The structure of the title complex, 6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3a
H-cyclopentacycloocten-8-yl [2-(diethylammonio)ethylsulfanyl]acetate (
E)-3-carboxyprop-2-enoate methanol solvate, C
28H
48NO
4S
+·C
4H
3O
4−·CH
4O, is presented. The cation of the complex consists of an eight-membered ring with boat–chair conformation, a six-membered ring with a chair conformation and a five-membered ring with a twisted conformation. The fumarate anion adopts an
E configuration. The methanol molecule is linked to the cation and the anion by O—H
O hydrogen bonds. A network of O—H
O, N—H
O and C—H
O intermolecular hydrogen bonds links the molecules, forming a layered structure.
Supporting information
CCDC reference: 231916
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.085
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C18 .. 9.36 su
Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.48 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for S - C23 .. 5.24 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C21 .. 5.01 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N - C27 .. 5.71 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C15 .. 5.47 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C20 .. 5.25 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C13
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C32
PLAT410_ALERT_2_C Short Intra H...H Contact H1 .. H5 .. 1.91 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact H2 .. H11 .. 1.94 Ang.
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 27.00
From the CIF: _reflns_number_total 7293
Count of symmetry unique reflns 4312
Completeness (_total/calc) 169.13%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2981
Fraction of Friedel pairs measured 0.691
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.
6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-
3a,9-propano-3aH-cyclopentacycloocten-8-yl
[2-(diethylammonio)ethylsulfanyl]acetate (
E)-3-carboxyprop-2-enoate
methanol solvate
top
Crystal data top
C28H48NO4S+·C4H3O4−·CH4O | F(000) = 1392 |
Mr = 641.84 | Dx = 1.218 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 39 reflections |
a = 9.935 (1) Å | θ = 3.4–14.8° |
b = 10.072 (1) Å | µ = 0.14 mm−1 |
c = 34.987 (7) Å | T = 296 K |
V = 3501.0 (8) Å3 | Block, pale-yellow |
Z = 4 | 0.56 × 0.50 × 0.44 mm |
Data collection top
Siemens P4 diffractometer | 4560 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 27.0°, θmin = 1.2° |
ω scans | h = −12→12 |
Absorption correction: ψ scan (XSCANS; Siemens, 1994) | k = −12→12 |
Tmin = 0.922, Tmax = 0.941 | l = −43→44 |
8625 measured reflections | 3 standard reflections every 97 reflections |
7293 independent reflections | intensity decay: 5.4% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.085 | (Δ/σ)max < 0.001 |
S = 0.84 | Δρmax = 0.19 e Å−3 |
7293 reflections | Δρmin = −0.12 e Å−3 |
421 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0069 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2981 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (8) |
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 | |
S | 0.87867 (8) | 0.96982 (7) | 0.055561 (18) | 0.0681 (2) | |
O1 | 0.14263 (13) | 0.66573 (17) | 0.10435 (4) | 0.0513 (4) | |
H1O | 0.1140 | 0.6660 | 0.1263 | 0.062* | |
O2 | 0.73251 (13) | 0.66680 (15) | 0.07798 (4) | 0.0442 (4) | |
O3 | 0.68992 (17) | 0.72217 (19) | 0.01662 (4) | 0.0686 (5) | |
O4 | 0.5827 (2) | 0.20171 (19) | 0.14084 (6) | 0.0853 (6) | |
O5 | 0.22235 (15) | 0.76743 (15) | 0.23423 (4) | 0.0497 (4) | |
O6 | 0.13007 (15) | 0.95231 (16) | 0.21242 (5) | 0.0622 (5) | |
O7 | 0.62163 (18) | 0.99755 (19) | 0.30143 (5) | 0.0756 (5) | |
O8 | 0.56269 (19) | 1.12903 (17) | 0.25349 (6) | 0.0751 (6) | |
H8O | 0.6335 | 1.1662 | 0.2590 | 0.090* | |
N | 0.89524 (18) | 0.94612 (18) | 0.17351 (5) | 0.0404 (4) | |
C1 | 0.29982 (19) | 0.5219 (2) | 0.06986 (5) | 0.0385 (5) | |
H1 | 0.3638 | 0.5650 | 0.0525 | 0.046* | |
C2 | 0.27900 (19) | 0.6179 (2) | 0.10414 (6) | 0.0363 (5) | |
H2 | 0.2929 | 0.5670 | 0.1277 | 0.044* | |
C3 | 0.37697 (19) | 0.73605 (19) | 0.10478 (5) | 0.0352 (5) | |
C4 | 0.5241 (2) | 0.6933 (2) | 0.11157 (6) | 0.0383 (5) | |
H4A | 0.5767 | 0.7738 | 0.1144 | 0.046* | |
H4B | 0.5267 | 0.6480 | 0.1360 | 0.046* | |
C5 | 0.59803 (19) | 0.6049 (2) | 0.08286 (6) | 0.0371 (5) | |
H5 | 0.5501 | 0.6069 | 0.0584 | 0.044* | |
C6 | 0.6203 (2) | 0.4578 (2) | 0.09508 (5) | 0.0419 (5) | |
C7 | 0.6616 (2) | 0.3672 (2) | 0.06112 (7) | 0.0546 (6) | |
H7 | 0.6705 | 0.2778 | 0.0719 | 0.065* | |
C8 | 0.5504 (3) | 0.3571 (3) | 0.03149 (7) | 0.0655 (8) | |
H8A | 0.5787 | 0.2969 | 0.0114 | 0.079* | |
H8B | 0.5365 | 0.4438 | 0.0201 | 0.079* | |
C9 | 0.4176 (3) | 0.3083 (2) | 0.04799 (7) | 0.0640 (7) | |
H9A | 0.4285 | 0.2165 | 0.0558 | 0.077* | |
H9B | 0.3501 | 0.3104 | 0.0280 | 0.077* | |
C10 | 0.3652 (2) | 0.3891 (2) | 0.08253 (6) | 0.0451 (5) | |
C11 | 0.4854 (2) | 0.4006 (2) | 0.11061 (6) | 0.0403 (5) | |
H11 | 0.4562 | 0.4616 | 0.1308 | 0.048* | |
C12 | 0.4882 (3) | 0.2625 (3) | 0.12889 (7) | 0.0592 (7) | |
C13 | 0.3464 (3) | 0.2110 (3) | 0.12973 (10) | 0.0851 (9) | |
H13A | 0.3126 | 0.2095 | 0.1557 | 0.102* | |
H13B | 0.3427 | 0.1215 | 0.1195 | 0.102* | |
C14 | 0.2633 (3) | 0.3046 (2) | 0.10530 (8) | 0.0652 (7) | |
H14A | 0.2074 | 0.3609 | 0.1213 | 0.078* | |
H14B | 0.2057 | 0.2550 | 0.0881 | 0.078* | |
C15 | 0.1705 (2) | 0.4985 (3) | 0.04691 (7) | 0.0580 (7) | |
H15A | 0.1359 | 0.5821 | 0.0381 | 0.055 (7)* | |
H15B | 0.1048 | 0.4561 | 0.0629 | 0.063 (7)* | |
H15C | 0.1898 | 0.4428 | 0.0253 | 0.084 (9)* | |
C16 | 0.3419 (2) | 0.8246 (2) | 0.13910 (6) | 0.0501 (6) | |
H16A | 0.4089 | 0.8927 | 0.1418 | 0.060* | |
H16B | 0.3395 | 0.7717 | 0.1619 | 0.060* | |
H16C | 0.2554 | 0.8648 | 0.1351 | 0.060* | |
C17 | 0.3611 (2) | 0.8172 (2) | 0.06833 (6) | 0.0460 (5) | |
H17 | 0.2807 | 0.8062 | 0.0551 | 0.055* | |
C18 | 0.4464 (3) | 0.8999 (3) | 0.05356 (8) | 0.0713 (8) | |
H18A | 0.5286 | 0.9150 | 0.0655 | 0.086* | |
H18B | 0.4255 | 0.9441 | 0.0310 | 0.086* | |
C19 | 0.7271 (2) | 0.4544 (3) | 0.12702 (6) | 0.0549 (6) | |
H19A | 0.6916 | 0.4958 | 0.1496 | 0.063 (7)* | |
H19B | 0.8060 | 0.5013 | 0.1188 | 0.074 (8)* | |
H19C | 0.7502 | 0.3639 | 0.1326 | 0.089 (9)* | |
C20 | 0.7965 (3) | 0.3972 (3) | 0.04257 (8) | 0.0880 (10) | |
H20A | 0.8279 | 0.3200 | 0.0292 | 0.106* | |
H20B | 0.8605 | 0.4213 | 0.0619 | 0.106* | |
H20C | 0.7864 | 0.4694 | 0.0249 | 0.106* | |
C21 | 0.7607 (2) | 0.7244 (2) | 0.04417 (6) | 0.0487 (6) | |
C22 | 0.8957 (2) | 0.7937 (2) | 0.04616 (6) | 0.0540 (6) | |
H22A | 0.9428 | 0.7813 | 0.0221 | 0.065* | |
H22B | 0.9494 | 0.7535 | 0.0662 | 0.065* | |
C23 | 0.8254 (2) | 0.9765 (3) | 0.10456 (6) | 0.0559 (6) | |
H23A | 0.7940 | 1.0656 | 0.1103 | 0.067* | |
H23B | 0.7504 | 0.9161 | 0.1082 | 0.067* | |
C24 | 0.9358 (2) | 0.9405 (2) | 0.13203 (6) | 0.0501 (6) | |
H24A | 1.0110 | 1.0004 | 0.1281 | 0.060* | |
H24B | 0.9666 | 0.8514 | 0.1262 | 0.060* | |
C25 | 0.8523 (3) | 1.0808 (2) | 0.18702 (7) | 0.0606 (7) | |
H25A | 0.8362 | 1.0769 | 0.2143 | 0.073* | |
H25B | 0.7678 | 1.1036 | 0.1748 | 0.073* | |
C26 | 0.9527 (3) | 1.1889 (3) | 0.17908 (9) | 0.0862 (10) | |
H26A | 1.0378 | 1.1658 | 0.1903 | 0.103* | |
H26B | 0.9213 | 1.2708 | 0.1899 | 0.103* | |
H26C | 0.9633 | 1.1992 | 0.1520 | 0.103* | |
C27 | 0.7919 (3) | 0.8430 (3) | 0.18326 (7) | 0.0634 (7) | |
H27A | 0.8095 | 0.7634 | 0.1685 | 0.076* | |
H27B | 0.7034 | 0.8755 | 0.1762 | 0.076* | |
C28 | 0.7927 (3) | 0.8088 (3) | 0.22505 (7) | 0.0796 (9) | |
H28A | 0.8801 | 0.7763 | 0.2321 | 0.096* | |
H28B | 0.7264 | 0.7417 | 0.2300 | 0.096* | |
H28C | 0.7722 | 0.8867 | 0.2398 | 0.096* | |
C29 | 0.2230 (2) | 0.8903 (2) | 0.22768 (6) | 0.0416 (5) | |
C30 | 0.3454 (2) | 0.9699 (2) | 0.23789 (6) | 0.0444 (5) | |
H30 | 0.3638 | 1.0441 | 0.2230 | 0.053* | |
C31 | 0.4283 (2) | 0.9445 (2) | 0.26577 (6) | 0.0466 (6) | |
H31 | 0.4116 | 0.8694 | 0.2805 | 0.056* | |
C32 | 0.5459 (2) | 1.0254 (2) | 0.27571 (6) | 0.0458 (5) | |
O9 | 1.05658 (17) | 0.66125 (15) | 0.17969 (4) | 0.0575 (4) | |
H9O | 1.1035 | 0.6965 | 0.1961 | 0.069* | |
C33 | 1.0254 (3) | 0.5301 (3) | 0.19100 (9) | 0.0774 (9) | |
H33A | 0.9849 | 0.4836 | 0.1700 | 0.24 (3)* | |
H33B | 0.9637 | 0.5323 | 0.2121 | 0.24 (3)* | |
H33C | 1.1064 | 0.4852 | 0.1986 | 0.170 (18)* | |
H34N | 0.9721 (16) | 0.934 (3) | 0.1849 (7) | 0.086 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0879 (5) | 0.0680 (5) | 0.0485 (3) | −0.0069 (4) | −0.0042 (4) | 0.0092 (3) |
O1 | 0.0347 (8) | 0.0649 (10) | 0.0541 (9) | 0.0145 (8) | 0.0020 (7) | 0.0036 (9) |
O2 | 0.0347 (8) | 0.0666 (10) | 0.0312 (7) | 0.0001 (8) | −0.0008 (6) | 0.0005 (7) |
O3 | 0.0632 (11) | 0.1084 (15) | 0.0341 (8) | −0.0091 (11) | −0.0076 (8) | 0.0069 (9) |
O4 | 0.0832 (14) | 0.0699 (13) | 0.1029 (15) | 0.0329 (12) | −0.0087 (12) | 0.0286 (11) |
O5 | 0.0417 (9) | 0.0455 (10) | 0.0620 (10) | 0.0006 (8) | −0.0086 (8) | 0.0017 (8) |
O6 | 0.0457 (9) | 0.0509 (10) | 0.0901 (12) | 0.0105 (9) | −0.0301 (9) | −0.0082 (9) |
O7 | 0.0710 (12) | 0.0991 (14) | 0.0568 (10) | −0.0221 (12) | −0.0268 (10) | 0.0084 (10) |
O8 | 0.0681 (13) | 0.0618 (12) | 0.0955 (14) | −0.0194 (10) | −0.0415 (11) | 0.0159 (11) |
N | 0.0330 (10) | 0.0445 (11) | 0.0437 (10) | 0.0000 (9) | −0.0074 (9) | −0.0029 (9) |
C1 | 0.0312 (11) | 0.0428 (12) | 0.0416 (11) | 0.0000 (10) | −0.0066 (9) | −0.0035 (10) |
C2 | 0.0299 (11) | 0.0433 (12) | 0.0358 (11) | 0.0087 (10) | −0.0028 (10) | 0.0050 (10) |
C3 | 0.0361 (11) | 0.0360 (11) | 0.0334 (10) | 0.0064 (10) | 0.0001 (10) | −0.0005 (9) |
C4 | 0.0402 (12) | 0.0421 (13) | 0.0326 (11) | 0.0003 (10) | −0.0028 (10) | 0.0011 (10) |
C5 | 0.0294 (11) | 0.0496 (13) | 0.0321 (10) | 0.0028 (10) | −0.0074 (9) | −0.0055 (10) |
C6 | 0.0390 (12) | 0.0482 (13) | 0.0385 (11) | 0.0127 (12) | −0.0033 (10) | −0.0039 (11) |
C7 | 0.0542 (14) | 0.0548 (16) | 0.0547 (14) | 0.0205 (12) | 0.0068 (12) | −0.0101 (12) |
C8 | 0.0790 (19) | 0.0656 (18) | 0.0519 (14) | 0.0235 (16) | −0.0008 (14) | −0.0252 (13) |
C9 | 0.0703 (17) | 0.0517 (15) | 0.0701 (17) | 0.0111 (14) | −0.0182 (15) | −0.0223 (13) |
C10 | 0.0435 (13) | 0.0384 (12) | 0.0533 (13) | 0.0058 (12) | −0.0059 (11) | −0.0079 (11) |
C11 | 0.0477 (13) | 0.0341 (12) | 0.0393 (12) | 0.0121 (10) | −0.0005 (11) | −0.0033 (10) |
C12 | 0.0683 (18) | 0.0467 (15) | 0.0626 (16) | 0.0207 (14) | 0.0011 (14) | 0.0058 (13) |
C13 | 0.075 (2) | 0.0508 (17) | 0.130 (3) | 0.0050 (16) | −0.0037 (19) | 0.0299 (18) |
C14 | 0.0569 (16) | 0.0460 (15) | 0.0928 (19) | −0.0055 (13) | −0.0041 (16) | 0.0067 (15) |
C15 | 0.0486 (14) | 0.0661 (19) | 0.0592 (16) | −0.0019 (13) | −0.0136 (12) | −0.0036 (14) |
C16 | 0.0533 (14) | 0.0425 (13) | 0.0543 (13) | 0.0077 (12) | 0.0049 (12) | −0.0077 (11) |
C17 | 0.0453 (13) | 0.0459 (13) | 0.0468 (12) | 0.0055 (12) | −0.0051 (11) | 0.0061 (11) |
C18 | 0.0826 (19) | 0.0653 (18) | 0.0659 (17) | 0.0014 (17) | −0.0118 (16) | 0.0187 (15) |
C19 | 0.0496 (15) | 0.0610 (17) | 0.0542 (14) | 0.0161 (14) | −0.0113 (12) | 0.0040 (14) |
C20 | 0.076 (2) | 0.098 (2) | 0.090 (2) | 0.0174 (18) | 0.0275 (18) | −0.0378 (18) |
C21 | 0.0461 (14) | 0.0624 (16) | 0.0377 (12) | 0.0099 (12) | 0.0055 (11) | −0.0018 (12) |
C22 | 0.0477 (14) | 0.0704 (17) | 0.0440 (13) | 0.0004 (13) | 0.0124 (11) | 0.0021 (12) |
C23 | 0.0544 (14) | 0.0569 (15) | 0.0565 (14) | 0.0097 (13) | −0.0129 (12) | −0.0053 (13) |
C24 | 0.0451 (13) | 0.0537 (15) | 0.0515 (13) | 0.0093 (12) | −0.0016 (11) | −0.0001 (11) |
C25 | 0.0621 (17) | 0.0516 (15) | 0.0682 (16) | 0.0173 (13) | −0.0139 (14) | −0.0101 (13) |
C26 | 0.102 (2) | 0.0452 (16) | 0.111 (2) | −0.0008 (18) | −0.034 (2) | 0.0018 (17) |
C27 | 0.0581 (16) | 0.0661 (17) | 0.0658 (16) | −0.0126 (14) | −0.0072 (14) | −0.0016 (14) |
C28 | 0.084 (2) | 0.084 (2) | 0.0710 (18) | −0.0157 (19) | 0.0160 (16) | 0.0086 (16) |
C29 | 0.0366 (12) | 0.0479 (14) | 0.0404 (12) | 0.0050 (12) | −0.0048 (10) | −0.0116 (11) |
C30 | 0.0409 (12) | 0.0445 (13) | 0.0478 (12) | 0.0034 (11) | −0.0053 (10) | −0.0046 (11) |
C31 | 0.0481 (13) | 0.0466 (13) | 0.0450 (12) | −0.0012 (12) | −0.0045 (11) | −0.0039 (11) |
C32 | 0.0426 (13) | 0.0512 (15) | 0.0436 (12) | −0.0008 (12) | −0.0028 (11) | −0.0099 (12) |
O9 | 0.0585 (11) | 0.0555 (10) | 0.0583 (10) | −0.0132 (9) | −0.0082 (8) | 0.0019 (9) |
C33 | 0.088 (2) | 0.0576 (18) | 0.087 (2) | −0.0188 (18) | −0.0244 (19) | 0.0104 (17) |
Geometric parameters (Å, º) top
S—C23 | 1.796 (2) | C13—H13B | 0.97 |
S—C22 | 1.812 (3) | C14—H14A | 0.97 |
O1—C2 | 1.438 (2) | C14—H14B | 0.97 |
O1—H1O | 0.82 | C15—H15A | 0.96 |
O2—C21 | 1.347 (2) | C15—H15B | 0.96 |
O2—C5 | 1.484 (2) | C15—H15C | 0.96 |
O3—C21 | 1.193 (3) | C16—H16A | 0.96 |
O4—C12 | 1.196 (3) | C16—H16B | 0.96 |
O5—C29 | 1.259 (2) | C16—H16C | 0.96 |
O6—C29 | 1.236 (2) | C17—C18 | 1.296 (3) |
O7—C32 | 1.206 (2) | C17—H17 | 0.93 |
O8—C32 | 1.312 (3) | C18—H18A | 0.93 |
O8—H8O | 0.82 | C18—H18B | 0.93 |
N—C25 | 1.499 (3) | C19—H19A | 0.96 |
N—C27 | 1.500 (3) | C19—H19B | 0.96 |
N—C24 | 1.507 (3) | C19—H19C | 0.96 |
N—H34N | 0.87 (1) | C20—H20A | 0.96 |
C1—C15 | 1.533 (3) | C20—H20B | 0.96 |
C1—C10 | 1.551 (3) | C20—H20C | 0.96 |
C1—C2 | 1.555 (3) | C21—C22 | 1.513 (3) |
C1—H1 | 0.98 | C22—H22A | 0.97 |
C2—C3 | 1.537 (3) | C22—H22B | 0.97 |
C2—H2 | 0.98 | C23—C24 | 1.503 (3) |
C3—C17 | 1.523 (3) | C23—H23A | 0.97 |
C3—C16 | 1.536 (3) | C23—H23B | 0.97 |
C3—C4 | 1.542 (3) | C24—H24A | 0.97 |
C4—C5 | 1.530 (3) | C24—H24B | 0.97 |
C4—H4A | 0.97 | C25—C26 | 1.503 (4) |
C4—H4B | 0.97 | C25—H25A | 0.97 |
C5—C6 | 1.558 (3) | C25—H25B | 0.97 |
C5—H5 | 0.98 | C26—H26A | 0.96 |
C6—C19 | 1.541 (3) | C26—H26B | 0.96 |
C6—C7 | 1.554 (3) | C26—H26C | 0.96 |
C6—C11 | 1.557 (3) | C27—C28 | 1.502 (3) |
C7—C8 | 1.519 (3) | C27—H27A | 0.97 |
C7—C20 | 1.520 (3) | C27—H27B | 0.97 |
C7—H7 | 0.98 | C28—H28A | 0.96 |
C8—C9 | 1.521 (4) | C28—H28B | 0.96 |
C8—H8A | 0.97 | C28—H28C | 0.96 |
C8—H8B | 0.97 | C29—C30 | 1.500 (3) |
C9—C10 | 1.548 (3) | C30—C31 | 1.302 (3) |
C9—H9A | 0.97 | C30—H30 | 0.93 |
C9—H9B | 0.97 | C31—C32 | 1.467 (3) |
C10—C14 | 1.544 (3) | C31—H31 | 0.93 |
C10—C11 | 1.551 (3) | O9—C33 | 1.413 (3) |
C11—C12 | 1.532 (3) | O9—H9O | 0.82 |
C11—H11 | 0.98 | C33—H33A | 0.96 |
C12—C13 | 1.502 (4) | C33—H33B | 0.96 |
C13—C14 | 1.517 (3) | C33—H33C | 0.96 |
C13—H13A | 0.97 | | |
| | | |
C23—S—C22 | 103.75 (12) | H15A—C15—H15B | 109.5 |
C2—O1—H1O | 109.5 | C1—C15—H15C | 109.5 |
C21—O2—C5 | 117.98 (16) | H15A—C15—H15C | 109.5 |
C32—O8—H8O | 109.5 | H15B—C15—H15C | 109.5 |
C25—N—C27 | 111.12 (18) | C3—C16—H16A | 109.5 |
C25—N—C24 | 114.44 (18) | C3—C16—H16B | 109.5 |
C27—N—C24 | 112.08 (17) | H16A—C16—H16B | 109.5 |
C25—N—H34N | 103.6 (19) | C3—C16—H16C | 109.5 |
C27—N—H34N | 113.3 (19) | H16A—C16—H16C | 109.5 |
C24—N—H34N | 101.6 (18) | H16B—C16—H16C | 109.5 |
C15—C1—C10 | 111.62 (18) | C18—C17—C3 | 127.7 (2) |
C15—C1—C2 | 112.81 (17) | C18—C17—H17 | 116.2 |
C10—C1—C2 | 111.82 (16) | C3—C17—H17 | 116.2 |
C15—C1—H1 | 106.7 | C17—C18—H18A | 120.0 |
C10—C1—H1 | 106.7 | C17—C18—H18B | 120.0 |
C2—C1—H1 | 106.7 | H18A—C18—H18B | 120.0 |
O1—C2—C3 | 109.72 (16) | C6—C19—H19A | 109.5 |
O1—C2—C1 | 109.74 (16) | C6—C19—H19B | 109.5 |
C3—C2—C1 | 114.12 (16) | H19A—C19—H19B | 109.5 |
O1—C2—H2 | 107.7 | C6—C19—H19C | 109.5 |
C3—C2—H2 | 107.7 | H19A—C19—H19C | 109.5 |
C1—C2—H2 | 107.7 | H19B—C19—H19C | 109.5 |
C17—C3—C16 | 108.62 (16) | C7—C20—H20A | 109.5 |
C17—C3—C2 | 109.73 (16) | C7—C20—H20B | 109.5 |
C16—C3—C2 | 108.50 (16) | H20A—C20—H20B | 109.5 |
C17—C3—C4 | 112.16 (17) | C7—C20—H20C | 109.5 |
C16—C3—C4 | 104.89 (16) | H20A—C20—H20C | 109.5 |
C2—C3—C4 | 112.70 (16) | H20B—C20—H20C | 109.5 |
C5—C4—C3 | 121.10 (16) | O3—C21—O2 | 125.4 (2) |
C5—C4—H4A | 107.1 | O3—C21—C22 | 124.6 (2) |
C3—C4—H4A | 107.1 | O2—C21—C22 | 110.04 (19) |
C5—C4—H4B | 107.1 | C21—C22—S | 112.18 (16) |
C3—C4—H4B | 107.1 | C21—C22—H22A | 109.2 |
H4A—C4—H4B | 106.8 | S—C22—H22A | 109.2 |
O2—C5—C4 | 105.28 (15) | C21—C22—H22B | 109.2 |
O2—C5—C6 | 107.65 (16) | S—C22—H22B | 109.2 |
C4—C5—C6 | 116.17 (17) | H22A—C22—H22B | 107.9 |
O2—C5—H5 | 109.2 | C24—C23—S | 112.72 (16) |
C4—C5—H5 | 109.2 | C24—C23—H23A | 109.0 |
C6—C5—H5 | 109.2 | S—C23—H23A | 109.0 |
C19—C6—C7 | 111.08 (17) | C24—C23—H23B | 109.0 |
C19—C6—C11 | 109.34 (17) | S—C23—H23B | 109.0 |
C7—C6—C11 | 106.06 (18) | H23A—C23—H23B | 107.8 |
C19—C6—C5 | 108.56 (18) | C23—C24—N | 114.30 (18) |
C7—C6—C5 | 112.74 (17) | C23—C24—H24A | 108.7 |
C11—C6—C5 | 108.99 (16) | N—C24—H24A | 108.7 |
C8—C7—C20 | 111.3 (2) | C23—C24—H24B | 108.7 |
C8—C7—C6 | 111.67 (17) | N—C24—H24B | 108.7 |
C20—C7—C6 | 116.3 (2) | H24A—C24—H24B | 107.6 |
C8—C7—H7 | 105.6 | N—C25—C26 | 114.1 (2) |
C20—C7—H7 | 105.6 | N—C25—H25A | 108.7 |
C6—C7—H7 | 105.6 | C26—C25—H25A | 108.7 |
C7—C8—C9 | 113.1 (2) | N—C25—H25B | 108.7 |
C7—C8—H8A | 109.0 | C26—C25—H25B | 108.7 |
C9—C8—H8A | 109.0 | H25A—C25—H25B | 107.6 |
C7—C8—H8B | 109.0 | C25—C26—H26A | 109.5 |
C9—C8—H8B | 109.0 | C25—C26—H26B | 109.5 |
H8A—C8—H8B | 107.8 | H26A—C26—H26B | 109.5 |
C8—C9—C10 | 114.7 (2) | C25—C26—H26C | 109.5 |
C8—C9—H9A | 108.6 | H26A—C26—H26C | 109.5 |
C10—C9—H9A | 108.6 | H26B—C26—H26C | 109.5 |
C8—C9—H9B | 108.6 | N—C27—C28 | 112.1 (2) |
C10—C9—H9B | 108.6 | N—C27—H27A | 109.2 |
H9A—C9—H9B | 107.6 | C28—C27—H27A | 109.2 |
C14—C10—C9 | 109.5 (2) | N—C27—H27B | 109.2 |
C14—C10—C1 | 110.39 (18) | C28—C27—H27B | 109.2 |
C9—C10—C1 | 111.81 (18) | H27A—C27—H27B | 107.9 |
C14—C10—C11 | 102.64 (18) | C27—C28—H28A | 109.5 |
C9—C10—C11 | 105.92 (17) | C27—C28—H28B | 109.5 |
C1—C10—C11 | 116.05 (17) | H28A—C28—H28B | 109.5 |
C12—C11—C10 | 102.18 (19) | C27—C28—H28C | 109.5 |
C12—C11—C6 | 117.78 (18) | H28A—C28—H28C | 109.5 |
C10—C11—C6 | 118.00 (17) | H28B—C28—H28C | 109.5 |
C12—C11—H11 | 105.9 | O6—C29—O5 | 124.9 (2) |
C10—C11—H11 | 105.9 | O6—C29—C30 | 116.0 (2) |
C6—C11—H11 | 105.9 | O5—C29—C30 | 119.1 (2) |
O4—C12—C13 | 123.6 (2) | C31—C30—C29 | 125.9 (2) |
O4—C12—C11 | 128.7 (3) | C31—C30—H30 | 117.1 |
C13—C12—C11 | 107.7 (2) | C29—C30—H30 | 117.1 |
C12—C13—C14 | 106.5 (2) | C30—C31—C32 | 124.9 (2) |
C12—C13—H13A | 110.4 | C30—C31—H31 | 117.5 |
C14—C13—H13A | 110.4 | C32—C31—H31 | 117.5 |
C12—C13—H13B | 110.4 | O7—C32—O8 | 123.2 (2) |
C14—C13—H13B | 110.4 | O7—C32—C31 | 123.0 (2) |
H13A—C13—H13B | 108.6 | O8—C32—C31 | 113.7 (2) |
C13—C14—C10 | 106.1 (2) | C33—O9—H9O | 109.5 |
C13—C14—H14A | 110.5 | O9—C33—H33A | 109.5 |
C10—C14—H14A | 110.5 | O9—C33—H33B | 109.5 |
C13—C14—H14B | 110.5 | H33A—C33—H33B | 109.5 |
C10—C14—H14B | 110.5 | O9—C33—H33C | 109.5 |
H14A—C14—H14B | 108.7 | H33A—C33—H33C | 109.5 |
C1—C15—H15A | 109.5 | H33B—C33—H33C | 109.5 |
C1—C15—H15B | 109.5 | | |
| | | |
C15—C1—C2—O1 | −2.7 (2) | C9—C10—C11—C12 | −76.7 (2) |
C10—C1—C2—O1 | −129.52 (17) | C1—C10—C11—C12 | 158.58 (19) |
C15—C1—C2—C3 | −126.3 (2) | C14—C10—C11—C6 | 169.01 (18) |
C10—C1—C2—C3 | 106.88 (19) | C9—C10—C11—C6 | 54.2 (2) |
O1—C2—C3—C17 | −64.1 (2) | C1—C10—C11—C6 | −70.5 (2) |
C1—C2—C3—C17 | 59.5 (2) | C19—C6—C11—C12 | −54.0 (3) |
O1—C2—C3—C16 | 54.4 (2) | C7—C6—C11—C12 | 65.8 (2) |
C1—C2—C3—C16 | 178.04 (17) | C5—C6—C11—C12 | −172.57 (18) |
O1—C2—C3—C4 | 170.12 (15) | C19—C6—C11—C10 | −177.43 (18) |
C1—C2—C3—C4 | −66.3 (2) | C7—C6—C11—C10 | −57.6 (2) |
C17—C3—C4—C5 | −61.1 (3) | C5—C6—C11—C10 | 64.0 (2) |
C16—C3—C4—C5 | −178.85 (19) | C10—C11—C12—O4 | 149.3 (3) |
C2—C3—C4—C5 | 63.3 (2) | C6—C11—C12—O4 | 18.3 (4) |
C21—O2—C5—C4 | −110.79 (19) | C10—C11—C12—C13 | −30.7 (3) |
C21—O2—C5—C6 | 124.69 (18) | C6—C11—C12—C13 | −161.8 (2) |
C3—C4—C5—O2 | 134.78 (18) | O4—C12—C13—C14 | −169.2 (3) |
C3—C4—C5—C6 | −106.2 (2) | C11—C12—C13—C14 | 10.8 (3) |
O2—C5—C6—C19 | 46.4 (2) | C12—C13—C14—C10 | 13.9 (3) |
C4—C5—C6—C19 | −71.3 (2) | C9—C10—C14—C13 | 79.6 (3) |
O2—C5—C6—C7 | −77.13 (19) | C1—C10—C14—C13 | −156.9 (2) |
C4—C5—C6—C7 | 165.20 (17) | C11—C10—C14—C13 | −32.6 (3) |
O2—C5—C6—C11 | 165.39 (15) | C16—C3—C17—C18 | 81.7 (3) |
C4—C5—C6—C11 | 47.7 (2) | C2—C3—C17—C18 | −159.8 (2) |
C19—C6—C7—C8 | 173.5 (2) | C4—C3—C17—C18 | −33.8 (3) |
C11—C6—C7—C8 | 54.8 (2) | C5—O2—C21—O3 | −5.5 (3) |
C5—C6—C7—C8 | −64.4 (3) | C5—O2—C21—C22 | 174.15 (17) |
C19—C6—C7—C20 | −57.3 (3) | O3—C21—C22—S | 82.1 (3) |
C11—C6—C7—C20 | −176.0 (2) | O2—C21—C22—S | −97.49 (19) |
C5—C6—C7—C20 | 64.8 (3) | C23—S—C22—C21 | 71.21 (18) |
C20—C7—C8—C9 | 172.0 (2) | C22—S—C23—C24 | 71.8 (2) |
C6—C7—C8—C9 | −56.3 (3) | S—C23—C24—N | 179.51 (16) |
C7—C8—C9—C10 | 54.3 (3) | C25—N—C24—C23 | −61.6 (3) |
C8—C9—C10—C14 | −159.6 (2) | C27—N—C24—C23 | 66.1 (3) |
C8—C9—C10—C1 | 77.7 (2) | C27—N—C25—C26 | 178.6 (2) |
C8—C9—C10—C11 | −49.6 (3) | C24—N—C25—C26 | −53.2 (3) |
C15—C1—C10—C14 | −55.6 (2) | C25—N—C27—C28 | −74.3 (3) |
C2—C1—C10—C14 | 71.8 (2) | C24—N—C27—C28 | 156.2 (2) |
C15—C1—C10—C9 | 66.5 (2) | O6—C29—C30—C31 | 151.2 (2) |
C2—C1—C10—C9 | −166.05 (18) | O5—C29—C30—C31 | −30.2 (3) |
C15—C1—C10—C11 | −171.85 (18) | C29—C30—C31—C32 | −178.68 (19) |
C2—C1—C10—C11 | −44.4 (2) | C30—C31—C32—O7 | −178.9 (2) |
C14—C10—C11—C12 | 38.1 (2) | C30—C31—C32—O8 | −0.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O9i | 0.82 | 1.95 | 2.772 (2) | 176 |
O8—H8O···O5ii | 0.82 | 1.77 | 2.586 (2) | 171 |
O9—H9O···O5iii | 0.82 | 1.92 | 2.738 (2) | 176 |
N—H34N···O6iii | 0.87 (1) | 1.85 (1) | 2.702 (2) | 165 (3) |
C5—H5···O3 | 0.98 | 2.33 | 2.757 (3) | 106 |
C11—H11···O7iv | 0.98 | 2.52 | 3.399 (3) | 149 |
C19—H19B···O2 | 0.96 | 2.31 | 2.743 (3) | 106 |
C19—H19C···O4 | 0.96 | 2.35 | 2.961 (3) | 121 |
C22—H22B···O1iii | 0.97 | 2.50 | 3.439 (3) | 163 |
C25—H25B···O4v | 0.97 | 2.40 | 3.357 (3) | 168 |
C26—H26A···O6iii | 0.96 | 2.46 | 3.185 (3) | 132 |
C30—H30···O8 | 0.93 | 2.40 | 2.744 (3) | 101 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1, y−1/2, −z+1/2; (v) x, y+1, z. |