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The title compound, C56H48O16·6C3H7NO, adopts a macrocyclic chair conformation in the solid state. The asymmetric unit contains one half of the mol­ecule, which lies on a crystallographic inversion center, and three mol­ecules of dimethyl­formamide. The crystal structure is stabilized by extensive hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021757/pv2012sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021757/pv2012Isup2.hkl
Contains datablock I

CCDC reference: 657730

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. An ORTEP view of (I) (Farrugia, 1997); displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Mercury packing diagram (Bruno et al., 2002) of (I), viewed down the a axis, dashed lines indicate hydrogen bonds.
2,8,14,20-para-Methoxytetraphenylpyrogallol[4]arene dimethylformamide hexasolvate top
Crystal data top
C56H48O16·6C3H7NOZ = 1
Mr = 1415.52F(000) = 752
Triclinic, P1Dx = 1.357 Mg m3
a = 10.8399 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6307 (7) ÅCell parameters from 5991 reflections
c = 15.3585 (9) Åθ = 2.3–30.5°
α = 73.480 (1)°µ = 0.10 mm1
β = 73.554 (1)°T = 100 K
γ = 73.003 (1)°Block, pink
V = 1732.57 (17) Å30.44 × 0.39 × 0.25 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
8578 independent reflections
Radiation source: fine-focus sealed tube7224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003b)
h = 1314
Tmin = 0.889, Tmax = 0.975k = 1515
18068 measured reflectionsl = 2020
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-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 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
C56H48O16·6C3H7NOγ = 73.003 (1)°
Mr = 1415.52V = 1732.57 (17) Å3
Triclinic, P1Z = 1
a = 10.8399 (6) ÅMo Kα radiation
b = 11.6307 (7) ŵ = 0.10 mm1
c = 15.3585 (9) ÅT = 100 K
α = 73.480 (1)°0.44 × 0.39 × 0.25 mm
β = 73.554 (1)°
Data collection top
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 = 0.975Rint = 0.018
18068 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.03Δρmax = 0.75 e Å3
8578 reflectionsΔρmin = 0.48 e Å3
474 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*/Ueq
C10.6658 (2)0.6549 (2)1.01615 (13)0.0441 (5)
H10.71240.67111.05360.053*
C20.6637 (3)0.5315 (2)0.91362 (17)0.0663 (8)
H2A0.58100.59260.90630.099*
H2B0.64480.45010.94260.099*
H2C0.72320.52950.85240.099*
C30.8567 (3)0.4911 (3)0.97997 (19)0.0827 (10)
H3A0.89270.52541.01620.124*
H3B0.91430.49230.91780.124*
H3C0.85200.40601.01160.124*
C40.42933 (16)1.11176 (14)0.19126 (11)0.0250 (3)
H40.44981.16820.13390.030*
C50.47278 (18)0.90179 (15)0.28231 (12)0.0310 (3)
H5A0.40140.93840.32890.047*
H5B0.55340.86740.30670.047*
H5C0.44730.83610.26810.047*
C60.59696 (19)0.95763 (18)0.11855 (13)0.0367 (4)
H6A0.60501.02920.06670.055*
H6B0.57080.89650.09920.055*
H6C0.68210.92110.13670.055*
C70.04528 (16)0.06013 (14)0.13697 (10)0.0246 (3)
H70.11080.02230.18150.030*
C80.1655 (2)0.1142 (2)0.10120 (13)0.0458 (5)
H8A0.14180.15250.04070.069*
H8B0.24810.05100.09330.069*
H8C0.17730.17720.12710.069*
C90.08011 (18)0.00344 (16)0.25792 (11)0.0311 (3)
H9A0.00440.03900.29370.047*
H9B0.08790.05670.28850.047*
H9C0.16110.06910.25450.047*
C1A0.08449 (15)0.54655 (13)0.73022 (10)0.0221 (3)
H1A0.00290.55680.71420.026*
C2A0.10938 (15)0.64325 (14)0.75351 (11)0.0253 (3)
H2A10.04520.71910.75290.030*
C3A0.22786 (15)0.62924 (14)0.77765 (10)0.0244 (3)
C4A0.32319 (15)0.51968 (15)0.77624 (11)0.0261 (3)
H4A0.40540.51030.79120.031*
C5A0.29646 (15)0.42339 (14)0.75247 (10)0.0235 (3)
H5A10.36160.34830.75170.028*
C6A0.17776 (14)0.43408 (13)0.72994 (9)0.0184 (3)
C7A0.15459 (13)0.32867 (12)0.70084 (9)0.0168 (3)
H7A0.20820.25030.73220.020*
C8A0.20160 (13)0.33775 (12)0.59585 (9)0.0168 (3)
C9A0.21157 (14)0.23746 (12)0.55967 (10)0.0188 (3)
C10A0.24456 (14)0.24523 (13)0.46370 (10)0.0197 (3)
C11A0.27271 (14)0.35332 (13)0.40240 (9)0.0189 (3)
C12A0.26516 (13)0.45511 (12)0.43692 (9)0.0167 (3)
C13A0.22852 (13)0.44541 (12)0.53301 (9)0.0167 (3)
H13A0.22160.51470.55660.020*
C14A0.34920 (19)0.70947 (19)0.84427 (14)0.0371 (4)
H14A0.34670.63880.89740.056*
H14B0.34250.78320.86580.056*
H14C0.43260.69300.79870.056*
C1B0.19028 (14)0.75328 (13)0.44920 (10)0.0209 (3)
H1B0.11080.76160.43090.025*
C2B0.19295 (15)0.82921 (13)0.50364 (10)0.0227 (3)
H2B10.11570.88900.52220.027*
C3B0.30867 (15)0.81782 (13)0.53097 (10)0.0212 (3)
C4B0.42235 (15)0.73175 (13)0.50256 (10)0.0213 (3)
H4B0.50200.72440.52030.026*
C5B0.41803 (14)0.65622 (13)0.44765 (10)0.0193 (3)
H5B10.49580.59760.42810.023*
