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In the crystal structure of the title compound, C14H26NO8+·Cl-·2H2O, both the cation and anion lie on special positions of site symmetry 2. The cation and anion, along with the water molecules of crystallization, are linked into a three-dimensional network by extensive hydrogen bonds.
Supporting information
CCDC reference: 289896
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.093
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 2
Calculated cell volume su = 9.36
Cell volume su given = 7.00
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.52 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
PLAT736_ALERT_1_C H...A Calc 2.69(3), Rep 2.690(10) ...... 3.00 su-Rat
H1N -CL1 1.555 4.555
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 27.02
From the CIF: _reflns_number_total 2006
Count of symmetry unique reflns 1260
Completeness (_total/calc) 159.21%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 746
Fraction of Friedel pairs measured 0.592
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(+)-(
Z)-(1
S,2S,3
S,4
R,1'
S,2'
S,3'
S,4'
R,5'
R)-2,3,4-Trihydroxy-5-(hydroxymethyl)-
N-[2',3',4'-trihydroxy-5'-(hydroxymethyl)cyclohex-1'-yl]cyclohex-5-en-1-aminium chloride dihydrate
top
Crystal data top
C14H26NO8+·Cl−·2H2O | Dx = 1.479 Mg m−3 |
Mr = 407.84 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 7629 reflections |
Hall symbol: P 4nw 2abw | θ = 2.6–27.0° |
a = 7.9421 (3) Å | µ = 0.26 mm−1 |
c = 29.028 (1) Å | T = 295 K |
V = 1831.00 (7) Å3 | Block, colorless |
Z = 4 | 0.47 × 0.38 × 0.34 mm |
F(000) = 872 | |
Data collection top
Bruker AXS SMART 1000 CCD diffractometer | 2006 independent reflections |
Radiation source: fine-focus sealed tube | 1894 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 27.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.887, Tmax = 0.916 | k = −9→10 |
10894 measured reflections | l = −32→37 |
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.044P)2 + 0.4597P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
2006 reflections | Δρmax = 0.18 e Å−3 |
157 parameters | Δρmin = −0.28 e Å−3 |
12 restraints | Absolute structure: Flack (1983), 746 Friedel pairs' |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.16 (9) |
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) |
Cl1 | 0.78520 (6) | 0.21480 (6) | 0.2500 | 0.03180 (17) | |
O1 | 0.8202 (2) | 0.12795 (19) | 0.57110 (4) | 0.0340 (3) | |
O2 | 0.5027 (2) | 0.2373 (2) | 0.53977 (5) | 0.0381 (4) | |
O3 | 0.44967 (18) | 0.2363 (2) | 0.44334 (5) | 0.0335 (3) | |
O4 | 0.8688 (2) | 0.2610 (2) | 0.35485 (4) | 0.0427 (4) | |
O1W | 0.9804 (2) | 0.3727 (2) | 0.61949 (5) | 0.0369 (4) | |
N1 | 0.9918 (2) | −0.0082 (2) | 0.5000 | 0.0318 (5) | |
C1 | 0.9488 (2) | 0.1762 (2) | 0.49673 (7) | 0.0283 (4) | |
H1 | 1.0477 | 0.2447 | 0.5043 | 0.034* | |
C2 | 0.8031 (2) | 0.2195 (2) | 0.52910 (6) | 0.0271 (4) | |
H2 | 0.8086 | 0.3400 | 0.5362 | 0.032* | |
C3 | 0.6305 (2) | 0.1815 (2) | 0.50903 (6) | 0.0245 (4) | |
H3 | 0.6192 | 0.0601 | 0.5039 | 0.029* | |
C4 | 0.6098 (2) | 0.2745 (2) | 0.46354 (6) | 0.0245 (4) | |
H4 | 0.6103 | 0.3953 | 0.4705 | 0.029* | |
C5 | 0.752 (3) | 0.242 (3) | 0.4295 (7) | 0.024 (2) | 0.50 |
C6 | 0.9090 (7) | 0.1894 (6) | 0.44445 (15) | 0.0262 (8) | 0.50 |
H6 | 0.9913 | 0.1615 | 0.4230 | 0.031* | 0.50 |
C7 | 0.717 (4) | 0.276 (3) | 0.3789 (8) | 0.030 (2) | 0.50 |
H7A | 0.6354 | 0.1959 | 0.3673 | 0.036* | 0.50 |
H7B | 0.6713 | 0.3887 | 0.3751 | 0.036* | 0.50 |
C5' | 0.750 (2) | 0.212 (3) | 0.4319 (7) | 0.024 (2) | 0.50 |
H5' | 0.7438 | 0.0893 | 0.4287 | 0.029* | 0.50 |
C6' | 0.9147 (7) | 0.2621 (6) | 0.45112 (15) | 0.0262 (8) | 0.50 |
H6'1 | 0.9167 | 0.3832 | 0.4554 | 0.031* | 0.50 |
H6'2 | 1.0029 | 0.2330 | 0.4294 | 0.031* | 0.50 |
C7' | 0.726 (4) | 0.296 (3) | 0.3852 (8) | 0.030 (2) | 0.50 |
H7'1 | 0.6235 | 0.2543 | 0.3710 | 0.036* | 0.50 |
H7'2 | 0.7148 | 0.4164 | 0.3893 | 0.036* | 0.50 |
H1O | 0.865 (3) | 0.197 (3) | 0.5894 (7) | 0.046 (8)* | |
H2O | 0.518 (4) | 0.198 (3) | 0.5667 (5) | 0.053 (8)* | |
H3O | 0.380 (3) | 0.312 (3) | 0.4498 (9) | 0.057 (9)* | |
H4O | 0.848 (4) | 0.243 (4) | 0.3266 (5) | 0.075 (10)* | |
H1W1 | 1.069 (2) | 0.385 (3) | 0.6033 (8) | 0.053 (8)* | |
H1W2 | 0.916 (3) | 0.458 (3) | 0.6156 (11) | 0.081 (12)* | |
H1N | 0.942 (4) | −0.049 (4) | 0.5238 (2) | 0.102 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0332 (2) | 0.0332 (2) | 0.0290 (3) | 0.0090 (3) | −0.00186 (19) | −0.00186 (19) |
O1 | 0.0480 (9) | 0.0336 (8) | 0.0204 (6) | 0.0008 (6) | −0.0082 (6) | 0.0042 (6) |
O2 | 0.0415 (8) | 0.0456 (9) | 0.0272 (6) | 0.0190 (8) | 0.0075 (6) | 0.0071 (6) |
O3 | 0.0294 (7) | 0.0385 (9) | 0.0327 (7) | 0.0095 (6) | −0.0095 (6) | −0.0088 (6) |
O4 | 0.0418 (9) | 0.0654 (11) | 0.0208 (7) | −0.0070 (8) | 0.0004 (6) | 0.0008 (7) |
O1W | 0.0392 (9) | 0.0428 (9) | 0.0287 (7) | −0.0043 (7) | −0.0003 (6) | 0.0005 (6) |
N1 | 0.0278 (7) | 0.0278 (7) | 0.0398 (12) | −0.0075 (9) | 0.0071 (8) | −0.0071 (8) |
C1 | 0.0264 (9) | 0.0285 (10) | 0.0299 (9) | −0.0061 (7) | −0.0072 (8) | 0.0113 (8) |
C2 | 0.0387 (10) | 0.0212 (8) | 0.0213 (7) | 0.0008 (8) | −0.0084 (7) | 0.0015 (7) |
C3 | 0.0299 (9) | 0.0213 (9) | 0.0223 (8) | 0.0053 (7) | −0.0003 (7) | −0.0004 (6) |
C4 | 0.0280 (9) | 0.0234 (9) | 0.0223 (8) | 0.0044 (7) | −0.0055 (7) | −0.0022 (7) |
C5 | 0.0319 (11) | 0.019 (7) | 0.0216 (17) | 0.005 (3) | −0.0018 (9) | 0.003 (3) |
C6 | 0.0287 (11) | 0.027 (2) | 0.0228 (14) | 0.000 (2) | 0.0008 (11) | 0.0087 (18) |
C7 | 0.034 (3) | 0.041 (4) | 0.016 (5) | −0.003 (3) | −0.005 (3) | 0.002 (3) |
C5' | 0.0319 (11) | 0.019 (7) | 0.0216 (17) | 0.005 (3) | −0.0018 (9) | 0.003 (3) |
C6' | 0.0287 (11) | 0.027 (2) | 0.0228 (14) | 0.000 (2) | 0.0008 (11) | 0.0087 (18) |
C7' | 0.034 (3) | 0.041 (4) | 0.016 (5) | −0.003 (3) | −0.005 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
O1—C2 | 1.426 (2) | C2—H2 | 0.9800 |
O1—H1O | 0.839 (10) | C3—C4 | 1.522 (2) |
O2—C3 | 1.422 (2) | C3—H3 | 0.9800 |
O2—H2O | 0.849 (10) | C4—C5 | 1.523 (6) |
O3—C4 | 1.433 (2) | C4—C5' | 1.525 (6) |
O3—H3O | 0.842 (10) | C4—H4 | 0.9800 |
O4—C7 | 1.40 (3) | C5—C6 | 1.38 (2) |
O4—C7' | 1.46 (3) | C5—C7 | 1.518 (7) |
O4—H4O | 0.848 (10) | C6—H6 | 0.9300 |
O1W—H1W1 | 0.849 (10) | C7—H7A | 0.9700 |
O1W—H1W2 | 0.855 (10) | C7—H7B | 0.9700 |
N1—C1i | 1.507 (2) | C5'—C6' | 1.48 (3) |
N1—C1 | 1.507 (2) | C5'—C7' | 1.522 (7) |
N1—H1N | 0.862 (10) | C5'—H5' | 0.9800 |
C1—C6' | 1.514 (4) | C6'—H6'1 | 0.9700 |
C1—C2 | 1.530 (3) | C6'—H6'2 | 0.9700 |
C1—C6 | 1.554 (5) | C7'—H7'1 | 0.9700 |
C1—H1 | 0.9800 | C7'—H7'2 | 0.9700 |
C2—C3 | 1.520 (3) | | |
| | | |
C2—O1—H1O | 104.5 (18) | O3—C4—H4 | 107.2 |
C3—O2—H2O | 111 (2) | C3—C4—H4 | 107.2 |
C4—O3—H3O | 110 (2) | C5—C4—H4 | 107.2 |
C7—O4—H4O | 109 (2) | C5'—C4—H4 | 116.1 |
C7'—O4—H4O | 117 (3) | C6—C5—C7 | 121.5 (14) |
H1W1—O1W—H1W2 | 109.3 (15) | C6—C5—C4 | 121.0 (15) |
C1i—N1—C1 | 116.4 (2) | C7—C5—C4 | 117.4 (19) |
C1i—N1—H1N | 108 (3) | C5—C6—C1 | 120.7 (7) |
C1—N1—H1N | 108 (3) | C5—C6—H6 | 119.7 |
N1—C1—C6' | 122.3 (2) | C1—C6—H6 | 119.7 |
N1—C1—C2 | 110.54 (14) | O4—C7—C5 | 108.0 (18) |
C6'—C1—C2 | 107.5 (3) | O4—C7—H7A | 110.1 |
N1—C1—C6 | 100.0 (2) | C5—C7—H7A | 110.1 |
C2—C1—C6 | 115.5 (2) | O4—C7—H7B | 110.1 |
N1—C1—H1 | 110.1 | C5—C7—H7B | 110.1 |
C6'—C1—H1 | 95.1 | H7A—C7—H7B | 108.4 |
C2—C1—H1 | 110.1 | C6'—C5'—C7' | 109.2 (16) |
C6—C1—H1 | 110.1 | C6'—C5'—C4 | 109.3 (15) |
O1—C2—C3 | 108.23 (15) | C7'—C5'—C4 | 107.7 (18) |
O1—C2—C1 | 109.79 (15) | C6'—C5'—H5' | 110.2 |
C3—C2—C1 | 113.72 (14) | C7'—C5'—H5' | 110.2 |
O1—C2—H2 | 108.3 | C4—C5'—H5' | 110.2 |
C3—C2—H2 | 108.3 | C5'—C6'—C1 | 111.6 (8) |
C1—C2—H2 | 108.3 | C5'—C6'—H6'1 | 109.3 |
O2—C3—C2 | 109.95 (14) | C1—C6'—H6'1 | 109.3 |
O2—C3—C4 | 108.42 (15) | C5'—C6'—H6'2 | 109.3 |
C2—C3—C4 | 109.50 (16) | C1—C6'—H6'2 | 109.3 |
O2—C3—H3 | 109.6 | H6'1—C6'—H6'2 | 108.0 |
C2—C3—H3 | 109.6 | O4—C7'—C5' | 111.0 (18) |
C4—C3—H3 | 109.6 | O4—C7'—H7'1 | 109.4 |
O3—C4—C3 | 110.37 (16) | C5'—C7'—H7'1 | 109.4 |
O3—C4—C5 | 110.9 (11) | O4—C7'—H7'2 | 109.4 |
C3—C4—C5 | 113.7 (9) | C5'—C7'—H7'2 | 109.4 |
O3—C4—C5' | 109.3 (11) | H7'1—C7'—H7'2 | 108.0 |
C3—C4—C5' | 106.6 (9) | | |
| | | |
C1i—N1—C1—C6' | 97.1 (3) | C5'—C4—C5—C7 | 116 (14) |
C1i—N1—C1—C2 | −134.84 (15) | C7—C5—C6—C1 | 172.5 (16) |
C1i—N1—C1—C6 | 103.0 (2) | C4—C5—C6—C1 | −5 (2) |
N1—C1—C2—O1 | 38.48 (19) | N1—C1—C6—C5 | 120.5 (13) |
C6'—C1—C2—O1 | 174.2 (2) | C6'—C1—C6—C5 | −72.2 (15) |
C6—C1—C2—O1 | 151.1 (2) | C2—C1—C6—C5 | 1.9 (13) |
N1—C1—C2—C3 | −82.93 (18) | C7'—O4—C7—C5 | −51 (11) |
C6'—C1—C2—C3 | 52.8 (3) | C6—C5—C7—O4 | −6 (3) |
C6—C1—C2—C3 | 29.6 (3) | C4—C5—C7—O4 | 172.0 (15) |
O1—C2—C3—O2 | 62.20 (19) | O3—C4—C5'—C6' | 176.0 (9) |
C1—C2—C3—O2 | −175.52 (15) | C3—C4—C5'—C6' | −64.7 (14) |
O1—C2—C3—C4 | −178.77 (15) | C5—C4—C5'—C6' | 75 (13) |
C1—C2—C3—C4 | −56.5 (2) | O3—C4—C5'—C7' | 57.5 (19) |
O2—C3—C4—O3 | −61.78 (19) | C3—C4—C5'—C7' | 176.9 (15) |
C2—C3—C4—O3 | 178.25 (14) | C5—C4—C5'—C7' | −44 (12) |
O2—C3—C4—C5 | 172.8 (12) | C7'—C5'—C6'—C1 | −177.4 (13) |
C2—C3—C4—C5 | 52.9 (12) | C4—C5'—C6'—C1 | 65.0 (14) |
O2—C3—C4—C5' | 179.6 (11) | N1—C1—C6'—C5' | 72.7 (7) |
C2—C3—C4—C5' | 59.6 (11) | C2—C1—C6'—C5' | −56.6 (7) |
O3—C4—C5—C6 | −148.0 (16) | C6—C1—C6'—C5' | 57.9 (11) |
C3—C4—C5—C6 | −23 (2) | C7—O4—C7'—C5' | 109 (12) |
C5'—C4—C5—C6 | −66 (12) | C6'—C5'—C7'—O4 | 53.3 (19) |
O3—C4—C5—C7 | 34 (2) | C4—C5'—C7'—O4 | 171.9 (15) |
C3—C4—C5—C7 | 159.2 (15) | | |
Symmetry code: (i) y+1, x−1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1W | 0.85 (1) | 1.89 (1) | 2.715 (2) | 168 (3) |
O2—H2O···O1Wii | 0.85 (1) | 1.96 (1) | 2.781 (2) | 162 (3) |
O3—H3O···O2iii | 0.85 (1) | 1.91 (1) | 2.750 (2) | 173 (3) |
O4—H4O···Cl1 | 0.85 (1) | 2.29 (1) | 3.137 (1) | 176 (3) |
N1—H1N···O1 | 0.85 (1) | 2.19 (3) | 2.699 (2) | 118 (3) |
N1—H1N···Cl1iv | 0.85 (1) | 2.69 (1) | 3.111 (2) | 112 (1) |
O1W—H1W1···O3v | 0.85 (1) | 1.97 (1) | 2.799 (2) | 166 (2) |
O1W—H1W2···O4vi | 0.85 (1) | 1.87 (1) | 2.726 (2) | 175 (3) |
Symmetry codes: (ii) x−1/2, −y+1/2, −z+5/4; (iii) y, x, −z+1; (iv) y+1/2, −x+1/2, z+1/4; (v) y+1, x, −z+1; (vi) y+1/2, −x+3/2, z+1/4. |
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