PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2494–o2495.
Published online 2010 September 4. doi:  10.1107/S1600536810034951
PMCID: PMC2983261

4-(3-Fluoro­phen­yl)-1-(2-oxoindolin-3-yl­idene)thio­semicarbazide

Abstract

In the title compound, C15H11FN4OS, there are three independent mol­ecules, each with a disordered 3-fluoro­phenyl group [occupancy ratios = 0.547 (17):0.453 (17), 0.645 (5):0.355 (5) and 0.626 (15):0.374 (15)] and displaying dihedral angles of 4.2 (3), 25.2 (6) and 32.4 (5)° between the 2-oxoindoline and fluoro-substituted phenyl rings. Strong intra­molecular N—H(...)N and N—H(...)O and weak intra­molecular C—H(...)S hydrogen bonds complete S(5) and S(6) ring motifs, while strong inter­molecular N—H(...)O hydrogen bonds inter­connect the three independent mol­ecules through R 3 3(12) ring motifs. The three-mol­ecule units are in turn linked into polymeric sheets via C—H(...)F and C—H(...)S hydrogen bonds and π–π inter­actions [centroid–centroid distances in the range 3.520 (2)–3.820 (9) Å].

Related literature

For our work on the synthesis of biologically important isatin (systematic name 1H-indole-2,3-dione) derivatives, see: Pervez et al. (2007 [triangle], 2008 [triangle], 2009 [triangle]). For related structures, see: Pervez et al. (2010 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2494-scheme1.jpg

Experimental

Crystal data

  • C15H11FN4OS
  • M r = 314.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2494-efi2.jpg
  • a = 8.0582 (3) Å
  • b = 14.3640 (5) Å
  • c = 19.4456 (8) Å
  • α = 86.338 (2)°
  • β = 89.299 (1)°
  • γ = 75.128 (2)°
  • V = 2170.93 (14) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 296 K
  • 0.28 × 0.22 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.942, T max = 0.950
  • 31845 measured reflections
  • 7851 independent reflections
  • 4225 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.178
  • S = 1.02
  • 7851 reflections
  • 573 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034951/bg2363sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034951/bg2363Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HP, MY and MR thank the Ministry of Science & Technology (MoST), Government of Pakistan, for partial financial assistance under Projects for the Strengthening of S & T Education in Universities (project No. P&D/S&T/2001/231).

supplementary crystallographic information

Comment

In continuation of our work on the synthesis of biologically important isatin derivatives (Pervez et al., 2007, 2008, 2009), we report herein the structure and preparation of the title compound (I, Fig. 1). When compared with the crystal structure of i.e. 4-(2-fluorophenyl)-1-(2-oxoindolin-3-ylidene) thiosemicarbazide (II) (Pervez et al., 2010), it can be noticed they differ in the position of the fluoro function at the phenyl ring bound to N4 in the thiosemicarbazone moiety.

There are three independent molecules in (I). The 3-fluorophenyl moiety is disordered in each one with different site occupancy ratios (0.547 (17):0.453 (17), 0.645 (5):0.355 (5) and 0.626 (15):0.374 (15), respectively. In all three molecules, the 2-oxoindolin A (C1–C8/N1/O1), B (C16–C23/N5/O2) and C (C31–C38/N9/O3) groups are planar with r. m. s. deviations of 0.0054, 0.0100 and 0.0036 Å, respectively. The thiosemicarbazide D (N2/N3/C9/S1/N4), E (N6/N7/C24/S2/N8) and F (N10/N11/C39/S3/N12) groups, in turn, are also planar with r. m. s. deviations of 0.0060, 0.0336 and 0.0192 Å, respectively. The dihedral angles between A/D, B/E, C/F are 9.24 (15), 7.67 (14), 6.13 (17).

Due to strong intramolecular H-bondings of N—H···N and N—H···O type, there exist one S(5) and one S(6) (Bernstein et al., 1995) ring motif, respectively (Table 1, Fig. 2). A weak intramolecular C—H···S H-bond is also present in each molecule (Table 1). The three molecules are interconnected through strong intermolecular H-bonds of N—H···O type (Table 1, Fig. 2) and complete R33(12) ring motifs. The molecules are stabilized in the form of polymeric sheets which are finally formed due to C—H···F and C—H···S interactions (Table 1, Fig. 2). In the stabilization of molecules, π–π interactions present play a relevant role.

Experimental

To a hot solution of isatin (0.74 g, 5.0 mmol) in ethanol (10 ml) containing a few drops of glacial acetic acid was added 4-(3-fluorophenyl)thiosemicarbazide (0.93 g, 5.0 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then heated under reflux for 2 h. The yellow crystalline solid formed during heating was collected by suction filtration. Thorough washing with hot ethanol followed by ether afforded the target compound (I) in pure form (1.12 g, 71%), m. p. 513 K (d). The single crystals of (I) were grown in acetone-ethanol (1:4) by diffusion method at room temperature.

Refinement

The 3-fluorophenyl moiety is disordered in all three independent structures and their phenyl rings have been fitted into regular hexagons (C···C = 1.39Å.). The occupancy ratio of disordered groups is 0.547 (17):0.453 (17), 0.645 (5):0.355 (5) and 0.626 (15):0.374 (15), respectively.

The H-atoms were positioned geometrically (N—H = 0.86, C–H = 0.93 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.2 for all H-atoms.

Figures

Fig. 1.
View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
Fig. 2.
The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric sheets with central R33(12) ring motifs. The H-atoms not involved in H-bondings have been omitted for clarity.

Crystal data

C15H11FN4OSZ = 6
Mr = 314.34F(000) = 972
Triclinic, P1Dx = 1.443 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0582 (3) ÅCell parameters from 4225 reflections
b = 14.3640 (5) Åθ = 2.1–25.3°
c = 19.4456 (8) ŵ = 0.24 mm1
α = 86.338 (2)°T = 296 K
β = 89.299 (1)°Prisms, yellow
γ = 75.128 (2)°0.28 × 0.22 × 0.20 mm
V = 2170.93 (14) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer7851 independent reflections
Radiation source: fine-focus sealed tube4225 reflections with I > 2σ(I)
graphiteRint = 0.059
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 2.1°
ω scansh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −16→17
Tmin = 0.942, Tmax = 0.950l = −23→23
31845 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.178w = 1/[σ2(Fo2) + (0.0739P)2 + 0.9447P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7851 reflectionsΔρmax = 0.31 e Å3
573 parametersΔρmin = −0.30 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0055 (13)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/UeqOcc. (<1)
S10.26523 (19)0.98975 (8)0.34158 (6)0.0868 (5)
F1A0.286 (9)1.302 (7)0.217 (8)0.109 (6)0.547 (17)
O10.1679 (4)0.68968 (18)0.35500 (15)0.0677 (11)
N10.0699 (4)0.5919 (2)0.28535 (17)0.0604 (11)
N20.1031 (4)0.8231 (2)0.22575 (16)0.0538 (11)
N30.1585 (4)0.8620 (2)0.27979 (16)0.0576 (11)
N40.1882 (4)0.9854 (2)0.20740 (16)0.0596 (11)
C10.1113 (5)0.6730 (3)0.3007 (2)0.0543 (16)
C20.0125 (5)0.5970 (3)0.2173 (2)0.0567 (16)
C3−0.0410 (5)0.5294 (3)0.1832 (3)0.0733 (19)
C4−0.0925 (6)0.5520 (3)0.1160 (3)0.086 (2)
C5−0.0896 (6)0.6393 (3)0.0833 (3)0.0860 (19)
C6−0.0350 (5)0.7081 (3)0.1178 (2)0.0703 (16)
C70.0155 (5)0.6861 (3)0.1854 (2)0.0524 (14)
C80.0788 (4)0.7381 (2)0.23583 (19)0.0501 (12)
C90.2032 (5)0.9476 (2)0.27259 (19)0.0532 (16)
C10A0.2262 (19)1.0704 (11)0.1760 (10)0.0534 (18)0.547 (17)
C11A0.246 (2)1.0776 (12)0.1049 (10)0.061 (4)0.547 (17)
C12A0.263 (2)1.1637 (14)0.0722 (9)0.103 (4)0.547 (17)
C13A0.2589 (19)1.2426 (11)0.1105 (10)0.095 (3)0.547 (17)
C14A0.2389 (18)1.2354 (11)0.1816 (10)0.047 (4)0.547 (17)
C15A0.2225 (18)1.1493 (13)0.2143 (9)0.047 (3)0.547 (17)
C13B0.272 (2)1.2310 (14)0.1052 (13)0.095 (3)0.453 (17)
C14B0.3003 (18)1.2194 (13)0.1760 (13)0.047 (4)0.453 (17)
C15B0.267 (2)1.1406 (16)0.2134 (11)0.047 (3)0.453 (17)
C11B0.178 (2)1.0849 (16)0.1092 (13)0.061 (4)0.453 (17)
F1B0.285 (11)1.299 (9)0.212 (10)0.109 (6)0.453 (17)
C10B0.206 (2)1.0733 (14)0.1800 (13)0.0534 (18)0.453 (17)
C12B0.211 (3)1.1638 (19)0.0718 (11)0.103 (4)0.453 (17)
S20.57526 (16)0.71997 (8)0.27758 (6)0.0787 (5)
F2A0.2702 (6)0.4925 (3)0.0210 (2)0.141 (2)0.645 (5)
O20.7099 (3)0.51552 (17)0.47192 (12)0.0573 (10)
N50.6913 (4)0.3622 (2)0.50827 (15)0.0536 (11)
N60.5561 (4)0.4643 (2)0.34248 (16)0.0518 (11)
N70.5872 (4)0.5516 (2)0.33703 (16)0.0582 (11)
N80.5036 (4)0.5648 (2)0.22516 (16)0.0603 (11)
C160.6704 (4)0.4392 (3)0.46365 (19)0.0476 (12)
C170.6293 (4)0.2887 (3)0.48129 (19)0.0496 (14)
C180.6306 (5)0.1991 (3)0.5113 (2)0.0643 (17)
C190.5656 (6)0.1399 (3)0.4723 (3)0.0753 (19)
C200.5044 (5)0.1674 (3)0.4063 (3)0.0730 (19)
C210.5038 (5)0.2575 (3)0.3766 (2)0.0590 (16)
C220.5672 (4)0.3181 (3)0.41468 (19)0.0480 (12)
C230.5922 (4)0.4138 (2)0.40045 (18)0.0448 (12)
C240.5525 (5)0.6092 (3)0.2761 (2)0.0546 (14)
C25A0.4523 (6)0.5959 (3)0.15770 (19)0.0605 (17)0.645 (5)
C26A0.3903 (5)0.5317 (3)0.12122 (16)0.0715 (17)0.645 (5)
C27A0.3384 (4)0.5553 (3)0.05302 (16)0.093 (2)0.645 (5)
C28A0.3485 (7)0.6432 (3)0.0213 (2)0.113 (3)0.645 (5)
C29A0.4105 (9)0.7074 (3)0.0578 (3)0.112 (3)0.645 (5)
C30A0.4624 (7)0.6837 (3)0.1260 (3)0.087 (2)0.645 (5)
C28B0.3502 (8)0.64587 (14)0.0212 (2)0.113 (3)0.355 (5)
C29B0.4134 (9)0.70940 (11)0.0579 (2)0.112 (3)0.355 (5)
C30B0.4662 (8)0.68490 (10)0.1259 (2)0.087 (2)0.355 (5)
C26B0.3926 (4)0.53333 (17)0.12057 (16)0.0715 (17)0.355 (5)
F2B0.4266 (11)0.79699 (12)0.0362 (3)0.141 (2)0.355 (5)
C25B0.4558 (5)0.59686 (14)0.15726 (19)0.0605 (17)0.355 (5)
C27B0.3398 (5)0.55784 (16)0.05254 (18)0.093 (2)0.355 (5)
S30.73951 (16)0.32405 (7)0.17558 (5)0.0755 (5)
F3A0.683 (2)0.0464 (13)0.0360 (7)0.164 (6)0.626 (15)
O31.0173 (2)0.42029 (11)0.35189 (7)0.0627 (10)
N91.1234 (3)0.36096 (15)0.46050 (8)0.0523 (11)
N100.9445 (4)0.2242 (2)0.35231 (15)0.0479 (11)
N110.8890 (4)0.2813 (2)0.29489 (15)0.0504 (11)
