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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 35 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229623006502/yp3230sup1.cif
Contains datablocks global, 1, 2, 3, 4, 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32301sup2.hkl
Contains datablock 1

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32301sup7.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32302sup3.hkl
Contains datablock 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32302sup8.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32303sup4.hkl
Contains datablock 3

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32303sup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32304sup10.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623006502/yp32304sup5.hkl
Contains datablock 4

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623006502/yp32305sup11.cml
Supplementary material

hkl

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·C2H6OSZ = 2
Mr = 433.54F(000) = 452
Triclinic, P1Dx = 1.462 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3704 (1) ÅCell parameters from 78214 reflections
b = 8.7100 (1) Åθ = 2.4–51.7°
c = 16.4236 (1) ŵ = 0.40 mm1
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 Source17468 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.034
ω scansθmax = 51.9°, θmin = 2.5°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2018)
h = 1616
Tmin = 0.496, Tmax = 1k = 1919
156355 measured reflectionsl = 3636
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.0529P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
22177 reflectionsΔρmax = 0.62 e Å3
259 parametersΔρmin = 0.55 e Å3
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
xyzUiso*/Ueq
C181.13614 (6)0.91387 (5)0.34413 (2)0.01650 (6)
H181.1614670.9739750.3001120.02*
C171.22018 (7)0.98952 (5)0.42436 (3)0.01990 (7)
H171.3021861.100270.4345280.024*
C161.18472 (7)0.90374 (6)0.48981 (3)0.02020 (7)
H161.2425170.9552470.5445320.024*
C151.06376 (7)0.74183 (6)0.47422 (3)0.01881 (6)
H151.0385820.6826870.5186060.023*
C140.97924 (6)0.66574 (5)0.39395 (2)0.01619 (5)
H140.8966020.5552260.3842540.019*
C131.01464 (5)0.75036 (5)0.32713 (2)0.01310 (5)
C100.92967 (5)0.66943 (4)0.24103 (2)0.01260 (4)
C111.00447 (5)0.73464 (5)0.17238 (2)0.01433 (5)
H111.1102170.8333650.181070.017*
C120.92589 (5)0.65672 (5)0.09207 (2)0.01425 (5)
H120.9785510.7035210.0466990.017*
C70.77000 (5)0.50997 (5)0.07645 (2)0.01312 (5)
C80.69458 (6)0.44480 (5)0.14499 (2)0.01490 (5)
H80.5889760.345980.1363630.018*
C90.77305 (6)0.52358 (5)0.22512 (2)0.01454 (5)
H90.7193320.4775560.2705090.017*
C60.69889 (5)0.43480 (5)0.00947 (2)0.01400 (5)
H60.7666690.4909480.0492540.017*
C50.55140 (5)0.29748 (5)0.04161 (2)0.01363 (5)
C40.50873 (6)0.24339 (5)0.13265 (2)0.01416 (5)
N30.35370 (5)0.09788 (4)0.15123 (2)0.01454 (4)
C20.27093 (6)0.03606 (5)0.08568 (2)0.01483 (5)
O10.59204 (5)0.31031 (5)0.18570 (2)0.01887 (5)
C190.29317 (6)0.01487 (5)0.23614 (2)0.01622 (5)
H19A0.3126430.0971910.2730210.019*
H19B0.1544030.0479090.2424450.019*
C200.40484 (6)0.10124 (5)0.26202 (2)0.01392 (5)
O30.33248 (6)0.18963 (5)0.33648 (2)0.01985 (5)
O20.54190 (5)0.10860 (4)0.22010 (2)0.01785 (5)
C210.24174 (8)0.39188 (6)0.28782 (3)0.02420 (8)
H21A0.3446460.4132020.25190.036*
H21B0.152650.4504630.2746590.036*
H21C0.1724110.2738330.2787760.036*
C220.47559 (7)0.66789 (5)0.38776 (3)0.01811 (6)
H22A0.5511310.7234110.4412870.027*
H22B0.386370.7257250.3736430.027*
H22C0.5619650.6678990.3447750.027*
O40.49357 (6)0.37900 (4)0.40755 (2)0.02072 (6)
S10.38727 (2)0.16147 (2)0.00822 (2)0.01444 (2)
S20.08731 (2)0.13058 (2)0.09188 (2)0.02106 (2)
S30.34337 (2)0.46175 (2)0.39428 (2)0.01640 (2)
H30.4027 (14)0.2477 (13)0.3517 (6)0.030 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C180.02011 (14)0.01330 (12)0.01480 (12)0.00382 (11)0.00008 (10)0.00273 (9)
C170.02559 (18)0.01445 (13)0.01618 (13)0.00300 (12)0.00130 (12)0.00098 (10)
C160.02530 (18)0.01894 (15)0.01380 (12)0.00502 (13)0.00050 (12)0.00086 (11)
C150.02104 (16)0.02041 (16)0.01338 (12)0.00404 (13)0.00125 (11)0.00407 (11)
C140.01617 (13)0.01693 (13)0.01401 (11)0.00269 (11)0.00082 (10)0.00431 (10)
C130.01290 (11)0.01378 (11)0.01270 (10)0.00437 (9)0.00094 (8)0.00267 (8)
C100.01239 (11)0.01335 (11)0.01245 (10)0.00462 (9)0.00099 (8)0.00271 (8)
C110.01311 (11)0.01539 (12)0.01402 (11)0.00347 (10)0.00159 (9)0.00363 (9)
C120.01389 (11)0.01633 (12)0.01301 (11)0.00479 (10)0.00225 (9)0.00400 (9)
C70.01367 (11)0.01433 (11)0.01228 (10)0.00584 (9)0.00160 (8)0.00235 (8)
C80.01593 (12)0.01444 (12)0.01271 (11)0.00274 (10)0.00132 (9)0.00217 (9)
C90.01570 (12)0.01435 (12)0.01240 (11)0.00297 (10)0.00165 (9)0.00276 (9)
C60.01501 (12)0.01591 (12)0.01201 (10)0.00643 (10)0.00159 (9)0.00225 (9)
C50.01504 (12)0.01575 (12)0.01138 (10)0.00704 (10)0.00145 (8)0.00195 (9)
C40.01529 (12)0.01747 (13)0.01146 (10)0.00794 (10)0.00140 (9)0.00226 (9)
N30.01596 (11)0.01697 (11)0.01112 (9)0.00688 (9)0.00099 (8)0.00076 (8)
C20.01610 (12)0.01578 (12)0.01328 (11)0.00661 (10)0.00131 (9)0.00166 (9)
O10.02088 (12)0.02341 (14)0.01312 (10)0.00707 (11)0.00347 (9)0.00526 (9)
C190.01814 (13)0.01971 (14)0.01165 (11)0.00903 (12)0.00094 (9)0.00029 (10)
C200.01661 (12)0.01453 (12)0.01096 (10)0.00553 (10)0.00169 (9)0.00222 (8)
O30.02588 (14)0.02153 (13)0.01255 (9)0.01128 (11)0.00146 (9)0.00189 (9)
O20.01904 (12)0.02137 (13)0.01506 (10)0.01006 (10)0.00006 (8)0.00240 (9)
C210.02391 (19)0.01864 (16)0.02626 (19)0.00618 (14)0.00689 (15)0.00198 (14)
C220.02107 (15)0.01378 (13)0.01835 (14)0.00484 (11)0.00039 (11)0.00190 (10)
O40.03026 (16)0.01797 (12)0.01694 (11)0.01369 (12)0.00031 (10)0.00100 (9)
S10.01642 (4)0.01568 (4)0.01130 (3)0.00547 (3)0.00169 (2)0.00200 (2)
S20.02223 (5)0.01836 (4)0.01866 (4)0.00141 (4)0.00123 (3)0.00277 (3)
S30.01813 (4)0.01392 (4)0.01787 (4)0.00518 (3)0.00458 (3)0.00394 (3)
Geometric parameters (Å, º) top
C18—C171.3918 (6)C6—H60.95
C18—C131.4034 (5)C5—C41.4808 (5)
C18—H180.95C5—S11.7519 (4)
C17—C161.3926 (7)C4—O11.2149 (5)
C17—H170.95C4—N31.3965 (5)
C16—C151.3911 (7)N3—C21.3697 (5)
C16—H160.95N3—C191.4438 (5)
C15—C141.3941 (6)C2—S21.6352 (4)
C15—H150.95C2—S11.7474 (4)
C14—C131.4060 (5)C19—C201.5195 (5)
C14—H140.95C19—H19A0.99
C13—C101.4845 (5)C19—H19B0.99
C10—C91.4040 (5)C20—O21.2100 (5)
C10—C111.4057 (5)C20—O31.3239 (5)
C11—C121.3881 (5)O3—H30.852 (10)
C11—H110.95C21—S31.7946 (5)
C12—C71.4061 (5)C21—H21A0.98
C12—H120.95C21—H21B0.98
C7—C81.4055 (5)C21—H21C0.98
C7—C61.4527 (5)C22—S31.7822 (4)
C8—C91.3870 (5)C22—H22A0.98
C8—H80.95C22—H22B0.98
C9—H90.95C22—H22C0.98
C6—C51.3511 (5)O4—S31.5172 (4)
C17—C18—C13121.15 (4)C6—C5—C4119.99 (3)
C17—C18—H18119.4C6—C5—S1130.11 (3)
C13—C18—H18119.4C4—C5—S1109.89 (3)
C18—C17—C16120.36 (4)O1—C4—N3122.81 (3)
C18—C17—H17119.8O1—C4—C5127.34 (4)
C16—C17—H17119.8N3—C4—C5109.85 (3)
