Architecture of the rings of 5-aryl­idenerhodanine derivatives versus P-gp inhibition

Żesławska, E.; Nitek, W.; Szymańska, E.; Tejchman, W.

doi:10.1107/S2053229623006502

Architecture of the rings of 5-arylidenerhodanine derivatives versus P-gp inhibition

W. Nitek, E. Szymańska, W. Tejchman and E. Żesławska

5-Arylidene derivatives of rhodanine show various biological activities. The new crystal structures of five derivatives investigated towards ABCB1 efflux pump modulation are reported, namely, 2-[5-([1,1′-biphenyl]-4-ylmethylidene]-4-oxo-2-thioxothiazolidin-3-yl)acetic acid dimethyl sulfoxide monosolvate, C₁₈H₁₃NO₃S₂·C₂H₆OS (1), 4-[5-([1,1′-biphenyl]-4-ylmethylidene]-4-oxo-2-thioxothiazolidin-3-yl)butanoic acid, C₂₀H₁₇NO₃S₂ (2), 5-[4-(benzyloxy)benzylidene]-2-thioxothiazolidin-4-one, C₁₇H₁₃NO₂S₂ (3), 4-{5-[4-(benzyloxy)benzylidene]-4-oxo-2-thioxothiazolidin-3-yl}butanoic acid, C₂₁H₁₉NO₄S₂ (4), and 5-[4-(diphenylamino)benzylidene]-2-thioxothiazolidin-4-one, C₂₂H₁₆N₂OS₂ (5). Compounds 1 and 3–5 crystallize in the triclinic space group P $\overline 1$ , while 2 crystallizes in the monoclinic space group P2₁/n, where the biphenyl moiety is observed in two positions (A and B). Two molecules are present in the asymmetric unit of 5 and, for the other four compounds, there is only one molecule; moreover, 1 crystallizes with one dimethyl sulfoxide molecule. The packing of the molecules containing a carboxyl group (1, 2 and 4) is determined by O—H

O hydrogen bonds, while in the other two compounds (3 and 5), the packing is determined by N—H

O hydrogen bonds. Additionally, induced-fit docking studies have been performed for the active compounds to investigate their putative binding mode inside the human glycoprotein P (P-gp) binding pocket.

Keywords: 5-arylidenerhodanine derivatives; efflux pump inhibitor; crystal structure; hydrogen bonding; induced-fit docking.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229623006502/yp3230sup1.cif Contains datablocks global, 1, 2, 3, 4, 5
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32301sup2.hkl Contains datablock 1
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32301sup7.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32302sup3.hkl Contains datablock 2
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32302sup8.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32303sup4.hkl Contains datablock 3
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32303sup9.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32304sup10.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32304sup5.hkl Contains datablock 4
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32305sup11.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32305sup6.hkl Contains datablock 5

CCDC references: 2284957; 2284958; 2284959; 2284960; 2284961; 2284957; 2284958

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018) for (1), (2); CrysAlis PRO (Rigaku OD, 2022) for (3); CrysAlis PRO (Rigaku OD, 2015) for (4), (5). Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for (1), (2); CrysAlis PRO (Rigaku OD, 2022) for (3); CrysAlis PRO (Rigaku OD, 2015) for (4), (5). Data reduction: CrysAlis PRO (Rigaku OD, 2018) for (1), (2); CrysAlis PRO (Rigaku OD, 2022) for (3); CrysAlis PRO (Rigaku OD, 2015) for (4), (5). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (1), (5); SIR2014 (Burla et al., 2015) for (2), (4); SIR2011 (Burla et al., 2012) for (3). For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: Mercury (Macrae et al., 2020) for (1), (3), (4), (5); ORTEP-3 for Windows (Farrugia, 2012) for (2). For all structures, software used to prepare material for publication: publCIF (Westrip, 2010).

2-(5-([1,1'-Biphenyl]-4-ylmethylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (1) top

Crystal data top

C₁₈H₁₃NO₃S₂·C₂H₆OS	Z = 2
M_r = 433.54	F(000) = 452
Triclinic, P1	D_x = 1.462 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3704 (1) Å	Cell parameters from 78214 reflections
b = 8.7100 (1) Å	θ = 2.4–51.7°
c = 16.4236 (1) Å	µ = 0.40 mm⁻¹
α = 98.680 (1)°	T = 100 K
β = 93.614 (1)°	Needle, light yellow
γ = 107.977 (1)°	0.93 × 0.17 × 0.06 mm
V = 984.62 (2) Å³

Data collection top

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	22177 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	17468 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.034
ω scans	θ_max = 51.9°, θ_min = 2.5°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −16→16
T_min = 0.496, T_max = 1	k = −19→19
156355 measured reflections	l = −36→36

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0507P)² + 0.0529P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
22177 reflections	Δρ_max = 0.62 e Å⁻³
259 parameters	Δρ_min = −0.55 e Å⁻³

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
C18	1.13614 (6)	0.91387 (5)	0.34413 (2)	0.01650 (6)
H18	1.161467	0.973975	0.300112	0.02*
C17	1.22018 (7)	0.98952 (5)	0.42436 (3)	0.01990 (7)
H17	1.302186	1.10027	0.434528	0.024*
C16	1.18472 (7)	0.90374 (6)	0.48981 (3)	0.02020 (7)
H16	1.242517	0.955247	0.544532	0.024*
C15	1.06376 (7)	0.74183 (6)	0.47422 (3)	0.01881 (6)
H15	1.038582	0.682687	0.518606	0.023*
C14	0.97924 (6)	0.66574 (5)	0.39395 (2)	0.01619 (5)
H14	0.896602	0.555226	0.384254	0.019*
C13	1.01464 (5)	0.75036 (5)	0.32713 (2)	0.01310 (5)
C10	0.92967 (5)	0.66943 (4)	0.24103 (2)	0.01260 (4)
C11	1.00447 (5)	0.73464 (5)	0.17238 (2)	0.01433 (5)
H11	1.110217	0.833365	0.18107	0.017*
C12	0.92589 (5)	0.65672 (5)	0.09207 (2)	0.01425 (5)
H12	0.978551	0.703521	0.046699	0.017*
C7	0.77000 (5)	0.50997 (5)	0.07645 (2)	0.01312 (5)
C8	0.69458 (6)	0.44480 (5)	0.14499 (2)	0.01490 (5)
H8	0.588976	0.34598	0.136363	0.018*
C9	0.77305 (6)	0.52358 (5)	0.22512 (2)	0.01454 (5)
H9	0.719332	0.477556	0.270509	0.017*
C6	0.69889 (5)	0.43480 (5)	−0.00947 (2)	0.01400 (5)
H6	0.766669	0.490948	−0.049254	0.017*
C5	0.55140 (5)	0.29748 (5)	−0.04161 (2)	0.01363 (5)
C4	0.50873 (6)	0.24339 (5)	−0.13265 (2)	0.01416 (5)
N3	0.35370 (5)	0.09788 (4)	−0.15123 (2)	0.01454 (4)
C2	0.27093 (6)	0.03606 (5)	−0.08568 (2)	0.01483 (5)
O1	0.59204 (5)	0.31031 (5)	−0.18570 (2)	0.01887 (5)
C19	0.29317 (6)	0.01487 (5)	−0.23614 (2)	0.01622 (5)
H19A	0.312643	0.097191	−0.273021	0.019*
H19B	0.154403	−0.047909	−0.242445	0.019*
C20	0.40484 (6)	−0.10124 (5)	−0.26202 (2)	0.01392 (5)
O3	0.33248 (6)	−0.18963 (5)	−0.33648 (2)	0.01985 (5)
O2	0.54190 (5)	−0.10860 (4)	−0.22010 (2)	0.01785 (5)
C21	0.24174 (8)	0.39188 (6)	0.28782 (3)	0.02420 (8)
H21A	0.344646	0.413202	0.2519	0.036*
H21B	0.15265	0.450463	0.274659	0.036*
H21C	0.172411	0.273833	0.278776	0.036*
C22	0.47559 (7)	0.66789 (5)	0.38776 (3)	0.01811 (6)
H22A	0.551131	0.723411	0.441287	0.027*
H22B	0.38637	0.725725	0.373643	0.027*
H22C	0.561965	0.667899	0.344775	0.027*
O4	0.49357 (6)	0.37900 (4)	0.40755 (2)	0.02072 (6)
S1	0.38727 (2)	0.16147 (2)	0.00822 (2)	0.01444 (2)
S2	0.08731 (2)	−0.13058 (2)	−0.09188 (2)	0.02106 (2)
S3	0.34337 (2)	0.46175 (2)	0.39428 (2)	0.01640 (2)
H3	0.4027 (14)	−0.2477 (13)	−0.3517 (6)	0.030 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C18	0.02011 (14)	0.01330 (12)	0.01480 (12)	0.00382 (11)	0.00008 (10)	0.00273 (9)
C17	0.02559 (18)	0.01445 (13)	0.01618 (13)	0.00300 (12)	−0.00130 (12)	0.00098 (10)
C16	0.02530 (18)	0.01894 (15)	0.01380 (12)	0.00502 (13)	−0.00050 (12)	0.00086 (11)
C15	0.02104 (16)	0.02041 (16)	0.01338 (12)	0.00404 (13)	0.00125 (11)	0.00407 (11)
C14	0.01617 (13)	0.01693 (13)	0.01401 (11)	0.00269 (11)	0.00082 (10)	0.00431 (10)
C13	0.01290 (11)	0.01378 (11)	0.01270 (10)	0.00437 (9)	0.00094 (8)	0.00267 (8)
C10	0.01239 (11)	0.01335 (11)	0.01245 (10)	0.00462 (9)	0.00099 (8)	0.00271 (8)
C11	0.01311 (11)	0.01539 (12)	0.01402 (11)	0.00347 (10)	0.00159 (9)	0.00363 (9)
C12	0.01389 (11)	0.01633 (12)	0.01301 (11)	0.00479 (10)	0.00225 (9)	0.00400 (9)
C7	0.01367 (11)	0.01433 (11)	0.01228 (10)	0.00584 (9)	0.00160 (8)	0.00235 (8)
C8	0.01593 (12)	0.01444 (12)	0.01271 (11)	0.00274 (10)	0.00132 (9)	0.00217 (9)
C9	0.01570 (12)	0.01435 (12)	0.01240 (11)	0.00297 (10)	0.00165 (9)	0.00276 (9)
C6	0.01501 (12)	0.01591 (12)	0.01201 (10)	0.00643 (10)	0.00159 (9)	0.00225 (9)
C5	0.01504 (12)	0.01575 (12)	0.01138 (10)	0.00704 (10)	0.00145 (8)	0.00195 (9)
C4	0.01529 (12)	0.01747 (13)	0.01146 (10)	0.00794 (10)	0.00140 (9)	0.00226 (9)
N3	0.01596 (11)	0.01697 (11)	0.01112 (9)	0.00688 (9)	0.00099 (8)	0.00076 (8)
C2	0.01610 (12)	0.01578 (12)	0.01328 (11)	0.00661 (10)	0.00131 (9)	0.00166 (9)
O1	0.02088 (12)	0.02341 (14)	0.01312 (10)	0.00707 (11)	0.00347 (9)	0.00526 (9)
C19	0.01814 (13)	0.01971 (14)	0.01165 (11)	0.00903 (12)	−0.00094 (9)	0.00029 (10)
C20	0.01661 (12)	0.01453 (12)	0.01096 (10)	0.00553 (10)	0.00169 (9)	0.00222 (8)
O3	0.02588 (14)	0.02153 (13)	0.01255 (9)	0.01128 (11)	−0.00146 (9)	−0.00189 (9)
O2	0.01904 (12)	0.02137 (13)	0.01506 (10)	0.01006 (10)	−0.00006 (8)	0.00240 (9)
C21	0.02391 (19)	0.01864 (16)	0.02626 (19)	0.00618 (14)	−0.00689 (15)	−0.00198 (14)
C22	0.02107 (15)	0.01378 (13)	0.01835 (14)	0.00484 (11)	0.00039 (11)	0.00190 (10)
O4	0.03026 (16)	0.01797 (12)	0.01694 (11)	0.01369 (12)	−0.00031 (10)	0.00100 (9)
S1	0.01642 (4)	0.01568 (4)	0.01130 (3)	0.00547 (3)	0.00169 (2)	0.00200 (2)
S2	0.02223 (5)	0.01836 (4)	0.01866 (4)	0.00141 (4)	0.00123 (3)	0.00277 (3)
S3	0.01813 (4)	0.01392 (4)	0.01787 (4)	0.00518 (3)	0.00458 (3)	0.00394 (3)

Geometric parameters (Å, º) top

C18—C17	1.3918 (6)	C6—H6	0.95
C18—C13	1.4034 (5)	C5—C4	1.4808 (5)
C18—H18	0.95	C5—S1	1.7519 (4)
C17—C16	1.3926 (7)	C4—O1	1.2149 (5)
C17—H17	0.95	C4—N3	1.3965 (5)
C16—C15	1.3911 (7)	N3—C2	1.3697 (5)
C16—H16	0.95	N3—C19	1.4438 (5)
C15—C14	1.3941 (6)	C2—S2	1.6352 (4)
C15—H15	0.95	C2—S1	1.7474 (4)
C14—C13	1.4060 (5)	C19—C20	1.5195 (5)
C14—H14	0.95	C19—H19A	0.99
C13—C10	1.4845 (5)	C19—H19B	0.99
C10—C9	1.4040 (5)	C20—O2	1.2100 (5)
C10—C11	1.4057 (5)	C20—O3	1.3239 (5)
C11—C12	1.3881 (5)	O3—H3	0.852 (10)
C11—H11	0.95	C21—S3	1.7946 (5)
C12—C7	1.4061 (5)	C21—H21A	0.98
C12—H12	0.95	C21—H21B	0.98
C7—C8	1.4055 (5)	C21—H21C	0.98
C7—C6	1.4527 (5)	C22—S3	1.7822 (4)
C8—C9	1.3870 (5)	C22—H22A	0.98
C8—H8	0.95	C22—H22B	0.98
C9—H9	0.95	C22—H22C	0.98
C6—C5	1.3511 (5)	O4—S3	1.5172 (4)

C17—C18—C13	121.15 (4)	C6—C5—C4	119.99 (3)
C17—C18—H18	119.4	C6—C5—S1	130.11 (3)
C13—C18—H18	119.4	C4—C5—S1	109.89 (3)
C18—C17—C16	120.36 (4)	O1—C4—N3	122.81 (3)
C18—C17—H17	119.8	O1—C4—C5	127.34 (4)
C16—C17—H17	119.8	N3—C4—C5	109.85 (3)
C15—C16—C17	119.31 (4)	C2—N3—C4	117.03 (3)
C15—C16—H16	120.3	C2—N3—C19	122.73 (4)
C17—C16—H16	120.3	C4—N3—C19	120.17 (3)
C16—C15—C14	120.48 (4)	N3—C2—S2	125.95 (3)
C16—C15—H15	119.8	N3—C2—S1	110.70 (3)
C14—C15—H15	119.8	S2—C2—S1	123.35 (2)
C15—C14—C13	120.89 (4)	N3—C19—C20	111.45 (3)
C15—C14—H14	119.6	N3—C19—H19A	109.3
C13—C14—H14	119.6	C20—C19—H19A	109.3
C18—C13—C14	117.81 (3)	N3—C19—H19B	109.3
C18—C13—C10	120.74 (3)	C20—C19—H19B	109.3
C14—C13—C10	121.43 (3)	H19A—C19—H19B	108
C9—C10—C11	117.51 (3)	O2—C20—O3	125.60 (4)
C9—C10—C13	121.18 (3)	O2—C20—C19	123.98 (3)
C11—C10—C13	121.31 (3)	O3—C20—C19	110.41 (3)
C12—C11—C10	120.89 (3)	C20—O3—H3	109.0 (7)
C12—C11—H11	119.6	S3—C21—H21A	109.5
C10—C11—H11	119.6	S3—C21—H21B	109.5
C11—C12—C7	121.39 (3)	H21A—C21—H21B	109.5
C11—C12—H12	119.3	S3—C21—H21C	109.5
C7—C12—H12	119.3	H21A—C21—H21C	109.5
C8—C7—C12	117.83 (3)	H21B—C21—H21C	109.5
C8—C7—C6	124.33 (3)	S3—C22—H22A	109.5
C12—C7—C6	117.84 (3)	S3—C22—H22B	109.5
C9—C8—C7	120.55 (3)	H22A—C22—H22B	109.5
C9—C8—H8	119.7	S3—C22—H22C	109.5
C7—C8—H8	119.7	H22A—C22—H22C	109.5
C8—C9—C10	121.84 (3)	H22B—C22—H22C	109.5
C8—C9—H9	119.1	C2—S1—C5	92.503 (18)
C10—C9—H9	119.1	O4—S3—C22	105.27 (2)
C5—C6—C7	130.07 (4)	O4—S3—C21	106.39 (2)
C5—C6—H6	115	C22—S3—C21	98.47 (2)
C7—C6—H6	115

C13—C18—C17—C16	−0.11 (7)	C12—C7—C6—C5	−178.76 (4)
C18—C17—C16—C15	−0.26 (8)	C7—C6—C5—C4	−178.80 (4)
C17—C16—C15—C14	0.21 (8)	C7—C6—C5—S1	1.72 (7)
C16—C15—C14—C13	0.21 (7)	C6—C5—C4—O1	−0.76 (6)
C17—C18—C13—C14	0.51 (6)	S1—C5—C4—O1	178.82 (4)
C17—C18—C13—C10	−178.42 (4)	C6—C5—C4—N3	178.85 (3)
C15—C14—C13—C18	−0.56 (6)	S1—C5—C4—N3	−1.57 (4)
C15—C14—C13—C10	178.36 (4)	O1—C4—N3—C2	−179.25 (4)
C18—C13—C10—C9	−163.79 (4)	C5—C4—N3—C2	1.12 (5)
C14—C13—C10—C9	17.31 (6)	O1—C4—N3—C19	3.82 (6)
C18—C13—C10—C11	17.06 (6)	C5—C4—N3—C19	−175.81 (3)
C14—C13—C10—C11	−161.83 (4)	C4—N3—C2—S2	179.30 (3)
C9—C10—C11—C12	−0.17 (6)	C19—N3—C2—S2	−3.85 (6)
C13—C10—C11—C12	179.01 (3)	C4—N3—C2—S1	−0.14 (4)
C10—C11—C12—C7	−0.33 (6)	C19—N3—C2—S1	176.71 (3)
C11—C12—C7—C8	0.52 (6)	C2—N3—C19—C20	−89.99 (5)
C11—C12—C7—C6	−178.83 (3)	C4—N3—C19—C20	86.77 (4)
C12—C7—C8—C9	−0.20 (6)	N3—C19—C20—O2	−8.07 (6)
C6—C7—C8—C9	179.09 (4)	N3—C19—C20—O3	172.83 (4)
C7—C8—C9—C10	−0.30 (6)	N3—C2—S1—C5	−0.71 (3)
C11—C10—C9—C8	0.48 (6)	S2—C2—S1—C5	179.84 (3)
C13—C10—C9—C8	−178.69 (4)	C6—C5—S1—C2	−179.18 (4)
C8—C7—C6—C5	1.94 (7)	C4—C5—S1—C2	1.30 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.85 (1)	1.75 (1)	2.5768 (5)	165 (1)
C12—H12···S2ⁱⁱ	0.95	2.9	3.8415 (4)	170
C17—H17···O4ⁱⁱ	0.95	2.52	3.4320 (6)	160
C16—H16···O3ⁱⁱⁱ	0.95	2.64	3.2927 (6)	127
C8—H8···O2ⁱ	0.95	2.63	3.3683 (5)	135
C21—H21A···O1^iv	0.98	2.71	3.2638 (7)	116

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

4-(5-([1,1'-Biphenyl]-4-ylmethylidene)-4-oxo-2-thioxothiazolidin-3-yl)butanoic acid (2) top

Crystal data top

C₂₀H₁₇NO₃S₂	F(000) = 800
M_r = 383.46	D_x = 1.42 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 37361 reflections
a = 5.14350 (4) Å	θ = 4.0–76.4°
b = 66.3783 (5) Å	µ = 2.86 mm⁻¹
c = 5.34343 (5) Å	T = 100 K
β = 100.4548 (8)°	Plate, colourless
V = 1794.05 (3) Å³	0.16 × 0.12 × 0.02 mm
Z = 4

Data collection top

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	3746 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3694 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
ω scans	θ_max = 76.6°, θ_min = 4.0°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −6→5
T_min = 0.637, T_max = 1	k = −83→82
55674 measured reflections	l = −6→6

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0097P)² + 2.0556P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.076	(Δ/σ)_max = 0.001
S = 1.15	Δρ_max = 0.31 e Å⁻³
3746 reflections	Δρ_min = −0.23 e Å⁻³
310 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00037 (8)
Primary atom site location: structure-invariant direct methods

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.83155 (9)	0.10860 (2)	0.05764 (9)	0.02083 (11)
S2	1.06564 (8)	0.08008 (2)	−0.26499 (8)	0.01863 (11)
O2	1.3471 (2)	0.01197 (2)	0.2478 (2)	0.0196 (3)
O3	1.2570 (2)	0.01440 (2)	0.6408 (2)	0.0210 (3)
H3	1.386054	0.006481	0.674449	0.031*
C23	1.2143 (3)	0.01878 (2)	0.3962 (3)	0.0151 (3)
C22	0.9883 (3)	0.03311 (2)	0.3196 (3)	0.0159 (3)
H22A	1.035861	0.046387	0.399369	0.019*
H22B	0.831763	0.028034	0.383906	0.019*
C21	0.9175 (3)	0.03573 (2)	0.0331 (3)	0.0164 (3)
H21A	0.876022	0.022348	−0.045974	0.02*
H21B	1.073519	0.041087	−0.029569	0.02*
C20	0.6841 (3)	0.04972 (2)	−0.0531 (3)	0.0158 (3)
H20A	0.64683	0.050053	−0.241414	0.019*
H20B	0.526722	0.044017	0.003651	0.019*
N3	0.7219 (3)	0.07062 (2)	0.0419 (3)	0.0141 (3)
C2	0.8719 (3)	0.08435 (2)	−0.0589 (3)	0.0164 (3)
C4	0.5761 (3)	0.07809 (2)	0.2198 (3)	0.0152 (3)
C5	0.6089 (3)	0.10026 (2)	0.2457 (3)	0.0165 (3)
O1	0.4417 (2)	0.06758 (2)	0.3308 (2)	0.0188 (3)
C6	0.4731 (3)	0.11055 (3)	0.3959 (3)	0.0185 (3)
H6	0.36895	0.102349	0.485021	0.022*
C7	0.4566 (3)	0.13198 (3)	0.4469 (3)	0.0184 (3)
C10	0.3875 (4)	0.17305 (3)	0.5628 (4)	0.0229 (4)
C13	0.3470 (4)	0.19458 (3)	0.6220 (4)	0.0267 (4)
C16	0.2597 (5)	0.23498 (3)	0.7358 (5)	0.0380 (5)
H16	0.239554	0.248731	0.777882	0.046*	0.508 (3)
H16A	0.227423	0.248892	0.758843	0.046*	0.492 (3)
C18A	0.2906 (8)	0.20890 (6)	0.4176 (9)	0.0314 (9)	0.508 (3)
H18A	0.283828	0.204714	0.246524	0.038*	0.508 (3)
C17A	0.2461 (8)	0.22897 (6)	0.4726 (9)	0.0360 (10)	0.508 (3)
H17A	0.207272	0.238602	0.339604	0.043*	0.508 (3)
C14A	0.3474 (8)	0.20106 (6)	0.8619 (8)	0.0322 (9)	0.508 (3)
H14A	0.380695	0.191643	0.997767	0.039*	0.508 (3)
C15A	0.3004 (9)	0.22114 (6)	0.9162 (9)	0.0374 (11)	0.508 (3)
H15A	0.297649	0.224957	1.087042	0.045*	0.508 (3)
C12A	0.6268 (10)	0.14680 (7)	0.3876 (10)	0.0226 (10)	0.508 (3)
H12A	0.766731	0.143084	0.302722	0.027*	0.508 (3)
C11A	0.5974 (10)	0.16678 (6)	0.4492 (10)	0.0244 (9)	0.508 (3)
H11A	0.722288	0.176413	0.413533	0.029*	0.508 (3)
C9A	0.2211 (11)	0.15826 (9)	0.6317 (11)	0.0228 (11)	0.508 (3)
H9A	0.084278	0.162002	0.720384	0.027*	0.508 (3)
C8A	0.2525 (11)	0.13822 (9)	0.5729 (11)	0.0229 (11)	0.508 (3)
H8A	0.134027	0.128466	0.618277	0.027*	0.508 (3)
C18B	0.5650 (8)	0.20787 (6)	0.6876 (8)	0.0288 (9)	0.492 (3)
H18B	0.739669	0.203079	0.691381	0.035*	0.492 (3)
C17B	0.5234 (9)	0.22789 (6)	0.7463 (9)	0.0330 (10)	0.492 (3)
H17B	0.669154	0.236763	0.792873	0.04*	0.492 (3)
C14B	0.0991 (8)	0.20192 (6)	0.6353 (8)	0.0297 (9)	0.492 (3)
H14B	−0.048072	0.193039	0.603739	0.036*	0.492 (3)
C15B	0.0584 (9)	0.22196 (6)	0.6935 (9)	0.0339 (10)	0.492 (3)
H15B	−0.114784	0.226449	0.703302	0.041*	0.492 (3)
C12B	0.5327 (11)	0.14716 (7)	0.2922 (10)	0.0232 (10)	0.492 (3)
H12B	0.610135	0.143628	0.149845	0.028*	0.492 (3)
C11B	0.4954 (10)	0.16736 (7)	0.3461 (10)	0.0250 (10)	0.492 (3)
H11B	0.542655	0.177471	0.236745	0.03*	0.492 (3)
C9B	0.3101 (11)	0.15784 (10)	0.7101 (12)	0.0227 (12)	0.492 (3)
H9B	0.232177	0.16127	0.852604	0.027*	0.492 (3)
C8B	0.3432 (11)	0.13778 (9)	0.6552 (11)	0.0217 (11)	0.492 (3)
H8B	0.288087	0.127715	0.76071	0.026*	0.492 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0223 (2)	0.01499 (19)	0.0284 (2)	−0.00131 (16)	0.01314 (17)	0.00002 (16)
S2	0.0173 (2)	0.0205 (2)	0.0197 (2)	0.00009 (15)	0.00783 (15)	0.00062 (15)
O2	0.0179 (6)	0.0229 (6)	0.0190 (6)	0.0060 (5)	0.0063 (5)	0.0018 (5)
O3	0.0220 (6)	0.0245 (6)	0.0168 (6)	0.0098 (5)	0.0046 (5)	0.0021 (5)
C23	0.0141 (8)	0.0140 (7)	0.0174 (8)	−0.0026 (6)	0.0033 (6)	−0.0001 (6)
C22	0.0146 (8)	0.0155 (7)	0.0182 (8)	0.0013 (6)	0.0046 (6)	−0.0001 (6)
C21	0.0145 (8)	0.0171 (8)	0.0177 (8)	0.0026 (6)	0.0036 (6)	0.0003 (6)
C20	0.0139 (7)	0.0151 (7)	0.0184 (8)	−0.0006 (6)	0.0027 (6)	−0.0013 (6)
N3	0.0108 (6)	0.0155 (6)	0.0165 (7)	0.0010 (5)	0.0033 (5)	0.0013 (5)
C2	0.0139 (8)	0.0171 (8)	0.0175 (8)	0.0006 (6)	0.0008 (6)	0.0021 (6)
C4	0.0122 (7)	0.0178 (8)	0.0153 (8)	0.0023 (6)	0.0016 (6)	0.0016 (6)
C5	0.0144 (8)	0.0170 (8)	0.0178 (8)	0.0002 (6)	0.0022 (6)	0.0021 (6)
O1	0.0176 (6)	0.0196 (6)	0.0207 (6)	−0.0013 (5)	0.0077 (5)	0.0014 (5)
C6	0.0175 (8)	0.0186 (8)	0.0200 (8)	0.0000 (6)	0.0046 (6)	0.0026 (6)
C7	0.0154 (8)	0.0188 (8)	0.0204 (8)	0.0021 (6)	0.0019 (6)	−0.0003 (6)
C10	0.0194 (9)	0.0194 (8)	0.0289 (10)	0.0019 (7)	0.0021 (7)	−0.0023 (7)
C13	0.0245 (9)	0.0193 (9)	0.0365 (11)	0.0014 (7)	0.0062 (8)	−0.0030 (8)
C16	0.0383 (12)	0.0180 (9)	0.0592 (15)	0.0017 (8)	0.0124 (11)	−0.0063 (9)
C18A	0.029 (2)	0.0219 (18)	0.043 (2)	0.0031 (15)	0.0064 (17)	0.0014 (16)
C17A	0.027 (2)	0.0208 (19)	0.060 (3)	0.0020 (15)	0.0083 (19)	0.0041 (18)
C14A	0.033 (2)	0.0238 (19)	0.038 (2)	0.0029 (16)	0.0015 (17)	−0.0048 (16)
C15A	0.034 (2)	0.028 (2)	0.049 (3)	0.0033 (17)	0.0048 (19)	−0.0141 (19)
C12A	0.018 (2)	0.023 (2)	0.028 (3)	0.0001 (19)	0.0088 (18)	−0.001 (2)
C11A	0.022 (2)	0.0196 (19)	0.034 (3)	−0.0010 (18)	0.0092 (19)	−0.0005 (19)
C9A	0.022 (3)	0.020 (2)	0.027 (3)	0.004 (2)	0.006 (2)	−0.003 (2)
C8A	0.021 (3)	0.020 (2)	0.029 (3)	0.002 (2)	0.008 (2)	0.000 (2)
C18B	0.026 (2)	0.0219 (19)	0.040 (2)	−0.0005 (15)	0.0084 (17)	−0.0053 (16)
C17B	0.037 (2)	0.0204 (19)	0.043 (2)	−0.0047 (17)	0.0088 (19)	−0.0063 (17)
C14B	0.027 (2)	0.0206 (19)	0.041 (2)	0.0023 (15)	0.0050 (17)	−0.0053 (16)
C15B	0.031 (2)	0.024 (2)	0.046 (3)	0.0080 (17)	0.0060 (19)	−0.0041 (18)
C12B	0.026 (3)	0.020 (2)	0.025 (3)	0.003 (2)	0.0066 (19)	−0.001 (2)
C11B	0.022 (2)	0.020 (2)	0.032 (3)	0.0021 (18)	0.0043 (19)	0.0041 (19)
C9B	0.022 (3)	0.024 (2)	0.021 (3)	0.004 (2)	0.003 (2)	−0.002 (2)
C8B	0.021 (3)	0.021 (2)	0.023 (3)	0.003 (2)	0.0046 (19)	0.002 (2)

