2-Iodo-N-(6-methyl-2-pyrid­yl)benzamide

Fun, H.-K.; Kia, R.; Maity, A.C.; Maity, S.; Goswami, S.

doi:10.1107/S1600536808041950

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o118-o119

doi:10.1107/S1600536808041950

Open

access

2-Iodo-N-(6-methyl-2-pyridyl)benzamide

Hoong-Kun Fun,^a ^* Reza Kia,^a Annada C. Maity,^b Sibaprasad Maity ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 6 December 2008; accepted 10 December 2008; online 13 December 2008)

The asymmetric unit of the title compound, C₁₃H₁₁IN₂O, comprises two crystallographically independent molecules. The dihedral angles between the ring planes are 53.56 (9) and 72.14 (19)° in the two molecules. Pairs of intermolecular N—H⋯N hydrogen bonds and I⋯O interactions link neighbouring molecules into two different pairs of dimers, those involving N—H⋯N interactions having R²₂(8) ring motifs. Short intermolecular I⋯O [3.1458 (15) Å] and I⋯N [3.4834 (16) Å] contacts are present. The crystal structure is further stabilized by intermolecular C—H⋯π interactions [3.565 (2) and 3.629 (2) Å].

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For applications in supramolecular chemistry and molecular recognition, see, for example: Goswami & Dey (2006 ); Goswami et al. (2005a ,b ); Steed & Atwood (2001 ); Lehn (1995 ); Desiraju (2003 ).

Experimental

Crystal data

C₁₃H₁₁IN₂O
M_r = 338.14
Triclinic, $[P \overline 1]$
a = 9.8687 (3) Å
b = 10.1276 (3) Å
c = 13.6366 (4) Å
α = 97.521 (1)°
β = 93.113 (1)°
γ = 110.380 (1)°
V = 1259.28 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.53 mm⁻¹
T = 100.0 (1) K
0.49 × 0.32 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.374, T_max = 0.746
47136 measured reflections
11804 independent reflections
9568 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 1.05
11804 reflections
317 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.34 e Å⁻³
Δρ_min = −1.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯N2Bⁱ	0.83 (3)	2.14 (3)	2.962 (2)	172 (3)
N1B—H1NB⋯N2Aⁱ	0.84 (3)	2.25 (3)	3.079 (2)	169 (2)
C9A—H9AA⋯O1A	0.93	2.40	2.895 (2)	113
C5B—H5BA⋯O1Aⁱⁱ	0.93	2.58	3.359 (2)	141
C9B—H9BA⋯O1B	0.93	2.26	2.825 (3)	118
C11A—H11A⋯O1Bⁱⁱⁱ	0.93	2.48	3.254 (2)	141
C4B—H4BA⋯Cg1ⁱⁱ	0.93	2.71	3.565 (2)	153
C13A—H13C⋯Cg2ⁱ	0.96	2.85	3.629 (2)	139
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+1, -y, -z+1. Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041950/tk2344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041950/tk2344Isup2.hkl

checkCIF report

Comment top

The role of hydrogen bonds involving neutral amidic-type NH and carbonyl type O-atom in the controlled assembly of biologically relevant molecules giving outstanding architectures is an obvious entity in nature. Amide derivatives of heterocyclic compounds are important hydrogen bonding synthons as they are the very useful substrates which can be used for the synthesis of designed receptors in the field of molecular recognition (Goswami & Dey 2006 a; Goswami et al., 2005a) and supramolecular chemistry (Steed & Atwood 2001; Lehn 1995; Desiraju 2003). We have previously reported the design and synthesis of a series of symmetric diamido biaryls by direct homocoupling of iodoarylbenzamides (Goswmai et al. 2005b).

In the title compound (I), Fig. 1, intramolecular C—H···O hydrogen bonds generate six-membered rings, producing S(6) ring motifs. Pairs of intermolecular N—H···N hydrogen bonds and I···O interactions link neighbouring molecules into two different pairs of dimers, those involving N—H···N interactions having R²₂(8) ring motifs (Fig. 2). The interesting features of the crystal structure are the short intermolecular I···O [3.1458 (15) Å; symmetry: 1 - x, 1 - y, -z] and I···N [3.4834 (16) Å; symmetry: x, y, z] contacts which are significanlty shorter than the sum of the van der Waals radii of these atoms. The crystal structure is further stabilized by intermolecular C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B benzene rings).

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For applications in supramolecular chemistry and molecular recognition, see, for example: Goswami & Dey (2006); Goswami et al. (2005a,b); Steed & Atwood (2001); Lehn (1995); Desiraju (2003). Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

Experimental top

To a magnetically stirred solution of the 2-amino-6-methylpyridine (108 mg, 1.0 mmol) in dry CH₂Cl₂ (20 ml) and freshly distilled triethylamine (1.2 equiv), was added 2-iodobenzoyl chloride (1.1 equiv). Stirring was continued for 12 h. The triethylamine hydrochloride was filtered off, the organic layer after washing with water was dried (anhydrous Na₂SO₄) and then the solvent was removed under reduced pressure. The residue was purified using column chromatography on silica-gel to afford (I) (310 mg, 92%).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Dashed lines show intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the b-axis, showing pairs of dimers with R²₂(8) motifs linked together through N—H···N interactions and other pairs of dimers linked together by I···O interactions. Intermolecular interactions are drawn as dashed lines.

2-Iodo-N-(6-methyl-2-pyridyl)benzamide top

Crystal data top

C₁₃H₁₁IN₂O	Z = 4
M_r = 338.14	F(000) = 656
Triclinic, P1	D_x = 1.784 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8687 (3) Å	Cell parameters from 9385 reflections
b = 10.1276 (3) Å	θ = 2.5–35.9°
c = 13.6366 (4) Å	µ = 2.53 mm⁻¹
α = 97.521 (1)°	T = 100 K
β = 93.113 (1)°	Plate, colourless
γ = 110.380 (1)°	0.49 × 0.32 × 0.12 mm
V = 1259.28 (6) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	11804 independent reflections
Radiation source: fine-focus sealed tube	9568 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 36.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
T_min = 0.374, T_max = 0.746	k = −16→16
47136 measured reflections	l = −22→21

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0498P)²] where P = (F_o² + 2F_c²)/3
11804 reflections	(Δ/σ)_max = 0.002
317 parameters	Δρ_max = 2.34 e Å⁻³
0 restraints	Δρ_min = −1.51 e Å⁻³

Crystal data top

C₁₃H₁₁IN₂O	γ = 110.380 (1)°
M_r = 338.14	V = 1259.28 (6) Å³
Triclinic, P1	Z = 4
a = 9.8687 (3) Å	Mo Kα radiation
b = 10.1276 (3) Å	µ = 2.53 mm⁻¹
c = 13.6366 (4) Å	T = 100 K
α = 97.521 (1)°	0.49 × 0.32 × 0.12 mm
β = 93.113 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	11804 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	9568 reflections with I > 2σ(I)
T_min = 0.374, T_max = 0.746	R_int = 0.036
47136 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 2.34 e Å⁻³
11804 reflections	Δρ_min = −1.51 e Å⁻³
317 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
I1A	0.600768 (13)	0.719329 (12)	0.055937 (8)	0.02055 (4)
O1A	0.73426 (15)	0.40166 (14)	0.01538 (10)	0.0225 (3)
N1A	0.71156 (17)	0.46318 (15)	0.17981 (11)	0.0178 (3)
N2A	0.53614 (17)	0.34154 (15)	0.27329 (11)	0.0179 (3)
C1A	0.8221 (2)	0.75540 (18)	0.08834 (12)	0.0181 (3)
C2A	0.9243 (2)	0.89336 (19)	0.09553 (14)	0.0229 (3)
H2AA	0.8937	0.9700	0.0928	0.027*
C3A	1.0713 (2)	0.9156 (2)	0.10670 (14)	0.0246 (4)
H3AA	1.1393	1.0077	0.1128	0.030*
C4A	1.1178 (2)	0.8017 (2)	0.10882 (14)	0.0245 (4)
H4AA	1.2166	0.8169	0.1141	0.029*
C5A	1.0165 (2)	0.6648 (2)	0.10306 (14)	0.0228 (3)
H5AA	1.0479	0.5885	0.1049	0.027*
C6A	0.86799 (19)	0.64057 (17)	0.09455 (12)	0.0176 (3)
C7A	0.76383 (19)	0.49040 (17)	0.09119 (13)	0.0174 (3)
C8A	0.61757 (19)	0.32996 (17)	0.19928 (12)	0.0170 (3)
C9A	0.6157 (2)	0.20087 (18)	0.14923 (14)	0.0218 (3)
H9AA	0.6738	0.1973	0.0983	0.026*
C10A	0.5238 (2)	0.07761 (19)	0.17815 (16)	0.0260 (4)
H10A	0.5191	−0.0112	0.1464	0.031*
C11A	0.4392 (2)	0.08663 (19)	0.25418 (15)	0.0243 (4)
H11A	0.3774	0.0043	0.2741	0.029*
C12A	0.4472 (2)	0.22025 (19)	0.30064 (14)	0.0206 (3)
C13A	0.3562 (2)	0.2346 (2)	0.38233 (16)	0.0267 (4)
H13A	0.4006	0.3270	0.4226	0.040*
H13B	0.3485	0.1620	0.4227	0.040*
H13C	0.2610	0.2241	0.3543	0.040*
I1B	0.755985 (14)	0.434720 (13)	0.498669 (9)	0.02504 (4)
O1B	0.64755 (17)	0.24584 (15)	0.71745 (14)	0.0330 (4)
N1B	0.49390 (17)	0.36405 (15)	0.68719 (11)	0.0176 (3)
N2B	0.24463 (17)	0.28564 (15)	0.66686 (11)	0.0182 (3)
C1B	0.8325 (2)	0.53935 (18)	0.64543 (13)	0.0194 (3)
C2B	0.9594 (2)	0.65908 (19)	0.66103 (14)	0.0221 (3)
H2BA	1.0122	0.6876	0.6082	0.027*
C3B	1.0066 (2)	0.7357 (2)	0.75644 (14)	0.0229 (3)
H3BA	1.0923	0.8151	0.7677	0.027*
C4B	0.9267 (2)	0.6946 (2)	0.83480 (14)	0.0244 (4)
H4BA	0.9578	0.7474	0.8983	0.029*
C5B	0.7997 (2)	0.57396 (19)	0.81873 (14)	0.0217 (3)
H5BA	0.7461	0.5464	0.8714	0.026*
C6B	0.75314 (19)	0.49482 (17)	0.72370 (12)	0.0170 (3)
C7B	0.6259 (2)	0.35554 (18)	0.70882 (13)	0.0199 (3)
C8B	0.3617 (2)	0.24816 (17)	0.66336 (12)	0.0180 (3)
C9B	0.3545 (2)	0.10825 (18)	0.63597 (14)	0.0222 (3)
H9BA	0.4381	0.0859	0.6336	0.027*
C10B	0.2170 (2)	0.0036 (2)	0.61241 (15)	0.0265 (4)
H10B	0.2071	−0.0914	0.5948	0.032*
C11B	0.0950 (2)	0.0406 (2)	0.61509 (14)	0.0257 (4)
H11B	0.0027	−0.0291	0.5998	0.031*
C12B	0.1116 (2)	0.18363 (19)	0.64094 (13)	0.0214 (3)
C13B	−0.0153 (2)	0.2316 (2)	0.63969 (16)	0.0282 (4)
H13D	0.0075	0.3177	0.6866	0.042*
H13E	−0.0983	0.1587	0.6574	0.042*
H13F	−0.0367	0.2494	0.5742	0.042*
H1NA	0.728 (3)	0.530 (3)	0.2269 (19)	0.030 (7)*
H1NB	0.485 (3)	0.444 (3)	0.6892 (19)	0.035 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1A	0.02262 (6)	0.01832 (5)	0.02205 (6)	0.00989 (4)	0.00152 (4)	0.00112 (4)
O1A	0.0268 (7)	0.0187 (6)	0.0190 (6)	0.0057 (5)	0.0032 (5)	−0.0012 (5)
N1A	0.0217 (7)	0.0118 (5)	0.0179 (6)	0.0038 (5)	0.0027 (5)	0.0008 (5)
N2A	0.0194 (7)	0.0138 (6)	0.0189 (6)	0.0039 (5)	0.0009 (5)	0.0029 (5)
C1A	0.0212 (8)	0.0158 (7)	0.0170 (7)	0.0062 (6)	0.0022 (6)	0.0022 (5)
C2A	0.0295 (10)	0.0152 (7)	0.0217 (8)	0.0057 (7)	0.0019 (7)	0.0021 (6)
C3A	0.0274 (10)	0.0179 (7)	0.0231 (8)	0.0018 (7)	−0.0004 (7)	0.0034 (6)
C4A	0.0205 (9)	0.0229 (8)	0.0267 (9)	0.0033 (7)	0.0022 (7)	0.0047 (7)
C5A	0.0220 (9)	0.0209 (8)	0.0259 (8)	0.0076 (7)	0.0028 (7)	0.0051 (7)
C6A	0.0202 (8)	0.0150 (6)	0.0167 (7)	0.0055 (6)	0.0019 (6)	0.0018 (5)
C7A	0.0187 (8)	0.0151 (6)	0.0189 (7)	0.0067 (6)	0.0026 (6)	0.0027 (5)
C8A	0.0198 (8)	0.0126 (6)	0.0180 (7)	0.0055 (6)	−0.0002 (6)	0.0023 (5)
C9A	0.0269 (9)	0.0141 (7)	0.0255 (8)	0.0093 (6)	0.0020 (7)	0.0013 (6)
C10A	0.0304 (10)	0.0119 (7)	0.0344 (10)	0.0075 (7)	0.0004 (8)	0.0004 (7)
C11A	0.0249 (9)	0.0140 (7)	0.0322 (10)	0.0045 (6)	−0.0003 (7)	0.0054 (7)
C12A	0.0189 (8)	0.0165 (7)	0.0260 (8)	0.0051 (6)	0.0007 (6)	0.0065 (6)
C13A	0.0278 (10)	0.0204 (8)	0.0317 (10)	0.0062 (7)	0.0077 (8)	0.0085 (7)
I1B	0.02984 (7)	0.02357 (6)	0.01716 (6)	0.00598 (5)	0.00087 (4)	−0.00172 (4)
O1B	0.0255 (7)	0.0141 (6)	0.0585 (10)	0.0062 (5)	−0.0030 (7)	0.0086 (6)
N1B	0.0201 (7)	0.0113 (5)	0.0198 (6)	0.0037 (5)	0.0015 (5)	0.0023 (5)
N2B	0.0196 (7)	0.0167 (6)	0.0161 (6)	0.0040 (5)	0.0008 (5)	0.0026 (5)
C1B	0.0211 (8)	0.0171 (7)	0.0183 (7)	0.0057 (6)	0.0016 (6)	0.0010 (6)
C2B	0.0214 (8)	0.0192 (7)	0.0219 (8)	0.0029 (6)	0.0045 (6)	0.0016 (6)
C3B	0.0209 (9)	0.0184 (7)	0.0237 (8)	0.0017 (6)	0.0000 (6)	0.0000 (6)
C4B	0.0308 (10)	0.0172 (7)	0.0187 (8)	0.0024 (7)	−0.0008 (7)	−0.0004 (6)
C5B	0.0279 (9)	0.0169 (7)	0.0184 (7)	0.0054 (7)	0.0037 (6)	0.0032 (6)
C6B	0.0177 (8)	0.0129 (6)	0.0192 (7)	0.0040 (6)	0.0009 (6)	0.0026 (5)
C7B	0.0221 (8)	0.0142 (7)	0.0226 (8)	0.0053 (6)	0.0030 (6)	0.0034 (6)
C8B	0.0231 (8)	0.0128 (6)	0.0155 (7)	0.0031 (6)	0.0006 (6)	0.0028 (5)
C9B	0.0246 (9)	0.0132 (7)	0.0253 (8)	0.0037 (6)	−0.0006 (7)	0.0005 (6)
C10B	0.0320 (11)	0.0139 (7)	0.0265 (9)	0.0014 (7)	−0.0041 (8)	0.0014 (6)
C11B	0.0241 (9)	0.0190 (8)	0.0252 (9)	−0.0023 (7)	−0.0029 (7)	0.0036 (7)
C12B	0.0219 (9)	0.0206 (8)	0.0174 (7)	0.0023 (6)	−0.0002 (6)	0.0038 (6)
C13B	0.0203 (9)	0.0316 (10)	0.0284 (9)	0.0053 (8)	−0.0006 (7)	0.0023 (8)

Geometric parameters (Å, º) top

I1A—C1A	2.0966 (18)	I1B—C1B	2.1027 (17)
O1A—C7A	1.226 (2)	O1B—C7B	1.221 (2)
N1A—C7A	1.363 (2)	N1B—C7B	1.354 (2)
N1A—C8A	1.414 (2)	N1B—C8B	1.404 (2)
N1A—H1NA	0.83 (3)	N1B—H1NB	0.84 (3)
N2A—C8A	1.342 (2)	N2B—C8B	1.337 (2)
N2A—C12A	1.350 (2)	N2B—C12B	1.351 (2)
C1A—C2A	1.397 (2)	C1B—C6B	1.388 (2)
C1A—C6A	1.398 (2)	C1B—C2B	1.389 (3)
C2A—C3A	1.386 (3)	C2B—C3B	1.389 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.385 (3)	C3B—C4B	1.384 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.388 (3)	C4B—C5B	1.395 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.394 (3)	C5B—C6B	1.393 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.503 (2)	C6B—C7B	1.507 (2)
C8A—C9A	1.387 (2)	C8B—C9B	1.393 (2)
C9A—C10A	1.384 (3)	C9B—C10B	1.389 (3)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.379 (3)	C10B—C11B	1.381 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.391 (3)	C11B—C12B	1.394 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.492 (3)	C12B—C13B	1.493 (3)
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600

C7A—N1A—C8A	125.92 (15)	C7B—N1B—C8B	125.89 (15)
C7A—N1A—H1NA	120.2 (18)	C7B—N1B—H1NB	120.7 (19)
C8A—N1A—H1NA	113.6 (18)	C8B—N1B—H1NB	113.4 (19)
C8A—N2A—C12A	117.99 (15)	C8B—N2B—C12B	118.81 (16)
C2A—C1A—C6A	120.10 (17)	C6B—C1B—C2B	121.01 (16)
C2A—C1A—I1A	119.55 (13)	C6B—C1B—I1B	120.61 (13)
C6A—C1A—I1A	120.14 (13)	C2B—C1B—I1B	118.26 (13)
C3A—C2A—C1A	119.77 (17)	C3B—C2B—C1B	119.29 (17)
C3A—C2A—H2AA	120.1	C3B—C2B—H2BA	120.4
C1A—C2A—H2AA	120.1	C1B—C2B—H2BA	120.4
C4A—C3A—C2A	120.51 (18)	C4B—C3B—C2B	120.32 (17)
C4A—C3A—H3AA	119.7	C4B—C3B—H3BA	119.8
C2A—C3A—H3AA	119.7	C2B—C3B—H3BA	119.8
C3A—C4A—C5A	119.77 (18)	C3B—C4B—C5B	120.11 (17)
C3A—C4A—H4AA	120.1	C3B—C4B—H4BA	119.9
C5A—C4A—H4AA	120.1	C5B—C4B—H4BA	119.9
C4A—C5A—C6A	120.64 (17)	C6B—C5B—C4B	119.94 (17)
C4A—C5A—H5AA	119.7	C6B—C5B—H5BA	120.0
C6A—C5A—H5AA	119.7	C4B—C5B—H5BA	120.0
C5A—C6A—C1A	119.12 (16)	C1B—C6B—C5B	119.29 (16)
C5A—C6A—C7A	118.07 (15)	C1B—C6B—C7B	120.77 (15)
C1A—C6A—C7A	122.80 (16)	C5B—C6B—C7B	119.71 (15)
O1A—C7A—N1A	124.45 (16)	O1B—C7B—N1B	125.15 (17)
O1A—C7A—C6A	121.70 (16)	O1B—C7B—C6B	119.13 (17)
N1A—C7A—C6A	113.81 (14)	N1B—C7B—C6B	115.71 (14)
N2A—C8A—C9A	123.90 (16)	N2B—C8B—C9B	123.56 (16)
N2A—C8A—N1A	113.34 (14)	N2B—C8B—N1B	113.63 (14)
C9A—C8A—N1A	122.70 (17)	C9B—C8B—N1B	122.78 (17)
C10A—C9A—C8A	117.33 (18)	C10B—C9B—C8B	117.12 (18)
C10A—C9A—H9AA	121.3	C10B—C9B—H9BA	121.4
C8A—C9A—H9AA	121.3	C8B—C9B—H9BA	121.4
C11A—C10A—C9A	119.90 (17)	C11B—C10B—C9B	120.02 (18)
C11A—C10A—H10A	120.1	C11B—C10B—H10B	120.0
C9A—C10A—H10A	120.1	C9B—C10B—H10B	120.0
C10A—C11A—C12A	119.28 (18)	C10B—C11B—C12B	119.32 (17)
C10A—C11A—H11A	120.4	C10B—C11B—H11B	120.3
C12A—C11A—H11A	120.4	C12B—C11B—H11B	120.3
N2A—C12A—C11A	121.60 (18)	N2B—C12B—C11B	121.10 (18)
N2A—C12A—C13A	117.44 (16)	N2B—C12B—C13B	116.96 (17)
C11A—C12A—C13A	120.95 (17)	C11B—C12B—C13B	121.93 (17)
C12A—C13A—H13A	109.5	C12B—C13B—H13D	109.5
C12A—C13A—H13B	109.5	C12B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C12A—C13A—H13C	109.5	C12B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5

C6A—C1A—C2A—C3A	1.4 (3)	C6B—C1B—C2B—C3B	−0.5 (3)
I1A—C1A—C2A—C3A	−173.36 (14)	I1B—C1B—C2B—C3B	175.59 (14)
C1A—C2A—C3A—C4A	1.3 (3)	C1B—C2B—C3B—C4B	−1.1 (3)
C2A—C3A—C4A—C5A	−2.2 (3)	C2B—C3B—C4B—C5B	1.3 (3)
C3A—C4A—C5A—C6A	0.4 (3)	C3B—C4B—C5B—C6B	0.0 (3)
C4A—C5A—C6A—C1A	2.2 (3)	C2B—C1B—C6B—C5B	1.8 (3)
C4A—C5A—C6A—C7A	−178.51 (17)	I1B—C1B—C6B—C5B	−174.20 (13)
C2A—C1A—C6A—C5A	−3.1 (3)	C2B—C1B—C6B—C7B	−172.64 (17)
I1A—C1A—C6A—C5A	171.60 (13)	I1B—C1B—C6B—C7B	11.3 (2)
C2A—C1A—C6A—C7A	177.67 (16)	C4B—C5B—C6B—C1B	−1.5 (3)
I1A—C1A—C6A—C7A	−7.6 (2)	C4B—C5B—C6B—C7B	172.96 (17)
C8A—N1A—C7A—O1A	0.8 (3)	C8B—N1B—C7B—O1B	−5.4 (3)
C8A—N1A—C7A—C6A	−176.93 (15)	C8B—N1B—C7B—C6B	175.15 (16)
C5A—C6A—C7A—O1A	−77.9 (2)	C1B—C6B—C7B—O1B	86.5 (2)
C1A—C6A—C7A—O1A	101.3 (2)	C5B—C6B—C7B—O1B	−87.9 (2)
C5A—C6A—C7A—N1A	99.94 (19)	C1B—C6B—C7B—N1B	−94.0 (2)
C1A—C6A—C7A—N1A	−80.8 (2)	C5B—C6B—C7B—N1B	91.6 (2)
C12A—N2A—C8A—C9A	0.1 (3)	C12B—N2B—C8B—C9B	−1.2 (3)
C12A—N2A—C8A—N1A	−177.17 (15)	C12B—N2B—C8B—N1B	177.04 (14)
C7A—N1A—C8A—N2A	−153.70 (16)	C7B—N1B—C8B—N2B	165.94 (16)
C7A—N1A—C8A—C9A	29.0 (3)	C7B—N1B—C8B—C9B	−15.8 (3)
N2A—C8A—C9A—C10A	0.0 (3)	N2B—C8B—C9B—C10B	−0.7 (3)
N1A—C8A—C9A—C10A	177.00 (17)	N1B—C8B—C9B—C10B	−178.83 (17)
C8A—C9A—C10A—C11A	−0.2 (3)	C8B—C9B—C10B—C11B	1.1 (3)
C9A—C10A—C11A—C12A	0.2 (3)	C9B—C10B—C11B—C12B	0.4 (3)
C8A—N2A—C12A—C11A	0.0 (3)	C8B—N2B—C12B—C11B	2.8 (3)
C8A—N2A—C12A—C13A	−179.40 (16)	C8B—N2B—C12B—C13B	−176.19 (16)
C10A—C11A—C12A—N2A	−0.1 (3)	C10B—C11B—C12B—N2B	−2.4 (3)
C10A—C11A—C12A—C13A	179.25 (17)	C10B—C11B—C12B—C13B	176.50 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···N2Bⁱ	0.83 (3)	2.14 (3)	2.962 (2)	172 (3)
N1B—H1NB···N2Aⁱ	0.84 (3)	2.25 (3)	3.079 (2)	169 (2)
C9A—H9AA···O1A	0.93	2.40	2.895 (2)	113
C5B—H5BA···O1Aⁱⁱ	0.93	2.58	3.359 (2)	141
C9B—H9BA···O1B	0.93	2.26	2.825 (3)	118
C11A—H11A···O1Bⁱⁱⁱ	0.93	2.48	3.254 (2)	141
C4B—H4BA···Cg1ⁱⁱ	0.93	2.71	3.565 (2)	153
C13A—H13C···Cg2ⁱ	0.96	2.85	3.629 (2)	139

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁IN₂O
M_r	338.14
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.8687 (3), 10.1276 (3), 13.6366 (4)
α, β, γ (°)	97.521 (1), 93.113 (1), 110.380 (1)
V (Å³)	1259.28 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.53
Crystal size (mm)	0.49 × 0.32 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.374, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	47136, 11804, 9568
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.827

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 1.05
No. of reflections	11804
No. of parameters	317
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.34, −1.51

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···N2Bⁱ	0.83 (3)	2.14 (3)	2.962 (2)	172 (3)
N1B—H1NB···N2Aⁱ	0.84 (3)	2.25 (3)	3.079 (2)	169 (2)
C9A—H9AA···O1A	0.9300	2.4000	2.895 (2)	113.00
C5B—H5BA···O1Aⁱⁱ	0.9300	2.5800	3.359 (2)	141.00
C9B—H9BA···O1B	0.9300	2.2600	2.825 (3)	118.00
C11A—H11A···O1Bⁱⁱⁱ	0.9300	2.4800	3.254 (2)	141.00
C4B—H4BA···Cg1ⁱⁱ	0.9300	2.7100	3.565 (2)	153
C13A—H13C···Cg2ⁱ	0.9600	2.8500	3.629 (2)	139

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y, −z+1.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. We thank the DST [SR/S1/OC-13/2005], Government of India, for financial support. ACM thanks the UGC, Government of India, for a fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. (2003). Editor. Crystal Design: Structure and Function. In Perspectives in Supramolecular Chemistry, Vol. 7, p. 408. Chichester: John Wiley & Sons Ltd. Google Scholar
Goswami, S. P., Adak, A., Mukherjee, R., Jana, S., Dey, S. & Gallagher, J. F. (2005b). Tetrahedron, 61, 4289–4295. Web of Science CSD CrossRef CAS Google Scholar
Goswami, S. P. & Dey, S. J. (2006). J. Org. Chem. 71, 7280–7287. Web of Science CrossRef PubMed CAS Google Scholar
Goswami, S. P., Mukherjee, R. & Roy, J. (2005a). Org. Lett. 7, 1283–1285. Web of Science CrossRef PubMed CAS Google Scholar
Lehn, J.-M. (1995). Supramolecular Chemistry: Concepts and Perspectives. Weinheim: VCH. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steed, J. W. & Atwood, J. L. (2001). Supramolecular Chemistry. New York: John Wiley & Sons. Google Scholar