The single-crystal structures of calcium D-gluconate and calcium α-D-isosaccharinate have been determined using X-ray diffraction at 100 K. Surprisingly, given its significance in industrial and medical applications, the structure of calcium D-gluconate has not previously been reported. Unexpectedly, the gluconate crystal structure comprises coordination polymers. Unusually, the calcium coordination number is nine. Adjacent metal centres are linked by three μ-oxo bridges, with a metal–metal separation of 3.7312 (2) Å. One of the gluconate ligands contradicts a suggestion from 1974 that a straight chain conformation is associated with an intramolecular hydrogen bond. This ligand binds to three adjacent metal centres. The use of synchrotron radiation provided an improved crystal structure with respect to that previously reported for the isosaccharinate complex, allowing the location of the hydroxy hydrogen sites to be elucidated. In contrast to the gluconate structure, there are no μ-oxo bridges in the isosaccharinate coordination polymer and the isosaccharinate bridging coordination is such that the distance between adjacent metal centres, each of which is eight-coordinate, is 6.7573 (4) Å. Complementing the crystal structure determinations, modelling studies of the geometries and coordination modes for the aqueous [CaGluc]+ and [CaIsa]+ complexes are presented and discussed.
Supporting information
CCDC references: 1846615; 1846616
Data collection: CrysAlis PRO 1.171.39.28e (Rigaku OD, 2015) for (I); mxCuBE v2 (Gabadinho et al. 2010, JSR, 27, 700-707) for (II). Cell refinement: CrysAlis PRO 1.171.39.28e (Rigaku OD, 2015) for (I). Data reduction: CrysAlis PRO 1.171.39.28e (Rigaku OD, 2015) for (I); XDS (Kabsch, 1993) for (II). For both structures, program(s) used to solve structure: ShelxT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2017); molecular graphics: OLEX2 (Dolomanov,O.V. et al., 2009) shelXle (Hübschle,C.B., et al., 2011). Software used to prepare material for publication: WinGX (Farrugia, 1999) for (I); WinGX (Farrugia, 1999) PWT (Farrugia, 2013) PLATON (Spek, A.K., 2003) XNPP (Parsons, S., et al., 2013) ##?? for (II).
Crystal data top
Ca2+·(C6H11O7−)2·H2O | F(000) = 944 |
Mr = 448.39 | Dx = 1.699 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 35610 reflections |
a = 6.71198 (9) Å | θ = 2.1–37.8° |
b = 13.36410 (17) Å | µ = 0.44 mm−1 |
c = 19.5439 (3) Å | T = 100 K |
V = 1753.08 (4) Å3 | Block, colourless |
Z = 4 | 0.11 × 0.03 × 0.02 mm |
Data collection top
AFC12 kappa diffractometer | 9212 independent reflections |
Radiation source: rotating anode | 8854 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.034 |
ω scans | θmax = 38.2°, θmin = 1.9° |
Absorption correction: multi-scan CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −11→11 |
Tmin = 0.898, Tmax = 1.00 | k = −22→23 |
77828 measured reflections | l = −33→33 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.028P)2 + 0.15P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.057 | (Δ/σ)max = 0.001 |
S = 1.19 | Δρmax = 0.42 e Å−3 |
9212 reflections | Δρmin = −0.22 e Å−3 |
301 parameters | Absolute structure: Flack x determined using 3689 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: 0.009 (5) |
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. Oxygen hydrogens sites were located in final difference maps and modelled
