The novel crystal structures of ethyl (S)-P-(4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)-N-[(R)-1-phenylethyl]phosphonamidate, C20H20N3O3PS, I, and diethyl (4-isopropyl-2-oxo-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)phosphonate, C18H25N2O4PS, II, were characterized by X-ray diffraction analysis. The crystal packing of I is dominated by two infinite stacks composed of symmetry-independent molecules linked by distinctively different hydrogen-bond systems. The structure of II shows a ladder packing topology similar to those observed in related phosphorylated azaheterocycles. Structural studies are supplemented by calculations on the interactions stabilizing the molecular assemblies using the PIXEL method. Additionally, fingerprint plots derived from the Hirshfeld surfaces were generated for each structure to characterize the crystal packing arrangements in detail. The aromaticities of the heterocyclic moieties have been investigated using HOMA and HOMHED parametrization and compared with structures reported previously.
Supporting information
CCDC references: 1853462; 1853461
Data collection: APEX2 (Bruker, 2014) for (I); CrysAlis PRO (Rigaku OD, 2017) for (II). Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for (I); CrysAlis PRO (Rigaku OD, 2017) for (II). Data reduction: CrysAlis PRO (Rigaku OD, 2018) for (I); CrysAlis PRO (Rigaku OD, 2017) for (II). For both structures, program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: Mercury (Macrae et al., 2008) for (I). Software used to prepare material for publication: publCIF (Westrip, 2010) for (I); SHELXL2018 (Sheldrick, 2015b) for (II).
Ethyl (
S)-
P-(4-oxo-4
H-benzo[4,5]thiazolo[3,2-
a]pyrimidin-3-yl)-
N-[(
R)-1-phenylethyl]phosphonamidate (I)
top
Crystal data top
C20H20N3O3PS | F(000) = 864 |
Mr = 413.42 | Dx = 1.427 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 16.4417 (7) Å | Cell parameters from 11973 reflections |
b = 5.1623 (2) Å | θ = 2.9–70.3° |
c = 23.7712 (9) Å | µ = 2.51 mm−1 |
β = 107.430 (4)° | T = 100 K |
V = 1924.99 (14) Å3 | Needle, colourless |
Z = 4 | 0.1 × 0.07 × 0.03 mm |
Data collection top
Bruker SMART APEXII diffractometer | 6183 reflections with I > 2σ(I) |
Radiation source: sealed X-ray microsource | Rint = 0.045 |
ω scans | θmax = 67.1°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | h = −19→19 |
Tmin = 0.460, Tmax = 1.000 | k = −6→6 |
20421 measured reflections | l = −28→27 |
