Influence of aromatic sulfonation on the geometry of [2.2]paracyclophane: crystal structures of one sulfonate, one disulfonic anhydride and five ­disulfonimides

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[8.2.2.2^4,7]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.

S1. Experimental

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

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

(PCF1) potassium [2.2]paracyclophane-4-sulfonate

Crystal data

C16H15SO3^+K^−.2H2O	F(000) = 760
Mr = 362.5	Dx = 1.50 Mg m^−3
Monoclinic, P21/a	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yab	Cell parameters from 23 reflections
a = 11.493 (3) Å	θ = 39.9–42.8°
b = 7.685 (1) Å	µ = 4.34 mm^−1
c = 18.150 (3) Å	T = 213 K
β = 91.49 (2)°	Rod, colourless
V = 1602.5 (5) Å^3	1.25 × 0.70 × 0.20 mm
Z = 4

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 64.9°, θmin = 4.9°
Graphite monochromator	h = 0→13
θ/2θ scans	k = 0→9
2709 measured reflections	l = −21→21
2709 independent reflections	2 standard reflections every 60 min
2633 reflections with refl observed if I > 2.5 σ(I )	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	Riding
R[F^2 > 2σ(F^2)] = 0.086	1/[5.9 + 0.0038*σ(Fobs)^2 + 0.00002/σ(Fobs)]
wR(F^2) = 0.087	(Δ/σ)max = 0.09
S = 1.36	Δρmax = 1.06 e Å^−3
2633 reflections	Δρmin = −0.66 e Å^−3
269 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
19 restraints	Extinction coefficient: 264 (75)

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0556 (5)	0.8953 (9)	0.6988 (3)	0.038 (3)
C2	0.1719 (5)	0.8550 (8)	0.7365 (3)	0.033 (3)
C3	0.2766 (5)	0.9362 (7)	0.7207 (3)	0.030 (3)
C4	0.3635 (5)	0.9574 (8)	0.7748 (3)	0.031 (3)
C5	0.3496 (5)	0.8887 (8)	0.8454 (3)	0.037 (3)
C6	0.2598 (6)	0.7689 (8)	0.8536 (3)	0.040 (3)
C7	0.1725 (5)	0.7544 (8)	0.8002 (4)	0.037 (3)
C8	0.4129 (6)	0.965 (1)	0.9122 (4)	0.046 (4)
C9	−0.0114 (6)	1.047 (1)	0.7376 (4)	0.053 (4)
C10	0.0497 (5)	1.1166 (9)	0.8061 (4)	0.042 (4)
C11	0.1409 (6)	1.2360 (8)	0.7996 (4)	0.041 (4)
C12	0.2270 (5)	1.2486 (9)	0.8543 (4)	0.041 (3)
C13	0.2249 (6)	1.1431 (9)	0.9167 (3)	0.041 (3)
C14	0.1213 (6)	1.0565 (9)	0.9298 (4)	0.042 (4)
C15	0.0353 (6)	1.0427 (9)	0.8756 (4)	0.042 (4)
C16	0.3362 (6)	1.093 (1)	0.9574 (4)	0.051 (4)
O1	0.4241 (4)	1.0717 (6)	0.6314 (2)	0.042 (2)
O2	0.2729 (4)	0.8886 (6)	0.5803 (2)	0.045 (3)
O3	0.2280 (4)	1.1776 (6)	0.6222 (2)	0.046 (3)
S	0.3015 (1)	1.0278 (2)	0.63207 (7)	0.0310 (7)
K	0.4391 (1)	0.7674 (2)	0.48204 (8)	0.0394 (8)
O1s	0.3747 (4)	0.4534 (6)	0.5453 (2)	0.044 (3)
O2s	0.6165 (4)	0.9073 (6)	0.5721 (2)	0.046 (3)
H101	0.005 (5)	0.790 (5)	0.694 (4)	0.05 (2)*
H102	0.060 (5)	0.942 (7)	0.648 (1)	0.04 (2)*
H4	0.431 (3)	1.035 (6)	0.764 (3)	0.02 (1)*
H6	0.256 (4)	0.707 (6)	0.902 (2)	0.02 (1)*
H7	0.106 (4)	0.673 (7)	0.807 (3)	0.05 (2)*
H81	0.436 (5)	0.873 (6)	0.949 (2)	0.03 (2)*
H82	0.488 (4)	1.02 (1)	0.900 (4)	0.08 (3)*
H91	−0.021 (7)	1.143 (7)	0.701 (3)	0.08 (3)*
H92	−0.093 (3)	1.009 (9)	0.747 (4)	0.06 (2)*
H11	0.151 (5)	1.299 (7)	0.752 (2)	0.03 (2)*
H12	0.295 (4)	1.326 (7)	0.847 (4)	0.05 (2)*
H14	0.117 (5)	0.994 (6)	0.978 (2)	0.02 (1)*
H15	−0.036 (3)	0.977 (7)	0.889 (3)	0.05 (2)*
H161	0.325 (5)	1.036 (7)	1.006 (2)	0.04 (2)*
H162	0.379 (6)	1.197 (6)	0.977 (4)	0.06 (2)*
H11s	0.35326	0.39502	0.59228	0.08000*
H12s	0.33034	0.37902	0.51139	0.08000*
H21s	0.58084	0.98246	0.60818	0.15000*
H22s	0.68328	0.88027	0.60527	0.08000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.033 (3)	0.043 (4)	0.036 (3)	−0.008 (3)	−0.001 (3)	0.001 (3)
C2	0.036 (3)	0.031 (3)	0.034 (3)	−0.001 (3)	0.005 (2)	−0.009 (3)
C3	0.037 (3)	0.027 (3)	0.025 (3)	0.002 (2)	0.007 (2)	0.001 (2)
C4	0.031 (3)	0.029 (3)	0.033 (3)	0.001 (2)	0.003 (2)	0.000 (2)
C5	0.032 (3)	0.039 (3)	0.041 (3)	0.011 (3)	0.003 (3)	0.001 (3)
C6	0.048 (4)	0.037 (4)	0.035 (3)	0.010 (3)	0.010 (3)	0.011 (3)
C7	0.039 (3)	0.030 (3)	0.044 (4)	−0.004 (3)	0.011 (3)	0.001 (3)
C8	0.045 (4)	0.058 (5)	0.034 (3)	0.005 (3)	−0.004 (3)	0.002 (3)
C9	0.041 (4)	0.065 (5)	0.053 (4)	0.010 (4)	−0.012 (3)	−0.006 (4)
C10	0.033 (3)	0.041 (4)	0.052 (4)	0.012 (3)	0.006 (3)	−0.005 (3)
C11	0.047 (4)	0.034 (3)	0.043 (4)	0.014 (3)	0.010 (3)	0.005 (3)
C12	0.037 (3)	0.035 (3)	0.050 (4)	−0.003 (3)	0.011 (3)	−0.007 (3)
C13	0.042 (4)	0.043 (4)	0.037 (3)	0.005 (3)	0.004 (3)	−0.015 (3)
C14	0.050 (4)	0.038 (4)	0.039 (3)	0.007 (3)	0.011 (3)	0.001 (3)
C15	0.037 (3)	0.036 (4)	0.052 (4)	0.001 (3)	0.010 (3)	−0.002 (3)
C16	0.053 (4)	0.059 (5)	0.040 (4)	0.007 (4)	−0.004 (3)	−0.012 (4)
O1	0.039 (2)	0.048 (3)	0.040 (2)	−0.000 (2)	0.008 (2)	0.008 (2)
O2	0.050 (3)	0.052 (3)	0.032 (2)	−0.007 (2)	0.005 (2)	0.001 (2)
O3	0.049 (3)	0.050 (3)	0.039 (2)	0.004 (2)	0.002 (2)	0.009 (2)
S	0.0327 (7)	0.0332 (8)	0.0273 (7)	−0.0016 (6)	0.0018 (5)	0.0023 (6)
K	0.0354 (7)	0.0352 (8)	0.0476 (8)	−0.0012 (6)	−0.0012 (6)	0.0035 (6)
O1s	0.041 (2)	0.039 (3)	0.053 (3)	−0.002 (2)	0.001 (2)	0.009 (2)
O2s	0.049 (3)	0.043 (3)	0.047 (3)	0.006 (2)	0.006 (2)	0.005 (2)

Geometric parameters (Å, º)

C1—H101	1.00 (5)	C10—C11	1.400 (9)
C1—H102	1.00 (3)	C11—H11	1.00 (4)
C1—C2	1.517 (8)	C11—C12	1.387 (9)
C1—C9	1.57 (1)	C12—H12	1.00 (5)
C2—C7	1.390 (9)	C12—C13	1.394 (9)
C2—C3	1.392 (8)	C13—C14	1.390 (9)
C3—C4	1.393 (8)	C13—C16	1.51 (1)
C3—S	1.786 (6)	C14—H14	1.00 (3)
C4—H4	1.00 (4)	C14—C15	1.381 (9)
C4—C5	1.399 (8)	C15—H15	1.00 (5)
C5—C6	1.394 (9)	C16—H162	1.00 (5)
C5—C8	1.514 (9)	C16—H161	1.00 (4)
C6—H6	1.00 (3)	O1—S	1.449 (4)
C6—C7	1.382 (9)	O2—S	1.455 (5)
C7—H7	1.00 (5)	O2—K	2.806 (5)
C8—H82	1.00 (5)	O3—S	1.437 (5)
C8—H81	1.00 (4)	K—O1s	2.781 (4)
C8—C16	1.57 (1)	K—O2s	2.795 (4)
C9—H91	1.00 (6)	O1s—H12s	0.974 (4)
C9—H92	1.00 (4)	O1s—H11s	0.999 (4)
C9—C10	1.51 (1)	O2s—H21s	0.971 (4)
C10—C15	1.40 (1)	O2s—H22s	0.984 (4)
H21s···H22s	1.4174 (3)	O1s···O1s^x	3.430 (6)
H11s···H12s	1.4899 (2)	K···H102^xiv	3.43 (5)
H161···H162	1.49 (8)	C12···H92^vi	3.43 (6)
H81···H82	1.57 (9)	C3···C9	3.439 (9)
H91···H92	1.57 (9)	H91···H12^vii	3.44 (9)
H101···H102	1.58 (7)	S···H22s^iv	3.447 (1)
O1···H21s	1.984 (4)	C8···C14	3.45 (1)
C9···H102	2.02 (4)	O3···H22s^vii	3.449 (5)
O2···H12s^i	2.021 (4)	O2···O2s^xiii	3.452 (6)
C13···H14	2.04 (5)	S···H91^vi	3.46 (7)
C14···H15	2.04 (4)	C3···C12	3.470 (9)
C2···H7	2.05 (6)	O3···H91^vi	3.47 (7)
C5···H6	2.05 (5)	C14···H15^viii	3.47 (6)
C16···H81	2.05 (5)	C10···H7	3.47 (5)
H102···H91	2.06 (8)	C8···H15^ix	3.47 (6)
C10···H91	2.06 (6)	H102···H11	3.48 (7)
C12···H11	2.07 (4)	H101···H11s^iv	3.48 (5)
C3···H4	2.07 (4)	C12···H15^vi	3.48 (5)
C13···H12	2.07 (6)	C14···H162^vii	3.49 (6)
C11···H12	2.07 (5)	C4···C16	3.496 (9)
C6···H7	2.07 (5)	S···H12s^ii	3.497 (1)
C8···H161	2.08 (4)	O1s···O2s^x	3.500 (6)
C10···H11	2.08 (5)	H7···H12^xii	3.50 (7)
C5···H4	2.09 (5)	S···H11	3.50 (5)
C7···H6	2.09 (3)	O1···H11^vi	3.51 (5)
H81···H161	2.09 (7)	C6···H161	3.51 (4)
C15···H14	2.09 (4)	H161···H162^iii	3.52 (8)
C13···H162	2.10 (6)	C14···H6^xi	3.53 (4)
C1···H91	2.10 (6)	C7···H92^ix	3.53 (5)
C5···H81	2.10 (5)	C7···H82^iv	3.53 (7)
C10···H92	2.11 (5)	H4···H92^vi	3.53 (8)
C2···H101	2.11 (6)	H81···H14^ix	3.54 (7)
C10···H15	2.11 (6)	H6···H82^iv	3.54 (7)
C5···H82	2.11 (6)	S···H101^ix	3.55 (5)
C1···H92	2.12 (5)	H91···H21s^vii	3.55 (6)
C13···H161	2.13 (4)	O3···O2s^vii	3.547 (6)
C16···H82	2.13 (6)	C6···H162^iii	3.55 (7)
C9···H101	2.14 (5)	C12···H82	3.55 (5)
C2···H102	2.14 (4)	H12···H14^xi	3.55 (7)
C8···H162	2.18 (5)	H12s···H21s^iv	3.5643 (6)
H101···H92	2.25 (8)	H4···H81	3.57 (7)
O3···H11s^ii	2.280 (5)	C4···O3	3.569 (7)
H82···H162	2.33 (9)	C8···H82^v	3.57 (7)
H6···H161^iii	2.34 (6)	C9···O1^vii	3.573 (9)
C3···C7	2.356 (8)	C13···H81^xi	3.57 (5)
O2···H22s^iv	2.358 (5)	H92···H11	3.58 (7)
H14···H15	2.37 (7)	H102···H7	3.58 (7)
H11···H12	2.37 (7)	O1···K	3.588 (5)
C12···C14	2.371 (9)	H82···H11^vi	3.59 (8)
C4···C6	2.377 (9)	H14···H161^iii	3.59 (7)
C11···C15	2.380 (9)	C5···H101^ix	3.60 (6)
O1···O3	2.397 (6)	C4···H11	3.60 (5)
O1···O2	2.402 (6)	O2···H101^ix	3.60 (6)
C5···C7	2.408 (9)	H7···H92	3.60 (8)
O2···O3	2.408 (7)	O1s···H102^xiv	3.60 (3)
C13···C15	2.412 (9)	C7···H4^iv	3.60 (4)
C10···C14	2.417 (9)	H6···H82	3.60 (8)
H6···H7	2.42 (7)	K···H91^xiv	3.60 (6)
C11···C13	2.419 (9)	O2···O1s	3.605 (6)
C10···C12	2.420 (9)	O3···H4	3.60 (4)
C2···C6	2.421 (8)	C5···H92^ix	3.61 (7)
C3···C5	2.422 (8)	C4···H91^vi	3.61 (6)
C2···C4	2.423 (8)	C7···H11^xii	3.62 (5)
H14···H162^iii	2.42 (7)	C14···H82^vii	3.62 (7)
O1···H4	2.43 (5)	C2···H21s^iv	3.622 (6)
H91···H11s^iv	2.43 (7)	H14···H162^vii	3.62 (8)
H14···H161	2.44 (8)	C1···O1s^iv	3.625 (7)
H91···H11	2.47 (9)	H7···H161^iii	3.62 (7)
C1···C7	2.496 (9)	O1s···H21s^iv	3.626 (4)
H101···H7	2.50 (8)	O1s···H101^ix	3.63 (6)
C9···C11	2.52 (1)	O2···H21s	3.634 (4)
C14···C16	2.52 (1)	C8···H14	3.64 (5)
C12···C16	2.53 (1)	C12···H6^ii	3.64 (5)
H4···H82	2.53 (9)	C12···H7^ii	3.64 (5)
C6···C8	2.53 (1)	C9···O3	3.641 (9)
C4···C8	2.543 (9)	C15···H6	3.64 (5)
H81···H162^v	2.55 (8)	K···H11s	3.643 (1)
C9···C15	2.55 (1)	C2···O2s^iv	3.643 (7)
H12···H15^vi	2.55 (7)	K···H22s	3.647 (1)
C8···C13	2.56 (1)	O2···H21s^iv	3.650 (5)
H6···H81	2.57 (7)	K···H102^ix	3.65 (4)
C3···O2	2.573 (7)	C15···H81^iv	3.66 (5)
C2···C9	2.57 (1)	C4···H92^ix	3.66 (7)
C5···C16	2.58 (1)	O3···O1s^i	3.664 (6)
C1···C3	2.579 (8)	C11···H102	3.67 (4)
C1···C10	2.587 (9)	C5···C11	3.669 (9)
H92···H12^vii	2.59 (9)	C7···H12^xii	3.67 (5)
C3···O1	2.594 (7)	O1s···H92^ix	3.68 (7)
O1···H91^vi	2.60 (6)	C1···H15	3.68 (6)
H102···H92	2.60 (7)	C6···C10	3.688 (9)
H11s···H22s^iv	2.6226 (4)	C7···H22s^iv	3.691 (6)
C3···O3	2.626 (7)	C4···O2	3.692 (7)
H81···H162	2.63 (7)	C9···O1s^iv	3.696 (9)
H14···H15^viii	2.63 (7)	C7···C13	3.700 (9)
C11···H91	2.64 (7)	C14···H7	3.70 (6)
H92···H15	2.65 (9)	C6···C12	3.706 (9)
C1···H7	2.65 (6)	C8···C16^v	3.71 (1)
H7···H82^iv	2.66 (9)	O1···O2s^xiii	3.715 (6)
C16···H14	2.66 (5)	C7···C11	3.718 (9)
H4···H7^ix	2.67 (6)	K···H11s^i	3.720 (2)
C8···H6	2.68 (5)	C16···H4	3.72 (5)
C14···H161	2.69 (5)	C5···H14	3.73 (4)
O3···H102	2.69 (6)	C7···H92	3.73 (5)
C4···H82	2.70 (7)	C4···H7	3.74 (5)
C9···H11	2.70 (6)	S···O1s^ii	3.736 (4)
O3···H11	2.70 (4)	C7···H4	3.74 (4)
O1···H11s^ii	2.704 (5)	C1···C6	3.741 (9)
C7···H101	2.70 (6)	C12···H15	3.74 (5)
H12···H162	2.70 (9)	C3···H6	3.74 (3)
C16···H12	2.72 (6)	C15···H12	3.74 (5)
C4···S	2.724 (6)	C11···H4	3.74 (4)
H82···H161	2.73 (8)	C11···H14	3.75 (4)
H6···H162^iii	2.73 (8)	C13···H14^xi	3.75 (5)
H101···H91	2.74 (7)	C2···C12	3.748 (9)
C4···C7	2.742 (8)	C15···C16	3.75 (1)
C15···H92	2.74 (6)	C14···H11	3.75 (4)
C3···C6	2.744 (8)	C9···C12	3.75 (1)
C8···H4	2.75 (5)	C7···C8	3.754 (9)
C12···C15	2.748 (9)	C11···C16	3.76 (1)
O2s···H12s^x	2.750 (4)	C13···H82^vii	3.76 (6)
C11···C14	2.750 (9)	C8···C8^v	3.759 (9)
C6···H81	2.75 (5)	C3···H92^ix	3.76 (7)
H82···H161^v	2.75 (8)	S···K	3.761 (2)
H101···H21s^iv	2.76 (5)	C9···C14	3.77 (1)
C5···C13	2.765 (9)	C13···H4	3.78 (5)
C2···C10	2.775 (9)	C15···H6^iv	3.78 (5)
C2···S	2.779 (6)	C3···H12	3.78 (6)
O1···O2s	2.788 (6)	C3···H91	3.78 (8)
H6···H15^ix	2.79 (7)	C1···C4^iv	3.780 (9)
C3···H102	2.79 (5)	C11···H92^vi	3.78 (5)
O1s···H22s^iv	2.789 (4)	C7···H14	3.78 (4)
H4···H91^vi	2.79 (7)	C3···C8	3.781 (8)
O2···H102	2.79 (5)	C1···C4	3.794 (8)
S···H4	2.79 (5)	O1s···H12s^x	3.794 (4)
C10···C13	2.814 (9)	O1s···H22s^x	3.794 (4)
C9···H15	2.81 (6)	S···O1s^i	3.802 (4)
C2···C5	2.817 (8)	O2s···H11s^x	3.805 (4)
C12···H162	2.82 (7)	C1···H4^iv	3.81 (4)
O3···H12s^ii	2.820 (4)	C2···H15	3.82 (5)
H14···H14^viii	2.84 (7)	O2···H101	3.82 (6)
H102···H11s^iv	2.85 (6)	C6···H15	3.83 (4)
C4···O1	2.851 (7)	C4···H11^vi	3.83 (6)
O2···O1s^i	2.851 (6)	C16···H15^vi	3.83 (6)
H4···H11^vi	2.85 (7)	C15···H101	3.84 (6)
S···H102	2.87 (6)	O1···H92^vi	3.85 (7)
K···H12s^x	2.878 (1)	O2···H22s^xiii	3.853 (4)
O2···O2s^iv	2.900 (6)	C5···C15	3.854 (9)
O1s···H102^ix	2.90 (5)	O3···H92^vi	3.86 (6)
H12s···H22s^x	2.9088 (3)	C4···C10	3.864 (8)
C16···H6^xi	2.93 (4)	C6···C16^iii	3.87 (1)
H81···H15^ix	2.93 (7)	S···K^i	3.877 (2)
C4···H101^ix	2.93 (5)	C15···H162^iii	3.88 (6)
H81···H161^v	2.93 (8)	S···O2s^xiii	3.880 (4)
H101···H22s^iv	2.94 (6)	C2···O1	3.886 (7)
H101···H4^iv	2.95 (6)	C14···H81	3.89 (5)
H92···H11s^iv	2.95 (7)	C2···H92^ix	3.89 (6)
H102···H22s^iv	2.97 (6)	C2···C14	3.893 (9)
C15···H12^vii	2.97 (5)	C7···H161^iii	3.90 (4)
H81···H82^v	2.97 (9)	K···O1s^i	3.899 (4)
S···H11s^ii	2.977 (1)	C12···C15^vi	3.899 (9)
O2s···H101^ix	2.99 (6)	O2···H11s	3.909 (5)
C2···H22s^iv	2.996 (6)	K···H22s^iv	3.909 (1)
C4···H7^ix	3.01 (5)	C14···H161^xi	3.91 (5)
K···H11s^x	3.040 (1)	C5···C10	3.915 (9)
H81···H81^v	3.04 (7)	S···O2s	3.919 (5)
C11···H4^vii	3.04 (4)	K···H101^ix	3.92 (6)
H12s···H22s^iv	3.0548 (3)	C14···C14^viii	3.922 (9)
C9···H11s^iv	3.060 (7)	C4···C7^ix	3.923 (8)
C7···C15	3.063 (9)	O2···H4	3.93 (5)
C6···H15^ix	3.06 (5)	C15···C16^vii	3.93 (1)
O3···O1s^ii	3.067 (6)	C16···H161^xi	3.93 (6)
H6···H14^iii	3.07 (6)	C11···S	3.938 (7)
C10···H12^vii	3.07 (5)	O2···K^i	3.944 (5)
H6···H14	3.07 (7)	C4···C10^vi	3.944 (9)
C6···C14	3.074 (9)	C6···H82^iv	3.95 (6)
C5···H7^ix	3.09 (5)	C14···H81^iv	3.95 (5)
H7···H11^xii	3.09 (7)	C6···H14^iii	3.95 (4)
O2s···H102^ix	3.09 (5)	C6···C11	3.955 (9)
C16···H81^v	3.09 (5)	C3···C13	3.955 (8)
C10···H4^vii	3.09 (4)	O2···O2s	3.958 (6)
C2···O2	3.102 (7)	O2s···O2s^xiii	3.962 (6)
C1···H22s^iv	3.107 (6)	C7···C12	3.968 (9)
C4···C12	3.109 (9)	C12···H14^xi	3.97 (4)
C5···C12	3.110 (9)	C10···C12^vii	3.970 (9)
O3···H21s^vii	3.119 (5)	C5···C15^ix	3.973 (9)
H6···H12^xii	3.12 (7)	C10···H162^vii	3.98 (7)
C7···C10	3.124 (9)	O2···H21s^xiii	3.977 (4)
C6···C13	3.125 (9)	C5···C7^ix	3.977 (9)
O2s···H11s^ix	3.129 (4)	C4···H21s	3.977 (6)
O1s···H91^ix	3.13 (6)	C4···C11^vi	3.980 (9)
O1···H101^ix	3.13 (5)	C6···C15^ix	3.982 (9)
H4···H12	3.14 (7)	O2s···H11^vi	3.98 (4)
H15···H162^vii	3.14 (8)	C2···C13	3.983 (9)
C5···H161	3.15 (4)	C10···O3	3.989 (8)
C3···C11	3.148 (9)	C15···H4^vii	3.99 (4)
C14···H6	3.15 (5)	O1···O3^vi	3.996 (6)
C8···H7^ix	3.15 (5)	S···K^xiii	3.997 (2)
H82···H162^v	3.17 (9)	C7···H81^iv	4.00 (5)
C11···H82^vii	3.17 (7)	C7···C11^xii	4.001 (9)
C2···C11	3.167 (9)	C3···H91^vi	4.00 (7)
C9···H12^vii	3.18 (6)	O2···H11s^ii	4.004 (5)
O2s···H12s^ix	3.177 (4)	C12···H91	4.01 (7)
C10···H102	3.18 (3)	C6···C12^xii	4.016 (9)
C13···H82	3.19 (5)	O2···O3^xiv	4.018 (6)
C2···H91	3.19 (7)	C7···S	4.019 (7)
S···H12s^i	3.190 (1)	C7···C8^iv	4.024 (9)
C5···H15^ix	3.19 (6)	C15···H161	4.03 (5)
H11···H21s^vii	3.19 (4)	C9···C12^vii	4.04 (1)
C3···H11	3.19 (5)	S···H91	4.04 (8)
C3···H101^ix	3.20 (5)	C5···S	4.041 (6)
O1s···O2s^iv	3.203 (6)	S···H101	4.04 (5)
C8···C12	3.21 (1)	O3···O2s^xiii	4.049 (6)
H102···H12s^i	3.21 (3)	C7···C12^xii	4.055 (9)
K···H12s^i	3.219 (2)	C1···O1^iv	4.071 (8)
C15···H7	3.22 (5)	C8···C11^vi	4.07 (1)
K···H21s	3.230 (1)	C14···C15^viii	4.077 (9)
C4···H12	3.23 (6)	C4···C14	4.080 (9)
C6···C16	3.23 (1)	C3···C15	4.083 (9)
C13···H81	3.23 (5)	C8···C10^vi	4.08 (1)
C15···H14^viii	3.24 (4)	S···O2s^iv	4.094 (5)
H7···H15	3.24 (8)	C8···C15^vi	4.10 (1)
C14···H162^iii	3.24 (5)	C9···S	4.120 (8)
O3···H91	3.24 (8)	C1···C3^iv	4.124 (9)
C3···H7	3.25 (5)	C14···C16^iii	4.13 (1)
C14···H162	3.25 (6)	C4···C9^vi	4.13 (1)
H6···H161	3.25 (6)	C11···O1^vii	4.162 (8)
C12···H14	3.25 (4)	C3···O2s^iv	4.167 (7)
C16···H6	3.27 (5)	C9···O3^vii	4.184 (9)
C1···S	3.266 (6)	C6···C9^ix	4.19 (1)
C10···H101	3.27 (5)	C4···C9^ix	4.20 (1)
C8···H81^v	3.27 (5)	C10···O1^vii	4.199 (8)
C4···H6	3.27 (4)	C8···C15^ix	4.21 (1)
S···H21s	3.270 (2)	C5···C9^ix	4.22 (1)
C14···H12	3.27 (5)	C13···C16^xi	4.22 (1)
C7···C9	3.27 (1)	C1···C5^iv	4.217 (9)
H81···H14^iii	3.27 (6)	C10···C16	4.24 (1)
C1···O3	3.272 (8)	C8···C11	4.24 (1)
C2···H92	3.27 (4)	C5···O1	4.239 (7)
C14···H14^viii	3.27 (5)	C9···C13	4.25 (1)
C15···H162^vii	3.28 (6)	C1···C5	4.246 (8)
C6···H161^iii	3.28 (4)	C12···O3	4.247 (8)
K···H12s	3.285 (1)	C2···C8	4.253 (9)
C6···H4	3.29 (4)	C7···C16	4.27 (1)
H11s···H21s^iv	3.2893 (8)	C8···C14^iii	4.28 (1)
C13···H15	3.29 (4)	C14···C16^vii	4.28 (1)
C15···H11	3.29 (5)	C6···C13^iii	4.279 (9)
H7···H81^iv	3.29 (8)	C16···C16^v	4.28 (1)
C8···H12	3.29 (6)	S···H92^vi	4.28 (7)
H92···H11^vii	3.30 (7)	C4···C15	4.285 (9)
C11···H15	3.30 (5)	C6···C9	4.29 (1)
C2···O3	3.307 (7)	C8···C13^iii	4.30 (1)
C2···H4	3.31 (4)	K···O2s^iv	4.306 (5)
C4···H81	3.31 (5)	C7···O2	4.307 (8)
C13···H11	3.31 (4)	C1···K^iv	4.309 (6)
C6···H14	3.31 (4)	C9···S^vii	4.330 (8)
C15···H91	3.31 (6)	O3···K^xiii	4.333 (5)
C5···H7	3.31 (5)	C3···C14	4.336 (9)
C10···H12	3.32 (5)	C10···C16^vii	4.35 (1)
C9···H4^vii	3.32 (4)	C1···C12	4.350 (9)
C11···H92	3.32 (5)	C2···C4^iv	4.352 (8)
C12···H4	3.32 (4)	C7···O2s^iv	4.353 (8)
C1···C11	3.326 (9)	K···H11^xiv	4.35 (3)
C2···H6	3.33 (3)	C1···K^i	4.355 (7)
C8···H161^v	3.33 (5)	O2···K^iv	4.357 (5)
C10···H14	3.33 (3)	O3···O1s^iv	4.377 (6)
C8···H162^v	3.33 (6)	C8···C12^vi	4.38 (1)
C5···C14	3.332 (9)	K···K^x	4.385 (2)
C16···H14^xi	3.33 (5)	C13···C15^vi	4.387 (9)
C13···H6^xi	3.33 (3)	C10···S	4.392 (7)
C2···C15	3.336 (9)	C8···C14^vi	4.40 (1)
C3···H101	3.34 (5)	C4···C9	4.398 (9)
C1···O2	3.338 (8)	C12···C16^xi	4.40 (1)
C10···H82^vii	3.34 (8)	O2···K^xiii	4.406 (5)
H82···H12	3.35 (8)	C8···C15	4.413 (9)
C7···H102	3.35 (4)	C1···C14	4.418 (9)
C6···H82	3.35 (6)	C6···C11^xii	4.420 (9)
H102···H21s^iv	3.35 (6)	C9···K^i	4.429 (8)
C1···H21s^iv	3.354 (7)	C6···C14^iii	4.439 (9)
C1···O2s^iv	3.357 (8)	C12···S	4.479 (7)
C6···C15	3.361 (9)	C1···S^iv	4.516 (7)
C14···H81^xi	3.36 (4)	C6···S	4.522 (6)
C16···H82^v	3.36 (7)	O3···K	4.756 (5)
O1···O1s^ii	3.365 (6)	O1···K^i	4.845 (4)
C3···C10	3.366 (9)	K···H12s^ii	4.896 (1)
C3···H22s^iv	3.367 (5)	K···H101^xiv	4.91 (5)
O1···H22s	3.367 (4)	C3···K	4.935 (6)
C7···C14	3.368 (9)	K···H92^xiv	4.97 (7)
C12···H161	3.37 (4)	K···H4^xiii	4.99 (5)
C6···H92^ix	3.37 (6)	C3···K^i	5.068 (6)
O1···H12s^ii	3.370 (4)	K···H91^ix	5.09 (6)
C5···H162	3.37 (6)	K···H21s^iv	5.136 (2)
C4···C11	3.375 (9)	C11···K^i	5.176 (7)
C4···C13	3.379 (9)	K···H101^i	5.18 (5)
H4···H21s	3.38 (5)	C2···K^i	5.210 (6)
C11···H7^ii	3.38 (5)	C9···K^iv	5.249 (8)
C13···H161^xi	3.38 (5)	K···H12s^ix	5.269 (2)
C13···H6	3.39 (5)	K···H92^ix	5.27 (7)
C7···H15	3.39 (5)	K···O2s^x	5.313 (5)
C12···H82^vii	3.39 (6)	C2···K^iv	5.360 (6)
H14···H162	3.39 (8)	C10···K^i	5.361 (7)
C1···H11s^iv	3.393 (6)	O3···K^iv	5.362 (5)
O3···H12s^i	3.393 (5)	S···K^iv	5.414 (2)
C9···H7	3.41 (5)	K···O1s^ii	5.450 (5)
C1···C15	3.416 (9)	O2···K^xiv	5.465 (5)
O2···H11s^i	3.419 (4)	C3···K^xiii	5.480 (6)
C1···H11	3.42 (5)	K···O1s^ix	5.539 (4)
C5···H12	3.42 (6)	C4···K	5.601 (6)
K···H22s^xiii	3.421 (1)	C4···K^xiii	5.649 (6)
C15···H82^vii	3.42 (8)	C2···K	5.653 (6)
C12···H161^xi	3.43 (4)	K···K^ix	5.753 (2)
C11···O3	3.426 (8)	K···K^iv	5.753 (2)
C6···H12^xii	3.43 (6)	K···K^i	5.851 (2)
C2···H11	3.43 (5)	K···K^xiv	5.851 (2)
H12···H161^xi	3.43 (8)
H101—C1—H102	104 (5)	C11—C10—C9	119.7 (6)
H101—C1—C2	112 (3)	H11—C11—C12	119 (3)
H101—C1—C9	111 (3)	H11—C11—C10	120 (3)
H102—C1—C2	115 (3)	C12—C11—C10	120.5 (6)
H102—C1—C9	101 (3)	H12—C12—C11	120 (4)
C2—C1—C9	112.7 (5)	H12—C12—C13	119 (4)
C7—C2—C3	115.8 (5)	C11—C12—C13	120.9 (6)
C7—C2—C1	118.3 (5)	C14—C13—C12	116.8 (6)
C3—C2—C1	124.8 (5)	C14—C13—C16	120.9 (6)
C2—C3—C4	121.0 (5)	C12—C13—C16	120.8 (6)
C2—C3—S	121.5 (4)	H14—C14—C15	123 (3)
C4—C3—S	117.4 (4)	H14—C14—C13	116 (3)
H4—C4—C3	119 (3)	C15—C14—C13	121.0 (6)
H4—C4—C5	120 (3)	H15—C15—C14	117 (3)
C3—C4—C5	120.4 (5)	H15—C15—C10	122 (3)
C6—C5—C4	116.7 (5)	C14—C15—C10	120.9 (6)
C6—C5—C8	120.8 (6)	H162—C16—H161	97 (5)
C4—C5—C8	121.6 (6)	H162—C16—C13	112 (3)
H6—C6—C7	122 (3)	H162—C16—C8	114 (4)
H6—C6—C5	117 (3)	H161—C16—C13	114 (3)
C7—C6—C5	120.3 (6)	H161—C16—C8	106 (3)
H7—C7—C6	121 (3)	C13—C16—C8	112.5 (6)
H7—C7—C2	118 (3)	S—O2—K	120.6 (2)
C6—C7—C2	121.8 (6)	O3—S—O1	112.4 (3)
H82—C8—H81	104 (5)	O3—S—O2	112.8 (3)
H82—C8—C5	113 (4)	O3—S—C3	108.7 (3)
H82—C8—C16	110 (4)	O1—S—O2	111.7 (3)
H81—C8—C5	112 (3)	O1—S—C3	106.2 (3)
H81—C8—C16	104 (3)	O2—S—C3	104.6 (3)
C5—C8—C16	113.4 (6)	O1s—K—O2s	106.9 (1)
H91—C9—H92	104 (6)	O1s—K—O2	80.3 (1)
H91—C9—C10	109 (4)	O2s—K—O2	89.9 (1)
H91—C9—C1	107 (4)	H12s—O1s—H11s	98.0 (4)
H92—C9—C10	113 (4)	H12s—O1s—K	112.9 (3)
H92—C9—C1	109 (4)	H11s—O1s—K	144.7 (3)
C10—C9—C1	114.1 (6)	H21s—O2s—H22s	92.9 (4)
C15—C10—C11	116.6 (6)	H21s—O2s—K	108.0 (3)
C15—C10—C9	122.5 (6)	H22s—O2s—K	145.2 (3)
C9—C1—C2—C3	−88.1 (7)	H81—C8—C16—H161	−8 (5)
C9—C1—C2—C7	79.4 (7)	H81—C8—C16—H162	97 (5)
H101—C1—C2—C3	146 (4)	H82—C8—C16—C13	116 (4)
H101—C1—C2—C7	−47 (4)	H82—C8—C16—H161	−119 (6)
H102—C1—C2—C3	27 (4)	H82—C8—C16—H162	−13 (6)
H102—C1—C2—C7	−166 (3)	C1—C9—C10—C11	80.6 (8)
C2—C1—C9—C10	−2.8 (8)	C1—C9—C10—C15	−86.6 (8)
C2—C1—C9—H91	118 (5)	H91—C9—C10—C11	−39 (5)
C2—C1—C9—H92	−130 (4)	H91—C9—C10—C15	153 (5)
H101—C1—C9—C10	124 (4)	H92—C9—C10—C11	−154 (4)
H101—C1—C9—H91	−115 (6)	H92—C9—C10—C15	38 (4)
H101—C1—C9—H92	−3 (6)	C9—C10—C11—C12	−153.7 (7)
H102—C1—C9—C10	−126 (3)	C9—C10—C11—H11	16 (4)
H102—C1—C9—H91	−5 (6)	C15—C10—C11—C12	14.3 (9)
H102—C1—C9—H92	107 (5)	C15—C10—C11—H11	−176 (4)
C1—C2—C3—C4	149.7 (6)	C9—C10—C15—C14	153.5 (7)
C1—C2—C3—S	−26.8 (8)	C9—C10—C15—H15	−26 (4)
C7—C2—C3—C4	−18.1 (8)	C11—C10—C15—C14	−14 (1)
C7—C2—C3—S	165.4 (5)	C11—C10—C15—H15	166 (4)
C1—C2—C7—C6	−152.7 (6)	C10—C11—C12—C13	0 (1)
C1—C2—C7—H7	26 (4)	C10—C11—C12—H12	175 (4)
C3—C2—C7—C6	15.9 (9)	H11—C11—C12—C13	−170 (3)
C3—C2—C7—H7	−166 (3)	H11—C11—C12—H12	4 (5)
C2—C3—C4—C5	3.5 (9)	C11—C12—C13—C14	−15 (1)
C2—C3—C4—H4	−169 (3)	C11—C12—C13—C16	151.8 (7)
S—C3—C4—C5	−179.9 (5)	H12—C12—C13—C14	171 (4)
S—C3—C4—H4	8 (3)	H12—C12—C13—C16	−23 (4)
C2—C3—S—O1	−170.0 (5)	C12—C13—C14—C15	15 (1)
C2—C3—S—O2	−51.8 (5)	C12—C13—C14—H14	−172 (3)
C2—C3—S—O3	68.9 (5)	C16—C13—C14—C15	−151.6 (7)
C4—C3—S—O1	13.4 (5)	C16—C13—C14—H14	21 (3)
C4—C3—S—O2	131.6 (5)	C12—C13—C16—C8	−69.6 (9)
C4—C3—S—O3	−107.7 (5)	C12—C13—C16—H161	170 (3)
C3—C4—C5—C6	13.7 (9)	C12—C13—C16—H162	61 (4)
C3—C4—C5—C8	−154.9 (6)	C14—C13—C16—C8	96.2 (8)
H4—C4—C5—C6	−174 (3)	C14—C13—C16—H161	−25 (3)
H4—C4—C5—C8	17 (3)	C14—C13—C16—H162	−133 (4)
C4—C5—C6—C7	−16.1 (9)	C13—C14—C15—C10	0 (1)
C4—C5—C6—H6	172 (3)	C13—C14—C15—H15	179 (4)
C8—C5—C6—C7	152.7 (6)	H14—C14—C15—C10	−173 (3)
C8—C5—C6—H6	−20 (3)	H14—C14—C15—H15	7 (5)
C4—C5—C8—C16	98.3 (7)	K—O2—S—C3	−122.0 (3)
C4—C5—C8—H81	−144 (3)	K—O2—S—O1	−7.6 (3)
C4—C5—C8—H82	−28 (4)	K—O2—S—O3	120.1 (3)
C6—C5—C8—C16	−70.0 (8)	S—O2—K—O1s	127.3 (3)
C6—C5—C8—H81	47 (3)	S—O2—K—O2s	20.2 (3)
C6—C5—C8—H82	164 (4)	O2—K—O1s—H11s	−39.0 (5)
C5—C6—C7—C2	1 (1)	O2—K—O1s—H12s	109.9 (3)
C5—C6—C7—H7	−177 (4)	O2s—K—O1s—H11s	47.9 (6)
H6—C6—C7—C2	173 (3)	O2s—K—O1s—H12s	−163.2 (3)
H6—C6—C7—H7	−5 (5)	O2—K—O2s—H21s	−11.8 (3)
C5—C8—C16—C13	−11.9 (9)	O2—K—O2s—H22s	112.2 (6)
C5—C8—C16—H161	114 (3)	O1s—K—O2s—H21s	−91.7 (3)
C5—C8—C16—H162	−141 (4)	O1s—K—O2s—H22s	32.3 (6)
H81—C8—C16—C13	−134 (3)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1; (ii) x, y+1, z; (iii) −x+1/2, y−1/2, −z+2; (iv) x−1/2, −y+3/2, z; (v) −x+1, −y+2, −z+2; (vi) x+1/2, −y+5/2, z; (vii) x−1/2, −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, y−1, z; (xiii) −x+1, −y+2, −z+1; (xiv) −x+1/2, y−1/2, −z+1.

