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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 9| September 2013| Pages o1411-o1412

Ethyl 2-amino-4-(4-methyl-1,3-thia­zol-5-yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxyl­ate

aDepartment of Chemistry, Madras Christian College, Tambaram, Chennai 600 059, Tamil Nadu, India, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, Tamil Nadu, India
*Correspondence e-mail: rjkmcc@yahoo.com

(Received 20 July 2013; accepted 3 August 2013; online 10 August 2013)

There are two independent mol­ecules in the asymmetric unit of the title compound, C19H16N2O5S, in which the thia­zole rings make dihedral angles of 80.89 (11) and 84.81 (11)° with the pyrano[3,2-c]chromene ring systems. An intra­molecular N—H⋯O hydrogen bond involving the amino group occurs in each independent mol­ecule. In the crystal, the amino groups are involved in N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

Similar conformations were observed in the structures of ethyl 2-amino-5-oxo-4-(p-tol­yl)-4H,5H-pyrano[3,2-c]chromene-8-carboxyl­ate (Wang et al., 2004[Wang, J., Shi, D. & Wang, X. (2004). Acta Cryst. E60, o1725-o1727.]) and ethyl 2-amino-4-(2,4-di­chloro­phen­yl)-4H-benzo[f]chromene-3-carboxyl­ate (Shi et al., 2003[Shi, D.-Q., Wang, J., Wang, X., Zhuang, Q. & Yu, K. (2003). Acta Cryst. E59, o1733-o1734.]). For applications of 4H-chromene and its derivatives, see: Jeso & Nicolaou (2009[Jeso, V. & Nicolaou, K. C. (2009). Tetrahedron Lett. 50, 1161-1163.]); Alvey et al. (2008[Alvey, L., Prado, S., Huteau, V., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2008). Bioorg. Med. Chem. 16, 8264-8272.], 2009[Alvey, L., Prado, S., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2009). Eur. J. Med. Chem. 44, 2497-2505.]); Bedair et al. (2001[Bedair, A. H., Emam, H. A., El-Hady, N. A., Ahmed, K. A. R. & El-Agrody, A. M. (2001). Il Farmaco, 56, 965-973.]); El-Agrody et al. (2002[El-Agrody, A. M., Eid, F. A., Emam, H. A., Mohamed, H. M. & Bedair, A. H. (2002). Z. Naturforsch. Teil B, 57, 579-585.], 2011[El-Agrody, A. M., Sabry, N. M. & Motlaq, S. S. (2011). J. Chem. Res. 35, 77-83.]); Abd-El-Aziz et al. (2004[Abd-El-Aziz, A. S., El-Agrody, A. M., Bedair, A. H., Corkery, T. C. & Ata, A. (2004). Heterocycles, 63, 1793-1812.]); Sabry et al. (2011[Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765-772.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16N2O5S

  • Mr = 384.41

  • Monoclinic, P 21 /n

  • a = 15.6232 (10) Å

  • b = 15.0696 (9) Å

  • c = 15.9063 (11) Å

  • β = 98.873 (2)°

  • V = 3700.1 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 298 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.970

  • 18921 measured reflections

  • 6130 independent reflections

  • 3527 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.145

  • S = 1.03

  • 6130 reflections

  • 491 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1B⋯O4 0.86 2.11 2.698 (3) 125
N1—H1B⋯N2Ai 0.86 2.49 3.152 (3) 135
N1—H1C⋯N2ii 0.86 2.27 3.116 (4) 167
N1A—H1A2⋯N2Aiii 0.86 2.13 2.988 (4) 174
N1A—H1A1⋯O4A 0.86 2.09 2.690 (3) 126
N1A—H1A1⋯O4ii 0.86 2.52 2.936 (3) 111
Symmetry codes: (i) x, y, z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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


Comment top

Thiazoles are important class of heterocyclic compounds, found in many potent biologically active molecules such as Sulfathiazol (antimicrobial drug), Ritonavir (antiretroviral drug) and Tiazofurin (antineoplastic drug) similarly 4-Hydroxycoumarin forms the nucleus of many natural products and drugs and is also a key intermediate for the widely used oral anticoagulants and rodenticides. There is interest in fused pyranochromenes because chromene derivatives (Jeso & Nicolaou, 2009; Alvey et al., 2008, 2009); can be used as immunomodulators and for the treatment of different diseases of connective tissues, diabetes, anti-cancer and for applications of 4H-chromene and its derivatives, (Bedair et al. (2001); El-Agrody et al. (2002, 2011); Abd-El-Aziz et al. (2004); Sabry et al. (2011)). We present here the synthesis and crystal structure of the title compound,(I). The molecule is being assessed for biological activity. In the title compound,C19H16N2O5, there are two independent molecules in the asymmetric unit. The thiazole rings make a dihedral angle with 4H, 5H-pyrano[3,2-c]chromene ring system of 80.89 (11) and 84.81 (11)°. In the crystal structure, the amino groups are involved in both intra-and intermolecular N—H···O and N—H···N hydrogen bonds respectively, table1.

