The chloroform solvate of uncarine C (pteropodine), (1′
S,3
R,4′a
S,5′a
S,10′a
S)-1,2,5′,5′a,7′,8′,10′,10′a-octahydro-1′-methyl-2-oxospiro[3
H-indole-3,6′(4′a
H)-[1
H]pyrano[3,4-
f]indolizine]-4′-carboxylic acid methyl ester, C
21H
24N
2O
4·CHCl
3, has an absolute configuration with the spiro C atom in the
R configuration. Its epimer at the spiro C atom, uncarine E (isopteropodine), (1′
S,3
S,4′a
S,5′a
S,10′a
S)-1,2,5′,5′a,7′,8′,10′,10′a-octahydro-1′-methyl-2-oxospiro[3
H-indole-3,6′(4′a
H)-[1
H]pyrano[3,4-
f]indolizine]-4′-carboxylic acid methyl ester, C
21H
24N
2O
4, has
Z′ = 3, with no solvent. Both form intermolecular hydrogen bonds involving only the oxindole, with N
O distances in the range 2.759 (4)–2.894 (5) Å.
Supporting information
CCDC references: 163941; 163942
Data collection: COLLECT (Nonius, 1999) for (I). Cell refinement: DENZO and Scalepak for (I); HKL SCALEPACK (Otwinowski & Minor, 1997) for (II). Data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997) for (I); HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (II). For both compounds, program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
(I) (1'
S,3
R,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8',10',10'a-octahydro-1'-
methyl-2-oxo-spiro[3
H-indole-3,6'(4'aH)-[1H]pyrano[3,4-
f]indolizine]-4'-carboxylic acid methyl ester, chloroform solvate
top
Crystal data top
C21H24N2O4·CHCl3 | F(000) = 508 |
Mr = 487.79 | Dx = 1.373 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3190 (5) Å | Cell parameters from 5602 reflections |
b = 7.7083 (7) Å | θ = 2.5–32.0° |
c = 16.8160 (14) Å | µ = 0.42 mm−1 |
β = 102.422 (4)° | T = 120 K |
V = 1179.63 (16) Å3 | Needle fragment, colorless |
Z = 2 | 0.32 × 0.12 × 0.08 mm |
Data collection top
KappaCCD (with Oxford Cryostream) diffractometer | 5101 independent reflections |
Radiation source: fine-focus sealed tube | 3176 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans with κ offsets | θmax = 32.0°, θmin = 2.7° |
Absorption correction: multi-scan (HKL Scalepack; Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.88, Tmax = 0.97 | k = −11→11 |
5602 measured reflections | l = −24→25 |
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)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0998P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
5101 reflections | Δρmax = 1.16 e Å−3 |
296 parameters | Δρmin = −0.65 e Å−3 |
1 restraint | Absolute structure: 740 Friedel pairs (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.09 (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 | Occ. (<1) |
Cl1 | 0.26597 (12) | 0.71119 (18) | 0.81031 (6) | 0.0586 (3) | |
Cl2 | 0.33839 (16) | 0.6657 (5) | 0.98325 (9) | 0.1295 (12) | |
Cl3 | 0.2804 (2) | 1.0009 (3) | 0.91474 (17) | 0.1112 (12) | 0.808 (5) |
Cl3A | 0.3465 (8) | 0.471 (2) | 0.9202 (8) | 0.133 (6) | 0.192 (5) |
O1 | 0.5371 (2) | 0.3817 (3) | 0.53112 (14) | 0.0316 (5) | |
O2 | 0.9536 (2) | 0.2756 (4) | 0.78596 (16) | 0.0363 (6) | |
O3 | 0.6795 (2) | 0.7135 (3) | 0.88630 (16) | 0.0375 (6) | |
O4 | 0.9254 (2) | 0.7009 (4) | 0.91649 (16) | 0.0387 (6) | |
N1 | 0.3517 (3) | 0.5782 (4) | 0.51841 (17) | 0.0285 (6) | |
H1 | 0.3784 | 0.6463 | 0.4822 | 0.034* | |
N2 | 0.4971 (3) | 0.1412 (3) | 0.68519 (16) | 0.0250 (5) | |
C2 | 0.4241 (3) | 0.4336 (4) | 0.54841 (19) | 0.0248 (6) | |
C3 | 0.4388 (3) | 0.3164 (4) | 0.69250 (19) | 0.0229 (6) | |
H3 | 0.3748 | 0.3117 | 0.7332 | 0.027* | |
C5 | 0.3695 (4) | 0.0399 (4) | 0.6464 (2) | 0.0318 (7) | |
H5A | 0.3067 | 0.0128 | 0.6854 | 0.038* | |
H5B | 0.3994 | −0.0698 | 0.6240 | 0.038* | |
C6 | 0.2903 (3) | 0.1582 (4) | 0.5790 (2) | 0.0274 (6) | |
H6A | 0.1826 | 0.1452 | 0.5715 | 0.033* | |
H6B | 0.3188 | 0.1308 | 0.5270 | 0.033* | |
C7 | 0.3390 (3) | 0.3469 (4) | 0.6075 (2) | 0.0241 (6) | |
C8 | 0.2158 (3) | 0.4741 (4) | 0.60547 (18) | 0.0247 (6) | |
C9 | 0.1011 (3) | 0.4739 (5) | 0.6468 (2) | 0.0289 (7) | |
H9 | 0.0920 | 0.3838 | 0.6840 | 0.035* | |
C10 | 0.0003 (3) | 0.6101 (5) | 0.6321 (2) | 0.0339 (8) | |
H10 | −0.0790 | 0.6120 | 0.6594 | 0.041* | |
C11 | 0.0133 (4) | 0.7424 (5) | 0.5784 (2) | 0.0342 (8) | |
H11 | −0.0568 | 0.8338 | 0.5697 | 0.041* | |
C12 | 0.1271 (4) | 0.7436 (5) | 0.5372 (2) | 0.0343 (8) | |
H12 | 0.1364 | 0.8337 | 0.5001 | 0.041* | |
C13 | 0.2268 (3) | 0.6078 (4) | 0.55232 (19) | 0.0267 (7) | |
C14 | 0.5626 (3) | 0.4445 (4) | 0.72333 (19) | 0.0246 (6) | |
H14A | 0.5209 | 0.5588 | 0.7328 | 0.030* | |
H14B | 0.6227 | 0.4593 | 0.6819 | 0.030* | |
C15 | 0.6600 (3) | 0.3771 (4) | 0.80332 (19) | 0.0247 (6) | |
H15 | 0.6008 | 0.3824 | 0.8463 | 0.030* | |
C16 | 0.7988 (3) | 0.4827 (5) | 0.83303 (19) | 0.0270 (6) | |
C17 | 0.9287 (4) | 0.4235 (5) | 0.8235 (2) | 0.0315 (7) | |
H17 | 1.0122 | 0.4928 | 0.8453 | 0.038* | |
C18 | 0.8783 (4) | −0.0020 (6) | 0.7328 (3) | 0.0453 (9) | |
H18A | 0.9582 | 0.0045 | 0.7034 | 0.068* | |
H18B | 0.7975 | −0.0712 | 0.7012 | 0.068* | |
H18C | 0.9143 | −0.0565 | 0.7860 | 0.068* | |
C19 | 0.8232 (3) | 0.1808 (5) | 0.7449 (2) | 0.0318 (7) | |
H19 | 0.7830 | 0.2349 | 0.6906 | 0.038* | |
C20 | 0.7074 (3) | 0.1876 (4) | 0.79660 (19) | 0.0268 (6) | |
H20 | 0.7537 | 0.1457 | 0.8525 | 0.032* | |
C21 | 0.5735 (3) | 0.0743 (4) | 0.7637 (2) | 0.0308 (7) | |
H21A | 0.6050 | −0.0467 | 0.7577 | 0.037* | |
H21B | 0.5069 | 0.0750 | 0.8023 | 0.037* | |
C22 | 0.7925 (3) | 0.6420 (5) | 0.87954 (19) | 0.0290 (7) | |
C23 | 0.9286 (4) | 0.8482 (5) | 0.9697 (2) | 0.0440 (10) | |
H23A | 0.8845 | 0.9487 | 0.9378 | 0.066* | |
H23B | 1.0307 | 0.8748 | 0.9959 | 0.066* | |
H23C | 0.8730 | 0.8214 | 1.0114 | 0.066* | |
C24 | 0.3546 (6) | 0.7966 (10) | 0.9032 (4) | 0.0485 (14) | 0.808 (5) |
H24 | 0.4613 | 0.8106 | 0.9031 | 0.058* | 0.808 (5) |
C24A | 0.368 (3) | 0.686 (4) | 0.9064 (17) | 0.050 (6)* | 0.192 (5) |
H24A | 0.4729 | 0.7166 | 0.9096 | 0.060* | 0.192 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0614 (6) | 0.0729 (8) | 0.0417 (6) | −0.0212 (6) | 0.0116 (5) | −0.0068 (6) |
Cl2 | 0.0770 (9) | 0.254 (4) | 0.0579 (8) | −0.0058 (14) | 0.0141 (7) | 0.0474 (16) |
Cl3 | 0.1007 (14) | 0.0782 (14) | 0.184 (3) | −0.0315 (11) | 0.0951 (16) | −0.0691 (16) |
Cl3A | 0.046 (4) | 0.167 (12) | 0.185 (12) | 0.012 (5) | 0.023 (5) | 0.111 (11) |
O1 | 0.0395 (12) | 0.0262 (12) | 0.0316 (13) | −0.0002 (10) | 0.0130 (10) | −0.0017 (11) |
O2 | 0.0310 (11) | 0.0350 (13) | 0.0451 (15) | 0.0011 (10) | 0.0133 (10) | −0.0075 (13) |
O3 | 0.0355 (12) | 0.0324 (13) | 0.0435 (14) | 0.0060 (11) | 0.0063 (10) | −0.0056 (13) |
O4 | 0.0337 (11) | 0.0357 (14) | 0.0427 (14) | −0.0017 (11) | −0.0004 (10) | −0.0109 (13) |
N1 | 0.0388 (13) | 0.0201 (12) | 0.0277 (14) | −0.0031 (11) | 0.0094 (11) | 0.0039 (12) |
N2 | 0.0309 (12) | 0.0161 (11) | 0.0271 (14) | −0.0006 (10) | 0.0042 (10) | 0.0033 (11) |
C2 | 0.0324 (15) | 0.0199 (13) | 0.0222 (15) | −0.0042 (12) | 0.0056 (12) | −0.0015 (13) |
C3 | 0.0305 (14) | 0.0169 (13) | 0.0220 (15) | −0.0007 (12) | 0.0071 (12) | 0.0013 (12) |
C5 | 0.0374 (16) | 0.0201 (15) | 0.0348 (18) | −0.0040 (13) | 0.0009 (14) | 0.0031 (14) |
C6 | 0.0330 (14) | 0.0208 (14) | 0.0265 (16) | −0.0014 (12) | 0.0023 (12) | −0.0047 (14) |
C7 | 0.0283 (14) | 0.0210 (14) | 0.0225 (15) | 0.0022 (12) | 0.0042 (12) | −0.0008 (13) |
C8 | 0.0259 (13) | 0.0221 (14) | 0.0238 (15) | 0.0035 (12) | 0.0007 (11) | −0.0009 (14) |
C9 | 0.0309 (14) | 0.0265 (15) | 0.0268 (16) | −0.0010 (13) | 0.0009 (12) | −0.0032 (15) |
C10 | 0.0284 (14) | 0.039 (2) | 0.0310 (17) | 0.0109 (14) | −0.0013 (13) | −0.0084 (16) |
C11 | 0.0338 (16) | 0.0282 (16) | 0.0354 (18) | 0.0081 (14) | −0.0042 (14) | −0.0067 (16) |
C12 | 0.0406 (17) | 0.0237 (15) | 0.0320 (18) | 0.0014 (14) | −0.0065 (14) | 0.0014 (15) |
C13 | 0.0322 (15) | 0.0200 (14) | 0.0245 (16) | −0.0026 (12) | −0.0015 (12) | −0.0028 (13) |
C14 | 0.0287 (14) | 0.0193 (14) | 0.0259 (15) | 0.0005 (12) | 0.0056 (12) | 0.0018 (13) |
C15 | 0.0266 (14) | 0.0252 (14) | 0.0223 (15) | 0.0014 (12) | 0.0051 (11) | 0.0023 (14) |
C16 | 0.0252 (13) | 0.0299 (16) | 0.0253 (15) | 0.0009 (13) | 0.0040 (11) | 0.0010 (15) |
C17 | 0.0314 (15) | 0.0324 (17) | 0.0311 (18) | −0.0005 (14) | 0.0077 (13) | −0.0029 (16) |
C18 | 0.0441 (19) | 0.0338 (18) | 0.060 (3) | 0.0051 (17) | 0.0157 (18) | −0.008 (2) |
C19 | 0.0345 (16) | 0.0277 (16) | 0.0340 (18) | 0.0028 (14) | 0.0095 (13) | −0.0036 (15) |
C20 | 0.0286 (14) | 0.0240 (14) | 0.0267 (16) | 0.0045 (12) | 0.0039 (12) | 0.0033 (14) |
C21 | 0.0362 (16) | 0.0230 (14) | 0.0320 (17) | −0.0020 (13) | 0.0045 (14) | 0.0069 (15) |
C22 | 0.0317 (15) | 0.0277 (15) | 0.0249 (15) | −0.0011 (14) | 0.0002 (12) | 0.0014 (15) |
C23 | 0.051 (2) | 0.038 (2) | 0.038 (2) | −0.0014 (17) | −0.0029 (17) | −0.0082 (19) |
C24 | 0.042 (3) | 0.065 (4) | 0.043 (3) | −0.015 (3) | 0.017 (2) | −0.015 (3) |
Geometric parameters (Å, º) top
Cl1—C24A | 1.70 (3) | C9—H9 | 0.9500 |
Cl1—C24 | 1.733 (6) | C10—C11 | 1.384 (5) |
Cl2—C24A | 1.39 (3) | C10—H10 | 0.9500 |
Cl2—C24 | 1.715 (7) | C11—C12 | 1.386 (5) |
Cl3—C24 | 1.748 (8) | C11—H11 | 0.9500 |
Cl3A—C24A | 1.69 (3) | C12—C13 | 1.386 (5) |
O1—C2 | 1.218 (4) | C12—H12 | 0.9500 |
O2—C17 | 1.347 (4) | C14—C15 | 1.542 (4) |
O2—C19 | 1.458 (4) | C14—H14A | 0.9900 |
O3—C22 | 1.215 (4) | C14—H14B | 0.9900 |
O4—C22 | 1.340 (4) | C15—C16 | 1.519 (4) |
O4—C23 | 1.442 (5) | C15—C20 | 1.537 (5) |
N1—C2 | 1.344 (4) | C15—H15 | 1.0000 |
N1—C13 | 1.420 (4) | C16—C17 | 1.336 (4) |
N1—H1 | 0.8800 | C16—C22 | 1.464 (5) |
N2—C21 | 1.454 (4) | C17—H17 | 0.9500 |
N2—C5 | 1.454 (4) | C18—C19 | 1.528 (5) |
N2—C3 | 1.470 (4) | C18—H18A | 0.9800 |
C2—C7 | 1.549 (5) | C18—H18B | 0.9800 |
C3—C14 | 1.523 (4) | C18—H18C | 0.9800 |
C3—C7 | 1.547 (4) | C19—C20 | 1.526 (4) |
C3—H3 | 1.0000 | C19—H19 | 1.0000 |
C5—C6 | 1.517 (5) | C20—C21 | 1.525 (5) |
C5—H5A | 0.9900 | C20—H20 | 1.0000 |
C5—H5B | 0.9900 | C21—H21A | 0.9900 |
C6—C7 | 1.568 (4) | C21—H21B | 0.9900 |
C6—H6A | 0.9900 | C23—H23A | 0.9800 |
C6—H6B | 0.9900 | C23—H23B | 0.9800 |
C7—C8 | 1.504 (4) | C23—H23C | 0.9800 |
C8—C13 | 1.382 (5) | C24—H24 | 1.0000 |
C8—C9 | 1.395 (4) | C24A—H24A | 1.0000 |
C9—C10 | 1.395 (5) | | |
| | | |
C17—O2—C19 | 115.9 (2) | H14A—C14—H14B | 108.2 |
C22—O4—C23 | 116.7 (3) | C16—C15—C20 | 107.2 (2) |
C2—N1—C13 | 111.8 (3) | C16—C15—C14 | 114.0 (3) |
C2—N1—H1 | 124.1 | C20—C15—C14 | 112.3 (3) |
C13—N1—H1 | 124.1 | C16—C15—H15 | 107.7 |
C21—N2—C5 | 114.2 (3) | C20—C15—H15 | 107.7 |
C21—N2—C3 | 111.6 (3) | C14—C15—H15 | 107.7 |
C5—N2—C3 | 104.4 (2) | C17—C16—C22 | 119.5 (3) |
O1—C2—N1 | 125.0 (3) | C17—C16—C15 | 120.5 (3) |
O1—C2—C7 | 126.8 (3) | C22—C16—C15 | 119.7 (3) |
N1—C2—C7 | 108.2 (3) | C16—C17—O2 | 126.7 (3) |
N2—C3—C14 | 110.9 (2) | C16—C17—H17 | 116.7 |
N2—C3—C7 | 102.8 (2) | O2—C17—H17 | 116.7 |
C14—C3—C7 | 118.5 (3) | C19—C18—H18A | 109.5 |
N2—C3—H3 | 108.0 | C19—C18—H18B | 109.5 |
C14—C3—H3 | 108.0 | H18A—C18—H18B | 109.5 |
C7—C3—H3 | 108.0 | C19—C18—H18C | 109.5 |
N2—C5—C6 | 103.4 (3) | H18A—C18—H18C | 109.5 |
N2—C5—H5A | 111.1 | H18B—C18—H18C | 109.5 |
C6—C5—H5A | 111.1 | O2—C19—C20 | 109.4 (3) |
N2—C5—H5B | 111.1 | O2—C19—C18 | 104.8 (3) |
C6—C5—H5B | 111.1 | C20—C19—C18 | 114.0 (3) |
H5A—C5—H5B | 109.1 | O2—C19—H19 | 109.5 |
C5—C6—C7 | 105.5 (2) | C20—C19—H19 | 109.5 |
C5—C6—H6A | 110.6 | C18—C19—H19 | 109.5 |
C7—C6—H6A | 110.6 | C21—C20—C19 | 113.4 (3) |
C5—C6—H6B | 110.6 | C21—C20—C15 | 110.2 (2) |
C7—C6—H6B | 110.6 | C19—C20—C15 | 108.9 (3) |
H6A—C6—H6B | 108.8 | C21—C20—H20 | 108.1 |
C8—C7—C3 | 115.1 (3) | C19—C20—H20 | 108.1 |
C8—C7—C2 | 101.4 (3) | C15—C20—H20 | 108.1 |
C3—C7—C2 | 111.7 (2) | N2—C21—C20 | 109.2 (3) |
C8—C7—C6 | 115.4 (3) | N2—C21—H21A | 109.8 |
C3—C7—C6 | 102.6 (2) | C20—C21—H21A | 109.8 |
C2—C7—C6 | 111.0 (3) | N2—C21—H21B | 109.8 |
C13—C8—C9 | 119.6 (3) | C20—C21—H21B | 109.8 |
C13—C8—C7 | 109.8 (3) | H21A—C21—H21B | 108.3 |
C9—C8—C7 | 130.6 (3) | O3—C22—O4 | 122.4 (3) |
C10—C9—C8 | 118.0 (3) | O3—C22—C16 | 124.5 (3) |
C10—C9—H9 | 121.0 | O4—C22—C16 | 113.1 (3) |
C8—C9—H9 | 121.0 | O4—C23—H23A | 109.5 |
C11—C10—C9 | 121.4 (3) | O4—C23—H23B | 109.5 |
C11—C10—H10 | 119.3 | H23A—C23—H23B | 109.5 |
C9—C10—H10 | 119.3 | O4—C23—H23C | 109.5 |
C10—C11—C12 | 121.0 (3) | H23A—C23—H23C | 109.5 |
C10—C11—H11 | 119.5 | H23B—C23—H23C | 109.5 |
C12—C11—H11 | 119.5 | Cl2—C24—Cl1 | 112.2 (4) |
C13—C12—C11 | 117.2 (3) | Cl2—C24—Cl3 | 109.9 (3) |
C13—C12—H12 | 121.4 | Cl1—C24—Cl3 | 108.6 (4) |
C11—C12—H12 | 121.4 | Cl2—C24—H24 | 108.7 |
C8—C13—C12 | 122.8 (3) | Cl1—C24—H24 | 108.7 |
C8—C13—N1 | 108.7 (3) | Cl3—C24—H24 | 108.7 |
C12—C13—N1 | 128.5 (3) | Cl2—C24A—Cl3A | 73.0 (15) |
C3—C14—C15 | 109.9 (3) | Cl2—C24A—Cl1 | 136.0 (17) |
C3—C14—H14A | 109.7 | Cl3A—C24A—Cl1 | 100.7 (16) |
C15—C14—H14A | 109.7 | Cl2—C24A—H24A | 111.3 |
C3—C14—H14B | 109.7 | Cl3A—C24A—H24A | 111.3 |
C15—C14—H14B | 109.7 | Cl1—C24A—H24A | 111.3 |
| | | |
C13—N1—C2—O1 | −177.8 (3) | C9—C8—C13—N1 | 179.9 (3) |
C13—N1—C2—C7 | 2.3 (3) | C7—C8—C13—N1 | −0.3 (3) |
C21—N2—C3—C14 | 62.7 (3) | C11—C12—C13—C8 | 0.4 (5) |
C5—N2—C3—C14 | −173.4 (3) | C11—C12—C13—N1 | 179.9 (3) |
C21—N2—C3—C7 | −169.6 (2) | C2—N1—C13—C8 | −1.4 (3) |
C5—N2—C3—C7 | −45.8 (3) | C2—N1—C13—C12 | 179.1 (3) |
C21—N2—C5—C6 | 166.2 (3) | N2—C3—C14—C15 | −54.0 (3) |
C3—N2—C5—C6 | 44.1 (3) | C7—C3—C14—C15 | −172.6 (3) |
N2—C5—C6—C7 | −24.6 (3) | C3—C14—C15—C16 | 172.0 (3) |
N2—C3—C7—C8 | 154.4 (3) | C3—C14—C15—C20 | 49.8 (3) |
C14—C3—C7—C8 | −82.9 (3) | C20—C15—C16—C17 | 21.6 (4) |
N2—C3—C7—C2 | −90.7 (3) | C14—C15—C16—C17 | −103.4 (4) |
C14—C3—C7—C2 | 32.0 (4) | C20—C15—C16—C22 | −152.4 (3) |
N2—C3—C7—C6 | 28.3 (3) | C14—C15—C16—C22 | 82.6 (4) |
C14—C3—C7—C6 | 151.0 (3) | C22—C16—C17—O2 | 176.6 (3) |
O1—C2—C7—C8 | 177.9 (3) | C15—C16—C17—O2 | 2.6 (6) |
N1—C2—C7—C8 | −2.3 (3) | C19—O2—C17—C16 | 6.6 (5) |
O1—C2—C7—C3 | 54.8 (4) | C17—O2—C19—C20 | −39.5 (4) |
N1—C2—C7—C3 | −125.4 (3) | C17—O2—C19—C18 | −162.1 (3) |
O1—C2—C7—C6 | −59.0 (4) | O2—C19—C20—C21 | −173.2 (3) |
N1—C2—C7—C6 | 120.8 (3) | C18—C19—C20—C21 | −56.3 (4) |
C5—C6—C7—C8 | −128.3 (3) | O2—C19—C20—C15 | 63.7 (3) |
C5—C6—C7—C3 | −2.4 (3) | C18—C19—C20—C15 | −179.4 (3) |
C5—C6—C7—C2 | 117.0 (3) | C16—C15—C20—C21 | −177.8 (3) |
C3—C7—C8—C13 | 122.2 (3) | C14—C15—C20—C21 | −51.8 (3) |
C2—C7—C8—C13 | 1.5 (3) | C16—C15—C20—C19 | −52.8 (3) |
C6—C7—C8—C13 | −118.6 (3) | C14—C15—C20—C19 | 73.2 (3) |
C3—C7—C8—C9 | −57.9 (4) | C5—N2—C21—C20 | 178.1 (3) |
C2—C7—C8—C9 | −178.7 (3) | C3—N2—C21—C20 | −63.7 (3) |
C6—C7—C8—C9 | 61.3 (4) | C19—C20—C21—N2 | −64.9 (3) |
C13—C8—C9—C10 | 0.5 (4) | C15—C20—C21—N2 | 57.5 (3) |
C7—C8—C9—C10 | −179.3 (3) | C23—O4—C22—O3 | 4.0 (5) |
C8—C9—C10—C11 | −0.4 (5) | C23—O4—C22—C16 | −174.5 (3) |
C9—C10—C11—C12 | 0.3 (5) | C17—C16—C22—O3 | 174.0 (4) |
C10—C11—C12—C13 | −0.3 (5) | C15—C16—C22—O3 | −12.0 (5) |
C9—C8—C13—C12 | −0.6 (4) | C17—C16—C22—O4 | −7.6 (5) |
C7—C8—C13—C12 | 179.3 (3) | C15—C16—C22—O4 | 166.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 2.01 | 2.759 (4) | 142 |
C9—H9···O2ii | 0.95 | 2.50 | 3.330 (4) | 146 |
C24—H24···O3 | 1.00 | 2.24 | 3.167 (6) | 153 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y, z. |
(II) (1'S,3
S,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8', 10',10'a-octahydro
-1'-methyl-2-oxo-spiro[3
H-indole-3,6'(4'aH)-[1H]pyrano[3,4-
f]
indolizine]-4'-carboxylic acid methyl ester
top
Crystal data top
C21H24N2O4 | The unit-cell dimensions at 296K were measured on an Enraf-Nonius
CAD4 diffractometer using CuKα radiation (λ=1.54184 Å), using 25
reflections in the theta range 15.6-19.6°. |
Mr = 368.42 | Dx = 1.298 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9943 (8) Å | Cell parameters from 6595 reflections |
b = 21.062 (3) Å | θ = 2.5–25.0° |
c = 12.3039 (15) Å | µ = 0.09 mm−1 |
β = 96.860 (6)° | T = 120 K |
V = 2828.7 (5) Å3 | Needle, colorless |
Z = 6 | 0.58 × 0.07 × 0.05 mm |
F(000) = 1176 | |
Data collection top
KappaCCD (with Oxford Cryostream) diffractometer | 4478 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 25.1°, θmin = 2.5° |
ω scans with κ offsets | h = −13→13 |
8293 measured reflections | k = −23→25 |
8293 independent reflections | l = −14→14 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0282P)2] where P = (Fo2 + 2Fc2)/3 |
8293 reflections | (Δ/σ)max = 0.001 |
736 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.25 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. |
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 | |
O1A | 0.9823 (3) | 0.24244 (16) | 0.4239 (3) | 0.0312 (9) | |
O2A | 0.5102 (3) | 0.40584 (16) | 0.7357 (3) | 0.0351 (9) | |
O3A | 0.6383 (3) | 0.44231 (17) | 0.3848 (3) | 0.0330 (9) | |
O4A | 0.5253 (3) | 0.51349 (15) | 0.4653 (3) | 0.0325 (9) | |
N1A | 1.1035 (3) | 0.30046 (19) | 0.5535 (3) | 0.0289 (11) | |
H1NA | 1.1601 | 0.3126 | 0.5130 | 0.035* | |
N2A | 0.7344 (3) | 0.23825 (18) | 0.6632 (3) | 0.0246 (10) | |
C2A | 1.0062 (4) | 0.2633 (2) | 0.5175 (5) | 0.0261 (13) | |
C3A | 0.7953 (4) | 0.2729 (2) | 0.5821 (4) | 0.0222 (12) | |
H3A | 0.7658 | 0.2555 | 0.5080 | 0.027* | |
C5A | 0.7790 (4) | 0.1731 (2) | 0.6534 (4) | 0.0324 (13) | |
H5A1 | 0.7341 | 0.1514 | 0.5894 | 0.039* | |
H5A2 | 0.7697 | 0.1483 | 0.7203 | 0.039* | |
C6A | 0.9155 (4) | 0.1816 (2) | 0.6385 (4) | 0.0283 (13) | |
H6A1 | 0.9374 | 0.1547 | 0.5777 | 0.034* | |
H6A2 | 0.9684 | 0.1698 | 0.7063 | 0.034* | |
C7A | 0.9309 (4) | 0.2528 (2) | 0.6121 (4) | 0.0235 (12) | |
C8A | 1.0015 (4) | 0.2898 (2) | 0.7027 (4) | 0.0255 (13) | |
C9A | 0.9833 (4) | 0.2982 (3) | 0.8110 (4) | 0.0344 (14) | |
H9A | 0.9140 | 0.2804 | 0.8391 | 0.041* | |
C10A | 1.0702 (5) | 0.3338 (3) | 0.8784 (5) | 0.0423 (15) | |
H10A | 1.0603 | 0.3398 | 0.9534 | 0.051* | |
C11A | 1.1700 (5) | 0.3602 (3) | 0.8367 (5) | 0.0380 (15) | |
H11A | 1.2268 | 0.3846 | 0.8837 | 0.046* | |
C12A | 1.1899 (4) | 0.3521 (2) | 0.7277 (4) | 0.0310 (13) | |
H12A | 1.2591 | 0.3695 | 0.6991 | 0.037* | |
C13A | 1.1020 (4) | 0.3171 (2) | 0.6641 (4) | 0.0269 (13) | |
C14A | 0.7642 (4) | 0.3432 (2) | 0.5827 (4) | 0.0248 (12) | |
H14A | 0.8059 | 0.3658 | 0.5271 | 0.030* | |
H14B | 0.7919 | 0.3617 | 0.6554 | 0.030* | |
C15A | 0.6228 (4) | 0.3502 (2) | 0.5561 (4) | 0.0237 (12) | |
H15A | 0.5986 | 0.3331 | 0.4808 | 0.028* | |
C16A | 0.5796 (4) | 0.4179 (2) | 0.5587 (4) | 0.0222 (12) | |
C17A | 0.5246 (4) | 0.4387 (3) | 0.6425 (4) | 0.0309 (13) | |
H17A | 0.4921 | 0.4805 | 0.6369 | 0.037* | |
C18A | 0.5073 (4) | 0.3097 (3) | 0.8343 (4) | 0.0376 (14) | |
H18A | 0.5031 | 0.3385 | 0.8964 | 0.056* | |
H18B | 0.5545 | 0.2718 | 0.8591 | 0.056* | |
H18C | 0.4243 | 0.2972 | 0.8040 | 0.056* | |
C19A | 0.5695 (4) | 0.3433 (2) | 0.7467 (4) | 0.0297 (13) | |
H19A | 0.6583 | 0.3490 | 0.7736 | 0.036* | |
C20A | 0.5577 (4) | 0.3109 (2) | 0.6362 (4) | 0.0224 (12) | |
H20A | 0.4686 | 0.3106 | 0.6077 | 0.027* | |
C21A | 0.6009 (4) | 0.2425 (2) | 0.6384 (4) | 0.0268 (13) | |
H21A | 0.5619 | 0.2188 | 0.6946 | 0.032* | |
H21B | 0.5752 | 0.2225 | 0.5665 | 0.032* | |
C22A | 0.5871 (4) | 0.4571 (2) | 0.4614 (5) | 0.0274 (13) | |
C23A | 0.5237 (4) | 0.5518 (2) | 0.3683 (4) | 0.0346 (14) | |
H23A | 0.6073 | 0.5561 | 0.3490 | 0.052* | |
H23B | 0.4909 | 0.5939 | 0.3819 | 0.052* | |
H23C | 0.4719 | 0.5315 | 0.3078 | 0.052* | |
O1B | 0.6194 (3) | 0.29109 (16) | 0.2775 (3) | 0.0310 (9) | |
O2B | 0.1452 (3) | 0.03740 (17) | 0.3765 (3) | 0.0396 (10) | |
O3B | 0.3279 (3) | 0.20947 (17) | 0.5859 (3) | 0.0351 (9) | |
O4B | 0.2100 (3) | 0.13731 (16) | 0.6582 (3) | 0.0352 (9) | |
N1B | 0.7486 (3) | 0.20499 (19) | 0.3081 (3) | 0.0274 (10) | |
H1NB | 0.8133 | 0.2252 | 0.3401 | 0.033* | |
N2B | 0.3560 (3) | 0.1505 (2) | 0.1553 (3) | 0.0306 (11) | |
C2B | 0.6403 (4) | 0.2338 (3) | 0.2699 (4) | 0.0279 (13) | |
C3B | 0.4278 (4) | 0.1855 (2) | 0.2464 (4) | 0.0273 (13) | |
H3B | 0.3997 | 0.2307 | 0.2440 | 0.033* | |
C5B | 0.3952 (4) | 0.1781 (3) | 0.0558 (4) | 0.0427 (15) | |
H5B1 | 0.3434 | 0.2151 | 0.0312 | 0.051* | |
H5B2 | 0.3895 | 0.1463 | −0.0039 | 0.051* | |
C6B | 0.5286 (4) | 0.1987 (3) | 0.0873 (4) | 0.0315 (13) | |
H6B1 | 0.5385 | 0.2446 | 0.0739 | 0.038* | |
H6B2 | 0.5842 | 0.1747 | 0.0447 | 0.038* | |
C7B | 0.5563 (4) | 0.1833 (2) | 0.2118 (4) | 0.0240 (12) | |
C8B | 0.6292 (4) | 0.1231 (2) | 0.2350 (4) | 0.0230 (12) | |
C9B | 0.6040 (4) | 0.0615 (2) | 0.2078 (4) | 0.0280 (13) | |
H9B | 0.5269 | 0.0500 | 0.1696 | 0.034* | |
C10B | 0.6934 (4) | 0.0156 (2) | 0.2369 (4) | 0.0317 (13) | |
H10B | 0.6764 | −0.0277 | 0.2191 | 0.038* | |
C11B | 0.8061 (5) | 0.0321 (2) | 0.2913 (4) | 0.0328 (14) | |
H11B | 0.8658 | 0.0001 | 0.3099 | 0.039* | |
C12B | 0.8337 (4) | 0.0952 (2) | 0.3195 (4) | 0.0307 (14) | |
H12B | 0.9109 | 0.1070 | 0.3573 | 0.037* | |
C13B | 0.7437 (4) | 0.1395 (2) | 0.2899 (4) | 0.0248 (12) | |
C14B | 0.4041 (4) | 0.1573 (2) | 0.3546 (4) | 0.0272 (12) | |
H14C | 0.4509 | 0.1810 | 0.4154 | 0.033* | |
H14D | 0.4317 | 0.1125 | 0.3589 | 0.033* | |
C15B | 0.2650 (4) | 0.1607 (2) | 0.3658 (4) | 0.0281 (13) | |
H15B | 0.2414 | 0.2066 | 0.3674 | 0.034* | |
C16B | 0.2319 (4) | 0.1300 (2) | 0.4691 (4) | 0.0283 (13) | |
C17B | 0.1742 (4) | 0.0741 (3) | 0.4652 (4) | 0.0325 (14) | |
H17B | 0.1513 | 0.0585 | 0.5323 | 0.039* | |
C18B | 0.1217 (5) | 0.0219 (3) | 0.1860 (5) | 0.0561 (18) | |
H18D | 0.1164 | −0.0227 | 0.2077 | 0.084* | |
H18E | 0.1621 | 0.0247 | 0.1193 | 0.084* | |
H18F | 0.0391 | 0.0399 | 0.1720 | 0.084* | |
C19B | 0.1942 (4) | 0.0582 (2) | 0.2758 (4) | 0.0346 (14) | |
H19B | 0.2819 | 0.0448 | 0.2800 | 0.041* | |
C20B | 0.1883 (4) | 0.1298 (3) | 0.2678 (4) | 0.0322 (14) | |
H20B | 0.1011 | 0.1422 | 0.2717 | 0.039* | |
C21B | 0.2245 (4) | 0.1571 (3) | 0.1602 (4) | 0.0347 (14) | |
H21C | 0.1790 | 0.1345 | 0.0974 | 0.042* | |
H21D | 0.2016 | 0.2025 | 0.1545 | 0.042* | |
C22B | 0.2621 (4) | 0.1639 (3) | 0.5727 (4) | 0.0289 (13) | |
C23B | 0.2466 (4) | 0.1669 (3) | 0.7629 (4) | 0.0391 (15) | |
H23D | 0.3357 | 0.1637 | 0.7807 | 0.059* | |
H23E | 0.2064 | 0.1454 | 0.8196 | 0.059* | |
H23F | 0.2226 | 0.2117 | 0.7596 | 0.059* | |
O1C | 1.3072 (3) | 0.33869 (17) | 0.4440 (3) | 0.0348 (9) | |
O2C | 0.7472 (3) | 0.40391 (17) | 0.0221 (3) | 0.0347 (9) | |
O3C | 0.9602 (3) | 0.21591 (16) | 0.1487 (3) | 0.0381 (10) | |
O4C | 0.8220 (3) | 0.21659 (16) | −0.0024 (3) | 0.0370 (9) | |
N1C | 1.4011 (3) | 0.36389 (19) | 0.2925 (3) | 0.0278 (10) | |
H1NC | 1.4620 | 0.3366 | 0.3022 | 0.033* | |
N2C | 1.0237 (3) | 0.45901 (18) | 0.3033 (3) | 0.0270 (10) | |
C2C | 1.3138 (4) | 0.3703 (2) | 0.3616 (4) | 0.0281 (13) | |
C3C | 1.0923 (4) | 0.3994 (2) | 0.3013 (4) | 0.0225 (12) | |
H3C | 1.0780 | 0.3738 | 0.3672 | 0.027* | |
C5C | 1.0820 (4) | 0.4919 (3) | 0.3996 (4) | 0.0358 (14) | |
H5C1 | 1.0512 | 0.4757 | 0.4667 | 0.043* | |
H5C2 | 1.0662 | 0.5381 | 0.3938 | 0.043* | |
C6C | 1.2186 (4) | 0.4779 (2) | 0.4015 (4) | 0.0312 (14) | |
H6C1 | 1.2544 | 0.4642 | 0.4755 | 0.037* | |
H6C2 | 1.2629 | 0.5161 | 0.3805 | 0.037* | |
C7C | 1.2264 (4) | 0.4238 (2) | 0.3170 (4) | 0.0238 (12) | |
C8C | 1.2771 (4) | 0.4428 (2) | 0.2134 (4) | 0.0242 (12) | |
C9C | 1.2432 (4) | 0.4879 (2) | 0.1348 (4) | 0.0319 (13) | |
H9C | 1.1734 | 0.5138 | 0.1402 | 0.038* | |
C10C | 1.3102 (4) | 0.4956 (3) | 0.0483 (5) | 0.0367 (14) | |
H10C | 1.2859 | 0.5263 | −0.0066 | 0.044* | |
C11C | 1.4129 (4) | 0.4588 (3) | 0.0410 (4) | 0.0377 (14) | |
H11C | 1.4586 | 0.4650 | −0.0189 | 0.045* | |
C12C | 1.4511 (4) | 0.4129 (2) | 0.1188 (4) | 0.0283 (13) | |
H12C | 1.5215 | 0.3876 | 0.1134 | 0.034* | |
C13C | 1.3822 (4) | 0.4061 (2) | 0.2039 (4) | 0.0231 (12) | |
C14C | 1.0493 (4) | 0.3612 (2) | 0.2003 (4) | 0.0266 (13) | |
H14E | 1.0968 | 0.3213 | 0.2001 | 0.032* | |
H14F | 1.0620 | 0.3856 | 0.1339 | 0.032* | |
C15C | 0.9116 (4) | 0.3459 (2) | 0.1997 (4) | 0.0243 (12) | |
H15C | 0.9025 | 0.3174 | 0.2634 | 0.029* | |
C16C | 0.8578 (4) | 0.3127 (2) | 0.0979 (4) | 0.0234 (12) | |
C17C | 0.7784 (4) | 0.3419 (3) | 0.0219 (4) | 0.0323 (13) | |
H17C | 0.7412 | 0.3167 | −0.0369 | 0.039* | |
C18C | 0.7445 (5) | 0.5037 (2) | 0.1080 (5) | 0.0414 (15) | |
H18G | 0.7127 | 0.5162 | 0.0332 | 0.062* | |
H18H | 0.7975 | 0.5375 | 0.1420 | 0.062* | |
H18I | 0.6760 | 0.4969 | 0.1508 | 0.062* | |
C19C | 0.8171 (4) | 0.4433 (2) | 0.1050 (4) | 0.0320 (13) | |
H19C | 0.8988 | 0.4532 | 0.0811 | 0.038* | |
C20C | 0.8355 (4) | 0.4071 (2) | 0.2130 (4) | 0.0253 (12) | |
H20C | 0.7528 | 0.3934 | 0.2298 | 0.030* | |
C21C | 0.8925 (4) | 0.4462 (2) | 0.3096 (4) | 0.0271 (12) | |
H21E | 0.8481 | 0.4870 | 0.3114 | 0.032* | |
H21F | 0.8837 | 0.4231 | 0.3783 | 0.032* | |
C22C | 0.8863 (4) | 0.2453 (2) | 0.0870 (4) | 0.0279 (13) | |
C23C | 0.8493 (5) | 0.1506 (3) | −0.0161 (5) | 0.0567 (19) | |
H23G | 0.9328 | 0.1464 | −0.0356 | 0.085* | |
H23H | 0.7911 | 0.1326 | −0.0746 | 0.085* | |
H23I | 0.8428 | 0.1279 | 0.0524 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0217 (17) | 0.039 (2) | 0.032 (2) | 0.0032 (16) | 0.0035 (16) | −0.0040 (19) |
O2A | 0.039 (2) | 0.036 (2) | 0.032 (2) | 0.0118 (18) | 0.0106 (17) | 0.0059 (19) |
O3A | 0.0325 (19) | 0.036 (2) | 0.032 (2) | 0.0016 (17) | 0.0105 (18) | 0.001 (2) |
O4A | 0.0322 (19) | 0.026 (2) | 0.040 (2) | 0.0071 (17) | 0.0066 (17) | 0.0057 (19) |
N1A | 0.021 (2) | 0.032 (3) | 0.036 (3) | −0.008 (2) | 0.0076 (19) | 0.003 (2) |
N2A | 0.019 (2) | 0.027 (3) | 0.028 (3) | 0.0024 (19) | 0.0055 (18) | 0.005 (2) |
C2A | 0.021 (3) | 0.026 (3) | 0.030 (4) | 0.002 (2) | −0.001 (2) | 0.003 (3) |
C3A | 0.018 (2) | 0.024 (3) | 0.025 (3) | 0.002 (2) | 0.004 (2) | 0.002 (2) |
C5A | 0.027 (3) | 0.026 (3) | 0.044 (4) | −0.001 (2) | 0.004 (2) | 0.000 (3) |
C6A | 0.024 (2) | 0.023 (3) | 0.038 (3) | 0.007 (2) | 0.005 (2) | 0.004 (3) |
C7A | 0.014 (2) | 0.027 (3) | 0.029 (3) | 0.001 (2) | 0.002 (2) | −0.002 (3) |
C8A | 0.022 (3) | 0.024 (3) | 0.030 (3) | 0.001 (2) | 0.001 (2) | 0.007 (3) |
C9A | 0.031 (3) | 0.043 (4) | 0.029 (4) | 0.002 (3) | 0.003 (2) | 0.002 (3) |
C10A | 0.038 (3) | 0.056 (4) | 0.032 (4) | −0.005 (3) | 0.000 (3) | −0.002 (3) |
C11A | 0.033 (3) | 0.041 (4) | 0.039 (4) | −0.010 (3) | −0.001 (3) | −0.008 (3) |
C12A | 0.029 (3) | 0.030 (3) | 0.033 (4) | 0.003 (2) | 0.003 (3) | −0.003 (3) |
C13A | 0.029 (3) | 0.029 (3) | 0.023 (3) | −0.001 (2) | 0.002 (2) | 0.000 (3) |
C14A | 0.016 (2) | 0.028 (3) | 0.030 (3) | −0.002 (2) | 0.000 (2) | −0.003 (3) |
C15A | 0.015 (2) | 0.032 (3) | 0.024 (3) | −0.003 (2) | 0.003 (2) | −0.003 (3) |
C16A | 0.021 (3) | 0.023 (3) | 0.023 (3) | 0.001 (2) | 0.003 (2) | −0.004 (3) |
C17A | 0.028 (3) | 0.027 (3) | 0.037 (4) | 0.005 (2) | 0.002 (3) | 0.001 (3) |
C18A | 0.030 (3) | 0.055 (4) | 0.029 (3) | 0.005 (3) | 0.005 (2) | 0.002 (3) |
C19A | 0.025 (3) | 0.034 (3) | 0.031 (3) | 0.007 (2) | 0.004 (2) | 0.006 (3) |
C20A | 0.011 (2) | 0.031 (3) | 0.025 (3) | −0.003 (2) | 0.001 (2) | −0.002 (3) |
C21A | 0.014 (2) | 0.038 (3) | 0.029 (3) | −0.003 (2) | 0.006 (2) | 0.007 (3) |
C22A | 0.025 (3) | 0.024 (3) | 0.031 (4) | −0.003 (2) | −0.004 (3) | −0.006 (3) |
C23A | 0.034 (3) | 0.032 (3) | 0.038 (4) | −0.002 (3) | 0.001 (3) | 0.004 (3) |
O1B | 0.0295 (19) | 0.022 (2) | 0.043 (2) | −0.0027 (16) | 0.0102 (17) | −0.0004 (18) |
O2B | 0.035 (2) | 0.043 (2) | 0.041 (3) | −0.0125 (18) | 0.0052 (19) | −0.002 (2) |
O3B | 0.0296 (19) | 0.034 (2) | 0.042 (2) | −0.0048 (18) | 0.0025 (17) | 0.0013 (19) |
O4B | 0.0371 (19) | 0.040 (2) | 0.029 (2) | −0.0025 (17) | 0.0074 (18) | 0.0038 (19) |
N1B | 0.021 (2) | 0.025 (3) | 0.037 (3) | −0.0034 (19) | 0.0031 (19) | 0.000 (2) |
N2B | 0.018 (2) | 0.049 (3) | 0.024 (3) | −0.0038 (19) | 0.0018 (19) | 0.003 (2) |
C2B | 0.023 (3) | 0.034 (4) | 0.028 (3) | 0.003 (2) | 0.008 (2) | 0.003 (3) |
C3B | 0.023 (3) | 0.029 (3) | 0.030 (3) | 0.001 (2) | 0.004 (2) | −0.001 (3) |
C5B | 0.034 (3) | 0.064 (4) | 0.032 (4) | −0.008 (3) | 0.007 (3) | 0.008 (3) |
C6B | 0.022 (3) | 0.046 (4) | 0.027 (3) | 0.002 (2) | 0.005 (2) | 0.007 (3) |
C7B | 0.013 (2) | 0.029 (3) | 0.030 (3) | 0.000 (2) | 0.001 (2) | 0.001 (3) |
C8B | 0.024 (3) | 0.026 (3) | 0.020 (3) | −0.004 (2) | 0.009 (2) | −0.005 (2) |
C9B | 0.021 (3) | 0.039 (4) | 0.024 (3) | −0.005 (3) | 0.003 (2) | −0.008 (3) |
C10B | 0.031 (3) | 0.029 (3) | 0.037 (4) | 0.000 (3) | 0.013 (3) | −0.003 (3) |
C11B | 0.035 (3) | 0.032 (4) | 0.031 (3) | 0.007 (3) | 0.004 (3) | 0.006 (3) |
C12B | 0.023 (3) | 0.038 (4) | 0.031 (3) | −0.001 (3) | −0.002 (2) | 0.005 (3) |
C13B | 0.020 (3) | 0.027 (3) | 0.027 (3) | −0.002 (2) | 0.003 (2) | 0.000 (3) |
C14B | 0.022 (2) | 0.032 (3) | 0.028 (3) | 0.000 (2) | 0.004 (2) | −0.001 (3) |
C15B | 0.021 (2) | 0.033 (3) | 0.031 (3) | 0.003 (2) | 0.007 (2) | 0.008 (3) |
C16B | 0.020 (3) | 0.030 (3) | 0.035 (4) | −0.004 (2) | 0.005 (2) | 0.008 (3) |
C17B | 0.031 (3) | 0.042 (4) | 0.024 (3) | 0.005 (3) | 0.001 (3) | 0.002 (3) |
C18B | 0.058 (4) | 0.068 (5) | 0.043 (4) | −0.027 (4) | 0.007 (3) | −0.012 (4) |
C19B | 0.026 (3) | 0.042 (4) | 0.036 (4) | −0.010 (3) | 0.007 (3) | −0.003 (3) |
C20B | 0.020 (2) | 0.044 (4) | 0.032 (3) | −0.005 (3) | 0.001 (2) | 0.003 (3) |
C21B | 0.016 (2) | 0.057 (4) | 0.031 (3) | −0.001 (3) | 0.001 (2) | 0.003 (3) |
C22B | 0.022 (3) | 0.033 (4) | 0.032 (4) | 0.014 (3) | 0.006 (3) | 0.009 (3) |
C23B | 0.044 (3) | 0.042 (4) | 0.032 (4) | 0.009 (3) | 0.004 (3) | 0.001 (3) |
O1C | 0.0231 (18) | 0.043 (2) | 0.039 (2) | −0.0007 (17) | 0.0047 (17) | 0.011 (2) |
O2C | 0.0325 (19) | 0.036 (2) | 0.034 (2) | 0.0034 (18) | −0.0028 (17) | −0.0011 (19) |
O3C | 0.038 (2) | 0.030 (2) | 0.044 (3) | 0.0054 (18) | −0.0041 (18) | −0.0004 (19) |
O4C | 0.044 (2) | 0.030 (2) | 0.037 (2) | −0.0094 (18) | 0.0024 (18) | −0.0092 (18) |
N1C | 0.020 (2) | 0.028 (3) | 0.036 (3) | 0.0004 (19) | 0.005 (2) | 0.007 (2) |
N2C | 0.023 (2) | 0.026 (3) | 0.032 (3) | 0.0011 (19) | 0.0040 (19) | −0.009 (2) |
C2C | 0.023 (3) | 0.034 (3) | 0.026 (3) | −0.004 (2) | 0.000 (3) | 0.006 (3) |
C3C | 0.025 (3) | 0.023 (3) | 0.021 (3) | 0.003 (2) | 0.007 (2) | −0.001 (2) |
C5C | 0.028 (3) | 0.046 (4) | 0.035 (3) | −0.004 (3) | 0.008 (3) | −0.017 (3) |
C6C | 0.019 (3) | 0.040 (4) | 0.036 (4) | 0.001 (2) | 0.007 (2) | −0.014 (3) |
C7C | 0.018 (2) | 0.026 (3) | 0.028 (3) | −0.006 (2) | 0.005 (2) | −0.007 (3) |
C8C | 0.026 (3) | 0.018 (3) | 0.029 (3) | −0.006 (2) | 0.008 (2) | −0.006 (3) |
C9C | 0.026 (3) | 0.026 (3) | 0.044 (4) | −0.003 (2) | 0.005 (3) | 0.002 (3) |
C10C | 0.034 (3) | 0.035 (4) | 0.042 (4) | 0.007 (3) | 0.008 (3) | 0.010 (3) |
C11C | 0.035 (3) | 0.047 (4) | 0.032 (3) | 0.000 (3) | 0.010 (3) | −0.003 (3) |
C12C | 0.030 (3) | 0.021 (3) | 0.033 (3) | 0.005 (2) | 0.003 (3) | −0.002 (3) |
C13C | 0.019 (3) | 0.028 (3) | 0.023 (3) | −0.005 (2) | 0.001 (2) | −0.002 (3) |
C14C | 0.019 (2) | 0.028 (3) | 0.032 (3) | −0.004 (2) | 0.003 (2) | −0.004 (2) |
C15C | 0.022 (2) | 0.024 (3) | 0.027 (3) | 0.002 (2) | 0.003 (2) | −0.003 (2) |
C16C | 0.022 (3) | 0.022 (3) | 0.027 (3) | −0.002 (2) | 0.006 (2) | −0.002 (3) |
C17C | 0.031 (3) | 0.035 (3) | 0.031 (3) | −0.001 (3) | 0.002 (3) | −0.003 (3) |
C18C | 0.044 (3) | 0.026 (3) | 0.053 (4) | 0.010 (3) | 0.001 (3) | 0.002 (3) |
C19C | 0.028 (3) | 0.029 (3) | 0.039 (4) | −0.006 (3) | 0.004 (2) | 0.002 (3) |
C20C | 0.018 (2) | 0.031 (3) | 0.027 (3) | −0.004 (2) | 0.006 (2) | −0.001 (3) |
C21C | 0.020 (2) | 0.032 (3) | 0.030 (3) | −0.006 (2) | 0.005 (2) | −0.003 (3) |
C22C | 0.027 (3) | 0.031 (3) | 0.028 (3) | −0.007 (3) | 0.016 (3) | −0.008 (3) |
C23C | 0.060 (4) | 0.031 (4) | 0.078 (5) | −0.008 (3) | 0.003 (3) | −0.024 (3) |
Geometric parameters (Å, º) top
O1A—C2A | 1.231 (5) | C10B—H10B | 0.9500 |
O2A—C17A | 1.365 (6) | C11B—C12B | 1.398 (7) |
O2A—C19A | 1.470 (6) | C11B—H11B | 0.9500 |
O3A—C22A | 1.196 (6) | C12B—C13B | 1.376 (6) |
O4A—C22A | 1.372 (6) | C12B—H12B | 0.9500 |
O4A—C23A | 1.439 (6) | C14B—C15B | 1.554 (6) |
N1A—C2A | 1.356 (6) | C14B—H14C | 0.9900 |
N1A—C13A | 1.407 (6) | C14B—H14D | 0.9900 |
N1A—H1NA | 0.8800 | C15B—C16B | 1.510 (6) |
N2A—C3A | 1.461 (6) | C15B—C20B | 1.531 (6) |
N2A—C21A | 1.467 (5) | C15B—H15B | 1.0000 |
N2A—C5A | 1.466 (6) | C16B—C17B | 1.336 (7) |
C2A—C7A | 1.523 (7) | C16B—C22B | 1.463 (7) |
C3A—C14A | 1.519 (6) | C17B—H17B | 0.9500 |
C3A—C7A | 1.552 (6) | C18B—C19B | 1.493 (7) |
C3A—H3A | 1.0000 | C18B—H18D | 0.9800 |
C5A—C6A | 1.544 (6) | C18B—H18E | 0.9800 |
C5A—H5A1 | 0.9900 | C18B—H18F | 0.9800 |
C5A—H5A2 | 0.9900 | C19B—C20B | 1.511 (7) |
C6A—C7A | 1.548 (6) | C19B—H19B | 1.0000 |
C6A—H6A1 | 0.9900 | C20B—C21B | 1.539 (6) |
C6A—H6A2 | 0.9900 | C20B—H20B | 1.0000 |
C7A—C8A | 1.499 (6) | C21B—H21C | 0.9900 |
C8A—C13A | 1.378 (6) | C21B—H21D | 0.9900 |
C8A—C9A | 1.382 (6) | C23B—H23D | 0.9800 |
C9A—C10A | 1.405 (7) | C23B—H23E | 0.9800 |
C9A—H9A | 0.9500 | C23B—H23F | 0.9800 |
C10A—C11A | 1.382 (7) | O1C—C2C | 1.222 (6) |
C10A—H10A | 0.9500 | O2C—C17C | 1.349 (6) |
C11A—C12A | 1.394 (7) | O2C—C19C | 1.459 (5) |
C11A—H11A | 0.9500 | O3C—C22C | 1.213 (5) |
C12A—C13A | 1.382 (6) | O4C—C22C | 1.374 (5) |
C12A—H12A | 0.9500 | O4C—C23C | 1.436 (6) |
C14A—C15A | 1.557 (5) | N1C—C2C | 1.362 (6) |
C14A—H14A | 0.9900 | N1C—C13C | 1.402 (6) |
C14A—H14B | 0.9900 | N1C—H1NC | 0.8800 |
C15A—C16A | 1.507 (7) | N2C—C5C | 1.453 (6) |
C15A—C20A | 1.528 (6) | N2C—C3C | 1.467 (5) |
C15A—H15A | 1.0000 | N2C—C21C | 1.479 (5) |
C16A—C17A | 1.329 (6) | C2C—C7C | 1.539 (6) |
C16A—C22A | 1.464 (7) | C3C—C14C | 1.508 (6) |
C17A—H17A | 0.9500 | C3C—C7C | 1.552 (6) |
C18A—C19A | 1.517 (7) | C3C—H3C | 1.0000 |
C18A—H18A | 0.9800 | C5C—C6C | 1.528 (6) |
C18A—H18B | 0.9800 | C5C—H5C1 | 0.9900 |
C18A—H18C | 0.9800 | C5C—H5C2 | 0.9900 |
C19A—C20A | 1.513 (6) | C6C—C7C | 1.553 (6) |
C19A—H19A | 1.0000 | C6C—H6C1 | 0.9900 |
C20A—C21A | 1.516 (7) | C6C—H6C2 | 0.9900 |
C20A—H20A | 1.0000 | C7C—C8C | 1.504 (7) |
C21A—H21A | 0.9900 | C8C—C9C | 1.376 (6) |
C21A—H21B | 0.9900 | C8C—C13C | 1.407 (6) |
C23A—H23A | 0.9800 | C9C—C10C | 1.374 (7) |
C23A—H23B | 0.9800 | C9C—H9C | 0.9500 |
C23A—H23C | 0.9800 | C10C—C11C | 1.381 (7) |
O1B—C2B | 1.234 (6) | C10C—H10C | 0.9500 |
O2B—C17B | 1.344 (6) | C11C—C12C | 1.389 (7) |
O2B—C19B | 1.475 (6) | C11C—H11C | 0.9500 |
O3B—C22B | 1.201 (6) | C12C—C13C | 1.371 (6) |
O4B—C22B | 1.376 (6) | C12C—H12C | 0.9500 |
O4B—C23B | 1.445 (5) | C14C—C15C | 1.547 (6) |
N1B—C2B | 1.369 (6) | C14C—H14E | 0.9900 |
N1B—C13B | 1.398 (6) | C14C—H14F | 0.9900 |
N1B—H1NB | 0.8800 | C15C—C16C | 1.493 (6) |
N2B—C21B | 1.461 (5) | C15C—C20C | 1.556 (6) |
N2B—C5B | 1.466 (6) | C15C—H15C | 1.0000 |
N2B—C3B | 1.487 (6) | C16C—C17C | 1.349 (6) |
C2B—C7B | 1.528 (6) | C16C—C22C | 1.463 (7) |
C3B—C14B | 1.509 (6) | C17C—H17C | 0.9500 |
C3B—C7B | 1.524 (6) | C18C—C19C | 1.506 (7) |
C3B—H3B | 1.0000 | C18C—H18G | 0.9800 |
C5B—C6B | 1.535 (6) | C18C—H18H | 0.9800 |
C5B—H5B1 | 0.9900 | C18C—H18I | 0.9800 |
C5B—H5B2 | 0.9900 | C19C—C20C | 1.524 (6) |
C6B—C7B | 1.559 (6) | C19C—H19C | 1.0000 |
C6B—H6B1 | 0.9900 | C20C—C21C | 1.517 (6) |
C6B—H6B2 | 0.9900 | C20C—H20C | 1.0000 |
C7B—C8B | 1.509 (6) | C21C—H21E | 0.9900 |
C8B—C9B | 1.359 (6) | C21C—H21F | 0.9900 |
C8B—C13B | 1.399 (6) | C23C—H23G | 0.9800 |
C9B—C10B | 1.395 (6) | C23C—H23H | 0.9800 |
C9B—H9B | 0.9500 | C23C—H23I | 0.9800 |
C10B—C11B | 1.381 (7) | | |
| | | |
C17A—O2A—C19A | 115.9 (4) | N1B—C13B—C8B | 109.6 (4) |
C22A—O4A—C23A | 114.4 (4) | C3B—C14B—C15B | 109.6 (4) |
C2A—N1A—C13A | 111.1 (4) | C3B—C14B—H14C | 109.8 |
C2A—N1A—H1NA | 124.5 | C15B—C14B—H14C | 109.8 |
C13A—N1A—H1NA | 124.5 | C3B—C14B—H14D | 109.8 |
C3A—N2A—C21A | 110.9 (3) | C15B—C14B—H14D | 109.8 |
C3A—N2A—C5A | 103.1 (4) | H14C—C14B—H14D | 108.2 |
C21A—N2A—C5A | 112.1 (4) | C16B—C15B—C20B | 108.3 (4) |
O1A—C2A—N1A | 125.7 (5) | C16B—C15B—C14B | 113.1 (4) |
O1A—C2A—C7A | 126.0 (4) | C20B—C15B—C14B | 111.5 (4) |
N1A—C2A—C7A | 108.3 (4) | C16B—C15B—H15B | 107.9 |
N2A—C3A—C14A | 111.3 (4) | C20B—C15B—H15B | 107.9 |
N2A—C3A—C7A | 101.9 (3) | C14B—C15B—H15B | 107.9 |
C14A—C3A—C7A | 118.4 (4) | C17B—C16B—C22B | 121.3 (5) |
N2A—C3A—H3A | 108.3 | C17B—C16B—C15B | 120.6 (5) |
C14A—C3A—H3A | 108.3 | C22B—C16B—C15B | 118.1 (5) |
C7A—C3A—H3A | 108.3 | C16B—C17B—O2B | 127.0 (5) |
N2A—C5A—C6A | 103.9 (4) | C16B—C17B—H17B | 116.5 |
N2A—C5A—H5A1 | 111.0 | O2B—C17B—H17B | 116.5 |
C6A—C5A—H5A1 | 111.0 | C19B—C18B—H18D | 109.5 |
N2A—C5A—H5A2 | 111.0 | C19B—C18B—H18E | 109.5 |
C6A—C5A—H5A2 | 111.0 | H18D—C18B—H18E | 109.5 |
H5A1—C5A—H5A2 | 109.0 | C19B—C18B—H18F | 109.5 |
C5A—C6A—C7A | 105.6 (4) | H18D—C18B—H18F | 109.5 |
C5A—C6A—H6A1 | 110.6 | H18E—C18B—H18F | 109.5 |
C7A—C6A—H6A1 | 110.6 | O2B—C19B—C18B | 104.6 (4) |
C5A—C6A—H6A2 | 110.6 | O2B—C19B—C20B | 109.5 (4) |
C7A—C6A—H6A2 | 110.6 | C18B—C19B—C20B | 116.6 (5) |
H6A1—C6A—H6A2 | 108.8 | O2B—C19B—H19B | 108.6 |
C8A—C7A—C2A | 102.3 (4) | C18B—C19B—H19B | 108.6 |
C8A—C7A—C6A | 114.1 (4) | C20B—C19B—H19B | 108.6 |
C2A—C7A—C6A | 112.6 (4) | C19B—C20B—C15B | 111.0 (4) |
C8A—C7A—C3A | 115.6 (4) | C19B—C20B—C21B | 114.5 (4) |
C2A—C7A—C3A | 111.9 (4) | C15B—C20B—C21B | 110.1 (4) |
C6A—C7A—C3A | 100.9 (3) | C19B—C20B—H20B | 107.0 |
C13A—C8A—C9A | 119.5 (4) | C15B—C20B—H20B | 107.0 |
C13A—C8A—C7A | 109.0 (4) | C21B—C20B—H20B | 107.0 |
C9A—C8A—C7A | 131.4 (5) | N2B—C21B—C20B | 111.0 (4) |
C8A—C9A—C10A | 118.1 (5) | N2B—C21B—H21C | 109.4 |
C8A—C9A—H9A | 121.0 | C20B—C21B—H21C | 109.4 |
C10A—C9A—H9A | 121.0 | N2B—C21B—H21D | 109.4 |
C11A—C10A—C9A | 120.6 (5) | C20B—C21B—H21D | 109.4 |
C11A—C10A—H10A | 119.7 | H21C—C21B—H21D | 108.0 |
C9A—C10A—H10A | 119.7 | O3B—C22B—O4B | 121.4 (5) |
C10A—C11A—C12A | 122.0 (5) | O3B—C22B—C16B | 125.3 (5) |
C10A—C11A—H11A | 119.0 | O4B—C22B—C16B | 113.3 (5) |
C12A—C11A—H11A | 119.0 | O4B—C23B—H23D | 109.5 |
C13A—C12A—C11A | 115.5 (5) | O4B—C23B—H23E | 109.5 |
C13A—C12A—H12A | 122.3 | H23D—C23B—H23E | 109.5 |
C11A—C12A—H12A | 122.3 | O4B—C23B—H23F | 109.5 |
C8A—C13A—C12A | 124.2 (5) | H23D—C23B—H23F | 109.5 |
C8A—C13A—N1A | 109.4 (4) | H23E—C23B—H23F | 109.5 |
C12A—C13A—N1A | 126.3 (5) | C17C—O2C—C19C | 116.0 (4) |
C3A—C14A—C15A | 108.1 (4) | C22C—O4C—C23C | 115.2 (4) |
C3A—C14A—H14A | 110.1 | C2C—N1C—C13C | 111.9 (4) |
C15A—C14A—H14A | 110.1 | C2C—N1C—H1NC | 124.1 |
C3A—C14A—H14B | 110.1 | C13C—N1C—H1NC | 124.1 |
C15A—C14A—H14B | 110.1 | C5C—N2C—C3C | 104.2 (3) |
H14A—C14A—H14B | 108.4 | C5C—N2C—C21C | 112.5 (4) |
C16A—C15A—C20A | 109.0 (4) | C3C—N2C—C21C | 110.5 (4) |
C16A—C15A—C14A | 113.3 (4) | O1C—C2C—N1C | 125.5 (5) |
C20A—C15A—C14A | 110.3 (4) | O1C—C2C—C7C | 126.7 (5) |
C16A—C15A—H15A | 108.0 | N1C—C2C—C7C | 107.8 (4) |
C20A—C15A—H15A | 108.0 | N2C—C3C—C14C | 111.1 (4) |
C14A—C15A—H15A | 108.0 | N2C—C3C—C7C | 101.3 (4) |
C17A—C16A—C22A | 121.6 (5) | C14C—C3C—C7C | 118.6 (4) |
C17A—C16A—C15A | 120.1 (5) | N2C—C3C—H3C | 108.4 |
C22A—C16A—C15A | 117.9 (4) | C14C—C3C—H3C | 108.4 |
C16A—C17A—O2A | 126.4 (5) | C7C—C3C—H3C | 108.4 |
C16A—C17A—H17A | 116.8 | N2C—C5C—C6C | 104.9 (4) |
O2A—C17A—H17A | 116.8 | N2C—C5C—H5C1 | 110.8 |
C19A—C18A—H18A | 109.5 | C6C—C5C—H5C1 | 110.8 |
C19A—C18A—H18B | 109.5 | N2C—C5C—H5C2 | 110.8 |
H18A—C18A—H18B | 109.5 | C6C—C5C—H5C2 | 110.8 |
C19A—C18A—H18C | 109.5 | H5C1—C5C—H5C2 | 108.8 |
H18A—C18A—H18C | 109.5 | C5C—C6C—C7C | 105.3 (4) |
H18B—C18A—H18C | 109.5 | C5C—C6C—H6C1 | 110.7 |
O2A—C19A—C20A | 109.4 (4) | C7C—C6C—H6C1 | 110.7 |
O2A—C19A—C18A | 104.5 (4) | C5C—C6C—H6C2 | 110.7 |
C20A—C19A—C18A | 115.5 (4) | C7C—C6C—H6C2 | 110.7 |
O2A—C19A—H19A | 109.1 | H6C1—C6C—H6C2 | 108.8 |
C20A—C19A—H19A | 109.1 | C8C—C7C—C2C | 102.6 (4) |
C18A—C19A—H19A | 109.1 | C8C—C7C—C3C | 115.2 (4) |
C19A—C20A—C21A | 114.8 (4) | C2C—C7C—C3C | 110.2 (4) |
C19A—C20A—C15A | 109.8 (4) | C8C—C7C—C6C | 115.3 (4) |
C21A—C20A—C15A | 110.9 (4) | C2C—C7C—C6C | 112.4 (4) |
C19A—C20A—H20A | 107.0 | C3C—C7C—C6C | 101.4 (4) |
C21A—C20A—H20A | 107.0 | C9C—C8C—C13C | 118.5 (5) |
C15A—C20A—H20A | 107.0 | C9C—C8C—C7C | 133.1 (5) |
N2A—C21A—C20A | 111.4 (4) | C13C—C8C—C7C | 108.4 (4) |
N2A—C21A—H21A | 109.4 | C10C—C9C—C8C | 120.1 (5) |
C20A—C21A—H21A | 109.4 | C10C—C9C—H9C | 120.0 |
N2A—C21A—H21B | 109.4 | C8C—C9C—H9C | 120.0 |
C20A—C21A—H21B | 109.4 | C9C—C10C—C11C | 120.1 (5) |
H21A—C21A—H21B | 108.0 | C9C—C10C—H10C | 119.9 |
O3A—C22A—O4A | 122.3 (5) | C11C—C10C—H10C | 119.9 |
O3A—C22A—C16A | 125.1 (5) | C10C—C11C—C12C | 121.8 (5) |
O4A—C22A—C16A | 112.5 (5) | C10C—C11C—H11C | 119.1 |
O4A—C23A—H23A | 109.5 | C12C—C11C—H11C | 119.1 |
O4A—C23A—H23B | 109.5 | C13C—C12C—C11C | 116.8 (5) |
H23A—C23A—H23B | 109.5 | C13C—C12C—H12C | 121.6 |
O4A—C23A—H23C | 109.5 | C11C—C12C—H12C | 121.6 |
H23A—C23A—H23C | 109.5 | C12C—C13C—N1C | 128.0 (4) |
H23B—C23A—H23C | 109.5 | C12C—C13C—C8C | 122.7 (5) |
C17B—O2B—C19B | 115.8 (4) | N1C—C13C—C8C | 109.3 (4) |
C22B—O4B—C23B | 114.2 (4) | C3C—C14C—C15C | 109.0 (4) |
C2B—N1B—C13B | 111.6 (4) | C3C—C14C—H14E | 109.9 |
C2B—N1B—H1NB | 124.2 | C15C—C14C—H14E | 109.9 |
C13B—N1B—H1NB | 124.2 | C3C—C14C—H14F | 109.9 |
C21B—N2B—C5B | 112.8 (4) | C15C—C14C—H14F | 109.9 |
C21B—N2B—C3B | 111.2 (4) | H14E—C14C—H14F | 108.3 |
C5B—N2B—C3B | 104.4 (4) | C16C—C15C—C14C | 113.0 (4) |
O1B—C2B—N1B | 124.7 (4) | C16C—C15C—C20C | 108.2 (4) |
O1B—C2B—C7B | 127.5 (4) | C14C—C15C—C20C | 111.4 (4) |
N1B—C2B—C7B | 107.7 (4) | C16C—C15C—H15C | 108.0 |
N2B—C3B—C14B | 109.7 (4) | C14C—C15C—H15C | 108.0 |
N2B—C3B—C7B | 101.7 (4) | C20C—C15C—H15C | 108.0 |
C14B—C3B—C7B | 119.9 (4) | C17C—C16C—C22C | 120.5 (5) |
N2B—C3B—H3B | 108.3 | C17C—C16C—C15C | 121.8 (5) |
C14B—C3B—H3B | 108.3 | C22C—C16C—C15C | 117.6 (4) |
C7B—C3B—H3B | 108.3 | C16C—C17C—O2C | 125.7 (5) |
N2B—C5B—C6B | 105.6 (4) | C16C—C17C—H17C | 117.2 |
N2B—C5B—H5B1 | 110.6 | O2C—C17C—H17C | 117.2 |
C6B—C5B—H5B1 | 110.6 | C19C—C18C—H18G | 109.5 |
N2B—C5B—H5B2 | 110.6 | C19C—C18C—H18H | 109.5 |
C6B—C5B—H5B2 | 110.6 | H18G—C18C—H18H | 109.5 |
H5B1—C5B—H5B2 | 108.8 | C19C—C18C—H18I | 109.5 |
C5B—C6B—C7B | 105.0 (4) | H18G—C18C—H18I | 109.5 |
C5B—C6B—H6B1 | 110.8 | H18H—C18C—H18I | 109.5 |
C7B—C6B—H6B1 | 110.8 | O2C—C19C—C18C | 105.2 (4) |
C5B—C6B—H6B2 | 110.8 | O2C—C19C—C20C | 109.2 (4) |
C7B—C6B—H6B2 | 110.8 | C18C—C19C—C20C | 114.6 (4) |
H6B1—C6B—H6B2 | 108.8 | O2C—C19C—H19C | 109.2 |
C8B—C7B—C3B | 117.4 (4) | C18C—C19C—H19C | 109.2 |
C8B—C7B—C2B | 102.7 (3) | C20C—C19C—H19C | 109.2 |
C3B—C7B—C2B | 112.2 (4) | C21C—C20C—C19C | 114.3 (4) |
C8B—C7B—C6B | 113.4 (4) | C21C—C20C—C15C | 110.8 (4) |
C3B—C7B—C6B | 100.9 (3) | C19C—C20C—C15C | 109.9 (4) |
C2B—C7B—C6B | 110.5 (4) | C21C—C20C—H20C | 107.2 |
C9B—C8B—C13B | 120.0 (4) | C19C—C20C—H20C | 107.2 |
C9B—C8B—C7B | 131.9 (4) | C15C—C20C—H20C | 107.2 |
C13B—C8B—C7B | 108.1 (4) | N2C—C21C—C20C | 111.8 (4) |
C8B—C9B—C10B | 118.8 (4) | N2C—C21C—H21E | 109.2 |
C8B—C9B—H9B | 120.6 | C20C—C21C—H21E | 109.2 |
C10B—C9B—H9B | 120.6 | N2C—C21C—H21F | 109.2 |
C11B—C10B—C9B | 120.9 (5) | C20C—C21C—H21F | 109.2 |
C11B—C10B—H10B | 119.6 | H21E—C21C—H21F | 107.9 |
C9B—C10B—H10B | 119.6 | O3C—C22C—O4C | 121.1 (5) |
C10B—C11B—C12B | 121.0 (5) | O3C—C22C—C16C | 124.9 (5) |
C10B—C11B—H11B | 119.5 | O4C—C22C—C16C | 113.9 (4) |
C12B—C11B—H11B | 119.5 | O4C—C23C—H23G | 109.5 |
C13B—C12B—C11B | 116.8 (4) | O4C—C23C—H23H | 109.5 |
C13B—C12B—H12B | 121.6 | H23G—C23C—H23H | 109.5 |
C11B—C12B—H12B | 121.6 | O4C—C23C—H23I | 109.5 |
C12B—C13B—N1B | 127.8 (4) | H23G—C23C—H23I | 109.5 |
C12B—C13B—C8B | 122.5 (5) | H23H—C23C—H23I | 109.5 |
| | | |
C13A—N1A—C2A—O1A | 178.7 (5) | C2B—N1B—C13B—C12B | −178.3 (5) |
C13A—N1A—C2A—C7A | −0.5 (5) | C2B—N1B—C13B—C8B | 1.5 (6) |
C21A—N2A—C3A—C14A | 62.1 (5) | C9B—C8B—C13B—C12B | −0.7 (8) |
C5A—N2A—C3A—C14A | −177.8 (3) | C7B—C8B—C13B—C12B | −177.7 (5) |
C21A—N2A—C3A—C7A | −170.8 (4) | C9B—C8B—C13B—N1B | 179.5 (4) |
C5A—N2A—C3A—C7A | −50.6 (4) | C7B—C8B—C13B—N1B | 2.5 (6) |
C3A—N2A—C5A—C6A | 40.0 (4) | N2B—C3B—C14B—C15B | −58.5 (5) |
C21A—N2A—C5A—C6A | 159.3 (4) | C7B—C3B—C14B—C15B | −175.4 (4) |
N2A—C5A—C6A—C7A | −13.8 (5) | C3B—C14B—C15B—C16B | 176.7 (4) |
O1A—C2A—C7A—C8A | −178.8 (5) | C3B—C14B—C15B—C20B | 54.3 (5) |
N1A—C2A—C7A—C8A | 0.3 (5) | C20B—C15B—C16B—C17B | 17.7 (6) |
O1A—C2A—C7A—C6A | 58.3 (6) | C14B—C15B—C16B—C17B | −106.4 (5) |
N1A—C2A—C7A—C6A | −122.6 (4) | C20B—C15B—C16B—C22B | −160.8 (4) |
O1A—C2A—C7A—C3A | −54.5 (6) | C14B—C15B—C16B—C22B | 75.1 (6) |
N1A—C2A—C7A—C3A | 124.6 (4) | C22B—C16B—C17B—O2B | −177.6 (4) |
C5A—C6A—C7A—C8A | 109.0 (4) | C15B—C16B—C17B—O2B | 3.9 (8) |
C5A—C6A—C7A—C2A | −135.0 (4) | C19B—O2B—C17B—C16B | 7.1 (7) |
C5A—C6A—C7A—C3A | −15.6 (5) | C17B—O2B—C19B—C18B | −164.5 (4) |
N2A—C3A—C7A—C8A | −83.6 (5) | C17B—O2B—C19B—C20B | −38.8 (5) |
C14A—C3A—C7A—C8A | 38.8 (6) | O2B—C19B—C20B—C15B | 60.7 (5) |
N2A—C3A—C7A—C2A | 159.8 (4) | C18B—C19B—C20B—C15B | 179.2 (4) |
C14A—C3A—C7A—C2A | −77.8 (5) | O2B—C19B—C20B—C21B | −174.0 (3) |
N2A—C3A—C7A—C6A | 39.9 (5) | C18B—C19B—C20B—C21B | −55.5 (6) |
C14A—C3A—C7A—C6A | 162.3 (4) | C16B—C15B—C20B—C19B | −48.9 (5) |
C2A—C7A—C8A—C13A | −0.1 (5) | C14B—C15B—C20B—C19B | 76.2 (5) |
C6A—C7A—C8A—C13A | 121.8 (4) | C16B—C15B—C20B—C21B | −176.8 (4) |
C3A—C7A—C8A—C13A | −121.9 (4) | C14B—C15B—C20B—C21B | −51.6 (5) |
C2A—C7A—C8A—C9A | −178.1 (5) | C5B—N2B—C21B—C20B | −177.8 (4) |
C6A—C7A—C8A—C9A | −56.2 (7) | C3B—N2B—C21B—C20B | −60.9 (5) |
C3A—C7A—C8A—C9A | 60.0 (7) | C19B—C20B—C21B—N2B | −71.0 (5) |
C13A—C8A—C9A—C10A | −1.0 (7) | C15B—C20B—C21B—N2B | 54.8 (6) |
C7A—C8A—C9A—C10A | 176.9 (5) | C23B—O4B—C22B—O3B | −3.0 (6) |
C8A—C9A—C10A—C11A | 0.8 (8) | C23B—O4B—C22B—C16B | 175.2 (4) |
C9A—C10A—C11A—C12A | −0.9 (8) | C17B—C16B—C22B—O3B | 169.2 (5) |
C10A—C11A—C12A—C13A | 1.2 (7) | C15B—C16B—C22B—O3B | −12.3 (7) |
C9A—C8A—C13A—C12A | 1.4 (7) | C17B—C16B—C22B—O4B | −9.0 (6) |
C7A—C8A—C13A—C12A | −176.9 (4) | C15B—C16B—C22B—O4B | 169.5 (4) |
C9A—C8A—C13A—N1A | 178.1 (4) | C13C—N1C—C2C—O1C | 178.7 (5) |
C7A—C8A—C13A—N1A | −0.2 (5) | C13C—N1C—C2C—C7C | −1.3 (5) |
C11A—C12A—C13A—C8A | −1.4 (7) | C5C—N2C—C3C—C14C | −175.6 (4) |
C11A—C12A—C13A—N1A | −177.6 (5) | C21C—N2C—C3C—C14C | 63.3 (5) |
C2A—N1A—C13A—C8A | 0.4 (6) | C5C—N2C—C3C—C7C | −48.7 (5) |
C2A—N1A—C13A—C12A | 177.1 (5) | C21C—N2C—C3C—C7C | −169.8 (4) |
N2A—C3A—C14A—C15A | −59.5 (5) | C3C—N2C—C5C—C6C | 38.4 (5) |
C7A—C3A—C14A—C15A | −177.1 (4) | C21C—N2C—C5C—C6C | 158.2 (4) |
C3A—C14A—C15A—C16A | 177.7 (4) | N2C—C5C—C6C—C7C | −12.5 (6) |
C3A—C14A—C15A—C20A | 55.2 (5) | O1C—C2C—C7C—C8C | −178.0 (5) |
C20A—C15A—C16A—C17A | 18.2 (6) | N1C—C2C—C7C—C8C | 2.0 (5) |
C14A—C15A—C16A—C17A | −105.0 (5) | O1C—C2C—C7C—C3C | −54.8 (6) |
C20A—C15A—C16A—C22A | −154.8 (4) | N1C—C2C—C7C—C3C | 125.1 (4) |
C14A—C15A—C16A—C22A | 82.0 (5) | O1C—C2C—C7C—C6C | 57.5 (6) |
C22A—C16A—C17A—O2A | 178.6 (4) | N1C—C2C—C7C—C6C | −122.5 (4) |
C15A—C16A—C17A—O2A | 5.8 (7) | N2C—C3C—C7C—C8C | −86.5 (5) |
C19A—O2A—C17A—C16A | 4.7 (6) | C14C—C3C—C7C—C8C | 35.3 (6) |
C17A—O2A—C19A—C20A | −38.2 (5) | N2C—C3C—C7C—C2C | 158.1 (4) |
C17A—O2A—C19A—C18A | −162.5 (4) | C14C—C3C—C7C—C2C | −80.1 (5) |
O2A—C19A—C20A—C21A | −172.6 (4) | N2C—C3C—C7C—C6C | 38.8 (5) |
C18A—C19A—C20A—C21A | −55.0 (5) | C14C—C3C—C7C—C6C | 160.6 (4) |
O2A—C19A—C20A—C15A | 61.7 (5) | C5C—C6C—C7C—C8C | 109.1 (5) |
C18A—C19A—C20A—C15A | 179.3 (4) | C5C—C6C—C7C—C2C | −133.8 (5) |
C16A—C15A—C20A—C19A | −50.7 (5) | C5C—C6C—C7C—C3C | −16.1 (5) |
C14A—C15A—C20A—C19A | 74.3 (5) | C2C—C7C—C8C—C9C | −179.5 (5) |
C16A—C15A—C20A—C21A | −178.6 (4) | C3C—C7C—C8C—C9C | 60.8 (7) |
C14A—C15A—C20A—C21A | −53.6 (5) | C6C—C7C—C8C—C9C | −56.9 (7) |
C3A—N2A—C21A—C20A | −58.8 (5) | C2C—C7C—C8C—C13C | −2.0 (5) |
C5A—N2A—C21A—C20A | −173.5 (4) | C3C—C7C—C8C—C13C | −121.7 (4) |
C19A—C20A—C21A—N2A | −70.1 (5) | C6C—C7C—C8C—C13C | 120.6 (4) |
C15A—C20A—C21A—N2A | 55.0 (5) | C13C—C8C—C9C—C10C | 1.2 (7) |
C23A—O4A—C22A—O3A | 2.2 (6) | C7C—C8C—C9C—C10C | 178.4 (5) |
C23A—O4A—C22A—C16A | −176.3 (4) | C8C—C9C—C10C—C11C | −1.0 (8) |
C17A—C16A—C22A—O3A | 177.5 (5) | C9C—C10C—C11C—C12C | 0.6 (8) |
C15A—C16A—C22A—O3A | −9.6 (7) | C10C—C11C—C12C—C13C | −0.3 (7) |
C17A—C16A—C22A—O4A | −4.0 (6) | C11C—C12C—C13C—N1C | −179.7 (4) |
C15A—C16A—C22A—O4A | 168.8 (4) | C11C—C12C—C13C—C8C | 0.4 (7) |
C13B—N1B—C2B—O1B | 178.5 (5) | C2C—N1C—C13C—C12C | −179.9 (5) |
C13B—N1B—C2B—C7B | −4.8 (5) | C2C—N1C—C13C—C8C | 0.0 (5) |
C21B—N2B—C3B—C14B | 63.1 (5) | C9C—C8C—C13C—C12C | −0.9 (7) |
C5B—N2B—C3B—C14B | −174.9 (4) | C7C—C8C—C13C—C12C | −178.8 (4) |
C21B—N2B—C3B—C7B | −169.0 (4) | C9C—C8C—C13C—N1C | 179.3 (4) |
C5B—N2B—C3B—C7B | −47.0 (5) | C7C—C8C—C13C—N1C | 1.4 (5) |
C21B—N2B—C5B—C6B | 151.4 (4) | N2C—C3C—C14C—C15C | −59.9 (5) |
C3B—N2B—C5B—C6B | 30.5 (5) | C7C—C3C—C14C—C15C | −176.6 (4) |
N2B—C5B—C6B—C7B | −2.7 (6) | C3C—C14C—C15C—C16C | 175.2 (4) |
N2B—C3B—C7B—C8B | −80.4 (5) | C3C—C14C—C15C—C20C | 53.2 (5) |
C14B—C3B—C7B—C8B | 40.6 (6) | C14C—C15C—C16C—C17C | −109.0 (5) |
N2B—C3B—C7B—C2B | 161.0 (4) | C20C—C15C—C16C—C17C | 14.8 (6) |
C14B—C3B—C7B—C2B | −77.9 (6) | C14C—C15C—C16C—C22C | 75.9 (6) |
N2B—C3B—C7B—C6B | 43.4 (5) | C20C—C15C—C16C—C22C | −160.3 (4) |
C14B—C3B—C7B—C6B | 164.4 (4) | C22C—C16C—C17C—O2C | −178.5 (4) |
O1B—C2B—C7B—C8B | −177.6 (5) | C15C—C16C—C17C—O2C | 6.5 (8) |
N1B—C2B—C7B—C8B | 5.9 (5) | C19C—O2C—C17C—C16C | 7.6 (7) |
O1B—C2B—C7B—C3B | −50.6 (7) | C17C—O2C—C19C—C18C | −165.2 (4) |
N1B—C2B—C7B—C3B | 132.9 (4) | C17C—O2C—C19C—C20C | −41.7 (5) |
O1B—C2B—C7B—C6B | 61.2 (6) | O2C—C19C—C20C—C21C | −172.4 (4) |
N1B—C2B—C7B—C6B | −115.4 (4) | C18C—C19C—C20C—C21C | −54.7 (5) |
C5B—C6B—C7B—C8B | 101.5 (5) | O2C—C19C—C20C—C15C | 62.3 (5) |
C5B—C6B—C7B—C3B | −25.0 (5) | C18C—C19C—C20C—C15C | −180.0 (4) |
C5B—C6B—C7B—C2B | −143.8 (4) | C16C—C15C—C20C—C21C | −174.9 (4) |
C3B—C7B—C8B—C9B | 55.0 (7) | C14C—C15C—C20C—C21C | −50.2 (5) |
C2B—C7B—C8B—C9B | 178.5 (5) | C16C—C15C—C20C—C19C | −47.7 (5) |
C6B—C7B—C8B—C9B | −62.2 (7) | C14C—C15C—C20C—C19C | 77.1 (5) |
C3B—C7B—C8B—C13B | −128.5 (4) | C5C—N2C—C21C—C20C | −175.3 (4) |
C2B—C7B—C8B—C13B | −5.0 (5) | C3C—N2C—C21C—C20C | −59.4 (5) |
C6B—C7B—C8B—C13B | 114.3 (4) | C19C—C20C—C21C—N2C | −72.0 (5) |
C13B—C8B—C9B—C10B | 0.8 (7) | C15C—C20C—C21C—N2C | 52.7 (5) |
C7B—C8B—C9B—C10B | 177.0 (5) | C23C—O4C—C22C—O3C | −0.1 (7) |
C8B—C9B—C10B—C11B | −0.7 (8) | C23C—O4C—C22C—C16C | 179.1 (5) |
C9B—C10B—C11B—C12B | 0.4 (8) | C17C—C16C—C22C—O3C | 176.7 (5) |
C10B—C11B—C12B—C13B | −0.3 (8) | C15C—C16C—C22C—O3C | −8.1 (7) |
C11B—C12B—C13B—N1B | −179.8 (5) | C17C—C16C—C22C—O4C | −2.5 (7) |
C11B—C12B—C13B—C8B | 0.5 (8) | C15C—C16C—C22C—O4C | 172.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1NA···O1C | 0.88 | 1.99 | 2.864 (5) | 171 |
N1B—H1NB···O1A | 0.88 | 2.05 | 2.894 (5) | 161 |
N1C—H1NC···O1Bi | 0.88 | 2.03 | 2.873 (5) | 159 |
C10B—H10B···O2Aii | 0.95 | 2.60 | 3.263 (5) | 127 |
C15C—H15C···O1A | 1.00 | 2.60 | 3.528 (6) | 155 |
C20A—H20A···O1Ciii | 1.00 | 2.59 | 3.459 (6) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) x−1, y, z. |