Buy article online - an online subscription or single-article purchase is required to access this article.
In order to determine the impact of different substituents and their positions on intermolecular interactions and ultimately on the crystal packing, unsubstituted
N-phenyl-2-phthalimidoethanesulfonamide, C
16H
14N
2O
4S, (I), and the
N-(4-nitrophenyl)-, C
16H
13N
3O
6S, (II),
N-(4-methoxyphenyl)-, C
16H
16N
3O
6S, (III), and
N-(2-ethylphenyl)-, as the monohydrate, C
18H
18N
2O
4S·H
2O, (IV), derivatives have been characterized by single-crystal X-ray crystallography. Sulfonamides (I) and (II) have triclinic crystal systems, while (III) and (IV) are monoclinic. Although the molecules differ from each other only with respect to small substituents and their positions, they crystallized in different space groups as a result of differing intra- and intermolecular hydrogen-bond interactions. The structures of (I), (II) and (III) are stabilized by intermolecular N—H
O and C—H
O hydrogen bonds, while that of (IV) is stabilized by intermolecular O—H
O and C—H
O hydrogen bonds. All four structures are of interest with respect to their biological activities and have been studied as part of a program to develop anticonvulsant drugs for the treatment of epilepsy.
Supporting information
CCDC references: 1589303; 1589302; 1589301; 1589300
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
N-Phenyl-2-phthalimidoethanesulfonamide (I)
top
Crystal data top
C16H14N2O4S | Z = 2 |
Mr = 330.35 | F(000) = 344 |
Triclinic, P1 | Dx = 1.443 Mg m−3 |
a = 6.9783 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7631 (7) Å | Cell parameters from 1691 reflections |
c = 11.8912 (9) Å | θ = 3.9–28.6° |
α = 78.365 (6)° | µ = 0.24 mm−1 |
β = 74.458 (6)° | T = 293 K |
γ = 81.063 (6)° | Needle, colourless |
V = 760.06 (10) Å3 | 0.65 × 0.20 × 0.04 mm |
Data collection top
Rigaku OD Xcalibur Eos diffractometer | 2042 reflections with I > 2σ(I) |
Detector resolution: 16.1333 pixels mm-1 | Rint = 0.017 |
ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions
derived
by Clark & Reid (1995)] | h = −8→8 |
Tmin = 0.981, Tmax = 0.998 | k = −11→11 |
5228 measured reflections | l = −14→13 |
2691 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | All H-atom parameters refined |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.1415P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2691 reflections | Δρmax = 0.22 e Å−3 |
264 parameters | Δρmin = −0.36 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 | |
S1 | 0.17173 (9) | 0.61707 (6) | 0.27867 (5) | 0.0454 (2) | |
O3 | 0.5551 (2) | 0.26502 (16) | 0.45734 (13) | 0.0525 (4) | |
O1 | −0.0169 (2) | 0.62170 (17) | 0.36395 (14) | 0.0605 (5) | |
O4 | 0.6874 (3) | 0.43478 (16) | 0.06206 (13) | 0.0580 (5) | |
N2 | 0.6061 (2) | 0.38323 (17) | 0.26525 (14) | 0.0383 (4) | |
O2 | 0.2268 (3) | 0.74129 (16) | 0.19703 (15) | 0.0634 (5) | |
N1 | 0.1816 (3) | 0.50160 (19) | 0.19698 (17) | 0.0442 (5) | |
C6 | 0.1616 (3) | 0.3564 (2) | 0.23602 (18) | 0.0374 (5) | |
C15 | 0.6942 (3) | 0.1932 (2) | 0.16803 (18) | 0.0389 (5) | |
C10 | 0.6515 (3) | 0.1420 (2) | 0.28889 (18) | 0.0381 (5) | |
C9 | 0.5980 (3) | 0.2631 (2) | 0.35246 (18) | 0.0390 (5) | |
C16 | 0.6663 (3) | 0.3489 (2) | 0.15228 (18) | 0.0407 (5) | |
C5 | 0.2178 (3) | 0.2688 (3) | 0.1518 (2) | 0.0470 (6) | |
C1 | 0.0941 (3) | 0.2995 (2) | 0.3539 (2) | 0.0469 (6) | |
C11 | 0.6608 (3) | 0.0002 (2) | 0.3317 (2) | 0.0485 (6) | |
C8 | 0.5672 (4) | 0.5260 (2) | 0.2905 (2) | 0.0469 (6) | |
C7 | 0.3544 (4) | 0.5604 (3) | 0.3617 (2) | 0.0458 (5) | |
C14 | 0.7484 (4) | 0.1044 (3) | 0.0862 (2) | 0.0545 (6) | |
C2 | 0.0904 (4) | 0.1550 (3) | 0.3863 (2) | 0.0567 (6) | |
C4 | 0.2101 (4) | 0.1253 (3) | 0.1872 (3) | 0.0550 (6) | |
C12 | 0.7156 (4) | −0.0900 (3) | 0.2492 (2) | 0.0572 (6) | |
C13 | 0.7593 (4) | −0.0386 (3) | 0.1295 (3) | 0.0613 (7) | |
C3 | 0.1488 (4) | 0.0682 (3) | 0.3038 (3) | 0.0569 (7) | |
H1 | 0.233 (3) | 0.525 (3) | 0.131 (2) | 0.049 (7)* | |
H5 | 0.270 (3) | 0.302 (2) | 0.071 (2) | 0.055 (7)* | |
H14 | 0.778 (4) | 0.138 (3) | 0.002 (2) | 0.066 (8)* | |
H1A | 0.053 (3) | 0.354 (2) | 0.409 (2) | 0.052 (7)* | |
H7A | 0.312 (3) | 0.482 (2) | 0.421 (2) | 0.048 (6)* | |
H8A | 0.604 (3) | 0.587 (2) | 0.214 (2) | 0.054 (7)* | |
H7B | 0.348 (3) | 0.643 (3) | 0.398 (2) | 0.064 (7)* | |
H11 | 0.633 (3) | −0.032 (2) | 0.412 (2) | 0.062 (7)* | |
H2 | 0.054 (4) | 0.125 (3) | 0.471 (3) | 0.079 (8)* | |
H4 | 0.255 (3) | 0.073 (3) | 0.126 (2) | 0.061 (7)* | |
H12 | 0.726 (4) | −0.190 (3) | 0.276 (2) | 0.083 (9)* | |
H8B | 0.661 (4) | 0.538 (3) | 0.336 (2) | 0.066 (7)* | |
H3 | 0.142 (4) | −0.029 (3) | 0.330 (2) | 0.077 (8)* | |
H13 | 0.791 (4) | −0.105 (3) | 0.073 (3) | 0.085 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0644 (4) | 0.0341 (3) | 0.0371 (3) | 0.0038 (2) | −0.0152 (3) | −0.0079 (2) |
O3 | 0.0736 (11) | 0.0541 (10) | 0.0316 (9) | −0.0110 (8) | −0.0163 (8) | −0.0034 (7) |
O1 | 0.0626 (10) | 0.0633 (11) | 0.0480 (10) | 0.0156 (8) | −0.0079 (8) | −0.0166 (8) |
O4 | 0.0834 (12) | 0.0464 (10) | 0.0348 (9) | −0.0059 (8) | −0.0076 (8) | 0.0047 (7) |
N2 | 0.0464 (10) | 0.0352 (10) | 0.0335 (9) | −0.0071 (7) | −0.0108 (8) | −0.0029 (8) |
O2 | 0.1049 (14) | 0.0324 (9) | 0.0519 (10) | −0.0046 (8) | −0.0239 (10) | −0.0004 (8) |
