2-[(2,6-Diisopropyl­phen­yl)imino­meth­yl]-4-iodo­phenol

Balamurugan, P.; Raja, K.K.; Bilal, I.M.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S1600536812023653

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1915

doi:10.1107/S1600536812023653

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2-[(2,6-Diisopropylphenyl)iminomethyl]-4-iodophenol

P. Balamurugan,^a K. Kanmani Raja,^b I. Mohammed Bilal,^c G. Chakkaravarthi ^d ^* and G. Rajagopal ^e ^*

^aDepartment of Chemistry, Government Arts College (Men), Nandanam, Chennai 600 035, India, ^bDepartment of Chemistry, Government Thirumagal Mills College, Gudiyattam 632 604, India, ^cDepartment of Chemistry, B.S. Abdur Rahman University, Vandalur, Chennai 600 049, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Chemistry, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 10 May 2012; accepted 24 May 2012; online 31 May 2012)

The asymmetric unit of title compound, C₁₉H₂₂INO, contains two independent molecules. Classical intramolecular O—H⋯N hydrogen bonds stabilize the molecular structures. The crystal structure is stabilized by weak intermolecular C—H⋯π and π–π [centroid–centroid = 3.8622 (18) Å] interactions. In both molecules, the aromatic rings are nearly perpendicular to each other [dihedral angles = 84.26 (17) and 86.69 (15)°].

Related literature

For the biological activity of Schiff base ligands, see: Santos et al. (2001 ). For related strucutures, see: Raja et al. (2008 ); Lin et al. (2005 ).

Experimental

Crystal data

C₁₉H₂₂INO
M_r = 407.28
Triclinic, $[P \overline 1]$
a = 5.9891 (2) Å
b = 12.4270 (5) Å
c = 25.8832 (10) Å
α = 83.065 (2)°
β = 84.860 (3)°
γ = 76.408 (2)°
V = 1855.00 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.73 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.662, T_max = 0.724
45699 measured reflections
10505 independent reflections
7252 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.01
10505 reflections
407 parameters
H-atom parameters constrained
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.606 (3)	147
O2—H2A⋯N2	0.82	1.91	2.617 (3)	143
C16—H16A⋯Cg2ⁱ	0.96	2.91	3.785 (5)	153
Symmetry code: (i) x-1, y, z.

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/S1600536812023653/rk2360sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023653/rk2360Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023653/rk2360Isup3.cml

checkCIF report

Comment top

Schiff base derivatives exhibit antibacterial, antitumor and antitoxic activities (Santos et al., 2001). The asymmetric unit of the title compound I, (Fig. 1), contains two independent molecules. The geometric parameters in I are comparable with the similar reported structures (Lin et al., 2005; Raja et al., 2008). The dihedral angles between the benzene rings (C1-C6) and (C8-C13) & (C20-C25) and (C27-C32) are 84.26 (17)° and 86.69 (15)°. Further, both molecules adopts anti-periplanar (C1-C7-N1-C8 = 177.2 (2)° and C20-C26-N2-C27 = 175.8 (2)°) conformation about C═N bond.

The molecular structure is stabilized by weak intramolecular O–H···N hydrogen bonds and the crystal structure exhibit weak intermolecular C–H···π (Cg2ⁱ) (Table 1, Fig. 2) and π–π interactions (Cg1···Cg1ⁱⁱ) with distance 3.8622 (18)Å. Cg1 is the centroid of (C1-C6) ring; Cg2 is the centroid of (C8-C13) ring. Symmetry codes: (i) x-1, y, z; (ii) 1-x, 1-y, -z.

Related literature top

For the biological activity of Schiff base ligands, see: Santos et al. (2001). For related strucutures, see: Raja et al. (2008); Lin et al. (2005).

Experimental top

An ethanolic solution (10 ml) of 2,6-diisopropylaniline (2 mmol) was stirred in a round bottom flask followed by drop wise addition of ethanolic solution (10 ml) of 5-iodosalicylaldehyde (2 mmol). The reaction mixture was then refluxed for 3 h and upon cooling to 273 K. A yellow solid precipitate from the reaction mixture was filtered out, washed with ice cold ethanol and dried over anhydrous CaCl₂. Single crystals of good diffraction quality were obtained by the recrystallization of compound from ethanol solution by slow evaporation. Yield: 70 %.

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 title compound with the atom labels. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The intramolecular O–H···N hydrogen bonds and intermolecular C–H···π interaction (dashed lines) in crystal structure of title compound.

2-[(2,6-Diisopropylphenyl)iminomethyl]-4-iodophenol top

Crystal data top

C₁₉H₂₂INO	Z = 4
M_r = 407.28	F(000) = 816
Triclinic, P1	D_x = 1.458 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9891 (2) Å	Cell parameters from 10508 reflections
b = 12.4270 (5) Å	θ = 0.8–29.8°
c = 25.8832 (10) Å	µ = 1.73 mm⁻¹
α = 83.065 (2)°	T = 295 K
β = 84.860 (3)°	Prism, yellow
γ = 76.408 (2)°	0.26 × 0.24 × 0.20 mm
V = 1855.00 (12) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	10505 independent reflections
Radiation source: fine-focus sealed tube	7252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 29.8°, θ_min = 0.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.662, T_max = 0.724	k = −17→17
45699 measured reflections	l = −36→36

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0464P)² + 1.3528P] where P = (F_o² + 2F_c²)/3
10505 reflections	(Δ/σ)_max < 0.001
407 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₁₉H₂₂INO	γ = 76.408 (2)°
M_r = 407.28	V = 1855.00 (12) Å³
Triclinic, P1	Z = 4
a = 5.9891 (2) Å	Mo Kα radiation
b = 12.4270 (5) Å	µ = 1.73 mm⁻¹
c = 25.8832 (10) Å	T = 295 K
α = 83.065 (2)°	0.26 × 0.24 × 0.20 mm
β = 84.860 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	10505 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7252 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.724	R_int = 0.025
45699 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	Δρ_max = 0.91 e Å⁻³
10505 reflections	Δρ_min = −0.65 e Å⁻³
407 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4118 (5)	0.6977 (2)	0.00843 (10)	0.0464 (6)
C2	0.5675 (5)	0.7050 (2)	−0.03417 (10)	0.0522 (6)
H2	0.6832	0.7430	−0.0330	0.063*
C3	0.5509 (6)	0.6561 (3)	−0.07792 (11)	0.0582 (7)
C4	0.3847 (7)	0.5972 (3)	−0.07979 (13)	0.0668 (9)
H4	0.3753	0.5643	−0.1097	0.080*
C5	0.2343 (7)	0.5870 (3)	−0.03797 (14)	0.0685 (9)
H5	0.1248	0.5454	−0.0392	0.082*
C6	0.2420 (5)	0.6380 (2)	0.00656 (11)	0.0544 (7)
C7	0.4231 (5)	0.7547 (2)	0.05361 (10)	0.0475 (6)
H7	0.5400	0.7923	0.0539	0.057*
C8	0.2887 (5)	0.8156 (2)	0.13537 (10)	0.0472 (6)
C9	0.4337 (6)	0.7673 (3)	0.17544 (11)	0.0563 (7)
C10	0.4269 (7)	0.8276 (3)	0.21734 (12)	0.0748 (10)
H10	0.5214	0.7975	0.2445	0.090*
C11	0.2842 (8)	0.9303 (4)	0.21954 (14)	0.0866 (12)
H11	0.2825	0.9695	0.2481	0.104*
C12	0.1436 (7)	0.9759 (3)	0.17999 (15)	0.0774 (10)
H12	0.0490	1.0465	0.1819	0.093*
C13	0.1385 (5)	0.9198 (3)	0.13727 (12)	0.0572 (7)
C14	−0.0175 (6)	0.9713 (3)	0.09377 (16)	0.0722 (9)
H14	−0.0246	0.9119	0.0727	0.087*
C15	0.0816 (9)	1.0567 (4)	0.05887 (18)	0.1021 (15)
H15A	0.0918	1.1159	0.0786	0.153*
H15B	−0.0162	1.0862	0.0307	0.153*
H15C	0.2324	1.0225	0.0451	0.153*
C16	−0.2637 (8)	1.0227 (5)	0.1132 (2)	0.1217 (19)
H16A	−0.3289	0.9666	0.1336	0.183*
H16B	−0.3546	1.0528	0.0839	0.183*
H16C	−0.2623	1.0811	0.1342	0.183*
C17	0.5924 (6)	0.6533 (3)	0.17394 (12)	0.0661 (8)
H17	0.5806	0.6279	0.1401	0.079*
C18	0.5224 (10)	0.5710 (4)	0.2152 (2)	0.123 (2)
H18A	0.5301	0.5942	0.2489	0.184*
H18B	0.6244	0.4993	0.2125	0.184*
H18C	0.3678	0.5662	0.2107	0.184*
C19	0.8408 (9)	0.6554 (6)	0.1781 (3)	0.159 (3)
H19A	0.8810	0.7129	0.1533	0.239*
H19B	0.9373	0.5847	0.1710	0.239*
H19C	0.8621	0.6701	0.2127	0.239*
C20	0.7450 (4)	0.6051 (2)	0.36056 (10)	0.0411 (5)
C21	0.9503 (5)	0.6272 (2)	0.33716 (12)	0.0531 (7)
C22	0.9664 (6)	0.7363 (3)	0.32285 (15)	0.0663 (9)
H22	1.1011	0.7511	0.3059	0.080*
C23	0.7852 (6)	0.8224 (2)	0.33351 (13)	0.0601 (8)
H23	0.7989	0.8954	0.3244	0.072*
C24	0.5821 (5)	0.8019 (2)	0.35772 (11)	0.0474 (6)
C25	0.5625 (5)	0.6937 (2)	0.37041 (10)	0.0460 (6)
H25	0.4245	0.6796	0.3859	0.055*
C26	0.7213 (4)	0.4913 (2)	0.37687 (10)	0.0427 (5)
H26	0.5809	0.4800	0.3920	0.051*
C27	0.8554 (4)	0.2998 (2)	0.39095 (10)	0.0421 (5)
C28	0.7612 (5)	0.2388 (2)	0.36035 (11)	0.0510 (6)
C29	0.7379 (6)	0.1340 (2)	0.38151 (14)	0.0651 (8)
H29	0.6760	0.0914	0.3620	0.078*
C30	0.8036 (6)	0.0917 (2)	0.43042 (15)	0.0694 (9)
H30	0.7819	0.0220	0.4442	0.083*
C31	0.9005 (6)	0.1515 (3)	0.45893 (14)	0.0660 (8)
H31	0.9477	0.1212	0.4919	0.079*
C32	0.9307 (5)	0.2568 (2)	0.43996 (11)	0.0496 (6)
C33	1.0355 (6)	0.3225 (3)	0.47292 (13)	0.0663 (8)
H33	1.0681	0.3866	0.4501	0.080*
