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The title compound (BM531), C17H26N4O5S, has been designed for use as both a thromboxane synthase inhibitor (TXSI) and a thromboxane receptor antagonist (TXRA). We report here the X-ray crystal structure determination of the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102016463/gg1135sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102016463/gg1135Isup2.hkl
Contains datablock I

CCDC reference: 197343

Comment top

N-tert-Butyl-N'-[(2-cyclohexylamino-5-nitrobenzene)sulfonyl]urea, BM531, (I), is a thromboxane synthase inhibitor (TXSI) and a thromboxane receptor antagonist (TXRA) (Dogné et al., 2001). It crystallizes in space group P21/n with two molecules, A and B, in the asymmetric unit (Fig. 1). For each molecule, a stretched conformation is observed and the two NH (N3 and N4) of the sulfonylurea group are opposite to the carbonyl moiety, and the nitro group is not in the same plane as the phenyl group. Subtle differences between the two molecules can be highlighted from analysis of the O—N2A/B—C10A/B—C and S1—N3—C13—N4 angles, which are different by 10 and 7°, respectively, in molecules A and B (Table 1). \sch

Previously, five conformations, depending on the torsion angles along the sulfonylurea group (Fig. 2), have been reported, namely α, β, γ and δ for pyrid-3-ylsulfonylurea and sulfonylcyanoguanidine (Masereel et al., 1995), and ε for nitro-3-ylsulfonylurea (Michaux et al., 2001) (Table 3). According to these conventions, both molecules of (I) in the asymmetric unit adopt the ε conformation (Table 4). Moreover, this particular conformation was also found in another dual action nitro-3-ylsulfonylurea molecule, BM567 (Michaux et al., 2001). As in BM567, one intramolecular hydrogen bond in (I) (N1A—H12A···O4A/N1B—H12B···O4B) involves one O atom of the sulfonyl group and imposes this conformation on (I) (Table 2). Intermolecular hydrogen bonds were also observed in the crystal packing (Table 2 and Fig. 3). These involve the sulfonylurea moiety, which could be a potential anchoring point for binding with one of the two enzymes.

In addition, the crystal packing of (I) also involves C—H···O interactions that may be classified as weak donor-strong acceptor hydrogen bonds (Desiraju & Steiner, 1999). Indeed, H···A lengths are between 2 and 3 Å, D···A lengths between 3 and 4 Å and X—H···A angles between 90 and 180° (Table 2). The phenyl, the tert-butyl and the sulfone groups of (I) are involved in these. Three of these interactions are intramolecular hydrogen bonds (Table 2) which should contribute in part to the molecular conformation of the sulfonylurea group of (I).

In preliminary conclusion, from the two examples analysed to date, the ε conformation in nitro-3-ylsulfonylurea molecules seems convenient for both thromboxane synthase inhibition and thromboxane receptor antagonism. The active site of these targets would favour such a conformation. In addition, the sulfonylurea group of these compounds would form favourable interactions with the two targets.

Table 1. Selected torsion angles (Å,°) for (I). Table 2. Hydrogen bonding and contact geometry in (I) (Å,°). Table 3. Theoretical torsion angles along the sulfonylurea group for the α, β, γ, δ and ε conformations. Table 4. Torsion angles for the ε conformation of the two asymmetric molecules of (I).

Experimental top

Crystals of (I) were obtained by slow evaporation of an ethanol-toluene (Ratio?) solution of BM531, to give colourless crystals suitable for X-ray analysis.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the two molecules in the asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The definition of the theoretical torsion angles along the sulfonylurea group in this class of compounds. Thus, ϕ1 is the angle 1–2-3–4, ϕ2 2–3-4–5, ϕ3 3–4-5–6 and ϕ4 4–5-6–7; see also Table 3.
[Figure 3] Fig. 3. A packing diagram for (I).
N-tert-Butyl-N'-[(2-cyclohexylamino-5-nitrobenzene)sulfonyl]urea top
Crystal data top
C17H26N4O5SF(000) = 1696
Mr = 398.49Dx = 1.272 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P2ynCell parameters from 25 reflections
a = 14.447 (5) Åθ = 30–40°
b = 11.579 (5) ŵ = 1.68 mm1
c = 24.981 (5) ÅT = 293 K
β = 95.195 (5)°Polyhedral, colourless
V = 4162 (2) Å30.42 × 0.17 × 0.13 mm
Z = 8
Data collection top
Enraf-Nonius CAD-4
diffractometer
5832 reflections with I > 2σ(I)
Radiation source: long fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 71.9°, θmin = 3.4°
θ/2θ scansh = 1712
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
k = 014
Tmin = 0.539, Tmax = 0.811l = 3030
11170 measured reflections3 standard reflections every 200 reflections
8166 independent reflections intensity decay: 5%
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0713P)2 + 0.7284P]
where P = (Fo2 + 2Fc2)/3
8166 reflections(Δ/σ)max = 0.003
487 parametersΔρmax = 0.21 e Å3
6 restraintsΔρmin = 0.51 e Å3
Crystal data top
C17H26N4O5SV = 4162 (2) Å3
Mr = 398.49Z = 8
Monoclinic, P21/nCu Kα radiation
a = 14.447 (5) ŵ = 1.68 mm1
b = 11.579 (5) ÅT = 293 K
c = 24.981 (5) Å0.42 × 0.17 × 0.13 mm
β = 95.195 (5)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
5832 reflections with I > 2σ(I)
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
Rint = 0.018
Tmin = 0.539, Tmax = 0.8113 standard reflections every 200 reflections
11170 measured reflections intensity decay: 5%
8166 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0476 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.04Δρmax = 0.21 e Å3
8166 reflectionsΔρmin = 0.51 e Å3
487 parameters
Special details top

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.46669 (4)0.02237 (5)0.24699 (2)0.0466 (2)
O1A0.80450 (16)0.2815 (2)0.20364 (13)0.1230 (13)
O2A0.74021 (18)0.2673 (2)0.27740 (13)0.1237 (11)
O3A0.46468 (11)0.04913 (14)0.29378 (6)0.0599 (6)
O4A0.46019 (11)0.14478 (13)0.25245 (6)0.0589 (6)
O5A0.41749 (10)0.20065 (13)0.20135 (7)0.0611 (5)
N1A0.53714 (13)0.13700 (16)0.14839 (7)0.0564 (7)
N2A0.74950 (16)0.2366 (2)0.23159 (14)0.0877 (12)
N3A0.37813 (11)0.01102 (15)0.20431 (7)0.0491 (6)
N4A0.28812 (13)0.13824 (16)0.15100 (8)0.0585 (7)
C1A0.53941 (15)0.1894 (2)0.09529 (9)0.0537 (8)
C2A0.4778 (2)0.1241 (2)0.05376 (11)0.0714 (10)
C3A0.4715 (3)0.1823 (3)0.00108 (12)0.0958 (15)
C4A0.4403 (3)0.3062 (3)0.00271 (13)0.0974 (16)
C5A0.5032 (2)0.3720 (3)0.04342 (12)0.0878 (11)
C6A0.5098 (2)0.3147 (2)0.09853 (10)0.0684 (9)
C7A0.58536 (14)0.04404 (19)0.16714 (9)0.0479 (7)
C8A0.65903 (16)0.0024 (2)0.14019 (10)0.0638 (9)
C9A0.71074 (17)0.0927 (2)0.16067 (12)0.0696 (10)
C10A0.69264 (16)0.1424 (2)0.20900 (11)0.0616 (8)
C11A0.61940 (14)0.1041 (2)0.23583 (10)0.0542 (7)
C12A0.56534 (14)0.01352 (18)0.21489 (8)0.0454 (6)
C13A0.36302 (14)0.12446 (19)0.18585 (9)0.0482 (7)
C14A0.25455 (13)0.25131 (19)0.13039 (8)0.0613 (8)
C15A0.3278 (2)0.3117 (3)0.10019 (13)0.1011 (16)
C16A0.2279 (2)0.3258 (2)0.17688 (10)0.0748 (10)
C17A0.1687 (2)0.2257 (3)0.09223 (16)0.1209 (17)
S1B0.21534 (3)0.27040 (5)0.13474 (2)0.0478 (2)
O1B0.15411 (18)0.0460 (2)0.06604 (9)0.1022 (10)
O2B0.27329 (18)0.0384 (2)0.00824 (9)0.0985 (9)
O3B0.29995 (10)0.20668 (15)0.14425 (7)0.0635 (6)
O4B0.21782 (11)0.39360 (13)0.13476 (7)0.0612 (6)
O5B0.15095 (13)0.04467 (13)0.16326 (7)0.0679 (6)
N1B0.03366 (13)0.36284 (18)0.07664 (8)0.0618 (7)
N2B0.19627 (19)0.0056 (2)0.02550 (9)0.0726 (9)
N3B0.14646 (12)0.23777 (15)0.18043 (7)0.0495 (6)
N4B0.05295 (13)0.11285 (16)0.22201 (8)0.0565 (6)
C1B0.06215 (17)0.4043 (2)0.06522 (10)0.0672 (9)
C2B0.12715 (19)0.3358 (3)0.09666 (14)0.0865 (13)
C3B0.2267 (2)0.3803 (4)0.0865 (2)0.124 (2)
C4B0.2325 (2)0.5068 (4)0.09838 (17)0.1114 (16)
C5B0.1664 (3)0.5758 (4)0.06833 (18)0.1183 (17)
C6B0.0669 (2)0.5317 (3)0.07904 (14)0.0868 (11)
C7B0.07040 (15)0.2698 (2)0.05421 (9)0.0514 (7)
C8B0.02456 (18)0.2138 (2)0.00885 (10)0.0661 (9)
C9B0.06481 (18)0.1259 (2)0.01700 (10)0.0661 (9)
C10B0.15207 (17)0.0867 (2)0.00223 (9)0.0556 (8)
C11B0.19740 (15)0.13206 (19)0.04822 (8)0.0506 (7)
C12B0.15755 (14)0.22224 (19)0.07399 (8)0.0460 (7)
C13B0.11742 (16)0.12309 (19)0.18804 (8)0.0508 (7)
C14B0.01291 (19)0.0021 (2)0.23828 (11)0.0676 (9)
C15B0.0299 (3)0.0616 (3)0.18795 (14)0.1151 (17)
C16B0.0878 (2)0.0705 (2)0.26841 (12)0.0825 (11)
C17B0.0621 (2)0.0333 (3)0.27495 (16)0.1103 (16)
H1A0.603400.186900.085200.0640*
H2A0.502000.046500.050500.0860*
H3A0.416000.117900.065700.0860*
H4A0.427800.140500.025700.1150*
H5A0.531800.179900.015200.1150*
H6A0.377200.308300.013000.1170*
H7A0.440700.342800.032200.1170*
H8A0.479700.450000.046400.1060*
H9A0.564800.377000.031100.1060*
H10A0.449800.318700.113000.0820*
H11A0.554400.356200.122800.0820*
H12A0.501300.168900.169800.0680*
H13A0.672300.029700.107600.0770*
H14A0.758700.121400.142100.0840*
H15A0.606400.138900.267900.0650*
H16A0.339900.042300.192900.0590*
H17A0.257700.077600.140000.0700*
H18A0.342600.264500.070600.1520*
H19A0.382800.324000.124100.1520*
H20A0.304100.384800.086900.1520*
H21A0.282500.342700.200400.1120*
H22A0.200600.396500.163100.1120*
H23A0.184000.284900.196400.1120*
H24A0.143800.296600.077100.1820*
H25A0.122700.188200.111600.1820*
H26A0.185400.176000.063900.1820*
H1B0.080700.394500.026800.0810*
H2B0.125000.255200.086400.1040*
H3B0.107200.341300.134700.1040*
H4B0.266400.338100.109000.1480*
H5B0.249100.366500.049300.1480*
H6B0.218400.519100.136700.1340*
H7B0.295400.533400.088600.1340*
H8B0.169000.656100.079100.1420*
H9B0.185300.571500.030100.1420*
H10B0.045500.543100.116600.1040*
H11B0.026400.575100.057500.1040*
H12B0.069300.401300.099600.0740*
H13B0.034900.237700.003700.0790*
H14B0.033800.092500.047400.0790*
H15B0.254500.102200.061900.0610*
H16B0.127300.291600.200400.0590*
H17B0.032800.175200.235700.0680*
H18B0.076000.013400.169000.1720*
H19B0.017900.079400.165000.1720*
H20B0.058500.131900.198500.1720*
H21B0.136800.084700.245700.1240*
H22B0.061700.142700.278500.1240*
H23B0.112400.030100.300100.1240*
H24B0.094000.035500.284300.1660*
H25B0.033900.069200.307000.1660*
H26B0.105600.085800.256600.1660*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0467 (3)0.0482 (3)0.0458 (3)0.0011 (2)0.0084 (2)0.0044 (2)
O1A0.0804 (15)0.0921 (17)0.200 (3)0.0382 (13)0.0326 (17)0.0196 (17)
O2A0.1056 (19)0.121 (2)0.143 (2)0.0440 (16)0.0029 (17)0.0544 (18)
O3A0.0632 (10)0.0701 (11)0.0471 (8)0.0009 (8)0.0087 (7)0.0146 (7)
O4A0.0674 (10)0.0473 (9)0.0636 (10)0.0001 (7)0.0149 (8)0.0063 (7)
O5A0.0483 (8)0.0460 (9)0.0863 (11)0.0029 (7)0.0090 (8)0.0100 (8)
N1A0.0611 (11)0.0564 (12)0.0546 (11)0.0079 (9)0.0210 (9)0.0119 (9)
N2A0.0525 (13)0.0707 (16)0.139 (3)0.0136 (12)0.0032 (15)0.0199 (17)
N3A0.0409 (9)0.0432 (10)0.0619 (11)0.0022 (7)0.0021 (8)0.0090 (8)
N4A0.0531 (11)0.0513 (11)0.0679 (12)0.0004 (9)0.0123 (9)0.0093 (9)
C1A0.0505 (12)0.0576 (14)0.0545 (13)0.0028 (10)0.0125 (10)0.0109 (11)
C2A0.0814 (18)0.0635 (16)0.0691 (16)0.0048 (14)0.0054 (14)0.0018 (13)
C3A0.119 (3)0.103 (3)0.0620 (17)0.002 (2)0.0099 (17)0.0037 (17)
C4A0.105 (3)0.105 (3)0.079 (2)0.008 (2)0.0091 (18)0.0308 (19)
C5A0.111 (2)0.0672 (18)0.086 (2)0.0013 (17)0.0128 (18)0.0300 (16)
C6A0.0841 (18)0.0545 (15)0.0676 (16)0.0077 (13)0.0121 (13)0.0101 (12)
C7A0.0420 (11)0.0495 (12)0.0527 (12)0.0048 (9)0.0078 (9)0.0028 (10)
C8A0.0529 (13)0.0748 (17)0.0664 (15)0.0051 (12)0.0199 (11)0.0066 (13)
C9A0.0473 (13)0.0736 (17)0.0896 (19)0.0091 (12)0.0155 (12)0.0030 (15)
C10A0.0417 (11)0.0539 (14)0.0883 (18)0.0046 (10)0.0007 (11)0.0052 (13)
C11A0.0443 (11)0.0532 (13)0.0640 (14)0.0039 (10)0.0013 (10)0.0056 (11)
C12A0.0399 (10)0.0464 (12)0.0498 (11)0.0029 (9)0.0039 (8)0.0002 (9)
C13A0.0412 (10)0.0485 (12)0.0546 (12)0.0023 (9)0.0030 (9)0.0118 (10)
C14A0.0592 (14)0.0597 (15)0.0631 (14)0.0066 (11)0.0056 (11)0.0037 (12)
C15A0.107 (3)0.112 (3)0.088 (2)0.012 (2)0.0298 (19)0.031 (2)
C16A0.0754 (17)0.0619 (16)0.0881 (19)0.0173 (14)0.0132 (15)0.0051 (14)
C17A0.114 (3)0.097 (3)0.136 (3)0.012 (2)0.074 (2)0.001 (2)
S1B0.0413 (3)0.0508 (3)0.0503 (3)0.0022 (2)0.0007 (2)0.0038 (2)
O1B0.1270 (19)0.1012 (17)0.0804 (14)0.0143 (14)0.0204 (13)0.0428 (13)
O2B0.1058 (17)0.1028 (17)0.0889 (15)0.0338 (14)0.0202 (13)0.0223 (13)
O3B0.0408 (8)0.0794 (12)0.0682 (10)0.0133 (8)0.0065 (7)0.0084 (9)
O4B0.0605 (9)0.0485 (9)0.0742 (11)0.0092 (8)0.0032 (8)0.0035 (8)
O5B0.0956 (13)0.0469 (9)0.0626 (10)0.0141 (9)0.0148 (9)0.0031 (8)
N1B0.0561 (11)0.0637 (13)0.0624 (12)0.0156 (10)0.0122 (9)0.0064 (10)
N2B0.0915 (17)0.0703 (15)0.0595 (13)0.0031 (13)0.0262 (12)0.0121 (11)
N3B0.0602 (11)0.0430 (10)0.0459 (9)0.0065 (8)0.0078 (8)0.0023 (8)
N4B0.0611 (11)0.0476 (11)0.0611 (11)0.0028 (9)0.0076 (9)0.0034 (9)
C1B0.0571 (14)0.0823 (19)0.0598 (14)0.0204 (13)0.0086 (11)0.0039 (13)
C2B0.0623 (17)0.0740 (19)0.121 (3)0.0021 (15)0.0035 (16)0.0076 (18)
C3B0.0594 (19)0.131 (4)0.179 (4)0.000 (2)0.003 (2)0.025 (3)
C4B0.066 (2)0.132 (3)0.137 (3)0.030 (2)0.014 (2)0.007 (3)
C5B0.098 (3)0.118 (3)0.140 (3)0.058 (2)0.016 (2)0.029 (3)
C6B0.0783 (19)0.075 (2)0.108 (2)0.0230 (16)0.0139 (17)0.0236 (17)
C7B0.0516 (12)0.0548 (13)0.0468 (11)0.0027 (10)0.0013 (9)0.0035 (10)
C8B0.0598 (14)0.0790 (18)0.0564 (14)0.0076 (13)0.0122 (11)0.0022 (13)
C9B0.0729 (17)0.0752 (18)0.0485 (13)0.0055 (14)0.0043 (11)0.0077 (12)
C10B0.0693 (15)0.0532 (13)0.0460 (12)0.0036 (11)0.0150 (11)0.0023 (10)
C11B0.0510 (12)0.0553 (13)0.0463 (11)0.0017 (10)0.0083 (9)0.0025 (10)
C12B0.0447 (11)0.0502 (12)0.0431 (11)0.0006 (9)0.0032 (8)0.0022 (9)
C13B0.0591 (13)0.0474 (12)0.0441 (11)0.0081 (10)0.0050 (10)0.0026 (9)
C14B0.0707 (16)0.0596 (15)0.0712 (16)0.0133 (12)0.0007 (13)0.0083 (12)
C15B0.117 (3)0.119 (3)0.103 (3)0.057 (2)0.025 (2)0.001 (2)
C16B0.103 (2)0.0560 (16)0.086 (2)0.0037 (15)0.0051 (17)0.0179 (14)
C17B0.092 (2)0.108 (3)0.137 (3)0.001 (2)0.044 (2)0.036 (2)
Geometric parameters (Å, º) top
S1A—O3A1.4348 (17)C5A—H9A0.9694
S1A—O4A1.4278 (17)C5A—H8A0.9701
S1A—N3A1.6359 (19)C6A—H10A0.9700
S1A—C12A1.748 (2)C6A—H11A0.9710
S1B—C12B1.755 (2)C8A—H13A0.9306
S1B—O3B1.4291 (17)C9A—H14A0.9295
S1B—O4B1.4270 (17)C11A—H15A0.9310
S1B—N3B1.6252 (19)C15A—H19A0.9605
O1A—N2A1.221 (4)C15A—H20A0.9609
O2A—N2A1.217 (5)C15A—H18A0.9589
O5A—C13A1.222 (3)C16A—H22A0.9590
O1B—N2B1.226 (3)C16A—H23A0.9593
O2B—N2B1.217 (4)C16A—H21A0.9601
O5B—C13B1.223 (3)C17A—H24A0.9600
N1A—C1A1.462 (3)C17A—H25A0.9605
N1A—C7A1.343 (3)C17A—H26A0.9598
N2A—C10A1.449 (4)C1B—C6B1.518 (4)
N3A—C13A1.403 (3)C1B—C2B1.504 (4)
N4A—C13A1.336 (3)C2B—C3B1.527 (4)
N4A—C14A1.473 (3)C3B—C4B1.498 (7)
N1A—H12A0.8607C4B—C5B1.498 (6)
N3A—H16A0.8596C5B—C6B1.526 (5)
N4A—H17A0.8601C7B—C8B1.417 (3)
N1B—C1B1.468 (3)C7B—C12B1.421 (3)
N1B—C7B1.345 (3)C8B—C9B1.363 (3)
N2B—C10B1.453 (3)C9B—C10B1.384 (4)
N3B—C13B1.411 (3)C10B—C11B1.374 (3)
N4B—C13B1.321 (3)C11B—C12B1.380 (3)
N4B—C14B1.479 (3)C14B—C15B1.538 (5)
N1B—H12B0.8596C14B—C16B1.515 (4)
N3B—H16B0.8597C14B—C17B1.524 (4)
N4B—H17B0.8608C1B—H1B0.9794
C1A—C2A1.508 (4)C2B—H2B0.9691
C1A—C6A1.517 (3)C2B—H3B0.9698
C2A—C3A1.522 (4)C3B—H4B0.9706
C3A—C4A1.509 (5)C3B—H5B0.9692
C4A—C5A1.508 (5)C4B—H6B0.9710
C5A—C6A1.523 (4)C4B—H7B0.9696
C7A—C12A1.419 (3)C5B—H8B0.9696
C7A—C8A1.416 (3)C5B—H9B0.9705
C8A—C9A1.358 (3)C6B—H10B0.9700
C9A—C10A1.384 (4)C6B—H11B0.9703
C10A—C11A1.376 (3)C8B—H13B0.9295
C11A—C12A1.382 (3)C9B—H14B0.9303
C14A—C15A1.524 (4)C11B—H15B0.9305
C14A—C16A1.524 (3)C15B—H18B0.9602
C14A—C17A1.523 (4)C15B—H19B0.9590
C1A—H1A0.9804C15B—H20B0.9605
C2A—H2A0.9702C16B—H21B0.9606
C2A—H3A0.9693C16B—H22B0.9601
C3A—H4A0.9699C16B—H23B0.9596
C3A—H5A0.9694C17B—H24B0.9597
C4A—H7A0.9701C17B—H25B0.9595
C4A—H6A0.9696C17B—H26B0.9604
O3A—S1A—O4A119.25 (9)C14A—C15A—H18A109.48
O3A—S1A—N3A108.80 (9)H18A—C15A—H19A109.53
O3A—S1A—C12A108.31 (10)H19A—C15A—H20A109.46
O4A—S1A—N3A104.04 (9)H18A—C15A—H20A109.46
O4A—S1A—C12A110.08 (10)C14A—C15A—H20A109.48
N3A—S1A—C12A105.48 (9)C14A—C15A—H19A109.43
O3B—S1B—N3B109.40 (10)C14A—C16A—H21A109.36
O3B—S1B—C12B108.20 (10)H21A—C16A—H22A109.52
O4B—S1B—N3B104.42 (10)H21A—C16A—H23A109.51
O4B—S1B—C12B109.14 (10)C14A—C16A—H23A109.41
N3B—S1B—C12B105.06 (9)C14A—C16A—H22A109.49
O3B—S1B—O4B119.67 (10)H22A—C16A—H23A109.54
C1A—N1A—C7A126.55 (19)C14A—C17A—H25A109.51
O1A—N2A—O2A123.1 (3)H24A—C17A—H26A109.43
O2A—N2A—C10A118.6 (3)H25A—C17A—H26A109.39
O1A—N2A—C10A118.3 (3)C14A—C17A—H24A109.56
S1A—N3A—C13A121.66 (14)C14A—C17A—H26A109.47
C13A—N4A—C14A123.77 (18)H24A—C17A—H25A109.47
C1A—N1A—H12A116.74N1B—C1B—C2B110.4 (2)
C7A—N1A—H12A116.71C2B—C1B—C6B110.5 (2)
S1A—N3A—H16A119.17N1B—C1B—C6B109.6 (2)
C13A—N3A—H16A119.17C1B—C2B—C3B111.0 (3)
C14A—N4A—H17A118.13C2B—C3B—C4B111.4 (3)
C13A—N4A—H17A118.11C3B—C4B—C5B111.9 (3)
C1B—N1B—C7B125.5 (2)C4B—C5B—C6B111.5 (3)
O1B—N2B—C10B117.9 (2)C1B—C6B—C5B110.3 (3)
O2B—N2B—C10B119.2 (2)N1B—C7B—C12B122.4 (2)
O1B—N2B—O2B122.9 (3)N1B—C7B—C8B121.7 (2)
S1B—N3B—C13B121.46 (15)C8B—C7B—C12B115.8 (2)
C13B—N4B—C14B124.8 (2)C7B—C8B—C9B122.1 (2)
C1B—N1B—H12B117.22C8B—C9B—C10B119.6 (2)
C7B—N1B—H12B117.24N2B—C10B—C9B120.1 (2)
C13B—N3B—H16B119.27C9B—C10B—C11B121.0 (2)
S1B—N3B—H16B119.26N2B—C10B—C11B118.9 (2)
C14B—N4B—H17B117.60C10B—C11B—C12B119.5 (2)
C13B—N4B—H17B117.61C7B—C12B—C11B121.67 (19)
N1A—C1A—C2A110.85 (19)S1B—C12B—C7B120.96 (16)
C2A—C1A—C6A111.4 (2)S1B—C12B—C11B117.25 (16)
N1A—C1A—C6A108.60 (18)O5B—C13B—N4B126.4 (2)
C1A—C2A—C3A112.4 (2)O5B—C13B—N3B119.6 (2)
C2A—C3A—C4A111.0 (3)N3B—C13B—N4B114.00 (19)
C3A—C4A—C5A110.9 (3)C16B—C14B—C17B110.3 (2)
C4A—C5A—C6A112.0 (3)N4B—C14B—C15B109.2 (2)
C1A—C6A—C5A111.3 (2)N4B—C14B—C16B109.8 (2)
C8A—C7A—C12A116.1 (2)N4B—C14B—C17B106.1 (2)
N1A—C7A—C8A121.8 (2)C15B—C14B—C16B110.9 (2)
N1A—C7A—C12A122.06 (19)C15B—C14B—C17B110.5 (3)
C7A—C8A—C9A121.7 (2)N1B—C1B—H1B108.78
C8A—C9A—C10A120.5 (2)C2B—C1B—H1B108.80
N2A—C10A—C9A120.5 (2)C6B—C1B—H1B108.75
C9A—C10A—C11A120.4 (2)C1B—C2B—H2B109.47
N2A—C10A—C11A119.1 (2)C1B—C2B—H3B109.44
C10A—C11A—C12A119.6 (2)C3B—C2B—H2B109.47
S1A—C12A—C11A117.60 (16)C3B—C2B—H3B109.42
C7A—C12A—C11A121.57 (19)H2B—C2B—H3B107.97
S1A—C12A—C7A120.72 (16)C2B—C3B—H4B109.32
N3A—C13A—N4A114.77 (18)C2B—C3B—H5B109.35
O5A—C13A—N4A125.5 (2)C4B—C3B—H4B109.32
O5A—C13A—N3A119.70 (19)C4B—C3B—H5B109.35
C15A—C14A—C16A110.6 (2)H4B—C3B—H5B107.98
N4A—C14A—C16A109.55 (17)C3B—C4B—H6B109.16
N4A—C14A—C17A105.6 (2)C3B—C4B—H7B109.18
C16A—C14A—C17A109.8 (2)C5B—C4B—H6B109.24
C15A—C14A—C17A110.0 (2)C5B—C4B—H7B109.26
N4A—C14A—C15A111.07 (19)H6B—C4B—H7B108.06
N1A—C1A—H1A108.68C4B—C5B—H8B109.27
C2A—C1A—H1A108.66C4B—C5B—H9B109.30
C6A—C1A—H1A108.60C6B—C5B—H8B109.38
C1A—C2A—H3A109.16C6B—C5B—H9B109.39
C3A—C2A—H2A109.09H8B—C5B—H9B107.92
C1A—C2A—H2A109.11C1B—C6B—H10B109.59
C3A—C2A—H3A109.15C1B—C6B—H11B109.59
H2A—C2A—H3A107.83C5B—C6B—H10B109.68
C2A—C3A—H4A109.40C5B—C6B—H11B109.59
H4A—C3A—H5A108.04H10B—C6B—H11B108.09
C2A—C3A—H5A109.41C7B—C8B—H13B118.97
C4A—C3A—H4A109.46C9B—C8B—H13B118.90
C4A—C3A—H5A109.47C8B—C9B—H14B120.16
C3A—C4A—H6A109.50C10B—C9B—H14B120.20
C3A—C4A—H7A109.43C10B—C11B—H15B120.30
C5A—C4A—H6A109.40C12B—C11B—H15B120.23
H6A—C4A—H7A108.04C14B—C15B—H18B109.50
C5A—C4A—H7A109.47C14B—C15B—H19B109.49
C6A—C5A—H8A109.26C14B—C15B—H20B109.46
C4A—C5A—H9A109.31H18B—C15B—H19B109.57
H8A—C5A—H9A107.85H18B—C15B—H20B109.36
C6A—C5A—H9A109.20H19B—C15B—H20B109.44
C4A—C5A—H8A109.18C14B—C16B—H21B109.44
H10A—C6A—H11A107.97C14B—C16B—H22B109.49
C5A—C6A—H11A109.42C14B—C16B—H23B109.50
C1A—C6A—H10A109.35H21B—C16B—H22B109.51
C1A—C6A—H11A109.41H21B—C16B—H23B109.45
C5A—C6A—H10A109.33H22B—C16B—H23B109.44
C7A—C8A—H13A119.18C14B—C17B—H24B109.43
C9A—C8A—H13A119.16C14B—C17B—H25B109.44
C10A—C9A—H14A119.68C14B—C17B—H26B109.46
C8A—C9A—H14A119.79H24B—C17B—H25B109.48
C12A—C11A—H15A120.21H24B—C17B—H26B109.49
C10A—C11A—H15A120.23H25B—C17B—H26B109.52
O3A—S1A—N3A—C13A55.56 (18)C13B—N4B—C14B—C15B57.6 (3)
O4A—S1A—N3A—C13A176.33 (16)C13B—N4B—C14B—C16B64.1 (3)
C12A—S1A—N3A—C13A60.45 (18)C14B—N4B—C13B—N3B178.0 (2)
N3A—S1A—C12A—C7A63.76 (19)N1A—C1A—C2A—C3A174.8 (2)
O3A—S1A—C12A—C11A3.9 (2)C2A—C1A—C6A—C5A53.1 (3)
O4A—S1A—C12A—C11A135.93 (17)N1A—C1A—C6A—C5A175.5 (2)
N3A—S1A—C12A—C11A112.41 (18)C6A—C1A—C2A—C3A53.8 (3)
O3A—S1A—C12A—C7A179.9 (2)C1A—C2A—C3A—C4A55.0 (4)
O4A—S1A—C12A—C7A47.9 (2)C2A—C3A—C4A—C5A55.4 (4)
O4B—S1B—N3B—C13B172.36 (16)C3A—C4A—C5A—C6A55.9 (4)
C12B—S1B—N3B—C13B57.54 (18)C4A—C5A—C6A—C1A54.7 (3)
O3B—S1B—C12B—C11B3.4 (2)C12A—C7A—C8A—C9A3.6 (3)
O4B—S1B—C12B—C11B135.12 (17)C8A—C7A—C12A—S1A171.26 (16)
N3B—S1B—C12B—C11B113.38 (17)N1A—C7A—C12A—S1A8.5 (3)
N3B—S1B—C12B—C7B62.8 (2)C8A—C7A—C12A—C11A4.7 (3)
O3B—S1B—N3B—C13B58.42 (19)N1A—C7A—C12A—C11A175.5 (2)
O4B—S1B—C12B—C7B48.7 (2)N1A—C7A—C8A—C9A176.6 (2)
O3B—S1B—C12B—C7B179.55 (17)C7A—C8A—C9A—C10A0.0 (4)
C1A—N1A—C7A—C12A167.5 (2)C8A—C9A—C10A—N2A178.2 (2)
C7A—N1A—C1A—C2A80.9 (3)C8A—C9A—C10A—C11A2.8 (4)
C7A—N1A—C1A—C6A156.4 (2)C9A—C10A—C11A—C12A1.7 (4)
C1A—N1A—C7A—C8A12.2 (3)N2A—C10A—C11A—C12A179.3 (2)
O1A—N2A—C10A—C11A168.7 (2)C10A—C11A—C12A—S1A173.91 (18)
O2A—N2A—C10A—C9A169.8 (3)C10A—C11A—C12A—C7A2.2 (3)
O1A—N2A—C10A—C9A10.3 (4)C2B—C1B—C6B—C5B57.2 (3)
O2A—N2A—C10A—C11A11.2 (4)N1B—C1B—C6B—C5B179.0 (3)
S1A—N3A—C13A—O5A0.8 (3)C6B—C1B—C2B—C3B56.9 (4)
S1A—N3A—C13A—N4A179.76 (14)N1B—C1B—C2B—C3B178.3 (3)
C14A—N4A—C13A—O5A6.8 (4)C1B—C2B—C3B—C4B55.3 (4)
C13A—N4A—C14A—C16A61.9 (3)C2B—C3B—C4B—C5B54.1 (5)
C13A—N4A—C14A—C15A60.7 (3)C3B—C4B—C5B—C6B54.8 (5)
C14A—N4A—C13A—N3A174.25 (18)C4B—C5B—C6B—C1B56.0 (4)
C13A—N4A—C14A—C17A179.9 (3)N1B—C7B—C8B—C9B174.1 (2)
C7B—N1B—C1B—C6B157.0 (2)N1B—C7B—C12B—S1B8.8 (3)
C7B—N1B—C1B—C2B81.0 (3)C12B—C7B—C8B—C9B5.3 (3)
C1B—N1B—C7B—C12B168.2 (2)N1B—C7B—C12B—C11B175.2 (2)
C1B—N1B—C7B—C8B12.4 (4)C8B—C7B—C12B—S1B171.80 (17)
O1B—N2B—C10B—C11B179.0 (2)C8B—C7B—C12B—C11B4.2 (3)
O2B—N2B—C10B—C9B179.5 (2)C7B—C8B—C9B—C10B2.1 (4)
O1B—N2B—C10B—C9B0.4 (4)C8B—C9B—C10B—C11B2.5 (4)
O2B—N2B—C10B—C11B2.0 (4)C8B—C9B—C10B—N2B179.0 (2)
S1B—N3B—C13B—O5B6.7 (3)N2B—C10B—C11B—C12B177.9 (2)
S1B—N3B—C13B—N4B172.15 (15)C9B—C10B—C11B—C12B3.5 (3)
C13B—N4B—C14B—C17B176.7 (2)C10B—C11B—C12B—C7B0.0 (3)
C14B—N4B—C13B—O5B3.3 (4)C10B—C11B—C12B—S1B176.16 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H12A···O4A0.862.222.919 (3)139
N1B—H12B···O4B0.862.252.935 (3)137
N3A—H16A···O3B0.862.313.094 (3)153
N3B—H16B···O3Ai0.862.293.045 (3)147
N3B—H16B···O5Ai0.862.603.252 (3)134
N4A—H17A···O5B0.862.212.936 (3)142
N4B—H17B···O5Ai0.862.202.893 (3)137
C2B—H2B···O1Bii0.972.503.457 (4)168
C11A—H15A···O3A0.932.442.843 (3)107
C11B—H15B···O3B0.932.432.837 (3)107
C15A—H19A···O5A0.962.423.022 (4)121
C15B—H19B···O5B0.962.403.002 (5)120
C16A—H21A···O5A0.962.553.109 (3)117
C16B—H21B···O5B0.962.573.154 (4)119
C16A—H22A···O4Biii0.962.553.414 (3)150
C16B—H22B···O4Aiv0.962.593.399 (3)142
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x, y, z; (iii) x, y+1, z; (iv) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H26N4O5S
Mr398.49
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)14.447 (5), 11.579 (5), 24.981 (5)
β (°) 95.195 (5)
V3)4162 (2)
Z8
Radiation typeCu Kα
µ (mm1)1.68
Crystal size (mm)0.42 × 0.17 × 0.13
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionAnalytical
(de Meulenaer & Tompa, 1965)
Tmin, Tmax0.539, 0.811
No. of measured, independent and
observed [I > 2σ(I)] reflections
11170, 8166, 5832
Rint0.018
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.136, 1.04
No. of reflections8166
No. of parameters487
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.51

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, HELENA (Spek, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990), SHELXL97.

Selected torsion angles (º) top
O1A—N2A—C10A—C11A168.7 (2)O1B—N2B—C10B—C11B179.0 (2)
O2A—N2A—C10A—C9A169.8 (3)O2B—N2B—C10B—C9B179.5 (2)
O1A—N2A—C10A—C9A10.3 (4)O1B—N2B—C10B—C9B0.4 (4)
O2A—N2A—C10A—C11A11.2 (4)O2B—N2B—C10B—C11B2.0 (4)
S1A—N3A—C13A—N4A179.76 (14)S1B—N3B—C13B—N4B172.15 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H12A···O4A0.862.222.919 (3)139
N1B—H12B···O4B0.862.252.935 (3)137
N3A—H16A···O3B0.862.313.094 (3)153
N3B—H16B···O3Ai0.862.293.045 (3)147
N3B—H16B···O5Ai0.862.603.252 (3)134
N4A—H17A···O5B0.862.212.936 (3)142
N4B—H17B···O5Ai0.862.202.893 (3)137
C2B—H2B···O1Bii0.972.503.457 (4)168
C15A—H19A···O5A0.962.423.022 (4)121
C15B—H19B···O5B0.962.403.002 (5)120
C16A—H21A···O5A0.962.553.109 (3)117
C16B—H21B···O5B0.962.573.154 (4)119
C16A—H22A···O4Biii0.962.553.414 (3)150
C16B—H22B···O4Aiv0.962.593.399 (3)142
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x, y, z; (iii) x, y+1, z; (iv) x+1/2, y+1/2, z+1/2.
Theoretical torsion angles (°) along the sulfonylurea group for the α, β, γ, δ and ε conformations top
conformerϕ1 (1-2-3-4)ϕ2 (2-3-4-5)ϕ3 (3-4-5-6)ϕ4 (4-5-6-7)
α-9090180180
β90901800
γ9090180180
δ90900180
ε-90-90180180
Torsion angles (°) for the ε conformation of the two asymmetric molecules of (I) top
ϕ1ϕ2ϕ3ϕ4
molecule A-63.75 (19)-60.5 (2)179.7 (1)174.3 (2)
molecule B-62.8 (2)-57.5 (2)172.2 (1)178.3 (2)
 

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