N120.8135 (4)0.1556 (2)0.25218 (15)0.0553 (11)
C311.0500 (4)0.3568 (3)0.3997 (2)0.0491 (12)
C321.1409 (4)0.2743 (3)0.50170 (19)0.0474 (12)
C331.2072 (5)0.2516 (3)0.5665 (2)0.0618 (17)
C341.2097 (6)0.1617 (3)0.5956 (2)0.0728 (17)
C351.1458 (6)0.0964 (3)0.5617 (2)0.0702 (16)
C361.0786 (5)0.1204 (3)0.4960 (2)0.0585 (16)
C371.0759 (4)0.2105 (2)0.46541 (18)0.0451 (12)
C381.0161 (4)0.2592 (2)0.39974 (18)0.0443 (12)
C390.8147 (4)0.2479 (3)0.24190 (18)0.0495 (12)
C40A0.7514 (15)0.0966 (8)0.2117 (7)0.0510 (19)0.626 (15)
C41A0.6868 (14)0.0235 (9)0.2428 (6)0.051 (3)0.626 (15)
C42A0.6494 (15)−0.0458 (8)0.2032 (8)0.087 (3)0.626 (15)
C43A0.6766 (16)−0.0420 (10)0.1324 (8)0.096 (3)0.626 (15)
C44A0.7412 (16)0.0311 (12)0.1013 (6)0.080 (4)0.626 (15)
C45A0.7786 (16)0.1004 (9)0.1409 (7)0.079 (4)0.626 (15)
C43B0.641 (3)−0.0376 (18)0.1348 (14)0.096 (3)0.374 (15)
C44B0.664 (3)0.047 (2)0.1009 (11)0.080 (4)0.374 (15)
C45B0.729 (3)0.1105 (16)0.1364 (13)0.079 (4)0.374 (15)
C41B0.749 (2)0.0064 (15)0.2397 (10)0.051 (3)0.374 (15)
F3B0.782 (4)0.046 (2)0.0301 (12)0.164 (6)0.374 (15)
C40B0.771 (3)0.0904 (15)0.2058 (13)0.0510 (19)0.374 (15)
C42B0.684 (3)−0.0576 (14)0.2042 (14)0.087 (3)0.374 (15)
H4−0.130290.507380.091890.1033*
H12A0.275931.168480.024600.1229*0.547 (17)
H13A0.269821.300180.088630.1141*0.547 (17)
H15A0.209141.144530.261890.0564*0.547 (17)
H4A0.148320.952570.179290.0714*
H5−0.124560.652520.037510.1029*
H6−0.032790.767120.095720.0840*
H11A0.248641.024810.079220.0737*0.547 (17)
H10.077710.542710.313940.0724*
H3−0.042210.469960.204890.0877*
H3A0.165720.832000.319790.0690*
H11B0.136501.039890.086910.0737*0.453 (17)
H12B0.192391.171510.024460.1229*0.453 (17)
H13B0.294831.283760.080150.1141*0.453 (17)
H15B0.285491.132790.260750.0564*0.453 (17)
H180.673190.179590.555530.0771*
H28A0.313810.65903−0.024330.1356*0.645 (5)
H29A0.417310.766180.036550.1343*0.645 (5)
H30A0.503900.726700.150380.1040*0.645 (5)
H190.562800.079150.491230.0901*
H200.462990.124870.381460.0875*
H210.461790.276470.332200.0708*
H26A0.383500.472890.142440.0855*0.645 (5)
H5A0.737010.358050.548460.0642*
H70.629140.572340.371670.0700*
H80.503670.505800.235870.0725*
H26B0.385600.474430.141530.0855*0.355 (5)
H27B0.297470.515330.027990.1120*0.355 (5)
H28B0.314840.66227−0.024300.1356*0.355 (5)
H30B0.508500.727410.150480.1040*0.355 (5)
H331.249100.295240.590020.0740*
H42A0.60619−0.094740.224000.1041*0.626 (15)
H43A0.65156−0.088330.105940.1151*0.626 (15)
H45A0.821820.149340.120090.0948*0.626 (15)
H341.255900.144010.639540.0870*
H351.147920.036360.583190.0843*
H361.036060.076800.472700.0701*
H41A0.668640.020900.290110.0610*0.626 (15)
H91.155740.410030.472850.0628*
H11C0.900530.339350.291570.0602*
H12C0.859040.128120.290470.0662*
H41B0.77744−0.007070.286100.0610*0.374 (15)
H42B0.66883−0.113830.226890.1041*0.374 (15)
H43B0.59776−0.080340.111080.1151*0.374 (15)
H45B0.743900.166670.113690.0948*0.374 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.1630 (13)0.0644 (7)0.0472 (7)−0.0563 (8)−0.0142 (7)0.0052 (5)
F1A0.171 (3)0.073 (6)0.098 (18)−0.060 (3)−0.026 (4)0.009 (3)
O10.095 (2)0.0627 (17)0.0505 (18)−0.0313 (15)−0.0056 (16)0.0048 (14)
N10.079 (2)0.0498 (18)0.056 (2)−0.0262 (16)−0.0075 (18)0.0103 (15)
N20.063 (2)0.0453 (18)0.052 (2)−0.0125 (15)−0.0083 (16)0.0004 (15)
N30.087 (2)0.0456 (17)0.043 (2)−0.0233 (16)−0.0071 (17)0.0037 (14)
N40.081 (2)0.0515 (18)0.049 (2)−0.0227 (16)−0.0092 (17)0.0012 (15)
C10.065 (3)0.048 (2)0.050 (3)−0.0154 (19)−0.001 (2)−0.0001 (19)
C20.058 (3)0.051 (2)0.065 (3)−0.0217 (18)−0.004 (2)−0.0005 (19)
C30.085 (3)0.061 (3)0.081 (4)−0.033 (2)−0.013 (3)0.003 (2)
C40.101 (4)0.078 (3)0.092 (4)−0.044 (3)−0.028 (3)−0.008 (3)
C50.106 (4)0.084 (3)0.073 (3)−0.034 (3)−0.036 (3)0.004 (3)
C60.083 (3)0.057 (2)0.072 (3)−0.021 (2)−0.020 (3)0.003 (2)
C70.053 (2)0.051 (2)0.052 (3)−0.0123 (18)−0.0080 (19)0.0025 (18)
C80.058 (2)0.040 (2)0.052 (2)−0.0130 (17)−0.0042 (19)0.0025 (17)
C90.072 (3)0.039 (2)0.048 (3)−0.0150 (18)−0.001 (2)0.0048 (17)
C10A0.060 (4)0.057 (2)0.043 (3)−0.016 (2)0.001 (3)0.003 (2)
C11A0.064 (11)0.070 (4)0.054 (4)−0.026 (8)0.007 (8)0.002 (3)
C12A0.166 (11)0.101 (4)0.057 (3)−0.070 (7)−0.007 (5)0.021 (3)
C13A0.143 (5)0.080 (4)0.069 (5)−0.049 (4)−0.011 (4)0.025 (4)
