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The crystal structures of potassium [2.2]paracyclophane-4-sulfonate (1), [2.2]paracyclophane-4,15-disulfonic anhydride (2), [2.2]paracyclophane-4,15-disulfonimide (3), N-n-propyl-[2.2]paracyclophane-4,15-disulfonimide (4), N-isopropyl-[2.2]paracyclophane-4,15-disulfonimide (5), N-cyclopropyl-[2.2]paracyclophane-4,15-disulfonimide (6) and N-phenyl-[2.2]paracyclophane-4,15-disulfonimide (7) were established by single-crystal X-ray diffraction. The structural changes caused by sulfonation are discussed with respect to the parent [2.2]paracyclophane (tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene). The main features are a change in the non-bonding distances between the para-phenylene rings and a rotation of these rings with respect to the molecular symmetry plane. The rings are rotated away from each other in the case of monosulfonation (1), but are rotated in the opposite way in the case of the disulfonic anhydride (2) or the disulfonimide compounds (3)-(7). The results are also discussed in terms of the parameters proposed by Keehn [(1983), Organic Chemistry, A Series of Monographs 45, edited by P. H. Keehn & S. M. Rosenfeld, Vol. 1, pp. 69-238. New York: Academic Press] showing that (bonded and non-bonded) angles involving the para-phenylene rings are mainly affected.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101013817/an0584sup1.cif
Contains datablocks PCF1, PCF2, PCF3, PCF4, PCF5, PCF6, PCF7, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF1sup2.hkl
Contains datablock PCF1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF2sup3.hkl
Contains datablock PCF2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF3sup4.hkl
Contains datablock PCF3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF4sup5.hkl
Contains datablock PCF4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF5sup6.hkl
Contains datablock PCF5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF6sup7.hkl
Contains datablock PCF6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013817/an0584PCF7sup8.hkl
Contains datablock PCF7

CCDC references: 179352; 179353; 179354; 179355; 179356; 179357; 179358

Experimental top

PCF_1 The crystals were recrystallized from petroleum ether (60/80). A crystal was mounted into a thin-walled glass capillary under an argon atmosphere. After isotropic refinement a ΔF-synthesis revealed two peaks which were attributed to two separate water molecules.

PCF_2 After isotropic refinement a ΔF-synthesis revealed two peaks, the lowest of which at 1/2,y,1/4. These peaks were attributed to dichloromethane - one of the solvents used in the synthesis - in such a way that the C-atom of this molecule was put on the special position.

PCF_3 Absent reflections 0k0, k=2n+1 indicated space groups P21 of P21/m. Considering the value of Z, the molecular point symmetry m and the statistics of the E values, the structure was refined in P21/m. After isotropic refinement a ΔF-synthesis revealed six peaks, which are all at y=1/4. These peaks were attributed to two molecules of methylcyanide, one of the solvents used in the synthesis. Hydrogen atoms were introduced as riding atoms, with a fixed isotropic displacement parameter

PCF_4 The crystals are of poor quality. Hydrogen atoms were introduced as riding atoms, with a fixed isotropic displacement parameter

Computing details top

For all compounds, data collection: Enraf-Nonius CAD-4 Software; cell refinement: CELCON prog. comparable to xtal_LATCON. Data reduction: xtal_SORTRF (Hall, Spadaccini & Stewart, 1992) for PCF1; xtal_ADDREF (Davenport & Hall, 1992) for PCF2, PCF6; xtal_ADDREF (Davenport & Hall, 1992)_SORTRF (Hall, Spadaccini & Stewart, 1992) for PCF3, PCF7; Xtal for PCF4; xtal_ADDREF (Davenport & Hall, 1992)_SORTRF_(Hall, Spadaccini & Stewart, 1992) for PCF5. For all compounds, program(s) used to solve structure: xtal_SIMPEL (Schenk & Hall, 1992); program(s) used to refine structure: xtal_CRYLSQ (Olthof-Hazekamp, 1992); molecular graphics: xtal_ORTEP (Davenport, Hall & Dreissig, 1992); software used to prepare material for publication: xtal_BONDLA_(Dreissig, Doherty, Stewart & Hall, 1992)_CIFIO_(Hall, 1992).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(PCF1) potassium [2.2]paracyclophane-4-sulfonate top
Crystal data top
C16H15SO3+K.2H2OF(000) = 760
Mr = 362.5Dx = 1.50 Mg m3
Monoclinic, P21/aCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yabCell parameters from 23 reflections
a = 11.493 (3) Åθ = 39.9–42.8°
b = 7.685 (1) ŵ = 4.34 mm1
c = 18.150 (3) ÅT = 213 K
β = 91.49 (2)°Rod, colourless
V = 1602.5 (5) Å31.25 × 0.70 × 0.20 mm
Z = 4
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 64.9°, θmin = 4.9°
Graphite monochromatorh = 013
θ/2θ scansk = 09
2709 measured reflectionsl = 2121
2709 independent reflections2 standard reflections every 60 min
2633 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullRiding
R[F2 > 2σ(F2)] = 0.086 1/[5.9 + 0.0038*σ(Fobs)2 + 0.00002/σ(Fobs)]
wR(F2) = 0.087(Δ/σ)max = 0.09
S = 1.36Δρmax = 1.06 e Å3
2633 reflectionsΔρmin = 0.66 e Å3
269 parametersExtinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
19 restraintsExtinction coefficient: 264 (75)
Crystal data top
C16H15SO3+K.2H2OV = 1602.5 (5) Å3
Mr = 362.5Z = 4
Monoclinic, P21/aCu Kα radiation
a = 11.493 (3) ŵ = 4.34 mm1
b = 7.685 (1) ÅT = 213 K
c = 18.150 (3) Å1.25 × 0.70 × 0.20 mm
β = 91.49 (2)°
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
2709 measured reflections2 standard reflections every 60 min
2709 independent reflections intensity decay: none
2633 reflections with refl observed if I > 2.5 σ(I )
Refinement top
R[F2 > 2σ(F2)] = 0.08619 restraints
wR(F2) = 0.087Riding
S = 1.36Δρmax = 1.06 e Å3
2633 reflectionsΔρmin = 0.66 e Å3
269 parameters
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0556 (5)0.8953 (9)0.6988 (3)0.038 (3)
C20.1719 (5)0.8550 (8)0.7365 (3)0.033 (3)
C30.2766 (5)0.9362 (7)0.7207 (3)0.030 (3)
C40.3635 (5)0.9574 (8)0.7748 (3)0.031 (3)
C50.3496 (5)0.8887 (8)0.8454 (3)0.037 (3)
C60.2598 (6)0.7689 (8)0.8536 (3)0.040 (3)
C70.1725 (5)0.7544 (8)0.8002 (4)0.037 (3)
C80.4129 (6)0.965 (1)0.9122 (4)0.046 (4)
C90.0114 (6)1.047 (1)0.7376 (4)0.053 (4)
C100.0497 (5)1.1166 (9)0.8061 (4)0.042 (4)
C110.1409 (6)1.2360 (8)0.7996 (4)0.041 (4)
C120.2270 (5)1.2486 (9)0.8543 (4)0.041 (3)
C130.2249 (6)1.1431 (9)0.9167 (3)0.041 (3)
C140.1213 (6)1.0565 (9)0.9298 (4)0.042 (4)
C150.0353 (6)1.0427 (9)0.8756 (4)0.042 (4)
C160.3362 (6)1.093 (1)0.9574 (4)0.051 (4)
O10.4241 (4)1.0717 (6)0.6314 (2)0.042 (2)
O20.2729 (4)0.8886 (6)0.5803 (2)0.045 (3)
O30.2280 (4)1.1776 (6)0.6222 (2)0.046 (3)
S0.3015 (1)1.0278 (2)0.63207 (7)0.0310 (7)
K0.4391 (1)0.7674 (2)0.48204 (8)0.0394 (8)
O1s0.3747 (4)0.4534 (6)0.5453 (2)0.044 (3)
O2s0.6165 (4)0.9073 (6)0.5721 (2)0.046 (3)
H1010.005 (5)0.790 (5)0.694 (4)0.05 (2)*
H1020.060 (5)0.942 (7)0.648 (1)0.04 (2)*
H40.431 (3)1.035 (6)0.764 (3)0.02 (1)*
H60.256 (4)0.707 (6)0.902 (2)0.02 (1)*
H70.106 (4)0.673 (7)0.807 (3)0.05 (2)*
H810.436 (5)0.873 (6)0.949 (2)0.03 (2)*
H820.488 (4)1.02 (1)0.900 (4)0.08 (3)*
H910.021 (7)1.143 (7)0.701 (3)0.08 (3)*
H920.093 (3)1.009 (9)0.747 (4)0.06 (2)*
H110.151 (5)1.299 (7)0.752 (2)0.03 (2)*
H120.295 (4)1.326 (7)0.847 (4)0.05 (2)*
H140.117 (5)0.994 (6)0.978 (2)0.02 (1)*
H150.036 (3)0.977 (7)0.889 (3)0.05 (2)*
H1610.325 (5)1.036 (7)1.006 (2)0.04 (2)*
H1620.379 (6)1.197 (6)0.977 (4)0.06 (2)*
H11s0.353260.395020.592280.08000*
H12s0.330340.379020.511390.08000*
H21s0.580840.982460.608180.15000*
H22s0.683280.880270.605270.08000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.033 (3)0.043 (4)0.036 (3)0.008 (3)0.001 (3)0.001 (3)
C20.036 (3)0.031 (3)0.034 (3)0.001 (3)0.005 (2)0.009 (3)
C30.037 (3)0.027 (3)0.025 (3)0.002 (2)0.007 (2)0.001 (2)
C40.031 (3)0.029 (3)0.033 (3)0.001 (2)0.003 (2)0.000 (2)
C50.032 (3)0.039 (3)0.041 (3)0.011 (3)0.003 (3)0.001 (3)
C60.048 (4)0.037 (4)0.035 (3)0.010 (3)0.010 (3)0.011 (3)
C70.039 (3)0.030 (3)0.044 (4)0.004 (3)0.011 (3)0.001 (3)
C80.045 (4)0.058 (5)0.034 (3)0.005 (3)0.004 (3)0.002 (3)
C90.041 (4)0.065 (5)0.053 (4)0.010 (4)0.012 (3)0.006 (4)
C100.033 (3)0.041 (4)0.052 (4)0.012 (3)0.006 (3)0.005 (3)
C110.047 (4)0.034 (3)0.043 (4)0.014 (3)0.010 (3)0.005 (3)
C120.037 (3)0.035 (3)0.050 (4)0.003 (3)0.011 (3)0.007 (3)
C130.042 (4)0.043 (4)0.037 (3)0.005 (3)0.004 (3)0.015 (3)
C140.050 (4)0.038 (4)0.039 (3)0.007 (3)0.011 (3)0.001 (3)
C150.037 (3)0.036 (4)0.052 (4)0.001 (3)0.010 (3)0.002 (3)
C160.053 (4)0.059 (5)0.040 (4)0.007 (4)0.004 (3)0.012 (4)
O10.039 (2)0.048 (3)0.040 (2)0.000 (2)0.008 (2)0.008 (2)
O20.050 (3)0.052 (3)0.032 (2)0.007 (2)0.005 (2)0.001 (2)
O30.049 (3)0.050 (3)0.039 (2)0.004 (2)0.002 (2)0.009 (2)
S0.0327 (7)0.0332 (8)0.0273 (7)0.0016 (6)0.0018 (5)0.0023 (6)
K0.0354 (7)0.0352 (8)0.0476 (8)0.0012 (6)0.0012 (6)0.0035 (6)
O1s0.041 (2)0.039 (3)0.053 (3)0.002 (2)0.001 (2)0.009 (2)
O2s0.049 (3)0.043 (3)0.047 (3)0.006 (2)0.006 (2)0.005 (2)
Geometric parameters (Å, º) top
C1—H1011.00 (5)C10—C111.400 (9)
C1—H1021.00 (3)C11—H111.00 (4)
C1—C21.517 (8)C11—C121.387 (9)
C1—C91.57 (1)C12—H121.00 (5)
C2—C71.390 (9)C12—C131.394 (9)
C2—C31.392 (8)C13—C141.390 (9)
C3—C41.393 (8)C13—C161.51 (1)
C3—S1.786 (6)C14—H141.00 (3)
C4—H41.00 (4)C14—C151.381 (9)
C4—C51.399 (8)C15—H151.00 (5)
C5—C61.394 (9)C16—H1621.00 (5)
C5—C81.514 (9)C16—H1611.00 (4)
C6—H61.00 (3)O1—S1.449 (4)
C6—C71.382 (9)O2—S1.455 (5)
C7—H71.00 (5)O2—K2.806 (5)
C8—H821.00 (5)O3—S1.437 (5)
C8—H811.00 (4)K—O1s2.781 (4)
C8—C161.57 (1)K—O2s2.795 (4)
C9—H911.00 (6)O1s—H12s0.974 (4)
C9—H921.00 (4)O1s—H11s0.999 (4)
C9—C101.51 (1)O2s—H21s0.971 (4)
C10—C151.40 (1)O2s—H22s0.984 (4)
H21s···H22s1.4174 (3)O1s···O1sx3.430 (6)
H11s···H12s1.4899 (2)K···H102xiv3.43 (5)
H161···H1621.49 (8)C12···H92vi3.43 (6)
H81···H821.57 (9)C3···C93.439 (9)
H91···H921.57 (9)H91···H12vii3.44 (9)
H101···H1021.58 (7)S···H22siv3.447 (1)
O1···H21s1.984 (4)C8···C143.45 (1)
C9···H1022.02 (4)O3···H22svii3.449 (5)
O2···H12si2.021 (4)O2···O2sxiii3.452 (6)
C13···H142.04 (5)S···H91vi3.46 (7)
C14···H152.04 (4)C3···C123.470 (9)
C2···H72.05 (6)O3···H91vi3.47 (7)
C5···H62.05 (5)C14···H15viii3.47 (6)
C16···H812.05 (5)C10···H73.47 (5)
H102···H912.06 (8)C8···H15ix3.47 (6)
C10···H912.06 (6)H102···H113.48 (7)
C12···H112.07 (4)H101···H11siv3.48 (5)
C3···H42.07 (4)C12···H15vi3.48 (5)
C13···H122.07 (6)C14···H162vii3.49 (6)
C11···H122.07 (5)C4···C163.496 (9)
C6···H72.07 (5)S···H12sii3.497 (1)
C8···H1612.08 (4)O1s···O2sx3.500 (6)
C10···H112.08 (5)H7···H12xii3.50 (7)
C5···H42.09 (5)S···H113.50 (5)
C7···H62.09 (3)O1···H11vi3.51 (5)
H81···H1612.09 (7)C6···H1613.51 (4)
C15···H142.09 (4)H161···H162iii3.52 (8)
C13···H1622.10 (6)C14···H6xi3.53 (4)
C1···H912.10 (6)C7···H92ix3.53 (5)
C5···H812.10 (5)C7···H82iv3.53 (7)
C10···H922.11 (5)H4···H92vi3.53 (8)
C2···H1012.11 (6)H81···H14ix3.54 (7)
C10···H152.11 (6)H6···H82iv3.54 (7)
C5···H822.11 (6)S···H101ix3.55 (5)
C1···H922.12 (5)H91···H21svii3.55 (6)
C13···H1612.13 (4)O3···O2svii3.547 (6)
C16···H822.13 (6)C6···H162iii3.55 (7)
C9···H1012.14 (5)C12···H823.55 (5)
C2···H1022.14 (4)H12···H14xi3.55 (7)
C8···H1622.18 (5)H12s···H21siv3.5643 (6)
H101···H922.25 (8)H4···H813.57 (7)
O3···H11sii2.280 (5)C4···O33.569 (7)
H82···H1622.33 (9)C8···H82v3.57 (7)
H6···H161iii2.34 (6)C9···O1vii3.573 (9)
C3···C72.356 (8)C13···H81xi3.57 (5)
O2···H22siv2.358 (5)H92···H113.58 (7)
H14···H152.37 (7)H102···H73.58 (7)
H11···H122.37 (7)O1···K3.588 (5)
C12···C142.371 (9)H82···H11vi3.59 (8)
C4···C62.377 (9)H14···H161iii3.59 (7)
C11···C152.380 (9)C5···H101ix3.60 (6)
O1···O32.397 (6)C4···H113.60 (5)
O1···O22.402 (6)O2···H101ix3.60 (6)
C5···C72.408 (9)H7···H923.60 (8)
O2···O32.408 (7)O1s···H102xiv3.60 (3)
C13···C152.412 (9)C7···H4iv3.60 (4)
C10···C142.417 (9)H6···H823.60 (8)
H6···H72.42 (7)K···H91xiv3.60 (6)
C11···C132.419 (9)O2···O1s3.605 (6)
C10···C122.420 (9)O3···H43.60 (4)
C2···C62.421 (8)C5···H92ix3.61 (7)
C3···C52.422 (8)C4···H91vi3.61 (6)
C2···C42.423 (8)C7···H11xii3.62 (5)
H14···H162iii2.42 (7)C14···H82vii3.62 (7)
O1···H42.43 (5)C2···H21siv3.622 (6)
H91···H11siv2.43 (7)H14···H162vii3.62 (8)
H14···H1612.44 (8)C1···O1siv3.625 (7)
H91···H112.47 (9)H7···H161iii3.62 (7)
C1···C72.496 (9)O1s···H21siv3.626 (4)
H101···H72.50 (8)O1s···H101ix3.63 (6)
C9···C112.52 (1)O2···H21s3.634 (4)
C14···C162.52 (1)C8···H143.64 (5)
C12···C162.53 (1)C12···H6ii3.64 (5)
H4···H822.53 (9)C12···H7ii3.64 (5)
C6···C82.53 (1)C9···O33.641 (9)
C4···C82.543 (9)C15···H63.64 (5)
H81···H162v2.55 (8)K···H11s3.643 (1)
C9···C152.55 (1)C2···O2siv3.643 (7)
H12···H15vi2.55 (7)K···H22s3.647 (1)
C8···C132.56 (1)O2···H21siv3.650 (5)
H6···H812.57 (7)K···H102ix3.65 (4)
C3···O22.573 (7)C15···H81iv3.66 (5)
C2···C92.57 (1)C4···H92ix3.66 (7)
C5···C162.58 (1)O3···O1si3.664 (6)
C1···C32.579 (8)C11···H1023.67 (4)
C1···C102.587 (9)C5···C113.669 (9)
H92···H12vii2.59 (9)C7···H12xii3.67 (5)
C3···O12.594 (7)O1s···H92ix3.68 (7)
O1···H91vi2.60 (6)C1···H153.68 (6)
H102···H922.60 (7)C6···C103.688 (9)
H11s···H22siv2.6226 (4)C7···H22siv3.691 (6)
C3···O32.626 (7)C4···O23.692 (7)
H81···H1622.63 (7)C9···O1siv3.696 (9)
H14···H15viii2.63 (7)C7···C133.700 (9)
C11···H912.64 (7)C14···H73.70 (6)
H92···H152.65 (9)C6···C123.706 (9)
C1···H72.65 (6)C8···C16v3.71 (1)
H7···H82iv2.66 (9)O1···O2sxiii3.715 (6)
C16···H142.66 (5)C7···C113.718 (9)
H4···H7ix2.67 (6)K···H11si3.720 (2)
C8···H62.68 (5)C16···H43.72 (5)
C14···H1612.69 (5)C5···H143.73 (4)
O3···H1022.69 (6)C7···H923.73 (5)
C4···H822.70 (7)C4···H73.74 (5)
C9···H112.70 (6)S···O1sii3.736 (4)
O3···H112.70 (4)C7···H43.74 (4)
O1···H11sii2.704 (5)C1···C63.741 (9)
C7···H1012.70 (6)C12···H153.74 (5)
H12···H1622.70 (9)C3···H63.74 (3)
C16···H122.72 (6)C15···H123.74 (5)
C4···S2.724 (6)C11···H43.74 (4)
H82···H1612.73 (8)C11···H143.75 (4)
H6···H162iii2.73 (8)C13···H14xi3.75 (5)
H101···H912.74 (7)C2···C123.748 (9)
C4···C72.742 (8)C15···C163.75 (1)
C15···H922.74 (6)C14···H113.75 (4)
C3···C62.744 (8)C9···C123.75 (1)
C8···H42.75 (5)C7···C83.754 (9)
C12···C152.748 (9)C11···C163.76 (1)
O2s···H12sx2.750 (4)C13···H82vii3.76 (6)
C11···C142.750 (9)C8···C8v3.759 (9)
C6···H812.75 (5)C3···H92ix3.76 (7)
H82···H161v2.75 (8)S···K3.761 (2)
H101···H21siv2.76 (5)C9···C143.77 (1)
C5···C132.765 (9)C13···H43.78 (5)
C2···C102.775 (9)C15···H6iv3.78 (5)
C2···S2.779 (6)C3···H123.78 (6)
O1···O2s2.788 (6)C3···H913.78 (8)
H6···H15ix2.79 (7)C1···C4iv3.780 (9)
C3···H1022.79 (5)C11···H92vi3.78 (5)
O1s···H22siv2.789 (4)C7···H143.78 (4)
H4···H91vi2.79 (7)C3···C83.781 (8)
O2···H1022.79 (5)C1···C43.794 (8)
S···H42.79 (5)O1s···H12sx3.794 (4)
C10···C132.814 (9)O1s···H22sx3.794 (4)
C9···H152.81 (6)S···O1si3.802 (4)
C2···C52.817 (8)O2s···H11sx3.805 (4)
C12···H1622.82 (7)C1···H4iv3.81 (4)
O3···H12sii2.820 (4)C2···H153.82 (5)
H14···H14viii2.84 (7)O2···H1013.82 (6)
H102···H11siv2.85 (6)C6···H153.83 (4)
C4···O12.851 (7)C4···H11vi3.83 (6)
O2···O1si2.851 (6)C16···H15vi3.83 (6)
H4···H11vi2.85 (7)C15···H1013.84 (6)
S···H1022.87 (6)O1···H92vi3.85 (7)
K···H12sx2.878 (1)O2···H22sxiii3.853 (4)
O2···O2siv2.900 (6)C5···C153.854 (9)
O1s···H102ix2.90 (5)O3···H92vi3.86 (6)
H12s···H22sx2.9088 (3)C4···C103.864 (8)
C16···H6xi2.93 (4)C6···C16iii3.87 (1)
H81···H15ix2.93 (7)S···Ki3.877 (2)
C4···H101ix2.93 (5)C15···H162iii3.88 (6)
H81···H161v2.93 (8)S···O2sxiii3.880 (4)
H101···H22siv2.94 (6)C2···O13.886 (7)
H101···H4iv2.95 (6)C14···H813.89 (5)
H92···H11siv2.95 (7)C2···H92ix3.89 (6)
H102···H22siv2.97 (6)C2···C143.893 (9)
C15···H12vii2.97 (5)C7···H161iii3.90 (4)
H81···H82v2.97 (9)K···O1si3.899 (4)
S···H11sii2.977 (1)C12···C15vi3.899 (9)
O2s···H101ix2.99 (6)O2···H11s3.909 (5)
C2···H22siv2.996 (6)K···H22siv3.909 (1)
C4···H7ix3.01 (5)C14···H161xi3.91 (5)
K···H11sx3.040 (1)C5···C103.915 (9)
H81···H81v3.04 (7)S···O2s3.919 (5)
C11···H4vii3.04 (4)K···H101ix3.92 (6)
H12s···H22siv3.0548 (3)C14···C14viii3.922 (9)
C9···H11siv3.060 (7)C4···C7ix3.923 (8)
C7···C153.063 (9)O2···H43.93 (5)
C6···H15ix3.06 (5)C15···C16vii3.93 (1)
O3···O1sii3.067 (6)C16···H161xi3.93 (6)
H6···H14iii3.07 (6)C11···S3.938 (7)
C10···H12vii3.07 (5)O2···Ki3.944 (5)
H6···H143.07 (7)C4···C10vi3.944 (9)
C6···C143.074 (9)C6···H82iv3.95 (6)
C5···H7ix3.09 (5)C14···H81iv3.95 (5)
H7···H11xii3.09 (7)C6···H14iii3.95 (4)
O2s···H102ix3.09 (5)C6···C113.955 (9)
C16···H81v3.09 (5)C3···C133.955 (8)
C10···H4vii3.09 (4)O2···O2s3.958 (6)
C2···O23.102 (7)O2s···O2sxiii3.962 (6)
C1···H22siv3.107 (6)C7···C123.968 (9)
C4···C123.109 (9)C12···H14xi3.97 (4)
C5···C123.110 (9)C10···C12vii3.970 (9)
O3···H21svii3.119 (5)C5···C15ix3.973 (9)
H6···H12xii3.12 (7)C10···H162vii3.98 (7)
C7···C103.124 (9)O2···H21sxiii3.977 (4)
C6···C133.125 (9)C5···C7ix3.977 (9)
O2s···H11six3.129 (4)C4···H21s3.977 (6)
O1s···H91ix3.13 (6)C4···C11vi3.980 (9)
O1···H101ix3.13 (5)C6···C15ix3.982 (9)
H4···H123.14 (7)O2s···H11vi3.98 (4)
H15···H162vii3.14 (8)C2···C133.983 (9)
C5···H1613.15 (4)C10···O33.989 (8)
C3···C113.148 (9)C15···H4vii3.99 (4)
C14···H63.15 (5)O1···O3vi3.996 (6)
C8···H7ix3.15 (5)S···Kxiii3.997 (2)
H82···H162v3.17 (9)C7···H81iv4.00 (5)
C11···H82vii3.17 (7)C7···C11xii4.001 (9)
C2···C113.167 (9)C3···H91vi4.00 (7)
C9···H12vii3.18 (6)O2···H11sii4.004 (5)
O2s···H12six3.177 (4)C12···H914.01 (7)
C10···H1023.18 (3)C6···C12xii4.016 (9)
C13···H823.19 (5)O2···O3xiv4.018 (6)
C2···H913.19 (7)C7···S4.019 (7)
S···H12si3.190 (1)C7···C8iv4.024 (9)
C5···H15ix3.19 (6)C15···H1614.03 (5)
H11···H21svii3.19 (4)C9···C12vii4.04 (1)
C3···H113.19 (5)S···H914.04 (8)
C3···H101ix3.20 (5)C5···S4.041 (6)
O1s···O2siv3.203 (6)S···H1014.04 (5)
C8···C123.21 (1)O3···O2sxiii4.049 (6)
H102···H12si3.21 (3)C7···C12xii4.055 (9)
K···H12si3.219 (2)C1···O1iv4.071 (8)
C15···H73.22 (5)C8···C11vi4.07 (1)
K···H21s3.230 (1)C14···C15viii4.077 (9)
C4···H123.23 (6)C4···C144.080 (9)
C6···C163.23 (1)C3···C154.083 (9)
C13···H813.23 (5)C8···C10vi4.08 (1)
C15···H14viii3.24 (4)S···O2siv4.094 (5)
H7···H153.24 (8)C8···C15vi4.10 (1)
C14···H162iii3.24 (5)C9···S4.120 (8)
O3···H913.24 (8)C1···C3iv4.124 (9)
C3···H73.25 (5)C14···C16iii4.13 (1)
C14···H1623.25 (6)C4···C9vi4.13 (1)
H6···H1613.25 (6)C11···O1vii4.162 (8)
C12···H143.25 (4)C3···O2siv4.167 (7)
C16···H63.27 (5)C9···O3vii4.184 (9)
C1···S3.266 (6)C6···C9ix4.19 (1)
C10···H1013.27 (5)C4···C9ix4.20 (1)
C8···H81v3.27 (5)C10···O1vii4.199 (8)
C4···H63.27 (4)C8···C15ix4.21 (1)
S···H21s3.270 (2)C5···C9ix4.22 (1)
C14···H123.27 (5)C13···C16xi4.22 (1)
C7···C93.27 (1)C1···C5iv4.217 (9)
H81···H14iii3.27 (6)C10···C164.24 (1)
C1···O33.272 (8)C8···C114.24 (1)
C2···H923.27 (4)C5···O14.239 (7)
C14···H14viii3.27 (5)C9···C134.25 (1)
C15···H162vii3.28 (6)C1···C54.246 (8)
C6···H161iii3.28 (4)C12···O34.247 (8)
K···H12s3.285 (1)C2···C84.253 (9)
C6···H43.29 (4)C7···C164.27 (1)
H11s···H21siv3.2893 (8)C8···C14iii4.28 (1)
C13···H153.29 (4)C14···C16vii4.28 (1)
C15···H113.29 (5)C6···C13iii4.279 (9)
H7···H81iv3.29 (8)C16···C16v4.28 (1)
C8···H123.29 (6)S···H92vi4.28 (7)
H92···H11vii3.30 (7)C4···C154.285 (9)
C11···H153.30 (5)C6···C94.29 (1)
C2···O33.307 (7)C8···C13iii4.30 (1)
C2···H43.31 (4)K···O2siv4.306 (5)
C4···H813.31 (5)C7···O24.307 (8)
C13···H113.31 (4)C1···Kiv4.309 (6)
C6···H143.31 (4)C9···Svii4.330 (8)
C15···H913.31 (6)O3···Kxiii4.333 (5)
C5···H73.31 (5)C3···C144.336 (9)
C10···H123.32 (5)C10···C16vii4.35 (1)
C9···H4vii3.32 (4)C1···C124.350 (9)
C11···H923.32 (5)C2···C4iv4.352 (8)
C12···H43.32 (4)C7···O2siv4.353 (8)
C1···C113.326 (9)K···H11xiv4.35 (3)
C2···H63.33 (3)C1···Ki4.355 (7)
C8···H161v3.33 (5)O2···Kiv4.357 (5)
C10···H143.33 (3)O3···O1siv4.377 (6)
C8···H162v3.33 (6)C8···C12vi4.38 (1)
C5···C143.332 (9)K···Kx4.385 (2)
C16···H14xi3.33 (5)C13···C15vi4.387 (9)
C13···H6xi3.33 (3)C10···S4.392 (7)
C2···C153.336 (9)C8···C14vi4.40 (1)
C3···H1013.34 (5)C4···C94.398 (9)
C1···O23.338 (8)C12···C16xi4.40 (1)
C10···H82vii3.34 (8)O2···Kxiii4.406 (5)
H82···H123.35 (8)C8···C154.413 (9)
C7···H1023.35 (4)C1···C144.418 (9)
C6···H823.35 (6)C6···C11xii4.420 (9)
H102···H21siv3.35 (6)C9···Ki4.429 (8)
C1···H21siv3.354 (7)C6···C14iii4.439 (9)
C1···O2siv3.357 (8)C12···S4.479 (7)
C6···C153.361 (9)C1···Siv4.516 (7)
C14···H81xi3.36 (4)C6···S4.522 (6)
C16···H82v3.36 (7)O3···K4.756 (5)
O1···O1sii3.365 (6)O1···Ki4.845 (4)
C3···C103.366 (9)K···H12sii4.896 (1)
C3···H22siv3.367 (5)K···H101xiv4.91 (5)
O1···H22s3.367 (4)C3···K4.935 (6)
C7···C143.368 (9)K···H92xiv4.97 (7)
C12···H1613.37 (4)K···H4xiii4.99 (5)
C6···H92ix3.37 (6)C3···Ki5.068 (6)
O1···H12sii3.370 (4)K···H91ix5.09 (6)
C5···H1623.37 (6)K···H21siv5.136 (2)
C4···C113.375 (9)C11···Ki5.176 (7)
C4···C133.379 (9)K···H101i5.18 (5)
H4···H21s3.38 (5)C2···Ki5.210 (6)
C11···H7ii3.38 (5)C9···Kiv5.249 (8)
C13···H161xi3.38 (5)K···H12six5.269 (2)
C13···H63.39 (5)K···H92ix5.27 (7)
C7···H153.39 (5)K···O2sx5.313 (5)
C12···H82vii3.39 (6)C2···Kiv5.360 (6)
H14···H1623.39 (8)C10···Ki5.361 (7)
C1···H11siv3.393 (6)O3···Kiv5.362 (5)
O3···H12si3.393 (5)S···Kiv5.414 (2)
C9···H73.41 (5)K···O1sii5.450 (5)
C1···C153.416 (9)O2···Kxiv5.465 (5)
O2···H11si3.419 (4)C3···Kxiii5.480 (6)
C1···H113.42 (5)K···O1six5.539 (4)
C5···H123.42 (6)C4···K5.601 (6)
K···H22sxiii3.421 (1)C4···Kxiii5.649 (6)
C15···H82vii3.42 (8)C2···K5.653 (6)
C12···H161xi3.43 (4)K···Kix5.753 (2)
C11···O33.426 (8)K···Kiv5.753 (2)
C6···H12xii3.43 (6)K···Ki5.851 (2)
C2···H113.43 (5)K···Kxiv5.851 (2)
H12···H161xi3.43 (8)
H101—C1—H102104 (5)C11—C10—C9119.7 (6)
H101—C1—C2112 (3)H11—C11—C12119 (3)
H101—C1—C9111 (3)H11—C11—C10120 (3)
H102—C1—C2115 (3)C12—C11—C10120.5 (6)
H102—C1—C9101 (3)H12—C12—C11120 (4)
C2—C1—C9112.7 (5)H12—C12—C13119 (4)
C7—C2—C3115.8 (5)C11—C12—C13120.9 (6)
C7—C2—C1118.3 (5)C14—C13—C12116.8 (6)
C3—C2—C1124.8 (5)C14—C13—C16120.9 (6)
C2—C3—C4121.0 (5)C12—C13—C16120.8 (6)
C2—C3—S121.5 (4)H14—C14—C15123 (3)
C4—C3—S117.4 (4)H14—C14—C13116 (3)
H4—C4—C3119 (3)C15—C14—C13121.0 (6)
H4—C4—C5120 (3)H15—C15—C14117 (3)
C3—C4—C5120.4 (5)H15—C15—C10122 (3)
C6—C5—C4116.7 (5)C14—C15—C10120.9 (6)
C6—C5—C8120.8 (6)H162—C16—H16197 (5)
C4—C5—C8121.6 (6)H162—C16—C13112 (3)
H6—C6—C7122 (3)H162—C16—C8114 (4)
H6—C6—C5117 (3)H161—C16—C13114 (3)
C7—C6—C5120.3 (6)H161—C16—C8106 (3)
H7—C7—C6121 (3)C13—C16—C8112.5 (6)
H7—C7—C2118 (3)S—O2—K120.6 (2)
C6—C7—C2121.8 (6)O3—S—O1112.4 (3)
H82—C8—H81104 (5)O3—S—O2112.8 (3)
H82—C8—C5113 (4)O3—S—C3108.7 (3)
H82—C8—C16110 (4)O1—S—O2111.7 (3)
H81—C8—C5112 (3)O1—S—C3106.2 (3)
H81—C8—C16104 (3)O2—S—C3104.6 (3)
C5—C8—C16113.4 (6)O1s—K—O2s106.9 (1)
H91—C9—H92104 (6)O1s—K—O280.3 (1)
H91—C9—C10109 (4)O2s—K—O289.9 (1)
H91—C9—C1107 (4)H12s—O1s—H11s98.0 (4)
H92—C9—C10113 (4)H12s—O1s—K112.9 (3)
H92—C9—C1109 (4)H11s—O1s—K144.7 (3)
C10—C9—C1114.1 (6)H21s—O2s—H22s92.9 (4)
C15—C10—C11116.6 (6)H21s—O2s—K108.0 (3)
C15—C10—C9122.5 (6)H22s—O2s—K145.2 (3)
C9—C1—C2—C388.1 (7)H81—C8—C16—H1618 (5)
C9—C1—C2—C779.4 (7)H81—C8—C16—H16297 (5)
H101—C1—C2—C3146 (4)H82—C8—C16—C13116 (4)
H101—C1—C2—C747 (4)H82—C8—C16—H161119 (6)
H102—C1—C2—C327 (4)H82—C8—C16—H16213 (6)
H102—C1—C2—C7166 (3)C1—C9—C10—C1180.6 (8)
C2—C1—C9—C102.8 (8)C1—C9—C10—C1586.6 (8)
C2—C1—C9—H91118 (5)H91—C9—C10—C1139 (5)
C2—C1—C9—H92130 (4)H91—C9—C10—C15153 (5)
H101—C1—C9—C10124 (4)H92—C9—C10—C11154 (4)
H101—C1—C9—H91115 (6)H92—C9—C10—C1538 (4)
H101—C1—C9—H923 (6)C9—C10—C11—C12153.7 (7)
H102—C1—C9—C10126 (3)C9—C10—C11—H1116 (4)
H102—C1—C9—H915 (6)C15—C10—C11—C1214.3 (9)
H102—C1—C9—H92107 (5)C15—C10—C11—H11176 (4)
C1—C2—C3—C4149.7 (6)C9—C10—C15—C14153.5 (7)
C1—C2—C3—S26.8 (8)C9—C10—C15—H1526 (4)
C7—C2—C3—C418.1 (8)C11—C10—C15—C1414 (1)
C7—C2—C3—S165.4 (5)C11—C10—C15—H15166 (4)
C1—C2—C7—C6152.7 (6)C10—C11—C12—C130 (1)
C1—C2—C7—H726 (4)C10—C11—C12—H12175 (4)
C3—C2—C7—C615.9 (9)H11—C11—C12—C13170 (3)
C3—C2—C7—H7166 (3)H11—C11—C12—H124 (5)
C2—C3—C4—C53.5 (9)C11—C12—C13—C1415 (1)
C2—C3—C4—H4169 (3)C11—C12—C13—C16151.8 (7)
S—C3—C4—C5179.9 (5)H12—C12—C13—C14171 (4)
S—C3—C4—H48 (3)H12—C12—C13—C1623 (4)
C2—C3—S—O1170.0 (5)C12—C13—C14—C1515 (1)
C2—C3—S—O251.8 (5)C12—C13—C14—H14172 (3)
C2—C3—S—O368.9 (5)C16—C13—C14—C15151.6 (7)
C4—C3—S—O113.4 (5)C16—C13—C14—H1421 (3)
C4—C3—S—O2131.6 (5)C12—C13—C16—C869.6 (9)
C4—C3—S—O3107.7 (5)C12—C13—C16—H161170 (3)
C3—C4—C5—C613.7 (9)C12—C13—C16—H16261 (4)
C3—C4—C5—C8154.9 (6)C14—C13—C16—C896.2 (8)
H4—C4—C5—C6174 (3)C14—C13—C16—H16125 (3)
H4—C4—C5—C817 (3)C14—C13—C16—H162133 (4)
C4—C5—C6—C716.1 (9)C13—C14—C15—C100 (1)
C4—C5—C6—H6172 (3)C13—C14—C15—H15179 (4)
C8—C5—C6—C7152.7 (6)H14—C14—C15—C10173 (3)
C8—C5—C6—H620 (3)H14—C14—C15—H157 (5)
C4—C5—C8—C1698.3 (7)K—O2—S—C3122.0 (3)
C4—C5—C8—H81144 (3)K—O2—S—O17.6 (3)
C4—C5—C8—H8228 (4)K—O2—S—O3120.1 (3)
C6—C5—C8—C1670.0 (8)S—O2—K—O1s127.3 (3)
C6—C5—C8—H8147 (3)S—O2—K—O2s20.2 (3)
C6—C5—C8—H82164 (4)O2—K—O1s—H11s39.0 (5)
C5—C6—C7—C21 (1)O2—K—O1s—H12s109.9 (3)
C5—C6—C7—H7177 (4)O2s—K—O1s—H11s47.9 (6)
H6—C6—C7—C2173 (3)O2s—K—O1s—H12s163.2 (3)
H6—C6—C7—H75 (5)O2—K—O2s—H21s11.8 (3)
C5—C8—C16—C1311.9 (9)O2—K—O2s—H22s112.2 (6)
C5—C8—C16—H161114 (3)O1s—K—O2s—H21s91.7 (3)
C5—C8—C16—H162141 (4)O1s—K—O2s—H22s32.3 (6)
H81—C8—C16—C13134 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x, y+1, z; (iii) x+1/2, y1/2, z+2; (iv) x1/2, y+3/2, z; (v) x+1, y+2, z+2; (vi) x+1/2, y+5/2, z; (vii) x1/2, y+5/2, z; (viii) x, y+2, z+2; (ix) x+1/2, y+3/2, z; (x) x+1, y+1, z+1; (xi) x+1/2, y+1/2, z+2; (xii) x, y1, z; (xiii) x+1, y+2, z+1; (xiv) x+1/2, y1/2, z+1.
(PCF2) [2.2]paracyclophane-4,15-disulfonic anhydride top
Crystal data top
C16H14S2O5.1/2CH2Cl2F(000) = 1496
Mr = 392.9Dx = 1.641 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2ycCell parameters from 23 reflections
a = 15.927 (2) Åθ = 40.0–44.9°
b = 7.7031 (4) ŵ = 4.80 mm1
c = 26.257 (2) ÅT = 211 K
β = 98.17 (1)°Plate, colourless
V = 3188.7 (5) Å30.88 × 0.25 × 0.06 mm
Z = 8
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 59.9°, θmin = 3.4°
Graphite monochromatorh = 1717
θ/2θ scansk = 08
2357 measured reflectionsl = 029
2357 independent reflections2 standard reflections every 60 min
2176 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullRiding
R[F2 > 2σ(F2)] = 0.061 1/[7.6 + 0.0038*σ(Fobs)2 + 0.00002/σ(Fobs)]
wR(F2) = 0.067(Δ/σ)max = 0.337
S = 0.98Δρmax = 0.88 e Å3
2125 reflectionsΔρmin = 0.55 e Å3
283 parametersExtinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
15 restraintsExtinction coefficient: 1435 (92)
Crystal data top
C16H14S2O5.1/2CH2Cl2V = 3188.7 (5) Å3
Mr = 392.9Z = 8
Monoclinic, C2/cCu Kα radiation
a = 15.927 (2) ŵ = 4.80 mm1
b = 7.7031 (4) ÅT = 211 K
c = 26.257 (2) Å0.88 × 0.25 × 0.06 mm
β = 98.17 (1)°
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
2357 measured reflectionsθmax = 59.9°
2357 independent reflections2 standard reflections every 60 min
2176 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.06115 restraints
wR(F2) = 0.067Riding
S = 0.98(Δ/σ)max = 0.337
2125 reflectionsΔρmax = 0.88 e Å3
283 parametersΔρmin = 0.55 e Å3
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3727 (4)0.4668 (8)0.3312 (2)0.034 (3)
C20.3458 (3)0.4004 (7)0.3811 (2)0.029 (3)
C30.4010 (3)0.3482 (7)0.4235 (2)0.028 (3)
C40.3774 (4)0.2244 (8)0.4589 (2)0.031 (3)
C50.2953 (3)0.1569 (8)0.4507 (2)0.032 (3)
C60.2358 (4)0.2393 (8)0.4160 (2)0.034 (3)
C70.2605 (4)0.3608 (8)0.3814 (2)0.033 (3)
C80.2778 (4)0.0220 (9)0.4720 (2)0.040 (3)
C90.3935 (4)0.3110 (8)0.2941 (2)0.034 (3)
C100.3781 (3)0.1324 (8)0.3162 (2)0.030 (3)
C110.4344 (3)0.0524 (7)0.3539 (2)0.028 (3)
