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The asymmetric unit of the title compound, C26H30FN3O, contains two crystallographically independent mol­ecules, the core skeletons of which have the same absolute configuration and almost identical conformations, except for differences in the orientation of the p-fluoro­phenyl ring. The tetra­hydro­pyridine ring adopts a half-chair conformation, while the cyclo­hexenone ring has a slightly distorted envelope conformation. The cyclo­hexane rings have chair conformations, sometimes slightly distorted. Intermolecular N-H...O, N-H...N and C-H...F interactions and an intramolecular C-H...N interaction are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103029159/sk1692sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103029159/sk1692Isup2.hkl
Contains datablock I

CCDC reference: 233142

Comment top

There has been considerable interest in the synthesis and biological activity of several heterocyclic steroids as extremely potent antiinflammatory agents (Gupta et al., 1996, and references therein). In the 17a-aza series, the presence of an α,β-unsaturated ketone produced compounds with good activity, while hydroxy and acetoxy derivatives were found to be inactive. The fusion of pyrazole ring systems at the 2,3- and 16,17-positions of azasteroids afforded compounds with enhanced antiinflammatory activity compared with standard drugs in the androstane series (Gupta et al., 1996). Crystal structure analyses have been carried out in order to study the influence of the fused pyrazole moiety on the steroid skeleton. The present study extends our ongoing investigation of a series of similar ring-A– or ring-D-modified steroids. In a previous paper, we reported two ring-A-modified steroids, namely 2'-(p-fluorophenyl)-4-azapyrazolo[4',3':2,3]-5α-androstan-17β-yl acetate and 2'-(p-fluorophenyl)-4-azapyrazolo[4',3':2,3]-5α-androstan-17β-ol (Thamotharan et al., 2003). In this paper, we report the crystal and molecular structure of a ring-D-modified steroid, namely 2'-(p-fluorophenyl)-17a-aza-D-homo-4-androsteno[17,16 − c]pyrazol-3-one, (I). \sch

The crystals of (I) are enantiomerically pure. However, due to the absence of any significant anomalous scatterers in the compound, the absolute configuration of the molecule has not been determined by the X-ray diffraction experiment. The enantiomer used in the refinement was assumed to correspond with the configuration of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of (I).

There are two symmetry-independent molecules, A and B, in the asymmetric unit of (I), and these are depicted in Fig. 1. The corresponding bond lengths and angles for the independent molecules agree well with each other. Excluding the atoms of the p-fluorophenyl group, the core skeletons of the two molecules have the same absolute configuration and almost identical conformations, with only very minor differences in the puckering of some rings. The unweighted r.m.s. fit of the remaining non-H atoms of molecule A with the corresponding atoms of molecule B is 0.12 Å. The main difference between the conformations of the two molecules is the orientation of the plane of the p-fluorophenyl ring in molecule B, which is tilted by approximately 63° with respect to its orientation in molecule A. The angle between the mean planes through the p-fluorophenyl ring (excluding the F atom) and the pyrazole ring is 38.85 (11)° for molecule A and −23.86 (11)° for molecule B. Another difference between the two symmetry-independent molecules is that the positions of the lone electron pair and the H atom on atom N17B in molecule B are reversed with respect to their positions on atom N17A in molecule A. This effective inversion of the configuration at this N atom also has consequences for the hydrogen-bonding interactions, as described below.

In both independent molecules, the methyl groups C18 and C19 lie in the expected β orientation, while the geometry at the B/C and C/D ring junctions is all-trans. The C4C5 distances of 1.343 (3) and 1.346 (3) Å in molecules A and B, respectively, confirm the localization of the double bond at these positions.

The cyclohexenone ring A adopts a slightly distorted envelope conformation in both independent molecules, with the distortion being more severe and slightly towards a half-chair conformation in molecule A. Atoms C1A and C1B form the envelope flap in the respective molecules and the conformation of this ring is a consequence of the C4C5 alkene bond. The puckering parameters (Cremer & Pople, 1975) for this ring in molecule A are Q = 0.436 (2) Å, q2 = 0.347 (2) Å, q3 = 0.265 (2) Å, θ = 52.7 (3)° and ϕ2 = 12.2 (4)° for the atom sequence C1A—C5A/C10A, while for molecule B, Q = 0.450 (2) Å, q2 = 0.371 (2) Å, q3 = 0.254 (2) Å, θ = 55.7 (3)° and ϕ2 = 8.2 (3)° for the atom sequence C1B—C5B/C10B.

The steroidal ring B exists in a slightly distorted chair conformation in both molecules, with puckering parameters for molecule A [molecule B in brackets] of Q = 0.543 (2) Å [0.529 (2) Å], q2 = 0.099 (2) Å [0.082 (2) Å], q3 = 0.534 (2) Å [0.522 (2) Å], θ = 10.6 (2)° [9.2 (2)°] and ϕ2 = 195.1 (12)° [192.7 (14)°] for the atom sequence C5A—C10A [C5B—C10B].

Ring C has a chair conformation in both molecules, although it is slightly more distorted in molecule A than in molecule B. The puckering parameters for molecule A [molecule B in brackets] are Q = 0.559 (2) Å [0.570 (2) Å], q2 = 0.077 (2) Å [0.041 (2) Å], q3 = 0.554 (2) Å [0.568 (2) Å], θ = 7.6 (2)° [3.9 (2)°] and ϕ2 = 218.0 (15)° [207 (3)°] for the atom sequence C8A/C9A/C11A—C14A [C8B/C9B/C11B—C14B]. The tetrahydropyridine ring D of the steroid nucleus adopts a half-chair conformation in both molecules A and B, twisted on C13A—C14A and C13B—C14B, respectively. The ring is considerably strained as a consequence of the presence of the fused planar pyrazole ring. The puckering parameters for ring D in molecule A [molecule B in brackets] are Q = 0.497 (2) Å [0.480 (2) Å], q2 = 0.379 (2) Å [0.377 (2) Å], q3 = 0.323 (2) Å [0.297 (2) Å], θ = 49.6 (2)° [51.8 (2)°] and ϕ2 = 83.5 (3)° [94.4 (3)°] for the atom sequence N17A/C13A—C17A [N17B/C13B—C17B].

The pseudo-torsion angles C19A—C10A···C13A—C18A [−1.31 (15)°] in molecule A and C19B—C10B···C13B—C18B [1.88 (17)°] in molecule B provide a quantitative measure of the twist about the length of the molecule and show that the molecules in (I) are not twisted to any significant degree and, with the exception of the tilted p-fluorphenyl group, that the entire molecule is quite flat. The values are comparable with those of related structures (Thamotharan et al., 2003).