6723 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[σ2(Fo2) + (0.1069P)2 + 0.7717P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.43 e Å−3 |
6723 reflections | Δρmin = −0.40 e Å−3 |
554 parameters | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. |
194 restraints | Absolute structure parameter: −0.01 (3) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1A | 0.44382 (8) | −0.1508 (2) | 0.12851 (6) | 0.0281 (3) | |
P1B | 0.14833 (8) | 0.7025 (3) | 0.43466 (6) | 0.0299 (3) | |
S1A | 0.83195 (8) | 0.0044 (3) | 0.16721 (6) | 0.0385 (3) | |
S1B | 0.38153 (9) | 0.4374 (3) | 0.68539 (6) | 0.0382 (3) | |
O1A | 0.5962 (2) | −0.4448 (7) | 0.21073 (15) | 0.0307 (8) | |
O2A | 0.4312 (2) | −0.0789 (7) | 0.19040 (16) | 0.0322 (8) | |
O4B | 0.1202 (2) | 0.4504 (7) | 0.40532 (16) | 0.0346 (8) | |
O2B | 0.0808 (2) | 0.8659 (8) | 0.45502 (15) | 0.0338 (8) | |
O1B | 0.3121 (3) | 0.3723 (8) | 0.47081 (16) | 0.0407 (9) | |
O4A | 0.4198 (2) | −0.4181 (7) | 0.10780 (18) | 0.0361 (9) | |
N2A | 0.7019 (3) | −0.2062 (8) | 0.18928 (18) | 0.0282 (9) | |
N3A | 0.3895 (3) | 0.0603 (9) | 0.08194 (19) | 0.0305 (9) | |
H3A | 0.400 (3) | 0.227 (13) | 0.092 (2) | 0.024 (13)* | |
N2B | 0.3385 (3) | 0.4177 (9) | 0.57113 (18) | 0.0313 (9) | |
N3B | 0.1813 (3) | 0.8973 (9) | 0.39288 (19) | 0.0326 (10) | |
H3B | 0.189 (5) | 1.065 (19) | 0.401 (3) | 0.06 (2)* | |
NA | 0.6693 (3) | 0.1535 (9) | 0.1229 (2) | 0.0338 (10) | |
N1B | 0.2658 (3) | 0.7365 (10) | 0.6118 (2) | 0.0381 (11) | |
C10A | 0.6144 (3) | −0.2642 (11) | 0.1832 (2) | 0.0295 (10) | |
C34A | 0.2243 (8) | 0.304 (3) | 0.0207 (7) | 0.046 (3) | 0.544 (18) |
H34A | 0.265022 | 0.422217 | 0.041385 | 0.055* | 0.544 (18) |
C35A | 0.1378 (8) | 0.369 (4) | 0.0064 (7) | 0.058 (4) | 0.544 (18) |
H35A | 0.119572 | 0.526504 | 0.017169 | 0.070* | 0.544 (18) |
C37A | 0.1035 (9) | −0.054 (4) | −0.0394 (9) | 0.067 (5) | 0.544 (18) |
H37A | 0.064599 | −0.180527 | −0.058389 | 0.080* | 0.544 (18) |
C38A | 0.1902 (8) | −0.108 (3) | −0.0246 (8) | 0.055 (4) | 0.544 (18) |
H38A | 0.207334 | −0.268702 | −0.034818 | 0.066* | 0.544 (18) |
C31A | 0.3456 (3) | 0.0046 (10) | 0.0194 (2) | 0.0314 (11) | |
H31A | 0.351942 | −0.180884 | 0.012930 | 0.038* | |
C1A | 0.5561 (3) | −0.0909 (10) | 0.1441 (2) | 0.0276 (10) | |
C10B | 0.2927 (3) | 0.4749 (11) | 0.5112 (2) | 0.0322 (11) | |
C9A | 0.7735 (3) | −0.3405 (10) | 0.2259 (2) | 0.0301 (11) | |
C3A | 0.7229 (3) | −0.0085 (10) | 0.1574 (2) | 0.0327 (11) | |
