Download citation
Download citation
link to html
Crystals of the title compounds, 20-(4-pyrid­yl)porphyrin-54,104,154-tribenzoic acid–dimethyl sulfoxide (2/5), C46H29N5O6·2.5C2H6OS, (I), and 20-(4-pyrid­yl)porphyrin-54,104,154-tribenzoic acid–4-acetyl­pyridine–tetra­hydro­furan (1/2/10), C46H29N5O6·2C7H7NO·10C4H8O, (II), consist of hydrogen-bonded supra­molecular chains of porphyrin units solvated by mol­ecules of dimethyl sulfoxide [in (I)] and 4-acetyl­pyridine [in (II)]. In (I), these chains consist of heterogeneous arrays with alternating porphyrin and dimethyl sulfoxide species, being sustained by COOH...O=S hydrogen bonds. They adopt a zigzag geometry and link on both sides to additional mol­ecules of dimethyl sulfoxide. In (II), the chains consist of homogeneous linear supra­molecular arrays of porphyrin units, which are directly connected to one another via COOH...N(pyridyl) hydrogen bonds. As in the previous case, these arrays are solvated on both sides by mol­ecules of the 4-­acetyl­pyridine ligand via similar COOH(porphyrin)...N(ligand) hydrogen bonds. The two crystal structures contain wide inter­porphyrin voids, which accommodate disordered/diffused solvent mol­ecules, viz. dimethyl sulfoxide in (I) and tetra­hydro­furan in (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107024936/ln3055sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107024936/ln3055Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107024936/ln3055IIsup3.hkl
Contains datablock II

CCDC references: 655507; 655508

Comment top

Following our earlier studies on the designed construction of framework solids from symmetrically functionalized porphyrin building blocks of square-planar D4h symmetry (Goldberg, 2005, and references therein), the supramolecular chemistry of porphyrin derivatives of reduced symmetry has also deserved considerable attention (Vinodu & Goldberg, 2003; George & Goldberg, 2006; George et al., 2006). Within this context, porphyrin cores substituted with either four, three or two carboxylic acid functions of complementary hydrogen-bonding capacity have been investigated (Diskin-Posner & Goldberg, 1999; Vinodu & Goldberg, 2003, 2004). In most cases, the predominant propensity of such porphyrin species to associate directly via the cyclic dimeric (COOH)2 hydrogen-bonding synthon into polymeric arrays has been demonstrated. However, disruption of this binding mode may occur in the presence of strong pyridyl- and sulfoxide-type Lewis base reagents, owing to competing solvation (Lipstman et al., 2006; George et al., 2006). Thus, lipophilic species, such as dimethyl sulfoxide (DMSO) or 4-acetylpyridine, reveal preferential affinity to associate to the carboxylic acid functions via hydrogen bonds, in competition with the alternative (COOH)2 self-association of the porphyrin units. Furthermore, in porphyrins that bear both the 3-pyridyl as well as the 4-carboxyphenyl functions, intermolecular COOH···pyridyl hydrogen bonding has been observed (Vinodu & Goldberg, 2005).

Within the above context, we report here on the synthesis of the title porphyrin compound, and the structures of its 1:2 adducts with dimethyl sulfoxide, (I), and 4-acetylpyridine, (II), that crystallized as dimethyl sulfoxide and tetrahydrofuran solvates, respectively.

As shown previously, the present study also reveals preferential formation of COOH···OS and COOH···Npyridine hydrogen bonds, rather than the (COOH)2 interactions. Figs. 1 and 2 depict the molecular structures of adducts (I) and (II), respectively. The DMSO species is a strong acceptor of H atoms in hydrogen bonds, which can associate with either one or two COOH H-atom donors. In (I), they solvate completely the three carboxylic acid groups by relatively strong OH···OS hydrogen bonds with O···O distances ranging from 2.565 (6) to 2.624 (5) Å (Table 1). While one molecule of DMSO connects to a single COOH group, the other ligand bridges between two neighboring units, thus giving rise to the formation of heterogeneous porphyrin–DMSO hydrogen-bonded zigzag polymeric arrays (Fig. 3). The crystal packing of these chains is associated with occlusion of additional uncoordinated molecules of DMSO between these chains in a disordered manner. It is of further interest to note that in the presence of very strong hydrogen bond acceptors, such as DMSO in excess, the porphyrin's pyridyl function (a somewhat weaker acceptor) is not involved in interporphyrin hydrogen bonds with the carboxylic acid groups, as observed earlier (Vinodu & Goldberg, 2004, 2003). Rather, it is involved in a weak C—H···N contact with a neighboring porphyrin unit (Table 1).

When the DMSO is replaced by a 4-acetylpyridine reagent in the crystallization mixture, a different intermolecular binding pattern emerges. Now the 4-acetylpyridine and the porphyrin-bound pyridyl groups have similar affinity, as hydrogen-bond acceptors, for the formation of COOH···N hydrogen bonds. This is well expressed in the observed structure of (II), crystallized from a 1:1 mixture of 4-acetylpyridine and tetrahydrofuran (THF, which is a very weak H-atom acceptor in hydrogen bonds). Thus, in order to optimally satisfy the hydorgen-bonding capacity of the porphyrin and the 4-acetylpyridine groups, one unit of the former associates with two units of the latter, wherein two of the carboxylic acid functions are solvated by two molecules of 4-acetylpyridine via COOH···N hydrogen bonds. In addition, the porphyrin scaffolds self-associate into homogeneous linear polymeric chains via COOH···N(pyridyl) hydrogen bonds (Fig. 4). The corresponding O···N distances range from 2.596 (5) to 2.653 (4) Å (Table 2). In this arrangement, the hydorgen-bonding potential of all COOH and N(pyridine/pyridyl) sites is used optimally. Side packing of these chains creates open layers, which in turn stack one on top of the other, yielding a stable structure at room temperature. This stability may be attributed to attractive dispersion between the large aromatic surfaces of adjacent layers, as well as to additional weak C—H···O interactions between the molecular entities (Table 2). The crystal packing of the supramolecular arrays creates very wide interporphyrin voids, which propagate parallel to the a axis, accommodating severely diffuse THF solvent molecules (Fig. 5). The van der Waals width of these canals is about 9–10 Å.

This study, along with our earlier observations, confirms the hierarchy of the hydrogen-bonding interactions expressed in the supramolecular assembly of the carboxyphenylporphyrin materials: the COOH···OS synthon appears more stable than the COOH···N(pyridine) one, while the (COOH)2 interaction seems to be the least preferred among the three types (Lipstman et al., 2006; George et al., 2006; Etter, 1990, 1991). Owing to severe solubility problems, we have not been able so far to crystallize two-dimensionally hydrogen-bonded supramolecular arrays of the title porphyrin compound in the absence of the competing solvents, as was achieved successfully with the tetracarboxyphenyl (Diskin-Posner & Goldberg, 1999) and 3-pyridyltris(4-carboxyphenyl) (Vinodu & Goldberg, 2005) derivatives. Only one single-crystal structure of a compound containing 4-pyridyl and 4-carboxyphenyl functional substituents on the same porphyrin framework has ever been published before (Redman et al., 2001).

Related literature top

For related literature, see: Adler et al. (1970); Diskin-Posner & Goldberg (1999); Etter (1990, 1991); George & Goldberg (2006); George, Lipstman, Muniappan & Goldberg (2006); Gianferrara et al. (2007); Goldberg (2005); Lipstman et al. (2006); Redman et al. (2001); Sheldrick (1997); Spek (2003); Vinodu & Goldberg (2003, 2004, 2005).

Experimental top

The free-base porphyrin species was synthesized by a two-step procedure. The first step is the synthesis of 5-(4-pyridyl)-10,15,20-tris(4-carbomethoxyphenyl)porphyrin by Adler's method (Adler et al., 1970). This involves the condensation of a 3:1 mixture of 4-pyridinecarboxaldehyde and 4-carbomethoxybenzaldehyde with distilled pyrrole in hot propionic acid, and separation of the product on a silica-gel column using chloroform as solvent and acetone–chloroform mixtures of gradually varying composition as eluants. Thus isolated 5-(4-pyridyl)-10,15,20-tris(4-carbomethoxyphenyl)porphyrin was then converted to the corresponding carboxylic acid derivative 5-(4-pyridyl)-10,15,20-tris(4-carboxyphenyl)porphyrin by alkaline hydrolysis with an aqueous solution of KOH. 5-(4-Pyridyl)-10,15,20-tris(4-carbomethoxyphenyl)porphyrin: 1H NMR (CDCl3): δ 9.00 (d, J = 5.9 Hz, 2H), 8.79 (m, 8H), 8.43 (d, J = 8 Hz, 6H), 8.25 (d, J = 8.2 Hz, 6H), 8.12 (d, J = 5.9 Hz, 2H), 4.08 (s, 12H), -2.89 (s, 2H). UV–vis (in THF, nm): λmax (logε) 417 (5.71), 513 (4.41), 547 (4.03), 590 (3.92), 649 (3.73). FAB–MS (m/z) for C49H35N5O6: found 790, calculated 789.85. 5-(4-Pyridyl)-10,15,20-tris(4-carboxyphenyl)porphyrin: 1H NMR (DMSO-d): δ 13.30 (s, 3H), 9.07 (d, J = 4.8 Hz, 2H), 8.87 (d, J = 2 Hz, 6H), 8.47–8.25 (m, 16H), -2.97 (s, 2H). UV–vis (in THF, nm): λmax (logε) 417 (5.65), 513 (4.30), 546 (3.84), 589 (3.60), 646 (3.14). FAB–MS (m/z) for C46H29N5O6: found 748, calcualted 747.77. The carboxyphenylporphyrin was crystallized from a solution in dimethyl sulfoxide (by the solvothermal technique) as well as from a 4:1 mixture of THF and 4-acetylpyridine (by slow evaporation). The overall yield in both cases was within 5–10%. The content of the uncoordinated solvent in the two structure could not be reliably determined. Most recently, the synthesis and isolation of a series of meso-(4'-pyridyl)/(4'-carboxyphenyl) porphyrins has been reported (Gianferrara et al., 2007).

