The title compound, C
20H
32O
5.H
2O, crystallizes in the non-centrosymmetric space group
C2. The molecular skeleton consists of an irregular 14-membered ring and a nearly twist–boat seven-membered γ-lactone ring with a
trans connection. In the solid-state structure, cembradienolide and water molecules form an
R22(7) motif through O—H
O
W and O
W—H
O hydrogen bonds, while adjacent molecules form an infinite chain, described by graph-set motif
C22(12), along the
c axis
via O—H
O hydrogen bonds.
Supporting information
CCDC reference: 251743
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.111
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D H2 .. H2C .. 1.83 Ang.
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 48.00 A 3
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 27.19
From the CIF: _reflns_number_total 2451
Count of symmetry unique reflns 2485
Completeness (_total/calc) 98.63%
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
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 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
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
(1
R*,4
R*,5
S*,12
S*,13
R*)-9-Acetoxycembra-8(E),15 (17)-dien-16,4-olide monohydrate
top
Crystal data top
C20H32O5·H2O | F(000) = 808 |
Mr = 370.47 | Dx = 1.161 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 990 reflections |
a = 15.6359 (17) Å | θ = 2.6–26.9° |
b = 12.1299 (17) Å | µ = 0.08 mm−1 |
c = 11.5236 (14) Å | T = 293 K |
β = 104.111 (3)° | Block, colorless |
V = 2119.6 (5) Å3 | 0.50 × 0.50 × 0.48 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 2451 independent reflections |
Radiation source: fine-focus sealed tube | 2072 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.2°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→19 |
Tmin = 0.959, Tmax = 0.961 | k = −15→15 |
9058 measured reflections | l = −14→14 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0547P)2 + 0.3649P] where P = (Fo2 + 2Fc2)/3 |
2451 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.12 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. All H atoms were placed in calculated positions and refined as
riding atoms. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.22465 (19) | −0.08579 (17) | 0.86221 (19) | 0.0926 (7) | |
H1 | 0.2199 | −0.0490 | 0.9200 | 0.139* | |
O2 | 0.30102 (14) | 0.52143 (17) | 0.94647 (13) | 0.0746 (5) | |
H2 | 0.2721 | 0.5771 | 0.9234 | 0.112* | |
O3 | 0.20161 (13) | 0.54837 (16) | 0.70284 (15) | 0.0696 (5) | |
H3 | 0.2283 | 0.5825 | 0.6613 | 0.104* | |
O4 | 0.21627 (18) | 0.1742 (2) | 0.43955 (16) | 0.1004 (8) | |
O5 | 0.21469 (13) | 0.06120 (16) | 0.58338 (15) | 0.0724 (5) | |
C1 | 0.18333 (13) | 0.2531 (2) | 0.72674 (16) | 0.0485 (4) | |
H1A | 0.2439 | 0.2258 | 0.7532 | 0.058* | |
C2 | 0.12414 (16) | 0.1740 (2) | 0.7756 (2) | 0.0616 (6) | |
H2A | 0.1534 | 0.1552 | 0.8575 | 0.074* | |
H2B | 0.0697 | 0.2118 | 0.7770 | 0.074* | |
C3 | 0.10160 (17) | 0.0679 (2) | 0.7042 (3) | 0.0703 (7) | |
H3A | 0.0726 | 0.0191 | 0.7493 | 0.084* | |
H3B | 0.0588 | 0.0859 | 0.6304 | 0.084* | |
C4 | 0.17570 (18) | 0.0036 (2) | 0.6714 (2) | 0.0647 (6) | |
C5 | 0.25415 (18) | −0.0172 (2) | 0.7795 (2) | 0.0660 (6) | |
H5 | 0.2728 | 0.0536 | 0.8184 | 0.079* | |
C6 | 0.3337 (2) | −0.0709 (3) | 0.7479 (3) | 0.0844 (9) | |
H6A | 0.3283 | −0.0631 | 0.6626 | 0.101* | |
H6B | 0.3338 | −0.1491 | 0.7658 | 0.101* | |
C7 | 0.4216 (2) | −0.0203 (3) | 0.8162 (3) | 0.0946 (11) | |
H7A | 0.4246 | −0.0221 | 0.9013 | 0.114* | |
H7B | 0.4697 | −0.0646 | 0.8023 | 0.114* | |
C8 | 0.43255 (18) | 0.0959 (3) | 0.7794 (3) | 0.0833 (9) | |
C9 | 0.42468 (18) | 0.1809 (3) | 0.8494 (3) | 0.0776 (8) | |
H9 | 0.4197 | 0.1631 | 0.9260 | 0.093* | |
C10 | 0.42277 (18) | 0.3009 (3) | 0.8203 (3) | 0.0762 (8) | |
H10A | 0.3926 | 0.3117 | 0.7370 | 0.091* | |
H10B | 0.4827 | 0.3278 | 0.8317 | 0.091* | |
C11 | 0.37570 (17) | 0.3668 (3) | 0.8997 (2) | 0.0675 (6) | |
H11A | 0.3321 | 0.3190 | 0.9209 | 0.081* | |
H11B | 0.4187 | 0.3850 | 0.9732 | 0.081* | |
C12 | 0.32965 (16) | 0.4730 (2) | 0.84819 (18) | 0.0611 (6) | |
C13 | 0.24814 (15) | 0.4492 (2) | 0.74479 (18) | 0.0532 (5) | |
H13 | 0.2688 | 0.4170 | 0.6785 | 0.064* | |
C14 | 0.18172 (15) | 0.3693 (2) | 0.77715 (19) | 0.0543 (5) | |
H14A | 0.1934 | 0.3645 | 0.8636 | 0.065* | |
H14B | 0.1229 | 0.3995 | 0.7481 | 0.065* | |
C15 | 0.19602 (17) | 0.1595 (2) | 0.53340 (19) | 0.0624 (6) | |
C16 | 0.15829 (13) | 0.2496 (2) | 0.59139 (18) | 0.0543 (5) | |
C17 | 0.10737 (17) | 0.3228 (3) | 0.5219 (2) | 0.0731 (7) | |
H17A | 0.0963 | 0.3166 | 0.4392 | 0.088* | |
H17B | 0.0827 | 0.3804 | 0.5559 | 0.088* | |
C18 | 0.1410 (3) | −0.1033 (3) | 0.6080 (3) | 0.0896 (9) | |
H18A | 0.0956 | −0.0870 | 0.5376 | 0.134* | |
H18B | 0.1173 | −0.1488 | 0.6607 | 0.134* | |
H18C | 0.1883 | −0.1416 | 0.5857 | 0.134* | |
C19 | 0.4488 (2) | 0.1123 (4) | 0.6565 (3) | 0.1026 (12) | |
H19A | 0.4513 | 0.1898 | 0.6405 | 0.154* | |
H19B | 0.4016 | 0.0793 | 0.5975 | 0.154* | |
H19C | 0.5036 | 0.0784 | 0.6534 | 0.154* | |
C20 | 0.3923 (2) | 0.5527 (3) | 0.8094 (3) | 0.0857 (9) | |
H20A | 0.3654 | 0.6242 | 0.7960 | 0.129* | |
H20B | 0.4051 | 0.5266 | 0.7368 | 0.129* | |
H20C | 0.4460 | 0.5576 | 0.8710 | 0.129* | |
O1W | 0.3155 (2) | 0.1946 (2) | 0.1124 (2) | 0.1120 (9) | |
H1B | 0.3190 | 0.261 | 0.130 | 0.134* | |
H2C | 0.3173 | 0.1551 | 0.1748 | 0.134* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.171 (2) | 0.0559 (11) | 0.0650 (11) | 0.0030 (13) | 0.0568 (14) | 0.0022 (9) |
O2 | 0.1244 (14) | 0.0627 (11) | 0.0411 (7) | 0.0036 (10) | 0.0286 (8) | −0.0052 (7) |
O3 | 0.0904 (11) | 0.0648 (11) | 0.0574 (9) | 0.0062 (9) | 0.0252 (8) | 0.0137 (8) |
O4 | 0.181 (2) | 0.0840 (15) | 0.0522 (9) | 0.0047 (15) | 0.0588 (12) | −0.0037 (10) |
O5 | 0.0993 (12) | 0.0689 (12) | 0.0610 (9) | 0.0063 (10) | 0.0429 (9) | 0.0045 (9) |
C1 | 0.0521 (10) | 0.0582 (12) | 0.0396 (9) | 0.0036 (9) | 0.0196 (7) | 0.0018 (9) |
C2 | 0.0718 (13) | 0.0616 (14) | 0.0620 (12) | 0.0034 (12) | 0.0366 (10) | 0.0061 (11) |
C3 | 0.0760 (15) | 0.0659 (16) | 0.0788 (16) | −0.0106 (13) | 0.0379 (12) | 0.0036 (13) |
C4 | 0.0829 (15) | 0.0592 (14) | 0.0600 (13) | −0.0072 (12) | 0.0331 (11) | −0.0015 (11) |
C5 | 0.0992 (18) | 0.0506 (13) | 0.0558 (12) | 0.0063 (12) | 0.0333 (12) | −0.0018 (11) |
C6 | 0.108 (2) | 0.0676 (18) | 0.0827 (18) | 0.0226 (16) | 0.0325 (16) | −0.0076 (15) |
C7 | 0.095 (2) | 0.095 (2) | 0.091 (2) | 0.0433 (19) | 0.0168 (17) | −0.0051 (19) |
C8 | 0.0637 (15) | 0.100 (2) | 0.0833 (18) | 0.0210 (15) | 0.0119 (13) | −0.0135 (17) |
C9 | 0.0673 (14) | 0.095 (2) | 0.0636 (14) | 0.0171 (15) | 0.0029 (11) | −0.0073 (15) |
C10 | 0.0631 (14) | 0.097 (2) | 0.0687 (16) | 0.0040 (15) | 0.0152 (12) | −0.0116 (15) |
C11 | 0.0723 (14) | 0.0793 (17) | 0.0479 (11) | 0.0017 (13) | 0.0092 (10) | −0.0069 (12) |
C12 | 0.0766 (14) | 0.0672 (15) | 0.0422 (10) | −0.0044 (12) | 0.0199 (10) | −0.0049 (10) |
C13 | 0.0690 (13) | 0.0577 (13) | 0.0383 (9) | −0.0006 (10) | 0.0235 (8) | −0.0011 (9) |
C14 | 0.0612 (12) | 0.0604 (14) | 0.0474 (10) | 0.0050 (10) | 0.0249 (9) | −0.0001 (10) |
C15 | 0.0810 (14) | 0.0676 (15) | 0.0400 (10) | −0.0095 (12) | 0.0175 (9) | −0.0055 (10) |
C16 | 0.0566 (11) | 0.0662 (14) | 0.0415 (9) | −0.0055 (11) | 0.0151 (8) | 0.0023 (10) |
C17 | 0.0718 (14) | 0.090 (2) | 0.0555 (13) | 0.0004 (14) | 0.0126 (11) | 0.0122 (13) |
C18 | 0.115 (2) | 0.075 (2) | 0.0814 (19) | −0.0171 (18) | 0.0288 (17) | −0.0170 (16) |
C19 | 0.103 (2) | 0.110 (3) | 0.107 (3) | 0.004 (2) | 0.050 (2) | −0.024 (2) |
C20 | 0.0873 (18) | 0.099 (2) | 0.0697 (15) | −0.0284 (18) | 0.0169 (13) | −0.0042 (17) |
O1W | 0.185 (3) | 0.0633 (13) | 0.1015 (18) | −0.0125 (16) | 0.0613 (18) | −0.0026 (13) |
Geometric parameters (Å, º) top
O1—C5 | 1.423 (3) | C8—C19 | 1.511 (5) |
O1—H1 | 0.8200 | C9—C10 | 1.493 (5) |
O2—C12 | 1.441 (3) | C9—H9 | 0.9300 |
O2—H2 | 0.8200 | C10—C11 | 1.532 (4) |
O3—C13 | 1.428 (3) | C10—H10A | 0.9700 |
O3—H3 | 0.8200 | C10—H10B | 0.9700 |
O4—C15 | 1.212 (3) | C11—C12 | 1.524 (4) |
O5—C15 | 1.325 (3) | C11—H11A | 0.9700 |
O5—C4 | 1.480 (3) | C11—H11B | 0.9700 |
C1—C16 | 1.513 (3) | C12—C20 | 1.518 (4) |
C1—C14 | 1.527 (3) | C12—C13 | 1.545 (3) |
C1—C2 | 1.533 (3) | C13—C14 | 1.532 (3) |
C1—H1A | 0.9800 | C13—H13 | 0.9800 |
C2—C3 | 1.521 (4) | C14—H14A | 0.9700 |
C2—H2A | 0.9700 | C14—H14B | 0.9700 |
C2—H2B | 0.9700 | C15—C16 | 1.477 (4) |
C3—C4 | 1.519 (4) | C16—C17 | 1.324 (4) |
C3—H3A | 0.9700 | C17—H17A | 0.9300 |
C3—H3B | 0.9700 | C17—H17B | 0.9300 |
C4—C18 | 1.522 (4) | C18—H18A | 0.9600 |
C4—C5 | 1.541 (4) | C18—H18B | 0.9600 |
C5—C6 | 1.525 (4) | C18—H18C | 0.9600 |
C5—H5 | 0.9800 | C19—H19A | 0.9600 |
C6—C7 | 1.536 (5) | C19—H19B | 0.9600 |
C6—H6A | 0.9700 | C19—H19C | 0.9600 |
C6—H6B | 0.9700 | C20—H20A | 0.9600 |
C7—C8 | 1.494 (6) | C20—H20B | 0.9600 |
C7—H7A | 0.9700 | C20—H20C | 0.9600 |
C7—H7B | 0.9700 | O1W—H1B | 0.83 |
C8—C9 | 1.332 (5) | O1W—H2C | 0.8596 |
| | | |
C5—O1—H1 | 109.5 | C9—C10—H10B | 109.4 |
C12—O2—H2 | 109.5 | C11—C10—H10B | 109.4 |
C13—O3—H3 | 109.5 | H10A—C10—H10B | 108.0 |
C15—O5—C4 | 129.7 (2) | C12—C11—C10 | 117.3 (2) |
C16—C1—C14 | 113.21 (19) | C12—C11—H11A | 108.0 |
C16—C1—C2 | 109.46 (19) | C10—C11—H11A | 108.0 |
C14—C1—C2 | 111.78 (16) | C12—C11—H11B | 108.0 |
C16—C1—H1A | 107.4 | C10—C11—H11B | 108.0 |
C14—C1—H1A | 107.4 | H11A—C11—H11B | 107.2 |
C2—C1—H1A | 107.4 | O2—C12—C20 | 108.6 (2) |
C3—C2—C1 | 114.32 (17) | O2—C12—C11 | 104.25 (18) |
C3—C2—H2A | 108.7 | C20—C12—C11 | 112.0 (2) |
C1—C2—H2A | 108.7 | O2—C12—C13 | 109.06 (19) |
C3—C2—H2B | 108.7 | C20—C12—C13 | 111.2 (2) |
C1—C2—H2B | 108.7 | C11—C12—C13 | 111.4 (2) |
H2A—C2—H2B | 107.6 | O3—C13—C14 | 107.21 (18) |
C4—C3—C2 | 118.6 (2) | O3—C13—C12 | 111.1 (2) |
C4—C3—H3A | 107.7 | C14—C13—C12 | 114.29 (18) |
C2—C3—H3A | 107.7 | O3—C13—H13 | 108.0 |
C4—C3—H3B | 107.7 | C14—C13—H13 | 108.0 |
C2—C3—H3B | 107.7 | C12—C13—H13 | 108.0 |
H3A—C3—H3B | 107.1 | C1—C14—C13 | 114.61 (16) |
O5—C4—C3 | 113.2 (2) | C1—C14—H14A | 108.6 |
O5—C4—C18 | 103.4 (2) | C13—C14—H14A | 108.6 |
C3—C4—C18 | 110.7 (2) | C1—C14—H14B | 108.6 |
O5—C4—C5 | 104.6 (2) | C13—C14—H14B | 108.6 |
C3—C4—C5 | 112.8 (2) | H14A—C14—H14B | 107.6 |
C18—C4—C5 | 111.6 (2) | O4—C15—O5 | 116.3 (3) |
O1—C5—C6 | 109.1 (2) | O4—C15—C16 | 121.0 (3) |
O1—C5—C4 | 108.2 (2) | O5—C15—C16 | 122.62 (18) |
C6—C5—C4 | 114.3 (2) | C17—C16—C15 | 118.1 (2) |
O1—C5—H5 | 108.4 | C17—C16—C1 | 124.8 (2) |
C6—C5—H5 | 108.4 | C15—C16—C1 | 117.1 (2) |
C4—C5—H5 | 108.4 | C16—C17—H17A | 120.0 |
C5—C6—C7 | 112.7 (3) | C16—C17—H17B | 120.0 |
C5—C6—H6A | 109.0 | H17A—C17—H17B | 120.0 |
C7—C6—H6A | 109.0 | C4—C18—H18A | 109.5 |
C5—C6—H6B | 109.0 | C4—C18—H18B | 109.5 |
C7—C6—H6B | 109.0 | H18A—C18—H18B | 109.5 |
H6A—C6—H6B | 107.8 | C4—C18—H18C | 109.5 |
C8—C7—C6 | 112.5 (3) | H18A—C18—H18C | 109.5 |
C8—C7—H7A | 109.1 | H18B—C18—H18C | 109.5 |
C6—C7—H7A | 109.1 | C8—C19—H19A | 109.5 |
C8—C7—H7B | 109.1 | C8—C19—H19B | 109.5 |
C6—C7—H7B | 109.1 | H19A—C19—H19B | 109.5 |
H7A—C7—H7B | 107.8 | C8—C19—H19C | 109.5 |
C9—C8—C7 | 121.6 (3) | H19A—C19—H19C | 109.5 |
C9—C8—C19 | 121.8 (4) | H19B—C19—H19C | 109.5 |
C7—C8—C19 | 116.6 (3) | C12—C20—H20A | 109.5 |
C8—C9—C10 | 128.2 (3) | C12—C20—H20B | 109.5 |
C8—C9—H9 | 115.9 | H20A—C20—H20B | 109.5 |
C10—C9—H9 | 115.9 | C12—C20—H20C | 109.5 |
C9—C10—C11 | 111.2 (3) | H20A—C20—H20C | 109.5 |
C9—C10—H10A | 109.4 | H20B—C20—H20C | 109.5 |
C11—C10—H10A | 109.4 | H1B—O1W—H2C | 110 |
| | | |
C16—C1—C2—C3 | 37.0 (3) | C10—C11—C12—O2 | −173.7 (2) |
C14—C1—C2—C3 | 163.2 (2) | C10—C11—C12—C20 | −56.5 (3) |
C1—C2—C3—C4 | 48.3 (3) | C10—C11—C12—C13 | 68.8 (3) |
C15—O5—C4—C3 | 2.1 (4) | O2—C12—C13—O3 | 61.2 (2) |
C15—O5—C4—C18 | 121.9 (3) | C20—C12—C13—O3 | −58.5 (3) |
C15—O5—C4—C5 | −121.2 (3) | C11—C12—C13—O3 | 175.70 (18) |
C2—C3—C4—O5 | −68.4 (3) | O2—C12—C13—C14 | −60.3 (3) |
C2—C3—C4—C18 | 176.1 (2) | C20—C12—C13—C14 | 180.0 (2) |
C2—C3—C4—C5 | 50.2 (3) | C11—C12—C13—C14 | 54.2 (2) |
O5—C4—C5—O1 | −172.17 (19) | C16—C1—C14—C13 | −63.2 (2) |
C3—C4—C5—O1 | 64.3 (3) | C2—C1—C14—C13 | 172.63 (19) |
C18—C4—C5—O1 | −61.1 (3) | O3—C13—C14—C1 | 131.89 (18) |
O5—C4—C5—C6 | −50.4 (3) | C12—C13—C14—C1 | −104.5 (2) |
C3—C4—C5—C6 | −173.9 (2) | C4—O5—C15—O4 | −157.9 (3) |
C18—C4—C5—C6 | 60.7 (3) | C4—O5—C15—C16 | 26.2 (4) |
O1—C5—C6—C7 | −100.5 (3) | O4—C15—C16—C17 | 33.4 (4) |
C4—C5—C6—C7 | 138.2 (3) | O5—C15—C16—C17 | −150.8 (3) |
C5—C6—C7—C8 | −67.5 (4) | O4—C15—C16—C1 | −144.7 (3) |
C6—C7—C8—C9 | 106.0 (3) | O5—C15—C16—C1 | 31.0 (3) |
C6—C7—C8—C19 | −71.2 (4) | C14—C1—C16—C17 | −26.2 (3) |
C7—C8—C9—C10 | −171.9 (3) | C2—C1—C16—C17 | 99.2 (3) |
C19—C8—C9—C10 | 5.2 (5) | C14—C1—C16—C15 | 151.80 (19) |
C8—C9—C10—C11 | 156.2 (3) | C2—C1—C16—C15 | −82.8 (2) |
C9—C10—C11—C12 | −151.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.86 | 2.673 (3) | 173 |
O2—H2···O1Wii | 0.82 | 1.95 | 2.755 (4) | 167 |
O3—H3···O4ii | 0.82 | 1.96 | 2.774 (3) | 175 |
O1W—H1B···O1ii | 0.83 | 1.99 | 2.769 (3) | 156 |
O1W—H2C···O3iii | 0.86 | 1.99 | 2.834 (3) | 168 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+2; (ii) −x+1/2, y+1/2, −z+1; (iii) −x+1/2, y−1/2, −z+1. |