The title compound, C
27H
31N
3O
5, is also known as 13-oxofumitremorgin B. Intermolecular O—H
O and C—H
O hydrogen bonds stabilize the crystal structure.
Supporting information
CCDC reference: 642925
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.043
- wR factor = 0.124
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.01 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.00 Ratio
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.97
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C26
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 25.01
From the CIF: _reflns_number_total 2517
Count of symmetry unique reflns 2522
Completeness (_total/calc) 99.80%
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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
4 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
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).
5a-Hydroxy-9-methoxy-11-(3-methyl-2-butenyl)-12-(2-methyl-1-propenyl)-
2,3,11,12-tetrahydro-1H,5
H-
pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-
b]indole-
5,6,14(5aH,14aH)-trione
top
Crystal data top
C27H31N3O5 | F(000) = 1016 |
Mr = 477.55 | Dx = 1.270 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3028 reflections |
a = 7.806 (2) Å | θ = 2.4–21.1° |
b = 15.064 (3) Å | µ = 0.09 mm−1 |
c = 21.247 (3) Å | T = 298 K |
V = 2498.4 (9) Å3 | Needle, colorless |
Z = 4 | 0.68 × 0.24 × 0.22 mm |
Data collection top
Bruker APEX area-detector diffractometer | 2517 independent reflections |
Radiation source: fine-focus sealed tube | 1836 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.942, Tmax = 0.981 | k = −17→17 |
12939 measured reflections | l = −25→20 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0523P)2 + 1.178P] where P = (Fo2 + 2Fc2)/3 |
2517 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.27 e Å−3 |
12 restraints | Δρmin = −0.24 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 | |
N1 | −0.1347 (5) | 0.4732 (2) | 0.97817 (15) | 0.0332 (8) | |
N2 | 0.1186 (4) | 0.3039 (2) | 0.89050 (15) | 0.0301 (8) | |
N3 | 0.4265 (4) | 0.2364 (2) | 0.85467 (15) | 0.0364 (8) | |
O1 | −0.0069 (4) | 0.24788 (19) | 0.80268 (13) | 0.0420 (8) | |
O2 | 0.5411 (4) | 0.3259 (2) | 0.92843 (14) | 0.0460 (8) | |
O3 | 0.2211 (4) | 0.19012 (17) | 0.95815 (13) | 0.0372 (7) | |
H3 | 0.1293 | 0.1848 | 0.9765 | 0.056* | |
O4 | 0.3460 (4) | 0.3238 (2) | 1.04003 (15) | 0.0529 (9) | |
O5 | −0.1883 (5) | 0.6221 (2) | 1.18279 (16) | 0.0669 (11) | |
C1 | −0.0158 (5) | 0.4132 (2) | 0.95848 (18) | 0.0297 (9) | |
C2 | −0.0291 (5) | 0.3650 (2) | 0.89757 (17) | 0.0294 (9) | |
H2 | −0.1337 | 0.3290 | 0.8986 | 0.035* | |
C3 | 0.1149 (5) | 0.2507 (2) | 0.83839 (19) | 0.0307 (9) | |
C4 | 0.2753 (5) | 0.1976 (3) | 0.82517 (19) | 0.0344 (10) | |
H4 | 0.2603 | 0.1362 | 0.8393 | 0.041* | |
C5 | 0.3241 (6) | 0.1993 (4) | 0.7553 (2) | 0.0509 (13) | |
H5A | 0.2683 | 0.1516 | 0.7325 | 0.061* | |
H5B | 0.2933 | 0.2556 | 0.7362 | 0.061* | |
C6 | 0.5155 (7) | 0.1869 (4) | 0.7562 (2) | 0.0575 (14) | |
H6A | 0.5447 | 0.1246 | 0.7605 | 0.069* | |
H6B | 0.5669 | 0.2097 | 0.7179 | 0.069* | |
C7 | 0.5752 (6) | 0.2385 (3) | 0.8123 (2) | 0.0479 (12) | |
H7A | 0.6740 | 0.2105 | 0.8317 | 0.057* | |
H7B | 0.6045 | 0.2989 | 0.8008 | 0.057* | |
C8 | 0.4219 (5) | 0.2817 (3) | 0.9080 (2) | 0.0342 (10) | |
C9 | 0.2433 (5) | 0.2790 (2) | 0.93978 (18) | 0.0299 (9) | |
C10 | 0.2409 (6) | 0.3383 (3) | 0.99857 (19) | 0.0357 (10) | |
C11 | 0.1088 (6) | 0.4024 (3) | 1.00415 (19) | 0.0333 (10) | |
C12 | 0.0617 (6) | 0.4590 (3) | 1.05575 (18) | 0.0367 (10) | |
C13 | 0.1294 (7) | 0.4757 (3) | 1.1151 (2) | 0.0486 (13) | |
H13 | 0.2323 | 0.4500 | 1.1275 | 0.058* | |
C14 | 0.0411 (7) | 0.5311 (3) | 1.1550 (2) | 0.0537 (13) | |
H14 | 0.0859 | 0.5431 | 1.1947 | 0.064* | |
C15 | −0.1136 (7) | 0.5697 (3) | 1.1376 (2) | 0.0483 (13) | |
C16 | −0.1813 (6) | 0.5561 (3) | 1.0785 (2) | 0.0429 (12) | |
H16 | −0.2830 | 0.5829 | 1.0659 | 0.051* | |
C17 | −0.0913 (6) | 0.5008 (2) | 1.03895 (18) | 0.0356 (10) | |
C18 | −0.2887 (6) | 0.5043 (3) | 0.9457 (2) | 0.0404 (11) | |
H18A | −0.3865 | 0.4986 | 0.9736 | 0.048* | |
H18B | −0.3092 | 0.4675 | 0.9091 | 0.048* | |
C19 | −0.2718 (7) | 0.5979 (3) | 0.9258 (2) | 0.0542 (14) | |
H19 | −0.1732 | 0.6116 | 0.9032 | 0.065* | |
C20 | −0.3778 (9) | 0.6644 (4) | 0.9357 (3) | 0.077 (2) | |
C21 | −0.3413 (10) | 0.7564 (4) | 0.9104 (3) | 0.105 (2) | |
H21A | −0.2256 | 0.7589 | 0.8952 | 0.158* | |
H21B | −0.3561 | 0.7992 | 0.9434 | 0.158* | |
H21C | −0.4189 | 0.7693 | 0.8766 | 0.158* | |
C22 | −0.5391 (11) | 0.6568 (5) | 0.9719 (4) | 0.117 (3) | |
H22A | −0.5511 | 0.5973 | 0.9873 | 0.175* | |
H22B | −0.6342 | 0.6709 | 0.9451 | 0.175* | |
H22C | −0.5365 | 0.6974 | 1.0068 | 0.175* | |
C23 | −0.0397 (6) | 0.4264 (3) | 0.84068 (19) | 0.0384 (11) | |
H23 | −0.1406 | 0.4232 | 0.8175 | 0.046* | |
C24 | 0.0747 (7) | 0.4830 (3) | 0.8201 (2) | 0.0497 (13) | |
C25 | 0.2459 (9) | 0.4976 (5) | 0.8501 (3) | 0.086 (2) | |
H25A | 0.2436 | 0.4760 | 0.8925 | 0.129* | |
H25B | 0.2719 | 0.5599 | 0.8502 | 0.129* | |
H25C | 0.3320 | 0.4663 | 0.8267 | 0.129* | |
C26 | 0.0457 (9) | 0.5354 (4) | 0.7614 (3) | 0.0783 (19) | |
H26A | −0.0666 | 0.5229 | 0.7452 | 0.117* | |
H26B | 0.1301 | 0.5194 | 0.7305 | 0.117* | |
H26C | 0.0549 | 0.5976 | 0.7706 | 0.117* | |
C27 | −0.3470 (8) | 0.6624 (4) | 1.1680 (3) | 0.0775 (19) | |
H27A | −0.3310 | 0.7044 | 1.1346 | 0.116* | |
H27B | −0.3907 | 0.6924 | 1.2045 | 0.116* | |
H27C | −0.4271 | 0.6177 | 1.1549 | 0.116* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.035 (2) | 0.0304 (17) | 0.0344 (19) | 0.0049 (16) | 0.0007 (16) | 0.0003 (15) |
N2 | 0.0278 (19) | 0.0317 (17) | 0.0308 (18) | 0.0040 (16) | −0.0040 (16) | −0.0009 (15) |
N3 | 0.0246 (19) | 0.046 (2) | 0.038 (2) | 0.0018 (17) | 0.0033 (16) | 0.0012 (17) |
O1 | 0.0299 (17) | 0.0524 (18) | 0.0437 (17) | 0.0034 (15) | −0.0090 (15) | −0.0101 (15) |
O2 | 0.0297 (17) | 0.0566 (19) | 0.0517 (19) | −0.0098 (16) | −0.0041 (16) | 0.0021 (16) |
O3 | 0.0355 (17) | 0.0338 (15) | 0.0423 (17) | 0.0045 (13) | 0.0069 (15) | 0.0078 (13) |
O4 | 0.049 (2) | 0.068 (2) | 0.0419 (19) | 0.0169 (18) | −0.0172 (17) | −0.0064 (17) |
O5 | 0.086 (3) | 0.066 (2) | 0.049 (2) | 0.013 (2) | 0.008 (2) | −0.0210 (18) |
C1 | 0.030 (2) | 0.0266 (19) | 0.033 (2) | −0.0019 (18) | 0.003 (2) | 0.0008 (17) |
C2 | 0.025 (2) | 0.0295 (19) | 0.033 (2) | 0.0031 (18) | 0.0005 (19) | −0.0003 (18) |
C3 | 0.030 (2) | 0.028 (2) | 0.034 (2) | −0.0008 (19) | 0.000 (2) | −0.0012 (18) |
C4 | 0.033 (2) | 0.034 (2) | 0.036 (2) | 0.003 (2) | 0.003 (2) | −0.0027 (19) |
C5 | 0.046 (3) | 0.067 (3) | 0.039 (3) | 0.008 (3) | 0.002 (2) | −0.008 (2) |
C6 | 0.050 (3) | 0.075 (3) | 0.047 (3) | 0.007 (3) | 0.014 (3) | −0.004 (3) |
C7 | 0.032 (3) | 0.061 (3) | 0.050 (3) | 0.001 (2) | 0.014 (2) | 0.005 (2) |
C8 | 0.029 (2) | 0.034 (2) | 0.039 (2) | 0.002 (2) | 0.001 (2) | 0.0081 (19) |
C9 | 0.027 (2) | 0.030 (2) | 0.033 (2) | 0.0027 (17) | −0.0014 (19) | 0.0020 (17) |
C10 | 0.036 (3) | 0.041 (2) | 0.031 (2) | 0.002 (2) | −0.005 (2) | 0.0053 (19) |
C11 | 0.036 (3) | 0.031 (2) | 0.033 (2) | −0.0012 (19) | 0.000 (2) | 0.0005 (17) |
C12 | 0.044 (3) | 0.032 (2) | 0.034 (2) | 0.000 (2) | 0.000 (2) | −0.0004 (19) |
C13 | 0.063 (3) | 0.041 (2) | 0.042 (3) | 0.005 (2) | −0.011 (3) | −0.001 (2) |
C14 | 0.076 (4) | 0.044 (3) | 0.041 (3) | −0.002 (3) | −0.008 (3) | −0.004 (2) |
C15 | 0.071 (4) | 0.035 (2) | 0.039 (3) | 0.002 (3) | 0.008 (3) | −0.007 (2) |
C16 | 0.056 (3) | 0.032 (2) | 0.041 (3) | 0.005 (2) | 0.007 (2) | −0.003 (2) |
C17 | 0.048 (3) | 0.0250 (19) | 0.034 (2) | 0.000 (2) | 0.004 (2) | 0.0006 (18) |
C18 | 0.034 (3) | 0.042 (2) | 0.045 (3) | 0.007 (2) | −0.002 (2) | −0.005 (2) |
C19 | 0.064 (4) | 0.045 (3) | 0.054 (3) | 0.022 (3) | −0.017 (3) | −0.003 (2) |
C20 | 0.107 (5) | 0.063 (3) | 0.061 (4) | 0.037 (4) | −0.039 (4) | −0.019 (3) |
C21 | 0.133 (5) | 0.077 (3) | 0.106 (4) | 0.026 (4) | −0.032 (4) | −0.002 (3) |
C22 | 0.102 (4) | 0.130 (5) | 0.119 (4) | 0.040 (4) | −0.003 (4) | −0.022 (4) |
C23 | 0.039 (3) | 0.038 (2) | 0.038 (2) | 0.009 (2) | −0.002 (2) | 0.000 (2) |
C24 | 0.054 (3) | 0.048 (3) | 0.047 (3) | 0.005 (3) | 0.009 (3) | 0.009 (2) |
C25 | 0.085 (5) | 0.090 (4) | 0.083 (4) | −0.036 (4) | −0.007 (4) | 0.038 (4) |
C26 | 0.092 (5) | 0.075 (4) | 0.068 (4) | 0.018 (4) | 0.021 (4) | 0.033 (3) |
C27 | 0.083 (5) | 0.080 (4) | 0.069 (4) | 0.019 (4) | 0.016 (4) | −0.022 (3) |
Geometric parameters (Å, º) top
N1—C1 | 1.361 (5) | C12—C13 | 1.390 (6) |
N1—C17 | 1.399 (5) | C12—C17 | 1.396 (6) |
N1—C18 | 1.463 (5) | C13—C14 | 1.375 (6) |
N2—C3 | 1.367 (5) | C13—H13 | 0.9300 |
N2—C9 | 1.478 (5) | C14—C15 | 1.390 (7) |
N2—C2 | 1.483 (5) | C14—H14 | 0.9300 |
N3—C8 | 1.323 (5) | C15—C16 | 1.378 (6) |
N3—C4 | 1.459 (5) | C16—C17 | 1.375 (6) |
N3—C7 | 1.469 (5) | C16—H16 | 0.9300 |
O1—C3 | 1.217 (5) | C18—C19 | 1.477 (6) |
O2—C8 | 1.224 (5) | C18—H18A | 0.9700 |
O3—C9 | 1.405 (5) | C18—H18B | 0.9700 |
O3—H3 | 0.8200 | C19—C20 | 1.317 (7) |
O4—C10 | 1.224 (5) | C19—H19 | 0.9300 |
O5—C15 | 1.373 (5) | C20—C22 | 1.480 (10) |
O5—C27 | 1.415 (7) | C20—C21 | 1.513 (9) |
C1—C11 | 1.383 (6) | C21—H21A | 0.9600 |
C1—C2 | 1.488 (5) | C21—H21B | 0.9600 |
C2—C23 | 1.525 (5) | C21—H21C | 0.9600 |
C2—H2 | 0.9800 | C22—H22A | 0.9600 |
C3—C4 | 1.513 (5) | C22—H22B | 0.9600 |
C4—C5 | 1.533 (6) | C22—H22C | 0.9600 |
C4—H4 | 0.9800 | C23—C24 | 1.311 (6) |
C5—C6 | 1.506 (7) | C23—H23 | 0.9300 |
C5—H5A | 0.9700 | C24—C26 | 1.494 (6) |
C5—H5B | 0.9700 | C24—C25 | 1.496 (8) |
C6—C7 | 1.497 (7) | C25—H25A | 0.9600 |
C6—H6A | 0.9700 | C25—H25B | 0.9600 |
C6—H6B | 0.9700 | C25—H25C | 0.9600 |
C7—H7A | 0.9700 | C26—H26A | 0.9600 |
C7—H7B | 0.9700 | C26—H26B | 0.9600 |
C8—C9 | 1.550 (6) | C26—H26C | 0.9600 |
C9—C10 | 1.536 (6) | C27—H27A | 0.9600 |
C10—C11 | 1.418 (6) | C27—H27B | 0.9600 |
C11—C12 | 1.437 (5) | C27—H27C | 0.9600 |
| | | |
C1—N1—C17 | 108.4 (3) | C17—C12—C11 | 106.9 (4) |
C1—N1—C18 | 128.9 (3) | C14—C13—C12 | 118.6 (5) |
C17—N1—C18 | 122.6 (3) | C14—C13—H13 | 120.7 |
C3—N2—C9 | 116.0 (3) | C12—C13—H13 | 120.7 |
C3—N2—C2 | 115.4 (3) | C13—C14—C15 | 121.7 (4) |
C9—N2—C2 | 126.7 (3) | C13—C14—H14 | 119.2 |
C8—N3—C4 | 123.6 (3) | C15—C14—H14 | 119.2 |
C8—N3—C7 | 122.3 (4) | O5—C15—C16 | 124.1 (5) |
C4—N3—C7 | 112.6 (3) | O5—C15—C14 | 115.0 (4) |
C9—O3—H3 | 109.5 | C16—C15—C14 | 120.9 (4) |
C15—O5—C27 | 117.6 (4) | C17—C16—C15 | 116.8 (4) |
N1—C1—C11 | 110.0 (3) | C17—C16—H16 | 121.6 |
N1—C1—C2 | 123.0 (4) | C15—C16—H16 | 121.6 |
C11—C1—C2 | 127.0 (4) | C16—C17—C12 | 123.6 (4) |
N2—C2—C1 | 109.7 (3) | C16—C17—N1 | 128.3 (4) |
N2—C2—C23 | 109.8 (3) | C12—C17—N1 | 108.0 (3) |
C1—C2—C23 | 113.4 (3) | N1—C18—C19 | 111.6 (4) |
N2—C2—H2 | 108.0 | N1—C18—H18A | 109.3 |
C1—C2—H2 | 108.0 | C19—C18—H18A | 109.3 |
C23—C2—H2 | 108.0 | N1—C18—H18B | 109.3 |
O1—C3—N2 | 122.8 (4) | C19—C18—H18B | 109.3 |
O1—C3—C4 | 120.8 (3) | H18A—C18—H18B | 108.0 |
N2—C3—C4 | 116.3 (4) | C20—C19—C18 | 128.6 (6) |
N3—C4—C3 | 112.2 (3) | C20—C19—H19 | 115.7 |
N3—C4—C5 | 102.0 (3) | C18—C19—H19 | 115.7 |
C3—C4—C5 | 112.1 (4) | C19—C20—C22 | 124.0 (6) |
N3—C4—H4 | 110.1 | C19—C20—C21 | 121.4 (7) |
C3—C4—H4 | 110.1 | C22—C20—C21 | 114.6 (6) |
C5—C4—H4 | 110.1 | C20—C21—H21A | 109.5 |
C6—C5—C4 | 103.4 (4) | C20—C21—H21B | 109.5 |
C6—C5—H5A | 111.1 | H21A—C21—H21B | 109.5 |
C4—C5—H5A | 111.1 | C20—C21—H21C | 109.5 |
C6—C5—H5B | 111.1 | H21A—C21—H21C | 109.5 |
C4—C5—H5B | 111.1 | H21B—C21—H21C | 109.5 |
H5A—C5—H5B | 109.0 | C20—C22—H22A | 109.5 |
C7—C6—C5 | 104.8 (4) | C20—C22—H22B | 109.5 |
C7—C6—H6A | 110.8 | H22A—C22—H22B | 109.5 |
C5—C6—H6A | 110.8 | C20—C22—H22C | 109.5 |
C7—C6—H6B | 110.8 | H22A—C22—H22C | 109.5 |
C5—C6—H6B | 110.8 | H22B—C22—H22C | 109.5 |
H6A—C6—H6B | 108.9 | C24—C23—C2 | 128.5 (4) |
N3—C7—C6 | 103.3 (4) | C24—C23—H23 | 115.7 |
N3—C7—H7A | 111.1 | C2—C23—H23 | 115.7 |
C6—C7—H7A | 111.1 | C23—C24—C26 | 121.3 (5) |
N3—C7—H7B | 111.1 | C23—C24—C25 | 124.2 (4) |
C6—C7—H7B | 111.1 | C26—C24—C25 | 114.4 (5) |
H7A—C7—H7B | 109.1 | C24—C25—H25A | 109.5 |
O2—C8—N3 | 124.3 (4) | C24—C25—H25B | 109.5 |
O2—C8—C9 | 123.0 (4) | H25A—C25—H25B | 109.5 |
N3—C8—C9 | 112.6 (4) | C24—C25—H25C | 109.5 |
O3—C9—N2 | 111.0 (3) | H25A—C25—H25C | 109.5 |
O3—C9—C10 | 109.1 (3) | H25B—C25—H25C | 109.5 |
N2—C9—C10 | 114.9 (3) | C24—C26—H26A | 109.5 |
O3—C9—C8 | 104.9 (3) | C24—C26—H26B | 109.5 |
N2—C9—C8 | 106.1 (3) | H26A—C26—H26B | 109.5 |
C10—C9—C8 | 110.5 (3) | C24—C26—H26C | 109.5 |
O4—C10—C11 | 123.3 (4) | H26A—C26—H26C | 109.5 |
O4—C10—C9 | 118.3 (4) | H26B—C26—H26C | 109.5 |
C11—C10—C9 | 118.2 (4) | O5—C27—H27A | 109.5 |
C1—C11—C10 | 122.2 (4) | O5—C27—H27B | 109.5 |
C1—C11—C12 | 106.6 (4) | H27A—C27—H27B | 109.5 |
C10—C11—C12 | 130.8 (4) | O5—C27—H27C | 109.5 |
C13—C12—C17 | 118.4 (4) | H27A—C27—H27C | 109.5 |
C13—C12—C11 | 134.6 (4) | H27B—C27—H27C | 109.5 |
| | | |
C17—N1—C1—C11 | −1.8 (4) | O3—C9—C10—O4 | 57.9 (5) |
C18—N1—C1—C11 | −179.4 (4) | N2—C9—C10—O4 | −176.8 (4) |
C17—N1—C1—C2 | 175.4 (3) | C8—C9—C10—O4 | −56.9 (5) |
C18—N1—C1—C2 | −2.2 (6) | O3—C9—C10—C11 | −117.3 (4) |
C3—N2—C2—C1 | 175.4 (3) | N2—C9—C10—C11 | 8.0 (5) |
C9—N2—C2—C1 | 11.6 (5) | C8—C9—C10—C11 | 127.9 (4) |
C3—N2—C2—C23 | −59.4 (4) | N1—C1—C11—C10 | 174.5 (4) |
C9—N2—C2—C23 | 136.8 (4) | C2—C1—C11—C10 | −2.5 (6) |
N1—C1—C2—N2 | −179.2 (3) | N1—C1—C11—C12 | 0.7 (5) |
C11—C1—C2—N2 | −2.6 (5) | C2—C1—C11—C12 | −176.3 (4) |
N1—C1—C2—C23 | 57.7 (5) | O4—C10—C11—C1 | −175.3 (4) |
C11—C1—C2—C23 | −125.7 (4) | C9—C10—C11—C1 | −0.4 (6) |
C9—N2—C3—O1 | 159.9 (4) | O4—C10—C11—C12 | −3.1 (7) |
C2—N2—C3—O1 | −5.7 (6) | C9—C10—C11—C12 | 171.8 (4) |
C9—N2—C3—C4 | −22.8 (5) | C1—C11—C12—C13 | 177.6 (5) |
C2—N2—C3—C4 | 171.6 (3) | C10—C11—C12—C13 | 4.5 (8) |
C8—N3—C4—C3 | 30.8 (5) | C1—C11—C12—C17 | 0.7 (4) |
C7—N3—C4—C3 | −135.7 (4) | C10—C11—C12—C17 | −172.4 (4) |
C8—N3—C4—C5 | 150.9 (4) | C17—C12—C13—C14 | 1.3 (6) |
C7—N3—C4—C5 | −15.6 (5) | C11—C12—C13—C14 | −175.3 (5) |
O1—C3—C4—N3 | 155.0 (4) | C12—C13—C14—C15 | 0.5 (7) |
N2—C3—C4—N3 | −22.4 (5) | C27—O5—C15—C16 | 1.8 (7) |
O1—C3—C4—C5 | 40.9 (6) | C27—O5—C15—C14 | −179.3 (4) |
N2—C3—C4—C5 | −136.5 (4) | C13—C14—C15—O5 | 178.8 (4) |
N3—C4—C5—C6 | 32.0 (5) | C13—C14—C15—C16 | −2.2 (7) |
C3—C4—C5—C6 | 152.2 (4) | O5—C15—C16—C17 | −179.3 (4) |
C4—C5—C6—C7 | −37.8 (5) | C14—C15—C16—C17 | 1.8 (6) |
C8—N3—C7—C6 | −174.0 (4) | C15—C16—C17—C12 | 0.1 (6) |
C4—N3—C7—C6 | −7.4 (5) | C15—C16—C17—N1 | 177.1 (4) |
C5—C6—C7—N3 | 27.8 (5) | C13—C12—C17—C16 | −1.7 (6) |
C4—N3—C8—O2 | −168.4 (4) | C11—C12—C17—C16 | 175.8 (4) |
C7—N3—C8—O2 | −3.2 (6) | C13—C12—C17—N1 | −179.3 (4) |
C4—N3—C8—C9 | 7.1 (5) | C11—C12—C17—N1 | −1.8 (4) |
C7—N3—C8—C9 | 172.3 (4) | C1—N1—C17—C16 | −175.2 (4) |
C3—N2—C9—O3 | −54.0 (4) | C18—N1—C17—C16 | 2.6 (6) |
C2—N2—C9—O3 | 109.7 (4) | C1—N1—C17—C12 | 2.2 (4) |
C3—N2—C9—C10 | −178.3 (3) | C18—N1—C17—C12 | 180.0 (3) |
C2—N2—C9—C10 | −14.6 (5) | C1—N1—C18—C19 | −110.5 (5) |
C3—N2—C9—C8 | 59.4 (4) | C17—N1—C18—C19 | 72.3 (5) |
C2—N2—C9—C8 | −136.9 (4) | N1—C18—C19—C20 | −128.8 (5) |
O2—C8—C9—O3 | −117.4 (4) | C18—C19—C20—C22 | 1.6 (9) |
N3—C8—C9—O3 | 67.0 (4) | C18—C19—C20—C21 | −178.7 (5) |
O2—C8—C9—N2 | 125.0 (4) | N2—C2—C23—C24 | −59.8 (5) |
N3—C8—C9—N2 | −50.5 (4) | C1—C2—C23—C24 | 63.3 (6) |
O2—C8—C9—C10 | 0.0 (5) | C2—C23—C24—C26 | 177.2 (4) |
N3—C8—C9—C10 | −175.6 (3) | C2—C23—C24—C25 | 0.7 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 2.14 | 2.800 (4) | 138 |
O3—H3···O4i | 0.82 | 2.24 | 2.936 (5) | 143 |
C27—H27B···O1ii | 0.96 | 2.41 | 3.364 (6) | 173 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) −x−1/2, −y+1, z+1/2. |