2-O-Monoalkyl isosorbide ethers with C8, C10, C12 and C14 chain lengths

Geburtig, F.; Vill, V.

doi:10.1107/S2056989020006647

2-O-Monoalkyl isosorbide ethers with C8, C10, C12 and C14 chain lengths

The crystal structures of 2-O-monooctyl isosorbide, 2-O-monodecyl isosorbide, 2-O-monododecyl isosorbide and 2-O-monotetradecyl isosorbide are reported. All four compounds crystallize in the chiral space group P2₁.

Keywords: crystal structure; isorbide; short-chain amphiphiles; carbohydrate derivate.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020006647/zq2253sup1.cif Contains datablocks iso-c8, iso-c10, iso-c12, iso-c14
	Chemdraw file https://doi.org/10.1107/S2056989020006647/zq2253Iso-C8sup6.cdx Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020006647/zq2253iso-c8sup10.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006647/zq2253iso-c8sup13.hkl Contains datablock iso-c8
	Chemdraw file https://doi.org/10.1107/S2056989020006647/zq2253Iso-C10sup7.cdx Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020006647/zq2253iso-c10sup11.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006647/zq2253iso-c10sup14.hkl Contains datablock iso-c10
	Chemdraw file https://doi.org/10.1107/S2056989020006647/zq2253Iso-C12sup8.cdx Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020006647/zq2253iso-c12sup12.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006647/zq2253iso-c12sup15.hkl Contains datablock iso-c12
	Chemdraw file https://doi.org/10.1107/S2056989020006647/zq2253Iso-C14sup9.cdx Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020006647/zq2253iso-c14sup13.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006647/zq2253iso-c14sup16.hkl Contains datablock iso-c14

CCDC references: 2004430; 2004429; 2004428; 2004427

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
Mean (C-C) = 0.004 Å
Mean (C-C) = 0.006 Å
Mean (C-C) = 0.005 Å
R factor = 0.042
wR factor = 0.110
Data-to-parameter ratio = 20.9

checkCIF/PLATON results

No syntax errors found



Datablock: iso-c8



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.700
           From the CIF: _refine_ls_abs_structure_Flack_su    0.500
PLAT411_ALERT_2_C Short Inter H...H Contact  H4A      ..H6A      .       2.10 Ang.
                                                   x,-1+y,z  =      1_545 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.500 Report
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             109.3 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             109.1 Degree
PLAT791_ALERT_4_G Model has Chirality at C2          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Sohnke SpGr)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.13 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: iso-c10



Alert level C
PLAT411_ALERT_2_C Short Inter H...H Contact  H4A      ..H6A      .       2.09 Ang.
                                                    x,1+y,z  =      1_565 Check

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             109.9 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             108.7 Degree
PLAT791_ALERT_4_G Model has Chirality at C2          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Sohnke SpGr)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: iso-c12



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.600
           From the CIF: _refine_ls_abs_structure_Flack_su    0.900
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.0 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00637 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H4A      ..H6B      .       2.11 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.577 Check
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         87 %
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  1.04A   From O4              0.44 eA-3

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.900 Report
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             109.2 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             108.6 Degree
PLAT791_ALERT_4_G Model has Chirality at C2          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Sohnke SpGr)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        122 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: iso-c14



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -1.200
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00539 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H4A      ..H6A      .       2.05 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.000 Report
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             109.1 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O3             108.9 Degree
PLAT791_ALERT_4_G Model has Chirality at C2          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Sohnke SpGr)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       1.02 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: BlS (Bruker, 2016) for iso-c8, iso-c14; CrysAlis PRO (Rigaku OD, 2020) for iso-c10, iso-c12. Cell refinement: SAINT (Bruker, 2019) for iso-c8, iso-c14; CrysAlis PRO (Rigaku OD, 2020) for iso-c10, iso-c12. Data reduction: SAINT (Bruker, 2019) for iso-c8, iso-c14; CrysAlis PRO (Rigaku OD, 2020) for iso-c10, iso-c12. Program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a) for iso-c8, iso-c14; SHELXT2018/2 (Sheldrick, 2015a) for iso-c10, iso-c12. For all structures, program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

6-(Octyloxy)hexahydrofuro[3,2-b]furan-3-ol (iso-c8) top

Crystal data top

C₁₄H₂₆O₄	F(000) = 284
M_r = 258.35	D_x = 1.218 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.0008 (13) Å	Cell parameters from 5399 reflections
b = 5.5112 (10) Å	θ = 3.0–27.7°
c = 18.544 (3) Å	µ = 0.09 mm⁻¹
β = 100.155 (4)°	T = 100 K
V = 704.3 (2) Å³	Plate, colourless
Z = 2	0.29 × 0.14 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	3128 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	R_int = 0.048
φ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: numerical (SADABS; Bruker, 2016)	h = −9→9
T_min = 0.604, T_max = 0.746	k = −7→7
16451 measured reflections	l = −24→24
3491 independent reflections

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)] = 0.042	w = 1/[σ²(F_o²) + (0.0584P)² + 0.0928P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.29 e Å⁻³
3491 reflections	Δρ_min = −0.22 e Å⁻³
167 parameters	Absolute structure: Flack x determined using 1274 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.7 (5)
Primary atom site location: dual

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	−0.3146 (2)	1.1240 (3)	0.46449 (9)	0.0206 (4)
H4	−0.204 (4)	1.202 (6)	0.4671 (15)	0.031*
O3	−0.2626 (2)	1.1015 (3)	0.66173 (9)	0.0223 (4)
C6	−0.3112 (3)	1.2324 (5)	0.59462 (13)	0.0202 (5)
H6A	−0.211534	1.356261	0.590200	0.024*
H6B	−0.438754	1.313362	0.591209	0.024*
C5	−0.3178 (3)	1.0391 (4)	0.53597 (12)	0.0175 (5)
H5	−0.439886	0.943600	0.534571	0.021*
C4	−0.1475 (3)	0.8769 (4)	0.56869 (12)	0.0162 (4)
H4A	−0.167151	0.705588	0.551189	0.019*
O1	0.0336 (2)	0.9757 (3)	0.55443 (8)	0.0173 (3)
C1	0.1401 (3)	1.0801 (4)	0.62113 (12)	0.0184 (5)
H1A	0.112653	1.255842	0.623537	0.022*
H1B	0.281444	1.057319	0.623838	0.022*
C2	0.0702 (3)	0.9457 (4)	0.68292 (12)	0.0178 (5)
H2	0.083366	1.047420	0.728187	0.021*
C3	−0.1426 (3)	0.8969 (4)	0.65068 (12)	0.0172 (4)
H3	−0.189743	0.744399	0.670946	0.021*
O2	0.1583 (2)	0.7144 (3)	0.69783 (9)	0.0196 (4)
C7	0.3524 (3)	0.7307 (5)	0.73806 (13)	0.0224 (5)
H7A	0.355169	0.837569	0.781134	0.027*
H7B	0.438704	0.801247	0.706650	0.027*
C8	0.4223 (3)	0.4806 (5)	0.76282 (13)	0.0207 (5)
H8A	0.421057	0.375583	0.719426	0.025*
H8B	0.332855	0.409170	0.792837	0.025*
C9	0.6279 (3)	0.4879 (5)	0.80782 (13)	0.0217 (5)
H9A	0.716491	0.559354	0.777433	0.026*
H9B	0.628485	0.595407	0.850628	0.026*
C10	0.7051 (3)	0.2392 (5)	0.83484 (12)	0.0197 (5)
H10A	0.625967	0.175594	0.869914	0.024*
H10B	0.691287	0.126099	0.792767	0.024*
C11	0.9172 (3)	0.2475 (5)	0.87199 (13)	0.0207 (5)
H11A	0.994196	0.323853	0.838152	0.025*
H11B	0.928797	0.351471	0.916094	0.025*
C12	1.0032 (3)	−0.0002 (4)	0.89449 (13)	0.0205 (5)
H12A	0.997027	−0.102242	0.850206	0.025*
H12B	0.923641	−0.079522	0.926877	0.025*
C13	1.2132 (3)	0.0131 (5)	0.93423 (13)	0.0234 (5)
H13A	1.290702	0.102721	0.903187	0.028*
H13B	1.217835	0.106071	0.980190	0.028*
C14	1.3052 (4)	−0.2343 (5)	0.95257 (15)	0.0286 (6)
H14A	1.306695	−0.324955	0.907209	0.043*
H14B	1.229830	−0.324164	0.983527	0.043*
H14C	1.438497	−0.213184	0.978793	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0132 (7)	0.0254 (9)	0.0228 (8)	−0.0035 (7)	0.0025 (6)	0.0041 (7)
O3	0.0213 (8)	0.0237 (9)	0.0231 (9)	0.0053 (7)	0.0074 (6)	−0.0009 (7)
C6	0.0159 (10)	0.0189 (11)	0.0264 (12)	0.0016 (9)	0.0056 (8)	0.0013 (10)
C5	0.0129 (9)	0.0176 (11)	0.0223 (11)	−0.0009 (8)	0.0040 (8)	0.0014 (9)
C4	0.0142 (10)	0.0113 (9)	0.0237 (11)	−0.0013 (8)	0.0053 (8)	0.0014 (8)
O1	0.0127 (7)	0.0192 (8)	0.0208 (8)	−0.0004 (6)	0.0052 (6)	0.0002 (6)
C1	0.0154 (10)	0.0162 (10)	0.0234 (11)	−0.0010 (8)	0.0030 (8)	−0.0009 (9)
C2	0.0169 (10)	0.0164 (11)	0.0198 (11)	−0.0006 (8)	0.0026 (8)	−0.0004 (9)
C3	0.0139 (10)	0.0139 (10)	0.0243 (12)	−0.0002 (8)	0.0045 (8)	0.0026 (9)
O2	0.0151 (7)	0.0172 (8)	0.0251 (9)	0.0001 (7)	−0.0002 (6)	0.0024 (7)
C7	0.0152 (10)	0.0240 (12)	0.0267 (12)	−0.0029 (10)	−0.0004 (8)	0.0034 (11)
C8	0.0157 (10)	0.0209 (11)	0.0244 (12)	−0.0006 (9)	0.0008 (8)	0.0020 (10)
C9	0.0160 (10)	0.0220 (11)	0.0260 (12)	−0.0025 (9)	0.0008 (8)	0.0028 (10)
C10	0.0155 (10)	0.0222 (11)	0.0211 (11)	−0.0011 (9)	0.0022 (8)	0.0006 (10)
C11	0.0154 (10)	0.0217 (11)	0.0252 (12)	−0.0005 (9)	0.0039 (8)	0.0011 (10)
C12	0.0159 (10)	0.0215 (11)	0.0242 (12)	−0.0005 (9)	0.0039 (8)	0.0010 (10)
C13	0.0154 (10)	0.0255 (13)	0.0287 (13)	0.0008 (9)	0.0023 (8)	0.0019 (10)
C14	0.0220 (12)	0.0317 (15)	0.0311 (14)	0.0053 (10)	0.0024 (10)	0.0023 (11)

