In the title compound, C
23H
27NO
4, a modified synthetic
D-homo steroid, the cyclohexene ring adjacent to the aromatic ring adopts a half-chair conformation, while the cyclohexane ring has an ideal chair conformation and the heterocyclic ring has a sofa conformation. The plane of the allyl substituent lies almost perpendicular to the least-squares plane of the heterocyclic ring. The crystal structure contains a series of weak C—H
O intermolecular interactions.
Supporting information
CCDC reference: 262483
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.128
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. CG1 .. 2.99 Ang.
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 27.48
From the CIF: _reflns_number_total 2596
Count of symmetry unique reflns 2599
Completeness (_total/calc) 99.88%
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
2 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: PLEASE PROVIDE; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
17-allyl-16,17
a-dioxo-17-aza-D-homoestra-1,3,5(10)-trien-3-yl acetate
top
Crystal data top
C23H27NO4 | F(000) = 816 |
Mr = 381.46 | Dx = 1.270 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2614 reflections |
a = 9.3546 (2) Å | θ = 2.0–27.5° |
b = 10.7074 (2) Å | µ = 0.09 mm−1 |
c = 19.9204 (5) Å | T = 160 K |
V = 1995.30 (8) Å3 | Tablet, colourless |
Z = 4 | 0.25 × 0.18 × 0.10 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2063 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed tube generator | Rint = 0.068 |
Horizontally mounted graphite crystal monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 9 pixels mm-1 | h = −12→12 |
φ and ω scans with κ offsets | k = −13→13 |
30780 measured reflections | l = −25→25 |
2596 independent 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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1695P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.004 |
2591 reflections | Δρmax = 0.25 e Å−3 |
256 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (3) |
Special details top
Experimental. Solvent used: methanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal
mount: glued on a glass fibre Mosaicity (°.): 0.435 (2) Frames collected: 247
Seconds exposure per frame: 90 Degrees rotation per frame: 1.8
Crystal-Detector distance (mm): 30.0 |
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 | |
O16 | −0.1852 (2) | 0.07213 (18) | 0.51999 (10) | 0.0566 (6) | |
O17A | 0.0686 (2) | −0.12972 (16) | 0.36185 (10) | 0.0506 (5) | |
O31 | 0.38829 (19) | 0.78490 (16) | 0.20927 (8) | 0.0391 (4) | |
O32 | 0.3554 (2) | 0.7728 (2) | 0.09810 (9) | 0.0578 (6) | |
N17 | −0.0626 (2) | −0.02694 (19) | 0.43862 (10) | 0.0354 (5) | |
C1 | 0.3033 (3) | 0.4467 (2) | 0.20939 (13) | 0.0381 (6) | |
H1 | 0.3269 | 0.3723 | 0.1859 | 0.046* | |
C2 | 0.3636 (3) | 0.5586 (2) | 0.18849 (13) | 0.0399 (6) | |
H2 | 0.4274 | 0.5610 | 0.1514 | 0.048* | |
C3 | 0.3290 (3) | 0.6660 (2) | 0.22273 (12) | 0.0341 (6) | |
C4 | 0.2348 (3) | 0.6631 (2) | 0.27598 (12) | 0.0333 (5) | |
H4 | 0.2116 | 0.7384 | 0.2987 | 0.040* | |
C5 | 0.1734 (3) | 0.5508 (2) | 0.29679 (12) | 0.0328 (5) | |
C6 | 0.0723 (3) | 0.5543 (2) | 0.35577 (13) | 0.0395 (6) | |
H61 | 0.0046 | 0.6245 | 0.3497 | 0.047* | |
H62 | 0.1278 | 0.5705 | 0.3972 | 0.047* | |
C7 | −0.0117 (3) | 0.4347 (2) | 0.36457 (13) | 0.0366 (6) | |
H71 | −0.0869 | 0.4293 | 0.3297 | 0.044* | |
H72 | −0.0587 | 0.4344 | 0.4091 | 0.044* | |
C8 | 0.0884 (3) | 0.3226 (2) | 0.35878 (11) | 0.0284 (5) | |
H8 | 0.1722 | 0.3377 | 0.3889 | 0.034* | |
C9 | 0.1437 (3) | 0.3156 (2) | 0.28585 (12) | 0.0326 (5) | |
H9 | 0.0591 | 0.2997 | 0.2564 | 0.039* | |
C10 | 0.2087 (3) | 0.4396 (2) | 0.26390 (11) | 0.0319 (5) | |
C11 | 0.2452 (3) | 0.2040 (2) | 0.27792 (14) | 0.0402 (6) | |
H111 | 0.2736 | 0.1966 | 0.2302 | 0.048* | |
H112 | 0.3327 | 0.2193 | 0.3046 | 0.048* | |
C12 | 0.1780 (3) | 0.0823 (2) | 0.30039 (13) | 0.0378 (6) | |
H121 | 0.2497 | 0.0147 | 0.2968 | 0.045* | |
H122 | 0.0977 | 0.0616 | 0.2700 | 0.045* | |
C13 | 0.1221 (3) | 0.0881 (2) | 0.37327 (11) | 0.0306 (5) | |
C14 | 0.0193 (3) | 0.1990 (2) | 0.37951 (11) | 0.0285 (5) | |
H14 | −0.0621 | 0.1834 | 0.3481 | 0.034* | |
C15 | −0.0418 (3) | 0.2020 (2) | 0.45055 (11) | 0.0351 (6) | |
H151 | 0.0348 | 0.2270 | 0.4821 | 0.042* | |
H152 | −0.1176 | 0.2664 | 0.4526 | 0.042* | |
C16 | −0.1030 (3) | 0.0803 (2) | 0.47322 (12) | 0.0390 (6) | |
C17A | 0.0420 (3) | −0.0311 (2) | 0.38860 (13) | 0.0354 (6) | |
C18 | 0.2485 (3) | 0.0929 (2) | 0.42361 (14) | 0.0414 (6) | |
H181 | 0.2114 | 0.0905 | 0.4696 | 0.062* | |
H182 | 0.3027 | 0.1702 | 0.4169 | 0.062* | |
H183 | 0.3113 | 0.0210 | 0.4162 | 0.062* | |
C19 | −0.1305 (3) | −0.1461 (3) | 0.45737 (14) | 0.0459 (7) | |
H191 | −0.1481 | −0.1962 | 0.4164 | 0.055* | |
H192 | −0.2240 | −0.1291 | 0.4788 | 0.055* | |
C20 | −0.0389 (4) | −0.2194 (3) | 0.50471 (16) | 0.0585 (8) | |
H20 | 0.0561 | −0.2372 | 0.4909 | 0.070* | |
C21 | −0.0785 (5) | −0.2602 (3) | 0.56264 (18) | 0.0743 (10) | |
H211 | −0.1727 | −0.2444 | 0.5783 | 0.089* | |
H212 | −0.0135 | −0.3062 | 0.5897 | 0.089* | |
C31 | 0.3913 (3) | 0.8318 (2) | 0.14637 (13) | 0.0384 (6) | |
C32 | 0.4437 (3) | 0.9625 (3) | 0.14636 (15) | 0.0494 (7) | |
H321 | 0.5457 | 0.9635 | 0.1351 | 0.074* | |
H322 | 0.4297 | 0.9991 | 0.1910 | 0.074* | |
H323 | 0.3905 | 1.0111 | 0.1130 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O16 | 0.0725 (13) | 0.0450 (11) | 0.0523 (11) | 0.0111 (11) | 0.0310 (11) | 0.0094 (9) |
O17A | 0.0623 (13) | 0.0316 (9) | 0.0580 (12) | −0.0033 (9) | 0.0173 (11) | −0.0121 (9) |
O31 | 0.0433 (10) | 0.0384 (9) | 0.0356 (9) | −0.0054 (8) | 0.0024 (8) | 0.0024 (8) |
O32 | 0.0742 (15) | 0.0606 (12) | 0.0386 (11) | −0.0130 (12) | −0.0052 (10) | 0.0030 (10) |
N17 | 0.0381 (11) | 0.0314 (10) | 0.0366 (10) | −0.0012 (9) | 0.0038 (9) | 0.0003 (9) |
C1 | 0.0408 (14) | 0.0371 (13) | 0.0365 (13) | −0.0007 (12) | 0.0080 (11) | −0.0053 (11) |
C2 | 0.0387 (14) | 0.0441 (15) | 0.0370 (13) | −0.0008 (12) | 0.0096 (11) | −0.0012 (11) |
C3 | 0.0328 (13) | 0.0349 (12) | 0.0347 (12) | −0.0031 (11) | −0.0017 (11) | 0.0029 (11) |
C4 | 0.0352 (13) | 0.0349 (12) | 0.0299 (12) | 0.0012 (11) | −0.0017 (10) | 0.0006 (10) |
C5 | 0.0323 (12) | 0.0350 (12) | 0.0311 (12) | 0.0020 (11) | −0.0009 (10) | 0.0000 (10) |
C6 | 0.0477 (15) | 0.0313 (13) | 0.0394 (13) | 0.0038 (12) | 0.0098 (12) | 0.0000 (11) |
C7 | 0.0404 (13) | 0.0344 (13) | 0.0351 (12) | 0.0036 (11) | 0.0096 (11) | 0.0045 (11) |
C8 | 0.0301 (11) | 0.0307 (12) | 0.0243 (11) | 0.0020 (10) | 0.0006 (9) | −0.0018 (9) |
C9 | 0.0324 (13) | 0.0356 (12) | 0.0298 (12) | −0.0016 (11) | 0.0018 (10) | −0.0050 (10) |
C10 | 0.0275 (12) | 0.0376 (13) | 0.0307 (12) | −0.0019 (11) | 0.0003 (9) | −0.0010 (10) |
C11 | 0.0410 (14) | 0.0360 (13) | 0.0438 (14) | 0.0014 (12) | 0.0141 (12) | −0.0078 (12) |
C12 | 0.0398 (14) | 0.0339 (12) | 0.0398 (13) | −0.0023 (11) | 0.0114 (11) | −0.0114 (11) |
C13 | 0.0309 (11) | 0.0280 (11) | 0.0328 (12) | 0.0005 (10) | 0.0019 (10) | −0.0049 (10) |
C14 | 0.0290 (11) | 0.0300 (12) | 0.0265 (11) | 0.0014 (10) | 0.0000 (9) | −0.0020 (10) |
C15 | 0.0419 (14) | 0.0326 (12) | 0.0309 (12) | 0.0067 (11) | 0.0075 (11) | 0.0004 (10) |
C16 | 0.0433 (14) | 0.0403 (13) | 0.0334 (13) | 0.0055 (13) | 0.0060 (11) | 0.0036 (11) |
C17A | 0.0355 (13) | 0.0343 (13) | 0.0362 (12) | −0.0003 (11) | 0.0030 (11) | −0.0034 (11) |
C18 | 0.0369 (13) | 0.0367 (13) | 0.0506 (15) | 0.0024 (12) | −0.0071 (12) | −0.0034 (12) |
C19 | 0.0479 (16) | 0.0411 (14) | 0.0487 (15) | −0.0084 (13) | 0.0049 (14) | 0.0022 (13) |
C20 | 0.067 (2) | 0.0462 (17) | 0.0627 (19) | −0.0030 (16) | 0.0002 (16) | 0.0071 (17) |
C21 | 0.085 (2) | 0.066 (2) | 0.072 (2) | −0.008 (2) | −0.002 (2) | 0.0180 (19) |
C31 | 0.0312 (13) | 0.0470 (15) | 0.0369 (13) | 0.0026 (11) | 0.0023 (11) | 0.0041 (12) |
C32 | 0.0519 (16) | 0.0480 (16) | 0.0483 (16) | −0.0060 (14) | 0.0049 (14) | 0.0108 (13) |
Geometric parameters (Å, º) top
O16—C16 | 1.211 (3) | C9—H9 | 1.0000 |
O17A—C17A | 1.209 (3) | C11—C12 | 1.514 (3) |
O31—C31 | 1.350 (3) | C11—H111 | 0.9900 |
O31—C3 | 1.415 (3) | C11—H112 | 0.9900 |
O32—C31 | 1.199 (3) | C12—C13 | 1.544 (3) |
N17—C16 | 1.391 (3) | C12—H121 | 0.9900 |
N17—C17A | 1.397 (3) | C12—H122 | 0.9900 |
N17—C19 | 1.474 (3) | C13—C17A | 1.512 (3) |
C1—C2 | 1.389 (4) | C13—C14 | 1.532 (3) |
C1—C10 | 1.403 (3) | C13—C18 | 1.552 (3) |
C1—H1 | 0.9500 | C14—C15 | 1.527 (3) |
C2—C3 | 1.375 (4) | C14—H14 | 1.0000 |
C2—H2 | 0.9500 | C15—C16 | 1.493 (4) |
C3—C4 | 1.379 (3) | C15—H151 | 0.9900 |
C4—C5 | 1.396 (3) | C15—H152 | 0.9900 |
C4—H4 | 0.9500 | C18—H181 | 0.9800 |
C5—C10 | 1.399 (3) | C18—H182 | 0.9800 |
C5—C6 | 1.509 (3) | C18—H183 | 0.9800 |
C6—C7 | 1.513 (3) | C19—C20 | 1.496 (4) |
C6—H61 | 0.9900 | C19—H191 | 0.9900 |
C6—H62 | 0.9900 | C19—H192 | 0.9900 |
C7—C8 | 1.527 (3) | C20—C21 | 1.288 (5) |
C7—H71 | 0.9900 | C20—H20 | 0.9500 |
C7—H72 | 0.9900 | C21—H211 | 0.9500 |
C8—C14 | 1.529 (3) | C21—H212 | 0.9500 |
C8—C9 | 1.544 (3) | C31—C32 | 1.482 (4) |
C8—H8 | 1.0000 | C32—H321 | 0.9800 |
C9—C10 | 1.524 (3) | C32—H322 | 0.9800 |
C9—C11 | 1.535 (3) | C32—H323 | 0.9800 |
| | | |
C31—O31—C3 | 121.3 (2) | C11—C12—H122 | 109.1 |
C16—N17—C17A | 124.7 (2) | C13—C12—H122 | 109.1 |
C16—N17—C19 | 118.15 (19) | H121—C12—H122 | 107.8 |
C17A—N17—C19 | 117.1 (2) | C17A—C13—C14 | 109.09 (18) |
C2—C1—C10 | 122.4 (2) | C17A—C13—C12 | 108.90 (19) |
C2—C1—H1 | 118.8 | C14—C13—C12 | 108.65 (19) |
C10—C1—H1 | 118.8 | C17A—C13—C18 | 105.97 (19) |
C3—C2—C1 | 118.5 (2) | C14—C13—C18 | 113.59 (19) |
C3—C2—H2 | 120.8 | C12—C13—C18 | 110.5 (2) |
C1—C2—H2 | 120.8 | C15—C14—C8 | 112.99 (18) |
C2—C3—C4 | 120.9 (2) | C15—C14—C13 | 109.05 (19) |
C2—C3—O31 | 124.5 (2) | C8—C14—C13 | 112.55 (18) |
C4—C3—O31 | 114.6 (2) | C15—C14—H14 | 107.3 |
C3—C4—C5 | 120.7 (2) | C8—C14—H14 | 107.3 |
C3—C4—H4 | 119.7 | C13—C14—H14 | 107.3 |
C5—C4—H4 | 119.7 | C16—C15—C14 | 113.9 (2) |
C4—C5—C10 | 119.8 (2) | C16—C15—H151 | 108.8 |
C4—C5—C6 | 117.9 (2) | C14—C15—H151 | 108.8 |
C10—C5—C6 | 122.3 (2) | C16—C15—H152 | 108.8 |
C5—C6—C7 | 113.2 (2) | C14—C15—H152 | 108.8 |
C5—C6—H61 | 108.9 | H151—C15—H152 | 107.7 |
C7—C6—H61 | 108.9 | O16—C16—N17 | 119.6 (2) |
C5—C6—H62 | 108.9 | O16—C16—C15 | 122.6 (2) |
C7—C6—H62 | 108.9 | N17—C16—C15 | 117.8 (2) |
H61—C6—H62 | 107.7 | O17A—C17A—N17 | 119.1 (2) |
C6—C7—C8 | 109.8 (2) | O17A—C17A—C13 | 123.1 (2) |
C6—C7—H71 | 109.7 | N17—C17A—C13 | 117.7 (2) |
C8—C7—H71 | 109.7 | C13—C18—H181 | 109.5 |
C6—C7—H72 | 109.7 | C13—C18—H182 | 109.5 |
C8—C7—H72 | 109.7 | H181—C18—H182 | 109.5 |
H71—C7—H72 | 108.2 | C13—C18—H183 | 109.5 |
C7—C8—C14 | 113.63 (19) | H181—C18—H183 | 109.5 |
C7—C8—C9 | 108.33 (18) | H182—C18—H183 | 109.5 |
C14—C8—C9 | 110.71 (18) | N17—C19—C20 | 111.5 (2) |
C7—C8—H8 | 108.0 | N17—C19—H191 | 109.3 |
C14—C8—H8 | 108.0 | C20—C19—H191 | 109.3 |
C9—C8—H8 | 108.0 | N17—C19—H192 | 109.3 |
C10—C9—C11 | 113.69 (19) | C20—C19—H192 | 109.3 |
C10—C9—C8 | 111.20 (18) | H191—C19—H192 | 108.0 |
C11—C9—C8 | 110.0 (2) | C21—C20—C19 | 125.3 (3) |
C10—C9—H9 | 107.2 | C21—C20—H20 | 117.4 |
C11—C9—H9 | 107.2 | C19—C20—H20 | 117.4 |
C8—C9—H9 | 107.2 | C20—C21—H211 | 120.0 |
C5—C10—C1 | 117.7 (2) | C20—C21—H212 | 120.0 |
C5—C10—C9 | 120.8 (2) | H211—C21—H212 | 120.0 |
C1—C10—C9 | 121.4 (2) | O32—C31—O31 | 122.8 (2) |
C12—C11—C9 | 112.5 (2) | O32—C31—C32 | 126.2 (2) |
C12—C11—H111 | 109.1 | O31—C31—C32 | 111.0 (2) |
C9—C11—H111 | 109.1 | C31—C32—H321 | 109.5 |
C12—C11—H112 | 109.1 | C31—C32—H322 | 109.5 |
C9—C11—H112 | 109.1 | H321—C32—H322 | 109.5 |
H111—C11—H112 | 107.8 | C31—C32—H323 | 109.5 |
C11—C12—C13 | 112.6 (2) | H321—C32—H323 | 109.5 |
C11—C12—H121 | 109.1 | H322—C32—H323 | 109.5 |
C13—C12—H121 | 109.1 | | |
| | | |
C10—C1—C2—C3 | 0.0 (4) | C7—C8—C14—C15 | −55.9 (3) |
C1—C2—C3—C4 | −0.9 (4) | C9—C8—C14—C15 | −178.07 (19) |
C1—C2—C3—O31 | 176.4 (2) | C7—C8—C14—C13 | −179.97 (19) |
C31—O31—C3—C2 | 50.6 (3) | C9—C8—C14—C13 | 57.9 (2) |
C31—O31—C3—C4 | −131.9 (2) | C17A—C13—C14—C15 | 58.8 (2) |
C2—C3—C4—C5 | 0.6 (4) | C12—C13—C14—C15 | 177.43 (19) |
O31—C3—C4—C5 | −177.0 (2) | C18—C13—C14—C15 | −59.1 (3) |
C3—C4—C5—C10 | 0.7 (4) | C17A—C13—C14—C8 | −174.95 (19) |
C3—C4—C5—C6 | 179.5 (2) | C12—C13—C14—C8 | −56.4 (2) |
C4—C5—C6—C7 | 167.6 (2) | C18—C13—C14—C8 | 67.1 (2) |
C10—C5—C6—C7 | −13.7 (4) | C8—C14—C15—C16 | −177.0 (2) |
C5—C6—C7—C8 | 46.4 (3) | C13—C14—C15—C16 | −51.0 (3) |
C6—C7—C8—C14 | 169.5 (2) | C17A—N17—C16—O16 | −173.2 (2) |
C6—C7—C8—C9 | −67.0 (3) | C19—N17—C16—O16 | 4.5 (4) |
C7—C8—C9—C10 | 53.1 (3) | C17A—N17—C16—C15 | 6.8 (4) |
C14—C8—C9—C10 | 178.29 (19) | C19—N17—C16—C15 | −175.5 (2) |
C7—C8—C9—C11 | 179.91 (19) | C14—C15—C16—O16 | −161.6 (2) |
C14—C8—C9—C11 | −54.9 (3) | C14—C15—C16—N17 | 18.4 (3) |
C4—C5—C10—C1 | −1.6 (4) | C16—N17—C17A—O17A | 179.9 (2) |
C6—C5—C10—C1 | 179.7 (2) | C19—N17—C17A—O17A | 2.3 (4) |
C4—C5—C10—C9 | 179.7 (2) | C16—N17—C17A—C13 | 3.1 (4) |
C6—C5—C10—C9 | 1.0 (4) | C19—N17—C17A—C13 | −174.5 (2) |
C2—C1—C10—C5 | 1.2 (4) | C14—C13—C17A—O17A | 146.9 (3) |
C2—C1—C10—C9 | 179.9 (2) | C12—C13—C17A—O17A | 28.5 (3) |
C11—C9—C10—C5 | −145.9 (2) | C18—C13—C17A—O17A | −90.4 (3) |
C8—C9—C10—C5 | −21.2 (3) | C14—C13—C17A—N17 | −36.4 (3) |
C11—C9—C10—C1 | 35.4 (3) | C12—C13—C17A—N17 | −154.8 (2) |
C8—C9—C10—C1 | 160.2 (2) | C18—C13—C17A—N17 | 86.2 (2) |
C10—C9—C11—C12 | 179.7 (2) | C3—O31—C31—O32 | −6.2 (4) |
C8—C9—C11—C12 | 54.3 (3) | C3—O31—C31—C32 | 173.8 (2) |
C9—C11—C12—C13 | −55.4 (3) | C16—N17—C19—C20 | −97.2 (3) |
C11—C12—C13—C17A | 173.5 (2) | C17A—N17—C19—C20 | 80.6 (3) |
C11—C12—C13—C14 | 54.7 (3) | N17—C19—C20—C21 | 124.8 (3) |
C11—C12—C13—C18 | −70.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O17Ai | 0.95 | 2.32 | 3.204 (3) | 155 |
C8—H8···O16ii | 1.00 | 2.45 | 3.404 (3) | 159 |
C15—H151···O32iii | 0.99 | 2.53 | 3.428 (3) | 151 |
C15—H152···O32iv | 0.99 | 2.44 | 3.181 (3) | 131 |
C14—H14···Cg1iv | 1.00 | 2.99 | 3.591 (3) | 162 |
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1/2, −y+1, z+1/2; (iv) −x, y−1/2, −z+1/2. |