C34	0.8713 (10)	0.3675 (5)	0.5157 (2)	0.1163 (18)
H34A	0.7312	0.4102	0.5014	0.174*
H34B	0.9379	0.4144	0.5337	0.174*
H34C	0.8387	0.3071	0.5397	0.174*
C35	1.2620 (10)	0.2569 (6)	0.4929 (3)	0.160 (3)
H35A	1.3437	0.3068	0.5042	0.240*
H35B	1.3523	0.2178	0.4656	0.240*
H35C	1.2339	0.2044	0.5217	0.240*
C36	0.6849 (7)	0.2835 (3)	0.30611 (12)	0.0674 (9)
H36	0.6893	0.3624	0.3008	0.081*
C37	0.8456 (9)	0.2258 (7)	0.26518 (19)	0.157 (3)
H37A	0.8594	0.1469	0.2719	0.236*
H37B	0.9942	0.2421	0.2658	0.236*
H37C	0.7864	0.2514	0.2315	0.236*
C38	0.4445 (8)	0.2758 (6)	0.29912 (19)	0.121 (2)
H38A	0.4439	0.2012	0.2931	0.181*
H38B	0.3860	0.3262	0.2698	0.181*
H38C	0.3492	0.2952	0.3300	0.181*
I1	0.77120 (5)	0.67673 (3)	−0.144206 (9)	0.09004 (11)
I2	0.31035 (4)	0.932551 (16)	0.377683 (10)	0.06823 (9)
N1	0.2794 (4)	0.75482 (19)	0.09260 (8)	0.0477 (5)
N2	0.8848 (4)	0.40812 (18)	0.37106 (9)	0.0449 (5)
O1	0.0845 (5)	0.6295 (2)	0.04618 (9)	0.0760 (7)
H1	0.1016	0.6665	0.0691	0.114*
O2	1.1358 (4)	0.54504 (19)	0.32778 (13)	0.0823 (8)
H2A	1.0987	0.4850	0.3325	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0554 (15)	0.0450 (14)	0.0400 (13)	−0.0130 (11)	−0.0087 (11)	−0.0022 (11)
C2	0.0640 (17)	0.0561 (16)	0.0394 (14)	−0.0191 (13)	−0.0049 (12)	−0.0041 (12)
C3	0.0696 (19)	0.0612 (18)	0.0408 (15)	−0.0069 (14)	−0.0054 (13)	−0.0080 (13)
C4	0.088 (2)	0.0637 (19)	0.0531 (18)	−0.0144 (17)	−0.0161 (17)	−0.0193 (15)
C5	0.083 (2)	0.068 (2)	0.066 (2)	−0.0317 (18)	−0.0164 (17)	−0.0153 (16)
C6	0.0649 (18)	0.0553 (16)	0.0476 (15)	−0.0216 (13)	−0.0102 (13)	−0.0029 (13)
C7	0.0572 (15)	0.0515 (15)	0.0386 (13)	−0.0212 (12)	−0.0055 (11)	−0.0040 (11)
C8	0.0554 (15)	0.0534 (15)	0.0355 (13)	−0.0209 (12)	0.0057 (11)	−0.0041 (11)
C9	0.0730 (19)	0.0602 (17)	0.0371 (14)	−0.0198 (15)	−0.0017 (13)	−0.0028 (12)
C10	0.104 (3)	0.083 (2)	0.0395 (16)	−0.022 (2)	−0.0094 (17)	−0.0111 (16)
C11	0.127 (4)	0.087 (3)	0.0495 (19)	−0.024 (3)	0.004 (2)	−0.0308 (19)
C12	0.096 (3)	0.066 (2)	0.067 (2)	−0.0123 (19)	0.009 (2)	−0.0187 (18)
C13	0.0635 (18)	0.0572 (17)	0.0516 (16)	−0.0179 (14)	0.0029 (13)	−0.0052 (13)
C14	0.068 (2)	0.062 (2)	0.084 (3)	−0.0083 (16)	−0.0141 (18)	−0.0043 (18)
C15	0.120 (4)	0.115 (4)	0.074 (3)	−0.045 (3)	−0.021 (3)	0.023 (3)
C16	0.073 (3)	0.126 (4)	0.149 (5)	−0.005 (3)	−0.009 (3)	0.019 (4)
C17	0.088 (2)	0.067 (2)	0.0421 (16)	−0.0137 (17)	−0.0141 (15)	−0.0018 (14)
C18	0.109 (4)	0.080 (3)	0.154 (5)	−0.008 (3)	0.025 (3)	0.033 (3)
C19	0.077 (3)	0.127 (5)	0.268 (9)	−0.019 (3)	0.047 (4)	−0.042 (5)
C20	0.0485 (13)	0.0399 (12)	0.0379 (12)	−0.0158 (10)	−0.0037 (10)	−0.0031 (10)
C21	0.0511 (15)	0.0474 (15)	0.0624 (18)	−0.0163 (12)	0.0034 (13)	−0.0066 (13)
C22	0.0600 (18)	0.0577 (18)	0.086 (2)	−0.0314 (15)	0.0084 (16)	0.0003 (16)
C23	0.0695 (19)	0.0413 (14)	0.075 (2)	−0.0264 (14)	−0.0055 (16)	0.0005 (14)
C24	0.0574 (15)	0.0394 (13)	0.0479 (15)	−0.0134 (11)	−0.0074 (12)	−0.0060 (11)
C25	0.0508 (14)	0.0412 (13)	0.0471 (14)	−0.0151 (11)	0.0001 (11)	−0.0030 (11)
C26	0.0472 (13)	0.0404 (13)	0.0423 (13)	−0.0152 (10)	0.0023 (10)	−0.0047 (10)
C27	0.0436 (13)	0.0358 (12)	0.0443 (14)	−0.0053 (10)	0.0024 (10)	−0.0053 (10)
C28	0.0642 (17)	0.0393 (13)	0.0507 (16)	−0.0123 (12)	−0.0058 (13)	−0.0067 (11)
C29	0.086 (2)	0.0378 (14)	0.075 (2)	−0.0168 (14)	−0.0072 (17)	−0.0114 (14)
C30	0.087 (2)	0.0340 (14)	0.082 (2)	−0.0088 (14)	−0.0054 (19)	0.0071 (15)
C31	0.073 (2)	0.0535 (17)	0.063 (2)	−0.0055 (15)	−0.0123 (16)	0.0161 (15)
C32	0.0494 (14)	0.0513 (15)	0.0453 (15)	−0.0071 (12)	−0.0018 (11)	−0.0027 (12)
C33	0.072 (2)	0.081 (2)	0.0519 (17)	−0.0277 (17)	−0.0118 (15)	−0.0035 (16)
C34	0.127 (4)	0.136 (4)	0.105 (4)	−0.054 (3)	0.027 (3)	−0.065 (3)
C35	0.106 (4)	0.204 (7)	0.181 (7)	0.002 (4)	−0.072 (4)	−0.085 (6)
C36	0.104 (3)	0.0578 (18)	0.0497 (17)	−0.0327 (18)	−0.0160 (17)	−0.0044 (14)
C37	0.084 (3)	0.300 (10)	0.063 (3)	−0.001 (4)	0.005 (2)	−0.019 (4)
C38	0.077 (3)	0.182 (6)	0.081 (3)	0.007 (3)	−0.018 (2)	0.014 (3)
I1	0.1026 (2)	0.1210 (2)	0.04660 (13)	−0.02447 (17)	0.00854 (12)	−0.02049 (13)
I2	0.07654 (15)	0.04092 (11)	0.08644 (17)	−0.00987 (9)	−0.00392 (11)	−0.01118 (10)
N1	0.0552 (13)	0.0516 (13)	0.0394 (11)	−0.0199 (10)	0.0001 (10)	−0.0041 (10)
N2	0.0503 (12)	0.0404 (11)	0.0451 (12)	−0.0140 (9)	0.0022 (9)	−0.0058 (9)
O1	0.0842 (16)	0.0992 (19)	0.0619 (14)	−0.0542 (15)	0.0054 (12)	−0.0181 (13)
O2	0.0569 (13)	0.0544 (13)	0.131 (2)	−0.0179 (10)	0.0303 (14)	−0.0085 (14)

Geometric parameters (Å, º) top

C1—C2	1.388 (4)	C20—C21	1.393 (4)
C1—C6	1.400 (4)	C20—C26	1.462 (3)
C1—C7	1.452 (4)	C21—O2	1.347 (4)
C2—C3	1.370 (4)	C21—C22	1.385 (4)
C2—H2	0.9300	C22—C23	1.367 (5)
C3—C4	1.373 (5)	C22—H22	0.9300
C3—I1	2.097 (3)	C23—C24	1.382 (4)
C4—C5	1.358 (5)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.375 (4)
C5—C6	1.390 (4)	C24—I2	2.089 (3)
C5—H5	0.9300	C25—H25	0.9300
C6—O1	1.342 (4)	C26—N2	1.259 (3)
C7—N1	1.266 (3)	C26—H26	0.9300
C7—H7	0.9300	C27—C32	1.387 (4)
C8—C13	1.396 (4)	C27—C28	1.396 (4)
C8—C9	1.398 (4)	C27—N2	1.427 (3)
C8—N1	1.425 (3)	C28—C29	1.383 (4)
C9—C10	1.383 (4)	C28—C36	1.515 (4)
C9—C17	1.512 (5)	C29—C30	1.366 (5)
C10—C11	1.363 (6)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.359 (5)
C11—C12	1.367 (6)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.387 (4)
C12—C13	1.383 (5)	C31—H31	0.9300
C12—H12	0.9300	C32—C33	1.515 (4)
C13—C14	1.511 (5)	C33—C34	1.483 (6)
C14—C15	1.504 (6)	C33—C35	1.509 (6)
C14—C16	1.529 (6)	C33—H33	0.9800
C14—H14	0.9800	C34—H34A	0.9600
C15—H15A	0.9600	C34—H34B	0.9600
C15—H15B	0.9600	C34—H34C	0.9600
C15—H15C	0.9600	C35—H35A	0.9600
C16—H16A	0.9600	C35—H35B	0.9600
C16—H16B	0.9600	C35—H35C	0.9600
C16—H16C	0.9600	C36—C38	1.493 (6)
C17—C18	1.490 (6)	C36—C37	1.496 (7)
C17—C19	1.508 (7)	C36—H36	0.9800
C17—H17	0.9800	C37—H37A	0.9600
C18—H18A	0.9600	C37—H37B	0.9600
C18—H18B	0.9600	C37—H37C	0.9600
C18—H18C	0.9600	C38—H38A	0.9600
C19—H19A	0.9600	C38—H38B	0.9600
C19—H19B	0.9600	C38—H38C	0.9600
C19—H19C	0.9600	O1—H1	0.8200
C20—C25	1.387 (4)	O2—H2A	0.8200

C2—C1—C6	119.3 (3)	C21—C20—C26	121.5 (2)
C2—C1—C7	119.6 (2)	O2—C21—C22	118.5 (3)
C6—C1—C7	121.0 (3)	O2—C21—C20	121.8 (3)
C3—C2—C1	120.0 (3)	C22—C21—C20	119.7 (3)
C3—C2—H2	120.0	C23—C22—C21	120.4 (3)
C1—C2—H2	120.0	C23—C22—H22	119.8
C2—C3—C4	120.8 (3)	C21—C22—H22	119.8
C2—C3—I1	119.9 (2)	C22—C23—C24	120.6 (3)
C4—C3—I1	119.3 (2)	C22—C23—H23	119.7
C5—C4—C3	120.0 (3)	C24—C23—H23	119.7
C5—C4—H4	120.0	C25—C24—C23	119.3 (3)
C3—C4—H4	120.0	C25—C24—I2	119.8 (2)
C4—C5—C6	120.8 (3)	C23—C24—I2	120.9 (2)
C4—C5—H5	119.6	C24—C25—C20	121.1 (3)
C6—C5—H5	119.6	C24—C25—H25	119.4
O1—C6—C5	118.9 (3)	C20—C25—H25	119.4
O1—C6—C1	122.1 (3)	N2—C26—C20	122.2 (2)
C5—C6—C1	119.0 (3)	N2—C26—H26	118.9
N1—C7—C1	122.3 (2)	C20—C26—H26	118.9
N1—C7—H7	118.9	C32—C27—C28	122.0 (2)
C1—C7—H7	118.9	C32—C27—N2	118.2 (2)
C13—C8—C9	122.1 (3)	C28—C27—N2	119.8 (2)
C13—C8—N1	117.8 (3)	C29—C28—C27	117.3 (3)
C9—C8—N1	120.0 (3)	C29—C28—C36	120.2 (3)
C10—C9—C8	117.6 (3)	C27—C28—C36	122.5 (2)
C10—C9—C17	120.4 (3)	C30—C29—C28	121.6 (3)
C8—C9—C17	122.0 (3)	C30—C29—H29	119.2
C11—C10—C9	121.3 (3)	C28—C29—H29	119.2
C11—C10—H10	119.4	C31—C30—C29	120.0 (3)
C9—C10—H10	119.4	C31—C30—H30	120.0
C10—C11—C12	120.3 (3)	C29—C30—H30	120.0
C10—C11—H11	119.9	C30—C31—C32	121.4 (3)
C12—C11—H11	119.9	C30—C31—H31	119.3
C11—C12—C13	121.7 (4)	C32—C31—H31	119.3
C11—C12—H12	119.2	C27—C32—C31	117.6 (3)
C13—C12—H12	119.2	C27—C32—C33	121.9 (3)
C12—C13—C8	117.1 (3)	C31—C32—C33	120.4 (3)
C12—C13—C14	121.1 (3)	C34—C33—C35	111.9 (4)
C8—C13—C14	121.7 (3)	C34—C33—C32	111.7 (3)
C15—C14—C13	110.6 (3)	C35—C33—C32	112.3 (4)
C15—C14—C16	110.0 (4)	C34—C33—H33	106.8
C13—C14—C16	113.4 (4)	C35—C33—H33	106.8
C15—C14—H14	107.5	C32—C33—H33	106.8
C13—C14—H14	107.5	C33—C34—H34A	109.5
C16—C14—H14	107.5	C33—C34—H34B	109.5
C14—C15—H15A	109.5	H34A—C34—H34B	109.5
C14—C15—H15B	109.5	C33—C34—H34C	109.5
H15A—C15—H15B	109.5	H34A—C34—H34C	109.5
C14—C15—H15C	109.5	H34B—C34—H34C	109.5
H15A—C15—H15C	109.5	C33—C35—H35A	109.5
H15B—C15—H15C	109.5	C33—C35—H35B	109.5
C14—C16—H16A	109.5	H35A—C35—H35B	109.5
C14—C16—H16B	109.5	C33—C35—H35C	109.5
H16A—C16—H16B	109.5	H35A—C35—H35C	109.5
C14—C16—H16C	109.5	H35B—C35—H35C	109.5
H16A—C16—H16C	109.5	C38—C36—C37	109.8 (4)
H16B—C16—H16C	109.5	C38—C36—C28	112.7 (3)
C18—C17—C19	110.0 (4)	C37—C36—C28	111.3 (4)
C18—C17—C9	111.8 (3)	C38—C36—H36	107.6
C19—C17—C9	112.4 (4)	C37—C36—H36	107.6
C18—C17—H17	107.5	C28—C36—H36	107.6
C19—C17—H17	107.5	C36—C37—H37A	109.5
C9—C17—H17	107.5	C36—C37—H37B	109.5
C17—C18—H18A	109.5	H37A—C37—H37B	109.5
C17—C18—H18B	109.5	C36—C37—H37C	109.5
H18A—C18—H18B	109.5	H37A—C37—H37C	109.5
C17—C18—H18C	109.5	H37B—C37—H37C	109.5
H18A—C18—H18C	109.5	C36—C38—H38A	109.5
H18B—C18—H18C	109.5	C36—C38—H38B	109.5
C17—C19—H19A	109.5	H38A—C38—H38B	109.5
C17—C19—H19B	109.5	C36—C38—H38C	109.5
H19A—C19—H19B	109.5	H38A—C38—H38C	109.5
C17—C19—H19C	109.5	H38B—C38—H38C	109.5
H19A—C19—H19C	109.5	C7—N1—C8	121.0 (2)
H19B—C19—H19C	109.5	C26—N2—C27	119.4 (2)
C25—C20—C21	118.9 (2)	C6—O1—H1	109.5
C25—C20—C26	119.5 (2)	C21—O2—H2A	109.5

