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organic compounds
(4aSR,9aSR)-9a-Methyl-5,5-dioxo-1,2,4a,6,7,9a-hexahydro-8-oxa-5λ6-thiabenzo-1,4-cyclohepten-9-one
The title compound, C10H14O4S, crystallizes as a racemic mixture in space group P21/c, with two crystallographically independent molecules in the asymmetric unit. The seven-membered rings exhibit a chair conformation.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007639/bt6436sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007639/bt6436Isup2.hkl |
CCDC reference: 239128
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.002 Å - R factor = 0.038
- wR factor = 0.102
- Data-to-parameter ratio = 14.5
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.002 ÅcheckCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.585 0.916 Tmin' and Tmax expected: 0.882 0.916 RR' = 0.663 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.66 PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C9 .. 7.26 su
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O8 - C9 .. 5.34 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Alert level B
Alert level C
Computing details top
Data collection: SMART (Bruker, 1997–2000); cell refinement: SAINT-Plus (Bruker, 1997–1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
(I) top
Crystal data top
| C10H14O4S | F(000) = 976 |
| Mr = 230.27 | Dx = 1.477 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.9599 (8) Å | Cell parameters from 8706 reflections |
| b = 22.4386 (16) Å | θ = 2.6–28.3° |
| c = 9.1966 (7) Å | µ = 0.30 mm−1 |
| β = 113.690 (1)° | T = 100 K |
| V = 2071.1 (3) Å3 | Block, colourless |
| Z = 8 | 0.4 × 0.4 × 0.29 mm |
Data collection top
| Bruker SMART APEX CCD diffractometer | 5162 independent reflections |
| Radiation source: fine-focus sealed tube | 4902 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.032 |
| ω scans | θmax = 28.3°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1997–1999) | h = −14→14 |
| Tmin = 0.585, Tmax = 0.916 | k = −29→29 |
| 21071 measured reflections | l = −12→12 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.102 | Only H-atom coordinates refined |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0539P)2 + 1.337P] where P = (Fo2 + 2Fc2)/3 |
| 5162 reflections | (Δ/σ)max = 0.001 |
| 355 parameters | Δρmax = 0.78 e Å−3 |
| 0 restraints | Δρmin = −0.45 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 | ||
| C1 | 0.93555 (14) | 0.14741 (7) | 0.49486 (17) | 0.0191 (3) | |
| H1B | 0.8987 (19) | 0.1837 (9) | 0.522 (2) | 0.023* | |
| H1A | 0.8610 (19) | 0.1185 (9) | 0.446 (2) | 0.023* | |
| O1 | 0.79491 (10) | 0.06710 (5) | 0.17016 (12) | 0.0202 (2) | |
| C2 | 1.04209 (16) | 0.11855 (8) | 0.64078 (18) | 0.0244 (3) | |
| H2A | 1.102 (2) | 0.1498 (10) | 0.704 (2) | 0.029* | |
| H2B | 1.001 (2) | 0.1017 (9) | 0.703 (2) | 0.029* | |
| O2 | 0.97912 (12) | 0.00677 (5) | 0.15568 (13) | 0.0244 (2) | |
| C3 | 1.11669 (15) | 0.07123 (7) | 0.59524 (18) | 0.0228 (3) | |
| H3 | 1.168 (2) | 0.0439 (9) | 0.677 (2) | 0.027* | |
| O3 | 0.76793 (10) | 0.20463 (5) | 0.21895 (13) | 0.0232 (2) | |
| C4 | 1.11592 (14) | 0.06593 (7) | 0.45123 (18) | 0.0200 (3) | |
| H4A | 1.1629 (19) | 0.0347 (9) | 0.429 (2) | 0.024* | |
| C4A | 1.04464 (13) | 0.10805 (6) | 0.31617 (15) | 0.0146 (2) | |
| H4B | 1.1041 (18) | 0.1202 (8) | 0.269 (2) | 0.018* | |
| S5 | 0.92202 (3) | 0.064467 (14) | 0.15659 (4) | 0.01532 (9) | |
| C6 | 0.90426 (14) | 0.10181 (6) | −0.02254 (16) | 0.0173 (3) | |
| H6A | 0.9925 (19) | 0.1058 (9) | −0.019 (2) | 0.021* | |
| H6B | 0.8525 (18) | 0.0749 (9) | −0.104 (2) | 0.021* | |
| C7 | 0.83455 (15) | 0.16137 (6) | −0.03976 (17) | 0.0195 (3) | |
| H7A | 0.8323 (19) | 0.1840 (9) | −0.133 (2) | 0.023* | |
| H7B | 0.7381 (19) | 0.1569 (9) | −0.051 (2) | 0.023* | |
| O8 | 0.91088 (10) | 0.19662 (4) | 0.09941 (12) | 0.0187 (2) | |
| C9 | 0.87542 (14) | 0.19003 (6) | 0.22489 (16) | 0.0171 (3) | |
| C9A | 0.98783 (13) | 0.16361 (6) | 0.36847 (16) | 0.0151 (2) | |
| C10 | 1.10009 (15) | 0.21055 (7) | 0.43004 (19) | 0.0234 (3) | |
| H10A | 1.121 (2) | 0.2253 (10) | 0.341 (3) | 0.035* | |
| H10B | 1.177 (2) | 0.1920 (10) | 0.508 (3) | 0.035* | |
| H10C | 1.074 (2) | 0.2448 (10) | 0.478 (3) | 0.035* | |
| C1' | 0.32610 (13) | 0.05026 (6) | 0.19669 (17) | 0.0160 (2) | |
| H1A' | 0.3131 (18) | 0.0620 (8) | 0.293 (2) | 0.019* | |
| H1B' | 0.2457 (18) | 0.0469 (8) | 0.112 (2) | 0.019* | |
| O1' | 0.42213 (11) | 0.14709 (4) | 0.47853 (13) | 0.0197 (2) | |
| C2' | 0.39663 (13) | −0.00994 (6) | 0.22937 (17) | 0.0172 (3) | |
| H2B' | 0.3574 (18) | −0.0363 (9) | 0.280 (2) | 0.021* | |
| H2A' | 0.3879 (18) | −0.0302 (9) | 0.130 (2) | 0.021* | |
| O2' | 0.66913 (11) | 0.14200 (5) | 0.59954 (12) | 0.0234 (2) | |
| C3' | 0.54107 (14) | −0.00461 (6) | 0.33648 (17) | 0.0176 (3) | |
| H3' | 0.5851 (18) | −0.0403 (9) | 0.383 (2) | 0.021* | |
| O3' | 0.21756 (10) | 0.16328 (5) | 0.10992 (14) | 0.0232 (2) | |
| C4' | 0.60739 (13) | 0.04676 (6) | 0.37097 (17) | 0.0166 (3) | |
| H4A' | 0.6988 (18) | 0.0489 (8) | 0.442 (2) | 0.020* | |
| C4A' | 0.54725 (12) | 0.10599 (6) | 0.30114 (15) | 0.0129 (2) | |
| H4B' | 0.6094 (17) | 0.1270 (8) | 0.264 (2) | 0.016* | |
| S5' | 0.54750 (3) | 0.153594 (14) | 0.46231 (4) | 0.01483 (9) | |
| C6' | 0.55733 (14) | 0.22842 (6) | 0.40071 (17) | 0.0177 (3) | |
| H6B' | 0.5708 (18) | 0.2511 (9) | 0.489 (2) | 0.021* | |
| H6A' | 0.6314 (19) | 0.2304 (9) | 0.379 (2) | 0.021* | |
| C7' | 0.43262 (15) | 0.24740 (6) | 0.26064 (17) | 0.0186 (3) | |
| H7B' | 0.3562 (19) | 0.2476 (9) | 0.285 (2) | 0.022* | |
| H7A' | 0.4461 (19) | 0.2857 (9) | 0.223 (2) | 0.022* | |
| O8' | 0.41163 (10) | 0.20533 (4) | 0.13295 (12) | 0.0168 (2) | |
| C9' | 0.33245 (13) | 0.15749 (6) | 0.13246 (16) | 0.0156 (3) | |
| C9A' | 0.40846 (12) | 0.09908 (6) | 0.16131 (15) | 0.0134 (2) | |
| C10' | 0.43230 (16) | 0.08504 (7) | 0.01056 (17) | 0.0213 (3) | |
| H10D | 0.352 (2) | 0.0751 (10) | −0.074 (3) | 0.032* | |
| H10F | 0.490 (2) | 0.0508 (10) | 0.032 (3) | 0.032* | |
| H10E | 0.473 (2) | 0.1192 (10) | −0.019 (3) | 0.032* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0194 (6) | 0.0218 (7) | 0.0185 (6) | 0.0013 (5) | 0.0102 (5) | −0.0005 (5) |
| O1 | 0.0176 (5) | 0.0222 (5) | 0.0219 (5) | −0.0047 (4) | 0.0092 (4) | −0.0030 (4) |
| C2 | 0.0275 (7) | 0.0291 (8) | 0.0166 (6) | 0.0017 (6) | 0.0087 (6) | 0.0024 (6) |
| O2 | 0.0365 (6) | 0.0129 (5) | 0.0274 (5) | 0.0040 (4) | 0.0166 (5) | −0.0008 (4) |
| C3 | 0.0191 (7) | 0.0246 (7) | 0.0217 (7) | 0.0020 (5) | 0.0050 (5) | 0.0061 (6) |
| O3 | 0.0194 (5) | 0.0239 (5) | 0.0256 (5) | 0.0071 (4) | 0.0085 (4) | 0.0015 (4) |
| C4 | 0.0151 (6) | 0.0207 (7) | 0.0224 (7) | 0.0047 (5) | 0.0058 (5) | 0.0047 (5) |
| C4A | 0.0127 (5) | 0.0149 (6) | 0.0169 (6) | 0.0004 (4) | 0.0066 (5) | 0.0006 (5) |
| S5 | 0.01771 (17) | 0.01183 (16) | 0.01759 (16) | −0.00054 (11) | 0.00830 (13) | −0.00088 (11) |
| C6 | 0.0208 (6) | 0.0175 (6) | 0.0144 (6) | −0.0012 (5) | 0.0078 (5) | −0.0001 (5) |
| C7 | 0.0217 (7) | 0.0185 (6) | 0.0160 (6) | 0.0012 (5) | 0.0053 (5) | 0.0011 (5) |
| O8 | 0.0210 (5) | 0.0153 (5) | 0.0194 (5) | −0.0014 (4) | 0.0076 (4) | 0.0002 (4) |
| C9 | 0.0203 (6) | 0.0090 (5) | 0.0183 (6) | 0.0003 (5) | 0.0039 (5) | −0.0013 (5) |
| C9A | 0.0138 (6) | 0.0141 (6) | 0.0172 (6) | −0.0004 (4) | 0.0060 (5) | −0.0010 (5) |
| C10 | 0.0199 (7) | 0.0215 (7) | 0.0265 (7) | −0.0070 (5) | 0.0069 (6) | −0.0049 (6) |
| C1' | 0.0124 (6) | 0.0141 (6) | 0.0206 (6) | −0.0016 (5) | 0.0056 (5) | −0.0010 (5) |
| O1' | 0.0246 (5) | 0.0168 (5) | 0.0238 (5) | −0.0021 (4) | 0.0162 (4) | −0.0018 (4) |
| C2' | 0.0174 (6) | 0.0129 (6) | 0.0212 (6) | −0.0023 (5) | 0.0075 (5) | −0.0017 (5) |
| O2' | 0.0249 (5) | 0.0213 (5) | 0.0166 (5) | −0.0031 (4) | 0.0007 (4) | 0.0001 (4) |
| C3' | 0.0180 (6) | 0.0142 (6) | 0.0218 (6) | 0.0029 (5) | 0.0091 (5) | 0.0019 (5) |
| O3' | 0.0145 (5) | 0.0196 (5) | 0.0337 (6) | 0.0035 (4) | 0.0077 (4) | 0.0062 (4) |
| C4' | 0.0125 (6) | 0.0161 (6) | 0.0203 (6) | 0.0022 (5) | 0.0057 (5) | 0.0018 (5) |
| C4A' | 0.0116 (5) | 0.0122 (5) | 0.0156 (6) | −0.0002 (4) | 0.0061 (5) | −0.0007 (4) |
| S5' | 0.01728 (17) | 0.01239 (16) | 0.01461 (16) | −0.00211 (11) | 0.00619 (13) | −0.00067 (11) |
| C6' | 0.0218 (6) | 0.0123 (6) | 0.0203 (6) | −0.0039 (5) | 0.0098 (5) | −0.0020 (5) |
| C7' | 0.0225 (7) | 0.0123 (6) | 0.0230 (7) | 0.0010 (5) | 0.0114 (5) | 0.0003 (5) |
| O8' | 0.0188 (5) | 0.0136 (4) | 0.0194 (5) | −0.0012 (3) | 0.0090 (4) | 0.0014 (4) |
| C9' | 0.0151 (6) | 0.0148 (6) | 0.0162 (6) | 0.0003 (5) | 0.0054 (5) | 0.0016 (5) |
| C9A' | 0.0121 (5) | 0.0130 (6) | 0.0144 (6) | 0.0005 (4) | 0.0047 (5) | 0.0000 (4) |
| C10' | 0.0276 (7) | 0.0211 (7) | 0.0172 (6) | 0.0002 (6) | 0.0112 (6) | −0.0022 (5) |
Geometric parameters (Å, º) top
| C1—C2 | 1.525 (2) | C1'—C2' | 1.5251 (18) |
| C1—C9A | 1.5319 (19) | C1'—C9A' | 1.5353 (18) |
| C1—H1B | 0.98 (2) | C1'—H1A' | 0.984 (19) |
| C1—H1A | 1.00 (2) | C1'—H1B' | 0.916 (19) |
| O1—S5 | 1.4489 (10) | O1'—S5' | 1.4478 (10) |
| C2—C3 | 1.499 (2) | C2'—C3' | 1.4959 (19) |
| C2—H2A | 0.98 (2) | C2'—H2B' | 0.956 (19) |
| C2—H2B | 0.94 (2) | C2'—H2A' | 0.987 (19) |
| O2—S5 | 1.4395 (11) | O2'—S5' | 1.4441 (11) |
| C3—C4 | 1.326 (2) | C3'—C4' | 1.3313 (19) |
| C3—H3 | 0.96 (2) | C3'—H3' | 0.944 (19) |
| O3—C9 | 1.2028 (17) | O3'—C9' | 1.1982 (17) |
| C4—C4A | 1.5056 (18) | C4'—C4A' | 1.5078 (18) |
| C4—H4A | 0.94 (2) | C4'—H4A' | 0.952 (18) |
| C4A—C9A | 1.5536 (18) | C4A'—C9A' | 1.5555 (17) |
| C4A—S5 | 1.8253 (13) | C4A'—S5' | 1.8261 (13) |
| C4A—H4B | 0.955 (18) | C4A'—H4B' | 0.997 (18) |
| S5—C6 | 1.7878 (14) | S5'—C6' | 1.7890 (14) |
| C6—C7 | 1.5159 (19) | C6'—C7' | 1.515 (2) |
| C6—H6A | 0.959 (19) | C6'—H6B' | 0.92 (2) |
| C6—H6B | 0.951 (19) | C6'—H6A' | 0.910 (19) |
| C7—O8 | 1.4502 (17) | C7'—O8' | 1.4513 (17) |
| C7—H7A | 0.98 (2) | C7'—H7B' | 0.951 (19) |
| C7—H7B | 1.02 (2) | C7'—H7A' | 0.96 (2) |
| O8—C9 | 1.3656 (17) | O8'—C9' | 1.3793 (16) |
| C9—C9A | 1.5184 (18) | C9'—C9A' | 1.5180 (18) |
| C9A—C10 | 1.5441 (19) | C9A'—C10' | 1.5428 (18) |
| C10—H10A | 0.99 (2) | C10'—H10D | 0.94 (2) |
| C10—H10B | 0.96 (2) | C10'—H10F | 0.97 (2) |
| C10—H10C | 0.99 (2) | C10'—H10E | 0.97 (2) |
| C2—C1—C9A | 112.39 (12) | C2'—C1'—C9A' | 112.28 (11) |
| C2—C1—H1B | 112.3 (11) | C2'—C1'—H1A' | 107.7 (11) |
| C9A—C1—H1B | 108.0 (11) | C9A'—C1'—H1A' | 107.9 (11) |
| C2—C1—H1A | 108.5 (11) | C2'—C1'—H1B' | 109.5 (12) |
| C9A—C1—H1A | 107.7 (11) | C9A'—C1'—H1B' | 109.0 (12) |
| H1B—C1—H1A | 107.8 (16) | H1A'—C1'—H1B' | 110.5 (16) |
| C3—C2—C1 | 111.46 (12) | C3'—C2'—C1' | 112.18 (11) |
| C3—C2—H2A | 111.6 (12) | C3'—C2'—H2B' | 107.0 (11) |
| C1—C2—H2A | 108.3 (12) | C1'—C2'—H2B' | 110.6 (11) |
| C3—C2—H2B | 109.6 (13) | C3'—C2'—H2A' | 109.2 (11) |
| C1—C2—H2B | 108.9 (13) | C1'—C2'—H2A' | 111.9 (11) |
| H2A—C2—H2B | 106.9 (17) | H2B'—C2'—H2A' | 105.7 (15) |
| C4—C3—C2 | 123.87 (14) | C4'—C3'—C2' | 123.93 (12) |
| C4—C3—H3 | 119.7 (12) | C4'—C3'—H3' | 119.8 (11) |
| C2—C3—H3 | 116.5 (12) | C2'—C3'—H3' | 116.3 (11) |
| C3—C4—C4A | 124.09 (13) | C3'—C4'—C4A' | 123.94 (12) |
| C3—C4—H4A | 119.8 (12) | C3'—C4'—H4A' | 122.1 (11) |
| C4A—C4—H4A | 116.1 (12) | C4A'—C4'—H4A' | 114.0 (11) |
| C4—C4A—C9A | 112.83 (11) | C4'—C4A'—C9A' | 112.28 (11) |
| C4—C4A—S5 | 107.29 (9) | C4'—C4A'—S5' | 108.18 (9) |
| C9A—C4A—S5 | 114.94 (9) | C9A'—C4A'—S5' | 114.29 (8) |
| C4—C4A—H4B | 109.3 (11) | C4'—C4A'—H4B' | 108.7 (10) |
| C9A—C4A—H4B | 110.0 (11) | C9A'—C4A'—H4B' | 109.8 (10) |
| S5—C4A—H4B | 101.9 (11) | S5'—C4A'—H4B' | 103.1 (10) |
| O2—S5—O1 | 118.19 (7) | O2'—S5'—O1' | 118.21 (7) |
| O2—S5—C6 | 107.63 (7) | O2'—S5'—C6' | 107.09 (7) |
| O1—S5—C6 | 107.93 (6) | O1'—S5'—C6' | 107.91 (6) |
| O2—S5—C4A | 107.77 (7) | O2'—S5'—C4A' | 107.69 (6) |
| O1—S5—C4A | 109.37 (6) | O1'—S5'—C4A' | 109.43 (6) |
| C6—S5—C4A | 105.20 (6) | C6'—S5'—C4A' | 105.82 (6) |
| C7—C6—S5 | 111.91 (10) | C7'—C6'—S5' | 112.63 (10) |
| C7—C6—H6A | 112.3 (12) | C7'—C6'—H6B' | 111.4 (12) |
| S5—C6—H6A | 106.2 (11) | S5'—C6'—H6B' | 104.5 (12) |
| C7—C6—H6B | 111.2 (11) | C7'—C6'—H6A' | 112.4 (12) |
| S5—C6—H6B | 103.7 (12) | S5'—C6'—H6A' | 106.7 (12) |
| H6A—C6—H6B | 111.1 (16) | H6B'—C6'—H6A' | 108.8 (16) |
| O8—C7—C6 | 107.51 (11) | O8'—C7'—C6' | 107.50 (11) |
| O8—C7—H7A | 106.7 (11) | O8'—C7'—H7B' | 109.0 (12) |
| C6—C7—H7A | 112.4 (11) | C6'—C7'—H7B' | 112.3 (11) |
| O8—C7—H7B | 110.5 (11) | O8'—C7'—H7A' | 106.9 (12) |
| C6—C7—H7B | 112.4 (11) | C6'—C7'—H7A' | 109.9 (11) |
| H7A—C7—H7B | 107.1 (15) | H7B'—C7'—H7A' | 111.1 (16) |
| C9—O8—C7 | 115.32 (11) | C9'—O8'—C7' | 113.82 (10) |
| O3—C9—O8 | 122.56 (13) | O3'—C9'—O8' | 122.16 (12) |
| O3—C9—C9A | 125.70 (13) | O3'—C9'—C9A' | 126.07 (12) |
| O8—C9—C9A | 111.73 (11) | O8'—C9'—C9A' | 111.77 (11) |
| C9—C9A—C1 | 109.41 (11) | C9'—C9A'—C1' | 108.96 (10) |
| C9—C9A—C10 | 107.52 (11) | C9'—C9A'—C10' | 107.36 (11) |
| C1—C9A—C10 | 111.68 (12) | C1'—C9A'—C10' | 111.78 (11) |
| C9—C9A—C4A | 109.27 (11) | C9'—C9A'—C4A' | 110.13 (10) |
| C1—C9A—C4A | 111.30 (11) | C1'—C9A'—C4A' | 111.03 (10) |
| C10—C9A—C4A | 107.54 (11) | C10'—C9A'—C4A' | 107.51 (11) |
| C9A—C10—H10A | 110.0 (13) | C9A'—C10'—H10D | 110.8 (13) |
| C9A—C10—H10B | 108.1 (13) | C9A'—C10'—H10F | 108.6 (13) |
| H10A—C10—H10B | 109.6 (18) | H10D—C10'—H10F | 107.5 (18) |
| C9A—C10—H10C | 111.4 (13) | C9A'—C10'—H10E | 110.3 (13) |
| H10A—C10—H10C | 108.5 (18) | H10D—C10'—H10E | 109.5 (18) |
| H10B—C10—H10C | 109.2 (18) | H10F—C10'—H10E | 110.2 (17) |