C14A0.017 (8)0.042 (5)0.073 (5)0.007 (6)0.001 (7)0.000 (4)
C15A0.036 (7)0.051 (4)0.050 (3)−0.005 (5)−0.004 (4)0.004 (2)
C13B0.143 (5)0.080 (4)0.069 (5)−0.049 (4)−0.011 (4)0.025 (4)
C14B0.017 (8)0.042 (5)0.073 (5)0.007 (6)0.001 (7)0.000 (4)
C15B0.036 (7)0.051 (4)0.050 (3)−0.005 (5)−0.004 (4)0.004 (2)
C11B0.064 (11)0.070 (4)0.054 (4)−0.026 (8)0.007 (8)0.002 (3)
F1B0.171 (3)0.073 (6)0.098 (18)−0.060 (3)−0.026 (4)0.009 (3)
C10B0.060 (4)0.057 (2)0.043 (3)−0.016 (2)0.001 (3)0.003 (2)
C12B0.166 (11)0.101 (4)0.057 (3)−0.070 (7)−0.007 (5)0.021 (3)
S20.1054 (9)0.0536 (6)0.0806 (9)−0.0286 (6)−0.0264 (7)0.0083 (5)
F2A0.187 (5)0.156 (4)0.081 (3)−0.042 (4)−0.040 (3)−0.010 (3)
O20.0734 (18)0.0495 (15)0.0530 (17)−0.0211 (13)−0.0128 (13)−0.0081 (12)
N50.065 (2)0.0560 (19)0.0413 (19)−0.0184 (16)−0.0111 (16)−0.0009 (15)
N60.059 (2)0.0531 (18)0.046 (2)−0.0181 (15)−0.0037 (16)−0.0072 (15)
N70.081 (2)0.0503 (18)0.047 (2)−0.0237 (16)−0.0203 (17)0.0018 (15)
N80.083 (2)0.0583 (19)0.043 (2)−0.0247 (17)−0.0149 (17)0.0008 (16)
C160.046 (2)0.049 (2)0.047 (2)−0.0100 (17)−0.0018 (18)−0.0051 (18)
C170.048 (2)0.055 (2)0.047 (3)−0.0150 (17)0.0027 (19)−0.0054 (18)
C180.078 (3)0.061 (3)0.058 (3)−0.028 (2)0.005 (2)0.007 (2)
C190.088 (3)0.060 (3)0.086 (4)−0.035 (2)0.009 (3)−0.001 (2)
C200.080 (3)0.064 (3)0.087 (4)−0.036 (2)0.014 (3)−0.025 (3)
C210.063 (3)0.063 (2)0.058 (3)−0.026 (2)0.002 (2)−0.017 (2)
C220.046 (2)0.050 (2)0.050 (2)−0.0155 (17)0.0051 (19)−0.0066 (18)
C230.049 (2)0.049 (2)0.037 (2)−0.0123 (17)−0.0034 (18)−0.0076 (17)
C240.057 (2)0.053 (2)0.053 (3)−0.0131 (18)−0.006 (2)−0.001 (2)
C25A0.066 (3)0.070 (3)0.042 (3)−0.013 (2)−0.002 (2)0.005 (2)
C26A0.074 (3)0.082 (3)0.049 (3)−0.001 (2)−0.014 (2)−0.009 (2)
C27A0.096 (4)0.112 (4)0.062 (4)−0.004 (3)−0.019 (3)−0.024 (3)
C28A0.126 (5)0.141 (6)0.052 (3)−0.001 (4)−0.001 (3)0.014 (3)
C29A0.136 (5)0.100 (4)0.091 (5)−0.023 (4)0.001 (4)0.030 (3)
C30A0.106 (4)0.100 (4)0.055 (3)−0.034 (3)−0.007 (3)0.021 (3)
C28B0.126 (5)0.141 (6)0.052 (3)−0.001 (4)−0.001 (3)0.014 (3)
C29B0.136 (5)0.100 (4)0.091 (5)−0.023 (4)0.001 (4)0.030 (3)
C30B0.106 (4)0.100 (4)0.055 (3)−0.034 (3)−0.007 (3)0.021 (3)
C26B0.074 (3)0.082 (3)0.049 (3)−0.001 (2)−0.014 (2)−0.009 (2)
F2B0.187 (5)0.156 (4)0.081 (3)−0.042 (4)−0.040 (3)−0.010 (3)
C25B0.066 (3)0.070 (3)0.042 (3)−0.013 (2)−0.002 (2)0.005 (2)
C27B0.096 (4)0.112 (4)0.062 (4)−0.004 (3)−0.019 (3)−0.024 (3)
S30.1131 (10)0.0550 (6)0.0586 (8)−0.0233 (6)−0.0331 (7)0.0093 (5)
F3A0.292 (18)0.175 (4)0.063 (3)−0.122 (11)−0.021 (8)−0.038 (3)
O30.088 (2)0.0521 (15)0.0539 (18)−0.0302 (14)−0.0128 (14)0.0043 (13)
N90.063 (2)0.0483 (18)0.051 (2)−0.0230 (15)−0.0094 (16)−0.0048 (15)
N100.0542 (19)0.0480 (17)0.0428 (19)−0.0165 (14)−0.0097 (15)0.0037 (14)
N110.067 (2)0.0447 (16)0.0403 (19)−0.0158 (14)−0.0100 (16)−0.0016 (14)
N120.077 (2)0.0442 (17)0.046 (2)−0.0190 (15)−0.0147 (16)0.0039 (14)
C310.053 (2)0.049 (2)0.047 (2)−0.0159 (17)0.0005 (19)−0.0039 (18)
C320.045 (2)0.053 (2)0.046 (2)−0.0153 (17)−0.0051 (18)−0.0034 (18)
C330.072 (3)0.065 (3)0.053 (3)−0.025 (2)−0.014 (2)−0.006 (2)
C340.095 (3)0.076 (3)0.048 (3)−0.025 (2)−0.024 (2)0.009 (2)
C350.098 (3)0.057 (2)0.057 (3)−0.025 (2)−0.018 (2)0.010 (2)
C360.074 (3)0.053 (2)0.053 (3)−0.0247 (19)−0.010 (2)−0.0001 (19)
C370.049 (2)0.044 (2)0.044 (2)−0.0145 (16)−0.0085 (18)−0.0027 (17)
C380.046 (2)0.046 (2)0.042 (2)−0.0139 (16)−0.0029 (18)−0.0028 (17)
C390.053 (2)0.054 (2)0.042 (2)−0.0142 (18)−0.0074 (18)−0.0043 (17)
C40A0.057 (4)0.047 (3)0.047 (3)−0.008 (2)−0.010 (3)−0.008 (2)
C41A0.025 (7)0.045 (5)0.076 (3)0.002 (5)−0.006 (5)−0.001 (3)
C42A0.087 (6)0.056 (4)0.122 (5)−0.026 (4)−0.022 (5)−0.006 (3)
C43A0.099 (7)0.071 (4)0.118 (5)−0.013 (4)−0.040 (5)−0.034 (3)
C44A0.090 (10)0.082 (6)0.060 (4)−0.004 (8)−0.035 (6)−0.017 (4)
C45A0.115 (9)0.065 (4)0.058 (4)−0.025 (5)−0.025 (5)−0.006 (3)
C43B0.099 (7)0.071 (4)0.118 (5)−0.013 (4)−0.040 (5)−0.034 (3)
C44B0.090 (10)0.082 (6)0.060 (4)−0.004 (8)−0.035 (6)−0.017 (4)
C45B0.115 (9)0.065 (4)0.058 (4)−0.025 (5)−0.025 (5)−0.006 (3)
C41B0.025 (7)0.045 (5)0.076 (3)0.002 (5)−0.006 (5)−0.001 (3)
F3B0.292 (18)0.175 (4)0.063 (3)−0.122 (11)−0.021 (8)−0.038 (3)
C40B0.057 (4)0.047 (3)0.047 (3)−0.008 (2)−0.010 (3)−0.008 (2)
C42B0.087 (6)0.056 (4)0.122 (5)−0.026 (4)−0.022 (5)−0.006 (3)

Geometric parameters (Å, °)

S1—C91.641 (4)C12A—H12A0.9300
S2—C241.650 (4)C12B—H12B0.9300
S3—C391.651 (4)C13A—H13A0.9300
F1A—C14A1.35 (12)C13B—H13B0.9300
F1B—C14B1.36 (16)C15A—H15A0.9300
F2A—C27A1.356 (6)C15B—H15B0.9300
F2B—C29B1.331 (5)C16—C231.495 (5)
F3A—C44A1.344 (18)C17—C181.376 (6)
F3B—C44B1.66 (4)C17—C221.394 (5)
O1—C11.217 (5)C18—C191.376 (6)
O2—C161.238 (5)C19—C201.377 (8)
O3—C311.241 (4)C20—C211.382 (6)
N1—C11.343 (5)C21—C221.374 (6)
N1—C21.398 (5)C22—C231.449 (5)
N2—C81.288 (4)C25A—C30A1.389 (6)
N2—N31.353 (4)C25A—C26A1.390 (6)
N3—C91.366 (4)C25B—C26B1.390 (4)
N4—C91.341 (5)C25B—C30B1.390 (4)
N4—C10B1.38 (2)C26A—C27A1.390 (5)
N4—C10A1.432 (16)C26B—C27B1.390 (5)
N1—H10.8600C27A—C28A1.390 (6)
N3—H3A0.8600C27B—C28B1.390 (4)
N4—H4A0.8600C28A—C29A1.390 (7)
N5—C161.338 (5)C28B—C29B1.390 (6)
N5—C171.410 (5)C29A—C30A1.390 (8)
N6—C231.295 (5)C29B—C30B1.390 (6)
N6—N71.338 (4)C18—H180.9300
N7—C241.390 (5)C19—H190.9300
N8—C25B1.396 (5)C20—H200.9300
N8—C241.328 (5)C21—H210.9300
N8—C25A1.391 (5)C26A—H26A0.9300
N5—H5A0.8600C26B—H26B0.9300
N7—H70.8600C27B—H27B0.9300
N8—H80.8600C28A—H28A0.9300
N9—C311.340 (4)C28B—H28B0.9300
N9—C321.413 (4)C29A—H29A0.9300
N10—C381.287 (4)C30A—H30A0.9300
N10—N111.351 (4)C30B—H30B0.9300
N11—C391.370 (5)C31—C381.496 (5)
N12—C40B1.45 (2)C32—C371.397 (5)
N12—C391.331 (5)C32—C331.362 (5)
N12—C40A1.379 (13)C33—C341.372 (6)
N9—H90.8600C34—C351.384 (6)
N11—H11C0.8600C35—C361.382 (6)
N12—H12C0.8600C36—C371.385 (5)
C1—C81.505 (5)C37—C381.442 (5)
C2—C31.368 (6)C40A—C41A1.390 (17)
C2—C71.392 (6)C40A—C45A1.391 (19)
C3—C41.369 (8)C40B—C41B1.39 (3)
C4—C51.375 (7)C40B—C45B1.39 (4)
C5—C61.391 (6)C41A—C42A1.390 (18)
C6—C71.374 (6)C41B—C42B1.39 (3)
C7—C81.443 (5)C42A—C43A1.39 (2)
C10A—C15A1.39 (2)C42B—C43B1.39 (4)
C10A—C11A1.39 (3)C43A—C44A1.39 (2)
C10B—C15B1.39 (3)C43B—C44B1.40 (4)
C10B—C11B1.39 (4)C44A—C45A1.39 (2)
C11A—C12A1.39 (3)C44B—C45B1.39 (3)
C11B—C12B1.39 (3)C33—H330.9300
C12A—C13A1.39 (3)C34—H340.9300
C12B—C13B1.39 (3)C35—H350.9300
C13A—C14A1.39 (3)C36—H360.9300
C13B—C14B1.39 (4)C41A—H41A0.9300
C14A—C15A1.39 (2)C41B—H41B0.9300
C14B—C15B1.39 (3)C42A—H42A0.9300
C3—H30.9300C42B—H42B0.9300
C4—H40.9300C43A—H43A0.9300
C5—H50.9300C43B—H43B0.9300
C6—H60.9300C45A—H45A0.9300
C11A—H11A0.9300C45B—H45B0.9300
C11B—H11B0.9300
S1···C15A3.223 (18)C23···C383.565 (4)
S1···C15B3.20 (2)C23···N113.406 (4)
S2···C30A3.208 (6)C23···C313.568 (5)
S2···N33.454 (3)C24···O13.401 (5)
S2···C30B3.195 (4)C24···C13.471 (6)
S2···C33i3.618 (4)C25A···C73.473 (6)
S3···C26A3.646 (4)C25A···C83.559 (6)
S3···C26B3.653 (3)C25B···C83.577 (5)
S3···C45B3.23 (2)C25B···C73.498 (6)
S3···C45A3.260 (13)C26A···C23.501 (6)
S1···H20ii2.9500C26A···C73.524 (6)
S1···H18iii2.9900C26A···S33.646 (4)
S1···H15B2.5400C26B···C73.532 (5)
S1···H15A2.5700C26B···C23.521 (5)
S2···H42Aii2.8700C26B···S33.653 (3)
S2···H33i2.9200C27A···C63.511 (6)
S2···H42Bii2.8000C27A···C27Av3.424 (5)
S2···H30B2.5300C27A···C53.406 (6)
S2···H34i3.1800C27B···C53.415 (6)
S2···H30A2.5400C27B···C63.507 (5)
S3···H26B3.1500C27B···C27Bv3.421 (5)
S3···H45A2.7200C28A···C63.542 (7)
S3···H3iv3.1400C28A···F2Av3.314 (7)
S3···H45B2.6200C28B···C63.551 (7)
S3···H28Av2.9600C30A···S23.208 (6)
S3···H83.1000C30A···C5iv3.597 (8)
S3···H26A3.1500C30B···C4iv3.588 (7)
S3···H28Bv2.9700C30B···S23.195 (4)
F2A···C4vi3.215 (7)C30B···C5iv3.567 (8)
F2A···C28Av3.314 (7)C31···C233.568 (5)
F2B···F3Av2.534 (17)C31···C163.247 (5)
F3A···F2Bv2.534 (17)C32···C20iv3.507 (6)
F3B···C11Av3.30 (3)C32···C19iv3.531 (6)
F1A···H21ii2.6200C33···C19iv3.484 (7)
F1B···H21ii2.7100C33···O1iii3.305 (5)
F2A···H4vi2.4800C33···C18iv3.472 (6)
F2B···H12Avii2.8000C33···S2i3.618 (4)
F3B···H11Av2.4600C34···O1iii3.405 (5)
O1···C243.401 (5)C36···C183.510 (6)
O1···N32.778 (4)C37···N53.428 (4)
O1···C34iii3.405 (5)C37···C20iv3.539 (5)
O1···N5iii2.881 (4)C37···C173.500 (5)
O1···N23.028 (4)C38···C163.552 (5)
O1···C33iii3.305 (5)C38···C223.510 (5)
O2···N63.032 (4)C38···N53.431 (4)
O2···N72.785 (4)C38···C233.565 (4)
O2···C16iii3.220 (4)C38···C173.420 (5)
O2···N9i2.871 (3)C39···C213.587 (5)
O3···N112.767 (3)C39···C15Ax3.280 (16)
O3···N1iv2.837 (3)C39···C14Ax3.565 (16)
O3···N103.020 (3)C40B···N4x3.31 (2)
O1···H5Aiii2.0500C41B···N2x3.37 (2)
O1···H3A2.1100C41B···C9x3.594 (18)
O2···H72.1100C42B···N2x3.39 (2)
O2···H9i2.0600C43B···C10Axi3.41 (3)
O3···H11C2.0900C43B···C11Axi3.23 (3)
O3···H1iv2.0300C44B···C11Axi3.28 (3)
O3···H3iv2.9200C44B···C12Axi3.27 (3)
N1···O3viii2.837 (3)C45A···S33.260 (13)
N2···O13.028 (4)C45B···S33.23 (2)
N2···N42.596 (4)C1···H3A2.4800
N2···C41Bix3.37 (2)C9···H15A2.8400
N2···C42Bix3.39 (2)C9···H15B2.9000
N3···O12.778 (4)C16···H72.4900
N3···S23.454 (3)C24···H30A2.8500
N4···C40Bix3.31 (2)C24···H30B2.8600
N4···N22.596 (4)C31···H11C2.4900
N5···C383.431 (4)C34···H41Bxii3.0800
N5···O1iii2.881 (4)C39···H45B2.9400
N5···C373.428 (4)C39···H45A2.8300
N6···O23.032 (4)C41B···H34xii3.0900
N6···N82.599 (4)H1···O3viii2.0300
N7···O22.785 (4)H3···O3viii2.9200
N8···N62.599 (4)H3···S3viii3.1400
N9···O2i2.871 (3)H3···H11Cviii2.5700
N10···N122.590 (4)H3A···C12.4800
N10···C223.248 (5)H3A···O12.1100
N10···O33.020 (3)H4···F2Avi2.4800
N11···C223.426 (5)H4A···H11A2.3800
N11···O32.767 (3)H4A···H11B2.1100
N11···C15Ax3.307 (17)H4A···N22.1300
N11···C233.406 (4)H5A···O1iii2.0500
N12···N102.590 (4)H7···H33i2.5100
N12···C15Ax3.348 (16)H7···O22.1100
N12···C10Bx3.399 (19)H7···C162.4900
N2···H4A2.1300H8···S33.1000
N6···H82.1400H8···N62.1400
N10···H15Ax2.8000H8···H26B2.2000
N10···H12C2.1300H8···H26A2.2000
N11···H15Ax2.9100H9···O2i2.0600
C1···C243.471 (6)H11A···H4A2.3800
C2···C26A3.501 (6)H11A···F3Bv2.4600
C2···C26B3.521 (5)H11B···H4A2.1100
C4···F2Avi3.215 (7)H11C···C312.4900
C4···C30Bviii3.588 (7)H11C···H3iv2.5700
C5···C27A3.406 (6)H11C···O32.0900
C5···C30Bviii3.567 (8)H12A···F2Bvii2.8000
C5···C30Aviii3.597 (8)H12C···H41A2.4400
C5···C27B3.415 (6)H12C···H41B2.2100
C6···C27A3.511 (6)H12C···N102.1300
C6···C27B3.507 (5)H15A···N11ix2.9100
C6···C28B3.551 (7)H15A···S12.5700
C6···C28A3.542 (7)H15A···C92.8400
C7···C26B3.532 (5)H15A···N10ix2.8000
C7···C26A3.524 (6)H15B···C92.9000
C7···C25A3.473 (6)H15B···S12.5400
C7···C25B3.498 (6)H18···S1iii2.9900
C8···C25A3.559 (6)H20···S1xi2.9500
C8···C25B3.577 (5)H21···F1Bxi2.7100
C9···C41Bix3.594 (18)H21···F1Axi2.6200
C10A···C43Bii3.41 (3)H26A···H82.2000
C10B···N12ix3.399 (19)H26A···S33.1500
C11A···C43Bii3.23 (3)H26B···S33.1500
C11A···F3Bv3.30 (3)H26B···H82.2000
C11A···C44Bii3.28 (3)H28A···S3v2.9600
C12A···C44Bii3.27 (3)H28B···S3v2.9700
C14A···C39ix3.565 (16)H30A···C242.8500
C15A···C39ix3.280 (16)H30A···S22.5400
C15A···N12ix3.348 (16)H30B···C242.8600
C15A···S13.223 (18)H30B···S22.5300
C15A···N11ix3.307 (17)H33···H7i2.5100
C15B···S13.20 (2)H33···S2i2.9200
C16···O2iii3.220 (4)H34···S2i3.1800
C16···C383.552 (5)H34···H41Axii2.5900
C16···C313.247 (5)H34···C41Bxii3.0900
C16···C16iii3.217 (5)H34···H41Bxii2.4400
C17···C383.420 (5)H36···H36xii2.5800
C17···C373.500 (5)H41A···H34xii2.5900
C18···C33viii3.472 (6)H41A···H12C2.4400
C18···C363.510 (6)H41B···C34xii3.0800
C19···C32viii3.531 (6)H41B···H34xii2.4400
C19···C33viii3.484 (7)H41B···H12C2.2100
C20···C32viii3.507 (6)H42A···S2xi2.8700
C20···C37viii3.539 (5)H42B···S2xi2.8000
C21···C393.587 (5)H45A···S32.7200
C22···C383.510 (5)H45A···C392.8300
C22···N103.248 (5)H45B···S32.6200
C22···N113.426 (5)H45B···C392.9400
C1—N1—C2111.9 (3)C16—C23—C22107.0 (3)
N3—N2—C8117.6 (3)N6—C23—C22124.8 (3)
N2—N3—C9121.8 (3)S2—C24—N7116.8 (3)
C9—N4—C10A131.9 (8)S2—C24—N8130.1 (3)
C9—N4—C10B130.5 (10)N7—C24—N8113.1 (3)
C1—N1—H1124.00N8—C25A—C30A124.4 (4)
C2—N1—H1124.00N8—C25A—C26A115.6 (3)
N2—N3—H3A119.00C26A—C25A—C30A120.0 (4)
C9—N3—H3A119.00C26B—C25B—C30B120.0 (3)
C10B—N4—H4A115.00N8—C25B—C26B114.9 (2)
C9—N4—H4A114.00N8—C25B—C30B125.2 (3)
C10A—N4—H4A114.00C25A—C26A—C27A120.0 (4)
C16—N5—C17111.7 (3)C25B—C26B—C27B120.0 (3)
N7—N6—C23117.9 (3)F2A—C27A—C26A117.6 (4)
N6—N7—C24120.8 (3)C26A—C27A—C28A120.0 (4)
C24—N8—C25A132.0 (3)F2A—C27A—C28A122.3 (3)
C24—N8—C25B131.1 (3)C26B—C27B—C28B120.0 (3)
C17—N5—H5A124.00C27A—C28A—C29A120.0 (4)
C16—N5—H5A124.00C27B—C28B—C29B120.0 (3)
C24—N7—H7120.00C28A—C29A—C30A120.0 (4)
N6—N7—H7120.00F2B—C29B—C30B112.7 (4)
C24—N8—H8114.00F2B—C29B—C28B127.3 (4)
C25A—N8—H8114.00C28B—C29B—C30B120.0 (3)
C25B—N8—H8115.00C25A—C30A—C29A120.0 (5)
C31—N9—C32111.3 (3)C25B—C30B—C29B120.0 (4)
N11—N10—C38117.8 (3)C19—C18—H18122.00
N10—N11—C39120.8 (3)C17—C18—H18122.00
C39—N12—C40B130.4 (10)C18—C19—H19119.00
C39—N12—C40A130.8 (6)C20—C19—H19119.00
C31—N9—H9124.00C21—C20—H20120.00
C32—N9—H9124.00C19—C20—H20120.00
C39—N11—H11C120.00C20—C21—H21121.00
N10—N11—H11C120.00C22—C21—H21121.00
C40B—N12—H12C114.00C27A—C26A—H26A120.00
C39—N12—H12C115.00C25A—C26A—H26A120.00
C40A—N12—H12C115.00C27B—C26B—H26B120.00
O1—C1—N1127.4 (4)C25B—C26B—H26B120.00
O1—C1—C8126.9 (4)C28B—C27B—H27B120.00
N1—C1—C8105.6 (3)C26B—C27B—H27B120.00
C3—C2—C7121.7 (4)C29A—C28A—H28A120.00
N1—C2—C3128.9 (4)C27A—C28A—H28A120.00
N1—C2—C7109.3 (3)C27B—C28B—H28B120.00
C2—C3—C4117.9 (4)C29B—C28B—H28B120.00
C3—C4—C5121.4 (5)C28A—C29A—H29A120.00
C4—C5—C6120.9 (5)C30A—C29A—H29A120.00
C5—C6—C7118.0 (4)C29A—C30A—H30A120.00
C2—C7—C8106.8 (3)C25A—C30A—H30A120.00
C2—C7—C6120.2 (4)C25B—C30B—H30B120.00
C6—C7—C8133.1 (4)C29B—C30B—H30B120.00
N2—C8—C7125.7 (3)O3—C31—N9127.5 (3)
N2—C8—C1127.9 (3)O3—C31—C38126.0 (3)
C1—C8—C7106.4 (3)N9—C31—C38106.6 (3)
S1—C9—N4129.3 (3)N9—C32—C33128.5 (3)
N3—C9—N4112.6 (3)N9—C32—C37108.9 (3)
S1—C9—N3118.1 (3)C33—C32—C37122.6 (4)
C11A—C10A—C15A120.0 (15)C32—C33—C34117.2 (4)
N4—C10A—C11A118.8 (14)C33—C34—C35122.2 (4)
N4—C10A—C15A120.7 (15)C34—C35—C36120.0 (4)
N4—C10B—C11B112.3 (17)C35—C36—C37118.8 (4)
C11B—C10B—C15B120.1 (19)C32—C37—C36119.2 (3)
N4—C10B—C15B127 (2)C36—C37—C38133.8 (3)
C10A—C11A—C12A120.0 (16)C32—C37—C38107.0 (3)
C10B—C11B—C12B120 (2)N10—C38—C37125.5 (3)
C11A—C12A—C13A120.0 (17)C31—C38—C37106.4 (3)
C11B—C12B—C13B120 (2)N10—C38—C31128.2 (3)
C12A—C13A—C14A120.0 (15)S3—C39—N11117.9 (3)
C12B—C13B—C14B120.1 (19)S3—C39—N12128.8 (3)
F1A—C14A—C15A121 (6)N11—C39—N12113.3 (3)
F1A—C14A—C13A116 (6)N12—C40A—C41A119.5 (11)
C13A—C14A—C15A120.0 (15)N12—C40A—C45A119.7 (10)
F1B—C14B—C13B119 (7)C41A—C40A—C45A120.0 (11)
C13B—C14B—C15B120.0 (18)N12—C40B—C45B126.4 (18)
F1B—C14B—C15B115 (7)N12—C40B—C41B112.7 (19)
C10A—C15A—C14A120.1 (16)C41B—C40B—C45B120 (2)
C10B—C15B—C14B120 (2)C40A—C41A—C42A120.0 (12)
C4—C3—H3121.00C40B—C41B—C42B120 (2)
C2—C3—H3121.00C41A—C42A—C43A120.0 (12)
C3—C4—H4119.00C41B—C42B—C43B120 (2)
C5—C4—H4119.00C42A—C43A—C44A120.0 (12)
C4—C5—H5120.00C42B—C43B—C44B120 (2)
C6—C5—H5120.00C43A—C44A—C45A120.0 (12)
C7—C6—H6121.00F3A—C44A—C43A107.4 (14)
C5—C6—H6121.00F3A—C44A—C45A125.4 (15)
C10A—C11A—H11A120.00F3B—C44B—C45B98 (2)
C12A—C11A—H11A120.00F3B—C44B—C43B122 (2)
C10B—C11B—H11B120.00C43B—C44B—C45B120 (2)
C12B—C11B—H11B120.00C40A—C45A—C44A120.0 (12)
C11A—C12A—H12A120.00C40B—C45B—C44B120 (2)
C13A—C12A—H12A120.00C32—C33—H33121.00
C13B—C12B—H12B120.00C34—C33—H33121.00
C11B—C12B—H12B120.00C33—C34—H34119.00
C14A—C13A—H13A120.00C35—C34—H34119.00
C12A—C13A—H13A120.00C34—C35—H35120.00
C14B—C13B—H13B120.00C36—C35—H35120.00
C12B—C13B—H13B120.00C35—C36—H36121.00
C10A—C15A—H15A120.00C37—C36—H36121.00
C14A—C15A—H15A120.00C40A—C41A—H41A120.00
C14B—C15B—H15B120.00C42A—C41A—H41A120.00
C10B—C15B—H15B120.00C42B—C41B—H41B120.00
N5—C16—C23105.9 (3)C40B—C41B—H41B120.00
O2—C16—N5127.6 (3)C43A—C42A—H42A120.00
O2—C16—C23126.5 (3)C41A—C42A—H42A120.00
N5—C17—C22109.3 (3)C43B—C42B—H42B120.00
N5—C17—C18128.6 (3)C41B—C42B—H42B120.00
C18—C17—C22122.1 (4)C44A—C43A—H43A120.00
C17—C18—C19116.5 (4)C42A—C43A—H43A120.00
C18—C19—C20122.3 (4)C44B—C43B—H43B120.00
C19—C20—C21120.8 (4)C42B—C43B—H43B120.00
C20—C21—C22118.0 (4)C44A—C45A—H45A120.00
C21—C22—C23133.5 (4)C40A—C45A—H45A120.00
C17—C22—C23106.1 (3)C40B—C45B—H45B120.00
C17—C22—C21120.4 (4)C44B—C45B—H45B120.00
N6—C23—C16128.2 (3)
C2—N1—C1—O1−178.5 (4)C11A—C12A—C13A—C14A0(2)
C2—N1—C1—C8−0.4 (4)C12A—C13A—C14A—F1A161 (4)
C1—N1—C2—C3−179.8 (4)C12A—C13A—C14A—C15A0(2)
C1—N1—C2—C70.0 (5)C13A—C14A—C15A—C10A0(2)
C8—N2—N3—C9173.8 (3)F1A—C14A—C15A—C10A−160 (4)
N3—N2—C8—C1−2.7 (5)O2—C16—C23—N62.3 (6)
N3—N2—C8—C7178.0 (3)N5—C16—C23—N6−176.6 (3)
N2—N3—C9—S1178.8 (3)N5—C16—C23—C221.7 (4)
N2—N3—C9—N4−1.0 (5)O2—C16—C23—C22−179.5 (3)
C10A—N4—C9—S12.8 (10)N5—C17—C18—C19−178.1 (4)
C10A—N4—C9—N3−177.4 (9)C18—C17—C22—C23−178.0 (3)
C9—N4—C10A—C11A161.3 (10)N5—C17—C22—C21178.2 (3)
C9—N4—C10A—C15A−26.6 (19)N5—C17—C22—C23−0.1 (4)
C16—N5—C17—C18179.0 (4)C22—C17—C18—C19−0.6 (6)
C16—N5—C17—C221.2 (4)C18—C17—C22—C210.3 (6)
C17—N5—C16—C23−1.8 (4)C17—C18—C19—C200.9 (7)
C17—N5—C16—O2179.4 (4)C18—C19—C20—C21−0.9 (7)
N7—N6—C23—C16−1.7 (5)C19—C20—C21—C220.5 (6)
C23—N6—N7—C24179.6 (3)C20—C21—C22—C17−0.2 (6)
N7—N6—C23—C22−179.7 (3)C20—C21—C22—C23177.6 (4)
N6—N7—C24—N8−6.0 (5)C17—C22—C23—N6177.4 (3)
N6—N7—C24—S2173.4 (3)C17—C22—C23—C16−0.9 (4)
C24—N8—C25A—C26A−172.7 (4)C21—C22—C23—C16−178.9 (4)
C24—N8—C25A—C30A8.5 (8)C21—C22—C23—N6−0.6 (7)
C25A—N8—C24—S2−1.6 (7)C30A—C25A—C26A—C27A0.0 (7)
C25A—N8—C24—N7177.7 (4)N8—C25A—C26A—C27A−178.9 (4)
C31—N9—C32—C370.3 (4)C26A—C25A—C30A—C29A0.0 (8)
C31—N9—C32—C33−179.2 (4)N8—C25A—C30A—C29A178.9 (5)
C32—N9—C31—O3−179.6 (3)C25A—C26A—C27A—F2A−176.5 (4)
C32—N9—C31—C38−0.3 (4)C25A—C26A—C27A—C28A0.0 (6)
N11—N10—C38—C31−1.1 (5)C26A—C27A—C28A—C29A0.0 (7)
C38—N10—N11—C39178.7 (3)F2A—C27A—C28A—C29A176.3 (5)
N11—N10—C38—C37177.1 (3)C27A—C28A—C29A—C30A0.0 (9)
N10—N11—C39—S3176.3 (3)C28A—C29A—C30A—C25A0.0 (9)
N10—N11—C39—N12−3.4 (5)O3—C31—C38—N10−1.9 (6)
C40A—N12—C39—S30.2 (9)O3—C31—C38—C37179.6 (3)
C39—N12—C40A—C45A41.9 (14)N9—C31—C38—N10178.8 (3)
C40A—N12—C39—N11180.0 (8)N9—C31—C38—C370.3 (4)
C39—N12—C40A—C41A−148.3 (8)N9—C32—C33—C34180.0 (4)
N1—C1—C8—C70.6 (4)C37—C32—C33—C340.6 (6)
N1—C1—C8—N2−178.7 (4)N9—C32—C37—C36−179.6 (3)
O1—C1—C8—N2−0.6 (7)N9—C32—C37—C38−0.1 (4)
O1—C1—C8—C7178.8 (4)C33—C32—C37—C36−0.1 (6)
C7—C2—C3—C4−0.1 (7)C33—C32—C37—C38179.5 (3)
N1—C2—C3—C4179.7 (4)C32—C33—C34—C35−0.9 (7)
N1—C2—C7—C6179.8 (4)C33—C34—C35—C360.8 (7)
N1—C2—C7—C80.4 (5)C34—C35—C36—C37−0.4 (6)
C3—C2—C7—C8−179.8 (4)C35—C36—C37—C320.0 (6)
C3—C2—C7—C6−0.4 (6)C35—C36—C37—C38−179.4 (4)
C2—C3—C4—C50.5 (7)C32—C37—C38—N10−178.7 (3)
C3—C4—C5—C6−0.4 (7)C32—C37—C38—C31−0.1 (4)
C4—C5—C6—C7−0.1 (7)C36—C37—C38—N100.8 (6)
C5—C6—C7—C8179.6 (4)C36—C37—C38—C31179.3 (4)
C5—C6—C7—C20.5 (6)N12—C40A—C41A—C42A−169.7 (10)
C2—C7—C8—N2178.8 (4)C45A—C40A—C41A—C42A0.0 (18)
C6—C7—C8—C1−179.9 (5)N12—C40A—C45A—C44A169.7 (11)
C6—C7—C8—N2−0.5 (7)C41A—C40A—C45A—C44A0.0 (19)
C2—C7—C8—C1−0.7 (4)C40A—C41A—C42A—C43A0.0 (18)
C11A—C10A—C15A—C14A0(2)C41A—C42A—C43A—C44A0(2)
N4—C10A—C15A—C14A−172.1 (13)C42A—C43A—C44A—F3A−152.0 (14)
C15A—C10A—C11A—C12A0(2)C42A—C43A—C44A—C45A0(2)
N4—C10A—C11A—C12A172.5 (14)F3A—C44A—C45A—C40A146.6 (15)
C10A—C11A—C12A—C13A−1(3)C43A—C44A—C45A—C40A0(2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z; (v) −x+1, −y+1, −z; (vi) −x, −y+1, −z; (vii) −x+1, −y+2, −z; (viii) x−1, y, z; (ix) x−1, y+1, z; (x) x+1, y−1, z; (xi) x, y−1, z; (xii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O3viii0.862.032.837 (3)155
N3—H3A···O10.862.112.778 (4)134
N4—H4A···N20.862.132.596 (4)114
N5—H5A···O1iii0.862.052.881 (4)164
N7—H7···O20.862.112.785 (4)135
N8—H8···N60.862.142.599 (4)113
N9—H9···O2i0.862.062.871 (3)157
N11—H11C···O30.862.092.767 (3)135
N12—H12C···N100.862.132.590 (4)113
C4—H4···F2Avi0.932.483.215 (7)136
C15A—H15A···S10.932.573.223 (18)127
C30A—H30A···S20.932.543.208 (6)129
C42A—H42A···S2xi0.932.873.763 (12)162
C45A—H45A···S30.932.723.260 (13)118

Symmetry codes: (viii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (i) −x+2, −y+1, −z+1; (vi) −x, −y+1, −z; (xi) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2363).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Pervez, H., Chohan, Z. H., Ramzan, M., Nasim, F. H. & Khan, K. M. (2009). J. Enz. Inhib. Med. Chem 24, 437–446. [PubMed]
  • Pervez, H., Iqbal, M. S., Tahir, M. Y., Choudhary, M. I. & Khan, K. M. (2007). Nat. Prod. Res 21, 1178–1186. [PubMed]
  • Pervez, H., Iqbal, M. S., Tahir, M. Y., Nasim, F. H., Choudhary, M. I. & Khan, K. M. (2008). J. Enz. Inhib. Med. Chem.23, 848–854. [PubMed]
  • Pervez, H., Yaqub, M., Ramzan, M., Iqbal, M. S. & Tahir, M. N. (2010). Acta Cryst. E66, o1018. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography