The asymmetric unit of the title compound, C
40H
26O
4·-2(CH
3)
2CO, consists of one molecule of (
R,
R)-3,3′-bisBINOL [(
R,
R)-1,1′:3′,3′′:1′′,1′′′-quater-2-naphthol] and two acetone molecules. The central feature of the structure is the pair of unique sets of O—H
O
H—O hydrogen-bond arrangements between the two hydroxy groups of (
R,
R)-3,3′-bisBINOL and the O atom of acetone, which fixes the axial chirality of the 3,3′-bond as
S, thus maintaining the helical structure of the bisBINOL in the
M form.
Supporting information
CCDC reference: 232162
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.100
- Data-to-parameter ratio = 9.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.47
From the CIF: _reflns_number_total 4540
Count of symmetry unique reflns 4572
Completeness (_total/calc) 99.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C40H26O4·2C3H6O | F(000) = 1448 |
Mr = 686.76 | Dx = 1.268 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 38232 reflections |
a = 13.403 (2) Å | θ = 3.0–27.5° |
b = 15.5692 (10) Å | µ = 0.08 mm−1 |
c = 17.235 (2) Å | T = 93 K |
V = 3596.5 (7) Å3 | Block, colorless |
Z = 4 | 0.60 × 0.55 × 0.50 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4366 reflections with I > 2σ(I) |
ω scans | Rint = 0.050 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | θmax = 27.5°, θmin = 3.0° |
Tmin = 0.952, Tmax = 0.968 | h = −17→17 |
31216 measured reflections | k = −20→20 |
4540 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0455P)2 + 1.2636P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.100 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.21 e Å−3 |
4540 reflections | Δρmin = −0.19 e Å−3 |
489 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.08777 (13) | 0.01546 (11) | 0.65147 (9) | 0.0329 (3) | |
O2 | 0.06346 (12) | 0.02066 (10) | 0.81031 (10) | 0.0298 (3) | |
O3 | 0.22721 (12) | 0.10109 (10) | 0.70258 (9) | 0.0290 (3) | |
O4 | 0.39041 (12) | −0.05410 (10) | 0.77821 (10) | 0.0305 (3) | |
O5 | 0.04114 (12) | 0.16047 (11) | 0.63711 (9) | 0.0329 (4) | |
O6 | 0.24774 (13) | −0.01320 (11) | 0.89128 (9) | 0.0332 (3) | |
C1 | −0.14239 (15) | 0.03622 (13) | 0.78424 (12) | 0.0245 (4) | |
C2 | −0.14680 (16) | −0.00515 (14) | 0.71339 (12) | 0.0271 (4) | |
C3 | −0.21574 (17) | −0.07256 (14) | 0.70040 (14) | 0.0316 (5) | |
H5 | −0.2172 | −0.1005 | 0.6514 | 0.038* | |
C4 | −0.27996 (17) | −0.09787 (15) | 0.75726 (14) | 0.0319 (5) | |
H6 | −0.3251 | −0.1437 | 0.7476 | 0.038* | |
C5 | −0.28040 (16) | −0.05662 (14) | 0.83083 (13) | 0.0285 (4) | |
C6 | −0.34890 (17) | −0.07952 (16) | 0.88987 (14) | 0.0343 (5) | |
H7 | −0.3951 | −0.1247 | 0.8809 | 0.041* | |
C7 | −0.34958 (18) | −0.03749 (16) | 0.95971 (14) | 0.0358 (5) | |
H8 | −0.3966 | −0.0527 | 0.9986 | 0.043* | |
C8 | −0.27996 (17) | 0.02841 (16) | 0.97325 (14) | 0.0329 (5) | |
H9 | −0.2804 | 0.0576 | 1.0216 | 0.039* | |
C9 | −0.21128 (17) | 0.05136 (14) | 0.91781 (13) | 0.0283 (4) | |
H10 | −0.1640 | 0.0951 | 0.9289 | 0.034* | |
C10 | −0.21001 (15) | 0.01047 (13) | 0.84413 (13) | 0.0254 (4) | |
C11 | −0.07562 (15) | 0.11183 (13) | 0.79580 (12) | 0.0243 (4) | |
C12 | 0.02620 (15) | 0.10253 (13) | 0.80782 (11) | 0.0242 (4) | |
C13 | 0.08930 (15) | 0.17577 (13) | 0.81652 (11) | 0.0237 (4) | |
C14 | 0.04616 (16) | 0.25577 (13) | 0.81826 (12) | 0.0246 (4) | |
H11 | 0.0876 | 0.3044 | 0.8264 | 0.030* | |
C15 | −0.05751 (15) | 0.26864 (13) | 0.80849 (12) | 0.0248 (4) | |
C16 | −0.09980 (16) | 0.35216 (14) | 0.81064 (13) | 0.0288 (4) | |
H12 | −0.0583 | 0.4006 | 0.8196 | 0.035* | |
C17 | −0.20023 (17) | 0.36328 (14) | 0.79980 (13) | 0.0307 (5) | |
H13 | −0.2283 | 0.4192 | 0.8022 | 0.037* | |
C18 | −0.26222 (17) | 0.29157 (14) | 0.78510 (14) | 0.0307 (5) | |
H14 | −0.3317 | 0.2999 | 0.7771 | 0.037* | |
C19 | −0.22325 (16) | 0.21018 (14) | 0.78219 (13) | 0.0285 (4) | |
H15 | −0.2658 | 0.1629 | 0.7714 | 0.034* | |
C20 | −0.11913 (15) | 0.19570 (13) | 0.79522 (12) | 0.0243 (4) | |
C21 | 0.36725 (15) | 0.12905 (13) | 0.78190 (11) | 0.0232 (4) | |
C22 | 0.26459 (15) | 0.13343 (13) | 0.77035 (12) | 0.0238 (4) | |
C23 | 0.20017 (15) | 0.17027 (13) | 0.82767 (12) | 0.0241 (4) | |
C24 | 0.24162 (16) | 0.20631 (14) | 0.89221 (12) | 0.0259 (4) | |
H16 | 0.1990 | 0.2322 | 0.9295 | 0.031* | |
C25 | 0.34618 (16) | 0.20657 (13) | 0.90573 (12) | 0.0251 (4) | |
C26 | 0.38821 (17) | 0.24565 (15) | 0.97228 (13) | 0.0302 (5) | |
H17 | 0.3458 | 0.2714 | 1.0098 | 0.036* | |
C27 | 0.48981 (18) | 0.24670 (17) | 0.98319 (13) | 0.0339 (5) | |
H18 | 0.5175 | 0.2747 | 1.0272 | 0.041* | |
C28 | 0.55301 (17) | 0.20600 (16) | 0.92873 (13) | 0.0325 (5) | |
H19 | 0.6232 | 0.2068 | 0.9365 | 0.039* | |
C29 | 0.51451 (16) | 0.16557 (15) | 0.86516 (13) | 0.0282 (4) | |
H20 | 0.5581 | 0.1367 | 0.8303 | 0.034* | |
C30 | 0.40980 (15) | 0.16597 (13) | 0.85027 (12) | 0.0247 (4) | |
C31 | 0.43284 (15) | 0.08421 (13) | 0.72419 (12) | 0.0247 (4) | |
C32 | 0.43858 (15) | −0.00399 (13) | 0.72525 (12) | 0.0256 (4) | |
C33 | 0.49733 (16) | −0.04926 (15) | 0.67012 (13) | 0.0292 (4) | |
H21 | 0.4966 | −0.1103 | 0.6695 | 0.035* | |
C34 | 0.55447 (16) | −0.00578 (14) | 0.61831 (13) | 0.0296 (4) | |
H26 | 0.5929 | −0.0368 | 0.5814 | 0.035* | |
C35 | 0.55761 (15) | 0.08544 (14) | 0.61846 (12) | 0.0265 (4) | |
C36 | 0.62326 (17) | 0.13222 (15) | 0.56965 (13) | 0.0311 (5) | |
H25 | 0.6656 | 0.1020 | 0.5349 | 0.037* | |
C37 | 0.62687 (18) | 0.21972 (16) | 0.57159 (14) | 0.0329 (5) | |
H24 | 0.6714 | 0.2499 | 0.5385 | 0.039* | |
C38 | 0.56409 (17) | 0.26531 (15) | 0.62299 (13) | 0.0304 (5) | |
H23 | 0.5666 | 0.3263 | 0.6244 | 0.036* | |
C39 | 0.49921 (16) | 0.22195 (14) | 0.67112 (13) | 0.0278 (4) | |
H22 | 0.4567 | 0.2536 | 0.7047 | 0.033* | |
C40 | 0.49469 (15) | 0.13120 (14) | 0.67148 (12) | 0.0243 (4) | |
C41 | 0.01214 (19) | 0.23431 (16) | 0.62296 (13) | 0.0324 (5) | |
C42 | −0.0909 (2) | 0.25034 (19) | 0.59392 (16) | 0.0453 (6) | |
H29 | −0.0879 | 0.2708 | 0.5402 | 0.068* | |
H28 | −0.1232 | 0.2939 | 0.6264 | 0.068* | |
H27 | −0.1294 | 0.1969 | 0.5961 | 0.068* | |
C43 | 0.0796 (2) | 0.30987 (18) | 0.63304 (15) | 0.0488 (7) | |
H30 | 0.1436 | 0.2907 | 0.6543 | 0.073* | |
H31 | 0.0488 | 0.3511 | 0.6687 | 0.073* | |
H32 | 0.0907 | 0.3374 | 0.5827 | 0.073* | |
C44 | 0.26209 (19) | −0.00377 (17) | 0.96072 (14) | 0.0348 (5) | |
C45 | 0.3650 (2) | −0.0076 (2) | 0.99450 (16) | 0.0448 (6) | |
H33 | 0.4139 | −0.0143 | 0.9526 | 0.067* | |
H34 | 0.3698 | −0.0567 | 1.0300 | 0.067* | |
H35 | 0.3788 | 0.0455 | 1.0230 | 0.067* | |
C46 | 0.1773 (2) | 0.0140 (3) | 1.01510 (18) | 0.0623 (9) | |
H36 | 0.1140 | 0.0096 | 0.9869 | 0.093* | |
H37 | 0.1843 | 0.0721 | 1.0364 | 0.093* | |
H38 | 0.1783 | −0.0279 | 1.0575 | 0.093* | |
H1 | −0.046 (2) | 0.064 (2) | 0.6598 (19) | 0.052 (9)* | |
H2 | 0.128 (3) | 0.019 (2) | 0.832 (2) | 0.071 (11)* | |
H3 | 0.164 (3) | 0.125 (2) | 0.691 (2) | 0.070 (11)* | |
H4 | 0.347 (3) | −0.024 (2) | 0.812 (2) | 0.065 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0339 (8) | 0.0367 (8) | 0.0280 (7) | −0.0014 (7) | 0.0000 (7) | −0.0038 (7) |
O2 | 0.0236 (7) | 0.0261 (7) | 0.0396 (9) | 0.0025 (6) | −0.0030 (7) | −0.0038 (6) |
O3 | 0.0239 (7) | 0.0385 (8) | 0.0246 (7) | 0.0019 (7) | −0.0026 (6) | −0.0086 (6) |
O4 | 0.0288 (8) | 0.0273 (7) | 0.0354 (8) | −0.0021 (6) | 0.0032 (7) | −0.0007 (7) |
O5 | 0.0294 (8) | 0.0415 (9) | 0.0278 (7) | −0.0004 (7) | 0.0005 (6) | −0.0013 (7) |
O6 | 0.0310 (8) | 0.0364 (8) | 0.0321 (8) | −0.0003 (7) | 0.0003 (7) | 0.0029 (7) |
C1 | 0.0201 (9) | 0.0258 (9) | 0.0275 (10) | 0.0022 (8) | −0.0023 (8) | −0.0003 (8) |
C2 | 0.0236 (9) | 0.0304 (10) | 0.0273 (10) | 0.0046 (8) | −0.0039 (8) | 0.0006 (8) |
C3 | 0.0292 (10) | 0.0319 (11) | 0.0338 (11) | 0.0035 (9) | −0.0080 (9) | −0.0048 (9) |
C4 | 0.0256 (10) | 0.0305 (11) | 0.0397 (12) | −0.0029 (9) | −0.0082 (9) | −0.0018 (9) |
