There are four independent molecules in the asymmetric unit of the title compound, C
7H
10O
3, and two of the molecules are disordered. Molecules form two independent O—H
O hydrogen-bonded dimers, through the carboxyl groups, with O
O distances of 2.669 (3), 2.661 (3), 2.653 (3) and 2.654 (3) Å. Each hydrogen-bonded dimer contains a disordered molecule.
Supporting information
CCDC reference: 206788
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.118
- Data-to-parameter ratio = 8.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.46
From the CIF: _reflns_number_total 3220
Count of symmetry unique reflns 3236
Completeness (_total/calc) 99.51%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
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.
Data collection: COLLECT (Nonius BV, 1997-2002); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2-Hydroxycyclohexene-1-carboxylic acid
top
Crystal data top
C7H10O3 | F(000) = 1216 |
Mr = 142.15 | Dx = 1.336 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 2659 reflections |
a = 11.1360 (4) Å | θ = 2.6–27.5° |
b = 11.1049 (3) Å | µ = 0.10 mm−1 |
c = 22.8774 (9) Å | T = 150 K |
β = 91.9072 (12)° | Block, colourless |
V = 2827.55 (17) Å3 | 0.40 × 0.35 × 0.30 mm |
Z = 16 | |
Data collection top
Nonius KappaCCD diffractometer | 2554 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.5°, θmin = 2.6° |
Detector resolution: 9 pixels mm-1 | h = −14→14 |
φ scans and ω scans with κ offsets | k = −14→14 |
8426 measured reflections | l = −29→29 |
3220 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.052P)2 + 1.6672P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3220 reflections | Δρmax = 0.41 e Å−3 |
400 parameters | Δρmin = −0.20 e Å−3 |
32 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (12) |
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 | Occ. (<1) |
O1A | 0.5025 (2) | 0.4443 (2) | 0.99826 (11) | 0.0384 (6) | |
H1A | 0.4503 | 0.4572 | 0.9716 | 0.058* | |
O2A | 0.3979 (2) | 0.4165 (2) | 0.89731 (11) | 0.0403 (6) | |
O3A | 0.4585 (3) | 0.2646 (2) | 0.84107 (11) | 0.0443 (7) | |
H3A | 0.4025 | 0.2917 | 0.8194 | 0.066* | |
C1A | 0.5592 (3) | 0.2919 (3) | 0.93167 (14) | 0.0327 (7) | |
C2A | 0.5721 (3) | 0.3514 (3) | 0.98299 (14) | 0.0319 (7) | |
C3A | 0.6637 (4) | 0.3198 (3) | 1.02951 (16) | 0.0412 (8) | |
H3AA | 0.7046 | 0.3944 | 1.0430 | 0.049* | |
H3AB | 0.6221 | 0.2853 | 1.0633 | 0.049* | |
C4A | 0.7558 (4) | 0.2324 (5) | 1.01036 (19) | 0.0592 (12) | |
H4AA | 0.8175 | 0.2757 | 0.9884 | 0.071* | |
H4AB | 0.7960 | 0.1955 | 1.0452 | 0.071* | |
C5A | 0.7025 (4) | 0.1365 (4) | 0.9731 (2) | 0.0618 (12) | |
H5AA | 0.6443 | 0.0904 | 0.9960 | 0.074* | |
H5AB | 0.7668 | 0.0804 | 0.9617 | 0.074* | |
C6A | 0.6381 (4) | 0.1853 (4) | 0.91744 (17) | 0.0433 (9) | |
H6AA | 0.6984 | 0.2102 | 0.8890 | 0.052* | |
H6AB | 0.5881 | 0.1208 | 0.8993 | 0.052* | |
C7A | 0.4671 (3) | 0.3288 (3) | 0.88942 (14) | 0.0351 (8) | |
O1B | 0.2544 (2) | −0.2838 (2) | 0.66286 (11) | 0.0400 (6) | |
H1B | 0.2419 | −0.2345 | 0.6898 | 0.060* | |
O2B | 0.2888 (2) | −0.1846 (2) | 0.76381 (11) | 0.0384 (6) | |
O3B | 0.4427 (2) | −0.2498 (3) | 0.82081 (11) | 0.0449 (7) | |
H3B | 0.4164 | −0.1956 | 0.8425 | 0.067* | |
C1B | 0.4111 (3) | −0.3451 (3) | 0.73005 (14) | 0.0328 (7) | |
C2B | 0.3481 (3) | −0.3553 (3) | 0.67850 (15) | 0.0315 (7) | |
C3B | 0.3760 (4) | −0.4448 (3) | 0.63269 (15) | 0.0396 (8) | |
H3BA | 0.4086 | −0.4020 | 0.5987 | 0.048* | |
H3BB | 0.3006 | −0.4850 | 0.6194 | 0.048* | |
C4B | 0.4649 (4) | −0.5396 (4) | 0.65305 (18) | 0.0563 (11) | |
H4BA | 0.4229 | −0.6017 | 0.6757 | 0.068* | |
H4BB | 0.4992 | −0.5792 | 0.6186 | 0.068* | |
C5B | 0.5633 (4) | −0.4871 (4) | 0.6898 (2) | 0.0577 (11) | |
H5BA | 0.6074 | −0.4275 | 0.6665 | 0.069* | |
H5BB | 0.6204 | −0.5517 | 0.7017 | 0.069* | |
C6B | 0.5172 (4) | −0.4254 (3) | 0.74483 (17) | 0.0412 (9) | |
H6BA | 0.4933 | −0.4875 | 0.7732 | 0.049* | |
H6BB | 0.5826 | −0.3768 | 0.7633 | 0.049* | |
C7B | 0.3754 (3) | −0.2552 (3) | 0.77191 (14) | 0.0343 (8) | |
O1C | 0.1713 (2) | 0.3068 (2) | 0.66833 (11) | 0.0423 (6) | |
H1C | 0.2215 | 0.2906 | 0.6955 | 0.063* | |
O2C | 0.2761 (2) | 0.3325 (2) | 0.76997 (11) | 0.0384 (6) | |
O3C | 0.2192 (3) | 0.4868 (2) | 0.82564 (11) | 0.0443 (7) | |
H3C | 0.2743 | 0.4591 | 0.8477 | 0.066* | |
C1C | 0.1165 (3) | 0.4595 (3) | 0.73599 (14) | 0.0317 (7) | |
C2C | 0.1048 (3) | 0.4018 (3) | 0.68371 (14) | 0.0337 (7) | |
C3C | 0.0160 (4) | 0.4388 (3) | 0.63633 (17) | 0.0438 (9) | |
H3CA | −0.0520 | 0.3813 | 0.6351 | 0.053* | 0.762 (7) |
H3CB | 0.0550 | 0.4354 | 0.5981 | 0.053* | 0.762 (7) |
C3C* | 0.0160 (4) | 0.4388 (3) | 0.63633 (17) | 0.0438 (9) | 0.00 |
H3CC | −0.0202 | 0.3655 | 0.6185 | 0.053* | 0.238 (7) |
H3CD | 0.0593 | 0.4817 | 0.6055 | 0.053* | 0.238 (7) |
C4C | −0.0320 (5) | 0.5663 (4) | 0.6461 (2) | 0.0442 (13) | 0.762 (7) |
H4CA | 0.0314 | 0.6260 | 0.6380 | 0.053* | 0.762 (7) |
H4CB | −0.1013 | 0.5817 | 0.6190 | 0.053* | 0.762 (7) |
C5C | −0.0709 (4) | 0.5801 (6) | 0.7092 (2) | 0.0461 (15) | 0.762 (7) |
H5CA | −0.1068 | 0.6607 | 0.7147 | 0.055* | 0.762 (7) |
H5CB | −0.1323 | 0.5187 | 0.7178 | 0.055* | 0.762 (7) |
C4C* | −0.0847 (9) | 0.5200 (14) | 0.6577 (7) | 0.0439 (17) | 0.238 (7) |
H4CC | −0.1286 | 0.5574 | 0.6240 | 0.053* | 0.238 (7) |
H4CD | −0.1423 | 0.4725 | 0.6803 | 0.053* | 0.238 (7) |
C5C* | −0.0255 (17) | 0.6168 (12) | 0.6964 (5) | 0.0454 (19) | 0.238 (7) |
H5CC | 0.0336 | 0.6616 | 0.6733 | 0.054* | 0.238 (7) |
H5CD | −0.0876 | 0.6747 | 0.7085 | 0.054* | 0.238 (7) |
C6C | 0.0380 (4) | 0.5647 (3) | 0.75087 (16) | 0.0388 (9) | |
H6CA | 0.0867 | 0.6392 | 0.7503 | 0.047* | 0.762 (7) |
H6CB | 0.0097 | 0.5540 | 0.7911 | 0.047* | 0.762 (7) |
C6C* | 0.0380 (4) | 0.5647 (3) | 0.75087 (16) | 0.0388 (9) | 0.00 |
H6CC | 0.0878 | 0.6280 | 0.7701 | 0.047* | 0.238 (7) |
H6CD | −0.0228 | 0.5383 | 0.7788 | 0.047* | 0.238 (7) |
C7C | 0.2094 (3) | 0.4203 (3) | 0.77745 (14) | 0.0333 (7) | |
O1D | 0.4100 (2) | 0.0251 (2) | 0.99417 (11) | 0.0418 (6) | |
H1D | 0.4245 | −0.0236 | 0.9672 | 0.063* | |
O2D | 0.3796 (2) | −0.0729 (2) | 0.89199 (11) | 0.0405 (6) | |
O3D | 0.2241 (3) | −0.0106 (2) | 0.83577 (11) | 0.0442 (7) | |
H3D | 0.2506 | −0.0647 | 0.8141 | 0.066* | |
C1D | 0.2553 (3) | 0.0860 (3) | 0.92558 (14) | 0.0308 (7) | |
C2D | 0.3145 (3) | 0.0939 (3) | 0.97808 (14) | 0.0326 (7) | |
C3D | 0.2811 (4) | 0.1792 (4) | 1.02524 (17) | 0.0436 (9) | |
H3DA | 0.3395 | 0.2464 | 1.0271 | 0.052* | 0.661 (6) |
H3DB | 0.2850 | 0.1370 | 1.0634 | 0.052* | 0.661 (6) |
C3D* | 0.2811 (4) | 0.1792 (4) | 1.02524 (17) | 0.0436 (9) | 0.00 |
H3DC | 0.3553 | 0.2128 | 1.0439 | 0.052* | 0.339 (6) |
H3DD | 0.2379 | 0.1345 | 1.0555 | 0.052* | 0.339 (6) |
C4D | 0.1529 (4) | 0.2304 (5) | 1.0141 (2) | 0.0426 (14) | 0.661 (6) |
H4DA | 0.0926 | 0.1670 | 1.0212 | 0.051* | 0.661 (6) |
H4DB | 0.1388 | 0.2978 | 1.0414 | 0.051* | 0.661 (6) |
C5D | 0.1395 (6) | 0.2746 (5) | 0.9512 (2) | 0.0419 (15) | 0.661 (6) |
H5DA | 0.2033 | 0.3339 | 0.9431 | 0.050* | 0.661 (6) |
H5DB | 0.0606 | 0.3143 | 0.9448 | 0.050* | 0.661 (6) |
C5D* | 0.1008 (8) | 0.2264 (11) | 0.9649 (3) | 0.0412 (17) | 0.339 (6) |
H5DC | 0.0415 | 0.2889 | 0.9529 | 0.049* | 0.339 (6) |
H5DD | 0.0590 | 0.1655 | 0.9884 | 0.049* | 0.339 (6) |
C4D* | 0.2010 (9) | 0.2840 (7) | 1.0023 (5) | 0.0419 (17) | 0.339 (6) |
H4DC | 0.1672 | 0.3291 | 1.0353 | 0.050* | 0.339 (6) |
H4DD | 0.2482 | 0.3404 | 0.9786 | 0.050* | 0.339 (6) |
C6D | 0.1496 (3) | 0.1660 (3) | 0.91009 (16) | 0.0378 (8) | |
H6DA | 0.0749 | 0.1179 | 0.9115 | 0.045* | 0.661 (6) |
H6DB | 0.1571 | 0.1953 | 0.8695 | 0.045* | 0.661 (6) |
C6D* | 0.1496 (3) | 0.1660 (3) | 0.91009 (16) | 0.0378 (8) | 0.00 |
H6DC | 0.0852 | 0.1174 | 0.8907 | 0.045* | 0.339 (6) |
H6DD | 0.1745 | 0.2287 | 0.8822 | 0.045* | 0.339 (6) |
C7D | 0.2915 (3) | −0.0040 (3) | 0.88395 (14) | 0.0332 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0465 (14) | 0.0384 (13) | 0.0299 (12) | 0.0081 (12) | −0.0028 (10) | −0.0049 (10) |
O2A | 0.0443 (15) | 0.0430 (14) | 0.0330 (13) | 0.0133 (13) | −0.0054 (11) | −0.0069 (11) |
O3A | 0.0492 (16) | 0.0508 (15) | 0.0322 (14) | 0.0160 (13) | −0.0080 (11) | −0.0128 (11) |
C1A | 0.0352 (18) | 0.0354 (17) | 0.0274 (16) | 0.0049 (15) | 0.0000 (14) | −0.0001 (13) |
C2A | 0.0325 (18) | 0.0316 (16) | 0.0315 (17) | −0.0050 (15) | 0.0020 (14) | 0.0007 (13) |
C3A | 0.048 (2) | 0.0455 (19) | 0.0297 (18) | −0.0004 (18) | −0.0046 (15) | 0.0029 (15) |
C4A | 0.052 (3) | 0.078 (3) | 0.048 (2) | 0.019 (2) | −0.0076 (19) | 0.001 (2) |
C5A | 0.059 (3) | 0.058 (3) | 0.067 (3) | 0.025 (2) | −0.016 (2) | −0.007 (2) |
C6A | 0.040 (2) | 0.047 (2) | 0.043 (2) | 0.0077 (18) | −0.0030 (17) | −0.0047 (17) |
C7A | 0.040 (2) | 0.0352 (17) | 0.0304 (16) | 0.0039 (16) | 0.0004 (14) | −0.0035 (14) |
O1B | 0.0408 (14) | 0.0489 (14) | 0.0298 (11) | 0.0114 (12) | −0.0053 (10) | −0.0009 (10) |
O2B | 0.0404 (15) | 0.0430 (13) | 0.0314 (13) | 0.0129 (12) | −0.0073 (10) | −0.0044 (10) |
O3B | 0.0463 (15) | 0.0552 (16) | 0.0324 (13) | 0.0199 (13) | −0.0102 (11) | −0.0074 (11) |
C1B | 0.0363 (19) | 0.0343 (16) | 0.0276 (16) | 0.0062 (15) | 0.0004 (14) | 0.0006 (13) |
C2B | 0.0325 (18) | 0.0322 (16) | 0.0299 (16) | 0.0008 (15) | 0.0014 (13) | 0.0018 (13) |
C3B | 0.044 (2) | 0.0458 (19) | 0.0294 (17) | 0.0019 (17) | 0.0025 (15) | −0.0026 (15) |
C4B | 0.076 (3) | 0.053 (2) | 0.041 (2) | 0.021 (2) | 0.000 (2) | −0.0079 (18) |
C5B | 0.058 (3) | 0.055 (2) | 0.060 (2) | 0.022 (2) | −0.008 (2) | −0.015 (2) |
C6B | 0.044 (2) | 0.040 (2) | 0.039 (2) | 0.0116 (18) | −0.0068 (16) | −0.0019 (16) |
C7B | 0.0353 (19) | 0.0372 (17) | 0.0300 (17) | 0.0014 (16) | −0.0034 (14) | 0.0017 (13) |
O1C | 0.0465 (15) | 0.0428 (14) | 0.0371 (13) | 0.0115 (12) | −0.0081 (11) | −0.0127 (11) |
O2C | 0.0445 (14) | 0.0380 (13) | 0.0321 (13) | 0.0119 (13) | −0.0069 (11) | −0.0079 (11) |
O3C | 0.0568 (18) | 0.0471 (14) | 0.0282 (12) | 0.0202 (13) | −0.0109 (11) | −0.0106 (11) |
C1C | 0.0347 (18) | 0.0301 (16) | 0.0303 (17) | 0.0023 (15) | 0.0002 (14) | −0.0024 (13) |
C2C | 0.0346 (19) | 0.0356 (17) | 0.0308 (16) | 0.0026 (15) | −0.0003 (14) | −0.0024 (14) |
C3C | 0.044 (2) | 0.051 (2) | 0.0354 (19) | 0.0043 (18) | −0.0107 (16) | −0.0040 (16) |
C3C* | 0.044 (2) | 0.051 (2) | 0.0354 (19) | 0.0043 (18) | −0.0107 (16) | −0.0040 (16) |
C4C | 0.047 (3) | 0.044 (3) | 0.040 (3) | 0.007 (2) | −0.012 (2) | −0.002 (2) |
C5C | 0.045 (3) | 0.042 (3) | 0.051 (3) | 0.016 (3) | −0.010 (2) | −0.007 (2) |
C4C* | 0.046 (4) | 0.045 (4) | 0.040 (3) | 0.007 (3) | −0.012 (3) | −0.002 (3) |
C5C* | 0.044 (4) | 0.041 (4) | 0.050 (3) | 0.015 (3) | −0.010 (3) | −0.006 (3) |
C6C | 0.038 (2) | 0.0384 (19) | 0.039 (2) | 0.0094 (17) | −0.0049 (16) | −0.0032 (15) |
C6C* | 0.038 (2) | 0.0384 (19) | 0.039 (2) | 0.0094 (17) | −0.0049 (16) | −0.0032 (15) |
C7C | 0.0389 (19) | 0.0335 (16) | 0.0275 (16) | 0.0032 (16) | 0.0024 (14) | −0.0013 (13) |
O1D | 0.0423 (14) | 0.0446 (14) | 0.0377 (14) | 0.0116 (12) | −0.0112 (11) | −0.0059 (11) |
O2D | 0.0375 (15) | 0.0477 (14) | 0.0359 (14) | 0.0126 (13) | −0.0064 (11) | −0.0068 (11) |
O3D | 0.0510 (16) | 0.0511 (15) | 0.0296 (13) | 0.0181 (13) | −0.0120 (11) | −0.0099 (11) |
C1D | 0.0315 (17) | 0.0321 (16) | 0.0286 (16) | 0.0010 (15) | −0.0019 (13) | −0.0017 (13) |
C2D | 0.0336 (19) | 0.0332 (16) | 0.0305 (17) | 0.0029 (14) | −0.0040 (14) | 0.0006 (13) |
C3D | 0.047 (2) | 0.046 (2) | 0.0374 (19) | 0.0060 (18) | −0.0064 (16) | −0.0092 (16) |
C3D* | 0.047 (2) | 0.046 (2) | 0.0374 (19) | 0.0060 (18) | −0.0064 (16) | −0.0092 (16) |
C4D | 0.047 (4) | 0.037 (3) | 0.044 (3) | 0.010 (3) | 0.001 (3) | −0.009 (2) |
C5D | 0.044 (4) | 0.034 (3) | 0.047 (3) | 0.014 (3) | −0.006 (3) | −0.006 (2) |
C5D* | 0.045 (4) | 0.032 (4) | 0.046 (4) | 0.013 (3) | −0.006 (3) | −0.005 (3) |
C4D* | 0.047 (4) | 0.035 (4) | 0.044 (3) | 0.010 (3) | 0.001 (3) | −0.008 (3) |
C6D | 0.036 (2) | 0.0425 (19) | 0.0340 (18) | 0.0085 (17) | −0.0039 (15) | −0.0030 (15) |
C6D* | 0.036 (2) | 0.0425 (19) | 0.0340 (18) | 0.0085 (17) | −0.0039 (15) | −0.0030 (15) |
C7D | 0.0325 (18) | 0.0389 (17) | 0.0279 (16) | 0.0054 (15) | −0.0030 (13) | −0.0027 (14) |
Geometric parameters (Å, º) top
O1A—C2A | 1.344 (4) | C1C—C2C | 1.359 (4) |
O1A—H1A | 0.8400 | C1C—C7C | 1.447 (5) |
O2A—C7A | 1.259 (4) | C1C—C6C | 1.505 (5) |
O3A—C7A | 1.317 (4) | C2C—C3C | 1.500 (5) |
O3A—H3A | 0.8400 | C3C—C4C | 1.533 (6) |
C1A—C2A | 1.350 (4) | C3C—H3CA | 0.9900 |
C1A—C7A | 1.445 (5) | C3C—H3CB | 0.9900 |
C1A—C6A | 1.516 (5) | C4C—C5C | 1.528 (6) |
C2A—C3A | 1.491 (5) | C4C—H4CA | 0.9900 |
C3A—C4A | 1.489 (6) | C4C—H4CB | 0.9900 |
C3A—H3AA | 0.9900 | C5C—C6C | 1.527 (6) |
C3A—H3AB | 0.9900 | C5C—H5CA | 0.9900 |
C4A—C5A | 1.476 (6) | C5C—H5CB | 0.9900 |
C4A—H4AA | 0.9900 | C4C*—C5C* | 1.528 (6) |
C4A—H4AB | 0.9900 | C4C*—H4CC | 0.9900 |
C5A—C6A | 1.539 (6) | C4C*—H4CD | 0.9900 |
C5A—H5AA | 0.9900 | C5C*—H5CC | 0.9900 |
C5A—H5AB | 0.9900 | C5C*—H5CD | 0.9900 |
C6A—H6AA | 0.9900 | C6C—H6CA | 0.9900 |
C6A—H6AB | 0.9900 | C6C—H6CB | 0.9900 |
O1B—C2B | 1.349 (4) | O1D—C2D | 1.350 (4) |
O1B—H1B | 0.8400 | O1D—H1D | 0.8400 |
O2B—C7B | 1.251 (4) | O2D—C7D | 1.253 (4) |
O3B—C7B | 1.327 (4) | O3D—C7D | 1.314 (4) |
O3B—H3B | 0.8400 | O3D—H3D | 0.8400 |
C1B—C2B | 1.357 (5) | C1D—C2D | 1.353 (4) |
C1B—C7B | 1.448 (5) | C1D—C7D | 1.448 (4) |
C1B—C6B | 1.511 (5) | C1D—C6D | 1.507 (5) |
C2B—C3B | 1.485 (5) | C2D—C3D | 1.492 (5) |
C3B—C4B | 1.508 (6) | C3D—C4D | 1.550 (6) |
C3B—H3BA | 0.9900 | C3D—H3DA | 0.9900 |
C3B—H3BB | 0.9900 | C3D—H3DB | 0.9900 |
C4B—C5B | 1.479 (6) | C4D—C5D | 1.524 (6) |
C4B—H4BA | 0.9900 | C4D—H4DA | 0.9900 |
C4B—H4BB | 0.9900 | C4D—H4DB | 0.9900 |
C5B—C6B | 1.536 (6) | C5D—C6D | 1.536 (5) |
C5B—H5BA | 0.9900 | C5D—H5DA | 0.9900 |
C5B—H5BB | 0.9900 | C5D—H5DB | 0.9900 |
C6B—H6BA | 0.9900 | C5D*—C4D* | 1.524 (6) |
C6B—H6BB | 0.9900 | C5D*—H5DC | 0.9900 |
O1C—C2C | 1.343 (4) | C5D*—H5DD | 0.9900 |
O1C—H1C | 0.8400 | C4D*—H4DC | 0.9900 |
O2C—C7C | 1.241 (4) | C4D*—H4DD | 0.9900 |
O3C—C7C | 1.328 (4) | C6D—H6DA | 0.9900 |
O3C—H3C | 0.8400 | C6D—H6DB | 0.9900 |
| | | |
C2A—O1A—H1A | 109.5 | O1C—C2C—C3C | 112.4 (3) |
C7A—O3A—H3A | 109.5 | C1C—C2C—C3C | 123.3 (3) |
C2A—C1A—C7A | 119.7 (3) | C2C—C3C—C4C | 111.8 (3) |
C2A—C1A—C6A | 121.5 (3) | C2C—C3C—H3CA | 109.3 |
C7A—C1A—C6A | 118.8 (3) | C4C—C3C—H3CA | 109.3 |
O1A—C2A—C1A | 123.7 (3) | C2C—C3C—H3CB | 109.3 |
O1A—C2A—C3A | 112.5 (3) | C4C—C3C—H3CB | 109.3 |
C1A—C2A—C3A | 123.8 (3) | H3CA—C3C—H3CB | 107.9 |
C4A—C3A—C2A | 113.9 (3) | C5C—C4C—C3C | 110.0 (4) |
C4A—C3A—H3AA | 108.8 | C5C—C4C—H4CA | 109.7 |
C2A—C3A—H3AA | 108.8 | C3C—C4C—H4CA | 109.7 |
C4A—C3A—H3AB | 108.8 | C5C—C4C—H4CB | 109.7 |
C2A—C3A—H3AB | 108.8 | C3C—C4C—H4CB | 109.7 |
H3AA—C3A—H3AB | 107.7 | H4CA—C4C—H4CB | 108.2 |
C5A—C4A—C3A | 111.8 (4) | C6C—C5C—C4C | 109.5 (4) |
C5A—C4A—H4AA | 109.2 | C6C—C5C—H5CA | 109.8 |
C3A—C4A—H4AA | 109.2 | C4C—C5C—H5CA | 109.8 |
C5A—C4A—H4AB | 109.2 | C6C—C5C—H5CB | 109.8 |
C3A—C4A—H4AB | 109.2 | C4C—C5C—H5CB | 109.8 |
H4AA—C4A—H4AB | 107.9 | H5CA—C5C—H5CB | 108.2 |
C4A—C5A—C6A | 113.1 (4) | C5C*—C4C*—H4CC | 110.3 |
C4A—C5A—H5AA | 109.0 | C5C*—C4C*—H4CD | 110.3 |
C6A—C5A—H5AA | 109.0 | H4CC—C4C*—H4CD | 108.6 |
C4A—C5A—H5AB | 109.0 | C4C*—C5C*—H5CC | 109.1 |
C6A—C5A—H5AB | 109.0 | C4C*—C5C*—H5CD | 109.1 |
H5AA—C5A—H5AB | 107.8 | H5CC—C5C*—H5CD | 107.8 |
C1A—C6A—C5A | 110.8 (3) | C1C—C6C—C5C | 113.7 (3) |
C1A—C6A—H6AA | 109.5 | C1C—C6C—H6CA | 108.8 |
C5A—C6A—H6AA | 109.5 | C5C—C6C—H6CA | 108.8 |
C1A—C6A—H6AB | 109.5 | C1C—C6C—H6CB | 108.8 |
C5A—C6A—H6AB | 109.5 | C5C—C6C—H6CB | 108.8 |
H6AA—C6A—H6AB | 108.1 | H6CA—C6C—H6CB | 107.7 |
O2A—C7A—O3A | 120.8 (3) | O2C—C7C—O3C | 121.2 (3) |
O2A—C7A—C1A | 123.2 (3) | O2C—C7C—C1C | 124.3 (3) |
O3A—C7A—C1A | 116.0 (3) | O3C—C7C—C1C | 114.5 (3) |
C2B—O1B—H1B | 109.5 | C2D—O1D—H1D | 109.5 |
C7B—O3B—H3B | 109.5 | C7D—O3D—H3D | 109.5 |
C2B—C1B—C7B | 119.2 (3) | C2D—C1D—C7D | 119.4 (3) |
C2B—C1B—C6B | 121.6 (3) | C2D—C1D—C6D | 121.6 (3) |
C7B—C1B—C6B | 119.3 (3) | C7D—C1D—C6D | 119.0 (3) |
O1B—C2B—C1B | 123.7 (3) | O1D—C2D—C1D | 124.2 (3) |
O1B—C2B—C3B | 112.6 (3) | O1D—C2D—C3D | 112.0 (3) |
C1B—C2B—C3B | 123.7 (3) | C1D—C2D—C3D | 123.8 (3) |
C2B—C3B—C4B | 113.6 (3) | C2D—C3D—C4D | 111.4 (3) |
C2B—C3B—H3BA | 108.8 | C2D—C3D—H3DA | 109.4 |
C4B—C3B—H3BA | 108.8 | C4D—C3D—H3DA | 109.4 |
C2B—C3B—H3BB | 108.8 | C2D—C3D—H3DB | 109.4 |
C4B—C3B—H3BB | 108.8 | C4D—C3D—H3DB | 109.4 |
H3BA—C3B—H3BB | 107.7 | H3DA—C3D—H3DB | 108.0 |
C5B—C4B—C3B | 111.6 (3) | C5D—C4D—C3D | 109.5 (4) |
C5B—C4B—H4BA | 109.3 | C5D—C4D—H4DA | 109.8 |
C3B—C4B—H4BA | 109.3 | C3D—C4D—H4DA | 109.8 |
C5B—C4B—H4BB | 109.3 | C5D—C4D—H4DB | 109.8 |
C3B—C4B—H4BB | 109.3 | C3D—C4D—H4DB | 109.8 |
H4BA—C4B—H4BB | 108.0 | H4DA—C4D—H4DB | 108.2 |
C4B—C5B—C6B | 112.3 (4) | C4D—C5D—C6D | 108.6 (4) |
C4B—C5B—H5BA | 109.1 | C4D—C5D—H5DA | 110.0 |
C6B—C5B—H5BA | 109.1 | C6D—C5D—H5DA | 110.0 |
C4B—C5B—H5BB | 109.1 | C4D—C5D—H5DB | 110.0 |
C6B—C5B—H5BB | 109.1 | C6D—C5D—H5DB | 110.0 |
H5BA—C5B—H5BB | 107.9 | H5DA—C5D—H5DB | 108.4 |
C1B—C6B—C5B | 111.1 (3) | C4D*—C5D*—H5DC | 109.3 |
C1B—C6B—H6BA | 109.4 | C4D*—C5D*—H5DD | 109.3 |
C5B—C6B—H6BA | 109.4 | H5DC—C5D*—H5DD | 108.0 |
C1B—C6B—H6BB | 109.4 | C5D*—C4D*—H4DC | 110.5 |
C5B—C6B—H6BB | 109.4 | C5D*—C4D*—H4DD | 110.5 |
H6BA—C6B—H6BB | 108.0 | H4DC—C4D*—H4DD | 108.7 |
O2B—C7B—O3B | 120.5 (3) | C1D—C6D—C5D | 113.0 (4) |
O2B—C7B—C1B | 124.1 (3) | C1D—C6D—H6DA | 109.0 |
O3B—C7B—C1B | 115.4 (3) | C5D—C6D—H6DA | 109.0 |
C2C—O1C—H1C | 109.5 | C1D—C6D—H6DB | 109.0 |
C7C—O3C—H3C | 109.5 | C5D—C6D—H6DB | 109.0 |
C2C—C1C—C7C | 118.7 (3) | H6DA—C6D—H6DB | 107.8 |
C2C—C1C—C6C | 121.7 (3) | O2D—C7D—O3D | 120.8 (3) |
C7C—C1C—C6C | 119.6 (3) | O2D—C7D—C1D | 124.0 (3) |
O1C—C2C—C1C | 124.3 (3) | O3D—C7D—C1D | 115.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2A | 0.84 | 1.84 | 2.570 (3) | 145 |
O3A—H3A···O2C | 0.84 | 1.83 | 2.669 (3) | 173 |
O1B—H1B···O2B | 0.84 | 1.84 | 2.576 (3) | 145 |
O3B—H3B···O2D | 0.84 | 1.83 | 2.661 (3) | 173 |
O1C—H1C···O2C | 0.84 | 1.85 | 2.582 (3) | 145 |
O3C—H3C···O2A | 0.84 | 1.82 | 2.653 (3) | 174 |
O1D—H1D···O2D | 0.84 | 1.86 | 2.591 (3) | 145 |
O3D—H3D···O2B | 0.84 | 1.82 | 2.654 (3) | 173 |