supplementary materials


hg5152 scheme

Acta Cryst. (2012). E68, o103    [ doi:10.1107/S1600536811052731 ]

1-Benzyl-3-methyl-3',5'-diphenylspiro[quinoxaline-2(1H),2'(3'H)-1,3,4-thiadiazole]

C. A. Anothane, R. Bouhfid, E. M. Essassi and S. W. Ng

Abstract top

In the title spiro compound, C29H24N4S, the quinoxaline and thiadiazole ring systems share a common C atom; their mean planes are aligned at 87.0 (1)° in one molecule and at 84.1 (1)° in the other independent molecule. The thiazole ring possesses two aromatic ring substituents and is roughly coplanar with these rings [the dihedral angles between the thiadiazole and phenyl rings are 10.7 (1) and 11.7 (1)° in one molecule, and 16.8 (1) and 17.7 (1)° in the other]. The aromatic ring of the benzyl unit of one molecule is disordered over two orientations in a 1:1 ratio.

Comment top

A previous study reported 1-allyl-3-methyl-3',5'-diphenylspiro[quinoxaline-2(1H),2'(3'H)-[1,3,4]thiadiazole] (Anothane et al., 2010). The allyl substitutent is replaced by a benzyl substituent in the present study. The asymmetric unit of C29H24N4S (Scheme I) consists of two independent molecules, one of which is disordered in the benzyl substituent. The quinoxaline and thiadiazole ring systems share a common C atom; their mean planes are aligned at 87.0 (1)° in one molecule (Fig.1 ) and at 84.1 (1)° in the other independent molecule (Fig. 2). The thiazole ring possesses two aromatic ring substituents and is nearly coplanar with these rings. The aromatic ring of the benzyl unit of one molecule is disordered over two positions in a 1:1 ratio.

Related literature top

For a related molecule, see: Anothane et al. (2010).

Experimental top

To a solution of1-benzyl-3-methylquinoxaline-2-thione (1 g, 3.75 mmole) and diphenylnitrilimine (1.28 g, 5.55 mmole) in THF (20 mL), was added triethylamine (0.78 ml, 5.55 mmol). The mixture was heated under reflux for 24 hours. The precipitate was recovered by filtration and was separated by chromatography on silica gel (hexane/ethylAcetate: 9/1). Colorless crystals were isolated when solvent was allowed to evaporate.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

One of the phenyl rings of the second independent molecule is disordered over two positions in 1:1 ratio. The ring was refined as a rigid hexagon of 1.39 Å sides. The temperature factors of the primed atoms were set to those of the unprimed ones, and all anisotropic temperature factors were restrained to be nearly isotropic. The pair of Cbenzyl–Cphenyl distances were restrained to within 0.01 Å of each other.

