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The title compound, C17H33NO7, contains two six-membered rings which adopt chair conformations. The molecular packing is governed by intermolecular O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001564/dn6110sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001564/dn6110Isup2.hkl
Contains datablock I

CCDC reference: 213674

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.087
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.59 Ratio PLAT417_ALERT_2_B Short Inter D-H..H-D H3 .. H6D = 1.72 Ang.
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.61 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9B PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C15B PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc. PLAT417_ALERT_2_C Short Inter D-H..H-D H1 .. H6 = 2.11 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O7 = 2.66 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 11.10 Deg. C9B -C7 -C9 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 14.30 Deg. C17B -C12 -C17A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.80 Deg. C15B -C14 -C15A 1.555 1.555 1.555
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 28.74 From the CIF: _reflns_number_total 2590 Count of symmetry unique reflns 2589 Completeness (_total/calc) 100.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL, ORTEPII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

1-Cyclohexylmethoxymethyl-5-[2-hydroxy-1-(hydroxymethyl)ethylamino]cyclohexane- 1,2,3,4-tetraol top
Crystal data top
C17H33NO7F(000) = 396
Mr = 363.44Dx = 1.309 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 33 reflections
a = 8.437 (2) Åθ = 4.7–15.2°
b = 6.853 (1) ŵ = 0.10 mm1
c = 16.011 (3) ÅT = 296 K
β = 94.88 (2)°Chunk, colorless
V = 922.4 (3) Å30.56 × 0.50 × 0.20 mm
Z = 2
Data collection top
Siemens P4
diffractometer
Rint = 0.011
Radiation source: fine-focus sealed tubeθmax = 28.7°, θmin = 1.3°
Graphite monochromatorh = 1011
ω scansk = 89
4872 measured reflectionsl = 2121
2590 independent reflections3 standard reflections every 97 reflections
2131 reflections with I > 2σ(I) intensity decay: 2.5%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0556P)2]
where P = (Fo2 + 2Fc2)/3
2590 reflections(Δ/σ)max = 0.001
285 parametersΔρmax = 0.21 e Å3
89 restraintsΔρmin = 0.13 e Å3
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 > 2σ(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
xyzUiso*/UeqOcc. (<1)
O10.57755 (13)0.5097 (2)0.85655 (7)0.0342 (3)
H10.51620.41990.86430.051*
O20.83954 (15)0.5761 (2)0.97494 (8)0.0358 (3)
H20.92590.62760.96970.054*
O30.86498 (14)0.2105 (2)1.05207 (7)0.0366 (3)
H30.81580.20781.09410.055*
O40.65721 (15)0.0827 (2)0.98326 (8)0.0377 (3)
H40.68220.19440.97160.057*
O50.74156 (16)0.6273 (2)0.71577 (8)0.0414 (3)
O60.32776 (19)0.2435 (3)0.81935 (10)0.0561 (4)
H60.40550.31560.82500.084*0.71
H6D0.22840.23770.80590.084*0.29
N0.47253 (16)0.1282 (2)0.86054 (9)0.0296 (3)
H1N0.449 (2)0.053 (4)0.8983 (12)0.035*
C10.73086 (19)0.4315 (3)0.84219 (10)0.0283 (4)
C20.8274 (2)0.3994 (3)0.92724 (11)0.0287 (4)
H2A0.93500.35850.91630.034*
C30.75650 (19)0.2428 (3)0.97979 (10)0.0276 (4)
H3A0.65400.28740.99720.033*
C40.73413 (19)0.0520 (3)0.93179 (10)0.0289 (4)
H4A0.83930.00000.92230.035*
C50.63877 (18)0.0778 (3)0.84656 (10)0.0278 (4)
H50.63950.04550.81560.033*
C60.7144 (2)0.2375 (3)0.79565 (10)0.0304 (4)
H6A0.81880.19440.78230.036*
H6B0.64960.25650.74330.036*
C80.3470 (2)0.1097 (3)0.75441 (12)0.0398 (5)
H8A0.25780.12070.71220.048*
H8B0.44330.14040.72810.048*
C70.3568 (2)0.0989 (3)0.78791 (11)0.0329 (4)
H7A0.389 (2)0.179 (4)0.7408 (13)0.039*
C90.1945 (6)0.1636 (14)0.8135 (6)0.0358 (12)0.71
H9A0.11580.14310.76660.043*0.71
H9B0.16590.08150.85920.043*0.71
O70.1882 (2)0.3540 (4)0.83795 (15)0.0508 (6)0.71
H70.25420.37290.87770.076*0.71
C9B0.197 (2)0.190 (5)0.7990 (18)0.071 (10)0.29
H9B10.21310.31580.82610.085*0.29
H9B20.14150.21240.74420.085*0.29
O7B0.1015 (6)0.0784 (11)0.8455 (3)0.0560 (15)0.29
H7B0.14980.05160.89060.084*0.29
C100.8208 (2)0.5817 (3)0.79499 (11)0.0343 (4)
H10A0.83330.69990.82830.041*
H10B0.92610.53190.78710.041*
C110.8306 (3)0.7701 (4)0.67517 (13)0.0460 (5)
H11A0.93440.71740.66600.055*
H11B0.84640.88360.71110.055*
C120.7475 (3)0.8309 (4)0.59259 (13)0.0474 (5)
H120.638 (3)0.864 (4)0.6018 (15)0.057*
C130.8309 (4)1.0063 (4)0.55844 (15)0.0643 (7)
H13A0.82401.11470.59700.077*
H13B0.94250.97540.55590.077*
C140.7622 (4)1.0693 (5)0.47234 (17)0.0796 (9)
H14A0.81831.18300.45400.096*
H14B0.65061.10220.47350.096*
C15A0.782 (3)0.900 (2)0.4133 (7)0.093 (5)0.52
H15A0.73590.93400.35760.112*0.52
H15B0.89390.87370.41000.112*0.52
C16A0.7011 (14)0.717 (2)0.4425 (8)0.090 (4)0.52
H16A0.58700.73830.43860.108*0.52
H16B0.72200.61000.40530.108*0.52
C17A0.756 (2)0.6601 (17)0.5313 (6)0.062 (3)0.52
H17A0.86530.61380.53310.075*0.52
H17B0.69090.55380.54880.075*0.52
C15B0.727 (3)0.911 (2)0.4095 (9)0.099 (7)0.48
H15C0.82620.85770.39280.119*0.48
H15D0.66830.96440.36010.119*0.48
C16B0.6301 (16)0.748 (2)0.4454 (8)0.087 (4)0.48
H16C0.52470.79540.45450.105*0.48
H16D0.61850.64030.40590.105*0.48
C17B0.713 (2)0.6764 (18)0.5281 (8)0.068 (4)0.48
H17C0.64730.57730.55110.081*0.48
H17D0.81280.61500.51670.081*0.48
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0263 (6)0.0342 (7)0.0429 (7)0.0076 (6)0.0068 (5)0.0042 (6)
O20.0350 (6)0.0303 (7)0.0419 (7)0.0038 (6)0.0024 (5)0.0056 (6)
O30.0316 (6)0.0472 (8)0.0300 (6)0.0064 (6)0.0034 (5)0.0020 (6)
O40.0443 (7)0.0290 (7)0.0407 (7)0.0005 (6)0.0084 (6)0.0056 (6)
O50.0435 (7)0.0462 (9)0.0346 (6)0.0057 (7)0.0033 (5)0.0086 (7)
O60.0515 (9)0.0469 (9)0.0716 (10)0.0055 (8)0.0159 (8)0.0077 (9)
N0.0231 (6)0.0364 (9)0.0295 (7)0.0012 (6)0.0042 (5)0.0003 (7)
C10.0235 (7)0.0306 (9)0.0314 (8)0.0038 (7)0.0055 (6)0.0014 (7)
C20.0246 (7)0.0280 (9)0.0339 (9)0.0022 (7)0.0045 (6)0.0025 (8)
C30.0217 (7)0.0312 (9)0.0297 (8)0.0045 (7)0.0007 (6)0.0003 (7)
C40.0262 (8)0.0277 (9)0.0330 (8)0.0042 (7)0.0039 (7)0.0014 (7)
C50.0236 (7)0.0289 (9)0.0307 (8)0.0021 (7)0.0020 (6)0.0038 (8)
C60.0262 (8)0.0361 (10)0.0294 (8)0.0032 (8)0.0052 (6)0.0001 (8)
C80.0328 (9)0.0498 (13)0.0364 (10)0.0003 (9)0.0009 (8)0.0072 (9)
C70.0260 (8)0.0418 (11)0.0307 (8)0.0017 (8)0.0007 (7)0.0008 (9)
C90.020 (2)0.050 (3)0.037 (3)0.0037 (17)0.0009 (14)0.005 (2)
O70.0418 (11)0.0456 (13)0.0646 (14)0.0157 (11)0.0024 (10)0.0064 (12)
C9B0.053 (9)0.10 (2)0.055 (11)0.010 (9)0.004 (6)0.001 (9)
O7B0.041 (3)0.077 (4)0.050 (3)0.008 (3)0.006 (2)0.006 (3)
C100.0330 (8)0.0349 (10)0.0354 (9)0.0006 (8)0.0045 (7)0.0049 (8)
C110.0536 (12)0.0467 (12)0.0392 (10)0.0076 (11)0.0129 (9)0.0054 (10)
C120.0571 (13)0.0465 (13)0.0398 (11)0.0016 (11)0.0119 (9)0.0074 (10)
C130.0957 (19)0.0518 (15)0.0470 (12)0.0107 (15)0.0156 (13)0.0101 (12)
C140.114 (2)0.0678 (19)0.0572 (14)0.0082 (19)0.0061 (15)0.0257 (16)
C15A0.142 (10)0.104 (9)0.032 (4)0.011 (6)0.005 (5)0.013 (5)
C16A0.129 (11)0.084 (6)0.053 (4)0.027 (7)0.014 (5)0.005 (4)
C17A0.104 (9)0.050 (4)0.031 (3)0.007 (4)0.004 (3)0.005 (3)
C15B0.171 (19)0.078 (8)0.046 (5)0.024 (8)0.004 (6)0.021 (5)
C16B0.129 (10)0.086 (7)0.042 (4)0.039 (7)0.019 (5)0.020 (5)
C17B0.094 (9)0.052 (5)0.056 (6)0.008 (5)0.008 (4)0.016 (4)
Geometric parameters (Å, º) top
O1—C11.4364 (19)O7—H70.8200
O1—H10.8200C9B—O7B1.37 (2)
O2—C21.431 (2)C9B—H9B10.9700
O2—H20.8200C9B—H9B20.9700
O3—C31.430 (2)O7B—H7B0.8200
O3—H30.8200C10—H10A0.9700
O4—C41.429 (2)C10—H10B0.9700
O4—H40.8200C11—C121.502 (3)
O5—C101.417 (2)C11—H11A0.9700
O5—C111.424 (3)C11—H11B0.9700
O6—C81.406 (3)C12—C17B1.491 (11)
O6—H60.8200C12—C131.518 (4)
O6—H6D0.8484C12—C17A1.534 (9)
N—C71.467 (2)C12—H120.98 (2)
N—C51.480 (2)C13—C141.512 (4)
N—H1N0.83 (2)C13—H13A0.9700
C1—C101.518 (3)C13—H13B0.9700
C1—C61.525 (3)C14—C15B1.494 (11)
C1—C21.542 (2)C14—C15A1.516 (12)
C2—C31.517 (3)C14—H14A0.9700
C2—H2A0.9800C14—H14B0.9700
C3—C41.521 (3)C15A—C16A1.516 (12)
C3—H3A0.9800C15A—H15A0.9700
C4—C51.534 (2)C15A—H15B0.9700
C4—H4A0.9800C16A—C17A1.509 (11)
C5—C61.535 (3)C16A—H16A0.9700
C5—H50.9800C16A—H16B0.9700
C6—H6A0.9700C17A—H17A0.9700
C6—H6B0.9700C17A—H17B0.9700
C8—C71.527 (3)C15B—C16B1.526 (12)
C8—H8A0.9700C15B—H15C0.9700
C8—H8B0.9700C15B—H15D0.9700
C7—C9B1.513 (15)C16B—C17B1.525 (12)
C7—C91.528 (5)C16B—H16C0.9700
C7—H7A0.99 (2)C16B—H16D0.9700
C9—O71.364 (9)C17B—H17C0.9700
C9—H9A0.9700C17B—H17D0.9700
C9—H9B0.9700
C1—O1—H1109.5C9B—O7B—H7B109.5
C2—O2—H2109.5O5—C10—C1112.18 (15)
C3—O3—H3109.5O5—C10—H10A109.2
C4—O4—H4109.5C1—C10—H10A109.2
C10—O5—C11109.46 (14)O5—C10—H10B109.2
C8—O6—H6109.5C1—C10—H10B109.2
C8—O6—H6D87.5H10A—C10—H10B107.9
H6—O6—H6D145.1O5—C11—C12111.58 (18)
C7—N—C5115.07 (13)O5—C11—H11A109.3
C7—N—H1N107.9 (14)C12—C11—H11A109.3
C5—N—H1N104.6 (14)O5—C11—H11B109.3
O1—C1—C10108.79 (15)C12—C11—H11B109.3
O1—C1—C6110.94 (14)H11A—C11—H11B108.0
C10—C1—C6112.14 (13)C17B—C12—C11117.5 (6)
O1—C1—C2109.10 (13)C17B—C12—C13112.5 (7)
C10—C1—C2106.73 (13)C11—C12—C13109.9 (2)
C6—C1—C2109.03 (14)C17B—C12—C17A14.3 (14)
O2—C2—C3108.43 (13)C11—C12—C17A107.9 (6)
O2—C2—C1111.02 (14)C13—C12—C17A109.0 (6)
C3—C2—C1112.78 (14)C17B—C12—H1297.9 (18)
O2—C2—H2A108.2C11—C12—H12108.0 (14)
C3—C2—H2A108.2C13—C12—H12110.2 (17)
C1—C2—H2A108.2C17A—C12—H12111.8 (18)
O3—C3—C2107.63 (14)C14—C13—C12113.7 (3)
O3—C3—C4108.60 (15)C14—C13—H13A108.8
C2—C3—C4111.45 (13)C12—C13—H13A108.8
O3—C3—H3A109.7C14—C13—H13B108.8
C2—C3—H3A109.7C12—C13—H13B108.8
C4—C3—H3A109.7H13A—C13—H13B107.7
O4—C4—C3107.87 (13)C15B—C14—C13116.5 (8)
O4—C4—C5110.97 (14)C15B—C14—C15A17.8 (17)
C3—C4—C5112.54 (14)C13—C14—C15A107.3 (7)
O4—C4—H4A108.5C15B—C14—H14A117.1
C3—C4—H4A108.5C13—C14—H14A110.3
C5—C4—H4A108.5C15A—C14—H14A110.3
N—C5—C4108.93 (12)C15B—C14—H14B92.5
N—C5—C6110.85 (15)C13—C14—H14B110.3
C4—C5—C6110.15 (14)C15A—C14—H14B110.3
N—C5—H5109.0H14A—C14—H14B108.5
C4—C5—H5109.0C16A—C15A—C14111.4 (11)
C6—C5—H5109.0C16A—C15A—H15A109.3
C1—C6—C5112.76 (13)C14—C15A—H15A109.3
C1—C6—H6A109.0C16A—C15A—H15B109.3
C5—C6—H6A109.0C14—C15A—H15B109.3
C1—C6—H6B109.0H15A—C15A—H15B108.0
C5—C6—H6B109.0C17A—C16A—C15A113.2 (10)
H6A—C6—H6B107.8C17A—C16A—H16A108.9
O6—C8—C7110.91 (16)C15A—C16A—H16A108.9
O6—C8—H8A109.5C17A—C16A—H16B108.9
C7—C8—H8A109.5C15A—C16A—H16B108.9
O6—C8—H8B109.5H16A—C16A—H16B107.8
C7—C8—H8B109.5C16A—C17A—C12112.2 (10)
H8A—C8—H8B108.0C16A—C17A—H17A109.2
N—C7—C9B113.0 (12)C12—C17A—H17A109.2
N—C7—C8114.77 (16)C16A—C17A—H17B109.2
C9B—C7—C8113.9 (13)C12—C17A—H17B109.2
N—C7—C9107.4 (4)H17A—C17A—H17B107.9
C9B—C7—C911.1 (13)C14—C15B—C16B111.2 (10)
C8—C7—C9110.1 (4)C14—C15B—H15C109.4
N—C7—H7A108.6 (13)C16B—C15B—H15C109.4
C9B—C7—H7A99.9 (16)C14—C15B—H15D109.4
C8—C7—H7A105.0 (13)C16B—C15B—H15D109.4
C9—C7—H7A111.0 (13)H15C—C15B—H15D108.0
O7—C9—C7114.3 (5)C17B—C16B—C15B109.9 (11)
O7—C9—H9A108.7C17B—C16B—H16C109.7
C7—C9—H9A108.7C15B—C16B—H16C109.7
O7—C9—H9B108.7C17B—C16B—H16D109.7
C7—C9—H9B108.7C15B—C16B—H16D109.7
H9A—C9—H9B107.6H16C—C16B—H16D108.2
C9—O7—H7109.5C12—C17B—C16B115.0 (10)
O7B—C9B—C7113.8 (18)C12—C17B—H17C108.5
O7B—C9B—H9B1108.8C16B—C17B—H17C108.5
C7—C9B—H9B1108.8C12—C17B—H17D108.5
O7B—C9B—H9B2108.8C16B—C17B—H17D108.5
C7—C9B—H9B2108.8H17C—C17B—H17D107.5
H9B1—C9B—H9B2107.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N0.822.032.763 (2)148
O2—H2···O3i0.821.912.7264 (19)171
O3—H3···O6ii0.821.952.748 (2)166
O3—H3···O7iii0.822.663.067 (3)112
O4—H4···O2iv0.822.062.808 (2)152
O6—H6···O1iv0.821.922.729 (2)171
O6—H6D···O7B0.852.522.969 (6)114
N—H1N···O40.83 (2)2.32 (2)2.803 (2)117.3 (16)
O7—H7···O4ii0.822.313.074 (3)156
O7B—H7B···O2iii0.822.152.877 (5)147
O7B—H7B···O3iii0.822.523.008 (7)120
Symmetry codes: (i) x+2, y+1/2, z+2; (ii) x+1, y+1/2, z+2; (iii) x+1, y1/2, z+2; (iv) x, y1, z.
 

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