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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodi­thio­ate

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, and bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com

(Received 14 July 2013; accepted 27 July 2013; online 3 August 2013)

There are two independent mol­ecules in the asymmetric unit of the title compound, C16H15NO3S2, in which the pyrrolidine rings adopt envelope conformations, with a methyl­ene C atom as the flap. The dihedral angles betweeen the near-planar 2H-chromene ring systems [maximum deviations = 0.0167 (20) and 0.0136 (19) Å] and the pyrrolidine rings (all atoms) are 83.83 (11) and 82.43 (11)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur for one of the mol­ecules. Further C—H⋯O links involving both mol­ecules generate a three-dimensional network.

Related literature

For a related structure and the synthesis of the title compound, see: Mahabaleshwaraiah et al. (2012[Mahabaleshwaraiah, N. M., Kumar, K. M., Kotresh, O., Al-eryani, W. F. A. & Devarajegowda, H. C. (2012). Acta Cryst. E68, o1566.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15NO3S2

  • Mr = 333.41

  • Triclinic, [P \overline 1]

  • a = 9.7158 (2) Å

  • b = 12.5040 (2) Å

  • c = 13.5925 (2) Å

  • α = 106.415 (1)°

  • β = 100.882 (1)°

  • γ = 94.854 (1)°

  • V = 1538.74 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 296 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

  • 21575 measured reflections

  • 5420 independent reflections

  • 4477 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.109

  • S = 1.09

  • 5420 reflections

  • 397 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9A—H9A⋯O5Bi 0.93 2.48 3.307 (2) 149
C15A—H15A⋯O5Bi 0.93 2.50 3.319 (3) 147
C9B—H9B⋯O5Ai 0.93 2.46 3.288 (3) 149
C15B—H15B⋯O5Ai 0.93 2.50 3.319 (3) 146
C17B—H17B⋯O3Bii 0.97 2.47 3.432 (3) 170
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+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


Comment top

As part of our ongoing structural studies of coumarin derivatives with possible biological activity (Mahabaleshwaraiah et al., 2012), we now describe the structure of the title compound, (I).

There are two independent molecules in the asymmetric unit of 2-oxo-2- (2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodithioate is shown in Fig. 1. The 2H-chromene ring systems (O3a/C7a–C15a) and (O3b/C7b–C15b) are nearly planar, with a maximum deviation of 0.0167 (20) Å and 0.0136 (19) Å respectively. The pyrrolidine rings (N6a/C19a—C22a) and (N6b/C19b—C22b) are not coplanar with the 2H-chromene ring systems (O3a/C7a–C15a) and (O3b/C7b–C15b); the dihedral angles between two planes being 83.83 (11)° and 82.43 (11)° in the two molecules. In the crystal, inversion related C17B—H17B···O3B hydrogen bonds generate R22(12) loops.

Related literature top

For a related structure and the synthesis of the title compound, see: Mahabaleshwaraiah et al. (2012).

Experimental top

This compound was prepared according to the reported method (Mahabaleshwaraiah et al., 2012). Colourless needles were grown from a mixed solution of EtOH/CHCl3 (v/v = 2/1) by slow evaporation at room temperature. Yield = 88%, m.p. 441 K.

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, C—H = 0.97 Å for methylene 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.
2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodithioate top
Crystal data top
C16H15NO3S2Z = 4
Mr = 333.41F(000) = 696
Triclinic, P1Dx = 1.439 Mg m3
Hall symbol: -P 1Melting point: 441 K
a = 9.7158 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5040 (2) ÅCell parameters from 5420 reflections
c = 13.5925 (2) Åθ = 1.7–25.0°
α = 106.415 (1)°µ = 0.36 mm1
β = 100.882 (1)°T = 296 K
γ = 94.854 (1)°Plate, colourless
V = 1538.74 (5) Å30.24 × 0.20 × 0.12 mm
Data collection top
Bruker SMART CCD
diffractometer
5420 independent reflections
Radiation source: fine-focus sealed tube4477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω and ϕ scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1111
Tmin = 0.770, Tmax = 1.000k = 1414
21575 measured reflectionsl = 1616
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.3725P]
where P = (Fo2 + 2Fc2)/3
5420 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C16H15NO3S2γ = 94.854 (1)°
Mr = 333.41V = 1538.74 (5) Å3
Triclinic, P1Z = 4
a = 9.7158 (2) ÅMo Kα radiation
b = 12.5040 (2) ŵ = 0.36 mm1
c = 13.5925 (2) ÅT = 296 K
α = 106.415 (1)°0.24 × 0.20 × 0.12 mm
β = 100.882 (1)°
Data collection top
Bruker SMART CCD
diffractometer
5420 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4477 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 1.000Rint = 0.023
21575 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.09Δρmax = 0.34 e Å3
5420 reflectionsΔρmin = 0.38 e Å3
397 parameters
Special details top

Experimental. IR (KBr): 636 cm-1(C—S), 1254 cm-1(C=S), 1070 cm-1(C—O), 854 cm-1 (C—N),1125 cm-1(C—O—C), 1694 cm-1 (C=O), 1731 cm-1(Coumarin C=O). GCMS: m/e: 335. 1H NMR (400 MHz, CDCl3, δ,. p.p.m): 2.11(m, 2H, Pyrrolidine-CH2) 2.16(m, 2H, Pyrrolidine-CH2), 3.68(t, 2H, Pyrrolidine-CH2), 3.91(t, 2H, Pyrrolidine-CH2),4.59(s, 2H, Methylene-CH2), 7.24(t, 1H, Ar—H), 7.41(d, 1H, Ar—H), 7.49(t, 1H, Ar—H), 7.65(d,1H, Ar—H),8.16(s, 1H, Ar—H). Elemental analysis for C16H15NO3S2: C, 57.58; H, 4.46; N, 4.13.

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
S1B0.46924 (6)0.77672 (4)0.81900 (5)0.05885 (16)
S2B0.72066 (6)0.92077 (6)0.98610 (5)0.07162 (19)
O3B0.74479 (16)0.48705 (12)1.07902 (11)0.0598 (4)
O4B0.6049 (2)0.61413 (15)1.07471 (13)0.0813 (5)
O5B0.68855 (18)0.62686 (13)0.78589 (12)0.0704 (4)
N6B0.55263 (15)0.98720 (12)0.84624 (12)0.0455 (4)
C7B0.6776 (2)0.55533 (17)1.02806 (16)0.0566 (5)
C8B0.7036 (2)0.54840 (15)0.92381 (15)0.0470 (4)
C9B0.7859 (2)0.47448 (15)0.88210 (15)0.0474 (4)
H9B0.80080.47020.81560.057*
C10B0.85098 (19)0.40263 (15)0.93565 (15)0.0461 (4)
C11B0.8291 (2)0.41211 (16)1.03604 (15)0.0502 (5)
C12B0.8900 (2)0.34839 (19)1.09553 (18)0.0627 (6)
H12B0.87390.35591.16230.075*
C13B0.9745 (2)0.27392 (19)1.05399 (19)0.0652 (6)
H13B1.01650.23041.09310.078*
C14B0.9988 (2)0.26217 (17)0.95419 (18)0.0612 (5)
H14B1.05650.21100.92720.073*
C15B0.9378 (2)0.32573 (16)0.89536 (16)0.0549 (5)
H15B0.95430.31760.82860.066*
C16B0.6446 (2)0.62295 (15)0.86268 (16)0.0513 (5)
C17B0.5292 (3)0.68791 (18)0.89563 (19)0.0650 (6)
H17A0.56300.73420.96830.078*
H17B0.44890.63470.89280.078*
C18B0.58542 (19)0.90472 (16)0.88551 (15)0.0464 (4)
C19B0.4308 (2)0.97956 (16)0.76104 (17)0.0568 (5)
H19A0.34460.94540.77300.068*
H19B0.44580.93590.69360.068*
C20B0.4238 (3)1.10145 (19)0.7655 (2)0.0776 (7)
H20A0.39211.10740.69540.093*
H20B0.35881.13280.80820.093*
C21B0.5699 (3)1.16160 (18)0.8132 (2)0.0697 (6)
H21A0.56871.24020.84960.084*
H21B0.62451.15740.75970.084*
C22B0.6319 (2)1.10183 (16)0.88939 (17)0.0573 (5)
H22A0.73231.10070.89260.069*
H22B0.61851.13810.95940.069*
S1A0.04479 (6)0.82131 (5)0.38879 (5)0.06212 (17)
S2A0.26976 (7)0.90519 (6)0.46861 (6)0.0836 (2)
O3A0.24069 (18)0.53930 (13)0.65250 (11)0.0711 (4)
O4A0.1038 (2)0.66877 (16)0.64994 (13)0.0907 (6)
O5A0.0825 (2)0.61136 (15)0.32787 (13)0.0935 (6)
N6A0.09101 (16)0.98182 (13)0.34318 (13)0.0503 (4)
C7A0.1645 (3)0.60259 (19)0.59960 (17)0.0620 (5)
C8A0.1661 (2)0.57919 (16)0.48808 (15)0.0512 (5)
C9A0.2381 (2)0.49904 (15)0.44312 (15)0.0518 (5)
H9A0.23580.48360.37170.062*
C10A0.3180 (2)0.43666 (15)0.50018 (16)0.0507 (5)
C11A0.3162 (2)0.45940 (17)0.60620 (16)0.0585 (5)
C12A0.3893 (3)0.4023 (2)0.6678 (2)0.0774 (7)
H12A0.38540.41670.73810.093*
C13A0.4674 (3)0.3242 (2)0.6226 (2)0.0787 (7)
H13A0.51830.28610.66340.094*
