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The structures of six hydrogen-bonded adducts of 4,4′-sulfonyldiphenol with heteroaromatic amines have been determined. In 4,4′-sulfonyldiphenol–pyrazine (2/1) the pyrazine molecules lie across centres of inversion. The bisphenol molecules are linked into C(8) chains parallel to [100] by means of O—H...O=S hydrogen bonds, and antiparallel pairs of these chains are cross-linked by the pyrazine molecules, via O—H...N hydrogen bonds, to form molecular ladders containing R_6^6(50) rings between the rungs of the ladders. Each ladder is interwoven with two neighbouring ladders, thus producing a continuous two-dimensional sheet. The structure of 4,4′-sulfonyldiphenol–4,4′-bipyridyl (1/1) consists of spiral C_2^2(21) chains parallel to [010] containing alternating bisphenol and bipyridyl molecules linked by O—H...N hydrogen bonds: these chains are linked by two types of C—H...O hydrogen bonds which form C(5) chains along [001] and C_2^2(10) chains along [101], thus generating two interconnected nets characterized in the one case by a chequerboard pattern of R_6^6(44) and R_6^6(52) rings, and in the other by a single type of R_6^6(46) ring. 4,4′-Sulfonyldiphenol–trans-1,2-bis(4-pyridyl)­ethene (1/1) [systematic name: 4,4′-sulfonyldiphenol–trans-4,4′-vinyl­enedipyridine (1/1)] and 4,4′-sulfonyl­diphenol–1,2-bis(4-pyridyl)ethane (1/1) [systematic name: 4,4′-sulfonyl­diphenol–trans-4,4′-ethylenedipyridine (1/1)] are isomorphous: the 1,2-bis(4-pyridyl)­ethene component exhibits orientational disorder, corresponding approximately to a 180° rotation of ca 23% of the molecules about the N...N vector; in each compound the structure is built from C_2^2(23) chains of alternating bisphenol and bis(pyridyl) molecules connected by O—H...N hydrogen bonds, running parallel to [112] and generated by translation. The [112] chains are linked by C—H...O hydrogen bonds which generate C_2^2(12) chains parallel to [101], so forming a two-dimensional net built from R_6^6(50) rings. The structure of 4,4′-sulfonyldiphenol–4,4′-trimethyl­enedipyridine (1/1) consists of C_2^2(24) chains parallel to [100] generated by translation and consisting of alternating bisphenol and bis(pyridyl) molecules linked by O—H...N hydrogen bonds. Pairs of such chains are coiled together to form double helices, and pairs of such double helices, of opposite hand, are linked together by paired C—H...O hydrogen bonds in R_2^2(10) rings to form pairs of interwoven ladders in which the C_2^2(24) chains form the uprights and the R_2^2(10) rings form the rungs, between which are R_6^6(50) rings: an R_2^2(10) ring belonging to one ladder lies at the centre of an R_6^6(50) ring belonging to the other. 4,4′-Sulfonyldiphenol–4,4′-trimethylenedipiperidine–water (2/2/1) is a salt, 2C13H27N_2^+·2C12H9O4S·H2O, containing two independent singly protonated diamine cations, two independent bisphenolate anions, and neutral water molecules. The two independent diamine cations are linked by N—H...N hydrogen bonds into C_2^2(24) chains running parallel to [001] and generated by translation, and each type of bisphenolate anion forms an independent spiral C(12) chain, also parallel to [001]. The three types of chain are linked by the water molecules: the two types of bisphenolate chain are linked by water molecules acting as double donors in O—H...O hydrogen bonds in a C_6^4(32) chain parallel to [100], thus generating a two-dimensional net built from R_8^6(56) rings; the diamine chains are linked to these nets by means of N—H...O hydrogen bonds in which the water molecules act as acceptors and further hydrogen bonds, of N—H...O and N—H...O=S types, link these two-dimensional nets into a continuous three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, 5, 6a, 6b, 6c, 6d, 7

hkl

Structure factor file (CIF format)
Contains datablock 5

hkl

Structure factor file (CIF format)
Contains datablock 9820gaus

hkl

Structure factor file (CIF format)
Contains datablock 9822gaus

hkl

Structure factor file (CIF format)
Contains datablock 9821gaus

hkl

Structure factor file (CIF format)
Contains datablock 9767new

hkl

Structure factor file (CIF format)
Contains datablock 7

CCDC references: 134761; 134762; 134763; 134764; 134765; 134766

Comment top

None in this version

Experimental top

In the full text

Refinement top

In the full text

Computing details top

Data collection: CAD4 (Enraf-Nonius, 1992) for (5), (6a), (6b), (6c), (7); KappaCCD (Enraf-Nonius, 1997) for (6d). Cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992) for (5), (6a), (6b), (6c), (7); DENZO (Enraf-Nonius, 1997) for (6d). Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for (5), (6a), (6b), (6c), (7); DENZO (Enraf-Nonius, 1997) for (6d). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a) for (5), (6b), (6c), (6d); SHELXS97 (Sheldrick, 1997) for (6a), (7). Program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b) for (5), (6b), (6c); NRCVAX96 and SHELXL97 (Sheldrick, 1997) for (6a), (7); NRCVAX96 (Gabe et al., 1989) and SHELXL97 (Sheldrick, 1997b) for (6d). For all compounds, molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998). Software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997) for (5), (6a), (7); NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998) for (6b), (6c), (6d).

Figures top
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[Figure 17]
[Figure 18]
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[Figure 20]
[Figure 21]
In the full text
(5) 4,4'-Sulfonyldiphenol-pyrazine (2/1). top
Crystal data top
2(C12H10O4S)·C4H4N2F(000) = 604
Mr = 580.64? #Insert any comments here.
Monoclinic, P21/aDx = 1.424 Mg m3
Hall symbol: -P 2yabMo Kα radiation, λ = 0.7107 Å
a = 8.3506 (9) ÅCell parameters from 25 reflections
b = 18.0102 (17) Åθ = 9.5–20.4°
c = 9.6360 (14) ŵ = 0.25 mm1
β = 110.869 (8)°T = 294 K
V = 1354.1 (3) Å3Plate, colourless
Z = 20.42 × 0.35 × 0.25 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2431 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.008
Graphite monochromatorθmax = 27.4°, θmin = 2.3°
θ/2θ scansh = 1010
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
k = 023
Tmin = 0.915, Tmax = 0.951l = 012
3271 measured reflections3 standard reflections every 240 min
3102 independent reflections intensity decay: no decay, variation 1.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.04Calculated w = 1/[σ2(Fo2) + (0.0514P)2 + 0.2603P]
where P = (Fo2 + 2Fc2)/3
3102 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
2(C12H10O4S)·C4H4N2V = 1354.1 (3) Å3
Mr = 580.64Z = 2
Monoclinic, P21/aMo Kα radiation
a = 8.3506 (9) ŵ = 0.25 mm1
b = 18.0102 (17) ÅT = 294 K
c = 9.6360 (14) Å0.42 × 0.35 × 0.25 mm
β = 110.869 (8)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2431 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
Rint = 0.008
Tmin = 0.915, Tmax = 0.9513 standard reflections every 240 min
3271 measured reflections intensity decay: no decay, variation 1.0%
3102 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.04Δρmax = 0.25 e Å3
3102 reflectionsΔρmin = 0.22 e Å3
183 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Data from SHELXL "MPLA" calculations:

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.6443 (68) x + 11.1282 (149) y + 7.3869 (61) z = 10.2386 (143)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

7.7294 (26) x + 6.2158 (100) y - 1.7785 (58) z = 8.3599 (92)

Angle to previous plane (with approximate e.s.d.) = 84.89 (6)

* 0.0173 (0.0013) C11 * 0.0230 (0.0013) C12 * 0.0168 (0.0014) C13 * -0.0075 (0.0015) C14 * 0.0147 (0.0014) C15 * 0.0217 (0.0014) C16 * -0.0475 (0.0008) S1 * -0.0386 (0.0012) O14

Rms deviation of fitted atoms = 0.0265

- 3.6443 (68) x + 11.1282 (149) y + 7.3869 (61) z = 10.2386 (143)

Angle to previous plane (with approximate e.s.d.) = 84.89 (6)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

0.7837 (30) x + 11.9096 (88) y - 7.0233 (46) z = 10.1779 (81)

Angle to previous plane (with approximate e.s.d.) = 83.16 (5)

* 0.0168 (0.0012) C21 * 0.0203 (0.0011) C22 * 0.0202 (0.0012) C23 * -0.0041 (0.0013) C24 * 0.0146 (0.0013) C25 * 0.0282 (0.0013) C26 * -0.0513 (0.0008) S1 * -0.0448 (0.0010) O24

Rms deviation of fitted atoms = 0.0291

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.36932 (5)0.92714 (2)0.17153 (5)0.04010 (13)
O110.38809 (15)0.99950 (6)0.23802 (15)0.0559 (3)
O120.43825 (16)0.91427 (8)0.05627 (15)0.0584 (4)
O140.6544 (2)0.71281 (7)0.65639 (14)0.0660 (4)
O240.35317 (14)0.83936 (7)0.05886 (14)0.0514 (3)
C110.46227 (18)0.86282 (8)0.31429 (17)0.0364 (3)
C120.4813 (2)0.88156 (9)0.45905 (18)0.0429 (4)
C130.5472 (2)0.83100 (9)0.5723 (2)0.0478 (4)
C140.5934 (2)0.76059 (9)0.54101 (19)0.0453 (4)
C150.5778 (2)0.74230 (9)0.3968 (2)0.0519 (4)
C160.5119 (2)0.79304 (9)0.28341 (19)0.0474 (4)
C210.15116 (18)0.90416 (8)0.09853 (16)0.0341 (3)
C220.03652 (19)0.94115 (9)0.14798 (17)0.0381 (3)
C230.13372 (19)0.92083 (9)0.09453 (17)0.0393 (3)
C240.18836 (19)0.86301 (9)0.00616 (16)0.0376 (3)
C250.0738 (2)0.82674 (9)0.05755 (19)0.0435 (4)
C260.0959 (2)0.84748 (9)0.00537 (18)0.0425 (4)
N10.5778 (2)0.56714 (8)0.55556 (18)0.0539 (4)
C20.4100 (2)0.56163 (10)0.4824 (2)0.0560 (5)
C60.6667 (2)0.50485 (11)0.5726 (2)0.0539 (5)
H140.64630.67020.62480.099*
H240.40940.86340.02010.077*
H120.44920.92860.47960.051*
H130.56070.84390.66930.057*
H150.61200.69570.37660.062*
H160.50070.78060.18670.057*
H220.07400.97940.21680.046*
H230.21190.94590.12610.047*
H250.11150.78870.12680.052*
H260.17340.82360.03960.051*
H20.34260.60410.46790.067*
H60.78450.50620.62320.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02949 (19)0.0406 (2)0.0475 (2)0.00094 (15)0.01038 (16)0.00472 (17)
O110.0439 (7)0.0367 (6)0.0724 (8)0.0039 (5)0.0028 (6)0.0021 (6)
O120.0420 (6)0.0789 (9)0.0612 (8)0.0045 (6)0.0268 (6)0.0168 (7)
O140.0895 (11)0.0456 (7)0.0473 (7)0.0030 (7)0.0052 (7)0.0045 (6)
O240.0338 (6)0.0634 (8)0.0546 (7)0.0094 (5)0.0130 (5)0.0065 (6)
C110.0284 (7)0.0367 (7)0.0400 (8)0.0014 (6)0.0070 (6)0.0016 (6)
C120.0416 (8)0.0375 (8)0.0464 (9)0.0020 (6)0.0118 (7)0.0082 (7)
C130.0542 (10)0.0463 (9)0.0380 (8)0.0003 (8)0.0106 (7)0.0072 (7)
C140.0447 (9)0.0392 (8)0.0424 (9)0.0012 (7)0.0039 (7)0.0003 (7)
C150.0619 (11)0.0374 (8)0.0504 (10)0.0115 (8)0.0125 (8)0.0058 (7)
C160.0534 (10)0.0452 (9)0.0395 (8)0.0075 (7)0.0113 (7)0.0070 (7)
C210.0286 (7)0.0366 (7)0.0347 (7)0.0013 (6)0.0084 (6)0.0021 (6)
C220.0368 (8)0.0414 (8)0.0340 (7)0.0005 (6)0.0102 (6)0.0050 (6)
C230.0340 (7)0.0494 (9)0.0351 (8)0.0051 (6)0.0131 (6)0.0008 (7)
C240.0321 (7)0.0440 (8)0.0334 (7)0.0013 (6)0.0076 (6)0.0059 (6)
C250.0413 (8)0.0428 (8)0.0429 (9)0.0023 (7)0.0105 (7)0.0103 (7)
C260.0370 (8)0.0466 (9)0.0449 (9)0.0054 (6)0.0158 (7)0.0052 (7)
N10.0510 (9)0.0475 (8)0.0582 (9)0.0007 (7)0.0133 (7)0.0091 (7)
C20.0482 (10)0.0464 (10)0.0712 (12)0.0123 (8)0.0188 (9)0.0132 (9)
C60.0381 (8)0.0579 (10)0.0601 (11)0.0045 (8)0.0106 (8)0.0193 (9)
Geometric parameters (Å, º) top
S1—O111.4360 (13)C15—C161.380 (2)
S1—O121.4401 (13)C21—C221.383 (2)
S1—C211.7527 (15)C21—C261.389 (2)
S1—C111.7539 (15)C22—C231.378 (2)
O14—C141.354 (2)C23—C241.385 (2)
O24—C241.3548 (18)C24—C251.387 (2)
C11—C161.388 (2)C25—C261.376 (2)
C11—C121.388 (2)N1—C61.323 (2)
C12—C131.377 (2)N1—C21.329 (2)
C13—C141.390 (2)C2—C6i1.372 (3)
C14—C151.388 (2)C6—C2i1.372 (3)
O11—S1—O12118.69 (8)C15—C16—C11119.69 (15)
O11—S1—C21109.03 (7)C22—C21—C26120.64 (14)
O12—S1—C21107.24 (8)C22—C21—S1119.74 (12)
O11—S1—C11107.58 (7)C26—C21—S1119.59 (11)
O12—S1—C11108.17 (8)C23—C22—C21119.47 (14)
C21—S1—C11105.37 (7)C22—C23—C24120.00 (14)
C16—C11—C12119.97 (15)O24—C24—C23122.41 (14)
C16—C11—S1120.81 (12)O24—C24—C25117.12 (14)
C12—C11—S1119.19 (12)C23—C24—C25120.47 (14)
C13—C12—C11120.41 (15)C26—C25—C24119.55 (15)
C12—C13—C14119.65 (16)C25—C26—C21119.83 (14)
O14—C14—C15123.03 (15)C6—N1—C2116.18 (16)
O14—C14—C13116.99 (16)N1—C2—C6i121.92 (16)
C15—C14—C13119.98 (16)N1—C6—C2i121.91 (17)
C16—C15—C14120.27 (15)
O11—S1—C11—C16159.94 (13)O12—S1—C21—C22149.18 (13)
O12—S1—C11—C1630.60 (16)C11—S1—C21—C2295.74 (13)
C21—S1—C11—C1683.84 (15)O11—S1—C21—C26162.34 (13)
O11—S1—C11—C1222.02 (15)O12—S1—C21—C2632.65 (15)
O12—S1—C11—C12151.36 (13)C11—S1—C21—C2682.43 (14)
C21—S1—C11—C1294.21 (14)C26—C21—C22—C230.7 (2)
C16—C11—C12—C130.8 (2)S1—C21—C22—C23177.44 (12)
S1—C11—C12—C13177.27 (13)C21—C22—C23—C241.0 (2)
C11—C12—C13—C140.6 (3)C22—C23—C24—O24178.02 (14)
C12—C13—C14—O14178.76 (16)C22—C23—C24—C252.1 (2)
C12—C13—C14—C151.9 (3)O24—C24—C25—C26178.68 (15)
O14—C14—C15—C16178.83 (17)C23—C24—C25—C261.4 (2)
C13—C14—C15—C161.9 (3)C24—C25—C26—C210.3 (3)
C14—C15—C16—C110.5 (3)C22—C21—C26—C251.4 (2)
C12—C11—C16—C150.8 (3)S1—C21—C26—C25176.78 (13)
S1—C11—C16—C15177.21 (14)C6—N1—C2—C6i0.1 (3)
O11—S1—C21—C2219.49 (15)C2—N1—C6—C2i0.1 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N10.821.992.792 (2)167
O24—H24···O12ii0.821.912.732 (2)174
C6—H6···O11iii0.932.583.511 (2)176
C12—H12···O110.932.542.911 (2)104
C13—H13···O24iv0.932.463.353 (2)161
C22—H22···O110.932.582.943 (2)104
Symmetry codes: (ii) x1, y, z; (iii) x+3/2, y1/2, z+1; (iv) x+1, y, z+1.
(6a) 4,4'-Sulfonyldiphenol-4,4'-bipyridyl (1/1) top
Crystal data top
C12H10O4S·C10H8N2F(000) = 848
Mr = 406.44? #Insert any comments here.
Monoclinic, P21/nDx = 1.380 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.7107 Å
a = 7.5765 (10) ÅCell parameters from 25 reflections
b = 23.9154 (10) Åθ = 9.5–18.8°
c = 11.225 (2) ŵ = 0.20 mm1
β = 105.921 (10)°T = 294 K
V = 1955.9 (4) Å3Needle, colourless
Z = 40.42 × 0.22 × 0.18 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2461 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.011
Graphite monochromatorθmax = 25.1°, θmin = 2.1°
θ/2θ scansh = 98
Absorption correction: gaussian
ABSO in NRCVAX96 (Gabe et al., 1989)
k = 028
Tmin = 0.952, Tmax = 0.971l = 013
3774 measured reflections3 standard reflections every 120 min
3504 independent reflections intensity decay: no decay, variation 0.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.098Calculated w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0855P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3504 reflectionsΔρmax = 0.23 e Å3
265 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (9)
Crystal data top
C12H10O4S·C10H8N2V = 1955.9 (4) Å3
Mr = 406.44Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5765 (10) ŵ = 0.20 mm1
b = 23.9154 (10) ÅT = 294 K
c = 11.225 (2) Å0.42 × 0.22 × 0.18 mm
β = 105.921 (10)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2461 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSO in NRCVAX96 (Gabe et al., 1989)
Rint = 0.011
Tmin = 0.952, Tmax = 0.9713 standard reflections every 120 min
3774 measured reflections intensity decay: no decay, variation 0.6%
3504 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.05Δρmax = 0.23 e Å3
3504 reflectionsΔρmin = 0.25 e Å3
265 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean plane details ex last SHELXL97 run

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.3860 (0.0019) x + 3.7745 (0.0288) y - 4.7001 (0.0081) z = 3.0802 (0.0047)

* 0.0127 (0.0019) N31 * -0.0068 (0.0021) C32 * -0.0049 (0.0021) C33 * -0.0012 (0.0020) C34 * -0.0170 (0.0022) C35 * 0.0056 (0.0020) C36 * 0.0115 (0.0014) C44

Rms deviation of fitted atoms = 0.0099

6.9788 (0.0031) x - 5.5098 (0.0246) y - 6.2238 (0.0060) z = 2.2149 (0.0066)

Angle to previous plane (with approximate e.s.d.) = 24.36 (6)

* -0.0033 (0.0017) N41 * 0.0018 (0.0017) C42 * 0.0021 (0.0019) C43 * -0.0044 (0.0019) C44 * 0.0029 (0.0018) C45 * 0.0009 (0.0017) C46 * 0.0001 (0.0013) C34

Rms deviation of fitted atoms = 0.0026

5.6319 (0.0068) x + 3.9321 (0.0244) y + 4.7102 (0.0140) z = 3.5619 (0.0071)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

1.1941 (0.0055) x + 20.0164 (0.0072) y - 6.1423 (0.0047) z = 5.9051 (0.0040)

Angle to previous plane (with approximate e.s.d.) = 85.12 (7)

* 0.0694 (0.0017) C21 * 0.0508 (0.0016) C22 * 0.0173 (0.0017) C23 * -0.0149 (0.0018) C24 * 0.0144 (0.0017) C25 * 0.0551 (0.0016) C26 * -0.1181 (0.0010) S1 * -0.0739 (0.0013) O24

Rms deviation of fitted atoms = 0.0618

5.6319 (0.0068) x + 3.9321 (0.0244) y + 4.7102 (0.0140) z = 3.5619 (0.0071)

Angle to previous plane (with approximate e.s.d.) = 85.12 (7)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

7.0510 (0.0028) x - 6.4997 (0.0108) y - 5.5105 (0.0083) z = 2.1951 (0.0031)

Angle to previous plane (with approximate e.s.d.) = 60.78 (7)

* 0.0056 (0.0017) C11 * 0.0050 (0.0017) C12 * -0.0033 (0.0018) C13 * -0.0048 (0.0019) C14 * 0.0056 (0.0017) C15 * -0.0038 (0.0016) C16 * -0.0043 (0.0010) S1 * 0.0001 (0.0014) O14

Rms deviation of fitted atoms = 0.0044

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.50024 (8)0.24501 (2)0.04646 (5)0.03750 (17)
O110.6892 (2)0.26237 (6)0.02331 (14)0.0484 (4)
O120.3867 (2)0.24369 (6)0.17218 (13)0.0478 (4)
O140.4628 (3)0.02237 (6)0.16747 (14)0.0576 (5)
O240.1492 (2)0.36777 (8)0.27812 (14)0.0578 (5)
C110.4917 (3)0.17847 (8)0.01930 (17)0.0344 (5)
C120.5800 (3)0.16908 (9)0.14344 (18)0.0424 (5)
C130.5713 (3)0.11760 (9)0.19461 (19)0.0441 (6)
C140.4748 (3)0.07416 (8)0.12264 (18)0.0388 (5)
C150.3884 (3)0.08386 (9)0.00124 (19)0.0432 (5)
C160.3947 (3)0.13566 (8)0.05259 (18)0.0380 (5)
C210.3963 (3)0.28776 (8)0.04213 (18)0.0369 (5)
C220.5046 (3)0.31290 (9)0.14813 (19)0.0412 (5)
C230.4241 (3)0.34028 (9)0.2271 (2)0.0451 (6)
C240.2343 (3)0.34222 (9)0.20179 (19)0.0418 (5)
C250.1260 (3)0.31734 (9)0.0949 (2)0.0468 (6)
C260.2065 (3)0.29020 (9)0.0155 (2)0.0429 (5)
N310.6742 (3)0.00330 (8)0.39881 (17)0.0543 (5)
C320.7099 (4)0.05730 (10)0.4157 (2)0.0626 (7)
C330.7944 (4)0.08108 (10)0.5289 (2)0.0574 (7)
C340.8442 (3)0.04787 (8)0.63313 (19)0.0411 (5)
C350.8023 (4)0.00828 (9)0.6157 (2)0.0584 (7)
C360.7209 (4)0.02832 (10)0.4990 (2)0.0626 (7)
N411.1158 (3)0.11110 (8)0.99419 (17)0.0502 (5)
C421.1305 (3)0.05829 (10)0.9630 (2)0.0507 (6)
C431.0455 (3)0.03670 (9)0.8486 (2)0.0506 (6)
C440.9369 (3)0.07054 (8)0.75781 (19)0.0393 (5)
C450.9223 (3)0.12621 (9)0.7896 (2)0.0487 (6)
C461.0126 (3)0.14408 (10)0.9069 (2)0.0537 (6)
H140.53140.02000.23790.086*
H240.22350.37360.34530.087*
H120.64510.19780.19190.051*
H130.63020.11150.27790.053*
H150.32540.05490.05020.052*
H160.33400.14200.13550.046*
H220.63190.31130.16580.049*
H230.49690.35760.29780.054*
H250.00120.31910.07710.056*
H260.13380.27350.05600.052*
H320.67600.08070.34700.075*
H330.81760.11930.53490.069*
H350.82930.03250.68310.070*
H360.69710.06650.48990.075*
H421.20260.03451.02220.061*
H431.06100.00080.83200.061*
H450.85230.15110.73210.058*
H461.00080.18140.92650.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0405 (3)0.0362 (3)0.0330 (3)0.0015 (2)0.0054 (2)0.0021 (2)
O110.0417 (9)0.0518 (9)0.0530 (9)0.0064 (7)0.0155 (7)0.0002 (7)
O120.0571 (10)0.0469 (9)0.0329 (8)0.0058 (8)0.0013 (7)0.0034 (6)
O140.0734 (13)0.0406 (9)0.0481 (10)0.0083 (8)0.0015 (9)0.0071 (7)
O240.0477 (11)0.0752 (11)0.0498 (10)0.0038 (9)0.0123 (8)0.0154 (9)
C110.0324 (12)0.0349 (10)0.0327 (11)0.0047 (9)0.0037 (9)0.0011 (8)
C120.0481 (14)0.0386 (12)0.0326 (11)0.0012 (10)0.0021 (10)0.0041 (9)
C130.0524 (15)0.0428 (12)0.0299 (11)0.0039 (11)0.0009 (10)0.0022 (9)
C140.0417 (13)0.0360 (11)0.0361 (11)0.0018 (10)0.0059 (10)0.0032 (9)
C150.0430 (14)0.0404 (12)0.0396 (12)0.0064 (10)0.0000 (10)0.0031 (9)
C160.0359 (12)0.0437 (12)0.0293 (10)0.0000 (10)0.0001 (9)0.0006 (9)
C210.0380 (13)0.0324 (11)0.0362 (11)0.0008 (9)0.0034 (9)0.0012 (8)
C220.0334 (12)0.0433 (12)0.0429 (12)0.0002 (10)0.0036 (10)0.0033 (10)
C230.0396 (14)0.0482 (13)0.0420 (12)0.0047 (11)0.0019 (10)0.0120 (10)
C240.0454 (15)0.0382 (12)0.0411 (12)0.0025 (10)0.0110 (10)0.0012 (9)
C250.0326 (13)0.0533 (14)0.0499 (14)0.0028 (11)0.0036 (11)0.0046 (11)
C260.0390 (13)0.0420 (12)0.0408 (12)0.0012 (10)0.0008 (10)0.0064 (10)
N310.0608 (14)0.0507 (12)0.0445 (11)0.0019 (10)0.0030 (10)0.0062 (9)
C320.083 (2)0.0516 (15)0.0423 (14)0.0033 (14)0.0004 (14)0.0060 (11)
C330.0735 (19)0.0397 (13)0.0501 (14)0.0057 (12)0.0019 (13)0.0033 (10)
C340.0373 (13)0.0402 (12)0.0430 (12)0.0004 (10)0.0066 (10)0.0017 (9)
C350.0802 (19)0.0402 (13)0.0458 (13)0.0058 (13)0.0020 (13)0.0015 (10)
C360.083 (2)0.0421 (13)0.0532 (15)0.0066 (13)0.0017 (14)0.0080 (11)
N410.0454 (12)0.0589 (12)0.0458 (11)0.0037 (10)0.0116 (10)0.0107 (10)
C420.0501 (15)0.0551 (15)0.0424 (13)0.0004 (12)0.0048 (11)0.0032 (11)
C430.0524 (15)0.0416 (12)0.0503 (13)0.0017 (11)0.0016 (12)0.0024 (11)
C440.0358 (12)0.0410 (12)0.0401 (12)0.0032 (10)0.0087 (10)0.0017 (9)
C450.0496 (15)0.0439 (12)0.0483 (13)0.0031 (11)0.0062 (11)0.0002 (10)
C460.0590 (17)0.0453 (13)0.0546 (15)0.0038 (12)0.0117 (13)0.0126 (11)
Geometric parameters (Å, º) top
S1—O111.4438 (15)C24—C251.388 (3)
S1—O121.4377 (15)C25—C261.373 (3)
S1—C111.7628 (19)N31—C321.322 (3)
S1—C211.756 (2)N31—C361.320 (3)
O14—C141.349 (2)C32—C331.379 (3)
O24—C241.351 (3)C33—C341.378 (3)
C11—C121.389 (3)C34—C351.381 (3)
C11—C161.384 (3)C34—C441.485 (3)
C12—C131.368 (3)C35—C361.372 (3)
C13—C141.394 (3)N41—C421.323 (3)
C14—C151.384 (3)N41—C461.332 (3)
C15—C161.373 (3)C42—C431.370 (3)
C21—C221.384 (3)C43—C441.383 (3)
C21—C261.388 (3)C44—C451.391 (3)
C22—C231.373 (3)C45—C461.375 (3)
C23—C241.388 (3)
O11—S1—O12118.68 (10)O24—C24—C25118.1 (2)
O12—S1—C21109.15 (9)O24—C24—C23122.2 (2)
O11—S1—C21107.89 (10)C23—C24—C25119.8 (2)
O12—S1—C11108.08 (9)C24—C25—C26120.1 (2)
O11—S1—C11109.42 (9)C21—C26—C25119.9 (2)
C11—S1—C21102.40 (9)C32—N31—C36116.2 (2)
C12—C11—C16119.87 (18)N31—C32—C33124.1 (2)
S1—C11—C16119.90 (15)C32—C33—C34119.6 (2)
S1—C11—C12120.23 (15)C33—C34—C35116.2 (2)
C11—C12—C13120.12 (19)C33—C34—C44122.55 (19)
C12—C13—C14120.36 (19)C35—C34—C44121.3 (2)
O14—C14—C15117.83 (18)C34—C35—C36120.0 (2)
O14—C14—C13123.12 (18)N31—C36—C35123.9 (2)
C13—C14—C15119.05 (19)C42—N41—C46116.5 (2)
C14—C15—C16120.79 (19)N41—C42—C43123.7 (2)
C11—C16—C15119.80 (18)C42—C43—C44120.2 (2)
C22—C21—C26120.2 (2)C43—C44—C45116.4 (2)
S1—C21—C22119.17 (17)C34—C44—C43120.87 (19)
S1—C21—C26120.11 (16)C34—C44—C45122.75 (19)
C21—C22—C23119.9 (2)C44—C45—C46119.3 (2)
C22—C23—C24120.2 (2)N41—C46—C45123.9 (2)
O12—S1—C11—C163.4 (2)C22—C23—C24—C251.3 (3)
O11—S1—C11—C16127.14 (18)O24—C24—C25—C26179.1 (2)
C21—S1—C11—C16118.59 (18)C23—C24—C25—C261.0 (3)
O12—S1—C11—C12175.72 (17)C24—C25—C26—C210.1 (3)
O11—S1—C11—C1253.7 (2)C22—C21—C26—C250.4 (3)
C21—S1—C11—C1260.6 (2)S1—C21—C26—C25170.95 (17)
C16—C11—C12—C130.1 (3)C36—N31—C32—C331.4 (4)
S1—C11—C12—C13179.23 (18)N31—C32—C33—C340.9 (4)
C11—C12—C13—C140.3 (4)C32—C33—C34—C350.8 (4)
C12—C13—C14—O14179.3 (2)C32—C33—C34—C44179.5 (2)
C12—C13—C14—C150.2 (3)C33—C34—C35—C362.0 (4)
O14—C14—C15—C16179.8 (2)C44—C34—C35—C36178.4 (2)
C13—C14—C15—C161.0 (3)C32—N31—C36—C350.2 (4)
C14—C15—C16—C111.4 (3)C34—C35—C36—N311.6 (4)
C12—C11—C16—C150.9 (3)C46—N41—C42—C430.4 (4)
S1—C11—C16—C15179.92 (17)N41—C42—C43—C440.1 (4)
O12—S1—C21—C22155.04 (16)C42—C43—C44—C450.6 (3)
O11—S1—C21—C2224.81 (19)C42—C43—C44—C34179.8 (2)
C11—S1—C21—C2290.58 (18)C33—C34—C44—C43155.1 (2)
O12—S1—C21—C2633.5 (2)C35—C34—C44—C4325.2 (3)
O11—S1—C21—C26163.77 (17)C33—C34—C44—C4524.0 (4)
C11—S1—C21—C2680.83 (18)C35—C34—C44—C45155.6 (2)
C26—C21—C22—C230.0 (3)C43—C44—C45—C460.7 (3)
S1—C21—C22—C23171.37 (16)C34—C44—C45—C46179.9 (2)
C21—C22—C23—C240.8 (3)C42—N41—C46—C450.4 (4)
C22—C23—C24—O24178.7 (2)C44—C45—C46—N410.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N310.821.922.721 (3)167
O24—H24···N41i0.821.912.731 (3)176
C12—H12···O12ii0.932.473.376 (3)165
C42—H42···O14iii0.932.583.487 (3)167
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z+1.
(6b) 4,4'-Sulfonyldiphenol - trans-1,2-bis(4-pyridyl)ethylene (1/1) top
Crystal data top
C12H10O4S·C12H10N2F(000) = 452
Mr = 432.48? #Insert any comments here.
Triclinic, P1Dx = 1.347 Mg m3
a = 7.3981 (8) ÅMo Kα radiation, λ = 0.7107 Å
b = 12.7472 (15) ÅCell parameters from 25 reflections
c = 13.0006 (13) Åθ = 9.9–18.2°
α = 115.037 (8)°µ = 0.19 mm1
β = 102.398 (10)°T = 294 K
γ = 94.239 (10)°Needle, colourless
V = 1065.9 (2) Å30.42 × 0.28 × 0.24 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
2948 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.000
Graphite monochromatorθmax = 25.2°, θmin = 2.9°
θ/2θ scansh = 88
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
k = 015
Tmin = 0.949, Tmax = 0.967l = 1514
3829 measured reflections3 standard reflections every 120 min
3829 independent reflections intensity decay: no decay, variation 1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.100Calculated w = 1/[σ2(Fo2) + (0.0529P)2 + 0.2472P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
3829 reflectionsΔρmax = 0.21 e Å3
330 parametersΔρmin = 0.20 e Å3
41 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0143 (18)
Crystal data top
C12H10O4S·C12H10N2γ = 94.239 (10)°
Mr = 432.48V = 1065.9 (2) Å3
Triclinic, P1Z = 2
a = 7.3981 (8) ÅMo Kα radiation
b = 12.7472 (15) ŵ = 0.19 mm1
c = 13.0006 (13) ÅT = 294 K
α = 115.037 (8)°0.42 × 0.28 × 0.24 mm
β = 102.398 (10)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2948 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
Rint = 0.000
Tmin = 0.949, Tmax = 0.9673 standard reflections every 120 min
3829 measured reflections intensity decay: no decay, variation 1.0%
3829 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03641 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.98Δρmax = 0.21 e Å3
3829 reflectionsΔρmin = 0.20 e Å3
330 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean-plane calculations ex the final SHELXL run. The symmetry transformations are defined by:- $1 = -x, -y, -z $2 = 1 - x, 1 - y, 2 - z

##################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.2237 (0.0018) x - 0.1035 (0.0098) y - 5.4285 (0.0095) z = 1.7118 (0.0053)

* 0.0117 (0.0012) C11 * -0.0050 (0.0013) C12 * -0.0072 (0.0013) C13 * 0.0127 (0.0013) C14 * -0.0062 (0.0014) C15 * -0.0060 (0.0014) C16 - 3.4348 (0.0079) N41_$1 - 3.7468 (0.0062) C42_$1 - 3.8333 (0.0036) C43_$1 - 3.6297 (0.0033) C44_$1 - 3.3299 (0.0039) C45_$1 - 3.2215 (0.0048) C46_$1

Rms deviation of fitted atoms = 0.0087

##############################

- 6.8848 (0.0062) x - 2.8713 (0.0253) y + 6.7430 (0.0270) z = 1.9027 (0.0122)

Angle to previous plane (with approximate e.s.d.) = 13.52 (13)

* -0.0004 (0.0039) N41_$1 * 0.0100 (0.0040) C42_$1 * -0.0084 (0.0027) C43_$1 * -0.0021 (0.0023) C44_$1 * 0.0112 (0.0023) C45_$1 * -0.0103 (0.0027) C46_$1 - 3.7399 (0.0075) C11 - 3.4054 (0.0086) C12 - 3.1973 (0.0072) C13 - 3.3263 (0.0045) C14 - 3.6269 (0.0030) C15 - 3.8322 (0.0049) C16

Rms deviation of fitted atoms = 0.0082

##############################

7.2237 (0.0018) x - 0.1035 (0.0098) y - 5.4285 (0.0095) z = 1.7118 (0.0053)

Angle to previous plane (with approximate e.s.d.) = 13.52 (13)

* 0.0117 (0.0012) C11 * -0.0050 (0.0013) C12 * -0.0072 (0.0013) C13 * 0.0127 (0.0013) C14 * -0.0062 (0.0014) C15 * -0.0060 (0.0014) C16 - 3.5173 (0.0291) N61_$1 - 3.4051 (0.0178) C62_$1 - 3.4304 (0.0131) C63_$1 - 3.5954 (0.0104) C64_$1 - 3.7213 (0.0161) C65_$1 - 3.6652 (0.0253) C66_$1

Rms deviation of fitted atoms = 0.0087

##############################

- 7.0717 (0.0205) x - 1.4387 (0.1093) y + 6.3165 (0.1099) z = 2.0307 (0.0482)

Angle to previous plane (with approximate e.s.d.) = 7.1 (5)

* 0.0014 (0.0130) N61_$1 * 0.0042 (0.0068) C62_$1 * -0.0045 (0.0087) C63_$1 * -0.0004 (0.0104) C64_$1 * 0.0057 (0.0127) C65_$1 * -0.0064 (0.0162) C66_$1 - 3.6969 (0.0330) C11 - 3.5099 (0.0341) C12 - 3.4170 (0.0259) C13 - 3.5154 (0.0133) C14 - 3.6674 (0.0119) C15 - 3.7577 (0.0236) C16

Rms deviation of fitted atoms = 0.0044

##############################

0.7073 (0.0055) x + 12.3745 (0.0032) y - 3.9339 (0.0094) z = 4.3504 (0.0081)

Angle to previous plane (with approximate e.s.d.) = 76.6 (5)

* 0.0081 (0.0012) C21 * -0.0078 (0.0014) C22 * -0.0014 (0.0014) C23 * 0.0104 (0.0013) C24 * -0.0102 (0.0013) C25 * 0.0009 (0.0013) C26 - 3.4950 (0.0027) C21_$2 - 3.4790 (0.0027) C22_$2 - 3.4854 (0.0029) C23_$2 - 3.4972 (0.0026) C24_$2 - 3.4766 (0.0027) C25_$2 - 3.4878 (0.0027) C26_$2

Rms deviation of fitted atoms = 0.0075

##############################

0.7073 (0.0055) x + 12.3745 (0.0032) y - 3.9339 (0.0094) z = 0.8636 (0.0091)

Angle to previous plane = 0.0

* -0.0081 (0.0012) C21_$2 * 0.0078 (0.0014) C22_$2 * 0.0014 (0.0014) C23_$2 * -0.0104 (0.0013) C24_$2 * 0.0102 (0.0013) C25_$2 * -0.0009 (0.0013) C26_$2 3.4950 (0.0027) C21 3.4790 (0.0027) C22 3.4854 (0.0029) C23 3.4972 (0.0026) C24 3.4766 (0.0027) C25 3.4878 (0.0027) C26

Rms deviation of fitted atoms = 0.0075

##############################

7.2402 (0.0033) x + 0.6161 (0.0367) y - 5.3065 (0.0230) z = 1.8163 (0.0025)

Angle to previous plane (with approximate e.s.d.) = 79.41 (17)

* -0.0107 (0.0054) N31 * 0.0181 (0.0057) C32 * -0.0141 (0.0051) C33 * 0.0041 (0.0031) C34 * 0.0037 (0.0035) C35 * -0.0006 (0.0028) C36 * -0.0006 (0.0031) C37

Rms deviation of fitted atoms = 0.0098

##############################

6.9041 (0.0047) x + 2.8432 (0.0246) y - 6.6403 (0.0170) z = 1.8496 (0.0071)

Angle to previous plane (with approximate e.s.d.) = 10.48 (16)

* -0.0102 (0.0045) N41 * 0.0069 (0.0040) C42 * 0.0013 (0.0031) C43 * 0.0141 (0.0022) C44 * 0.0206 (0.0028) C45 * -0.0138 (0.0025) C46 * -0.0188 (0.0024) C47

Rms deviation of fitted atoms = 0.0138

##############################

7.3288 (0.0076) x - 0.8049 (0.1338) y - 4.3665 (0.0997) z = 1.7875 (0.0097)

Angle to previous plane (with approximate e.s.d.) = 17.1 (4)

* 0.0329 (0.0171) N51 * 0.0033 (0.0068) C52 * -0.0176 (0.0126) C53 * 0.0327 (0.0122) C54 * 0.0679 (0.0166) C55 * -0.0865 (0.0175) C56 * -0.0327 (0.0108) C57

Rms deviation of fitted atoms = 0.0473

##############################

7.0749 (0.0154) x + 1.4381 (0.1089) y - 6.2976 (0.0748) z = 2.0200 (0.0256)

Angle to previous plane (with approximate e.s.d.) = 11.4 (5)

* -0.0005 (0.0156) N61 * 0.0036 (0.0064) C62 * -0.0026 (0.0109) C63 * 0.0028 (0.0098) C64 * 0.0076 (0.0143) C65 * -0.0071 (0.0159) C66 * -0.0037 (0.0092) C67

Rms deviation of fitted atoms = 0.0046

##############################

5.2262 (0.0062) x - 7.8164 (0.0114) y + 6.1170 (0.0118) z = 4.5879 (0.0076)

Angle to previous plane (with approximate e.s.d.) = 61.7 (4)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

##############################

7.2110 (0.0017) x - 0.2498 (0.0077) y - 5.4835 (0.0093) z = 1.6533 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 55.55 (7)

* -0.0342 (0.0014) C11 * -0.0392 (0.0013) C12 * -0.0191 (0.0014) C13 * 0.0118 (0.0015) C14 * -0.0189 (0.0015) C15 * -0.0410 (0.0015) C16 * 0.0812 (0.0009) S1 * 0.0593 (0.0011) O14

Rms deviation of fitted atoms = 0.0438

##############################

5.2262 (0.0062) x - 7.8164 (0.0114) y + 6.1170 (0.0118) z = 4.5879 (0.0076)

Angle to previous plane (with approximate e.s.d.) = 55.55 (7)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

##############################

0.6479 (0.0047) x + 12.3638 (0.0032) y - 3.7663 (0.0054) z = 4.4883 (0.0061)

Angle to previous plane (with approximate e.s.d.) = 65.80 (6)

* -0.0340 (0.0014) C21 * -0.0387 (0.0015) C22 * -0.0123 (0.0015) C23 * 0.0085 (0.0015) C24 * -0.0235 (0.0014) C25 * -0.0323 (0.0013) C26 * 0.0758 (0.0009) S1 * 0.0565 (0.0012) O24

Rms deviation of fitted atoms = 0.0409

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.82943 (7)0.55391 (4)0.74918 (4)0.04926 (16)
O111.02967 (18)0.56344 (13)0.79019 (12)0.0697 (4)
O120.7643 (2)0.62654 (11)0.69430 (11)0.0656 (4)
O140.5387 (2)0.06276 (10)0.39318 (11)0.0601 (4)
O240.51420 (19)0.69229 (14)1.15436 (11)0.0621 (4)
C110.7301 (2)0.40695 (15)0.64627 (14)0.0420 (4)
C120.7484 (2)0.31507 (15)0.67547 (14)0.0464 (4)
C130.6825 (3)0.20075 (16)0.59032 (15)0.0497 (4)
C140.5977 (2)0.17650 (15)0.47434 (14)0.0444 (4)
C150.5755 (3)0.26910 (16)0.44650 (15)0.0534 (5)
C160.6415 (3)0.38335 (16)0.53204 (15)0.0514 (5)
C210.7369 (2)0.58675 (14)0.87023 (14)0.0428 (4)
C220.8532 (3)0.61383 (17)0.98039 (16)0.0531 (5)
C230.7809 (3)0.64904 (18)1.07650 (16)0.0562 (5)
C240.5921 (3)0.65669 (15)1.06364 (14)0.0459 (4)
C250.4759 (2)0.62635 (15)0.95253 (15)0.0478 (4)
C260.5482 (2)0.59275 (15)0.85702 (14)0.0473 (4)
N310.3703 (12)0.0257 (5)0.1680 (3)0.0516 (15)0.771 (5)
C320.3394 (12)0.1049 (4)0.1295 (4)0.0742 (15)0.771 (5)
C330.2534 (8)0.0812 (3)0.0156 (3)0.0671 (10)0.771 (5)
C340.2030 (4)0.0317 (3)0.06983 (19)0.0483 (7)0.771 (5)
C350.2377 (6)0.1174 (3)0.0323 (3)0.0672 (10)0.771 (5)
C360.3215 (7)0.0854 (4)0.0865 (3)0.0622 (12)0.771 (5)
C370.1152 (4)0.0581 (2)0.1918 (2)0.0549 (7)0.771 (5)
N410.2424 (10)0.2480 (5)0.6352 (3)0.0597 (19)0.771 (5)
C420.1767 (8)0.3280 (3)0.6038 (3)0.0580 (8)0.771 (5)
C430.0798 (4)0.3025 (3)0.4912 (2)0.0515 (7)0.771 (5)
C440.0404 (3)0.1887 (3)0.40347 (19)0.0453 (6)0.771 (5)
C450.1048 (4)0.1049 (3)0.4355 (2)0.0596 (8)0.771 (5)
C460.2070 (6)0.1383 (4)0.5509 (3)0.0648 (10)0.771 (5)
C470.0600 (3)0.1622 (2)0.2827 (2)0.0504 (7)0.771 (5)
N510.354 (4)0.0287 (18)0.1726 (9)0.063 (7)*0.229 (5)
C520.297 (3)0.0852 (17)0.1039 (10)0.063 (2)*0.229 (5)
C530.217 (2)0.1375 (10)0.0154 (9)0.063 (2)*0.229 (5)
C540.1970 (17)0.0704 (8)0.0732 (6)0.041 (2)*0.229 (5)
C550.257 (3)0.0503 (9)0.0029 (11)0.063 (2)*0.229 (5)
C560.314 (4)0.0970 (14)0.1204 (11)0.063 (2)*0.229 (5)
C570.1067 (12)0.1262 (7)0.1995 (6)0.053 (2)*0.229 (5)
N610.231 (4)0.2414 (15)0.6349 (9)0.063 (7)*0.229 (5)
C620.194 (2)0.1247 (12)0.5680 (9)0.063 (2)*0.229 (5)
C630.1015 (17)0.0698 (8)0.4503 (8)0.063 (2)*0.229 (5)
C640.0379 (13)0.1359 (7)0.3948 (6)0.041 (2)*0.229 (5)
C650.073 (2)0.2563 (8)0.4629 (9)0.063 (2)*0.229 (5)
C660.171 (3)0.3057 (10)0.5815 (10)0.063 (2)*0.229 (5)
C670.0613 (11)0.0772 (7)0.2690 (6)0.053 (2)*0.229 (5)
H140.48580.05950.32940.090*
H240.59520.70871.21560.093*
H120.80540.33070.75280.056*
H130.69460.13920.61030.060*
H150.51580.25390.36970.064*
H160.62620.44520.51280.062*
H220.97970.60830.98940.064*
H230.85930.66781.15050.067*
H250.34830.62880.94270.057*
H260.46980.57390.78300.057*
H320.37930.18370.18440.089*0.771 (5)
H330.22980.14260.00300.080*0.771 (5)
H350.20490.19660.08680.081*0.771 (5)
H360.34370.14450.10910.075*0.771 (5)
H370.09620.00610.20660.066*0.771 (5)
H420.19810.40550.66170.070*0.771 (5)
H430.04050.36240.47410.062*0.771 (5)
H450.07970.02620.37990.072*0.771 (5)
H460.25270.08080.56980.078*0.771 (5)
H470.08750.22610.26930.060*0.771 (5)
H520.31190.13470.13980.075*0.229 (5)
H530.17710.21880.05660.075*0.229 (5)
H550.25890.10040.03800.075*0.229 (5)
H560.32480.17740.16640.075*0.229 (5)
H570.07740.20810.23560.063*0.229 (5)
H620.23450.07780.60370.075*0.229 (5)
H630.08170.01180.40820.075*0.229 (5)
H650.03170.30460.42920.075*0.229 (5)
H660.19540.38730.62520.075*0.229 (5)
H670.09580.00440.23470.063*0.229 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0547 (3)0.0437 (3)0.0353 (2)0.00104 (19)0.00831 (19)0.00829 (19)
O110.0483 (8)0.0751 (10)0.0499 (8)0.0056 (7)0.0093 (6)0.0001 (7)
O120.1037 (11)0.0448 (7)0.0469 (7)0.0051 (7)0.0206 (7)0.0207 (6)
O140.0824 (10)0.0410 (7)0.0394 (7)0.0053 (6)0.0051 (7)0.0084 (6)
O240.0586 (8)0.0849 (10)0.0385 (7)0.0176 (7)0.0118 (6)0.0240 (7)
C110.0416 (9)0.0433 (9)0.0321 (8)0.0057 (7)0.0052 (7)0.0111 (7)
C120.0510 (10)0.0521 (10)0.0305 (8)0.0067 (8)0.0049 (7)0.0167 (8)
C130.0613 (11)0.0450 (10)0.0411 (10)0.0083 (8)0.0100 (8)0.0198 (8)
C140.0477 (10)0.0409 (9)0.0351 (9)0.0062 (7)0.0082 (7)0.0102 (7)
C150.0623 (12)0.0518 (11)0.0317 (9)0.0086 (9)0.0025 (8)0.0130 (8)
C160.0636 (12)0.0430 (10)0.0387 (9)0.0114 (8)0.0017 (8)0.0160 (8)
C210.0481 (10)0.0371 (9)0.0324 (8)0.0044 (7)0.0037 (7)0.0097 (7)
C220.0473 (10)0.0655 (12)0.0413 (10)0.0153 (9)0.0055 (8)0.0216 (9)
C230.0532 (11)0.0756 (13)0.0341 (9)0.0156 (10)0.0014 (8)0.0237 (9)
C240.0521 (10)0.0472 (10)0.0355 (9)0.0088 (8)0.0074 (8)0.0182 (8)
C250.0420 (10)0.0493 (10)0.0406 (10)0.0063 (8)0.0021 (8)0.0143 (8)
C260.0497 (10)0.0454 (10)0.0308 (9)0.0028 (8)0.0037 (7)0.0104 (7)
N310.060 (2)0.0457 (19)0.0315 (15)0.0075 (11)0.0033 (11)0.0064 (10)
C320.102 (4)0.0460 (17)0.0426 (16)0.0030 (17)0.0095 (16)0.0073 (13)
C330.097 (2)0.0458 (17)0.0417 (17)0.005 (2)0.0010 (17)0.0148 (14)
C340.0502 (15)0.0453 (18)0.0395 (14)0.0034 (15)0.0030 (10)0.0152 (13)
C350.092 (3)0.0415 (16)0.0365 (15)0.0006 (16)0.0017 (15)0.0009 (13)
C360.080 (3)0.0492 (15)0.0393 (17)0.0136 (16)0.0031 (16)0.0091 (14)
C370.0655 (17)0.0474 (15)0.0426 (14)0.0074 (12)0.0032 (12)0.0177 (12)
N410.0457 (19)0.091 (3)0.0318 (15)0.0132 (13)0.0071 (9)0.0198 (13)
C420.0534 (16)0.064 (2)0.0386 (16)0.0039 (17)0.0106 (15)0.0090 (14)
C430.0507 (14)0.0563 (17)0.0413 (15)0.0052 (15)0.0090 (12)0.0189 (13)
C440.0404 (13)0.0507 (18)0.0390 (13)0.0029 (13)0.0076 (10)0.0174 (13)
C450.0661 (18)0.0535 (17)0.0421 (14)0.0088 (15)0.0036 (13)0.0116 (13)
C460.065 (2)0.078 (2)0.0497 (19)0.0211 (16)0.0087 (15)0.0297 (16)
C470.0544 (15)0.0504 (15)0.0387 (13)0.0044 (11)0.0055 (11)0.0173 (11)
Geometric parameters (Å, º) top
S1—O111.4397 (14)C35—C361.399 (4)
S1—O121.4409 (14)C37—C471.308 (3)
S1—C111.7585 (17)N41—C421.335 (5)
S1—C211.7516 (17)N41—C461.323 (5)
O14—C141.349 (2)C42—C431.369 (4)
O24—C241.344 (2)C43—C441.373 (4)
C11—C121.383 (2)C44—C451.381 (4)
C11—C161.379 (2)C44—C471.464 (3)
C12—C131.373 (2)C45—C461.388 (4)
C13—C141.390 (2)N51—C521.317 (7)
C14—C151.384 (3)N51—C561.325 (6)
C15—C161.374 (2)C52—C531.368 (7)
C21—C221.385 (2)C53—C541.353 (6)
C21—C261.381 (2)C54—C551.391 (6)
C22—C231.377 (3)C54—C571.456 (5)
C23—C241.386 (3)C55—C561.402 (6)
C24—C251.386 (2)C57—C671.303 (5)
C25—C261.371 (2)N61—C621.337 (7)
N31—C321.317 (4)N61—C661.324 (7)
N31—C361.322 (4)C62—C631.369 (6)
C32—C331.370 (4)C63—C641.370 (5)
C33—C341.354 (4)C64—C651.378 (6)
C34—C351.391 (4)C64—C671.464 (5)
C34—C371.457 (3)C65—C661.389 (6)
O11—S1—O12117.84 (9)C35—C34—C37123.8 (2)
O11—S1—C11108.82 (8)C34—C35—C36120.6 (3)
O11—S1—C21107.58 (8)N31—C36—C35122.5 (3)
O12—S1—C11106.86 (8)C34—C37—C47127.1 (2)
O12—S1—C21107.90 (8)C42—N41—C46116.5 (2)
C11—S1—C21107.42 (8)N41—C42—C43123.8 (3)
S1—C11—C12121.72 (12)C42—C43—C44120.1 (3)
S1—C11—C16118.45 (13)C43—C44—C45116.5 (2)
C12—C11—C16119.72 (16)C43—C44—C47119.9 (2)
C11—C12—C13120.04 (15)C45—C44—C47123.6 (2)
C12—C13—C14120.37 (16)C44—C45—C46119.9 (3)
O14—C14—C15122.50 (15)N41—C46—C45123.1 (3)
O14—C14—C13118.30 (16)C37—C47—C44126.8 (2)
C13—C14—C15119.20 (16)C52—N51—C56115.2 (6)
C14—C15—C16120.19 (16)N51—C52—C53126.0 (8)
C11—C16—C15120.43 (17)C52—C53—C54119.7 (7)
S1—C21—C22120.63 (14)C53—C54—C55115.5 (5)
S1—C21—C26119.48 (13)C53—C54—C57119.4 (6)
C22—C21—C26119.77 (16)C55—C54—C57124.9 (6)
C21—C22—C23119.82 (17)C54—C55—C56120.5 (7)
C22—C23—C24120.44 (16)N51—C56—C55121.3 (8)
O24—C24—C25117.56 (16)C54—C57—C67128.9 (6)
O24—C24—C23123.18 (15)C62—N61—C66116.4 (6)
C23—C24—C25119.27 (16)N61—C62—C63124.3 (7)
C24—C25—C26120.32 (17)C62—C63—C64119.6 (6)
C21—C26—C25120.34 (16)C63—C64—C65116.8 (5)
C32—N31—C36115.6 (2)C63—C64—C67119.6 (5)
N31—C32—C33125.6 (3)C65—C64—C67123.6 (5)
C32—C33—C34120.0 (3)C64—C65—C66120.3 (6)
C33—C34—C35115.7 (2)N61—C66—C65122.6 (7)
C33—C34—C37120.6 (3)C57—C67—C64127.4 (6)
O11—S1—C11—C16117.56 (15)C37—C34—C35—C36179.6 (3)
O12—S1—C11—C1610.68 (17)C32—N31—C36—C351.7 (8)
C21—S1—C11—C16126.25 (15)C34—C35—C36—N310.3 (6)
O11—S1—C11—C1258.64 (17)C33—C34—C37—C47179.8 (4)
O12—S1—C11—C12173.12 (14)C35—C34—C37—C471.4 (5)
C21—S1—C11—C1257.55 (16)C46—N41—C42—C431.0 (9)
C16—C11—C12—C131.5 (3)N41—C42—C43—C441.8 (8)
S1—C11—C12—C13174.62 (14)C42—C43—C44—C450.6 (5)
C11—C12—C13—C140.3 (3)C42—C43—C44—C47178.8 (4)
C12—C13—C14—O14178.62 (16)C43—C44—C45—C461.3 (4)
C12—C13—C14—C151.9 (3)C47—C44—C45—C46176.8 (3)
O14—C14—C15—C16178.75 (18)C42—N41—C46—C451.1 (7)
C13—C14—C15—C161.8 (3)C44—C45—C46—N412.2 (5)
C14—C15—C16—C110.1 (3)C34—C37—C47—C44175.2 (3)
C12—C11—C16—C151.6 (3)C43—C44—C47—C37176.4 (3)
S1—C11—C16—C15174.64 (15)C45—C44—C47—C375.5 (4)
O11—S1—C21—C26175.13 (14)C56—N51—C52—C536 (2)
O12—S1—C21—C2647.01 (16)N51—C52—C53—C542.0 (15)
C11—S1—C21—C2667.86 (15)C52—C53—C54—C552 (2)
O11—S1—C21—C220.85 (18)C52—C53—C54—C57178.1 (12)
O12—S1—C21—C22128.96 (15)C53—C54—C55—C567 (3)
C11—S1—C21—C22116.16 (16)C57—C54—C55—C56169.7 (17)
C26—C21—C22—C231.4 (3)C52—N51—C56—C5514 (3)
S1—C21—C22—C23174.56 (15)C54—C55—C56—N5115 (4)
C21—C22—C23—C240.5 (3)C53—C54—C57—C67174.3 (12)
C22—C23—C24—O24178.89 (18)C55—C54—C57—C672 (2)
C22—C23—C24—C251.2 (3)C66—N61—C62—C630 (2)
O24—C24—C25—C26178.04 (17)N61—C62—C63—C640.8 (13)
C23—C24—C25—C262.1 (3)C62—C63—C64—C650.3 (18)
C24—C25—C26—C211.2 (3)C62—C63—C64—C67180.0 (10)
C22—C21—C26—C250.6 (3)C63—C64—C65—C661 (2)
S1—C21—C26—C25175.45 (14)C67—C64—C65—C66179.0 (15)
C36—N31—C32—C333.6 (12)C62—N61—C66—C651 (3)
N31—C32—C33—C344.2 (12)C64—C65—C66—N611 (3)
C32—C33—C34—C352.4 (8)C54—C57—C67—C64176.8 (11)
C32—C33—C34—C37178.7 (6)C63—C64—C67—C57169.4 (10)
C33—C34—C35—C360.7 (6)C65—C64—C67—C5710.2 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N310.821.932.743 (4)171
O14—H14···N510.821.922.730 (7)172
O24—H24···N41i0.821.872.688 (5)173
O24—H24···N61i0.821.902.714 (7)174
C16—H16···O120.932.442.848 (2)107
C22—H22···O110.932.522.898 (2)104
C25—H25···O11ii0.932.553.344 (2)144
Symmetry codes: (i) x+1, y+1, z+2; (ii) x1, y, z.
(6c) 4,4'Sulfonyldiphenol–1,2-bis(4-pyridyl)ethane (1/1) top
Crystal data top
C12H10O4S·C12H12N2F(000) = 456
Mr = 434.50? #Insert any comments here.
Triclinic, P1Dx = 1.329 Mg m3
a = 7.7599 (9) ÅMo Kα radiation, λ = 0.7107 Å
b = 12.4866 (16) ÅCell parameters from 25 reflections
c = 12.914 (2) Åθ = 9.8–22.5°
α = 114.003 (14)°µ = 0.18 mm1
β = 104.694 (14)°T = 294 K
γ = 93.690 (13)°Plate, colourless
V = 1085.7 (3) Å30.42 × 0.42 × 0.32 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
3905 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.000
Graphite monochromatorθmax = 27.4°, θmin = 2.8°
θ/2θ scansh = 109
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
k = 016
Tmin = 0.934, Tmax = 0.951l = 1615
4973 measured reflections3 standard reflections every 120 min
4973 independent reflections intensity decay: no decay, variation 0.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.2544P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4973 reflectionsΔρmax = 0.43 e Å3
283 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (2)
Crystal data top
C12H10O4S·C12H12N2γ = 93.690 (13)°
Mr = 434.50V = 1085.7 (3) Å3
Triclinic, P1Z = 2
a = 7.7599 (9) ÅMo Kα radiation
b = 12.4866 (16) ŵ = 0.18 mm1
c = 12.914 (2) ÅT = 294 K
α = 114.003 (14)°0.42 × 0.42 × 0.32 mm
β = 104.694 (14)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3905 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
Rint = 0.000
Tmin = 0.934, Tmax = 0.9513 standard reflections every 120 min
4973 measured reflections intensity decay: no decay, variation 0.7%
4973 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.07Δρmax = 0.43 e Å3
4973 reflectionsΔρmin = 0.32 e Å3
283 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data ex last SHELXL run.

Equivalent position indicated by $1 is: -x, -y, -z Equivalent position indicated by $2 is: 1 - x, 1 - y, 2 - z

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.4936 (0.0024) x + 0.4452 (0.0097) y - 6.4003 (0.0090) z = 1.4297 (0.0052)

* 0.0143 (0.0012) C11 * -0.0090 (0.0012) C12 * -0.0070 (0.0013) C13 * 0.0178 (0.0012) C14 * -0.0127 (0.0013) C15 * -0.0034 (0.0013) C16 - 3.5241 (0.0020) N41_$1 - 3.8413 (0.0025) C42_$1 - 4.0056 (0.0029) C43_$1 - 3.8641 (0.0030) C44_$1 - 3.5478 (0.0033) C45_$1 - 3.3698 (0.0029) C46_$1

Rms deviation of fitted atoms = 0.0117

- 6.9555 (0.0034) x - 3.1748 (0.0121) y + 8.1781 (0.0082) z = 2.6502 (0.0046)

Angle to previous plane (with approximate e.s.d.) = 13.63 (0.07)

* 0.0013 (0.0014) N41_$1 * 0.0069 (0.0014) C42_$1 * -0.0072 (0.0014) C43_$1 * -0.0002 (0.0014) C44_$1 * 0.0081 (0.0017) C45_$1 * -0.0089 (0.0017) C46_$1 - 3.6553 (0.0029) C11 - 3.3077 (0.0032) C12 - 3.1802 (0.0033) C13 - 3.3989 (0.0027) C14 - 3.6925 (0.0023) C15 - 3.8300 (0.0026) C16

Rms deviation of fitted atoms = 0.0064

0.9838 (0.0053) x + 11.9886 (0.0039) y - 3.4143 (0.0089) z = 4.7874 (0.0075)

Angle to previous plane (with approximate e.s.d.) = 69.38 (0.07)

* 0.0045 (0.0011) C21 * -0.0055 (0.0013) C22 * 0.0007 (0.0013) C23 * 0.0050 (0.0012) C24 * -0.0061 (0.0011) C25 * 0.0013 (0.0011) C26 - 3.4355 (0.0027) C21_$2 - 3.4255 (0.0026) C22_$2 - 3.4317 (0.0028) C23_$2 - 3.4360 (0.0026) C24_$2 - 3.4249 (0.0026) C25_$2 - 3.4323 (0.0026) C26_$2

Rms deviation of fitted atoms = 0.0044

0.9838 (0.0053) x + 11.9886 (0.0039) y - 3.4143 (0.0089) z = 1.3564 (0.0085)

Angle to previous plane (with approximate e.s.d.) = 0.00 (0.06)

* -0.0045 (0.0011) C21_$2 * 0.0055 (0.0013) C22_$2 * -0.0007 (0.0013) C23_$2 * -0.0050 (0.0012) C24_$2 * 0.0061 (0.0011) C25_$2 * -0.0013 (0.0011) C26_$2 3.4355 (0.0027) C21 3.4255 (0.0026) C22 3.4317 (0.0028) C23 3.4360 (0.0026) C24 3.4249 (0.0026) C25 3.4323 (0.0026) C26

Rms deviation of fitted atoms = 0.0044

7.1628 (0.0026) x - 2.3267 (0.0111) y - 6.4033 (0.0073) z = 1.7542 (0.0010)

Angle to previous plane (with approximate e.s.d.) = 85.34 (0.07)

* -0.0335 (0.0013) N31 * -0.0009 (0.0014) C32 * 0.0281 (0.0016) C33 * 0.0148 (0.0017) C34 * 0.0279 (0.0016) C35 * 0.0001 (0.0014) C36 * -0.0364 (0.0012) C37

Rms deviation of fitted atoms = 0.0246

6.9514 (0.0031) x + 3.1777 (0.0120) y - 8.1923 (0.0063) z = 2.6580 (0.0034)

Angle to previous plane (with approximate e.s.d.) = 25.62 (0.06)

* 0.0028 (0.0015) N41 * 0.0074 (0.0014) C42 * -0.0086 (0.0016) C43 * -0.0027 (0.0017) C44 * 0.0066 (0.0019) C45 * -0.0084 (0.0017) C46 * 0.0029 (0.0013) C47

Rms deviation of fitted atoms = 0.0062

5.1493 (0.0066) x - 7.7839 (0.0106) y + 6.2915 (0.0109) z = 4.6645 (0.0073)

Angle to previous plane (with approximate e.s.d.) = 74.69 (0.06)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

7.4831 (0.0024) x + 0.3349 (0.0075) y - 6.4452 (0.0088) z = 1.3918 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 61.91 (0.06)

* -0.0295 (0.0013) C11 * -0.0441 (0.0013) C12 * -0.0248 (0.0014) C13 * 0.0089 (0.0015) C14 * -0.0304 (0.0014) C15 * -0.0384 (0.0014) C16 * 0.0859 (0.0009) S1 * 0.0723 (0.0011) O14

Rms deviation of fitted atoms = 0.0481

5.1493 (0.0066) x - 7.7839 (0.0106) y + 6.2915 (0.0109) z = 4.6645 (0.0073)

Angle to previous plane (with approximate e.s.d.) = 61.91 (0.06)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

0.9343 (0.0045) x + 11.9817 (0.0039) y - 3.2961 (0.0054) z = 4.8780 (0.0059)

Angle to previous plane (with approximate e.s.d.) = 67.46 (0.06)

* -0.0232 (0.0013) C21 * -0.0254 (0.0014) C22 * -0.0048 (0.0014) C23 * 0.0062 (0.0014) C24 * -0.0127 (0.0012) C25 * -0.0197 (0.0012) C26 * 0.0472 (0.0008) S1 * 0.0323 (0.0011) O24

