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

Manvizhi, K.; Chakkaravarthi, G.; Anbalagan, G.; Rajagopal, G.

doi:10.1107/S1600536811034519

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2500

doi:10.1107/S1600536811034519

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

K. Manvizhi,^a G. Chakkaravarthi,^b ^* G. Anbalagan ^c and G. Rajagopal ^d ^*

^aDepartment of Chemistry, Anand Institute of Higher Technology, Kazhipattur, Chennai 603 103, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^dDepartment of Chemistry, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 18 August 2011; accepted 22 August 2011; online 27 August 2011)

In the title compound, C₁₇H₁₆I₂N₂O₂, the two aromatic rings are almost coplanar [dihedral angle 2.57 (15)°]. The morpholine ring adopts a chair conformation. The molecular structure is stabilized by an O—H⋯N hydrogen bond and the crystal packing exhibits weak intermolecular C—H⋯O and π–π [centroid-to-centroid distances 3.663 (3)-4.073 (3) Å] interactions.

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_r = 534.12
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.113
S = 1.16
7647 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 1.22 e Å⁻³
Δρ_min = −1.72 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034519/bt5621sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811034519/bt5621Isup3.cml

checkCIF report

Comment top

Morpholine derivatives possess anticancer and antimicrobial (Lan et al., 2010; Raparti et al., 2009) activities. In the title compound, (I) (Fig. 1), The bond lengths C═N [1.282 (6)Å], C—I [C1—I1 = 2.092 (4) and C5—I2 = 2.097 (4) Å] are comparable with the literature values and the bond lengths of the morpholine ring are agree well with a reported related structure (Yang et al., 2011).

The mean planes of two benzene rings (C8–C13) and (C1–C6) are oriented at an angle of 2.57 (15)°. The morpholine ring adopts a chair conformation [Puckering parameters are Q = 0.544 (6)Å, θ = 170.8 (5)° and ϕ = 180 (4)° (Cremer & Pople, 1975) for the ring (O1/C15/C14/N2/C17/C16)].

The molecular structure is stabilized by O—H···N hydrogen bonding and the crystal packing exhibit weak intermolecular C—H···O (Fig. 2 and Table 1) and π–π [Cg2···Cg3(-x, -y, -z) distance of 3.663 (3)Å; Cg2···Cg3(-x, 1 - y, -z) distance of 4.074 (3)Å] interactions.

Related literature top

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 top

An ethanolic solution (20 ml) of 4-(4-aminophenyl)morpholine (10 mmol) was magnetically stirred in a round bottom flask followed by drop wise addition of ethanolic solution of 3,5-diiodosalicylaldehyde (10 mmol). The reaction mixture was then refluxed for 3 h and upon cooling to 273 K, a red crystalline solid precipitates from the mixture. The solid which is separated out was filtered washed with ice cold ethanol and dried in vaccuo over anhydrous CaCl₂. Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature. m.p. 443 K.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the c axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

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

Crystal data top

C₁₇H₁₆I₂N₂O₂	F(000) = 2032
M_r = 534.12	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0134P)² + 27.6528P] where P = (F_o² + 2F_c²)/3
7647 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 1.22 e Å⁻³
0 restraints	Δρ_min = −1.72 e Å⁻³

Crystal data top

C₁₇H₁₆I₂N₂O₂	V = 3647.4 (4) Å³
M_r = 534.12	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.4133 (16) Å	µ = 3.46 mm⁻¹
b = 7.6598 (4) Å	T = 295 K
c = 18.0332 (11) Å	0.26 × 0.20 × 0.20 mm
β = 91.417 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	7647 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4855 reflections with I > 2σ(I)
T_min = 0.467, T_max = 0.545	R_int = 0.023
17839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0134P)² + 27.6528P] where P = (F_o² + 2F_c²)/3
7647 reflections	Δρ_max = 1.22 e Å⁻³
208 parameters	Δρ_min = −1.72 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆I₂N₂O₂
M_r	534.12
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	26.4133 (16), 7.6598 (4), 18.0332 (11)
β (°)	91.417 (2)
V (Å³)	3647.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.46
Crystal size (mm)	0.26 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.467, 0.545
No. of measured, independent and observed [I > 2σ(I)] reflections	17839, 7647, 4855
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.824

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.113, 1.16
No. of reflections	7647
No. of parameters	208
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0134P)² + 27.6528P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.22, −1.72

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

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