The title racemate, C
11H
16O
3, displays two different hydrogen-bonding modes in the crystal structure. The chosen asymmetric unit consists of two molecules of identical handedness that differ in the rotation of their carboxyl groups and are linked by an acid-to-ketone hydrogen bond [O
O = 2.7219 (17) Å and O—H
O = 174°]. The remaining carboxyl forms a centrosymmetric dimer with a second such unit [O
O = 2.6368 (15) Å and O—H
O = 174°], while the ketones at the extremities of this four-molecule aggregate remain unengaged. Five intermolecular C—H
O close contacts were found.
Supporting information
CCDC reference: 643121
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.106
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
| Author Response: _diffrn_measured_fraction_theta_full Low .......0.91.
(Alert level A). Even though we collected data out to 0.83 \%A,
the crystal diffracted poorly beyond 0.88 \%A resolution, where
more than 40% of the missing data lie. Larger
crystals were not obtainable, and since the crystals of this
compound are no longer available, we can only rely on the current
data set.
|
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 67.85
From the CIF: _diffrn_reflns_theta_full 67.85
From the CIF: _reflns_number_total 3340
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3657
Completeness (_total/calc) 91.33%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 60 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2B - C9B .. 5.52 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 23
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C11 H16 O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C11 H16 O3
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: SHELXL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2004); software used to prepare material for publication: SHELXTL.
(2
S*,4aR*,8aS*)-6-Oxoperhydronaphthalene-2-carboxylic acid
top
Crystal data top
C11H16O3 | Z = 4 |
Mr = 196.24 | F(000) = 424 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
Hall symbol: -P 1 | Melting point: 393 K |
a = 7.4089 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 11.3743 (2) Å | Cell parameters from 10147 reflections |
c = 12.9478 (2) Å | θ = 3.7–67.9° |
α = 112.6743 (6)° | µ = 0.76 mm−1 |
β = 91.9072 (6)° | T = 100 K |
γ = 90.6949 (6)° | Parallelepiped, colourless |
V = 1005.87 (3) Å3 | 0.33 × 0.19 × 0.14 mm |
Data collection top
Bruker SMART CCD APEXII area-detector diffractometer | 3340 independent reflections |
Radiation source: fine-focus sealed tube | 3041 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 67.9°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −8→8 |
Tmin = 0.790, Tmax = 0.901 | k = −13→13 |
10147 measured reflections | l = −15→13 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.6443P] where P = (Fo2 + 2Fc2)/3 |
3340 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
Experimental. crystal mounted on cryoloop using Paratone-N |
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 | |
C1A | 0.0155 (2) | 0.51481 (15) | 0.70850 (14) | 0.0229 (3) | |
H1A | −0.0209 | 0.5964 | 0.7044 | 0.027* | |
H1B | 0.1295 | 0.4897 | 0.6688 | 0.027* | |
O1A | −0.63304 (17) | 0.33432 (12) | 0.49361 (12) | 0.0400 (3) | |
C1B | 1.0437 (2) | 0.92719 (14) | 1.30068 (13) | 0.0213 (3) | |
H1BA | 1.1236 | 0.8634 | 1.2496 | 0.026* | |
H1BB | 1.0122 | 0.8984 | 1.3610 | 0.026* | |
O1B | 0.58059 (14) | 0.82579 (11) | 0.93838 (10) | 0.0257 (3) | |
C2A | 0.0485 (2) | 0.53432 (15) | 0.83160 (14) | 0.0233 (3) | |
H2A | 0.0969 | 0.4530 | 0.8324 | 0.028* | |
O2A | 0.17140 (17) | 0.71947 (12) | 0.98523 (10) | 0.0343 (3) | |
C2B | 1.1449 (2) | 1.05722 (15) | 1.35218 (14) | 0.0217 (3) | |
H2BA | 1.0646 | 1.1197 | 1.4059 | 0.026* | |
O2B | 1.45654 (14) | 1.01194 (11) | 1.37686 (9) | 0.0264 (3) | |
C3A | −0.1272 (2) | 0.55815 (16) | 0.89392 (14) | 0.0268 (4) | |
H3A | −0.1028 | 0.5602 | 0.9702 | 0.032* | |
H3B | −0.1724 | 0.6425 | 0.9014 | 0.032* | |
O3A | 0.33489 (16) | 0.63283 (12) | 0.83407 (10) | 0.0337 (3) | |
H3AA | 0.4069 | 0.6932 | 0.8710 | 0.051* | |
C3B | 1.1915 (2) | 1.10597 (15) | 1.26143 (14) | 0.0235 (4) | |
H3BA | 1.2760 | 1.0475 | 1.2095 | 0.028* | |
H3BB | 1.2514 | 1.1912 | 1.2962 | 0.028* | |
O3B | 1.27197 (15) | 1.04998 (13) | 1.51884 (10) | 0.0309 (3) | |
H3BC | 1.3624 | 1.0286 | 1.5477 | 0.046* | |
C4AA | −0.3057 (2) | 0.44284 (15) | 0.71365 (14) | 0.0242 (4) | |
H4AA | −0.3469 | 0.5269 | 0.7152 | 0.029* | |
C4A | −0.2720 (2) | 0.45675 (16) | 0.83451 (15) | 0.0286 (4) | |
H4A | −0.3857 | 0.4798 | 0.8749 | 0.034* | |
H4B | −0.2340 | 0.3741 | 0.8357 | 0.034* | |
C4BA | 0.9145 (2) | 0.98678 (14) | 1.14553 (13) | 0.0202 (3) | |
H4BC | 0.9930 | 0.9243 | 1.0903 | 0.024* | |
C4B | 1.0175 (2) | 1.11425 (15) | 1.19596 (14) | 0.0233 (4) | |
H4BA | 0.9386 | 1.1789 | 1.2470 | 0.028* | |
H4BB | 1.0493 | 1.1423 | 1.1352 | 0.028* | |
C5A | −0.4562 (2) | 0.34366 (17) | 0.65430 (16) | 0.0313 (4) | |
H5A | −0.4241 | 0.2609 | 0.6577 | 0.038* | |
H5B | −0.5700 | 0.3708 | 0.6938 | 0.038* | |
C5B | 0.7397 (2) | 0.99760 (15) | 1.08311 (14) | 0.0230 (4) | |
H5BA | 0.6644 | 1.0642 | 1.1351 | 0.028* | |
H5BB | 0.7700 | 1.0239 | 1.0211 | 0.028* | |
C6A | −0.4853 (2) | 0.32697 (15) | 0.53375 (16) | 0.0305 (4) | |
C6B | 0.6337 (2) | 0.87311 (15) | 1.03643 (14) | 0.0227 (4) | |
C7A | −0.3169 (2) | 0.30065 (18) | 0.46723 (16) | 0.0350 (4) | |
H7A | −0.3445 | 0.3045 | 0.3933 | 0.042* | |
H7B | −0.2768 | 0.2136 | 0.4544 | 0.042* | |
C7B | 0.5996 (2) | 0.81041 (16) | 1.11719 (14) | 0.0251 (4) | |
H7BA | 0.5519 | 0.7224 | 1.0754 | 0.030* | |
H7BB | 0.5073 | 0.8580 | 1.1698 | 0.030* | |
C8AA | −0.1314 (2) | 0.41249 (15) | 0.64969 (14) | 0.0232 (4) | |
H8AA | −0.0877 | 0.3295 | 0.6494 | 0.028* | |
C8A | −0.1638 (2) | 0.39761 (16) | 0.52846 (15) | 0.0278 (4) | |
H8A | −0.0510 | 0.3700 | 0.4880 | 0.033* | |
H8B | −0.1939 | 0.4815 | 0.5269 | 0.033* | |
C8BA | 0.8718 (2) | 0.93585 (14) | 1.23595 (13) | 0.0203 (3) | |
H8BC | 0.7899 | 0.9968 | 1.2898 | 0.024* | |
C8B | 0.7740 (2) | 0.80643 (15) | 1.18395 (14) | 0.0234 (4) | |
H8BA | 0.7435 | 0.7770 | 1.2441 | 0.028* | |
H8BB | 0.8560 | 0.7440 | 1.1334 | 0.028* | |
C9A | 0.1884 (2) | 0.63848 (15) | 0.89249 (14) | 0.0244 (4) | |
C9B | 1.3076 (2) | 1.03973 (15) | 1.41662 (14) | 0.0225 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0243 (8) | 0.0220 (8) | 0.0230 (9) | −0.0012 (6) | 0.0011 (7) | 0.0094 (7) |
O1A | 0.0311 (7) | 0.0361 (7) | 0.0429 (8) | −0.0016 (6) | −0.0072 (6) | 0.0051 (6) |
C1B | 0.0197 (8) | 0.0223 (8) | 0.0233 (9) | 0.0008 (6) | 0.0016 (6) | 0.0103 (7) |
O1B | 0.0224 (6) | 0.0298 (6) | 0.0228 (7) | −0.0001 (5) | −0.0050 (5) | 0.0082 (5) |
C2A | 0.0259 (8) | 0.0196 (7) | 0.0238 (9) | 0.0028 (6) | −0.0005 (7) | 0.0078 (7) |
O2A | 0.0360 (7) | 0.0332 (7) | 0.0260 (7) | 0.0020 (5) | −0.0001 (6) | 0.0032 (6) |
C2B | 0.0192 (8) | 0.0238 (8) | 0.0221 (9) | −0.0001 (6) | −0.0012 (6) | 0.0091 (7) |
O2B | 0.0181 (6) | 0.0393 (7) | 0.0229 (6) | 0.0033 (5) | −0.0001 (5) | 0.0131 (5) |
C3A | 0.0309 (9) | 0.0283 (8) | 0.0230 (9) | 0.0039 (7) | 0.0035 (7) | 0.0117 (7) |
O3A | 0.0268 (6) | 0.0342 (7) | 0.0287 (7) | −0.0068 (5) | 0.0007 (5) | −0.0003 (6) |
C3B | 0.0209 (8) | 0.0246 (8) | 0.0272 (9) | −0.0042 (6) | −0.0019 (7) | 0.0127 (7) |
O3B | 0.0223 (6) | 0.0522 (8) | 0.0236 (6) | 0.0044 (5) | 0.0002 (5) | 0.0204 (6) |
C4AA | 0.0240 (8) | 0.0210 (8) | 0.0284 (9) | 0.0000 (6) | 0.0036 (7) | 0.0103 (7) |
C4A | 0.0289 (9) | 0.0298 (9) | 0.0299 (10) | 0.0022 (7) | 0.0077 (7) | 0.0142 (8) |
C4BA | 0.0196 (8) | 0.0211 (7) | 0.0207 (8) | 0.0015 (6) | −0.0003 (6) | 0.0091 (7) |
C4B | 0.0247 (8) | 0.0220 (8) | 0.0270 (9) | −0.0001 (6) | 0.0006 (7) | 0.0137 (7) |
C5A | 0.0256 (9) | 0.0274 (9) | 0.0409 (11) | −0.0037 (7) | 0.0049 (8) | 0.0129 (8) |
C5B | 0.0252 (8) | 0.0227 (8) | 0.0233 (9) | 0.0010 (6) | −0.0034 (7) | 0.0116 (7) |
C6A | 0.0288 (9) | 0.0198 (8) | 0.0367 (11) | −0.0074 (7) | −0.0026 (8) | 0.0046 (8) |
C6B | 0.0177 (7) | 0.0252 (8) | 0.0245 (9) | 0.0048 (6) | −0.0011 (7) | 0.0089 (7) |
C7A | 0.0328 (10) | 0.0338 (9) | 0.0303 (10) | −0.0087 (8) | 0.0004 (8) | 0.0040 (8) |
C7B | 0.0228 (8) | 0.0271 (8) | 0.0249 (9) | −0.0058 (7) | −0.0024 (7) | 0.0099 (7) |
C8AA | 0.0252 (8) | 0.0179 (7) | 0.0254 (9) | −0.0021 (6) | 0.0030 (7) | 0.0073 (7) |
C8A | 0.0273 (9) | 0.0284 (8) | 0.0249 (9) | −0.0059 (7) | 0.0009 (7) | 0.0073 (7) |
C8BA | 0.0207 (8) | 0.0214 (7) | 0.0209 (8) | 0.0042 (6) | 0.0040 (6) | 0.0103 (7) |
C8B | 0.0244 (8) | 0.0253 (8) | 0.0225 (9) | −0.0012 (7) | −0.0006 (7) | 0.0116 (7) |
C9A | 0.0275 (8) | 0.0243 (8) | 0.0229 (9) | 0.0051 (7) | −0.0024 (7) | 0.0111 (8) |
C9B | 0.0231 (8) | 0.0203 (7) | 0.0222 (9) | −0.0030 (6) | −0.0014 (7) | 0.0065 (7) |
Geometric parameters (Å, º) top
C1A—C8AA | 1.533 (2) | C4AA—H4AA | 1.0000 |
C1A—C2A | 1.533 (2) | C4A—H4A | 0.9900 |
C1A—H1A | 0.9900 | C4A—H4B | 0.9900 |
C1A—H1B | 0.9900 | C4BA—C4B | 1.523 (2) |
O1A—C6A | 1.214 (2) | C4BA—C8BA | 1.533 (2) |
C1B—C8BA | 1.527 (2) | C4BA—C5B | 1.535 (2) |
C1B—C2B | 1.541 (2) | C4BA—H4BC | 1.0000 |
C1B—H1BA | 0.9900 | C4B—H4BA | 0.9900 |
C1B—H1BB | 0.9900 | C4B—H4BB | 0.9900 |
O1B—C6B | 1.221 (2) | C5A—C6A | 1.506 (3) |
C2A—C9A | 1.515 (2) | C5A—H5A | 0.9900 |
C2A—C3A | 1.526 (2) | C5A—H5B | 0.9900 |
C2A—H2A | 1.0000 | C5B—C6B | 1.507 (2) |
O2A—C9A | 1.211 (2) | C5B—H5BA | 0.9900 |
C2B—C9B | 1.502 (2) | C5B—H5BB | 0.9900 |
C2B—C3B | 1.527 (2) | C6A—C7A | 1.506 (2) |
C2B—H2BA | 1.0000 | C6B—C7B | 1.501 (2) |
O2B—C9B | 1.2261 (19) | C7A—C8A | 1.539 (2) |
C3A—C4A | 1.518 (2) | C7A—H7A | 0.9900 |
C3A—H3A | 0.9900 | C7A—H7B | 0.9900 |
C3A—H3B | 0.9900 | C7B—C8B | 1.542 (2) |
O3A—C9A | 1.332 (2) | C7B—H7BA | 0.9900 |
O3A—H3AA | 0.8400 | C7B—H7BB | 0.9900 |
C3B—C4B | 1.543 (2) | C8AA—C8A | 1.523 (2) |
C3B—H3BA | 0.9900 | C8AA—H8AA | 1.0000 |
C3B—H3BB | 0.9900 | C8A—H8A | 0.9900 |
O3B—C9B | 1.319 (2) | C8A—H8B | 0.9900 |
O3B—H3BC | 0.8400 | C8BA—C8B | 1.524 (2) |
C4AA—C4A | 1.523 (2) | C8BA—H8BC | 1.0000 |
C4AA—C8AA | 1.528 (2) | C8B—H8BA | 0.9900 |
C4AA—C5A | 1.533 (2) | C8B—H8BB | 0.9900 |
| | | |
C8AA—C1A—C2A | 112.20 (13) | H4BA—C4B—H4BB | 107.9 |
C8AA—C1A—H1A | 109.2 | C6A—C5A—C4AA | 111.60 (14) |
C2A—C1A—H1A | 109.2 | C6A—C5A—H5A | 109.3 |
C8AA—C1A—H1B | 109.2 | C4AA—C5A—H5A | 109.3 |
C2A—C1A—H1B | 109.2 | C6A—C5A—H5B | 109.3 |
H1A—C1A—H1B | 107.9 | C4AA—C5A—H5B | 109.3 |
C8BA—C1B—C2B | 111.04 (12) | H5A—C5A—H5B | 108.0 |
C8BA—C1B—H1BA | 109.4 | C6B—C5B—C4BA | 111.60 (12) |
C2B—C1B—H1BA | 109.4 | C6B—C5B—H5BA | 109.3 |
C8BA—C1B—H1BB | 109.4 | C4BA—C5B—H5BA | 109.3 |
C2B—C1B—H1BB | 109.4 | C6B—C5B—H5BB | 109.3 |
H1BA—C1B—H1BB | 108.0 | C4BA—C5B—H5BB | 109.3 |
C9A—C2A—C3A | 110.81 (13) | H5BA—C5B—H5BB | 108.0 |
C9A—C2A—C1A | 113.07 (13) | O1A—C6A—C5A | 122.44 (17) |
C3A—C2A—C1A | 111.49 (13) | O1A—C6A—C7A | 122.78 (18) |
C9A—C2A—H2A | 107.0 | C5A—C6A—C7A | 114.78 (15) |
C3A—C2A—H2A | 107.0 | O1B—C6B—C7B | 122.26 (15) |
C1A—C2A—H2A | 107.0 | O1B—C6B—C5B | 121.72 (14) |
C9B—C2B—C3B | 113.47 (13) | C7B—C6B—C5B | 116.01 (14) |
C9B—C2B—C1B | 106.93 (12) | C6A—C7A—C8A | 111.43 (15) |
C3B—C2B—C1B | 110.74 (13) | C6A—C7A—H7A | 109.3 |
C9B—C2B—H2BA | 108.5 | C8A—C7A—H7A | 109.3 |
C3B—C2B—H2BA | 108.5 | C6A—C7A—H7B | 109.3 |
C1B—C2B—H2BA | 108.5 | C8A—C7A—H7B | 109.3 |
C4A—C3A—C2A | 112.41 (14) | H7A—C7A—H7B | 108.0 |
C4A—C3A—H3A | 109.1 | C6B—C7B—C8B | 111.26 (13) |
C2A—C3A—H3A | 109.1 | C6B—C7B—H7BA | 109.4 |
C4A—C3A—H3B | 109.1 | C8B—C7B—H7BA | 109.4 |
C2A—C3A—H3B | 109.1 | C6B—C7B—H7BB | 109.4 |
H3A—C3A—H3B | 107.9 | C8B—C7B—H7BB | 109.4 |
C9A—O3A—H3AA | 109.5 | H7BA—C7B—H7BB | 108.0 |
C2B—C3B—C4B | 109.73 (12) | C8A—C8AA—C4AA | 111.35 (14) |
C2B—C3B—H3BA | 109.7 | C8A—C8AA—C1A | 110.87 (13) |
C4B—C3B—H3BA | 109.7 | C4AA—C8AA—C1A | 110.75 (13) |
C2B—C3B—H3BB | 109.7 | C8A—C8AA—H8AA | 107.9 |
C4B—C3B—H3BB | 109.7 | C4AA—C8AA—H8AA | 107.9 |
H3BA—C3B—H3BB | 108.2 | C1A—C8AA—H8AA | 107.9 |
C9B—O3B—H3BC | 109.5 | C8AA—C8A—C7A | 112.95 (14) |
C4A—C4AA—C8AA | 110.91 (14) | C8AA—C8A—H8A | 109.0 |
C4A—C4AA—C5A | 111.68 (13) | C7A—C8A—H8A | 109.0 |
C8AA—C4AA—C5A | 111.58 (14) | C8AA—C8A—H8B | 109.0 |
C4A—C4AA—H4AA | 107.5 | C7A—C8A—H8B | 109.0 |
C8AA—C4AA—H4AA | 107.5 | H8A—C8A—H8B | 107.8 |
C5A—C4AA—H4AA | 107.5 | C8B—C8BA—C1B | 110.67 (12) |
C3A—C4A—C4AA | 111.41 (13) | C8B—C8BA—C4BA | 110.51 (13) |
C3A—C4A—H4A | 109.3 | C1B—C8BA—C4BA | 110.87 (12) |
C4AA—C4A—H4A | 109.3 | C8B—C8BA—H8BC | 108.2 |
C3A—C4A—H4B | 109.3 | C1B—C8BA—H8BC | 108.2 |
C4AA—C4A—H4B | 109.3 | C4BA—C8BA—H8BC | 108.2 |
H4A—C4A—H4B | 108.0 | C8BA—C8B—C7B | 112.52 (13) |
C4B—C4BA—C8BA | 111.02 (13) | C8BA—C8B—H8BA | 109.1 |
C4B—C4BA—C5B | 111.20 (12) | C7B—C8B—H8BA | 109.1 |
C8BA—C4BA—C5B | 110.13 (12) | C8BA—C8B—H8BB | 109.1 |
C4B—C4BA—H4BC | 108.1 | C7B—C8B—H8BB | 109.1 |
C8BA—C4BA—H4BC | 108.1 | H8BA—C8B—H8BB | 107.8 |
C5B—C4BA—H4BC | 108.1 | O2A—C9A—O3A | 122.41 (15) |
C4BA—C4B—C3B | 111.95 (12) | O2A—C9A—C2A | 124.21 (15) |
C4BA—C4B—H4BA | 109.2 | O3A—C9A—C2A | 113.37 (14) |
C3B—C4B—H4BA | 109.2 | O2B—C9B—O3B | 123.00 (15) |
C4BA—C4B—H4BB | 109.2 | O2B—C9B—C2B | 123.74 (14) |
C3B—C4B—H4BB | 109.2 | O3B—C9B—C2B | 113.15 (13) |
| | | |
C8AA—C1A—C2A—C9A | −177.89 (13) | C4A—C4AA—C8AA—C8A | 179.66 (13) |
C8AA—C1A—C2A—C3A | −52.26 (17) | C5A—C4AA—C8AA—C8A | 54.47 (17) |
C8BA—C1B—C2B—C9B | 178.25 (12) | C4A—C4AA—C8AA—C1A | −56.49 (17) |
C8BA—C1B—C2B—C3B | −57.67 (16) | C5A—C4AA—C8AA—C1A | 178.32 (13) |
C9A—C2A—C3A—C4A | 179.12 (13) | C2A—C1A—C8AA—C8A | 178.72 (13) |
C1A—C2A—C3A—C4A | 52.24 (17) | C2A—C1A—C8AA—C4AA | 54.59 (17) |
C9B—C2B—C3B—C4B | 177.08 (13) | C4AA—C8AA—C8A—C7A | −53.32 (18) |
C1B—C2B—C3B—C4B | 56.82 (16) | C1A—C8AA—C8A—C7A | −177.10 (14) |
C2A—C3A—C4A—C4AA | −54.78 (18) | C6A—C7A—C8A—C8AA | 50.4 (2) |
C8AA—C4AA—C4A—C3A | 56.74 (17) | C2B—C1B—C8BA—C8B | 179.19 (12) |
C5A—C4AA—C4A—C3A | −178.13 (13) | C2B—C1B—C8BA—C4BA | 56.20 (17) |
C8BA—C4BA—C4B—C3B | 55.67 (17) | C4B—C4BA—C8BA—C8B | −178.23 (12) |
C5B—C4BA—C4B—C3B | 178.66 (13) | C5B—C4BA—C8BA—C8B | 58.16 (16) |
C2B—C3B—C4B—C4BA | −56.48 (17) | C4B—C4BA—C8BA—C1B | −55.15 (16) |
C4A—C4AA—C5A—C6A | −178.16 (14) | C5B—C4BA—C8BA—C1B | −178.76 (12) |
C8AA—C4AA—C5A—C6A | −53.40 (18) | C1B—C8BA—C8B—C7B | −179.76 (13) |
C4B—C4BA—C5B—C6B | −177.98 (13) | C4BA—C8BA—C8B—C7B | −56.56 (17) |
C8BA—C4BA—C5B—C6B | −54.47 (17) | C6B—C7B—C8B—C8BA | 50.10 (18) |
C4AA—C5A—C6A—O1A | −127.84 (17) | C3A—C2A—C9A—O2A | 9.3 (2) |
C4AA—C5A—C6A—C7A | 52.11 (19) | C1A—C2A—C9A—O2A | 135.34 (16) |
C4BA—C5B—C6B—O1B | −128.63 (15) | C3A—C2A—C9A—O3A | −170.88 (13) |
C4BA—C5B—C6B—C7B | 50.60 (18) | C1A—C2A—C9A—O3A | −44.88 (18) |
O1A—C6A—C7A—C8A | 129.77 (18) | C3B—C2B—C9B—O2B | −30.2 (2) |
C5A—C6A—C7A—C8A | −50.2 (2) | C1B—C2B—C9B—O2B | 92.18 (17) |
O1B—C6B—C7B—C8B | 131.63 (15) | C3B—C2B—C9B—O3B | 153.51 (14) |
C5B—C6B—C7B—C8B | −47.59 (18) | C1B—C2B—C9B—O3B | −84.10 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3AA···O1B | 0.84 | 1.89 | 2.7219 (17) | 174 |
O3B—H3BC···O2Bi | 0.84 | 1.80 | 2.6368 (15) | 174 |
C3B—H3BB···O1Aii | 0.99 | 2.56 | 3.333 (2) | 135 |
C8A—H8B···O1Aiii | 0.99 | 2.56 | 3.521 (2) | 163 |
C4BA—H4BC···O2Aiv | 1.00 | 2.60 | 3.565 (2) | 161 |
C5B—H5BA···O1Bv | 0.99 | 2.57 | 3.201 (2) | 121 |
C1B—H1BB···O3Bvi | 0.99 | 2.60 | 3.303 (2) | 128 |
Symmetry codes: (i) −x+3, −y+2, −z+3; (ii) x+2, y+1, z+1; (iii) −x−1, −y+1, −z+1; (iv) x+1, y, z; (v) −x+1, −y+2, −z+2; (vi) −x+2, −y+2, −z+3. |