2,4-Diiodo-6-{[4-(morpholin-4-yl)phenyl]iminomethyl}phenol.

In the title compound, C(17)H(16)I(2)N(2)O(2), the two aromatic rings are almost coplanar [dihedral angle 2.57 (15)°]. The morpholine ring adopts a chair conformation. The mol-ecular structure is stabilized by an O-H⋯N hydrogen bond and the crystal packing exhibits weak inter-molecular C-H⋯O and π-π [centroid-to-centroid distances 3.663 (3)-4.073 (3) Å] inter-actions.

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010 ▶); Raparti et al.(2009 ▶). For a related structure, see: Yang et al. (2011 ▶). For the definition of puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H16I2N2O2

M = 534.12

Monoclinic,

a = 26.4133 (16) Å

b = 7.6598 (4) Å

c = 18.0332 (11) Å

β = 91.417 (2)°

V = 3647.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 3.46 mm−1

T = 295 K

0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.467, T max = 0.545

17839 measured reflections

7647 independent reflections

4855 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.113

S = 1.16

7647 reflections

208 parameters

H-atom parameters constrained

Δρmax = 1.22 e Å−3

Δρmin = −1.72 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034519/bt5621sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034519/bt5621Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034519/bt5621Isup3.cml

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

C17H16I2N2O2	F(000) = 2032
Mr = 534.12	Dx = 1.945 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6743 reflections
a = 26.4133 (16) Å	θ = 2.7–35.4°
b = 7.6598 (4) Å	µ = 3.46 mm−1
c = 18.0332 (11) Å	T = 295 K
β = 91.417 (2)°	Block, colourless
V = 3647.4 (4) Å3	0.26 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII diffractometer	7647 independent reflections
Radiation source: fine-focus sealed tube	4855 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 35.9°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −42→42
Tmin = 0.467, Tmax = 0.545	k = −5→12
17839 measured reflections	l = −29→27

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0134P)2 + 27.6528P] where P = (Fo2 + 2Fc2)/3
7647 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 1.22 e Å−3
0 restraints	Δρmin = −1.72 e Å−3

	x	y	z	Uiso*/Ueq
I1	0.198728 (14)	−0.04313 (7)	0.01153 (2)	0.06368 (14)
I2	0.097444 (12)	−0.01689 (5)	0.305807 (16)	0.04538 (10)
O1	−0.25208 (14)	0.6183 (6)	−0.2595 (3)	0.0645 (11)
O2	0.09297 (14)	0.1239 (6)	−0.03377 (17)	0.0567 (10)
H2	0.0683	0.1836	−0.0453	0.085*
N1	0.00453 (14)	0.2516 (5)	−0.0214 (2)	0.0399 (9)
N2	−0.16015 (14)	0.5632 (5)	−0.1763 (2)	0.0425 (9)
C1	0.13595 (16)	0.0208 (6)	0.0746 (2)	0.0369 (9)
C2	0.09350 (17)	0.0948 (6)	0.0387 (2)	0.0373 (9)
C3	0.05152 (15)	0.1370 (6)	0.0821 (2)	0.0335 (9)
C4	0.05340 (16)	0.1049 (6)	0.1581 (2)	0.0361 (9)
H4	0.0257	0.1332	0.1867	0.043*
C5	0.09549 (15)	0.0320 (6)	0.1913 (2)	0.0329 (9)
C6	0.13743 (15)	−0.0108 (6)	0.1495 (2)	0.0337 (9)
H6	0.1660	−0.0601	0.1721	0.040*
C7	0.00713 (17)	0.2167 (6)	0.0481 (3)	0.0395 (10)
H7	−0.0203	0.2434	0.0775	0.047*
C8	−0.03754 (17)	0.3331 (6)	−0.0573 (3)	0.0396 (10)
C9	−0.03566 (18)	0.3557 (7)	−0.1329 (3)	0.0450 (11)
H9	−0.0070	0.3202	−0.1577	0.054*
C10	−0.07575 (19)	0.4305 (7)	−0.1727 (3)	0.0462 (11)
H10	−0.0735	0.4440	−0.2238	0.055*
C11	−0.11929 (17)	0.4858 (6)	−0.1375 (3)	0.0402 (10)
C12	−0.12009 (19)	0.4645 (8)	−0.0609 (3)	0.0505 (13)
H12	−0.1483	0.5023	−0.0355	0.061*
C13	−0.0805 (2)	0.3894 (8)	−0.0215 (3)	0.0520 (13)
H13	−0.0825	0.3762	0.0296	0.062*
C14	−0.1627 (2)	0.5380 (8)	−0.2559 (3)	0.0591 (15)
H14A	−0.1692	0.4159	−0.2668	0.071*
H14B	−0.1305	0.5691	−0.2768	0.071*
C15	−0.2046 (2)	0.6497 (9)	−0.2912 (4)	0.0682 (18)
H15A	−0.1959	0.7720	−0.2852	0.082*
H15B	−0.2069	0.6250	−0.3440	0.082*
C16	−0.2480 (2)	0.6635 (9)	−0.1835 (4)	0.0655 (17)
H16A	−0.2807	0.6489	−0.1611	0.079*
H16B	−0.2385	0.7855	−0.1791	0.079*
C17	−0.20944 (19)	0.5535 (8)	−0.1423 (3)	0.0573 (15)
H17A	−0.2064	0.5932	−0.0913	0.069*
H17B	−0.2208	0.4331	−0.1419	0.069*

	U11	U22	U33	U12	U13	U23
I1	0.04506 (19)	0.1026 (4)	0.04403 (18)	0.0186 (2)	0.01452 (14)	−0.0004 (2)
I2	0.04006 (15)	0.0669 (2)	0.02930 (13)	0.00174 (15)	0.00371 (10)	0.00684 (14)
O1	0.0412 (19)	0.067 (3)	0.084 (3)	−0.0058 (19)	−0.0255 (19)	0.011 (2)
O2	0.059 (2)	0.086 (3)	0.0255 (15)	0.027 (2)	0.0000 (14)	−0.0027 (17)
N1	0.0382 (19)	0.044 (2)	0.0372 (19)	0.0059 (17)	−0.0102 (16)	−0.0042 (17)
N2	0.0365 (19)	0.037 (2)	0.053 (2)	−0.0016 (16)	−0.0128 (17)	0.0076 (18)
C1	0.0314 (19)	0.050 (3)	0.0293 (18)	0.0038 (19)	0.0014 (15)	−0.0053 (19)
C2	0.039 (2)	0.045 (3)	0.0277 (19)	0.000 (2)	−0.0013 (16)	−0.0041 (18)
C3	0.0301 (19)	0.038 (2)	0.0325 (19)	0.0010 (17)	−0.0032 (16)	−0.0035 (17)
C4	0.0287 (19)	0.044 (3)	0.035 (2)	0.0003 (18)	0.0036 (16)	0.0006 (19)
C5	0.0327 (19)	0.041 (2)	0.0249 (16)	−0.0051 (18)	0.0025 (14)	0.0026 (17)
C6	0.0268 (17)	0.043 (2)	0.0316 (18)	0.0002 (17)	−0.0023 (14)	0.0017 (18)
C7	0.031 (2)	0.043 (3)	0.044 (2)	0.0021 (19)	−0.0029 (18)	−0.004 (2)
C8	0.035 (2)	0.039 (2)	0.044 (2)	0.0025 (19)	−0.0085 (18)	−0.001 (2)
C9	0.039 (2)	0.051 (3)	0.046 (3)	0.008 (2)	−0.004 (2)	−0.002 (2)
C10	0.044 (3)	0.052 (3)	0.042 (2)	0.007 (2)	−0.008 (2)	0.000 (2)
C11	0.034 (2)	0.034 (2)	0.052 (3)	−0.0049 (18)	−0.0112 (19)	0.004 (2)
C12	0.037 (2)	0.062 (3)	0.052 (3)	0.010 (2)	−0.002 (2)	0.004 (3)
C13	0.046 (3)	0.069 (4)	0.042 (3)	0.010 (3)	−0.002 (2)	0.006 (3)
C14	0.049 (3)	0.067 (4)	0.060 (3)	0.000 (3)	−0.016 (3)	0.014 (3)
C15	0.056 (3)	0.075 (4)	0.072 (4)	0.003 (3)	−0.024 (3)	0.019 (3)
C16	0.039 (3)	0.071 (4)	0.085 (5)	0.005 (3)	−0.017 (3)	0.012 (4)
C17	0.037 (2)	0.062 (4)	0.073 (4)	0.003 (2)	−0.010 (2)	0.011 (3)

