organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Pages o2619-o2620

N-(1,3-Dioxo-2,3-di­hydro-1H-isoindol-2-yl)-4,4′′-di­fluoro-5′-hy­dr­oxy-1,1′:3′,1′′-terphenyl-4′-carboxamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu, PO, Mangalore 574 153, India
*Correspondence e-mail: hkfun@usm.my

(Received 21 July 2012; accepted 26 July 2012; online 1 August 2012)

The asymmetric unit of the title compound, C27H16F2N2O4, consists of two crystallographically independent mol­ecules (A and B). In mol­ecule B, the isoindoline-1,3-dione ring system is disordered over two set of sites with a site-occupancy ratio of 0.658 (12):0.342 (12). In mol­ecule A, the fluoro-substituted benzene rings make dihedral angles of 18.36 (8) and 46.37 (8)° with the central benzene ring, whereas the corresponding angles are 40.90 (8) and 52.89 (9)° in mol­ecule B. The isoindoline ring system in mol­ecule A and the major and minor components of the disordered isoindoline ring system in mol­ecule B make dihedral angles of 58.50 (4), 54.13 (16) and 70.01 (28) °, respectively, with their attached benzene rings, linked through the amide group. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring in each mol­ecule. In the crystal, mol­ecules are linked by N—H⋯O, C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. The crystal studied was a non-merohedral twin with a refined twin component ratio of 0.9316 (8):0.0684 (8).

Related literature

For related structures and background to terphenyls and their oxadiazole derivatives, see: Fun et al. (2012a[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o163.],b[Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o674-o675.]); Samshuddin et al. (2011)[Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, 2011, M745.]. For the planarity of isoindoline, see: Asad et al. (2011[Asad, M., Oo, C.-W., Osman, H., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o1712.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C27H16F2N2O4

  • Mr = 470.42

  • Monoclinic, P 21 /c

  • a = 24.8732 (10) Å

  • b = 8.9875 (4) Å

  • c = 21.3722 (9) Å

  • β = 114.921 (1)°

  • V = 4332.9 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.41 × 0.31 × 0.14 mm

Data collection
  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.956, Tmax = 0.985

  • 16713 measured reflections

  • 16713 independent reflections

  • 12698 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.168

  • S = 1.05

  • 16713 reflections

  • 748 parameters

  • 45 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.90 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1NA⋯O2Ai 0.80 (3) 2.02 (3) 2.8000 (19) 166 (3)
O1B—H1OB⋯O2B 0.88 (3) 1.79 (4) 2.5663 (17) 145 (4)
N1B—H1NB⋯O2Bii 0.91 (3) 2.04 (3) 2.779 (2) 138 (2)
O1A—H1OA⋯O2A 0.82 (3) 1.94 (3) 2.6402 (18) 143 (3)
C2A—H2AA⋯F2Aiii 0.93 2.45 3.160 (2) 133
C4B—H4BA⋯O3Biv 0.93 2.41 3.271 (7) 154
C14B—H14B⋯O3Bv 0.93 2.44 3.293 (6) 152
C25B—H25B⋯O1Bvi 0.93 2.47 3.209 (3) 136
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) -x, -y+2, -z; (v) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In continuation of our work on synthesis of various terphenyl derivatives (Fun et al., 2012a,b), the title compound was prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Samshuddin et al., 2011).

The asymmetric unit of the title compound consists of two crystallographically independent molecules (A and B) as shown in Fig. 1. Each molecule contains one benzene ring [C7–C12], two fluoro-substituted benzene rings [C1–C6 & C13–C18] and an isoindoline-1,3-dione ring system [N2/O3/O4/C20–C27]. In molecule B, isoindoline-1,3-dione ring system is disordered over two positions with a site-occupancy ratio of 0.658 (12):0.342 (12). In molecule A, the fluoro-substituted benzene rings make dihedral angles of 18.36 (8) and 46.37 (8)° with the C7–C12 benzene ring, whereas the corresponding angles are 40.90 (8) and 52.89 (9)° in molecule B. The isoindoline ring systems [N2A/C20A–C27A, N2B/C20B–C27B & N2X/C20X–C27X; maximum deviations = 0.035 (1), 0.075 (4) and 0.084 (18) Å, respectively] make dihedral angles of 58.50 (4), 54.13 (16) and 70.01 (28) °, respectively with their attached C7–C12 benzene ring. An intramolecular O—H···O hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1; Bernstein et al., 1995) in each molecule. The bond lengths and angles are comparable to those found in related structures (Fun et al., 2012a,b)

In the crystal (Fig. 2), molecules are linked by N1A—H1NA···O2A, N1B—H1NB···O2B, C2A—H2AA···F2A, C4B—H4BA···O3B, C14B—H14B···O3B and C25B—H25B···O1B hydrogen bonds into sheets parallel to bc plane.

Related literature top

For related structures and background to terphenyls and their oxadiazole derivatives, see: Fun et al. (2012a,b); Samshuddin et al. (2011). For the planarity of isoindoline, see: Asad et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 4,4''-difluoro-5'-hydroxy-1,1':3',1''-terphenyl-4'-carbohydrazide (3.40 g, 0.01 mol) and phthalic anhydride (1.48 g, 0.01 mol) was dissolved in acetic acid (25 ml) and heated to reflux for 6 h. The reaction mixture was then poured into ice cold water, filtered and crystallized from ethanol. Colourless blocks were grown from DMF solution by slow evaporation method and yield of the compound was 76%. (m.p. 506 K).

Refinement top

N-bound and O-bound H atoms were located in a difference fourier map and refined freely [N1A—H1NA = 0.80 (3) Å, N1B—H1NB = 0.91 (3) Å, O1A—H1OA = 0.82 (3) Å, O1B—H1OB = 0.88 (3) Å]. The remaining H atoms were positioned geometrically [C—H = 0.93 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C). FLAT restraint was applied to the N2/O3/O4/C20–C27 ring system in molecule A and minor component of molecule B so that the planarity of isoindoline ring is agreed with that found in a related structure (Asad et al., 2011). Ten outliers, (0 2 3), (1 0 0), (3 3 5), (20 0 6), (12 0 6), (21 3 6), (10 1 7), (15 6 6), (7 4 6) and (14 5 6), were omitted in the final refinement. The crystal studied was a non-merohedral twin with BASF = 0.0684 (8).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. Intramolecular hydrogen bonds are shown by dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.
N-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)-4,4''-difluoro- 5'-hydroxy-1,1':3',1''-terphenyl-4'-carboxamide top
Crystal data top
C27H16F2N2O4F(000) = 1936
Mr = 470.42Dx = 1.442 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9881 reflections
a = 24.8732 (10) Åθ = 2.8–33.2°
b = 8.9875 (4) ŵ = 0.11 mm1
c = 21.3722 (9) ÅT = 100 K
β = 114.921 (1)°Block, colourless
V = 4332.9 (3) Å30.41 × 0.31 × 0.14 mm
Z = 8
Data collection top
Bruker APEX DUO CCD
diffractometer
16713 independent reflections
Radiation source: fine-focus sealed tube12698 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
ϕ and ω scansθmax = 33.3°, θmin = 0.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3834
Tmin = 0.956, Tmax = 0.985k = 1313
16713 measured reflectionsl = 032
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0737P)2 + 2.8746P]
where P = (Fo2 + 2Fc2)/3
16713 reflections(Δ/σ)max < 0.001
748 parametersΔρmax = 0.63 e Å3
45 restraintsΔρmin = 0.90 e Å3
Crystal data top
C27H16F2N2O4V = 4332.9 (3) Å3
Mr = 470.42Z = 8
Monoclinic, P21/cMo Kα radiation
a = 24.8732 (10) ŵ = 0.11 mm1
b = 8.9875 (4) ÅT = 100 K
c = 21.3722 (9) Å0.41 × 0.31 × 0.14 mm
β = 114.921 (1)°
Data collection top
Bruker APEX DUO CCD
diffractometer
16713 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
12698 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.985Rint = 0.000
16713 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05645 restraints
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.63 e Å3
16713 reflectionsΔρmin = 0.90 e Å3
748 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.70185 (5)0.57672 (16)0.07644 (6)0.0364 (3)
F2A0.74047 (5)0.31572 (16)0.47234 (7)0.0448 (3)
O1A0.44381 (5)0.67527 (14)0.09291 (6)0.0239 (2)
O2A0.45373 (5)0.64374 (13)0.22015 (7)0.0244 (2)
O3A0.37372 (5)0.32205 (15)0.22722 (7)0.0272 (2)
O4A0.52736 (6)0.57608 (18)0.39267 (8)0.0384 (3)
N1A0.49213 (6)0.42265 (15)0.26521 (7)0.0194 (2)
N2A0.46069 (6)0.43104 (14)0.30464 (7)0.0200 (2)
C1A0.66264 (7)0.46269 (19)0.06103 (8)0.0220 (3)
H1AA0.67520.39570.09760.026*
C2A0.69280 (7)0.4694 (2)0.01934 (9)0.0255 (3)
H2AA0.72550.40910.02780.031*
C3A0.67274 (7)0.5687 (2)0.03518 (9)0.0258 (3)
C4A0.62450 (7)0.6598 (2)0.04955 (9)0.0262 (3)
H4AA0.61160.72400.08720.031*
C5A0.59568 (7)0.65329 (19)0.00633 (9)0.0233 (3)
H5AA0.56370.71600.01460.028*
C6A0.61381 (7)0.55424 (17)0.04938 (8)0.0193 (3)
C7A0.58244 (6)0.54752 (17)0.09474 (8)0.0185 (2)
C8A0.52569 (6)0.60577 (17)0.07381 (8)0.0194 (3)
H8AA0.50620.64420.02950.023*
C9A0.49761 (6)0.60762 (17)0.11803 (8)0.0187 (3)
C10A0.52419 (6)0.54063 (16)0.18387 (8)0.0177 (2)
C11A0.58238 (6)0.48200 (16)0.20595 (8)0.0177 (2)
C12A0.61013 (6)0.48774 (17)0.16141 (8)0.0186 (3)
H12A0.64840.45060.17640.022*
C13A0.61965 (6)0.42961 (17)0.27708 (8)0.0190 (3)
C14A0.62408 (7)0.51251 (19)0.33414 (8)0.0215 (3)
H14A0.59990.59520.32790.026*
C15A0.66434 (7)0.4728 (2)0.40044 (9)0.0270 (3)
H15A0.66730.52780.43860.032*
C16A0.69952 (8)0.3503 (2)0.40793 (10)0.0319 (4)
C17A0.69626 (8)0.2637 (2)0.35338 (11)0.0319 (4)
H17A0.72040.18060.36040.038*
C18A0.65589 (7)0.30408 (19)0.28748 (10)0.0254 (3)
H18A0.65290.24710.24980.030*
C19A0.48859 (6)0.54052 (16)0.22477 (8)0.0188 (3)
C20A0.40094 (6)0.38583 (17)0.28064 (8)0.0192 (3)
C21A0.38250 (7)0.43651 (17)0.33479 (8)0.0199 (3)
C22A0.32915 (7)0.4177 (2)0.33958 (9)0.0266 (3)
H22A0.29820.36410.30660.032*
C23A0.32378 (8)0.4828 (2)0.39620 (10)0.0297 (3)
H23A0.28850.47220.40090.036*
C24A0.36994 (9)0.5627 (2)0.44533 (10)0.0308 (4)
H24A0.36490.60580.48200.037*
C25A0.42400 (9)0.5795 (2)0.44060 (10)0.0305 (4)
H25A0.45530.63150.47390.037*
C26A0.42891 (7)0.51557 (19)0.38443 (9)0.0228 (3)
C27A0.47978 (7)0.51708 (19)0.36511 (9)0.0243 (3)
F1B0.24301 (5)0.91133 (16)0.29187 (5)0.0347 (3)
F2B0.22044 (6)1.19023 (17)0.26237 (7)0.0440 (3)
O1B0.02966 (5)0.75887 (17)0.11463 (6)0.0279 (3)
O2B0.03502 (6)0.78615 (14)0.23665 (6)0.0256 (2)
N1B0.00874 (7)0.98785 (17)0.25626 (7)0.0249 (3)
C1B0.20753 (7)0.87878 (19)0.11017 (8)0.0210 (3)
H1BA0.22630.85840.08160.025*
C2B0.24027 (7)0.8785 (2)0.18146 (8)0.0239 (3)
H2BA0.28060.85750.20100.029*
C3B0.21122 (7)0.9102 (2)0.22228 (8)0.0242 (3)
C4B0.15137 (7)0.9400 (2)0.19595 (8)0.0270 (3)
H4BA0.13310.96040.22500.032*
C5B0.11913 (7)0.9385 (2)0.12468 (8)0.0245 (3)
H5BA0.07860.95720.10580.029*
C6B0.14672 (6)0.90931 (18)0.08102 (7)0.0189 (3)
C7B0.11148 (6)0.90581 (18)0.00535 (7)0.0192 (3)
C8B0.05588 (7)0.8402 (2)0.02207 (8)0.0222 (3)
H8BA0.04030.80240.00730.027*
C9B0.02312 (6)0.83030 (19)0.09311 (8)0.0204 (3)
C10B0.04459 (7)0.89221 (17)0.13910 (7)0.0180 (2)
C11B0.10190 (7)0.95784 (17)0.11118 (7)0.0184 (2)
C12B0.13399 (7)0.96299 (18)0.03979 (8)0.0196 (3)
H12B0.17151.00570.02150.023*
C13B0.13197 (7)1.01929 (18)0.15303 (8)0.0204 (3)
C14B0.13921 (8)0.9340 (2)0.20379 (9)0.0255 (3)
H14B0.12410.83780.21280.031*
C15B0.16887 (9)0.9922 (2)0.24094 (10)0.0309 (4)
H15B0.17360.93590.27480.037*
C16B0.19113 (8)1.1348 (2)0.22641 (10)0.0306 (4)
C17B0.18557 (8)1.2222 (2)0.17653 (9)0.0289 (3)
H17B0.20121.31790.16770.035*
C18B0.15578 (7)1.16279 (19)0.13971 (9)0.0237 (3)
H18B0.15171.21970.10560.028*
C19B0.00406 (7)0.88355 (17)0.21341 (8)0.0202 (3)
O3B0.1114 (3)1.0874 (6)0.3230 (3)0.0205 (7)0.658 (12)
O4B0.03851 (17)0.8627 (7)0.36124 (16)0.0433 (10)0.658 (12)
N2B0.0251 (2)0.9875 (5)0.3257 (2)0.0126 (6)0.658 (12)
C20B0.0845 (3)1.0357 (9)0.3540 (2)0.0160 (14)0.658 (12)
C21B0.1069 (2)1.0054 (8)0.4280 (3)0.0175 (13)0.658 (12)
C22B0.1588 (4)1.0456 (16)0.4820 (4)0.0235 (17)0.658 (12)
H22B0.18841.09450.47420.028*0.658 (12)
C23B0.1665 (3)1.0115 (9)0.5491 (4)0.0254 (13)0.658 (12)
H23B0.20181.03690.58620.031*0.658 (12)
C24B0.1228 (2)0.9414 (8)0.56112 (18)0.0370 (11)0.658 (12)
H24B0.12930.91800.60610.044*0.658 (12)
C25B0.0686 (2)0.9044 (8)0.50666 (16)0.0413 (14)0.658 (12)
H25B0.03880.85690.51460.050*0.658 (12)
C26B0.0612 (2)0.9412 (6)0.44076 (18)0.0250 (8)0.658 (12)
C27B0.00860 (19)0.9190 (6)0.37426 (18)0.0258 (8)0.658 (12)
O3X0.1052 (6)1.1164 (11)0.3266 (7)0.0297 (19)0.342 (12)
O4X0.0235 (4)0.7929 (13)0.3521 (4)0.046 (3)0.342 (12)
N2X0.0342 (4)0.9593 (9)0.3252 (5)0.0195 (16)0.342 (12)
C20X0.0880 (7)1.0363 (19)0.3594 (6)0.029 (4)0.342 (12)
C21X0.1074 (6)1.0017 (19)0.4334 (6)0.031 (4)0.342 (12)
C22X0.1601 (7)1.041 (2)0.4886 (8)0.022 (3)0.342 (12)
H22C0.18701.10650.48380.026*0.342 (12)
C23X0.1700 (6)0.9752 (17)0.5524 (8)0.029 (3)0.342 (12)
H23C0.20361.00110.59160.034*0.342 (12)
C24X0.1306 (3)0.8728 (15)0.5579 (4)0.0333 (18)0.342 (12)
H24C0.13780.83490.60120.040*0.342 (12)
C25X0.0804 (3)0.8241 (14)0.5006 (3)0.035 (2)0.342 (12)
H25C0.05520.75200.50440.042*0.342 (12)
C26X0.0705 (3)0.8894 (11)0.4379 (3)0.0227 (14)0.342 (12)
C27X0.0197 (3)0.8682 (12)0.3690 (4)0.0273 (16)0.342 (12)
H1NA0.5124 (11)0.351 (3)0.2695 (12)0.025 (5)*
H1OB0.0450 (15)0.749 (4)0.1599 (18)0.056 (9)*
H1NB0.0342 (13)1.066 (3)0.2407 (14)0.039 (7)*
H1OA0.4311 (13)0.675 (3)0.1226 (16)0.045 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0258 (5)0.0597 (8)0.0288 (5)0.0058 (5)0.0165 (4)0.0077 (5)
F2A0.0285 (6)0.0497 (8)0.0364 (6)0.0065 (5)0.0057 (5)0.0214 (6)
O1A0.0166 (5)0.0276 (6)0.0250 (5)0.0069 (4)0.0063 (4)0.0011 (4)
O2A0.0227 (5)0.0169 (5)0.0397 (7)0.0032 (4)0.0190 (5)0.0006 (5)
O3A0.0209 (5)0.0303 (6)0.0285 (6)0.0039 (5)0.0086 (4)0.0093 (5)
O4A0.0297 (6)0.0501 (9)0.0396 (7)0.0206 (6)0.0186 (6)0.0213 (7)
N1A0.0193 (5)0.0159 (5)0.0262 (6)0.0013 (4)0.0126 (5)0.0009 (5)
N2A0.0183 (5)0.0200 (6)0.0237 (6)0.0035 (4)0.0109 (5)0.0040 (5)
C1A0.0204 (6)0.0252 (7)0.0201 (6)0.0039 (5)0.0082 (5)0.0006 (5)
C2A0.0200 (6)0.0328 (8)0.0239 (7)0.0049 (6)0.0096 (6)0.0002 (6)
C3A0.0198 (6)0.0364 (9)0.0222 (7)0.0011 (6)0.0098 (5)0.0009 (6)
C4A0.0219 (7)0.0303 (8)0.0262 (7)0.0007 (6)0.0101 (6)0.0050 (6)
C5A0.0204 (6)0.0226 (7)0.0273 (7)0.0022 (5)0.0103 (6)0.0030 (6)
C6A0.0174 (6)0.0196 (6)0.0196 (6)0.0004 (5)0.0064 (5)0.0029 (5)
C7A0.0173 (6)0.0168 (6)0.0202 (6)0.0002 (5)0.0067 (5)0.0034 (5)
C8A0.0167 (6)0.0195 (6)0.0192 (6)0.0018 (5)0.0047 (5)0.0018 (5)
C9A0.0142 (5)0.0171 (6)0.0222 (6)0.0019 (5)0.0050 (5)0.0028 (5)
C10A0.0157 (5)0.0151 (6)0.0223 (6)0.0001 (4)0.0081 (5)0.0022 (5)
C11A0.0151 (5)0.0149 (6)0.0220 (6)0.0004 (4)0.0069 (5)0.0010 (5)
C12A0.0158 (5)0.0179 (6)0.0218 (6)0.0014 (5)0.0077 (5)0.0010 (5)
C13A0.0151 (5)0.0180 (6)0.0231 (6)0.0002 (5)0.0072 (5)0.0032 (5)
C14A0.0196 (6)0.0235 (7)0.0218 (7)0.0008 (5)0.0092 (5)0.0039 (5)
C15A0.0230 (7)0.0343 (9)0.0218 (7)0.0068 (6)0.0076 (6)0.0059 (6)
C16A0.0202 (7)0.0359 (9)0.0303 (8)0.0048 (6)0.0015 (6)0.0153 (7)
C17A0.0199 (7)0.0245 (8)0.0441 (10)0.0032 (6)0.0064 (7)0.0115 (7)
C18A0.0190 (6)0.0201 (7)0.0350 (8)0.0013 (5)0.0094 (6)0.0042 (6)
C19A0.0162 (6)0.0151 (6)0.0252 (7)0.0017 (5)0.0088 (5)0.0030 (5)
C20A0.0164 (6)0.0167 (6)0.0248 (7)0.0002 (5)0.0089 (5)0.0003 (5)
C21A0.0180 (6)0.0190 (6)0.0237 (7)0.0007 (5)0.0098 (5)0.0008 (5)
C22A0.0200 (7)0.0314 (8)0.0302 (8)0.0005 (6)0.0123 (6)0.0010 (6)
C23A0.0275 (8)0.0342 (9)0.0346 (9)0.0036 (7)0.0201 (7)0.0032 (7)
C24A0.0391 (9)0.0312 (9)0.0304 (8)0.0017 (7)0.0228 (8)0.0001 (7)
C25A0.0365 (9)0.0321 (9)0.0282 (8)0.0073 (7)0.0187 (7)0.0083 (7)
C26A0.0239 (7)0.0223 (7)0.0247 (7)0.0032 (5)0.0126 (6)0.0029 (6)
C27A0.0226 (7)0.0252 (7)0.0271 (7)0.0067 (6)0.0125 (6)0.0067 (6)
F1B0.0284 (5)0.0549 (8)0.0146 (4)0.0039 (5)0.0031 (4)0.0014 (4)
F2B0.0402 (7)0.0562 (8)0.0434 (7)0.0062 (6)0.0253 (6)0.0177 (6)
O1B0.0192 (5)0.0426 (7)0.0199 (5)0.0090 (5)0.0064 (4)0.0035 (5)
O2B0.0266 (6)0.0232 (6)0.0206 (5)0.0025 (4)0.0038 (4)0.0028 (4)
N1B0.0320 (7)0.0231 (6)0.0139 (5)0.0007 (5)0.0042 (5)0.0005 (5)
C1B0.0167 (6)0.0271 (7)0.0197 (6)0.0020 (5)0.0083 (5)0.0008 (5)
C2B0.0173 (6)0.0309 (8)0.0207 (7)0.0023 (6)0.0052 (5)0.0005 (6)
C3B0.0227 (7)0.0315 (8)0.0144 (6)0.0039 (6)0.0040 (5)0.0004 (6)
C4B0.0224 (7)0.0413 (10)0.0175 (6)0.0001 (6)0.0085 (5)0.0048 (6)
C5B0.0181 (6)0.0369 (9)0.0172 (6)0.0024 (6)0.0062 (5)0.0034 (6)
C6B0.0174 (6)0.0234 (7)0.0153 (6)0.0023 (5)0.0063 (5)0.0016 (5)
C7B0.0173 (6)0.0239 (7)0.0160 (6)0.0000 (5)0.0067 (5)0.0017 (5)
C8B0.0185 (6)0.0313 (8)0.0176 (6)0.0021 (6)0.0083 (5)0.0015 (6)
C9B0.0166 (6)0.0258 (7)0.0183 (6)0.0010 (5)0.0069 (5)0.0019 (5)
C10B0.0194 (6)0.0184 (6)0.0152 (6)0.0010 (5)0.0061 (5)0.0009 (5)
C11B0.0207 (6)0.0174 (6)0.0172 (6)0.0004 (5)0.0081 (5)0.0002 (5)
C12B0.0182 (6)0.0222 (7)0.0173 (6)0.0017 (5)0.0066 (5)0.0003 (5)
C13B0.0216 (6)0.0215 (7)0.0176 (6)0.0007 (5)0.0078 (5)0.0032 (5)
C14B0.0318 (8)0.0251 (7)0.0233 (7)0.0023 (6)0.0152 (6)0.0019 (6)
C15B0.0342 (9)0.0371 (9)0.0256 (8)0.0010 (7)0.0168 (7)0.0050 (7)
C16B0.0249 (7)0.0402 (10)0.0276 (8)0.0019 (7)0.0120 (6)0.0136 (7)
C17B0.0236 (7)0.0280 (8)0.0296 (8)0.0054 (6)0.0057 (6)0.0087 (6)
C18B0.0214 (6)0.0227 (7)0.0227 (7)0.0015 (5)0.0052 (5)0.0030 (6)
C19B0.0224 (6)0.0187 (6)0.0166 (6)0.0033 (5)0.0055 (5)0.0023 (5)
O3B0.0236 (14)0.0203 (19)0.0250 (11)0.0081 (13)0.0175 (10)0.0056 (12)
O4B0.0345 (14)0.061 (3)0.0298 (12)0.0243 (16)0.0094 (10)0.0012 (14)
N2B0.0137 (13)0.0123 (14)0.0111 (9)0.0031 (11)0.0045 (9)0.0000 (10)
C20B0.022 (2)0.019 (3)0.0083 (13)0.0040 (17)0.0074 (12)0.0013 (13)
C21B0.0114 (16)0.024 (3)0.017 (2)0.0079 (15)0.0058 (14)0.0025 (16)
C22B0.025 (3)0.027 (3)0.019 (2)0.004 (2)0.0098 (19)0.0037 (18)
C23B0.020 (2)0.030 (3)0.0182 (16)0.000 (2)0.0001 (13)0.0004 (17)
C24B0.0369 (19)0.052 (3)0.0166 (12)0.0129 (19)0.0060 (12)0.0039 (16)
C25B0.0365 (19)0.066 (3)0.0178 (12)0.027 (2)0.0075 (11)0.0057 (15)
C26B0.0249 (16)0.031 (2)0.0163 (11)0.0068 (14)0.0062 (10)0.0033 (13)
C27B0.0251 (15)0.033 (2)0.0170 (11)0.0101 (14)0.0070 (10)0.0006 (13)
O3X0.036 (3)0.016 (3)0.049 (4)0.014 (2)0.029 (2)0.010 (3)
O4X0.034 (3)0.057 (5)0.029 (3)0.028 (3)0.005 (2)0.015 (3)
N2X0.023 (3)0.018 (3)0.018 (2)0.012 (2)0.009 (2)0.001 (2)
C20X0.022 (5)0.012 (5)0.055 (8)0.005 (4)0.017 (5)0.006 (5)
C21X0.052 (7)0.034 (7)0.012 (4)0.009 (5)0.017 (4)0.001 (3)
C22X0.008 (4)0.022 (6)0.029 (5)0.002 (3)0.001 (3)0.011 (4)
C23X0.020 (3)0.041 (8)0.021 (3)0.013 (4)0.005 (2)0.002 (4)
C24X0.023 (2)0.053 (5)0.021 (3)0.000 (3)0.0058 (19)0.008 (3)
C25X0.022 (2)0.057 (6)0.024 (3)0.006 (3)0.0072 (19)0.013 (3)
C26X0.016 (2)0.029 (4)0.020 (2)0.003 (2)0.0045 (17)0.006 (2)
C27X0.022 (3)0.033 (4)0.022 (3)0.004 (3)0.005 (2)0.004 (3)
Geometric parameters (Å, º) top
F1A—C3A1.3585 (19)C1B—C2B1.392 (2)
F2A—C16A1.359 (2)C1B—C6B1.399 (2)
O1A—C9A1.3577 (18)C1B—H1BA0.9300
O1A—H1OA0.82 (3)C2B—C3B1.377 (2)
O2A—C19A1.2449 (18)C2B—H2BA0.9300
O3A—C20A1.200 (2)C3B—C4B1.378 (2)
O4A—C27A1.200 (2)C4B—C5B1.391 (2)
N1A—C19A1.346 (2)C4B—H4BA0.9300
N1A—N2A1.3723 (18)C5B—C6B1.396 (2)
N1A—H1NA0.80 (3)C5B—H5BA0.9300
N2A—C27A1.406 (2)C6B—C7B1.480 (2)
N2A—C20A1.4123 (19)C7B—C8B1.386 (2)
C1A—C2A1.387 (2)C7B—C12B1.401 (2)
C1A—C6A1.400 (2)C8B—C9B1.391 (2)
C1A—H1AA0.9300C8B—H8BA0.9300
C2A—C3A1.383 (3)C9B—C10B1.415 (2)
C2A—H2AA0.9300C10B—C11B1.421 (2)
C3A—C4A1.376 (2)C10B—C19B1.482 (2)
C4A—C5A1.389 (2)C11B—C12B1.393 (2)
C4A—H4AA0.9300C11B—C13B1.493 (2)
C5A—C6A1.400 (2)C12B—H12B0.9300
C5A—H5AA0.9300C13B—C18B1.398 (2)
C6A—C7A1.480 (2)C13B—C14B1.400 (2)
C7A—C8A1.391 (2)C14B—C15B1.393 (2)
C7A—C12A1.402 (2)C14B—H14B0.9300
C8A—C9A1.392 (2)C15B—C16B1.379 (3)
C8A—H8AA0.9300C15B—H15B0.9300
C9A—C10A1.413 (2)C16B—C17B1.377 (3)
C10A—C11A1.421 (2)C17B—C18B1.394 (2)
C10A—C19A1.484 (2)C17B—H17B0.9300
C11A—C12A1.392 (2)C18B—H18B0.9300
C11A—C13A1.485 (2)O3B—C20B1.214 (5)
C12A—H12A0.9300O4B—C27B1.197 (4)
C13A—C14A1.393 (2)N2B—C27B1.408 (5)
C13A—C18A1.402 (2)N2B—C20B1.410 (6)
C14A—C15A1.394 (2)C20B—C21B1.463 (6)
C14A—H14A0.9300C21B—C22B1.369 (7)
C15A—C16A1.373 (3)C21B—C26B1.401 (5)
C15A—H15A0.9300C22B—C23B1.400 (8)
C16A—C17A1.375 (3)C22B—H22B0.9300
C17A—C18A1.390 (3)C23B—C24B1.370 (7)
C17A—H17A0.9300C23B—H23B0.9300
C18A—H18A0.9300C24B—C25B1.401 (5)
C20A—C21A1.485 (2)C24B—H24B0.9300
C21A—C22A1.384 (2)C25B—C26B1.381 (4)
C21A—C26A1.390 (2)C25B—H25B0.9300
C22A—C23A1.400 (3)C26B—C27B1.484 (5)
C22A—H22A0.9300O3X—C20X1.202 (12)
C23A—C24A1.386 (3)O4X—C27X1.190 (8)
C23A—H23A0.9300N2X—C27X1.402 (11)
C24A—C25A1.398 (3)N2X—C20X1.407 (12)
C24A—H24A0.9300C20X—C21X1.480 (12)
C25A—C26A1.382 (2)C21X—C22X1.389 (12)
C25A—H25A0.9300C21X—C26X1.395 (12)
C26A—C27A1.487 (2)C22X—C23X1.410 (13)
F1B—C3B1.3587 (18)C22X—H22C0.9300
F2B—C16B1.357 (2)C23X—C24X1.384 (12)
O1B—C9B1.3558 (19)C23X—H23C0.9300
O1B—H1OB0.88 (3)C24X—C25X1.400 (9)
O2B—C19B1.245 (2)C24X—H24C0.9300
N1B—C19B1.349 (2)C25X—C26X1.385 (8)
N1B—N2B1.363 (5)C25X—H25C0.9300
N1B—N2X1.432 (11)C26X—C27X1.496 (8)
N1B—H1NB0.91 (3)
C9A—O1A—H1OA109 (2)C2B—C3B—C4B123.13 (14)
C19A—N1A—N2A116.80 (13)C3B—C4B—C5B118.07 (15)
C19A—N1A—H1NA125.1 (17)C3B—C4B—H4BA121.0
N2A—N1A—H1NA118.0 (17)C5B—C4B—H4BA121.0
N1A—N2A—C27A122.39 (13)C4B—C5B—C6B120.99 (14)
N1A—N2A—C20A123.09 (13)C4B—C5B—H5BA119.5
C27A—N2A—C20A112.85 (12)C6B—C5B—H5BA119.5
C2A—C1A—C6A121.59 (15)C5B—C6B—C1B118.86 (14)
C2A—C1A—H1AA119.2C5B—C6B—C7B120.18 (13)
C6A—C1A—H1AA119.2C1B—C6B—C7B120.92 (13)
C3A—C2A—C1A117.94 (15)C8B—C7B—C12B118.82 (14)
C3A—C2A—H2AA121.0C8B—C7B—C6B119.80 (13)
C1A—C2A—H2AA121.0C12B—C7B—C6B121.34 (13)
F1A—C3A—C4A118.46 (16)C7B—C8B—C9B120.65 (14)
F1A—C3A—C2A118.65 (15)C7B—C8B—H8BA119.7
C4A—C3A—C2A122.89 (15)C9B—C8B—H8BA119.7
C3A—C4A—C5A118.18 (16)O1B—C9B—C8B116.02 (14)
C3A—C4A—H4AA120.9O1B—C9B—C10B123.05 (13)
C5A—C4A—H4AA120.9C8B—C9B—C10B120.93 (14)
C4A—C5A—C6A121.40 (15)C9B—C10B—C11B118.48 (13)
C4A—C5A—H5AA119.3C9B—C10B—C19B115.99 (13)
C6A—C5A—H5AA119.3C11B—C10B—C19B125.53 (13)
C1A—C6A—C5A117.98 (14)C12B—C11B—C10B118.96 (13)
C1A—C6A—C7A121.14 (14)C12B—C11B—C13B116.33 (13)
C5A—C6A—C7A120.89 (14)C10B—C11B—C13B124.69 (13)
C8A—C7A—C12A117.94 (14)C11B—C12B—C7B122.08 (14)
C8A—C7A—C6A121.18 (14)C11B—C12B—H12B119.0
C12A—C7A—C6A120.83 (13)C7B—C12B—H12B119.0
C7A—C8A—C9A121.18 (14)C18B—C13B—C14B118.75 (15)
C7A—C8A—H8AA119.4C18B—C13B—C11B119.71 (14)
C9A—C8A—H8AA119.4C14B—C13B—C11B121.49 (14)
O1A—C9A—C8A115.45 (14)C15B—C14B—C13B120.54 (17)
O1A—C9A—C10A123.68 (14)C15B—C14B—H14B119.7
C8A—C9A—C10A120.86 (13)C13B—C14B—H14B119.7
C9A—C10A—C11A118.21 (13)C16B—C15B—C14B118.62 (18)
C9A—C10A—C19A116.23 (13)C16B—C15B—H15B120.7
C11A—C10A—C19A125.55 (14)C14B—C15B—H15B120.7
C12A—C11A—C10A119.21 (14)F2B—C16B—C17B118.84 (18)
C12A—C11A—C13A115.87 (13)F2B—C16B—C15B118.30 (18)
C10A—C11A—C13A124.52 (13)C17B—C16B—C15B122.85 (16)
C11A—C12A—C7A122.42 (13)C16B—C17B—C18B117.99 (17)
C11A—C12A—H12A118.8C16B—C17B—H17B121.0
C7A—C12A—H12A118.8C18B—C17B—H17B121.0
C14A—C13A—C18A118.89 (15)C17B—C18B—C13B121.24 (17)
C14A—C13A—C11A120.77 (14)C17B—C18B—H18B119.4
C18A—C13A—C11A119.99 (14)C13B—C18B—H18B119.4
C13A—C14A—C15A120.73 (16)O2B—C19B—N1B119.59 (14)
C13A—C14A—H14A119.6O2B—C19B—C10B121.91 (14)
C15A—C14A—H14A119.6N1B—C19B—C10B118.46 (14)
C16A—C15A—C14A118.26 (18)N1B—N2B—C27B124.5 (3)
C16A—C15A—H15A120.9N1B—N2B—C20B121.4 (4)
C14A—C15A—H15A120.9C27B—N2B—C20B113.4 (4)
F2A—C16A—C15A118.06 (19)O3B—C20B—N2B127.0 (5)
F2A—C16A—C17A118.72 (18)O3B—C20B—C21B128.0 (6)
C15A—C16A—C17A123.20 (16)N2B—C20B—C21B105.0 (4)
C16A—C17A—C18A118.10 (17)C22B—C21B—C26B119.9 (6)
C16A—C17A—H17A121.0C22B—C21B—C20B131.0 (5)
C18A—C17A—H17A121.0C26B—C21B—C20B108.5 (4)
C17A—C18A—C13A120.81 (17)C21B—C22B—C23B118.7 (7)
C17A—C18A—H18A119.6C21B—C22B—H22B120.7
C13A—C18A—H18A119.6C23B—C22B—H22B120.7
O2A—C19A—N1A119.49 (14)C24B—C23B—C22B121.1 (6)
O2A—C19A—C10A121.43 (14)C24B—C23B—H23B119.5
N1A—C19A—C10A119.00 (13)C22B—C23B—H23B119.5
O3A—C20A—N2A124.66 (14)C23B—C24B—C25B121.0 (4)
O3A—C20A—C21A130.74 (14)C23B—C24B—H24B119.5
N2A—C20A—C21A104.60 (13)C25B—C24B—H24B119.5
C22A—C21A—C26A121.34 (15)C26B—C25B—C24B117.3 (3)
C22A—C21A—C20A129.87 (15)C26B—C25B—H25B121.3
C26A—C21A—C20A108.77 (13)C24B—C25B—H25B121.3
C21A—C22A—C23A117.16 (16)C25B—C26B—C21B121.8 (4)
C21A—C22A—H22A121.4C25B—C26B—C27B129.0 (3)
C23A—C22A—H22A121.4C21B—C26B—C27B109.2 (3)
C24A—C23A—C22A121.41 (16)O4B—C27B—N2B125.0 (4)
C24A—C23A—H23A119.3O4B—C27B—C26B131.4 (3)
C22A—C23A—H23A119.3N2B—C27B—C26B103.6 (3)
C23A—C24A—C25A121.07 (17)C27X—N2X—C20X113.4 (9)
C23A—C24A—H24A119.5C27X—N2X—N1B120.0 (8)
C25A—C24A—H24A119.5C20X—N2X—N1B125.5 (9)
C26A—C25A—C24A117.23 (17)O3X—C20X—N2X119.1 (12)
C26A—C25A—H25A121.4O3X—C20X—C21X135.5 (12)
C24A—C25A—H25A121.4N2X—C20X—C21X105.2 (9)
C25A—C26A—C21A121.78 (15)C22X—C21X—C26X122.5 (10)
C25A—C26A—C27A129.37 (16)C22X—C21X—C20X128.3 (11)
C21A—C26A—C27A108.85 (14)C26X—C21X—C20X107.4 (9)
O4A—C27A—N2A125.13 (15)C21X—C22X—C23X115.6 (12)
O4A—C27A—C26A130.23 (16)C21X—C22X—H22C122.2
N2A—C27A—C26A104.65 (13)C23X—C22X—H22C122.2
C9B—O1B—H1OB109 (2)C24X—C23X—C22X121.3 (12)
C19B—N1B—N2B123.2 (2)C24X—C23X—H23C119.4
C19B—N1B—N2X109.5 (3)C22X—C23X—H23C119.4
N2B—N1B—N2X13.9 (3)C23X—C24X—C25X122.4 (9)
C19B—N1B—H1NB122.3 (17)C23X—C24X—H24C118.8
N2B—N1B—H1NB114.5 (18)C25X—C24X—H24C118.8
N2X—N1B—H1NB128.1 (18)C26X—C25X—C24X116.3 (6)
C2B—C1B—C6B120.78 (14)C26X—C25X—H25C121.8
C2B—C1B—H1BA119.6C24X—C25X—H25C121.8
C6B—C1B—H1BA119.6C25X—C26X—C21X121.2 (7)
C3B—C2B—C1B118.16 (14)C25X—C26X—C27X129.2 (6)
C3B—C2B—H2BA120.9C21X—C26X—C27X109.4 (7)
C1B—C2B—H2BA120.9O4X—C27X—N2X125.7 (7)
F1B—C3B—C2B118.45 (15)O4X—C27X—C26X130.7 (6)
F1B—C3B—C4B118.42 (15)N2X—C27X—C26X103.6 (6)
C19A—N1A—N2A—C27A76.28 (19)O1B—C9B—C10B—C11B176.72 (15)
C19A—N1A—N2A—C20A87.92 (18)C8B—C9B—C10B—C11B3.3 (2)
C6A—C1A—C2A—C3A0.8 (3)O1B—C9B—C10B—C19B3.9 (2)
C1A—C2A—C3A—F1A179.92 (16)C8B—C9B—C10B—C19B176.07 (15)
C1A—C2A—C3A—C4A0.1 (3)C9B—C10B—C11B—C12B2.0 (2)
F1A—C3A—C4A—C5A178.67 (16)C19B—C10B—C11B—C12B177.40 (14)
C2A—C3A—C4A—C5A1.3 (3)C9B—C10B—C11B—C13B176.17 (15)
C3A—C4A—C5A—C6A1.7 (3)C19B—C10B—C11B—C13B4.5 (2)
C2A—C1A—C6A—C5A0.4 (2)C10B—C11B—C12B—C7B0.2 (2)
C2A—C1A—C6A—C7A179.18 (15)C13B—C11B—C12B—C7B178.43 (15)
C4A—C5A—C6A—C1A0.9 (2)C8B—C7B—C12B—C11B0.9 (2)
C4A—C5A—C6A—C7A179.52 (15)C6B—C7B—C12B—C11B178.66 (15)
C1A—C6A—C7A—C8A162.32 (15)C12B—C11B—C13B—C18B52.7 (2)
C5A—C6A—C7A—C8A18.1 (2)C10B—C11B—C13B—C18B129.13 (17)
C1A—C6A—C7A—C12A20.4 (2)C12B—C11B—C13B—C14B124.57 (17)
C5A—C6A—C7A—C12A159.18 (15)C10B—C11B—C13B—C14B53.6 (2)
C12A—C7A—C8A—C9A1.3 (2)C18B—C13B—C14B—C15B0.9 (3)
C6A—C7A—C8A—C9A176.05 (14)C11B—C13B—C14B—C15B178.20 (16)
C7A—C8A—C9A—O1A176.28 (14)C13B—C14B—C15B—C16B0.3 (3)
C7A—C8A—C9A—C10A4.6 (2)C14B—C15B—C16B—F2B179.41 (17)
O1A—C9A—C10A—C11A175.94 (14)C14B—C15B—C16B—C17B0.3 (3)
C8A—C9A—C10A—C11A5.0 (2)F2B—C16B—C17B—C18B179.42 (16)
O1A—C9A—C10A—C19A2.9 (2)C15B—C16B—C17B—C18B0.3 (3)
C8A—C9A—C10A—C19A176.11 (13)C16B—C17B—C18B—C13B0.3 (2)
C9A—C10A—C11A—C12A2.3 (2)C14B—C13B—C18B—C17B0.9 (2)
C19A—C10A—C11A—C12A178.97 (14)C11B—C13B—C18B—C17B178.25 (15)
C9A—C10A—C11A—C13A170.18 (14)N2B—N1B—C19B—O2B4.3 (3)
C19A—C10A—C11A—C13A8.6 (2)N2X—N1B—C19B—O2B2.1 (5)
C10A—C11A—C12A—C7A1.0 (2)N2B—N1B—C19B—C10B177.9 (2)
C13A—C11A—C12A—C7A174.04 (14)N2X—N1B—C19B—C10B179.9 (4)
C8A—C7A—C12A—C11A1.5 (2)C9B—C10B—C19B—O2B25.2 (2)
C6A—C7A—C12A—C11A178.84 (14)C11B—C10B—C19B—O2B155.45 (16)
C12A—C11A—C13A—C14A128.03 (15)C9B—C10B—C19B—N1B152.55 (15)
C10A—C11A—C13A—C14A44.6 (2)C11B—C10B—C19B—N1B26.8 (2)
C12A—C11A—C13A—C18A45.1 (2)C19B—N1B—N2B—C27B91.8 (4)
C10A—C11A—C13A—C18A142.28 (15)N2X—N1B—N2B—C27B100 (2)
C18A—C13A—C14A—C15A0.8 (2)C19B—N1B—N2B—C20B77.4 (6)
C11A—C13A—C14A—C15A172.33 (14)N2X—N1B—N2B—C20B69 (2)
C13A—C14A—C15A—C16A0.2 (2)N1B—N2B—C20B—O3B3.6 (11)
C14A—C15A—C16A—F2A177.24 (15)C27B—N2B—C20B—O3B173.9 (7)
C14A—C15A—C16A—C17A1.1 (3)N1B—N2B—C20B—C21B174.7 (5)
F2A—C16A—C17A—C18A177.35 (16)C27B—N2B—C20B—C21B4.4 (8)
C15A—C16A—C17A—C18A1.0 (3)O3B—C20B—C21B—C22B11.1 (18)
C16A—C17A—C18A—C13A0.1 (3)N2B—C20B—C21B—C22B170.6 (12)
C14A—C13A—C18A—C17A1.0 (2)O3B—C20B—C21B—C26B178.0 (8)
C11A—C13A—C18A—C17A172.26 (15)N2B—C20B—C21B—C26B0.2 (8)
N2A—N1A—C19A—O2A6.3 (2)C26B—C21B—C22B—C23B4.5 (18)
N2A—N1A—C19A—C10A176.82 (13)C20B—C21B—C22B—C23B174.5 (10)
C9A—C10A—C19A—O2A32.5 (2)C21B—C22B—C23B—C24B1.0 (18)
C11A—C10A—C19A—O2A146.25 (16)C22B—C23B—C24B—C25B1.4 (12)
C9A—C10A—C19A—N1A144.29 (14)C23B—C24B—C25B—C26B0.1 (8)
C11A—C10A—C19A—N1A36.9 (2)C24B—C25B—C26B—C21B3.5 (8)
N1A—N2A—C20A—O3A8.2 (2)C24B—C25B—C26B—C27B178.5 (5)
C27A—N2A—C20A—O3A173.73 (16)C22B—C21B—C26B—C25B5.9 (12)
N1A—N2A—C20A—C21A171.17 (13)C20B—C21B—C26B—C25B178.0 (6)
C27A—N2A—C20A—C21A5.62 (17)C22B—C21B—C26B—C27B175.7 (9)
O3A—C20A—C21A—C22A3.3 (3)C20B—C21B—C26B—C27B3.7 (8)
N2A—C20A—C21A—C22A177.46 (17)N1B—N2B—C27B—O4B5.8 (7)
O3A—C20A—C21A—C26A175.39 (18)C20B—N2B—C27B—O4B175.8 (6)
N2A—C20A—C21A—C26A3.90 (17)N1B—N2B—C27B—C26B176.4 (4)
C26A—C21A—C22A—C23A0.6 (3)C20B—N2B—C27B—C26B6.4 (6)
C20A—C21A—C22A—C23A177.93 (17)C25B—C26B—C27B—O4B1.7 (8)
C21A—C22A—C23A—C24A0.0 (3)C21B—C26B—C27B—O4B176.4 (6)
C22A—C23A—C24A—C25A0.9 (3)C25B—C26B—C27B—N2B175.8 (5)
C23A—C24A—C25A—C26A1.1 (3)C21B—C26B—C27B—N2B6.0 (6)
C24A—C25A—C26A—C21A0.6 (3)C19B—N1B—N2X—C27X90.1 (6)
C24A—C25A—C26A—C27A178.80 (19)N2B—N1B—N2X—C27X82 (2)
C22A—C21A—C26A—C25A0.3 (3)C19B—N1B—N2X—C20X102.4 (11)
C20A—C21A—C26A—C25A178.50 (16)N2B—N1B—N2X—C20X85 (2)
C22A—C21A—C26A—C27A179.78 (16)C27X—N2X—C20X—O3X179.1 (13)
C20A—C21A—C26A—C27A0.99 (19)N1B—N2X—C20X—O3X13 (2)
N1A—N2A—C27A—O4A9.3 (3)C27X—N2X—C20X—C21X5.4 (16)
C20A—N2A—C27A—O4A174.96 (18)N1B—N2X—C20X—C21X162.9 (10)
N1A—N2A—C27A—C26A170.70 (14)O3X—C20X—C21X—C22X11 (4)
C20A—N2A—C27A—C26A5.04 (18)N2X—C20X—C21X—C22X175 (2)
C25A—C26A—C27A—O4A1.8 (3)O3X—C20X—C21X—C26X176 (2)
C21A—C26A—C27A—O4A177.7 (2)N2X—C20X—C21X—C26X9.6 (18)
C25A—C26A—C27A—N2A178.24 (18)C26X—C21X—C22X—C23X9 (3)
C21A—C26A—C27A—N2A2.32 (19)C20X—C21X—C22X—C23X171.6 (19)
C6B—C1B—C2B—C3B0.5 (3)C21X—C22X—C23X—C24X3 (3)
C1B—C2B—C3B—F1B179.48 (16)C22X—C23X—C24X—C25X3 (2)
C1B—C2B—C3B—C4B0.9 (3)C23X—C24X—C25X—C26X2.9 (14)
F1B—C3B—C4B—C5B179.94 (17)C24X—C25X—C26X—C21X2.5 (15)
C2B—C3B—C4B—C5B0.4 (3)C24X—C25X—C26X—C27X176.2 (8)
C3B—C4B—C5B—C6B0.7 (3)C22X—C21X—C26X—C25X9 (2)
C4B—C5B—C6B—C1B1.1 (3)C20X—C21X—C26X—C25X174.8 (11)
C4B—C5B—C6B—C7B179.01 (17)C22X—C21X—C26X—C27X176.6 (17)
C2B—C1B—C6B—C5B0.5 (3)C20X—C21X—C26X—C27X10.4 (16)
C2B—C1B—C6B—C7B178.39 (15)C20X—N2X—C27X—O4X179.8 (11)
C5B—C6B—C7B—C8B40.4 (2)N1B—N2X—C27X—O4X10.9 (12)
C1B—C6B—C7B—C8B137.46 (17)C20X—N2X—C27X—C26X0.8 (11)
C5B—C6B—C7B—C12B141.92 (17)N1B—N2X—C27X—C26X169.7 (5)
C1B—C6B—C7B—C12B40.2 (2)C25X—C26X—C27X—O4X0.7 (15)
C12B—C7B—C8B—C9B0.4 (2)C21X—C26X—C27X—O4X173.5 (12)
C6B—C7B—C8B—C9B177.31 (15)C25X—C26X—C27X—N2X178.7 (8)
C7B—C8B—C9B—O1B177.45 (16)C21X—C26X—C27X—N2X7.1 (11)
C7B—C8B—C9B—C10B2.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O2Ai0.80 (3)2.02 (3)2.8000 (19)166 (3)
O1B—H1OB···O2B0.88 (3)1.79 (4)2.5663 (17)145 (4)
N1B—H1NB···O2Bii0.91 (3)2.04 (3)2.779 (2)138 (2)
O1A—H1OA···O2A0.82 (3)1.94 (3)2.6402 (18)143 (3)
C2A—H2AA···F2Aiii0.932.453.160 (2)133
C4B—H4BA···O3Biv0.932.413.271 (7)154
C14B—H14B···O3Bv0.932.443.293 (6)152
C25B—H25B···O1Bvi0.932.473.209 (3)136
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x, y+2, z; (v) x, y1/2, z+1/2; (vi) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC27H16F2N2O4
Mr470.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)24.8732 (10), 8.9875 (4), 21.3722 (9)
β (°) 114.921 (1)
V3)4332.9 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.41 × 0.31 × 0.14
Data collection
DiffractometerBruker APEX DUO CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.956, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
16713, 16713, 12698
Rint0.000
(sin θ/λ)max1)0.773
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.168, 1.05
No. of reflections16713
No. of parameters748
No. of restraints45
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.63, 0.90

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O2Ai0.80 (3)2.02 (3)2.8000 (19)166 (3)
O1B—H1OB···O2B0.88 (3)1.79 (4)2.5663 (17)145 (4)
N1B—H1NB···O2Bii0.91 (3)2.04 (3)2.779 (2)138 (2)
O1A—H1OA···O2A0.82 (3)1.94 (3)2.6402 (18)143 (3)
C2A—H2AA···F2Aiii0.932.453.160 (2)133
C4B—H4BA···O3Biv0.932.413.271 (7)154
C14B—H14B···O3Bv0.932.443.293 (6)152
C25B—H25B···O1Bvi0.932.473.209 (3)136
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x, y+2, z; (v) x, y1/2, z+1/2; (vi) x, y+3/2, z+1/2.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

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First citationFun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o163.  Web of Science CSD CrossRef IUCr Journals
First citationSamshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, 2011, M745.  CrossRef
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First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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Volume 68| Part 9| September 2012| Pages o2619-o2620
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