Geometric parameters (Å, º) top

S1—C2	1.7522 (17)	C13—C14A	1.352 (5)
S1—C5	1.7449 (17)	C13—C18B	1.420 (4)
S2—C2	1.6384 (17)	C13—C14B	1.379 (4)
O2—C23	1.223 (2)	C16—H16	0.95
O3—H3	0.84	C16—H16A	0.95
O3—C23	1.318 (2)	C16—C17A	1.451 (5)
C23—C22	1.501 (2)	C16—C15A	1.320 (5)
C22—H22A	0.99	C16—C17B	1.427 (5)
C22—H22B	0.99	C16—C15B	1.336 (5)
C22—C21	1.518 (2)	C18A—H18A	0.95
C21—H21A	0.99	C18A—C17A	1.392 (5)
C21—H21B	0.99	C17A—H17A	0.95
C21—C20	1.522 (2)	C14A—H14A	0.95
C20—H20A	0.99	C14A—C15A	1.394 (5)
C20—H20B	0.99	C15A—H15A	0.95
C20—N3	1.477 (2)	C12A—H12A	0.95
N3—C2	1.366 (2)	C12A—C11A	1.382 (7)
N3—C4	1.404 (2)	C11A—H11A	0.95
C4—C5	1.485 (2)	C9A—H9A	0.95
C4—O1	1.210 (2)	C9A—C8A	1.383 (8)
C5—C6	1.343 (2)	C8A—H8A	0.95
C6—H6	0.95	C18B—H18B	0.95
C6—C7	1.454 (2)	C18B—C17B	1.391 (5)
C7—C12A	1.391 (5)	C17B—H17B	0.95
C7—C8A	1.408 (6)	C14B—H14B	0.95
C7—C12B	1.403 (5)	C14B—C15B	1.390 (5)
C7—C8B	1.401 (6)	C15B—H15B	0.95
C10—C13	1.487 (2)	C12B—H12B	0.95
C10—C11A	1.395 (5)	C12B—C11B	1.392 (7)
C10—C9A	1.395 (7)	C11B—H11B	0.95
C10—C11B	1.423 (5)	C9B—H9B	0.95
C10—C9B	1.383 (7)	C9B—C8B	1.381 (9)
C13—C18A	1.437 (4)	C8B—H8B	0.95

C5—S1—C2	92.62 (8)	C14B—C13—C18B	117.7 (3)
C23—O3—H3	109.5	C17A—C16—H16	120.4
O2—C23—O3	123.32 (15)	C15A—C16—H16	120.4
O2—C23—C22	123.60 (15)	C15A—C16—C17A	119.3 (3)
O3—C23—C22	113.07 (14)	C17B—C16—H16A	120.2
C23—C22—H22A	109.1	C15B—C16—H16A	120.2
C23—C22—H22B	109.1	C15B—C16—C17B	119.7 (3)
C23—C22—C21	112.32 (13)	C13—C18A—H18A	120.3
H22A—C22—H22B	107.9	C17A—C18A—C13	119.4 (4)
C21—C22—H22A	109.1	C17A—C18A—H18A	120.3
C21—C22—H22B	109.1	C16—C17A—H17A	120.4
C22—C21—H21A	108.8	C18A—C17A—C16	119.2 (4)
C22—C21—H21B	108.8	C18A—C17A—H17A	120.4
C22—C21—C20	113.99 (13)	C13—C14A—H14A	119
H21A—C21—H21B	107.7	C13—C14A—C15A	122.1 (4)
C20—C21—H21A	108.8	C15A—C14A—H14A	119
C20—C21—H21B	108.8	C16—C15A—C14A	121.6 (4)
C21—C20—H20A	108.5	C16—C15A—H15A	119.2
C21—C20—H20B	108.5	C14A—C15A—H15A	119.2
H20A—C20—H20B	107.5	C7—C12A—H12A	119.2
N3—C20—C21	114.96 (13)	C11A—C12A—C7	121.6 (4)
N3—C20—H20A	108.5	C11A—C12A—H12A	119.2
N3—C20—H20B	108.5	C10—C11A—H11A	119.4
C2—N3—C20	122.61 (14)	C12A—C11A—C10	121.2 (4)
C2—N3—C4	116.15 (13)	C12A—C11A—H11A	119.4
C4—N3—C20	120.75 (13)	C10—C9A—H9A	119.5
S2—C2—S1	121.56 (10)	C8A—C9A—C10	121.0 (5)
N3—C2—S1	111.16 (12)	C8A—C9A—H9A	119.5
N3—C2—S2	127.28 (13)	C7—C8A—H8A	119.4
N3—C4—C5	110.33 (13)	C9A—C8A—C7	121.3 (5)
O1—C4—N3	123.43 (15)	C9A—C8A—H8A	119.4
O1—C4—C5	126.23 (15)	C13—C18B—H18B	119.9
C4—C5—S1	109.65 (12)	C17B—C18B—C13	120.2 (4)
C6—C5—S1	130.55 (13)	C17B—C18B—H18B	119.9
C6—C5—C4	119.80 (15)	C16—C17B—H17B	120.3
C5—C6—H6	114.2	C18B—C17B—C16	119.3 (4)
C5—C6—C7	131.60 (16)	C18B—C17B—H17B	120.3
C7—C6—H6	114.2	C13—C14B—H14B	119.1
C12A—C7—C6	126.1 (2)	C13—C14B—C15B	121.8 (4)
C12A—C7—C8A	117.1 (3)	C15B—C14B—H14B	119.1
C8A—C7—C6	116.8 (3)	C16—C15B—C14B	120.9 (4)
C12B—C7—C6	124.1 (3)	C16—C15B—H15B	119.5
C8B—C7—C6	117.7 (3)	C14B—C15B—H15B	119.5
C8B—C7—C12B	118.1 (3)	C7—C12B—H12B	119.8
C11A—C10—C13	122.0 (2)	C11B—C12B—C7	120.4 (4)
C11A—C10—C9A	117.7 (3)	C11B—C12B—H12B	119.8
C9A—C10—C13	120.3 (3)	C10—C11B—H11B	119.6
C11B—C10—C13	121.3 (2)	C12B—C11B—C10	120.8 (4)
C9B—C10—C13	121.0 (3)	C12B—C11B—H11B	119.6
C9B—C10—C11B	117.7 (3)	C10—C9B—H9B	119.2
C18A—C13—C10	119.4 (2)	C8B—C9B—C10	121.6 (5)
C14A—C13—C10	122.1 (2)	C8B—C9B—H9B	119.2
C14A—C13—C18A	118.4 (3)	C7—C8B—H8B	119.4
C18B—C13—C10	121.0 (2)	C9B—C8B—C7	121.3 (5)
C14B—C13—C10	121.1 (2)	C9B—C8B—H8B	119.4

S1—C5—C6—C7	2.5 (3)	C10—C13—C18B—C17B	−179.0 (3)
O2—C23—C22—C21	8.5 (2)	C10—C13—C14B—C15B	179.2 (3)
O3—C23—C22—C21	−172.05 (14)	C10—C9A—C8A—C7	1.5 (7)
C23—C22—C21—C20	178.44 (13)	C10—C9B—C8B—C7	−0.1 (7)
C22—C21—C20—N3	60.87 (19)	C13—C10—C11A—C12A	−177.8 (4)
C21—C20—N3—C2	77.00 (19)	C13—C10—C9A—C8A	178.5 (4)
C21—C20—N3—C4	−111.39 (16)	C13—C10—C11B—C12B	180.0 (4)
C20—N3—C2—S1	169.93 (11)	C13—C10—C9B—C8B	179.1 (4)
C20—N3—C2—S2	−9.2 (2)	C13—C18A—C17A—C16	0.5 (5)
C20—N3—C4—C5	−168.71 (13)	C13—C14A—C15A—C16	−1.8 (6)
C20—N3—C4—O1	10.4 (2)	C13—C18B—C17B—C16	−1.0 (6)
N3—C4—C5—S1	−3.22 (16)	C13—C14B—C15B—C16	0.9 (7)
N3—C4—C5—C6	176.12 (15)	C18A—C13—C14A—C15A	−1.3 (5)
C2—S1—C5—C4	1.84 (12)	C17A—C16—C15A—C14A	4.1 (6)
C2—S1—C5—C6	−177.40 (17)	C14A—C13—C18A—C17A	1.8 (5)
C2—N3—C4—C5	3.43 (19)	C15A—C16—C17A—C18A	−3.5 (5)
C2—N3—C4—O1	−177.47 (15)	C12A—C7—C8A—C9A	0.8 (6)
C4—N3—C2—S1	−2.04 (18)	C11A—C10—C13—C18A	63.7 (4)
C4—N3—C2—S2	178.78 (12)	C11A—C10—C13—C14A	−119.9 (4)
C4—C5—C6—C7	−176.66 (17)	C11A—C10—C9A—C8A	−4.5 (6)
C5—S1—C2—S2	179.23 (11)	C9A—C10—C13—C18A	−119.5 (4)
C5—S1—C2—N3	0.00 (13)	C9A—C10—C13—C14A	56.9 (4)
C5—C6—C7—C12A	−14.6 (4)	C9A—C10—C11A—C12A	5.3 (6)
C5—C6—C7—C8A	166.9 (3)	C8A—C7—C12A—C11A	−0.1 (6)
C5—C6—C7—C12B	17.6 (4)	C18B—C13—C14B—C15B	4.3 (6)
C5—C6—C7—C8B	−166.3 (3)	C17B—C16—C15B—C14B	−6.2 (6)
O1—C4—C5—S1	177.70 (14)	C14B—C13—C18B—C17B	−4.1 (5)
O1—C4—C5—C6	−3.0 (3)	C15B—C16—C17B—C18B	6.3 (6)
C6—C7—C12A—C11A	−178.6 (4)	C12B—C7—C8B—C9B	−0.9 (6)
C6—C7—C8A—C9A	179.5 (4)	C11B—C10—C13—C18B	−65.1 (4)
C6—C7—C12B—C11B	176.0 (4)	C11B—C10—C13—C14B	120.2 (4)
C6—C7—C8B—C9B	−177.2 (4)	C11B—C10—C9B—C8B	2.0 (6)
C7—C12A—C11A—C10	−3.1 (7)	C9B—C10—C13—C18B	117.9 (4)
C7—C12B—C11B—C10	2.0 (7)	C9B—C10—C13—C14B	−56.8 (4)
C10—C13—C18A—C17A	178.4 (3)	C9B—C10—C11B—C12B	−2.9 (6)
C10—C13—C14A—C15A	−177.8 (3)	C8B—C7—C12B—C11B	0.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.83	2.669 (2)	176
C22—H22A···S2ⁱⁱ	0.99	2.85	3.806 (2)	162
C22—H22A···O1ⁱⁱⁱ	0.99	2.60	3.260 (2)	124
C21—H21B···S2	0.99	2.87	3.497 (2)	122
C20—H20A···O1^iv	0.99	2.61	3.509 (2)	151
C6—H6···S2^v	0.95	2.68	3.625 (2)	178

Symmetry codes: (i) −x+3, −y, −z+1; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x, y, z−1; (v) x−1, y, z+1.

5-(4-(Benzyloxy)benzylidene)-2-thioxothiazolidin-4-one (3) top

Crystal data top

C₁₇H₁₃NO₂S₂	Z = 2
M_r = 327.4	F(000) = 340
Triclinic, P1	D_x = 1.471 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0091 (10) Å	Cell parameters from 2831 reflections
b = 10.1386 (9) Å	θ = 3.7–27.9°
c = 10.8157 (12) Å	µ = 0.37 mm⁻¹
α = 93.484 (8)°	T = 100 K
β = 105.413 (11)°	Irregular, orange
γ = 90.916 (9)°	0.25 × 0.17 × 0.08 mm
V = 739.17 (16) Å³

Data collection top

Rigaku SuperNova Dual source diffractometer with an Atlas detector	3370 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2390 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.061
Detector resolution: 10.3756 pixels mm^-1	θ_max = 28.4°, θ_min = 2.7°
ω scans	h = −8→9
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022)	k = −13→12
T_min = 0.624, T_max = 1	l = −14→13
8387 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.076	H-atom parameters constrained
wR(F²) = 0.224	w = 1/[σ²(F_o²) + (0.1204P)² + 0.7354P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3370 reflections	Δρ_max = 0.85 e Å⁻³
199 parameters	Δρ_min = −0.86 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.78314 (14)	0.67205 (9)	1.13843 (8)	0.0244 (3)
S2	0.88064 (16)	0.87817 (9)	1.35525 (9)	0.0300 (3)
O1	0.9381 (4)	0.3904 (3)	1.3601 (3)	0.0297 (6)
C2	0.8654 (5)	0.7228 (4)	1.3011 (3)	0.0223 (8)
N3	0.9150 (5)	0.6158 (3)	1.3721 (3)	0.0246 (7)
H3	0.956411	0.62462	1.456512	0.03*
C4	0.8977 (6)	0.4937 (4)	1.3068 (3)	0.0229 (8)
O4	0.5459 (4)	0.3078 (2)	0.5468 (2)	0.0268 (6)
C5	0.8254 (5)	0.5053 (3)	1.1667 (3)	0.0219 (8)
C6	0.8057 (5)	0.3996 (4)	1.0852 (4)	0.0239 (8)
H6	0.841263	0.319649	1.125724	0.029*
C7	0.7402 (6)	0.3827 (4)	0.9458 (3)	0.0227 (8)
C8	0.6813 (5)	0.4844 (4)	0.8617 (4)	0.0225 (8)
H8	0.683558	0.5731	0.896017	0.027*
C9	0.6205 (6)	0.4570 (4)	0.7301 (3)	0.0235 (8)
H9	0.584027	0.527075	0.674937	0.028*
C10	0.6122 (5)	0.3264 (4)	0.6774 (3)	0.0222 (8)
C11	0.6740 (6)	0.2243 (3)	0.7582 (3)	0.0239 (8)
H11	0.672886	0.135839	0.723639	0.029*
C12	0.7371 (6)	0.2541 (4)	0.8900 (4)	0.0248 (8)
H12	0.780031	0.184357	0.944572	0.03*
C13	0.5448 (6)	0.1725 (4)	0.4953 (3)	0.0271 (8)
H13A	0.478172	0.113972	0.542081	0.033*
H13B	0.682686	0.144061	0.507724	0.033*
C14	0.4383 (6)	0.1602 (3)	0.3540 (4)	0.0257 (8)
C15	0.2362 (6)	0.1391 (4)	0.3169 (4)	0.0289 (9)
H15	0.163625	0.141814	0.379626	0.035*
C16	0.1380 (6)	0.1138 (4)	0.1878 (4)	0.0317 (9)
H16	−0.001294	0.097722	0.162886	0.038*
C17	0.2409 (7)	0.1119 (4)	0.0959 (4)	0.0342 (10)
H17	0.173166	0.09457	0.007728	0.041*
C18	0.4424 (7)	0.1353 (4)	0.1323 (4)	0.0361 (10)
H18	0.513831	0.134515	0.068935	0.043*
C19	0.5428 (7)	0.1602 (4)	0.2619 (4)	0.0333 (9)
H19	0.681933	0.177119	0.28672	0.04*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0348 (6)	0.0152 (5)	0.0244 (5)	−0.0036 (4)	0.0092 (4)	0.0061 (3)
S2	0.0427 (6)	0.0161 (5)	0.0327 (6)	−0.0047 (4)	0.0130 (4)	0.0029 (4)
O1	0.0447 (17)	0.0165 (13)	0.0277 (14)	−0.0001 (12)	0.0086 (12)	0.0057 (11)
C2	0.0270 (19)	0.0169 (17)	0.0257 (18)	−0.0019 (14)	0.0104 (15)	0.0078 (14)
N3	0.0353 (19)	0.0159 (15)	0.0228 (15)	−0.0019 (13)	0.0077 (13)	0.0037 (12)
C4	0.028 (2)	0.0178 (17)	0.0249 (18)	0.0003 (15)	0.0113 (15)	0.0032 (14)
O4	0.0428 (16)	0.0139 (12)	0.0228 (13)	−0.0028 (11)	0.0072 (11)	0.0036 (10)
C5	0.0239 (18)	0.0173 (17)	0.0268 (18)	−0.0029 (14)	0.0099 (14)	0.0056 (14)
C6	0.029 (2)	0.0167 (17)	0.0282 (19)	−0.0018 (15)	0.0102 (15)	0.0080 (14)
C7	0.027 (2)	0.0202 (18)	0.0226 (17)	−0.0011 (15)	0.0097 (14)	0.0055 (14)
C8	0.0269 (19)	0.0126 (16)	0.0301 (19)	−0.0019 (14)	0.0114 (15)	0.0009 (14)
C9	0.029 (2)	0.0172 (17)	0.0266 (19)	−0.0019 (15)	0.0109 (15)	0.0076 (14)
C10	0.0267 (19)	0.0192 (18)	0.0224 (18)	−0.0045 (14)	0.0096 (15)	0.0027 (14)
C11	0.031 (2)	0.0150 (17)	0.0262 (19)	−0.0022 (15)	0.0085 (15)	0.0028 (14)
C12	0.028 (2)	0.0197 (18)	0.0272 (19)	−0.0001 (15)	0.0068 (15)	0.0058 (15)
C13	0.039 (2)	0.0150 (17)	0.0257 (19)	−0.0001 (15)	0.0057 (16)	0.0006 (14)
C14	0.039 (2)	0.0111 (16)	0.0282 (19)	0.0012 (15)	0.0097 (16)	0.0053 (14)
C15	0.037 (2)	0.0191 (18)	0.031 (2)	0.0013 (16)	0.0110 (17)	0.0046 (15)
C16	0.038 (2)	0.0210 (19)	0.032 (2)	−0.0036 (17)	0.0012 (17)	0.0068 (16)
C17	0.057 (3)	0.0188 (19)	0.0227 (19)	−0.0092 (18)	0.0027 (18)	0.0070 (15)
C18	0.055 (3)	0.026 (2)	0.033 (2)	−0.0052 (19)	0.021 (2)	0.0074 (17)
C19	0.044 (3)	0.023 (2)	0.034 (2)	−0.0082 (18)	0.0131 (18)	0.0025 (16)

Geometric parameters (Å, º) top

S1—C2	1.741 (4)	C10—C11	1.395 (5)
S1—C5	1.752 (4)	C11—H11	0.95
S2—C2	1.639 (4)	C11—C12	1.388 (5)
O1—C4	1.227 (4)	C12—H12	0.95
C2—N3	1.363 (4)	C13—H13A	0.99
N3—H3	0.88	C13—H13B	0.99
N3—C4	1.375 (5)	C13—C14	1.508 (5)
C4—C5	1.478 (5)	C14—C15	1.375 (6)
O4—C10	1.365 (4)	C14—C19	1.384 (6)
O4—C13	1.448 (4)	C15—H15	0.95
C5—C6	1.327 (5)	C15—C16	1.388 (5)
C6—H6	0.95	C16—H16	0.95
C6—C7	1.452 (5)	C16—C17	1.374 (6)
C7—C8	1.411 (5)	C17—H17	0.95
C7—C12	1.400 (5)	C17—C18	1.374 (6)
C8—H8	0.95	C18—H18	0.95
C8—C9	1.382 (5)	C18—C19	1.397 (6)
C9—H9	0.95	C19—H19	0.95
C9—C10	1.403 (5)

C2—S1—C5	93.04 (17)	C12—C11—C10	118.9 (3)
S2—C2—S1	123.1 (2)	C12—C11—H11	120.5
N3—C2—S1	110.0 (3)	C7—C12—H12	118.6
N3—C2—S2	126.8 (3)	C11—C12—C7	122.8 (3)
C2—N3—H3	121.3	C11—C12—H12	118.6
C2—N3—C4	117.5 (3)	O4—C13—H13A	109.5
C4—N3—H3	121.3	O4—C13—H13B	109.5
O1—C4—N3	123.5 (3)	O4—C13—C14	110.6 (3)
O1—C4—C5	125.7 (3)	H13A—C13—H13B	108.1
N3—C4—C5	110.9 (3)	C14—C13—H13A	109.5
C10—O4—C13	115.3 (3)	C14—C13—H13B	109.5
C4—C5—S1	108.5 (3)	C15—C14—C13	119.3 (3)
C6—C5—S1	130.6 (3)	C15—C14—C19	119.7 (4)
C6—C5—C4	120.8 (3)	C19—C14—C13	120.8 (4)
C5—C6—H6	113.9	C14—C15—H15	119.9
C5—C6—C7	132.3 (3)	C14—C15—C16	120.2 (4)
C7—C6—H6	113.9	C16—C15—H15	119.9
C8—C7—C6	125.8 (3)	C15—C16—H16	119.8
C12—C7—C6	117.1 (3)	C17—C16—C15	120.5 (4)
C12—C7—C8	117.1 (3)	C17—C16—H16	119.8
C7—C8—H8	119.5	C16—C17—H17	120.2
C9—C8—C7	121.0 (3)	C18—C17—C16	119.6 (4)
C9—C8—H8	119.5	C18—C17—H17	120.2
C8—C9—H9	119.8	C17—C18—H18	119.8
C8—C9—C10	120.5 (3)	C17—C18—C19	120.4 (4)
C10—C9—H9	119.8	C19—C18—H18	119.8
O4—C10—C9	116.7 (3)	C14—C19—C18	119.6 (4)
O4—C10—C11	123.7 (3)	C14—C19—H19	120.2
C11—C10—C9	119.7 (3)	C18—C19—H19	120.2
C10—C11—H11	120.5

S1—C2—N3—C4	1.6 (4)	C6—C7—C12—C11	178.7 (3)
S1—C5—C6—C7	−1.2 (7)	C7—C8—C9—C10	1.3 (5)
S2—C2—N3—C4	−177.6 (3)	C8—C7—C12—C11	−1.9 (5)
O1—C4—C5—S1	178.5 (3)	C8—C9—C10—O4	178.4 (3)
O1—C4—C5—C6	−2.7 (6)	C8—C9—C10—C11	−2.8 (5)
C2—S1—C5—C4	2.1 (3)	C9—C10—C11—C12	1.9 (5)
C2—S1—C5—C6	−176.6 (4)	C10—O4—C13—C14	170.6 (3)
C2—N3—C4—O1	179.9 (4)	C10—C11—C12—C7	0.5 (6)
C2—N3—C4—C5	0.0 (5)	C12—C7—C8—C9	1.0 (5)
N3—C4—C5—S1	−1.6 (4)	C13—O4—C10—C9	178.2 (3)
N3—C4—C5—C6	177.2 (3)	C13—O4—C10—C11	−0.5 (5)
C4—C5—C6—C7	−179.7 (4)	C13—C14—C15—C16	−173.3 (3)
O4—C10—C11—C12	−179.4 (3)	C13—C14—C19—C18	173.6 (4)
O4—C13—C14—C15	−86.6 (4)	C14—C15—C16—C17	−1.2 (6)
O4—C13—C14—C19	98.1 (4)	C15—C14—C19—C18	−1.7 (6)
C5—S1—C2—S2	177.1 (3)	C15—C16—C17—C18	0.0 (6)
C5—S1—C2—N3	−2.2 (3)	C16—C17—C18—C19	0.3 (6)
C5—C6—C7—C8	0.8 (7)	C17—C18—C19—C14	0.5 (6)
C5—C6—C7—C12	−179.8 (4)	C19—C14—C15—C16	2.0 (5)
C6—C7—C8—C9	−179.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.94	2.810 (4)	169
C17—H17···S1ⁱⁱ	0.95	2.98	3.422 (4)	110

Symmetry codes: (i) −x+2, −y+1, −z+3; (ii) −x+1, −y+1, −z+1.

4-(5-(4-(Benzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)butanoic acid (4) top

Crystal data top

C₂₁H₁₉NO₄S₂	Z = 2
M_r = 413.49	F(000) = 432
Triclinic, P1	D_x = 1.425 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0919 (4) Å	Cell parameters from 4931 reflections
b = 7.3014 (4) Å	θ = 3.0–28.7°
c = 20.1260 (12) Å	µ = 0.31 mm⁻¹
α = 90.051 (5)°	T = 130 K
β = 93.744 (5)°	Plate, yellow
γ = 112.058 (6)°	0.49 × 0.40 × 0.07 mm
V = 963.43 (10) Å³

Data collection top

Rigaku SuperNova Dual source diffractometer with an Atlas detector	4501 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3575 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.3756 pixels mm^-1	θ_max = 28.7°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −9→9
T_min = 0.897, T_max = 0.981	l = −26→26
12987 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0271P)² + 1.7628P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
4501 reflections	Δρ_max = 0.38 e Å⁻³
254 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
C15	−0.5416 (4)	0.1330 (4)	0.34652 (14)	0.0237 (6)
H15	−0.563471	0.093816	0.391279	0.028*
C16	−0.7067 (4)	0.1142 (4)	0.30211 (15)	0.0279 (6)
H16	−0.840701	0.063562	0.316966	0.033*
C17	−0.6785 (4)	0.1684 (4)	0.23651 (15)	0.0279 (6)
H17	−0.792248	0.153078	0.206229	0.034*
C18	−0.4821 (5)	0.2455 (4)	0.21552 (15)	0.0284 (6)
H18	−0.460857	0.284009	0.17068	0.034*
C19	−0.3157 (4)	0.2666 (4)	0.26000 (14)	0.0260 (6)
H19	−0.181435	0.320778	0.245463	0.031*
C14	−0.3453 (4)	0.2085 (4)	0.32571 (13)	0.0203 (5)
C13	−0.1619 (4)	0.2201 (4)	0.37000 (13)	0.0213 (5)
H13A	−0.127662	0.103063	0.361379	0.026*
H13B	−0.043502	0.339715	0.359934	0.026*
O4	−0.2023 (3)	0.2276 (3)	0.43867 (9)	0.0223 (4)
C10	−0.0431 (4)	0.2479 (4)	0.48386 (13)	0.0194 (5)
C11	0.1494 (4)	0.2620 (4)	0.46717 (13)	0.0213 (5)
H11	0.175553	0.252439	0.421865	0.026*
C12	0.3018 (4)	0.2899 (4)	0.51696 (13)	0.0210 (5)
H12	0.432676	0.299554	0.505104	0.025*
C7	0.2699 (4)	0.3043 (4)	0.58428 (13)	0.0194 (5)
C8	0.0735 (4)	0.2877 (4)	0.60019 (13)	0.0216 (5)
H8	0.046221	0.29528	0.645485	0.026*
C9	−0.0792 (4)	0.2605 (4)	0.55092 (13)	0.0213 (5)
H9	−0.210411	0.250242	0.562541	0.026*
C6	0.4399 (4)	0.3355 (4)	0.63310 (13)	0.0198 (5)
H6	0.570351	0.384619	0.615615	0.024*
C5	0.4425 (4)	0.3061 (4)	0.69873 (13)	0.0193 (5)
C4	0.6366 (4)	0.3363 (4)	0.73803 (13)	0.0206 (5)
N3	0.5993 (3)	0.2715 (3)	0.80303 (11)	0.0211 (5)
C2	0.3988 (4)	0.1923 (4)	0.81760 (14)	0.0234 (6)
O1	0.8068 (3)	0.4047 (3)	0.71817 (10)	0.0261 (4)
C20	0.7713 (4)	0.2794 (4)	0.84963 (14)	0.0244 (6)
H20A	0.869889	0.243629	0.825217	0.029*
H20B	0.720119	0.180772	0.884476	0.029*
C21	0.8805 (4)	0.4836 (4)	0.88272 (14)	0.0249 (6)
H21A	0.915514	0.584321	0.847893	0.03*
H21B	1.009482	0.488859	0.906317	0.03*
C22	0.7508 (5)	0.5341 (4)	0.93241 (15)	0.0291 (6)
H22A	0.620211	0.526181	0.909348	0.035*
H22B	0.719536	0.436731	0.968307	0.035*
C23	0.8616 (5)	0.7380 (4)	0.96212 (14)	0.0270 (6)
O2	1.0192 (3)	0.7812 (3)	0.99848 (11)	0.0337 (5)
O3	0.7776 (3)	0.8651 (3)	0.94574 (11)	0.0345 (5)
H3	0.848534	0.97617	0.963322	0.052*
S1	0.23874 (10)	0.20742 (11)	0.74966 (3)	0.02378 (17)
S2	0.30627 (13)	0.09347 (13)	0.88742 (4)	0.0364 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C15	0.0221 (14)	0.0231 (14)	0.0265 (14)	0.0092 (11)	0.0012 (11)	−0.0007 (11)
C16	0.0182 (14)	0.0280 (15)	0.0378 (17)	0.0095 (12)	0.0002 (11)	−0.0040 (12)
C17	0.0259 (15)	0.0265 (15)	0.0339 (16)	0.0145 (12)	−0.0084 (12)	−0.0038 (12)
C18	0.0327 (16)	0.0268 (15)	0.0259 (15)	0.0123 (13)	−0.0020 (12)	0.0039 (11)
C19	0.0219 (14)	0.0256 (15)	0.0301 (15)	0.0082 (12)	0.0036 (11)	0.0050 (11)
C14	0.0191 (13)	0.0167 (12)	0.0255 (14)	0.0075 (10)	−0.0003 (10)	−0.0009 (10)
C13	0.0179 (13)	0.0234 (14)	0.0231 (13)	0.0084 (11)	0.0011 (10)	0.0012 (10)
O4	0.0175 (9)	0.0281 (10)	0.0228 (10)	0.0104 (8)	0.0006 (7)	0.0037 (8)
C10	0.0180 (13)	0.0147 (12)	0.0256 (14)	0.0066 (10)	−0.0003 (10)	0.0034 (10)
C11	0.0201 (13)	0.0223 (14)	0.0226 (13)	0.0090 (11)	0.0025 (10)	0.0035 (10)
C12	0.0159 (13)	0.0221 (13)	0.0265 (14)	0.0087 (11)	0.0029 (10)	0.0026 (10)
C7	0.0189 (13)	0.0144 (12)	0.0249 (13)	0.0063 (10)	0.0019 (10)	0.0029 (10)
C8	0.0262 (14)	0.0186 (13)	0.0221 (13)	0.0103 (11)	0.0055 (11)	0.0043 (10)
C9	0.0185 (13)	0.0210 (13)	0.0268 (14)	0.0096 (11)	0.0039 (10)	0.0043 (10)
C6	0.0140 (12)	0.0183 (13)	0.0277 (14)	0.0066 (10)	0.0028 (10)	0.0009 (10)
C5	0.0158 (12)	0.0176 (12)	0.0253 (13)	0.0073 (10)	0.0018 (10)	0.0000 (10)
C4	0.0202 (13)	0.0207 (13)	0.0228 (13)	0.0101 (11)	0.0001 (10)	−0.0011 (10)
N3	0.0194 (11)	0.0221 (12)	0.0231 (12)	0.0094 (9)	0.0003 (9)	0.0018 (9)
C2	0.0230 (14)	0.0215 (14)	0.0259 (14)	0.0086 (11)	0.0021 (11)	−0.0010 (11)
O1	0.0186 (10)	0.0307 (11)	0.0289 (11)	0.0090 (8)	0.0029 (8)	0.0021 (8)
C20	0.0235 (14)	0.0264 (15)	0.0249 (14)	0.0122 (12)	−0.0032 (11)	0.0005 (11)
C21	0.0231 (14)	0.0253 (15)	0.0251 (14)	0.0084 (12)	−0.0023 (11)	0.0005 (11)
C22	0.0279 (16)	0.0250 (15)	0.0314 (16)	0.0067 (12)	0.0007 (12)	−0.0002 (12)
C23	0.0307 (16)	0.0296 (15)	0.0223 (14)	0.0129 (13)	0.0032 (11)	0.0026 (11)
O2	0.0376 (13)	0.0294 (12)	0.0346 (12)	0.0153 (10)	−0.0108 (9)	−0.0017 (9)
O3	0.0397 (13)	0.0289 (12)	0.0364 (12)	0.0166 (10)	−0.0090 (10)	−0.0024 (9)
S1	0.0171 (3)	0.0277 (4)	0.0256 (4)	0.0073 (3)	0.0027 (2)	0.0015 (3)
S2	0.0334 (4)	0.0437 (5)	0.0266 (4)	0.0073 (4)	0.0078 (3)	0.0078 (3)

Geometric parameters (Å, º) top

C15—H15	0.95	C8—C9	1.376 (4)
C15—C16	1.390 (4)	C9—H9	0.95
C15—C14	1.385 (4)	C6—H6	0.95
C16—H16	0.95	C6—C5	1.338 (4)
C16—C17	1.384 (4)	C5—C4	1.483 (4)
C17—H17	0.95	C5—S1	1.752 (3)
C17—C18	1.387 (4)	C4—N3	1.399 (3)
C18—H18	0.95	C4—O1	1.215 (3)
C18—C19	1.394 (4)	N3—C2	1.371 (3)
C19—H19	0.95	N3—C20	1.473 (3)
C19—C14	1.394 (4)	C2—S1	1.750 (3)
C14—C13	1.503 (4)	C2—S2	1.641 (3)
C13—H13A	0.99	C20—H20A	0.99
C13—H13B	0.99	C20—H20B	0.99
C13—O4	1.435 (3)	C20—C21	1.526 (4)
O4—C10	1.365 (3)	C21—H21A	0.99
C10—C11	1.393 (4)	C21—H21B	0.99
C10—C9	1.399 (4)	C21—C22	1.535 (4)
C11—H11	0.95	C22—H22A	0.99
C11—C12	1.381 (4)	C22—H22B	0.99
C12—H12	0.95	C22—C23	1.500 (4)
C12—C7	1.398 (4)	C23—O2	1.230 (3)
C7—C8	1.410 (4)	C23—O3	1.310 (3)
C7—C6	1.453 (4)	O3—H3	0.84
C8—H8	0.95

C16—C15—H15	119.9	C8—C9—C10	120.7 (2)
C14—C15—H15	119.9	C8—C9—H9	119.7
C14—C15—C16	120.2 (3)	C7—C6—H6	114.8
C15—C16—H16	119.6	C5—C6—C7	130.5 (2)
C17—C16—C15	120.9 (3)	C5—C6—H6	114.8
C17—C16—H16	119.6	C6—C5—C4	120.7 (2)
C16—C17—H17	120.4	C6—C5—S1	129.6 (2)
C16—C17—C18	119.2 (3)	C4—C5—S1	109.39 (19)
C18—C17—H17	120.4	N3—C4—C5	110.6 (2)
C17—C18—H18	119.9	O1—C4—C5	126.5 (2)
C17—C18—C19	120.2 (3)	O1—C4—N3	123.0 (2)
C19—C18—H18	119.9	C4—N3—C20	119.4 (2)
C18—C19—H19	119.8	C2—N3—C4	116.3 (2)
C18—C19—C14	120.4 (3)	C2—N3—C20	124.1 (2)
C14—C19—H19	119.8	N3—C2—S1	110.90 (19)
C15—C14—C19	119.2 (3)	N3—C2—S2	127.8 (2)
C15—C14—C13	122.7 (2)	S2—C2—S1	121.31 (17)
C19—C14—C13	118.0 (2)	N3—C20—H20A	109.1
C14—C13—H13A	109.6	N3—C20—H20B	109.1
C14—C13—H13B	109.6	N3—C20—C21	112.3 (2)
H13A—C13—H13B	108.1	H20A—C20—H20B	107.9
O4—C13—C14	110.2 (2)	C21—C20—H20A	109.1
O4—C13—H13A	109.6	C21—C20—H20B	109.1
O4—C13—H13B	109.6	C20—C21—H21A	109.1
C10—O4—C13	115.7 (2)	C20—C21—H21B	109.1
O4—C10—C11	124.4 (2)	C20—C21—C22	112.6 (2)
O4—C10—C9	116.2 (2)	H21A—C21—H21B	107.8
C11—C10—C9	119.4 (2)	C22—C21—H21A	109.1
C10—C11—H11	120.2	C22—C21—H21B	109.1
C12—C11—C10	119.5 (2)	C21—C22—H22A	109.5
C12—C11—H11	120.2	C21—C22—H22B	109.5
C11—C12—H12	118.9	H22A—C22—H22B	108.1
C11—C12—C7	122.1 (2)	C23—C22—C21	110.7 (2)
C7—C12—H12	118.9	C23—C22—H22A	109.5
C12—C7—C8	117.5 (2)	C23—C22—H22B	109.5
C12—C7—C6	118.2 (2)	O2—C23—C22	122.3 (3)
C8—C7—C6	124.3 (2)	O2—C23—O3	123.2 (3)
C7—C8—H8	119.6	O3—C23—C22	114.5 (3)
C9—C8—C7	120.8 (2)	C23—O3—H3	109.5
C9—C8—H8	119.6	C2—S1—C5	92.66 (13)
C10—C9—H9	119.7

C15—C16—C17—C18	−1.1 (4)	C9—C10—C11—C12	−0.6 (4)
C15—C14—C13—O4	−25.0 (4)	C6—C7—C8—C9	179.2 (2)
C16—C15—C14—C19	0.5 (4)	C6—C5—C4—N3	−171.9 (2)
C16—C15—C14—C13	−175.9 (3)	C6—C5—C4—O1	7.1 (4)
C16—C17—C18—C19	0.4 (4)	C6—C5—S1—C2	169.8 (3)
C17—C18—C19—C14	0.7 (4)	C5—C4—N3—C2	1.1 (3)
C18—C19—C14—C15	−1.1 (4)	C5—C4—N3—C20	177.1 (2)
C18—C19—C14—C13	175.4 (3)	C4—C5—S1—C2	−3.3 (2)
C19—C14—C13—O4	158.6 (2)	C4—N3—C2—S1	−3.6 (3)
C14—C15—C16—C17	0.7 (4)	C4—N3—C2—S2	176.4 (2)
C14—C13—O4—C10	−177.0 (2)	C4—N3—C20—C21	83.1 (3)
C13—O4—C10—C11	0.3 (4)	N3—C2—S1—C5	3.9 (2)
C13—O4—C10—C9	178.4 (2)	N3—C20—C21—C22	69.9 (3)
O4—C10—C11—C12	177.5 (2)	C2—N3—C20—C21	−101.2 (3)
O4—C10—C9—C8	−177.9 (2)	O1—C4—N3—C2	−178.0 (3)
C10—C11—C12—C7	0.1 (4)	O1—C4—N3—C20	−2.0 (4)
C11—C10—C9—C8	0.4 (4)	C20—N3—C2—S1	−179.39 (19)
C11—C12—C7—C8	0.5 (4)	C20—N3—C2—S2	0.6 (4)
C11—C12—C7—C6	−179.4 (2)	C20—C21—C22—C23	−178.3 (2)
C12—C7—C8—C9	−0.7 (4)	C21—C22—C23—O2	−65.8 (4)
C12—C7—C6—C5	−161.1 (3)	C21—C22—C23—O3	113.7 (3)
C7—C8—C9—C10	0.3 (4)	S1—C5—C4—N3	1.9 (3)
C7—C6—C5—C4	175.8 (3)	S1—C5—C4—O1	−179.0 (2)
C7—C6—C5—S1	3.4 (4)	S2—C2—S1—C5	−176.08 (18)
C8—C7—C6—C5	18.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.81	2.645 (3)	175
C13—H13B···O1ⁱⁱ	0.99	2.6	3.522 (3)	155
C13—H13A···S1ⁱⁱⁱ	0.99	3.03	3.792 (3)	135

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

5-(4-(Diphenylamino)benzylidene)-2-thioxothiazolidin-4-one (5) top

Crystal data top

C₂₂H₁₆N₂OS₂	Z = 4
M_r = 388.49	F(000) = 808
Triclinic, P1	D_x = 1.348 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.5325 (5) Å	Cell parameters from 8383 reflections
b = 12.8492 (6) Å	θ = 3.2–28.6°
c = 13.6465 (7) Å	µ = 0.29 mm⁻¹
α = 96.342 (4)°	T = 130 K
β = 92.497 (4)°	Irregular, red
γ = 118.148 (4)°	0.50 × 0.25 × 0.18 mm
V = 1914.26 (17) Å³

Data collection top

Rigaku SuperNova Dual source diffractometer with an Atlas detector	8981 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	6679 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.3756 pixels mm^-1	θ_max = 28.7°, θ_min = 3.0°
ω scans	h = −16→16
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −17→17
T_min = 0.456, T_max = 1	l = −18→18
25766 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.0505P)² + 3.5362P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
8981 reflections	Δρ_max = 0.47 e Å⁻³
487 parameters	Δρ_min = −0.35 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C2D	0.2202 (2)	0.5767 (3)	0.6587 (2)	0.0263 (6)
N3D	0.2167 (2)	0.5261 (2)	0.56519 (17)	0.0248 (5)
H3D	0.283327	0.548945	0.535312	0.03*
C4D	0.1058 (2)	0.4379 (3)	0.5182 (2)	0.0243 (6)
C5D	0.0094 (2)	0.4180 (3)	0.5835 (2)	0.0235 (6)
O1D	0.09290 (17)	0.38515 (18)	0.43481 (15)	0.0278 (4)
C6D	−0.1064 (2)	0.3335 (2)	0.5537 (2)	0.0239 (6)
H6D	−0.118837	0.295431	0.48732	0.029*
C7D	−0.2151 (2)	0.2900 (3)	0.6037 (2)	0.0238 (6)
C12D	−0.3220 (3)	0.1927 (3)	0.5529 (2)	0.0266 (6)
H12D	−0.320568	0.161846	0.486717	0.032*
C11D	−0.4280 (3)	0.1415 (3)	0.5961 (2)	0.0268 (6)
H11D	−0.498303	0.075978	0.559541	0.032*
C10D	−0.4343 (2)	0.1843 (2)	0.6937 (2)	0.0235 (6)
C9D	−0.3292 (2)	0.2841 (3)	0.7446 (2)	0.0254 (6)
H9D	−0.331531	0.316747	0.809967	0.03*
C8D	−0.2226 (2)	0.3347 (3)	0.6999 (2)	0.0246 (6)
H8D	−0.152721	0.401597	0.735531	0.029*
N1D	−0.5400 (2)	0.1299 (2)	0.73885 (17)	0.0264 (5)
C19D	−0.5430 (2)	0.1542 (3)	0.8434 (2)	0.0255 (6)
C24D	−0.6266 (3)	0.1896 (3)	0.8755 (2)	0.0312 (7)
H24D	−0.677243	0.200326	0.828368	0.037*
C23D	−0.6360 (3)	0.2091 (3)	0.9758 (2)	0.0375 (7)
H23D	−0.693618	0.232398	0.997392	0.045*
C22D	−0.5620 (3)	0.1947 (3)	1.0440 (2)	0.0418 (8)
H22D	−0.56751	0.209556	1.112882	0.05*
C21D	−0.4793 (3)	0.1584 (3)	1.0125 (2)	0.0424 (8)
H21D	−0.429155	0.147262	1.059848	0.051*
C20D	−0.4696 (3)	0.1385 (3)	0.9121 (2)	0.0340 (7)
H20D	−0.412619	0.114143	0.890667	0.041*
C13D	−0.6560 (2)	0.0516 (3)	0.6829 (2)	0.0258 (6)
C18D	−0.6963 (3)	0.0843 (3)	0.6012 (2)	0.0283 (6)
H18D	−0.644607	0.156411	0.57742	0.034*
C17D	−0.8139 (3)	0.0094 (3)	0.5547 (2)	0.0323 (7)
H17D	−0.842355	0.030261	0.498379	0.039*
C16D	−0.8893 (3)	−0.0951 (3)	0.5900 (2)	0.0321 (7)
H16D	−0.970074	−0.144246	0.559133	0.039*
C15D	−0.8480 (3)	−0.1280 (3)	0.6695 (2)	0.0337 (7)
H15D	−0.899916	−0.199828	0.693622	0.04*
C14D	−0.7299 (3)	−0.0557 (3)	0.7146 (2)	0.0310 (7)
H14D	−0.699839	−0.080283	0.767492	0.037*
C2E	0.2852 (3)	0.4244 (3)	0.2151 (2)	0.0323 (7)
N3E	0.2866 (2)	0.4495 (2)	0.31424 (18)	0.0286 (5)
H3E	0.218375	0.424134	0.342035	0.034*
C4E	0.3981 (2)	0.5159 (3)	0.3707 (2)	0.0256 (6)
C5E	0.4966 (3)	0.5408 (3)	0.3068 (2)	0.0266 (6)
O1E	0.41003 (18)	0.5491 (2)	0.45980 (16)	0.0341 (5)
C6E	0.6128 (3)	0.6054 (3)	0.3471 (2)	0.0263 (6)
H6E	0.621704	0.622394	0.417454	0.032*
C7E	0.7268 (2)	0.6541 (3)	0.3045 (2)	0.0252 (6)
C12E	0.8312 (3)	0.7363 (3)	0.3675 (2)	0.0261 (6)
H12E	0.824907	0.750189	0.436311	0.031*
C11E	0.9422 (3)	0.7975 (3)	0.3330 (2)	0.0276 (6)
H11E	1.011418	0.85181	0.3778	0.033*
C10E	0.9534 (3)	0.7801 (3)	0.2317 (2)	0.0265 (6)
C9E	0.8512 (3)	0.6942 (3)	0.1683 (2)	0.0285 (6)
H9E	0.858381	0.678123	0.099942	0.034*
C8E	0.7399 (3)	0.6324 (3)	0.2044 (2)	0.0279 (6)
H8E	0.671577	0.574586	0.160363	0.033*
N1E	1.0654 (2)	0.8479 (2)	0.19763 (19)	0.0303 (6)
C19E	1.0953 (3)	0.8144 (3)	0.1044 (2)	0.0313 (7)
C20E	1.0814 (3)	0.7019 (3)	0.0774 (2)	0.0360 (7)
H20E	1.048787	0.643762	0.120659	0.043*
C21E	1.1152 (3)	0.6735 (3)	−0.0131 (3)	0.0432 (9)
H21E	1.104899	0.595658	−0.03228	0.052*
C22E	1.1640 (3)	0.7588 (4)	−0.0750 (3)	0.0513 (10)
H22E	1.188181	0.740057	−0.136587	0.062*
C23E	1.1774 (4)	0.8705 (4)	−0.0476 (3)	0.0582 (11)
H23E	1.210223	0.9286	−0.090763	0.07*
C24E	1.1439 (3)	0.8993 (3)	0.0415 (3)	0.0466 (9)
H24E	1.154025	0.977158	0.059971	0.056*
C13E	1.1495 (3)	0.9622 (3)	0.2516 (2)	0.0294 (6)
C18E	1.1156 (3)	1.0487 (3)	0.2772 (3)	0.0362 (7)
H18E	1.033988	1.031673	0.260578	0.043*
C17E	1.1993 (3)	1.1594 (3)	0.3267 (3)	0.0444 (9)
H17E	1.175194	1.218356	0.343955	0.053*
C16E	1.3193 (3)	1.1853 (3)	0.3515 (3)	0.0442 (9)
H16E	1.377249	1.261706	0.385318	0.053*
C15E	1.3530 (3)	1.0988 (3)	0.3263 (3)	0.0416 (8)
H15E	1.434599	1.115879	0.342975	0.05*
C14E	1.2692 (3)	0.9876 (3)	0.2770 (2)	0.0342 (7)
H14E	1.293125	0.928432	0.26047	0.041*
S1D	0.07352 (6)	0.51434 (7)	0.69619 (5)	0.02786 (17)
S2D	0.34175 (7)	0.67997 (8)	0.72782 (6)	0.0394 (2)
S1E	0.43463 (7)	0.48156 (8)	0.18354 (6)	0.0338 (2)
S2E	0.16332 (8)	0.35314 (10)	0.13556 (7)	0.0501 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2D	0.0182 (13)	0.0292 (15)	0.0302 (15)	0.0098 (11)	0.0048 (11)	0.0060 (12)
N3D	0.0151 (11)	0.0299 (13)	0.0269 (12)	0.0085 (10)	0.0062 (9)	0.0039 (10)
C4D	0.0172 (13)	0.0267 (14)	0.0298 (14)	0.0105 (11)	0.0054 (11)	0.0067 (12)
C5D	0.0180 (13)	0.0275 (14)	0.0261 (14)	0.0114 (11)	0.0057 (11)	0.0041 (11)
O1D	0.0186 (9)	0.0327 (11)	0.0288 (11)	0.0101 (8)	0.0056 (8)	0.0012 (9)
C6D	0.0203 (13)	0.0254 (14)	0.0270 (14)	0.0114 (11)	0.0059 (11)	0.0043 (11)
C7D	0.0152 (12)	0.0267 (14)	0.0289 (14)	0.0095 (11)	0.0038 (11)	0.0045 (11)
C12D	0.0226 (14)	0.0309 (15)	0.0243 (14)	0.0121 (12)	0.0040 (11)	−0.0005 (12)
C11D	0.0188 (13)	0.0284 (15)	0.0279 (14)	0.0080 (11)	0.0027 (11)	−0.0002 (12)
C10D	0.0180 (13)	0.0261 (14)	0.0268 (14)	0.0103 (11)	0.0054 (11)	0.0064 (11)
C9D	0.0217 (13)	0.0273 (14)	0.0258 (14)	0.0111 (12)	0.0038 (11)	0.0009 (11)
C8D	0.0185 (13)	0.0252 (14)	0.0261 (14)	0.0076 (11)	0.0029 (11)	0.0020 (11)
N1D	0.0173 (11)	0.0326 (13)	0.0249 (12)	0.0084 (10)	0.0045 (9)	0.0031 (10)
C19D	0.0184 (13)	0.0271 (14)	0.0248 (14)	0.0059 (11)	0.0053 (11)	0.0034 (11)
C24D	0.0292 (15)	0.0347 (16)	0.0309 (15)	0.0167 (13)	0.0039 (12)	0.0030 (13)
C23D	0.0346 (17)	0.0440 (19)	0.0350 (17)	0.0204 (15)	0.0093 (14)	0.0001 (14)
C22D	0.0388 (18)	0.054 (2)	0.0251 (15)	0.0175 (17)	0.0087 (14)	−0.0001 (15)
C21D	0.0355 (18)	0.059 (2)	0.0306 (17)	0.0216 (17)	0.0003 (14)	0.0075 (16)
C20D	0.0251 (15)	0.0453 (19)	0.0341 (16)	0.0181 (14)	0.0067 (13)	0.0079 (14)
C13D	0.0171 (13)	0.0305 (15)	0.0263 (14)	0.0096 (11)	0.0050 (11)	−0.0015 (12)
C18D	0.0235 (14)	0.0292 (15)	0.0309 (15)	0.0119 (12)	0.0038 (12)	0.0026 (12)
C17D	0.0274 (15)	0.0358 (17)	0.0351 (16)	0.0179 (13)	−0.0001 (13)	−0.0012 (13)
C16D	0.0200 (14)	0.0354 (17)	0.0341 (16)	0.0100 (13)	0.0014 (12)	−0.0057 (13)
C15D	0.0259 (15)	0.0317 (16)	0.0331 (16)	0.0058 (13)	0.0081 (13)	0.0016 (13)
C14D	0.0280 (15)	0.0358 (17)	0.0242 (14)	0.0111 (13)	0.0064 (12)	0.0032 (12)
C2E	0.0238 (15)	0.0334 (16)	0.0374 (17)	0.0120 (13)	0.0059 (12)	0.0034 (13)
N3E	0.0175 (11)	0.0323 (13)	0.0339 (13)	0.0103 (10)	0.0082 (10)	0.0035 (11)
C4E	0.0194 (13)	0.0291 (15)	0.0322 (15)	0.0135 (12)	0.0073 (11)	0.0087 (12)
C5E	0.0233 (14)	0.0318 (15)	0.0277 (14)	0.0147 (12)	0.0092 (11)	0.0065 (12)
O1E	0.0213 (10)	0.0503 (14)	0.0297 (11)	0.0162 (10)	0.0077 (9)	0.0045 (10)
C6E	0.0249 (14)	0.0334 (15)	0.0255 (14)	0.0167 (12)	0.0088 (11)	0.0078 (12)
C7E	0.0195 (13)	0.0277 (14)	0.0299 (14)	0.0117 (11)	0.0065 (11)	0.0069 (12)
C12E	0.0239 (14)	0.0310 (15)	0.0259 (14)	0.0143 (12)	0.0078 (11)	0.0059 (12)
C11E	0.0192 (13)	0.0306 (15)	0.0310 (15)	0.0102 (12)	0.0035 (11)	0.0044 (12)
C10E	0.0220 (14)	0.0315 (15)	0.0293 (15)	0.0143 (12)	0.0076 (11)	0.0087 (12)
C9E	0.0236 (14)	0.0380 (17)	0.0255 (14)	0.0158 (13)	0.0053 (11)	0.0047 (12)
C8E	0.0211 (14)	0.0320 (15)	0.0302 (15)	0.0128 (12)	0.0018 (11)	0.0034 (12)
N1E	0.0227 (12)	0.0335 (14)	0.0315 (13)	0.0105 (11)	0.0096 (10)	0.0041 (11)
C19E	0.0194 (14)	0.0406 (17)	0.0306 (15)	0.0120 (13)	0.0055 (12)	0.0028 (13)
C20E	0.0259 (15)	0.0463 (19)	0.0344 (17)	0.0175 (14)	0.0016 (13)	0.0000 (14)
C21E	0.0276 (17)	0.051 (2)	0.045 (2)	0.0173 (16)	0.0010 (14)	−0.0099 (16)
C22E	0.0322 (18)	0.064 (3)	0.041 (2)	0.0113 (18)	0.0161 (15)	−0.0055 (18)
C23E	0.056 (2)	0.058 (3)	0.040 (2)	0.010 (2)	0.0202 (18)	0.0065 (19)
C24E	0.047 (2)	0.043 (2)	0.0411 (19)	0.0142 (17)	0.0156 (16)	0.0071 (16)
C13E	0.0266 (15)	0.0297 (15)	0.0304 (15)	0.0111 (12)	0.0104 (12)	0.0071 (12)
C18E	0.0327 (17)	0.0374 (18)	0.0435 (19)	0.0196 (14)	0.0123 (14)	0.0090 (15)
C17E	0.048 (2)	0.0304 (17)	0.055 (2)	0.0168 (16)	0.0197 (17)	0.0110 (16)
C16E	0.043 (2)	0.0298 (17)	0.0432 (19)	0.0030 (15)	0.0112 (16)	0.0051 (15)
C15E	0.0268 (16)	0.0427 (19)	0.0428 (19)	0.0058 (14)	0.0056 (14)	0.0096 (16)
C14E	0.0265 (15)	0.0375 (17)	0.0407 (18)	0.0156 (14)	0.0107 (13)	0.0101 (14)
S1D	0.0186 (3)	0.0335 (4)	0.0268 (4)	0.0094 (3)	0.0047 (3)	0.0000 (3)
S2D	0.0209 (4)	0.0441 (5)	0.0387 (4)	0.0070 (3)	0.0016 (3)	−0.0088 (4)
S1E	0.0223 (4)	0.0436 (5)	0.0298 (4)	0.0119 (3)	0.0066 (3)	0.0003 (3)
S2E	0.0250 (4)	0.0709 (7)	0.0384 (5)	0.0133 (4)	−0.0004 (3)	−0.0058 (4)

Geometric parameters (Å, º) top

C2D—N3D	1.355 (4)	C2E—N3E	1.353 (4)
C2D—S2D	1.632 (3)	C2E—S2E	1.632 (3)
C2D—S1D	1.751 (3)	C2E—S1E	1.754 (3)
N3D—C4D	1.380 (3)	N3E—C4E	1.382 (4)
N3D—H3D	0.88	N3E—H3E	0.88
C4D—O1D	1.221 (3)	C4E—O1E	1.221 (3)
C4D—C5D	1.473 (4)	C4E—C5E	1.473 (4)
C5D—C6D	1.347 (4)	C5E—C6E	1.342 (4)
C5D—S1D	1.754 (3)	C5E—S1E	1.749 (3)
C6D—C7D	1.442 (4)	C6E—C7E	1.442 (4)
C6D—H6D	0.95	C6E—H6E	0.95
C7D—C8D	1.400 (4)	C7E—C8E	1.397 (4)
C7D—C12D	1.409 (4)	C7E—C12E	1.402 (4)
C12D—C11D	1.369 (4)	C12E—C11E	1.372 (4)
C12D—H12D	0.95	C12E—H12E	0.95
C11D—C10D	1.403 (4)	C11E—C10E	1.399 (4)
C11D—H11D	0.95	C11E—H11E	0.95
C10D—N1D	1.384 (3)	C10E—N1E	1.393 (4)
C10D—C9D	1.412 (4)	C10E—C9E	1.402 (4)
C9D—C8D	1.385 (4)	C9E—C8E	1.385 (4)
C9D—H9D	0.95	C9E—H9E	0.95
C8D—H8D	0.95	C8E—H8E	0.95
N1D—C19D	1.433 (4)	N1E—C19E	1.420 (4)
N1D—C13D	1.436 (4)	N1E—C13E	1.430 (4)
C19D—C20D	1.381 (4)	C19E—C20E	1.377 (5)
C19D—C24D	1.392 (4)	C19E—C24E	1.387 (5)
C24D—C23D	1.385 (4)	C20E—C21E	1.389 (5)
C24D—H24D	0.95	C20E—H20E	0.95
C23D—C22D	1.373 (5)	C21E—C22E	1.381 (6)
C23D—H23D	0.95	C21E—H21E	0.95
C22D—C21D	1.389 (5)	C22E—C23E	1.369 (6)
C22D—H22D	0.95	C22E—H22E	0.95
C21D—C20D	1.387 (4)	C23E—C24E	1.372 (5)
C21D—H21D	0.95	C23E—H23E	0.95
C20D—H20D	0.95	C24E—H24E	0.95
C13D—C14D	1.381 (4)	C13E—C18E	1.382 (4)
C13D—C18D	1.389 (4)	C13E—C14E	1.395 (4)
C18D—C17D	1.395 (4)	C18E—C17E	1.378 (5)
C18D—H18D	0.95	C18E—H18E	0.95
C17D—C16D	1.383 (5)	C17E—C16E	1.395 (5)
C17D—H17D	0.95	C17E—H17E	0.95
C16D—C15D	1.372 (5)	C16E—C15E	1.379 (5)
C16D—H16D	0.95	C16E—H16E	0.95
C15D—C14D	1.388 (4)	C15E—C14E	1.380 (5)
C15D—H15D	0.95	C15E—H15E	0.95
C14D—H14D	0.95	C14E—H14E	0.95

N3D—C2D—S2D	125.9 (2)	N3E—C2E—S1E	109.9 (2)
N3D—C2D—S1D	110.0 (2)	S2E—C2E—S1E	124.54 (19)
S2D—C2D—S1D	124.14 (18)	C2E—N3E—C4E	118.3 (2)
C2D—N3D—C4D	118.1 (2)	C2E—N3E—H3E	120.9
C2D—N3D—H3D	120.9	C4E—N3E—H3E	120.9
C4D—N3D—H3D	120.9	O1E—C4E—N3E	123.8 (2)
O1D—C4D—N3D	123.4 (2)	O1E—C4E—C5E	126.6 (3)
O1D—C4D—C5D	126.5 (3)	N3E—C4E—C5E	109.6 (2)
N3D—C4D—C5D	110.1 (2)	C6E—C5E—C4E	119.3 (3)
C6D—C5D—C4D	120.4 (3)	C6E—C5E—S1E	130.9 (2)
C6D—C5D—S1D	130.2 (2)	C4E—C5E—S1E	109.8 (2)
C4D—C5D—S1D	109.4 (2)	C5E—C6E—C7E	132.5 (3)
C5D—C6D—C7D	132.1 (3)	C5E—C6E—H6E	113.7
C5D—C6D—H6D	113.9	C7E—C6E—H6E	113.7
C7D—C6D—H6D	113.9	C8E—C7E—C12E	117.6 (3)
C8D—C7D—C12D	117.0 (2)	C8E—C7E—C6E	125.2 (3)
C8D—C7D—C6D	125.3 (3)	C12E—C7E—C6E	117.1 (3)
C12D—C7D—C6D	117.7 (3)	C11E—C12E—C7E	122.1 (3)
C11D—C12D—C7D	121.9 (3)	C11E—C12E—H12E	118.9
C11D—C12D—H12D	119	C7E—C12E—H12E	118.9
C7D—C12D—H12D	119	C12E—C11E—C10E	120.0 (3)
C12D—C11D—C10D	120.9 (3)	C12E—C11E—H11E	120
C12D—C11D—H11D	119.5	C10E—C11E—H11E	120
C10D—C11D—H11D	119.5	N1E—C10E—C11E	119.0 (3)
N1D—C10D—C11D	121.1 (2)	N1E—C10E—C9E	122.4 (3)
N1D—C10D—C9D	121.0 (2)	C11E—C10E—C9E	118.6 (3)
C11D—C10D—C9D	117.9 (2)	C8E—C9E—C10E	120.6 (3)
C8D—C9D—C10D	120.3 (3)	C8E—C9E—H9E	119.7
C8D—C9D—H9D	119.8	C10E—C9E—H9E	119.7
C10D—C9D—H9D	119.8	C9E—C8E—C7E	120.9 (3)
C9D—C8D—C7D	121.8 (3)	C9E—C8E—H8E	119.5
C9D—C8D—H8D	119.1	C7E—C8E—H8E	119.5
C7D—C8D—H8D	119.1	C10E—N1E—C19E	122.4 (3)
C10D—N1D—C19D	122.5 (2)	C10E—N1E—C13E	119.9 (2)
C10D—N1D—C13D	122.0 (2)	C19E—N1E—C13E	117.3 (2)
C19D—N1D—C13D	115.3 (2)	C20E—C19E—C24E	119.9 (3)
C20D—C19D—C24D	119.7 (3)	C20E—C19E—N1E	121.4 (3)
C20D—C19D—N1D	121.9 (3)	C24E—C19E—N1E	118.6 (3)
C24D—C19D—N1D	118.3 (3)	C19E—C20E—C21E	119.8 (3)
C23D—C24D—C19D	120.2 (3)	C19E—C20E—H20E	120.1
C23D—C24D—H24D	119.9	C21E—C20E—H20E	120.1
C19D—C24D—H24D	119.9	C22E—C21E—C20E	119.8 (4)
C22D—C23D—C24D	120.0 (3)	C22E—C21E—H21E	120.1
C22D—C23D—H23D	120	C20E—C21E—H21E	120.1
C24D—C23D—H23D	120	C23E—C22E—C21E	119.9 (3)
C23D—C22D—C21D	120.1 (3)	C23E—C22E—H22E	120
C23D—C22D—H22D	120	C21E—C22E—H22E	120
C21D—C22D—H22D	120	C22E—C23E—C24E	120.7 (4)
C20D—C21D—C22D	120.2 (3)	C22E—C23E—H23E	119.6
C20D—C21D—H21D	119.9	C24E—C23E—H23E	119.6
C22D—C21D—H21D	119.9	C23E—C24E—C19E	119.8 (4)
C19D—C20D—C21D	119.8 (3)	C23E—C24E—H24E	120.1
C19D—C20D—H20D	120.1	C19E—C24E—H24E	120.1
C21D—C20D—H20D	120.1	C18E—C13E—C14E	119.4 (3)
C14D—C13D—C18D	120.1 (3)	C18E—C13E—N1E	121.6 (3)
C14D—C13D—N1D	118.6 (3)	C14E—C13E—N1E	119.0 (3)
C18D—C13D—N1D	121.3 (3)	C17E—C18E—C13E	120.4 (3)
C13D—C18D—C17D	118.9 (3)	C17E—C18E—H18E	119.8
C13D—C18D—H18D	120.6	C13E—C18E—H18E	119.8
C17D—C18D—H18D	120.6	C18E—C17E—C16E	120.2 (3)
C16D—C17D—C18D	120.5 (3)	C18E—C17E—H17E	119.9
C16D—C17D—H17D	119.8	C16E—C17E—H17E	119.9
C18D—C17D—H17D	119.8	C15E—C16E—C17E	119.3 (3)
C15D—C16D—C17D	120.3 (3)	C15E—C16E—H16E	120.3
C15D—C16D—H16D	119.8	C17E—C16E—H16E	120.3
C17D—C16D—H16D	119.8	C16E—C15E—C14E	120.6 (3)
C16D—C15D—C14D	119.6 (3)	C16E—C15E—H15E	119.7
C16D—C15D—H15D	120.2	C14E—C15E—H15E	119.7
C14D—C15D—H15D	120.2	C15E—C14E—C13E	120.0 (3)
C13D—C14D—C15D	120.4 (3)	C15E—C14E—H14E	120
C13D—C14D—H14D	119.8	C13E—C14E—H14E	120
C15D—C14D—H14D	119.8	C2D—S1D—C5D	92.48 (13)
N3E—C2E—S2E	125.6 (2)	C5E—S1E—C2E	92.34 (14)

S2D—C2D—N3D—C4D	178.7 (2)	O1E—C4E—C5E—C6E	0.5 (5)
S1D—C2D—N3D—C4D	−1.1 (3)	N3E—C4E—C5E—C6E	179.5 (3)
C2D—N3D—C4D—O1D	−178.6 (3)	O1E—C4E—C5E—S1E	−176.7 (3)
C2D—N3D—C4D—C5D	0.8 (4)	N3E—C4E—C5E—S1E	2.2 (3)
O1D—C4D—C5D—C6D	1.0 (5)	C4E—C5E—C6E—C7E	−173.0 (3)
N3D—C4D—C5D—C6D	−178.4 (3)	S1E—C5E—C6E—C7E	3.6 (5)
O1D—C4D—C5D—S1D	179.2 (3)	C5E—C6E—C7E—C8E	−6.6 (5)
N3D—C4D—C5D—S1D	−0.2 (3)	C5E—C6E—C7E—C12E	168.5 (3)
C4D—C5D—C6D—C7D	175.1 (3)	C8E—C7E—C12E—C11E	2.3 (4)
S1D—C5D—C6D—C7D	−2.7 (5)	C6E—C7E—C12E—C11E	−173.1 (3)
C5D—C6D—C7D—C8D	3.1 (5)	C7E—C12E—C11E—C10E	1.0 (5)
C5D—C6D—C7D—C12D	−175.3 (3)	C12E—C11E—C10E—N1E	176.6 (3)
C8D—C7D—C12D—C11D	−1.9 (4)	C12E—C11E—C10E—C9E	−3.8 (4)
C6D—C7D—C12D—C11D	176.7 (3)	N1E—C10E—C9E—C8E	−177.0 (3)
C7D—C12D—C11D—C10D	0.1 (5)	C11E—C10E—C9E—C8E	3.4 (4)
C12D—C11D—C10D—N1D	−177.5 (3)	C10E—C9E—C8E—C7E	−0.1 (5)
C12D—C11D—C10D—C9D	1.9 (4)	C12E—C7E—C8E—C9E	−2.7 (4)
N1D—C10D—C9D—C8D	177.4 (3)	C6E—C7E—C8E—C9E	172.3 (3)
C11D—C10D—C9D—C8D	−2.1 (4)	C11E—C10E—N1E—C19E	161.6 (3)
C10D—C9D—C8D—C7D	0.3 (4)	C9E—C10E—N1E—C19E	−18.0 (4)
C12D—C7D—C8D—C9D	1.7 (4)	C11E—C10E—N1E—C13E	−25.7 (4)
C6D—C7D—C8D—C9D	−176.7 (3)	C9E—C10E—N1E—C13E	154.7 (3)
C11D—C10D—N1D—C19D	166.6 (3)	C10E—N1E—C19E—C20E	−51.5 (4)
C9D—C10D—N1D—C19D	−12.9 (4)	C13E—N1E—C19E—C20E	135.7 (3)
C11D—C10D—N1D—C13D	−18.1 (4)	C10E—N1E—C19E—C24E	131.1 (3)
C9D—C10D—N1D—C13D	162.5 (3)	C13E—N1E—C19E—C24E	−41.8 (4)
C10D—N1D—C19D—C20D	−56.9 (4)	C24E—C19E—C20E—C21E	−0.5 (5)
C13D—N1D—C19D—C20D	127.5 (3)	N1E—C19E—C20E—C21E	−178.0 (3)
C10D—N1D—C19D—C24D	126.0 (3)	C19E—C20E—C21E—C22E	0.8 (5)
C13D—N1D—C19D—C24D	−49.6 (4)	C20E—C21E—C22E—C23E	−0.8 (6)
C20D—C19D—C24D—C23D	0.1 (5)	C21E—C22E—C23E—C24E	0.6 (6)
N1D—C19D—C24D—C23D	177.3 (3)	C22E—C23E—C24E—C19E	−0.4 (6)
C19D—C24D—C23D—C22D	0.6 (5)	C20E—C19E—C24E—C23E	0.3 (5)
C24D—C23D—C22D—C21D	−1.2 (5)	N1E—C19E—C24E—C23E	177.8 (3)
C23D—C22D—C21D—C20D	1.1 (6)	C10E—N1E—C13E—C18E	−52.8 (4)
C24D—C19D—C20D—C21D	−0.2 (5)	C19E—N1E—C13E—C18E	120.3 (3)
N1D—C19D—C20D—C21D	−177.3 (3)	C10E—N1E—C13E—C14E	128.6 (3)
C22D—C21D—C20D—C19D	−0.3 (5)	C19E—N1E—C13E—C14E	−58.3 (4)
C10D—N1D—C13D—C14D	133.7 (3)	C14E—C13E—C18E—C17E	0.5 (5)
C19D—N1D—C13D—C14D	−50.6 (4)	N1E—C13E—C18E—C17E	−178.1 (3)
C10D—N1D—C13D—C18D	−49.1 (4)	C13E—C18E—C17E—C16E	0.0 (5)
C19D—N1D—C13D—C18D	126.5 (3)	C18E—C17E—C16E—C15E	−0.3 (5)
C14D—C13D—C18D—C17D	2.6 (4)	C17E—C16E—C15E—C14E	0.0 (5)
N1D—C13D—C18D—C17D	−174.5 (3)	C16E—C15E—C14E—C13E	0.5 (5)
C13D—C18D—C17D—C16D	0.6 (4)	C18E—C13E—C14E—C15E	−0.8 (5)
C18D—C17D—C16D—C15D	−1.9 (5)	N1E—C13E—C14E—C15E	177.9 (3)
C17D—C16D—C15D—C14D	0.1 (5)	N3D—C2D—S1D—C5D	0.8 (2)
C18D—C13D—C14D—C15D	−4.5 (4)	S2D—C2D—S1D—C5D	−179.0 (2)
N1D—C13D—C14D—C15D	172.7 (3)	C6D—C5D—S1D—C2D	177.7 (3)
C16D—C15D—C14D—C13D	3.1 (5)	C4D—C5D—S1D—C2D	−0.3 (2)
S2E—C2E—N3E—C4E	−176.9 (2)	C6E—C5E—S1E—C2E	−177.6 (3)
S1E—C2E—N3E—C4E	2.5 (4)	C4E—C5E—S1E—C2E	−0.8 (2)
C2E—N3E—C4E—O1E	175.9 (3)	N3E—C2E—S1E—C5E	−0.8 (2)
C2E—N3E—C4E—C5E	−3.1 (4)	S2E—C2E—S1E—C5E	178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3D—H3D···O1E	0.88	1.93	2.784 (3)	163
N3E—H3E···O1D	0.88	1.97	2.836 (3)	166

The interplanar angles (°) between the planes containing rings in investigated compounds 1–5 and other derivatives with crystal structures determined earlier, i.e. 6–9 Żesławska et al., 2022b; Smith et al., 2009). top

Compound	R/B	R/Ph1	R/Ph2	B/Ph1	B/Ph2	Ph1/Ph2
1	3.22 (2)	19.78 (2)	-	17.27 (2)	-	-
2	A:13.9 (2)	A:47.6 (1)	-	A:60.1 (2)	-	-
	B:44.2 (1)	B:44.2 (1)	-	B:60.9 (2)	-	-
3*	1.42 (6)	89.2 (1)	-	89.5 (1)	-	-
4	24.5 (1)	2.4 (1)	-	22.7 (1)	-	-
5*	D:7.3 (2)	D:64.9 (1)	D:55.2 (1)	D:61.1 (1)	D:61.9 (1)	D:77.0 (1)
	E:13.2 (1)	E:62.2 (1)	E:76.2 (1)	E:65.9 (1)	E:63.6 (1)	E:81.1 (1)
6	D:18.1 (1)	D:42.27 (7)	-	D:24.5 (1)	-	-
	E:15.7 (1)	E:36.12 (8)	-	E:20.6 (1)	-	-
7	D:6.0 (1)	D:23.5 (1)	-	D:19.4 (1)	-	-
	E:6.3 (1)	E:49.96 (9)	-	E:50 (1)	-	-
8*	7.3 (1)	64.91 (4)	52.23 (7)	70.24 (5)	56.06 (6)	85.18 (5)
9	6.80	1.63	-	8.11	-	-

Designation of rings: R is the rhodanine ring, B is the aromatic ring of the benzylidene moiety and Ph1/Ph2 are the other arene rings. Compounds showing an efflux modulating effect are depicted in an asterisk (*). Two molecules in the asymmetric unit are denoted `D' and `E'.

The interplanar angles (°) between the planes of the rings in the predicted best-scored docking poses top

Compound	R/B	R/Ph1	R/Ph2	B/Ph1	B/Ph2	Ph1/Ph2
3	19.7	42.8	-	41.1	-	-
5	18.8	45.2	44.2	56.4	57.4	71.2

Designation of rings: R is the rhodanine ring, B is the aromatic ring of the benzylidene moiety and Ph1/Ph2 are the other arene rings.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Architecture of the rings of 5-aryl­idenerhodanine derivatives versus P-gp inhibition

Supporting information

Architecture of the rings of 5-arylidenerhodanine derivatives versus P-gp inhibition