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The structure of bharangin triacetate [systematic name: 6,10-bis(acetyloxy)-8-isopropyl-4,4,11
a-trimethyl-2-oxo-2,3,4,6,11,11
a-hexahydrobenzo[5,6]cyclohepta[1,2-
b]pyran-9-yl acetate], C
26H
32O
8, a tricyclic diterpenoid, contains a seven-membered cycloheptadiene ring forming two planar parts, a six-membered δ-lactone ring in a boat conformation and a planar benzene ring. The structure is stabilized by intra- and intermolecular C—H
O interactions.
Supporting information
CCDC reference: 263716
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.053
- wR factor = 0.128
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 25.00
From the CIF: _reflns_number_total 2528
Count of symmetry unique reflns 2528
Completeness (_total/calc) 100.00%
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
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
6,10-bis(acetyloxy)-8-isopropyl-4,4,11
a-trimethyl-2-oxo-2,3,4,6,11,11
a- hexahydrobenzo[5,6]cyclohepta[1,2-
b]pyran-9-yl acetate
top
Crystal data top
C26H32O8 | F(000) = 1008 |
Mr = 472.52 | Dx = 1.244 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5917 reflections |
a = 10.4278 (5) Å | θ = 2.3–24.8° |
b = 13.3828 (6) Å | µ = 0.09 mm−1 |
c = 18.0857 (9) Å | T = 273 K |
V = 2523.9 (2) Å3 | Transparent needles, colorless |
Z = 4 | 0.20 × 0.15 × 0.10 mm |
Data collection top
CCD Area Detector diffractometer | 2435 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −12→12 |
18391 measured reflections | k = −15→15 |
2528 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.25 | w = 1/[σ2(Fo2) + (0.0582P)2 + 0.6697P] where P = (Fo2 + 2Fc2)/3 |
2528 reflections | (Δ/σ)max < 0.001 |
315 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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 | |
C1 | 0.2154 (3) | 0.7694 (2) | 1.02533 (17) | 0.0388 (7) | |
H1 | 0.1477 | 0.7285 | 1.0476 | 0.047* | |
C2 | 0.1713 (3) | 0.8759 (3) | 1.02743 (18) | 0.0425 (8) | |
H2 | 0.1102 | 0.8886 | 1.0637 | 0.051* | |
C3 | 0.2021 (3) | 0.9552 (2) | 0.98784 (19) | 0.0412 (8) | |
C4 | 0.2989 (3) | 0.9591 (2) | 0.92547 (19) | 0.0419 (8) | |
C5 | 0.3924 (3) | 0.8715 (2) | 0.92494 (18) | 0.0382 (7) | |
H5A | 0.4615 | 0.8861 | 0.8907 | 0.046* | |
H5B | 0.4295 | 0.8645 | 0.9738 | 0.046* | |
C6 | 0.3307 (3) | 0.7739 (2) | 0.90315 (18) | 0.0371 (7) | |
C7 | 0.2462 (3) | 0.7250 (2) | 0.95092 (17) | 0.0363 (7) | |
C8 | 0.1881 (3) | 0.6365 (2) | 0.92993 (17) | 0.0377 (7) | |
H8 | 0.1357 | 0.6039 | 0.9638 | 0.045* | |
C9 | 0.2048 (3) | 0.5940 (2) | 0.86040 (18) | 0.0402 (8) | |
C10 | 0.2869 (3) | 0.6442 (2) | 0.81278 (18) | 0.0403 (8) | |
C11 | 0.3499 (3) | 0.7308 (2) | 0.83437 (18) | 0.0398 (7) | |
C12 | 0.1393 (4) | 1.0564 (3) | 1.0091 (2) | 0.0577 (10) | |
C13 | 0.1953 (4) | 1.1416 (3) | 0.9624 (3) | 0.0665 (12) | |
H13A | 0.1566 | 1.1401 | 0.9137 | 0.080* | |
H13B | 0.1733 | 1.2050 | 0.9852 | 0.080* | |
C14 | 0.3375 (5) | 1.1351 (3) | 0.9546 (2) | 0.0607 (11) | |
C15 | −0.0067 (4) | 1.0507 (4) | 0.9961 (4) | 0.101 (2) | |
H15A | −0.0446 | 1.1146 | 1.0063 | 0.151* | |
H15B | −0.0433 | 1.0013 | 1.0283 | 0.151* | |
H15C | −0.0231 | 1.0327 | 0.9456 | 0.151* | |
C16 | 0.1687 (6) | 1.0799 (3) | 1.0902 (3) | 0.0837 (16) | |
H16A | 0.2598 | 1.0852 | 1.0968 | 0.126* | |
H16B | 0.1360 | 1.0272 | 1.1209 | 0.126* | |
H16C | 0.1288 | 1.1419 | 1.1036 | 0.126* | |
C17 | 0.2408 (4) | 0.9714 (3) | 0.8481 (2) | 0.0577 (10) | |
H17A | 0.1743 | 1.0210 | 0.8496 | 0.087* | |
H17B | 0.2053 | 0.9088 | 0.8321 | 0.087* | |
H17C | 0.3064 | 0.9921 | 0.8141 | 0.087* | |
C18 | 0.3309 (4) | 0.6883 (2) | 1.1220 (2) | 0.0466 (8) | |
C19 | 0.4464 (5) | 0.6917 (4) | 1.1689 (3) | 0.0800 (15) | |
H19A | 0.4364 | 0.7427 | 1.2058 | 0.120* | |
H19B | 0.5199 | 0.7065 | 1.1389 | 0.120* | |
H19C | 0.4581 | 0.6282 | 1.1926 | 0.120* | |
C20 | 0.1325 (4) | 0.5003 (3) | 0.8378 (2) | 0.0491 (9) | |
H20 | 0.1748 | 0.4732 | 0.7938 | 0.059* | |
C21 | −0.0049 (4) | 0.5256 (4) | 0.8166 (3) | 0.0741 (13) | |
H21A | −0.0467 | 0.5579 | 0.8574 | 0.111* | |
H21B | −0.0501 | 0.4654 | 0.8043 | 0.111* | |
H21C | −0.0047 | 0.5696 | 0.7747 | 0.111* | |
C22 | 0.1357 (5) | 0.4198 (3) | 0.8971 (3) | 0.0711 (13) | |
H22A | 0.2230 | 0.4065 | 0.9107 | 0.107* | |
H22B | 0.0971 | 0.3598 | 0.8783 | 0.107* | |
H22C | 0.0890 | 0.4422 | 0.9397 | 0.107* | |
C23 | 0.2441 (4) | 0.6510 (3) | 0.6855 (2) | 0.0578 (10) | |
C24 | 0.2943 (5) | 0.6175 (4) | 0.6129 (2) | 0.0713 (13) | |
H24A | 0.2442 | 0.6468 | 0.5740 | 0.107* | |
H24B | 0.2890 | 0.5460 | 0.6098 | 0.107* | |
H24C | 0.3821 | 0.6379 | 0.6080 | 0.107* | |
C25 | 0.5453 (4) | 0.7431 (4) | 0.7696 (2) | 0.0561 (10) | |
C26 | 0.6121 (5) | 0.8042 (5) | 0.7136 (2) | 0.0858 (16) | |
H26A | 0.6991 | 0.7817 | 0.7089 | 0.129* | |
H26B | 0.6113 | 0.8730 | 0.7286 | 0.129* | |
H26C | 0.5692 | 0.7976 | 0.6669 | 0.129* | |
O1 | 0.3854 (3) | 1.04403 (17) | 0.93973 (14) | 0.0522 (6) | |
O2 | 0.4099 (4) | 1.2031 (2) | 0.9621 (2) | 0.0865 (11) | |
O3 | 0.3282 (2) | 0.76278 (16) | 1.07346 (12) | 0.0427 (6) | |
O4 | 0.2491 (4) | 0.6263 (2) | 1.1271 (2) | 0.0881 (11) | |
O5 | 0.3112 (2) | 0.60797 (18) | 0.74178 (12) | 0.0496 (6) | |
O6 | 0.1604 (4) | 0.7089 (3) | 0.69661 (18) | 0.0997 (13) | |
O7 | 0.4256 (2) | 0.78043 (18) | 0.78200 (13) | 0.0483 (6) | |
O8 | 0.5862 (3) | 0.6718 (3) | 0.80110 (18) | 0.0849 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0388 (16) | 0.0385 (17) | 0.0391 (17) | −0.0052 (15) | 0.0013 (14) | 0.0006 (14) |
C2 | 0.0409 (17) | 0.0439 (18) | 0.0426 (18) | 0.0022 (16) | 0.0067 (15) | −0.0085 (15) |
C3 | 0.0361 (17) | 0.0399 (17) | 0.0477 (18) | −0.0011 (15) | −0.0036 (15) | −0.0046 (15) |
C4 | 0.0425 (18) | 0.0360 (16) | 0.0472 (18) | −0.0057 (15) | −0.0058 (16) | 0.0012 (15) |
C5 | 0.0341 (16) | 0.0418 (17) | 0.0387 (17) | −0.0034 (14) | 0.0046 (14) | 0.0002 (14) |
C6 | 0.0347 (15) | 0.0346 (15) | 0.0421 (17) | 0.0051 (14) | −0.0014 (14) | −0.0006 (14) |
C7 | 0.0328 (15) | 0.0364 (16) | 0.0397 (17) | 0.0044 (14) | 0.0042 (14) | 0.0019 (14) |
C8 | 0.0378 (16) | 0.0351 (16) | 0.0401 (17) | −0.0024 (14) | 0.0062 (14) | 0.0023 (14) |
C9 | 0.0407 (17) | 0.0350 (16) | 0.0448 (18) | 0.0039 (15) | 0.0024 (15) | −0.0032 (14) |
C10 | 0.0424 (18) | 0.0410 (17) | 0.0375 (17) | 0.0037 (15) | 0.0048 (15) | −0.0015 (14) |
C11 | 0.0385 (17) | 0.0395 (17) | 0.0416 (17) | −0.0013 (15) | 0.0046 (14) | 0.0023 (15) |
C12 | 0.052 (2) | 0.0382 (18) | 0.083 (3) | 0.0122 (17) | −0.002 (2) | −0.0071 (19) |
C13 | 0.076 (3) | 0.0367 (19) | 0.086 (3) | 0.010 (2) | −0.016 (3) | −0.004 (2) |
C14 | 0.081 (3) | 0.0342 (19) | 0.067 (3) | −0.007 (2) | 0.001 (2) | −0.0003 (18) |
C15 | 0.051 (3) | 0.056 (3) | 0.195 (6) | 0.020 (2) | 0.001 (3) | −0.018 (4) |
C16 | 0.122 (4) | 0.050 (2) | 0.079 (3) | 0.009 (3) | 0.026 (3) | −0.016 (2) |
C17 | 0.069 (3) | 0.050 (2) | 0.054 (2) | 0.001 (2) | −0.008 (2) | 0.0078 (17) |
C18 | 0.051 (2) | 0.0374 (18) | 0.051 (2) | 0.0024 (16) | 0.0070 (17) | 0.0063 (16) |
C19 | 0.072 (3) | 0.085 (3) | 0.083 (3) | −0.004 (3) | −0.009 (3) | 0.041 (3) |
C20 | 0.057 (2) | 0.0401 (18) | 0.050 (2) | −0.0033 (17) | 0.0111 (18) | −0.0113 (16) |
C21 | 0.058 (3) | 0.073 (3) | 0.091 (3) | −0.015 (2) | −0.002 (2) | −0.028 (3) |
C22 | 0.095 (3) | 0.046 (2) | 0.072 (3) | −0.014 (2) | 0.009 (3) | −0.005 (2) |
C23 | 0.052 (2) | 0.076 (3) | 0.045 (2) | −0.011 (2) | 0.0014 (19) | 0.003 (2) |
C24 | 0.091 (3) | 0.081 (3) | 0.041 (2) | −0.032 (3) | 0.006 (2) | −0.004 (2) |
C25 | 0.041 (2) | 0.090 (3) | 0.0369 (19) | −0.008 (2) | 0.0010 (15) | 0.000 (2) |
C26 | 0.056 (2) | 0.146 (5) | 0.055 (2) | −0.024 (3) | 0.010 (2) | 0.017 (3) |
O1 | 0.0560 (15) | 0.0345 (12) | 0.0660 (16) | −0.0103 (12) | 0.0003 (13) | −0.0070 (12) |
O2 | 0.098 (2) | 0.0422 (15) | 0.119 (3) | −0.0268 (17) | 0.013 (2) | −0.0111 (17) |
O3 | 0.0479 (13) | 0.0391 (12) | 0.0411 (12) | −0.0061 (11) | −0.0028 (11) | 0.0054 (10) |
O4 | 0.094 (2) | 0.0604 (19) | 0.110 (3) | −0.025 (2) | −0.015 (2) | 0.0361 (19) |
O5 | 0.0586 (15) | 0.0504 (14) | 0.0398 (12) | −0.0023 (13) | 0.0090 (12) | −0.0068 (11) |
O6 | 0.088 (2) | 0.147 (3) | 0.064 (2) | 0.045 (3) | −0.0018 (19) | 0.010 (2) |
O7 | 0.0503 (14) | 0.0501 (13) | 0.0445 (13) | −0.0049 (12) | 0.0139 (11) | 0.0019 (11) |
O8 | 0.0549 (18) | 0.126 (3) | 0.074 (2) | 0.0165 (19) | 0.0066 (16) | 0.028 (2) |
Geometric parameters (Å, º) top
C1—O3 | 1.466 (4) | C15—H15C | 0.9600 |
C1—C2 | 1.498 (5) | C16—H16A | 0.9600 |
C1—C7 | 1.506 (4) | C16—H16B | 0.9600 |
C1—H1 | 0.9800 | C16—H16C | 0.9600 |
C2—C3 | 1.320 (5) | C17—H17A | 0.9600 |
C2—H2 | 0.9300 | C17—H17B | 0.9600 |
C3—C4 | 1.514 (5) | C17—H17C | 0.9600 |
C3—C12 | 1.553 (5) | C18—O4 | 1.193 (5) |
C4—O1 | 1.474 (4) | C18—O3 | 1.328 (4) |
C4—C5 | 1.524 (5) | C18—C19 | 1.474 (6) |
C4—C17 | 1.534 (5) | C19—H19A | 0.9600 |
C5—C6 | 1.509 (5) | C19—H19B | 0.9600 |
C5—H5A | 0.9700 | C19—H19C | 0.9600 |
C5—H5B | 0.9700 | C20—C22 | 1.521 (6) |
C6—C11 | 1.386 (4) | C20—C21 | 1.522 (6) |
C6—C7 | 1.397 (4) | C20—H20 | 0.9800 |
C7—C8 | 1.383 (5) | C21—H21A | 0.9600 |
C8—C9 | 1.391 (5) | C21—H21B | 0.9600 |
C8—H8 | 0.9300 | C21—H21C | 0.9600 |
C9—C10 | 1.388 (5) | C22—H22A | 0.9600 |
C9—C20 | 1.520 (5) | C22—H22B | 0.9600 |
C10—C11 | 1.388 (5) | C22—H22C | 0.9600 |
C10—O5 | 1.396 (4) | C23—O6 | 1.185 (5) |
C11—O7 | 1.401 (4) | C23—O5 | 1.363 (5) |
C12—C16 | 1.531 (7) | C23—C24 | 1.482 (6) |
C12—C13 | 1.535 (6) | C24—H24A | 0.9600 |
C12—C15 | 1.542 (6) | C24—H24B | 0.9600 |
C13—C14 | 1.492 (7) | C24—H24C | 0.9600 |
C13—H13A | 0.9700 | C25—O8 | 1.190 (5) |
C13—H13B | 0.9700 | C25—O7 | 1.363 (5) |
C14—O2 | 1.190 (5) | C25—C26 | 1.477 (6) |
C14—O1 | 1.344 (5) | C26—H26A | 0.9600 |
C15—H15A | 0.9600 | C26—H26B | 0.9600 |
C15—H15B | 0.9600 | C26—H26C | 0.9600 |
| | | |
O3—C1—C2 | 106.8 (3) | H15B—C15—H15C | 109.5 |
O3—C1—C7 | 109.6 (2) | C12—C16—H16A | 109.5 |
C2—C1—C7 | 117.6 (3) | C12—C16—H16B | 109.5 |
O3—C1—H1 | 107.5 | H16A—C16—H16B | 109.5 |
C2—C1—H1 | 107.5 | C12—C16—H16C | 109.5 |
C7—C1—H1 | 107.5 | H16A—C16—H16C | 109.5 |
C3—C2—C1 | 132.5 (3) | H16B—C16—H16C | 109.5 |
C3—C2—H2 | 113.7 | C4—C17—H17A | 109.5 |
C1—C2—H2 | 113.7 | C4—C17—H17B | 109.5 |
C2—C3—C4 | 126.5 (3) | H17A—C17—H17B | 109.5 |
C2—C3—C12 | 117.6 (3) | C4—C17—H17C | 109.5 |
C4—C3—C12 | 115.8 (3) | H17A—C17—H17C | 109.5 |
O1—C4—C3 | 107.7 (3) | H17B—C17—H17C | 109.5 |
O1—C4—C5 | 101.7 (3) | O4—C18—O3 | 123.9 (4) |
C3—C4—C5 | 113.8 (3) | O4—C18—C19 | 124.2 (3) |
O1—C4—C17 | 108.6 (3) | O3—C18—C19 | 112.0 (3) |
C3—C4—C17 | 114.8 (3) | C18—C19—H19A | 109.5 |
C5—C4—C17 | 109.2 (3) | C18—C19—H19B | 109.5 |
C6—C5—C4 | 113.3 (3) | H19A—C19—H19B | 109.5 |
C6—C5—H5A | 108.9 | C18—C19—H19C | 109.5 |
C4—C5—H5A | 108.9 | H19A—C19—H19C | 109.5 |
C6—C5—H5B | 108.9 | H19B—C19—H19C | 109.5 |
C4—C5—H5B | 108.9 | C9—C20—C22 | 112.6 (3) |
H5A—C5—H5B | 107.7 | C9—C20—C21 | 110.5 (3) |
C11—C6—C7 | 116.8 (3) | C22—C20—C21 | 110.9 (4) |
C11—C6—C5 | 122.3 (3) | C9—C20—H20 | 107.5 |
C7—C6—C5 | 120.8 (3) | C22—C20—H20 | 107.5 |
C8—C7—C6 | 120.5 (3) | C21—C20—H20 | 107.5 |
C8—C7—C1 | 119.4 (3) | C20—C21—H21A | 109.5 |
C6—C7—C1 | 120.2 (3) | C20—C21—H21B | 109.5 |
C7—C8—C9 | 122.9 (3) | H21A—C21—H21B | 109.5 |
C7—C8—H8 | 118.5 | C20—C21—H21C | 109.5 |
C9—C8—H8 | 118.5 | H21A—C21—H21C | 109.5 |
C10—C9—C8 | 116.1 (3) | H21B—C21—H21C | 109.5 |
C10—C9—C20 | 122.6 (3) | C20—C22—H22A | 109.5 |
C8—C9—C20 | 121.2 (3) | C20—C22—H22B | 109.5 |
C11—C10—C9 | 121.4 (3) | H22A—C22—H22B | 109.5 |
C11—C10—O5 | 117.6 (3) | C20—C22—H22C | 109.5 |
C9—C10—O5 | 121.0 (3) | H22A—C22—H22C | 109.5 |
C6—C11—C10 | 122.1 (3) | H22B—C22—H22C | 109.5 |
C6—C11—O7 | 119.4 (3) | O6—C23—O5 | 121.9 (4) |
C10—C11—O7 | 118.2 (3) | O6—C23—C24 | 127.5 (4) |
C16—C12—C13 | 107.3 (4) | O5—C23—C24 | 110.6 (4) |
C16—C12—C15 | 110.7 (5) | C23—C24—H24A | 109.5 |
C13—C12—C15 | 109.1 (4) | C23—C24—H24B | 109.5 |
C16—C12—C3 | 109.4 (3) | H24A—C24—H24B | 109.5 |
C13—C12—C3 | 110.6 (3) | C23—C24—H24C | 109.5 |
C15—C12—C3 | 109.6 (3) | H24A—C24—H24C | 109.5 |
C14—C13—C12 | 112.8 (3) | H24B—C24—H24C | 109.5 |
C14—C13—H13A | 109.0 | O8—C25—O7 | 122.9 (4) |
C12—C13—H13A | 109.0 | O8—C25—C26 | 127.1 (4) |
C14—C13—H13B | 109.0 | O7—C25—C26 | 110.0 (4) |
C12—C13—H13B | 109.0 | C25—C26—H26A | 109.5 |
H13A—C13—H13B | 107.8 | C25—C26—H26B | 109.5 |
O2—C14—O1 | 118.7 (4) | H26A—C26—H26B | 109.5 |
O2—C14—C13 | 125.1 (4) | C25—C26—H26C | 109.5 |
O1—C14—C13 | 116.2 (3) | H26A—C26—H26C | 109.5 |
C12—C15—H15A | 109.5 | H26B—C26—H26C | 109.5 |
C12—C15—H15B | 109.5 | C14—O1—C4 | 120.5 (3) |
H15A—C15—H15B | 109.5 | C18—O3—C1 | 117.0 (3) |
C12—C15—H15C | 109.5 | C23—O5—C10 | 116.6 (3) |
H15A—C15—H15C | 109.5 | C25—O7—C11 | 117.0 (3) |
| | | |
O3—C1—C2—C3 | 88.4 (4) | O5—C10—C11—C6 | 178.8 (3) |
C7—C1—C2—C3 | −35.3 (5) | C9—C10—C11—O7 | −176.5 (3) |
C1—C2—C3—C4 | −0.6 (6) | O5—C10—C11—O7 | 4.9 (4) |
C1—C2—C3—C12 | −177.2 (4) | C2—C3—C12—C16 | 56.6 (5) |
C2—C3—C4—O1 | −130.1 (4) | C4—C3—C12—C16 | −120.3 (4) |
C12—C3—C4—O1 | 46.5 (4) | C2—C3—C12—C13 | 174.6 (3) |
C2—C3—C4—C5 | −18.1 (5) | C4—C3—C12—C13 | −2.3 (5) |
C12—C3—C4—C5 | 158.5 (3) | C2—C3—C12—C15 | −65.0 (5) |
C2—C3—C4—C17 | 108.8 (4) | C4—C3—C12—C15 | 118.1 (4) |
C12—C3—C4—C17 | −74.6 (4) | C16—C12—C13—C14 | 76.1 (5) |
O1—C4—C5—C6 | −173.9 (3) | C15—C12—C13—C14 | −163.9 (4) |
C3—C4—C5—C6 | 70.6 (4) | C3—C12—C13—C14 | −43.2 (5) |
C17—C4—C5—C6 | −59.2 (4) | C12—C13—C14—O2 | −134.1 (5) |
C4—C5—C6—C11 | 105.5 (4) | C12—C13—C14—O1 | 44.2 (6) |
C4—C5—C6—C7 | −71.5 (4) | C10—C9—C20—C22 | 136.0 (4) |
C11—C6—C7—C8 | 1.6 (4) | C8—C9—C20—C22 | −46.3 (5) |
C5—C6—C7—C8 | 178.7 (3) | C10—C9—C20—C21 | −99.3 (4) |
C11—C6—C7—C1 | −177.2 (3) | C8—C9—C20—C21 | 78.3 (4) |
C5—C6—C7—C1 | −0.1 (4) | O2—C14—O1—C4 | −176.2 (4) |
O3—C1—C7—C8 | 111.2 (3) | C13—C14—O1—C4 | 5.4 (6) |
C2—C1—C7—C8 | −126.6 (3) | C3—C4—O1—C14 | −50.8 (4) |
O3—C1—C7—C6 | −69.9 (4) | C5—C4—O1—C14 | −170.7 (3) |
C2—C1—C7—C6 | 52.3 (4) | C17—C4—O1—C14 | 74.2 (4) |
C6—C7—C8—C9 | −3.2 (5) | O4—C18—O3—C1 | 1.8 (5) |
C1—C7—C8—C9 | 175.6 (3) | C19—C18—O3—C1 | −177.9 (3) |
C7—C8—C9—C10 | 1.8 (5) | C2—C1—O3—C18 | 132.1 (3) |
C7—C8—C9—C20 | −176.0 (3) | C7—C1—O3—C18 | −99.4 (3) |
C8—C9—C10—C11 | 1.0 (5) | O6—C23—O5—C10 | −7.3 (6) |
C20—C9—C10—C11 | 178.8 (3) | C24—C23—O5—C10 | 170.7 (3) |
C8—C9—C10—O5 | 179.6 (3) | C11—C10—O5—C23 | −82.3 (4) |
C20—C9—C10—O5 | −2.6 (5) | C9—C10—O5—C23 | 99.0 (4) |
C7—C6—C11—C10 | 1.1 (5) | O8—C25—O7—C11 | 0.0 (5) |
C5—C6—C11—C10 | −175.9 (3) | C26—C25—O7—C11 | −179.7 (3) |
C7—C6—C11—O7 | 175.0 (3) | C6—C11—O7—C25 | 105.6 (4) |
C5—C6—C11—O7 | −2.1 (5) | C10—C11—O7—C25 | −80.3 (4) |
C9—C10—C11—C6 | −2.5 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O3 | 0.97 | 2.49 | 3.127 (4) | 123 |
C2—H2···O8i | 0.93 | 2.59 | 3.288 (5) | 133 |
C15—H15A···O2ii | 0.96 | 2.55 | 3.490 (6) | 166 |
C24—H24B···O4iii | 0.96 | 2.36 | 3.304 (6) | 167 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x−1/2, −y+5/2, −z+2; (iii) −x+1/2, −y+1, z−1/2. |
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