Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021071/sj2285sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021071/sj2285Isup2.hkl |
CCDC reference: 657793
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- Disorder in solvent or counterion
- R factor = 0.054
- wR factor = 0.151
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT411_ALERT_2_B Short Inter H...H Contact H1 .. H7D .. 2.08 Ang. PLAT415_ALERT_2_B Short Inter D-H..H-X H1BB .. H4DA .. 1.95 Ang.
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.608 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.61 e/A PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 40.00 Perc. PLAT416_ALERT_2_C Short Intra D-H..H-D H1BB .. H2BA .. 1.94 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1B .. C4D .. 2.97 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3A .. C5D .. 2.96 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 26
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1B = ... R
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Thomas E Ray carried out the synthetic work. Dr. Ralph N. Salvatore designed the synthetic method Dr. Eric. E. Dueno supervised the work of Ray; he is also the principal investigator. Dr. M. Zeller and Dr. A.D. Hunter carried out the crystallization and Xray diffraction analysis Dr. C. Zambrano wrote the text -manuscript- for the cif and prepared the cif file and figures |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
A 50 ml round bottom flask was charged with 2.0 g (16 mmol) pyrogallol and 11 ml 95% ethanol. The reaction vessel was cooled in an ice bath to 0 °C and 2.0 ml of concentrated HCl was added in one portion. 4-hydroxybenzaldehyde (2.0 g, 17 mmol) was then added dropwise over a period of 10 minutes. The reaction vessel was allowed to warm slowly to room temperature and then maintained at 80 °C for 12 h, the pink precipitate that separated was collected by filtration and washed with cold 1:1 ethanol-water until the material was pale and neutral to pH paper. Drying under vacuum at 40 °C for 12 h afforded 10.3 g (28 mmol) of 2,8,14,20-para-hydroxytetra(phenyl)pyrogallol [4]arene, Yield, 70% mp >400 °C. Crystals suitable for X-ray diffraction were grown from a solution of the title compound in DMF by vapor diffusion of ether over a period of three days.
Two solvate DMF molecules are flip-disordered by an approximate 180° rotation around the axis built by the oxygen and nitrogen atom. The occupancy ratios are 0.853 (2) to 0.147 (2) and 0.862 (2) to 0.138 (2), respectively. Atoms of the minor components were set to have the same anisotropic displacement parameters as their major component counterparts.
All hydrogen atoms were placed in calculated positions and were refined with an isotropic displacement parameter 1.5 (methyl, hydroxyl) or 1.2 times (all others) that of the adjacent carbon or oxygen atom. Methyl and hydroxyl H atoms were allowed to rotate to best fit the experimental electron density.
Calix-shaped compounds such as pyrogallolarenes have received considerable attention during the last two decades due to their potential use in a number of industrial applications (Asfari et al., 2001). The conformational isomers of pyrogallol[4]arenes are being studied by various investigators (Makeiff & Sherman, 2005, and references therein). Our investigations have shown that aryl-substituted pyrogallol[4]arenes adopt a chair (rctt) conformation (Zambrano et al., 2006; Kass et al., 2006), whereas alkyl substituents lead to the crown (rccc) structure (Dueno et al., 2006). Here, we report the crystal structure of the compound 2,8,14,20-para-hydroxytetraphenylpyrogallol[4]arene as its hexa DMF solvate, (1).
The title compound (1) lies on an inversion center. The molecule exhibits a chair (rctt) conformation, characteristic of pyrogallol[4]arenes with aromatic substituents. In this molecule, the pyrogallol ring (C2A to C7A) is separated from its symmetry inverse ring (C2Avi to C7Ai, symmetry code vi = -x, 1 - y, 1 - z) by a distance of 4.934 (2) Å, based on least squares mean planes of both rings. The other two pyrogallol rings (C2B to C7B and C2Bvi to C7Bvi) show an interplanar distance of 0.340 (2) Å. The dihedral angle between the pyrogallol rings not related by symmetry (C2A to C7A and C2B to C7B) is 83.64 (15)°, which indicates that the chair structure is slightly distorted from an ideal, right-angle chair conformation. Another interesting structural feature of this molecule is the position of the p-hydroxyphenyl substituents which are almost perfectly aligned one on top of the other, as in our previously reported compounds (Zambrano et al., 2006). The centroid to centroid distance of the p-hydroxyphenyl rings (C8A to C13A and C8B to C13B) is 4.168 (2) Å, which suggests that there is no π-π interaction (Figure 1).
The asymmetric part of the unit cell contains three molecules of DMF, which are acting as hydrogen bond acceptors for a number the hydroxyl groups of the pyrogallolarene macrocycle and the OH group from the p-hydroxyphenyl substituents (Table 1). The hydrogen-bond distances are all unexceptional (Cave et al., 2005), and these interactions contribute to the stability and molecular arrangement in the crystal packing (Figure 2).
For details of calix-shaped compounds and their applications, see: Asfari et al. (2001). For related structures, see: Makeiff & Sherman (2005, and references therein), Zambrano et al. (2006); Kass et al. (2006), Dueno et al. (2006) and Cave et al. (2005).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C52H40O16·6C3H7NO | Z = 1 |
Mr = 1359.42 | F(000) = 720 |
Triclinic, P1 | Dx = 1.372 Mg m−3 |
a = 10.6481 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.5153 (6) Å | Cell parameters from 6320 reflections |
c = 14.3315 (7) Å | θ = 2.5–30.5° |
α = 75.748 (1)° | µ = 0.10 mm−1 |
β = 78.462 (1)° | T = 100 K |
γ = 77.891 (1)° | Rod, red |
V = 1644.8 (1) Å3 | 0.44 × 0.25 × 0.19 mm |
Bruker SMART APEX CCD diffractometer | 8127 independent reflections |
Radiation source: fine-focus sealed tube | 7050 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 28.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003) | h = −14→14 |
Tmin = 0.914, Tmax = 0.981 | k = −15→15 |
17256 measured reflections | l = −19→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0801P)2 + 0.915P] where P = (Fo2 + 2Fc2)/3 |
8127 reflections | (Δ/σ)max = 0.001 |
472 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C52H40O16·6C3H7NO | γ = 77.891 (1)° |
Mr = 1359.42 | V = 1644.8 (1) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.6481 (5) Å | Mo Kα radiation |
b = 11.5153 (6) Å | µ = 0.10 mm−1 |
c = 14.3315 (7) Å | T = 100 K |
α = 75.748 (1)° | 0.44 × 0.25 × 0.19 mm |
β = 78.462 (1)° |
Bruker SMART APEX CCD diffractometer | 8127 independent reflections |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003) | 7050 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.981 | Rint = 0.018 |
17256 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.61 e Å−3 |
8127 reflections | Δρmin = −0.30 e Å−3 |
472 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.99258 (17) | 0.38850 (15) | 0.28575 (12) | 0.0307 (3) | |
H1 | 0.9761 | 0.3275 | 0.3427 | 0.037* | |
C2 | 0.99254 (17) | 0.60148 (15) | 0.21092 (12) | 0.0312 (3) | |
H2A | 1.0539 | 0.5683 | 0.1594 | 0.047* | |
H2B | 1.0306 | 0.6599 | 0.2313 | 0.047* | |
H2C | 0.9116 | 0.6425 | 0.1862 | 0.047* | |
C3 | 0.8999 (2) | 0.53525 (18) | 0.38644 (13) | 0.0384 (4) | |
H3A | 0.8920 | 0.4611 | 0.4368 | 0.058* | |
H3B | 0.8131 | 0.5821 | 0.3786 | 0.058* | |
H3C | 0.9511 | 0.5844 | 0.4058 | 0.058* | |
C1A | 0.34385 (13) | 1.16631 (13) | −0.21626 (10) | 0.0201 (3) | |
H1A | 0.2936 | 1.2428 | −0.2507 | 0.024* | |
C2A | 0.30150 (13) | 1.15892 (13) | −0.10722 (10) | 0.0194 (3) | |
C3A | 0.27753 (13) | 1.05079 (12) | −0.04233 (10) | 0.0185 (3) | |
H3AA | 0.2871 | 0.9799 | −0.0675 | 0.022* | |
C4A | 0.24032 (13) | 1.04211 (12) | 0.05747 (10) | 0.0193 (3) | |
C5A | 0.23045 (15) | 1.14616 (13) | 0.09418 (11) | 0.0236 (3) | |
C6A | 0.25611 (16) | 1.25525 (13) | 0.03091 (12) | 0.0256 (3) | |
C7A | 0.28926 (14) | 1.26157 (13) | −0.06914 (11) | 0.0225 (3) | |
C8A | 0.31036 (14) | 1.06105 (13) | −0.24771 (10) | 0.0213 (3) | |
C9A | 0.39940 (15) | 0.95642 (14) | −0.25773 (11) | 0.0252 (3) | |
H9AA | 0.4855 | 0.9499 | −0.2457 | 0.030* | |
C10A | 0.36493 (16) | 0.86066 (15) | −0.28505 (12) | 0.0290 (3) | |
H10A | 0.4269 | 0.7894 | −0.2914 | 0.035* | |
C11A | 0.23889 (16) | 0.87018 (16) | −0.30292 (12) | 0.0293 (3) | |
C12A | 0.14689 (15) | 0.97112 (17) | −0.28887 (12) | 0.0301 (3) | |
H12A | 0.0599 | 0.9758 | −0.2980 | 0.036* | |
C13A | 0.18252 (15) | 1.06538 (15) | −0.26145 (11) | 0.0259 (3) | |
H13A | 0.1189 | 1.1345 | −0.2517 | 0.031* | |
C1B | 0.20447 (13) | 0.92516 (12) | 0.12616 (10) | 0.0183 (3) | |
H1BA | 0.1150 | 0.9462 | 0.1621 | 0.022* | |
C2B | 0.29434 (13) | 0.87096 (12) | 0.20181 (10) | 0.0185 (3) | |
C3B | 0.42568 (13) | 0.87979 (12) | 0.18023 (10) | 0.0193 (3) | |
H3BA | 0.4574 | 0.9261 | 0.1187 | 0.023* | |
C4B | 0.51240 (13) | 0.82355 (13) | 0.24508 (10) | 0.0198 (3) | |
C5B | 0.46533 (14) | 0.75684 (14) | 0.33598 (11) | 0.0232 (3) | |
C6B | 0.33437 (15) | 0.74490 (14) | 0.35918 (10) | 0.0237 (3) | |
C7B | 0.24947 (14) | 0.80255 (13) | 0.29214 (10) | 0.0211 (3) | |
C8B | 0.19900 (14) | 0.83211 (12) | 0.06797 (10) | 0.0199 (3) | |
C9B | 0.30959 (16) | 0.75285 (14) | 0.03820 (12) | 0.0273 (3) | |
H9BA | 0.3888 | 0.7511 | 0.0599 | 0.033* | |
C10B | 0.30687 (18) | 0.67616 (15) | −0.02249 (13) | 0.0343 (4) | |
H10B | 0.3832 | 0.6224 | −0.0417 | 0.041* | |
C11B | 0.1916 (2) | 0.67914 (14) | −0.05453 (12) | 0.0329 (4) | |
C12B | 0.08049 (17) | 0.75720 (15) | −0.02619 (12) | 0.0308 (3) | |
H12B | 0.0016 | 0.7592 | −0.0484 | 0.037* | |
C13B | 0.08468 (15) | 0.83274 (14) | 0.03490 (11) | 0.0253 (3) | |
H13B | 0.0080 | 0.8858 | 0.0544 | 0.030* | |
O2 | 0.42629 (13) | 0.61912 (13) | 0.59274 (9) | 0.0381 (3) | 0.862 (2) |
N2 | 0.57745 (14) | 0.54857 (13) | 0.69391 (10) | 0.0295 (3) | 0.862 (2) |
C4 | 0.46452 (18) | 0.55243 (16) | 0.66588 (13) | 0.0269 (4) | 0.862 (2) |
H4A | 0.4090 | 0.4989 | 0.7060 | 0.032* | 0.862 (2) |
C5 | 0.6704 (2) | 0.6228 (3) | 0.63664 (19) | 0.0496 (6) | 0.862 (2) |
H5A | 0.6324 | 0.6787 | 0.5821 | 0.074* | 0.862 (2) |
H5B | 0.7486 | 0.5707 | 0.6114 | 0.074* | 0.862 (2) |
H5C | 0.6937 | 0.6694 | 0.6774 | 0.074* | 0.862 (2) |
C6 | 0.6104 (2) | 0.46902 (19) | 0.78485 (15) | 0.0345 (4) | 0.862 (2) |
H6A | 0.5418 | 0.4202 | 0.8145 | 0.052* | 0.862 (2) |
H6B | 0.6183 | 0.5182 | 0.8296 | 0.052* | 0.862 (2) |
H6C | 0.6932 | 0.4151 | 0.7716 | 0.052* | 0.862 (2) |
O2D | 0.42629 (13) | 0.61912 (13) | 0.59274 (9) | 0.0381 (3) | 0.138 (2) |
N2D | 0.57745 (14) | 0.54857 (13) | 0.69391 (10) | 0.0295 (3) | 0.138 (2) |
C4D | 0.5417 (12) | 0.5776 (10) | 0.6090 (9) | 0.0269 (4) | 0.138 (2) |
H4DA | 0.6069 | 0.5670 | 0.5545 | 0.032* | 0.138 (2) |
C5D | 0.5114 (15) | 0.5265 (17) | 0.7842 (12) | 0.0496 (6) | 0.138 (2) |
H5DA | 0.4178 | 0.5478 | 0.7817 | 0.074* | 0.138 (2) |
H5DB | 0.5349 | 0.5754 | 0.8231 | 0.074* | 0.138 (2) |
H5DC | 0.5329 | 0.4401 | 0.8141 | 0.074* | 0.138 (2) |
C6D | 0.7317 (13) | 0.5371 (12) | 0.6899 (10) | 0.0345 (4) | 0.138 (2) |
H6DA | 0.7763 | 0.5327 | 0.6238 | 0.052* | 0.138 (2) |
H6DB | 0.7631 | 0.4632 | 0.7358 | 0.052* | 0.138 (2) |
H6DC | 0.7494 | 0.6082 | 0.7078 | 0.052* | 0.138 (2) |
O3 | 0.96416 (13) | 0.75896 (13) | 0.49257 (9) | 0.0406 (3) | 0.853 (2) |
N3 | 0.79212 (15) | 0.90216 (15) | 0.53217 (11) | 0.0371 (3) | 0.853 (2) |
C7 | 0.85173 (19) | 0.81247 (19) | 0.48894 (13) | 0.0308 (4) | 0.853 (2) |
H7 | 0.8032 | 0.7866 | 0.4513 | 0.037* | 0.853 (2) |
C8 | 0.8588 (3) | 0.9613 (2) | 0.58079 (18) | 0.0502 (6) | 0.853 (2) |
H8A | 0.9448 | 0.9129 | 0.5892 | 0.075* | 0.853 (2) |
H8B | 0.8081 | 0.9687 | 0.6448 | 0.075* | 0.853 (2) |
H8C | 0.8688 | 1.0424 | 0.5414 | 0.075* | 0.853 (2) |
C9 | 0.6571 (2) | 0.9574 (3) | 0.5217 (2) | 0.0562 (7) | 0.853 (2) |
H9A | 0.6524 | 1.0446 | 0.4938 | 0.084* | 0.853 (2) |
H9B | 0.6024 | 0.9454 | 0.5858 | 0.084* | 0.853 (2) |
H9C | 0.6264 | 0.9191 | 0.4785 | 0.084* | 0.853 (2) |
O3D | 0.96416 (13) | 0.75896 (13) | 0.49257 (9) | 0.0406 (3) | 0.147 (2) |
N3D | 0.79212 (15) | 0.90216 (15) | 0.53217 (11) | 0.0371 (3) | 0.147 (2) |
C7D | 0.9189 (11) | 0.8283 (11) | 0.5317 (8) | 0.0308 (4) | 0.147 (2) |
H7D | 0.9706 | 0.8438 | 0.5727 | 0.037* | 0.147 (2) |
C8D | 0.6903 (18) | 0.8547 (14) | 0.5047 (10) | 0.0502 (6) | 0.147 (2) |
H8DA | 0.7294 | 0.7831 | 0.4771 | 0.075* | 0.147 (2) |
H8DB | 0.6470 | 0.9175 | 0.4561 | 0.075* | 0.147 (2) |
H8DC | 0.6264 | 0.8320 | 0.5625 | 0.075* | 0.147 (2) |
C9D | 0.7601 (15) | 0.9996 (16) | 0.5765 (12) | 0.0562 (7) | 0.147 (2) |
H9DA | 0.8377 | 1.0356 | 0.5707 | 0.084* | 0.147 (2) |
H9DB | 0.7261 | 0.9723 | 0.6455 | 0.084* | 0.147 (2) |
H9DC | 0.6936 | 1.0604 | 0.5449 | 0.084* | 0.147 (2) |
N1 | 0.96491 (13) | 0.50275 (12) | 0.29420 (10) | 0.0270 (3) | |
O1 | 1.03927 (14) | 0.35553 (11) | 0.20722 (9) | 0.0385 (3) | |
O1A | 0.19421 (13) | 1.13827 (10) | 0.19257 (8) | 0.0329 (3) | |
H1AC | 0.1457 | 1.2031 | 0.2027 | 0.049* | |
O2A | 0.25105 (14) | 1.36112 (10) | 0.06166 (9) | 0.0355 (3) | |
H2AA | 0.1883 | 1.3681 | 0.1071 | 0.053* | |
O3A | 0.31120 (12) | 1.36937 (10) | −0.13166 (8) | 0.0281 (2) | |
H3AB | 0.2624 | 1.4275 | −0.1101 | 0.042* | |
O4A | 0.20173 (13) | 0.78266 (13) | −0.33659 (10) | 0.0398 (3) | |
H4AA | 0.2328 | 0.7135 | −0.3067 | 0.060* | |
O1B | 0.55232 (11) | 0.70030 (12) | 0.39992 (8) | 0.0332 (3) | |
H1BB | 0.5112 | 0.6779 | 0.4558 | 0.050* | |
O2B | 0.28093 (12) | 0.67351 (12) | 0.44388 (8) | 0.0347 (3) | |
H2BA | 0.3294 | 0.6603 | 0.4863 | 0.052* | |
O3B | 0.12134 (10) | 0.78879 (11) | 0.31362 (8) | 0.0270 (2) | |
H3BB | 0.0963 | 0.7814 | 0.3739 | 0.041* | |
O4B | 0.19297 (16) | 0.60331 (12) | −0.11610 (11) | 0.0466 (4) | |
H4BB | 0.1199 | 0.6163 | −0.1340 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0415 (9) | 0.0288 (8) | 0.0254 (7) | −0.0126 (7) | −0.0070 (6) | −0.0052 (6) |
C2 | 0.0360 (9) | 0.0252 (7) | 0.0307 (8) | −0.0053 (6) | −0.0042 (6) | −0.0035 (6) |
C3 | 0.0432 (10) | 0.0424 (10) | 0.0304 (9) | −0.0062 (8) | −0.0005 (7) | −0.0143 (8) |
C1A | 0.0194 (6) | 0.0204 (6) | 0.0205 (6) | −0.0040 (5) | −0.0056 (5) | −0.0019 (5) |
C2A | 0.0172 (6) | 0.0209 (6) | 0.0206 (6) | −0.0027 (5) | −0.0052 (5) | −0.0039 (5) |
C3A | 0.0167 (6) | 0.0176 (6) | 0.0223 (6) | −0.0015 (5) | −0.0055 (5) | −0.0053 (5) |
C4A | 0.0178 (6) | 0.0178 (6) | 0.0225 (7) | −0.0009 (5) | −0.0061 (5) | −0.0040 (5) |
C5A | 0.0278 (7) | 0.0216 (7) | 0.0220 (7) | −0.0012 (5) | −0.0065 (5) | −0.0062 (5) |
C6A | 0.0319 (8) | 0.0197 (7) | 0.0280 (7) | −0.0033 (6) | −0.0085 (6) | −0.0083 (6) |
C7A | 0.0230 (7) | 0.0189 (6) | 0.0261 (7) | −0.0039 (5) | −0.0066 (5) | −0.0032 (5) |
C8A | 0.0215 (7) | 0.0260 (7) | 0.0174 (6) | −0.0068 (5) | −0.0040 (5) | −0.0034 (5) |
C9A | 0.0232 (7) | 0.0286 (7) | 0.0266 (7) | −0.0060 (6) | −0.0064 (6) | −0.0076 (6) |
C10A | 0.0294 (8) | 0.0294 (8) | 0.0313 (8) | −0.0053 (6) | −0.0050 (6) | −0.0116 (6) |
C11A | 0.0319 (8) | 0.0356 (8) | 0.0261 (7) | −0.0140 (7) | −0.0024 (6) | −0.0118 (6) |
C12A | 0.0225 (7) | 0.0438 (9) | 0.0292 (8) | −0.0106 (6) | −0.0033 (6) | −0.0139 (7) |
C13A | 0.0215 (7) | 0.0340 (8) | 0.0238 (7) | −0.0052 (6) | −0.0034 (5) | −0.0087 (6) |
C1B | 0.0171 (6) | 0.0188 (6) | 0.0190 (6) | −0.0014 (5) | −0.0036 (5) | −0.0049 (5) |
C2B | 0.0198 (6) | 0.0179 (6) | 0.0187 (6) | −0.0023 (5) | −0.0042 (5) | −0.0051 (5) |
C3B | 0.0215 (6) | 0.0179 (6) | 0.0186 (6) | −0.0040 (5) | −0.0041 (5) | −0.0025 (5) |
C4B | 0.0189 (6) | 0.0201 (6) | 0.0215 (6) | −0.0046 (5) | −0.0047 (5) | −0.0040 (5) |
C5B | 0.0243 (7) | 0.0250 (7) | 0.0208 (7) | −0.0044 (5) | −0.0081 (5) | −0.0023 (5) |
C6B | 0.0255 (7) | 0.0282 (7) | 0.0172 (6) | −0.0081 (6) | −0.0034 (5) | −0.0012 (5) |
C7B | 0.0205 (6) | 0.0244 (7) | 0.0195 (6) | −0.0054 (5) | −0.0024 (5) | −0.0061 (5) |
C8B | 0.0241 (7) | 0.0170 (6) | 0.0188 (6) | −0.0046 (5) | −0.0054 (5) | −0.0019 (5) |
C9B | 0.0297 (8) | 0.0257 (7) | 0.0284 (8) | 0.0027 (6) | −0.0117 (6) | −0.0096 (6) |
C10B | 0.0429 (10) | 0.0270 (8) | 0.0341 (9) | 0.0094 (7) | −0.0164 (7) | −0.0135 (7) |
C11B | 0.0555 (11) | 0.0200 (7) | 0.0276 (8) | −0.0038 (7) | −0.0199 (7) | −0.0046 (6) |
C12B | 0.0366 (9) | 0.0281 (8) | 0.0323 (8) | −0.0105 (6) | −0.0152 (7) | −0.0029 (6) |
C13B | 0.0241 (7) | 0.0248 (7) | 0.0275 (7) | −0.0056 (6) | −0.0062 (6) | −0.0038 (6) |
O2 | 0.0399 (7) | 0.0472 (7) | 0.0287 (6) | −0.0062 (6) | −0.0114 (5) | −0.0072 (5) |
N2 | 0.0339 (7) | 0.0274 (7) | 0.0256 (7) | −0.0041 (5) | −0.0073 (5) | −0.0015 (5) |
C4 | 0.0315 (9) | 0.0239 (8) | 0.0256 (8) | −0.0048 (7) | −0.0059 (7) | −0.0048 (7) |
C5 | 0.0383 (12) | 0.0636 (16) | 0.0439 (13) | −0.0232 (11) | −0.0095 (10) | 0.0092 (11) |
C6 | 0.0394 (11) | 0.0323 (10) | 0.0311 (10) | −0.0034 (8) | −0.0144 (8) | −0.0005 (8) |
O2D | 0.0399 (7) | 0.0472 (7) | 0.0287 (6) | −0.0062 (6) | −0.0114 (5) | −0.0072 (5) |
N2D | 0.0339 (7) | 0.0274 (7) | 0.0256 (7) | −0.0041 (5) | −0.0073 (5) | −0.0015 (5) |
C4D | 0.0315 (9) | 0.0239 (8) | 0.0256 (8) | −0.0048 (7) | −0.0059 (7) | −0.0048 (7) |
C5D | 0.0383 (12) | 0.0636 (16) | 0.0439 (13) | −0.0232 (11) | −0.0095 (10) | 0.0092 (11) |
C6D | 0.0394 (11) | 0.0323 (10) | 0.0311 (10) | −0.0034 (8) | −0.0144 (8) | −0.0005 (8) |
O3 | 0.0375 (7) | 0.0518 (8) | 0.0267 (6) | 0.0025 (6) | −0.0026 (5) | −0.0080 (6) |
N3 | 0.0381 (8) | 0.0426 (8) | 0.0258 (7) | −0.0014 (7) | 0.0001 (6) | −0.0071 (6) |
C7 | 0.0320 (10) | 0.0377 (10) | 0.0201 (8) | −0.0069 (8) | −0.0019 (7) | −0.0022 (7) |
C8 | 0.0756 (19) | 0.0436 (13) | 0.0323 (11) | −0.0084 (12) | −0.0094 (11) | −0.0104 (10) |
C9 | 0.0368 (12) | 0.0651 (17) | 0.0442 (13) | 0.0104 (11) | 0.0074 (10) | 0.0029 (12) |
O3D | 0.0375 (7) | 0.0518 (8) | 0.0267 (6) | 0.0025 (6) | −0.0026 (5) | −0.0080 (6) |
N3D | 0.0381 (8) | 0.0426 (8) | 0.0258 (7) | −0.0014 (7) | 0.0001 (6) | −0.0071 (6) |
C7D | 0.0320 (10) | 0.0377 (10) | 0.0201 (8) | −0.0069 (8) | −0.0019 (7) | −0.0022 (7) |
C8D | 0.0756 (19) | 0.0436 (13) | 0.0323 (11) | −0.0084 (12) | −0.0094 (11) | −0.0104 (10) |
C9D | 0.0368 (12) | 0.0651 (17) | 0.0442 (13) | 0.0104 (11) | 0.0074 (10) | 0.0029 (12) |
N1 | 0.0316 (7) | 0.0275 (6) | 0.0238 (6) | −0.0081 (5) | −0.0037 (5) | −0.0068 (5) |
O1 | 0.0587 (8) | 0.0298 (6) | 0.0296 (6) | −0.0093 (6) | −0.0064 (6) | −0.0101 (5) |
O1A | 0.0539 (8) | 0.0221 (5) | 0.0219 (5) | −0.0017 (5) | −0.0061 (5) | −0.0072 (4) |
O2A | 0.0559 (8) | 0.0219 (5) | 0.0320 (6) | −0.0101 (5) | −0.0051 (5) | −0.0103 (5) |
O3A | 0.0371 (6) | 0.0188 (5) | 0.0278 (6) | −0.0067 (4) | −0.0046 (5) | −0.0028 (4) |
O4A | 0.0379 (7) | 0.0434 (7) | 0.0486 (8) | −0.0140 (6) | −0.0073 (6) | −0.0229 (6) |
O1B | 0.0267 (6) | 0.0477 (7) | 0.0216 (5) | −0.0097 (5) | −0.0090 (4) | 0.0066 (5) |
O2B | 0.0306 (6) | 0.0508 (7) | 0.0198 (5) | −0.0151 (5) | −0.0059 (4) | 0.0065 (5) |
O3B | 0.0204 (5) | 0.0380 (6) | 0.0215 (5) | −0.0086 (4) | −0.0008 (4) | −0.0031 (4) |
O4B | 0.0759 (10) | 0.0280 (6) | 0.0459 (8) | 0.0043 (6) | −0.0357 (7) | −0.0164 (6) |
C1—O1 | 1.251 (2) | C9B—C10B | 1.391 (2) |
C1—N1 | 1.317 (2) | C9B—H9BA | 0.9500 |
C1—H1 | 0.9500 | C10B—C11B | 1.385 (3) |
C2—N1 | 1.461 (2) | C10B—H10B | 0.9500 |
C2—H2A | 0.9800 | C11B—O4B | 1.3822 (19) |
C2—H2B | 0.9800 | C11B—C12B | 1.384 (3) |
C2—H2C | 0.9800 | C12B—C13B | 1.390 (2) |
C3—N1 | 1.461 (2) | C12B—H12B | 0.9500 |
C3—H3A | 0.9800 | C13B—H13B | 0.9500 |
C3—H3B | 0.9800 | O2—C4 | 1.224 (2) |
C3—H3C | 0.9800 | N2—C4 | 1.331 (2) |
C1A—C8A | 1.5212 (19) | N2—C5 | 1.438 (3) |
C1A—C2A | 1.5236 (19) | N2—C6 | 1.456 (2) |
C1A—C4Bi | 1.5249 (19) | C4—H4A | 0.9500 |
C1A—H1A | 1.0000 | C5—H5A | 0.9800 |
C2A—C7A | 1.392 (2) | C5—H5B | 0.9800 |
C2A—C3A | 1.3959 (19) | C5—H5C | 0.9800 |
C3A—C4A | 1.390 (2) | C6—H6A | 0.9800 |
C3A—H3AA | 0.9500 | C6—H6B | 0.9800 |
C4A—C5A | 1.400 (2) | C6—H6C | 0.9800 |
C4A—C1B | 1.5300 (19) | C4D—H4DA | 0.9500 |
C5A—O1A | 1.3710 (18) | C5D—H5DA | 0.9800 |
C5A—C6A | 1.400 (2) | C5D—H5DB | 0.9800 |
C6A—O2A | 1.3823 (18) | C5D—H5DC | 0.9800 |
C6A—C7A | 1.394 (2) | C6D—H6DA | 0.9800 |
C7A—O3A | 1.3742 (18) | C6D—H6DB | 0.9800 |
C8A—C9A | 1.387 (2) | C6D—H6DC | 0.9800 |
C8A—C13A | 1.403 (2) | O3—C7 | 1.231 (2) |
C9A—C10A | 1.394 (2) | N3—C7 | 1.318 (3) |
C9A—H9AA | 0.9500 | N3—C8 | 1.445 (3) |
C10A—C11A | 1.393 (2) | N3—C9 | 1.466 (3) |
C10A—H10A | 0.9500 | C7—H7 | 0.9500 |
C11A—O4A | 1.3742 (19) | C8—H8A | 0.9800 |
C11A—C12A | 1.382 (2) | C8—H8B | 0.9800 |
C12A—C13A | 1.385 (2) | C8—H8C | 0.9800 |
C12A—H12A | 0.9500 | C9—H9A | 0.9800 |
C13A—H13A | 0.9500 | C9—H9B | 0.9800 |
C1B—C2B | 1.5205 (18) | C9—H9C | 0.9800 |
C1B—C8B | 1.5273 (19) | C7D—H7D | 0.9500 |
C1B—H1BA | 1.0000 | C8D—H8DA | 0.9800 |
C2B—C3B | 1.3903 (19) | C8D—H8DB | 0.9800 |
C2B—C7B | 1.3904 (19) | C8D—H8DC | 0.9800 |
C3B—C4B | 1.3900 (19) | C9D—H9DA | 0.9800 |
C3B—H3BA | 0.9500 | C9D—H9DB | 0.9800 |
C4B—C5B | 1.395 (2) | C9D—H9DC | 0.9800 |
C4B—C1Ai | 1.5249 (19) | O1A—H1AC | 0.8400 |
C5B—O1B | 1.3836 (17) | O2A—H2AA | 0.8400 |
C5B—C6B | 1.395 (2) | O3A—H3AB | 0.8400 |
C6B—O2B | 1.3791 (18) | O4A—H4AA | 0.8400 |
C6B—C7B | 1.401 (2) | O1B—H1BB | 0.8400 |
C7B—O3B | 1.3711 (17) | O2B—H2BA | 0.8400 |
C8B—C13B | 1.390 (2) | O3B—H3BB | 0.8400 |
C8B—C9B | 1.393 (2) | O4B—H4BB | 0.8400 |
O1—C1—N1 | 123.91 (16) | C3B—C2B—C1B | 121.21 (12) |
O1—C1—H1 | 118.0 | C7B—C2B—C1B | 120.64 (12) |
N1—C1—H1 | 118.0 | C4B—C3B—C2B | 122.67 (13) |
N1—C2—H2A | 109.5 | C4B—C3B—H3BA | 118.7 |
N1—C2—H2B | 109.5 | C2B—C3B—H3BA | 118.7 |
H2A—C2—H2B | 109.5 | C3B—C4B—C5B | 118.62 (13) |
N1—C2—H2C | 109.5 | C3B—C4B—C1Ai | 120.30 (12) |
H2A—C2—H2C | 109.5 | C5B—C4B—C1Ai | 121.08 (12) |
H2B—C2—H2C | 109.5 | O1B—C5B—C4B | 118.34 (13) |
N1—C3—H3A | 109.5 | O1B—C5B—C6B | 121.62 (13) |
N1—C3—H3B | 109.5 | C4B—C5B—C6B | 120.00 (13) |
H3A—C3—H3B | 109.5 | O2B—C6B—C5B | 124.23 (13) |
N1—C3—H3C | 109.5 | O2B—C6B—C7B | 115.71 (13) |
H3A—C3—H3C | 109.5 | C5B—C6B—C7B | 119.98 (13) |
H3B—C3—H3C | 109.5 | O3B—C7B—C2B | 118.98 (13) |
C8A—C1A—C2A | 111.44 (11) | O3B—C7B—C6B | 120.22 (13) |
C8A—C1A—C4Bi | 112.76 (12) | C2B—C7B—C6B | 120.76 (13) |
C2A—C1A—C4Bi | 110.53 (11) | C13B—C8B—C9B | 117.86 (13) |
C8A—C1A—H1A | 107.3 | C13B—C8B—C1B | 120.08 (13) |
C2A—C1A—H1A | 107.3 | C9B—C8B—C1B | 121.76 (13) |
C4Bi—C1A—H1A | 107.3 | C10B—C9B—C8B | 121.61 (15) |
C7A—C2A—C3A | 117.90 (13) | C10B—C9B—H9BA | 119.2 |
C7A—C2A—C1A | 119.84 (13) | C8B—C9B—H9BA | 119.2 |
C3A—C2A—C1A | 122.23 (12) | C11B—C10B—C9B | 119.20 (16) |
C4A—C3A—C2A | 122.99 (13) | C11B—C10B—H10B | 120.4 |
C4A—C3A—H3AA | 118.5 | C9B—C10B—H10B | 120.4 |
C2A—C3A—H3AA | 118.5 | O4B—C11B—C12B | 121.99 (16) |
C3A—C4A—C5A | 118.02 (13) | O4B—C11B—C10B | 117.68 (16) |
C3A—C4A—C1B | 122.04 (12) | C12B—C11B—C10B | 120.33 (15) |
C5A—C4A—C1B | 119.87 (13) | C11B—C12B—C13B | 119.74 (15) |
O1A—C5A—C4A | 118.40 (13) | C11B—C12B—H12B | 120.1 |
O1A—C5A—C6A | 121.47 (13) | C13B—C12B—H12B | 120.1 |
C4A—C5A—C6A | 120.13 (13) | C8B—C13B—C12B | 121.25 (15) |
O2A—C6A—C7A | 116.13 (13) | C8B—C13B—H13B | 119.4 |
O2A—C6A—C5A | 123.60 (14) | C12B—C13B—H13B | 119.4 |
C7A—C6A—C5A | 120.27 (13) | C4—N2—C5 | 121.66 (16) |
O3A—C7A—C2A | 118.98 (13) | C4—N2—C6 | 120.65 (16) |
O3A—C7A—C6A | 120.38 (13) | C5—N2—C6 | 117.69 (17) |
C2A—C7A—C6A | 120.64 (13) | O2—C4—N2 | 125.45 (17) |
C9A—C8A—C13A | 117.89 (14) | O2—C4—H4A | 117.3 |
C9A—C8A—C1A | 122.63 (13) | N2—C4—H4A | 117.3 |
C13A—C8A—C1A | 119.36 (13) | H5DA—C5D—H5DB | 109.5 |
C8A—C9A—C10A | 121.21 (14) | H5DA—C5D—H5DC | 109.5 |
C8A—C9A—H9AA | 119.4 | H5DB—C5D—H5DC | 109.5 |
C10A—C9A—H9AA | 119.4 | H6DA—C6D—H6DB | 109.5 |
C11A—C10A—C9A | 119.51 (15) | H6DA—C6D—H6DC | 109.5 |
C11A—C10A—H10A | 120.2 | H6DB—C6D—H6DC | 109.5 |
C9A—C10A—H10A | 120.2 | C7—N3—C8 | 122.68 (19) |
O4A—C11A—C12A | 117.60 (15) | C7—N3—C9 | 120.5 (2) |
O4A—C11A—C10A | 122.16 (15) | C8—N3—C9 | 116.4 (2) |
C12A—C11A—C10A | 120.23 (15) | O3—C7—N3 | 126.36 (19) |
C11A—C12A—C13A | 119.51 (14) | O3—C7—H7 | 116.8 |
C11A—C12A—H12A | 120.2 | N3—C7—H7 | 116.8 |
C13A—C12A—H12A | 120.2 | C1—N1—C3 | 120.86 (15) |
C12A—C13A—C8A | 121.50 (15) | C1—N1—C2 | 121.32 (14) |
C12A—C13A—H13A | 119.2 | C3—N1—C2 | 117.76 (14) |
C8A—C13A—H13A | 119.2 | C5A—O1A—H1AC | 109.5 |
C2B—C1B—C8B | 110.91 (11) | C6A—O2A—H2AA | 109.5 |
C2B—C1B—C4A | 113.22 (11) | C7A—O3A—H3AB | 109.5 |
C8B—C1B—C4A | 110.42 (11) | C11A—O4A—H4AA | 109.5 |
C2B—C1B—H1BA | 107.3 | C5B—O1B—H1BB | 109.5 |
C8B—C1B—H1BA | 107.3 | C6B—O2B—H2BA | 109.5 |
C4A—C1B—H1BA | 107.3 | C7B—O3B—H3BB | 109.5 |
C3B—C2B—C7B | 117.95 (13) | C11B—O4B—H4BB | 109.5 |
C8A—C1A—C2A—C7A | −161.80 (13) | C4A—C1B—C2B—C3B | −33.95 (17) |
C4Bi—C1A—C2A—C7A | 71.99 (16) | C8B—C1B—C2B—C7B | −83.93 (16) |
C8A—C1A—C2A—C3A | 20.07 (18) | C4A—C1B—C2B—C7B | 151.29 (13) |
C4Bi—C1A—C2A—C3A | −106.15 (14) | C7B—C2B—C3B—C4B | −0.1 (2) |
C7A—C2A—C3A—C4A | 1.1 (2) | C1B—C2B—C3B—C4B | −175.04 (13) |
C1A—C2A—C3A—C4A | 179.23 (12) | C2B—C3B—C4B—C5B | −0.8 (2) |
C2A—C3A—C4A—C5A | −1.9 (2) | C2B—C3B—C4B—C1Ai | 178.35 (12) |
C2A—C3A—C4A—C1B | 175.21 (12) | C3B—C4B—C5B—O1B | 179.51 (13) |
C3A—C4A—C5A—O1A | −179.80 (13) | C1Ai—C4B—C5B—O1B | 0.3 (2) |
C1B—C4A—C5A—O1A | 3.0 (2) | C3B—C4B—C5B—C6B | 1.7 (2) |
C3A—C4A—C5A—C6A | 0.8 (2) | C1Ai—C4B—C5B—C6B | −177.45 (13) |
C1B—C4A—C5A—C6A | −176.43 (13) | O1B—C5B—C6B—O2B | −2.8 (2) |
O1A—C5A—C6A—O2A | 2.0 (2) | C4B—C5B—C6B—O2B | 174.88 (15) |
C4A—C5A—C6A—O2A | −178.65 (14) | O1B—C5B—C6B—C7B | −179.36 (14) |
O1A—C5A—C6A—C7A | −178.21 (14) | C4B—C5B—C6B—C7B | −1.7 (2) |
C4A—C5A—C6A—C7A | 1.2 (2) | C3B—C2B—C7B—O3B | −177.59 (12) |
C3A—C2A—C7A—O3A | −179.41 (12) | C1B—C2B—C7B—O3B | −2.7 (2) |
C1A—C2A—C7A—O3A | 2.4 (2) | C3B—C2B—C7B—C6B | 0.2 (2) |
C3A—C2A—C7A—C6A | 1.0 (2) | C1B—C2B—C7B—C6B | 175.17 (13) |
C1A—C2A—C7A—C6A | −177.21 (13) | O2B—C6B—C7B—O3B | 1.6 (2) |
O2A—C6A—C7A—O3A | −1.8 (2) | C5B—C6B—C7B—O3B | 178.46 (13) |
C5A—C6A—C7A—O3A | 178.30 (13) | O2B—C6B—C7B—C2B | −176.17 (13) |
O2A—C6A—C7A—C2A | 177.73 (13) | C5B—C6B—C7B—C2B | 0.7 (2) |
C5A—C6A—C7A—C2A | −2.1 (2) | C2B—C1B—C8B—C13B | 146.49 (13) |
C2A—C1A—C8A—C9A | −96.49 (16) | C4A—C1B—C8B—C13B | −87.17 (15) |
C4Bi—C1A—C8A—C9A | 28.49 (19) | C2B—C1B—C8B—C9B | −39.95 (18) |
C2A—C1A—C8A—C13A | 79.36 (16) | C4A—C1B—C8B—C9B | 86.39 (16) |
C4Bi—C1A—C8A—C13A | −155.66 (13) | C13B—C8B—C9B—C10B | −0.1 (2) |
C13A—C8A—C9A—C10A | 3.0 (2) | C1B—C8B—C9B—C10B | −173.84 (15) |
C1A—C8A—C9A—C10A | 178.86 (14) | C8B—C9B—C10B—C11B | 0.4 (3) |
C8A—C9A—C10A—C11A | 0.2 (2) | C9B—C10B—C11B—O4B | 178.88 (16) |
C9A—C10A—C11A—O4A | 175.37 (15) | C9B—C10B—C11B—C12B | −0.2 (3) |
C9A—C10A—C11A—C12A | −3.3 (3) | O4B—C11B—C12B—C13B | −179.19 (16) |
O4A—C11A—C12A—C13A | −175.59 (15) | C10B—C11B—C12B—C13B | −0.1 (3) |
C10A—C11A—C12A—C13A | 3.1 (3) | C9B—C8B—C13B—C12B | −0.2 (2) |
C11A—C12A—C13A—C8A | 0.1 (2) | C1B—C8B—C13B—C12B | 173.59 (14) |
C9A—C8A—C13A—C12A | −3.1 (2) | C11B—C12B—C13B—C8B | 0.4 (2) |
C1A—C8A—C13A—C12A | −179.18 (14) | C5—N2—C4—O2 | −2.2 (3) |
C3A—C4A—C1B—C2B | 117.68 (14) | C6—N2—C4—O2 | 177.31 (18) |
C5A—C4A—C1B—C2B | −65.21 (16) | C8—N3—C7—O3 | 8.4 (3) |
C3A—C4A—C1B—C8B | −7.35 (18) | C9—N3—C7—O3 | −179.8 (2) |
C5A—C4A—C1B—C8B | 169.75 (13) | O1—C1—N1—C3 | 174.55 (17) |
C8B—C1B—C2B—C3B | 90.82 (15) | O1—C1—N1—C2 | −2.6 (3) |
Symmetry code: (i) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4B—H4BB···O1ii | 0.84 | 2.10 | 2.923 (2) | 168 |
O3B—H3BB···O3Diii | 0.84 | 1.98 | 2.7545 (17) | 153 |
O3B—H3BB···O3iii | 0.84 | 1.98 | 2.7545 (17) | 153 |
O2B—H2BA···O2D | 0.84 | 1.92 | 2.7561 (17) | 174 |
O2B—H2BA···O2 | 0.84 | 1.92 | 2.7561 (17) | 174 |
O1B—H1BB···O2D | 0.84 | 2.00 | 2.8429 (17) | 176 |
O1B—H1BB···O2 | 0.84 | 2.00 | 2.8429 (17) | 176 |
O4A—H4AA···O2Div | 0.84 | 2.48 | 2.8933 (19) | 111 |
O4A—H4AA···O2iv | 0.84 | 2.48 | 2.8933 (19) | 111 |
O3A—H3AB···O4Bv | 0.84 | 1.99 | 2.7663 (17) | 153 |
O2A—H2AA···O1vi | 0.84 | 1.92 | 2.7484 (19) | 169 |
O1A—H1AC···O1vi | 0.84 | 1.89 | 2.7227 (18) | 172 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) x, y, z−1; (v) x, y+1, z; (vi) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C52H40O16·6C3H7NO |
Mr | 1359.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.6481 (5), 11.5153 (6), 14.3315 (7) |
α, β, γ (°) | 75.748 (1), 78.462 (1), 77.891 (1) |
V (Å3) | 1644.8 (1) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.44 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS in SAINT-Plus; Bruker, 2003) |
Tmin, Tmax | 0.914, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17256, 8127, 7050 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.151, 1.03 |
No. of reflections | 8127 |
No. of parameters | 472 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.30 |
Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SAINT-Plus, SHELXTL (Sheldrick, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O4B—H4BB···O1i | 0.84 | 2.10 | 2.923 (2) | 167.9 |
O3B—H3BB···O3Dii | 0.84 | 1.98 | 2.7545 (17) | 153.0 |
O3B—H3BB···O3ii | 0.84 | 1.98 | 2.7545 (17) | 153.0 |
O2B—H2BA···O2D | 0.84 | 1.92 | 2.7561 (17) | 173.5 |
O2B—H2BA···O2 | 0.84 | 1.92 | 2.7561 (17) | 173.5 |
O1B—H1BB···O2D | 0.84 | 2.00 | 2.8429 (17) | 175.6 |
O1B—H1BB···O2 | 0.84 | 2.00 | 2.8429 (17) | 175.6 |
O4A—H4AA···O2Diii | 0.84 | 2.48 | 2.8933 (19) | 111.4 |
O4A—H4AA···O2iii | 0.84 | 2.48 | 2.8933 (19) | 111.4 |
O3A—H3AB···O4Biv | 0.84 | 1.99 | 2.7663 (17) | 153.1 |
O2A—H2AA···O1v | 0.84 | 1.92 | 2.7484 (19) | 169.1 |
O1A—H1AC···O1v | 0.84 | 1.89 | 2.7227 (18) | 172.4 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) x, y, z−1; (iv) x, y+1, z; (v) x−1, y+1, z. |
Calix-shaped compounds such as pyrogallolarenes have received considerable attention during the last two decades due to their potential use in a number of industrial applications (Asfari et al., 2001). The conformational isomers of pyrogallol[4]arenes are being studied by various investigators (Makeiff & Sherman, 2005, and references therein). Our investigations have shown that aryl-substituted pyrogallol[4]arenes adopt a chair (rctt) conformation (Zambrano et al., 2006; Kass et al., 2006), whereas alkyl substituents lead to the crown (rccc) structure (Dueno et al., 2006). Here, we report the crystal structure of the compound 2,8,14,20-para-hydroxytetraphenylpyrogallol[4]arene as its hexa DMF solvate, (1).
The title compound (1) lies on an inversion center. The molecule exhibits a chair (rctt) conformation, characteristic of pyrogallol[4]arenes with aromatic substituents. In this molecule, the pyrogallol ring (C2A to C7A) is separated from its symmetry inverse ring (C2Avi to C7Ai, symmetry code vi = -x, 1 - y, 1 - z) by a distance of 4.934 (2) Å, based on least squares mean planes of both rings. The other two pyrogallol rings (C2B to C7B and C2Bvi to C7Bvi) show an interplanar distance of 0.340 (2) Å. The dihedral angle between the pyrogallol rings not related by symmetry (C2A to C7A and C2B to C7B) is 83.64 (15)°, which indicates that the chair structure is slightly distorted from an ideal, right-angle chair conformation. Another interesting structural feature of this molecule is the position of the p-hydroxyphenyl substituents which are almost perfectly aligned one on top of the other, as in our previously reported compounds (Zambrano et al., 2006). The centroid to centroid distance of the p-hydroxyphenyl rings (C8A to C13A and C8B to C13B) is 4.168 (2) Å, which suggests that there is no π-π interaction (Figure 1).
The asymmetric part of the unit cell contains three molecules of DMF, which are acting as hydrogen bond acceptors for a number the hydroxyl groups of the pyrogallolarene macrocycle and the OH group from the p-hydroxyphenyl substituents (Table 1). The hydrogen-bond distances are all unexceptional (Cave et al., 2005), and these interactions contribute to the stability and molecular arrangement in the crystal packing (Figure 2).