Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021757/pv2012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021757/pv2012Isup2.hkl |
CCDC reference: 657730
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (Wave) = 0.000 Å
- R factor = 0.051
- wR factor = 0.143
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.753 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.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Asfari et al. (2001); Bruno et al. (2002); Cave et al. (2005); Dueno et al. (2006); Farrugia (1997); Kass et al. (2006); Liu et al. (2005); Makeiff & Sherman (2005); Zambrano et al. (2006).
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 273 K and 2 ml of concentrated HCl was added in one portion. Para-anisaldehyde (2.0 g, 16 mmol) was then added dropwise over a period of ten minutes. The reaction vessel was allowed to warm slowly to room temperature and then maintained at 353 K for 12 h, the red powder that separated was collected by filtration and washed with cold 1:1 ethanol-water until the material was pale pink, and neutral to pH paper. Drying under vacuum at 313 K for 12 h afforded 2.6 g (2.8 mmol) of 2,8,14,20-para-methoxytetra(phenyl)pyrogallol[4]arene, yield, 70% mp 632–633 K. Single crystals suitable for X-ray diffraction analysis were grown from a solution in DMF by vapor diffusion of ether to yield large blocks of colorless crystals.
Hydrogen atoms were treated as riding, with O—H = 0.84, C—H = 0.98 for the methoxy methyl group, C—H = 0.95 for phenyl groups and C—H = 1.00Å for the bridging unit. Uiso(H) = 1.5 Ueq(C/O) was used for the methyl and hydroxyl group hydrogen atoms and 1.2 Ueq(C) for all other H atoms. The methyl as well as the hydroxyl groups were allowed to rotate to best fit the experimental electron density.
Bowl-shaped compounds such as pyrogallolarenes have received considerable attention over the last two decades because of their potential use in a number of technological applications (Asfari et al., 2001). The conformational preferences of pyrogallol[4]arenes are still being studied by various investigators (Makeiff, et al., 2005). Our studies have shown that aryl-substituted pyrogallol[4]arenes adopt a chair (rctt) conformation (Zambrano et al., 2006; Kass et al., 2006), whereas the alkyl substituted analogs adopt the crown (rccc) structure (Dueno et al., 2006). Here, we report the crystal structure of a compound 2,8,14,20-para-methoxytetraphenyl-pyrogallol[4]arene, (I), recrystallized by vapor diffusion of diethyl ether into a solution of (I) in N,N-dimethylformamide.
The molecule possesses a center of inversion, where two pairs of pyrogallol rings are clearly distinguishable from each other. One pair is comprised of pyrogallol rings perfectly coplanar to each other, but with their OH groups pointing in opposite directions (ring C8B—C13B and its symmetry inverse counterpart). In the other pair, the aromatic rings are parallel to each other and separated by a distance of 4.982 (9) Å, calculated via least-squares mean planes of ring C8A—C13A and its symmetry equivalent ring (C8A—C13A, symmetry op.: -x, 1 - y, 1 - z). These two pairs of pyrogallol groups are almost perpendicular to each other, for they exhibit a planes angle of 78.88 (12)°. Another interesting structural feature of this molecule is the positions of the para-methoxyphenyl substituents which are almost perfectly aligned on top of each other, as in our previously reported compounds (Zambrano, et al., 2006). This para-methoxyphenyl substituents, are not parallel with respect to each other, but are slightly bent at an angle of 22.82 (12)°, based on least-squares mean planes of both rings carbon atoms (C1A—C6A and C1B—C6B). The centroid to centroid distance between these para-methoxy rings is 4.282 (9)Å with a centroid-centroid offset of 0.112 (2) Å. This separation suggests that no significant π-π interaction is present between aromatic groups (Liu et al., 2005).
The asymmetric unit of (I) contains three molecules of DMF, which are part of an intricate network of hydrogen bonds with the OH groups of the pyrogallolarene macrocycle as the H donor groups (Table 1). H-bonding is also found between the methoxy-O atom and a pyrogallol-OH group (Figure 2). All H-bond values are consistent with the literature (Cave et al., 2005).
For related literature, see: Asfari et al. (2001); Bruno et al. (2002); Cave et al. (2005); Dueno et al. (2006); Farrugia (1997); Kass et al. (2006); Liu et al. (2005); Makeiff & Sherman (2005); Zambrano et al. (2006).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003b); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2003a); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C56H48O16·6C3H7NO | Z = 1 |
Mr = 1415.52 | F(000) = 752 |
Triclinic, P1 | Dx = 1.357 Mg m−3 |
a = 10.8399 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6307 (7) Å | Cell parameters from 5991 reflections |
c = 15.3585 (9) Å | θ = 2.3–30.5° |
α = 73.480 (1)° | µ = 0.10 mm−1 |
β = 73.554 (1)° | T = 100 K |
γ = 73.003 (1)° | Block, pink |
V = 1732.57 (17) Å3 | 0.44 × 0.39 × 0.25 mm |
Bruker SMART APEX CCD diffractometer | 8578 independent reflections |
Radiation source: fine-focus sealed tube | 7224 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003b) | h = −13→14 |
Tmin = 0.889, Tmax = 0.975 | k = −15→15 |
18068 measured reflections | l = −20→20 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0768P)2 + 0.8303P] where P = (Fo2 + 2Fc2)/3 |
8578 reflections | (Δ/σ)max = 0.001 |
474 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C56H48O16·6C3H7NO | γ = 73.003 (1)° |
Mr = 1415.52 | V = 1732.57 (17) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.8399 (6) Å | Mo Kα radiation |
b = 11.6307 (7) Å | µ = 0.10 mm−1 |
c = 15.3585 (9) Å | T = 100 K |
α = 73.480 (1)° | 0.44 × 0.39 × 0.25 mm |
β = 73.554 (1)° |
Bruker SMART APEX CCD diffractometer | 8578 independent reflections |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003b) | 7224 reflections with I > 2σ(I) |
Tmin = 0.889, Tmax = 0.975 | Rint = 0.018 |
18068 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.75 e Å−3 |
8578 reflections | Δρmin = −0.48 e Å−3 |
474 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 | ||
C1 | 0.6658 (2) | 0.6549 (2) | 1.01615 (13) | 0.0441 (5) | |
H1 | 0.7124 | 0.6711 | 1.0536 | 0.053* | |
C2 | 0.6637 (3) | 0.5315 (2) | 0.91362 (17) | 0.0663 (8) | |
H2A | 0.5810 | 0.5926 | 0.9063 | 0.099* | |
H2B | 0.6448 | 0.4501 | 0.9426 | 0.099* | |
H2C | 0.7232 | 0.5295 | 0.8524 | 0.099* | |
C3 | 0.8567 (3) | 0.4911 (3) | 0.97997 (19) | 0.0827 (10) | |
H3A | 0.8927 | 0.5254 | 1.0162 | 0.124* | |
H3B | 0.9143 | 0.4923 | 0.9178 | 0.124* | |
H3C | 0.8520 | 0.4060 | 1.0116 | 0.124* | |
C4 | 0.42933 (16) | 1.11176 (14) | 0.19126 (11) | 0.0250 (3) | |
H4 | 0.4498 | 1.1682 | 0.1339 | 0.030* | |
C5 | 0.47278 (18) | 0.90179 (15) | 0.28231 (12) | 0.0310 (3) | |
H5A | 0.4014 | 0.9384 | 0.3289 | 0.047* | |
H5B | 0.5534 | 0.8674 | 0.3067 | 0.047* | |
H5C | 0.4473 | 0.8361 | 0.2681 | 0.047* | |
C6 | 0.59696 (19) | 0.95763 (18) | 0.11855 (13) | 0.0367 (4) | |
H6A | 0.6050 | 1.0292 | 0.0667 | 0.055* | |
H6B | 0.5708 | 0.8965 | 0.0992 | 0.055* | |
H6C | 0.6821 | 0.9211 | 0.1367 | 0.055* | |
C7 | −0.04528 (16) | 0.06013 (14) | 0.13697 (10) | 0.0246 (3) | |
H7 | −0.1108 | 0.0223 | 0.1815 | 0.030* | |
C8 | 0.1655 (2) | 0.1142 (2) | 0.10120 (13) | 0.0458 (5) | |
H8A | 0.1418 | 0.1525 | 0.0407 | 0.069* | |
H8B | 0.2481 | 0.0510 | 0.0933 | 0.069* | |
H8C | 0.1773 | 0.1772 | 0.1271 | 0.069* | |
C9 | 0.08011 (18) | −0.00344 (16) | 0.25792 (11) | 0.0311 (3) | |
H9A | 0.0044 | −0.0390 | 0.2937 | 0.047* | |
H9B | 0.0879 | 0.0567 | 0.2885 | 0.047* | |
H9C | 0.1611 | −0.0691 | 0.2545 | 0.047* | |
C1A | 0.08449 (15) | 0.54655 (13) | 0.73022 (10) | 0.0221 (3) | |
H1A | 0.0029 | 0.5568 | 0.7142 | 0.026* | |
C2A | 0.10938 (15) | 0.64325 (14) | 0.75351 (11) | 0.0253 (3) | |
H2A1 | 0.0452 | 0.7191 | 0.7529 | 0.030* | |
C3A | 0.22786 (15) | 0.62924 (14) | 0.77765 (10) | 0.0244 (3) | |
C4A | 0.32319 (15) | 0.51968 (15) | 0.77624 (11) | 0.0261 (3) | |
H4A | 0.4054 | 0.5103 | 0.7912 | 0.031* | |
C5A | 0.29646 (15) | 0.42339 (14) | 0.75247 (10) | 0.0235 (3) | |
H5A1 | 0.3616 | 0.3483 | 0.7517 | 0.028* | |
C6A | 0.17776 (14) | 0.43408 (13) | 0.72994 (9) | 0.0184 (3) | |
C7A | 0.15459 (13) | 0.32867 (12) | 0.70084 (9) | 0.0168 (3) | |
H7A | 0.2082 | 0.2503 | 0.7322 | 0.020* | |
C8A | 0.20160 (13) | 0.33775 (12) | 0.59585 (9) | 0.0168 (3) | |
C9A | 0.21157 (14) | 0.23746 (12) | 0.55967 (10) | 0.0188 (3) | |
C10A | 0.24456 (14) | 0.24523 (13) | 0.46370 (10) | 0.0197 (3) | |
C11A | 0.27271 (14) | 0.35332 (13) | 0.40240 (9) | 0.0189 (3) | |
C12A | 0.26516 (13) | 0.45511 (12) | 0.43692 (9) | 0.0167 (3) | |
C13A | 0.22852 (13) | 0.44541 (12) | 0.53301 (9) | 0.0167 (3) | |
H13A | 0.2216 | 0.5147 | 0.5566 | 0.020* | |
C14A | 0.34920 (19) | 0.70947 (19) | 0.84427 (14) | 0.0371 (4) | |
H14A | 0.3467 | 0.6388 | 0.8974 | 0.056* | |
H14B | 0.3425 | 0.7832 | 0.8658 | 0.056* | |
H14C | 0.4326 | 0.6930 | 0.7987 | 0.056* | |
C1B | 0.19028 (14) | 0.75328 (13) | 0.44920 (10) | 0.0209 (3) | |
H1B | 0.1108 | 0.7616 | 0.4309 | 0.025* | |
C2B | 0.19295 (15) | 0.82921 (13) | 0.50364 (10) | 0.0227 (3) | |
H2B1 | 0.1157 | 0.8890 | 0.5222 | 0.027* | |
C3B | 0.30867 (15) | 0.81782 (13) | 0.53097 (10) | 0.0212 (3) | |
C4B | 0.42235 (15) | 0.73175 (13) | 0.50256 (10) | 0.0213 (3) | |
H4B | 0.5020 | 0.7244 | 0.5203 | 0.026* | |
C5B | 0.41803 (14) | 0.65622 (13) | 0.44765 (10) | 0.0193 (3) | |
H5B1 | 0.4958 | 0.5976 | 0.4281 | 0.023* | |
C6B | 0.30300 (14) | 0.66457 (12) | 0.42082 (9) | 0.0174 (3) | |
C7B | 0.29994 (13) | 0.57199 (12) | 0.36881 (9) | 0.0164 (3) | |
H7B | 0.3914 | 0.5472 | 0.3314 | 0.020* | |
C8B | 0.20893 (14) | 0.62977 (12) | 0.30071 (9) | 0.0175 (3) | |
C9B | 0.25441 (14) | 0.69388 (13) | 0.21136 (9) | 0.0190 (3) | |
C10B | 0.16993 (14) | 0.74998 (13) | 0.14914 (9) | 0.0203 (3) | |
C11B | 0.03791 (14) | 0.74173 (13) | 0.17682 (9) | 0.0196 (3) | |
C12B | −0.01042 (13) | 0.67990 (12) | 0.26735 (9) | 0.0177 (3) | |
C13B | 0.07631 (13) | 0.62514 (12) | 0.32698 (9) | 0.0174 (3) | |
H13B | 0.0437 | 0.5828 | 0.3882 | 0.021* | |
C14B | 0.41800 (18) | 0.88299 (17) | 0.61660 (14) | 0.0351 (4) | |
H14D | 0.4500 | 0.7970 | 0.6468 | 0.053* | |
H14E | 0.3988 | 0.9356 | 0.6608 | 0.053* | |
H14F | 0.4859 | 0.9083 | 0.5625 | 0.053* | |
N1 | 0.72534 (19) | 0.56446 (18) | 0.97160 (11) | 0.0471 (4) | |
N2 | 0.49696 (13) | 0.99649 (12) | 0.19751 (9) | 0.0254 (3) | |
N3 | 0.06071 (13) | 0.05763 (12) | 0.16428 (9) | 0.0256 (3) | |
O1 | 0.55477 (17) | 0.71894 (15) | 1.01234 (10) | 0.0533 (4) | |
O2 | 0.34118 (13) | 1.15300 (11) | 0.25381 (8) | 0.0315 (3) | |
O3 | −0.06606 (12) | 0.10807 (11) | 0.05755 (8) | 0.0312 (3) | |
O1A | 0.24155 (12) | 0.72893 (11) | 0.80213 (9) | 0.0330 (3) | |
O2A | 0.18662 (11) | 0.12992 (9) | 0.61961 (7) | 0.0235 (2) | |
H2A2 | 0.2089 | 0.0738 | 0.5900 | 0.035* | |
O3A | 0.24647 (13) | 0.14031 (10) | 0.43813 (8) | 0.0291 (3) | |
H3A1 | 0.2755 | 0.1483 | 0.3804 | 0.044* | |
O4A | 0.31128 (12) | 0.36441 (10) | 0.30769 (7) | 0.0251 (2) | |
H4A1 | 0.3096 | 0.2997 | 0.2945 | 0.038* | |
O1B | 0.30071 (11) | 0.89459 (10) | 0.58718 (8) | 0.0264 (2) | |
O2B | 0.38426 (10) | 0.70251 (11) | 0.18480 (7) | 0.0253 (2) | |
H2B2 | 0.4065 | 0.7207 | 0.1265 | 0.038* | |
O3B | 0.22783 (11) | 0.81115 (12) | 0.06305 (7) | 0.0305 (3) | |
H3B1 | 0.1726 | 0.8390 | 0.0289 | 0.046* | |
O4B | −0.05048 (11) | 0.79371 (11) | 0.11931 (7) | 0.0266 (2) | |
H4B1 | −0.0101 | 0.8211 | 0.0654 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0588 (13) | 0.0467 (11) | 0.0240 (8) | −0.0203 (10) | −0.0031 (8) | −0.0009 (8) |
C2 | 0.107 (2) | 0.0506 (14) | 0.0404 (12) | −0.0024 (14) | −0.0303 (13) | −0.0113 (10) |
C3 | 0.0444 (14) | 0.117 (3) | 0.0488 (14) | 0.0006 (15) | 0.0047 (11) | 0.0060 (15) |
C4 | 0.0340 (8) | 0.0234 (7) | 0.0213 (7) | −0.0108 (6) | −0.0083 (6) | −0.0042 (5) |
C5 | 0.0343 (9) | 0.0232 (8) | 0.0297 (8) | −0.0071 (6) | −0.0024 (7) | −0.0009 (6) |
C6 | 0.0358 (9) | 0.0375 (9) | 0.0307 (9) | −0.0056 (7) | 0.0024 (7) | −0.0108 (7) |
C7 | 0.0279 (7) | 0.0250 (7) | 0.0201 (7) | −0.0068 (6) | −0.0046 (6) | −0.0035 (6) |
C8 | 0.0402 (10) | 0.0713 (14) | 0.0295 (9) | −0.0312 (10) | −0.0048 (8) | −0.0003 (9) |
C9 | 0.0398 (9) | 0.0301 (8) | 0.0246 (7) | −0.0091 (7) | −0.0144 (7) | 0.0003 (6) |
C1A | 0.0214 (7) | 0.0223 (7) | 0.0233 (7) | −0.0036 (5) | −0.0063 (5) | −0.0063 (5) |
C2A | 0.0257 (7) | 0.0213 (7) | 0.0288 (7) | −0.0029 (6) | −0.0051 (6) | −0.0086 (6) |
C3A | 0.0276 (7) | 0.0258 (7) | 0.0229 (7) | −0.0104 (6) | −0.0025 (6) | −0.0087 (6) |
C4A | 0.0229 (7) | 0.0309 (8) | 0.0280 (7) | −0.0067 (6) | −0.0077 (6) | −0.0092 (6) |
C5A | 0.0229 (7) | 0.0238 (7) | 0.0243 (7) | −0.0023 (6) | −0.0070 (6) | −0.0075 (6) |
C6A | 0.0214 (6) | 0.0198 (6) | 0.0142 (6) | −0.0057 (5) | −0.0029 (5) | −0.0041 (5) |
C7A | 0.0190 (6) | 0.0158 (6) | 0.0153 (6) | −0.0034 (5) | −0.0048 (5) | −0.0024 (5) |
C8A | 0.0166 (6) | 0.0168 (6) | 0.0167 (6) | −0.0028 (5) | −0.0042 (5) | −0.0039 (5) |
C9A | 0.0194 (6) | 0.0163 (6) | 0.0195 (6) | −0.0039 (5) | −0.0041 (5) | −0.0023 (5) |
C10A | 0.0235 (7) | 0.0162 (6) | 0.0214 (7) | −0.0046 (5) | −0.0059 (5) | −0.0063 (5) |
C11A | 0.0212 (6) | 0.0188 (6) | 0.0169 (6) | −0.0039 (5) | −0.0044 (5) | −0.0047 (5) |
C12A | 0.0167 (6) | 0.0156 (6) | 0.0177 (6) | −0.0028 (5) | −0.0049 (5) | −0.0032 (5) |
C13A | 0.0164 (6) | 0.0167 (6) | 0.0173 (6) | −0.0032 (5) | −0.0047 (5) | −0.0039 (5) |
C14A | 0.0369 (9) | 0.0446 (10) | 0.0408 (10) | −0.0185 (8) | −0.0078 (8) | −0.0177 (8) |
C1B | 0.0210 (7) | 0.0203 (7) | 0.0219 (7) | −0.0037 (5) | −0.0075 (5) | −0.0037 (5) |
C2B | 0.0242 (7) | 0.0189 (7) | 0.0248 (7) | −0.0012 (5) | −0.0073 (6) | −0.0061 (5) |
C3B | 0.0274 (7) | 0.0169 (6) | 0.0208 (6) | −0.0054 (5) | −0.0077 (5) | −0.0040 (5) |
C4B | 0.0222 (7) | 0.0201 (7) | 0.0235 (7) | −0.0057 (5) | −0.0086 (5) | −0.0035 (5) |
C5B | 0.0197 (6) | 0.0167 (6) | 0.0206 (6) | −0.0041 (5) | −0.0045 (5) | −0.0028 (5) |
C6B | 0.0215 (6) | 0.0150 (6) | 0.0157 (6) | −0.0060 (5) | −0.0044 (5) | −0.0012 (5) |
C7B | 0.0175 (6) | 0.0166 (6) | 0.0150 (6) | −0.0046 (5) | −0.0036 (5) | −0.0026 (5) |
C8B | 0.0206 (6) | 0.0163 (6) | 0.0161 (6) | −0.0042 (5) | −0.0051 (5) | −0.0031 (5) |
C9B | 0.0195 (6) | 0.0203 (6) | 0.0177 (6) | −0.0064 (5) | −0.0034 (5) | −0.0037 (5) |
C10B | 0.0244 (7) | 0.0207 (6) | 0.0148 (6) | −0.0076 (5) | −0.0037 (5) | −0.0001 (5) |
C11B | 0.0224 (7) | 0.0198 (6) | 0.0161 (6) | −0.0036 (5) | −0.0063 (5) | −0.0024 (5) |
C12B | 0.0196 (6) | 0.0171 (6) | 0.0165 (6) | −0.0044 (5) | −0.0037 (5) | −0.0040 (5) |
C13B | 0.0206 (6) | 0.0160 (6) | 0.0157 (6) | −0.0049 (5) | −0.0042 (5) | −0.0025 (5) |
C14B | 0.0370 (9) | 0.0328 (9) | 0.0455 (10) | −0.0007 (7) | −0.0216 (8) | −0.0190 (8) |
N1 | 0.0497 (10) | 0.0558 (11) | 0.0290 (8) | −0.0091 (8) | −0.0030 (7) | −0.0075 (7) |
N2 | 0.0300 (7) | 0.0242 (6) | 0.0215 (6) | −0.0087 (5) | −0.0025 (5) | −0.0044 (5) |
N3 | 0.0282 (7) | 0.0284 (7) | 0.0192 (6) | −0.0086 (5) | −0.0058 (5) | −0.0009 (5) |
O1 | 0.0629 (10) | 0.0495 (9) | 0.0272 (7) | −0.0027 (7) | 0.0004 (6) | 0.0019 (6) |
O2 | 0.0435 (7) | 0.0260 (6) | 0.0260 (6) | −0.0065 (5) | −0.0055 (5) | −0.0107 (5) |
O3 | 0.0335 (6) | 0.0380 (7) | 0.0199 (5) | −0.0065 (5) | −0.0083 (5) | −0.0023 (5) |
O1A | 0.0337 (6) | 0.0313 (6) | 0.0425 (7) | −0.0105 (5) | −0.0085 (5) | −0.0176 (5) |
O2A | 0.0331 (6) | 0.0155 (5) | 0.0211 (5) | −0.0083 (4) | −0.0021 (4) | −0.0039 (4) |
O3A | 0.0482 (7) | 0.0205 (5) | 0.0219 (5) | −0.0136 (5) | −0.0038 (5) | −0.0076 (4) |
O4A | 0.0392 (6) | 0.0203 (5) | 0.0163 (5) | −0.0078 (5) | −0.0037 (4) | −0.0060 (4) |
O1B | 0.0314 (6) | 0.0217 (5) | 0.0310 (6) | −0.0013 (4) | −0.0142 (5) | −0.0110 (4) |
O2B | 0.0210 (5) | 0.0356 (6) | 0.0181 (5) | −0.0118 (4) | −0.0031 (4) | 0.0002 (4) |
O3B | 0.0273 (6) | 0.0433 (7) | 0.0171 (5) | −0.0147 (5) | −0.0058 (4) | 0.0068 (5) |
O4B | 0.0242 (5) | 0.0346 (6) | 0.0181 (5) | −0.0085 (5) | −0.0081 (4) | 0.0040 (4) |
C1—O1 | 1.224 (3) | C8A—C13A | 1.3968 (18) |
C1—N1 | 1.324 (3) | C9A—O2A | 1.3736 (16) |
C1—H1 | 0.9500 | C9A—C10A | 1.3976 (19) |
C2—N1 | 1.438 (3) | C10A—O3A | 1.3773 (16) |
C2—H2A | 0.9800 | C10A—C11A | 1.3959 (19) |
C2—H2B | 0.9800 | C11A—O4A | 1.3740 (16) |
C2—H2C | 0.9800 | C11A—C12A | 1.4019 (18) |
C3—N1 | 1.451 (3) | C12A—C13A | 1.3957 (18) |
C3—H3A | 0.9800 | C12A—C7B | 1.5336 (18) |
C3—H3B | 0.9800 | C13A—H13A | 0.9500 |
C3—H3C | 0.9800 | C14A—O1A | 1.422 (2) |
C4—O2 | 1.241 (2) | C14A—H14A | 0.9800 |
C4—N2 | 1.318 (2) | C14A—H14B | 0.9800 |
C4—H4 | 0.9500 | C14A—H14C | 0.9800 |
C5—N2 | 1.462 (2) | C1B—C2B | 1.389 (2) |
C5—H5A | 0.9800 | C1B—C6B | 1.402 (2) |
C5—H5B | 0.9800 | C1B—H1B | 0.9500 |
C5—H5C | 0.9800 | C2B—C3B | 1.392 (2) |
C6—N2 | 1.460 (2) | C2B—H2B1 | 0.9500 |
C6—H6A | 0.9800 | C3B—O1B | 1.3788 (17) |
C6—H6B | 0.9800 | C3B—C4B | 1.391 (2) |
C6—H6C | 0.9800 | C4B—C5B | 1.397 (2) |
C7—O3 | 1.2429 (19) | C4B—H4B | 0.9500 |
C7—N3 | 1.320 (2) | C5B—C6B | 1.3897 (19) |
C7—H7 | 0.9500 | C5B—H5B1 | 0.9500 |
C8—N3 | 1.453 (2) | C6B—C7B | 1.5243 (18) |
C8—H8A | 0.9800 | C7B—C8B | 1.5218 (18) |
C8—H8B | 0.9800 | C7B—H7B | 1.0000 |
C8—H8C | 0.9800 | C8B—C9B | 1.3899 (19) |
C9—N3 | 1.456 (2) | C8B—C13B | 1.3916 (19) |
C9—H9A | 0.9800 | C9B—O2B | 1.3755 (17) |
C9—H9B | 0.9800 | C9B—C10B | 1.403 (2) |
C9—H9C | 0.9800 | C10B—O3B | 1.3801 (16) |
C1A—C2A | 1.388 (2) | C10B—C11B | 1.397 (2) |
C1A—C6A | 1.400 (2) | C11B—O4B | 1.3786 (17) |
C1A—H1A | 0.9500 | C11B—C12B | 1.4015 (19) |
C2A—C3A | 1.388 (2) | C12B—C13B | 1.3907 (19) |
C2A—H2A1 | 0.9500 | C12B—C7Ai | 1.5237 (19) |
C3A—O1A | 1.3740 (18) | C13B—H13B | 0.9500 |
C3A—C4A | 1.388 (2) | C14B—O1B | 1.4244 (19) |
C4A—C5A | 1.398 (2) | C14B—H14D | 0.9800 |
C4A—H4A | 0.9500 | C14B—H14E | 0.9800 |
C5A—C6A | 1.387 (2) | C14B—H14F | 0.9800 |
C5A—H5A1 | 0.9500 | O2A—H2A2 | 0.8400 |
C6A—C7A | 1.5235 (18) | O3A—H3A1 | 0.8400 |
C7A—C12Bi | 1.5237 (19) | O4A—H4A1 | 0.8400 |
C7A—C8A | 1.5298 (18) | O2B—H2B2 | 0.8400 |
C7A—H7A | 1.0000 | O3B—H3B1 | 0.8400 |
C8A—C9A | 1.3936 (19) | O4B—H4B1 | 0.8400 |
O1—C1—N1 | 124.4 (2) | O4A—C11A—C12A | 117.35 (12) |
O1—C1—H1 | 117.8 | C10A—C11A—C12A | 120.05 (12) |
N1—C1—H1 | 117.8 | C13A—C12A—C11A | 118.47 (12) |
N1—C2—H2A | 109.5 | C13A—C12A—C7B | 122.12 (12) |
N1—C2—H2B | 109.5 | C11A—C12A—C7B | 119.40 (12) |
H2A—C2—H2B | 109.5 | C12A—C13A—C8A | 122.58 (12) |
N1—C2—H2C | 109.5 | C12A—C13A—H13A | 118.7 |
H2A—C2—H2C | 109.5 | C8A—C13A—H13A | 118.7 |
H2B—C2—H2C | 109.5 | O1A—C14A—H14A | 109.5 |
N1—C3—H3A | 109.5 | O1A—C14A—H14B | 109.5 |
N1—C3—H3B | 109.5 | H14A—C14A—H14B | 109.5 |
H3A—C3—H3B | 109.5 | O1A—C14A—H14C | 109.5 |
N1—C3—H3C | 109.5 | H14A—C14A—H14C | 109.5 |
H3A—C3—H3C | 109.5 | H14B—C14A—H14C | 109.5 |
H3B—C3—H3C | 109.5 | C2B—C1B—C6B | 121.00 (13) |
O2—C4—N2 | 125.68 (15) | C2B—C1B—H1B | 119.5 |
O2—C4—H4 | 117.2 | C6B—C1B—H1B | 119.5 |
N2—C4—H4 | 117.2 | C1B—C2B—C3B | 120.04 (13) |
N2—C5—H5A | 109.5 | C1B—C2B—H2B1 | 120.0 |
N2—C5—H5B | 109.5 | C3B—C2B—H2B1 | 120.0 |
H5A—C5—H5B | 109.5 | O1B—C3B—C4B | 124.09 (13) |
N2—C5—H5C | 109.5 | O1B—C3B—C2B | 115.86 (13) |
H5A—C5—H5C | 109.5 | C4B—C3B—C2B | 120.04 (13) |
H5B—C5—H5C | 109.5 | C3B—C4B—C5B | 119.19 (13) |
N2—C6—H6A | 109.5 | C3B—C4B—H4B | 120.4 |
N2—C6—H6B | 109.5 | C5B—C4B—H4B | 120.4 |
H6A—C6—H6B | 109.5 | C6B—C5B—C4B | 121.76 (13) |
N2—C6—H6C | 109.5 | C6B—C5B—H5B1 | 119.1 |
H6A—C6—H6C | 109.5 | C4B—C5B—H5B1 | 119.1 |
H6B—C6—H6C | 109.5 | C5B—C6B—C1B | 117.96 (12) |
O3—C7—N3 | 125.13 (15) | C5B—C6B—C7B | 119.63 (12) |
O3—C7—H7 | 117.4 | C1B—C6B—C7B | 122.23 (12) |
N3—C7—H7 | 117.4 | C8B—C7B—C6B | 111.47 (11) |
N3—C8—H8A | 109.5 | C8B—C7B—C12A | 112.53 (11) |
N3—C8—H8B | 109.5 | C6B—C7B—C12A | 110.97 (11) |
H8A—C8—H8B | 109.5 | C8B—C7B—H7B | 107.2 |
N3—C8—H8C | 109.5 | C6B—C7B—H7B | 107.2 |
H8A—C8—H8C | 109.5 | C12A—C7B—H7B | 107.2 |
H8B—C8—H8C | 109.5 | C9B—C8B—C13B | 117.81 (12) |
N3—C9—H9A | 109.5 | C9B—C8B—C7B | 120.86 (12) |
N3—C9—H9B | 109.5 | C13B—C8B—C7B | 121.27 (12) |
H9A—C9—H9B | 109.5 | O2B—C9B—C8B | 118.78 (12) |
N3—C9—H9C | 109.5 | O2B—C9B—C10B | 120.17 (12) |
H9A—C9—H9C | 109.5 | C8B—C9B—C10B | 121.04 (13) |
H9B—C9—H9C | 109.5 | O3B—C10B—C11B | 125.18 (13) |
C2A—C1A—C6A | 121.08 (14) | O3B—C10B—C9B | 114.94 (13) |
C2A—C1A—H1A | 119.5 | C11B—C10B—C9B | 119.88 (12) |
C6A—C1A—H1A | 119.5 | O4B—C11B—C10B | 123.10 (12) |
C3A—C2A—C1A | 120.07 (14) | O4B—C11B—C12B | 117.05 (12) |
C3A—C2A—H2A1 | 120.0 | C10B—C11B—C12B | 119.85 (13) |
C1A—C2A—H2A1 | 120.0 | C13B—C12B—C11B | 118.63 (13) |
O1A—C3A—C4A | 124.20 (14) | C13B—C12B—C7Ai | 120.78 (12) |
O1A—C3A—C2A | 115.68 (14) | C11B—C12B—C7Ai | 120.58 (12) |
C4A—C3A—C2A | 120.12 (14) | C12B—C13B—C8B | 122.76 (13) |
C3A—C4A—C5A | 118.97 (14) | C12B—C13B—H13B | 118.6 |
C3A—C4A—H4A | 120.5 | C8B—C13B—H13B | 118.6 |
C5A—C4A—H4A | 120.5 | O1B—C14B—H14D | 109.5 |
C6A—C5A—C4A | 122.06 (14) | O1B—C14B—H14E | 109.5 |
C6A—C5A—H5A1 | 119.0 | H14D—C14B—H14E | 109.5 |
C4A—C5A—H5A1 | 119.0 | O1B—C14B—H14F | 109.5 |
C5A—C6A—C1A | 117.67 (13) | H14D—C14B—H14F | 109.5 |
C5A—C6A—C7A | 120.40 (12) | H14E—C14B—H14F | 109.5 |
C1A—C6A—C7A | 121.84 (12) | C1—N1—C2 | 122.4 (2) |
C6A—C7A—C12Bi | 111.99 (11) | C1—N1—C3 | 121.5 (2) |
C6A—C7A—C8A | 111.96 (11) | C2—N1—C3 | 116.0 (2) |
C12Bi—C7A—C8A | 110.42 (11) | C4—N2—C6 | 120.99 (14) |
C6A—C7A—H7A | 107.4 | C4—N2—C5 | 121.72 (13) |
C12Bi—C7A—H7A | 107.4 | C6—N2—C5 | 117.27 (14) |
C8A—C7A—H7A | 107.4 | C7—N3—C8 | 121.29 (14) |
C9A—C8A—C13A | 117.73 (12) | C7—N3—C9 | 122.09 (14) |
C9A—C8A—C7A | 119.38 (12) | C8—N3—C9 | 116.61 (14) |
C13A—C8A—C7A | 122.79 (12) | C3A—O1A—C14A | 116.79 (13) |
O2A—C9A—C8A | 119.20 (12) | C9A—O2A—H2A2 | 109.5 |
O2A—C9A—C10A | 119.68 (12) | C10A—O3A—H3A1 | 109.5 |
C8A—C9A—C10A | 121.11 (12) | C11A—O4A—H4A1 | 109.5 |
O3A—C10A—C11A | 125.35 (13) | C3B—O1B—C14B | 116.51 (12) |
O3A—C10A—C9A | 114.62 (12) | C9B—O2B—H2B2 | 109.5 |
C11A—C10A—C9A | 120.02 (12) | C10B—O3B—H3B1 | 109.5 |
O4A—C11A—C10A | 122.58 (12) | C11B—O4B—H4B1 | 109.5 |
C6A—C1A—C2A—C3A | −0.4 (2) | C4B—C5B—C6B—C7B | −174.18 (12) |
C1A—C2A—C3A—O1A | −178.20 (14) | C2B—C1B—C6B—C5B | −1.0 (2) |
C1A—C2A—C3A—C4A | 1.7 (2) | C2B—C1B—C6B—C7B | 174.18 (13) |
O1A—C3A—C4A—C5A | 178.30 (14) | C5B—C6B—C7B—C8B | −147.78 (12) |
C2A—C3A—C4A—C5A | −1.6 (2) | C1B—C6B—C7B—C8B | 37.16 (17) |
C3A—C4A—C5A—C6A | 0.2 (2) | C5B—C6B—C7B—C12A | 85.95 (15) |
C4A—C5A—C6A—C1A | 1.0 (2) | C1B—C6B—C7B—C12A | −89.11 (15) |
C4A—C5A—C6A—C7A | 177.66 (13) | C13A—C12A—C7B—C8B | −119.55 (14) |
C2A—C1A—C6A—C5A | −0.9 (2) | C11A—C12A—C7B—C8B | 61.78 (16) |
C2A—C1A—C6A—C7A | −177.51 (13) | C13A—C12A—C7B—C6B | 6.13 (18) |
C5A—C6A—C7A—C12Bi | 146.61 (13) | C11A—C12A—C7B—C6B | −172.53 (12) |
C1A—C6A—C7A—C12Bi | −36.85 (17) | C6B—C7B—C8B—C9B | 85.55 (15) |
C5A—C6A—C7A—C8A | −88.73 (15) | C12A—C7B—C8B—C9B | −149.04 (13) |
C1A—C6A—C7A—C8A | 87.80 (16) | C6B—C7B—C8B—C13B | −91.47 (15) |
C6A—C7A—C8A—C9A | 167.71 (12) | C12A—C7B—C8B—C13B | 33.94 (17) |
C12Bi—C7A—C8A—C9A | −66.78 (16) | C13B—C8B—C9B—O2B | 178.24 (12) |
C6A—C7A—C8A—C13A | −15.94 (18) | C7B—C8B—C9B—O2B | 1.1 (2) |
C12Bi—C7A—C8A—C13A | 109.57 (14) | C13B—C8B—C9B—C10B | −1.2 (2) |
C13A—C8A—C9A—O2A | 179.57 (12) | C7B—C8B—C9B—C10B | −178.36 (13) |
C7A—C8A—C9A—O2A | −3.90 (19) | O2B—C9B—C10B—O3B | 0.1 (2) |
C13A—C8A—C9A—C10A | −1.4 (2) | C8B—C9B—C10B—O3B | 179.62 (13) |
C7A—C8A—C9A—C10A | 175.16 (13) | O2B—C9B—C10B—C11B | −179.47 (13) |
O2A—C9A—C10A—O3A | 1.1 (2) | C8B—C9B—C10B—C11B | 0.0 (2) |
C8A—C9A—C10A—O3A | −177.96 (13) | O3B—C10B—C11B—O4B | 0.9 (2) |
O2A—C9A—C10A—C11A | −178.68 (13) | C9B—C10B—C11B—O4B | −179.53 (13) |
C8A—C9A—C10A—C11A | 2.3 (2) | O3B—C10B—C11B—C12B | −178.10 (14) |
O3A—C10A—C11A—O4A | −2.7 (2) | C9B—C10B—C11B—C12B | 1.5 (2) |
C9A—C10A—C11A—O4A | 177.09 (13) | O4B—C11B—C12B—C13B | 179.29 (12) |
O3A—C10A—C11A—C12A | 178.87 (13) | C10B—C11B—C12B—C13B | −1.7 (2) |
C9A—C10A—C11A—C12A | −1.4 (2) | O4B—C11B—C12B—C7Ai | 0.19 (19) |
O4A—C11A—C12A—C13A | −178.86 (12) | C10B—C11B—C12B—C7Ai | 179.25 (12) |
C10A—C11A—C12A—C13A | −0.3 (2) | C11B—C12B—C13B—C8B | 0.4 (2) |
O4A—C11A—C12A—C7B | −0.15 (19) | C7Ai—C12B—C13B—C8B | 179.48 (12) |
C10A—C11A—C12A—C7B | 178.40 (12) | C9B—C8B—C13B—C12B | 1.1 (2) |
C11A—C12A—C13A—C8A | 1.2 (2) | C7B—C8B—C13B—C12B | 178.16 (12) |
C7B—C12A—C13A—C8A | −177.46 (12) | O1—C1—N1—C2 | −0.4 (3) |
C9A—C8A—C13A—C12A | −0.4 (2) | O1—C1—N1—C3 | −179.3 (2) |
C7A—C8A—C13A—C12A | −176.78 (12) | O2—C4—N2—C6 | 178.74 (16) |
C6B—C1B—C2B—C3B | −0.1 (2) | O2—C4—N2—C5 | 0.5 (3) |
C1B—C2B—C3B—O1B | −178.13 (13) | O3—C7—N3—C8 | 0.6 (3) |
C1B—C2B—C3B—C4B | 1.0 (2) | O3—C7—N3—C9 | −178.20 (16) |
O1B—C3B—C4B—C5B | 178.18 (13) | C4A—C3A—O1A—C14A | −11.8 (2) |
C2B—C3B—C4B—C5B | −0.9 (2) | C2A—C3A—O1A—C14A | 168.08 (15) |
C3B—C4B—C5B—C6B | −0.2 (2) | C4B—C3B—O1B—C14B | 0.2 (2) |
C4B—C5B—C6B—C1B | 1.1 (2) | C2B—C3B—O1B—C14B | 179.30 (14) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4B—H4B1···O3B | 0.84 | 2.54 | 2.9446 (16) | 111 |
O4B—H4B1···O3ii | 0.84 | 1.89 | 2.7231 (15) | 175 |
O3B—H3B1···O4B | 0.84 | 2.55 | 2.9446 (16) | 110 |
O3B—H3B1···O3ii | 0.84 | 1.86 | 2.6971 (16) | 173 |
O2B—H2B2···O3B | 0.84 | 2.26 | 2.6773 (15) | 111 |
O2B—H2B2···O1iii | 0.84 | 2.02 | 2.7595 (18) | 147 |
O4A—H4A1···O3A | 0.84 | 2.52 | 2.9334 (15) | 112 |
O4A—H4A1···O2iv | 0.84 | 1.89 | 2.7158 (15) | 169 |
O3A—H3A1···O4A | 0.84 | 2.54 | 2.9334 (15) | 110 |
O3A—H3A1···O2iv | 0.84 | 1.86 | 2.7010 (16) | 176 |
O2A—H2A2···O3A | 0.84 | 2.20 | 2.6523 (15) | 114 |
O2A—H2A2···O1Biv | 0.84 | 2.04 | 2.7779 (15) | 147 |
Symmetry codes: (ii) −x, −y+1, −z; (iii) x, y, z−1; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C56H48O16·6C3H7NO |
Mr | 1415.52 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.8399 (6), 11.6307 (7), 15.3585 (9) |
α, β, γ (°) | 73.480 (1), 73.554 (1), 73.003 (1) |
V (Å3) | 1732.57 (17) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.44 × 0.39 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS in SAINT-Plus; Bruker, 2003b) |
Tmin, Tmax | 0.889, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18068, 8578, 7224 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.143, 1.03 |
No. of reflections | 8578 |
No. of parameters | 474 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.75, −0.48 |
Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003b), SAINT-Plus, SHELXTL (Bruker, 2003a), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O4B—H4B1···O3B | 0.84 | 2.54 | 2.9446 (16) | 110.9 |
O4B—H4B1···O3i | 0.84 | 1.89 | 2.7231 (15) | 174.9 |
O3B—H3B1···O4B | 0.84 | 2.55 | 2.9446 (16) | 110.3 |
O3B—H3B1···O3i | 0.84 | 1.86 | 2.6971 (16) | 173.1 |
O2B—H2B2···O3B | 0.84 | 2.26 | 2.6773 (15) | 111.0 |
O2B—H2B2···O1ii | 0.84 | 2.02 | 2.7595 (18) | 147.3 |
O4A—H4A1···O3A | 0.84 | 2.52 | 2.9334 (15) | 111.8 |
O4A—H4A1···O2iii | 0.84 | 1.89 | 2.7158 (15) | 168.7 |
O3A—H3A1···O4A | 0.84 | 2.54 | 2.9334 (15) | 110.0 |
O3A—H3A1···O2iii | 0.84 | 1.86 | 2.7010 (16) | 175.5 |
O2A—H2A2···O3A | 0.84 | 2.20 | 2.6523 (15) | 114.0 |
O2A—H2A2···O1Biii | 0.84 | 2.04 | 2.7779 (15) | 146.7 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y, z−1; (iii) x, y−1, z. |
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Bowl-shaped compounds such as pyrogallolarenes have received considerable attention over the last two decades because of their potential use in a number of technological applications (Asfari et al., 2001). The conformational preferences of pyrogallol[4]arenes are still being studied by various investigators (Makeiff, et al., 2005). Our studies have shown that aryl-substituted pyrogallol[4]arenes adopt a chair (rctt) conformation (Zambrano et al., 2006; Kass et al., 2006), whereas the alkyl substituted analogs adopt the crown (rccc) structure (Dueno et al., 2006). Here, we report the crystal structure of a compound 2,8,14,20-para-methoxytetraphenyl-pyrogallol[4]arene, (I), recrystallized by vapor diffusion of diethyl ether into a solution of (I) in N,N-dimethylformamide.
The molecule possesses a center of inversion, where two pairs of pyrogallol rings are clearly distinguishable from each other. One pair is comprised of pyrogallol rings perfectly coplanar to each other, but with their OH groups pointing in opposite directions (ring C8B—C13B and its symmetry inverse counterpart). In the other pair, the aromatic rings are parallel to each other and separated by a distance of 4.982 (9) Å, calculated via least-squares mean planes of ring C8A—C13A and its symmetry equivalent ring (C8A—C13A, symmetry op.: -x, 1 - y, 1 - z). These two pairs of pyrogallol groups are almost perpendicular to each other, for they exhibit a planes angle of 78.88 (12)°. Another interesting structural feature of this molecule is the positions of the para-methoxyphenyl substituents which are almost perfectly aligned on top of each other, as in our previously reported compounds (Zambrano, et al., 2006). This para-methoxyphenyl substituents, are not parallel with respect to each other, but are slightly bent at an angle of 22.82 (12)°, based on least-squares mean planes of both rings carbon atoms (C1A—C6A and C1B—C6B). The centroid to centroid distance between these para-methoxy rings is 4.282 (9)Å with a centroid-centroid offset of 0.112 (2) Å. This separation suggests that no significant π-π interaction is present between aromatic groups (Liu et al., 2005).
The asymmetric unit of (I) contains three molecules of DMF, which are part of an intricate network of hydrogen bonds with the OH groups of the pyrogallolarene macrocycle as the H donor groups (Table 1). H-bonding is also found between the methoxy-O atom and a pyrogallol-OH group (Figure 2). All H-bond values are consistent with the literature (Cave et al., 2005).