supplementary materials


hb7098 scheme

Acta Cryst. (2013). E69, o1208-o1209    [ doi:10.1107/S1600536813017704 ]

5''-(4-Nitrobenzylidene)-7'-(4-nitrophenyl)-1''-methyl-1',3',5',6',7',7a'-hexahydrodispiro[acenaphthylene-1,5'-pyrrolo[1,2-c][1,3]thiazole-6',3''-piperidine]-2,4''(1H)-dione including an unknown solvate

R. Vishnupriya, J. Suresh, S. Sivakumar, R. R. Kumar and P. L. N. Lakshman

Abstract top

The title compound, C35H28N4O6S, crystallizes with two molecules in the asymmetric unit. In both molecules, the piperidine ring adopts a shallow-chair conformation, the thiazole ring adopts a twisted conformation about the Cm-N bond (m = methine) and the pyrrole ring adopts an envelope conformation with the C atom shared with the thiazole ring as the flap. In the crystal, inversion dimers linked by pairs of C-H...O interactions generate R22(34) loops for one of the asymmetric molecules. Further C-H...O links also involving the other molecule lead to a three-dimesional network. The contribution of the highly disordered solvent to the scattering was removed with SQUEEZE option of PLATON [Spek (2009). Acta Cryst. D65, 148-155]. The solvent contribution is not included in the reported molecular weight and density.

Comment top

As part of our ongoing studies of spiro-pyrrolidine compounds (Suresh et al., 2013), we synthesized the title compound, the structure of which is reported here.

The asymmetric unit of the title compound C35H28N4O6S, contains two independent molecules (A and B) with almost identical geometry (Figs. 1 and 2). The central piperidine ring adopts a twisted conformation in both the molecules, as evidenced by the puckering parameters q2 = 0.5497 (2) Å, θ = 36.97 (2)°, φ = 300.8 (3)° and q2 = 0.5441 (17) Å, θ = 143.50 (2)°, φ = 120.4 (3)° for molecule A and B respectively. The 2H-acenaphthylen-1-one ring system (C11A—C22A) and (C11B—C22B) is nearly planar, with a maximum displacement of -0.0635 (3) Å and 0.0755 (2) Å for atom C20A and C20B respectively. In the pyrrolo thiazole ring in both the molecules, the pyrrole ring is in the envelope conformation, and thiazole ring is in twisted envelope conformation with C8A and C8B atoms at the flap in both of these envelopes.The sum of the angles at atom N1A and N1B are 336.20 (11)° and 336.36 (2)° in molecule A and B are in accordance with sp3 -hybridization.The dihedral angle between the nitrophenyl rings in molecule A and B are 76.73 (1)° and 82.93 (1)° respectively these rings are making angles of 44.79 (1)°, 59.27 (1)° and 40.68 (1)°, 57.91 (1)° with the acenaphthene group of molecule A and B respectively.

There are several intramolecular interactions. The C15B—H15B···O3B intermolecular hydrogen bond centrosymmetrically connect two molecules and generate the graph set motif R22(34) (Fig. 3).

Related literature top

For a related structure and background to spiro-pyrrolidine compounds, see: Suresh et al. (2013).

Experimental top

A mixture of 1-methyl-3,5-bis[(E)-4-nitrophenylmethylidene]tetrahydro-4(1H)-pyridinone (1 mmol), acenaphthenequinone (0.182 g, 1 mmol) and 1,3-thiazolane-4-carboxylic acid (0.133 g, 1 mmol) was dissolved in methanol (10 ml) and refluxed for 30 min. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml), the precipitated solid was filtered and washed with water (100 ml) to obtain pure product as pale yellow solid. The product was recrystallized from ethyl acetate solution to obtain colourless blocks. Melting point: 230 °C, yield: 94%

Refinement top

Initial structural solution showed co-crystallized solvent molecule for which a suitable model could not be found. Therefore, the data set was treated with SQUEEZE routine of PLATON (Spek,2009) to model the electron density in the void region. There is one cavity of 833 Å3. The cavity contains approximately 138 electrons which were assigned to the solvent molecule. H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å. Uiso = 1.2Ueq(C) for CH2 and CH groups and Uiso = 1.5Ueq(C) for CH3 group.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (IA), showing 10% probability displacement ellipsoids.
[Figure 2] Fig. 2. The molecular structure of (IB), showing 10% probability displacement ellipsoids.
[Figure 3] Fig. 3. The partial packing diagram of the IB molecule showing the graph set motif R22(34).
5''-(4-Nitrobenzylidene)-7'-(4-nitrophenyl)-1''-methyl-1',3',5',6',7',7a'-hexahydrodispiro[acenaphthylene-1,5'-pyrrolo[1,2-c][1,3]thiazole-6',3''-piperidine]-2,4''(1H)-dione including an unknown solvate top
Crystal data top
C35H28N4O6SZ = 4
Mr = 632.67F(000) = 1320
Triclinic, P1Dx = 1.165 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.1240 (5) ÅCell parameters from 2000 reflections
b = 12.6825 (5) Åθ = 2–27°
c = 25.8778 (11) ŵ = 0.14 mm1
α = 89.823 (4)°T = 293 K
β = 81.185 (2)°Block, colourless
γ = 88.305 (3)°0.30 × 0.27 × 0.25 mm
V = 3606.1 (3) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
15643 independent reflections
Radiation source: fine-focus sealed tube9029 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 0 pixels mm-1θmax = 27.0°, θmin = 1.6°
ω and φ scansh = 1413
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1616
Tmin = 0.960, Tmax = 0.967l = 3231
71136 measured reflections
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0727P)2]
where P = (Fo2 + 2Fc2)/3
15643 reflections(Δ/σ)max = 0.001
831 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C35H28N4O6Sγ = 88.305 (3)°
Mr = 632.67V = 3606.1 (3) Å3
Triclinic, P1Z = 4
a = 11.1240 (5) ÅMo Kα radiation
b = 12.6825 (5) ŵ = 0.14 mm1
c = 25.8778 (11) ÅT = 293 K
α = 89.823 (4)°0.30 × 0.27 × 0.25 mm
β = 81.185 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
15643 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
9029 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.967Rint = 0.040
71136 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.143Δρmax = 0.23 e Å3
S = 1.02Δρmin = 0.26 e Å3
15643 reflectionsAbsolute structure: ?
831 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
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.

