PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o481–o482.
Published online 2008 January 23. doi:  10.1107/S1600536808000561
PMCID: PMC2960448

Bis{4-[(Z)-N′-(4-hydroxy­benzyl­idene)hydrazino]-8-(trifluoro­meth­yl)quinolinium} sulfate dihydrate

Abstract

The title compound, 2C17H13F3N3O+·SO4 2−·2H2O, crystallizes with four independent cations (A, B, C and D) in the asymmetric unit, which is composed of two groups of two cations, one anion and two water mol­ecules (Z′ = 2). The dihedral angle between the mean planes of the 4-hydroxy­phenyl and quinolinium groups is 8.9 (7)° in A, 30.1 (6)° in B, 28.8 (8)° in C and 12.8 (1)° in D. The crystal packing is stabilized by inter­molecular O—H(...)O and N—H(...)O hydrogen bonding between H atoms from 4-hydroxy­phenyl O atoms and the O atoms of nearby water molecules and sulfate anions, as well as H atoms from the N atom of the hydrazino group to O atoms of neighboring sulfate anions, linking the components into chains with the 4-hydroxy­phenyl and quinolinium rings parallel to the (011) plane. There is also an extensive array of inter­molecular hydrogen bonds between water mol­ecules themselves and with sulfate O atoms, as well as hydrogen-bond inter­actions between H atoms from the hydrazino group and sulfate O atoms. In addition, inter­molecular π–π stacking inter­actions occur between nearby 4-hydroxy­phenyl and quinolinium groups, with distances between the centroids of inter­acting rings in the range 3.4140 (9)–3.9659 (9) Å.

Related literature

For related structures, see: Yathirajan et al. (2007 [triangle]); Fun et al. (1999 [triangle]); Wang et al. (1998 [triangle]); Sadık et al. (2004 [triangle]). For related literature, see: Roma et al. (2000 [triangle]); Chen et al. (2001 [triangle]); Maguire et al. (1994 [triangle]); Zhang et al. (2000 [triangle]); Kahwa et al. (1986 [triangle]); Santos et al. (2001 [triangle]); Saim et al. (2004 [triangle]); El-Masry et al. (2000 [triangle]); Pandey et al. (1999 [triangle]); Hodnett et al. (1970 [triangle]); Misra et al. (1981 [triangle]); Varma et al. (1986 [triangle]); Singh et al. (1988 [triangle]); Desai et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o481-scheme1.jpg

Experimental

Crystal data

  • 2C17H13F3N3O+·SO4 2−·2H2O
  • M r = 796.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o481-efi1.jpg
  • a = 13.4349 (1) Å
  • b = 23.8601 (1) Å
  • c = 21.7174 (1) Å
  • β = 96.8568 (4)°
  • V = 6911.89 (7) Å3
  • Z = 8
  • Cu Kα radiation
  • μ = 1.68 mm−1
  • T = 200 (2) K
  • 0.55 × 0.37 × 0.19 mm

Data collection

  • Oxford Diffraction Gemini R CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.441, T max = 0.727
  • 45529 measured reflections
  • 13742 independent reflections
  • 11290 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.127
  • S = 1.05
  • 13742 reflections
  • 1020 parameters
  • 12 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.74 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000561/nc2084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000561/nc2084Isup2.hkl

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

Acknowledgments

KS thanks the Department of Chemistry, Mangalore University, for use of their research facilities. RJB acknow­ledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

It is well known that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with interesting biological activities (Roma et al. 2000 and Chen et al. 2001). A large variety of quinoline derivatives have been used as antimalarial, anti-inflammatory agents, antiasthmatic, antibacterial, antihypertensive and tyrokinase PDGF-RTK inhibiting agents (Maguire et al. 1994). Furthermore, poly-substituted quinolines have been found to undergo hierarchical self-assembly into a variety of nano- and mesostructures with enhanced electronic and photonic functions (Zhang et al. 2000). The synthesis and structure of Schiff bases have attracted much attention in biology and chemistry (Kahwa et al. 1986). One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al. 2001). Structural information is useful in investigating the coordination properties of Schiff bases functioning as ligands (Saim et al. 2004). Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial (El-Masry et al.. 2000 & Pandey et al. 1999), antifungal (Singh et al. 1988 & Varma et al. 1986), antitumor (Hodnett et al. 1970; Misra et al. 1981 & Desai et al. 2001), and as herbicides. The crystal structures of Schiff base compounds, viz, bis{4-[(2-hydroxybenzylidine)hydrazino]-8-(trifluoromethyl)quinolinium} sulfate tetrahydrate, (Yathirajan et al. 2007), p-hydroxybenzaldehyde nicotinoylhydrazone monohydrate (Fun et al. 1999), 2-(2-hydroxybenzylidene)-1-(2-picoloyl)hydrazine hemihydrate (Wang et al. 1998), 5-bromo-2-hydroxybenzaldehyde (4-phenyl-1,3-thiazol-2-yl)hydrazone (Sadık et al. 2004) have been reported. A new Schiff base, C34H30F6N6O8S, was synthesized and its crystal structure is reported.

The title compound, C34H30F6N6O8S, crystallizes with four independent cations (A, B, C and D) in the asymmetric unit which is composed of two groups of two cations, one anion and two water molecules [Z'= 2], respectively (Figs. 1–2). The dihedral angle between the mean planes of the 4-hydroxyphenyl and quinolinium groups is 8.9 (7)° in A, 30.1 (6)° in B, 28.8 (8)° in C and 12.8 (1)° in D. Crystal packing is stabilized by intermolecular O—H···O and N—H···O hydrogen bonding between H atoms from 4-hydroxyphenyl oxygen atoms and oxygen atoms from nearby water and sulfate molecules as well as H atoms from the nitrogen atom of the hydrazino group to oxygen atoms from neighboring sulfate molecules linking the molecules into chains with the 4-hydroxyphenyl and quinolimium rings parallel to the [011] plane of the unit cell (Fig. 3). There is also an extensive array of intermolecular hydrogen bonds between water molecules themselves and with sulfate oxygen atoms,in the unit cell as well as hydrogen bond interactions between hydrogen atoms from the hydrazino group and sulfate oxygen atoms. Also, intermolecular π-π stacking interactions occur between adjacent 4-hydroxyphenyl and quinolinium rings as follows: [Cg1, Cg2, Cg3, Cg5, Cg6, Cg9, Cg10, Cg13, Cg14 & Cg15 = center of gravity of (N1A, C5A–C9A), (C1A–C5A, C9A), (C12A–C17A), (N1B, C5B–C9B), (C1B–C5B, C9B), (N1C, C5C–C9C), (C1C–C5C, C9C), (N1C, C5C–C9C), (C1D–C5D, C9D), (C12D–C17D); Cg1···Cg13 = 3.7262 (9) & 3.4140 (9)ix Å; Cg2···Cg13 = 3.5888 (9)ix Å; Cg2···Cg14 = 3.9659 (9)ix Å; Cg3···Cg15 = 3.9401 (10)ix Å; Cg5···Cg9 = 3.5848 (8)ix & 3.6314 (9)x Å; Cg6···Cg9 = 3.8223 (9)ix & 3.5486 (9)x Å; Cg6···Cg10 = 3.6649 (9)xi Å; ix = x, y, z; x = 1/2 - x, 1/2 - y, z; xi = -1/2 + x, 1/2 - y, z].

Experimental

A mixture of 4-hydrazino-8-(trifluoromethyl)quinoline (1.135 g, 0.005 mol) and 4-hydroxybenzaldehyde (0.61 g, 0.005 mol) in 15 ml of absolute alcohol containing 2 drops of sulfuric acid was refluxed for about 3 h. On cooling, the solid separated, was filtered and recrystallized from DMF (m.p.: Above 523 K).

Refinement

The hydroxyl hydrogen atoms (H1A, H1B, H1C, H1D) and the amine hydrogen atoms (H1AA, H2AB, H1BA, H2BB, H1CA, H2CB, H1DA, H2DB) were located in a difference Fourier map and refined using the riding model with O—H = 0.84 Å, N—H = 0.88 Å. All other H atoms in cations A, B, C & D were placed in their calculated positions and then refined using the riding model with C—H = 0.95 Å, and with Uiso(H) = 1.18–1.21Ueq(C, N, O). O–H bonds and H–H distances in each of the water molecules were refined with restraints at 0.82 Å and 1.297 Å, respectively.

