The title compound, (
E)-3-{2-[3-(2-bromophenyl)-6a,10
b-dimethyl-8-methyleneperhydronaphtho[2,1-
d][1,3]dioxin-7-yl]ethylidene}-4-hydroxy-4,5-dihydrofuran-2(3
H)-one, C
27H
33BrO
5, an andrographolide derivative, was semi-synthesized using andrographolide as a starting material. The structure contains three fused six-membered rings adopting chair conformations and a five-membered ring adopting an envelope conformation. The 2-bromophenyl group is twisted away from the attached ring. O—H
O hydrogen bonds in the structure form chains along the
b axis which are interlinked
via C—H
O interactions.
Supporting information
CCDC reference: 298398
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.109
- Data-to-parameter ratio = 36.3
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.417 0.732
Tmin(prime) and Tmax expected: 0.489 0.716
RR(prime) = 0.835
Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
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 36.23
From the CIF: _reflns_number_total 10919
Count of symmetry unique reflns 6396
Completeness (_total/calc) 170.72%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 4523
Fraction of Friedel pairs measured 0.707
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: H.K. Fun and I.A. Razak are supervisors
of Shea-Lin Ng whereas J. Stanslas is supervisor
of S. R. Sagineedu and S. R. Jada in this collaborative
pulication. UPM is involved in the extraction and synthesis
of the title compound and USM is involved in the structure
determination. All parties are involved in writing up the
manuscript.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
(
E)-3-{2-[3-(2-bromophenyl)-6a,10
b-dimethyl-8-
methyleneperhydronaphtho[2,1-
d][1,3]dioxin-7-yl]ethylidene}-4-hydroxy-
4,5-dihydrofuran-2(3
H)-one
top
Crystal data top
C27H33BrO5 | F(000) = 1080 |
Mr = 517.44 | Dx = 1.437 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5896 reflections |
a = 7.6735 (1) Å | θ = 1.5–36.2° |
b = 11.7744 (2) Å | µ = 1.76 mm−1 |
c = 26.4742 (5) Å | T = 297 K |
V = 2391.97 (7) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.26 × 0.19 mm |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 10919 independent reflections |
Radiation source: fine-focus sealed tube | 4609 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 8.33 pixels mm-1 | θmax = 36.2°, θmin = 1.5° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −15→19 |
Tmin = 0.417, Tmax = 0.732 | l = −43→24 |
36359 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0329P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.001 |
10919 reflections | Δρmax = 0.30 e Å−3 |
301 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 4719 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.011 (6) |
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 | x | y | z | Uiso*/Ueq | |
Br1 | −0.16374 (4) | 0.65047 (2) | 0.393923 (11) | 0.05707 (10) | |
O1 | 0.2204 (2) | 0.53554 (12) | 0.42700 (6) | 0.0430 (4) | |
O2 | 0.3664 (2) | 0.68401 (12) | 0.46748 (6) | 0.0428 (4) | |
O3 | −0.1087 (3) | −0.07353 (15) | 0.73084 (8) | 0.0655 (6) | |
O4 | 0.1794 (3) | −0.08101 (15) | 0.73310 (7) | 0.0668 (6) | |
O5 | −0.1790 (3) | 0.17515 (15) | 0.74915 (7) | 0.0601 (5) | |
H5A | −0.1418 | 0.2400 | 0.7457 | 0.090* | |
C1 | 0.0366 (3) | 0.7293 (2) | 0.36961 (9) | 0.0381 (5) | |
C2 | 0.0163 (4) | 0.7943 (2) | 0.32641 (9) | 0.0474 (7) | |
H2 | −0.0912 | 0.7994 | 0.3104 | 0.057* | |
C3 | 0.1598 (4) | 0.8512 (2) | 0.30780 (9) | 0.0510 (6) | |
H3 | 0.1488 | 0.8950 | 0.2787 | 0.061* | |
C4 | 0.3181 (4) | 0.8442 (2) | 0.33148 (9) | 0.0514 (6) | |
H4 | 0.4139 | 0.8827 | 0.3185 | 0.062* | |
C5 | 0.3349 (4) | 0.77991 (19) | 0.37466 (9) | 0.0436 (6) | |
H5 | 0.4427 | 0.7754 | 0.3906 | 0.052* | |
C6 | 0.1933 (3) | 0.72134 (17) | 0.39493 (9) | 0.0363 (5) | |
C7 | 0.2135 (3) | 0.65126 (19) | 0.44227 (8) | 0.0368 (5) | |
H7 | 0.1126 | 0.6632 | 0.4644 | 0.044* | |
C8 | 0.2423 (3) | 0.45869 (19) | 0.46912 (9) | 0.0397 (6) | |
H8 | 0.2686 | 0.3842 | 0.4545 | 0.048* | |
C9 | 0.0763 (3) | 0.4441 (2) | 0.49913 (10) | 0.0487 (7) | |
H9A | −0.0163 | 0.4182 | 0.4770 | 0.058* | |
H9B | 0.0417 | 0.5165 | 0.5134 | 0.058* | |
C10 | 0.1038 (3) | 0.3574 (2) | 0.54169 (9) | 0.0481 (6) | |
H10A | 0.1327 | 0.2845 | 0.5269 | 0.058* | |
H10B | −0.0046 | 0.3486 | 0.5601 | 0.058* | |
C11 | 0.2486 (3) | 0.39119 (18) | 0.57905 (8) | 0.0328 (5) | |
C12 | 0.2893 (3) | 0.28850 (18) | 0.61521 (8) | 0.0356 (5) | |
H12 | 0.3244 | 0.2251 | 0.5935 | 0.043* | |
C13 | 0.4461 (3) | 0.31655 (18) | 0.64788 (9) | 0.0378 (5) | |
C14 | 0.6075 (3) | 0.3479 (2) | 0.61915 (9) | 0.0476 (6) | |
H14A | 0.6505 | 0.2818 | 0.6012 | 0.057* | |
H14B | 0.6971 | 0.3721 | 0.6427 | 0.057* | |
C15 | 0.5713 (3) | 0.4433 (2) | 0.58142 (9) | 0.0442 (6) | |
H15A | 0.5461 | 0.5130 | 0.5996 | 0.053* | |
H15B | 0.6739 | 0.4561 | 0.5608 | 0.053* | |
C16 | 0.4171 (3) | 0.41317 (19) | 0.54751 (8) | 0.0329 (5) | |
H16 | 0.4471 | 0.3386 | 0.5335 | 0.040* | |
C17 | 0.4017 (3) | 0.49201 (18) | 0.50032 (8) | 0.0339 (5) | |
C18 | 0.3862 (3) | 0.61880 (18) | 0.51291 (9) | 0.0407 (6) | |
H18A | 0.2864 | 0.6311 | 0.5347 | 0.049* | |
H18B | 0.4898 | 0.6436 | 0.5308 | 0.049* | |
C19 | 0.1325 (3) | 0.2473 (2) | 0.64542 (10) | 0.0445 (6) | |
H19A | 0.1046 | 0.3041 | 0.6707 | 0.053* | |
H19B | 0.0334 | 0.2416 | 0.6228 | 0.053* | |
C20 | 0.1555 (4) | 0.13475 (19) | 0.67157 (8) | 0.0418 (5) | |
H20 | 0.2652 | 0.1012 | 0.6707 | 0.050* | |
C21 | 0.0300 (3) | 0.08074 (19) | 0.69569 (9) | 0.0389 (6) | |
C22 | 0.0483 (4) | −0.0313 (2) | 0.72088 (9) | 0.0466 (6) | |
C23 | −0.2430 (4) | −0.0001 (3) | 0.71016 (13) | 0.0636 (8) | |
H23A | −0.3410 | 0.0054 | 0.7332 | 0.076* | |
H23B | −0.2844 | −0.0292 | 0.6780 | 0.076* | |
C24 | −0.1576 (4) | 0.1144 (2) | 0.70334 (10) | 0.0465 (6) | |
H24 | −0.2047 | 0.1558 | 0.6743 | 0.056* | |
C25 | 0.5639 (4) | 0.4780 (2) | 0.46701 (10) | 0.0566 (7) | |
H25A | 0.5465 | 0.5171 | 0.4356 | 0.085* | |
H25B | 0.5833 | 0.3988 | 0.4605 | 0.085* | |
H25C | 0.6633 | 0.5093 | 0.4841 | 0.085* | |
C26 | 0.1885 (3) | 0.49167 (19) | 0.61121 (10) | 0.0477 (6) | |
H26A | 0.1569 | 0.5538 | 0.5896 | 0.072* | |
H26B | 0.2814 | 0.5148 | 0.6332 | 0.072* | |
H26C | 0.0894 | 0.4695 | 0.6310 | 0.072* | |
C27 | 0.4432 (4) | 0.3187 (2) | 0.69820 (10) | 0.0538 (7) | |
H27A | 0.5423 | 0.3400 | 0.7161 | 0.065* | |
H27B | 0.3420 | 0.2991 | 0.7154 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.04786 (14) | 0.06360 (18) | 0.05976 (17) | −0.01636 (14) | −0.00361 (15) | 0.00277 (15) |
O1 | 0.0651 (12) | 0.0290 (8) | 0.0350 (9) | −0.0052 (8) | −0.0084 (8) | 0.0026 (7) |
O2 | 0.0587 (11) | 0.0292 (8) | 0.0405 (9) | −0.0094 (8) | −0.0145 (8) | 0.0081 (7) |
O3 | 0.0839 (16) | 0.0363 (11) | 0.0764 (14) | −0.0098 (11) | 0.0205 (12) | 0.0063 (10) |
O4 | 0.0875 (15) | 0.0456 (11) | 0.0673 (13) | 0.0166 (12) | 0.0032 (12) | 0.0133 (9) |
O5 | 0.0670 (12) | 0.0449 (10) | 0.0684 (12) | −0.0004 (11) | 0.0231 (11) | −0.0058 (9) |
C1 | 0.0449 (14) | 0.0356 (12) | 0.0338 (12) | −0.0026 (11) | 0.0006 (11) | −0.0004 (10) |
C2 | 0.0554 (16) | 0.0503 (15) | 0.0367 (13) | 0.0077 (13) | −0.0121 (12) | −0.0013 (12) |
C3 | 0.0752 (18) | 0.0469 (13) | 0.0310 (11) | −0.0034 (17) | 0.0008 (13) | 0.0068 (12) |
C4 | 0.0578 (16) | 0.0529 (15) | 0.0433 (13) | −0.0078 (16) | 0.0063 (13) | 0.0075 (13) |
C5 | 0.0411 (13) | 0.0450 (13) | 0.0446 (13) | −0.0033 (13) | −0.0009 (12) | 0.0069 (11) |
C6 | 0.0458 (13) | 0.0285 (11) | 0.0344 (11) | −0.0004 (9) | −0.0002 (12) | −0.0008 (10) |
C7 | 0.0460 (13) | 0.0291 (11) | 0.0352 (11) | −0.0009 (11) | −0.0036 (10) | 0.0006 (10) |
C8 | 0.0582 (15) | 0.0236 (11) | 0.0372 (13) | −0.0038 (11) | −0.0067 (12) | 0.0029 (10) |
C9 | 0.0426 (14) | 0.0499 (15) | 0.0537 (16) | −0.0127 (13) | −0.0135 (13) | 0.0138 (13) |
C10 | 0.0446 (13) | 0.0459 (14) | 0.0538 (15) | −0.0116 (12) | −0.0064 (11) | 0.0161 (13) |
C11 | 0.0360 (12) | 0.0291 (11) | 0.0333 (12) | 0.0020 (10) | 0.0023 (10) | 0.0024 (9) |
C12 | 0.0397 (12) | 0.0300 (11) | 0.0370 (13) | 0.0033 (9) | 0.0068 (10) | 0.0039 (9) |
C13 | 0.0433 (13) | 0.0314 (12) | 0.0387 (13) | 0.0068 (11) | −0.0010 (11) | 0.0064 (10) |
C14 | 0.0377 (12) | 0.0575 (15) | 0.0477 (14) | 0.0070 (13) | −0.0024 (10) | 0.0114 (13) |
C15 | 0.0369 (13) | 0.0484 (14) | 0.0474 (14) | −0.0015 (12) | −0.0008 (11) | 0.0133 (12) |
C16 | 0.0353 (11) | 0.0299 (11) | 0.0335 (12) | 0.0033 (10) | 0.0038 (10) | 0.0029 (9) |
C17 | 0.0380 (12) | 0.0316 (12) | 0.0322 (12) | 0.0001 (10) | 0.0029 (10) | 0.0054 (10) |
C18 | 0.0516 (14) | 0.0324 (12) | 0.0380 (12) | −0.0067 (11) | −0.0138 (11) | 0.0033 (10) |
C19 | 0.0450 (15) | 0.0427 (13) | 0.0458 (14) | 0.0036 (12) | 0.0087 (12) | 0.0147 (11) |
C20 | 0.0453 (13) | 0.0399 (13) | 0.0403 (12) | 0.0091 (13) | 0.0051 (12) | 0.0069 (10) |
C21 | 0.0509 (15) | 0.0337 (13) | 0.0322 (12) | −0.0003 (12) | 0.0027 (11) | 0.0015 (10) |
C22 | 0.0696 (19) | 0.0321 (13) | 0.0381 (13) | 0.0019 (14) | 0.0074 (14) | 0.0000 (11) |
C23 | 0.0619 (19) | 0.0562 (18) | 0.073 (2) | −0.0153 (16) | 0.0031 (17) | 0.0009 (16) |
C24 | 0.0505 (15) | 0.0429 (13) | 0.0462 (14) | −0.0030 (13) | 0.0034 (13) | 0.0075 (11) |
C25 | 0.0555 (17) | 0.0600 (17) | 0.0542 (17) | 0.0079 (14) | 0.0157 (14) | 0.0164 (14) |
C26 | 0.0566 (15) | 0.0386 (12) | 0.0480 (14) | 0.0129 (12) | 0.0133 (14) | 0.0034 (11) |
C27 | 0.0639 (17) | 0.0542 (17) | 0.0432 (15) | 0.0007 (15) | −0.0018 (14) | 0.0031 (12) |
Geometric parameters (Å, º) top
Br1—C1 | 1.908 (2) | C12—C19 | 1.524 (3) |
O1—C7 | 1.422 (3) | C12—H12 | 0.98 |
O1—C8 | 1.446 (3) | C13—C27 | 1.332 (3) |
O2—C7 | 1.404 (3) | C13—C14 | 1.500 (3) |
O2—C18 | 1.435 (3) | C14—C15 | 1.529 (3) |
O3—C22 | 1.329 (3) | C14—H14A | 0.97 |
O3—C23 | 1.452 (4) | C14—H14B | 0.97 |
O4—C22 | 1.208 (3) | C15—C16 | 1.527 (3) |
O5—C24 | 1.418 (3) | C15—H15A | 0.97 |
O5—H5A | 0.82 | C15—H15B | 0.97 |
C1—C6 | 1.380 (3) | C16—C17 | 1.561 (3) |
C1—C2 | 1.385 (3) | C16—H16 | 0.98 |
C2—C3 | 1.380 (4) | C17—C25 | 1.534 (3) |
C2—H2 | 0.93 | C17—C18 | 1.534 (3) |
C3—C4 | 1.370 (4) | C18—H18A | 0.97 |
C3—H3 | 0.93 | C18—H18B | 0.97 |
C4—C5 | 1.377 (3) | C19—C20 | 1.505 (3) |
C4—H4 | 0.93 | C19—H19A | 0.97 |
C5—C6 | 1.394 (3) | C19—H19B | 0.97 |
C5—H5 | 0.93 | C20—C21 | 1.319 (3) |
C6—C7 | 1.509 (3) | C20—H20 | 0.93 |
C7—H7 | 0.98 | C21—C22 | 1.485 (4) |
C8—C9 | 1.512 (4) | C21—C24 | 1.507 (4) |
C8—C17 | 1.527 (3) | C23—C24 | 1.510 (4) |
C8—H8 | 0.98 | C23—H23A | 0.97 |
C9—C10 | 1.535 (3) | C23—H23B | 0.97 |
C9—H9A | 0.97 | C24—H24 | 0.98 |
C9—H9B | 0.97 | C25—H25A | 0.96 |
C10—C11 | 1.540 (3) | C25—H25B | 0.96 |
C10—H10A | 0.97 | C25—H25C | 0.96 |
C10—H10B | 0.97 | C26—H26A | 0.96 |
C11—C26 | 1.529 (3) | C26—H26B | 0.96 |
C11—C16 | 1.561 (3) | C26—H26C | 0.96 |
C11—C12 | 1.574 (3) | C27—H27A | 0.93 |
C12—C13 | 1.518 (3) | C27—H27B | 0.93 |
| | | |
C7—O1—C8 | 112.62 (16) | C16—C15—C14 | 110.7 (2) |
C7—O2—C18 | 109.88 (17) | C16—C15—H15A | 109.5 |
C22—O3—C23 | 110.2 (2) | C14—C15—H15A | 109.5 |
C24—O5—H5A | 109.5 | C16—C15—H15B | 109.5 |
C6—C1—C2 | 122.5 (2) | C14—C15—H15B | 109.5 |
C6—C1—Br1 | 120.34 (17) | H15A—C15—H15B | 108.1 |
C2—C1—Br1 | 117.19 (19) | C15—C16—C17 | 113.02 (19) |
C3—C2—C1 | 118.3 (2) | C15—C16—C11 | 111.47 (17) |
C3—C2—H2 | 120.9 | C17—C16—C11 | 117.64 (18) |
C1—C2—H2 | 120.9 | C15—C16—H16 | 104.4 |
C4—C3—C2 | 121.0 (2) | C17—C16—H16 | 104.4 |
C4—C3—H3 | 119.5 | C11—C16—H16 | 104.4 |
C2—C3—H3 | 119.5 | C8—C17—C25 | 108.12 (19) |
C3—C4—C5 | 119.7 (3) | C8—C17—C18 | 107.79 (19) |
C3—C4—H4 | 120.1 | C25—C17—C18 | 107.0 (2) |
C5—C4—H4 | 120.1 | C8—C17—C16 | 109.93 (18) |
C4—C5—C6 | 121.2 (3) | C25—C17—C16 | 109.54 (19) |
C4—C5—H5 | 119.4 | C18—C17—C16 | 114.25 (18) |
C6—C5—H5 | 119.4 | O2—C18—C17 | 110.29 (19) |
C1—C6—C5 | 117.3 (2) | O2—C18—H18A | 109.6 |
C1—C6—C7 | 122.0 (2) | C17—C18—H18A | 109.6 |
C5—C6—C7 | 120.7 (2) | O2—C18—H18B | 109.6 |
O2—C7—O1 | 111.52 (19) | C17—C18—H18B | 109.6 |
O2—C7—C6 | 109.29 (18) | H18A—C18—H18B | 108.1 |
O1—C7—C6 | 106.96 (17) | C20—C19—C12 | 115.4 (2) |
O2—C7—H7 | 109.7 | C20—C19—H19A | 108.4 |
O1—C7—H7 | 109.7 | C12—C19—H19A | 108.4 |
C6—C7—H7 | 109.7 | C20—C19—H19B | 108.4 |
O1—C8—C9 | 112.2 (2) | C12—C19—H19B | 108.4 |
O1—C8—C17 | 110.46 (18) | H19A—C19—H19B | 107.5 |
C9—C8—C17 | 114.84 (19) | C21—C20—C19 | 124.2 (2) |
O1—C8—H8 | 106.2 | C21—C20—H20 | 117.9 |
C9—C8—H8 | 106.2 | C19—C20—H20 | 117.9 |
C17—C8—H8 | 106.2 | C20—C21—C22 | 125.2 (2) |
C8—C9—C10 | 110.2 (2) | C20—C21—C24 | 129.5 (2) |
C8—C9—H9A | 109.6 | C22—C21—C24 | 105.3 (2) |
C10—C9—H9A | 109.6 | O4—C22—O3 | 121.4 (2) |
C8—C9—H9B | 109.6 | O4—C22—C21 | 129.0 (3) |
C10—C9—H9B | 109.6 | O3—C22—C21 | 109.6 (2) |
H9A—C9—H9B | 108.1 | O3—C23—C24 | 105.6 (2) |
C9—C10—C11 | 113.5 (2) | O3—C23—H23A | 110.6 |
C9—C10—H10A | 108.9 | C24—C23—H23A | 110.6 |
C11—C10—H10A | 108.9 | O3—C23—H23B | 110.6 |
C9—C10—H10B | 108.9 | C24—C23—H23B | 110.6 |
C11—C10—H10B | 108.9 | H23A—C23—H23B | 108.8 |
H10A—C10—H10B | 107.7 | O5—C24—C21 | 111.0 (2) |
C26—C11—C10 | 109.9 (2) | O5—C24—C23 | 107.3 (2) |
C26—C11—C16 | 114.80 (19) | C21—C24—C23 | 101.3 (2) |
C10—C11—C16 | 107.29 (18) | O5—C24—H24 | 112.2 |
C26—C11—C12 | 108.41 (18) | C21—C24—H24 | 112.2 |
C10—C11—C12 | 109.62 (18) | C23—C24—H24 | 112.2 |
C16—C11—C12 | 106.76 (17) | C17—C25—H25A | 109.5 |
C13—C12—C19 | 113.32 (19) | C17—C25—H25B | 109.5 |
C13—C12—C11 | 109.69 (18) | H25A—C25—H25B | 109.5 |
C19—C12—C11 | 114.03 (18) | C17—C25—H25C | 109.5 |
C13—C12—H12 | 106.4 | H25A—C25—H25C | 109.5 |
C19—C12—H12 | 106.4 | H25B—C25—H25C | 109.5 |
C11—C12—H12 | 106.4 | C11—C26—H26A | 109.5 |
C27—C13—C14 | 121.1 (2) | C11—C26—H26B | 109.5 |
C27—C13—C12 | 124.1 (2) | H26A—C26—H26B | 109.5 |
C14—C13—C12 | 114.77 (19) | C11—C26—H26C | 109.5 |
C13—C14—C15 | 111.2 (2) | H26A—C26—H26C | 109.5 |
C13—C14—H14A | 109.4 | H26B—C26—H26C | 109.5 |
C15—C14—H14A | 109.4 | C13—C27—H27A | 120.0 |
C13—C14—H14B | 109.4 | C13—C27—H27B | 120.0 |
C15—C14—H14B | 109.4 | H27A—C27—H27B | 120.0 |
H14A—C14—H14B | 108.0 | | |
| | | |
C6—C1—C2—C3 | 1.2 (4) | C14—C15—C16—C11 | 58.9 (3) |
Br1—C1—C2—C3 | −179.37 (19) | C26—C11—C16—C15 | 59.6 (3) |
C1—C2—C3—C4 | −0.3 (4) | C10—C11—C16—C15 | −177.98 (19) |
C2—C3—C4—C5 | −0.3 (4) | C12—C11—C16—C15 | −60.5 (2) |
C3—C4—C5—C6 | 0.0 (4) | C26—C11—C16—C17 | −73.2 (3) |
C2—C1—C6—C5 | −1.4 (4) | C10—C11—C16—C17 | 49.2 (3) |
Br1—C1—C6—C5 | 179.13 (17) | C12—C11—C16—C17 | 166.61 (18) |
C2—C1—C6—C7 | 179.4 (2) | O1—C8—C17—C25 | −64.0 (2) |
Br1—C1—C6—C7 | −0.1 (3) | C9—C8—C17—C25 | 167.8 (2) |
C4—C5—C6—C1 | 0.8 (4) | O1—C8—C17—C18 | 51.3 (2) |
C4—C5—C6—C7 | −180.0 (2) | C9—C8—C17—C18 | −76.8 (2) |
C18—O2—C7—O1 | −62.6 (2) | O1—C8—C17—C16 | 176.45 (18) |
C18—O2—C7—C6 | 179.38 (18) | C9—C8—C17—C16 | 48.3 (3) |
C8—O1—C7—O2 | 59.7 (2) | C15—C16—C17—C8 | −178.5 (2) |
C8—O1—C7—C6 | 179.16 (18) | C11—C16—C17—C8 | −46.3 (3) |
C1—C6—C7—O2 | −163.0 (2) | C15—C16—C17—C25 | 62.8 (3) |
C5—C6—C7—O2 | 17.8 (3) | C11—C16—C17—C25 | −165.0 (2) |
C1—C6—C7—O1 | 76.1 (3) | C15—C16—C17—C18 | −57.2 (3) |
C5—C6—C7—O1 | −103.1 (2) | C11—C16—C17—C18 | 75.0 (3) |
C7—O1—C8—C9 | 75.2 (2) | C7—O2—C18—C17 | 61.3 (2) |
C7—O1—C8—C17 | −54.3 (3) | C8—C17—C18—O2 | −55.4 (2) |
O1—C8—C9—C10 | 177.19 (19) | C25—C17—C18—O2 | 60.7 (3) |
C17—C8—C9—C10 | −55.5 (3) | C16—C17—C18—O2 | −177.92 (18) |
C8—C9—C10—C11 | 59.4 (3) | C13—C12—C19—C20 | −66.3 (3) |
C9—C10—C11—C26 | 70.9 (3) | C11—C12—C19—C20 | 167.3 (2) |
C9—C10—C11—C16 | −54.6 (3) | C12—C19—C20—C21 | −173.8 (2) |
C9—C10—C11—C12 | −170.1 (2) | C19—C20—C21—C22 | 178.7 (2) |
C26—C11—C12—C13 | −66.7 (2) | C19—C20—C21—C24 | −0.2 (4) |
C10—C11—C12—C13 | 173.36 (18) | C23—O3—C22—O4 | −177.3 (3) |
C16—C11—C12—C13 | 57.5 (2) | C23—O3—C22—C21 | 4.5 (3) |
C26—C11—C12—C19 | 61.6 (3) | C20—C21—C22—O4 | 16.8 (4) |
C10—C11—C12—C19 | −58.3 (3) | C24—C21—C22—O4 | −164.2 (3) |
C16—C11—C12—C19 | −174.23 (19) | C20—C21—C22—O3 | −165.3 (2) |
C19—C12—C13—C27 | −7.7 (3) | C24—C21—C22—O3 | 13.8 (3) |
C11—C12—C13—C27 | 121.0 (2) | C22—O3—C23—C24 | −21.0 (3) |
C19—C12—C13—C14 | 175.03 (19) | C20—C21—C24—O5 | −92.2 (3) |
C11—C12—C13—C14 | −56.3 (3) | C22—C21—C24—O5 | 88.8 (2) |
C27—C13—C14—C15 | −124.2 (2) | C20—C21—C24—C23 | 154.1 (3) |
C12—C13—C14—C15 | 53.1 (3) | C22—C21—C24—C23 | −24.9 (3) |
C13—C14—C15—C16 | −52.8 (3) | O3—C23—C24—O5 | −88.8 (3) |
C14—C15—C16—C17 | −166.0 (2) | O3—C23—C24—C21 | 27.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O4i | 0.82 | 2.20 | 2.909 (3) | 145 |
C2—H2···O5ii | 0.93 | 2.41 | 3.318 (4) | 164 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x−1/2, −y+1, z−1/2. |