C15—C16—C17119.31 (4)C2—N3—C4117.03 (3)
C15—C16—H16120.3C2—N3—C19122.73 (4)
C17—C16—H16120.3C4—N3—C19120.17 (3)
C16—C15—C14120.48 (4)N3—C2—S2125.95 (3)
C16—C15—H15119.8N3—C2—S1110.70 (3)
C14—C15—H15119.8S2—C2—S1123.35 (2)
C15—C14—C13120.89 (4)N3—C19—C20111.45 (3)
C15—C14—H14119.6N3—C19—H19A109.3
C13—C14—H14119.6C20—C19—H19A109.3
C18—C13—C14117.81 (3)N3—C19—H19B109.3
C18—C13—C10120.74 (3)C20—C19—H19B109.3
C14—C13—C10121.43 (3)H19A—C19—H19B108
C9—C10—C11117.51 (3)O2—C20—O3125.60 (4)
C9—C10—C13121.18 (3)O2—C20—C19123.98 (3)
C11—C10—C13121.31 (3)O3—C20—C19110.41 (3)
C12—C11—C10120.89 (3)C20—O3—H3109.0 (7)
C12—C11—H11119.6S3—C21—H21A109.5
C10—C11—H11119.6S3—C21—H21B109.5
C11—C12—C7121.39 (3)H21A—C21—H21B109.5
C11—C12—H12119.3S3—C21—H21C109.5
C7—C12—H12119.3H21A—C21—H21C109.5
C8—C7—C12117.83 (3)H21B—C21—H21C109.5
C8—C7—C6124.33 (3)S3—C22—H22A109.5
C12—C7—C6117.84 (3)S3—C22—H22B109.5
C9—C8—C7120.55 (3)H22A—C22—H22B109.5
C9—C8—H8119.7S3—C22—H22C109.5
C7—C8—H8119.7H22A—C22—H22C109.5
C8—C9—C10121.84 (3)H22B—C22—H22C109.5
C8—C9—H9119.1C2—S1—C592.503 (18)
C10—C9—H9119.1O4—S3—C22105.27 (2)
C5—C6—C7130.07 (4)O4—S3—C21106.39 (2)
C5—C6—H6115C22—S3—C2198.47 (2)
C7—C6—H6115
C13—C18—C17—C160.11 (7)C12—C7—C6—C5178.76 (4)
C18—C17—C16—C150.26 (8)C7—C6—C5—C4178.80 (4)
C17—C16—C15—C140.21 (8)C7—C6—C5—S11.72 (7)
C16—C15—C14—C130.21 (7)C6—C5—C4—O10.76 (6)
C17—C18—C13—C140.51 (6)S1—C5—C4—O1178.82 (4)
C17—C18—C13—C10178.42 (4)C6—C5—C4—N3178.85 (3)
C15—C14—C13—C180.56 (6)S1—C5—C4—N31.57 (4)
C15—C14—C13—C10178.36 (4)O1—C4—N3—C2179.25 (4)
C18—C13—C10—C9163.79 (4)C5—C4—N3—C21.12 (5)
C14—C13—C10—C917.31 (6)O1—C4—N3—C193.82 (6)
C18—C13—C10—C1117.06 (6)C5—C4—N3—C19175.81 (3)
C14—C13—C10—C11161.83 (4)C4—N3—C2—S2179.30 (3)
C9—C10—C11—C120.17 (6)C19—N3—C2—S23.85 (6)
C13—C10—C11—C12179.01 (3)C4—N3—C2—S10.14 (4)
C10—C11—C12—C70.33 (6)C19—N3—C2—S1176.71 (3)
C11—C12—C7—C80.52 (6)C2—N3—C19—C2089.99 (5)
C11—C12—C7—C6178.83 (3)C4—N3—C19—C2086.77 (4)
C12—C7—C8—C90.20 (6)N3—C19—C20—O28.07 (6)
C6—C7—C8—C9179.09 (4)N3—C19—C20—O3172.83 (4)
C7—C8—C9—C100.30 (6)N3—C2—S1—C50.71 (3)
C11—C10—C9—C80.48 (6)S2—C2—S1—C5179.84 (3)
C13—C10—C9—C8178.69 (4)C6—C5—S1—C2179.18 (4)
C8—C7—C6—C51.94 (7)C4—C5—S1—C21.30 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O4i0.85 (1)1.75 (1)2.5768 (5)165 (1)
C12—H12···S2ii0.952.93.8415 (4)170
C17—H17···O4ii0.952.523.4320 (6)160
C16—H16···O3iii0.952.643.2927 (6)127
C8—H8···O2i0.952.633.3683 (5)135
C21—H21A···O1iv0.982.713.2638 (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
C20H17NO3S2F(000) = 800
Mr = 383.46Dx = 1.42 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 37361 reflections
a = 5.14350 (4) Åθ = 4.0–76.4°
b = 66.3783 (5) ŵ = 2.86 mm1
c = 5.34343 (5) ÅT = 100 K
β = 100.4548 (8)°Plate, colourless
V = 1794.05 (3) Å30.16 × 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 Source3694 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.035
ω scansθmax = 76.6°, θmin = 4.0°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2018)
h = 65
Tmin = 0.637, Tmax = 1k = 8382
55674 measured reflectionsl = 66
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0097P)2 + 2.0556P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max = 0.001
S = 1.15Δρmax = 0.31 e Å3
3746 reflectionsΔρmin = 0.23 e Å3
310 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00037 (8)
Primary atom site location: structure-invariant direct methods
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
xyzUiso*/UeqOcc. (<1)
S10.83155 (9)0.10860 (2)0.05764 (9)0.02083 (11)
S21.06564 (8)0.08008 (2)0.26499 (8)0.01863 (11)
O21.3471 (2)0.01197 (2)0.2478 (2)0.0196 (3)
O31.2570 (2)0.01440 (2)0.6408 (2)0.0210 (3)
H31.3860540.0064810.6744490.031*
C231.2143 (3)0.01878 (2)0.3962 (3)0.0151 (3)
C220.9883 (3)0.03311 (2)0.3196 (3)0.0159 (3)
H22A1.0358610.0463870.3993690.019*
H22B0.8317630.0280340.3839060.019*
C210.9175 (3)0.03573 (2)0.0331 (3)0.0164 (3)
H21A0.8760220.0223480.0459740.02*
H21B1.0735190.0410870.0295690.02*
C200.6841 (3)0.04972 (2)0.0531 (3)0.0158 (3)
H20A0.646830.0500530.2414140.019*
H20B0.5267220.0440170.0036510.019*
N30.7219 (3)0.07062 (2)0.0419 (3)0.0141 (3)
C20.8719 (3)0.08435 (2)0.0589 (3)0.0164 (3)
C40.5761 (3)0.07809 (2)0.2198 (3)0.0152 (3)
C50.6089 (3)0.10026 (2)0.2457 (3)0.0165 (3)
O10.4417 (2)0.06758 (2)0.3308 (2)0.0188 (3)
C60.4731 (3)0.11055 (3)0.3959 (3)0.0185 (3)
H60.368950.1023490.4850210.022*
C70.4566 (3)0.13198 (3)0.4469 (3)0.0184 (3)
C100.3875 (4)0.17305 (3)0.5628 (4)0.0229 (4)
C130.3470 (4)0.19458 (3)0.6220 (4)0.0267 (4)
C160.2597 (5)0.23498 (3)0.7358 (5)0.0380 (5)
H160.2395540.2487310.7778820.046*0.508 (3)
H16A0.2274230.2488920.7588430.046*0.492 (3)
C18A0.2906 (8)0.20890 (6)0.4176 (9)0.0314 (9)0.508 (3)
H18A0.2838280.2047140.2465240.038*0.508 (3)
C17A0.2461 (8)0.22897 (6)0.4726 (9)0.0360 (10)0.508 (3)
H17A0.2072720.2386020.3396040.043*0.508 (3)
C14A0.3474 (8)0.20106 (6)0.8619 (8)0.0322 (9)0.508 (3)
H14A0.3806950.1916430.9977670.039*0.508 (3)
C15A0.3004 (9)0.22114 (6)0.9162 (9)0.0374 (11)0.508 (3)
H15A0.2976490.2249571.0870420.045*0.508 (3)
C12A0.6268 (10)0.14680 (7)0.3876 (10)0.0226 (10)0.508 (3)
H12A0.7667310.1430840.3027220.027*0.508 (3)
C11A0.5974 (10)0.16678 (6)0.4492 (10)0.0244 (9)0.508 (3)
H11A0.7222880.1764130.4135330.029*0.508 (3)
C9A0.2211 (11)0.15826 (9)0.6317 (11)0.0228 (11)0.508 (3)
H9A0.0842780.1620020.7203840.027*0.508 (3)
C8A0.2525 (11)0.13822 (9)0.5729 (11)0.0229 (11)0.508 (3)
H8A0.1340270.1284660.6182770.027*0.508 (3)
C18B0.5650 (8)0.20787 (6)0.6876 (8)0.0288 (9)0.492 (3)
H18B0.7396690.2030790.6913810.035*0.492 (3)
C17B0.5234 (9)0.22789 (6)0.7463 (9)0.0330 (10)0.492 (3)
H17B0.6691540.2367630.7928730.04*0.492 (3)
C14B0.0991 (8)0.20192 (6)0.6353 (8)0.0297 (9)0.492 (3)
H14B0.0480720.1930390.6037390.036*0.492 (3)
C15B0.0584 (9)0.22196 (6)0.6935 (9)0.0339 (10)0.492 (3)
H15B0.1147840.2264490.7033020.041*0.492 (3)
C12B0.5327 (11)0.14716 (7)0.2922 (10)0.0232 (10)0.492 (3)
H12B0.6101350.1436280.1498450.028*0.492 (3)
C11B0.4954 (10)0.16736 (7)0.3461 (10)0.0250 (10)0.492 (3)
H11B0.5426550.1774710.2367450.03*0.492 (3)
C9B0.3101 (11)0.15784 (10)0.7101 (12)0.0227 (12)0.492 (3)
H9B0.2321770.161270.8526040.027*0.492 (3)
C8B0.3432 (11)0.13778 (9)0.6552 (11)0.0217 (11)0.492 (3)
H8B0.2880870.1277150.760710.026*0.492 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0223 (2)0.01499 (19)0.0284 (2)0.00131 (16)0.01314 (17)0.00002 (16)
S20.0173 (2)0.0205 (2)0.0197 (2)0.00009 (15)0.00783 (15)0.00062 (15)
O20.0179 (6)0.0229 (6)0.0190 (6)0.0060 (5)0.0063 (5)0.0018 (5)
O30.0220 (6)0.0245 (6)0.0168 (6)0.0098 (5)0.0046 (5)0.0021 (5)
C230.0141 (8)0.0140 (7)0.0174 (8)0.0026 (6)0.0033 (6)0.0001 (6)
C220.0146 (8)0.0155 (7)0.0182 (8)0.0013 (6)0.0046 (6)0.0001 (6)
C210.0145 (8)0.0171 (8)0.0177 (8)0.0026 (6)0.0036 (6)0.0003 (6)
C200.0139 (7)0.0151 (7)0.0184 (8)0.0006 (6)0.0027 (6)0.0013 (6)
N30.0108 (6)0.0155 (6)0.0165 (7)0.0010 (5)0.0033 (5)0.0013 (5)
C20.0139 (8)0.0171 (8)0.0175 (8)0.0006 (6)0.0008 (6)0.0021 (6)
C40.0122 (7)0.0178 (8)0.0153 (8)0.0023 (6)0.0016 (6)0.0016 (6)
C50.0144 (8)0.0170 (8)0.0178 (8)0.0002 (6)0.0022 (6)0.0021 (6)
O10.0176 (6)0.0196 (6)0.0207 (6)0.0013 (5)0.0077 (5)0.0014 (5)
C60.0175 (8)0.0186 (8)0.0200 (8)0.0000 (6)0.0046 (6)0.0026 (6)
C70.0154 (8)0.0188 (8)0.0204 (8)0.0021 (6)0.0019 (6)0.0003 (6)
C100.0194 (9)0.0194 (8)0.0289 (10)0.0019 (7)0.0021 (7)0.0023 (7)
C130.0245 (9)0.0193 (9)0.0365 (11)0.0014 (7)0.0062 (8)0.0030 (8)
C160.0383 (12)0.0180 (9)0.0592 (15)0.0017 (8)0.0124 (11)0.0063 (9)
C18A0.029 (2)0.0219 (18)0.043 (2)0.0031 (15)0.0064 (17)0.0014 (16)
C17A0.027 (2)0.0208 (19)0.060 (3)0.0020 (15)0.0083 (19)0.0041 (18)
C14A0.033 (2)0.0238 (19)0.038 (2)0.0029 (16)0.0015 (17)0.0048 (16)
C15A0.034 (2)0.028 (2)0.049 (3)0.0033 (17)0.0048 (19)0.0141 (19)
C12A0.018 (2)0.023 (2)0.028 (3)0.0001 (19)0.0088 (18)0.001 (2)
C11A0.022 (2)0.0196 (19)0.034 (3)0.0010 (18)0.0092 (19)0.0005 (19)
C9A0.022 (3)0.020 (2)0.027 (3)0.004 (2)0.006 (2)0.003 (2)
C8A0.021 (3)0.020 (2)0.029 (3)0.002 (2)0.008 (2)0.000 (2)
C18B0.026 (2)0.0219 (19)0.040 (2)0.0005 (15)0.0084 (17)0.0053 (16)
C17B0.037 (2)0.0204 (19)0.043 (2)0.0047 (17)0.0088 (19)0.0063 (17)
C14B0.027 (2)0.0206 (19)0.041 (2)0.0023 (15)0.0050 (17)0.0053 (16)
C15B0.031 (2)0.024 (2)0.046 (3)0.0080 (17)0.0060 (19)0.0041 (18)
C12B0.026 (3)0.020 (2)0.025 (3)0.003 (2)0.0066 (19)0.001 (2)
C11B0.022 (2)0.020 (2)0.032 (3)0.0021 (18)0.0043 (19)0.0041 (19)
C9B0.022 (3)0.024 (2)0.021 (3)0.004 (2)0.003 (2)0.002 (2)
C8B0.021 (3)0.021 (2)0.023 (3)0.003 (2)0.0046 (19)0.002 (2)
Geometric parameters (Å, º) top
S1—C21.7522 (17)C13—C14A1.352 (5)
S1—C51.7449 (17)C13—C18B1.420 (4)
S2—C21.6384 (17)C13—C14B1.379 (4)
O2—C231.223 (2)C16—H160.95
O3—H30.84C16—H16A0.95
O3—C231.318 (2)C16—C17A1.451 (5)
C23—C221.501 (2)C16—C15A1.320 (5)
C22—H22A0.99C16—C17B1.427 (5)
C22—H22B0.99C16—C15B1.336 (5)
C22—C211.518 (2)C18A—H18A0.95
C21—H21A0.99C18A—C17A1.392 (5)
C21—H21B0.99C17A—H17A0.95
C21—C201.522 (2)C14A—H14A0.95
C20—H20A0.99C14A—C15A1.394 (5)
C20—H20B0.99C15A—H15A0.95
C20—N31.477 (2)C12A—H12A0.95
N3—C21.366 (2)C12A—C11A1.382 (7)
N3—C41.404 (2)C11A—H11A0.95
C4—C51.485 (2)C9A—H9A0.95
C4—O11.210 (2)C9A—C8A1.383 (8)
C5—C61.343 (2)C8A—H8A0.95
C6—H60.95C18B—H18B0.95
C6—C71.454 (2)C18B—C17B1.391 (5)
C7—C12A1.391 (5)C17B—H17B0.95
C7—C8A1.408 (6)C14B—H14B0.95
C7—C12B1.403 (5)C14B—C15B1.390 (5)
C7—C8B1.401 (6)C15B—H15B0.95
C10—C131.487 (2)C12B—H12B0.95
C10—C11A1.395 (5)C12B—C11B1.392 (7)
C10—C9A1.395 (7)C11B—H11B0.95
C10—C11B1.423 (5)C9B—H9B0.95
C10—C9B1.383 (7)C9B—C8B1.381 (9)
C13—C18A1.437 (4)C8B—H8B0.95
C5—S1—C292.62 (8)C14B—C13—C18B117.7 (3)
C23—O3—H3109.5C17A—C16—H16120.4
O2—C23—O3123.32 (15)C15A—C16—H16120.4
O2—C23—C22123.60 (15)C15A—C16—C17A119.3 (3)
O3—C23—C22113.07 (14)C17B—C16—H16A120.2
C23—C22—H22A109.1C15B—C16—H16A120.2
C23—C22—H22B109.1C15B—C16—C17B119.7 (3)
C23—C22—C21112.32 (13)C13—C18A—H18A120.3
H22A—C22—H22B107.9C17A—C18A—C13119.4 (4)
C21—C22—H22A109.1C17A—C18A—H18A120.3
C21—C22—H22B109.1C16—C17A—H17A120.4
C22—C21—H21A108.8C18A—C17A—C16119.2 (4)
C22—C21—H21B108.8C18A—C17A—H17A120.4
C22—C21—C20113.99 (13)C13—C14A—H14A119
H21A—C21—H21B107.7C13—C14A—C15A122.1 (4)
C20—C21—H21A108.8C15A—C14A—H14A119
C20—C21—H21B108.8C16—C15A—C14A121.6 (4)
C21—C20—H20A108.5C16—C15A—H15A119.2
C21—C20—H20B108.5C14A—C15A—H15A119.2
H20A—C20—H20B107.5C7—C12A—H12A119.2
N3—C20—C21114.96 (13)C11A—C12A—C7121.6 (4)
N3—C20—H20A108.5C11A—C12A—H12A119.2
N3—C20—H20B108.5C10—C11A—H11A119.4
C2—N3—C20122.61 (14)C12A—C11A—C10121.2 (4)
C2—N3—C4116.15 (13)C12A—C11A—H11A119.4
C4—N3—C20120.75 (13)C10—C9A—H9A119.5
S2—C2—S1121.56 (10)C8A—C9A—C10121.0 (5)
N3—C2—S1111.16 (12)C8A—C9A—H9A119.5
N3—C2—S2127.28 (13)C7—C8A—H8A119.4
N3—C4—C5110.33 (13)C9A—C8A—C7121.3 (5)
O1—C4—N3123.43 (15)C9A—C8A—H8A119.4
O1—C4—C5126.23 (15)C13—C18B—H18B119.9
C4—C5—S1109.65 (12)C17B—C18B—C13120.2 (4)
C6—C5—S1130.55 (13)C17B—C18B—H18B119.9
C6—C5—C4119.80 (15)C16—C17B—H17B120.3
C5—C6—H6114.2C18B—C17B—C16119.3 (4)
C5—C6—C7131.60 (16)C18B—C17B—H17B120.3
C7—C6—H6114.2C13—C14B—H14B119.1
C12A—C7—C6126.1 (2)C13—C14B—C15B121.8 (4)
C12A—C7—C8A117.1 (3)C15B—C14B—H14B119.1
C8A—C7—C6116.8 (3)C16—C15B—C14B120.9 (4)
C12B—C7—C6124.1 (3)C16—C15B—H15B119.5
C8B—C7—C6117.7 (3)C14B—C15B—H15B119.5
C8B—C7—C12B118.1 (3)C7—C12B—H12B119.8
C11A—C10—C13122.0 (2)C11B—C12B—C7120.4 (4)
C11A—C10—C9A117.7 (3)C11B—C12B—H12B119.8
C9A—C10—C13120.3 (3)C10—C11B—H11B119.6
C11B—C10—C13121.3 (2)C12B—C11B—C10120.8 (4)
C9B—C10—C13121.0 (3)C12B—C11B—H11B119.6
C9B—C10—C11B117.7 (3)C10—C9B—H9B119.2
C18A—C13—C10119.4 (2)C8B—C9B—C10121.6 (5)
C14A—C13—C10122.1 (2)C8B—C9B—H9B119.2
C14A—C13—C18A118.4 (3)C7—C8B—H8B119.4
C18B—C13—C10121.0 (2)C9B—C8B—C7121.3 (5)
C14B—C13—C10121.1 (2)C9B—C8B—H8B119.4
S1—C5—C6—C72.5 (3)C10—C13—C18B—C17B179.0 (3)
O2—C23—C22—C218.5 (2)C10—C13—C14B—C15B179.2 (3)
O3—C23—C22—C21172.05 (14)C10—C9A—C8A—C71.5 (7)
C23—C22—C21—C20178.44 (13)C10—C9B—C8B—C70.1 (7)
C22—C21—C20—N360.87 (19)C13—C10—C11A—C12A177.8 (4)
C21—C20—N3—C277.00 (19)C13—C10—C9A—C8A178.5 (4)
C21—C20—N3—C4111.39 (16)C13—C10—C11B—C12B180.0 (4)
C20—N3—C2—S1169.93 (11)C13—C10—C9B—C8B179.1 (4)
C20—N3—C2—S29.2 (2)C13—C18A—C17A—C160.5 (5)
C20—N3—C4—C5168.71 (13)C13—C14A—C15A—C161.8 (6)
C20—N3—C4—O110.4 (2)C13—C18B—C17B—C161.0 (6)
N3—C4—C5—S13.22 (16)C13—C14B—C15B—C160.9 (7)
N3—C4—C5—C6176.12 (15)C18A—C13—C14A—C15A1.3 (5)
C2—S1—C5—C41.84 (12)C17A—C16—C15A—C14A4.1 (6)
C2—S1—C5—C6177.40 (17)C14A—C13—C18A—C17A1.8 (5)
C2—N3—C4—C53.43 (19)C15A—C16—C17A—C18A3.5 (5)
C2—N3—C4—O1177.47 (15)C12A—C7—C8A—C9A0.8 (6)
C4—N3—C2—S12.04 (18)C11A—C10—C13—C18A63.7 (4)
C4—N3—C2—S2178.78 (12)C11A—C10—C13—C14A119.9 (4)
C4—C5—C6—C7176.66 (17)C11A—C10—C9A—C8A4.5 (6)
C5—S1—C2—S2179.23 (11)C9A—C10—C13—C18A119.5 (4)
C5—S1—C2—N30.00 (13)C9A—C10—C13—C14A56.9 (4)
C5—C6—C7—C12A14.6 (4)C9A—C10—C11A—C12A5.3 (6)
C5—C6—C7—C8A166.9 (3)C8A—C7—C12A—C11A0.1 (6)
C5—C6—C7—C12B17.6 (4)C18B—C13—C14B—C15B4.3 (6)
C5—C6—C7—C8B166.3 (3)C17B—C16—C15B—C14B6.2 (6)
O1—C4—C5—S1177.70 (14)C14B—C13—C18B—C17B4.1 (5)
O1—C4—C5—C63.0 (3)C15B—C16—C17B—C18B6.3 (6)
C6—C7—C12A—C11A178.6 (4)C12B—C7—C8B—C9B0.9 (6)
C6—C7—C8A—C9A179.5 (4)C11B—C10—C13—C18B65.1 (4)
C6—C7—C12B—C11B176.0 (4)C11B—C10—C13—C14B120.2 (4)
C6—C7—C8B—C9B177.2 (4)C11B—C10—C9B—C8B2.0 (6)
C7—C12A—C11A—C103.1 (7)C9B—C10—C13—C18B117.9 (4)
C7—C12B—C11B—C102.0 (7)C9B—C10—C13—C14B56.8 (4)
C10—C13—C18A—C17A178.4 (3)C9B—C10—C11B—C12B2.9 (6)
C10—C13—C14A—C15A177.8 (3)C8B—C7—C12B—C11B0.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.841.832.669 (2)176
C22—H22A···S2ii0.992.853.806 (2)162
C22—H22A···O1iii0.992.603.260 (2)124
C21—H21B···S20.992.873.497 (2)122
C20—H20A···O1iv0.992.613.509 (2)151
C6—H6···S2v0.952.683.625 (2)178
Symmetry codes: (i) x+3, y, z+1; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x, y, z1; (v) x1, y, z+1.
5-(4-(Benzyloxy)benzylidene)-2-thioxothiazolidin-4-one (3) top
Crystal data top
C17H13NO2S2Z = 2
Mr = 327.4F(000) = 340
Triclinic, P1Dx = 1.471 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0091 (10) ÅCell parameters from 2831 reflections
b = 10.1386 (9) Åθ = 3.7–27.9°
c = 10.8157 (12) ŵ = 0.37 mm1
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 Source2390 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.061
Detector resolution: 10.3756 pixels mm-1θmax = 28.4°, θmin = 2.7°
ω scansh = 89
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2022)
k = 1312
Tmin = 0.624, Tmax = 1l = 1413
8387 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.076H-atom parameters constrained
wR(F2) = 0.224 w = 1/[σ2(Fo2) + (0.1204P)2 + 0.7354P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3370 reflectionsΔρmax = 0.85 e Å3
199 parametersΔρmin = 0.86 e Å3
0 restraints
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
xyzUiso*/Ueq
S10.78314 (14)0.67205 (9)1.13843 (8)0.0244 (3)
S20.88064 (16)0.87817 (9)1.35525 (9)0.0300 (3)
O10.9381 (4)0.3904 (3)1.3601 (3)0.0297 (6)
C20.8654 (5)0.7228 (4)1.3011 (3)0.0223 (8)
N30.9150 (5)0.6158 (3)1.3721 (3)0.0246 (7)
H30.9564110.624621.4565120.03*
C40.8977 (6)0.4937 (4)1.3068 (3)0.0229 (8)
O40.5459 (4)0.3078 (2)0.5468 (2)0.0268 (6)
C50.8254 (5)0.5053 (3)1.1667 (3)0.0219 (8)
C60.8057 (5)0.3996 (4)1.0852 (4)0.0239 (8)
H60.8412630.3196491.1257240.029*
C70.7402 (6)0.3827 (4)0.9458 (3)0.0227 (8)
C80.6813 (5)0.4844 (4)0.8617 (4)0.0225 (8)
H80.6835580.57310.8960170.027*
C90.6205 (6)0.4570 (4)0.7301 (3)0.0235 (8)
H90.5840270.5270750.6749370.028*
C100.6122 (5)0.3264 (4)0.6774 (3)0.0222 (8)
C110.6740 (6)0.2243 (3)0.7582 (3)0.0239 (8)
H110.6728860.1358390.7236390.029*
C120.7371 (6)0.2541 (4)0.8900 (4)0.0248 (8)
H120.7800310.1843570.9445720.03*
C130.5448 (6)0.1725 (4)0.4953 (3)0.0271 (8)
H13A0.4781720.1139720.5420810.033*
H13B0.6826860.1440610.5077240.033*
C140.4383 (6)0.1602 (3)0.3540 (4)0.0257 (8)
C150.2362 (6)0.1391 (4)0.3169 (4)0.0289 (9)
H150.1636250.1418140.3796260.035*
C160.1380 (6)0.1138 (4)0.1878 (4)0.0317 (9)
H160.0012940.0977220.1628860.038*
C170.2409 (7)0.1119 (4)0.0959 (4)0.0342 (10)
H170.1731660.094570.0077280.041*
C180.4424 (7)0.1353 (4)0.1323 (4)0.0361 (10)
H180.5138310.1345150.0689350.043*
C190.5428 (7)0.1602 (4)0.2619 (4)0.0333 (9)
H190.6819330.1771190.286720.04*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0348 (6)0.0152 (5)0.0244 (5)0.0036 (4)0.0092 (4)0.0061 (3)
S20.0427 (6)0.0161 (5)0.0327 (6)0.0047 (4)0.0130 (4)0.0029 (4)
O10.0447 (17)0.0165 (13)0.0277 (14)0.0001 (12)0.0086 (12)0.0057 (11)
C20.0270 (19)0.0169 (17)0.0257 (18)0.0019 (14)0.0104 (15)0.0078 (14)
N30.0353 (19)0.0159 (15)0.0228 (15)0.0019 (13)0.0077 (13)0.0037 (12)
C40.028 (2)0.0178 (17)0.0249 (18)0.0003 (15)0.0113 (15)0.0032 (14)
O40.0428 (16)0.0139 (12)0.0228 (13)0.0028 (11)0.0072 (11)0.0036 (10)
C50.0239 (18)0.0173 (17)0.0268 (18)0.0029 (14)0.0099 (14)0.0056 (14)
C60.029 (2)0.0167 (17)0.0282 (19)0.0018 (15)0.0102 (15)0.0080 (14)
C70.027 (2)0.0202 (18)0.0226 (17)0.0011 (15)0.0097 (14)0.0055 (14)
C80.0269 (19)0.0126 (16)0.0301 (19)0.0019 (14)0.0114 (15)0.0009 (14)
C90.029 (2)0.0172 (17)0.0266 (19)0.0019 (15)0.0109 (15)0.0076 (14)
C100.0267 (19)0.0192 (18)0.0224 (18)0.0045 (14)0.0096 (15)0.0027 (14)
C110.031 (2)0.0150 (17)0.0262 (19)0.0022 (15)0.0085 (15)0.0028 (14)
C120.028 (2)0.0197 (18)0.0272 (19)0.0001 (15)0.0068 (15)0.0058 (15)
C130.039 (2)0.0150 (17)0.0257 (19)0.0001 (15)0.0057 (16)0.0006 (14)
C140.039 (2)0.0111 (16)0.0282 (19)0.0012 (15)0.0097 (16)0.0053 (14)
C150.037 (2)0.0191 (18)0.031 (2)0.0013 (16)0.0110 (17)0.0046 (15)
C160.038 (2)0.0210 (19)0.032 (2)0.0036 (17)0.0012 (17)0.0068 (16)
C170.057 (3)0.0188 (19)0.0227 (19)0.0092 (18)0.0027 (18)0.0070 (15)
C180.055 (3)0.026 (2)0.033 (2)0.0052 (19)0.021 (2)0.0074 (17)
C190.044 (3)0.023 (2)0.034 (2)0.0082 (18)0.0131 (18)0.0025 (16)
Geometric parameters (Å, º) top
S1—C21.741 (4)C10—C111.395 (5)
S1—C51.752 (4)C11—H110.95
S2—C21.639 (4)C11—C121.388 (5)
O1—C41.227 (4)C12—H120.95
C2—N31.363 (4)C13—H13A0.99
N3—H30.88C13—H13B0.99
N3—C41.375 (5)C13—C141.508 (5)
C4—C51.478 (5)C14—C151.375 (6)
O4—C101.365 (4)C14—C191.384 (6)
O4—C131.448 (4)C15—H150.95
C5—C61.327 (5)C15—C161.388 (5)
C6—H60.95C16—H160.95
C6—C71.452 (5)C16—C171.374 (6)
C7—C81.411 (5)C17—H170.95
C7—C121.400 (5)C17—C181.374 (6)
C8—H80.95C18—H180.95
C8—C91.382 (5)C18—C191.397 (6)
C9—H90.95C19—H190.95
C9—C101.403 (5)
C2—S1—C593.04 (17)C12—C11—C10118.9 (3)
S2—C2—S1123.1 (2)C12—C11—H11120.5
N3—C2—S1110.0 (3)C7—C12—H12118.6
N3—C2—S2126.8 (3)C11—C12—C7122.8 (3)
C2—N3—H3121.3C11—C12—H12118.6
C2—N3—C4117.5 (3)O4—C13—H13A109.5
C4—N3—H3121.3O4—C13—H13B109.5
O1—C4—N3123.5 (3)O4—C13—C14110.6 (3)
O1—C4—C5125.7 (3)H13A—C13—H13B108.1
N3—C4—C5110.9 (3)C14—C13—H13A109.5
C10—O4—C13115.3 (3)C14—C13—H13B109.5
C4—C5—S1108.5 (3)C15—C14—C13119.3 (3)
C6—C5—S1130.6 (3)C15—C14—C19119.7 (4)
C6—C5—C4120.8 (3)C19—C14—C13120.8 (4)
C5—C6—H6113.9C14—C15—H15119.9
C5—C6—C7132.3 (3)C14—C15—C16120.2 (4)
C7—C6—H6113.9C16—C15—H15119.9
C8—C7—C6125.8 (3)C15—C16—H16119.8
C12—C7—C6117.1 (3)C17—C16—C15120.5 (4)
C12—C7—C8117.1 (3)C17—C16—H16119.8
C7—C8—H8119.5C16—C17—H17120.2
C9—C8—C7121.0 (3)C18—C17—C16119.6 (4)
C9—C8—H8119.5C18—C17—H17120.2
C8—C9—H9119.8C17—C18—H18119.8
C8—C9—C10120.5 (3)C17—C18—C19120.4 (4)
C10—C9—H9119.8C19—C18—H18119.8
O4—C10—C9116.7 (3)C14—C19—C18119.6 (4)
O4—C10—C11123.7 (3)C14—C19—H19120.2
C11—C10—C9119.7 (3)C18—C19—H19120.2
C10—C11—H11120.5
S1—C2—N3—C41.6 (4)C6—C7—C12—C11178.7 (3)
S1—C5—C6—C71.2 (7)C7—C8—C9—C101.3 (5)
S2—C2—N3—C4177.6 (3)C8—C7—C12—C111.9 (5)
O1—C4—C5—S1178.5 (3)C8—C9—C10—O4178.4 (3)
O1—C4—C5—C62.7 (6)C8—C9—C10—C112.8 (5)
C2—S1—C5—C42.1 (3)C9—C10—C11—C121.9 (5)
C2—S1—C5—C6176.6 (4)C10—O4—C13—C14170.6 (3)
C2—N3—C4—O1179.9 (4)C10—C11—C12—C70.5 (6)
C2—N3—C4—C50.0 (5)C12—C7—C8—C91.0 (5)
N3—C4—C5—S11.6 (4)C13—O4—C10—C9178.2 (3)
N3—C4—C5—C6177.2 (3)C13—O4—C10—C110.5 (5)
C4—C5—C6—C7179.7 (4)C13—C14—C15—C16173.3 (3)
O4—C10—C11—C12179.4 (3)C13—C14—C19—C18173.6 (4)
O4—C13—C14—C1586.6 (4)C14—C15—C16—C171.2 (6)
O4—C13—C14—C1998.1 (4)C15—C14—C19—C181.7 (6)
C5—S1—C2—S2177.1 (3)C15—C16—C17—C180.0 (6)
C5—S1—C2—N32.2 (3)C16—C17—C18—C190.3 (6)
C5—C6—C7—C80.8 (7)C17—C18—C19—C140.5 (6)
C5—C6—C7—C12179.8 (4)C19—C14—C15—C162.0 (5)
C6—C7—C8—C9179.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.881.942.810 (4)169
C17—H17···S1ii0.952.983.422 (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
C21H19NO4S2Z = 2
Mr = 413.49F(000) = 432
Triclinic, P1Dx = 1.425 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0919 (4) ÅCell parameters from 4931 reflections
b = 7.3014 (4) Åθ = 3.0–28.7°
c = 20.1260 (12) ŵ = 0.31 mm1
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 Source3575 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.036
Detector resolution: 10.3756 pixels mm-1θmax = 28.7°, θmin = 3.0°
ω scansh = 99
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
k = 99
Tmin = 0.897, Tmax = 0.981l = 2626
12987 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0271P)2 + 1.7628P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
4501 reflectionsΔρmax = 0.38 e Å3
254 parametersΔρmin = 0.39 e Å3
0 restraints
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
xyzUiso*/Ueq
C150.5416 (4)0.1330 (4)0.34652 (14)0.0237 (6)
H150.5634710.0938160.3912790.028*
C160.7067 (4)0.1142 (4)0.30211 (15)0.0279 (6)
H160.8407010.0635620.3169660.033*
C170.6785 (4)0.1684 (4)0.23651 (15)0.0279 (6)
H170.7922480.1530780.2062290.034*
C180.4821 (5)0.2455 (4)0.21552 (15)0.0284 (6)
H180.4608570.2840090.170680.034*
C190.3157 (4)0.2666 (4)0.26000 (14)0.0260 (6)
H190.1814350.3207780.2454630.031*
C140.3453 (4)0.2085 (4)0.32571 (13)0.0203 (5)
C130.1619 (4)0.2201 (4)0.37000 (13)0.0213 (5)
H13A0.1276620.1030630.3613790.026*
H13B0.0435020.3397150.3599340.026*
O40.2023 (3)0.2276 (3)0.43867 (9)0.0223 (4)
C100.0431 (4)0.2479 (4)0.48386 (13)0.0194 (5)
C110.1494 (4)0.2620 (4)0.46717 (13)0.0213 (5)
H110.1755530.2524390.4218650.026*
C120.3018 (4)0.2899 (4)0.51696 (13)0.0210 (5)
H120.4326760.2995540.5051040.025*
C70.2699 (4)0.3043 (4)0.58428 (13)0.0194 (5)
C80.0735 (4)0.2877 (4)0.60019 (13)0.0216 (5)
H80.0462210.295280.6454850.026*
C90.0792 (4)0.2605 (4)0.55092 (13)0.0213 (5)
H90.2104110.2502420.5625410.026*
C60.4399 (4)0.3355 (4)0.63310 (13)0.0198 (5)
H60.5703510.3846190.6156150.024*
C50.4425 (4)0.3061 (4)0.69873 (13)0.0193 (5)
C40.6366 (4)0.3363 (4)0.73803 (13)0.0206 (5)
N30.5993 (3)0.2715 (3)0.80303 (11)0.0211 (5)
C20.3988 (4)0.1923 (4)0.81760 (14)0.0234 (6)
O10.8068 (3)0.4047 (3)0.71817 (10)0.0261 (4)
C200.7713 (4)0.2794 (4)0.84963 (14)0.0244 (6)
H20A0.8698890.2436290.8252170.029*
H20B0.7201190.1807720.8844760.029*
C210.8805 (4)0.4836 (4)0.88272 (14)0.0249 (6)
H21A0.9155140.5843210.8478930.03*
H21B1.0094820.4888590.9063170.03*
C220.7508 (5)0.5341 (4)0.93241 (15)0.0291 (6)
H22A0.6202110.5261810.9093480.035*
H22B0.7195360.4367310.9683070.035*
C230.8616 (5)0.7380 (4)0.96212 (14)0.0270 (6)
O21.0192 (3)0.7812 (3)0.99848 (11)0.0337 (5)
O30.7776 (3)0.8651 (3)0.94574 (11)0.0345 (5)
H30.8485340.976170.9633220.052*
S10.23874 (10)0.20742 (11)0.74966 (3)0.02378 (17)
S20.30627 (13)0.09347 (13)0.88742 (4)0.0364 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C150.0221 (14)0.0231 (14)0.0265 (14)0.0092 (11)0.0012 (11)0.0007 (11)
C160.0182 (14)0.0280 (15)0.0378 (17)0.0095 (12)0.0002 (11)0.0040 (12)
C170.0259 (15)0.0265 (15)0.0339 (16)0.0145 (12)0.0084 (12)0.0038 (12)
C180.0327 (16)0.0268 (15)0.0259 (15)0.0123 (13)0.0020 (12)0.0039 (11)
C190.0219 (14)0.0256 (15)0.0301 (15)0.0082 (12)0.0036 (11)0.0050 (11)
C140.0191 (13)0.0167 (12)0.0255 (14)0.0075 (10)0.0003 (10)0.0009 (10)
C130.0179 (13)0.0234 (14)0.0231 (13)0.0084 (11)0.0011 (10)0.0012 (10)
O40.0175 (9)0.0281 (10)0.0228 (10)0.0104 (8)0.0006 (7)0.0037 (8)
C100.0180 (13)0.0147 (12)0.0256 (14)0.0066 (10)0.0003 (10)0.0034 (10)
C110.0201 (13)0.0223 (14)0.0226 (13)0.0090 (11)0.0025 (10)0.0035 (10)
C120.0159 (13)0.0221 (13)0.0265 (14)0.0087 (11)0.0029 (10)0.0026 (10)
C70.0189 (13)0.0144 (12)0.0249 (13)0.0063 (10)0.0019 (10)0.0029 (10)
C80.0262 (14)0.0186 (13)0.0221 (13)0.0103 (11)0.0055 (11)0.0043 (10)
C90.0185 (13)0.0210 (13)0.0268 (14)0.0096 (11)0.0039 (10)0.0043 (10)
C60.0140 (12)0.0183 (13)0.0277 (14)0.0066 (10)0.0028 (10)0.0009 (10)
C50.0158 (12)0.0176 (12)0.0253 (13)0.0073 (10)0.0018 (10)0.0000 (10)
C40.0202 (13)0.0207 (13)0.0228 (13)0.0101 (11)0.0001 (10)0.0011 (10)
N30.0194 (11)0.0221 (12)0.0231 (12)0.0094 (9)0.0003 (9)0.0018 (9)
C20.0230 (14)0.0215 (14)0.0259 (14)0.0086 (11)0.0021 (11)0.0010 (11)
O10.0186 (10)0.0307 (11)0.0289 (11)0.0090 (8)0.0029 (8)0.0021 (8)
C200.0235 (14)0.0264 (15)0.0249 (14)0.0122 (12)0.0032 (11)0.0005 (11)
C210.0231 (14)0.0253 (15)0.0251 (14)0.0084 (12)0.0023 (11)0.0005 (11)
C220.0279 (16)0.0250 (15)0.0314 (16)0.0067 (12)0.0007 (12)0.0002 (12)
C230.0307 (16)0.0296 (15)0.0223 (14)0.0129 (13)0.0032 (11)0.0026 (11)
O20.0376 (13)0.0294 (12)0.0346 (12)0.0153 (10)0.0108 (9)0.0017 (9)
O30.0397 (13)0.0289 (12)0.0364 (12)0.0166 (10)0.0090 (10)0.0024 (9)
S10.0171 (3)0.0277 (4)0.0256 (4)0.0073 (3)0.0027 (2)0.0015 (3)
S20.0334 (4)0.0437 (5)0.0266 (4)0.0073 (4)0.0078 (3)0.0078 (3)
Geometric parameters (Å, º) top
C15—H150.95C8—C91.376 (4)
C15—C161.390 (4)C9—H90.95
C15—C141.385 (4)C6—H60.95
C16—H160.95C6—C51.338 (4)
C16—C171.384 (4)C5—C41.483 (4)
C17—H170.95C5—S11.752 (3)
C17—C181.387 (4)C4—N31.399 (3)
C18—H180.95C4—O11.215 (3)
C18—C191.394 (4)N3—C21.371 (3)
C19—H190.95N3—C201.473 (3)
C19—C141.394 (4)C2—S11.750 (3)
C14—C131.503 (4)C2—S21.641 (3)
C13—H13A0.99C20—H20A0.99
C13—H13B0.99C20—H20B0.99
C13—O41.435 (3)C20—C211.526 (4)
O4—C101.365 (3)C21—H21A0.99
C10—C111.393 (4)C21—H21B0.99
C10—C91.399 (4)C21—C221.535 (4)
C11—H110.95C22—H22A0.99
C11—C121.381 (4)C22—H22B0.99
C12—H120.95C22—C231.500 (4)
C12—C71.398 (4)C23—O21.230 (3)
C7—C81.410 (4)C23—O31.310 (3)
C7—C61.453 (4)O3—H30.84
C8—H80.95
C16—C15—H15119.9C8—C9—C10120.7 (2)
C14—C15—H15119.9C8—C9—H9119.7
C14—C15—C16120.2 (3)C7—C6—H6114.8
C15—C16—H16119.6C5—C6—C7130.5 (2)
C17—C16—C15120.9 (3)C5—C6—H6114.8
C17—C16—H16119.6C6—C5—C4120.7 (2)
C16—C17—H17120.4C6—C5—S1129.6 (2)
C16—C17—C18119.2 (3)C4—C5—S1109.39 (19)
C18—C17—H17120.4N3—C4—C5110.6 (2)
C17—C18—H18119.9O1—C4—C5126.5 (2)
C17—C18—C19120.2 (3)O1—C4—N3123.0 (2)
C19—C18—H18119.9C4—N3—C20119.4 (2)
C18—C19—H19119.8C2—N3—C4116.3 (2)
C18—C19—C14120.4 (3)C2—N3—C20124.1 (2)
C14—C19—H19119.8N3—C2—S1110.90 (19)
C15—C14—C19119.2 (3)N3—C2—S2127.8 (2)
C15—C14—C13122.7 (2)S2—C2—S1121.31 (17)
C19—C14—C13118.0 (2)N3—C20—H20A109.1
C14—C13—H13A109.6N3—C20—H20B109.1
C14—C13—H13B109.6N3—C20—C21112.3 (2)
H13A—C13—H13B108.1H20A—C20—H20B107.9
O4—C13—C14110.2 (2)C21—C20—H20A109.1
O4—C13—H13A109.6C21—C20—H20B109.1
O4—C13—H13B109.6C20—C21—H21A109.1
C10—O4—C13115.7 (2)C20—C21—H21B109.1
O4—C10—C11124.4 (2)C20—C21—C22112.6 (2)
O4—C10—C9116.2 (2)H21A—C21—H21B107.8
C11—C10—C9119.4 (2)C22—C21—H21A109.1
C10—C11—H11120.2C22—C21—H21B109.1
C12—C11—C10119.5 (2)C21—C22—H22A109.5
C12—C11—H11120.2C21—C22—H22B109.5
C11—C12—H12118.9H22A—C22—H22B108.1
C11—C12—C7122.1 (2)C23—C22—C21110.7 (2)
C7—C12—H12118.9C23—C22—H22A109.5
C12—C7—C8117.5 (2)C23—C22—H22B109.5
C12—C7—C6118.2 (2)O2—C23—C22122.3 (3)
C8—C7—C6124.3 (2)O2—C23—O3123.2 (3)
C7—C8—H8119.6O3—C23—C22114.5 (3)
C9—C8—C7120.8 (2)C23—O3—H3109.5
C9—C8—H8119.6C2—S1—C592.66 (13)
C10—C9—H9119.7
C15—C16—C17—C181.1 (4)C9—C10—C11—C120.6 (4)
C15—C14—C13—O425.0 (4)C6—C7—C8—C9179.2 (2)
C16—C15—C14—C190.5 (4)C6—C5—C4—N3171.9 (2)
C16—C15—C14—C13175.9 (3)C6—C5—C4—O17.1 (4)
C16—C17—C18—C190.4 (4)C6—C5—S1—C2169.8 (3)
C17—C18—C19—C140.7 (4)C5—C4—N3—C21.1 (3)
C18—C19—C14—C151.1 (4)C5—C4—N3—C20177.1 (2)
C18—C19—C14—C13175.4 (3)C4—C5—S1—C23.3 (2)
C19—C14—C13—O4158.6 (2)C4—N3—C2—S13.6 (3)
C14—C15—C16—C170.7 (4)C4—N3—C2—S2176.4 (2)
C14—C13—O4—C10177.0 (2)C4—N3—C20—C2183.1 (3)
C13—O4—C10—C110.3 (4)N3—C2—S1—C53.9 (2)
C13—O4—C10—C9178.4 (2)N3—C20—C21—C2269.9 (3)
O4—C10—C11—C12177.5 (2)C2—N3—C20—C21101.2 (3)
O4—C10—C9—C8177.9 (2)O1—C4—N3—C2178.0 (3)
C10—C11—C12—C70.1 (4)O1—C4—N3—C202.0 (4)
C11—C10—C9—C80.4 (4)C20—N3—C2—S1179.39 (19)
C11—C12—C7—C80.5 (4)C20—N3—C2—S20.6 (4)
C11—C12—C7—C6179.4 (2)C20—C21—C22—C23178.3 (2)
C12—C7—C8—C90.7 (4)C21—C22—C23—O265.8 (4)
C12—C7—C6—C5161.1 (3)C21—C22—C23—O3113.7 (3)
C7—C8—C9—C100.3 (4)S1—C5—C4—N31.9 (3)
C7—C6—C5—C4175.8 (3)S1—C5—C4—O1179.0 (2)
C7—C6—C5—S13.4 (4)S2—C2—S1—C5176.08 (18)
C8—C7—C6—C518.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.841.812.645 (3)175
C13—H13B···O1ii0.992.63.522 (3)155
C13—H13A···S1iii0.993.033.792 (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
C22H16N2OS2Z = 4
Mr = 388.49F(000) = 808
Triclinic, P1Dx = 1.348 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.5325 (5) ÅCell parameters from 8383 reflections
b = 12.8492 (6) Åθ = 3.2–28.6°
c = 13.6465 (7) ŵ = 0.29 mm1
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 Source6679 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.046
Detector resolution: 10.3756 pixels mm-1θmax = 28.7°, θmin = 3.0°
ω scansh = 1616
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
k = 1717
Tmin = 0.456, Tmax = 1l = 1818
25766 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.0505P)2 + 3.5362P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
8981 reflectionsΔρmax = 0.47 e Å3
487 parametersΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
C2D0.2202 (2)0.5767 (3)0.6587 (2)0.0263 (6)
N3D0.2167 (2)0.5261 (2)0.56519 (17)0.0248 (5)
H3D0.2833270.5489450.5353120.03*
C4D0.1058 (2)0.4379 (3)0.5182 (2)0.0243 (6)
C5D0.0094 (2)0.4180 (3)0.5835 (2)0.0235 (6)
O1D0.09290 (17)0.38515 (18)0.43481 (15)0.0278 (4)
C6D0.1064 (2)0.3335 (2)0.5537 (2)0.0239 (6)
H6D0.1188370.2954310.487320.029*
C7D0.2151 (2)0.2900 (3)0.6037 (2)0.0238 (6)
C12D0.3220 (3)0.1927 (3)0.5529 (2)0.0266 (6)
H12D0.3205680.1618460.4867170.032*
C11D0.4280 (3)0.1415 (3)0.5961 (2)0.0268 (6)
H11D0.4983030.0759780.5595410.032*
C10D0.4343 (2)0.1843 (2)0.6937 (2)0.0235 (6)
C9D0.3292 (2)0.2841 (3)0.7446 (2)0.0254 (6)
H9D0.3315310.3167470.8099670.03*
C8D0.2226 (2)0.3347 (3)0.6999 (2)0.0246 (6)
H8D0.1527210.4015970.7355310.029*
N1D0.5400 (2)0.1299 (2)0.73885 (17)0.0264 (5)
C19D0.5430 (2)0.1542 (3)0.8434 (2)0.0255 (6)
C24D0.6266 (3)0.1896 (3)0.8755 (2)0.0312 (7)
H24D0.6772430.2003260.8283680.037*
C23D0.6360 (3)0.2091 (3)0.9758 (2)0.0375 (7)
H23D0.6936180.2323980.9973920.045*
C22D0.5620 (3)0.1947 (3)1.0440 (2)0.0418 (8)
H22D0.567510.2095561.1128820.05*
C21D0.4793 (3)0.1584 (3)1.0125 (2)0.0424 (8)
H21D0.4291550.1472621.0598480.051*
C20D0.4696 (3)0.1385 (3)0.9121 (2)0.0340 (7)
H20D0.4126190.1141430.8906670.041*
C13D0.6560 (2)0.0516 (3)0.6829 (2)0.0258 (6)
C18D0.6963 (3)0.0843 (3)0.6012 (2)0.0283 (6)
H18D0.6446070.1564110.577420.034*
C17D0.8139 (3)0.0094 (3)0.5547 (2)0.0323 (7)
H17D0.8423550.0302610.4983790.039*
C16D0.8893 (3)0.0951 (3)0.5900 (2)0.0321 (7)
H16D0.9700740.1442460.5591330.039*
C15D0.8480 (3)0.1280 (3)0.6695 (2)0.0337 (7)
H15D0.8999160.1998280.6936220.04*
C14D0.7299 (3)0.0557 (3)0.7146 (2)0.0310 (7)
H14D0.6998390.0802830.7674920.037*
C2E0.2852 (3)0.4244 (3)0.2151 (2)0.0323 (7)
N3E0.2866 (2)0.4495 (2)0.31424 (18)0.0286 (5)
H3E0.2183750.4241340.3420350.034*
C4E0.3981 (2)0.5159 (3)0.3707 (2)0.0256 (6)
C5E0.4966 (3)0.5408 (3)0.3068 (2)0.0266 (6)
O1E0.41003 (18)0.5491 (2)0.45980 (16)0.0341 (5)
C6E0.6128 (3)0.6054 (3)0.3471 (2)0.0263 (6)
H6E0.6217040.6223940.4174540.032*
C7E0.7268 (2)0.6541 (3)0.3045 (2)0.0252 (6)
C12E0.8312 (3)0.7363 (3)0.3675 (2)0.0261 (6)
H12E0.8249070.7501890.4363110.031*
C11E0.9422 (3)0.7975 (3)0.3330 (2)0.0276 (6)
H11E1.0114180.851810.37780.033*
C10E0.9534 (3)0.7801 (3)0.2317 (2)0.0265 (6)
C9E0.8512 (3)0.6942 (3)0.1683 (2)0.0285 (6)
H9E0.8583810.6781230.0999420.034*
C8E0.7399 (3)0.6324 (3)0.2044 (2)0.0279 (6)
H8E0.6715770.5745860.1603630.033*
N1E1.0654 (2)0.8479 (2)0.19763 (19)0.0303 (6)
C19E1.0953 (3)0.8144 (3)0.1044 (2)0.0313 (7)
C20E1.0814 (3)0.7019 (3)0.0774 (2)0.0360 (7)
H20E1.0487870.6437620.1206590.043*
C21E1.1152 (3)0.6735 (3)0.0131 (3)0.0432 (9)
H21E1.1048990.5956580.032280.052*
C22E1.1640 (3)0.7588 (4)0.0750 (3)0.0513 (10)
H22E1.1881810.7400570.1365870.062*
C23E1.1774 (4)0.8705 (4)0.0476 (3)0.0582 (11)
H23E1.2102230.92860.0907630.07*
C24E1.1439 (3)0.8993 (3)0.0415 (3)0.0466 (9)
H24E1.1540250.9771580.0599710.056*
C13E1.1495 (3)0.9622 (3)0.2516 (2)0.0294 (6)
C18E1.1156 (3)1.0487 (3)0.2772 (3)0.0362 (7)
H18E1.0339881.0316730.2605780.043*
C17E1.1993 (3)1.1594 (3)0.3267 (3)0.0444 (9)
H17E1.1751941.2183560.3439550.053*
C16E1.3193 (3)1.1853 (3)0.3515 (3)0.0442 (9)
H16E1.3772491.2617060.3853180.053*
C15E1.3530 (3)1.0988 (3)0.3263 (3)0.0416 (8)
H15E1.4345991.1158790.3429750.05*
C14E1.2692 (3)0.9876 (3)0.2770 (2)0.0342 (7)
H14E1.2931250.9284320.260470.041*
S1D0.07352 (6)0.51434 (7)0.69619 (5)0.02786 (17)
S2D0.34175 (7)0.67997 (8)0.72782 (6)0.0394 (2)
S1E0.43463 (7)0.48156 (8)0.18354 (6)0.0338 (2)
S2E0.16332 (8)0.35314 (10)0.13556 (7)0.0501 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2D0.0182 (13)0.0292 (15)0.0302 (15)0.0098 (11)0.0048 (11)0.0060 (12)
N3D0.0151 (11)0.0299 (13)0.0269 (12)0.0085 (10)0.0062 (9)0.0039 (10)
C4D0.0172 (13)0.0267 (14)0.0298 (14)0.0105 (11)0.0054 (11)0.0067 (12)
C5D0.0180 (13)0.0275 (14)0.0261 (14)0.0114 (11)0.0057 (11)0.0041 (11)
O1D0.0186 (9)0.0327 (11)0.0288 (11)0.0101 (8)0.0056 (8)0.0012 (9)
C6D0.0203 (13)0.0254 (14)0.0270 (14)0.0114 (11)0.0059 (11)0.0043 (11)
C7D0.0152 (12)0.0267 (14)0.0289 (14)0.0095 (11)0.0038 (11)0.0045 (11)
C12D0.0226 (14)0.0309 (15)0.0243 (14)0.0121 (12)0.0040 (11)0.0005 (12)
C11D0.0188 (13)0.0284 (15)0.0279 (14)0.0080 (11)0.0027 (11)0.0002 (12)
C10D0.0180 (13)0.0261 (14)0.0268 (14)0.0103 (11)0.0054 (11)0.0064 (11)
C9D0.0217 (13)0.0273 (14)0.0258 (14)0.0111 (12)0.0038 (11)0.0009 (11)
C8D0.0185 (13)0.0252 (14)0.0261 (14)0.0076 (11)0.0029 (11)0.0020 (11)
N1D0.0173 (11)0.0326 (13)0.0249 (12)0.0084 (10)0.0045 (9)0.0031 (10)
C19D0.0184 (13)0.0271 (14)0.0248 (14)0.0059 (11)0.0053 (11)0.0034 (11)
C24D0.0292 (15)0.0347 (16)0.0309 (15)0.0167 (13)0.0039 (12)0.0030 (13)
C23D0.0346 (17)0.0440 (19)0.0350 (17)0.0204 (15)0.0093 (14)0.0001 (14)
C22D0.0388 (18)0.054 (2)0.0251 (15)0.0175 (17)0.0087 (14)0.0001 (15)
C21D0.0355 (18)0.059 (2)0.0306 (17)0.0216 (17)0.0003 (14)0.0075 (16)
C20D0.0251 (15)0.0453 (19)0.0341 (16)0.0181 (14)0.0067 (13)0.0079 (14)
C13D0.0171 (13)0.0305 (15)0.0263 (14)0.0096 (11)0.0050 (11)0.0015 (12)
C18D0.0235 (14)0.0292 (15)0.0309 (15)0.0119 (12)0.0038 (12)0.0026 (12)
C17D0.0274 (15)0.0358 (17)0.0351 (16)0.0179 (13)0.0001 (13)0.0012 (13)
C16D0.0200 (14)0.0354 (17)0.0341 (16)0.0100 (13)0.0014 (12)0.0057 (13)
C15D0.0259 (15)0.0317 (16)0.0331 (16)0.0058 (13)0.0081 (13)0.0016 (13)
C14D0.0280 (15)0.0358 (17)0.0242 (14)0.0111 (13)0.0064 (12)0.0032 (12)
C2E0.0238 (15)0.0334 (16)0.0374 (17)0.0120 (13)0.0059 (12)0.0034 (13)
N3E0.0175 (11)0.0323 (13)0.0339 (13)0.0103 (10)0.0082 (10)0.0035 (11)
C4E0.0194 (13)0.0291 (15)0.0322 (15)0.0135 (12)0.0073 (11)0.0087 (12)
C5E0.0233 (14)0.0318 (15)0.0277 (14)0.0147 (12)0.0092 (11)0.0065 (12)
O1E0.0213 (10)0.0503 (14)0.0297 (11)0.0162 (10)0.0077 (9)0.0045 (10)
C6E0.0249 (14)0.0334 (15)0.0255 (14)0.0167 (12)0.0088 (11)0.0078 (12)
C7E0.0195 (13)0.0277 (14)0.0299 (14)0.0117 (11)0.0065 (11)0.0069 (12)
C12E0.0239 (14)0.0310 (15)0.0259 (14)0.0143 (12)0.0078 (11)0.0059 (12)
C11E0.0192 (13)0.0306 (15)0.0310 (15)0.0102 (12)0.0035 (11)0.0044 (12)
C10E0.0220 (14)0.0315 (15)0.0293 (15)0.0143 (12)0.0076 (11)0.0087 (12)
C9E0.0236 (14)0.0380 (17)0.0255 (14)0.0158 (13)0.0053 (11)0.0047 (12)
C8E0.0211 (14)0.0320 (15)0.0302 (15)0.0128 (12)0.0018 (11)0.0034 (12)
N1E0.0227 (12)0.0335 (14)0.0315 (13)0.0105 (11)0.0096 (10)0.0041 (11)
C19E0.0194 (14)0.0406 (17)0.0306 (15)0.0120 (13)0.0055 (12)0.0028 (13)
C20E0.0259 (15)0.0463 (19)0.0344 (17)0.0175 (14)0.0016 (13)0.0000 (14)
C21E0.0276 (17)0.051 (2)0.045 (2)0.0173 (16)0.0010 (14)0.0099 (16)
C22E0.0322 (18)0.064 (3)0.041 (2)0.0113 (18)0.0161 (15)0.0055 (18)
C23E0.056 (2)0.058 (3)0.040 (2)0.010 (2)0.0202 (18)0.0065 (19)
C24E0.047 (2)0.043 (2)0.0411 (19)0.0142 (17)0.0156 (16)0.0071 (16)
C13E0.0266 (15)0.0297 (15)0.0304 (15)0.0111 (12)0.0104 (12)0.0071 (12)
C18E0.0327 (17)0.0374 (18)0.0435 (19)0.0196 (14)0.0123 (14)0.0090 (15)
C17E0.048 (2)0.0304 (17)0.055 (2)0.0168 (16)0.0197 (17)0.0110 (16)
C16E0.043 (2)0.0298 (17)0.0432 (19)0.0030 (15)0.0112 (16)0.0051 (15)
C15E0.0268 (16)0.0427 (19)0.0428 (19)0.0058 (14)0.0056 (14)0.0096 (16)
C14E0.0265 (15)0.0375 (17)0.0407 (18)0.0156 (14)0.0107 (13)0.0101 (14)
S1D0.0186 (3)0.0335 (4)0.0268 (4)0.0094 (3)0.0047 (3)0.0000 (3)
S2D0.0209 (4)0.0441 (5)0.0387 (4)0.0070 (3)0.0016 (3)0.0088 (4)
S1E0.0223 (4)0.0436 (5)0.0298 (4)0.0119 (3)0.0066 (3)0.0003 (3)
S2E0.0250 (4)0.0709 (7)0.0384 (5)0.0133 (4)0.0004 (3)0.0058 (4)
Geometric parameters (Å, º) top
C2D—N3D1.355 (4)C2E—N3E1.353 (4)
C2D—S2D1.632 (3)C2E—S2E1.632 (3)
C2D—S1D1.751 (3)C2E—S1E1.754 (3)
N3D—C4D1.380 (3)N3E—C4E1.382 (4)
N3D—H3D0.88N3E—H3E0.88
C4D—O1D1.221 (3)C4E—O1E1.221 (3)
C4D—C5D1.473 (4)C4E—C5E1.473 (4)
C5D—C6D1.347 (4)C5E—C6E1.342 (4)
C5D—S1D1.754 (3)C5E—S1E1.749 (3)
C6D—C7D1.442 (4)C6E—C7E1.442 (4)
C6D—H6D0.95C6E—H6E0.95
C7D—C8D1.400 (4)C7E—C8E1.397 (4)
C7D—C12D1.409 (4)C7E—C12E1.402 (4)
C12D—C11D1.369 (4)C12E—C11E1.372 (4)
C12D—H12D0.95C12E—H12E0.95
C11D—C10D1.403 (4)C11E—C10E1.399 (4)
C11D—H11D0.95C11E—H11E0.95
C10D—N1D1.384 (3)C10E—N1E1.393 (4)
C10D—C9D1.412 (4)C10E—C9E1.402 (4)
C9D—C8D1.385 (4)C9E—C8E1.385 (4)
C9D—H9D0.95C9E—H9E0.95
C8D—H8D0.95C8E—H8E0.95
N1D—C19D1.433 (4)N1E—C19E1.420 (4)
N1D—C13D1.436 (4)N1E—C13E1.430 (4)
C19D—C20D1.381 (4)C19E—C20E1.377 (5)
C19D—C24D1.392 (4)C19E—C24E1.387 (5)
C24D—C23D1.385 (4)C20E—C21E1.389 (5)
C24D—H24D0.95C20E—H20E0.95
C23D—C22D1.373 (5)C21E—C22E1.381 (6)
C23D—H23D0.95C21E—H21E0.95
C22D—C21D1.389 (5)C22E—C23E1.369 (6)
C22D—H22D0.95C22E—H22E0.95
C21D—C20D1.387 (4)C23E—C24E1.372 (5)
C21D—H21D0.95C23E—H23E0.95
C20D—H20D0.95C24E—H24E0.95
C13D—C14D1.381 (4)C13E—C18E1.382 (4)
C13D—C18D1.389 (4)C13E—C14E1.395 (4)
C18D—C17D1.395 (4)C18E—C17E1.378 (5)
C18D—H18D0.95C18E—H18E0.95
C17D—C16D1.383 (5)C17E—C16E1.395 (5)
C17D—H17D0.95C17E—H17E0.95
C16D—C15D1.372 (5)C16E—C15E1.379 (5)
C16D—H16D0.95C16E—H16E0.95
C15D—C14D1.388 (4)C15E—C14E1.380 (5)
C15D—H15D0.95C15E—H15E0.95
C14D—H14D0.95C14E—H14E0.95
N3D—C2D—S2D125.9 (2)N3E—C2E—S1E109.9 (2)
N3D—C2D—S1D110.0 (2)S2E—C2E—S1E124.54 (19)
S2D—C2D—S1D124.14 (18)C2E—N3E—C4E118.3 (2)
C2D—N3D—C4D118.1 (2)C2E—N3E—H3E120.9
C2D—N3D—H3D120.9C4E—N3E—H3E120.9
C4D—N3D—H3D120.9O1E—C4E—N3E123.8 (2)
O1D—C4D—N3D123.4 (2)O1E—C4E—C5E126.6 (3)
O1D—C4D—C5D126.5 (3)N3E—C4E—C5E109.6 (2)
N3D—C4D—C5D110.1 (2)C6E—C5E—C4E119.3 (3)
C6D—C5D—C4D120.4 (3)C6E—C5E—S1E130.9 (2)
C6D—C5D—S1D130.2 (2)C4E—C5E—S1E109.8 (2)
C4D—C5D—S1D109.4 (2)C5E—C6E—C7E132.5 (3)
C5D—C6D—C7D132.1 (3)C5E—C6E—H6E113.7
C5D—C6D—H6D113.9C7E—C6E—H6E113.7
C7D—C6D—H6D113.9C8E—C7E—C12E117.6 (3)
C8D—C7D—C12D117.0 (2)C8E—C7E—C6E125.2 (3)
C8D—C7D—C6D125.3 (3)C12E—C7E—C6E117.1 (3)
C12D—C7D—C6D117.7 (3)C11E—C12E—C7E122.1 (3)
C11D—C12D—C7D121.9 (3)C11E—C12E—H12E118.9
C11D—C12D—H12D119C7E—C12E—H12E118.9
C7D—C12D—H12D119C12E—C11E—C10E120.0 (3)
C12D—C11D—C10D120.9 (3)C12E—C11E—H11E120
C12D—C11D—H11D119.5C10E—C11E—H11E120
C10D—C11D—H11D119.5N1E—C10E—C11E119.0 (3)
N1D—C10D—C11D121.1 (2)N1E—C10E—C9E122.4 (3)
N1D—C10D—C9D121.0 (2)C11E—C10E—C9E118.6 (3)
C11D—C10D—C9D117.9 (2)C8E—C9E—C10E120.6 (3)
C8D—C9D—C10D120.3 (3)C8E—C9E—H9E119.7
C8D—C9D—H9D119.8C10E—C9E—H9E119.7
C10D—C9D—H9D119.8C9E—C8E—C7E120.9 (3)
C9D—C8D—C7D121.8 (3)C9E—C8E—H8E119.5
C9D—C8D—H8D119.1C7E—C8E—H8E119.5
C7D—C8D—H8D119.1C10E—N1E—C19E122.4 (3)
C10D—N1D—C19D122.5 (2)C10E—N1E—C13E119.9 (2)
C10D—N1D—C13D122.0 (2)C19E—N1E—C13E117.3 (2)
C19D—N1D—C13D115.3 (2)C20E—C19E—C24E119.9 (3)
C20D—C19D—C24D119.7 (3)C20E—C19E—N1E121.4 (3)
C20D—C19D—N1D121.9 (3)C24E—C19E—N1E118.6 (3)
C24D—C19D—N1D118.3 (3)C19E—C20E—C21E119.8 (3)
C23D—C24D—C19D120.2 (3)C19E—C20E—H20E120.1
C23D—C24D—H24D119.9C21E—C20E—H20E120.1
C19D—C24D—H24D119.9C22E—C21E—C20E119.8 (4)
C22D—C23D—C24D120.0 (3)C22E—C21E—H21E120.1
C22D—C23D—H23D120C20E—C21E—H21E120.1
C24D—C23D—H23D120C23E—C22E—C21E119.9 (3)
C23D—C22D—C21D120.1 (3)C23E—C22E—H22E120
C23D—C22D—H22D120C21E—C22E—H22E120
C21D—C22D—H22D120C22E—C23E—C24E120.7 (4)
C20D—C21D—C22D120.2 (3)C22E—C23E—H23E119.6
C20D—C21D—H21D119.9C24E—C23E—H23E119.6
C22D—C21D—H21D119.9C23E—C24E—C19E119.8 (4)
C19D—C20D—C21D119.8 (3)C23E—C24E—H24E120.1
C19D—C20D—H20D120.1C19E—C24E—H24E120.1
C21D—C20D—H20D120.1C18E—C13E—C14E119.4 (3)
C14D—C13D—C18D120.1 (3)C18E—C13E—N1E121.6 (3)
C14D—C13D—N1D118.6 (3)C14E—C13E—N1E119.0 (3)
C18D—C13D—N1D121.3 (3)C17E—C18E—C13E120.4 (3)
C13D—C18D—C17D118.9 (3)C17E—C18E—H18E119.8
C13D—C18D—H18D120.6C13E—C18E—H18E119.8
C17D—C18D—H18D120.6C18E—C17E—C16E120.2 (3)
C16D—C17D—C18D120.5 (3)C18E—C17E—H17E119.9
C16D—C17D—H17D119.8C16E—C17E—H17E119.9
C18D—C17D—H17D119.8C15E—C16E—C17E119.3 (3)
C15D—C16D—C17D120.3 (3)C15E—C16E—H16E120.3
C15D—C16D—H16D119.8C17E—C16E—H16E120.3
C17D—C16D—H16D119.8C16E—C15E—C14E120.6 (3)
C16D—C15D—C14D119.6 (3)C16E—C15E—H15E119.7
C16D—C15D—H15D120.2C14E—C15E—H15E119.7
C14D—C15D—H15D120.2C15E—C14E—C13E120.0 (3)
C13D—C14D—C15D120.4 (3)C15E—C14E—H14E120
C13D—C14D—H14D119.8C13E—C14E—H14E120
C15D—C14D—H14D119.8C2D—S1D—C5D92.48 (13)
N3E—C2E—S2E125.6 (2)C5E—S1E—C2E92.34 (14)
S2D—C2D—N3D—C4D178.7 (2)O1E—C4E—C5E—C6E0.5 (5)
S1D—C2D—N3D—C4D1.1 (3)N3E—C4E—C5E—C6E179.5 (3)
C2D—N3D—C4D—O1D178.6 (3)O1E—C4E—C5E—S1E176.7 (3)
C2D—N3D—C4D—C5D0.8 (4)N3E—C4E—C5E—S1E2.2 (3)
O1D—C4D—C5D—C6D1.0 (5)C4E—C5E—C6E—C7E173.0 (3)
N3D—C4D—C5D—C6D178.4 (3)S1E—C5E—C6E—C7E3.6 (5)
O1D—C4D—C5D—S1D179.2 (3)C5E—C6E—C7E—C8E6.6 (5)
N3D—C4D—C5D—S1D0.2 (3)C5E—C6E—C7E—C12E168.5 (3)
C4D—C5D—C6D—C7D175.1 (3)C8E—C7E—C12E—C11E2.3 (4)
S1D—C5D—C6D—C7D2.7 (5)C6E—C7E—C12E—C11E173.1 (3)
C5D—C6D—C7D—C8D3.1 (5)C7E—C12E—C11E—C10E1.0 (5)
C5D—C6D—C7D—C12D175.3 (3)C12E—C11E—C10E—N1E176.6 (3)
C8D—C7D—C12D—C11D1.9 (4)C12E—C11E—C10E—C9E3.8 (4)
C6D—C7D—C12D—C11D176.7 (3)N1E—C10E—C9E—C8E177.0 (3)
C7D—C12D—C11D—C10D0.1 (5)C11E—C10E—C9E—C8E3.4 (4)
C12D—C11D—C10D—N1D177.5 (3)C10E—C9E—C8E—C7E0.1 (5)
C12D—C11D—C10D—C9D1.9 (4)C12E—C7E—C8E—C9E2.7 (4)
N1D—C10D—C9D—C8D177.4 (3)C6E—C7E—C8E—C9E172.3 (3)
C11D—C10D—C9D—C8D2.1 (4)C11E—C10E—N1E—C19E161.6 (3)
C10D—C9D—C8D—C7D0.3 (4)C9E—C10E—N1E—C19E18.0 (4)
C12D—C7D—C8D—C9D1.7 (4)C11E—C10E—N1E—C13E25.7 (4)
C6D—C7D—C8D—C9D176.7 (3)C9E—C10E—N1E—C13E154.7 (3)
C11D—C10D—N1D—C19D166.6 (3)C10E—N1E—C19E—C20E51.5 (4)
C9D—C10D—N1D—C19D12.9 (4)C13E—N1E—C19E—C20E135.7 (3)
C11D—C10D—N1D—C13D18.1 (4)C10E—N1E—C19E—C24E131.1 (3)
C9D—C10D—N1D—C13D162.5 (3)C13E—N1E—C19E—C24E41.8 (4)
C10D—N1D—C19D—C20D56.9 (4)C24E—C19E—C20E—C21E0.5 (5)
C13D—N1D—C19D—C20D127.5 (3)N1E—C19E—C20E—C21E178.0 (3)
C10D—N1D—C19D—C24D126.0 (3)C19E—C20E—C21E—C22E0.8 (5)
C13D—N1D—C19D—C24D49.6 (4)C20E—C21E—C22E—C23E0.8 (6)
C20D—C19D—C24D—C23D0.1 (5)C21E—C22E—C23E—C24E0.6 (6)
N1D—C19D—C24D—C23D177.3 (3)C22E—C23E—C24E—C19E0.4 (6)
C19D—C24D—C23D—C22D0.6 (5)C20E—C19E—C24E—C23E0.3 (5)
C24D—C23D—C22D—C21D1.2 (5)N1E—C19E—C24E—C23E177.8 (3)
C23D—C22D—C21D—C20D1.1 (6)C10E—N1E—C13E—C18E52.8 (4)
C24D—C19D—C20D—C21D0.2 (5)C19E—N1E—C13E—C18E120.3 (3)
N1D—C19D—C20D—C21D177.3 (3)C10E—N1E—C13E—C14E128.6 (3)
C22D—C21D—C20D—C19D0.3 (5)C19E—N1E—C13E—C14E58.3 (4)
C10D—N1D—C13D—C14D133.7 (3)C14E—C13E—C18E—C17E0.5 (5)
C19D—N1D—C13D—C14D50.6 (4)N1E—C13E—C18E—C17E178.1 (3)
C10D—N1D—C13D—C18D49.1 (4)C13E—C18E—C17E—C16E0.0 (5)
C19D—N1D—C13D—C18D126.5 (3)C18E—C17E—C16E—C15E0.3 (5)
C14D—C13D—C18D—C17D2.6 (4)C17E—C16E—C15E—C14E0.0 (5)
N1D—C13D—C18D—C17D174.5 (3)C16E—C15E—C14E—C13E0.5 (5)
C13D—C18D—C17D—C16D0.6 (4)C18E—C13E—C14E—C15E0.8 (5)
C18D—C17D—C16D—C15D1.9 (5)N1E—C13E—C14E—C15E177.9 (3)
C17D—C16D—C15D—C14D0.1 (5)N3D—C2D—S1D—C5D0.8 (2)
C18D—C13D—C14D—C15D4.5 (4)S2D—C2D—S1D—C5D179.0 (2)
N1D—C13D—C14D—C15D172.7 (3)C6D—C5D—S1D—C2D177.7 (3)
C16D—C15D—C14D—C13D3.1 (5)C4D—C5D—S1D—C2D0.3 (2)
S2E—C2E—N3E—C4E176.9 (2)C6E—C5E—S1E—C2E177.6 (3)
S1E—C2E—N3E—C4E2.5 (4)C4E—C5E—S1E—C2E0.8 (2)
C2E—N3E—C4E—O1E175.9 (3)N3E—C2E—S1E—C5E0.8 (2)
C2E—N3E—C4E—C5E3.1 (4)S2E—C2E—S1E—C5E178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3D—H3D···O1E0.881.932.784 (3)163
N3E—H3E···O1D0.881.972.836 (3)166
The interplanar angles (°) between the planes containing rings in investigated compounds 15 and other derivatives with crystal structures determined earlier, i.e. 69 Żesławska et al., 2022b; Smith et al., 2009). top
CompoundR/BR/Ph1R/Ph2B/Ph1B/Ph2Ph1/Ph2
13.22 (2)19.78 (2)-17.27 (2)--
2A: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)--
424.5 (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)
6D:18.1 (1)D:42.27 (7)-D:24.5 (1)--
E:15.7 (1)E:36.12 (8)-E:20.6 (1)--
7D: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)
96.801.63-8.11--
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
CompoundR/BR/Ph1R/Ph2B/Ph1B/Ph2Ph1/Ph2
319.742.8-41.1--
518.845.244.256.457.471.2
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.
 

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