Crystal structure of seladelpar, C21H23F3O5S, from synchrotron powder diffraction data and density functional theory

Salazar, J.K.; Kaduk, J.A.; Dosen, A.; Rost, M.; Blanton, T.N.

doi:10.1107/S2056989026007875

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ISSN: 2056-9890

Volume 82| Part 9| September 2026|

https://doi.org/10.1107/S2056989026007875

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Crystal structure of seladelpar, C₂₁H₂₃F₃O₅S, from synchrotron powder diffraction data and density functional theory

Jacob K. Salazar,^a James A. Kaduk,^b,^c ^* Anja Dosen,^d Megan Rost ^d and Thomas N. Blanton ^d

^aNorth Central College, Department of Chemistry, 131 S. Loomis St., Naperville IL 60540, USA, ^bNorth Central College, Department of Physics, 131 S. Loomis St., Naperville IL 60540, USA, ^cIllinois Institute of Technology, Department of Chemistry, 3101 S. Dearborn St., Chicago IL 60616, USA, and ^dICDD, 12 Campus Blvd., Newtown Square PA 19073-3273, USA
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 27 May 2026; accepted 30 July 2026; online 4 August 2026)

The crystal structure of seladelpar, C₂₁H₂₃F₃O₅S [systematic name 2-(4-{(2R)-2-ethoxy-3-[4-(trifluoromethyl)phenoxy]propylsulfanyl}-2-methylphenoxy)acetic acid], has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional theory techniques. Seladelpar crystallizes in space group P2₁2₁2₁ and the molecule adopts a U-shaped conformation. The crystal structure is characterized by layers lying parallel to the ab plane. One classical O—H⋯O hydrogen bond links the carboxylic acid group and an ether O into chains propagating along the b-axis direction and the chains are consolidated by a weak C—H⋯S hydrogen bond.

Keywords: powder diffraction; seladelpar; Livdelzi; Rietveld refinement; density functional theory.

CCDC references: 2577790; 2577791

1. Chemical context

Seladelpar, C₂₁H₂₃F₃O₅S (marketed as Livdelzi, as the lysine dihydrate salt), is used to treat primary biliary cholangitis, an autoimmune disease of the liver (Shukla & Misra, 2025 ). The systematic name (CAS Registry Number 851528-79-5) is 2-[4-[(2R)-2-ethoxy-3-[4-(trifluoromethyl)phenoxy]propyl]sulfanyl-2-methylphenoxy]acetic acid.

This work was carried out as part of a project (Kaduk et al., 2014 ) to determine the crystal structures of large-volume commercial pharmaceuticals, and include high-quality powder diffraction data for them in the Powder Diffraction File (Kabekkodu et al., 2024 ).

2. Structural commentary

The molecular structure of seladelpar is illustrated in Fig. 1. The root-mean-square difference of the non-H atoms in the Rietveld-refined and VASP-optimized structures, calculated using the Mercury (Macrae et al., 2020 ) CSD-Materials/search/crystal packing similarity tool is 0.139 Å (Fig. 2); the structures are essentially identical. The root-mean-square Cartesian displacement of the non-H atoms in the refined and optimized structures, calculated using the Mercury Calculate/molecule overlay tool, is 0.112 Å (Fig. 3). The agreements are within the normal range for correct structures (van de Streek & Neumann, 2014 ). Given the normal representation of the molecule in an extended conformation, the bent solid-state conformation with the phenyl rings approximately parallel may be unexpected. The remaining discussion will emphasize the VASP-optimized structure.

Figure 1
The molecular structure of seladelpar, based on the Rietveld refinement, with the atom numbering. The atoms are represented by 50% probability spheroids.

Figure 2
Comparison of the Rietveld-refined (colored by atom type) and VASP-optimized (pale green) structures of seladelpar, calculated using the Mercury CSD-Materials/Search/Crystal Packing Similarity tool. The root-mean-square Cartesian displacement is 0.139 Å.

Figure 3
Comparison of the refined structure of seladelpar (red) to the VASP-optimized structure (blue). The comparison was generated using the Mercury Calculate/Molecule Overlay tool; the r.m.s. difference is 0.112 Å.

Almost all of the bond distances, bond angles, and torsion angles fall within the normal ranges indicated by a Mercury Mogul geometry check (Macrae et al., 2020). Only the torsion angles involving rotation about the S1—C13 bond are flagged as unusual. They lie in broad valleys of bimodal 0/180° distributions of similar torsion angles, so the conformation of the molecule is slightly unusual, but not unprecedented. The mean plane of the aromatic ring with the trifluoromethyl substituent corresponds approximately with the (1 $[\overline{1}]$ 2) Miller plane, and the mean plane of the other phenyl ring is approximately (11 $[\overline{1}]$ ). The bent shape of the molecule is reflected in the normal S1—C11—C10—C12 (gauche) and O5—C10—C11—S1(trans) torsion angles (Table 1).

Table 1
Selected torsion angles (°)

C13—S1—C11—C10	−89.2	C11—C10—O5—C14	75.6
S1—C11—C10—C12	60.4	C10—O5—C14—C21	162.4
O5—C10—C11—S1	−177.7	C10—C12—O6—C15	−169.8
C17—C13—S1—C11	125.4	O5—C10—C12—O6	−64.9
C18—C13—S1—C11	−58.4	C19—O7—C29—C30	−82.2
C11—C10—C12—O6	58.8

Quantum chemical geometry optimization of the isolated seladelpar molecule (DFT/B3LYP/6-31G*/water) using Spartan '24 (Wavefunction, 2025 ) indicated that the observed conformation is 3.6 kcal mol⁻¹ higher in energy than a local minimum, which has a similar overall shape (r.m.s. difference = 0.56 Å) but differences at the periphery of the molecule. The global minimum-energy conformation (MMFF force field) is 8.3 kcal mol⁻¹ lower in energy, with a similar overall shape (r.m.s. difference = 1.76 Å) but with differences in the orientations of the carboxylic acid and trifluoromethyl groups. The conformation of seladelpar in the PDB entry 8HUP is very different from that observed here (Fig. 4; r.m.s. difference = 2.80 Å) and 1.4 kcal mol⁻¹ lower in energy. Apparently, the molecule is flexible, and intermolecular interactions are important in determining the observed conformation.

Figure 4
Comparison of the molecular structure of seladelpar determined here (orange) with that in PDB entry 8HUP (green). The root-mean-square difference is 2.801 Å.

3. Supramolecular features

The crystal structure (Fig. 5) is characterized by layers lying parallel to the ab plane. Parallel stacking of rings is apparent when viewed in different directions. The Mercury aromatics analyser indicates two strong (d = 5.09 Å) interactions between phenyl rings, three moderate (d = 5.89, 5.89, and 6.32 Å), and some weaker interactions (d > 8.7 Å). Analysis of the contributions to the total crystal energy of the structure using the Forcite module of Materials Studio (Dassault Systèmes, 2025 ) indicated that the intramolecular energy is dominated by angle distortion terms, and that bond and torsion terms are also significant. The intermolecular energy is dominated by van der Waals attractions, which in this force field-based analysis include hydrogen bonds. The hydrogen bonds are better discussed using the results of the DFT calculation.

Figure 5
Crystal structure of seladelpar, viewed down the a-axis direction.

There is one classical O—H⋯O hydrogen bond in the structure (Table 2). The energy of this bond (14.7 kcal mol⁻¹) was calculated using the correlation of Rammohan & Kaduk (2018 ). This links the carboxylic acid and the ether O5 atom into chains propagating along the b-axis direction, with graph-set motif (Etter, 1990 ; Bernstein et al., 1995 ; Motherwell et al., 2000 ) C(13). A less-traditional (and from the overlap population, surprisingly strong) C—H⋯S hydrogen bond links an aromatic ring and the S atom, and reinforces the chains along the b-axis.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H1⋯O5ⁱ	1.01	1.72	2.725	175
C23—H16⋯S1ⁱⁱ	1.09	2.72	3.785	166
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

The volume enclosed by the Hirshfeld surface of seladelpar (Fig. 6; Hirshfeld, 1977 ; Spackman et al., 2021 ) is 546.7 Å³ or 98.6% of 1/4 of the unit cell volume. The packing density is thus typical. The close contacts (red in Fig. 6) involve the hydrogen bonds. The volume per non-hydrogen atom is normal, at 18.5 Å³.

Figure 6
The Hirshfeld surface of seladelpar. Intermolecular contacts longer than the sums of the van der Waals radii are colored blue, and contacts shorter than the sums of the radii are colored red. Contacts approximately equal to the sums of radii are white.

The Bravais–Friedel–Donnay–Harker (Bravais, 1866 ; Friedel, 1907 ; Donnay & Harker, 1937 ) algorithm suggests that we might expect lozenge morphology for seladelpar, with {001} as the major faces. A second-order spherical harmonic model for preferred orientation was included. The texture index was 1.006, indicating that the preferred orientation was negligible in this rotated capillary specimen.

4. Database survey

Powder diffraction data for anhydrous and dihydrate lysine salts of seladelpar are reported in US Patent US 7,709,682 B2 (Abdel-Magid et al., 2010 ; Janssen Pharmaceutical). We are unaware of any published powder diffraction data for seladelpar itself. The structures of several proteins complexed with seladelpar, have been determined (Kamata et al., 2023 ; PDB entries 8HUN, 8HUO, and 8HUP). A reduced cell search in the Cambridge Structural Database (Groom et al., 2016 ), with the chemistry C, H, F, O and S only, yielded no hits.

5. Synthesis and crystallization

Seladelpar is a commercial reagent, purchased from TargetMol (Batch #225397), and was used as-received.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The white powder was packed into a 1.5 mm diameter Kapton capillary, and rotated during the measurement at 50 Hz. The powder pattern was measured at 295 K at beam line 11-BM (Lee et al., 2008 ; Wang et al., 2008 ; Antao et al., 2008 ) of the Advanced Photon Source at Argonne National Laboratory using a wavelength of 0.4687342 Å from 0.5–50° 2θ with a step size of 0.001° and a counting time of 0.1 sec step⁻¹. The high-resolution powder diffraction data were collected using twelve silicon crystal analyzers that allow for high angular resolution, high precision, and accurate peak positions. A mixture of silicon (NIST SRM 640c) and alumina (NIST SRM 676a) standards (ratio Al₂O₃:Si = 2:1 by weight) was used to calibrate the instrument and refine the monochromatic wavelength used in the experiment.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₁H₂₃F₃O₅S
M_r	444.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	8.85689 (7), 10.62563 (8), 23.57851 (14)
V (Å³)	2218.98 (2)
Z	4
Radiation type	Synchrotron, λ = 0.46873 Å
μ (mm⁻¹)	0.02
Specimen shape, size (mm)	Cylinder, 2.0 × 1.5

Data collection
Diffractometer	11-BM, APS
Specimen mounting	Kapton capillary
Data collection mode	Transmission
Scan method	Step
2θ values (°)	2θ_min = 0.510, 2θ_max = 49.995, 2θ_step = 0.001

Refinement
R factors and goodness of fit	R_p = 0.066, R_wp = 0.088, R_exp = 0.027, R(F²) = 0.06486, χ² = 11.169
No. of parameters	114
No. of restraints	75
(Δ/σ)_max	11.051
Computer programs: GSAS-II (Toby & Von Dreele, 2013).

The pattern was indexed on a primitive orthorhombic unit cell with a = 8.87586, b = 10.62254, c = 23.54278 Å, V = 2219.7 Å³, and Z = 4 using N-TREOR as incorporated into EXPO2014 (Altomare et al., 2013 ). The suggested space group was P2₁2₁2₁, which was confirmed by the successful solution and refinement of the structure. This cell does not account for a few weak peaks, so the sample contains at least one crystalline impurity.

The molecular structure of seladelpar was downloaded from PubChem (Kim et al., 2023 ) as Conformer3D_COMPOUND_CID_11236126.sdf. It was converted to a *.mol2 file using Mercury (Macrae et al., 2020), and to a Fenske–Hall Z-matrix using OpenBabel (O'Boyle et al., 2011 ). The structure was solved using parallel tempering techniques as implemented in FOX (Favre-Nicolin & Černý, 2002 ).

Rietveld refinement was carried out using GSAS-II (Toby & Von Dreele, 2013 ). Only the 1.5–19.0° portion of the pattern was included in the refinements (d_min = 1.420 Å). All non-H bond distances and angles were subjected to restraints, based on a Mercury/Mogul Geometry Check (Sykes et al., 2011 ; Bruno et al., 2004 ). The Mogul average and standard deviation for each quantity were used as the restraint parameters. The aromatic rings were restrained to be planar. The restraints contributed 7.3% to the overall χ². The hydrogen atoms were included in calculated positions, which were recalculated during the refinement using Mercury. The U_iso values of the non-H atoms were grouped by chemical similarity. The U_iso of the H atoms were fixed at 1.2× the U_iso of the heavy atom to which they are attached. The peak profiles were described using the generalized microstrain model (Stephens, 1999 ). The background was modeled using a six-term shifted Chebyshev polynomial, with a peak at 6.08° to model the scattering from the Kapton capillary and any amorphous component of the sample.

The final refinement of 114 variables using 17,501 observations and 75 restraints yielded the residuals R_wp = 0.0914 and GOF = 3.34. The largest peak (1.21 Å from F4) and hole (1.95 Å from S1) in the difference-Fourier map are 0.23 (4) and −0.20 (4) e Å⁻³, respectively. The final Rietveld plot is shown in Fig. 7. The largest features in the normalized error plot are at the impurity peaks and in the shape of the lowest-angle 002 peak.

Figure 7
The Rietveld plot for seladelpar. The blue crosses represent the observed data points, and the green line is the calculated pattern. The cyan curve is the normalized error plot, and the red line is the background curve. The blue tick marks indicate the peak positions. The vertical scale has been multiplied by a factor of 20× for 2θ > 9.0°.

The crystal structure of seladelpar was optimized (fixed experimental unit cell) with density functional theory techniques using VASP (Kresse & Furthmüller, 1996 ) through the MedeA graphical interface (Materials Design, 2024 ). The calculation was carried out on 32 cores of a 144-core (768 Gb memory) HPE Superdome Flex 280 Linux server at North Central College. The calculation used the GGA-PBE functional, a plane wave cutoff energy of 400.0 eV, and a k-point spacing of 0.5 Å⁻¹ leading to a 2 × 2 × 1 mesh, and took ∼11.9 h. Single-point density functional theory calculations (fixed experimental cell) and population analysis were carried out using CRYSTAL23 (Erba et al., 2023 ). (fixed experimental cell) and population analysis were carried out using CRYSTAL17 (Dovesi et al., 2018 ). The basis sets for the H, C, and O atoms in the calculation were those of Gatti et al. (1994 ), and those for F and S were from Peintinger et al. (2013 ). The calculations were run on a 3.5 GHz PC using 8 k-points and the B3LYP functional, and took ∼3.2 h. The powder pattern has been submitted to ICDD for inclusion in the Powder Diffraction File (PDF).

Supporting information

CCDC references: 2577790; 2577791

Crystal structure: contains datablocks seladelpar, seladelpar_VASP. DOI: https://doi.org/10.1107/S2056989026007875/hb8227sup1.cif

checkCIF report

Computing details top

2-(4-{(2R)-2-Ethoxy-3-[4-(trifluoromethyl)phenoxy]propylsulfanyl}-2-methylphenoxy)acetic acid (seladelpar) top

Crystal data top

C₂₁H₂₃F₃O₅S	Z = 4
M_r = 444.46	D_x = 1.330 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Synchrotron radiation, λ = 0.46873 Å
a = 8.85689 (7) Å	µ = 0.02 mm⁻¹
b = 10.62563 (8) Å	T = 295 K
c = 23.57851 (14) Å	cylinder, 2.0 × 1.5 mm
V = 2218.98 (2) Å³

Data collection top

11-BM, APS diffractometer	Scan method: step
Specimen mounting: Kapton capillary	2θ_min = 0.510°, 2θ_max = 49.995°, 2θ_step = 0.001°
Data collection mode: transmission

Refinement top

Least-squares matrix: full	114 parameters
R_p = 0.066	75 restraints
R_wp = 0.088	25 constraints
R_exp = 0.027	Weighting scheme based on measured s.u.'s
R(F²) = 0.06486	(Δ/σ)_max = 11.051
49486 data points	Background function: Background function: "chebyschev-1" function with 6 terms: 83.2(15), 38.6(18), 1.6(7), -42.6(15), 20.8(9), 3.7(4), Background peak parameters: pos, int, sig, gam: 6.080(24), 7.1(3)e4, 3.46(12)e4, 0.100,
Profile function: Finger-Cox-Jephcoat function parameters U, V, W, X, Y, SH/L: peak variance(Gauss) = Utan(Th)²+Vtan(Th)+W: peak HW(Lorentz) = X/cos(Th)+Ytan(Th); SH/L = S/L+H/L U, V, W in (centideg)², X & Y in centideg 1.163, -0.126, 0.063, 0.000, 0.000, 0.002,	Preferred orientation correction: Simple spherical harmonic correction Order = 2 Coefficients: 0:0:C(2,0) = -0.1570; 0:0:C(2,2) = 0.0680

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

	x	y	z	U_iso*/U_eq
S1	−0.0693 (5)	0.8031 (4)	0.2987 (2)	0.090 (2)*
F2	0.7564 (9)	0.5457 (7)	0.0969 (4)	0.110 (2)*
F3	0.7032 (8)	0.7385 (6)	0.0780 (3)	0.110 (2)*
F4	0.5772 (9)	0.5866 (7)	0.0556 (3)	0.110 (2)*
O5	0.2116 (8)	0.6317 (8)	0.4072 (4)	0.074 (2)*
O6	0.3274 (10)	0.6649 (8)	0.2992 (4)	0.074 (2)*
O7	0.3205 (9)	0.9186 (8)	0.0999 (3)	0.091 (2)*
O8	0.4964 (8)	1.2284 (8)	0.0955 (5)	0.091 (2)*
O9	0.2451 (9)	1.1752 (7)	0.0908 (5)	0.091 (2)*
C10	0.1126 (10)	0.6346 (9)	0.3592 (4)	0.074 (2)*
C11	0.0640 (11)	0.7684 (10)	0.3557 (4)	0.074 (2)*
C12	0.1936 (12)	0.5916 (10)	0.3060 (4)	0.074 (2)*
C13	0.0490 (9)	0.8496 (9)	0.2404 (3)	0.038 (3)*
C14	0.1323 (11)	0.6125 (11)	0.4623 (5)	0.074 (2)*
C15	0.4075 (14)	0.6504 (12)	0.2525 (4)	0.110 (2)*
C16	0.1267 (10)	0.8081 (8)	0.1427 (3)	0.038 (3)*
C17	0.0330 (9)	0.7833 (8)	0.1890 (4)	0.038 (3)*
C18	0.1583 (11)	0.9472 (8)	0.2440 (3)	0.038 (3)*
C19	0.2459 (13)	0.8937 (11)	0.1496 (3)	0.038 (3)*
C20	0.2492 (11)	0.9734 (9)	0.1961 (4)	0.038 (3)*
C21	0.2342 (15)	0.5533 (13)	0.4997 (5)	0.074 (2)*
C22	0.5226 (13)	0.7313 (10)	0.2432 (4)	0.110 (2)*
C23	0.3515 (14)	0.5777 (12)	0.2093 (4)	0.110 (2)*
C24	0.5616 (11)	0.6439 (11)	0.1505 (4)	0.110 (2)*
C25	0.1227 (10)	0.7196 (8)	0.0935 (4)	0.038 (3)*
C26	0.5977 (12)	0.7303 (11)	0.1910 (4)	0.110 (2)*
C27	0.4405 (10)	0.5645 (11)	0.1606 (3)	0.110 (2)*
C28	0.6537 (8)	0.6326 (6)	0.0973 (3)	0.110 (2)*
C29	0.4303 (10)	1.0128 (8)	0.0970 (5)	0.091 (2)*
C30	0.3809 (9)	1.1448 (7)	0.0919 (8)	0.091 (2)*
H1	0.59404	1.18258	0.09406	0.1095*
H2	0.01509	0.57462	0.36702	0.0882*
H3	0.16412	0.82616	0.34929	0.0882*
H4	0.01101	0.79351	0.39581	0.0882*
H5	0.22332	0.49253	0.30988	0.0882*
H6	0.12036	0.60460	0.26937	0.0882*
H7	0.09737	0.70291	0.47965	0.0882*
H8	0.03346	0.55313	0.45607	0.0882*
H9	−0.05405	0.71139	0.18531	0.0453*
H10	0.17186	1.00095	0.28299	0.0453*
H11	0.32173	1.05616	0.19577	0.0453*
H12	0.33292	0.61300	0.50555	0.0882*
H13	0.26901	0.46322	0.48197	0.0882*
H14	0.17938	0.53796	0.54046	0.0882*
H15	0.55678	0.79704	0.27622	0.1322*
H16	0.24187	0.53194	0.21275	0.1322*
H17	0.02154	0.66162	0.09621	0.0453*
H18	0.22226	0.65950	0.09449	0.0453*
H19	0.12138	0.77315	0.05412	0.0453*
H20	0.68590	0.79927	0.18265	0.1322*
H21	0.41411	0.49062	0.13016	0.1322*
H22	0.49806	1.00599	0.13542	0.1095*
H23	0.50063	0.99235	0.06025	0.1095*

Geometric parameters (Å, º) top

S1—C11	1.826 (6)	C21—C14	1.410 (14)
S1—C13	1.798 (5)	C21—H12	1.089 (13)
F2—F3	2.149 (9)	C21—H13	1.088 (13)
F2—F4	1.912 (9)	C21—H14	1.090 (13)
F2—C28	1.296 (8)	C22—C15	1.352 (6)
F3—F2	2.149 (9)	C22—C26	1.399 (6)
F3—F4	2.032 (9)	C22—H15	1.089 (6)
F3—C28	1.291 (8)	C23—C15	1.371 (7)
F4—F2	1.912 (9)	C23—C27	1.399 (7)
F4—F3	2.032 (9)	C23—H16	1.089 (8)
F4—C28	1.290 (8)	C24—C26	1.362 (5)
O5—C10	1.431 (7)	C24—C27	1.385 (5)
O5—C14	1.491 (9)	C24—C28	1.502 (5)
O6—C12	1.428 (8)	C25—C16	1.494 (6)
O6—C15	1.319 (6)	C25—H17	1.089 (9)
O7—C19	1.370 (6)	C25—H18	1.089 (9)
O7—C29	1.397 (6)	C25—H19	1.089 (10)
O8—C30	1.357 (7)	C26—C22	1.399 (6)
O8—H1	0.993 (7)	C26—C24	1.362 (5)
O9—C30	1.246 (8)	C26—H20	1.089 (7)
C10—O5	1.431 (7)	C27—C23	1.399 (7)
C10—C11	1.488 (7)	C27—C24	1.385 (5)
C10—C12	1.516 (8)	C27—H21	1.090 (7)
C10—H2	1.089 (9)	C28—F2	1.296 (8)
C11—S1	1.826 (6)	C28—F3	1.291 (8)
C11—C10	1.488 (7)	C28—F4	1.290 (8)
C11—H3	1.089 (11)	C28—C24	1.502 (5)
C11—H4	1.088 (10)	C29—O7	1.397 (6)
C12—O6	1.428 (8)	C29—C30	1.474 (7)
C12—C10	1.516 (8)	C29—H22	1.089 (12)
C12—H5	1.089 (11)	C29—H23	1.089 (10)
C12—H6	1.089 (11)	C30—O8	1.357 (7)
C13—S1	1.798 (5)	C30—O9	1.246 (8)
C13—C17	1.409 (5)	C30—C29	1.474 (7)
C13—C18	1.421 (6)	H1—O8	0.993 (7)
C14—O5	1.491 (9)	H2—C10	1.089 (9)
C14—C21	1.410 (14)	H3—C11	1.089 (11)
C14—H7	1.089 (11)	H4—C11	1.088 (10)
C14—H8	1.089 (11)	H5—C12	1.089 (11)
C15—O6	1.319 (6)	H6—C12	1.089 (11)
C15—C22	1.352 (6)	H7—C14	1.089 (11)
C15—C23	1.371 (7)	H8—C14	1.089 (11)
C16—C17	1.396 (4)	H9—C17	1.089 (6)
C16—C19	1.403 (6)	H10—C18	1.089 (7)
C16—C25	1.494 (6)	H11—C20	1.089 (7)
C17—C13	1.409 (5)	H12—C21	1.089 (13)
C17—C16	1.396 (4)	H13—C21	1.088 (13)
C17—H9	1.089 (6)	H14—C21	1.090 (13)
C18—C13	1.421 (6)	H15—C22	1.089 (6)
C18—C20	1.414 (6)	H16—C23	1.089 (8)
C18—H10	1.089 (7)	H17—C25	1.089 (9)
C19—O7	1.370 (6)	H18—C25	1.089 (9)
C19—C16	1.403 (6)	H19—C25	1.089 (10)
C19—C20	1.387 (6)	H20—C26	1.089 (7)
C20—C18	1.414 (6)	H21—C27	1.090 (7)
C20—C19	1.387 (6)	H22—C29	1.089 (12)
C20—H11	1.089 (7)	H23—C29	1.089 (10)

C11—S1—C13	104.0 (4)	C16—C19—C20	120.2 (4)
C10—O5—C14	113.8 (5)	C18—C20—C19	120.0 (4)
C12—O6—C15	118.4 (6)	C18—C20—H11	120.1 (7)
C19—O7—C29	121.1 (6)	C19—C20—H11	119.9 (7)
C30—O8—H1	109.5 (7)	C14—C21—H12	109.5 (12)
O5—C10—C11	104.0 (6)	C14—C21—H13	109.5 (11)
O5—C10—C12	110.9 (7)	H12—C21—H13	109.5 (11)
C11—C10—C12	112.3 (7)	C14—C21—H14	109.4 (11)
O5—C10—H2	109.9 (7)	H12—C21—H14	109.4 (11)
C11—C10—H2	109.8 (9)	H13—C21—H14	109.5 (12)
C12—C10—H2	109.8 (8)	C15—C22—C26	119.7 (3)
S1—C11—C10	114.9 (6)	C15—C22—H15	120.1 (7)
S1—C11—H3	108.1 (6)	C26—C22—H15	120.1 (7)
C10—C11—H3	108.1 (8)	C15—C23—C27	117.5 (5)
S1—C11—H4	108.1 (7)	C15—C23—H16	121.3 (8)
C10—C11—H4	108.1 (8)	C27—C23—H16	121.2 (7)
H3—C11—H4	109.5 (8)	C26—C24—C27	118.1 (3)
O6—C12—C10	108.8 (6)	C26—C24—C28	120.8 (4)
O6—C12—H5	109.6 (10)	C27—C24—C28	121.1 (4)
C10—C12—H5	109.7 (9)	C16—C25—H17	109.3 (6)
O6—C12—H6	109.6 (10)	C16—C25—H18	109.4 (9)
C10—C12—H6	109.7 (8)	H17—C25—H18	109.5 (8)
H5—C12—H6	109.5 (7)	C16—C25—H19	109.5 (8)
S1—C13—C17	117.5 (5)	H17—C25—H19	109.7 (8)
S1—C13—C18	123.5 (6)	H18—C25—H19	109.5 (7)
C17—C13—C18	119.0 (3)	C22—C26—C24	120.7 (4)
O5—C14—C21	107.7 (8)	C22—C26—H20	119.7 (6)
O5—C14—H7	109.9 (11)	C24—C26—H20	119.7 (7)
C21—C14—H7	109.9 (10)	C23—C27—C24	121.1 (4)
O5—C14—H8	109.9 (8)	C23—C27—H21	119.5 (6)
C21—C14—H8	109.9 (12)	C24—C27—H21	119.4 (6)
H7—C14—H8	109.5 (9)	F2—C28—F3	112.4 (6)
O6—C15—C22	117.8 (6)	F2—C28—F4	95.3 (6)
O6—C15—C23	119.5 (7)	F3—C28—F4	103.8 (6)
C22—C15—C23	120.7 (4)	F2—C28—C24	116.4 (6)
C17—C16—C19	118.6 (3)	F3—C28—C24	114.2 (5)
C17—C16—C25	118.3 (4)	F4—C28—C24	112.4 (5)
C19—C16—C25	121.1 (4)	O7—C29—C30	118.6 (7)
C13—C17—C16	121.2 (3)	O7—C29—H22	107.1 (8)
C13—C17—H9	119.3 (6)	C30—C29—H22	107.1 (11)
C16—C17—H9	119.4 (6)	O7—C29—H23	107.1 (8)
C13—C18—C20	118.9 (4)	C30—C29—H23	107.2 (11)
C13—C18—H10	120.6 (7)	H22—C29—H23	109.5 (8)
C20—C18—H10	120.5 (8)	O8—C30—O9	124.0 (6)
O7—C19—C16	112.9 (5)	O8—C30—C29	113.2 (6)
O7—C19—C20	123.2 (6)	O9—C30—C29	122.3 (6)

(seladelpar_VASP) top

Crystal data top

C₂₁H₂₃F₃O₅S	b = 10.62563 Å
M_r = 444.46	c = 23.57851 Å
Orthorhombic, P2₁2₁2₁	V = 2218.97 Å³
a = 8.85689 Å	Z = 4

Data collection top

h = →	l = →
k = →

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

	x	y	z	B_iso*/B_eq
S1	−0.06226	0.81067	0.29800
F2	0.77456	0.54746	0.09473
F3	0.71686	0.74416	0.07619
F4	0.56934	0.59128	0.04659
O5	0.21714	0.62095	0.40710
O6	0.32888	0.66722	0.29666
O7	0.31495	0.92206	0.09562
O8	0.50360	1.22795	0.08729
O9	0.25766	1.17937	0.08604
C10	0.11756	0.64131	0.35934
C11	0.06945	0.77962	0.35565
C12	0.19659	0.59245	0.30683
C13	0.05734	0.84570	0.23965
C14	0.14147	0.61905	0.46174
C15	0.40328	0.65185	0.24652
C16	0.12593	0.80438	0.14067
C17	0.04109	0.77718	0.18907
C18	0.16162	0.94442	0.24135
C19	0.23206	0.90300	0.14406
C20	0.24941	0.97255	0.19398
C21	0.24516	0.55791	0.50448
C22	0.52414	0.73468	0.23699
C23	0.36658	0.56059	0.20585
C24	0.56755	0.63829	0.14545
C25	0.11139	0.72919	0.08716
C26	0.60502	0.72797	0.18674
C27	0.44978	0.55388	0.15579
C28	0.65496	0.63091	0.09138
C29	0.43670	1.00800	0.09718
C30	0.38886	1.14525	0.08996
H1	0.60569	1.18687	0.09182
H2	0.01570	0.58277	0.36528
H3	0.16772	0.84182	0.35156
H4	0.00738	0.80551	0.39423
H5	0.22856	0.49313	0.31316
H6	0.11867	0.59834	0.27056
H7	0.11314	0.71583	0.47476
H8	0.03500	0.56616	0.45721
H9	−0.03852	0.69872	0.18759
H10	0.17493	1.00072	0.27971
H11	0.32779	1.05128	0.19648
H12	0.35153	0.61041	0.50867
H13	0.26913	0.45973	0.49293
H14	0.19102	0.55929	0.54627
H15	0.55108	0.80474	0.26919
H16	0.27245	0.49580	0.21180
H17	0.02872	0.65325	0.09216
H18	0.22091	0.68798	0.07532
H19	0.07661	0.78864	0.05126
H20	0.69791	0.79322	0.17921
H21	0.42195	0.48166	0.12463
H22	0.50381	0.99822	0.13638
H23	0.51065	0.98199	0.06162

Torsion angles (º) top

C13—S1—C11—C10	−89.2	C11—C10—O5—C14	75.6
S1—C11—C10—C12	60.4	C10—O5—C14—C21	162.4
O5—C10—C11—S1	−177.7	C10—C12—O6—C15	−169.8
C17—C13—S1—C11	125.4	O5—C10—C12—O6	−64.9
C18—C13—S1—C11	−58.4	C19—O7—C29—C30	−82.2
C11—C10—C12—O6	58.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H1···O5ⁱ	1.01	1.72	2.725	175
C23—H16···S1ⁱⁱ	1.09	2.72	3.785	166

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Acknowledgements

Use of the Advanced Photon Source at Argonne National Laboratory was supported by the US Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02–06CH11357. We thank Saul Lapidus for his assistance in the data collection. We also thank the ICDD team – Steve Trimble, and Dave Bohnenberger – for their contribution to research, sample preparation, and in-house XRD data collection and verification.

Funding information

Funding for this research was provided by: International Centre for Diffraction Data (grant No. 09-03).

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