(PCF2) [2.2]paracyclophane-4,15-disulfonic anhydride

Crystal data

C16H14S2O5.1/2CH2Cl2	F(000) = 1496
Mr = 392.9	Dx = 1.641 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 23 reflections
a = 15.927 (2) Å	θ = 40.0–44.9°
b = 7.7031 (4) Å	µ = 4.80 mm^−1
c = 26.257 (2) Å	T = 211 K
β = 98.17 (1)°	Plate, colourless
V = 3188.7 (5) Å^3	0.88 × 0.25 × 0.06 mm
Z = 8

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 59.9°, θmin = 3.4°
Graphite monochromator	h = −17→17
θ/2θ scans	k = 0→8
2357 measured reflections	l = 0→29
2357 independent reflections	2 standard reflections every 60 min
2176 reflections with refl observed if I > 2.5 σ(I )	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	Riding
R[F^2 > 2σ(F^2)] = 0.061	1/[7.6 + 0.0038*σ(Fobs)^2 + 0.00002/σ(Fobs)]
wR(F^2) = 0.067	(Δ/σ)max = 0.337
S = 0.98	Δρmax = 0.88 e Å^−3
2125 reflections	Δρmin = −0.55 e Å^−3
283 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
15 restraints	Extinction coefficient: 1435 (92)

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3727 (4)	0.4668 (8)	0.3312 (2)	0.034 (3)
C2	0.3458 (3)	0.4004 (7)	0.3811 (2)	0.029 (3)
C3	0.4010 (3)	0.3482 (7)	0.4235 (2)	0.028 (3)
C4	0.3774 (4)	0.2244 (8)	0.4589 (2)	0.031 (3)
C5	0.2953 (3)	0.1569 (8)	0.4507 (2)	0.032 (3)
C6	0.2358 (4)	0.2393 (8)	0.4160 (2)	0.034 (3)
C7	0.2605 (4)	0.3608 (8)	0.3814 (2)	0.033 (3)
C8	0.2778 (4)	−0.0220 (9)	0.4720 (2)	0.040 (3)
C9	0.3935 (4)	0.3110 (8)	0.2941 (2)	0.034 (3)
C10	0.3781 (3)	0.1324 (8)	0.3162 (2)	0.030 (3)
C11	0.4344 (3)	0.0524 (7)	0.3539 (2)	0.028 (3)
C12	0.4076 (4)	−0.0680 (7)	0.3883 (2)	0.031 (3)
C13	0.3218 (3)	−0.1084 (7)	0.3844 (2)	0.030 (3)
C14	0.2700 (4)	−0.0605 (8)	0.3406 (2)	0.035 (3)
C15	0.2978 (4)	0.0597 (8)	0.3065 (2)	0.034 (3)
C16	0.2860 (4)	−0.1735 (9)	0.4317 (2)	0.040 (3)
S1	0.50861 (8)	0.4039 (2)	0.43174 (5)	0.0325 (8)
S2	0.54240 (8)	0.1101 (2)	0.36609 (6)	0.0333 (8)
O1	0.5209 (3)	0.5850 (5)	0.4222 (2)	0.047 (2)
O2	0.5539 (2)	0.3242 (6)	0.4752 (2)	0.045 (2)
O3	0.5400 (2)	0.3177 (5)	0.3798 (1)	0.031 (2)
O4	0.5835 (2)	0.0225 (6)	0.4094 (2)	0.044 (2)
O5	0.5791 (3)	0.1144 (6)	0.3194 (2)	0.048 (3)
C1s	0.50000	−0.205 (2)	0.25000	0.090 (9)
Cl1s	0.5686 (1)	−0.3281 (2)	0.29318 (7)	0.058 (1)
H101	0.426 (2)	0.533 (7)	0.343 (2)	0.04 (2)*
H102	0.323 (2)	0.525 (6)	0.310 (2)	0.03 (1)*
H4	0.423 (2)	0.192 (7)	0.488 (1)	0.02 (1)*
H6	0.175 (1)	0.207 (7)	0.408 (2)	0.02 (1)*
H7	0.216 (2)	0.395 (6)	0.352 (1)	0.02 (1)*
H81	0.320 (2)	−0.045 (6)	0.503 (1)	0.02 (1)*
H82	0.215 (1)	−0.03 (1)	0.472 (3)	0.07 (2)*
H91	0.4561 (9)	0.316 (8)	0.294 (2)	0.04 (2)*
H92	0.353 (2)	0.320 (6)	0.261 (1)	0.01 (1)*
H12	0.451 (2)	−0.103 (6)	0.418 (1)	0.01 (1)*
H14	0.208 (1)	−0.088 (8)	0.332 (2)	0.04 (2)*
H15	0.252 (2)	0.097 (7)	0.278 (1)	0.03 (2)*
H161	0.327 (3)	−0.251 (6)	0.453 (2)	0.04 (2)*
H162	0.229 (2)	−0.223 (7)	0.419 (2)	0.04 (2)*
H1s	0.515 (6)	−0.319 (4)	0.236 (3)	0.08 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (3)	0.033 (3)	0.035 (3)	0.004 (3)	0.005 (3)	0.003 (3)
C2	0.028 (3)	0.023 (3)	0.036 (3)	0.005 (2)	0.008 (2)	−0.006 (3)
C3	0.025 (3)	0.026 (3)	0.033 (3)	0.000 (2)	0.009 (2)	−0.010 (2)
C4	0.032 (3)	0.034 (3)	0.028 (3)	0.004 (3)	0.006 (2)	−0.005 (3)
C5	0.030 (3)	0.040 (4)	0.029 (3)	0.000 (3)	0.012 (2)	−0.006 (3)
C6	0.025 (3)	0.039 (4)	0.039 (3)	0.001 (3)	0.011 (3)	−0.008 (3)
C7	0.027 (3)	0.034 (3)	0.038 (3)	0.007 (3)	0.003 (2)	−0.006 (3)
C8	0.042 (4)	0.042 (4)	0.039 (4)	−0.008 (3)	0.012 (3)	0.007 (3)
C9	0.037 (3)	0.038 (4)	0.029 (3)	0.003 (3)	0.008 (3)	0.004 (3)
C10	0.032 (3)	0.035 (3)	0.024 (3)	0.001 (3)	0.008 (2)	−0.009 (3)
C11	0.024 (3)	0.029 (3)	0.030 (3)	0.002 (2)	0.005 (2)	−0.010 (3)
C12	0.031 (3)	0.025 (3)	0.036 (3)	0.004 (3)	0.000 (2)	−0.006 (3)
C13	0.031 (3)	0.022 (3)	0.038 (3)	−0.000 (2)	0.003 (3)	−0.007 (3)
C14	0.026 (3)	0.036 (4)	0.043 (4)	−0.003 (3)	0.002 (3)	−0.010 (3)
C15	0.031 (3)	0.041 (4)	0.030 (3)	0.003 (3)	−0.000 (2)	−0.007 (3)
C16	0.041 (4)	0.036 (4)	0.044 (4)	−0.007 (3)	0.007 (3)	0.007 (3)
S1	0.0247 (7)	0.0372 (9)	0.0356 (8)	−0.0025 (6)	0.0049 (6)	−0.0080 (7)
S2	0.0237 (7)	0.0352 (8)	0.0420 (8)	0.0040 (6)	0.0080 (6)	−0.0066 (7)
O1	0.048 (3)	0.029 (2)	0.066 (3)	−0.011 (2)	0.019 (2)	−0.008 (2)
O2	0.026 (2)	0.066 (3)	0.040 (2)	0.003 (2)	−0.003 (2)	−0.009 (2)
O3	0.031 (2)	0.026 (2)	0.038 (2)	−0.002 (2)	0.014 (2)	−0.009 (2)
O4	0.025 (2)	0.050 (3)	0.056 (3)	0.013 (2)	−0.003 (2)	−0.001 (2)
O5	0.043 (2)	0.055 (3)	0.051 (3)	0.003 (2)	0.026 (2)	−0.012 (2)
C1s	0.14 (1)	0.032 (6)	0.079 (9)	0.00000	−0.049 (9)	0.00000
Cl1s	0.051 (1)	0.054 (1)	0.064 (1)	0.0013 (9)	−0.0106 (8)	0.0029 (9)

Geometric parameters (Å, º)

C1—H102	1.00 (4)	C10—C11	1.383 (7)
C1—H101	1.00 (4)	C10—C15	1.386 (8)
C1—C2	1.523 (9)	C11—C12	1.403 (8)
C1—C9	1.610 (9)	C11—S2	1.761 (5)
C2—C3	1.377 (7)	C12—H12	1.00 (3)
C2—C7	1.394 (8)	C12—C13	1.392 (8)
C3—C4	1.418 (8)	C13—C14	1.368 (8)
C3—S1	1.750 (5)	C13—C16	1.523 (9)
C4—H4	1.00 (3)	C14—H14	1.00 (2)
C4—C5	1.396 (8)	C14—C15	1.403 (9)
C5—C6	1.372 (8)	C15—H15	1.00 (4)
C5—C8	1.528 (9)	C16—H161	1.00 (5)
C6—H6	1.00 (2)	C16—H162	1.00 (3)
C6—C7	1.398 (9)	S1—O2	1.402 (4)
C7—H7	1.00 (3)	S1—O1	1.436 (5)
C8—H82	1.00 (2)	S1—O3	1.657 (4)
C8—H81	1.00 (3)	S2—O4	1.403 (4)
C8—C16	1.594 (9)	S2—O5	1.431 (5)
C9—H91	1.00 (2)	S2—O3	1.640 (4)
C9—H92	1.00 (3)	C1s—H1s	1.00 (5)
C9—C10	1.526 (9)	C1s—Cl1s	1.741 (7)
Cl1s···H1s	1.61 (8)	H92···H1s^iv	3.48 (7)
H161···H162	1.70 (6)	H6···H81^xiii	3.48 (7)
H101···H102	1.74 (5)	C8···H162^vi	3.48 (5)
H91···H92	1.74 (4)	H7···H92	3.49 (5)
H81···H82	1.76 (4)	C13···H6	3.49 (4)
C16···H82	1.99 (6)	C11···S1	3.495 (6)
C2···H101	2.01 (5)	C12···H81	3.50 (3)
C15···H14	2.01 (4)	C1s···H101^x	3.51 (5)
C7···H6	2.02 (4)	C1s···H101^xiv	3.51 (5)
C14···H15	2.02 (4)	C10···H7	3.51 (4)
C10···H91	2.02 (5)	O5···H162^v	3.51 (4)
C8···H161	2.03 (5)	H101···H1s^iii	3.5 (1)
C10···H92	2.04 (4)	O1···H161^iii	3.52 (5)
C11···H12	2.04 (4)	C5···H82^xiii	3.53 (8)
C13···H162	2.04 (4)	H101···H7	3.54 (5)
C6···H7	2.05 (4)	O1···O4^iii	3.544 (6)
C5···H82	2.05 (6)	H102···H15	3.54 (7)
C3···H4	2.06 (4)	O2···O2^ix	3.552 (7)
C9···H102	2.07 (5)	C8···O4^ii	3.552 (7)
H82···H162	2.07 (9)	C9···H15^i	3.55 (4)
C2···H102	2.08 (4)	Cl1s···H91^xiv	3.56 (6)
C5···H81	2.08 (4)	H91···H92^viii	3.56 (5)
H81···H161	2.09 (7)	C9···H91^viii	3.56 (5)
C2···H7	2.09 (3)	C6···H162	3.56 (6)
C13···H161	2.09 (5)	C9···H14^i	3.57 (5)
C1···H91	2.11 (5)	C3···H12	3.57 (5)
C13···H14	2.11 (3)	H102···H14^iii	3.59 (7)
C5···H6	2.11 (3)	C1···H15	3.60 (5)
C10···H15	2.12 (4)	Cl1s···H102^xiv	3.60 (4)
C13···H12	2.12 (3)	C7···H161^iii	3.61 (5)
C16···H81	2.13 (4)	C15···H102	3.61 (5)
H102···H92	2.13 (6)	H161···H162^vi	3.61 (8)
C1···H92	2.14 (3)	C4···O3	3.614 (7)
C5···H4	2.14 (3)	C4···O1^ix	3.619 (7)
C8···H162	2.15 (5)	O3···H82^v	3.62 (5)
C9···H101	2.16 (5)	O3···Cl1s^iii	3.622 (4)
H14···H15	2.19 (7)	H91···H15	3.63 (5)
H101···H91	2.21 (8)	C14···H7	3.63 (5)
H6···H7	2.24 (6)	O1···Cl1s^iii	3.637 (5)
C11···C15	2.349 (7)	C3···H91	3.64 (6)
O4···H12	2.35 (4)	S1···H6^v	3.64 (4)
C3···C7	2.353 (7)	C11···C1s	3.643 (9)
C12···C14	2.366 (8)	C6···O1^xv	3.648 (7)
O3···O5	2.374 (6)	S1···H91	3.66 (6)
H102···H7	2.37 (6)	C2···H162^iii	3.66 (5)
C4···C6	2.376 (8)	C3···O2^ix	3.663 (7)
O1···O3	2.380 (6)	C12···O3	3.668 (7)
O2···H4	2.39 (4)	C8···O2^ii	3.670 (8)
C13···C15	2.406 (8)	C7···O5^xii	3.671 (7)
C5···C7	2.407 (8)	C7···H92	3.67 (3)
C11···C13	2.409 (8)	C14···H82	3.69 (7)
O1···H101	2.42 (5)	C6···H82^xiii	3.69 (7)
C3···C5	2.420 (8)	C5···C11	3.690 (8)
C10···C14	2.428 (8)	C6···C8^xiii	3.691 (9)
C2···C6	2.429 (8)	C1···C13^iii	3.693 (8)
H92···H15	2.43 (6)	C5···C6^xiii	3.693 (8)
C10···C12	2.437 (8)	C8···C16^vi	3.70 (1)
C2···C4	2.443 (8)	O3···H6^v	3.70 (4)
O3···H91	2.45 (5)	S1···H162^v	3.70 (3)
O1···O2	2.458 (6)	C11···H4	3.70 (4)
O4···O5	2.459 (6)	C9···Cl1s^iv	3.707 (7)
O3···O4	2.470 (6)	C8···H14	3.71 (5)
H14···H162	2.48 (8)	C11···H101	3.71 (5)
O2···O3	2.483 (6)	C2···H15	3.71 (4)
H6···H82	2.49 (9)	C2···C16^iii	3.715 (9)
C1···C7	2.503 (9)	C15···H6	3.72 (4)
C9···C15	2.513 (9)	C15···Cl1s^xii	3.720 (6)
O5···H91	2.52 (4)	C10···O5^viii	3.721 (7)
C12···C16	2.518 (9)	S2···H14^v	3.72 (4)
H4···H81	2.52 (6)	C11···H14	3.72 (2)
C14···C16	2.525 (9)	O3···H12	3.72 (4)
C6···C8	2.526 (9)	C5···H14	3.73 (5)
C4···C8	2.528 (9)	C14···Cl1s^xii	3.730 (6)
H102···H15^i	2.53 (6)	C4···H6^xiii	3.73 (5)
O2···H161^ii	2.54 (5)	C16···H4	3.73 (4)
C15···H92	2.54 (4)	O3···H4	3.73 (4)
O3···H101	2.55 (4)	C7···H81^xiii	3.73 (4)
H12···H161	2.56 (6)	C3···H6	3.74 (2)
C9···C11	2.563 (8)	C7···H14	3.74 (6)
C1···C3	2.569 (8)	O4···H4	3.74 (4)
C7···H102	2.57 (5)	C2···C12	3.738 (8)
C14···H162	2.57 (5)	C7···C13	3.742 (8)
H82···H161	2.58 (8)	C12···H15	3.75 (4)
O4···H81^ii	2.58 (3)	C15···H12	3.75 (3)
C8···C13	2.585 (9)	C8···H82^vi	3.75 (8)
C6···H82	2.59 (8)	C5···C8^xiii	3.749 (9)
C5···C16	2.594 (9)	C4···H161	3.75 (5)
C2···C9	2.601 (8)	C13···H4	3.75 (4)
C4···H81	2.60 (5)	Cl1s···H101^xiv	3.75 (6)
C1···C10	2.609 (9)	S2···H101	3.75 (5)
C11···O4	2.613 (6)	C7···H4	3.76 (4)
H92···H14^i	2.62 (6)	C12···O5	3.756 (8)
C3···O2	2.620 (6)	C4···H7	3.76 (3)
C3···H101	2.62 (6)	C1···Cl1s^iii	3.757 (7)
C11···H91	2.62 (6)	C1···C6	3.762 (9)
C11···O5	2.637 (7)	C11···C16	3.763 (9)
O1···H12^iii	2.64 (4)	C6···C12	3.766 (8)
C3···O3	2.645 (7)	C8···O2^xv	3.771 (8)
C3···O1	2.645 (7)	C9···C14	3.772 (9)
H101···H1s^iv	2.7 (1)	C7···C8	3.774 (9)
C12···H161	2.66 (5)	C15···C16	3.775 (9)
C11···O3	2.672 (6)	C8···H81^vi	3.78 (5)
S2···H12	2.68 (4)	C3···C8	3.783 (9)
C12···S2	2.681 (6)	C3···H82^xiii	3.79 (7)
C1···H7	2.68 (4)	C6···C10	3.790 (8)
C4···S1	2.685 (6)	C16···H161^vi	3.79 (5)
O1···H6^v	2.69 (3)	C7···C11	3.795 (8)
S1···H101	2.69 (5)	C5···H81^xiii	3.80 (5)
S1···H4	2.69 (4)	C2···C13^iii	3.805 (8)
S2···H91	2.69 (5)	C10···C1s	3.81 (1)
C11···C14	2.734 (8)	C4···O1	3.807 (7)
H102···H91	2.74 (6)	C5···H6^xiii	3.81 (5)
C2···S1	2.741 (5)	C9···C12	3.812 (8)
C3···C6	2.742 (8)	C4···C10	3.814 (8)
C12···C15	2.753 (8)	C6···H15	3.82 (4)
H82···H161^vi	2.75 (9)	C7···C16^iii	3.824 (9)
C5···C13	2.756 (8)	C3···C13	3.828 (8)
C10···S2	2.760 (5)	C1···C4	3.828 (8)
C4···C7	2.763 (8)	S2···H6^vii	3.83 (4)
C16···H12	2.77 (4)	S2···H81^ii	3.83 (3)
C9···H15	2.77 (4)	S1···H4^ix	3.83 (5)
C2···C10	2.772 (8)	C7···Cl1s^xii	3.849 (6)
C8···H6	2.79 (4)	C2···C14	3.851 (8)
O5···H7^vii	2.80 (4)	O2···H4^ix	3.86 (5)
C16···H14	2.80 (5)	C6···H4^xiii	3.86 (4)
C10···C13	2.814 (8)	C1···Cl1s^iv	3.861 (7)
C2···C5	2.814 (8)	O5···H1s^viii	3.87 (5)
O2···H82^v	2.82 (4)	C5···C15	3.866 (8)
H101···H92	2.82 (6)	C1···S2	3.871 (6)
C8···H4	2.82 (4)	C11···H1s^viii	3.87 (6)
H92···H15^i	2.82 (6)	C9···H1s^iii	3.87 (7)
H81···H162	2.83 (6)	S2···C1s	3.879 (8)
O4···H6^vii	2.84 (5)	C9···S1	3.880 (6)
C12···O4	2.862 (7)	C12···H102^x	3.88 (5)
H91···H91^viii	2.87 (7)	O2···H12	3.88 (4)
C4···O2	2.886 (7)	O5···H12	3.88 (4)
H81···H162^vi	2.90 (7)	C2···O2	3.886 (6)
Cl1s···Cl1s^viii	2.916 (2)	C10···O4	3.890 (6)
O4···H7^vii	2.94 (4)	S1···H161^ii	3.89 (5)
S1···S2	2.940 (2)	C1···C12^iii	3.894 (8)
O2···H81^ii	2.94 (4)	C3···O4	3.896 (7)
O1···H4^ix	2.96 (4)	C2···S2	3.913 (6)
H91···H1s^iv	2.97 (8)	S1···H12^iii	3.91 (5)
O2···O4	2.972 (6)	C6···Cl1s^xii	3.914 (6)
O5···H92^viii	2.97 (4)	O1···H4	3.91 (5)
Cl1s···H101^x	2.98 (5)	C14···O5^xv	3.917 (7)
C4···C12	2.998 (8)	C4···O4^ii	3.918 (7)
H4···H12	3.00 (6)	S1···S1^ix	3.924 (2)
C9···O3	3.004 (6)	C14···H92	3.93 (4)
C1···O3	3.014 (7)	C4···S2	3.928 (6)
C3···C11	3.015 (8)	S1···O1^ix	3.932 (5)
O4···H162^v	3.02 (4)	S2···Cl1s	3.932 (2)
H4···H12^ii	3.04 (5)	C7···S2^xii	3.939 (6)
C4···H12	3.05 (4)	C2···C13	3.940 (8)
O3···H162^v	3.05 (3)	C9···Cl1s^iii	3.940 (7)
Cl1s···H14^vii	3.06 (4)	C6···H102	3.95 (5)
Cl1s···H15^vii	3.06 (4)	C5···C10	3.946 (8)
O5···H14^v	3.07 (5)	C15···H162	3.95 (5)
H7···H15	3.10 (6)	C8···H6^xiii	3.96 (5)
C13···H82	3.11 (6)	C3···C15	3.956 (8)
C5···C12	3.118 (8)	C8···C8^vi	3.96 (1)
H6···H14	3.12 (8)	C1s···H91^xiv	3.96 (6)
Cl1s···H7^vii	3.14 (4)	C1s···H91^x	3.96 (6)
C6···C14	3.139 (9)	C16···O3^xv	3.960 (7)
C2···H91	3.14 (5)	C16···O4^xv	3.961 (8)
C10···H102	3.14 (5)	O1···H91	3.96 (6)
C1···H1s^iv	3.15 (8)	C1···H1s^iii	3.96 (8)
C7···C15	3.152 (9)	C13···O1^x	3.966 (7)
C2···C11	3.158 (8)	C7···H82	3.97 (8)
C13···H81	3.16 (3)	C4···O2^ix	3.969 (7)
C2···O3	3.164 (7)	O5···H15^viii	3.97 (4)
C6···C13	3.171 (8)	S2···O1	3.976 (5)
O1···O2^ix	3.176 (6)	C4···C6^xiii	3.978 (9)
C2···O1	3.180 (7)	S1···O5	3.984 (5)
O4···H4^ii	3.18 (4)	C4···C14	3.985 (8)
H81···H161^vi	3.18 (6)	C5···S1	3.986 (6)
C5···H162	3.18 (5)	C13···S2	3.987 (6)
C5···H161	3.19 (5)	C4···C5^xiii	3.988 (8)
C10···O5	3.193 (7)	O3···H92	3.99 (3)
C15···H7	3.20 (4)	O5···H102^vii	3.99 (4)
O3···H14^v	3.20 (4)	C14···H101^x	3.99 (5)
C10···O3	3.202 (6)	C4···C8^xiii	3.993 (9)
C1···S1	3.204 (6)	S2···H4	3.99 (4)
O5···C1s	3.21 (1)	C3···H81	3.99 (4)
C9···S2	3.212 (6)	C7···S1	3.999 (6)
C2···H92	3.22 (3)	C16···H7^x	4.00 (4)
C14···H92^xi	3.22 (3)	O3···H102	4.00 (4)
H102···H1s^iv	3.23 (9)	C12···H91	4.00 (6)
C7···C10	3.232 (8)	C1s···H102^x	4.01 (4)
C10···H101	3.23 (5)	C1s···H102^xiv	4.01 (4)
C7···H101	3.23 (4)	C15···S2	4.005 (6)
C14···H6	3.24 (5)	C1···H161^iii	4.01 (5)
C1···O1	3.241 (7)	C4···O4	4.010 (7)
C8···C12	3.244 (9)	C11···H101^x	4.01 (5)
C3···C10	3.247 (8)	C1···C14^iii	4.013 (9)
C6···O4^xii	3.250 (7)	C10···S1	4.013 (5)
S1···O4	3.255 (5)	S1···H12	4.01 (5)
C13···H15	3.26 (4)	S1···H161^iii	4.02 (5)
C15···H91	3.26 (4)	C4···H101	4.02 (6)
C7···O4^xii	3.261 (7)	C16···O2^xv	4.021 (8)
Cl1s···H6^vii	3.26 (4)	C6···C11	4.024 (8)
C10···H14	3.27 (4)	C7···H82^xiii	4.03 (7)
C4···C13	3.269 (8)	C12···H82	4.03 (5)
C12···H4	3.27 (4)	C1···C1s^iii	4.04 (1)
C5···H7	3.27 (4)	C12···H4^ii	4.04 (3)
C8···H161^vi	3.27 (5)	C7···C12	4.039 (8)
C3···H7	3.27 (3)	C16···H162^vi	4.04 (5)
Cl1s···H91^x	3.27 (5)	C11···O2	4.052 (7)
C12···O1^x	3.276 (7)	C14···O3^xv	4.054 (7)
C2···H6	3.28 (3)	O4···Cl1s	4.057 (5)
S2···O2	3.288 (5)	C12···O2^ii	4.061 (7)
C11···H15	3.29 (4)	C12···S1	4.072 (6)
C6···C16	3.290 (9)	C11···Cl1s	4.083 (6)
C12···H162	3.29 (4)	S1···H81^ii	4.08 (4)
C10···H12	3.29 (4)	C16···C16^vi	4.09 (1)
S2···H7^vii	3.29 (4)	C15···O5^viii	4.097 (8)
C14···H12	3.30 (3)	C3···O1^ix	4.099 (7)
C4···C11	3.298 (8)	S2···H92	4.11 (3)
C4···H82	3.30 (5)	O5···O5^viii	4.126 (6)
C2···C15	3.300 (8)	S1···H102	4.13 (4)
C14···H161	3.30 (5)	C3···C16^iii	4.134 (9)
O2···H12^ii	3.30 (4)	C5···O4^ii	4.137 (7)
O1···H82^v	3.30 (3)	Cl1s···H102^x	4.15 (4)
C9···O5	3.305 (7)	C11···O1^x	4.168 (7)
C11···H92	3.31 (4)	C7···C8^xiii	4.171 (9)
C12···H14	3.31 (2)	C1···C16^iii	4.193 (9)
C2···H4	3.31 (4)	C8···O1^xv	4.196 (8)
H81···H12	3.31 (5)	C9···C15^i	4.200 (8)
C6···H4	3.31 (3)	C9···C14^i	4.201 (8)
C2···H161^iii	3.31 (5)	C7···C13^iii	4.202 (8)
C6···H81	3.31 (4)	C3···C14	4.209 (8)
C4···H6	3.32 (2)	C2···C12^iii	4.210 (8)
C5···C14	3.316 (8)	C4···C15	4.218 (8)
C12···H101^x	3.32 (5)	C16···O1^x	4.219 (8)
C6···H14	3.33 (6)	C9···O1	4.236 (7)
O5···H91^viii	3.34 (6)	C12···C1s	4.240 (7)
C15···H92^xi	3.34 (4)	C13···O4	4.248 (7)
C3···H102	3.34 (4)	C15···C1s	4.251 (8)
C3···C12	3.342 (8)	C9···C13	4.259 (8)
C9···H1s^iv	3.34 (6)	C1···C5	4.261 (9)
C8···H12	3.34 (4)	C1···C15^i	4.262 (8)
S1···H82^v	3.35 (2)	C10···C16	4.263 (9)
S2···H162^v	3.35 (3)	C2···C8	4.264 (9)
O2···H162^v	3.35 (4)	C13···O2^ii	4.266 (7)
C7···C9	3.356 (9)	S2···H92^viii	4.27 (3)
C16···H81^vi	3.37 (4)	C6···S2^xii	4.269 (6)
C1···C11	3.368 (8)	C12···O2	4.272 (7)
C7···H15	3.37 (4)	C4···S1^ix	4.274 (6)
C6···H81^xiii	3.37 (4)	C5···O2	4.276 (7)
C1···C15	3.385 (9)	S2···H1s^viii	4.28 (5)
H91···H1s^iii	3.39 (8)	C8···C11	4.285 (9)
Cl1s···H92^xiv	3.39 (4)	C8···S1^xv	4.306 (7)
C15···H102^xi	3.39 (4)	C1···O5	4.309 (8)
C3···C9	3.395 (8)	C3···S1^ix	4.314 (5)
C5···H12	3.40 (4)	C12···Cl1s	4.318 (6)
H81···H82^vi	3.40 (9)	C7···C16	4.324 (9)
H101···H12^iii	3.41 (7)	C9···C1s^iii	4.32 (1)
C16···H82^vi	3.41 (8)	S2···O1^x	4.335 (5)
C1···H15^i	3.41 (4)	C16···S2^xv	4.346 (6)
H4···H6^xiii	3.41 (6)	O5···Cl1s^iii	4.349 (5)
C7···H162^iii	3.41 (5)	C5···O1^xv	4.362 (7)
C3···S2	3.416 (6)	C9···C9^viii	4.372 (9)
H7···H162^iii	3.42 (7)	C8···O3^xv	4.373 (7)
H6···H162	3.42 (7)	C6···C9	4.374 (9)
C3···H161^iii	3.42 (5)	C6···C6^xiii	4.375 (8)
C4···C16	3.425 (9)	C6···O5^xii	4.383 (7)
C9···O5^viii	3.426 (8)	C1···C12	4.392 (8)
C14···H102^x	3.43 (5)	C1···C14	4.398 (9)
C7···C14	3.428 (9)	S1···Cl1s^iii	4.404 (2)
C4···H82^xiii	3.43 (7)	C5···O4^xii	4.410 (7)
C13···H102^x	3.43 (5)	C2···C14^iii	4.412 (8)
C16···H6	3.43 (5)	C4···C9	4.420 (8)
H82···H162^vi	3.45 (9)	C3···C8^xiii	4.434 (9)
C8···C14	3.449 (9)	C3···C16	4.435 (9)
C5···C5^xiii	3.451 (8)	C16···S1^xv	4.458 (7)
C9···H7	3.45 (4)	C12···S1^x	4.462 (6)
C6···C15	3.459 (9)	C6···S1	4.488 (6)
S1···O2^ix	3.470 (5)	C14···S2	4.491 (6)
C13···H101^x	3.47 (5)	C6···S1^xv	4.513 (6)
C16···O2^ii	3.473 (7)	C14···S2^xv	4.552 (6)
O5···Cl1s	3.477 (5)	S2···Cl1s^iii	4.774 (2)
H102—C1—H101	121 (4)	C11—C10—C9	123.5 (5)
H102—C1—C2	109 (3)	C15—C10—C9	119.2 (5)
H102—C1—C9	102 (3)	C10—C11—C12	122.1 (5)
H101—C1—C2	103 (3)	C10—C11—S2	122.3 (4)
H101—C1—C9	109 (3)	C12—C11—S2	115.4 (4)
C2—C1—C9	112.2 (5)	H12—C12—C13	125 (2)
C3—C2—C7	116.3 (5)	H12—C12—C11	116 (2)
C3—C2—C1	124.6 (5)	C13—C12—C11	119.1 (5)
C7—C2—C1	118.1 (5)	C14—C13—C12	118.0 (5)
C2—C3—C4	121.8 (5)	C14—C13—C16	121.6 (5)
C2—C3—S1	122.0 (4)	C12—C13—C16	119.4 (5)
C4—C3—S1	115.5 (4)	H14—C14—C13	126 (3)
H4—C4—C5	126 (3)	H14—C14—C15	113 (3)
H4—C4—C3	116 (3)	C13—C14—C15	120.6 (5)
C5—C4—C3	118.6 (5)	H15—C15—C10	125 (3)
C6—C5—C4	118.2 (5)	H15—C15—C14	114 (3)
C6—C5—C8	121.1 (5)	C10—C15—C14	121.1 (5)
C4—C5—C8	119.6 (5)	H161—C16—H162	117 (4)
H6—C6—C5	125 (3)	H161—C16—C13	111 (3)
H6—C6—C7	113 (3)	H161—C16—C8	101 (3)
C5—C6—C7	120.6 (5)	H162—C16—C13	106 (3)
H7—C7—C2	121 (2)	H162—C16—C8	110 (3)
H7—C7—C6	116 (2)	C13—C16—C8	112.1 (5)
C2—C7—C6	120.9 (5)	O2—S1—O1	120.1 (3)
H82—C8—H81	123 (5)	O2—S1—O3	108.3 (2)
H82—C8—C5	107 (5)	O2—S1—C3	112.0 (3)
H82—C8—C16	98 (4)	O1—S1—O3	100.4 (2)
H81—C8—C5	109 (3)	O1—S1—C3	111.9 (3)
H81—C8—C16	108 (3)	O3—S1—C3	101.8 (2)
C5—C8—C16	112.4 (5)	O4—S2—O5	120.4 (3)
H91—C9—H92	121 (4)	O4—S2—O3	108.3 (2)
H91—C9—C10	105 (4)	O4—S2—C11	110.9 (3)
H91—C9—C1	105 (4)	O5—S2—O3	101.0 (2)
H92—C9—C10	106 (3)	O5—S2—C11	111.0 (3)
H92—C9—C1	108 (3)	O3—S2—C11	103.5 (2)
C10—C9—C1	112.6 (5)	S2—O3—S1	126.2 (3)
C11—C10—C15	116.0 (5)	H1s—C1s—Cl1s	66 (4)
C9—C1—C2—C3	82.0 (7)	H81—C8—C16—C13	−111 (3)
C9—C1—C2—C7	−86.2 (6)	H81—C8—C16—H161	6 (4)
H101—C1—C2—C3	−36 (3)	H81—C8—C16—H162	130 (4)
H101—C1—C2—C7	156 (3)	H82—C8—C16—C13	120 (4)
H102—C1—C2—C3	−165 (3)	H82—C8—C16—H161	−122 (5)
H102—C1—C2—C7	26 (3)	H82—C8—C16—H162	2 (6)
C2—C1—C9—C10	2.3 (6)	C1—C9—C10—C11	−79.1 (7)
C2—C1—C9—H91	−111 (4)	C1—C9—C10—C15	87.3 (6)
C2—C1—C9—H92	118 (2)	H91—C9—C10—C11	35 (4)
H101—C1—C9—C10	116 (3)	H91—C9—C10—C15	−159 (4)
H101—C1—C9—H91	3 (5)	H92—C9—C10—C11	164 (2)
H101—C1—C9—H92	−128 (4)	H92—C9—C10—C15	−30 (2)
H102—C1—C9—C10	−114 (3)	C9—C10—C11—C12	152.6 (6)
H102—C1—C9—H91	132 (4)	C9—C10—C11—S2	−21.0 (8)
H102—C1—C9—H92	1 (4)	C15—C10—C11—C12	−14.1 (8)
C1—C2—C3—C4	−152.8 (6)	C15—C10—C11—S2	172.2 (4)
C1—C2—C3—S1	17.1 (8)	C9—C10—C15—C14	−153.3 (6)
C7—C2—C3—C4	15.7 (8)	C9—C10—C15—H15	18 (3)
C7—C2—C3—S1	−174.4 (4)	C11—C10—C15—C14	14.1 (9)
C1—C2—C7—C6	154.0 (6)	C11—C10—C15—H15	−175 (3)
C1—C2—C7—H7	−11 (3)	C10—C11—C12—C13	−0.0 (9)
C3—C2—C7—C6	−15.3 (9)	C10—C11—C12—H12	−170 (3)
C3—C2—C7—H7	180 (3)	S2—C11—C12—C13	174.0 (4)
C2—C3—C4—C5	−1.3 (9)	S2—C11—C12—H12	4 (3)
C2—C3—C4—H4	178 (3)	C10—C11—S2—O3	58.1 (5)
S1—C3—C4—C5	−171.8 (5)	C10—C11—S2—O4	174.0 (5)
S1—C3—C4—H4	7 (3)	C10—C11—S2—O5	−49.5 (6)
C2—C3—S1—O1	47.1 (6)	C12—C11—S2—O3	−116.0 (4)
C2—C3—S1—O2	−174.8 (5)	C12—C11—S2—O4	−0.1 (5)
C2—C3—S1—O3	−59.3 (5)	C12—C11—S2—O5	136.5 (4)
C4—C3—S1—O1	−142.3 (4)	C11—C12—C13—C14	14.7 (8)
C4—C3—S1—O2	−4.2 (5)	C11—C12—C13—C16	−154.5 (5)
C4—C3—S1—O3	111.2 (4)	H12—C12—C13—C14	−176 (3)
C3—C4—C5—C6	−14.0 (9)	H12—C12—C13—C16	15 (3)
C3—C4—C5—C8	154.5 (6)	C12—C13—C14—C15	−14.8 (9)
H4—C4—C5—C6	167 (3)	C12—C13—C14—H14	176 (4)
H4—C4—C5—C8	−25 (3)	C16—C13—C14—C15	154.1 (6)
C4—C5—C6—C7	14.5 (9)	C16—C13—C14—H14	−15 (4)
C4—C5—C6—H6	−176 (4)	C12—C13—C16—C8	73.8 (7)
C8—C5—C6—C7	−153.8 (6)	C12—C13—C16—H161	−38 (3)
C8—C5—C6—H6	15 (4)	C12—C13—C16—H162	−166 (3)
C4—C5—C8—C16	−91.7 (6)	C14—C13—C16—C8	−95.0 (7)
C4—C5—C8—H81	28 (2)	C14—C13—C16—H161	154 (3)
C4—C5—C8—H82	162 (4)	C14—C13—C16—H162	26 (3)
C6—C5—C8—C16	76.4 (7)	C13—C14—C15—C10	0.2 (9)
C6—C5—C8—H81	−164 (2)	C13—C14—C15—H15	−172 (3)
C6—C5—C8—H82	−29 (5)	H14—C14—C15—C10	170 (4)
C5—C6—C7—C2	0.4 (9)	H14—C14—C15—H15	−2 (5)
C5—C6—C7—H7	166 (3)	C3—S1—O3—S2	−64.9 (3)
H6—C6—C7—C2	−170 (3)	O1—S1—O3—S2	179.9 (3)
H6—C6—C7—H7	−4 (4)	O2—S1—O3—S2	53.2 (3)
C5—C8—C16—C13	8.4 (7)	C11—S2—O3—S1	68.4 (3)
C5—C8—C16—H161	126 (3)	O4—S2—O3—S1	−49.3 (3)
C5—C8—C16—H162	−110 (3)	O5—S2—O3—S1	−176.7 (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, −y−1/2, −z+1; (vii) x+1/2, y−1/2, z; (viii) −x+1, y, −z+1/2; (ix) −x+1, −y+1, −z+1; (x) x, y−1, z; (xi) −x+1/2, y−1/2, −z+1/2; (xii) x−1/2, y+1/2, z; (xiii) −x+1/2, −y+1/2, −z+1; (xiv) −x+1, y−1, −z+1/2; (xv) x−1/2, y−1/2, z.

(PCF3) [2.2]paracyclophane-4,15-disulfonimide

Crystal data

C16H15NS2O4.2CH3CN	F(000) = 452
Mr = 431.54	Dx = 1.46 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2y1	Cell parameters from 23 reflections
a = 8.725 (7) Å	θ = 19.0–20.9°
b = 10.259 (7) Å	µ = 0.31 mm^−1
c = 10.950 (6) Å	T = 293 K
β = 92.87 (4)°	Rod, colourless
V = 979 (1) Å^3	1.00 × 0.35 × 0.25 mm
Z = 2

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 29.9°, θmin = 1.9°
Graphite monochromator	h = −12→12
θ/2θ scans	k = −14→0
2982 measured reflections	l = 0→15
2982 independent reflections	2 standard reflections every 60 min
2011 reflections with refl observed if I > 2.5 σ(I )	intensity decay: 10%

Refinement

Refinement on F	12 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.056	Riding
wR(F^2) = 0.064	1/[8.3 + 0.0072*σ(Fobs)^2 + 0.00006/σ(Fobs)]
S = 0.76	(Δ/σ)max = 0.307
2011 reflections	Δρmax = 0.55 e Å^−3
175 parameters	Δρmin = −0.58 e Å^−3

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4839 (5)	0.6714 (4)	0.9760 (3)	0.035 (2)
C2	0.3939 (4)	0.6152 (3)	0.8666 (3)	0.029 (2)
C3	0.4507 (4)	0.6032 (3)	0.7490 (3)	0.027 (1)
C4	0.3532 (4)	0.6042 (4)	0.6441 (3)	0.032 (2)
C5	0.1949 (4)	0.6157 (4)	0.6545 (4)	0.036 (2)
C6	0.1383 (4)	0.5972 (4)	0.7699 (4)	0.040 (2)
C7	0.2362 (4)	0.5960 (4)	0.8737 (4)	0.036 (2)
C8	0.0957 (5)	0.6715 (4)	0.5493 (4)	0.048 (2)
S1	0.6499 (1)	0.60528 (9)	0.72663 (8)	0.0304 (4)
O1	0.6727 (3)	0.5972 (3)	0.5988 (2)	0.042 (1)
O2	0.7298 (3)	0.5183 (3)	0.8104 (3)	0.044 (2)
N	0.7121 (5)	0.75000	0.7766 (4)	0.030 (2)
C1s	−0.0669 (9)	0.25000	0.7999 (7)	0.054 (4)
C2s	0.0351 (7)	0.25000	0.9069 (6)	0.044 (3)
C4s	0.4696 (9)	0.25000	0.6627 (6)	0.051 (4)
N1s	0.1164 (7)	0.25000	0.9907 (5)	0.066 (4)
C3s	0.309 (1)	0.25000	0.6771 (9)	0.069 (5)
N2s	0.5986 (9)	0.25000	0.6494 (7)	0.076 (5)
H11	0.592 (2)	0.638 (5)	0.977 (5)	0.08000*
H12	0.431 (5)	0.646 (5)	1.052 (3)	0.08000*
H4	0.399 (5)	0.611 (6)	0.562 (2)	0.08000*
H6	0.024 (1)	0.602 (6)	0.771 (5)	0.08000*
H7	0.195 (5)	0.599 (6)	0.957 (2)	0.08000*
H81	−0.015 (2)	0.649 (5)	0.560 (4)	0.08000*
H82	0.139 (5)	0.649 (5)	0.469 (2)	0.08000*
H1n	0.770 (8)	0.75000	0.858 (3)	0.08000*
H11s	−0.011 (8)	0.25000	0.723 (4)	0.08000*
H12s	−0.131 (5)	0.329 (3)	0.782 (5)	0.08000*
H31s	0.274 (9)	0.25000	0.763 (3)	0.08000*
H32s	0.252 (5)	0.328 (3)	0.645 (5)	0.08000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.047 (2)	0.030 (2)	0.028 (2)	0.001 (2)	0.001 (2)	0.004 (1)
C2	0.037 (2)	0.016 (1)	0.034 (2)	0.001 (1)	0.001 (1)	0.003 (1)
C3	0.030 (1)	0.016 (1)	0.035 (2)	−0.000 (1)	0.001 (1)	0.000 (1)
C4	0.039 (2)	0.021 (1)	0.037 (2)	−0.003 (1)	−0.002 (1)	−0.005 (2)
C5	0.037 (2)	0.022 (2)	0.049 (2)	−0.006 (1)	−0.008 (2)	−0.006 (2)
C6	0.032 (2)	0.026 (2)	0.063 (2)	−0.005 (2)	0.004 (2)	−0.003 (2)
C7	0.041 (2)	0.023 (2)	0.045 (2)	−0.002 (2)	0.009 (2)	0.003 (2)
C8	0.043 (2)	0.043 (2)	0.055 (3)	−0.004 (2)	−0.017 (2)	−0.003 (2)
S1	0.0309 (4)	0.0235 (4)	0.0369 (4)	0.0030 (4)	0.0023 (3)	−0.0022 (4)
O1	0.048 (2)	0.038 (1)	0.042 (1)	−0.002 (1)	0.011 (1)	−0.010 (1)
O2	0.042 (2)	0.030 (1)	0.060 (2)	0.010 (1)	−0.005 (1)	0.005 (1)
N	0.028 (2)	0.024 (2)	0.037 (2)	0.00000	−0.005 (2)	0.00000
C1s	0.055 (4)	0.049 (4)	0.055 (4)	0.00000	−0.023 (3)	0.00000
C2s	0.042 (3)	0.041 (3)	0.050 (4)	0.00000	−0.001 (3)	0.00000
C4s	0.063 (4)	0.040 (3)	0.048 (4)	0.00000	0.001 (3)	0.00000
N1s	0.063 (4)	0.082 (5)	0.050 (3)	0.00000	−0.016 (3)	0.00000
C3s	0.070 (5)	0.044 (4)	0.094 (7)	0.00000	0.027 (5)	0.00000
N2s	0.075 (5)	0.074 (5)	0.079 (5)	0.00000	−0.013 (4)	0.00000

Geometric parameters (Å, º)

C1—H12	1.00 (4)	C8—H81	1.00 (2)
C1—H11	1.00 (3)	C8—C8^i	1.610 (7)
C1—C2	1.513 (5)	S1—O1	1.426 (3)
C1—C1^i	1.613 (5)	S1—O2	1.435 (3)
C2—C7	1.396 (5)	S1—N	1.664 (2)
C2—C3	1.409 (5)	N—H1n	1.00 (4)
C3—C4	1.395 (5)	C1s—H12s^ii	0.99 (4)
C3—S1	1.767 (4)	C1s—H12s	0.99 (4)
C4—H4	1.00 (3)	C1s—H11s	1.00 (5)
C4—C5	1.396 (5)	C1s—C2s	1.44 (1)
C5—C6	1.393 (6)	C2s—N1s	1.131 (9)
C5—C8	1.519 (6)	C4s—N2s	1.14 (1)
C6—H6	1.00 (1)	C4s—C3s	1.42 (1)
C6—C7	1.387 (6)	C3s—H32s^ii	1.00 (4)
C7—H7	1.00 (3)	C3s—H32s	1.00 (4)
C8—H82	1.00 (3)	C3s—H31s	1.00 (4)
H11s···H12s^ii	1.50 (7)	C8···H4^i	3.46 (5)
H11s···H12s	1.50 (7)	S1···H12s^iv	3.46 (4)
H31s···H32s^ii	1.52 (5)	N2s···H11s^iv	3.46 (7)
H31s···H32s	1.52 (5)	H4···H82^i	3.46 (7)
H32s···H32s^ii	1.60 (5)	N2s···H12^vi	3.47 (3)
H12s···H12s^ii	1.61 (5)	N2s···H12^iii	3.47 (3)
H11···H12	1.67 (5)	C3···S1^i	3.474 (4)
H81···H82	1.72 (5)	C3···H32s	3.47 (4)
N1s···H1n^iii	1.89 (5)	C3···H12^vi	3.49 (5)
C5···H6	2.02 (3)	H11···H7	3.49 (5)
C2s···H11s	2.04 (4)	C5···H4^i	3.50 (5)
C2···H7	2.05 (4)	H81···H32s^v	3.50 (6)
C2···H12	2.06 (3)	O1···H6^iv	3.52 (3)
C4s···H32s^ii	2.06 (4)	C5···H6^i	3.53 (5)
C4s···H32s	2.06 (4)	H6···H82	3.54 (6)
H82···H82^i	2.06 (8)	C1···C2^vi	3.546 (5)
C3···H4	2.07 (3)	S1···H81^iv	3.55 (3)
C2···H11	2.07 (3)	C2s···C3s	3.56 (1)
C4s···H31s	2.08 (7)	C8···H81^ix	3.56 (5)
H81···H81^i	2.08 (8)	C1···H31s^xii	3.56 (5)
C5···H81	2.08 (3)	C1···C1^vi	3.565 (6)
C8···H82^i	2.08 (5)	C2···H1n	3.57 (6)
C6···H7	2.08 (2)	C2···H7^i	3.57 (5)
C8···H81^i	2.09 (5)	C1···N1s^xii	3.580 (8)
C5···H4	2.09 (4)	H82···H32s^ix	3.58 (6)
C5···H82	2.10 (3)	C4···N2s^xvii	3.588 (8)
C2s···H12s^ii	2.10 (4)	C3···H4^i	3.59 (5)
C2s···H12s	2.10 (4)	N···H81^iv	3.60 (4)
C1···H12^i	2.11 (5)	N···H81^xv	3.60 (4)
C7···H6	2.12 (3)	C2s···H32s	3.60 (5)
H12···H12^i	2.13 (8)	C2s···H32s^ii	3.60 (5)
C1···H11^i	2.17 (5)	C1s···C3s	3.60 (1)
S1···H1n	2.28 (4)	C8···N2s^xvii	3.616 (9)
H11···H11^i	2.29 (7)	C8···H32s^ix	3.62 (5)
H12···H7	2.31 (6)	C2s···H11^vi	3.62 (3)
O2···H12s^iv	2.32 (4)	C2s···H11^iii	3.62 (3)
H6···H81	2.36 (7)	H4···H81	3.63 (5)
H11···H1n	2.37 (7)	C6···H12s	3.63 (4)
C3···C7	2.373 (5)	C1···O2^vi	3.630 (5)
C4···C6	2.383 (6)	C4···H82^i	3.63 (5)
O1···H4	2.41 (5)	S1···H12^vi	3.64 (4)
O2···N	2.409 (3)	H12s···H31s	3.64 (9)
C3···C5	2.416 (5)	C7···O2^vi	3.651 (5)
C5···C7	2.417 (6)	C7···H12^i	3.65 (5)
C2···C6	2.428 (5)	O1···H32s^xvii	3.65 (4)
C2···C4	2.447 (5)	C8···H12s^ix	3.66 (5)
O2···H1n	2.45 (1)	O1···N2s	3.668 (4)
H6···H7	2.46 (5)	N1s···H7	3.67 (6)
H4···H82	2.47 (6)	N1s···H7^ii	3.67 (6)
O1···O2	2.481 (4)	C4···C3s	3.674 (5)
H11s···H31s	2.5 (1)	C6···H81^i	3.68 (5)
C1···C7	2.507 (6)	C4···N	3.700 (6)
O1···N	2.509 (5)	C6···O2^xi	3.703 (5)
C4···C8	2.524 (6)	C3s···H81^xvi	3.71 (4)
C6···C8	2.544 (6)	C3s···H81^ix	3.71 (4)
H82···H11s^v	2.54 (6)	C1s···H6^ii	3.72 (6)
O2···H11	2.55 (5)	C1s···H6	3.72 (6)
C3s···N2s	2.56 (1)	O2···H11s^iv	3.72 (4)
C1s···N1s	2.57 (1)	C7···H32s	3.72 (4)
C7···H12	2.57 (4)	O2···H82^vii	3.74 (4)
C1···C3	2.584 (5)	C6···H1n^xi	3.74 (6)
C5···C8^i	2.597 (6)	C6···H7^i	3.74 (5)
C1···C2^i	2.598 (5)	C3···H6	3.75 (1)
C3···O1	2.604 (4)	C3···C4s	3.750 (4)
H11s···H32s^ii	2.61 (8)	C4s···H12s^iv	3.75 (4)
H11s···H32s	2.61 (8)	C4s···H12s^x	3.75 (4)
C1···H7	2.63 (5)	C7···H6^i	3.75 (5)
C8···H6	2.64 (5)	C1···C6	3.753 (6)
C3···O2	2.641 (5)	C6···H31s	3.75 (2)
C6···H81	2.65 (4)	C4···H7	3.76 (3)
C4···H82	2.65 (4)	C5···O1^vii	3.759 (5)
C2s···H31s	2.68 (7)	C3···C5^i	3.760 (5)
H81···H82^i	2.69 (7)	C7···H4	3.76 (3)
C4···S1	2.699 (4)	S1···N2s	3.763 (3)
O2···H12^vi	2.70 (4)	C3···C8	3.768 (6)
C8···H4	2.71 (5)	O1···H12s^iv	3.77 (4)
N2s···H4^vii	2.72 (4)	C7···H31s	3.77 (1)
N2s···H4^viii	2.72 (4)	C4···C4s	3.776 (5)
N···H11	2.73 (5)	C2···C4^i	3.777 (5)
N···H11^i	2.73 (5)	O2···H12s^x	3.78 (3)
C3···N	2.737 (5)	C7···C8	3.780 (6)
C3···C6	2.748 (5)	C4···O2	3.780 (5)
C3···H11	2.75 (5)	C1s···H12^xiii	3.79 (4)
H82···H12s^ix	2.75 (6)	C1s···H12^xiv	3.79 (4)
C5···C5^i	2.755 (5)	N···H4^i	3.79 (4)
O2···H6^iv	2.76 (2)	N···H4	3.79 (4)
C4···C7	2.762 (5)	C7···C2s^xviii	3.799 (7)
C2···C2^i	2.765 (5)	C3s···H12^iii	3.80 (4)
S1···H4	2.77 (4)	C3s···H12^vi	3.80 (4)
H11···H12^i	2.77 (7)	C3···H11^i	3.81 (5)
C2···S1	2.774 (4)	O1···H81^xv	3.81 (4)
N1s···H11^iii	2.79 (3)	C5···C7^i	3.814 (6)
N1s···H11^vi	2.79 (3)	C2···C6^i	3.816 (5)
O1···H4^vii	2.82 (5)	C1···C4	3.817 (5)
N2s···H12s^iv	2.83 (4)	C6···H11s	3.82 (2)
N2s···H12s^x	2.83 (4)	C7···N1s^xviii	3.824 (7)
C2···C5	2.829 (5)	C8···O1^vii	3.827 (6)
O1···H81^iv	2.83 (2)	C8···O1^xi	3.833 (6)
S1···H11	2.83 (5)	O1···H4^i	3.84 (5)
H4···H4^i	2.86 (8)	O1···N2s^xvii	3.848 (7)
C4···O1	2.857 (5)	S1···H11^i	3.85 (5)
C3s···H11s	2.86 (7)	C6···N1s^xviii	3.854 (7)
O2···H7^vi	2.87 (3)	O2···H81^iv	3.86 (4)
N2s···H82^viii	2.87 (5)	S1···H4^vii	3.87 (4)
N2s···H82^vii	2.87 (5)	O2···C4s	3.870 (6)
H6···H1n^xi	2.88 (7)	C5···H81^ix	3.87 (5)
O1···H32s^vii	2.89 (5)	C2s···H7	3.87 (6)
N···N1s^xii	2.890 (7)	C2s···H7^ii	3.87 (6)
N1s···H31s	2.91 (5)	C8···H82^ix	3.88 (5)
H11···H12^vi	2.94 (7)	C7···H12^vi	3.88 (5)
C4···H32s	2.97 (4)	C4···C6^i	3.881 (6)
S1···S1^i	2.970 (2)	C5···C3s	3.886 (5)
C1···H1n	2.98 (6)	C3···C7^i	3.892 (5)
C2s···H7^xiii	2.99 (5)	C4···H4^vii	3.89 (5)
C2s···H7^xiv	2.99 (5)	C2s···H6^xiv	3.89 (5)
H81···H32s^ix	2.99 (6)	C2s···H6^xiii	3.89 (5)
C4···C4^i	2.992 (6)	S1···H82^vii	3.90 (5)
C5···H32s	3.00 (3)	N1s···C3s	3.90 (1)
C3···C3^i	3.013 (5)	C3···C3s	3.897 (5)
C2s···H1n^iii	3.01 (5)	C1···S1^i	3.898 (4)
C1s···H31s	3.02 (8)	C4s···H4	3.90 (6)
H7···H12s^xiii	3.03 (6)	C4s···H4^ii	3.90 (6)
H6···H6^i	3.03 (8)	C8···C1s^v	3.903 (9)
N1s···H11s	3.09 (5)	C8···H32s	3.90 (4)
H7···H7^i	3.09 (8)	C2s···H6^ii	3.91 (6)
C4···H4^i	3.09 (6)	C2s···H6	3.91 (6)
C2···H11^vi	3.11 (5)	C2···O1	3.907 (5)
C4s···H4^vii	3.12 (4)	C4s···H82^vii	3.91 (5)
C4s···H4^viii	3.12 (4)	C4s···H82^viii	3.91 (5)
N···H6^xv	3.12 (3)	S1···N1s^xii	3.913 (6)
N···H6^iv	3.12 (3)	C3···H11^vi	3.92 (5)
H6···H12s	3.12 (6)	C4···H31s	3.93 (2)
O1···H82^vii	3.12 (5)	C7···N1s	3.933 (5)
N2s···H32s	3.13 (5)	C6···H12	3.93 (4)
N2s···H32s^ii	3.13 (5)	O2···C2s^iv	3.938 (6)
H11···H7^vi	3.13 (7)	C3···H31s	3.94 (3)
C1···N	3.133 (6)	C2···C5^i	3.952 (5)
O1···O1^i	3.134 (5)	C8···H32s^v	3.96 (4)
C8···H11s^v	3.14 (4)	C2···H32s	3.97 (4)
C6···C6^i	3.136 (6)	C1···C7^vi	3.975 (6)
N2s···H31s	3.15 (7)	O2···H4	3.98 (4)
C1s···H82^ix	3.15 (3)	C5···H31s	3.98 (2)
C1s···H82^xvi	3.15 (3)	C7···C2s	3.985 (5)
C7···C7^i	3.159 (6)	C6···C2s	3.985 (6)
N1s···H12s	3.17 (5)	C2···S1^i	3.988 (4)
N1s···H12s^ii	3.17 (5)	C1···H7^vi	3.99 (5)
C5···H81^i	3.17 (5)	C2···O2^vi	3.992 (5)
C5···H82^i	3.18 (5)	C8···H12s^v	4.00 (5)
C2···H12^i	3.18 (5)	C3s···H4	4.00 (6)
C2···O2	3.185 (5)	C3s···H4^ii	4.00 (6)
C4···C5^i	3.193 (6)	C7···H12s^xiii	4.00 (5)
C2···H12^vi	3.19 (5)	C6···C1s	4.007 (6)
N1s···H7^xiv	3.20 (5)	C5···S1	4.010 (5)
N1s···H7^xiii	3.20 (5)	C6···C3s	4.010 (6)
C2···C3^i	3.212 (5)	C3s···H11^vi	4.01 (5)
H4···H4^vii	3.23 (7)	C3s···H11^iii	4.01 (5)
C1···S1	3.226 (4)	C7···H81	4.01 (4)
C7···H11^vi	3.23 (5)	C3s···H4^vii	4.01 (4)
H11···H31s^xii	3.24 (6)	C3s···H4^viii	4.01 (4)
C6···H6^i	3.24 (6)	N···C2s^xii	4.014 (8)
C5···C6^i	3.252 (6)	C3···N2s	4.016 (5)
C4···H6	3.26 (3)	S1···H4^i	4.02 (5)
H81···H82^ix	3.26 (7)	S1···C4s	4.018 (4)
C6···H32s	3.26 (4)	C8···C8^ix	4.020 (7)
C2···H11^i	3.26 (5)	C4···S1^i	4.021 (4)
C2···C7^i	3.269 (5)	S1···O2^i	4.022 (4)
C3···H7	3.27 (4)	C3···H82	4.02 (4)
H12···H12s^xiii	3.27 (6)	C7···S1	4.027 (5)
S1···H6^iv	3.27 (1)	C3···O1^i	4.028 (5)
C1···O2	3.278 (5)	C1···C4s^xii	4.039 (8)
C1s···N2s^xi	3.28 (1)	C2···H31s	4.04 (2)
C7···H7^i	3.28 (6)	C6···N^xi	4.040 (6)
O2···C1s^iv	3.280 (5)	C4···C4s^xvii	4.054 (8)
C7···H11	3.28 (3)	O1···C4s	4.055 (5)
H81···H11s^v	3.29 (6)	C5···N2s^xvii	4.101 (8)
C1···H11^vi	3.29 (5)	C3···C6^i	4.123 (6)
C2···N	3.296 (6)	C2···C2^vi	4.124 (5)
C6···H4	3.30 (4)	C4···C7^i	4.133 (6)
N1s···H6^xiv	3.30 (5)	O1···O1^vii	4.135 (4)
N1s···H6^xiii	3.30 (5)	C1···C3^vi	4.142 (5)
H82···H12s^v	3.30 (6)	S1···H12	4.14 (4)
C3···C4^i	3.311 (5)	C4···O1^i	4.188 (5)
H11···H11^vi	3.31 (7)	C1···C3s^xii	4.20 (1)
O1···H1n	3.31 (3)	C7···C3s	4.216 (7)
C5···H7	3.32 (2)	C4···N2s	4.216 (6)
H4···H32s	3.32 (7)	S1···H7^vi	4.22 (4)
C1s···H7^xiii	3.32 (4)	C6···C2s^xviii	4.219 (8)
C1s···H7^xiv	3.32 (4)	C7···C1s^xviii	4.241 (8)
C4···H81	3.32 (2)	C1s···C4s^xi	4.24 (1)
C3···H1n	3.33 (6)	C5···O1	4.248 (6)
C2···H4	3.34 (2)	S1···H32s^vii	4.26 (5)
H81···H81^ix	3.34 (8)	C1···C5	4.264 (6)
C6···H82	3.34 (3)	C6···S1^xi	4.265 (5)
C4···C8^i	3.345 (6)	C2···C8	4.275 (6)
C2···H6	3.35 (2)	C1···N2s^xii	4.278 (8)
C3···H12	3.36 (3)	C8···C3s^v	4.29 (1)
C1···H12^vi	3.36 (5)	C1···O2^i	4.291 (5)
C4···O1^vii	3.367 (5)	C6···N1s	4.314 (6)
S1···O1^i	3.367 (4)	C2···C3s	4.330 (6)
C1···C7^i	3.373 (6)	O2···C2s^xii	4.337 (6)
H12···H31s^xii	3.38 (7)	C8···N^xi	4.345 (7)
C4s···H12^vi	3.38 (3)	C3···C8^i	4.364 (6)
C4s···H12^iii	3.38 (3)	C1···C6^i	4.375 (6)
C6···C8^i	3.394 (6)	C6···O1^xi	4.387 (5)
C1···C3^i	3.396 (5)	C1···C2s^xii	4.401 (8)
O1···C3s^xvii	3.414 (9)	C7···C8^i	4.402 (6)
C1s···H32s	3.42 (5)	C1···C4^i	4.404 (5)
C1s···H32s^ii	3.42 (5)	C5···C8^ix	4.420 (6)
O2···N2s	3.434 (5)	C2···C4s	4.429 (5)
C6···C7^i	3.440 (6)	S1···C1s^iv	4.454 (5)
C8···H6^i	3.44 (5)	C8···S1^xi	4.486 (6)
O1···C4s^xvii	3.441 (7)	C6···S1	4.514 (5)
H12···H12^vi	3.45 (7)	C1···S1^vi	4.517 (4)
C1···H7^i	3.45 (5)	S1···C4s^xvii	4.585 (7)
H6···H81^i	3.45 (7)	C4···S1^vii	4.592 (4)
O2···N1s^xii	3.450 (5)	S1···C3s^xvii	4.69 (1)
H12···H7^i	3.45 (7)
H12—C1—H11	112 (4)	H81—C8—C5	109 (3)
H12—C1—C2	108 (2)	H81—C8—C8^i	104 (3)
H12—C1—C1^i	105 (3)	C5—C8—C8^i	112.1 (3)
H11—C1—C2	109 (3)	O1—S1—O2	120.3 (2)
H11—C1—C1^i	110 (3)	O1—S1—N	108.4 (2)
C2—C1—C1^i	112.4 (3)	O1—S1—C3	108.8 (2)
C7—C2—C3	115.6 (3)	O2—S1—N	101.8 (2)
C7—C2—C1	119.0 (3)	O2—S1—C3	110.7 (2)
C3—C2—C1	124.3 (3)	N—S1—C3	105.8 (2)
C4—C3—C2	121.6 (3)	H1n—N—S1^i	115.7 (5)
C4—C3—S1	116.7 (3)	H1n—N—S1	115.7 (5)
C2—C3—S1	121.3 (2)	S1^i—N—S1	126.4 (3)
H4—C4—C3	119 (2)	H12s^ii—C1s—H12s	109 (3)
H4—C4—C5	120 (2)	H12s^ii—C1s—H11s	97 (4)
C3—C4—C5	119.9 (3)	H12s^ii—C1s—C2s	119 (3)
C6—C5—C4	117.4 (3)	H12s—C1s—H11s	97 (4)
C6—C5—C8	121.7 (3)	H12s—C1s—C2s	119 (3)
C4—C5—C8	119.9 (4)	H11s—C1s—C2s	113 (4)
H6—C6—C7	124 (3)	N1s—C2s—C1s	179.4 (7)
H6—C6—C5	114 (3)	N2s—C4s—C3s	179.0 (8)
C7—C6—C5	120.8 (3)	H32s^ii—C3s—H32s	107 (4)
H7—C7—C6	121 (2)	H32s^ii—C3s—H31s	99 (4)
H7—C7—C2	117 (3)	H32s^ii—C3s—C4s	116 (3)
C6—C7—C2	121.5 (4)	H32s—C3s—H31s	99 (4)
H82—C8—H81	118 (4)	H32s—C3s—C4s	116 (3)
H82—C8—C5	111 (3)	H31s—C3s—C4s	117 (4)
H82—C8—C8^i	103 (3)
H11—C1—C2—C3	−42 (3)	H4—C4—C5—C8	−15 (4)
H11—C1—C2—C7	151 (3)	C4—C5—C6—C7	13.8 (6)
H12—C1—C2—C3	−164 (3)	C4—C5—C6—H6	−177 (4)
H12—C1—C2—C7	28 (3)	C8—C5—C6—C7	−154.6 (4)
C1^i—C1—C2—C3	80.4 (4)	C8—C5—C6—H6	14 (4)
C1^i—C1—C2—C7	−86.9 (4)	C4—C5—C8—H81	163 (3)
C1—C2—C3—C4	−152.6 (3)	C4—C5—C8—H82	32 (3)
C1—C2—C3—S1	19.9 (5)	C4—C5—C8—C8^i	−82.6 (5)
C7—C2—C3—C4	15.1 (5)	C6—C5—C8—H81	−29 (3)
C7—C2—C3—S1	−172.4 (3)	C6—C5—C8—H82	−160 (3)
C1—C2—C7—C6	153.3 (4)	C6—C5—C8—C8^i	85.6 (5)
C1—C2—C7—H7	−15 (4)	C5—C6—C7—C2	0.9 (6)
C3—C2—C7—C6	−15.2 (5)	C5—C6—C7—H7	168 (4)
C3—C2—C7—H7	177 (4)	H6—C6—C7—C2	−167 (4)
C2—C3—C4—C5	−0.8 (5)	H6—C6—C7—H7	0 (6)
C2—C3—C4—H4	170 (4)	C3—S1—N—H1n	104 (4)
S1—C3—C4—C5	−173.6 (3)	C3—S1—N—S1^i	−57.9 (4)
S1—C3—C4—H4	−3 (4)	O1—S1—N—H1n	−139 (4)
C2—C3—S1—O1	−177.4 (3)	O1—S1—N—S1^i	58.6 (4)
C2—C3—S1—O2	48.3 (3)	O2—S1—N—H1n	−11 (4)
C2—C3—S1—N	−61.2 (3)	O2—S1—N—S1^i	−173.7 (3)
C4—C3—S1—O1	−4.6 (3)	H11s—C1s—C2s—N1s	−0.0001 (1)
C4—C3—S1—O2	−138.8 (3)	H12s—C1s—C2s—N1s	−112 (3)
C4—C3—S1—N	111.7 (3)	H12s^ii—C1s—C2s—N1s	112 (3)
C3—C4—C5—C6	−13.8 (5)	N2s—C4s—C3s—H31s	180.0000
C3—C4—C5—C8	154.9 (4)	N2s—C4s—C3s—H32s	−64 (3)
H4—C4—C5—C6	176 (4)	N2s—C4s—C3s—H32s^ii	64 (3)

Symmetry codes: (i) x, −y+3/2, z; (ii) x, −y+1/2, z; (iii) −x+1, y−1/2, −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, y−1/2, −z+1; (ix) −x, −y+1, −z+1; (x) x+1, −y+1/2, z; (xi) x−1, y, z; (xii) −x+1, y+1/2, −z+2; (xiii) −x, −y+1, −z+2; (xiv) −x, y−1/2, −z+2; (xv) x+1, −y+3/2, z; (xvi) −x, y−1/2, −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

Crystal data

C19H21NS2O4	F(000) = 824
Mr = 391.5	Dx = 1.457 Mg m^−3
Orthorhombic, Pmcn	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P -2n 21	Cell parameters from 23 reflections
a = 10.587 (2) Å	θ = 25.0–38.5°
b = 10.779 (3) Å	µ = 2.92 mm^−1
c = 15.644 (5) Å	T = 293 K
V = 1785.3 (8) Å^3	Block, colourless
Z = 4	0.30 × 0.25 × 0.10 mm

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 74.7°, θmin = 5.0°
Graphite monochromator	h = 0→13
θ/2θ scans	k = 0→13
1939 measured reflections	l = −19→0
1939 independent reflections	2 standard reflections every 60 min
804 reflections with refl observed if I > 2.5 σ(I )	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	Riding
R[F^2 > 2σ(F^2)] = 0.089	1/[3.7 + 0.027*σ(Fobs)^2 + 0.0009/σ(Fobs)]
wR(F^2) = 0.095	(Δ/σ)max = 0.021
S = 0.87	Δρmax = 0.59 e Å^−3
804 reflections	Δρmin = −0.49 e Å^−3
125 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
11 restraints	Extinction coefficient: 398 (103)

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3236 (11)	0.4824 (9)	0.9901 (4)	0.040 (7)
C2	0.3806 (12)	0.3594 (10)	0.9641 (7)	0.037 (6)
C3	0.3883 (13)	0.3177 (10)	0.8768 (6)	0.037 (6)
C4	0.3889 (14)	0.1930 (11)	0.8542 (5)	0.045 (7)
C5	0.3804 (13)	0.1023 (11)	0.9182 (8)	0.048 (7)
C6	0.3966 (13)	0.1402 (10)	1.0036 (7)	0.045 (7)
C7	0.3996 (12)	0.2656 (10)	1.0245 (5)	0.039 (7)
C8	0.3210 (12)	−0.0236 (9)	0.8971 (5)	0.061 (9)
C17	0.25000	0.6334 (17)	0.7808 (13)	0.070 (15)
C18	0.25000	0.6477 (17)	0.6800 (14)	0.09 (2)
C19	0.25000	0.7808 (18)	0.6548 (6)	0.14 (3)
N	0.25000	0.4998 (12)	0.8015 (9)	0.031 (7)
S	0.3889 (3)	0.4263 (3)	0.79317 (18)	0.0422 (14)
O1	0.3963 (10)	0.3581 (8)	0.7146 (5)	0.063 (5)
O2	0.4830 (7)	0.5201 (8)	0.8089 (6)	0.052 (5)
H4	0.39433	0.16821	0.79201	0.10000*
H6	0.40693	0.07614	1.05031	0.10000*
H7	0.41594	0.29025	1.08583	0.10000*
H101	0.35483	0.50379	1.04907	0.10000*
H102	0.35483	0.54843	0.94933	0.10000*
H81	0.35231	−0.05062	0.83913	0.10000*
H82	0.35229	−0.08619	0.94059	0.10000*
H171	0.17288	0.67539	0.80498	0.10000*
H181	0.32712	0.60578	0.65610	0.10000*
H191	0.17288	0.82307	0.67834	0.10000*
H192	0.25000	0.78945	0.59100	0.10000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.045 (8)	0.040 (7)	0.036 (6)	−0.013 (6)	0.003 (6)	−0.011 (6)
C2	0.026 (6)	0.038 (7)	0.046 (6)	−0.005 (6)	0.001 (6)	0.003 (5)
C3	0.038 (6)	0.038 (6)	0.034 (5)	−0.001 (7)	0.005 (7)	0.008 (5)
C4	0.047 (7)	0.044 (7)	0.043 (6)	0.000 (8)	−0.001 (7)	−0.004 (6)
C5	0.038 (7)	0.045 (8)	0.063 (7)	0.002 (7)	−0.009 (7)	0.005 (6)
C6	0.036 (7)	0.042 (7)	0.057 (7)	−0.004 (8)	−0.004 (7)	0.010 (6)
C7	0.035 (6)	0.046 (7)	0.036 (6)	−0.002 (7)	−0.013 (6)	0.017 (6)
C8	0.063 (10)	0.030 (6)	0.089 (10)	0.000 (7)	0.019 (9)	−0.007 (8)
C17	0.054 (13)	0.069 (16)	0.087 (18)	0.00000	0.00000	0.006 (16)
C18	0.054 (14)	0.073 (19)	0.15 (3)	0.00000	0.00000	0.059 (19)
C19	0.09 (2)	0.17 (4)	0.16 (3)	0.00000	0.00000	0.08 (3)
N	0.046 (7)	0.018 (7)	0.028 (7)	0.00000	0.00000	0.011 (7)
S	0.0423 (14)	0.0475 (16)	0.0369 (13)	0.0008 (19)	0.0049 (17)	0.0087 (16)
O1	0.084 (7)	0.070 (6)	0.034 (4)	0.016 (6)	0.007 (6)	−0.002 (5)
O2	0.037 (4)	0.052 (5)	0.068 (6)	−0.011 (4)	0.006 (5)	0.016 (5)

Geometric parameters (Å, º)

C1^i—H101^i	1.007 (8)	C8^i—H82^i	1.013 (9)
C1^i—H102^i	1.012 (9)	C8^i—C8^ii	1.504 (18)
C1^i—C2^i	1.512 (15)	C17^i—H171^ii	1.007 (12)
C1^i—C1^ii	1.558 (16)	C17^i—H171^i	1.007 (12)
C2^i—C7^i	1.398 (15)	C17^i—N^i	1.48 (2)
C2^i—C3^i	1.439 (15)	C17^i—C18^i	1.58 (3)
C3^i—C4^i	1.390 (16)	C18^i—H181^ii	1.005 (12)
C3^i—S^i	1.756 (11)	C18^i—H181^i	1.005 (12)
C4^i—H4^i	1.011 (8)	C18^i—C19^i	1.49 (3)
C4^i—C5^i	1.402 (16)	C19^i—H192^i	1.002 (9)
C5^i—C6^i	1.407 (16)	C19^i—H191^ii	1.005 (9)
C5^i—C8^i	1.532 (16)	C19^i—H191^i	1.005 (9)
C6^i—H6^i	1.011 (11)	N^i—S^ii	1.676 (7)
C6^i—C7^i	1.392 (15)	N^i—S^i	1.676 (7)
C7^i—H7^i	1.010 (8)	S^i—O1^i	1.434 (8)
C8^i—H81^i	1.009 (9)	S^i—O2^i	1.441 (9)
H191^i···H192^i	1.6323 (4)	H101^i···H191^iv	3.3590 (5)
H101^i···H102^i	1.6328 (5)	C1^i···C3^ii	3.365 (16)
H171^i···H171^ii	1.6329 (3)	C1^i···C7^ii	3.366 (16)
H181^i···H181^ii	1.6329 (3)	C6^i···H6^ii	3.367 (14)
H191^i···H191^ii	1.6329 (3)	C3^i···H101^i	3.378 (11)
H81^i···H82^i	1.6329 (5)	H82^i···H181	3.3885 (11)
C19^i···H181^i	2.056 (17)	H82^i···H192	3.3926 (7)
C19^i···H181^ii	2.056 (17)	C2^i···H4^i	3.393 (11)
C18^i···H191^ii	2.059 (17)	O1^i···H191^x	3.394 (10)
C18^i···H191^i	2.059 (17)	C17^i···H192^i	3.41 (2)
N^i···H171^i	2.062 (12)	H4^i···H191^x	3.4202 (5)
N^i···H171^ii	2.062 (12)	C3^i···S^ii	3.421 (13)
C2^i···H101^i	2.065 (11)	C6^i···C7^ii	3.430 (18)
C18^i···H192^i	2.07 (2)	H81^i···H191^xv	3.4336 (6)
C8^i···H81^ii	2.068 (12)	H101^i···H101^viii	3.4370 (6)
C2^i···H102^i	2.069 (11)	C4^i···O2^xiii	3.439 (14)
C8^i···H82^ii	2.070 (12)	S^i···H81^vi	3.442 (3)
C6^i···H7^i	2.077 (11)	C1^i···H101^viii	3.463 (11)
C2^i···H7^i	2.079 (11)	C18^i···O2^i	3.471 (17)
C5^i···H81^i	2.083 (12)	C18^i···O2^ii	3.471 (17)
C7^i···H6^i	2.084 (11)	C7^i···H7^ii	3.486 (12)
C5^i···H82^i	2.084 (12)	C8^i···H4^ii	3.490 (11)
C3^i···H4^i	2.089 (11)	C17^i···O1^i	3.50 (2)
C5^i···H4^i	2.103 (12)	C17^i···O1^ii	3.50 (2)
C5^i···H6^i	2.105 (12)	H7^i···H7^ii	3.5136 (7)
C1^i···H101^ii	2.115 (11)	C18^i···O1^i	3.527 (19)
C1^i···H102^ii	2.117 (11)	C18^i···O1^ii	3.527 (19)
C17^i···H181^ii	2.14 (2)	C3^i···H101^viii	3.527 (13)
C17^i···H181^i	2.14 (2)	S^i···H171^i	3.532 (3)
C18^i···H171^i	2.14 (2)	O1^i···H171^x	3.542 (10)
C18^i···H171^ii	2.14 (2)	C1^i···H102^viii	3.549 (11)
H82^i···H82^ii	2.1658 (4)	C8^i···H171^ix	3.551 (10)
H81^i···H81^ii	2.1663 (4)	H81^i···H171^xv	3.5519 (7)
H101^i···H101^ii	2.2196 (4)	C18^i···H6^xvi	3.563 (18)
H102^i···H102^ii	2.2196 (4)	C18^i···H6^v	3.563 (18)
O2^i···H171^ii	2.351 (8)	C1^i···H171^ii	3.567 (8)
H181^i···H191^ii	2.3678 (6)	H7^i···H102^i	3.5669 (7)
H181^i···H192^i	2.3713 (5)	C8^i···H6^ii	3.567 (11)
H6^i···H7^i	2.3758 (6)	H6^i···H181^xvii	3.5671 (5)
O1^i···H4^i	2.378 (8)	C19^i···H81^xviii	3.576 (12)
C3^i···C7^i	2.380 (13)	C19^i···H81^xix	3.576 (12)
C4^i···C6^i	2.407 (13)	C5^i···H4^ii	3.587 (13)
C3^i···C5^i	2.411 (17)	C5^i···H82^iii	3.594 (13)
C5^i···C7^i	2.430 (16)	H4^i···H81^ii	3.5952 (6)
H171^i···H181^ii	2.4470 (7)	C6^i···C8^iii	3.595 (18)
C2^i···C6^i	2.448 (15)	C1^i···H7^ii	3.600 (10)
H7^i···H101^i	2.4591 (6)	H102^i···H102^viii	3.6127 (5)
O1^i···O2^i	2.464 (12)	C1^i···H191^vii	3.615 (8)
N^i···O2^i	2.480 (8)	H6^i···H81^i	3.6216 (10)
N^i···O2^ii	2.480 (8)	H4^i···H82^i	3.6223 (7)
C18^i···N^i	2.48 (2)	C1^i···C2^viii	3.638 (16)
C2^i···C4^i	2.485 (15)	C6^i···H181	3.641 (11)
H4^i···H81^i	2.5110 (6)	C3^i···H4^ii	3.649 (13)
H6^i···H82^i	2.5184 (5)	O1^i···H82^vi	3.652 (9)
C1^i···C7^i	2.528 (15)	C4^i···H81^ii	3.671 (13)
C17^i···C19^i	2.53 (2)	O1^i···H181^ii	3.682 (9)
C4^i···C8^i	2.534 (16)	S^i···H181^ii	3.684 (3)
H171^i···H191^i	2.5414 (6)	O2^i···H171^i	3.686 (8)
C5^i···C8^ii	2.550 (18)	C17^i···H81^xviii	3.688 (18)
C6^i···C8^i	2.555 (14)	C17^i···H81^xix	3.688 (18)
H6^i···H82^iii	2.5554 (5)	C5^i···H6^ii	3.689 (13)
N^i···O1^i	2.565 (14)	C8^i···O1^xiii	3.693 (15)
N^i···O1^ii	2.565 (14)	C7^i···O2^viii	3.697 (13)
C1^i···C2^ii	2.568 (16)	C1^i···C19^iv	3.709 (17)
H101^i···H192^iv	2.5746 (5)	C4^i···N^i	3.712 (17)
C3^i···O1^i	2.577 (12)	S^i···H4^vi	3.720 (3)
O1^i···H7^v	2.580 (8)	C6^i···H82^ii	3.724 (13)
O2^i···H4^vi	2.593 (9)	C5^i···C6^iii	3.729 (18)
C1^i···C3^i	2.600 (14)	C3^i···C5^ii	3.729 (18)
O2^i···H102^i	2.600 (9)	C4^i···O2^i	3.732 (15)
N^i···H102^i	2.619 (12)	C6^i···C6^iii	3.733 (17)
N^i···H102^ii	2.619 (12)	C1^i···C17^i	3.74 (2)
C3^i···O2^i	2.626 (15)	C7^i···H101^ii	3.741 (12)
C7^i···H101^i	2.639 (11)	S^i···H101^viii	3.744 (3)
H102^i···H171^ii	2.6568 (6)	C2^i···H7^ii	3.746 (12)
C4^i···H81^i	2.665 (12)	C6^i···H81^iii	3.749 (13)
O1^i···H6^v	2.668 (7)	C1^i···O2^viii	3.752 (12)
N^i···H181^i	2.672 (13)	C3^i···H102^ii	3.755 (12)
N^i···H181^ii	2.672 (13)	C3^i···C8^i	3.761 (15)
C6^i···H82^i	2.673 (11)	C3^i···H6^i	3.766 (11)
C17^i···S^i	2.681 (16)	C1^i···C1^viii	3.767 (16)
C17^i···S^ii	2.681 (16)	O1^i···H171^ii	3.772 (9)
C4^i···S^i	2.690 (12)	C1^i···C6^i	3.774 (15)
H6^i···H181	2.7015 (5)	C7^i···H101^viii	3.776 (12)
H81^i···H82^ii	2.7126 (4)	C2^i···C4^ii	3.782 (17)
C3^i···N^i	2.718 (16)	C4^i···H7^i	3.783 (8)
C17^i···H191^i	2.723 (19)	C7^i···H4^i	3.786 (8)
C17^i···H191^ii	2.723 (19)	S^i···H102^ii	3.790 (3)
C19^i···H171^i	2.735 (11)	C7^i···C8^i	3.792 (14)
C19^i···H171^ii	2.735 (11)	C18^i···H4^vi	3.797 (3)
C1^i···H7^i	2.736 (9)	C18^i···H4^xx	3.797 (3)
C8^i···H4^i	2.753 (10)	C19^i···N^i	3.80 (2)
H101^i···H102^ii	2.7555 (4)	C8^i···H191^ix	3.802 (8)
C3^i···H102^i	2.756 (11)	S^i···H6^v	3.804 (3)
C3^i···C6^i	2.757 (15)	C3^i···H181^xiii	3.816 (13)
C5^i···C5^ii	2.76 (2)	C2^i···C6^ii	3.818 (18)
C2^i···C2^ii	2.764 (18)	C5^i···C7^ii	3.828 (17)
H101^i···H191^vii	2.7674 (6)	C2^i···H191^x	3.833 (12)
S^i···H171^ii	2.770 (3)	C1^i···C4^i	3.837 (14)
C2^i···S^i	2.771 (11)	C7^i···H6^ii	3.856 (12)
C4^i···C7^i	2.779 (11)	C8^i···O2^xiii	3.862 (13)
C8^i···H6^i	2.779 (9)	C1^i···S^ii	3.863 (9)
S^i···H4^i	2.783 (3)	C4^i···C6^ii	3.863 (18)
C17^i···O2^i	2.788 (12)	C6^i···H181^xiii	3.865 (13)
C17^i···O2^ii	2.788 (12)	C3^i···C7^ii	3.865 (17)
S^i···H102^i	2.798 (3)	C19^i···H102^xi	3.866 (12)
C4^i···O1^i	2.818 (12)	C19^i···H102^xii	3.866 (12)
O2^i···H101^viii	2.819 (9)	C19^i···O2^xx	3.869 (15)
O2^i···H7^viii	2.834 (9)	C19^i···O2^vi	3.869 (15)
C6^i···H82^iii	2.858 (14)	C3^i···H192^x	3.874 (14)
C2^i···C5^i	2.862 (17)	C1^i···H7^viii	3.876 (10)
H81^i···H191^ix	2.8726 (7)	O1^i···O2^xiii	3.878 (13)
H181^i···H191^i	2.8763 (6)	C3^i···C19^x	3.881 (14)
O1^i···H181^i	2.916 (9)	C8^i···H171^xv	3.882 (10)
C3^i···C3^ii	2.93 (2)	O1^i···H4^ii	3.889 (10)
O2^i···H191^x	2.931 (9)	N^i···H4^i	3.890 (12)
C4^i···C4^ii	2.94 (2)	N^i···H4^ii	3.890 (12)
H171^i···H181^i	2.9418 (6)	C4^i···C18^x	3.891 (15)
S^i···S^ii	2.942 (5)	C6^i···H7^ii	3.901 (13)
O1^i···H81^vi	2.959 (10)	C2^i···O1^i	3.906 (13)
S^i···H181^i	2.961 (3)	C1^i···H171^i	3.907 (9)
O2^i···H81^vi	2.997 (9)	C4^i···H171^x	3.909 (12)
C5^i···H6^iii	3.002 (13)	C4^i···H6^iii	3.914 (12)
C17^i···H102^ii	3.00 (2)	O2^i···H4^i	3.917 (9)
C17^i···H102^i	3.00 (2)	C5^i···O2^xiii	3.937 (15)
H6^i···H6^iii	3.0093 (4)	C4^i···C19^x	3.941 (15)
H81^i···H171^ix	3.0131 (8)	C1^i···H191^iv	3.952 (9)
H171^i···H191^ii	3.0208 (5)	C17^i···H4^xx	3.952 (6)
C1^i···H192^iv	3.025 (9)	C17^i···H4^vi	3.952 (6)
H102^i···H192^iv	3.0327 (6)	C18^i···H82^xvi	3.95 (2)
H7^i···H102^viii	3.0358 (5)	C18^i···H82^v	3.95 (2)
C8^i···H6^iii	3.048 (12)	C3^i···O1^ii	3.964 (16)
O2^i···H181^i	3.048 (9)	C2^i···S^ii	3.976 (12)
H4^i···H4^ii	3.0561 (6)	C2^i···C5^ii	3.978 (18)
C1^i···N^i	3.058 (15)	C4^i···S^ii	3.986 (14)
C19^i···H101^xi	3.059 (15)	C7^i···H171^xiv	3.987 (11)
C19^i···H101^xii	3.059 (15)	C3^i···C17^i	4.00 (2)
H6^i···H81^iii	3.0927 (5)	O2^i···H101^i	3.999 (9)
O1^i···O1^ii	3.098 (15)	C1^i···C7^viii	4.003 (16)
C6^i···C6^ii	3.10 (2)	C5^i···S^i	4.004 (13)
H101^i···H102^viii	3.1251 (6)	S^i···H7^v	4.007 (3)
H4^i···H181^xiii	3.1319 (5)	C6^i···H101^i	4.008 (11)
C3^i···H191^x	3.134 (14)	C8^i···H7^iii	4.011 (12)
C4^i···H181^xiii	3.154 (14)	C7^i···S^i	4.014 (9)
C4^i···H4^ii	3.164 (14)	C3^i···H81^i	4.032 (11)
C7^i···C7^ii	3.167 (18)	C2^i···O2^viii	4.048 (14)
C2^i···H101^viii	3.173 (12)	S^i···O2^ii	4.073 (9)
C2^i···O2^i	3.174 (14)	C3^i···C6^ii	4.086 (18)
C4^i···C5^ii	3.18 (2)	S^i···H4^ii	4.091 (3)
C2^i···C3^ii	3.189 (18)	C5^i···O1^xiii	4.103 (16)
C5^i···H81^ii	3.213 (13)	C2^i···C2^viii	4.105 (17)
C5^i···H82^ii	3.213 (13)	S^i···H101^i	4.105 (3)
C1^i···S^i	3.215 (8)	C4^i···C7^ii	4.127 (16)
C2^i···H101^ii	3.225 (12)	C4^i···O1^ii	4.129 (16)
C2^i···H102^ii	3.227 (12)	C7^i···C8^iii	4.130 (16)
H7^i···H171^xiv	3.2334 (5)	S^i···H7^viii	4.145 (3)
S^i···H191^x	3.236 (3)	C8^i···C17^xv	4.19 (2)
C6^i···H6^iii	3.237 (12)	C19^i···S^vi	4.211 (8)
C3^i···C4^ii	3.25 (2)	C19^i···S^xx	4.211 (8)
C5^i···C6^ii	3.25 (2)	C5^i···O1^i	4.216 (15)
C7^i···O1	3.260 (11)	C5^i···C5^iii	4.222 (18)
H4^i···H7^v	3.2644 (10)	C5^i···C18^x	4.232 (16)
C2^i···H102^viii	3.267 (12)	C1^i···C3^viii	4.275 (16)
C2^i···N^i	3.267 (16)	C1^i···C5^i	4.290 (16)
H102^i···H171^i	3.2685 (6)	C2^i···C8^i	4.305 (15)
C2^i···C7^ii	3.273 (17)	C3^i···C8^ii	4.307 (16)
C4^i···C8^ii	3.293 (17)	C8^i···S^xiii	4.311 (11)
C3^i···H7^i	3.296 (10)	C1^i···O2^ii	4.329 (13)
C6^i···O1	3.301 (13)	C3^i···C18^x	4.337 (16)
C7^i···H102^i	3.301 (11)	C2^i···C17^i	4.34 (2)
C5^i···H181^xiii	3.307 (13)	C19^i···O1^vi	4.346 (11)
C7^i···H82^iii	3.308 (12)	C19^i···O1^xx	4.346 (11)
C7^i···H102^viii	3.308 (12)	C5^i···C8^iii	4.365 (17)
C18^i···S^ii	3.316 (18)	C1^i···C6^ii	4.368 (16)
C18^i···S^i	3.316 (18)	C4^i···S^xiii	4.372 (12)
H4^i···H171^x	3.3173 (5)	C7^i···C8^ii	4.376 (15)
H7^i···H82^iii	3.3212 (5)	C1^i···C4^ii	4.394 (15)
C4^i···H82^i	3.322 (11)	C4^i···O1^xiii	4.400 (15)
C4^i···H6^i	3.322 (9)	C8^i···C19^xv	4.403 (15)
H6^i···H6^ii	3.3228 (6)	C2^i···C19^x	4.413 (13)
C6^i···H4^i	3.324 (10)	C4^i···C17^x	4.415 (17)
C1^i···O2^i	3.324 (12)	C6^i···C18	4.43 (2)
C6^i···H81^i	3.327 (11)	C6^i···S^i	4.512 (11)
C5^i···H7^i	3.335 (12)	C5^i···S^xiii	4.527 (13)
S^i···O1^ii	3.342 (11)	C6^i···S	4.587 (11)
H82^i···H171^ix	3.3431 (7)	C19^i···S^i	4.632 (17)
C6^i···C8^ii	3.346 (17)	C19^i···S^ii	4.632 (17)
C2^i···H6^i	3.349 (11)	C1^i···S^viii	4.661 (10)
C4^i···H191^x	3.356 (14)	C7^i···S	4.686 (9)
H101^i—C1^i—H102^i	108.0 (9)	C8^ii—C8^i—C5^i	114.2 (9)
H101^i—C1^i—C2^i	108.5 (9)	H171^ii—C17^i—H171^i	108.4 (18)
H101^i—C1^i—C1^ii	109.2 (8)	H171^ii—C17^i—N^i	110.9 (12)
H102^i—C1^i—C2^i	108.5 (8)	H171^ii—C17^i—C18^i	109.3 (13)
H102^i—C1^i—C1^ii	109.1 (8)	H171^i—C17^i—N^i	110.9 (12)
C2^i—C1^i—C1^ii	113.5 (9)	H171^i—C17^i—C18^i	109.3 (13)
C7^i—C2^i—C3^i	114.0 (10)	N^i—C17^i—C18^i	108.2 (15)
C7^i—C2^i—C1^i	120.6 (9)	H181^ii—C18^i—H181^i	108.6 (19)
C3^i—C2^i—C1^i	123.5 (9)	H181^ii—C18^i—C19^i	109.6 (13)
C4^i—C3^i—C2^i	122.9 (9)	H181^ii—C18^i—C17^i	109.0 (13)
C4^i—C3^i—S^i	117.0 (7)	H181^i—C18^i—C19^i	109.6 (13)
C2^i—C3^i—S^i	119.9 (8)	H181^i—C18^i—C17^i	109.0 (13)
H4^i—C4^i—C3^i	120.1 (10)	C19^i—C18^i—C17^i	110.9 (15)
H4^i—C4^i—C5^i	120.4 (11)	H192^i—C19^i—H191^ii	108.8 (9)
C3^i—C4^i—C5^i	119.5 (9)	H192^i—C19^i—H191^i	108.8 (9)
C4^i—C5^i—C6^i	117.9 (11)	H192^i—C19^i—C18^i	110.7 (16)
C4^i—C5^i—C8^i	119.4 (10)	H191^ii—C19^i—H191^i	108.7 (15)
C6^i—C5^i—C8^i	120.7 (10)	H191^ii—C19^i—C18^i	109.9 (10)
H6^i—C6^i—C7^i	119.4 (9)	H191^i—C19^i—C18^i	109.9 (10)
H6^i—C6^i—C5^i	120.1 (10)	C17^i—N^i—S^ii	116.4 (5)
C7^i—C6^i—C5^i	120.5 (10)	C17^i—N^i—S^i	116.4 (5)
H7^i—C7^i—C6^i	118.8 (9)	S^ii—N^i—S^i	122.8 (8)
H7^i—C7^i—C2^i	118.5 (10)	O1^i—S^i—O2^i	118.0 (6)
C6^i—C7^i—C2^i	122.7 (8)	O1^i—S^i—N^i	110.9 (6)
H81^i—C8^i—H82^i	107.7 (10)	O1^i—S^i—C3^i	107.3 (5)
H81^i—C8^i—C8^ii	109.2 (9)	O2^i—S^i—N^i	105.2 (5)
H81^i—C8^i—C5^i	108.3 (10)	O2^i—S^i—C3^i	110.1 (6)
H82^i—C8^i—C8^ii	109.1 (9)	N^i—S^i—C3^i	104.7 (6)
H82^i—C8^i—C5^i	108.2 (9)
H101^i—C1^i—C2^i—C3^i	160.8 (11)	C6^i—C5^i—C8^i—H82^i	38.1 (16)
H101^i—C1^i—C2^i—C7^i	−35.8 (15)	C6^i—C5^i—C8^i—C8^ii	−83.5 (13)
H102^i—C1^i—C2^i—C3^i	43.7 (15)	C5^i—C6^i—C7^i—C2^i	−3 (2)
H102^i—C1^i—C2^i—C7^i	−152.9 (11)	C5^i—C6^i—C7^i—H7^i	176.8 (12)
C1^ii—C1^i—C2^i—C3^i	−77.7 (13)	H6^i—C6^i—C7^i—C2^i	177.2 (12)
C1^ii—C1^i—C2^i—C7^i	85.7 (12)	H6^i—C6^i—C7^i—H7^i	−3 (2)
C1^i—C2^i—C3^i—C4^i	152.0 (13)	N^i—C17^i—C18^i—C19^i	180.0000
C1^i—C2^i—C3^i—S^i	−24.5 (17)	N^i—C17^i—C18^i—H181^i	59.2 (12)
C7^i—C2^i—C3^i—C4^i	−12 (2)	N^i—C17^i—C18^i—H181^ii	−59.2 (12)
C7^i—C2^i—C3^i—S^i	171.1 (10)	H171^i—C17^i—C18^i—C19^i	−59.2 (12)
C1^i—C2^i—C7^i—C6^i	−150.6 (12)	H171^i—C17^i—C18^i—H181^i	−180.0 (14)
C1^i—C2^i—C7^i—H7^i	29.2 (18)	H171^i—C17^i—C18^i—H181^ii	62 (2)
C3^i—C2^i—C7^i—C6^i	14.3 (18)	H171^ii—C17^i—C18^i—C19^i	59.2 (12)
C3^i—C2^i—C7^i—H7^i	−165.9 (12)	H171^ii—C17^i—C18^i—H181^i	−62 (2)
C2^i—C3^i—C4^i—C5^i	0 (2)	H171^ii—C17^i—C18^i—H181^ii	180.0 (14)
C2^i—C3^i—C4^i—H4^i	−179.9 (13)	C18^i—C17^i—N^i—S^i	−78.5 (9)
S^i—C3^i—C4^i—C5^i	176.0 (11)	C18^i—C17^i—N^i—S^ii	78.5 (9)
S^i—C3^i—C4^i—H4^i	−3 (2)	H171^i—C17^i—N^i—S^i	161.7 (11)
C2^i—C3^i—S^i—N^i	61.7 (12)	H171^i—C17^i—N^i—S^ii	−41 (2)
C2^i—C3^i—S^i—O1^i	179.5 (11)	H171^ii—C17^i—N^i—S^i	41 (2)
C2^i—C3^i—S^i—O2^i	−50.9 (12)	H171^ii—C17^i—N^i—S^ii	−161.7 (11)
C4^i—C3^i—S^i—N^i	−115.1 (11)	C17^i—C18^i—C19^i—H191^i	59.8 (7)
C4^i—C3^i—S^i—O1^i	2.8 (13)	C17^i—C18^i—C19^i—H192^i	180.0000
C4^i—C3^i—S^i—O2^i	132.3 (11)	C17^i—C18^i—C19^i—H191^ii	−59.8 (7)
C3^i—C4^i—C5^i—C6^i	12 (2)	H181^i—C18^i—C19^i—H191^i	−179.8 (13)
C3^i—C4^i—C5^i—C8^i	−151.8 (13)	H181^i—C18^i—C19^i—H192^i	−59.5 (14)
H4^i—C4^i—C5^i—C6^i	−168.5 (13)	H181^i—C18^i—C19^i—H191^ii	60.7 (18)
H4^i—C4^i—C5^i—C8^i	27 (2)	H181^ii—C18^i—C19^i—H191^i	−60.7 (18)
C4^i—C5^i—C6^i—C7^i	−10 (2)	H181^ii—C18^i—C19^i—H192^i	59.5 (14)
C4^i—C5^i—C6^i—H6^i	168.9 (13)	H181^ii—C18^i—C19^i—H191^ii	179.8 (13)
C8^i—C5^i—C6^i—C7^i	153.3 (12)	C17^i—N^i—S^i—C3^i	−144.0 (12)
C8^i—C5^i—C6^i—H6^i	−27 (2)	C17^i—N^i—S^i—O1^i	100.6 (12)
C4^i—C5^i—C8^i—H81^i	−41.9 (16)	C17^i—N^i—S^i—O2^i	−27.9 (13)
C4^i—C5^i—C8^i—H82^i	−158.3 (11)	S^ii—N^i—S^i—C3^i	60.7 (10)
C4^i—C5^i—C8^i—C8^ii	80.0 (13)	S^ii—N^i—S^i—O1^i	−54.7 (10)
C6^i—C5^i—C8^i—H81^i	154.6 (12)	S^ii—N^i—S^i—O2^i	176.7 (8)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1/2, −y+1/2, z−1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) x, y−1, z; (v) x, y, z−1; (vi) −x+1, −y, −z+1; (vii) −x+1/2, y−1, z; (viii) −x+1, y−1/2, −z+3/2; (ix) −x+1/2, −y+3/2, z−1/2; (x) x+1/2, −y+1, −z+1; (xi) x, y−1, z−1; (xii) −x+1/2, y−1, z−1; (xiii) −x+1, −y+1, −z+1; (xiv) x+1/2, y−1/2, −z+3/2; (xv) x, −y+3/2, z−1/2; (xvi) −x+1/2, y, z−1; (xvii) −x+1/2, y, z; (xviii) x, −y−1/2, z−1/2; (xix) −x+1/2, −y−1/2, z−1/2; (xx) x−1/2, −y, −z+1.

