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Acta Cryst. (2011). E67, o1022    [ doi:10.1107/S1600536811011391 ]

6-(1-Adamantyl)-3-(2-chlorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

M. N. Tahir, M.-H. Khan, S. Hammed, T. H. Bokhari and S. Hina

Abstract top

In the title compound, C19H19ClN4S, the 2-chlorophenyl and [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole fragments (r.m.s. deviations of 0.015 and 0.017 Å, respectively) are oriented at a dihedral angle of 55.76 (6)°. The adamantane group exhibits extensive rotational disorder about the single C-C bond to the thiadiazole ring, which was modelled as occupying four orientations each with 0.25 occupancy. In the crystal, the chlorophenyl rings exhibit [pi]-[pi] stacking interactions with centroid-centroid distances of 3.9526 (18) Å.

Comment top

The crystal structure of the fluoro analogue of the title compound has been published (Khan et al., 2009). The title molecule is shown in Fig. 1. The adamantyl group is disordered over four positions. The chlorobenzene moiety A (C1—C6/CL1) is planar with r. m. s. deviation of 0.0149 Å, whereas two fused heterocyclic rings B (C7/N1/N2/C8/S1/C9/N4/N3) are also planar with r. m. s. deviation of 0.0166 Å. The dihedral angle beteen A/B is 55.76 (6)°. The value of this dihedral angle in the fluoro isomer is 48.98 (6)°. There exist π—π interaction with the benzene ring centroids at a distance of 3.9526 (18) Å ( symmetry code: i = 1 - x, -y, 1 - z). The crystal structure is mainly stabilized by van der Waals forces.

Related literature top

For background and the structure of the fluoro analogue, see: Khan et al. (2009).

Experimental top

The title compound was prepared from a mixture of 4-amino-5-(2-chlorophenyl)-2H-1,2,4-triazole-3(4H)-thione and adamantane-1-carboxylic acid using the method described by Khan et al. (2009).

Refinement top

The adamantyl group is disordered. It has been modelled in four positions related by rotation around C-C bond to the thiadiazole ring. All atoms of the adamantyl group have been refined isotropically, with a common displacement parameter for the C atoms of each position. Restraints were imposed on 1-2 and 1-3 distances in the adamatyl ring [1.535 (5) and 2.50 (1) Å, respectively]. Equal occupancy factor of 0.25 was assumed for all disordered positions.