C5A | 0.9286 (3) | −0.3446 (11) | 0.2516 (2) | 0.0353 (12) | |
H5A | 0.979111 | −0.282752 | 0.246682 | 0.042* | |
C21B | 0.0007 (3) | 0.9464 (11) | 0.4135 (2) | 0.0360 (12) | |
H21C | 0.001251 | 0.911311 | 0.373483 | 0.043* | |
H21D | −0.007395 | 1.131011 | 0.417178 | 0.043* | |
C33B | 0.1688 (3) | 0.8696 (10) | 0.2863 (2) | 0.0305 (11) | |
C9B | 0.4019 (3) | 0.2264 (11) | 0.5904 (2) | 0.0336 (11) | |
C8B | 0.4346 (4) | 0.0596 (12) | 0.5562 (3) | 0.0384 (13) | |
H8B | 0.415717 | 0.069019 | 0.515218 | 0.046* | |
C7B | 0.4953 (4) | −0.1191 (13) | 0.5844 (3) | 0.0447 (14) | |
H7B | 0.518045 | −0.230201 | 0.562282 | 0.054* | |
C2A | 0.5864 (3) | 0.1096 (11) | 0.1179 (2) | 0.0324 (11) | |
H2A | 0.546597 | 0.224226 | 0.094801 | 0.039* | |
C38B | 0.1737 (4) | 0.7088 (12) | 0.2405 (2) | 0.0360 (12) | |
H38B | 0.209280 | 0.564893 | 0.249048 | 0.043* | |
C32A | 0.3866 (4) | 0.1530 (11) | −0.0207 (2) | 0.0371 (12) | |
H32A | 0.356093 | 0.117443 | −0.061165 | 0.056* | |
H32B | 0.444871 | 0.099547 | −0.012741 | 0.056* | |
H32C | 0.384560 | 0.335450 | −0.013376 | 0.056* | |
C6A | 0.9290 (3) | −0.5385 (12) | 0.2924 (2) | 0.0370 (12) | |
H6A | 0.980684 | −0.607020 | 0.315167 | 0.044* | |
C2B | 0.2168 (4) | 0.7849 (11) | 0.5555 (2) | 0.0344 (12) | |
H2B | 0.174948 | 0.911643 | 0.550031 | 0.041* | |
C5B | 0.4917 (4) | 0.0313 (13) | 0.6805 (3) | 0.0402 (13) | |
H5B | 0.511057 | 0.022578 | 0.721437 | 0.048* | |
C1B | 0.2246 (3) | 0.6602 (10) | 0.5062 (2) | 0.0321 (11) | |
C4A | 0.8495 (3) | −0.2457 (11) | 0.2183 (2) | 0.0333 (11) | |
C31B | 0.2222 (3) | 0.8089 (11) | 0.3492 (2) | 0.0310 (11) | |
H31B | 0.227859 | 0.620117 | 0.352713 | 0.037* | |
C8A | 0.7744 (3) | −0.5344 (11) | 0.2668 (2) | 0.0331 (11) | |
H8A | 0.724159 | −0.596657 | 0.272152 | 0.040* | |
C34B | 0.1155 (4) | 1.0857 (11) | 0.2725 (2) | 0.0354 (12) | |
H34B | 0.111368 | 1.196882 | 0.302269 | 0.043* | |
C4B | 0.4312 (3) | 0.2103 (11) | 0.6525 (2) | 0.0344 (11) | |
C22B | −0.0704 (4) | 0.7994 (12) | 0.4263 (3) | 0.0422 (13) | |
H22D | −0.123471 | 0.843290 | 0.397591 | 0.063* | |
H22E | −0.072959 | 0.844050 | 0.464960 | 0.063* | |
H22F | −0.060355 | 0.616786 | 0.424628 | 0.063* | |
C7A | 0.8534 (4) | −0.6311 (12) | 0.2994 (3) | 0.0392 (13) | |
H7A | 0.855656 | −0.761767 | 0.326776 | 0.047* | |
C35B | 0.0686 (4) | 1.1353 (12) | 0.2144 (3) | 0.0388 (12) | |
H35B | 0.033493 | 1.280259 | 0.205581 | 0.047* | |
C21A | 0.3449 (4) | −0.0840 (11) | 0.1948 (3) | 0.0371 (12) | |
H21A | 0.343394 | −0.188111 | 0.228452 | 0.045* | |
H21B | 0.306883 | −0.162334 | 0.159610 | 0.045* | |
C22A | 0.3151 (4) | 0.1883 (12) | 0.2018 (3) | 0.0395 (13) | |
H22A | 0.257809 | 0.182695 | 0.204072 | 0.059* | |
H22B | 0.316682 | 0.291077 | 0.168459 | 0.059* | |
H22C | 0.351874 | 0.263802 | 0.237189 | 0.059* | |
C3B | 0.3211 (4) | 0.5505 (11) | 0.6170 (2) | 0.0349 (12) | |
C32B | 0.3119 (3) | 0.9220 (14) | 0.3623 (3) | 0.0425 (13) | |
H32D | 0.337800 | 0.859328 | 0.333678 | 0.064* | |
H32E | 0.345608 | 0.870061 | 0.401001 | 0.064* | |
H32F | 0.308510 | 1.107574 | 0.360309 | 0.064* | |
C37B | 0.1267 (4) | 0.7574 (13) | 0.1824 (3) | 0.0432 (14) | |
H37B | 0.130777 | 0.647343 | 0.152366 | 0.052* | |
C36B | 0.0736 (4) | 0.9725 (13) | 0.1697 (3) | 0.0436 (14) | |
H36B | 0.041484 | 1.006508 | 0.130976 | 0.052* | |
C6B | 0.5234 (4) | −0.1360 (13) | 0.6464 (3) | 0.0445 (14) | |
H6B | 0.563476 | −0.260463 | 0.664639 | 0.053* | |
C33A | 0.2507 (3) | 0.0631 (11) | 0.0041 (2) | 0.0351 (11) | |
C34D | 0.2113 (10) | 0.180 (5) | 0.0400 (7) | 0.052 (4) | 0.456 (18) |
H34D | 0.244254 | 0.235478 | 0.077098 | 0.063* | 0.456 (18) |
C35D | 0.1238 (10) | 0.221 (4) | 0.0238 (7) | 0.052 (4) | 0.456 (18) |
H35D | 0.099702 | 0.291365 | 0.051179 | 0.063* | 0.456 (18) |
C36A | 0.0758 (4) | 0.1659 (18) | −0.0275 (3) | 0.0617 (19) | |
H36A | 0.017579 | 0.200476 | −0.039793 | 0.074* | |
C37D | 0.1111 (10) | 0.043 (3) | −0.0701 (9) | 0.050 (4) | 0.456 (18) |
H37D | 0.076739 | −0.000039 | −0.107722 | 0.060* | 0.456 (18) |
C38D | 0.1985 (9) | −0.008 (3) | −0.0525 (8) | 0.047 (4) | 0.456 (18) |
H38D | 0.222602 | −0.090570 | −0.078405 | 0.056* | 0.456 (18) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1A | 0.0325 (6) | 0.0188 (6) | 0.0293 (6) | −0.0004 (5) | 0.0038 (5) | −0.0002 (5) |
P1B | 0.0356 (6) | 0.0230 (6) | 0.0282 (6) | −0.0003 (5) | 0.0051 (5) | 0.0018 (5) |
S1A | 0.0345 (6) | 0.0355 (7) | 0.0418 (7) | −0.0020 (5) | 0.0056 (5) | 0.0100 (6) |
S1B | 0.0467 (7) | 0.0362 (7) | 0.0281 (6) | 0.0104 (6) | 0.0058 (5) | 0.0011 (6) |
O1A | 0.0352 (18) | 0.0245 (18) | 0.0297 (18) | −0.0012 (14) | 0.0054 (14) | 0.0029 (15) |
O2A | 0.0352 (18) | 0.0267 (18) | 0.0330 (19) | 0.0012 (15) | 0.0075 (14) | 0.0009 (16) |
O4B | 0.0396 (19) | 0.0248 (18) | 0.0348 (19) | −0.0027 (16) | 0.0042 (15) | 0.0000 (16) |
O2B | 0.0351 (18) | 0.033 (2) | 0.0295 (18) | 0.0041 (16) | 0.0043 (14) | 0.0006 (17) |
O1B | 0.051 (2) | 0.039 (2) | 0.0299 (19) | 0.0128 (19) | 0.0091 (16) | 0.0017 (18) |
O4A | 0.040 (2) | 0.0189 (18) | 0.042 (2) | −0.0008 (15) | 0.0019 (17) | 0.0009 (16) |
N2A | 0.036 (2) | 0.023 (2) | 0.024 (2) | −0.0014 (17) | 0.0057 (17) | 0.0018 (17) |
N3A | 0.038 (2) | 0.020 (2) | 0.025 (2) | 0.0007 (18) | −0.0017 (18) | −0.0017 (18) |
N2B | 0.039 (2) | 0.025 (2) | 0.027 (2) | 0.0054 (18) | 0.0066 (17) | 0.0005 (18) |
N3B | 0.048 (3) | 0.019 (2) | 0.031 (2) | −0.0027 (19) | 0.0116 (19) | 0.0002 (18) |
NA | 0.034 (2) | 0.030 (2) | 0.034 (2) | −0.0018 (19) | 0.0045 (18) | 0.004 (2) |
N1B | 0.044 (2) | 0.035 (2) | 0.031 (2) | 0.009 (2) | 0.0056 (19) | 0.000 (2) |
C10A | 0.035 (2) | 0.024 (2) | 0.027 (2) | 0.000 (2) | 0.006 (2) | −0.002 (2) |
C34A | 0.039 (5) | 0.036 (6) | 0.052 (8) | 0.003 (5) | −0.001 (5) | 0.002 (6) |
C35A | 0.048 (6) | 0.056 (8) | 0.067 (9) | 0.010 (6) | 0.012 (6) | 0.007 (7) |
C37A | 0.042 (6) | 0.079 (9) | 0.069 (10) | −0.016 (6) | 0.000 (6) | −0.026 (9) |
C38A | 0.048 (6) | 0.053 (8) | 0.057 (8) | −0.012 (5) | 0.006 (6) | −0.008 (7) |
C31A | 0.039 (3) | 0.024 (3) | 0.026 (2) | −0.001 (2) | 0.002 (2) | −0.003 (2) |
C1A | 0.033 (2) | 0.023 (2) | 0.023 (2) | −0.003 (2) | 0.0023 (18) | −0.001 (2) |
C10B | 0.036 (3) | 0.031 (3) | 0.028 (3) | 0.004 (2) | 0.008 (2) | 0.003 (2) |
C9A | 0.035 (3) | 0.026 (3) | 0.028 (2) | 0.001 (2) | 0.007 (2) | −0.004 (2) |
C3A | 0.039 (3) | 0.024 (2) | 0.031 (3) | −0.005 (2) | 0.004 (2) | 0.001 (2) |
C5A | 0.036 (3) | 0.034 (3) | 0.033 (3) | −0.001 (2) | 0.006 (2) | 0.002 (2) |
C21B | 0.039 (3) | 0.027 (3) | 0.035 (3) | 0.006 (2) | 0.002 (2) | 0.006 (2) |
C33B | 0.036 (2) | 0.024 (3) | 0.031 (3) | −0.004 (2) | 0.009 (2) | 0.002 (2) |
C9B | 0.034 (3) | 0.029 (3) | 0.036 (3) | 0.004 (2) | 0.008 (2) | 0.002 (2) |
C8B | 0.045 (3) | 0.037 (3) | 0.033 (3) | 0.005 (3) | 0.012 (2) | −0.002 (3) |
C7B | 0.053 (3) | 0.038 (3) | 0.041 (3) | 0.011 (3) | 0.012 (3) | −0.006 (3) |
C2A | 0.038 (3) | 0.027 (3) | 0.029 (2) | 0.001 (2) | 0.005 (2) | 0.000 (2) |
C38B | 0.043 (3) | 0.029 (3) | 0.036 (3) | −0.004 (2) | 0.012 (2) | −0.003 (2) |
C32A | 0.046 (3) | 0.034 (3) | 0.029 (3) | −0.001 (2) | 0.006 (2) | 0.000 (2) |
C6A | 0.036 (3) | 0.034 (3) | 0.037 (3) | 0.009 (2) | 0.005 (2) | 0.004 (3) |
C2B | 0.038 (3) | 0.029 (3) | 0.034 (3) | 0.008 (2) | 0.007 (2) | −0.002 (2) |
C5B | 0.040 (3) | 0.042 (3) | 0.034 (3) | 0.006 (3) | 0.005 (2) | 0.003 (3) |
