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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 4| April 2014| Page o445
doi:10.1107/S1600536814005388

N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)benzene­sulfonamide

Venkatesh B. Devaru,a K. S. Katagi,b O. Kotresh,b H. K. Arunkashic and H. C. Devarajegowdad*

aP. G. Department of Physics, LVD College, Raichur 584 103, Karnataka, India, bDepartment of Chemistry, Karnatak Science College, Karnatak University, Dharwad, Karnataka 580 001, India, cDepartment of Physics, Moodlakatte Institute of Technology, Kundapura 576 217, Karnataka, India, and dDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com

(Received 9 March 2014; accepted 10 March 2014; online 15 March 2014)

The asymmetric unit of the title compound, C13H11ClN4O2S, contains two mol­ecules (A and B), in which the dihedral angles between the 1H-imidazo[4,5-c]pyridine system and terminal phenyl ring are 80.83 (10) and 62.34 (1)°. In the crystal, A–B dimers are linked by pairs of N—H⋯N hydrogen bonds, which generate R22(10) loops. The dimers are linked by C—H⋯O and C—H⋯Cl inter­actions, generating a three-dimensional network. Aromatic π–π stacking inter­actions [shortest centroid–centroid distance = 3.5211 (12) Å] are also observed.

CCDC reference: 990803

Related literature

For biological background, see: Kulkarni & Newman (2007[Kulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987-2991.]). For a related structure, see: Kandri Rodi et al. (2013[Kandri Rodi, Y., Haoudi, A., Capet, F., Mazzah, A., Essassi, E. M. & El Ammari, L. (2013). Acta Cryst. E69, o1029-o1030.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11ClN4O2S

  • Mr = 322.77

  • Monoclinic, P 21 /c

  • a = 13.1045 (4) Å

  • b = 14.7259 (5) Å

  • c = 14.6953 (6) Å

  • β = 95.127 (3)°

  • V = 2824.49 (17) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 293 K

  • 0.24 × 0.20 × 0.12 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 16038 measured reflections

  • 4972 independent reflections

  • 3759 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.098

  • S = 1.04

  • 4972 reflections

  • 379 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N7A—H7A⋯N8Bi 0.86 2.25 3.014 (2) 148
N7B—H7B⋯N8Aii 0.86 2.25 3.092 (2) 165
C13A—H13A⋯Cl1Aiii 0.93 2.82 3.620 (3) 144
C20A—H20A⋯O4Aiv 0.93 2.47 3.243 (3) 141
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x, -y+1, -z+1; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 990803

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814005388/hb7208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005388/hb7208Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005388/hb7208Isup3.cml

checkCIF report


Comment top

Imidazo[4,5]pyridine derivatives have been reported as inhibitors of mitogen and stress-activated protein kinases and aurora kinases (Kulkarni & Newman, 2007). As part of our studies of this family of compounds, we now describe the synthesis and structure of the title compound. Its gometrical data are good agreement with those of a related structure (Kandri Rodi et al., 2013)

The asymmetric unit contains two independent molecules A and B respectively are shown in Fig. 1. The 1H-imidazo [4,5-c]pyridine rings system are nearly planar, with a maximum deviations of 0.0284 (19) Å and 0.0061 (19) Å for the atoms C19a and C19b; the dihedral angles between the 1H-imidazo [4,5-c]pyridine (N5a/N6a/N8a/C15a–C20a) & (N5b/N6b/N8b/C15b–C20a) and the terminal benzene (C9a–C14a) & (C9b–C14b) rings are 80.83 (10)° and 62.34 (1)°.

In the crystal, A-B dimers are linked by pairs of N—H···N hydrogen bonds (Table 1), which generate R22(10) loops. The dimers are lined by C—H···O and C—H···Cl interactions to generate a three-dimensional network. Aromatic π–π stacking interactions [shortest centroid–centroid distance = 3.5211 (12) Å] are also observed.

Related literature top

For biological background, see: Kulkarni & Newman (2007). For a related structure, see: Kandri Rodi et al. (2013).

Experimental top

A mixture of 2,4,6-trichloropyridene, methylamine in ethanol was heated and filtered to get pure product. To this sulfuric acid and fuming nitric acid was added, then it was stirred and cooled. A solution of iron powder and ammonium chloride in methanol/water was added and heated. Then triethylorthoformate in ethanol was added and continued the heating. Amination of reaction product was achieved by adding benzophenone imine, potassium carbonate, palladium complex, in dioxane, and then it was heated. The obtained product was dissolved in HCl, stirred, and concentrated in vacuo to give the product. A mixture of obtained product, sodium hydride, 6-chloro-1-methyl-1H-imidazol [4,5-c]pyridin-4-amine and carbonyl/sulfonyl chlorides in tetahydrofuran was stirred and concentrated in vacuo to give the expected products. After completion of each step of the reaction TLC was monitored. The compound is recrystallized by ethanol- chloroform mixture. Colourless needles of the title compound were grown from a mixed solution of ethanol/chloroform (v/v = 2/1) by slow evaporation at room temperature. Yield: 121 mg, 64.84%); mp: 336k; IR cm-1 (KBr) 3435, 1388; Anal. Calcd for C13H11ClN4O2S C, 45.82; H, 2.96; N, 16.44%; Found, C, 45.18; H, 2.92; N, 15.84%.

Refinement top

All H atoms were positioned geometrically, with N—H = 0.86 Å, C—H = 0.93 Å for aromatic H and C—H = 0.96 Å for methyl H, and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as open dashed bonds.
N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)benzenesulfonamide top
Crystal data top
C13H11ClN4O2SF(000) = 1328
Mr = 322.77Dx = 1.518 Mg m−3
Monoclinic, P21/cMelting point: 376 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.1045 (4) ÅCell parameters from 4972 reflections
b = 14.7259 (5) Åθ = 2.8–25.0°
c = 14.6953 (6) ŵ = 0.43 mm−1
β = 95.127 (3)°T = 293 K
V = 2824.49 (17) Å3Plate, colourless
Z = 80.24 × 0.20 × 0.12 mm
Data collection top
Bruker SMART CCD
diffractometer		4972 independent reflections
Radiation source: fine-focus sealed tube3759 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and ϕ scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −15→15
Tmin = 0.770, Tmax = 1.000k = −17→17
16038 measured reflectionsl = −17→17
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) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0619P)2]
where P = (Fo2 + 2Fc2)/3
4972 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C13H11ClN4O2SV = 2824.49 (17) Å3
Mr = 322.77Z = 8
Monoclinic, P21/cMo Kα radiation
a = 13.1045 (4) ŵ = 0.43 mm−1
b = 14.7259 (5) ÅT = 293 K
c = 14.6953 (6) Å0.24 × 0.20 × 0.12 mm
β = 95.127 (3)°
Data collection top
Bruker SMART CCD
diffractometer		4972 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3759 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 1.000Rint = 0.031
16038 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.30 e Å−3
4972 reflectionsΔρmin = −0.31 e Å−3
379 parameters
Special details top

Experimental. IR cm-1 (KBr) 3435, 1388; Anal. Calcd for C13H11ClN4O2S C, 45.82; H, 2.96; N, 16.44%; Found, C, 45.18; H, 2.92; N, 15.84%.

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
xyzUiso*/Ueq
Cl1A0.20678 (5)0.52370 (5)0.40718 (5)0.06025 (19)
Cl1B0.93941 (5)0.41848 (4)0.38570 (5)0.05977 (19)
S2A0.28936 (4)0.22270 (3)0.58582 (4)0.03821 (16)
S2B0.70463 (4)0.13503 (3)0.40663 (4)0.03622 (15)
O3A0.26710 (11)0.21724 (10)0.48964 (11)0.0500 (4)
O3B0.70151 (13)0.19837 (10)0.47946 (11)0.0522 (4)
O4A0.32556 (11)0.14347 (9)0.63449 (13)0.0562 (5)
O4B0.63810 (11)0.05785 (9)0.40271 (11)0.0461 (4)
N5A0.51992 (13)0.58429 (10)0.64248 (12)0.0357 (4)
N5B0.62508 (13)0.45541 (11)0.14780 (12)0.0369 (4)
N6A0.30372 (12)0.41345 (11)0.52175 (12)0.0371 (4)
N6B0.79517 (13)0.30202 (11)0.33564 (12)0.0376 (4)
N7A0.37871 (13)0.29776 (10)0.61344 (13)0.0439 (5)
H7A0.43140.28010.64800.053*
N7B0.67403 (13)0.18711 (11)0.30975 (12)0.0394 (4)
H7B0.63350.15990.26930.047*
N8A0.52770 (13)0.43954 (10)0.69189 (12)0.0360 (4)
N8B0.56595 (12)0.31475 (11)0.16965 (12)0.0364 (4)
C9A0.17905 (15)0.26081 (13)0.63400 (15)0.0354 (5)
C9B0.83185 (15)0.09728 (13)0.40267 (14)0.0354 (5)
C10A0.1679 (2)0.23876 (17)0.72382 (18)0.0609 (7)
H10A0.22020.20940.75930.073*
C10B0.91108 (18)0.14379 (15)0.44983 (16)0.0482 (6)
H10B0.89820.19490.48420.058*
C11A0.0783 (3)0.2610 (2)0.7596 (2)0.0800 (9)
H11A0.06950.24630.82000.096*
C11B1.01033 (19)0.11297 (18)0.44508 (19)0.0594 (7)
H11B1.06450.14330.47710.071*
C12A0.0013 (2)0.30470 (19)0.7073 (2)0.0755 (9)
H12A−0.05960.31870.73210.091*
C12B1.0294 (2)0.03867 (19)0.39389 (19)0.0615 (7)
H12B1.09640.01890.39090.074*
C13A0.01382 (19)0.32755 (18)0.6197 (2)0.0641 (7)
H13A−0.03830.35790.58490.077*
C13B0.9501 (2)−0.00710 (18)0.34674 (18)0.0577 (7)
H13B0.9635−0.05760.31170.069*
C14A0.10334 (16)0.30612 (15)0.58193 (17)0.0458 (6)
H14A0.11220.32220.52190.055*
C14B0.85071 (18)0.02174 (14)0.35123 (16)0.0458 (6)
H14B0.7968−0.00940.31980.055*
C15A0.37606 (14)0.38857 (12)0.58513 (14)0.0318 (4)
C15B0.71004 (15)0.27352 (12)0.28880 (13)0.0321 (5)
C16A0.30231 (16)0.50038 (14)0.49461 (15)0.0378 (5)
C16B0.82753 (15)0.38663 (14)0.32074 (14)0.0376 (5)
C17A0.36691 (15)0.56812 (13)0.52574 (14)0.0356 (5)
H17A0.36170.62740.50410.043*
C17B0.78186 (16)0.44845 (13)0.26077 (14)0.0367 (5)
H17B0.80700.50690.25380.044*
C18A0.44159 (15)0.54000 (12)0.59313 (13)0.0298 (4)
C18B0.69432 (14)0.41563 (13)0.21132 (13)0.0317 (4)
C19A0.44741 (14)0.45033 (12)0.62405 (13)0.0290 (4)
C19B0.65665 (14)0.32852 (12)0.22385 (13)0.0309 (4)
C20A0.56688 (17)0.52153 (13)0.69992 (15)0.0386 (5)
H20A0.62230.53560.74150.046*
C20B0.55180 (16)0.39220 (14)0.12623 (15)0.0401 (5)
H20B0.49590.40290.08400.048*
C21A0.54967 (18)0.67998 (13)0.63396 (16)0.0468 (6)
H21A0.50350.70920.58870.070*
H21B0.61820.68330.61590.070*
H21C0.54670.70990.69170.070*
C21B0.62941 (19)0.54775 (14)0.11289 (18)0.0530 (6)
H21D0.69010.57720.13990.080*
H21E0.57000.58080.12800.080*
H21F0.63100.54610.04770.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0494 (4)0.0661 (4)0.0616 (4)0.0194 (3)−0.0152 (3)0.0047 (3)
Cl1B0.0511 (4)0.0597 (4)0.0645 (4)−0.0155 (3)−0.0170 (3)0.0071 (3)
S2A0.0297 (3)0.0228 (3)0.0614 (4)−0.0001 (2)−0.0003 (2)−0.0053 (2)
S2B0.0421 (3)0.0276 (3)0.0390 (3)−0.0011 (2)0.0037 (2)0.0059 (2)
O3A0.0468 (9)0.0467 (9)0.0569 (11)−0.0055 (7)0.0075 (8)−0.0219 (7)
O3B0.0701 (11)0.0442 (9)0.0439 (10)−0.0004 (8)0.0137 (8)−0.0035 (7)
O4A0.0366 (8)0.0248 (7)0.1057 (14)0.0018 (6)−0.0022 (9)0.0105 (8)
O4B0.0462 (9)0.0344 (8)0.0572 (10)−0.0067 (7)0.0017 (8)0.0130 (7)
N5A0.0416 (10)0.0235 (8)0.0423 (11)−0.0050 (7)0.0055 (8)−0.0038 (7)
N5B0.0379 (10)0.0332 (9)0.0396 (10)0.0005 (8)0.0031 (8)0.0124 (8)
N6A0.0325 (9)0.0314 (9)0.0467 (11)0.0043 (7)−0.0009 (8)−0.0028 (8)
N6B0.0372 (10)0.0336 (9)0.0413 (11)−0.0010 (8)−0.0012 (8)0.0063 (7)
N7A0.0336 (9)0.0254 (9)0.0695 (14)−0.0021 (7)−0.0125 (9)0.0058 (8)
N7B0.0438 (10)0.0285 (9)0.0437 (11)−0.0036 (8)−0.0083 (8)0.0071 (7)
N8A0.0404 (10)0.0297 (9)0.0372 (10)−0.0031 (7)0.0001 (8)−0.0019 (7)
N8B0.0340 (9)0.0362 (9)0.0387 (10)−0.0022 (8)0.0012 (8)0.0083 (8)
C9A0.0366 (11)0.0258 (10)0.0434 (13)−0.0020 (9)0.0016 (10)−0.0051 (9)
C9B0.0400 (11)0.0297 (10)0.0356 (12)−0.0018 (9)−0.0016 (9)0.0104 (9)
C10A0.0735 (18)0.0581 (15)0.0509 (17)0.0107 (14)0.0045 (14)0.0047 (12)
C10B0.0552 (15)0.0413 (12)0.0451 (14)−0.0063 (11)−0.0117 (11)0.0010 (10)
C11A0.112 (3)0.075 (2)0.059 (2)0.0138 (19)0.0413 (19)0.0038 (15)
C11B0.0455 (14)0.0673 (17)0.0621 (18)−0.0127 (13)−0.0139 (12)0.0145 (14)
C12A0.070 (2)0.0649 (18)0.098 (3)0.0096 (15)0.0439 (19)−0.0142 (17)
C12B0.0413 (14)0.0714 (18)0.072 (2)0.0066 (13)0.0078 (13)0.0200 (15)
C13A0.0477 (15)0.0657 (17)0.080 (2)0.0208 (13)0.0115 (14)−0.0072 (15)
C13B0.0556 (16)0.0572 (15)0.0608 (17)0.0078 (13)0.0083 (13)−0.0008 (13)
C14A0.0399 (12)0.0465 (13)0.0508 (15)0.0105 (10)0.0024 (11)−0.0005 (11)
C14B0.0480 (14)0.0406 (12)0.0478 (14)−0.0033 (10)−0.0011 (11)−0.0016 (10)
C15A0.0319 (10)0.0243 (9)0.0393 (12)0.0022 (8)0.0044 (9)−0.0036 (8)
C15B0.0335 (11)0.0271 (10)0.0362 (12)0.0017 (9)0.0061 (9)0.0040 (8)
C16A0.0350 (11)0.0386 (12)0.0394 (13)0.0117 (10)0.0013 (10)−0.0018 (9)
C16B0.0346 (11)0.0399 (12)0.0381 (13)−0.0043 (9)0.0028 (9)0.0002 (9)
C17A0.0401 (11)0.0287 (10)0.0394 (12)0.0078 (9)0.0106 (10)0.0025 (9)
C17B0.0390 (11)0.0317 (10)0.0400 (13)−0.0066 (9)0.0065 (10)0.0053 (9)
C18A0.0345 (11)0.0264 (10)0.0301 (11)0.0021 (8)0.0117 (9)−0.0037 (8)
C18B0.0344 (10)0.0299 (10)0.0318 (11)0.0005 (9)0.0092 (9)0.0065 (8)
C19A0.0310 (10)0.0269 (10)0.0297 (11)0.0007 (8)0.0063 (9)−0.0019 (8)
C19B0.0306 (10)0.0298 (10)0.0330 (12)0.0012 (8)0.0066 (9)0.0024 (8)
C20A0.0412 (12)0.0351 (11)0.0379 (13)−0.0038 (9)−0.0044 (10)−0.0052 (9)
C20B0.0350 (11)0.0429 (12)0.0412 (13)−0.0033 (10)−0.0034 (10)0.0116 (10)
C21A0.0570 (14)0.0276 (11)0.0568 (15)−0.0101 (10)0.0108 (12)−0.0030 (10)
C21B0.0605 (15)0.0373 (12)0.0606 (16)−0.0016 (11)0.0013 (13)0.0230 (11)
Geometric parameters (Å, º) top
Cl1A—C16A1.746 (2)C10B—C11B1.385 (3)
Cl1B—C16B1.741 (2)C10B—H10B0.9300
S2A—O3A1.4198 (17)C11A—C12A1.373 (4)
S2A—O4A1.4273 (15)C11A—H11A0.9300
S2A—N7A1.6347 (17)C11B—C12B1.363 (4)
S2A—C9A1.757 (2)C11B—H11B0.9300
S2B—O3B1.4230 (16)C12A—C13A1.354 (4)
S2B—O4B1.4305 (14)C12A—H12A0.9300
S2B—N7B1.6352 (17)C12B—C13B1.373 (4)
S2B—C9B1.763 (2)C12B—H12B0.9300
N5A—C20A1.361 (3)C13A—C14A1.379 (3)
N5A—C18A1.368 (2)C13A—H13A0.9300
N5A—C21A1.470 (2)C13B—C14B1.377 (3)
N5B—C20B1.354 (3)C13B—H13B0.9300
N5B—C18B1.374 (2)C14A—H14A0.9300
N5B—C21B1.456 (2)C14B—H14B0.9300
N6A—C15A1.320 (2)C15A—C19A1.390 (3)
N6A—C16A1.341 (3)C15B—C19B1.392 (3)
N6B—C15B1.326 (3)C16A—C17A1.361 (3)
N6B—C16B1.340 (2)C16B—C17B1.367 (3)
N7A—C15A1.400 (2)C17A—C18A1.392 (3)
N7A—H7A0.8600C17A—H17A0.9300
N7B—C15B1.401 (2)C17B—C18B1.389 (3)
N7B—H7B0.8600C17B—H17B0.9300
N8A—C20A1.313 (2)C18A—C19A1.396 (3)
N8A—C19A1.392 (3)C18B—C19B1.393 (3)
N8B—C20B1.312 (2)C20A—H20A0.9300
N8B—C19B1.385 (2)C20B—H20B0.9300
C9A—C14A1.371 (3)C21A—H21A0.9600
C9A—C10A1.380 (3)C21A—H21B0.9600
C9B—C10B1.378 (3)C21A—H21C0.9600
C9B—C14B1.380 (3)C21B—H21D0.9600
C10A—C11A1.369 (4)C21B—H21E0.9600
C10A—H10A0.9300C21B—H21F0.9600
O3A—S2A—O4A118.82 (10)C12B—C13B—H13B120.0
O3A—S2A—N7A111.37 (10)C14B—C13B—H13B120.0
O4A—S2A—N7A103.28 (9)C9A—C14A—C13A119.1 (2)
O3A—S2A—C9A108.41 (10)C9A—C14A—H14A120.5
O4A—S2A—C9A107.92 (10)C13A—C14A—H14A120.5
N7A—S2A—C9A106.31 (9)C9B—C14B—C13B119.4 (2)
O3B—S2B—O4B119.51 (9)C9B—C14B—H14B120.3
O3B—S2B—N7B109.03 (9)C13B—C14B—H14B120.3
O4B—S2B—N7B103.68 (9)N6A—C15A—C19A121.52 (17)
O3B—S2B—C9B108.80 (10)N6A—C15A—N7A118.16 (17)
O4B—S2B—C9B108.84 (9)C19A—C15A—N7A120.32 (18)
N7B—S2B—C9B106.16 (9)N6B—C15B—C19B121.33 (17)
C20A—N5A—C18A106.34 (15)N6B—C15B—N7B117.25 (17)
C20A—N5A—C21A126.50 (18)C19B—C15B—N7B121.38 (18)
C18A—N5A—C21A127.14 (18)N6A—C16A—C17A127.47 (19)
C20B—N5B—C18B106.11 (15)N6A—C16A—Cl1A113.37 (16)
C20B—N5B—C21B127.47 (19)C17A—C16A—Cl1A119.14 (16)
C18B—N5B—C21B126.40 (18)N6B—C16B—C17B126.69 (19)
C15A—N6A—C16A117.71 (17)N6B—C16B—Cl1B115.09 (16)
C15B—N6B—C16B118.25 (18)C17B—C16B—Cl1B118.22 (15)
C15A—N7A—S2A125.03 (15)C16A—C17A—C18A113.45 (18)
C15A—N7A—H7A117.5C16A—C17A—H17A123.3
S2A—N7A—H7A117.5C18A—C17A—H17A123.3
C15B—N7B—S2B123.79 (15)C16B—C17B—C18B113.53 (18)
C15B—N7B—H7B118.1C16B—C17B—H17B123.2
S2B—N7B—H7B118.1C18B—C17B—H17B123.2
C20A—N8A—C19A102.94 (16)N5A—C18A—C17A133.00 (17)
C20B—N8B—C19B103.25 (16)N5A—C18A—C19A105.18 (17)
C14A—C9A—C10A121.0 (2)C17A—C18A—C19A121.82 (18)
C14A—C9A—S2A120.72 (17)N5B—C18B—C17B132.22 (17)
C10A—C9A—S2A118.14 (18)N5B—C18B—C19B105.20 (17)
C10B—C9B—C14B120.8 (2)C17B—C18B—C19B122.51 (18)
C10B—C9B—S2B119.93 (17)N8A—C19A—C15A131.09 (17)
C14B—C9B—S2B119.24 (16)N8A—C19A—C18A110.89 (17)
C11A—C10A—C9A118.7 (3)C15A—C19A—C18A118.02 (18)
C11A—C10A—H10A120.7N8B—C19B—C18B110.79 (17)
C9A—C10A—H10A120.7N8B—C19B—C15B131.45 (17)
C9B—C10B—C11B118.7 (2)C18B—C19B—C15B117.66 (18)
C9B—C10B—H10B120.6N8A—C20A—N5A114.65 (19)
C11B—C10B—H10B120.6N8A—C20A—H20A122.7
C10A—C11A—C12A120.6 (3)N5A—C20A—H20A122.7
C10A—C11A—H11A119.7N8B—C20B—N5B114.65 (18)
C12A—C11A—H11A119.7N8B—C20B—H20B122.7
C12B—C11B—C10B120.6 (2)N5B—C20B—H20B122.7
C12B—C11B—H11B119.7N5A—C21A—H21A109.5
C10B—C11B—H11B119.7N5A—C21A—H21B109.5
C13A—C12A—C11A120.2 (2)H21A—C21A—H21B109.5
C13A—C12A—H12A119.9N5A—C21A—H21C109.5
C11A—C12A—H12A119.9H21A—C21A—H21C109.5
C11B—C12B—C13B120.3 (2)H21B—C21A—H21C109.5
C11B—C12B—H12B119.8N5B—C21B—H21D109.5
C13B—C12B—H12B119.8N5B—C21B—H21E109.5
C12A—C13A—C14A120.4 (3)H21D—C21B—H21E109.5
C12A—C13A—H13A119.8N5B—C21B—H21F109.5
C14A—C13A—H13A119.8H21D—C21B—H21F109.5
C12B—C13B—C14B120.0 (2)H21E—C21B—H21F109.5
O3A—S2A—N7A—C15A54.0 (2)C15B—N6B—C16B—C17B−0.4 (3)
O4A—S2A—N7A—C15A−177.38 (17)C15B—N6B—C16B—Cl1B179.63 (15)
C9A—S2A—N7A—C15A−63.9 (2)N6A—C16A—C17A—C18A0.2 (3)
O3B—S2B—N7B—C15B42.58 (18)Cl1A—C16A—C17A—C18A−177.92 (14)
O4B—S2B—N7B—C15B170.92 (16)N6B—C16B—C17B—C18B−1.1 (3)
C9B—S2B—N7B—C15B−74.47 (18)Cl1B—C16B—C17B—C18B178.91 (15)
O3A—S2A—C9A—C14A−20.6 (2)C20A—N5A—C18A—C17A179.0 (2)
O4A—S2A—C9A—C14A−150.49 (17)C21A—N5A—C18A—C17A−2.4 (3)
N7A—S2A—C9A—C14A99.25 (18)C20A—N5A—C18A—C19A−0.8 (2)
O3A—S2A—C9A—C10A155.31 (17)C21A—N5A—C18A—C19A177.74 (17)
O4A—S2A—C9A—C10A25.4 (2)C16A—C17A—C18A—N5A−179.73 (19)
N7A—S2A—C9A—C10A−84.85 (19)C16A—C17A—C18A—C19A0.1 (3)
O3B—S2B—C9B—C10B−14.6 (2)C20B—N5B—C18B—C17B−176.7 (2)
O4B—S2B—C9B—C10B−146.40 (17)C21B—N5B—C18B—C17B2.1 (3)
N7B—S2B—C9B—C10B102.56 (18)C20B—N5B—C18B—C19B0.0 (2)
O3B—S2B—C9B—C14B166.09 (16)C21B—N5B—C18B—C19B178.77 (19)
O4B—S2B—C9B—C14B34.3 (2)C16B—C17B—C18B—N5B177.4 (2)
N7B—S2B—C9B—C14B−76.70 (18)C16B—C17B—C18B—C19B1.2 (3)
C14A—C9A—C10A—C11A1.7 (4)C20A—N8A—C19A—C15A−179.5 (2)
S2A—C9A—C10A—C11A−174.2 (2)C20A—N8A—C19A—C18A0.2 (2)
C14B—C9B—C10B—C11B−0.4 (3)N6A—C15A—C19A—N8A178.71 (19)
S2B—C9B—C10B—C11B−179.61 (18)N7A—C15A—C19A—N8A−0.5 (3)
C9A—C10A—C11A—C12A−0.3 (4)N6A—C15A—C19A—C18A−1.0 (3)
C9B—C10B—C11B—C12B0.7 (4)N7A—C15A—C19A—C18A179.78 (17)
C10A—C11A—C12A—C13A−0.9 (5)N5A—C18A—C19A—N8A0.4 (2)
C10B—C11B—C12B—C13B−0.5 (4)C17A—C18A—C19A—N8A−179.47 (17)
C11A—C12A—C13A—C14A0.8 (4)N5A—C18A—C19A—C15A−179.87 (16)
C11B—C12B—C13B—C14B−0.2 (4)C17A—C18A—C19A—C15A0.3 (3)
C10A—C9A—C14A—C13A−1.7 (3)C20B—N8B—C19B—C18B0.4 (2)
S2A—C9A—C14A—C13A174.03 (18)C20B—N8B—C19B—C15B176.6 (2)
C12A—C13A—C14A—C9A0.5 (4)N5B—C18B—C19B—N8B−0.3 (2)
C10B—C9B—C14B—C13B−0.3 (3)C17B—C18B—C19B—N8B176.86 (18)
S2B—C9B—C14B—C13B178.94 (18)N5B—C18B—C19B—C15B−177.09 (17)
C12B—C13B—C14B—C9B0.6 (4)C17B—C18B—C19B—C15B0.0 (3)
C16A—N6A—C15A—C19A1.2 (3)N6B—C15B—C19B—N8B−177.66 (19)
C16A—N6A—C15A—N7A−179.50 (18)N7B—C15B—C19B—N8B0.0 (3)
S2A—N7A—C15A—N6A−9.7 (3)N6B—C15B—C19B—C18B−1.6 (3)
S2A—N7A—C15A—C19A169.53 (15)N7B—C15B—C19B—C18B176.01 (17)
C16B—N6B—C15B—C19B1.8 (3)C19A—N8A—C20A—N5A−0.8 (2)
C16B—N6B—C15B—N7B−175.93 (17)C18A—N5A—C20A—N8A1.1 (2)
S2B—N7B—C15B—N6B21.4 (2)C21A—N5A—C20A—N8A−177.51 (18)
S2B—N7B—C15B—C19B−156.28 (15)C19B—N8B—C20B—N5B−0.4 (2)
C15A—N6A—C16A—C17A−0.9 (3)C18B—N5B—C20B—N8B0.2 (2)
C15A—N6A—C16A—Cl1A177.34 (15)C21B—N5B—C20B—N8B−178.51 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7A—H7A···N8Bi0.862.253.014 (2)148
N7B—H7B···N8Aii0.862.253.092 (2)165
C13A—H13A···Cl1Aiii0.932.823.620 (3)144
C20A—H20A···O4Aiv0.932.473.243 (3)141
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+1, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7A—H7A···N8Bi0.862.253.014 (2)148
N7B—H7B···N8Aii0.862.253.092 (2)165
C13A—H13A···Cl1Aiii0.932.823.620 (3)144
C20A—H20A···O4Aiv0.932.473.243 (3)141
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+1, y+1/2, −z+3/2.
 

Acknowledgements

We thank the DST, India for funding under DST–FIST (Level II) for the X-ray diffraction facility at SSCU, IISc, Bangalore.

References

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 First citationKandri Rodi, Y., Haoudi, A., Capet, F., Mazzah, A., Essassi, E. M. & El Ammari, L. (2013). Acta Cryst. E69, o1029–o1030.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationKulkarni, S. S. & Newman, A. H. (2007). Bioorg. Med. Chem. Lett. 17, 2987–2991.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 70| Part 4| April 2014| Page o445
doi:10.1107/S1600536814005388
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