N1 | 0.0659 (13) | 0.0389 (11) | 0.0279 (10) | −0.0082 (9) | −0.0109 (9) | −0.0044 (8) |
C6 | 0.0394 (11) | 0.0381 (13) | 0.0365 (11) | −0.0044 (9) | −0.0121 (9) | −0.0064 (9) |
C15 | 0.0397 (11) | 0.0407 (12) | 0.0339 (11) | −0.0002 (9) | −0.0087 (9) | −0.0044 (9) |
C10 | 0.0369 (11) | 0.0382 (13) | 0.0374 (11) | −0.0033 (9) | −0.0105 (9) | −0.0013 (9) |
C9 | 0.0396 (11) | 0.0433 (13) | 0.0354 (12) | −0.0083 (9) | −0.0136 (9) | −0.0006 (10) |
C16 | 0.0412 (12) | 0.0439 (13) | 0.0343 (12) | −0.0053 (9) | −0.0078 (9) | −0.0022 (10) |
C5 | 0.0545 (14) | 0.0516 (15) | 0.0383 (13) | −0.0089 (11) | −0.0128 (11) | −0.0110 (11) |
C1 | 0.0518 (13) | 0.0467 (14) | 0.0408 (13) | −0.0100 (10) | −0.0057 (10) | −0.0084 (11) |
C11 | 0.0514 (13) | 0.0435 (15) | 0.0455 (14) | −0.0026 (10) | −0.0126 (11) | 0.0029 (11) |
C8 | 0.0609 (15) | 0.0391 (13) | 0.0459 (14) | −0.0155 (11) | −0.0177 (12) | −0.0048 (11) |
C7 | 0.0667 (15) | 0.0397 (13) | 0.0364 (12) | −0.0048 (11) | −0.0177 (11) | −0.0126 (11) |
C14 | 0.0626 (15) | 0.0552 (17) | 0.0411 (14) | 0.0043 (12) | −0.0094 (12) | −0.0104 (12) |
C2 | 0.0604 (15) | 0.0521 (16) | 0.0532 (16) | −0.0190 (12) | −0.0096 (12) | 0.0052 (13) |
C4 | 0.0599 (15) | 0.0480 (16) | 0.0639 (17) | −0.0067 (11) | −0.0167 (13) | −0.0219 (14) |
C12 | 0.0644 (16) | 0.0378 (15) | 0.0661 (17) | 0.0030 (11) | −0.0167 (13) | −0.0064 (13) |
C13 | 0.0758 (18) | 0.0465 (16) | 0.0601 (17) | 0.0089 (13) | −0.0161 (14) | −0.0183 (14) |
C3 | 0.0597 (15) | 0.0405 (15) | 0.0708 (19) | −0.0116 (12) | −0.0158 (13) | −0.0051 (13) |
Geometric parameters (Å, º) top
S1—O1 | 1.4309 (17) | C1—C2 | 1.388 (3) |
S1—O2 | 1.4252 (17) | C1—H1A | 0.88 (2) |
S1—N1 | 1.6128 (19) | C11—C12 | 1.389 (4) |
S1—C7 | 1.772 (2) | C11—H11 | 0.93 (2) |
O3—C9 | 1.205 (2) | C8—C7 | 1.523 (3) |
O4—C16 | 1.211 (2) | C8—H8A | 0.98 (2) |
N2—C9 | 1.398 (3) | C8—H8B | 0.99 (3) |
N2—C16 | 1.389 (3) | C7—H7A | 0.96 (2) |
N2—C8 | 1.454 (3) | C7—H7B | 0.98 (3) |
N1—C6 | 1.416 (3) | C14—C13 | 1.385 (4) |
N1—H1 | 0.78 (2) | C14—H14 | 0.97 (3) |
C6—C5 | 1.385 (3) | C2—C3 | 1.364 (4) |
C6—C1 | 1.382 (3) | C2—H2 | 0.96 (3) |
C15—C10 | 1.390 (3) | C4—C3 | 1.364 (4) |
C15—C16 | 1.483 (3) | C4—H4 | 0.93 (2) |
C15—C14 | 1.372 (3) | C12—C13 | 1.378 (4) |
C10—C9 | 1.477 (3) | C12—H12 | 0.96 (3) |
C10—C11 | 1.372 (3) | C13—H13 | 0.98 (3) |
C5—C4 | 1.384 (3) | C3—H3 | 0.95 (3) |
C5—H5 | 0.94 (2) | | |
| | | |
O1—S1—N1 | 109.59 (11) | C10—C11—C12 | 117.2 (2) |
O1—S1—C7 | 105.69 (11) | C10—C11—H11 | 120.5 (15) |
O2—S1—O1 | 119.21 (11) | C12—C11—H11 | 122.2 (15) |
O2—S1—N1 | 104.80 (10) | N2—C8—C7 | 113.04 (19) |
O2—S1—C7 | 108.76 (12) | N2—C8—H8A | 105.8 (13) |
N1—S1—C7 | 108.48 (10) | N2—C8—H8B | 108.7 (14) |
C9—N2—C8 | 123.78 (17) | C7—C8—H8A | 114.5 (13) |
C16—N2—C9 | 111.55 (16) | C7—C8—H8B | 108.6 (15) |
C16—N2—C8 | 124.58 (17) | H8A—C8—H8B | 105.8 (19) |
S1—N1—H1 | 113.4 (18) | S1—C7—H7A | 108.9 (13) |
C6—N1—S1 | 126.66 (16) | S1—C7—H7B | 101.1 (14) |
C6—N1—H1 | 117.2 (18) | C8—C7—S1 | 115.95 (16) |
C5—C6—N1 | 117.89 (19) | C8—C7—H7A | 110.6 (13) |
C1—C6—N1 | 122.7 (2) | C8—C7—H7B | 109.4 (14) |
C1—C6—C5 | 119.4 (2) | H7A—C7—H7B | 110.4 (18) |
C10—C15—C16 | 107.72 (18) | C15—C14—C13 | 117.0 (2) |
C14—C15—C10 | 121.5 (2) | C15—C14—H14 | 122.4 (15) |
C14—C15—C16 | 130.8 (2) | C13—C14—H14 | 120.5 (15) |
C15—C10—C9 | 108.26 (18) | C1—C2—H2 | 113.0 (17) |
C11—C10—C15 | 121.5 (2) | C3—C2—C1 | 121.3 (3) |
C11—C10—C9 | 130.3 (2) | C3—C2—H2 | 125.5 (17) |
O3—C9—N2 | 124.30 (19) | C5—C4—H4 | 114.8 (15) |
O3—C9—C10 | 129.64 (19) | C3—C4—C5 | 121.1 (2) |
N2—C9—C10 | 106.06 (17) | C3—C4—H4 | 124.0 (15) |
O4—C16—N2 | 124.0 (2) | C11—C12—H12 | 119.7 (17) |
O4—C16—C15 | 129.6 (2) | C13—C12—C11 | 121.1 (3) |
N2—C16—C15 | 106.37 (17) | C13—C12—H12 | 119.3 (17) |
C6—C5—H5 | 122.7 (14) | C14—C13—H13 | 118.7 (17) |
C4—C5—C6 | 119.6 (2) | C12—C13—C14 | 121.7 (3) |
C4—C5—H5 | 117.6 (14) | C12—C13—H13 | 119.5 (17) |
C6—C1—C2 | 119.4 (2) | C2—C3—C4 | 119.1 (2) |
C6—C1—H1A | 120.9 (16) | C2—C3—H3 | 118.2 (17) |
C2—C1—H1A | 119.7 (16) | C4—C3—H3 | 122.7 (17) |
| | | |
S1—N1—C6—C5 | −166.01 (17) | C9—C10—C11—C12 | 179.6 (2) |
S1—N1—C6—C1 | 12.2 (3) | C16—N2—C9—O3 | 177.9 (2) |
O1—S1—N1—C6 | −58.6 (2) | C16—N2—C9—C10 | −2.0 (2) |
O1—S1—C7—C8 | 171.30 (17) | C16—N2—C8—C7 | 120.9 (2) |
N2—C8—C7—S1 | −84.7 (2) | C16—C15—C10—C9 | −0.6 (2) |
O2—S1—N1—C6 | 172.35 (18) | C16—C15—C10—C11 | 178.86 (18) |
O2—S1—C7—C8 | −59.6 (2) | C16—C15—C14—C13 | −179.2 (2) |
N1—S1—C7—C8 | 53.8 (2) | C5—C6—C1—C2 | 2.2 (3) |
N1—C6—C5—C4 | 176.71 (19) | C5—C4—C3—C2 | 1.3 (4) |
N1—C6—C1—C2 | −176.0 (2) | C1—C6—C5—C4 | −1.6 (3) |
C6—C5—C4—C3 | −0.2 (4) | C1—C2—C3—C4 | −0.6 (4) |
C6—C1—C2—C3 | −1.2 (4) | C11—C10—C9—O3 | 2.3 (4) |
C15—C10—C9—O3 | −178.3 (2) | C11—C10—C9—N2 | −177.8 (2) |
C15—C10—C9—N2 | 1.5 (2) | C11—C12—C13—C14 | −0.7 (4) |
C15—C10—C11—C12 | 0.3 (3) | C8—N2—C9—O3 | 1.2 (3) |
C15—C14—C13—C12 | 0.7 (4) | C8—N2—C9—C10 | −178.65 (18) |
C10—C15—C16—O4 | −180.0 (2) | C8—N2—C16—O4 | −2.3 (3) |
C10—C15—C16—N2 | −0.6 (2) | C8—N2—C16—C15 | 178.29 (18) |
C10—C15—C14—C13 | −0.1 (3) | C7—S1—N1—C6 | 56.3 (2) |
C10—C11—C12—C13 | 0.2 (4) | C14—C15—C10—C9 | −179.80 (19) |
C9—N2—C16—O4 | −178.97 (19) | C14—C15—C10—C11 | −0.4 (3) |
C9—N2—C16—C15 | 1.6 (2) | C14—C15—C16—O4 | −0.8 (4) |
C9—N2—C8—C7 | −62.9 (3) | C14—C15—C16—N2 | 178.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1 | 0.88 (2) | 2.56 (2) | 3.139 (3) | 124.1 (19) |
C7—H7A···O3 | 0.96 (2) | 2.54 (2) | 3.138 (3) | 120.5 (16) |
N1—H1···O4i | 0.78 (2) | 2.18 (3) | 2.934 (3) | 165 (2) |
C14—H14···O2i | 0.97 (3) | 2.43 (3) | 3.372 (3) | 166 (2) |
C7—H7B···O3ii | 0.98 (3) | 2.38 (3) | 3.237 (3) | 146.0 (18) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
N-(4-Nitrophenyl)-2-phthalimidoethanesulfonamide (II)
top
Crystal data top
C16H13N3O6S | Z = 2 |
Mr = 375.35 | F(000) = 388 |
Triclinic, P1 | Dx = 1.535 Mg m−3 |
a = 7.1547 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4322 (13) Å | Cell parameters from 2023 reflections |
c = 11.8228 (16) Å | θ = 3.8–28.1° |
α = 100.106 (11)° | µ = 0.24 mm−1 |
β = 104.043 (10)° | T = 293 K |
γ = 102.278 (9)° | Needle, colourless |
V = 812.13 (18) Å3 | 0.38 × 0.16 × 0.05 mm |
Data collection top
Rigaku OD Xcalibur Eos diffractometer | 2626 reflections with I > 2σ(I) |
Detector resolution: 16.1333 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 29.2°, θmin = 3.1° |
Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions
derived
by Clark & Reid (1995)] | h = −8→9 |
Tmin = 0.975, Tmax = 0.996 | k = −14→14 |
6276 measured reflections | l = −15→13 |
3661 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | All H-atom parameters refined |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.0498P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3661 reflections | Δρmax = 0.20 e Å−3 |
287 parameters | Δρmin = −0.38 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 | |
S1 | 1.02375 (7) | 0.68705 (5) | 0.22465 (5) | 0.03721 (16) | |
O3 | 0.3869 (2) | 0.48939 (14) | 0.08869 (13) | 0.0463 (4) | |
O1 | 0.9877 (2) | 0.77992 (13) | 0.15224 (14) | 0.0520 (4) | |
O2 | 1.2246 (2) | 0.68924 (14) | 0.28361 (14) | 0.0523 (4) | |
N2 | 0.5825 (2) | 0.53496 (14) | 0.28430 (14) | 0.0321 (4) | |
O4 | 0.7162 (2) | 0.51754 (15) | 0.47671 (13) | 0.0530 (4) | |
N1 | 0.9084 (2) | 0.53973 (16) | 0.13394 (16) | 0.0364 (4) | |
O6 | 0.8477 (3) | 0.02247 (17) | 0.33970 (18) | 0.0755 (6) | |
O5 | 0.6553 (3) | −0.06541 (15) | 0.15958 (18) | 0.0732 (6) | |
N3 | 0.7711 (3) | 0.03078 (18) | 0.2381 (2) | 0.0528 (5) | |
C6 | 0.8888 (3) | 0.41276 (17) | 0.16100 (17) | 0.0308 (4) | |
C9 | 0.4434 (3) | 0.45195 (19) | 0.17894 (18) | 0.0334 (4) | |
C5 | 0.9857 (3) | 0.3961 (2) | 0.27215 (19) | 0.0364 (5) | |
C16 | 0.6096 (3) | 0.46676 (19) | 0.37550 (18) | 0.0350 (4) | |
C3 | 0.8185 (3) | 0.16204 (18) | 0.20971 (19) | 0.0381 (5) | |
C15 | 0.4859 (3) | 0.32587 (18) | 0.32164 (19) | 0.0354 (4) | |
C4 | 0.9491 (3) | 0.2713 (2) | 0.2970 (2) | 0.0392 (5) | |
C8 | 0.6780 (3) | 0.67750 (19) | 0.3000 (2) | 0.0379 (5) | |
C7 | 0.9054 (3) | 0.7101 (2) | 0.33982 (19) | 0.0366 (5) | |
C1 | 0.7635 (3) | 0.3002 (2) | 0.07222 (19) | 0.0369 (5) | |
C10 | 0.3876 (3) | 0.31708 (18) | 0.20339 (18) | 0.0341 (4) | |
C2 | 0.7293 (3) | 0.1755 (2) | 0.0967 (2) | 0.0408 (5) | |
C11 | 0.2656 (3) | 0.1960 (2) | 0.1282 (2) | 0.0446 (5) | |
C12 | 0.2454 (4) | 0.0841 (2) | 0.1751 (3) | 0.0533 (6) | |
C14 | 0.4662 (3) | 0.2144 (2) | 0.3698 (3) | 0.0508 (6) | |
C13 | 0.3428 (4) | 0.0925 (2) | 0.2934 (3) | 0.0574 (7) | |
H1A | 0.705 (3) | 0.3160 (18) | −0.0030 (18) | 0.040 (6)* | |
H5 | 1.077 (3) | 0.470 (2) | 0.3308 (19) | 0.049 (6)* | |
H7A | 0.951 (3) | 0.6593 (17) | 0.3925 (16) | 0.027 (5)* | |
H1 | 0.829 (3) | 0.545 (2) | 0.0698 (19) | 0.042 (6)* | |
H8A | 0.627 (3) | 0.6983 (19) | 0.2222 (19) | 0.041 (6)* | |
H4 | 1.011 (3) | 0.2574 (19) | 0.3755 (19) | 0.041 (6)* | |
H7B | 0.957 (3) | 0.807 (2) | 0.3730 (18) | 0.044 (6)* | |
H2 | 0.645 (3) | 0.101 (2) | 0.037 (2) | 0.054 (6)* | |
H14 | 0.538 (3) | 0.222 (2) | 0.452 (2) | 0.054 (7)* | |
H11 | 0.204 (3) | 0.191 (2) | 0.049 (2) | 0.055 (7)* | |
H13 | 0.330 (3) | 0.014 (2) | 0.324 (2) | 0.057 (7)* | |
H8B | 0.635 (3) | 0.728 (2) | 0.362 (2) | 0.057 (7)* | |
H12 | 0.167 (4) | −0.007 (3) | 0.125 (2) | 0.083 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0314 (3) | 0.0326 (3) | 0.0407 (3) | −0.00170 (19) | 0.0070 (2) | 0.0086 (2) |
O3 | 0.0451 (9) | 0.0511 (8) | 0.0352 (9) | 0.0055 (7) | 0.0005 (7) | 0.0160 (7) |
O1 | 0.0634 (10) | 0.0365 (7) | 0.0523 (10) | 0.0009 (7) | 0.0139 (8) | 0.0205 (7) |
O2 | 0.0267 (8) | 0.0585 (9) | 0.0589 (10) | 0.0001 (6) | 0.0048 (7) | 0.0066 (8) |
N2 | 0.0284 (8) | 0.0306 (8) | 0.0319 (9) | 0.0033 (6) | 0.0035 (6) | 0.0067 (7) |
O4 | 0.0500 (9) | 0.0616 (10) | 0.0331 (9) | −0.0011 (7) | −0.0010 (7) | 0.0128 (8) |
N1 | 0.0381 (10) | 0.0333 (8) | 0.0304 (10) | 0.0052 (7) | 0.0003 (7) | 0.0077 (8) |
O6 | 0.1075 (16) | 0.0548 (10) | 0.0703 (13) | 0.0262 (10) | 0.0192 (11) | 0.0346 (10) |
O5 | 0.0769 (13) | 0.0327 (8) | 0.0942 (15) | 0.0045 (8) | 0.0059 (11) | 0.0138 (10) |
N3 | 0.0568 (13) | 0.0417 (11) | 0.0677 (15) | 0.0205 (9) | 0.0205 (11) | 0.0208 (11) |
C6 | 0.0269 (9) | 0.0316 (9) | 0.0322 (11) | 0.0072 (7) | 0.0071 (8) | 0.0065 (8) |
C9 | 0.0264 (9) | 0.0399 (10) | 0.0318 (11) | 0.0066 (8) | 0.0073 (8) | 0.0075 (9) |
C5 | 0.0338 (11) | 0.0342 (10) | 0.0351 (12) | 0.0094 (8) | 0.0018 (9) | 0.0035 (9) |
C16 | 0.0294 (10) | 0.0424 (10) | 0.0321 (11) | 0.0066 (8) | 0.0075 (8) | 0.0118 (9) |
C3 | 0.0364 (11) | 0.0321 (10) | 0.0486 (13) | 0.0128 (8) | 0.0137 (9) | 0.0107 (10) |
C15 | 0.0311 (10) | 0.0355 (10) | 0.0411 (12) | 0.0059 (8) | 0.0128 (9) | 0.0135 (9) |
C4 | 0.0404 (11) | 0.0426 (11) | 0.0353 (12) | 0.0178 (9) | 0.0062 (9) | 0.0099 (10) |
C8 | 0.0356 (11) | 0.0294 (10) | 0.0460 (14) | 0.0065 (8) | 0.0089 (10) | 0.0090 (10) |
C7 | 0.0347 (11) | 0.0284 (10) | 0.0377 (12) | 0.0023 (8) | 0.0030 (9) | 0.0030 (9) |
C1 | 0.0341 (11) | 0.0386 (10) | 0.0317 (12) | 0.0077 (8) | 0.0018 (8) | 0.0054 (9) |
C10 | 0.0264 (10) | 0.0356 (10) | 0.0386 (12) | 0.0041 (8) | 0.0115 (8) | 0.0064 (9) |
C2 | 0.0371 (11) | 0.0322 (10) | 0.0447 (13) | 0.0061 (9) | 0.0051 (9) | 0.0010 (10) |
C11 | 0.0364 (12) | 0.0409 (11) | 0.0469 (14) | −0.0012 (9) | 0.0115 (10) | 0.0013 (11) |
C12 | 0.0475 (14) | 0.0368 (12) | 0.0722 (19) | 0.0013 (10) | 0.0237 (13) | 0.0078 (13) |
C14 | 0.0456 (13) | 0.0547 (14) | 0.0592 (17) | 0.0128 (11) | 0.0180 (12) | 0.0288 (13) |
C13 | 0.0541 (15) | 0.0376 (12) | 0.092 (2) | 0.0088 (11) | 0.0330 (14) | 0.0315 (14) |
Geometric parameters (Å, º) top
S1—O1 | 1.4240 (15) | C3—C2 | 1.379 (3) |
S1—O2 | 1.4303 (14) | C15—C10 | 1.381 (3) |
S1—N1 | 1.6267 (17) | C15—C14 | 1.378 (3) |
S1—C7 | 1.778 (2) | C4—H4 | 0.98 (2) |
O3—C9 | 1.208 (2) | C8—C7 | 1.523 (3) |
N2—C9 | 1.395 (2) | C8—H8A | 0.98 (2) |
N2—C16 | 1.390 (2) | C8—H8B | 0.98 (2) |
N2—C8 | 1.457 (2) | C7—H7A | 0.931 (17) |
O4—C16 | 1.207 (2) | C7—H7B | 0.973 (19) |
N1—C6 | 1.403 (2) | C1—C2 | 1.366 (3) |
N1—H1 | 0.85 (2) | C1—H1A | 0.946 (19) |
O6—N3 | 1.220 (3) | C10—C11 | 1.382 (3) |
O5—N3 | 1.225 (2) | C2—H2 | 0.93 (2) |
N3—C3 | 1.457 (3) | C11—C12 | 1.373 (3) |
C6—C5 | 1.388 (3) | C11—H11 | 0.92 (2) |
C6—C1 | 1.396 (3) | C12—C13 | 1.381 (4) |
C9—C10 | 1.477 (3) | C12—H12 | 0.99 (3) |
C5—C4 | 1.370 (3) | C14—C13 | 1.395 (3) |
C5—H5 | 0.94 (2) | C14—H14 | 0.97 (2) |
C16—C15 | 1.481 (3) | C13—H13 | 0.95 (2) |
C3—C4 | 1.379 (3) | | |
| | | |
O1—S1—O2 | 119.81 (9) | C3—C4—H4 | 118.7 (12) |
O1—S1—N1 | 103.98 (9) | N2—C8—C7 | 112.68 (15) |
O1—S1—C7 | 108.73 (10) | N2—C8—H8A | 105.7 (12) |
O2—S1—N1 | 109.83 (9) | N2—C8—H8B | 107.0 (13) |
O2—S1—C7 | 105.94 (10) | C7—C8—H8A | 112.0 (12) |
N1—S1—C7 | 108.14 (9) | C7—C8—H8B | 108.6 (13) |
C9—N2—C8 | 124.61 (16) | H8A—C8—H8B | 110.8 (16) |
C16—N2—C9 | 111.40 (15) | S1—C7—H7A | 105.8 (11) |
C16—N2—C8 | 123.88 (17) | S1—C7—H7B | 100.8 (12) |
S1—N1—H1 | 112.3 (14) | C8—C7—S1 | 116.75 (15) |
C6—N1—S1 | 127.68 (15) | C8—C7—H7A | 111.9 (11) |
C6—N1—H1 | 118.0 (14) | C8—C7—H7B | 107.8 (11) |
O6—N3—O5 | 123.2 (2) | H7A—C7—H7B | 113.4 (16) |
O6—N3—C3 | 118.1 (2) | C6—C1—H1A | 116.5 (11) |
O5—N3—C3 | 118.7 (2) | C2—C1—C6 | 120.1 (2) |
C5—C6—N1 | 122.62 (17) | C2—C1—H1A | 123.4 (12) |
C5—C6—C1 | 119.53 (18) | C15—C10—C9 | 108.26 (16) |
C1—C6—N1 | 117.84 (18) | C15—C10—C11 | 121.4 (2) |
O3—C9—N2 | 124.12 (17) | C11—C10—C9 | 130.3 (2) |
O3—C9—C10 | 129.82 (18) | C3—C2—H2 | 121.1 (14) |
N2—C9—C10 | 106.05 (16) | C1—C2—C3 | 119.51 (19) |
C6—C5—H5 | 120.2 (12) | C1—C2—H2 | 119.4 (14) |
C4—C5—C6 | 120.19 (19) | C10—C11—H11 | 120.3 (14) |
C4—C5—H5 | 119.6 (12) | C12—C11—C10 | 117.6 (2) |
N2—C16—C15 | 106.20 (16) | C12—C11—H11 | 122.1 (14) |
O4—C16—N2 | 124.40 (18) | C11—C12—C13 | 121.2 (2) |
O4—C16—C15 | 129.40 (19) | C11—C12—H12 | 121.7 (15) |
C4—C3—N3 | 119.4 (2) | C13—C12—H12 | 117.0 (15) |
C2—C3—N3 | 119.41 (19) | C15—C14—C13 | 116.8 (2) |
C2—C3—C4 | 121.15 (19) | C15—C14—H14 | 120.6 (13) |
C10—C15—C16 | 107.95 (17) | C13—C14—H14 | 122.6 (13) |
C14—C15—C16 | 130.5 (2) | C12—C13—C14 | 121.5 (2) |
C14—C15—C10 | 121.5 (2) | C12—C13—H13 | 120.3 (14) |
C5—C4—C3 | 119.4 (2) | C14—C13—H13 | 118.2 (14) |
C5—C4—H4 | 121.9 (12) | | |
| | | |
S1—N1—C6—C5 | −6.1 (3) | C9—N2—C16—O4 | −177.00 (18) |
S1—N1—C6—C1 | 172.77 (15) | C9—N2—C16—C15 | 3.5 (2) |
O3—C9—C10—C15 | −177.44 (19) | C9—N2—C8—C7 | −124.43 (19) |
O3—C9—C10—C11 | 4.3 (3) | C9—C10—C11—C12 | 177.97 (18) |
O1—S1—N1—C6 | −176.98 (16) | C5—C6—C1—C2 | 3.2 (3) |
O1—S1—C7—C8 | 64.70 (17) | C16—N2—C9—O3 | 176.31 (17) |
O2—S1—N1—C6 | 53.64 (19) | C16—N2—C9—C10 | −3.9 (2) |
O2—S1—C7—C8 | −165.30 (14) | C16—N2—C8—C7 | 59.9 (2) |
N2—C9—C10—C15 | 2.83 (19) | C16—C15—C10—C9 | −0.8 (2) |
N2—C9—C10—C11 | −175.39 (19) | C16—C15—C10—C11 | 177.63 (17) |
N2—C16—C15—C10 | −1.6 (2) | C16—C15—C14—C13 | −177.10 (19) |
N2—C16—C15—C14 | 176.0 (2) | C15—C10—C11—C12 | 0.0 (3) |
N2—C8—C7—S1 | 85.6 (2) | C15—C14—C13—C12 | 0.1 (3) |
O4—C16—C15—C10 | 178.9 (2) | C4—C3—C2—C1 | −3.0 (3) |
O4—C16—C15—C14 | −3.5 (4) | C8—N2—C9—O3 | 0.1 (3) |
N1—S1—C7—C8 | −47.60 (17) | C8—N2—C9—C10 | 179.89 (16) |
N1—C6—C5—C4 | 174.84 (17) | C8—N2—C16—O4 | −0.8 (3) |
N1—C6—C1—C2 | −175.77 (17) | C8—N2—C16—C15 | 179.68 (16) |
O6—N3—C3—C4 | 0.9 (3) | C7—S1—N1—C6 | −61.54 (18) |
O6—N3—C3—C2 | −178.0 (2) | C1—C6—C5—C4 | −4.0 (3) |
O5—N3—C3—C4 | −179.81 (19) | C10—C15—C14—C13 | 0.1 (3) |
O5—N3—C3—C2 | 1.3 (3) | C10—C11—C12—C13 | 0.3 (3) |
N3—C3—C4—C5 | −176.70 (17) | C2—C3—C4—C5 | 2.1 (3) |
N3—C3—C2—C1 | 175.83 (17) | C11—C12—C13—C14 | −0.3 (4) |
C6—C5—C4—C3 | 1.4 (3) | C14—C15—C10—C9 | −178.57 (17) |
C6—C1—C2—C3 | 0.3 (3) | C14—C15—C10—C11 | −0.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2 | 0.94 (2) | 2.52 (2) | 3.132 (3) | 123.0 (15) |
C7—H7A···O4 | 0.931 (17) | 2.505 (18) | 3.088 (3) | 120.9 (13) |
C5—H5···O4i | 0.94 (2) | 2.36 (2) | 3.057 (3) | 130.6 (15) |
N1—H1···O3ii | 0.85 (2) | 2.04 (2) | 2.869 (2) | 166 (2) |
C1—H1A···O3ii | 0.946 (19) | 2.558 (19) | 3.328 (3) | 138.7 (14) |
C11—H11···O1ii | 0.92 (2) | 2.55 (2) | 3.451 (3) | 168.6 (18) |
C7—H7B···O6iii | 0.973 (19) | 2.594 (19) | 3.371 (3) | 136.9 (15) |
C12—H12···O1iv | 0.99 (3) | 2.44 (3) | 3.241 (3) | 138 (2) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y+1, z; (iv) x−1, y−1, z. |
N-(4-Methoxyphenyl)-2-phthalimidoethanesulfonamide (III)
top
Crystal data top
C17H16N2O5S | F(000) = 752 |
Mr = 360.38 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9408 (9) Å | Cell parameters from 1361 reflections |
b = 7.2555 (7) Å | θ = 3.8–27.6° |
c = 21.1923 (18) Å | µ = 0.23 mm−1 |
β = 99.838 (8)° | T = 293 K |
V = 1657.5 (3) Å3 | Needle, colourless |
Z = 4 | 0.53 × 0.42 × 0.06 mm |
Data collection top
Rigaku OD Xcalibur Eos diffractometer | 2153 reflections with I > 2σ(I) |
Detector resolution: 16.1333 pixels mm-1 | Rint = 0.019 |
ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions
derived
by Clark & Reid (1995)] | h = −9→13 |
Tmin = 0.979, Tmax = 0.997 | k = −4→8 |
5141 measured reflections | l = −18→25 |
2907 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0416P)2 + 0.2139P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2907 reflections | Δρmax = 0.13 e Å−3 |
290 parameters | Δρmin = −0.31 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 | |
S1 | 0.43556 (4) | 0.54727 (8) | 0.59432 (2) | 0.04821 (18) | |
O5 | 1.00320 (13) | 0.5216 (2) | 0.76716 (7) | 0.0621 (5) | |
O2 | 0.35392 (13) | 0.4831 (2) | 0.53852 (7) | 0.0641 (5) | |
O1 | 0.40466 (13) | 0.5129 (2) | 0.65539 (7) | 0.0654 (5) | |
O4 | 0.10455 (15) | 0.7307 (3) | 0.58806 (8) | 0.0753 (5) | |
N2 | 0.24268 (15) | 0.8706 (3) | 0.53338 (8) | 0.0507 (5) | |
O3 | 0.33224 (14) | 1.0018 (3) | 0.45398 (9) | 0.0794 (6) | |
N1 | 0.56844 (17) | 0.4530 (3) | 0.59052 (10) | 0.0609 (6) | |
C10 | 0.12470 (18) | 0.8725 (3) | 0.43301 (10) | 0.0466 (5) | |
C15 | 0.05539 (17) | 0.7886 (3) | 0.47369 (10) | 0.0474 (5) | |
C16 | 0.13006 (19) | 0.7881 (3) | 0.53876 (11) | 0.0519 (5) | |
C3 | 0.89736 (17) | 0.5165 (3) | 0.72260 (9) | 0.0452 (5) | |
C4 | 0.88529 (19) | 0.5988 (3) | 0.66360 (10) | 0.0473 (5) | |
C6 | 0.67772 (18) | 0.4833 (3) | 0.63749 (10) | 0.0467 (5) | |
C9 | 0.24536 (19) | 0.9256 (3) | 0.47103 (11) | 0.0522 (5) | |
C5 | 0.77489 (19) | 0.5823 (3) | 0.62138 (10) | 0.0498 (6) | |
C1 | 0.6900 (2) | 0.4030 (4) | 0.69689 (11) | 0.0567 (6) | |
C7 | 0.45669 (19) | 0.7861 (3) | 0.58534 (12) | 0.0534 (6) | |
C2 | 0.7984 (2) | 0.4204 (4) | 0.73947 (11) | 0.0578 (6) | |
C14 | −0.0624 (2) | 0.7243 (3) | 0.45135 (14) | 0.0603 (6) | |
C11 | 0.0783 (2) | 0.8943 (4) | 0.36898 (12) | 0.0592 (6) | |
C13 | −0.1085 (2) | 0.7452 (4) | 0.38774 (14) | 0.0666 (7) | |
C8 | 0.3417 (2) | 0.9009 (4) | 0.58732 (13) | 0.0620 (6) | |
C12 | −0.0406 (2) | 0.8295 (4) | 0.34698 (14) | 0.0664 (7) | |
C17 | 1.1070 (3) | 0.6182 (6) | 0.75024 (15) | 0.0731 (8) | |
H4 | 0.9516 (19) | 0.666 (3) | 0.6511 (9) | 0.058 (6)* | |
H5 | 0.7677 (17) | 0.639 (3) | 0.5809 (10) | 0.057 (6)* | |
H7A | 0.4918 (18) | 0.800 (3) | 0.5465 (10) | 0.060 (6)* | |
H1A | 0.626 (2) | 0.337 (3) | 0.7088 (10) | 0.062 (7)* | |
H7B | 0.519 (2) | 0.820 (3) | 0.6178 (11) | 0.066 (7)* | |
H14 | −0.1082 (19) | 0.666 (3) | 0.4782 (10) | 0.060 (7)* | |
H11 | 0.126 (2) | 0.947 (3) | 0.3418 (10) | 0.061 (7)* | |
H13 | −0.189 (2) | 0.703 (3) | 0.3715 (10) | 0.071 (7)* | |
H17A | 1.133 (2) | 0.569 (4) | 0.7127 (12) | 0.076 (8)* | |
H2 | 0.8088 (19) | 0.365 (3) | 0.7806 (11) | 0.068 (7)* | |
H8A | 0.305 (2) | 0.868 (3) | 0.6255 (11) | 0.072 (7)* | |
H17B | 1.169 (3) | 0.604 (4) | 0.7857 (13) | 0.089 (9)* | |
H12 | −0.076 (2) | 0.845 (4) | 0.2987 (12) | 0.080 (7)* | |
H1 | 0.583 (3) | 0.463 (4) | 0.5552 (13) | 0.085 (10)* | |
H8B | 0.369 (3) | 1.034 (4) | 0.5859 (13) | 0.102 (10)* | |
H17C | 1.086 (3) | 0.755 (5) | 0.7427 (15) | 0.126 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0349 (3) | 0.0580 (4) | 0.0499 (3) | −0.0043 (2) | 0.0022 (2) | 0.0011 (3) |
O5 | 0.0430 (8) | 0.0877 (13) | 0.0516 (8) | −0.0047 (8) | −0.0030 (7) | 0.0096 (8) |
O2 | 0.0424 (8) | 0.0764 (12) | 0.0678 (10) | −0.0062 (8) | −0.0071 (7) | −0.0159 (9) |
O1 | 0.0547 (9) | 0.0825 (13) | 0.0608 (9) | −0.0013 (8) | 0.0154 (7) | 0.0228 (9) |
O4 | 0.0704 (11) | 0.0883 (14) | 0.0737 (11) | −0.0066 (10) | 0.0314 (9) | 0.0097 (10) |
N2 | 0.0393 (9) | 0.0503 (12) | 0.0621 (11) | −0.0022 (8) | 0.0072 (8) | 0.0057 (9) |
O3 | 0.0487 (10) | 0.0961 (15) | 0.0922 (12) | −0.0251 (9) | 0.0084 (9) | 0.0315 (11) |
N1 | 0.0444 (11) | 0.0797 (16) | 0.0559 (12) | 0.0074 (10) | 0.0008 (9) | −0.0103 (12) |
C10 | 0.0370 (11) | 0.0376 (12) | 0.0659 (13) | 0.0030 (9) | 0.0106 (10) | 0.0043 (11) |
C15 | 0.0350 (11) | 0.0392 (12) | 0.0702 (14) | 0.0026 (9) | 0.0151 (10) | −0.0012 (11) |
C16 | 0.0448 (12) | 0.0450 (13) | 0.0698 (14) | 0.0025 (10) | 0.0207 (11) | 0.0027 (12) |
C3 | 0.0372 (11) | 0.0519 (14) | 0.0454 (11) | 0.0048 (9) | 0.0034 (9) | 0.0010 (10) |
C4 | 0.0402 (11) | 0.0519 (14) | 0.0515 (12) | 0.0003 (10) | 0.0126 (10) | 0.0072 (11) |
C6 | 0.0368 (11) | 0.0521 (14) | 0.0491 (11) | 0.0064 (10) | 0.0014 (9) | −0.0013 (10) |
C9 | 0.0387 (12) | 0.0455 (13) | 0.0730 (14) | −0.0004 (10) | 0.0112 (10) | 0.0103 (12) |
C5 | 0.0444 (12) | 0.0627 (15) | 0.0426 (11) | 0.0045 (11) | 0.0086 (9) | 0.0077 (11) |
C1 | 0.0411 (12) | 0.0641 (16) | 0.0653 (14) | −0.0036 (12) | 0.0098 (11) | 0.0175 (13) |
C7 | 0.0392 (12) | 0.0632 (16) | 0.0545 (13) | −0.0133 (11) | −0.0012 (10) | 0.0044 (12) |
C2 | 0.0485 (13) | 0.0719 (17) | 0.0523 (12) | −0.0013 (12) | 0.0064 (10) | 0.0231 (13) |
C14 | 0.0416 (13) | 0.0500 (15) | 0.0924 (18) | −0.0027 (11) | 0.0199 (13) | −0.0024 (14) |
C11 | 0.0539 (14) | 0.0543 (15) | 0.0700 (15) | 0.0040 (12) | 0.0121 (12) | 0.0076 (13) |
C13 | 0.0383 (13) | 0.0583 (16) | 0.099 (2) | 0.0011 (12) | −0.0007 (13) | −0.0128 (15) |
C8 | 0.0566 (15) | 0.0583 (17) | 0.0673 (16) | −0.0047 (13) | 0.0004 (12) | −0.0036 (14) |
C12 | 0.0556 (15) | 0.0602 (16) | 0.0771 (17) | 0.0114 (13) | −0.0063 (13) | −0.0065 (14) |
C17 | 0.0462 (15) | 0.105 (3) | 0.0650 (17) | −0.0168 (16) | 0.0008 (13) | −0.0030 (19) |
Geometric parameters (Å, º) top
S1—O2 | 1.4324 (15) | C6—C5 | 1.374 (3) |
S1—O1 | 1.4145 (14) | C6—C1 | 1.372 (3) |
S1—N1 | 1.621 (2) | C5—H5 | 0.94 (2) |
S1—C7 | 1.763 (3) | C1—C2 | 1.368 (3) |
O5—C3 | 1.364 (2) | C1—H1A | 0.92 (2) |
O5—C17 | 1.431 (3) | C7—C8 | 1.515 (3) |
O4—C16 | 1.201 (2) | C7—H7A | 0.97 (2) |
N2—C16 | 1.392 (3) | C7—H7B | 0.92 (2) |
N2—C9 | 1.385 (3) | C2—H2 | 0.95 (2) |
N2—C8 | 1.451 (3) | C14—C13 | 1.365 (3) |
O3—C9 | 1.207 (2) | C14—H14 | 0.92 (2) |
N1—C6 | 1.436 (3) | C11—C12 | 1.386 (3) |
N1—H1 | 0.80 (3) | C11—H11 | 0.93 (2) |
C10—C15 | 1.383 (3) | C13—C12 | 1.375 (4) |
C10—C9 | 1.475 (3) | C13—H13 | 0.94 (2) |
C10—C11 | 1.374 (3) | C8—H8A | 0.99 (2) |
C15—C16 | 1.478 (3) | C8—H8B | 1.01 (3) |
C15—C14 | 1.376 (3) | C12—H12 | 1.04 (2) |
C3—C4 | 1.371 (3) | C17—H17A | 0.96 (3) |
C3—C2 | 1.385 (3) | C17—H17B | 0.93 (3) |
C4—C5 | 1.380 (3) | C17—H17C | 1.03 (4) |
C4—H4 | 0.95 (2) | | |
| | | |
O2—S1—N1 | 105.06 (10) | C6—C1—H1A | 120.9 (14) |
O2—S1—C7 | 107.77 (10) | C2—C1—C6 | 120.2 (2) |
O1—S1—O2 | 119.03 (10) | C2—C1—H1A | 118.9 (14) |
O1—S1—N1 | 109.13 (11) | S1—C7—H7A | 105.9 (14) |
O1—S1—C7 | 109.15 (11) | S1—C7—H7B | 106.0 (15) |
N1—S1—C7 | 105.92 (11) | C8—C7—S1 | 114.37 (17) |
C3—O5—C17 | 117.11 (18) | C8—C7—H7A | 114.6 (13) |
C16—N2—C8 | 123.57 (19) | C8—C7—H7B | 110.4 (15) |
C9—N2—C16 | 111.43 (17) | H7A—C7—H7B | 104.9 (17) |
C9—N2—C8 | 124.96 (18) | C3—C2—H2 | 118.3 (13) |
S1—N1—H1 | 110 (2) | C1—C2—C3 | 120.3 (2) |
C6—N1—S1 | 123.26 (16) | C1—C2—H2 | 121.4 (13) |
C6—N1—H1 | 111 (2) | C15—C14—H14 | 121.2 (14) |
C15—C10—C9 | 108.03 (19) | C13—C14—C15 | 118.0 (2) |
C11—C10—C15 | 121.1 (2) | C13—C14—H14 | 120.8 (13) |
C11—C10—C9 | 130.9 (2) | C10—C11—C12 | 117.4 (2) |
C10—C15—C16 | 107.94 (18) | C10—C11—H11 | 120.5 (14) |
C14—C15—C10 | 121.1 (2) | C12—C11—H11 | 122.0 (14) |
C14—C15—C16 | 131.0 (2) | C14—C13—C12 | 121.4 (2) |
O4—C16—N2 | 124.1 (2) | C14—C13—H13 | 119.4 (14) |
O4—C16—C15 | 129.7 (2) | C12—C13—H13 | 119.1 (14) |
N2—C16—C15 | 106.18 (18) | N2—C8—C7 | 114.0 (2) |
O5—C3—C4 | 123.89 (18) | N2—C8—H8A | 104.9 (13) |
O5—C3—C2 | 116.32 (18) | N2—C8—H8B | 107.7 (17) |
C4—C3—C2 | 119.78 (19) | C7—C8—H8A | 110.1 (14) |
C3—C4—C5 | 119.4 (2) | C7—C8—H8B | 106.0 (17) |
C3—C4—H4 | 121.3 (13) | H8A—C8—H8B | 114 (2) |
C5—C4—H4 | 119.3 (12) | C11—C12—H12 | 117.8 (13) |
C5—C6—N1 | 119.72 (19) | C13—C12—C11 | 121.1 (3) |
C1—C6—N1 | 120.7 (2) | C13—C12—H12 | 121.2 (13) |
C1—C6—C5 | 119.43 (19) | O5—C17—H17A | 112.7 (16) |
N2—C9—C10 | 106.42 (17) | O5—C17—H17B | 103.9 (17) |
O3—C9—N2 | 124.3 (2) | O5—C17—H17C | 110.5 (18) |
O3—C9—C10 | 129.3 (2) | H17A—C17—H17B | 111 (2) |
C4—C5—H5 | 118.7 (12) | H17A—C17—H17C | 108 (2) |
C6—C5—C4 | 120.9 (2) | H17B—C17—H17C | 110 (3) |
C6—C5—H5 | 120.4 (12) | | |
| | | |
S1—N1—C6—C5 | −110.8 (2) | C4—C3—C2—C1 | 1.8 (4) |
S1—N1—C6—C1 | 74.0 (3) | C6—C1—C2—C3 | −1.1 (4) |
S1—C7—C8—N2 | −66.9 (3) | C9—N2—C16—O4 | −179.1 (2) |
O5—C3—C4—C5 | 178.6 (2) | C9—N2—C16—C15 | 0.9 (2) |
O5—C3—C2—C1 | −177.8 (2) | C9—N2—C8—C7 | −70.2 (3) |
O2—S1—N1—C6 | 179.29 (19) | C9—C10—C15—C16 | 0.6 (2) |
O2—S1—C7—C8 | 67.78 (19) | C9—C10—C15—C14 | 179.92 (19) |
O1—S1—N1—C6 | −52.0 (2) | C9—C10—C11—C12 | −179.8 (2) |
O1—S1—C7—C8 | −62.81 (19) | C5—C6—C1—C2 | −0.5 (4) |
N1—S1—C7—C8 | 179.82 (17) | C1—C6—C5—C4 | 1.4 (3) |
N1—C6—C5—C4 | −173.9 (2) | C7—S1—N1—C6 | 65.4 (2) |
N1—C6—C1—C2 | 174.7 (2) | C2—C3—C4—C5 | −1.0 (3) |
C10—C15—C16—O4 | 179.2 (2) | C14—C15—C16—O4 | −0.1 (4) |
C10—C15—C16—N2 | −0.9 (2) | C14—C15—C16—N2 | 179.8 (2) |
C10—C15—C14—C13 | 0.3 (3) | C14—C13—C12—C11 | 0.9 (4) |
C10—C11—C12—C13 | −0.6 (4) | C11—C10—C15—C16 | −179.4 (2) |
C15—C10—C9—N2 | 0.0 (2) | C11—C10—C15—C14 | −0.1 (3) |
C15—C10—C9—O3 | 180.0 (2) | C11—C10—C9—N2 | 180.0 (2) |
C15—C10—C11—C12 | 0.2 (3) | C11—C10—C9—O3 | 0.0 (4) |
C15—C14—C13—C12 | −0.7 (4) | C8—N2—C16—O4 | −1.6 (3) |
C16—N2—C9—O3 | 179.4 (2) | C8—N2—C16—C15 | 178.47 (19) |
C16—N2—C9—C10 | −0.6 (2) | C8—N2—C9—O3 | 1.9 (4) |
C16—N2—C8—C7 | 112.6 (2) | C8—N2—C9—C10 | −178.10 (19) |
C16—C15—C14—C13 | 179.5 (2) | C17—O5—C3—C4 | −0.4 (3) |
C3—C4—C5—C6 | −0.6 (3) | C17—O5—C3—C2 | 179.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O4i | 0.95 (2) | 2.36 (2) | 3.247 (3) | 155.7 (17) |
C7—H7A···O3ii | 0.97 (2) | 2.40 (2) | 3.009 (3) | 120.0 (16) |
N1—H1···O2iii | 0.80 (3) | 2.24 (3) | 3.035 (3) | 172 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1. |
Crystal data top
C18H18N2O4S·H2O | F(000) = 792 |
Mr = 376.42 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.356 (3) Å | Cell parameters from 1635 reflections |