Figures

Fig. 1.
Molecular structure of molecules A & D, a sulfate ion and 3 water molecules in a partial description of the asymmetric unit for the title compound, showing atom labeling and 30% probability displacement ellipsoids.
Fig. 2.
Molecular structure of molecules B & C, a sulfate ion and 1 water molecule in a partial description of the asymmetric unit for the title compound, showing atom labeling and 30% probability displacement ellipsoids.
Fig. 3.
Packing diagram of the title compound, viewed down the c axis. Dashed lines indicate intermolecular O—H···O and N—H···O hydrogen bonds.

Crystal data

2C17H13F3N3O+·S1O42–·2H2OF000 = 3280
Mr = 796.70Dx = 1.531 Mg m3
Monoclinic, P21/aCu Kα radiation λ = 1.54184 Å
Hall symbol: -P 2yabCell parameters from 28034 reflections
a = 13.4349 (1) Åθ = 4.1–73.8º
b = 23.8601 (1) ŵ = 1.68 mm1
c = 21.7174 (1) ÅT = 200 (2) K
β = 96.8568 (4)ºThick plate, yellow
V = 6911.89 (7) Å30.55 × 0.37 × 0.19 mm
Z = 8

Data collection

Oxford Diffraction Gemini R CCD diffractometer13742 independent reflections
Radiation source: fine-focus sealed tube11290 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
Detector resolution: 10.5081 pixels mm-1θmax = 74.1º
T = 200(2) Kθmin = 4.1º
[var phi] and ω scansh = −16→15
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −29→29
Tmin = 0.441, Tmax = 0.727l = −27→27
45529 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)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127  w = 1/[σ2(Fo2) + (0.0961P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
13742 reflectionsΔρmax = 0.74 e Å3
1020 parametersΔρmin = −0.41 e Å3
12 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
S10.66689 (3)0.187616 (15)0.499522 (16)0.02836 (10)
S20.75736 (3)0.264569 (16)0.980196 (16)0.03112 (10)
F1A0.38287 (9)0.60885 (6)0.16001 (6)0.0492 (3)
F2A0.23142 (8)0.62688 (5)0.17582 (6)0.0456 (3)
F3A0.30734 (11)0.55656 (5)0.22072 (6)0.0549 (3)
F1B0.77439 (9)0.30958 (6)0.39611 (5)0.0505 (3)
F2B0.61525 (9)0.32051 (5)0.38017 (5)0.0454 (3)
F3B0.71268 (11)0.39064 (5)0.37049 (6)0.0528 (3)
F1C0.52317 (9)0.42538 (5)0.29453 (6)0.0497 (3)
F2C0.36467 (9)0.43361 (5)0.27143 (7)0.0504 (3)
F3C0.46481 (11)0.48564 (5)0.22683 (7)0.0548 (3)
F1D0.72434 (11)0.57600 (6)0.15532 (6)0.0581 (3)
F2D0.56809 (9)0.55653 (5)0.14721 (5)0.0463 (3)
F3D0.67439 (11)0.49953 (5)0.19391 (6)0.0552 (3)
O1A0.48294 (10)1.15354 (5)0.36284 (6)0.0369 (3)
H1A0.52221.16370.39380.044*
O1B0.82685 (15)−0.10351 (6)−0.01295 (9)0.0600 (4)
H1B0.8211−0.12740.01490.072*
O1C0.51549 (11)−0.12665 (6)0.14066 (7)0.0439 (3)
H1C0.5018−0.14420.10720.053*
O1D0.72708 (11)1.07763 (5)0.40646 (6)0.0399 (3)
H1D0.72631.09100.44220.048*
O110.57717 (10)0.19361 (6)0.53218 (6)0.0402 (3)
O120.63883 (10)0.19895 (5)0.43294 (5)0.0365 (3)
O130.70470 (11)0.12950 (5)0.50799 (6)0.0411 (3)
O140.74565 (10)0.22713 (5)0.52553 (6)0.0391 (3)
O210.70265 (11)0.30509 (5)0.93705 (6)0.0419 (3)
O220.68867 (11)0.24572 (6)1.02472 (6)0.0435 (3)
O230.84557 (12)0.29237 (7)1.01441 (6)0.0494 (3)
O240.78908 (12)0.21622 (6)0.94591 (7)0.0490 (3)
O1W0.53785 (14)0.66106 (7)0.06907 (7)0.0520 (4)
H1W10.5842 (17)0.6790 (13)0.0585 (16)0.078*
H1W20.4867 (15)0.6696 (15)0.0473 (15)0.078*
O2W0.39849 (12)0.35357 (7)0.38120 (7)0.0516 (4)
H2W10.353 (2)0.3742 (12)0.3894 (15)0.077*
H2W20.410 (2)0.3341 (13)0.4128 (12)0.077*
O3W0.48321 (15)0.80476 (10)0.04431 (11)0.0758 (6)
H3W10.5343 (19)0.802 (2)0.0270 (19)0.114*
H3W20.438 (2)0.7906 (19)0.0191 (17)0.114*
O4W0.56157 (16)0.71447 (10)0.51613 (13)0.0818 (7)
H4W10.532 (3)0.7452 (12)0.515 (2)0.123*
H4W20.6178 (18)0.7226 (18)0.508 (2)0.123*
N1A0.34199 (10)0.72867 (6)0.18977 (6)0.0309 (3)
H1AA0.32570.70680.15750.037*
N2A0.40367 (10)0.83468 (6)0.33901 (6)0.0296 (3)
H2AB0.41180.82170.37720.036*
N3A0.40772 (10)0.89174 (6)0.32737 (6)0.0310 (3)
N1B0.68578 (10)0.22189 (6)0.31392 (6)0.0291 (3)
H1BA0.68370.23000.35330.035*
N2B0.69915 (10)0.17935 (6)0.13111 (6)0.0279 (3)
H2BB0.69840.20500.10190.034*
N3B0.70759 (10)0.12263 (6)0.11726 (6)0.0301 (3)
N1C0.43842 (10)0.31498 (6)0.27005 (6)0.0295 (3)
H1CA0.43130.33980.29920.035*
N2C0.44382 (10)0.19512 (6)0.13377 (6)0.0300 (3)
H2CB0.43410.20470.09440.036*
N3C0.45725 (10)0.13929 (6)0.15104 (6)0.0315 (3)
N1D0.60597 (10)0.67250 (6)0.19298 (6)0.0308 (3)
H1DA0.59540.65440.15750.037*
N2D0.65741 (10)0.76047 (5)0.35705 (6)0.0280 (3)
H2DB0.67030.74290.39280.034*
N3D0.65647 (10)0.81849 (5)0.35395 (6)0.0290 (3)
C1A0.35732 (12)0.64644 (7)0.25706 (8)0.0320 (3)
C2A0.38460 (13)0.62364 (7)0.31475 (8)0.0350 (3)
H2AA0.38410.58410.32010.042*
C3A0.41310 (13)0.65853 (8)0.36574 (8)0.0349 (3)
H3AA0.43330.64250.40530.042*
C4A0.41202 (12)0.71545 (7)0.35901 (7)0.0305 (3)
H4AA0.42840.73870.39430.037*
C5A0.38664 (11)0.74009 (7)0.29990 (7)0.0266 (3)
C6A0.38709 (11)0.80012 (7)0.29088 (7)0.0274 (3)
C7A0.36927 (12)0.82069 (7)0.22972 (7)0.0314 (3)
H7AA0.37240.85980.22210.038*
C8A0.34752 (13)0.78431 (8)0.18157 (7)0.0328 (3)
H8AA0.33580.79890.14060.039*
C9A0.36138 (11)0.70516 (7)0.24806 (7)0.0286 (3)
C10A0.32063 (13)0.60916 (8)0.20370 (9)0.0369 (4)
C11A0.41583 (13)0.92246 (7)0.37550 (8)0.0337 (3)
H11A0.41660.90560.41520.040*
C12A0.42402 (12)0.98322 (7)0.37085 (7)0.0320 (3)
C13A0.41453 (13)1.01174 (7)0.31441 (7)0.0335 (3)
H13A0.39530.99200.27690.040*
C14A0.43297 (13)1.06857 (7)0.31306 (7)0.0346 (3)
H14A0.42561.08780.27450.042*
C15A0.46239 (12)1.09814 (7)0.36776 (7)0.0301 (3)
C16A0.46704 (15)1.07083 (8)0.42426 (8)0.0397 (4)