In (I), atom C24B forms a weak intramolecular C—H···N interaction (Table 1) with atom N17B of molecule B, which leads to a loop with a graph-set motif of S(6) (Bernstein et al., 1995). Atoms C27A and C27B are involved in weak intermolecular C—H···F interactions with atoms F26A and F26B, respectively, of two different adjacent molecules, and each interaction links the A and B molecules independently into chains which have graph-set motifs of C(4) and run parallel to the y axis. Atoms N17A and N17B participate in intermolecular N—H···O or N—H···N hydrogen bonds with atoms O3B and N21A, respectively, of two different neighbouring molecules. These interactions serve to cross-link molecules A with B and act cooperatively to produce chains of alternating A and B molecules which have a graph-set motif of C22(16) and run parallel to the y axis. Atom C4A acts as donor for a weak intermolecular C—H···N interaction with atom N21B of an adjacent molecule.

Experimental top

A solution of 2'-p-fluorophenyl-17a-aza-D-homo-5-androsteno[17,16 − c]pyrazol-3β-ol (0.5 g, 1.186 mmol) in cyclohexanone (5 ml) and toluene (100 ml) was slowly distilled while aluminium isopropoxide (1 g) in toluene (10 ml) was added to remove moisture. Distillation was continued for 30 min. The reaction mixture was refluxed for 4 h and allowed to stand overnight. The solution was filtered, the filtrate was steam distilled and the residue obtained was crystallized from ethyl acetate to afford (I) (institution code DPJ-255) (yield 0.35 g, 70.42%; m.p. 499–501 K).

Refinement top

The positions of the amine H atoms were determined from a difference Fourier map and refined freely along with their isotropic displacement parameters. The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å), with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00 Å) and were constrained to ride on their parent atoms. Due to the absence of any significant anomalous scatterers in (I), attempts to confirm the absolute structure by refinement of the Flack (1983) parameter in the presence of 5710 sets of Friedel equivalents led to an inconclusive value (Flack & Bernardinelli, 2000) of 0.2 (6). Therefore, the Friedel pairs were merged before the final refinement and the absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of (I). Reflections 003, 103, 012, 101, 110, 011, 002, 111, 102 and 101 were partially obscured by the beam stop and were omitted.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented by spheres of arbitrary radii.
2'-(p-fluorophenyl)-17a-aza-2'H-pyrazolo[4',3':16,17]-D-homoandrost-4-en-3-one top
Crystal data top
C26H30FN3OF(000) = 896
Mr = 419.53Dx = 1.301 Mg m3
Monoclinic, P21Melting point: 499 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 13.5243 (2) ÅCell parameters from 6708 reflections
b = 7.3983 (1) Åθ = 1.0–30.0°
c = 21.8934 (3) ŵ = 0.09 mm1
β = 102.1562 (8)°T = 160 K
V = 2141.47 (5) Å3Prism, colourless
Z = 40.30 × 0.28 × 0.15 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
5595 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.055
Horizontally mounted graphite crystal monochromatorθmax = 30.0°, θmin = 1.5°
Detector resolution: 9 pixels mm-1h = 019
ϕ and ω scans with κ offsetsk = 010
64206 measured reflectionsl = 3030
6714 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.2257P]
where P = (Fo2 + 2Fc2)/3
6704 reflections(Δ/σ)max < 0.001
571 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C26H30FN3OV = 2141.47 (5) Å3
Mr = 419.53Z = 4
Monoclinic, P21Mo Kα radiation
a = 13.5243 (2) ŵ = 0.09 mm1
b = 7.3983 (1) ÅT = 160 K
c = 21.8934 (3) Å0.30 × 0.28 × 0.15 mm
β = 102.1562 (8)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
5595 reflections with I > 2σ(I)
64206 measured reflectionsRint = 0.055
6714 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.23 e Å3
6704 reflectionsΔρmin = 0.19 e Å3
571 parameters
Special details top

Experimental. Solvent used: ethyl acetate Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.577 (1) Frames collected: 654 Seconds exposure per frame: 56 Degrees rotation per frame: 1.4 Crystal-Detector distance (mm): 33.00