(PCF5) N-isopropyl-[2.2]paracyclophane-4,15-disulfonimide

Crystal data

C19H21NS2O4	F(000) = 1648
Mr = 391.5	Dx = 1.447 Mg m^−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 23 reflections
a = 12.845 (2) Å	θ = 39.9–41.8°
b = 15.0121 (7) Å	µ = 2.90 mm^−1
c = 18.6430 (8) Å	T = 293 K
V = 3594.8 (5) Å^3	Block, colourless
Z = 8	0.50 × 0.40 × 0.40 mm

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 74.7°, θmin = 4.7°
Graphite monochromator	h = 0→16
θ/2θ scans	k = 0→18
3679 measured reflections	l = 0→23
3679 independent reflections	2 standard reflections every 60 min
3190 reflections with refl observed if I > 2.5 σ(I )	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	Riding
R[F^2 > 2σ(F^2)] = 0.064	1/[6.9 + 0.0056*σ(Fobs)^2 + 0.00004/σ(Fobs)]
wR(F^2) = 0.069	(Δ/σ)max = 0.258
S = 0.98	Δρmax = 0.73 e Å^−3
3190 reflections	Δρmin = −0.89 e Å^−3
320 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
21 restraints	Extinction coefficient: 4973 (257)

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2443 (4)	0.2990 (4)	0.8075 (3)	0.051 (3)
C2	0.2138 (3)	0.3518 (3)	0.8729 (3)	0.044 (2)
C3	0.2680 (3)	0.4275 (3)	0.8978 (2)	0.036 (2)
C4	0.2661 (3)	0.4523 (3)	0.9693 (2)	0.042 (2)
C5	0.2094 (4)	0.4045 (3)	1.0191 (3)	0.050 (3)
C6	0.1379 (4)	0.3423 (4)	0.9911 (3)	0.060 (3)
C7	0.1408 (4)	0.3186 (4)	0.9207 (3)	0.059 (3)
C8	0.2391 (5)	0.4032 (4)	1.0966 (3)	0.062 (3)
C9	0.3401 (4)	0.2333 (3)	0.8230 (3)	0.049 (3)
C10	0.3746 (3)	0.2378 (3)	0.9004 (2)	0.040 (2)
C11	0.4383 (3)	0.3067 (3)	0.9282 (2)	0.034 (2)
C12	0.4354 (3)	0.3299 (3)	0.9996 (2)	0.038 (2)
C13	0.3679 (3)	0.2876 (3)	1.0465 (2)	0.044 (2)
C14	0.3225 (4)	0.2082 (3)	1.0224 (3)	0.052 (3)
C15	0.3268 (4)	0.1856 (3)	0.9512 (3)	0.054 (3)
C16	0.3302 (5)	0.3337 (5)	1.1127 (3)	0.067 (4)
C17	0.4900 (3)	0.4372 (3)	0.7384 (2)	0.044 (2)
C18	0.4240 (5)	0.4017 (4)	0.6782 (3)	0.061 (3)
C19	0.5220 (5)	0.5334 (4)	0.7281 (3)	0.062 (3)
N	0.4415 (2)	0.4190 (2)	0.8115 (2)	0.034 (2)
O1	0.2926 (2)	0.5128 (2)	0.7772 (2)	0.052 (2)
O2	0.3936 (3)	0.5611 (2)	0.8817 (2)	0.054 (2)
O4	0.5823 (3)	0.3087 (3)	0.8298 (2)	0.073 (2)
O5	0.5732 (3)	0.4347 (3)	0.9153 (2)	0.067 (2)
S1	0.34893 (7)	0.49066 (7)	0.84064 (5)	0.0360 (5)
S2	0.52109 (7)	0.36933 (8)	0.87206 (6)	0.0429 (6)
H101	0.260 (4)	0.333 (3)	0.763 (3)	0.05 (1)*
H102	0.191 (3)	0.266 (4)	0.779 (3)	0.09 (2)*
H4	0.310 (3)	0.505 (2)	0.983 (2)	0.04 (1)*
H6	0.102 (3)	0.306 (3)	1.029 (2)	0.06 (1)*
H7	0.107 (4)	0.263 (2)	0.904 (3)	0.08 (2)*
H81	0.262 (4)	0.465 (2)	1.108 (3)	0.07 (2)*
H82	0.193 (5)	0.405 (5)	1.140 (2)	0.12 (3)*
H91	0.390 (3)	0.246 (3)	0.783 (2)	0.05 (1)*
H92	0.319 (4)	0.170 (1)	0.816 (3)	0.06 (2)*
H12	0.473 (3)	0.386 (2)	1.012 (2)	0.04 (1)*
H14	0.284 (3)	0.173 (3)	1.060 (2)	0.06 (2)*
H15	0.288 (4)	0.132 (2)	0.935 (3)	0.09 (2)*
H161	0.378 (6)	0.351 (6)	1.153 (4)	0.18 (4)*
H162	0.314 (5)	0.286 (3)	1.148 (3)	0.10 (2)*
H17	0.544 (3)	0.389 (2)	0.745 (2)	0.05 (1)*
H181	0.416 (4)	0.337 (1)	0.690 (3)	0.08 (2)*
H182	0.363 (4)	0.442 (4)	0.683 (4)	0.13 (3)*
H183	0.454 (3)	0.418 (3)	0.631 (1)	0.05 (1)*
H191	0.455 (3)	0.567 (4)	0.731 (4)	0.11 (3)*
H192	0.558 (4)	0.546 (4)	0.774 (2)	0.07 (2)*
H193	0.550 (3)	0.536 (3)	0.678 (1)	0.05 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.045 (2)	0.060 (3)	0.049 (3)	−0.010 (2)	−0.024 (2)	0.002 (2)
C2	0.023 (2)	0.052 (3)	0.057 (3)	−0.001 (2)	−0.013 (2)	0.013 (2)
C3	0.021 (2)	0.039 (2)	0.049 (2)	0.006 (2)	0.004 (2)	0.010 (2)
C4	0.033 (2)	0.039 (2)	0.052 (3)	0.008 (2)	0.012 (2)	0.003 (2)
C5	0.041 (2)	0.052 (3)	0.058 (3)	0.011 (2)	0.020 (2)	0.009 (2)
C6	0.034 (2)	0.071 (3)	0.075 (4)	−0.006 (2)	0.013 (2)	0.020 (3)
C7	0.030 (2)	0.072 (4)	0.076 (4)	−0.012 (2)	−0.009 (2)	0.020 (3)
C8	0.075 (4)	0.058 (3)	0.052 (3)	0.003 (3)	0.030 (3)	0.000 (3)
C9	0.063 (3)	0.036 (2)	0.048 (3)	0.002 (2)	−0.014 (2)	−0.009 (2)
C10	0.041 (2)	0.035 (2)	0.045 (2)	0.010 (2)	−0.008 (2)	−0.002 (2)
C11	0.025 (2)	0.039 (2)	0.038 (2)	0.010 (2)	−0.005 (2)	0.003 (2)
C12	0.029 (2)	0.046 (2)	0.039 (2)	0.001 (2)	−0.009 (2)	0.003 (2)
C13	0.038 (2)	0.059 (3)	0.036 (2)	0.003 (2)	−0.007 (2)	0.009 (2)
C14	0.050 (3)	0.054 (3)	0.053 (3)	−0.008 (2)	−0.010 (2)	0.020 (2)
C15	0.061 (3)	0.037 (2)	0.064 (3)	−0.008 (2)	−0.021 (3)	0.007 (2)
C16	0.070 (4)	0.098 (5)	0.034 (2)	0.001 (3)	0.004 (2)	0.005 (3)
C17	0.036 (2)	0.065 (3)	0.031 (2)	0.010 (2)	0.004 (2)	0.001 (2)
C18	0.071 (4)	0.079 (4)	0.033 (2)	0.005 (3)	0.001 (2)	−0.006 (3)
C19	0.056 (3)	0.088 (4)	0.043 (3)	−0.022 (3)	0.010 (2)	0.009 (3)
N	0.025 (1)	0.044 (2)	0.033 (2)	0.006 (1)	0.000 (1)	0.000 (1)
O1	0.042 (2)	0.062 (2)	0.052 (2)	0.012 (2)	0.004 (1)	0.017 (2)
O2	0.055 (2)	0.042 (2)	0.066 (2)	−0.013 (2)	0.020 (2)	−0.010 (2)
O4	0.047 (2)	0.107 (3)	0.064 (2)	0.045 (2)	0.017 (2)	0.015 (2)
O5	0.046 (2)	0.096 (3)	0.059 (2)	−0.030 (2)	−0.019 (2)	0.008 (2)
S1	0.0297 (5)	0.0361 (5)	0.0422 (5)	0.0032 (4)	0.0068 (4)	0.0026 (4)
S2	0.0224 (4)	0.0661 (7)	0.0402 (6)	0.0045 (5)	−0.0021 (4)	0.0073 (5)

Geometric parameters (Å, º)

C1—H101	0.98 (5)	C12—H12	1.00 (3)
C1—H102	1.00 (5)	C12—C13	1.386 (6)
C1—C2	1.505 (7)	C13—C14	1.400 (7)
C1—C9	1.604 (7)	C13—C16	1.496 (7)
C2—C7	1.388 (7)	C14—H14	1.00 (4)
C2—C3	1.411 (6)	C14—C15	1.371 (7)
C3—C4	1.384 (6)	C15—H15	1.00 (4)
C3—S1	1.765 (4)	C16—H161	1.00 (7)
C4—H4	1.00 (3)	C16—H162	1.00 (5)
C4—C5	1.381 (7)	C17—H17	1.00 (3)
C5—C6	1.410 (7)	C17—C18	1.504 (7)
C5—C8	1.495 (7)	C17—C19	1.513 (8)
C6—H6	1.00 (4)	C17—N	1.523 (5)
C6—C7	1.360 (8)	C18—H183	1.00 (3)
C7—H7	1.00 (4)	C18—H182	1.00 (5)
C8—H82	1.00 (5)	C18—H181	1.00 (2)
C8—H81	1.00 (3)	C19—H193	1.00 (2)
C8—C16	1.597 (9)	C19—H192	1.00 (4)
C9—H92	1.00 (2)	C19—H191	1.00 (4)
C9—H91	1.00 (3)	N—S1	1.693 (3)
C9—C10	1.512 (7)	N—S2	1.697 (3)
C10—C15	1.374 (7)	O1—S1	1.426 (3)
C10—C11	1.416 (6)	O2—S1	1.426 (3)
C11—C12	1.376 (6)	O4—S2	1.438 (4)
C11—S2	1.764 (4)	O5—S2	1.435 (4)
H161···H162	1.3 (1)	C1···C15	3.347 (7)
H101···H102	1.37 (7)	C19···H82^x	3.35 (6)
H81···H82	1.39 (8)	C1···H162^viii	3.35 (5)
H182···H183	1.58 (7)	C6···C16	3.356 (8)
H191···H192	1.58 (7)	C1···C11	3.359 (6)
H91···H92	1.59 (5)	C15···H91	3.36 (3)
H191···H193	1.64 (6)	H91···H191^vi	3.36 (7)
H181···H183	1.71 (6)	C3···C9	3.363 (6)
H181···H182	1.73 (6)	N···H183	3.37 (2)
H192···H193	1.80 (4)	C18···H81^x	3.37 (5)
N···H17	1.86 (4)	C17···H101	3.38 (5)
C17···H182	1.94 (6)	C9···H7	3.38 (5)
C17···H192	1.97 (5)	S2···H6^ix	3.39 (4)
C18···H17	1.98 (4)	C4···H82	3.39 (5)
C17···H181	2.00 (4)	C7···H15	3.39 (4)
C17···H191	2.00 (6)	C5···H161	3.39 (7)
C2···H7	2.00 (4)	C7···C9	3.393 (7)
C17···H193	2.01 (4)	C19···H91^xi	3.40 (5)
C5···H81	2.01 (5)	O4···H181	3.40 (6)
C10···H92	2.01 (4)	C3···S2	3.401 (4)
C11···H12	2.02 (4)	H14···H161	3.40 (9)
C13···H162	2.02 (5)	C6···H14	3.40 (4)
C5···H6	2.02 (4)	C5···H12	3.41 (4)
C3···H4	2.03 (4)	C11···S1	3.407 (4)
C13···H14	2.04 (4)	H92···H191^vi	3.41 (6)
C10···H15	2.04 (4)	C8···H12	3.41 (4)
C14···H15	2.05 (5)	H182···H192	3.41 (7)
O4···H17	2.06 (4)	O2···H92^iii	3.41 (4)
C6···H7	2.06 (5)	H6···H12^xii	3.41 (5)
C17···H183	2.08 (3)	C8···C14	3.410 (8)
C7···H6	2.08 (4)	C14···H181^ii	3.41 (5)
C1···H91	2.08 (4)	C4···O5^i	3.430 (6)
H17···H181	2.09 (6)	S1···H17	3.43 (4)
C5···H4	2.10 (3)	C8···O5^i	3.433 (7)
C15···H14	2.10 (4)	C7···C14	3.433 (7)
C13···H12	2.10 (3)	C3···H102	3.43 (5)
C16···H82	2.12 (6)	H101···H7	3.44 (7)
C9···H101	2.13 (5)	C13···H6	3.44 (4)
C9···H102	2.14 (5)	C18···S1	3.447 (5)
C2···H101	2.15 (5)	O1···H192	3.45 (5)
H101···H91	2.15 (6)	H181···H193	3.45 (6)
C16···H81	2.16 (3)	C3···H12	3.45 (4)
C1···H92	2.17 (3)	C9···H161^viii	3.46 (7)
C10···H91	2.19 (3)	H7···H17^vii	3.46 (6)
C2···H102	2.20 (5)	C10···H7	3.46 (5)
C19···H17	2.20 (3)	C6···C15	3.460 (7)
C13···H161	2.20 (7)	C6···H183^vii	3.47 (4)
C8···H161	2.21 (7)	H81···H12	3.47 (6)
H161···H192^i	2.22 (9)	C17···O5	3.467 (5)
C8···H162	2.23 (5)	H7···H92	3.47 (7)
O1···H182	2.24 (7)	H6···H81	3.48 (6)
H91···H181	2.24 (6)	S1···H92^iii	3.48 (3)
C5···H82	2.26 (4)	C2···H183^vii	3.48 (4)
H102···H92	2.28 (6)	C17···O2	3.483 (6)
H92···H15	2.32 (7)	O1···H181	3.49 (4)
O2···H4	2.32 (4)	C16···H91^ii	3.49 (3)
H183···H193	2.33 (6)	C19···O1^v	3.491 (7)
O5···H12	2.33 (4)	C7···H17^vii	3.49 (4)
C3···C7	2.351 (7)	C18···H7^v	3.49 (4)
C11···C15	2.354 (6)	C1···H15	3.50 (5)
C4···C6	2.368 (7)	H102···H181	3.50 (7)
C12···C14	2.371 (7)	H91···H182	3.50 (8)
H82···H162	2.38 (9)	C1···H182	3.51 (6)
H14···H162	2.39 (6)	C10···H193^vi	3.51 (4)
H162···H181^ii	2.39 (6)	O5···H161^i	3.51 (9)
H182···H191	2.39 (8)	C12···O2^i	3.521 (5)
O1···H191	2.39 (5)	H12···H12^i	3.53 (4)
C11···C13	2.401 (6)	H6···H162	3.53 (7)
C13···C15	2.404 (7)	C3···H193^vii	3.54 (4)
C3···C5	2.409 (6)	H162···H182^ii	3.54 (8)
C5···C7	2.409 (8)	C16···H4	3.54 (4)
S2···H17	2.41 (5)	C11···H4	3.54 (3)
C10···C14	2.412 (7)	C13···H4	3.55 (3)
H14···H15	2.41 (7)	H183···H192	3.55 (5)
H81···H161	2.41 (9)	C7···H181^vii	3.55 (6)
C2···C6	2.415 (7)	H91···H15	3.56 (6)
H17···H192	2.42 (6)	C15···H6^ix	3.56 (4)
H6···H7	2.42 (6)	O4···H82^ix	3.56 (7)
H101···H181	2.43 (7)	H7···H161^xii	3.56 (9)
C10···C12	2.437 (6)	C8···H14	3.57 (4)
C2···C4	2.441 (6)	C7···C18^vii	3.566 (8)
O1···O2	2.450 (5)	H162···H183^ii	3.57 (7)
H17···H183	2.46 (5)	C8···H191^iv	3.57 (6)
H4···H15^iii	2.46 (5)	H181···H191	3.57 (6)
N···O1	2.460 (4)	C14···H4^xiii	3.58 (3)
O4···O5	2.476 (6)	C14···C18^ii	3.586 (7)
N···O4	2.477 (5)	O1···H15^iii	3.59 (5)
H4···H81	2.50 (7)	H12···H162	3.59 (7)
C9···C15	2.501 (7)	C9···H192^vi	3.59 (5)
C12···C16	2.506 (7)	C2···H193^vii	3.60 (4)
C18···N	2.507 (6)	C13···H6^ix	3.61 (4)
C4···C8	2.510 (7)	C9···C19^vi	3.612 (8)
C1···C7	2.512 (7)	H4···H82	3.62 (7)
H82···H161	2.5 (1)	C8···O1^iv	3.617 (6)
N···H192	2.52 (5)	C2···H15	3.62 (4)
C18···C19	2.521 (9)	C8···H192^i	3.63 (4)
H17···H193	2.52 (5)	C15···O2^xiii	3.631 (6)
C6···C8	2.529 (8)	C12···H81	3.63 (5)
C14···C16	2.529 (8)	H102···H191^xiii	3.64 (8)
H82···H182^iv	2.53 (9)	C14···H7	3.64 (5)
C19···N	2.536 (7)	C13···H183^ii	3.64 (4)
H81···H182^iv	2.54 (8)	C19···S2	3.643 (6)
C15···H92	2.54 (5)	C15···H193^vi	3.66 (4)
O4···H102^v	2.55 (5)	C17···H102^v	3.66 (5)
C5···C16	2.566 (8)	C6···C12^xii	3.670 (7)
H102···H7	2.57 (7)	S2···H14^ix	3.67 (4)
H102···H91	2.57 (6)	C1···C18	3.676 (8)
C8···C13	2.573 (7)	C5···H14	3.68 (4)
C1···H7	2.58 (5)	S2···H181	3.69 (5)
N···O2	2.577 (5)	C5···C11	3.697 (6)
C1···C10	2.578 (7)	C12···O4	3.698 (5)
C1···C3	2.578 (7)	C15···H6	3.70 (4)
C9···C11	2.579 (6)	C3···C13	3.708 (6)
C18···H193	2.58 (5)	C8···H183^iv	3.71 (4)
C2···C9	2.581 (7)	C4···O1	3.711 (5)
N···O5	2.582 (5)	C4···H7	3.71 (4)
O5···H4^i	2.58 (4)	C2···C12	3.714 (6)
H101···H182	2.59 (8)	O1···H183	3.71 (3)
C3···O2	2.592 (5)	C4···C15^iii	3.715 (6)
H82···H191^iv	2.59 (8)	C3···H6	3.72 (4)
C4···H81	2.60 (5)	O1···H17^vii	3.72 (3)
C11···O5	2.599 (5)	C6···C11^xii	3.720 (7)
C19···H182	2.60 (5)	O4···H192	3.72 (5)
N···H181	2.60 (5)	C14···H6^ix	3.72 (4)
C11···O4	2.605 (5)	C15···H12	3.72 (3)
C3···O1	2.607 (5)	C7···H4	3.73 (3)
C8···H6	2.61 (4)	O2···H12	3.73 (3)
C14···H162	2.62 (5)	C16···O5^i	3.728 (8)
N···H182	2.62 (7)	C12···H15	3.73 (4)
H92···H193^vi	2.63 (6)	C11···H14	3.73 (4)
O5···H81^i	2.63 (5)	C11···C16	3.732 (7)
C19···H183	2.65 (4)	C7···C8	3.737 (8)
C9···H15	2.66 (5)	C4···C10	3.737 (6)
C16···H14	2.67 (4)	C4···N	3.740 (5)
N···H191	2.68 (6)	S1···H181	3.74 (4)
C12···S2	2.686 (4)	C1···C6	3.743 (8)
C4···S1	2.686 (5)	C3···C8	3.744 (7)
H102···H17^vii	2.69 (6)	C9···C14	3.744 (7)
S2···H12	2.69 (4)	C15···C16	3.744 (8)
C18···H191	2.70 (6)	C7···H92	3.75 (4)
S1···H4	2.70 (4)	O5···H4	3.75 (4)
S1···H191	2.70 (6)	S2···H81^i	3.75 (4)
H17···H182	2.71 (6)	C18···O4	3.752 (7)
C17···S2	2.722 (4)	C12···N	3.755 (5)
N···H91	2.72 (5)	C5···H15^iii	3.76 (4)
C4···C7	2.728 (7)	C7···C12^xii	3.759 (7)
C12···C15	2.730 (7)	O1···H17	3.77 (3)
C3···C6	2.731 (7)	C2···C17^vii	3.769 (6)
C2···C10	2.731 (6)	C9···H191^vi	3.77 (5)
O2···H12^i	2.73 (4)	C7···C13	3.771 (7)
C5···C13	2.735 (7)	C4···H14^iii	3.78 (4)
C11···C14	2.735 (6)	O2···H102^iii	3.78 (5)
H101···H92	2.74 (6)	O5···H6^ix	3.78 (4)
C16···H12	2.74 (4)	C16···H92^ii	3.79 (5)
O2···H15^iii	2.74 (5)	O1···H161^x	3.79 (8)
H91···H162^viii	2.75 (6)	C14···H182^ii	3.79 (7)
C17···S1	2.750 (4)	C2···C14	3.791 (7)
O1···H101	2.75 (5)	C3···H91	3.80 (4)
C3···N	2.752 (5)	C6···H162	3.80 (6)
C11···N	2.753 (5)	N···H12	3.80 (4)
C8···H4	2.77 (4)	O1···H193	3.80 (4)
O4···H91	2.78 (4)	C9···C12	3.800 (6)
C2···S1	2.778 (4)	O1···H102^iii	3.80 (5)
C10···S2	2.778 (4)	C9···H17	3.80 (3)
H182···H193	2.79 (7)	C1···C4	3.804 (7)
H4···H12	2.81 (5)	C17···H101^v	3.81 (5)
H6···H82	2.81 (7)	C17···H82^x	3.81 (6)
N···H101	2.82 (5)	O2···O5^i	3.810 (5)
C11···H6^ix	2.82 (4)	C6···C10	3.816 (7)
C10···C13	2.826 (6)	C9···O1^xiii	3.819 (6)
C4···O2	2.832 (5)	C13···C18^ii	3.824 (8)
C17···O4	2.836 (6)	C7···C11	3.828 (6)
C18···H101	2.84 (5)	C6···C12	3.830 (6)
C7···H102	2.84 (5)	N···H4	3.83 (4)
C2···C5	2.839 (7)	C5···C15	3.831 (7)
C12···O5	2.842 (6)	O4···H191^vi	3.84 (6)
O1···H82^x	2.84 (5)	O1···H4	3.84 (4)
O1···H92^iii	2.85 (3)	C3···C15	3.841 (6)
H91···H161^viii	2.85 (8)	C15···H102	3.85 (5)
C4···H15^iii	2.86 (4)	C6···H15	3.85 (4)
H101···H162^viii	2.87 (7)	C19···O5	3.848 (7)
C17···O1	2.871 (5)	C16···H7^ix	3.85 (5)
H81···H162	2.88 (5)	C9···C18	3.852 (8)
C3···H101	2.89 (5)	C11···H101	3.85 (5)
O4···H101^v	2.89 (5)	O4···H12	3.85 (4)
C3···C11	2.898 (5)	C7···H14	3.85 (4)
H14···H183^ii	2.90 (6)	C18···S2	3.854 (5)
C4···C12	2.903 (6)	S1···H91	3.85 (5)
H17···H191	2.91 (7)	C16···H101^ii	3.86 (5)
H101···H17^vii	2.91 (6)	C4···C14	3.865 (7)
O2···H191	2.91 (7)	C16···H102^ii	3.87 (5)
C11···H91	2.91 (3)	C18···H161^viii	3.88 (9)
H183···H191	2.92 (7)	C12···O5^i	3.876 (6)
O2···H192	2.92 (4)	C9···S1	3.879 (5)
S1···S2	2.924 (1)	C11···H17	3.88 (4)
H12···H161	2.94 (8)	C16···O2^i	3.884 (7)
H161···H181^ii	2.95 (9)	C5···O5^i	3.888 (6)
C4···H12	2.95 (4)	S2···H102^v	3.89 (5)
H92···H192^vi	2.96 (6)	C14···H92	3.90 (5)
H14···H181^ii	2.96 (7)	C7···C13^xii	3.899 (7)
C12···H161	2.97 (7)	C1···S2	3.899 (5)
C7···H183^vii	2.98 (4)	C2···O2	3.903 (5)
S2···H91	2.99 (4)	S1···H12	3.91 (4)
H102···H162^viii	3.00 (7)	C8···C18^iv	3.908 (9)
H91···H17	3.00 (5)	C10···O5	3.914 (6)
S1···H101	3.00 (5)	C2···C13	3.915 (6)
C18···O1	3.005 (7)	C2···C18^vii	3.915 (7)
C19···H92^xi	3.01 (4)	S1···H193^vii	3.92 (4)
C12···H6^ix	3.01 (4)	C7···H193^vii	3.92 (4)
C6···H82	3.02 (5)	C14···H7^ix	3.93 (5)
S1···H182	3.03 (7)	C16···C18^ii	3.93 (1)
O2···O5	3.053 (5)	O1···H102	3.93 (5)
O2···H7^iii	3.05 (3)	C3···O5	3.936 (5)
H14···H182^ii	3.06 (8)	C5···H182^iv	3.94 (7)
C18···H14^viii	3.06 (4)	C4···S2	3.945 (4)
C1···H17^vii	3.07 (3)	C9···C17	3.946 (7)
S1···H192	3.07 (5)	C19···O4	3.948 (8)
O5···H12^i	3.08 (3)	C11···H7^ix	3.95 (5)
C18···H91	3.08 (4)	S2···H4^i	3.95 (4)
C9···N	3.085 (6)	C7···H12^xii	3.95 (3)
C9···H181	3.09 (5)	C2···S2	3.956 (4)
C12···H4	3.09 (3)	C5···C10	3.957 (6)
H7···H15	3.10 (6)	C7···O2^xiii	3.958 (7)
C19···H161^i	3.10 (8)	C11···O2	3.959 (5)
C19···O1	3.101 (7)	S2···H101	3.96 (5)
C1···N	3.109 (6)	C3···H17^vii	3.96 (4)
C8···H182^iv	3.11 (6)	S2···H4	3.96 (4)
H7···H183^vii	3.11 (6)	C1···C17^vii	3.962 (7)
O5···H192	3.12 (4)	C7···C17^vii	3.965 (7)
C19···S1	3.123 (6)	C3···H81	3.97 (5)
C16···H192^i	3.12 (4)	C10···S1	3.970 (4)
H6···H14	3.13 (6)	C15···H162	3.97 (5)
C5···C12	3.133 (6)	O5···H82^i	3.98 (6)
C2···C11	3.136 (5)	C5···H183^iv	3.98 (4)
C16···H181^ii	3.14 (4)	C12···S1	3.980 (4)
C4···C13	3.146 (6)	C16···O4^xii	3.982 (8)
C2···H17^vii	3.15 (4)	O4···H92	3.98 (4)
H92···H161^viii	3.15 (8)	C1···C17	3.991 (7)
H4···H14^iii	3.16 (5)	C5···S1	3.994 (5)
C10···O4	3.159 (6)	C13···S2	3.995 (4)
C3···C10	3.161 (6)	N···H102	4.00 (5)
O4···H6^ix	3.16 (4)	C15···S2	4.002 (5)
C6···C14	3.164 (7)	C2···H181^vii	4.00 (6)
C7···C15	3.165 (7)	C4···H161	4.00 (7)
C12···H7^ix	3.17 (5)	C8···O4^xii	4.006 (7)
C1···H181	3.17 (6)	C7···S1	4.006 (5)
C2···O1	3.170 (6)	S2···H101^v	4.01 (5)
C15···H7	3.18 (5)	C17···H7^v	4.02 (4)
H81···H192^i	3.19 (7)	S1···H12^i	4.02 (4)
C14···H6	3.19 (4)	C6···H12^xii	4.02 (3)
H92···H162^viii	3.19 (7)	C14···O5^xii	4.025 (6)
O5···H14^ix	3.19 (4)	S1···H193	4.03 (3)
C18···H162^viii	3.20 (5)	C14···H82	4.04 (6)
O1···H192^vii	3.20 (5)	C15···H183^ii	4.04 (3)
C4···C11	3.203 (6)	C6···C13^xii	4.040 (7)
H7···H181^vii	3.21 (7)	C13···O2^i	4.042 (6)
C13···H81	3.21 (4)	S2···H191	4.05 (6)
H7···H12^xii	3.22 (5)	O1···S2	4.048 (3)
C3···C12	3.222 (6)	C16···C19^i	4.048 (8)
C3···H15^iii	3.22 (4)	C9···C16^viii	4.048 (7)
C9···S2	3.227 (5)	C17···O1^v	4.059 (5)
H4···H12^i	3.23 (5)	O4···S1	4.061 (4)
C2···H92	3.23 (3)	C7···C12	4.064 (6)
C2···H91	3.23 (4)	C6···C11	4.068 (6)
C3···H7	3.23 (4)	C4···O5	4.080 (5)
C4···H6	3.23 (4)	C3···C14	4.090 (7)
C1···S1	3.235 (5)	S1···H82^x	4.09 (5)
C6···C13	3.235 (7)	C4···C15	4.094 (6)
C2···C15	3.236 (7)	C6···O4^xii	4.097 (7)
O1···H81^x	3.24 (5)	C11···C17	4.100 (6)
C12···H14	3.25 (4)	S2···H92	4.10 (4)
O1···H193^vii	3.25 (4)	S1···H102	4.10 (5)
C14···H183^ii	3.25 (4)	C9···O2^xiii	4.109 (6)
C17···H91	3.25 (4)	C10···C19^vi	4.113 (8)
C12···H162	3.25 (5)	C6···C10^xii	4.120 (7)
S2···H192	3.25 (5)	C3···C17	4.122 (6)
C7···C10	3.261 (6)	C4···C14^iii	4.127 (7)
C11···H15	3.26 (4)	C2···C19^vii	4.128 (8)
S1···H15^iii	3.26 (5)	C6···C14^xii	4.129 (7)
H82···H183^iv	3.26 (8)	C14···O4^xii	4.143 (6)
H91···H192^vi	3.27 (7)	C12···O2	4.144 (5)
C6···H81	3.27 (5)	C16···O1^iv	4.146 (7)
O5···H17	3.27 (5)	C6···C15^xii	4.159 (7)
C10···H101	3.27 (5)	O5···O5^i	4.167 (5)
C10···H6^ix	3.28 (4)	C3···C15^iii	4.181 (6)
O2···H161^i	3.28 (8)	C2···O4^vii	4.190 (6)
C5···H162	3.28 (5)	C5···O2	4.206 (6)
H161···H191^i	3.29 (9)	S2···H182	4.21 (7)
C5···C14	3.285 (7)	C1···O2^xiii	4.220 (6)
C9···H193^vi	3.29 (5)	C13···O5	4.221 (6)
C9···H162^viii	3.29 (5)	C15···S1^xiii	4.231 (5)
C15···H4^xiii	3.29 (3)	S1···H161^i	4.24 (8)
C10···H102	3.29 (5)	C7···C14^xii	4.243 (7)
C8···C12	3.294 (7)	C3···C19^vii	4.245 (7)
C13···H7^ix	3.29 (5)	C10···C16	4.251 (7)
H15···H193^vi	3.30 (6)	C2···C8	4.255 (7)
C18···H192	3.30 (5)	C8···C19^iv	4.261 (8)
C13···H15	3.30 (5)	C9···C13	4.261 (6)
C2···N	3.299 (5)	S2···H12^i	4.26 (3)
C6···H4	3.30 (3)	C7···C11^xii	4.271 (7)
C10···H12	3.30 (3)	C1···C5	4.274 (7)
C10···N	3.300 (5)	C6···C18^vii	4.280 (8)
C5···H7	3.30 (4)	S1···H183	4.28 (3)
C14···H12	3.30 (3)	C1···C16^viii	4.286 (8)
C1···O4^vii	3.302 (6)	S1···H7^iii	4.29 (3)
H81···H14^iii	3.31 (5)	C13···O5^i	4.297 (6)
O5···S1	3.308 (4)	C8···C11	4.302 (7)
H81···H183^iv	3.31 (6)	C3···C16	4.323 (7)
C2···H6	3.31 (4)	C9···O1	4.326 (6)
C11···H92	3.31 (4)	C7···C16	4.335 (8)
C9···O4	3.314 (6)	C6···S2^xii	4.342 (6)
C7···H101	3.32 (5)	C1···C14	4.350 (7)
C2···H4	3.32 (4)	C1···O1^xiii	4.359 (6)
C4···C16	3.317 (7)	C10···O2^xiii	4.362 (5)
O2···S2	3.317 (3)	C1···O4	4.364 (6)
C1···O1	3.318 (6)	C1···C12	4.367 (6)
C13···H181^ii	3.32 (5)	C4···C9	4.377 (6)
O4···H162^ix	3.32 (6)	C3···C17^vii	4.383 (6)
C14···H161	3.32 (8)	C6···C9	4.387 (7)
H82···H193^iv	3.32 (7)	C9···S1^xiii	4.390 (5)
C19···H181	3.33 (3)	C8···C15	4.392 (8)
O4···H14^ix	3.33 (4)	C15···O4	4.394 (6)
C10···H14	3.33 (4)	C1···C18^vii	4.402 (8)
C19···O2	3.330 (6)	C5···C15^iii	4.430 (7)
H91···H193^vi	3.33 (6)	C19···S1^v	4.437 (6)
N···H193	3.34 (3)	C6···S1	4.492 (6)
C18···H82^x	3.34 (7)	C14···S2^xii	4.496 (5)
C13···H82	3.34 (6)	C14···S2	4.496 (5)
H162···H192^i	3.35 (7)	C1···S2^vii	4.532 (5)
C16···H6	3.35 (4)	C8···S2^i	4.636 (6)
H101—C1—H102	87 (4)	C14—C13—C16	121.6 (4)
H101—C1—C2	117 (3)	H14—C14—C15	124 (2)
H101—C1—C9	108 (3)	H14—C14—C13	115 (2)
H102—C1—C2	121 (3)	C15—C14—C13	120.3 (5)
H102—C1—C9	108 (3)	H15—C15—C14	119 (3)
C2—C1—C9	112.2 (4)	H15—C15—C10	118 (3)
C7—C2—C3	114.3 (4)	C14—C15—C10	122.9 (5)
C7—C2—C1	120.5 (4)	H161—C16—H162	80 (6)
C3—C2—C1	124.2 (4)	H161—C16—C13	123 (4)
C4—C3—C2	121.7 (4)	H161—C16—C8	115 (5)
C4—C3—S1	116.6 (3)	H162—C16—C13	106 (3)
C2—C3—S1	121.6 (3)	H162—C16—C8	116 (3)
H4—C4—C5	123 (2)	C13—C16—C8	112.6 (4)
H4—C4—C3	116 (2)	H17—C17—C18	103 (2)
C5—C4—C3	121.1 (4)	H17—C17—C19	121 (2)
C4—C5—C6	116.0 (5)	H17—C17—N	93 (3)
C4—C5—C8	121.5 (4)	C18—C17—C19	113.4 (4)
C6—C5—C8	121.0 (5)	C18—C17—N	111.9 (4)
H6—C6—C7	123 (2)	C19—C17—N	113.3 (4)
H6—C6—C5	113 (2)	H183—C18—H182	104 (5)
C7—C6—C5	120.8 (5)	H183—C18—H181	118 (4)
H7—C7—C6	121 (3)	H183—C18—C17	111 (2)
H7—C7—C2	113 (3)	H182—C18—H181	120 (5)
C6—C7—C2	123.0 (5)	H182—C18—C17	99 (4)
H82—C8—H81	88 (5)	H181—C18—C17	104 (3)
H82—C8—C5	129 (3)	H193—C19—H192	129 (4)
H82—C8—C16	107 (4)	H193—C19—H191	111 (5)
H81—C8—C5	106 (3)	H193—C19—C17	104 (3)
H81—C8—C16	111 (3)	H192—C19—H191	105 (5)
C5—C8—C16	112.2 (4)	H192—C19—C17	101 (3)
H92—C9—H91	105 (4)	H191—C19—C17	104 (3)
H92—C9—C10	105 (3)	C17—N—S1	117.4 (3)
H92—C9—C1	111 (3)	C17—N—S2	115.4 (2)
H91—C9—C10	120 (2)	S1—N—S2	119.2 (2)
H91—C9—C1	104 (2)	O2—S1—O1	118.4 (2)
C10—C9—C1	111.7 (4)	O2—S1—N	111.1 (2)
C15—C10—C11	115.0 (4)	O2—S1—C3	108.2 (2)
C15—C10—C9	120.1 (4)	O1—S1—N	103.8 (2)
C11—C10—C9	123.4 (4)	O1—S1—C3	109.1 (2)
C12—C11—C10	121.5 (4)	N—S1—C3	105.5 (2)
C12—C11—S2	117.0 (3)	O5—S2—O4	119.0 (2)
C10—C11—S2	121.4 (3)	O5—S2—N	110.8 (2)
H12—C12—C11	115 (2)	O5—S2—C11	108.2 (2)
H12—C12—C13	123 (2)	O4—S2—N	104.1 (2)
C11—C12—C13	120.7 (4)	O4—S2—C11	108.5 (2)
C12—C13—C14	116.6 (4)	N—S2—C11	105.4 (2)
C12—C13—C16	120.8 (5)
C9—C1—C2—C3	78.4 (6)	C15—C10—C11—S2	170.2 (3)
C9—C1—C2—C7	−89.3 (5)	C9—C10—C15—C14	−153.7 (5)
H101—C1—C2—C3	−48 (3)	C9—C10—C15—H15	20 (3)
H101—C1—C2—C7	145 (3)	C11—C10—C15—C14	13.0 (7)
H102—C1—C2—C3	−152 (4)	C11—C10—C15—H15	−173 (3)
H102—C1—C2—C7	40 (4)	C10—C11—C12—C13	−1.6 (6)
C2—C1—C9—C10	1.9 (6)	C10—C11—C12—H12	−170 (2)
C2—C1—C9—H91	−129 (2)	S2—C11—C12—C13	176.1 (3)
C2—C1—C9—H92	118 (3)	S2—C11—C12—H12	8 (2)
H101—C1—C9—C10	133 (3)	C10—C11—S2—N	60.2 (4)
H101—C1—C9—H91	2 (4)	C10—C11—S2—O4	−50.8 (4)
H101—C1—C9—H92	−111 (4)	C10—C11—S2—O5	178.8 (3)
H102—C1—C9—C10	−134 (3)	C12—C11—S2—N	−117.5 (3)
H102—C1—C9—H91	94 (4)	C12—C11—S2—O4	131.5 (3)
H102—C1—C9—H92	−18 (4)	C12—C11—S2—O5	1.1 (4)
C1—C2—C3—C4	−153.6 (4)	C11—C12—C13—C14	14.8 (6)
C1—C2—C3—S1	21.8 (6)	C11—C12—C13—C16	−153.8 (4)
C7—C2—C3—C4	14.8 (6)	H12—C12—C13—C14	−178 (2)
C7—C2—C3—S1	−169.9 (3)	H12—C12—C13—C16	13 (2)
C1—C2—C7—C6	154.0 (5)	C12—C13—C14—C15	−14.2 (7)
C1—C2—C7—H7	−7 (3)	C12—C13—C14—H14	170 (3)
C3—C2—C7—C6	−14.8 (7)	C16—C13—C14—C15	154.3 (5)
C3—C2—C7—H7	−176 (3)	C16—C13—C14—H14	−22 (3)
C2—C3—C4—C5	−1.1 (6)	C12—C13—C16—C8	78.7 (6)
C2—C3—C4—H4	176 (2)	C12—C13—C16—H161	−65 (6)
S1—C3—C4—C5	−176.7 (3)	C12—C13—C16—H162	−153 (4)
S1—C3—C4—H4	0 (2)	C14—C13—C16—C8	−89.2 (6)
C2—C3—S1—N	−60.0 (4)	C14—C13—C16—H161	128 (6)
C2—C3—S1—O1	51.0 (4)	C14—C13—C16—H162	39 (4)
C2—C3—S1—O2	−179.0 (3)	C13—C14—C15—C10	0.0 (8)
C4—C3—S1—N	115.6 (3)	C13—C14—C15—H15	−174 (3)
C4—C3—S1—O1	−133.4 (3)	H14—C14—C15—C10	176 (3)
C4—C3—S1—O2	−3.4 (4)	H14—C14—C15—H15	2 (4)
C3—C4—C5—C6	−12.9 (7)	C19—C17—C18—H181	174 (3)
C3—C4—C5—C8	153.5 (5)	C19—C17—C18—H182	−63 (4)
H4—C4—C5—C6	170 (2)	C19—C17—C18—H183	46 (3)
H4—C4—C5—C8	−24 (2)	N—C17—C18—H181	−57 (3)
C4—C5—C6—C7	13.0 (7)	N—C17—C18—H182	67 (4)
C4—C5—C6—H6	176 (3)	N—C17—C18—H183	176 (3)
C8—C5—C6—C7	−153.5 (5)	H17—C17—C18—H181	42 (4)
C8—C5—C6—H6	10 (3)	H17—C17—C18—H182	165 (4)
C4—C5—C8—C16	−81.5 (6)	H17—C17—C18—H183	−86 (4)
C4—C5—C8—H81	39 (3)	C18—C17—C19—H191	66 (4)
C4—C5—C8—H82	140 (6)	C18—C17—C19—H192	175 (3)
C6—C5—C8—C16	84.3 (6)	C18—C17—C19—H193	−49 (3)
C6—C5—C8—H81	−155 (3)	N—C17—C19—H191	−62 (4)
C6—C5—C8—H82	−54 (6)	N—C17—C19—H192	46 (3)
C5—C6—C7—C2	1.2 (8)	N—C17—C19—H193	−178 (3)
C5—C6—C7—H7	161 (3)	H17—C17—C19—H191	−171 (5)
H6—C6—C7—C2	−160 (3)	H17—C17—C19—H192	−62 (4)
H6—C6—C7—H7	0 (4)	H17—C17—C19—H193	73 (4)
C5—C8—C16—C13	1.8 (7)	C18—C17—N—S1	−82.8 (5)
C5—C8—C16—H161	148 (5)	C18—C17—N—S2	128.4 (4)
C5—C8—C16—H162	−121 (3)	C19—C17—N—S1	46.9 (5)
H81—C8—C16—C13	−116 (3)	C19—C17—N—S2	−101.9 (4)
H81—C8—C16—H161	30 (6)	H17—C17—N—S1	172 (2)
H81—C8—C16—H162	121 (5)	H17—C17—N—S2	23 (2)
H82—C8—C16—C13	149 (4)	C17—N—S1—C3	151.9 (3)
H82—C8—C16—H161	−64 (6)	C17—N—S1—O1	37.2 (3)
H82—C8—C16—H162	26 (5)	C17—N—S1—O2	−91.1 (3)
C1—C9—C10—C11	−79.3 (5)	S2—N—S1—C3	−60.5 (3)
C1—C9—C10—C15	86.2 (5)	S2—N—S1—O1	−175.2 (2)
H91—C9—C10—C11	43 (3)	S2—N—S1—O2	56.5 (3)
H91—C9—C10—C15	−152 (3)	C17—N—S2—C11	−150.6 (3)
H92—C9—C10—C11	161 (3)	C17—N—S2—O4	−36.5 (3)
H92—C9—C10—C15	−34 (3)	C17—N—S2—O5	92.5 (3)
C9—C10—C11—C12	154.0 (4)	S1—N—S2—C11	61.2 (3)
C9—C10—C11—S2	−23.6 (6)	S1—N—S2—O4	175.3 (2)
C15—C10—C11—C12	−12.2 (6)	S1—N—S2—O5	−55.7 (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, y−1/2, −z+3/2; (vii) x−1/2, y, −z+3/2; (viii) x, −y+1/2, z−1/2; (ix) x+1/2, −y+1/2, −z+2; (x) −x+1/2, −y+1, z−1/2; (xi) −x+1, y+1/2, −z+3/2; (xii) x−1/2, −y+1/2, −z+2; (xiii) −x+1/2, y−1/2, z.

(PCF6) N-cyclopropyl-[2.2]paracyclophane-4,15-disulfonimide

Crystal data

C19H19NS2O4	F(000) = 1632
Mr = 389.5	Dx = 1.51 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 23 reflections
a = 9.826 (2) Å	θ = 20.0–20.9°
b = 14.632 (2) Å	µ = 0.34 mm^−1
c = 23.770 (4) Å	T = 293 K
V = 3418 (1) Å^3	Block, colourless
Z = 8	0.50 × 0.45 × 0.40 mm

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 29.9°, θmin = 1.7°
Graphite monochromator	h = 0→13
θ/2θ scans	k = 0→20
4940 measured reflections	l = 0→33
4940 independent reflections	2 standard reflections every 60 min
3089 reflections with refl observed if I > 2.5 σ(I )	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	Riding
R[F^2 > 2σ(F^2)] = 0.046	1/[6.2 + 0.0085*σ(Fobs)^2 + 0.00009/σ(Fobs)]
wR(F^2) = 0.052	(Δ/σ)max = 0.205
S = 0.77	Δρmax = 0.29 e Å^−3
3089 reflections	Δρmin = −0.39 e Å^−3
312 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
19 restraints	Extinction coefficient: 17781 (506)

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5051 (4)	0.2877 (3)	0.6928 (2)	0.043 (2)
C2	0.5296 (3)	0.2754 (2)	0.6314 (1)	0.033 (2)
C3	0.4832 (3)	0.3369 (2)	0.5898 (1)	0.029 (1)
C4	0.5486 (3)	0.3466 (2)	0.5381 (1)	0.032 (2)
C5	0.6651 (3)	0.2953 (2)	0.5261 (1)	0.036 (2)
C6	0.6911 (4)	0.2215 (2)	0.5608 (2)	0.042 (2)
C7	0.6246 (4)	0.2114 (2)	0.6119 (2)	0.042 (2)
C8	0.7694 (4)	0.3311 (3)	0.4849 (2)	0.049 (2)
C9	0.6021 (4)	0.3628 (3)	0.7199 (2)	0.042 (2)
C10	0.7053 (3)	0.3985 (2)	0.6789 (1)	0.037 (2)
C11	0.6772 (3)	0.4658 (2)	0.6373 (1)	0.033 (2)
C12	0.7485 (3)	0.4716 (2)	0.5873 (1)	0.036 (2)
C13	0.8515 (3)	0.4093 (3)	0.5756 (2)	0.043 (2)
C14	0.8982 (4)	0.3552 (3)	0.6196 (2)	0.051 (2)
C15	0.8265 (4)	0.3498 (3)	0.6696 (2)	0.048 (2)
C16	0.8858 (4)	0.3876 (3)	0.5150 (2)	0.053 (2)
C17	0.2930 (4)	0.5214 (2)	0.6890 (1)	0.037 (2)
C18	0.1581 (4)	0.5521 (3)	0.6663 (2)	0.052 (2)
C19	0.2567 (5)	0.6209 (3)	0.6865 (2)	0.056 (3)
N	0.3981 (3)	0.4842 (2)	0.6512 (1)	0.033 (1)
O1	0.3121 (3)	0.4557 (2)	0.5512 (1)	0.052 (2)
O2	0.2377 (2)	0.3587 (2)	0.6299 (1)	0.052 (2)
O4	0.5368 (3)	0.6014 (2)	0.5969 (1)	0.046 (1)
O5	0.5569 (3)	0.5886 (2)	0.7002 (1)	0.051 (2)
S1	0.34359 (8)	0.40874 (5)	0.60215 (4)	0.0340 (4)
S2	0.54288 (8)	0.54553 (5)	0.64612 (4)	0.0334 (4)
H101	0.520 (4)	0.230 (2)	0.714 (2)	0.07 (1)*
H102	0.411 (2)	0.308 (3)	0.702 (2)	0.07 (1)*
H4	0.523 (3)	0.395 (2)	0.511 (1)	0.029 (9)*
H6	0.770 (2)	0.182 (2)	0.550 (1)	0.033 (9)*
H7	0.659 (3)	0.168 (2)	0.641 (1)	0.035 (9)*
H81	0.809 (3)	0.281 (2)	0.462 (1)	0.05 (1)*
H82	0.720 (4)	0.369 (2)	0.457 (1)	0.06 (1)*
H91	0.645 (4)	0.337 (3)	0.754 (1)	0.08 (2)*
H92	0.541 (4)	0.413 (2)	0.732 (2)	0.07 (1)*
H12	0.718 (4)	0.518 (2)	0.560 (1)	0.05 (1)*
H14	0.975 (3)	0.313 (2)	0.611 (2)	0.05 (1)*
H15	0.857 (4)	0.309 (2)	0.700 (1)	0.07 (1)*
H161	0.971 (3)	0.351 (3)	0.514 (2)	0.09 (2)*
H162	0.899 (4)	0.449 (2)	0.497 (2)	0.07 (1)*
H17	0.299 (4)	0.495 (2)	0.7276 (7)	0.04 (1)*
H181	0.146 (4)	0.550 (3)	0.6241 (5)	0.05 (1)*
H182	0.081 (3)	0.534 (2)	0.691 (1)	0.05 (1)*
H191	0.243 (5)	0.645 (3)	0.7255 (8)	0.07 (1)*
H192	0.302 (3)	0.659 (2)	0.657 (1)	0.05 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.046 (2)	0.038 (2)	0.046 (2)	−0.008 (2)	−0.000 (2)	0.008 (2)
C2	0.030 (2)	0.027 (1)	0.043 (2)	−0.005 (1)	−0.006 (1)	−0.001 (1)
C3	0.024 (1)	0.023 (1)	0.040 (2)	−0.000 (1)	−0.004 (1)	−0.006 (1)
C4	0.034 (2)	0.028 (1)	0.033 (2)	0.003 (1)	−0.004 (1)	−0.006 (1)
C5	0.036 (2)	0.030 (1)	0.041 (2)	0.007 (1)	−0.002 (1)	−0.010 (1)
C6	0.038 (2)	0.031 (2)	0.056 (2)	0.011 (1)	−0.002 (2)	−0.010 (2)
C7	0.042 (2)	0.025 (1)	0.058 (3)	0.003 (1)	−0.013 (2)	0.003 (1)
C8	0.051 (2)	0.047 (2)	0.049 (2)	0.010 (2)	0.017 (2)	−0.007 (2)
C9	0.053 (2)	0.043 (2)	0.030 (2)	−0.008 (2)	−0.004 (2)	0.001 (1)
C10	0.038 (2)	0.039 (2)	0.034 (2)	−0.009 (1)	−0.013 (1)	−0.002 (1)
C11	0.027 (1)	0.032 (2)	0.040 (2)	−0.007 (1)	−0.002 (1)	−0.005 (1)
C12	0.030 (1)	0.031 (2)	0.047 (2)	−0.004 (1)	0.004 (1)	0.000 (1)
C13	0.027 (1)	0.046 (2)	0.055 (2)	−0.004 (2)	0.004 (1)	−0.001 (2)
C14	0.027 (2)	0.055 (2)	0.071 (3)	0.004 (2)	−0.010 (2)	−0.009 (2)
C15	0.041 (2)	0.051 (2)	0.053 (2)	0.000 (2)	−0.021 (2)	0.004 (2)
C16	0.037 (2)	0.057 (3)	0.066 (3)	0.007 (2)	0.017 (2)	−0.001 (2)
C17	0.043 (2)	0.037 (2)	0.033 (2)	0.005 (1)	0.014 (1)	0.001 (1)
C18	0.042 (2)	0.055 (2)	0.059 (3)	0.014 (2)	0.015 (2)	0.006 (2)
C19	0.065 (3)	0.039 (2)	0.066 (3)	0.013 (2)	0.024 (2)	−0.001 (2)
N	0.029 (1)	0.030 (1)	0.042 (2)	−0.003 (1)	0.008 (1)	−0.006 (1)
O1	0.050 (2)	0.051 (2)	0.054 (2)	0.022 (1)	−0.014 (1)	−0.005 (1)
O2	0.028 (1)	0.044 (1)	0.085 (2)	−0.009 (1)	0.008 (1)	−0.012 (1)
O4	0.044 (1)	0.038 (1)	0.056 (2)	−0.001 (1)	0.008 (1)	0.013 (1)
O5	0.057 (2)	0.044 (1)	0.052 (2)	−0.004 (1)	−0.002 (1)	−0.020 (1)
S1	0.0246 (3)	0.0315 (4)	0.0458 (5)	0.0021 (3)	−0.0028 (3)	−0.0067 (3)
S2	0.0339 (4)	0.0267 (3)	0.0398 (4)	−0.0050 (3)	0.0030 (4)	−0.0035 (3)

Geometric parameters (Å, º)

C1—H101	1.00 (3)	C12—H12	0.99 (3)
C1—H102	1.00 (2)	C12—C13	1.390 (5)
C1—C2	1.491 (5)	C13—C14	1.389 (6)
C1—C9	1.592 (6)	C13—C16	1.515 (6)
C2—C7	1.401 (5)	C14—H14	1.00 (3)
C2—C3	1.412 (4)	C14—C15	1.384 (6)
C3—C4	1.395 (5)	C15—H15	1.00 (3)
C3—S1	1.753 (3)	C16—H162	1.00 (3)
C4—H4	0.99 (2)	C16—H161	1.00 (3)
C4—C5	1.397 (5)	C17—H17	1.00 (2)
C5—C6	1.383 (5)	C17—N	1.473 (4)
C5—C8	1.512 (5)	C17—C18	1.500 (6)
C6—H6	1.00 (2)	C17—C19	1.501 (5)
C6—C7	1.387 (6)	C18—H182	1.00 (3)
C7—H7	1.00 (3)	C18—H181	1.01 (1)
C8—H82	1.00 (3)	C18—C19	1.478 (6)
C8—H81	1.00 (3)	C19—H191	1.00 (2)
C8—C16	1.582 (6)	C19—H192	1.00 (3)
C9—H92	1.00 (3)	N—S2	1.686 (3)
C9—H91	1.00 (3)	N—S1	1.693 (3)
C9—C10	1.501 (5)	O1—S1	1.426 (3)
C10—C15	1.405 (5)	O2—S1	1.433 (3)
C10—C11	1.421 (5)	O4—S2	1.428 (3)
C11—C12	1.382 (5)	O5—S2	1.438 (3)
C11—S2	1.774 (3)
H81···H82	1.56 (5)	C18···O5^i	3.369 (5)
H101···H102	1.60 (5)	C1···C11	3.375 (5)
H91···H92	1.61 (5)	C11···H7^iv	3.38 (3)
H161···H162	1.65 (5)	C11···H91	3.38 (3)
H181···H182	1.74 (4)	H91···H192^xi	3.38 (5)
H191···H192	1.74 (4)	C3···S2	3.385 (3)
C13···H162	2.01 (4)	H4···H81^viii	3.39 (4)
C5···H6	2.03 (3)	C16···O1^vi	3.393 (5)
C2···H7	2.03 (3)	C7···C9	3.399 (5)
C11···H12	2.03 (3)	C5···H12	3.40 (3)
C13···H14	2.04 (3)	O4···S1	3.401 (3)
C5···H82	2.05 (3)	C4···O4^vi	3.403 (4)
C5···H4	2.06 (3)	C4···C16	3.411 (5)
C10···H15	2.06 (4)	C19···H82^vi	3.41 (3)
C13···H161	2.06 (4)	C7···H15	3.42 (4)
C17···H191	2.06 (4)	C17···O1	3.419 (4)
C10···H92	2.06 (4)	C7···C14	3.419 (5)
N···H17	2.07 (2)	H17···H182^v	3.43 (4)
C14···H15	2.08 (3)	C18···O1	3.429 (5)
C2···H101	2.08 (4)	H14···H162	3.44 (5)
C15···H14	2.09 (3)	S2···H7^iv	3.44 (3)
C6···H7	2.09 (3)	C16···H181^vi	3.44 (2)
C9···H102	2.09 (3)	C8···H192^vi	3.45 (3)
C17···H182	2.09 (3)	C17···O4	3.449 (4)
C2···H102	2.09 (4)	C7···H12^ii	3.45 (3)
C5···H81	2.10 (3)	C9···H7	3.45 (3)
C3···H4	2.10 (3)	C11···H17^v	3.45 (2)
C1···H92	2.10 (3)	O1···S2	3.458 (3)
C7···H6	2.10 (3)	C6···C15	3.460 (6)
C10···H91	2.10 (3)	C8···C14	3.461 (6)
C13···H12	2.10 (3)	C12···H82	3.46 (3)
C19···H181	2.11 (3)	C4···H6^viii	3.47 (3)
C9···H101	2.11 (3)	C13···H6	3.47 (3)
C18···H192	2.12 (3)	O1···H81^viii	3.48 (3)
C8···H161	2.12 (3)	H4···H81	3.48 (4)
C18···H191	2.12 (4)	H7···H181^ix	3.48 (5)
C19···H17	2.12 (3)	C1···H15	3.48 (4)
H102···H92	2.13 (5)	C7···H161^viii	3.48 (5)
C1···H91	2.14 (4)	C17···H92^i	3.48 (4)
C16···H81	2.15 (3)	C11···S1	3.485 (3)
C19···H182	2.15 (3)	H102···H7	3.49 (4)
C17···H192	2.15 (3)	C19···O4	3.492 (6)
C17···H181	2.16 (3)	C12···O1^vi	3.511 (5)
C16···H82	2.16 (3)	C10···H7	3.52 (3)
C8···H162	2.16 (3)	C6···H161	3.52 (4)
C18···H17	2.17 (3)	C11···H4	3.52 (3)
H101···H91	2.21 (5)	H101···H15	3.53 (6)
H17···H191	2.25 (5)	N···H82^vi	3.54 (3)
H81···H161	2.27 (5)	C1···C19^ix	3.549 (6)
H82···H162	2.32 (5)	H92···H15	3.55 (5)
O4···H12	2.33 (3)	H6···H82	3.55 (4)
H181···H192	2.34 (5)	S2···H6^iv	3.56 (3)
H4···H82	2.36 (5)	C9···H17	3.56 (3)
C3···C7	2.362 (4)	C7···H81^viii	3.56 (3)
H14···H161	2.36 (6)	C7···H181^ix	3.56 (4)
C4···C6	2.367 (5)	C16···H4	3.57 (3)
C11···C15	2.370 (5)	C13···H4	3.58 (3)
H17···H182	2.37 (4)	C19···H91^x	3.58 (4)
C12···C14	2.377 (5)	C3···H12	3.59 (3)
H101···H7	2.38 (5)	S1···H82^vi	3.59 (3)
H102···H15^i	2.39 (5)	C18···H7^xii	3.60 (3)
C11···C13	2.401 (5)	C19···H101^x	3.60 (4)
H182···H191	2.41 (5)	H101···H192^ix	3.60 (5)
C13···C15	2.409 (6)	C14···H182^xiii	3.61 (3)
C5···C7	2.414 (5)	C3···H92	3.61 (4)
H6···H12^ii	2.42 (4)	C15···H91^v	3.62 (4)
H14···H15	2.42 (5)	H91···H14^i	3.62 (5)
C3···C5	2.419 (5)	C8···H14	3.63 (3)
C2···C6	2.440 (5)	C5···C11	3.636 (5)
H6···H7	2.44 (4)	C15···H101	3.64 (4)
C10···C14	2.445 (5)	O4···H4	3.65 (2)
O1···H4	2.45 (3)	C17···O5^i	3.645 (4)
C2···C4	2.458 (5)	C14···H7	3.65 (3)
O1···O2	2.459 (4)	C13···H162^iii	3.65 (4)
C10···C12	2.461 (5)	C2···H15	3.65 (4)
O4···O5	2.469 (4)	C9···H102^v	3.65 (3)
N···O2	2.473 (4)	S1···H92	3.65 (4)
N···O5	2.474 (4)	C1···H192^ix	3.66 (3)
H91···H15	2.48 (6)	C5···H14	3.66 (3)
H162···H162^iii	2.49 (5)	C4···N	3.671 (4)
O4···H6^iv	2.50 (3)	C18···H91^i	3.68 (4)
C12···C16	2.508 (6)	C5···H81^viii	3.68 (3)
C1···C7	2.514 (6)	C9···C17^v	3.686 (5)
C9···C15	2.516 (6)	C3···C8^viii	3.689 (5)
O2···H102	2.52 (3)	C12···O5	3.698 (4)
C4···C8	2.520 (5)	C3···H161^viii	3.70 (5)
C6···C8	2.534 (6)	C7···O4^ii	3.713 (4)
C14···C16	2.535 (7)	C8···O4^vi	3.716 (5)
H12···H162	2.54 (5)	C15···H182^xiii	3.72 (3)
N···O4	2.542 (4)	C10···C17^v	3.720 (5)
N···O1	2.557 (4)	C2···H181^ix	3.72 (4)
H92···H182^v	2.56 (5)	C10···H102^v	3.73 (4)
C1···C3	2.562 (5)	C2···H192^ix	3.73 (3)
C2···C9	2.564 (5)	C19···O2^xii	3.730 (5)
C5···C16	2.569 (5)	C3···H6	3.73 (2)
H6···H81	2.57 (4)	C11···H14	3.74 (3)
C1···C10	2.571 (5)	C2···C12	3.736 (5)
C8···C13	2.571 (6)	C11···C16	3.737 (6)
C19···N	2.577 (5)	C13···H181^xiii	3.74 (4)
C9···C11	2.582 (5)	C4···H7	3.74 (3)
C18···N	2.583 (5)	C7···H4	3.74 (2)
C3···O1	2.587 (4)	C1···H17	3.74 (3)
C4···H82	2.59 (3)	C15···H12	3.74 (3)
O1···H82^vi	2.59 (4)	C12···H15	3.75 (3)
N···H92	2.60 (4)	C7···H14	3.75 (3)
C11···O4	2.601 (4)	C7···C13	3.755 (5)
C14···H161	2.60 (5)	C6···C12	3.755 (5)
H82···H181^vi	2.61 (4)	C14···H181^xiii	3.76 (4)
C3···O2	2.613 (4)	C1···C6	3.758 (6)
C1···H7	2.61 (3)	C6···C12^ii	3.758 (5)
C11···O5	2.620 (4)	C3···C8	3.759 (5)
C12···H162	2.63 (4)	C4···O2	3.759 (4)
O4···H4^vi	2.63 (3)	C4···C10	3.761 (5)
C7···H101	2.65 (4)	C15···C16	3.762 (6)
H102···H91	2.66 (5)	C9···C14	3.764 (6)
H92···H17	2.67 (5)	C12···N	3.767 (4)
C8···H6	2.67 (3)	C9···H191^xi	3.77 (4)
C8···H4	2.67 (3)	S2···H82^vi	3.77 (3)
C9···H15	2.67 (4)	C7···C12^ii	3.769 (5)
O5···H191^v	2.67 (4)	C7···C8	3.770 (6)
O5···H92	2.68 (3)	C9···C15^i	3.778 (6)
C16···H14	2.68 (3)	C1···H191^xi	3.78 (4)
C17···S2	2.682 (4)	N···H4	3.78 (3)
O1···H12^vi	2.68 (3)	S2···H191	3.79 (4)
C12···S2	2.684 (4)	C3···C13	3.786 (4)
C4···S1	2.685 (3)	O1···H161^vii	3.79 (3)
C17···S1	2.688 (4)	C15···H101^v	3.79 (4)
C15···H91	2.70 (4)	C6···H81^viii	3.79 (3)
O2···H14^vii	2.70 (3)	C7···H182^ix	3.79 (3)
S2···H12	2.71 (3)	C19···S1	3.794 (4)
O5···H182^v	2.71 (3)	O2···H161^vii	3.80 (4)
C3···H81^viii	2.72 (3)	C15···H6	3.80 (3)
N···H192	2.73 (3)	C1···C4	3.802 (5)
H101···H92	2.73 (4)	C1···H182^ix	3.81 (4)
C11···H92	2.73 (4)	C14···O4^ii	3.806 (5)
C3···N	2.735 (4)	C7···C11	3.806 (5)
N···H181	2.74 (4)	C11···H102	3.81 (3)
C3···C6	2.738 (5)	S1···H182	3.81 (3)
H82···H192^vi	2.74 (4)	C9···O2^v	3.811 (5)
C2···C10	2.738 (5)	C18···S2	3.812 (4)
C11···C14	2.740 (5)	C9···C12	3.812 (5)
H81···H162	2.74 (4)	C17···H82^vi	3.82 (3)
C5···C13	2.742 (5)	C2···C14	3.816 (5)
C16···H12	2.74 (3)	C1···H91^i	3.82 (4)
C4···C7	2.749 (5)	C4···C8^viii	3.820 (5)
C12···C15	2.754 (5)	C6···C10	3.821 (5)
O1···H181	2.76 (3)	C1···C15^i	3.823 (6)
O1···H162^vi	2.76 (4)	C11···H6^iv	3.83 (3)
C2···S1	2.762 (3)	O5···H12	3.83 (3)
C6···H81	2.76 (3)	C9···S1	3.839 (4)
C11···N	2.776 (4)	C4···O1^vi	3.839 (4)
C3···H102	2.78 (4)	C2···C19^ix	3.840 (6)
C17···O5	2.786 (5)	C2···C18^ix	3.844 (5)
C10···S2	2.789 (4)	C5···O4^vi	3.844 (4)
C10···H17^v	2.79 (2)	C5···C15	3.844 (5)
H91···H17^v	2.80 (5)	C6···C16^viii	3.846 (6)
S1···H4	2.80 (3)	C7···C18^ix	3.850 (6)
S2···H92	2.82 (4)	N···H12	3.85 (3)
C17···O2	2.817 (4)	C1···C18^ix	3.854 (6)
C12···O4	2.827 (4)	C7···H91	3.86 (3)
H101···H15^i	2.83 (5)	C19···H81^vi	3.86 (3)
H82···H161	2.84 (5)	C14···H91^v	3.86 (4)
C4···O1	2.837 (4)	C10···H182^v	3.86 (3)
O4···H192	2.84 (3)	O2···H191^ix	3.87 (4)
H102···H91^i	2.84 (5)	C3···C15	3.875 (5)
N···H102	2.84 (4)	C4···H162	3.88 (4)
C10···C13	2.848 (5)	C4···S2	3.882 (3)
C2···C5	2.849 (5)	S2···H182^v	3.88 (3)
H92···H15^i	2.86 (5)	C14···H92^v	3.89 (4)
S1···H102	2.86 (4)	O2···H92^i	3.89 (4)
O4···H82^vi	2.86 (4)	S2···H4^vi	3.89 (3)
H4···H12	2.87 (4)	S1···H14^vii	3.89 (3)
H101···H191^ix	2.88 (6)	C9···C17	3.892 (5)
H102···H191^ix	2.89 (6)	C2···O1	3.893 (4)
S1···H181	2.89 (4)	O1···H192	3.89 (3)
O5···H192	2.89 (3)	S2···H4	3.90 (2)
S2···H192	2.90 (3)	C18···H102^xii	3.90 (4)
C3···C11	2.910 (4)	C6···O1^xiv	3.902 (5)
O2···H91^i	2.91 (3)	O2···H101	3.91 (4)
H162···H181^vi	2.92 (4)	C8···O2^xiv	3.906 (5)
H17···H192	2.93 (4)	S1···H192	3.91 (3)
C4···C12	2.928 (5)	C9···C18^v	3.910 (6)
H181···H191	2.93 (4)	S2···H191^v	3.91 (3)
C1···H15^i	2.94 (3)	C3···O4	3.911 (4)
O2···H181	2.95 (4)	C6···H15	3.91 (3)
H182···H192	2.95 (4)	O1···O4^vi	3.912 (4)
O5···H17	2.95 (3)	C1···O5^xi	3.915 (5)
H92···H17^v	2.96 (5)	S1···H6^viii	3.92 (3)
S1···S2	2.989 (1)	C18···H81^vi	3.92 (3)
H17···H181	2.99 (3)	C10···O4	3.918 (4)
C6···H161^viii	3.00 (4)	O2···H82^viii	3.92 (3)
O5···H101^x	3.00 (3)	O5···H14^iv	3.92 (3)
C4···H81^viii	3.00 (3)	C10···H92^v	3.92 (4)
C19···O5	3.005 (6)	C18···H162^vi	3.92 (4)
C9···H17^v	3.01 (3)	O2···H92	3.93 (4)
H101···H191^xi	3.01 (6)	C3···H6^viii	3.93 (3)
H102···H17	3.01 (5)	S2···H181	3.94 (4)
O2···H192^ix	3.02 (3)	S2···H102	3.94 (4)
C5···H161^viii	3.02 (4)	C4···C14	3.946 (5)
H91···H15^i	3.05 (6)	C13···O1^vi	3.946 (5)
H91···H191^xi	3.05 (6)	C2···C13	3.949 (5)
C4···H12	3.06 (3)	C1···S2	3.950 (4)
C18···O2	3.060 (5)	C5···C10	3.952 (5)
O2···H81^viii	3.07 (3)	C15···H161	3.95 (5)
C5···C12	3.072 (5)	S1···H162^vi	3.95 (4)
C12···H4	3.07 (3)	C5···C16^viii	3.955 (5)
H101···H182^ix	3.08 (5)	C3···H82	3.96 (3)
C17···H92	3.08 (4)	C8···H161^viii	3.96 (4)
O1···H4^vi	3.09 (3)	C2···H182^ix	3.96 (4)
H4···H6^viii	3.09 (4)	C15···H191^xi	3.96 (4)
C6···H12^ii	3.10 (3)	O4···H181	3.96 (4)
O4···H14^iv	3.12 (3)	C2···H161^viii	3.97 (5)
C2···O2	3.116 (4)	C2···S2	3.970 (3)
O2···H17	3.12 (3)	C2···H191^ix	3.98 (4)
C5···H161	3.13 (3)	N···H91^i	3.98 (4)
H6···H14	3.14 (4)	C4···O4	3.984 (4)
C9···N	3.136 (5)	S2···H17^v	3.98 (3)
H15···H191^xi	3.14 (5)	O5···H102^x	3.99 (4)
H4···H4^vi	3.14 (3)	C4···C16^viii	3.986 (5)
C2···H92	3.14 (4)	C11···H162	3.99 (4)
C2···C11	3.143 (4)	C13···S2	3.997 (4)
C7···C15	3.149 (5)	C10···S1	3.997 (4)
C6···C14	3.150 (5)	C5···S1	4.000 (3)
H81···H192^vi	3.15 (4)	C13···H182^xiii	4.00 (3)
C9···H15^i	3.16 (4)	C19···H15^x	4.00 (3)
H7···H15	3.16 (5)	C14···H81	4.00 (3)
O1···H6^viii	3.16 (3)	C7···S1	4.002 (4)
C13···H82	3.16 (3)	O5···H91	4.00 (4)
H4···H12^vi	3.17 (4)	S2···H14^iv	4.00 (3)
H7···H12^ii	3.17 (4)	C1···C17	4.006 (5)
C18···S1	3.169 (4)	C14···C18^xiii	4.006 (6)
C19···S2	3.170 (5)	C6···C11	4.012 (5)
S2···H17	3.17 (3)	C4···H4^vi	4.01 (2)
C3···C10	3.172 (5)	C6···H101	4.01 (4)
C10···H101	3.18 (3)	C17···H182^v	4.02 (3)
C10···O5	3.181 (4)	C4···H12^vi	4.02 (3)
S1···H81^viii	3.18 (3)	C15···S2	4.035 (4)
C6···C13	3.187 (5)	C18···O5	4.036 (5)
C8···C12	3.193 (5)	C6···H162^viii	4.04 (4)
C4···C11	3.194 (5)	C7···C12	4.040 (5)
C1···O2	3.197 (5)	S1···H12^vi	4.04 (3)
C15···H7	3.20 (3)	C8···C18^vi	4.042 (6)
H102···H192^ix	3.20 (5)	C3···C17	4.043 (5)
C2···H81^viii	3.20 (3)	C16···C16^iii	4.045 (6)
C16···H162^iii	3.21 (3)	C11···C17	4.053 (5)
C1···S1	3.209 (4)	C15···O5^ii	4.056 (5)
H161···H162^iii	3.21 (5)	C19···O1	4.061 (5)
C19···H102^xii	3.21 (4)	S1···H91^i	4.07 (3)
C14···H162	3.22 (4)	C19···O2	4.071 (5)
C12···H6^iv	3.22 (3)	C2···C8^viii	4.075 (5)
C1···N	3.218 (5)	O2···S2	4.076 (3)
C19···H101^xii	3.22 (4)	C13···O2^xiii	4.077 (4)
H91···H182^v	3.23 (5)	C7···C16^viii	4.086 (6)
C8···H181^vi	3.23 (3)	C5···O1^vi	4.087 (4)
C10···H102	3.23 (3)	O5···S1	4.093 (3)
C15···H102^v	3.23 (4)	C12···S1	4.099 (4)
H81···H181^vi	3.23 (4)	S1···H101	4.12 (4)
O5···H17^v	3.23 (3)	S2···H91	4.12 (4)
C4···H161^viii	3.24 (4)	C7···C11^ii	4.132 (5)
C4···C13	3.239 (5)	C18···O4	4.133 (5)
C2···C15	3.243 (5)	C11···O1	4.133 (4)
O5···H191	3.25 (5)	S1···H12	4.14 (4)
C3···H7	3.25 (3)	S1···H192^ix	4.14 (3)
C9···S2	3.250 (4)	C8···S1^xiv	4.139 (4)
C4···H6	3.25 (3)	C8···C19^vi	4.143 (6)
C15···H17^v	3.25 (3)	S1···H4^vi	4.14 (2)
O1···O4	3.257 (4)	C3···C14	4.148 (5)
C6···H4	3.26 (3)	C7···S2^ii	4.150 (4)
C2···H91	3.26 (3)	C4···C15	4.150 (5)
C12···H14	3.26 (3)	C15···O2^xiii	4.152 (5)
C7···C10	3.265 (5)	C9···O2	4.171 (5)
C11···H15	3.27 (4)	C7···O5^ii	4.174 (5)
S1···H17	3.27 (2)	S2···H15^iv	4.18 (4)
C3···C12	3.269 (4)	C6···S2^ii	4.192 (4)
H6···H161	3.27 (5)	C15···C17^v	4.209 (5)
H15···H17^v	3.27 (5)	C13···O4	4.210 (4)
C14···H6	3.28 (3)	C8···C11	4.222 (5)
C6···C16	3.279 (6)	C7···C8^viii	4.227 (6)
C12···H7^iv	3.28 (3)	C5···O1	4.230 (4)
C15···H92^v	3.28 (4)	C3···C16^viii	4.230 (6)
C9···H182^v	3.28 (3)	C15···O4^ii	4.241 (5)
C4···H81	3.28 (3)	C13···C18^xiii	4.253 (6)
H82···H12	3.29 (4)	C1···C5	4.263 (5)
C5···H162	3.29 (3)	C9···C13	4.269 (5)
H7···H182^ix	3.29 (4)	C2···C8	4.282 (5)
C14···H12	3.29 (3)	C10···C16	4.284 (6)
C6···H82	3.30 (3)	S1···H161^vii	4.30 (4)
C12···H161	3.30 (4)	C8···O1^xiv	4.304 (5)
C8···H12	3.31 (3)	C7···C16	4.307 (6)
N···H191	3.31 (4)	C9···C14^i	4.310 (6)
C5···H7	3.31 (3)	C5···C8^viii	4.314 (5)
C1···H191^ix	3.31 (4)	C10···C18^v	4.338 (6)
C5···C14	3.309 (5)	C4···C6^viii	4.342 (5)
C15···H92	3.31 (4)	C1···C14	4.350 (6)
C7···H102	3.31 (4)	C7···C19^ix	4.351 (6)
C13···H15	3.31 (3)	C6···C8^viii	4.353 (6)
C6···O4^ii	3.312 (4)	C5···O1^xiv	4.354 (4)
C6···H14	3.32 (3)	C6···C11^ii	4.357 (5)
C16···H6	3.32 (3)	C11···C17^v	4.359 (5)
O4···H7^iv	3.32 (3)	C4···C9	4.361 (5)
C13···H81	3.32 (3)	C14···O5^ii	4.369 (5)
O5···H15^iv	3.33 (4)	C12···O1	4.380 (4)
H14···H192^ii	3.33 (4)	C1···C12	4.387 (5)
C3···C9	3.329 (5)	C16···O1^xiii	4.391 (5)
C10···H12	3.33 (3)	C7···O2	4.391 (4)
O2···H182	3.33 (3)	C5···O2^xiv	4.398 (5)
C1···C15	3.332 (6)	C6···C9	4.398 (5)
H7···H191^xi	3.33 (3)	C3···C16	4.400 (5)
C8···O1^vi	3.332 (5)	C15···C18^xiii	4.403 (6)
C18···H101^xii	3.33 (3)	C9···C19^xi	4.404 (6)
C10···N	3.334 (4)	C16···C18^vi	4.419 (7)
O5···H7^iv	3.34 (3)	C1···C19^xi	4.434 (6)
N···H182	3.34 (3)	C8···C15	4.434 (6)
C17···H102	3.34 (4)	C10···C17	4.438 (5)
H6···H161^viii	3.34 (4)	C14···S1^xiii	4.465 (4)
C2···H6	3.34 (3)	C8···S1^vi	4.472 (4)
C10···H14	3.35 (3)	C6···S1	4.487 (4)
C14···O2^xiii	3.345 (4)	C14···S2	4.510 (4)
C2···N	3.350 (4)	C6···S1^xiv	4.570 (4)
C17···H91^i	3.35 (4)	C18···S2^i	4.602 (5)
C18···H92^i	3.35 (4)	C14···S2^ii	4.611 (4)
C2···H4	3.36 (2)	C5···S1^xiv	4.614 (3)
C18···H82^vi	3.36 (3)	C19···S2^i	4.632 (5)
C3···H101	3.36 (4)	C17···S2^i	4.640 (4)
C9···O5	3.366 (5)	C16···S1^vi	4.659 (5)
C19···O5^i	3.366 (6)	C15···S2^ii	4.667 (4)
H101—C1—H102	107 (4)	C12—C13—C16	119.4 (3)
H101—C1—C2	112 (2)	H14—C14—C15	122 (2)
H101—C1—C9	107 (2)	H14—C14—C13	117 (2)
H102—C1—C2	113 (2)	C15—C14—C13	120.7 (4)
H102—C1—C9	105 (2)	H15—C15—C14	121 (2)
C2—C1—C9	112.5 (3)	H15—C15—C10	117 (2)
C7—C2—C3	114.2 (3)	C14—C15—C10	122.5 (4)
C7—C2—C1	120.7 (3)	H162—C16—H161	111 (3)
C3—C2—C1	123.9 (3)	H162—C16—C13	104 (2)
C4—C3—C2	122.2 (3)	H162—C16—C8	112 (2)
C4—C3—S1	116.6 (2)	H161—C16—C13	108 (3)
C2—C3—S1	121.1 (2)	H161—C16—C8	109 (3)
H4—C4—C3	122 (2)	C13—C16—C8	112.2 (3)
H4—C4—C5	118 (2)	H17—C17—N	112 (2)
C3—C4—C5	120.1 (3)	H17—C17—C18	120 (2)
C6—C5—C4	116.8 (3)	H17—C17—C19	115 (2)
C6—C5—C8	122.1 (3)	N—C17—C18	120.7 (3)
C4—C5—C8	120.0 (3)	N—C17—C19	120.1 (3)
H6—C6—C5	116 (2)	C18—C17—C19	59.0 (3)
H6—C6—C7	122 (2)	H182—C18—H181	120 (3)
C5—C6—C7	121.2 (3)	H182—C18—C19	119 (2)
H7—C7—C6	121 (2)	H182—C18—C17	112 (2)
H7—C7—C2	115 (2)	H181—C18—C19	115 (2)
C6—C7—C2	122.1 (3)	H181—C18—C17	117 (2)
H82—C8—H81	103 (3)	C19—C18—C17	60.5 (3)
H82—C8—C5	108 (2)	H191—C19—H192	121 (3)
H82—C8—C16	111 (2)	H191—C19—C18	117 (3)
H81—C8—C5	112 (2)	H191—C19—C17	109 (2)
H81—C8—C16	110 (2)	H192—C19—C18	116 (2)
C5—C8—C16	112.2 (3)	H192—C19—C17	117 (2)
H92—C9—H91	107 (3)	C18—C19—C17	60.5 (3)
H92—C9—C10	110 (2)	C17—N—S2	116.0 (2)
H92—C9—C1	106 (2)	C17—N—S1	116.1 (2)
H91—C9—C10	112 (2)	S2—N—S1	124.4 (2)
H91—C9—C1	109 (2)	O1—S1—O2	118.6 (2)
C10—C9—C1	112.4 (3)	O1—S1—N	109.8 (2)
C15—C10—C11	114.0 (3)	O1—S1—C3	108.4 (2)
C15—C10—C9	119.9 (3)	O2—S1—N	104.2 (2)
C11—C10—C9	124.2 (3)	O2—S1—C3	109.8 (1)
C12—C11—C10	122.8 (3)	N—S1—C3	105.0 (1)
C12—C11—S2	116.0 (2)	O4—S2—O5	119.0 (2)
C10—C11—S2	121.2 (2)	O4—S2—N	109.2 (1)
H12—C12—C11	117 (2)	O4—S2—C11	108.1 (2)
H12—C12—C13	123 (2)	O5—S2—N	104.5 (2)
C11—C12—C13	120.0 (3)	O5—S2—C11	108.8 (2)
C14—C13—C12	117.6 (4)	N—S2—C11	106.6 (1)
C14—C13—C16	121.5 (4)
C9—C1—C2—C3	−76.7 (4)	C10—C11—C12—C13	0.8 (5)
C9—C1—C2—C7	90.1 (4)	C10—C11—C12—H12	176 (2)
H101—C1—C2—C3	163 (3)	S2—C11—C12—C13	−177.1 (3)
H101—C1—C2—C7	−30 (3)	S2—C11—C12—H12	−2 (2)
H102—C1—C2—C3	43 (3)	C10—C11—S2—N	−60.6 (3)
H102—C1—C2—C7	−151 (3)	C10—C11—S2—O4	−177.9 (3)
C2—C1—C9—C10	−5.3 (4)	C10—C11—S2—O5	51.6 (3)
C2—C1—C9—H91	−130 (2)	C12—C11—S2—N	117.4 (3)
C2—C1—C9—H92	115 (2)	C12—C11—S2—O4	0.1 (3)
H101—C1—C9—C10	118 (2)	C12—C11—S2—O5	−130.4 (3)
H101—C1—C9—H91	−7 (3)	C11—C12—C13—C14	−13.2 (5)
H101—C1—C9—H92	−122 (3)	C11—C12—C13—C16	153.2 (3)
H102—C1—C9—C10	−129 (3)	H12—C12—C13—C14	172 (2)
H102—C1—C9—H91	106 (4)	H12—C12—C13—C16	−22 (2)
H102—C1—C9—H92	−9 (4)	C12—C13—C14—C15	13.3 (6)
C1—C2—C3—C4	153.4 (3)	C12—C13—C14—H14	−177 (2)
C1—C2—C3—S1	−23.7 (4)	C16—C13—C14—C15	−152.8 (4)
C7—C2—C3—C4	−14.1 (4)	C16—C13—C14—H14	17 (2)
C7—C2—C3—S1	168.8 (2)	C12—C13—C16—C8	−69.7 (5)
C1—C2—C7—C6	−153.1 (4)	C12—C13—C16—H161	170 (2)
C1—C2—C7—H7	11 (2)	C12—C13—C16—H162	52 (3)
C3—C2—C7—C6	14.9 (5)	C14—C13—C16—C8	96.1 (4)
C3—C2—C7—H7	179 (2)	C14—C13—C16—H161	−24 (3)
C2—C3—C4—C5	−0.6 (5)	C14—C13—C16—H162	−143 (3)
C2—C3—C4—H4	−172 (2)	C13—C14—C15—C10	−0.8 (6)
S1—C3—C4—C5	176.6 (2)	C13—C14—C15—H15	177 (2)
S1—C3—C4—H4	5 (2)	H14—C14—C15—C10	−170 (2)
C2—C3—S1—N	68.5 (3)	H14—C14—C15—H15	8 (3)
C2—C3—S1—O1	−174.2 (2)	C19—C17—C18—C19	0.0 (3)
C2—C3—S1—O2	−43.1 (3)	C19—C17—C18—H181	104 (2)
C4—C3—S1—N	−108.8 (3)	C19—C17—C18—H182	−112 (2)
C4—C3—S1—O1	8.6 (3)	N—C17—C18—C19	−108.9 (4)
C4—C3—S1—O2	139.7 (2)	N—C17—C18—H181	−4 (2)
C3—C4—C5—C6	15.1 (5)	N—C17—C18—H182	140 (2)
C3—C4—C5—C8	−153.2 (3)	H17—C17—C18—C19	103 (2)
H4—C4—C5—C6	−173 (2)	H17—C17—C18—H181	−152 (3)
H4—C4—C5—C8	19 (2)	H17—C17—C18—H182	−8 (3)
C4—C5—C6—C7	−14.5 (5)	C18—C17—C19—C18	−0.0 (3)
C4—C5—C6—H6	175 (2)	C18—C17—C19—H191	111 (3)
C8—C5—C6—C7	153.6 (4)	C18—C17—C19—H192	−106 (2)
C8—C5—C6—H6	−17 (2)	N—C17—C19—C18	109.9 (4)
C4—C5—C8—C16	92.2 (4)	N—C17—C19—H191	−140 (3)
C4—C5—C8—H81	−143 (2)	N—C17—C19—H192	4 (2)
C4—C5—C8—H82	−31 (2)	H17—C17—C19—C18	−111 (2)
C6—C5—C8—C16	−75.5 (4)	H17—C17—C19—H191	0 (4)
C6—C5—C8—H81	49 (2)	H17—C17—C19—H192	143 (3)
C6—C5—C8—H82	162 (2)	C18—C17—N—S1	−43.9 (4)
C5—C6—C7—C2	−0.9 (6)	C18—C17—N—S2	115.8 (3)
C5—C6—C7—H7	−164 (2)	C19—C17—N—S1	−113.5 (3)
H6—C6—C7—C2	169 (2)	C19—C17—N—S2	46.2 (4)
H6—C6—C7—H7	6 (3)	H17—C17—N—S1	106 (2)
C5—C8—C16—C13	−11.8 (5)	H17—C17—N—S2	−94 (2)
C5—C8—C16—H161	108 (3)	C17—C18—C19—C17	0.0 (2)
C5—C8—C16—H162	−129 (2)	C17—C18—C19—H191	−98 (3)
H81—C8—C16—C13	−137 (2)	C17—C18—C19—H192	108 (2)
H81—C8—C16—H161	−17 (4)	H181—C18—C19—C17	−108 (2)
H81—C8—C16—H162	106 (3)	H181—C18—C19—H191	153 (4)
H82—C8—C16—C13	109 (2)	H181—C18—C19—H192	0 (3)
H82—C8—C16—H161	−131 (4)	H182—C18—C19—C17	100 (2)
H82—C8—C16—H162	−8 (3)	H182—C18—C19—H191	2 (4)
C1—C9—C10—C11	80.0 (4)	H182—C18—C19—H192	−151 (3)
C1—C9—C10—C15	−83.0 (4)	C17—N—S1—C3	−151.0 (2)
H91—C9—C10—C11	−157 (2)	C17—N—S1—O1	92.6 (3)
H91—C9—C10—C15	40 (3)	C17—N—S1—O2	−35.5 (3)
H92—C9—C10—C11	−38 (2)	S2—N—S1—C3	51.2 (2)
H92—C9—C10—C15	159 (2)	S2—N—S1—O1	−65.2 (2)
C9—C10—C11—C12	−152.8 (3)	S2—N—S1—O2	166.7 (2)
C9—C10—C11—S2	25.1 (5)	C17—N—S2—C11	145.7 (2)
C15—C10—C11—C12	11.1 (5)	C17—N—S2—O4	−97.7 (3)
C15—C10—C11—S2	−171.1 (3)	C17—N—S2—O5	30.5 (3)
C9—C10—C15—C14	153.5 (4)	S1—N—S2—C11	−56.5 (2)
C9—C10—C15—H15	−24 (2)	S1—N—S2—O4	60.1 (2)
C11—C10—C15—C14	−11.1 (5)	S1—N—S2—O5	−171.6 (2)
C11—C10—C15—H15	171 (2)