I1—C1	2.092 (4)	C8—C9	1.376 (7)
I2—C5	2.097 (4)	C8—C13	1.387 (7)
O1—C15	1.412 (7)	C9—C10	1.389 (6)
O1—C16	1.415 (8)	C9—H9	0.9300
O2—C2	1.325 (5)	C10—C11	1.393 (7)
O2—H2	0.8200	C10—H10	0.9300
N1—C7	1.282 (6)	C11—C12	1.392 (7)
N1—C8	1.417 (6)	C12—C13	1.376 (7)
N2—C11	1.403 (6)	C12—H12	0.9300
N2—C14	1.447 (7)	C13—H13	0.9300
N2—C17	1.455 (7)	C14—C15	1.525 (7)
C1—C6	1.372 (6)	C14—H14A	0.9700
C1—C2	1.401 (6)	C14—H14B	0.9700
C2—C3	1.411 (6)	C15—H15A	0.9700
C3—C4	1.393 (6)	C15—H15B	0.9700
C3—C7	1.445 (6)	C16—C17	1.504 (7)
C4—C5	1.369 (6)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.394 (6)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—H7	0.9300
C15—O1—C16	107.7 (4)	C11—C10—H10	119.4
C2—O2—H2	109.5	C12—C11—C10	116.7 (4)
C7—N1—C8	124.1 (4)	C12—C11—N2	120.9 (5)
C11—N2—C14	117.0 (4)	C10—C11—N2	122.3 (5)
C11—N2—C17	117.0 (4)	C13—C12—C11	122.1 (5)
C14—N2—C17	113.0 (4)	C13—C12—H12	118.9
C6—C1—C2	122.0 (4)	C11—C12—H12	118.9
C6—C1—I1	119.4 (3)	C12—C13—C8	120.7 (5)
C2—C1—I1	118.6 (3)	C12—C13—H13	119.7
O2—C2—C1	120.9 (4)	C8—C13—H13	119.7
O2—C2—C3	121.3 (4)	N2—C14—C15	110.8 (5)
C1—C2—C3	117.8 (4)	N2—C14—H14A	109.5
C4—C3—C2	119.8 (4)	C15—C14—H14A	109.5
C4—C3—C7	120.1 (4)	N2—C14—H14B	109.5
C2—C3—C7	120.2 (4)	C15—C14—H14B	109.5
C5—C4—C3	120.8 (4)	H14A—C14—H14B	108.1
C5—C4—H4	119.6	O1—C15—C14	112.2 (5)
C3—C4—H4	119.6	O1—C15—H15A	109.2
C4—C5—C6	120.5 (4)	C14—C15—H15A	109.2
C4—C5—I2	120.2 (3)	O1—C15—H15B	109.2
C6—C5—I2	119.3 (3)	C14—C15—H15B	109.2
C1—C6—C5	119.2 (4)	H15A—C15—H15B	107.9
C1—C6—H6	120.4	O1—C16—C17	112.1 (5)
C5—C6—H6	120.4	O1—C16—H16A	109.2
N1—C7—C3	121.7 (4)	C17—C16—H16A	109.2
N1—C7—H7	119.1	O1—C16—H16B	109.2
C3—C7—H7	119.1	C17—C16—H16B	109.2
C9—C8—C13	118.1 (4)	H16A—C16—H16B	107.9
C9—C8—N1	117.4 (4)	N2—C17—C16	111.4 (5)
C13—C8—N1	124.4 (4)	N2—C17—H17A	109.3
C8—C9—C10	121.3 (5)	C16—C17—H17A	109.3
C8—C9—H9	119.4	N2—C17—H17B	109.3
C10—C9—H9	119.4	C16—C17—H17B	109.3
C9—C10—C11	121.1 (5)	H17A—C17—H17B	108.0
C9—C10—H10	119.4
C6—C1—C2—O2	−179.9 (5)	N1—C8—C9—C10	178.4 (5)
I1—C1—C2—O2	0.0 (7)	C8—C9—C10—C11	0.1 (8)
C6—C1—C2—C3	0.1 (7)	C9—C10—C11—C12	0.9 (8)
I1—C1—C2—C3	180.0 (3)	C9—C10—C11—N2	179.4 (5)
O2—C2—C3—C4	−179.9 (5)	C14—N2—C11—C12	−163.6 (5)
C1—C2—C3—C4	0.1 (7)	C17—N2—C11—C12	−24.8 (7)
O2—C2—C3—C7	−1.2 (7)	C14—N2—C11—C10	17.9 (7)
C1—C2—C3—C7	178.8 (4)	C17—N2—C11—C10	156.7 (5)
C2—C3—C4—C5	−0.2 (7)	C10—C11—C12—C13	−1.3 (8)
C7—C3—C4—C5	−178.9 (4)	N2—C11—C12—C13	−179.9 (5)
C3—C4—C5—C6	0.2 (7)	C11—C12—C13—C8	0.7 (9)
C3—C4—C5—I2	−179.6 (3)	C9—C8—C13—C12	0.4 (8)
C2—C1—C6—C5	−0.1 (7)	N1—C8—C13—C12	−178.8 (5)
I1—C1—C6—C5	180.0 (3)	C11—N2—C14—C15	−172.1 (5)
C4—C5—C6—C1	−0.1 (7)	C17—N2—C14—C15	47.5 (6)
I2—C5—C6—C1	179.8 (3)	C16—O1—C15—C14	61.6 (7)
C8—N1—C7—C3	−178.5 (4)	N2—C14—C15—O1	−55.3 (7)
C4—C3—C7—N1	178.5 (5)	C15—O1—C16—C17	−61.9 (6)
C2—C3—C7—N1	−0.2 (7)	C11—N2—C17—C16	171.5 (5)
C7—N1—C8—C9	−177.4 (5)	C14—N2—C17—C16	−48.1 (7)
C7—N1—C8—C13	1.7 (8)	O1—C16—C17—N2	55.7 (7)
C13—C8—C9—C10	−0.8 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.82	2.548 (5)	146
C6—H6···O1i	0.93	2.50	3.413 (5)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.82	2.548 (5)	146
C6—H6⋯O1i	0.93	2.50	3.413 (5)	166

Symmetry code: (i) .