Omitted were (0 1 1), (0 1 1), (1 0 0) and (1 1 1).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of one C29H24N4S molecule at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of second C29H24N4S molecule at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the phenyl ring is now shown.
1-benzyl-3-methyl-3',5'-diphenyl-1H,3'H-spiro[quinoxaline-2,2'- [1,3,4]thiadiazole] top
Crystal data top
C29H24N4SZ = 4
Mr = 460.58F(000) = 968
Triclinic, P1Dx = 1.284 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.5441 (2) ÅCell parameters from 9950 reflections
b = 14.8971 (2) Åθ = 2.5–30.7°
c = 15.0149 (2) ŵ = 0.16 mm1
α = 66.431 (1)°T = 293 K
β = 63.921 (1)°Prism, colorless
γ = 65.275 (1)°0.35 × 0.34 × 0.17 mm
V = 2383.45 (6) Å3
Data collection top
Bruker APEX DUO
diffractometer
14918 independent reflections
Radiation source: fine-focus sealed tube10508 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 30.8°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.946, Tmax = 0.973k = 2121
69257 measured reflectionsl = 2121
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.5234P]
where P = (Fo2 + 2Fc2)/3
14918 reflections(Δ/σ)max = 0.001
609 parametersΔρmax = 0.27 e Å3
37 restraintsΔρmin = 0.22 e Å3
Crystal data top
C29H24N4Sγ = 65.275 (1)°
Mr = 460.58V = 2383.45 (6) Å3
Triclinic, P1Z = 4
a = 13.5441 (2) ÅMo Kα radiation
b = 14.8971 (2) ŵ = 0.16 mm1
c = 15.0149 (2) ÅT = 293 K
α = 66.431 (1)°0.35 × 0.34 × 0.17 mm
β = 63.921 (1)°
Data collection top
Bruker APEX DUO
diffractometer
10508 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Rint = 0.030
Tmin = 0.946, Tmax = 0.973θmax = 30.8°
69257 measured reflectionsStandard reflections: 0
14918 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.135Δρmax = 0.27 e Å3
S = 1.01Δρmin = 0.22 e Å3
14918 reflectionsAbsolute structure: ?
609 parametersFlack parameter: ?
37 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S11.03210 (3)0.16041 (3)0.12571 (3)0.04354 (9)
S20.00042 (3)0.90325 (3)0.39048 (3)0.04801 (10)
N10.83510 (11)0.22867 (9)0.36228 (9)0.0460 (3)
N20.79303 (10)0.23285 (9)0.19279 (8)0.0422 (2)
N30.90581 (10)0.34954 (9)0.08824 (8)0.0424 (2)
N40.98330 (10)0.33516 (8)0.00567 (8)0.0392 (2)
N50.19751 (10)0.90389 (9)0.14100 (8)0.0417 (2)
N60.20056 (9)0.74996 (8)0.32571 (8)0.0363 (2)
N70.01669 (9)0.74698 (8)0.34166 (8)0.0382 (2)
N80.06977 (10)0.74838 (9)0.43523 (9)0.0420 (2)
C10.76113 (13)0.17803 (10)0.37494 (10)0.0432 (3)
C20.70620 (15)0.12791 (12)0.47415 (11)0.0544 (4)
H20.72060.12780.52930.065*
C30.63089 (18)0.07861 (14)0.49172 (14)0.0682 (5)
H30.59450.04510.55830.082*
C40.60992 (18)0.07943 (15)0.40958 (15)0.0712 (5)
H40.55870.04630.42140.085*
C50.66327 (16)0.12833 (13)0.31002 (13)0.0586 (4)
H50.64810.12770.25560.070*
C60.73990 (12)0.17860 (10)0.29116 (10)0.0420 (3)
C70.97184 (16)0.32273 (14)0.25839 (13)0.0583 (4)
H7A0.97490.31360.32420.087*
H7B0.94320.39450.22760.087*
H7C1.04760.29540.21470.087*
C80.89375 (13)0.26797 (11)0.27174 (10)0.0433 (3)
C90.89281 (12)0.25828 (10)0.17439 (9)0.0382 (3)
C100.78465 (13)0.21995 (13)0.10455 (11)0.0492 (3)
H10A0.80470.14720.11240.059*
H10B0.84120.24650.04260.059*
C110.66866 (12)0.27151 (12)0.08998 (10)0.0444 (3)
C120.59016 (14)0.35441 (14)0.12664 (13)0.0560 (4)
H120.60690.37880.16500.067*
C130.48657 (16)0.40219 (15)0.10738 (15)0.0651 (4)
H130.43400.45770.13340.078*
C140.46113 (17)0.36769 (16)0.04981 (15)0.0681 (5)
H140.39180.39990.03640.082*
C150.53893 (17)0.28544 (16)0.01246 (14)0.0666 (5)
H150.52240.26220.02690.080*
C160.64163 (15)0.23679 (14)0.03277 (12)0.0540 (4)
H160.69310.18030.00790.065*
C170.83014 (12)0.44896 (10)0.09100 (10)0.0396 (3)
C180.73607 (14)0.46811 (13)0.17849 (12)0.0519 (3)
H180.72010.41430.23620.062*
C190.66687 (15)0.56774 (14)0.17868 (14)0.0595 (4)
H190.60440.58030.23700.071*
C200.68894 (15)0.64826 (13)0.09420 (15)0.0604 (4)
H200.64240.71490.09550.073*
C210.78075 (15)0.62907 (12)0.00762 (15)0.0575 (4)
H210.79540.68330.05000.069*
C220.85136 (13)0.53058 (11)0.00511 (12)0.0464 (3)
H220.91300.51880.05390.056*
C231.05153 (11)0.24335 (10)0.00069 (9)0.0368 (3)
C241.13657 (11)0.20878 (10)0.09069 (10)0.0378 (3)
C251.14717 (13)0.27713 (13)0.18831 (11)0.0494 (3)
H251.10340.34550.19530.059*
C261.22270 (15)0.24296 (16)0.27435 (12)0.0630 (4)
H261.22890.28850.33930.076*
C271.28896 (15)0.14228 (16)0.26508 (14)0.0653 (5)
H271.33950.11990.32360.078*
C281.28045 (14)0.07476 (14)0.16929 (14)0.0592 (4)
H281.32610.00690.16300.071*
C291.20409 (12)0.10748 (12)0.08214 (12)0.0464 (3)
H291.19800.06130.01750.056*
C300.28653 (11)0.87214 (10)0.18112 (10)0.0397 (3)
C310.37500 (13)0.91778 (12)0.12528 (13)0.0528 (4)
H310.37370.96730.06330.063*
C320.46396 (14)0.89049 (14)0.16081 (15)0.0618 (4)
H320.52220.92190.12370.074*
C330.46623 (14)0.81610 (14)0.25209 (15)0.0592 (4)
H330.52630.79770.27640.071*
C340.38066 (13)0.76849 (12)0.30798 (13)0.0493 (3)
H340.38410.71790.36900.059*
C350.28904 (11)0.79598 (10)0.27338 (10)0.0373 (3)
C360.01034 (15)0.90929 (12)0.15860 (13)0.0549 (4)
H36A0.02880.95290.08990.082*
H36B0.05790.94660.20220.082*
H36C0.00250.85070.15840.082*
C370.10810 (12)0.87449 (9)0.19810 (10)0.0387 (3)
C380.09188 (11)0.81007 (9)0.30892 (9)0.0349 (2)
C390.19346 (12)0.68252 (11)0.43048 (10)0.0435 (3)
H39A0.11810.67180.46380.052*0.50
H39B0.19960.71770.46910.052*0.50
H39C0.11760.67290.46410.052*0.50
H39D0.20090.71730.46870.052*0.50
C400.2843 (4)0.5780 (3)0.4369 (5)0.0450 (3)0.50
C410.3129 (5)0.5183 (5)0.3729 (4)0.0530 (11)0.50
H410.28020.54380.32130.064*0.50
C420.3902 (6)0.4206 (5)0.3860 (6)0.0691 (12)0.50
H420.40930.38070.34310.083*0.50
C430.4389 (5)0.3825 (3)0.4631 (7)0.0853 (7)0.50
H430.49070.31710.47180.102*0.50
C440.4104 (5)0.4421 (5)0.5271 (5)0.0808 (16)0.50
H440.44300.41670.57870.097*0.50
C450.3330 (4)0.5399 (4)0.5140 (5)0.0592 (11)0.50
H450.31390.57980.55690.071*0.50
C40'0.2816 (4)0.5787 (3)0.4372 (5)0.0450 (3)0.50
C41'0.3403 (5)0.5333 (5)0.3561 (4)0.0530 (11)0.50
H41'0.32910.56890.29270.064*0.50
C42'0.4159 (5)0.4347 (5)0.3696 (6)0.0691 (12)0.50
H42'0.45520.40430.31520.083*0.50
C43'0.4326 (5)0.3815 (3)0.4642 (7)0.0853 (7)0.50
H43'0.48310.31550.47320.102*0.50
C44'0.3738 (5)0.4269 (5)0.5454 (5)0.0808 (16)0.50
H44'0.38510.39130.60870.097*0.50
C45'0.2983 (4)0.5255 (4)0.5319 (4)0.0592 (11)0.50
H45'0.25900.55580.58620.071*0.50
C460.05731 (12)0.65744 (9)0.30806 (10)0.0373 (3)
C470.13942 (13)0.65090 (11)0.21192 (11)0.0441 (3)
H470.16960.70530.16940.053*
C480.17631 (14)0.56422 (12)0.17923 (12)0.0508 (3)
H480.23000.56130.11430.061*
C490.13428 (18)0.48211 (12)0.24180 (13)0.0617 (4)
H490.16040.42320.22030.074*
C500.05311 (19)0.48863 (13)0.33660 (13)0.0657 (5)