C1B | 0.037 (3) | 0.026 (3) | 0.031 (3) | 0.002 (2) | 0.008 (2) | 0.002 (2) |
C4A | 0.040 (3) | 0.031 (3) | 0.027 (2) | −0.002 (2) | 0.007 (2) | −0.001 (2) |
C31B | 0.036 (3) | 0.026 (3) | 0.029 (2) | 0.000 (2) | 0.007 (2) | −0.001 (2) |
C8A | 0.034 (3) | 0.030 (3) | 0.033 (3) | 0.003 (2) | 0.007 (2) | 0.008 (2) |
C34B | 0.042 (3) | 0.025 (3) | 0.037 (3) | −0.002 (2) | 0.009 (2) | −0.002 (2) |
C4B | 0.042 (3) | 0.028 (3) | 0.031 (3) | 0.001 (2) | 0.008 (2) | −0.001 (2) |
C22B | 0.040 (3) | 0.037 (3) | 0.049 (3) | 0.002 (2) | 0.012 (3) | 0.005 (3) |
C7A | 0.042 (3) | 0.039 (3) | 0.035 (3) | 0.004 (3) | 0.008 (2) | 0.006 (3) |
C35B | 0.040 (3) | 0.031 (3) | 0.039 (3) | −0.003 (2) | 0.003 (2) | 0.002 (2) |
C21A | 0.042 (3) | 0.031 (3) | 0.040 (3) | 0.000 (2) | 0.015 (2) | 0.002 (2) |
C22A | 0.044 (3) | 0.031 (3) | 0.044 (3) | 0.000 (2) | 0.014 (2) | −0.003 (3) |
C3B | 0.042 (3) | 0.030 (3) | 0.030 (3) | 0.001 (2) | 0.007 (2) | −0.003 (2) |
C32B | 0.039 (3) | 0.047 (3) | 0.039 (3) | −0.002 (3) | 0.008 (2) | 0.002 (3) |
C37B | 0.057 (4) | 0.038 (3) | 0.034 (3) | −0.007 (3) | 0.012 (3) | −0.003 (3) |
C36B | 0.050 (3) | 0.042 (3) | 0.033 (3) | −0.013 (3) | 0.003 (2) | 0.002 (3) |
C6B | 0.043 (3) | 0.042 (3) | 0.046 (3) | 0.012 (3) | 0.008 (3) | 0.005 (3) |
C33A | 0.038 (3) | 0.033 (3) | 0.031 (3) | −0.001 (2) | 0.005 (2) | 0.002 (2) |
C34D | 0.042 (6) | 0.075 (12) | 0.036 (7) | 0.009 (7) | 0.007 (5) | −0.002 (8) |
C35D | 0.043 (6) | 0.071 (11) | 0.043 (6) | 0.023 (7) | 0.012 (5) | 0.017 (7) |
C36A | 0.038 (3) | 0.078 (5) | 0.062 (4) | 0.009 (3) | 0.005 (3) | 0.019 (4) |
C37D | 0.044 (6) | 0.042 (8) | 0.052 (8) | 0.001 (6) | −0.002 (6) | 0.001 (7) |
C38D | 0.040 (6) | 0.042 (9) | 0.048 (8) | −0.004 (6) | −0.003 (5) | −0.015 (7) |
Geometric parameters (Å, º) top
P1A—O4A | 1.479 (4) | C33B—C31B | 1.523 (7) |
P1A—O2A | 1.590 (4) | C9B—C8B | 1.397 (8) |
P1A—N3A | 1.618 (4) | C9B—C4B | 1.411 (7) |
P1A—C1A | 1.798 (5) | C8B—C7B | 1.377 (8) |
P1B—O4B | 1.483 (4) | C8B—H8B | 0.9300 |
P1B—O2B | 1.581 (4) | C7B—C6B | 1.408 (9) |
P1B—N3B | 1.617 (5) | C7B—H7B | 0.9300 |
P1B—C1B | 1.798 (5) | C2A—H2A | 0.9300 |
S1A—C4A | 1.737 (6) | C38B—C37B | 1.389 (8) |
S1A—C3A | 1.739 (5) | C38B—H38B | 0.9300 |
S1B—C3B | 1.733 (6) | C32A—H32A | 0.9600 |
S1B—C4B | 1.743 (6) | C32A—H32B | 0.9600 |
O1A—C10A | 1.227 (6) | C32A—H32C | 0.9600 |
O2A—C21A | 1.455 (6) | C6A—C7A | 1.388 (8) |
O2B—C21B | 1.450 (6) | C6A—H6A | 0.9300 |
O1B—C10B | 1.220 (6) | C2B—C1B | 1.377 (8) |
N2A—C3A | 1.376 (7) | C2B—H2B | 0.9300 |
N2A—C9A | 1.418 (7) | C5B—C4B | 1.375 (8) |
N2A—C10A | 1.434 (7) | C5B—C6B | 1.388 (9) |
N3A—C31A | 1.474 (6) | C5B—H5B | 0.9300 |
N3A—H3A | 0.90 (7) | C31B—C32B | 1.529 (7) |
N2B—C3B | 1.388 (7) | C31B—H31B | 0.9800 |
N2B—C9B | 1.410 (7) | C8A—C7A | 1.391 (8) |
N2B—C10B | 1.429 (6) | C8A—H8A | 0.9300 |
N3B—C31B | 1.469 (7) | C34B—C35B | 1.389 (8) |
N3B—H3B | 0.89 (9) | C34B—H34B | 0.9300 |
NA—C3A | 1.309 (7) | C22B—H22D | 0.9600 |
NA—C2A | 1.351 (7) | C22B—H22E | 0.9600 |
N1B—C3B | 1.302 (8) | C22B—H22F | 0.9600 |
N1B—C2B | 1.362 (7) | C7A—H7A | 0.9300 |
C10A—C1A | 1.432 (7) | C35B—C36B | 1.377 (9) |
C34A—C35A | 1.399 (17) | C35B—H35B | 0.9300 |
C34A—C33A | 1.413 (14) | C21A—C22A | 1.514 (8) |
C34A—H34A | 0.9300 | C21A—H21A | 0.9700 |
C35A—C36A | 1.515 (18) | C21A—H21B | 0.9700 |
C35A—H35A | 0.9300 | C22A—H22A | 0.9600 |
C37A—C36A | 1.29 (2) | C22A—H22B | 0.9600 |
C37A—C38A | 1.39 (2) | C22A—H22C | 0.9600 |
C37A—H37A | 0.9300 | C32B—H32D | 0.9600 |
C38A—C33A | 1.354 (14) | C32B—H32E | 0.9600 |
C38A—H38A | 0.9300 | C32B—H32F | 0.9600 |
C31A—C33A | 1.522 (7) | C37B—C36B | 1.388 (9) |
C31A—C32A | 1.527 (7) | C37B—H37B | 0.9300 |
C31A—H31A | 0.9800 | C36B—H36B | 0.9300 |
C1A—C2A | 1.376 (7) | C6B—H6B | 0.9300 |
C10B—C1B | 1.450 (7) | C33A—C34D | 1.360 (15) |
C9A—C8A | 1.393 (7) | C33A—C38D | 1.411 (14) |
C9A—C4A | 1.403 (8) | C34D—C35D | 1.39 (2) |
C5A—C6A | 1.391 (8) | C34D—H34D | 0.9300 |
C5A—C4A | 1.400 (8) | C35D—C36A | 1.272 (18) |
C5A—H5A | 0.9300 | C35D—H35D | 0.9300 |
C21B—C22B | 1.501 (8) | C36A—C37D | 1.46 (2) |
C21B—H21C | 0.9700 | C36A—H36A | 0.9300 |
C21B—H21D | 0.9700 | C37D—C38D | 1.40 (2) |
C33B—C38B | 1.390 (8) | C37D—H37D | 0.9300 |
C33B—C34B | 1.395 (8) | C38D—H38D | 0.9300 |
| | | |
O4A—P1A—O2A | 115.5 (2) | H32B—C32A—H32C | 109.5 |
O4A—P1A—N3A | 111.3 (2) | C7A—C6A—C5A | 120.9 (5) |
O2A—P1A—N3A | 106.1 (2) | C7A—C6A—H6A | 119.5 |
O4A—P1A—C1A | 112.6 (2) | C5A—C6A—H6A | 119.5 |
O2A—P1A—C1A | 100.3 (2) | N1B—C2B—C1B | 124.9 (5) |
N3A—P1A—C1A | 110.3 (2) | N1B—C2B—H2B | 117.6 |
O4B—P1B—O2B | 117.6 (2) | C1B—C2B—H2B | 117.6 |
O4B—P1B—N3B | 111.8 (2) | C4B—C5B—C6B | 118.6 (5) |
O2B—P1B—N3B | 104.5 (2) | C4B—C5B—H5B | 120.7 |
O4B—P1B—C1B | 111.7 (2) | C6B—C5B—H5B | 120.7 |
O2B—P1B—C1B | 97.5 (2) | C2B—C1B—C10B | 120.4 (5) |
N3B—P1B—C1B | 112.9 (2) | C2B—C1B—P1B | 122.1 (4) |
C4A—S1A—C3A | 90.8 (3) | C10B—C1B—P1B | 117.4 (4) |