The H-atoms were positioned geometrically (C–H = 0.93–0.98 Å) and treated as riding with Uiso(H) = xUeq(C), where x = 1.2 for all H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of of the title compound with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small spheres of arbitrary radius. Only one of the four disordered positions of the adamantyl group is shown.
6-(1-Adamantyl)-3-(2-chlorophenyl)-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole top
Crystal data top
C19H19ClN4SF(000) = 1552
Mr = 370.89Dx = 1.387 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2676 reflections
a = 24.5210 (12) Åθ = 2.5–25.3°
b = 9.1356 (5) ŵ = 0.34 mm−1
c = 19.1943 (16) ÅT = 296 K
β = 124.282 (1)°Prism, colorless
V = 3552.8 (4) Å30.28 × 0.24 × 0.20 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3202 independent reflections
Radiation source: fine-focus sealed tube2676 reflections with I > 2σ(I)
graphiteRint = 0.025
Detector resolution: 8.20 pixels mm-1θmax = 25.3°, θmin = 2.5°
ω scansh = −29→29
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −10→10
Tmin = 0.945, Tmax = 0.956l = −23→19
16675 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0489P)2 + 7.1182P]
where P = (Fo2 + 2Fc2)/3
3202 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.38 e Å−3
84 restraintsΔρmin = −0.39 e Å−3
Crystal data top
C19H19ClN4SV = 3552.8 (4) Å3
Mr = 370.89Z = 8
Monoclinic, C2/cMo Kα radiation
a = 24.5210 (12) ŵ = 0.34 mm−1
b = 9.1356 (5) ÅT = 296 K
c = 19.1943 (16) Å0.28 × 0.24 × 0.20 mm
β = 124.282 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3202 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2676 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.956Rint = 0.025
16675 measured reflectionsθmax = 25.3°
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.125Δρmax = 0.38 e Å−3
S = 1.02Δρmin = −0.39 e Å−3
3202 reflectionsAbsolute structure: ?
257 parametersFlack parameter: ?
84 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/UeqOcc. (<1)
Cl10.42498 (4)−0.09216 (11)0.63099 (6)0.0770 (3)
S10.22506 (3)−0.34790 (7)0.36430 (5)0.0495 (2)
N10.40695 (10)−0.4767 (2)0.50704 (13)0.0461 (5)
N20.34112 (10)−0.5233 (2)0.45569 (14)0.0489 (5)
N30.34555 (9)−0.2822 (2)0.45879 (12)0.0368 (4)
N40.31664 (9)−0.1464 (2)0.43225 (12)0.0396 (5)
C10.46844 (11)−0.2418 (3)0.54892 (15)0.0401 (5)
C20.48003 (13)−0.1275 (3)0.60326 (17)0.0491 (6)
C30.53567 (14)−0.0420 (3)0.6378 (2)0.0650 (8)
H30.54280.03440.67410.078*
C40.58072 (14)−0.0703 (4)0.6184 (2)0.0696 (9)
H40.6180−0.01170.64080.083*
C50.57103 (14)−0.1844 (4)0.5661 (2)0.0637 (8)
H50.6021−0.20400.55400.076*
C60.51534 (12)−0.2698 (3)0.53154 (17)0.0500 (6)
H60.5090−0.34710.49620.060*
C70.40903 (11)−0.3331 (3)0.50811 (14)0.0382 (5)
C80.30660 (12)−0.4025 (3)0.42871 (15)0.0405 (5)
C90.25384 (11)−0.1642 (3)0.38309 (15)0.0386 (5)
C100.20638 (10)−0.0380 (2)0.34271 (13)0.0377 (5)
C110.1416 (3)−0.0728 (7)0.3342 (6)0.0373 (9)*0.25
H11A0.1213−0.15880.29920.045*0.25
H11B0.1507−0.09350.38940.045*0.25
C120.0944 (3)0.0576 (7)0.2947 (6)0.0373 (9)*0.25