H500.02430.43340.37910.079*
C510.01315 (15)0.57533 (11)0.37033 (11)0.0510 (4)
H510.04290.57870.43420.061*
C520.08744 (12)0.82234 (10)0.46872 (11)0.0431 (3)
C530.17437 (13)0.83765 (11)0.56788 (11)0.0500 (3)
C540.26402 (16)0.79480 (15)0.61287 (15)0.0689 (5)
H540.26980.75670.58010.083*
C550.3453 (2)0.80904 (18)0.70713 (17)0.0888 (7)
H550.40580.78070.73720.107*
C560.3365 (2)0.86476 (19)0.75598 (17)0.0921 (8)
H560.39070.87350.81930.111*
C570.2486 (2)0.90736 (18)0.71186 (16)0.0849 (7)
H570.24320.94510.74530.102*
C580.16709 (17)0.89472 (14)0.61754 (14)0.0643 (4)
H580.10770.92440.58760.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.04818 (19)0.03957 (17)0.03708 (16)0.01054 (14)0.01453 (14)0.00653 (13)
S20.0507 (2)0.03946 (18)0.0531 (2)0.01480 (15)0.00821 (16)0.01978 (15)
N10.0593 (7)0.0467 (6)0.0350 (5)0.0181 (6)0.0160 (5)0.0105 (5)
N20.0467 (6)0.0550 (7)0.0311 (5)0.0223 (5)0.0101 (4)0.0124 (5)
N30.0486 (6)0.0376 (6)0.0320 (5)0.0109 (5)0.0085 (5)0.0079 (4)
N40.0421 (6)0.0409 (6)0.0326 (5)0.0144 (5)0.0095 (4)0.0086 (4)
N50.0503 (6)0.0379 (6)0.0376 (5)0.0180 (5)0.0151 (5)0.0047 (4)
N60.0397 (5)0.0362 (5)0.0328 (5)0.0117 (4)0.0140 (4)0.0059 (4)
N70.0415 (6)0.0347 (5)0.0390 (5)0.0169 (4)0.0087 (4)0.0094 (4)
N80.0395 (6)0.0409 (6)0.0402 (6)0.0136 (5)0.0080 (5)0.0093 (5)
C10.0519 (8)0.0386 (7)0.0360 (6)0.0124 (6)0.0125 (6)0.0099 (5)
C20.0698 (10)0.0470 (8)0.0361 (7)0.0185 (7)0.0136 (7)0.0041 (6)
C30.0809 (12)0.0593 (10)0.0493 (9)0.0349 (9)0.0102 (9)0.0025 (8)
C40.0826 (13)0.0679 (11)0.0652 (11)0.0481 (10)0.0167 (10)0.0005 (9)
C50.0699 (11)0.0620 (10)0.0531 (9)0.0361 (9)0.0184 (8)0.0083 (7)
C60.0479 (7)0.0397 (7)0.0364 (6)0.0160 (6)0.0099 (5)0.0093 (5)
C70.0686 (10)0.0716 (11)0.0526 (9)0.0344 (9)0.0224 (8)0.0159 (8)
C80.0527 (8)0.0463 (7)0.0366 (6)0.0162 (6)0.0168 (6)0.0121 (5)
C90.0444 (7)0.0397 (6)0.0317 (5)0.0149 (5)0.0120 (5)0.0085 (5)
C100.0470 (8)0.0714 (10)0.0379 (7)0.0210 (7)0.0100 (6)0.0234 (7)
C110.0477 (7)0.0595 (8)0.0309 (6)0.0263 (7)0.0086 (5)0.0101 (6)
C120.0569 (9)0.0674 (10)0.0564 (9)0.0200 (8)0.0198 (7)0.0253 (8)
C130.0589 (10)0.0691 (11)0.0743 (11)0.0128 (8)0.0252 (9)0.0280 (9)
C140.0612 (11)0.0815 (13)0.0730 (12)0.0186 (9)0.0338 (9)0.0205 (10)
C150.0703 (11)0.0897 (13)0.0622 (10)0.0301 (10)0.0287 (9)0.0265 (10)
C160.0580 (9)0.0695 (10)0.0453 (8)0.0243 (8)0.0145 (7)0.0222 (7)
C170.0416 (7)0.0397 (6)0.0440 (7)0.0107 (5)0.0176 (5)0.0145 (5)
C180.0545 (9)0.0536 (8)0.0476 (8)0.0132 (7)0.0124 (7)0.0212 (7)
C190.0548 (9)0.0656 (10)0.0650 (10)0.0061 (8)0.0177 (8)0.0383 (9)
C200.0597 (10)0.0470 (8)0.0863 (12)0.0005 (7)0.0355 (9)0.0318 (9)
C210.0612 (10)0.0408 (8)0.0745 (11)0.0120 (7)0.0313 (9)0.0118 (7)
C220.0468 (8)0.0419 (7)0.0527 (8)0.0137 (6)0.0196 (6)0.0102 (6)
C230.0378 (6)0.0404 (6)0.0344 (6)0.0152 (5)0.0119 (5)0.0081 (5)
C240.0340 (6)0.0462 (7)0.0382 (6)0.0159 (5)0.0106 (5)0.0128 (5)
C250.0475 (8)0.0547 (8)0.0405 (7)0.0149 (7)0.0120 (6)0.0102 (6)
C260.0568 (10)0.0858 (13)0.0388 (7)0.0252 (9)0.0062 (7)0.0154 (8)
C270.0481 (9)0.0910 (14)0.0580 (10)0.0188 (9)0.0023 (7)0.0398 (10)
C280.0446 (8)0.0620 (10)0.0713 (11)0.0082 (7)0.0118 (7)0.0340 (9)
C290.0414 (7)0.0483 (8)0.0500 (8)0.0134 (6)0.0136 (6)0.0148 (6)
C300.0408 (7)0.0393 (6)0.0398 (6)0.0145 (5)0.0086 (5)0.0136 (5)
C310.0495 (8)0.0525 (8)0.0532 (8)0.0238 (7)0.0053 (7)0.0147 (7)
C320.0431 (8)0.0649 (10)0.0795 (12)0.0243 (7)0.0055 (8)0.0286 (9)
C330.0407 (8)0.0648 (10)0.0830 (12)0.0115 (7)0.0214 (8)0.0326 (9)
C340.0446 (8)0.0521 (8)0.0575 (8)0.0105 (6)0.0212 (7)0.0194 (7)
C350.0374 (6)0.0378 (6)0.0397 (6)0.0105 (5)0.0105 (5)0.0161 (5)
C360.0633 (10)0.0492 (8)0.0608 (9)0.0228 (7)0.0374 (8)0.0029 (7)
C370.0480 (7)0.0314 (6)0.0395 (6)0.0138 (5)0.0192 (5)0.0044 (5)
C380.0379 (6)0.0307 (6)0.0369 (6)0.0118 (5)0.0119 (5)0.0082 (5)
C390.0476 (7)0.0452 (7)0.0324 (6)0.0100 (6)0.0151 (5)0.0070 (5)
C400.0494 (8)0.0423 (7)0.0388 (6)0.0112 (6)0.0173 (6)0.0056 (5)
C410.053 (3)0.0546 (19)0.0449 (18)0.0114 (15)0.0151 (18)0.0131 (14)
C420.070 (3)0.0560 (18)0.067 (2)0.0065 (16)0.015 (2)0.0238 (18)
C430.0932 (16)0.0511 (10)0.0841 (14)0.0059 (10)0.0393 (13)0.0088 (10)
C440.095 (4)0.062 (2)0.068 (2)0.001 (2)0.047 (3)0.0011 (16)
C450.072 (3)0.0533 (17)0.046 (2)0.0124 (17)0.027 (2)0.0057 (15)
C40'0.0494 (8)0.0423 (7)0.0388 (6)0.0112 (6)0.0173 (6)0.0056 (5)
C41'0.053 (3)0.0546 (19)0.0449 (18)0.0114 (15)0.0151 (18)0.0131 (14)
C42'0.070 (3)0.0560 (18)0.067 (2)0.0065 (16)0.015 (2)0.0238 (18)
C43'0.0932 (16)0.0511 (10)0.0841 (14)0.0059 (10)0.0393 (13)0.0088 (10)
C44'0.095 (4)0.062 (2)0.068 (2)0.001 (2)0.047 (3)0.0011 (16)
C45'0.072 (3)0.0533 (17)0.046 (2)0.0124 (17)0.027 (2)0.0057 (15)
C460.0468 (7)0.0329 (6)0.0382 (6)0.0134 (5)0.0196 (5)0.0069 (5)
C470.0515 (8)0.0409 (7)0.0431 (7)0.0173 (6)0.0150 (6)0.0108 (5)
C480.0623 (9)0.0488 (8)0.0474 (8)0.0124 (7)0.0212 (7)0.0190 (6)
C490.0979 (14)0.0410 (8)0.0591 (9)0.0187 (8)0.0360 (9)0.0158 (7)
C500.1113 (15)0.0430 (8)0.0541 (9)0.0393 (9)0.0283 (10)0.0048 (7)
C510.0756 (10)0.0437 (7)0.0401 (7)0.0295 (7)0.0189 (7)0.0044 (6)
C520.0410 (7)0.0385 (7)0.0426 (7)0.0088 (5)0.0107 (5)0.0103 (5)
C530.0476 (8)0.0418 (7)0.0430 (7)0.0038 (6)0.0091 (6)0.0108 (6)
C540.0635 (11)0.0617 (11)0.0612 (10)0.0210 (9)0.0015 (8)0.0188 (8)
C550.0759 (14)0.0783 (14)0.0714 (13)0.0273 (11)0.0134 (10)0.0182 (11)
C560.0928 (17)0.0832 (15)0.0558 (11)0.0134 (13)0.0087 (11)0.0263 (11)
C570.0926 (16)0.0863 (15)0.0602 (11)0.0065 (12)0.0130 (11)0.0392 (11)
C580.0647 (10)0.0639 (10)0.0544 (9)0.0073 (8)0.0138 (8)0.0250 (8)
Geometric parameters (Å, °) top
S1—C231.7614 (13)C27—H270.9300
S1—C91.8863 (14)C28—C291.385 (2)
S2—C521.7571 (14)C28—H280.9300
S2—C381.8837 (13)C29—H290.9300
N1—C81.2748 (18)C30—C311.3941 (19)
N1—C11.3997 (19)C30—C351.3998 (18)
N2—C61.3964 (17)C31—C321.372 (2)
N2—C91.4360 (17)C31—H310.9300
N2—C101.4696 (17)C32—C331.379 (3)
N3—N41.3741 (15)C32—H320.9300
N3—C171.4098 (17)C33—C341.381 (2)
N3—C91.4650 (16)C33—H330.9300
N4—C231.2844 (17)C34—C351.3961 (19)
N5—C371.2744 (17)C34—H340.9300
N5—C301.4050 (18)C36—C371.4979 (19)
N6—C351.3973 (16)C36—H36A0.9600
N6—C381.4405 (16)C36—H36B0.9600
N6—C391.4755 (16)C36—H36C0.9600
N7—N81.3792 (15)C37—C381.5218 (17)
N7—C461.4200 (16)C39—C40'1.505 (4)
N7—C381.4674 (15)C39—C401.526 (4)
N8—C521.2810 (18)C39—H39A0.9700
C1—C21.390 (2)C39—H39B0.9700
C1—C61.4045 (19)C39—H39C0.9700
C2—C31.373 (3)C39—H39D0.9700
C2—H20.9300C40—C411.3900
C3—C41.376 (3)C40—C451.3900
C3—H30.9300C41—C421.3900
C4—C51.381 (2)C41—H410.9300
C4—H40.9300C42—C431.3900
C5—C61.393 (2)C42—H420.9300
C5—H50.9300C43—C441.3900
C7—C81.493 (2)C43—H430.9300
C7—H7A0.9600C44—C451.3900