Geometric parameters (Å, º) top

O4—H4	0.88 (3)	C7—C8	1.507 (3)
O4—C5	1.410 (3)	C8—H8A	0.9900
O3—C6	1.427 (3)	C8—H8B	0.9900
O3—C3	1.442 (3)	C8—C9	1.532 (3)
C6—H6A	0.9900	C9—H9A	0.9900
C6—H6B	0.9900	C9—H9B	0.9900
C6—C5	1.517 (3)	C9—C10	1.525 (3)
C5—H5	1.0000	C10—H10A	0.9900
C5—C4	1.527 (3)	C10—H10B	0.9900
C4—H4A	1.0000	C10—C11	1.524 (3)
C4—O1	1.447 (2)	C11—H11A	0.9900
C4—C3	1.519 (3)	C11—H11B	0.9900
O1—C1	1.446 (3)	C11—C12	1.520 (3)
C1—H1A	0.9900	C12—H12A	0.9900
C1—H1B	0.9900	C12—H12B	0.9900
C1—C2	1.516 (3)	C12—C13	1.526 (3)
C2—H2	1.0000	C13—H13A	0.9900
C2—C3	1.528 (3)	C13—H13B	0.9900
C2—O2	1.422 (3)	C13—C14	1.521 (4)
C3—H3	1.0000	C14—H14A	0.9800
O2—C7	1.433 (3)	C14—H14B	0.9800
C7—H7A	0.9900	C14—H14C	0.9800
C7—H7B	0.9900

C5—O4—H4	105.8 (19)	C8—C7—H7A	109.8
C6—O3—C3	109.08 (16)	C8—C7—H7B	109.8
O3—C6—H6A	110.9	C7—C8—H8A	109.3
O3—C6—H6B	110.9	C7—C8—H8B	109.3
O3—C6—C5	104.04 (19)	C7—C8—C9	111.45 (19)
H6A—C6—H6B	109.0	H8A—C8—H8B	108.0
C5—C6—H6A	110.9	C9—C8—H8A	109.3
C5—C6—H6B	110.9	C9—C8—H8B	109.3
O4—C5—C6	115.94 (19)	C8—C9—H9A	108.9
O4—C5—H5	107.8	C8—C9—H9B	108.9
O4—C5—C4	115.27 (17)	H9A—C9—H9B	107.7
C6—C5—H5	107.8	C10—C9—C8	113.56 (19)
C6—C5—C4	101.72 (17)	C10—C9—H9A	108.9
C4—C5—H5	107.8	C10—C9—H9B	108.9
C5—C4—H4A	111.8	C9—C10—H10A	109.1
O1—C4—C5	110.80 (18)	C9—C10—H10B	109.1
O1—C4—H4A	111.8	H10A—C10—H10B	107.8
O1—C4—C3	106.84 (17)	C11—C10—C9	112.47 (19)
C3—C4—C5	103.52 (17)	C11—C10—H10A	109.1
C3—C4—H4A	111.8	C11—C10—H10B	109.1
C1—O1—C4	109.25 (16)	C10—C11—H11A	108.8
O1—C1—H1A	110.7	C10—C11—H11B	108.8
O1—C1—H1B	110.7	H11A—C11—H11B	107.7
O1—C1—C2	105.42 (18)	C12—C11—C10	113.8 (2)
H1A—C1—H1B	108.8	C12—C11—H11A	108.8
C2—C1—H1A	110.7	C12—C11—H11B	108.8
C2—C1—H1B	110.7	C11—C12—H12A	109.0
C1—C2—H2	111.5	C11—C12—H12B	109.0
C1—C2—C3	102.28 (18)	C11—C12—C13	113.0 (2)
C3—C2—H2	111.5	H12A—C12—H12B	107.8
O2—C2—C1	113.45 (18)	C13—C12—H12A	109.0
O2—C2—H2	111.5	C13—C12—H12B	109.0
O2—C2—C3	106.12 (17)	C12—C13—H13A	108.9
O3—C3—C4	106.73 (17)	C12—C13—H13B	108.9
O3—C3—C2	111.02 (18)	H13A—C13—H13B	107.7
O3—C3—H3	111.4	C14—C13—C12	113.5 (2)
C4—C3—C2	104.65 (17)	C14—C13—H13A	108.9
C4—C3—H3	111.4	C14—C13—H13B	108.9
C2—C3—H3	111.4	C13—C14—H14A	109.5
C2—O2—C7	112.60 (18)	C13—C14—H14B	109.5
O2—C7—H7A	109.8	C13—C14—H14C	109.5
O2—C7—H7B	109.8	H14A—C14—H14B	109.5
O2—C7—C8	109.21 (19)	H14A—C14—H14C	109.5
H7A—C7—H7B	108.3	H14B—C14—H14C	109.5

O4—C5—C4—O1	44.0 (3)	C1—C2—C3—O3	−85.1 (2)
O4—C5—C4—C3	158.17 (18)	C1—C2—C3—C4	29.6 (2)
O3—C6—C5—O4	−164.56 (16)	C1—C2—O2—C7	76.8 (2)
O3—C6—C5—C4	−38.7 (2)	C2—O2—C7—C8	170.27 (18)
C6—O3—C3—C4	−10.3 (2)	C3—O3—C6—C5	31.1 (2)
C6—O3—C3—C2	103.2 (2)	C3—C4—O1—C1	−6.4 (2)
C6—C5—C4—O1	−82.3 (2)	C3—C2—O2—C7	−171.63 (17)
C6—C5—C4—C3	31.9 (2)	O2—C2—C3—O3	155.71 (17)
C5—C4—O1—C1	105.7 (2)	O2—C2—C3—C4	−89.5 (2)
C5—C4—C3—O3	−14.4 (2)	O2—C7—C8—C9	−178.64 (18)
C5—C4—C3—C2	−132.20 (18)	C7—C8—C9—C10	179.5 (2)
C4—O1—C1—C2	25.7 (2)	C8—C9—C10—C11	173.59 (19)
O1—C4—C3—O3	102.57 (19)	C9—C10—C11—C12	−175.6 (2)
O1—C4—C3—C2	−15.2 (2)	C10—C11—C12—C13	−177.75 (19)
O1—C1—C2—C3	−34.0 (2)	C11—C12—C13—C14	−176.2 (2)
O1—C1—C2—O2	79.9 (2)

6-(Decyloxy)hexahydrofuro[3,2-b]furan-3-ol (iso-c10) top

Crystal data top

C₁₆H₃₀O₄	F(000) = 316
M_r = 286.40	D_x = 1.192 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 6.9892 (2) Å	Cell parameters from 7114 reflections
b = 5.4888 (2) Å	θ = 4.2–76.2°
c = 20.8041 (6) Å	µ = 0.67 mm⁻¹
β = 91.302 (3)°	T = 100 K
V = 797.89 (4) Å³	Plate, colourless
Z = 2	0.44 × 0.16 × 0.08 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Atlas diffractometer	3028 reflections with I > 2σ(I)
Detector resolution: 10.4127 pixels mm^-1	R_int = 0.048
ω scans	θ_max = 76.9°, θ_min = 4.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −8→8
T_min = 0.590, T_max = 1.000	k = −6→6
17428 measured reflections	l = −26→26
3268 independent reflections

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)] = 0.042	w = 1/[σ²(F_o²) + (0.0741P)² + 0.1068P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.118	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.28 e Å⁻³
3268 reflections	Δρ_min = −0.21 e Å⁻³
185 parameters	Absolute structure: Flack x determined using 1249 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.18 (13)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	−0.2948 (2)	−0.2388 (4)	0.53094 (8)	0.0285 (4)
C5	−0.3362 (3)	−0.1528 (5)	0.46833 (11)	0.0261 (5)
H5	−0.457030	−0.055647	0.469645	0.031*
C6	−0.3615 (4)	−0.3478 (5)	0.41677 (12)	0.0285 (5)
H6A	−0.259150	−0.472001	0.420463	0.034*
H6B	−0.487258	−0.429298	0.420144	0.034*
O3	−0.3497 (3)	−0.2169 (4)	0.35754 (8)	0.0295 (4)
C3	−0.2217 (3)	−0.0132 (4)	0.36691 (11)	0.0253 (5)
H3	−0.279228	0.140392	0.349299	0.030*
C4	−0.1813 (3)	0.0076 (4)	0.43919 (11)	0.0236 (5)
H4A	−0.189557	0.179951	0.454433	0.028*
O1	0.0067 (2)	−0.0944 (3)	0.45089 (8)	0.0260 (4)
C1	0.0779 (3)	−0.1993 (4)	0.39222 (11)	0.0271 (5)
H1A	0.049214	−0.375810	0.390087	0.032*
H1B	0.217929	−0.176099	0.389610	0.032*
C2	−0.0268 (3)	−0.0629 (4)	0.33802 (11)	0.0253 (5)
H2	−0.039074	−0.165289	0.298387	0.030*
O2	0.0557 (3)	0.1676 (3)	0.32444 (8)	0.0274 (4)
C7	0.2266 (4)	0.1490 (5)	0.28830 (12)	0.0300 (5)
H7A	0.203111	0.045168	0.250013	0.036*
H7B	0.329320	0.072848	0.314992	0.036*
C8	0.2878 (4)	0.4002 (5)	0.26759 (12)	0.0278 (5)
H8A	0.310745	0.502828	0.306136	0.033*
H8B	0.183564	0.475990	0.241529	0.033*
C9	0.4700 (4)	0.3917 (5)	0.22816 (12)	0.0282 (5)
H9A	0.574428	0.319412	0.254840	0.034*
H9B	0.447666	0.284008	0.190571	0.034*
C10	0.5339 (4)	0.6413 (5)	0.20451 (11)	0.0266 (5)
H10A	0.546751	0.753028	0.241709	0.032*
H10B	0.434015	0.708219	0.174967	0.032*
C11	0.7238 (4)	0.6321 (5)	0.16973 (12)	0.0283 (5)
H11A	0.821209	0.554476	0.198301	0.034*
H11B	0.708077	0.528647	0.130987	0.034*
C12	0.7967 (4)	0.8820 (5)	0.14951 (12)	0.0282 (5)
H12A	0.813283	0.985547	0.188208	0.034*
H12B	0.699513	0.960098	0.120955	0.034*
C13	0.9863 (4)	0.8696 (5)	0.11464 (11)	0.0277 (5)
H13A	1.082709	0.789157	0.143048	0.033*
H13B	0.969014	0.767306	0.075754	0.033*
C14	1.0631 (4)	1.1179 (5)	0.09472 (12)	0.0282 (5)
H14A	0.963902	1.202929	0.068427	0.034*
H14B	1.088498	1.216908	0.133771	0.034*
C15	1.2459 (4)	1.1010 (5)	0.05646 (12)	0.0305 (6)
H15A	1.218905	1.007541	0.016575	0.037*
H15B	1.343110	1.009609	0.082066	0.037*
C16	1.3286 (4)	1.3485 (5)	0.03860 (13)	0.0346 (6)
H16A	1.233105	1.440762	0.013414	0.052*
H16B	1.443206	1.324933	0.013041	0.052*
H16C	1.362570	1.438813	0.077856	0.052*
H4	−0.190 (6)	−0.330 (8)	0.5295 (18)	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0223 (8)	0.0372 (9)	0.0258 (8)	0.0032 (8)	−0.0004 (6)	0.0043 (7)
C5	0.0219 (11)	0.0299 (12)	0.0262 (11)	0.0040 (9)	−0.0035 (9)	0.0016 (9)
C6	0.0253 (12)	0.0288 (11)	0.0312 (12)	−0.0026 (10)	−0.0021 (9)	0.0011 (10)
O3	0.0263 (9)	0.0364 (9)	0.0256 (8)	−0.0065 (7)	−0.0063 (6)	0.0005 (7)
C3	0.0208 (11)	0.0293 (11)	0.0256 (11)	−0.0001 (9)	−0.0046 (9)	0.0006 (9)
C4	0.0216 (11)	0.0232 (10)	0.0257 (10)	0.0045 (9)	−0.0040 (8)	0.0003 (9)
O1	0.0209 (8)	0.0315 (8)	0.0255 (8)	0.0018 (7)	−0.0049 (6)	0.0012 (6)
C1	0.0237 (11)	0.0293 (11)	0.0281 (11)	0.0021 (9)	−0.0021 (9)	0.0007 (9)
C2	0.0233 (12)	0.0286 (12)	0.0238 (10)	0.0005 (9)	−0.0020 (9)	−0.0007 (9)
O2	0.0249 (9)	0.0290 (8)	0.0284 (8)	−0.0002 (7)	0.0019 (7)	0.0017 (7)
C7	0.0255 (12)	0.0330 (12)	0.0316 (12)	0.0028 (10)	0.0030 (10)	0.0030 (10)
C8	0.0250 (12)	0.0313 (12)	0.0271 (11)	0.0019 (10)	0.0009 (9)	0.0009 (9)
C9	0.0246 (12)	0.0329 (12)	0.0270 (11)	0.0022 (10)	0.0005 (9)	0.0033 (10)
C10	0.0228 (12)	0.0322 (11)	0.0247 (10)	0.0011 (10)	−0.0022 (8)	0.0008 (9)
C11	0.0229 (12)	0.0324 (12)	0.0296 (11)	0.0007 (10)	−0.0015 (9)	0.0020 (10)
C12	0.0231 (12)	0.0319 (11)	0.0294 (11)	0.0010 (9)	0.0001 (9)	0.0012 (10)
C13	0.0224 (12)	0.0315 (12)	0.0290 (11)	0.0003 (9)	−0.0012 (9)	0.0015 (10)
C14	0.0225 (12)	0.0319 (12)	0.0302 (11)	−0.0008 (10)	−0.0016 (9)	−0.0008 (10)
C15	0.0250 (13)	0.0344 (13)	0.0320 (12)	−0.0007 (10)	−0.0003 (10)	0.0019 (10)
C16	0.0304 (13)	0.0398 (15)	0.0337 (12)	−0.0064 (11)	0.0006 (10)	0.0019 (11)