Related literature top

Similar conformations were observed in the structures of ethyl 2-amino-5-oxo-4-(p-tolyl)-4H,5H-pyrano[3,2-c]chromene-8-carboxylate (Wang et al., 2004) and ethyl 2-amino-4-(2,4-dichlorophenyl)-4H-benzo[f]chromene-3-carboxylate (Shi et al., 2003). For applications of 4H-chromene and its derivatives, see: Jeso & Nicolaou (2009); Alvey et al. (2008, 2009); Bedair et al. (2001); El-Agrody et al. (2002, 2011); Abd-El-Aziz et al. (2004); Sabry et al. (2011).

Experimental top

A solution of heteroaromatic aldehyde (1 mmol), 1.2 mmol of alkylnitriles, 4-Hydroxy coumarins(1.1 mmol) and catalytic amount of silver trifluoromethanesulfonate (5 mol %) in 10 mL of ethanol and the reaction mixture refluxed for two hours. After completion of the reaction, which was monitored by TLC, the reaction mixture was cooled to room temperature and kept overnight in a refrigerator. The solid mass separated out was filtered and purified by column chromatography using n-Hexane: Ethylacetate mixture in the ratio (3:2). The crude product formed was recrystallized in ethanol.

Refinement top

All hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms with aromatic C—H = 0.93 Å, methine C—H = 0.98 Å me thylene C—H = 0.97 Å and methyl C—H = 0.96 Å. The displacement parameters were set for phenyl H atoms at Uiso(H) = 1.2Ueq(C,N) and for methine,methylene and methyl H atoms at Uiso(H) =1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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. ORTEP of the molecule with atoms represented as 30% probability ellipsoids.
Ethyl 2-amino-4-(4-methyl-1,3-thiazol-5-yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate top
Crystal data top
C19H16N2O5SF(000) = 1600
Mr = 384.41Dx = 1.380 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.6232 (10) ÅCell parameters from 3286 reflections
b = 15.0696 (9) Åθ = 2.4–21.4°
c = 15.9063 (11) ŵ = 0.21 mm1
β = 98.873 (2)°T = 298 K
V = 3700.1 (4) Å3Rectangular, yellow
Z = 80.35 × 0.25 × 0.15 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
phi and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1318
Tmin = 0.931, Tmax = 0.970k = 1614
18921 measured reflectionsl = 1818
6130 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0714P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
6130 reflectionsΔρmax = 0.20 e Å3
491 parametersΔρmin = 0.29 e Å3
Crystal data top
C19H16N2O5SV = 3700.1 (4) Å3
Mr = 384.41Z = 8
Monoclinic, P21/nMo Kα radiation
a = 15.6232 (10) ŵ = 0.21 mm1
b = 15.0696 (9) ÅT = 298 K
c = 15.9063 (11) Å0.35 × 0.25 × 0.15 mm