Refinement top

Both crystals diffracted poorly, with a relatively low (<50%) percentage of observed intensities above the threshold of 2σ(I) within the 0–27.5° θ range. The crystal packing of the DMSO–porphyrin and acetylpyridine–porphyrin supramolecular arrays is associated in both cases by the formation of interporphyrin voids accessible to noncoordinated solvent molecules, which were found to be severely disordered in these voids. The noncoordinated solvent molecules could not be modeled by discrete atoms in either compound. Correspondingly, the contribution of the solvent to the diffraction pattern was subtracted by the SQUEEZE procedure of PLATON (Spek, 2003). In (I), these voids consist of about 27% percent of the crystal volume (1480 Å3 per unit cell, equally distributed across four cavities). The residual electron density count amounted to 68 e per unit cell, corresponding to nearly two molecules of DMSO (the content of each of the four cavities per unit cell being equivalent to one-half of a molecule of DMSO). Conventional least-squares refinement of the same solvent-excluded structural model against the original data set converged only at R1 = 0.15. Refinement calculations with the modified data converged at R1 = 0.070 for 5171 reflections with intensities above 3σ(I) and R1 = 0.085 for 6211 reflections with intensities above the threshold of 2σ(I). The crystal structure of (I) represents a racemic twin in space group Cc. The choice of the noncentrosymmetric space group was based on better intensity-statistics indicators, as well as on our inability to obtain and refine an alternative structure model in space group C2/c. In (II), about 50% of the crystal volume comprises the solvent-accessible voids. The interporphyrin channels propagate parallel to the a axis of the crystal, and appear to accommodate severely diffused molecules of the THF solvent. Conventional refinement of the ordered supramolecular fragments of the structure converged only at R1 = 0.20. The SQUEEZE procedure indicated that the single solvent accessible void in the unit cell has a volume of 1051 Å3, and that the residual electron density count is 82 e per unit-cell (which corresponds as a lower limit to at least two molecules of THF). This assessment seems to be very inaccurate, as independent thermogravimetric analysis indicated that on heating of this material about 42% weight loss occurs around 387 K, representing a markedly higher amount of the volatile THF solvent (about ten molecules per unit cell). As the crystals were out of the solvent for about the same time prior to the diffraction and thermogravimetric analysis experiments, the latter provided a better estimate of the actual solvent content. An additional 16% weight loss occurs around 422 K, which corresponds to the evaporation of the two molecules of the acetylpyridine component. Refinement calculations with the modified data converged smoothly at R1 = 0.052. Some orientational disorder of the aromatic substituents (that could not be reliably resolved) is also evident from the elongated atomic displacement parameters of the corresponding atoms. Assignment of the correct space group for this structure posed an additional problem. The distribution of the diffracted intensities suggested that the structure is centrosymmetric (space group P1 with Z = 1), which would necessitate a twofold disorder of the porphyrin species associated with alternating orientations of the inter-porphyrin COOH···N hydrogen bond along the polymeric chain. Crystallographic refinement of the structural model in space group P1 was characterized, however, by better convergence and a more coherent description of the hydrogen-bonding scheme, although the overall structure remains pseudo-centrosymmetric. In the P1 model, the observed COOH(porphyrin)···N(porphyrin) hydrogen bond was found ordered and well defined, suggesting that the space group P1 represents the preferred choice for describing the supramolecular self-assembly in this structure.

All of the H atoms were placed in calculated positions and were constrained to ride on their parent atoms. For H atoms bound to C, the C—H distances are in the range of 0.95–0.98 Å, with Uiso(H) set at 1.5Ueq(C) for the methyl groups and 1.2Ueq(C) for other C-bound H atoms. For H atoms bound to O, the O—H distances were set at 0.84 Å, with Uiso(H) values of 1.5Ueq(O), and the positions of the H atoms were based on forming the `best' hydrogen bond to a neighboring hydrogen-bond acceptor, viz. the OS [in (I)] or pyridyl [in (II)] groups (Sheldrick, 1997). The two inner pyrrole H atoms bound to N could not be located in difference Fourier maps and were assumed to be disordered between the four N atom sites in the two structures [N—H = 0.88 Å and Uiso(H) = 1.2Ueq(N)]. In the refinement of (II), five bond-length restraints were applied to bonds C25—C30, C27—N28, C46—O48, C58—C63 and N69—C70.

Computing details top

For both compounds, data collection: Collect (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level at ca 110 K. H atoms have been omitted. Hydrogen bonds between the component species within the asymmetric unit are marked by dashed lines.
[Figure 2] Fig. 2. The molecular structure of (II), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level at ca 110 K. H atoms have been omitted. Hydrogen bonds between the component species within the asymmetric unit are marked by dashed lines.
[Figure 3] Fig. 3. A stick illustration (except for the S atoms, which are marked by small spheres) of the hydrogen-bonding interaction scheme in (I). The hydrogen bonds between the carboxylic acid functions and the DMSO ligands are denoted by dashed lines (H atoms have been omitted).
[Figure 4] Fig. 4. A stick illustration of the hydrogen-bonding scheme in (II) (dashed lines), showing direct connection between neighboring porphyrin entities and solvation of the thus formed chains by molecules of 4-acetylpyridine (indicated by `Apy').
[Figure 5] Fig. 5. A space-filling illustration of the intermolecular organization of (II), as viewed down the a axis of the crystal, perforated by 9 Å wide solvent-accessible channel voids.
(I) 20-(4-pyridyl)porphyrin-54,104,154-tribenzoic acid–dimethyl sulfoxide (2/5) top
Crystal data top
C46H29N5O6·2.5C2H6SOF(000) = 1972
Mr = 943.06Dx = 1.133 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 6.5978 (3) ÅCell parameters from 5425 reflections
b = 29.2458 (15) Åθ = 1.4–27.9°
c = 28.6630 (13) ŵ = 0.17 mm1
β = 90.521 (2)°T = 110 K
V = 5530.5 (5) Å3Plates, red
Z = 40.40 × 0.20 × 0.03 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
6211 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 27.9°, θmin = 2.6°
Detector resolution: 12.8 pixels mm-1h = 88
0.3 deg. ω scansk = 3837
18496 measured reflectionsl = 3737
11808 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.211 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.005
11808 reflectionsΔρmax = 0.83 e Å3
594 parametersΔρmin = 0.31 e Å3
2 restraintsAbsolute structure: Flack (1983), 5242 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.42 (12)
Crystal data top
C46H29N5O6·2.5C2H6SOV = 5530.5 (5) Å3
Mr = 943.06Z = 4
Monoclinic, CcMo Kα radiation
a = 6.5978 (3) ŵ = 0.17 mm1
b = 29.2458 (15) ÅT = 110 K
c = 28.6630 (13) Å0.40 × 0.20 × 0.03 mm
β = 90.521 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
6211 reflections with I > 2σ(I)
18496 measured reflectionsRint = 0.071
11808 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.211Δρmax = 0.83 e Å3
S = 1.06Δρmin = 0.31 e Å3
11808 reflectionsAbsolute structure: Flack (1983), 5242 Friedel pairs
594 parametersAbsolute structure parameter: 0.42 (12)
2 restraints
Special details top

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.

