organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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 ππ [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[Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.]). For related strucutures, see: Raja et al. (2008[Raja, K. K., Bilal, I. M., Thambidurai, S., Rajagopal, G. & SubbiahPandi, A. (2008). Acta Cryst. E64, o2265.]); Lin et al. (2005[Lin, J., Cui, G.-H., Li, J.-R. & Xu, S.-S. (2005). Acta Cryst. E61, o627-o628.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22INO

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.662, Tmax = 0.724

  • 45699 measured reflections

  • 10505 independent reflections

  • 7252 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.01

  • 10505 reflections

  • 407 parameters

  • H-atom parameters constrained

  • Δρmax = 0.91 e Å−3

  • Δρmin = −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 DA 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—H16ACg2i 0.96 2.91 3.785 (5) 153
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 CN 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 ππ 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 %.

Refinement top

The H atoms were positioned geometrically with C–H = 0.93-0.98Å and O–H = 0.82Å, and allowed to ride on their parent atoms, with Uiso(H) = 1.5 Ueq(O) (or) 1.2Ueq(C) (or) 1.5Ueq(Cmethyl).

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
[Figure 1] 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.
[Figure 2] 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
C19H22INOZ = 4
Mr = 407.28F(000) = 816
Triclinic, P1Dx = 1.458 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9891 (2) ÅCell parameters from 10508 reflections
b = 12.4270 (5) Åθ = 0.8–29.8°
c = 25.8832 (10) ŵ = 1.73 mm1
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 tube7252 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω and ϕ scansθmax = 29.8°, θmin = 0.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.662, Tmax = 0.724k = 1717
45699 measured reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0464P)2 + 1.3528P]
where P = (Fo2 + 2Fc2)/3
10505 reflections(Δ/σ)max < 0.001
407 parametersΔρmax = 0.91 e Å3
0 restraintsΔρmin = 0.65 e Å3
Crystal data top
C19H22INOγ = 76.408 (2)°
Mr = 407.28V = 1855.00 (12) Å3
Triclinic, P1Z = 4
a = 5.9891 (2) ÅMo Kα radiation
b = 12.4270 (5) ŵ = 1.73 mm1
c = 25.8832 (10) ÅT = 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)
Tmin = 0.662, Tmax = 0.724Rint = 0.025
45699 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.01Δρmax = 0.91 e Å3
10505 reflectionsΔρmin = 0.65 e Å3
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
xyzUiso*/Ueq
C10.4118 (5)0.6977 (2)0.00843 (10)0.0464 (6)
C20.5675 (5)0.7050 (2)0.03417 (10)0.0522 (6)
H20.68320.74300.03300.063*
C30.5509 (6)0.6561 (3)0.07792 (11)0.0582 (7)
C40.3847 (7)0.5972 (3)0.07979 (13)0.0668 (9)
H40.37530.56430.10970.080*
C50.2343 (7)0.5870 (3)0.03797 (14)0.0685 (9)
H50.12480.54540.03920.082*
C60.2420 (5)0.6380 (2)0.00656 (11)0.0544 (7)
C70.4231 (5)0.7547 (2)0.05361 (10)0.0475 (6)
H70.54000.79230.05390.057*
C80.2887 (5)0.8156 (2)0.13537 (10)0.0472 (6)
C90.4337 (6)0.7673 (3)0.17544 (11)0.0563 (7)
C100.4269 (7)0.8276 (3)0.21734 (12)0.0748 (10)
H100.52140.79750.24450.090*
C110.2842 (8)0.9303 (4)0.21954 (14)0.0866 (12)
H110.28250.96950.24810.104*
C120.1436 (7)0.9759 (3)0.17999 (15)0.0774 (10)
H120.04901.04650.18190.093*
C130.1385 (5)0.9198 (3)0.13727 (12)0.0572 (7)
C140.0175 (6)0.9713 (3)0.09377 (16)0.0722 (9)
H140.02460.91190.07270.087*
C150.0816 (9)1.0567 (4)0.05887 (18)0.1021 (15)
H15A0.09181.11590.07860.153*
H15B0.01621.08620.03070.153*
H15C0.23241.02250.04510.153*
C160.2637 (8)1.0227 (5)0.1132 (2)0.1217 (19)
H16A0.32890.96660.13360.183*
H16B0.35461.05280.08390.183*
H16C0.26231.08110.13420.183*
C170.5924 (6)0.6533 (3)0.17394 (12)0.0661 (8)
H170.58060.62790.14010.079*
C180.5224 (10)0.5710 (4)0.2152 (2)0.123 (2)
H18A0.53010.59420.24890.184*
H18B0.62440.49930.21250.184*
H18C0.36780.56620.21070.184*
C190.8408 (9)0.6554 (6)0.1781 (3)0.159 (3)
H19A0.88100.71290.15330.239*
H19B0.93730.58470.17100.239*
H19C0.86210.67010.21270.239*
C200.7450 (4)0.6051 (2)0.36056 (10)0.0411 (5)
C210.9503 (5)0.6272 (2)0.33716 (12)0.0531 (7)
C220.9664 (6)0.7363 (3)0.32285 (15)0.0663 (9)
H221.10110.75110.30590.080*
C230.7852 (6)0.8224 (2)0.33351 (13)0.0601 (8)
H230.79890.89540.32440.072*
C240.5821 (5)0.8019 (2)0.35772 (11)0.0474 (6)
C250.5625 (5)0.6937 (2)0.37041 (10)0.0460 (6)
H250.42450.67960.38590.055*
C260.7213 (4)0.4913 (2)0.37687 (10)0.0427 (5)
H260.58090.48000.39200.051*
C270.8554 (4)0.2998 (2)0.39095 (10)0.0421 (5)
C280.7612 (5)0.2388 (2)0.36035 (11)0.0510 (6)
C290.7379 (6)0.1340 (2)0.38151 (14)0.0651 (8)
H290.67600.09140.36200.078*
C300.8036 (6)0.0917 (2)0.43042 (15)0.0694 (9)
H300.78190.02200.44420.083*
C310.9005 (6)0.1515 (3)0.45893 (14)0.0660 (8)
H310.94770.12120.49190.079*
C320.9307 (5)0.2568 (2)0.43996 (11)0.0496 (6)
C331.0355 (6)0.3225 (3)0.47292 (13)0.0663 (8)
H331.06810.38660.45010.080*
C340.8713 (10)0.3675 (5)0.5157 (2)0.1163 (18)
H34A0.73120.41020.50140.174*
H34B0.93790.41440.53370.174*
H34C0.83870.30710.53970.174*
C351.2620 (10)0.2569 (6)0.4929 (3)0.160 (3)
H35A1.34370.30680.50420.240*
H35B1.35230.21780.46560.240*
H35C1.23390.20440.52170.240*
C360.6849 (7)0.2835 (3)0.30611 (12)0.0674 (9)
H360.68930.36240.30080.081*
C370.8456 (9)0.2258 (7)0.26518 (19)0.157 (3)
H37A0.85940.14690.27190.236*
H37B0.99420.24210.26580.236*
H37C0.78640.25140.23150.236*
C380.4445 (8)0.2758 (6)0.29912 (19)0.121 (2)
H38A0.44390.20120.29310.181*
H38B0.38600.32620.26980.181*
H38C0.34920.29520.33000.181*
I10.77120 (5)0.67673 (3)0.144206 (9)0.09004 (11)
I20.31035 (4)0.932551 (16)0.377683 (10)0.06823 (9)
N10.2794 (4)0.75482 (19)0.09260 (8)0.0477 (5)
N20.8848 (4)0.40812 (18)0.37106 (9)0.0449 (5)
O10.0845 (5)0.6295 (2)0.04618 (9)0.0760 (7)
H10.10160.66650.06910.114*
O21.1358 (4)0.54504 (19)0.32778 (13)0.0823 (8)
H2A1.09870.48500.33250.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0554 (15)0.0450 (14)0.0400 (13)0.0130 (11)0.0087 (11)0.0022 (11)
C20.0640 (17)0.0561 (16)0.0394 (14)0.0191 (13)0.0049 (12)0.0041 (12)
C30.0696 (19)0.0612 (18)0.0408 (15)0.0069 (14)0.0054 (13)0.0080 (13)
C40.088 (2)0.0637 (19)0.0531 (18)0.0144 (17)0.0161 (17)0.0193 (15)
C50.083 (2)0.068 (2)0.066 (2)0.0317 (18)0.0164 (17)0.0153 (16)
C60.0649 (18)0.0553 (16)0.0476 (15)0.0216 (13)0.0102 (13)0.0029 (13)
C70.0572 (15)0.0515 (15)0.0386 (13)0.0212 (12)0.0055 (11)0.0040 (11)
C80.0554 (15)0.0534 (15)0.0355 (13)0.0209 (12)0.0057 (11)0.0041 (11)
C90.0730 (19)0.0602 (17)0.0371 (14)0.0198 (15)0.0017 (13)0.0028 (12)
C100.104 (3)0.083 (2)0.0395 (16)0.022 (2)0.0094 (17)0.0111 (16)
C110.127 (4)0.087 (3)0.0495 (19)0.024 (3)0.004 (2)0.0308 (19)
C120.096 (3)0.066 (2)0.067 (2)0.0123 (19)0.009 (2)0.0187 (18)
C130.0635 (18)0.0572 (17)0.0516 (16)0.0179 (14)0.0029 (13)0.0052 (13)
C140.068 (2)0.062 (2)0.084 (3)0.0083 (16)0.0141 (18)0.0043 (18)
C150.120 (4)0.115 (4)0.074 (3)0.045 (3)0.021 (3)0.023 (3)
C160.073 (3)0.126 (4)0.149 (5)0.005 (3)0.009 (3)0.019 (4)
C170.088 (2)0.067 (2)0.0421 (16)0.0137 (17)0.0141 (15)0.0018 (14)
C180.109 (4)0.080 (3)0.154 (5)0.008 (3)0.025 (3)0.033 (3)
C190.077 (3)0.127 (5)0.268 (9)0.019 (3)0.047 (4)0.042 (5)
C200.0485 (13)0.0399 (12)0.0379 (12)0.0158 (10)0.0037 (10)0.0031 (10)
C210.0511 (15)0.0474 (15)0.0624 (18)0.0163 (12)0.0034 (13)0.0066 (13)
C220.0600 (18)0.0577 (18)0.086 (2)0.0314 (15)0.0084 (16)0.0003 (16)
C230.0695 (19)0.0413 (14)0.075 (2)0.0264 (14)0.0055 (16)0.0005 (14)
C240.0574 (15)0.0394 (13)0.0479 (15)0.0134 (11)0.0074 (12)0.0060 (11)
C250.0508 (14)0.0412 (13)0.0471 (14)0.0151 (11)0.0001 (11)0.0030 (11)
C260.0472 (13)0.0404 (13)0.0423 (13)0.0152 (10)0.0023 (10)0.0047 (10)
C270.0436 (13)0.0358 (12)0.0443 (14)0.0053 (10)0.0024 (10)0.0053 (10)
C280.0642 (17)0.0393 (13)0.0507 (16)0.0123 (12)0.0058 (13)0.0067 (11)
C290.086 (2)0.0378 (14)0.075 (2)0.0168 (14)0.0072 (17)0.0114 (14)
C300.087 (2)0.0340 (14)0.082 (2)0.0088 (14)0.0054 (19)0.0071 (15)
C310.073 (2)0.0535 (17)0.063 (2)0.0055 (15)0.0123 (16)0.0161 (15)
C320.0494 (14)0.0513 (15)0.0453 (15)0.0071 (12)0.0018 (11)0.0027 (12)
C330.072 (2)0.081 (2)0.0519 (17)0.0277 (17)0.0118 (15)0.0035 (16)
C340.127 (4)0.136 (4)0.105 (4)0.054 (3)0.027 (3)0.065 (3)
C350.106 (4)0.204 (7)0.181 (7)0.002 (4)0.072 (4)0.085 (6)
C360.104 (3)0.0578 (18)0.0497 (17)0.0327 (18)0.0160 (17)0.0044 (14)
C370.084 (3)0.300 (10)0.063 (3)0.001 (4)0.005 (2)0.019 (4)
C380.077 (3)0.182 (6)0.081 (3)0.007 (3)0.018 (2)0.014 (3)
I10.1026 (2)0.1210 (2)0.04660 (13)0.02447 (17)0.00854 (12)0.02049 (13)
I20.07654 (15)0.04092 (11)0.08644 (17)0.00987 (9)0.00392 (11)0.01118 (10)
N10.0552 (13)0.0516 (13)0.0394 (11)0.0199 (10)0.0001 (10)0.0041 (10)
N20.0503 (12)0.0404 (11)0.0451 (12)0.0140 (9)0.0022 (9)0.0058 (9)
O10.0842 (16)0.0992 (19)0.0619 (14)0.0542 (15)0.0054 (12)0.0181 (13)
O20.0569 (13)0.0544 (13)0.131 (2)0.0179 (10)0.0303 (14)0.0085 (14)
Geometric parameters (Å, º) top
C1—C21.388 (4)C20—C211.393 (4)
C1—C61.400 (4)C20—C261.462 (3)
C1—C71.452 (4)C21—O21.347 (4)
C2—C31.370 (4)C21—C221.385 (4)
C2—H20.9300C22—C231.367 (5)
C3—C41.373 (5)C22—H220.9300
C3—I12.097 (3)C23—C241.382 (4)
C4—C51.358 (5)C23—H230.9300
C4—H40.9300C24—C251.375 (4)
C5—C61.390 (4)C24—I22.089 (3)
C5—H50.9300C25—H250.9300
C6—O11.342 (4)C26—N21.259 (3)
C7—N11.266 (3)C26—H260.9300
C7—H70.9300C27—C321.387 (4)
C8—C131.396 (4)C27—C281.396 (4)
C8—C91.398 (4)C27—N21.427 (3)
C8—N11.425 (3)C28—C291.383 (4)
C9—C101.383 (4)C28—C361.515 (4)
C9—C171.512 (5)C29—C301.366 (5)
C10—C111.363 (6)C29—H290.9300
C10—H100.9300C30—C311.359 (5)
C11—C121.367 (6)C30—H300.9300
C11—H110.9300C31—C321.387 (4)
C12—C131.383 (5)C31—H310.9300
C12—H120.9300C32—C331.515 (4)
C13—C141.511 (5)C33—C341.483 (6)
C14—C151.504 (6)C33—C351.509 (6)
C14—C161.529 (6)C33—H330.9800
C14—H140.9800C34—H34A0.9600
C15—H15A0.9600C34—H34B0.9600
C15—H15B0.9600C34—H34C0.9600
C15—H15C0.9600C35—H35A0.9600
C16—H16A0.9600C35—H35B0.9600
C16—H16B0.9600C35—H35C0.9600
C16—H16C0.9600C36—C381.493 (6)
C17—C181.490 (6)C36—C371.496 (7)
C17—C191.508 (7)C36—H360.9800
C17—H170.9800C37—H37A0.9600
C18—H18A0.9600C37—H37B0.9600
C18—H18B0.9600C37—H37C0.9600
C18—H18C0.9600C38—H38A0.9600
C19—H19A0.9600C38—H38B0.9600
C19—H19B0.9600C38—H38C0.9600
C19—H19C0.9600O1—H10.8200
C20—C251.387 (4)O2—H2A0.8200
C2—C1—C6119.3 (3)C21—C20—C26121.5 (2)
C2—C1—C7119.6 (2)O2—C21—C22118.5 (3)
C6—C1—C7121.0 (3)O2—C21—C20121.8 (3)
C3—C2—C1120.0 (3)C22—C21—C20119.7 (3)
C3—C2—H2120.0C23—C22—C21120.4 (3)
C1—C2—H2120.0C23—C22—H22119.8
C2—C3—C4120.8 (3)C21—C22—H22119.8
C2—C3—I1119.9 (2)C22—C23—C24120.6 (3)
C4—C3—I1119.3 (2)C22—C23—H23119.7
C5—C4—C3120.0 (3)C24—C23—H23119.7
C5—C4—H4120.0C25—C24—C23119.3 (3)
C3—C4—H4120.0C25—C24—I2119.8 (2)
C4—C5—C6120.8 (3)C23—C24—I2120.9 (2)
C4—C5—H5119.6C24—C25—C20121.1 (3)
C6—C5—H5119.6C24—C25—H25119.4
O1—C6—C5118.9 (3)C20—C25—H25119.4
O1—C6—C1122.1 (3)N2—C26—C20122.2 (2)
C5—C6—C1119.0 (3)N2—C26—H26118.9
N1—C7—C1122.3 (2)C20—C26—H26118.9
N1—C7—H7118.9C32—C27—C28122.0 (2)
C1—C7—H7118.9C32—C27—N2118.2 (2)
C13—C8—C9122.1 (3)C28—C27—N2119.8 (2)
C13—C8—N1117.8 (3)C29—C28—C27117.3 (3)
C9—C8—N1120.0 (3)C29—C28—C36120.2 (3)
C10—C9—C8117.6 (3)C27—C28—C36122.5 (2)
C10—C9—C17120.4 (3)C30—C29—C28121.6 (3)
C8—C9—C17122.0 (3)C30—C29—H29119.2
C11—C10—C9121.3 (3)C28—C29—H29119.2
C11—C10—H10119.4C31—C30—C29120.0 (3)
C9—C10—H10119.4C31—C30—H30120.0
C10—C11—C12120.3 (3)C29—C30—H30120.0
C10—C11—H11119.9C30—C31—C32121.4 (3)
C12—C11—H11119.9C30—C31—H31119.3
C11—C12—C13121.7 (4)C32—C31—H31119.3
C11—C12—H12119.2C27—C32—C31117.6 (3)
C13—C12—H12119.2C27—C32—C33121.9 (3)
C12—C13—C8117.1 (3)C31—C32—C33120.4 (3)
C12—C13—C14121.1 (3)C34—C33—C35111.9 (4)
C8—C13—C14121.7 (3)C34—C33—C32111.7 (3)
C15—C14—C13110.6 (3)C35—C33—C32112.3 (4)
C15—C14—C16110.0 (4)C34—C33—H33106.8
C13—C14—C16113.4 (4)C35—C33—H33106.8
C15—C14—H14107.5C32—C33—H33106.8
C13—C14—H14107.5C33—C34—H34A109.5
C16—C14—H14107.5C33—C34—H34B109.5
C14—C15—H15A109.5H34A—C34—H34B109.5
C14—C15—H15B109.5C33—C34—H34C109.5
H15A—C15—H15B109.5H34A—C34—H34C109.5
C14—C15—H15C109.5H34B—C34—H34C109.5
H15A—C15—H15C109.5C33—C35—H35A109.5
H15B—C15—H15C109.5C33—C35—H35B109.5
C14—C16—H16A109.5H35A—C35—H35B109.5
C14—C16—H16B109.5C33—C35—H35C109.5
H16A—C16—H16B109.5H35A—C35—H35C109.5
C14—C16—H16C109.5H35B—C35—H35C109.5
H16A—C16—H16C109.5C38—C36—C37109.8 (4)
H16B—C16—H16C109.5C38—C36—C28112.7 (3)
C18—C17—C19110.0 (4)C37—C36—C28111.3 (4)
C18—C17—C9111.8 (3)C38—C36—H36107.6
C19—C17—C9112.4 (4)C37—C36—H36107.6
C18—C17—H17107.5C28—C36—H36107.6
C19—C17—H17107.5C36—C37—H37A109.5
C9—C17—H17107.5C36—C37—H37B109.5
C17—C18—H18A109.5H37A—C37—H37B109.5
C17—C18—H18B109.5C36—C37—H37C109.5
H18A—C18—H18B109.5H37A—C37—H37C109.5
C17—C18—H18C109.5H37B—C37—H37C109.5
H18A—C18—H18C109.5C36—C38—H38A109.5
H18B—C18—H18C109.5C36—C38—H38B109.5
C17—C19—H19A109.5H38A—C38—H38B109.5
C17—C19—H19B109.5C36—C38—H38C109.5
H19A—C19—H19B109.5H38A—C38—H38C109.5
C17—C19—H19C109.5H38B—C38—H38C109.5
H19A—C19—H19C109.5C7—N1—C8121.0 (2)
H19B—C19—H19C109.5C26—N2—C27119.4 (2)
C25—C20—C21118.9 (2)C6—O1—H1109.5
C25—C20—C26119.5 (2)C21—O2—H2A109.5
C6—C1—C2—C31.5 (4)C26—C20—C21—C22179.2 (3)
C7—C1—C2—C3176.8 (3)O2—C21—C22—C23177.4 (3)
C1—C2—C3—C41.7 (5)C20—C21—C22—C232.7 (5)
C1—C2—C3—I1175.6 (2)C21—C22—C23—C241.3 (5)
C2—C3—C4—C50.1 (5)C22—C23—C24—C250.9 (5)
I1—C3—C4—C5177.2 (3)C22—C23—C24—I2176.8 (3)
C3—C4—C5—C61.7 (5)C23—C24—C25—C201.7 (4)
C4—C5—C6—O1177.4 (3)I2—C24—C25—C20176.0 (2)
C4—C5—C6—C11.8 (5)C21—C20—C25—C240.3 (4)
C2—C1—C6—O1179.0 (3)C26—C20—C25—C24177.1 (2)
C7—C1—C6—O10.7 (5)C25—C20—C26—N2176.7 (3)
C2—C1—C6—C50.2 (4)C21—C20—C26—N20.6 (4)
C7—C1—C6—C5178.5 (3)C32—C27—C28—C292.1 (4)
C2—C1—C7—N1176.9 (3)N2—C27—C28—C29179.7 (3)
C6—C1—C7—N11.3 (4)C32—C27—C28—C36178.1 (3)
C13—C8—C9—C101.1 (5)N2—C27—C28—C360.6 (4)
N1—C8—C9—C10176.6 (3)C27—C28—C29—C300.2 (5)
C13—C8—C9—C17178.6 (3)C36—C28—C29—C30179.5 (3)
N1—C8—C9—C173.0 (4)C28—C29—C30—C311.9 (6)
C8—C9—C10—C110.0 (6)C29—C30—C31—C321.4 (6)
C17—C9—C10—C11179.7 (4)C28—C27—C32—C312.6 (4)
C9—C10—C11—C120.1 (7)N2—C27—C32—C31179.8 (3)
C10—C11—C12—C130.9 (7)C28—C27—C32—C33179.3 (3)
C11—C12—C13—C82.0 (6)N2—C27—C32—C331.7 (4)
C11—C12—C13—C14179.9 (4)C30—C31—C32—C270.8 (5)
C9—C8—C13—C122.1 (5)C30—C31—C32—C33178.9 (3)
N1—C8—C13—C12177.7 (3)C27—C32—C33—C34103.9 (4)
C9—C8—C13—C14180.0 (3)C31—C32—C33—C3474.2 (5)
N1—C8—C13—C144.4 (4)C27—C32—C33—C35129.4 (5)
C12—C13—C14—C1577.3 (5)C31—C32—C33—C3552.5 (5)
C8—C13—C14—C15100.5 (4)C29—C28—C36—C3851.6 (5)
C12—C13—C14—C1646.8 (5)C27—C28—C36—C38128.2 (4)
C8—C13—C14—C16135.3 (4)C29—C28—C36—C3772.3 (5)
C10—C9—C17—C1866.9 (5)C27—C28—C36—C37107.9 (5)
C8—C9—C17—C18112.8 (4)C1—C7—N1—C8177.2 (3)
C10—C9—C17—C1957.3 (5)C13—C8—N1—C799.1 (3)
C8—C9—C17—C19123.0 (5)C9—C8—N1—C785.2 (3)
C25—C20—C21—O2178.3 (3)C20—C26—N2—C27175.8 (2)
C26—C20—C21—O20.9 (5)C32—C27—N2—C2695.2 (3)
C25—C20—C21—C221.9 (4)C28—C27—N2—C2687.2 (3)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.606 (3)147
O2—H2A···N20.821.912.617 (3)143
C16—H16A···Cg2i0.962.913.785 (5)153
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC19H22INO
Mr407.28
Crystal system, space groupTriclinic, 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)
V3)1855.00 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.73
Crystal size (mm)0.26 × 0.24 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.662, 0.724
No. of measured, independent and
observed [I > 2σ(I)] reflections
45699, 10505, 7252
Rint0.025
(sin θ/λ)max1)0.699
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.111, 1.01
No. of reflections10505
No. of parameters407
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.606 (3)147
O2—H2A···N20.821.912.617 (3)143
C16—H16A···Cg2i0.962.913.785 (5)153
Symmetry code: (i) x1, y, z.
 

Acknowledgements

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

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLin, 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
First citationRaja, 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
First citationSantos, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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