H16A0.48421.09080.46190.048*
C17A0.44635 (16)1.01388 (8)0.42514 (8)0.0419 (4)
H17A0.44750.99530.46390.050*
C1B0.70261 (11)0.32146 (7)0.29216 (7)0.0309 (3)
C2B0.71193 (12)0.36314 (7)0.24994 (8)0.0336 (3)
H2BA0.71820.40090.26360.040*
C3B0.71234 (12)0.35092 (7)0.18666 (8)0.0326 (3)
H3BA0.71810.38030.15780.039*
C4B0.70436 (11)0.29630 (7)0.16667 (7)0.0287 (3)
H4BA0.70450.28820.12380.034*
C5B0.69594 (10)0.25208 (7)0.20877 (7)0.0255 (3)
C6B0.69224 (10)0.19367 (7)0.18988 (7)0.0260 (3)
C7B0.68425 (12)0.15244 (7)0.23553 (7)0.0295 (3)
H7BA0.68130.11390.22450.035*
C8B0.68081 (11)0.16813 (7)0.29590 (7)0.0298 (3)
H8BA0.67470.13990.32610.036*
C9B0.69409 (10)0.26466 (7)0.27264 (7)0.0263 (3)
C10B0.70130 (13)0.33571 (8)0.35973 (8)0.0370 (4)
C11B0.73397 (12)0.11286 (7)0.06376 (7)0.0314 (3)
H11B0.74110.14310.03620.038*
C12B0.75329 (13)0.05546 (7)0.04440 (7)0.0312 (3)
C13B0.72313 (12)0.00811 (7)0.07544 (7)0.0323 (3)
H13B0.68660.01280.11000.039*
C14B0.74556 (13)−0.04518 (7)0.05668 (8)0.0349 (3)
H14B0.7228−0.07700.07730.042*
C15B0.80194 (15)−0.05220 (8)0.00714 (9)0.0414 (4)
C16B0.83228 (18)−0.00535 (9)−0.02404 (10)0.0491 (5)
H16B0.8705−0.0100−0.05780.059*
C17B0.80718 (16)0.04761 (8)−0.00628 (8)0.0416 (4)
H17B0.82660.0792−0.02860.050*
C1C0.45406 (12)0.39089 (7)0.19689 (8)0.0331 (3)
C2C0.46737 (13)0.40745 (7)0.13768 (9)0.0378 (4)
H2CA0.47260.44620.12870.045*
C3C0.47331 (14)0.36817 (8)0.09071 (8)0.0387 (4)
H3CA0.48410.38030.05040.046*
C4C0.46365 (13)0.31206 (7)0.10262 (8)0.0339 (3)
H4CA0.46630.28560.07010.041*
C5C0.44977 (11)0.29300 (7)0.16300 (7)0.0277 (3)
C6C0.44602 (11)0.23400 (7)0.17822 (7)0.0272 (3)
C7C0.44761 (11)0.21926 (7)0.24094 (7)0.0280 (3)
H7CA0.45310.18100.25320.034*
C8C0.44122 (11)0.26022 (7)0.28428 (7)0.0284 (3)
H8CA0.43870.24950.32620.034*
C9C0.44641 (11)0.33293 (7)0.21064 (7)0.0282 (3)
C10C0.45138 (14)0.43391 (7)0.24691 (10)0.0388 (4)
C11C0.44711 (13)0.10421 (7)0.10625 (8)0.0338 (3)
H11C0.42700.11740.06540.041*
C12C0.46553 (12)0.04426 (7)0.11611 (8)0.0329 (3)
C13C0.50844 (14)0.02223 (8)0.17285 (8)0.0368 (3)
H13C0.52680.04670.20680.044*
C14C0.52437 (15)−0.03457 (8)0.18002 (8)0.0398 (4)
H14C0.5533−0.04890.21890.048*
C15C0.49837 (13)−0.07113 (7)0.13077 (8)0.0349 (3)
C16C0.45736 (15)−0.04976 (8)0.07377 (9)0.0435 (4)
H16C0.4403−0.07420.03960.052*
C17C0.44146 (15)0.00738 (8)0.06702 (9)0.0430 (4)
H17C0.41350.02170.02790.052*
C1D0.64734 (12)0.58375 (7)0.24630 (8)0.0314 (3)
C2D0.66576 (13)0.55508 (7)0.30099 (9)0.0357 (3)
H2DA0.67490.51560.30030.043*
C3D0.67130 (13)0.58297 (7)0.35787 (8)0.0350 (3)
H3DA0.68150.56230.39550.042*
C4D0.66203 (12)0.64020 (7)0.35952 (7)0.0297 (3)
H4DA0.66830.65900.39830.036*
C5D0.64323 (11)0.67139 (6)0.30411 (7)0.0264 (3)
C6D0.63804 (11)0.73205 (6)0.30392 (7)0.0261 (3)
C7D0.61317 (11)0.75954 (7)0.24666 (7)0.0290 (3)
H7DA0.60780.79920.24510.035*
C8D0.59695 (12)0.72870 (7)0.19352 (7)0.0310 (3)
H8DA0.57860.74760.15540.037*
C9D0.63124 (11)0.64288 (6)0.24669 (7)0.0273 (3)
C10D0.65298 (14)0.55395 (8)0.18568 (9)0.0384 (4)
C11D0.67856 (12)0.84395 (7)0.40515 (7)0.0306 (3)
H11D0.68950.82330.44280.037*
C12D0.68713 (12)0.90504 (7)0.40613 (7)0.0293 (3)
C13D0.67608 (13)0.93616 (7)0.35097 (7)0.0325 (3)
H13D0.65910.91760.31250.039*
C14D0.68964 (14)0.99353 (7)0.35203 (8)0.0354 (3)
H14D0.68261.01410.31430.042*
C15D0.71355 (13)1.02134 (7)0.40816 (8)0.0320 (3)
C16D0.72377 (15)0.99121 (7)0.46336 (8)0.0380 (4)
H16D0.73961.01010.50180.046*
C17D0.71078 (15)0.93350 (7)0.46207 (8)0.0360 (3)
H17D0.71810.91310.49990.043*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0433 (2)0.02225 (17)0.01919 (17)−0.00186 (14)0.00250 (13)−0.00207 (12)
S20.0479 (2)0.02552 (18)0.01916 (16)0.00029 (15)0.00072 (14)0.00022 (13)
F1A0.0495 (6)0.0568 (7)0.0428 (6)0.0014 (5)0.0117 (5)−0.0161 (5)
F2A0.0412 (5)0.0452 (6)0.0479 (6)0.0019 (5)−0.0044 (4)−0.0139 (5)
F3A0.0801 (8)0.0306 (5)0.0525 (7)−0.0039 (5)0.0022 (6)−0.0054 (5)
F1B0.0497 (6)0.0661 (8)0.0330 (5)0.0046 (6)−0.0058 (4)−0.0057 (5)
F2B0.0466 (6)0.0562 (7)0.0360 (5)−0.0044 (5)0.0147 (4)−0.0098 (5)
F3B0.0756 (8)0.0424 (6)0.0409 (6)−0.0103 (6)0.0083 (5)−0.0164 (5)
F1C0.0541 (6)0.0421 (6)0.0510 (6)0.0000 (5)−0.0020 (5)−0.0134 (5)
F2C0.0470 (6)0.0404 (6)0.0672 (8)−0.0005 (5)0.0204 (5)−0.0096 (5)
F3C0.0721 (8)0.0244 (5)0.0706 (8)−0.0046 (5)0.0192 (6)0.0002 (5)
F1D0.0662 (7)0.0610 (8)0.0519 (7)−0.0156 (6)0.0271 (6)−0.0221 (6)
F2D0.0589 (6)0.0400 (6)0.0374 (5)0.0005 (5)−0.0047 (5)−0.0104 (5)
F3D0.0794 (8)0.0325 (5)0.0519 (7)0.0123 (6)0.0008 (6)−0.0130 (5)
O1A0.0510 (7)0.0273 (6)0.0309 (6)−0.0041 (5)−0.0018 (5)0.0019 (5)
O1B0.0842 (11)0.0310 (7)0.0724 (11)0.0019 (7)0.0401 (9)−0.0066 (7)
O1C0.0562 (8)0.0296 (6)0.0469 (7)0.0001 (6)0.0101 (6)0.0015 (5)
O1D0.0656 (8)0.0214 (5)0.0350 (6)−0.0019 (5)0.0162 (5)−0.0015 (5)
O110.0501 (7)0.0436 (7)0.0273 (6)0.0008 (6)0.0064 (5)0.0006 (5)
O120.0548 (7)0.0327 (6)0.0216 (5)−0.0055 (5)0.0032 (5)0.0007 (4)
O130.0671 (8)0.0250 (6)0.0303 (6)0.0039 (6)0.0025 (5)−0.0016 (5)
O140.0543 (7)0.0307 (6)0.0307 (6)−0.0084 (5)−0.0015 (5)−0.0027 (5)
O210.0682 (8)0.0303 (6)0.0255 (5)0.0011 (6)−0.0020 (5)0.0060 (5)
O220.0617 (8)0.0409 (7)0.0281 (6)−0.0019 (6)0.0061 (5)0.0095 (5)
O230.0609 (8)0.0509 (8)0.0335 (6)−0.0114 (7)−0.0063 (6)−0.0009 (6)
O240.0616 (8)0.0462 (8)0.0376 (7)0.0118 (7)−0.0007 (6)−0.0127 (6)
O1W0.0702 (9)0.0519 (8)0.0329 (7)−0.0169 (8)0.0026 (6)0.0007 (6)
O2W0.0613 (9)0.0580 (9)0.0371 (7)0.0180 (7)0.0129 (6)−0.0039 (6)
O3W0.0587 (10)0.0836 (13)0.0870 (14)−0.0094 (10)0.0159 (9)−0.0483 (12)
O4W0.0611 (10)0.0841 (15)0.1036 (17)0.0200 (10)0.0237 (10)0.0408 (13)
N1A0.0364 (6)0.0333 (7)0.0225 (6)0.0004 (5)0.0015 (5)−0.0028 (5)
N2A0.0369 (6)0.0275 (6)0.0243 (6)−0.0019 (5)0.0033 (5)0.0022 (5)
N3A0.0374 (6)0.0266 (6)0.0287 (6)−0.0021 (5)0.0033 (5)0.0027 (5)
N1B0.0334 (6)0.0340 (7)0.0200 (6)0.0002 (5)0.0041 (4)−0.0001 (5)
N2B0.0353 (6)0.0252 (6)0.0235 (6)0.0008 (5)0.0042 (5)0.0018 (5)
N3B0.0374 (7)0.0258 (6)0.0272 (6)0.0016 (5)0.0043 (5)−0.0015 (5)
N1C0.0332 (6)0.0267 (6)0.0288 (6)0.0005 (5)0.0045 (5)−0.0029 (5)
N2C0.0369 (6)0.0273 (6)0.0252 (6)0.0021 (5)0.0018 (5)0.0004 (5)
N3C0.0354 (6)0.0272 (6)0.0317 (7)0.0021 (5)0.0033 (5)0.0008 (5)
N1D0.0392 (7)0.0290 (6)0.0244 (6)−0.0031 (5)0.0045 (5)−0.0024 (5)
N2D0.0365 (6)0.0207 (6)0.0270 (6)0.0003 (5)0.0041 (5)0.0007 (5)
N3D0.0361 (6)0.0200 (6)0.0308 (6)−0.0002 (5)0.0042 (5)0.0004 (5)
C1A0.0326 (7)0.0311 (8)0.0328 (8)0.0014 (6)0.0063 (6)−0.0015 (6)
C2A0.0388 (8)0.0294 (7)0.0370 (8)0.0022 (7)0.0063 (6)0.0043 (7)
C3A0.0402 (8)0.0359 (8)0.0284 (7)0.0018 (7)0.0029 (6)0.0064 (6)
C4A0.0330 (7)0.0338 (8)0.0246 (7)0.0010 (6)0.0026 (5)0.0003 (6)
C5A0.0263 (6)0.0295 (7)0.0240 (7)0.0005 (6)0.0038 (5)0.0006 (6)
C6A0.0276 (7)0.0304 (7)0.0244 (7)0.0005 (6)0.0036 (5)0.0014 (6)
C7A0.0380 (8)0.0301 (7)0.0259 (7)0.0012 (6)0.0036 (6)0.0029 (6)
C8A0.0391 (8)0.0373 (8)0.0218 (7)0.0024 (7)0.0028 (5)0.0037 (6)
C9A0.0285 (7)0.0316 (8)0.0260 (7)0.0021 (6)0.0048 (5)−0.0004 (6)
C10A0.0399 (8)0.0321 (8)0.0389 (9)0.0015 (7)0.0059 (7)−0.0047 (7)
C11A0.0423 (8)0.0315 (8)0.0269 (7)−0.0073 (7)0.0029 (6)0.0032 (6)
C12A0.0379 (8)0.0302 (8)0.0280 (7)−0.0058 (6)0.0043 (6)0.0003 (6)
C13A0.0442 (8)0.0315 (8)0.0243 (7)−0.0018 (7)0.0027 (6)−0.0022 (6)
C14A0.0471 (9)0.0327 (8)0.0238 (7)0.0030 (7)0.0034 (6)0.0031 (6)
C15A0.0343 (7)0.0265 (7)0.0294 (7)−0.0009 (6)0.0032 (5)0.0002 (6)
C16A0.0585 (10)0.0357 (9)0.0241 (7)−0.0109 (8)0.0018 (7)−0.0002 (6)
C17A0.0632 (11)0.0371 (9)0.0246 (7)−0.0122 (8)0.0018 (7)0.0043 (7)
C1B0.0293 (7)0.0346 (8)0.0289 (8)0.0007 (6)0.0033 (5)−0.0048 (6)
C2B0.0340 (8)0.0296 (7)0.0375 (8)−0.0007 (6)0.0053 (6)−0.0039 (6)
C3B0.0329 (7)0.0304 (8)0.0348 (8)0.0004 (6)0.0052 (6)0.0048 (6)
C4B0.0294 (7)0.0315 (7)0.0256 (7)−0.0001 (6)0.0047 (5)0.0010 (6)
C5B0.0239 (6)0.0287 (7)0.0238 (7)0.0008 (5)0.0030 (5)0.0008 (6)
C6B0.0245 (6)0.0285 (7)0.0251 (7)0.0021 (5)0.0026 (5)0.0008 (6)
C7B0.0341 (7)0.0273 (7)0.0273 (7)0.0004 (6)0.0043 (5)0.0026 (6)
C8B0.0316 (7)0.0316 (7)0.0262 (7)0.0019 (6)0.0034 (5)0.0065 (6)
C9B0.0238 (6)0.0308 (7)0.0240 (7)0.0006 (5)0.0015 (5)−0.0003 (6)
C10B0.0403 (8)0.0382 (9)0.0323 (8)−0.0021 (7)0.0039 (6)−0.0088 (7)
C11B0.0406 (8)0.0288 (7)0.0246 (7)−0.0009 (6)0.0034 (6)0.0014 (6)
C12B0.0411 (8)0.0283 (7)0.0238 (7)0.0001 (6)0.0026 (6)0.0008 (6)
C13B0.0400 (8)0.0328 (8)0.0249 (7)0.0023 (7)0.0069 (6)0.0037 (6)
C14B0.0426 (8)0.0305 (8)0.0320 (8)0.0009 (7)0.0067 (6)0.0045 (6)
C15B0.0529 (10)0.0298 (8)0.0440 (9)0.0010 (8)0.0155 (8)−0.0049 (7)
C16B0.0717 (13)0.0392 (10)0.0419 (10)−0.0042 (9)0.0294 (9)−0.0043 (8)
C17B0.0637 (11)0.0326 (8)0.0313 (8)−0.0057 (8)0.0173 (8)0.0007 (7)
C1C0.0301 (7)0.0285 (8)0.0404 (9)−0.0013 (6)0.0024 (6)0.0026 (7)
C2C0.0395 (8)0.0297 (8)0.0434 (9)−0.0041 (7)0.0012 (7)0.0088 (7)
C3C0.0422 (9)0.0405 (9)0.0330 (8)−0.0029 (7)0.0028 (6)0.0105 (7)
C4C0.0384 (8)0.0347 (8)0.0284 (7)−0.0005 (7)0.0030 (6)0.0024 (6)
C5C0.0255 (6)0.0282 (7)0.0288 (7)0.0000 (6)0.0013 (5)0.0019 (6)
C6C0.0248 (6)0.0282 (7)0.0284 (7)0.0012 (5)0.0030 (5)0.0007 (6)
C7C0.0300 (7)0.0255 (7)0.0283 (7)−0.0011 (6)0.0030 (5)0.0014 (6)
C8C0.0292 (7)0.0301 (7)0.0261 (7)−0.0015 (6)0.0039 (5)0.0022 (6)
C9C0.0261 (6)0.0275 (7)0.0307 (7)0.0008 (6)0.0028 (5)0.0016 (6)
C10C0.0404 (9)0.0254 (7)0.0516 (10)−0.0023 (7)0.0095 (7)0.0002 (7)
C11C0.0415 (8)0.0319 (8)0.0272 (7)0.0038 (7)0.0007 (6)−0.0019 (6)
C12C0.0379 (8)0.0308 (8)0.0298 (8)0.0027 (6)0.0030 (6)−0.0036 (6)
C13C0.0486 (9)0.0344 (8)0.0274 (7)0.0004 (7)0.0049 (6)−0.0041 (6)
C14C0.0523 (10)0.0374 (9)0.0297 (8)0.0039 (8)0.0043 (7)0.0025 (7)
C15C0.0375 (8)0.0299 (8)0.0386 (8)−0.0002 (7)0.0105 (6)−0.0004 (7)
C16C0.0522 (10)0.0344 (9)0.0414 (9)0.0016 (8)−0.0046 (7)−0.0109 (8)
C17C0.0575 (10)0.0373 (9)0.0315 (8)0.0082 (8)−0.0066 (7)−0.0047 (7)
C1D0.0349 (7)0.0265 (7)0.0326 (8)−0.0029 (6)0.0035 (6)−0.0045 (6)
C2D0.0421 (8)0.0215 (7)0.0423 (9)−0.0004 (6)−0.0003 (7)−0.0015 (7)
C3D0.0447 (8)0.0267 (8)0.0323 (8)−0.0007 (7)−0.0003 (6)0.0050 (6)
C4D0.0357 (7)0.0261 (7)0.0270 (7)−0.0016 (6)0.0027 (5)−0.0004 (6)
C5D0.0273 (6)0.0246 (7)0.0275 (7)−0.0020 (6)0.0047 (5)−0.0008 (6)
C6D0.0264 (6)0.0244 (7)0.0281 (7)−0.0014 (5)0.0054 (5)−0.0002 (6)
C7D0.0331 (7)0.0240 (7)0.0299 (7)0.0000 (6)0.0039 (5)0.0031 (6)
C8D0.0361 (7)0.0310 (8)0.0259 (7)−0.0007 (6)0.0043 (5)0.0039 (6)
C9D0.0287 (7)0.0253 (7)0.0282 (7)−0.0031 (6)0.0042 (5)−0.0012 (6)
C10D0.0473 (9)0.0297 (8)0.0381 (9)−0.0012 (7)0.0052 (7)−0.0086 (7)
C11D0.0412 (8)0.0231 (7)0.0282 (7)0.0018 (6)0.0067 (6)0.0020 (6)
C12D0.0381 (7)0.0221 (7)0.0282 (7)0.0016 (6)0.0060 (6)−0.0008 (6)
C13D0.0476 (9)0.0250 (7)0.0251 (7)0.0030 (6)0.0043 (6)−0.0019 (6)
C14D0.0544 (9)0.0247 (7)0.0280 (7)0.0043 (7)0.0096 (6)0.0034 (6)
C15D0.0415 (8)0.0224 (7)0.0339 (8)0.0023 (6)0.0120 (6)−0.0005 (6)
C16D0.0606 (10)0.0267 (8)0.0268 (7)−0.0016 (7)0.0055 (7)−0.0047 (6)
C17D0.0560 (10)0.0269 (8)0.0248 (7)0.0002 (7)0.0034 (6)0.0025 (6)

Geometric parameters (Å, °)

S1—O121.4750 (11)C14A—H14A0.9500
S1—O111.4767 (13)C15A—C16A1.384 (2)
S1—O141.4782 (13)C16A—C17A1.387 (3)
S1—O131.4808 (13)C16A—H16A0.9500
S2—O241.4636 (14)C17A—H17A0.9500
S2—O231.4786 (15)C1B—C2B1.369 (2)
S2—O211.4794 (13)C1B—C9B1.420 (2)
S2—O221.4838 (13)C1B—C10B1.509 (2)
F1A—C10A1.338 (2)C2B—C3B1.405 (2)
F2A—C10A1.345 (2)C2B—H2BA0.9500
F3A—C10A1.326 (2)C3B—C4B1.374 (2)
F1B—C10B1.339 (2)C3B—H3BA0.9500
F2B—C10B1.337 (2)C4B—C5B1.410 (2)
F3B—C10B1.337 (2)C4B—H4BA0.9500
F1C—C10C1.343 (2)C5B—C9B1.422 (2)
F2C—C10C1.337 (2)C5B—C6B1.452 (2)
F3C—C10C1.329 (2)C6B—C7B1.410 (2)
F1D—C10D1.335 (2)C7B—C8B1.370 (2)
F2D—C10D1.332 (2)C7B—H7BA0.9500
F3D—C10D1.337 (2)C8B—H8BA0.9500
O1A—C15A1.357 (2)C11B—C12B1.465 (2)
O1A—H1A0.8400C11B—H11B0.9500
O1B—C15B1.355 (2)C12B—C13B1.400 (2)
O1B—H1B0.8400C12B—C17B1.400 (2)
O1C—C15C1.357 (2)C13B—C14B1.379 (2)
O1C—H1C0.8400C13B—H13B0.9500
O1D—C15D1.3564 (19)C14B—C15B1.398 (2)
O1D—H1D0.8400C14B—H14B0.9500
O1W—H1W10.810 (17)C15B—C16B1.393 (3)
O1W—H1W20.812 (17)C16B—C17B1.375 (3)
O2W—H2W10.821 (17)C16B—H16B0.9500
O2W—H2W20.828 (17)C17B—H17B0.9500
O3W—H3W10.824 (18)C1C—C2C1.377 (3)
O3W—H3W20.841 (18)C1C—C9C1.421 (2)
O4W—H4W10.835 (18)C1C—C10C1.498 (3)
O4W—H4W20.820 (19)C2C—C3C1.395 (3)
N1A—C8A1.343 (2)C2C—H2CA0.9500
N1A—C9A1.381 (2)C3C—C4C1.373 (3)
N1A—H1AA0.8800C3C—H3CA0.9500
N2A—C6A1.329 (2)C4C—C5C1.421 (2)
N2A—N3A1.3870 (19)C4C—H4CA0.9500
N2A—H2AB0.8800C5C—C9C1.411 (2)
N3A—C11A1.271 (2)C5C—C6C1.448 (2)
N1B—C8B1.340 (2)C6C—C7C1.405 (2)
N1B—C9B1.372 (2)C7C—C8C1.367 (2)
N1B—H1BA0.8800C7C—H7CA0.9500
N2B—C6B1.335 (2)C8C—H8CA0.9500
N2B—N3B1.3938 (18)C11C—C12C1.463 (2)
N2B—H2BB0.8800C11C—H11C0.9500
N3B—C11B1.276 (2)C12C—C17C1.390 (2)
N1C—C8C1.342 (2)C12C—C13C1.399 (2)
N1C—C9C1.376 (2)C13C—C14C1.378 (3)
N1C—H1CA0.8800C13C—H13C0.9500
N2C—C6C1.337 (2)C14C—C15C1.392 (3)
N2C—N3C1.3898 (19)C14C—H14C0.9500
N2C—H2CB0.8800C15C—C16C1.390 (3)
N3C—C11C1.278 (2)C16C—C17C1.385 (3)
N1D—C8D1.347 (2)C16C—H16C0.9500
N1D—C9D1.371 (2)C17C—H17C0.9500
N1D—H1DA0.8800C1D—C2D1.367 (3)
N2D—C6D1.337 (2)C1D—C9D1.428 (2)
N2D—N3D1.3859 (17)C1D—C10D1.506 (2)
N2D—H2DB0.8800C2D—C3D1.397 (3)
N3D—C11D1.271 (2)C2D—H2DA0.9500
C1A—C2A1.375 (2)C3D—C4D1.372 (2)
C1A—C9A1.416 (2)C3D—H3DA0.9500
C1A—C10A1.497 (2)C4D—C5D1.412 (2)
C2A—C3A1.402 (3)C4D—H4DA0.9500
C2A—H2AA0.9500C5D—C9D1.413 (2)
C3A—C4A1.366 (2)C5D—C6D1.449 (2)
C3A—H3AA0.9500C6D—C7D1.410 (2)
C4A—C5A1.416 (2)C7D—C8D1.364 (2)
C4A—H4AA0.9500C7D—H7DA0.9500
C5A—C9A1.409 (2)C8D—H8DA0.9500
C5A—C6A1.446 (2)C11D—C12D1.462 (2)
C6A—C7A1.410 (2)C11D—H11D0.9500
C7A—C8A1.363 (2)C12D—C17D1.395 (2)
C7A—H7AA0.9500C12D—C13D1.402 (2)
C8A—H8AA0.9500C13D—C14D1.381 (2)
C11A—C12A1.458 (2)C13D—H13D0.9500
C11A—H11A0.9500C14D—C15D1.392 (2)
C12A—C17A1.390 (2)C14D—H14D0.9500
C12A—C13A1.395 (2)C15D—C16D1.390 (2)
C13A—C14A1.379 (2)C16D—C17D1.388 (2)
C13A—H13A0.9500C16D—H16D0.9500
C14A—C15A1.398 (2)C17D—H17D0.9500
O12—S1—O11108.99 (8)F3B—C10B—C1B112.13 (16)
O12—S1—O14110.19 (7)F2B—C10B—C1B111.89 (14)
O11—S1—O14110.05 (8)F1B—C10B—C1B112.10 (15)
O12—S1—O13109.70 (7)N3B—C11B—C12B120.67 (15)
O11—S1—O13108.58 (8)N3B—C11B—H11B119.7
O14—S1—O13109.30 (8)C12B—C11B—H11B119.7
O24—S2—O23110.16 (9)C13B—C12B—C17B118.49 (16)
O24—S2—O21110.23 (8)C13B—C12B—C11B123.02 (15)
O23—S2—O21109.45 (9)C17B—C12B—C11B118.46 (15)
O24—S2—O22109.52 (9)C14B—C13B—C12B121.04 (15)
O23—S2—O22109.39 (8)C14B—C13B—H13B119.5
O21—S2—O22108.07 (8)C12B—C13B—H13B119.5
C15A—O1A—H1A109.5C13B—C14B—C15B119.69 (16)
C15B—O1B—H1B109.5C13B—C14B—H14B120.2
C15C—O1C—H1C109.5C15B—C14B—H14B120.2
C15D—O1D—H1D109.5O1B—C15B—C16B118.08 (17)
H1W1—O1W—H1W2109 (3)O1B—C15B—C14B122.24 (18)
H2W1—O2W—H2W2103 (2)C16B—C15B—C14B119.67 (17)
H3W1—O3W—H3W2104 (3)C17B—C16B—C15B120.35 (16)
H4W1—O4W—H4W2104 (3)C17B—C16B—H16B119.8
C8A—N1A—C9A121.06 (14)C15B—C16B—H16B119.8
C8A—N1A—H1AA119.5C16B—C17B—C12B120.71 (17)
C9A—N1A—H1AA119.5C16B—C17B—H17B119.6
C6A—N2A—N3A118.18 (13)C12B—C17B—H17B119.6
C6A—N2A—H2AB120.9C2C—C1C—C9C119.74 (16)
N3A—N2A—H2AB120.9C2C—C1C—C10C119.85 (16)
C11A—N3A—N2A114.69 (13)C9C—C1C—C10C120.38 (16)
C8B—N1B—C9B121.76 (13)C1C—C2C—C3C121.03 (16)
C8B—N1B—H1BA119.1C1C—C2C—H2CA119.5
C9B—N1B—H1BA119.1C3C—C2C—H2CA119.5
C6B—N2B—N3B118.13 (13)C4C—C3C—C2C120.17 (16)
C6B—N2B—H2BB120.9C4C—C3C—H3CA119.9
N3B—N2B—H2BB120.9C2C—C3C—H3CA119.9
C11B—N3B—N2B114.36 (14)C3C—C4C—C5C120.78 (16)
C8C—N1C—C9C121.06 (14)C3C—C4C—H4CA119.6
C8C—N1C—H1CA119.5C5C—C4C—H4CA119.6
C9C—N1C—H1CA119.5C9C—C5C—C4C118.67 (15)
C6C—N2C—N3C118.65 (13)C9C—C5C—C6C118.94 (14)
C6C—N2C—H2CB120.7C4C—C5C—C6C122.24 (15)
N3C—N2C—H2CB120.7N2C—C6C—C7C121.53 (14)
C11C—N3C—N2C115.06 (14)N2C—C6C—C5C120.55 (14)
C8D—N1D—C9D121.28 (14)C7C—C6C—C5C117.90 (14)
C8D—N1D—H1DA119.4C8C—C7C—C6C119.59 (14)
C9D—N1D—H1DA119.4C8C—C7C—H7CA120.2
C6D—N2D—N3D117.71 (13)C6C—C7C—H7CA120.2
C6D—N2D—H2DB121.1N1C—C8C—C7C122.68 (14)
N3D—N2D—H2DB121.1N1C—C8C—H8CA118.7
C11D—N3D—N2D115.80 (13)C7C—C8C—H8CA118.7
C2A—C1A—C9A120.45 (15)N1C—C9C—C5C119.35 (14)
C2A—C1A—C10A119.84 (16)N1C—C9C—C1C121.05 (15)
C9A—C1A—C10A119.70 (15)C5C—C9C—C1C119.57 (15)
C1A—C2A—C3A120.19 (16)F3C—C10C—F2C107.13 (15)
C1A—C2A—H2AA119.9F3C—C10C—F1C106.28 (15)
C3A—C2A—H2AA119.9F2C—C10C—F1C105.80 (16)
C4A—C3A—C2A120.50 (15)F3C—C10C—C1C112.48 (16)
C4A—C3A—H3AA119.8F2C—C10C—C1C112.50 (15)
C2A—C3A—H3AA119.8F1C—C10C—C1C112.18 (15)
C3A—C4A—C5A120.54 (15)N3C—C11C—C12C121.87 (15)
C3A—C4A—H4AA119.7N3C—C11C—H11C119.1
C5A—C4A—H4AA119.7C12C—C11C—H11C119.1
C9A—C5A—C4A119.19 (15)C17C—C12C—C13C118.11 (17)
C9A—C5A—C6A118.83 (14)C17C—C12C—C11C119.13 (16)
C4A—C5A—C6A121.98 (14)C13C—C12C—C11C122.75 (15)
N2A—C6A—C7A121.25 (15)C14C—C13C—C12C120.75 (16)
N2A—C6A—C5A120.74 (14)C14C—C13C—H13C119.6
C7A—C6A—C5A118.01 (14)C12C—C13C—H13C119.6
C8A—C7A—C6A119.85 (15)C13C—C14C—C15C120.54 (17)
C8A—C7A—H7AA120.1C13C—C14C—H14C119.7
C6A—C7A—H7AA120.1C15C—C14C—H14C119.7
N1A—C8A—C7A122.55 (15)O1C—C15C—C16C122.71 (17)
N1A—C8A—H8AA118.7O1C—C15C—C14C117.90 (17)
C7A—C8A—H8AA118.7C16C—C15C—C14C119.39 (17)
N1A—C9A—C5A119.55 (15)C17C—C16C—C15C119.66 (17)
N1A—C9A—C1A121.49 (15)C17C—C16C—H16C120.2
C5A—C9A—C1A118.96 (14)C15C—C16C—H16C120.2
F3A—C10A—F1A107.99 (15)C16C—C17C—C12C121.54 (17)
F3A—C10A—F2A106.30 (15)C16C—C17C—H17C119.2
F1A—C10A—F2A106.34 (15)C12C—C17C—H17C119.2
F3A—C10A—C1A112.91 (15)C2D—C1D—C9D120.07 (15)
F1A—C10A—C1A112.11 (15)C2D—C1D—C10D120.03 (15)
F2A—C10A—C1A110.80 (14)C9D—C1D—C10D119.68 (15)
N3A—C11A—C12A121.08 (15)C1D—C2D—C3D120.98 (15)
N3A—C11A—H11A119.5C1D—C2D—H2DA119.5
C12A—C11A—H11A119.5C3D—C2D—H2DA119.5
C17A—C12A—C13A118.46 (16)C4D—C3D—C2D120.11 (15)
C17A—C12A—C11A118.37 (15)C4D—C3D—H3DA119.9
C13A—C12A—C11A123.12 (15)C2D—C3D—H3DA119.9
C14A—C13A—C12A120.05 (15)C3D—C4D—C5D120.67 (15)
C14A—C13A—H13A120.0C3D—C4D—H4DA119.7
C12A—C13A—H13A120.0C5D—C4D—H4DA119.7
C13A—C14A—C15A120.76 (15)C4D—C5D—C9D119.23 (14)
C13A—C14A—H14A119.6C4D—C5D—C6D122.20 (14)
C15A—C14A—H14A119.6C9D—C5D—C6D118.56 (14)
O1A—C15A—C16A122.69 (15)N2D—C6D—C7D121.76 (14)
O1A—C15A—C14A117.67 (14)N2D—C6D—C5D119.98 (14)
C16A—C15A—C14A119.61 (16)C7D—C6D—C5D118.25 (14)
C15A—C16A—C17A119.03 (16)C8D—C7D—C6D119.49 (15)
C15A—C16A—H16A120.5C8D—C7D—H7DA120.3
C17A—C16A—H16A120.5C6D—C7D—H7DA120.3
C16A—C17A—C12A121.83 (16)N1D—C8D—C7D122.62 (15)
C16A—C17A—H17A119.1N1D—C8D—H8DA118.7
C12A—C17A—H17A119.1C7D—C8D—H8DA118.7
C2B—C1B—C9B120.26 (15)N1D—C9D—C5D119.54 (14)
C2B—C1B—C10B120.03 (16)N1D—C9D—C1D121.78 (14)
C9B—C1B—C10B119.71 (15)C5D—C9D—C1D118.67 (14)
C1B—C2B—C3B121.04 (16)F2D—C10D—F1D106.48 (16)
C1B—C2B—H2BA119.5F2D—C10D—F3D106.44 (15)
C3B—C2B—H2BA119.5F1D—C10D—F3D107.05 (16)
C4B—C3B—C2B119.78 (15)F2D—C10D—C1D113.44 (15)
C4B—C3B—H3BA120.1F1D—C10D—C1D111.08 (14)
C2B—C3B—H3BA120.1F3D—C10D—C1D111.95 (16)
C3B—C4B—C5B120.95 (14)N3D—C11D—C12D119.94 (14)
C3B—C4B—H4BA119.5N3D—C11D—H11D120.0
C5B—C4B—H4BA119.5C12D—C11D—H11D120.0
C4B—C5B—C9B119.12 (14)C17D—C12D—C13D118.45 (15)
C4B—C5B—C6B122.54 (14)C17D—C12D—C11D120.48 (14)
C9B—C5B—C6B118.31 (14)C13D—C12D—C11D121.02 (14)
N2B—C6B—C7B120.89 (14)C14D—C13D—C12D120.69 (15)
N2B—C6B—C5B120.79 (14)C14D—C13D—H13D119.7
C7B—C6B—C5B118.29 (14)C12D—C13D—H13D119.7
C8B—C7B—C6B119.77 (15)C13D—C14D—C15D120.25 (15)
C8B—C7B—H7BA120.1C13D—C14D—H14D119.9
C6B—C7B—H7BA120.1C15D—C14D—H14D119.9
N1B—C8B—C7B122.33 (15)O1D—C15D—C16D122.39 (15)
N1B—C8B—H8BA118.8O1D—C15D—C14D117.78 (15)
C7B—C8B—H8BA118.8C16D—C15D—C14D119.82 (15)
N1B—C9B—C1B121.65 (14)C17D—C16D—C15D119.76 (16)
N1B—C9B—C5B119.50 (14)C17D—C16D—H16D120.1
C1B—C9B—C5B118.84 (14)C15D—C16D—H16D120.1
F3B—C10B—F2B107.05 (15)C16D—C17D—C12D121.03 (15)
F3B—C10B—F1B107.03 (15)C16D—C17D—H17D119.5
F2B—C10B—F1B106.26 (16)C12D—C17D—H17D119.5
C6A—N2A—N3A—C11A174.68 (15)C13B—C12B—C17B—C16B−1.8 (3)
C6B—N2B—N3B—C11B−166.53 (14)C11B—C12B—C17B—C16B176.22 (19)
C6C—N2C—N3C—C11C175.23 (15)C9C—C1C—C2C—C3C0.1 (3)
C6D—N2D—N3D—C11D−177.70 (14)C10C—C1C—C2C—C3C177.96 (16)
C9A—C1A—C2A—C3A2.4 (2)C1C—C2C—C3C—C4C1.5 (3)
C10A—C1A—C2A—C3A−176.03 (16)C2C—C3C—C4C—C5C−1.4 (3)
C1A—C2A—C3A—C4A1.4 (3)C3C—C4C—C5C—C9C−0.2 (2)
C2A—C3A—C4A—C5A−3.0 (2)C3C—C4C—C5C—C6C−175.78 (15)
C3A—C4A—C5A—C9A0.7 (2)N3C—N2C—C6C—C7C−8.9 (2)
C3A—C4A—C5A—C6A−178.49 (15)N3C—N2C—C6C—C5C169.30 (13)
N3A—N2A—C6A—C7A−3.0 (2)C9C—C5C—C6C—N2C176.53 (14)
N3A—N2A—C6A—C5A177.14 (13)C4C—C5C—C6C—N2C−7.9 (2)
C9A—C5A—C6A—N2A175.32 (13)C9C—C5C—C6C—C7C−5.2 (2)
C4A—C5A—C6A—N2A−5.5 (2)C4C—C5C—C6C—C7C170.37 (14)
C9A—C5A—C6A—C7A−4.6 (2)N2C—C6C—C7C—C8C−174.45 (14)
C4A—C5A—C6A—C7A174.61 (14)C5C—C6C—C7C—C8C7.3 (2)
N2A—C6A—C7A—C8A−176.70 (15)C9C—N1C—C8C—C7C−2.9 (2)
C5A—C6A—C7A—C8A3.2 (2)C6C—C7C—C8C—N1C−3.4 (2)
C9A—N1A—C8A—C7A−2.0 (2)C8C—N1C—C9C—C5C5.0 (2)
C6A—C7A—C8A—N1A0.1 (3)C8C—N1C—C9C—C1C−173.31 (14)
C8A—N1A—C9A—C5A0.5 (2)C4C—C5C—C9C—N1C−176.54 (14)
C8A—N1A—C9A—C1A−178.97 (15)C6C—C5C—C9C—N1C−0.8 (2)
C4A—C5A—C9A—N1A−176.41 (13)C4C—C5C—C9C—C1C1.8 (2)
C6A—C5A—C9A—N1A2.8 (2)C6C—C5C—C9C—C1C177.50 (13)
C4A—C5A—C9A—C1A3.1 (2)C2C—C1C—C9C—N1C176.53 (15)
C6A—C5A—C9A—C1A−177.73 (13)C10C—C1C—C9C—N1C−1.3 (2)
C2A—C1A—C9A—N1A174.83 (15)C2C—C1C—C9C—C5C−1.7 (2)
C10A—C1A—C9A—N1A−6.7 (2)C10C—C1C—C9C—C5C−179.57 (15)
C2A—C1A—C9A—C5A−4.6 (2)C2C—C1C—C10C—F3C−1.2 (2)
C10A—C1A—C9A—C5A173.83 (14)C9C—C1C—C10C—F3C176.61 (15)
C2A—C1A—C10A—F3A7.6 (2)C2C—C1C—C10C—F2C119.88 (18)
C9A—C1A—C10A—F3A−170.92 (15)C9C—C1C—C10C—F2C−62.3 (2)
C2A—C1A—C10A—F1A−114.69 (18)C2C—C1C—C10C—F1C−120.97 (18)
C9A—C1A—C10A—F1A66.8 (2)C9C—C1C—C10C—F1C56.9 (2)
C2A—C1A—C10A—F2A126.68 (17)N2C—N3C—C11C—C12C175.75 (14)
C9A—C1A—C10A—F2A−51.8 (2)N3C—C11C—C12C—C17C172.15 (17)
N2A—N3A—C11A—C12A178.14 (14)N3C—C11C—C12C—C13C−9.1 (3)
N3A—C11A—C12A—C17A−171.37 (17)C17C—C12C—C13C—C14C−1.3 (3)
N3A—C11A—C12A—C13A6.0 (3)C11C—C12C—C13C—C14C179.97 (17)
C17A—C12A—C13A—C14A3.8 (3)C12C—C13C—C14C—C15C0.3 (3)
C11A—C12A—C13A—C14A−173.53 (17)C13C—C14C—C15C—O1C−179.77 (16)
C12A—C13A—C14A—C15A0.7 (3)C13C—C14C—C15C—C16C0.9 (3)
C13A—C14A—C15A—O1A177.59 (16)O1C—C15C—C16C—C17C179.70 (18)
C13A—C14A—C15A—C16A−4.1 (3)C14C—C15C—C16C—C17C−1.0 (3)
O1A—C15A—C16A—C17A−179.04 (17)C15C—C16C—C17C—C12C0.0 (3)
C14A—C15A—C16A—C17A2.7 (3)C13C—C12C—C17C—C16C1.2 (3)
C15A—C16A—C17A—C12A1.9 (3)C11C—C12C—C17C—C16C179.97 (18)
C13A—C12A—C17A—C16A−5.2 (3)C9D—C1D—C2D—C3D−1.4 (3)
C11A—C12A—C17A—C16A172.26 (18)C10D—C1D—C2D—C3D173.24 (16)
C9B—C1B—C2B—C3B0.6 (2)C1D—C2D—C3D—C4D−2.5 (3)
C10B—C1B—C2B—C3B−179.37 (15)C2D—C3D—C4D—C5D2.3 (3)
C1B—C2B—C3B—C4B−0.7 (2)C3D—C4D—C5D—C9D1.7 (2)
C2B—C3B—C4B—C5B−0.1 (2)C3D—C4D—C5D—C6D−176.80 (15)
C3B—C4B—C5B—C9B1.0 (2)N3D—N2D—C6D—C7D−2.7 (2)
C3B—C4B—C5B—C6B−176.94 (14)N3D—N2D—C6D—C5D176.75 (12)
N3B—N2B—C6B—C7B−5.8 (2)C4D—C5D—C6D—N2D4.2 (2)
N3B—N2B—C6B—C5B172.22 (13)C9D—C5D—C6D—N2D−174.39 (13)
C4B—C5B—C6B—N2B1.6 (2)C4D—C5D—C6D—C7D−176.38 (14)
C9B—C5B—C6B—N2B−176.40 (13)C9D—C5D—C6D—C7D5.1 (2)
C4B—C5B—C6B—C7B179.70 (14)N2D—C6D—C7D—C8D178.09 (14)
C9B—C5B—C6B—C7B1.7 (2)C5D—C6D—C7D—C8D−1.4 (2)
N2B—C6B—C7B—C8B177.71 (14)C9D—N1D—C8D—C7D0.7 (2)
C5B—C6B—C7B—C8B−0.4 (2)C6D—C7D—C8D—N1D−1.6 (2)
C9B—N1B—C8B—C7B0.4 (2)C8D—N1D—C9D—C5D3.2 (2)
C6B—C7B—C8B—N1B−0.7 (2)C8D—N1D—C9D—C1D−175.89 (14)
C8B—N1B—C9B—C1B−177.93 (14)C4D—C5D—C9D—N1D175.41 (14)
C8B—N1B—C9B—C5B1.0 (2)C6D—C5D—C9D—N1D−6.0 (2)
C2B—C1B—C9B—N1B179.26 (14)C4D—C5D—C9D—C1D−5.5 (2)
C10B—C1B—C9B—N1B−0.8 (2)C6D—C5D—C9D—C1D173.12 (13)
C2B—C1B—C9B—C5B0.3 (2)C2D—C1D—C9D—N1D−175.57 (15)
C10B—C1B—C9B—C5B−179.72 (14)C10D—C1D—C9D—N1D9.8 (2)
C4B—C5B—C9B—N1B179.91 (13)C2D—C1D—C9D—C5D5.3 (2)
C6B—C5B—C9B—N1B−2.0 (2)C10D—C1D—C9D—C5D−169.30 (14)
C4B—C5B—C9B—C1B−1.1 (2)C2D—C1D—C10D—F2D122.03 (18)
C6B—C5B—C9B—C1B176.96 (13)C9D—C1D—C10D—F2D−63.3 (2)
C2B—C1B—C10B—F3B−1.7 (2)C2D—C1D—C10D—F1D−118.07 (19)
C9B—C1B—C10B—F3B178.35 (14)C9D—C1D—C10D—F1D56.6 (2)
C2B—C1B—C10B—F2B118.63 (18)C2D—C1D—C10D—F3D1.5 (2)
C9B—C1B—C10B—F2B−61.3 (2)C9D—C1D—C10D—F3D176.19 (15)
C2B—C1B—C10B—F1B−122.11 (18)N2D—N3D—C11D—C12D175.34 (13)
C9B—C1B—C10B—F1B57.9 (2)N3D—C11D—C12D—C17D179.64 (16)
N2B—N3B—C11B—C12B175.40 (14)N3D—C11D—C12D—C13D−3.1 (2)
N3B—C11B—C12B—C13B15.0 (3)C17D—C12D—C13D—C14D0.9 (3)
N3B—C11B—C12B—C17B−162.93 (18)C11D—C12D—C13D—C14D−176.46 (16)
C17B—C12B—C13B—C14B−0.1 (3)C12D—C13D—C14D—C15D−0.7 (3)
C11B—C12B—C13B—C14B−178.04 (16)C13D—C14D—C15D—O1D179.32 (16)
C12B—C13B—C14B—C15B2.0 (3)C13D—C14D—C15D—C16D0.0 (3)
C13B—C14B—C15B—O1B179.48 (19)O1D—C15D—C16D—C17D−178.83 (17)
C13B—C14B—C15B—C16B−2.0 (3)C14D—C15D—C16D—C17D0.5 (3)
O1B—C15B—C16B—C17B178.7 (2)C15D—C16D—C17D—C12D−0.3 (3)
C14B—C15B—C16B—C17B0.1 (3)C13D—C12D—C17D—C16D−0.4 (3)
C15B—C16B—C17B—C12B1.8 (4)C11D—C12D—C17D—C16D176.94 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4W—H4W1···O11i0.835 (18)2.23 (3)2.986 (2)151 (5)
N2A—H2AB···O11i0.881.992.8592 (18)170
C4A—H4AA···O11i0.952.283.199 (2)163
O1A—H1A···O12ii0.841.892.6677 (18)154
O1D—H1D···O13ii0.841.752.5771 (17)167
O4W—H4W2···O14iii0.820 (19)2.06 (2)2.860 (2)167 (5)
C4D—H4DA···O14iii0.952.503.367 (2)152
C11D—H11D···O14iii0.952.523.272 (2)136
N1A—H1AA···O21i0.882.062.8636 (18)151
O3W—H3W2···O22i0.841 (18)2.039 (19)2.864 (2)167 (4)
N2B—H2BB···O22iv0.881.932.7909 (18)166
C4B—H4BA···O22iv0.952.373.294 (2)165
C11B—H11B···O22iv0.952.553.319 (2)138
O3W—H3W1···O23iii0.824 (18)1.952 (19)2.776 (2)179 (5)
O1W—H1W1···O24iii0.810 (17)1.933 (17)2.725 (2)165 (3)
C8A—H8AA···O24i0.952.393.134 (2)135
C7C—H7CA···O1Av0.952.463.0647 (19)122
C8C—H8CA···O1Av0.952.473.078 (2)122
O2W—H2W1···O1Dvi0.821 (17)2.114 (18)2.933 (2)175 (4)
C8B—H8BA···O1Dv0.952.343.234 (2)157
O1C—H1C···O3Wv0.841.822.651 (2)168
O2W—H2W2···O4Wi0.828 (17)1.931 (17)2.759 (3)177 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+3/2, y+1/2, −z+1; (iv) x, y, z−1; (v) x, y−1, z; (vi) x−1/2, −y+3/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2084).

References

  • Chen, Y. L., Fang, K. C., Sheu, J. Y., Hsu, S. L. & Tzeng, C. C. (2001). J. Med. Chem.44, 2374–2377. [PubMed]
  • Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83–90.
  • El-Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429–1438.
  • Fun, H.-K., Chinnakali, K., Razak, I. A., Lu, Z.-L. & Kang, B.-S. (1999). Acta Cryst. C55, 574–576.
  • Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem.13, 768–770. [PubMed]
  • Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185.
  • Maguire, M. P., Sheets, K. R., McVety, K., Spada, A. P. & Zilberstein, A. (1994). J. Med. Chem.37, 2129–2137. [PubMed]
  • Misra, V. S., Singh, S., Agarwal, R. & Chaudhary, K. C. (1981). J. Chem. Soc. Pak.3, 209–213.
  • Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Versions 1.171.31.8. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Pandey, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Il Farmaco, 54, 624–628. [PubMed]
  • Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem.35, 1021–1035. [PubMed]
  • Sadık, G., Necmi, D., Ibrahim, Y., Alaaddin, Ç. & Dinçer, M. (2004). Acta Cryst. E60, o889–o891.
  • Saim, O., Dincer, U., Leyla, T. Y., Nermin, B. & Bahattin, G. (2004). J. Mol. Struct.688, 207–211.
  • Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33–37.
  • Varma, R. S., Prakash, R., Khan, M. M. & Ali, A. (1986). Indian Drugs, 23, 345–349.
  • Wang, Z., Jian, F., Duan, C., Bai, Z. & You, X. (1998). Acta Cryst. C54, 1927–1929.
  • Yathirajan, H. S., Sarojini, B. K., Narayana, B., Sunil, K. & Bolte, M. (2007). Acta Cryst. E63, o2720–o2721.
  • Zhang, X. & Jenekhe, S. A. (2000). Macromolecules, 33, 2069–2082.

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