β = 98.873 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6130 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
3527 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.970Rint = 0.042
18921 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å3
6130 reflectionsΔρmin = 0.29 e Å3
491 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3585 (2)0.4642 (2)0.70875 (18)0.0433 (8)
H10.32090.46860.74850.052*
C20.3845 (2)0.5395 (2)0.67213 (19)0.0500 (9)
H20.36390.59460.68620.060*
C30.4417 (2)0.5334 (2)0.61380 (19)0.0510 (9)
H30.45990.58470.58940.061*
C40.4715 (2)0.4524 (2)0.59173 (18)0.0483 (9)
H40.50980.44840.55260.058*
C50.44379 (18)0.3771 (2)0.62839 (17)0.0360 (7)
C60.38746 (18)0.38107 (19)0.68747 (16)0.0332 (7)
C70.45393 (19)0.2176 (2)0.63881 (17)0.0380 (7)
C80.39486 (18)0.22000 (19)0.69980 (16)0.0334 (7)
C90.36581 (18)0.2982 (2)0.72308 (16)0.0343 (7)
C100.37038 (19)0.13370 (18)0.73763 (17)0.0357 (7)
H100.42350.09870.75230.043*
C110.33538 (19)0.15276 (19)0.81953 (17)0.0357 (7)
C120.30737 (19)0.2347 (2)0.83743 (17)0.0374 (7)
C130.30880 (19)0.08051 (18)0.67326 (17)0.0359 (7)
C140.3214 (2)0.0002 (2)0.63837 (19)0.0453 (8)
C150.1869 (3)0.0224 (2)0.5769 (2)0.0572 (10)
H150.13430.01160.54220.069*
C160.3354 (2)0.0848 (2)0.88338 (19)0.0449 (8)
C170.3666 (4)0.0665 (3)0.9178 (2)0.1105 (19)
H17A0.41280.05880.96560.133*
H17B0.31200.06760.93970.133*
C180.3781 (3)0.1472 (3)0.8767 (3)0.1049 (16)
H18A0.33760.15070.82480.157*
H18B0.36840.19570.91320.157*
H18C0.43610.15030.86390.157*
C190.4028 (3)0.0539 (2)0.6518 (2)0.0752 (12)
H19A0.44590.02380.69120.113*
H19B0.42350.06130.59850.113*
H19C0.39120.11100.67430.113*
C1A0.3840 (2)0.7211 (2)0.20315 (18)0.0483 (9)
H1A0.35060.73240.24560.058*
C2A0.4120 (2)0.7901 (2)0.1583 (2)0.0562 (9)
H2A0.39750.84810.17030.067*
C3A0.4616 (2)0.7739 (3)0.0952 (2)0.0599 (10)
H3A0.48040.82120.06530.072*
C4A0.4834 (2)0.6890 (3)0.07611 (19)0.0579 (10)
H4A0.51650.67830.03330.069*
C5A0.4555 (2)0.6196 (2)0.12157 (18)0.0450 (8)
C6A0.40567 (19)0.6337 (2)0.18521 (17)0.0395 (8)
C7A0.4552 (2)0.4608 (2)0.14276 (19)0.0480 (9)
C8A0.40041 (19)0.4741 (2)0.20780 (17)0.0392 (8)
C9A0.37984 (19)0.5566 (2)0.22772 (17)0.0392 (8)
C10A0.3687 (2)0.39270 (19)0.24977 (18)0.0415 (8)
H10A0.41820.35320.26650.050*
C11A0.33376 (19)0.4208 (2)0.32967 (17)0.0382 (8)
C12A0.3164 (2)0.5074 (2)0.34506 (18)0.0413 (8)
C13A0.30238 (19)0.34343 (19)0.18653 (18)0.0394 (8)
C14A0.1765 (2)0.2990 (2)0.08913 (18)0.0489 (9)
H14A0.12330.29330.05420.059*
C15A0.3095 (2)0.2642 (2)0.14837 (19)0.0449 (8)
C16A0.3177 (2)0.3561 (2)0.3915 (2)0.0472 (8)
C17A0.3257 (3)0.2039 (2)0.4303 (2)0.0780 (13)
H17C0.26410.19870.43190.094*
H17D0.35460.21820.48710.094*
