Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009872/gs1099sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009872/gs1099Isup2.hkl |
CCDC reference: 152630
Terbogrel (0.173 g; supplier?) was dissolved in acetic acid (1 ml). This solution was then diluted with water (2 ml) and stored for 48 h at room temperature, after which time crystals of (I) formed?.
H atoms H5, H10, H24 and H30 were located in difference Fourier maps and then refined. All other H atoms were calculated geometrically and restrained to ride on their parent atoms, with Ueq(H) fixed to 1.2Ueq of the parent atoms.
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., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.
Fig. 1. ORTEP (Johnson, 1965) representation of (I) showing the hairpin-like conformation. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. |
C23H27N5O2 | F(000) = 864 |
Mr = 405.50 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 14.934 (1) Å | Cell parameters from 25 reflections |
b = 10.115 (1) Å | θ = 30–40° |
c = 15.740 (1) Å | µ = 0.65 mm−1 |
β = 113.049 (5)° | T = 293 K |
V = 2187.8 (3) Å3 | Polyhedral, colourless |
Z = 4 | 0.48 × 0.35 × 0.14 mm |
Enraf-Nonius CAD4 diffractometer | 3571 reflections with I > 2σ(I) |
Radiation source: long fine-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 71.9°, θmin = 3.2° |
θ/2θ scans | h = −18→15 |
Absorption correction: ψ scan (North et al., 1968) | k = −8→12 |
Tmin = 0.813, Tmax = 0.913 | l = 0→19 |
5986 measured reflections | 3 standard reflections every 200 reflections |
4252 independent reflections | intensity decay: 6% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.4729P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4252 reflections | Δρmax = 0.20 e Å−3 |
288 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0021 (2) |
C23H27N5O2 | V = 2187.8 (3) Å3 |
Mr = 405.50 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 14.934 (1) Å | µ = 0.65 mm−1 |
b = 10.115 (1) Å | T = 293 K |
c = 15.740 (1) Å | 0.48 × 0.35 × 0.14 mm |
β = 113.049 (5)° |
Enraf-Nonius CAD4 diffractometer | 3571 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.013 |
Tmin = 0.813, Tmax = 0.913 | 3 standard reflections every 200 reflections |
5986 measured reflections | intensity decay: 6% |
4252 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.20 e Å−3 |
4252 reflections | Δρmin = −0.18 e Å−3 |
288 parameters |
Experimental. Tmin and Tmax were generated by HELENA (psi-scan correction) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.08328 (15) | 0.0187 (2) | 0.88663 (13) | 0.0763 (6) | |
H1A | 1.0424 | −0.0566 | 0.8819 | 0.114* | |
H1B | 1.1264 | 0.0312 | 0.9499 | 0.114* | |
H1C | 1.1207 | 0.0042 | 0.8499 | 0.114* | |
C2 | 1.08166 (13) | 0.26184 (19) | 0.85382 (13) | 0.0662 (5) | |
H2A | 1.1160 | 0.2471 | 0.8144 | 0.099* | |
H2B | 1.1275 | 0.2773 | 0.9158 | 0.099* | |
H2C | 1.0400 | 0.3375 | 0.8324 | 0.099* | |
C3 | 0.96335 (13) | 0.1680 (2) | 0.91192 (11) | 0.0662 (5) | |
H3A | 0.9213 | 0.2426 | 0.8877 | 0.099* | |
H3B | 1.0077 | 0.1866 | 0.9740 | 0.099* | |
H3C | 0.9249 | 0.0918 | 0.9118 | 0.099* | |
C4 | 1.02051 (10) | 0.14085 (15) | 0.85219 (9) | 0.0442 (3) | |
N5 | 0.94693 (8) | 0.12065 (12) | 0.75740 (7) | 0.0399 (3) | |
H5 | 0.8880 (12) | 0.1047 (15) | 0.7519 (11) | 0.049 (4)* | |
C6 | 0.96475 (9) | 0.10485 (13) | 0.68113 (9) | 0.0366 (3) | |
N7 | 1.05604 (8) | 0.09022 (13) | 0.69011 (8) | 0.0465 (3) | |
C8 | 1.07929 (9) | 0.07551 (16) | 0.61872 (10) | 0.0458 (3) | |
N9 | 1.11025 (10) | 0.05886 (18) | 0.56317 (10) | 0.0680 (4) | |
N10 | 0.88886 (8) | 0.10299 (12) | 0.59729 (8) | 0.0405 (3) | |
H10 | 0.9001 (11) | 0.0617 (16) | 0.5535 (12) | 0.053 (4)* | |
C11 | 0.78889 (9) | 0.12373 (12) | 0.57780 (8) | 0.0336 (3) | |
C12 | 0.72172 (9) | 0.04607 (13) | 0.50961 (9) | 0.0388 (3) | |
H12 | 0.7430 | −0.0177 | 0.4792 | 0.047* | |
C13 | 0.62338 (10) | 0.06382 (14) | 0.48710 (9) | 0.0431 (3) | |
H13 | 0.5786 | 0.0133 | 0.4403 | 0.052* | |
C14 | 0.59069 (9) | 0.15601 (14) | 0.53340 (9) | 0.0394 (3) | |
H14 | 0.5244 | 0.1653 | 0.5189 | 0.047* | |
C15 | 0.65697 (9) | 0.23481 (12) | 0.60165 (8) | 0.0333 (3) | |
C16 | 0.75602 (9) | 0.22091 (12) | 0.62122 (8) | 0.0348 (3) | |
H16 | 0.8005 | 0.2772 | 0.6637 | 0.042* | |
C17 | 0.62346 (9) | 0.33251 (12) | 0.65423 (9) | 0.0356 (3) | |
C18 | 0.64529 (9) | 0.47432 (12) | 0.64555 (9) | 0.0358 (3) | |
C19 | 0.63575 (10) | 0.52835 (14) | 0.56121 (10) | 0.0451 (3) | |
H19 | 0.6190 | 0.4746 | 0.5093 | 0.054* | |
C20 | 0.65116 (12) | 0.66165 (15) | 0.55459 (11) | 0.0528 (4) | |
H20 | 0.6456 | 0.6986 | 0.4986 | 0.063* | |
C21 | 0.67480 (11) | 0.73887 (15) | 0.63193 (11) | 0.0515 (4) | |
H21 | 0.6837 | 0.8291 | 0.6269 | 0.062* | |
N22 | 0.68555 (9) | 0.68985 (12) | 0.71417 (9) | 0.0483 (3) | |
C23 | 0.67238 (10) | 0.56039 (13) | 0.72015 (10) | 0.0419 (3) | |
H23 | 0.6819 | 0.5256 | 0.7777 | 0.050* | |
C24 | 0.57394 (10) | 0.29827 (14) | 0.70536 (10) | 0.0413 (3) | |
H24 | 0.5541 (11) | 0.3688 (15) | 0.7359 (11) | 0.048 (4)* | |
C25 | 0.54620 (10) | 0.16305 (14) | 0.72486 (10) | 0.0432 (3) | |
H25A | 0.5679 | 0.0983 | 0.6916 | 0.052* | |
H25B | 0.4759 | 0.1572 | 0.7025 | 0.052* | |
C26 | 0.59052 (11) | 0.13039 (14) | 0.82789 (10) | 0.0456 (3) | |
H26A | 0.5778 | 0.2027 | 0.8621 | 0.055* | |
H26B | 0.5593 | 0.0519 | 0.8389 | 0.055* | |
C27 | 0.70013 (11) | 0.10697 (14) | 0.86361 (10) | 0.0489 (3) | |
H27A | 0.7313 | 0.1847 | 0.8515 | 0.059* | |
H27B | 0.7256 | 0.0936 | 0.9299 | 0.059* | |
C28 | 0.72410 (10) | −0.01093 (14) | 0.81872 (10) | 0.0460 (3) | |
O29 | 0.76994 (9) | −0.00641 (12) | 0.77071 (9) | 0.0641 (3) | |
O30 | 0.68680 (10) | −0.12204 (11) | 0.83429 (10) | 0.0681 (4) | |
H30 | 0.698 (2) | −0.196 (3) | 0.7966 (19) | 0.127 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0775 (12) | 0.0887 (14) | 0.0561 (10) | 0.0253 (11) | 0.0191 (9) | 0.0199 (10) |
C2 | 0.0621 (10) | 0.0753 (12) | 0.0648 (11) | −0.0232 (9) | 0.0286 (9) | −0.0221 (9) |
C3 | 0.0587 (9) | 0.1049 (14) | 0.0416 (8) | −0.0106 (10) | 0.0268 (7) | −0.0181 (9) |
C4 | 0.0399 (7) | 0.0580 (8) | 0.0352 (7) | −0.0012 (6) | 0.0152 (6) | −0.0050 (6) |
N5 | 0.0321 (6) | 0.0566 (7) | 0.0349 (6) | −0.0010 (5) | 0.0172 (5) | −0.0047 (5) |
C6 | 0.0343 (6) | 0.0419 (7) | 0.0372 (6) | 0.0017 (5) | 0.0178 (5) | −0.0030 (5) |
N7 | 0.0339 (6) | 0.0701 (8) | 0.0398 (6) | 0.0033 (5) | 0.0191 (5) | −0.0058 (6) |
C8 | 0.0324 (6) | 0.0650 (9) | 0.0422 (7) | 0.0033 (6) | 0.0169 (6) | −0.0052 (7) |
N9 | 0.0510 (8) | 0.1096 (12) | 0.0530 (8) | 0.0066 (8) | 0.0306 (7) | −0.0127 (8) |
N10 | 0.0340 (6) | 0.0563 (7) | 0.0350 (6) | 0.0059 (5) | 0.0177 (5) | −0.0075 (5) |
C11 | 0.0330 (6) | 0.0386 (6) | 0.0326 (6) | 0.0019 (5) | 0.0166 (5) | 0.0008 (5) |
C12 | 0.0426 (7) | 0.0412 (7) | 0.0361 (6) | 0.0011 (6) | 0.0191 (6) | −0.0055 (5) |
C13 | 0.0403 (7) | 0.0498 (8) | 0.0373 (7) | −0.0068 (6) | 0.0132 (6) | −0.0096 (6) |
C14 | 0.0316 (6) | 0.0477 (7) | 0.0392 (7) | 0.0000 (5) | 0.0142 (5) | −0.0013 (6) |
C15 | 0.0343 (6) | 0.0339 (6) | 0.0344 (6) | 0.0030 (5) | 0.0164 (5) | 0.0020 (5) |
C16 | 0.0326 (6) | 0.0356 (6) | 0.0373 (6) | −0.0012 (5) | 0.0151 (5) | −0.0043 (5) |
C17 | 0.0321 (6) | 0.0374 (7) | 0.0380 (6) | 0.0052 (5) | 0.0146 (5) | −0.0008 (5) |
C18 | 0.0315 (6) | 0.0380 (7) | 0.0409 (7) | 0.0073 (5) | 0.0174 (5) | 0.0016 (5) |
C19 | 0.0470 (7) | 0.0495 (8) | 0.0413 (7) | 0.0059 (6) | 0.0201 (6) | 0.0009 (6) |
C20 | 0.0595 (9) | 0.0515 (9) | 0.0512 (8) | 0.0077 (7) | 0.0257 (7) | 0.0146 (7) |
C21 | 0.0540 (9) | 0.0393 (7) | 0.0650 (10) | 0.0048 (6) | 0.0274 (8) | 0.0079 (7) |
N22 | 0.0529 (7) | 0.0399 (6) | 0.0564 (7) | 0.0013 (5) | 0.0261 (6) | −0.0024 (5) |
C23 | 0.0460 (7) | 0.0399 (7) | 0.0435 (7) | 0.0026 (6) | 0.0215 (6) | 0.0001 (6) |
C24 | 0.0409 (7) | 0.0419 (7) | 0.0474 (7) | 0.0038 (6) | 0.0243 (6) | −0.0034 (6) |
C25 | 0.0416 (7) | 0.0468 (7) | 0.0473 (7) | −0.0057 (6) | 0.0240 (6) | −0.0060 (6) |
C26 | 0.0568 (8) | 0.0439 (7) | 0.0466 (8) | −0.0082 (6) | 0.0317 (7) | −0.0079 (6) |
C27 | 0.0547 (8) | 0.0460 (8) | 0.0451 (8) | −0.0106 (6) | 0.0185 (7) | −0.0065 (6) |
C28 | 0.0457 (7) | 0.0458 (8) | 0.0479 (8) | −0.0062 (6) | 0.0199 (6) | 0.0004 (6) |
O29 | 0.0725 (7) | 0.0606 (7) | 0.0773 (8) | −0.0160 (6) | 0.0490 (7) | −0.0096 (6) |
O30 | 0.0995 (10) | 0.0443 (6) | 0.0866 (9) | −0.0130 (6) | 0.0646 (8) | −0.0072 (6) |
N10—C6 | 1.3621 (17) | O29—C28 | 1.2028 (17) |
N10—C11 | 1.4173 (16) | O30—C28 | 1.3192 (17) |
N10—H10 | 0.877 (17) | O30—H30 | 1.01 (3) |
C18—C23 | 1.3887 (18) | C12—H12 | 0.9300 |
C18—C19 | 1.3903 (18) | C19—C20 | 1.379 (2) |
C18—C17 | 1.4892 (18) | C19—H19 | 0.9300 |
C15—C14 | 1.3916 (18) | N22—C21 | 1.3359 (19) |
C15—C16 | 1.3950 (17) | C26—C27 | 1.527 (2) |
C15—C17 | 1.4954 (16) | C26—C25 | 1.529 (2) |
C24—C17 | 1.3344 (18) | C26—H26A | 0.9700 |
C24—C25 | 1.4954 (19) | C26—H26B | 0.9700 |
C24—H24 | 0.969 (16) | N9—C8 | 1.1504 (18) |
C16—C11 | 1.3916 (16) | C25—H25A | 0.9700 |
C16—H16 | 0.9300 | C25—H25B | 0.9700 |
C11—C12 | 1.3901 (18) | C28—C27 | 1.499 (2) |
C6—N7 | 1.3226 (16) | C21—C20 | 1.371 (2) |
C6—N5 | 1.3371 (16) | C21—H21 | 0.9300 |
N5—C4 | 1.4804 (17) | C27—H27A | 0.9700 |
N5—H5 | 0.865 (17) | C27—H27B | 0.9700 |
C4—C1 | 1.517 (2) | C20—H20 | 0.9300 |
C4—C2 | 1.521 (2) | C2—H2A | 0.9600 |
C4—C3 | 1.5219 (19) | C2—H2B | 0.9600 |
N7—C8 | 1.3080 (17) | C2—H2C | 0.9600 |
C14—C13 | 1.3848 (19) | C3—H3A | 0.9600 |
C14—H14 | 0.9300 | C3—H3B | 0.9600 |
C13—C12 | 1.3810 (19) | C3—H3C | 0.9600 |
C13—H13 | 0.9300 | C1—H1A | 0.9600 |
C23—N22 | 1.3330 (18) | C1—H1B | 0.9600 |
C23—H23 | 0.9300 | C1—H1C | 0.9600 |
C6—N10—C11 | 127.88 (11) | C18—C19—H19 | 120.0 |
C6—N10—H10 | 115.2 (11) | C23—N22—C21 | 117.90 (13) |
C11—N10—H10 | 114.3 (10) | C27—C26—C25 | 112.38 (11) |
C23—C18—C19 | 116.61 (12) | C27—C26—H26A | 109.1 |
C23—C18—C17 | 121.88 (11) | C25—C26—H26A | 109.1 |
C19—C18—C17 | 121.46 (12) | C27—C26—H26B | 109.1 |
C14—C15—C16 | 119.01 (11) | C25—C26—H26B | 109.1 |
C14—C15—C17 | 120.97 (11) | H26A—C26—H26B | 107.9 |
C16—C15—C17 | 120.01 (11) | N9—C8—N7 | 172.12 (15) |
C17—C24—C25 | 128.66 (12) | C24—C25—C26 | 112.07 (12) |
C17—C24—H24 | 117.2 (9) | C24—C25—H25A | 109.2 |
C25—C24—H24 | 114.1 (9) | C26—C25—H25A | 109.2 |
C24—C17—C18 | 119.89 (11) | C24—C25—H25B | 109.2 |
C24—C17—C15 | 123.15 (12) | C26—C25—H25B | 109.2 |
C18—C17—C15 | 116.94 (10) | H25A—C25—H25B | 107.9 |
C11—C16—C15 | 120.67 (11) | O29—C28—O30 | 122.32 (14) |
C11—C16—H16 | 119.7 | O29—C28—C27 | 124.44 (13) |
C15—C16—H16 | 119.7 | O30—C28—C27 | 113.20 (12) |
C12—C11—C16 | 119.46 (11) | N22—C21—C20 | 122.71 (14) |
C12—C11—N10 | 117.64 (11) | N22—C21—H21 | 118.6 |
C16—C11—N10 | 122.85 (11) | C20—C21—H21 | 118.6 |
N7—C6—N5 | 118.46 (12) | C28—C27—C26 | 111.67 (12) |
N7—C6—N10 | 122.26 (11) | C28—C27—H27A | 109.3 |
N5—C6—N10 | 119.28 (11) | C26—C27—H27A | 109.3 |
C6—N5—C4 | 126.25 (11) | C28—C27—H27B | 109.3 |
C6—N5—H5 | 116.1 (11) | C26—C27—H27B | 109.3 |
C4—N5—H5 | 116.9 (11) | H27A—C27—H27B | 107.9 |
N5—C4—C1 | 111.01 (13) | C21—C20—C19 | 118.85 (14) |
N5—C4—C2 | 109.39 (12) | C21—C20—H20 | 120.6 |
C1—C4—C2 | 111.49 (14) | C19—C20—H20 | 120.6 |
N5—C4—C3 | 105.83 (11) | C4—C2—H2A | 109.5 |
C1—C4—C3 | 110.10 (14) | C4—C2—H2B | 109.5 |
C2—C4—C3 | 108.84 (13) | H2A—C2—H2B | 109.5 |
C8—N7—C6 | 122.01 (12) | C4—C2—H2C | 109.5 |
C13—C14—C15 | 120.08 (12) | H2A—C2—H2C | 109.5 |
C13—C14—H14 | 120.0 | H2B—C2—H2C | 109.5 |
C15—C14—H14 | 120.0 | C4—C3—H3A | 109.5 |
C12—C13—C14 | 120.74 (12) | C4—C3—H3B | 109.5 |
C12—C13—H13 | 119.6 | H3A—C3—H3B | 109.5 |
C14—C13—H13 | 119.6 | C4—C3—H3C | 109.5 |
N22—C23—C18 | 123.94 (13) | H3A—C3—H3C | 109.5 |
N22—C23—H23 | 118.0 | H3B—C3—H3C | 109.5 |
C18—C23—H23 | 118.0 | C4—C1—H1A | 109.5 |
C28—O30—H30 | 109.9 (15) | C4—C1—H1B | 109.5 |
C13—C12—C11 | 119.87 (11) | H1A—C1—H1B | 109.5 |
C13—C12—H12 | 120.1 | C4—C1—H1C | 109.5 |
C11—C12—H12 | 120.1 | H1A—C1—H1C | 109.5 |
C20—C19—C18 | 119.93 (14) | H1B—C1—H1C | 109.5 |
C20—C19—H19 | 120.0 | ||
C25—C24—C17—C18 | −178.61 (13) | N5—C6—N7—C8 | −179.36 (14) |
C25—C24—C17—C15 | 3.1 (2) | N10—C6—N7—C8 | 1.3 (2) |
C23—C18—C17—C24 | 40.04 (18) | C16—C15—C14—C13 | 1.13 (19) |
C19—C18—C17—C24 | −137.36 (14) | C17—C15—C14—C13 | −178.39 (12) |
C23—C18—C17—C15 | −141.58 (12) | C15—C14—C13—C12 | 1.9 (2) |
C19—C18—C17—C15 | 41.02 (17) | C19—C18—C23—N22 | 2.7 (2) |
C14—C15—C17—C24 | 59.98 (18) | C17—C18—C23—N22 | −174.80 (12) |
C16—C15—C17—C24 | −119.53 (14) | C14—C13—C12—C11 | −1.7 (2) |
C14—C15—C17—C18 | −118.34 (13) | C16—C11—C12—C13 | −1.50 (19) |
C16—C15—C17—C18 | 62.15 (16) | N10—C11—C12—C13 | −179.04 (12) |
C14—C15—C16—C11 | −4.34 (18) | C23—C18—C19—C20 | −1.25 (19) |
C17—C15—C16—C11 | 175.18 (11) | C17—C18—C19—C20 | 176.27 (12) |
C15—C16—C11—C12 | 4.54 (19) | C18—C23—N22—C21 | −2.1 (2) |
C15—C16—C11—N10 | −178.06 (11) | C6—N7—C8—N9 | −169.1 (13) |
C6—N10—C11—C12 | −141.37 (14) | C17—C24—C25—C26 | 118.85 (16) |
C6—N10—C11—C16 | 41.2 (2) | C27—C26—C25—C24 | −71.72 (15) |
C11—N10—C6—N7 | −176.67 (13) | C23—N22—C21—C20 | −0.1 (2) |
C11—N10—C6—N5 | 4.0 (2) | O29—C28—C27—C26 | 116.81 (17) |
N7—C6—N5—C4 | 8.4 (2) | O30—C28—C27—C26 | −60.95 (17) |
N10—C6—N5—C4 | −172.22 (13) | C25—C26—C27—C28 | −63.41 (16) |
C6—N5—C4—C1 | −66.44 (18) | N22—C21—C20—C19 | 1.4 (2) |
C6—N5—C4—C2 | 57.01 (18) | C18—C19—C20—C21 | −0.7 (2) |
C6—N5—C4—C3 | 174.12 (14) |
D—H···A | H···A | D···A | D—H···A |
N5—H5···O29 | 2.206 (18) | 3.019 (2) | 156.4 (14) |
N10—H10···N9i | 2.159 (17) | 3.014 (2) | 165.0 (16) |
O30—H30···N22ii | 1.69 (3) | 2.677 (2) | 164 (3) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C23H27N5O2 |
Mr | 405.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.934 (1), 10.115 (1), 15.740 (1) |
β (°) | 113.049 (5) |
V (Å3) | 2187.8 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.48 × 0.35 × 0.14 |
Data collection | |
Diffractometer | Enraf-Nonius CAD4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.813, 0.913 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5986, 4252, 3571 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.105, 1.05 |
No. of reflections | 4252 |
No. of parameters | 288 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.18 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, HELENA (Spek, 1997), SIR97 (Altomare et al., 1998), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990), SHELXL97.
D—H···A | H···A | D···A | D—H···A |
N5—H5···O29 | 2.206 (18) | 3.019 (2) | 156.4 (14) |
N10—H10···N9i | 2.159 (17) | 3.014 (2) | 165.0 (16) |
O30—H30···N22ii | 1.69 (3) | 2.677 (2) | 164 (3) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y−1, z. |
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Terbogrel, (I), is a combined thromboxane A2 receptor antagonist (TRA) and thromboxane A2 synthase inhibitor (TxSI) (Soyka et al., 1999). In order to understand this dual mode of action, the structural properties of the compound have been studied and the results are presented here. \sch
A folded hairpin-like conformer is observed (Fig. 1), confirming the assumption of Andersen et al. (1976) that TXA2 receptor binding requires a prostaglandin conformation, with a U-shaped or approximately parallel arrangement of the α and ω side chains (the so-called hairpin conformation hypothesis). Such a conformation was also observed in S-145, a potent TRA, by Ezumi et al. (1990).
The crystal packing of (I) was then analysed and mainly intra- and intermolecular hydrogen bonds observed (Table 1). The hairpin-like conformation is stabilized by an intramolecular hydrogen bond between N5—H5 and the terminal carboxyl (O29) of the molecule (Fig. 1), as predicted by Takasuka et al. (1991). Intermolecular hydrogen bonds are found between atom N9 of the cyanoguanidine group and N10—H10. Thus `clippers' seem to be formed between the molecules. Another intermolecular bond is observed between atom N22 of the pyridine and the carboxyl function. All these groups are thought to be potential anchoring sites for the TXA2 receptor.
In the case of TxSIs, the essential structural features for activity are a basic N atom (a 3-substituted pyridine here) and a carboxylic acid group separated by a distance of 8–10 Å (Iizuka et al., 1981). In (I), a distance of 8.4257 (19) Å is observed between N22 and O30.
In conclusion, two structural features of terbogrel can support its dual action: its hairpin-like conformation for the TRA mode and the two groups separated by 8.4257 (19) Å for the TxSI mode.