C120.4076 (4)0.0680 (7)0.3883 (2)0.031 (3)
C130.3218 (3)0.1084 (7)0.3844 (2)0.030 (3)
C140.2700 (4)0.0605 (8)0.3406 (2)0.035 (3)
C150.2978 (4)0.0597 (8)0.3065 (2)0.034 (3)
C160.2860 (4)0.1735 (9)0.4317 (2)0.040 (3)
S10.50861 (8)0.4039 (2)0.43174 (5)0.0325 (8)
S20.54240 (8)0.1101 (2)0.36609 (6)0.0333 (8)
O10.5209 (3)0.5850 (5)0.4222 (2)0.047 (2)
O20.5539 (2)0.3242 (6)0.4752 (2)0.045 (2)
O30.5400 (2)0.3177 (5)0.3798 (1)0.031 (2)
O40.5835 (2)0.0225 (6)0.4094 (2)0.044 (2)
O50.5791 (3)0.1144 (6)0.3194 (2)0.048 (3)
C1s0.500000.205 (2)0.250000.090 (9)
Cl1s0.5686 (1)0.3281 (2)0.29318 (7)0.058 (1)
H1010.426 (2)0.533 (7)0.343 (2)0.04 (2)*
H1020.323 (2)0.525 (6)0.310 (2)0.03 (1)*
H40.423 (2)0.192 (7)0.488 (1)0.02 (1)*
H60.175 (1)0.207 (7)0.408 (2)0.02 (1)*
H70.216 (2)0.395 (6)0.352 (1)0.02 (1)*
H810.320 (2)0.045 (6)0.503 (1)0.02 (1)*
H820.215 (1)0.03 (1)0.472 (3)0.07 (2)*
H910.4561 (9)0.316 (8)0.294 (2)0.04 (2)*
H920.353 (2)0.320 (6)0.261 (1)0.01 (1)*
H120.451 (2)0.103 (6)0.418 (1)0.01 (1)*
H140.208 (1)0.088 (8)0.332 (2)0.04 (2)*
H150.252 (2)0.097 (7)0.278 (1)0.03 (2)*
H1610.327 (3)0.251 (6)0.453 (2)0.04 (2)*
H1620.229 (2)0.223 (7)0.419 (2)0.04 (2)*
H1s0.515 (6)0.319 (4)0.236 (3)0.08 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (3)0.033 (3)0.035 (3)0.004 (3)0.005 (3)0.003 (3)
C20.028 (3)0.023 (3)0.036 (3)0.005 (2)0.008 (2)0.006 (3)
C30.025 (3)0.026 (3)0.033 (3)0.000 (2)0.009 (2)0.010 (2)
C40.032 (3)0.034 (3)0.028 (3)0.004 (3)0.006 (2)0.005 (3)
C50.030 (3)0.040 (4)0.029 (3)0.000 (3)0.012 (2)0.006 (3)
C60.025 (3)0.039 (4)0.039 (3)0.001 (3)0.011 (3)0.008 (3)
C70.027 (3)0.034 (3)0.038 (3)0.007 (3)0.003 (2)0.006 (3)
C80.042 (4)0.042 (4)0.039 (4)0.008 (3)0.012 (3)0.007 (3)
C90.037 (3)0.038 (4)0.029 (3)0.003 (3)0.008 (3)0.004 (3)
C100.032 (3)0.035 (3)0.024 (3)0.001 (3)0.008 (2)0.009 (3)
C110.024 (3)0.029 (3)0.030 (3)0.002 (2)0.005 (2)0.010 (3)
C120.031 (3)0.025 (3)0.036 (3)0.004 (3)0.000 (2)0.006 (3)
C130.031 (3)0.022 (3)0.038 (3)0.000 (2)0.003 (3)0.007 (3)
C140.026 (3)0.036 (4)0.043 (4)0.003 (3)0.002 (3)0.010 (3)
C150.031 (3)0.041 (4)0.030 (3)0.003 (3)0.000 (2)0.007 (3)
C160.041 (4)0.036 (4)0.044 (4)0.007 (3)0.007 (3)0.007 (3)
S10.0247 (7)0.0372 (9)0.0356 (8)0.0025 (6)0.0049 (6)0.0080 (7)
S20.0237 (7)0.0352 (8)0.0420 (8)0.0040 (6)0.0080 (6)0.0066 (7)
O10.048 (3)0.029 (2)0.066 (3)0.011 (2)0.019 (2)0.008 (2)
O20.026 (2)0.066 (3)0.040 (2)0.003 (2)0.003 (2)0.009 (2)
O30.031 (2)0.026 (2)0.038 (2)0.002 (2)0.014 (2)0.009 (2)
O40.025 (2)0.050 (3)0.056 (3)0.013 (2)0.003 (2)0.001 (2)
O50.043 (2)0.055 (3)0.051 (3)0.003 (2)0.026 (2)0.012 (2)
C1s0.14 (1)0.032 (6)0.079 (9)0.000000.049 (9)0.00000
Cl1s0.051 (1)0.054 (1)0.064 (1)0.0013 (9)0.0106 (8)0.0029 (9)
Geometric parameters (Å, º) top
C1—H1021.00 (4)C10—C111.383 (7)
C1—H1011.00 (4)C10—C151.386 (8)
C1—C21.523 (9)C11—C121.403 (8)
C1—C91.610 (9)C11—S21.761 (5)
C2—C31.377 (7)C12—H121.00 (3)
C2—C71.394 (8)C12—C131.392 (8)
C3—C41.418 (8)C13—C141.368 (8)
C3—S11.750 (5)C13—C161.523 (9)
C4—H41.00 (3)C14—H141.00 (2)
C4—C51.396 (8)C14—C151.403 (9)
C5—C61.372 (8)C15—H151.00 (4)
C5—C81.528 (9)C16—H1611.00 (5)
C6—H61.00 (2)C16—H1621.00 (3)
C6—C71.398 (9)S1—O21.402 (4)
C7—H71.00 (3)S1—O11.436 (5)
C8—H821.00 (2)S1—O31.657 (4)
C8—H811.00 (3)S2—O41.403 (4)
C8—C161.594 (9)S2—O51.431 (5)
C9—H911.00 (2)S2—O31.640 (4)
C9—H921.00 (3)C1s—H1s1.00 (5)
C9—C101.526 (9)C1s—Cl1s1.741 (7)
Cl1s···H1s1.61 (8)H92···H1siv3.48 (7)
H161···H1621.70 (6)H6···H81xiii3.48 (7)
H101···H1021.74 (5)C8···H162vi3.48 (5)
H91···H921.74 (4)H7···H923.49 (5)
H81···H821.76 (4)C13···H63.49 (4)
C16···H821.99 (6)C11···S13.495 (6)
C2···H1012.01 (5)C12···H813.50 (3)
C15···H142.01 (4)C1s···H101x3.51 (5)
C7···H62.02 (4)C1s···H101xiv3.51 (5)
C14···H152.02 (4)C10···H73.51 (4)
C10···H912.02 (5)O5···H162v3.51 (4)
C8···H1612.03 (5)H101···H1siii3.5 (1)
C10···H922.04 (4)O1···H161iii3.52 (5)
C11···H122.04 (4)C5···H82xiii3.53 (8)
C13···H1622.04 (4)H101···H73.54 (5)
C6···H72.05 (4)O1···O4iii3.544 (6)
C5···H822.05 (6)H102···H153.54 (7)
C3···H42.06 (4)O2···O2ix3.552 (7)
C9···H1022.07 (5)C8···O4ii3.552 (7)
H82···H1622.07 (9)C9···H15i3.55 (4)
C2···H1022.08 (4)Cl1s···H91xiv3.56 (6)
C5···H812.08 (4)H91···H92viii3.56 (5)
H81···H1612.09 (7)C9···H91viii3.56 (5)
C2···H72.09 (3)C6···H1623.56 (6)
C13···H1612.09 (5)C9···H14i3.57 (5)
C1···H912.11 (5)C3···H123.57 (5)
C13···H142.11 (3)H102···H14iii3.59 (7)
C5···H62.11 (3)C1···H153.60 (5)
C10···H152.12 (4)Cl1s···H102xiv3.60 (4)
C13···H122.12 (3)C7···H161iii3.61 (5)
C16···H812.13 (4)C15···H1023.61 (5)
H102···H922.13 (6)H161···H162vi3.61 (8)
C1···H922.14 (3)C4···O33.614 (7)
C5···H42.14 (3)C4···O1ix3.619 (7)
C8···H1622.15 (5)O3···H82v3.62 (5)
C9···H1012.16 (5)O3···Cl1siii3.622 (4)
H14···H152.19 (7)H91···H153.63 (5)
H101···H912.21 (8)C14···H73.63 (5)
H6···H72.24 (6)O1···Cl1siii3.637 (5)
C11···C152.349 (7)C3···H913.64 (6)
O4···H122.35 (4)S1···H6v3.64 (4)
C3···C72.353 (7)C11···C1s3.643 (9)
C12···C142.366 (8)C6···O1xv3.648 (7)
O3···O52.374 (6)S1···H913.66 (6)
H102···H72.37 (6)C2···H162iii3.66 (5)
C4···C62.376 (8)C3···O2ix3.663 (7)
O1···O32.380 (6)C12···O33.668 (7)
O2···H42.39 (4)C8···O2ii3.670 (8)
C13···C152.406 (8)C7···O5xii3.671 (7)
C5···C72.407 (8)C7···H923.67 (3)
C11···C132.409 (8)C14···H823.69 (7)
O1···H1012.42 (5)C6···H82xiii3.69 (7)
C3···C52.420 (8)C5···C113.690 (8)
C10···C142.428 (8)C6···C8xiii3.691 (9)
C2···C62.429 (8)C1···C13iii3.693 (8)
H92···H152.43 (6)C5···C6xiii3.693 (8)
C10···C122.437 (8)C8···C16vi3.70 (1)
C2···C42.443 (8)O3···H6v3.70 (4)
O3···H912.45 (5)S1···H162v3.70 (3)
O1···O22.458 (6)C11···H43.70 (4)
O4···O52.459 (6)C9···Cl1siv3.707 (7)
O3···O42.470 (6)C8···H143.71 (5)
H14···H1622.48 (8)C11···H1013.71 (5)
O2···O32.483 (6)C2···H153.71 (4)
H6···H822.49 (9)C2···C16iii3.715 (9)
C1···C72.503 (9)C15···H63.72 (4)
C9···C152.513 (9)C15···Cl1sxii3.720 (6)
O5···H912.52 (4)C10···O5viii3.721 (7)
C12···C162.518 (9)S2···H14v3.72 (4)
H4···H812.52 (6)C11···H143.72 (2)
C14···C162.525 (9)O3···H123.72 (4)
C6···C82.526 (9)C5···H143.73 (5)
C4···C82.528 (9)C14···Cl1sxii3.730 (6)
H102···H15i2.53 (6)C4···H6xiii3.73 (5)
O2···H161ii2.54 (5)C16···H43.73 (4)
C15···H922.54 (4)O3···H43.73 (4)
O3···H1012.55 (4)C7···H81xiii3.73 (4)
H12···H1612.56 (6)C3···H63.74 (2)
C9···C112.563 (8)C7···H143.74 (6)
C1···C32.569 (8)O4···H43.74 (4)
C7···H1022.57 (5)C2···C123.738 (8)
C14···H1622.57 (5)C7···C133.742 (8)
H82···H1612.58 (8)C12···H153.75 (4)
O4···H81ii2.58 (3)C15···H123.75 (3)
C8···C132.585 (9)C8···H82vi3.75 (8)
C6···H822.59 (8)C5···C8xiii3.749 (9)
C5···C162.594 (9)C4···H1613.75 (5)
C2···C92.601 (8)C13···H43.75 (4)
C4···H812.60 (5)Cl1s···H101xiv3.75 (6)
C1···C102.609 (9)S2···H1013.75 (5)
C11···O42.613 (6)C7···H43.76 (4)
H92···H14i2.62 (6)C12···O53.756 (8)
C3···O22.620 (6)C4···H73.76 (3)
C3···H1012.62 (6)C1···Cl1siii3.757 (7)
C11···H912.62 (6)C1···C63.762 (9)
C11···O52.637 (7)C11···C163.763 (9)
O1···H12iii2.64 (4)C6···C123.766 (8)
C3···O32.645 (7)C8···O2xv3.771 (8)
C3···O12.645 (7)C9···C143.772 (9)
H101···H1siv2.7 (1)C7···C83.774 (9)
C12···H1612.66 (5)C15···C163.775 (9)
C11···O32.672 (6)C8···H81vi3.78 (5)
S2···H122.68 (4)C3···C83.783 (9)
C12···S22.681 (6)C3···H82xiii3.79 (7)
C1···H72.68 (4)C6···C103.790 (8)
C4···S12.685 (6)C16···H161vi3.79 (5)
O1···H6v2.69 (3)C7···C113.795 (8)
S1···H1012.69 (5)C5···H81xiii3.80 (5)
S1···H42.69 (4)C2···C13iii3.805 (8)
S2···H912.69 (5)C10···C1s3.81 (1)
C11···C142.734 (8)C4···O13.807 (7)
H102···H912.74 (6)C5···H6xiii3.81 (5)
C2···S12.741 (5)C9···C123.812 (8)
C3···C62.742 (8)C4···C103.814 (8)
C12···C152.753 (8)C6···H153.82 (4)
H82···H161vi2.75 (9)C7···C16iii3.824 (9)
C5···C132.756 (8)C3···C133.828 (8)
C10···S22.760 (5)C1···C43.828 (8)
C4···C72.763 (8)S2···H6vii3.83 (4)
C16···H122.77 (4)S2···H81ii3.83 (3)
C9···H152.77 (4)S1···H4ix3.83 (5)
C2···C102.772 (8)C7···Cl1sxii3.849 (6)
C8···H62.79 (4)C2···C143.851 (8)
O5···H7vii2.80 (4)O2···H4ix3.86 (5)
C16···H142.80 (5)C6···H4xiii3.86 (4)
C10···C132.814 (8)C1···Cl1siv3.861 (7)
C2···C52.814 (8)O5···H1sviii3.87 (5)
O2···H82v2.82 (4)C5···C153.866 (8)
H101···H922.82 (6)C1···S23.871 (6)
C8···H42.82 (4)C11···H1sviii3.87 (6)
H92···H15i2.82 (6)C9···H1siii3.87 (7)
H81···H1622.83 (6)S2···C1s3.879 (8)
O4···H6vii2.84 (5)C9···S13.880 (6)
C12···O42.862 (7)C12···H102x3.88 (5)
H91···H91viii2.87 (7)O2···H123.88 (4)
C4···O22.886 (7)O5···H123.88 (4)
H81···H162vi2.90 (7)C2···O23.886 (6)
Cl1s···Cl1sviii2.916 (2)C10···O43.890 (6)
O4···H7vii2.94 (4)S1···H161ii3.89 (5)
S1···S22.940 (2)C1···C12iii3.894 (8)
O2···H81ii2.94 (4)C3···O43.896 (7)
O1···H4ix2.96 (4)C2···S23.913 (6)
H91···H1siv2.97 (8)S1···H12iii3.91 (5)
O2···O42.972 (6)C6···Cl1sxii3.914 (6)
O5···H92viii2.97 (4)O1···H43.91 (5)
Cl1s···H101x2.98 (5)C14···O5xv3.917 (7)
C4···C122.998 (8)C4···O4ii3.918 (7)
H4···H123.00 (6)S1···S1ix3.924 (2)
C9···O33.004 (6)C14···H923.93 (4)
C1···O33.014 (7)C4···S23.928 (6)
C3···C113.015 (8)S1···O1ix3.932 (5)
O4···H162v3.02 (4)S2···Cl1s3.932 (2)
H4···H12ii3.04 (5)C7···S2xii3.939 (6)
C4···H123.05 (4)C2···C133.940 (8)
O3···H162v3.05 (3)C9···Cl1siii3.940 (7)
Cl1s···H14vii3.06 (4)C6···H1023.95 (5)
Cl1s···H15vii3.06 (4)C5···C103.946 (8)
O5···H14v3.07 (5)C15···H1623.95 (5)
H7···H153.10 (6)C8···H6xiii3.96 (5)
C13···H823.11 (6)C3···C153.956 (8)
C5···C123.118 (8)C8···C8vi3.96 (1)
H6···H143.12 (8)C1s···H91xiv3.96 (6)
Cl1s···H7vii3.14 (4)C1s···H91x3.96 (6)
C6···C143.139 (9)C16···O3xv3.960 (7)
C2···H913.14 (5)C16···O4xv3.961 (8)
C10···H1023.14 (5)O1···H913.96 (6)
C1···H1siv3.15 (8)C1···H1siii3.96 (8)
C7···C153.152 (9)C13···O1x3.966 (7)
C2···C113.158 (8)C7···H823.97 (8)
C13···H813.16 (3)C4···O2ix3.969 (7)
C2···O33.164 (7)O5···H15viii3.97 (4)
C6···C133.171 (8)S2···O13.976 (5)
O1···O2ix3.176 (6)C4···C6xiii3.978 (9)
C2···O13.180 (7)S1···O53.984 (5)
O4···H4ii3.18 (4)C4···C143.985 (8)
H81···H161vi3.18 (6)C5···S13.986 (6)
C5···H1623.18 (5)C13···S23.987 (6)
C5···H1613.19 (5)C4···C5xiii3.988 (8)
C10···O53.193 (7)O3···H923.99 (3)
C15···H73.20 (4)O5···H102vii3.99 (4)
O3···H14v3.20 (4)C14···H101x3.99 (5)
C10···O33.202 (6)C4···C8xiii3.993 (9)
C1···S13.204 (6)S2···H43.99 (4)
O5···C1s3.21 (1)C3···H813.99 (4)
C9···S23.212 (6)C7···S13.999 (6)
C2···H923.22 (3)C16···H7x4.00 (4)
C14···H92xi3.22 (3)O3···H1024.00 (4)
H102···H1siv3.23 (9)C12···H914.00 (6)
C7···C103.232 (8)C1s···H102x4.01 (4)
C10···H1013.23 (5)C1s···H102xiv4.01 (4)
C7···H1013.23 (4)C15···S24.005 (6)
C14···H63.24 (5)C1···H161iii4.01 (5)
C1···O13.241 (7)C4···O44.010 (7)
C8···C123.244 (9)C11···H101x4.01 (5)
C3···C103.247 (8)C1···C14iii4.013 (9)
C6···O4xii3.250 (7)C10···S14.013 (5)
S1···O43.255 (5)S1···H124.01 (5)
C13···H153.26 (4)S1···H161iii4.02 (5)
C15···H913.26 (4)C4···H1014.02 (6)
C7···O4xii3.261 (7)C16···O2xv4.021 (8)
Cl1s···H6vii3.26 (4)C6···C114.024 (8)
C10···H143.27 (4)C7···H82xiii4.03 (7)
C4···C133.269 (8)C12···H824.03 (5)
C12···H43.27 (4)C1···C1siii4.04 (1)
C5···H73.27 (4)C12···H4ii4.04 (3)
C8···H161vi3.27 (5)C7···C124.039 (8)
C3···H73.27 (3)C16···H162vi4.04 (5)
Cl1s···H91x3.27 (5)C11···O24.052 (7)
C12···O1x3.276 (7)C14···O3xv4.054 (7)
C2···H63.28 (3)O4···Cl1s4.057 (5)
S2···O23.288 (5)C12···O2ii4.061 (7)
C11···H153.29 (4)C12···S14.072 (6)
C6···C163.290 (9)C11···Cl1s4.083 (6)
C12···H1623.29 (4)S1···H81ii4.08 (4)
C10···H123.29 (4)C16···C16vi4.09 (1)
S2···H7vii3.29 (4)C15···O5viii4.097 (8)
C14···H123.30 (3)C3···O1ix4.099 (7)
C4···C113.298 (8)S2···H924.11 (3)
C4···H823.30 (5)O5···O5viii4.126 (6)
C2···C153.300 (8)S1···H1024.13 (4)
C14···H1613.30 (5)C3···C16iii4.134 (9)
O2···H12ii3.30 (4)C5···O4ii4.137 (7)
O1···H82v3.30 (3)Cl1s···H102x4.15 (4)
C9···O53.305 (7)C11···O1x4.168 (7)
C11···H923.31 (4)C7···C8xiii4.171 (9)
C12···H143.31 (2)C1···C16iii4.193 (9)
C2···H43.31 (4)C8···O1xv4.196 (8)
H81···H123.31 (5)C9···C15i4.200 (8)
C6···H43.31 (3)C9···C14i4.201 (8)
C2···H161iii3.31 (5)C7···C13iii4.202 (8)
C6···H813.31 (4)C3···C144.209 (8)
C4···H63.32 (2)C2···C12iii4.210 (8)
C5···C143.316 (8)C4···C154.218 (8)
C12···H101x3.32 (5)C16···O1x4.219 (8)
C6···H143.33 (6)C9···O14.236 (7)
O5···H91viii3.34 (6)C12···C1s4.240 (7)
C15···H92xi3.34 (4)C13···O44.248 (7)
C3···H1023.34 (4)C15···C1s4.251 (8)
C3···C123.342 (8)C9···C134.259 (8)
C9···H1siv3.34 (6)C1···C54.261 (9)
C8···H123.34 (4)C1···C15i4.262 (8)
S1···H82v3.35 (2)C10···C164.263 (9)
S2···H162v3.35 (3)C2···C84.264 (9)
O2···H162v3.35 (4)C13···O2ii4.266 (7)
C7···C93.356 (9)S2···H92viii4.27 (3)
C16···H81vi3.37 (4)C6···S2xii4.269 (6)
C1···C113.368 (8)C12···O24.272 (7)
C7···H153.37 (4)C4···S1ix4.274 (6)
C6···H81xiii3.37 (4)C5···O24.276 (7)
C1···C153.385 (9)S2···H1sviii4.28 (5)
H91···H1siii3.39 (8)C8···C114.285 (9)
Cl1s···H92xiv3.39 (4)C8···S1xv4.306 (7)
C15···H102xi3.39 (4)C1···O54.309 (8)
C3···C93.395 (8)C3···S1ix4.314 (5)
C5···H123.40 (4)C12···Cl1s4.318 (6)
H81···H82vi3.40 (9)C7···C164.324 (9)
H101···H12iii3.41 (7)C9···C1siii4.32 (1)
C16···H82vi3.41 (8)S2···O1x4.335 (5)
C1···H15i3.41 (4)C16···S2xv4.346 (6)
H4···H6xiii3.41 (6)O5···Cl1siii4.349 (5)
C7···H162iii3.41 (5)C5···O1xv4.362 (7)
C3···S23.416 (6)C9···C9viii4.372 (9)
H7···H162iii3.42 (7)C8···O3xv4.373 (7)
H6···H1623.42 (7)C6···C94.374 (9)
C3···H161iii3.42 (5)C6···C6xiii4.375 (8)
C4···C163.425 (9)C6···O5xii4.383 (7)
C9···O5viii3.426 (8)C1···C124.392 (8)
C14···H102x3.43 (5)C1···C144.398 (9)
C7···C143.428 (9)S1···Cl1siii4.404 (2)
C4···H82xiii3.43 (7)C5···O4xii4.410 (7)
C13···H102x3.43 (5)C2···C14iii4.412 (8)
C16···H63.43 (5)C4···C94.420 (8)
H82···H162vi3.45 (9)C3···C8xiii4.434 (9)
C8···C143.449 (9)C3···C164.435 (9)
C5···C5xiii3.451 (8)C16···S1xv4.458 (7)
C9···H73.45 (4)C12···S1x4.462 (6)
C6···C153.459 (9)C6···S14.488 (6)
S1···O2ix3.470 (5)C14···S24.491 (6)
C13···H101x3.47 (5)C6···S1xv4.513 (6)
C16···O2ii3.473 (7)C14···S2xv4.552 (6)
O5···Cl1s3.477 (5)S2···Cl1siii4.774 (2)
H102—C1—H101121 (4)C11—C10—C9123.5 (5)
H102—C1—C2109 (3)C15—C10—C9119.2 (5)
H102—C1—C9102 (3)C10—C11—C12122.1 (5)
H101—C1—C2103 (3)C10—C11—S2122.3 (4)
H101—C1—C9109 (3)C12—C11—S2115.4 (4)
C2—C1—C9112.2 (5)H12—C12—C13125 (2)
C3—C2—C7116.3 (5)H12—C12—C11116 (2)
C3—C2—C1124.6 (5)C13—C12—C11119.1 (5)
C7—C2—C1118.1 (5)C14—C13—C12118.0 (5)
C2—C3—C4121.8 (5)C14—C13—C16121.6 (5)
C2—C3—S1122.0 (4)C12—C13—C16119.4 (5)
C4—C3—S1115.5 (4)H14—C14—C13126 (3)
H4—C4—C5126 (3)H14—C14—C15113 (3)
H4—C4—C3116 (3)C13—C14—C15120.6 (5)
C5—C4—C3118.6 (5)H15—C15—C10125 (3)
C6—C5—C4118.2 (5)H15—C15—C14114 (3)
C6—C5—C8121.1 (5)C10—C15—C14121.1 (5)
C4—C5—C8119.6 (5)H161—C16—H162117 (4)
H6—C6—C5125 (3)H161—C16—C13111 (3)
H6—C6—C7113 (3)H161—C16—C8101 (3)
C5—C6—C7120.6 (5)H162—C16—C13106 (3)
H7—C7—C2121 (2)H162—C16—C8110 (3)
H7—C7—C6116 (2)C13—C16—C8112.1 (5)
C2—C7—C6120.9 (5)O2—S1—O1120.1 (3)
H82—C8—H81123 (5)O2—S1—O3108.3 (2)
H82—C8—C5107 (5)O2—S1—C3112.0 (3)
H82—C8—C1698 (4)O1—S1—O3100.4 (2)
H81—C8—C5109 (3)O1—S1—C3111.9 (3)
H81—C8—C16108 (3)O3—S1—C3101.8 (2)
C5—C8—C16112.4 (5)O4—S2—O5120.4 (3)
H91—C9—H92121 (4)O4—S2—O3108.3 (2)
H91—C9—C10105 (4)O4—S2—C11110.9 (3)
H91—C9—C1105 (4)O5—S2—O3101.0 (2)
H92—C9—C10106 (3)O5—S2—C11111.0 (3)
H92—C9—C1108 (3)O3—S2—C11103.5 (2)
C10—C9—C1112.6 (5)S2—O3—S1126.2 (3)
C11—C10—C15116.0 (5)H1s—C1s—Cl1s66 (4)
C9—C1—C2—C382.0 (7)H81—C8—C16—C13111 (3)
C9—C1—C2—C786.2 (6)H81—C8—C16—H1616 (4)
H101—C1—C2—C336 (3)H81—C8—C16—H162130 (4)
H101—C1—C2—C7156 (3)H82—C8—C16—C13120 (4)
H102—C1—C2—C3165 (3)H82—C8—C16—H161122 (5)
H102—C1—C2—C726 (3)H82—C8—C16—H1622 (6)
C2—C1—C9—C102.3 (6)C1—C9—C10—C1179.1 (7)
C2—C1—C9—H91111 (4)C1—C9—C10—C1587.3 (6)
C2—C1—C9—H92118 (2)H91—C9—C10—C1135 (4)
H101—C1—C9—C10116 (3)H91—C9—C10—C15159 (4)
H101—C1—C9—H913 (5)H92—C9—C10—C11164 (2)
H101—C1—C9—H92128 (4)H92—C9—C10—C1530 (2)
H102—C1—C9—C10114 (3)C9—C10—C11—C12152.6 (6)
H102—C1—C9—H91132 (4)C9—C10—C11—S221.0 (8)
H102—C1—C9—H921 (4)C15—C10—C11—C1214.1 (8)
C1—C2—C3—C4152.8 (6)C15—C10—C11—S2172.2 (4)
C1—C2—C3—S117.1 (8)C9—C10—C15—C14153.3 (6)
C7—C2—C3—C415.7 (8)C9—C10—C15—H1518 (3)
C7—C2—C3—S1174.4 (4)C11—C10—C15—C1414.1 (9)
C1—C2—C7—C6154.0 (6)C11—C10—C15—H15175 (3)
C1—C2—C7—H711 (3)C10—C11—C12—C130.0 (9)
C3—C2—C7—C615.3 (9)C10—C11—C12—H12170 (3)
C3—C2—C7—H7180 (3)S2—C11—C12—C13174.0 (4)
C2—C3—C4—C51.3 (9)S2—C11—C12—H124 (3)
C2—C3—C4—H4178 (3)C10—C11—S2—O358.1 (5)
S1—C3—C4—C5171.8 (5)C10—C11—S2—O4174.0 (5)
S1—C3—C4—H47 (3)C10—C11—S2—O549.5 (6)
C2—C3—S1—O147.1 (6)C12—C11—S2—O3116.0 (4)
C2—C3—S1—O2174.8 (5)C12—C11—S2—O40.1 (5)
C2—C3—S1—O359.3 (5)C12—C11—S2—O5136.5 (4)
C4—C3—S1—O1142.3 (4)C11—C12—C13—C1414.7 (8)
C4—C3—S1—O24.2 (5)C11—C12—C13—C16154.5 (5)
C4—C3—S1—O3111.2 (4)H12—C12—C13—C14176 (3)
C3—C4—C5—C614.0 (9)H12—C12—C13—C1615 (3)
C3—C4—C5—C8154.5 (6)C12—C13—C14—C1514.8 (9)
H4—C4—C5—C6167 (3)C12—C13—C14—H14176 (4)
H4—C4—C5—C825 (3)C16—C13—C14—C15154.1 (6)
C4—C5—C6—C714.5 (9)C16—C13—C14—H1415 (4)
C4—C5—C6—H6176 (4)C12—C13—C16—C873.8 (7)
C8—C5—C6—C7153.8 (6)C12—C13—C16—H16138 (3)
C8—C5—C6—H615 (4)C12—C13—C16—H162166 (3)
C4—C5—C8—C1691.7 (6)C14—C13—C16—C895.0 (7)
C4—C5—C8—H8128 (2)C14—C13—C16—H161154 (3)
C4—C5—C8—H82162 (4)C14—C13—C16—H16226 (3)
C6—C5—C8—C1676.4 (7)C13—C14—C15—C100.2 (9)
C6—C5—C8—H81164 (2)C13—C14—C15—H15172 (3)
C6—C5—C8—H8229 (5)H14—C14—C15—C10170 (4)
C5—C6—C7—C20.4 (9)H14—C14—C15—H152 (5)
C5—C6—C7—H7166 (3)C3—S1—O3—S264.9 (3)
H6—C6—C7—C2170 (3)O1—S1—O3—S2179.9 (3)
H6—C6—C7—H74 (4)O2—S1—O3—S253.2 (3)
C5—C8—C16—C138.4 (7)C11—S2—O3—S168.4 (3)
C5—C8—C16—H161126 (3)O4—S2—O3—S149.3 (3)
C5—C8—C16—H162110 (3)O5—S2—O3—S1176.7 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) x, y+1, z; (iv) x+1, y+1, z+1/2; (v) x+1/2, y+1/2, z; (vi) x+1/2, y1/2, z+1; (vii) x+1/2, y1/2, z; (viii) x+1, y, z+1/2; (ix) x+1, y+1, z+1; (x) x, y1, z; (xi) x+1/2, y1/2, z+1/2; (xii) x1/2, y+1/2, z; (xiii) x+1/2, y+1/2, z+1; (xiv) x+1, y1, z+1/2; (xv) x1/2, y1/2, z.
(PCF3) [2.2]paracyclophane-4,15-disulfonimide top
Crystal data top
C16H15NS2O4.2CH3CNF(000) = 452
Mr = 431.54Dx = 1.46 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2y1Cell parameters from 23 reflections
a = 8.725 (7) Åθ = 19.0–20.9°
b = 10.259 (7) ŵ = 0.31 mm1
c = 10.950 (6) ÅT = 293 K
β = 92.87 (4)°Rod, colourless
V = 979 (1) Å31.00 × 0.35 × 0.25 mm
Z = 2
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 29.9°, θmin = 1.9°
Graphite monochromatorh = 1212
θ/2θ scansk = 140
2982 measured reflectionsl = 015
2982 independent reflections2 standard reflections every 60 min
2011 reflections with refl observed if I > 2.5 σ(I ) intensity decay: 10%
Refinement top
Refinement on F12 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.056Riding
wR(F2) = 0.064 1/[8.3 + 0.0072*σ(Fobs)2 + 0.00006/σ(Fobs)]
S = 0.76(Δ/σ)max = 0.307
2011 reflectionsΔρmax = 0.55 e Å3
175 parametersΔρmin = 0.58 e Å3
Crystal data top
C16H15NS2O4.2CH3CNV = 979 (1) Å3
Mr = 431.54Z = 2
Monoclinic, P21/mMo Kα radiation
a = 8.725 (7) ŵ = 0.31 mm1
b = 10.259 (7) ÅT = 293 K
c = 10.950 (6) Å1.00 × 0.35 × 0.25 mm
β = 92.87 (4)°
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
2982 measured reflections2 standard reflections every 60 min
2982 independent reflections intensity decay: 10%
2011 reflections with refl observed if I > 2.5 σ(I )
Refinement top
R[F2 > 2σ(F2)] = 0.05612 restraints
wR(F2) = 0.064Riding
S = 0.76(Δ/σ)max = 0.307
2011 reflectionsΔρmax = 0.55 e Å3
175 parametersΔρmin = 0.58 e Å3
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4839 (5)0.6714 (4)0.9760 (3)0.035 (2)
C20.3939 (4)0.6152 (3)0.8666 (3)0.029 (2)
C30.4507 (4)0.6032 (3)0.7490 (3)0.027 (1)
C40.3532 (4)0.6042 (4)0.6441 (3)0.032 (2)
C50.1949 (4)0.6157 (4)0.6545 (4)0.036 (2)
C60.1383 (4)0.5972 (4)0.7699 (4)0.040 (2)
C70.2362 (4)0.5960 (4)0.8737 (4)0.036 (2)
C80.0957 (5)0.6715 (4)0.5493 (4)0.048 (2)
S10.6499 (1)0.60528 (9)0.72663 (8)0.0304 (4)
O10.6727 (3)0.5972 (3)0.5988 (2)0.042 (1)
O20.7298 (3)0.5183 (3)0.8104 (3)0.044 (2)
N0.7121 (5)0.750000.7766 (4)0.030 (2)
C1s0.0669 (9)0.250000.7999 (7)0.054 (4)
C2s0.0351 (7)0.250000.9069 (6)0.044 (3)
C4s0.4696 (9)0.250000.6627 (6)0.051 (4)
N1s0.1164 (7)0.250000.9907 (5)0.066 (4)
C3s0.309 (1)0.250000.6771 (9)0.069 (5)
N2s0.5986 (9)0.250000.6494 (7)0.076 (5)
H110.592 (2)0.638 (5)0.977 (5)0.08000*
H120.431 (5)0.646 (5)1.052 (3)0.08000*
H40.399 (5)0.611 (6)0.562 (2)0.08000*
H60.024 (1)0.602 (6)0.771 (5)0.08000*
H70.195 (5)0.599 (6)0.957 (2)0.08000*
H810.015 (2)0.649 (5)0.560 (4)0.08000*
H820.139 (5)0.649 (5)0.469 (2)0.08000*
H1n0.770 (8)0.750000.858 (3)0.08000*
H11s0.011 (8)0.250000.723 (4)0.08000*
H12s0.131 (5)0.329 (3)0.782 (5)0.08000*
H31s0.274 (9)0.250000.763 (3)0.08000*
H32s0.252 (5)0.328 (3)0.645 (5)0.08000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.047 (2)0.030 (2)0.028 (2)0.001 (2)0.001 (2)0.004 (1)
C20.037 (2)0.016 (1)0.034 (2)0.001 (1)0.001 (1)0.003 (1)
C30.030 (1)0.016 (1)0.035 (2)0.000 (1)0.001 (1)0.000 (1)
C40.039 (2)0.021 (1)0.037 (2)0.003 (1)0.002 (1)0.005 (2)
C50.037 (2)0.022 (2)0.049 (2)0.006 (1)0.008 (2)0.006 (2)
C60.032 (2)0.026 (2)0.063 (2)0.005 (2)0.004 (2)0.003 (2)
C70.041 (2)0.023 (2)0.045 (2)0.002 (2)0.009 (2)0.003 (2)
C80.043 (2)0.043 (2)0.055 (3)0.004 (2)0.017 (2)0.003 (2)
S10.0309 (4)0.0235 (4)0.0369 (4)0.0030 (4)0.0023 (3)0.0022 (4)
O10.048 (2)0.038 (1)0.042 (1)0.002 (1)0.011 (1)0.010 (1)
O20.042 (2)0.030 (1)0.060 (2)0.010 (1)0.005 (1)0.005 (1)
N0.028 (2)0.024 (2)0.037 (2)0.000000.005 (2)0.00000
C1s0.055 (4)0.049 (4)0.055 (4)0.000000.023 (3)0.00000
C2s0.042 (3)0.041 (3)0.050 (4)0.000000.001 (3)0.00000
C4s0.063 (4)0.040 (3)0.048 (4)0.000000.001 (3)0.00000
N1s0.063 (4)0.082 (5)0.050 (3)0.000000.016 (3)0.00000
C3s0.070 (5)0.044 (4)0.094 (7)0.000000.027 (5)0.00000
N2s0.075 (5)0.074 (5)0.079 (5)0.000000.013 (4)0.00000
Geometric parameters (Å, º) top
C1—H121.00 (4)C8—H811.00 (2)
C1—H111.00 (3)C8—C8i1.610 (7)
C1—C21.513 (5)S1—O11.426 (3)
C1—C1i1.613 (5)S1—O21.435 (3)
C2—C71.396 (5)S1—N1.664 (2)
C2—C31.409 (5)N—H1n1.00 (4)
C3—C41.395 (5)C1s—H12sii0.99 (4)
C3—S11.767 (4)C1s—H12s0.99 (4)
C4—H41.00 (3)C1s—H11s1.00 (5)
C4—C51.396 (5)C1s—C2s1.44 (1)
C5—C61.393 (6)C2s—N1s1.131 (9)
C5—C81.519 (6)C4s—N2s1.14 (1)
C6—H61.00 (1)C4s—C3s1.42 (1)
C6—C71.387 (6)C3s—H32sii1.00 (4)
C7—H71.00 (3)C3s—H32s1.00 (4)
C8—H821.00 (3)C3s—H31s1.00 (4)
H11s···H12sii1.50 (7)C8···H4i3.46 (5)
H11s···H12s1.50 (7)S1···H12siv3.46 (4)
H31s···H32sii1.52 (5)N2s···H11siv3.46 (7)
H31s···H32s1.52 (5)H4···H82i3.46 (7)
H32s···H32sii1.60 (5)N2s···H12vi3.47 (3)
H12s···H12sii1.61 (5)N2s···H12iii3.47 (3)
H11···H121.67 (5)C3···S1i3.474 (4)
H81···H821.72 (5)C3···H32s3.47 (4)
N1s···H1niii1.89 (5)C3···H12vi3.49 (5)
C5···H62.02 (3)H11···H73.49 (5)
C2s···H11s2.04 (4)C5···H4i3.50 (5)
C2···H72.05 (4)H81···H32sv3.50 (6)
C2···H122.06 (3)O1···H6iv3.52 (3)
C4s···H32sii2.06 (4)C5···H6i3.53 (5)
C4s···H32s2.06 (4)H6···H823.54 (6)
H82···H82i2.06 (8)C1···C2vi3.546 (5)
C3···H42.07 (3)S1···H81iv3.55 (3)
C2···H112.07 (3)C2s···C3s3.56 (1)
C4s···H31s2.08 (7)C8···H81ix3.56 (5)
H81···H81i2.08 (8)C1···H31sxii3.56 (5)
C5···H812.08 (3)C1···C1vi3.565 (6)
C8···H82i2.08 (5)C2···H1n3.57 (6)
C6···H72.08 (2)C2···H7i3.57 (5)
C8···H81i2.09 (5)C1···N1sxii3.580 (8)
C5···H42.09 (4)H82···H32six3.58 (6)
C5···H822.10 (3)C4···N2sxvii3.588 (8)
C2s···H12sii2.10 (4)C3···H4i3.59 (5)
C2s···H12s2.10 (4)N···H81iv3.60 (4)
C1···H12i2.11 (5)N···H81xv3.60 (4)
C7···H62.12 (3)C2s···H32s3.60 (5)
H12···H12i2.13 (8)C2s···H32sii3.60 (5)
C1···H11i2.17 (5)C1s···C3s3.60 (1)
S1···H1n2.28 (4)C8···N2sxvii3.616 (9)
H11···H11i2.29 (7)C8···H32six3.62 (5)
H12···H72.31 (6)C2s···H11vi3.62 (3)
O2···H12siv2.32 (4)C2s···H11iii3.62 (3)
H6···H812.36 (7)H4···H813.63 (5)
H11···H1n2.37 (7)C6···H12s3.63 (4)
C3···C72.373 (5)C1···O2vi3.630 (5)
C4···C62.383 (6)C4···H82i3.63 (5)
O1···H42.41 (5)S1···H12vi3.64 (4)
O2···N2.409 (3)H12s···H31s3.64 (9)
C3···C52.416 (5)C7···O2vi3.651 (5)
C5···C72.417 (6)C7···H12i3.65 (5)
C2···C62.428 (5)O1···H32sxvii3.65 (4)
C2···C42.447 (5)C8···H12six3.66 (5)
O2···H1n2.45 (1)O1···N2s3.668 (4)
H6···H72.46 (5)N1s···H73.67 (6)
H4···H822.47 (6)N1s···H7ii3.67 (6)
O1···O22.481 (4)C4···C3s3.674 (5)
H11s···H31s2.5 (1)C6···H81i3.68 (5)
C1···C72.507 (6)C4···N3.700 (6)
O1···N2.509 (5)C6···O2xi3.703 (5)
C4···C82.524 (6)C3s···H81xvi3.71 (4)
C6···C82.544 (6)C3s···H81ix3.71 (4)
H82···H11sv2.54 (6)C1s···H6ii3.72 (6)
O2···H112.55 (5)C1s···H63.72 (6)
C3s···N2s2.56 (1)O2···H11siv3.72 (4)
C1s···N1s2.57 (1)C7···H32s3.72 (4)
C7···H122.57 (4)O2···H82vii3.74 (4)
C1···C32.584 (5)C6···H1nxi3.74 (6)
C5···C8i2.597 (6)C6···H7i3.74 (5)
C1···C2i2.598 (5)C3···H63.75 (1)
C3···O12.604 (4)C3···C4s3.750 (4)
H11s···H32sii2.61 (8)C4s···H12siv3.75 (4)
H11s···H32s2.61 (8)C4s···H12sx3.75 (4)
C1···H72.63 (5)C7···H6i3.75 (5)
C8···H62.64 (5)C1···C63.753 (6)
C3···O22.641 (5)C6···H31s3.75 (2)
C6···H812.65 (4)C4···H73.76 (3)
C4···H822.65 (4)C5···O1vii3.759 (5)
C2s···H31s2.68 (7)C3···C5i3.760 (5)
H81···H82i2.69 (7)C7···H43.76 (3)
C4···S12.699 (4)S1···N2s3.763 (3)
O2···H12vi2.70 (4)C3···C83.768 (6)
C8···H42.71 (5)O1···H12siv3.77 (4)
N2s···H4vii2.72 (4)C7···H31s3.77 (1)
N2s···H4viii2.72 (4)C4···C4s3.776 (5)
N···H112.73 (5)C2···C4i3.777 (5)
N···H11i2.73 (5)O2···H12sx3.78 (3)
C3···N2.737 (5)C7···C83.780 (6)
C3···C62.748 (5)C4···O23.780 (5)
C3···H112.75 (5)C1s···H12xiii3.79 (4)
H82···H12six2.75 (6)C1s···H12xiv3.79 (4)
C5···C5i2.755 (5)N···H4i3.79 (4)
O2···H6iv2.76 (2)N···H43.79 (4)
C4···C72.762 (5)C7···C2sxviii3.799 (7)
C2···C2i2.765 (5)C3s···H12iii3.80 (4)
S1···H42.77 (4)C3s···H12vi3.80 (4)
H11···H12i2.77 (7)C3···H11i3.81 (5)
C2···S12.774 (4)O1···H81xv3.81 (4)
N1s···H11iii2.79 (3)C5···C7i3.814 (6)
N1s···H11vi2.79 (3)C2···C6i3.816 (5)
O1···H4vii2.82 (5)C1···C43.817 (5)
N2s···H12siv2.83 (4)C6···H11s3.82 (2)
N2s···H12sx2.83 (4)C7···N1sxviii3.824 (7)
C2···C52.829 (5)C8···O1vii3.827 (6)
O1···H81iv2.83 (2)C8···O1xi3.833 (6)
S1···H112.83 (5)O1···H4i3.84 (5)
H4···H4i2.86 (8)O1···N2sxvii3.848 (7)
C4···O12.857 (5)S1···H11i3.85 (5)
C3s···H11s2.86 (7)C6···N1sxviii3.854 (7)
O2···H7vi2.87 (3)O2···H81iv3.86 (4)
N2s···H82viii2.87 (5)S1···H4vii3.87 (4)
N2s···H82vii2.87 (5)O2···C4s3.870 (6)
H6···H1nxi2.88 (7)C5···H81ix3.87 (5)
O1···H32svii2.89 (5)C2s···H73.87 (6)
N···N1sxii2.890 (7)C2s···H7ii3.87 (6)
N1s···H31s2.91 (5)C8···H82ix3.88 (5)
H11···H12vi2.94 (7)C7···H12vi3.88 (5)
C4···H32s2.97 (4)C4···C6i3.881 (6)
S1···S1i2.970 (2)C5···C3s3.886 (5)
C1···H1n2.98 (6)C3···C7i3.892 (5)
C2s···H7xiii2.99 (5)C4···H4vii3.89 (5)
C2s···H7xiv2.99 (5)C2s···H6xiv3.89 (5)
H81···H32six2.99 (6)C2s···H6xiii3.89 (5)
C4···C4i2.992 (6)S1···H82vii3.90 (5)
C5···H32s3.00 (3)N1s···C3s3.90 (1)
C3···C3i3.013 (5)C3···C3s3.897 (5)
C2s···H1niii3.01 (5)C1···S1i3.898 (4)
C1s···H31s3.02 (8)C4s···H43.90 (6)
H7···H12sxiii3.03 (6)C4s···H4ii3.90 (6)
H6···H6i3.03 (8)C8···C1sv3.903 (9)
N1s···H11s3.09 (5)C8···H32s3.90 (4)
H7···H7i3.09 (8)C2s···H6ii3.91 (6)
C4···H4i3.09 (6)C2s···H63.91 (6)
C2···H11vi3.11 (5)C2···O13.907 (5)
C4s···H4vii3.12 (4)C4s···H82vii3.91 (5)
C4s···H4viii3.12 (4)C4s···H82viii3.91 (5)
N···H6xv3.12 (3)S1···N1sxii3.913 (6)
N···H6iv3.12 (3)C3···H11vi3.92 (5)
H6···H12s3.12 (6)C4···H31s3.93 (2)
O1···H82vii3.12 (5)C7···N1s3.933 (5)
N2s···H32s3.13 (5)C6···H123.93 (4)
N2s···H32sii3.13 (5)O2···C2siv3.938 (6)
H11···H7vi3.13 (7)C3···H31s3.94 (3)
C1···N3.133 (6)C2···C5i3.952 (5)
O1···O1i3.134 (5)C8···H32sv3.96 (4)
C8···H11sv3.14 (4)C2···H32s3.97 (4)
C6···C6i3.136 (6)C1···C7vi3.975 (6)
N2s···H31s3.15 (7)O2···H43.98 (4)
C1s···H82ix3.15 (3)C5···H31s3.98 (2)
C1s···H82xvi3.15 (3)C7···C2s3.985 (5)
C7···C7i3.159 (6)C6···C2s3.985 (6)
N1s···H12s3.17 (5)C2···S1i3.988 (4)
N1s···H12sii3.17 (5)C1···H7vi3.99 (5)
C5···H81i3.17 (5)C2···O2vi3.992 (5)
C5···H82i3.18 (5)C8···H12sv4.00 (5)
C2···H12i3.18 (5)C3s···H44.00 (6)
C2···O23.185 (5)C3s···H4ii4.00 (6)
C4···C5i3.193 (6)C7···H12sxiii4.00 (5)
C2···H12vi3.19 (5)C6···C1s4.007 (6)
N1s···H7xiv3.20 (5)C5···S14.010 (5)
N1s···H7xiii3.20 (5)C6···C3s4.010 (6)
C2···C3i3.212 (5)C3s···H11vi4.01 (5)
H4···H4vii3.23 (7)C3s···H11iii4.01 (5)
C1···S13.226 (4)C7···H814.01 (4)
C7···H11vi3.23 (5)C3s···H4vii4.01 (4)
H11···H31sxii3.24 (6)C3s···H4viii4.01 (4)
C6···H6i3.24 (6)N···C2sxii4.014 (8)
C5···C6i3.252 (6)C3···N2s4.016 (5)
C4···H63.26 (3)S1···H4i4.02 (5)
H81···H82ix3.26 (7)S1···C4s4.018 (4)
C6···H32s3.26 (4)C8···C8ix4.020 (7)
C2···H11i3.26 (5)C4···S1i4.021 (4)
C2···C7i3.269 (5)S1···O2i4.022 (4)
C3···H73.27 (4)C3···H824.02 (4)
H12···H12sxiii3.27 (6)C7···S14.027 (5)
S1···H6iv3.27 (1)C3···O1i4.028 (5)
C1···O23.278 (5)C1···C4sxii4.039 (8)
C1s···N2sxi3.28 (1)C2···H31s4.04 (2)
C7···H7i3.28 (6)C6···Nxi4.040 (6)
O2···C1siv3.280 (5)C4···C4sxvii4.054 (8)
C7···H113.28 (3)O1···C4s4.055 (5)
H81···H11sv3.29 (6)C5···N2sxvii4.101 (8)
C1···H11vi3.29 (5)C3···C6i4.123 (6)
C2···N3.296 (6)C2···C2vi4.124 (5)
C6···H43.30 (4)C4···C7i4.133 (6)
N1s···H6xiv3.30 (5)O1···O1vii4.135 (4)
N1s···H6xiii3.30 (5)C1···C3vi4.142 (5)
H82···H12sv3.30 (6)S1···H124.14 (4)
C3···C4i3.311 (5)C4···O1i4.188 (5)
H11···H11vi3.31 (7)C1···C3sxii4.20 (1)
O1···H1n3.31 (3)C7···C3s4.216 (7)
C5···H73.32 (2)C4···N2s4.216 (6)
H4···H32s3.32 (7)S1···H7vi4.22 (4)
C1s···H7xiii3.32 (4)C6···C2sxviii4.219 (8)
C1s···H7xiv3.32 (4)C7···C1sxviii4.241 (8)
C4···H813.32 (2)C1s···C4sxi4.24 (1)
C3···H1n3.33 (6)C5···O14.248 (6)
C2···H43.34 (2)S1···H32svii4.26 (5)
H81···H81ix3.34 (8)C1···C54.264 (6)
C6···H823.34 (3)C6···S1xi4.265 (5)
C4···C8i3.345 (6)C2···C84.275 (6)
C2···H63.35 (2)C1···N2sxii4.278 (8)
C3···H123.36 (3)C8···C3sv4.29 (1)
C1···H12vi3.36 (5)C1···O2i4.291 (5)
C4···O1vii3.367 (5)C6···N1s4.314 (6)
S1···O1i3.367 (4)C2···C3s4.330 (6)
C1···C7i3.373 (6)O2···C2sxii4.337 (6)
H12···H31sxii3.38 (7)C8···Nxi4.345 (7)
C4s···H12vi3.38 (3)C3···C8i4.364 (6)
C4s···H12iii3.38 (3)C1···C6i4.375 (6)
C6···C8i3.394 (6)C6···O1xi4.387 (5)
C1···C3i3.396 (5)C1···C2sxii4.401 (8)
O1···C3sxvii3.414 (9)C7···C8i4.402 (6)
C1s···H32s3.42 (5)C1···C4i4.404 (5)
C1s···H32sii3.42 (5)C5···C8ix4.420 (6)
O2···N2s3.434 (5)C2···C4s4.429 (5)
C6···C7i3.440 (6)S1···C1siv4.454 (5)
C8···H6i3.44 (5)C8···S1xi4.486 (6)
O1···C4sxvii3.441 (7)C6···S14.514 (5)
H12···H12vi3.45 (7)C1···S1vi4.517 (4)
C1···H7i3.45 (5)S1···C4sxvii4.585 (7)
H6···H81i3.45 (7)C4···S1vii4.592 (4)
O2···N1sxii3.450 (5)S1···C3sxvii4.69 (1)
H12···H7i3.45 (7)
H12—C1—H11112 (4)H81—C8—C5109 (3)
H12—C1—C2108 (2)H81—C8—C8i104 (3)
H12—C1—C1i105 (3)C5—C8—C8i112.1 (3)
H11—C1—C2109 (3)O1—S1—O2120.3 (2)
H11—C1—C1i110 (3)O1—S1—N108.4 (2)
C2—C1—C1i112.4 (3)O1—S1—C3108.8 (2)
C7—C2—C3115.6 (3)O2—S1—N101.8 (2)
C7—C2—C1119.0 (3)O2—S1—C3110.7 (2)
C3—C2—C1124.3 (3)N—S1—C3105.8 (2)
C4—C3—C2121.6 (3)H1n—N—S1i115.7 (5)
C4—C3—S1116.7 (3)H1n—N—S1115.7 (5)
C2—C3—S1121.3 (2)S1i—N—S1126.4 (3)
H4—C4—C3119 (2)H12sii—C1s—H12s109 (3)
H4—C4—C5120 (2)H12sii—C1s—H11s97 (4)
C3—C4—C5119.9 (3)H12sii—C1s—C2s119 (3)
C6—C5—C4117.4 (3)H12s—C1s—H11s97 (4)
C6—C5—C8121.7 (3)H12s—C1s—C2s119 (3)
C4—C5—C8119.9 (4)H11s—C1s—C2s113 (4)
H6—C6—C7124 (3)N1s—C2s—C1s179.4 (7)
H6—C6—C5114 (3)N2s—C4s—C3s179.0 (8)
C7—C6—C5120.8 (3)H32sii—C3s—H32s107 (4)
H7—C7—C6121 (2)H32sii—C3s—H31s99 (4)
H7—C7—C2117 (3)H32sii—C3s—C4s116 (3)
C6—C7—C2121.5 (4)H32s—C3s—H31s99 (4)
H82—C8—H81118 (4)H32s—C3s—C4s116 (3)
H82—C8—C5111 (3)H31s—C3s—C4s117 (4)
H82—C8—C8i103 (3)
H11—C1—C2—C342 (3)H4—C4—C5—C815 (4)
H11—C1—C2—C7151 (3)C4—C5—C6—C713.8 (6)
H12—C1—C2—C3164 (3)C4—C5—C6—H6177 (4)
H12—C1—C2—C728 (3)C8—C5—C6—C7154.6 (4)
C1i—C1—C2—C380.4 (4)C8—C5—C6—H614 (4)
C1i—C1—C2—C786.9 (4)C4—C5—C8—H81163 (3)
C1—C2—C3—C4152.6 (3)C4—C5—C8—H8232 (3)
C1—C2—C3—S119.9 (5)C4—C5—C8—C8i82.6 (5)
C7—C2—C3—C415.1 (5)C6—C5—C8—H8129 (3)
C7—C2—C3—S1172.4 (3)C6—C5—C8—H82160 (3)
C1—C2—C7—C6153.3 (4)C6—C5—C8—C8i85.6 (5)
C1—C2—C7—H715 (4)C5—C6—C7—C20.9 (6)
C3—C2—C7—C615.2 (5)C5—C6—C7—H7168 (4)
C3—C2—C7—H7177 (4)H6—C6—C7—C2167 (4)
C2—C3—C4—C50.8 (5)H6—C6—C7—H70 (6)
C2—C3—C4—H4170 (4)C3—S1—N—H1n104 (4)
S1—C3—C4—C5173.6 (3)C3—S1—N—S1i57.9 (4)
S1—C3—C4—H43 (4)O1—S1—N—H1n139 (4)
C2—C3—S1—O1177.4 (3)O1—S1—N—S1i58.6 (4)
C2—C3—S1—O248.3 (3)O2—S1—N—H1n11 (4)
C2—C3—S1—N61.2 (3)O2—S1—N—S1i173.7 (3)
C4—C3—S1—O14.6 (3)H11s—C1s—C2s—N1s0.0001 (1)
C4—C3—S1—O2138.8 (3)H12s—C1s—C2s—N1s112 (3)
C4—C3—S1—N111.7 (3)H12sii—C1s—C2s—N1s112 (3)
C3—C4—C5—C613.8 (5)N2s—C4s—C3s—H31s180.0000
C3—C4—C5—C8154.9 (4)N2s—C4s—C3s—H32s64 (3)
H4—C4—C5—C6176 (4)N2s—C4s—C3s—H32sii64 (3)
Symmetry codes: (i) x, y+3/2, z; (ii) x, y+1/2, z; (iii) x+1, y1/2, z+2; (iv) x+1, y, z; (v) x, y+1/2, z+1; (vi) x+1, y+1, z+2; (vii) x+1, y+1, z+1; (viii) x+1, y1/2, z+1; (ix) x, y+1, z+1; (x) x+1, y+1/2, z; (xi) x1, y, z; (xii) x+1, y+1/2, z+2; (xiii) x, y+1, z+2; (xiv) x, y1/2, z+2; (xv) x+1, y+3/2, z; (xvi) x, y1/2, z+1; (xvii) x+1, y+1/2, z+1; (xviii) x, y+1/2, z+2.
(PCF4) N-n-propyl-[2.2]paracyclophane-4,15-disulfonimide top
Crystal data top
C19H21NS2O4F(000) = 824
Mr = 391.5Dx = 1.457 Mg m3
Orthorhombic, PmcnCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P -2n 21Cell parameters from 23 reflections
a = 10.587 (2) Åθ = 25.0–38.5°
b = 10.779 (3) ŵ = 2.92 mm1
c = 15.644 (5) ÅT = 293 K
V = 1785.3 (8) Å3Block, colourless
Z = 40.30 × 0.25 × 0.10 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 74.7°, θmin = 5.0°
Graphite monochromatorh = 013
θ/2θ scansk = 013
1939 measured reflectionsl = 190
1939 independent reflections2 standard reflections every 60 min
804 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullRiding
R[F2 > 2σ(F2)] = 0.089 1/[3.7 + 0.027*σ(Fobs)2 + 0.0009/σ(Fobs)]
wR(F2) = 0.095(Δ/σ)max = 0.021
S = 0.87Δρmax = 0.59 e Å3
804 reflectionsΔρmin = 0.49 e Å3
125 parametersExtinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
11 restraintsExtinction coefficient: 398 (103)
Crystal data top
C19H21NS2O4V = 1785.3 (8) Å3
Mr = 391.5Z = 4
Orthorhombic, PmcnCu Kα radiation
a = 10.587 (2) ŵ = 2.92 mm1
b = 10.779 (3) ÅT = 293 K
c = 15.644 (5) Å0.30 × 0.25 × 0.10 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
1939 measured reflections2 standard reflections every 60 min
1939 independent reflections intensity decay: none
804 reflections with refl observed if I > 2.5 σ(I )
Refinement top
R[F2 > 2σ(F2)] = 0.08911 restraints
wR(F2) = 0.095Riding
S = 0.87Δρmax = 0.59 e Å3
804 reflectionsΔρmin = 0.49 e Å3
125 parameters
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3236 (11)0.4824 (9)0.9901 (4)0.040 (7)
C20.3806 (12)0.3594 (10)0.9641 (7)0.037 (6)
C30.3883 (13)0.3177 (10)0.8768 (6)0.037 (6)
C40.3889 (14)0.1930 (11)0.8542 (5)0.045 (7)
C50.3804 (13)0.1023 (11)0.9182 (8)0.048 (7)
C60.3966 (13)0.1402 (10)1.0036 (7)0.045 (7)
C70.3996 (12)0.2656 (10)1.0245 (5)0.039 (7)
C80.3210 (12)0.0236 (9)0.8971 (5)0.061 (9)
C170.250000.6334 (17)0.7808 (13)0.070 (15)
C180.250000.6477 (17)0.6800 (14)0.09 (2)
C190.250000.7808 (18)0.6548 (6)0.14 (3)
N0.250000.4998 (12)0.8015 (9)0.031 (7)
S0.3889 (3)0.4263 (3)0.79317 (18)0.0422 (14)
O10.3963 (10)0.3581 (8)0.7146 (5)0.063 (5)
O20.4830 (7)0.5201 (8)0.8089 (6)0.052 (5)
H40.394330.168210.792010.10000*
H60.406930.076141.050310.10000*
H70.415940.290251.085830.10000*
H1010.354830.503791.049070.10000*
H1020.354830.548430.949330.10000*
H810.352310.050620.839130.10000*
H820.352290.086190.940590.10000*
H1710.172880.675390.804980.10000*
H1810.327120.605780.656100.10000*
H1910.172880.823070.678340.10000*
H1920.250000.789450.591000.10000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (8)0.040 (7)0.036 (6)0.013 (6)0.003 (6)0.011 (6)
C20.026 (6)0.038 (7)0.046 (6)0.005 (6)0.001 (6)0.003 (5)
C30.038 (6)0.038 (6)0.034 (5)0.001 (7)0.005 (7)0.008 (5)
C40.047 (7)0.044 (7)0.043 (6)0.000 (8)0.001 (7)0.004 (6)
C50.038 (7)0.045 (8)0.063 (7)0.002 (7)0.009 (7)0.005 (6)
C60.036 (7)0.042 (7)0.057 (7)0.004 (8)0.004 (7)0.010 (6)
C70.035 (6)0.046 (7)0.036 (6)0.002 (7)0.013 (6)0.017 (6)
C80.063 (10)0.030 (6)0.089 (10)0.000 (7)0.019 (9)0.007 (8)
C170.054 (13)0.069 (16)0.087 (18)0.000000.000000.006 (16)
C180.054 (14)0.073 (19)0.15 (3)0.000000.000000.059 (19)
C190.09 (2)0.17 (4)0.16 (3)0.000000.000000.08 (3)
N0.046 (7)0.018 (7)0.028 (7)0.000000.000000.011 (7)
S0.0423 (14)0.0475 (16)0.0369 (13)0.0008 (19)0.0049 (17)0.0087 (16)
O10.084 (7)0.070 (6)0.034 (4)0.016 (6)0.007 (6)0.002 (5)
O20.037 (4)0.052 (5)0.068 (6)0.011 (4)0.006 (5)0.016 (5)
Geometric parameters (Å, º) top
C1i—H101i1.007 (8)C8i—H82i1.013 (9)
C1i—H102i1.012 (9)C8i—C8ii1.504 (18)
C1i—C2i1.512 (15)C17i—H171ii1.007 (12)
C1i—C1ii1.558 (16)C17i—H171i1.007 (12)
C2i—C7i1.398 (15)C17i—Ni1.48 (2)
C2i—C3i1.439 (15)C17i—C18i1.58 (3)
C3i—C4i1.390 (16)C18i—H181ii1.005 (12)
C3i—Si1.756 (11)C18i—H181i1.005 (12)
C4i—H4i1.011 (8)C18i—C19i1.49 (3)
C4i—C5i1.402 (16)C19i—H192i1.002 (9)
C5i—C6i1.407 (16)C19i—H191ii1.005 (9)
C5i—C8i1.532 (16)C19i—H191i1.005 (9)
C6i—H6i1.011 (11)Ni—Sii1.676 (7)
C6i—C7i1.392 (15)Ni—Si1.676 (7)
C7i—H7i1.010 (8)Si—O1i1.434 (8)
C8i—H81i1.009 (9)Si—O2i1.441 (9)
H191i···H192i1.6323 (4)H101i···H191iv3.3590 (5)
H101i···H102i1.6328 (5)C1i···C3ii3.365 (16)
H171i···H171ii1.6329 (3)C1i···C7ii3.366 (16)
H181i···H181ii1.6329 (3)C6i···H6ii3.367 (14)
H191i···H191ii1.6329 (3)C3i···H101i3.378 (11)
H81i···H82i1.6329 (5)H82i···H1813.3885 (11)
C19i···H181i2.056 (17)H82i···H1923.3926 (7)
C19i···H181ii2.056 (17)C2i···H4i3.393 (11)
C18i···H191ii2.059 (17)O1i···H191x3.394 (10)
C18i···H191i2.059 (17)C17i···H192i3.41 (2)
Ni···H171i2.062 (12)H4i···H191x3.4202 (5)
Ni···H171ii2.062 (12)C3i···Sii3.421 (13)
C2i···H101i2.065 (11)C6i···C7ii3.430 (18)
C18i···H192i2.07 (2)H81i···H191xv3.4336 (6)
C8i···H81ii2.068 (12)H101i···H101viii3.4370 (6)
C2i···H102i2.069 (11)C4i···O2xiii3.439 (14)
C8i···H82ii2.070 (12)Si···H81vi3.442 (3)
C6i···H7i2.077 (11)C1i···H101viii3.463 (11)
C2i···H7i2.079 (11)C18i···O2i3.471 (17)
C5i···H81i2.083 (12)C18i···O2ii3.471 (17)
C7i···H6i2.084 (11)C7i···H7ii3.486 (12)
C5i···H82i2.084 (12)C8i···H4ii3.490 (11)
C3i···H4i2.089 (11)C17i···O1i3.50 (2)
C5i···H4i2.103 (12)C17i···O1ii3.50 (2)
C5i···H6i2.105 (12)H7i···H7ii3.5136 (7)
C1i···H101ii2.115 (11)C18i···O1i3.527 (19)
C1i···H102ii2.117 (11)C18i···O1ii3.527 (19)
C17i···H181ii2.14 (2)C3i···H101viii3.527 (13)
C17i···H181i2.14 (2)Si···H171i3.532 (3)
C18i···H171i2.14 (2)O1i···H171x3.542 (10)
C18i···H171ii2.14 (2)C1i···H102viii3.549 (11)
H82i···H82ii2.1658 (4)C8i···H171ix3.551 (10)
H81i···H81ii2.1663 (4)H81i···H171xv3.5519 (7)
H101i···H101ii2.2196 (4)C18i···H6xvi3.563 (18)
H102i···H102ii2.2196 (4)C18i···H6v3.563 (18)
O2i···H171ii2.351 (8)C1i···H171ii3.567 (8)
H181i···H191ii2.3678 (6)H7i···H102i3.5669 (7)
H181i···H192i2.3713 (5)C8i···H6ii3.567 (11)
H6i···H7i2.3758 (6)H6i···H181xvii3.5671 (5)
O1i···H4i2.378 (8)C19i···H81xviii3.576 (12)
C3i···C7i2.380 (13)C19i···H81xix3.576 (12)
C4i···C6i2.407 (13)C5i···H4ii3.587 (13)
C3i···C5i2.411 (17)C5i···H82iii3.594 (13)
C5i···C7i2.430 (16)H4i···H81ii3.5952 (6)
H171i···H181ii2.4470 (7)C6i···C8iii3.595 (18)
C2i···C6i2.448 (15)C1i···H7ii3.600 (10)
H7i···H101i2.4591 (6)H102i···H102viii3.6127 (5)
O1i···O2i2.464 (12)C1i···H191vii3.615 (8)
Ni···O2i2.480 (8)H6i···H81i3.6216 (10)
Ni···O2ii2.480 (8)H4i···H82i3.6223 (7)
C18i···Ni2.48 (2)C1i···C2viii3.638 (16)
C2i···C4i2.485 (15)C6i···H1813.641 (11)
H4i···H81i2.5110 (6)C3i···H4ii3.649 (13)
H6i···H82i2.5184 (5)O1i···H82vi3.652 (9)
C1i···C7i2.528 (15)C4i···H81ii3.671 (13)
C17i···C19i2.53 (2)O1i···H181ii3.682 (9)
C4i···C8i2.534 (16)Si···H181ii3.684 (3)
H171i···H191i2.5414 (6)O2i···H171i3.686 (8)
C5i···C8ii2.550 (18)C17i···H81xviii3.688 (18)
C6i···C8i2.555 (14)C17i···H81xix3.688 (18)
H6i···H82iii2.5554 (5)C5i···H6ii3.689 (13)
Ni···O1i2.565 (14)C8i···O1xiii3.693 (15)
Ni···O1ii2.565 (14)C7i···O2viii3.697 (13)
C1i···C2ii2.568 (16)C1i···C19iv3.709 (17)
H101i···H192iv2.5746 (5)C4i···Ni3.712 (17)
C3i···O1i2.577 (12)Si···H4vi3.720 (3)
O1i···H7v2.580 (8)C6i···H82ii3.724 (13)
O2i···H4vi2.593 (9)C5i···C6iii3.729 (18)
C1i···C3i2.600 (14)C3i···C5ii3.729 (18)
O2i···H102i2.600 (9)C4i···O2i3.732 (15)
Ni···H102i2.619 (12)C6i···C6iii3.733 (17)
Ni···H102ii2.619 (12)C1i···C17i3.74 (2)
C3i···O2i2.626 (15)C7i···H101ii3.741 (12)
C7i···H101i2.639 (11)Si···H101viii3.744 (3)
H102i···H171ii2.6568 (6)C2i···H7ii3.746 (12)
C4i···H81i2.665 (12)C6i···H81iii3.749 (13)
O1i···H6v2.668 (7)C1i···O2viii3.752 (12)
Ni···H181i2.672 (13)C3i···H102ii3.755 (12)
Ni···H181ii2.672 (13)C3i···C8i3.761 (15)
C6i···H82i2.673 (11)C3i···H6i3.766 (11)
C17i···Si2.681 (16)C1i···C1viii3.767 (16)
C17i···Sii2.681 (16)O1i···H171ii3.772 (9)
C4i···Si2.690 (12)C1i···C6i3.774 (15)
H6i···H1812.7015 (5)C7i···H101viii3.776 (12)
H81i···H82ii2.7126 (4)C2i···C4ii3.782 (17)
C3i···Ni2.718 (16)C4i···H7i3.783 (8)
C17i···H191i2.723 (19)C7i···H4i3.786 (8)
C17i···H191ii2.723 (19)Si···H102ii3.790 (3)
C19i···H171i2.735 (11)C7i···C8i3.792 (14)
C19i···H171ii2.735 (11)C18i···H4vi3.797 (3)
C1i···H7i2.736 (9)C18i···H4xx3.797 (3)
C8i···H4i2.753 (10)C19i···Ni3.80 (2)
H101i···H102ii2.7555 (4)C8i···H191ix3.802 (8)
C3i···H102i2.756 (11)Si···H6v3.804 (3)
C3i···C6i2.757 (15)C3i···H181xiii3.816 (13)
C5i···C5ii2.76 (2)C2i···C6ii3.818 (18)
C2i···C2ii2.764 (18)C5i···C7ii3.828 (17)
H101i···H191vii2.7674 (6)C2i···H191x3.833 (12)
Si···H171ii2.770 (3)C1i···C4i3.837 (14)
C2i···Si2.771 (11)C7i···H6ii3.856 (12)
C4i···C7i2.779 (11)C8i···O2xiii3.862 (13)
C8i···H6i2.779 (9)C1i···Sii3.863 (9)
Si···H4i2.783 (3)C4i···C6ii3.863 (18)
C17i···O2i2.788 (12)C6i···H181xiii3.865 (13)
C17i···O2ii2.788 (12)C3i···C7ii3.865 (17)
Si···H102i2.798 (3)C19i···H102xi3.866 (12)
C4i···O1i2.818 (12)C19i···H102xii3.866 (12)
O2i···H101viii2.819 (9)C19i···O2xx3.869 (15)
O2i···H7viii2.834 (9)C19i···O2vi3.869 (15)
C6i···H82iii2.858 (14)C3i···H192x3.874 (14)
C2i···C5i2.862 (17)C1i···H7viii3.876 (10)
H81i···H191ix2.8726 (7)O1i···O2xiii3.878 (13)
H181i···H191i2.8763 (6)C3i···C19x3.881 (14)
O1i···H181i2.916 (9)C8i···H171xv3.882 (10)
C3i···C3ii2.93 (2)O1i···H4ii3.889 (10)
O2i···H191x2.931 (9)Ni···H4i3.890 (12)
C4i···C4ii2.94 (2)Ni···H4ii3.890 (12)
H171i···H181i2.9418 (6)C4i···C18x3.891 (15)
Si···Sii2.942 (5)C6i···H7ii3.901 (13)
O1i···H81vi2.959 (10)C2i···O1i3.906 (13)
Si···H181i2.961 (3)C1i···H171i3.907 (9)
O2i···H81vi2.997 (9)C4i···H171x3.909 (12)
C5i···H6iii3.002 (13)C4i···H6iii3.914 (12)
C17i···H102ii3.00 (2)O2i···H4i3.917 (9)
C17i···H102i3.00 (2)C5i···O2xiii3.937 (15)
H6i···H6iii3.0093 (4)C4i···C19x3.941 (15)
H81i···H171ix3.0131 (8)C1i···H191iv3.952 (9)
H171i···H191ii3.0208 (5)C17i···H4xx3.952 (6)
C1i···H192iv3.025 (9)C17i···H4vi3.952 (6)
H102i···H192iv3.0327 (6)C18i···H82xvi3.95 (2)
H7i···H102viii3.0358 (5)C18i···H82v3.95 (2)
C8i···H6iii3.048 (12)C3i···O1ii3.964 (16)
O2i···H181i3.048 (9)C2i···Sii3.976 (12)
H4i···H4ii3.0561 (6)C2i···C5ii3.978 (18)
C1i···Ni3.058 (15)C4i···Sii3.986 (14)
C19i···H101xi3.059 (15)C7i···H171xiv3.987 (11)
C19i···H101xii3.059 (15)C3i···C17i4.00 (2)
H6i···H81iii3.0927 (5)O2i···H101i3.999 (9)
O1i···O1ii3.098 (15)C1i···C7viii4.003 (16)
C6i···C6ii3.10 (2)C5i···Si4.004 (13)
H101i···H102viii3.1251 (6)Si···H7v4.007 (3)
H4i···H181xiii3.1319 (5)C6i···H101i4.008 (11)
C3i···H191x3.134 (14)C8i···H7iii4.011 (12)
C4i···H181xiii3.154 (14)C7i···Si4.014 (9)
C4i···H4ii3.164 (14)C3i···H81i4.032 (11)
C7i···C7ii3.167 (18)C2i···O2viii4.048 (14)
C2i···H101viii3.173 (12)Si···O2ii4.073 (9)
C2i···O2i3.174 (14)C3i···C6ii4.086 (18)
C4i···C5ii3.18 (2)Si···H4ii4.091 (3)
C2i···C3ii3.189 (18)C5i···O1xiii4.103 (16)
C5i···H81ii3.213 (13)C2i···C2viii4.105 (17)
C5i···H82ii3.213 (13)Si···H101i4.105 (3)
C1i···Si3.215 (8)C4i···C7ii4.127 (16)
C2i···H101ii3.225 (12)C4i···O1ii4.129 (16)
C2i···H102ii3.227 (12)C7i···C8iii4.130 (16)
H7i···H171xiv3.2334 (5)Si···H7viii4.145 (3)
Si···H191x3.236 (3)C8i···C17xv4.19 (2)
C6i···H6iii3.237 (12)C19i···Svi4.211 (8)
C3i···C4ii3.25 (2)C19i···Sxx4.211 (8)
C5i···C6ii3.25 (2)C5i···O1i4.216 (15)
C7i···O13.260 (11)C5i···C5iii4.222 (18)
H4i···H7v3.2644 (10)C5i···C18x4.232 (16)
C2i···H102viii3.267 (12)C1i···C3viii4.275 (16)
C2i···Ni3.267 (16)C1i···C5i4.290 (16)
H102i···H171i3.2685 (6)C2i···C8i4.305 (15)
C2i···C7ii3.273 (17)C3i···C8ii4.307 (16)
C4i···C8ii3.293 (17)C8i···Sxiii4.311 (11)
C3i···H7i3.296 (10)C1i···O2ii4.329 (13)
C6i···O13.301 (13)C3i···C18x4.337 (16)
C7i···H102i3.301 (11)C2i···C17i4.34 (2)
C5i···H181xiii3.307 (13)C19i···O1vi4.346 (11)
C7i···H82iii3.308 (12)C19i···O1xx4.346 (11)
C7i···H102viii3.308 (12)C5i···C8iii4.365 (17)
C18i···Sii3.316 (18)C1i···C6ii4.368 (16)
C18i···Si3.316 (18)C4i···Sxiii4.372 (12)
H4i···H171x3.3173 (5)C7i···C8ii4.376 (15)
H7i···H82iii3.3212 (5)C1i···C4ii4.394 (15)
C4i···H82i3.322 (11)C4i···O1xiii4.400 (15)
C4i···H6i3.322 (9)C8i···C19xv4.403 (15)
H6i···H6ii3.3228 (6)C2i···C19x4.413 (13)
C6i···H4i3.324 (10)C4i···C17x4.415 (17)
C1i···O2i3.324 (12)C6i···C184.43 (2)
C6i···H81i3.327 (11)C6i···Si4.512 (11)
C5i···H7i3.335 (12)C5i···Sxiii4.527 (13)
Si···O1ii3.342 (11)C6i···S4.587 (11)
H82i···H171ix3.3431 (7)C19i···Si4.632 (17)
C6i···C8ii3.346 (17)C19i···Sii4.632 (17)
C2i···H6i3.349 (11)C1i···Sviii4.661 (10)
C4i···H191x3.356 (14)C7i···S4.686 (9)
H101i—C1i—H102i108.0 (9)C8ii—C8i—C5i114.2 (9)
H101i—C1i—C2i108.5 (9)H171ii—C17i—H171i108.4 (18)
H101i—C1i—C1ii109.2 (8)H171ii—C17i—Ni110.9 (12)
H102i—C1i—C2i108.5 (8)H171ii—C17i—C18i109.3 (13)
H102i—C1i—C1ii109.1 (8)H171i—C17i—Ni110.9 (12)
C2i—C1i—C1ii113.5 (9)H171i—C17i—C18i109.3 (13)
C7i—C2i—C3i114.0 (10)Ni—C17i—C18i108.2 (15)
C7i—C2i—C1i120.6 (9)H181ii—C18i—H181i108.6 (19)
C3i—C2i—C1i123.5 (9)H181ii—C18i—C19i109.6 (13)
C4i—C3i—C2i122.9 (9)H181ii—C18i—C17i109.0 (13)
C4i—C3i—Si117.0 (7)H181i—C18i—C19i109.6 (13)
C2i—C3i—Si119.9 (8)H181i—C18i—C17i109.0 (13)
H4i—C4i—C3i120.1 (10)C19i—C18i—C17i110.9 (15)
H4i—C4i—C5i120.4 (11)H192i—C19i—H191ii108.8 (9)
C3i—C4i—C5i119.5 (9)H192i—C19i—H191i108.8 (9)
C4i—C5i—C6i117.9 (11)H192i—C19i—C18i110.7 (16)
C4i—C5i—C8i119.4 (10)H191ii—C19i—H191i108.7 (15)
C6i—C5i—C8i120.7 (10)H191ii—C19i—C18i109.9 (10)
H6i—C6i—C7i119.4 (9)H191i—C19i—C18i109.9 (10)
H6i—C6i—C5i120.1 (10)C17i—Ni—Sii116.4 (5)
C7i—C6i—C5i120.5 (10)C17i—Ni—Si116.4 (5)
H7i—C7i—C6i118.8 (9)Sii—Ni—Si122.8 (8)
H7i—C7i—C2i118.5 (10)O1i—Si—O2i118.0 (6)
C6i—C7i—C2i122.7 (8)O1i—Si—Ni110.9 (6)
H81i—C8i—H82i107.7 (10)O1i—Si—C3i107.3 (5)
H81i—C8i—C8ii109.2 (9)O2i—Si—Ni105.2 (5)
H81i—C8i—C5i108.3 (10)O2i—Si—C3i110.1 (6)
H82i—C8i—C8ii109.1 (9)Ni—Si—C3i104.7 (6)
H82i—C8i—C5i108.2 (9)
H101i—C1i—C2i—C3i160.8 (11)C6i—C5i—C8i—H82i38.1 (16)
H101i—C1i—C2i—C7i35.8 (15)C6i—C5i—C8i—C8ii83.5 (13)
H102i—C1i—C2i—C3i43.7 (15)C5i—C6i—C7i—C2i3 (2)
H102i—C1i—C2i—C7i152.9 (11)C5i—C6i—C7i—H7i176.8 (12)
C1ii—C1i—C2i—C3i77.7 (13)H6i—C6i—C7i—C2i177.2 (12)
C1ii—C1i—C2i—C7i85.7 (12)H6i—C6i—C7i—H7i3 (2)
C1i—C2i—C3i—C4i152.0 (13)Ni—C17i—C18i—C19i180.0000
C1i—C2i—C3i—Si24.5 (17)Ni—C17i—C18i—H181i59.2 (12)
C7i—C2i—C3i—C4i12 (2)Ni—C17i—C18i—H181ii59.2 (12)
C7i—C2i—C3i—Si171.1 (10)H171i—C17i—C18i—C19i59.2 (12)
C1i—C2i—C7i—C6i150.6 (12)H171i—C17i—C18i—H181i180.0 (14)
C1i—C2i—C7i—H7i29.2 (18)H171i—C17i—C18i—H181ii62 (2)
C3i—C2i—C7i—C6i14.3 (18)H171ii—C17i—C18i—C19i59.2 (12)
C3i—C2i—C7i—H7i165.9 (12)H171ii—C17i—C18i—H181i62 (2)
C2i—C3i—C4i—C5i0 (2)H171ii—C17i—C18i—H181ii180.0 (14)
C2i—C3i—C4i—H4i179.9 (13)C18i—C17i—Ni—Si78.5 (9)
Si—C3i—C4i—C5i176.0 (11)C18i—C17i—Ni—Sii78.5 (9)
Si—C3i—C4i—H4i3 (2)H171i—C17i—Ni—Si161.7 (11)
C2i—C3i—Si—Ni61.7 (12)H171i—C17i—Ni—Sii41 (2)
C2i—C3i—Si—O1i179.5 (11)H171ii—C17i—Ni—Si41 (2)
C2i—C3i—Si—O2i50.9 (12)H171ii—C17i—Ni—Sii161.7 (11)
C4i—C3i—Si—Ni115.1 (11)C17i—C18i—C19i—H191i59.8 (7)
C4i—C3i—Si—O1i2.8 (13)C17i—C18i—C19i—H192i180.0000
C4i—C3i—Si—O2i132.3 (11)C17i—C18i—C19i—H191ii59.8 (7)
C3i—C4i—C5i—C6i12 (2)H181i—C18i—C19i—H191i179.8 (13)
C3i—C4i—C5i—C8i151.8 (13)H181i—C18i—C19i—H192i59.5 (14)
H4i—C4i—C5i—C6i168.5 (13)H181i—C18i—C19i—H191ii60.7 (18)
H4i—C4i—C5i—C8i27 (2)H181ii—C18i—C19i—H191i60.7 (18)
C4i—C5i—C6i—C7i10 (2)H181ii—C18i—C19i—H192i59.5 (14)
C4i—C5i—C6i—H6i168.9 (13)H181ii—C18i—C19i—H191ii179.8 (13)
C8i—C5i—C6i—C7i153.3 (12)C17i—Ni—Si—C3i144.0 (12)
C8i—C5i—C6i—H6i27 (2)C17i—Ni—Si—O1i100.6 (12)
C4i—C5i—C8i—H81i41.9 (16)C17i—Ni—Si—O2i27.9 (13)
C4i—C5i—C8i—H82i158.3 (11)Sii—Ni—Si—C3i60.7 (10)
C4i—C5i—C8i—C8ii80.0 (13)Sii—Ni—Si—O1i54.7 (10)
C6i—C5i—C8i—H81i154.6 (12)Sii—Ni—Si—O2i176.7 (8)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1, y+1/2, z+3/2; (iv) x, y1, z; (v) x, y, z1; (vi) x+1, y, z+1; (vii) x+1/2, y1, z; (viii) x+1, y1/2, z+3/2; (ix) x+1/2, y+3/2, z1/2; (x) x+1/2, y+1, z+1; (xi) x, y1, z1; (xii) x+1/2, y1, z1; (xiii) x+1, y+1, z+1; (xiv) x+1/2, y1/2, z+3/2; (xv) x, y+3/2, z1/2; (xvi) x+1/2, y, z1; (xvii) x+1/2, y, z; (xviii) x, y1/2, z1/2; (xix) x+1/2, y1/2, z1/2; (xx) x1/2, y, z+1.
(PCF5) N-isopropyl-[2.2]paracyclophane-4,15-disulfonimide top
Crystal data top
C19H21NS2O4F(000) = 1648
Mr = 391.5Dx = 1.447 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2abCell parameters from 23 reflections
a = 12.845 (2) Åθ = 39.9–41.8°
b = 15.0121 (7) ŵ = 2.90 mm1
c = 18.6430 (8) ÅT = 293 K
V = 3594.8 (5) Å3Block, colourless
Z = 80.50 × 0.40 × 0.40 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 74.7°, θmin = 4.7°
Graphite monochromatorh = 016
θ/2θ scansk = 018
3679 measured reflectionsl = 023
3679 independent reflections2 standard reflections every 60 min
3190 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullRiding
R[F2 > 2σ(F2)] = 0.064 1/[6.9 + 0.0056*σ(Fobs)2 + 0.00004/σ(Fobs)]
wR(F2) = 0.069(Δ/σ)max = 0.258
S = 0.98Δρmax = 0.73 e Å3
3190 reflectionsΔρmin = 0.89 e Å3
320 parametersExtinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
21 restraintsExtinction coefficient: 4973 (257)
Crystal data top
C19H21NS2O4V = 3594.8 (5) Å3
Mr = 391.5Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 12.845 (2) ŵ = 2.90 mm1
b = 15.0121 (7) ÅT = 293 K
c = 18.6430 (8) Å0.50 × 0.40 × 0.40 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
3679 measured reflections2 standard reflections every 60 min
3679 independent reflections intensity decay: none
3190 reflections with refl observed if I > 2.5 σ(I )
Refinement top
R[F2 > 2σ(F2)] = 0.06421 restraints
wR(F2) = 0.069Riding
S = 0.98(Δ/σ)max = 0.258
3190 reflectionsΔρmax = 0.73 e Å3
320 parametersΔρmin = 0.89 e Å3
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2443 (4)0.2990 (4)0.8075 (3)0.051 (3)
C20.2138 (3)0.3518 (3)0.8729 (3)0.044 (2)
C30.2680 (3)0.4275 (3)0.8978 (2)0.036 (2)
C40.2661 (3)0.4523 (3)0.9693 (2)0.042 (2)
C50.2094 (4)0.4045 (3)1.0191 (3)0.050 (3)
C60.1379 (4)0.3423 (4)0.9911 (3)0.060 (3)
C70.1408 (4)0.3186 (4)0.9207 (3)0.059 (3)
C80.2391 (5)0.4032 (4)1.0966 (3)0.062 (3)
C90.3401 (4)0.2333 (3)0.8230 (3)0.049 (3)
C100.3746 (3)0.2378 (3)0.9004 (2)0.040 (2)
C110.4383 (3)0.3067 (3)0.9282 (2)0.034 (2)
C120.4354 (3)0.3299 (3)0.9996 (2)0.038 (2)
C130.3679 (3)0.2876 (3)1.0465 (2)0.044 (2)
C140.3225 (4)0.2082 (3)1.0224 (3)0.052 (3)
C150.3268 (4)0.1856 (3)0.9512 (3)0.054 (3)
C160.3302 (5)0.3337 (5)1.1127 (3)0.067 (4)
C170.4900 (3)0.4372 (3)0.7384 (2)0.044 (2)
C180.4240 (5)0.4017 (4)0.6782 (3)0.061 (3)
C190.5220 (5)0.5334 (4)0.7281 (3)0.062 (3)
N0.4415 (2)0.4190 (2)0.8115 (2)0.034 (2)
O10.2926 (2)0.5128 (2)0.7772 (2)0.052 (2)
O20.3936 (3)0.5611 (2)0.8817 (2)0.054 (2)
O40.5823 (3)0.3087 (3)0.8298 (2)0.073 (2)
O50.5732 (3)0.4347 (3)0.9153 (2)0.067 (2)
S10.34893 (7)0.49066 (7)0.84064 (5)0.0360 (5)
S20.52109 (7)0.36933 (8)0.87206 (6)0.0429 (6)
H1010.260 (4)0.333 (3)0.763 (3)0.05 (1)*
H1020.191 (3)0.266 (4)0.779 (3)0.09 (2)*
H40.310 (3)0.505 (2)0.983 (2)0.04 (1)*
H60.102 (3)0.306 (3)1.029 (2)0.06 (1)*
H70.107 (4)0.263 (2)0.904 (3)0.08 (2)*
H810.262 (4)0.465 (2)1.108 (3)0.07 (2)*
H820.193 (5)0.405 (5)1.140 (2)0.12 (3)*
H910.390 (3)0.246 (3)0.783 (2)0.05 (1)*
H920.319 (4)0.170 (1)0.816 (3)0.06 (2)*
H120.473 (3)0.386 (2)1.012 (2)0.04 (1)*
H140.284 (3)0.173 (3)1.060 (2)0.06 (2)*
H150.288 (4)0.132 (2)0.935 (3)0.09 (2)*
H1610.378 (6)0.351 (6)1.153 (4)0.18 (4)*
H1620.314 (5)0.286 (3)1.148 (3)0.10 (2)*
H170.544 (3)0.389 (2)0.745 (2)0.05 (1)*
H1810.416 (4)0.337 (1)0.690 (3)0.08 (2)*
H1820.363 (4)0.442 (4)0.683 (4)0.13 (3)*
H1830.454 (3)0.418 (3)0.631 (1)0.05 (1)*
H1910.455 (3)0.567 (4)0.731 (4)0.11 (3)*
H1920.558 (4)0.546 (4)0.774 (2)0.07 (2)*
H1930.550 (3)0.536 (3)0.678 (1)0.05 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (2)0.060 (3)0.049 (3)0.010 (2)0.024 (2)0.002 (2)
C20.023 (2)0.052 (3)0.057 (3)0.001 (2)0.013 (2)0.013 (2)
C30.021 (2)0.039 (2)0.049 (2)0.006 (2)0.004 (2)0.010 (2)
C40.033 (2)0.039 (2)0.052 (3)0.008 (2)0.012 (2)0.003 (2)
C50.041 (2)0.052 (3)0.058 (3)0.011 (2)0.020 (2)0.009 (2)
C60.034 (2)0.071 (3)0.075 (4)0.006 (2)0.013 (2)0.020 (3)
C70.030 (2)0.072 (4)0.076 (4)0.012 (2)0.009 (2)0.020 (3)
C80.075 (4)0.058 (3)0.052 (3)0.003 (3)0.030 (3)0.000 (3)
C90.063 (3)0.036 (2)0.048 (3)0.002 (2)0.014 (2)0.009 (2)
C100.041 (2)0.035 (2)0.045 (2)0.010 (2)0.008 (2)0.002 (2)
C110.025 (2)0.039 (2)0.038 (2)0.010 (2)0.005 (2)0.003 (2)
C120.029 (2)0.046 (2)0.039 (2)0.001 (2)0.009 (2)0.003 (2)
C130.038 (2)0.059 (3)0.036 (2)0.003 (2)0.007 (2)0.009 (2)
C140.050 (3)0.054 (3)0.053 (3)0.008 (2)0.010 (2)0.020 (2)
C150.061 (3)0.037 (2)0.064 (3)0.008 (2)0.021 (3)0.007 (2)
C160.070 (4)0.098 (5)0.034 (2)0.001 (3)0.004 (2)0.005 (3)
C170.036 (2)0.065 (3)0.031 (2)0.010 (2)0.004 (2)0.001 (2)
C180.071 (4)0.079 (4)0.033 (2)0.005 (3)0.001 (2)0.006 (3)
C190.056 (3)0.088 (4)0.043 (3)0.022 (3)0.010 (2)0.009 (3)
N0.025 (1)0.044 (2)0.033 (2)0.006 (1)0.000 (1)0.000 (1)
O10.042 (2)0.062 (2)0.052 (2)0.012 (2)0.004 (1)0.017 (2)
O20.055 (2)0.042 (2)0.066 (2)0.013 (2)0.020 (2)0.010 (2)
O40.047 (2)0.107 (3)0.064 (2)0.045 (2)0.017 (2)0.015 (2)
O50.046 (2)0.096 (3)0.059 (2)0.030 (2)0.019 (2)0.008 (2)
S10.0297 (5)0.0361 (5)0.0422 (5)0.0032 (4)0.0068 (4)0.0026 (4)
S20.0224 (4)0.0661 (7)0.0402 (6)0.0045 (5)0.0021 (4)0.0073 (5)
Geometric parameters (Å, º) top
C1—H1010.98 (5)C12—H121.00 (3)
C1—H1021.00 (5)C12—C131.386 (6)
C1—C21.505 (7)C13—C141.400 (7)
C1—C91.604 (7)C13—C161.496 (7)
C2—C71.388 (7)C14—H141.00 (4)
C2—C31.411 (6)C14—C151.371 (7)
C3—C41.384 (6)C15—H151.00 (4)
C3—S11.765 (4)C16—H1611.00 (7)
C4—H41.00 (3)C16—H1621.00 (5)
C4—C51.381 (7)C17—H171.00 (3)
C5—C61.410 (7)C17—C181.504 (7)
C5—C81.495 (7)C17—C191.513 (8)
C6—H61.00 (4)C17—N1.523 (5)
C6—C71.360 (8)C18—H1831.00 (3)
C7—H71.00 (4)C18—H1821.00 (5)
C8—H821.00 (5)C18—H1811.00 (2)
C8—H811.00 (3)C19—H1931.00 (2)
C8—C161.597 (9)C19—H1921.00 (4)
C9—H921.00 (2)C19—H1911.00 (4)
C9—H911.00 (3)N—S11.693 (3)
C9—C101.512 (7)N—S21.697 (3)
C10—C151.374 (7)O1—S11.426 (3)
C10—C111.416 (6)O2—S11.426 (3)
C11—C121.376 (6)O4—S21.438 (4)
C11—S21.764 (4)O5—S21.435 (4)
H161···H1621.3 (1)C1···C153.347 (7)
H101···H1021.37 (7)C19···H82x3.35 (6)
H81···H821.39 (8)C1···H162viii3.35 (5)
H182···H1831.58 (7)C6···C163.356 (8)
H191···H1921.58 (7)C1···C113.359 (6)
H91···H921.59 (5)C15···H913.36 (3)
H191···H1931.64 (6)H91···H191vi3.36 (7)
H181···H1831.71 (6)C3···C93.363 (6)
H181···H1821.73 (6)N···H1833.37 (2)
H192···H1931.80 (4)C18···H81x3.37 (5)
N···H171.86 (4)C17···H1013.38 (5)
C17···H1821.94 (6)C9···H73.38 (5)
C17···H1921.97 (5)S2···H6ix3.39 (4)
C18···H171.98 (4)C4···H823.39 (5)
C17···H1812.00 (4)C7···H153.39 (4)
C17···H1912.00 (6)C5···H1613.39 (7)
C2···H72.00 (4)C7···C93.393 (7)
C17···H1932.01 (4)C19···H91xi3.40 (5)
C5···H812.01 (5)O4···H1813.40 (6)
C10···H922.01 (4)C3···S23.401 (4)
C11···H122.02 (4)H14···H1613.40 (9)
C13···H1622.02 (5)C6···H143.40 (4)
C5···H62.02 (4)C5···H123.41 (4)
C3···H42.03 (4)C11···S13.407 (4)
C13···H142.04 (4)H92···H191vi3.41 (6)
C10···H152.04 (4)C8···H123.41 (4)
C14···H152.05 (5)H182···H1923.41 (7)
O4···H172.06 (4)O2···H92iii3.41 (4)
C6···H72.06 (5)H6···H12xii3.41 (5)
C17···H1832.08 (3)C8···C143.410 (8)
C7···H62.08 (4)C14···H181ii3.41 (5)
C1···H912.08 (4)C4···O5i3.430 (6)
H17···H1812.09 (6)S1···H173.43 (4)
C5···H42.10 (3)C8···O5i3.433 (7)
C15···H142.10 (4)C7···C143.433 (7)
C13···H122.10 (3)C3···H1023.43 (5)
C16···H822.12 (6)H101···H73.44 (7)
C9···H1012.13 (5)C13···H63.44 (4)
C9···H1022.14 (5)C18···S13.447 (5)
C2···H1012.15 (5)O1···H1923.45 (5)
H101···H912.15 (6)H181···H1933.45 (6)
C16···H812.16 (3)C3···H123.45 (4)
C1···H922.17 (3)C9···H161viii3.46 (7)
C10···H912.19 (3)H7···H17vii3.46 (6)
C2···H1022.20 (5)C10···H73.46 (5)
C19···H172.20 (3)C6···C153.460 (7)
C13···H1612.20 (7)C6···H183vii3.47 (4)
C8···H1612.21 (7)H81···H123.47 (6)
H161···H192i2.22 (9)C17···O53.467 (5)
C8···H1622.23 (5)H7···H923.47 (7)
O1···H1822.24 (7)H6···H813.48 (6)
H91···H1812.24 (6)S1···H92iii3.48 (3)
C5···H822.26 (4)C2···H183vii3.48 (4)
H102···H922.28 (6)C17···O23.483 (6)
H92···H152.32 (7)O1···H1813.49 (4)
O2···H42.32 (4)C16···H91ii3.49 (3)
H183···H1932.33 (6)C19···O1v3.491 (7)
O5···H122.33 (4)C7···H17vii3.49 (4)
C3···C72.351 (7)C18···H7v3.49 (4)
C11···C152.354 (6)C1···H153.50 (5)
C4···C62.368 (7)H102···H1813.50 (7)
C12···C142.371 (7)H91···H1823.50 (8)
H82···H1622.38 (9)C1···H1823.51 (6)
H14···H1622.39 (6)C10···H193vi3.51 (4)
H162···H181ii2.39 (6)O5···H161i3.51 (9)
H182···H1912.39 (8)C12···O2i3.521 (5)
O1···H1912.39 (5)H12···H12i3.53 (4)
C11···C132.401 (6)H6···H1623.53 (7)
C13···C152.404 (7)C3···H193vii3.54 (4)
C3···C52.409 (6)H162···H182ii3.54 (8)
C5···C72.409 (8)C16···H43.54 (4)
S2···H172.41 (5)C11···H43.54 (3)
C10···C142.412 (7)C13···H43.55 (3)
H14···H152.41 (7)H183···H1923.55 (5)
H81···H1612.41 (9)C7···H181vii3.55 (6)
C2···C62.415 (7)H91···H153.56 (6)
H17···H1922.42 (6)C15···H6ix3.56 (4)
H6···H72.42 (6)O4···H82ix3.56 (7)
H101···H1812.43 (7)H7···H161xii3.56 (9)
C10···C122.437 (6)C8···H143.57 (4)
C2···C42.441 (6)C7···C18vii3.566 (8)
O1···O22.450 (5)H162···H183ii3.57 (7)
H17···H1832.46 (5)C8···H191iv3.57 (6)
H4···H15iii2.46 (5)H181···H1913.57 (6)
N···O12.460 (4)C14···H4xiii3.58 (3)
O4···O52.476 (6)C14···C18ii3.586 (7)
N···O42.477 (5)O1···H15iii3.59 (5)
H4···H812.50 (7)H12···H1623.59 (7)
C9···C152.501 (7)C9···H192vi3.59 (5)
C12···C162.506 (7)C2···H193vii3.60 (4)
C18···N2.507 (6)C13···H6ix3.61 (4)
C4···C82.510 (7)C9···C19vi3.612 (8)
C1···C72.512 (7)H4···H823.62 (7)
H82···H1612.5 (1)C8···O1iv3.617 (6)
N···H1922.52 (5)C2···H153.62 (4)
C18···C192.521 (9)C8···H192i3.63 (4)
H17···H1932.52 (5)C15···O2xiii3.631 (6)
C6···C82.529 (8)C12···H813.63 (5)
C14···C162.529 (8)H102···H191xiii3.64 (8)
H82···H182iv2.53 (9)C14···H73.64 (5)
C19···N2.536 (7)C13···H183ii3.64 (4)
H81···H182iv2.54 (8)C19···S23.643 (6)
C15···H922.54 (5)C15···H193vi3.66 (4)
O4···H102v2.55 (5)C17···H102v3.66 (5)
C5···C162.566 (8)C6···C12xii3.670 (7)
H102···H72.57 (7)S2···H14ix3.67 (4)
H102···H912.57 (6)C1···C183.676 (8)
C8···C132.573 (7)C5···H143.68 (4)
C1···H72.58 (5)S2···H1813.69 (5)
N···O22.577 (5)C5···C113.697 (6)
C1···C102.578 (7)C12···O43.698 (5)
C1···C32.578 (7)C15···H63.70 (4)
C9···C112.579 (6)C3···C133.708 (6)
C18···H1932.58 (5)C8···H183iv3.71 (4)
C2···C92.581 (7)C4···O13.711 (5)
N···O52.582 (5)C4···H73.71 (4)
O5···H4i2.58 (4)C2···C123.714 (6)
H101···H1822.59 (8)O1···H1833.71 (3)
C3···O22.592 (5)C4···C15iii3.715 (6)
H82···H191iv2.59 (8)C3···H63.72 (4)
C4···H812.60 (5)O1···H17vii3.72 (3)
C11···O52.599 (5)C6···C11xii3.720 (7)
C19···H1822.60 (5)O4···H1923.72 (5)
N···H1812.60 (5)C14···H6ix3.72 (4)
C11···O42.605 (5)C15···H123.72 (3)
C3···O12.607 (5)C7···H43.73 (3)
C8···H62.61 (4)O2···H123.73 (3)
C14···H1622.62 (5)C16···O5i3.728 (8)
N···H1822.62 (7)C12···H153.73 (4)
H92···H193vi2.63 (6)C11···H143.73 (4)
O5···H81i2.63 (5)C11···C163.732 (7)
C19···H1832.65 (4)C7···C83.737 (8)
C9···H152.66 (5)C4···C103.737 (6)
C16···H142.67 (4)C4···N3.740 (5)
N···H1912.68 (6)S1···H1813.74 (4)
C12···S22.686 (4)C1···C63.743 (8)
C4···S12.686 (5)C3···C83.744 (7)
H102···H17vii2.69 (6)C9···C143.744 (7)
S2···H122.69 (4)C15···C163.744 (8)
C18···H1912.70 (6)C7···H923.75 (4)
S1···H42.70 (4)O5···H43.75 (4)
S1···H1912.70 (6)S2···H81i3.75 (4)
H17···H1822.71 (6)C18···O43.752 (7)
C17···S22.722 (4)C12···N3.755 (5)
N···H912.72 (5)C5···H15iii3.76 (4)
C4···C72.728 (7)C7···C12xii3.759 (7)
C12···C152.730 (7)O1···H173.77 (3)
C3···C62.731 (7)C2···C17vii3.769 (6)
C2···C102.731 (6)C9···H191vi3.77 (5)
O2···H12i2.73 (4)C7···C133.771 (7)
C5···C132.735 (7)C4···H14iii3.78 (4)
C11···C142.735 (6)O2···H102iii3.78 (5)
H101···H922.74 (6)O5···H6ix3.78 (4)
C16···H122.74 (4)C16···H92ii3.79 (5)
O2···H15iii2.74 (5)O1···H161x3.79 (8)
H91···H162viii2.75 (6)C14···H182ii3.79 (7)
C17···S12.750 (4)C2···C143.791 (7)
O1···H1012.75 (5)C3···H913.80 (4)
C3···N2.752 (5)C6···H1623.80 (6)
C11···N2.753 (5)N···H123.80 (4)
C8···H42.77 (4)O1···H1933.80 (4)
O4···H912.78 (4)C9···C123.800 (6)
C2···S12.778 (4)O1···H102iii3.80 (5)
C10···S22.778 (4)C9···H173.80 (3)
H182···H1932.79 (7)C1···C43.804 (7)
H4···H122.81 (5)C17···H101v3.81 (5)
H6···H822.81 (7)C17···H82x3.81 (6)
N···H1012.82 (5)O2···O5i3.810 (5)
C11···H6ix2.82 (4)C6···C103.816 (7)
C10···C132.826 (6)C9···O1xiii3.819 (6)
C4···O22.832 (5)C13···C18ii3.824 (8)
C17···O42.836 (6)C7···C113.828 (6)
C18···H1012.84 (5)C6···C123.830 (6)
C7···H1022.84 (5)N···H43.83 (4)
C2···C52.839 (7)C5···C153.831 (7)
C12···O52.842 (6)O4···H191vi3.84 (6)
O1···H82x2.84 (5)O1···H43.84 (4)
O1···H92iii2.85 (3)C3···C153.841 (6)
H91···H161viii2.85 (8)C15···H1023.85 (5)
C4···H15iii2.86 (4)C6···H153.85 (4)
H101···H162viii2.87 (7)C19···O53.848 (7)
C17···O12.871 (5)C16···H7ix3.85 (5)
H81···H1622.88 (5)C9···C183.852 (8)
C3···H1012.89 (5)C11···H1013.85 (5)
O4···H101v2.89 (5)O4···H123.85 (4)
C3···C112.898 (5)C7···H143.85 (4)
H14···H183ii2.90 (6)C18···S23.854 (5)
C4···C122.903 (6)S1···H913.85 (5)
H17···H1912.91 (7)C16···H101ii3.86 (5)
H101···H17vii2.91 (6)C4···C143.865 (7)
O2···H1912.91 (7)C16···H102ii3.87 (5)
C11···H912.91 (3)C18···H161viii3.88 (9)
H183···H1912.92 (7)C12···O5i3.876 (6)
O2···H1922.92 (4)C9···S13.879 (5)
S1···S22.924 (1)C11···H173.88 (4)
H12···H1612.94 (8)C16···O2i3.884 (7)
H161···H181ii2.95 (9)C5···O5i3.888 (6)
C4···H122.95 (4)S2···H102v3.89 (5)
H92···H192vi2.96 (6)C14···H923.90 (5)
H14···H181ii2.96 (7)C7···C13xii3.899 (7)
C12···H1612.97 (7)C1···S23.899 (5)
C7···H183vii2.98 (4)C2···O23.903 (5)
S2···H912.99 (4)S1···H123.91 (4)
H102···H162viii3.00 (7)C8···C18iv3.908 (9)
H91···H173.00 (5)C10···O53.914 (6)
S1···H1013.00 (5)C2···C133.915 (6)
C18···O13.005 (7)C2···C18vii3.915 (7)
C19···H92xi3.01 (4)S1···H193vii3.92 (4)
C12···H6ix3.01 (4)C7···H193vii3.92 (4)
C6···H823.02 (5)C14···H7ix3.93 (5)
S1···H1823.03 (7)C16···C18ii3.93 (1)
O2···O53.053 (5)O1···H1023.93 (5)
O2···H7iii3.05 (3)C3···O53.936 (5)
H14···H182ii3.06 (8)C5···H182iv3.94 (7)
C18···H14viii3.06 (4)C4···S23.945 (4)
C1···H17vii3.07 (3)C9···C173.946 (7)
S1···H1923.07 (5)C19···O43.948 (8)
O5···H12i3.08 (3)C11···H7ix3.95 (5)
C18···H913.08 (4)S2···H4i3.95 (4)
C9···N3.085 (6)C7···H12xii3.95 (3)
C9···H1813.09 (5)C2···S23.956 (4)
C12···H43.09 (3)C5···C103.957 (6)
H7···H153.10 (6)C7···O2xiii3.958 (7)
C19···H161i3.10 (8)C11···O23.959 (5)
C19···O13.101 (7)S2···H1013.96 (5)
C1···N3.109 (6)C3···H17vii3.96 (4)
C8···H182iv3.11 (6)S2···H43.96 (4)
H7···H183vii3.11 (6)C1···C17vii3.962 (7)
O5···H1923.12 (4)C7···C17vii3.965 (7)
C19···S13.123 (6)C3···H813.97 (5)
C16···H192i3.12 (4)C10···S13.970 (4)
H6···H143.13 (6)C15···H1623.97 (5)
C5···C123.133 (6)O5···H82i3.98 (6)
C2···C113.136 (5)C5···H183iv3.98 (4)
C16···H181ii3.14 (4)C12···S13.980 (4)
C4···C133.146 (6)C16···O4xii3.982 (8)
C2···H17vii3.15 (4)O4···H923.98 (4)
H92···H161viii3.15 (8)C1···C173.991 (7)
H4···H14iii3.16 (5)C5···S13.994 (5)
C10···O43.159 (6)C13···S23.995 (4)
C3···C103.161 (6)N···H1024.00 (5)
O4···H6ix3.16 (4)C15···S24.002 (5)
C6···C143.164 (7)C2···H181vii4.00 (6)
C7···C153.165 (7)C4···H1614.00 (7)
C12···H7ix3.17 (5)C8···O4xii4.006 (7)
C1···H1813.17 (6)C7···S14.006 (5)
C2···O13.170 (6)S2···H101v4.01 (5)
C15···H73.18 (5)C17···H7v4.02 (4)
H81···H192i3.19 (7)S1···H12i4.02 (4)
C14···H63.19 (4)C6···H12xii4.02 (3)
H92···H162viii3.19 (7)C14···O5xii4.025 (6)
O5···H14ix3.19 (4)S1···H1934.03 (3)
C18···H162viii3.20 (5)C14···H824.04 (6)
O1···H192vii3.20 (5)C15···H183ii4.04 (3)
C4···C113.203 (6)C6···C13xii4.040 (7)
H7···H181vii3.21 (7)C13···O2i4.042 (6)
C13···H813.21 (4)S2···H1914.05 (6)
H7···H12xii3.22 (5)O1···S24.048 (3)
C3···C123.222 (6)C16···C19i4.048 (8)
C3···H15iii3.22 (4)C9···C16viii4.048 (7)
C9···S23.227 (5)C17···O1v4.059 (5)
H4···H12i3.23 (5)O4···S14.061 (4)
C2···H923.23 (3)C7···C124.064 (6)
C2···H913.23 (4)C6···C114.068 (6)
C3···H73.23 (4)C4···O54.080 (5)
C4···H63.23 (4)C3···C144.090 (7)
C1···S13.235 (5)S1···H82x4.09 (5)
C6···C133.235 (7)C4···C154.094 (6)
C2···C153.236 (7)C6···O4xii4.097 (7)
O1···H81x3.24 (5)C11···C174.100 (6)
C12···H143.25 (4)S2···H924.10 (4)
O1···H193vii3.25 (4)S1···H1024.10 (5)
C14···H183ii3.25 (4)C9···O2xiii4.109 (6)
C17···H913.25 (4)C10···C19vi4.113 (8)
C12···H1623.25 (5)C6···C10xii4.120 (7)
S2···H1923.25 (5)C3···C174.122 (6)
C7···C103.261 (6)C4···C14iii4.127 (7)
C11···H153.26 (4)C2···C19vii4.128 (8)
S1···H15iii3.26 (5)C6···C14xii4.129 (7)
H82···H183iv3.26 (8)C14···O4xii4.143 (6)
H91···H192vi3.27 (7)C12···O24.144 (5)
C6···H813.27 (5)C16···O1iv4.146 (7)
O5···H173.27 (5)C6···C15xii4.159 (7)
C10···H1013.27 (5)O5···O5i4.167 (5)
C10···H6ix3.28 (4)C3···C15iii4.181 (6)
O2···H161i3.28 (8)C2···O4vii4.190 (6)
C5···H1623.28 (5)C5···O24.206 (6)
H161···H191i3.29 (9)S2···H1824.21 (7)
C5···C143.285 (7)C1···O2xiii4.220 (6)
C9···H193vi3.29 (5)C13···O54.221 (6)
C9···H162viii3.29 (5)C15···S1xiii4.231 (5)
C15···H4xiii3.29 (3)S1···H161i4.24 (8)
C10···H1023.29 (5)C7···C14xii4.243 (7)
C8···C123.294 (7)C3···C19vii4.245 (7)
C13···H7ix3.29 (5)C10···C164.251 (7)
H15···H193vi3.30 (6)C2···C84.255 (7)
C18···H1923.30 (5)C8···C19iv4.261 (8)
C13···H153.30 (5)C9···C134.261 (6)
C2···N3.299 (5)S2···H12i4.26 (3)
C6···H43.30 (3)C7···C11xii4.271 (7)
C10···H123.30 (3)C1···C54.274 (7)
C10···N3.300 (5)C6···C18vii4.280 (8)
C5···H73.30 (4)S1···H1834.28 (3)
C14···H123.30 (3)C1···C16viii4.286 (8)
C1···O4vii3.302 (6)S1···H7iii4.29 (3)
H81···H14iii3.31 (5)C13···O5i4.297 (6)
O5···S13.308 (4)C8···C114.302 (7)
H81···H183iv3.31 (6)C3···C164.323 (7)
C2···H63.31 (4)C9···O14.326 (6)
C11···H923.31 (4)C7···C164.335 (8)
C9···O43.314 (6)C6···S2xii4.342 (6)
C7···H1013.32 (5)C1···C144.350 (7)
C2···H43.32 (4)C1···O1xiii4.359 (6)
C4···C163.317 (7)C10···O2xiii4.362 (5)
O2···S23.317 (3)C1···O44.364 (6)
C1···O13.318 (6)C1···C124.367 (6)
C13···H181ii3.32 (5)C4···C94.377 (6)
O4···H162ix3.32 (6)C3···C17vii4.383 (6)
C14···H1613.32 (8)C6···C94.387 (7)
H82···H193iv3.32 (7)C9···S1xiii4.390 (5)
C19···H1813.33 (3)C8···C154.392 (8)
O4···H14ix3.33 (4)C15···O44.394 (6)
C10···H143.33 (4)C1···C18vii4.402 (8)
C19···O23.330 (6)C5···C15iii4.430 (7)
H91···H193vi3.33 (6)C19···S1v4.437 (6)
N···H1933.34 (3)C6···S14.492 (6)
C18···H82x3.34 (7)C14···S2xii4.496 (5)
C13···H823.34 (6)C14···S24.496 (5)
H162···H192i3.35 (7)C1···S2vii4.532 (5)
C16···H63.35 (4)C8···S2i4.636 (6)
H101—C1—H10287 (4)C14—C13—C16121.6 (4)
H101—C1—C2117 (3)H14—C14—C15124 (2)
H101—C1—C9108 (3)H14—C14—C13115 (2)
H102—C1—C2121 (3)C15—C14—C13120.3 (5)
H102—C1—C9108 (3)H15—C15—C14119 (3)
C2—C1—C9112.2 (4)H15—C15—C10118 (3)
C7—C2—C3114.3 (4)C14—C15—C10122.9 (5)
C7—C2—C1120.5 (4)H161—C16—H16280 (6)
C3—C2—C1124.2 (4)H161—C16—C13123 (4)
C4—C3—C2121.7 (4)H161—C16—C8115 (5)
C4—C3—S1116.6 (3)H162—C16—C13106 (3)
C2—C3—S1121.6 (3)H162—C16—C8116 (3)
H4—C4—C5123 (2)C13—C16—C8112.6 (4)
H4—C4—C3116 (2)H17—C17—C18103 (2)
C5—C4—C3121.1 (4)H17—C17—C19121 (2)
C4—C5—C6116.0 (5)H17—C17—N93 (3)
C4—C5—C8121.5 (4)C18—C17—C19113.4 (4)
C6—C5—C8121.0 (5)C18—C17—N111.9 (4)
H6—C6—C7123 (2)C19—C17—N113.3 (4)
H6—C6—C5113 (2)H183—C18—H182104 (5)
C7—C6—C5120.8 (5)H183—C18—H181118 (4)
H7—C7—C6121 (3)H183—C18—C17111 (2)
H7—C7—C2113 (3)H182—C18—H181120 (5)
C6—C7—C2123.0 (5)H182—C18—C1799 (4)
H82—C8—H8188 (5)H181—C18—C17104 (3)
H82—C8—C5129 (3)H193—C19—H192129 (4)
H82—C8—C16107 (4)H193—C19—H191111 (5)
H81—C8—C5106 (3)H193—C19—C17104 (3)
H81—C8—C16111 (3)H192—C19—H191105 (5)
C5—C8—C16112.2 (4)H192—C19—C17101 (3)
H92—C9—H91105 (4)H191—C19—C17104 (3)
H92—C9—C10105 (3)C17—N—S1117.4 (3)
H92—C9—C1111 (3)C17—N—S2115.4 (2)
H91—C9—C10120 (2)S1—N—S2119.2 (2)
H91—C9—C1104 (2)O2—S1—O1118.4 (2)
C10—C9—C1111.7 (4)O2—S1—N111.1 (2)
C15—C10—C11115.0 (4)O2—S1—C3108.2 (2)
C15—C10—C9120.1 (4)O1—S1—N103.8 (2)
C11—C10—C9123.4 (4)O1—S1—C3109.1 (2)
C12—C11—C10121.5 (4)N—S1—C3105.5 (2)
C12—C11—S2117.0 (3)O5—S2—O4119.0 (2)
C10—C11—S2121.4 (3)O5—S2—N110.8 (2)
H12—C12—C11115 (2)O5—S2—C11108.2 (2)
H12—C12—C13123 (2)O4—S2—N104.1 (2)
C11—C12—C13120.7 (4)O4—S2—C11108.5 (2)
C12—C13—C14116.6 (4)N—S2—C11105.4 (2)
C12—C13—C16120.8 (5)
C9—C1—C2—C378.4 (6)C15—C10—C11—S2170.2 (3)
C9—C1—C2—C789.3 (5)C9—C10—C15—C14153.7 (5)
H101—C1—C2—C348 (3)C9—C10—C15—H1520 (3)
H101—C1—C2—C7145 (3)C11—C10—C15—C1413.0 (7)
H102—C1—C2—C3152 (4)C11—C10—C15—H15173 (3)
H102—C1—C2—C740 (4)C10—C11—C12—C131.6 (6)
C2—C1—C9—C101.9 (6)C10—C11—C12—H12170 (2)
C2—C1—C9—H91129 (2)S2—C11—C12—C13176.1 (3)
C2—C1—C9—H92118 (3)S2—C11—C12—H128 (2)
H101—C1—C9—C10133 (3)C10—C11—S2—N60.2 (4)
H101—C1—C9—H912 (4)C10—C11—S2—O450.8 (4)
H101—C1—C9—H92111 (4)C10—C11—S2—O5178.8 (3)
H102—C1—C9—C10134 (3)C12—C11—S2—N117.5 (3)
H102—C1—C9—H9194 (4)C12—C11—S2—O4131.5 (3)
H102—C1—C9—H9218 (4)C12—C11—S2—O51.1 (4)
C1—C2—C3—C4153.6 (4)C11—C12—C13—C1414.8 (6)
C1—C2—C3—S121.8 (6)C11—C12—C13—C16153.8 (4)
C7—C2—C3—C414.8 (6)H12—C12—C13—C14178 (2)
C7—C2—C3—S1169.9 (3)H12—C12—C13—C1613 (2)
C1—C2—C7—C6154.0 (5)C12—C13—C14—C1514.2 (7)
C1—C2—C7—H77 (3)C12—C13—C14—H14170 (3)
C3—C2—C7—C614.8 (7)C16—C13—C14—C15154.3 (5)
C3—C2—C7—H7176 (3)C16—C13—C14—H1422 (3)
C2—C3—C4—C51.1 (6)C12—C13—C16—C878.7 (6)
C2—C3—C4—H4176 (2)C12—C13—C16—H16165 (6)
S1—C3—C4—C5176.7 (3)C12—C13—C16—H162153 (4)
S1—C3—C4—H40 (2)C14—C13—C16—C889.2 (6)
C2—C3—S1—N60.0 (4)C14—C13—C16—H161128 (6)
C2—C3—S1—O151.0 (4)C14—C13—C16—H16239 (4)
C2—C3—S1—O2179.0 (3)C13—C14—C15—C100.0 (8)
C4—C3—S1—N115.6 (3)C13—C14—C15—H15174 (3)
C4—C3—S1—O1133.4 (3)H14—C14—C15—C10176 (3)
C4—C3—S1—O23.4 (4)H14—C14—C15—H152 (4)
C3—C4—C5—C612.9 (7)C19—C17—C18—H181174 (3)
C3—C4—C5—C8153.5 (5)C19—C17—C18—H18263 (4)
H4—C4—C5—C6170 (2)C19—C17—C18—H18346 (3)
H4—C4—C5—C824 (2)N—C17—C18—H18157 (3)
C4—C5—C6—C713.0 (7)N—C17—C18—H18267 (4)
C4—C5—C6—H6176 (3)N—C17—C18—H183176 (3)
C8—C5—C6—C7153.5 (5)H17—C17—C18—H18142 (4)
C8—C5—C6—H610 (3)H17—C17—C18—H182165 (4)
C4—C5—C8—C1681.5 (6)H17—C17—C18—H18386 (4)
C4—C5—C8—H8139 (3)C18—C17—C19—H19166 (4)
C4—C5—C8—H82140 (6)C18—C17—C19—H192175 (3)
C6—C5—C8—C1684.3 (6)C18—C17—C19—H19349 (3)
C6—C5—C8—H81155 (3)N—C17—C19—H19162 (4)
C6—C5—C8—H8254 (6)N—C17—C19—H19246 (3)
C5—C6—C7—C21.2 (8)N—C17—C19—H193178 (3)
C5—C6—C7—H7161 (3)H17—C17—C19—H191171 (5)
H6—C6—C7—C2160 (3)H17—C17—C19—H19262 (4)
H6—C6—C7—H70 (4)H17—C17—C19—H19373 (4)
C5—C8—C16—C131.8 (7)C18—C17—N—S182.8 (5)
C5—C8—C16—H161148 (5)C18—C17—N—S2128.4 (4)
C5—C8—C16—H162121 (3)C19—C17—N—S146.9 (5)
H81—C8—C16—C13116 (3)C19—C17—N—S2101.9 (4)
H81—C8—C16—H16130 (6)H17—C17—N—S1172 (2)
H81—C8—C16—H162121 (5)H17—C17—N—S223 (2)
H82—C8—C16—C13149 (4)C17—N—S1—C3151.9 (3)
H82—C8—C16—H16164 (6)C17—N—S1—O137.2 (3)
H82—C8—C16—H16226 (5)C17—N—S1—O291.1 (3)
C1—C9—C10—C1179.3 (5)S2—N—S1—C360.5 (3)
C1—C9—C10—C1586.2 (5)S2—N—S1—O1175.2 (2)
H91—C9—C10—C1143 (3)S2—N—S1—O256.5 (3)
H91—C9—C10—C15152 (3)C17—N—S2—C11150.6 (3)
H92—C9—C10—C11161 (3)C17—N—S2—O436.5 (3)
H92—C9—C10—C1534 (3)C17—N—S2—O592.5 (3)
C9—C10—C11—C12154.0 (4)S1—N—S2—C1161.2 (3)
C9—C10—C11—S223.6 (6)S1—N—S2—O4175.3 (2)
C15—C10—C11—C1212.2 (6)S1—N—S2—O555.7 (3)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y+1, z+1/2; (v) x+1/2, y, z+3/2; (vi) x+1, y1/2, z+3/2; (vii) x1/2, y, z+3/2; (viii) x, y+1/2, z1/2; (ix) x+1/2, y+1/2, z+2; (x) x+1/2, y+1, z1/2; (xi) x+1, y+1/2, z+3/2; (xii) x1/2, y+1/2, z+2; (xiii) x+1/2, y1/2, z.
(PCF6) N-cyclopropyl-[2.2]paracyclophane-4,15-disulfonimide top
Crystal data top
C19H19NS2O4F(000) = 1632
Mr = 389.5Dx = 1.51 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 23 reflections
a = 9.826 (2) Åθ = 20.0–20.9°
b = 14.632 (2) ŵ = 0.34 mm1
c = 23.770 (4) ÅT = 293 K
V = 3418 (1) Å3Block, colourless
Z = 80.50 × 0.45 × 0.40 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 29.9°, θmin = 1.7°
Graphite monochromatorh = 013
θ/2θ scansk = 020
4940 measured reflectionsl = 033
4940 independent reflections2 standard reflections every 60 min
3089 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullRiding
R[F2 > 2σ(F2)] = 0.046 1/[6.2 + 0.0085*σ(Fobs)2 + 0.00009/σ(Fobs)]
wR(F2) = 0.052(Δ/σ)max = 0.205
S = 0.77Δρmax = 0.29 e Å3
3089 reflectionsΔρmin = 0.39 e Å3
312 parametersExtinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
19 restraintsExtinction coefficient: 17781 (506)
Crystal data top
C19H19NS2O4V = 3418 (1) Å3
Mr = 389.5Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.826 (2) ŵ = 0.34 mm1
b = 14.632 (2) ÅT = 293 K
c = 23.770 (4) Å0.50 × 0.45 × 0.40 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
4940 measured reflections2 standard reflections every 60 min
4940 independent reflections intensity decay: none
3089 reflections with refl observed if I > 2.5 σ(I )
Refinement top
R[F2 > 2σ(F2)] = 0.04619 restraints
wR(F2) = 0.052Riding
S = 0.77(Δ/σ)max = 0.205
3089 reflectionsΔρmax = 0.29 e Å3
312 parametersΔρmin = 0.39 e Å3
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5051 (4)0.2877 (3)0.6928 (2)0.043 (2)
C20.5296 (3)0.2754 (2)0.6314 (1)0.033 (2)
C30.4832 (3)0.3369 (2)0.5898 (1)0.029 (1)
C40.5486 (3)0.3466 (2)0.5381 (1)0.032 (2)
C50.6651 (3)0.2953 (2)0.5261 (1)0.036 (2)
C60.6911 (4)0.2215 (2)0.5608 (2)0.042 (2)
C70.6246 (4)0.2114 (2)0.6119 (2)0.042 (2)
C80.7694 (4)0.3311 (3)0.4849 (2)0.049 (2)
C90.6021 (4)0.3628 (3)0.7199 (2)0.042 (2)
C100.7053 (3)0.3985 (2)0.6789 (1)0.037 (2)
C110.6772 (3)0.4658 (2)0.6373 (1)0.033 (2)
C120.7485 (3)0.4716 (2)0.5873 (1)0.036 (2)
C130.8515 (3)0.4093 (3)0.5756 (2)0.043 (2)
C140.8982 (4)0.3552 (3)0.6196 (2)0.051 (2)
C150.8265 (4)0.3498 (3)0.6696 (2)0.048 (2)
C160.8858 (4)0.3876 (3)0.5150 (2)0.053 (2)
C170.2930 (4)0.5214 (2)0.6890 (1)0.037 (2)
C180.1581 (4)0.5521 (3)0.6663 (2)0.052 (2)
C190.2567 (5)0.6209 (3)0.6865 (2)0.056 (3)
N0.3981 (3)0.4842 (2)0.6512 (1)0.033 (1)
O10.3121 (3)0.4557 (2)0.5512 (1)0.052 (2)
O20.2377 (2)0.3587 (2)0.6299 (1)0.052 (2)
O40.5368 (3)0.6014 (2)0.5969 (1)0.046 (1)
O50.5569 (3)0.5886 (2)0.7002 (1)0.051 (2)
S10.34359 (8)0.40874 (5)0.60215 (4)0.0340 (4)
S20.54288 (8)0.54553 (5)0.64612 (4)0.0334 (4)
H1010.520 (4)0.230 (2)0.714 (2)0.07 (1)*
H1020.411 (2)0.308 (3)0.702 (2)0.07 (1)*
H40.523 (3)0.395 (2)0.511 (1)0.029 (9)*
H60.770 (2)0.182 (2)0.550 (1)0.033 (9)*
H70.659 (3)0.168 (2)0.641 (1)0.035 (9)*
H810.809 (3)0.281 (2)0.462 (1)0.05 (1)*
H820.720 (4)0.369 (2)0.457 (1)0.06 (1)*
H910.645 (4)0.337 (3)0.754 (1)0.08 (2)*
H920.541 (4)0.413 (2)0.732 (2)0.07 (1)*
H120.718 (4)0.518 (2)0.560 (1)0.05 (1)*
H140.975 (3)0.313 (2)0.611 (2)0.05 (1)*
H150.857 (4)0.309 (2)0.700 (1)0.07 (1)*
H1610.971 (3)0.351 (3)0.514 (2)0.09 (2)*
H1620.899 (4)0.449 (2)0.497 (2)0.07 (1)*
H170.299 (4)0.495 (2)0.7276 (7)0.04 (1)*
H1810.146 (4)0.550 (3)0.6241 (5)0.05 (1)*
H1820.081 (3)0.534 (2)0.691 (1)0.05 (1)*
H1910.243 (5)0.645 (3)0.7255 (8)0.07 (1)*
H1920.302 (3)0.659 (2)0.657 (1)0.05 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (2)0.038 (2)0.046 (2)0.008 (2)0.000 (2)0.008 (2)
C20.030 (2)0.027 (1)0.043 (2)0.005 (1)0.006 (1)0.001 (1)
C30.024 (1)0.023 (1)0.040 (2)0.000 (1)0.004 (1)0.006 (1)
C40.034 (2)0.028 (1)0.033 (2)0.003 (1)0.004 (1)0.006 (1)
C50.036 (2)0.030 (1)0.041 (2)0.007 (1)0.002 (1)0.010 (1)
C60.038 (2)0.031 (2)0.056 (2)0.011 (1)0.002 (2)0.010 (2)
C70.042 (2)0.025 (1)0.058 (3)0.003 (1)0.013 (2)0.003 (1)
C80.051 (2)0.047 (2)0.049 (2)0.010 (2)0.017 (2)0.007 (2)
C90.053 (2)0.043 (2)0.030 (2)0.008 (2)0.004 (2)0.001 (1)
C100.038 (2)0.039 (2)0.034 (2)0.009 (1)0.013 (1)0.002 (1)
C110.027 (1)0.032 (2)0.040 (2)0.007 (1)0.002 (1)0.005 (1)
C120.030 (1)0.031 (2)0.047 (2)0.004 (1)0.004 (1)0.000 (1)
C130.027 (1)0.046 (2)0.055 (2)0.004 (2)0.004 (1)0.001 (2)
C140.027 (2)0.055 (2)0.071 (3)0.004 (2)0.010 (2)0.009 (2)
C150.041 (2)0.051 (2)0.053 (2)0.000 (2)0.021 (2)0.004 (2)
C160.037 (2)0.057 (3)0.066 (3)0.007 (2)0.017 (2)0.001 (2)
C170.043 (2)0.037 (2)0.033 (2)0.005 (1)0.014 (1)0.001 (1)
C180.042 (2)0.055 (2)0.059 (3)0.014 (2)0.015 (2)0.006 (2)
C190.065 (3)0.039 (2)0.066 (3)0.013 (2)0.024 (2)0.001 (2)
N0.029 (1)0.030 (1)0.042 (2)0.003 (1)0.008 (1)0.006 (1)
O10.050 (2)0.051 (2)0.054 (2)0.022 (1)0.014 (1)0.005 (1)
O20.028 (1)0.044 (1)0.085 (2)0.009 (1)0.008 (1)0.012 (1)
O40.044 (1)0.038 (1)0.056 (2)0.001 (1)0.008 (1)0.013 (1)
O50.057 (2)0.044 (1)0.052 (2)0.004 (1)0.002 (1)0.020 (1)
S10.0246 (3)0.0315 (4)0.0458 (5)0.0021 (3)0.0028 (3)0.0067 (3)
S20.0339 (4)0.0267 (3)0.0398 (4)0.0050 (3)0.0030 (4)0.0035 (3)
Geometric parameters (Å, º) top
C1—H1011.00 (3)C12—H120.99 (3)
C1—H1021.00 (2)C12—C131.390 (5)
C1—C21.491 (5)C13—C141.389 (6)
C1—C91.592 (6)C13—C161.515 (6)
C2—C71.401 (5)C14—H141.00 (3)
C2—C31.412 (4)C14—C151.384 (6)
C3—C41.395 (5)C15—H151.00 (3)
C3—S11.753 (3)C16—H1621.00 (3)
C4—H40.99 (2)C16—H1611.00 (3)
C4—C51.397 (5)C17—H171.00 (2)
C5—C61.383 (5)C17—N1.473 (4)
C5—C81.512 (5)C17—C181.500 (6)
C6—H61.00 (2)C17—C191.501 (5)
C6—C71.387 (6)C18—H1821.00 (3)
C7—H71.00 (3)C18—H1811.01 (1)
C8—H821.00 (3)C18—C191.478 (6)
C8—H811.00 (3)C19—H1911.00 (2)
C8—C161.582 (6)C19—H1921.00 (3)
C9—H921.00 (3)N—S21.686 (3)
C9—H911.00 (3)N—S11.693 (3)
C9—C101.501 (5)O1—S11.426 (3)
C10—C151.405 (5)O2—S11.433 (3)
C10—C111.421 (5)O4—S21.428 (3)
C11—C121.382 (5)O5—S21.438 (3)
C11—S21.774 (3)
H81···H821.56 (5)C18···O5i3.369 (5)
H101···H1021.60 (5)C1···C113.375 (5)
H91···H921.61 (5)C11···H7iv3.38 (3)
H161···H1621.65 (5)C11···H913.38 (3)
H181···H1821.74 (4)H91···H192xi3.38 (5)
H191···H1921.74 (4)C3···S23.385 (3)
C13···H1622.01 (4)H4···H81viii3.39 (4)
C5···H62.03 (3)C16···O1vi3.393 (5)
C2···H72.03 (3)C7···C93.399 (5)
C11···H122.03 (3)C5···H123.40 (3)
C13···H142.04 (3)O4···S13.401 (3)
C5···H822.05 (3)C4···O4vi3.403 (4)
C5···H42.06 (3)C4···C163.411 (5)
C10···H152.06 (4)C19···H82vi3.41 (3)
C13···H1612.06 (4)C7···H153.42 (4)
C17···H1912.06 (4)C17···O13.419 (4)
C10···H922.06 (4)C7···C143.419 (5)
N···H172.07 (2)H17···H182v3.43 (4)
C14···H152.08 (3)C18···O13.429 (5)
C2···H1012.08 (4)H14···H1623.44 (5)
C15···H142.09 (3)S2···H7iv3.44 (3)
C6···H72.09 (3)C16···H181vi3.44 (2)
C9···H1022.09 (3)C8···H192vi3.45 (3)
C17···H1822.09 (3)C17···O43.449 (4)
C2···H1022.09 (4)C7···H12ii3.45 (3)
C5···H812.10 (3)C9···H73.45 (3)
C3···H42.10 (3)C11···H17v3.45 (2)
C1···H922.10 (3)O1···S23.458 (3)
C7···H62.10 (3)C6···C153.460 (6)
C10···H912.10 (3)C8···C143.461 (6)
C13···H122.10 (3)C12···H823.46 (3)
C19···H1812.11 (3)C4···H6viii3.47 (3)
C9···H1012.11 (3)C13···H63.47 (3)
C18···H1922.12 (3)O1···H81viii3.48 (3)
C8···H1612.12 (3)H4···H813.48 (4)
C18···H1912.12 (4)H7···H181ix3.48 (5)
C19···H172.12 (3)C1···H153.48 (4)
H102···H922.13 (5)C7···H161viii3.48 (5)
C1···H912.14 (4)C17···H92i3.48 (4)
C16···H812.15 (3)C11···S13.485 (3)
C19···H1822.15 (3)H102···H73.49 (4)
C17···H1922.15 (3)C19···O43.492 (6)
C17···H1812.16 (3)C12···O1vi3.511 (5)
C16···H822.16 (3)C10···H73.52 (3)
C8···H1622.16 (3)C6···H1613.52 (4)
C18···H172.17 (3)C11···H43.52 (3)
H101···H912.21 (5)H101···H153.53 (6)
H17···H1912.25 (5)N···H82vi3.54 (3)
H81···H1612.27 (5)C1···C19ix3.549 (6)
H82···H1622.32 (5)H92···H153.55 (5)
O4···H122.33 (3)H6···H823.55 (4)
H181···H1922.34 (5)S2···H6iv3.56 (3)
H4···H822.36 (5)C9···H173.56 (3)
C3···C72.362 (4)C7···H81viii3.56 (3)
H14···H1612.36 (6)C7···H181ix3.56 (4)
C4···C62.367 (5)C16···H43.57 (3)
C11···C152.370 (5)C13···H43.58 (3)
H17···H1822.37 (4)C19···H91x3.58 (4)
C12···C142.377 (5)C3···H123.59 (3)
H101···H72.38 (5)S1···H82vi3.59 (3)
H102···H15i2.39 (5)C18···H7xii3.60 (3)
C11···C132.401 (5)C19···H101x3.60 (4)
H182···H1912.41 (5)H101···H192ix3.60 (5)
C13···C152.409 (6)C14···H182xiii3.61 (3)
C5···C72.414 (5)C3···H923.61 (4)
H6···H12ii2.42 (4)C15···H91v3.62 (4)
H14···H152.42 (5)H91···H14i3.62 (5)
C3···C52.419 (5)C8···H143.63 (3)
C2···C62.440 (5)C5···C113.636 (5)
H6···H72.44 (4)C15···H1013.64 (4)
C10···C142.445 (5)O4···H43.65 (2)
O1···H42.45 (3)C17···O5i3.645 (4)
C2···C42.458 (5)C14···H73.65 (3)
O1···O22.459 (4)C13···H162iii3.65 (4)
C10···C122.461 (5)C2···H153.65 (4)
O4···O52.469 (4)C9···H102v3.65 (3)
N···O22.473 (4)S1···H923.65 (4)
N···O52.474 (4)C1···H192ix3.66 (3)
H91···H152.48 (6)C5···H143.66 (3)
H162···H162iii2.49 (5)C4···N3.671 (4)
O4···H6iv2.50 (3)C18···H91i3.68 (4)
C12···C162.508 (6)C5···H81viii3.68 (3)
C1···C72.514 (6)C9···C17v3.686 (5)
C9···C152.516 (6)C3···C8viii3.689 (5)
O2···H1022.52 (3)C12···O53.698 (4)
C4···C82.520 (5)C3···H161viii3.70 (5)
C6···C82.534 (6)C7···O4ii3.713 (4)
C14···C162.535 (7)C8···O4vi3.716 (5)
H12···H1622.54 (5)C15···H182xiii3.72 (3)
N···O42.542 (4)C10···C17v3.720 (5)
N···O12.557 (4)C2···H181ix3.72 (4)
H92···H182v2.56 (5)C10···H102v3.73 (4)
C1···C32.562 (5)C2···H192ix3.73 (3)
C2···C92.564 (5)C19···O2xii3.730 (5)
C5···C162.569 (5)C3···H63.73 (2)
H6···H812.57 (4)C11···H143.74 (3)
C1···C102.571 (5)C2···C123.736 (5)
C8···C132.571 (6)C11···C163.737 (6)
C19···N2.577 (5)C13···H181xiii3.74 (4)
C9···C112.582 (5)C4···H73.74 (3)
C18···N2.583 (5)C7···H43.74 (2)
C3···O12.587 (4)C1···H173.74 (3)
C4···H822.59 (3)C15···H123.74 (3)
O1···H82vi2.59 (4)C12···H153.75 (3)
N···H922.60 (4)C7···H143.75 (3)
C11···O42.601 (4)C7···C133.755 (5)
C14···H1612.60 (5)C6···C123.755 (5)
H82···H181vi2.61 (4)C14···H181xiii3.76 (4)
C3···O22.613 (4)C1···C63.758 (6)
C1···H72.61 (3)C6···C12ii3.758 (5)
C11···O52.620 (4)C3···C83.759 (5)
C12···H1622.63 (4)C4···O23.759 (4)
O4···H4vi2.63 (3)C4···C103.761 (5)
C7···H1012.65 (4)C15···C163.762 (6)
H102···H912.66 (5)C9···C143.764 (6)
H92···H172.67 (5)C12···N3.767 (4)
C8···H62.67 (3)C9···H191xi3.77 (4)
C8···H42.67 (3)S2···H82vi3.77 (3)
C9···H152.67 (4)C7···C12ii3.769 (5)
O5···H191v2.67 (4)C7···C83.770 (6)
O5···H922.68 (3)C9···C15i3.778 (6)
C16···H142.68 (3)C1···H191xi3.78 (4)
C17···S22.682 (4)N···H43.78 (3)
O1···H12vi2.68 (3)S2···H1913.79 (4)
C12···S22.684 (4)C3···C133.786 (4)
C4···S12.685 (3)O1···H161vii3.79 (3)
C17···S12.688 (4)C15···H101v3.79 (4)
C15···H912.70 (4)C6···H81viii3.79 (3)
O2···H14vii2.70 (3)C7···H182ix3.79 (3)
S2···H122.71 (3)C19···S13.794 (4)
O5···H182v2.71 (3)O2···H161vii3.80 (4)
C3···H81viii2.72 (3)C15···H63.80 (3)
N···H1922.73 (3)C1···C43.802 (5)
H101···H922.73 (4)C1···H182ix3.81 (4)
C11···H922.73 (4)C14···O4ii3.806 (5)
C3···N2.735 (4)C7···C113.806 (5)
N···H1812.74 (4)C11···H1023.81 (3)
C3···C62.738 (5)S1···H1823.81 (3)
H82···H192vi2.74 (4)C9···O2v3.811 (5)
C2···C102.738 (5)C18···S23.812 (4)
C11···C142.740 (5)C9···C123.812 (5)
H81···H1622.74 (4)C17···H82vi3.82 (3)
C5···C132.742 (5)C2···C143.816 (5)
C16···H122.74 (3)C1···H91i3.82 (4)
C4···C72.749 (5)C4···C8viii3.820 (5)
C12···C152.754 (5)C6···C103.821 (5)
O1···H1812.76 (3)C1···C15i3.823 (6)
O1···H162vi2.76 (4)C11···H6iv3.83 (3)
C2···S12.762 (3)O5···H123.83 (3)
C6···H812.76 (3)C9···S13.839 (4)
C11···N2.776 (4)C4···O1vi3.839 (4)
C3···H1022.78 (4)C2···C19ix3.840 (6)
C17···O52.786 (5)C2···C18ix3.844 (5)
C10···S22.789 (4)C5···O4vi3.844 (4)
C10···H17v2.79 (2)C5···C153.844 (5)
H91···H17v2.80 (5)C6···C16viii3.846 (6)
S1···H42.80 (3)C7···C18ix3.850 (6)
S2···H922.82 (4)N···H123.85 (3)
C17···O22.817 (4)C1···C18ix3.854 (6)
C12···O42.827 (4)C7···H913.86 (3)
H101···H15i2.83 (5)C19···H81vi3.86 (3)
H82···H1612.84 (5)C14···H91v3.86 (4)
C4···O12.837 (4)C10···H182v3.86 (3)
O4···H1922.84 (3)O2···H191ix3.87 (4)
H102···H91i2.84 (5)C3···C153.875 (5)
N···H1022.84 (4)C4···H1623.88 (4)
C10···C132.848 (5)C4···S23.882 (3)
C2···C52.849 (5)S2···H182v3.88 (3)
H92···H15i2.86 (5)C14···H92v3.89 (4)
S1···H1022.86 (4)O2···H92i3.89 (4)
O4···H82vi2.86 (4)S2···H4vi3.89 (3)
H4···H122.87 (4)S1···H14vii3.89 (3)
H101···H191ix2.88 (6)C9···C173.892 (5)
H102···H191ix2.89 (6)C2···O13.893 (4)
S1···H1812.89 (4)O1···H1923.89 (3)
O5···H1922.89 (3)S2···H43.90 (2)
S2···H1922.90 (3)C18···H102xii3.90 (4)
C3···C112.910 (4)C6···O1xiv3.902 (5)
O2···H91i2.91 (3)O2···H1013.91 (4)
H162···H181vi2.92 (4)C8···O2xiv3.906 (5)
H17···H1922.93 (4)S1···H1923.91 (3)
C4···C122.928 (5)C9···C18v3.910 (6)
H181···H1912.93 (4)S2···H191v3.91 (3)
C1···H15i2.94 (3)C3···O43.911 (4)
O2···H1812.95 (4)C6···H153.91 (3)
H182···H1922.95 (4)O1···O4vi3.912 (4)
O5···H172.95 (3)C1···O5xi3.915 (5)
H92···H17v2.96 (5)S1···H6viii3.92 (3)
S1···S22.989 (1)C18···H81vi3.92 (3)
H17···H1812.99 (3)C10···O43.918 (4)
C6···H161viii3.00 (4)O2···H82viii3.92 (3)
O5···H101x3.00 (3)O5···H14iv3.92 (3)
C4···H81viii3.00 (3)C10···H92v3.92 (4)
C19···O53.005 (6)C18···H162vi3.92 (4)
C9···H17v3.01 (3)O2···H923.93 (4)
H101···H191xi3.01 (6)C3···H6viii3.93 (3)
H102···H173.01 (5)S2···H1813.94 (4)
O2···H192ix3.02 (3)S2···H1023.94 (4)
C5···H161viii3.02 (4)C4···C143.946 (5)
H91···H15i3.05 (6)C13···O1vi3.946 (5)
H91···H191xi3.05 (6)C2···C133.949 (5)
C4···H123.06 (3)C1···S23.950 (4)
C18···O23.060 (5)C5···C103.952 (5)
O2···H81viii3.07 (3)C15···H1613.95 (5)
C5···C123.072 (5)S1···H162vi3.95 (4)
C12···H43.07 (3)C5···C16viii3.955 (5)
H101···H182ix3.08 (5)C3···H823.96 (3)
C17···H923.08 (4)C8···H161viii3.96 (4)
O1···H4vi3.09 (3)C2···H182ix3.96 (4)
H4···H6viii3.09 (4)C15···H191xi3.96 (4)
C6···H12ii3.10 (3)O4···H1813.96 (4)
O4···H14iv3.12 (3)C2···H161viii3.97 (5)
C2···O23.116 (4)C2···S23.970 (3)
O2···H173.12 (3)C2···H191ix3.98 (4)
C5···H1613.13 (3)N···H91i3.98 (4)
H6···H143.14 (4)C4···O43.984 (4)
C9···N3.136 (5)S2···H17v3.98 (3)
H15···H191xi3.14 (5)O5···H102x3.99 (4)
H4···H4vi3.14 (3)C4···C16viii3.986 (5)
C2···H923.14 (4)C11···H1623.99 (4)
C2···C113.143 (4)C13···S23.997 (4)
C7···C153.149 (5)C10···S13.997 (4)
C6···C143.150 (5)C5···S14.000 (3)
H81···H192vi3.15 (4)C13···H182xiii4.00 (3)
C9···H15i3.16 (4)C19···H15x4.00 (3)
H7···H153.16 (5)C14···H814.00 (3)
O1···H6viii3.16 (3)C7···S14.002 (4)
C13···H823.16 (3)O5···H914.00 (4)
H4···H12vi3.17 (4)S2···H14iv4.00 (3)
H7···H12ii3.17 (4)C1···C174.006 (5)
C18···S13.169 (4)C14···C18xiii4.006 (6)
C19···S23.170 (5)C6···C114.012 (5)
S2···H173.17 (3)C4···H4vi4.01 (2)
C3···C103.172 (5)C6···H1014.01 (4)
C10···H1013.18 (3)C17···H182v4.02 (3)
C10···O53.181 (4)C4···H12vi4.02 (3)
S1···H81viii3.18 (3)C15···S24.035 (4)
C6···C133.187 (5)C18···O54.036 (5)
C8···C123.193 (5)C6···H162viii4.04 (4)
C4···C113.194 (5)C7···C124.040 (5)
C1···O23.197 (5)S1···H12vi4.04 (3)
C15···H73.20 (3)C8···C18vi4.042 (6)
H102···H192ix3.20 (5)C3···C174.043 (5)
C2···H81viii3.20 (3)C16···C16iii4.045 (6)
C16···H162iii3.21 (3)C11···C174.053 (5)
C1···S13.209 (4)C15···O5ii4.056 (5)
H161···H162iii3.21 (5)C19···O14.061 (5)
C19···H102xii3.21 (4)S1···H91i4.07 (3)
C14···H1623.22 (4)C19···O24.071 (5)
C12···H6iv3.22 (3)C2···C8viii4.075 (5)
C1···N3.218 (5)O2···S24.076 (3)
C19···H101xii3.22 (4)C13···O2xiii4.077 (4)
H91···H182v3.23 (5)C7···C16viii4.086 (6)
C8···H181vi3.23 (3)C5···O1vi4.087 (4)
C10···H1023.23 (3)O5···S14.093 (3)
C15···H102v3.23 (4)C12···S14.099 (4)
H81···H181vi3.23 (4)S1···H1014.12 (4)
O5···H17v3.23 (3)S2···H914.12 (4)
C4···H161viii3.24 (4)C7···C11ii4.132 (5)
C4···C133.239 (5)C18···O44.133 (5)
C2···C153.243 (5)C11···O14.133 (4)
O5···H1913.25 (5)S1···H124.14 (4)
C3···H73.25 (3)S1···H192ix4.14 (3)
C9···S23.250 (4)C8···S1xiv4.139 (4)
C4···H63.25 (3)C8···C19vi4.143 (6)
C15···H17v3.25 (3)S1···H4vi4.14 (2)
O1···O43.257 (4)C3···C144.148 (5)
C6···H43.26 (3)C7···S2ii4.150 (4)
C2···H913.26 (3)C4···C154.150 (5)
C12···H143.26 (3)C15···O2xiii4.152 (5)
C7···C103.265 (5)C9···O24.171 (5)
C11···H153.27 (4)C7···O5ii4.174 (5)
S1···H173.27 (2)S2···H15iv4.18 (4)
C3···C123.269 (4)C6···S2ii4.192 (4)
H6···H1613.27 (5)C15···C17v4.209 (5)
H15···H17v3.27 (5)C13···O44.210 (4)
C14···H63.28 (3)C8···C114.222 (5)
C6···C163.279 (6)C7···C8viii4.227 (6)
C12···H7iv3.28 (3)C5···O14.230 (4)
C15···H92v3.28 (4)C3···C16viii4.230 (6)
C9···H182v3.28 (3)C15···O4ii4.241 (5)
C4···H813.28 (3)C13···C18xiii4.253 (6)
H82···H123.29 (4)C1···C54.263 (5)
C5···H1623.29 (3)C9···C134.269 (5)
H7···H182ix3.29 (4)C2···C84.282 (5)
C14···H123.29 (3)C10···C164.284 (6)
C6···H823.30 (3)S1···H161vii4.30 (4)
C12···H1613.30 (4)C8···O1xiv4.304 (5)
C8···H123.31 (3)C7···C164.307 (6)
N···H1913.31 (4)C9···C14i4.310 (6)
C5···H73.31 (3)C5···C8viii4.314 (5)
C1···H191ix3.31 (4)C10···C18v4.338 (6)
C5···C143.309 (5)C4···C6viii4.342 (5)
C15···H923.31 (4)C1···C144.350 (6)
C7···H1023.31 (4)C7···C19ix4.351 (6)
C13···H153.31 (3)C6···C8viii4.353 (6)
C6···O4ii3.312 (4)C5···O1xiv4.354 (4)
C6···H143.32 (3)C6···C11ii4.357 (5)
C16···H63.32 (3)C11···C17v4.359 (5)
O4···H7iv3.32 (3)C4···C94.361 (5)
C13···H813.32 (3)C14···O5ii4.369 (5)
O5···H15iv3.33 (4)C12···O14.380 (4)
H14···H192ii3.33 (4)C1···C124.387 (5)
C3···C93.329 (5)C16···O1xiii4.391 (5)
C10···H123.33 (3)C7···O24.391 (4)
O2···H1823.33 (3)C5···O2xiv4.398 (5)
C1···C153.332 (6)C6···C94.398 (5)
H7···H191xi3.33 (3)C3···C164.400 (5)
C8···O1vi3.332 (5)C15···C18xiii4.403 (6)
C18···H101xii3.33 (3)C9···C19xi4.404 (6)
C10···N3.334 (4)C16···C18vi4.419 (7)
O5···H7iv3.34 (3)C1···C19xi4.434 (6)
N···H1823.34 (3)C8···C154.434 (6)
C17···H1023.34 (4)C10···C174.438 (5)
H6···H161viii3.34 (4)C14···S1xiii4.465 (4)
C2···H63.34 (3)C8···S1vi4.472 (4)
C10···H143.35 (3)C6···S14.487 (4)
C14···O2xiii3.345 (4)C14···S24.510 (4)
C2···N3.350 (4)C6···S1xiv4.570 (4)
C17···H91i3.35 (4)C18···S2i4.602 (5)
C18···H92i3.35 (4)C14···S2ii4.611 (4)
C2···H43.36 (2)C5···S1xiv4.614 (3)
C18···H82vi3.36 (3)C19···S2i4.632 (5)
C3···H1013.36 (4)C17···S2i4.640 (4)
C9···O53.366 (5)C16···S1vi4.659 (5)
C19···O5i3.366 (6)C15···S2ii4.667 (4)
H101—C1—H102107 (4)C12—C13—C16119.4 (3)
H101—C1—C2112 (2)H14—C14—C15122 (2)
H101—C1—C9107 (2)H14—C14—C13117 (2)
H102—C1—C2113 (2)C15—C14—C13120.7 (4)
H102—C1—C9105 (2)H15—C15—C14121 (2)
C2—C1—C9112.5 (3)H15—C15—C10117 (2)
C7—C2—C3114.2 (3)C14—C15—C10122.5 (4)
C7—C2—C1120.7 (3)H162—C16—H161111 (3)
C3—C2—C1123.9 (3)H162—C16—C13104 (2)
C4—C3—C2122.2 (3)H162—C16—C8112 (2)
C4—C3—S1116.6 (2)H161—C16—C13108 (3)
C2—C3—S1121.1 (2)H161—C16—C8109 (3)
H4—C4—C3122 (2)C13—C16—C8112.2 (3)
H4—C4—C5118 (2)H17—C17—N112 (2)
C3—C4—C5120.1 (3)H17—C17—C18120 (2)
C6—C5—C4116.8 (3)H17—C17—C19115 (2)
C6—C5—C8122.1 (3)N—C17—C18120.7 (3)
C4—C5—C8120.0 (3)N—C17—C19120.1 (3)
H6—C6—C5116 (2)C18—C17—C1959.0 (3)
H6—C6—C7122 (2)H182—C18—H181120 (3)
C5—C6—C7121.2 (3)H182—C18—C19119 (2)
H7—C7—C6121 (2)H182—C18—C17112 (2)
H7—C7—C2115 (2)H181—C18—C19115 (2)
C6—C7—C2122.1 (3)H181—C18—C17117 (2)
H82—C8—H81103 (3)C19—C18—C1760.5 (3)
H82—C8—C5108 (2)H191—C19—H192121 (3)
H82—C8—C16111 (2)H191—C19—C18117 (3)
H81—C8—C5112 (2)H191—C19—C17109 (2)
H81—C8—C16110 (2)H192—C19—C18116 (2)
C5—C8—C16112.2 (3)H192—C19—C17117 (2)
H92—C9—H91107 (3)C18—C19—C1760.5 (3)
H92—C9—C10110 (2)C17—N—S2116.0 (2)
H92—C9—C1106 (2)C17—N—S1116.1 (2)
H91—C9—C10112 (2)S2—N—S1124.4 (2)
H91—C9—C1109 (2)O1—S1—O2118.6 (2)
C10—C9—C1112.4 (3)O1—S1—N109.8 (2)
C15—C10—C11114.0 (3)O1—S1—C3108.4 (2)
C15—C10—C9119.9 (3)O2—S1—N104.2 (2)
C11—C10—C9124.2 (3)O2—S1—C3109.8 (1)
C12—C11—C10122.8 (3)N—S1—C3105.0 (1)
C12—C11—S2116.0 (2)O4—S2—O5119.0 (2)
C10—C11—S2121.2 (2)O4—S2—N109.2 (1)
H12—C12—C11117 (2)O4—S2—C11108.1 (2)
H12—C12—C13123 (2)O5—S2—N104.5 (2)
C11—C12—C13120.0 (3)O5—S2—C11108.8 (2)
C14—C13—C12117.6 (4)N—S2—C11106.6 (1)
C14—C13—C16121.5 (4)
C9—C1—C2—C376.7 (4)C10—C11—C12—C130.8 (5)
C9—C1—C2—C790.1 (4)C10—C11—C12—H12176 (2)
H101—C1—C2—C3163 (3)S2—C11—C12—C13177.1 (3)
H101—C1—C2—C730 (3)S2—C11—C12—H122 (2)
H102—C1—C2—C343 (3)C10—C11—S2—N60.6 (3)
H102—C1—C2—C7151 (3)C10—C11—S2—O4177.9 (3)
C2—C1—C9—C105.3 (4)C10—C11—S2—O551.6 (3)
C2—C1—C9—H91130 (2)C12—C11—S2—N117.4 (3)
C2—C1—C9—H92115 (2)C12—C11—S2—O40.1 (3)
H101—C1—C9—C10118 (2)C12—C11—S2—O5130.4 (3)
H101—C1—C9—H917 (3)C11—C12—C13—C1413.2 (5)
H101—C1—C9—H92122 (3)C11—C12—C13—C16153.2 (3)
H102—C1—C9—C10129 (3)H12—C12—C13—C14172 (2)
H102—C1—C9—H91106 (4)H12—C12—C13—C1622 (2)
H102—C1—C9—H929 (4)C12—C13—C14—C1513.3 (6)
C1—C2—C3—C4153.4 (3)C12—C13—C14—H14177 (2)
C1—C2—C3—S123.7 (4)C16—C13—C14—C15152.8 (4)
C7—C2—C3—C414.1 (4)C16—C13—C14—H1417 (2)
C7—C2—C3—S1168.8 (2)C12—C13—C16—C869.7 (5)
C1—C2—C7—C6153.1 (4)C12—C13—C16—H161170 (2)
C1—C2—C7—H711 (2)C12—C13—C16—H16252 (3)
C3—C2—C7—C614.9 (5)C14—C13—C16—C896.1 (4)
C3—C2—C7—H7179 (2)C14—C13—C16—H16124 (3)
C2—C3—C4—C50.6 (5)C14—C13—C16—H162143 (3)
C2—C3—C4—H4172 (2)C13—C14—C15—C100.8 (6)
S1—C3—C4—C5176.6 (2)C13—C14—C15—H15177 (2)
S1—C3—C4—H45 (2)H14—C14—C15—C10170 (2)
C2—C3—S1—N68.5 (3)H14—C14—C15—H158 (3)
C2—C3—S1—O1174.2 (2)C19—C17—C18—C190.0 (3)
C2—C3—S1—O243.1 (3)C19—C17—C18—H181104 (2)
C4—C3—S1—N108.8 (3)C19—C17—C18—H182112 (2)
C4—C3—S1—O18.6 (3)N—C17—C18—C19108.9 (4)
C4—C3—S1—O2139.7 (2)N—C17—C18—H1814 (2)
C3—C4—C5—C615.1 (5)N—C17—C18—H182140 (2)
C3—C4—C5—C8153.2 (3)H17—C17—C18—C19103 (2)
H4—C4—C5—C6173 (2)H17—C17—C18—H181152 (3)
H4—C4—C5—C819 (2)H17—C17—C18—H1828 (3)
C4—C5—C6—C714.5 (5)C18—C17—C19—C180.0 (3)
C4—C5—C6—H6175 (2)C18—C17—C19—H191111 (3)
C8—C5—C6—C7153.6 (4)C18—C17—C19—H192106 (2)
C8—C5—C6—H617 (2)N—C17—C19—C18109.9 (4)
C4—C5—C8—C1692.2 (4)N—C17—C19—H191140 (3)
C4—C5—C8—H81143 (2)N—C17—C19—H1924 (2)
C4—C5—C8—H8231 (2)H17—C17—C19—C18111 (2)
C6—C5—C8—C1675.5 (4)H17—C17—C19—H1910 (4)
C6—C5—C8—H8149 (2)H17—C17—C19—H192143 (3)
C6—C5—C8—H82162 (2)C18—C17—N—S143.9 (4)
C5—C6—C7—C20.9 (6)C18—C17—N—S2115.8 (3)
C5—C6—C7—H7164 (2)C19—C17—N—S1113.5 (3)
H6—C6—C7—C2169 (2)C19—C17—N—S246.2 (4)
H6—C6—C7—H76 (3)H17—C17—N—S1106 (2)
C5—C8—C16—C1311.8 (5)H17—C17—N—S294 (2)
C5—C8—C16—H161108 (3)C17—C18—C19—C170.0 (2)
C5—C8—C16—H162129 (2)C17—C18—C19—H19198 (3)
H81—C8—C16—C13137 (2)C17—C18—C19—H192108 (2)
H81—C8—C16—H16117 (4)H181—C18—C19—C17108 (2)
H81—C8—C16—H162106 (3)H181—C18—C19—H191153 (4)
H82—C8—C16—C13109 (2)H181—C18—C19—H1920 (3)
H82—C8—C16—H161131 (4)H182—C18—C19—C17100 (2)
H82—C8—C16—H1628 (3)H182—C18—C19—H1912 (4)
C1—C9—C10—C1180.0 (4)H182—C18—C19—H192151 (3)
C1—C9—C10—C1583.0 (4)C17—N—S1—C3151.0 (2)
H91—C9—C10—C11157 (2)C17—N—S1—O192.6 (3)
H91—C9—C10—C1540 (3)C17—N—S1—O235.5 (3)
H92—C9—C10—C1138 (2)S2—N—S1—C351.2 (2)
H92—C9—C10—C15159 (2)S2—N—S1—O165.2 (2)
C9—C10—C11—C12152.8 (3)S2—N—S1—O2166.7 (2)
C9—C10—C11—S225.1 (5)C17—N—S2—C11145.7 (2)
C15—C10—C11—C1211.1 (5)C17—N—S2—O497.7 (3)
C15—C10—C11—S2171.1 (3)C17—N—S2—O530.5 (3)
C9—C10—C15—C14153.5 (4)S1—N—S2—C1156.5 (2)
C9—C10—C15—H1524 (2)S1—N—S2—O460.1 (2)
C11—C10—C15—C1411.1 (5)S1—N—S2—O5171.6 (2)
C11—C10—C15—H15171 (2)
Symmetry codes: (i) x1/2, y, z+3/2; (ii) x+3/2, y1/2, z; (iii) x+2, y+1, z+1; (iv) x+3/2, y+1/2, z; (v) x+1/2, y, z+3/2; (vi) x+1, y+1, z+1; (vii) x1, y, z; (viii) x1/2, y+1/2, z+1; (ix) x+1/2, y1/2, z; (x) x+1, y+1/2, z+3/2; (xi) x+1, y1/2, z+3/2; (xii) x+1/2, y+1/2, z; (xiii) x+1, y, z; (xiv) x+1/2, y+1/2, z+1.
(PCF7) N-phenyl-[2.2]paracyclophane-4,15-disulfonimide top
Crystal data top
C22H19NS2O4F(000) = 888
Mr = 425.5Dx = 1.488 Mg m3
Orthorhombic, PmcnCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P -2n 21Cell parameters from 23 reflections
a = 9.915 (2) Åθ = 40.1–45.2°
b = 12.426 (1) ŵ = 2.81 mm1
c = 15.418 (2) ÅT = 293 K
V = 1899.6 (5) Å3Block, colourless
Z = 40.60 × 0.60 × 0.25 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
Radiation source: xray tubeθmax = 74.7°, θmin = 4.6°
Graphite monochromatorh = 120
θ/2θ scansk = 150
2069 measured reflectionsl = 019
2069 independent reflections2 standard reflections every 60 min
1793 reflections with refl observed if I > 2.5 σ(I ) intensity decay: none
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullRiding
R[F2 > 2σ(F2)] = 0.049 1/[5.2 + 0.0051*σ(Fobs)2 + 0.00003/σ(Fobs)]
wR(F2) = 0.054(Δ/σ)max = 0.077
S = 0.86Δρmax = 0.39 e Å3
1793 reflectionsΔρmin = 0.52 e Å3
185 parametersExtinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
12 restraintsExtinction coefficient: 7384 (230)
Crystal data top
C22H19NS2O4V = 1899.6 (5) Å3
Mr = 425.5Z = 4
Orthorhombic, PmcnCu Kα radiation
a = 9.915 (2) ŵ = 2.81 mm1
b = 12.426 (1) ÅT = 293 K
c = 15.418 (2) Å0.60 × 0.60 × 0.25 mm
Data collection top
ENRAF NONIUS CAD4
diffractometer
Rint = 0
2069 measured reflections2 standard reflections every 60 min
2069 independent reflections intensity decay: none
1793 reflections with refl observed if I > 2.5 σ(I )
Refinement top
R[F2 > 2σ(F2)] = 0.04912 restraints
wR(F2) = 0.054Riding
S = 0.86Δρmax = 0.39 e Å3
1793 reflectionsΔρmin = 0.52 e Å3
185 parameters
Special details top

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3311 (3)0.4714 (3)0.9892 (2)0.035 (2)
C20.3884 (3)0.3638 (3)0.9624 (2)0.030 (1)
C30.3983 (3)0.3286 (2)0.8763 (2)0.027 (1)
C40.3991 (3)0.2195 (3)0.8547 (2)0.031 (1)
C50.3882 (3)0.1424 (3)0.9195 (2)0.035 (2)
C60.4090 (3)0.1766 (3)1.0042 (2)0.040 (2)
C70.4100 (3)0.2850 (3)1.0251 (2)0.038 (2)
C80.3298 (4)0.0330 (3)0.8998 (3)0.049 (2)
C170.250000.5885 (4)0.7493 (4)0.037 (2)
C180.250000.5904 (5)0.6596 (4)0.045 (3)
C190.250000.6887 (6)0.6170 (5)0.068 (4)
C200.250000.7816 (6)0.6620 (8)0.085 (6)
C210.250000.7803 (6)0.7507 (8)0.080 (5)
C220.250000.6816 (5)0.7971 (5)0.061 (4)
N0.250000.4851 (3)0.7956 (2)0.029 (2)
S0.40094 (7)0.41988 (6)0.78910 (4)0.0292 (4)
O10.4099 (3)0.3608 (2)0.7100 (1)0.043 (1)
O20.4977 (2)0.5032 (2)0.8058 (2)0.043 (1)
H1010.362 (3)0.486 (3)1.050 (1)0.04 (1)*
H1020.363 (3)0.529 (2)0.949 (2)0.032 (9)*
H40.397 (4)0.200 (3)0.7925 (8)0.04 (1)*
H60.407 (4)0.123 (2)1.052 (2)0.039 (9)*
H70.407 (4)0.308 (3)1.0870 (9)0.05 (1)*
H810.359 (4)0.008 (3)0.842 (1)0.07 (1)*
H820.366 (4)0.019 (2)0.943 (2)0.06 (1)*
H220.250000.679 (5)0.8617 (9)0.05 (1)*
H180.250000.521 (2)0.628 (3)0.05 (1)*
H190.250000.691 (6)0.5523 (9)0.09 (2)*
H200.250000.856 (2)0.637 (4)0.07 (2)*
H210.250000.841 (4)0.794 (4)0.10 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.025 (2)0.050 (2)0.032 (2)0.003 (1)0.004 (1)0.013 (1)
C20.013 (1)0.047 (2)0.028 (1)0.003 (1)0.003 (1)0.004 (1)
C30.014 (1)0.042 (2)0.026 (1)0.001 (1)0.000 (1)0.000 (1)
C40.019 (1)0.044 (2)0.029 (1)0.004 (1)0.003 (1)0.004 (1)
C50.021 (1)0.041 (2)0.043 (2)0.007 (1)0.005 (1)0.003 (1)
C60.027 (2)0.056 (2)0.037 (2)0.006 (2)0.001 (1)0.012 (2)
C70.023 (1)0.063 (2)0.026 (1)0.002 (2)0.003 (1)0.000 (1)
C80.043 (2)0.039 (2)0.065 (3)0.003 (2)0.014 (2)0.002 (2)
C170.021 (2)0.034 (2)0.057 (3)0.000000.000000.007 (2)
C180.032 (2)0.051 (3)0.053 (3)0.000000.000000.016 (3)
C190.034 (3)0.074 (5)0.095 (6)0.000000.000000.044 (4)
C200.034 (3)0.056 (5)0.165 (9)0.000000.000000.044 (5)
C210.051 (4)0.038 (4)0.152 (8)0.000000.000000.014 (5)
C220.050 (3)0.043 (3)0.091 (5)0.000000.000000.016 (3)
N0.018 (2)0.034 (2)0.035 (2)0.000000.000000.001 (2)
S0.0203 (4)0.0423 (4)0.0250 (4)0.0014 (3)0.0034 (3)0.0015 (3)
O10.047 (1)0.055 (1)0.027 (1)0.012 (1)0.007 (1)0.000 (1)
O20.024 (1)0.053 (1)0.053 (1)0.009 (1)0.002 (1)0.006 (1)
Geometric parameters (Å, º) top
C1—H1011.00 (2)C8—C8i1.583 (6)
C1—H1021.00 (3)C17—C221.372 (8)
C1—C21.511 (5)C17—C181.383 (8)
C1—C1i1.608 (4)C17—N1.469 (6)
C2—C71.393 (5)C18—H181.00 (4)
C2—C31.401 (4)C18—C191.39 (1)
C3—C41.396 (4)C19—H191.00 (2)
C3—S1.759 (3)C19—C201.35 (1)
C4—H40.99 (2)C20—H201.00 (3)
C4—C51.389 (5)C20—C211.37 (2)
C5—C61.388 (5)C21—H211.00 (6)
C5—C81.508 (5)C21—C221.42 (1)
C6—H61.00 (2)C22—H221.00 (2)
C6—C71.385 (5)N—Si1.705 (2)
C7—H71.00 (2)N—S1.705 (2)
C8—H810.99 (3)S—O11.426 (2)
C8—H821.00 (3)S—O21.435 (3)
H81···H821.60 (4)O2···H223.40 (4)
H101···H1021.65 (3)H102···H20v3.42 (6)
C22···H211.98 (6)C1···C1vi3.440 (4)
C21···H201.99 (5)C3···Si3.449 (3)
C20···H192.03 (4)C6···C7i3.453 (5)
C2···H1012.05 (3)C1···H7i3.46 (3)
C2···H72.05 (2)C8···H4i3.48 (3)
C5···H822.05 (3)C6···H18vii3.48 (4)
C3···H42.05 (3)C18···H6ii3.49 (3)
C7···H62.06 (3)C18···H6xii3.49 (3)
C17···H182.06 (5)H7···H22xiii3.49 (4)
C17···H222.07 (3)C6···H19ix3.496 (6)
C5···H62.07 (2)C3···H101vi3.51 (3)
C6···H72.07 (3)C18···O23.505 (5)
C18···H192.07 (5)C18···O2i3.505 (5)
C5···H812.08 (4)C8···H6i3.51 (3)
C2···H1022.08 (2)C3···H20ix3.510 (5)
C5···H42.09 (2)C5···H4i3.51 (3)
C19···H182.10 (3)H102···H73.51 (4)
C8···H81i2.10 (4)H101···H7i3.51 (5)
C19···H202.10 (3)C4···C19ix3.528 (3)
C21···H222.12 (4)C1···C2vi3.533 (4)
C1···H101i2.13 (3)C20···H101xiv3.55 (3)
C1···H102i2.15 (3)C20···H101xv3.55 (3)
C8···H82i2.15 (4)O2···H21ix3.56 (4)
C20···H212.16 (6)H4···H81i3.57 (5)
H81···H81i2.16 (6)O1···H82viii3.57 (3)
H101···H101i2.21 (5)C21···O1xvi3.570 (4)
H102···H102i2.24 (5)C21···O1viii3.570 (4)
H22···H212.26 (8)C2···H7i3.57 (3)
H82···H82i2.30 (5)C3···H4i3.57 (3)
H101···H72.33 (5)C5···H82iv3.57 (3)
C19···C212.35 (1)C4···C20ix3.573 (4)
H6···H72.36 (4)H6···H813.58 (4)
C3···C72.360 (4)C5···H6i3.58 (3)
C4···C62.367 (4)C22···S3.582 (6)
O1···H42.37 (3)C22···Si3.582 (6)
C18···C202.38 (1)C3···C20ix3.585 (4)
C17···C212.384 (8)H4···H823.60 (4)
C17···C192.39 (1)C19···H82ii3.60 (3)
C18···C222.403 (9)C19···H82xii3.60 (3)
C3···C52.411 (4)C1···O2vi3.601 (4)
H18···H192.42 (7)S···H101vi3.62 (3)
C5···C72.416 (5)C8···O2xvii3.621 (5)
H20···H212.42 (8)C18···H82ii3.64 (3)
C2···C62.423 (5)C18···H82xii3.64 (3)
C20···C222.43 (1)C8···H18vii3.66 (5)
H19···H202.43 (7)C5···H19ix3.66 (1)
O1···H6ii2.44 (2)C4···H81i3.68 (4)
C22···N2.442 (7)C5···C19ix3.677 (4)
C2···C42.446 (4)C7···H101i3.69 (3)
H81···H21iii2.46 (6)O2···H183.69 (4)
O1···O22.464 (3)S···H6ii3.69 (2)
C18···N2.471 (7)C21···H4xvi3.70 (4)
N···O2i2.472 (2)C21···H4viii3.70 (4)
N···O22.472 (2)C20···H4xvi3.71 (4)
H6···H822.47 (4)C20···H4viii3.71 (4)
C1···C72.507 (5)C3···C5i3.724 (4)
C4···C82.515 (5)S···H223.73 (5)
C6···C82.527 (5)C3···H63.73 (2)
H4···H812.54 (5)C8···H19vii3.73 (6)
H102···H222.55 (5)S···H20ix3.73 (2)
C7···H1012.57 (3)C4···N3.729 (5)
C5···C8i2.571 (5)C18···H213.73 (6)
C1···C32.574 (4)C21···N3.732 (8)
N···O1i2.576 (4)C4···O23.736 (4)
N···O12.576 (4)C19···N3.739 (9)
C1···C2i2.588 (4)C7···H43.74 (2)
H6···H82iv2.59 (5)C21···H183.74 (4)
O2···H1022.60 (3)C4···H73.75 (2)
C3···O12.598 (3)C17···H203.75 (4)
N···H222.62 (5)C1···C63.751 (5)
C3···O22.619 (4)C3···C83.753 (5)
N···H182.63 (5)C20···O2viii3.753 (7)
H101···H20v2.63 (5)C20···O2xvi3.753 (7)
O2···H101vi2.63 (2)C2···C4i3.755 (4)
H6···H18vii2.64 (4)C6···H7i3.76 (4)
C1···H72.64 (3)C8···O1xvii3.756 (5)
C6···H822.64 (3)C7···H6i3.76 (3)
C17···Si2.646 (4)C7···H19ix3.76 (2)
C17···S2.646 (4)C7···C83.764 (5)
C4···H812.67 (4)C3···H102i3.77 (3)
N···H102i2.67 (3)C6···H82i3.77 (4)
N···H1022.67 (3)C22···H4xvi3.77 (3)
O2···H81viii2.68 (3)C22···H4viii3.77 (3)
C4···S2.688 (3)C19···H4xvi3.77 (3)
C8···H62.71 (3)C19···H4viii3.77 (3)
S···H42.73 (3)C19···H223.77 (2)
C3···C62.733 (5)C22···H193.78 (2)
C8···H42.74 (3)C4···H19ix3.780 (9)
C3···N2.737 (4)C4···O2xvii3.794 (4)
H101···H102vi2.74 (5)C2···C6i3.811 (5)
C5···C5i2.740 (4)C5···C7i3.812 (5)
H81···H82i2.74 (5)C1···C43.815 (5)
C18···C212.74 (1)C7···O2vi3.816 (4)
C2···C2i2.745 (4)C7···H101vi3.82 (3)
C17···C202.75 (1)S···H21ix3.82 (2)
C4···C72.752 (4)C7···H22xiii3.82 (1)
C3···H1022.76 (2)C17···H4xvi3.82 (4)
C2···S2.764 (3)C17···H4viii3.82 (4)
H101···H102i2.77 (4)N···H4i3.83 (3)
C19···C222.78 (1)N···H43.83 (3)
C17···O2i2.813 (3)C18···H4xvi3.83 (4)
C17···O22.813 (3)C18···H4viii3.83 (4)
O1···H7ii2.82 (3)C21···O2xvi3.833 (6)
C2···C52.830 (5)C21···O2viii3.833 (6)
S···H1022.84 (3)C4···C18ix3.838 (4)
O1···H182.84 (3)S···H102i3.84 (3)
C4···O12.842 (4)C22···H7xviii3.84 (3)
H4···H4i2.91 (5)C22···H7vi3.84 (3)
C3···C3i2.940 (4)C5···C18ix3.844 (4)
H82···H19vii2.95 (6)O1···H4i3.85 (3)
C4···C4i2.956 (4)C3···C7i3.860 (4)
S···Si2.993 (1)C4···C6i3.863 (5)
C8···H21iii3.00 (6)C6···C19ix3.866 (5)
O2···H7vi3.02 (3)C8···H82iv3.87 (4)
O1···H81viii3.04 (4)C4···H20ix3.87 (1)
O2···H4viii3.06 (3)C5···H6iv3.90 (3)
H82···H18vii3.07 (6)C2···O13.898 (4)
C6···H82iv3.08 (4)C3···C19ix3.899 (5)
C4···H4i3.09 (4)C2···H20ix3.90 (2)
C1···N3.097 (5)C1···Si3.902 (3)
H102···H7vi3.10 (5)O2···H43.90 (3)
C2···H101vi3.11 (3)C4···C21ix3.914 (6)
H82···H21iii3.11 (6)C21···Sxvi3.920 (4)
H7···H7i3.11 (5)C21···Sviii3.920 (4)
C2···H102vi3.12 (3)C6···H1013.94 (3)
H6···H6i3.12 (5)C20···Sxvi3.937 (4)
C1···H101vi3.15 (3)C20···Sviii3.937 (4)
C6···C6i3.153 (5)C2···C5i3.941 (4)
S···H183.16 (4)C1···H7vi3.96 (3)
C2···O23.163 (4)C6···C8iv3.960 (5)
H101···H101vi3.16 (4)C5···H18ix3.96 (2)
C4···C5i3.167 (4)C8···C21iii3.97 (1)
C2···C3i3.168 (4)C1···C7vi3.975 (5)
O1···O1i3.170 (4)O1···H6xii3.98 (3)
H4···H7ii3.17 (2)C2···Si3.982 (3)
C7···C7i3.172 (5)C5···S3.994 (3)
C1···H102vi3.18 (3)C3···H102vi4.00 (3)
C5···H81i3.20 (4)O2···H1014.00 (2)
C2···H101i3.20 (3)C7···S4.007 (3)
C6···O1vii3.207 (4)C3···O1i4.009 (4)
C17···H213.21 (6)C4···Si4.009 (3)
C22···H102i3.21 (3)C7···H82iv4.01 (3)
C22···H1023.21 (3)C18···H81viii4.01 (4)
H82···H82iv3.22 (5)C18···H81xvi4.01 (4)
O2···H20ix3.22 (2)C7···H824.01 (3)
C1···S3.227 (3)S···H4i4.02 (4)
H102···H102vi3.23 (4)C6···H81iv4.02 (4)
C1···H20v3.23 (4)C20···O1xvi4.030 (7)
C2···H102i3.24 (3)C20···O1viii4.030 (7)
C5···H82i3.24 (4)C1···C224.031 (8)
C7···H102vi3.25 (3)C5···H18vii4.03 (4)
C5···C6i3.251 (5)C3···H19ix4.04 (3)
C21···H193.25 (3)C5···O2xvii4.042 (4)
C3···H73.26 (1)C22···O1viii4.043 (4)
C3···C4i3.262 (4)C22···O1xvi4.043 (4)
C2···C7i3.263 (4)C3···C21ix4.044 (6)
H6···H81iv3.27 (5)C3···C174.052 (6)
C18···Si3.274 (5)C1···C174.055 (6)
C18···S3.274 (5)C3···C6i4.091 (5)
C4···H63.27 (2)S···O2i4.094 (3)
C6···H43.28 (1)C2···O2vi4.096 (4)
C22···H203.28 (5)C4···C7i4.117 (4)
C2···N3.282 (4)S···H1014.12 (2)
C4···H823.28 (3)C1···C20v4.14 (1)
C20···H183.29 (3)C4···C17ix4.163 (4)
C7···H1023.29 (2)C5···C20ix4.176 (6)
C6···H6i3.29 (4)C4···O1i4.177 (4)
C22···H183.29 (5)C2···C20ix4.192 (7)
C17···H193.29 (3)C8···Sxvii4.194 (4)
C7···H7i3.30 (4)C7···C19ix4.195 (6)
C17···O1i3.298 (5)C1···C3vi4.204 (4)
C17···O13.298 (5)C2···C2vi4.206 (4)
C1···O23.299 (4)S···H7ii4.21 (2)
C2···H63.30 (3)S···H4viii4.21 (3)
C5···H73.30 (2)C4···C22ix4.220 (5)
C6···H813.31 (3)C20···N4.22 (1)
C18···H223.31 (2)C5···O14.225 (4)
S···H81viii3.31 (4)C2···C84.262 (5)
C22···O23.312 (5)C1···C54.266 (5)
C22···O2i3.312 (5)C21···O24.314 (6)
C19···H213.31 (6)C21···O2i4.314 (6)
C18···H203.32 (3)C8···C18ix4.325 (4)
C4···C8i3.317 (5)C3···C8i4.329 (5)
C2···H43.32 (2)C1···O2i4.334 (4)
C3···H1013.33 (2)C6···C18ix4.354 (5)
C8···H6iv3.33 (3)C8···C18vii4.362 (7)
C20···H223.33 (3)C7···C22xiii4.365 (6)
C21···H81x3.34 (4)C2···C19ix4.369 (5)
C21···H81xi3.34 (4)C1···C6i4.375 (5)
C1···H223.34 (5)C7···C8i4.380 (5)
H22···H19v3.35 (5)C6···C18vii4.386 (7)
C17···H102i3.35 (3)C1···C4i4.394 (5)
C17···H1023.35 (3)C8···C19vii4.408 (9)
C18···O1i3.355 (6)C7···C20ix4.437 (8)
C18···O13.355 (6)C6···C20ix4.438 (8)
C1···C3i3.369 (4)C6···S4.488 (4)
C6···C8i3.373 (5)C19···S4.520 (8)
C1···C7i3.374 (5)C19···Si4.520 (8)
C7···O1vii3.378 (4)C1···Svi4.535 (3)
O1···H21ix3.382 (5)C6···Svii4.554 (3)
S···O1i3.394 (3)
H101—C1—H102111 (2)C5—C8—C8i112.6 (3)
H101—C1—C2108 (2)C22—C17—C18121.4 (5)
H101—C1—C1i108 (2)C22—C17—N118.5 (5)
H102—C1—C2110 (2)C18—C17—N120.1 (4)
H102—C1—C1i108 (2)H18—C18—C17119 (3)
C2—C1—C1i112.1 (3)H18—C18—C19122 (3)
C7—C2—C3115.3 (3)C17—C18—C19119.3 (6)
C7—C2—C1119.3 (3)H19—C19—C20119 (4)
C3—C2—C1124.2 (3)H19—C19—C18120 (4)
C4—C3—C2121.9 (3)C20—C19—C18120.7 (8)
C4—C3—S116.4 (2)H20—C20—C19126 (3)
C2—C3—S121.6 (2)H20—C20—C21113 (3)
H4—C4—C5122 (2)C19—C20—C21120.3 (8)
H4—C4—C3118 (2)H21—C21—C20131 (3)
C5—C4—C3119.9 (3)H21—C21—C22108 (3)
C6—C5—C4117.0 (3)C20—C21—C22121.0 (7)
C6—C5—C8121.5 (3)H22—C22—C17121 (3)
C4—C5—C8120.5 (3)H22—C22—C21122 (3)
H6—C6—C7119 (1)C17—C22—C21117.3 (7)
H6—C6—C5119 (1)C17—N—Si112.8 (1)
C7—C6—C5121.2 (3)C17—N—S112.8 (1)
H7—C7—C6120 (2)Si—N—S122.8 (2)
H7—C7—C2118 (2)O1—S—O2118.9 (1)
C6—C7—C2121.4 (3)O1—S—N110.4 (2)
H81—C8—H82107 (3)O1—S—C3108.9 (1)
H81—C8—C5111 (2)O2—S—N103.5 (2)
H81—C8—C8i107 (2)O2—S—C3109.8 (1)
H82—C8—C5108 (2)N—S—C3104.4 (2)
H82—C8—C8i111 (2)
H101—C1—C2—C3163 (2)C5—C6—C7—C20.9 (5)
H101—C1—C2—C730 (2)C5—C6—C7—H7168 (3)
H102—C1—C2—C341 (2)H6—C6—C7—C2168 (2)
H102—C1—C2—C7151 (2)H6—C6—C7—H71 (4)
C1i—C1—C2—C379.3 (4)C22—C17—C18—C190.0001 (1)
C1i—C1—C2—C787.8 (3)C22—C17—C18—H18180.0000
C1—C2—C3—C4153.8 (3)N—C17—C18—C19180.0000
C1—C2—C3—S22.7 (4)N—C17—C18—H180.0001
C7—C2—C3—C413.8 (4)C18—C17—C22—C210.0001 (1)
C7—C2—C3—S169.7 (2)C18—C17—C22—H22180.0000
C1—C2—C7—C6153.6 (3)N—C17—C22—C21180.0000
C1—C2—C7—H714 (3)N—C17—C22—H220.0001 (1)
C3—C2—C7—C614.6 (4)C18—C17—N—S72.2 (2)
C3—C2—C7—H7178 (3)C18—C17—N—Si72.2 (2)
C2—C3—C4—C50.8 (4)C22—C17—N—S107.8 (2)
C2—C3—C4—H4174 (2)C22—C17—N—Si107.8 (2)
S—C3—C4—C5175.8 (2)C17—C18—C19—C200.0001 (1)
S—C3—C4—H43 (2)C17—C18—C19—H19180.0000
C2—C3—S—N61.4 (3)H18—C18—C19—C20180.0000
C2—C3—S—O1179.3 (2)H18—C18—C19—H190.0001 (3)
C2—C3—S—O249.0 (3)C18—C19—C20—C210.0001 (1)
C4—C3—S—N115.3 (2)C18—C19—C20—H20180.0000
C4—C3—S—O12.7 (3)H19—C19—C20—C21180.0000
C4—C3—S—O2134.4 (2)H19—C19—C20—H200.0001 (2)
C3—C4—C5—C614.9 (4)C19—C20—C21—C220.0001 (1)
C3—C4—C5—C8153.4 (3)C19—C20—C21—H21180.0000
H4—C4—C5—C6173 (3)H20—C20—C21—C22180.0000
H4—C4—C5—C819 (3)H20—C20—C21—H210.0001 (2)
C4—C5—C6—C714.2 (5)C20—C21—C22—C170.0001 (1)
C4—C5—C6—H6177 (2)C20—C21—C22—H22180.0000
C8—C5—C6—C7154.0 (3)H21—C21—C22—C17180.0000
C8—C5—C6—H615 (2)H21—C21—C22—H220.0001 (1)
C4—C5—C8—H8138 (2)C17—N—S—C3159.9 (3)
C4—C5—C8—H82155 (2)C17—N—S—O183.3 (3)
C4—C5—C8—C8i81.5 (4)C17—N—S—O245.0 (3)
C6—C5—C8—H81154 (2)Si—N—S—C359.8 (3)
C6—C5—C8—H8237 (2)Si—N—S—O157.0 (3)
C6—C5—C8—C8i86.2 (4)Si—N—S—O2174.7 (2)
Symmetry codes: (i) x+1/2, y, z; (ii) x, y+1/2, z1/2; (iii) x, y1, z; (iv) x+1, y, z+2; (v) x, y+3/2, z+1/2; (vi) x+1, y+1, z+2; (vii) x, y+1/2, z+1/2; (viii) x+1, y+1/2, z+3/2; (ix) x+1/2, y1/2, z+3/2; (x) x, y+1, z; (xi) x+1/2, y+1, z; (xii) x+1/2, y+1/2, z1/2; (xiii) x+1/2, y+1, z+2; (xiv) x, y+3/2, z1/2; (xv) x+1/2, y+3/2, z1/2; (xvi) x1/2, y+1/2, z+3/2; (xvii) x+1, y1/2, z+3/2; (xviii) x1/2, y+1, z+2.

Experimental details

(PCF1)(PCF2)(PCF3)(PCF4)
Crystal data
Chemical formulaC16H15SO3+K.2H2OC16H14S2O5.1/2CH2Cl2C16H15NS2O4.2CH3CNC19H21NS2O4
Mr362.5392.9431.54391.5
Crystal system, space groupMonoclinic, P21/aMonoclinic, C2/cMonoclinic, P21/mOrthorhombic, Pmcn
Temperature (K)213211293293
a, b, c (Å)11.493 (3), 7.685 (1), 18.150 (3)15.927 (2), 7.7031 (4), 26.257 (2)8.725 (7), 10.259 (7), 10.950 (6)10.587 (2), 10.779 (3), 15.644 (5)
α, β, γ (°)90, 91.49 (2), 9090, 98.17 (1), 9090, 92.87 (4), 9090, 90, 90
V3)1602.5 (5)3188.7 (5)979 (1)1785.3 (8)
Z4824
Radiation typeCu KαCu KαMo KαCu Kα
µ (mm1)4.344.800.312.92
Crystal size (mm)1.25 × 0.70 × 0.200.88 × 0.25 × 0.061.00 × 0.35 × 0.250.30 × 0.25 × 0.10
Data collection
DiffractometerENRAF NONIUS CAD4
diffractometer
ENRAF NONIUS CAD4
diffractometer
ENRAF NONIUS CAD4
diffractometer
ENRAF NONIUS CAD4
diffractometer
Absorption correction
No. of measured, independent and
observed [refl observed if I > 2.5 σ(I )] reflections
2709, 2709, 2633 2357, 2357, 2176 2982, 2982, 2011 1939, 1939, 804
Rint0000
θmax (°)64.959.929.974.7
(sin θ/λ)max1)0.5870.5610.7020.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.087, 1.36 0.061, 0.067, 0.98 0.056, 0.064, 0.76 0.089, 0.095, 0.87
No. of reflections263321252011804
No. of parameters269283175125
No. of restraints19151211
H-atom treatmentRidingRidingRidingRiding
(Δ/σ)max0.090.3370.3070.021
Δρmax, Δρmin (e Å3)1.06, 0.660.88, 0.550.55, 0.580.59, 0.49


(PCF5)(PCF6)(PCF7)
Crystal data
Chemical formulaC19H21NS2O4C19H19NS2O4C22H19NS2O4
Mr391.5389.5425.5
Crystal system, space groupOrthorhombic, PbcaOrthorhombic, PbcaOrthorhombic, Pmcn
Temperature (K)293293293
a, b, c (Å)12.845 (2), 15.0121 (7), 18.6430 (8)9.826 (2), 14.632 (2), 23.770 (4)9.915 (2), 12.426 (1), 15.418 (2)
α, β, γ (°)90, 90, 9090, 90, 9090, 90, 90
V3)3594.8 (5)3418 (1)1899.6 (5)
Z884
Radiation typeCu KαMo KαCu Kα
µ (mm1)2.900.342.81
Crystal size (mm)0.50 × 0.40 × 0.400.50 × 0.45 × 0.400.60 × 0.60 × 0.25
Data collection
DiffractometerENRAF NONIUS CAD4
diffractometer
ENRAF NONIUS CAD4
diffractometer
ENRAF NONIUS CAD4
diffractometer
Absorption correction
No. of measured, independent and
observed [refl observed if I > 2.5 σ(I )] reflections
3679, 3679, 3190 4940, 4940, 3089 2069, 2069, 1793
Rint000
θmax (°)74.729.974.7
(sin θ/λ)max1)0.6260.7010.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.069, 0.98 0.046, 0.052, 0.77 0.049, 0.054, 0.86
No. of reflections319030891793
No. of parameters320312185
No. of restraints211912
H-atom treatmentRidingRidingRiding
(Δ/σ)max0.2580.2050.077
Δρmax, Δρmin (e Å3)0.73, 0.890.29, 0.390.39, 0.52

Computer programs: Enraf-Nonius CAD-4 Software, CELCON prog. comparable to xtal_LATCON, xtal_SORTRF (Hall, Spadaccini & Stewart, 1992), xtal_ADDREF (Davenport & Hall, 1992)_SORTRF (Hall, Spadaccini & Stewart, 1992), Xtal, xtal_ADDREF (Davenport & Hall, 1992)_SORTRF_(Hall, Spadaccini & Stewart, 1992), xtal_SIMPEL (Schenk & Hall, 1992), xtal_CRYLSQ (Olthof-Hazekamp, 1992), xtal_ORTEP (Davenport, Hall & Dreissig, 1992), xtal_BONDLA_(Dreissig, Doherty, Stewart & Hall, 1992)_CIFIO_(Hall, 1992).

Selected geometric parameters (Å, º) for (PCF1) top
C1—C21.517 (8)C9—C101.51 (1)
C1—C91.57 (1)C10—C151.40 (1)
C2—C71.390 (9)C10—C111.400 (9)
C2—C31.392 (8)C11—C121.387 (9)
C3—C41.393 (8)C12—C131.394 (9)
C3—S1.786 (6)C13—C141.390 (9)
C4—C51.399 (8)C13—C161.51 (1)
C5—C61.394 (9)C14—C151.381 (9)
C5—C81.514 (9)O1—S1.449 (4)
C6—C71.382 (9)O2—S1.455 (5)
C8—C161.57 (1)O3—S1.437 (5)
C2—C1—C9112.7 (5)C10—C9—C1114.1 (6)
C7—C2—C3115.8 (5)C15—C10—C11116.6 (6)
C7—C2—C1118.3 (5)C15—C10—C9122.5 (6)
C3—C2—C1124.8 (5)C11—C10—C9119.7 (6)
C2—C3—C4121.0 (5)C12—C11—C10120.5 (6)
C2—C3—S121.5 (4)C14—C13—C12116.8 (6)
C4—C3—S117.4 (4)C14—C13—C16120.9 (6)
C6—C5—C4116.7 (5)C12—C13—C16120.8 (6)
C6—C5—C8120.8 (6)C13—C16—C8112.5 (6)
C4—C5—C8121.6 (6)O3—S—C3108.7 (3)
C5—C8—C16113.4 (6)
Selected geometric parameters (Å, º) for (PCF2) top
C1—C21.523 (9)C10—C151.386 (8)
C1—C91.610 (9)C11—C121.403 (8)
C2—C31.377 (7)C11—S21.761 (5)
C2—C71.394 (8)C12—C131.392 (8)
C3—C41.418 (8)C13—C141.368 (8)
C3—S11.750 (5)C13—C161.523 (9)
C4—C51.396 (8)C14—C151.403 (9)
C5—C61.372 (8)S1—O21.402 (4)
C5—C81.528 (9)S1—O11.436 (5)
C6—C71.398 (9)S1—O31.657 (4)
C8—C161.594 (9)S2—O41.403 (4)
C9—C101.526 (9)S2—O51.431 (5)
C10—C111.383 (7)S2—O31.640 (4)
C2—C1—C9112.2 (5)C11—C10—C9123.5 (5)
C3—C2—C7116.3 (5)C15—C10—C9119.2 (5)
C3—C2—C1124.6 (5)C10—C11—C12122.1 (5)
C7—C2—C1118.1 (5)C10—C11—S2122.3 (4)
C2—C3—C4121.8 (5)C12—C11—S2115.4 (4)
C2—C3—S1122.0 (4)C14—C13—C12118.0 (5)
C4—C3—S1115.5 (4)C14—C13—C16121.6 (5)
C6—C5—C4118.2 (5)C12—C13—C16119.4 (5)
C6—C5—C8121.1 (5)C13—C16—C8112.1 (5)
C4—C5—C8119.6 (5)O3—S1—C3101.8 (2)
C5—C8—C16112.4 (5)O3—S2—C11103.5 (2)
C10—C9—C1112.6 (5)S2—O3—S1126.2 (3)
C11—C10—C15116.0 (5)
Selected geometric parameters (Å, º) for (PCF3) top
C1—C21.513 (5)C5—C61.393 (6)
C1—C1i1.613 (5)C5—C81.519 (6)
C2—C71.396 (5)C6—C71.387 (6)
C2—C31.409 (5)C8—C8i1.610 (7)
C3—C41.395 (5)S1—O11.426 (3)
C3—S11.767 (4)S1—O21.435 (3)
C4—C51.396 (5)S1—N1.664 (2)
C2—C1—C1i112.4 (3)C6—C5—C4117.4 (3)
C7—C2—C3115.6 (3)C6—C5—C8121.7 (3)
C7—C2—C1119.0 (3)C4—C5—C8119.9 (4)
C3—C2—C1124.3 (3)C5—C8—C8i112.1 (3)
C4—C3—C2121.6 (3)N—S1—C3105.8 (2)
C4—C3—S1116.7 (3)S1i—N—S1126.4 (3)
C2—C3—S1121.3 (2)
Symmetry code: (i) x, y+3/2, z.
Selected geometric parameters (Å, º) for (PCF4) top
C1i—C2i1.512 (15)C5i—C8i1.532 (16)
C1i—C1ii1.558 (16)C6i—C7i1.392 (15)
C2i—C7i1.398 (15)C8i—C8ii1.504 (18)
C2i—C3i1.439 (15)Ni—Sii1.676 (7)
C3i—C4i1.390 (16)Ni—Si1.676 (7)
C3i—Si1.756 (11)Si—O1i1.434 (8)
C4i—C5i1.402 (16)Si—O2i1.441 (9)
C5i—C6i1.407 (16)
C2i—C1i—C1ii113.5 (9)C4i—C5i—C6i117.9 (11)
C7i—C2i—C3i114.0 (10)C4i—C5i—C8i119.4 (10)
C7i—C2i—C1i120.6 (9)C6i—C5i—C8i120.7 (10)
C3i—C2i—C1i123.5 (9)C8ii—C8i—C5i114.2 (9)
C4i—C3i—C2i122.9 (9)Sii—Ni—Si122.8 (8)
C4i—C3i—Si117.0 (7)Ni—Si—C3i104.7 (6)
C2i—C3i—Si119.9 (8)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1/2, y+1/2, z1/2.
Selected geometric parameters (Å, º) for (PCF5) top
C1—C21.505 (7)C8—C161.597 (9)
C1—C91.604 (7)C9—C101.512 (7)
C2—C71.388 (7)C10—C151.374 (7)
C2—C31.411 (6)C10—C111.416 (6)
C3—C41.384 (6)C11—C121.376 (6)
C3—S11.765 (4)C11—S21.764 (4)
C4—C51.381 (7)C12—C131.386 (6)
C5—C61.410 (7)C13—C141.400 (7)
C5—C81.495 (7)C13—C161.496 (7)
C6—C71.360 (8)C14—C151.371 (7)
C2—C1—C9112.2 (4)C15—C10—C9120.1 (4)
C7—C2—C3114.3 (4)C11—C10—C9123.4 (4)
C7—C2—C1120.5 (4)C12—C11—C10121.5 (4)
C3—C2—C1124.2 (4)C12—C11—S2117.0 (3)
C4—C3—C2121.7 (4)C10—C11—S2121.4 (3)
C4—C3—S1116.6 (3)C12—C13—C14116.6 (4)
C2—C3—S1121.6 (3)C12—C13—C16120.8 (5)
C4—C5—C6116.0 (5)C14—C13—C16121.6 (4)
C4—C5—C8121.5 (4)C13—C16—C8112.6 (4)
C6—C5—C8121.0 (5)S1—N—S2119.2 (2)
C5—C8—C16112.2 (4)N—S1—C3105.5 (2)
C10—C9—C1111.7 (4)N—S2—C11105.4 (2)
C15—C10—C11115.0 (4)
Selected geometric parameters (Å, º) for (PCF6) top
C1—C21.491 (5)C10—C111.421 (5)
C1—C91.592 (6)C11—C121.382 (5)
C2—C71.401 (5)C11—S21.774 (3)
C2—C31.412 (4)C12—C131.390 (5)
C3—C41.395 (5)C13—C141.389 (6)
C3—S11.753 (3)C13—C161.515 (6)
C4—C51.397 (5)C14—C151.384 (6)
C5—C61.383 (5)N—S21.686 (3)
C5—C81.512 (5)N—S11.693 (3)
C6—C71.387 (6)O1—S11.426 (3)
C8—C161.582 (6)O2—S11.433 (3)
C9—C101.501 (5)O4—S21.428 (3)
C10—C151.405 (5)O5—S21.438 (3)
C2—C1—C9112.5 (3)C15—C10—C9119.9 (3)
C7—C2—C3114.2 (3)C11—C10—C9124.2 (3)
C7—C2—C1120.7 (3)C12—C11—C10122.8 (3)
C3—C2—C1123.9 (3)C12—C11—S2116.0 (2)
C4—C3—C2122.2 (3)C10—C11—S2121.2 (2)
C4—C3—S1116.6 (2)C14—C13—C12117.6 (4)
C2—C3—S1121.1 (2)C14—C13—C16121.5 (4)
C6—C5—C4116.8 (3)C12—C13—C16119.4 (3)
C6—C5—C8122.1 (3)C13—C16—C8112.2 (3)
C4—C5—C8120.0 (3)S2—N—S1124.4 (2)
C5—C8—C16112.2 (3)N—S1—C3105.0 (1)
C10—C9—C1112.4 (3)N—S2—C11106.6 (1)
C15—C10—C11114.0 (3)
Selected geometric parameters (Å, º) for (PCF7) top
C1—C21.511 (5)C5—C81.508 (5)
C1—C1i1.608 (4)C6—C71.385 (5)
C2—C71.393 (5)C8—C8i1.583 (6)
C2—C31.401 (4)N—Si1.705 (2)
C3—C41.396 (4)N—S1.705 (2)
C3—S1.759 (3)S—O11.426 (2)
C4—C51.389 (5)S—O21.435 (3)
C5—C61.388 (5)
C2—C1—C1i112.1 (3)C6—C5—C4117.0 (3)
C7—C2—C3115.3 (3)C6—C5—C8121.5 (3)
C7—C2—C1119.3 (3)C4—C5—C8120.5 (3)
C3—C2—C1124.2 (3)C5—C8—C8i112.6 (3)
C4—C3—C2121.9 (3)Si—N—S122.8 (2)
C4—C3—S116.4 (2)N—S—C3104.4 (2)
C2—C3—S121.6 (2)
Symmetry code: (i) x+1/2, y, z.
 

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