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+3/2, y−1/2, 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) x−1, y, z; (viii) x−1/2, −y+1/2, −z+1; (ix) −x+1/2, y−1/2, z; (x) −x+1, y+1/2, −z+3/2; (xi) −x+1, y−1/2, −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

Crystal data

C22H19NS2O4	F(000) = 888
Mr = 425.5	Dx = 1.488 Mg m^−3
Orthorhombic, Pmcn	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P -2n 21	Cell parameters from 23 reflections
a = 9.915 (2) Å	θ = 40.1–45.2°
b = 12.426 (1) Å	µ = 2.81 mm^−1
c = 15.418 (2) Å	T = 293 K
V = 1899.6 (5) Å^3	Block, colourless
Z = 4	0.60 × 0.60 × 0.25 mm

Data collection

ENRAF NONIUS CAD4 diffractometer	Rint = 0
Radiation source: xray tube	θmax = 74.7°, θmin = 4.6°
Graphite monochromator	h = −12→0
θ/2θ scans	k = −15→0
2069 measured reflections	l = 0→19
2069 independent reflections	2 standard reflections every 60 min
1793 reflections with refl observed if I > 2.5 σ(I )	intensity decay: none

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	Riding
R[F^2 > 2σ(F^2)] = 0.049	1/[5.2 + 0.0051*σ(Fobs)^2 + 0.00003/σ(Fobs)]
wR(F^2) = 0.054	(Δ/σ)max = 0.077
S = 0.86	Δρmax = 0.39 e Å^−3
1793 reflections	Δρmin = −0.52 e Å^−3
185 parameters	Extinction correction: Zachariasen, Eq22 p292 "Cryst. Comp." Munksgaard 1970
12 restraints	Extinction coefficient: 7384 (230)

Special details

Refinement. Sfls

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3311 (3)	0.4714 (3)	0.9892 (2)	0.035 (2)
C2	0.3884 (3)	0.3638 (3)	0.9624 (2)	0.030 (1)
C3	0.3983 (3)	0.3286 (2)	0.8763 (2)	0.027 (1)
C4	0.3991 (3)	0.2195 (3)	0.8547 (2)	0.031 (1)
C5	0.3882 (3)	0.1424 (3)	0.9195 (2)	0.035 (2)
C6	0.4090 (3)	0.1766 (3)	1.0042 (2)	0.040 (2)
C7	0.4100 (3)	0.2850 (3)	1.0251 (2)	0.038 (2)
C8	0.3298 (4)	0.0330 (3)	0.8998 (3)	0.049 (2)
C17	0.25000	0.5885 (4)	0.7493 (4)	0.037 (2)
C18	0.25000	0.5904 (5)	0.6596 (4)	0.045 (3)
C19	0.25000	0.6887 (6)	0.6170 (5)	0.068 (4)
C20	0.25000	0.7816 (6)	0.6620 (8)	0.085 (6)
C21	0.25000	0.7803 (6)	0.7507 (8)	0.080 (5)
C22	0.25000	0.6816 (5)	0.7971 (5)	0.061 (4)
N	0.25000	0.4851 (3)	0.7956 (2)	0.029 (2)
S	0.40094 (7)	0.41988 (6)	0.78910 (4)	0.0292 (4)
O1	0.4099 (3)	0.3608 (2)	0.7100 (1)	0.043 (1)
O2	0.4977 (2)	0.5032 (2)	0.8058 (2)	0.043 (1)
H101	0.362 (3)	0.486 (3)	1.050 (1)	0.04 (1)*
H102	0.363 (3)	0.529 (2)	0.949 (2)	0.032 (9)*
H4	0.397 (4)	0.200 (3)	0.7925 (8)	0.04 (1)*
H6	0.407 (4)	0.123 (2)	1.052 (2)	0.039 (9)*
H7	0.407 (4)	0.308 (3)	1.0870 (9)	0.05 (1)*
H81	0.359 (4)	0.008 (3)	0.842 (1)	0.07 (1)*
H82	0.366 (4)	−0.019 (2)	0.943 (2)	0.06 (1)*
H22	0.25000	0.679 (5)	0.8617 (9)	0.05 (1)*
H18	0.25000	0.521 (2)	0.628 (3)	0.05 (1)*
H19	0.25000	0.691 (6)	0.5523 (9)	0.09 (2)*
H20	0.25000	0.856 (2)	0.637 (4)	0.07 (2)*
H21	0.25000	0.841 (4)	0.794 (4)	0.10 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.025 (2)	0.050 (2)	0.032 (2)	−0.003 (1)	−0.004 (1)	−0.013 (1)
C2	0.013 (1)	0.047 (2)	0.028 (1)	−0.003 (1)	−0.003 (1)	−0.004 (1)
C3	0.014 (1)	0.042 (2)	0.026 (1)	0.001 (1)	−0.000 (1)	−0.000 (1)
C4	0.019 (1)	0.044 (2)	0.029 (1)	0.004 (1)	0.003 (1)	−0.004 (1)
C5	0.021 (1)	0.041 (2)	0.043 (2)	0.007 (1)	0.005 (1)	0.003 (1)
C6	0.027 (2)	0.056 (2)	0.037 (2)	0.006 (2)	0.001 (1)	0.012 (2)
C7	0.023 (1)	0.063 (2)	0.026 (1)	0.002 (2)	−0.003 (1)	−0.000 (1)
C8	0.043 (2)	0.039 (2)	0.065 (3)	0.003 (2)	0.014 (2)	−0.002 (2)
C17	0.021 (2)	0.034 (2)	0.057 (3)	0.00000	0.00000	0.007 (2)
C18	0.032 (2)	0.051 (3)	0.053 (3)	0.00000	0.00000	0.016 (3)
C19	0.034 (3)	0.074 (5)	0.095 (6)	0.00000	0.00000	0.044 (4)
C20	0.034 (3)	0.056 (5)	0.165 (9)	0.00000	0.00000	0.044 (5)
C21	0.051 (4)	0.038 (4)	0.152 (8)	0.00000	0.00000	−0.014 (5)
C22	0.050 (3)	0.043 (3)	0.091 (5)	0.00000	0.00000	−0.016 (3)
N	0.018 (2)	0.034 (2)	0.035 (2)	0.00000	0.00000	−0.001 (2)
S	0.0203 (4)	0.0423 (4)	0.0250 (4)	0.0014 (3)	0.0034 (3)	0.0015 (3)
O1	0.047 (1)	0.055 (1)	0.027 (1)	0.012 (1)	0.007 (1)	0.000 (1)
O2	0.024 (1)	0.053 (1)	0.053 (1)	−0.009 (1)	0.002 (1)	0.006 (1)

Geometric parameters (Å, º)

C1—H101	1.00 (2)	C8—C8^i	1.583 (6)
C1—H102	1.00 (3)	C17—C22	1.372 (8)
C1—C2	1.511 (5)	C17—C18	1.383 (8)
C1—C1^i	1.608 (4)	C17—N	1.469 (6)
C2—C7	1.393 (5)	C18—H18	1.00 (4)
C2—C3	1.401 (4)	C18—C19	1.39 (1)
C3—C4	1.396 (4)	C19—H19	1.00 (2)
C3—S	1.759 (3)	C19—C20	1.35 (1)
C4—H4	0.99 (2)	C20—H20	1.00 (3)
C4—C5	1.389 (5)	C20—C21	1.37 (2)
C5—C6	1.388 (5)	C21—H21	1.00 (6)
C5—C8	1.508 (5)	C21—C22	1.42 (1)
C6—H6	1.00 (2)	C22—H22	1.00 (2)
C6—C7	1.385 (5)	N—S^i	1.705 (2)
C7—H7	1.00 (2)	N—S	1.705 (2)
C8—H81	0.99 (3)	S—O1	1.426 (2)
C8—H82	1.00 (3)	S—O2	1.435 (3)
H81···H82	1.60 (4)	O2···H22	3.40 (4)
H101···H102	1.65 (3)	H102···H20^v	3.42 (6)
C22···H21	1.98 (6)	C1···C1^vi	3.440 (4)
C21···H20	1.99 (5)	C3···S^i	3.449 (3)
C20···H19	2.03 (4)	C6···C7^i	3.453 (5)
C2···H101	2.05 (3)	C1···H7^i	3.46 (3)
C2···H7	2.05 (2)	C8···H4^i	3.48 (3)
C5···H82	2.05 (3)	C6···H18^vii	3.48 (4)
C3···H4	2.05 (3)	C18···H6^ii	3.49 (3)
C7···H6	2.06 (3)	C18···H6^xii	3.49 (3)
C17···H18	2.06 (5)	H7···H22^xiii	3.49 (4)
C17···H22	2.07 (3)	C6···H19^ix	3.496 (6)
C5···H6	2.07 (2)	C3···H101^vi	3.51 (3)
C6···H7	2.07 (3)	C18···O2	3.505 (5)
C18···H19	2.07 (5)	C18···O2^i	3.505 (5)
C5···H81	2.08 (4)	C8···H6^i	3.51 (3)
C2···H102	2.08 (2)	C3···H20^ix	3.510 (5)
C5···H4	2.09 (2)	C5···H4^i	3.51 (3)
C19···H18	2.10 (3)	H102···H7	3.51 (4)
C8···H81^i	2.10 (4)	H101···H7^i	3.51 (5)
C19···H20	2.10 (3)	C4···C19^ix	3.528 (3)
C21···H22	2.12 (4)	C1···C2^vi	3.533 (4)
C1···H101^i	2.13 (3)	C20···H101^xiv	3.55 (3)
C1···H102^i	2.15 (3)	C20···H101^xv	3.55 (3)
C8···H82^i	2.15 (4)	O2···H21^ix	3.56 (4)
C20···H21	2.16 (6)	H4···H81^i	3.57 (5)
H81···H81^i	2.16 (6)	O1···H82^viii	3.57 (3)
H101···H101^i	2.21 (5)	C21···O1^xvi	3.570 (4)
H102···H102^i	2.24 (5)	C21···O1^viii	3.570 (4)
H22···H21	2.26 (8)	C2···H7^i	3.57 (3)
H82···H82^i	2.30 (5)	C3···H4^i	3.57 (3)
H101···H7	2.33 (5)	C5···H82^iv	3.57 (3)
C19···C21	2.35 (1)	C4···C20^ix	3.573 (4)
H6···H7	2.36 (4)	H6···H81	3.58 (4)
C3···C7	2.360 (4)	C5···H6^i	3.58 (3)
C4···C6	2.367 (4)	C22···S	3.582 (6)
O1···H4	2.37 (3)	C22···S^i	3.582 (6)
C18···C20	2.38 (1)	C3···C20^ix	3.585 (4)
C17···C21	2.384 (8)	H4···H82	3.60 (4)
C17···C19	2.39 (1)	C19···H82^ii	3.60 (3)
C18···C22	2.403 (9)	C19···H82^xii	3.60 (3)
C3···C5	2.411 (4)	C1···O2^vi	3.601 (4)
H18···H19	2.42 (7)	S···H101^vi	3.62 (3)
C5···C7	2.416 (5)	C8···O2^xvii	3.621 (5)
H20···H21	2.42 (8)	C18···H82^ii	3.64 (3)
C2···C6	2.423 (5)	C18···H82^xii	3.64 (3)
C20···C22	2.43 (1)	C8···H18^vii	3.66 (5)
H19···H20	2.43 (7)	C5···H19^ix	3.66 (1)
O1···H6^ii	2.44 (2)	C4···H81^i	3.68 (4)
C22···N	2.442 (7)	C5···C19^ix	3.677 (4)
C2···C4	2.446 (4)	C7···H101^i	3.69 (3)
H81···H21^iii	2.46 (6)	O2···H18	3.69 (4)
O1···O2	2.464 (3)	S···H6^ii	3.69 (2)
C18···N	2.471 (7)	C21···H4^xvi	3.70 (4)
N···O2^i	2.472 (2)	C21···H4^viii	3.70 (4)
N···O2	2.472 (2)	C20···H4^xvi	3.71 (4)
H6···H82	2.47 (4)	C20···H4^viii	3.71 (4)
C1···C7	2.507 (5)	C3···C5^i	3.724 (4)
C4···C8	2.515 (5)	S···H22	3.73 (5)
C6···C8	2.527 (5)	C3···H6	3.73 (2)
H4···H81	2.54 (5)	C8···H19^vii	3.73 (6)
H102···H22	2.55 (5)	S···H20^ix	3.73 (2)
C7···H101	2.57 (3)	C4···N	3.729 (5)
C5···C8^i	2.571 (5)	C18···H21	3.73 (6)
C1···C3	2.574 (4)	C21···N	3.732 (8)
N···O1^i	2.576 (4)	C4···O2	3.736 (4)
N···O1	2.576 (4)	C19···N	3.739 (9)
C1···C2^i	2.588 (4)	C7···H4	3.74 (2)
H6···H82^iv	2.59 (5)	C21···H18	3.74 (4)
O2···H102	2.60 (3)	C4···H7	3.75 (2)
C3···O1	2.598 (3)	C17···H20	3.75 (4)
N···H22	2.62 (5)	C1···C6	3.751 (5)
C3···O2	2.619 (4)	C3···C8	3.753 (5)
N···H18	2.63 (5)	C20···O2^viii	3.753 (7)
H101···H20^v	2.63 (5)	C20···O2^xvi	3.753 (7)
O2···H101^vi	2.63 (2)	C2···C4^i	3.755 (4)
H6···H18^vii	2.64 (4)	C6···H7^i	3.76 (4)
C1···H7	2.64 (3)	C8···O1^xvii	3.756 (5)
C6···H82	2.64 (3)	C7···H6^i	3.76 (3)
C17···S^i	2.646 (4)	C7···H19^ix	3.76 (2)
C17···S	2.646 (4)	C7···C8	3.764 (5)
C4···H81	2.67 (4)	C3···H102^i	3.77 (3)
N···H102^i	2.67 (3)	C6···H82^i	3.77 (4)
N···H102	2.67 (3)	C22···H4^xvi	3.77 (3)
O2···H81^viii	2.68 (3)	C22···H4^viii	3.77 (3)
C4···S	2.688 (3)	C19···H4^xvi	3.77 (3)
C8···H6	2.71 (3)	C19···H4^viii	3.77 (3)
S···H4	2.73 (3)	C19···H22	3.77 (2)
C3···C6	2.733 (5)	C22···H19	3.78 (2)
C8···H4	2.74 (3)	C4···H19^ix	3.780 (9)
C3···N	2.737 (4)	C4···O2^xvii	3.794 (4)
H101···H102^vi	2.74 (5)	C2···C6^i	3.811 (5)
C5···C5^i	2.740 (4)	C5···C7^i	3.812 (5)
H81···H82^i	2.74 (5)	C1···C4	3.815 (5)
C18···C21	2.74 (1)	C7···O2^vi	3.816 (4)
C2···C2^i	2.745 (4)	C7···H101^vi	3.82 (3)
C17···C20	2.75 (1)	S···H21^ix	3.82 (2)
C4···C7	2.752 (4)	C7···H22^xiii	3.82 (1)
C3···H102	2.76 (2)	C17···H4^xvi	3.82 (4)
C2···S	2.764 (3)	C17···H4^viii	3.82 (4)
H101···H102^i	2.77 (4)	N···H4^i	3.83 (3)
C19···C22	2.78 (1)	N···H4	3.83 (3)
C17···O2^i	2.813 (3)	C18···H4^xvi	3.83 (4)
C17···O2	2.813 (3)	C18···H4^viii	3.83 (4)
O1···H7^ii	2.82 (3)	C21···O2^xvi	3.833 (6)
C2···C5	2.830 (5)	C21···O2^viii	3.833 (6)
S···H102	2.84 (3)	C4···C18^ix	3.838 (4)
O1···H18	2.84 (3)	S···H102^i	3.84 (3)
C4···O1	2.842 (4)	C22···H7^xviii	3.84 (3)
H4···H4^i	2.91 (5)	C22···H7^vi	3.84 (3)
C3···C3^i	2.940 (4)	C5···C18^ix	3.844 (4)
H82···H19^vii	2.95 (6)	O1···H4^i	3.85 (3)
C4···C4^i	2.956 (4)	C3···C7^i	3.860 (4)
S···S^i	2.993 (1)	C4···C6^i	3.863 (5)
C8···H21^iii	3.00 (6)	C6···C19^ix	3.866 (5)
O2···H7^vi	3.02 (3)	C8···H82^iv	3.87 (4)
O1···H81^viii	3.04 (4)	C4···H20^ix	3.87 (1)
O2···H4^viii	3.06 (3)	C5···H6^iv	3.90 (3)
H82···H18^vii	3.07 (6)	C2···O1	3.898 (4)
C6···H82^iv	3.08 (4)	C3···C19^ix	3.899 (5)
C4···H4^i	3.09 (4)	C2···H20^ix	3.90 (2)
C1···N	3.097 (5)	C1···S^i	3.902 (3)
H102···H7^vi	3.10 (5)	O2···H4	3.90 (3)
C2···H101^vi	3.11 (3)	C4···C21^ix	3.914 (6)
H82···H21^iii	3.11 (6)	C21···S^xvi	3.920 (4)
H7···H7^i	3.11 (5)	C21···S^viii	3.920 (4)
C2···H102^vi	3.12 (3)	C6···H101	3.94 (3)
H6···H6^i	3.12 (5)	C20···S^xvi	3.937 (4)
C1···H101^vi	3.15 (3)	C20···S^viii	3.937 (4)
C6···C6^i	3.153 (5)	C2···C5^i	3.941 (4)
S···H18	3.16 (4)	C1···H7^vi	3.96 (3)
C2···O2	3.163 (4)	C6···C8^iv	3.960 (5)
H101···H101^vi	3.16 (4)	C5···H18^ix	3.96 (2)
C4···C5^i	3.167 (4)	C8···C21^iii	3.97 (1)
C2···C3^i	3.168 (4)	C1···C7^vi	3.975 (5)
O1···O1^i	3.170 (4)	O1···H6^xii	3.98 (3)
H4···H7^ii	3.17 (2)	C2···S^i	3.982 (3)
C7···C7^i	3.172 (5)	C5···S	3.994 (3)
C1···H102^vi	3.18 (3)	C3···H102^vi	4.00 (3)
C5···H81^i	3.20 (4)	O2···H101	4.00 (2)
C2···H101^i	3.20 (3)	C7···S	4.007 (3)
C6···O1^vii	3.207 (4)	C3···O1^i	4.009 (4)
C17···H21	3.21 (6)	C4···S^i	4.009 (3)
C22···H102^i	3.21 (3)	C7···H82^iv	4.01 (3)
C22···H102	3.21 (3)	C18···H81^viii	4.01 (4)
H82···H82^iv	3.22 (5)	C18···H81^xvi	4.01 (4)
O2···H20^ix	3.22 (2)	C7···H82	4.01 (3)
C1···S	3.227 (3)	S···H4^i	4.02 (4)
H102···H102^vi	3.23 (4)	C6···H81^iv	4.02 (4)
C1···H20^v	3.23 (4)	C20···O1^xvi	4.030 (7)
C2···H102^i	3.24 (3)	C20···O1^viii	4.030 (7)
C5···H82^i	3.24 (4)	C1···C22	4.031 (8)
C7···H102^vi	3.25 (3)	C5···H18^vii	4.03 (4)
C5···C6^i	3.251 (5)	C3···H19^ix	4.04 (3)
C21···H19	3.25 (3)	C5···O2^xvii	4.042 (4)
C3···H7	3.26 (1)	C22···O1^viii	4.043 (4)
C3···C4^i	3.262 (4)	C22···O1^xvi	4.043 (4)
C2···C7^i	3.263 (4)	C3···C21^ix	4.044 (6)
H6···H81^iv	3.27 (5)	C3···C17	4.052 (6)
C18···S^i	3.274 (5)	C1···C17	4.055 (6)
C18···S	3.274 (5)	C3···C6^i	4.091 (5)
C4···H6	3.27 (2)	S···O2^i	4.094 (3)
C6···H4	3.28 (1)	C2···O2^vi	4.096 (4)
C22···H20	3.28 (5)	C4···C7^i	4.117 (4)
C2···N	3.282 (4)	S···H101	4.12 (2)
C4···H82	3.28 (3)	C1···C20^v	4.14 (1)
C20···H18	3.29 (3)	C4···C17^ix	4.163 (4)
C7···H102	3.29 (2)	C5···C20^ix	4.176 (6)
C6···H6^i	3.29 (4)	C4···O1^i	4.177 (4)
C22···H18	3.29 (5)	C2···C20^ix	4.192 (7)
C17···H19	3.29 (3)	C8···S^xvii	4.194 (4)
C7···H7^i	3.30 (4)	C7···C19^ix	4.195 (6)
C17···O1^i	3.298 (5)	C1···C3^vi	4.204 (4)
C17···O1	3.298 (5)	C2···C2^vi	4.206 (4)
C1···O2	3.299 (4)	S···H7^ii	4.21 (2)
C2···H6	3.30 (3)	S···H4^viii	4.21 (3)
C5···H7	3.30 (2)	C4···C22^ix	4.220 (5)
C6···H81	3.31 (3)	C20···N	4.22 (1)
C18···H22	3.31 (2)	C5···O1	4.225 (4)
S···H81^viii	3.31 (4)	C2···C8	4.262 (5)
C22···O2	3.312 (5)	C1···C5	4.266 (5)
C22···O2^i	3.312 (5)	C21···O2	4.314 (6)
C19···H21	3.31 (6)	C21···O2^i	4.314 (6)
C18···H20	3.32 (3)	C8···C18^ix	4.325 (4)
C4···C8^i	3.317 (5)	C3···C8^i	4.329 (5)
C2···H4	3.32 (2)	C1···O2^i	4.334 (4)
C3···H101	3.33 (2)	C6···C18^ix	4.354 (5)
C8···H6^iv	3.33 (3)	C8···C18^vii	4.362 (7)
C20···H22	3.33 (3)	C7···C22^xiii	4.365 (6)
C21···H81^x	3.34 (4)	C2···C19^ix	4.369 (5)
C21···H81^xi	3.34 (4)	C1···C6^i	4.375 (5)
C1···H22	3.34 (5)	C7···C8^i	4.380 (5)
H22···H19^v	3.35 (5)	C6···C18^vii	4.386 (7)
C17···H102^i	3.35 (3)	C1···C4^i	4.394 (5)
C17···H102	3.35 (3)	C8···C19^vii	4.408 (9)
C18···O1^i	3.355 (6)	C7···C20^ix	4.437 (8)
C18···O1	3.355 (6)	C6···C20^ix	4.438 (8)
C1···C3^i	3.369 (4)	C6···S	4.488 (4)
C6···C8^i	3.373 (5)	C19···S	4.520 (8)
C1···C7^i	3.374 (5)	C19···S^i	4.520 (8)
C7···O1^vii	3.378 (4)	C1···S^vi	4.535 (3)
O1···H21^ix	3.382 (5)	C6···S^vii	4.554 (3)
S···O1^i	3.394 (3)
H101—C1—H102	111 (2)	C5—C8—C8^i	112.6 (3)
H101—C1—C2	108 (2)	C22—C17—C18	121.4 (5)
H101—C1—C1^i	108 (2)	C22—C17—N	118.5 (5)
H102—C1—C2	110 (2)	C18—C17—N	120.1 (4)
H102—C1—C1^i	108 (2)	H18—C18—C17	119 (3)
C2—C1—C1^i	112.1 (3)	H18—C18—C19	122 (3)
C7—C2—C3	115.3 (3)	C17—C18—C19	119.3 (6)
C7—C2—C1	119.3 (3)	H19—C19—C20	119 (4)
C3—C2—C1	124.2 (3)	H19—C19—C18	120 (4)
C4—C3—C2	121.9 (3)	C20—C19—C18	120.7 (8)
C4—C3—S	116.4 (2)	H20—C20—C19	126 (3)
C2—C3—S	121.6 (2)	H20—C20—C21	113 (3)
H4—C4—C5	122 (2)	C19—C20—C21	120.3 (8)
H4—C4—C3	118 (2)	H21—C21—C20	131 (3)
C5—C4—C3	119.9 (3)	H21—C21—C22	108 (3)
C6—C5—C4	117.0 (3)	C20—C21—C22	121.0 (7)
C6—C5—C8	121.5 (3)	H22—C22—C17	121 (3)
C4—C5—C8	120.5 (3)	H22—C22—C21	122 (3)
H6—C6—C7	119 (1)	C17—C22—C21	117.3 (7)
H6—C6—C5	119 (1)	C17—N—S^i	112.8 (1)
C7—C6—C5	121.2 (3)	C17—N—S	112.8 (1)
H7—C7—C6	120 (2)	S^i—N—S	122.8 (2)
H7—C7—C2	118 (2)	O1—S—O2	118.9 (1)
C6—C7—C2	121.4 (3)	O1—S—N	110.4 (2)
H81—C8—H82	107 (3)	O1—S—C3	108.9 (1)
H81—C8—C5	111 (2)	O2—S—N	103.5 (2)
H81—C8—C8^i	107 (2)	O2—S—C3	109.8 (1)
H82—C8—C5	108 (2)	N—S—C3	104.4 (2)
H82—C8—C8^i	111 (2)
H101—C1—C2—C3	−163 (2)	C5—C6—C7—C2	0.9 (5)
H101—C1—C2—C7	30 (2)	C5—C6—C7—H7	168 (3)
H102—C1—C2—C3	−41 (2)	H6—C6—C7—C2	−168 (2)
H102—C1—C2—C7	151 (2)	H6—C6—C7—H7	−1 (4)
C1^i—C1—C2—C3	79.3 (4)	C22—C17—C18—C19	−0.0001 (1)
C1^i—C1—C2—C7	−87.8 (3)	C22—C17—C18—H18	180.0000
C1—C2—C3—C4	−153.8 (3)	N—C17—C18—C19	180.0000
C1—C2—C3—S	22.7 (4)	N—C17—C18—H18	−0.0001
C7—C2—C3—C4	13.8 (4)	C18—C17—C22—C21	−0.0001 (1)
C7—C2—C3—S	−169.7 (2)	C18—C17—C22—H22	180.0000
C1—C2—C7—C6	153.6 (3)	N—C17—C22—C21	180.0000
C1—C2—C7—H7	−14 (3)	N—C17—C22—H22	−0.0001 (1)
C3—C2—C7—C6	−14.6 (4)	C18—C17—N—S	72.2 (2)
C3—C2—C7—H7	178 (3)	C18—C17—N—S^i	−72.2 (2)
C2—C3—C4—C5	0.8 (4)	C22—C17—N—S	−107.8 (2)
C2—C3—C4—H4	174 (2)	C22—C17—N—S^i	107.8 (2)
S—C3—C4—C5	−175.8 (2)	C17—C18—C19—C20	−0.0001 (1)
S—C3—C4—H4	−3 (2)	C17—C18—C19—H19	180.0000
C2—C3—S—N	−61.4 (3)	H18—C18—C19—C20	180.0000
C2—C3—S—O1	−179.3 (2)	H18—C18—C19—H19	−0.0001 (3)
C2—C3—S—O2	49.0 (3)	C18—C19—C20—C21	−0.0001 (1)
C4—C3—S—N	115.3 (2)	C18—C19—C20—H20	180.0000
C4—C3—S—O1	−2.7 (3)	H19—C19—C20—C21	180.0000
C4—C3—S—O2	−134.4 (2)	H19—C19—C20—H20	−0.0001 (2)
C3—C4—C5—C6	−14.9 (4)	C19—C20—C21—C22	−0.0001 (1)
C3—C4—C5—C8	153.4 (3)	C19—C20—C21—H21	180.0000
H4—C4—C5—C6	173 (3)	H20—C20—C21—C22	180.0000
H4—C4—C5—C8	−19 (3)	H20—C20—C21—H21	−0.0001 (2)
C4—C5—C6—C7	14.2 (5)	C20—C21—C22—C17	−0.0001 (1)
C4—C5—C6—H6	−177 (2)	C20—C21—C22—H22	180.0000
C8—C5—C6—C7	−154.0 (3)	H21—C21—C22—C17	180.0000
C8—C5—C6—H6	15 (2)	H21—C21—C22—H22	−0.0001 (1)
C4—C5—C8—H81	38 (2)	C17—N—S—C3	159.9 (3)
C4—C5—C8—H82	155 (2)	C17—N—S—O1	−83.3 (3)
C4—C5—C8—C8^i	−81.5 (4)	C17—N—S—O2	45.0 (3)
C6—C5—C8—H81	−154 (2)	S^i—N—S—C3	−59.8 (3)
C6—C5—C8—H82	−37 (2)	S^i—N—S—O1	57.0 (3)
C6—C5—C8—C8^i	86.2 (4)	S^i—N—S—O2	−174.7 (2)

Symmetry codes: (i) −x+1/2, y, z; (ii) x, −y+1/2, z−1/2; (iii) x, y−1, 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, y−1/2, −z+3/2; (x) x, y+1, z; (xi) −x+1/2, y+1, z; (xii) −x+1/2, −y+1/2, z−1/2; (xiii) x+1/2, −y+1, −z+2; (xiv) x, −y+3/2, z−1/2; (xv) −x+1/2, −y+3/2, z−1/2; (xvi) x−1/2, y+1/2, −z+3/2; (xvii) −x+1, y−1/2, −z+3/2; (xviii) x−1/2, −y+1, −z+2.