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
C1A0.87585 (18)0.70954 (17)0.29382 (7)0.0604 (6)
H1A10.91840.76600.30690.091*
H1A20.83570.73500.26570.091*
H1A30.93280.65360.28130.091*
C1B0.13036 (19)0.72069 (19)0.19002 (8)0.0692 (6)
H1B10.07390.77150.20840.104*
H1B20.17370.68430.21440.104*
H1B30.08680.67090.17270.104*
C2A0.84298 (16)0.63470 (15)0.37957 (7)0.0464 (5)
H2A10.87810.69470.39430.056*
H2A20.90880.58480.36710.056*
C2B0.15413 (17)0.82294 (15)0.11163 (7)0.0487 (5)
H2B10.08670.86690.12850.058*
H2B20.12080.76800.09250.058*
C3A0.75707 (15)0.58349 (13)0.42185 (6)0.0382 (4)
C3B0.23505 (15)0.88878 (13)0.07375 (6)0.0397 (4)
C4A0.64253 (15)0.53868 (13)0.40878 (6)0.0371 (4)
C4B0.34834 (16)0.93051 (14)0.08959 (6)0.0381 (4)
C5A0.59835 (15)0.58108 (13)0.35993 (6)0.0351 (4)
C5B0.39843 (14)0.87307 (13)0.13346 (6)0.0350 (4)
C6A0.71055 (15)0.59021 (14)0.31842 (6)0.0412 (4)
H6A10.75510.52310.31420.049*
H6A20.68670.60990.28510.049*
C6B0.29024 (15)0.84790 (14)0.17458 (6)0.0432 (4)
H6B10.31800.81680.20510.052*
H6B20.24320.91190.18530.052*
C7A0.49715 (15)0.51427 (13)0.34182 (6)0.0386 (4)
H7A0.45430.47960.37290.046*
C7B0.49726 (15)0.93677 (13)0.15573 (6)0.0378 (4)
H7B0.53830.97910.12690.045*
C8A0.41036 (16)0.59708 (14)0.32496 (7)0.0433 (4)
H8A0.44490.62760.29130.052*
C8B0.58715 (15)0.85067 (13)0.16685 (7)0.0398 (4)
H8B0.55410.81010.19780.048*
C9A0.27896 (18)0.57110 (17)0.32504 (9)0.0625 (6)
H9A10.25330.51810.35120.075*
H9A20.26670.54510.29110.075*
C9B0.71781 (16)0.87805 (15)0.16871 (8)0.0510 (5)
H9B10.72920.89510.20410.061*
H9B20.74110.93780.14630.061*
C10A0.32372 (18)0.75971 (16)0.36064 (9)0.0593 (5)
H10A0.35890.80890.33420.071*
H10B0.29970.79730.39340.071*
C10B0.68135 (17)0.70191 (16)0.11956 (8)0.0552 (5)
H10C0.70750.67540.08440.066*
H10D0.64810.64450.14160.066*
C11A0.53387 (15)0.69461 (13)0.37313 (6)0.0379 (4)
C11B0.46986 (15)0.76761 (13)0.11067 (6)0.0369 (4)
C12A0.59294 (16)0.78160 (14)0.33547 (7)0.0444 (4)
C12B0.41528 (17)0.66522 (15)0.13826 (8)0.0506 (5)
C13A0.63341 (17)0.86576 (14)0.36697 (8)0.0493 (5)
C13B0.37407 (18)0.59876 (15)0.09764 (9)0.0559 (5)
C14A0.6892 (2)0.95854 (16)0.35387 (10)0.0683 (6)
H14A0.71030.97820.31910.082*
C14B0.3186 (2)0.50281 (17)0.09947 (12)0.0806 (7)
H14B0.29850.46700.13090.097*
C15A0.7135 (2)1.02295 (18)0.39437 (12)0.0854 (8)
H15A0.75191.08620.38610.102*
C15B0.2937 (3)0.4611 (2)0.05219 (15)0.0987 (10)
H15B0.25650.39630.05280.118*
C16A0.6825 (2)0.99621 (18)0.44620 (11)0.0794 (7)
H16A0.69981.04170.47200.095*
C16B0.3215 (2)0.5114 (2)0.00561 (14)0.0936 (9)
H16B0.30160.48070.02440.112*
C17A0.62507 (19)0.90061 (17)0.46055 (9)0.0609 (6)
C17B0.37991 (19)0.60908 (17)0.00180 (10)0.0653 (6)
C18A0.60165 (16)0.83738 (14)0.41950 (7)0.0458 (4)
C18B0.40406 (16)0.64970 (14)0.04985 (8)0.0483 (5)
C19A0.54073 (16)0.74210 (13)0.42631 (7)0.0399 (4)
C19B0.46462 (15)0.74379 (13)0.05355 (7)0.0393 (4)
C20A0.49753 (17)0.71036 (15)0.47580 (7)0.0497 (5)
H20A0.45230.64980.48160.060*
C20B0.50629 (17)0.79583 (15)0.00874 (7)0.0481 (5)
H20B0.55170.85600.00970.058*
C21A0.5228 (2)0.77132 (18)0.51814 (8)0.0652 (6)
H21A0.49630.74820.55200.078*
C21B0.4802 (2)0.75799 (19)0.03908 (8)0.0661 (6)
H21B0.50630.79560.06940.079*
C22A0.5843 (2)0.86216 (19)0.51140 (9)0.0711 (7)
H22A0.59980.89950.54040.085*
C31A0.77292 (16)0.57557 (14)0.47200 (7)0.0432 (4)
H31A0.71100.54200.49360.052*
C31B0.21664 (16)0.91406 (14)0.02528 (7)0.0451 (4)
H31B0.27660.95580.00730.054*
C32A0.87179 (17)0.61111 (14)0.49840 (7)0.0440 (4)
C32B0.12066 (16)0.88869 (14)0.00463 (7)0.0439 (4)
C33A0.98950 (17)0.63058 (16)0.47390 (7)0.0524 (5)
H33A1.00850.62370.43780.063*
C33B0.14564 (18)0.90447 (18)0.05837 (7)0.0582 (5)
H33B0.22240.92670.07290.070*
C34A1.07798 (18)0.65980 (16)0.50214 (8)0.0558 (5)
H34A1.15590.67390.48530.067*
C34B0.06142 (19)0.88838 (19)0.09054 (8)0.0636 (6)
H34B0.07960.90030.12630.076*
C35A1.05014 (19)0.66777 (16)0.55505 (8)0.0568 (5)
C35B0.05076 (18)0.85414 (16)0.06860 (8)0.0536 (5)
C36A0.9368 (2)0.6493 (2)0.58089 (8)0.0724 (7)
H36A0.92000.65510.61710.087*
C36B0.07985 (18)0.83640 (16)0.01624 (8)0.0577 (5)
H36B0.15630.81270.00230.069*
C37A0.84723 (19)0.62175 (18)0.55242 (8)0.0632 (6)
H37A0.76910.61010.56970.076*
C37B0.00563 (18)0.85414 (16)0.01576 (8)0.0550 (5)
H37B0.01390.84280.05160.066*
C71A0.54515 (16)0.42844 (14)0.30287 (7)0.0413 (4)
C71B0.44803 (15)1.01252 (13)0.19966 (6)0.0394 (4)
C72A0.53556 (19)0.43517 (16)0.25039 (7)0.0550 (5)
H72A0.49680.49380.23790.066*
C72B0.38829 (17)1.10487 (15)0.18855 (8)0.0501 (5)
H72B0.37781.11930.15420.060*
C73A0.5829 (2)0.35578 (18)0.21644 (8)0.0621 (6)
H73A0.57510.36030.18120.074*
C73B0.34393 (18)1.17594 (16)0.22747 (8)0.0562 (5)
H73B0.30331.23770.21970.067*
C74A0.64099 (18)0.27107 (16)0.23445 (8)0.0566 (5)
C74B0.36056 (17)1.15436 (16)0.27766 (8)0.0527 (5)
C75A0.65213 (19)0.26152 (15)0.28631 (8)0.0586 (5)
H75A0.69220.20310.29830.070*
C75B0.42004 (19)1.06533 (17)0.28988 (8)0.0599 (6)
H75B0.43141.05230.32420.072*
C76A0.60285 (18)0.34007 (14)0.32015 (8)0.0513 (5)
H76A0.60840.33370.35550.062*
C76B0.46353 (18)0.99430 (16)0.25079 (7)0.0537 (5)
H76B0.50410.93290.25910.064*
C22B0.4187 (2)0.6692 (2)0.04262 (9)0.0768 (7)
H22B0.40180.64760.07500.092*
N1A0.78620 (13)0.67026 (11)0.33553 (5)0.0418 (4)
N1B0.21612 (13)0.77429 (12)0.15153 (5)0.0450 (4)
N2A1.1455 (2)0.69628 (17)0.58551 (10)0.0790 (6)
N2B0.14135 (18)0.83732 (17)0.10316 (9)0.0706 (5)
N3A0.40829 (13)0.67384 (11)0.36675 (6)0.0426 (4)
N3B0.59309 (12)0.78733 (11)0.11969 (5)0.0399 (3)
N4A0.69134 (19)0.18757 (18)0.19817 (10)0.0772 (6)
N4B0.31700 (18)1.23068 (17)0.31917 (9)0.0731 (6)
O1A0.58766 (12)0.47261 (10)0.43609 (5)0.0520 (3)
O1B0.39758 (12)1.00630 (10)0.06827 (5)0.0541 (3)
O2A1.12997 (19)0.6756 (2)0.63191 (9)0.1399 (10)
O2B0.12558 (16)0.87893 (19)0.14615 (7)0.1109 (7)
O3A1.23600 (18)0.73573 (15)0.56316 (9)0.1026 (6)
O3B0.22908 (17)0.78737 (15)0.08692 (8)0.0953 (6)
O4A0.59126 (12)0.78238 (10)0.28855 (5)0.0558 (4)
O4B0.42138 (13)0.64232 (11)0.18328 (6)0.0669 (4)
O5A0.66833 (18)0.18978 (16)0.15397 (8)0.1059 (7)
O5B0.25968 (19)1.30840 (16)0.30738 (8)0.1013 (6)
O6A0.7540 (2)0.11787 (16)0.21417 (8)0.1069 (7)
O6B0.33981 (19)1.21481 (17)0.36269 (8)0.1094 (7)
S1A0.19481 (5)0.69505 (5)0.34043 (2)0.07070 (18)
S1B0.80665 (5)0.76056 (5)0.14550 (2)0.06367 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0512 (12)0.0823 (15)0.0464 (12)0.0176 (11)0.0003 (9)0.0178 (11)
C1B0.0558 (13)0.0995 (18)0.0534 (13)0.0258 (12)0.0078 (10)0.0315 (12)
C2A0.0404 (11)0.0578 (12)0.0425 (11)0.0058 (9)0.0105 (8)0.0085 (9)
C2B0.0440 (11)0.0610 (12)0.0430 (11)0.0053 (9)0.0127 (9)0.0120 (9)
C3A0.0379 (10)0.0409 (10)0.0363 (10)0.0025 (8)0.0085 (8)0.0038 (8)
C3B0.0401 (10)0.0432 (10)0.0366 (10)0.0035 (8)0.0089 (8)0.0039 (8)
C4A0.0400 (10)0.0371 (9)0.0339 (9)0.0003 (8)0.0053 (8)0.0027 (8)
C4B0.0433 (10)0.0392 (10)0.0314 (9)0.0012 (8)0.0050 (8)0.0013 (8)
C5A0.0379 (10)0.0389 (9)0.0290 (9)0.0024 (7)0.0065 (7)0.0047 (7)
C5B0.0351 (9)0.0396 (9)0.0303 (9)0.0018 (7)0.0050 (7)0.0058 (7)
C6A0.0391 (10)0.0503 (11)0.0337 (9)0.0002 (8)0.0050 (8)0.0032 (8)
C6B0.0391 (10)0.0572 (11)0.0336 (10)0.0014 (9)0.0064 (8)0.0074 (8)
C7A0.0393 (10)0.0425 (10)0.0343 (9)0.0043 (8)0.0062 (8)0.0036 (8)
C7B0.0414 (10)0.0409 (10)0.0318 (9)0.0030 (8)0.0074 (7)0.0034 (7)
C8A0.0404 (11)0.0496 (11)0.0417 (10)0.0037 (8)0.0117 (8)0.0051 (8)
C8B0.0392 (10)0.0453 (10)0.0353 (10)0.0024 (8)0.0072 (8)0.0032 (8)
C9A0.0472 (12)0.0723 (14)0.0723 (14)0.0045 (10)0.0222 (11)0.0021 (11)
C9B0.0445 (11)0.0598 (12)0.0513 (12)0.0056 (9)0.0146 (9)0.0001 (9)
C10A0.0468 (12)0.0631 (13)0.0682 (14)0.0092 (10)0.0111 (10)0.0021 (11)
C10B0.0433 (11)0.0595 (12)0.0629 (13)0.0071 (10)0.0095 (10)0.0095 (10)
C11A0.0366 (10)0.0409 (10)0.0367 (10)0.0003 (8)0.0073 (7)0.0050 (8)
C11B0.0381 (10)0.0370 (9)0.0366 (9)0.0053 (8)0.0080 (8)0.0060 (7)
C12A0.0412 (11)0.0474 (11)0.0447 (12)0.0038 (8)0.0081 (8)0.0092 (9)
C12B0.0430 (11)0.0460 (11)0.0629 (14)0.0001 (9)0.0088 (10)0.0152 (10)
C13A0.0487 (12)0.0425 (11)0.0564 (13)0.0032 (9)0.0067 (9)0.0069 (9)
C13B0.0471 (12)0.0384 (11)0.0829 (16)0.0047 (9)0.0116 (11)0.0029 (10)
C14A0.0778 (16)0.0484 (12)0.0782 (16)0.0148 (11)0.0080 (12)0.0108 (11)
C14B0.0727 (17)0.0467 (13)0.123 (2)0.0125 (12)0.0141 (15)0.0117 (14)
C15A0.0949 (19)0.0524 (14)0.109 (2)0.0266 (13)0.0130 (16)0.0023 (14)
C15B0.085 (2)0.0528 (15)0.163 (3)0.0200 (14)0.031 (2)0.0179 (19)
C16A0.0856 (18)0.0629 (15)0.091 (2)0.0151 (13)0.0153 (15)0.0229 (14)
C16B0.0790 (19)0.0742 (18)0.133 (3)0.0129 (15)0.0315 (18)0.0397 (18)
C17A0.0572 (13)0.0565 (13)0.0689 (15)0.0021 (10)0.0087 (11)0.0160 (11)
C17B0.0527 (13)0.0634 (14)0.0834 (17)0.0029 (11)0.0206 (12)0.0277 (13)
C18A0.0427 (11)0.0431 (10)0.0515 (12)0.0007 (8)0.0078 (9)0.0033 (9)
C18B0.0404 (11)0.0436 (11)0.0617 (13)0.0005 (9)0.0103 (9)0.0068 (10)
C19A0.0397 (10)0.0420 (10)0.0378 (10)0.0029 (8)0.0061 (8)0.0010 (8)
C19B0.0380 (10)0.0389 (10)0.0418 (10)0.0014 (8)0.0084 (8)0.0016 (8)
C20A0.0512 (12)0.0538 (11)0.0420 (11)0.0014 (9)0.0005 (9)0.0003 (9)
C20B0.0468 (11)0.0559 (12)0.0409 (11)0.0027 (9)0.0039 (9)0.0030 (9)
C21A0.0663 (15)0.0847 (16)0.0420 (12)0.0004 (13)0.0002 (10)0.0082 (11)
C21B0.0675 (15)0.0894 (17)0.0411 (12)0.0001 (13)0.0079 (10)0.0089 (11)
C22A0.0726 (16)0.0831 (17)0.0568 (15)0.0037 (13)0.0064 (12)0.0263 (13)
C31A0.0410 (11)0.0501 (11)0.0389 (10)0.0006 (8)0.0077 (8)0.0040 (8)
C31B0.0430 (11)0.0529 (11)0.0395 (10)0.0005 (9)0.0075 (8)0.0064 (8)
C32A0.0478 (11)0.0491 (11)0.0373 (10)0.0015 (9)0.0135 (8)0.0010 (8)
C32B0.0410 (11)0.0545 (11)0.0369 (10)0.0035 (9)0.0090 (8)0.0060 (8)
C33A0.0454 (12)0.0690 (13)0.0437 (11)0.0005 (10)0.0102 (9)0.0001 (10)
C33B0.0441 (12)0.0905 (16)0.0409 (11)0.0071 (11)0.0086 (9)0.0071 (11)
C34A0.0442 (12)0.0647 (13)0.0597 (14)0.0019 (10)0.0121 (10)0.0016 (10)
C34B0.0500 (13)0.1034 (18)0.0383 (11)0.0004 (12)0.0102 (10)0.0022 (11)
C35A0.0483 (13)0.0630 (13)0.0634 (14)0.0015 (10)0.0225 (11)0.0150 (10)
C35B0.0484 (12)0.0630 (13)0.0533 (13)0.0027 (10)0.0213 (10)0.0023 (10)
C36A0.0607 (15)0.1137 (19)0.0450 (12)0.0002 (13)0.0145 (11)0.0198 (13)
C36B0.0415 (12)0.0729 (14)0.0595 (14)0.0029 (10)0.0105 (10)0.0166 (11)
C37A0.0496 (13)0.0968 (17)0.0439 (12)0.0055 (12)0.0083 (10)0.0068 (11)
C37B0.0474 (12)0.0749 (14)0.0428 (11)0.0025 (10)0.0081 (9)0.0130 (10)
C71A0.0421 (10)0.0438 (10)0.0394 (10)0.0080 (8)0.0098 (8)0.0003 (8)
C71B0.0396 (10)0.0425 (10)0.0370 (10)0.0041 (8)0.0078 (8)0.0012 (8)
C72A0.0649 (13)0.0593 (12)0.0424 (11)0.0002 (10)0.0131 (10)0.0013 (9)
C72B0.0521 (12)0.0522 (12)0.0473 (11)0.0052 (9)0.0134 (9)0.0006 (9)
C73A0.0674 (15)0.0776 (15)0.0418 (12)0.0062 (12)0.0091 (10)0.0118 (11)
C73B0.0503 (12)0.0494 (12)0.0681 (14)0.0073 (9)0.0082 (10)0.0041 (10)
C74A0.0477 (12)0.0579 (13)0.0627 (14)0.0091 (10)0.0016 (10)0.0169 (11)
C74B0.0458 (12)0.0564 (12)0.0545 (13)0.0036 (10)0.0027 (9)0.0165 (10)
C75A0.0598 (13)0.0470 (12)0.0700 (15)0.0019 (10)0.0139 (11)0.0072 (10)
C75B0.0687 (14)0.0718 (15)0.0388 (11)0.0062 (12)0.0089 (10)0.0075 (10)
C76A0.0610 (13)0.0492 (11)0.0461 (11)0.0011 (10)0.0155 (9)0.0014 (9)
C76B0.0666 (14)0.0543 (12)0.0407 (11)0.0096 (10)0.0114 (9)0.0024 (9)
C22B0.0753 (17)0.103 (2)0.0538 (15)0.0009 (15)0.0166 (12)0.0275 (14)
N1A0.0395 (8)0.0510 (9)0.0350 (8)0.0079 (7)0.0047 (7)0.0110 (7)
N1B0.0397 (9)0.0588 (10)0.0371 (8)0.0105 (7)0.0064 (7)0.0152 (7)
N2A0.0638 (14)0.0927 (15)0.0870 (17)0.0066 (12)0.0328 (13)0.0310 (13)
N2B0.0539 (12)0.0891 (14)0.0738 (14)0.0004 (11)0.0263 (11)0.0032 (11)
N3A0.0387 (9)0.0451 (9)0.0452 (9)0.0016 (7)0.0106 (7)0.0019 (7)
N3B0.0362 (8)0.0457 (8)0.0384 (8)0.0005 (7)0.0071 (6)0.0036 (7)
N4A0.0627 (14)0.0795 (15)0.0840 (16)0.0135 (11)0.0084 (11)0.0309 (13)
N4B0.0649 (13)0.0738 (14)0.0754 (15)0.0028 (11)0.0064 (11)0.0255 (12)
O1A0.0633 (9)0.0539 (8)0.0423 (7)0.0178 (7)0.0164 (6)0.0154 (6)
O1B0.0700 (9)0.0492 (8)0.0473 (8)0.0158 (7)0.0205 (7)0.0167 (6)
O2A0.0940 (15)0.256 (3)0.0801 (14)0.0194 (17)0.0434 (12)0.0372 (17)
O2B0.0825 (13)0.193 (2)0.0666 (12)0.0259 (13)0.0385 (10)0.0241 (13)
O3A0.0700 (13)0.1102 (15)0.1352 (17)0.0202 (11)0.0359 (12)0.0274 (13)
O3B0.0745 (12)0.1022 (14)0.1211 (15)0.0273 (11)0.0493 (11)0.0252 (11)
O4A0.0629 (9)0.0641 (9)0.0424 (8)0.0019 (7)0.0142 (6)0.0193 (6)
O4B0.0657 (10)0.0726 (10)0.0646 (10)0.0073 (8)0.0165 (8)0.0375 (8)
O5A0.1053 (15)0.1330 (17)0.0745 (12)0.0017 (12)0.0022 (11)0.0495 (12)
O5B0.1089 (15)0.0783 (12)0.1069 (14)0.0171 (11)0.0114 (11)0.0293 (11)
O6A0.1124 (16)0.0786 (13)0.1235 (17)0.0196 (12)0.0020 (13)0.0353 (12)
O6B0.1292 (17)0.1325 (17)0.0642 (12)0.0185 (13)0.0105 (11)0.0436 (12)
S1A0.0415 (3)0.0895 (4)0.0832 (4)0.0091 (3)0.0184 (3)0.0034 (3)
S1B0.0408 (3)0.0819 (4)0.0697 (4)0.0081 (3)0.0144 (3)0.0131 (3)
Geometric parameters (Å, º) top
C1A—N1A1.451 (2)C15A—H15A0.9300
C1A—H1A10.9600C15B—C16B1.359 (4)
C1A—H1A20.9600C15B—H15B0.9300
C1A—H1A30.9600C16A—C17A1.410 (3)
C1B—N1B1.452 (2)C16A—H16A0.9300
C1B—H1B10.9600C16B—C17B1.413 (3)
C1B—H1B20.9600C16B—H16B0.9300
C1B—H1B30.9600C17A—C18A1.394 (3)
C2A—N1A1.450 (2)C17A—C22A1.415 (3)
C2A—C3A1.498 (2)C17B—C22B1.397 (3)
C2A—H2A10.9700C17B—C18B1.414 (3)
C2A—H2A20.9700C18A—C19A1.400 (2)
C2B—N1B1.453 (2)C18B—C19B1.398 (2)
C2B—C3B1.496 (2)C19A—C20A1.361 (2)
C2B—H2B10.9700C19B—C20B1.358 (2)
C2B—H2B20.9700C20A—C21A1.411 (3)
C3A—C31A1.339 (2)C20A—H20A0.9300
C3A—C4A1.496 (2)C20B—C21B1.403 (3)
C3B—C31B1.338 (2)C20B—H20B0.9300
C3B—C4B1.495 (2)C21A—C22A1.354 (3)
C4A—O1A1.2119 (19)C21A—H21A0.9300
C4A—C5A1.516 (2)C21B—C22B1.346 (3)
C4B—O1B1.210 (2)C21B—H21B0.9300
C4B—C5B1.515 (2)C22A—H22A0.9300
C5A—C6A1.524 (2)C31A—C32A1.463 (2)
C5A—C7A1.557 (2)C31A—H31A0.9300
C5A—C11A1.604 (2)C31B—C32B1.455 (2)
C5B—C6B1.520 (2)C31B—H31B0.9300
C5B—C7B1.563 (2)C32A—C37A1.389 (3)
C5B—C11B1.602 (2)C32A—C33A1.393 (3)
C6A—N1A1.450 (2)C32B—C37B1.390 (3)
C6A—H6A10.9700C32B—C33B1.391 (3)
C6A—H6A20.9700C33A—C34A1.372 (3)
C6B—N1B1.451 (2)C33A—H33A0.9300
C6B—H6B10.9700C33B—C34B1.365 (3)
C6B—H6B20.9700C33B—H33B0.9300
C7A—C8A1.514 (2)C34A—C35A1.360 (3)
C7A—C71A1.515 (2)C34A—H34A0.9300
C7A—H7A0.9800C34B—C35B1.372 (3)
C7B—C8B1.516 (2)C34B—H34B0.9300
C7B—C71B1.517 (2)C35A—C36A1.360 (3)
C7B—H7B0.9800C35A—N2A1.469 (3)
C8A—N3A1.454 (2)C35B—C36B1.364 (3)
C8A—C9A1.507 (3)C35B—N2B1.467 (3)
C8A—H8A0.9800C36A—C37A1.380 (3)
C8B—N3B1.455 (2)C36A—H36A0.9300
C8B—C9B1.512 (2)C36B—C37B1.377 (3)
C8B—H8B0.9800C36B—H36B0.9300
C9A—S1A1.819 (2)C37A—H37A0.9300
C9A—H9A10.9700C37B—H37B0.9300
C9A—H9A20.9700C71A—C72A1.381 (2)
C9B—S1B1.815 (2)C71A—C76A1.382 (2)
C9B—H9B10.9700C71B—C76B1.378 (2)
C9B—H9B20.9700C71B—C72B1.381 (2)
C10A—N3A1.442 (2)C72A—C73A1.377 (3)
C10A—S1A1.818 (2)C72A—H72A0.9300
C10A—H10A0.9700C72B—C73B1.377 (3)
C10A—H10B0.9700C72B—H72B0.9300
C10B—N3B1.440 (2)C73A—C74A1.355 (3)
C10B—S1B1.8160 (19)C73A—H73A0.9300
C10B—H10C0.9700C73B—C74B1.365 (3)
C10B—H10D0.9700C73B—H73B0.9300
C11A—N3A1.463 (2)C74A—C75A1.371 (3)
C11A—C19A1.517 (2)C74A—N4A1.458 (3)
C11A—C12A1.562 (2)C74B—C75B1.353 (3)
C11B—N3B1.454 (2)C74B—N4B1.465 (3)
C11B—C19B1.520 (2)C75A—C76A1.373 (3)
C11B—C12B1.572 (2)C75A—H75A0.9300
C12A—O4A1.217 (2)C75B—C76B1.378 (3)
C12A—C13A1.467 (3)C75B—H75B0.9300
C12B—O4B1.211 (2)C76A—H76A0.9300
C12B—C13B1.484 (3)C76B—H76B0.9300
C13A—C14A1.364 (3)C22B—H22B0.9300
C13A—C18A1.400 (3)N2A—O3A1.203 (3)
C13B—C14B1.378 (3)N2A—O2A1.215 (3)
C13B—C18B1.392 (3)N2B—O3B1.200 (2)
C14A—C15A1.394 (3)N2B—O2B1.220 (2)
C14A—H14A0.9300N4A—O5A1.210 (3)
C14B—C15B1.404 (4)N4A—O6A1.220 (3)
C14B—H14B0.9300N4B—O6B1.207 (3)
C15A—C16A1.377 (3)N4B—O5B1.221 (3)
N1A—C1A—H1A1109.5C15A—C16A—H16A119.6
N1A—C1A—H1A2109.5C17A—C16A—H16A119.6
H1A1—C1A—H1A2109.5C15B—C16B—C17B121.5 (3)
N1A—C1A—H1A3109.5C15B—C16B—H16B119.2
H1A1—C1A—H1A3109.5C17B—C16B—H16B119.2
H1A2—C1A—H1A3109.5C18A—C17A—C16A116.0 (2)
N1B—C1B—H1B1109.5C18A—C17A—C22A115.68 (19)
N1B—C1B—H1B2109.5C16A—C17A—C22A128.3 (2)
H1B1—C1B—H1B2109.5C22B—C17B—C16B129.0 (2)
N1B—C1B—H1B3109.5C22B—C17B—C18B116.23 (19)
H1B1—C1B—H1B3109.5C16B—C17B—C18B114.7 (3)
H1B2—C1B—H1B3109.5C17A—C18A—C13A122.60 (18)
N1A—C2A—C3A113.67 (14)C17A—C18A—C19A123.98 (19)
N1A—C2A—H2A1108.8C13A—C18A—C19A113.37 (16)
C3A—C2A—H2A1108.8C13B—C18B—C19B113.45 (17)
N1A—C2A—H2A2108.8C13B—C18B—C17B123.68 (19)
C3A—C2A—H2A2108.8C19B—C18B—C17B122.8 (2)
H2A1—C2A—H2A2107.7C20A—C19A—C18A118.58 (17)
N1B—C2B—C3B113.39 (14)C20A—C19A—C11A132.23 (16)
N1B—C2B—H2B1108.9C18A—C19A—C11A109.16 (15)
C3B—C2B—H2B1108.9C20B—C19B—C18B118.34 (17)
N1B—C2B—H2B2108.9C20B—C19B—C11B132.19 (15)
C3B—C2B—H2B2108.9C18B—C19B—C11B109.47 (15)
H2B1—C2B—H2B2107.7C19A—C20A—C21A118.58 (19)
C31A—C3A—C4A115.76 (15)C19A—C20A—H20A120.7
C31A—C3A—C2A125.07 (16)C21A—C20A—H20A120.7
C4A—C3A—C2A119.16 (14)C19B—C20B—C21B119.37 (18)
C31B—C3B—C4B115.16 (16)C19B—C20B—H20B120.3
C31B—C3B—C2B125.78 (16)C21B—C20B—H20B120.3
C4B—C3B—C2B119.06 (14)C22A—C21A—C20A122.6 (2)
O1A—C4A—C3A121.60 (15)C22A—C21A—H21A118.7
O1A—C4A—C5A121.95 (15)C20A—C21A—H21A118.7
C3A—C4A—C5A116.45 (14)C22B—C21B—C20B122.4 (2)
O1B—C4B—C3B121.51 (15)C22B—C21B—H21B118.8
O1B—C4B—C5B121.76 (15)C20B—C21B—H21B118.8
C3B—C4B—C5B116.73 (15)C21A—C22A—C17A120.5 (2)
C4A—C5A—C6A106.64 (13)C21A—C22A—H22A119.8
C4A—C5A—C7A113.46 (13)C17A—C22A—H22A119.8
C6A—C5A—C7A113.25 (13)C3A—C31A—C32A130.52 (17)
C4A—C5A—C11A108.48 (12)C3A—C31A—H31A114.7
C6A—C5A—C11A110.76 (13)C32A—C31A—H31A114.7
C7A—C5A—C11A104.21 (12)C3B—C31B—C32B132.21 (18)
C4B—C5B—C6B106.88 (13)C3B—C31B—H31B113.9
C4B—C5B—C7B112.59 (13)C32B—C31B—H31B113.9
C6B—C5B—C7B113.10 (13)C37A—C32A—C33A117.70 (16)
C4B—C5B—C11B109.06 (13)C37A—C32A—C31A117.09 (17)
C6B—C5B—C11B111.25 (13)C33A—C32A—C31A125.14 (16)
C7B—C5B—C11B103.97 (12)C37B—C32B—C33B117.44 (17)
N1A—C6A—C5A107.80 (13)C37B—C32B—C31B126.05 (16)
N1A—C6A—H6A1110.1C33B—C32B—C31B116.47 (17)
C5A—C6A—H6A1110.1C34A—C33A—C32A121.15 (18)
N1A—C6A—H6A2110.1C34A—C33A—H33A119.4
C5A—C6A—H6A2110.1C32A—C33A—H33A119.4
H6A1—C6A—H6A2108.5C34B—C33B—C32B122.27 (19)
N1B—C6B—C5B107.67 (13)C34B—C33B—H33B118.9
N1B—C6B—H6B1110.2C32B—C33B—H33B118.9
C5B—C6B—H6B1110.2C35A—C34A—C33A119.05 (19)
N1B—C6B—H6B2110.2C35A—C34A—H34A120.5
C5B—C6B—H6B2110.2C33A—C34A—H34A120.5
H6B1—C6B—H6B2108.5C33B—C34B—C35B118.15 (18)
C8A—C7A—C71A117.52 (14)C33B—C34B—H34B120.9
C8A—C7A—C5A103.12 (13)C35B—C34B—H34B120.9
C71A—C7A—C5A113.92 (14)C36A—C35A—C34A122.13 (18)
C8A—C7A—H7A107.2C36A—C35A—N2A118.7 (2)
C71A—C7A—H7A107.2C34A—C35A—N2A119.2 (2)
C5A—C7A—H7A107.2C36B—C35B—C34B122.09 (18)
C8B—C7B—C71B117.92 (14)C36B—C35B—N2B119.8 (2)
C8B—C7B—C5B102.36 (13)C34B—C35B—N2B118.10 (19)
C71B—C7B—C5B114.82 (14)C35A—C36A—C37A118.85 (19)
C8B—C7B—H7B107.0C35A—C36A—H36A120.6
C71B—C7B—H7B107.0C37A—C36A—H36A120.6
C5B—C7B—H7B107.0C35B—C36B—C37B119.07 (19)
N3A—C8A—C9A105.06 (15)C35B—C36B—H36B120.5
N3A—C8A—C7A100.15 (13)C37B—C36B—H36B120.5
C9A—C8A—C7A119.57 (16)C36A—C37A—C32A121.1 (2)
N3A—C8A—H8A110.4C36A—C37A—H37A119.4
C9A—C8A—H8A110.4C32A—C37A—H37A119.4
C7A—C8A—H8A110.4C36B—C37B—C32B120.98 (18)
N3B—C8B—C9B104.42 (14)C36B—C37B—H37B119.5
N3B—C8B—C7B100.06 (12)C32B—C37B—H37B119.5
C9B—C8B—C7B119.34 (15)C72A—C71A—C76A118.22 (17)
N3B—C8B—H8B110.7C72A—C71A—C7A122.83 (16)
C9B—C8B—H8B110.7C76A—C71A—C7A118.94 (15)
C7B—C8B—H8B110.7C76B—C71B—C72B117.98 (16)
C8A—C9A—S1A104.85 (14)C76B—C71B—C7B122.36 (16)
C8A—C9A—H9A1110.8C72B—C71B—C7B119.64 (15)
S1A—C9A—H9A1110.8C73A—C72A—C71A120.48 (19)
C8A—C9A—H9A2110.8C73A—C72A—H72A119.8
S1A—C9A—H9A2110.8C71A—C72A—H72A119.8
H9A1—C9A—H9A2108.9C73B—C72B—C71B121.05 (18)
C8B—C9B—S1B104.97 (12)C73B—C72B—H72B119.5
C8B—C9B—H9B1110.8C71B—C72B—H72B119.5
S1B—C9B—H9B1110.8C74A—C73A—C72A119.84 (19)
C8B—C9B—H9B2110.8C74A—C73A—H73A120.1
S1B—C9B—H9B2110.8C72A—C73A—H73A120.1
H9B1—C9B—H9B2108.8C74B—C73B—C72B119.02 (19)
N3A—C10A—S1A103.77 (13)C74B—C73B—H73B120.5
N3A—C10A—H10A111.0C72B—C73B—H73B120.5
S1A—C10A—H10A111.0C73A—C74A—C75A121.34 (18)
N3A—C10A—H10B111.0C73A—C74A—N4A119.5 (2)
S1A—C10A—H10B111.0C75A—C74A—N4A119.2 (2)
H10A—C10A—H10B109.0C75B—C74B—C73B121.55 (18)
N3B—C10B—S1B104.06 (12)C75B—C74B—N4B118.8 (2)
N3B—C10B—H10C110.9C73B—C74B—N4B119.6 (2)
S1B—C10B—H10C110.9C74A—C75A—C76A118.6 (2)
N3B—C10B—H10D110.9C74A—C75A—H75A120.7
S1B—C10B—H10D110.9C76A—C75A—H75A120.7
H10C—C10B—H10D109.0C74B—C75B—C76B119.11 (19)
N3A—C11A—C19A111.57 (14)C74B—C75B—H75B120.4
N3A—C11A—C12A113.36 (13)C76B—C75B—H75B120.4
C19A—C11A—C12A101.75 (13)C75A—C76A—C71A121.53 (18)
N3A—C11A—C5A101.21 (12)C75A—C76A—H76A119.2
C19A—C11A—C5A117.74 (13)C71A—C76A—H76A119.2
C12A—C11A—C5A111.73 (13)C75B—C76B—C71B121.29 (19)
N3B—C11B—C19B111.98 (13)C75B—C76B—H76B119.4
N3B—C11B—C12B113.71 (14)C71B—C76B—H76B119.4
C19B—C11B—C12B101.67 (13)C21B—C22B—C17B120.7 (2)
N3B—C11B—C5B101.68 (12)C21B—C22B—H22B119.7
C19B—C11B—C5B115.73 (13)C17B—C22B—H22B119.7
C12B—C11B—C5B112.59 (13)C2A—N1A—C6A111.74 (14)
O4A—C12A—C13A127.13 (17)C2A—N1A—C1A111.07 (14)
O4A—C12A—C11A123.82 (16)C6A—N1A—C1A113.39 (14)
C13A—C12A—C11A108.54 (15)C6B—N1B—C1B113.20 (14)
O4B—C12B—C13B127.88 (18)C6B—N1B—C2B112.52 (14)
O4B—C12B—C11B123.96 (17)C1B—N1B—C2B110.65 (15)
C13B—C12B—C11B107.59 (16)O3A—N2A—O2A123.5 (2)
C14A—C13A—C18A120.52 (19)O3A—N2A—C35A118.6 (2)
C14A—C13A—C12A132.42 (19)O2A—N2A—C35A117.8 (2)
C18A—C13A—C12A107.05 (16)O3B—N2B—O2B123.6 (2)
C14B—C13B—C18B119.7 (2)O3B—N2B—C35B118.4 (2)
C14B—C13B—C12B132.8 (2)O2B—N2B—C35B117.8 (2)
C18B—C13B—C12B107.44 (16)C10A—N3A—C8A110.40 (14)
C13A—C14A—C15A117.8 (2)C10A—N3A—C11A120.56 (14)
C13A—C14A—H14A121.1C8A—N3A—C11A108.50 (13)
C15A—C14A—H14A121.1C10B—N3B—C11B120.76 (14)
C13B—C14B—C15B117.5 (3)C10B—N3B—C8B110.51 (13)
C13B—C14B—H14B121.2C11B—N3B—C8B108.83 (13)
C15B—C14B—H14B121.2O5A—N4A—O6A123.0 (2)
C16A—C15A—C14A122.4 (2)O5A—N4A—C74A118.9 (2)
C16A—C15A—H15A118.8O6A—N4A—C74A118.1 (2)
C14A—C15A—H15A118.8O6B—N4B—O5B123.4 (2)
C16B—C15B—C14B122.8 (2)O6B—N4B—C74B119.2 (2)
C16B—C15B—H15B118.6O5B—N4B—C74B117.4 (2)
C14B—C15B—H15B118.6C10A—S1A—C9A93.73 (9)
C15A—C16A—C17A120.7 (2)C9B—S1B—C10B93.57 (8)
N1A—C2A—C3A—C31A156.81 (17)C13B—C18B—C19B—C20B175.10 (17)
N1A—C2A—C3A—C4A21.9 (2)C17B—C18B—C19B—C20B2.8 (3)
N1B—C2B—C3B—C31B157.16 (17)C13B—C18B—C19B—C11B5.0 (2)
N1B—C2B—C3B—C4B22.0 (2)C17B—C18B—C19B—C11B177.08 (17)
C31A—C3A—C4A—O1A21.9 (2)N3B—C11B—C19B—C20B52.4 (2)
C2A—C3A—C4A—O1A159.25 (16)C12B—C11B—C19B—C20B174.10 (19)
C31A—C3A—C4A—C5A157.53 (15)C5B—C11B—C19B—C20B63.5 (2)
C2A—C3A—C4A—C5A21.3 (2)N3B—C11B—C19B—C18B127.78 (15)
C31B—C3B—C4B—O1B22.4 (2)C12B—C11B—C19B—C18B6.03 (18)
C2B—C3B—C4B—O1B158.36 (17)C5B—C11B—C19B—C18B116.32 (16)
C31B—C3B—C4B—C5B157.45 (15)C18A—C19A—C20A—C21A4.0 (3)
C2B—C3B—C4B—C5B21.8 (2)C11A—C19A—C20A—C21A177.93 (18)
O1A—C4A—C5A—C6A138.97 (16)C18B—C19B—C20B—C21B4.4 (3)
C3A—C4A—C5A—C6A41.59 (18)C11B—C19B—C20B—C21B175.47 (18)
O1A—C4A—C5A—C7A13.6 (2)C19A—C20A—C21A—C22A2.6 (3)
C3A—C4A—C5A—C7A166.97 (13)C19B—C20B—C21B—C22B2.5 (3)
O1A—C4A—C5A—C11A101.69 (18)C20A—C21A—C22A—C17A0.7 (4)
C3A—C4A—C5A—C11A77.74 (17)C18A—C17A—C22A—C21A2.3 (3)
O1B—C4B—C5B—C6B138.27 (16)C16A—C17A—C22A—C21A175.3 (2)
C3B—C4B—C5B—C6B41.90 (18)C4A—C3A—C31A—C32A179.26 (17)
O1B—C4B—C5B—C7B13.5 (2)C2A—C3A—C31A—C32A0.5 (3)
C3B—C4B—C5B—C7B166.67 (14)C4B—C3B—C31B—C32B179.15 (18)
O1B—C4B—C5B—C11B101.37 (18)C2B—C3B—C31B—C32B0.0 (3)
C3B—C4B—C5B—C11B78.47 (17)C3A—C31A—C32A—C37A160.6 (2)
C4A—C5A—C6A—N1A65.84 (17)C3A—C31A—C32A—C33A22.4 (3)
C7A—C5A—C6A—N1A168.66 (13)C3B—C31B—C32B—C37B18.9 (3)
C11A—C5A—C6A—N1A52.00 (17)C3B—C31B—C32B—C33B163.6 (2)
C4B—C5B—C6B—N1B65.10 (17)C37A—C32A—C33A—C34A0.3 (3)
C7B—C5B—C6B—N1B170.44 (13)C31A—C32A—C33A—C34A177.38 (18)
C11B—C5B—C6B—N1B53.86 (17)C37B—C32B—C33B—C34B0.8 (3)
C4A—C5A—C7A—C8A139.87 (14)C31B—C32B—C33B—C34B176.9 (2)
C6A—C5A—C7A—C8A98.37 (16)C32A—C33A—C34A—C35A1.2 (3)
C11A—C5A—C7A—C8A22.07 (16)C32B—C33B—C34B—C35B0.9 (3)
C4A—C5A—C7A—C71A91.65 (17)C33A—C34A—C35A—C36A1.0 (3)
C6A—C5A—C7A—C71A30.1 (2)C33A—C34A—C35A—N2A178.38 (19)
C11A—C5A—C7A—C71A150.56 (14)C33B—C34B—C35B—C36B0.2 (3)
C4B—C5B—C7B—C8B142.61 (14)C33B—C34B—C35B—N2B179.7 (2)
C6B—C5B—C7B—C8B96.09 (16)C34A—C35A—C36A—C37A0.1 (4)
C11B—C5B—C7B—C8B24.71 (15)N2A—C35A—C36A—C37A179.5 (2)
C4B—C5B—C7B—C71B88.38 (17)C34B—C35B—C36B—C37B0.5 (3)
C6B—C5B—C7B—C71B32.91 (19)N2B—C35B—C36B—C37B179.00 (18)
C11B—C5B—C7B—C71B153.71 (14)C35A—C36A—C37A—C32A1.1 (4)
C71A—C7A—C8A—N3A168.08 (14)C33A—C32A—C37A—C36A0.9 (3)
C5A—C7A—C8A—N3A41.87 (16)C31A—C32A—C37A—C36A176.4 (2)
C71A—C7A—C8A—C9A78.0 (2)C35B—C36B—C37B—C32B0.6 (3)
C5A—C7A—C8A—C9A155.76 (16)C33B—C32B—C37B—C36B0.0 (3)
C71B—C7B—C8B—N3B170.29 (14)C31B—C32B—C37B—C36B177.42 (18)
C5B—C7B—C8B—N3B43.25 (15)C8A—C7A—C71A—C72A14.7 (2)
C71B—C7B—C8B—C9B76.8 (2)C5A—C7A—C71A—C72A106.05 (19)
C5B—C7B—C8B—C9B156.20 (15)C8A—C7A—C71A—C76A166.37 (16)
N3A—C8A—C9A—S1A36.67 (17)C5A—C7A—C71A—C76A72.9 (2)
C7A—C8A—C9A—S1A147.91 (14)C8B—C7B—C71B—C76B12.5 (2)
N3B—C8B—C9B—S1B37.70 (16)C5B—C7B—C71B—C76B108.31 (19)
C7B—C8B—C9B—S1B148.29 (13)C8B—C7B—C71B—C72B165.65 (16)
C4A—C5A—C11A—N3A115.31 (14)C5B—C7B—C71B—C72B73.6 (2)
C6A—C5A—C11A—N3A127.98 (13)C76A—C71A—C72A—C73A0.3 (3)
C7A—C5A—C11A—N3A5.87 (15)C7A—C71A—C72A—C73A178.71 (17)
C4A—C5A—C11A—C19A6.54 (19)C76B—C71B—C72B—C73B0.9 (3)
C6A—C5A—C11A—C19A110.18 (16)C7B—C71B—C72B—C73B179.14 (16)
C7A—C5A—C11A—C19A127.71 (15)C71A—C72A—C73A—C74A1.0 (3)
C4A—C5A—C11A—C12A123.75 (15)C71B—C72B—C73B—C74B0.5 (3)
C6A—C5A—C11A—C12A7.03 (18)C72A—C73A—C74A—C75A1.1 (3)
C7A—C5A—C11A—C12A115.08 (14)C72A—C73A—C74A—N4A179.73 (18)
C4B—C5B—C11B—N3B117.27 (14)C72B—C73B—C74B—C75B0.4 (3)
C6B—C5B—C11B—N3B125.09 (13)C72B—C73B—C74B—N4B178.22 (17)
C7B—C5B—C11B—N3B3.05 (15)C73A—C74A—C75A—C76A0.0 (3)
C4B—C5B—C11B—C19B4.32 (18)N4A—C74A—C75A—C76A179.13 (17)
C6B—C5B—C11B—C19B113.32 (15)C73B—C74B—C75B—C76B0.8 (3)
C7B—C5B—C11B—C19B124.64 (14)N4B—C74B—C75B—C76B178.62 (18)
C4B—C5B—C11B—C12B120.67 (15)C74A—C75A—C76A—C71A1.3 (3)
C6B—C5B—C11B—C12B3.02 (18)C72A—C71A—C76A—C75A1.4 (3)
C7B—C5B—C11B—C12B119.01 (14)C7A—C71A—C76A—C75A177.58 (16)
N3A—C11A—C12A—O4A49.7 (2)C74B—C75B—C76B—C71B0.3 (3)
C19A—C11A—C12A—O4A169.64 (17)C72B—C71B—C76B—C75B0.5 (3)
C5A—C11A—C12A—O4A63.9 (2)C7B—C71B—C76B—C75B178.70 (17)
N3A—C11A—C12A—C13A122.68 (16)C20B—C21B—C22B—C17B1.3 (4)
C19A—C11A—C12A—C13A2.76 (18)C16B—C17B—C22B—C21B175.7 (2)
C5A—C11A—C12A—C13A123.73 (15)C18B—C17B—C22B—C21B2.9 (3)
N3B—C11B—C12B—O4B46.3 (2)C3A—C2A—N1A—C6A46.7 (2)
C19B—C11B—C12B—O4B166.82 (18)C3A—C2A—N1A—C1A174.37 (15)
C5B—C11B—C12B—O4B68.7 (2)C5A—C6A—N1A—C2A70.98 (17)
N3B—C11B—C12B—C13B125.69 (16)C5A—C6A—N1A—C1A162.57 (15)
C19B—C11B—C12B—C13B5.15 (18)C5B—C6B—N1B—C1B163.39 (16)
C5B—C11B—C12B—C13B119.33 (15)C5B—C6B—N1B—C2B70.25 (18)
O4A—C12A—C13A—C14A7.6 (4)C3B—C2B—N1B—C6B46.4 (2)
C11A—C12A—C13A—C14A179.7 (2)C3B—C2B—N1B—C1B174.13 (16)
O4A—C12A—C13A—C18A170.98 (18)C36A—C35A—N2A—O3A163.2 (2)
C11A—C12A—C13A—C18A1.1 (2)C34A—C35A—N2A—O3A17.4 (3)
O4B—C12B—C13B—C14B9.5 (4)C36A—C35A—N2A—O2A19.0 (3)
C11B—C12B—C13B—C14B178.9 (2)C34A—C35A—N2A—O2A160.4 (2)
O4B—C12B—C13B—C18B168.95 (19)C36B—C35B—N2B—O3B15.8 (3)
C11B—C12B—C13B—C18B2.6 (2)C34B—C35B—N2B—O3B164.7 (2)
C18A—C13A—C14A—C15A0.3 (3)C36B—C35B—N2B—O2B161.2 (2)
C12A—C13A—C14A—C15A178.7 (2)C34B—C35B—N2B—O2B18.4 (3)
C18B—C13B—C14B—C15B0.6 (3)S1A—C10A—N3A—C8A40.47 (17)
C12B—C13B—C14B—C15B178.9 (2)S1A—C10A—N3A—C11A168.26 (12)
C13A—C14A—C15A—C16A0.4 (4)C9A—C8A—N3A—C10A52.04 (19)
C13B—C14B—C15B—C16B0.2 (4)C7A—C8A—N3A—C10A176.61 (14)
C14A—C15A—C16A—C17A0.6 (4)C9A—C8A—N3A—C11A173.81 (15)
C14B—C15B—C16B—C17B1.2 (5)C7A—C8A—N3A—C11A49.25 (16)
C15A—C16A—C17A—C18A0.5 (3)C19A—C11A—N3A—C10A71.2 (2)
C15A—C16A—C17A—C22A178.1 (2)C12A—C11A—N3A—C10A43.0 (2)
C15B—C16B—C17B—C22B177.5 (3)C5A—C11A—N3A—C10A162.77 (15)
C15B—C16B—C17B—C18B1.1 (4)C19A—C11A—N3A—C8A160.18 (14)
C16A—C17A—C18A—C13A0.4 (3)C12A—C11A—N3A—C8A85.66 (17)
C22A—C17A—C18A—C13A178.31 (19)C5A—C11A—N3A—C8A34.13 (16)
C16A—C17A—C18A—C19A177.18 (19)S1B—C10B—N3B—C11B168.56 (12)
C22A—C17A—C18A—C19A0.8 (3)S1B—C10B—N3B—C8B39.99 (17)
C14A—C13A—C18A—C17A0.3 (3)C19B—C11B—N3B—C10B74.39 (19)
C12A—C13A—C18A—C17A179.05 (17)C12B—C11B—N3B—C10B40.2 (2)
C14A—C13A—C18A—C19A177.52 (18)C5B—C11B—N3B—C10B161.46 (14)
C12A—C13A—C18A—C19A1.3 (2)C19B—C11B—N3B—C8B156.29 (13)
C14B—C13B—C18B—C19B177.28 (19)C12B—C11B—N3B—C8B89.15 (17)
C12B—C13B—C18B—C19B1.4 (2)C5B—C11B—N3B—C8B32.14 (16)
C14B—C13B—C18B—C17B0.6 (3)C9B—C8B—N3B—C10B52.20 (18)
C12B—C13B—C18B—C17B179.30 (18)C7B—C8B—N3B—C10B176.23 (14)
C22B—C17B—C18B—C13B178.52 (19)C9B—C8B—N3B—C11B173.01 (14)
C16B—C17B—C18B—C13B0.3 (3)C7B—C8B—N3B—C11B48.99 (16)
C22B—C17B—C18B—C19B0.8 (3)C73A—C74A—N4A—O5A8.3 (3)
C16B—C17B—C18B—C19B177.97 (19)C75A—C74A—N4A—O5A170.9 (2)
C17A—C18A—C19A—C20A2.5 (3)C73A—C74A—N4A—O6A172.5 (2)
C13A—C18A—C19A—C20A175.29 (16)C75A—C74A—N4A—O6A8.3 (3)
C17A—C18A—C19A—C11A179.08 (17)C75B—C74B—N4B—O6B3.3 (3)
C13A—C18A—C19A—C11A3.2 (2)C73B—C74B—N4B—O6B174.6 (2)
N3A—C11A—C19A—C20A53.5 (2)C75B—C74B—N4B—O5B177.3 (2)
C12A—C11A—C19A—C20A174.70 (19)C73B—C74B—N4B—O5B4.8 (3)
C5A—C11A—C19A—C20A62.8 (3)N3A—C10A—S1A—C9A14.43 (15)
N3A—C11A—C19A—C18A124.66 (15)C8A—C9A—S1A—C10A12.82 (16)
C12A—C11A—C19A—C18A3.49 (18)C8B—C9B—S1B—C10B14.16 (14)
C5A—C11A—C19A—C18A118.97 (16)N3B—C10B—S1B—C9B13.34 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8B—H8B···O4A0.982.473.270 (2)139
C72A—H72A···O4B0.932.553.461 (2)167
C76B—H76B···O4A0.932.303.222 (2)174
C15B—H15B···O3Bi0.932.503.343 (3)151
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC35H28N4O6S
Mr632.67
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.1240 (5), 12.6825 (5), 25.8778 (11)
α, β, γ (°)89.823 (4), 81.185 (2), 88.305 (3)
V3)3606.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.30 × 0.27 × 0.25
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.960, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
71136, 15643, 9029
Rint0.040
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.143, 1.02
No. of reflections15643
No. of parameters831
No. of restraints0
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.26

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8B—H8B···O4A0.982.473.270 (2)139
C72A—H72A···O4B0.932.553.461 (2)167
C76B—H76B···O4A0.932.303.222 (2)174
C15B—H15B···O3Bi0.932.503.343 (3)151
Symmetry code: (i) x, y+1, z.
Acknowledgements top

JS thanks the UGC for the FIST support. JS and RV thank the management of the Madura College for their encouragement and support. RRK thanksthe DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009)

references
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