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Acta Cryst. (2009). E65, o118-o119    [ doi:10.1107/S1600536808041950 ]

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

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

Abstract top

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...[pi] interactions [3.565 (2) and 3.629 (2) Å].

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%).

Refinement top

N-bound hydrogen atoms were located from a difference Fourier map and refined freely; see Table 1 for N—H distances. The remaining H atoms were positioned geometrically with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl), and refined in the riding model approximation with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was used for the methyl groups. The highest peak (2.34 e. Å-3) is located 0.70 Å from I1A and the deepest hole (-1.51 e. Å-3) is located 0.75 Å from I1A.

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
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Dashed lines show intramolecular hydrogen bonds.
[Figure 2] 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
C13H11IN2OZ = 4
Mr = 338.14F(000) = 656
Triclinic, P1Dx = 1.784 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8687 (3) ÅCell parameters from 9385 reflections
b = 10.1276 (3) Åθ = 2.5–35.9°
c = 13.6366 (4) ŵ = 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 tube9568 reflections with I > 2σ(I)
graphiteRint = 0.036
φ and ω scansθmax = 36.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −16→16
Tmin = 0.374, Tmax = 0.746k = −16→16
47136 measured reflectionsl = −22→21
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0498P)2]
where P = (Fo2 + 2Fc2)/3
11804 reflections(Δ/σ)max = 0.002
317 parametersΔρmax = 2.34 e Å−3
0 restraintsΔρmin = −1.51 e Å−3
Crystal data top
C13H11IN2Oγ = 110.380 (1)°
Mr = 338.14V = 1259.28 (6) Å3
Triclinic, P1Z = 4
a = 9.8687 (3) ÅMo Kα radiation
b = 10.1276 (3) ŵ = 2.53 mm−1
c = 13.6366 (4) ÅT = 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)
Tmin = 0.374, Tmax = 0.746Rint = 0.036
47136 measured reflectionsθmax = 36.0°
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090Δρmax = 2.34 e Å−3
S = 1.05Δρmin = −1.51 e Å−3
11804 reflectionsAbsolute structure: ?
317 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
I1A0.600768 (13)0.719329 (12)0.055937 (8)0.02055 (4)
O1A0.73426 (15)0.40166 (14)0.01538 (10)0.0225 (3)
N1A0.71156 (17)0.46318 (15)0.17981 (11)0.0178 (3)
N2A0.53614 (17)0.34154 (15)0.27329 (11)0.0179 (3)
C1A0.8221 (2)0.75540 (18)0.08834 (12)0.0181 (3)
C2A0.9243 (2)0.89336 (19)0.09553 (14)0.0229 (3)
H2AA0.89370.97000.09280.027*
C3A1.0713 (2)0.9156 (2)0.10670 (14)0.0246 (4)
H3AA1.13931.00770.11280.030*
C4A1.1178 (2)0.8017 (2)0.10882 (14)0.0245 (4)
H4AA1.21660.81690.11410.029*
C5A1.0165 (2)0.6648 (2)0.10306 (14)0.0228 (3)
H5AA1.04790.58850.10490.027*
C6A0.86799 (19)0.64057 (17)0.09455 (12)0.0176 (3)
C7A0.76383 (19)0.49040 (17)0.09119 (13)0.0174 (3)
C8A0.61757 (19)0.32996 (17)0.19928 (12)0.0170 (3)
C9A0.6157 (2)0.20087 (18)0.14923 (14)0.0218 (3)
H9AA0.67380.19730.09830.026*
C10A0.5238 (2)0.07761 (19)0.17815 (16)0.0260 (4)
H10A0.5191−0.01120.14640.031*
C11A0.4392 (2)0.08663 (19)0.25418 (15)0.0243 (4)
H11A0.37740.00430.27410.029*
C12A0.4472 (2)0.22025 (19)0.30064 (14)0.0206 (3)
C13A0.3562 (2)0.2346 (2)0.38233 (16)0.0267 (4)
H13A0.40060.32700.42260.040*
H13B0.34850.16200.42270.040*
H13C0.26100.22410.35430.040*
I1B0.755985 (14)0.434720 (13)0.498669 (9)0.02504 (4)
O1B0.64755 (17)0.24584 (15)0.71745 (14)0.0330 (4)
N1B0.49390 (17)0.36405 (15)0.68719 (11)0.0176 (3)
N2B0.24463 (17)0.28564 (15)0.66686 (11)0.0182 (3)
C1B0.8325 (2)0.53935 (18)0.64543 (13)0.0194 (3)
C2B0.9594 (2)0.65908 (19)0.66103 (14)0.0221 (3)
H2BA1.01220.68760.60820.027*
C3B1.0066 (2)0.7357 (2)0.75644 (14)0.0229 (3)
H3BA1.09230.81510.76770.027*
C4B0.9267 (2)0.6946 (2)0.83480 (14)0.0244 (4)
H4BA0.95780.74740.89830.029*
C5B0.7997 (2)0.57396 (19)0.81873 (14)0.0217 (3)
H5BA0.74610.54640.87140.026*
C6B0.75314 (19)0.49482 (17)0.72370 (12)0.0170 (3)
C7B0.6259 (2)0.35554 (18)0.70882 (13)0.0199 (3)
C8B0.3617 (2)0.24816 (17)0.66336 (12)0.0180 (3)
C9B0.3545 (2)0.10825 (18)0.63597 (14)0.0222 (3)
H9BA0.43810.08590.63360.027*
C10B0.2170 (2)0.0036 (2)0.61241 (15)0.0265 (4)
H10B0.2071−0.09140.59480.032*
C11B0.0950 (2)0.0406 (2)0.61509 (14)0.0257 (4)
H11B0.0027−0.02910.59980.031*
C12B0.1116 (2)0.18363 (19)0.64094 (13)0.0214 (3)
C13B−0.0153 (2)0.2316 (2)0.63969 (16)0.0282 (4)
H13D0.00750.31770.68660.042*
H13E−0.09830.15870.65740.042*
H13F−0.03670.24940.57420.042*
H1NA0.728 (3)0.530 (3)0.2269 (19)0.030 (7)*
H1NB0.485 (3)0.444 (3)0.6892 (19)0.035 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I1A0.02262 (6)0.01832 (5)0.02205 (6)0.00989 (4)0.00152 (4)0.00112 (4)
O1A0.0268 (7)0.0187 (6)0.0190 (6)0.0057 (5)0.0032 (5)−0.0012 (5)
