.5 (4)	O1—C1—C6—C5	−174.2 (4)
C6—C1—C2—C3	−1.5 (6)	C2—C1—C6—C5	4.7 (6)
O1—C1—C2—I1	2.3 (5)	C10—C5—C6—N7	−2.5 (6)
C6—C1—C2—I1	−176.6 (3)	C4—C5—C6—N7	176.9 (4)
C1—C2—C3—C4	−2.2 (6)	C10—C5—C6—C1	176.3 (4)
I1—C2—C3—C4	173.0 (3)	C4—C5—C6—C1	−4.3 (6)
C2—C3—C4—C5	2.7 (6)	C1—C6—N7—C8	−176.4 (4)
C2—C3—C4—I2	−174.5 (3)	C5—C6—N7—C8	2.4 (6)
C3—C4—C5—C10	179.9 (4)	C6—N7—C8—C9	−0.5 (7)
I2—C4—C5—C10	−3.0 (6)	N7—C8—C9—C10	−1.3 (7)
C3—C4—C5—C6	0.5 (6)	C8—C9—C10—C5	1.2 (7)
I2—C4—C5—C6	177.6 (3)	C4—C5—C10—C9	−178.7 (4)
O1—C1—C6—N7	4.7 (6)	C6—C5—C10—C9	0.6 (6)
C2—C1—C6—N7	−176.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N7^i	0.84	1.98	2.757 (5)	154

Symmetry code: (i) −x+1, y, −z+3/2.