C5 | 0.0205 (9) | 0.0298 (10) | 0.0352 (11) | 0.0011 (8) | −0.0042 (8) | 0.0002 (9) |
C6 | 0.0238 (10) | 0.0377 (12) | 0.0413 (12) | −0.0041 (9) | −0.0034 (10) | 0.0052 (10) |
C7 | 0.0260 (11) | 0.0435 (13) | 0.0378 (12) | 0.0032 (10) | 0.0032 (10) | 0.0117 (10) |
C8 | 0.0302 (11) | 0.0369 (12) | 0.0316 (11) | 0.0049 (10) | −0.0015 (9) | 0.0009 (9) |
C9 | 0.0265 (10) | 0.0279 (10) | 0.0306 (10) | 0.0012 (9) | −0.0018 (9) | 0.0002 (8) |
C10 | 0.0195 (9) | 0.0253 (9) | 0.0314 (10) | 0.0023 (8) | −0.0030 (8) | 0.0004 (8) |
C11 | 0.0223 (9) | 0.0285 (10) | 0.0222 (9) | 0.0016 (8) | −0.0014 (8) | −0.0018 (8) |
C12 | 0.0250 (10) | 0.0268 (10) | 0.0209 (9) | 0.0018 (8) | 0.0000 (8) | −0.0019 (8) |
C13 | 0.0203 (9) | 0.0305 (10) | 0.0201 (8) | 0.0003 (8) | −0.0005 (7) | −0.0030 (8) |
C14 | 0.0219 (9) | 0.0282 (10) | 0.0238 (9) | −0.0027 (8) | −0.0002 (8) | −0.0006 (8) |
C15 | 0.0211 (9) | 0.0292 (10) | 0.0242 (9) | −0.0004 (8) | −0.0004 (8) | 0.0019 (8) |
C16 | 0.0274 (10) | 0.0271 (10) | 0.0318 (10) | 0.0009 (9) | −0.0021 (9) | 0.0014 (8) |
C17 | 0.0291 (11) | 0.0282 (10) | 0.0348 (11) | 0.0036 (9) | −0.0028 (9) | 0.0025 (9) |
C18 | 0.0229 (10) | 0.0329 (11) | 0.0363 (11) | 0.0027 (9) | −0.0012 (9) | 0.0025 (9) |
C19 | 0.0207 (10) | 0.0293 (10) | 0.0354 (11) | 0.0004 (8) | −0.0023 (9) | 0.0015 (9) |
C20 | 0.0233 (10) | 0.0281 (10) | 0.0216 (9) | −0.0012 (8) | −0.0011 (8) | −0.0001 (8) |
C21 | 0.0213 (9) | 0.0252 (9) | 0.0232 (9) | 0.0004 (8) | −0.0002 (8) | −0.0001 (8) |
C22 | 0.0229 (9) | 0.0262 (9) | 0.0223 (9) | −0.0005 (8) | −0.0020 (8) | −0.0008 (8) |
C23 | 0.0201 (9) | 0.0259 (9) | 0.0265 (9) | 0.0012 (8) | 0.0009 (8) | 0.0006 (8) |
C24 | 0.0232 (10) | 0.0285 (10) | 0.0262 (10) | 0.0016 (8) | 0.0017 (8) | −0.0029 (8) |
C25 | 0.0232 (10) | 0.0270 (9) | 0.0251 (9) | −0.0011 (8) | −0.0014 (8) | −0.0027 (8) |
C26 | 0.0269 (11) | 0.0351 (11) | 0.0286 (10) | 0.0007 (9) | 0.0010 (9) | −0.0047 (9) |
C27 | 0.0298 (11) | 0.0428 (13) | 0.0293 (11) | −0.0044 (10) | −0.0058 (9) | −0.0056 (10) |
C28 | 0.0235 (10) | 0.0431 (12) | 0.0310 (11) | −0.0007 (10) | −0.0042 (9) | 0.0004 (10) |
C29 | 0.0220 (10) | 0.0341 (11) | 0.0284 (10) | 0.0029 (8) | −0.0005 (8) | −0.0015 (9) |
C30 | 0.0222 (9) | 0.0277 (10) | 0.0242 (9) | 0.0004 (8) | −0.0014 (8) | 0.0014 (8) |
C31 | 0.0195 (9) | 0.0280 (9) | 0.0265 (9) | 0.0023 (8) | −0.0028 (8) | −0.0042 (8) |
C32 | 0.0200 (9) | 0.0280 (10) | 0.0287 (10) | 0.0009 (8) | −0.0013 (8) | −0.0011 (8) |
C33 | 0.0250 (10) | 0.0276 (10) | 0.0352 (11) | 0.0052 (8) | −0.0015 (9) | −0.0034 (9) |
C34 | 0.0234 (10) | 0.0325 (11) | 0.0328 (10) | 0.0064 (9) | −0.0003 (9) | −0.0062 (9) |
C35 | 0.0210 (9) | 0.0324 (10) | 0.0261 (9) | 0.0039 (8) | −0.0013 (8) | −0.0042 (8) |
C36 | 0.0258 (10) | 0.0404 (12) | 0.0270 (10) | 0.0067 (10) | 0.0036 (9) | −0.0030 (9) |
C37 | 0.0272 (11) | 0.0396 (12) | 0.0319 (11) | −0.0005 (9) | 0.0050 (9) | 0.0029 (9) |
C38 | 0.0309 (11) | 0.0303 (10) | 0.0301 (10) | 0.0003 (9) | −0.0008 (9) | 0.0008 (9) |
C39 | 0.0243 (10) | 0.0293 (10) | 0.0299 (10) | 0.0029 (8) | 0.0011 (9) | −0.0035 (8) |
C40 | 0.0202 (9) | 0.0294 (10) | 0.0233 (9) | 0.0012 (8) | −0.0018 (8) | −0.0018 (8) |
C41 | 0.0367 (12) | 0.0372 (12) | 0.0233 (10) | −0.0021 (10) | 0.0024 (9) | −0.0005 (9) |
C42 | 0.0441 (15) | 0.0485 (15) | 0.0434 (14) | 0.0079 (13) | −0.0071 (12) | 0.0023 (12) |
C43 | 0.0653 (18) | 0.0490 (15) | 0.0321 (12) | −0.0216 (14) | 0.0033 (13) | 0.0012 (11) |
C44 | 0.0355 (12) | 0.0389 (12) | 0.0299 (11) | 0.0020 (10) | 0.0009 (9) | 0.0047 (10) |
C45 | 0.0420 (14) | 0.0542 (16) | 0.0380 (13) | 0.0034 (13) | −0.0100 (11) | 0.0024 (12) |
C46 | 0.0497 (17) | 0.095 (3) | 0.0419 (15) | 0.0112 (18) | 0.0136 (14) | 0.0027 (17) |
Geometric parameters (Å, º) top
O1—C2 | 1.367 (3) | C22—C23 | 1.432 (3) |
O1—H1 | 0.95 (3) | C23—C24 | 1.364 (3) |
O2—C12 | 1.370 (3) | C24—C25 | 1.421 (3) |
O2—H2 | 0.95 (4) | C24—H16 | 0.9500 |
O3—C22 | 1.367 (2) | C25—C26 | 1.415 (3) |
O3—H3 | 0.94 (4) | C25—C30 | 1.428 (3) |
O4—C32 | 1.363 (3) | C26—C27 | 1.375 (3) |
O4—H4 | 0.94 (4) | C26—H17 | 0.9500 |
O5—C41 | 1.238 (3) | C27—C28 | 1.414 (3) |
O6—C44 | 1.221 (3) | C27—H18 | 0.9500 |
C1—C2 | 1.382 (3) | C28—C29 | 1.365 (3) |
C1—C10 | 1.431 (3) | C28—H19 | 0.9500 |
C1—C11 | 1.492 (3) | C29—C30 | 1.427 (3) |
C2—C3 | 1.416 (3) | C29—H20 | 0.9500 |
C3—C4 | 1.363 (3) | C31—C32 | 1.376 (3) |
C3—H5 | 0.9500 | C31—C40 | 1.431 (3) |
C4—C5 | 1.421 (3) | C32—C33 | 1.421 (3) |
C4—H6 | 0.9500 | C33—C34 | 1.357 (3) |
C5—C6 | 1.416 (3) | C33—H21 | 0.9500 |
C5—C10 | 1.426 (3) | C34—C35 | 1.421 (3) |
C6—C7 | 1.370 (4) | C34—H26 | 0.9500 |
C6—H7 | 0.9500 | C35—C36 | 1.419 (3) |
C7—C8 | 1.406 (4) | C35—C40 | 1.433 (3) |
C7—H8 | 0.9500 | C36—C37 | 1.363 (3) |
C8—C9 | 1.374 (3) | C36—H25 | 0.9500 |
C8—H9 | 0.9500 | C37—C38 | 1.413 (3) |
C9—C10 | 1.421 (3) | C37—H24 | 0.9500 |
C9—H10 | 0.9500 | C38—C39 | 1.378 (3) |
C11—C12 | 1.388 (3) | C38—H23 | 0.9500 |
C11—C20 | 1.430 (3) | C39—C40 | 1.414 (3) |
C12—C13 | 1.428 (3) | C39—H22 | 0.9500 |
C13—C14 | 1.374 (3) | C41—C42 | 1.490 (4) |
C13—C23 | 1.501 (3) | C41—C43 | 1.494 (4) |
C14—C15 | 1.414 (3) | C42—H29 | 0.9800 |
C14—H11 | 0.9500 | C42—H28 | 0.9800 |
C15—C16 | 1.419 (3) | C42—H27 | 0.9800 |
C15—C20 | 1.423 (3) | C43—H30 | 0.9800 |
C16—C17 | 1.370 (3) | C43—H31 | 0.9800 |
C16—H12 | 0.9500 | C43—H32 | 0.9800 |
C17—C18 | 1.415 (3) | C44—C46 | 1.499 (4) |
C17—H13 | 0.9500 | C44—C45 | 1.499 (4) |
C18—C19 | 1.371 (3) | C45—H33 | 0.9800 |
C18—H14 | 0.9500 | C45—H34 | 0.9800 |
C19—C20 | 1.431 (3) | C45—H35 | 0.9800 |
C19—H15 | 0.9500 | C46—H36 | 0.9800 |
C21—C22 | 1.392 (3) | C46—H37 | 0.9800 |
C21—C30 | 1.430 (3) | C46—H38 | 0.9800 |
C21—C31 | 1.500 (3) | | |
| | | |
C2—O1—H1 | 114 (2) | C26—C25—C30 | 119.66 (19) |
C12—O2—H2 | 112 (2) | C24—C25—C30 | 118.55 (18) |
C22—O3—H3 | 111 (2) | C27—C26—C25 | 120.7 (2) |
C32—O4—H4 | 115 (2) | C27—C26—H17 | 119.7 |
C2—C1—C10 | 118.66 (19) | C25—C26—H17 | 119.7 |
C2—C1—C11 | 120.76 (19) | C26—C27—C28 | 119.8 (2) |
C10—C1—C11 | 120.31 (18) | C26—C27—H18 | 120.1 |
O1—C2—C1 | 123.77 (19) | C28—C27—H18 | 120.1 |
O1—C2—C3 | 115.36 (19) | C29—C28—C27 | 120.9 (2) |
C1—C2—C3 | 120.9 (2) | C29—C28—H19 | 119.6 |
C4—C3—C2 | 120.8 (2) | C27—C28—H19 | 119.6 |
C4—C3—H5 | 119.6 | C28—C29—C30 | 121.0 (2) |
C2—C3—H5 | 119.6 | C28—C29—H20 | 119.5 |
C3—C4—C5 | 120.9 (2) | C30—C29—H20 | 119.5 |
C3—C4—H6 | 119.6 | C29—C30—C25 | 117.95 (19) |
C5—C4—H6 | 119.6 | C29—C30—C21 | 122.61 (19) |
C6—C5—C4 | 122.0 (2) | C25—C30—C21 | 119.42 (18) |
C6—C5—C10 | 119.9 (2) | C32—C31—C40 | 119.11 (19) |
C4—C5—C10 | 118.1 (2) | C32—C31—C21 | 119.25 (19) |
C7—C6—C5 | 121.0 (2) | C40—C31—C21 | 121.51 (18) |
C7—C6—H7 | 119.5 | O4—C32—C31 | 123.62 (19) |
C5—C6—H7 | 119.5 | O4—C32—C33 | 115.23 (19) |
C6—C7—C8 | 119.3 (2) | C31—C32—C33 | 121.1 (2) |
C6—C7—H8 | 120.3 | C34—C33—C32 | 120.3 (2) |
C8—C7—H8 | 120.3 | C34—C33—H21 | 119.8 |
C9—C8—C7 | 121.3 (2) | C32—C33—H21 | 119.8 |
C9—C8—H9 | 119.4 | C33—C34—C35 | 120.9 (2) |
C7—C8—H9 | 119.4 | C33—C34—H26 | 119.5 |
C8—C9—C10 | 120.9 (2) | C35—C34—H26 | 119.5 |
C8—C9—H10 | 119.6 | C36—C35—C34 | 122.0 (2) |
C10—C9—H10 | 119.6 | C36—C35—C40 | 119.2 (2) |
C9—C10—C5 | 117.6 (2) | C34—C35—C40 | 118.7 (2) |
C9—C10—C1 | 121.79 (19) | C37—C36—C35 | 121.4 (2) |
C5—C10—C1 | 120.55 (19) | C37—C36—H25 | 119.3 |
C12—C11—C20 | 119.82 (19) | C35—C36—H25 | 119.3 |
C12—C11—C1 | 121.83 (19) | C36—C37—C38 | 119.7 (2) |
C20—C11—C1 | 118.35 (17) | C36—C37—H24 | 120.1 |
O2—C12—C11 | 117.40 (19) | C38—C37—H24 | 120.1 |
O2—C12—C13 | 121.61 (18) | C39—C38—C37 | 120.5 (2) |
C11—C12—C13 | 120.99 (19) | C39—C38—H23 | 119.8 |
C14—C13—C12 | 118.50 (18) | C37—C38—H23 | 119.8 |
C14—C13—C23 | 117.76 (19) | C38—C39—C40 | 121.3 (2) |
C12—C13—C23 | 123.68 (19) | C38—C39—H22 | 119.4 |
C13—C14—C15 | 122.66 (19) | C40—C39—H22 | 119.4 |
C13—C14—H11 | 118.7 | C39—C40—C31 | 122.57 (19) |
C15—C14—H11 | 118.7 | C39—C40—C35 | 118.0 (2) |
C14—C15—C16 | 121.28 (19) | C31—C40—C35 | 119.44 (19) |
C14—C15—C20 | 118.46 (19) | O5—C41—C42 | 120.8 (2) |
C16—C15—C20 | 120.25 (19) | O5—C41—C43 | 121.2 (2) |
C17—C16—C15 | 120.3 (2) | C42—C41—C43 | 117.9 (2) |
C17—C16—H12 | 119.8 | C41—C42—H29 | 109.5 |
C15—C16—H12 | 119.8 | C41—C42—H28 | 109.5 |
C16—C17—C18 | 120.1 (2) | H29—C42—H28 | 109.5 |
C16—C17—H13 | 119.9 | C41—C42—H27 | 109.5 |
C18—C17—H13 | 119.9 | H29—C42—H27 | 109.5 |
C19—C18—C17 | 120.8 (2) | H28—C42—H27 | 109.5 |
C19—C18—H14 | 119.6 | C41—C43—H30 | 109.5 |
C17—C18—H14 | 119.6 | C41—C43—H31 | 109.5 |
C18—C19—C20 | 120.7 (2) | H30—C43—H31 | 109.5 |
C18—C19—H15 | 119.6 | C41—C43—H32 | 109.5 |
C20—C19—H15 | 119.6 | H30—C43—H32 | 109.5 |
C15—C20—C11 | 119.40 (18) | H31—C43—H32 | 109.5 |
C15—C20—C19 | 117.74 (19) | O6—C44—C46 | 121.1 (2) |
C11—C20—C19 | 122.85 (19) | O6—C44—C45 | 121.4 (2) |
C22—C21—C30 | 119.51 (18) | C46—C44—C45 | 117.5 (2) |
C22—C21—C31 | 120.49 (18) | C44—C45—H33 | 109.5 |
C30—C21—C31 | 119.99 (18) | C44—C45—H34 | 109.5 |
O3—C22—C21 | 117.80 (18) | H33—C45—H34 | 109.5 |
O3—C22—C23 | 121.07 (18) | C44—C45—H35 | 109.5 |
C21—C22—C23 | 121.13 (18) | H33—C45—H35 | 109.5 |
C24—C23—C22 | 118.80 (18) | H34—C45—H35 | 109.5 |
C24—C23—C13 | 118.97 (19) | C44—C46—H36 | 109.5 |
C22—C23—C13 | 122.11 (18) | C44—C46—H37 | 109.5 |
C23—C24—C25 | 122.46 (19) | H36—C46—H37 | 109.5 |
C23—C24—H16 | 118.8 | C44—C46—H38 | 109.5 |
C25—C24—H16 | 118.8 | H36—C46—H38 | 109.5 |
C26—C25—C24 | 121.8 (2) | H37—C46—H38 | 109.5 |
| | | |
C10—C1—C2—O1 | 178.28 (18) | C30—C21—C22—C23 | −3.3 (3) |
C11—C1—C2—O1 | 4.2 (3) | C31—C21—C22—C23 | 175.24 (18) |
C10—C1—C2—C3 | −0.9 (3) | O3—C22—C23—C24 | −176.10 (19) |
C11—C1—C2—C3 | −174.98 (19) | C21—C22—C23—C24 | 4.2 (3) |
O1—C2—C3—C4 | −178.8 (2) | O3—C22—C23—C13 | −0.3 (3) |
C1—C2—C3—C4 | 0.5 (3) | C21—C22—C23—C13 | 180.0 (2) |
C2—C3—C4—C5 | 0.8 (3) | C14—C13—C23—C24 | 54.9 (3) |
C3—C4—C5—C6 | 177.6 (2) | C12—C13—C23—C24 | −122.1 (2) |
C3—C4—C5—C10 | −1.6 (3) | C14—C13—C23—C22 | −120.9 (2) |
C4—C5—C6—C7 | −178.4 (2) | C12—C13—C23—C22 | 62.1 (3) |
C10—C5—C6—C7 | 0.8 (3) | C22—C23—C24—C25 | −1.8 (3) |
C5—C6—C7—C8 | −1.1 (3) | C13—C23—C24—C25 | −177.7 (2) |
C6—C7—C8—C9 | 0.0 (3) | C23—C24—C25—C26 | 178.8 (2) |
C7—C8—C9—C10 | 1.5 (3) | C23—C24—C25—C30 | −1.3 (3) |
C8—C9—C10—C5 | −1.8 (3) | C24—C25—C26—C27 | −178.5 (2) |
C8—C9—C10—C1 | 176.9 (2) | C30—C25—C26—C27 | 1.5 (3) |
C6—C5—C10—C9 | 0.7 (3) | C25—C26—C27—C28 | −2.0 (4) |
C4—C5—C10—C9 | 179.86 (19) | C26—C27—C28—C29 | 0.1 (4) |
C6—C5—C10—C1 | −178.02 (19) | C27—C28—C29—C30 | 2.4 (4) |
C4—C5—C10—C1 | 1.2 (3) | C28—C29—C30—C25 | −2.8 (3) |
C2—C1—C10—C9 | −178.58 (19) | C28—C29—C30—C21 | 176.0 (2) |
C11—C1—C10—C9 | −4.5 (3) | C26—C25—C30—C29 | 0.8 (3) |
C2—C1—C10—C5 | 0.0 (3) | C24—C25—C30—C29 | −179.1 (2) |
C11—C1—C10—C5 | 174.15 (19) | C26—C25—C30—C21 | −178.0 (2) |
C2—C1—C11—C12 | −78.6 (3) | C24—C25—C30—C21 | 2.1 (3) |
C10—C1—C11—C12 | 107.4 (2) | C22—C21—C30—C29 | −178.6 (2) |
C2—C1—C11—C20 | 102.1 (2) | C31—C21—C30—C29 | 2.8 (3) |
C10—C1—C11—C20 | −71.8 (3) | C22—C21—C30—C25 | 0.2 (3) |
C20—C11—C12—O2 | 177.95 (18) | C31—C21—C30—C25 | −178.41 (19) |
C1—C11—C12—O2 | −1.3 (3) | C22—C21—C31—C32 | −79.1 (3) |
C20—C11—C12—C13 | −2.6 (3) | C30—C21—C31—C32 | 99.4 (2) |
C1—C11—C12—C13 | 178.17 (18) | C22—C21—C31—C40 | 105.1 (2) |
O2—C12—C13—C14 | −176.00 (19) | C30—C21—C31—C40 | −76.3 (3) |
C11—C12—C13—C14 | 4.5 (3) | C40—C31—C32—O4 | 173.31 (18) |
O2—C12—C13—C23 | 1.0 (3) | C21—C31—C32—O4 | −2.5 (3) |
C11—C12—C13—C23 | −178.4 (2) | C40—C31—C32—C33 | −6.1 (3) |
C12—C13—C14—C15 | −2.8 (3) | C21—C31—C32—C33 | 178.02 (19) |
C23—C13—C14—C15 | −179.95 (19) | O4—C32—C33—C34 | −175.1 (2) |
C13—C14—C15—C16 | 179.96 (19) | C31—C32—C33—C34 | 4.4 (3) |
C13—C14—C15—C20 | −0.9 (3) | C32—C33—C34—C35 | 0.6 (3) |
C14—C15—C16—C17 | 179.0 (2) | C33—C34—C35—C36 | 174.3 (2) |
C20—C15—C16—C17 | −0.1 (3) | C33—C34—C35—C40 | −3.6 (3) |
C15—C16—C17—C18 | −1.1 (3) | C34—C35—C36—C37 | −178.6 (2) |
C16—C17—C18—C19 | 0.6 (4) | C40—C35—C36—C37 | −0.7 (3) |
C17—C18—C19—C20 | 1.0 (4) | C35—C36—C37—C38 | −0.1 (4) |
C14—C15—C20—C11 | 2.9 (3) | C36—C37—C38—C39 | 0.0 (4) |
C16—C15—C20—C11 | −178.0 (2) | C37—C38—C39—C40 | 1.1 (3) |
C14—C15—C20—C19 | −177.4 (2) | C38—C39—C40—C31 | 175.9 (2) |
C16—C15—C20—C19 | 1.7 (3) | C38—C39—C40—C35 | −1.9 (3) |
C12—C11—C20—C15 | −1.2 (3) | C32—C31—C40—C39 | −174.8 (2) |
C1—C11—C20—C15 | 178.08 (19) | C21—C31—C40—C39 | 1.0 (3) |
C12—C11—C20—C19 | 179.2 (2) | C32—C31—C40—C35 | 3.0 (3) |
C1—C11—C20—C19 | −1.6 (3) | C21—C31—C40—C35 | 178.74 (18) |
C18—C19—C20—C15 | −2.1 (3) | C36—C35—C40—C39 | 1.7 (3) |
C18—C19—C20—C11 | 177.5 (2) | C34—C35—C40—C39 | 179.7 (2) |
C30—C21—C22—O3 | 176.92 (18) | C36—C35—C40—C31 | −176.16 (19) |
C31—C21—C22—O3 | −4.5 (3) | C34—C35—C40—C31 | 1.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5 | 0.95 (3) | 1.94 (3) | 2.854 (2) | 160 (3) |
O2—H2···O6 | 0.95 (4) | 1.96 (4) | 2.885 (2) | 164 (3) |
O3—H3···O5 | 0.94 (4) | 1.98 (4) | 2.889 (2) | 163 (3) |
O4—H4···O6 | 0.94 (4) | 1.92 (4) | 2.803 (2) | 156 (3) |