with isotropic displacement parameters. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ca1 | 0.26634 (2) | 0.24558 (2) | 0.45839 (2) | 0.00559 (3) | |
O1_1 | −0.00325 (11) | 0.36936 (5) | 0.47873 (4) | 0.00820 (12) | |
O1'_1 | −0.08825 (12) | 0.52935 (6) | 0.49729 (4) | 0.01024 (13) | |
O2_1 | 0.30646 (12) | 0.41108 (5) | 0.40788 (4) | 0.00861 (12) | |
H2O_1 | 0.415 (3) | 0.4297 (16) | 0.3921 (11) | 0.029 (5)* | |
O3_1 | 0.40382 (12) | 0.54686 (6) | 0.51484 (4) | 0.00903 (12) | |
H3O_1 | 0.376 (3) | 0.5829 (16) | 0.5457 (11) | 0.027 (5)* | |
O4_1 | 0.62181 (11) | 0.54189 (6) | 0.39736 (4) | 0.00938 (12) | |
H4O_1 | 0.682 (3) | 0.5440 (16) | 0.4346 (12) | 0.032 (5)* | |
O5_1 | 0.40248 (13) | 0.78659 (6) | 0.42815 (5) | 0.01419 (14) | |
H5O_1 | 0.436 (3) | 0.8358 (15) | 0.4490 (10) | 0.026 (5)* | |
O6_1 | 0.79442 (14) | 0.84239 (6) | 0.38053 (4) | 0.01472 (15) | |
H6O_1 | 0.848 (4) | 0.8592 (17) | 0.3432 (12) | 0.041 (6)* | |
C1_1 | 0.01999 (14) | 0.46160 (7) | 0.47064 (5) | 0.00691 (14) | |
C2_1 | 0.18735 (14) | 0.49597 (7) | 0.42295 (5) | 0.00698 (14) | |
H2_1 | 0.126021 | 0.520187 | 0.379360 | 0.008* | |
C3_1 | 0.30984 (14) | 0.58110 (7) | 0.45351 (5) | 0.00724 (13) | |
H3_1 | 0.219473 | 0.638300 | 0.464702 | 0.009* | |
C4_1 | 0.47065 (14) | 0.61679 (7) | 0.40367 (5) | 0.00775 (14) | |
H4_1 | 0.406700 | 0.624712 | 0.357776 | 0.009* | |
C5_1 | 0.56240 (15) | 0.71782 (7) | 0.42305 (5) | 0.00916 (15) | |
H5_1 | 0.632923 | 0.712413 | 0.467974 | 0.011* | |
C6_1 | 0.70878 (17) | 0.74677 (8) | 0.36712 (6) | 0.01552 (18) | |
H6A_1 | 0.815719 | 0.695909 | 0.364357 | 0.019* | |
H6B_1 | 0.639006 | 0.748384 | 0.322509 | 0.019* | |
O1_2 | −0.38099 (11) | 0.27294 (5) | 0.42671 (4) | 0.00832 (12) | |
O1'_2 | −0.33949 (12) | 0.25678 (7) | 0.31333 (4) | 0.01494 (14) | |
O2_2 | −0.07710 (11) | 0.15128 (5) | 0.45318 (4) | 0.00669 (11) | |
H2O_2 | −0.066 (3) | 0.1024 (16) | 0.4680 (10) | 0.029 (5)* | |
O3_2 | 0.12837 (10) | 0.23842 (5) | 0.34452 (4) | 0.00769 (11) | |
H3O_2 | 0.106 (3) | 0.2818 (14) | 0.3157 (9) | 0.019 (4)* | |
O4_2 | 0.29120 (12) | 0.08544 (6) | 0.39830 (4) | 0.00843 (12) | |
H4O_2 | 0.303 (3) | 0.0406 (16) | 0.4240 (11) | 0.028 (5)* | |
O5_2 | 0.15867 (11) | 0.03141 (6) | 0.22203 (4) | 0.00836 (12) | |
H5O_2 | 0.230 (3) | 0.0319 (14) | 0.1905 (10) | 0.021 (5)* | |
O6_2 | 0.51473 (12) | −0.07791 (6) | 0.22910 (4) | 0.01170 (13) | |
H6O_2 | 0.463 (4) | −0.1333 (18) | 0.2119 (11) | 0.038 (6)* | |
C1_2 | −0.30292 (14) | 0.23433 (7) | 0.37394 (5) | 0.00764 (14) | |
C2_2 | −0.15534 (13) | 0.14770 (7) | 0.38484 (5) | 0.00619 (13) | |
H2_2 | −0.229146 | 0.083236 | 0.379118 | 0.007* | |
C3_2 | 0.01588 (14) | 0.14960 (7) | 0.33347 (5) | 0.00591 (13) | |
H3_2 | −0.038312 | 0.149203 | 0.285810 | 0.007* | |
C4_2 | 0.16006 (14) | 0.06178 (7) | 0.34300 (5) | 0.00630 (13) | |
H4_2 | 0.082714 | 0.000108 | 0.354581 | 0.008* | |
C5_2 | 0.28796 (14) | 0.04182 (7) | 0.27985 (5) | 0.00697 (14) | |
H5_2 | 0.381065 | 0.099188 | 0.272295 | 0.008* | |
C6_2 | 0.40685 (16) | −0.05408 (8) | 0.28983 (5) | 0.01071 (16) | |
H6A_2 | 0.500964 | −0.045562 | 0.328393 | 0.013* | |
H6B_2 | 0.315236 | −0.109682 | 0.301240 | 0.013* | |
O1W | 0.10407 (12) | 0.38372 (6) | 0.25002 (4) | 0.01117 (13) | |
H1WA | 0.221 (4) | 0.4016 (19) | 0.2571 (12) | 0.039 (6)* | |
H1WB | 0.017 (3) | 0.4288 (16) | 0.2667 (10) | 0.027 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.00514 (6) | 0.00573 (6) | 0.00589 (6) | 0.00022 (5) | −0.00026 (5) | −0.00090 (5) |
O1_1 | 0.0083 (3) | 0.0061 (3) | 0.0102 (3) | −0.0009 (2) | 0.0019 (2) | 0.0005 (2) |
O1'_1 | 0.0090 (3) | 0.0080 (3) | 0.0137 (3) | 0.0016 (2) | 0.0034 (2) | −0.0005 (2) |
O2_1 | 0.0081 (3) | 0.0065 (3) | 0.0113 (3) | 0.0002 (2) | 0.0036 (2) | −0.0010 (2) |
O3_1 | 0.0129 (3) | 0.0081 (3) | 0.0061 (3) | 0.0006 (2) | −0.0006 (2) | −0.0002 (2) |
O4_1 | 0.0086 (3) | 0.0104 (3) | 0.0092 (3) | 0.0011 (2) | 0.0017 (2) | −0.0008 (2) |
O5_1 | 0.0133 (3) | 0.0080 (3) | 0.0212 (4) | 0.0004 (3) | 0.0003 (3) | −0.0029 (3) |
O6_1 | 0.0207 (4) | 0.0129 (3) | 0.0105 (3) | −0.0099 (3) | 0.0032 (3) | −0.0017 (2) |
C1_1 | 0.0061 (3) | 0.0071 (3) | 0.0076 (3) | 0.0002 (3) | −0.0001 (3) | 0.0005 (3) |
C2_1 | 0.0067 (3) | 0.0064 (3) | 0.0078 (3) | 0.0002 (3) | 0.0005 (3) | 0.0006 (3) |
C3_1 | 0.0080 (3) | 0.0060 (3) | 0.0077 (3) | −0.0003 (3) | 0.0004 (3) | 0.0005 (3) |
C4_1 | 0.0078 (3) | 0.0071 (3) | 0.0083 (3) | −0.0002 (3) | 0.0009 (3) | 0.0003 (3) |
C5_1 | 0.0099 (4) | 0.0077 (3) | 0.0099 (4) | −0.0023 (3) | 0.0012 (3) | −0.0001 (3) |
C6_1 | 0.0197 (4) | 0.0108 (4) | 0.0161 (4) | −0.0080 (4) | 0.0078 (3) | −0.0031 (3) |
O1_2 | 0.0069 (3) | 0.0092 (3) | 0.0088 (3) | 0.0020 (2) | 0.0013 (2) | −0.0007 (2) |
O1'_2 | 0.0149 (3) | 0.0215 (4) | 0.0084 (3) | 0.0088 (3) | 0.0001 (2) | 0.0037 (3) |
O2_2 | 0.0083 (3) | 0.0069 (3) | 0.0048 (2) | 0.0008 (2) | −0.0004 (2) | 0.0004 (2) |
O3_2 | 0.0090 (3) | 0.0059 (3) | 0.0082 (3) | −0.0014 (2) | −0.0012 (2) | 0.0013 (2) |
O4_2 | 0.0103 (3) | 0.0082 (3) | 0.0067 (3) | 0.0017 (2) | −0.0037 (2) | −0.0011 (2) |
O5_2 | 0.0073 (3) | 0.0131 (3) | 0.0047 (2) | 0.0005 (2) | 0.0002 (2) | −0.0012 (2) |
O6_2 | 0.0099 (3) | 0.0134 (3) | 0.0118 (3) | 0.0016 (3) | 0.0034 (3) | −0.0040 (2) |
C1_2 | 0.0060 (3) | 0.0086 (3) | 0.0084 (3) | 0.0007 (3) | 0.0002 (3) | 0.0004 (3) |
C2_2 | 0.0060 (3) | 0.0073 (3) | 0.0053 (3) | 0.0003 (3) | −0.0002 (3) | −0.0007 (3) |
C3_2 | 0.0062 (3) | 0.0061 (3) | 0.0055 (3) | −0.0001 (3) | 0.0001 (3) | −0.0007 (3) |
C4_2 | 0.0067 (3) | 0.0068 (3) | 0.0054 (3) | 0.0002 (3) | −0.0008 (3) | −0.0012 (3) |
C5_2 | 0.0063 (3) | 0.0085 (3) | 0.0061 (3) | 0.0003 (3) | 0.0001 (3) | −0.0015 (3) |
C6_2 | 0.0110 (4) | 0.0129 (4) | 0.0083 (4) | 0.0054 (3) | 0.0013 (3) | −0.0011 (3) |
O1W | 0.0097 (3) | 0.0126 (3) | 0.0113 (3) | 0.0019 (3) | 0.0005 (3) | 0.0015 (2) |
Geometric parameters (Å, º) top
Ca1—O3_2 | 2.4123 (7) | C4_1—H4_1 | 1.0000 |
Ca1—O2_1 | 2.4370 (8) | C5_1—C6_1 | 1.5198 (14) |
Ca1—O4_2 | 2.4467 (7) | C5_1—H5_1 | 1.0000 |
Ca1—O2_2i | 2.4476 (7) | C6_1—H6A_1 | 0.9900 |
Ca1—O1_2i | 2.4661 (8) | C6_1—H6B_1 | 0.9900 |
Ca1—O1_2ii | 2.4739 (7) | O1_2—C1_2 | 1.2667 (12) |
Ca1—O1_1 | 2.4837 (7) | O1'_2—C1_2 | 1.2464 (12) |
Ca1—O1_1i | 2.5023 (7) | O2_2—C2_2 | 1.4361 (11) |
Ca1—O2_2 | 2.6291 (7) | O2_2—H2O_2 | 0.72 (2) |
Ca1—C3_2 | 3.2298 (9) | O3_2—C3_2 | 1.4232 (11) |
Ca1—Ca1i | 3.7312 (2) | O3_2—H3O_2 | 0.821 (19) |
Ca1—Ca1iii | 3.7312 (1) | O4_2—C4_2 | 1.4294 (12) |
O1_1—C1_1 | 1.2526 (11) | O4_2—H4O_2 | 0.79 (2) |
O1'_1—C1_1 | 1.2724 (12) | O5_2—C5_2 | 1.4316 (12) |
O2_1—C2_1 | 1.4187 (12) | O5_2—H5O_2 | 0.78 (2) |
O2_1—H2O_1 | 0.83 (2) | O6_2—C6_2 | 1.4262 (13) |
O3_1—C3_1 | 1.4297 (12) | O6_2—H6O_2 | 0.88 (2) |
O3_1—H3O_1 | 0.79 (2) | C1_2—C2_2 | 1.5385 (13) |
O4_1—C4_1 | 1.4306 (12) | C2_2—C3_2 | 1.5262 (13) |
O4_1—H4O_1 | 0.83 (2) | C2_2—H2_2 | 1.0000 |
O5_1—C5_1 | 1.4166 (13) | C3_2—C4_2 | 1.5326 (13) |
O5_1—H5O_1 | 0.81 (2) | C3_2—H3_2 | 1.0000 |
O6_1—C6_1 | 1.4255 (13) | C4_2—C5_2 | 1.5269 (13) |
O6_1—H6O_1 | 0.84 (2) | C4_2—H4_2 | 1.0000 |
C1_1—C2_1 | 1.5302 (13) | C5_2—C6_2 | 1.5223 (13) |
C2_1—C3_1 | 1.5255 (13) | C5_2—H5_2 | 1.0000 |
C2_1—H2_1 | 1.0000 | C6_2—H6A_2 | 0.9900 |
C3_1—C4_1 | 1.5301 (13) | C6_2—H6B_2 | 0.9900 |
C3_1—H3_1 | 1.0000 | O1W—H1WA | 0.83 (3) |
C4_1—C5_1 | 1.5315 (13) | O1W—H1WB | 0.90 (2) |
| | | |
O3_2—Ca1—O2_1 | 72.83 (3) | O2_1—C2_1—H2_1 | 108.3 |
O3_2—Ca1—O4_2 | 63.18 (2) | C3_1—C2_1—H2_1 | 108.3 |
O2_1—Ca1—O4_2 | 126.29 (2) | C1_1—C2_1—H2_1 | 108.3 |
O3_2—Ca1—O2_2i | 146.98 (3) | O3_1—C3_1—C2_1 | 109.10 (7) |
O2_1—Ca1—O2_2i | 74.18 (3) | O3_1—C3_1—C4_1 | 108.80 (8) |
O4_2—Ca1—O2_2i | 143.34 (3) | C2_1—C3_1—C4_1 | 111.31 (8) |
O3_2—Ca1—O1_2i | 133.01 (2) | O3_1—C3_1—H3_1 | 109.2 |
O2_1—Ca1—O1_2i | 120.28 (2) | C2_1—C3_1—H3_1 | 109.2 |
O4_2—Ca1—O1_2i | 112.12 (3) | C4_1—C3_1—H3_1 | 109.2 |
O2_2i—Ca1—O1_2i | 65.52 (2) | O4_1—C4_1—C3_1 | 109.70 (7) |
O3_2—Ca1—O1_2ii | 98.18 (2) | O4_1—C4_1—C5_1 | 110.67 (8) |
O2_1—Ca1—O1_2ii | 70.05 (2) | C3_1—C4_1—C5_1 | 113.64 (8) |
O4_2—Ca1—O1_2ii | 86.78 (3) | O4_1—C4_1—H4_1 | 107.5 |
O2_2i—Ca1—O1_2ii | 71.50 (2) | C3_1—C4_1—H4_1 | 107.5 |
O1_2i—Ca1—O1_2ii | 128.78 (2) | C5_1—C4_1—H4_1 | 107.5 |
O3_2—Ca1—O1_1 | 83.94 (2) | O5_1—C5_1—C6_1 | 112.04 (9) |
O2_1—Ca1—O1_1 | 62.67 (2) | O5_1—C5_1—C4_1 | 106.54 (8) |
O4_2—Ca1—O1_1 | 135.16 (3) | C6_1—C5_1—C4_1 | 107.85 (8) |
O2_2i—Ca1—O1_1 | 79.90 (2) | O5_1—C5_1—H5_1 | 110.1 |
O1_2i—Ca1—O1_1 | 68.22 (2) | C6_1—C5_1—H5_1 | 110.1 |
O1_2ii—Ca1—O1_1 | 129.70 (2) | C4_1—C5_1—H5_1 | 110.1 |
O3_2—Ca1—O1_1i | 131.76 (2) | O6_1—C6_1—C5_1 | 110.89 (8) |
O2_1—Ca1—O1_1i | 133.45 (3) | O6_1—C6_1—H6A_1 | 109.5 |
O4_2—Ca1—O1_1i | 69.92 (2) | C5_1—C6_1—H6A_1 | 109.5 |
O2_2i—Ca1—O1_1i | 74.55 (2) | O6_1—C6_1—H6B_1 | 109.5 |
O1_2i—Ca1—O1_1i | 74.88 (2) | C5_1—C6_1—H6B_1 | 109.5 |
O1_2ii—Ca1—O1_1i | 67.80 (2) | H6A_1—C6_1—H6B_1 | 108.0 |
O1_1—Ca1—O1_1i | 141.307 (12) | C1_2—O1_2—Ca1iii | 122.32 (6) |
O3_2—Ca1—O2_2 | 66.97 (2) | C1_2—O1_2—Ca1iv | 122.64 (6) |
O2_1—Ca1—O2_2 | 121.08 (2) | Ca1iii—O1_2—Ca1iv | 98.10 (3) |
O4_2—Ca1—O2_2 | 67.79 (2) | C2_2—O2_2—Ca1iii | 121.23 (5) |
O2_2i—Ca1—O2_2 | 132.35 (2) | C2_2—O2_2—Ca1 | 111.88 (5) |
O1_2i—Ca1—O2_2 | 68.63 (2) | Ca1iii—O2_2—Ca1 | 94.54 (2) |
O1_2ii—Ca1—O2_2 | 154.17 (2) | C2_2—O2_2—H2O_2 | 112.4 (17) |
O1_1—Ca1—O2_2 | 71.74 (2) | Ca1iii—O2_2—H2O_2 | 105.8 (16) |
O1_1i—Ca1—O2_2 | 105.47 (2) | Ca1—O2_2—H2O_2 | 109.4 (18) |
O3_2—Ca1—C3_2 | 24.09 (2) | C3_2—O3_2—Ca1 | 112.13 (5) |
O2_1—Ca1—C3_2 | 96.42 (2) | C3_2—O3_2—H3O_2 | 112.9 (13) |
O4_2—Ca1—C3_2 | 47.58 (2) | Ca1—O3_2—H3O_2 | 132.3 (13) |
O2_2i—Ca1—C3_2 | 168.76 (2) | C4_2—O4_2—Ca1 | 120.96 (6) |
O1_2i—Ca1—C3_2 | 116.09 (2) | C4_2—O4_2—H4O_2 | 112.2 (16) |
O1_2ii—Ca1—C3_2 | 111.57 (2) | Ca1—O4_2—H4O_2 | 111.6 (15) |
O1_1—Ca1—C3_2 | 90.36 (2) | C5_2—O5_2—H5O_2 | 104.4 (14) |
O1_1i—Ca1—C3_2 | 116.69 (2) | C6_2—O6_2—H6O_2 | 107.7 (15) |
O2_2—Ca1—C3_2 | 47.47 (2) | O1'_2—C1_2—O1_2 | 126.46 (9) |
O3_2—Ca1—Ca1i | 138.476 (18) | O1'_2—C1_2—C2_2 | 116.08 (8) |
O2_1—Ca1—Ca1i | 92.78 (2) | O1_2—C1_2—C2_2 | 117.39 (8) |
O4_2—Ca1—Ca1i | 100.113 (19) | O2_2—C2_2—C3_2 | 109.63 (7) |
O2_2i—Ca1—Ca1i | 44.620 (17) | O2_2—C2_2—C1_2 | 109.83 (7) |
O1_2i—Ca1—Ca1i | 88.103 (18) | C3_2—C2_2—C1_2 | 112.40 (7) |
O1_2ii—Ca1—Ca1i | 40.869 (17) | O2_2—C2_2—H2_2 | 108.3 |
O1_1—Ca1—Ca1i | 124.358 (19) | C3_2—C2_2—H2_2 | 108.3 |
O1_1i—Ca1—Ca1i | 41.365 (17) | C1_2—C2_2—H2_2 | 108.3 |
O2_2—Ca1—Ca1i | 145.151 (18) | O3_2—C3_2—C2_2 | 108.28 (7) |
C3_2—Ca1—Ca1i | 144.120 (17) | O3_2—C3_2—C4_2 | 106.58 (7) |
O3_2—Ca1—Ca1iii | 93.332 (18) | C2_2—C3_2—C4_2 | 112.51 (7) |
O2_1—Ca1—Ca1iii | 104.311 (19) | O3_2—C3_2—Ca1 | 43.78 (4) |
O4_2—Ca1—Ca1iii | 107.35 (2) | C2_2—C3_2—Ca1 | 84.34 (5) |
O2_2i—Ca1—Ca1iii | 93.469 (18) | C4_2—C3_2—Ca1 | 83.32 (5) |
O1_2i—Ca1—Ca1iii | 41.026 (17) | O3_2—C3_2—H3_2 | 109.8 |
O1_2ii—Ca1—Ca1iii | 164.798 (19) | C2_2—C3_2—H3_2 | 109.8 |
O1_1—Ca1—Ca1iii | 41.741 (17) | C4_2—C3_2—H3_2 | 109.8 |
O1_1i—Ca1—Ca1iii | 111.179 (19) | Ca1—C3_2—H3_2 | 153.6 |
O2_2—Ca1—Ca1iii | 40.838 (15) | O4_2—C4_2—C5_2 | 107.68 (7) |
C3_2—Ca1—Ca1iii | 82.757 (16) | O4_2—C4_2—C3_2 | 108.14 (7) |
Ca1i—Ca1—Ca1iii | 128.166 (9) | C5_2—C4_2—C3_2 | 112.99 (7) |
C1_1—O1_1—Ca1 | 122.99 (6) | O4_2—C4_2—H4_2 | 109.3 |
C1_1—O1_1—Ca1iii | 138.00 (6) | C5_2—C4_2—H4_2 | 109.3 |
Ca1—O1_1—Ca1iii | 96.90 (2) | C3_2—C4_2—H4_2 | 109.3 |
C2_1—O2_1—Ca1 | 125.41 (6) | O5_2—C5_2—C6_2 | 109.70 (7) |
C2_1—O2_1—H2O_1 | 109.5 (15) | O5_2—C5_2—C4_2 | 108.31 (7) |
Ca1—O2_1—H2O_1 | 121.2 (15) | C6_2—C5_2—C4_2 | 109.77 (8) |
C3_1—O3_1—H3O_1 | 109.8 (15) | O5_2—C5_2—H5_2 | 109.7 |
C4_1—O4_1—H4O_1 | 104.3 (15) | C6_2—C5_2—H5_2 | 109.7 |
C5_1—O5_1—H5O_1 | 110.9 (15) | C4_2—C5_2—H5_2 | 109.7 |
C6_1—O6_1—H6O_1 | 104.6 (16) | O6_2—C6_2—C5_2 | 110.34 (8) |
O1_1—C1_1—O1'_1 | 125.28 (9) | O6_2—C6_2—H6A_2 | 109.6 |
O1_1—C1_1—C2_1 | 117.63 (8) | C5_2—C6_2—H6A_2 | 109.6 |
O1'_1—C1_1—C2_1 | 117.06 (8) | O6_2—C6_2—H6B_2 | 109.6 |
O2_1—C2_1—C3_1 | 111.96 (8) | C5_2—C6_2—H6B_2 | 109.6 |
O2_1—C2_1—C1_1 | 107.46 (7) | H6A_2—C6_2—H6B_2 | 108.1 |
C3_1—C2_1—C1_1 | 112.40 (7) | H1WA—O1W—H1WB | 111 (2) |
| | | |
Ca1—O1_1—C1_1—O1'_1 | −159.42 (7) | Ca1—O2_2—C2_2—C3_2 | 28.53 (8) |
Ca1iii—O1_1—C1_1—O1'_1 | −0.22 (16) | Ca1iii—O2_2—C2_2—C1_2 | 14.63 (9) |
Ca1—O1_1—C1_1—C2_1 | 22.82 (11) | Ca1—O2_2—C2_2—C1_2 | −95.44 (7) |
Ca1iii—O1_1—C1_1—C2_1 | −177.97 (6) | O1'_2—C1_2—C2_2—O2_2 | 161.00 (9) |
Ca1—O2_1—C2_1—C3_1 | 118.55 (7) | O1_2—C1_2—C2_2—O2_2 | −21.77 (11) |
Ca1—O2_1—C2_1—C1_1 | −5.34 (10) | O1'_2—C1_2—C2_2—C3_2 | 38.66 (12) |
O1_1—C1_1—C2_1—O2_1 | −10.97 (11) | O1_2—C1_2—C2_2—C3_2 | −144.10 (8) |
O1'_1—C1_1—C2_1—O2_1 | 171.09 (8) | Ca1—O3_2—C3_2—C2_2 | 60.34 (8) |
O1_1—C1_1—C2_1—C3_1 | −134.59 (9) | Ca1—O3_2—C3_2—C4_2 | −60.92 (7) |
O1'_1—C1_1—C2_1—C3_1 | 47.47 (11) | O2_2—C2_2—C3_2—O3_2 | −58.43 (9) |
O2_1—C2_1—C3_1—O3_1 | −58.88 (10) | C1_2—C2_2—C3_2—O3_2 | 64.02 (9) |
C1_1—C2_1—C3_1—O3_1 | 62.19 (10) | O2_2—C2_2—C3_2—C4_2 | 59.09 (10) |
O2_1—C2_1—C3_1—C4_1 | 61.19 (10) | C1_2—C2_2—C3_2—C4_2 | −178.46 (7) |
C1_1—C2_1—C3_1—C4_1 | −177.73 (7) | O2_2—C2_2—C3_2—Ca1 | −21.26 (6) |
O3_1—C3_1—C4_1—O4_1 | 49.97 (10) | C1_2—C2_2—C3_2—Ca1 | 101.19 (7) |
C2_1—C3_1—C4_1—O4_1 | −70.28 (10) | Ca1—O4_2—C4_2—C5_2 | 121.17 (7) |
O3_1—C3_1—C4_1—C5_1 | −74.50 (10) | Ca1—O4_2—C4_2—C3_2 | −1.23 (9) |
C2_1—C3_1—C4_1—C5_1 | 165.25 (8) | O3_2—C3_2—C4_2—O4_2 | 38.30 (9) |
O4_1—C4_1—C5_1—O5_1 | −179.94 (8) | C2_2—C3_2—C4_2—O4_2 | −80.22 (9) |
C3_1—C4_1—C5_1—O5_1 | −55.99 (10) | Ca1—C3_2—C4_2—O4_2 | 0.80 (6) |
O4_1—C4_1—C5_1—C6_1 | 59.61 (10) | O3_2—C3_2—C4_2—C5_2 | −80.78 (9) |
C3_1—C4_1—C5_1—C6_1 | −176.44 (8) | C2_2—C3_2—C4_2—C5_2 | 160.70 (7) |
O5_1—C5_1—C6_1—O6_1 | 60.77 (12) | Ca1—C3_2—C4_2—C5_2 | −118.28 (7) |
C4_1—C5_1—C6_1—O6_1 | 177.71 (9) | O4_2—C4_2—C5_2—O5_2 | −172.27 (7) |
Ca1iii—O1_2—C1_2—O1'_2 | −163.24 (8) | C3_2—C4_2—C5_2—O5_2 | −52.92 (10) |
Ca1iv—O1_2—C1_2—O1'_2 | 69.65 (12) | O4_2—C4_2—C5_2—C6_2 | 67.99 (9) |
Ca1iii—O1_2—C1_2—C2_2 | 19.84 (11) | C3_2—C4_2—C5_2—C6_2 | −172.67 (8) |
Ca1iv—O1_2—C1_2—C2_2 | −107.27 (8) | O5_2—C5_2—C6_2—O6_2 | 56.45 (10) |
Ca1iii—O2_2—C2_2—C3_2 | 138.60 (6) | C4_2—C5_2—C6_2—O6_2 | 175.35 (8) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2_1—H2O_1···O4_1 | 0.83 (2) | 2.04 (2) | 2.7529 (11) | 143 (2) |
O2_1—H2O_1···O6_2v | 0.83 (2) | 2.42 (2) | 2.9376 (11) | 121.4 (18) |
O3_1—H3O_1···O6_1vi | 0.79 (2) | 1.84 (2) | 2.6290 (11) | 175 (2) |
O4_1—H4O_1···O1′_1ii | 0.83 (2) | 1.98 (2) | 2.7621 (11) | 156 (2) |
O5_1—H5O_1···O1′_1vii | 0.81 (2) | 2.09 (2) | 2.8597 (11) | 160 (2) |
O6_1—H6O_1···O1Wv | 0.84 (2) | 1.88 (2) | 2.6980 (12) | 163 (2) |
O2_2—H2O_2···O2_1iii | 0.72 (2) | 2.58 (2) | 2.9459 (10) | 114.1 (19) |
O2_2—H2O_2···O3_1iii | 0.72 (2) | 2.03 (2) | 2.7237 (10) | 162 (2) |
O3_2—H3O_2···O1W | 0.821 (19) | 1.872 (19) | 2.6849 (10) | 170.0 (19) |
O4_2—H4O_2···O1′_1i | 0.79 (2) | 1.94 (2) | 2.6781 (11) | 156 (2) |
O5_2—H5O_2···O4_1viii | 0.78 (2) | 1.99 (2) | 2.7631 (10) | 171 (2) |
O6_2—H6O_2···O1′_2ix | 0.88 (2) | 1.76 (2) | 2.6367 (12) | 173 (2) |
O1W—H1WA···O6_2v | 0.83 (3) | 1.81 (3) | 2.6412 (11) | 172 (2) |
O1W—H1WB···O5_2x | 0.90 (2) | 1.82 (2) | 2.7026 (11) | 165.4 (19) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, −z+1; (v) −x+1, y+1/2, −z+1/2; (vi) x−1/2, −y+3/2, −z+1; (vii) x+1/2, −y+3/2, −z+1; (viii) −x+1, y−1/2, −z+1/2; (ix) −x, y−1/2, −z+1/2; (x) −x, y+1/2, −z+1/2. |
Crystal data top
Ca2+·(C6H11O6−)2 | F(000) = 420 |
Mr = 398.37 | Dx = 1.743 Mg m−3 |
Orthorhombic, P21212 | Synchrotron radiation, λ = 0.7749 Å |
Hall symbol: P 2 2ab | Cell parameters from 3861 reflections |
a = 6.7573 (4) Å | θ = 2.3–28.5° |
b = 19.5874 (10) Å | µ = 0.60 mm−1 |
c = 5.7344 (10) Å | T = 100 K |
V = 758.99 (14) Å3 | Needle, colourless |
Z = 2 | 0.10 × 0.01 × 0.01 mm |
Data collection top
Pilatus 6M-F (25 Hz) and MD2 mini-kappa diffractometer | 1393 reflections with I > 2σ(I) |
Radiation source: EMBL PETRA III P13-MX1 beamline | Rint = 0.069 |
Silicon Double Crystal monochromator | θmax = 28.5°, θmin = 2.3° |
Phi Scan scans | h = −8→8 |
4539 measured reflections | k = −23→22 |
1394 independent reflections | l = −6→6 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.03P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.033 | (Δ/σ)max < 0.001 |
wR(F2) = 0.082 | Δρmax = 0.29 e Å−3 |
S = 1.07 | Δρmin = −0.60 e Å−3 |
1394 reflections | Extinction correction: SHELXL-2017/1 (Sheldrick 2017), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
131 parameters | Extinction coefficient: 0.180 (14) |
2 restraints | Absolute structure: Flack x determined using 541 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Hydrogen site location: mixed | Absolute structure parameter: 0.050 (19) |
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. The non-hydrogen atoms in the asymmetric unit were modelled with
anisotropic displacement parameters and in general a riding atom
model was used for the hydrogen atoms in the model. The hydroxyl
hydrogen sites were located in final difference maps and their
positions were refined together with isotropic displacement parameters.
A distance restraint was used for H5O and H6O. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ca1 | 0.000000 | 0.000000 | 0.27017 (12) | 0.0076 (3) | |
O1 | 0.8314 (3) | 0.05988 (9) | −0.0319 (3) | 0.0120 (5) | |
O1' | 0.7387 (3) | 0.15945 (8) | −0.1862 (4) | 0.0119 (5) | |
O2 | 0.8417 (3) | 0.10593 (8) | 0.3908 (4) | 0.0095 (5) | |
H2O | 0.814 (6) | 0.119 (2) | 0.524 (8) | 0.019 (10)* | |
O4 | 0.2489 (3) | 0.08962 (9) | 0.1599 (4) | 0.0121 (5) | |
H4O | 0.190 (7) | 0.130 (3) | 0.171 (9) | 0.036 (12)* | |
O5 | 0.2223 (3) | 0.02716 (10) | 0.5792 (4) | 0.0148 (5) | |
H5O | 0.208 (7) | 0.013 (2) | 0.716 (5) | 0.036 (12)* | |
O6 | 1.0579 (3) | 0.21470 (9) | 0.1967 (4) | 0.0144 (5) | |
H6O | 1.110 (7) | 0.2533 (15) | 0.195 (10) | 0.046 (14)* | |
C1 | 0.7776 (3) | 0.12109 (13) | −0.0161 (5) | 0.0092 (6) | |
C2 | 0.7524 (4) | 0.15195 (12) | 0.2298 (5) | 0.0087 (6) | |
C3 | 0.5309 (4) | 0.16147 (12) | 0.2837 (5) | 0.0108 (6) | |
H3A | 0.518113 | 0.189337 | 0.426976 | 0.013* | |
H3B | 0.469600 | 0.187438 | 0.154444 | 0.013* | |
C4 | 0.4146 (4) | 0.09469 (13) | 0.3179 (5) | 0.0124 (6) | |
H4 | 0.506161 | 0.055787 | 0.284519 | 0.015* | |
C5 | 0.3417 (5) | 0.08721 (14) | 0.5673 (6) | 0.0168 (7) | |
H5A | 0.455487 | 0.083210 | 0.675242 | 0.020* | |
H5B | 0.263008 | 0.127719 | 0.612701 | 0.020* | |
C6 | 0.8531 (4) | 0.22175 (12) | 0.2493 (6) | 0.0108 (6) | |
H6A | 0.790987 | 0.254243 | 0.139162 | 0.013* | |
H6B | 0.836824 | 0.239892 | 0.409293 | 0.013* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.0093 (4) | 0.0043 (4) | 0.0092 (4) | 0.0004 (2) | 0.000 | 0.000 |
O1 | 0.0197 (9) | 0.0067 (9) | 0.0096 (11) | 0.0030 (7) | −0.0017 (8) | −0.0019 (7) |
O1' | 0.0191 (9) | 0.0085 (9) | 0.0081 (12) | 0.0036 (7) | −0.0011 (8) | −0.0001 (7) |
O2 | 0.0142 (9) | 0.0068 (9) | 0.0075 (12) | 0.0032 (7) | −0.0005 (8) | 0.0005 (7) |
O4 | 0.0134 (9) | 0.0081 (9) | 0.0150 (13) | −0.0014 (7) | −0.0008 (7) | 0.0003 (7) |
O5 | 0.0199 (10) | 0.0116 (9) | 0.0129 (12) | −0.0079 (7) | −0.0035 (8) | 0.0052 (8) |
O6 | 0.0113 (9) | 0.0073 (8) | 0.0245 (13) | −0.0031 (7) | 0.0021 (8) | 0.0012 (8) |
C1 | 0.0089 (11) | 0.0074 (12) | 0.0113 (16) | −0.0006 (9) | −0.0004 (10) | −0.0003 (10) |
C2 | 0.0112 (11) | 0.0052 (11) | 0.0098 (16) | 0.0006 (8) | −0.0003 (11) | −0.0002 (10) |
C3 | 0.0108 (11) | 0.0074 (11) | 0.0142 (15) | 0.0011 (8) | 0.0013 (11) | −0.0008 (9) |
C4 | 0.0112 (11) | 0.0079 (10) | 0.0179 (18) | −0.0006 (9) | −0.0009 (11) | 0.0005 (11) |
C5 | 0.0191 (13) | 0.0131 (13) | 0.0181 (19) | −0.0072 (10) | −0.0011 (12) | 0.0005 (11) |
C6 | 0.0122 (12) | 0.0065 (11) | 0.0138 (16) | −0.0004 (8) | −0.0025 (12) | −0.0018 (9) |
Geometric parameters (Å, º) top
Ca1—O1i | 2.382 (2) | O5—H5O | 0.84 (2) |
Ca1—O1ii | 2.382 (2) | O6—C6 | 1.423 (3) |
Ca1—O5iii | 2.383 (2) | O6—H6O | 0.83 (2) |
Ca1—O5 | 2.383 (2) | C1—C2 | 1.543 (4) |
Ca1—O2ii | 2.4347 (17) | C2—C6 | 1.531 (3) |
Ca1—O2i | 2.4347 (17) | C2—C3 | 1.540 (3) |
Ca1—O4iii | 2.5119 (18) | C3—C4 | 1.539 (3) |
Ca1—O4 | 2.5120 (18) | C3—H3A | 0.9900 |
O1—C1 | 1.256 (3) | C3—H3B | 0.9900 |
O1'—C1 | 1.259 (4) | C4—C5 | 1.520 (4) |
O2—C2 | 1.425 (3) | C4—H4 | 1.0000 |
O2—H2O | 0.83 (4) | C5—H5A | 0.9900 |
O4—C4 | 1.444 (3) | C5—H5B | 0.9900 |
O4—H4O | 0.88 (5) | C6—H6A | 0.9900 |
O5—C5 | 1.428 (3) | C6—H6B | 0.9900 |
| | | |
O1i—Ca1—O1ii | 86.70 (10) | C5—O5—H5O | 113 (3) |
O1i—Ca1—O5iii | 137.08 (6) | Ca1—O5—H5O | 123 (3) |
O1ii—Ca1—O5iii | 110.44 (7) | C6—O6—H6O | 109 (3) |
O1i—Ca1—O5 | 110.44 (7) | O1—C1—O1' | 125.1 (3) |
O1ii—Ca1—O5 | 137.08 (6) | O1—C1—C2 | 118.1 (2) |
O5iii—Ca1—O5 | 83.92 (11) | O1'—C1—C2 | 116.8 (2) |
O1i—Ca1—O2ii | 146.76 (7) | O2—C2—C6 | 109.2 (2) |
O1ii—Ca1—O2ii | 64.97 (7) | O2—C2—C3 | 111.0 (2) |
O5iii—Ca1—O2ii | 72.66 (7) | C6—C2—C3 | 108.00 (19) |
O5—Ca1—O2ii | 82.84 (7) | O2—C2—C1 | 107.32 (19) |
O1i—Ca1—O2i | 64.97 (7) | C6—C2—C1 | 111.6 (2) |
O1ii—Ca1—O2i | 146.76 (7) | C3—C2—C1 | 109.8 (2) |
O5iii—Ca1—O2i | 82.84 (7) | C4—C3—C2 | 114.79 (19) |
O5—Ca1—O2i | 72.66 (7) | C4—C3—H3A | 108.6 |
O2ii—Ca1—O2i | 146.98 (10) | C2—C3—H3A | 108.6 |
O1i—Ca1—O4iii | 78.06 (7) | C4—C3—H3B | 108.6 |
O1ii—Ca1—O4iii | 80.84 (7) | C2—C3—H3B | 108.6 |
O5iii—Ca1—O4iii | 67.00 (7) | H3A—C3—H3B | 107.5 |
O5—Ca1—O4iii | 139.92 (7) | O4—C4—C5 | 109.4 (2) |
O2ii—Ca1—O4iii | 111.90 (6) | O4—C4—C3 | 112.0 (2) |
O2i—Ca1—O4iii | 76.71 (6) | C5—C4—C3 | 111.6 (2) |
O1i—Ca1—O4 | 80.84 (7) | O4—C4—H4 | 107.9 |
O1ii—Ca1—O4 | 78.06 (7) | C5—C4—H4 | 107.9 |
O5iii—Ca1—O4 | 139.92 (7) | C3—C4—H4 | 107.9 |
O5—Ca1—O4 | 67.00 (7) | O5—C5—C4 | 107.9 (2) |
O2ii—Ca1—O4 | 76.71 (6) | O5—C5—H5A | 110.1 |
O2i—Ca1—O4 | 111.90 (6) | C4—C5—H5A | 110.1 |
O4iii—Ca1—O4 | 150.84 (11) | O5—C5—H5B | 110.1 |
C1—O1—Ca1iv | 123.79 (17) | C4—C5—H5B | 110.1 |
C2—O2—Ca1iv | 122.76 (17) | H5A—C5—H5B | 108.4 |
C2—O2—H2O | 108 (3) | O6—C6—C2 | 109.3 (2) |
Ca1iv—O2—H2O | 129 (3) | O6—C6—H6A | 109.8 |
C4—O4—Ca1 | 114.16 (15) | C2—C6—H6A | 109.8 |
C4—O4—H4O | 104 (3) | O6—C6—H6B | 109.8 |
Ca1—O4—H4O | 107 (3) | C2—C6—H6B | 109.8 |
C5—O5—Ca1 | 120.31 (17) | H6A—C6—H6B | 108.3 |
| | | |
Ca1iv—O1—C1—O1' | 159.60 (19) | C6—C2—C3—C4 | −168.9 (2) |
Ca1iv—O1—C1—C2 | −21.7 (3) | C1—C2—C3—C4 | 69.3 (3) |
Ca1iv—O2—C2—C6 | −120.95 (19) | Ca1—O4—C4—C5 | −40.2 (2) |
Ca1iv—O2—C2—C3 | 120.09 (19) | Ca1—O4—C4—C3 | −164.43 (15) |
Ca1iv—O2—C2—C1 | 0.2 (2) | C2—C3—C4—O4 | −123.3 (3) |
O1—C1—C2—O2 | 13.0 (3) | C2—C3—C4—C5 | 113.6 (3) |
O1'—C1—C2—O2 | −168.20 (19) | Ca1—O5—C5—C4 | −40.0 (3) |
O1—C1—C2—C6 | 132.7 (2) | O4—C4—C5—O5 | 50.8 (3) |
O1'—C1—C2—C6 | −48.6 (3) | C3—C4—C5—O5 | 175.3 (2) |
O1—C1—C2—C3 | −107.7 (2) | O2—C2—C6—O6 | 60.1 (3) |
O1'—C1—C2—C3 | 71.1 (3) | C3—C2—C6—O6 | −179.1 (2) |
O2—C2—C3—C4 | −49.2 (3) | C1—C2—C6—O6 | −58.4 (3) |
Symmetry codes: (i) −x+1, −y, z; (ii) x−1, y, z; (iii) −x, −y, z; (iv) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6O···O1′v | 0.83 (2) | 1.92 (3) | 2.752 (2) | 178 (5) |
O2—H2O···O1′vi | 0.83 (4) | 1.91 (5) | 2.733 (3) | 173 (4) |
O4—H4O···O6ii | 0.88 (5) | 1.90 (5) | 2.777 (3) | 179 (5) |
O5—H5O···O1vii | 0.84 (2) | 2.05 (3) | 2.831 (3) | 155 (4) |
C5—H5A···O1′vi | 0.99 | 2.55 | 3.346 (4) | 137 |
C6—H6A···O6viii | 0.99 | 2.56 | 3.474 (3) | 153 |
Symmetry codes: (ii) x−1, y, z; (v) x+1/2, −y+1/2, −z; (vi) x, y, z+1; (vii) −x+1, −y, z+1; (viii) x−1/2, −y+1/2, −z. |