N1A0.0217 (7)0.0118 (5)0.0179 (6)0.0038 (5)0.0027 (5)0.0008 (5)
N2A0.0194 (7)0.0138 (6)0.0189 (6)0.0039 (5)0.0009 (5)0.0029 (5)
C1A0.0212 (8)0.0158 (7)0.0170 (7)0.0062 (6)0.0022 (6)0.0022 (5)
C2A0.0295 (10)0.0152 (7)0.0217 (8)0.0057 (7)0.0019 (7)0.0021 (6)
C3A0.0274 (10)0.0179 (7)0.0231 (8)0.0018 (7)−0.0004 (7)0.0034 (6)
C4A0.0205 (9)0.0229 (8)0.0267 (9)0.0033 (7)0.0022 (7)0.0047 (7)
C5A0.0220 (9)0.0209 (8)0.0259 (8)0.0076 (7)0.0028 (7)0.0051 (7)
C6A0.0202 (8)0.0150 (6)0.0167 (7)0.0055 (6)0.0019 (6)0.0018 (5)
C7A0.0187 (8)0.0151 (6)0.0189 (7)0.0067 (6)0.0026 (6)0.0027 (5)
C8A0.0198 (8)0.0126 (6)0.0180 (7)0.0055 (6)−0.0002 (6)0.0023 (5)
C9A0.0269 (9)0.0141 (7)0.0255 (8)0.0093 (6)0.0020 (7)0.0013 (6)
C10A0.0304 (10)0.0119 (7)0.0344 (10)0.0075 (7)0.0004 (8)0.0004 (7)
C11A0.0249 (9)0.0140 (7)0.0322 (10)0.0045 (6)−0.0003 (7)0.0054 (7)
C12A0.0189 (8)0.0165 (7)0.0260 (8)0.0051 (6)0.0007 (6)0.0065 (6)
C13A0.0278 (10)0.0204 (8)0.0317 (10)0.0062 (7)0.0077 (8)0.0085 (7)
I1B0.02984 (7)0.02357 (6)0.01716 (6)0.00598 (5)0.00087 (4)−0.00172 (4)
O1B0.0255 (7)0.0141 (6)0.0585 (10)0.0062 (5)−0.0030 (7)0.0086 (6)
N1B0.0201 (7)0.0113 (5)0.0198 (6)0.0037 (5)0.0015 (5)0.0023 (5)
N2B0.0196 (7)0.0167 (6)0.0161 (6)0.0040 (5)0.0008 (5)0.0026 (5)
C1B0.0211 (8)0.0171 (7)0.0183 (7)0.0057 (6)0.0016 (6)0.0010 (6)
C2B0.0214 (8)0.0192 (7)0.0219 (8)0.0029 (6)0.0045 (6)0.0016 (6)
C3B0.0209 (9)0.0184 (7)0.0237 (8)0.0017 (6)0.0000 (6)0.0000 (6)
C4B0.0308 (10)0.0172 (7)0.0187 (8)0.0024 (7)−0.0008 (7)−0.0004 (6)
C5B0.0279 (9)0.0169 (7)0.0184 (7)0.0054 (7)0.0037 (6)0.0032 (6)
C6B0.0177 (8)0.0129 (6)0.0192 (7)0.0040 (6)0.0009 (6)0.0026 (5)
C7B0.0221 (8)0.0142 (7)0.0226 (8)0.0053 (6)0.0030 (6)0.0034 (6)
C8B0.0231 (8)0.0128 (6)0.0155 (7)0.0031 (6)0.0006 (6)0.0028 (5)
C9B0.0246 (9)0.0132 (7)0.0253 (8)0.0037 (6)−0.0006 (7)0.0005 (6)
C10B0.0320 (11)0.0139 (7)0.0265 (9)0.0014 (7)−0.0041 (8)0.0014 (6)
C11B0.0241 (9)0.0190 (8)0.0252 (9)−0.0023 (7)−0.0029 (7)0.0036 (7)
C12B0.0219 (9)0.0206 (8)0.0174 (7)0.0023 (6)−0.0002 (6)0.0038 (6)
C13B0.0203 (9)0.0316 (10)0.0284 (9)0.0053 (8)−0.0006 (7)0.0023 (8)
Geometric parameters (Å, °) top
I1A—C1A2.0966 (18)I1B—C1B2.1027 (17)
O1A—C7A1.226 (2)O1B—C7B1.221 (2)
N1A—C7A1.363 (2)N1B—C7B1.354 (2)
N1A—C8A1.414 (2)N1B—C8B1.404 (2)
N1A—H1NA0.83 (3)N1B—H1NB0.84 (3)
N2A—C8A1.342 (2)N2B—C8B1.337 (2)
N2A—C12A1.350 (2)N2B—C12B1.351 (2)
C1A—C2A1.397 (2)C1B—C6B1.388 (2)
C1A—C6A1.398 (2)C1B—C2B1.389 (3)