Geometric parameters (Å, º) top

O4—C5	1.409 (3)	C8—C9	1.531 (3)
O4—H4	0.89 (4)	C9—H9A	0.9900
C5—H5	1.0000	C9—H9B	0.9900
C5—C6	1.523 (3)	C9—C10	1.526 (3)
C5—C4	1.531 (3)	C10—H10A	0.9900
C6—H6A	0.9900	C10—H10B	0.9900
C6—H6B	0.9900	C10—C11	1.527 (3)
C6—O3	1.430 (3)	C11—H11A	0.9900
O3—C3	1.442 (3)	C11—H11B	0.9900
C3—H3	1.0000	C11—C12	1.526 (3)
C3—C4	1.528 (3)	C12—H12A	0.9900
C3—C2	1.526 (3)	C12—H12B	0.9900
C4—H4A	1.0000	C12—C13	1.527 (3)
C4—O1	1.444 (3)	C13—H13A	0.9900
O1—C1	1.448 (3)	C13—H13B	0.9900
C1—H1A	0.9900	C13—C14	1.525 (3)
C1—H1B	0.9900	C14—H14A	0.9900
C1—C2	1.526 (3)	C14—H14B	0.9900
C2—H2	1.0000	C14—C15	1.524 (3)
C2—O2	1.422 (3)	C15—H15A	0.9900
O2—C7	1.429 (3)	C15—H15B	0.9900
C7—H7A	0.9900	C15—C16	1.526 (4)
C7—H7B	0.9900	C16—H16A	0.9800
C7—C8	1.510 (4)	C16—H16B	0.9800
C8—H8A	0.9900	C16—H16C	0.9800
C8—H8B	0.9900

C5—O4—H4	108 (2)	C9—C8—H8A	109.3
O4—C5—H5	108.0	C9—C8—H8B	109.3
O4—C5—C6	115.7 (2)	C8—C9—H9A	108.9
O4—C5—C4	115.25 (19)	C8—C9—H9B	108.9
C6—C5—H5	108.0	H9A—C9—H9B	107.7
C6—C5—C4	101.37 (18)	C10—C9—C8	113.5 (2)
C4—C5—H5	108.0	C10—C9—H9A	108.9
C5—C6—H6A	110.9	C10—C9—H9B	108.9
C5—C6—H6B	110.9	C9—C10—H10A	109.0
H6A—C6—H6B	108.9	C9—C10—H10B	109.0
O3—C6—C5	104.2 (2)	C9—C10—C11	112.8 (2)
O3—C6—H6A	110.9	H10A—C10—H10B	107.8
O3—C6—H6B	110.9	C11—C10—H10A	109.0
C6—O3—C3	108.71 (18)	C11—C10—H10B	109.0
O3—C3—H3	111.2	C10—C11—H11A	108.8
O3—C3—C4	106.92 (19)	C10—C11—H11B	108.8
O3—C3—C2	111.40 (19)	H11A—C11—H11B	107.7
C4—C3—H3	111.2	C12—C11—C10	113.6 (2)
C2—C3—H3	111.2	C12—C11—H11A	108.8
C2—C3—C4	104.72 (18)	C12—C11—H11B	108.8
C5—C4—H4A	111.8	C11—C12—H12A	109.0
C3—C4—C5	103.31 (19)	C11—C12—H12B	109.0
C3—C4—H4A	111.8	C11—C12—C13	113.0 (2)
O1—C4—C5	111.05 (19)	H12A—C12—H12B	107.8
O1—C4—C3	106.51 (18)	C13—C12—H12A	109.0
O1—C4—H4A	111.8	C13—C12—H12B	109.0
C4—O1—C1	109.92 (17)	C12—C13—H13A	108.8
O1—C1—H1A	110.7	C12—C13—H13B	108.8
O1—C1—H1B	110.7	H13A—C13—H13B	107.7
O1—C1—C2	105.05 (18)	C14—C13—C12	113.8 (2)
H1A—C1—H1B	108.8	C14—C13—H13A	108.8
C2—C1—H1A	110.7	C14—C13—H13B	108.8
C2—C1—H1B	110.7	C13—C14—H14A	109.0
C3—C2—H2	111.4	C13—C14—H14B	109.0
C1—C2—C3	102.34 (18)	H14A—C14—H14B	107.8
C1—C2—H2	111.4	C15—C14—C13	113.1 (2)
O2—C2—C3	106.81 (18)	C15—C14—H14A	109.0
O2—C2—C1	113.20 (19)	C15—C14—H14B	109.0
O2—C2—H2	111.4	C14—C15—H15A	108.9
C2—O2—C7	112.85 (19)	C14—C15—H15B	108.9
O2—C7—H7A	109.8	C14—C15—C16	113.6 (2)
O2—C7—H7B	109.8	H15A—C15—H15B	107.7
O2—C7—C8	109.3 (2)	C16—C15—H15A	108.9
H7A—C7—H7B	108.3	C16—C15—H15B	108.9
C8—C7—H7A	109.8	C15—C16—H16A	109.5
C8—C7—H7B	109.8	C15—C16—H16B	109.5
C7—C8—H8A	109.3	C15—C16—H16C	109.5
C7—C8—H8B	109.3	H16A—C16—H16B	109.5
C7—C8—C9	111.7 (2)	H16A—C16—H16C	109.5
H8A—C8—H8B	107.9	H16B—C16—H16C	109.5

O4—C5—C6—O3	−164.89 (19)	C4—C3—C2—O2	−89.3 (2)
O4—C5—C4—C3	157.97 (19)	C4—O1—C1—C2	25.1 (2)
O4—C5—C4—O1	44.1 (3)	O1—C1—C2—C3	−33.7 (2)
C5—C6—O3—C3	31.7 (2)	O1—C1—C2—O2	80.9 (2)
C5—C4—O1—C1	106.0 (2)	C1—C2—O2—C7	76.9 (2)
C6—C5—C4—C3	32.2 (2)	C2—C3—C4—C5	−132.86 (19)
C6—C5—C4—O1	−81.6 (2)	C2—C3—C4—O1	−15.8 (2)
C6—O3—C3—C4	−10.6 (2)	C2—O2—C7—C8	171.6 (2)
C6—O3—C3—C2	103.3 (2)	O2—C7—C8—C9	−179.61 (19)
O3—C3—C4—C5	−14.6 (2)	C7—C8—C9—C10	178.3 (2)
O3—C3—C4—O1	102.5 (2)	C8—C9—C10—C11	175.6 (2)
O3—C3—C2—C1	−85.4 (2)	C9—C10—C11—C12	−176.2 (2)
O3—C3—C2—O2	155.46 (18)	C10—C11—C12—C13	−179.8 (2)
C3—C4—O1—C1	−5.8 (2)	C11—C12—C13—C14	−179.3 (2)
C3—C2—O2—C7	−171.21 (18)	C12—C13—C14—C15	−176.5 (2)
C4—C5—C6—O3	−39.5 (2)	C13—C14—C15—C16	−177.7 (2)
C4—C3—C2—C1	29.9 (2)

6-(Dodecyloxy)hexahydrofuro[3,2-b]furan-3-ol (iso-c12) top

Crystal data top

C₁₈H₃₄O₄	F(000) = 348
M_r = 314.45	D_x = 1.172 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.0250 (5) Å	Cell parameters from 3996 reflections
b = 5.4674 (5) Å	θ = 3.5–28.5°
c = 23.377 (2) Å	µ = 0.08 mm⁻¹
β = 97.051 (9)°	T = 100 K
V = 891.08 (14) Å³	Plate, colourless
Z = 2	0.37 × 0.08 × 0.03 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Atlas diffractometer	3638 reflections with I > 2σ(I)
Detector resolution: 5.2063 pixels mm^-1	R_int = 0.089
ω scans	θ_max = 29.5°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −9→9
T_min = 0.534, T_max = 1.000	k = −7→7
20988 measured reflections	l = −31→31
4546 independent reflections

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)] = 0.082	w = 1/[σ²(F_o²) + (0.0818P)² + 0.8491P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.202	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.50 e Å⁻³
4546 reflections	Δρ_min = −0.38 e Å⁻³
203 parameters	Absolute structure: Flack x determined using 1143 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.6 (9)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	−0.3077 (4)	−0.3567 (6)	0.47225 (13)	0.0195 (7)
C5	−0.3215 (5)	−0.2711 (8)	0.52867 (18)	0.0158 (9)
H5	−0.439260	−0.174098	0.527443	0.019*
C6	−0.3266 (6)	−0.4653 (9)	0.57474 (19)	0.0174 (9)
H6A	−0.451597	−0.542957	0.571783	0.021*
H6B	−0.229956	−0.589455	0.571468	0.021*
O3	−0.2875 (4)	−0.3345 (7)	0.62790 (13)	0.0208 (7)
C3	−0.1630 (5)	−0.1300 (8)	0.61918 (19)	0.0159 (9)
H3	−0.210764	0.021798	0.634561	0.019*
C4	−0.1536 (5)	−0.1104 (8)	0.55496 (18)	0.0140 (8)
H4A	−0.167596	0.059104	0.541499	0.017*
O1	0.0281 (4)	−0.2142 (6)	0.54414 (12)	0.0153 (6)
C1	0.1227 (5)	−0.3212 (9)	0.59724 (17)	0.0170 (9)
H1A	0.260627	−0.301348	0.599673	0.020*
H1B	0.093479	−0.494261	0.599072	0.020*
C2	0.0441 (5)	−0.1834 (7)	0.64566 (19)	0.0136 (8)
H2	0.047254	−0.284334	0.680410	0.016*
O2	0.1320 (4)	0.0484 (6)	0.65820 (13)	0.0166 (7)
C7	0.3182 (6)	0.0286 (9)	0.6908 (2)	0.0188 (9)
H7A	0.406758	−0.047907	0.667560	0.023*
H7B	0.310862	−0.072266	0.724628	0.023*
C8	0.3891 (6)	0.2810 (8)	0.7090 (2)	0.0166 (9)
H8A	0.298790	0.357484	0.731649	0.020*
H8B	0.396366	0.380691	0.674985	0.020*
C9	0.5881 (6)	0.2697 (9)	0.74473 (19)	0.0175 (9)
H9A	0.580593	0.166828	0.778182	0.021*
H9B	0.678027	0.194711	0.721704	0.021*
C10	0.6637 (5)	0.5215 (9)	0.76483 (19)	0.0160 (9)
H10A	0.580027	0.590708	0.790675	0.019*
H10B	0.660987	0.628991	0.731717	0.019*
C11	0.8693 (6)	0.5098 (9)	0.7959 (2)	0.0165 (9)
H11A	0.870743	0.406446	0.829691	0.020*
H11B	0.951671	0.434785	0.770482	0.020*
C12	0.9500 (6)	0.7609 (8)	0.8145 (2)	0.0172 (9)
H12A	0.865418	0.837972	0.838936	0.021*
H12B	0.952258	0.862509	0.780571	0.021*
C13	1.1527 (6)	0.7484 (8)	0.8471 (2)	0.0170 (9)
H13A	1.149900	0.648491	0.881296	0.020*
H13B	1.236680	0.668910	0.822859	0.020*
C14	1.2354 (6)	0.9980 (9)	0.8651 (2)	0.0183 (9)
H14A	1.151432	1.077765	0.889286	0.022*
H14B	1.238637	1.097924	0.830894	0.022*
C15	1.4371 (6)	0.9839 (9)	0.8976 (2)	0.0191 (10)
H15A	1.433404	0.884511	0.931853	0.023*
H15B	1.520532	0.902806	0.873456	0.023*
C16	1.5227 (6)	1.2328 (9)	0.9156 (2)	0.0207 (10)
H16A	1.437411	1.316001	0.938848	0.025*
H16B	1.530016	1.330526	0.881305	0.025*
C17	1.7225 (6)	1.2177 (10)	0.9498 (2)	0.0231 (11)
H17A	1.714132	1.126633	0.984997	0.028*
H17B	1.806347	1.127749	0.927284	0.028*
C18	1.8111 (7)	1.4663 (11)	0.9652 (2)	0.0277 (11)
H18A	1.826747	1.554178	0.930507	0.042*
H18B	1.933962	1.444704	0.987558	0.042*
H18C	1.728567	1.557221	0.987212	0.042*
H4	−0.207 (9)	−0.459 (13)	0.475 (2)	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0071 (12)	0.0232 (18)	0.0277 (16)	0.0025 (13)	0.0006 (11)	−0.0055 (14)
C5	0.0054 (16)	0.013 (2)	0.028 (2)	0.0004 (15)	0.0016 (15)	−0.0010 (17)
C6	0.0092 (17)	0.013 (2)	0.030 (2)	−0.0021 (17)	0.0029 (15)	−0.0012 (19)
O3	0.0127 (13)	0.0239 (18)	0.0265 (16)	−0.0038 (13)	0.0048 (11)	0.0004 (14)
C3	0.0072 (17)	0.010 (2)	0.031 (2)	0.0029 (16)	0.0021 (15)	−0.0011 (18)
C4	0.0070 (17)	0.0063 (18)	0.029 (2)	0.0008 (16)	0.0033 (15)	−0.0031 (17)
O1	0.0075 (12)	0.0128 (15)	0.0262 (16)	0.0019 (11)	0.0044 (11)	0.0004 (12)
C1	0.0082 (16)	0.017 (2)	0.026 (2)	0.0018 (17)	0.0013 (15)	0.0008 (19)
C2	0.0085 (16)	0.008 (2)	0.024 (2)	0.0031 (16)	0.0011 (14)	0.0010 (16)
O2	0.0072 (12)	0.0112 (15)	0.0304 (17)	−0.0017 (12)	−0.0016 (11)	−0.0012 (13)
C7	0.0082 (17)	0.016 (2)	0.031 (2)	0.0039 (18)	−0.0027 (15)	−0.002 (2)
C8	0.0109 (17)	0.012 (2)	0.027 (2)	−0.0018 (17)	0.0010 (15)	0.0008 (19)
C9	0.0116 (18)	0.015 (2)	0.025 (2)	0.0047 (17)	0.0006 (15)	−0.0034 (18)
C10	0.0088 (17)	0.018 (2)	0.021 (2)	−0.0001 (17)	0.0019 (14)	−0.0033 (18)
C11	0.0094 (17)	0.012 (2)	0.028 (2)	0.0035 (16)	0.0002 (15)	−0.0023 (18)
C12	0.0087 (17)	0.015 (2)	0.028 (2)	−0.0014 (17)	0.0022 (15)	−0.0015 (19)
C13	0.0082 (17)	0.013 (2)	0.029 (2)	0.0031 (16)	0.0003 (15)	−0.0027 (18)
C14	0.0102 (17)	0.016 (2)	0.028 (2)	0.0011 (17)	−0.0003 (15)	−0.0008 (19)
C15	0.0094 (18)	0.020 (2)	0.028 (2)	0.0013 (18)	0.0024 (16)	−0.0025 (19)
C16	0.0106 (18)	0.024 (3)	0.028 (2)	−0.0006 (18)	0.0017 (16)	0.002 (2)
C17	0.0114 (19)	0.027 (3)	0.031 (2)	−0.0001 (19)	0.0006 (17)	−0.001 (2)
C18	0.019 (2)	0.032 (3)	0.032 (3)	−0.005 (2)	−0.0002 (18)	−0.002 (2)

Geometric parameters (Å, º) top

O4—C5	1.414 (5)	C9—C10	1.529 (6)
O4—H4	0.90 (7)	C10—H10A	0.9700
C5—H5	0.9800	C10—H10B	0.9700
C5—C6	1.516 (6)	C10—C11	1.536 (5)
C5—C4	1.537 (6)	C11—H11A	0.9700
C6—H6A	0.9700	C11—H11B	0.9700
C6—H6B	0.9700	C11—C12	1.528 (6)
C6—O3	1.431 (5)	C12—H12A	0.9700
O3—C3	1.449 (5)	C12—H12B	0.9700
C3—H3	0.9800	C12—C13	1.532 (5)
C3—C4	1.514 (6)	C13—H13A	0.9700
C3—C2	1.538 (5)	C13—H13B	0.9700
C4—H4A	0.9800	C13—C14	1.522 (6)
C4—O1	1.447 (4)	C14—H14A	0.9700
O1—C1	1.457 (5)	C14—H14B	0.9700
C1—H1A	0.9700	C14—C15	1.526 (6)
C1—H1B	0.9700	C15—H15A	0.9700
C1—C2	1.519 (6)	C15—H15B	0.9700
C2—H2	0.9800	C15—C16	1.526 (7)
C2—O2	1.425 (5)	C16—H16A	0.9700
O2—C7	1.435 (5)	C16—H16B	0.9700
C7—H7A	0.9700	C16—C17	1.530 (6)
C7—H7B	0.9700	C17—H17A	0.9700
C7—C8	1.510 (6)	C17—H17B	0.9700
C8—H8A	0.9700	C17—C18	1.520 (7)
C8—H8B	0.9700	C18—H18A	0.9600
C8—C9	1.539 (5)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700

C5—O4—H4	107 (4)	C10—C9—H9A	109.0
O4—C5—H5	107.8	C10—C9—H9B	109.0
O4—C5—C6	116.2 (4)	C9—C10—H10A	109.2
O4—C5—C4	115.2 (3)	C9—C10—H10B	109.2
C6—C5—H5	107.8	C9—C10—C11	112.3 (3)
C6—C5—C4	101.5 (3)	H10A—C10—H10B	107.9
C4—C5—H5	107.8	C11—C10—H10A	109.2
C5—C6—H6A	110.9	C11—C10—H10B	109.2
C5—C6—H6B	110.9	C10—C11—H11A	109.0
H6A—C6—H6B	108.9	C10—C11—H11B	109.0
O3—C6—C5	104.4 (4)	H11A—C11—H11B	107.8
O3—C6—H6A	110.9	C12—C11—C10	113.0 (3)
O3—C6—H6B	110.9	C12—C11—H11A	109.0
C6—O3—C3	108.6 (3)	C12—C11—H11B	109.0
O3—C3—H3	111.3	C11—C12—H12A	109.0
O3—C3—C4	107.1 (3)	C11—C12—H12B	109.0
O3—C3—C2	110.7 (3)	C11—C12—C13	113.1 (3)
C4—C3—H3	111.3	H12A—C12—H12B	107.8
C4—C3—C2	105.0 (3)	C13—C12—H12A	109.0
C2—C3—H3	111.3	C13—C12—H12B	109.0
C5—C4—H4A	111.7	C12—C13—H13A	108.9
C3—C4—C5	103.4 (3)	C12—C13—H13B	108.9
C3—C4—H4A	111.7	H13A—C13—H13B	107.7
O1—C4—C5	110.9 (3)	C14—C13—C12	113.4 (3)
O1—C4—C3	107.0 (3)	C14—C13—H13A	108.9
O1—C4—H4A	111.7	C14—C13—H13B	108.9
C4—O1—C1	109.2 (3)	C13—C14—H14A	109.0
O1—C1—H1A	110.7	C13—C14—H14B	109.0
O1—C1—H1B	110.7	C13—C14—C15	113.1 (4)
O1—C1—C2	105.4 (3)	H14A—C14—H14B	107.8
H1A—C1—H1B	108.8	C15—C14—H14A	109.0
C2—C1—H1A	110.7	C15—C14—H14B	109.0
C2—C1—H1B	110.7	C14—C15—H15A	108.8
C3—C2—H2	111.4	C14—C15—H15B	108.8
C1—C2—C3	101.9 (3)	H15A—C15—H15B	107.7
C1—C2—H2	111.4	C16—C15—C14	113.7 (4)
O2—C2—C3	106.2 (3)	C16—C15—H15A	108.8
O2—C2—C1	114.0 (3)	C16—C15—H15B	108.8
O2—C2—H2	111.4	C15—C16—H16A	108.8
C2—O2—C7	112.7 (3)	C15—C16—H16B	108.8
O2—C7—H7A	109.9	C15—C16—C17	113.6 (4)
O2—C7—H7B	109.9	H16A—C16—H16B	107.7
O2—C7—C8	109.2 (3)	C17—C16—H16A	108.8
H7A—C7—H7B	108.3	C17—C16—H16B	108.8
C8—C7—H7A	109.9	C16—C17—H17A	108.9
C8—C7—H7B	109.9	C16—C17—H17B	108.9
C7—C8—H8A	109.4	H17A—C17—H17B	107.7
C7—C8—H8B	109.4	C18—C17—C16	113.5 (4)
C7—C8—C9	111.2 (3)	C18—C17—H17A	108.9
H8A—C8—H8B	108.0	C18—C17—H17B	108.9
C9—C8—H8A	109.4	C17—C18—H18A	109.5
C9—C8—H8B	109.4	C17—C18—H18B	109.5
C8—C9—H9A	109.0	C17—C18—H18C	109.5
C8—C9—H9B	109.0	H18A—C18—H18B	109.5
H9A—C9—H9B	107.8	H18A—C18—H18C	109.5
C10—C9—C8	112.9 (3)	H18B—C18—H18C	109.5

O4—C5—C6—O3	164.6 (3)	C4—O1—C1—C2	−25.6 (4)
O4—C5—C4—C3	−158.5 (3)	O1—C1—C2—C3	33.7 (4)
O4—C5—C4—O1	−44.1 (5)	O1—C1—C2—O2	−80.2 (4)
C5—C6—O3—C3	−31.0 (4)	C1—C2—O2—C7	−77.0 (4)
C5—C4—O1—C1	−105.9 (4)	C2—C3—C4—C5	132.5 (3)
C6—C5—C4—C3	−32.1 (4)	C2—C3—C4—O1	15.4 (4)
C6—C5—C4—O1	82.3 (4)	C2—O2—C7—C8	−172.5 (3)
C6—O3—C3—C4	10.0 (4)	O2—C7—C8—C9	179.4 (3)
C6—O3—C3—C2	−103.9 (4)	C7—C8—C9—C10	−179.1 (4)
O3—C3—C4—C5	14.7 (4)	C8—C9—C10—C11	−175.0 (3)
O3—C3—C4—O1	−102.4 (3)	C9—C10—C11—C12	178.0 (4)
O3—C3—C2—C1	85.6 (4)	C10—C11—C12—C13	178.2 (3)
O3—C3—C2—O2	−154.8 (3)	C11—C12—C13—C14	179.2 (4)
C3—C4—O1—C1	6.2 (4)	C12—C13—C14—C15	179.9 (4)
C3—C2—O2—C7	171.6 (3)	C13—C14—C15—C16	179.6 (4)
C4—C5—C6—O3	38.9 (4)	C14—C15—C16—C17	178.3 (4)
C4—C3—C2—C1	−29.7 (4)	C15—C16—C17—C18	177.3 (4)
C4—C3—C2—O2	89.9 (4)

6-(Tetradecyloxy)hexahydrofuro[3,2-b]furan-3-ol (iso-c14) top

Crystal data top

C₂₀H₃₈O₄	F(000) = 380
M_r = 342.50	D_x = 1.163 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.040 (6) Å	Cell parameters from 1866 reflections
b = 5.438 (5) Å	θ = 2.4–23.7°
c = 25.56 (2) Å	µ = 0.08 mm⁻¹
β = 91.914 (9)°	T = 100 K
V = 978.2 (14) Å³	Plate, colourless
Z = 2	0.3 × 0.1 × 0.02 mm

Data collection top

Bruker APEXII CCD diffractometer	2949 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	R_int = 0.069
φ and ω scans	θ_max = 27.1°, θ_min = 2.4°
Absorption correction: numerical (SADABS; Bruker, 2016)	h = −9→9
T_min = 0.543, T_max = 0.746	k = −6→6
12041 measured reflections	l = −32→32
4278 independent reflections

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)] = 0.055	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.140	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.22 e Å⁻³
4278 reflections	Δρ_min = −0.23 e Å⁻³
221 parameters	Absolute structure: Flack x determined using 980 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −1.2 (10)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	−0.2928 (3)	−0.4743 (5)	0.52486 (10)	0.0275 (6)
H4	−0.194 (6)	−0.559 (8)	0.5245 (16)	0.041*
O3	−0.3534 (3)	−0.4511 (5)	0.38374 (9)	0.0296 (6)
C6	−0.3661 (5)	−0.5840 (7)	0.43214 (14)	0.0264 (8)
H6A	−0.266785	−0.712630	0.435169	0.032*
H6B	−0.492403	−0.661957	0.434930	0.032*
C5	−0.3353 (5)	−0.3874 (7)	0.47378 (13)	0.0249 (8)
H5	−0.453999	−0.286998	0.474978	0.030*
C4	−0.1807 (5)	−0.2270 (7)	0.45005 (13)	0.0233 (8)
H4A	−0.186530	−0.052784	0.462419	0.028*
O1	0.0060 (3)	−0.3353 (5)	0.45978 (9)	0.0251 (6)
C1	0.0720 (5)	−0.4407 (7)	0.41133 (13)	0.0261 (8)
H1A	0.042202	−0.618421	0.409508	0.031*
H1B	0.211101	−0.419197	0.408917	0.031*
C2	−0.0320 (5)	−0.3032 (7)	0.36763 (14)	0.0247 (9)
H2	−0.047190	−0.406857	0.335457	0.030*
C3	−0.2239 (5)	−0.2490 (7)	0.39142 (14)	0.0246 (8)
H3	−0.279669	−0.092979	0.377018	0.029*
O2	0.0514 (3)	−0.0703 (5)	0.35619 (10)	0.0267 (6)
C7	0.2197 (5)	−0.0927 (8)	0.32631 (15)	0.0286 (9)
H7A	0.192742	−0.195626	0.294985	0.034*
H7B	0.321577	−0.173310	0.347733	0.034*
C8	0.2838 (5)	0.1587 (7)	0.30984 (15)	0.0264 (8)
H8A	0.310314	0.260127	0.341405	0.032*
H8B	0.180094	0.239026	0.289060	0.032*
C9	0.4616 (5)	0.1482 (7)	0.27738 (15)	0.0274 (8)
H9A	0.565128	0.069171	0.298453	0.033*
H9B	0.435108	0.043818	0.246248	0.033*
C10	0.5289 (5)	0.3998 (7)	0.25933 (14)	0.0254 (8)
H10A	0.543981	0.509412	0.290107	0.031*
H10B	0.430641	0.472216	0.235393	0.031*
C11	0.7171 (5)	0.3883 (7)	0.23132 (15)	0.0274 (8)
H11A	0.813774	0.309314	0.254778	0.033*
H11B	0.700338	0.283559	0.199816	0.033*
C12	0.7903 (5)	0.6391 (8)	0.21489 (15)	0.0269 (8)
H12A	0.810126	0.742408	0.246494	0.032*
H12B	0.692301	0.719783	0.192145	0.032*
C13	0.9754 (5)	0.6271 (7)	0.18580 (15)	0.0285 (9)
H13A	0.955627	0.523019	0.154311	0.034*
H13B	1.073413	0.546723	0.208622	0.034*
C14	1.0495 (5)	0.8774 (7)	0.16902 (15)	0.0277 (9)
H14A	0.949790	0.960044	0.147198	0.033*
H14B	1.073387	0.979425	0.200626	0.033*
C15	1.2308 (5)	0.8655 (7)	0.13841 (15)	0.0277 (9)
H15A	1.206746	0.763969	0.106733	0.033*
H15B	1.330330	0.782022	0.160177	0.033*
C16	1.3060 (5)	1.1164 (7)	0.12173 (15)	0.0275 (9)
H16A	1.208134	1.197719	0.099038	0.033*
H16B	1.326405	1.219760	0.153298	0.033*
C17	1.4905 (5)	1.1042 (7)	0.09257 (14)	0.0265 (9)
H17A	1.469484	1.002373	0.060793	0.032*
H17B	1.587719	1.020765	0.115103	0.032*
C18	1.5675 (5)	1.3533 (7)	0.07642 (15)	0.0280 (9)
H18A	1.592548	1.453521	0.108237	0.034*
H18B	1.469066	1.439061	0.054693	0.034*
C19	1.7495 (5)	1.3374 (7)	0.04580 (15)	0.0296 (9)
H19A	1.846150	1.245600	0.066956	0.036*
H19B	1.722972	1.242708	0.013287	0.036*
C20	1.8309 (5)	1.5850 (8)	0.03147 (15)	0.0339 (10)
H20A	1.736940	1.676491	0.010062	0.051*
H20B	1.946100	1.560924	0.011619	0.051*
H20C	1.862245	1.677821	0.063460	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0230 (12)	0.0320 (16)	0.0280 (14)	0.0053 (12)	0.0071 (11)	0.0039 (12)
O3	0.0286 (13)	0.0301 (15)	0.0303 (14)	−0.0067 (12)	0.0027 (11)	0.0013 (12)
C6	0.0262 (18)	0.024 (2)	0.030 (2)	−0.0015 (16)	0.0044 (15)	0.0053 (17)
C5	0.0200 (17)	0.027 (2)	0.028 (2)	0.0023 (15)	0.0039 (14)	0.0032 (17)
C4	0.0237 (18)	0.0194 (18)	0.027 (2)	0.0050 (16)	0.0022 (14)	0.0019 (16)
O1	0.0198 (12)	0.0271 (15)	0.0288 (14)	0.0010 (11)	0.0045 (10)	0.0001 (11)
C1	0.0271 (18)	0.025 (2)	0.0265 (19)	−0.0015 (16)	0.0041 (15)	−0.0032 (17)
C2	0.0250 (18)	0.022 (2)	0.027 (2)	−0.0034 (16)	0.0041 (15)	0.0006 (16)
C3	0.0255 (19)	0.0197 (19)	0.029 (2)	0.0009 (16)	0.0031 (15)	0.0018 (16)
O2	0.0261 (13)	0.0242 (15)	0.0305 (15)	−0.0023 (11)	0.0102 (11)	0.0011 (12)
C7	0.0239 (18)	0.031 (2)	0.031 (2)	−0.0005 (17)	0.0083 (15)	0.0042 (18)
C8	0.0256 (18)	0.0230 (19)	0.031 (2)	0.0007 (16)	0.0059 (15)	0.0022 (17)
C9	0.0267 (19)	0.027 (2)	0.028 (2)	0.0012 (17)	0.0065 (15)	0.0039 (17)
C10	0.0237 (18)	0.028 (2)	0.025 (2)	−0.0006 (16)	0.0043 (14)	0.0010 (17)
C11	0.0253 (18)	0.028 (2)	0.029 (2)	0.0004 (17)	0.0066 (15)	0.0036 (17)
C12	0.0237 (18)	0.031 (2)	0.027 (2)	0.0004 (16)	0.0051 (15)	0.0013 (17)
C13	0.0236 (18)	0.033 (2)	0.029 (2)	0.0011 (17)	0.0054 (15)	0.0014 (18)
C14	0.0254 (18)	0.028 (2)	0.030 (2)	−0.0018 (17)	0.0048 (15)	−0.0018 (17)
C15	0.0258 (19)	0.026 (2)	0.032 (2)	0.0011 (16)	0.0040 (15)	0.0016 (17)
C16	0.0242 (19)	0.029 (2)	0.030 (2)	−0.0021 (16)	0.0051 (15)	0.0010 (17)
C17	0.0272 (18)	0.023 (2)	0.030 (2)	0.0006 (16)	0.0046 (15)	0.0037 (17)
C18	0.0261 (19)	0.027 (2)	0.031 (2)	−0.0012 (16)	0.0065 (16)	0.0003 (17)
C19	0.026 (2)	0.029 (2)	0.033 (2)	0.0006 (17)	0.0029 (16)	0.0006 (17)
C20	0.030 (2)	0.033 (3)	0.039 (2)	−0.0057 (18)	0.0091 (17)	0.0007 (19)

Geometric parameters (Å, º) top

O4—H4	0.83 (4)	C10—C11	1.528 (5)
O4—C5	1.411 (4)	C11—H11A	0.9900
O3—C6	1.438 (4)	C11—H11B	0.9900
O3—C3	1.438 (4)	C11—C12	1.522 (5)
C6—H6A	0.9900	C12—H12A	0.9900
C6—H6B	0.9900	C12—H12B	0.9900
C6—C5	1.519 (5)	C12—C13	1.523 (5)
C5—H5	1.0000	C13—H13A	0.9900
C5—C4	1.535 (5)	C13—H13B	0.9900
C4—H4A	1.0000	C13—C14	1.524 (5)
C4—O1	1.454 (4)	C14—H14A	0.9900
C4—C3	1.524 (5)	C14—H14B	0.9900
O1—C1	1.455 (4)	C14—C15	1.521 (5)
C1—H1A	0.9900	C15—H15A	0.9900
C1—H1B	0.9900	C15—H15B	0.9900
C1—C2	1.513 (5)	C15—C16	1.529 (5)
C2—H2	1.0000	C16—H16A	0.9900
C2—C3	1.528 (5)	C16—H16B	0.9900
C2—O2	1.430 (4)	C16—C17	1.520 (5)
C3—H3	1.0000	C17—H17A	0.9900
O2—C7	1.437 (4)	C17—H17B	0.9900
C7—H7A	0.9900	C17—C18	1.521 (5)
C7—H7B	0.9900	C18—H18A	0.9900
C7—C8	1.504 (5)	C18—H18B	0.9900
C8—H8A	0.9900	C18—C19	1.526 (5)
C8—H8B	0.9900	C19—H19A	0.9900
C8—C9	1.526 (5)	C19—H19B	0.9900
C9—H9A	0.9900	C19—C20	1.513 (6)
C9—H9B	0.9900	C20—H20A	0.9800
C9—C10	1.525 (5)	C20—H20B	0.9800
C10—H10A	0.9900	C20—H20C	0.9800
C10—H10B	0.9900

C5—O4—H4	109 (3)	C11—C10—H10A	109.0
C3—O3—C6	108.9 (3)	C11—C10—H10B	109.0
O3—C6—H6A	111.0	C10—C11—H11A	108.9
O3—C6—H6B	111.0	C10—C11—H11B	108.9
O3—C6—C5	103.7 (3)	H11A—C11—H11B	107.7
H6A—C6—H6B	109.0	C12—C11—C10	113.5 (3)
C5—C6—H6A	111.0	C12—C11—H11A	108.9
C5—C6—H6B	111.0	C12—C11—H11B	108.9
O4—C5—C6	115.7 (3)	C11—C12—H12A	108.9
O4—C5—H5	107.8	C11—C12—H12B	108.9
O4—C5—C4	115.1 (3)	C11—C12—C13	113.5 (3)
C6—C5—H5	107.8	H12A—C12—H12B	107.7
C6—C5—C4	102.1 (3)	C13—C12—H12A	108.9
C4—C5—H5	107.8	C13—C12—H12B	108.9
C5—C4—H4A	112.1	C12—C13—H13A	108.8
O1—C4—C5	110.5 (3)	C12—C13—H13B	108.8
O1—C4—H4A	112.1	C12—C13—C14	113.9 (3)
O1—C4—C3	106.6 (3)	H13A—C13—H13B	107.7
C3—C4—C5	102.9 (3)	C14—C13—H13A	108.8
C3—C4—H4A	112.1	C14—C13—H13B	108.8
C4—O1—C1	109.1 (3)	C13—C14—H14A	108.7
O1—C1—H1A	110.6	C13—C14—H14B	108.7
O1—C1—H1B	110.6	H14A—C14—H14B	107.6
O1—C1—C2	105.9 (3)	C15—C14—C13	114.1 (3)
H1A—C1—H1B	108.7	C15—C14—H14A	108.7
C2—C1—H1A	110.6	C15—C14—H14B	108.7
C2—C1—H1B	110.6	C14—C15—H15A	108.7
C1—C2—H2	111.4	C14—C15—H15B	108.7
C1—C2—C3	102.4 (3)	C14—C15—C16	114.2 (3)
C3—C2—H2	111.4	H15A—C15—H15B	107.6
O2—C2—C1	113.4 (3)	C16—C15—H15A	108.7
O2—C2—H2	111.4	C16—C15—H15B	108.7
O2—C2—C3	106.6 (3)	C15—C16—H16A	108.7
O3—C3—C4	107.4 (3)	C15—C16—H16B	108.7
O3—C3—C2	111.3 (3)	H16A—C16—H16B	107.6
O3—C3—H3	111.0	C17—C16—C15	114.0 (3)
C4—C3—C2	104.9 (3)	C17—C16—H16A	108.7
C4—C3—H3	111.0	C17—C16—H16B	108.7
C2—C3—H3	111.0	C16—C17—H17A	108.7
C2—O2—C7	112.7 (3)	C16—C17—H17B	108.7
O2—C7—H7A	109.8	C16—C17—C18	114.3 (3)
O2—C7—H7B	109.8	H17A—C17—H17B	107.6
O2—C7—C8	109.4 (3)	C18—C17—H17A	108.7
H7A—C7—H7B	108.2	C18—C17—H17B	108.7
C8—C7—H7A	109.8	C17—C18—H18A	108.8
C8—C7—H7B	109.8	C17—C18—H18B	108.8
C7—C8—H8A	109.2	C17—C18—C19	113.7 (3)
C7—C8—H8B	109.2	H18A—C18—H18B	107.7
C7—C8—C9	112.2 (3)	C19—C18—H18A	108.8
H8A—C8—H8B	107.9	C19—C18—H18B	108.8
C9—C8—H8A	109.2	C18—C19—H19A	108.8
C9—C8—H8B	109.2	C18—C19—H19B	108.8
C8—C9—H9A	108.8	H19A—C19—H19B	107.7
C8—C9—H9B	108.8	C20—C19—C18	113.9 (3)
H9A—C9—H9B	107.7	C20—C19—H19A	108.8
C10—C9—C8	113.6 (3)	C20—C19—H19B	108.8
C10—C9—H9A	108.8	C19—C20—H20A	109.5
C10—C9—H9B	108.8	C19—C20—H20B	109.5
C9—C10—H10A	109.0	C19—C20—H20C	109.5
C9—C10—H10B	109.0	H20A—C20—H20B	109.5
C9—C10—C11	112.8 (3)	H20A—C20—H20C	109.5
H10A—C10—H10B	107.8	H20B—C20—H20C	109.5

O4—C5—C4—O1	44.5 (4)	C2—O2—C7—C8	172.6 (3)
O4—C5—C4—C3	158.0 (3)	C3—O3—C6—C5	31.2 (3)
O3—C6—C5—O4	−164.6 (3)	C3—C4—O1—C1	−4.8 (4)
O3—C6—C5—C4	−38.8 (3)	C3—C2—O2—C7	−171.1 (3)
C6—O3—C3—C4	−10.6 (3)	O2—C2—C3—O3	154.9 (3)
C6—O3—C3—C2	103.7 (3)	O2—C2—C3—C4	−89.3 (3)
C6—C5—C4—O1	−81.7 (3)	O2—C7—C8—C9	−179.4 (3)
C6—C5—C4—C3	31.8 (3)	C7—C8—C9—C10	179.2 (3)
C5—C4—O1—C1	106.3 (3)	C8—C9—C10—C11	174.6 (3)
C5—C4—C3—O3	−14.1 (3)	C9—C10—C11—C12	−177.8 (3)
C5—C4—C3—C2	−132.6 (3)	C10—C11—C12—C13	−178.6 (3)
C4—O1—C1—C2	24.4 (4)	C11—C12—C13—C14	179.8 (3)
O1—C4—C3—O3	102.2 (3)	C12—C13—C14—C15	−178.1 (3)
O1—C4—C3—C2	−16.3 (4)	C13—C14—C15—C16	−179.7 (3)
O1—C1—C2—C3	−33.4 (3)	C14—C15—C16—C17	178.3 (3)
O1—C1—C2—O2	81.0 (3)	C15—C16—C17—C18	−179.3 (3)
C1—C2—C3—O3	−85.9 (3)	C16—C17—C18—C19	−178.3 (3)
C1—C2—C3—C4	30.0 (4)	C17—C18—C19—C20	−177.7 (3)
C1—C2—O2—C7	77.0 (4)

Selected geometry parameters and intermolecular torsion angles (Å, °) top

Compound	3a	3b	3c	3d
	Iso-C₈	Iso-C₁₀	Iso-C₁₂	Iso-C₁₄
C2—C3—O3	111.02 (18)	111.40 (19)	110.8 (3)	111.3 (3)
O1—C4—C5	110.78 (18)	111.05 (19)	110.8 (3)	110.5 (3)
O2—C2	1.422 (3)	1.422 (3)	1.424 (5)	1.430 (4)
Torsion angle O2—C2···C2—O2ⁱ	52.375	53.870	53.646	54.854

Symmetry code: (i) x, y + 1, z.

Hydrogen-bond geometry (Å,°) top

Compound	3a Iso-C₈	3b Iso-C₁₀	3c Iso-C₁₂	3d Iso-C₁₄
O4—H4	0.88 (3)	0.89 (4)	0.90 (7)	0.83 (4)
H4···O1ⁱ	2.00 (3)	1.97 (5)	1.96 (7)	2.03 (4)
O4···O1ⁱ	2.827 (2)	2.823 (3)	2.830 (4)	2.834 (4)
O4—H4···O1ⁱ	155 (3)	160 (4)	162 (5)	161 (4)

Symmetry code: (i) -x, 1/2 + y, 1 - z for 3a and -x, y - 1/2, -z + 1 for 3b, 3c and 3d.

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