The crystals were characterized by relatively large mosaic spread. The structure was found to contain additional non-coordinated solvent (DMSO) within the intra-lattice voids, which exhibited significant disorder and could not be modeled by discrete atoms. Correspondingly, the contribution of the disordered solvent was subtracted from the diffraction pattern by the SQUEEZE procedure with the aid of the PLATON software. (Spek, 2003). Conventional refinement of the same solvent-excluded structural model against the original data set converged only at R1=0.15. The solvent accessible voids amount to 1480 Å3, about 27% of the crystal volume, with a residual electron-density count of 68 e/Å3 per unit-cell (corresponding to nearly two molecules of DMSO).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.9735 (8)0.75532 (18)0.53134 (18)0.0333 (13)
C21.0592 (8)0.77624 (18)0.49060 (17)0.0342 (12)
H21.17780.79460.48950.041*
C30.9370 (8)0.76457 (18)0.45372 (19)0.0377 (13)
H30.95480.77340.42210.045*
C40.7784 (7)0.73678 (16)0.47146 (17)0.0297 (12)
C50.6218 (7)0.71900 (16)0.44393 (16)0.0284 (11)
C60.4575 (8)0.69214 (18)0.46062 (18)0.0355 (12)
C70.3114 (8)0.6688 (2)0.43233 (19)0.0423 (14)
H70.29820.67090.39940.051*
C80.1979 (9)0.6437 (2)0.46015 (19)0.0436 (14)
H80.09140.62400.45030.052*
C90.2613 (7)0.65105 (17)0.50791 (18)0.0337 (13)
C100.1910 (7)0.62917 (18)0.54724 (18)0.0332 (12)
C110.2715 (7)0.63460 (17)0.59217 (17)0.0301 (12)
C120.1785 (8)0.61323 (18)0.63464 (18)0.0346 (13)
H120.05850.59530.63590.042*
C130.3009 (8)0.62484 (19)0.67034 (18)0.0367 (13)
H130.28340.61650.70210.044*
C140.4642 (8)0.65225 (17)0.65190 (17)0.0348 (13)
C150.6312 (8)0.66854 (19)0.67856 (18)0.0330 (13)
C160.7873 (8)0.69571 (19)0.66418 (16)0.0346 (12)
C170.9356 (8)0.71811 (18)0.69097 (18)0.0392 (13)
H170.94960.71610.72390.047*
C181.0561 (7)0.74306 (18)0.66265 (17)0.0334 (12)
H181.16890.76100.67240.040*
C190.9858 (7)0.73788 (17)0.61621 (17)0.0313 (12)
C201.0554 (7)0.76013 (16)0.57531 (19)0.0296 (11)
N210.8034 (6)0.73098 (14)0.51951 (13)0.0274 (10)
H210.72590.71500.53830.033*0.50
N220.4246 (6)0.68098 (13)0.50577 (13)0.0288 (9)
H220.49520.69100.52990.035*0.50
N230.4450 (6)0.65841 (14)0.60522 (13)0.0310 (10)
H230.52560.67420.58700.037*0.50
N240.8267 (6)0.70782 (14)0.61780 (13)0.0322 (10)
H240.75930.69760.59330.039*0.50
C250.6215 (8)0.72942 (19)0.39332 (17)0.0362 (13)
C260.4565 (9)0.7553 (2)0.37418 (19)0.0470 (15)
H260.34870.76600.39300.056*
C270.4626 (9)0.7642 (2)0.3257 (2)0.0447 (14)
H270.35750.78240.31240.054*
N280.6039 (8)0.74902 (17)0.29782 (14)0.0444 (12)
C290.7603 (9)0.7265 (2)0.31617 (18)0.0454 (14)
H290.86890.71770.29660.055*
C300.7693 (9)0.71522 (19)0.36370 (19)0.0447 (15)
H300.87940.69750.37540.054*
C310.0263 (7)0.59407 (19)0.53981 (18)0.0373 (13)
C320.1661 (8)0.6076 (2)0.52249 (18)0.0412 (14)
H320.19840.63880.51710.049*
C330.3075 (8)0.5724 (2)0.51358 (18)0.0391 (13)
H330.43930.58030.50270.047*
C340.2618 (7)0.52780 (18)0.52006 (17)0.0337 (12)
C350.0735 (7)0.51503 (18)0.53823 (16)0.0327 (12)
H350.04230.48370.54340.039*
C360.0683 (7)0.54888 (18)0.54863 (18)0.0362 (13)
H360.19540.54060.56200.043*
C370.4136 (9)0.4912 (2)0.5067 (2)0.0461 (16)
O380.5799 (6)0.50111 (14)0.49172 (17)0.0608 (12)
O390.3460 (6)0.44941 (12)0.51125 (13)0.0431 (9)
H390.42690.43120.49820.065*
C400.6221 (7)0.65808 (17)0.73043 (17)0.0319 (12)
C410.7675 (9)0.6304 (2)0.75036 (18)0.0437 (14)
H410.87610.61930.73200.052*
C420.7565 (10)0.6186 (2)0.7969 (2)0.0578 (17)
H420.85750.59940.81040.069*
C430.5980 (9)0.63466 (19)0.82441 (18)0.0395 (13)
C440.4605 (8)0.6637 (2)0.80424 (19)0.0437 (14)
H440.35610.67590.82310.052*
C450.4657 (7)0.67569 (18)0.75958 (17)0.0350 (13)
H450.36620.69580.74710.042*
C460.5868 (9)0.6189 (2)0.87347 (19)0.0501 (15)
O470.6918 (8)0.5904 (2)0.89125 (17)0.112 (2)
O480.4421 (7)0.63973 (14)0.89736 (13)0.0588 (11)
H480.40640.62300.91970.088*
C491.2184 (7)0.79360 (18)0.58330 (16)0.0301 (12)
C501.1776 (8)0.84015 (19)0.57746 (18)0.0364 (13)
H501.04930.84930.56540.044*
C511.3197 (9)0.8734 (2)0.58884 (19)0.0416 (15)
H511.28800.90490.58480.050*
C521.5101 (8)0.86040 (19)0.60628 (17)0.0347 (13)
C531.5528 (8)0.81516 (19)0.6125 (2)0.0417 (14)
H531.67970.80620.62550.050*
C541.4113 (8)0.78219 (18)0.60005 (18)0.0384 (13)
H541.44680.75080.60300.046*
C551.6565 (9)0.89627 (19)0.62124 (18)0.0386 (13)
O561.5896 (6)0.93832 (13)0.61762 (15)0.0572 (12)
H561.68710.95660.62030.086*
O571.8275 (5)0.88628 (13)0.63697 (14)0.0497 (10)
S582.0706 (3)0.98598 (6)0.63830 (7)0.0699 (5)
O591.8466 (7)0.99532 (16)0.6517 (2)0.0823 (15)
C602.2050 (14)1.0371 (3)0.6482 (3)0.095 (3)
H60A2.19901.04500.68130.143*
H60B2.14411.06170.62960.143*
H60C2.34661.03300.63910.143*
C612.1660 (11)0.9553 (3)0.6862 (4)0.094 (3)
H61A2.11700.92360.68470.141*
H61B2.11980.96950.71520.141*
H61C2.31450.95540.68550.141*
S620.1583 (2)0.59419 (5)0.98836 (5)0.0471 (4)
O630.3795 (5)0.60862 (12)0.98094 (11)0.0404 (9)
C640.0899 (10)0.5602 (2)0.9383 (2)0.0544 (17)
H64A0.16580.53140.93900.082*
H64B0.12240.57700.90970.082*
H64C0.05580.55360.93880.082*
C650.0242 (10)0.6456 (2)0.9742 (2)0.0582 (17)
H65A0.04270.65280.94110.087*
H65B0.07700.67080.99320.087*
H65C0.12040.64140.98040.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.030 (3)0.041 (3)0.030 (3)0.007 (3)0.001 (2)0.001 (2)
C20.038 (3)0.035 (3)0.029 (3)0.007 (2)0.002 (2)0.004 (2)
C30.034 (3)0.043 (3)0.036 (3)0.009 (3)0.009 (2)0.002 (3)
C40.026 (3)0.029 (3)0.034 (3)0.002 (2)0.007 (2)0.005 (2)
C50.028 (3)0.026 (3)0.030 (3)0.002 (2)0.005 (2)0.003 (2)
C60.031 (3)0.036 (3)0.039 (3)0.005 (2)0.005 (2)0.003 (3)
C70.038 (3)0.051 (3)0.038 (3)0.012 (3)0.009 (3)0.003 (3)
C80.038 (3)0.058 (4)0.035 (3)0.005 (3)0.001 (3)0.003 (3)
C90.029 (3)0.038 (3)0.035 (3)0.002 (2)0.012 (2)0.008 (2)
C100.025 (3)0.044 (3)0.030 (3)0.004 (2)0.005 (2)0.001 (2)
C110.025 (3)0.031 (3)0.035 (3)0.002 (2)0.002 (2)0.000 (2)
C120.026 (3)0.037 (3)0.042 (3)0.007 (2)0.013 (2)0.004 (3)
C130.034 (3)0.051 (4)0.024 (3)0.004 (3)0.004 (2)0.004 (2)
C140.043 (3)0.035 (3)0.026 (3)0.006 (3)0.007 (2)0.003 (2)
C150.019 (3)0.047 (3)0.033 (3)0.001 (2)0.001 (2)0.007 (3)
C160.033 (3)0.044 (3)0.027 (3)0.005 (3)0.005 (2)0.007 (2)
C170.044 (4)0.047 (3)0.026 (3)0.009 (3)0.016 (3)0.008 (3)
C180.020 (3)0.050 (3)0.031 (3)0.012 (2)0.002 (2)0.005 (3)
C190.023 (3)0.030 (3)0.041 (3)0.000 (2)0.010 (2)0.007 (2)
C200.024 (3)0.023 (3)0.041 (3)0.002 (2)0.001 (2)0.001 (2)
N210.027 (2)0.032 (2)0.024 (2)0.0091 (19)0.0027 (18)0.0091 (18)
N220.024 (2)0.032 (2)0.030 (2)0.0080 (19)0.0023 (17)0.0020 (19)
N230.029 (2)0.033 (2)0.031 (2)0.0017 (19)0.0027 (19)0.0006 (19)
N240.030 (2)0.034 (2)0.032 (2)0.004 (2)0.0044 (19)0.0016 (19)
C250.035 (3)0.043 (3)0.030 (3)0.009 (3)0.005 (3)0.001 (2)
C260.047 (4)0.057 (4)0.037 (3)0.006 (3)0.005 (3)0.013 (3)
C270.038 (3)0.054 (3)0.042 (3)0.009 (3)0.011 (3)0.008 (3)
N280.052 (3)0.055 (3)0.026 (2)0.012 (2)0.008 (2)0.008 (2)
C290.048 (4)0.059 (4)0.030 (3)0.011 (3)0.002 (3)0.002 (3)
C300.046 (4)0.047 (4)0.041 (3)0.002 (3)0.010 (3)0.007 (3)
C310.027 (3)0.048 (4)0.037 (3)0.011 (3)0.004 (2)0.008 (3)
C320.025 (3)0.057 (4)0.041 (3)0.014 (3)0.005 (2)0.002 (3)
C330.027 (3)0.050 (4)0.040 (3)0.005 (3)0.008 (2)0.011 (3)
C340.029 (3)0.037 (3)0.035 (3)0.014 (2)0.004 (2)0.013 (2)
C350.031 (3)0.043 (3)0.024 (3)0.002 (3)0.008 (2)0.002 (2)
C360.022 (3)0.042 (3)0.044 (3)0.003 (3)0.007 (2)0.010 (3)
C370.032 (4)0.056 (4)0.051 (4)0.013 (3)0.011 (3)0.019 (3)
O380.034 (2)0.048 (3)0.100 (4)0.007 (2)0.015 (2)0.011 (2)
O390.043 (2)0.037 (2)0.050 (2)0.0024 (19)0.0038 (18)0.0042 (18)
C400.026 (3)0.040 (3)0.030 (3)0.003 (2)0.008 (2)0.001 (2)
C410.040 (3)0.056 (4)0.035 (3)0.008 (3)0.002 (3)0.002 (3)
C420.070 (5)0.056 (4)0.047 (4)0.001 (3)0.010 (3)0.011 (3)
C430.037 (3)0.056 (4)0.026 (3)0.009 (3)0.002 (2)0.002 (3)
C440.030 (3)0.058 (4)0.043 (3)0.005 (3)0.009 (3)0.005 (3)
C450.026 (3)0.047 (3)0.032 (3)0.006 (2)0.001 (2)0.009 (2)
C460.033 (3)0.080 (4)0.037 (3)0.001 (3)0.001 (3)0.018 (3)
O470.087 (4)0.195 (6)0.055 (3)0.076 (4)0.019 (3)0.049 (3)
O480.086 (3)0.060 (3)0.031 (2)0.017 (2)0.012 (2)0.0137 (18)
C490.024 (3)0.041 (3)0.026 (3)0.001 (2)0.002 (2)0.002 (2)
C500.032 (3)0.046 (4)0.031 (3)0.001 (3)0.014 (2)0.010 (3)
C510.047 (4)0.032 (3)0.046 (3)0.007 (3)0.009 (3)0.002 (3)
C520.033 (3)0.044 (4)0.027 (3)0.008 (3)0.010 (2)0.008 (2)
C530.025 (3)0.043 (4)0.057 (4)0.000 (3)0.003 (3)0.005 (3)
C540.045 (3)0.031 (3)0.039 (3)0.012 (3)0.000 (3)0.008 (2)
C550.053 (4)0.034 (3)0.029 (3)0.011 (3)0.002 (3)0.005 (2)
O560.050 (3)0.048 (3)0.073 (3)0.016 (2)0.026 (2)0.006 (2)
O570.029 (2)0.053 (3)0.066 (3)0.0072 (19)0.015 (2)0.004 (2)
S580.0711 (14)0.0744 (12)0.0641 (11)0.0179 (10)0.0019 (9)0.0075 (10)
O590.061 (3)0.065 (3)0.121 (4)0.019 (2)0.032 (3)0.012 (3)
C600.132 (8)0.068 (5)0.086 (6)0.026 (5)0.031 (5)0.019 (4)
C610.050 (5)0.084 (6)0.147 (8)0.002 (4)0.024 (5)0.019 (5)
S620.0445 (9)0.0525 (9)0.0442 (8)0.0136 (7)0.0031 (7)0.0087 (7)
O630.041 (2)0.047 (2)0.0339 (19)0.0071 (17)0.0003 (16)0.0061 (16)
C640.056 (4)0.062 (4)0.045 (4)0.013 (3)0.010 (3)0.007 (3)
C650.044 (4)0.066 (4)0.065 (4)0.031 (3)0.007 (3)0.010 (3)
Geometric parameters (Å, º) top
C1—C201.374 (7)C32—H320.9500
C1—N211.369 (6)C33—C341.351 (7)
C1—C21.439 (7)C33—H330.9500
C2—C31.367 (7)C34—C351.394 (7)
C2—H20.9500C34—C371.513 (7)
C3—C41.423 (7)C35—C361.392 (7)
C3—H30.9500C35—H350.9500
C4—N211.396 (6)C36—H360.9500
C4—C51.395 (7)C37—O381.210 (7)
C5—C61.425 (7)C37—O391.307 (7)
C5—C251.482 (7)O39—H390.8400
C6—N221.354 (6)C40—C411.376 (7)
C6—C71.428 (7)C40—C451.429 (7)
C7—C81.321 (8)C41—C421.381 (8)
C7—H70.9500C41—H410.9500
C8—C91.444 (7)C42—C431.396 (8)
C8—H80.9500C42—H420.9500
C9—C101.380 (7)C43—C441.367 (8)
C9—N221.390 (6)C43—C461.482 (7)
C10—C111.398 (7)C44—C451.328 (7)
C10—C311.509 (7)C44—H440.9500
C11—N231.388 (6)C45—H450.9500
C11—C121.504 (7)C46—O471.195 (7)
C12—C131.341 (7)C46—O481.328 (7)
C12—H120.9500O48—H480.8400
C13—C141.447 (8)C49—C501.398 (7)
C13—H130.9500C49—C541.397 (7)
C14—N231.355 (6)C50—C511.388 (7)
C14—C151.417 (7)C50—H500.9500
C15—C161.367 (7)C51—C521.401 (7)
C15—C401.520 (7)C51—H510.9500
C16—C171.401 (7)C52—C531.364 (7)
C16—N241.402 (6)C52—C551.487 (8)
C17—C181.355 (7)C53—C541.387 (7)
C17—H170.9500C53—H530.9500
C18—C191.414 (7)C54—H540.9500
C18—H180.9500C55—O571.246 (6)
C19—N241.370 (6)C55—O561.311 (6)
C19—C201.421 (7)O56—H560.8400
C20—C491.471 (7)S58—O591.555 (6)
N21—H210.8800S58—C611.753 (8)
N22—H220.8800S58—C601.759 (8)
N23—H230.8800C60—H60A0.9800
N24—H240.8800C60—H60B0.9800
C25—C301.363 (8)C60—H60C0.9800
C25—C261.432 (8)C61—H61A0.9800
C26—C271.416 (7)C61—H61B0.9800
C26—H260.9500C61—H61C0.9800
C27—N281.310 (7)S62—O631.536 (4)
C27—H270.9500S62—C651.790 (6)
N28—C291.329 (7)S62—C641.801 (6)
C29—C301.402 (7)C64—H64A0.9800
C29—H290.9500C64—H64B0.9800
C30—H300.9500C64—H64C0.9800
C31—C361.373 (7)C65—H65A0.9800
C31—C321.415 (7)C65—H65B0.9800
C32—C331.411 (8)C65—H65C0.9800
C20—C1—N21126.5 (5)C31—C32—H32121.6
C20—C1—C2123.2 (5)C33—C32—H32121.6
N21—C1—C2110.3 (4)C34—C33—C32122.2 (5)
C3—C2—C1106.8 (5)C34—C33—H33118.9
C3—C2—H2126.6C32—C33—H33118.9
C1—C2—H2126.6C33—C34—C35120.5 (5)
C2—C3—C4107.3 (5)C33—C34—C37120.1 (5)
C2—C3—H3126.4C35—C34—C37119.4 (5)
C4—C3—H3126.4C36—C35—C34119.0 (5)
N21—C4—C5126.4 (4)C36—C35—H35120.5
N21—C4—C3110.0 (4)C34—C35—H35120.5
C5—C4—C3123.7 (4)C31—C36—C35120.7 (5)
C4—C5—C6125.3 (4)C31—C36—H36119.6
C4—C5—C25118.1 (5)C35—C36—H36119.6
C6—C5—C25116.6 (4)O38—C37—O39124.5 (5)
N22—C6—C7108.3 (5)O38—C37—C34121.1 (6)
N22—C6—C5125.6 (4)O39—C37—C34114.3 (5)
C7—C6—C5125.8 (5)C37—O39—H39109.5
C8—C7—C6107.8 (5)C41—C40—C45118.3 (4)
C8—C7—H7126.1C41—C40—C15119.4 (5)
C6—C7—H7126.1C45—C40—C15122.3 (4)
C7—C8—C9109.2 (5)C42—C41—C40120.4 (5)
C7—C8—H8125.4C42—C41—H41119.8
C9—C8—H8125.4C40—C41—H41119.8
C10—C9—N22126.5 (4)C41—C42—C43120.5 (6)
C10—C9—C8127.5 (5)C41—C42—H42119.7
N22—C9—C8105.7 (5)C43—C42—H42119.7
C9—C10—C11124.9 (5)C44—C43—C42117.9 (5)
C9—C10—C31116.6 (4)C44—C43—C46123.7 (5)
C11—C10—C31118.3 (5)C42—C43—C46118.4 (5)
N23—C11—C10127.6 (5)C45—C44—C43123.3 (5)
N23—C11—C12109.4 (4)C45—C44—H44118.4
C10—C11—C12123.0 (5)C43—C44—H44118.4
C13—C12—C11105.4 (5)C44—C45—C40119.6 (5)
C13—C12—H12127.3C44—C45—H45120.2
C11—C12—H12127.3C40—C45—H45120.2
C12—C13—C14107.9 (5)O47—C46—O48121.1 (5)
C12—C13—H13126.1O47—C46—C43126.0 (6)
C14—C13—H13126.1O48—C46—C43112.9 (5)
N23—C14—C15123.6 (5)C46—O48—H48109.5
N23—C14—C13111.8 (4)C50—C49—C54116.6 (5)
C15—C14—C13124.6 (5)C50—C49—C20119.3 (4)
C16—C15—C14128.1 (5)C54—C49—C20123.9 (5)
C16—C15—C40116.6 (4)C51—C50—C49121.7 (5)
C14—C15—C40115.0 (5)C51—C50—H50119.1
C15—C16—C17129.1 (5)C49—C50—H50119.1
C15—C16—N24125.4 (4)C50—C51—C52119.7 (5)
C17—C16—N24105.5 (5)C50—C51—H51120.2
C18—C17—C16109.5 (5)C52—C51—H51120.2
C18—C17—H17125.2C53—C52—C51119.6 (5)
C16—C17—H17125.2C53—C52—C55120.9 (5)
C17—C18—C19108.5 (4)C51—C52—C55119.3 (5)
C17—C18—H18125.8C52—C53—C54120.2 (5)
C19—C18—H18125.8C52—C53—H53119.9
N24—C19—C18106.4 (4)C54—C53—H53119.9
N24—C19—C20125.1 (4)C53—C54—C49122.1 (5)
C18—C19—C20128.5 (5)C53—C54—H54118.9
C1—C20—C19125.7 (5)C49—C54—H54118.9
C1—C20—C49119.5 (5)O57—C55—O56123.5 (5)
C19—C20—C49114.7 (4)O57—C55—C52121.5 (5)
C1—N21—C4105.7 (4)O56—C55—C52114.9 (5)
C1—N21—H21127.2C55—O56—H56109.5
C4—N21—H21127.2O59—S58—C61103.4 (4)
C6—N22—C9109.0 (4)O59—S58—C60106.8 (4)
C6—N22—H22125.5C61—S58—C6097.6 (4)
C9—N22—H22125.5S58—C60—H60A109.5
C14—N23—C11105.6 (4)S58—C60—H60B109.5
C14—N23—H23127.2H60A—C60—H60B109.5
C11—N23—H23127.2S58—C60—H60C109.5
C19—N24—C16110.0 (4)H60A—C60—H60C109.5
C19—N24—H24125.0H60B—C60—H60C109.5
C16—N24—H24125.0S58—C61—H61A109.5
C30—C25—C26117.9 (5)S58—C61—H61B109.5
C30—C25—C5123.5 (5)H61A—C61—H61B109.5
C26—C25—C5118.6 (5)S58—C61—H61C109.5
C27—C26—C25116.4 (5)H61A—C61—H61C109.5
C27—C26—H26121.8H61B—C61—H61C109.5
C25—C26—H26121.8O63—S62—C65101.9 (3)
N28—C27—C26124.3 (5)O63—S62—C64105.8 (3)
N28—C27—H27117.9C65—S62—C6499.4 (3)
C26—C27—H27117.9S62—C64—H64A109.5
C27—N28—C29118.8 (4)S62—C64—H64B109.5
N28—C29—C30121.8 (5)H64A—C64—H64B109.5
N28—C29—H29119.1S62—C64—H64C109.5
C30—C29—H29119.1H64A—C64—H64C109.5
C25—C30—C29120.6 (5)H64B—C64—H64C109.5
C25—C30—H30119.7S62—C65—H65A109.5
C29—C30—H30119.7S62—C65—H65B109.5
C36—C31—C32120.8 (5)H65A—C65—H65B109.5
C36—C31—C10119.0 (5)S62—C65—H65C109.5
C32—C31—C10120.2 (5)H65A—C65—H65C109.5
C31—C32—C33116.7 (5)H65B—C65—H65C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O56—H56···O590.841.782.565 (6)154
O48—H48···O630.841.822.599 (5)154
O39—H39···O63i0.841.792.624 (5)169
C17—H17···N28ii0.952.553.387 (6)147
Symmetry codes: (i) x1, y+1, z1/2; (ii) x+1/2, y+3/2, z+1/2.
(II) 20-(4-pyridyl)porphyrin-54,104,154-tribenzoic acid–4-acetylpyridine–tetrahydrofuran (1/2/10) top
Crystal data top
C46H29N5O6·2C7H7NO·10C4H8OZ = 1
Mr = 1711.05F(000) = 916
Triclinic, P1Dx = 1.339 Mg m3
a = 7.6005 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.6609 (10) ÅCell parameters from 7863 reflections
c = 18.6149 (12) Åθ = 1.4–28.3°
α = 77.718 (3)°µ = 0.09 mm1
β = 89.630 (4)°T = 110 K
γ = 78.805 (4)°Prism, red
V = 2122.4 (2) Å30.40 × 0.30 × 0.25 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4725 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 28.2°, θmin = 2.2°
Detector resolution: 12.8 pixels mm-1h = 108
0.5 deg. ϕ & ω scansk = 1920
24317 measured reflectionsl = 2024
10109 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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 0.80 w = 1/[σ2(Fo2) + (0.0733P)2]
where P = (Fo2 + 2Fc2)/3
10109 reflections(Δ/σ)max = 0.019
669 parametersΔρmax = 0.25 e Å3
8 restraintsΔρmin = 0.20 e Å3
Crystal data top
C46H29N5O6·2C7H7NO·10C4H8Oγ = 78.805 (4)°
Mr = 1711.05V = 2122.4 (2) Å3
Triclinic, P1Z = 1
a = 7.6005 (3) ÅMo Kα radiation
b = 15.6609 (10) ŵ = 0.09 mm1
c = 18.6149 (12) ÅT = 110 K
α = 77.718 (3)°0.40 × 0.30 × 0.25 mm
β = 89.630 (4)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
4725 reflections with I > 2σ(I)
24317 measured reflectionsRint = 0.060
10109 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0528 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 0.80Δρmax = 0.25 e Å3
10109 reflectionsΔρmin = 0.20 e Å3
669 parameters
Special details top

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.

The results below refer to crystallographic refinement after application of the SQUEEZE procedure (Spek, 2003) to the diffraction data in order the subtract from it the contribution of the severely disordered THF solvent trapped in the lattice. Due to the apparent pseudo centrosymmetric space symmetry the crystallographic refinement was based on data set with merged Friedel opposites. Conventional refinement of the same solvent excluded structural model against the original data set converged only at R1=0.20. The solvent accessible voids amount to 1051 Å3, about 50% of the crystal volume, with a residual electron-density count of 82 e/Å3 per unit-cell (corresponding to at least 2 molecules of THF).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.3180 (6)0.0668 (3)0.6753 (3)0.0476 (12)
C20.3226 (6)0.0884 (4)0.6042 (3)0.0543 (13)
H20.24710.12230.58710.065*
C30.4493 (7)0.0534 (4)0.5660 (3)0.0620 (15)
H30.47960.05930.51740.074*
C40.5337 (5)0.0057 (3)0.6086 (2)0.0399 (11)
C50.6771 (6)0.0389 (3)0.5913 (2)0.0428 (11)
C60.7563 (5)0.0846 (3)0.6315 (3)0.0384 (11)
C70.8970 (6)0.1295 (3)0.6083 (2)0.0405 (11)
H70.95530.13030.56300.049*
C80.9358 (6)0.1711 (3)0.6604 (2)0.0467 (12)
H81.02180.20810.65890.056*
C90.8194 (5)0.1475 (3)0.7185 (3)0.0431 (12)
C100.8193 (5)0.1760 (3)0.7860 (2)0.0336 (10)
C110.7107 (6)0.1487 (3)0.8464 (2)0.0403 (11)
C120.7136 (6)0.1697 (3)0.9160 (2)0.0496 (13)
H120.79110.20340.93200.060*
C130.5833 (6)0.1326 (3)0.9577 (3)0.0472 (12)
H130.55630.13581.00710.057*
C140.4989 (6)0.0893 (3)0.9125 (2)0.0424 (12)
C150.3533 (5)0.0467 (3)0.9335 (3)0.0409 (11)
C160.2739 (6)0.0003 (3)0.8876 (2)0.0415 (11)
C170.1206 (6)0.0468 (3)0.9126 (3)0.0571 (14)
H170.06120.04890.95790.069*
C180.0865 (5)0.0844 (3)0.8582 (3)0.0436 (12)
H180.00230.11940.85740.052*
C190.2121 (5)0.0622 (3)0.7986 (2)0.0353 (10)
C200.2099 (5)0.0866 (3)0.7323 (3)0.0437 (12)
N210.4514 (4)0.0151 (2)0.67491 (18)0.0375 (9)
H210.47770.00780.71180.045*0.50
N220.7111 (4)0.0947 (2)0.70131 (19)0.0371 (9)
H220.62990.07190.72880.045*0.50
N230.5828 (4)0.0971 (2)0.8457 (2)0.0430 (10)
H230.55870.07320.80910.052*0.50
N240.3243 (4)0.0114 (2)0.81933 (18)0.0389 (9)
H240.41070.00920.79370.047*0.50
C250.7530 (6)0.0305 (3)0.5172 (2)0.0528 (13)
C260.8549 (6)0.0486 (3)0.5058 (3)0.0650 (15)
H260.87240.09970.54490.078*
C270.9309 (6)0.0555 (3)0.4402 (3)0.0776 (17)
H270.99950.11130.43490.093*
N280.9116 (6)0.0130 (4)0.3842 (2)0.0971 (19)
C290.8052 (11)0.0867 (5)0.3918 (3)0.119 (3)
H290.77980.13460.35010.143*
C300.7267 (9)0.0987 (3)0.4580 (3)0.116 (3)
H300.65530.15470.46110.139*
C310.9417 (6)0.2368 (3)0.7977 (2)0.0384 (11)
C321.1252 (5)0.2165 (3)0.7929 (2)0.0371 (11)
H321.17840.16100.78180.045*
C331.2353 (6)0.2738 (3)0.8036 (3)0.0450 (12)
H331.36220.25760.80200.054*
C341.1498 (6)0.3588 (3)0.8174 (2)0.0423 (11)
C350.9683 (6)0.3788 (3)0.8204 (3)0.0540 (14)
H350.91350.43530.82950.065*
C360.8597 (5)0.3203 (3)0.8109 (3)0.0492 (13)
H360.73300.33610.81320.059*
C371.2709 (7)0.4202 (4)0.8286 (3)0.0541 (14)
O381.4358 (4)0.3999 (2)0.8325 (2)0.0626 (10)
O391.1830 (4)0.4959 (2)0.8365 (3)0.0744 (12)
H391.25410.52550.84900.112*
C400.2706 (4)0.0544 (2)1.00409 (13)0.0490 (13)
C410.1719 (4)0.1355 (2)1.01351 (15)0.082 (2)
H410.15560.18620.97390.098*
C420.0970 (4)0.1425 (2)1.08084 (19)0.099 (2)
H420.02950.19801.08730.119*
C430.1208 (4)0.0684 (3)1.13876 (14)0.0589 (15)
C440.2195 (4)0.0128 (2)1.12933 (15)0.0695 (15)
H440.23580.06351.16890.083*
C450.2944 (4)0.01979 (18)1.06200 (18)0.0585 (13)
H450.36190.07531.05560.070*
C460.0493 (6)0.0673 (4)1.2136 (2)0.0773 (13)
O470.0269 (6)0.1360 (4)1.2294 (3)0.1349 (17)
O480.0651 (6)0.0114 (3)1.2632 (2)0.1076 (16)
H480.03030.00171.30410.178*
C490.0948 (5)0.1540 (3)0.7238 (2)0.0401 (11)
C500.0953 (5)0.1306 (3)0.7284 (2)0.0455 (12)
H500.15070.07440.73770.055*
C510.1975 (5)0.1924 (3)0.7189 (2)0.0397 (11)
H510.32400.17760.72270.048*
C520.1253 (5)0.2721 (3)0.7044 (2)0.0388 (11)
C530.0650 (5)0.2973 (3)0.7015 (2)0.0411 (11)
H530.11920.35440.69380.049*
C540.1664 (6)0.2376 (3)0.7102 (2)0.0455 (12)
H540.29280.25370.70680.055*
C550.2409 (6)0.3346 (3)0.6927 (3)0.0437 (12)
O560.4000 (4)0.3139 (2)0.6908 (2)0.0655 (10)
O570.1533 (3)0.4160 (2)0.68678 (19)0.0510 (8)
H570.22730.44560.67680.077*
C580.4261 (5)0.6417 (3)0.6232 (3)0.0581 (14)
H580.37600.69780.61240.070*
C590.3117 (6)0.5920 (3)0.6401 (2)0.0467 (12)
H590.18600.61080.63670.056*
N600.3771 (5)0.5158 (3)0.6616 (3)0.0644 (13)
C610.5561 (6)0.4914 (4)0.6609 (4)0.085 (2)
H610.60370.43610.67380.102*
C620.6739 (6)0.5379 (3)0.6437 (3)0.0570 (14)
H620.79930.51790.64700.068*
C630.6062 (5)0.6168 (3)0.6207 (3)0.0465 (12)
C640.7277 (7)0.6679 (4)0.5991 (3)0.0597 (15)
O650.8967 (4)0.6356 (2)0.5947 (2)0.0712 (11)
C660.6626 (7)0.7517 (4)0.5710 (4)0.096 (2)
H66A0.76590.77510.55810.144*
H66B0.58770.79640.60930.144*
H66C0.59190.73810.52730.144*
C671.4501 (4)0.7286 (3)0.9038 (3)0.0476 (12)
H671.40060.78170.91980.057*
C681.3432 (6)0.6753 (4)0.8810 (3)0.0639 (16)
H681.21680.69570.87910.077*
N691.4050 (4)0.5984 (3)0.8619 (2)0.0462 (10)
C701.5831 (4)0.5709 (3)0.8584 (3)0.0481 (12)
H701.62850.51810.84130.058*
C711.7027 (5)0.6198 (3)0.8800 (3)0.0583 (15)
H711.82860.59870.87970.070*
C721.6374 (5)0.6978 (3)0.9013 (3)0.0466 (13)
C731.7685 (6)0.7522 (3)0.9251 (3)0.0497 (13)
O741.9232 (4)0.7263 (2)0.9260 (2)0.0743 (12)
