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The title free base porphyrin compound forms hydrogen-bonded adducts with N,N-dimethyl­formamide, C44H30N4O4·4C3H7NO, (I), a mixture of N,N-dimethyl­formamide and water, C44H30N4O4·4C3H7NO·H2O, (II), and a mixture of N,N-dimethyl­acetamide and water, C44H30N4O4·6C3H7NO·2H2O, (III). Total solvation of the four hydroxy functions of the porphyrin molecules characterizes all three compounds, thus preventing its supra­molecular association into extended network architectures. In (I), the asymmetric unit consist of two five-component adduct species, while in (III), the nine-component entities reside on centres of inversion. This report provides the first structural characterizations of the free base tetra­(hydroxy­phenyl)porphyrin. It also demonstrates that the presence of strong Lewis bases, such as dimethyl­formamide or dimethyl­acetamide, in the crystallization mixture prevents direct supra­molecular networking of the porphyrin ligands via O—H...O—H hydrogen bonds, due to their competing O—H...N(base) inter­action with the hydroxy functions. The crystal packing of compounds (I)–(III) resembles that of other hydrogen-bonding-assisted tetra­aryl­porphyrin clathrates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108040018/gd3260sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108040018/gd3260Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108040018/gd3260IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108040018/gd3260IIIsup4.hkl
Contains datablock III

CCDC references: 718117; 718118; 718119

Comment top

Porphyrin macrocycles tetra-substituted with 4-hydroxyphenyl groups at their meso positions (TOHPP) provide a classical example of an organic moiety with multiple complementary terminal functional groups directed at four diverging directions of the equatorial molecular plane that exhibits a high propensity for self-assembling into flat hydrogen-bonded two-dimensional nets (Goldberg, 2002, 2005). It has been shown that the hydroxy substituents may engage readily in O—H···O—H supramolecular synthons, leading to the formation of extended multiporphyrin arrays. Suitable examples include the zinc-metallated porphyrin Zn-TOHPP platform (Goldberg et al., 1995). In some cases, water species are incorporated into the hydrogen-bonding patterns, bridging neighbouring porphyrin units while preserving the two-dimensional connectivity scheme. In this study, we attempted to use free base TOHPP building blocks in reactions with heavy metal ions as possible interporphyrin connectors under solvothermal conditions, following our earlier successful results to this end with the tetra(4-carboxyphenyl)porphyrin (TCPP) isomer (Goldberg, 2008). These reactions were carried out in a dimethylformamide–water or dimethylacetamide–water solvent environment, as hydrolysis of the amide was found to promote the synthesis of metal–organic frameworks (Burrows et al., 2005; Lipstman et al., 2007; Muniappan et al., 2007). These solvent mixtures are then capable of solubilizing the TOHPP and engaging it in the supramolecular reaction. On the other hand, it is also well documented that the networking of functionalized porphyrin moieties, both via direct intermolecular hydrogen bonding or by intercoordination through bridging metal ions, can be disrupted readily by competing solvation that may prevent supramolecular association. This is common with strong Lewis base reagents, for example dimethylformamide, dimethyl sulfoxide and pyridine, which have rather strong proton affinity for the hydroxylic acid H atom (Lipstman et al., 2006; George et al., 2006). Indeed, present efforts to prepare TOHPP-based extended supramolecular architectures, either by O—H···O—H or O—H···metal···O—H interactions, in the given experimental conditions have failed. Instead, the products obtained represent totally solvated discrete porphyrin–solvent assemblies, held together by hydrogen bonds between the tetradentate porphyrin and the surrounding components, rather than extended network arrays. Similar observations have been reported for the TCPP platform (Lipstman et al., 2006; George et al., 2006).

Within the above context, we describe here the structures of the solid products obtained by crystallizing TOHPP from a mixture of dimethylformamide and water, (I) and (II), and dimethylacetamide and water, (III). The molecular structures of (I)–(III) are shown in Figs. 1–3, respectively. In all cases, various lanthanide salts were also present in the solvothermal reactors, but not incorporated into the crystalline products.

Although compounds (I) and (II) were obtained from crystallization mixtures of similar composition, they represent differently structured adducts. In (I), the TOHPP unit is hydrogen-bonded at the four corners of its molecular framework to a dimethylformamide species, forming a pentameric assembly, without incorporation of any water molecule into the structure (Table 1). The asymmetric unit contains two such adduct assemblies of slightly different geometry and partial disorder of the terminal amide species (Fig. 1).

A different composition (TOHPP:dimethylformamide:water 1:4:1) and connectivity scheme characterizes adduct (II). Here, only three of the OH groups (atoms O31, O45 and O52) form hydrogen bonds directly to the adjacent amide species, while the fourth hydroxyl site (atom O38) interacts with another amide molecule through an intervening water molecule (O73) (Fig. 2 and Table 2).

In (III), the porphyrin:dimethylacetamide:water composition is 1:6:2, and the entire nine-component hydrogen-bonded entity is located on inversion (Fig. 3). The two inversion-related O26 hydroxyl groups form direct O—H···O(C) hydrogen bonds with the amides. On the other hand, each of the O19 hydroxyl groups forms hydrogen bonds to a water molecule (O27) first, which then donates its two H atoms to the carbonyl groups of two other units of the dimethylacetamide, atoms O28 and O34 (Table 3).

As expected, the conformation of the free base porphyrin macrocycle is significantly distorted from planarity in spite of its aromatic nature. This should be attributed to the repulsion between the inner pyrrole H atoms. In (I) and (II) a marked saddle-type distortion from planarity characterizes the conformation of the porphyrin core (Fig. 4a and b). A somewhat smaller distortion is observed in (III), but it is still evident from Fig. 4(c) that the inner pyrrole H atoms avoid each other as much as possible. The inner pyrrole H atoms could not be located from experimental data, which prevents a detailed discussion of this feature. It can only be said that the observed deformations are such that the minimum distance between the two H atoms (with the assumed N—H `X-ray' bond length of 0.88 Å) across the porphyrin core is at least 2.3 Å.

The observed crystal packing in compounds (I)–(III) is charateristic of the vast number of porphyrin `sponges' and clathrates, whether of purely van der Waals or hydrogen bonding-assisted types, reported previously (e.g. Byrn et al., 1993, and references therein). It generally consists of alternating (columnar or layered) zones of offset-stacked porphyrin moieties and molecules of the solvent. This is nicely demonstrated in Fig. 5, which depicts an intercalating type of molecular organization in (III).

In summary, this study describes the effects of competing solvation on the self-assembly of TOHPP-type porphyrin building blocks by hydrogen bonding, where solvent components bearing dominant (in the amide entities) or comparable (in the water solvent) H-atom accepting capacity interfere with the direct assembly of the porphyrin units into supramolecular porphyrin arrays. It also reports for the first time crystal structures of the free base TOHPP entity.

Experimental top

TOHPP and all solvents used were obtained commercially. They were reacted together (with various lanthanide salts) [Please give reagents and their quantities for each of (I)–(III)] in a sealed reactor at 423 K for about 50 h, and then gradually cooled down to ambient temperature. [Please give details of recrystallisation here]

Refinement top

C-bound H atoms were located in calculated positions and constrained to ride on their parent atoms, with C—H = 0.95 or 0.98 Å and with Uiso(H) = 1.2 or 1.5Ueq(C). H atoms bound to O atoms were either located in difference Fourier maps or placed in calculated positions to correspond to idealized hydrogen-bonding geometries, with O—H = 0.84 Å for porphyrin O atoms or O—H = 0.89–0.96 Å for water O atoms. Their atomic positions were not refined, and they were constrained to ride on their parent atoms with Uiso(H) = 1.5Ueq(O). In (I), some of the dimethylformamide components are disordered, namely O115—C119 and O140—C144. The C(methyl) atoms of the former species show large-amplitude displacement parameters, while the latter moiety reveals a twofold orientational disorder. DELU restraints (SHELXL97; Sheldrick, 2008) were applied to the displacement parameters of the atoms O140—C144, and DFIX restraints (SHELXL97) were applied to the N117—C118 and N117—C119 bonds. Restraint-free least-squares refinements were applied to structures (II) and (III). In all three structures, the two H atoms bound to N within the porphyrin core could not be located reliably. As some residual electron density was observed near all the pyrrole N atoms, the H atoms bound to them were assumed to be disordered equally between the four pyrrole rings and were located in calculated positions, with N—H = 0.88 Å and Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: [Please provide details] for (I); COLLECT (Nonius, 1999) for (II), (III). Cell refinement: [Please provide details] for (I); DENZO (Otwinowski & Minor, 1997) for (II), (III). Data reduction: [Please provide details] for (I); DENZO (Otwinowski & Minor, 1997) for (II), (III). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SIR97 (Altomare et al., 1994) for (II), (III). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: ORTEPIII (Burnett & Johnson, 1996) for (I); ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006) for (II), (III). Software used to prepare material for publication: [Please provide details] for (I); SHELXL97 (Sheldrick, 2008) for (II), (III).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the atom-labelling scheme of the two crystallographically independent entities in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level at ca 110 K. H atoms have been omitted, except for those involved in intermolecular hydrogen bonds (dotted lines). Only one orientation of the disordered dimethylformamide species is shown.
[Figure 2] Fig. 2. The molecular structure of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level at ca 110 K. H atoms have been omitted, except for those involved in intermolecular hydrogen bonds (dotted lines).
[Figure 3] Fig. 3. The molecular structure of compound (III), showing the atom-labelling scheme. The molecule resides on crystallographic inversion, and only the asymmetric unit is labelled. Displacement ellipsoids are drawn at the 50% probability level at ca 110 K. H atoms have been omitted, except for those involved in intermolecular hydrogen bonds (dotted lines).
[Figure 4] Fig. 4. Ball-and-stick representations of the porphyrin entities in (a) (I) (only one of the two units is shown, as both have very similar conformations), (b) (II) and (c) (III). The igures show the saddle-type distortion of the porphyrin cores from planarity in (I) and (II), and to a lesser extent in (III), which is required to minimize repulsion between the inner pyrrole H atoms.
[Figure 5] Fig. 5. The crystal structure of (III). Water molecules are indicated by small spheres. H atoms have been omitted. Note the seggregation between the porphyrin and solvent zones in the structure.
(I) 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin N,N'-dimethylformamide tetrasolvate top
Crystal data top
C44H30N4O4·4C3H7NOZ = 4
Mr = 971.10F(000) = 2056
Triclinic, P1Dx = 1.282 Mg m3
a = 13.6255 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.0184 (3) ÅCell parameters from 14137 reflections
c = 26.2466 (5) Åθ = 2.4–27.9°
α = 101.7445 (12)°µ = 0.09 mm1
β = 92.4786 (12)°T = 110 K
γ = 114.9158 (8)°Prism, red
V = 5032.65 (15) Å30.40 × 0.40 × 0.20 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
13053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Graphite monochromatorθmax = 27.9°, θmin = 2.4°
Detector resolution: 12.8 pixels mm-1h = 1717
0.7 deg. ϕ and ω scank = 2119
50610 measured reflectionsl = 3434
23879 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: full with fixed elements per cycleSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0777P)2 + 0.4228P]
where P = (Fo2 + 2Fc2)/3
23877 reflections(Δ/σ)max = 0.043
1370 parametersΔρmax = 0.36 e Å3
18 restraintsΔρmin = 0.39 e Å3
Crystal data top
C44H30N4O4·4C3H7NOγ = 114.9158 (8)°
Mr = 971.10V = 5032.65 (15) Å3
Triclinic, P1Z = 4
a = 13.6255 (2) ÅMo Kα radiation
b = 16.0184 (3) ŵ = 0.09 mm1
c = 26.2466 (5) ÅT = 110 K
α = 101.7445 (12)°0.40 × 0.40 × 0.20 mm
β = 92.4786 (12)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
13053 reflections with I > 2σ(I)
50610 measured reflectionsRint = 0.051
23879 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06318 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.04Δρmax = 0.36 e Å3
23877 reflectionsΔρmin = 0.39 e Å3
1370 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.

Two of the DMF species exhibit partial orientational disorder.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.61879 (17)0.21510 (15)0.02696 (8)0.0300 (5)
C20.59874 (18)0.27621 (16)0.06191 (9)0.0327 (5)
H20.53140.32900.06190.039*
C30.69292 (17)0.24576 (15)0.09538 (9)0.0305 (5)
H30.70250.27440.12240.037*
C40.77472 (17)0.16381 (15)0.08320 (8)0.0286 (5)
C50.88423 (17)0.11179 (15)0.10765 (8)0.0271 (5)
C60.96081 (17)0.02768 (14)0.09677 (8)0.0256 (5)
C71.07468 (17)0.02043 (15)0.12080 (8)0.0288 (5)
H71.10960.00040.14410.035*
C81.12116 (18)0.10006 (15)0.10368 (8)0.0297 (5)
H81.19550.14600.11210.036*
C91.03541 (16)0.10209 (15)0.06969 (8)0.0261 (5)
C101.04947 (17)0.17895 (14)0.04780 (8)0.0262 (5)
C110.97072 (17)0.17679 (14)0.01049 (8)0.0260 (5)
C120.97341 (18)0.25182 (15)0.01101 (8)0.0315 (5)
H121.02840.31560.00120.038*
C130.88389 (18)0.21714 (15)0.04818 (9)0.0321 (5)
H130.86640.25230.06910.039*
C140.82122 (17)0.11944 (15)0.05031 (8)0.0280 (5)
C150.72287 (17)0.05659 (15)0.08390 (8)0.0269 (5)
C160.65282 (17)0.03429 (15)0.07889 (8)0.0270 (5)
C170.55465 (17)0.09913 (15)0.11573 (8)0.0299 (5)
H170.53050.08950.14760.036*
C180.50511 (17)0.17472 (15)0.09627 (8)0.0302 (5)
H180.43830.22900.11130.036*
C190.57304 (17)0.15796 (15)0.04771 (8)0.0280 (5)
C200.54700 (17)0.22266 (15)0.01533 (8)0.0284 (5)
N210.72647 (13)0.14720 (12)0.04161 (7)0.0278 (4)
H210.75930.10030.02650.033*0.50
N220.93977 (13)0.02141 (12)0.06458 (6)0.0256 (4)
H220.87780.00480.04460.031*0.50
N230.87501 (13)0.09771 (12)0.01321 (6)0.0269 (4)
H230.85190.04200.00570.032*0.50
N240.66334 (14)0.07297 (12)0.03854 (7)0.0278 (4)
H240.71710.04830.01210.033*0.50
C250.91760 (16)0.14762 (15)0.15054 (8)0.0265 (5)
C260.91509 (16)0.23755 (15)0.14060 (8)0.0277 (5)
H260.89510.27580.10560.033*
C270.94123 (17)0.27189 (15)0.18083 (8)0.0293 (5)
H270.93950.33310.17340.035*
C280.97014 (18)0.21653 (16)0.23233 (8)0.0319 (5)
C290.97521 (19)0.12630 (16)0.24263 (9)0.0353 (6)
H290.99670.08760.27750.042*
C300.94908 (18)0.09262 (16)0.20216 (9)0.0327 (5)
H300.95260.03070.20970.039*
O310.99382 (15)0.24738 (12)0.27390 (6)0.0445 (4)
H310.99240.30100.26290.067*
C321.15291 (17)0.26854 (15)0.06517 (8)0.0276 (5)
C331.19204 (17)0.31202 (15)0.11834 (8)0.0302 (5)
H331.15080.28540.14410.036*
C341.29018 (18)0.39354 (16)0.13428 (9)0.0343 (5)
H341.31650.42110.17070.041*
C351.35007 (18)0.43495 (16)0.09718 (9)0.0336 (5)
C361.31099 (18)0.39416 (15)0.04412 (9)0.0323 (5)
H361.35060.42280.01850.039*
C371.21429 (17)0.31176 (15)0.02854 (9)0.0293 (5)
H371.18900.28390.00790.035*
O381.44719 (12)0.51479 (11)0.11023 (6)0.0423 (4)
H381.45590.54060.14240.064*
C390.69269 (17)0.09163 (15)0.12792 (8)0.0289 (5)
C400.75866 (18)0.11138 (15)0.16746 (8)0.0317 (5)
H400.82400.10370.16560.038*
C410.73102 (18)0.14171 (15)0.20897 (9)0.0323 (5)
H410.77620.15310.23580.039*
C420.63652 (18)0.15566 (15)0.21169 (8)0.0310 (5)
C430.57107 (18)0.13768 (15)0.17246 (9)0.0334 (5)
H430.50670.14700.17390.040*
C440.59911 (18)0.10612 (15)0.13109 (9)0.0322 (5)
H440.55350.09420.10450.039*
O450.60583 (13)0.18700 (12)0.25092 (6)0.0392 (4)
H450.64960.19280.27300.059*
C460.43552 (17)0.30437 (15)0.02774 (8)0.0298 (5)
C470.34242 (18)0.28926 (17)0.02427 (9)0.0355 (5)
H470.35020.22650.01190.043*
C480.23823 (18)0.36421 (16)0.03863 (9)0.0383 (6)
H480.17550.35270.03570.046*
C490.22627 (18)0.45629 (16)0.05729 (9)0.0370 (6)
C500.31747 (19)0.47270 (17)0.06056 (9)0.0375 (6)
H500.30940.53560.07280.045*
C510.42128 (18)0.39741 (16)0.04595 (9)0.0345 (5)
H510.48370.40950.04840.041*
O520.12573 (13)0.53295 (11)0.07239 (7)0.0489 (5)
H520.07650.51460.06850.073*
C530.68522 (17)0.19749 (14)0.53673 (8)0.0274 (5)
C540.65216 (17)0.25367 (15)0.57406 (8)0.0302 (5)
H540.66840.30510.57630.036*
C550.59317 (17)0.22092 (15)0.60609 (8)0.0291 (5)
H550.56180.24540.63460.035*
C560.58649 (17)0.14332 (14)0.58941 (8)0.0261 (5)
C570.52688 (17)0.09328 (14)0.60857 (8)0.0257 (5)
C580.52863 (16)0.01452 (14)0.59219 (8)0.0244 (5)
C590.45810 (17)0.03071 (15)0.60819 (8)0.0274 (5)
H590.40090.00990.62880.033*
C600.48911 (17)0.10720 (15)0.58836 (8)0.0266 (5)
H600.45780.15070.59190.032*
C610.57999 (16)0.11073 (14)0.56034 (8)0.0243 (5)
C620.64071 (16)0.18640 (14)0.53791 (8)0.0247 (5)
C630.71602 (16)0.18449 (14)0.50345 (8)0.0243 (5)
C640.78337 (17)0.25826 (15)0.48018 (8)0.0277 (5)
H640.78900.32080.48700.033*
C650.83805 (17)0.22336 (15)0.44656 (8)0.0275 (5)
H650.88730.25710.42530.033*
C660.80923 (16)0.12783 (14)0.44855 (8)0.0249 (5)
C670.84372 (16)0.06436 (14)0.41913 (8)0.0247 (5)
C680.82273 (17)0.02531 (15)0.42703 (8)0.0261 (5)
C690.85031 (17)0.09367 (15)0.39272 (8)0.0287 (5)
H690.88110.08680.36120.034*
C700.82414 (17)0.16784 (15)0.41412 (8)0.0297 (5)
H700.83320.22350.40090.036*
C710.77898 (16)0.14656 (15)0.46164 (8)0.0264 (5)
C720.74315 (17)0.20860 (14)0.49527 (8)0.0266 (5)
N730.64570 (14)0.13032 (12)0.54814 (7)0.0269 (4)
H730.65680.08550.53140.032*0.50
N740.59926 (13)0.03393 (12)0.56140 (6)0.0246 (4)
H740.64720.01880.54560.030*0.50
N750.73667 (13)0.10787 (12)0.48453 (6)0.0250 (4)
H750.70780.05380.49400.030*0.50
N760.77646 (14)0.06087 (12)0.46786 (6)0.0257 (4)
H760.75050.03400.49290.031*0.50
C770.45933 (17)0.12610 (15)0.65029 (8)0.0260 (5)
C780.38117 (17)0.21947 (15)0.64357 (8)0.0290 (5)
H780.36810.26380.61090.035*
C790.32181 (18)0.24938 (16)0.68347 (9)0.0322 (5)
H790.26880.31350.67800.039*
C800.34002 (19)0.18567 (17)0.73120 (9)0.0349 (5)
C810.41514 (19)0.09244 (17)0.73836 (9)0.0360 (6)
H810.42650.04820.77080.043*
C820.47429 (18)0.06275 (16)0.69866 (8)0.0314 (5)
H820.52600.00180.70430.038*
O830.28428 (15)0.21110 (12)0.77211 (7)0.0502 (5)
H830.24820.27040.76510.075*
C840.62616 (16)0.27508 (14)0.55246 (8)0.0249 (5)
C850.64041 (17)0.32174 (14)0.60527 (8)0.0285 (5)
H850.65970.29670.63180.034*
C860.62684 (17)0.40429 (15)0.61963 (9)0.0304 (5)
H860.63660.43480.65580.036*
C870.59914 (17)0.44229 (15)0.58150 (9)0.0297 (5)
C880.58501 (17)0.39694 (15)0.52870 (9)0.0298 (5)
H880.56620.42240.50220.036*
C890.59836 (17)0.31466 (15)0.51486 (8)0.0280 (5)
H890.58830.28420.47870.034*
O900.58397 (13)0.52276 (10)0.59353 (6)0.0372 (4)
H900.59450.54370.62630.056*
C910.90542 (17)0.09415 (14)0.37538 (8)0.0265 (5)
C920.85944 (17)0.11683 (14)0.33468 (8)0.0272 (5)
H920.78960.11620.33610.033*
C930.91321 (18)0.14012 (15)0.29254 (8)0.0289 (5)
H930.88020.15510.26530.035*
C941.01525 (18)0.14161 (15)0.28992 (8)0.0289 (5)
C951.06301 (18)0.12016 (15)0.33039 (8)0.0295 (5)
H951.13320.12140.32890.035*
C961.00920 (17)0.09709 (14)0.37249 (8)0.0278 (5)
H961.04290.08300.39990.033*
O971.07319 (12)0.16468 (12)0.24952 (6)0.0375 (4)
H971.03710.17670.22770.056*
C980.76603 (18)0.29356 (15)0.48330 (8)0.0284 (5)
C990.87117 (18)0.28551 (16)0.49110 (9)0.0320 (5)
H990.92930.22570.50830.038*
C1000.89357 (19)0.36270 (16)0.47434 (9)0.0354 (5)
H1000.96600.35590.48070.042*
C1010.80946 (19)0.44999 (16)0.44826 (9)0.0350 (5)
C1020.70376 (19)0.45984 (16)0.44076 (10)0.0386 (6)
H1020.64570.51980.42370.046*
C1030.68254 (19)0.38250 (16)0.45813 (9)0.0362 (6)
H1030.60960.39010.45280.043*
O1040.82705 (14)0.52767 (11)0.42967 (8)0.0516 (5)
H1040.89460.51100.43080.077*
O1050.95763 (14)0.19200 (12)0.17650 (6)0.0401 (4)
C1060.8681 (2)0.12415 (19)0.15637 (9)0.0390 (6)
H1060.85090.06600.16600.047*
N1070.79474 (17)0.12642 (15)0.12250 (8)0.0410 (5)
C1080.6892 (2)0.0453 (2)0.10305 (12)0.0579 (8)
H10A0.68550.00760.11750.087*
H10B0.68000.02620.06460.087*
H10C0.63090.06240.11400.087*
C1090.8147 (2)0.2122 (2)0.10593 (11)0.0535 (7)
H10D0.77310.24290.12450.080*
H10E0.79160.19640.06790.080*
H10F0.89290.25560.11420.080*
O1100.74352 (13)0.21603 (12)0.32175 (6)0.0411 (4)
C1110.77188 (19)0.15508 (19)0.34392 (9)0.0386 (6)
H1110.73680.09380.33730.046*
N1120.84610 (16)0.16795 (15)0.37567 (8)0.0425 (5)
C1130.8782 (2)0.0934 (2)0.39607 (11)0.0623 (8)
H11A0.83150.03570.38550.094*
H11B0.95470.11380.38190.094*
H11C0.87020.08040.43450.094*
C1140.9056 (2)0.2592 (2)0.38730 (10)0.0571 (8)
H11D0.86640.29800.37820.086*
H11E0.91200.25000.42490.086*
H11F0.97890.29140.36670.086*
O1150.99135 (15)0.41564 (12)0.24325 (8)0.0568 (5)
C1161.0740 (2)0.42251 (19)0.25599 (10)0.0478 (7)
H1161.12800.37120.28210.057*
N1171.09516 (17)0.49425 (15)0.23698 (8)0.0561 (6)
C1181.0171 (2)0.57691 (17)0.19583 (11)0.0705 (9)
H11G0.94640.57460.19260.106*
H11H1.00770.63560.20550.106*
H11I1.04550.57540.16220.106*
C1191.2039 (3)0.4898 (4)0.25047 (17)0.135 (2)
H11J1.24340.48290.22010.203*
H11K1.19510.54830.26010.203*
H11L1.24550.43530.28020.203*
O1200.02141 (14)0.46403 (12)0.05977 (8)0.0560 (5)
C1210.1209 (2)0.50605 (17)0.06123 (10)0.0438 (6)
H1210.15200.48060.03420.053*
N1220.18868 (16)0.58286 (13)0.09657 (8)0.0404 (5)
C1230.1491 (2)0.62549 (19)0.13972 (10)0.0556 (7)
H12A0.07340.58200.14130.083*
H12B0.19500.63820.17280.083*
H12C0.15200.68520.13430.083*
C1240.3042 (2)0.62999 (19)0.09290 (12)0.0546 (7)
H12D0.32120.59280.06310.082*
H12E0.32270.69340.08760.082*
H12F0.34700.63560.12550.082*
O1251.48787 (15)0.61304 (13)0.20928 (7)0.0564 (5)
C1261.5524 (2)0.69725 (19)0.21336 (10)0.0439 (6)
H1261.57010.71650.18170.053*
N1271.59827 (15)0.76199 (14)0.25778 (7)0.0397 (5)
C1281.5648 (3)0.7395 (2)0.30642 (10)0.0647 (8)
H12G1.51940.77080.31930.097*
H12H1.62970.76170.33250.097*
H12I1.52270.67060.30060.097*
C1291.6664 (2)0.86026 (18)0.25941 (12)0.0608 (8)
H12J1.68170.86660.22390.091*
H12K1.73530.88250.28260.091*
H12L1.62840.89850.27280.091*
O1301.04601 (15)0.46155 (13)0.43644 (9)0.0664 (6)
C1311.0999 (2)0.50711 (17)0.42820 (11)0.0458 (6)
H1311.16210.48930.45330.055*
N1321.07794 (15)0.57862 (13)0.38727 (8)0.0369 (5)
C1331.1410 (2)0.63312 (17)0.38350 (11)0.0457 (6)
H13A1.19960.60530.41360.069*
H13B1.17300.63180.35080.069*
H13C1.09300.69890.38360.069*
C1340.9868 (2)0.60799 (19)0.34651 (11)0.0530 (7)
H13D0.92320.66120.35320.079*
H13E1.00670.62780.31220.079*
H13F0.96890.55480.34650.079*
O1350.61712 (17)0.60059 (13)0.69760 (7)0.0610 (5)
C1360.6591 (2)0.68716 (19)0.71438 (10)0.0441 (6)
H1360.72330.72300.70100.053*
N1370.62302 (15)0.73484 (13)0.74933 (8)0.0390 (5)
C1380.6754 (2)0.83740 (18)0.76594 (11)0.0505 (7)
H13G0.74090.86240.74910.076*
H13H0.69600.85740.80420.076*
H13I0.62460.86190.75580.076*
C1390.5257 (3)0.6852 (2)0.77182 (15)0.0878 (12)
H13J0.47320.71090.76680.132*
H13K0.54560.69390.80950.132*
H13L0.49250.61740.75430.132*
O40A0.2034 (4)0.3981 (3)0.75012 (18)0.0729 (12)0.50
C41A0.2395 (5)0.4579 (4)0.7354 (3)0.0613 (16)0.50
H41A0.24600.45830.69950.074*0.50
N42A0.2709 (4)0.5165 (4)0.7436 (2)0.0734 (15)0.50
C43A0.3029 (6)0.5096 (5)0.8044 (3)0.081 (2)0.50
H4AA0.29610.45560.82640.122*0.50
H4BA0.37840.50090.81050.122*0.50
H4CA0.25360.56830.81330.122*0.50
C44A0.2756 (5)0.5958 (4)0.7091 (3)0.0707 (18)0.50
H4DA0.24820.60070.67290.106*0.50
H4EA0.23030.65410.71950.106*0.50
H4FA0.35150.58690.71110.106*0.50
O40B0.2392 (4)0.3898 (3)0.76925 (19)0.0637 (13)0.50
C41B0.2391 (6)0.4428 (6)0.7735 (3)0.075 (2)0.50
H41B0.21130.45400.80530.091*0.50
N42B0.2642 (3)0.5166 (3)0.75133 (16)0.0431 (10)0.50
C43B0.3041 (6)0.5623 (5)0.7771 (3)0.087 (2)0.50
H4AB0.37600.55300.76740.130*0.50
H4BB0.25420.63030.76770.130*0.50
H4CB0.31140.53710.81510.130*0.50
C44B0.2465 (7)0.5428 (6)0.6908 (3)0.096 (2)0.50
H4DB0.31740.52580.67820.144*0.50
H4EB0.21020.50800.67800.144*0.50
H4FB0.20060.61120.67780.144*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0269 (12)0.0301 (13)0.0325 (13)0.0110 (10)0.0062 (10)0.0095 (10)
C20.0267 (12)0.0353 (14)0.0356 (13)0.0110 (10)0.0087 (10)0.0126 (10)
C30.0303 (12)0.0328 (13)0.0317 (13)0.0140 (10)0.0082 (10)0.0133 (10)
C40.0315 (12)0.0293 (13)0.0271 (12)0.0148 (10)0.0055 (10)0.0079 (9)
C50.0288 (12)0.0294 (13)0.0235 (11)0.0148 (10)0.0037 (9)0.0028 (9)
C60.0281 (12)0.0256 (12)0.0224 (11)0.0128 (9)0.0040 (9)0.0021 (9)
C70.0295 (12)0.0319 (13)0.0283 (12)0.0167 (10)0.0031 (10)0.0069 (10)
C80.0263 (12)0.0298 (13)0.0320 (12)0.0127 (10)0.0038 (10)0.0045 (10)
C90.0239 (11)0.0306 (13)0.0237 (11)0.0136 (10)0.0055 (9)0.0023 (9)
C100.0267 (12)0.0258 (12)0.0245 (11)0.0112 (9)0.0065 (9)0.0030 (9)
C110.0258 (11)0.0251 (12)0.0233 (11)0.0097 (9)0.0055 (9)0.0012 (9)
C120.0326 (13)0.0249 (13)0.0341 (13)0.0099 (10)0.0044 (10)0.0071 (10)
C130.0347 (13)0.0286 (13)0.0344 (13)0.0147 (10)0.0025 (10)0.0094 (10)
C140.0286 (12)0.0294 (13)0.0274 (12)0.0139 (10)0.0051 (10)0.0074 (9)
C150.0292 (12)0.0301 (13)0.0236 (11)0.0155 (10)0.0034 (9)0.0056 (9)
C160.0257 (11)0.0324 (13)0.0260 (12)0.0162 (10)0.0043 (9)0.0061 (9)
C170.0292 (12)0.0345 (14)0.0268 (12)0.0161 (10)0.0023 (10)0.0047 (10)
C180.0259 (12)0.0305 (13)0.0320 (13)0.0105 (10)0.0019 (10)0.0077 (10)
C190.0242 (11)0.0292 (13)0.0300 (12)0.0119 (10)0.0051 (9)0.0054 (9)
C200.0246 (11)0.0293 (13)0.0317 (12)0.0119 (10)0.0062 (10)0.0074 (9)
N210.0233 (9)0.0300 (10)0.0281 (10)0.0098 (8)0.0021 (8)0.0075 (8)
N220.0226 (9)0.0291 (10)0.0239 (9)0.0115 (8)0.0026 (7)0.0042 (8)
N230.0266 (10)0.0284 (10)0.0242 (10)0.0109 (8)0.0022 (8)0.0058 (8)
N240.0245 (10)0.0309 (11)0.0257 (10)0.0104 (8)0.0007 (8)0.0065 (8)
C250.0237 (11)0.0278 (12)0.0277 (12)0.0104 (9)0.0024 (9)0.0083 (9)
C260.0254 (11)0.0304 (13)0.0247 (12)0.0113 (10)0.0033 (9)0.0033 (9)
C270.0292 (12)0.0250 (12)0.0346 (13)0.0129 (10)0.0046 (10)0.0068 (10)
C280.0316 (13)0.0375 (14)0.0275 (13)0.0149 (10)0.0013 (10)0.0110 (10)
C290.0433 (14)0.0354 (14)0.0252 (12)0.0187 (11)0.0004 (10)0.0014 (10)
C300.0383 (13)0.0295 (13)0.0311 (13)0.0176 (11)0.0015 (10)0.0036 (10)
O310.0606 (11)0.0447 (11)0.0338 (9)0.0286 (10)0.0027 (8)0.0110 (8)
C320.0249 (11)0.0275 (12)0.0316 (12)0.0137 (9)0.0052 (9)0.0052 (9)
C330.0299 (12)0.0310 (13)0.0268 (12)0.0119 (10)0.0046 (10)0.0043 (9)
C340.0344 (13)0.0361 (14)0.0274 (12)0.0158 (11)0.0002 (10)0.0022 (10)
C350.0247 (12)0.0278 (13)0.0434 (14)0.0095 (10)0.0030 (10)0.0037 (10)
C360.0283 (12)0.0315 (13)0.0380 (14)0.0131 (10)0.0079 (10)0.0100 (10)
C370.0300 (12)0.0291 (13)0.0289 (12)0.0138 (10)0.0048 (10)0.0058 (9)
O380.0317 (9)0.0330 (10)0.0477 (10)0.0048 (7)0.0014 (8)0.0012 (8)
C390.0288 (12)0.0235 (12)0.0289 (12)0.0084 (9)0.0017 (10)0.0031 (9)
C400.0298 (12)0.0316 (13)0.0340 (13)0.0141 (10)0.0006 (10)0.0084 (10)
C410.0323 (13)0.0326 (13)0.0308 (13)0.0127 (10)0.0019 (10)0.0094 (10)
C420.0349 (13)0.0269 (13)0.0293 (13)0.0121 (10)0.0021 (10)0.0077 (10)
C430.0291 (12)0.0335 (13)0.0395 (14)0.0167 (10)0.0002 (11)0.0076 (10)
C440.0280 (12)0.0316 (13)0.0353 (13)0.0119 (10)0.0044 (10)0.0072 (10)
O450.0400 (10)0.0457 (10)0.0392 (10)0.0230 (8)0.0034 (8)0.0168 (8)
C460.0246 (12)0.0311 (13)0.0311 (12)0.0085 (10)0.0030 (9)0.0106 (10)
C470.0303 (13)0.0330 (14)0.0424 (14)0.0136 (11)0.0028 (11)0.0089 (11)
C480.0240 (12)0.0375 (15)0.0506 (15)0.0122 (11)0.0027 (11)0.0086 (11)
C490.0284 (13)0.0328 (14)0.0391 (14)0.0052 (11)0.0025 (10)0.0054 (10)
C500.0334 (13)0.0297 (14)0.0442 (14)0.0122 (11)0.0047 (11)0.0022 (10)
C510.0294 (13)0.0341 (14)0.0403 (14)0.0147 (11)0.0043 (10)0.0087 (11)
O520.0303 (9)0.0372 (10)0.0682 (12)0.0105 (8)0.0016 (9)0.0008 (9)
C530.0303 (12)0.0238 (12)0.0326 (12)0.0152 (10)0.0083 (10)0.0079 (9)
C540.0315 (12)0.0323 (13)0.0338 (13)0.0188 (10)0.0085 (10)0.0111 (10)
C550.0314 (12)0.0300 (13)0.0292 (12)0.0141 (10)0.0088 (10)0.0118 (9)
C560.0289 (12)0.0253 (12)0.0237 (11)0.0117 (9)0.0059 (9)0.0051 (9)
C570.0269 (11)0.0264 (12)0.0225 (11)0.0120 (9)0.0037 (9)0.0026 (9)
C580.0247 (11)0.0230 (12)0.0232 (11)0.0099 (9)0.0030 (9)0.0019 (9)
C590.0239 (11)0.0268 (12)0.0284 (12)0.0100 (9)0.0054 (9)0.0027 (9)
C600.0275 (12)0.0272 (12)0.0266 (12)0.0152 (9)0.0040 (9)0.0026 (9)
C610.0242 (11)0.0235 (12)0.0236 (11)0.0108 (9)0.0020 (9)0.0016 (9)
C620.0255 (11)0.0237 (12)0.0234 (11)0.0116 (9)0.0013 (9)0.0020 (9)
C630.0253 (11)0.0230 (12)0.0239 (11)0.0109 (9)0.0010 (9)0.0041 (9)
C640.0308 (12)0.0238 (12)0.0288 (12)0.0129 (10)0.0040 (10)0.0052 (9)
C650.0285 (12)0.0256 (12)0.0285 (12)0.0117 (10)0.0057 (9)0.0070 (9)
C660.0253 (11)0.0265 (12)0.0246 (11)0.0125 (9)0.0040 (9)0.0076 (9)
C670.0235 (11)0.0259 (12)0.0258 (11)0.0124 (9)0.0027 (9)0.0053 (9)
C680.0264 (11)0.0298 (13)0.0243 (11)0.0143 (10)0.0044 (9)0.0062 (9)
C690.0305 (12)0.0325 (13)0.0271 (12)0.0168 (10)0.0098 (10)0.0075 (10)
C700.0331 (12)0.0272 (13)0.0325 (12)0.0171 (10)0.0086 (10)0.0056 (10)
C710.0222 (11)0.0273 (12)0.0312 (12)0.0132 (9)0.0061 (9)0.0051 (9)
C720.0248 (11)0.0256 (12)0.0317 (12)0.0129 (9)0.0065 (9)0.0074 (9)
N730.0286 (10)0.0266 (10)0.0297 (10)0.0148 (8)0.0089 (8)0.0088 (8)
N740.0252 (9)0.0250 (10)0.0262 (9)0.0137 (8)0.0065 (8)0.0051 (7)
N750.0269 (10)0.0259 (10)0.0250 (9)0.0146 (8)0.0060 (8)0.0049 (7)
N760.0276 (10)0.0275 (10)0.0272 (10)0.0167 (8)0.0087 (8)0.0064 (8)
C770.0269 (11)0.0271 (12)0.0264 (12)0.0148 (10)0.0044 (9)0.0047 (9)
C780.0288 (12)0.0309 (13)0.0289 (12)0.0153 (10)0.0052 (10)0.0057 (9)
C790.0305 (12)0.0322 (13)0.0382 (13)0.0154 (10)0.0114 (10)0.0126 (10)
C800.0408 (14)0.0426 (15)0.0325 (13)0.0247 (12)0.0175 (11)0.0158 (11)
C810.0459 (15)0.0352 (14)0.0296 (13)0.0222 (12)0.0075 (11)0.0039 (10)
C820.0359 (13)0.0294 (13)0.0294 (12)0.0151 (10)0.0067 (10)0.0064 (10)
O830.0653 (13)0.0501 (11)0.0448 (10)0.0278 (10)0.0330 (9)0.0210 (9)
C840.0245 (11)0.0235 (12)0.0267 (12)0.0105 (9)0.0049 (9)0.0062 (9)
C850.0322 (12)0.0276 (13)0.0272 (12)0.0138 (10)0.0053 (10)0.0083 (9)
C860.0353 (13)0.0267 (13)0.0288 (12)0.0152 (10)0.0069 (10)0.0021 (9)
C870.0256 (12)0.0235 (12)0.0433 (14)0.0137 (9)0.0101 (10)0.0079 (10)
C880.0299 (12)0.0305 (13)0.0333 (13)0.0162 (10)0.0064 (10)0.0101 (10)
C890.0275 (12)0.0277 (12)0.0279 (12)0.0125 (10)0.0062 (9)0.0038 (9)
O900.0423 (10)0.0272 (9)0.0472 (10)0.0213 (8)0.0076 (8)0.0057 (7)
C910.0297 (12)0.0225 (12)0.0268 (12)0.0116 (9)0.0074 (9)0.0041 (9)
C920.0284 (12)0.0264 (12)0.0296 (12)0.0151 (10)0.0078 (10)0.0048 (9)
C930.0350 (13)0.0289 (13)0.0264 (12)0.0164 (10)0.0062 (10)0.0084 (9)
C940.0322 (13)0.0241 (12)0.0287 (12)0.0106 (10)0.0114 (10)0.0055 (9)
C950.0290 (12)0.0277 (13)0.0333 (13)0.0142 (10)0.0091 (10)0.0061 (10)
C960.0303 (12)0.0261 (12)0.0291 (12)0.0143 (10)0.0050 (10)0.0066 (9)
O970.0377 (9)0.0473 (10)0.0342 (9)0.0215 (8)0.0139 (8)0.0160 (8)
C980.0328 (13)0.0297 (13)0.0299 (12)0.0180 (10)0.0117 (10)0.0112 (10)
C990.0329 (13)0.0299 (13)0.0361 (13)0.0171 (10)0.0040 (10)0.0071 (10)
C1000.0316 (13)0.0359 (14)0.0453 (14)0.0218 (11)0.0073 (11)0.0080 (11)
C1010.0391 (14)0.0280 (13)0.0463 (14)0.0214 (11)0.0166 (11)0.0098 (11)
C1020.0330 (13)0.0279 (13)0.0514 (15)0.0117 (11)0.0104 (11)0.0053 (11)
C1030.0288 (13)0.0343 (14)0.0494 (15)0.0164 (11)0.0124 (11)0.0116 (11)
O1040.0421 (10)0.0319 (10)0.0823 (13)0.0224 (8)0.0112 (10)0.0025 (9)
O1050.0434 (10)0.0506 (11)0.0343 (9)0.0247 (9)0.0133 (8)0.0164 (8)
C1060.0425 (15)0.0506 (17)0.0343 (14)0.0281 (13)0.0146 (12)0.0133 (12)
N1070.0437 (12)0.0515 (14)0.0372 (12)0.0301 (11)0.0134 (10)0.0087 (10)
C1080.0447 (16)0.0599 (19)0.0656 (19)0.0282 (15)0.0029 (14)0.0026 (15)
C1090.0614 (18)0.073 (2)0.0471 (16)0.0446 (16)0.0146 (14)0.0234 (14)
O1100.0446 (10)0.0468 (11)0.0371 (9)0.0234 (9)0.0036 (8)0.0140 (8)
C1110.0293 (13)0.0497 (16)0.0338 (14)0.0147 (12)0.0032 (11)0.0117 (12)
N1120.0309 (11)0.0595 (15)0.0325 (11)0.0176 (10)0.0020 (9)0.0072 (10)
C1130.0477 (17)0.096 (2)0.0465 (17)0.0433 (17)0.0004 (13)0.0022 (16)
C1140.0411 (16)0.077 (2)0.0421 (16)0.0106 (15)0.0039 (13)0.0257 (14)
O1150.0481 (11)0.0442 (11)0.0779 (14)0.0225 (9)0.0002 (10)0.0116 (9)
C1160.0528 (17)0.0493 (17)0.0443 (16)0.0273 (14)0.0026 (13)0.0079 (13)
N1170.0721 (16)0.0647 (17)0.0457 (14)0.0456 (14)0.0049 (12)0.0092 (12)
C1180.088 (2)0.0449 (19)0.080 (2)0.0328 (17)0.0176 (19)0.0098 (16)
C1190.135 (4)0.196 (5)0.103 (3)0.139 (4)0.040 (3)0.042 (3)
O1200.0342 (11)0.0455 (11)0.0724 (13)0.0118 (9)0.0047 (9)0.0058 (9)
C1210.0360 (15)0.0345 (15)0.0522 (16)0.0119 (12)0.0049 (12)0.0006 (12)
N1220.0385 (12)0.0327 (12)0.0443 (12)0.0135 (9)0.0011 (10)0.0036 (9)
C1230.072 (2)0.0462 (17)0.0430 (16)0.0221 (15)0.0093 (14)0.0071 (13)
C1240.0359 (15)0.0440 (17)0.0691 (19)0.0081 (12)0.0040 (13)0.0063 (14)
O1250.0561 (12)0.0396 (12)0.0542 (12)0.0088 (9)0.0004 (9)0.0004 (9)
C1260.0435 (15)0.0495 (18)0.0361 (15)0.0197 (13)0.0051 (12)0.0068 (12)
N1270.0335 (11)0.0445 (13)0.0334 (12)0.0141 (10)0.0036 (9)0.0006 (9)
C1280.072 (2)0.077 (2)0.0364 (16)0.0297 (17)0.0057 (15)0.0022 (14)
C1290.0459 (17)0.0396 (17)0.080 (2)0.0110 (13)0.0107 (15)0.0009 (14)
O1300.0454 (11)0.0466 (12)0.1014 (16)0.0298 (10)0.0019 (11)0.0136 (11)
C1310.0359 (14)0.0349 (15)0.0630 (18)0.0182 (12)0.0026 (13)0.0004 (13)
N1320.0303 (11)0.0310 (11)0.0476 (12)0.0153 (9)0.0047 (9)0.0018 (9)
C1330.0417 (15)0.0355 (15)0.0630 (17)0.0223 (12)0.0138 (13)0.0051 (12)
C1340.0481 (16)0.0523 (18)0.0563 (18)0.0218 (14)0.0006 (14)0.0107 (14)
O1350.0863 (15)0.0365 (12)0.0564 (12)0.0262 (10)0.0227 (11)0.0024 (9)
C1360.0509 (16)0.0409 (17)0.0447 (15)0.0245 (13)0.0174 (13)0.0074 (12)
N1370.0356 (11)0.0362 (12)0.0413 (12)0.0156 (9)0.0091 (9)0.0010 (9)
C1380.0460 (16)0.0444 (17)0.0556 (17)0.0213 (13)0.0096 (13)0.0030 (13)
C1390.072 (2)0.058 (2)0.111 (3)0.0122 (18)0.050 (2)0.0015 (19)
O40A0.082 (3)0.065 (3)0.098 (3)0.042 (2)0.044 (3)0.048 (2)
C41A0.055 (4)0.043 (4)0.097 (5)0.022 (3)0.044 (3)0.033 (3)
N42A0.076 (4)0.076 (4)0.096 (4)0.048 (3)0.042 (3)0.041 (3)
C43A0.075 (5)0.084 (5)0.096 (4)0.028 (4)0.036 (4)0.054 (4)
C44A0.074 (4)0.064 (4)0.093 (5)0.043 (4)0.027 (4)0.030 (3)
O40B0.073 (3)0.050 (3)0.090 (3)0.032 (3)0.040 (2)0.046 (3)
C41B0.062 (4)0.068 (5)0.115 (6)0.029 (4)0.054 (4)0.051 (4)
N42B0.038 (2)0.037 (2)0.043 (2)0.0019 (19)0.0128 (19)0.0167 (19)
C43B0.067 (4)0.097 (5)0.127 (6)0.042 (4)0.031 (4)0.075 (5)
C44B0.114 (6)0.106 (6)0.064 (4)0.047 (5)0.011 (4)0.015 (4)
Geometric parameters (Å, º) top
C1—N211.386 (3)C80—O831.372 (3)
C1—C201.398 (3)C80—C811.376 (3)
C1—C21.427 (3)C81—C821.383 (3)
C2—C31.363 (3)C81—H810.9500
C2—H20.9500C82—H820.9500
C3—C41.427 (3)O83—H830.8400
C3—H30.9500C84—C891.394 (3)
C4—N211.378 (3)C84—C851.397 (3)
C4—C51.409 (3)C85—C861.391 (3)
C5—C61.408 (3)C85—H850.9500
C5—C251.497 (3)C86—C871.387 (3)
C6—N221.362 (3)C86—H860.9500
C6—C71.452 (3)C87—O901.367 (2)
C7—C81.344 (3)C87—C881.391 (3)
C7—H70.9500C88—C891.384 (3)
C8—C91.455 (3)C88—H880.9500
C8—H80.9500C89—H890.9500
C9—N221.372 (3)O90—H900.8400
C9—C101.408 (3)C91—C921.399 (3)
C10—C111.406 (3)C91—C961.401 (3)
C10—C321.493 (3)C92—C931.381 (3)
C11—N231.382 (3)C92—H920.9500
C11—C121.416 (3)C93—C941.385 (3)
C12—C131.361 (3)C93—H930.9500
C12—H120.9500C94—O971.368 (2)
C13—C141.420 (3)C94—C951.395 (3)
C13—H130.9500C95—C961.380 (3)
C14—N231.378 (3)C95—H950.9500
C14—C151.409 (3)C96—H960.9500
C15—C161.402 (3)O97—H970.8400
C15—C391.495 (3)C98—C991.385 (3)
C16—N241.362 (3)C98—C1031.395 (3)
C16—C171.453 (3)C99—C1001.387 (3)
C17—C181.332 (3)C99—H990.9500
C17—H170.9500C100—C1011.389 (3)
C18—C191.450 (3)C100—H1000.9500
C18—H180.9500C101—O1041.363 (3)
C19—N241.362 (3)C101—C1021.382 (3)
C19—C201.413 (3)C102—C1031.382 (3)
C20—C461.495 (3)C102—H1020.9500
N21—H210.8800C103—H1030.9500
N22—H220.8800O104—H1040.8400
N23—H230.8800O105—C1061.241 (3)
N24—H240.8800C106—N1071.326 (3)
C25—C301.393 (3)C106—H1060.9500
C25—C261.396 (3)N107—C1091.446 (3)
C26—C271.383 (3)N107—C1081.452 (3)
C26—H260.9500C108—H10A0.9800
C27—C281.393 (3)C108—H10B0.9800
C27—H270.9500C108—H10C0.9800
C28—O311.365 (3)C109—H10D0.9800
C28—C291.386 (3)C109—H10E0.9800
C29—C301.381 (3)C109—H10F0.9800
C29—H290.9500O110—C1111.244 (3)
C30—H300.9500C111—N1121.314 (3)
O31—H310.8400C111—H1110.9500
C32—C331.394 (3)N112—C1141.446 (3)
C32—C371.399 (3)N112—C1131.450 (3)
C33—C341.388 (3)C113—H11A0.9800
C33—H330.9500C113—H11B0.9800
C34—C351.389 (3)C113—H11C0.9800
C34—H340.9500C114—H11D0.9800
C35—O381.364 (3)C114—H11E0.9800
C35—C361.386 (3)C114—H11F0.9800
C36—C371.383 (3)O115—C1161.216 (3)
C36—H360.9500C116—N1171.308 (3)
C37—H370.9500C116—H1160.9500
O38—H380.8400N117—C1181.477 (5)
C39—C441.391 (3)N117—C1191.478 (5)
C39—C401.400 (3)C118—H11G0.9800
C40—C411.378 (3)C118—H11H0.9800
C40—H400.9500C118—H11I0.9800
C41—C421.398 (3)C119—H11J0.9800
C41—H410.9500C119—H11K0.9800
C42—O451.355 (3)C119—H11L0.9800
C42—C431.386 (3)O120—C1211.229 (3)
C43—C441.389 (3)C121—N1221.315 (3)
C43—H430.9500C121—H1210.9500
C44—H440.9500N122—C1231.445 (3)
O45—H450.8400N122—C1241.449 (3)
C46—C471.391 (3)C123—H12A0.9800
C46—C511.395 (3)C123—H12B0.9800
C47—C481.390 (3)C123—H12C0.9800
C47—H470.9500C124—H12D0.9800
C48—C491.392 (3)C124—H12E0.9800
C48—H480.9500C124—H12F0.9800
C49—O521.371 (3)O125—C1261.240 (3)
C49—C501.377 (3)C126—N1271.313 (3)
C50—C511.389 (3)C126—H1260.9500
C50—H500.9500N127—C1281.438 (3)
C51—H510.9500N127—C1291.442 (3)
O52—H520.8400C128—H12G0.9800
C53—N731.381 (3)C128—H12H0.9800
C53—C721.397 (3)C128—H12I0.9800
C53—C541.424 (3)C129—H12J0.9800
C54—C551.365 (3)C129—H12K0.9800
C54—H540.9500C129—H12L0.9800
C55—C561.435 (3)O130—C1311.233 (3)
C55—H550.9500C131—N1321.318 (3)
C56—N731.376 (3)C131—H1310.9500
C56—C571.405 (3)N132—C1341.447 (3)
C57—C581.405 (3)N132—C1331.454 (3)
C57—C771.496 (3)C133—H13A0.9800
C58—N741.369 (3)C133—H13B0.9800
C58—C591.457 (3)C133—H13C0.9800
C59—C601.339 (3)C134—H13D0.9800
C59—H590.9500C134—H13E0.9800
C60—C611.454 (3)C134—H13F0.9800
C60—H600.9500O135—C1361.227 (3)
C61—N741.367 (3)C136—N1371.318 (3)
C61—C621.410 (3)C136—H1360.9500
C62—C631.403 (3)N137—C1381.446 (3)
C62—C841.492 (3)N137—C1391.453 (3)
C63—N751.374 (3)C138—H13G0.9800
C63—C641.428 (3)C138—H13H0.9800
C64—C651.361 (3)C138—H13I0.9800
C64—H640.9500C139—H13J0.9800
C65—C661.423 (3)C139—H13K0.9800
C65—H650.9500C139—H13L0.9800
C66—N751.382 (3)O40A—C41A1.253 (7)
C66—C671.402 (3)C41A—N42A1.234 (7)
C67—C681.403 (3)C41A—H41A0.9500
C67—C911.491 (3)N42A—C44A1.429 (8)
C68—N761.369 (3)N42A—C43A1.605 (9)
C68—C691.458 (3)C43A—H4AA0.9800
C69—C701.337 (3)C43A—H4BA0.9800
C69—H690.9500C43A—H4CA0.9800
C70—C711.456 (3)C44A—H4DA0.9800
C70—H700.9500C44A—H4EA0.9800
C71—N761.364 (3)C44A—H4FA0.9800
C71—C721.411 (3)O40B—C41B0.878 (7)
C72—C981.497 (3)C41B—N42B1.389 (9)
N73—H730.8800C41B—H41B0.9500
N74—H740.8800N42B—C43B1.340 (7)
N75—H750.8800N42B—C44B1.538 (8)
N76—H760.8800C43B—H4AB0.9800
C77—C781.392 (3)C43B—H4BB0.9800
C77—C821.401 (3)C43B—H4CB0.9800
C78—C791.390 (3)C44B—H4DB0.9800
C78—H780.9500C44B—H4EB0.9800
C79—C801.383 (3)C44B—H4FB0.9800
C79—H790.9500
N21—C1—C20125.64 (19)C79—C78—C77121.6 (2)
N21—C1—C2106.53 (19)C79—C78—H78119.2
C20—C1—C2127.8 (2)C77—C78—H78119.2
C3—C2—C1108.18 (19)C80—C79—C78119.9 (2)
C3—C2—H2125.9C80—C79—H79120.1
C1—C2—H2125.9C78—C79—H79120.1
C2—C3—C4108.7 (2)O83—C80—C81117.9 (2)
C2—C3—H3125.7O83—C80—C79122.5 (2)
C4—C3—H3125.7C81—C80—C79119.6 (2)
N21—C4—C5126.60 (19)C80—C81—C82120.5 (2)
N21—C4—C3106.45 (18)C80—C81—H81119.8
C5—C4—C3126.9 (2)C82—C81—H81119.8
C6—C5—C4125.3 (2)C81—C82—C77121.2 (2)
C6—C5—C25118.72 (18)C81—C82—H82119.4
C4—C5—C25115.94 (19)C77—C82—H82119.4
N22—C6—C5126.13 (19)C80—O83—H83109.5
N22—C6—C7110.63 (18)C89—C84—C85117.46 (19)
C5—C6—C7123.21 (19)C89—C84—C62122.33 (18)
C8—C7—C6106.74 (19)C85—C84—C62120.21 (18)
C8—C7—H7126.6C86—C85—C84121.1 (2)
C6—C7—H7126.6C86—C85—H85119.5
C7—C8—C9106.58 (19)C84—C85—H85119.5
C7—C8—H8126.7C87—C86—C85120.4 (2)
C9—C8—H8126.7C87—C86—H86119.8
N22—C9—C10125.90 (19)C85—C86—H86119.8
N22—C9—C8110.27 (18)O90—C87—C86122.70 (19)
C10—C9—C8123.76 (19)O90—C87—C88117.99 (19)
C11—C10—C9123.66 (19)C86—C87—C88119.30 (19)
C11—C10—C32117.51 (18)C89—C88—C87119.8 (2)
C9—C10—C32118.82 (19)C89—C88—H88120.1
N23—C11—C10125.21 (19)C87—C88—H88120.1
N23—C11—C12106.73 (18)C88—C89—C84121.95 (19)
C10—C11—C12128.05 (19)C88—C89—H89119.0
C13—C12—C11108.48 (19)C84—C89—H89119.0
C13—C12—H12125.8C87—O90—H90109.5
C11—C12—H12125.8C92—C91—C96117.76 (19)
C12—C13—C14108.3 (2)C92—C91—C67120.77 (18)
C12—C13—H13125.9C96—C91—C67121.43 (19)
C14—C13—H13125.9C93—C92—C91121.6 (2)
N23—C14—C15126.49 (19)C93—C92—H92119.2
N23—C14—C13106.83 (18)C91—C92—H92119.2
C15—C14—C13126.7 (2)C92—C93—C94120.0 (2)
C16—C15—C14125.20 (19)C92—C93—H93120.0
C16—C15—C39118.66 (18)C94—C93—H93120.0
C14—C15—C39116.14 (18)O97—C94—C93123.0 (2)
N24—C16—C15125.78 (19)O97—C94—C95117.71 (19)
N24—C16—C17110.39 (18)C93—C94—C95119.31 (19)
C15—C16—C17123.78 (19)C96—C95—C94120.6 (2)
C18—C17—C16106.81 (19)C96—C95—H95119.7
C18—C17—H17126.6C94—C95—H95119.7
C16—C17—H17126.6C95—C96—C91120.8 (2)
C17—C18—C19106.62 (19)C95—C96—H96119.6
C17—C18—H18126.7C91—C96—H96119.6
C19—C18—H18126.7C94—O97—H97109.5
N24—C19—C20125.90 (19)C99—C98—C103117.73 (19)
N24—C19—C18110.68 (18)C99—C98—C72121.81 (19)
C20—C19—C18123.42 (19)C103—C98—C72120.06 (19)
C1—C20—C19124.18 (19)C98—C99—C100121.5 (2)
C1—C20—C46118.54 (19)C98—C99—H99119.2
C19—C20—C46117.28 (19)C100—C99—H99119.2
C4—N21—C1110.14 (17)C99—C100—C101119.6 (2)
C4—N21—H21124.9C99—C100—H100120.2
C1—N21—H21124.9C101—C100—H100120.2
C6—N22—C9105.65 (16)O104—C101—C102118.1 (2)
C6—N22—H22127.2O104—C101—C100122.2 (2)
C9—N22—H22127.2C102—C101—C100119.7 (2)
C14—N23—C11109.62 (17)C101—C102—C103120.0 (2)
C14—N23—H23125.2C101—C102—H102120.0
C11—N23—H23125.2C103—C102—H102120.0
C19—N24—C16105.46 (17)C102—C103—C98121.4 (2)
C19—N24—H24127.3C102—C103—H103119.3
C16—N24—H24127.3C98—C103—H103119.3
C30—C25—C26118.01 (19)C101—O104—H104109.5
C30—C25—C5120.48 (19)O105—C106—N107125.1 (2)
C26—C25—C5121.48 (18)O105—C106—H106117.4
C27—C26—C25121.14 (19)N107—C106—H106117.4
C27—C26—H26119.4C106—N107—C109120.8 (2)
C25—C26—H26119.4C106—N107—C108121.6 (2)
C26—C27—C28119.9 (2)C109—N107—C108117.4 (2)
C26—C27—H27120.1N107—C108—H10A109.5
C28—C27—H27120.1N107—C108—H10B109.5
O31—C28—C29117.71 (19)H10A—C108—H10B109.5
O31—C28—C27122.7 (2)N107—C108—H10C109.5
C29—C28—C27119.6 (2)H10A—C108—H10C109.5
C30—C29—C28120.1 (2)H10B—C108—H10C109.5
C30—C29—H29120.0N107—C109—H10D109.5
C28—C29—H29120.0N107—C109—H10E109.5
C29—C30—C25121.3 (2)H10D—C109—H10E109.5
C29—C30—H30119.4N107—C109—H10F109.5
C25—C30—H30119.4H10D—C109—H10F109.5
C28—O31—H31109.5H10E—C109—H10F109.5
C33—C32—C37117.59 (19)O110—C111—N112125.7 (2)
C33—C32—C10121.38 (19)O110—C111—H111117.1
C37—C32—C10121.03 (19)N112—C111—H111117.1
C34—C33—C32121.1 (2)C111—N112—C114121.3 (2)
C34—C33—H33119.4C111—N112—C113120.7 (2)
C32—C33—H33119.4C114—N112—C113117.8 (2)
C33—C34—C35120.2 (2)N112—C113—H11A109.5
C33—C34—H34119.9N112—C113—H11B109.5
C35—C34—H34119.9H11A—C113—H11B109.5
O38—C35—C36117.4 (2)N112—C113—H11C109.5
O38—C35—C34123.1 (2)H11A—C113—H11C109.5
C36—C35—C34119.4 (2)H11B—C113—H11C109.5
C37—C36—C35120.0 (2)N112—C114—H11D109.5
C37—C36—H36120.0N112—C114—H11E109.5
C35—C36—H36120.0H11D—C114—H11E109.5
C36—C37—C32121.6 (2)N112—C114—H11F109.5
C36—C37—H37119.2H11D—C114—H11F109.5
C32—C37—H37119.2H11E—C114—H11F109.5
C35—O38—H38109.5O115—C116—N117125.8 (3)
C44—C39—C40117.7 (2)O115—C116—H116117.1
C44—C39—C15121.6 (2)N117—C116—H116117.1
C40—C39—C15120.69 (19)C116—N117—C118121.3 (2)
C41—C40—C39121.6 (2)C116—N117—C119121.0 (2)
C41—C40—H40119.2C118—N117—C119117.2 (3)
C39—C40—H40119.2N117—C118—H11G109.5
C40—C41—C42120.1 (2)N117—C118—H11H109.5
C40—C41—H41120.0H11G—C118—H11H109.5
C42—C41—H41120.0N117—C118—H11I109.5
O45—C42—C43117.9 (2)H11G—C118—H11I109.5
O45—C42—C41123.0 (2)H11H—C118—H11I109.5
C43—C42—C41119.1 (2)N117—C119—H11J109.5
C42—C43—C44120.4 (2)N117—C119—H11K109.5
C42—C43—H43119.8H11J—C119—H11K109.5
C44—C43—H43119.8N117—C119—H11L109.5
C43—C44—C39121.2 (2)H11J—C119—H11L109.5
C43—C44—H44119.4H11K—C119—H11L109.5
C39—C44—H44119.4O120—C121—N122126.4 (2)
C42—O45—H45109.5O120—C121—H121116.8
C47—C46—C51117.9 (2)N122—C121—H121116.8
C47—C46—C20120.8 (2)C121—N122—C123120.7 (2)
C51—C46—C20121.2 (2)C121—N122—C124121.8 (2)
C48—C47—C46121.3 (2)C123—N122—C124117.4 (2)
C48—C47—H47119.3N122—C123—H12A109.5
C46—C47—H47119.3N122—C123—H12B109.5
C47—C48—C49119.6 (2)H12A—C123—H12B109.5
C47—C48—H48120.2N122—C123—H12C109.5
C49—C48—H48120.2H12A—C123—H12C109.5
O52—C49—C50117.8 (2)H12B—C123—H12C109.5
O52—C49—C48122.3 (2)N122—C124—H12D109.5
C50—C49—C48119.9 (2)N122—C124—H12E109.5
C49—C50—C51120.1 (2)H12D—C124—H12E109.5
C49—C50—H50119.9N122—C124—H12F109.5
C51—C50—H50119.9H12D—C124—H12F109.5
C50—C51—C46121.1 (2)H12E—C124—H12F109.5
C50—C51—H51119.4O125—C126—N127125.4 (2)
C46—C51—H51119.4O125—C126—H126117.3
C49—O52—H52109.5N127—C126—H126117.3
N73—C53—C72125.72 (19)C126—N127—C128119.5 (2)
N73—C53—C54106.64 (18)C126—N127—C129122.3 (2)
C72—C53—C54127.61 (19)C128—N127—C129117.2 (2)
C55—C54—C53108.24 (19)N127—C128—H12G109.5
C55—C54—H54125.9N127—C128—H12H109.5
C53—C54—H54125.9H12G—C128—H12H109.5
C54—C55—C56108.48 (19)N127—C128—H12I109.5
C54—C55—H55125.8H12G—C128—H12I109.5
C56—C55—H55125.8H12H—C128—H12I109.5
N73—C56—C57125.92 (19)N127—C129—H12J109.5
N73—C56—C55106.13 (17)N127—C129—H12K109.5
C57—C56—C55127.85 (19)H12J—C129—H12K109.5
C58—C57—C56124.73 (19)N127—C129—H12L109.5
C58—C57—C77118.64 (18)H12J—C129—H12L109.5
C56—C57—C77116.61 (18)H12K—C129—H12L109.5
N74—C58—C57125.77 (18)O130—C131—N132125.0 (2)
N74—C58—C59109.92 (18)O130—C131—H131117.5
C57—C58—C59124.23 (19)N132—C131—H131117.5
C60—C59—C58107.08 (18)C131—N132—C134120.8 (2)
C60—C59—H59126.5C131—N132—C133120.7 (2)
C58—C59—H59126.5C134—N132—C133118.4 (2)
C59—C60—C61106.61 (19)N132—C133—H13A109.5
C59—C60—H60126.7N132—C133—H13B109.5
C61—C60—H60126.7H13A—C133—H13B109.5
N74—C61—C62126.40 (19)N132—C133—H13C109.5
N74—C61—C60110.42 (18)H13A—C133—H13C109.5
C62—C61—C60123.12 (19)H13B—C133—H13C109.5
C63—C62—C61124.12 (19)N132—C134—H13D109.5
C63—C62—C84117.60 (18)N132—C134—H13E109.5
C61—C62—C84118.27 (18)H13D—C134—H13E109.5
N75—C63—C62125.31 (18)N132—C134—H13F109.5
N75—C63—C64106.59 (17)H13D—C134—H13F109.5
C62—C63—C64128.08 (19)H13E—C134—H13F109.5
C65—C64—C63108.12 (19)O135—C136—N137125.7 (2)
C65—C64—H64125.9O135—C136—H136117.1
C63—C64—H64125.9N137—C136—H136117.1
C64—C65—C66108.63 (19)C136—N137—C138122.4 (2)
C64—C65—H65125.7C136—N137—C139120.5 (2)
C66—C65—H65125.7C138—N137—C139117.1 (2)
N75—C66—C67125.91 (19)N137—C138—H13G109.5
N75—C66—C65106.31 (17)N137—C138—H13H109.5
C67—C66—C65127.75 (19)H13G—C138—H13H109.5
C66—C67—C68125.11 (19)N137—C138—H13I109.5
C66—C67—C91117.07 (18)H13G—C138—H13I109.5
C68—C67—C91117.80 (18)H13H—C138—H13I109.5
N76—C68—C67125.91 (18)N137—C139—H13J109.5
N76—C68—C69110.11 (18)N137—C139—H13K109.5
C67—C68—C69123.96 (19)H13J—C139—H13K109.5
C70—C69—C68106.99 (19)N137—C139—H13L109.5
C70—C69—H69126.5H13J—C139—H13L109.5
C68—C69—H69126.5H13K—C139—H13L109.5
C69—C70—C71106.57 (19)N42A—C41A—O40A151.9 (7)
C69—C70—H70126.7N42A—C41A—H41A104.0
C71—C70—H70126.7O40A—C41A—H41A104.0
N76—C71—C72126.47 (19)C41A—N42A—C44A131.9 (7)
N76—C71—C70110.63 (18)C41A—N42A—C43A115.2 (6)
C72—C71—C70122.90 (19)C44A—N42A—C43A112.6 (5)
C53—C72—C71124.49 (19)O40B—C41B—N42B143.9 (9)
C53—C72—C98119.14 (18)O40B—C41B—H41B108.1
C71—C72—C98116.32 (18)N42B—C41B—H41B108.1
C56—N73—C53110.46 (17)C43B—N42B—C41B126.8 (6)
C56—N73—H73124.8C43B—N42B—C44B119.4 (6)
C53—N73—H73124.8C41B—N42B—C44B113.8 (6)
C61—N74—C58105.82 (16)N42B—C43B—H4AB109.5
C61—N74—H74127.1N42B—C43B—H4BB109.5
C58—N74—H74127.1H4AB—C43B—H4BB109.5
C63—N75—C66110.26 (16)N42B—C43B—H4CB109.5
C63—N75—H75124.9H4AB—C43B—H4CB109.5
C66—N75—H75124.9H4BB—C43B—H4CB109.5
C71—N76—C68105.63 (16)N42B—C44B—H4DB109.5
C71—N76—H76127.2N42B—C44B—H4EB109.5
C68—N76—H76127.2H4DB—C44B—H4EB109.5
C78—C77—C82117.24 (19)N42B—C44B—H4FB109.5
C78—C77—C57122.41 (18)H4DB—C44B—H4FB109.5
C82—C77—C57120.34 (19)H4EB—C44B—H4FB109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O1150.841.802.6366 (18)177
O38—H38···O1250.841.822.6491 (17)171
O45—H45···O1100.841.832.6666 (16)174
O52—H52···O1200.841.832.6686 (18)175
O83—H83···O40A0.841.822.642 (4)166
O83—H83···O40B0.841.892.647 (4)149
O90—H90···O1350.841.862.6929 (18)174
O97—H97···O1050.841.812.6467 (16)174
O104—H104···O1300.841.862.6961 (18)174
(II) 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin N,N'-dimethylformamide tetrasolvate monohydrate top
Crystal data top
C44H30N4O4·4C3H7NO·H2OZ = 2
Mr = 989.12F(000) = 1048
Triclinic, P1Dx = 1.297 Mg m3
a = 12.8346 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.6669 (2) ÅCell parameters from 8903 reflections
c = 15.3200 (3) Åθ = 2.0–28.2°
α = 102.8305 (6)°µ = 0.09 mm1
β = 90.2339 (6)°T = 110 K
γ = 104.3547 (11)°Plate, red
V = 2533.39 (7) Å30.60 × 0.50 × 0.30 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
8881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 28.2°, θmin = 2.0°
Detector resolution: 12.8 pixels mm-1h = 1717
1 deg. ϕ and ω scansk = 1717
26977 measured reflectionsl = 2020
12018 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0787P)2 + 1.1683P]
where P = (Fo2 + 2Fc2)/3
12018 reflections(Δ/σ)max = 0.002
670 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C44H30N4O4·4C3H7NO·H2Oγ = 104.3547 (11)°
Mr = 989.12V = 2533.39 (7) Å3
Triclinic, P1Z = 2
a = 12.8346 (2) ÅMo Kα radiation
b = 13.6669 (2) ŵ = 0.09 mm1
c = 15.3200 (3) ÅT = 110 K
α = 102.8305 (6)°0.60 × 0.50 × 0.30 mm
β = 90.2339 (6)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
8881 reflections with I > 2σ(I)
26977 measured reflectionsRint = 0.030
12018 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.03Δρmax = 0.48 e Å3
12018 reflectionsΔρmin = 0.44 e Å3
670 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.56080 (12)0.19555 (12)0.64950 (10)0.0166 (3)
C20.53238 (13)0.26145 (13)0.72686 (11)0.0185 (3)
H20.55240.26470.78740.022*
C30.47164 (13)0.31892 (13)0.69897 (11)0.0195 (3)
H30.44170.36870.73670.023*
C40.46088 (12)0.29134 (12)0.60344 (11)0.0172 (3)
C50.40455 (12)0.33196 (12)0.54693 (11)0.0168 (3)
C60.41308 (12)0.31675 (12)0.45343 (11)0.0169 (3)
C70.35467 (13)0.35920 (13)0.39555 (11)0.0196 (3)
H70.30040.39490.41240.023*
C80.39269 (13)0.33792 (13)0.31332 (11)0.0201 (3)
H80.37210.35740.26130.024*
C90.47136 (12)0.27930 (12)0.32015 (11)0.0168 (3)
C100.52915 (12)0.24391 (12)0.24701 (10)0.0171 (3)
C110.59708 (12)0.17820 (12)0.24766 (11)0.0178 (3)
C120.65545 (13)0.13922 (13)0.17448 (11)0.0195 (3)
H120.65820.15650.11770.023*
C130.70640 (13)0.07296 (13)0.20033 (11)0.0193 (3)
H130.75040.03560.16440.023*
C140.68251 (12)0.06908 (12)0.29068 (11)0.0171 (3)
C150.71637 (12)0.00875 (12)0.34241 (10)0.0166 (3)
C160.69680 (12)0.01359 (12)0.43354 (11)0.0164 (3)
C170.72678 (13)0.05453 (12)0.48456 (11)0.0184 (3)
H170.75890.11000.46240.022*
C180.70002 (13)0.02331 (12)0.56960 (11)0.0189 (3)
H180.70940.05260.61890.023*
C190.65399 (12)0.06410 (12)0.57066 (10)0.0164 (3)
C200.61980 (12)0.12166 (12)0.64875 (10)0.0164 (3)
N210.51817 (10)0.21809 (10)0.57605 (9)0.0162 (3)
H210.52630.18990.51980.019*0.50
N220.48155 (10)0.26586 (10)0.40497 (9)0.0165 (3)
H220.52310.23180.42450.020*0.50
N230.61723 (10)0.13538 (10)0.31727 (9)0.0168 (3)
H230.59220.14840.37080.020*0.50
N240.65080 (10)0.08352 (10)0.48694 (9)0.0163 (3)
H240.62460.13110.47090.020*0.50
C250.33294 (12)0.39654 (12)0.59124 (10)0.0171 (3)
C260.25298 (13)0.35684 (13)0.64513 (11)0.0191 (3)
H260.24500.28860.65340.023*
C270.18497 (13)0.41550 (13)0.68678 (11)0.0205 (3)
H270.13080.38690.72270.025*
C280.19615 (13)0.51572 (13)0.67598 (11)0.0192 (3)
C290.27533 (13)0.55676 (13)0.62234 (11)0.0195 (3)
H290.28310.62500.61420.023*
C300.34274 (12)0.49744 (12)0.58094 (11)0.0182 (3)
H300.39660.52610.54490.022*
O310.13042 (10)0.57136 (10)0.72111 (9)0.0275 (3)
H310.13060.62210.69850.041*
C320.52238 (13)0.28101 (13)0.16308 (11)0.0183 (3)
C330.57589 (14)0.38248 (13)0.16094 (12)0.0237 (4)
H330.61200.42850.21430.028*
C340.57758 (14)0.41772 (14)0.08266 (12)0.0261 (4)
H340.61570.48680.08240.031*
C350.52334 (15)0.35162 (14)0.00458 (11)0.0249 (4)
C360.46762 (15)0.25109 (14)0.00631 (12)0.0270 (4)
H360.42950.20590.04660.032*
C370.46720 (14)0.21633 (14)0.08461 (11)0.0242 (4)
H370.42870.14740.08480.029*
O380.52169 (13)0.38207 (11)0.07420 (9)0.0345 (3)
H380.56860.43820.07040.052*
C390.78044 (12)0.06297 (12)0.29604 (10)0.0171 (3)
C400.73460 (13)0.14665 (13)0.22490 (11)0.0200 (3)
H400.66100.15860.20620.024*
C410.79400 (13)0.21273 (13)0.18089 (11)0.0212 (3)
H410.76080.26990.13340.025*
C420.90236 (14)0.19482 (13)0.20673 (11)0.0211 (3)
C430.94989 (13)0.11096 (13)0.27621 (12)0.0231 (4)
H431.02420.09780.29350.028*
C440.88926 (13)0.04628 (13)0.32064 (11)0.0213 (3)
H440.92250.01030.36860.026*
O450.96531 (10)0.25729 (10)0.16743 (9)0.0290 (3)
H450.92800.30650.12790.044*
C460.64909 (12)0.10367 (12)0.73713 (10)0.0169 (3)
C470.75628 (13)0.11671 (13)0.76476 (11)0.0192 (3)
H470.81140.13890.72700.023*
C480.78475 (13)0.09814 (13)0.84601 (11)0.0217 (3)
H480.85840.10760.86330.026*
C490.70460 (14)0.06552 (13)0.90199 (11)0.0201 (3)
C500.59727 (14)0.05538 (13)0.87670 (11)0.0212 (3)
H500.54240.03560.91550.025*
C510.57033 (13)0.07397 (12)0.79559 (11)0.0192 (3)
H510.49680.06640.77920.023*
O520.72536 (10)0.04259 (10)0.98108 (8)0.0280 (3)
H520.79220.05890.99300.042*
O530.09389 (10)0.72612 (10)0.65338 (9)0.0316 (3)
C540.11087 (15)0.75753 (13)0.58384 (12)0.0263 (4)
H540.18190.76760.56380.032*
N550.03633 (12)0.77824 (12)0.53496 (11)0.0289 (3)
C560.06214 (18)0.81358 (18)0.45339 (14)0.0406 (5)
H56A0.13790.81700.44230.061*
H56B0.04970.88270.45980.061*
H56C0.01620.76500.40290.061*
C570.07409 (17)0.76465 (19)0.56046 (16)0.0414 (5)
H57A0.07980.74650.61900.062*
H57B0.12150.70890.51550.062*
H57C0.09560.82940.56420.062*
O580.86664 (12)0.42799 (11)0.04797 (10)0.0414 (4)
C590.88094 (19)0.50648 (16)0.06877 (15)0.0395 (5)
H590.90580.49910.12900.047*
N600.86483 (16)0.59908 (13)0.01506 (13)0.0421 (4)
C610.8830 (3)0.6867 (2)0.0472 (2)0.0787 (11)
H61A0.91320.66260.10930.118*
H61B0.93350.71730.00940.118*
H61C0.81440.73900.04430.118*
C620.8298 (2)0.6178 (2)0.07958 (17)0.0527 (6)
H62A0.75280.65320.08840.079*
H62B0.87090.66140.11640.079*
H62C0.84210.55140.09730.079*
O630.93357 (12)0.08821 (13)1.02441 (11)0.0448 (4)
C640.98721 (16)0.09577 (16)1.09406 (14)0.0344 (4)
H640.95070.06811.14050.041*
N651.09128 (13)0.13954 (13)1.10831 (11)0.0317 (4)
C661.14945 (18)0.14594 (18)1.19120 (15)0.0419 (5)
H66A1.10030.11141.23030.063*
H66B1.17930.21901.22130.063*
H66C1.20820.11171.17820.063*
C671.1531 (2)0.1799 (2)1.03880 (18)0.0504 (6)
H67A1.10510.16920.98570.076*
H67B1.20950.14341.02280.076*
H67C1.18620.25421.06110.076*
O680.81306 (16)0.58539 (16)0.20961 (13)0.0637 (5)
C690.86683 (17)0.57297 (18)0.27516 (15)0.0384 (5)
H690.92920.62680.27730.046*
N700.84512 (14)0.49075 (14)0.34320 (14)0.0433 (5)
C710.91475 (19)0.48164 (19)0.41760 (16)0.0456 (5)
H71A0.97060.54680.41130.068*
H71B0.87190.46710.47420.068*
H71C0.94870.42490.41750.068*
C720.7531 (3)0.4046 (3)0.3454 (3)0.1008 (14)
H72A0.70440.42520.29980.151*
H72B0.77720.34600.33310.151*
H72C0.71500.38390.40480.151*
O730.68215 (13)0.55635 (13)0.06864 (12)0.0502 (4)
H73A0.73870.56120.03280.075*
H73B0.72390.56570.11400.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0147 (7)0.0198 (8)0.0157 (8)0.0040 (6)0.0023 (6)0.0054 (6)
C20.0196 (8)0.0217 (8)0.0150 (8)0.0073 (6)0.0025 (6)0.0037 (6)
C30.0198 (8)0.0229 (8)0.0170 (8)0.0087 (6)0.0049 (6)0.0033 (6)
C40.0147 (7)0.0185 (8)0.0189 (8)0.0057 (6)0.0037 (6)0.0034 (6)
C50.0145 (7)0.0178 (8)0.0184 (8)0.0041 (6)0.0032 (6)0.0049 (6)
C60.0147 (7)0.0176 (8)0.0192 (8)0.0051 (6)0.0031 (6)0.0044 (6)
C70.0168 (7)0.0228 (8)0.0209 (8)0.0089 (6)0.0021 (6)0.0044 (6)
C80.0200 (8)0.0236 (8)0.0190 (8)0.0093 (6)0.0003 (6)0.0055 (6)
C90.0158 (7)0.0189 (8)0.0170 (8)0.0058 (6)0.0008 (6)0.0054 (6)
C100.0186 (7)0.0178 (8)0.0160 (8)0.0056 (6)0.0017 (6)0.0053 (6)
C110.0188 (7)0.0190 (8)0.0157 (8)0.0047 (6)0.0012 (6)0.0043 (6)
C120.0211 (8)0.0240 (8)0.0154 (8)0.0081 (6)0.0041 (6)0.0063 (6)
C130.0183 (8)0.0249 (8)0.0168 (8)0.0086 (6)0.0057 (6)0.0055 (6)
C140.0147 (7)0.0198 (8)0.0171 (8)0.0060 (6)0.0016 (6)0.0034 (6)
C150.0148 (7)0.0188 (8)0.0166 (8)0.0062 (6)0.0012 (6)0.0028 (6)
C160.0148 (7)0.0180 (8)0.0169 (8)0.0052 (6)0.0015 (6)0.0039 (6)
C170.0198 (8)0.0180 (8)0.0185 (8)0.0079 (6)0.0012 (6)0.0031 (6)
C180.0211 (8)0.0201 (8)0.0178 (8)0.0078 (6)0.0027 (6)0.0064 (6)
C190.0151 (7)0.0179 (8)0.0170 (8)0.0053 (6)0.0018 (6)0.0044 (6)
C200.0137 (7)0.0190 (8)0.0168 (8)0.0032 (6)0.0016 (6)0.0056 (6)
N210.0177 (6)0.0188 (7)0.0146 (6)0.0088 (5)0.0029 (5)0.0042 (5)
N220.0162 (6)0.0179 (7)0.0174 (7)0.0068 (5)0.0026 (5)0.0054 (5)
N230.0181 (6)0.0206 (7)0.0145 (6)0.0092 (5)0.0024 (5)0.0051 (5)
N240.0172 (6)0.0184 (7)0.0150 (6)0.0072 (5)0.0024 (5)0.0044 (5)
C250.0165 (7)0.0193 (8)0.0160 (8)0.0065 (6)0.0013 (6)0.0031 (6)
C260.0198 (8)0.0193 (8)0.0198 (8)0.0067 (6)0.0026 (6)0.0056 (6)
C270.0187 (8)0.0247 (8)0.0197 (8)0.0074 (6)0.0053 (6)0.0064 (7)
C280.0183 (8)0.0246 (8)0.0163 (8)0.0105 (6)0.0009 (6)0.0022 (6)
C290.0209 (8)0.0197 (8)0.0189 (8)0.0068 (6)0.0014 (6)0.0045 (6)
C300.0165 (7)0.0216 (8)0.0164 (8)0.0051 (6)0.0020 (6)0.0035 (6)
O310.0327 (7)0.0301 (7)0.0277 (7)0.0199 (5)0.0121 (5)0.0096 (5)
C320.0198 (8)0.0229 (8)0.0160 (8)0.0109 (6)0.0035 (6)0.0062 (6)
C330.0266 (9)0.0233 (9)0.0215 (9)0.0058 (7)0.0020 (7)0.0064 (7)
C340.0298 (9)0.0250 (9)0.0268 (9)0.0084 (7)0.0024 (7)0.0111 (7)
C350.0347 (9)0.0304 (9)0.0190 (8)0.0208 (8)0.0081 (7)0.0107 (7)
C360.0395 (10)0.0247 (9)0.0174 (8)0.0120 (7)0.0037 (7)0.0019 (7)
C370.0306 (9)0.0220 (9)0.0208 (9)0.0078 (7)0.0007 (7)0.0055 (7)
O380.0574 (9)0.0344 (8)0.0194 (7)0.0204 (7)0.0064 (6)0.0121 (6)
C390.0189 (7)0.0199 (8)0.0154 (8)0.0088 (6)0.0038 (6)0.0055 (6)
C400.0193 (8)0.0233 (8)0.0187 (8)0.0074 (6)0.0029 (6)0.0052 (6)
C410.0262 (8)0.0198 (8)0.0179 (8)0.0072 (6)0.0065 (6)0.0031 (6)
C420.0262 (8)0.0205 (8)0.0218 (8)0.0127 (6)0.0108 (7)0.0079 (6)
C430.0189 (8)0.0262 (9)0.0266 (9)0.0102 (6)0.0035 (7)0.0058 (7)
C440.0194 (8)0.0232 (8)0.0211 (8)0.0082 (6)0.0000 (6)0.0018 (7)
O450.0296 (7)0.0251 (7)0.0354 (8)0.0156 (5)0.0121 (6)0.0035 (5)
C460.0195 (8)0.0178 (8)0.0145 (8)0.0071 (6)0.0020 (6)0.0031 (6)
C470.0171 (7)0.0224 (8)0.0190 (8)0.0067 (6)0.0040 (6)0.0047 (6)
C480.0197 (8)0.0255 (9)0.0206 (8)0.0090 (6)0.0014 (6)0.0032 (7)
C490.0278 (8)0.0186 (8)0.0152 (8)0.0097 (6)0.0005 (6)0.0024 (6)
C500.0245 (8)0.0224 (8)0.0182 (8)0.0078 (6)0.0064 (6)0.0057 (6)
C510.0173 (7)0.0218 (8)0.0189 (8)0.0060 (6)0.0022 (6)0.0045 (6)
O520.0325 (7)0.0374 (7)0.0181 (6)0.0127 (6)0.0001 (5)0.0103 (5)
O530.0323 (7)0.0300 (7)0.0355 (8)0.0084 (5)0.0009 (6)0.0133 (6)
C540.0272 (9)0.0205 (8)0.0292 (10)0.0037 (7)0.0007 (7)0.0042 (7)
N550.0275 (8)0.0302 (8)0.0280 (8)0.0036 (6)0.0011 (6)0.0089 (7)
C560.0461 (12)0.0410 (12)0.0297 (11)0.0022 (9)0.0056 (9)0.0130 (9)
C570.0302 (10)0.0564 (14)0.0412 (12)0.0130 (9)0.0002 (9)0.0166 (11)
O580.0490 (9)0.0322 (8)0.0435 (9)0.0196 (7)0.0070 (7)0.0010 (6)
C590.0531 (13)0.0295 (11)0.0320 (11)0.0091 (9)0.0147 (9)0.0003 (8)
N600.0532 (11)0.0266 (9)0.0416 (10)0.0089 (8)0.0159 (9)0.0007 (7)
C610.153 (3)0.0309 (13)0.0527 (17)0.0229 (16)0.0308 (19)0.0118 (12)
C620.0555 (15)0.0491 (14)0.0488 (14)0.0271 (11)0.0089 (11)0.0138 (11)
O630.0374 (8)0.0505 (9)0.0470 (9)0.0152 (7)0.0132 (7)0.0082 (7)
C640.0307 (10)0.0386 (11)0.0348 (11)0.0102 (8)0.0001 (8)0.0086 (9)
N650.0293 (8)0.0334 (9)0.0320 (9)0.0062 (7)0.0022 (7)0.0090 (7)
C660.0420 (12)0.0385 (12)0.0422 (13)0.0110 (9)0.0145 (10)0.0024 (9)
C670.0450 (13)0.0508 (14)0.0546 (15)0.0024 (11)0.0117 (11)0.0211 (12)
O680.0700 (12)0.0766 (13)0.0644 (12)0.0361 (10)0.0432 (10)0.0369 (10)
C690.0366 (11)0.0422 (12)0.0448 (12)0.0156 (9)0.0121 (9)0.0207 (10)
N700.0299 (9)0.0355 (10)0.0603 (13)0.0010 (7)0.0076 (8)0.0109 (9)
C710.0418 (12)0.0456 (13)0.0421 (13)0.0061 (10)0.0036 (10)0.0005 (10)
C720.060 (2)0.0536 (19)0.169 (4)0.0155 (15)0.034 (2)0.017 (2)
O730.0487 (9)0.0542 (10)0.0644 (11)0.0254 (8)0.0270 (8)0.0338 (9)
Geometric parameters (Å, º) top
C1—N211.376 (2)C39—C401.396 (2)
C1—C201.403 (2)C40—C411.388 (2)
C1—C21.429 (2)C40—H400.9500
C2—C31.363 (2)C41—C421.391 (2)
C2—H20.9500C41—H410.9500
C3—C41.425 (2)C42—O451.3645 (19)
C3—H30.9500C42—C431.387 (2)
C4—N211.3785 (19)C43—C441.389 (2)
C4—C51.410 (2)C43—H430.9500
C5—C61.410 (2)C44—H440.9500
C5—C251.492 (2)O45—H450.8400
C6—N221.3735 (19)C46—C471.394 (2)
C6—C71.457 (2)C46—C511.398 (2)
C7—C81.350 (2)C47—C481.389 (2)
C7—H70.9500C47—H470.9500
C8—C91.453 (2)C48—C491.394 (2)
C8—H80.9500C48—H480.9500
C9—N221.362 (2)C49—O521.358 (2)
C9—C101.408 (2)C49—C501.394 (2)
C10—C111.400 (2)C50—C511.382 (2)
C10—C321.493 (2)C50—H500.9500
C11—N231.377 (2)C51—H510.9500
C11—C121.429 (2)O52—H520.8400
C12—C131.362 (2)O53—C541.235 (2)
C12—H120.9500C54—N551.334 (2)
C13—C141.429 (2)C54—H540.9500
C13—H130.9500N55—C561.448 (3)
C14—N231.3800 (19)N55—C571.450 (3)
C14—C151.401 (2)C56—H56A0.9800
C15—C161.410 (2)C56—H56B0.9800
C15—C391.496 (2)C56—H56C0.9800
C16—N241.3666 (19)C57—H57A0.9800
C16—C171.457 (2)C57—H57B0.9800
C17—C181.352 (2)C57—H57C0.9800
C17—H170.9500O58—C591.239 (3)
C18—C191.455 (2)C59—N601.314 (3)
C18—H180.9500C59—H590.9500
C19—N241.369 (2)N60—C611.459 (3)
C19—C201.414 (2)N60—C621.464 (3)
C20—C461.492 (2)C61—H61A0.9800
N21—H210.8800C61—H61B0.9800
N22—H220.8800C61—H61C0.9800
N23—H230.8800C62—H62A0.9800
N24—H240.8800C62—H62B0.9800
C25—C301.398 (2)C62—H62C0.9800
C25—C261.400 (2)O63—C641.238 (2)
C26—C271.391 (2)C64—N651.316 (3)
C26—H260.9500C64—H640.9500
C27—C281.388 (2)N65—C661.445 (3)
C27—H270.9500N65—C671.455 (3)
C28—O311.3629 (19)C66—H66A0.9800
C28—C291.397 (2)C66—H66B0.9800
C29—C301.390 (2)C66—H66C0.9800
C29—H290.9500C67—H67A0.9800
C30—H300.9500C67—H67B0.9800
O31—H310.8400C67—H67C0.9800
C32—C371.392 (2)O68—C691.225 (3)
C32—C331.394 (2)C69—N701.323 (3)
C33—C341.386 (2)C69—H690.9500
C33—H330.9500N70—C721.441 (3)
C34—C351.390 (3)N70—C711.454 (3)
C34—H340.9500C71—H71A0.9800
C35—O381.363 (2)C71—H71B0.9800
C35—C361.389 (3)C71—H71C0.9800
C36—C371.384 (2)C72—H72A0.9800
C36—H360.9500C72—H72B0.9800
C37—H370.9500C72—H72C0.9800
O38—H380.8400O73—H73A0.8887
C39—C441.394 (2)O73—H73B0.8919
N21—C1—C20126.78 (14)C44—C39—C15120.90 (14)
N21—C1—C2106.60 (13)C40—C39—C15121.33 (14)
C20—C1—C2126.62 (14)C41—C40—C39121.60 (15)
C3—C2—C1108.33 (14)C41—C40—H40119.2
C3—C2—H2125.8C39—C40—H40119.2
C1—C2—H2125.8C40—C41—C42119.69 (15)
C2—C3—C4108.17 (14)C40—C41—H41120.2
C2—C3—H3125.9C42—C41—H41120.2
C4—C3—H3125.9O45—C42—C43117.49 (15)
N21—C4—C5126.06 (14)O45—C42—C41122.93 (15)
N21—C4—C3106.81 (13)C43—C42—C41119.57 (14)
C5—C4—C3127.11 (14)C42—C43—C44120.23 (15)
C6—C5—C4124.51 (14)C42—C43—H43119.9
C6—C5—C25119.05 (14)C44—C43—H43119.9
C4—C5—C25116.43 (14)C43—C44—C39121.16 (16)
N22—C6—C5125.28 (14)C43—C44—H44119.4
N22—C6—C7110.47 (14)C39—C44—H44119.4
C5—C6—C7124.14 (14)C42—O45—H45109.5
C8—C7—C6106.58 (14)C47—C46—C51117.55 (14)
C8—C7—H7126.7C47—C46—C20121.13 (14)
C6—C7—H7126.7C51—C46—C20121.31 (14)
C7—C8—C9106.33 (14)C48—C47—C46121.83 (14)
C7—C8—H8126.8C48—C47—H47119.1
C9—C8—H8126.8C46—C47—H47119.1
N22—C9—C10126.09 (14)C47—C48—C49119.59 (15)
N22—C9—C8111.25 (13)C47—C48—H48120.2
C10—C9—C8122.66 (14)C49—C48—H48120.2
C11—C10—C9124.67 (14)O52—C49—C48123.26 (15)
C11—C10—C32116.30 (13)O52—C49—C50117.46 (14)
C9—C10—C32118.99 (13)C48—C49—C50119.27 (15)
N23—C11—C10126.85 (14)C51—C50—C49120.36 (15)
N23—C11—C12106.81 (13)C51—C50—H50119.8
C10—C11—C12126.30 (15)C49—C50—H50119.8
C13—C12—C11108.14 (14)C50—C51—C46121.32 (15)
C13—C12—H12125.9C50—C51—H51119.3
C11—C12—H12125.9C46—C51—H51119.3
C12—C13—C14108.43 (14)C49—O52—H52109.5
C12—C13—H13125.8O53—C54—N55124.46 (17)
C14—C13—H13125.8O53—C54—H54117.8
N23—C14—C15126.15 (14)N55—C54—H54117.8
N23—C14—C13106.57 (13)C54—N55—C56121.25 (17)
C15—C14—C13127.27 (14)C54—N55—C57121.42 (16)
C14—C15—C16124.79 (14)C56—N55—C57117.32 (17)
C14—C15—C39115.97 (14)N55—C56—H56A109.5
C16—C15—C39119.21 (14)N55—C56—H56B109.5
N24—C16—C15125.51 (14)H56A—C56—H56B109.5
N24—C16—C17110.61 (13)N55—C56—H56C109.5
C15—C16—C17123.85 (14)H56A—C56—H56C109.5
C18—C17—C16106.61 (14)H56B—C56—H56C109.5
C18—C17—H17126.7N55—C57—H57A109.5
C16—C17—H17126.7N55—C57—H57B109.5
C17—C18—C19106.36 (14)H57A—C57—H57B109.5
C17—C18—H18126.8N55—C57—H57C109.5
C19—C18—H18126.8H57A—C57—H57C109.5
N24—C19—C20125.33 (14)H57B—C57—H57C109.5
N24—C19—C18110.81 (13)O58—C59—N60125.9 (2)
C20—C19—C18123.85 (14)O58—C59—H59117.1
C1—C20—C19124.78 (14)N60—C59—H59117.1
C1—C20—C46117.21 (13)C59—N60—C61121.3 (2)
C19—C20—C46118.01 (13)C59—N60—C62121.3 (2)
C1—N21—C4110.02 (13)C61—N60—C62117.5 (2)
C1—N21—H21125.0N60—C61—H61A109.5
C4—N21—H21125.0N60—C61—H61B109.5
C9—N22—C6105.29 (13)H61A—C61—H61B109.5
C9—N22—H22127.4N60—C61—H61C109.5
C6—N22—H22127.4H61A—C61—H61C109.5
C11—N23—C14110.02 (13)H61B—C61—H61C109.5
C11—N23—H23125.0N60—C62—H62A109.5
C14—N23—H23125.0N60—C62—H62B109.5
C16—N24—C19105.57 (13)H62A—C62—H62B109.5
C16—N24—H24127.2N60—C62—H62C109.5
C19—N24—H24127.2H62A—C62—H62C109.5
C30—C25—C26117.82 (14)H62B—C62—H62C109.5
C30—C25—C5121.95 (14)O63—C64—N65124.6 (2)
C26—C25—C5120.23 (14)O63—C64—H64117.7
C27—C26—C25121.22 (15)N65—C64—H64117.7
C27—C26—H26119.4C64—N65—C66121.95 (18)
C25—C26—H26119.4C64—N65—C67120.64 (19)
C28—C27—C26120.12 (15)C66—N65—C67117.37 (18)
C28—C27—H27119.9N65—C66—H66A109.5
C26—C27—H27119.9N65—C66—H66B109.5
O31—C28—C27117.79 (14)H66A—C66—H66B109.5
O31—C28—C29122.62 (15)N65—C66—H66C109.5
C27—C28—C29119.56 (14)H66A—C66—H66C109.5
C30—C29—C28119.84 (15)H66B—C66—H66C109.5
C30—C29—H29120.1N65—C67—H67A109.5
C28—C29—H29120.1N65—C67—H67B109.5
C29—C30—C25121.43 (15)H67A—C67—H67B109.5
C29—C30—H30119.3N65—C67—H67C109.5
C25—C30—H30119.3H67A—C67—H67C109.5
C28—O31—H31109.5H67B—C67—H67C109.5
C37—C32—C33118.01 (15)O68—C69—N70125.4 (2)
C37—C32—C10122.21 (15)O68—C69—H69117.3
C33—C32—C10119.74 (15)N70—C69—H69117.3
C34—C33—C32121.46 (16)C69—N70—C72121.3 (2)
C34—C33—H33119.3C69—N70—C71121.64 (18)
C32—C33—H33119.3C72—N70—C71117.0 (2)
C33—C34—C35119.75 (17)N70—C71—H71A109.5
C33—C34—H34120.1N70—C71—H71B109.5
C35—C34—H34120.1H71A—C71—H71B109.5
O38—C35—C36118.26 (17)N70—C71—H71C109.5
O38—C35—C34122.37 (17)H71A—C71—H71C109.5
C36—C35—C34119.37 (16)H71B—C71—H71C109.5
C37—C36—C35120.46 (16)N70—C72—H72A109.5
C37—C36—H36119.8N70—C72—H72B109.5
C35—C36—H36119.8H72A—C72—H72B109.5
C36—C37—C32120.93 (16)N70—C72—H72C109.5
C36—C37—H37119.5H72A—C72—H72C109.5
C32—C37—H37119.5H72B—C72—H72C109.5
C35—O38—H38109.5H73A—O73—H73B91.5
C44—C39—C40117.74 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O530.841.872.6891 (18)166
O38—H38···O730.841.882.720 (2)175
O45—H45···O580.841.822.649 (2)168
O52—H52···O630.841.802.6356 (19)176
O73—H73B···O680.891.892.779 (2)180
O73—H73A···O58i0.892.012.896 (2)180
Symmetry code: (i) x, y+1, z.
(III) 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin N,N'-dimethylformamide hexasolvate dihydrate top
Crystal data top
C44H30N4O4·6C4H9NO·2H2OF(000) = 2648
Mr = 1237.48Dx = 1.242 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 35.5243 (8) ÅCell parameters from 5086 reflections
b = 6.5265 (2) Åθ = 1.4–25.5°
c = 29.2172 (9) ŵ = 0.09 mm1
β = 102.2713 (10)°T = 110 K
V = 6619.2 (3) Å3Needle, red
Z = 40.50 × 0.15 × 0.15 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4359 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 25.5°, θmin = 2.5°
Detector resolution: 12.8 pixels mm-1h = 042
1 deg. ϕ and ω scansk = 07
16577 measured reflectionsl = 3534
6116 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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0425P)2 + 19.1457P]
where P = (Fo2 + 2Fc2)/3
6116 reflections(Δ/σ)max = 0.001
418 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
C44H30N4O4·6C4H9NO·2H2OV = 6619.2 (3) Å3
Mr = 1237.48Z = 4
Monoclinic, C2/cMo Kα radiation
a = 35.5243 (8) ŵ = 0.09 mm1
b = 6.5265 (2) ÅT = 110 K
c = 29.2172 (9) Å0.50 × 0.15 × 0.15 mm
β = 102.2713 (10)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
4359 reflections with I > 2σ(I)
16577 measured reflectionsRint = 0.050
6116 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0425P)2 + 19.1457P]
where P = (Fo2 + 2Fc2)/3
6116 reflectionsΔρmax = 0.78 e Å3
418 parametersΔρmin = 0.48 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.21114 (7)0.1110 (4)1.07824 (8)0.0190 (5)
C20.18595 (7)0.0466 (4)1.09006 (9)0.0228 (6)
H20.17720.05791.11850.027*
C30.17734 (7)0.1731 (4)1.05305 (9)0.0228 (6)
H30.16140.29111.05020.027*
C40.19723 (7)0.0944 (4)1.01820 (8)0.0190 (5)
C50.19437 (7)0.1876 (4)0.97390 (8)0.0187 (5)
C60.21534 (7)0.1279 (4)0.94078 (8)0.0200 (6)
C70.21310 (7)0.2141 (4)0.89528 (8)0.0208 (6)
H70.19800.32900.88260.025*
C80.23633 (7)0.1027 (4)0.87340 (9)0.0221 (6)
H80.24060.12840.84290.026*
C90.25316 (7)0.0591 (4)0.90362 (8)0.0192 (5)
C100.27562 (7)0.2215 (4)0.89262 (8)0.0193 (5)
N110.21785 (6)0.0769 (3)1.03433 (7)0.0193 (5)
H110.23240.15011.01960.023*0.50
N120.24047 (6)0.0356 (3)0.94474 (7)0.0180 (5)
H120.24740.11310.96980.022*0.50
C130.16497 (7)0.3524 (4)0.95977 (8)0.0201 (6)
C140.12583 (7)0.3075 (4)0.95262 (9)0.0271 (6)
H140.11800.17130.95720.033*
C150.09809 (8)0.4570 (4)0.93896 (10)0.0306 (7)
H150.07160.42210.93380.037*
C160.10887 (8)0.6570 (4)0.93277 (9)0.0271 (6)
C170.14775 (7)0.7045 (4)0.93893 (9)0.0272 (6)
H170.15550.84080.93410.033*
C180.17518 (7)0.5537 (4)0.95200 (9)0.0241 (6)
H180.20170.58790.95580.029*
O190.08300 (5)0.8139 (3)0.92116 (8)0.0384 (5)
H190.06050.76860.91870.058*
C200.28576 (7)0.2143 (4)0.84547 (8)0.0199 (6)
C210.30836 (7)0.0564 (4)0.83368 (8)0.0217 (6)
H210.31620.05210.85530.026*
C220.31965 (7)0.0542 (4)0.79092 (9)0.0239 (6)
H220.33500.05480.78350.029*
C230.30832 (7)0.2122 (4)0.75902 (9)0.0245 (6)
C240.28455 (7)0.3669 (4)0.76948 (9)0.0246 (6)
H240.27580.47230.74730.029*
C250.27360 (7)0.3670 (4)0.81223 (9)0.0231 (6)
H250.25740.47360.81910.028*
O260.31952 (6)0.2234 (3)0.71726 (6)0.0317 (5)
H260.33640.13430.71650.048*
O270.00849 (6)0.7389 (4)0.90642 (9)0.0627 (8)
H27A0.00990.66880.91730.094*
H27B0.00450.81580.87980.094*
O280.04741 (6)0.5393 (4)0.93692 (9)0.0519 (6)
C290.04581 (9)0.3544 (5)0.94799 (11)0.0392 (8)
C300.00757 (9)0.2453 (6)0.96095 (14)0.0538 (10)
H30A0.01310.33890.95710.081*
H30B0.00780.12590.94060.081*
H30C0.00320.20030.99370.081*
N310.07745 (7)0.2487 (4)0.94935 (9)0.0360 (6)
C320.11481 (8)0.3509 (5)0.93940 (12)0.0423 (8)
H32A0.11120.49770.93490.063*
H32B0.12750.33080.96580.063*
H32C0.13090.29280.91090.063*
C330.07684 (9)0.0330 (5)0.96300 (13)0.0480 (9)
H33A0.06630.02070.99670.072*
H33B0.06070.04460.94580.072*
H33C0.10310.02180.95570.072*
O340.03218 (8)0.9012 (4)0.82393 (10)0.0709 (8)
C350.05666 (16)1.0450 (9)0.82158 (14)0.0814 (14)
C360.09979 (11)1.0061 (7)0.81677 (17)0.0787 (14)
H36A0.11431.08300.78990.118*
H36B0.10761.05110.84540.118*
H36C0.10510.85940.81200.118*
N370.04804 (13)1.2275 (6)0.82317 (12)0.0833 (12)
C380.07399 (12)1.4063 (6)0.81956 (14)0.0619 (11)
H38A0.09291.38340.83900.093*
H38B0.08741.42480.78690.093*
H38C0.05891.52920.83040.093*
C390.00403 (12)1.2764 (8)0.8273 (2)0.0993 (18)
H39A0.00071.30700.79620.149*
H39B0.01141.15750.84040.149*
H39C0.00321.39500.84780.149*
O400.37692 (6)0.0156 (3)0.70913 (7)0.0357 (5)
C410.37196 (8)0.1965 (5)0.69484 (10)0.0312 (7)
C420.33209 (9)0.2814 (5)0.68095 (12)0.0423 (8)
H42A0.31370.18200.68850.063*
H42B0.32600.30880.64720.063*
H42C0.33040.40920.69800.063*
N430.40173 (7)0.3143 (4)0.69138 (9)0.0402 (7)
C440.39836 (11)0.5285 (5)0.67616 (15)0.0582 (11)
H44A0.37120.57000.67000.087*
H44B0.40820.54340.64750.087*
H44C0.41330.61540.70080.087*
C450.44083 (9)0.2311 (6)0.70293 (13)0.0538 (10)
H45A0.43970.08110.70210.081*
H45B0.45370.27660.73430.081*
H45C0.45530.27990.68010.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0189 (12)0.0183 (14)0.0191 (13)0.0018 (11)0.0026 (10)0.0023 (11)
C20.0255 (14)0.0249 (15)0.0191 (13)0.0020 (12)0.0076 (11)0.0014 (11)
C30.0234 (13)0.0216 (14)0.0234 (13)0.0048 (12)0.0051 (10)0.0021 (11)
C40.0182 (12)0.0172 (14)0.0208 (13)0.0014 (11)0.0020 (10)0.0017 (11)
C50.0185 (12)0.0150 (13)0.0219 (13)0.0026 (11)0.0029 (10)0.0015 (11)
C60.0200 (13)0.0173 (14)0.0220 (13)0.0020 (11)0.0027 (10)0.0004 (11)
C70.0204 (13)0.0203 (14)0.0206 (13)0.0003 (11)0.0017 (10)0.0021 (11)
C80.0251 (13)0.0221 (15)0.0191 (13)0.0003 (12)0.0052 (11)0.0016 (11)
C90.0195 (12)0.0204 (14)0.0167 (12)0.0039 (11)0.0016 (10)0.0001 (11)
C100.0191 (12)0.0205 (14)0.0177 (12)0.0026 (11)0.0031 (10)0.0010 (11)
N110.0206 (11)0.0187 (12)0.0189 (11)0.0015 (10)0.0045 (9)0.0001 (9)
N120.0204 (11)0.0170 (11)0.0171 (10)0.0007 (9)0.0049 (8)0.0010 (9)
C130.0236 (13)0.0207 (14)0.0166 (12)0.0001 (12)0.0056 (10)0.0006 (11)
C140.0266 (14)0.0208 (15)0.0347 (15)0.0005 (13)0.0084 (12)0.0028 (12)
C150.0197 (14)0.0289 (17)0.0422 (17)0.0012 (13)0.0046 (12)0.0033 (14)
C160.0286 (15)0.0218 (15)0.0294 (14)0.0085 (13)0.0030 (12)0.0038 (12)
C170.0273 (15)0.0188 (15)0.0335 (15)0.0011 (13)0.0023 (12)0.0016 (12)
C180.0202 (13)0.0217 (15)0.0290 (14)0.0016 (12)0.0019 (11)0.0016 (12)
O190.0267 (10)0.0273 (12)0.0583 (14)0.0060 (10)0.0025 (10)0.0075 (10)
C200.0197 (13)0.0201 (14)0.0187 (12)0.0021 (11)0.0017 (10)0.0012 (11)
C210.0244 (13)0.0203 (14)0.0196 (13)0.0006 (12)0.0026 (10)0.0023 (11)
C220.0249 (14)0.0253 (15)0.0225 (13)0.0030 (12)0.0073 (11)0.0015 (12)
C230.0262 (14)0.0293 (16)0.0179 (13)0.0005 (13)0.0043 (11)0.0004 (12)
C240.0283 (14)0.0266 (16)0.0180 (13)0.0010 (12)0.0031 (11)0.0043 (11)
C250.0234 (13)0.0225 (15)0.0238 (13)0.0008 (12)0.0057 (11)0.0004 (11)
O260.0406 (12)0.0364 (12)0.0213 (9)0.0105 (10)0.0139 (8)0.0056 (9)
O270.0295 (12)0.0660 (18)0.0893 (19)0.0021 (12)0.0049 (12)0.0318 (15)
O280.0400 (13)0.0383 (15)0.0778 (17)0.0015 (11)0.0132 (12)0.0124 (13)
C290.0353 (17)0.037 (2)0.0444 (18)0.0014 (16)0.0066 (14)0.0045 (15)
C300.0292 (17)0.050 (2)0.081 (3)0.0032 (17)0.0081 (17)0.016 (2)
N310.0263 (13)0.0347 (15)0.0459 (15)0.0015 (12)0.0056 (11)0.0054 (12)
C320.0295 (16)0.044 (2)0.053 (2)0.0072 (15)0.0076 (14)0.0018 (16)
C330.0346 (18)0.035 (2)0.073 (2)0.0009 (16)0.0082 (17)0.0133 (18)
O340.0729 (18)0.0622 (19)0.0756 (19)0.0339 (16)0.0114 (15)0.0076 (15)
C350.117 (4)0.081 (4)0.046 (2)0.014 (3)0.015 (2)0.006 (2)
C360.042 (2)0.086 (3)0.107 (4)0.004 (2)0.015 (2)0.004 (3)
N370.132 (4)0.061 (3)0.054 (2)0.014 (3)0.015 (2)0.0031 (19)
C380.071 (3)0.050 (2)0.060 (2)0.017 (2)0.005 (2)0.002 (2)
C390.061 (3)0.092 (4)0.155 (5)0.025 (3)0.044 (3)0.015 (4)
O400.0366 (12)0.0332 (13)0.0397 (12)0.0018 (10)0.0138 (9)0.0069 (10)
C410.0380 (17)0.0306 (17)0.0282 (15)0.0038 (15)0.0139 (13)0.0008 (13)
C420.0402 (18)0.0356 (19)0.053 (2)0.0073 (16)0.0136 (15)0.0031 (16)
N430.0391 (15)0.0339 (15)0.0536 (17)0.0033 (13)0.0237 (13)0.0002 (13)
C440.071 (3)0.0285 (19)0.087 (3)0.0064 (18)0.044 (2)0.0013 (19)
C450.0380 (19)0.058 (2)0.070 (2)0.0039 (18)0.0222 (17)0.002 (2)
Geometric parameters (Å, º) top
C1—N111.372 (3)O26—H260.8400
C1—C10i1.404 (4)O27—H27A0.9074
C1—C21.452 (4)O27—H27B0.9569
C2—C31.343 (4)O28—C291.248 (4)
C2—H20.9500C29—N311.327 (4)
C3—C41.451 (3)C29—C301.509 (4)
C3—H30.9500C30—H30A0.9800
C4—N111.365 (3)C30—H30B0.9800
C4—C51.414 (3)C30—H30C0.9800
C5—C61.396 (3)N31—C321.458 (4)
C5—C131.495 (4)N31—C331.462 (4)
C6—N121.380 (3)C32—H32A0.9800
C6—C71.430 (3)C32—H32B0.9800
C7—C81.357 (4)C32—H32C0.9800
C7—H70.9500C33—H33A0.9800
C8—C91.424 (4)C33—H33B0.9800
C8—H80.9500C33—H33C0.9800
C9—N121.379 (3)O34—C351.271 (6)
C9—C101.404 (4)C35—N371.228 (6)
C10—C1i1.404 (4)C35—C361.530 (6)
C10—C201.497 (3)C36—H36A0.9800
N11—H110.8800C36—H36B0.9800
N12—H120.8800C36—H36C0.9800
C13—C141.393 (4)N37—C381.477 (5)
C13—C181.394 (4)N37—C391.575 (6)
C14—C151.384 (4)C38—H38A0.9800
C14—H140.9500C38—H38B0.9800
C15—C161.383 (4)C38—H38C0.9800
C15—H150.9500C39—H39A0.9800
C16—O191.370 (3)C39—H39B0.9800
C16—C171.389 (4)C39—H39C0.9800
C17—C181.380 (4)O40—C411.252 (3)
C17—H170.9500C41—N431.329 (4)
C18—H180.9500C41—C421.494 (4)
O19—H190.8400C42—H42A0.9800
C20—C251.395 (4)C42—H42B0.9800
C20—C211.394 (4)C42—H42C0.9800
C21—C221.391 (3)N43—C451.463 (4)
C21—H210.9500N43—C441.464 (4)
C22—C231.391 (4)C44—H44A0.9800
C22—H220.9500C44—H44B0.9800
C23—O261.364 (3)C44—H44C0.9800
C23—C241.391 (4)C45—H45A0.9800
C24—C251.385 (3)C45—H45B0.9800
C24—H240.9500C45—H45C0.9800
C25—H250.9500
N11—C1—C10i126.2 (2)H27A—O27—H27B107.0
N11—C1—C2110.2 (2)O28—C29—N31121.2 (3)
C10i—C1—C2123.4 (2)O28—C29—C30120.7 (3)
C3—C2—C1106.9 (2)N31—C29—C30118.1 (3)
C3—C2—H2126.6C29—C30—H30A109.5
C1—C2—H2126.6C29—C30—H30B109.5
C2—C3—C4106.6 (2)H30A—C30—H30B109.5
C2—C3—H3126.7C29—C30—H30C109.5
C4—C3—H3126.7H30A—C30—H30C109.5
N11—C4—C5126.7 (2)H30B—C30—H30C109.5
N11—C4—C3110.7 (2)C29—N31—C32119.8 (3)
C5—C4—C3122.6 (2)C29—N31—C33123.0 (3)
C6—C5—C4124.7 (2)C32—N31—C33117.1 (3)
C6—C5—C13117.0 (2)N31—C32—H32A109.5
C4—C5—C13118.2 (2)N31—C32—H32B109.5
N12—C6—C5126.0 (2)H32A—C32—H32B109.5
N12—C6—C7106.8 (2)N31—C32—H32C109.5
C5—C6—C7127.0 (2)H32A—C32—H32C109.5
C8—C7—C6107.9 (2)H32B—C32—H32C109.5
C8—C7—H7126.0N31—C33—H33A109.5
C6—C7—H7126.0N31—C33—H33B109.5
C7—C8—C9108.8 (2)H33A—C33—H33B109.5
C7—C8—H8125.6N31—C33—H33C109.5
C9—C8—H8125.6H33A—C33—H33C109.5
N12—C9—C10126.2 (2)H33B—C33—H33C109.5
N12—C9—C8106.6 (2)N37—C35—O34123.5 (5)
C10—C9—C8127.0 (2)N37—C35—C36113.6 (5)
C9—C10—C1i125.6 (2)O34—C35—C36122.9 (5)
C9—C10—C20116.5 (2)C35—C36—H36A109.5
C1i—C10—C20117.9 (2)C35—C36—H36B109.5
C4—N11—C1105.6 (2)H36A—C36—H36B109.5
C4—N11—H11127.2C35—C36—H36C109.5
C1—N11—H11127.2H36A—C36—H36C109.5
C9—N12—C6109.8 (2)H36B—C36—H36C109.5
C9—N12—H12125.1C35—N37—C38128.1 (5)
C6—N12—H12125.1C35—N37—C39115.8 (5)
C14—C13—C18117.4 (2)C38—N37—C39116.1 (4)
C14—C13—C5120.4 (2)N37—C38—H38A109.5
C18—C13—C5122.2 (2)N37—C38—H38B109.5
C15—C14—C13121.5 (3)H38A—C38—H38B109.5
C15—C14—H14119.3N37—C38—H38C109.5
C13—C14—H14119.3H38A—C38—H38C109.5
C14—C15—C16120.2 (3)H38B—C38—H38C109.5
C14—C15—H15119.9N37—C39—H39A109.5
C16—C15—H15119.9N37—C39—H39B109.5
O19—C16—C15123.2 (2)H39A—C39—H39B109.5
O19—C16—C17117.5 (2)N37—C39—H39C109.5
C15—C16—C17119.3 (2)H39A—C39—H39C109.5
C18—C17—C16120.1 (3)H39B—C39—H39C109.5
C18—C17—H17120.0O40—C41—N43120.9 (3)
C16—C17—H17120.0O40—C41—C42119.9 (3)
C17—C18—C13121.6 (2)N43—C41—C42119.2 (3)
C17—C18—H18119.2C41—C42—H42A109.5
C13—C18—H18119.2C41—C42—H42B109.5
C16—O19—H19109.5H42A—C42—H42B109.5
C25—C20—C21117.8 (2)C41—C42—H42C109.5
C25—C20—C10121.3 (2)H42A—C42—H42C109.5
C21—C20—C10121.0 (2)H42B—C42—H42C109.5
C22—C21—C20121.4 (2)C41—N43—C45120.0 (3)
C22—C21—H21119.3C41—N43—C44124.1 (3)
C20—C21—H21119.3C45—N43—C44115.9 (3)
C23—C22—C21119.8 (2)N43—C44—H44A109.5
C23—C22—H22120.1N43—C44—H44B109.5
C21—C22—H22120.1H44A—C44—H44B109.5
O26—C23—C22122.8 (2)N43—C44—H44C109.5
O26—C23—C24117.6 (2)H44A—C44—H44C109.5
C22—C23—C24119.6 (2)H44B—C44—H44C109.5
C25—C24—C23119.9 (2)N43—C45—H45A109.5
C25—C24—H24120.1N43—C45—H45B109.5
C23—C24—H24120.1H45A—C45—H45B109.5
C24—C25—C20121.5 (2)N43—C45—H45C109.5
C24—C25—H25119.2H45A—C45—H45C109.5
C20—C25—H25119.2H45B—C45—H45C109.5
C23—O26—H26109.5
Symmetry code: (i) x+1/2, y1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O19—H19···O270.841.822.636 (3)164
O26—H26···O400.841.792.618 (3)168
O27—H27A···O280.911.772.681 (3)177
O27—H27B···O340.961.812.745 (4)166

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC44H30N4O4·4C3H7NOC44H30N4O4·4C3H7NO·H2OC44H30N4O4·6C4H9NO·2H2O
Mr971.10989.121237.48
Crystal system, space groupTriclinic, P1Triclinic, P1Monoclinic, C2/c
Temperature (K)110110110
a, b, c (Å)13.6255 (2), 16.0184 (3), 26.2466 (5)12.8346 (2), 13.6669 (2), 15.3200 (3)35.5243 (8), 6.5265 (2), 29.2172 (9)
α, β, γ (°)101.7445 (12), 92.4786 (12), 114.9158 (8)102.8305 (6), 90.2339 (6), 104.3547 (11)90, 102.2713 (10), 90
V3)5032.65 (15)2533.39 (7)6619.2 (3)
Z424
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.090.09
Crystal size (mm)0.40 × 0.40 × 0.200.60 × 0.50 × 0.300.50 × 0.15 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
50610, 23879, 13053 26977, 12018, 8881 16577, 6116, 4359
Rint0.0510.0300.050
(sin θ/λ)max1)0.6580.6640.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.169, 1.04 0.053, 0.153, 1.03 0.069, 0.154, 1.03
No. of reflections23877120186116
No. of parameters1370670418
No. of restraints1800
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0777P)2 + 0.4228P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0787P)2 + 1.1683P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0425P)2 + 19.1457P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.36, 0.390.48, 0.440.78, 0.48

Computer programs: [Please provide details], COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SIR97 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O1150.841.802.6366 (18)177
O38—H38···O1250.841.822.6491 (17)171
O45—H45···O1100.841.832.6666 (16)174
O52—H52···O1200.841.832.6686 (18)175
O83—H83···O40A0.841.822.642 (4)166
O83—H83···O40B0.841.892.647 (4)149
O90—H90···O1350.841.862.6929 (18)174
O97—H97···O1050.841.812.6467 (16)174
O104—H104···O1300.841.862.6961 (18)174
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O530.841.872.6891 (18)166
O38—H38···O730.841.882.720 (2)175
O45—H45···O580.841.822.649 (2)168
O52—H52···O630.841.802.6356 (19)176
O73—H73B···O680.891.892.779 (2)180
O73—H73A···O58i0.892.012.896 (2)180
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O19—H19···O270.841.822.636 (3)164
O26—H26···O400.841.792.618 (3)168
O27—H27A···O280.911.772.681 (3)177
O27—H27B···O340.961.812.745 (4)166
 

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