H12A0.05230.03410.28680.045*0.25
C130.1255 (4)0.1924 (9)0.3516 (6)0.0373 (9)*0.25
H13A0.13190.17330.40550.045*0.25
H13B0.09580.27510.32580.045*0.25
C140.1920 (3)0.2299 (7)0.3657 (4)0.0373 (9)*0.25
H14A0.21200.31500.40290.045*0.25
C150.2375 (3)0.0958 (6)0.4042 (4)0.0373 (9)*0.25
H15A0.24420.07130.45760.045*0.25
H15B0.28020.11870.41470.045*0.25
C160.1821 (6)0.2592 (12)0.2807 (6)0.0373 (9)*0.25
H16A0.15540.34640.25540.045*0.25
H16B0.22460.27660.28950.045*0.25
C170.1489 (4)0.1321 (10)0.2219 (5)0.0373 (9)*0.25
H17A0.14090.15630.16710.045*0.25
C180.1966 (5)0.0022 (10)0.2603 (4)0.0373 (9)*0.25
H18A0.1787−0.08050.22200.045*0.25
H18B0.23860.02840.26970.045*0.25
C190.0834 (4)0.0920 (13)0.2096 (5)0.0373 (9)*0.25
H19A0.06440.00750.17280.045*0.25
H19B0.05270.17290.18300.045*0.25
C210.1331 (2)−0.0855 (7)0.2940 (6)0.0375 (9)*0.25
H21A0.1236−0.15400.24990.045*0.25
H21B0.1252−0.13500.33230.045*0.25
C220.0868 (3)0.0464 (8)0.2548 (6)0.0375 (9)*0.25
H220.04090.01360.22510.045*0.25
C230.1012 (4)0.1573 (10)0.3227 (6)0.0375 (9)*0.25
H23A0.09380.11270.36260.045*0.25
H23B0.07190.24060.29720.045*0.25
C240.1732 (4)0.2079 (7)0.3686 (4)0.0375 (9)*0.25
H24A0.18270.27950.41210.045*0.25
C250.2187 (4)0.0749 (8)0.4100 (4)0.0375 (9)*0.25
H25A0.21080.02970.44920.045*0.25
H25B0.26440.10670.44140.045*0.25
C260.1824 (5)0.2796 (11)0.3037 (7)0.0375 (9)*0.25
H26A0.15180.36070.27690.045*0.25
H26B0.22690.31790.33190.045*0.25
C270.1704 (4)0.1704 (10)0.2380 (6)0.0375 (9)*0.25
H270.17760.21650.19770.045*0.25
C280.2171 (5)0.0392 (9)0.2801 (5)0.0375 (9)*0.25
H28A0.26250.07260.30970.045*0.25
H28B0.2096−0.02990.23720.045*0.25
C290.0985 (4)0.1168 (12)0.1920 (5)0.0375 (9)*0.25
H29A0.06860.19870.16430.045*0.25
H29B0.08960.04600.14910.045*0.25
C310.1576 (5)−0.0417 (11)0.3677 (8)0.0785 (15)*0.25
H31A0.1812−0.03660.42860.094*0.25
H31B0.1330−0.13280.34900.094*0.25
C320.1099 (4)0.0882 (12)0.3274 (7)0.0785 (15)*0.25
H320.07910.08930.34470.094*0.25
C330.1494 (6)0.2305 (11)0.3531 (9)0.0785 (15)*0.25
H33A0.17510.24040.41390.094*0.25
H33B0.11920.31280.32880.094*0.25
C340.1956 (5)0.2334 (8)0.3235 (8)0.0785 (15)*0.25
H340.21870.32740.33670.094*0.25
C350.2448 (4)0.1059 (7)0.3665 (8)0.0785 (15)*0.25
H35A0.27450.10420.34830.094*0.25
H35B0.27080.11870.42720.094*0.25
C360.1556 (9)0.202 (2)0.2287 (8)0.0785 (15)*0.25
H36A0.12440.28130.19930.094*0.25
H36B0.18540.20180.21060.094*0.25
C370.1198 (6)0.0651 (14)0.2040 (7)0.0785 (15)*0.25
H370.09470.05390.14260.094*0.25
C380.1697 (6)−0.0608 (14)0.2470 (3)0.0785 (15)*0.25
H38A0.1470−0.15430.23080.094*0.25
H38B0.2006−0.05950.23070.094*0.25
C390.0727 (5)0.064 (2)0.2324 (7)0.0785 (15)*0.25
H39A0.04010.14120.20310.094*0.25
H39B0.0497−0.02850.21750.094*0.25
C410.1975 (4)0.0257 (9)0.4083 (4)0.0441 (9)*0.25
H41A0.23980.05760.45690.053*0.25
H41B0.1797−0.04800.42660.053*0.25
C420.1501 (4)0.1560 (8)0.3699 (4)0.0441 (9)*0.25
H420.14390.19890.41180.053*0.25
C430.1781 (5)0.2705 (7)0.3403 (6)0.0441 (9)*0.25
H43A0.22070.30360.38790.053*0.25
H43B0.14870.35430.31750.053*0.25
