In the title compound, C
27H
25NO
5, the pyran ring in the chroman-4-one moiety adopts a sofa conformation and the pyrrolidine ring adopts a twisted or half-chair conformation. The chromanone moiety makes a dihedral angle of 64.3 (1)° with the mean plane passing through the pyrrolidine ring. In the crystal structure, the molecular packing is stabilized by C—H
O intermolecular interactions.
Supporting information
CCDC reference: 177230
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.128
- Data-to-parameter ratio = 13.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
WEIGH_01 Alert C Extra text has been found in the
_refine_ls_weighting_scheme field. This should be in the
_refine_ls_weighting_details field.
Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.289
Weighting scheme identified as calc
PLAT_420 Alert C D-H Without Acceptor N(1) - H(1) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EEXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983b, 1995).
Spiro[2-carbomethoxy-5-(4-methoxyphenyl)-3-phenylpyrrolidine-4,3'-chroman-
4'-one]
top
Crystal data top
C27H25NO5 | Z = 2 |
Mr = 443.48 | F(000) = 468 |
Triclinic, P1 | Dx = 1.305 Mg m−3 |
a = 6.709 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.958 (5) Å | Cell parameters from 25 reflections |
c = 17.743 (5) Å | θ = 19.7–28.2° |
α = 95.757 (5)° | µ = 0.09 mm−1 |
β = 94.587 (5)° | T = 293 K |
γ = 105.600 (5)° | Prism, colourless |
V = 1128.9 (11) Å3 | 0.3 × 0.2 × 0.2 mm |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.2° |
Graphite monochromator | h = −7→7 |
non–profiled ω/2θ scans | k = −11→11 |
4080 measured reflections | l = 0→21 |
3942 independent reflections | 3 standard reflections every 100 reflections |
2907 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.128 | Calculated w = 1/[σ2(Fo2) + (0.0663P)2 + 0.2895P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3942 reflections | Δρmax = 0.38 e Å−3 |
298 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00 |
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 | |
N1 | 0.5945 (3) | 0.10199 (17) | 0.31080 (11) | 0.0606 (5) | |
H1 | 0.5479 | 0.1508 | 0.3443 | 0.073* | |
O1 | 1.08592 (19) | 0.00170 (15) | 0.18918 (8) | 0.0538 (4) | |
O2 | 0.61071 (19) | 0.14181 (15) | 0.09832 (8) | 0.0560 (4) | |
O3 | 1.5532 (3) | 0.39572 (17) | 0.43084 (9) | 0.0777 (5) | |
O4 | 0.6341 (3) | −0.1343 (2) | 0.40869 (10) | 0.0918 (6) | |
O5 | 0.3010 (3) | −0.1489 (2) | 0.38026 (10) | 0.0889 (6) | |
C1 | 0.9473 (3) | 0.04826 (18) | 0.16500 (10) | 0.0389 (4) | |
C2 | 0.7473 (3) | 0.03427 (18) | 0.20210 (10) | 0.0401 (4) | |
C3 | 0.5740 (3) | 0.0196 (2) | 0.13778 (12) | 0.0492 (5) | |
H3A | 0.5650 | −0.0625 | 0.1019 | 0.059* | |
H3B | 0.4419 | 0.0057 | 0.1588 | 0.059* | |
C4 | 0.8180 (3) | 0.2591 (2) | 0.01203 (11) | 0.0511 (5) | |
H4 | 0.7089 | 0.2941 | −0.0042 | 0.061* | |
C5 | 0.9994 (3) | 0.2909 (2) | −0.02137 (11) | 0.0550 (5) | |
H5 | 1.0133 | 0.3475 | −0.0603 | 0.066* | |
C6 | 1.1617 (3) | 0.2389 (2) | 0.00282 (12) | 0.0551 (5) | |
H6 | 1.2831 | 0.2583 | −0.0209 | 0.066* | |
C7 | 1.1439 (3) | 0.1590 (2) | 0.06164 (11) | 0.0472 (5) | |
H7 | 1.2552 | 0.1261 | 0.0780 | 0.057* | |
C8 | 0.9626 (2) | 0.12586 (18) | 0.09745 (10) | 0.0386 (4) | |
C9 | 0.7977 (3) | 0.17475 (19) | 0.06983 (10) | 0.0417 (4) | |
C10 | 0.7567 (3) | 0.1621 (2) | 0.26265 (12) | 0.0484 (5) | |
H10 | 0.7155 | 0.2345 | 0.2368 | 0.058* | |
C11 | 0.9681 (3) | 0.22694 (19) | 0.30778 (11) | 0.0488 (5) | |
C12 | 1.1155 (3) | 0.3331 (2) | 0.28150 (13) | 0.0576 (5) | |
H12 | 1.0812 | 0.3649 | 0.2360 | 0.069* | |
C13 | 1.3119 (4) | 0.3936 (2) | 0.32033 (13) | 0.0605 (6) | |
H13 | 1.4070 | 0.4650 | 0.3013 | 0.073* | |
C14 | 1.3648 (3) | 0.3466 (2) | 0.38766 (12) | 0.0568 (5) | |
C15 | 1.2208 (4) | 0.2402 (2) | 0.41463 (12) | 0.0647 (6) | |
H15 | 1.2562 | 0.2075 | 0.4597 | 0.078* | |
C16 | 1.0263 (4) | 0.1822 (2) | 0.37585 (11) | 0.0585 (5) | |
H16 | 0.9314 | 0.1116 | 0.3955 | 0.070* | |
C17 | 1.7085 (4) | 0.5026 (3) | 0.40573 (17) | 0.0891 (8) | |
H17A | 1.8318 | 0.5268 | 0.4414 | 0.134* | |
H17B | 1.6592 | 0.5840 | 0.4021 | 0.134* | |
H17C | 1.7401 | 0.4699 | 0.3566 | 0.134* | |
C18 | 0.5230 (3) | −0.0507 (2) | 0.29445 (11) | 0.0472 (5) | |
H18 | 0.3903 | −0.0792 | 0.2616 | 0.057* | |
C19 | 0.4978 (3) | −0.1158 (2) | 0.36737 (12) | 0.0557 (5) | |
C20 | 0.2541 (6) | −0.2060 (5) | 0.45149 (19) | 0.1337 (15) | |
H20A | 0.1074 | −0.2252 | 0.4553 | 0.201* | |
H20B | 0.3297 | −0.1389 | 0.4937 | 0.201* | |
H20C | 0.2943 | −0.2914 | 0.4523 | 0.201* | |
C21 | 0.6936 (3) | −0.08766 (18) | 0.25113 (10) | 0.0405 (4) | |
H21 | 0.8148 | −0.0747 | 0.2886 | 0.049* | |
C22 | 0.6416 (3) | −0.23675 (19) | 0.21189 (10) | 0.0416 (4) | |
C23 | 0.4476 (3) | −0.3071 (2) | 0.17283 (11) | 0.0529 (5) | |
H23 | 0.3438 | −0.2614 | 0.1699 | 0.063* | |
C24 | 0.4065 (4) | −0.4439 (2) | 0.13825 (12) | 0.0634 (6) | |
H24 | 0.2763 | −0.4888 | 0.1119 | 0.076* | |
C25 | 0.5569 (4) | −0.5136 (2) | 0.14263 (14) | 0.0682 (6) | |
H25 | 0.5290 | −0.6056 | 0.1193 | 0.082* | |
C26 | 0.7479 (4) | −0.4470 (2) | 0.18147 (14) | 0.0662 (6) | |
H26 | 0.8499 | −0.4943 | 0.1847 | 0.079* | |
C27 | 0.7913 (3) | −0.3091 (2) | 0.21620 (12) | 0.0532 (5) | |
H27 | 0.9219 | −0.2651 | 0.2425 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0665 (11) | 0.0496 (10) | 0.0751 (12) | 0.0220 (8) | 0.0406 (9) | 0.0101 (9) |
O1 | 0.0386 (7) | 0.0749 (9) | 0.0608 (8) | 0.0298 (7) | 0.0098 (6) | 0.0274 (7) |
O2 | 0.0343 (7) | 0.0762 (9) | 0.0730 (9) | 0.0262 (6) | 0.0166 (6) | 0.0442 (8) |
O3 | 0.0783 (11) | 0.0740 (11) | 0.0668 (10) | 0.0022 (9) | −0.0047 (9) | 0.0063 (8) |
O4 | 0.0818 (12) | 0.1317 (17) | 0.0665 (11) | 0.0217 (11) | 0.0167 (9) | 0.0508 (11) |
O5 | 0.0692 (11) | 0.1239 (15) | 0.0742 (11) | 0.0110 (10) | 0.0363 (9) | 0.0369 (11) |
C1 | 0.0301 (9) | 0.0456 (10) | 0.0443 (10) | 0.0148 (8) | 0.0036 (7) | 0.0100 (8) |
C2 | 0.0342 (9) | 0.0470 (10) | 0.0465 (10) | 0.0189 (8) | 0.0094 (7) | 0.0172 (8) |
C3 | 0.0328 (9) | 0.0641 (12) | 0.0594 (12) | 0.0175 (9) | 0.0114 (8) | 0.0326 (10) |
C4 | 0.0447 (11) | 0.0641 (12) | 0.0506 (11) | 0.0202 (9) | 0.0037 (9) | 0.0233 (10) |
C5 | 0.0534 (12) | 0.0660 (13) | 0.0472 (11) | 0.0124 (10) | 0.0103 (9) | 0.0229 (10) |
C6 | 0.0436 (11) | 0.0703 (13) | 0.0539 (12) | 0.0126 (10) | 0.0201 (9) | 0.0168 (10) |
C7 | 0.0342 (9) | 0.0600 (12) | 0.0508 (11) | 0.0165 (8) | 0.0087 (8) | 0.0109 (9) |
C8 | 0.0318 (9) | 0.0450 (10) | 0.0410 (9) | 0.0128 (7) | 0.0049 (7) | 0.0084 (8) |
C9 | 0.0315 (9) | 0.0515 (10) | 0.0458 (10) | 0.0138 (8) | 0.0072 (7) | 0.0150 (8) |
C10 | 0.0486 (11) | 0.0461 (10) | 0.0609 (12) | 0.0225 (9) | 0.0203 (9) | 0.0186 (9) |
C11 | 0.0569 (12) | 0.0435 (10) | 0.0518 (11) | 0.0193 (9) | 0.0180 (9) | 0.0095 (9) |
C12 | 0.0630 (13) | 0.0531 (12) | 0.0596 (13) | 0.0145 (10) | 0.0110 (10) | 0.0215 (10) |
C13 | 0.0643 (14) | 0.0502 (12) | 0.0657 (14) | 0.0087 (10) | 0.0157 (11) | 0.0148 (10) |
C14 | 0.0664 (14) | 0.0521 (12) | 0.0484 (12) | 0.0130 (10) | 0.0079 (10) | −0.0022 (9) |
C15 | 0.0826 (16) | 0.0658 (14) | 0.0418 (11) | 0.0126 (12) | 0.0086 (11) | 0.0098 (10) |
C16 | 0.0720 (14) | 0.0561 (12) | 0.0443 (11) | 0.0082 (11) | 0.0182 (10) | 0.0090 (9) |
C17 | 0.0740 (17) | 0.0837 (18) | 0.092 (2) | −0.0029 (14) | −0.0026 (15) | 0.0076 (15) |
C18 | 0.0455 (10) | 0.0516 (11) | 0.0498 (11) | 0.0167 (9) | 0.0166 (8) | 0.0129 (9) |
C19 | 0.0591 (13) | 0.0592 (13) | 0.0480 (12) | 0.0105 (10) | 0.0183 (10) | 0.0096 (10) |
C20 | 0.112 (2) | 0.195 (4) | 0.081 (2) | −0.005 (3) | 0.0513 (19) | 0.053 (2) |
C21 | 0.0389 (9) | 0.0475 (10) | 0.0406 (10) | 0.0178 (8) | 0.0073 (7) | 0.0136 (8) |
C22 | 0.0467 (10) | 0.0467 (10) | 0.0381 (9) | 0.0179 (8) | 0.0111 (8) | 0.0174 (8) |
C23 | 0.0594 (13) | 0.0532 (12) | 0.0496 (11) | 0.0194 (10) | 0.0044 (9) | 0.0141 (9) |
C24 | 0.0738 (15) | 0.0545 (13) | 0.0557 (13) | 0.0073 (11) | 0.0035 (11) | 0.0102 (10) |
C25 | 0.0926 (18) | 0.0492 (12) | 0.0653 (14) | 0.0205 (13) | 0.0181 (13) | 0.0101 (11) |
C26 | 0.0792 (16) | 0.0574 (13) | 0.0792 (16) | 0.0378 (12) | 0.0287 (13) | 0.0227 (12) |
C27 | 0.0560 (12) | 0.0533 (12) | 0.0596 (12) | 0.0240 (10) | 0.0154 (10) | 0.0201 (10) |
Geometric parameters (Å, º) top
N1—C18 | 1.457 (3) | C11—C16 | 1.391 (3) |
N1—C10 | 1.474 (2) | C12—C13 | 1.385 (3) |
N1—H1 | 0.860 | C12—H12 | 0.930 |
O1—C1 | 1.213 (2) | C13—C14 | 1.381 (3) |
O2—C9 | 1.360 (2) | C13—H13 | 0.930 |
O2—C3 | 1.438 (2) | C14—C15 | 1.382 (3) |
O3—C14 | 1.364 (3) | C15—C16 | 1.371 (3) |
O3—C17 | 1.411 (3) | C15—H15 | 0.930 |
O4—C19 | 1.191 (3) | C16—H16 | 0.930 |
O5—C19 | 1.317 (3) | C17—H17A | 0.960 |
O5—C20 | 1.460 (3) | C17—H17B | 0.960 |
C1—C8 | 1.486 (2) | C17—H17C | 0.960 |
C1—C2 | 1.521 (2) | C18—C19 | 1.506 (3) |
C2—C3 | 1.529 (3) | C18—C21 | 1.532 (2) |
C2—C21 | 1.545 (2) | C18—H18 | 0.980 |
C2—C10 | 1.565 (3) | C20—H20A | 0.960 |
C3—H3A | 0.970 | C20—H20B | 0.960 |
C3—H3B | 0.970 | C20—H20C | 0.960 |
C4—C5 | 1.370 (3) | C21—C22 | 1.512 (3) |
C4—C9 | 1.382 (3) | C21—H21 | 0.980 |
C4—H4 | 0.930 | C22—C27 | 1.386 (3) |
C5—C6 | 1.382 (3) | C22—C23 | 1.390 (3) |
C5—H5 | 0.930 | C23—C24 | 1.382 (3) |
C6—C7 | 1.368 (3) | C23—H23 | 0.930 |
C6—H6 | 0.930 | C24—C25 | 1.372 (3) |
C7—C8 | 1.394 (3) | C24—H24 | 0.930 |
C7—H7 | 0.930 | C25—C26 | 1.367 (3) |
C8—C9 | 1.397 (2) | C25—H25 | 0.930 |
C10—C11 | 1.514 (3) | C26—C27 | 1.392 (3) |
C10—H10 | 0.980 | C26—H26 | 0.930 |
C11—C12 | 1.387 (3) | C27—H27 | 0.930 |
| | | |
C18—N1—C10 | 111.35 (14) | O3—C14—C13 | 125.1 (2) |
C18—N1—H1 | 124.3 | O3—C14—C15 | 115.7 (2) |
C10—N1—H1 | 124.3 | C13—C14—C15 | 119.2 (2) |
C9—O2—C3 | 113.97 (13) | C16—C15—C14 | 120.9 (2) |
C14—O3—C17 | 118.50 (19) | C16—C15—H15 | 119.6 |
C19—O5—C20 | 116.5 (2) | C14—C15—H15 | 119.6 |
O1—C1—C8 | 122.21 (15) | C15—C16—C11 | 121.4 (2) |
O1—C1—C2 | 122.82 (16) | C15—C16—H16 | 119.3 |
C8—C1—C2 | 114.97 (14) | C11—C16—H16 | 119.3 |
C1—C2—C3 | 106.62 (15) | O3—C17—H17A | 109.5 |
C1—C2—C21 | 114.60 (13) | O3—C17—H17B | 109.5 |
C3—C2—C21 | 111.58 (14) | H17A—C17—H17B | 109.5 |
C1—C2—C10 | 113.52 (14) | O3—C17—H17C | 109.5 |
C3—C2—C10 | 109.97 (14) | H17A—C17—H17C | 109.5 |
C21—C2—C10 | 100.56 (14) | H17B—C17—H17C | 109.5 |
O2—C3—C2 | 111.66 (15) | N1—C18—C19 | 110.35 (16) |
O2—C3—H3A | 109.3 | N1—C18—C21 | 103.59 (14) |
C2—C3—H3A | 109.3 | C19—C18—C21 | 112.89 (16) |
O2—C3—H3B | 109.3 | N1—C18—H18 | 109.9 |
C2—C3—H3B | 109.3 | C19—C18—H18 | 109.9 |
H3A—C3—H3B | 107.9 | C21—C18—H18 | 109.9 |
C5—C4—C9 | 119.83 (17) | O4—C19—O5 | 123.9 (2) |
C5—C4—H4 | 120.1 | O4—C19—C18 | 125.90 (19) |
C9—C4—H4 | 120.1 | O5—C19—C18 | 110.22 (19) |
C4—C5—C6 | 120.05 (19) | O5—C20—H20A | 109.5 |
C4—C5—H5 | 120.0 | O5—C20—H20B | 109.5 |
C6—C5—H5 | 120.0 | H20A—C20—H20B | 109.5 |
C7—C6—C5 | 120.11 (17) | O5—C20—H20C | 109.5 |
C7—C6—H6 | 119.9 | H20A—C20—H20C | 109.5 |
C5—C6—H6 | 119.9 | H20B—C20—H20C | 109.5 |
C6—C7—C8 | 121.34 (17) | C22—C21—C18 | 115.78 (15) |
C6—C7—H7 | 119.3 | C22—C21—C2 | 118.47 (15) |
C8—C7—H7 | 119.3 | C18—C21—C2 | 101.17 (13) |
C7—C8—C9 | 117.41 (16) | C22—C21—H21 | 106.9 |
C7—C8—C1 | 121.77 (15) | C18—C21—H21 | 106.9 |
C9—C8—C1 | 120.75 (15) | C2—C21—H21 | 106.9 |
O2—C9—C4 | 117.03 (15) | C27—C22—C23 | 117.80 (19) |
O2—C9—C8 | 121.81 (16) | C27—C22—C21 | 119.09 (17) |
C4—C9—C8 | 121.16 (16) | C23—C22—C21 | 123.09 (16) |
N1—C10—C11 | 112.75 (17) | C24—C23—C22 | 121.1 (2) |
N1—C10—C2 | 102.88 (14) | C24—C23—H23 | 119.4 |
C11—C10—C2 | 114.37 (14) | C22—C23—H23 | 119.4 |
N1—C10—H10 | 108.9 | C25—C24—C23 | 120.3 (2) |
C11—C10—H10 | 108.9 | C25—C24—H24 | 119.8 |
C2—C10—H10 | 108.9 | C23—C24—H24 | 119.8 |
C12—C11—C16 | 116.8 (2) | C26—C25—C24 | 119.6 (2) |
C12—C11—C10 | 120.70 (18) | C26—C25—H25 | 120.2 |
C16—C11—C10 | 122.50 (18) | C24—C25—H25 | 120.2 |
C13—C12—C11 | 122.6 (2) | C25—C26—C27 | 120.6 (2) |
C13—C12—H12 | 118.7 | C25—C26—H26 | 119.7 |
C11—C12—H12 | 118.7 | C27—C26—H26 | 119.7 |
C14—C13—C12 | 119.2 (2) | C22—C27—C26 | 120.6 (2) |
C14—C13—H13 | 120.4 | C22—C27—H27 | 119.7 |
C12—C13—H13 | 120.4 | C26—C27—H27 | 119.7 |
| | | |
O1—C1—C2—C3 | −146.52 (18) | C11—C12—C13—C14 | 0.4 (3) |
C8—C1—C2—C3 | 34.6 (2) | C17—O3—C14—C13 | −0.2 (3) |
O1—C1—C2—C21 | −22.5 (3) | C17—O3—C14—C15 | 178.9 (2) |
C8—C1—C2—C21 | 158.57 (15) | C12—C13—C14—O3 | 179.1 (2) |
O1—C1—C2—C10 | 92.2 (2) | C12—C13—C14—C15 | 0.1 (3) |
C8—C1—C2—C10 | −86.65 (18) | O3—C14—C15—C16 | −179.8 (2) |
C9—O2—C3—C2 | 55.8 (2) | C13—C14—C15—C16 | −0.6 (3) |
C1—C2—C3—O2 | −61.75 (19) | C14—C15—C16—C11 | 0.8 (3) |
C21—C2—C3—O2 | 172.43 (14) | C12—C11—C16—C15 | −0.4 (3) |
C10—C2—C3—O2 | 61.72 (19) | C10—C11—C16—C15 | 178.25 (19) |
C9—C4—C5—C6 | −0.1 (3) | C10—N1—C18—C19 | 137.83 (18) |
C4—C5—C6—C7 | −1.9 (3) | C10—N1—C18—C21 | 16.7 (2) |
C5—C6—C7—C8 | 1.2 (3) | C20—O5—C19—O4 | 2.7 (4) |
C6—C7—C8—C9 | 1.4 (3) | C20—O5—C19—C18 | −176.6 (2) |
C6—C7—C8—C1 | −175.37 (18) | N1—C18—C19—O4 | −80.5 (3) |
O1—C1—C8—C7 | −5.1 (3) | C21—C18—C19—O4 | 34.9 (3) |
C2—C1—C8—C7 | 173.82 (17) | N1—C18—C19—O5 | 98.8 (2) |
O1—C1—C8—C9 | 178.24 (18) | C21—C18—C19—O5 | −145.81 (18) |
C2—C1—C8—C9 | −2.9 (2) | N1—C18—C21—C22 | −167.61 (15) |
C3—O2—C9—C4 | 159.82 (18) | C19—C18—C21—C22 | 73.0 (2) |
C3—O2—C9—C8 | −20.1 (3) | N1—C18—C21—C2 | −38.19 (18) |
C5—C4—C9—O2 | −177.13 (18) | C19—C18—C21—C2 | −157.56 (16) |
C5—C4—C9—C8 | 2.8 (3) | C1—C2—C21—C22 | −65.7 (2) |
C7—C8—C9—O2 | 176.51 (17) | C3—C2—C21—C22 | 55.6 (2) |
C1—C8—C9—O2 | −6.7 (3) | C10—C2—C21—C22 | 172.19 (15) |
C7—C8—C9—C4 | −3.4 (3) | C1—C2—C21—C18 | 166.62 (15) |
C1—C8—C9—C4 | 173.38 (18) | C3—C2—C21—C18 | −72.09 (19) |
C18—N1—C10—C11 | −112.19 (18) | C10—C2—C21—C18 | 44.49 (16) |
C18—N1—C10—C2 | 11.5 (2) | C18—C21—C22—C27 | −137.40 (18) |
C1—C2—C10—N1 | −157.43 (15) | C2—C21—C22—C27 | 102.15 (19) |
C3—C2—C10—N1 | 83.23 (18) | C18—C21—C22—C23 | 40.9 (2) |
C21—C2—C10—N1 | −34.54 (17) | C2—C21—C22—C23 | −79.5 (2) |
C1—C2—C10—C11 | −34.8 (2) | C27—C22—C23—C24 | −1.2 (3) |
C3—C2—C10—C11 | −154.15 (15) | C21—C22—C23—C24 | −179.51 (18) |
C21—C2—C10—C11 | 88.08 (17) | C22—C23—C24—C25 | 0.7 (3) |
N1—C10—C11—C12 | −154.38 (17) | C23—C24—C25—C26 | 0.0 (3) |
C2—C10—C11—C12 | 88.5 (2) | C24—C25—C26—C27 | −0.3 (3) |
N1—C10—C11—C16 | 27.1 (2) | C23—C22—C27—C26 | 0.9 (3) |
C2—C10—C11—C16 | −90.0 (2) | C21—C22—C27—C26 | 179.28 (18) |
C16—C11—C12—C13 | −0.2 (3) | C25—C26—C27—C22 | −0.1 (3) |
C10—C11—C12—C13 | −178.87 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O1i | 0.97 | 2.48 | 3.432 (3) | 167 |
C7—H7···O2ii | 0.93 | 2.34 | 3.201 (3) | 153 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |