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The crystal structure of the title compound, C26H18N4O6S, determined from synchrotron data with a small crystal, is characterized by the presence of whole-mol­ecule disorder. In each mol­ecule, the two planar portions are approximately perpendicular to one another and there are short intermolecular contacts between the nitro groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103025149/bm1545sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103025149/bm1545IIsup2.hkl
Contains datablock II

CCDC reference: 229114

Comment top

Dapsone (4-aminophenylsulfone), (I), is an antibiotic that is used with other drugs to treat leprosy. It is also used to help control dermatitis herpetiformis and to prevent pneumocystis carinii pneumonia in people infected with HIV (British National Formulary 45, 2003). The crystal form of (I) has been reported at room temperature by various authors (e.g., Dickinson et al., 1970; Bocelli & Cantoni, 1990; Bertolasi et al., 1993).

4,4'-Sulfonylbis[N-(4-nitrophenylmethylene)benzenamine], (II), has been synthesized from dapsone, and the unusual crystal structure of (II) is now reported. The molecules in the crystal are disordered such that each atom occupies two sites. A plot of a resolved single molecule is shown in Fig.1, and the two overlapping molecules are shown in Fig.2. There is a very small separation between the coordinates for each of the atom pairs but atom positions for the two molecules are resolved.

Essentially, the molecule consists of two planar portions that are inclined to one another by 87.6 (1)° for the minor conformer [population parameter 0.430 (5)] and 87.8 (1)° for the major conformer [population parameter 0.570 (5)]. The disorder prevents a discussion of accurate molecular geometry, but values are similar to those found in other diphenyl sulfones (Sime & Woodhouse, 1974a; Sime & Woodhouse, 1974b; Bertolasi et al., 1993; Glidewell et al., 2001). There are close intermolecular interactions between the O and N atoms of the nitro groups, as shown in Table 2 (Platts et al., 1995) and Fig. 3. While close O···N separations have been observed previously, such as in 1-chloro-3-nitrobenzene (Sharma et al., 1985) and (4,5-spirobi(adamantyl)-N-(3,5- dinitrophenyl)-1,3,2-dioxazolidine (Okada et al., 1992), the close O···O separations in the absence of hydrogen bonding are unusual. The N—O bond lengths indicate that the negative charge distribution between the two O atoms in each nitro group may be unequal. The sixteen O—N—Car—Car torsion angles range from 21.5 (13) to −159.2 (7)° and indicate that some of the nitro groups are twisted slightly from the planes of the aromatic rings. There is some evidence that the molecules A are held together by C—H···O bonding, but the disorder prevents an accurate description of the geometries involved.

The percentage of disordered organic structures in the Cambridge Structural Database (Allen, 2002) rose from 3.9% in 1970 to 15.0% in 1999 (Flippen-Anderson et al., 2001). The April 2003 release of the database contains 49743 structures with some form of disorder out of a total of 296427, i.e. 16.8%. Although whole-molecule disorder is unusual, two crystal structures that exhibit this phenomenon, 2-(2-thienyl)-1-(pyrazinyl)ethene and 2-(2-thienyl)-1-(quinoxalinyl)ethene, have been reported (Ichharam et al., 2001).

Experimental top

To a solution of dapsone (1 mmol) in methanol (30 ml) was added a solution of 4-nitrobenzaldehyde (2 mmol) in methanol (10 ml). The mixture was refluxed for 3 h and then cooled, and all the volatiles were removed under vacuum. The resulting solid was recrystallized from toluene. IR (KBr disc, cm−1): ν 3099, 3079, 3061, 2998, 2946, 2885, 1627, 1602, 1579, 1541, 1491, 1412, 1350, 1324, 1296, 1282, 1185, 1151, 1105, 1071, 1005, 954, 854, 748, 735, 706, 683, 663, 642, 633, 584, 560, 503. M.p. 504–506 K. A data set was collected with synchrotron radiation at the Daresbury synchrotron radiation source, station 9.8 (Cernik et al., 1997; Clegg et al., 1998).

Refinement top

Following structure elucidation, refinement was impeded by non-positive definite anisotropic displacement parameters for several atoms. Because of the disorder, all atoms were refined in SHELXL97 with isotropic displacement parameters. The Car—Car bond lengths were restrained to 1.395 Å before each refinement cycle. Atom population parameters of the two molecules were refined and converged to 0.430 (5) and 0.570 (5). The H atoms were initially placed in calculated positions (C—H = 0.95 Å) and thereafter were allowed to ride on their attached atoms with a common isotropic displacement parameter, which refined to 0.026 (2) Å2. The N—O bonds range from 1.103 (11) to 1.362 (17) Å.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97-2 (Sheldrick, 1998); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The atomic arrangement in the molecule of (II) (disorder excluded). Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. The atomic arrangement in the molecule of(II) (disorder included). Displacement ellipsoids are shown at the 50% probability level.
[Figure 3] Fig. 3. A view of the crystal packing.
(II) top
Crystal data top
C26H18N4O6SF(000) = 1064
Mr = 514.5Dx = 1.551 Mg m3
Monoclinic, CcSynchrotron radiation, λ = 0.6934 Å
Hall symbol: C -2ycCell parameters from 1948 reflections
a = 36.706 (3) Åθ = 3.3–25.2°
b = 4.9130 (4) ŵ = 0.20 mm1
c = 12.364 (5) ÅT = 120 K
β = 98.808 (4)°Lozenge, yellow
V = 2203.4 (9) Å30.15 × 0.05 × 0.02 mm
Z = 4
Data collection top
Bruker SMART 1K CCD
diffractometer
3069 reflections with I > 2σ(I)
ω rotation with narrow frames scansRint = 0.036
Absorption correction: multi-scan
SADABS (Bruker, 2000)
θmax = 25.7°, θmin = 3.3°
Tmin = 0.970, Tmax = 0.996h = 4545
9138 measured reflectionsk = 56
4141 independent reflectionsl = 1515
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0612P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042(Δ/σ)max = 0.002
wR(F2) = 0.107Δρmax = 0.22 e Å3
S = 1.01Δρmin = 0.44 e Å3
4141 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
299 parametersAbsolute structure parameter: 0.3 (2)
50 restraints
Crystal data top
C26H18N4O6SV = 2203.4 (9) Å3
Mr = 514.5Z = 4
Monoclinic, CcSynchrotron radiation, λ = 0.6934 Å
a = 36.706 (3) ŵ = 0.20 mm1
b = 4.9130 (4) ÅT = 120 K
c = 12.364 (5) Å0.15 × 0.05 × 0.02 mm
β = 98.808 (4)°
Data collection top
Bruker SMART 1K CCD
diffractometer
4141 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2000)
3069 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.996Rint = 0.036
9138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.107Δρmax = 0.22 e Å3
S = 1.01Δρmin = 0.44 e Å3
4141 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
299 parametersAbsolute structure parameter: 0.3 (2)
50 restraints
Special details top

Experimental. When there are two overlapping images then the expectation is: a normal (i.e., not racemic) twin, or the wrong space group, or the data have been collected with one axis halved. Data from Professor W. Clegg who commented: the space group is, of course, an ambiguous one, and there may be some pseudo symmetry in this structure, so it does not look trivial.

Advice from Simon Parsons taken regarding possible twinning: Clearly a tricky one, I can't see anything that I'd have done differently. There is a possible twin operation about [100], but when I introduce this (with or without the disorder) its scale refines to zero. So I think this is fine as it is.

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

Refinement. Cc was the only space group that led to a structure solution with Sir97, no sensible solution was found for C2/c

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.48835 (5)1.1073 (4)0.36781 (17)0.0009 (6)*0.430 (5)
O10.50208 (17)1.2633 (12)0.2846 (5)0.0099 (16)*0.430 (5)
O20.47342 (18)1.2564 (13)0.4571 (5)0.0057 (14)*0.430 (5)
O30.7442 (2)0.6570 (15)0.6995 (5)0.0095 (15)*0.430 (5)
O40.71713 (18)0.7175 (16)0.8458 (6)0.0067 (13)*0.430 (5)
O50.2705 (3)0.6895 (14)0.1624 (5)0.0137 (16)*0.430 (5)
O60.2450 (2)0.7028 (19)0.0127 (8)0.018 (2)*0.430 (5)
N10.5990 (3)0.3283 (18)0.5931 (7)0.0088 (19)*0.430 (5)
N20.7188 (4)0.624 (2)0.7616 (11)0.001 (3)*0.430 (5)
N30.3747 (2)0.3041 (19)0.1892 (7)0.0087 (18)*0.430 (5)
N40.2690 (3)0.623 (2)0.0780 (7)0.019 (3)*0.430 (5)
C10.5230 (3)0.889 (2)0.4347 (7)0.010 (2)*0.430 (5)
C20.5210 (2)0.7959 (18)0.5387 (7)0.010 (2)*0.430 (5)
H20.50120.84940.57520.0258 (18)*0.430 (5)
C30.5481 (2)0.6235 (17)0.5895 (7)0.014 (2)*0.430 (5)
H30.54830.57690.66410.0258 (18)*0.430 (5)
C40.5753 (2)0.5163 (18)0.5343 (7)0.006 (2)*0.430 (5)
C50.5785 (2)0.6291 (17)0.4314 (6)0.011 (2)*0.430 (5)
H50.59900.58230.39660.0258 (18)*0.430 (5)
C60.5517 (2)0.8104 (19)0.3799 (8)0.010 (2)*0.430 (5)
H60.55310.87800.30870.0258 (18)*0.430 (5)
C70.6211 (3)0.174 (2)0.5431 (9)0.010 (2)*0.430 (5)
H70.62010.19160.46620.0258 (18)*0.430 (5)
C80.6465 (3)0.0207 (19)0.6012 (8)0.005 (2)*0.430 (5)
C90.6447 (3)0.083 (2)0.7099 (9)0.015 (3)*0.430 (5)
H90.62780.01870.74470.0258 (18)*0.430 (5)
C100.6654 (3)0.279 (2)0.7722 (12)0.020 (4)*0.430 (5)
H100.66200.32570.84450.0258 (18)*0.430 (5)
C110.6912 (5)0.400 (4)0.7194 (12)0.016 (5)*0.430 (5)
C120.6930 (5)0.339 (3)0.6107 (13)0.033 (5)*0.430 (5)
H120.71130.43140.57790.0258 (18)*0.430 (5)
C130.6710 (3)0.156 (2)0.5457 (10)0.018 (3)*0.430 (5)
H130.67240.12730.47050.0258 (18)*0.430 (5)
C140.4528 (2)0.8849 (18)0.3096 (6)0.002 (2)*0.430 (5)
C150.4242 (2)0.8172 (17)0.3677 (7)0.004 (2)*0.430 (5)
H150.42250.90080.43600.0258 (18)*0.430 (5)
C160.3984 (2)0.6258 (16)0.3234 (6)0.0046 (19)*0.430 (5)
H160.37860.57790.36070.0258 (18)*0.430 (5)
C170.4019 (3)0.5035 (19)0.2230 (7)0.007 (2)*0.430 (5)
C180.4285 (2)0.5890 (16)0.1599 (6)0.010 (2)*0.430 (5)
H180.42830.52490.08730.0258 (18)*0.430 (5)
C190.4554 (3)0.772 (2)0.2081 (7)0.012 (2)*0.430 (5)
H190.47540.81950.17130.0258 (18)*0.430 (5)
C200.3689 (3)0.211 (2)0.0922 (8)0.010 (2)*0.430 (5)
H200.38290.28870.04130.0258 (18)*0.430 (5)
C210.3428 (3)0.0037 (19)0.0514 (8)0.010 (2)*0.430 (5)
C220.3182 (2)0.095 (2)0.1187 (8)0.011 (2)*0.430 (5)
H220.31830.02060.18970.0258 (18)*0.430 (5)
C230.2932 (2)0.3004 (18)0.0786 (7)0.013 (2)*0.430 (5)
H230.27610.36840.12240.0258 (18)*0.430 (5)
C240.2936 (4)0.404 (3)0.0268 (9)0.008 (3)*0.430 (5)
C250.3166 (2)0.3103 (15)0.0955 (6)0.0057 (16)*0.430 (5)
H250.31640.38300.16680.0258 (18)*0.430 (5)
C260.3404 (3)0.1018 (19)0.0546 (8)0.012 (2)*0.430 (5)
H260.35560.02260.10150.0258 (18)*0.430 (5)
S1A0.49615 (6)1.1094 (5)0.32496 (19)0.0218 (6)*0.570 (5)
O1A0.51043 (19)1.2534 (14)0.2448 (6)0.0282 (16)*0.570 (5)
O2A0.48065 (15)1.2442 (11)0.4150 (5)0.0198 (14)*0.570 (5)
O3A0.74189 (17)0.7026 (12)0.7220 (4)0.0172 (13)*0.570 (5)
O4A0.70790 (14)0.7076 (13)0.8510 (5)0.0184 (13)*0.570 (5)
O5A0.2709 (2)0.7370 (12)0.1443 (5)0.0226 (17)*0.570 (5)
O6A0.23801 (17)0.6636 (15)0.0178 (6)0.0193 (16)*0.570 (5)
N1A0.6112 (2)0.3016 (18)0.5041 (6)0.0242 (18)*0.570 (5)
N2A0.7165 (4)0.600 (2)0.7566 (12)0.030 (4)*0.570 (5)
N3A0.3844 (3)0.3253 (19)0.1035 (7)0.030 (2)*0.570 (5)
N4A0.26429 (17)0.6131 (15)0.0606 (6)0.0032 (16)*0.570 (5)
C1A0.5306 (2)0.8849 (17)0.3881 (6)0.019 (2)*0.570 (5)
C2A0.5286 (2)0.7610 (17)0.4883 (6)0.019 (2)*0.570 (5)
H2A0.51000.81150.52980.0258 (18)*0.570 (5)
C3A0.55425 (19)0.5632 (14)0.5266 (5)0.0198 (18)*0.570 (5)
H3A0.55170.46570.59140.0258 (18)*0.570 (5)
C4A0.5837 (2)0.5055 (18)0.4714 (6)0.019 (2)*0.570 (5)
C5A0.5841 (2)0.6295 (17)0.3696 (7)0.028 (2)*0.570 (5)
H5A0.60290.58020.32810.0258 (18)*0.570 (5)
C6A0.5584 (2)0.8201 (18)0.3278 (8)0.026 (2)*0.570 (5)
H6A0.55960.90540.25950.0258 (18)*0.570 (5)
C7A0.6139 (3)0.204 (2)0.5993 (8)0.029 (2)*0.570 (5)
H7A0.59780.26630.64740.0258 (18)*0.570 (5)
C8A0.6421 (2)0.0075 (17)0.6372 (7)0.016 (2)*0.570 (5)
C9A0.6425 (2)0.1132 (17)0.7415 (7)0.021 (2)*0.570 (5)
H9A0.62530.05790.78720.0258 (18)*0.570 (5)
C10A0.6697 (3)0.305 (2)0.7750 (10)0.024 (3)*0.570 (5)
H10A0.67230.36920.84820.0258 (18)*0.570 (5)
C11A0.6935 (4)0.407 (3)0.7073 (9)0.015 (4)*0.570 (5)
C12A0.6924 (3)0.313 (2)0.6022 (9)0.016 (3)*0.570 (5)
H12A0.70850.37740.55480.0258 (18)*0.570 (5)
C13A0.6657 (2)0.1146 (18)0.5705 (7)0.022 (2)*0.570 (5)
H13A0.66350.04780.49770.0258 (18)*0.570 (5)
C14A0.4607 (2)0.8832 (17)0.2627 (6)0.0121 (18)*0.570 (5)
C15A0.4331 (2)0.7988 (18)0.3184 (7)0.024 (2)*0.570 (5)
H15A0.43140.86910.38900.0258 (18)*0.570 (5)
C16A0.4075 (2)0.6074 (15)0.2693 (6)0.025 (2)*0.570 (5)
H16A0.38890.53760.30740.0258 (18)*0.570 (5)
C17A0.4099 (2)0.5224 (18)0.1636 (6)0.022 (2)*0.570 (5)
C18A0.43872 (18)0.6010 (13)0.1085 (6)0.0181 (18)*0.570 (5)
H18A0.44070.52860.03840.0258 (18)*0.570 (5)
C19A0.4641 (2)0.7859 (17)0.1582 (6)0.024 (2)*0.570 (5)
H19A0.48370.84660.12210.0258 (18)*0.570 (5)
C20A0.3647 (2)0.190 (2)0.1491 (8)0.023 (2)*0.570 (5)
H20A0.36510.21640.22540.0258 (18)*0.570 (5)
C21A0.3390 (2)0.0212 (18)0.0904 (7)0.018 (2)*0.570 (5)
C22A0.3131 (2)0.1458 (16)0.1459 (7)0.0133 (19)*0.570 (5)
H22A0.31200.09210.21910.0258 (18)*0.570 (5)
C23A0.28862 (16)0.3449 (14)0.0989 (5)0.0086 (13)*0.570 (5)
H23A0.27170.43350.13810.0258 (18)*0.570 (5)
C24A0.2909 (3)0.404 (2)0.0090 (6)0.008 (2)*0.570 (5)
C25A0.3154 (2)0.2804 (15)0.0688 (6)0.0173 (18)*0.570 (5)
H25A0.31530.32750.14340.0258 (18)*0.570 (5)
C26A0.3401 (3)0.0881 (19)0.0189 (7)0.022 (2)*0.570 (5)
H26A0.35740.00380.05820.0258 (18)*0.570 (5)
Geometric parameters (Å, º) top
S1—O11.435 (7)S1A—O1A1.384 (7)
S1—O21.497 (7)S1A—O2A1.482 (7)
S1—C141.768 (9)S1A—C1A1.768 (9)
S1—C11.770 (10)S1A—C14A1.792 (8)
O3—N21.305 (17)O3A—N2A1.194 (17)
O4—N21.148 (17)O4A—N2A1.362 (17)
O5—N41.103 (11)O5A—N4A1.256 (10)
O6—N41.343 (13)O6A—N4A1.195 (8)
N1—C71.329 (12)N1A—C7A1.261 (12)
N1—C41.395 (13)N1A—C4A1.435 (12)
N2—C111.53 (2)N2A—C11A1.351 (15)
N3—C201.270 (13)N3A—C20A1.185 (11)
N3—C171.416 (13)N3A—C17A1.467 (13)
N4—C241.482 (17)N4A—C24A1.494 (12)
C1—C21.378 (7)C1A—C6A1.390 (7)
C1—C61.389 (7)C1A—C2A1.392 (7)
C2—C31.383 (7)C2A—C3A1.384 (7)
C2—H20.9500C2A—H2A0.9500
C3—C41.394 (7)C3A—C4A1.393 (6)
C3—H30.9500C3A—H3A0.9500
C4—C51.409 (7)C4A—C5A1.401 (7)
C5—C61.407 (7)C5A—C6A1.373 (7)
C5—H50.9500C5A—H5A0.9500
C6—H60.9500C6A—H6A0.9500
C7—C81.447 (14)C7A—C8A1.491 (14)
C7—H70.9500C7A—H7A0.9500
C8—C131.382 (8)C8A—C13A1.387 (7)
C8—C91.389 (8)C8A—C9A1.389 (7)
C9—C101.388 (9)C9A—C10A1.388 (8)
C9—H90.9500C9A—H9A0.9500
C10—C111.364 (9)C10A—C11A1.393 (8)
C10—H100.9500C10A—H10A0.9500
C11—C121.389 (9)C11A—C12A1.375 (8)
C12—C131.380 (9)C12A—C13A1.394 (8)
C12—H120.9500C12A—H12A0.9500
C13—H130.9500C13A—H13A0.9500
C14—C191.388 (7)C14A—C15A1.374 (6)
C14—C151.400 (7)C14A—C19A1.402 (7)
C15—C161.385 (7)C15A—C16A1.401 (7)
C15—H150.9500C15A—H15A0.9500
C16—C171.403 (7)C16A—C17A1.388 (7)
C16—H160.9500C16A—H16A0.9500
C17—C181.404 (7)C17A—C18A1.398 (7)
C18—C191.399 (7)C18A—C19A1.377 (7)
C18—H180.9500C18A—H18A0.9500
C19—H190.9500C19A—H19A0.9500
C20—C211.464 (15)C20A—C21A1.512 (13)
C20—H200.9500C20A—H20A0.9500
C21—C261.386 (8)C21A—C22A1.397 (7)
C21—C221.393 (8)C21A—C26A1.398 (7)
C22—C231.401 (8)C22A—C23A1.392 (7)
C22—H220.9500C22A—H22A0.9500
C23—C241.402 (8)C23A—C24A1.381 (7)
C23—H230.9500C23A—H23A0.9500
C24—C251.367 (8)C24A—C25A1.387 (7)
C25—C261.388 (8)C25A—C26A1.386 (7)
C25—H250.9500C25A—H25A0.9500
C26—H260.9500C26A—H26A0.9500
O1—S1—O2118.4 (4)O1A—S1A—O2A122.7 (4)
O1—S1—C14110.9 (4)O1A—S1A—C1A108.1 (4)
O2—S1—C14105.8 (4)O2A—S1A—C1A106.2 (4)
O1—S1—C1110.6 (4)O1A—S1A—C14A109.8 (4)
O2—S1—C1105.7 (4)O2A—S1A—C14A105.2 (3)
C14—S1—C1104.4 (5)C1A—S1A—C14A103.1 (4)
C7—N1—C4120.8 (8)C7A—N1A—C4A118.7 (8)
O4—N2—O3128.8 (11)O3A—N2A—C11A127.0 (14)
O4—N2—C11118.2 (12)O3A—N2A—O4A116.1 (9)
O3—N2—C11112.5 (11)C11A—N2A—O4A116.5 (13)
C20—N3—C17122.4 (8)C20A—N3A—C17A121.1 (9)
O5—N4—O6127.9 (13)O6A—N4A—O5A122.4 (9)
O5—N4—C24120.3 (11)O6A—N4A—C24A118.3 (8)
O6—N4—C24111.6 (8)O5A—N4A—C24A119.2 (6)
C2—C1—C6121.1 (9)C6A—C1A—C2A121.4 (8)
C2—C1—S1120.0 (7)C6A—C1A—S1A116.1 (6)
C6—C1—S1119.0 (6)C2A—C1A—S1A122.3 (6)
C1—C2—C3119.3 (8)C3A—C2A—C1A119.1 (7)
C1—C2—H2120.4C3A—C2A—H2A120.5
C3—C2—H2120.4C1A—C2A—H2A120.5
C2—C3—C4121.9 (8)C2A—C3A—C4A120.8 (7)
C2—C3—H3119.1C2A—C3A—H3A119.6
C4—C3—H3119.1C4A—C3A—H3A119.6
C3—C4—N1115.6 (7)C3A—C4A—C5A118.0 (8)
C3—C4—C5117.3 (8)C3A—C4A—N1A124.6 (7)
N1—C4—C5126.8 (7)C5A—C4A—N1A116.9 (6)
C6—C5—C4120.5 (8)C6A—C5A—C4A122.2 (8)
C6—C5—H5119.7C6A—C5A—H5A118.9
C4—C5—H5119.7C4A—C5A—H5A118.9
C1—C6—C5119.0 (8)C5A—C6A—C1A118.2 (8)
C1—C6—H6120.5C5A—C6A—H6A120.9
C5—C6—H6120.5C1A—C6A—H6A120.9
N1—C7—C8122.5 (10)N1A—C7A—C8A120.7 (10)
N1—C7—H7118.7N1A—C7A—H7A119.7
C8—C7—H7118.7C8A—C7A—H7A119.7
C13—C8—C9120.3 (9)C13A—C8A—C9A119.4 (8)
C13—C8—C7119.4 (9)C13A—C8A—C7A123.0 (8)
C9—C8—C7120.2 (9)C9A—C8A—C7A117.5 (7)
C10—C9—C8125.9 (12)C10A—C9A—C8A115.8 (9)
C10—C9—H9117.0C10A—C9A—H9A122.1
C8—C9—H9117.0C8A—C9A—H9A122.1
C11—C10—C9113.5 (15)C9A—C10A—C11A123.7 (12)
C11—C10—H10123.3C9A—C10A—H10A118.1
C9—C10—H10123.3C11A—C10A—H10A118.1
C10—C11—C12120.5 (18)N2A—C11A—C12A126.2 (12)
C10—C11—N2128.3 (13)N2A—C11A—C10A112.9 (11)
C12—C11—N2111.0 (12)C12A—C11A—C10A120.9 (13)
C13—C12—C11126.4 (19)C11A—C12A—C13A114.8 (12)
C13—C12—H12116.8C11A—C12A—H12A122.6
C11—C12—H12116.8C13A—C12A—H12A122.6
C12—C13—C8113.1 (14)C8A—C13A—C12A125.0 (9)
C12—C13—H13123.5C8A—C13A—H13A117.5
C8—C13—H13123.5C12A—C13A—H13A117.5
C19—C14—C15122.0 (8)C15A—C14A—C19A122.4 (8)
C19—C14—S1117.8 (6)C15A—C14A—S1A121.0 (6)
C15—C14—S1120.2 (6)C19A—C14A—S1A116.5 (5)
C16—C15—C14118.6 (8)C14A—C15A—C16A119.0 (8)
C16—C15—H15120.7C14A—C15A—H15A120.5
C14—C15—H15120.7C16A—C15A—H15A120.5
C15—C16—C17119.4 (8)C17A—C16A—C15A118.3 (7)
C15—C16—H16120.3C17A—C16A—H16A120.9
C17—C16—H16120.3C15A—C16A—H16A120.9
C16—C17—C18122.0 (8)C16A—C17A—C18A122.6 (8)
C16—C17—N3113.7 (7)C16A—C17A—N3A123.2 (7)
C18—C17—N3124.2 (7)C18A—C17A—N3A114.0 (6)
C19—C18—C17117.4 (8)C19A—C18A—C17A118.4 (7)
C19—C18—H18121.3C19A—C18A—H18A120.8
C17—C18—H18121.3C17A—C18A—H18A120.8
C14—C19—C18120.0 (8)C18A—C19A—C14A119.1 (7)
C14—C19—H19120.0C18A—C19A—H19A120.4
C18—C19—H19120.0C14A—C19A—H19A120.4
N3—C20—C21126.2 (10)N3A—C20A—C21A122.5 (10)
N3—C20—H20116.9N3A—C20A—H20A118.7
C21—C20—H20116.9C21A—C20A—H20A118.7
C26—C21—C22119.9 (9)C22A—C21A—C26A119.6 (8)
C26—C21—C20121.4 (8)C22A—C21A—C20A119.2 (7)
C22—C21—C20118.5 (8)C26A—C21A—C20A121.1 (7)
C21—C22—C23118.0 (8)C23A—C22A—C21A123.2 (7)
C21—C22—H22121.0C23A—C22A—H22A118.4
C23—C22—H22121.0C21A—C22A—H22A118.4
C22—C23—C24119.4 (8)C24A—C23A—C22A114.7 (6)
C22—C23—H23120.3C24A—C23A—H23A122.6
C24—C23—H23120.3C22A—C23A—H23A122.6
C25—C24—C23123.4 (9)C23A—C24A—C25A124.4 (7)
C25—C24—N4111.9 (8)C23A—C24A—N4A115.0 (6)
C23—C24—N4124.6 (8)C25A—C24A—N4A120.6 (7)
C24—C25—C26115.8 (8)C26A—C25A—C24A119.5 (7)
C24—C25—H25122.1C26A—C25A—H25A120.2
C26—C25—H25122.1C24A—C25A—H25A120.2
C21—C26—C25123.2 (9)C25A—C26A—C21A118.5 (8)
C21—C26—H26118.4C25A—C26A—H26A120.8
C25—C26—H26118.4C21A—C26A—H26A120.8
O1—S1—C1—C2157.0 (8)O1A—S1A—C1A—C6A21.5 (9)
O2—S1—C1—C227.6 (10)O2A—S1A—C1A—C6A154.9 (7)
C14—S1—C1—C283.7 (9)C14A—S1A—C1A—C6A94.7 (8)
O1—S1—C1—C624.3 (10)O1A—S1A—C1A—C2A163.8 (8)
O2—S1—C1—C6153.6 (8)O2A—S1A—C1A—C2A30.4 (9)
C14—S1—C1—C695.1 (9)C14A—S1A—C1A—C2A79.9 (8)
C6—C1—C2—C30.7 (16)C6A—C1A—C2A—C3A2.0 (14)
S1—C1—C2—C3179.4 (8)S1A—C1A—C2A—C3A172.4 (7)
C1—C2—C3—C47.4 (15)C1A—C2A—C3A—C4A5.9 (13)
C2—C3—C4—N1175.0 (9)C2A—C3A—C4A—C5A7.4 (13)
C2—C3—C4—C511.8 (14)C2A—C3A—C4A—N1A179.0 (8)
C7—N1—C4—C3166.7 (9)C7A—N1A—C4A—C3A15.0 (14)
C7—N1—C4—C520.9 (16)C7A—N1A—C4A—C5A173.3 (9)
C3—C4—C5—C69.9 (14)C3A—C4A—C5A—C6A5.3 (14)
N1—C4—C5—C6177.8 (10)N1A—C4A—C5A—C6A177.6 (8)
C2—C1—C6—C51.0 (16)C4A—C5A—C6A—C1A1.7 (15)
S1—C1—C6—C5177.7 (8)C2A—C1A—C6A—C5A0.0 (14)
C4—C5—C6—C13.7 (15)S1A—C1A—C6A—C5A174.8 (7)
C4—N1—C7—C8179.0 (9)C4A—N1A—C7A—C8A179.8 (8)
N1—C7—C8—C13174.1 (10)N1A—C7A—C8A—C13A2.2 (14)
N1—C7—C8—C910.0 (15)N1A—C7A—C8A—C9A177.5 (9)
C13—C8—C9—C101.2 (19)C13A—C8A—C9A—C10A6.1 (13)
C7—C8—C9—C10174.8 (11)C7A—C8A—C9A—C10A178.4 (9)
C8—C9—C10—C115 (2)C8A—C9A—C10A—C11A5.6 (16)
C9—C10—C11—C125 (3)O3A—N2A—C11A—C12A7 (2)
C9—C10—C11—N2179.8 (17)O4A—N2A—C11A—C12A165.8 (13)
O4—N2—C11—C104 (3)O3A—N2A—C11A—C10A172.2 (12)
O3—N2—C11—C10167.6 (17)O4A—N2A—C11A—C10A14.7 (17)
O4—N2—C11—C12170.8 (14)C9A—C10A—C11A—N2A177.3 (12)
O3—N2—C11—C1217 (2)C9A—C10A—C11A—C12A3 (2)
C10—C11—C12—C131 (3)N2A—C11A—C12A—C13A179.5 (13)
N2—C11—C12—C13176.7 (15)C10A—C11A—C12A—C13A1.0 (19)
C11—C12—C13—C83 (2)C9A—C8A—C13A—C12A4.6 (15)
C9—C8—C13—C123.0 (17)C7A—C8A—C13A—C12A179.9 (10)
C7—C8—C13—C12178.9 (11)C11A—C12A—C13A—C8A1.9 (16)
O1—S1—C14—C1934.5 (9)O1A—S1A—C14A—C15A154.5 (8)
O2—S1—C14—C19164.0 (8)O2A—S1A—C14A—C15A20.6 (8)
C1—S1—C14—C1984.7 (9)C1A—S1A—C14A—C15A90.5 (8)
O1—S1—C14—C15148.5 (7)O1A—S1A—C14A—C19A29.3 (8)
O2—S1—C14—C1518.9 (9)O2A—S1A—C14A—C19A163.2 (7)
C1—S1—C14—C1592.3 (8)C1A—S1A—C14A—C19A85.7 (7)
C19—C14—C15—C162.0 (15)C19A—C14A—C15A—C16A0.3 (14)
S1—C14—C15—C16174.9 (7)S1A—C14A—C15A—C16A175.6 (7)
C14—C15—C16—C170.8 (14)C14A—C15A—C16A—C17A3.5 (13)
C15—C16—C17—C186.8 (15)C15A—C16A—C17A—C18A5.9 (13)
C15—C16—C17—N3177.6 (8)C15A—C16A—C17A—N3A179.4 (9)
C20—N3—C17—C16165.7 (9)C20A—N3A—C17A—C16A14.2 (14)
C20—N3—C17—C189.7 (15)C20A—N3A—C17A—C18A160.9 (9)
C16—C17—C18—C199.8 (15)C16A—C17A—C18A—C19A4.9 (13)
N3—C17—C18—C19175.1 (9)N3A—C17A—C18A—C19A179.9 (8)
C15—C14—C19—C181.2 (15)C17A—C18A—C19A—C14A1.5 (12)
S1—C14—C19—C18178.2 (7)C15A—C14A—C19A—C18A0.7 (14)
C17—C18—C19—C146.9 (15)S1A—C14A—C19A—C18A176.8 (6)
C17—N3—C20—C21176.7 (9)C17A—N3A—C20A—C21A177.9 (8)
N3—C20—C21—C26175.9 (10)N3A—C20A—C21A—C22A171.3 (9)
N3—C20—C21—C229.0 (16)N3A—C20A—C21A—C26A6.8 (14)
C26—C21—C22—C234.5 (15)C26A—C21A—C22A—C23A2.7 (14)
C20—C21—C22—C23179.8 (9)C20A—C21A—C22A—C23A179.2 (8)
C21—C22—C23—C240.4 (15)C21A—C22A—C23A—C24A2.4 (12)
C22—C23—C24—C252.1 (19)C22A—C23A—C24A—C25A0.4 (14)
C22—C23—C24—N4179.3 (10)C22A—C23A—C24A—N4A178.8 (7)
O5—N4—C24—C250.6 (17)O6A—N4A—C24A—C23A18.0 (12)
O6—N4—C24—C25176.2 (9)O5A—N4A—C24A—C23A159.2 (7)
O5—N4—C24—C23178.2 (11)O6A—N4A—C24A—C25A161.3 (8)
O6—N4—C24—C232.6 (17)O5A—N4A—C24A—C25A21.5 (13)
C23—C24—C25—C260.3 (18)C23A—C24A—C25A—C26A1.3 (15)
N4—C24—C25—C26179.1 (9)N4A—C24A—C25A—C26A179.5 (8)
C22—C21—C26—C256.7 (15)C24A—C25A—C26A—C21A1.0 (14)
C20—C21—C26—C25178.2 (9)C22A—C21A—C26A—C25A0.8 (15)
C24—C25—C26—C214.1 (15)C20A—C21A—C26A—C25A178.9 (8)

Experimental details

Crystal data
Chemical formulaC26H18N4O6S
Mr514.5
Crystal system, space groupMonoclinic, Cc
Temperature (K)120
a, b, c (Å)36.706 (3), 4.9130 (4), 12.364 (5)
β (°) 98.808 (4)
V3)2203.4 (9)
Z4
Radiation typeSynchrotron, λ = 0.6934 Å
µ (mm1)0.20
Crystal size (mm)0.15 × 0.05 × 0.02
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2000)
Tmin, Tmax0.970, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
9138, 4141, 3069
Rint0.036
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.01
No. of reflections4141
No. of parameters299
No. of restraints50
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.44
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.3 (2)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SIR97 (Altomare et al., 1999), SHELXL97-2 (Sheldrick, 1998), PLATON (Spek, 2002), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
S1—O11.435 (7)S1A—O1A1.384 (7)
S1—O21.497 (7)S1A—O2A1.482 (7)
S1—C141.768 (9)S1A—C1A1.768 (9)
S1—C11.770 (10)S1A—C14A1.792 (8)
O3—N21.305 (17)O3A—N2A1.194 (17)
O4—N21.148 (17)O4A—N2A1.362 (17)
O5—N41.103 (11)O5A—N4A1.256 (10)
O6—N41.343 (13)O6A—N4A1.195 (8)
O1—S1—O2118.4 (4)O1A—S1A—O2A122.7 (4)
Intermolecular contacts between nitro group atoms top
Atom 1Atom 2Distance(Å)Symmetry applied to Atom 2
O3O52.937 (10)0.5 + x,0.5 + y,1 + z
O3O62.718 (12)0.5 + x,-1.5 − y,0.5 + z
O4N42.816 (13)0.5 + x,-0.5 + y,1 + z
O3AO5A2.926 (8)0.5 + x,0.5 + y,1 + z
O4AO6A2.885 (9)0.5 + x,-0.5 + y,1 + z
O4AN4A2.959 (9)0.5 + x,-0.5 + y,1 + z
O5AN2A2.815 (15)-0.5 + x,-0.5 + y,-1 + z
 

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