Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113024943/fn3154sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113024943/fn3154Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113024943/fn3154Isup3.cml |
CCDC reference: 969477
Substituted pyrazoles have been the subject of numerous reports concerning their biological activity and potential pharmacological properties. In fact, these compounds are an important class of bioactive targets in the pharmaceutical industry that includes blockbuster drugs such as Viagra (Terrett et al., 1996), Celebrex (Penning et al., 1997) etc. In addition, pyrazoles are attractive from a pharmacological point of view as analgesic, antiparasitic, anti-anxiety, antimicrobial, antipyretic and anti-inflammatory drugs (Elguero et al., 2002), and some related derivatives have been found to be potent PDE4B inhibitors (Card et al., 2005). Pyrazole compounds are also of interest in coordination chemistry: since the heterocyclic nuclei may coordinate directly via one or both vicinal N atoms, they have been used as quite effective ligands for obtaining transition metal complexes (Rojas et al., 2004).
In the last few years, we have reported the synthesis and molecular structure of two closely related compounds with a common pyrazole-centred core (hereinafter `B') flanked on both sides by a phenyl and a diazenyl-pentafluorophenyl group, viz. 3,5-dimethyl-1-(4-nitrophenyl)-4-[(E)-(2,3,4,5,6-pentafluorophenyl)diazenyl]-1H-pyrazole, (II) (Bustos, Sánchez, Schott et al., 2007) and 3,5-dimethyl-1-(4-nitrophenyl)-4-[(E)-(2,3,4,5,6-pentafluorophenyl)diazenyl]-1H-pyrazole, (III) (Alvarez Thon et al., 2013).
Surprisingly, a search of the Cambridge Structural Database (CSD, Version?; Allen, 2002) confirmed these to be the only structures based on such a core which have been reported so far, so we decided to continue investigating the structural possibilities of this family. As a result, we present here the structure of a new member of the group, the title compound (Z)-3-methyl-4-[2-(4-methylphenyl)hydrazinylidene]-1-(perfluorophenyl)-1H-pyrazol-5(4H)-one, (I), and compare it with the previously reported analogues.
Ethyl (Z)-3-oxo-2-(2-p-tolylhydrazinilydene)butanoate was prepared according to the method recommended in the literature (Yao, 1964; Bertolasi et al., 1999; Bustos, Sánchez, Martínez et al., 2007; Bustos et al., 2009) and recrystallized from ethanol. Solvents (EtOH, CHCl3, CDCl3 and glacial acetic acid) were provided by Merck and perfluorophenylhydrazine by Aldrich.
Ethyl (Z)-3-oxo-2-(2-p-tolylhydrazinilydene)butanoate (2.48 g, 10 mmol), perfluorophenylhydrazine (2.04 g, 10 mmol, 97%), glacial acetic acid (5 ml) and ethanol (30 ml) were added to a round-bottomed flask. The mixture was stirred and heated at reflux near the boiling point, and a yellow–orange solid precipitate was formed after 36 h. The reaction mixture was cooled at 263 K for 2 h, and the product was then filtered off by suction at room temperature, washed with an abundant quantity of water (500 ml) and dried in a vacuum oven at 313 K for 12 h. Single crystals of (I) suitable for diffraction studies were obtained by recrystallization from an ethanol–water (1:1 v/v) mixture (yield 70.6%; m.p. 395–396 K). Analysis, calculated (%) for C17H11F5N4O: C 53.41, H 2.90, N 14.66; found (%): C 53.26, H 2.88, N 14.88.
H atoms were originally found in a difference Fourier map, but were treated differently. N-bound H atoms were refined with a restrained N—H distance of 0.85 (1) Å, while C-bound H atoms were repositioned in their expected positions and thereinafter allowed to ride, with C—H = 0.96 (methyl) or 0.93 Å (aromatic). Methyl groups were allowed to rotate around their C—C bond. For all H atoms, Uiso(H) = 1.5Ueq(H). [Rephrasing OK?]
The title compound, (I), crystallizes with two independent molecules in the asymmetric unit [hereinafter (Ia) and (Ib); Fig 1], linked by a diversity of noncovalent interactions into a strongly bound dimer which should be considered the elemental building block of the crystal structure.
The two independent units are extremely similar regarding interatomic distances and angles. This similarity can be best assessed in graphical terms through the superposition of the two independent molecules, shown in Fig. 2(a). It is apparent that the only significant difference is found in the C8/N3/N4/C12/C13/C17 region, a fact confirmed by a brief review of some relevant torsion angles, given in the order (Ia)/(Ib): C8—N3—N4—C12 = -178.65 (14)/-173.28 (14)°, N3—N4—C12—C17 = 166.92 (16)/160.32 (16)° and N3—N4—C12—C13 = -13.1 (3)/-18.6 (2)°.
These molecular similarities have, in fact, a deeper significance. A PLATON run (Spek, 2009) using the quaternion algorithm proposed by Mackay (1984) disclosed a striking noncrystallographic twofold pseudorotation relating the two independent units, with a mean r.m.s. atom misfit of 0.14 Å. When pseudosymmetry-related bond lengths and angles are compared, r.m.s. misfits are also extremely low, viz. 0.0063 Å and 0.570°, respectively.
A quick comparison of (I) with its two predecessors, (II) and (III), can be seen in Scheme 1. It is apparent that the main differences appear in the imidazole group and its neighbourhood, through the replacement of one methyl substituent in (II) and (III) with an oxo group in (I), and the protonation of atom N3, with the consequent reorganization of the electron distribution. This `reshuffling' is clearly revealed in some relevant bond distances (Table 2) and in the supramolecular organization (see below).
Pushing comparisons a bit further, Fig 2(b) shows a comparative overlap of all four molecular units, viz. (Ia), (Ib), (II) and (III), where only the pyrazole rings were used for fitting purposes. It can be seen that the pentafluorophenyl rings present a marked preferred orientation, viz. (Ia), (Ib) and (II) versus (III), while on the phenyl side the preferences are evenly split, the N3—N4 bond being cis to the C6F5 group in (Ia) and (Ib) but trans in (II) and (III).
Similarly, the appearance of the N—H group in (I) renders the supramolecular organization quite different from those in (II) and (III). Fig. 1 shows the way in which the dimers are built up; the main link is the central R42(4) loop (for nomenclature, see Bernstein et al., 1995) involving all four N—H···O hydrogen bonds presented in Table 3, complemented by the two lateral quasi-symmetrical Cg···Cg interactions presented in Table 4. These well connected dimers are in turn joined into a tetrameric unit by a short F···F contact [F2a···F2ai = 2.7955 (18) Å and C2a—F2a···.F2ai = 138.24 (11)°; symmetry code: (i) -x + 1, -y + 1, -z + 1; Fig. 3). This interaction could be considered medium strength: a search of the CSD disclosed about 21500 F···F contacts in the range 2.40–2.95Å, and the present one lies in the 40th lower percentile. At this stage it is interesting to comment on the characteristics of C—F···F—C interactions which, according to their geometric disposition, have historically been divided into type-I and type-II (see Scheme 2); the case analysed herein, developed around an inversion centre, corresponds to the first type. Even if only type-II contacts had been originally ascribed a stabilizing effect, further studies began disclosing a stabilizing character in many type-I cases, in particular those already found in structures (II) and (III). For further details on the subject, see Baker et al. (2012, and references therein).
The interactions described so far are all the middle-strength noncovalent ones in the structure. There is a weaker C—Hmethyl···F contact (Table 3, fifth entry, and Fig 4a, labelled A) feebly connecting tetramers into broad two-dimensional structures parallel to (101). From Fig. 4(b) it can be seen that the substructure could also be topologically described as made up of two parallel thin planes (with a rather weak internal connection, A bonds) linked by the stronger F···F interaction (labelled B).
The rather unattractive supramolecular organization of (I) compared with the much richer ones of (II) and (III) allows a brief comment about the role of the oxo group in the structure. Its presence allows for the pairing of neighbouring molecules into strongly linked dimers. But, at the same time, the very closeness of these structures somehow `shields' the C—F groups from effective intermolecular interactions, to the extent that only one C—F···F—C bond appears in the structure. On the other hand, its role is relevant in that it is the sole linkage in the formation of the tetramer, thus providing a further example that type-I C—F···F—C interactions should be given due consideration as effective synthons in supramolecular organization.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
C17H11F5N4O | F(000) = 1552 |
Mr = 382.30 | Dx = 1.480 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 999 reflections |
a = 11.6678 (12) Å | θ = 2.2–26.3° |
b = 16.6283 (17) Å | µ = 0.13 mm−1 |
c = 17.8362 (18) Å | T = 297 K |
β = 97.368 (2)° | Polyhedron, orange |
V = 3431.9 (6) Å3 | 0.32 × 0.22 × 0.22 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 7711 independent reflections |
Radiation source: fine-focus sealed tube | 4062 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
CCD rotation images, thin slices scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS in SAINT-NT; Bruker, 2002) | h = −14→15 |
Tmin = 0.96, Tmax = 0.98 | k = −21→21 |
28507 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0667P)2] where P = (Fo2 + 2Fc2)/3 |
7711 reflections | (Δ/σ)max < 0.001 |
