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The crystal structure of the inclusion complex of β-cyclodextrin with lipoic acid was determined from laboratory powder diffraction data. Thermogravimetric data was used to estimate the number of water molecules in the crystal structure. Lipoic acid is included in β-cyclodextrin through its primary face with the five-membered ring reaching the center plane of the cyclodextrin cavity and its fatty acid chain adopting a bent conformation. Lipoic acid and β-cyclodextrin form a channel-like packing which is stabilized by guest–host hydrogen bonding and close contacts, host–host intermolecular interactions and hydrogen bonding involving the water molecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112004284/gp5045sup1.cif
Contains datablocks global, LIP

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768112004284/gp5045LIPsup2.rtv
Contains datablock LIP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112004284/gp5045LIPsup3.hkl
Contains datablock LIP

CCDC reference: 879423

Computing details top

Program(s) used to refine structure: GSAS.

(LIP) top
Crystal data top
C42O35·C8O2S2·O9β = 110.5195°
Mr = 700.31V = 6812.18 Å3
Monoclinic, C2Z = 8
a = 18.8929 ÅCu Kα radiation, λ = 1.5405 Å
b = 24.4634 ÅT = 295 K
c = 15.7376 Å?, ? × ? × ? mm
Data collection top
Bruker D8 Advanced
diffractometer
Data collection mode: reflection
Radiation source: CuKα, 2.2kW Cu anode long fine focus ceramic X-ray tubeScan method: step
Ge 111 crystal monochromator2θmin = 2.999°, 2θmax = 49.979°, 2θstep = 0.01°
Specimen mounting: plate holder
Refinement top
Least-squares matrix: full4699 data points
Rp = 0.092Profile function: CW Profile function number 5 with 17 terms Profile function not installed. This is an error & should not happen! Peak tails are ignored where the intensity is below 0.0100 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rwp = 0.128167 parameters
Rexp = 0.033141 restraints
R(F2) = 0.12487(Δ/σ)max = 0.05
χ2 = 30.581Background function: GSAS Background function number 1 with 18 terms. Shifted Chebyshev function of 1st kind 1: 528.134 2: -517.062 3: 167.079 4: -86.8962 5: 62.7871 6: -26.5990 7: 26.6140 8: 16.8098 9: -17.0629 10: -6.71591 11: 23.5081 12: 4.96859 13: 20.7329 14: -1.06822 15: -8.52721 16: -5.28689 17: 14.5610 18: -7.76431
Crystal data top
C42O35·C8O2S2·O9β = 110.5195°
Mr = 700.31V = 6812.18 Å3
Monoclinic, C2Z = 8
a = 18.8929 ÅCu Kα radiation, λ = 1.5405 Å
b = 24.4634 ÅT = 295 K
c = 15.7376 Å?, ? × ? × ? mm
Data collection top
Bruker D8 Advanced
diffractometer
Scan method: step
Specimen mounting: plate holder2θmin = 2.999°, 2θmax = 49.979°, 2θstep = 0.01°
Data collection mode: reflection
Refinement top
Rp = 0.092χ2 = 30.581
Rwp = 0.1284699 data points
Rexp = 0.033167 parameters
R(F2) = 0.12487141 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O411.0686 (4)0.4207 (7)0.7932 (5)0.02219*
C111.1162 (5)0.4148 (9)0.7415 (8)0.02547*
C211.1936 (5)0.4204 (10)0.8165 (9)0.02547*
C311.2103 (6)0.4793 (10)0.8490 (9)0.02547*
C411.2002 (6)0.5166 (10)0.7672 (10)0.02547*
C511.1214 (6)0.5073 (9)0.6951 (9)0.02547*
O211.1964 (5)0.3867 (10)0.8900 (8)0.02219*
O311.2853 (6)0.4828 (10)0.9092 (10)0.02219*
O511.1097 (5)0.4515 (9)0.6703 (9)0.02219*
O611.1787 (4)0.5504 (3)0.594 (3)0.02219*
C611.1111 (4)0.5452 (3)0.6109 (15)0.02547*
O421.2652 (6)0.5404 (4)0.7544 (10)0.02219*
C121.2772 (3)0.5984 (4)0.7604 (9)0.02547*
C221.3087 (4)0.6336 (4)0.8455 (9)0.02547*
C321.2511 (4)0.6762 (4)0.8499 (9)0.02547*
C421.2263 (4)0.7103 (4)0.7626 (9)0.02547*
C521.2003 (4)0.6725 (4)0.6792 (9)0.02547*
O221.3287 (4)0.5999 (4)0.9226 (9)0.02219*
O321.2851 (4)0.7105 (4)0.9246 (9)0.02219*
O521.2540 (3)0.6314 (4)0.6820 (9)0.02219*
O621.1889 (12)0.7606 (2)0.5908 (7)0.02219*
C621.191 (2)0.7034 (2)0.5885 (15)0.02547*
O431.2482 (5)0.7654 (2)0.7594 (6)0.02219*
C131.1854 (4)0.7978 (4)0.7589 (7)0.02547*
C231.1713 (4)0.8257 (4)0.8384 (7)0.02547*
C331.0925 (4)0.8123 (4)0.8390 (7)0.02547*
C431.0341 (4)0.8295 (4)0.7476 (6)0.02547*
C531.0531 (4)0.8013 (4)0.6707 (7)0.02547*
O231.2259 (4)0.8086 (4)0.9203 (7)0.02219*
O331.0808 (4)0.8421 (4)0.9092 (7)0.02219*
O531.1284 (4)0.8118 (4)0.6763 (7)0.02219*
O631.0421 (9)0.8815 (11)0.5793 (10)0.02219*
C631.0097 (5)0.8299 (4)0.5822 (2)0.02547*
O440.9578 (6)0.8104 (6)0.7301 (16)0.02219*
C140.8945 (5)0.8479 (6)0.6994 (12)0.02547*
C240.8610 (5)0.8477 (6)0.7749 (12)0.02547*
C340.8238 (5)0.7931 (6)0.7801 (11)0.02547*
C440.7644 (5)0.7806 (6)0.6868 (10)0.02547*
C540.8032 (5)0.7816 (6)0.6156 (11)0.02547*
O240.9182 (6)0.8587 (6)0.8583 (12)0.02219*
O340.7893 (5)0.7970 (6)0.8459 (11)0.02219*
O540.8400 (5)0.8321 (6)0.6158 (12)0.02219*
O640.6677 (9)0.7788 (11)0.5044 (11)0.02219*
C640.7468 (8)0.7634 (12)0.5206 (11)0.02547*
O450.6856 (3)0.7877 (5)0.6651 (9)0.02219*
C150.6423 (8)0.7392 (5)0.6550 (10)0.02547*
C250.6165 (8)0.7152 (5)0.7289 (10)0.02547*
C350.6507 (8)0.6587 (5)0.7581 (9)0.02547*
C450.6350 (7)0.6216 (5)0.6750 (9)0.02547*
C550.6562 (7)0.6503 (5)0.6001 (10)0.02547*
O250.6377 (9)0.7511 (5)0.8033 (10)0.02219*
O350.6183 (8)0.6359 (5)0.8180 (9)0.02219*
O550.6243 (7)0.7032 (5)0.5806 (10)0.02219*
O650.5818 (13)0.5810 (13)0.486 (2)0.02219*
C650.6431 (9)0.6200 (11)0.5070 (14)0.02547*
O460.6637 (6)0.5669 (3)0.7021 (8)0.02219*
C160.6138 (6)0.5260 (7)0.7117 (11)0.02546*
C260.6559 (6)0.5025 (7)0.8058 (10)0.02547*
C360.7352 (6)0.4841 (8)0.8145 (10)0.02547*
C460.7299 (5)0.4433 (7)0.7386 (10)0.02547*
C560.6834 (5)0.4684 (7)0.6461 (10)0.02547*
O260.6611 (7)0.5424 (8)0.8718 (11)0.02219*
O360.7687 (6)0.4584 (8)0.8989 (10)0.02219*
O560.6120 (6)0.4879 (6)0.6437 (10)0.02219*
O660.73114 (18)0.39733 (15)0.5740 (11)0.02219*
C660.67327 (18)0.43584 (15)0.5595 (10)0.02547*
O470.8060 (5)0.4397 (5)0.7464 (9)0.02219*
C170.8329 (5)0.3858 (7)0.7521 (8)0.02547*
C270.9006 (5)0.3680 (8)0.8400 (8)0.02547*
C370.9727 (5)0.4008 (8)0.8544 (8)0.02547*
C470.9956 (5)0.3947 (8)0.7704 (8)0.02547*
C570.9287 (5)0.4123 (7)0.6859 (8)0.02547*
O270.8773 (5)0.3760 (8)0.9146 (7)0.02219*
O371.0305 (5)0.3800 (8)0.9307 (8)0.02219*
O570.8624 (4)0.3826 (7)0.6781 (8)0.02219*
O670.931 (3)0.3582 (10)0.545 (3)0.02219*
C670.9464 (15)0.4094 (10)0.5953 (12)0.02547*
S11.0081 (12)0.6430 (16)0.7515 (11)0.00991*
S20.9349 (10)0.5824 (14)0.7507 (8)0.00991*
C20.9448 (9)0.6012 (15)0.5852 (10)0.02547*
C10.9731 (13)0.6570 (15)0.6299 (11)0.02547*
C30.8920 (9)0.5731 (13)0.6279 (7)0.02547*
C40.8874 (11)0.5101 (9)0.610 (3)0.02547*
C50.8090 (12)0.4828 (15)0.596 (2)0.02547*
C60.7641 (10)0.4749 (9)0.4936 (14)0.02547*
C70.6938 (14)0.5120 (12)0.4571 (15)0.02547*
C80.672 (2)0.5199 (7)0.3525 (11)0.02547*
O20.6518 (15)0.4829 (9)0.2959 (16)0.02219*
O10.6504 (11)0.5698 (8)0.3332 (14)0.02219*
O900.0560 (7)0.0855 (10)0.0914 (12)0.02219*
O910.4351 (15)0.0833 (14)0.109 (3)0.02219*
O920.0191 (15)0.0793 (10)0.217 (2)0.02219*
O930.489 (3)0.732 (3)0.196 (4)0.02219*
O940.1481 (8)0.3108 (7)0.0406 (14)0.02219*
O950.1696 (15)0.6454 (14)0.121 (4)0.02219*
O960.0626 (5)0.2421 (7)0.0091 (12)0.02219*
O970.2791 (14)0.6415 (12)0.0346 (12)0.02219*
O980.0332 (12)0.2548 (14)0.546 (2)0.02219*

Experimental details

Crystal data
Chemical formulaC42O35·C8O2S2·O9
Mr700.31
Crystal system, space groupMonoclinic, C2
Temperature (K)295
a, b, c (Å)18.8929, 24.4634, 15.7376
β (°) 110.5195
V3)6812.18
Z8
Radiation typeCu Kα, λ = 1.5405 Å
Specimen shape, size (mm)?, ? × ? × ?
Data collection
DiffractometerBruker D8 Advanced
diffractometer
Specimen mountingPlate holder
Data collection modeReflection
Scan methodStep
2θ values (°)2θmin = 2.999 2θmax = 49.979 2θstep = 0.01
Refinement
R factors and goodness of fitRp = 0.092, Rwp = 0.128, Rexp = 0.033, R(F2) = 0.12487, χ2 = 30.581
No. of data points4699
No. of parameters167
No. of restraints141

Computer programs: GSAS.

 

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