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*/Ueq
F26A0.93563 (11)0.6916 (2)0.45681 (6)0.0608 (4)
O3A0.64070 (11)0.8096 (2)0.28067 (6)0.0440 (4)
N17A0.83048 (12)0.9618 (2)0.17080 (7)0.0274 (3)
H1710.8706 (16)0.889 (3)0.1948 (9)0.030 (6)*
N20A0.83126 (12)1.1636 (2)0.25918 (7)0.0319 (4)
N21A0.82075 (13)1.3467 (2)0.26969 (8)0.0359 (4)
C1A0.77864 (14)0.7205 (3)0.12396 (8)0.0287 (4)
H110.83370.63850.10380.034*
H120.71540.67810.11270.034*
C2A0.76691 (15)0.7073 (3)0.19464 (8)0.0349 (4)
H210.83300.73120.20570.042*
H220.74580.58310.20840.042*
C3A0.69016 (14)0.8396 (3)0.22810 (8)0.0335 (4)
C4A0.68109 (14)1.0100 (3)0.19577 (8)0.0328 (4)
H410.63671.09960.21730.039*
C5A0.73176 (14)1.0472 (3)0.13751 (8)0.0287 (4)
C6A0.72597 (16)1.2325 (3)0.11010 (9)0.0345 (4)
H610.66801.29820.13570.041*
H620.78831.30010.11240.041*
C7A0.71387 (15)1.2292 (3)0.04201 (8)0.0328 (4)
H710.72051.35370.02510.039*
H720.64541.18490.04050.039*
C8A0.79300 (13)1.1077 (3)0.00106 (8)0.0260 (4)
H810.86141.15630.00260.031*
C9A0.78460 (13)0.9162 (2)0.02945 (8)0.0250 (4)
H910.71300.87720.03220.030*
C10A0.80224 (13)0.9129 (3)0.09776 (8)0.0266 (4)
C11A0.85062 (14)0.7776 (3)0.01259 (8)0.0294 (4)
H1110.83440.65480.00460.035*
H1120.92270.80190.01290.035*
C12A0.83405 (15)0.7846 (3)0.07924 (8)0.0281 (4)
H1210.76340.74980.07940.034*
H1220.87940.69630.10530.034*
C13A0.85460 (13)0.9724 (3)0.10753 (7)0.0250 (4)
C14A0.78224 (13)1.1097 (2)0.06784 (8)0.0256 (4)
H1410.71171.07070.06840.031*
C15A0.79608 (14)1.3017 (3)0.09601 (8)0.0293 (4)
H1510.85691.35850.08590.035*
H1520.73671.37710.07780.035*
C16A0.80736 (14)1.2917 (3)0.16569 (9)0.0292 (4)
C17A0.82387 (14)1.1301 (3)0.19689 (8)0.0283 (4)
C18A0.96644 (13)1.0250 (3)0.11412 (9)0.0311 (4)
H1810.98071.13430.13980.047*
H1820.98031.04830.07270.047*
H1831.00960.92600.13410.047*
C19A0.91197 (14)0.9679 (3)0.10031 (9)0.0329 (4)
H1910.92080.96100.14350.049*
H1920.95970.88570.07410.049*
H1930.92471.09190.08490.049*
C22A0.80583 (15)1.4194 (3)0.21296 (9)0.0340 (4)
H2210.79521.54500.20520.041*
C23A0.85678 (14)1.0425 (3)0.31009 (8)0.0301 (4)
C24A0.81643 (15)0.8700 (3)0.30567 (9)0.0346 (4)
H2410.76970.83420.26900.042*
C25A0.84420 (16)0.7492 (3)0.35484 (9)0.0389 (5)
H2510.81910.62880.35180.047*
C26A0.90889 (16)0.8090 (4)0.40784 (9)0.0410 (5)
C27A0.94871 (15)0.9799 (4)0.41414 (9)0.0416 (5)
H2710.99291.01620.45190.050*
C28A0.92325 (14)1.0991 (3)0.36434 (9)0.0367 (5)
H2810.95081.21770.36720.044*
F26B0.50302 (12)0.1489 (3)0.04360 (6)0.0726 (5)
O3B1.00431 (10)0.2061 (2)0.77531 (6)0.0409 (3)
N17B0.63298 (12)0.3303 (2)0.34312 (7)0.0275 (3)
H1720.6866 (18)0.297 (4)0.3336 (10)0.042 (7)*
N20B0.57358 (12)0.5524 (2)0.26091 (7)0.0292 (3)
N21B0.54452 (12)0.7309 (2)0.25586 (7)0.0339 (4)
C1B0.85595 (15)0.0665 (3)0.62605 (8)0.0350 (4)
H130.82400.04710.60780.042*
H140.91310.09330.60570.042*
C2B0.89697 (17)0.0381 (3)0.69581 (9)0.0370 (5)
H230.84200.00700.71540.044*
H240.95100.05450.70190.044*
C3B0.93861 (14)0.2102 (3)0.72720 (8)0.0306 (4)
C4B0.89392 (15)0.3784 (3)0.70008 (8)0.0318 (4)
H420.91930.48860.71950.038*
C5B0.81865 (14)0.3871 (3)0.64901 (8)0.0277 (4)
C6B0.76515 (16)0.5618 (3)0.62932 (8)0.0355 (4)
H630.80610.66240.65120.043*
H640.69960.56150.64260.043*
C7B0.74563 (15)0.5966 (3)0.55868 (8)0.0303 (4)
H730.70170.70420.54860.036*
H740.81070.62290.54660.036*
C8B0.69525 (13)0.4355 (2)0.52090 (7)0.0247 (4)
H820.62760.41600.53140.030*
C9B0.76004 (13)0.2645 (2)0.54019 (8)0.0245 (3)
H920.82810.29050.53120.029*
C10B0.77796 (13)0.2208 (3)0.61146 (8)0.0269 (4)
C11B0.71825 (15)0.1016 (3)0.49992 (8)0.0305 (4)
H1130.76490.00210.51090.037*
H1140.65190.06700.50870.037*
C12B0.70572 (15)0.1435 (3)0.43066 (8)0.0308 (4)
H1230.77280.17040.42150.037*
H1240.67830.03560.40610.037*
C13B0.63550 (13)0.3030 (2)0.41053 (7)0.0250 (4)
C14B0.67903 (13)0.4701 (2)0.44983 (7)0.0240 (3)
H1420.74730.49380.44070.029*
C15B0.61383 (15)0.6396 (3)0.42849 (8)0.0307 (4)
H1530.55100.63450.44490.037*
H1540.65160.74970.44520.037*
C16B0.58786 (14)0.6472 (3)0.35839 (8)0.0292 (4)
C17B0.60014 (13)0.5018 (3)0.32233 (8)0.0273 (4)
C18B0.52654 (13)0.2605 (3)0.41605 (8)0.0315 (4)
H1840.48080.35310.39380.047*
H1850.52250.25970.46020.047*
H1860.50680.14180.39760.047*
C19B0.67893 (15)0.1657 (4)0.63078 (9)0.0405 (5)
H1940.69130.15200.67630.061*
H1950.65490.05070.61080.061*
H1960.62760.25930.61750.061*
C22B0.55308 (14)0.7854 (3)0.31462 (8)0.0329 (4)
H2220.53750.90430.32590.039*
C23B0.56032 (14)0.4450 (3)0.20570 (8)0.0317 (4)
C24B0.54753 (15)0.2598 (3)0.20783 (9)0.0367 (5)
H2420.55130.20160.24690.044*
C25B0.52929 (16)0.1581 (4)0.15320 (9)0.0447 (5)
H2520.52130.03070.15430.054*
C26B0.52323 (17)0.2470 (4)0.09777 (9)0.0479 (6)
C27B0.53627 (17)0.4288 (4)0.09393 (9)0.0493 (6)
H2720.53210.48520.05450.059*
C28B0.55582 (16)0.5311 (4)0.14874 (9)0.0418 (5)
H2820.56590.65800.14710.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F26A0.0646 (9)0.0798 (11)0.0369 (7)0.0098 (8)0.0083 (6)0.0217 (7)
O3A0.0476 (8)0.0563 (10)0.0251 (7)0.0006 (8)0.0005 (6)0.0034 (7)
N17A0.0356 (8)0.0235 (8)0.0233 (7)0.0009 (7)0.0064 (6)0.0011 (6)
N20A0.0389 (9)0.0310 (9)0.0265 (7)0.0008 (7)0.0081 (6)0.0062 (7)
N21A0.0387 (9)0.0323 (9)0.0367 (9)0.0016 (7)0.0082 (7)0.0103 (8)
C1A0.0357 (9)0.0252 (9)0.0246 (8)0.0010 (8)0.0051 (7)0.0001 (7)
C2A0.0426 (11)0.0352 (11)0.0258 (8)0.0024 (9)0.0051 (7)0.0045 (8)
C3A0.0350 (10)0.0410 (11)0.0242 (9)0.0044 (9)0.0057 (7)0.0019 (8)
C4A0.0336 (9)0.0375 (11)0.0267 (9)0.0042 (8)0.0050 (7)0.0058 (8)
C5A0.0301 (9)0.0288 (10)0.0280 (9)0.0016 (8)0.0079 (7)0.0057 (8)
C6A0.0442 (11)0.0265 (10)0.0309 (9)0.0047 (8)0.0038 (8)0.0053 (8)
C7A0.0386 (10)0.0290 (10)0.0294 (9)0.0068 (8)0.0039 (7)0.0004 (8)
C8A0.0280 (8)0.0244 (9)0.0251 (8)0.0015 (7)0.0044 (6)0.0012 (7)
C9A0.0278 (8)0.0231 (9)0.0237 (8)0.0005 (7)0.0044 (6)0.0004 (7)
C10A0.0287 (9)0.0259 (9)0.0247 (8)0.0007 (7)0.0043 (7)0.0014 (7)
C11A0.0397 (10)0.0230 (9)0.0245 (8)0.0045 (8)0.0044 (7)0.0006 (7)
C12A0.0378 (9)0.0228 (9)0.0233 (8)0.0009 (8)0.0055 (7)0.0015 (7)
C13A0.0296 (9)0.0234 (9)0.0219 (8)0.0002 (7)0.0048 (6)0.0003 (7)
C14A0.0272 (8)0.0234 (9)0.0261 (8)0.0012 (7)0.0051 (7)0.0000 (7)
C15A0.0343 (9)0.0236 (9)0.0297 (9)0.0004 (7)0.0061 (7)0.0013 (7)
C16A0.0322 (9)0.0260 (9)0.0298 (9)0.0009 (8)0.0072 (7)0.0053 (7)
C17A0.0279 (9)0.0316 (10)0.0262 (8)0.0021 (7)0.0074 (7)0.0034 (8)
C18A0.0302 (9)0.0312 (10)0.0316 (9)0.0001 (8)0.0058 (7)0.0020 (8)
C19A0.0313 (9)0.0355 (11)0.0326 (9)0.0010 (8)0.0084 (7)0.0021 (8)
C22A0.0364 (10)0.0308 (11)0.0359 (10)0.0005 (8)0.0099 (8)0.0053 (8)
C23A0.0306 (9)0.0368 (10)0.0240 (8)0.0015 (8)0.0083 (7)0.0050 (8)
C24A0.0383 (10)0.0413 (12)0.0250 (9)0.0045 (9)0.0087 (7)0.0037 (8)
C25A0.0432 (11)0.0423 (12)0.0340 (10)0.0015 (9)0.0145 (8)0.0034 (9)
C26A0.0394 (11)0.0574 (15)0.0283 (10)0.0090 (10)0.0121 (8)0.0094 (10)
C27A0.0342 (10)0.0634 (16)0.0268 (9)0.0054 (10)0.0052 (8)0.0056 (10)
C28A0.0330 (10)0.0466 (13)0.0307 (9)0.0019 (9)0.0071 (8)0.0082 (9)
F26B0.0783 (10)0.1054 (14)0.0295 (6)0.0167 (10)0.0010 (6)0.0274 (8)
O3B0.0416 (8)0.0449 (9)0.0297 (7)0.0006 (7)0.0075 (6)0.0029 (6)
N17B0.0329 (8)0.0303 (8)0.0194 (7)0.0051 (7)0.0056 (6)0.0021 (6)
N20B0.0338 (8)0.0316 (9)0.0208 (7)0.0018 (7)0.0030 (6)0.0018 (6)
N21B0.0389 (9)0.0321 (9)0.0284 (8)0.0017 (7)0.0016 (6)0.0052 (7)
C1B0.0457 (11)0.0271 (10)0.0272 (9)0.0004 (9)0.0039 (8)0.0001 (8)
C2B0.0453 (11)0.0320 (11)0.0283 (9)0.0023 (9)0.0045 (8)0.0039 (8)
C3B0.0320 (9)0.0363 (11)0.0227 (8)0.0027 (8)0.0041 (7)0.0013 (8)
C4B0.0375 (10)0.0324 (10)0.0238 (9)0.0052 (8)0.0029 (7)0.0043 (8)
C5B0.0332 (9)0.0304 (10)0.0206 (8)0.0032 (8)0.0079 (7)0.0004 (7)
C6B0.0499 (12)0.0322 (11)0.0220 (9)0.0023 (9)0.0022 (8)0.0046 (8)
C7B0.0406 (10)0.0240 (9)0.0239 (8)0.0010 (8)0.0012 (7)0.0012 (7)
C8B0.0293 (8)0.0252 (9)0.0195 (7)0.0019 (7)0.0048 (6)0.0018 (7)
C9B0.0267 (8)0.0253 (9)0.0207 (8)0.0024 (7)0.0033 (6)0.0012 (7)
C10B0.0302 (9)0.0277 (9)0.0214 (8)0.0053 (7)0.0022 (6)0.0013 (7)
C11B0.0398 (10)0.0239 (9)0.0241 (8)0.0011 (8)0.0017 (7)0.0008 (7)
C12B0.0392 (10)0.0272 (9)0.0238 (8)0.0049 (8)0.0013 (7)0.0031 (7)
C13B0.0302 (9)0.0250 (9)0.0190 (8)0.0015 (7)0.0035 (6)0.0022 (7)
C14B0.0291 (8)0.0236 (9)0.0186 (7)0.0010 (7)0.0034 (6)0.0012 (7)
C15B0.0424 (10)0.0250 (9)0.0225 (8)0.0034 (8)0.0021 (7)0.0018 (7)
C16B0.0336 (9)0.0285 (10)0.0238 (8)0.0009 (8)0.0022 (7)0.0005 (7)
C17B0.0275 (8)0.0322 (10)0.0217 (8)0.0008 (7)0.0039 (6)0.0016 (7)
C18B0.0317 (9)0.0340 (10)0.0274 (9)0.0031 (8)0.0032 (7)0.0007 (8)
C19B0.0382 (10)0.0540 (14)0.0288 (9)0.0136 (10)0.0058 (8)0.0065 (10)
C22B0.0395 (10)0.0269 (10)0.0296 (9)0.0005 (8)0.0010 (7)0.0020 (8)
C23B0.0283 (9)0.0455 (12)0.0207 (8)0.0061 (8)0.0040 (7)0.0003 (8)
C24B0.0378 (10)0.0470 (13)0.0244 (9)0.0002 (9)0.0045 (7)0.0055 (9)
C25B0.0429 (11)0.0554 (14)0.0335 (10)0.0011 (11)0.0028 (8)0.0145 (10)
C26B0.0418 (12)0.0766 (19)0.0233 (10)0.0143 (12)0.0018 (8)0.0139 (11)
C27B0.0456 (12)0.080 (2)0.0213 (9)0.0200 (12)0.0056 (8)0.0041 (11)
C28B0.0418 (11)0.0592 (15)0.0247 (9)0.0131 (11)0.0077 (8)0.0071 (10)
Geometric parameters (Å, º) top
F26A—C26A1.368 (2)F26B—C26B1.368 (3)
O3A—C3A1.224 (2)O3B—C3B1.227 (2)
N17A—C17A1.381 (3)N17B—C17B1.389 (2)
N17A—C13A1.491 (2)N17B—C13B1.483 (2)
N17A—H1710.86 (2)N17B—H1720.83 (2)
N20A—C17A1.369 (2)N20B—C17B1.369 (2)
N20A—N21A1.387 (3)N20B—N21B1.376 (2)
N20A—C23A1.415 (3)N20B—C23B1.426 (2)
N21A—C22A1.329 (3)N21B—C22B1.330 (2)
C1A—C2A1.525 (2)C1B—C2B1.526 (3)
C1A—C10A1.543 (3)C1B—C10B1.542 (3)
C1A—H110.9900C1B—H130.9900
C1A—H120.9900C1B—H140.9900
C2A—C3A1.501 (3)C2B—C3B1.499 (3)
C2A—H210.9900C2B—H230.9900
C2A—H220.9900C2B—H240.9900
C3A—C4A1.463 (3)C3B—C4B1.454 (3)
C4A—C5A1.343 (3)C4B—C5B1.346 (3)
C4A—H410.9500C4B—H420.9500
C5A—C6A1.505 (3)C5B—C6B1.500 (3)
C5A—C10A1.518 (2)C5B—C10B1.517 (3)
C6A—C7A1.534 (3)C6B—C7B1.535 (2)
C6A—H610.9900C6B—H630.9900
C6A—H620.9900C6B—H640.9900
C7A—C8A1.534 (2)C7B—C8B1.527 (2)
C7A—H710.9900C7B—H730.9900
C7A—H720.9900C7B—H740.9900
C8A—C9A1.542 (3)C8B—C9B1.546 (2)
C8A—C14A1.546 (2)C8B—C14B1.546 (2)
C8A—H811.0000C8B—H821.0000
C9A—C11A1.533 (2)C9B—C11B1.530 (2)
C9A—C10A1.564 (2)C9B—C10B1.562 (2)
C9A—H911.0000C9B—H921.0000
C10A—C19A1.551 (3)C10B—C19B1.542 (3)
C11A—C12A1.523 (2)C11B—C12B1.522 (2)
C11A—H1110.9900C11B—H1130.9900
C11A—H1120.9900C11B—H1140.9900
C12A—C13A1.522 (3)C12B—C13B1.521 (3)
C12A—H1210.9900C12B—H1230.9900
C12A—H1220.9900C12B—H1240.9900
C13A—C18A1.539 (2)C13B—C18B1.536 (2)
C13A—C14A1.545 (2)C13B—C14B1.549 (2)
C14A—C15A1.544 (3)C14B—C15B1.547 (3)
C14A—H1411.0000C14B—H1421.0000
C15A—C16A1.503 (2)C15B—C16B1.502 (2)
C15A—H1510.9900C15B—H1530.9900
C15A—H1520.9900C15B—H1540.9900
C16A—C17A1.372 (3)C16B—C17B1.365 (3)
C16A—C22A1.405 (3)C16B—C22B1.412 (3)
C18A—H1810.9800C18B—H1840.9800
C18A—H1820.9800C18B—H1850.9800
C18A—H1830.9800C18B—H1860.9800
C19A—H1910.9800C19B—H1940.9800
C19A—H1920.9800C19B—H1950.9800
C19A—H1930.9800C19B—H1960.9800
C22A—H2210.9500C22B—H2220.9500
C23A—C24A1.383 (3)C23B—C24B1.383 (3)
C23A—C28A1.394 (3)C23B—C28B1.390 (3)
C24A—C25A1.389 (3)C24B—C25B1.390 (3)
C24A—H2410.9500C24B—H2420.9500
C25A—C26A1.371 (3)C25B—C26B1.367 (3)
C25A—H2510.9500C25B—H2520.9500
C26A—C27A1.370 (4)C26B—C27B1.361 (4)
C27A—C28A1.388 (3)C27B—C28B1.396 (3)
C27A—H2710.9500C27B—H2720.9500
C28A—H2810.9500C28B—H2820.9500
C17A—N17A—C13A112.53 (15)C17B—N17B—C13B112.88 (14)
C17A—N17A—H171113.6 (15)C17B—N17B—H172114.9 (18)
C13A—N17A—H171111.5 (14)C13B—N17B—H172111.8 (15)
C17A—N20A—N21A110.68 (16)C17B—N20B—N21B110.66 (16)
C17A—N20A—C23A128.70 (17)C17B—N20B—C23B129.84 (17)
N21A—N20A—C23A120.30 (15)N21B—N20B—C23B118.94 (15)
C22A—N21A—N20A103.94 (16)C22B—N21B—N20B104.35 (16)
C2A—C1A—C10A113.93 (16)C2B—C1B—C10B113.45 (17)
C2A—C1A—H11108.8C2B—C1B—H13108.9
C10A—C1A—H11108.8C10B—C1B—H13108.9
C2A—C1A—H12108.8C2B—C1B—H14108.9
C10A—C1A—H12108.8C10B—C1B—H14108.9
H11—C1A—H12107.7H13—C1B—H14107.7
C3A—C2A—C1A111.53 (16)C3B—C2B—C1B111.35 (17)
C3A—C2A—H21109.3C3B—C2B—H23109.4
C1A—C2A—H21109.3C1B—C2B—H23109.4
C3A—C2A—H22109.3C3B—C2B—H24109.4
C1A—C2A—H22109.3C1B—C2B—H24109.4
H21—C2A—H22108.0H23—C2B—H24108.0
O3A—C3A—C4A121.75 (19)O3B—C3B—C4B122.35 (18)
O3A—C3A—C2A121.7 (2)O3B—C3B—C2B120.44 (18)
C4A—C3A—C2A116.47 (15)C4B—C3B—C2B117.13 (14)
C5A—C4A—C3A123.92 (18)C5B—C4B—C3B123.81 (18)
C5A—C4A—H41118.0C5B—C4B—H42118.1
C3A—C4A—H41118.0C3B—C4B—H42118.1
C4A—C5A—C6A120.43 (17)C4B—C5B—C6B120.96 (17)
C4A—C5A—C10A122.90 (18)C4B—C5B—C10B122.44 (18)
C6A—C5A—C10A116.54 (15)C6B—C5B—C10B116.43 (14)
C5A—C6A—C7A113.47 (15)C5B—C6B—C7B113.87 (16)
C5A—C6A—H61108.9C5B—C6B—H63108.8
C7A—C6A—H61108.9C7B—C6B—H63108.8
C5A—C6A—H62108.9C5B—C6B—H64108.8
C7A—C6A—H62108.9C7B—C6B—H64108.8
H61—C6A—H62107.7H63—C6B—H64107.7
C8A—C7A—C6A111.92 (15)C8B—C7B—C6B112.15 (16)
C8A—C7A—H71109.2C8B—C7B—H73109.2
C6A—C7A—H71109.2C6B—C7B—H73109.2
C8A—C7A—H72109.2C8B—C7B—H74109.2
C6A—C7A—H72109.2C6B—C7B—H74109.2
H71—C7A—H72107.9H73—C7B—H74107.9
C7A—C8A—C9A108.65 (14)C7B—C8B—C9B109.16 (13)
C7A—C8A—C14A111.55 (14)C7B—C8B—C14B111.62 (14)
C9A—C8A—C14A112.83 (14)C9B—C8B—C14B111.25 (14)
C7A—C8A—H81107.9C7B—C8B—H82108.2
C9A—C8A—H81107.9C9B—C8B—H82108.2
C14A—C8A—H81107.9C14B—C8B—H82108.2
C11A—C9A—C8A112.88 (13)C11B—C9B—C8B111.58 (13)
C11A—C9A—C10A112.13 (14)C11B—C9B—C10B111.95 (15)
C8A—C9A—C10A112.77 (14)C8B—C9B—C10B113.71 (14)
C11A—C9A—H91106.1C11B—C9B—H92106.3
C8A—C9A—H91106.1C8B—C9B—H92106.3
C10A—C9A—H91106.1C10B—C9B—H92106.3
C5A—C10A—C1A109.59 (14)C5B—C10B—C1B109.51 (14)
C5A—C10A—C19A107.30 (15)C5B—C10B—C19B107.63 (16)
C1A—C10A—C19A110.71 (16)C1B—C10B—C19B110.07 (17)
C5A—C10A—C9A109.51 (14)C5B—C10B—C9B109.63 (15)
C1A—C10A—C9A108.00 (14)C1B—C10B—C9B108.40 (15)
C19A—C10A—C9A111.72 (14)C19B—C10B—C9B111.58 (14)
C12A—C11A—C9A111.57 (15)C12B—C11B—C9B111.37 (15)
C12A—C11A—H111109.3C12B—C11B—H113109.4
C9A—C11A—H111109.3C9B—C11B—H113109.4
C12A—C11A—H112109.3C12B—C11B—H114109.4
C9A—C11A—H112109.3C9B—C11B—H114109.4
H111—C11A—H112108.0H113—C11B—H114108.0
C13A—C12A—C11A111.71 (15)C13B—C12B—C11B112.23 (15)
C13A—C12A—H121109.3C13B—C12B—H123109.2
C11A—C12A—H121109.3C11B—C12B—H123109.2
C13A—C12A—H122109.3C13B—C12B—H124109.2
C11A—C12A—H122109.3C11B—C12B—H124109.2
H121—C12A—H122107.9H123—C12B—H124107.9
N17A—C13A—C12A105.86 (14)N17B—C13B—C12B106.02 (14)
N17A—C13A—C18A109.22 (14)N17B—C13B—C18B106.54 (13)
C12A—C13A—C18A111.15 (16)C12B—C13B—C18B111.66 (16)
N17A—C13A—C14A108.69 (14)N17B—C13B—C14B111.76 (14)
C12A—C13A—C14A109.36 (13)C12B—C13B—C14B108.49 (13)
C18A—C13A—C14A112.32 (15)C18B—C13B—C14B112.21 (14)
C15A—C14A—C13A111.79 (14)C8B—C14B—C15B112.89 (14)
C15A—C14A—C8A111.73 (14)C8B—C14B—C13B112.56 (14)
C13A—C14A—C8A111.34 (14)C15B—C14B—C13B110.67 (13)
C15A—C14A—H141107.2C8B—C14B—H142106.8
C13A—C14A—H141107.2C15B—C14B—H142106.8
C8A—C14A—H141107.2C13B—C14B—H142106.8
C16A—C15A—C14A109.77 (15)C16B—C15B—C14B109.57 (15)
C16A—C15A—H151109.7C16B—C15B—H153109.8
C14A—C15A—H151109.7C14B—C15B—H153109.8
C16A—C15A—H152109.7C16B—C15B—H154109.8
C14A—C15A—H152109.7C14B—C15B—H154109.8
H151—C15A—H152108.2H153—C15B—H154108.2
C17A—C16A—C22A104.18 (16)C17B—C16B—C22B103.98 (15)
C17A—C16A—C15A121.30 (16)C17B—C16B—C15B122.04 (17)
C22A—C16A—C15A134.51 (19)C22B—C16B—C15B133.92 (18)
N20A—C17A—C16A108.00 (17)C16B—C17B—N20B108.30 (16)
N20A—C17A—N17A125.27 (17)C16B—C17B—N17B126.87 (15)
C16A—C17A—N17A126.72 (15)N20B—C17B—N17B124.82 (16)
C13A—C18A—H181109.5C13B—C18B—H184109.5
C13A—C18A—H182109.5C13B—C18B—H185109.5
H181—C18A—H182109.5H184—C18B—H185109.5
C13A—C18A—H183109.5C13B—C18B—H186109.5
H181—C18A—H183109.5H184—C18B—H186109.5
H182—C18A—H183109.5H185—C18B—H186109.5
C10A—C19A—H191109.5C10B—C19B—H194109.5
C10A—C19A—H192109.5C10B—C19B—H195109.5
H191—C19A—H192109.5H194—C19B—H195109.5
C10A—C19A—H193109.5C10B—C19B—H196109.5
H191—C19A—H193109.5H194—C19B—H196109.5
H192—C19A—H193109.5H195—C19B—H196109.5
N21A—C22A—C16A113.19 (19)N21B—C22B—C16B112.70 (18)
N21A—C22A—H221123.4N21B—C22B—H222123.7
C16A—C22A—H221123.4C16B—C22B—H222123.7
C24A—C23A—C28A120.71 (19)C24B—C23B—C28B120.1 (2)
C24A—C23A—N20A120.11 (17)C24B—C23B—N20B121.18 (18)
C28A—C23A—N20A119.18 (19)C28B—C23B—N20B118.6 (2)
C23A—C24A—C25A120.09 (18)C23B—C24B—C25B120.5 (2)
C23A—C24A—H241120.0C23B—C24B—H242119.7
C25A—C24A—H241120.0C25B—C24B—H242119.7
C26A—C25A—C24A117.9 (2)C26B—C25B—C24B118.0 (3)
C26A—C25A—H251121.0C26B—C25B—H252121.0
C24A—C25A—H251121.0C24B—C25B—H252121.0
F26A—C26A—C27A118.26 (19)C27B—C26B—C25B123.1 (2)
F26A—C26A—C25A118.4 (2)C27B—C26B—F26B118.4 (2)
C27A—C26A—C25A123.4 (2)C25B—C26B—F26B118.6 (3)
C26A—C27A—C28A118.68 (19)C26B—C27B—C28B119.1 (2)
C26A—C27A—H271120.7C26B—C27B—H272120.5
C28A—C27A—H271120.7C28B—C27B—H272120.5
C27A—C28A—C23A119.2 (2)C23B—C28B—C27B119.1 (3)
C27A—C28A—H281120.4C23B—C28B—H282120.4
C23A—C28A—H281120.4C27B—C28B—H282120.4
C17A—N20A—N21A—C22A0.8 (2)C23B—N20B—N21B—C22B171.66 (16)
C23A—N20A—N21A—C22A174.76 (16)C10B—C1B—C2B—C3B53.8 (2)
C10A—C1A—C2A—C3A53.9 (2)C1B—C2B—C3B—O3B154.23 (19)
C1A—C2A—C3A—O3A151.08 (19)C1B—C2B—C3B—C4B29.0 (2)
C1A—C2A—C3A—C4A31.8 (2)O3B—C3B—C4B—C5B176.91 (19)
O3A—C3A—C4A—C5A178.2 (2)C2B—C3B—C4B—C5B0.2 (3)
C2A—C3A—C4A—C5A4.6 (3)C3B—C4B—C5B—C6B170.37 (18)
C3A—C4A—C5A—C6A173.90 (17)C3B—C4B—C5B—C10B4.8 (3)
C3A—C4A—C5A—C10A1.9 (3)C4B—C5B—C6B—C7B137.31 (19)
C4A—C5A—C6A—C7A137.21 (18)C10B—C5B—C6B—C7B47.3 (2)
C10A—C5A—C6A—C7A46.7 (2)C5B—C6B—C7B—C8B50.7 (2)
C5A—C6A—C7A—C8A50.8 (2)C6B—C7B—C8B—C9B54.8 (2)
C6A—C7A—C8A—C9A56.7 (2)C6B—C7B—C8B—C14B178.24 (15)
C6A—C7A—C8A—C14A178.30 (15)C7B—C8B—C9B—C11B175.07 (14)
C7A—C8A—C9A—C11A172.29 (15)C14B—C8B—C9B—C11B51.46 (19)
C14A—C8A—C9A—C11A48.0 (2)C7B—C8B—C9B—C10B57.14 (18)
C7A—C8A—C9A—C10A59.36 (19)C14B—C8B—C9B—C10B179.24 (14)
C14A—C8A—C9A—C10A176.40 (14)C4B—C5B—C10B—C1B19.2 (2)
C4A—C5A—C10A—C1A18.8 (2)C6B—C5B—C10B—C1B165.46 (16)
C6A—C5A—C10A—C1A165.18 (16)C4B—C5B—C10B—C19B100.4 (2)
C4A—C5A—C10A—C19A101.4 (2)C6B—C5B—C10B—C19B74.9 (2)
C6A—C5A—C10A—C19A74.56 (19)C4B—C5B—C10B—C9B138.01 (18)
C4A—C5A—C10A—C9A137.13 (18)C6B—C5B—C10B—C9B46.6 (2)
C6A—C5A—C10A—C9A46.9 (2)C2B—C1B—C10B—C5B48.1 (2)
C2A—C1A—C10A—C5A46.4 (2)C2B—C1B—C10B—C19B70.1 (2)
C2A—C1A—C10A—C19A71.79 (19)C2B—C1B—C10B—C9B167.65 (16)
C2A—C1A—C10A—C9A165.60 (15)C11B—C9B—C10B—C5B179.65 (15)
C11A—C9A—C10A—C5A177.67 (15)C8B—C9B—C10B—C5B52.05 (19)
C8A—C9A—C10A—C5A53.58 (19)C11B—C9B—C10B—C1B60.85 (19)
C11A—C9A—C10A—C1A58.39 (19)C8B—C9B—C10B—C1B171.55 (14)
C8A—C9A—C10A—C1A172.87 (14)C11B—C9B—C10B—C19B60.5 (2)
C11A—C9A—C10A—C19A63.6 (2)C8B—C9B—C10B—C19B67.1 (2)
C8A—C9A—C10A—C19A65.15 (19)C8B—C9B—C11B—C12B53.9 (2)
C8A—C9A—C11A—C12A50.3 (2)C10B—C9B—C11B—C12B177.40 (15)
C10A—C9A—C11A—C12A178.99 (15)C9B—C11B—C12B—C13B58.5 (2)
C9A—C11A—C12A—C13A57.1 (2)C17B—N17B—C13B—C12B160.30 (15)
C17A—N17A—C13A—C12A166.57 (15)C17B—N17B—C13B—C18B80.63 (18)
C17A—N17A—C13A—C18A73.7 (2)C17B—N17B—C13B—C14B42.3 (2)
C17A—N17A—C13A—C14A49.2 (2)C11B—C12B—C13B—N17B178.53 (15)
C11A—C12A—C13A—N17A177.15 (14)C11B—C12B—C13B—C18B65.83 (19)
C11A—C12A—C13A—C18A64.36 (18)C11B—C12B—C13B—C14B58.3 (2)
C11A—C12A—C13A—C14A60.2 (2)C7B—C8B—C14B—C15B58.2 (2)
N17A—C13A—C14A—C15A62.20 (19)C9B—C8B—C14B—C15B179.62 (14)
C12A—C13A—C14A—C15A177.34 (15)C7B—C8B—C14B—C13B175.64 (15)
C18A—C13A—C14A—C15A58.77 (19)C9B—C8B—C14B—C13B53.44 (18)
N17A—C13A—C14A—C8A172.04 (14)N17B—C13B—C14B—C8B172.58 (14)
C12A—C13A—C14A—C8A56.91 (19)C12B—C13B—C14B—C8B56.03 (19)
C18A—C13A—C14A—C8A66.98 (18)C18B—C13B—C14B—C8B67.81 (18)
C7A—C8A—C14A—C15A60.1 (2)N17B—C13B—C14B—C15B60.06 (19)
C9A—C8A—C14A—C15A177.24 (14)C12B—C13B—C14B—C15B176.60 (14)
C7A—C8A—C14A—C13A174.10 (15)C18B—C13B—C14B—C15B59.56 (19)
C9A—C8A—C14A—C13A51.46 (19)C8B—C14B—C15B—C16B171.07 (15)
C13A—C14A—C15A—C16A42.4 (2)C13B—C14B—C15B—C16B43.9 (2)
C8A—C14A—C15A—C16A167.90 (14)C14B—C15B—C16B—C17B14.7 (3)
C14A—C15A—C16A—C17A12.5 (2)C14B—C15B—C16B—C22B162.2 (2)
C14A—C15A—C16A—C22A168.0 (2)C22B—C16B—C17B—N20B0.2 (2)
N21A—N20A—C17A—C16A0.6 (2)C15B—C16B—C17B—N20B177.88 (17)
C23A—N20A—C17A—C16A173.89 (18)C22B—C16B—C17B—N17B179.72 (17)
N21A—N20A—C17A—N17A179.65 (18)C15B—C16B—C17B—N17B2.6 (3)
C23A—N20A—C17A—N17A7.0 (3)N21B—N20B—C17B—C16B0.5 (2)
C22A—C16A—C17A—N20A0.1 (2)C23B—N20B—C17B—C16B170.63 (18)
C15A—C16A—C17A—N20A179.76 (16)N21B—N20B—C17B—N17B179.97 (17)
C22A—C16A—C17A—N17A179.16 (19)C23B—N20B—C17B—N17B8.9 (3)
C15A—C16A—C17A—N17A1.2 (3)C13B—N17B—C17B—C16B11.7 (3)
C13A—N17A—C17A—N20A160.51 (16)C13B—N17B—C17B—N20B167.76 (16)
C13A—N17A—C17A—C16A20.6 (3)N20B—N21B—C22B—C16B0.4 (2)
N20A—N21A—C22A—C16A0.7 (2)C17B—C16B—C22B—N21B0.1 (2)
C17A—C16A—C22A—N21A0.4 (2)C15B—C16B—C22B—N21B177.10 (19)
C15A—C16A—C22A—N21A179.17 (19)C17B—N20B—C23B—C24B17.4 (3)
C17A—N20A—C23A—C24A42.9 (3)N21B—N20B—C23B—C24B153.09 (19)
N21A—N20A—C23A—C24A144.39 (19)C17B—N20B—C23B—C28B165.45 (18)
C17A—N20A—C23A—C28A136.8 (2)N21B—N20B—C23B—C28B24.0 (3)
N21A—N20A—C23A—C28A35.9 (3)C28B—C23B—C24B—C25B0.5 (3)
C28A—C23A—C24A—C25A1.9 (3)N20B—C23B—C24B—C25B176.54 (17)
N20A—C23A—C24A—C25A177.79 (18)C23B—C24B—C25B—C26B0.8 (3)
C23A—C24A—C25A—C26A2.5 (3)C24B—C25B—C26B—C27B1.4 (3)
C24A—C25A—C26A—F26A179.17 (18)C24B—C25B—C26B—F26B178.54 (18)
C24A—C25A—C26A—C27A1.3 (3)C25B—C26B—C27B—C28B0.6 (4)
F26A—C26A—C27A—C28A179.01 (18)F26B—C26B—C27B—C28B179.29 (17)
C25A—C26A—C27A—C28A0.5 (3)C24B—C23B—C28B—C27B1.3 (3)
C26A—C27A—C28A—C23A1.2 (3)N20B—C23B—C28B—C27B175.86 (18)
C24A—C23A—C28A—C27A0.0 (3)C26B—C27B—C28B—C23B0.7 (3)
N20A—C23A—C28A—C27A179.64 (17)C19A—C10A—C13A—C18A1.31 (15)
C17B—N20B—N21B—C22B0.6 (2)C19B—C10B—C13B—C18B1.88 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24B—H242···N17B0.952.362.990 (2)123
N17A—H171···O3Bi0.86 (2)2.16 (2)2.975 (2)158.6 (19)
N17B—H172···N21Aii0.83 (2)2.54 (2)3.281 (2)149 (2)
C4A—H41···N21Biii0.952.613.467 (2)151
C27A—H271···F26Ai0.952.413.320 (2)161
C27B—H272···F26Biii0.952.423.365 (3)171
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x, y1, z; (iii) x+1, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC26H30FN3O
Mr419.53
Crystal system, space groupMonoclinic, P21
Temperature (K)160
a, b, c (Å)13.5243 (2), 7.3983 (1), 21.8934 (3)
β (°) 102.1562 (8)
V3)2141.47 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.28 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
64206, 6714, 5595
Rint0.055
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.100, 1.02
No. of reflections6704
No. of parameters571
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.19

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24B—H242···N17B0.952.362.990 (2)123
N17A—H171···O3Bi0.86 (2)2.16 (2)2.975 (2)158.6 (19)
N17B—H172···N21Aii0.83 (2)2.54 (2)3.281 (2)149 (2)
C4A—H41···N21Biii0.952.613.467 (2)151
C27A—H271···F26Ai0.952.413.320 (2)161
C27B—H272···F26Biii0.952.423.365 (3)171
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x, y1, z; (iii) x+1, y+1/2, z.
 

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