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Structural characteristics of solid and liquid crystalline phases of 7OS5 (4-n-pentyl­phenyl-4′-n-heptyl­oxythio­benzoate), the achiral smectogenic mesogen with the shortest terminal carbon chain in the nOS5 homologous series, are studied by complementary methods. Simultaneously perfomed X-ray diffraction and differential scanning calorimetry occur to be a powerful tool to study metastable phases. The single crystal structure of a high-temperature phase, supercooled from the room temperature down to −183°C [orthorhombic crystal system; space group Pca21; a = 54.285 (5) Å, b = 5.5843 (3) Å, c = 14.841 (1) Å, Z = 8] is determined. Lamellar ordering of elongated molecules is stabilized by hydrogen bonds . Temperature dependence of unit-cell parameters in two crystal phases as well as structural parameters of liquid crystalline phases (smectic layer spacing, tilt angle, average distance between the long axes of molecules and correlation lengths) are determined by X-ray diffraction. The obtained results are compared with the data available for other compounds in the nOS5 homologous series.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620014481/dk5101sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014481/dk5101Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620014481/dk5101sup3.pdf
Tables S1-S2, Figs S1-S4, principal axis strain calculations

CCDC reference: 1960049

Computing details top

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28c; cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28c; data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28c; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2018); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018).

(I) top
Crystal data top
C25H34O2SDx = 1.177 Mg m3
Mr = 398.58Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pca21Cell parameters from 5154 reflections
a = 54.285 (5) Åθ = 3.2–72.5°
b = 5.5843 (3) ŵ = 1.40 mm1
c = 14.8411 (10) ÅT = 90 K
V = 4499.0 (5) Å3Needle, colourless
Z = 80.38 × 0.02 × 0.01 mm
F(000) = 1728
Data collection top
SuperNova
diffractometer (Agilent Technologies) with Atlas detector
8461 independent reflections
Radiation source: SuperNova (Cu) X-ray Source5907 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm-1Rint = 0.113
ω scansθmax = 70.1°, θmin = 3.3°
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.36.28c Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
h = 6566
Tmin = 0.562, Tmax = 1.000k = 64
34886 measured reflectionsl = 1817
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.115 w = 1/[σ2(Fo2) + (0.0856P)2 + 26.8267P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.299(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.71 e Å3
8461 reflectionsΔρmin = 0.87 e Å3
456 parametersAbsolute structure: Refined as an inversion twin.
1 restraintAbsolute structure parameter: 0.53 (7)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.70254 (5)1.0527 (5)0.5261 (2)0.0284 (6)
O10.81714 (12)0.6704 (13)0.5206 (6)0.0233 (16)
O20.70193 (14)0.6414 (14)0.4367 (5)0.0270 (18)
C10.9562 (2)0.125 (2)0.4845 (13)0.051 (4)
H1A0.9482420.2761400.5012540.076*
H1B0.9726950.1181030.5107980.076*
H1C0.9573590.1144120.4187180.076*
C20.9408 (2)0.084 (2)0.5198 (10)0.037 (3)
H2A0.9406730.0801570.5865260.044*
H2B0.9485250.2368580.5008580.044*
C30.9144 (2)0.075 (2)0.4850 (10)0.033 (3)
H3A0.9147120.0795260.4183700.040*
H3B0.9069390.0792660.5033120.040*
C40.89805 (19)0.278 (2)0.5189 (9)0.030 (3)
H4A0.8980540.2765960.5855680.036*
H4B0.9052650.4327200.4992640.036*
C50.8715 (2)0.266 (2)0.4859 (10)0.032 (3)
H5A0.8714310.2634920.4192400.039*
H5B0.8640270.1143250.5072440.039*
C60.85616 (19)0.475 (2)0.5189 (9)0.029 (3)
H6A0.8573080.4843890.5853510.035*
H6B0.8629630.6253580.4937880.035*
C70.8297 (2)0.454 (2)0.4924 (8)0.030 (3)
H7A0.8282860.4339430.4262970.036*
H7B0.8221700.3125040.5218160.036*
C80.7924 (2)0.684 (2)0.5076 (7)0.024 (2)
C90.78118 (19)0.8933 (18)0.5403 (7)0.0215 (16)
H90.7909291.0147880.5674030.026*
C100.75625 (18)0.9225 (18)0.5330 (8)0.0215 (16)
H100.7487701.0600620.5589100.026*
C110.74165 (19)0.7567 (19)0.4891 (7)0.0206 (16)
C120.7531 (2)0.5488 (18)0.4545 (7)0.0206 (16)
H120.7433900.4304080.4251240.025*
C130.7783 (2)0.5163 (19)0.4630 (7)0.022 (2)
H130.7858390.3779700.4380710.026*
C140.7145 (2)0.7824 (18)0.4766 (7)0.021 (2)
C150.6707 (2)1.0303 (18)0.5073 (8)0.0220 (17)
C160.6586 (2)1.2189 (18)0.4625 (7)0.0220 (17)
H160.6676991.3490520.4384030.026*
C170.6331 (2)1.2129 (19)0.4538 (8)0.0235 (17)
H170.6250371.3440250.4257150.028*
C180.6190 (2)1.0219 (18)0.4848 (8)0.0235 (17)
C190.6314 (2)0.831 (2)0.5259 (9)0.028 (2)
H190.6222890.6981770.5478040.033*
C200.6571 (2)0.8326 (19)0.5352 (9)0.028 (3)
H200.6652530.6981760.5607250.033*
C210.5915 (2)1.024 (2)0.4737 (9)0.029 (3)
H21A0.5878131.0363110.4085630.035*
H21B0.5851171.1716350.5026040.035*
C220.5772 (2)0.813 (2)0.5113 (8)0.030 (3)
H22A0.5843020.6635790.4865690.036*
H22B0.5793860.8091900.5775050.036*
C230.5501 (2)0.818 (2)0.4905 (10)0.036 (3)
H23A0.5478930.8221040.4242470.043*
H23B0.5429820.9680400.5151160.043*
C240.5358 (2)0.607 (2)0.5281 (11)0.045 (3)
H24A0.5380150.6036030.5943420.054*
H24B0.5429090.4577850.5034800.054*
C250.5084 (2)0.611 (3)0.5076 (12)0.052 (4)
H25A0.5015420.7671570.5241060.078*
H25B0.5001290.4850250.5423060.078*
H25C0.5058290.5826710.4430940.078*
S20.81465 (5)0.5362 (5)0.2188 (2)0.0321 (7)
O30.69885 (13)0.1982 (13)0.2227 (6)0.0268 (18)
O40.81437 (14)0.1144 (13)0.3015 (6)0.0267 (18)
C310.5588 (2)0.579 (2)0.2692 (12)0.049 (4)
H31A0.5649540.7283140.2433450.074*
H31B0.5415130.5559190.2515830.074*
H31C0.5599150.5858330.3350710.074*
C320.5741 (2)0.369 (2)0.2345 (11)0.038 (3)
H32A0.5733270.3670950.1678530.045*
H32B0.5668090.2178270.2566080.045*
C330.6008 (2)0.378 (2)0.2629 (9)0.034 (3)
H33A0.6014490.3837810.3295440.040*
H33B0.6080170.5298090.2403120.040*
C340.6168 (2)0.175 (2)0.2314 (9)0.032 (3)
H34A0.6099780.0236540.2559750.039*
H34B0.6156900.1653370.1649210.039*
C350.6435 (2)0.191 (2)0.2574 (8)0.026 (2)
H35A0.6503960.3407060.2322630.031*
H35B0.6446290.2013940.3238630.031*
C360.65937 (19)0.019 (2)0.2256 (8)0.025 (2)
H36A0.6583200.0316300.1592010.030*
H36B0.6529010.1694280.2517100.030*
C370.6859 (2)0.011 (2)0.2527 (9)0.030 (3)
H37A0.6872190.0273210.3189590.037*
H37B0.6928980.1563910.2244160.037*
C380.7237 (2)0.2029 (18)0.2367 (7)0.0217 (10)
C390.7371 (2)0.0252 (19)0.2793 (7)0.0217 (10)
H390.7289710.1106230.3038480.026*
C400.7626 (2)0.0463 (19)0.2860 (7)0.0217 (10)
H400.7718230.0778520.3137750.026*
C410.7747 (2)0.2490 (18)0.2523 (8)0.0217 (10)
C420.76084 (19)0.4248 (18)0.2098 (7)0.0217 (10)
H420.7689120.5601400.1846720.026*
C430.73565 (19)0.4065 (18)0.2034 (7)0.0217 (10)
H430.7263880.5317480.1763380.026*
C440.8018 (2)0.2642 (18)0.2628 (7)0.021 (2)
C450.8464 (2)0.4997 (18)0.2383 (7)0.022 (2)
C460.8597 (2)0.3110 (18)0.2039 (8)0.025 (3)
H460.8513410.1866160.1726730.030*
C470.88527 (19)0.2989 (18)0.2142 (8)0.023 (2)
H470.8941320.1673600.1897550.028*
C480.8979 (2)0.482 (2)0.2606 (9)0.027 (3)
C490.8842 (2)0.6700 (18)0.2939 (8)0.027 (2)
H490.8924080.7964410.3243020.032*
C500.8589 (2)0.681 (2)0.2844 (8)0.027 (3)
H500.8499930.8119410.3092800.032*
C510.9255 (2)0.474 (2)0.2752 (8)0.029 (3)
H51A0.9285630.4810970.3408830.034*
H51B0.9326450.6204330.2484030.034*
C520.9395 (2)0.261 (2)0.2382 (9)0.031 (3)
H52A0.9374080.2568680.1719070.038*
H52B0.9322670.1126070.2630330.038*
C530.9668 (2)0.266 (2)0.2598 (10)0.038 (3)
H53A0.9738930.4182070.2375110.046*
H53B0.9689250.2626180.3260570.046*
C540.9811 (2)0.062 (2)0.2197 (12)0.046 (4)
H54A0.9787840.0647890.1535330.055*
H54B0.9739460.0901210.2422070.055*
C551.0084 (3)0.062 (3)0.2397 (13)0.065 (5)
H55A1.0156670.2126780.2189030.098*
H55B1.0162490.0724620.2083270.098*
H55C1.0109850.0452780.3047330.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0266 (14)0.0289 (14)0.0297 (15)0.0006 (11)0.0009 (12)0.0067 (14)
O10.024 (4)0.023 (4)0.022 (4)0.002 (3)0.000 (3)0.004 (4)
O20.031 (4)0.024 (4)0.025 (4)0.001 (3)0.006 (3)0.007 (4)
C10.031 (7)0.036 (8)0.086 (12)0.002 (5)0.003 (7)0.003 (8)
C20.028 (6)0.035 (7)0.047 (8)0.007 (5)0.002 (6)0.000 (6)
C30.026 (6)0.030 (6)0.043 (8)0.007 (5)0.000 (5)0.011 (6)
C40.030 (6)0.027 (6)0.034 (7)0.004 (4)0.000 (5)0.011 (6)
C50.028 (6)0.031 (6)0.038 (7)0.001 (5)0.001 (5)0.004 (6)
C60.025 (6)0.031 (6)0.031 (7)0.000 (4)0.002 (5)0.004 (6)
C70.023 (6)0.035 (7)0.030 (7)0.000 (5)0.005 (5)0.002 (6)
C80.027 (6)0.027 (6)0.017 (6)0.001 (4)0.006 (4)0.001 (5)
C90.030 (4)0.016 (4)0.019 (4)0.002 (3)0.001 (3)0.005 (3)
C100.030 (4)0.016 (4)0.019 (4)0.002 (3)0.001 (3)0.005 (3)
C110.028 (4)0.018 (3)0.016 (4)0.006 (3)0.003 (3)0.007 (3)
C120.028 (4)0.018 (3)0.016 (4)0.006 (3)0.003 (3)0.007 (3)
C130.029 (6)0.018 (5)0.018 (5)0.002 (4)0.003 (4)0.004 (4)
C140.036 (6)0.020 (5)0.007 (5)0.004 (4)0.000 (4)0.003 (4)
C150.033 (4)0.009 (3)0.024 (4)0.003 (3)0.004 (3)0.004 (3)
C160.033 (4)0.009 (3)0.024 (4)0.003 (3)0.004 (3)0.004 (3)
C170.036 (5)0.012 (4)0.023 (4)0.002 (3)0.002 (3)0.010 (3)
C180.036 (5)0.012 (4)0.023 (4)0.002 (3)0.002 (3)0.010 (3)
C190.029 (6)0.032 (6)0.022 (6)0.000 (4)0.000 (5)0.001 (6)
C200.034 (6)0.020 (6)0.030 (7)0.003 (4)0.004 (5)0.001 (5)
C210.036 (7)0.020 (6)0.032 (7)0.002 (5)0.003 (5)0.009 (5)
C220.036 (6)0.024 (6)0.029 (7)0.002 (5)0.002 (5)0.009 (5)
C230.031 (7)0.028 (6)0.049 (8)0.001 (5)0.002 (6)0.002 (6)
C240.029 (7)0.049 (8)0.056 (9)0.004 (5)0.005 (7)0.003 (8)
C250.032 (7)0.052 (9)0.070 (12)0.001 (6)0.007 (7)0.003 (8)
S20.0255 (14)0.0320 (15)0.0387 (18)0.0015 (11)0.0004 (13)0.0052 (16)
O30.026 (4)0.027 (4)0.028 (5)0.000 (3)0.001 (4)0.002 (4)
O40.033 (4)0.018 (4)0.029 (5)0.002 (3)0.002 (3)0.001 (3)
C310.027 (7)0.045 (8)0.076 (11)0.002 (6)0.003 (7)0.009 (8)
C320.020 (6)0.037 (7)0.056 (9)0.001 (5)0.003 (6)0.011 (7)
C330.031 (7)0.037 (7)0.033 (7)0.003 (5)0.000 (5)0.002 (6)
C340.027 (6)0.041 (7)0.029 (7)0.001 (5)0.004 (5)0.004 (6)
C350.033 (6)0.028 (6)0.016 (5)0.001 (5)0.003 (5)0.003 (5)
C360.026 (6)0.029 (6)0.021 (6)0.001 (4)0.001 (5)0.006 (5)
C370.024 (6)0.031 (6)0.036 (7)0.001 (5)0.002 (5)0.006 (5)
C380.029 (2)0.017 (2)0.018 (2)0.0014 (17)0.0002 (19)0.009 (2)
C390.029 (2)0.017 (2)0.018 (2)0.0014 (17)0.0002 (19)0.009 (2)
C400.029 (2)0.017 (2)0.018 (2)0.0014 (17)0.0002 (19)0.009 (2)
C410.029 (2)0.017 (2)0.018 (2)0.0014 (17)0.0002 (19)0.009 (2)
C420.029 (2)0.017 (2)0.018 (2)0.0014 (17)0.0002 (19)0.009 (2)
C430.029 (2)0.017 (2)0.018 (2)0.0014 (17)0.0002 (19)0.009 (2)
C440.030 (6)0.020 (5)0.012 (5)0.002 (4)0.002 (4)0.002 (4)
C450.034 (6)0.011 (5)0.022 (6)0.004 (4)0.004 (5)0.009 (4)
C460.042 (7)0.013 (5)0.019 (6)0.007 (4)0.001 (5)0.000 (5)
C470.030 (6)0.016 (5)0.023 (6)0.003 (4)0.004 (5)0.000 (5)
C480.022 (6)0.030 (6)0.030 (6)0.004 (5)0.000 (5)0.003 (5)
C490.041 (7)0.009 (5)0.031 (6)0.002 (4)0.002 (5)0.000 (5)
C500.038 (7)0.019 (6)0.023 (6)0.003 (5)0.004 (5)0.003 (5)
C510.034 (7)0.024 (6)0.027 (6)0.001 (5)0.003 (5)0.004 (5)
C520.028 (6)0.032 (6)0.034 (7)0.002 (5)0.002 (5)0.000 (5)
C530.032 (7)0.032 (7)0.051 (8)0.001 (5)0.002 (6)0.000 (6)
C540.033 (7)0.042 (8)0.063 (10)0.003 (5)0.002 (7)0.019 (8)
C550.038 (8)0.066 (11)0.092 (14)0.011 (7)0.010 (8)0.023 (10)
Geometric parameters (Å, º) top
S1—C151.753 (12)S2—C451.759 (11)
S1—C141.800 (11)S2—C441.795 (11)
O1—C81.358 (13)O3—C381.364 (12)
O1—C71.450 (13)O3—C371.436 (14)
O2—C141.199 (13)O4—C441.224 (13)
C1—C21.527 (17)C31—C321.527 (18)
C1—H1A0.9800C31—H31A0.9800
C1—H1B0.9800C31—H31B0.9800
C1—H1C0.9800C31—H31C0.9800
C2—C31.526 (15)C32—C331.509 (16)
C2—H2A0.9900C32—H32A0.9900
C2—H2B0.9900C32—H32B0.9900
C3—C41.526 (15)C33—C341.504 (16)
C3—H3A0.9900C33—H33A0.9900
C3—H3B0.9900C33—H33B0.9900
C4—C51.521 (15)C34—C351.504 (15)
C4—H4A0.9900C34—H34A0.9900
C4—H4B0.9900C34—H34B0.9900
C5—C61.518 (16)C35—C361.528 (15)
C5—H5A0.9900C35—H35A0.9900
C5—H5B0.9900C35—H35B0.9900
C6—C71.494 (15)C36—C371.503 (14)
C6—H6A0.9900C36—H36A0.9900
C6—H6B0.9900C36—H36B0.9900
C7—H7A0.9900C37—H37A0.9900
C7—H7B0.9900C37—H37B0.9900
C8—C131.379 (15)C38—C391.384 (15)
C8—C91.406 (15)C38—C431.400 (15)
C9—C101.368 (14)C39—C401.391 (14)
C9—H90.9500C39—H390.9500
C10—C111.382 (13)C40—C411.402 (15)
C10—H100.9500C40—H400.9500
C11—C121.412 (14)C41—C421.390 (15)
C11—C141.492 (15)C41—C441.478 (15)
C12—C131.386 (15)C42—C431.375 (14)
C12—H120.9500C42—H420.9500
C13—H130.9500C43—H430.9500
C15—C201.392 (15)C45—C461.375 (14)
C15—C161.411 (15)C45—C501.399 (15)
C16—C171.387 (16)C46—C471.399 (15)
C16—H160.9500C46—H460.9500
C17—C181.391 (15)C47—C481.411 (15)
C17—H170.9500C47—H470.9500
C18—C191.401 (15)C48—C491.381 (15)
C18—C211.504 (16)C48—C511.512 (15)
C19—C201.400 (15)C49—C501.381 (16)
C19—H190.9500C49—H490.9500
C20—H200.9500C50—H500.9500
C21—C221.518 (16)C51—C521.512 (15)
C21—H21A0.9900C51—H51A0.9900
C21—H21B0.9900C51—H51B0.9900
C22—C231.506 (16)C52—C531.519 (16)
C22—H22A0.9900C52—H52A0.9900
C22—H22B0.9900C52—H52B0.9900
C23—C241.518 (17)C53—C541.499 (17)
C23—H23A0.9900C53—H53A0.9900
C23—H23B0.9900C53—H53B0.9900
C24—C251.518 (16)C54—C551.513 (17)
C24—H24A0.9900C54—H54A0.9900
C24—H24B0.9900C54—H54B0.9900
C25—H25A0.9800C55—H55A0.9800
C25—H25B0.9800C55—H55B0.9800
C25—H25C0.9800C55—H55C0.9800
C15—S1—C14103.4 (5)C45—S2—C44103.0 (5)
C8—O1—C7118.0 (8)C38—O3—C37116.9 (8)
C2—C1—H1A109.5C32—C31—H31A109.5
C2—C1—H1B109.5C32—C31—H31B109.5
H1A—C1—H1B109.5H31A—C31—H31B109.5
C2—C1—H1C109.5C32—C31—H31C109.5
H1A—C1—H1C109.5H31A—C31—H31C109.5
H1B—C1—H1C109.5H31B—C31—H31C109.5
C3—C2—C1111.8 (12)C33—C32—C31113.8 (12)
C3—C2—H2A109.3C33—C32—H32A108.8
C1—C2—H2A109.3C31—C32—H32A108.8
C3—C2—H2B109.3C33—C32—H32B108.8
C1—C2—H2B109.3C31—C32—H32B108.8
H2A—C2—H2B107.9H32A—C32—H32B107.7
C4—C3—C2114.2 (10)C34—C33—C32116.1 (11)
C4—C3—H3A108.7C34—C33—H33A108.3
C2—C3—H3A108.7C32—C33—H33A108.3
C4—C3—H3B108.7C34—C33—H33B108.3
C2—C3—H3B108.7C32—C33—H33B108.3
H3A—C3—H3B107.6H33A—C33—H33B107.4
C5—C4—C3114.1 (10)C33—C34—C35115.5 (10)
C5—C4—H4A108.7C33—C34—H34A108.4
C3—C4—H4A108.7C35—C34—H34A108.4
C5—C4—H4B108.7C33—C34—H34B108.4
C3—C4—H4B108.7C35—C34—H34B108.4
H4A—C4—H4B107.6H34A—C34—H34B107.5
C6—C5—C4112.4 (10)C34—C35—C36114.8 (10)
C6—C5—H5A109.1C34—C35—H35A108.6
C4—C5—H5A109.1C36—C35—H35A108.6
C6—C5—H5B109.1C34—C35—H35B108.6
C4—C5—H5B109.1C36—C35—H35B108.6
H5A—C5—H5B107.9H35A—C35—H35B107.6
C7—C6—C5112.5 (10)C37—C36—C35111.8 (10)
C7—C6—H6A109.1C37—C36—H36A109.3
C5—C6—H6A109.1C35—C36—H36A109.3
C7—C6—H6B109.1C37—C36—H36B109.3
C5—C6—H6B109.1C35—C36—H36B109.3
H6A—C6—H6B107.8H36A—C36—H36B107.9
O1—C7—C6108.0 (10)O3—C37—C36107.2 (9)
O1—C7—H7A110.1O3—C37—H37A110.3
C6—C7—H7A110.1C36—C37—H37A110.3
O1—C7—H7B110.1O3—C37—H37B110.3
C6—C7—H7B110.1C36—C37—H37B110.3
H7A—C7—H7B108.4H37A—C37—H37B108.5
O1—C8—C13125.5 (10)O3—C38—C39125.2 (10)
O1—C8—C9115.2 (9)O3—C38—C43114.8 (9)
C13—C8—C9119.2 (10)C39—C38—C43120.0 (10)
C10—C9—C8120.1 (9)C38—C39—C40119.7 (10)
C10—C9—H9119.9C38—C39—H39120.2
C8—C9—H9119.9C40—C39—H39120.2
C9—C10—C11121.6 (9)C39—C40—C41120.7 (10)
C9—C10—H10119.2C39—C40—H40119.6
C11—C10—H10119.2C41—C40—H40119.6
C10—C11—C12118.1 (10)C42—C41—C40118.5 (11)
C10—C11—C14124.1 (9)C42—C41—C44123.1 (10)
C12—C11—C14117.8 (9)C40—C41—C44118.5 (9)
C13—C12—C11120.5 (9)C43—C42—C41121.3 (10)
C13—C12—H12119.8C43—C42—H42119.4
C11—C12—H12119.8C41—C42—H42119.4
C8—C13—C12120.3 (10)C42—C43—C38119.8 (10)
C8—C13—H13119.8C42—C43—H43120.1
C12—C13—H13119.8C38—C43—H43120.1
O2—C14—C11124.1 (9)O4—C44—C41124.4 (10)
O2—C14—S1123.1 (9)O4—C44—S2122.0 (9)
C11—C14—S1112.7 (7)C41—C44—S2113.4 (7)
C20—C15—C16118.9 (10)C46—C45—C50118.8 (10)
C20—C15—S1122.2 (9)C46—C45—S2122.8 (8)
C16—C15—S1118.9 (8)C50—C45—S2118.1 (8)
C17—C16—C15119.5 (10)C45—C46—C47121.2 (10)
C17—C16—H16120.2C45—C46—H46119.4
C15—C16—H16120.2C47—C46—H46119.4
C16—C17—C18122.4 (10)C46—C47—C48120.1 (10)
C16—C17—H17118.8C46—C47—H47119.9
C18—C17—H17118.8C48—C47—H47119.9
C17—C18—C19117.6 (11)C49—C48—C47117.5 (10)
C17—C18—C21120.2 (10)C49—C48—C51120.4 (10)
C19—C18—C21122.2 (10)C47—C48—C51122.1 (10)
C20—C19—C18121.1 (10)C48—C49—C50122.4 (10)
C20—C19—H19119.4C48—C49—H49118.8
C18—C19—H19119.4C50—C49—H49118.8
C15—C20—C19120.3 (11)C49—C50—C45119.9 (10)
C15—C20—H20119.8C49—C50—H50120.0
C19—C20—H20119.8C45—C50—H50120.0
C18—C21—C22117.4 (10)C48—C51—C52117.9 (10)
C18—C21—H21A107.9C48—C51—H51A107.8
C22—C21—H21A107.9C52—C51—H51A107.8
C18—C21—H21B107.9C48—C51—H51B107.8
C22—C21—H21B107.9C52—C51—H51B107.8
H21A—C21—H21B107.2H51A—C51—H51B107.2
C23—C22—C21114.2 (10)C51—C52—C53113.7 (10)
C23—C22—H22A108.7C51—C52—H52A108.8
C21—C22—H22A108.7C53—C52—H52A108.8
C23—C22—H22B108.7C51—C52—H52B108.8
C21—C22—H22B108.7C53—C52—H52B108.8
H22A—C22—H22B107.6H52A—C52—H52B107.7
C22—C23—C24114.1 (11)C54—C53—C52114.0 (11)
C22—C23—H23A108.7C54—C53—H53A108.8
C24—C23—H23A108.7C52—C53—H53A108.8
C22—C23—H23B108.7C54—C53—H53B108.8
C24—C23—H23B108.7C52—C53—H53B108.8
H23A—C23—H23B107.6H53A—C53—H53B107.7
C23—C24—C25114.6 (12)C53—C54—C55115.3 (12)
C23—C24—H24A108.6C53—C54—H54A108.5
C25—C24—H24A108.6C55—C54—H54A108.5
C23—C24—H24B108.6C53—C54—H54B108.5
C25—C24—H24B108.6C55—C54—H54B108.5
H24A—C24—H24B107.6H54A—C54—H54B107.5
C24—C25—H25A109.5C54—C55—H55A109.5
C24—C25—H25B109.5C54—C55—H55B109.5
H25A—C25—H25B109.5H55A—C55—H55B109.5
C24—C25—H25C109.5C54—C55—H55C109.5
H25A—C25—H25C109.5H55A—C55—H55C109.5
H25B—C25—H25C109.5H55B—C55—H55C109.5
C1—C2—C3—C4179.4 (12)C31—C32—C33—C34179.3 (12)
C2—C3—C4—C5178.6 (11)C32—C33—C34—C35177.9 (11)
C3—C4—C5—C6178.3 (11)C33—C34—C35—C36179.4 (10)
C4—C5—C6—C7175.8 (11)C34—C35—C36—C37179.1 (10)
C8—O1—C7—C6176.4 (9)C38—O3—C37—C36177.0 (9)
C5—C6—C7—O1175.5 (10)C35—C36—C37—O3177.9 (9)
C7—O1—C8—C135.4 (16)C37—O3—C38—C391.6 (16)
C7—O1—C8—C9177.1 (10)C37—O3—C38—C43177.7 (9)
O1—C8—C9—C10178.1 (9)O3—C38—C39—C40177.2 (9)
C13—C8—C9—C104.3 (16)C43—C38—C39—C402.1 (15)
C8—C9—C10—C114.1 (17)C38—C39—C40—C411.8 (14)
C9—C10—C11—C122.6 (17)C39—C40—C41—C421.8 (15)
C9—C10—C11—C14178.0 (10)C39—C40—C41—C44178.9 (9)
C10—C11—C12—C131.4 (16)C40—C41—C42—C432.3 (15)
C14—C11—C12—C13179.2 (10)C44—C41—C42—C43178.4 (9)
O1—C8—C13—C12179.5 (10)C41—C42—C43—C382.7 (15)
C9—C8—C13—C123.1 (17)O3—C38—C43—C42176.8 (9)
C11—C12—C13—C81.7 (16)C39—C38—C43—C422.6 (15)
C10—C11—C14—O2178.2 (11)C42—C41—C44—O4178.5 (11)
C12—C11—C14—O22.4 (16)C40—C41—C44—O42.3 (15)
C10—C11—C14—S10.6 (14)C42—C41—C44—S22.1 (13)
C12—C11—C14—S1178.8 (8)C40—C41—C44—S2178.6 (8)
C15—S1—C14—O24.2 (11)C45—S2—C44—O44.8 (11)
C15—S1—C14—C11177.0 (8)C45—S2—C44—C41178.8 (7)
C14—S1—C15—C2054.8 (11)C44—S2—C45—C4658.3 (11)
C14—S1—C15—C16125.2 (9)C44—S2—C45—C50127.1 (9)
C20—C15—C16—C175.3 (16)C50—C45—C46—C470.2 (17)
S1—C15—C16—C17174.7 (8)S2—C45—C46—C47174.3 (8)
C15—C16—C17—C182.6 (16)C45—C46—C47—C480.2 (17)
C16—C17—C18—C190.0 (16)C46—C47—C48—C490.7 (17)
C16—C17—C18—C21180.0 (10)C46—C47—C48—C51178.6 (11)
C17—C18—C19—C200.1 (17)C47—C48—C49—C501.2 (18)
C21—C18—C19—C20179.9 (11)C51—C48—C49—C50178.1 (11)
C16—C15—C20—C195.5 (17)C48—C49—C50—C451.3 (17)
S1—C15—C20—C19174.5 (9)C46—C45—C50—C490.8 (17)
C18—C19—C20—C153.0 (18)S2—C45—C50—C49174.1 (9)
C17—C18—C21—C22178.4 (10)C49—C48—C51—C52179.3 (11)
C19—C18—C21—C221.6 (16)C47—C48—C51—C520.0 (17)
C18—C21—C22—C23174.9 (10)C48—C51—C52—C53177.6 (11)
C21—C22—C23—C24179.9 (11)C51—C52—C53—C54177.3 (12)
C22—C23—C24—C25180.0 (12)C52—C53—C54—C55179.7 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O3i0.952.583.377 (13)141
C16—H16···O2ii0.952.473.355 (13)154
C20—H20···S2iii0.952.743.538 (13)142
C50—H50···O4ii0.952.573.429 (14)151
C7—H7A···O40.992.683.508 (15)141
C37—H37A···O2iv0.992.673.461 (16)137
Symmetry codes: (i) x+3/2, y+1, z+1/2; (ii) x, y+1, z; (iii) x+3/2, y, z+1/2; (iv) x, y1, z.
 

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