The title compound, C27H43NO2·H2O, is the monohydrate of a common naturally occurring steroidal alkaloid, for which an X-ray crystal structure has previously been published [Turdybekov, Lindeman, Struchkov, Gazaliev, Balitskii & Zhurinov (1989). Chem. Nat. Compd. 25, 75–76]. This paper reports the correct structure of the title compound and proposes an alternative interpretation of the structure reported in the 1989 paper.
Supporting information
CCDC reference: 624515
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.096
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N26 - H26 ... ?
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 25.00
From the CIF: _reflns_number_total 2517
Count of symmetry unique reflns 2520
Completeness (_total/calc) 99.88%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
12 ALERT level G = General alerts; check
11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.
[(22
R,25
R)-spirosol-5-en-3
β-ol] monohydrate
top
Crystal data top
C27H43NO2·H2O | F(000) = 952 |
Mr = 431.64 | Dx = 1.166 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 50 reflections |
a = 7.6497 (8) Å | θ = 4.8–12.3° |
b = 9.6076 (17) Å | µ = 0.07 mm−1 |
c = 33.445 (5) Å | T = 296 K |
V = 2458.0 (6) Å3 | Block, colourless |
Z = 4 | 0.60 × 0.50 × 0.18 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 25.0°, θmin = 2.4° |
Graphite monochromator | h = −9→2 |
ω scans | k = −1→11 |
3574 measured reflections | l = −39→1 |
2517 independent reflections | 3 standard reflections every 97 reflections |
2112 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: see text |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0474P)2 + 0.2778P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2517 reflections | Δρmax = 0.15 e Å−3 |
285 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (5) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1720 (3) | 0.4677 (3) | 0.62631 (6) | 0.0465 (6) | |
H1A | 0.0619 | 0.5123 | 0.6198 | 0.056* | |
H1B | 0.1608 | 0.3697 | 0.6197 | 0.056* | |
C2 | 0.2029 (3) | 0.4811 (3) | 0.67144 (6) | 0.0460 (6) | |
H2A | 0.2051 | 0.5786 | 0.6789 | 0.055* | |
H2B | 0.1084 | 0.4363 | 0.6859 | 0.055* | |
C3 | 0.3739 (4) | 0.4138 (3) | 0.68227 (7) | 0.0457 (6) | |
H3A | 0.3705 | 0.3159 | 0.6741 | 0.055* | |
C4 | 0.5218 (3) | 0.4860 (3) | 0.66016 (6) | 0.0494 (7) | |
H4A | 0.6313 | 0.4403 | 0.6666 | 0.059* | |
H4B | 0.5297 | 0.5818 | 0.6692 | 0.059* | |
C5 | 0.4948 (3) | 0.4838 (3) | 0.61505 (6) | 0.0392 (6) | |
C6 | 0.6211 (3) | 0.4431 (3) | 0.59106 (7) | 0.0449 (6) | |
H6A | 0.7255 | 0.4156 | 0.6029 | 0.054* | |
C7 | 0.6119 (3) | 0.4370 (3) | 0.54630 (6) | 0.0465 (6) | |
H7A | 0.6124 | 0.3403 | 0.5380 | 0.056* | |
H7B | 0.7153 | 0.4810 | 0.5353 | 0.056* | |
C8 | 0.4505 (3) | 0.5079 (3) | 0.52922 (6) | 0.0356 (5) | |
H8A | 0.4721 | 0.6084 | 0.5282 | 0.043* | |
C9 | 0.2900 (3) | 0.4817 (3) | 0.55588 (6) | 0.0376 (5) | |
H9A | 0.2748 | 0.3805 | 0.5571 | 0.045* | |
C10 | 0.3167 (3) | 0.5314 (2) | 0.59981 (6) | 0.0364 (5) | |
C11 | 0.1229 (3) | 0.5402 (3) | 0.53677 (7) | 0.0521 (7) | |
H11A | 0.1282 | 0.6410 | 0.5373 | 0.062* | |
H11B | 0.0232 | 0.5117 | 0.5527 | 0.062* | |
C12 | 0.0941 (3) | 0.4922 (3) | 0.49324 (7) | 0.0503 (7) | |
H12A | 0.0714 | 0.3928 | 0.4929 | 0.060* | |
H12B | −0.0076 | 0.5390 | 0.4823 | 0.060* | |
C13 | 0.2522 (3) | 0.5235 (3) | 0.46711 (6) | 0.0365 (5) | |
C14 | 0.4129 (3) | 0.4565 (3) | 0.48700 (6) | 0.0358 (5) | |
H14A | 0.3851 | 0.3574 | 0.4896 | 0.043* | |
C15 | 0.5548 (3) | 0.4655 (3) | 0.45487 (6) | 0.0438 (6) | |
H15A | 0.6039 | 0.5584 | 0.4533 | 0.053* | |
H15B | 0.6479 | 0.3992 | 0.4598 | 0.053* | |
C16 | 0.4534 (3) | 0.4289 (3) | 0.41692 (7) | 0.0409 (6) | |
H16A | 0.4769 | 0.3324 | 0.4091 | 0.049* | |
C17 | 0.2563 (3) | 0.4488 (3) | 0.42570 (6) | 0.0375 (6) | |
H17A | 0.2011 | 0.3572 | 0.4283 | 0.045* | |
C18 | 0.2747 (4) | 0.6812 (3) | 0.46208 (7) | 0.0488 (7) | |
H18A | 0.3010 | 0.7224 | 0.4875 | 0.073* | |
H18B | 0.1685 | 0.7206 | 0.4518 | 0.073* | |
H18C | 0.3686 | 0.6994 | 0.4438 | 0.073* | |
C19 | 0.3085 (4) | 0.6924 (3) | 0.60309 (8) | 0.0504 (7) | |
H19A | 0.3499 | 0.7208 | 0.6289 | 0.076* | |
H19B | 0.1899 | 0.7229 | 0.5996 | 0.076* | |
H19C | 0.3806 | 0.7332 | 0.5827 | 0.076* | |
C20 | 0.1853 (3) | 0.5211 (3) | 0.38776 (6) | 0.0418 (6) | |
H20A | 0.1641 | 0.6189 | 0.3946 | 0.050* | |
C21 | 0.0128 (3) | 0.4609 (4) | 0.37226 (8) | 0.0614 (8) | |
H21A | −0.0784 | 0.4791 | 0.3913 | 0.092* | |
H21B | 0.0248 | 0.3623 | 0.3686 | 0.092* | |
H21C | −0.0162 | 0.5036 | 0.3472 | 0.092* | |
C22 | 0.3402 (3) | 0.5173 (3) | 0.35843 (6) | 0.0409 (6) | |
O22 | 0.4914 (2) | 0.5206 (2) | 0.38464 (4) | 0.0449 (4) | |
C23 | 0.3560 (4) | 0.6423 (3) | 0.33119 (8) | 0.0534 (7) | |
H23A | 0.3650 | 0.7259 | 0.3473 | 0.064* | |
H23B | 0.2511 | 0.6498 | 0.3150 | 0.064* | |
C24 | 0.5145 (4) | 0.6329 (3) | 0.30381 (8) | 0.0568 (8) | |
H24A | 0.5135 | 0.7107 | 0.2853 | 0.068* | |
H24B | 0.6203 | 0.6391 | 0.3197 | 0.068* | |
C25 | 0.5157 (3) | 0.4980 (3) | 0.28042 (7) | 0.0532 (7) | |
H25A | 0.4146 | 0.4978 | 0.2624 | 0.064* | |
C26 | 0.4973 (4) | 0.3767 (3) | 0.30909 (7) | 0.0510 (7) | |
H26A | 0.4917 | 0.2904 | 0.2941 | 0.061* | |
H26B | 0.5989 | 0.3727 | 0.3264 | 0.061* | |
N26 | 0.3380 (3) | 0.3918 (2) | 0.33355 (6) | 0.0445 (5) | |
H26 | 0.3215 | 0.3172 | 0.3498 | 0.067* | |
C27 | 0.6812 (4) | 0.4830 (4) | 0.25513 (9) | 0.0778 (10) | |
H27A | 0.6909 | 0.5609 | 0.2373 | 0.117* | |
H27B | 0.6751 | 0.3984 | 0.2399 | 0.117* | |
H27C | 0.7816 | 0.4801 | 0.2723 | 0.117* | |
O28 | 0.3992 (3) | 0.4207 (2) | 0.72466 (4) | 0.0573 (5) | |
H28 | 0.4644 | 0.3564 | 0.7293 | 0.086* | |
O29 | 0.5976 (3) | 0.1785 (2) | 0.73250 (6) | 0.0683 (6) | |
H29A | 0.6689 | 0.1459 | 0.7126 | 0.102* | |
H29B | 0.5722 | 0.1037 | 0.7457 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0394 (13) | 0.0608 (16) | 0.0393 (11) | −0.0057 (14) | 0.0007 (11) | −0.0028 (12) |
C2 | 0.0470 (14) | 0.0509 (15) | 0.0402 (12) | −0.0028 (14) | 0.0087 (11) | −0.0014 (12) |
C3 | 0.0586 (16) | 0.0446 (14) | 0.0339 (11) | 0.0032 (14) | 0.0025 (12) | −0.0044 (11) |
C4 | 0.0444 (14) | 0.0647 (18) | 0.0391 (12) | 0.0007 (15) | −0.0035 (11) | −0.0077 (13) |
C5 | 0.0370 (13) | 0.0443 (14) | 0.0363 (11) | −0.0058 (13) | −0.0007 (11) | −0.0019 (11) |
C6 | 0.0378 (14) | 0.0593 (16) | 0.0376 (12) | 0.0043 (13) | −0.0040 (11) | 0.0015 (12) |
C7 | 0.0416 (14) | 0.0608 (16) | 0.0371 (12) | 0.0092 (13) | 0.0003 (11) | 0.0015 (12) |
C8 | 0.0339 (12) | 0.0384 (12) | 0.0346 (10) | −0.0006 (12) | −0.0009 (10) | −0.0023 (11) |
C9 | 0.0339 (12) | 0.0422 (13) | 0.0368 (11) | −0.0029 (12) | 0.0006 (10) | −0.0042 (11) |
C10 | 0.0349 (12) | 0.0395 (12) | 0.0347 (10) | −0.0009 (12) | 0.0014 (10) | −0.0032 (10) |
C11 | 0.0346 (13) | 0.0824 (19) | 0.0392 (12) | 0.0048 (15) | 0.0013 (11) | −0.0110 (14) |
C12 | 0.0358 (13) | 0.075 (2) | 0.0404 (12) | −0.0008 (15) | −0.0028 (11) | −0.0055 (14) |
C13 | 0.0317 (12) | 0.0411 (13) | 0.0369 (11) | −0.0003 (12) | −0.0025 (10) | −0.0069 (11) |
C14 | 0.0358 (13) | 0.0365 (12) | 0.0350 (11) | 0.0012 (11) | 0.0008 (10) | −0.0018 (10) |
C15 | 0.0384 (13) | 0.0562 (15) | 0.0368 (11) | 0.0105 (13) | 0.0004 (11) | 0.0002 (12) |
C16 | 0.0450 (14) | 0.0430 (14) | 0.0348 (11) | 0.0046 (12) | 0.0036 (11) | 0.0000 (11) |
C17 | 0.0411 (13) | 0.0357 (13) | 0.0357 (11) | −0.0005 (12) | −0.0004 (11) | −0.0036 (10) |
C18 | 0.0550 (17) | 0.0440 (14) | 0.0473 (14) | 0.0107 (13) | −0.0116 (13) | −0.0060 (12) |
C19 | 0.0624 (18) | 0.0464 (14) | 0.0425 (13) | −0.0010 (15) | 0.0017 (14) | −0.0050 (12) |
C20 | 0.0434 (13) | 0.0452 (13) | 0.0369 (11) | 0.0039 (13) | −0.0056 (11) | −0.0041 (12) |
C21 | 0.0495 (16) | 0.086 (2) | 0.0486 (14) | −0.0030 (17) | −0.0084 (13) | −0.0096 (15) |
C22 | 0.0459 (13) | 0.0416 (13) | 0.0351 (11) | 0.0002 (13) | −0.0076 (11) | −0.0005 (11) |
O22 | 0.0436 (9) | 0.0568 (11) | 0.0345 (8) | −0.0025 (10) | −0.0021 (7) | 0.0023 (8) |
C23 | 0.0668 (19) | 0.0447 (14) | 0.0486 (14) | 0.0035 (15) | −0.0065 (15) | 0.0045 (12) |
C24 | 0.0643 (19) | 0.0588 (17) | 0.0472 (15) | −0.0067 (16) | −0.0035 (16) | 0.0142 (13) |
C25 | 0.0470 (15) | 0.0742 (19) | 0.0384 (12) | −0.0034 (16) | −0.0009 (12) | 0.0004 (14) |
C26 | 0.0539 (17) | 0.0548 (16) | 0.0443 (14) | 0.0094 (15) | −0.0010 (14) | −0.0045 (12) |
N26 | 0.0549 (13) | 0.0422 (11) | 0.0363 (10) | 0.0004 (11) | 0.0004 (11) | −0.0002 (9) |
C27 | 0.0602 (19) | 0.105 (3) | 0.0687 (17) | −0.012 (2) | 0.0128 (16) | −0.002 (2) |
O28 | 0.0734 (13) | 0.0664 (12) | 0.0321 (8) | 0.0150 (11) | 0.0008 (9) | −0.0052 (8) |
O29 | 0.0721 (14) | 0.0684 (13) | 0.0644 (12) | 0.0175 (12) | 0.0176 (11) | 0.0107 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.533 (3) | C15—H15B | 0.9700 |
C1—C10 | 1.545 (3) | C16—O22 | 1.423 (3) |
C1—H1A | 0.9700 | C16—C17 | 1.548 (3) |
C1—H1B | 0.9700 | C16—H16A | 0.9800 |
C2—C3 | 1.503 (4) | C17—C20 | 1.545 (3) |
C2—H2A | 0.9700 | C17—H17A | 0.9800 |
C2—H2B | 0.9700 | C18—H18A | 0.9600 |
C3—O28 | 1.432 (3) | C18—H18B | 0.9600 |
C3—C4 | 1.519 (4) | C18—H18C | 0.9600 |
C3—H3A | 0.9800 | C19—H19A | 0.9600 |
C4—C5 | 1.523 (3) | C19—H19B | 0.9600 |
C4—H4A | 0.9700 | C19—H19C | 0.9600 |
C4—H4B | 0.9700 | C20—C21 | 1.531 (4) |
C5—C6 | 1.315 (3) | C20—C22 | 1.539 (3) |
C5—C10 | 1.525 (3) | C20—H20A | 0.9800 |
C6—C7 | 1.500 (3) | C21—H21A | 0.9600 |
C6—H6A | 0.9300 | C21—H21B | 0.9600 |
C7—C8 | 1.521 (3) | C21—H21C | 0.9600 |
C7—H7A | 0.9700 | C22—O22 | 1.451 (3) |
C7—H7B | 0.9700 | C22—N26 | 1.465 (3) |
C8—C14 | 1.524 (3) | C22—C23 | 1.512 (3) |
C8—C9 | 1.538 (3) | C23—C24 | 1.522 (4) |
C8—H8A | 0.9800 | C23—H23A | 0.9700 |
C9—C11 | 1.536 (3) | C23—H23B | 0.9700 |
C9—C10 | 1.558 (3) | C24—C25 | 1.514 (4) |
C9—H9A | 0.9800 | C24—H24A | 0.9700 |
C10—C19 | 1.552 (3) | C24—H24B | 0.9700 |
C11—C12 | 1.543 (3) | C25—C26 | 1.516 (4) |
C11—H11A | 0.9700 | C25—C27 | 1.529 (4) |
C11—H11B | 0.9700 | C25—H25A | 0.9800 |
C12—C13 | 1.522 (3) | C26—N26 | 1.475 (3) |
C12—H12A | 0.9700 | C26—H26A | 0.9700 |
C12—H12B | 0.9700 | C26—H26B | 0.9700 |
C13—C18 | 1.535 (4) | N26—H26 | 0.9078 |
C13—C14 | 1.539 (3) | C27—H27A | 0.9600 |
C13—C17 | 1.560 (3) | C27—H27B | 0.9600 |
C14—C15 | 1.530 (3) | C27—H27C | 0.9600 |
C14—H14A | 0.9800 | O28—H28 | 0.8088 |
C15—C16 | 1.528 (3) | O29—H29A | 0.9164 |
C15—H15A | 0.9700 | O29—H29B | 0.8650 |
| | | |
C2—C1—C10 | 114.9 (2) | C16—C15—H15B | 111.3 |
C2—C1—H1A | 108.5 | C14—C15—H15B | 111.3 |
C10—C1—H1A | 108.5 | H15A—C15—H15B | 109.2 |
C2—C1—H1B | 108.5 | O22—C16—C15 | 112.6 (2) |
C10—C1—H1B | 108.5 | O22—C16—C17 | 105.4 (2) |
H1A—C1—H1B | 107.5 | C15—C16—C17 | 107.95 (18) |
C3—C2—C1 | 109.6 (2) | O22—C16—H16A | 110.2 |
C3—C2—H2A | 109.8 | C15—C16—H16A | 110.2 |
C1—C2—H2A | 109.8 | C17—C16—H16A | 110.2 |
C3—C2—H2B | 109.8 | C20—C17—C16 | 104.01 (19) |
C1—C2—H2B | 109.8 | C20—C17—C13 | 121.0 (2) |
H2A—C2—H2B | 108.2 | C16—C17—C13 | 104.18 (18) |
O28—C3—C2 | 109.7 (2) | C20—C17—H17A | 109.0 |
O28—C3—C4 | 111.1 (2) | C16—C17—H17A | 109.0 |
C2—C3—C4 | 109.5 (2) | C13—C17—H17A | 109.0 |
O28—C3—H3A | 108.8 | C13—C18—H18A | 109.5 |
C2—C3—H3A | 108.8 | C13—C18—H18B | 109.5 |
C4—C3—H3A | 108.8 | H18A—C18—H18B | 109.5 |
C3—C4—C5 | 112.0 (2) | C13—C18—H18C | 109.5 |
C3—C4—H4A | 109.2 | H18A—C18—H18C | 109.5 |
C5—C4—H4A | 109.2 | H18B—C18—H18C | 109.5 |
C3—C4—H4B | 109.2 | C10—C19—H19A | 109.5 |
C5—C4—H4B | 109.2 | C10—C19—H19B | 109.5 |
H4A—C4—H4B | 107.9 | H19A—C19—H19B | 109.5 |
C6—C5—C4 | 120.6 (2) | C10—C19—H19C | 109.5 |
C6—C5—C10 | 122.8 (2) | H19A—C19—H19C | 109.5 |
C4—C5—C10 | 116.6 (2) | H19B—C19—H19C | 109.5 |
C5—C6—C7 | 125.9 (2) | C21—C20—C22 | 116.04 (19) |
C5—C6—H6A | 117.1 | C21—C20—C17 | 114.3 (2) |
C7—C6—H6A | 117.1 | C22—C20—C17 | 104.01 (18) |
C6—C7—C8 | 113.3 (2) | C21—C20—H20A | 107.3 |
C6—C7—H7A | 108.9 | C22—C20—H20A | 107.3 |
C8—C7—H7A | 108.9 | C17—C20—H20A | 107.3 |
C6—C7—H7B | 108.9 | C20—C21—H21A | 109.5 |
C8—C7—H7B | 108.9 | C20—C21—H21B | 109.5 |
H7A—C7—H7B | 107.7 | H21A—C21—H21B | 109.5 |
C7—C8—C14 | 110.86 (19) | C20—C21—H21C | 109.5 |
C7—C8—C9 | 110.90 (18) | H21A—C21—H21C | 109.5 |
C14—C8—C9 | 109.48 (18) | H21B—C21—H21C | 109.5 |
C7—C8—H8A | 108.5 | O22—C22—N26 | 111.7 (2) |
C14—C8—H8A | 108.5 | O22—C22—C23 | 106.4 (2) |
C9—C8—H8A | 108.5 | N26—C22—C23 | 108.20 (18) |
C11—C9—C8 | 111.30 (18) | O22—C22—C20 | 103.19 (16) |
C11—C9—C10 | 112.9 (2) | N26—C22—C20 | 111.9 (2) |
C8—C9—C10 | 113.04 (18) | C23—C22—C20 | 115.2 (2) |
C11—C9—H9A | 106.3 | C16—O22—C22 | 106.38 (18) |
C8—C9—H9A | 106.3 | C22—C23—C24 | 112.2 (2) |
C10—C9—H9A | 106.3 | C22—C23—H23A | 109.2 |
C5—C10—C1 | 109.21 (18) | C24—C23—H23A | 109.2 |
C5—C10—C19 | 108.2 (2) | C22—C23—H23B | 109.2 |
C1—C10—C19 | 109.0 (2) | C24—C23—H23B | 109.2 |
C5—C10—C9 | 109.91 (19) | H23A—C23—H23B | 107.9 |
C1—C10—C9 | 108.99 (19) | C25—C24—C23 | 111.5 (2) |
C19—C10—C9 | 111.5 (2) | C25—C24—H24A | 109.3 |
C9—C11—C12 | 113.7 (2) | C23—C24—H24A | 109.3 |
C9—C11—H11A | 108.8 | C25—C24—H24B | 109.3 |
C12—C11—H11A | 108.8 | C23—C24—H24B | 109.3 |
C9—C11—H11B | 108.8 | H24A—C24—H24B | 108.0 |
C12—C11—H11B | 108.8 | C24—C25—C26 | 109.30 (19) |
H11A—C11—H11B | 107.7 | C24—C25—C27 | 111.8 (3) |
C13—C12—C11 | 111.7 (2) | C26—C25—C27 | 110.7 (3) |
C13—C12—H12A | 109.3 | C24—C25—H25A | 108.3 |
C11—C12—H12A | 109.3 | C26—C25—H25A | 108.3 |
C13—C12—H12B | 109.3 | C27—C25—H25A | 108.3 |
C11—C12—H12B | 109.3 | N26—C26—C25 | 110.6 (2) |
H12A—C12—H12B | 107.9 | N26—C26—H26A | 109.5 |
C12—C13—C18 | 110.3 (2) | C25—C26—H26A | 109.5 |
C12—C13—C14 | 107.70 (18) | N26—C26—H26B | 109.5 |
C18—C13—C14 | 111.8 (2) | C25—C26—H26B | 109.5 |
C12—C13—C17 | 115.8 (2) | H26A—C26—H26B | 108.1 |
C18—C13—C17 | 110.8 (2) | C22—N26—C26 | 112.7 (2) |
C14—C13—C17 | 100.09 (18) | C22—N26—H26 | 108.2 |
C8—C14—C15 | 119.92 (19) | C26—N26—H26 | 111.6 |
C8—C14—C13 | 114.57 (19) | C25—C27—H27A | 109.5 |
C15—C14—C13 | 103.88 (17) | C25—C27—H27B | 109.5 |
C8—C14—H14A | 105.8 | H27A—C27—H27B | 109.5 |
C15—C14—H14A | 105.8 | C25—C27—H27C | 109.5 |
C13—C14—H14A | 105.8 | H27A—C27—H27C | 109.5 |
C16—C15—C14 | 102.15 (19) | H27B—C27—H27C | 109.5 |
C16—C15—H15A | 111.3 | C3—O28—H28 | 103.8 |
C14—C15—H15A | 111.3 | H29A—O29—H29B | 102.8 |
| | | |
C10—C1—C2—C3 | −57.7 (3) | C12—C13—C14—C15 | 168.2 (2) |
C1—C2—C3—O28 | −177.4 (2) | C18—C13—C14—C15 | −70.5 (2) |
C1—C2—C3—C4 | 60.4 (3) | C17—C13—C14—C15 | 46.8 (2) |
O28—C3—C4—C5 | −178.3 (2) | C8—C14—C15—C16 | −170.3 (2) |
C2—C3—C4—C5 | −57.0 (3) | C13—C14—C15—C16 | −40.8 (2) |
C3—C4—C5—C6 | −130.4 (3) | C14—C15—C16—O22 | 134.4 (2) |
C3—C4—C5—C10 | 50.0 (3) | C14—C15—C16—C17 | 18.4 (3) |
C4—C5—C6—C7 | −179.5 (3) | O22—C16—C17—C20 | 17.1 (3) |
C10—C5—C6—C7 | 0.1 (5) | C15—C16—C17—C20 | 137.7 (2) |
C5—C6—C7—C8 | 10.5 (4) | O22—C16—C17—C13 | −110.5 (2) |
C6—C7—C8—C14 | −159.9 (2) | C15—C16—C17—C13 | 10.0 (3) |
C6—C7—C8—C9 | −38.0 (3) | C12—C13—C17—C20 | 94.2 (3) |
C7—C8—C9—C11 | −174.3 (2) | C18—C13—C17—C20 | −32.3 (3) |
C14—C8—C9—C11 | −51.6 (3) | C14—C13—C17—C20 | −150.4 (2) |
C7—C8—C9—C10 | 57.4 (3) | C12—C13—C17—C16 | −149.4 (2) |
C14—C8—C9—C10 | −179.94 (19) | C18—C13—C17—C16 | 84.0 (2) |
C6—C5—C10—C1 | 137.0 (3) | C14—C13—C17—C16 | −34.1 (2) |
C4—C5—C10—C1 | −43.4 (3) | C16—C17—C20—C21 | 135.3 (2) |
C6—C5—C10—C19 | −104.5 (3) | C13—C17—C20—C21 | −108.3 (3) |
C4—C5—C10—C19 | 75.1 (3) | C16—C17—C20—C22 | 7.8 (2) |
C6—C5—C10—C9 | 17.5 (3) | C13—C17—C20—C22 | 124.2 (2) |
C4—C5—C10—C9 | −162.9 (2) | C21—C20—C22—O22 | −156.0 (2) |
C2—C1—C10—C5 | 47.3 (3) | C17—C20—C22—O22 | −29.6 (2) |
C2—C1—C10—C19 | −70.6 (3) | C21—C20—C22—N26 | −35.7 (3) |
C2—C1—C10—C9 | 167.4 (2) | C17—C20—C22—N26 | 90.7 (2) |
C11—C9—C10—C5 | −173.3 (2) | C21—C20—C22—C23 | 88.4 (3) |
C8—C9—C10—C5 | −45.8 (3) | C17—C20—C22—C23 | −145.2 (2) |
C11—C9—C10—C1 | 67.1 (3) | C15—C16—O22—C22 | −154.9 (2) |
C8—C9—C10—C1 | −165.5 (2) | C17—C16—O22—C22 | −37.5 (2) |
C11—C9—C10—C19 | −53.3 (3) | N26—C22—O22—C16 | −78.0 (2) |
C8—C9—C10—C19 | 74.2 (3) | C23—C22—O22—C16 | 164.1 (2) |
C8—C9—C11—C12 | 51.6 (3) | C20—C22—O22—C16 | 42.4 (2) |
C10—C9—C11—C12 | 180.0 (2) | O22—C22—C23—C24 | 64.9 (3) |
C9—C11—C12—C13 | −54.1 (3) | N26—C22—C23—C24 | −55.3 (3) |
C11—C12—C13—C18 | −67.3 (3) | C20—C22—C23—C24 | 178.6 (2) |
C11—C12—C13—C14 | 54.9 (3) | C22—C23—C24—C25 | 53.9 (3) |
C11—C12—C13—C17 | 165.9 (2) | C23—C24—C25—C26 | −52.9 (3) |
C7—C8—C14—C15 | −55.0 (3) | C23—C24—C25—C27 | −175.8 (2) |
C9—C8—C14—C15 | −177.7 (2) | C24—C25—C26—N26 | 56.1 (3) |
C7—C8—C14—C13 | −179.6 (2) | C27—C25—C26—N26 | 179.8 (2) |
C9—C8—C14—C13 | 57.8 (3) | O22—C22—N26—C26 | −57.2 (2) |
C12—C13—C14—C8 | −59.1 (3) | C23—C22—N26—C26 | 59.7 (3) |
C18—C13—C14—C8 | 62.2 (3) | C20—C22—N26—C26 | −172.32 (19) |
C17—C13—C14—C8 | 179.51 (19) | C25—C26—N26—C22 | −61.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O28—H28···O29 | 0.81 | 1.99 | 2.791 (3) | 169 |
O29—H29B···O28i | 0.86 | 2.03 | 2.861 (3) | 161 |
O29—H29A···N26ii | 0.92 | 2.05 | 2.953 (3) | 170 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1. |