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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, C16H14N2O4S, (I), and the N-(4-nitro­phen­yl)-, C16H13N3O6S, (II), N-(4-meth­oxy­phen­yl)-, C16H16N3O6S, (III), and N-(2-ethyl­phen­yl)-, as the monohydrate, C18H18N2O4S·H2O, (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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017442/fn3251sup1.cif
Contains datablocks I, II, III, IV, paper

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017442/fn3251isup2.hkl
Contains datablock i

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017442/fn3251ivsup5.hkl
Contains datablock iv

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017442/fn3251Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017442/fn3251IIsup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017442/fn3251IIIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617017442/fn3251IVsup7.cml
Supplementary material

CCDC references: 1589303; 1589302; 1589301; 1589300

Computing details top

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
C16H14N2O4SZ = 2
Mr = 330.35F(000) = 344
Triclinic, P1Dx = 1.443 Mg m3
a = 6.9783 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7631 (7) ÅCell parameters from 1691 reflections
c = 11.8912 (9) Åθ = 3.9–28.6°
α = 78.365 (6)°µ = 0.24 mm1
β = 74.458 (6)°T = 293 K
γ = 81.063 (6)°Needle, colourless
V = 760.06 (10) Å30.65 × 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-1Rint = 0.017
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: analytical
[CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)]
h = 88
Tmin = 0.981, Tmax = 0.998k = 1111
5228 measured reflectionsl = 1413
2691 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039All 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 reflectionsΔρmax = 0.22 e Å3
264 parametersΔρmin = 0.36 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.17173 (9)0.61707 (6)0.27867 (5)0.0454 (2)
O30.5551 (2)0.26502 (16)0.45734 (13)0.0525 (4)
O10.0169 (2)0.62170 (17)0.36395 (14)0.0605 (5)
O40.6874 (3)0.43478 (16)0.06206 (13)0.0580 (5)
N20.6061 (2)0.38323 (17)0.26525 (14)0.0383 (4)
O20.2268 (3)0.74129 (16)0.19703 (15)0.0634 (5)
N10.1816 (3)0.50160 (19)0.19698 (17)0.0442 (5)
C60.1616 (3)0.3564 (2)0.23602 (18)0.0374 (5)
C150.6942 (3)0.1932 (2)0.16803 (18)0.0389 (5)
C100.6515 (3)0.1420 (2)0.28889 (18)0.0381 (5)
C90.5980 (3)0.2631 (2)0.35246 (18)0.0390 (5)
C160.6663 (3)0.3489 (2)0.15228 (18)0.0407 (5)
C50.2178 (3)0.2688 (3)0.1518 (2)0.0470 (6)
C10.0941 (3)0.2995 (2)0.3539 (2)0.0469 (6)
C110.6608 (3)0.0002 (2)0.3317 (2)0.0485 (6)
C80.5672 (4)0.5260 (2)0.2905 (2)0.0469 (6)
C70.3544 (4)0.5604 (3)0.3617 (2)0.0458 (5)
C140.7484 (4)0.1044 (3)0.0862 (2)0.0545 (6)
C20.0904 (4)0.1550 (3)0.3863 (2)0.0567 (6)
C40.2101 (4)0.1253 (3)0.1872 (3)0.0550 (6)
C120.7156 (4)0.0900 (3)0.2492 (2)0.0572 (6)
C130.7593 (4)0.0386 (3)0.1295 (3)0.0613 (7)
C30.1488 (4)0.0682 (3)0.3038 (3)0.0569 (7)
H10.233 (3)0.525 (3)0.131 (2)0.049 (7)*
H50.270 (3)0.302 (2)0.071 (2)0.055 (7)*
H140.778 (4)0.138 (3)0.002 (2)0.066 (8)*
H1A0.053 (3)0.354 (2)0.409 (2)0.052 (7)*
H7A0.312 (3)0.482 (2)0.421 (2)0.048 (6)*
H8A0.604 (3)0.587 (2)0.214 (2)0.054 (7)*
H7B0.348 (3)0.643 (3)0.398 (2)0.064 (7)*
H110.633 (3)0.032 (2)0.412 (2)0.062 (7)*
H20.054 (4)0.125 (3)0.471 (3)0.079 (8)*
H40.255 (3)0.073 (3)0.126 (2)0.061 (7)*
H120.726 (4)0.190 (3)0.276 (2)0.083 (9)*
H8B0.661 (4)0.538 (3)0.336 (2)0.066 (7)*
H30.142 (4)0.029 (3)0.330 (2)0.077 (8)*
H130.791 (4)0.105 (3)0.073 (3)0.085 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0644 (4)0.0341 (3)0.0371 (3)0.0038 (2)0.0152 (3)0.0079 (2)
O30.0736 (11)0.0541 (10)0.0316 (9)0.0110 (8)0.0163 (8)0.0034 (7)
O10.0626 (10)0.0633 (11)0.0480 (10)0.0156 (8)0.0079 (8)0.0166 (8)
O40.0834 (12)0.0464 (10)0.0348 (9)0.0059 (8)0.0076 (8)0.0047 (7)
N20.0464 (10)0.0352 (10)0.0335 (9)0.0071 (7)0.0108 (8)0.0029 (8)
O20.1049 (14)0.0324 (9)0.0519 (10)0.0046 (8)0.0239 (10)0.0004 (8)
N10.0659 (13)0.0389 (11)0.0279 (10)0.0082 (9)0.0109 (9)0.0044 (8)
C60.0394 (11)0.0381 (13)0.0365 (11)0.0044 (9)0.0121 (9)0.0064 (9)
C150.0397 (11)0.0407 (12)0.0339 (11)0.0002 (9)0.0087 (9)0.0044 (9)
C100.0369 (11)0.0382 (13)0.0374 (11)0.0033 (9)0.0105 (9)0.0013 (9)
C90.0396 (11)0.0433 (13)0.0354 (12)0.0083 (9)0.0136 (9)0.0006 (10)
C160.0412 (12)0.0439 (13)0.0343 (12)0.0053 (9)0.0078 (9)0.0022 (10)
C50.0545 (14)0.0516 (15)0.0383 (13)0.0089 (11)0.0128 (11)0.0110 (11)
C10.0518 (13)0.0467 (14)0.0408 (13)0.0100 (10)0.0057 (10)0.0084 (11)
C110.0514 (13)0.0435 (15)0.0455 (14)0.0026 (10)0.0126 (11)0.0029 (11)
C80.0609 (15)0.0391 (13)0.0459 (14)0.0155 (11)0.0177 (12)0.0048 (11)
C70.0667 (15)0.0397 (13)0.0364 (12)0.0048 (11)0.0177 (11)0.0126 (11)
C140.0626 (15)0.0552 (17)0.0411 (14)0.0043 (12)0.0094 (12)0.0104 (12)
C20.0604 (15)0.0521 (16)0.0532 (16)0.0190 (12)0.0096 (12)0.0052 (13)
C40.0599 (15)0.0480 (16)0.0639 (17)0.0067 (11)0.0167 (13)0.0219 (14)
C120.0644 (16)0.0378 (15)0.0661 (17)0.0030 (11)0.0167 (13)0.0064 (13)
C130.0758 (18)0.0465 (16)0.0601 (17)0.0089 (13)0.0161 (14)0.0183 (14)
C30.0597 (15)0.0405 (15)0.0708 (19)0.0116 (12)0.0158 (13)0.0051 (13)
Geometric parameters (Å, º) top
S1—O11.4309 (17)C1—C21.388 (3)
S1—O21.4252 (17)C1—H1A0.88 (2)
S1—N11.6128 (19)C11—C121.389 (4)
S1—C71.772 (2)C11—H110.93 (2)
O3—C91.205 (2)C8—C71.523 (3)
O4—C161.211 (2)C8—H8A0.98 (2)
N2—C91.398 (3)C8—H8B0.99 (3)
N2—C161.389 (3)C7—H7A0.96 (2)
N2—C81.454 (3)C7—H7B0.98 (3)
N1—C61.416 (3)C14—C131.385 (4)
N1—H10.78 (2)C14—H140.97 (3)
C6—C51.385 (3)C2—C31.364 (4)
C6—C11.382 (3)C2—H20.96 (3)
C15—C101.390 (3)C4—C31.364 (4)
C15—C161.483 (3)C4—H40.93 (2)
C15—C141.372 (3)C12—C131.378 (4)
C10—C91.477 (3)C12—H120.96 (3)
C10—C111.372 (3)C13—H130.98 (3)
C5—C41.384 (3)C3—H30.95 (3)
C5—H50.94 (2)
O1—S1—N1109.59 (11)C10—C11—C12117.2 (2)
O1—S1—C7105.69 (11)C10—C11—H11120.5 (15)
O2—S1—O1119.21 (11)C12—C11—H11122.2 (15)
O2—S1—N1104.80 (10)N2—C8—C7113.04 (19)
O2—S1—C7108.76 (12)N2—C8—H8A105.8 (13)
N1—S1—C7108.48 (10)N2—C8—H8B108.7 (14)
C9—N2—C8123.78 (17)C7—C8—H8A114.5 (13)
C16—N2—C9111.55 (16)C7—C8—H8B108.6 (15)
C16—N2—C8124.58 (17)H8A—C8—H8B105.8 (19)
S1—N1—H1113.4 (18)S1—C7—H7A108.9 (13)
C6—N1—S1126.66 (16)S1—C7—H7B101.1 (14)
C6—N1—H1117.2 (18)C8—C7—S1115.95 (16)
C5—C6—N1117.89 (19)C8—C7—H7A110.6 (13)
C1—C6—N1122.7 (2)C8—C7—H7B109.4 (14)
C1—C6—C5119.4 (2)H7A—C7—H7B110.4 (18)
C10—C15—C16107.72 (18)C15—C14—C13117.0 (2)
C14—C15—C10121.5 (2)C15—C14—H14122.4 (15)
C14—C15—C16130.8 (2)C13—C14—H14120.5 (15)
C15—C10—C9108.26 (18)C1—C2—H2113.0 (17)
C11—C10—C15121.5 (2)C3—C2—C1121.3 (3)
C11—C10—C9130.3 (2)C3—C2—H2125.5 (17)
O3—C9—N2124.30 (19)C5—C4—H4114.8 (15)
O3—C9—C10129.64 (19)C3—C4—C5121.1 (2)
N2—C9—C10106.06 (17)C3—C4—H4124.0 (15)
O4—C16—N2124.0 (2)C11—C12—H12119.7 (17)
O4—C16—C15129.6 (2)C13—C12—C11121.1 (3)
N2—C16—C15106.37 (17)C13—C12—H12119.3 (17)
C6—C5—H5122.7 (14)C14—C13—H13118.7 (17)
C4—C5—C6119.6 (2)C12—C13—C14121.7 (3)
C4—C5—H5117.6 (14)C12—C13—H13119.5 (17)
C6—C1—C2119.4 (2)C2—C3—C4119.1 (2)
C6—C1—H1A120.9 (16)C2—C3—H3118.2 (17)
C2—C1—H1A119.7 (16)C4—C3—H3122.7 (17)
S1—N1—C6—C5166.01 (17)C9—C10—C11—C12179.6 (2)
S1—N1—C6—C112.2 (3)C16—N2—C9—O3177.9 (2)
O1—S1—N1—C658.6 (2)C16—N2—C9—C102.0 (2)
O1—S1—C7—C8171.30 (17)C16—N2—C8—C7120.9 (2)
N2—C8—C7—S184.7 (2)C16—C15—C10—C90.6 (2)
O2—S1—N1—C6172.35 (18)C16—C15—C10—C11178.86 (18)
O2—S1—C7—C859.6 (2)C16—C15—C14—C13179.2 (2)
N1—S1—C7—C853.8 (2)C5—C6—C1—C22.2 (3)
N1—C6—C5—C4176.71 (19)C5—C4—C3—C21.3 (4)
N1—C6—C1—C2176.0 (2)C1—C6—C5—C41.6 (3)
C6—C5—C4—C30.2 (4)C1—C2—C3—C40.6 (4)
C6—C1—C2—C31.2 (4)C11—C10—C9—O32.3 (4)
C15—C10—C9—O3178.3 (2)C11—C10—C9—N2177.8 (2)
C15—C10—C9—N21.5 (2)C11—C12—C13—C140.7 (4)
C15—C10—C11—C120.3 (3)C8—N2—C9—O31.2 (3)
C15—C14—C13—C120.7 (4)C8—N2—C9—C10178.65 (18)
C10—C15—C16—O4180.0 (2)C8—N2—C16—O42.3 (3)
C10—C15—C16—N20.6 (2)C8—N2—C16—C15178.29 (18)
C10—C15—C14—C130.1 (3)C7—S1—N1—C656.3 (2)
C10—C11—C12—C130.2 (4)C14—C15—C10—C9179.80 (19)
C9—N2—C16—O4178.97 (19)C14—C15—C10—C110.4 (3)
C9—N2—C16—C151.6 (2)C14—C15—C16—O40.8 (4)
C9—N2—C8—C762.9 (3)C14—C15—C16—N2178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O10.88 (2)2.56 (2)3.139 (3)124.1 (19)
C7—H7A···O30.96 (2)2.54 (2)3.138 (3)120.5 (16)
N1—H1···O4i0.78 (2)2.18 (3)2.934 (3)165 (2)
C14—H14···O2i0.97 (3)2.43 (3)3.372 (3)166 (2)
C7—H7B···O3ii0.98 (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
C16H13N3O6SZ = 2
Mr = 375.35F(000) = 388
Triclinic, P1Dx = 1.535 Mg m3
a = 7.1547 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4322 (13) ÅCell parameters from 2023 reflections
c = 11.8228 (16) Åθ = 3.8–28.1°
α = 100.106 (11)°µ = 0.24 mm1
β = 104.043 (10)°T = 293 K
γ = 102.278 (9)°Needle, colourless
V = 812.13 (18) Å30.38 × 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-1Rint = 0.023
ω scansθmax = 29.2°, θmin = 3.1°
Absorption correction: analytical
[CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)]
h = 89
Tmin = 0.975, Tmax = 0.996k = 1414
6276 measured reflectionsl = 1513
3661 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044All 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 reflectionsΔρmax = 0.20 e Å3
287 parametersΔρmin = 0.38 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.02375 (7)0.68705 (5)0.22465 (5)0.03721 (16)
O30.3869 (2)0.48939 (14)0.08869 (13)0.0463 (4)
O10.9877 (2)0.77992 (13)0.15224 (14)0.0520 (4)
O21.2246 (2)0.68924 (14)0.28361 (14)0.0523 (4)
N20.5825 (2)0.53496 (14)0.28430 (14)0.0321 (4)
O40.7162 (2)0.51754 (15)0.47671 (13)0.0530 (4)
N10.9084 (2)0.53973 (16)0.13394 (16)0.0364 (4)
O60.8477 (3)0.02247 (17)0.33970 (18)0.0755 (6)
O50.6553 (3)0.06541 (15)0.15958 (18)0.0732 (6)
N30.7711 (3)0.03078 (18)0.2381 (2)0.0528 (5)
C60.8888 (3)0.41276 (17)0.16100 (17)0.0308 (4)
C90.4434 (3)0.45195 (19)0.17894 (18)0.0334 (4)
C50.9857 (3)0.3961 (2)0.27215 (19)0.0364 (5)
C160.6096 (3)0.46676 (19)0.37550 (18)0.0350 (4)
C30.8185 (3)0.16204 (18)0.20971 (19)0.0381 (5)
C150.4859 (3)0.32587 (18)0.32164 (19)0.0354 (4)
C40.9491 (3)0.2713 (2)0.2970 (2)0.0392 (5)
C80.6780 (3)0.67750 (19)0.3000 (2)0.0379 (5)
C70.9054 (3)0.7101 (2)0.33982 (19)0.0366 (5)
C10.7635 (3)0.3002 (2)0.07222 (19)0.0369 (5)
C100.3876 (3)0.31708 (18)0.20339 (18)0.0341 (4)
C20.7293 (3)0.1755 (2)0.0967 (2)0.0408 (5)
C110.2656 (3)0.1960 (2)0.1282 (2)0.0446 (5)
C120.2454 (4)0.0841 (2)0.1751 (3)0.0533 (6)
C140.4662 (3)0.2144 (2)0.3698 (3)0.0508 (6)
C130.3428 (4)0.0925 (2)0.2934 (3)0.0574 (7)
H1A0.705 (3)0.3160 (18)0.0030 (18)0.040 (6)*
H51.077 (3)0.470 (2)0.3308 (19)0.049 (6)*
H7A0.951 (3)0.6593 (17)0.3925 (16)0.027 (5)*
H10.829 (3)0.545 (2)0.0698 (19)0.042 (6)*
H8A0.627 (3)0.6983 (19)0.2222 (19)0.041 (6)*
H41.011 (3)0.2574 (19)0.3755 (19)0.041 (6)*
H7B0.957 (3)0.807 (2)0.3730 (18)0.044 (6)*
H20.645 (3)0.101 (2)0.037 (2)0.054 (6)*
H140.538 (3)0.222 (2)0.452 (2)0.054 (7)*
H110.204 (3)0.191 (2)0.049 (2)0.055 (7)*
H130.330 (3)0.014 (2)0.324 (2)0.057 (7)*
H8B0.635 (3)0.728 (2)0.362 (2)0.057 (7)*
H120.167 (4)0.007 (3)0.125 (2)0.083 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0314 (3)0.0326 (3)0.0407 (3)0.00170 (19)0.0070 (2)0.0086 (2)
O30.0451 (9)0.0511 (8)0.0352 (9)0.0055 (7)0.0005 (7)0.0160 (7)
O10.0634 (10)0.0365 (7)0.0523 (10)0.0009 (7)0.0139 (8)0.0205 (7)
O20.0267 (8)0.0585 (9)0.0589 (10)0.0001 (6)0.0048 (7)0.0066 (8)
N20.0284 (8)0.0306 (8)0.0319 (9)0.0033 (6)0.0035 (6)0.0067 (7)
O40.0500 (9)0.0616 (10)0.0331 (9)0.0011 (7)0.0010 (7)0.0128 (8)
N10.0381 (10)0.0333 (8)0.0304 (10)0.0052 (7)0.0003 (7)0.0077 (8)
O60.1075 (16)0.0548 (10)0.0703 (13)0.0262 (10)0.0192 (11)0.0346 (10)
O50.0769 (13)0.0327 (8)0.0942 (15)0.0045 (8)0.0059 (11)0.0138 (10)
N30.0568 (13)0.0417 (11)0.0677 (15)0.0205 (9)0.0205 (11)0.0208 (11)
C60.0269 (9)0.0316 (9)0.0322 (11)0.0072 (7)0.0071 (8)0.0065 (8)
C90.0264 (9)0.0399 (10)0.0318 (11)0.0066 (8)0.0073 (8)0.0075 (9)
C50.0338 (11)0.0342 (10)0.0351 (12)0.0094 (8)0.0018 (9)0.0035 (9)
C160.0294 (10)0.0424 (10)0.0321 (11)0.0066 (8)0.0075 (8)0.0118 (9)
C30.0364 (11)0.0321 (10)0.0486 (13)0.0128 (8)0.0137 (9)0.0107 (10)
C150.0311 (10)0.0355 (10)0.0411 (12)0.0059 (8)0.0128 (9)0.0135 (9)
C40.0404 (11)0.0426 (11)0.0353 (12)0.0178 (9)0.0062 (9)0.0099 (10)
C80.0356 (11)0.0294 (10)0.0460 (14)0.0065 (8)0.0089 (10)0.0090 (10)
C70.0347 (11)0.0284 (10)0.0377 (12)0.0023 (8)0.0030 (9)0.0030 (9)
C10.0341 (11)0.0386 (10)0.0317 (12)0.0077 (8)0.0018 (8)0.0054 (9)
C100.0264 (10)0.0356 (10)0.0386 (12)0.0041 (8)0.0115 (8)0.0064 (9)
C20.0371 (11)0.0322 (10)0.0447 (13)0.0061 (9)0.0051 (9)0.0010 (10)
C110.0364 (12)0.0409 (11)0.0469 (14)0.0012 (9)0.0115 (10)0.0013 (11)
C120.0475 (14)0.0368 (12)0.0722 (19)0.0013 (10)0.0237 (13)0.0078 (13)
C140.0456 (13)0.0547 (14)0.0592 (17)0.0128 (11)0.0180 (12)0.0288 (13)
C130.0541 (15)0.0376 (12)0.092 (2)0.0088 (11)0.0330 (14)0.0315 (14)
Geometric parameters (Å, º) top
S1—O11.4240 (15)C3—C21.379 (3)
S1—O21.4303 (14)C15—C101.381 (3)
S1—N11.6267 (17)C15—C141.378 (3)
S1—C71.778 (2)C4—H40.98 (2)
O3—C91.208 (2)C8—C71.523 (3)
N2—C91.395 (2)C8—H8A0.98 (2)
N2—C161.390 (2)C8—H8B0.98 (2)
N2—C81.457 (2)C7—H7A0.931 (17)
O4—C161.207 (2)C7—H7B0.973 (19)
N1—C61.403 (2)C1—C21.366 (3)
N1—H10.85 (2)C1—H1A0.946 (19)
O6—N31.220 (3)C10—C111.382 (3)
O5—N31.225 (2)C2—H20.93 (2)
N3—C31.457 (3)C11—C121.373 (3)
C6—C51.388 (3)C11—H110.92 (2)
C6—C11.396 (3)C12—C131.381 (4)
C9—C101.477 (3)C12—H120.99 (3)
C5—C41.370 (3)C14—C131.395 (3)
C5—H50.94 (2)C14—H140.97 (2)
C16—C151.481 (3)C13—H130.95 (2)
C3—C41.379 (3)
O1—S1—O2119.81 (9)C3—C4—H4118.7 (12)
O1—S1—N1103.98 (9)N2—C8—C7112.68 (15)
O1—S1—C7108.73 (10)N2—C8—H8A105.7 (12)
O2—S1—N1109.83 (9)N2—C8—H8B107.0 (13)
O2—S1—C7105.94 (10)C7—C8—H8A112.0 (12)
N1—S1—C7108.14 (9)C7—C8—H8B108.6 (13)
C9—N2—C8124.61 (16)H8A—C8—H8B110.8 (16)
C16—N2—C9111.40 (15)S1—C7—H7A105.8 (11)
C16—N2—C8123.88 (17)S1—C7—H7B100.8 (12)
S1—N1—H1112.3 (14)C8—C7—S1116.75 (15)
C6—N1—S1127.68 (15)C8—C7—H7A111.9 (11)
C6—N1—H1118.0 (14)C8—C7—H7B107.8 (11)
O6—N3—O5123.2 (2)H7A—C7—H7B113.4 (16)
O6—N3—C3118.1 (2)C6—C1—H1A116.5 (11)
O5—N3—C3118.7 (2)C2—C1—C6120.1 (2)
C5—C6—N1122.62 (17)C2—C1—H1A123.4 (12)
C5—C6—C1119.53 (18)C15—C10—C9108.26 (16)
C1—C6—N1117.84 (18)C15—C10—C11121.4 (2)
O3—C9—N2124.12 (17)C11—C10—C9130.3 (2)
O3—C9—C10129.82 (18)C3—C2—H2121.1 (14)
N2—C9—C10106.05 (16)C1—C2—C3119.51 (19)
C6—C5—H5120.2 (12)C1—C2—H2119.4 (14)
C4—C5—C6120.19 (19)C10—C11—H11120.3 (14)
C4—C5—H5119.6 (12)C12—C11—C10117.6 (2)
N2—C16—C15106.20 (16)C12—C11—H11122.1 (14)
O4—C16—N2124.40 (18)C11—C12—C13121.2 (2)
O4—C16—C15129.40 (19)C11—C12—H12121.7 (15)
C4—C3—N3119.4 (2)C13—C12—H12117.0 (15)
C2—C3—N3119.41 (19)C15—C14—C13116.8 (2)
C2—C3—C4121.15 (19)C15—C14—H14120.6 (13)
C10—C15—C16107.95 (17)C13—C14—H14122.6 (13)
C14—C15—C16130.5 (2)C12—C13—C14121.5 (2)
C14—C15—C10121.5 (2)C12—C13—H13120.3 (14)
C5—C4—C3119.4 (2)C14—C13—H13118.2 (14)
C5—C4—H4121.9 (12)
S1—N1—C6—C56.1 (3)C9—N2—C16—O4177.00 (18)
S1—N1—C6—C1172.77 (15)C9—N2—C16—C153.5 (2)
O3—C9—C10—C15177.44 (19)C9—N2—C8—C7124.43 (19)
O3—C9—C10—C114.3 (3)C9—C10—C11—C12177.97 (18)
O1—S1—N1—C6176.98 (16)C5—C6—C1—C23.2 (3)
O1—S1—C7—C864.70 (17)C16—N2—C9—O3176.31 (17)
O2—S1—N1—C653.64 (19)C16—N2—C9—C103.9 (2)
O2—S1—C7—C8165.30 (14)C16—N2—C8—C759.9 (2)
N2—C9—C10—C152.83 (19)C16—C15—C10—C90.8 (2)
N2—C9—C10—C11175.39 (19)C16—C15—C10—C11177.63 (17)
N2—C16—C15—C101.6 (2)C16—C15—C14—C13177.10 (19)
N2—C16—C15—C14176.0 (2)C15—C10—C11—C120.0 (3)
N2—C8—C7—S185.6 (2)C15—C14—C13—C120.1 (3)
O4—C16—C15—C10178.9 (2)C4—C3—C2—C13.0 (3)
O4—C16—C15—C143.5 (4)C8—N2—C9—O30.1 (3)
N1—S1—C7—C847.60 (17)C8—N2—C9—C10179.89 (16)
N1—C6—C5—C4174.84 (17)C8—N2—C16—O40.8 (3)
N1—C6—C1—C2175.77 (17)C8—N2—C16—C15179.68 (16)
O6—N3—C3—C40.9 (3)C7—S1—N1—C661.54 (18)
O6—N3—C3—C2178.0 (2)C1—C6—C5—C44.0 (3)
O5—N3—C3—C4179.81 (19)C10—C15—C14—C130.1 (3)
O5—N3—C3—C21.3 (3)C10—C11—C12—C130.3 (3)
N3—C3—C4—C5176.70 (17)C2—C3—C4—C52.1 (3)
N3—C3—C2—C1175.83 (17)C11—C12—C13—C140.3 (4)
C6—C5—C4—C31.4 (3)C14—C15—C10—C9178.57 (17)
C6—C1—C2—C30.3 (3)C14—C15—C10—C110.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O20.94 (2)2.52 (2)3.132 (3)123.0 (15)
C7—H7A···O40.931 (17)2.505 (18)3.088 (3)120.9 (13)
C5—H5···O4i0.94 (2)2.36 (2)3.057 (3)130.6 (15)
N1—H1···O3ii0.85 (2)2.04 (2)2.869 (2)166 (2)
C1—H1A···O3ii0.946 (19)2.558 (19)3.328 (3)138.7 (14)
C11—H11···O1ii0.92 (2)2.55 (2)3.451 (3)168.6 (18)
C7—H7B···O6iii0.973 (19)2.594 (19)3.371 (3)136.9 (15)
C12—H12···O1iv0.99 (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) x1, y1, z.
N-(4-Methoxyphenyl)-2-phthalimidoethanesulfonamide (III) top
Crystal data top
C17H16N2O5SF(000) = 752
Mr = 360.38Dx = 1.444 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.9408 (9) ÅCell parameters from 1361 reflections
b = 7.2555 (7) Åθ = 3.8–27.6°
c = 21.1923 (18) ŵ = 0.23 mm1
β = 99.838 (8)°T = 293 K
V = 1657.5 (3) Å3Needle, colourless
Z = 40.53 × 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-1Rint = 0.019
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: analytical
[CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)]
h = 913
Tmin = 0.979, Tmax = 0.997k = 48
5141 measured reflectionsl = 1825
2907 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038All 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 reflectionsΔρmax = 0.13 e Å3
290 parametersΔρmin = 0.31 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.43556 (4)0.54727 (8)0.59432 (2)0.04821 (18)
O51.00320 (13)0.5216 (2)0.76716 (7)0.0621 (5)
O20.35392 (13)0.4831 (2)0.53852 (7)0.0641 (5)
O10.40466 (13)0.5129 (2)0.65539 (7)0.0654 (5)
O40.10455 (15)0.7307 (3)0.58806 (8)0.0753 (5)
N20.24268 (15)0.8706 (3)0.53338 (8)0.0507 (5)
O30.33224 (14)1.0018 (3)0.45398 (9)0.0794 (6)
N10.56844 (17)0.4530 (3)0.59052 (10)0.0609 (6)
C100.12470 (18)0.8725 (3)0.43301 (10)0.0466 (5)
C150.05539 (17)0.7886 (3)0.47369 (10)0.0474 (5)
C160.13006 (19)0.7881 (3)0.53876 (11)0.0519 (5)
C30.89736 (17)0.5165 (3)0.72260 (9)0.0452 (5)
C40.88529 (19)0.5988 (3)0.66360 (10)0.0473 (5)
C60.67772 (18)0.4833 (3)0.63749 (10)0.0467 (5)
C90.24536 (19)0.9256 (3)0.47103 (11)0.0522 (5)
C50.77489 (19)0.5823 (3)0.62138 (10)0.0498 (6)
C10.6900 (2)0.4030 (4)0.69689 (11)0.0567 (6)
C70.45669 (19)0.7861 (3)0.58534 (12)0.0534 (6)
C20.7984 (2)0.4204 (4)0.73947 (11)0.0578 (6)
C140.0624 (2)0.7243 (3)0.45135 (14)0.0603 (6)
C110.0783 (2)0.8943 (4)0.36898 (12)0.0592 (6)
C130.1085 (2)0.7452 (4)0.38774 (14)0.0666 (7)
C80.3417 (2)0.9009 (4)0.58732 (13)0.0620 (6)
C120.0406 (2)0.8295 (4)0.34698 (14)0.0664 (7)
C171.1070 (3)0.6182 (6)0.75024 (15)0.0731 (8)
H40.9516 (19)0.666 (3)0.6511 (9)0.058 (6)*
H50.7677 (17)0.639 (3)0.5809 (10)0.057 (6)*
H7A0.4918 (18)0.800 (3)0.5465 (10)0.060 (6)*
H1A0.626 (2)0.337 (3)0.7088 (10)0.062 (7)*
H7B0.519 (2)0.820 (3)0.6178 (11)0.066 (7)*
H140.1082 (19)0.666 (3)0.4782 (10)0.060 (7)*
H110.126 (2)0.947 (3)0.3418 (10)0.061 (7)*
H130.189 (2)0.703 (3)0.3715 (10)0.071 (7)*
H17A1.133 (2)0.569 (4)0.7127 (12)0.076 (8)*
H20.8088 (19)0.365 (3)0.7806 (11)0.068 (7)*
H8A0.305 (2)0.868 (3)0.6255 (11)0.072 (7)*
H17B1.169 (3)0.604 (4)0.7857 (13)0.089 (9)*
H120.076 (2)0.845 (4)0.2987 (12)0.080 (7)*
H10.583 (3)0.463 (4)0.5552 (13)0.085 (10)*
H8B0.369 (3)1.034 (4)0.5859 (13)0.102 (10)*
H17C1.086 (3)0.755 (5)0.7427 (15)0.126 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0349 (3)0.0580 (4)0.0499 (3)0.0043 (2)0.0022 (2)0.0011 (3)
O50.0430 (8)0.0877 (13)0.0516 (8)0.0047 (8)0.0030 (7)0.0096 (8)
O20.0424 (8)0.0764 (12)0.0678 (10)0.0062 (8)0.0071 (7)0.0159 (9)
O10.0547 (9)0.0825 (13)0.0608 (9)0.0013 (8)0.0154 (7)0.0228 (9)
O40.0704 (11)0.0883 (14)0.0737 (11)0.0066 (10)0.0314 (9)0.0097 (10)
N20.0393 (9)0.0503 (12)0.0621 (11)0.0022 (8)0.0072 (8)0.0057 (9)
O30.0487 (10)0.0961 (15)0.0922 (12)0.0251 (9)0.0084 (9)0.0315 (11)
N10.0444 (11)0.0797 (16)0.0559 (12)0.0074 (10)0.0008 (9)0.0103 (12)
C100.0370 (11)0.0376 (12)0.0659 (13)0.0030 (9)0.0106 (10)0.0043 (11)
C150.0350 (11)0.0392 (12)0.0702 (14)0.0026 (9)0.0151 (10)0.0012 (11)
C160.0448 (12)0.0450 (13)0.0698 (14)0.0025 (10)0.0207 (11)0.0027 (12)
C30.0372 (11)0.0519 (14)0.0454 (11)0.0048 (9)0.0034 (9)0.0010 (10)
C40.0402 (11)0.0519 (14)0.0515 (12)0.0003 (10)0.0126 (10)0.0072 (11)
C60.0368 (11)0.0521 (14)0.0491 (11)0.0064 (10)0.0014 (9)0.0013 (10)
C90.0387 (12)0.0455 (13)0.0730 (14)0.0004 (10)0.0112 (10)0.0103 (12)
C50.0444 (12)0.0627 (15)0.0426 (11)0.0045 (11)0.0086 (9)0.0077 (11)
C10.0411 (12)0.0641 (16)0.0653 (14)0.0036 (12)0.0098 (11)0.0175 (13)
C70.0392 (12)0.0632 (16)0.0545 (13)0.0133 (11)0.0012 (10)0.0044 (12)
C20.0485 (13)0.0719 (17)0.0523 (12)0.0013 (12)0.0064 (10)0.0231 (13)
C140.0416 (13)0.0500 (15)0.0924 (18)0.0027 (11)0.0199 (13)0.0024 (14)
C110.0539 (14)0.0543 (15)0.0700 (15)0.0040 (12)0.0121 (12)0.0076 (13)
C130.0383 (13)0.0583 (16)0.099 (2)0.0011 (12)0.0007 (13)0.0128 (15)
C80.0566 (15)0.0583 (17)0.0673 (16)0.0047 (13)0.0004 (12)0.0036 (14)
C120.0556 (15)0.0602 (16)0.0771 (17)0.0114 (13)0.0063 (13)0.0065 (14)
C170.0462 (15)0.105 (3)0.0650 (17)0.0168 (16)0.0008 (13)0.0030 (19)
Geometric parameters (Å, º) top
S1—O21.4324 (15)C6—C51.374 (3)
S1—O11.4145 (14)C6—C11.372 (3)
S1—N11.621 (2)C5—H50.94 (2)
S1—C71.763 (3)C1—C21.368 (3)
O5—C31.364 (2)C1—H1A0.92 (2)
O5—C171.431 (3)C7—C81.515 (3)
O4—C161.201 (2)C7—H7A0.97 (2)
N2—C161.392 (3)C7—H7B0.92 (2)
N2—C91.385 (3)C2—H20.95 (2)
N2—C81.451 (3)C14—C131.365 (3)
O3—C91.207 (2)C14—H140.92 (2)
N1—C61.436 (3)C11—C121.386 (3)
N1—H10.80 (3)C11—H110.93 (2)
C10—C151.383 (3)C13—C121.375 (4)
C10—C91.475 (3)C13—H130.94 (2)
C10—C111.374 (3)C8—H8A0.99 (2)
C15—C161.478 (3)C8—H8B1.01 (3)
C15—C141.376 (3)C12—H121.04 (2)
C3—C41.371 (3)C17—H17A0.96 (3)
C3—C21.385 (3)C17—H17B0.93 (3)
C4—C51.380 (3)C17—H17C1.03 (4)
C4—H40.95 (2)
O2—S1—N1105.06 (10)C6—C1—H1A120.9 (14)
O2—S1—C7107.77 (10)C2—C1—C6120.2 (2)
O1—S1—O2119.03 (10)C2—C1—H1A118.9 (14)
O1—S1—N1109.13 (11)S1—C7—H7A105.9 (14)
O1—S1—C7109.15 (11)S1—C7—H7B106.0 (15)
N1—S1—C7105.92 (11)C8—C7—S1114.37 (17)
C3—O5—C17117.11 (18)C8—C7—H7A114.6 (13)
C16—N2—C8123.57 (19)C8—C7—H7B110.4 (15)
C9—N2—C16111.43 (17)H7A—C7—H7B104.9 (17)
C9—N2—C8124.96 (18)C3—C2—H2118.3 (13)
S1—N1—H1110 (2)C1—C2—C3120.3 (2)
C6—N1—S1123.26 (16)C1—C2—H2121.4 (13)
C6—N1—H1111 (2)C15—C14—H14121.2 (14)
C15—C10—C9108.03 (19)C13—C14—C15118.0 (2)
C11—C10—C15121.1 (2)C13—C14—H14120.8 (13)
C11—C10—C9130.9 (2)C10—C11—C12117.4 (2)
C10—C15—C16107.94 (18)C10—C11—H11120.5 (14)
C14—C15—C10121.1 (2)C12—C11—H11122.0 (14)
C14—C15—C16131.0 (2)C14—C13—C12121.4 (2)
O4—C16—N2124.1 (2)C14—C13—H13119.4 (14)
O4—C16—C15129.7 (2)C12—C13—H13119.1 (14)
N2—C16—C15106.18 (18)N2—C8—C7114.0 (2)
O5—C3—C4123.89 (18)N2—C8—H8A104.9 (13)
O5—C3—C2116.32 (18)N2—C8—H8B107.7 (17)
C4—C3—C2119.78 (19)C7—C8—H8A110.1 (14)
C3—C4—C5119.4 (2)C7—C8—H8B106.0 (17)
C3—C4—H4121.3 (13)H8A—C8—H8B114 (2)
C5—C4—H4119.3 (12)C11—C12—H12117.8 (13)
C5—C6—N1119.72 (19)C13—C12—C11121.1 (3)
C1—C6—N1120.7 (2)C13—C12—H12121.2 (13)
C1—C6—C5119.43 (19)O5—C17—H17A112.7 (16)
N2—C9—C10106.42 (17)O5—C17—H17B103.9 (17)
O3—C9—N2124.3 (2)O5—C17—H17C110.5 (18)
O3—C9—C10129.3 (2)H17A—C17—H17B111 (2)
C4—C5—H5118.7 (12)H17A—C17—H17C108 (2)
C6—C5—C4120.9 (2)H17B—C17—H17C110 (3)
C6—C5—H5120.4 (12)
S1—N1—C6—C5110.8 (2)C4—C3—C2—C11.8 (4)
S1—N1—C6—C174.0 (3)C6—C1—C2—C31.1 (4)
S1—C7—C8—N266.9 (3)C9—N2—C16—O4179.1 (2)
O5—C3—C4—C5178.6 (2)C9—N2—C16—C150.9 (2)
O5—C3—C2—C1177.8 (2)C9—N2—C8—C770.2 (3)
O2—S1—N1—C6179.29 (19)C9—C10—C15—C160.6 (2)
O2—S1—C7—C867.78 (19)C9—C10—C15—C14179.92 (19)
O1—S1—N1—C652.0 (2)C9—C10—C11—C12179.8 (2)
O1—S1—C7—C862.81 (19)C5—C6—C1—C20.5 (4)
N1—S1—C7—C8179.82 (17)C1—C6—C5—C41.4 (3)
N1—C6—C5—C4173.9 (2)C7—S1—N1—C665.4 (2)
N1—C6—C1—C2174.7 (2)C2—C3—C4—C51.0 (3)
C10—C15—C16—O4179.2 (2)C14—C15—C16—O40.1 (4)
C10—C15—C16—N20.9 (2)C14—C15—C16—N2179.8 (2)
C10—C15—C14—C130.3 (3)C14—C13—C12—C110.9 (4)
C10—C11—C12—C130.6 (4)C11—C10—C15—C16179.4 (2)
C15—C10—C9—N20.0 (2)C11—C10—C15—C140.1 (3)
C15—C10—C9—O3180.0 (2)C11—C10—C9—N2180.0 (2)
C15—C10—C11—C120.2 (3)C11—C10—C9—O30.0 (4)
C15—C14—C13—C120.7 (4)C8—N2—C16—O41.6 (3)
C16—N2—C9—O3179.4 (2)C8—N2—C16—C15178.47 (19)
C16—N2—C9—C100.6 (2)C8—N2—C9—O31.9 (4)
C16—N2—C8—C7112.6 (2)C8—N2—C9—C10178.10 (19)
C16—C15—C14—C13179.5 (2)C17—O5—C3—C40.4 (3)
C3—C4—C5—C60.6 (3)C17—O5—C3—C2179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.95 (2)2.36 (2)3.247 (3)155.7 (17)
C7—H7A···O3ii0.97 (2)2.40 (2)3.009 (3)120.0 (16)
N1—H1···O2iii0.80 (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.
(IV) top
Crystal data top
C18H18N2O4S·H2OF(000) = 792
Mr = 376.42Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.356 (3) ÅCell parameters from 1635 reflections
b = 7.4014 (5) Åθ = 3.8–25.8°
c = 25.061 (5) ŵ = 0.21 mm1
β = 141.36 (4)°T = 293 K
V = 1778.6 (11) Å3Prism, colourless
Z = 40.23 × 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-1Rint = 0.043
ω scansθmax = 29.1°, θmin = 3.1°
Absorption correction: analytical
[CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)]
h = 2019
Tmin = 0.992, Tmax = 0.996k = 109
8757 measured reflectionsl = 3432
4113 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H 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 reflectionsΔρmax = 0.21 e Å3
304 parametersΔρmin = 0.34 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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
xyzUiso*/Ueq
S10.28266 (7)0.75110 (11)0.52435 (4)0.0430 (2)
O10.32461 (19)0.9159 (3)0.51933 (12)0.0576 (6)
O20.16137 (17)0.6587 (3)0.44811 (10)0.0600 (6)
O30.4185 (2)0.6094 (3)0.76957 (12)0.0615 (6)
N10.4091 (2)0.6104 (4)0.58053 (14)0.0410 (6)
N20.1944 (2)0.6865 (3)0.63929 (13)0.0430 (6)
O40.0320 (2)0.7845 (3)0.53337 (12)0.0702 (7)
O50.3241 (4)0.2695 (4)0.5741 (2)0.0750 (8)
C60.5516 (2)0.6568 (4)0.66143 (15)0.0370 (6)
C70.2565 (3)0.8028 (4)0.5804 (2)0.0414 (7)
C150.1114 (3)0.7677 (4)0.68157 (17)0.0476 (7)
C50.5989 (3)0.6385 (4)0.73563 (18)0.0442 (7)
C80.2044 (3)0.6432 (5)0.5874 (2)0.0470 (8)
C100.2489 (3)0.7153 (4)0.75395 (17)0.0471 (8)
C90.3040 (3)0.6621 (4)0.72741 (17)0.0457 (7)
C10.6392 (3)0.7135 (4)0.66228 (16)0.0430 (7)
C160.0761 (3)0.7507 (4)0.60765 (18)0.0475 (7)
C40.7352 (3)0.6779 (4)0.8132 (2)0.0524 (8)
C20.7764 (3)0.7518 (5)0.74201 (19)0.0546 (8)
C110.3108 (4)0.7133 (5)0.8328 (2)0.0635 (10)
C170.5864 (3)0.7287 (6)0.5806 (2)0.0611 (10)
C140.0321 (4)0.8194 (5)0.6866 (2)0.0703 (11)
C30.8231 (3)0.7349 (5)0.8159 (2)0.0573 (8)
C130.0938 (4)0.8159 (6)0.7657 (2)0.0786 (12)
C180.6957 (3)0.7507 (5)0.5899 (2)0.0782 (10)
H18A0.74240.86440.61680.117*
H18B0.65170.74740.53440.117*
H18C0.76230.65430.62430.117*
C120.2296 (4)0.7648 (5)0.8371 (2)0.0762 (12)
H40.767 (2)0.664 (3)0.8631 (16)0.053 (8)*
H7A0.344 (2)0.853 (3)0.6352 (15)0.038 (7)*
H7B0.189 (2)0.902 (3)0.5479 (14)0.047 (8)*
H8A0.271 (2)0.544 (4)0.6171 (15)0.054 (9)*
H8B0.113 (2)0.601 (3)0.5336 (16)0.051 (8)*
H20.837 (3)0.797 (4)0.7435 (17)0.069 (9)*
H120.270 (3)0.764 (4)0.890 (2)0.081 (10)*
H30.915 (3)0.762 (4)0.8677 (18)0.072 (10)*
H17A0.538 (3)0.619 (4)0.5512 (17)0.065 (11)*
H140.062 (3)0.856 (4)0.6360 (18)0.071 (10)*
H50.533 (3)0.599 (4)0.7316 (17)0.078 (10)*
H130.039 (3)0.856 (4)0.7718 (18)0.085 (10)*
H110.406 (3)0.674 (4)0.883 (2)0.080 (11)*
H10.389 (2)0.513 (4)0.5800 (15)0.038 (9)*
H5A0.396 (6)0.183 (7)0.609 (4)0.20 (3)*
H17B0.518 (3)0.831 (4)0.5469 (19)0.081 (11)*
H5B0.256 (4)0.244 (6)0.535 (3)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0429 (4)0.0571 (5)0.0383 (4)0.0043 (4)0.0341 (3)0.0033 (4)
O10.0798 (13)0.0515 (14)0.0765 (13)0.0103 (11)0.0698 (12)0.0172 (11)
O20.0390 (11)0.0961 (18)0.0352 (10)0.0018 (11)0.0266 (10)0.0101 (11)
O30.0494 (12)0.0800 (17)0.0523 (12)0.0042 (11)0.0391 (11)0.0036 (11)
N10.0376 (13)0.0432 (18)0.0427 (14)0.0039 (12)0.0315 (12)0.0025 (12)
N20.0454 (13)0.0566 (17)0.0390 (13)0.0031 (11)0.0360 (12)0.0024 (11)
O40.0438 (11)0.120 (2)0.0429 (12)0.0048 (12)0.0330 (11)0.0019 (12)
O50.0721 (19)0.0574 (18)0.091 (2)0.0055 (16)0.0628 (18)0.0010 (16)
C60.0353 (14)0.0396 (17)0.0361 (15)0.0004 (12)0.0278 (13)0.0019 (13)
C70.0448 (17)0.048 (2)0.0418 (17)0.0008 (15)0.0363 (16)0.0000 (15)
C150.0474 (16)0.063 (2)0.0460 (16)0.0131 (16)0.0399 (15)0.0096 (16)
C50.0451 (17)0.048 (2)0.0450 (17)0.0046 (15)0.0367 (16)0.0051 (14)
C80.0481 (18)0.061 (2)0.0460 (18)0.0081 (18)0.0403 (17)0.0079 (17)
C100.0553 (18)0.053 (2)0.0464 (16)0.0123 (14)0.0431 (16)0.0066 (14)
C90.0460 (17)0.051 (2)0.0429 (17)0.0068 (15)0.0354 (15)0.0021 (15)
C10.0402 (15)0.050 (2)0.0472 (16)0.0015 (13)0.0362 (14)0.0019 (14)
C160.0422 (15)0.064 (2)0.0421 (16)0.0071 (16)0.0344 (15)0.0046 (17)
C40.0534 (19)0.062 (2)0.0434 (18)0.0066 (16)0.0381 (17)0.0056 (16)
C20.0455 (17)0.068 (2)0.0569 (19)0.0064 (17)0.0416 (16)0.0034 (18)
C110.070 (2)0.079 (3)0.0464 (19)0.013 (2)0.0467 (19)0.0068 (18)
C170.057 (2)0.093 (3)0.0513 (19)0.007 (2)0.0469 (18)0.004 (2)
C140.060 (2)0.107 (3)0.067 (2)0.014 (2)0.055 (2)0.015 (2)
C30.0384 (17)0.067 (2)0.0419 (18)0.0010 (17)0.0251 (16)0.0038 (17)
C130.080 (3)0.120 (4)0.076 (2)0.023 (2)0.071 (2)0.026 (2)
C180.086 (2)0.103 (3)0.092 (2)0.003 (2)0.081 (2)0.009 (2)
C120.091 (3)0.106 (3)0.060 (2)0.026 (2)0.066 (2)0.019 (2)
Geometric parameters (Å, º) top
S1—O11.4302 (19)C8—H8B0.97 (2)
S1—O21.424 (2)C10—C91.482 (4)
S1—N11.602 (3)C10—C111.369 (4)
S1—C71.777 (3)C1—C21.391 (4)
O3—C91.207 (3)C1—C171.505 (4)
N1—C61.445 (3)C4—C31.364 (4)
N1—H10.78 (3)C4—H40.93 (3)
N2—C81.459 (3)C2—C31.372 (4)
N2—C91.391 (3)C2—H20.97 (3)
N2—C161.380 (3)C11—C121.387 (5)
O4—C161.207 (3)C11—H110.96 (3)
O5—H5A0.94 (6)C17—C181.513 (4)
O5—H5B0.70 (4)C17—H17A0.95 (3)
C6—C51.376 (3)C17—H17B1.00 (3)
C6—C11.394 (3)C14—C131.375 (4)
C7—C81.512 (4)C14—H140.95 (3)
C7—H7A0.97 (2)C3—H30.93 (3)
C7—H7B0.98 (2)C13—C121.365 (5)
C15—C101.383 (4)C13—H131.01 (3)
C15—C161.474 (3)C18—H18A0.9600
C15—C141.375 (4)C18—H18B0.9600
C5—C41.375 (4)C18—H18C0.9600
C5—H50.98 (3)C12—H120.94 (3)
C8—H8A0.97 (3)
O1—S1—N1108.18 (13)C6—C1—C17120.9 (2)
O1—S1—C7106.33 (13)C2—C1—C6116.3 (2)
O2—S1—O1119.91 (12)C2—C1—C17122.8 (2)
O2—S1—N1106.50 (14)N2—C16—C15106.3 (2)
O2—S1—C7107.30 (13)O4—C16—N2124.4 (2)
N1—S1—C7108.18 (14)O4—C16—C15129.3 (3)
S1—N1—H1113.0 (19)C5—C4—H4119.9 (15)
C6—N1—S1123.1 (2)C3—C4—C5119.4 (3)
C6—N1—H1113.0 (19)C3—C4—H4120.7 (15)
C9—N2—C8123.2 (2)C1—C2—H2117.4 (16)
C16—N2—C8124.8 (2)C3—C2—C1121.9 (3)
C16—N2—C9112.0 (2)C3—C2—H2120.6 (16)
H5A—O5—H5B120 (5)C10—C11—C12117.1 (3)
C5—C6—N1119.7 (2)C10—C11—H11121.4 (19)
C5—C6—C1121.7 (2)C12—C11—H11121.5 (18)
C1—C6—N1118.6 (2)C1—C17—C18116.4 (3)
S1—C7—H7A106.2 (13)C1—C17—H17A104.8 (17)
S1—C7—H7B104.5 (13)C1—C17—H17B107.6 (17)
C8—C7—S1113.0 (2)C18—C17—H17A108.3 (17)
C8—C7—H7A113.9 (14)C18—C17—H17B110.6 (18)
C8—C7—H7B111.8 (14)H17A—C17—H17B109 (3)
H7A—C7—H7B107 (2)C15—C14—C13117.7 (4)
C10—C15—C16108.1 (2)C15—C14—H14119.3 (17)
C14—C15—C10120.7 (3)C13—C14—H14123.0 (17)
C14—C15—C16131.1 (3)C4—C3—C2120.5 (3)
C6—C5—H5118.5 (16)C4—C3—H3120.2 (18)
C4—C5—C6120.2 (3)C2—C3—H3119.3 (18)
C4—C5—H5121.3 (16)C14—C13—H13119.7 (17)
N2—C8—C7111.5 (2)C12—C13—C14121.5 (3)
N2—C8—H8A105.2 (14)C12—C13—H13118.9 (17)
N2—C8—H8B105.1 (14)C17—C18—H18A109.5
C7—C8—H8A110.1 (15)C17—C18—H18B109.5
C7—C8—H8B114.6 (15)C17—C18—H18C109.5
H8A—C8—H8B110 (2)H18A—C18—H18B109.5
C15—C10—C9107.9 (2)H18A—C18—H18C109.5
C11—C10—C15121.6 (3)H18B—C18—H18C109.5
C11—C10—C9130.4 (3)C11—C12—H12118.5 (19)
O3—C9—N2124.1 (2)C13—C12—C11121.3 (3)
O3—C9—C10130.2 (3)C13—C12—H12120.2 (19)
N2—C9—C10105.7 (2)
S1—N1—C6—C588.4 (3)C10—C15—C16—N20.7 (3)
S1—N1—C6—C193.8 (3)C10—C15—C16—O4179.1 (3)
S1—C7—C8—N2175.6 (2)C10—C15—C14—C130.4 (5)
O1—S1—N1—C647.0 (2)C10—C11—C12—C130.2 (6)
O1—S1—C7—C8177.2 (2)C9—N2—C8—C789.4 (3)
O2—S1—N1—C6177.2 (2)C9—N2—C16—O4179.1 (3)
O2—S1—C7—C847.7 (3)C9—N2—C16—C150.7 (3)
N1—S1—C7—C866.8 (3)C9—C10—C11—C12177.3 (3)
N1—C6—C5—C4178.4 (3)C1—C6—C5—C40.6 (4)
N1—C6—C1—C2178.3 (3)C1—C2—C3—C40.5 (5)
N1—C6—C1—C170.9 (4)C16—N2—C8—C792.5 (3)
C6—C5—C4—C30.1 (5)C16—N2—C9—O3179.0 (3)
C6—C1—C2—C30.0 (5)C16—N2—C9—C100.4 (3)
C6—C1—C17—C18166.9 (3)C16—C15—C10—C90.5 (3)
C7—S1—N1—C667.8 (3)C16—C15—C10—C11178.7 (3)
C15—C10—C9—O3179.4 (3)C16—C15—C14—C13177.7 (3)
C15—C10—C9—N20.1 (3)C2—C1—C17—C1812.2 (5)
C15—C10—C11—C120.5 (5)C11—C10—C9—O32.6 (5)
C15—C14—C13—C120.7 (6)C11—C10—C9—N2178.1 (3)
C5—C6—C1—C20.5 (4)C17—C1—C2—C3179.2 (3)
C5—C6—C1—C17178.6 (3)C14—C15—C10—C9178.1 (3)
C5—C4—C3—C20.4 (5)C14—C15—C10—C110.1 (5)
C8—N2—C9—O32.7 (4)C14—C15—C16—N2177.6 (3)
C8—N2—C9—C10177.9 (2)C14—C15—C16—O42.5 (6)
C8—N2—C16—O42.6 (5)C14—C13—C12—C110.3 (6)
C8—N2—C16—C15177.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O30.98 (3)2.57 (3)3.482 (3)154 (2)
N1—H1···O50.78 (3)2.00 (3)2.786 (4)176 (2)
O5—H5A···O3i0.94 (6)2.03 (6)2.862 (5)146 (5)
C17—H17B···O11.00 (3)2.55 (3)3.285 (4)130 (2)
O5—H5B···O4ii0.70 (4)2.37 (4)2.943 (4)140 (5)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y+1, z+1.
 

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