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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, C
18H
13NO
3S
2·C
2H
6OS (
1), 4-[5-([1,1′-biphenyl]-4-ylmethylidene]-4-oxo-2-thioxothiazolidin-3-yl)butanoic acid, C
20H
17NO
3S
2 (
2), 5-[4-(benzyloxy)benzylidene]-2-thioxothiazolidin-4-one, C
17H
13NO
2S
2 (
3), 4-{5-[4-(benzyloxy)benzylidene]-4-oxo-2-thioxothiazolidin-3-yl}butanoic acid, C
21H
19NO
4S
2 (
4), and 5-[4-(diphenylamino)benzylidene]-2-thioxothiazolidin-4-one, C
22H
16N
2OS
2 (
5). Compounds
1 and
3–
5 crystallize in the triclinic space group
P, while
2 crystallizes in the monoclinic space group
P2
1/
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
CCDC references: 2284957; 2284958; 2284959; 2284960; 2284961; 2284957; 2284958
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 |
Mr = 433.54 | F(000) = 452 |
Triclinic, P1 | Dx = 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 | Rint = 0.034 |
ω scans | θmax = 51.9°, θmin = 2.5° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | h = −16→16 |
Tmin = 0.496, Tmax = 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(Fo2) + (0.0507P)2 + 0.0529P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
22177 reflections | Δρmax = 0.62 e Å−3 |
259 parameters | Δρmin = −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 | Uiso*/Ueq | |
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···O1iv | 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 |
Mr = 383.46 | Dx = 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 | Rint = 0.035 |
ω scans | θmax = 76.6°, θmin = 4.0° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | h = −6→5 |
Tmin = 0.637, Tmax = 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(Fo2) + (0.0097P)2 + 2.0556P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.076 | (Δ/σ)max = 0.001 |
S = 1.15 | Δρmax = 0.31 e Å−3 |
3746 reflections | Δρmin = −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
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 | Uiso*/Ueq | 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···O1iv | 0.99 | 2.61 | 3.509 (2) | 151 |
C6—H6···S2v | 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 |
Mr = 327.4 | F(000) = 340 |
Triclinic, P1 | Dx = 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 | Rint = 0.061 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.4°, θmin = 2.7° |
ω scans | h = −8→9 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022) | k = −13→12 |
Tmin = 0.624, Tmax = 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(Fo2) + (0.1204P)2 + 0.7354P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3370 reflections | Δρmax = 0.85 e Å−3 |
199 parameters | Δρmin = −0.86 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
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 |
Mr = 413.49 | F(000) = 432 |
Triclinic, P1 | Dx = 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 | Rint = 0.036 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.7°, θmin = 3.0° |
ω scans | h = −9→9 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | k = −9→9 |
Tmin = 0.897, Tmax = 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(Fo2) + (0.0271P)2 + 1.7628P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.001 |
4501 reflections | Δρmax = 0.38 e Å−3 |
254 parameters | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
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 |
Mr = 388.49 | F(000) = 808 |
Triclinic, P1 | Dx = 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 | Rint = 0.046 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.7°, θmin = 3.0° |
ω scans | h = −16→16 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | k = −17→17 |
Tmin = 0.456, Tmax = 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(Fo2) + (0.0505P)2 + 3.5362P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
8981 reflections | Δρmax = 0.47 e Å−3 |
487 parameters | Δρmin = −0.35 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 | Uiso*/Ueq | |
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). topCompound | 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 topCompound | 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. |
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