C2A—C3A1.386 (3)C2B—C3B1.389 (3)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.385 (3)C3B—C4B1.384 (3)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.388 (3)C4B—C5B1.395 (3)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.394 (3)C5B—C6B1.393 (2)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.503 (2)C6B—C7B1.507 (2)
C8A—C9A1.387 (2)C8B—C9B1.393 (2)
C9A—C10A1.384 (3)C9B—C10B1.389 (3)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.379 (3)C10B—C11B1.381 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.391 (3)C11B—C12B1.394 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.492 (3)C12B—C13B1.493 (3)
C13A—H13A0.9600C13B—H13D0.9600
C13A—H13B0.9600C13B—H13E0.9600
C13A—H13C0.9600C13B—H13F0.9600
C7A—N1A—C8A125.92 (15)C7B—N1B—C8B125.89 (15)
C7A—N1A—H1NA120.2 (18)C7B—N1B—H1NB120.7 (19)
C8A—N1A—H1NA113.6 (18)C8B—N1B—H1NB113.4 (19)
C8A—N2A—C12A117.99 (15)C8B—N2B—C12B118.81 (16)
C2A—C1A—C6A120.10 (17)C6B—C1B—C2B121.01 (16)
C2A—C1A—I1A119.55 (13)C6B—C1B—I1B120.61 (13)
C6A—C1A—I1A120.14 (13)C2B—C1B—I1B118.26 (13)
C3A—C2A—C1A119.77 (17)C3B—C2B—C1B119.29 (17)
C3A—C2A—H2AA120.1C3B—C2B—H2BA120.4
C1A—C2A—H2AA120.1C1B—C2B—H2BA120.4
C4A—C3A—C2A120.51 (18)C4B—C3B—C2B120.32 (17)
C4A—C3A—H3AA119.7C4B—C3B—H3BA119.8
C2A—C3A—H3AA119.7C2B—C3B—H3BA119.8
C3A—C4A—C5A119.77 (18)C3B—C4B—C5B120.11 (17)
C3A—C4A—H4AA120.1C3B—C4B—H4BA119.9
C5A—C4A—H4AA120.1C5B—C4B—H4BA119.9
C4A—C5A—C6A120.64 (17)C6B—C5B—C4B119.94 (17)
C4A—C5A—H5AA119.7C6B—C5B—H5BA120.0
C6A—C5A—H5AA119.7C4B—C5B—H5BA120.0
C5A—C6A—C1A119.12 (16)C1B—C6B—C5B119.29 (16)
C5A—C6A—C7A118.07 (15)C1B—C6B—C7B120.77 (15)
C1A—C6A—C7A122.80 (16)C5B—C6B—C7B119.71 (15)
O1A—C7A—N1A124.45 (16)O1B—C7B—N1B125.15 (17)
O1A—C7A—C6A121.70 (16)O1B—C7B—C6B119.13 (17)
N1A—C7A—C6A113.81 (14)N1B—C7B—C6B115.71 (14)
N2A—C8A—C9A123.90 (16)N2B—C8B—C9B123.56 (16)
N2A—C8A—N1A113.34 (14)N2B—C8B—N1B113.63 (14)
C9A—C8A—N1A122.70 (17)C9B—C8B—N1B122.78 (17)
C10A—C9A—C8A117.33 (18)C10B—C9B—C8B117.12 (18)
C10A—C9A—H9AA121.3C10B—C9B—H9BA121.4
C8A—C9A—H9AA121.3C8B—C9B—H9BA121.4
C11A—C10A—C9A119.90 (17)C11B—C10B—C9B120.02 (18)
C11A—C10A—H10A120.1C11B—C10B—H10B120.0
C9A—C10A—H10A120.1C9B—C10B—H10B120.0
C10A—C11A—C12A119.28 (18)C10B—C11B—C12B119.32 (17)
C10A—C11A—H11A120.4C10B—C11B—H11B120.3
C12A—C11A—H11A120.4C12B—C11B—H11B120.3
N2A—C12A—C11A121.60 (18)N2B—C12B—C11B121.10 (18)
N2A—C12A—C13A117.44 (16)N2B—C12B—C13B116.96 (17)
C11A—C12A—C13A120.95 (17)C11B—C12B—C13B121.93 (17)
C12A—C13A—H13A109.5C12B—C13B—H13D109.5
C12A—C13A—H13B109.5C12B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C12A—C13A—H13C109.5C12B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C6A—C1A—C2A—C3A1.4 (3)C6B—C1B—C2B—C3B−0.5 (3)
I1A—C1A—C2A—C3A−173.36 (14)I1B—C1B—C2B—C3B175.59 (14)
C1A—C2A—C3A—C4A1.3 (3)C1B—C2B—C3B—C4B−1.1 (3)
C2A—C3A—C4A—C5A−2.2 (3)C2B—C3B—C4B—C5B1.3 (3)
C3A—C4A—C5A—C6A0.4 (3)C3B—C4B—C5B—C6B0.0 (3)
C4A—C5A—C6A—C1A2.2 (3)C2B—C1B—C6B—C5B1.8 (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—C5A171.60 (13)I1B—C1B—C6B—C7B11.3 (2)
C2A—C1A—C6A—C7A177.67 (16)C4B—C5B—C6B—C1B−1.5 (3)
I1A—C1A—C6A—C7A−7.6 (2)C4B—C5B—C6B—C7B172.96 (17)
C8A—N1A—C7A—O1A0.8 (3)C8B—N1B—C7B—O1B−5.4 (3)
C8A—N1A—C7A—C6A−176.93 (15)C8B—N1B—C7B—C6B175.15 (16)
C5A—C6A—C7A—O1A−77.9 (2)C1B—C6B—C7B—O1B86.5 (2)
C1A—C6A—C7A—O1A101.3 (2)C5B—C6B—C7B—O1B−87.9 (2)
C5A—C6A—C7A—N1A99.94 (19)C1B—C6B—C7B—N1B−94.0 (2)
C1A—C6A—C7A—N1A−80.8 (2)C5B—C6B—C7B—N1B91.6 (2)
C12A—N2A—C8A—C9A0.1 (3)C12B—N2B—C8B—C9B−1.2 (3)
C12A—N2A—C8A—N1A−177.17 (15)C12B—N2B—C8B—N1B177.04 (14)
C7A—N1A—C8A—N2A−153.70 (16)C7B—N1B—C8B—N2B165.94 (16)
C7A—N1A—C8A—C9A29.0 (3)C7B—N1B—C8B—C9B−15.8 (3)
N2A—C8A—C9A—C10A0.0 (3)N2B—C8B—C9B—C10B−0.7 (3)
N1A—C8A—C9A—C10A177.00 (17)N1B—C8B—C9B—C10B−178.83 (17)
C8A—C9A—C10A—C11A−0.2 (3)C8B—C9B—C10B—C11B1.1 (3)
C9A—C10A—C11A—C12A0.2 (3)C9B—C10B—C11B—C12B0.4 (3)
C8A—N2A—C12A—C11A0.0 (3)C8B—N2B—C12B—C11B2.8 (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—C13A179.25 (17)C10B—C11B—C12B—C13B176.50 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···N2Bi0.83 (3)2.14 (3)2.962 (2)172 (3)
N1B—H1NB···N2Ai0.84 (3)2.25 (3)3.079 (2)169 (2)
C9A—H9AA···O1A0.932.402.895 (2)113
C5B—H5BA···O1Aii0.932.583.359 (2)141
C9B—H9BA···O1B0.932.262.825 (3)118
C11A—H11A···O1Biii0.932.483.254 (2)141
C4B—H4BA···Cg1ii0.932.713.565 (2)153
C13A—H13C···Cg2i0.962.853.629 (2)139
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···N2Bi0.83 (3)2.14 (3)2.962 (2)172 (3)
N1B—H1NB···N2Ai0.84 (3)2.25 (3)3.079 (2)169 (2)
C9A—H9AA···O1A0.932.402.895 (2)113
C5B—H5BA···O1Aii0.932.583.359 (2)141
C9B—H9BA···O1B0.932.262.825 (3)118
C11A—H11A···O1Biii0.932.483.254 (2)141
C4B—H4BA···Cg1ii0.932.713.565 (2)153
C13A—H13C···Cg2i0.962.853.629 (2)139
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y, −z+1.
Acknowledgements top

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
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