C6B0.30300 (14)0.66457 (12)0.42082 (9)0.0174 (3)
C7B0.29994 (13)0.57199 (12)0.36881 (9)0.0164 (3)
H7B0.39140.54720.33140.020*
C8B0.20893 (14)0.62977 (12)0.30071 (9)0.0175 (3)
C9B0.25441 (14)0.69388 (13)0.21136 (9)0.0190 (3)
C10B0.16993 (14)0.74998 (13)0.14914 (9)0.0203 (3)
C11B0.03791 (14)0.74173 (13)0.17682 (9)0.0196 (3)
C12B0.01042 (13)0.67990 (12)0.26735 (9)0.0177 (3)
C13B0.07631 (13)0.62514 (12)0.32698 (9)0.0174 (3)
H13B0.04370.58280.38820.021*
C14B0.41800 (18)0.88299 (17)0.61660 (14)0.0351 (4)
H14D0.45000.79700.64680.053*
H14E0.39880.93560.66080.053*
H14F0.48590.90830.56250.053*
N10.72534 (19)0.56446 (18)0.97160 (11)0.0471 (4)
N20.49696 (13)0.99649 (12)0.19751 (9)0.0254 (3)
N30.06071 (13)0.05763 (12)0.16428 (9)0.0256 (3)
O10.55477 (17)0.71894 (15)1.01234 (10)0.0533 (4)
O20.34118 (13)1.15300 (11)0.25381 (8)0.0315 (3)
O30.06606 (12)0.10807 (11)0.05755 (8)0.0312 (3)
O1A0.24155 (12)0.72893 (11)0.80213 (9)0.0330 (3)
O2A0.18662 (11)0.12992 (9)0.61961 (7)0.0235 (2)
H2A20.20890.07380.59000.035*
O3A0.24647 (13)0.14031 (10)0.43813 (8)0.0291 (3)
H3A10.27550.14830.38040.044*
O4A0.31128 (12)0.36441 (10)0.30769 (7)0.0251 (2)
H4A10.30960.29970.29450.038*
O1B0.30071 (11)0.89459 (10)0.58718 (8)0.0264 (2)
O2B0.38426 (10)0.70251 (11)0.18480 (7)0.0253 (2)
H2B20.40650.72070.12650.038*
O3B0.22783 (11)0.81115 (12)0.06305 (7)0.0305 (3)
H3B10.17260.83900.02890.046*
O4B0.05048 (11)0.79371 (11)0.11931 (7)0.0266 (2)
H4B10.01010.82110.06540.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0588 (13)0.0467 (11)0.0240 (8)0.0203 (10)0.0031 (8)0.0009 (8)
C20.107 (2)0.0506 (14)0.0404 (12)0.0024 (14)0.0303 (13)0.0113 (10)
C30.0444 (14)0.117 (3)0.0488 (14)0.0006 (15)0.0047 (11)0.0060 (15)
C40.0340 (8)0.0234 (7)0.0213 (7)0.0108 (6)0.0083 (6)0.0042 (5)
C50.0343 (9)0.0232 (8)0.0297 (8)0.0071 (6)0.0024 (7)0.0009 (6)
C60.0358 (9)0.0375 (9)0.0307 (9)0.0056 (7)0.0024 (7)0.0108 (7)
C70.0279 (7)0.0250 (7)0.0201 (7)0.0068 (6)0.0046 (6)0.0035 (6)
C80.0402 (10)0.0713 (14)0.0295 (9)0.0312 (10)0.0048 (8)0.0003 (9)
C90.0398 (9)0.0301 (8)0.0246 (7)0.0091 (7)0.0144 (7)0.0003 (6)
C1A0.0214 (7)0.0223 (7)0.0233 (7)0.0036 (5)0.0063 (5)0.0063 (5)
C2A0.0257 (7)0.0213 (7)0.0288 (7)0.0029 (6)0.0051 (6)0.0086 (6)
C3A0.0276 (7)0.0258 (7)0.0229 (7)0.0104 (6)0.0025 (6)0.0087 (6)
C4A0.0229 (7)0.0309 (8)0.0280 (7)0.0067 (6)0.0077 (6)0.0092 (6)
C5A0.0229 (7)0.0238 (7)0.0243 (7)0.0023 (6)0.0070 (6)0.0075 (6)
C6A0.0214 (6)0.0198 (6)0.0142 (6)0.0057 (5)0.0029 (5)0.0041 (5)
C7A0.0190 (6)0.0158 (6)0.0153 (6)0.0034 (5)0.0048 (5)0.0024 (5)
C8A0.0166 (6)0.0168 (6)0.0167 (6)0.0028 (5)0.0042 (5)0.0039 (5)
C9A0.0194 (6)0.0163 (6)0.0195 (6)0.0039 (5)0.0041 (5)0.0023 (5)
C10A0.0235 (7)0.0162 (6)0.0214 (7)0.0046 (5)0.0059 (5)0.0063 (5)
C11A0.0212 (6)0.0188 (6)0.0169 (6)0.0039 (5)0.0044 (5)0.0047 (5)
C12A0.0167 (6)0.0156 (6)0.0177 (6)0.0028 (5)0.0049 (5)0.0032 (5)
C13A0.0164 (6)0.0167 (6)0.0173 (6)0.0032 (5)0.0047 (5)0.0039 (5)
C14A0.0369 (9)0.0446 (10)0.0408 (10)0.0185 (8)0.0078 (8)0.0177 (8)
C1B0.0210 (7)0.0203 (7)0.0219 (7)0.0037 (5)0.0075 (5)0.0037 (5)
C2B0.0242 (7)0.0189 (7)0.0248 (7)0.0012 (5)0.0073 (6)0.0061 (5)
C3B0.0274 (7)0.0169 (6)0.0208 (6)0.0054 (5)0.0077 (5)0.0040 (5)
C4B0.0222 (7)0.0201 (7)0.0235 (7)0.0057 (5)0.0086 (5)0.0035 (5)
C5B0.0197 (6)0.0167 (6)0.0206 (6)0.0041 (5)0.0045 (5)0.0028 (5)
C6B0.0215 (6)0.0150 (6)0.0157 (6)0.0060 (5)0.0044 (5)0.0012 (5)
C7B0.0175 (6)0.0166 (6)0.0150 (6)0.0046 (5)0.0036 (5)0.0026 (5)
C8B0.0206 (6)0.0163 (6)0.0161 (6)0.0042 (5)0.0051 (5)0.0031 (5)
C9B0.0195 (6)0.0203 (6)0.0177 (6)0.0064 (5)0.0034 (5)0.0037 (5)
C10B0.0244 (7)0.0207 (6)0.0148 (6)0.0076 (5)0.0037 (5)0.0001 (5)
C11B0.0224 (7)0.0198 (6)0.0161 (6)0.0036 (5)0.0063 (5)0.0024 (5)
C12B0.0196 (6)0.0171 (6)0.0165 (6)0.0044 (5)0.0037 (5)0.0040 (5)
C13B0.0206 (6)0.0160 (6)0.0157 (6)0.0049 (5)0.0042 (5)0.0025 (5)
C14B0.0370 (9)0.0328 (9)0.0455 (10)0.0007 (7)0.0216 (8)0.0190 (8)
N10.0497 (10)0.0558 (11)0.0290 (8)0.0091 (8)0.0030 (7)0.0075 (7)
N20.0300 (7)0.0242 (6)0.0215 (6)0.0087 (5)0.0025 (5)0.0044 (5)
N30.0282 (7)0.0284 (7)0.0192 (6)0.0086 (5)0.0058 (5)0.0009 (5)
O10.0629 (10)0.0495 (9)0.0272 (7)0.0027 (7)0.0004 (6)0.0019 (6)
O20.0435 (7)0.0260 (6)0.0260 (6)0.0065 (5)0.0055 (5)0.0107 (5)
O30.0335 (6)0.0380 (7)0.0199 (5)0.0065 (5)0.0083 (5)0.0023 (5)
O1A0.0337 (6)0.0313 (6)0.0425 (7)0.0105 (5)0.0085 (5)0.0176 (5)
O2A0.0331 (6)0.0155 (5)0.0211 (5)0.0083 (4)0.0021 (4)0.0039 (4)
O3A0.0482 (7)0.0205 (5)0.0219 (5)0.0136 (5)0.0038 (5)0.0076 (4)
O4A0.0392 (6)0.0203 (5)0.0163 (5)0.0078 (5)0.0037 (4)0.0060 (4)
O1B0.0314 (6)0.0217 (5)0.0310 (6)0.0013 (4)0.0142 (5)0.0110 (4)
O2B0.0210 (5)0.0356 (6)0.0181 (5)0.0118 (4)0.0031 (4)0.0002 (4)
O3B0.0273 (6)0.0433 (7)0.0171 (5)0.0147 (5)0.0058 (4)0.0068 (5)
O4B0.0242 (5)0.0346 (6)0.0181 (5)0.0085 (5)0.0081 (4)0.0040 (4)
Geometric parameters (Å, º) top
C1—O11.224 (3)C8A—C13A1.3968 (18)
C1—N11.324 (3)C9A—O2A1.3736 (16)
C1—H10.9500C9A—C10A1.3976 (19)
C2—N11.438 (3)C10A—O3A1.3773 (16)
C2—H2A0.9800C10A—C11A1.3959 (19)
C2—H2B0.9800C11A—O4A1.3740 (16)
C2—H2C0.9800C11A—C12A1.4019 (18)
C3—N11.451 (3)C12A—C13A1.3957 (18)
C3—H3A0.9800C12A—C7B1.5336 (18)
C3—H3B0.9800C13A—H13A0.9500
C3—H3C0.9800C14A—O1A1.422 (2)
C4—O21.241 (2)C14A—H14A0.9800
C4—N21.318 (2)C14A—H14B0.9800
C4—H40.9500C14A—H14C0.9800
C5—N21.462 (2)C1B—C2B1.389 (2)
C5—H5A0.9800C1B—C6B1.402 (2)
C5—H5B0.9800C1B—H1B0.9500
C5—H5C0.9800C2B—C3B1.392 (2)
C6—N21.460 (2)C2B—H2B10.9500
C6—H6A0.9800C3B—O1B1.3788 (17)
C6—H6B0.9800C3B—C4B1.391 (2)
C6—H6C0.9800C4B—C5B1.397 (2)
C7—O31.2429 (19)C4B—H4B0.9500
C7—N31.320 (2)C5B—C6B1.3897 (19)
C7—H70.9500C5B—H5B10.9500
C8—N31.453 (2)C6B—C7B1.5243 (18)
C8—H8A0.9800C7B—C8B1.5218 (18)
C8—H8B0.9800C7B—H7B1.0000
C8—H8C0.9800C8B—C9B1.3899 (19)
C9—N31.456 (2)C8B—C13B1.3916 (19)
C9—H9A0.9800C9B—O2B1.3755 (17)
C9—H9B0.9800C9B—C10B1.403 (2)
C9—H9C0.9800C10B—O3B1.3801 (16)
C1A—C2A1.388 (2)C10B—C11B1.397 (2)
C1A—C6A1.400 (2)C11B—O4B1.3786 (17)
C1A—H1A0.9500C11B—C12B1.4015 (19)
C2A—C3A1.388 (2)C12B—C13B1.3907 (19)
C2A—H2A10.9500C12B—C7Ai1.5237 (19)
C3A—O1A1.3740 (18)C13B—H13B0.9500
C3A—C4A1.388 (2)C14B—O1B1.4244 (19)
C4A—C5A1.398 (2)C14B—H14D0.9800
C4A—H4A0.9500C14B—H14E0.9800
C5A—C6A1.387 (2)C14B—H14F0.9800
C5A—H5A10.9500O2A—H2A20.8400
C6A—C7A1.5235 (18)O3A—H3A10.8400
C7A—C12Bi1.5237 (19)O4A—H4A10.8400
C7A—C8A1.5298 (18)O2B—H2B20.8400
C7A—H7A1.0000O3B—H3B10.8400
C8A—C9A1.3936 (19)O4B—H4B10.8400
O1—C1—N1124.4 (2)O4A—C11A—C12A117.35 (12)
O1—C1—H1117.8C10A—C11A—C12A120.05 (12)
N1—C1—H1117.8C13A—C12A—C11A118.47 (12)
N1—C2—H2A109.5C13A—C12A—C7B122.12 (12)
N1—C2—H2B109.5C11A—C12A—C7B119.40 (12)
H2A—C2—H2B109.5C12A—C13A—C8A122.58 (12)
N1—C2—H2C109.5C12A—C13A—H13A118.7
H2A—C2—H2C109.5C8A—C13A—H13A118.7
H2B—C2—H2C109.5O1A—C14A—H14A109.5
N1—C3—H3A109.5O1A—C14A—H14B109.5
N1—C3—H3B109.5H14A—C14A—H14B109.5
H3A—C3—H3B109.5O1A—C14A—H14C109.5
N1—C3—H3C109.5H14A—C14A—H14C109.5
H3A—C3—H3C109.5H14B—C14A—H14C109.5
H3B—C3—H3C109.5C2B—C1B—C6B121.00 (13)
O2—C4—N2125.68 (15)C2B—C1B—H1B119.5
O2—C4—H4117.2C6B—C1B—H1B119.5
N2—C4—H4117.2C1B—C2B—C3B120.04 (13)
N2—C5—H5A109.5C1B—C2B—H2B1120.0
N2—C5—H5B109.5C3B—C2B—H2B1120.0
H5A—C5—H5B109.5O1B—C3B—C4B124.09 (13)
N2—C5—H5C109.5O1B—C3B—C2B115.86 (13)
H5A—C5—H5C109.5C4B—C3B—C2B120.04 (13)
H5B—C5—H5C109.5C3B—C4B—C5B119.19 (13)
N2—C6—H6A109.5C3B—C4B—H4B120.4
N2—C6—H6B109.5C5B—C4B—H4B120.4
H6A—C6—H6B109.5C6B—C5B—C4B121.76 (13)
N2—C6—H6C109.5C6B—C5B—H5B1119.1
H6A—C6—H6C109.5C4B—C5B—H5B1119.1
H6B—C6—H6C109.5C5B—C6B—C1B117.96 (12)
O3—C7—N3125.13 (15)C5B—C6B—C7B119.63 (12)
O3—C7—H7117.4C1B—C6B—C7B122.23 (12)
N3—C7—H7117.4C8B—C7B—C6B111.47 (11)
N3—C8—H8A109.5C8B—C7B—C12A112.53 (11)
N3—C8—H8B109.5C6B—C7B—C12A110.97 (11)
H8A—C8—H8B109.5C8B—C7B—H7B107.2
N3—C8—H8C109.5C6B—C7B—H7B107.2
H8A—C8—H8C109.5C12A—C7B—H7B107.2
H8B—C8—H8C109.5C9B—C8B—C13B117.81 (12)
N3—C9—H9A109.5C9B—C8B—C7B120.86 (12)
N3—C9—H9B109.5C13B—C8B—C7B121.27 (12)
H9A—C9—H9B109.5O2B—C9B—C8B118.78 (12)
N3—C9—H9C109.5O2B—C9B—C10B120.17 (12)
H9A—C9—H9C109.5C8B—C9B—C10B121.04 (13)
H9B—C9—H9C109.5O3B—C10B—C11B125.18 (13)
C2A—C1A—C6A121.08 (14)O3B—C10B—C9B114.94 (13)
C2A—C1A—H1A119.5C11B—C10B—C9B119.88 (12)
C6A—C1A—H1A119.5O4B—C11B—C10B123.10 (12)
C3A—C2A—C1A120.07 (14)O4B—C11B—C12B117.05 (12)
C3A—C2A—H2A1120.0C10B—C11B—C12B119.85 (13)
C1A—C2A—H2A1120.0C13B—C12B—C11B118.63 (13)
O1A—C3A—C4A124.20 (14)C13B—C12B—C7Ai120.78 (12)
O1A—C3A—C2A115.68 (14)C11B—C12B—C7Ai120.58 (12)
C4A—C3A—C2A120.12 (14)C12B—C13B—C8B122.76 (13)
C3A—C4A—C5A118.97 (14)C12B—C13B—H13B118.6
C3A—C4A—H4A120.5C8B—C13B—H13B118.6
C5A—C4A—H4A120.5O1B—C14B—H14D109.5
C6A—C5A—C4A122.06 (14)O1B—C14B—H14E109.5
C6A—C5A—H5A1119.0H14D—C14B—H14E109.5
C4A—C5A—H5A1119.0O1B—C14B—H14F109.5
C5A—C6A—C1A117.67 (13)H14D—C14B—H14F109.5
C5A—C6A—C7A120.40 (12)H14E—C14B—H14F109.5
C1A—C6A—C7A121.84 (12)C1—N1—C2122.4 (2)
C6A—C7A—C12Bi111.99 (11)C1—N1—C3121.5 (2)
C6A—C7A—C8A111.96 (11)C2—N1—C3116.0 (2)
C12Bi—C7A—C8A110.42 (11)C4—N2—C6120.99 (14)
C6A—C7A—H7A107.4C4—N2—C5121.72 (13)
C12Bi—C7A—H7A107.4C6—N2—C5117.27 (14)
C8A—C7A—H7A107.4C7—N3—C8121.29 (14)
C9A—C8A—C13A117.73 (12)C7—N3—C9122.09 (14)
C9A—C8A—C7A119.38 (12)C8—N3—C9116.61 (14)
C13A—C8A—C7A122.79 (12)C3A—O1A—C14A116.79 (13)
O2A—C9A—C8A119.20 (12)C9A—O2A—H2A2109.5
O2A—C9A—C10A119.68 (12)C10A—O3A—H3A1109.5
C8A—C9A—C10A121.11 (12)C11A—O4A—H4A1109.5
O3A—C10A—C11A125.35 (13)C3B—O1B—C14B116.51 (12)
O3A—C10A—C9A114.62 (12)C9B—O2B—H2B2109.5
C11A—C10A—C9A120.02 (12)C10B—O3B—H3B1109.5
O4A—C11A—C10A122.58 (12)C11B—O4B—H4B1109.5
C6A—C1A—C2A—C3A0.4 (2)C4B—C5B—C6B—C7B174.18 (12)
C1A—C2A—C3A—O1A178.20 (14)C2B—C1B—C6B—C5B1.0 (2)
C1A—C2A—C3A—C4A1.7 (2)C2B—C1B—C6B—C7B174.18 (13)
O1A—C3A—C4A—C5A178.30 (14)C5B—C6B—C7B—C8B147.78 (12)
C2A—C3A—C4A—C5A1.6 (2)C1B—C6B—C7B—C8B37.16 (17)
C3A—C4A—C5A—C6A0.2 (2)C5B—C6B—C7B—C12A85.95 (15)
C4A—C5A—C6A—C1A1.0 (2)C1B—C6B—C7B—C12A89.11 (15)
C4A—C5A—C6A—C7A177.66 (13)C13A—C12A—C7B—C8B119.55 (14)
C2A—C1A—C6A—C5A0.9 (2)C11A—C12A—C7B—C8B61.78 (16)
C2A—C1A—C6A—C7A177.51 (13)C13A—C12A—C7B—C6B6.13 (18)
C5A—C6A—C7A—C12Bi146.61 (13)C11A—C12A—C7B—C6B172.53 (12)
C1A—C6A—C7A—C12Bi36.85 (17)C6B—C7B—C8B—C9B85.55 (15)
C5A—C6A—C7A—C8A88.73 (15)C12A—C7B—C8B—C9B149.04 (13)
C1A—C6A—C7A—C8A87.80 (16)C6B—C7B—C8B—C13B91.47 (15)
C6A—C7A—C8A—C9A167.71 (12)C12A—C7B—C8B—C13B33.94 (17)
C12Bi—C7A—C8A—C9A66.78 (16)C13B—C8B—C9B—O2B178.24 (12)
C6A—C7A—C8A—C13A15.94 (18)C7B—C8B—C9B—O2B1.1 (2)
C12Bi—C7A—C8A—C13A109.57 (14)C13B—C8B—C9B—C10B1.2 (2)
C13A—C8A—C9A—O2A179.57 (12)C7B—C8B—C9B—C10B178.36 (13)
C7A—C8A—C9A—O2A3.90 (19)O2B—C9B—C10B—O3B0.1 (2)
C13A—C8A—C9A—C10A1.4 (2)C8B—C9B—C10B—O3B179.62 (13)
C7A—C8A—C9A—C10A175.16 (13)O2B—C9B—C10B—C11B179.47 (13)
O2A—C9A—C10A—O3A1.1 (2)C8B—C9B—C10B—C11B0.0 (2)
C8A—C9A—C10A—O3A177.96 (13)O3B—C10B—C11B—O4B0.9 (2)
O2A—C9A—C10A—C11A178.68 (13)C9B—C10B—C11B—O4B179.53 (13)
C8A—C9A—C10A—C11A2.3 (2)O3B—C10B—C11B—C12B178.10 (14)
O3A—C10A—C11A—O4A2.7 (2)C9B—C10B—C11B—C12B1.5 (2)
C9A—C10A—C11A—O4A177.09 (13)O4B—C11B—C12B—C13B179.29 (12)
O3A—C10A—C11A—C12A178.87 (13)C10B—C11B—C12B—C13B1.7 (2)
C9A—C10A—C11A—C12A1.4 (2)O4B—C11B—C12B—C7Ai0.19 (19)
O4A—C11A—C12A—C13A178.86 (12)C10B—C11B—C12B—C7Ai179.25 (12)
C10A—C11A—C12A—C13A0.3 (2)C11B—C12B—C13B—C8B0.4 (2)
O4A—C11A—C12A—C7B0.15 (19)C7Ai—C12B—C13B—C8B179.48 (12)
C10A—C11A—C12A—C7B178.40 (12)C9B—C8B—C13B—C12B1.1 (2)
C11A—C12A—C13A—C8A1.2 (2)C7B—C8B—C13B—C12B178.16 (12)
C7B—C12A—C13A—C8A177.46 (12)O1—C1—N1—C20.4 (3)
C9A—C8A—C13A—C12A0.4 (2)O1—C1—N1—C3179.3 (2)
C7A—C8A—C13A—C12A176.78 (12)O2—C4—N2—C6178.74 (16)
C6B—C1B—C2B—C3B0.1 (2)O2—C4—N2—C50.5 (3)
C1B—C2B—C3B—O1B178.13 (13)O3—C7—N3—C80.6 (3)
C1B—C2B—C3B—C4B1.0 (2)O3—C7—N3—C9178.20 (16)
O1B—C3B—C4B—C5B178.18 (13)C4A—C3A—O1A—C14A11.8 (2)
C2B—C3B—C4B—C5B0.9 (2)C2A—C3A—O1A—C14A168.08 (15)
C3B—C4B—C5B—C6B0.2 (2)C4B—C3B—O1B—C14B0.2 (2)
C4B—C5B—C6B—C1B1.1 (2)C2B—C3B—O1B—C14B179.30 (14)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4B—H4B1···O3B0.842.542.9446 (16)111
O4B—H4B1···O3ii0.841.892.7231 (15)175
O3B—H3B1···O4B0.842.552.9446 (16)110
O3B—H3B1···O3ii0.841.862.6971 (16)173
O2B—H2B2···O3B0.842.262.6773 (15)111
O2B—H2B2···O1iii0.842.022.7595 (18)147
O4A—H4A1···O3A0.842.522.9334 (15)112
O4A—H4A1···O2iv0.841.892.7158 (15)169
O3A—H3A1···O4A0.842.542.9334 (15)110
O3A—H3A1···O2iv0.841.862.7010 (16)176
O2A—H2A2···O3A0.842.202.6523 (15)114
O2A—H2A2···O1Biv0.842.042.7779 (15)147
Symmetry codes: (ii) x, y+1, z; (iii) x, y, z1; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC56H48O16·6C3H7NO
Mr1415.52
Crystal system, space groupTriclinic, 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)
V3)1732.57 (17)
Z1
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.44 × 0.39 × 0.25
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS in SAINT-Plus; Bruker, 2003b)
Tmin, Tmax0.889, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
18068, 8578, 7224
Rint0.018
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.143, 1.03
No. of reflections8578
No. of parameters474
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.75, 0.48

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003b), SAINT-Plus, SHELXTL (Bruker, 2003a), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4B—H4B1···O3B0.842.542.9446 (16)110.9
O4B—H4B1···O3i0.841.892.7231 (15)174.9
O3B—H3B1···O4B0.842.552.9446 (16)110.3
O3B—H3B1···O3i0.841.862.6971 (16)173.1
O2B—H2B2···O3B0.842.262.6773 (15)111.0
O2B—H2B2···O1ii0.842.022.7595 (18)147.3
O4A—H4A1···O3A0.842.522.9334 (15)111.8
O4A—H4A1···O2iii0.841.892.7158 (15)168.7
O3A—H3A1···O4A0.842.542.9334 (15)110.0
O3A—H3A1···O2iii0.841.862.7010 (16)175.5
O2A—H2A2···O3A0.842.202.6523 (15)114.0
O2A—H2A2···O1Biii0.842.042.7779 (15)146.7
Symmetry codes: (i) x, y+1, z; (ii) x, y, z1; (iii) x, y1, z.
 

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