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The structure of the title complex, 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, C28H48NO4S+·C4H3O4·CH4O, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019713/ci6411sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019713/ci6411Isup2.hkl
Contains datablock I

CCDC reference: 231916

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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·CH4OF(000) = 1392
Mr = 641.84Dx = 1.218 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 39 reflections
a = 9.935 (1) Åθ = 3.4–14.8°
b = 10.072 (1) ŵ = 0.14 mm1
c = 34.987 (7) ÅT = 296 K
V = 3501.0 (8) Å3Block, pale-yellow
Z = 40.56 × 0.50 × 0.44 mm
Data collection top
Siemens P4
diffractometer
4560 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 27.0°, θmin = 1.2°
ω scansh = 1212
Absorption correction: ψ scan
(XSCANS; Siemens, 1994)
k = 1212
Tmin = 0.922, Tmax = 0.941l = 4344
8625 measured reflections3 standard reflections every 97 reflections
7293 independent reflections intensity decay: 5.4%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 0.84Δρmax = 0.19 e Å3
7293 reflectionsΔρmin = 0.12 e Å3
421 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0069 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2981 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute 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
xyzUiso*/Ueq
S0.87867 (8)0.96982 (7)0.055561 (18)0.0681 (2)
O10.14263 (13)0.66573 (17)0.10435 (4)0.0513 (4)
H1O0.11400.66600.12630.062*
O20.73251 (13)0.66680 (15)0.07798 (4)0.0442 (4)
O30.68992 (17)0.72217 (19)0.01662 (4)0.0686 (5)
O40.5827 (2)0.20171 (19)0.14084 (6)0.0853 (6)
O50.22235 (15)0.76743 (15)0.23423 (4)0.0497 (4)
O60.13007 (15)0.95231 (16)0.21242 (5)0.0622 (5)
O70.62163 (18)0.99755 (19)0.30143 (5)0.0756 (5)
O80.56269 (19)1.12903 (17)0.25349 (6)0.0751 (6)
H8O0.63351.16620.25900.090*
N0.89524 (18)0.94612 (18)0.17351 (5)0.0404 (4)
C10.29982 (19)0.5219 (2)0.06986 (5)0.0385 (5)
H10.36380.56500.05250.046*
C20.27900 (19)0.6179 (2)0.10414 (6)0.0363 (5)
H20.29290.56700.12770.044*
C30.37697 (19)0.73605 (19)0.10478 (5)0.0352 (5)
C40.5241 (2)0.6933 (2)0.11157 (6)0.0383 (5)
H4A0.57670.77380.11440.046*
H4B0.52670.64800.13600.046*
C50.59803 (19)0.6049 (2)0.08286 (6)0.0371 (5)
H50.55010.60690.05840.044*
C60.6203 (2)0.4578 (2)0.09508 (5)0.0419 (5)
C70.6616 (2)0.3672 (2)0.06112 (7)0.0546 (6)
H70.67050.27780.07190.065*
C80.5504 (3)0.3571 (3)0.03149 (7)0.0655 (8)
H8A0.57870.29690.01140.079*
H8B0.53650.44380.02010.079*
C90.4176 (3)0.3083 (2)0.04799 (7)0.0640 (7)
H9A0.42850.21650.05580.077*
H9B0.35010.31040.02800.077*
C100.3652 (2)0.3891 (2)0.08253 (6)0.0451 (5)
C110.4854 (2)0.4006 (2)0.11061 (6)0.0403 (5)
H110.45620.46160.13080.048*
C120.4882 (3)0.2625 (3)0.12889 (7)0.0592 (7)
C130.3464 (3)0.2110 (3)0.12973 (10)0.0851 (9)
H13A0.31260.20950.15570.102*
H13B0.34270.12150.11950.102*
C140.2633 (3)0.3046 (2)0.10530 (8)0.0652 (7)
H14A0.20740.36090.12130.078*
H14B0.20570.25500.08810.078*
C150.1705 (2)0.4985 (3)0.04691 (7)0.0580 (7)
H15A0.13590.58210.03810.055 (7)*
H15B0.10480.45610.06290.063 (7)*
H15C0.18980.44280.02530.084 (9)*
C160.3419 (2)0.8246 (2)0.13910 (6)0.0501 (6)
H16A0.40890.89270.14180.060*
H16B0.33950.77170.16190.060*
H16C0.25540.86480.13510.060*
C170.3611 (2)0.8172 (2)0.06833 (6)0.0460 (5)
H170.28070.80620.05510.055*
C180.4464 (3)0.8999 (3)0.05356 (8)0.0713 (8)
H18A0.52860.91500.06550.086*
H18B0.42550.94410.03100.086*
C190.7271 (2)0.4544 (3)0.12702 (6)0.0549 (6)
H19A0.69160.49580.14960.063 (7)*
H19B0.80600.50130.11880.074 (8)*
H19C0.75020.36390.13260.089 (9)*
C200.7965 (3)0.3972 (3)0.04257 (8)0.0880 (10)
H20A0.82790.32000.02920.106*
H20B0.86050.42130.06190.106*
H20C0.78640.46940.02490.106*
C210.7607 (2)0.7244 (2)0.04417 (6)0.0487 (6)
C220.8957 (2)0.7937 (2)0.04616 (6)0.0540 (6)
H22A0.94280.78130.02210.065*
H22B0.94940.75350.06620.065*
C230.8254 (2)0.9765 (3)0.10456 (6)0.0559 (6)
H23A0.79401.06560.11030.067*
H23B0.75040.91610.10820.067*
C240.9358 (2)0.9405 (2)0.13203 (6)0.0501 (6)
H24A1.01101.00040.12810.060*
H24B0.96660.85140.12620.060*
C250.8523 (3)1.0808 (2)0.18702 (7)0.0606 (7)
H25A0.83621.07690.21430.073*
H25B0.76781.10360.17480.073*
C260.9527 (3)1.1889 (3)0.17908 (9)0.0862 (10)
H26A1.03781.16580.19030.103*
H26B0.92131.27080.18990.103*
H26C0.96331.19920.15200.103*
C270.7919 (3)0.8430 (3)0.18326 (7)0.0634 (7)
H27A0.80950.76340.16850.076*
H27B0.70340.87550.17620.076*
C280.7927 (3)0.8088 (3)0.22505 (7)0.0796 (9)
H28A0.88010.77630.23210.096*
H28B0.72640.74170.23000.096*
H28C0.77220.88670.23980.096*
C290.2230 (2)0.8903 (2)0.22768 (6)0.0416 (5)
C300.3454 (2)0.9699 (2)0.23789 (6)0.0444 (5)
H300.36381.04410.22300.053*
C310.4283 (2)0.9445 (2)0.26577 (6)0.0466 (6)
H310.41160.86940.28050.056*
C320.5459 (2)1.0254 (2)0.27571 (6)0.0458 (5)
O91.05658 (17)0.66125 (15)0.17969 (4)0.0575 (4)
H9O1.10350.69650.19610.069*
C331.0254 (3)0.5301 (3)0.19100 (9)0.0774 (9)
H33A0.98490.48360.17000.24 (3)*
H33B0.96370.53230.21210.24 (3)*
H33C1.10640.48520.19860.170 (18)*
H34N0.9721 (16)0.934 (3)0.1849 (7)0.086 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0879 (5)0.0680 (5)0.0485 (3)0.0069 (4)0.0042 (4)0.0092 (3)
O10.0347 (8)0.0649 (10)0.0541 (9)0.0145 (8)0.0020 (7)0.0036 (9)
O20.0347 (8)0.0666 (10)0.0312 (7)0.0001 (8)0.0008 (6)0.0005 (7)
O30.0632 (11)0.1084 (15)0.0341 (8)0.0091 (11)0.0076 (8)0.0069 (9)
O40.0832 (14)0.0699 (13)0.1029 (15)0.0329 (12)0.0087 (12)0.0286 (11)
O50.0417 (9)0.0455 (10)0.0620 (10)0.0006 (8)0.0086 (8)0.0017 (8)
O60.0457 (9)0.0509 (10)0.0901 (12)0.0105 (9)0.0301 (9)0.0082 (9)
O70.0710 (12)0.0991 (14)0.0568 (10)0.0221 (12)0.0268 (10)0.0084 (10)
O80.0681 (13)0.0618 (12)0.0955 (14)0.0194 (10)0.0415 (11)0.0159 (11)
N0.0330 (10)0.0445 (11)0.0437 (10)0.0000 (9)0.0074 (9)0.0029 (9)
C10.0312 (11)0.0428 (12)0.0416 (11)0.0000 (10)0.0066 (9)0.0035 (10)
C20.0299 (11)0.0433 (12)0.0358 (11)0.0087 (10)0.0028 (10)0.0050 (10)
C30.0361 (11)0.0360 (11)0.0334 (10)0.0064 (10)0.0001 (10)0.0005 (9)
C40.0402 (12)0.0421 (13)0.0326 (11)0.0003 (10)0.0028 (10)0.0011 (10)
C50.0294 (11)0.0496 (13)0.0321 (10)0.0028 (10)0.0074 (9)0.0055 (10)
C60.0390 (12)0.0482 (13)0.0385 (11)0.0127 (12)0.0033 (10)0.0039 (11)
C70.0542 (14)0.0548 (16)0.0547 (14)0.0205 (12)0.0068 (12)0.0101 (12)
C80.0790 (19)0.0656 (18)0.0519 (14)0.0235 (16)0.0008 (14)0.0252 (13)
C90.0703 (17)0.0517 (15)0.0701 (17)0.0111 (14)0.0182 (15)0.0223 (13)
C100.0435 (13)0.0384 (12)0.0533 (13)0.0058 (12)0.0059 (11)0.0079 (11)
C110.0477 (13)0.0341 (12)0.0393 (12)0.0121 (10)0.0005 (11)0.0033 (10)
C120.0683 (18)0.0467 (15)0.0626 (16)0.0207 (14)0.0011 (14)0.0058 (13)
C130.075 (2)0.0508 (17)0.130 (3)0.0050 (16)0.0037 (19)0.0299 (18)
C140.0569 (16)0.0460 (15)0.0928 (19)0.0055 (13)0.0041 (16)0.0067 (15)
C150.0486 (14)0.0661 (19)0.0592 (16)0.0019 (13)0.0136 (12)0.0036 (14)
C160.0533 (14)0.0425 (13)0.0543 (13)0.0077 (12)0.0049 (12)0.0077 (11)
C170.0453 (13)0.0459 (13)0.0468 (12)0.0055 (12)0.0051 (11)0.0061 (11)
C180.0826 (19)0.0653 (18)0.0659 (17)0.0014 (17)0.0118 (16)0.0187 (15)
C190.0496 (15)0.0610 (17)0.0542 (14)0.0161 (14)0.0113 (12)0.0040 (14)
C200.076 (2)0.098 (2)0.090 (2)0.0174 (18)0.0275 (18)0.0378 (18)
C210.0461 (14)0.0624 (16)0.0377 (12)0.0099 (12)0.0055 (11)0.0018 (12)
C220.0477 (14)0.0704 (17)0.0440 (13)0.0004 (13)0.0124 (11)0.0021 (12)
C230.0544 (14)0.0569 (15)0.0565 (14)0.0097 (13)0.0129 (12)0.0053 (13)
C240.0451 (13)0.0537 (15)0.0515 (13)0.0093 (12)0.0016 (11)0.0001 (11)
C250.0621 (17)0.0516 (15)0.0682 (16)0.0173 (13)0.0139 (14)0.0101 (13)
C260.102 (2)0.0452 (16)0.111 (2)0.0008 (18)0.034 (2)0.0018 (17)
C270.0581 (16)0.0661 (17)0.0658 (16)0.0126 (14)0.0072 (14)0.0016 (14)
C280.084 (2)0.084 (2)0.0710 (18)0.0157 (19)0.0160 (16)0.0086 (16)
C290.0366 (12)0.0479 (14)0.0404 (12)0.0050 (12)0.0048 (10)0.0116 (11)
C300.0409 (12)0.0445 (13)0.0478 (12)0.0034 (11)0.0053 (10)0.0046 (11)
C310.0481 (13)0.0466 (13)0.0450 (12)0.0012 (12)0.0045 (11)0.0039 (11)
C320.0426 (13)0.0512 (15)0.0436 (12)0.0008 (12)0.0028 (11)0.0099 (12)
O90.0585 (11)0.0555 (10)0.0583 (10)0.0132 (9)0.0082 (8)0.0019 (9)
C330.088 (2)0.0576 (18)0.087 (2)0.0188 (18)0.0244 (19)0.0104 (17)
Geometric parameters (Å, º) top
S—C231.796 (2)C13—H13B0.97
S—C221.812 (3)C14—H14A0.97
O1—C21.438 (2)C14—H14B0.97
O1—H1O0.82C15—H15A0.96
O2—C211.347 (2)C15—H15B0.96
O2—C51.484 (2)C15—H15C0.96
O3—C211.193 (3)C16—H16A0.96
O4—C121.196 (3)C16—H16B0.96
O5—C291.259 (2)C16—H16C0.96
O6—C291.236 (2)C17—C181.296 (3)
O7—C321.206 (2)C17—H170.93
O8—C321.312 (3)C18—H18A0.93
O8—H8O0.82C18—H18B0.93
N—C251.499 (3)C19—H19A0.96
N—C271.500 (3)C19—H19B0.96
N—C241.507 (3)C19—H19C0.96
N—H34N0.87 (1)C20—H20A0.96
C1—C151.533 (3)C20—H20B0.96
C1—C101.551 (3)C20—H20C0.96
C1—C21.555 (3)C21—C221.513 (3)
C1—H10.98C22—H22A0.97
C2—C31.537 (3)C22—H22B0.97
C2—H20.98C23—C241.503 (3)
C3—C171.523 (3)C23—H23A0.97
C3—C161.536 (3)C23—H23B0.97
C3—C41.542 (3)C24—H24A0.97
C4—C51.530 (3)C24—H24B0.97
C4—H4A0.97C25—C261.503 (4)
C4—H4B0.97C25—H25A0.97
C5—C61.558 (3)C25—H25B0.97
C5—H50.98C26—H26A0.96
C6—C191.541 (3)C26—H26B0.96
C6—C71.554 (3)C26—H26C0.96
C6—C111.557 (3)C27—C281.502 (3)
C7—C81.519 (3)C27—H27A0.97
C7—C201.520 (3)C27—H27B0.97
C7—H70.98C28—H28A0.96
C8—C91.521 (4)C28—H28B0.96
C8—H8A0.97C28—H28C0.96
C8—H8B0.97C29—C301.500 (3)
C9—C101.548 (3)C30—C311.302 (3)
C9—H9A0.97C30—H300.93
C9—H9B0.97C31—C321.467 (3)
C10—C141.544 (3)C31—H310.93
C10—C111.551 (3)O9—C331.413 (3)
C11—C121.532 (3)O9—H9O0.82
C11—H110.98C33—H33A0.96
C12—C131.502 (4)C33—H33B0.96
C13—C141.517 (3)C33—H33C0.96
C13—H13A0.97
C23—S—C22103.75 (12)H15A—C15—H15B109.5
C2—O1—H1O109.5C1—C15—H15C109.5
C21—O2—C5117.98 (16)H15A—C15—H15C109.5
C32—O8—H8O109.5H15B—C15—H15C109.5
C25—N—C27111.12 (18)C3—C16—H16A109.5
C25—N—C24114.44 (18)C3—C16—H16B109.5
C27—N—C24112.08 (17)H16A—C16—H16B109.5
C25—N—H34N103.6 (19)C3—C16—H16C109.5
C27—N—H34N113.3 (19)H16A—C16—H16C109.5
C24—N—H34N101.6 (18)H16B—C16—H16C109.5
C15—C1—C10111.62 (18)C18—C17—C3127.7 (2)
C15—C1—C2112.81 (17)C18—C17—H17116.2
C10—C1—C2111.82 (16)C3—C17—H17116.2
C15—C1—H1106.7C17—C18—H18A120.0
C10—C1—H1106.7C17—C18—H18B120.0
C2—C1—H1106.7H18A—C18—H18B120.0
O1—C2—C3109.72 (16)C6—C19—H19A109.5
O1—C2—C1109.74 (16)C6—C19—H19B109.5
C3—C2—C1114.12 (16)H19A—C19—H19B109.5
O1—C2—H2107.7C6—C19—H19C109.5
C3—C2—H2107.7H19A—C19—H19C109.5
C1—C2—H2107.7H19B—C19—H19C109.5
C17—C3—C16108.62 (16)C7—C20—H20A109.5
C17—C3—C2109.73 (16)C7—C20—H20B109.5
C16—C3—C2108.50 (16)H20A—C20—H20B109.5
C17—C3—C4112.16 (17)C7—C20—H20C109.5
C16—C3—C4104.89 (16)H20A—C20—H20C109.5
C2—C3—C4112.70 (16)H20B—C20—H20C109.5
C5—C4—C3121.10 (16)O3—C21—O2125.4 (2)
C5—C4—H4A107.1O3—C21—C22124.6 (2)
C3—C4—H4A107.1O2—C21—C22110.04 (19)
C5—C4—H4B107.1C21—C22—S112.18 (16)
C3—C4—H4B107.1C21—C22—H22A109.2
H4A—C4—H4B106.8S—C22—H22A109.2
O2—C5—C4105.28 (15)C21—C22—H22B109.2
O2—C5—C6107.65 (16)S—C22—H22B109.2
C4—C5—C6116.17 (17)H22A—C22—H22B107.9
O2—C5—H5109.2C24—C23—S112.72 (16)
C4—C5—H5109.2C24—C23—H23A109.0
C6—C5—H5109.2S—C23—H23A109.0
C19—C6—C7111.08 (17)C24—C23—H23B109.0
C19—C6—C11109.34 (17)S—C23—H23B109.0
C7—C6—C11106.06 (18)H23A—C23—H23B107.8
C19—C6—C5108.56 (18)C23—C24—N114.30 (18)
C7—C6—C5112.74 (17)C23—C24—H24A108.7
C11—C6—C5108.99 (16)N—C24—H24A108.7
C8—C7—C20111.3 (2)C23—C24—H24B108.7
C8—C7—C6111.67 (17)N—C24—H24B108.7
C20—C7—C6116.3 (2)H24A—C24—H24B107.6
C8—C7—H7105.6N—C25—C26114.1 (2)
C20—C7—H7105.6N—C25—H25A108.7
C6—C7—H7105.6C26—C25—H25A108.7
C7—C8—C9113.1 (2)N—C25—H25B108.7
C7—C8—H8A109.0C26—C25—H25B108.7
C9—C8—H8A109.0H25A—C25—H25B107.6
C7—C8—H8B109.0C25—C26—H26A109.5
C9—C8—H8B109.0C25—C26—H26B109.5
H8A—C8—H8B107.8H26A—C26—H26B109.5
C8—C9—C10114.7 (2)C25—C26—H26C109.5
C8—C9—H9A108.6H26A—C26—H26C109.5
C10—C9—H9A108.6H26B—C26—H26C109.5
C8—C9—H9B108.6N—C27—C28112.1 (2)
C10—C9—H9B108.6N—C27—H27A109.2
H9A—C9—H9B107.6C28—C27—H27A109.2
C14—C10—C9109.5 (2)N—C27—H27B109.2
C14—C10—C1110.39 (18)C28—C27—H27B109.2
C9—C10—C1111.81 (18)H27A—C27—H27B107.9
C14—C10—C11102.64 (18)C27—C28—H28A109.5
C9—C10—C11105.92 (17)C27—C28—H28B109.5
C1—C10—C11116.05 (17)H28A—C28—H28B109.5
C12—C11—C10102.18 (19)C27—C28—H28C109.5
C12—C11—C6117.78 (18)H28A—C28—H28C109.5
C10—C11—C6118.00 (17)H28B—C28—H28C109.5
C12—C11—H11105.9O6—C29—O5124.9 (2)
C10—C11—H11105.9O6—C29—C30116.0 (2)
C6—C11—H11105.9O5—C29—C30119.1 (2)
O4—C12—C13123.6 (2)C31—C30—C29125.9 (2)
O4—C12—C11128.7 (3)C31—C30—H30117.1
C13—C12—C11107.7 (2)C29—C30—H30117.1
C12—C13—C14106.5 (2)C30—C31—C32124.9 (2)
C12—C13—H13A110.4C30—C31—H31117.5
C14—C13—H13A110.4C32—C31—H31117.5
C12—C13—H13B110.4O7—C32—O8123.2 (2)
C14—C13—H13B110.4O7—C32—C31123.0 (2)
H13A—C13—H13B108.6O8—C32—C31113.7 (2)
C13—C14—C10106.1 (2)C33—O9—H9O109.5
C13—C14—H14A110.5O9—C33—H33A109.5
C10—C14—H14A110.5O9—C33—H33B109.5
C13—C14—H14B110.5H33A—C33—H33B109.5
C10—C14—H14B110.5O9—C33—H33C109.5
H14A—C14—H14B108.7H33A—C33—H33C109.5
C1—C15—H15A109.5H33B—C33—H33C109.5
C1—C15—H15B109.5
C15—C1—C2—O12.7 (2)C9—C10—C11—C1276.7 (2)
C10—C1—C2—O1129.52 (17)C1—C10—C11—C12158.58 (19)
C15—C1—C2—C3126.3 (2)C14—C10—C11—C6169.01 (18)
C10—C1—C2—C3106.88 (19)C9—C10—C11—C654.2 (2)
O1—C2—C3—C1764.1 (2)C1—C10—C11—C670.5 (2)
C1—C2—C3—C1759.5 (2)C19—C6—C11—C1254.0 (3)
O1—C2—C3—C1654.4 (2)C7—C6—C11—C1265.8 (2)
C1—C2—C3—C16178.04 (17)C5—C6—C11—C12172.57 (18)
O1—C2—C3—C4170.12 (15)C19—C6—C11—C10177.43 (18)
C1—C2—C3—C466.3 (2)C7—C6—C11—C1057.6 (2)
C17—C3—C4—C561.1 (3)C5—C6—C11—C1064.0 (2)
C16—C3—C4—C5178.85 (19)C10—C11—C12—O4149.3 (3)
C2—C3—C4—C563.3 (2)C6—C11—C12—O418.3 (4)
C21—O2—C5—C4110.79 (19)C10—C11—C12—C1330.7 (3)
C21—O2—C5—C6124.69 (18)C6—C11—C12—C13161.8 (2)
C3—C4—C5—O2134.78 (18)O4—C12—C13—C14169.2 (3)
C3—C4—C5—C6106.2 (2)C11—C12—C13—C1410.8 (3)
O2—C5—C6—C1946.4 (2)C12—C13—C14—C1013.9 (3)
C4—C5—C6—C1971.3 (2)C9—C10—C14—C1379.6 (3)
O2—C5—C6—C777.13 (19)C1—C10—C14—C13156.9 (2)
C4—C5—C6—C7165.20 (17)C11—C10—C14—C1332.6 (3)
O2—C5—C6—C11165.39 (15)C16—C3—C17—C1881.7 (3)
C4—C5—C6—C1147.7 (2)C2—C3—C17—C18159.8 (2)
C19—C6—C7—C8173.5 (2)C4—C3—C17—C1833.8 (3)
C11—C6—C7—C854.8 (2)C5—O2—C21—O35.5 (3)
C5—C6—C7—C864.4 (3)C5—O2—C21—C22174.15 (17)
C19—C6—C7—C2057.3 (3)O3—C21—C22—S82.1 (3)
C11—C6—C7—C20176.0 (2)O2—C21—C22—S97.49 (19)
C5—C6—C7—C2064.8 (3)C23—S—C22—C2171.21 (18)
C20—C7—C8—C9172.0 (2)C22—S—C23—C2471.8 (2)
C6—C7—C8—C956.3 (3)S—C23—C24—N179.51 (16)
C7—C8—C9—C1054.3 (3)C25—N—C24—C2361.6 (3)
C8—C9—C10—C14159.6 (2)C27—N—C24—C2366.1 (3)
C8—C9—C10—C177.7 (2)C27—N—C25—C26178.6 (2)
C8—C9—C10—C1149.6 (3)C24—N—C25—C2653.2 (3)
C15—C1—C10—C1455.6 (2)C25—N—C27—C2874.3 (3)
C2—C1—C10—C1471.8 (2)C24—N—C27—C28156.2 (2)
C15—C1—C10—C966.5 (2)O6—C29—C30—C31151.2 (2)
C2—C1—C10—C9166.05 (18)O5—C29—C30—C3130.2 (3)
C15—C1—C10—C11171.85 (18)C29—C30—C31—C32178.68 (19)
C2—C1—C10—C1144.4 (2)C30—C31—C32—O7178.9 (2)
C14—C10—C11—C1238.1 (2)C30—C31—C32—O80.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O9i0.821.952.772 (2)176
O8—H8O···O5ii0.821.772.586 (2)171
O9—H9O···O5iii0.821.922.738 (2)176
N—H34N···O6iii0.87 (1)1.85 (1)2.702 (2)165 (3)
C5—H5···O30.982.332.757 (3)106
C11—H11···O7iv0.982.523.399 (3)149
C19—H19B···O20.962.312.743 (3)106
C19—H19C···O40.962.352.961 (3)121
C22—H22B···O1iii0.972.503.439 (3)163
C25—H25B···O4v0.972.403.357 (3)168
C26—H26A···O6iii0.962.463.185 (3)132
C30—H30···O80.932.402.744 (3)101
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y1/2, z+1/2; (v) x, y+1, z.
 

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