C440.1860 (4)0.2064 (8)0.2727 (6)0.0441 (9)*0.25
H440.20410.28110.25450.053*0.25
C450.2336 (4)0.0758 (7)0.3108 (6)0.0441 (9)*0.25
H45A0.27680.10870.35720.053*0.25
H45B0.23840.03200.26850.053*0.25
C460.1191 (5)0.1544 (13)0.1969 (6)0.0441 (9)*0.25
H46A0.08900.23680.17200.053*0.25
H46B0.12450.11340.15450.053*0.25
C470.0902 (4)0.0383 (9)0.2250 (5)0.0441 (9)*0.25
H470.04720.00480.17700.053*0.25
C480.1387 (3)−0.0905 (9)0.2653 (5)0.0441 (9)*0.25
H48A0.1449−0.13400.22410.053*0.25
H48B0.1206−0.16470.28300.053*0.25
C490.0839 (4)0.1042 (13)0.2933 (6)0.0441 (9)*0.25
H49A0.05360.18640.26980.053*0.25
H49B0.06530.03150.31110.053*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0670 (5)0.0945 (7)0.0839 (6)−0.0140 (4)0.0512 (5)−0.0385 (5)
S10.0379 (3)0.0375 (4)0.0665 (4)−0.0041 (3)0.0254 (3)0.0007 (3)
N10.0481 (12)0.0389 (12)0.0539 (13)0.0067 (9)0.0302 (10)0.0041 (10)
N20.0478 (12)0.0370 (11)0.0633 (14)0.0022 (9)0.0321 (11)0.0025 (10)
N30.0373 (10)0.0314 (10)0.0416 (10)0.0017 (8)0.0221 (9)0.0017 (8)
N40.0365 (10)0.0327 (10)0.0468 (11)0.0028 (8)0.0218 (9)0.0036 (9)
C10.0353 (12)0.0388 (13)0.0413 (12)0.0075 (10)0.0186 (10)0.0054 (10)
C20.0433 (13)0.0497 (15)0.0520 (15)0.0018 (11)0.0254 (12)−0.0045 (12)
C30.0523 (16)0.0581 (18)0.075 (2)−0.0104 (14)0.0298 (15)−0.0187 (15)
C40.0445 (16)0.067 (2)0.087 (2)−0.0107 (14)0.0306 (16)−0.0064 (17)
C50.0416 (15)0.076 (2)0.077 (2)0.0046 (14)0.0353 (15)0.0031 (17)
C60.0409 (13)0.0523 (16)0.0546 (15)0.0084 (12)0.0255 (12)0.0012 (12)
C70.0384 (12)0.0385 (13)0.0392 (12)0.0061 (10)0.0227 (10)0.0020 (10)
C80.0414 (13)0.0362 (12)0.0482 (14)−0.0020 (10)0.0278 (11)−0.0002 (11)
C90.0377 (12)0.0350 (12)0.0449 (13)−0.0011 (10)0.0244 (11)0.0014 (10)
C100.0327 (11)0.0374 (12)0.0427 (12)0.0016 (9)0.0210 (10)0.0038 (10)
Geometric parameters (Å, °) top
Cl1—C21.737 (3)C23—H23B0.9700
S1—C81.729 (2)C24—C261.533 (5)
S1—C91.777 (2)C24—C251.534 (5)
N1—C71.313 (3)C24—H24A0.9800
N1—N21.402 (3)C25—H25A0.9700
N2—C81.307 (3)C25—H25B0.9700
N3—C81.354 (3)C26—C271.502 (12)
N3—C71.369 (3)C26—H26A0.9700
N3—N41.376 (3)C26—H26B0.9700
N4—C91.285 (3)C27—C281.536 (5)
C1—C21.388 (4)C27—C291.541 (5)
C1—C61.390 (3)C27—H270.9800
C1—C71.465 (3)C28—H28A0.9700
C2—C31.376 (4)C28—H28B0.9700
C3—C41.375 (4)C29—H29A0.9700
C3—H30.9300C29—H29B0.9700
C4—C51.372 (5)C31—C321.535 (5)
C4—H40.9300C31—H31A0.9700
C5—C61.376 (4)C31—H31B0.9700
C5—H50.9300C32—C391.527 (5)
C6—H60.9300C32—C331.528 (5)
C9—C101.506 (3)C32—H320.9800
C10—C181.506 (4)C33—C341.528 (5)
C10—C411.510 (4)C33—H33A0.9700
C10—C311.520 (5)C33—H33B0.9700
C10—C351.529 (5)C34—C361.530 (5)
C10—C111.536 (4)C34—C351.540 (5)
C10—C451.537 (4)C34—H340.9800
C10—C381.537 (5)C35—H35A0.9700
C10—C281.538 (4)C35—H35B0.9700
C10—C251.543 (4)C36—C371.447 (19)
C10—C211.549 (4)C36—H36A0.9700
C10—C481.553 (4)C36—H36B0.9700
C11—C121.531 (5)C37—C391.529 (5)
C11—H11A0.9700C37—C381.537 (5)
C11—H11B0.9700C37—H370.9800
C12—C191.532 (5)C38—H38A0.9700
C12—C131.533 (5)C38—H38B0.9700
C12—H12A0.9800C39—H39A0.9700
C13—C141.534 (5)C39—H39B0.9700
C13—H13A0.9700C41—C421.532 (5)
C13—H13B0.9700C41—H41A0.9700
C14—C161.533 (5)C41—H41B0.9700
C14—C151.538 (5)C42—C431.525 (5)
C14—H14A0.9800C42—C491.527 (5)
C15—H15A0.9700C42—H420.9800
C15—H15B0.9700C43—C441.533 (5)
C16—C171.500 (13)C43—H43A0.9700
C16—H16A0.9700C43—H43B0.9700
C16—H16B0.9700C44—C461.532 (5)
C17—C191.531 (5)C44—C451.537 (5)
C17—C181.532 (5)C44—H440.9800
C17—H17A0.9800C45—H45A0.9700
C18—H18A0.9700C45—H45B0.9700
C18—H18B0.9700C46—C471.531 (14)
C19—H19A0.9700C46—H46A0.9700
C19—H19B0.9700C46—H46B0.9700
C21—C221.531 (5)C47—C491.528 (5)
C21—H21A0.9700C47—C481.537 (5)
C21—H21B0.9700C47—H470.9800
C22—C231.527 (5)C48—H48A0.9700
C22—C291.529 (5)C48—H48B0.9700
C22—H220.9800C49—H49A0.9700
C23—C241.534 (5)C49—H49B0.9700
C23—H23A0.9700
C8—S1—C987.73 (11)C24—C25—H25B109.5
C7—N1—N2109.47 (19)C10—C25—H25B109.5
C8—N2—N1104.77 (19)H25A—C25—H25B108.1
C8—N3—C7105.86 (19)C27—C26—C24110.5 (7)
C8—N3—N4118.77 (18)C27—C26—H26A109.6
C7—N3—N4135.24 (19)C24—C26—H26A109.6
C9—N4—N3108.23 (19)C27—C26—H26B109.6
C2—C1—C6118.2 (2)C24—C26—H26B109.6
C2—C1—C7123.4 (2)H26A—C26—H26B108.1
C6—C1—C7118.4 (2)C26—C27—C28109.9 (7)
C3—C2—C1121.2 (3)C26—C27—C29108.2 (7)
C3—C2—Cl1118.5 (2)C28—C27—C29109.1 (7)
C1—C2—Cl1120.3 (2)C26—C27—H27109.9
C4—C3—C2119.5 (3)C28—C27—H27109.9
C4—C3—H3120.3C29—C27—H27109.9
C2—C3—H3120.3C27—C28—C10111.4 (5)
C5—C4—C3120.5 (3)C27—C28—H28A109.3
C5—C4—H4119.8C10—C28—H28A109.3
C3—C4—H4119.8C27—C28—H28B109.3
C4—C5—C6119.9 (3)C10—C28—H28B109.3
C4—C5—H5120.0H28A—C28—H28B108.0
C6—C5—H5120.0C22—C29—C27110.1 (5)
C5—C6—C1120.7 (3)C22—C29—H29A109.6
C5—C6—H6119.6C27—C29—H29A109.6
C1—C6—H6119.6C22—C29—H29B109.6
N1—C7—N3108.0 (2)C27—C29—H29B109.6
N1—C7—C1126.5 (2)H29A—C29—H29B108.2
N3—C7—C1125.3 (2)C10—C31—C32109.6 (5)
N2—C8—N3111.9 (2)C10—C31—H31A109.7
N2—C8—S1139.2 (2)C32—C31—H31A109.7
N3—C8—S1108.93 (17)C10—C31—H31B109.7
N4—C9—C10122.7 (2)C32—C31—H31B109.7
N4—C9—S1116.27 (17)H31A—C31—H31B108.2
C10—C9—S1121.00 (16)C39—C32—C33110.4 (10)
C9—C10—C18110.3 (3)C39—C32—C31105.3 (10)
C9—C10—C41107.4 (3)C33—C32—C31109.3 (6)
C9—C10—C31109.8 (4)C39—C32—H32110.5
C9—C10—C35109.7 (4)C33—C32—H32110.5
C31—C10—C35112.8 (5)C31—C32—H32110.5
C9—C10—C11110.5 (3)C32—C33—C34111.3 (6)
C18—C10—C11113.4 (4)C32—C33—H33A109.4
C9—C10—C45109.8 (3)C34—C33—H33A109.4
C41—C10—C45111.7 (4)C32—C33—H33B109.4
C9—C10—C38105.9 (5)C34—C33—H33B109.4
C31—C10—C38109.8 (5)H33A—C33—H33B108.0
C35—C10—C38108.7 (5)C33—C34—C36109.0 (10)
C9—C10—C28109.3 (3)C33—C34—C35108.0 (6)
C9—C10—C25110.5 (3)C36—C34—C35106.3 (10)
C28—C10—C25107.9 (4)C33—C34—H34111.1
C9—C10—C21113.2 (3)C36—C34—H34111.1
C28—C10—C21108.0 (4)C35—C34—H34111.1
C25—C10—C21107.8 (4)C10—C35—C34109.0 (5)
C9—C10—C48110.8 (3)C10—C35—H35A109.9
C41—C10—C48109.8 (4)C34—C35—H35A109.9
C45—C10—C48107.3 (4)C10—C35—H35B109.9
C12—C11—C10109.9 (4)C34—C35—H35B109.9
C12—C11—H11A109.7H35A—C35—H35B108.3
C10—C11—H11A109.7C37—C36—C34114.5 (11)
C12—C11—H11B109.7C37—C36—H36A108.6
C10—C11—H11B109.7C34—C36—H36A108.6
H11A—C11—H11B108.2C37—C36—H36B108.6
C11—C12—C19108.5 (7)C34—C36—H36B108.6
C11—C12—C13109.8 (5)H36A—C36—H36B107.6
C19—C12—C13108.3 (7)C36—C37—C39109.1 (11)
C11—C12—H12A110.1C36—C37—C38108.6 (11)
C19—C12—H12A110.1C39—C37—C38109.7 (11)
C13—C12—H12A110.1C36—C37—H37109.8
C12—C13—C14110.9 (5)C39—C37—H37109.8
C12—C13—H13A109.5C38—C37—H37109.8
C14—C13—H13A109.5C10—C38—C37107.1 (7)
C12—C13—H13B109.5C10—C38—H38A110.3
C14—C13—H13B109.5C37—C38—H38A110.3
H13A—C13—H13B108.0C10—C38—H38B110.3
C16—C14—C13109.7 (7)C37—C38—H38B110.3
C16—C14—C15106.7 (7)H38A—C38—H38B108.6
C13—C14—C15108.6 (5)C32—C39—C37111.3 (7)
C16—C14—H14A110.6C32—C39—H39A109.4
C13—C14—H14A110.6C37—C39—H39A109.4
C15—C14—H14A110.6C32—C39—H39B109.4
C14—C15—C10110.2 (4)C37—C39—H39B109.4
C14—C15—H15A109.6H39A—C39—H39B108.0
C10—C15—H15A109.6C10—C41—C42109.0 (4)
C14—C15—H15B109.6C10—C41—H41A109.9
C10—C15—H15B109.6C42—C41—H41A109.9
H15A—C15—H15B108.1C10—C41—H41B109.9
C17—C16—C14111.0 (7)C42—C41—H41B109.9
C17—C16—H16A109.4H41A—C41—H41B108.3
C14—C16—H16A109.4C43—C42—C49108.2 (7)
C17—C16—H16B109.4C43—C42—C41109.5 (5)
C14—C16—H16B109.4C49—C42—C41109.2 (7)
H16A—C16—H16B108.0C43—C42—H42110.0
C16—C17—C19112.3 (7)C49—C42—H42110.0
C16—C17—C18107.1 (8)C41—C42—H42110.0
C19—C17—C18109.9 (7)C42—C43—C44110.6 (5)
C16—C17—H17A109.2C42—C43—H43A109.5
C19—C17—H17A109.2C44—C43—H43A109.5
C18—C17—H17A109.2C42—C43—H43B109.5
C10—C18—C17108.7 (5)C44—C43—H43B109.5
C10—C18—H18A109.9H43A—C43—H43B108.1
C17—C18—H18A109.9C46—C44—C43110.1 (7)
C10—C18—H18B109.9C46—C44—C45109.4 (7)
C17—C18—H18B109.9C43—C44—C45108.6 (5)
H18A—C18—H18B108.3C46—C44—H44109.6
C17—C19—C12110.2 (5)C43—C44—H44109.6
C17—C19—H19A109.6C45—C44—H44109.6
C12—C19—H19A109.6C44—C45—C10109.3 (4)
C17—C19—H19B109.6C44—C45—H45A109.8
C12—C19—H19B109.6C10—C45—H45A109.8
H19A—C19—H19B108.1C44—C45—H45B109.8
C22—C21—C10111.3 (4)C10—C45—H45B109.8
C22—C21—H21A109.4H45A—C45—H45B108.3
C10—C21—H21A109.4C47—C46—C44109.9 (7)
C22—C21—H21B109.4C47—C46—H46A109.7
C10—C21—H21B109.4C44—C46—H46A109.7
H21A—C21—H21B108.0C47—C46—H46B109.7
C23—C22—C29109.8 (7)C44—C46—H46B109.7
C23—C22—C21110.5 (5)H46A—C46—H46B108.2
C29—C22—C21107.7 (7)C49—C47—C46108.7 (7)
C23—C22—H22109.6C49—C47—C48107.1 (8)
C29—C22—H22109.6C46—C47—C48109.1 (8)
C21—C22—H22109.6C49—C47—H47110.6
C22—C23—C24109.1 (5)C46—C47—H47110.6
C22—C23—H23A109.9C48—C47—H47110.6
C24—C23—H23A109.9C47—C48—C10110.6 (5)
C22—C23—H23B109.9C47—C48—H48A109.5
C24—C23—H23B109.9C10—C48—H48A109.5
H23A—C23—H23B108.3C47—C48—H48B109.5
C26—C24—C25111.2 (7)C10—C48—H48B109.5
C26—C24—C23108.1 (7)H48A—C48—H48B108.1
C25—C24—C23109.0 (5)C42—C49—C47112.4 (6)
C26—C24—H24A109.5C42—C49—H49A109.1
C25—C24—H24A109.5C47—C49—H49A109.1
C23—C24—H24A109.5C42—C49—H49B109.1
C24—C25—C10110.7 (4)C47—C49—H49B109.1
C24—C25—H25A109.5H49A—C49—H49B107.9
C10—C25—H25A109.5
C7—N1—N2—C8−0.4 (3)C31—C10—C25—C24−80.5 (6)
C8—N3—N4—C92.4 (3)C35—C10—C25—C2477.4 (7)
C7—N3—N4—C9177.5 (2)C11—C10—C25—C24−72.9 (6)
C6—C1—C2—C31.3 (4)C45—C10—C25—C2466.5 (6)
C7—C1—C2—C3−177.9 (3)C38—C10—C25—C249.1 (12)
C6—C1—C2—Cl1−177.2 (2)C28—C10—C25—C2457.3 (6)
C7—C1—C2—Cl13.6 (4)C21—C10—C25—C24−59.1 (6)
C1—C2—C3—C4−0.1 (5)C48—C10—C25—C24−43.5 (8)
Cl1—C2—C3—C4178.4 (3)C25—C24—C26—C2756.9 (9)
C2—C3—C4—C5−1.1 (5)C23—C24—C26—C27−62.7 (9)
C3—C4—C5—C61.1 (5)C24—C26—C27—C28−57.4 (9)
C4—C5—C6—C10.1 (5)C24—C26—C27—C2961.6 (9)
C2—C1—C6—C5−1.3 (4)C26—C27—C28—C1060.1 (9)
C7—C1—C6—C5177.9 (2)C29—C27—C28—C10−58.4 (9)
N2—N1—C7—N30.5 (3)C9—C10—C28—C27−179.2 (6)
N2—N1—C7—C1−175.0 (2)C18—C10—C28—C2784.3 (15)
C8—N3—C7—N1−0.3 (3)C41—C10—C28—C27−44.3 (9)
N4—N3—C7—N1−175.9 (2)C31—C10—C28—C2712.3 (12)
C8—N3—C7—C1175.2 (2)C35—C10—C28—C27−77.2 (7)
N4—N3—C7—C1−0.3 (4)C11—C10—C28—C2740.8 (9)
C2—C1—C7—N1−129.4 (3)C45—C10—C28—C27−83.9 (12)
C6—C1—C7—N151.5 (4)C38—C10—C28—C2785.6 (9)
C2—C1—C7—N355.9 (4)C25—C10—C28—C27−59.0 (7)
C6—C1—C7—N3−123.3 (3)C21—C10—C28—C2757.3 (7)
N1—N2—C8—N30.2 (3)C48—C10—C28—C2769.6 (7)
N1—N2—C8—S1179.3 (2)C23—C22—C29—C2758.9 (9)
C7—N3—C8—N20.1 (3)C21—C22—C29—C27−61.5 (9)
N4—N3—C8—N2176.5 (2)C26—C27—C29—C22−59.3 (9)
C7—N3—C8—S1−179.28 (15)C28—C27—C29—C2260.2 (9)
N4—N3—C8—S1−2.9 (3)C9—C10—C31—C32179.2 (6)
C9—S1—C8—N2−177.2 (3)C18—C10—C31—C32−38.4 (10)
C9—S1—C8—N31.85 (18)C41—C10—C31—C3285.4 (8)
N3—N4—C9—C10179.52 (19)C35—C10—C31—C3256.6 (9)
N3—N4—C9—S1−0.7 (3)C11—C10—C31—C32−84.8 (14)
C8—S1—C9—N4−0.7 (2)C45—C10—C31—C3221.6 (12)
C8—S1—C9—C10179.10 (19)C38—C10—C31—C32−64.7 (9)
N4—C9—C10—C1887.7 (5)C28—C10—C31—C32−12.4 (13)
S1—C9—C10—C18−92.1 (5)C25—C10—C31—C3275.3 (7)
N4—C9—C10—C41−79.5 (5)C21—C10—C31—C32−76.9 (8)
S1—C9—C10—C41100.7 (4)C48—C10—C31—C32−74.5 (8)
N4—C9—C10—C31−122.0 (6)C10—C31—C32—C3962.7 (10)
S1—C9—C10—C3158.3 (6)C10—C31—C32—C33−56.0 (10)
N4—C9—C10—C352.5 (6)C39—C32—C33—C34−55.0 (11)
S1—C9—C10—C35−177.3 (6)C31—C32—C33—C3460.4 (11)
N4—C9—C10—C11−146.2 (5)C32—C33—C34—C3653.4 (12)
S1—C9—C10—C1134.0 (5)C32—C33—C34—C35−61.7 (11)
N4—C9—C10—C4542.2 (5)C9—C10—C35—C34179.0 (6)
S1—C9—C10—C45−137.6 (4)C18—C10—C35—C3471.2 (8)
N4—C9—C10—C38119.5 (6)C41—C10—C35—C34−76.9 (7)
S1—C9—C10—C38−60.2 (6)C31—C10—C35—C34−58.3 (9)
N4—C9—C10—C2865.9 (5)C11—C10—C35—C34−40.1 (11)
S1—C9—C10—C28−113.9 (5)C45—C10—C35—C3481.9 (10)
N4—C9—C10—C25−52.7 (5)C38—C10—C35—C3463.7 (9)
S1—C9—C10—C25127.5 (4)C28—C10—C35—C3477.7 (8)
N4—C9—C10—C21−173.8 (5)C25—C10—C35—C34−80.0 (7)
S1—C9—C10—C216.5 (5)C21—C10—C35—C34−6.1 (12)
N4—C9—C10—C48160.6 (5)C48—C10—C35—C3428.1 (11)
S1—C9—C10—C48−19.2 (5)C33—C34—C35—C1058.8 (10)
C9—C10—C11—C12178.9 (5)C36—C34—C35—C10−58.1 (11)
C18—C10—C11—C12−56.8 (7)C33—C34—C36—C37−57.0 (15)
C41—C10—C11—C1279.3 (6)C35—C34—C36—C3759.2 (15)
C31—C10—C11—C1286.4 (12)C34—C36—C37—C3958.3 (16)
C35—C10—C11—C1238.2 (9)C34—C36—C37—C38−61.3 (15)
C45—C10—C11—C12−13.2 (10)C9—C10—C38—C37178.9 (8)
C38—C10—C11—C12−74.8 (7)C18—C10—C38—C37−77.9 (12)
C28—C10—C11—C12−41.5 (8)C41—C10—C38—C3729.2 (14)
C25—C10—C11—C1268.4 (6)C31—C10—C38—C3760.5 (10)
C21—C10—C11—C12−79.9 (9)C35—C10—C38—C37−63.3 (10)
C48—C10—C11—C12−80.7 (7)C11—C10—C38—C3768.1 (9)
C10—C11—C12—C1956.9 (7)C45—C10—C38—C37−74.7 (9)
C10—C11—C12—C13−61.3 (8)C28—C10—C38—C37−78.8 (9)
C11—C12—C13—C1458.0 (8)C25—C10—C38—C37−13.2 (15)
C19—C12—C13—C14−60.4 (8)C21—C10—C38—C3770.6 (9)
C12—C13—C14—C1658.8 (8)C48—C10—C38—C3775.3 (10)
C12—C13—C14—C15−57.4 (8)C36—C37—C38—C1060.9 (11)
C16—C14—C15—C10−57.6 (8)C39—C37—C38—C10−58.3 (11)
C13—C14—C15—C1060.6 (7)C33—C32—C39—C3756.3 (15)
C9—C10—C15—C14178.8 (5)C31—C32—C39—C37−61.6 (15)
C18—C10—C15—C1459.4 (6)C36—C37—C39—C32−57.2 (17)
C41—C10—C15—C14−83.6 (6)C38—C37—C39—C3261.6 (15)
C31—C10—C15—C14−71.9 (6)C9—C10—C41—C42179.3 (5)
C35—C10—C15—C1479.6 (9)C18—C10—C41—C4218.2 (10)
C11—C10—C15—C14−62.9 (6)C31—C10—C41—C42−80.4 (8)
C45—C10—C15—C1473.9 (6)C35—C10—C41—C4272.4 (6)
C38—C10—C15—C1441.7 (9)C11—C10—C41—C42−76.2 (6)
C28—C10—C15—C1468.5 (6)C45—C10—C41—C4258.8 (7)
C25—C10—C15—C14−79.6 (11)C38—C10—C41—C42−31.2 (11)
C21—C10—C15—C14−44.0 (8)C28—C10—C41—C4243.7 (8)
C48—C10—C15—C14−17.8 (10)C25—C10—C41—C4277.9 (9)
C13—C14—C16—C17−55.4 (9)C21—C10—C41—C42−67.3 (6)
C15—C14—C16—C1762.1 (9)C48—C10—C41—C42−60.2 (7)
C14—C16—C17—C1955.4 (10)C10—C41—C42—C43−58.9 (8)
C14—C16—C17—C18−65.3 (9)C10—C41—C42—C4959.4 (7)
C9—C10—C18—C17−179.2 (5)C49—C42—C43—C44−58.1 (8)
C41—C10—C18—C17−18.5 (11)C41—C42—C43—C4460.9 (8)
C31—C10—C18—C1738.6 (10)C42—C43—C44—C4659.5 (9)
C35—C10—C18—C17−72.1 (7)C42—C43—C44—C45−60.2 (8)
C11—C10—C18—C1756.4 (7)C46—C44—C45—C10−62.2 (8)
C45—C10—C18—C17−81.6 (7)C43—C44—C45—C1057.9 (8)
C38—C10—C18—C1793.9 (12)C9—C10—C45—C44−177.9 (5)
C28—C10—C18—C17−88.2 (14)C18—C10—C45—C4483.3 (8)
C25—C10—C18—C17−45.1 (8)C41—C10—C45—C44−58.9 (7)
C21—C10—C18—C1766.2 (7)C31—C10—C45—C44−20.3 (11)
C48—C10—C18—C1775.9 (7)C35—C10—C45—C44−81.2 (8)
C16—C17—C18—C1064.3 (8)C11—C10—C45—C4414.1 (10)
C19—C17—C18—C10−57.9 (9)C38—C10—C45—C4480.9 (7)
C16—C17—C19—C12−57.3 (10)C28—C10—C45—C4489.4 (13)
C18—C17—C19—C1261.8 (9)C25—C10—C45—C44−67.0 (6)
C11—C12—C19—C17−60.7 (9)C21—C10—C45—C4443.0 (8)
C13—C12—C19—C1758.4 (9)C48—C10—C45—C4461.5 (7)
C9—C10—C21—C22179.6 (5)C43—C44—C46—C47−59.0 (10)
C18—C10—C21—C22−68.5 (6)C45—C44—C46—C4760.2 (10)
C41—C10—C21—C2271.9 (6)C44—C46—C47—C4957.9 (10)
C31—C10—C21—C2283.3 (7)C44—C46—C47—C48−58.5 (10)
C35—C10—C21—C224.8 (11)C49—C47—C48—C10−57.9 (9)
C11—C10—C21—C2290.3 (9)C46—C47—C48—C1059.5 (9)
C45—C10—C21—C22−42.5 (8)C9—C10—C48—C47179.3 (6)
C38—C10—C21—C22−83.9 (8)C18—C10—C48—C47−76.5 (7)
C28—C10—C21—C22−59.3 (7)C41—C10—C48—C4760.9 (8)
C25—C10—C21—C2257.0 (7)C31—C10—C48—C4774.5 (7)
C48—C10—C21—C22−91.2 (12)C35—C10—C48—C47−29.9 (11)
C10—C21—C22—C23−58.2 (8)C11—C10—C48—C4779.7 (8)
C10—C21—C22—C2961.7 (8)C45—C10—C48—C47−60.8 (8)
C29—C22—C23—C24−59.5 (7)C38—C10—C48—C47−90.9 (10)
C21—C22—C23—C2459.1 (8)C28—C10—C48—C47−71.0 (7)
C22—C23—C24—C2660.4 (8)C25—C10—C48—C4739.6 (9)
C22—C23—C24—C25−60.6 (8)C21—C10—C48—C4778.9 (12)
C26—C24—C25—C10−57.2 (8)C43—C42—C49—C4759.0 (10)
C23—C24—C25—C1061.9 (8)C41—C42—C49—C47−60.1 (10)
C9—C10—C25—C24176.7 (5)C46—C47—C49—C42−59.2 (11)
C18—C10—C25—C2442.7 (8)C48—C47—C49—C4258.6 (10)
C41—C10—C25—C24−95.8 (9)
Acknowledgements top

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer and for technical support, respectively.

references
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