C6—C1—C2—C3	1.5 (4)	C26—C20—C21—C22	−179.2 (3)
C7—C1—C2—C3	−176.8 (3)	O2—C21—C22—C23	−177.4 (3)
C1—C2—C3—C4	−1.7 (5)	C20—C21—C22—C23	2.7 (5)
C1—C2—C3—I1	175.6 (2)	C21—C22—C23—C24	−1.3 (5)
C2—C3—C4—C5	0.1 (5)	C22—C23—C24—C25	−0.9 (5)
I1—C3—C4—C5	−177.2 (3)	C22—C23—C24—I2	176.8 (3)
C3—C4—C5—C6	1.7 (5)	C23—C24—C25—C20	1.7 (4)
C4—C5—C6—O1	177.4 (3)	I2—C24—C25—C20	−176.0 (2)
C4—C5—C6—C1	−1.8 (5)	C21—C20—C25—C24	−0.3 (4)
C2—C1—C6—O1	−179.0 (3)	C26—C20—C25—C24	177.1 (2)
C7—C1—C6—O1	−0.7 (5)	C25—C20—C26—N2	−176.7 (3)
C2—C1—C6—C5	0.2 (4)	C21—C20—C26—N2	0.6 (4)
C7—C1—C6—C5	178.5 (3)	C32—C27—C28—C29	2.1 (4)
C2—C1—C7—N1	176.9 (3)	N2—C27—C28—C29	179.7 (3)
C6—C1—C7—N1	−1.3 (4)	C32—C27—C28—C36	−178.1 (3)
C13—C8—C9—C10	−1.1 (5)	N2—C27—C28—C36	−0.6 (4)
N1—C8—C9—C10	−176.6 (3)	C27—C28—C29—C30	0.2 (5)
C13—C8—C9—C17	178.6 (3)	C36—C28—C29—C30	−179.5 (3)
N1—C8—C9—C17	3.0 (4)	C28—C29—C30—C31	−1.9 (6)
C8—C9—C10—C11	0.0 (6)	C29—C30—C31—C32	1.4 (6)
C17—C9—C10—C11	−179.7 (4)	C28—C27—C32—C31	−2.6 (4)
C9—C10—C11—C12	0.1 (7)	N2—C27—C32—C31	179.8 (3)
C10—C11—C12—C13	0.9 (7)	C28—C27—C32—C33	179.3 (3)
C11—C12—C13—C8	−2.0 (6)	N2—C27—C32—C33	1.7 (4)
C11—C12—C13—C14	−179.9 (4)	C30—C31—C32—C27	0.8 (5)
C9—C8—C13—C12	2.1 (5)	C30—C31—C32—C33	178.9 (3)
N1—C8—C13—C12	177.7 (3)	C27—C32—C33—C34	103.9 (4)
C9—C8—C13—C14	180.0 (3)	C31—C32—C33—C34	−74.2 (5)
N1—C8—C13—C14	−4.4 (4)	C27—C32—C33—C35	−129.4 (5)
C12—C13—C14—C15	77.3 (5)	C31—C32—C33—C35	52.5 (5)
C8—C13—C14—C15	−100.5 (4)	C29—C28—C36—C38	51.6 (5)
C12—C13—C14—C16	−46.8 (5)	C27—C28—C36—C38	−128.2 (4)
C8—C13—C14—C16	135.3 (4)	C29—C28—C36—C37	−72.3 (5)
C10—C9—C17—C18	66.9 (5)	C27—C28—C36—C37	107.9 (5)
C8—C9—C17—C18	−112.8 (4)	C1—C7—N1—C8	−177.2 (3)
C10—C9—C17—C19	−57.3 (5)	C13—C8—N1—C7	99.1 (3)
C8—C9—C17—C19	123.0 (5)	C9—C8—N1—C7	−85.2 (3)
C25—C20—C21—O2	178.3 (3)	C20—C26—N2—C27	175.8 (2)
C26—C20—C21—O2	0.9 (5)	C32—C27—N2—C26	−95.2 (3)
C25—C20—C21—C22	−1.9 (4)	C28—C27—N2—C26	87.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.606 (3)	147
O2—H2A···N2	0.82	1.91	2.617 (3)	143
C16—H16A···Cg2ⁱ	0.96	2.91	3.785 (5)	153

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂INO
M_r	407.28
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.9891 (2), 12.4270 (5), 25.8832 (10)
α, β, γ (°)	83.065 (2), 84.860 (3), 76.408 (2)
V (Å³)	1855.00 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.73
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.662, 0.724
No. of measured, independent and observed [I > 2σ(I)] reflections	45699, 10505, 7252
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.01
No. of reflections	10505
No. of parameters	407
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.65

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.606 (3)	147
O2—H2A···N2	0.82	1.91	2.617 (3)	143
C16—H16A···Cg2ⁱ	0.96	2.91	3.785 (5)	153

Symmetry code: (i) x−1, y, z.

Acknowledgements

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lin, J., Cui, G.-H., Li, J.-R. & Xu, S.-S. (2005). Acta Cryst. E61, o627–o628. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raja, K. K., Bilal, I. M., Thambidurai, S., Rajagopal, G. & SubbiahPandi, A. (2008). Acta Cryst. E64, o2265. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1915

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