C7—H7B0.9600C44—H440.9300
C7—H7C0.9600C45—H450.9300
C8—C91.5311 (17)C40'—C41'1.3900
C10—C111.505 (2)C40'—C45'1.3900
C10—H10A0.9700C41'—C42'1.3900
C10—H10B0.9700C41'—H41'0.9300
C11—C121.374 (2)C42'—C43'1.3900
C11—C161.389 (2)C42'—H42'0.9300
C12—C131.384 (2)C43'—C44'1.3900
C12—H120.9300C43'—H43'0.9300
C13—C141.377 (3)C44'—C45'1.3900
C13—H130.9300C44'—H44'0.9300
C14—C151.370 (3)C45'—H45'0.9300
C14—H140.9300C46—C511.3906 (18)
C15—C161.381 (2)C46—C471.3930 (19)
C15—H150.9300C47—C481.382 (2)
C16—H160.9300C47—H470.9300
C17—C221.392 (2)C48—C491.377 (2)
C17—C181.398 (2)C48—H480.9300
C18—C191.385 (2)C49—C501.375 (3)
C18—H180.9300C49—H490.9300
C19—C201.374 (3)C50—C511.384 (2)
C19—H190.9300C50—H500.9300
C20—C211.377 (3)C51—H510.9300
C20—H200.9300C52—C531.4699 (19)
C21—C221.381 (2)C53—C541.386 (2)
C21—H210.9300C53—C581.389 (2)
C22—H220.9300C54—C551.391 (3)
C23—C241.4675 (18)C54—H540.9300
C24—C291.387 (2)C55—C561.374 (4)
C24—C251.3963 (19)C55—H550.9300
C25—C261.379 (2)C56—C571.365 (4)
C25—H250.9300C56—H560.9300
C26—C271.375 (3)C57—C581.387 (3)
C26—H260.9300C57—H570.9300
C27—C281.374 (3)C58—H580.9300
C23—S1—C989.54 (6)C32—C31—H31119.6
C52—S2—C3889.22 (6)C30—C31—H31119.6
C8—N1—C1119.26 (12)C31—C32—C33119.40 (15)
C6—N2—C9119.25 (11)C31—C32—H32120.3
C6—N2—C10118.00 (11)C33—C32—H32120.3
C9—N2—C10116.44 (10)C32—C33—C34121.01 (15)
N4—N3—C17117.47 (10)C32—C33—H33119.5
N4—N3—C9117.73 (10)C34—C33—H33119.5
C17—N3—C9123.78 (11)C33—C34—C35120.31 (15)
C23—N4—N3112.64 (10)C33—C34—H34119.8
C37—N5—C30118.41 (11)C35—C34—H34119.8
C35—N6—C38116.56 (10)C34—C35—N6123.09 (12)
C35—N6—C39117.82 (11)C34—C35—C30118.51 (13)
C38—N6—C39115.50 (10)N6—C35—C30118.40 (11)
N8—N7—C46116.60 (10)C37—C36—H36A109.5
N8—N7—C38116.70 (10)C37—C36—H36B109.5
C46—N7—C38120.87 (10)H36A—C36—H36B109.5
C52—N8—N7112.79 (11)C37—C36—H36C109.5
C2—C1—N1118.06 (13)H36A—C36—H36C109.5
C2—C1—C6119.99 (14)H36B—C36—H36C109.5
N1—C1—C6121.93 (12)N5—C37—C36119.71 (12)
C3—C2—C1120.80 (16)N5—C37—C38122.79 (12)
C3—C2—H2119.6C36—C37—C38117.38 (12)
C1—C2—H2119.6N6—C38—N7112.12 (10)
C2—C3—C4119.17 (16)N6—C38—C37111.60 (10)
C2—C3—H3120.4N7—C38—C37111.89 (10)
C4—C3—H3120.4N6—C38—S2113.51 (8)
C3—C4—C5121.48 (17)N7—C38—S2101.45 (8)
C3—C4—H4119.3C37—C38—S2105.72 (8)
C5—C4—H4119.3N6—C39—C40'115.8 (3)
C4—C5—C6119.91 (16)N6—C39—C40115.6 (3)
C4—C5—H5120.0N6—C39—H39A108.4
C6—C5—H5120.0C40—C39—H39A108.4
C5—C6—N2122.65 (13)N6—C39—H39B108.4
C5—C6—C1118.65 (13)C40—C39—H39B108.4
N2—C6—C1118.65 (12)H39A—C39—H39B107.5
C8—C7—H7A109.5N6—C39—H39C108.3
C8—C7—H7B109.5C40'—C39—H39C108.3
H7A—C7—H7B109.5C40—C39—H39C109.2
C8—C7—H7C109.5N6—C39—H39D108.3
H7A—C7—H7C109.5C40'—C39—H39D108.3
H7B—C7—H7C109.5C40—C39—H39D107.7
N1—C8—C7119.18 (12)H39C—C39—H39D107.4
N1—C8—C9123.41 (12)C41—C40—C45120.0
C7—C8—C9117.35 (12)C41—C40—C39121.8 (5)
N2—C9—N3111.50 (11)C45—C40—C39118.0 (5)
N2—C9—C8112.01 (11)C40—C41—C42120.0
N3—C9—C8112.22 (11)C40—C41—H41120.0
N2—C9—S1113.06 (9)C42—C41—H41120.0
N3—C9—S1100.67 (8)C43—C42—C41120.0
C8—C9—S1106.80 (9)C43—C42—H42120.0
N2—C10—C11115.34 (12)C41—C42—H42120.0
N2—C10—H10A108.4C42—C43—C44120.0
C11—C10—H10A108.4C42—C43—H43120.0
N2—C10—H10B108.4C44—C43—H43120.0
C11—C10—H10B108.4C45—C44—C43120.0
H10A—C10—H10B107.5C45—C44—H44120.0
C12—C11—C16118.34 (14)C43—C44—H44120.0
C12—C11—C10123.07 (13)C44—C45—C40120.0
C16—C11—C10118.52 (14)C44—C45—H45120.0
C11—C12—C13121.00 (15)C40—C45—H45120.0
C11—C12—H12119.5C41'—C40'—C45'120.0
C13—C12—H12119.5C41'—C40'—C39123.1 (5)
C14—C13—C12120.15 (17)C45'—C40'—C39116.8 (5)
C14—C13—H13119.9C42'—C41'—C40'120.0
C12—C13—H13119.9C42'—C41'—H41'120.0
C15—C14—C13119.37 (17)C40'—C41'—H41'120.0
C15—C14—H14120.3C41'—C42'—C43'120.0
C13—C14—H14120.3C41'—C42'—H42'120.0
C14—C15—C16120.58 (16)C43'—C42'—H42'120.0
C14—C15—H15119.7C42'—C43'—C44'120.0
C16—C15—H15119.7C42'—C43'—H43'120.0
C15—C16—C11120.55 (16)C44'—C43'—H43'120.0
C15—C16—H16119.7C45'—C44'—C43'120.0
C11—C16—H16119.7C45'—C44'—H44'120.0
C22—C17—C18119.13 (13)C43'—C44'—H44'120.0
C22—C17—N3119.04 (12)C44'—C45'—C40'120.0
C18—C17—N3121.81 (13)C44'—C45'—H45'120.0
C19—C18—C17119.57 (15)C40'—C45'—H45'120.0
C19—C18—H18120.2C51—C46—C47118.82 (12)
C17—C18—H18120.2C51—C46—N7120.08 (12)
C20—C19—C18121.12 (16)C47—C46—N7121.08 (11)
C20—C19—H19119.4C48—C47—C46120.48 (13)
C18—C19—H19119.4C48—C47—H47119.8
C19—C20—C21119.21 (15)C46—C47—H47119.8
C19—C20—H20120.4C49—C48—C47120.65 (15)
C21—C20—H20120.4C49—C48—H48119.7
C20—C21—C22121.01 (16)C47—C48—H48119.7
C20—C21—H21119.5C50—C49—C48118.86 (14)
C22—C21—H21119.5C50—C49—H49120.6
C21—C22—C17119.94 (15)C48—C49—H49120.6
C21—C22—H22120.0C49—C50—C51121.60 (15)
C17—C22—H22120.0C49—C50—H50119.2
N4—C23—C24122.09 (11)C51—C50—H50119.2
N4—C23—S1115.57 (10)C50—C51—C46119.56 (15)
C24—C23—S1122.28 (10)C50—C51—H51120.2
C29—C24—C25119.00 (13)C46—C51—H51120.2
C29—C24—C23120.89 (12)N8—C52—C53122.12 (13)
C25—C24—C23120.06 (12)N8—C52—S2116.15 (10)
C26—C25—C24119.86 (15)C53—C52—S2121.72 (11)
C26—C25—H25120.1C54—C53—C58119.44 (16)
C24—C25—H25120.1C54—C53—C52120.23 (15)
C27—C26—C25120.69 (16)C58—C53—C52120.33 (15)
C27—C26—H26119.7C53—C54—C55119.8 (2)
C25—C26—H26119.7C53—C54—H54120.1
C28—C27—C26119.90 (15)C55—C54—H54120.1
C28—C27—H27120.0C56—C55—C54120.3 (2)
C26—C27—H27120.0C56—C55—H55119.9
C27—C28—C29120.17 (16)C54—C55—H55119.9
C27—C28—H28119.9C57—C56—C55120.20 (19)
C29—C28—H28119.9C57—C56—H56119.9
C28—C29—C24120.36 (15)C55—C56—H56119.9
C28—C29—H29119.8C56—C57—C58120.5 (2)
C24—C29—H29119.8C56—C57—H57119.8
C31—C30—C35120.04 (13)C58—C57—H57119.8
C31—C30—N5117.99 (13)C57—C58—C53119.9 (2)
C35—C30—N5121.97 (11)C57—C58—H58120.1
C32—C31—C30120.71 (16)C53—C58—H58120.1
C17—N3—N4—C23177.09 (11)C32—C33—C34—C350.8 (2)
C9—N3—N4—C2314.02 (16)C33—C34—C35—N6179.24 (13)
C46—N7—N8—C52168.27 (12)C33—C34—C35—C300.2 (2)
C38—N7—N8—C5214.87 (16)C38—N6—C35—C34154.72 (12)
C8—N1—C1—C2174.26 (14)C39—N6—C35—C3410.82 (18)
C8—N1—C1—C67.0 (2)C38—N6—C35—C3026.29 (16)
N1—C1—C2—C3178.70 (16)C39—N6—C35—C30170.18 (11)
C6—C1—C2—C30.0 (2)C31—C30—C35—C340.84 (19)
C1—C2—C3—C40.1 (3)N5—C30—C35—C34179.82 (12)
C2—C3—C4—C50.3 (3)C31—C30—C35—N6178.21 (12)
C3—C4—C5—C60.3 (3)N5—C30—C35—N60.78 (18)
C4—C5—C6—N2177.38 (17)C30—N5—C37—C36178.37 (13)
C4—C5—C6—C10.1 (3)C30—N5—C37—C382.43 (19)
C9—N2—C6—C5162.95 (14)C35—N6—C38—N7163.42 (10)
C10—N2—C6—C511.8 (2)C39—N6—C38—N751.84 (14)
C9—N2—C6—C119.59 (19)C35—N6—C38—C3737.00 (14)
C10—N2—C6—C1170.72 (13)C39—N6—C38—C37178.26 (10)
C2—C1—C6—C50.0 (2)C35—N6—C38—S282.34 (11)
N1—C1—C6—C5178.63 (14)C39—N6—C38—S262.39 (12)
C2—C1—C6—N2177.62 (14)N8—N7—C38—N6101.30 (12)
N1—C1—C6—N21.1 (2)C46—N7—C38—N650.89 (15)
C1—N1—C8—C7179.48 (14)N8—N7—C38—C37132.44 (11)
C1—N1—C8—C93.3 (2)C46—N7—C38—C3775.37 (14)
C6—N2—C9—N3154.10 (12)N8—N7—C38—S220.15 (12)
C10—N2—C9—N354.32 (16)C46—N7—C38—S2172.34 (9)
C6—N2—C9—C827.40 (17)N5—C37—C38—N626.28 (17)
C10—N2—C9—C8178.98 (12)C36—C37—C38—N6157.69 (12)
C6—N2—C9—S193.32 (12)N5—C37—C38—N7152.83 (12)
C10—N2—C9—S158.26 (14)C36—C37—C38—N731.14 (16)
N4—N3—C9—N299.93 (13)N5—C37—C38—S297.58 (13)
C17—N3—C9—N268.19 (16)C36—C37—C38—S278.45 (13)
N4—N3—C9—C8133.49 (12)C52—S2—C38—N6104.98 (9)
C17—N3—C9—C858.39 (17)C52—S2—C38—N715.49 (9)
N4—N3—C9—S120.24 (13)C52—S2—C38—C37132.37 (9)
C17—N3—C9—S1171.63 (11)C35—N6—C39—C40'74.8 (3)
N1—C8—C9—N220.1 (2)C38—N6—C39—C40'140.9 (3)
C7—C8—C9—N2162.65 (13)C35—N6—C39—C4073.8 (3)
N1—C8—C9—N3146.37 (14)C38—N6—C39—C40141.9 (3)
C7—C8—C9—N336.35 (18)N6—C39—C40—C4144.8 (3)
N1—C8—C9—S1104.23 (15)C40'—C39—C40—C4161 (35)
C7—C8—C9—S173.06 (15)N6—C39—C40—C45139.6 (2)
C23—S1—C9—N2102.97 (9)C40'—C39—C40—C45114 (36)
C23—S1—C9—N316.07 (9)C45—C40—C41—C420.0
C23—S1—C9—C8133.39 (9)C39—C40—C41—C42175.5 (4)
C6—N2—C10—C1173.28 (18)C40—C41—C42—C430.0
C9—N2—C10—C11134.78 (13)C41—C42—C43—C440.0
N2—C10—C11—C1224.2 (2)C42—C43—C44—C450.0
N2—C10—C11—C16158.88 (14)C43—C44—C45—C400.0
C16—C11—C12—C130.1 (2)C41—C40—C45—C440.0
C10—C11—C12—C13177.07 (16)C39—C40—C45—C44175.7 (4)
C11—C12—C13—C140.7 (3)N6—C39—C40'—C41'21.0 (4)
C12—C13—C14—C150.4 (3)C40—C39—C40'—C41'95 (35)
C13—C14—C15—C160.5 (3)N6—C39—C40'—C45'162.5 (2)
C14—C15—C16—C111.1 (3)C40—C39—C40'—C45'88 (36)
C12—C11—C16—C150.8 (2)C45'—C40'—C41'—C42'0.0
C10—C11—C16—C15176.31 (15)C39—C40'—C41'—C42'176.4 (5)
N4—N3—C17—C2212.63 (18)C40'—C41'—C42'—C43'0.0
C9—N3—C17—C22179.22 (12)C41'—C42'—C43'—C44'0.0
N4—N3—C17—C18168.98 (13)C42'—C43'—C44'—C45'0.0
C9—N3—C17—C180.8 (2)C43'—C44'—C45'—C40'0.0
C22—C17—C18—C190.9 (2)C41'—C40'—C45'—C44'0.0
N3—C17—C18—C19177.49 (14)C39—C40'—C45'—C44'176.6 (4)
C17—C18—C19—C200.1 (2)N8—N7—C46—C512.40 (18)
C18—C19—C20—C210.7 (3)C38—N7—C46—C51149.81 (13)
C19—C20—C21—C220.8 (3)N8—N7—C46—C47176.04 (12)
C20—C21—C22—C170.0 (2)C38—N7—C46—C4731.75 (18)
C18—C17—C22—C210.9 (2)C51—C46—C47—C480.1 (2)
N3—C17—C22—C21177.58 (13)N7—C46—C47—C48178.54 (13)
N3—N4—C23—C24176.09 (11)C46—C47—C48—C491.3 (2)
N3—N4—C23—S11.33 (15)C47—C48—C49—C501.4 (3)
C9—S1—C23—N411.29 (11)C48—C49—C50—C510.1 (3)
C9—S1—C23—C24166.12 (11)C49—C50—C51—C461.2 (3)
N4—C23—C24—C29175.80 (12)C47—C46—C51—C501.3 (2)
S1—C23—C24—C291.45 (17)N7—C46—C51—C50179.77 (15)
N4—C23—C24—C251.58 (19)N7—N8—C52—C53178.98 (12)
S1—C23—C24—C25178.82 (11)N7—N8—C52—S20.26 (16)
C29—C24—C25—C261.0 (2)C38—S2—C52—N89.95 (12)
C23—C24—C25—C26176.42 (14)C38—S2—C52—C53168.77 (12)
C24—C25—C26—C270.8 (3)N8—C52—C53—C5420.8 (2)
C25—C26—C27—C280.2 (3)S2—C52—C53—C54160.53 (14)
C26—C27—C28—C291.0 (3)N8—C52—C53—C58158.86 (15)
C27—C28—C29—C240.7 (2)S2—C52—C53—C5819.8 (2)
C25—C24—C29—C280.3 (2)C58—C53—C54—C550.2 (3)
C23—C24—C29—C28177.15 (13)C52—C53—C54—C55179.46 (18)
C37—N5—C30—C31169.58 (13)C53—C54—C55—C560.4 (3)
C37—N5—C30—C3511.42 (19)C54—C55—C56—C570.6 (4)
C35—C30—C31—C321.4 (2)C55—C56—C57—C580.1 (4)
N5—C30—C31—C32179.57 (14)C56—C57—C58—C530.5 (3)
C30—C31—C32—C330.9 (3)C54—C53—C58—C570.7 (3)
C31—C32—C33—C340.2 (3)C52—C53—C58—C57178.99 (17)
Acknowledgements top

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

references
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