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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1389–o1390.
Published online 2009 May 23. doi:  10.1107/S1600536809018431
PMCID: PMC2969663

threo-2-(2,6-Dimethoxy­phen­oxy)-1-(4-eth­oxy-3-methoxy­phen­yl)propane-1,3-diol

Abstract

In the crystal structure of the title compound, C20H26O7, a lignin model compound, the asymmetric unit contains two mol­ecules which adopt almost identical overall conformations with some deviation in the region of the terminal hydroxyl groups. The two mol­ecules are linked by an inter­molecular O—H(...)O hydrogen bond. They also develop intra­molecular O—H(...)O hydrogen bonds.

Related literature

For the synthesis, see: von Unge et al. (1988 [triangle]). For the crystal structure of two related guaiacyl­glycerol β-syringyl ether type lignin model dimers, see: Langer, Li et al. (2002 [triangle]); Langer, Lundquist et al. (2002 [triangle]). For the crystal structure of several related syringylglycerol β-syringyl ethers, see: Langer & Lundquist (2001 [triangle]); Langer, Li et al. (2002 [triangle]); Langer, Lundquist et al. (2002 [triangle]); Langer et al. (2005 [triangle]); Lundquist et al. (2005 [triangle]); Stomberg & Lundquist (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1389-scheme1.jpg

Experimental

Crystal data

  • C20H26O7
  • M r = 378.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1389-efi1.jpg
  • a = 9.929 (4) Å
  • b = 28.066 (10) Å
  • c = 13.985 (5) Å
  • β = 100.954 (2)°
  • V = 3826 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 173 K
  • 0.50 × 0.50 × 0.40 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: numerical (CrystalClear; Rigaku, 2006 [triangle]) T min = 0.938, T max = 0.961
  • 30389 measured reflections
  • 8726 independent reflections
  • 3941 reflections with F 2 > 2σ(F 2)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.227
  • S = 1.00
  • 8726 reflections
  • 539 parameters
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: CrystalClear (Rigaku, 2006 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2007 [triangle]); program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: CRYSTALS (Carruthers et al., 1999 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018431/bx2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018431/bx2203Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Ministry of Education, Culture, Sports, Science and Technology of Japan for financial support via Grants-in-Aid for Scientific Research on Priority Areas ‘Synergy of Elements’ (MN, 18064006) and for Young Scientists from JSPS (S, MN, 2075003). Financial and facility support from the System for Development and Assessment of Sustainable Humanosphere, Center for Ecological Research, Research Institute for Sustainable Humanosphere, Kyoto University, is also acknowledged.

supplementary crystallographic information

Comment

Lignin is a complex biopolymer consisting of p-hydroxyphenyl, guaiacyl and syringyl phenylpropanoid monomer units. Aryl glycerol β-syringyl ethers are the main structural elements in hardwood lignins. The crystal structure of threo-2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1,3- propanediol (Langer, Li et al., 2002; Langer, Lundquist et al., 2002) and several syringylglycerol β-syringyl ethers are reported. We have prepared a guaiacylglycerol β-syringyl ether type lignin model dimer having an ethyl ether substituent at 4-position, which does not show a similar packing structure or hydrogen bonding network to that of the methyl ether counterpart.

There are two molecules of the title compound in the asymmetric unit (Fig. 1). The conformations of two molecules are similar, as indicated by the torsion angles of 59.1 (3) and 61.3 (3)° along the phenylpropanoid skeleton (C1—C10—C11—C12 and C21—C30—C31—C32), respectively. They are connected with each other by the hydrogen bond of O11—H11···O4 through the terminal hydroxyl groups. Intramolecular hydrogen bonds of O3—H3···O6, O4—H4···O7 and O10—H10···O13 are also present (Table 1).

Experimental

The title compound was synthesized in two steps with a procedure similar to that reported in the literature (von Unge et al., 1988). Separation of the erythro and threo forms of the first step product was accomplished by recrystallization from methanol to give threo-3-(4-ethoxy-3-methoxyphenyl)-2-(2,6-Dimethoxyphenoxy)- -3-hydroxypropanoic acid 1. The title compound, threo-1-(4-ethoxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-1,3- propanediol, was synthesized from 1, and Single crystals of that suitable for X-ray crystallography were obtained from methanol.

Refinement

All H atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 (aromatic), 0.96 (methyl), 0.97 (methylene), 0.98 (methine) and 0.82 Å (hydroxyl), and with Uiso(H) = xUeq (carrier atom), where x = 1.5 for methyl and hydroxyl groups and x = 1.2 for other H atoms.

Figures

Fig. 1.
A view of the molecular structure of the title compound, which is an asymmetric unit with two molecules, with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Dash lines indicate hydrogen bonds.

Crystal data

C20H26O7F(000) = 1616.00
Mr = 378.42Dx = 1.314 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 7455 reflections
a = 9.929 (4) Åθ = 3.0–27.5°
b = 28.066 (10) ŵ = 0.10 mm1
c = 13.985 (5) ÅT = 173 K
β = 100.954 (2)°Block, colorless
V = 3826 (2) Å30.50 × 0.50 × 0.40 mm
Z = 8

Data collection

Rigaku Saturn diffractometer3941 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.056
ω scansθmax = 27.5°
Absorption correction: numerical (CrystalClear; Rigaku, 2006)h = −11→12
Tmin = 0.938, Tmax = 0.961k = −35→36
30389 measured reflectionsl = −18→16
8726 independent reflections

Refinement

Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.074w = 1/[0.0018Fo2 + σ(Fo2)]/(4Fo2)
wR(F2) = 0.227(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.59 e Å3
8726 reflectionsΔρmin = −0.67 e Å3
539 parameters

Special details

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O(1)0.4275 (2)0.14739 (7)0.32648 (14)0.0342 (6)
O(2)0.6049 (2)0.07942 (7)0.34454 (14)0.0303 (5)
O(3)0.3267 (2)0.07866 (7)0.71410 (14)0.0320 (6)
O(4)0.5503 (2)0.23444 (8)0.73756 (17)0.0475 (7)
O(5)0.3404 (2)0.16987 (8)0.80643 (14)0.0327 (6)
O(6)0.1968 (2)0.09850 (8)0.86837 (14)0.0347 (6)
O(7)0.5527 (2)0.21120 (9)0.92951 (16)0.0478 (7)
O(8)0.9339 (2)0.15184 (8)0.33101 (15)0.0372 (6)
O(9)1.1062 (2)0.08238 (7)0.34465 (14)0.0308 (5)
O(10)0.8242 (2)0.07441 (7)0.71045 (14)0.0307 (5)
O(11)0.7854 (2)0.22309 (8)0.64640 (16)0.0475 (7)
O(12)0.8095 (2)0.16035 (7)0.80390 (14)0.0296 (5)
O(13)0.6895 (2)0.08724 (8)0.87353 (15)0.0357 (6)
O(14)1.0163 (2)0.20864 (9)0.91436 (17)0.0518 (8)
C(1)0.4133 (3)0.10906 (10)0.5791 (2)0.0241 (7)
C(2)0.3838 (3)0.13478 (10)0.49118 (19)0.0260 (7)
C(3)0.4498 (3)0.12462 (10)0.4152 (2)0.0262 (7)
C(4)0.5457 (3)0.08738 (10)0.42410 (19)0.0242 (7)
C(5)0.5741 (3)0.06160 (10)0.5105 (2)0.0262 (7)
C(6)0.5080 (3)0.07258 (10)0.5872 (2)0.0253 (7)
C(7)0.3190 (3)0.18146 (11)0.3079 (2)0.0390 (9)
C(8)0.6995 (3)0.04042 (10)0.3506 (2)0.0296 (8)
C(9)0.7502 (3)0.03888 (13)0.2561 (2)0.0419 (10)
C(10)0.3426 (3)0.12164 (10)0.6632 (2)0.0271 (7)
C(11)0.4245 (3)0.15808 (10)0.7333 (2)0.0268 (7)
C(12)0.4476 (3)0.20437 (11)0.6829 (2)0.0361 (9)
C(13)0.3800 (3)0.15276 (11)0.9010 (2)0.0310 (8)
C(14)0.3031 (3)0.11713 (12)0.9350 (2)0.0306 (8)
C(15)0.3344 (3)0.10274 (13)1.0327 (2)0.0364 (9)
C(16)0.4424 (3)0.12367 (13)1.0950 (2)0.0396 (9)
C(17)0.5179 (3)0.15965 (13)1.0630 (2)0.0394 (9)
C(18)0.4864 (3)0.17446 (12)0.9666 (2)0.0336 (8)
C(19)0.1179 (3)0.06067 (12)0.9001 (2)0.0399 (10)
C(20)0.6557 (4)0.23658 (15)0.9951 (2)0.0607 (13)
C(21)0.9136 (3)0.10908 (10)0.57963 (19)0.0245 (7)
C(22)0.8872 (3)0.13658 (10)0.4944 (2)0.0267 (7)
C(23)0.9542 (3)0.12739 (10)0.4183 (2)0.0267 (7)
C(24)1.0484 (3)0.08982 (10)0.4250 (2)0.0257 (7)
C(25)1.0758 (3)0.06276 (11)0.5098 (2)0.0275 (8)
C(26)1.0083 (3)0.07255 (10)0.5861 (2)0.0272 (7)
C(27)0.8261 (3)0.18541 (12)0.3144 (2)0.0431 (10)
C(28)1.1946 (3)0.04152 (11)0.3470 (2)0.0326 (8)
C(29)1.2407 (4)0.03979 (13)0.2500 (2)0.0456 (10)
C(30)0.8354 (3)0.11832 (10)0.66079 (19)0.0246 (7)
C(31)0.9029 (3)0.15579 (10)0.7346 (2)0.0273 (7)
C(32)0.9155 (3)0.20479 (11)0.6913 (2)0.0342 (9)
C(33)0.8574 (3)0.14663 (11)0.8994 (2)0.0301 (8)
C(34)0.7920 (3)0.10971 (12)0.9378 (2)0.0311 (8)
C(35)0.8316 (3)0.09725 (14)1.0365 (2)0.0433 (10)
C(36)0.9362 (3)0.12216 (15)1.0940 (2)0.0477 (11)
C(37)1.0023 (3)0.15938 (15)1.0574 (2)0.0494 (11)
C(38)0.9632 (3)0.17161 (12)0.9596 (2)0.0366 (9)
C(39)0.6114 (3)0.05122 (12)0.9101 (2)0.0439 (10)
C(40)1.1206 (4)0.23640 (16)0.9716 (3)0.0668 (14)
H(2)0.31860.15900.48410.031*
H(5)0.63760.03690.51730.031*
H(6)0.52780.05510.64460.030*
H(15)0.28260.07911.05530.045*
H(16)0.46460.11351.15940.048*
H(17)0.58970.17391.10590.047*
H(22)0.82370.16130.48910.032*
H(25)1.13930.03810.51560.033*
H(26)1.02730.05420.64250.033*
H(35)0.78790.07251.06260.053*
H(36)0.96290.11381.15920.057*
H(37)1.07210.17601.09760.059*
H(10A)0.25170.13480.63700.033*
H(11A)0.51240.14440.76520.033*
H(30)0.74290.12930.63180.030*
H(31)0.99300.14460.76820.033*
H(8A)0.77580.04540.40430.036*
H(8B)0.65360.01080.36020.036*
H(12A)0.36150.22160.66950.043*
H(12B)0.47600.19670.62210.043*
H(28A)1.27330.04470.39960.041*
H(28B)1.14480.01270.35630.040*
H(32A)0.97350.20250.64290.041*
H(32B)0.95700.22630.74280.041*
H(7A)0.23550.16580.27840.048*
H(7B)0.34090.20560.26480.048*
H(7C)0.30750.19590.36810.048*
H(19A)0.15820.03050.88920.049*
H(19B)0.02550.06190.86390.049*
H(19C)0.11720.06440.96820.049*
H(20A)0.61460.26301.02250.075*
H(20B)0.72390.24820.96050.075*
H(20C)0.69800.21561.04630.075*
H(27A)0.74320.17000.28270.053*
H(27B)0.84850.21060.27360.053*
H(27C)0.81300.19840.37540.052*
H(39A)0.65490.02090.90680.056*
H(39B)0.52040.05030.87170.055*
H(39C)0.60660.05820.97660.055*
H(40A)1.07980.26241.00020.081*
H(40B)1.18090.24860.93120.081*
H(40C)1.17200.21691.02210.081*
H(9A)0.69110.01880.21070.053*
H(9B)0.84180.02630.26720.053*
H(9C)0.75010.07050.22990.053*
H(3)0.32860.08460.77170.040*
H(29A)1.17690.02120.20480.058*
H(29B)1.33010.02550.25860.058*
H(29C)1.24460.07160.22530.058*
H(4)0.51380.25240.77130.058*
H(10)0.82140.07990.76770.038*
H(11)0.72600.21250.67410.057*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O(1)0.0501 (14)0.0351 (12)0.0190 (10)0.0097 (10)0.0106 (9)0.0096 (8)
O(2)0.0363 (13)0.0358 (11)0.0216 (10)0.0068 (10)0.0121 (9)0.0019 (8)
O(3)0.0427 (13)0.0333 (11)0.0228 (10)−0.0069 (10)0.0131 (9)−0.0002 (8)
O(4)0.0571 (17)0.0383 (13)0.0485 (14)−0.0046 (12)0.0134 (12)−0.0073 (11)
O(5)0.0382 (13)0.0441 (13)0.0178 (10)0.0123 (10)0.0100 (9)0.0017 (9)
O(6)0.0318 (12)0.0519 (14)0.0216 (10)−0.0016 (10)0.0081 (9)0.0005 (9)
O(7)0.0552 (17)0.0563 (15)0.0331 (12)−0.0172 (13)0.0115 (11)−0.0087 (11)
O(8)0.0493 (15)0.0416 (13)0.0234 (10)0.0132 (11)0.0139 (10)0.0109 (9)
O(9)0.0384 (13)0.0334 (11)0.0236 (10)0.0044 (9)0.0136 (9)0.0017 (8)
O(10)0.0415 (13)0.0300 (11)0.0224 (10)−0.0044 (9)0.0104 (9)−0.0004 (8)
O(11)0.0620 (18)0.0404 (13)0.0394 (13)−0.0062 (12)0.0077 (12)0.0078 (10)
O(12)0.0345 (12)0.0377 (12)0.0174 (9)0.0038 (10)0.0069 (8)−0.0001 (8)
O(13)0.0365 (13)0.0475 (13)0.0255 (11)−0.0025 (10)0.0117 (9)0.0032 (9)
O(14)0.0590 (17)0.0576 (16)0.0393 (14)−0.0221 (14)0.0111 (12)−0.0151 (12)
C(1)0.0261 (16)0.0270 (15)0.0198 (13)−0.0055 (12)0.0054 (11)−0.0026 (11)
C(2)0.0308 (17)0.0258 (15)0.0214 (14)0.0031 (13)0.0044 (12)−0.0006 (11)
C(3)0.0358 (18)0.0248 (15)0.0177 (13)0.0012 (13)0.0049 (12)0.0016 (11)
C(4)0.0244 (15)0.0303 (15)0.0191 (13)−0.0027 (12)0.0072 (11)−0.0034 (11)
C(5)0.0275 (16)0.0271 (15)0.0247 (14)−0.0005 (13)0.0067 (12)0.0024 (11)
C(6)0.0259 (16)0.0296 (15)0.0195 (13)−0.0032 (13)0.0021 (12)0.0029 (11)
C(7)0.056 (2)0.0333 (17)0.0290 (17)0.0142 (16)0.0112 (16)0.0086 (14)
C(8)0.0323 (18)0.0249 (15)0.0332 (16)0.0015 (13)0.0106 (14)0.0002 (12)
C(9)0.049 (2)0.048 (2)0.0348 (17)0.0028 (17)0.0235 (16)−0.0029 (15)
C(10)0.0289 (16)0.0329 (16)0.0199 (14)−0.0009 (13)0.0062 (12)0.0012 (12)
C(11)0.0300 (16)0.0321 (16)0.0194 (13)0.0027 (13)0.0076 (12)0.0004 (12)
C(12)0.052 (2)0.0299 (16)0.0259 (15)−0.0069 (15)0.0056 (15)−0.0043 (13)
C(13)0.0329 (18)0.0421 (18)0.0178 (13)0.0096 (15)0.0047 (12)−0.0014 (12)
C(14)0.0275 (17)0.0443 (19)0.0208 (14)0.0047 (14)0.0065 (12)−0.0036 (13)
C(15)0.0345 (18)0.058 (2)0.0200 (15)0.0029 (16)0.0121 (13)0.0029 (14)
C(16)0.044 (2)0.057 (2)0.0189 (15)0.0063 (18)0.0094 (14)0.0012 (14)
C(17)0.0332 (19)0.060 (2)0.0245 (16)−0.0016 (17)0.0039 (14)−0.0100 (15)
C(18)0.0365 (19)0.0431 (19)0.0243 (15)−0.0003 (15)0.0136 (13)−0.0048 (13)
C(19)0.036 (2)0.050 (2)0.0362 (18)−0.0038 (16)0.0124 (15)−0.0040 (15)
C(20)0.071 (3)0.070 (2)0.046 (2)−0.028 (2)0.024 (2)−0.024 (2)
C(21)0.0291 (16)0.0282 (15)0.0167 (13)−0.0052 (13)0.0060 (11)−0.0021 (11)
C(22)0.0296 (17)0.0283 (15)0.0227 (14)0.0040 (13)0.0066 (12)0.0001 (12)
C(23)0.0326 (17)0.0297 (15)0.0181 (13)−0.0004 (13)0.0056 (12)0.0042 (11)
C(24)0.0281 (16)0.0303 (16)0.0202 (14)−0.0006 (13)0.0086 (12)−0.0015 (11)
C(25)0.0274 (16)0.0306 (16)0.0259 (15)0.0030 (13)0.0083 (12)0.0032 (12)
C(26)0.0294 (17)0.0321 (16)0.0199 (14)−0.0020 (13)0.0041 (12)0.0039 (12)
C(27)0.055 (2)0.044 (2)0.0307 (17)0.0150 (18)0.0102 (16)0.0121 (15)
C(28)0.041 (2)0.0267 (16)0.0339 (17)0.0018 (14)0.0170 (15)0.0001 (13)
C(29)0.056 (2)0.048 (2)0.0412 (19)0.0014 (18)0.0292 (18)−0.0037 (16)
C(30)0.0278 (16)0.0270 (15)0.0197 (13)−0.0041 (13)0.0061 (12)−0.0014 (11)
C(31)0.0279 (17)0.0344 (16)0.0207 (14)−0.0015 (13)0.0077 (12)−0.0029 (12)
C(32)0.045 (2)0.0308 (16)0.0271 (16)−0.0052 (15)0.0072 (14)−0.0020 (13)
C(33)0.0283 (17)0.0454 (19)0.0174 (13)0.0060 (14)0.0065 (12)−0.0045 (13)
C(34)0.0270 (17)0.0464 (19)0.0210 (14)0.0049 (14)0.0072 (12)−0.0036 (13)
C(35)0.043 (2)0.069 (2)0.0204 (15)0.0116 (19)0.0134 (15)0.0080 (15)
C(36)0.047 (2)0.080 (2)0.0168 (15)0.011 (2)0.0063 (15)−0.0012 (17)
C(37)0.042 (2)0.084 (2)0.0226 (16)0.002 (2)0.0071 (15)−0.0151 (18)
C(38)0.0382 (19)0.048 (2)0.0244 (16)0.0035 (16)0.0074 (14)−0.0080 (14)
C(39)0.043 (2)0.046 (2)0.048 (2)−0.0008 (17)0.0241 (17)0.0039 (17)
C(40)0.057 (2)0.075 (3)0.071 (2)−0.020 (2)0.018 (2)−0.036 (2)

Geometric parameters (Å, °)

O(1)—C(3)1.375 (3)C(36)—C(37)1.383 (5)
O(1)—C(7)1.427 (4)C(37)—C(38)1.392 (4)
O(2)—C(4)1.372 (3)O(3)—H(3)0.819
O(2)—C(8)1.434 (3)O(4)—H(4)0.821
O(3)—C(10)1.424 (3)O(10)—H(10)0.820
O(4)—C(12)1.428 (3)O(11)—H(11)0.820
O(5)—C(11)1.475 (3)C(2)—H(2)0.930
O(5)—C(13)1.392 (3)C(5)—H(5)0.930
O(6)—C(14)1.371 (3)C(6)—H(6)0.930
O(6)—C(19)1.439 (4)C(7)—H(7A)0.960
O(7)—C(18)1.377 (4)C(7)—H(7B)0.960
O(7)—C(20)1.427 (4)C(7)—H(7C)0.960
O(8)—C(23)1.381 (3)C(8)—H(8A)0.970
O(8)—C(27)1.412 (4)C(8)—H(8B)0.970
O(9)—C(24)1.371 (3)C(9)—H(9A)0.960
O(9)—C(28)1.441 (3)C(9)—H(9B)0.960
O(10)—C(30)1.429 (3)C(9)—H(9C)0.960
O(11)—C(32)1.421 (4)C(10)—H(10A)0.980
O(12)—C(31)1.469 (3)C(11)—H(11A)0.980
O(12)—C(33)1.384 (3)C(12)—H(12A)0.970
O(13)—C(34)1.376 (3)C(12)—H(12B)0.970
O(13)—C(39)1.427 (4)C(15)—H(15)0.930
O(14)—C(38)1.373 (4)C(16)—H(16)0.930
O(14)—C(40)1.416 (4)C(17)—H(17)0.930
C(1)—C(2)1.408 (3)C(19)—H(19A)0.960
C(1)—C(6)1.380 (4)C(19)—H(19B)0.960
C(1)—C(10)1.521 (4)C(19)—H(19C)0.960
C(2)—C(3)1.381 (4)C(20)—H(20A)0.960
C(3)—C(4)1.404 (4)C(20)—H(20B)0.960
C(4)—C(5)1.391 (3)C(20)—H(20C)0.960
C(5)—C(6)1.395 (4)C(22)—H(22)0.930
C(8)—C(9)1.501 (4)C(25)—H(25)0.930
C(10)—C(11)1.538 (3)C(26)—H(26)0.930
C(11)—C(12)1.516 (4)C(27)—H(27A)0.960
C(13)—C(14)1.395 (4)C(27)—H(27B)0.960
C(13)—C(18)1.400 (4)C(27)—H(27C)0.960
C(14)—C(15)1.402 (4)C(28)—H(28A)0.970
C(15)—C(16)1.378 (4)C(28)—H(28B)0.970
C(16)—C(17)1.383 (5)C(29)—H(29A)0.960
C(17)—C(18)1.388 (4)C(29)—H(29B)0.960
C(21)—C(22)1.402 (3)C(29)—H(29C)0.960
C(21)—C(26)1.383 (4)C(30)—H(30)0.980
C(21)—C(30)1.515 (4)C(31)—H(31)0.980
C(22)—C(23)1.383 (4)C(32)—H(32A)0.970
C(23)—C(24)1.401 (4)C(32)—H(32B)0.970
C(24)—C(25)1.392 (3)C(35)—H(35)0.930
C(25)—C(26)1.391 (4)C(36)—H(36)0.930
C(28)—C(29)1.512 (5)C(37)—H(37)0.930
C(30)—C(31)1.535 (3)C(39)—H(39A)0.960
C(31)—C(32)1.518 (4)C(39)—H(39B)0.960
C(33)—C(34)1.384 (4)C(39)—H(39C)0.960
C(33)—C(38)1.403 (4)C(40)—H(40A)0.960
C(34)—C(35)1.405 (4)C(40)—H(40B)0.960
C(35)—C(36)1.377 (4)C(40)—H(40C)0.960
O(1)···C(16)i3.335 (3)H(36)···H(29C)ix3.017
O(1)···C(29)ii3.598 (4)H(37)···O(4)iv3.219
O(2)···C(22)3.548 (3)H(37)···O(11)iv3.525
O(3)···C(8)iii3.459 (3)H(37)···C(7)xv3.456
O(3)···C(9)iii3.429 (4)H(37)···C(15)vi3.567
O(3)···C(25)ii3.444 (3)H(37)···H(15)vi3.545
O(3)···C(26)ii3.328 (3)H(37)···H(7A)xv2.747
O(4)···O(11)2.882 (3)H(37)···H(7B)xv3.303
O(4)···O(12)3.301 (3)H(37)···H(4)iv3.289
O(4)···C(7)iv3.558 (4)H(37)···H(11)iv3.558
O(4)···C(27)v3.475 (4)H(10A)···C(21)ii3.378
O(6)···C(31)ii3.540 (3)H(10A)···C(24)ii3.491
O(6)···C(38)ii3.513 (4)H(10A)···C(25)ii3.021
O(8)···C(36)i3.422 (3)H(10A)···C(26)ii2.958
O(9)···C(2)vi3.436 (3)H(10A)···H(25)ii3.284
O(9)···C(3)vi3.569 (3)H(10A)···H(26)ii3.187
O(9)···C(7)vi3.588 (4)H(10A)···H(31)ii3.440
O(10)···C(5)3.387 (3)H(10A)···H(32A)ii3.367
O(10)···C(6)3.283 (3)H(10A)···H(20A)viii3.437
O(10)···C(19)vi3.570 (3)H(11A)···O(12)2.930
O(10)···C(28)vii3.348 (3)H(11A)···O(13)2.636
O(10)···C(29)vii3.336 (4)H(11A)···C(33)3.580
O(11)···O(4)2.882 (3)H(11A)···C(34)3.455
O(11)···C(7)iv3.479 (3)H(11A)···C(39)3.341
O(11)···C(12)3.527 (4)H(11A)···H(30)3.242
O(11)···C(40)viii2.903 (4)H(11A)···H(39B)3.025
O(12)···O(4)3.301 (3)H(11A)···H(10)3.556
O(13)···C(11)3.572 (3)H(11A)···H(11)3.286
O(13)···C(18)3.571 (4)H(30)···C(1)3.265
C(1)···C(25)ii3.553 (4)H(30)···C(4)3.390
C(2)···O(9)ii3.436 (3)H(30)···C(5)2.866
C(2)···C(24)ii3.517 (4)H(30)···C(6)2.794
C(3)···O(9)ii3.569 (3)H(30)···H(5)3.122
C(3)···C(28)ii3.442 (4)H(30)···H(6)3.013
C(5)···O(10)3.387 (3)H(30)···H(11A)3.242
C(5)···C(21)3.582 (4)H(30)···H(12B)3.238
C(5)···C(30)3.407 (3)H(31)···O(5)vi3.463
C(6)···O(10)3.283 (3)H(31)···O(6)vi2.580
C(6)···C(30)3.465 (4)H(31)···C(14)vi3.576
C(7)···O(4)viii3.558 (4)H(31)···C(19)vi3.101
C(7)···O(9)ii3.588 (4)H(31)···H(10A)vi3.440
C(7)···O(11)viii3.479 (3)H(31)···H(19B)vi2.667
C(8)···O(3)iii3.459 (3)H(8A)···C(21)3.132
C(8)···C(23)3.513 (4)H(8A)···C(22)2.973
C(9)···O(3)iii3.429 (4)H(8A)···C(23)2.889
C(10)···C(25)ii3.492 (3)H(8A)···C(24)2.944
C(10)···C(26)ii3.566 (4)H(8A)···C(25)3.101
C(11)···O(13)3.572 (3)H(8A)···C(25)vii3.486
C(12)···O(11)3.527 (4)H(8A)···C(26)3.186
C(16)···O(1)ix3.335 (3)H(8A)···H(22)3.464
C(18)···O(13)3.571 (4)H(8A)···H(25)vii2.663
C(19)···O(10)ii3.570 (3)H(8A)···H(26)vii3.542
C(19)···C(33)ii3.536 (4)H(8B)···O(3)iii2.738
C(21)···C(5)3.582 (4)H(8B)···C(1)iii3.562
C(22)···O(2)3.548 (3)H(8B)···C(6)iii3.006
C(23)···C(8)3.513 (4)H(8B)···C(25)vii3.596
C(24)···C(2)vi3.517 (4)H(8B)···H(6)iii2.573
C(25)···O(3)vi3.444 (3)H(8B)···H(25)vii2.787
C(25)···C(1)vi3.553 (4)H(8B)···H(3)iii3.275
C(25)···C(10)vi3.492 (3)H(8B)···H(29B)ii3.283
C(26)···O(3)vi3.328 (3)H(12A)···C(20)viii3.100
C(26)···C(10)vi3.566 (4)H(12A)···C(27)v3.362
C(27)···O(4)x3.475 (4)H(12A)···H(20A)viii2.917
C(28)···O(10)vii3.348 (3)H(12A)···H(20B)viii3.100
C(28)···C(3)vi3.442 (4)H(12A)···H(20C)viii2.764
C(29)···O(1)vi3.598 (4)H(12A)···H(27B)v2.414
C(29)···O(10)vii3.336 (4)H(12A)···H(40A)viii3.529
C(30)···C(5)3.407 (3)H(12B)···O(11)3.115
C(30)···C(6)3.465 (4)H(12B)···C(40)viii3.341
C(31)···O(6)vi3.540 (3)H(12B)···H(30)3.238
C(33)···C(19)vi3.536 (4)H(12B)···H(20B)viii3.408
C(36)···O(8)ix3.422 (3)H(12B)···H(40A)viii2.438
C(38)···O(6)vi3.513 (4)H(12B)···H(40C)viii3.556
C(40)···O(11)iv2.903 (4)H(12B)···H(11)2.490
O(1)···H(16)i2.614H(28A)···O(1)vi3.506
O(1)···H(28A)ii3.506H(28A)···C(1)vi3.189
O(1)···H(27A)3.367H(28A)···C(2)vi2.950
O(1)···H(29C)ii2.975H(28A)···C(3)vi2.829
O(2)···H(16)i2.862H(28A)···C(4)vi2.918
O(2)···H(22)3.523H(28A)···C(5)vi3.129
O(2)···H(27A)3.090H(28A)···C(5)vii3.471
O(2)···H(29B)ii3.152H(28A)···C(6)vi3.256
O(3)···H(25)ii3.241H(28A)···H(2)vi3.419
O(3)···H(26)ii3.030H(28A)···H(5)vii2.643
O(3)···H(8B)iii2.738H(28A)···H(6)vii3.547
O(3)···H(39B)2.753H(28B)···O(10)vii2.656
O(3)···H(9A)iii2.949H(28B)···C(26)vii3.025
O(3)···H(9B)iii3.423H(28B)···H(5)vii2.877
O(4)···H(37)viii3.219H(28B)···H(26)vii2.541
O(4)···H(7A)iv3.339H(28B)···H(9B)3.053
O(4)···H(7B)iv3.299H(28B)···H(10)vii3.176
O(4)···H(7C)iv3.451H(32A)···C(20)x3.448
O(4)···H(27B)v2.652H(32A)···H(10A)vi3.367
O(4)···H(40A)viii3.388H(32A)···H(7B)iv3.483
O(4)···H(11)2.191H(32A)···H(20A)x2.576
O(5)···H(31)ii3.463H(32B)···C(7)iv3.143
O(5)···H(27B)v3.389H(32B)···H(7B)iv2.282
O(5)···H(40B)ii3.390H(32B)···H(7C)iv3.322
O(6)···H(26)ii3.512H(7A)···O(4)viii3.339
O(6)···H(31)ii2.580H(7A)···O(8)ii3.240
O(6)···H(39B)3.478H(7A)···O(9)ii2.905
O(7)···H(27B)v3.464H(7A)···C(29)ii3.560
O(7)···H(27C)v3.462H(7A)···C(37)xi3.496
O(8)···H(36)i2.694H(7A)···H(16)i3.397
O(8)···H(7A)vi3.240H(7A)···H(36)xi3.243
O(8)···H(9C)3.092H(7A)···H(37)xi2.747
O(8)···H(4)x2.966H(7A)···H(20B)viii3.527
O(9)···H(2)vi3.363H(7A)···H(29C)ii2.753
O(9)···H(36)i2.851H(7A)···H(4)viii3.169
O(9)···H(7A)vi2.905H(7B)···O(4)viii3.299
O(9)···H(9B)3.076H(7B)···O(11)viii2.589
O(10)···H(5)3.152H(7B)···O(14)viii3.437
O(10)···H(6)2.962H(7B)···C(16)i3.585
O(10)···H(28B)vii2.656H(7B)···C(32)viii2.867
O(10)···H(19B)vi2.663H(7B)···H(16)i3.325
O(10)···H(29A)vii2.935H(7B)···H(37)xi3.303
O(10)···H(29B)vii3.264H(7B)···H(32A)viii3.483
O(11)···H(37)viii3.525H(7B)···H(32B)viii2.282
O(11)···H(12B)3.115H(7B)···H(20B)viii3.426
O(11)···H(7B)iv2.589H(7B)···H(40C)xi3.503
O(11)···H(40A)viii2.632H(7B)···H(4)viii3.473
O(11)···H(40B)viii3.094H(7B)···H(11)viii2.764
O(11)···H(40C)viii2.526H(7C)···O(4)viii3.451
O(11)···H(4)3.577H(7C)···O(14)viii3.375
O(12)···H(11A)2.930H(7C)···C(20)viii3.168
O(12)···H(19B)vi3.501H(7C)···H(32B)viii3.322
O(12)···H(20B)3.507H(7C)···H(20A)viii3.352
O(13)···H(6)3.419H(7C)···H(20B)viii2.288
O(13)···H(11A)2.636H(7C)···H(40A)viii3.192
O(13)···H(19B)vi3.439H(7C)···H(4)viii3.309
O(13)···H(3)3.596H(19A)···C(9)iii3.075
O(13)···H(29A)vii3.574H(19A)···H(26)ii3.512
O(14)···H(7B)iv3.437H(19A)···H(35)xii2.994
O(14)···H(7C)iv3.375H(19A)···H(39A)xii3.414
O(14)···H(20B)3.285H(19A)···H(9A)iii2.629
C(1)···H(25)ii3.353H(19A)···H(9B)iii2.707
C(1)···H(30)3.265H(19A)···H(9C)iii3.496
C(1)···H(8B)iii3.562H(19B)···O(10)ii2.663
C(1)···H(28A)ii3.189H(19B)···O(12)ii3.501
C(2)···H(28A)ii2.950H(19B)···O(13)ii3.439
C(2)···H(40A)viii3.469H(19B)···C(30)ii3.479
C(3)···H(28A)ii2.829H(19B)···C(31)ii3.295
C(3)···H(40A)viii3.542H(19B)···C(33)ii3.001
C(3)···H(29B)ii3.600H(19B)···C(34)ii3.026
C(3)···H(29C)ii3.371H(19B)···C(35)ii3.505
C(4)···H(22)3.434H(19B)···C(38)ii3.460
C(4)···H(30)3.390H(19B)···H(26)ii3.107
C(4)···H(28A)ii2.918H(19B)···H(31)ii2.667
C(4)···H(29B)ii3.328H(19B)···H(9B)iii3.485
C(5)···H(5)iii3.450H(19B)···H(29A)iii3.110
C(5)···H(30)2.866H(19B)···H(10)ii2.267
C(5)···H(28A)ii3.129H(19C)···C(33)ii3.460
C(5)···H(28A)vii3.471H(19C)···C(34)ii3.422
C(6)···H(5)iii3.586H(19C)···C(35)ii3.292
C(6)···H(30)2.794H(19C)···C(36)ii3.188
C(6)···H(8B)iii3.006H(19C)···C(37)ii3.242
C(6)···H(28A)ii3.256H(19C)···C(38)ii3.368
C(7)···H(16)i3.345H(19C)···H(39A)xii3.521
C(7)···H(37)xi3.456H(19C)···H(29A)xiii3.467
C(7)···H(32B)viii3.143H(19C)···H(29C)xiii3.583
C(7)···H(20B)viii3.180H(20A)···C(22)v3.586
C(7)···H(29C)ii3.327H(20A)···C(32)v3.475
C(7)···H(4)viii3.507H(20A)···H(2)iv3.099
C(7)···H(11)viii3.543H(20A)···H(22)v3.545
C(8)···H(6)iii3.512H(20A)···H(10A)iv3.437
C(8)···H(25)vii3.128H(20A)···H(12A)iv2.917
C(9)···H(16)i3.577H(20A)···H(32A)v2.576
C(9)···H(26)vii3.540H(20A)···H(7C)iv3.352
C(9)···H(35)i2.957H(20A)···H(27C)v3.468
C(9)···H(36)i3.436H(20B)···O(12)3.507
C(9)···H(19A)iii3.075H(20B)···O(14)3.285
C(9)···H(3)iii3.558H(20B)···C(7)iv3.180
C(10)···H(25)ii3.501H(20B)···C(33)3.323
C(11)···H(11)3.596H(20B)···C(38)3.206
C(12)···H(27B)v2.958H(20B)···H(2)iv2.769
C(12)···H(40A)viii3.224H(20B)···H(12A)iv3.100
C(12)···H(11)2.800H(20B)···H(12B)iv3.408
C(13)···H(39B)3.255H(20B)···H(7A)iv3.527
C(13)···H(39C)3.511H(20B)···H(7B)iv3.426
C(13)···H(40B)ii3.412H(20B)···H(7C)iv2.288
C(13)···H(40C)ii3.421H(20B)···H(40A)3.494
C(14)···H(31)ii3.576H(20C)···C(33)3.423
C(14)···H(39B)3.112H(20C)···C(34)3.543
C(14)···H(39C)3.390H(20C)···C(35)3.590
C(14)···H(40C)ii3.410H(20C)···C(36)3.510
C(15)···H(37)ii3.567H(20C)···C(37)3.387
C(15)···H(39A)xii3.568H(20C)···C(38)3.339
C(15)···H(39B)3.497H(20C)···H(12A)iv2.764
C(15)···H(39C)3.208H(20C)···H(27A)ix3.494
C(15)···H(40C)ii3.578H(20C)···H(27B)ix3.248
C(15)···H(29C)xiii3.119H(27A)···O(1)3.367
C(16)···H(7B)ix3.585H(27A)···O(2)3.090
C(16)···H(39C)3.132H(27A)···C(17)i3.452
C(16)···H(9C)ix3.596H(27A)···H(16)i3.366
C(16)···H(29C)xiii3.267H(27A)···H(17)i2.649
C(17)···H(27A)ix3.452H(27A)···H(36)i3.413
C(17)···H(39C)3.279H(27A)···H(20C)i3.494
C(18)···H(39C)3.469H(27A)···H(40B)viii3.226
C(18)···H(40C)ii3.562H(27A)···H(9C)2.892
C(19)···H(26)ii3.547H(27A)···H(4)x3.485
C(19)···H(31)ii3.101H(27B)···O(4)x2.652
C(19)···H(9A)iii3.478H(27B)···O(5)x3.389
C(19)···H(9B)iii3.456H(27B)···O(7)x3.464
C(19)···H(10)ii3.212H(27B)···C(12)x2.958
C(20)···H(2)iv3.366H(27B)···H(17)i3.298
C(20)···H(12A)iv3.100H(27B)···H(36)i3.452
C(20)···H(32A)v3.448H(27B)···H(12A)x2.414
C(20)···H(7C)iv3.168H(27B)···H(20C)i3.248
C(21)···H(5)3.386H(27B)···H(40B)viii3.214
C(21)···H(10A)vi3.378H(27B)···H(4)x1.947
C(21)···H(8A)3.132H(27C)···O(7)x3.462
C(22)···H(8A)2.973H(27C)···C(40)viii3.127
C(22)···H(20A)x3.586H(27C)···H(20A)x3.468
C(23)···H(8A)2.889H(27C)···H(40A)viii3.340
C(23)···H(9B)3.586H(27C)···H(40B)viii2.220
C(23)···H(9C)3.401H(27C)···H(40C)viii3.593
C(24)···H(2)vi3.288H(27C)···H(4)x3.016
C(24)···H(10A)vi3.491H(39A)···C(15)xii3.568
C(24)···H(8A)2.944H(39A)···C(29)vii3.106
C(24)···H(9B)3.245H(39A)···H(15)xii2.902
C(25)···H(25)vii3.522H(39A)···H(19A)xii3.414
C(25)···H(10A)vi3.021H(39A)···H(19C)xii3.521
C(25)···H(8A)3.101H(39A)···H(29A)vii2.758
C(25)···H(8A)vii3.486H(39A)···H(29B)vii2.682
C(25)···H(8B)vii3.596H(39A)···H(29C)vii3.441
C(26)···H(10A)vi2.958H(39B)···O(3)2.753
C(26)···H(8A)3.186H(39B)···O(6)3.478
C(26)···H(28B)vii3.025H(39B)···C(13)3.255
C(27)···H(17)i3.393H(39B)···C(14)3.112
C(27)···H(36)i3.422H(39B)···C(15)3.497
C(27)···H(12A)x3.362H(39B)···H(6)3.192
C(27)···H(40B)viii3.012H(39B)···H(11A)3.025
C(27)···H(9C)3.468H(39B)···H(9A)iii2.931
C(27)···H(4)x2.703H(39B)···H(3)2.344
C(28)···H(5)vii3.165H(39B)···H(29B)vii3.328
C(28)···H(26)vii3.495H(39C)···C(13)3.511
C(28)···H(9B)3.495H(39C)···C(14)3.390
C(29)···H(15)xiv3.039H(39C)···C(15)3.208
C(29)···H(16)xiv3.449H(39C)···C(16)3.132
C(29)···H(36)i3.494H(39C)···C(17)3.279
C(29)···H(7A)vi3.560H(39C)···C(18)3.469
C(29)···H(39A)vii3.106H(39C)···H(16)3.507
C(29)···H(10)vii3.415H(39C)···H(9A)ix3.406
C(30)···H(5)3.407H(39C)···H(9C)ix3.575
C(30)···H(6)3.502H(40A)···O(4)iv3.388
C(30)···H(19B)vi3.479H(40A)···O(11)iv2.632
C(31)···H(19B)vi3.295H(40A)···C(2)iv3.469
C(32)···H(7B)iv2.867H(40A)···C(3)iv3.542
C(32)···H(20A)x3.475H(40A)···C(12)iv3.224
C(33)···H(11A)3.580H(40A)···H(2)iv3.379
C(33)···H(19B)vi3.001H(40A)···H(22)iv3.259
C(33)···H(19C)vi3.460H(40A)···H(12A)iv3.529
C(33)···H(20B)3.323H(40A)···H(12B)iv2.438
C(33)···H(20C)3.423H(40A)···H(7C)iv3.192
C(34)···H(11A)3.455H(40A)···H(20B)3.494
C(34)···H(19B)vi3.026H(40A)···H(27C)iv3.340
C(34)···H(19C)vi3.422H(40A)···H(11)iv2.679
C(34)···H(20C)3.543H(40B)···O(5)vi3.390
C(35)···H(17)3.497H(40B)···O(11)iv3.094
C(35)···H(19B)vi3.505H(40B)···C(13)vi3.412
C(35)···H(19C)vi3.292H(40B)···C(27)iv3.012
C(35)···H(20C)3.590H(40B)···H(22)iv2.937
C(35)···H(9C)ix3.061H(40B)···H(27A)iv3.226
C(36)···H(19C)vi3.188H(40B)···H(27B)iv3.214
C(36)···H(20C)3.510H(40B)···H(27C)iv2.220
C(36)···H(9C)ix3.235H(40B)···H(11)iv3.514
C(36)···H(29C)ix3.553H(40C)···O(11)iv2.526
C(37)···H(15)vi3.584H(40C)···C(13)vi3.421
C(37)···H(7A)xv3.496H(40C)···C(14)vi3.410
C(37)···H(19C)vi3.242H(40C)···C(15)vi3.578
C(37)···H(20C)3.387H(40C)···C(18)vi3.562
C(38)···H(19B)vi3.460H(40C)···H(12B)iv3.556
C(38)···H(19C)vi3.368H(40C)···H(7B)xv3.503
C(38)···H(20B)3.206H(40C)···H(27C)iv3.593
C(38)···H(20C)3.339H(40C)···H(11)iv2.880
C(39)···H(11A)3.341H(9A)···O(3)iii2.949
C(39)···H(3)3.232H(9A)···C(19)iii3.478
C(39)···H(29A)vii3.523H(9A)···H(16)i3.466
C(39)···H(29B)vii3.326H(9A)···H(35)i2.871
C(40)···H(22)iv3.491H(9A)···H(19A)iii2.629
C(40)···H(12B)iv3.341H(9A)···H(39B)iii2.931
C(40)···H(27C)iv3.127H(9A)···H(39C)i3.406
C(40)···H(11)iv3.170H(9A)···H(3)iii2.923
H(2)···O(9)ii3.363H(9B)···O(3)iii3.423
H(2)···C(20)viii3.366H(9B)···O(9)3.076
H(2)···C(24)ii3.288H(9B)···C(19)iii3.456
H(2)···H(28A)ii3.419H(9B)···C(23)3.586
H(2)···H(20A)viii3.099H(9B)···C(24)3.245
H(2)···H(20B)viii2.769H(9B)···C(28)3.495
H(2)···H(40A)viii3.379H(9B)···H(25)vii3.509
H(5)···O(10)3.152H(9B)···H(26)vii2.788
H(5)···C(5)iii3.450H(9B)···H(35)i3.094
H(5)···C(6)iii3.586H(9B)···H(36)i3.232
H(5)···C(21)3.386H(9B)···H(28B)3.053
H(5)···C(28)vii3.165H(9B)···H(19A)iii2.707
H(5)···C(30)3.407H(9B)···H(19B)iii3.485
H(5)···H(5)iii3.389H(9B)···H(3)iii3.536
H(5)···H(25)vii3.151H(9B)···H(29A)3.600
H(5)···H(30)3.122H(9C)···O(8)3.092
H(5)···H(28A)vii2.643H(9C)···C(16)i3.596
H(5)···H(28B)vii2.877H(9C)···C(23)3.401
H(5)···H(29B)vii3.552H(9C)···C(27)3.468
H(6)···O(10)2.962H(9C)···C(35)i3.061
H(6)···O(13)3.419H(9C)···C(36)i3.235
H(6)···C(8)iii3.512H(9C)···H(16)i3.067
H(6)···C(30)3.502H(9C)···H(17)i3.593
H(6)···H(30)3.013H(9C)···H(35)i2.441
H(6)···H(8B)iii2.573H(9C)···H(36)i2.777
H(6)···H(28A)vii3.547H(9C)···H(19A)iii3.496
H(6)···H(39B)3.192H(9C)···H(27A)2.892
H(6)···H(29B)vii2.865H(9C)···H(39C)i3.575
H(6)···H(10)3.168H(3)···O(13)3.596
H(15)···C(29)xiii3.039H(3)···C(9)iii3.558
H(15)···C(37)ii3.584H(3)···C(39)3.232
H(15)···H(37)ii3.545H(3)···H(26)ii3.300
H(15)···H(39A)xii2.902H(3)···H(8B)iii3.275
H(15)···H(29A)xiii2.991H(3)···H(39B)2.344
H(15)···H(29B)xiii3.171H(3)···H(9A)iii2.923
H(15)···H(29C)xiii2.486H(3)···H(9B)iii3.536
H(16)···O(1)ix2.614H(29A)···O(10)vii2.935
H(16)···O(2)ix2.862H(29A)···O(13)vii3.574
H(16)···C(7)ix3.345H(29A)···C(39)vii3.523
H(16)···C(9)ix3.577H(29A)···H(15)xiv2.991
H(16)···C(29)xiii3.449H(29A)···H(36)i3.341
H(16)···H(7A)ix3.397H(29A)···H(19B)iii3.110
H(16)···H(7B)ix3.325H(29A)···H(19C)xiv3.467
H(16)···H(27A)ix3.366H(29A)···H(39A)vii2.758
H(16)···H(39C)3.507H(29A)···H(9B)3.600
H(16)···H(9A)ix3.466H(29A)···H(10)vii2.863
H(16)···H(9C)ix3.067H(29B)···O(2)vi3.152
H(16)···H(29B)xiii3.241H(29B)···O(10)vii3.264
H(16)···H(29C)xiii2.788H(29B)···C(3)vi3.600
H(17)···C(27)ix3.393H(29B)···C(4)vi3.328
H(17)···C(35)3.497H(29B)···C(39)vii3.326
H(17)···H(35)3.577H(29B)···H(5)vii3.552
H(17)···H(27A)ix2.649H(29B)···H(6)vii2.865
H(17)···H(27B)ix3.298H(29B)···H(15)xiv3.171
H(17)···H(9C)ix3.593H(29B)···H(16)xiv3.241
H(22)···O(2)3.523H(29B)···H(8B)vi3.283
H(22)···C(4)3.434H(29B)···H(39A)vii2.682
H(22)···C(40)viii3.491H(29B)···H(39B)vii3.328
H(22)···H(8A)3.464H(29B)···H(10)vii3.306
H(22)···H(20A)x3.545H(29C)···O(1)vi2.975
H(22)···H(40A)viii3.259H(29C)···C(3)vi3.371
H(22)···H(40B)viii2.937H(29C)···C(7)vi3.327
H(25)···O(3)vi3.241H(29C)···C(15)xiv3.119
H(25)···C(1)vi3.353H(29C)···C(16)xiv3.267
H(25)···C(8)vii3.128H(29C)···C(36)i3.553
H(25)···C(10)vi3.501H(29C)···H(15)xiv2.486
H(25)···C(25)vii3.522H(29C)···H(16)xiv2.788
H(25)···H(5)vii3.151H(29C)···H(36)i3.017
H(25)···H(25)vii3.456H(29C)···H(7A)vi2.753
H(25)···H(26)vii3.597H(29C)···H(19C)xiv3.583
H(25)···H(10A)vi3.284H(29C)···H(39A)vii3.441
H(25)···H(8A)vii2.663H(4)···O(8)v2.966
H(25)···H(8B)vii2.787H(4)···O(11)3.577
H(25)···H(9B)vii3.509H(4)···C(7)iv3.507
H(26)···O(3)vi3.030H(4)···C(27)v2.703
H(26)···O(6)vi3.512H(4)···H(37)viii3.289
H(26)···C(9)vii3.540H(4)···H(7A)iv3.169
H(26)···C(19)vi3.547H(4)···H(7B)iv3.473
H(26)···C(28)vii3.495H(4)···H(7C)iv3.309
H(26)···H(25)vii3.597H(4)···H(27A)v3.485
H(26)···H(10A)vi3.187H(4)···H(27B)v1.947
H(26)···H(8A)vii3.542H(4)···H(27C)v3.016
H(26)···H(28B)vii2.541H(4)···H(11)2.938
H(26)···H(19A)vi3.512H(10)···C(19)vi3.212
H(26)···H(19B)vi3.107H(10)···C(29)vii3.415
H(26)···H(9B)vii2.788H(10)···H(6)3.168
H(26)···H(3)vi3.300H(10)···H(11A)3.556
H(35)···C(9)ix2.957H(10)···H(28B)vii3.176
H(35)···H(17)3.577H(10)···H(19B)vi2.267
H(35)···H(19A)xii2.994H(10)···H(29A)vii2.863
H(35)···H(9A)ix2.871H(10)···H(29B)vii3.306
H(35)···H(9B)ix3.094H(11)···O(4)2.191
H(35)···H(9C)ix2.441H(11)···C(7)iv3.543
H(36)···O(8)ix2.694H(11)···C(11)3.596
H(36)···O(9)ix2.851H(11)···C(12)2.800
H(36)···C(9)ix3.436H(11)···C(40)viii3.170
H(36)···C(27)ix3.422H(11)···H(37)viii3.558
H(36)···C(29)ix3.494H(11)···H(11A)3.286
H(36)···H(7A)xv3.243H(11)···H(12B)2.490
H(36)···H(27A)ix3.413H(11)···H(7B)iv2.764
H(36)···H(27B)ix3.452H(11)···H(40A)viii2.679
H(36)···H(9B)ix3.232H(11)···H(40B)viii3.514
H(36)···H(9C)ix2.777H(11)···H(40C)viii2.880
H(36)···H(29A)ix3.341H(11)···H(4)2.938
C(3)—O(1)—C(7)117.5 (2)O(2)—C(8)—H(8B)110.0
C(4)—O(2)—C(8)117.0 (2)C(9)—C(8)—H(8A)110.0
C(11)—O(5)—C(13)119.1 (2)C(9)—C(8)—H(8B)110.1
C(14)—O(6)—C(19)117.8 (2)H(8A)—C(8)—H(8B)109.5
C(18)—O(7)—C(20)117.9 (2)C(8)—C(9)—H(9A)109.4
C(23)—O(8)—C(27)117.1 (2)C(8)—C(9)—H(9B)109.5
C(24)—O(9)—C(28)116.8 (2)C(8)—C(9)—H(9C)109.4
C(31)—O(12)—C(33)117.9 (2)H(9A)—C(9)—H(9B)109.5
C(34)—O(13)—C(39)118.4 (2)H(9A)—C(9)—H(9C)109.5
C(38)—O(14)—C(40)117.4 (2)H(9B)—C(9)—H(9C)109.5
C(2)—C(1)—C(6)118.5 (2)O(3)—C(10)—H(10A)109.0
C(2)—C(1)—C(10)120.4 (2)C(1)—C(10)—H(10A)109.0
C(6)—C(1)—C(10)121.0 (2)C(11)—C(10)—H(10A)109.0
C(1)—C(2)—C(3)121.1 (2)O(5)—C(11)—H(11A)110.3
O(1)—C(3)—C(2)125.4 (2)C(10)—C(11)—H(11A)110.3
O(1)—C(3)—C(4)114.6 (2)C(12)—C(11)—H(11A)110.2
C(2)—C(3)—C(4)119.9 (2)O(4)—C(12)—H(12A)108.8
O(2)—C(4)—C(3)115.9 (2)O(4)—C(12)—H(12B)107.6
O(2)—C(4)—C(5)125.0 (2)C(11)—C(12)—H(12A)108.2
C(3)—C(4)—C(5)119.1 (2)C(11)—C(12)—H(12B)108.3
C(4)—C(5)—C(6)120.4 (2)H(12A)—C(12)—H(12B)109.5
C(1)—C(6)—C(5)120.9 (2)C(14)—C(15)—H(15)120.1
O(2)—C(8)—C(9)107.2 (2)C(16)—C(15)—H(15)120.2
O(3)—C(10)—C(1)107.5 (2)C(15)—C(16)—H(16)119.6
O(3)—C(10)—C(11)109.9 (2)C(17)—C(16)—H(16)119.7
C(1)—C(10)—C(11)112.4 (2)C(16)—C(17)—H(17)120.0
O(5)—C(11)—C(10)106.9 (2)C(18)—C(17)—H(17)120.2
O(5)—C(11)—C(12)106.6 (2)O(6)—C(19)—H(19A)109.5
C(10)—C(11)—C(12)112.5 (2)O(6)—C(19)—H(19B)109.4
O(4)—C(12)—C(11)114.4 (2)O(6)—C(19)—H(19C)109.4
O(5)—C(13)—C(14)119.8 (2)H(19A)—C(19)—H(19B)109.5
O(5)—C(13)—C(18)121.0 (2)H(19A)—C(19)—H(19C)109.5
C(14)—C(13)—C(18)118.8 (2)H(19B)—C(19)—H(19C)109.5
O(6)—C(14)—C(13)116.2 (2)O(7)—C(20)—H(20A)109.5
O(6)—C(14)—C(15)123.5 (2)O(7)—C(20)—H(20B)109.5
C(13)—C(14)—C(15)120.3 (2)O(7)—C(20)—H(20C)109.4
C(14)—C(15)—C(16)119.7 (3)H(20A)—C(20)—H(20B)109.5
C(15)—C(16)—C(17)120.8 (2)H(20A)—C(20)—H(20C)109.5
C(16)—C(17)—C(18)119.8 (2)H(20B)—C(20)—H(20C)109.5
O(7)—C(18)—C(13)115.7 (2)C(21)—C(22)—H(22)119.5
O(7)—C(18)—C(17)123.7 (2)C(23)—C(22)—H(22)119.6
C(13)—C(18)—C(17)120.6 (3)C(24)—C(25)—H(25)120.0
C(22)—C(21)—C(26)118.6 (2)C(26)—C(25)—H(25)119.9
C(22)—C(21)—C(30)120.2 (2)C(21)—C(26)—H(26)119.4
C(26)—C(21)—C(30)121.1 (2)C(25)—C(26)—H(26)119.5
C(21)—C(22)—C(23)120.8 (2)O(8)—C(27)—H(27A)109.4
O(8)—C(23)—C(22)125.2 (2)O(8)—C(27)—H(27B)109.6
O(8)—C(23)—C(24)114.6 (2)O(8)—C(27)—H(27C)109.5
C(22)—C(23)—C(24)120.1 (2)H(27A)—C(27)—H(27B)109.5
O(9)—C(24)—C(23)116.0 (2)H(27A)—C(27)—H(27C)109.5
O(9)—C(24)—C(25)124.8 (2)H(27B)—C(27)—H(27C)109.5
C(23)—C(24)—C(25)119.2 (2)O(9)—C(28)—H(28A)110.1
C(24)—C(25)—C(26)120.1 (2)O(9)—C(28)—H(28B)110.0
C(21)—C(26)—C(25)121.1 (2)C(29)—C(28)—H(28A)110.2
O(9)—C(28)—C(29)107.0 (2)C(29)—C(28)—H(28B)110.0
O(10)—C(30)—C(21)108.3 (2)H(28A)—C(28)—H(28B)109.5
O(10)—C(30)—C(31)109.2 (2)C(28)—C(29)—H(29A)109.6
C(21)—C(30)—C(31)113.6 (2)C(28)—C(29)—H(29B)109.4
O(12)—C(31)—C(30)104.7 (2)C(28)—C(29)—H(29C)109.5
O(12)—C(31)—C(32)107.2 (2)H(29A)—C(29)—H(29B)109.5
C(30)—C(31)—C(32)114.3 (2)H(29A)—C(29)—H(29C)109.5
O(11)—C(32)—C(31)111.5 (2)H(29B)—C(29)—H(29C)109.5
O(12)—C(33)—C(34)118.8 (2)O(10)—C(30)—H(30)108.6
O(12)—C(33)—C(38)121.4 (2)C(21)—C(30)—H(30)108.5
C(34)—C(33)—C(38)119.6 (2)C(31)—C(30)—H(30)108.5
O(13)—C(34)—C(33)115.6 (2)O(12)—C(31)—H(31)110.2
O(13)—C(34)—C(35)124.2 (3)C(30)—C(31)—H(31)110.2
C(33)—C(34)—C(35)120.2 (2)C(32)—C(31)—H(31)110.2
C(34)—C(35)—C(36)119.1 (3)O(11)—C(32)—H(32A)109.0
C(35)—C(36)—C(37)121.7 (3)O(11)—C(32)—H(32B)109.0
C(36)—C(37)—C(38)119.1 (3)C(31)—C(32)—H(32A)108.9
O(14)—C(38)—C(33)114.3 (2)C(31)—C(32)—H(32B)108.9
O(14)—C(38)—C(37)125.4 (3)H(32A)—C(32)—H(32B)109.5
C(33)—C(38)—C(37)120.3 (3)C(34)—C(35)—H(35)120.5
C(10)—O(3)—H(3)109.6C(36)—C(35)—H(35)120.4
C(12)—O(4)—H(4)108.8C(35)—C(36)—H(36)119.2
C(30)—O(10)—H(10)109.5C(37)—C(36)—H(36)119.1
C(32)—O(11)—H(11)109.6C(36)—C(37)—H(37)120.4
C(1)—C(2)—H(2)119.5C(38)—C(37)—H(37)120.5
C(3)—C(2)—H(2)119.4O(13)—C(39)—H(39A)109.3
C(4)—C(5)—H(5)119.8O(13)—C(39)—H(39B)109.6
C(6)—C(5)—H(5)119.8O(13)—C(39)—H(39C)109.5
C(1)—C(6)—H(6)119.5H(39A)—C(39)—H(39B)109.5
C(5)—C(6)—H(6)119.5H(39A)—C(39)—H(39C)109.5
O(1)—C(7)—H(7A)109.4H(39B)—C(39)—H(39C)109.5
O(1)—C(7)—H(7B)109.5O(14)—C(40)—H(40A)109.4
O(1)—C(7)—H(7C)109.5O(14)—C(40)—H(40B)109.6
H(7A)—C(7)—H(7B)109.5O(14)—C(40)—H(40C)109.4
H(7A)—C(7)—H(7C)109.5H(40A)—C(40)—H(40B)109.5
H(7B)—C(7)—H(7C)109.5H(40A)—C(40)—H(40C)109.5
O(2)—C(8)—H(8A)110.0H(40B)—C(40)—H(40C)109.5
C(7)—O(1)—C(3)—C(2)−5.8 (4)O(5)—C(13)—C(14)—C(15)−174.1 (3)
C(7)—O(1)—C(3)—C(4)172.3 (2)O(5)—C(13)—C(18)—O(7)−3.8 (4)
C(4)—O(2)—C(8)—C(9)−179.9 (2)O(5)—C(13)—C(18)—C(17)174.8 (3)
C(8)—O(2)—C(4)—C(3)−177.8 (2)C(14)—C(13)—C(18)—O(7)−176.3 (3)
C(8)—O(2)—C(4)—C(5)2.3 (3)C(14)—C(13)—C(18)—C(17)2.2 (5)
C(11)—O(5)—C(13)—C(14)−109.4 (3)C(18)—C(13)—C(14)—O(6)177.5 (2)
C(11)—O(5)—C(13)—C(18)78.1 (3)C(18)—C(13)—C(14)—C(15)−1.4 (5)
C(13)—O(5)—C(11)—C(10)107.7 (2)O(6)—C(14)—C(15)—C(16)−179.4 (3)
C(13)—O(5)—C(11)—C(12)−131.8 (2)C(13)—C(14)—C(15)—C(16)−0.5 (5)
C(19)—O(6)—C(14)—C(13)178.1 (2)C(14)—C(15)—C(16)—C(17)1.8 (5)
C(19)—O(6)—C(14)—C(15)−3.0 (4)C(15)—C(16)—C(17)—C(18)−1.0 (5)
C(20)—O(7)—C(18)—C(13)175.9 (3)C(16)—C(17)—C(18)—O(7)177.4 (3)
C(20)—O(7)—C(18)—C(17)−2.7 (5)C(16)—C(17)—C(18)—C(13)−1.1 (5)
C(27)—O(8)—C(23)—C(22)−7.1 (4)C(22)—C(21)—C(26)—C(25)−0.5 (4)
C(27)—O(8)—C(23)—C(24)171.0 (2)C(26)—C(21)—C(22)—C(23)0.1 (3)
C(24)—O(9)—C(28)—C(29)177.8 (2)C(22)—C(21)—C(30)—O(10)150.0 (2)
C(28)—O(9)—C(24)—C(23)−175.0 (2)C(22)—C(21)—C(30)—C(31)−88.5 (3)
C(28)—O(9)—C(24)—C(25)4.3 (3)C(30)—C(21)—C(22)—C(23)−177.6 (2)
C(31)—O(12)—C(33)—C(34)−118.3 (3)C(26)—C(21)—C(30)—O(10)−27.7 (3)
C(31)—O(12)—C(33)—C(38)66.7 (3)C(26)—C(21)—C(30)—C(31)93.8 (3)
C(33)—O(12)—C(31)—C(30)115.3 (2)C(30)—C(21)—C(26)—C(25)177.2 (2)
C(33)—O(12)—C(31)—C(32)−123.0 (2)C(21)—C(22)—C(23)—O(8)178.9 (2)
C(39)—O(13)—C(34)—C(33)−175.5 (2)C(21)—C(22)—C(23)—C(24)0.9 (4)
C(39)—O(13)—C(34)—C(35)4.6 (4)O(8)—C(23)—C(24)—O(9)−0.3 (3)
C(40)—O(14)—C(38)—C(33)178.1 (3)O(8)—C(23)—C(24)—C(25)−179.7 (2)
C(40)—O(14)—C(38)—C(37)0.8 (5)C(22)—C(23)—C(24)—O(9)177.8 (2)
C(2)—C(1)—C(6)—C(5)0.6 (4)C(22)—C(23)—C(24)—C(25)−1.5 (4)
C(6)—C(1)—C(2)—C(3)−1.4 (4)O(9)—C(24)—C(25)—C(26)−178.2 (2)
C(2)—C(1)—C(10)—O(3)147.5 (2)C(23)—C(24)—C(25)—C(26)1.1 (4)
C(2)—C(1)—C(10)—C(11)−91.4 (3)C(24)—C(25)—C(26)—C(21)−0.1 (3)
C(10)—C(1)—C(2)—C(3)178.2 (2)O(10)—C(30)—C(31)—O(12)−60.8 (2)
C(6)—C(1)—C(10)—O(3)−32.9 (3)O(10)—C(30)—C(31)—C(32)−177.7 (2)
C(6)—C(1)—C(10)—C(11)88.2 (3)C(21)—C(30)—C(31)—O(12)178.2 (2)
C(10)—C(1)—C(6)—C(5)−179.0 (2)C(21)—C(30)—C(31)—C(32)61.3 (3)
C(1)—C(2)—C(3)—O(1)179.5 (2)O(12)—C(31)—C(32)—O(11)−57.1 (2)
C(1)—C(2)—C(3)—C(4)1.5 (4)C(30)—C(31)—C(32)—O(11)58.4 (3)
O(1)—C(3)—C(4)—O(2)1.0 (3)O(12)—C(33)—C(34)—O(13)4.8 (4)
O(1)—C(3)—C(4)—C(5)−179.0 (2)O(12)—C(33)—C(34)—C(35)−175.3 (3)
C(2)—C(3)—C(4)—O(2)179.2 (2)O(12)—C(33)—C(38)—O(14)−2.5 (4)
C(2)—C(3)—C(4)—C(5)−0.9 (4)O(12)—C(33)—C(38)—C(37)175.0 (3)
O(2)—C(4)—C(5)—C(6)−179.9 (2)C(34)—C(33)—C(38)—O(14)−177.5 (3)
C(3)—C(4)—C(5)—C(6)0.1 (3)C(34)—C(33)—C(38)—C(37)0.0 (4)
C(4)—C(5)—C(6)—C(1)0.0 (3)C(38)—C(33)—C(34)—O(13)180.0 (2)
O(3)—C(10)—C(11)—O(5)−64.6 (2)C(38)—C(33)—C(34)—C(35)−0.2 (4)
O(3)—C(10)—C(11)—C(12)178.7 (2)O(13)—C(34)—C(35)—C(36)179.7 (3)
C(1)—C(10)—C(11)—O(5)175.7 (2)C(33)—C(34)—C(35)—C(36)−0.1 (4)
C(1)—C(10)—C(11)—C(12)59.1 (3)C(34)—C(35)—C(36)—C(37)0.6 (5)
O(5)—C(11)—C(12)—O(4)78.0 (3)C(35)—C(36)—C(37)—C(38)−0.7 (6)
C(10)—C(11)—C(12)—O(4)−165.1 (2)C(36)—C(37)—C(38)—O(14)177.6 (3)
O(5)—C(13)—C(14)—O(6)4.8 (4)C(36)—C(37)—C(38)—C(33)0.4 (5)

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) −x+1, −y, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2; (vi) x+1, y, z; (vii) −x+2, −y, −z+1; (viii) x−1/2, −y+1/2, z−1/2; (ix) x, y, z+1; (x) x+1/2, −y+1/2, z−1/2; (xi) x−1, y, z−1; (xii) −x+1, −y, −z+2; (xiii) x−1, y, z+1; (xiv) x+1, y, z−1; (xv) x+1, y, z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O60.8192.0892.772 (3)140.7
O4—H4···O70.8212.4612.758 (3)102.5
O10—H10···O130.8202.1652.878 (3)145.4
O11—H11···O40.8202.1912.882 (3)142.1
O3—H3···O50.8202.442.859 (3)113
O10—H10···O120.8202.322.760 (3)114
O11—H11···O120.8202.362.795 (3)114
.—···......

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2203).

References

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