C18A0.3591 (4)0.1201 (3)0.4024 (3)0.132 (2)
H18D0.33150.10710.34550.198*
H18E0.34710.07330.43990.198*
H18F0.42050.12480.40340.198*
C19A0.3861 (2)0.2038 (2)0.1600 (2)0.0764 (12)
H20X0.40440.19340.10590.115*
H19X0.37060.14840.18340.115*
H21X0.43250.23070.19810.115*
N10.27345 (17)0.26186 (17)0.90444 (15)0.0552 (8)
H1B0.26680.22500.94420.066*
H1C0.25810.31640.90820.066*
N20.2506 (2)0.03345 (19)0.58422 (16)0.0541 (7)
N1A0.28373 (18)0.54145 (17)0.40989 (15)0.0577 (8)
H1A10.27060.50730.44930.069*
H1A20.27560.59780.41260.069*
N2A0.23690 (18)0.23858 (17)0.09262 (15)0.0473 (7)
O10.47619 (13)0.29715 (14)0.60465 (11)0.0430 (5)
O20.48555 (14)0.15115 (14)0.61402 (13)0.0505 (6)
O30.31266 (13)0.30626 (12)0.78376 (12)0.0434 (5)
O40.31017 (17)0.09227 (14)0.95117 (14)0.0642 (7)
O50.36704 (17)0.00778 (15)0.85867 (13)0.0666 (7)
O1A0.47929 (14)0.53504 (16)0.10116 (12)0.0537 (6)
O2A0.48122 (15)0.39022 (17)0.12158 (15)0.0656 (7)
O3A0.33117 (14)0.57478 (12)0.29067 (12)0.0453 (6)
O4A0.28704 (17)0.36983 (14)0.45668 (14)0.0619 (7)
O5A0.34104 (15)0.27344 (14)0.37173 (13)0.0590 (6)
S10.20650 (6)0.11782 (6)0.63551 (5)0.0507 (3)
S1A0.20197 (5)0.38856 (5)0.15289 (5)0.0484 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.049 (2)0.042 (2)0.0415 (18)0.0003 (16)0.0142 (15)0.0060 (16)
C20.060 (2)0.037 (2)0.053 (2)0.0018 (17)0.0116 (18)0.0078 (16)
C30.064 (2)0.044 (2)0.0453 (19)0.0088 (18)0.0071 (17)0.0127 (16)
C40.057 (2)0.054 (2)0.0367 (18)0.0094 (19)0.0154 (16)0.0099 (16)
C50.0385 (18)0.038 (2)0.0321 (16)0.0052 (15)0.0058 (14)0.0017 (14)
C60.0364 (17)0.0336 (19)0.0297 (15)0.0022 (15)0.0054 (13)0.0035 (13)
C70.0371 (18)0.042 (2)0.0356 (17)0.0046 (16)0.0073 (14)0.0029 (15)
C80.0348 (18)0.0332 (19)0.0331 (16)0.0007 (14)0.0086 (14)0.0013 (13)
C90.0341 (18)0.042 (2)0.0287 (15)0.0054 (15)0.0091 (13)0.0040 (14)
C100.0395 (18)0.0319 (18)0.0375 (16)0.0021 (14)0.0117 (14)0.0029 (13)
C110.0462 (19)0.0272 (19)0.0343 (16)0.0032 (15)0.0087 (14)0.0055 (13)
C120.0440 (19)0.036 (2)0.0338 (16)0.0011 (15)0.0126 (14)0.0060 (14)
C130.0435 (19)0.0272 (18)0.0389 (17)0.0025 (14)0.0122 (14)0.0020 (13)
C140.054 (2)0.040 (2)0.0455 (19)0.0012 (17)0.0175 (17)0.0026 (15)
C150.064 (3)0.059 (3)0.047 (2)0.018 (2)0.0033 (18)0.0006 (17)
C160.062 (2)0.033 (2)0.0415 (19)0.0010 (17)0.0118 (17)0.0003 (16)
C170.229 (6)0.041 (3)0.066 (3)0.024 (3)0.037 (3)0.024 (2)
C180.152 (5)0.048 (3)0.103 (3)0.003 (3)0.018 (3)0.014 (2)
C190.078 (3)0.054 (3)0.097 (3)0.011 (2)0.024 (2)0.020 (2)
C1A0.055 (2)0.048 (2)0.0406 (18)0.0030 (18)0.0042 (16)0.0028 (16)
C2A0.060 (2)0.052 (2)0.053 (2)0.0077 (19)0.0011 (19)0.0086 (18)
C3A0.066 (3)0.064 (3)0.045 (2)0.020 (2)0.0038 (19)0.0170 (19)
C4A0.059 (2)0.080 (3)0.0356 (18)0.016 (2)0.0104 (16)0.0028 (19)
C5A0.044 (2)0.055 (2)0.0348 (17)0.0073 (18)0.0022 (15)0.0017 (16)
C6A0.0421 (19)0.047 (2)0.0291 (16)0.0042 (16)0.0041 (14)0.0013 (14)
C7A0.045 (2)0.057 (3)0.0427 (19)0.0045 (19)0.0114 (16)0.0123 (18)
C8A0.0362 (19)0.044 (2)0.0379 (17)0.0043 (15)0.0094 (14)0.0087 (15)
C9A0.0403 (19)0.045 (2)0.0329 (17)0.0008 (16)0.0064 (14)0.0064 (15)
C10A0.0434 (19)0.038 (2)0.0440 (18)0.0058 (16)0.0110 (15)0.0054 (15)
C11A0.045 (2)0.031 (2)0.0392 (17)0.0036 (15)0.0090 (15)0.0037 (14)
C12A0.048 (2)0.041 (2)0.0375 (18)0.0030 (16)0.0149 (15)0.0013 (15)
C13A0.042 (2)0.0343 (19)0.0441 (18)0.0028 (15)0.0128 (15)0.0048 (15)
C14A0.052 (2)0.053 (2)0.0424 (19)0.0091 (19)0.0088 (16)0.0053 (16)
C15A0.047 (2)0.039 (2)0.0494 (19)0.0021 (17)0.0112 (17)0.0092 (16)
C16A0.056 (2)0.037 (2)0.048 (2)0.0064 (17)0.0073 (17)0.0043 (16)
C17A0.114 (4)0.051 (3)0.060 (2)0.009 (2)0.014 (2)0.015 (2)
C18A0.224 (7)0.041 (3)0.134 (4)0.026 (3)0.038 (4)0.008 (3)
C19A0.070 (3)0.059 (3)0.097 (3)0.019 (2)0.002 (2)0.029 (2)
N10.088 (2)0.0408 (17)0.0458 (16)0.0083 (15)0.0388 (16)0.0078 (13)
N20.066 (2)0.0483 (19)0.0489 (17)0.0119 (17)0.0105 (15)0.0081 (14)
N1A0.090 (2)0.0409 (17)0.0509 (17)0.0079 (15)0.0370 (16)0.0016 (13)
N2A0.0552 (19)0.0448 (18)0.0449 (16)0.0033 (15)0.0168 (14)0.0096 (13)
O10.0501 (14)0.0427 (14)0.0400 (12)0.0067 (11)0.0194 (10)0.0034 (10)
O20.0545 (15)0.0446 (15)0.0574 (14)0.0001 (12)0.0247 (12)0.0051 (11)
O30.0574 (14)0.0333 (12)0.0454 (12)0.0046 (10)0.0272 (11)0.0093 (10)
O40.110 (2)0.0454 (14)0.0434 (13)0.0031 (14)0.0307 (14)0.0088 (11)
O50.114 (2)0.0379 (15)0.0519 (14)0.0119 (14)0.0255 (14)0.0121 (11)
O1A0.0576 (15)0.0633 (17)0.0442 (13)0.0056 (13)0.0208 (11)0.0059 (12)
O2A0.0713 (18)0.0610 (17)0.0717 (16)0.0015 (14)0.0345 (14)0.0232 (13)
O3A0.0601 (15)0.0358 (13)0.0453 (12)0.0057 (11)0.0251 (11)0.0003 (10)
O4A0.0930 (19)0.0478 (15)0.0487 (14)0.0059 (13)0.0231 (13)0.0018 (11)
O5A0.0852 (19)0.0352 (15)0.0562 (14)0.0033 (13)0.0094 (13)0.0022 (11)
S10.0503 (6)0.0434 (6)0.0562 (5)0.0018 (4)0.0015 (4)0.0026 (4)
S1A0.0482 (5)0.0384 (5)0.0594 (5)0.0043 (4)0.0107 (4)0.0031 (4)
Geometric parameters (Å, º) top
C1—C21.365 (4)C1A—H1A0.9300
C1—C61.392 (4)C2A—C3A1.380 (4)
C1—H10.9300C2A—H2A0.9300
C2—C31.387 (4)C3A—C4A1.370 (5)
C2—H20.9300C3A—H3A0.9300
C3—C41.372 (4)C4A—C5A1.380 (4)
C3—H30.9300C4A—H4A0.9300
C4—C51.375 (4)C5A—O1A1.380 (4)
C4—H40.9300C5A—C6A1.385 (4)
C5—O11.382 (3)C6A—C9A1.433 (4)
C5—C61.384 (4)C7A—O2A1.205 (4)
C6—C91.433 (4)C7A—O1A1.381 (4)
C7—O21.209 (3)C7A—C8A1.455 (4)
C7—O11.383 (3)C8A—C9A1.335 (4)
C7—C81.439 (4)C8A—C10A1.516 (4)
C8—C91.336 (4)C9A—O3A1.375 (3)
C8—C101.507 (4)C10A—C11A1.518 (4)
C9—O31.372 (3)C10A—C13A1.521 (4)
C10—C111.516 (4)C10A—H10A0.9800
C10—C131.521 (4)C11A—C12A1.363 (4)
C10—H100.9800C11A—C16A1.434 (4)
C11—C121.355 (4)C12A—N1A1.323 (3)
C11—C161.442 (4)C12A—O3A1.376 (3)
C12—N11.326 (3)C13A—C15A1.352 (4)
C12—O31.385 (3)C13A—S1A1.718 (3)
C13—C141.364 (4)C14A—N2A1.305 (4)
C13—S11.713 (3)C14A—S1A1.699 (3)
C14—N21.387 (4)C14A—H14A0.9300
C14—C191.494 (5)C15A—N2A1.382 (4)
C15—N21.294 (4)C15A—C19A1.492 (4)
C15—S11.715 (3)C16A—O4A1.225 (3)
C15—H150.9300C16A—O5A1.349 (4)
C16—O41.209 (3)C17A—O5A1.446 (4)
C16—O51.344 (4)C17A—C18A1.461 (5)
C17—C181.406 (5)C17A—H17C0.9700
C17—O51.463 (4)C17A—H17D0.9700
C17—H17A0.9700C18A—H18D0.9600
C17—H17B0.9700C18A—H18E0.9600
C18—H18A0.9600C18A—H18F0.9600
C18—H18B0.9600C19A—H20X0.9600
C18—H18C0.9600C19A—H19X0.9600
C19—H19A0.9600C19A—H21X0.9600
C19—H19B0.9600N1—H1B0.8600
C19—H19C0.9600N1—H1C0.8600
C1A—C2A1.371 (4)N1A—H1A10.8600
C1A—C6A1.401 (4)N1A—H1A20.8600
C2—C1—C6121.0 (3)C2A—C3A—H3A119.5
C2—C1—H1119.5C3A—C4A—C5A118.8 (3)
C6—C1—H1119.5C3A—C4A—H4A120.6
C1—C2—C3119.7 (3)C5A—C4A—H4A120.6
C1—C2—H2120.2O1A—C5A—C4A117.2 (3)
C3—C2—H2120.2O1A—C5A—C6A121.1 (3)
C4—C3—C2120.6 (3)C4A—C5A—C6A121.7 (3)
C4—C3—H3119.7C5A—C6A—C1A118.3 (3)
C2—C3—H3119.7C5A—C6A—C9A116.8 (3)
C3—C4—C5118.9 (3)C1A—C6A—C9A124.9 (3)
C3—C4—H4120.5O2A—C7A—O1A116.9 (3)
C5—C4—H4120.5O2A—C7A—C8A125.5 (3)
C4—C5—O1116.8 (3)O1A—C7A—C8A117.6 (3)
C4—C5—C6121.8 (3)C9A—C8A—C7A119.1 (3)
O1—C5—C6121.4 (3)C9A—C8A—C10A122.8 (3)
C5—C6—C1117.9 (3)C7A—C8A—C10A118.1 (3)
C5—C6—C9116.4 (3)C8A—C9A—O3A122.6 (3)
C1—C6—C9125.7 (3)C8A—C9A—C6A123.2 (3)
O2—C7—O1116.7 (3)O3A—C9A—C6A114.2 (3)
O2—C7—C8125.3 (3)C8A—C10A—C11A109.1 (2)
O1—C7—C8118.0 (3)C8A—C10A—C13A109.8 (2)
C9—C8—C7119.3 (3)C11A—C10A—C13A113.2 (2)
C9—C8—C10122.2 (2)C8A—C10A—H10A108.2
C7—C8—C10118.4 (3)C11A—C10A—H10A108.2
C8—C9—O3122.8 (2)C13A—C10A—H10A108.2
C8—C9—C6123.2 (2)C12A—C11A—C16A117.8 (3)
O3—C9—C6114.0 (2)C12A—C11A—C10A121.6 (3)
C8—C10—C11109.1 (2)C16A—C11A—C10A120.5 (3)
C8—C10—C13111.1 (2)N1A—C12A—C11A128.5 (3)
C11—C10—C13113.8 (2)N1A—C12A—O3A109.0 (3)
C8—C10—H10107.5C11A—C12A—O3A122.4 (2)
C11—C10—H10107.5C15A—C13A—C10A129.3 (3)
C13—C10—H10107.5C15A—C13A—S1A110.1 (2)
C12—C11—C16117.6 (3)C10A—C13A—S1A120.6 (2)
C12—C11—C10121.6 (2)N2A—C14A—S1A115.3 (3)
C16—C11—C10120.7 (3)N2A—C14A—H14A122.3
N1—C12—C11129.2 (3)S1A—C14A—H14A122.3
N1—C12—O3108.9 (3)C13A—C15A—N2A114.7 (3)
C11—C12—O3121.9 (2)C13A—C15A—C19A127.1 (3)
C14—C13—C10128.9 (3)N2A—C15A—C19A118.2 (3)
C14—C13—S1109.6 (2)O4A—C16A—O5A120.5 (3)
C10—C13—S1121.5 (2)O4A—C16A—C11A126.8 (3)
C13—C14—N2115.1 (3)O5A—C16A—C11A112.7 (3)
C13—C14—C19126.7 (3)O5A—C17A—C18A109.2 (3)
N2—C14—C19118.2 (3)O5A—C17A—H17C109.8
N2—C15—S1115.2 (3)C18A—C17A—H17C109.8
N2—C15—H15122.4O5A—C17A—H17D109.8
S1—C15—H15122.4C18A—C17A—H17D109.8
O4—C16—O5121.7 (3)H17C—C17A—H17D108.3
O4—C16—C11126.7 (3)C17A—C18A—H18D109.5
O5—C16—C11111.5 (3)C17A—C18A—H18E109.5
C18—C17—O5110.4 (3)H18D—C18A—H18E109.5
C18—C17—H17A109.6C17A—C18A—H18F109.5
O5—C17—H17A109.6H18D—C18A—H18F109.5
C18—C17—H17B109.6H18E—C18A—H18F109.5
O5—C17—H17B109.6C15A—C19A—H20X109.5
H17A—C17—H17B108.1C15A—C19A—H19X109.5
C17—C18—H18A109.5H20X—C19A—H19X109.5
C17—C18—H18B109.5C15A—C19A—H21X109.5
H18A—C18—H18B109.5H20X—C19A—H21X109.5
C17—C18—H18C109.5H19X—C19A—H21X109.5
H18A—C18—H18C109.5C12—N1—H1B120.0
H18B—C18—H18C109.5C12—N1—H1C120.0
C14—C19—H19A109.5H1B—N1—H1C120.0
C14—C19—H19B109.5C15—N2—C14110.4 (3)
H19A—C19—H19B109.5C12A—N1A—H1A1120.0
C14—C19—H19C109.5C12A—N1A—H1A2120.0
H19A—C19—H19C109.5H1A1—N1A—H1A2120.0
H19B—C19—H19C109.5C14A—N2A—C15A110.4 (3)
C2A—C1A—C6A120.0 (3)C5—O1—C7121.6 (2)
C2A—C1A—H1A120.0C9—O3—C12117.7 (2)
C6A—C1A—H1A120.0C16—O5—C17115.7 (3)
C1A—C2A—C3A120.2 (3)C5A—O1A—C7A122.1 (2)
C1A—C2A—H2A119.9C9A—O3A—C12A118.4 (2)
C3A—C2A—H2A119.9C16A—O5A—C17A116.2 (3)
C4A—C3A—C2A121.0 (3)C13—S1—C1589.65 (17)
C4A—C3A—H3A119.5C14A—S1A—C13A89.39 (16)
C6—C1—C2—C31.0 (5)C7A—C8A—C9A—C6A3.1 (5)
C1—C2—C3—C40.8 (5)C10A—C8A—C9A—C6A176.5 (3)
C2—C3—C4—C50.0 (5)C5A—C6A—C9A—C8A1.0 (5)
C3—C4—C5—O1179.5 (3)C1A—C6A—C9A—C8A178.7 (3)
C3—C4—C5—C60.7 (5)C5A—C6A—C9A—O3A179.5 (3)
C4—C5—C6—C10.5 (4)C1A—C6A—C9A—O3A0.8 (4)
O1—C5—C6—C1179.3 (2)C9A—C8A—C10A—C11A15.1 (4)
C4—C5—C6—C9178.0 (3)C7A—C8A—C10A—C11A165.2 (3)
O1—C5—C6—C90.8 (4)C9A—C8A—C10A—C13A109.5 (3)
C2—C1—C6—C50.3 (5)C7A—C8A—C10A—C13A70.2 (3)
C2—C1—C6—C9178.7 (3)C8A—C10A—C11A—C12A14.3 (4)
O2—C7—C8—C9178.7 (3)C13A—C10A—C11A—C12A108.3 (3)
O1—C7—C8—C92.0 (4)C8A—C10A—C11A—C16A165.9 (3)
O2—C7—C8—C100.9 (5)C13A—C10A—C11A—C16A71.4 (4)
O1—C7—C8—C10179.8 (2)C16A—C11A—C12A—N1A1.9 (5)
C7—C8—C9—O3176.8 (2)C10A—C11A—C12A—N1A177.8 (3)
C10—C8—C9—O30.9 (4)C16A—C11A—C12A—O3A178.7 (3)
C7—C8—C9—C62.9 (4)C10A—C11A—C12A—O3A1.6 (5)
C10—C8—C9—C6179.4 (3)C8A—C10A—C13A—C15A109.8 (3)
C5—C6—C9—C82.3 (4)C11A—C10A—C13A—C15A128.0 (3)
C1—C6—C9—C8179.4 (3)C8A—C10A—C13A—S1A69.4 (3)
C5—C6—C9—O3177.5 (2)C11A—C10A—C13A—S1A52.8 (3)
C1—C6—C9—O30.9 (4)C10A—C13A—C15A—N2A179.1 (3)
C9—C8—C10—C1117.5 (4)S1A—C13A—C15A—N2A0.2 (3)
C7—C8—C10—C11160.3 (3)C10A—C13A—C15A—C19A0.6 (5)
C9—C8—C10—C13108.7 (3)S1A—C13A—C15A—C19A179.9 (3)
C7—C8—C10—C1373.5 (3)C12A—C11A—C16A—O4A2.4 (5)
C8—C10—C11—C1218.3 (4)C10A—C11A—C16A—O4A177.4 (3)
C13—C10—C11—C12106.3 (3)C12A—C11A—C16A—O5A177.0 (3)
C8—C10—C11—C16158.2 (3)C10A—C11A—C16A—O5A3.3 (4)
C13—C10—C11—C1677.2 (3)S1—C15—N2—C141.1 (3)
C16—C11—C12—N15.1 (5)C13—C14—N2—C151.7 (4)
C10—C11—C12—N1178.3 (3)C19—C14—N2—C15177.3 (3)
C16—C11—C12—O3173.7 (3)S1A—C14A—N2A—C15A0.9 (3)
C10—C11—C12—O32.9 (4)C13A—C15A—N2A—C14A0.4 (4)
C8—C10—C13—C14116.2 (3)C19A—C15A—N2A—C14A179.2 (3)
C11—C10—C13—C14120.3 (3)C4—C5—O1—C7178.8 (3)
C8—C10—C13—S165.5 (3)C6—C5—O1—C70.1 (4)
C11—C10—C13—S158.1 (3)O2—C7—O1—C5180.0 (3)
C10—C13—C14—N2176.9 (3)C8—C7—O1—C50.6 (4)
S1—C13—C14—N21.6 (3)C8—C9—O3—C1216.9 (4)
C10—C13—C14—C194.1 (5)C6—C9—O3—C12162.8 (2)
S1—C13—C14—C19177.4 (3)N1—C12—O3—C9163.3 (2)
C12—C11—C16—O42.6 (5)C11—C12—O3—C915.8 (4)
C10—C11—C16—O4179.2 (3)O4—C16—O5—C171.7 (5)
C12—C11—C16—O5178.1 (3)C11—C16—O5—C17177.7 (3)
C10—C11—C16—O51.5 (4)C18—C17—O5—C16163.9 (4)
C6A—C1A—C2A—C3A0.0 (5)C4A—C5A—O1A—C7A179.7 (3)
C1A—C2A—C3A—C4A0.2 (5)C6A—C5A—O1A—C7A0.2 (4)
C2A—C3A—C4A—C5A0.5 (5)O2A—C7A—O1A—C5A178.2 (3)
C3A—C4A—C5A—O1A179.5 (3)C8A—C7A—O1A—C5A2.3 (4)
C3A—C4A—C5A—C6A0.5 (5)C8A—C9A—O3A—C12A12.0 (4)
O1A—C5A—C6A—C1A179.7 (3)C6A—C9A—O3A—C12A168.6 (2)
C4A—C5A—C6A—C1A0.2 (5)N1A—C12A—O3A—C9A167.9 (3)
O1A—C5A—C6A—C9A0.5 (4)C11A—C12A—O3A—C9A12.6 (4)
C4A—C5A—C6A—C9A179.6 (3)O4A—C16A—O5A—C17A1.5 (5)
C2A—C1A—C6A—C5A0.1 (5)C11A—C16A—O5A—C17A179.1 (3)
C2A—C1A—C6A—C9A179.8 (3)C18A—C17A—O5A—C16A176.8 (4)
O2A—C7A—C8A—C9A176.8 (3)C14—C13—S1—C150.8 (2)
O1A—C7A—C8A—C9A3.7 (4)C10—C13—S1—C15177.8 (2)
O2A—C7A—C8A—C10A3.5 (5)N2—C15—S1—C130.2 (3)
O1A—C7A—C8A—C10A176.0 (2)N2A—C14A—S1A—C13A0.9 (2)
C7A—C8A—C9A—O3A177.4 (3)C15A—C13A—S1A—C14A0.6 (2)
C10A—C8A—C9A—O3A2.9 (5)C10A—C13A—S1A—C14A178.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O40.862.112.698 (3)125
N1—H1B···N2Ai0.862.493.152 (3)135
N1—H1C···N2ii0.862.273.116 (4)167
N1A—H1A2···N2Aiii0.862.132.988 (4)174
N1A—H1A1···O4A0.862.092.690 (3)126
N1A—H1A1···O4ii0.862.522.936 (3)111
Symmetry codes: (i) x, y, z+1; (ii) x+1/2, y+1/2, z+3/2; (iii) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O40.862.112.698 (3)125.3
N1—H1B···N2Ai0.862.493.152 (3)135.0
N1—H1C···N2ii0.862.273.116 (4)167.1
N1A—H1A2···N2Aiii0.862.132.988 (4)173.5
N1A—H1A1···O4A0.862.092.690 (3)126.4
N1A—H1A1···O4ii0.862.522.936 (3)110.6
Symmetry codes: (i) x, y, z+1; (ii) x+1/2, y+1/2, z+3/2; (iii) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection and Orchid Chemicals and Pharmaceuticals, Chennai, India for providing necessary laboratory facilities.

References

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Volume 69| Part 9| September 2013| Pages o1411-o1412
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