C751.6874 (6)0.8395 (3)0.9400 (3)0.0584 (13)
H75A1.78210.86840.95330.088*
H75B1.60560.83140.98070.088*
H75C1.62040.87690.89590.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.049 (3)0.043 (3)0.055 (3)0.015 (2)0.001 (2)0.015 (2)
C20.059 (3)0.072 (4)0.049 (3)0.028 (3)0.014 (2)0.035 (3)
C30.075 (4)0.079 (4)0.041 (3)0.020 (3)0.005 (3)0.029 (3)
C40.038 (2)0.047 (3)0.042 (3)0.015 (2)0.005 (2)0.017 (2)
C50.056 (3)0.044 (3)0.025 (2)0.010 (2)0.0196 (19)0.000 (2)
C60.038 (2)0.033 (2)0.047 (3)0.0075 (19)0.012 (2)0.014 (2)
C70.053 (2)0.050 (3)0.028 (2)0.020 (2)0.0075 (18)0.019 (2)
C80.059 (3)0.046 (3)0.033 (3)0.009 (2)0.010 (2)0.005 (2)
C90.036 (2)0.037 (3)0.059 (3)0.002 (2)0.006 (2)0.019 (2)
C100.037 (2)0.037 (2)0.027 (2)0.0016 (18)0.0129 (17)0.0098 (19)
C110.041 (2)0.050 (3)0.034 (3)0.012 (2)0.0148 (19)0.016 (2)
C120.058 (3)0.066 (3)0.031 (3)0.032 (3)0.009 (2)0.008 (2)
C130.050 (3)0.059 (3)0.039 (3)0.025 (2)0.021 (2)0.014 (2)
C140.055 (3)0.055 (3)0.022 (2)0.019 (2)0.014 (2)0.013 (2)
C150.033 (2)0.047 (3)0.049 (3)0.014 (2)0.0096 (19)0.019 (2)
C160.048 (3)0.047 (3)0.034 (3)0.019 (2)0.012 (2)0.011 (2)
C170.049 (3)0.050 (3)0.066 (4)0.020 (2)0.028 (2)0.015 (3)
C180.043 (2)0.046 (3)0.053 (3)0.025 (2)0.021 (2)0.023 (2)
C190.045 (2)0.033 (2)0.028 (2)0.012 (2)0.0124 (18)0.0043 (19)
C200.031 (2)0.038 (3)0.044 (3)0.0142 (19)0.007 (2)0.008 (2)
N210.044 (2)0.043 (2)0.033 (2)0.0156 (18)0.0157 (16)0.0178 (18)
N220.0365 (19)0.035 (2)0.042 (2)0.0059 (16)0.0103 (16)0.0131 (18)
N230.046 (2)0.043 (2)0.043 (2)0.0154 (19)0.0094 (18)0.011 (2)
N240.043 (2)0.049 (2)0.031 (2)0.0232 (18)0.0198 (16)0.0122 (18)
C250.074 (3)0.050 (3)0.037 (3)0.022 (3)0.012 (2)0.006 (2)
C260.064 (3)0.079 (4)0.064 (4)0.025 (3)0.020 (3)0.030 (3)
C270.106 (4)0.059 (3)0.078 (4)0.016 (3)0.025 (4)0.038 (3)
N280.115 (4)0.123 (5)0.059 (3)0.026 (4)0.049 (3)0.029 (4)
C290.182 (8)0.119 (6)0.064 (5)0.059 (6)0.045 (5)0.011 (4)
C300.165 (6)0.109 (6)0.055 (4)0.001 (5)0.055 (4)0.004 (4)
C310.051 (3)0.029 (2)0.043 (3)0.021 (2)0.016 (2)0.016 (2)
C320.032 (2)0.029 (2)0.052 (3)0.0076 (19)0.0057 (19)0.012 (2)
C330.047 (3)0.032 (3)0.053 (3)0.003 (2)0.005 (2)0.007 (2)
C340.048 (3)0.033 (3)0.048 (3)0.011 (2)0.012 (2)0.013 (2)
C350.034 (3)0.049 (3)0.088 (4)0.008 (2)0.012 (2)0.034 (3)
C360.024 (2)0.042 (3)0.088 (4)0.011 (2)0.008 (2)0.022 (3)
C370.050 (3)0.050 (4)0.067 (4)0.016 (3)0.012 (3)0.018 (3)
O380.0258 (17)0.070 (3)0.101 (3)0.0149 (16)0.0026 (16)0.034 (2)
O390.044 (2)0.053 (2)0.139 (4)0.0201 (18)0.016 (2)0.041 (2)
C400.042 (2)0.079 (4)0.040 (3)0.027 (2)0.019 (2)0.029 (3)
C410.068 (3)0.115 (5)0.050 (4)0.018 (3)0.023 (3)0.023 (3)
C420.077 (4)0.181 (7)0.034 (3)0.003 (4)0.023 (3)0.033 (4)
C430.060 (3)0.104 (5)0.036 (3)0.052 (3)0.013 (2)0.032 (3)
C440.082 (3)0.101 (4)0.036 (3)0.036 (3)0.028 (2)0.022 (3)
C450.072 (3)0.064 (3)0.050 (3)0.028 (3)0.022 (2)0.023 (3)
C460.089 (3)0.094 (4)0.062 (3)0.033 (3)0.031 (2)0.032 (3)
O470.124 (3)0.145 (5)0.138 (4)0.024 (3)0.031 (3)0.058 (3)
O480.118 (3)0.089 (4)0.111 (3)0.030 (3)0.029 (3)0.029 (3)
C490.031 (2)0.063 (3)0.028 (3)0.011 (2)0.0064 (18)0.011 (2)
C500.038 (3)0.053 (3)0.046 (3)0.005 (2)0.010 (2)0.018 (2)
C510.019 (2)0.052 (3)0.052 (3)0.0062 (19)0.0134 (18)0.022 (2)
C520.019 (2)0.053 (3)0.050 (3)0.0095 (19)0.0021 (18)0.020 (2)
C530.036 (2)0.042 (3)0.052 (3)0.012 (2)0.006 (2)0.019 (2)
C540.040 (3)0.058 (3)0.046 (3)0.010 (2)0.020 (2)0.027 (2)
C550.030 (3)0.043 (3)0.061 (3)0.008 (2)0.011 (2)0.016 (3)
O560.048 (2)0.051 (2)0.105 (3)0.0118 (17)0.0171 (19)0.032 (2)
O570.0345 (16)0.048 (2)0.078 (2)0.0104 (15)0.0002 (15)0.0284 (18)
C580.050 (3)0.045 (3)0.078 (4)0.002 (2)0.014 (2)0.018 (3)
C590.031 (2)0.055 (3)0.057 (3)0.001 (2)0.009 (2)0.024 (3)
N600.038 (2)0.059 (3)0.098 (4)0.011 (2)0.019 (2)0.023 (3)
C610.048 (3)0.074 (4)0.139 (6)0.017 (3)0.017 (3)0.063 (4)
C620.045 (3)0.050 (3)0.081 (4)0.017 (3)0.015 (3)0.019 (3)
C630.043 (3)0.040 (3)0.061 (3)0.005 (2)0.019 (2)0.025 (2)
C640.052 (3)0.060 (4)0.063 (4)0.001 (3)0.019 (2)0.013 (3)
O650.046 (2)0.068 (2)0.108 (3)0.0177 (17)0.0177 (18)0.033 (2)
C660.059 (3)0.109 (5)0.136 (6)0.025 (3)0.046 (3)0.057 (4)
C670.026 (2)0.051 (3)0.070 (3)0.011 (2)0.0105 (19)0.020 (2)
C680.037 (3)0.057 (4)0.103 (5)0.016 (3)0.002 (3)0.023 (3)
N690.039 (2)0.050 (3)0.060 (3)0.0176 (19)0.0057 (17)0.027 (2)
C700.046 (3)0.037 (2)0.072 (3)0.028 (2)0.009 (2)0.018 (2)
C710.021 (2)0.052 (3)0.105 (5)0.008 (2)0.017 (2)0.022 (3)
C720.030 (2)0.056 (3)0.058 (3)0.021 (2)0.011 (2)0.011 (3)
C730.037 (3)0.050 (3)0.075 (3)0.029 (2)0.007 (2)0.022 (3)
O740.0269 (18)0.069 (2)0.136 (4)0.0196 (16)0.0065 (18)0.032 (2)
C750.047 (3)0.043 (3)0.099 (4)0.017 (2)0.003 (2)0.038 (2)
Geometric parameters (Å, º) top
C1—C201.358 (6)C36—H360.9500
C1—N211.415 (5)C37—O381.230 (5)
C1—C21.433 (6)C37—O391.280 (6)
C2—C31.328 (6)O39—H390.8400
C2—H20.9500C40—C411.3900
C3—C41.429 (6)C40—C451.3900
C3—H30.9500C41—C421.3900
C4—N211.373 (5)C41—H410.9500
C4—C51.406 (6)C42—C431.3900
C5—C61.355 (6)C42—H420.9500
C5—C251.513 (5)C43—C441.3900
C6—N221.376 (5)C43—C461.490 (4)
C6—C71.408 (6)C44—C451.3900
C7—C81.340 (6)C44—H440.9500
C7—H70.9500C45—H450.9500
C8—C91.427 (6)C46—O471.211 (6)
C8—H80.9500C46—O481.359 (2)
C9—N221.358 (5)O48—H480.8400
C9—C101.420 (6)C49—C541.392 (6)
C10—C111.431 (5)C49—C501.427 (5)
C10—C311.502 (6)C50—C511.392 (6)
C11—N231.381 (5)C50—H500.9500
C11—C121.405 (6)C51—C521.343 (6)
C12—C131.394 (6)C51—H510.9500
C12—H120.9500C52—C531.427 (5)
C13—C141.414 (6)C52—C551.486 (6)
C13—H130.9500C53—C541.356 (6)
C14—N231.386 (5)C53—H530.9500
C14—C151.412 (5)C54—H540.9500
C15—C161.436 (6)C55—O561.188 (5)
C15—C401.471 (5)C55—O571.344 (5)
C16—N241.365 (5)O57—H570.8400
C16—C171.517 (6)C58—C631.347 (2)
C17—C181.325 (6)C58—C591.353 (6)
C17—H170.9500C58—H580.9500
C18—C191.488 (5)C59—N601.342 (6)
C18—H180.9500C59—H590.9500
C19—C201.369 (6)N60—C611.339 (5)
C19—N241.381 (5)C61—C621.338 (7)
C20—C491.529 (6)C61—H610.9500
N21—H210.8800C62—C631.397 (6)
N22—H220.8800C62—H620.9500
N23—H230.8800C63—C641.443 (7)
N24—H240.8800C64—O651.282 (5)
C25—C301.348 (2)C64—C661.510 (7)
C25—C261.384 (5)C66—H66A0.9800
C26—C271.363 (5)C66—H66B0.9800
C26—H260.9500C66—H66C0.9800
C27—N281.315 (2)C67—C681.399 (6)
C27—H270.9500C67—C721.415 (4)
N28—C291.308 (7)C67—H670.9500
C29—C301.397 (6)C68—N691.325 (6)
C29—H290.9500C68—H680.9500
C30—H300.9500N69—C701.3444 (19)
C31—C321.375 (5)C70—C711.408 (6)
C31—C361.405 (6)C70—H700.9500
C32—C331.384 (6)C71—C721.365 (6)
C32—H320.9500C71—H710.9500
C33—C341.438 (6)C72—C731.552 (6)
C33—H330.9500C73—O741.166 (5)
C34—C351.358 (5)C73—C751.470 (6)
C34—C371.499 (6)C75—H75A0.9800
C35—C361.385 (6)C75—H75B0.9800
C35—H350.9500C75—H75C0.9800
C20—C1—N21124.7 (4)C36—C35—H35118.7
C20—C1—C2130.3 (4)C35—C36—C31118.4 (4)
N21—C1—C2105.1 (4)C35—C36—H36120.8
C3—C2—C1108.9 (4)C31—C36—H36120.8
C3—C2—H2125.5O38—C37—O39123.3 (5)
C1—C2—H2125.5O38—C37—C34124.4 (5)
C2—C3—C4110.1 (5)O39—C37—C34112.2 (4)
C2—C3—H3124.9C37—O39—H39109.5
C4—C3—H3124.9C41—C40—C45120.0
N21—C4—C5124.5 (4)C41—C40—C15120.4 (3)
N21—C4—C3105.8 (4)C45—C40—C15119.6 (3)
C5—C4—C3129.6 (4)C40—C41—C42120.0
C6—C5—C4129.6 (4)C40—C41—H41120.0
C6—C5—C25117.6 (4)C42—C41—H41120.0
C4—C5—C25112.8 (4)C43—C42—C41120.0
C5—C6—N22125.3 (4)C43—C42—H42120.0
C5—C6—C7125.4 (4)C41—C42—H42120.0
N22—C6—C7109.3 (4)C42—C43—C44120.0
C8—C7—C6109.3 (4)C42—C43—C46125.2 (3)
C8—C7—H7125.4C44—C43—C46114.8 (3)
C6—C7—H7125.4C45—C44—C43120.0
C7—C8—C9104.7 (4)C45—C44—H44120.0
C7—C8—H8127.7C43—C44—H44120.0
C9—C8—H8127.7C44—C45—C40120.0
N22—C9—C10124.8 (4)C44—C45—H45120.0
N22—C9—C8111.8 (4)C40—C45—H45120.0
C10—C9—C8123.4 (4)O47—C46—O48120.3 (5)
C9—C10—C11124.0 (4)O47—C46—C43120.2 (5)
C9—C10—C31119.8 (4)O48—C46—C43119.6 (4)
C11—C10—C31116.1 (3)C46—O48—H48109.5
N23—C11—C12108.1 (4)C54—C49—C50117.7 (4)
N23—C11—C10125.3 (4)C54—C49—C20123.0 (4)
C12—C11—C10126.6 (4)C50—C49—C20119.3 (4)
C13—C12—C11108.2 (4)C51—C50—C49118.2 (4)
C13—C12—H12125.9C51—C50—H50120.9
C11—C12—H12125.9C49—C50—H50120.9
C12—C13—C14106.9 (4)C52—C51—C50122.9 (4)
C12—C13—H13126.6C52—C51—H51118.5
C14—C13—H13126.5C50—C51—H51118.5
N23—C14—C15127.3 (4)C51—C52—C53119.5 (4)
N23—C14—C13108.3 (4)C51—C52—C55120.8 (4)
C15—C14—C13124.4 (4)C53—C52—C55119.8 (4)
C14—C15—C16123.5 (4)C54—C53—C52118.3 (4)
C14—C15—C40118.7 (4)C54—C53—H53120.8
C16—C15—C40117.7 (3)C52—C53—H53120.8
N24—C16—C15127.3 (4)C53—C54—C49123.3 (4)
N24—C16—C17110.5 (4)C53—C54—H54118.3
C15—C16—C17122.2 (4)C49—C54—H54118.3
C18—C17—C16105.7 (4)O56—C55—O57123.1 (4)
C18—C17—H17127.2O56—C55—C52121.4 (4)
C16—C17—H17127.2O57—C55—C52115.5 (4)
C17—C18—C19107.9 (4)C55—O57—H57109.5
C17—C18—H18126.1C63—C58—C59124.3 (5)
C19—C18—H18126.1C63—C58—H58117.9
C20—C19—N24125.9 (4)C59—C58—H58117.8
C20—C19—C18124.1 (4)N60—C59—C58119.6 (4)
N24—C19—C18110.0 (4)N60—C59—H59120.2
C1—C20—C19126.8 (4)C58—C59—H59120.2
C1—C20—C49114.7 (4)C59—N60—C61116.5 (5)
C19—C20—C49117.9 (4)C62—C61—N60125.8 (5)
C4—N21—C1110.1 (3)C62—C61—H61117.1
C4—N21—H21124.9N60—C61—H61117.1
C1—N21—H21125.0C61—C62—C63117.8 (4)
C9—N22—C6104.9 (3)C61—C62—H62121.1
C9—N22—H22127.6C63—C62—H62121.1
C6—N22—H22127.6C58—C63—C62115.8 (4)
C14—N23—C11108.4 (4)C58—C63—C64124.2 (4)
C14—N23—H23125.8C62—C63—C64120.0 (4)
C11—N23—H23125.8O65—C64—C63119.1 (4)
C16—N24—C19105.9 (3)O65—C64—C66118.0 (5)
C16—N24—H24127.0C63—C64—C66122.3 (4)
C19—N24—H24127.0C64—C66—H66A109.5
C30—C25—C26115.3 (4)C64—C66—H66B109.4
C30—C25—C5122.8 (4)H66A—C66—H66B109.5
C26—C25—C5121.9 (4)C64—C66—H66C109.5
C27—C26—C25122.2 (4)H66A—C66—H66C109.5
C27—C26—H26118.9H66B—C66—H66C109.5
C25—C26—H26118.9C68—C67—C72115.1 (4)
N28—C27—C26121.6 (4)C68—C67—H67122.5
N28—C27—H27119.2C72—C67—H67122.4
C26—C27—H27119.2N69—C68—C67124.9 (4)
C29—N28—C27117.3 (4)N69—C68—H68117.5
N28—C29—C30123.7 (5)C67—C68—H68117.5
N28—C29—H29118.2C68—N69—C70119.2 (4)
C30—C29—H29118.2N69—C70—C71120.3 (4)
C25—C30—C29119.6 (4)N69—C70—H70119.9
C25—C30—H30120.2C71—C70—H70119.9
C29—C30—H30120.2C72—C71—C70119.8 (4)
C32—C31—C36119.5 (4)C72—C71—H71120.1
C32—C31—C10123.7 (4)C70—C71—H71120.1
C36—C31—C10116.8 (4)C71—C72—C67120.5 (4)
C31—C32—C33122.7 (4)C71—C72—C73120.1 (4)
C31—C32—H32118.7C67—C72—C73119.4 (4)
C33—C32—H32118.7O74—C73—C75122.9 (4)
C32—C33—C34117.2 (4)O74—C73—C72120.5 (4)
C32—C33—H33121.4C75—C73—C72116.4 (4)
C34—C33—H33121.4C73—C75—H75A109.5
C35—C34—C33119.6 (4)C73—C75—H75B109.5
C35—C34—C37123.8 (4)H75A—C75—H75B109.5
C33—C34—C37116.6 (4)C73—C75—H75C109.5
C34—C35—C36122.6 (4)H75A—C75—H75C109.5
C34—C35—H35118.7H75B—C75—H75C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O39—H39···N690.841.822.653 (4)172
O57—H57···N600.841.792.630 (5)175
O48—H48···N28i0.841.772.596 (5)167
C29—H29···O47ii0.952.683.273 (8)121
C61—H61···O560.952.753.375 (7)124
C70—H70···O380.952.613.221 (5)123
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y, z1.

Experimental details

(I)(II)
Crystal data
Chemical formulaC46H29N5O6·2.5C2H6SOC46H29N5O6·2C7H7NO·10C4H8O
Mr943.061711.05
Crystal system, space groupMonoclinic, CcTriclinic, P1
Temperature (K)110110
a, b, c (Å)6.5978 (3), 29.2458 (15), 28.6630 (13)7.6005 (3), 15.6609 (10), 18.6149 (12)
α, β, γ (°)90, 90.521 (2), 9077.718 (3), 89.630 (4), 78.805 (4)
V3)5530.5 (5)2122.4 (2)
Z41
Radiation typeMo KαMo Kα
µ (mm1)0.170.09
Crystal size (mm)0.40 × 0.20 × 0.030.40 × 0.30 × 0.25
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18496, 11808, 6211 24317, 10109, 4725
Rint0.0710.060
(sin θ/λ)max1)0.6570.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.085, 0.211, 1.06 0.052, 0.135, 0.80
No. of reflections1180810109
No. of parameters594669
No. of restraints28
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.83, 0.310.25, 0.20
Absolute structureFlack (1983), 5242 Friedel pairs?
Absolute structure parameter0.42 (12)?

Computer programs: Collect (Nonius, 1999), DENZO (Otwinowski & Minor, 1997), DENZO, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006), SHELXL97.

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O56—H56···O590.841.782.565 (6)154
O48—H48···O630.841.822.599 (5)154
O39—H39···O63i0.841.792.624 (5)169
C17—H17···N28ii0.952.553.387 (6)147
Symmetry codes: (i) x1, y+1, z1/2; (ii) x+1/2, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O39—H39···N690.841.822.653 (4)172
O57—H57···N600.841.792.630 (5)175
O48—H48···N28i0.841.772.596 (5)167
C29—H29···O47ii0.952.683.273 (8)121
C61—H61···O560.952.753.375 (7)124
C70—H70···O380.952.613.221 (5)123
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y, z1.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds