Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
25H
31NO
4, was synthesized by the reaction of dimedone with 4-hydroxy-3-methoxybenzaldehyde and CH
3NH
2HCl(NaOAc) in glycol. X-ray analysis reveals that the dihydropyridine ring is in a distorted-boat conformation. O—H
O hydrogen bonds involving the hydroxy and carbonyl O atoms link glide-related molecules into zigzag chains along the
c axis.
Supporting information
CCDC reference: 253031
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.108
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C25 .. 6.83 su
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
9-(4-Hydroxy-3-methyoxyphenyl)-3,3,6,6,10-pentamethyl-1,2,3,4,5,6,7,8,9,10-
decahydroacridine-1,8-dione
top
Crystal data top
C25H31NO4 | F(000) = 880 |
Mr = 409.51 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Melting point = 522–523 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.640 (2) Å | Cell parameters from 41 reflections |
b = 14.884 (2) Å | θ = 3.7–15.2° |
c = 13.604 (2) Å | µ = 0.09 mm−1 |
β = 91.15 (1)° | T = 295 K |
V = 2154.0 (6) Å3 | Block, yellow |
Z = 4 | 0.58 × 0.30 × 0.22 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.015 |
Radiation source: normal-focus sealed tube | θmax = 25.3°, θmin = 1.9° |
Graphite monochromator | h = 0→12 |
ω scans | k = 0→17 |
4445 measured reflections | l = −16→16 |
3899 independent reflections | 3 standard reflections every 97 reflections |
2409 reflections with I > 2σ(I) | intensity decay: 3.4% |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
3899 reflections | Δρmax = 0.18 e Å−3 |
279 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0075 (9) |
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 | |
O1 | 0.36976 (13) | 0.43463 (10) | 0.02554 (10) | 0.0516 (4) | |
O2 | 0.73554 (12) | 0.38486 (10) | 0.23334 (11) | 0.0529 (4) | |
O3 | 0.22405 (13) | 0.15163 (10) | 0.39116 (11) | 0.0540 (4) | |
H3O | 0.2700 | 0.1235 | 0.4293 | 0.065* | |
O4 | 0.10489 (12) | 0.25260 (10) | 0.26167 (11) | 0.0556 (4) | |
N1 | 0.44284 (14) | 0.61237 (10) | 0.30682 (11) | 0.0329 (4) | |
C1 | 0.37393 (17) | 0.59243 (12) | 0.22204 (13) | 0.0312 (4) | |
C2 | 0.27655 (18) | 0.65910 (12) | 0.18813 (15) | 0.0419 (5) | |
H2A | 0.3189 | 0.7142 | 0.1701 | 0.050* | |
H2B | 0.2230 | 0.6728 | 0.2430 | 0.050* | |
C3 | 0.19330 (19) | 0.62924 (13) | 0.10138 (14) | 0.0426 (5) | |
C4 | 0.2742 (2) | 0.57990 (15) | 0.02757 (15) | 0.0535 (6) | |
H4A | 0.2203 | 0.5560 | −0.0245 | 0.064* | |
H4B | 0.3314 | 0.6224 | −0.0018 | 0.064* | |
C5 | 0.34902 (17) | 0.50441 (13) | 0.07256 (14) | 0.0375 (5) | |
C6 | 0.39888 (16) | 0.51602 (11) | 0.17121 (13) | 0.0311 (4) | |
C7 | 0.48269 (16) | 0.44461 (11) | 0.21507 (13) | 0.0310 (4) | |
H7 | 0.5247 | 0.4151 | 0.1603 | 0.037* | |
C8 | 0.58323 (16) | 0.49097 (12) | 0.27558 (13) | 0.0314 (4) | |
C9 | 0.71064 (18) | 0.45495 (13) | 0.27699 (14) | 0.0384 (5) | |
C10 | 0.81091 (19) | 0.50785 (15) | 0.33050 (16) | 0.0487 (6) | |
H10A | 0.8446 | 0.5523 | 0.2861 | 0.058* | |
H10B | 0.8789 | 0.4676 | 0.3495 | 0.058* | |
C11 | 0.76399 (18) | 0.55524 (14) | 0.42176 (15) | 0.0429 (5) | |
C12 | 0.65133 (18) | 0.61390 (13) | 0.39190 (15) | 0.0419 (5) | |
H12A | 0.6086 | 0.6324 | 0.4509 | 0.050* | |
H12B | 0.6821 | 0.6677 | 0.3601 | 0.050* | |
C13 | 0.55786 (17) | 0.56887 (12) | 0.32400 (13) | 0.0320 (4) | |
C14 | 0.41126 (16) | 0.37113 (11) | 0.27048 (13) | 0.0311 (4) | |
C15 | 0.46935 (18) | 0.31944 (12) | 0.34254 (14) | 0.0364 (5) | |
H15 | 0.5505 | 0.3338 | 0.3638 | 0.044* | |
C16 | 0.40834 (18) | 0.24606 (13) | 0.38403 (14) | 0.0392 (5) | |
H16 | 0.4499 | 0.2119 | 0.4318 | 0.047* | |
C17 | 0.28763 (17) | 0.22344 (12) | 0.35539 (14) | 0.0360 (5) | |
C18 | 0.22622 (17) | 0.27730 (13) | 0.28580 (14) | 0.0370 (5) | |
C19 | 0.28808 (17) | 0.34885 (12) | 0.24364 (14) | 0.0359 (5) | |
H19 | 0.2463 | 0.3831 | 0.1960 | 0.043* | |
C20 | 0.0326 (2) | 0.31353 (16) | 0.2042 (2) | 0.0705 (8) | |
H20A | 0.0296 | 0.3706 | 0.2370 | 0.085* | |
H20B | −0.0512 | 0.2906 | 0.1955 | 0.085* | |
H20C | 0.0703 | 0.3208 | 0.1412 | 0.085* | |
C21 | 0.0886 (2) | 0.56812 (15) | 0.1377 (2) | 0.0678 (7) | |
H21A | 0.0426 | 0.5439 | 0.0824 | 0.081* | |
H21B | 0.0329 | 0.6021 | 0.1780 | 0.081* | |
H21C | 0.1247 | 0.5199 | 0.1756 | 0.081* | |
C22 | 0.1343 (2) | 0.71285 (16) | 0.05335 (18) | 0.0707 (8) | |
H22A | 0.1996 | 0.7518 | 0.0307 | 0.085* | |
H22B | 0.0847 | 0.7441 | 0.1006 | 0.085* | |
H22C | 0.0816 | 0.6950 | −0.0013 | 0.085* | |
C23 | 0.8685 (2) | 0.61519 (17) | 0.46528 (18) | 0.0678 (7) | |
H23A | 0.9392 | 0.5786 | 0.4846 | 0.081* | |
H23B | 0.8378 | 0.6464 | 0.5217 | 0.081* | |
H23C | 0.8940 | 0.6580 | 0.4168 | 0.081* | |
C24 | 0.7253 (2) | 0.48726 (16) | 0.49951 (17) | 0.0588 (6) | |
H24A | 0.6546 | 0.4532 | 0.4753 | 0.071* | |
H24B | 0.7028 | 0.5184 | 0.5584 | 0.071* | |
H24C | 0.7943 | 0.4474 | 0.5137 | 0.071* | |
C25 | 0.4111 (2) | 0.69286 (13) | 0.36509 (16) | 0.0545 (6) | |
H25A | 0.4612 | 0.7427 | 0.3442 | 0.065* | |
H25B | 0.4279 | 0.6812 | 0.4335 | 0.065* | |
H25C | 0.3237 | 0.7069 | 0.3554 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0559 (9) | 0.0509 (9) | 0.0477 (9) | 0.0053 (8) | −0.0107 (7) | −0.0178 (7) |
O2 | 0.0386 (8) | 0.0489 (9) | 0.0710 (10) | 0.0101 (7) | −0.0014 (7) | −0.0166 (8) |
O3 | 0.0453 (9) | 0.0502 (9) | 0.0660 (11) | −0.0131 (8) | −0.0116 (7) | 0.0232 (8) |
O4 | 0.0334 (8) | 0.0566 (9) | 0.0761 (11) | −0.0110 (7) | −0.0162 (7) | 0.0236 (8) |
N1 | 0.0397 (9) | 0.0269 (8) | 0.0321 (8) | 0.0044 (7) | −0.0004 (7) | −0.0054 (7) |
C1 | 0.0317 (10) | 0.0274 (10) | 0.0347 (10) | 0.0002 (8) | 0.0031 (8) | 0.0034 (8) |
C2 | 0.0448 (12) | 0.0297 (11) | 0.0513 (13) | 0.0039 (9) | 0.0022 (10) | 0.0025 (10) |
C3 | 0.0413 (12) | 0.0415 (12) | 0.0448 (12) | 0.0074 (10) | −0.0050 (10) | 0.0039 (10) |
C4 | 0.0609 (15) | 0.0595 (14) | 0.0398 (12) | 0.0113 (12) | −0.0098 (11) | 0.0018 (11) |
C5 | 0.0333 (11) | 0.0413 (12) | 0.0378 (11) | −0.0018 (9) | 0.0009 (9) | −0.0016 (10) |
C6 | 0.0308 (10) | 0.0284 (10) | 0.0342 (11) | −0.0006 (8) | 0.0024 (8) | 0.0007 (9) |
C7 | 0.0306 (10) | 0.0278 (10) | 0.0346 (10) | 0.0031 (8) | 0.0011 (8) | −0.0047 (8) |
C8 | 0.0316 (10) | 0.0286 (10) | 0.0340 (11) | −0.0019 (8) | 0.0006 (8) | 0.0002 (8) |
C9 | 0.0357 (11) | 0.0386 (12) | 0.0411 (12) | 0.0013 (10) | 0.0036 (9) | −0.0002 (10) |
C10 | 0.0316 (11) | 0.0554 (14) | 0.0590 (14) | −0.0051 (10) | −0.0021 (10) | −0.0052 (11) |
C11 | 0.0397 (12) | 0.0454 (12) | 0.0434 (12) | −0.0063 (10) | −0.0058 (10) | −0.0044 (10) |
C12 | 0.0468 (12) | 0.0357 (11) | 0.0430 (12) | −0.0074 (10) | −0.0033 (10) | −0.0036 (10) |
C13 | 0.0356 (11) | 0.0281 (10) | 0.0324 (10) | −0.0043 (8) | 0.0018 (9) | 0.0021 (8) |
C14 | 0.0308 (10) | 0.0246 (10) | 0.0380 (11) | 0.0023 (8) | −0.0007 (8) | −0.0053 (8) |
C15 | 0.0314 (10) | 0.0324 (10) | 0.0452 (12) | −0.0003 (9) | −0.0063 (9) | −0.0022 (9) |
C16 | 0.0409 (11) | 0.0348 (11) | 0.0416 (12) | 0.0024 (10) | −0.0077 (9) | 0.0037 (9) |
C17 | 0.0360 (11) | 0.0310 (10) | 0.0410 (11) | −0.0045 (9) | 0.0001 (9) | 0.0022 (9) |
C18 | 0.0294 (10) | 0.0374 (11) | 0.0440 (12) | −0.0024 (9) | −0.0034 (9) | 0.0024 (9) |
C19 | 0.0335 (11) | 0.0317 (11) | 0.0423 (12) | 0.0012 (9) | −0.0061 (9) | 0.0039 (9) |
C20 | 0.0383 (13) | 0.0743 (17) | 0.098 (2) | −0.0064 (13) | −0.0209 (13) | 0.0292 (16) |
C21 | 0.0409 (13) | 0.0595 (16) | 0.103 (2) | 0.0003 (12) | −0.0043 (13) | −0.0032 (15) |
C22 | 0.0757 (18) | 0.0701 (17) | 0.0657 (16) | 0.0295 (15) | −0.0114 (14) | 0.0135 (14) |
C23 | 0.0562 (15) | 0.0732 (17) | 0.0733 (18) | −0.0118 (13) | −0.0162 (13) | −0.0177 (14) |
C24 | 0.0635 (16) | 0.0617 (15) | 0.0507 (14) | 0.0036 (13) | −0.0074 (12) | 0.0065 (12) |
C25 | 0.0710 (15) | 0.0426 (13) | 0.0497 (13) | 0.0133 (12) | −0.0009 (12) | −0.0088 (11) |
Geometric parameters (Å, º) top
O1—C5 | 1.242 (2) | C11—C12 | 1.531 (3) |
O2—C9 | 1.232 (2) | C11—C23 | 1.535 (3) |
O3—C17 | 1.360 (2) | C12—C13 | 1.501 (2) |
O3—H3O | 0.82 | C12—H12A | 0.97 |
O4—C18 | 1.376 (2) | C12—H12B | 0.97 |
O4—C20 | 1.415 (2) | C14—C15 | 1.382 (2) |
N1—C1 | 1.386 (2) | C14—C19 | 1.394 (2) |
N1—C13 | 1.400 (2) | C15—C16 | 1.395 (3) |
N1—C25 | 1.479 (2) | C15—H15 | 0.93 |
C1—C6 | 1.360 (2) | C16—C17 | 1.376 (3) |
C1—C2 | 1.501 (2) | C16—H16 | 0.93 |
C2—C3 | 1.527 (3) | C17—C18 | 1.393 (3) |
C2—H2A | 0.97 | C18—C19 | 1.383 (3) |
C2—H2B | 0.97 | C19—H19 | 0.93 |
C3—C4 | 1.524 (3) | C20—H20A | 0.96 |
C3—C21 | 1.528 (3) | C20—H20B | 0.96 |
C3—C22 | 1.534 (3) | C20—H20C | 0.96 |
C4—C5 | 1.500 (3) | C21—H21A | 0.96 |
C4—H4A | 0.97 | C21—H21B | 0.96 |
C4—H4B | 0.97 | C21—H21C | 0.96 |
C5—C6 | 1.444 (3) | C22—H22A | 0.96 |
C6—C7 | 1.503 (2) | C22—H22B | 0.96 |
C7—C8 | 1.504 (2) | C22—H22C | 0.96 |
C7—C14 | 1.538 (2) | C23—H23A | 0.96 |
C7—H7 | 0.98 | C23—H23B | 0.96 |
C8—C13 | 1.363 (2) | C23—H23C | 0.96 |
C8—C9 | 1.458 (3) | C24—H24A | 0.96 |
C9—C10 | 1.502 (3) | C24—H24B | 0.96 |
C10—C11 | 1.521 (3) | C24—H24C | 0.96 |
C10—H10A | 0.97 | C25—H25A | 0.96 |
C10—H10B | 0.97 | C25—H25B | 0.96 |
C11—C24 | 1.526 (3) | C25—H25C | 0.96 |
| | | |
C17—O3—H3O | 109.5 | C11—C12—H12B | 108.6 |
C18—O4—C20 | 117.25 (16) | H12A—C12—H12B | 107.6 |
C1—N1—C13 | 119.07 (14) | C8—C13—N1 | 119.57 (16) |
C1—N1—C25 | 119.77 (16) | C8—C13—C12 | 122.81 (17) |
C13—N1—C25 | 119.55 (16) | N1—C13—C12 | 117.53 (15) |
C6—C1—N1 | 119.78 (16) | C15—C14—C19 | 117.27 (17) |
C6—C1—C2 | 122.50 (17) | C15—C14—C7 | 121.68 (16) |
N1—C1—C2 | 117.68 (15) | C19—C14—C7 | 120.81 (16) |
C1—C2—C3 | 115.55 (16) | C14—C15—C16 | 121.16 (17) |
C1—C2—H2A | 108.4 | C14—C15—H15 | 119.4 |
C3—C2—H2A | 108.4 | C16—C15—H15 | 119.4 |
C1—C2—H2B | 108.4 | C17—C16—C15 | 121.06 (18) |
C3—C2—H2B | 108.4 | C17—C16—H16 | 119.5 |
H2A—C2—H2B | 107.5 | C15—C16—H16 | 119.5 |
C4—C3—C2 | 108.84 (16) | O3—C17—C16 | 123.97 (18) |
C4—C3—C21 | 110.56 (18) | O3—C17—C18 | 117.74 (17) |
C2—C3—C21 | 109.77 (18) | C16—C17—C18 | 118.29 (17) |
C4—C3—C22 | 110.00 (18) | O4—C18—C19 | 124.00 (17) |
C2—C3—C22 | 108.61 (17) | O4—C18—C17 | 115.69 (17) |
C21—C3—C22 | 109.04 (18) | C19—C18—C17 | 120.29 (17) |
C5—C4—C3 | 113.21 (17) | C18—C19—C14 | 121.84 (17) |
C5—C4—H4A | 108.9 | C18—C19—H19 | 119.1 |
C3—C4—H4A | 108.9 | C14—C19—H19 | 119.1 |
C5—C4—H4B | 108.9 | O4—C20—H20A | 109.5 |
C3—C4—H4B | 108.9 | O4—C20—H20B | 109.5 |
H4A—C4—H4B | 107.7 | H20A—C20—H20B | 109.5 |
O1—C5—C6 | 120.87 (17) | O4—C20—H20C | 109.5 |
O1—C5—C4 | 120.97 (18) | H20A—C20—H20C | 109.5 |
C6—C5—C4 | 118.15 (17) | H20B—C20—H20C | 109.5 |
C1—C6—C5 | 120.06 (17) | C3—C21—H21A | 109.5 |
C1—C6—C7 | 120.65 (16) | C3—C21—H21B | 109.5 |
C5—C6—C7 | 119.24 (16) | H21A—C21—H21B | 109.5 |
C6—C7—C8 | 107.61 (14) | C3—C21—H21C | 109.5 |
C6—C7—C14 | 113.72 (14) | H21A—C21—H21C | 109.5 |
C8—C7—C14 | 114.27 (15) | H21B—C21—H21C | 109.5 |
C6—C7—H7 | 106.9 | C3—C22—H22A | 109.5 |
C8—C7—H7 | 106.9 | C3—C22—H22B | 109.5 |
C14—C7—H7 | 106.9 | H22A—C22—H22B | 109.5 |
C13—C8—C9 | 119.97 (17) | C3—C22—H22C | 109.5 |
C13—C8—C7 | 120.61 (16) | H22A—C22—H22C | 109.5 |
C9—C8—C7 | 119.30 (16) | H22B—C22—H22C | 109.5 |
O2—C9—C8 | 120.94 (18) | C11—C23—H23A | 109.5 |
O2—C9—C10 | 121.33 (18) | C11—C23—H23B | 109.5 |
C8—C9—C10 | 117.70 (17) | H23A—C23—H23B | 109.5 |
C9—C10—C11 | 113.40 (17) | C11—C23—H23C | 109.5 |
C9—C10—H10A | 108.9 | H23A—C23—H23C | 109.5 |
C11—C10—H10A | 108.9 | H23B—C23—H23C | 109.5 |
C9—C10—H10B | 108.9 | C11—C24—H24A | 109.5 |
C11—C10—H10B | 108.9 | C11—C24—H24B | 109.5 |
H10A—C10—H10B | 107.7 | H24A—C24—H24B | 109.5 |
C10—C11—C24 | 110.83 (17) | C11—C24—H24C | 109.5 |
C10—C11—C12 | 108.42 (16) | H24A—C24—H24C | 109.5 |
C24—C11—C12 | 109.97 (17) | H24B—C24—H24C | 109.5 |
C10—C11—C23 | 109.71 (18) | N1—C25—H25A | 109.5 |
C24—C11—C23 | 108.73 (18) | N1—C25—H25B | 109.5 |
C12—C11—C23 | 109.16 (17) | H25A—C25—H25B | 109.5 |
C13—C12—C11 | 114.46 (16) | N1—C25—H25C | 109.5 |
C13—C12—H12A | 108.6 | H25A—C25—H25C | 109.5 |
C11—C12—H12A | 108.6 | H25B—C25—H25C | 109.5 |
C13—C12—H12B | 108.6 | | |
| | | |
C13—N1—C1—C6 | 17.9 (2) | C9—C10—C11—C24 | 65.8 (2) |
C25—N1—C1—C6 | −176.65 (17) | C9—C10—C11—C12 | −55.0 (2) |
C13—N1—C1—C2 | −159.99 (16) | C9—C10—C11—C23 | −174.10 (18) |
C25—N1—C1—C2 | 5.5 (2) | C10—C11—C12—C13 | 44.5 (2) |
C6—C1—C2—C3 | 8.9 (3) | C24—C11—C12—C13 | −76.8 (2) |
N1—C1—C2—C3 | −173.35 (16) | C23—C11—C12—C13 | 163.98 (17) |
C1—C2—C3—C4 | −40.3 (2) | C9—C8—C13—N1 | 167.45 (16) |
C1—C2—C3—C21 | 80.8 (2) | C7—C8—C13—N1 | −8.6 (3) |
C1—C2—C3—C22 | −160.09 (18) | C9—C8—C13—C12 | −9.1 (3) |
C2—C3—C4—C5 | 53.3 (2) | C7—C8—C13—C12 | 174.86 (16) |
C21—C3—C4—C5 | −67.3 (2) | C1—N1—C13—C8 | −19.3 (2) |
C22—C3—C4—C5 | 172.23 (18) | C25—N1—C13—C8 | 175.16 (17) |
C3—C4—C5—O1 | 145.32 (19) | C1—N1—C13—C12 | 157.39 (16) |
C3—C4—C5—C6 | −36.2 (3) | C25—N1—C13—C12 | −8.1 (2) |
N1—C1—C6—C5 | −165.92 (16) | C11—C12—C13—C8 | −13.9 (3) |
C2—C1—C6—C5 | 11.8 (3) | C11—C12—C13—N1 | 169.49 (16) |
N1—C1—C6—C7 | 11.5 (3) | C6—C7—C14—C15 | −156.98 (16) |
C2—C1—C6—C7 | −170.75 (16) | C8—C7—C14—C15 | −32.9 (2) |
O1—C5—C6—C1 | −179.20 (18) | C6—C7—C14—C19 | 28.8 (2) |
C4—C5—C6—C1 | 2.3 (3) | C8—C7—C14—C19 | 152.87 (16) |
O1—C5—C6—C7 | 3.3 (3) | C19—C14—C15—C16 | 2.2 (3) |
C4—C5—C6—C7 | −175.18 (17) | C7—C14—C15—C16 | −172.25 (16) |
C1—C6—C7—C8 | −34.9 (2) | C14—C15—C16—C17 | −0.8 (3) |
C5—C6—C7—C8 | 142.51 (16) | C15—C16—C17—O3 | 178.38 (18) |
C1—C6—C7—C14 | 92.7 (2) | C15—C16—C17—C18 | −1.9 (3) |
C5—C6—C7—C14 | −89.9 (2) | C20—O4—C18—C19 | −12.0 (3) |
C6—C7—C8—C13 | 33.4 (2) | C20—O4—C18—C17 | 169.7 (2) |
C14—C7—C8—C13 | −94.0 (2) | O3—C17—C18—O4 | 1.2 (3) |
C6—C7—C8—C9 | −142.73 (17) | C16—C17—C18—O4 | −178.60 (17) |
C14—C7—C8—C9 | 90.0 (2) | O3—C17—C18—C19 | −177.14 (18) |
C13—C8—C9—O2 | −179.69 (18) | C16—C17—C18—C19 | 3.1 (3) |
C7—C8—C9—O2 | −3.6 (3) | O4—C18—C19—C14 | −179.89 (18) |
C13—C8—C9—C10 | −1.7 (3) | C17—C18—C19—C14 | −1.7 (3) |
C7—C8—C9—C10 | 174.38 (17) | C15—C14—C19—C18 | −0.9 (3) |
O2—C9—C10—C11 | −147.0 (2) | C7—C14—C19—C18 | 173.55 (16) |
C8—C9—C10—C11 | 35.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O1i | 0.82 | 1.88 | 2.698 (2) | 175 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.