495 parameters | Δρmax = 0.18 e Å−3 |
2 restraints | Δρmin = −0.12 e Å−3 |
C17H11F5N4O | V = 3431.9 (6) Å3 |
Mr = 382.30 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.6678 (12) Å | µ = 0.13 mm−1 |
b = 16.6283 (17) Å | T = 297 K |
c = 17.8362 (18) Å | 0.32 × 0.22 × 0.22 mm |
β = 97.368 (2)° |
Bruker SMART CCD area-detector diffractometer | 7711 independent reflections |
Absorption correction: multi-scan (SADABS in SAINT-NT; Bruker, 2002) | 4062 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.98 | Rint = 0.032 |
28507 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 2 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 0.18 e Å−3 |
7711 reflections | Δρmin = −0.12 e Å−3 |
495 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
F1A | 0.50190 (10) | 0.43994 (7) | 0.35505 (6) | 0.0917 (3) | |
F2A | 0.43557 (10) | 0.42890 (8) | 0.49344 (6) | 0.1065 (4) | |
F3A | 0.29988 (11) | 0.30759 (10) | 0.52667 (7) | 0.1289 (5) | |
F4A | 0.22606 (12) | 0.19672 (9) | 0.42029 (9) | 0.1425 (6) | |
F5A | 0.29140 (11) | 0.20694 (7) | 0.28119 (8) | 0.1140 (4) | |
O10A | 0.34010 (10) | 0.44646 (7) | 0.19669 (6) | 0.0741 (3) | |
N1A | 0.43248 (13) | 0.32949 (9) | 0.24210 (7) | 0.0716 (4) | |
N2A | 0.49379 (14) | 0.26536 (10) | 0.21374 (8) | 0.0848 (5) | |
N3A | 0.42135 (12) | 0.38300 (9) | 0.05095 (7) | 0.0666 (4) | |
N4A | 0.35879 (13) | 0.44722 (9) | 0.03982 (8) | 0.0656 (4) | |
H4A | 0.3228 (13) | 0.4657 (10) | 0.0755 (8) | 0.081 (6)* | |
C1A | 0.43441 (15) | 0.37910 (11) | 0.37010 (9) | 0.0666 (4) | |
C2A | 0.40150 (16) | 0.37404 (13) | 0.44071 (10) | 0.0753 (5) | |
C3A | 0.33317 (18) | 0.31226 (16) | 0.45762 (12) | 0.0858 (6) | |
C4A | 0.29621 (17) | 0.25670 (14) | 0.40428 (15) | 0.0903 (6) | |
C5A | 0.32922 (16) | 0.26167 (12) | 0.33346 (12) | 0.0770 (5) | |
C6A | 0.39927 (15) | 0.32322 (11) | 0.31471 (9) | 0.0644 (4) | |
C7A | 0.39526 (14) | 0.38548 (11) | 0.18767 (9) | 0.0623 (4) | |
C8A | 0.43722 (14) | 0.35375 (11) | 0.12069 (9) | 0.0648 (4) | |
C9A | 0.49699 (17) | 0.28104 (12) | 0.14296 (10) | 0.0782 (5) | |
C11A | 0.5564 (2) | 0.22680 (15) | 0.09328 (12) | 0.1145 (8) | |
H11A | 0.5695 | 0.1753 | 0.1172 | 0.172* | |
H11B | 0.6291 | 0.2500 | 0.0851 | 0.172* | |
H11C | 0.5088 | 0.2202 | 0.0456 | 0.172* | |
C12A | 0.33487 (14) | 0.48203 (10) | −0.03302 (9) | 0.0609 (4) | |
C13A | 0.39452 (14) | 0.45960 (10) | −0.09166 (9) | 0.0656 (4) | |
H13A | 0.4524 | 0.4209 | −0.0843 | 0.079* | |
C14A | 0.36682 (16) | 0.49568 (12) | −0.16176 (10) | 0.0752 (5) | |
H14A | 0.4069 | 0.4808 | −0.2014 | 0.090* | |
C15A | 0.28118 (17) | 0.55320 (12) | −0.17412 (10) | 0.0772 (5) | |
C16A | 0.22477 (17) | 0.57414 (13) | −0.11347 (11) | 0.0863 (6) | |
H16A | 0.1675 | 0.6133 | −0.1202 | 0.104* | |
C17A | 0.25025 (17) | 0.53920 (12) | −0.04378 (10) | 0.0783 (5) | |
H17A | 0.2103 | 0.5543 | −0.0041 | 0.094* | |
C18A | 0.2504 (2) | 0.59211 (17) | −0.25086 (11) | 0.1185 (9) | |
H18A | 0.1707 | 0.6080 | −0.2569 | 0.178* | |
H18B | 0.2629 | 0.5544 | −0.2897 | 0.178* | |
H18C | 0.2982 | 0.6386 | −0.2546 | 0.178* | |
F1B | −0.03496 (9) | 0.39618 (7) | −0.06906 (6) | 0.0978 (4) | |
F2B | 0.03163 (12) | 0.41981 (8) | −0.20683 (7) | 0.1132 (4) | |
F3B | 0.22147 (12) | 0.34489 (8) | −0.24379 (6) | 0.1158 (5) | |
F4B | 0.34820 (11) | 0.24954 (8) | −0.14265 (8) | 0.1182 (5) | |
F5B | 0.28452 (10) | 0.22800 (7) | −0.00459 (6) | 0.0970 (4) | |
O10B | 0.11880 (11) | 0.43062 (7) | 0.08770 (6) | 0.0720 (3) | |
N1B | 0.09168 (13) | 0.30130 (8) | 0.03918 (8) | 0.0702 (4) | |
N2B | 0.06695 (14) | 0.22392 (8) | 0.06571 (9) | 0.0775 (4) | |
N3B | 0.07544 (11) | 0.34048 (9) | 0.23068 (7) | 0.0622 (4) | |
N4B | 0.10288 (12) | 0.41561 (9) | 0.24342 (8) | 0.0643 (4) | |
H4B | 0.1231 (15) | 0.4463 (9) | 0.2088 (8) | 0.088 (6)* | |
C1B | 0.05981 (15) | 0.35999 (10) | −0.08648 (10) | 0.0667 (5) | |
C2B | 0.09267 (18) | 0.37214 (11) | −0.15683 (10) | 0.0740 (5) | |
C3B | 0.18872 (19) | 0.33346 (13) | −0.17572 (10) | 0.0780 (5) | |
C4B | 0.25151 (17) | 0.28452 (12) | −0.12438 (12) | 0.0770 (5) | |
C5B | 0.21860 (16) | 0.27375 (10) | −0.05463 (10) | 0.0669 (5) | |
C6B | 0.12209 (15) | 0.31098 (10) | −0.03395 (9) | 0.0606 (4) | |
C7B | 0.09704 (14) | 0.35906 (10) | 0.09474 (9) | 0.0603 (4) | |
C8B | 0.07152 (14) | 0.31423 (10) | 0.16034 (9) | 0.0610 (4) | |
C9B | 0.05312 (15) | 0.23266 (11) | 0.13663 (10) | 0.0703 (5) | |
C11B | 0.0229 (2) | 0.16308 (12) | 0.18273 (11) | 0.0996 (7) | |
H11D | −0.0516 | 0.1719 | 0.1987 | 0.149* | |
H11E | 0.0799 | 0.1576 | 0.2263 | 0.149* | |
H11F | 0.0210 | 0.1149 | 0.1529 | 0.149* | |
C12B | 0.12071 (14) | 0.44568 (10) | 0.31785 (8) | 0.0587 (4) | |
C13B | 0.08005 (15) | 0.40606 (11) | 0.37647 (9) | 0.0683 (5) | |
H13B | 0.0359 | 0.3597 | 0.3676 | 0.082* | |
C14B | 0.10574 (16) | 0.43617 (12) | 0.44911 (10) | 0.0742 (5) | |
H14B | 0.0779 | 0.4093 | 0.4888 | 0.089* | |
C15B | 0.17119 (16) | 0.50456 (11) | 0.46458 (9) | 0.0713 (5) | |
C16B | 0.20706 (17) | 0.54460 (11) | 0.40370 (10) | 0.0775 (5) | |
H16B | 0.2488 | 0.5921 | 0.4120 | 0.093* | |
C17B | 0.18243 (16) | 0.51569 (11) | 0.33139 (10) | 0.0740 (5) | |
H17B | 0.2076 | 0.5436 | 0.2914 | 0.089* | |
C18B | 0.20426 (19) | 0.53287 (14) | 0.54477 (10) | 0.0977 (7) | |
H18D | 0.1557 | 0.5771 | 0.5550 | 0.147* | |
H18E | 0.2835 | 0.5499 | 0.5514 | 0.147* | |
H18F | 0.1946 | 0.4896 | 0.5790 | 0.147* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1A | 0.0950 (8) | 0.0923 (8) | 0.0886 (8) | −0.0115 (6) | 0.0143 (6) | −0.0005 (6) |
F2A | 0.1169 (10) | 0.1293 (10) | 0.0709 (7) | 0.0263 (8) | 0.0031 (6) | −0.0205 (7) |
F3A | 0.1122 (10) | 0.1948 (15) | 0.0880 (8) | 0.0334 (9) | 0.0454 (7) | 0.0444 (9) |
F4A | 0.1151 (11) | 0.1317 (11) | 0.1870 (16) | −0.0175 (9) | 0.0438 (10) | 0.0514 (11) |
F5A | 0.1069 (10) | 0.0924 (9) | 0.1375 (11) | −0.0086 (7) | −0.0047 (8) | −0.0170 (8) |
O10A | 0.0823 (8) | 0.0743 (8) | 0.0665 (7) | 0.0193 (7) | 0.0126 (6) | 0.0027 (6) |
N1A | 0.0828 (10) | 0.0756 (10) | 0.0563 (9) | 0.0258 (8) | 0.0089 (7) | 0.0020 (7) |
N2A | 0.0987 (12) | 0.0899 (11) | 0.0646 (10) | 0.0375 (9) | 0.0065 (8) | −0.0012 (8) |
N3A | 0.0618 (9) | 0.0734 (10) | 0.0634 (9) | 0.0017 (8) | 0.0038 (7) | −0.0055 (7) |
N4A | 0.0685 (9) | 0.0728 (10) | 0.0569 (9) | 0.0020 (8) | 0.0133 (7) | −0.0051 (8) |
C1A | 0.0639 (11) | 0.0766 (12) | 0.0601 (11) | 0.0077 (9) | 0.0107 (8) | 0.0083 (9) |
C2A | 0.0716 (12) | 0.0924 (14) | 0.0605 (12) | 0.0183 (11) | 0.0034 (9) | 0.0010 (11) |
C3A | 0.0735 (13) | 0.1160 (18) | 0.0711 (14) | 0.0230 (13) | 0.0220 (11) | 0.0245 (13) |
C4A | 0.0692 (13) | 0.0902 (15) | 0.1136 (19) | 0.0026 (12) | 0.0197 (13) | 0.0332 (14) |
C5A | 0.0687 (12) | 0.0763 (13) | 0.0839 (14) | 0.0047 (10) | 0.0017 (10) | 0.0039 (11) |
C6A | 0.0642 (11) | 0.0728 (12) | 0.0556 (10) | 0.0148 (9) | 0.0056 (8) | 0.0058 (9) |
C7A | 0.0625 (10) | 0.0691 (11) | 0.0540 (10) | 0.0085 (9) | 0.0029 (8) | 0.0003 (9) |
C8A | 0.0630 (10) | 0.0778 (12) | 0.0529 (10) | 0.0055 (9) | 0.0043 (8) | −0.0026 (9) |
C9A | 0.0807 (13) | 0.0910 (14) | 0.0615 (11) | 0.0263 (11) | 0.0035 (9) | −0.0060 (10) |
C11A | 0.130 (2) | 0.133 (2) | 0.0817 (14) | 0.0615 (16) | 0.0169 (13) | −0.0128 (13) |
C12A | 0.0658 (11) | 0.0677 (11) | 0.0486 (9) | −0.0101 (9) | 0.0058 (8) | −0.0010 (8) |
C13A | 0.0646 (10) | 0.0672 (11) | 0.0649 (11) | −0.0094 (8) | 0.0078 (8) | −0.0053 (9) |
C14A | 0.0803 (13) | 0.0889 (14) | 0.0588 (11) | −0.0198 (11) | 0.0179 (9) | −0.0071 (9) |
C15A | 0.0766 (12) | 0.0909 (14) | 0.0633 (11) | −0.0113 (11) | 0.0056 (9) | 0.0105 (10) |
C16A | 0.0830 (13) | 0.0980 (15) | 0.0780 (13) | 0.0120 (11) | 0.0106 (11) | 0.0181 (11) |
C17A | 0.0844 (13) | 0.0882 (14) | 0.0645 (11) | 0.0094 (11) | 0.0174 (9) | 0.0043 (10) |
C18A | 0.1191 (19) | 0.162 (2) | 0.0724 (14) | −0.0046 (17) | 0.0057 (12) | 0.0375 (14) |
F1B | 0.0835 (8) | 0.0933 (8) | 0.1162 (9) | 0.0196 (6) | 0.0115 (6) | −0.0046 (7) |
F2B | 0.1358 (11) | 0.1061 (9) | 0.0878 (8) | −0.0048 (8) | −0.0235 (7) | 0.0239 (7) |
F3B | 0.1462 (11) | 0.1374 (11) | 0.0686 (7) | −0.0499 (9) | 0.0320 (7) | −0.0197 (7) |
F4B | 0.0968 (9) | 0.1225 (10) | 0.1423 (11) | 0.0043 (8) | 0.0426 (8) | −0.0431 (9) |
F5B | 0.0954 (8) | 0.0803 (8) | 0.1086 (9) | 0.0133 (6) | −0.0129 (7) | 0.0021 (7) |
O10B | 0.0943 (9) | 0.0585 (7) | 0.0640 (7) | −0.0063 (6) | 0.0136 (6) | −0.0061 (6) |
N1B | 0.0915 (11) | 0.0600 (9) | 0.0595 (9) | −0.0147 (8) | 0.0117 (8) | −0.0068 (7) |
N2B | 0.1015 (12) | 0.0608 (9) | 0.0697 (10) | −0.0201 (8) | 0.0098 (8) | −0.0058 (7) |
N3B | 0.0604 (8) | 0.0651 (9) | 0.0612 (9) | −0.0028 (7) | 0.0080 (6) | −0.0027 (7) |
N4B | 0.0776 (10) | 0.0624 (10) | 0.0544 (9) | −0.0025 (7) | 0.0142 (7) | −0.0013 (7) |
C1B | 0.0667 (12) | 0.0605 (11) | 0.0707 (12) | −0.0012 (9) | 0.0011 (9) | −0.0109 (9) |
C2B | 0.0876 (14) | 0.0690 (12) | 0.0605 (11) | −0.0129 (10) | −0.0093 (10) | 0.0025 (9) |
C3B | 0.0971 (15) | 0.0845 (14) | 0.0537 (11) | −0.0281 (12) | 0.0147 (11) | −0.0173 (10) |
C4B | 0.0729 (13) | 0.0727 (12) | 0.0871 (14) | −0.0069 (10) | 0.0160 (11) | −0.0254 (11) |
C5B | 0.0729 (12) | 0.0586 (11) | 0.0663 (11) | −0.0042 (9) | −0.0020 (9) | −0.0115 (9) |
C6B | 0.0683 (11) | 0.0575 (10) | 0.0553 (10) | −0.0079 (9) | 0.0046 (8) | −0.0114 (8) |
C7B | 0.0629 (10) | 0.0589 (11) | 0.0582 (10) | −0.0043 (8) | 0.0040 (8) | −0.0064 (8) |
C8B | 0.0627 (10) | 0.0635 (11) | 0.0566 (10) | −0.0056 (8) | 0.0063 (8) | −0.0041 (8) |
C9B | 0.0792 (12) | 0.0669 (12) | 0.0641 (11) | −0.0154 (9) | 0.0064 (9) | −0.0027 (9) |
C11B | 0.1329 (19) | 0.0775 (14) | 0.0895 (14) | −0.0324 (13) | 0.0180 (13) | 0.0025 (11) |
C12B | 0.0633 (10) | 0.0630 (10) | 0.0503 (9) | 0.0068 (8) | 0.0092 (7) | −0.0012 (8) |
C13B | 0.0705 (11) | 0.0732 (12) | 0.0625 (11) | −0.0021 (9) | 0.0139 (8) | 0.0002 (9) |
C14B | 0.0845 (13) | 0.0840 (13) | 0.0557 (11) | 0.0059 (11) | 0.0154 (9) | 0.0068 (9) |
C15B | 0.0791 (12) | 0.0753 (12) | 0.0590 (11) | 0.0165 (10) | 0.0071 (9) | −0.0087 (9) |
C16B | 0.0955 (14) | 0.0694 (12) | 0.0688 (12) | −0.0054 (10) | 0.0151 (10) | −0.0133 (10) |
C17B | 0.0979 (14) | 0.0649 (11) | 0.0620 (11) | −0.0057 (10) | 0.0213 (9) | −0.0021 (9) |
C18B | 0.1170 (17) | 0.1100 (17) | 0.0640 (12) | 0.0154 (14) | 0.0040 (11) | −0.0182 (11) |
F1A—C1A | 1.330 (2) | F1B—C1B | 1.3302 (19) |
F2A—C2A | 1.334 (2) | F2B—C2B | 1.330 (2) |
F3A—C3A | 1.340 (2) | F3B—C3B | 1.332 (2) |
F4A—C4A | 1.344 (2) | F4B—C4B | 1.346 (2) |
F5A—C5A | 1.337 (2) | F5B—C5B | 1.3382 (19) |
O10A—C7A | 1.2228 (19) | O10B—C7B | 1.2265 (18) |
N1A—C7A | 1.375 (2) | N1B—C7B | 1.376 (2) |
N1A—C6A | 1.403 (2) | N1B—C6B | 1.404 (2) |
N1A—N2A | 1.4134 (19) | N1B—N2B | 1.4133 (18) |
N2A—C9A | 1.294 (2) | N2B—C9B | 1.304 (2) |
N3A—N4A | 1.2945 (19) | N3B—N4B | 1.3024 (18) |
N3A—C8A | 1.326 (2) | N3B—C8B | 1.3235 (19) |
N4A—C12A | 1.417 (2) | N4B—C12B | 1.409 (2) |
N4A—H4A | 0.863 (9) | N4B—H4B | 0.858 (9) |
C1A—C2A | 1.365 (2) | C1B—C2B | 1.373 (2) |
C1A—C6A | 1.380 (2) | C1B—C6B | 1.377 (2) |
C2A—C3A | 1.358 (3) | C2B—C3B | 1.371 (3) |
C3A—C4A | 1.356 (3) | C3B—C4B | 1.366 (3) |
C4A—C5A | 1.370 (3) | C4B—C5B | 1.360 (3) |
C5A—C6A | 1.378 (3) | C5B—C6B | 1.376 (2) |
C7A—C8A | 1.447 (2) | C7B—C8B | 1.450 (2) |
C8A—C9A | 1.426 (2) | C8B—C9B | 1.429 (2) |
C9A—C11A | 1.496 (3) | C9B—C11B | 1.488 (2) |
C11A—H11A | 0.9600 | C11B—H11D | 0.9600 |
C11A—H11B | 0.9600 | C11B—H11E | 0.9600 |
C11A—H11C | 0.9600 | C11B—H11F | 0.9600 |
C12A—C17A | 1.366 (2) | C12B—C13B | 1.371 (2) |
C12A—C13A | 1.380 (2) | C12B—C17B | 1.374 (2) |
C13A—C14A | 1.387 (2) | C13B—C14B | 1.386 (2) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.380 (3) | C14B—C15B | 1.378 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.381 (3) | C15B—C16B | 1.384 (2) |
C15A—C18A | 1.515 (2) | C15B—C18B | 1.508 (2) |
C16A—C17A | 1.370 (2) | C16B—C17B | 1.372 (2) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—H18A | 0.9600 | C18B—H18D | 0.9600 |
C18A—H18B | 0.9600 | C18B—H18E | 0.9600 |
C18A—H18C | 0.9600 | C18B—H18F | 0.9600 |
C7A—N1A—C6A | 127.08 (14) | C7B—N1B—C6B | 126.54 (14) |
C7A—N1A—N2A | 112.76 (13) | C7B—N1B—N2B | 112.76 (13) |
C6A—N1A—N2A | 119.13 (13) | C6B—N1B—N2B | 120.14 (13) |
C9A—N2A—N1A | 106.04 (14) | C9B—N2B—N1B | 106.23 (14) |
N4A—N3A—C8A | 117.04 (14) | N4B—N3B—C8B | 117.36 (14) |
N3A—N4A—C12A | 121.24 (14) | N3B—N4B—C12B | 120.55 (14) |
N3A—N4A—H4A | 119.9 (12) | N3B—N4B—H4B | 122.0 (13) |
C12A—N4A—H4A | 118.3 (12) | C12B—N4B—H4B | 116.5 (13) |
F1A—C1A—C2A | 118.48 (17) | F1B—C1B—C2B | 119.00 (17) |
F1A—C1A—C6A | 119.79 (15) | F1B—C1B—C6B | 119.40 (16) |
C2A—C1A—C6A | 121.74 (18) | C2B—C1B—C6B | 121.60 (17) |
F2A—C2A—C3A | 119.42 (18) | F2B—C2B—C3B | 119.95 (18) |
F2A—C2A—C1A | 120.97 (19) | F2B—C2B—C1B | 120.82 (19) |
C3A—C2A—C1A | 119.61 (19) | C3B—C2B—C1B | 119.23 (17) |
F3A—C3A—C4A | 120.1 (2) | F3B—C3B—C4B | 120.3 (2) |
F3A—C3A—C2A | 119.7 (2) | F3B—C3B—C2B | 119.7 (2) |
C4A—C3A—C2A | 120.17 (19) | C4B—C3B—C2B | 119.99 (18) |
F4A—C4A—C3A | 120.3 (2) | F4B—C4B—C5B | 120.5 (2) |
F4A—C4A—C5A | 119.5 (2) | F4B—C4B—C3B | 119.3 (2) |
C3A—C4A—C5A | 120.3 (2) | C5B—C4B—C3B | 120.11 (18) |
F5A—C5A—C4A | 119.7 (2) | F5B—C5B—C4B | 118.64 (18) |
F5A—C5A—C6A | 119.32 (18) | F5B—C5B—C6B | 119.81 (16) |
C4A—C5A—C6A | 121.0 (2) | C4B—C5B—C6B | 121.50 (18) |
C5A—C6A—C1A | 117.24 (17) | C5B—C6B—C1B | 117.56 (16) |
C5A—C6A—N1A | 121.47 (17) | C5B—C6B—N1B | 120.68 (16) |
C1A—C6A—N1A | 121.28 (16) | C1B—C6B—N1B | 121.72 (16) |
O10A—C7A—N1A | 126.35 (15) | O10B—C7B—N1B | 126.48 (15) |
O10A—C7A—C8A | 130.57 (15) | O10B—C7B—C8B | 130.38 (15) |
N1A—C7A—C8A | 103.09 (14) | N1B—C7B—C8B | 103.13 (14) |
N3A—C8A—C9A | 125.20 (16) | N3B—C8B—C9B | 125.40 (16) |
N3A—C8A—C7A | 128.25 (16) | N3B—C8B—C7B | 127.56 (15) |
C9A—C8A—C7A | 106.51 (15) | C9B—C8B—C7B | 106.72 (14) |
N2A—C9A—C8A | 111.59 (16) | N2B—C9B—C8B | 111.13 (15) |
N2A—C9A—C11A | 122.00 (18) | N2B—C9B—C11B | 121.15 (16) |
C8A—C9A—C11A | 126.40 (17) | C8B—C9B—C11B | 127.72 (16) |
C9A—C11A—H11A | 109.5 | C9B—C11B—H11D | 109.5 |
C9A—C11A—H11B | 109.5 | C9B—C11B—H11E | 109.5 |
H11A—C11A—H11B | 109.5 | H11D—C11B—H11E | 109.5 |
C9A—C11A—H11C | 109.5 | C9B—C11B—H11F | 109.5 |
H11A—C11A—H11C | 109.5 | H11D—C11B—H11F | 109.5 |
H11B—C11A—H11C | 109.5 | H11E—C11B—H11F | 109.5 |
C17A—C12A—C13A | 120.47 (16) | C13B—C12B—C17B | 119.86 (15) |
C17A—C12A—N4A | 117.83 (15) | C13B—C12B—N4B | 121.62 (16) |
C13A—C12A—N4A | 121.69 (16) | C17B—C12B—N4B | 118.50 (15) |
C12A—C13A—C14A | 118.98 (17) | C12B—C13B—C14B | 119.02 (17) |
C12A—C13A—H13A | 120.5 | C12B—C13B—H13B | 120.5 |
C14A—C13A—H13A | 120.5 | C14B—C13B—H13B | 120.5 |
C15A—C14A—C13A | 121.60 (16) | C15B—C14B—C13B | 122.24 (17) |
C15A—C14A—H14A | 119.2 | C15B—C14B—H14B | 118.9 |
C13A—C14A—H14A | 119.2 | C13B—C14B—H14B | 118.9 |
C14A—C15A—C16A | 117.23 (17) | C14B—C15B—C16B | 117.11 (16) |
C14A—C15A—C18A | 121.54 (19) | C14B—C15B—C18B | 121.03 (18) |
C16A—C15A—C18A | 121.2 (2) | C16B—C15B—C18B | 121.85 (19) |
C17A—C16A—C15A | 122.28 (19) | C17B—C16B—C15B | 121.41 (18) |
C17A—C16A—H16A | 118.9 | C17B—C16B—H16B | 119.3 |
C15A—C16A—H16A | 118.9 | C15B—C16B—H16B | 119.3 |
C12A—C17A—C16A | 119.44 (17) | C16B—C17B—C12B | 120.27 (17) |
C12A—C17A—H17A | 120.3 | C16B—C17B—H17B | 119.9 |
C16A—C17A—H17A | 120.3 | C12B—C17B—H17B | 119.9 |
C15A—C18A—H18A | 109.5 | C15B—C18B—H18D | 109.5 |
C15A—C18A—H18B | 109.5 | C15B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C15A—C18A—H18C | 109.5 | C15B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C7A—N1A—N2A—C9A | 1.0 (2) | C7B—N1B—N2B—C9B | 1.9 (2) |
C6A—N1A—N2A—C9A | 170.15 (17) | C6B—N1B—N2B—C9B | 173.91 (15) |
C8A—N3A—N4A—C12A | −178.65 (14) | C8B—N3B—N4B—C12B | −173.28 (14) |
F1A—C1A—C2A—F2A | 0.3 (2) | F1B—C1B—C2B—F2B | 0.6 (2) |
C6A—C1A—C2A—F2A | −179.51 (15) | C6B—C1B—C2B—F2B | −179.86 (15) |
F1A—C1A—C2A—C3A | −179.63 (16) | F1B—C1B—C2B—C3B | −178.45 (15) |
C6A—C1A—C2A—C3A | 0.6 (3) | C6B—C1B—C2B—C3B | 1.1 (3) |
F2A—C2A—C3A—F3A | 0.7 (3) | F2B—C2B—C3B—F3B | 1.1 (3) |
C1A—C2A—C3A—F3A | −179.38 (16) | C1B—C2B—C3B—F3B | −179.91 (15) |
F2A—C2A—C3A—C4A | 178.92 (17) | F2B—C2B—C3B—C4B | 179.96 (16) |
C1A—C2A—C3A—C4A | −1.1 (3) | C1B—C2B—C3B—C4B | −1.0 (3) |
F3A—C3A—C4A—F4A | 0.0 (3) | F3B—C3B—C4B—F4B | 1.6 (3) |
C2A—C3A—C4A—F4A | −178.21 (17) | C2B—C3B—C4B—F4B | −177.32 (16) |
F3A—C3A—C4A—C5A | 179.42 (17) | F3B—C3B—C4B—C5B | 179.22 (15) |
C2A—C3A—C4A—C5A | 1.2 (3) | C2B—C3B—C4B—C5B | 0.3 (3) |
F4A—C4A—C5A—F5A | 0.0 (3) | F4B—C4B—C5B—F5B | 0.3 (3) |
C3A—C4A—C5A—F5A | −179.42 (17) | C3B—C4B—C5B—F5B | −177.35 (15) |
F4A—C4A—C5A—C6A | 178.77 (17) | F4B—C4B—C5B—C6B | 177.91 (15) |
C3A—C4A—C5A—C6A | −0.6 (3) | C3B—C4B—C5B—C6B | 0.3 (3) |
F5A—C5A—C6A—C1A | 178.83 (15) | F5B—C5B—C6B—C1B | 177.42 (14) |
C4A—C5A—C6A—C1A | 0.1 (3) | C4B—C5B—C6B—C1B | −0.2 (2) |
F5A—C5A—C6A—N1A | −0.4 (3) | F5B—C5B—C6B—N1B | −0.2 (2) |
C4A—C5A—C6A—N1A | −179.20 (16) | C4B—C5B—C6B—N1B | −177.83 (15) |
F1A—C1A—C6A—C5A | −179.83 (15) | F1B—C1B—C6B—C5B | 179.05 (14) |
C2A—C1A—C6A—C5A | 0.0 (3) | C2B—C1B—C6B—C5B | −0.5 (2) |
F1A—C1A—C6A—N1A | −0.6 (2) | F1B—C1B—C6B—N1B | −3.3 (2) |
C2A—C1A—C6A—N1A | 179.25 (15) | C2B—C1B—C6B—N1B | 177.09 (15) |
C7A—N1A—C6A—C5A | 108.5 (2) | C7B—N1B—C6B—C5B | 110.3 (2) |
N2A—N1A—C6A—C5A | −58.9 (2) | N2B—N1B—C6B—C5B | −60.4 (2) |
C7A—N1A—C6A—C1A | −70.7 (2) | C7B—N1B—C6B—C1B | −67.2 (2) |
N2A—N1A—C6A—C1A | 121.86 (18) | N2B—N1B—C6B—C1B | 122.02 (18) |
C6A—N1A—C7A—O10A | 11.6 (3) | C6B—N1B—C7B—O10B | 7.4 (3) |
N2A—N1A—C7A—O10A | 179.68 (17) | N2B—N1B—C7B—O10B | 178.75 (16) |
C6A—N1A—C7A—C8A | −168.41 (16) | C6B—N1B—C7B—C8B | −172.48 (15) |
N2A—N1A—C7A—C8A | −0.28 (19) | N2B—N1B—C7B—C8B | −1.11 (18) |
N4A—N3A—C8A—C9A | 175.80 (16) | N4B—N3B—C8B—C9B | 174.23 (16) |
N4A—N3A—C8A—C7A | −1.5 (3) | N4B—N3B—C8B—C7B | 1.6 (2) |
O10A—C7A—C8A—N3A | −2.8 (3) | O10B—C7B—C8B—N3B | −6.1 (3) |
N1A—C7A—C8A—N3A | 177.21 (16) | N1B—C7B—C8B—N3B | 173.72 (16) |
O10A—C7A—C8A—C9A | 179.58 (18) | O10B—C7B—C8B—C9B | −179.89 (18) |
N1A—C7A—C8A—C9A | −0.45 (19) | N1B—C7B—C8B—C9B | −0.04 (18) |
N1A—N2A—C9A—C8A | −1.3 (2) | N1B—N2B—C9B—C8B | −1.9 (2) |
N1A—N2A—C9A—C11A | 179.31 (19) | N1B—N2B—C9B—C11B | 178.53 (17) |
N3A—C8A—C9A—N2A | −176.63 (17) | N3B—C8B—C9B—N2B | −172.68 (16) |
C7A—C8A—C9A—N2A | 1.1 (2) | C7B—C8B—C9B—N2B | 1.3 (2) |
N3A—C8A—C9A—C11A | 2.8 (3) | N3B—C8B—C9B—C11B | 6.9 (3) |
C7A—C8A—C9A—C11A | −179.5 (2) | C7B—C8B—C9B—C11B | −179.19 (19) |
N3A—N4A—C12A—C17A | 166.96 (16) | N3B—N4B—C12B—C13B | −18.4 (2) |
N3A—N4A—C12A—C13A | −13.2 (2) | N3B—N4B—C12B—C17B | 160.29 (15) |
C17A—C12A—C13A—C14A | −0.3 (2) | C17B—C12B—C13B—C14B | −2.3 (3) |
N4A—C12A—C13A—C14A | 179.78 (14) | N4B—C12B—C13B—C14B | 176.44 (15) |
C12A—C13A—C14A—C15A | −0.1 (3) | C12B—C13B—C14B—C15B | −0.2 (3) |
C13A—C14A—C15A—C16A | 0.7 (3) | C13B—C14B—C15B—C16B | 2.6 (3) |
C13A—C14A—C15A—C18A | −179.54 (17) | C13B—C14B—C15B—C18B | −175.97 (16) |
C14A—C15A—C16A—C17A | −0.9 (3) | C14B—C15B—C16B—C17B | −2.5 (3) |
C18A—C15A—C16A—C17A | 179.30 (19) | C18B—C15B—C16B—C17B | 176.00 (17) |
C13A—C12A—C17A—C16A | 0.1 (3) | C15B—C16B—C17B—C12B | 0.2 (3) |
N4A—C12A—C17A—C16A | −179.99 (17) | C13B—C12B—C17B—C16B | 2.3 (3) |
C15A—C16A—C17A—C12A | 0.5 (3) | N4B—C12B—C17B—C16B | −176.44 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4a—H4a···O10a | 0.86 (2) | 2.16 (1) | 2.833 (2) | 134 (2) |
N4a—H4a···O10b | 0.86 (2) | 2.49 (2) | 3.044 (2) | 122 (1) |
N4b—H4b···O10a | 0.86 (2) | 2.56 (2) | 3.036 (2) | 116 (1) |
N4b—H4b···O10b | 0.86 (2) | 2.17 (1) | 2.818 (2) | 133 (1) |
C11a—H11b···F3ai | 0.96 | 2.55 | 3.264 (3) | 132 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H11F5N4O |
Mr | 382.30 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 11.6678 (12), 16.6283 (17), 17.8362 (18) |
β (°) | 97.368 (2) |
V (Å3) | 3431.9 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.32 × 0.22 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS in SAINT-NT; Bruker, 2002) |
Tmin, Tmax | 0.96, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28507, 7711, 4062 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.123, 0.92 |
No. of reflections | 7711 |
No. of parameters | 495 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.12 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Bond | (Ia) | (Ib) | (II) | (III) |
N1—C7 | 1.374 (2) | 1.377 (2) | 1.344 (4) | 1.354 (2) |
C7—C8 | 1.447 (2) | 1.447 (2) | 1.377 (4) | 1.384 (2) |
C8—C9 | 1.426 (2) | 1.428 (2) | 1.417 (4) | 1.428 (2) |
C9—N2 | 1.294 (2) | 1.305 (2) | 1.310 (3) | 1.326 (2) |
C8—N3 | 1.328 (2) | 1.326 (2) | 1.388 (4) | 1.393 (2) |
N3—N4 | 1.293 (2) | 1.303 (2) | 1.258 (3) | 1.249 (2) |
N4—C12 | 1.422 (2) | 1.411 (2) | 1.423 (4) | 1.426 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4a—H4a···O10a | 0.864 (16) | 2.164 (14) | 2.833 (2) | 134.0 (15) |
N4a—H4a···O10b | 0.864 (16) | 2.493 (17) | 3.044 (2) | 122.3 (14) |
N4b—H4b···O10a | 0.855 (15) | 2.561 (18) | 3.036 (2) | 116.1 (13) |
N4b—H4b···O10b | 0.855 (15) | 2.168 (14) | 2.818 (2) | 132.7 (13) |
C11a—H11b···F3ai | 0.96 | 2.55 | 3.264 (3) | 132 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Group 1···Group 2 | CCD (Å) | DA (°) | IPD (Å) |
Cg2a···Cg3b | 3.6853 (13) | 10.68 (10) | 3.50 (6) |
Cg2b···Cg3a | 3.6982 (12) | 9.67 (10) | 3.47 (1) |
Ring-centroid codes (see also Fig. 1): Cg2a is the centroid of the ring C1a–C6a, Cg3a that of C12a–C17a, Cg2b that of C1b–C6b and Cg3b that of C12b–C17b. CCD is the centre-to-centre distance, DA is the dihedral angle between rings and IPD is the interplanar distance, or the (mean) distance from one plane to the neighbouring centroid. For details, see Janiak (2000). |