C14A0.4726 (3)0.30032 (18)0.5179 (2)0.0698 (6)
H14A0.52680.24700.48910.084*
C15A0.3977 (2)0.35547 (16)0.45664 (18)0.0598 (5)
H15A0.40010.33870.38590.072*
C16A0.0888 (2)0.64165 (17)0.42166 (16)0.0582 (5)
C17A0.0179 (3)0.73924 (18)0.47142 (18)0.0632 (6)
H17C0.08470.78850.53330.076*
H17D0.06160.71010.49480.076*
C18A0.1125 (2)0.91016 (16)0.39811 (16)0.0524 (5)
C19A0.0455 (2)0.99070 (17)0.28054 (16)0.0546 (5)
H19C0.10661.02530.32530.065*
H19D0.09350.91720.23510.065*
C20A0.0040 (3)1.0652 (2)0.2166 (2)0.0765 (7)
H20C0.01061.01970.14970.092*
H20D0.07731.11070.20350.092*
C21A0.1297 (2)1.1377 (2)0.2816 (2)0.0690 (6)
H21C0.10991.20570.32910.083*
H21D0.18771.15870.23730.083*
C22A0.2031 (2)1.06729 (19)0.3421 (2)0.0672 (6)
H22C0.27401.03220.30780.081*
H22D0.24891.11310.41320.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1B0.0681 (3)0.0498 (3)0.0632 (4)0.0148 (2)0.0129 (3)0.0236 (2)
S2B0.0666 (4)0.0952 (4)0.0564 (4)0.0269 (3)0.0002 (3)0.0330 (3)
O3B0.0772 (9)0.0722 (9)0.0451 (8)0.0197 (7)0.0246 (7)0.0319 (7)
O4B0.1223 (14)0.0904 (11)0.0576 (10)0.0506 (11)0.0490 (10)0.0349 (9)
O5B0.1029 (12)0.0805 (10)0.0563 (9)0.0452 (9)0.0402 (9)0.0419 (8)
N6B0.0439 (8)0.0489 (8)0.0451 (9)0.0114 (6)0.0063 (7)0.0177 (7)
C7B0.0768 (14)0.0566 (11)0.0469 (12)0.0160 (10)0.0236 (10)0.0238 (10)
C8B0.0619 (11)0.0454 (10)0.0391 (10)0.0085 (8)0.0164 (9)0.0181 (8)
C9B0.0622 (11)0.0472 (10)0.0358 (10)0.0058 (8)0.0132 (8)0.0168 (8)
C10B0.0550 (10)0.0449 (9)0.0404 (10)0.0045 (8)0.0087 (8)0.0180 (8)
C11B0.0556 (11)0.0541 (11)0.0460 (11)0.0041 (9)0.0133 (9)0.0233 (9)
C12B0.0713 (13)0.0773 (14)0.0518 (13)0.0088 (11)0.0137 (10)0.0398 (11)
C13B0.0685 (13)0.0698 (14)0.0658 (15)0.0113 (11)0.0043 (11)0.0407 (12)
C14B0.0667 (13)0.0572 (12)0.0635 (14)0.0165 (10)0.0085 (11)0.0260 (11)
C15B0.0667 (12)0.0539 (11)0.0458 (12)0.0113 (9)0.0098 (9)0.0191 (9)
C16B0.0695 (12)0.0454 (10)0.0445 (11)0.0122 (9)0.0195 (10)0.0168 (9)
C17B0.0857 (15)0.0598 (12)0.0717 (15)0.0276 (11)0.0369 (12)0.0374 (11)
C18B0.0490 (10)0.0569 (11)0.0417 (10)0.0206 (8)0.0177 (8)0.0195 (9)
C19B0.0535 (11)0.0582 (11)0.0579 (13)0.0092 (9)0.0022 (9)0.0259 (10)
C20B0.0760 (15)0.0692 (14)0.0923 (19)0.0148 (12)0.0030 (13)0.0449 (14)
C21B0.0829 (16)0.0533 (12)0.0761 (16)0.0101 (11)0.0146 (13)0.0267 (11)
C22B0.0589 (12)0.0525 (11)0.0567 (13)0.0043 (9)0.0088 (10)0.0146 (10)
S1A0.0642 (3)0.0604 (3)0.0718 (4)0.0186 (2)0.0199 (3)0.0301 (3)
S2A0.0641 (4)0.1074 (5)0.0888 (5)0.0289 (3)0.0023 (3)0.0495 (4)
O3A0.1042 (12)0.0781 (10)0.0399 (8)0.0224 (9)0.0178 (8)0.0279 (8)
O4A0.1331 (16)0.1087 (14)0.0493 (10)0.0566 (12)0.0395 (10)0.0302 (10)
O5A0.1646 (18)0.0908 (12)0.0433 (10)0.0714 (12)0.0306 (10)0.0290 (9)
N6A0.0475 (8)0.0547 (9)0.0514 (10)0.0140 (7)0.0102 (7)0.0191 (8)
C7A0.0842 (15)0.0650 (13)0.0432 (12)0.0146 (11)0.0165 (11)0.0240 (10)
C8A0.0678 (12)0.0491 (10)0.0382 (11)0.0061 (9)0.0128 (9)0.0161 (9)
C9A0.0715 (13)0.0500 (10)0.0363 (10)0.0061 (9)0.0115 (9)0.0183 (9)
C10A0.0598 (11)0.0456 (10)0.0464 (11)0.0001 (8)0.0059 (9)0.0195 (9)
C11A0.0740 (13)0.0546 (11)0.0458 (12)0.0018 (10)0.0046 (10)0.0216 (10)
C12A0.1071 (19)0.0735 (15)0.0520 (14)0.0074 (14)0.0004 (13)0.0332 (12)
C13A0.0972 (18)0.0650 (14)0.0736 (18)0.0093 (13)0.0082 (14)0.0393 (13)
C14A0.0748 (14)0.0555 (12)0.0796 (18)0.0122 (10)0.0044 (12)0.0292 (12)
C15A0.0723 (13)0.0510 (11)0.0575 (13)0.0070 (10)0.0085 (11)0.0233 (10)
C16A0.0842 (15)0.0558 (11)0.0418 (12)0.0196 (10)0.0203 (10)0.0192 (9)
C17A0.0853 (15)0.0601 (12)0.0555 (13)0.0197 (11)0.0271 (11)0.0256 (11)
C18A0.0589 (11)0.0550 (11)0.0463 (11)0.0226 (9)0.0147 (9)0.0142 (9)
C19A0.0530 (11)0.0556 (11)0.0536 (12)0.0135 (9)0.0046 (9)0.0175 (10)
C20A0.0835 (16)0.0745 (15)0.0727 (17)0.0067 (12)0.0010 (13)0.0364 (13)
C21A0.0718 (14)0.0744 (14)0.0741 (16)0.0134 (11)0.0256 (12)0.0365 (13)
C22A0.0547 (12)0.0714 (14)0.0800 (17)0.0060 (10)0.0163 (11)0.0301 (12)
Geometric parameters (Å, º) top
S1B—C18B1.773 (2)S1A—C18A1.774 (2)
S1B—C17B1.787 (2)S1A—C17A1.785 (2)
S2B—C18B1.6608 (19)S2A—C18A1.659 (2)
O3B—C11B1.375 (2)O3A—C11A1.370 (3)
O3B—C7B1.376 (2)O3A—C7A1.382 (2)
O4B—C7B1.198 (2)O4A—C7A1.190 (3)
O5B—C16B1.211 (2)O5A—C16A1.211 (2)
N6B—C18B1.324 (2)N6A—C18A1.325 (2)
N6B—C19B1.467 (2)N6A—C22A1.465 (3)
N6B—C22B1.469 (2)N6A—C19A1.466 (2)
C7B—C8B1.466 (3)C7A—C8A1.464 (3)
C8B—C9B1.348 (3)C8A—C9A1.342 (3)
C8B—C16B1.495 (3)C8A—C16A1.494 (3)
C9B—C10B1.424 (2)C9A—C10A1.425 (3)
C9B—H9B0.9300C9A—H9A0.9300
C10B—C11B1.394 (3)C10A—C11A1.392 (3)
C10B—C15B1.396 (3)C10A—C15A1.395 (3)
C11B—C12B1.379 (3)C11A—C12A1.383 (3)
C12B—C13B1.367 (3)C12A—C13A1.368 (4)
C12B—H12B0.9300C12A—H12A0.9300
C13B—C14B1.390 (3)C13A—C14A1.381 (4)
C13B—H13B0.9300C13A—H13A0.9300
C14B—C15B1.372 (3)C14A—C15A1.371 (3)
C14B—H14B0.9300C14A—H14A0.9300
C15B—H15B0.9300C15A—H15A0.9300
C16B—C17B1.502 (3)C16A—C17A1.507 (3)
C17B—H17A0.9700C17A—H17C0.9700
C17B—H17B0.9700C17A—H17D0.9700
C19B—C20B1.516 (3)C19A—C20A1.520 (3)
C19B—H19A0.9700C19A—H19C0.9700
C19B—H19B0.9700C19A—H19D0.9700
C20B—C21B1.483 (3)C20A—C21A1.485 (3)
C20B—H20A0.9700C20A—H20C0.9700
C20B—H20B0.9700C20A—H20D0.9700
C21B—C22B1.507 (3)C21A—C22A1.501 (3)
C21B—H21A0.9700C21A—H21C0.9700
C21B—H21B0.9700C21A—H21D0.9700
C22B—H22A0.9700C22A—H22C0.9700
C22B—H22B0.9700C22A—H22D0.9700
C18B—S1B—C17B102.01 (11)C18A—S1A—C17A101.77 (10)
C11B—O3B—C7B123.64 (15)C11A—O3A—C7A123.44 (16)
C18B—N6B—C19B125.64 (16)C18A—N6A—C22A123.09 (17)
C18B—N6B—C22B122.64 (16)C18A—N6A—C19A125.71 (17)
C19B—N6B—C22B111.60 (14)C22A—N6A—C19A111.15 (16)
O4B—C7B—O3B115.83 (18)O4A—C7A—O3A116.01 (19)
O4B—C7B—C8B127.55 (19)O4A—C7A—C8A127.7 (2)
O3B—C7B—C8B116.62 (17)O3A—C7A—C8A116.33 (19)
C9B—C8B—C7B119.33 (17)C9A—C8A—C7A119.63 (18)
C9B—C8B—C16B118.46 (16)C9A—C8A—C16A118.44 (17)
C7B—C8B—C16B122.20 (17)C7A—C8A—C16A121.92 (18)
C8B—C9B—C10B122.74 (17)C8A—C9A—C10A122.76 (18)
C8B—C9B—H9B118.6C8A—C9A—H9A118.6
C10B—C9B—H9B118.6C10A—C9A—H9A118.6
C11B—C10B—C15B118.09 (17)C11A—C10A—C15A118.51 (19)
C11B—C10B—C9B117.53 (17)C11A—C10A—C9A117.30 (19)
C15B—C10B—C9B124.36 (17)C15A—C10A—C9A124.19 (19)
O3B—C11B—C12B117.76 (18)O3A—C11A—C12A118.0 (2)
O3B—C11B—C10B120.10 (16)O3A—C11A—C10A120.50 (18)
C12B—C11B—C10B122.14 (19)C12A—C11A—C10A121.5 (2)
C13B—C12B—C11B118.4 (2)C13A—C12A—C11A118.2 (2)
C13B—C12B—H12B120.8C13A—C12A—H12A120.9
C11B—C12B—H12B120.8C11A—C12A—H12A120.9
C12B—C13B—C14B121.07 (19)C12A—C13A—C14A121.7 (2)
C12B—C13B—H13B119.5C12A—C13A—H13A119.1
C14B—C13B—H13B119.5C14A—C13A—H13A119.1
C15B—C14B—C13B120.3 (2)C15A—C14A—C13A119.8 (2)
C15B—C14B—H14B119.9C15A—C14A—H14A120.1
C13B—C14B—H14B119.9C13A—C14A—H14A120.1
C14B—C15B—C10B120.04 (19)C14A—C15A—C10A120.2 (2)
C14B—C15B—H15B120.0C14A—C15A—H15A119.9
C10B—C15B—H15B120.0C10A—C15A—H15A119.9
O5B—C16B—C8B118.99 (17)O5A—C16A—C8A118.90 (18)
O5B—C16B—C17B121.65 (18)O5A—C16A—C17A121.16 (19)
C8B—C16B—C17B119.33 (17)C8A—C16A—C17A119.93 (17)
C16B—C17B—S1B115.66 (15)C16A—C17A—S1A115.49 (15)
C16B—C17B—H17A108.4C16A—C17A—H17C108.4
S1B—C17B—H17A108.4S1A—C17A—H17C108.4
C16B—C17B—H17B108.4C16A—C17A—H17D108.4
S1B—C17B—H17B108.4S1A—C17A—H17D108.4
H17A—C17B—H17B107.4H17C—C17A—H17D107.5
N6B—C18B—S2B123.21 (15)N6A—C18A—S2A123.39 (16)
N6B—C18B—S1B112.52 (14)N6A—C18A—S1A112.74 (14)
S2B—C18B—S1B124.27 (11)S2A—C18A—S1A123.87 (12)
N6B—C19B—C20B103.42 (16)N6A—C19A—C20A103.19 (17)
N6B—C19B—H19A111.1N6A—C19A—H19C111.1
C20B—C19B—H19A111.1C20A—C19A—H19C111.1
N6B—C19B—H19B111.1N6A—C19A—H19D111.1
C20B—C19B—H19B111.1C20A—C19A—H19D111.1
H19A—C19B—H19B109.0H19C—C19A—H19D109.1
C21B—C20B—C19B105.75 (17)C21A—C20A—C19A105.50 (19)
C21B—C20B—H20A110.6C21A—C20A—H20C110.6
C19B—C20B—H20A110.6C19A—C20A—H20C110.6
C21B—C20B—H20B110.6C21A—C20A—H20D110.6
C19B—C20B—H20B110.6C19A—C20A—H20D110.6
H20A—C20B—H20B108.7H20C—C20A—H20D108.8
C20B—C21B—C22B105.07 (18)C20A—C21A—C22A105.23 (18)
C20B—C21B—H21A110.7C20A—C21A—H21C110.7
C22B—C21B—H21A110.7C22A—C21A—H21C110.7
C20B—C21B—H21B110.7C20A—C21A—H21D110.7
C22B—C21B—H21B110.7C22A—C21A—H21D110.7
H21A—C21B—H21B108.8H21C—C21A—H21D108.8
N6B—C22B—C21B104.04 (16)N6A—C22A—C21A105.22 (17)
N6B—C22B—H22A110.9N6A—C22A—H22C110.7
C21B—C22B—H22A110.9C21A—C22A—H22C110.7
N6B—C22B—H22B110.9N6A—C22A—H22D110.7
C21B—C22B—H22B110.9C21A—C22A—H22D110.7
H22A—C22B—H22B109.0H22C—C22A—H22D108.8
C11B—O3B—C7B—O4B178.2 (2)C11A—O3A—C7A—O4A179.9 (2)
C11B—O3B—C7B—C8B2.1 (3)C11A—O3A—C7A—C8A0.8 (3)
O4B—C7B—C8B—C9B178.1 (2)O4A—C7A—C8A—C9A178.3 (2)
O3B—C7B—C8B—C9B2.3 (3)O3A—C7A—C8A—C9A0.6 (3)
O4B—C7B—C8B—C16B3.5 (4)O4A—C7A—C8A—C16A1.3 (4)
O3B—C7B—C8B—C16B176.11 (17)O3A—C7A—C8A—C16A179.78 (18)
C7B—C8B—C9B—C10B0.7 (3)C7A—C8A—C9A—C10A1.9 (3)
C16B—C8B—C9B—C10B177.76 (17)C16A—C8A—C9A—C10A178.45 (18)
C8B—C9B—C10B—C11B1.1 (3)C8A—C9A—C10A—C11A1.8 (3)
C8B—C9B—C10B—C15B179.45 (19)C8A—C9A—C10A—C15A177.80 (19)
C7B—O3B—C11B—C12B179.84 (18)C7A—O3A—C11A—C12A179.4 (2)
C7B—O3B—C11B—C10B0.3 (3)C7A—O3A—C11A—C10A0.9 (3)
C15B—C10B—C11B—O3B179.76 (17)C15A—C10A—C11A—O3A179.27 (18)
C9B—C10B—C11B—O3B1.3 (3)C9A—C10A—C11A—O3A0.4 (3)
C15B—C10B—C11B—C12B0.0 (3)C15A—C10A—C11A—C12A1.0 (3)
C9B—C10B—C11B—C12B178.46 (18)C9A—C10A—C11A—C12A179.3 (2)
O3B—C11B—C12B—C13B179.70 (19)O3A—C11A—C12A—C13A178.6 (2)
C10B—C11B—C12B—C13B0.1 (3)C10A—C11A—C12A—C13A1.7 (4)
C11B—C12B—C13B—C14B0.1 (3)C11A—C12A—C13A—C14A1.1 (4)
C12B—C13B—C14B—C15B0.1 (3)C12A—C13A—C14A—C15A0.2 (4)
C13B—C14B—C15B—C10B0.0 (3)C13A—C14A—C15A—C10A0.9 (3)
C11B—C10B—C15B—C14B0.0 (3)C11A—C10A—C15A—C14A0.3 (3)
C9B—C10B—C15B—C14B178.29 (18)C9A—C10A—C15A—C14A179.32 (19)
C9B—C8B—C16B—O5B10.7 (3)C9A—C8A—C16A—O5A6.7 (3)
C7B—C8B—C16B—O5B167.7 (2)C7A—C8A—C16A—O5A172.9 (2)
C9B—C8B—C16B—C17B167.16 (19)C9A—C8A—C16A—C17A174.44 (19)
C7B—C8B—C16B—C17B14.4 (3)C7A—C8A—C16A—C17A6.0 (3)
O5B—C16B—C17B—S1B3.5 (3)O5A—C16A—C17A—S1A11.3 (3)
C8B—C16B—C17B—S1B178.68 (15)C8A—C16A—C17A—S1A169.88 (16)
C18B—S1B—C17B—C16B89.01 (19)C18A—S1A—C17A—C16A80.90 (19)
C19B—N6B—C18B—S2B176.91 (15)C22A—N6A—C18A—S2A2.4 (3)
C22B—N6B—C18B—S2B1.1 (3)C19A—N6A—C18A—S2A179.34 (15)
C19B—N6B—C18B—S1B3.0 (2)C22A—N6A—C18A—S1A177.18 (16)
C22B—N6B—C18B—S1B178.87 (14)C19A—N6A—C18A—S1A0.2 (2)
C17B—S1B—C18B—N6B175.02 (14)C17A—S1A—C18A—N6A178.87 (15)
C17B—S1B—C18B—S2B4.90 (15)C17A—S1A—C18A—S2A0.69 (16)
C18B—N6B—C19B—C20B167.00 (19)C18A—N6A—C19A—C20A167.79 (19)
C22B—N6B—C19B—C20B9.2 (2)C22A—N6A—C19A—C20A15.0 (2)
N6B—C19B—C20B—C21B25.7 (3)N6A—C19A—C20A—C21A28.4 (2)
C19B—C20B—C21B—C22B32.7 (3)C19A—C20A—C21A—C22A31.4 (3)
C18B—N6B—C22B—C21B173.23 (18)C18A—N6A—C22A—C21A173.35 (19)
C19B—N6B—C22B—C21B10.4 (2)C19A—N6A—C22A—C21A4.0 (2)
C20B—C21B—C22B—N6B26.3 (2)C20A—C21A—C22A—N6A21.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9A—H9A···O5Bi0.932.483.307 (2)149
C15A—H15A···O5Bi0.932.503.319 (3)147
C9B—H9B···O5Ai0.932.463.288 (3)149
C15B—H15B···O5Ai0.932.503.319 (3)146
C17B—H17B···O3Bii0.972.473.432 (3)170
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9A—H9A···O5Bi0.932.483.307 (2)149
C15A—H15A···O5Bi0.932.503.319 (3)147
C9B—H9B···O5Ai0.932.463.288 (3)149
C15B—H15B···O5Ai0.932.503.319 (3)146
C17B—H17B···O3Bii0.972.473.432 (3)170
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2.
 

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, the X-ray data collection and the GCMS, IR, CHNS and NMR data. KMM is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

First citationBruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationMahabaleshwaraiah, N. M., Kumar, K. M., Kotresh, O., Al-eryani, W. F. A. & Devarajegowda, H. C. (2012). Acta Cryst. E68, o1566.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds