4-{(E)-[2-(4-Iodo­but­oxy)benzyl­idene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Fun, H.-K.; Hemamalini, M.; Asiri, A.M.; Khan, S.A.

doi:10.1107/S1600536810020374

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1588-o1589

doi:10.1107/S1600536810020374

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4-{(E)-[2-(4-Iodobutoxy)benzylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Abdullah M. Asiri ^b § and Salman A. Khan ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Faculty of Science, King Abdu Aziz University, Jeddah, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 26 May 2010; accepted 28 May 2010; online 5 June 2010)

The title Schiff base compound, C₂₂H₂₄IN₃O₂, adopts an E configuration about the central C=N bond. The pyrazolone ring makes a dihedral angle of 49.68 (10)° with its attached phenyl ring. The phenolate plane makes dihedral angles of 16.78 (9) and 50.54 (9)°, respectively, with the pyrazolone ring and the terminal phenyl ring. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, an intermolecular C—H⋯O hydrogen bond is also observed.

Related literature

For background to and applications of Schiff bases, see: Tarafder et al. (2002 ); Silver & Soderlund (2005 ); Vicini et al. (2003 ); Ozdemir et al. (2007 ); Joshi et al. (2004 ). For background to and the biological activity of 4-aminoantipyrene and its derivatives, see: Jain et al. (2003 ); Filho et al. (1998 ); Sondhi et al. (1999 ); Mishra (1999 ); Sondhi et al. (2001 ). For related structures, see: Eryigit & Kendi (1998 ); Manikandan et al. (2000 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₂₄IN₃O₂
M_r = 489.34
Monoclinic, P 2₁ /c
a = 11.5235 (10) Å
b = 16.4156 (14) Å
c = 11.2828 (9) Å
β = 94.010 (2)°
V = 2129.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 100 K
0.41 × 0.34 × 0.29 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.571, T_max = 0.663
36214 measured reflections
9632 independent reflections
7935 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.159
S = 1.05
9632 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 1.26 e Å⁻³
Δρ_min = −1.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1	0.93	2.30	2.995 (2)	132
C17—H17B⋯O1ⁱ	0.97	2.42	3.193 (2)	137
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020374/is2554sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020374/is2554Isup2.hkl

checkCIF report

Comment top

Schiff bases are generally synthesized from the condensation of primary amines and active carbonyl group. Various heterocyclic ring containing Schiff bases were reported to possess cytotoxic (Tarafder et al., 2002), anticonvulsant (Silver & Soderlund, 2005), antiproliferative (Vicini et al., 2003), anticancer and antifungal activities (Ozdemir et al., 2007). It's also used as ligands for the complexes synthesis (Joshi et al., 2004). As evident from the literature, it was noted that a lot of research has been carried out on Schiff bases but no work has been done on the long chain Schiff base. 4-Aminoantipyrene, which contain pyrazolone ring, is an important compound in the class analgesic agent in otic solutions in combination with other analgesic such as benzocaine and phenylephrine. Pyrazolone is a five-membered lactam ring compound containing two N atoms and ketone in the same molecule. Lactam structure is an active nucleus in pharmacological activity, especially in the class of nonsteroidal antiinflammatory agents used in the treatment of arthritis and other musculo skeletal and joint disorders. Pyrazolone derivatives, as lactam structure related compounds, are also widely used in preparing dyes and pigments. 4-Aminoantipyrene and its derivatives have potential biological activities (Jain et al., 2003). Analgesic and antiinflammatory activities of the 4-aminoantipyrene complexes were extensively studied and reported (Filho et al., 1998; Sondhi et al., 1999). Apart from that, antimicrobial and anticancer activity of the 4-aminoantipyrine derivatives and their metal complexes caught the attention of many researchers during last decade (Mishra, 1999; Sondhi et al., 2001). In this paper we report the synthesis and the crystal structure of a mono Schiff base bearing butyl iodide side chain. It is noteworthy that the alkylating agent used in this reaction is dibromo butyl, and after obtaining the O-alkylation product, the charge transfer catalyst used caused the free bromide atom to be substituted by an iodide atom.

The title compound (I) is shown in Fig. 1. The molecule adopts a trans configuration about the central C10═N3 double bond. The C—N bond lengths of N1—C6 [1.422 (2) Å], N1—C9 [1.398 (2) Å], N2—C21 [1.459 (3) Å], N2—C7 [1.365 (2) Å] and N3—C8 [1.389 (2) Å] are normal for C—N single-bond distances. The distance between C10—N3 [1.290 (2) Å] is typical for a C═ N double-bond distance. These bonds are comparable with those in N-(1H-benzoimidazol-2-ylmethyl)-N-(2,6-dichlorophenyl) amine (Eryigit & Kendi, 1998). The N1—N2 [1.403 (2) Å] single-bond length is comparable with that in 2,6-bis(3,5-dimethylpyrazol-1-ylmethyl)pyridine (Manikandan et al., 2000).

Atom O1 deviates from the pyrazoline mean plane by 0.028 (1) Å. The pyrazolone ring (C7–C9/N1/N2) is almost planar, with maximum deviation of 0.045 (2) Å for atom N2. It makes a dihedral angle of 49.68 (10)° with its attached phenyl ring (C1–C6). The phenolate residue (C11–C16/O2) is essentially planar, with maximum deviation of 0.031 (2) Å for O2. This plane makes dihedral angles of 16.78 (9) and 50.54 (9)°, respectively, with the pyrazolone ring (C7–C9/N1/N2) and the terminal (C1–C6) phenyl ring. The N2-N1-C6-C5 and C1-C6-N1-C9 torsion angles are -147.45 (18) and -116.1 (2)°, respectively.

In the crystal structure (Fig. 2), intramolecular C10—H10A···O1 hydrogen bond interactions generate an S(6) ring motif (Bernstein et al., 1995). The crystal packing is consolidated by weak non-classical intermolecular C17—H17B···O1 hydrogen bonds (Table 1). The combination of both intra and intermolecular C—H···O hydrogen bonds stabilize the crystal structure. There exists an unusual short contact between atoms I1 and C8 with a distance of 3.3606 (17) Å, which is shorter than the sum of their van der Waals radii.

Related literature top

For background to and applications of Schiff bases, see: Tarafder et al. (2002); Silver & Soderlund (2005); Vicini et al. (2003); Ozdemir et al. (2007); Joshi et al. (2004). For background to and the biological activity of 4-aminoantipyrene and its derivatives, see: Jain et al. (2003); Filho et al. (1998); Sondhi et al. (1999); Mishra (1999); Sondhi et al. (2001). For related structures, see: Eryigit & Kendi (1998); Manikandan et al. (2000). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by the reaction of mono Schiff base (1 g, 0.0032 mol) with dibromo butane (0.0016 mol) in the presence of freshly heated K₂CO₃ (0.0097 mol) and tetrabutylamonium iodide (PTC) (0.0004 mol) in dry acetone with continuous stirring at 40 °C for 8h. After the completion of the reaction, the product obtained was purified by passing through silica-gel column (60-120 mesh) and further crystallized from methanol. Yield: 65 %; m. p. 136 °C. IR (KBr) ν_max cm^-1: 3014 (C–H aromatic), 1666 (C═O), 1571 (HC═N), 1299 (C–O), 1108 (C–N). ¹H-NMR (CDCl₃) δ: 10.13 (s, 1H, C–H olefinic), 8.22-6.96 (m, 9H, C–H aromatic), 3.57 (s, O–CH₂CH₂), 3.33 (s, N–CH₃), 2.92 (s, I–CH₂), 2.22 (s,-CH₃), 2.11 (s, 2×CH₂).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) network. H atoms not involved in the hydrogen bond interactions are omitted for clarity.

4-{(E)-[2-(4-Iodobutoxy)benzylidene]amino}- 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₂H₂₄IN₃O₂	F(000) = 984
M_r = 489.34	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9944 reflections
a = 11.5235 (10) Å	θ = 2.7–35.4°
b = 16.4156 (14) Å	µ = 1.53 mm⁻¹
c = 11.2828 (9) Å	T = 100 K
β = 94.010 (2)°	Blcok, yellow
V = 2129.1 (3) Å³	0.41 × 0.34 × 0.29 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	9632 independent reflections
Radiation source: fine-focus sealed tube	7935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 35.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→18
T_min = 0.571, T_max = 0.663	k = −26→26
36214 measured reflections	l = −17→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1027P)² + 1.5532P] where P = (F_o² + 2F_c²)/3
9632 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 1.26 e Å⁻³
0 restraints	Δρ_min = −1.68 e Å⁻³

Crystal data top

C₂₂H₂₄IN₃O₂	V = 2129.1 (3) Å³
M_r = 489.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5235 (10) Å	µ = 1.53 mm⁻¹
b = 16.4156 (14) Å	T = 100 K
c = 11.2828 (9) Å	0.41 × 0.34 × 0.29 mm
β = 94.010 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	9632 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7935 reflections with I > 2σ(I)
T_min = 0.571, T_max = 0.663	R_int = 0.025
36214 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.05	Δρ_max = 1.26 e Å⁻³
9632 reflections	Δρ_min = −1.68 e Å⁻³
255 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2σ(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
I1	0.290561 (14)	0.362436 (10)	0.802978 (17)	0.03475 (7)
O1	0.68399 (13)	0.05872 (8)	0.94462 (12)	0.0192 (2)
O2	0.71122 (14)	0.22745 (9)	0.66181 (13)	0.0206 (2)
N1	0.76696 (14)	−0.05557 (10)	1.03829 (14)	0.0182 (3)
N2	0.87138 (14)	−0.09878 (10)	1.03161 (15)	0.0200 (3)
N3	0.89080 (14)	0.03071 (9)	0.78003 (13)	0.0163 (2)
C1	0.78638 (19)	−0.05051 (15)	1.25448 (18)	0.0266 (4)
H1A	0.8669	−0.0531	1.2531	0.032*
C2	0.7339 (2)	−0.04626 (17)	1.36239 (19)	0.0315 (5)
H2A	0.7798	−0.0461	1.4336	0.038*
C3	0.6135 (2)	−0.04230 (14)	1.3637 (2)	0.0275 (4)
H3A	0.5791	−0.0395	1.4357	0.033*
C4	0.54450 (18)	−0.04253 (12)	1.25739 (19)	0.0232 (3)
H4A	0.4640	−0.0392	1.2586	0.028*
C5	0.59526 (17)	−0.04769 (11)	1.14967 (18)	0.0199 (3)
H5A	0.5492	−0.0490	1.0786	0.024*
C6	0.71592 (17)	−0.05082 (11)	1.14923 (16)	0.0186 (3)
C7	0.92082 (16)	−0.07340 (11)	0.93152 (15)	0.0172 (3)
C8	0.85924 (15)	−0.00877 (10)	0.88180 (15)	0.0156 (3)
C9	0.75980 (16)	0.00540 (10)	0.95158 (15)	0.0161 (3)
C10	0.82737 (16)	0.09014 (10)	0.73798 (15)	0.0166 (3)
H10A	0.7665	0.1092	0.7803	0.020*
C11	0.85006 (16)	0.12799 (10)	0.62451 (15)	0.0160 (3)
C12	0.93106 (16)	0.09552 (11)	0.55089 (16)	0.0184 (3)
H12A	0.9768	0.0516	0.5775	0.022*
C13	0.94457 (18)	0.12744 (12)	0.43891 (17)	0.0209 (3)
H13A	0.9995	0.1057	0.3912	0.025*
C14	0.87488 (18)	0.19228 (12)	0.39885 (16)	0.0210 (3)
H14A	0.8814	0.2124	0.3226	0.025*
C15	0.79573 (17)	0.22751 (11)	0.47051 (16)	0.0195 (3)
H15A	0.7510	0.2717	0.4432	0.023*
C16	0.78371 (16)	0.19599 (10)	0.58414 (15)	0.0167 (3)
C17	0.64112 (18)	0.29607 (12)	0.62471 (18)	0.0224 (3)
H17A	0.5886	0.2813	0.5572	0.027*
H17B	0.6902	0.3403	0.6010	0.027*
C18	0.57265 (18)	0.32256 (11)	0.72692 (19)	0.0229 (3)
H18A	0.5220	0.3673	0.7010	0.027*
H18B	0.6262	0.3426	0.7905	0.027*
C19	0.49946 (19)	0.25498 (12)	0.7752 (2)	0.0244 (3)
H19A	0.4505	0.2319	0.7103	0.029*
H19B	0.5506	0.2122	0.8072	0.029*
C20	0.4233 (2)	0.28321 (15)	0.8710 (2)	0.0301 (4)
H20A	0.4709	0.3111	0.9327	0.036*
H20B	0.3884	0.2362	0.9066	0.036*
C21	0.8675 (2)	−0.18482 (14)	1.0635 (2)	0.0313 (5)
H21A	0.9438	−0.2080	1.0613	0.047*
H21B	0.8147	−0.2129	1.0080	0.047*
H21C	0.8414	−0.1902	1.1421	0.047*
C22	1.02298 (18)	−0.11555 (13)	0.88815 (18)	0.0223 (3)
H22A	1.0828	−0.1196	0.9515	0.033*
H22B	1.0517	−0.0852	0.8236	0.033*
H22C	1.0008	−0.1692	0.8612	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02522 (9)	0.03191 (10)	0.04766 (12)	0.00818 (5)	0.00638 (7)	0.01372 (6)
O1	0.0219 (6)	0.0172 (5)	0.0185 (5)	0.0063 (4)	0.0021 (4)	0.0012 (4)
O2	0.0269 (7)	0.0163 (5)	0.0188 (5)	0.0067 (5)	0.0033 (5)	0.0036 (4)
N1	0.0186 (6)	0.0191 (6)	0.0169 (6)	0.0048 (5)	0.0018 (5)	0.0040 (5)
N2	0.0181 (6)	0.0195 (6)	0.0224 (7)	0.0051 (5)	0.0023 (5)	0.0069 (5)
N3	0.0184 (6)	0.0155 (6)	0.0147 (6)	0.0014 (5)	−0.0003 (4)	0.0013 (4)
C1	0.0213 (8)	0.0392 (11)	0.0191 (8)	−0.0067 (7)	0.0002 (6)	0.0047 (7)
C2	0.0296 (10)	0.0457 (13)	0.0192 (8)	−0.0092 (9)	0.0020 (7)	0.0032 (8)
C3	0.0321 (10)	0.0283 (9)	0.0232 (8)	−0.0054 (8)	0.0091 (7)	−0.0004 (7)
C4	0.0233 (8)	0.0184 (7)	0.0288 (9)	0.0010 (6)	0.0076 (7)	0.0021 (6)
C5	0.0197 (7)	0.0165 (7)	0.0234 (8)	0.0014 (5)	0.0012 (6)	0.0012 (6)
C6	0.0200 (7)	0.0182 (7)	0.0177 (7)	−0.0004 (5)	0.0020 (5)	0.0031 (5)
C7	0.0181 (7)	0.0169 (6)	0.0162 (6)	0.0029 (5)	−0.0003 (5)	0.0028 (5)
C8	0.0174 (6)	0.0146 (6)	0.0145 (6)	0.0020 (5)	−0.0001 (5)	0.0010 (5)
C9	0.0190 (7)	0.0143 (6)	0.0149 (6)	0.0017 (5)	−0.0002 (5)	0.0008 (5)
C10	0.0206 (7)	0.0139 (6)	0.0151 (6)	0.0016 (5)	0.0005 (5)	0.0006 (5)
C11	0.0187 (7)	0.0137 (6)	0.0153 (6)	−0.0002 (5)	−0.0008 (5)	0.0002 (5)
C12	0.0204 (7)	0.0184 (7)	0.0162 (6)	0.0021 (6)	−0.0001 (5)	−0.0001 (5)
C13	0.0223 (8)	0.0235 (8)	0.0169 (7)	−0.0005 (6)	0.0027 (6)	0.0009 (6)
C14	0.0227 (8)	0.0232 (8)	0.0169 (7)	−0.0017 (6)	0.0007 (6)	0.0042 (6)
C15	0.0209 (7)	0.0187 (7)	0.0186 (7)	−0.0012 (6)	−0.0009 (6)	0.0050 (5)
C16	0.0199 (7)	0.0138 (6)	0.0162 (6)	−0.0010 (5)	−0.0001 (5)	0.0006 (5)
C17	0.0257 (8)	0.0170 (7)	0.0245 (8)	0.0053 (6)	0.0026 (6)	0.0055 (6)
C18	0.0246 (8)	0.0137 (6)	0.0304 (9)	0.0020 (6)	0.0024 (7)	0.0009 (6)
C19	0.0252 (8)	0.0172 (7)	0.0310 (9)	0.0018 (6)	0.0025 (7)	0.0036 (6)
C20	0.0298 (10)	0.0298 (10)	0.0314 (10)	0.0106 (8)	0.0063 (8)	0.0122 (8)
C21	0.0305 (10)	0.0227 (9)	0.0418 (12)	0.0084 (8)	0.0110 (9)	0.0154 (8)
C22	0.0210 (8)	0.0219 (7)	0.0243 (8)	0.0062 (6)	0.0031 (6)	0.0024 (6)

Geometric parameters (Å, º) top

I1—C20	2.111 (2)	C11—C12	1.398 (3)
O1—C9	1.235 (2)	C11—C16	1.410 (2)
O2—C16	1.355 (2)	C12—C13	1.387 (3)
O2—C17	1.432 (2)	C12—H12A	0.9300
N1—C9	1.398 (2)	C13—C14	1.390 (3)
N1—N2	1.403 (2)	C13—H13A	0.9300
N1—C6	1.422 (2)	C14—C15	1.387 (3)
N2—C7	1.365 (2)	C14—H14A	0.9300
N2—C21	1.459 (3)	C15—C16	1.398 (2)
N3—C10	1.289 (2)	C15—H15A	0.9300
N3—C8	1.389 (2)	C17—C18	1.506 (3)
C1—C6	1.391 (3)	C17—H17A	0.9700
C1—C2	1.398 (3)	C17—H17B	0.9700
C1—H1A	0.9300	C18—C19	1.518 (3)
C2—C3	1.390 (3)	C18—H18A	0.9700
C2—H2A	0.9300	C18—H18B	0.9700
C3—C4	1.392 (3)	C19—C20	1.512 (3)
C3—H3A	0.9300	C19—H19A	0.9700
C4—C5	1.388 (3)	C19—H19B	0.9700
C4—H4A	0.9300	C20—H20A	0.9700
C5—C6	1.392 (3)	C20—H20B	0.9700
C5—H5A	0.9300	C21—H21A	0.9600
C7—C8	1.374 (2)	C21—H21B	0.9600
C7—C22	1.478 (3)	C21—H21C	0.9600
C8—C9	1.454 (2)	C22—H22A	0.9600
C10—C11	1.463 (2)	C22—H22B	0.9600
C10—H10A	0.9300	C22—H22C	0.9600

C16—O2—C17	118.14 (15)	C14—C13—H13A	120.4
C9—N1—N2	109.46 (14)	C15—C14—C13	121.23 (17)
C9—N1—C6	124.67 (15)	C15—C14—H14A	119.4
N2—N1—C6	118.95 (15)	C13—C14—H14A	119.4
C7—N2—N1	107.41 (14)	C14—C15—C16	119.45 (17)
C7—N2—C21	121.40 (17)	C14—C15—H15A	120.3
N1—N2—C21	115.78 (16)	C16—C15—H15A	120.3
C10—N3—C8	118.86 (15)	O2—C16—C15	123.87 (16)
C6—C1—C2	118.8 (2)	O2—C16—C11	115.96 (15)
C6—C1—H1A	120.6	C15—C16—C11	120.17 (17)
C2—C1—H1A	120.6	O2—C17—C18	108.56 (15)
C3—C2—C1	120.3 (2)	O2—C17—H17A	110.0
C3—C2—H2A	119.9	C18—C17—H17A	110.0
C1—C2—H2A	119.9	O2—C17—H17B	110.0
C2—C3—C4	120.08 (19)	C18—C17—H17B	110.0
C2—C3—H3A	120.0	H17A—C17—H17B	108.4
C4—C3—H3A	120.0	C17—C18—C19	113.44 (16)
C5—C4—C3	120.3 (2)	C17—C18—H18A	108.9
C5—C4—H4A	119.9	C19—C18—H18A	108.9
C3—C4—H4A	119.9	C17—C18—H18B	108.9
C4—C5—C6	119.19 (18)	C19—C18—H18B	108.9
C4—C5—H5A	120.4	H18A—C18—H18B	107.7
C6—C5—H5A	120.4	C20—C19—C18	113.41 (18)
C1—C6—C5	121.36 (18)	C20—C19—H19A	108.9
C1—C6—N1	119.94 (18)	C18—C19—H19A	108.9
C5—C6—N1	118.69 (17)	C20—C19—H19B	108.9
N2—C7—C8	109.87 (15)	C18—C19—H19B	108.9
N2—C7—C22	121.27 (16)	H19A—C19—H19B	107.7
C8—C7—C22	128.82 (16)	C19—C20—I1	111.76 (15)
C7—C8—N3	122.69 (16)	C19—C20—H20A	109.3
C7—C8—C9	107.86 (15)	I1—C20—H20A	109.3
N3—C8—C9	129.42 (15)	C19—C20—H20B	109.3
O1—C9—N1	123.96 (16)	I1—C20—H20B	109.3
O1—C9—C8	131.28 (16)	H20A—C20—H20B	107.9
N1—C9—C8	104.73 (14)	N2—C21—H21A	109.5
N3—C10—C11	120.79 (16)	N2—C21—H21B	109.5
N3—C10—H10A	119.6	H21A—C21—H21B	109.5
C11—C10—H10A	119.6	N2—C21—H21C	109.5
C12—C11—C16	118.64 (16)	H21A—C21—H21C	109.5
C12—C11—C10	121.71 (16)	H21B—C21—H21C	109.5
C16—C11—C10	119.52 (16)	C7—C22—H22A	109.5
C13—C12—C11	121.30 (17)	C7—C22—H22B	109.5
C13—C12—H12A	119.3	H22A—C22—H22B	109.5
C11—C12—H12A	119.3	C7—C22—H22C	109.5
C12—C13—C14	119.12 (18)	H22A—C22—H22C	109.5
C12—C13—H13A	120.4	H22B—C22—H22C	109.5

C9—N1—N2—C7	−8.6 (2)	C6—N1—C9—O1	−21.4 (3)
C6—N1—N2—C7	−160.89 (17)	N2—N1—C9—C8	6.5 (2)
C9—N1—N2—C21	−147.91 (19)	C6—N1—C9—C8	156.82 (17)
C6—N1—N2—C21	59.8 (2)	C7—C8—C9—O1	175.93 (19)
C6—C1—C2—C3	−0.1 (4)	N3—C8—C9—O1	−6.2 (3)
C1—C2—C3—C4	0.0 (4)	C7—C8—C9—N1	−2.11 (19)
C2—C3—C4—C5	0.8 (3)	N3—C8—C9—N1	175.74 (17)
C3—C4—C5—C6	−1.4 (3)	C8—N3—C10—C11	−173.62 (16)
C2—C1—C6—C5	−0.5 (3)	N3—C10—C11—C12	7.8 (3)
C2—C1—C6—N1	−179.6 (2)	N3—C10—C11—C16	−176.25 (17)
C4—C5—C6—C1	1.3 (3)	C16—C11—C12—C13	−1.8 (3)
C4—C5—C6—N1	−179.60 (17)	C10—C11—C12—C13	174.17 (18)
C9—N1—C6—C1	−116.1 (2)	C11—C12—C13—C14	−0.9 (3)
N2—N1—C6—C1	31.7 (3)	C12—C13—C14—C15	2.6 (3)
C9—N1—C6—C5	64.8 (3)	C13—C14—C15—C16	−1.6 (3)
N2—N1—C6—C5	−147.45 (18)	C17—O2—C16—C15	1.2 (3)
N1—N2—C7—C8	7.2 (2)	C17—O2—C16—C11	−179.42 (17)
C21—N2—C7—C8	143.72 (19)	C14—C15—C16—O2	178.16 (18)
N1—N2—C7—C22	−170.71 (17)	C14—C15—C16—C11	−1.2 (3)
C21—N2—C7—C22	−34.2 (3)	C12—C11—C16—O2	−176.58 (16)
N2—C7—C8—N3	178.79 (16)	C10—C11—C16—O2	7.4 (2)
C22—C7—C8—N3	−3.5 (3)	C12—C11—C16—C15	2.8 (3)
N2—C7—C8—C9	−3.2 (2)	C10—C11—C16—C15	−173.23 (17)
C22—C7—C8—C9	174.55 (19)	C16—O2—C17—C18	−177.32 (16)
C10—N3—C8—C7	178.99 (17)	O2—C17—C18—C19	−55.7 (2)
C10—N3—C8—C9	1.4 (3)	C17—C18—C19—C20	−175.30 (18)
N2—N1—C9—O1	−171.71 (17)	C18—C19—C20—I1	67.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1	0.93	2.30	2.995 (2)	132
C17—H17B···O1ⁱ	0.97	2.42	3.193 (2)	137

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄IN₃O₂
M_r	489.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.5235 (10), 16.4156 (14), 11.2828 (9)
β (°)	94.010 (2)
V (Å³)	2129.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.41 × 0.34 × 0.29

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.571, 0.663
No. of measured, independent and observed [I > 2σ(I)] reflections	36214, 9632, 7935
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.819

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.159, 1.05
No. of reflections	9632
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.26, −1.68

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1	0.93	2.30	2.995 (2)	132
C17—H17B···O1ⁱ	0.97	2.42	3.193 (2)	137

Symmetry code: (i) x, −y+1/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§On secondment to: The Center of Excellence for Advanced Materials Research, King Abdu Aziz University, Jeddah 21589, Saudi Arabia.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. AMA and SAK thank the Chemistry Department, King Abdul Aziz University, Jeddah, for providing research facilities.

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