Rms deviation of fitted atoms = 0.0252

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.82235 (6)0.55444 (4)0.75430 (4)0.04529 (14)
O111.01380 (17)0.56195 (12)0.80197 (12)0.0637 (4)
O120.7644 (2)0.62870 (11)0.69620 (12)0.0644 (4)
O140.5356 (2)0.05715 (11)0.39760 (11)0.0590 (4)
O240.50738 (18)0.68579 (13)1.14705 (11)0.0567 (3)
C110.7243 (2)0.40583 (14)0.65068 (13)0.0391 (3)
C120.7524 (2)0.31208 (15)0.68072 (14)0.0447 (4)
C130.6869 (3)0.19626 (15)0.59558 (15)0.0491 (4)
C140.5920 (2)0.17269 (14)0.47903 (14)0.0429 (4)
C150.5584 (2)0.26648 (16)0.45090 (14)0.0491 (4)
C160.6256 (3)0.38222 (15)0.53616 (14)0.0481 (4)
C210.7297 (2)0.58808 (13)0.87172 (13)0.0388 (3)
C220.8382 (2)0.61042 (16)0.98433 (15)0.0480 (4)
C230.7659 (2)0.64345 (17)1.07763 (15)0.0518 (4)
C240.5848 (2)0.65341 (14)1.05917 (14)0.0419 (4)
C250.4755 (2)0.62909 (14)0.94553 (14)0.0437 (4)
C260.5482 (2)0.59739 (14)0.85305 (14)0.0429 (4)
N310.3942 (2)0.01783 (13)0.16574 (12)0.0483 (3)
C320.3800 (3)0.09352 (16)0.11731 (16)0.0537 (4)
C330.2733 (3)0.06495 (18)0.00375 (16)0.0560 (5)
C340.1713 (3)0.04915 (17)0.06678 (15)0.0523 (4)
C350.1904 (3)0.12917 (16)0.01837 (16)0.0568 (5)
C360.3010 (3)0.09299 (16)0.09651 (16)0.0522 (4)
C370.0424 (3)0.0851 (2)0.18997 (17)0.0691 (6)
N410.2507 (2)0.26148 (17)0.63894 (13)0.0607 (4)
C420.1746 (3)0.3384 (2)0.60482 (17)0.0618 (5)
C430.0589 (3)0.30801 (19)0.49284 (16)0.0582 (5)
C440.0141 (2)0.19092 (19)0.41014 (15)0.0549 (5)
C450.0911 (3)0.1100 (2)0.44520 (19)0.0703 (6)
C460.2100 (3)0.1488 (2)0.55931 (19)0.0703 (6)
C470.1154 (3)0.1543 (2)0.28671 (17)0.0700 (6)
H140.49810.05380.33080.089*
H240.58300.69721.20960.085*
H120.81560.32770.75850.054*
H130.70580.13350.61570.059*
H150.49020.25130.37420.059*
H160.60430.44500.51650.058*
H220.95950.60320.99700.058*
H230.83900.65911.15330.062*
H250.35340.63430.93220.052*
H260.47530.58210.77740.052*
H320.44660.17080.16310.064*
H330.26940.12180.02560.067*
H350.12870.20780.06320.068*
H360.31100.14880.12720.063*
H37A0.06950.13230.19910.083*
H37B0.01330.01370.19740.083*
H420.20120.41820.66010.074*
H430.01150.36640.47350.070*
H450.06340.02930.39240.084*
H460.26310.09290.58040.084*
H47A0.14510.22560.27900.084*
H47B0.22700.10700.27790.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0500 (3)0.0392 (2)0.0382 (2)0.00062 (16)0.01294 (17)0.01030 (16)
O110.0438 (7)0.0654 (8)0.0552 (8)0.0044 (6)0.0137 (6)0.0038 (6)
O120.0994 (11)0.0450 (7)0.0531 (8)0.0071 (7)0.0283 (8)0.0236 (6)
O140.0811 (10)0.0418 (6)0.0369 (6)0.0001 (6)0.0067 (6)0.0091 (5)
O240.0539 (8)0.0759 (9)0.0389 (6)0.0187 (7)0.0144 (6)0.0227 (6)
C110.0393 (8)0.0390 (8)0.0324 (7)0.0059 (6)0.0096 (6)0.0103 (6)
C120.0498 (9)0.0473 (9)0.0306 (7)0.0039 (7)0.0054 (7)0.0157 (7)
C130.0635 (11)0.0426 (9)0.0391 (8)0.0064 (8)0.0107 (8)0.0193 (7)
C140.0445 (9)0.0415 (8)0.0342 (8)0.0035 (7)0.0099 (6)0.0105 (6)
C150.0533 (10)0.0526 (9)0.0302 (7)0.0161 (8)0.0026 (7)0.0125 (7)
C160.0588 (10)0.0440 (9)0.0372 (8)0.0189 (8)0.0088 (7)0.0159 (7)
C210.0434 (8)0.0322 (7)0.0337 (7)0.0044 (6)0.0076 (6)0.0104 (6)
C220.0405 (9)0.0599 (10)0.0420 (8)0.0153 (8)0.0069 (7)0.0233 (8)
C230.0477 (10)0.0686 (12)0.0352 (8)0.0146 (8)0.0040 (7)0.0237 (8)
C240.0451 (9)0.0412 (8)0.0367 (8)0.0087 (7)0.0097 (7)0.0160 (7)
C250.0372 (8)0.0449 (9)0.0394 (8)0.0073 (7)0.0039 (6)0.0137 (7)
C260.0434 (9)0.0404 (8)0.0314 (7)0.0031 (6)0.0002 (6)0.0103 (6)
N310.0497 (8)0.0463 (8)0.0347 (7)0.0046 (6)0.0056 (6)0.0091 (6)
C320.0593 (11)0.0422 (9)0.0441 (9)0.0019 (8)0.0073 (8)0.0108 (7)
C330.0687 (12)0.0537 (10)0.0436 (9)0.0106 (9)0.0139 (8)0.0214 (8)
C340.0524 (10)0.0563 (10)0.0341 (8)0.0165 (8)0.0091 (7)0.0080 (8)
C350.0596 (11)0.0406 (9)0.0450 (9)0.0019 (8)0.0024 (8)0.0036 (7)
C360.0599 (11)0.0423 (9)0.0450 (9)0.0086 (8)0.0100 (8)0.0138 (7)
C370.0633 (13)0.0865 (15)0.0401 (10)0.0262 (11)0.0071 (9)0.0144 (10)
N410.0490 (9)0.0903 (13)0.0355 (7)0.0141 (8)0.0103 (6)0.0222 (8)
C420.0556 (11)0.0707 (13)0.0414 (10)0.0051 (10)0.0104 (8)0.0114 (9)
C430.0549 (11)0.0718 (13)0.0449 (10)0.0135 (9)0.0130 (8)0.0239 (9)
C440.0418 (9)0.0790 (13)0.0366 (8)0.0129 (9)0.0105 (7)0.0190 (9)
C450.0744 (14)0.0667 (13)0.0475 (11)0.0143 (11)0.0075 (10)0.0102 (10)
C460.0733 (14)0.0842 (16)0.0515 (11)0.0258 (12)0.0120 (10)0.0306 (11)
C470.0533 (12)0.1002 (17)0.0385 (9)0.0218 (11)0.0068 (8)0.0165 (10)
Geometric parameters (Å, º) top
S1—O111.4373 (14)C25—C261.374 (2)
S1—O121.4399 (14)N31—C321.325 (2)
S1—C111.7591 (16)N31—C361.332 (2)
S1—C211.7510 (17)C32—C331.373 (3)
O14—C141.3528 (19)C33—C341.385 (3)
O24—C241.347 (2)C34—C351.375 (3)
C11—C121.388 (2)C34—C371.512 (2)
C11—C161.379 (2)C35—C361.378 (3)
C12—C131.374 (2)C37—C471.474 (3)
C13—C141.394 (2)N41—C421.323 (3)
C14—C151.382 (2)N41—C461.318 (3)
C15—C161.375 (2)C42—C431.376 (3)
C21—C221.386 (2)C43—C441.369 (3)
C21—C261.388 (2)C44—C451.377 (3)
C22—C231.381 (2)C44—C471.515 (2)
C23—C241.387 (2)C45—C461.389 (3)
C24—C251.392 (2)
O11—S1—O12118.23 (9)O24—C24—C25117.50 (15)
O11—S1—C11108.62 (8)C23—C24—C25119.60 (15)
O12—S1—C11107.03 (8)C24—C25—C26119.87 (15)
O11—S1—C21107.41 (8)C21—C26—C25120.49 (14)
O12—S1—C21107.97 (8)C32—N31—C36116.34 (15)
C11—S1—C21107.10 (7)N31—C32—C33124.09 (17)
S1—C11—C12121.06 (12)C32—C33—C34119.55 (18)
S1—C11—C16119.12 (13)C33—C34—C35116.54 (16)
C12—C11—C16119.74 (15)C33—C34—C37122.54 (19)
C11—C12—C13119.97 (15)C35—C34—C37120.91 (18)
C12—C13—C14120.09 (16)C34—C35—C36120.09 (17)
O14—C14—C13117.83 (15)N31—C36—C35123.32 (17)
O14—C14—C15122.58 (15)C34—C37—C47113.61 (17)
C13—C14—C15119.58 (15)C42—N41—C46116.77 (17)
C14—C15—C16120.05 (15)N41—C42—C43124.2 (2)
C11—C16—C15120.47 (16)C42—C43—C44119.3 (2)
S1—C21—C22120.42 (13)C43—C44—C45116.85 (17)
S1—C21—C26119.75 (12)C43—C44—C47120.6 (2)
C22—C21—C26119.78 (15)C45—C44—C47122.6 (2)
C21—C22—C23119.83 (16)C44—C45—C46120.1 (2)
C22—C23—C24120.42 (15)N41—C46—C45122.7 (2)
O24—C24—C23122.90 (15)C37—C47—C44113.62 (17)
O11—S1—C11—C16124.45 (15)O24—C24—C25—C26179.04 (15)
O12—S1—C11—C164.25 (16)C23—C24—C25—C261.1 (3)
C21—S1—C11—C16119.84 (14)C24—C25—C26—C210.7 (2)
O11—S1—C11—C1252.30 (16)C22—C21—C26—C250.3 (2)
O12—S1—C11—C12179.00 (14)S1—C21—C26—C25177.01 (12)
C21—S1—C11—C1263.41 (15)C36—N31—C32—C331.8 (3)
C16—C11—C12—C132.0 (3)N31—C32—C33—C340.4 (3)
S1—C11—C12—C13174.69 (14)C32—C33—C34—C352.6 (3)
C11—C12—C13—C140.0 (3)C32—C33—C34—C37176.35 (19)
C12—C13—C14—O14177.82 (16)C33—C34—C35—C362.5 (3)
C12—C13—C14—C152.5 (3)C37—C34—C35—C36176.42 (18)
O14—C14—C15—C16177.29 (17)C32—N31—C36—C351.9 (3)
C13—C14—C15—C163.1 (3)C34—C35—C36—N310.3 (3)
C14—C15—C16—C111.1 (3)C35—C34—C37—C4779.2 (3)
C12—C11—C16—C151.5 (3)C33—C34—C37—C47101.9 (3)
S1—C11—C16—C15175.29 (14)C46—N41—C42—C430.5 (3)
O11—S1—C21—C222.71 (17)N41—C42—C43—C441.4 (3)
O12—S1—C21—C22131.23 (14)C42—C43—C44—C450.6 (3)
C11—S1—C21—C22113.81 (14)C42—C43—C44—C47178.99 (19)
O11—S1—C21—C26174.56 (13)C43—C44—C45—C460.9 (3)
O12—S1—C21—C2646.04 (15)C47—C44—C45—C46179.6 (2)
C11—S1—C21—C2668.92 (14)C42—N41—C46—C451.1 (3)
C26—C21—C22—C230.9 (3)C44—C45—C46—N411.8 (4)
S1—C21—C22—C23176.34 (14)C34—C37—C47—C44179.7 (2)
C21—C22—C23—C240.6 (3)C43—C44—C47—C37126.6 (2)
C22—C23—C24—O24179.70 (17)C45—C44—C47—C3753.9 (3)
C22—C23—C24—C250.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N310.821.922.735 (2)170
O24—H24···N41i0.821.892.706 (2)174
C16—H16···O120.932.462.859 (2)106
C22—H22···O110.932.512.889 (2)105
C46—H46···O14ii0.932.573.476 (3)164
Symmetry codes: (i) x+1, y+1, z+2; (ii) x1, y, z1.
(6d) 4,4'-Sulfonyldiphenol–4,4'-trimethylenedipyridine (1/1) top
Crystal data top
C12H10O4S·C13H14N2F(000) = 944
Mr = 448.52? #Insert any comments here.
Monoclinic, P21/cDx = 1.317 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.7107 Å
a = 10.0292 (10) ÅCell parameters from 10602 reflections
b = 15.579 (2) Åθ = 2.6–30.3°
c = 15.0208 (10) ŵ = 0.18 mm1
β = 105.4699 (10)°T = 150 K
V = 2261.9 (4) Å3Block cut from larger piece, colourless
Z = 40.30 × 0.30 × 0.30 mm
Data collection top
Enraf-Nonius KappaCCD
diffractometer
3828 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.031
Graphite monochromatorθmax = 30.2°, θmin = 2.6°
ω scansh = 1212
10602 measured reflectionsk = 1919
5465 independent reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.062P)2 + 0.2027P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5465 reflectionsΔρmax = 0.27 e Å3
292 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0066 (14)
Crystal data top
C12H10O4S·C13H14N2V = 2261.9 (4) Å3
Mr = 448.52Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0292 (10) ŵ = 0.18 mm1
b = 15.579 (2) ÅT = 150 K
c = 15.0208 (10) Å0.30 × 0.30 × 0.30 mm
β = 105.4699 (10)°
Data collection top
Enraf-Nonius KappaCCD
diffractometer
3828 reflections with I > 2σ(I)
10602 measured reflectionsRint = 0.031
5465 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å3
5465 reflectionsΔρmin = 0.36 e Å3
292 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean-plane calculations from final SHELXL run

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.8903 (0.0052) x - 8.3115 (0.0145) y - 9.8944 (0.0138) z = 0.0933 (0.0019)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12

Rms deviation of fitted atoms = 0.0000

7.2284 (0.0052) x + 8.0318 (0.0126) y + 3.8210 (0.0131) z = 2.6926 (0.0005)

Angle to previous plane (with approximate e.s.d.) = 89.51 (0.06)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

- 3.9991 (0.0054) x - 2.6996 (0.0065) y + 14.6344 (0.0029) z = 0.1858 (0.0020)

Angle to previous plane (with approximate e.s.d.) = 87.67 (0.06)

* 0.0234 (0.0013) C11 * -0.0001 (0.0012) C12 * -0.0081 (0.0013) C13 * -0.0051 (0.0015) C14 * -0.0148 (0.0013) C15 * 0.0062 (0.0012) C16 * -0.0108 (0.0007) S1 * 0.0094 (0.0011) O14

Rms deviation of fitted atoms = 0.0117

7.2284 (0.0052) x + 8.0318 (0.0126) y + 3.8210 (0.0131) z = 2.6926 (0.0005)

Angle to previous plane (with approximate e.s.d.) = 87.67 (0.06)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

- 2.6440 (0.0054) x + 14.9139 (0.0034) y - 0.6618 (0.0039) z = 0.4068 (0.0019)

Angle to previous plane (with approximate e.s.d.) = 75.61 (0.05)

* -0.0257 (0.0012) C21 * -0.0302 (0.0012) C22 * -0.0132 (0.0012) C23 * 0.0071 (0.0012) C24 * -0.0165 (0.0011) C25 * -0.0244 (0.0011) C26 * 0.0586 (0.0007) S1 * 0.0442 (0.0009) O24

Rms deviation of fitted atoms = 0.0317

- 3.2131 (0.0059) x + 9.2026 (0.0086) y + 12.0044 (0.0063) z = 4.5255 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 55.80 (0.04)

* 0.0041 (0.0010) N31 * -0.0016 (0.0012) C32 * -0.0038 (0.0012) C33 * 0.0067 (0.0010) C34 * -0.0043 (0.0011) C35 * -0.0011 (0.0011) C36 0.0896 (0.0026) C51 - 0.4867 (0.0029) C52 - 0.3405 (0.0037) C53

Rms deviation of fitted atoms = 0.0040

1.1888 (0.0066) x + 0.2105 (0.0107) y - 14.8481 (0.0024) z = 2.0016 (0.0089)

Angle to previous plane (with approximate e.s.d.) = 40.07 (0.05)

* -0.0034 (0.0011) N41 * -0.0019 (0.0012) C42 * 0.0068 (0.0011) C43 * -0.0066 (0.0011) C44 * 0.0016 (0.0012) C45 * 0.0035 (0.0012) C46 - 0.6781 (0.0037) C51 - 0.5929 (0.0029) C52 - 0.0347 (0.0026) C53

Rms deviation of fitted atoms = 0.0045

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.23814 (4)0.07748 (3)0.09133 (3)0.03407 (12)
O110.14797 (12)0.00489 (8)0.08950 (9)0.0437 (3)
O120.35940 (12)0.08684 (8)0.16790 (8)0.0439 (3)
O140.08787 (12)0.39407 (8)0.06202 (10)0.0508 (3)
O240.40552 (11)0.09085 (7)0.25431 (7)0.0353 (3)
C110.13838 (15)0.17092 (10)0.08364 (10)0.0304 (3)
C120.00415 (15)0.16806 (10)0.04256 (11)0.0356 (4)
C130.08130 (16)0.24228 (11)0.03462 (12)0.0376 (4)
C140.01805 (15)0.31998 (10)0.06644 (11)0.0357 (4)
C150.12475 (15)0.32275 (11)0.10531 (12)0.0368 (4)
C160.20157 (15)0.24850 (11)0.11404 (10)0.0340 (3)
C210.29251 (14)0.07695 (9)0.01041 (10)0.0285 (3)
C220.19855 (15)0.05628 (10)0.09397 (11)0.0337 (3)
C230.23872 (15)0.06097 (10)0.17438 (11)0.0327 (3)
C240.37310 (15)0.08622 (9)0.17296 (10)0.0283 (3)
C250.46723 (15)0.10506 (10)0.08879 (11)0.0318 (3)
C260.42692 (15)0.10098 (9)0.00785 (11)0.0316 (3)
N310.35849 (13)0.38411 (9)0.01309 (10)0.0361 (3)
C320.45180 (16)0.32954 (11)0.00330 (12)0.0397 (4)
C330.59206 (16)0.33550 (10)0.03900 (12)0.0362 (4)
C340.64118 (15)0.40102 (9)0.10150 (10)0.0289 (3)
C350.54310 (15)0.45700 (10)0.11908 (10)0.0316 (3)
C360.40596 (16)0.44668 (10)0.07419 (11)0.0343 (3)
N411.36352 (13)0.18273 (9)0.24115 (9)0.0374 (3)
C421.38586 (16)0.26732 (11)0.24185 (12)0.0411 (4)
C431.28353 (15)0.32759 (11)0.23339 (11)0.0361 (4)
C441.14730 (14)0.30164 (10)0.22194 (10)0.0300 (3)
C451.12389 (15)0.21389 (10)0.22187 (12)0.0368 (4)
C461.23335 (16)0.15735 (11)0.23156 (12)0.0395 (4)
C510.79200 (15)0.41627 (10)0.14664 (12)0.0357 (4)
C520.88803 (14)0.33905 (10)0.16117 (11)0.0305 (3)
C531.03420 (15)0.36768 (10)0.21006 (12)0.0373 (4)
H140.17020.38560.03770.076*
H240.48320.11130.24610.053*
H120.04670.11630.02070.043*
H130.17620.24040.00780.045*
H150.16800.37470.12530.044*
H160.29660.25050.14050.041*
H220.10910.03940.09540.040*
H230.17600.04720.23030.039*
H250.55750.12040.08710.038*
H260.48960.11430.04820.038*
H320.42100.28530.04530.048*
H330.65300.29570.02550.043*
H350.57070.50140.16130.038*
H360.34260.48520.08690.041*
H421.47580.28640.24840.049*
H431.30520.38570.23530.043*
H451.03490.19310.21530.044*
H461.21530.09880.23140.047*
H51A0.79980.44240.20640.043*
H51B0.82550.45780.10960.043*
H52A0.88660.31350.10200.037*
H52B0.85710.29620.19810.037*
H53A1.05760.41580.17600.045*
H53B1.03400.38870.27080.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0331 (2)0.0354 (2)0.0339 (2)0.00144 (15)0.00938 (15)0.00827 (16)
O110.0448 (7)0.0373 (7)0.0520 (7)0.0031 (5)0.0181 (6)0.0137 (5)
O120.0387 (7)0.0569 (8)0.0331 (6)0.0067 (5)0.0043 (5)0.0092 (5)
O140.0303 (6)0.0417 (7)0.0776 (10)0.0015 (5)0.0093 (6)0.0174 (6)
O240.0280 (6)0.0423 (7)0.0369 (6)0.0026 (4)0.0110 (4)0.0053 (5)
C110.0288 (8)0.0356 (9)0.0285 (8)0.0003 (6)0.0105 (6)0.0014 (6)
C120.0319 (8)0.0343 (9)0.0408 (9)0.0052 (6)0.0101 (7)0.0045 (7)
C130.0225 (8)0.0431 (10)0.0462 (10)0.0017 (6)0.0073 (6)0.0071 (7)
C140.0313 (9)0.0372 (9)0.0401 (9)0.0003 (6)0.0123 (7)0.0082 (7)
C150.0305 (8)0.0397 (9)0.0410 (9)0.0068 (6)0.0107 (6)0.0126 (7)
C160.0256 (8)0.0454 (9)0.0309 (8)0.0031 (6)0.0074 (6)0.0042 (7)
C210.0272 (8)0.0233 (7)0.0349 (8)0.0020 (5)0.0082 (6)0.0036 (6)
C220.0266 (8)0.0335 (8)0.0400 (9)0.0058 (6)0.0075 (6)0.0019 (7)
C230.0294 (8)0.0323 (8)0.0341 (8)0.0063 (6)0.0047 (6)0.0026 (6)
C240.0280 (7)0.0219 (7)0.0354 (8)0.0028 (5)0.0094 (6)0.0014 (6)
C250.0224 (7)0.0323 (8)0.0404 (9)0.0004 (5)0.0079 (6)0.0004 (7)
C260.0264 (8)0.0297 (8)0.0356 (8)0.0012 (5)0.0031 (6)0.0001 (6)
N310.0317 (7)0.0362 (8)0.0413 (8)0.0012 (5)0.0112 (6)0.0044 (6)
C320.0371 (9)0.0350 (9)0.0470 (10)0.0047 (6)0.0111 (7)0.0065 (7)
C330.0321 (8)0.0306 (8)0.0487 (10)0.0007 (6)0.0156 (7)0.0050 (7)
C340.0304 (8)0.0261 (8)0.0323 (8)0.0009 (5)0.0122 (6)0.0037 (6)
C350.0354 (8)0.0306 (8)0.0297 (8)0.0042 (6)0.0102 (6)0.0000 (6)
C360.0336 (8)0.0361 (9)0.0355 (8)0.0076 (6)0.0135 (6)0.0058 (7)
N410.0304 (7)0.0455 (8)0.0363 (8)0.0055 (5)0.0087 (5)0.0001 (6)
C420.0276 (9)0.0489 (11)0.0472 (10)0.0024 (7)0.0108 (7)0.0039 (8)
C430.0299 (8)0.0365 (9)0.0419 (9)0.0048 (6)0.0095 (6)0.0018 (7)
C440.0286 (8)0.0340 (8)0.0275 (8)0.0012 (6)0.0077 (6)0.0024 (6)
C450.0268 (8)0.0354 (9)0.0474 (10)0.0031 (6)0.0087 (7)0.0034 (7)
C460.0361 (9)0.0348 (9)0.0453 (10)0.0003 (6)0.0069 (7)0.0039 (7)
C510.0303 (8)0.0303 (8)0.0467 (10)0.0001 (6)0.0105 (7)0.0020 (7)
C520.0290 (8)0.0295 (8)0.0344 (8)0.0008 (6)0.0107 (6)0.0011 (6)
C530.0310 (8)0.0328 (9)0.0473 (10)0.0008 (6)0.0091 (7)0.0054 (7)
Geometric parameters (Å, º) top
S1—O111.4436 (12)C25—C261.381 (2)
S1—O121.4412 (12)N31—C321.335 (2)
S1—C111.7528 (16)N31—C361.336 (2)
S1—C211.7542 (15)C32—C331.384 (2)
O14—C141.3426 (19)C33—C341.385 (2)
O24—C241.3477 (18)C34—C351.391 (2)
C11—C121.398 (2)C34—C511.502 (2)
C11—C161.384 (2)C35—C361.370 (2)
C12—C131.379 (2)N41—C421.336 (2)
C13—C141.391 (2)N41—C461.335 (2)
C14—C151.396 (2)C42—C431.372 (2)
C15—C161.376 (2)C43—C441.391 (2)
C21—C221.391 (2)C44—C451.387 (2)
C21—C261.390 (2)C44—C531.506 (2)
C22—C231.373 (2)C45—C461.384 (2)
C23—C241.399 (2)C51—C521.520 (2)
C24—C251.392 (2)C52—C531.521 (2)
O11—S1—O12119.04 (7)C23—C24—C25119.36 (14)
O11—S1—C11107.79 (7)C24—C25—C26120.18 (13)
O11—S1—C21108.57 (7)C21—C26—C25119.84 (14)
O12—S1—C11108.29 (7)C32—N31—C36116.90 (13)
O12—S1—C21107.67 (7)N31—C32—C33123.33 (15)
C11—S1—C21104.55 (7)C32—C33—C34119.66 (15)
S1—C11—C12120.06 (12)C33—C34—C35116.66 (14)
S1—C11—C16120.02 (11)C33—C34—C51123.75 (14)
C12—C11—C16119.84 (15)C35—C34—C51119.53 (13)
C11—C12—C13119.70 (14)C34—C35—C36120.05 (14)
C12—C13—C14120.42 (14)N31—C36—C35123.40 (14)
O14—C14—C13123.18 (14)C42—N41—C46116.75 (14)
O14—C14—C15117.23 (14)N41—C42—C43123.69 (14)
C13—C14—C15119.59 (15)C42—C43—C44119.89 (15)
C14—C15—C16119.99 (15)C43—C44—C45116.56 (14)
C11—C16—C15120.45 (14)C45—C44—C53123.45 (13)
S1—C21—C22119.59 (11)C43—C44—C53119.99 (14)
S1—C21—C26119.95 (12)C44—C45—C46119.85 (14)
C22—C21—C26120.39 (14)N41—C46—C45123.25 (15)
C21—C22—C23119.61 (13)C34—C51—C52117.57 (13)
C22—C23—C24120.60 (14)C51—C52—C53109.24 (12)
O24—C24—C25122.88 (13)C44—C53—C52117.08 (13)
O24—C24—C23117.76 (13)
O12—S1—C11—C1628.38 (15)O24—C24—C25—C26178.56 (13)
O11—S1—C11—C16158.40 (12)C23—C24—C25—C261.7 (2)
C21—S1—C11—C1686.20 (13)C24—C25—C26—C210.8 (2)
O12—S1—C11—C12154.85 (13)C22—C21—C26—C250.5 (2)
O11—S1—C11—C1224.83 (15)S1—C21—C26—C25176.44 (11)
C21—S1—C11—C1290.57 (14)C36—N31—C32—C330.4 (2)
C16—C11—C12—C131.5 (2)N31—C32—C33—C340.3 (3)
S1—C11—C12—C13178.32 (12)C32—C33—C34—C351.1 (2)
C11—C12—C13—C140.6 (2)C32—C33—C34—C51176.13 (16)
C12—C13—C14—O14178.89 (16)C33—C34—C35—C361.1 (2)
C12—C13—C14—C151.0 (3)C51—C34—C35—C36176.20 (14)
O14—C14—C15—C16178.27 (15)C32—N31—C36—C350.4 (2)
C13—C14—C15—C161.6 (3)C34—C35—C36—N310.4 (2)
C14—C15—C16—C110.7 (2)C46—N41—C42—C430.0 (3)
C12—C11—C16—C150.9 (2)N41—C42—C43—C441.0 (3)
S1—C11—C16—C15177.70 (12)C42—C43—C44—C451.4 (2)
O12—S1—C21—C2612.27 (14)C42—C43—C44—C53178.35 (15)
O11—S1—C21—C26142.40 (12)C43—C44—C45—C460.9 (2)
C11—S1—C21—C26102.75 (13)C53—C44—C45—C46178.84 (15)
O12—S1—C21—C22170.74 (12)C42—N41—C46—C450.5 (3)
O11—S1—C21—C2240.61 (14)C44—C45—C46—N410.1 (3)
C11—S1—C21—C2274.24 (13)C33—C34—C51—C5228.8 (2)
C26—C21—C22—C231.0 (2)C35—C34—C51—C52154.06 (14)
S1—C21—C22—C23176.02 (12)C34—C51—C52—C53178.32 (14)
C21—C22—C23—C240.1 (2)C45—C44—C53—C5223.4 (2)
C22—C23—C24—O24178.99 (14)C43—C44—C53—C52156.27 (15)
C22—C23—C24—C251.3 (2)C51—C52—C53—C44173.91 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N310.821.842.6514 (19)171
O24—H24···N41i0.821.882.6850 (18)166
C12—H12···O11ii0.932.543.428 (2)160
C26—H26···O120.932.522.903 (2)105
Symmetry codes: (i) x+2, y, z; (ii) x, y, z.
(7) 4,4'-Sulfonyldiphenol-4,4'-trimethylenedipiperidine-water (2/2/1). top
Crystal data top
2(C13H27N2)·2(C12H9O4S)·H2O? #Insert any comments here.
Mr = 939.25Dx = 1.267 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
a = 12.2739 (10) ÅCell parameters from 25 reflections
b = 19.454 (2) Åθ = 9.5–17.5°
c = 20.6251 (13) ŵ = 0.17 mm1
V = 4924.7 (8) Å3T = 294 K
Z = 4Plate, colourless
F(000) = 20240.40 × 0.38 × 0.19 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
5888 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.019
Graphite monochromatorθmax = 25.2°, θmin = 2.1°
θ/2θ scansh = 014
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
k = 023
Tmin = 0.943, Tmax = 0.972l = 2424
9558 measured reflections3 standard reflections every 120 min
8866 independent reflections intensity decay: 2.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103Calculated w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2197P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
8866 reflectionsΔρmax = 0.21 e Å3
595 parametersΔρmin = 0.17 e Å3
2 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (6)
Crystal data top
2(C13H27N2)·2(C12H9O4S)·H2OV = 4924.7 (8) Å3
Mr = 939.25Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.2739 (10) ŵ = 0.17 mm1
b = 19.454 (2) ÅT = 294 K
c = 20.6251 (13) Å0.40 × 0.38 × 0.19 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
5888 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSO in NRCVAX (Gabe et al., 1989)
Rint = 0.019
Tmin = 0.943, Tmax = 0.9723 standard reflections every 120 min
9558 measured reflections intensity decay: 2.2%
8866 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103Δρmax = 0.21 e Å3
S = 1.03Δρmin = 0.17 e Å3
8866 reflectionsAbsolute structure: Flack (1983)
595 parametersAbsolute structure parameter: 0.06 (6)
2 restraints
Special details top

Experimental. ? #Insert any special details here.

Geometry. The following mean-plane details are from the final SHELXL97 calculation

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

0.1032 (0.0174) x + 2.4128 (0.0418) y + 20.4651 (0.0060) z = 5.2240 (0.0129)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12

Rms deviation of fitted atoms = 0.0000

11.4343 (0.0096) x + 6.9693 (0.0385) y - 1.2686 (0.0317) z = 1.4158 (0.0137)

Angle to previous plane (with approximate e.s.d.) = 89.50 (13)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

3.3232 (0.0135) x - 15.7838 (0.0089) y - 10.6852 (0.0071) z = 1.0851 (0.0027)

Angle to previous plane (with approximate e.s.d.) = 89.62 (12)

* -0.0061 (0.0013) S1 * 0.0079 (0.0022) C11 * -0.0021 (0.0022) C12 * 0.0053 (0.0022) C13 * -0.0052 (0.0025) C14 * 0.0031 (0.0021) C15 * 0.0000 (0.0020) C16 * -0.0029 (0.0017) O14

Rms deviation of fitted atoms = 0.0047

11.4343 (0.0096) x + 6.9693 (0.0385) y - 1.2686 (0.0317) z = 1.4158 (0.0137)

Angle to previous plane (with approximate e.s.d.) = 89.62 (12)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

2.0328 (0.0140) x - 14.0266 (0.0082) y + 13.8770 (0.0071) z = 7.1615 (0.0035)

Angle to previous plane (with approximate e.s.d.) = 81.64 (12)

* 0.0235 (0.0014) S1 * -0.0040 (0.0023) C21 * -0.0101 (0.0022) C22 * -0.0126 (0.0023) C23 * -0.0014 (0.0025) C24 * -0.0104 (0.0022) C25 * -0.0112 (0.0021) C26 * 0.0262 (0.0019) O24

Rms deviation of fitted atoms = 0.0148

################################################################

0.1379 (0.0168) x + 3.4946 (0.0388) y - 20.2883 (0.0078) z = 5.1854 (0.0095)

* 0.0000 (0.0000) S2 * 0.0000 (0.0000) O21 * 0.0000 (0.0000) O22

Rms deviation of fitted atoms = 0.0000

- 11.3320 (0.0103) x - 7.3275 (0.0387) y - 1.5599 (0.0312) z = 2.0353 (0.0116)

Angle to previous plane (with approximate e.s.d.) = 89.79 (12)

* 0.0000 (0.0000) S2 * 0.0000 (0.0000) C31 * 0.0000 (0.0000) C41

Rms deviation of fitted atoms = 0.0000

- 3.7652 (0.0140) x + 15.9832 (0.0100) y - 9.9099 (0.0081) z = 6.4458 (0.0032)

Angle to previous plane (with approximate e.s.d.) = 89.42 (12)

* -0.0196 (0.0013) S2 * 0.0142 (0.0023) C31 * 0.0093 (0.0021) C32 * -0.0002 (0.0022) C33 * -0.0018 (0.0025) C34 * 0.0025 (0.0024) C35 * 0.0066 (0.0023) C36 * -0.0111 (0.0019) O34

Rms deviation of fitted atoms = 0.0103

- 11.3320 (0.0103) x - 7.3275 (0.0387) y - 1.5599 (0.0312) z = 2.0353 (0.0116)

Angle to previous plane (with approximate e.s.d.) = 89.42 (12)

* 0.0000 (0.0000) S2 * 0.0000 (0.0000) C31 * 0.0000 (0.0000) C41

Rms deviation of fitted atoms = 0.0000

- 5.0532 (0.0129) x + 10.8877 (0.0113) y + 14.8338 (0.0068) z = 0.2816 (0.0030)

Angle to previous plane (with approximate e.s.d.) = 83.40 (11)

* -0.0346 (0.0013) S2 * 0.0048 (0.0023) C41 * 0.0104 (0.0021) C42 * 0.0232 (0.0021) C43 * 0.0113 (0.0023) C44 * 0.0250 (0.0022) C45 * 0.0099 (0.0023) C46 * -0.0501 (0.0015) O44

Rms deviation of fitted atoms = 0.0256

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.27531 (7)0.19807 (4)0.27723 (3)0.0428 (2)
O110.39129 (18)0.21011 (11)0.27806 (10)0.0586 (6)
O120.2023 (2)0.25561 (9)0.28438 (10)0.0596 (6)
O140.16741 (18)0.05697 (11)0.03495 (9)0.0565 (6)
O240.1737 (2)0.00532 (13)0.48713 (11)0.0685 (7)
C110.2421 (2)0.15683 (14)0.20468 (13)0.0364 (7)
C120.3215 (3)0.11791 (15)0.17283 (13)0.0453 (7)
C130.2968 (3)0.08503 (15)0.11587 (15)0.0480 (8)
C140.1922 (3)0.08812 (14)0.08887 (13)0.0409 (7)
C150.1145 (3)0.12753 (14)0.12217 (13)0.0418 (7)
C160.1382 (2)0.16106 (14)0.17936 (13)0.0389 (7)
C210.2462 (2)0.13902 (14)0.33920 (13)0.0378 (7)
C220.1404 (3)0.13217 (15)0.36118 (13)0.0443 (8)
C230.1170 (3)0.08660 (16)0.41049 (14)0.0496 (8)
C240.1998 (3)0.04747 (15)0.43871 (13)0.0458 (8)
C250.3053 (3)0.05465 (15)0.41536 (13)0.0448 (8)
C260.3280 (3)0.09989 (15)0.36626 (13)0.0418 (7)
S20.27711 (7)0.19832 (4)0.22331 (3)0.0440 (2)
O210.39419 (18)0.20863 (11)0.22233 (9)0.0564 (6)
O220.2095 (2)0.25765 (9)0.21263 (10)0.0614 (6)
O340.16266 (19)0.07174 (13)0.47181 (10)0.0632 (6)
O440.17196 (17)0.01457 (10)0.03228 (8)0.0462 (5)
C310.2431 (2)0.16176 (14)0.29861 (14)0.0376 (7)
C320.3202 (3)0.12321 (14)0.33100 (13)0.0432 (7)
C330.2951 (3)0.09254 (15)0.38903 (14)0.0454 (8)
C340.1921 (3)0.10021 (15)0.41563 (14)0.0442 (8)
C350.1154 (3)0.13890 (16)0.38281 (15)0.0510 (8)
C360.1403 (3)0.16956 (16)0.32433 (14)0.0497 (8)
C410.2454 (2)0.13672 (14)0.16463 (13)0.0384 (7)
C420.1469 (2)0.13835 (15)0.13192 (13)0.0420 (7)
C430.1235 (2)0.08859 (15)0.08654 (14)0.0424 (7)
C440.1968 (2)0.03495 (14)0.07293 (12)0.0372 (7)
C450.2962 (3)0.03531 (15)0.10615 (14)0.0477 (8)
C460.3194 (3)0.08507 (15)0.15161 (14)0.0478 (8)
N510.0012 (2)0.06171 (12)0.20704 (11)0.0545 (7)
C520.0786 (3)0.01648 (16)0.23892 (15)0.0572 (10)
C530.1457 (3)0.05840 (16)0.28533 (15)0.0516 (8)
C540.0781 (2)0.09618 (15)0.33613 (13)0.0436 (7)
C550.0124 (3)0.13589 (14)0.30235 (14)0.0494 (8)
C560.0748 (3)0.09270 (17)0.25382 (16)0.0555 (9)
C570.1501 (3)0.14114 (16)0.37901 (15)0.0543 (9)
C580.0948 (3)0.17584 (17)0.43601 (16)0.0608 (9)
C590.1745 (3)0.21886 (16)0.47515 (14)0.0523 (8)
N610.0841 (2)0.38003 (12)0.60938 (12)0.0496 (7)
C620.0067 (3)0.34366 (16)0.57560 (15)0.0563 (9)
C630.0360 (3)0.30414 (16)0.51834 (14)0.0528 (8)
C640.1274 (3)0.25476 (15)0.53502 (14)0.0469 (8)
C650.2144 (3)0.29273 (16)0.57249 (14)0.0526 (8)
C660.1715 (3)0.33153 (17)0.63008 (15)0.0572 (9)
N710.0132 (2)0.45270 (13)0.28815 (12)0.0592 (7)
C720.0591 (4)0.50063 (19)0.25359 (17)0.0739 (13)
C730.1334 (3)0.46272 (17)0.21021 (16)0.0608 (9)
C740.0745 (3)0.41753 (16)0.16111 (15)0.0544 (9)
C750.0042 (3)0.37162 (18)0.19824 (18)0.0705 (10)
C760.0766 (3)0.4111 (2)0.2419 (2)0.0807 (13)
C770.1535 (3)0.37766 (16)0.11958 (14)0.0583 (9)
C780.1011 (3)0.32636 (18)0.07305 (17)0.0677 (10)
C790.1823 (3)0.28940 (16)0.03086 (14)0.0594 (9)
N810.0933 (3)0.16182 (14)0.13118 (12)0.0607 (8)
C820.0029 (3)0.19326 (16)0.09429 (15)0.0585 (9)
C830.0439 (3)0.25142 (17)0.05200 (15)0.0596 (9)
C840.1372 (3)0.23045 (15)0.00811 (14)0.0496 (8)
C850.2255 (3)0.19450 (17)0.04827 (15)0.0564 (8)
C860.1835 (3)0.13743 (16)0.08988 (17)0.0590 (9)
O90.0152 (2)0.02220 (13)0.05933 (12)0.0636 (7)
H240.22950.00910.50430.103*
H120.39120.11430.19030.054*
H130.35080.06010.09470.058*
H150.04470.13120.10510.050*
H160.08470.18630.20070.047*
H220.08500.15830.34270.053*
H230.04560.08190.42500.060*
H250.36120.02850.43320.054*
H260.39900.10420.35110.050*
H340.21400.05000.48680.095*
H320.38950.11800.31340.052*
H330.34740.06650.41060.054*
H350.04620.14430.40040.061*
H360.08800.19530.30250.060*
H420.09680.17300.14060.050*
H430.05760.09050.06440.051*
H450.34750.00140.09740.057*
H460.38550.08390.17370.057*
H510.03680.03760.17740.065*
H52A0.12550.00500.20700.069*
H52B0.04010.01940.26220.069*
H53A0.18760.09180.26090.062*
H53B0.19680.02830.30720.062*
H540.04380.06150.36390.052*
H55A0.06280.15320.33470.059*
H55B0.01900.17510.28020.059*
H56A0.11440.05680.27630.067*
H56B0.12710.12120.23110.067*
H57A0.20900.11290.39560.065*
H57B0.18250.17650.35210.065*
H58A0.06280.14110.46380.073*
H58B0.03660.20510.42020.073*
H59A0.20530.25360.44680.063*
H59B0.23380.18940.48910.063*
H61A0.11260.41180.58260.060*
H61B0.05750.40200.64440.060*
H62A0.06030.37690.56110.068*
H62B0.04210.31230.60550.068*
H63A0.06210.33650.48610.063*
H63B0.02350.27840.49910.063*
H640.09730.21920.56350.056*
H65A0.26850.25990.58720.063*
H65B0.25050.32480.54360.063*
H66A0.14250.29940.66170.069*
H66B0.23030.35700.65030.069*
H710.05900.47660.31380.071*
H72A0.01570.53260.22840.089*
H72B0.10120.52690.28470.089*
H73A0.17860.49550.18710.073*
H73B0.18110.43410.23630.073*
H740.03170.44750.13260.065*
H75A0.03710.33880.22370.085*
H75B0.04830.34600.16760.085*
H76A0.12320.37960.26550.097*
H76B0.12280.44110.21620.097*
H77A0.19640.41000.09450.070*
H77B0.20310.35300.14780.070*
H78A0.04980.35060.04550.081*
H78B0.06060.29270.09800.081*
H79A0.21420.32240.00120.071*
H79B0.24040.27210.05820.071*
H81A0.11940.19290.15950.073*
H81B0.06710.12610.15420.073*
H82A0.05140.21070.12420.070*
H82B0.03130.15860.06730.070*
H83A0.06770.28890.07960.072*
H83B0.01580.26820.02550.072*
H840.10860.19660.02270.060*
H85A0.28020.17620.01910.068*
H85B0.26070.22830.07580.068*
H86A0.15820.10010.06260.071*
H86B0.24200.12010.11700.071*
H910.058 (3)0.013 (2)0.0217 (16)0.095 (10)*
H920.032 (3)0.0045 (19)0.0453 (19)0.095 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0533 (5)0.0350 (4)0.0401 (4)0.0042 (4)0.0068 (4)0.0002 (3)
O110.0546 (16)0.0626 (14)0.0585 (14)0.0246 (12)0.0104 (12)0.0027 (12)
O120.0861 (18)0.0347 (11)0.0580 (13)0.0075 (11)0.0108 (13)0.0066 (10)
O140.0568 (15)0.0703 (14)0.0425 (12)0.0008 (12)0.0057 (11)0.0138 (11)
O240.0632 (17)0.0840 (17)0.0585 (14)0.0019 (15)0.0008 (13)0.0266 (13)
C110.044 (2)0.0349 (15)0.0305 (15)0.0012 (14)0.0024 (13)0.0069 (13)
C120.0364 (19)0.0537 (18)0.0458 (17)0.0039 (16)0.0050 (15)0.0014 (15)
C130.041 (2)0.0555 (19)0.0473 (18)0.0050 (16)0.0041 (16)0.0071 (15)
C140.045 (2)0.0434 (16)0.0347 (15)0.0015 (15)0.0011 (15)0.0000 (13)
C150.037 (2)0.0501 (17)0.0386 (16)0.0019 (15)0.0037 (14)0.0058 (15)
C160.0361 (18)0.0414 (16)0.0390 (16)0.0060 (15)0.0006 (14)0.0040 (13)
C210.041 (2)0.0408 (16)0.0315 (15)0.0015 (14)0.0032 (13)0.0014 (13)
C220.047 (2)0.0459 (17)0.0398 (16)0.0101 (16)0.0078 (15)0.0018 (14)
C230.039 (2)0.064 (2)0.0453 (18)0.0025 (17)0.0017 (15)0.0018 (17)
C240.053 (2)0.0500 (18)0.0342 (15)0.0028 (16)0.0022 (15)0.0024 (14)
C250.042 (2)0.0524 (18)0.0395 (16)0.0050 (15)0.0096 (15)0.0033 (14)
C260.0403 (19)0.0513 (17)0.0336 (14)0.0006 (16)0.0048 (14)0.0005 (13)
S20.0561 (6)0.0374 (4)0.0384 (4)0.0101 (4)0.0063 (4)0.0011 (4)
O210.0538 (15)0.0675 (15)0.0480 (13)0.0297 (12)0.0044 (11)0.0026 (12)
O220.0981 (19)0.0309 (11)0.0552 (13)0.0049 (12)0.0142 (14)0.0027 (10)
O340.0583 (16)0.0816 (17)0.0498 (13)0.0009 (13)0.0078 (12)0.0133 (12)
O440.0534 (14)0.0454 (11)0.0397 (11)0.0014 (10)0.0089 (10)0.0076 (9)
C310.040 (2)0.0372 (15)0.0352 (16)0.0009 (14)0.0046 (13)0.0028 (14)
C320.0373 (19)0.0500 (18)0.0422 (16)0.0030 (15)0.0018 (14)0.0012 (14)
C330.046 (2)0.0480 (17)0.0421 (17)0.0001 (16)0.0059 (16)0.0027 (14)
C340.049 (2)0.0483 (17)0.0350 (15)0.0079 (16)0.0001 (16)0.0019 (14)
C350.039 (2)0.065 (2)0.0499 (19)0.0093 (17)0.0052 (16)0.0011 (17)
C360.047 (2)0.0557 (19)0.0469 (18)0.0111 (17)0.0075 (16)0.0015 (15)
C410.046 (2)0.0369 (16)0.0325 (15)0.0053 (14)0.0023 (13)0.0019 (13)
C420.037 (2)0.0425 (17)0.0465 (17)0.0033 (14)0.0024 (15)0.0004 (14)
C430.0358 (19)0.0506 (18)0.0409 (17)0.0014 (15)0.0062 (14)0.0009 (15)
C440.0406 (19)0.0397 (16)0.0315 (14)0.0071 (14)0.0019 (13)0.0032 (12)
C450.045 (2)0.0457 (17)0.0528 (18)0.0076 (15)0.0043 (16)0.0012 (14)
C460.0405 (19)0.056 (2)0.0470 (17)0.0026 (16)0.0129 (16)0.0020 (15)
N510.066 (2)0.0460 (14)0.0518 (15)0.0097 (15)0.0123 (14)0.0032 (12)
C520.071 (3)0.0428 (18)0.058 (2)0.0011 (18)0.0022 (19)0.0070 (16)
C530.046 (2)0.0519 (17)0.0564 (19)0.0085 (16)0.0006 (16)0.0069 (16)
C540.0445 (19)0.0422 (16)0.0441 (16)0.0010 (15)0.0041 (15)0.0028 (14)
C550.046 (2)0.0443 (16)0.0582 (18)0.0022 (15)0.0022 (16)0.0002 (14)
C560.041 (2)0.055 (2)0.071 (2)0.0044 (18)0.0064 (17)0.0099 (18)
C570.053 (2)0.0535 (19)0.0560 (19)0.0044 (17)0.0001 (17)0.0022 (16)
C580.064 (2)0.060 (2)0.059 (2)0.0111 (18)0.0044 (18)0.0080 (16)
C590.054 (2)0.0536 (19)0.0492 (18)0.0008 (17)0.0046 (17)0.0036 (15)
N610.0531 (18)0.0459 (15)0.0498 (15)0.0001 (13)0.0034 (13)0.0020 (12)
C620.048 (2)0.0551 (19)0.066 (2)0.0022 (17)0.0121 (17)0.0024 (17)
C630.054 (2)0.0531 (18)0.0517 (17)0.0030 (18)0.0126 (16)0.0005 (16)
C640.060 (2)0.0400 (16)0.0409 (16)0.0055 (16)0.0021 (16)0.0077 (13)
C650.050 (2)0.0542 (19)0.0539 (18)0.0103 (17)0.0132 (16)0.0054 (16)
C660.054 (2)0.060 (2)0.058 (2)0.0104 (18)0.0146 (17)0.0011 (17)
N710.064 (2)0.0603 (16)0.0537 (16)0.0011 (15)0.0090 (15)0.0080 (13)
C720.096 (4)0.059 (2)0.067 (2)0.008 (2)0.004 (2)0.0018 (19)
C730.065 (2)0.0525 (19)0.065 (2)0.0159 (18)0.0055 (19)0.0050 (17)
C740.058 (2)0.0506 (19)0.0543 (19)0.0060 (17)0.0040 (17)0.0022 (16)
C750.056 (2)0.065 (2)0.090 (3)0.012 (2)0.003 (2)0.022 (2)
C760.063 (3)0.079 (3)0.100 (3)0.003 (2)0.011 (2)0.014 (2)
C770.071 (3)0.059 (2)0.0446 (17)0.0059 (19)0.0023 (17)0.0038 (16)
C780.074 (3)0.069 (2)0.060 (2)0.005 (2)0.013 (2)0.0151 (18)
C790.075 (3)0.059 (2)0.0444 (17)0.0036 (19)0.0034 (18)0.0025 (16)
N810.090 (2)0.0503 (16)0.0419 (15)0.0134 (16)0.0039 (15)0.0059 (13)
C820.063 (2)0.0523 (18)0.0596 (19)0.0058 (19)0.0120 (18)0.0031 (17)
C830.076 (3)0.0559 (19)0.0472 (18)0.0020 (19)0.0121 (18)0.0027 (15)
C840.061 (2)0.0453 (18)0.0428 (17)0.0014 (16)0.0031 (16)0.0034 (14)
C850.061 (2)0.0568 (19)0.0518 (18)0.0027 (19)0.0062 (17)0.0014 (16)
C860.054 (2)0.056 (2)0.067 (2)0.0025 (18)0.0023 (19)0.0017 (17)
O90.0613 (17)0.0634 (15)0.0659 (15)0.0018 (14)0.0165 (13)0.0049 (12)
Geometric parameters (Å, º) top
S1—O111.443 (2)C44—C451.400 (4)
S1—O121.441 (2)C45—C461.378 (4)
S1—C111.746 (3)N51—C521.453 (4)
S1—C211.755 (3)N51—C561.471 (4)
O14—C141.302 (3)C52—C531.503 (4)
O24—C241.331 (3)C53—C541.525 (4)
C11—C121.398 (4)C54—C551.522 (4)
C11—C161.380 (4)C54—C571.526 (4)
C12—C131.371 (4)C55—C561.514 (4)
C13—C141.402 (4)C57—C581.516 (4)
C14—C151.402 (4)C58—C591.520 (4)
C15—C161.379 (4)C59—C641.532 (4)
C21—C221.382 (4)N61—C621.492 (4)
C21—C261.378 (4)N61—C661.491 (4)
C22—C231.379 (4)C62—C631.503 (4)
C23—C241.397 (4)C63—C641.516 (4)
C24—C251.388 (4)C64—C651.511 (4)
C25—C261.370 (4)C65—C661.503 (4)
S2—O211.451 (2)N71—C721.472 (4)
S2—O221.438 (2)N71—C761.474 (4)
S2—C311.758 (3)C72—C731.476 (5)
S2—C411.747 (3)C73—C741.524 (4)
O34—C341.334 (3)C74—C771.508 (4)
O44—C441.313 (3)C74—C751.522 (4)
C31—C321.380 (4)C75—C761.480 (5)
C31—C361.377 (4)C77—C781.526 (4)
C32—C331.372 (4)C78—C791.505 (5)
C33—C341.386 (4)C79—C841.506 (4)
C34—C351.383 (4)N81—C821.477 (4)
C35—C361.380 (4)N81—C861.476 (4)
C41—C421.384 (4)C82—C831.514 (4)
C41—C461.381 (4)C83—C841.516 (4)
C42—C431.377 (4)C84—C851.532 (4)
C43—C441.406 (4)C85—C861.495 (4)
O11—S1—O12119.08 (14)C41—C42—C43119.8 (3)
O11—S1—C11108.36 (14)C42—C43—C44121.6 (3)
O11—S1—C21107.36 (14)C43—C44—C45117.2 (3)
O12—S1—C11107.43 (13)O44—C44—C43121.6 (3)
O12—S1—C21107.89 (14)O44—C44—C45121.2 (3)
C11—S1—C21106.01 (13)C44—C45—C46121.1 (3)
S1—C11—C12119.3 (2)C41—C46—C45120.5 (3)
S1—C11—C16120.8 (2)C52—N51—C56111.5 (2)
C12—C11—C16119.9 (3)N51—C52—C53108.6 (3)
C11—C12—C13120.1 (3)C52—C53—C54113.6 (3)
C12—C13—C14121.5 (3)C53—C54—C55109.1 (2)
C13—C14—C15116.8 (3)C53—C54—C57111.0 (3)
O14—C14—C13122.2 (3)C55—C54—C57113.4 (2)
O14—C14—C15120.9 (3)C54—C55—C56112.9 (2)
C14—C15—C16122.3 (3)N51—C56—C55109.9 (3)
C11—C16—C15119.4 (3)C54—C57—C58116.5 (3)
S1—C21—C22119.6 (2)C57—C58—C59111.7 (3)
S1—C21—C26120.6 (2)C58—C59—C64115.8 (3)
C22—C21—C26119.9 (3)C62—N61—C66111.8 (2)
C21—C22—C23120.0 (3)N61—C62—C63110.4 (3)
C22—C23—C24120.4 (3)C62—C63—C64113.8 (2)
O24—C24—C23118.2 (3)C59—C64—C63112.7 (2)
O24—C24—C25123.1 (3)C59—C64—C65111.6 (3)
C23—C24—C25118.6 (3)C63—C64—C65109.2 (2)
C24—C25—C26120.7 (3)C64—C65—C66113.7 (3)
C21—C26—C25120.4 (3)N61—C66—C65110.1 (2)
O21—S2—O22117.27 (15)C72—N71—C76110.6 (3)
O21—S2—C31107.65 (13)N71—C72—C73110.5 (3)
O21—S2—C41107.82 (14)C72—C73—C74113.4 (3)
O22—S2—C31108.84 (14)C73—C74—C75107.8 (3)
O22—S2—C41108.40 (13)C73—C74—C77111.7 (3)
C31—S2—C41106.35 (13)C75—C74—C77113.1 (3)
S2—C31—C32119.0 (2)C74—C75—C76112.5 (3)
S2—C31—C36120.9 (2)N71—C76—C75111.2 (3)
C32—C31—C36120.1 (3)C74—C77—C78115.0 (3)
C31—C32—C33120.3 (3)C77—C78—C79113.4 (3)
C32—C33—C34120.2 (3)C78—C79—C84115.4 (3)
C33—C34—C35119.1 (3)C82—N81—C86113.5 (2)
O34—C34—C35117.8 (3)N81—C82—C83110.9 (3)
O34—C34—C33123.1 (3)C82—C83—C84113.2 (3)
C34—C35—C36120.8 (3)C79—C84—C83113.0 (3)
C31—C36—C35119.5 (3)C79—C84—C85112.1 (3)
S2—C41—C42121.1 (2)C83—C84—C85109.5 (3)
S2—C41—C46119.1 (2)C84—C85—C86114.0 (3)
C42—C41—C46119.8 (3)N81—C86—C85110.6 (3)
O12—S1—C11—C1626.2 (3)C46—C41—C42—C430.1 (4)
O11—S1—C11—C16156.1 (2)S2—C41—C42—C43179.1 (2)
C21—S1—C11—C1689.0 (2)C41—C42—C43—C440.9 (4)
O12—S1—C11—C12155.2 (2)C42—C43—C44—O44176.2 (3)
O11—S1—C11—C1225.3 (3)C42—C43—C44—C451.8 (4)
C21—S1—C11—C1289.6 (2)O44—C44—C45—C46176.1 (3)
C16—C11—C12—C131.2 (4)C43—C44—C45—C461.9 (4)
S1—C11—C12—C13179.8 (2)C44—C45—C46—C411.2 (5)
C11—C12—C13—C141.3 (5)C42—C41—C46—C450.2 (4)
C12—C13—C14—O14179.8 (3)S2—C41—C46—C45179.2 (2)
C12—C13—C14—C151.2 (4)C56—N51—C52—C5362.4 (3)
O14—C14—C15—C16180.0 (3)N51—C52—C53—C5457.7 (4)
C13—C14—C15—C161.0 (4)C52—C53—C54—C5550.8 (3)
C14—C15—C16—C110.9 (4)C52—C53—C54—C57176.5 (3)
C12—C11—C16—C151.0 (4)C53—C54—C55—C5648.7 (3)
S1—C11—C16—C15179.6 (2)C57—C54—C55—C56173.1 (3)
O12—S1—C21—C26146.6 (2)C52—N51—C56—C5561.4 (3)
O11—S1—C21—C2617.1 (3)C54—C55—C56—N5154.5 (3)
C11—S1—C21—C2698.5 (2)C55—C54—C57—C5862.9 (4)
O12—S1—C21—C2233.0 (3)C53—C54—C57—C58173.9 (3)
O11—S1—C21—C22162.5 (2)C54—C57—C58—C59179.8 (3)
C11—S1—C21—C2281.9 (3)C57—C58—C59—C64178.5 (3)
C26—C21—C22—C230.5 (4)C66—N61—C62—C6356.6 (3)
S1—C21—C22—C23179.1 (2)N61—C62—C63—C6454.5 (3)
C21—C22—C23—C240.4 (4)C62—C63—C64—C6551.5 (4)
C22—C23—C24—O24178.5 (3)C62—C63—C64—C59176.1 (3)
C22—C23—C24—C251.1 (4)C58—C59—C64—C65176.8 (3)
O24—C24—C25—C26178.6 (3)C58—C59—C64—C6359.9 (4)
C23—C24—C25—C260.9 (4)C63—C64—C65—C6652.1 (3)
C24—C25—C26—C210.0 (4)C59—C64—C65—C66177.4 (2)
C22—C21—C26—C250.7 (4)C62—N61—C66—C6557.1 (3)
S1—C21—C26—C25178.9 (2)C64—C65—C66—N6155.7 (4)
O22—S2—C31—C3627.0 (3)C76—N71—C72—C7358.0 (4)
O21—S2—C31—C36155.1 (2)N71—C72—C73—C7456.9 (4)
C41—S2—C31—C3689.6 (3)C72—C73—C74—C77177.8 (3)
O22—S2—C31—C32154.8 (2)C72—C73—C74—C7553.0 (4)
O21—S2—C31—C3226.8 (3)C77—C74—C75—C76176.5 (3)
C41—S2—C31—C3288.6 (2)C73—C74—C75—C7652.5 (4)
C36—C31—C32—C330.1 (4)C72—N71—C76—C7558.5 (4)
S2—C31—C32—C33178.3 (2)C74—C75—C76—N7157.0 (4)
C31—C32—C33—C340.1 (4)C75—C74—C77—C7853.1 (4)
C32—C33—C34—O34180.0 (3)C73—C74—C77—C78174.9 (3)
C32—C33—C34—C350.2 (5)C74—C77—C78—C79178.0 (3)
O34—C34—C35—C36179.7 (3)C77—C78—C79—C84170.6 (3)
C33—C34—C35—C360.1 (5)C86—N81—C82—C8355.6 (3)
C32—C31—C36—C350.4 (4)N81—C82—C83—C8453.4 (4)
S2—C31—C36—C35178.5 (2)C78—C79—C84—C8357.1 (4)
C34—C35—C36—C310.4 (5)C78—C79—C84—C85178.5 (3)
O22—S2—C41—C46160.2 (2)C82—C83—C84—C79176.5 (3)
O21—S2—C41—C4632.3 (3)C82—C83—C84—C8550.7 (4)
C31—S2—C41—C4682.9 (3)C79—C84—C85—C86177.6 (3)
O22—S2—C41—C4220.8 (3)C83—C84—C85—C8651.3 (4)
O21—S2—C41—C42148.7 (2)C82—N81—C86—C8555.6 (4)
C31—S2—C41—C4296.1 (3)C84—C85—C86—N8153.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H91···O440.951.87 (4)2.790 (3)162 (3)
O9—H92···O140.831.96 (4)2.766 (3)163 (4)
O24—H24···O14i0.821.692.499 (3)167
O34—H34···O44ii0.821.822.629 (3)169
N51—H51···O90.902.473.148 (3)133
N61—H61A···O44iii0.901.912.810 (3)175
N61—H61B···N71iv0.901.912.809 (3)173
N81—H81B···N510.901.852.742 (4)172
N81—H81A···O21v0.902.323.148 (3)153
N81—H81A···O22v0.902.563.337 (4)145
C12—H12···O110.932.602.943 (4)102
C13—H13···O24vi0.932.583.205 (4)125
C26—H26···O110.932.552.917 (4)104
C32—H32···O210.932.582.934 (3)103
C33—H33···O9ii0.932.493.397 (4)164
C56—H56B···O12iii0.972.593.432 (4)146
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x1/2, y, z1/2; (iii) x, y+1/2, z+1/2; (iv) x, y, z+1; (v) x+1/2, y+1/2, z; (vi) x+1/2, y, z1/2.

Experimental details

(5)(6a)(6b)(6c)
Crystal data
Chemical formula2(C12H10O4S)·C4H4N2C12H10O4S·C10H8N2C12H10O4S·C12H10N2C12H10O4S·C12H12N2
Mr580.64406.44432.48434.50
Crystal system, space groupMonoclinic, P21/aMonoclinic, P21/nTriclinic, P1Triclinic, P1
Temperature (K)294294294294
a, b, c (Å)8.3506 (9), 18.0102 (17), 9.6360 (14)7.5765 (10), 23.9154 (10), 11.225 (2)7.3981 (8), 12.7472 (15), 13.0006 (13)7.7599 (9), 12.4866 (16), 12.914 (2)
α, β, γ (°)90, 110.869 (8), 9090, 105.921 (10), 90115.037 (8), 102.398 (10), 94.239 (10)114.003 (14), 104.694 (14), 93.690 (13)
V3)1354.1 (3)1955.9 (4)1065.9 (2)1085.7 (3)
Z2422
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.250.200.190.18
Crystal size (mm)0.42 × 0.35 × 0.250.42 × 0.22 × 0.180.42 × 0.28 × 0.240.42 × 0.42 × 0.32
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correctionGaussian
ABSO in NRCVAX (Gabe et al., 1989)
Gaussian
ABSO in NRCVAX96 (Gabe et al., 1989)
Gaussian
ABSO in NRCVAX (Gabe et al., 1989)
Gaussian
ABSO in NRCVAX (Gabe et al., 1989)
Tmin, Tmax0.915, 0.9510.952, 0.9710.949, 0.9670.934, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
3271, 3102, 2431 3774, 3504, 2461 3829, 3829, 2948 4973, 4973, 3905
Rint0.0080.0110.0000.000
(sin θ/λ)max1)0.6480.5970.5990.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.04 0.039, 0.098, 1.05 0.036, 0.100, 0.98 0.042, 0.123, 1.07
No. of reflections3102350438294973
No. of parameters183265330283
No. of restraints00410
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.220.23, 0.250.21, 0.200.43, 0.32
Absolute structure????
Absolute structure parameter????


(6d)(7)
Crystal data
Chemical formulaC12H10O4S·C13H14N22(C13H27N2)·2(C12H9O4S)·H2O
Mr448.52939.25
Crystal system, space groupMonoclinic, P21/cOrthorhombic, P212121
Temperature (K)150294
a, b, c (Å)10.0292 (10), 15.579 (2), 15.0208 (10)12.2739 (10), 19.454 (2), 20.6251 (13)
α, β, γ (°)90, 105.4699 (10), 9090, 90, 90
V3)2261.9 (4)4924.7 (8)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.180.17
Crystal size (mm)0.30 × 0.30 × 0.300.40 × 0.38 × 0.19
Data collection
DiffractometerEnraf-Nonius KappaCCD
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correctionGaussian
ABSO in NRCVAX (Gabe et al., 1989)
Tmin, Tmax0.943, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
10602, 5465, 3828 9558, 8866, 5888
Rint0.0310.019
(sin θ/λ)max1)0.7080.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.04 0.042, 0.103, 1.03
No. of reflections54658866
No. of parameters292595
No. of restraints02
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.360.21, 0.17
Absolute structure?Flack (1983)
Absolute structure parameter?0.06 (6)

Computer programs: CAD4 (Enraf-Nonius, 1992), KappaCCD (Enraf-Nonius, 1997), SET4 & CELDIM (Enraf-Nonius, 1992), DENZO (Enraf-Nonius, 1997), DATRD2 in NRCVAX96 (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997a), SHELXS97 (Sheldrick, 1997), NRCVAX96 and SHELXL97 (Sheldrick, 1997b), NRCVAX96 and SHELXL97 (Sheldrick, 1997), NRCVAX96 (Gabe et al., 1989) and SHELXL97 (Sheldrick, 1997b), NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998), NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997), NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

Hydrogen-bond geometry (Å, º) for (5) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O24i0.932.463.353 (2)161
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) for (6c) top
D—H···AD—HH···AD···AD—H···A
C46—H46···O14i0.932.573.476 (3)164
Symmetry code: (i) x1, y, z1.
Hydrogen-bond geometry (Å, º) for (7) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O9i0.932.493.397 (4)164
Symmetry code: (i) x1/2, y, z1/2.
Symmetry code: (i) 1-x,1-y,1-z. top
(5)
O14—C141.354 (2)O24—C241.3548 (18)
N1—C21.329 (2)N1—C61.323 (2)
C2—C6i1.372 (3)
O11—S1—C11—C1222.0 (2)O11—S1—C21—C22-19.5 (2)
(6a)
O14—C141.349 (2)O24—C241.351 (3)
C33—C341.378 (3)
O12—S1—C11—C163.4 (2)O11—S1—C21—C22-24.8 (2)
Interplanar angle (N31,—C32-C36,C44)(N41,C42–C46,C34)24.4 (1)
(6b)
O14—C141.349 (2)O24—C241.344 (2)
C34—C371.457 (3)C54—C571.456 (5)
C37—C471.308 (3)C57—C671.303 (5)
C44—C471.464 (3)C64—C671.464 (5)
O11—S1—C21—C22-0.85 (18)O12—S1—C11—C1610.68 (17)
C33—C34—C37—C47179.8 (4)C53—C54—C57—C67174.3 (12)
C43—C44—C47—C37176.4 (3)C63—C64—C67—C57169.4 (10)
(6c)
O14—C141.3528 (19)O24—C241.347 (2)
C34—C371.512 (2)C44—C471.515 (2)
C37—C471.474 (3)
O12—S1—C11—C164.25 (16)O11—S1—C21—C22-2.71 (17)
C33—C34—C37—C47101.9 (3)C43—C44—C47—C37-126.6 (2)
C35—C34—C37—C47-79.2 (3)C45—C44—C47—C3753.9 (3)
C34—C37—C47—C44179.7 (2)
(6d)
O14—C141.3426 (19)O24—C241.3477 (18)
C34—C511.502 (2)C44—C531.506 (2)
C51—C521.520 (2)C52—C531.521 (2)
O11—S1—C11—C12-24.83 (15)O12—S1—C21—C26-12.27 (14)
C33—C34—C51—C52-28.8 (2)C45—C44—C53—C52-23.4 (2)
C34—C51—C52—C53-178.32 (14)C51—C52—C53—C44-173.91 (14)
(7)
O14—C141.302 (3)O34—C341.334 (3)
O24—C241.331 (3)O44—C441.313 (3)
N51—C521.453 (4)N71—C721.472 (4)
N51—C561.471 (4)N71—C761.474 (4)
N61—C621.492 (4)N81—C821.477 (4)
N61—C661.491 (4)N81—C861.476 (4)
O11—S1—C11—C12-25.3 (3)O21—S2—C31—C32-26.8 (3)
O11—S1—C21—C2617.1 (3)O21—S2—C41—C4632.3 (3)
C54—C57—C58—C59179.8 (3)C74—C77—C78—C79-178.0 (3)
C57—C58—C59—C64-178.5 (3)C77—C78—C79—C84-170.6 (3)
C53—C54—C57—C58-173.9 (3)C73—C74—C77—C78-174.9 (3)
C55—C54—C57—C5862.9 (4)C75—C74—C77—C78-53.1 (4)
C58—C59—C64—C63-59.9 (4)C78—C79—C84—C83-57.1 (4)
C58—C59—C64—C65176.8 (3)C78—C79—C84—C85178.5 (3)
Hydrogen-Bond distances (Å,°) top
(5)
O14···N12.792 (2)O14—H14···N1167
O24···O12i2.732 (2)O24—H24···O12i174
C13···O24ii3.353 (2)C13—H13···O24ii161
(6a)
O14···N312.721 (3)O14—H14···N31167
O24···N41iii2.731 (3)O24—H24···N41iii176
C12···O12iv3.376 (3)C12—H12···O12iv165
C42···O14ii3.487 (3)C42—H42···O14ii167
(6b)
O14···N312.743 (4)O14—H14···N31171
O14···N51v2.730 (7)O14—H14···N51v172
O24···N412.688 (5)O24—H24···N41173
O24···N61v2.714 (7)O24—H24···N61v174
(6c)
O14···N312.735 (2)O14—H14···N31170
O24···N41v2.706 (2)O24—H24···N41v174
C46···O14vi3.476 (3)C46—H46···O14vi164
(6d)
O14···N312.6514 (19)O14—H14···N31171
O24···N41vii2.6850 (18)O24—H24···N41vii166
C12···O11viii3.428 (2)C12—H12···O11viii160
(7)
O9···O442.790 (3)O9—H91···O44162 (3)
O9···O142.766 (3)O9—H92···O14163 (4)
O24···O14ix2.499 (3)O24—H24···O14ix167
O34···O44x2.629 (3)O24—H24···O44x169
N51···O93.148 (3)N51—H51···O9133
N61···N71xi2.809 (3)N61—H61B···N7xi173
N61···O44xii2.810 (3)N61—H61A···O44xii175
N81···N512.742 (4)N81—H81B···N51172
N81···O21xiii3.148 (3)N81—H81A···O21xiii153*
N81···O22xiii3.337 (4)N81—H81A···O22xiii145*
C33···O93.397 (4)C33—H33···O9164
*Angle O21xiii···H81A···O22xiii is 61°; sum of angles at H81A is 359°. Symmetry codes: (i) x-1,y,z; (ii) 1+x,y,1+z (iii) 3/2-x,1/2+y,3/2-z; (iv) 1/2+x, 1/2-y, 1/2+z; (v) 1+x,1+y,2+z; (vi) x-1,y,z-1 (vii) 2+x,y,z; (viii) -x,-y,-z. (ix) 1/2-x,-y,1/2+z; (x) -1/2-x,-y,z-1/2; (xi) x,y,1+z; (xii) -x,1/2=y,1/2-z; (xiii) 1/2+x,1/2-y,-z.
 
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