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
CCDC reference: 197343
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.
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.
N-
tert-Butyl-
N'-[(2-cyclohexylamino-5-nitrobenzene)sulfonyl]urea
top
Crystal data top
C17H26N4O5S | F(000) = 1696 |
Mr = 398.49 | Dx = 1.272 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P2yn | Cell parameters from 25 reflections |
a = 14.447 (5) Å | θ = 30–40° |
b = 11.579 (5) Å | µ = 1.68 mm−1 |
c = 24.981 (5) Å | T = 293 K |
β = 95.195 (5)° | Polyhedral, colourless |
V = 4162 (2) Å3 | 0.42 × 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 tube | Rint = 0.018 |
Graphite monochromator | θmax = 71.9°, θmin = 3.4° |
θ/2θ scans | h = −17→12 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = 0→14 |
Tmin = 0.539, Tmax = 0.811 | l = −30→30 |
11170 measured reflections | 3 standard reflections every 200 reflections |
8166 independent reflections | intensity decay: 5% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-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 parameters | Δρmax = 0.21 e Å−3 |
6 restraints | Δρmin = −0.51 e Å−3 |
Crystal data top
C17H26N4O5S | V = 4162 (2) Å3 |
Mr = 398.49 | Z = 8 |
Monoclinic, P21/n | Cu Kα radiation |
a = 14.447 (5) Å | µ = 1.68 mm−1 |
b = 11.579 (5) Å | T = 293 K |
c = 24.981 (5) Å | 0.42 × 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 = 0.811 | 3 standard reflections every 200 reflections |
11170 measured reflections | intensity decay: 5% |
8166 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 6 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.21 e Å−3 |
8166 reflections | Δρmin = −0.51 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1A | 0.46669 (4) | −0.02237 (5) | 0.24699 (2) | 0.0466 (2) | |
O1A | 0.80450 (16) | 0.2815 (2) | 0.20364 (13) | 0.1230 (13) | |
O2A | 0.74021 (18) | 0.2673 (2) | 0.27740 (13) | 0.1237 (11) | |
O3A | 0.46468 (11) | 0.04913 (14) | 0.29378 (6) | 0.0599 (6) | |
O4A | 0.46019 (11) | −0.14478 (13) | 0.25245 (6) | 0.0589 (6) | |
O5A | 0.41749 (10) | 0.20065 (13) | 0.20135 (7) | 0.0611 (5) | |
N1A | 0.53714 (13) | −0.13700 (16) | 0.14839 (7) | 0.0564 (7) | |
N2A | 0.74950 (16) | 0.2366 (2) | 0.23159 (14) | 0.0877 (12) | |
N3A | 0.37813 (11) | 0.01102 (15) | 0.20431 (7) | 0.0491 (6) | |
N4A | 0.28812 (13) | 0.13824 (16) | 0.15100 (8) | 0.0585 (7) | |
C1A | 0.53941 (15) | −0.1894 (2) | 0.09529 (9) | 0.0537 (8) | |
C2A | 0.4778 (2) | −0.1241 (2) | 0.05376 (11) | 0.0714 (10) | |
C3A | 0.4715 (3) | −0.1823 (3) | −0.00108 (12) | 0.0958 (15) | |
C4A | 0.4403 (3) | −0.3062 (3) | 0.00271 (13) | 0.0974 (16) | |
C5A | 0.5032 (2) | −0.3720 (3) | 0.04342 (12) | 0.0878 (11) | |
C6A | 0.5098 (2) | −0.3147 (2) | 0.09853 (10) | 0.0684 (9) | |
C7A | 0.58536 (14) | −0.04404 (19) | 0.16714 (9) | 0.0479 (7) | |
C8A | 0.65903 (16) | 0.0024 (2) | 0.14019 (10) | 0.0638 (9) | |
C9A | 0.71074 (17) | 0.0927 (2) | 0.16067 (12) | 0.0696 (10) | |
C10A | 0.69264 (16) | 0.1424 (2) | 0.20900 (11) | 0.0616 (8) | |
C11A | 0.61940 (14) | 0.1041 (2) | 0.23583 (10) | 0.0542 (7) | |
C12A | 0.56534 (14) | 0.01352 (18) | 0.21489 (8) | 0.0454 (6) | |
C13A | 0.36302 (14) | 0.12446 (19) | 0.18585 (9) | 0.0482 (7) | |
C14A | 0.25455 (13) | 0.25131 (19) | 0.13039 (8) | 0.0613 (8) | |
C15A | 0.3278 (2) | 0.3117 (3) | 0.10019 (13) | 0.1011 (16) | |
C16A | 0.2279 (2) | 0.3258 (2) | 0.17688 (10) | 0.0748 (10) | |
C17A | 0.1687 (2) | 0.2257 (3) | 0.09223 (16) | 0.1209 (17) | |
S1B | 0.21534 (3) | −0.27040 (5) | 0.13474 (2) | 0.0478 (2) | |
O1B | 0.15411 (18) | 0.0460 (2) | −0.06604 (9) | 0.1022 (10) | |
O2B | 0.27329 (18) | 0.0384 (2) | −0.00824 (9) | 0.0985 (9) | |
O3B | 0.29995 (10) | −0.20668 (15) | 0.14425 (7) | 0.0635 (6) | |
O4B | 0.21782 (11) | −0.39360 (13) | 0.13476 (7) | 0.0612 (6) | |
O5B | 0.15095 (13) | −0.04467 (13) | 0.16326 (7) | 0.0679 (6) | |
N1B | 0.03366 (13) | −0.36284 (18) | 0.07664 (8) | 0.0618 (7) | |
N2B | 0.19627 (19) | 0.0056 (2) | −0.02550 (9) | 0.0726 (9) | |
N3B | 0.14646 (12) | −0.23777 (15) | 0.18043 (7) | 0.0495 (6) | |
N4B | 0.05295 (13) | −0.11285 (16) | 0.22201 (8) | 0.0565 (6) | |
C1B | −0.06215 (17) | −0.4043 (2) | 0.06522 (10) | 0.0672 (9) | |
C2B | −0.12715 (19) | −0.3358 (3) | 0.09666 (14) | 0.0865 (13) | |
C3B | −0.2267 (2) | −0.3803 (4) | 0.0865 (2) | 0.124 (2) | |
C4B | −0.2325 (2) | −0.5068 (4) | 0.09838 (17) | 0.1114 (16) | |
C5B | −0.1664 (3) | −0.5758 (4) | 0.06833 (18) | 0.1183 (17) | |
C6B | −0.0669 (2) | −0.5317 (3) | 0.07904 (14) | 0.0868 (11) | |
C7B | 0.07040 (15) | −0.2698 (2) | 0.05421 (9) | 0.0514 (7) | |
C8B | 0.02456 (18) | −0.2138 (2) | 0.00885 (10) | 0.0661 (9) | |
C9B | 0.06481 (18) | −0.1259 (2) | −0.01700 (10) | 0.0661 (9) | |
C10B | 0.15207 (17) | −0.0867 (2) | 0.00223 (9) | 0.0556 (8) | |
C11B | 0.19740 (15) | −0.13206 (19) | 0.04822 (8) | 0.0506 (7) | |
C12B | 0.15755 (14) | −0.22224 (19) | 0.07399 (8) | 0.0460 (7) | |
C13B | 0.11742 (16) | −0.12309 (19) | 0.18804 (8) | 0.0508 (7) | |
C14B | 0.01291 (19) | −0.0021 (2) | 0.23828 (11) | 0.0676 (9) | |
C15B | −0.0299 (3) | 0.0616 (3) | 0.18795 (14) | 0.1151 (17) | |
C16B | 0.0878 (2) | 0.0705 (2) | 0.26841 (12) | 0.0825 (11) | |
C17B | −0.0621 (2) | −0.0333 (3) | 0.27495 (16) | 0.1103 (16) | |
H1A | 0.60340 | −0.18690 | 0.08520 | 0.0640* | |
H2A | 0.50200 | −0.04650 | 0.05050 | 0.0860* | |
H3A | 0.41600 | −0.11790 | 0.06570 | 0.0860* | |
H4A | 0.42780 | −0.14050 | −0.02570 | 0.1150* | |
H5A | 0.53180 | −0.17990 | −0.01520 | 0.1150* | |
H6A | 0.37720 | −0.30830 | 0.01300 | 0.1170* | |
H7A | 0.44070 | −0.34280 | −0.03220 | 0.1170* | |
H8A | 0.47970 | −0.45000 | 0.04640 | 0.1060* | |
H9A | 0.56480 | −0.37700 | 0.03110 | 0.1060* | |
H10A | 0.44980 | −0.31870 | 0.11300 | 0.0820* | |
H11A | 0.55440 | −0.35620 | 0.12280 | 0.0820* | |
H12A | 0.50130 | −0.16890 | 0.16980 | 0.0680* | |
H13A | 0.67230 | −0.02970 | 0.10760 | 0.0770* | |
H14A | 0.75870 | 0.12140 | 0.14210 | 0.0840* | |
H15A | 0.60640 | 0.13890 | 0.26790 | 0.0650* | |
H16A | 0.33990 | −0.04230 | 0.19290 | 0.0590* | |
H17A | 0.25770 | 0.07760 | 0.14000 | 0.0700* | |
H18A | 0.34260 | 0.26450 | 0.07060 | 0.1520* | |
H19A | 0.38280 | 0.32400 | 0.12410 | 0.1520* | |
H20A | 0.30410 | 0.38480 | 0.08690 | 0.1520* | |
H21A | 0.28250 | 0.34270 | 0.20040 | 0.1120* | |
H22A | 0.20060 | 0.39650 | 0.16310 | 0.1120* | |
H23A | 0.18400 | 0.28490 | 0.19640 | 0.1120* | |
H24A | 0.14380 | 0.29660 | 0.07710 | 0.1820* | |
H25A | 0.12270 | 0.18820 | 0.11160 | 0.1820* | |
H26A | 0.18540 | 0.17600 | 0.06390 | 0.1820* | |
H1B | −0.08070 | −0.39450 | 0.02680 | 0.0810* | |
H2B | −0.12500 | −0.25520 | 0.08640 | 0.1040* | |
H3B | −0.10720 | −0.34130 | 0.13470 | 0.1040* | |
H4B | −0.26640 | −0.33810 | 0.10900 | 0.1480* | |
H5B | −0.24910 | −0.36650 | 0.04930 | 0.1480* | |
H6B | −0.21840 | −0.51910 | 0.13670 | 0.1340* | |
H7B | −0.29540 | −0.53340 | 0.08860 | 0.1340* | |
H8B | −0.16900 | −0.65610 | 0.07910 | 0.1420* | |
H9B | −0.18530 | −0.57150 | 0.03010 | 0.1420* | |
H10B | −0.04550 | −0.54310 | 0.11660 | 0.1040* | |
H11B | −0.02640 | −0.57510 | 0.05750 | 0.1040* | |
H12B | 0.06930 | −0.40130 | 0.09960 | 0.0740* | |
H13B | −0.03490 | −0.23770 | −0.00370 | 0.0790* | |
H14B | 0.03380 | −0.09250 | −0.04740 | 0.0790* | |
H15B | 0.25450 | −0.10220 | 0.06190 | 0.0610* | |
H16B | 0.12730 | −0.29160 | 0.20040 | 0.0590* | |
H17B | 0.03280 | −0.17520 | 0.23570 | 0.0680* | |
H18B | −0.07600 | 0.01340 | 0.16900 | 0.1720* | |
H19B | 0.01790 | 0.07940 | 0.16500 | 0.1720* | |
H20B | −0.05850 | 0.13190 | 0.19850 | 0.1720* | |
H21B | 0.13680 | 0.08470 | 0.24570 | 0.1240* | |
H22B | 0.06170 | 0.14270 | 0.27850 | 0.1240* | |
H23B | 0.11240 | 0.03010 | 0.30010 | 0.1240* | |
H24B | −0.09400 | 0.03550 | 0.28430 | 0.1660* | |
H25B | −0.03390 | −0.06920 | 0.30700 | 0.1660* | |
H26B | −0.10560 | −0.08580 | 0.25660 | 0.1660* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0467 (3) | 0.0482 (3) | 0.0458 (3) | 0.0011 (2) | 0.0084 (2) | −0.0044 (2) |
O1A | 0.0804 (15) | 0.0921 (17) | 0.200 (3) | −0.0382 (13) | 0.0326 (17) | −0.0196 (17) |
O2A | 0.1056 (19) | 0.121 (2) | 0.143 (2) | −0.0440 (16) | 0.0029 (17) | −0.0544 (18) |
O3A | 0.0632 (10) | 0.0701 (11) | 0.0471 (8) | 0.0009 (8) | 0.0087 (7) | −0.0146 (7) |
O4A | 0.0674 (10) | 0.0473 (9) | 0.0636 (10) | −0.0001 (7) | 0.0149 (8) | 0.0063 (7) |
O5A | 0.0483 (8) | 0.0460 (9) | 0.0863 (11) | −0.0029 (7) | −0.0090 (8) | −0.0100 (8) |
N1A | 0.0611 (11) | 0.0564 (12) | 0.0546 (11) | −0.0079 (9) | 0.0210 (9) | −0.0119 (9) |
N2A | 0.0525 (13) | 0.0707 (16) | 0.139 (3) | −0.0136 (12) | 0.0032 (15) | −0.0199 (17) |
N3A | 0.0409 (9) | 0.0432 (10) | 0.0619 (11) | −0.0022 (7) | −0.0021 (8) | −0.0090 (8) |
N4A | 0.0531 (11) | 0.0513 (11) | 0.0679 (12) | −0.0004 (9) | −0.0123 (9) | −0.0093 (9) |
C1A | 0.0505 (12) | 0.0576 (14) | 0.0545 (13) | 0.0028 (10) | 0.0125 (10) | −0.0109 (11) |
C2A | 0.0814 (18) | 0.0635 (16) | 0.0691 (16) | 0.0048 (14) | 0.0054 (14) | −0.0018 (13) |
C3A | 0.119 (3) | 0.103 (3) | 0.0620 (17) | 0.002 (2) | −0.0099 (17) | −0.0037 (17) |
C4A | 0.105 (3) | 0.105 (3) | 0.079 (2) | −0.008 (2) | −0.0091 (18) | −0.0308 (19) |
C5A | 0.111 (2) | 0.0672 (18) | 0.086 (2) | 0.0013 (17) | 0.0128 (18) | −0.0300 (16) |
C6A | 0.0841 (18) | 0.0545 (15) | 0.0676 (16) | 0.0077 (13) | 0.0121 (13) | −0.0101 (12) |
C7A | 0.0420 (11) | 0.0495 (12) | 0.0527 (12) | 0.0048 (9) | 0.0078 (9) | −0.0028 (10) |
C8A | 0.0529 (13) | 0.0748 (17) | 0.0664 (15) | −0.0051 (12) | 0.0199 (11) | −0.0066 (13) |
C9A | 0.0473 (13) | 0.0736 (17) | 0.0896 (19) | −0.0091 (12) | 0.0155 (12) | 0.0030 (15) |
C10A | 0.0417 (11) | 0.0539 (14) | 0.0883 (18) | −0.0046 (10) | 0.0007 (11) | −0.0052 (13) |
C11A | 0.0443 (11) | 0.0532 (13) | 0.0640 (14) | 0.0039 (10) | −0.0013 (10) | −0.0056 (11) |
C12A | 0.0399 (10) | 0.0464 (12) | 0.0498 (11) | 0.0029 (9) | 0.0039 (8) | −0.0002 (9) |
C13A | 0.0412 (10) | 0.0485 (12) | 0.0546 (12) | 0.0023 (9) | 0.0030 (9) | −0.0118 (10) |
C14A | 0.0592 (14) | 0.0597 (15) | 0.0631 (14) | 0.0066 (11) | −0.0056 (11) | 0.0037 (12) |
C15A | 0.107 (3) | 0.112 (3) | 0.088 (2) | 0.012 (2) | 0.0298 (19) | 0.031 (2) |
C16A | 0.0754 (17) | 0.0619 (16) | 0.0881 (19) | 0.0173 (14) | 0.0132 (15) | 0.0051 (14) |
C17A | 0.114 (3) | 0.097 (3) | 0.136 (3) | 0.012 (2) | −0.074 (2) | 0.001 (2) |
S1B | 0.0413 (3) | 0.0508 (3) | 0.0503 (3) | −0.0022 (2) | −0.0007 (2) | 0.0038 (2) |
O1B | 0.1270 (19) | 0.1012 (17) | 0.0804 (14) | 0.0143 (14) | 0.0204 (13) | 0.0428 (13) |
O2B | 0.1058 (17) | 0.1028 (17) | 0.0889 (15) | −0.0338 (14) | 0.0202 (13) | 0.0223 (13) |
O3B | 0.0408 (8) | 0.0794 (12) | 0.0682 (10) | −0.0133 (8) | −0.0065 (7) | 0.0084 (9) |
O4B | 0.0605 (9) | 0.0485 (9) | 0.0742 (11) | 0.0092 (8) | 0.0032 (8) | 0.0035 (8) |
O5B | 0.0956 (13) | 0.0469 (9) | 0.0626 (10) | −0.0141 (9) | 0.0148 (9) | 0.0031 (8) |
N1B | 0.0561 (11) | 0.0637 (13) | 0.0624 (12) | −0.0156 (10) | −0.0122 (9) | 0.0064 (10) |
N2B | 0.0915 (17) | 0.0703 (15) | 0.0595 (13) | 0.0031 (13) | 0.0262 (12) | 0.0121 (11) |
N3B | 0.0602 (11) | 0.0430 (10) | 0.0459 (9) | −0.0065 (8) | 0.0078 (8) | 0.0023 (8) |
N4B | 0.0611 (11) | 0.0476 (11) | 0.0611 (11) | −0.0028 (9) | 0.0076 (9) | −0.0034 (9) |
C1B | 0.0571 (14) | 0.0823 (19) | 0.0598 (14) | −0.0204 (13) | −0.0086 (11) | 0.0039 (13) |
C2B | 0.0623 (17) | 0.0740 (19) | 0.121 (3) | 0.0021 (15) | −0.0035 (16) | 0.0076 (18) |
C3B | 0.0594 (19) | 0.131 (4) | 0.179 (4) | 0.000 (2) | 0.003 (2) | 0.025 (3) |
C4B | 0.066 (2) | 0.132 (3) | 0.137 (3) | −0.030 (2) | 0.014 (2) | 0.007 (3) |
C5B | 0.098 (3) | 0.118 (3) | 0.140 (3) | −0.058 (2) | 0.016 (2) | −0.029 (3) |
C6B | 0.0783 (19) | 0.075 (2) | 0.108 (2) | −0.0230 (16) | 0.0139 (17) | −0.0236 (17) |
C7B | 0.0516 (12) | 0.0548 (13) | 0.0468 (11) | −0.0027 (10) | −0.0013 (9) | −0.0035 (10) |
C8B | 0.0598 (14) | 0.0790 (18) | 0.0564 (14) | −0.0076 (13) | −0.0122 (11) | 0.0022 (13) |
C9B | 0.0729 (17) | 0.0752 (18) | 0.0485 (13) | 0.0055 (14) | −0.0043 (11) | 0.0077 (12) |
C10B | 0.0693 (15) | 0.0532 (13) | 0.0460 (12) | 0.0036 (11) | 0.0150 (11) | 0.0023 (10) |
C11B | 0.0510 (12) | 0.0553 (13) | 0.0463 (11) | −0.0017 (10) | 0.0083 (9) | −0.0025 (10) |
C12B | 0.0447 (11) | 0.0502 (12) | 0.0431 (11) | 0.0006 (9) | 0.0032 (8) | −0.0022 (9) |
C13B | 0.0591 (13) | 0.0474 (12) | 0.0441 (11) | −0.0081 (10) | −0.0050 (10) | −0.0026 (9) |
C14B | 0.0707 (16) | 0.0596 (15) | 0.0712 (16) | 0.0133 (12) | −0.0007 (13) | −0.0083 (12) |
C15B | 0.117 (3) | 0.119 (3) | 0.103 (3) | 0.057 (2) | −0.025 (2) | 0.001 (2) |
C16B | 0.103 (2) | 0.0560 (16) | 0.086 (2) | 0.0037 (15) | −0.0051 (17) | −0.0179 (14) |
C17B | 0.092 (2) | 0.108 (3) | 0.137 (3) | −0.001 (2) | 0.044 (2) | −0.036 (2) |
Geometric parameters (Å, º) top
S1A—O3A | 1.4348 (17) | C5A—H9A | 0.9694 |
S1A—O4A | 1.4278 (17) | C5A—H8A | 0.9701 |
S1A—N3A | 1.6359 (19) | C6A—H10A | 0.9700 |
S1A—C12A | 1.748 (2) | C6A—H11A | 0.9710 |
S1B—C12B | 1.755 (2) | C8A—H13A | 0.9306 |
S1B—O3B | 1.4291 (17) | C9A—H14A | 0.9295 |
S1B—O4B | 1.4270 (17) | C11A—H15A | 0.9310 |
S1B—N3B | 1.6252 (19) | C15A—H19A | 0.9605 |
O1A—N2A | 1.221 (4) | C15A—H20A | 0.9609 |
O2A—N2A | 1.217 (5) | C15A—H18A | 0.9589 |
O5A—C13A | 1.222 (3) | C16A—H22A | 0.9590 |
O1B—N2B | 1.226 (3) | C16A—H23A | 0.9593 |
O2B—N2B | 1.217 (4) | C16A—H21A | 0.9601 |
O5B—C13B | 1.223 (3) | C17A—H24A | 0.9600 |
N1A—C1A | 1.462 (3) | C17A—H25A | 0.9605 |
N1A—C7A | 1.343 (3) | C17A—H26A | 0.9598 |
N2A—C10A | 1.449 (4) | C1B—C6B | 1.518 (4) |
N3A—C13A | 1.403 (3) | C1B—C2B | 1.504 (4) |
N4A—C13A | 1.336 (3) | C2B—C3B | 1.527 (4) |
N4A—C14A | 1.473 (3) | C3B—C4B | 1.498 (7) |
N1A—H12A | 0.8607 | C4B—C5B | 1.498 (6) |
N3A—H16A | 0.8596 | C5B—C6B | 1.526 (5) |
N4A—H17A | 0.8601 | C7B—C8B | 1.417 (3) |
N1B—C1B | 1.468 (3) | C7B—C12B | 1.421 (3) |
N1B—C7B | 1.345 (3) | C8B—C9B | 1.363 (3) |
N2B—C10B | 1.453 (3) | C9B—C10B | 1.384 (4) |
N3B—C13B | 1.411 (3) | C10B—C11B | 1.374 (3) |
N4B—C13B | 1.321 (3) | C11B—C12B | 1.380 (3) |
N4B—C14B | 1.479 (3) | C14B—C15B | 1.538 (5) |
N1B—H12B | 0.8596 | C14B—C16B | 1.515 (4) |
N3B—H16B | 0.8597 | C14B—C17B | 1.524 (4) |
N4B—H17B | 0.8608 | C1B—H1B | 0.9794 |
C1A—C2A | 1.508 (4) | C2B—H2B | 0.9691 |
C1A—C6A | 1.517 (3) | C2B—H3B | 0.9698 |
C2A—C3A | 1.522 (4) | C3B—H4B | 0.9706 |
C3A—C4A | 1.509 (5) | C3B—H5B | 0.9692 |
C4A—C5A | 1.508 (5) | C4B—H6B | 0.9710 |
C5A—C6A | 1.523 (4) | C4B—H7B | 0.9696 |
C7A—C12A | 1.419 (3) | C5B—H8B | 0.9696 |
C7A—C8A | 1.416 (3) | C5B—H9B | 0.9705 |
C8A—C9A | 1.358 (3) | C6B—H10B | 0.9700 |
C9A—C10A | 1.384 (4) | C6B—H11B | 0.9703 |
C10A—C11A | 1.376 (3) | C8B—H13B | 0.9295 |
C11A—C12A | 1.382 (3) | C9B—H14B | 0.9303 |
C14A—C15A | 1.524 (4) | C11B—H15B | 0.9305 |
C14A—C16A | 1.524 (3) | C15B—H18B | 0.9602 |
C14A—C17A | 1.523 (4) | C15B—H19B | 0.9590 |
C1A—H1A | 0.9804 | C15B—H20B | 0.9605 |
C2A—H2A | 0.9702 | C16B—H21B | 0.9606 |
C2A—H3A | 0.9693 | C16B—H22B | 0.9601 |
C3A—H4A | 0.9699 | C16B—H23B | 0.9596 |
C3A—H5A | 0.9694 | C17B—H24B | 0.9597 |
C4A—H7A | 0.9701 | C17B—H25B | 0.9595 |
C4A—H6A | 0.9696 | C17B—H26B | 0.9604 |
| | | |
O3A—S1A—O4A | 119.25 (9) | C14A—C15A—H18A | 109.48 |
O3A—S1A—N3A | 108.80 (9) | H18A—C15A—H19A | 109.53 |
O3A—S1A—C12A | 108.31 (10) | H19A—C15A—H20A | 109.46 |
O4A—S1A—N3A | 104.04 (9) | H18A—C15A—H20A | 109.46 |
O4A—S1A—C12A | 110.08 (10) | C14A—C15A—H20A | 109.48 |
N3A—S1A—C12A | 105.48 (9) | C14A—C15A—H19A | 109.43 |
O3B—S1B—N3B | 109.40 (10) | C14A—C16A—H21A | 109.36 |
O3B—S1B—C12B | 108.20 (10) | H21A—C16A—H22A | 109.52 |
O4B—S1B—N3B | 104.42 (10) | H21A—C16A—H23A | 109.51 |
O4B—S1B—C12B | 109.14 (10) | C14A—C16A—H23A | 109.41 |
N3B—S1B—C12B | 105.06 (9) | C14A—C16A—H22A | 109.49 |
O3B—S1B—O4B | 119.67 (10) | H22A—C16A—H23A | 109.54 |
C1A—N1A—C7A | 126.55 (19) | C14A—C17A—H25A | 109.51 |
O1A—N2A—O2A | 123.1 (3) | H24A—C17A—H26A | 109.43 |
O2A—N2A—C10A | 118.6 (3) | H25A—C17A—H26A | 109.39 |
O1A—N2A—C10A | 118.3 (3) | C14A—C17A—H24A | 109.56 |
S1A—N3A—C13A | 121.66 (14) | C14A—C17A—H26A | 109.47 |
C13A—N4A—C14A | 123.77 (18) | H24A—C17A—H25A | 109.47 |
C1A—N1A—H12A | 116.74 | N1B—C1B—C2B | 110.4 (2) |
C7A—N1A—H12A | 116.71 | C2B—C1B—C6B | 110.5 (2) |
S1A—N3A—H16A | 119.17 | N1B—C1B—C6B | 109.6 (2) |
C13A—N3A—H16A | 119.17 | C1B—C2B—C3B | 111.0 (3) |
C14A—N4A—H17A | 118.13 | C2B—C3B—C4B | 111.4 (3) |
C13A—N4A—H17A | 118.11 | C3B—C4B—C5B | 111.9 (3) |
C1B—N1B—C7B | 125.5 (2) | C4B—C5B—C6B | 111.5 (3) |
O1B—N2B—C10B | 117.9 (2) | C1B—C6B—C5B | 110.3 (3) |
O2B—N2B—C10B | 119.2 (2) | N1B—C7B—C12B | 122.4 (2) |
O1B—N2B—O2B | 122.9 (3) | N1B—C7B—C8B | 121.7 (2) |
S1B—N3B—C13B | 121.46 (15) | C8B—C7B—C12B | 115.8 (2) |
C13B—N4B—C14B | 124.8 (2) | C7B—C8B—C9B | 122.1 (2) |
C1B—N1B—H12B | 117.22 | C8B—C9B—C10B | 119.6 (2) |
C7B—N1B—H12B | 117.24 | N2B—C10B—C9B | 120.1 (2) |
C13B—N3B—H16B | 119.27 | C9B—C10B—C11B | 121.0 (2) |
S1B—N3B—H16B | 119.26 | N2B—C10B—C11B | 118.9 (2) |
C14B—N4B—H17B | 117.60 | C10B—C11B—C12B | 119.5 (2) |
C13B—N4B—H17B | 117.61 | C7B—C12B—C11B | 121.67 (19) |
N1A—C1A—C2A | 110.85 (19) | S1B—C12B—C7B | 120.96 (16) |
C2A—C1A—C6A | 111.4 (2) | S1B—C12B—C11B | 117.25 (16) |
N1A—C1A—C6A | 108.60 (18) | O5B—C13B—N4B | 126.4 (2) |
C1A—C2A—C3A | 112.4 (2) | O5B—C13B—N3B | 119.6 (2) |
C2A—C3A—C4A | 111.0 (3) | N3B—C13B—N4B | 114.00 (19) |
C3A—C4A—C5A | 110.9 (3) | C16B—C14B—C17B | 110.3 (2) |
C4A—C5A—C6A | 112.0 (3) | N4B—C14B—C15B | 109.2 (2) |
C1A—C6A—C5A | 111.3 (2) | N4B—C14B—C16B | 109.8 (2) |
C8A—C7A—C12A | 116.1 (2) | N4B—C14B—C17B | 106.1 (2) |
N1A—C7A—C8A | 121.8 (2) | C15B—C14B—C16B | 110.9 (2) |
N1A—C7A—C12A | 122.06 (19) | C15B—C14B—C17B | 110.5 (3) |
C7A—C8A—C9A | 121.7 (2) | N1B—C1B—H1B | 108.78 |
C8A—C9A—C10A | 120.5 (2) | C2B—C1B—H1B | 108.80 |
N2A—C10A—C9A | 120.5 (2) | C6B—C1B—H1B | 108.75 |
C9A—C10A—C11A | 120.4 (2) | C1B—C2B—H2B | 109.47 |
N2A—C10A—C11A | 119.1 (2) | C1B—C2B—H3B | 109.44 |
C10A—C11A—C12A | 119.6 (2) | C3B—C2B—H2B | 109.47 |
S1A—C12A—C11A | 117.60 (16) | C3B—C2B—H3B | 109.42 |
C7A—C12A—C11A | 121.57 (19) | H2B—C2B—H3B | 107.97 |
S1A—C12A—C7A | 120.72 (16) | C2B—C3B—H4B | 109.32 |
N3A—C13A—N4A | 114.77 (18) | C2B—C3B—H5B | 109.35 |
O5A—C13A—N4A | 125.5 (2) | C4B—C3B—H4B | 109.32 |
O5A—C13A—N3A | 119.70 (19) | C4B—C3B—H5B | 109.35 |
C15A—C14A—C16A | 110.6 (2) | H4B—C3B—H5B | 107.98 |
N4A—C14A—C16A | 109.55 (17) | C3B—C4B—H6B | 109.16 |
N4A—C14A—C17A | 105.6 (2) | C3B—C4B—H7B | 109.18 |
C16A—C14A—C17A | 109.8 (2) | C5B—C4B—H6B | 109.24 |
C15A—C14A—C17A | 110.0 (2) | C5B—C4B—H7B | 109.26 |
N4A—C14A—C15A | 111.07 (19) | H6B—C4B—H7B | 108.06 |
N1A—C1A—H1A | 108.68 | C4B—C5B—H8B | 109.27 |
C2A—C1A—H1A | 108.66 | C4B—C5B—H9B | 109.30 |
C6A—C1A—H1A | 108.60 | C6B—C5B—H8B | 109.38 |
C1A—C2A—H3A | 109.16 | C6B—C5B—H9B | 109.39 |
C3A—C2A—H2A | 109.09 | H8B—C5B—H9B | 107.92 |
C1A—C2A—H2A | 109.11 | C1B—C6B—H10B | 109.59 |
C3A—C2A—H3A | 109.15 | C1B—C6B—H11B | 109.59 |
H2A—C2A—H3A | 107.83 | C5B—C6B—H10B | 109.68 |
C2A—C3A—H4A | 109.40 | C5B—C6B—H11B | 109.59 |
H4A—C3A—H5A | 108.04 | H10B—C6B—H11B | 108.09 |
C2A—C3A—H5A | 109.41 | C7B—C8B—H13B | 118.97 |
C4A—C3A—H4A | 109.46 | C9B—C8B—H13B | 118.90 |
C4A—C3A—H5A | 109.47 | C8B—C9B—H14B | 120.16 |
C3A—C4A—H6A | 109.50 | C10B—C9B—H14B | 120.20 |
C3A—C4A—H7A | 109.43 | C10B—C11B—H15B | 120.30 |
C5A—C4A—H6A | 109.40 | C12B—C11B—H15B | 120.23 |
H6A—C4A—H7A | 108.04 | C14B—C15B—H18B | 109.50 |
C5A—C4A—H7A | 109.47 | C14B—C15B—H19B | 109.49 |
C6A—C5A—H8A | 109.26 | C14B—C15B—H20B | 109.46 |
C4A—C5A—H9A | 109.31 | H18B—C15B—H19B | 109.57 |
H8A—C5A—H9A | 107.85 | H18B—C15B—H20B | 109.36 |
C6A—C5A—H9A | 109.20 | H19B—C15B—H20B | 109.44 |
C4A—C5A—H8A | 109.18 | C14B—C16B—H21B | 109.44 |
H10A—C6A—H11A | 107.97 | C14B—C16B—H22B | 109.49 |
C5A—C6A—H11A | 109.42 | C14B—C16B—H23B | 109.50 |
C1A—C6A—H10A | 109.35 | H21B—C16B—H22B | 109.51 |
C1A—C6A—H11A | 109.41 | H21B—C16B—H23B | 109.45 |
C5A—C6A—H10A | 109.33 | H22B—C16B—H23B | 109.44 |
C7A—C8A—H13A | 119.18 | C14B—C17B—H24B | 109.43 |
C9A—C8A—H13A | 119.16 | C14B—C17B—H25B | 109.44 |
C10A—C9A—H14A | 119.68 | C14B—C17B—H26B | 109.46 |
C8A—C9A—H14A | 119.79 | H24B—C17B—H25B | 109.48 |
C12A—C11A—H15A | 120.21 | H24B—C17B—H26B | 109.49 |
C10A—C11A—H15A | 120.23 | H25B—C17B—H26B | 109.52 |
| | | |
O3A—S1A—N3A—C13A | 55.56 (18) | C13B—N4B—C14B—C15B | 57.6 (3) |
O4A—S1A—N3A—C13A | −176.33 (16) | C13B—N4B—C14B—C16B | −64.1 (3) |
C12A—S1A—N3A—C13A | −60.45 (18) | C14B—N4B—C13B—N3B | 178.0 (2) |
N3A—S1A—C12A—C7A | −63.76 (19) | N1A—C1A—C2A—C3A | −174.8 (2) |
O3A—S1A—C12A—C11A | −3.9 (2) | C2A—C1A—C6A—C5A | 53.1 (3) |
O4A—S1A—C12A—C11A | −135.93 (17) | N1A—C1A—C6A—C5A | 175.5 (2) |
N3A—S1A—C12A—C11A | 112.41 (18) | C6A—C1A—C2A—C3A | −53.8 (3) |
O3A—S1A—C12A—C7A | 179.9 (2) | C1A—C2A—C3A—C4A | 55.0 (4) |
O4A—S1A—C12A—C7A | 47.9 (2) | C2A—C3A—C4A—C5A | −55.4 (4) |
O4B—S1B—N3B—C13B | −172.36 (16) | C3A—C4A—C5A—C6A | 55.9 (4) |
C12B—S1B—N3B—C13B | −57.54 (18) | C4A—C5A—C6A—C1A | −54.7 (3) |
O3B—S1B—C12B—C11B | −3.4 (2) | C12A—C7A—C8A—C9A | 3.6 (3) |
O4B—S1B—C12B—C11B | −135.12 (17) | C8A—C7A—C12A—S1A | 171.26 (16) |
N3B—S1B—C12B—C11B | 113.38 (17) | N1A—C7A—C12A—S1A | −8.5 (3) |
N3B—S1B—C12B—C7B | −62.8 (2) | C8A—C7A—C12A—C11A | −4.7 (3) |
O3B—S1B—N3B—C13B | 58.42 (19) | N1A—C7A—C12A—C11A | 175.5 (2) |
O4B—S1B—C12B—C7B | 48.7 (2) | N1A—C7A—C8A—C9A | −176.6 (2) |
O3B—S1B—C12B—C7B | −179.55 (17) | C7A—C8A—C9A—C10A | 0.0 (4) |
C1A—N1A—C7A—C12A | 167.5 (2) | C8A—C9A—C10A—N2A | 178.2 (2) |
C7A—N1A—C1A—C2A | −80.9 (3) | C8A—C9A—C10A—C11A | −2.8 (4) |
C7A—N1A—C1A—C6A | 156.4 (2) | C9A—C10A—C11A—C12A | 1.7 (4) |
C1A—N1A—C7A—C8A | −12.2 (3) | N2A—C10A—C11A—C12A | −179.3 (2) |
O1A—N2A—C10A—C11A | −168.7 (2) | C10A—C11A—C12A—S1A | −173.91 (18) |
O2A—N2A—C10A—C9A | −169.8 (3) | C10A—C11A—C12A—C7A | 2.2 (3) |
O1A—N2A—C10A—C9A | 10.3 (4) | C2B—C1B—C6B—C5B | 57.2 (3) |
O2A—N2A—C10A—C11A | 11.2 (4) | N1B—C1B—C6B—C5B | 179.0 (3) |
S1A—N3A—C13A—O5A | 0.8 (3) | C6B—C1B—C2B—C3B | −56.9 (4) |
S1A—N3A—C13A—N4A | 179.76 (14) | N1B—C1B—C2B—C3B | −178.3 (3) |
C14A—N4A—C13A—O5A | −6.8 (4) | C1B—C2B—C3B—C4B | 55.3 (4) |
C13A—N4A—C14A—C16A | −61.9 (3) | C2B—C3B—C4B—C5B | −54.1 (5) |
C13A—N4A—C14A—C15A | 60.7 (3) | C3B—C4B—C5B—C6B | 54.8 (5) |
C14A—N4A—C13A—N3A | 174.25 (18) | C4B—C5B—C6B—C1B | −56.0 (4) |
C13A—N4A—C14A—C17A | 179.9 (3) | N1B—C7B—C8B—C9B | −174.1 (2) |
C7B—N1B—C1B—C6B | 157.0 (2) | N1B—C7B—C12B—S1B | −8.8 (3) |
C7B—N1B—C1B—C2B | −81.0 (3) | C12B—C7B—C8B—C9B | 5.3 (3) |
C1B—N1B—C7B—C12B | 168.2 (2) | N1B—C7B—C12B—C11B | 175.2 (2) |
C1B—N1B—C7B—C8B | −12.4 (4) | C8B—C7B—C12B—S1B | 171.80 (17) |
O1B—N2B—C10B—C11B | −179.0 (2) | C8B—C7B—C12B—C11B | −4.2 (3) |
O2B—N2B—C10B—C9B | −179.5 (2) | C7B—C8B—C9B—C10B | −2.1 (4) |
O1B—N2B—C10B—C9B | −0.4 (4) | C8B—C9B—C10B—C11B | −2.5 (4) |
O2B—N2B—C10B—C11B | 2.0 (4) | C8B—C9B—C10B—N2B | 179.0 (2) |
S1B—N3B—C13B—O5B | −6.7 (3) | N2B—C10B—C11B—C12B | −177.9 (2) |
S1B—N3B—C13B—N4B | 172.15 (15) | C9B—C10B—C11B—C12B | 3.5 (3) |
C13B—N4B—C14B—C17B | 176.7 (2) | C10B—C11B—C12B—C7B | 0.0 (3) |
C14B—N4B—C13B—O5B | −3.3 (4) | C10B—C11B—C12B—S1B | −176.16 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H12A···O4A | 0.86 | 2.22 | 2.919 (3) | 139 |
N1B—H12B···O4B | 0.86 | 2.25 | 2.935 (3) | 137 |
N3A—H16A···O3B | 0.86 | 2.31 | 3.094 (3) | 153 |
N3B—H16B···O3Ai | 0.86 | 2.29 | 3.045 (3) | 147 |
N3B—H16B···O5Ai | 0.86 | 2.60 | 3.252 (3) | 134 |
N4A—H17A···O5B | 0.86 | 2.21 | 2.936 (3) | 142 |
N4B—H17B···O5Ai | 0.86 | 2.20 | 2.893 (3) | 137 |
C2B—H2B···O1Bii | 0.97 | 2.50 | 3.457 (4) | 168 |
C11A—H15A···O3A | 0.93 | 2.44 | 2.843 (3) | 107 |
C11B—H15B···O3B | 0.93 | 2.43 | 2.837 (3) | 107 |
C15A—H19A···O5A | 0.96 | 2.42 | 3.022 (4) | 121 |
C15B—H19B···O5B | 0.96 | 2.40 | 3.002 (5) | 120 |
C16A—H21A···O5A | 0.96 | 2.55 | 3.109 (3) | 117 |
C16B—H21B···O5B | 0.96 | 2.57 | 3.154 (4) | 119 |
C16A—H22A···O4Biii | 0.96 | 2.55 | 3.414 (3) | 150 |
C16B—H22B···O4Aiv | 0.96 | 2.59 | 3.399 (3) | 142 |
Symmetry codes: (i) −x+1/2, y−1/2, −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 formula | C17H26N4O5S |
Mr | 398.49 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 14.447 (5), 11.579 (5), 24.981 (5) |
β (°) | 95.195 (5) |
V (Å3) | 4162 (2) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 1.68 |
Crystal size (mm) | 0.42 × 0.17 × 0.13 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Analytical (de Meulenaer & Tompa, 1965) |
Tmin, Tmax | 0.539, 0.811 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11170, 8166, 5832 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.136, 1.04 |
No. of reflections | 8166 |
No. of parameters | 487 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.51 |
Selected torsion angles (º) topO1A—N2A—C10A—C11A | −168.7 (2) | O1B—N2B—C10B—C11B | −179.0 (2) |
O2A—N2A—C10A—C9A | −169.8 (3) | O2B—N2B—C10B—C9B | −179.5 (2) |
O1A—N2A—C10A—C9A | 10.3 (4) | O1B—N2B—C10B—C9B | −0.4 (4) |
O2A—N2A—C10A—C11A | 11.2 (4) | O2B—N2B—C10B—C11B | 2.0 (4) |
S1A—N3A—C13A—N4A | 179.76 (14) | S1B—N3B—C13B—N4B | 172.15 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H12A···O4A | 0.86 | 2.22 | 2.919 (3) | 139 |
N1B—H12B···O4B | 0.86 | 2.25 | 2.935 (3) | 137 |
N3A—H16A···O3B | 0.86 | 2.31 | 3.094 (3) | 153 |
N3B—H16B···O3Ai | 0.86 | 2.29 | 3.045 (3) | 147 |
N3B—H16B···O5Ai | 0.86 | 2.60 | 3.252 (3) | 134 |
N4A—H17A···O5B | 0.86 | 2.21 | 2.936 (3) | 142 |
N4B—H17B···O5Ai | 0.86 | 2.20 | 2.893 (3) | 137 |
C2B—H2B···O1Bii | 0.97 | 2.50 | 3.457 (4) | 168 |
C15A—H19A···O5A | 0.96 | 2.42 | 3.022 (4) | 121 |
C15B—H19B···O5B | 0.96 | 2.40 | 3.002 (5) | 120 |
C16A—H21A···O5A | 0.96 | 2.55 | 3.109 (3) | 117 |
C16B—H21B···O5B | 0.96 | 2.57 | 3.154 (4) | 119 |
C16A—H22A···O4Biii | 0.96 | 2.55 | 3.414 (3) | 150 |
C16B—H22B···O4Aiv | 0.96 | 2.59 | 3.399 (3) | 142 |
Symmetry codes: (i) −x+1/2, y−1/2, −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 topconformer | ϕ1 (1-2-3-4) | ϕ2 (2-3-4-5) | ϕ3 (3-4-5-6) | ϕ4 (4-5-6-7) |
α | -90 | 90 | 180 | 180 |
β | 90 | 90 | 180 | 0 |
γ | 90 | 90 | 180 | 180 |
δ | 90 | 90 | 0 | 180 |
ε | -90 | -90 | 180 | 180 |
Torsion angles (°) for the ε conformation of the
two asymmetric molecules of (I) top | ϕ1 | ϕ2 | ϕ3 | ϕ4 |
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) |
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).