b = 7.4014 (5) Å | θ = 3.8–25.8° |
c = 25.061 (5) Å | µ = 0.21 mm−1 |
β = 141.36 (4)° | T = 293 K |
V = 1778.6 (11) Å3 | Prism, colourless |
Z = 4 | 0.23 × 0.14 × 0.10 mm |
Data collection top
Rigaku OD Xcalibur Eos diffractometer | 2053 reflections with I > 2σ(I) |
Detector resolution: 16.1333 pixels mm-1 | Rint = 0.043 |
ω scans | θmax = 29.1°, θmin = 3.1° |
Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions
derived
by Clark & Reid (1995)] | h = −20→19 |
Tmin = 0.992, Tmax = 0.996 | k = −10→9 |
8757 measured reflections | l = −34→32 |
4113 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
4113 reflections | Δρmax = 0.21 e Å−3 |
304 parameters | Δρmin = −0.34 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. |
Refinement. H atoms of the methyl group were treated as riding atoms,
with C H distances of 0.96 A with Uiso(H) = 1.5Ueq(C). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.28266 (7) | 0.75110 (11) | 0.52435 (4) | 0.0430 (2) | |
O1 | 0.32461 (19) | 0.9159 (3) | 0.51933 (12) | 0.0576 (6) | |
O2 | 0.16137 (17) | 0.6587 (3) | 0.44811 (10) | 0.0600 (6) | |
O3 | 0.4185 (2) | 0.6094 (3) | 0.76957 (12) | 0.0615 (6) | |
N1 | 0.4091 (2) | 0.6104 (4) | 0.58053 (14) | 0.0410 (6) | |
N2 | 0.1944 (2) | 0.6865 (3) | 0.63929 (13) | 0.0430 (6) | |
O4 | −0.0320 (2) | 0.7845 (3) | 0.53337 (12) | 0.0702 (7) | |
O5 | 0.3241 (4) | 0.2695 (4) | 0.5741 (2) | 0.0750 (8) | |
C6 | 0.5516 (2) | 0.6568 (4) | 0.66143 (15) | 0.0370 (6) | |
C7 | 0.2565 (3) | 0.8028 (4) | 0.5804 (2) | 0.0414 (7) | |
C15 | 0.1114 (3) | 0.7677 (4) | 0.68157 (17) | 0.0476 (7) | |
C5 | 0.5989 (3) | 0.6385 (4) | 0.73563 (18) | 0.0442 (7) | |
C8 | 0.2044 (3) | 0.6432 (5) | 0.5874 (2) | 0.0470 (8) | |
C10 | 0.2489 (3) | 0.7153 (4) | 0.75395 (17) | 0.0471 (8) | |
C9 | 0.3040 (3) | 0.6621 (4) | 0.72741 (17) | 0.0457 (7) | |
C1 | 0.6392 (3) | 0.7135 (4) | 0.66228 (16) | 0.0430 (7) | |
C16 | 0.0761 (3) | 0.7507 (4) | 0.60765 (18) | 0.0475 (7) | |
C4 | 0.7352 (3) | 0.6779 (4) | 0.8132 (2) | 0.0524 (8) | |
C2 | 0.7764 (3) | 0.7518 (5) | 0.74201 (19) | 0.0546 (8) | |
C11 | 0.3108 (4) | 0.7133 (5) | 0.8328 (2) | 0.0635 (10) | |
C17 | 0.5864 (3) | 0.7287 (6) | 0.5806 (2) | 0.0611 (10) | |
C14 | 0.0321 (4) | 0.8194 (5) | 0.6866 (2) | 0.0703 (11) | |
C3 | 0.8231 (3) | 0.7349 (5) | 0.8159 (2) | 0.0573 (8) | |
C13 | 0.0938 (4) | 0.8159 (6) | 0.7657 (2) | 0.0786 (12) | |
C18 | 0.6957 (3) | 0.7507 (5) | 0.5899 (2) | 0.0782 (10) | |
H18A | 0.7424 | 0.8644 | 0.6168 | 0.117* | |
H18B | 0.6517 | 0.7474 | 0.5344 | 0.117* | |
H18C | 0.7623 | 0.6543 | 0.6243 | 0.117* | |
C12 | 0.2296 (4) | 0.7648 (5) | 0.8371 (2) | 0.0762 (12) | |
H4 | 0.767 (2) | 0.664 (3) | 0.8631 (16) | 0.053 (8)* | |
H7A | 0.344 (2) | 0.853 (3) | 0.6352 (15) | 0.038 (7)* | |
H7B | 0.189 (2) | 0.902 (3) | 0.5479 (14) | 0.047 (8)* | |
H8A | 0.271 (2) | 0.544 (4) | 0.6171 (15) | 0.054 (9)* | |
H8B | 0.113 (2) | 0.601 (3) | 0.5336 (16) | 0.051 (8)* | |
H2 | 0.837 (3) | 0.797 (4) | 0.7435 (17) | 0.069 (9)* | |
H12 | 0.270 (3) | 0.764 (4) | 0.890 (2) | 0.081 (10)* | |
H3 | 0.915 (3) | 0.762 (4) | 0.8677 (18) | 0.072 (10)* | |
H17A | 0.538 (3) | 0.619 (4) | 0.5512 (17) | 0.065 (11)* | |
H14 | −0.062 (3) | 0.856 (4) | 0.6360 (18) | 0.071 (10)* | |
H5 | 0.533 (3) | 0.599 (4) | 0.7316 (17) | 0.078 (10)* | |
H13 | 0.039 (3) | 0.856 (4) | 0.7718 (18) | 0.085 (10)* | |
H11 | 0.406 (3) | 0.674 (4) | 0.883 (2) | 0.080 (11)* | |
H1 | 0.389 (2) | 0.513 (4) | 0.5800 (15) | 0.038 (9)* | |
H5A | 0.396 (6) | 0.183 (7) | 0.609 (4) | 0.20 (3)* | |
H17B | 0.518 (3) | 0.831 (4) | 0.5469 (19) | 0.081 (11)* | |
H5B | 0.256 (4) | 0.244 (6) | 0.535 (3) | 0.11 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0429 (4) | 0.0571 (5) | 0.0383 (4) | 0.0043 (4) | 0.0341 (3) | 0.0033 (4) |
O1 | 0.0798 (13) | 0.0515 (14) | 0.0765 (13) | 0.0103 (11) | 0.0698 (12) | 0.0172 (11) |
O2 | 0.0390 (11) | 0.0961 (18) | 0.0352 (10) | −0.0018 (11) | 0.0266 (10) | −0.0101 (11) |
O3 | 0.0494 (12) | 0.0800 (17) | 0.0523 (12) | 0.0042 (11) | 0.0391 (11) | 0.0036 (11) |
N1 | 0.0376 (13) | 0.0432 (18) | 0.0427 (14) | −0.0039 (12) | 0.0315 (12) | −0.0025 (12) |
N2 | 0.0454 (13) | 0.0566 (17) | 0.0390 (13) | −0.0031 (11) | 0.0360 (12) | −0.0024 (11) |
O4 | 0.0438 (11) | 0.120 (2) | 0.0429 (12) | 0.0048 (12) | 0.0330 (11) | 0.0019 (12) |
O5 | 0.0721 (19) | 0.0574 (18) | 0.091 (2) | −0.0055 (16) | 0.0628 (18) | −0.0010 (16) |
C6 | 0.0353 (14) | 0.0396 (17) | 0.0361 (15) | −0.0004 (12) | 0.0278 (13) | −0.0019 (13) |
C7 | 0.0448 (17) | 0.048 (2) | 0.0418 (17) | 0.0008 (15) | 0.0363 (16) | 0.0000 (15) |
C15 | 0.0474 (16) | 0.063 (2) | 0.0460 (16) | −0.0131 (16) | 0.0399 (15) | −0.0096 (16) |
C5 | 0.0451 (17) | 0.048 (2) | 0.0450 (17) | 0.0046 (15) | 0.0367 (16) | 0.0051 (14) |
C8 | 0.0481 (18) | 0.061 (2) | 0.0460 (18) | −0.0081 (18) | 0.0403 (17) | −0.0079 (17) |
C10 | 0.0553 (18) | 0.053 (2) | 0.0464 (16) | −0.0123 (14) | 0.0431 (16) | −0.0066 (14) |
C9 | 0.0460 (17) | 0.051 (2) | 0.0429 (17) | −0.0068 (15) | 0.0354 (15) | −0.0021 (15) |
C1 | 0.0402 (15) | 0.050 (2) | 0.0472 (16) | −0.0015 (13) | 0.0362 (14) | −0.0019 (14) |
C16 | 0.0422 (15) | 0.064 (2) | 0.0421 (16) | −0.0071 (16) | 0.0344 (15) | −0.0046 (17) |
C4 | 0.0534 (19) | 0.062 (2) | 0.0434 (18) | 0.0066 (16) | 0.0381 (17) | 0.0056 (16) |
C2 | 0.0455 (17) | 0.068 (2) | 0.0569 (19) | −0.0064 (17) | 0.0416 (16) | −0.0034 (18) |
C11 | 0.070 (2) | 0.079 (3) | 0.0464 (19) | −0.013 (2) | 0.0467 (19) | −0.0068 (18) |
C17 | 0.057 (2) | 0.093 (3) | 0.0513 (19) | −0.007 (2) | 0.0469 (18) | −0.004 (2) |
C14 | 0.060 (2) | 0.107 (3) | 0.067 (2) | −0.014 (2) | 0.055 (2) | −0.015 (2) |
C3 | 0.0384 (17) | 0.067 (2) | 0.0419 (18) | −0.0010 (17) | 0.0251 (16) | −0.0038 (17) |
C13 | 0.080 (3) | 0.120 (4) | 0.076 (2) | −0.023 (2) | 0.071 (2) | −0.026 (2) |
C18 | 0.086 (2) | 0.103 (3) | 0.092 (2) | 0.003 (2) | 0.081 (2) | 0.009 (2) |
C12 | 0.091 (3) | 0.106 (3) | 0.060 (2) | −0.026 (2) | 0.066 (2) | −0.019 (2) |
Geometric parameters (Å, º) top
S1—O1 | 1.4302 (19) | C8—H8B | 0.97 (2) |
S1—O2 | 1.424 (2) | C10—C9 | 1.482 (4) |
S1—N1 | 1.602 (3) | C10—C11 | 1.369 (4) |
S1—C7 | 1.777 (3) | C1—C2 | 1.391 (4) |
O3—C9 | 1.207 (3) | C1—C17 | 1.505 (4) |
N1—C6 | 1.445 (3) | C4—C3 | 1.364 (4) |
N1—H1 | 0.78 (3) | C4—H4 | 0.93 (3) |
N2—C8 | 1.459 (3) | C2—C3 | 1.372 (4) |
N2—C9 | 1.391 (3) | C2—H2 | 0.97 (3) |
N2—C16 | 1.380 (3) | C11—C12 | 1.387 (5) |
O4—C16 | 1.207 (3) | C11—H11 | 0.96 (3) |
O5—H5A | 0.94 (6) | C17—C18 | 1.513 (4) |
O5—H5B | 0.70 (4) | C17—H17A | 0.95 (3) |
C6—C5 | 1.376 (3) | C17—H17B | 1.00 (3) |
C6—C1 | 1.394 (3) | C14—C13 | 1.375 (4) |
C7—C8 | 1.512 (4) | C14—H14 | 0.95 (3) |
C7—H7A | 0.97 (2) | C3—H3 | 0.93 (3) |
C7—H7B | 0.98 (2) | C13—C12 | 1.365 (5) |
C15—C10 | 1.383 (4) | C13—H13 | 1.01 (3) |
C15—C16 | 1.474 (3) | C18—H18A | 0.9600 |
C15—C14 | 1.375 (4) | C18—H18B | 0.9600 |
C5—C4 | 1.375 (4) | C18—H18C | 0.9600 |
C5—H5 | 0.98 (3) | C12—H12 | 0.94 (3) |
C8—H8A | 0.97 (3) | | |
| | | |
O1—S1—N1 | 108.18 (13) | C6—C1—C17 | 120.9 (2) |
O1—S1—C7 | 106.33 (13) | C2—C1—C6 | 116.3 (2) |
O2—S1—O1 | 119.91 (12) | C2—C1—C17 | 122.8 (2) |
O2—S1—N1 | 106.50 (14) | N2—C16—C15 | 106.3 (2) |
O2—S1—C7 | 107.30 (13) | O4—C16—N2 | 124.4 (2) |
N1—S1—C7 | 108.18 (14) | O4—C16—C15 | 129.3 (3) |
S1—N1—H1 | 113.0 (19) | C5—C4—H4 | 119.9 (15) |
C6—N1—S1 | 123.1 (2) | C3—C4—C5 | 119.4 (3) |
C6—N1—H1 | 113.0 (19) | C3—C4—H4 | 120.7 (15) |
C9—N2—C8 | 123.2 (2) | C1—C2—H2 | 117.4 (16) |
C16—N2—C8 | 124.8 (2) | C3—C2—C1 | 121.9 (3) |
C16—N2—C9 | 112.0 (2) | C3—C2—H2 | 120.6 (16) |
H5A—O5—H5B | 120 (5) | C10—C11—C12 | 117.1 (3) |
C5—C6—N1 | 119.7 (2) | C10—C11—H11 | 121.4 (19) |
C5—C6—C1 | 121.7 (2) | C12—C11—H11 | 121.5 (18) |
C1—C6—N1 | 118.6 (2) | C1—C17—C18 | 116.4 (3) |
S1—C7—H7A | 106.2 (13) | C1—C17—H17A | 104.8 (17) |
S1—C7—H7B | 104.5 (13) | C1—C17—H17B | 107.6 (17) |
C8—C7—S1 | 113.0 (2) | C18—C17—H17A | 108.3 (17) |
C8—C7—H7A | 113.9 (14) | C18—C17—H17B | 110.6 (18) |
C8—C7—H7B | 111.8 (14) | H17A—C17—H17B | 109 (3) |
H7A—C7—H7B | 107 (2) | C15—C14—C13 | 117.7 (4) |
C10—C15—C16 | 108.1 (2) | C15—C14—H14 | 119.3 (17) |
C14—C15—C10 | 120.7 (3) | C13—C14—H14 | 123.0 (17) |
C14—C15—C16 | 131.1 (3) | C4—C3—C2 | 120.5 (3) |
C6—C5—H5 | 118.5 (16) | C4—C3—H3 | 120.2 (18) |
C4—C5—C6 | 120.2 (3) | C2—C3—H3 | 119.3 (18) |
C4—C5—H5 | 121.3 (16) | C14—C13—H13 | 119.7 (17) |
N2—C8—C7 | 111.5 (2) | C12—C13—C14 | 121.5 (3) |
N2—C8—H8A | 105.2 (14) | C12—C13—H13 | 118.9 (17) |
N2—C8—H8B | 105.1 (14) | C17—C18—H18A | 109.5 |
C7—C8—H8A | 110.1 (15) | C17—C18—H18B | 109.5 |
C7—C8—H8B | 114.6 (15) | C17—C18—H18C | 109.5 |
H8A—C8—H8B | 110 (2) | H18A—C18—H18B | 109.5 |
C15—C10—C9 | 107.9 (2) | H18A—C18—H18C | 109.5 |
C11—C10—C15 | 121.6 (3) | H18B—C18—H18C | 109.5 |
C11—C10—C9 | 130.4 (3) | C11—C12—H12 | 118.5 (19) |
O3—C9—N2 | 124.1 (2) | C13—C12—C11 | 121.3 (3) |
O3—C9—C10 | 130.2 (3) | C13—C12—H12 | 120.2 (19) |
N2—C9—C10 | 105.7 (2) | | |
| | | |
S1—N1—C6—C5 | 88.4 (3) | C10—C15—C16—N2 | 0.7 (3) |
S1—N1—C6—C1 | −93.8 (3) | C10—C15—C16—O4 | −179.1 (3) |
S1—C7—C8—N2 | 175.6 (2) | C10—C15—C14—C13 | −0.4 (5) |
O1—S1—N1—C6 | 47.0 (2) | C10—C11—C12—C13 | −0.2 (6) |
O1—S1—C7—C8 | 177.2 (2) | C9—N2—C8—C7 | −89.4 (3) |
O2—S1—N1—C6 | 177.2 (2) | C9—N2—C16—O4 | 179.1 (3) |
O2—S1—C7—C8 | 47.7 (3) | C9—N2—C16—C15 | −0.7 (3) |
N1—S1—C7—C8 | −66.8 (3) | C9—C10—C11—C12 | −177.3 (3) |
N1—C6—C5—C4 | 178.4 (3) | C1—C6—C5—C4 | 0.6 (4) |
N1—C6—C1—C2 | −178.3 (3) | C1—C2—C3—C4 | 0.5 (5) |
N1—C6—C1—C17 | 0.9 (4) | C16—N2—C8—C7 | 92.5 (3) |
C6—C5—C4—C3 | −0.1 (5) | C16—N2—C9—O3 | −179.0 (3) |
C6—C1—C2—C3 | 0.0 (5) | C16—N2—C9—C10 | 0.4 (3) |
C6—C1—C17—C18 | −166.9 (3) | C16—C15—C10—C9 | −0.5 (3) |
C7—S1—N1—C6 | −67.8 (3) | C16—C15—C10—C11 | −178.7 (3) |
C15—C10—C9—O3 | 179.4 (3) | C16—C15—C14—C13 | 177.7 (3) |
C15—C10—C9—N2 | 0.1 (3) | C2—C1—C17—C18 | 12.2 (5) |
C15—C10—C11—C12 | 0.5 (5) | C11—C10—C9—O3 | −2.6 (5) |
C15—C14—C13—C12 | 0.7 (6) | C11—C10—C9—N2 | 178.1 (3) |
C5—C6—C1—C2 | −0.5 (4) | C17—C1—C2—C3 | −179.2 (3) |
C5—C6—C1—C17 | 178.6 (3) | C14—C15—C10—C9 | 178.1 (3) |
C5—C4—C3—C2 | −0.4 (5) | C14—C15—C10—C11 | −0.1 (5) |
C8—N2—C9—O3 | 2.7 (4) | C14—C15—C16—N2 | −177.6 (3) |
C8—N2—C9—C10 | −177.9 (2) | C14—C15—C16—O4 | 2.5 (6) |
C8—N2—C16—O4 | −2.6 (5) | C14—C13—C12—C11 | −0.3 (6) |
C8—N2—C16—C15 | 177.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3 | 0.98 (3) | 2.57 (3) | 3.482 (3) | 154 (2) |
N1—H1···O5 | 0.78 (3) | 2.00 (3) | 2.786 (4) | 176 (2) |
O5—H5A···O3i | 0.94 (6) | 2.03 (6) | 2.862 (5) | 146 (5) |
C17—H17B···O1 | 1.00 (3) | 2.55 (3) | 3.285 (4) | 130 (2) |
O5—H5B···O4ii | 0.70 (4) | 2.37 (4) | 2.943 (4) | 140 (5) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.