C3B—S1B—C4B | 91.1 (3) | C5A—C4A—C9A | 120.8 (5) |
C21A—O2A—P1A | 117.6 (3) | C5A—C4A—S1A | 126.8 (4) |
C21B—O2B—P1B | 121.5 (3) | C9A—C4A—S1A | 112.4 (4) |
C3A—N2A—C9A | 113.7 (4) | N3B—C31B—C33B | 112.3 (4) |
C3A—N2A—C10A | 120.6 (4) | N3B—C31B—C32B | 110.8 (5) |
C9A—N2A—C10A | 125.7 (4) | C33B—C31B—C32B | 111.0 (4) |
C31A—N3A—P1A | 124.2 (4) | N3B—C31B—H31B | 107.5 |
C31A—N3A—H3A | 118 (4) | C33B—C31B—H31B | 107.5 |
P1A—N3A—H3A | 116 (4) | C32B—C31B—H31B | 107.5 |
C3B—N2B—C9B | 113.4 (4) | C7A—C8A—C9A | 117.4 (5) |
C3B—N2B—C10B | 120.7 (4) | C7A—C8A—H8A | 121.3 |
C9B—N2B—C10B | 125.9 (4) | C9A—C8A—H8A | 121.3 |
C31B—N3B—P1B | 123.3 (4) | C35B—C34B—C33B | 120.3 (5) |
C31B—N3B—H3B | 113 (5) | C35B—C34B—H34B | 119.9 |
P1B—N3B—H3B | 122 (5) | C33B—C34B—H34B | 119.9 |
C3A—NA—C2A | 114.8 (5) | C5B—C4B—C9B | 121.2 (5) |
C3B—N1B—C2B | 114.8 (5) | C5B—C4B—S1B | 127.1 (4) |
O1A—C10A—C1A | 126.7 (5) | C9B—C4B—S1B | 111.8 (4) |
O1A—C10A—N2A | 120.2 (4) | C21B—C22B—H22D | 109.5 |
C1A—C10A—N2A | 113.0 (4) | C21B—C22B—H22E | 109.5 |
C35A—C34A—C33A | 121.2 (12) | H22D—C22B—H22E | 109.5 |
C35A—C34A—H34A | 119.4 | C21B—C22B—H22F | 109.5 |
C33A—C34A—H34A | 119.4 | H22D—C22B—H22F | 109.5 |
C34A—C35A—C36A | 116.0 (12) | H22E—C22B—H22F | 109.5 |
C34A—C35A—H35A | 122.0 | C6A—C7A—C8A | 122.0 (6) |
C36A—C35A—H35A | 122.0 | C6A—C7A—H7A | 119.0 |
C36A—C37A—C38A | 121.7 (13) | C8A—C7A—H7A | 119.0 |
C36A—C37A—H37A | 119.1 | C36B—C35B—C34B | 120.7 (6) |
C38A—C37A—H37A | 119.1 | C36B—C35B—H35B | 119.6 |
C33A—C38A—C37A | 122.7 (14) | C34B—C35B—H35B | 119.6 |
C33A—C38A—H38A | 118.7 | O2A—C21A—C22A | 110.2 (5) |
C37A—C38A—H38A | 118.7 | O2A—C21A—H21A | 109.6 |
N3A—C31A—C33A | 111.0 (4) | C22A—C21A—H21A | 109.6 |
N3A—C31A—C32A | 111.0 (4) | O2A—C21A—H21B | 109.6 |
C33A—C31A—C32A | 111.3 (4) | C22A—C21A—H21B | 109.6 |
N3A—C31A—H31A | 107.8 | H21A—C21A—H21B | 108.1 |
C33A—C31A—H31A | 107.8 | C21A—C22A—H22A | 109.5 |
C32A—C31A—H31A | 107.8 | C21A—C22A—H22B | 109.5 |
C2A—C1A—C10A | 120.1 (5) | H22A—C22A—H22B | 109.5 |
C2A—C1A—P1A | 121.7 (4) | C21A—C22A—H22C | 109.5 |
C10A—C1A—P1A | 118.2 (4) | H22A—C22A—H22C | 109.5 |
O1B—C10B—N2B | 120.7 (5) | H22B—C22A—H22C | 109.5 |
O1B—C10B—C1B | 126.9 (5) | N1B—C3B—N2B | 126.2 (5) |
N2B—C10B—C1B | 112.4 (5) | N1B—C3B—S1B | 121.7 (4) |
C8A—C9A—C4A | 121.1 (5) | N2B—C3B—S1B | 112.0 (4) |
C8A—C9A—N2A | 127.8 (5) | C31B—C32B—H32D | 109.5 |
C4A—C9A—N2A | 111.0 (5) | C31B—C32B—H32E | 109.5 |
NA—C3A—N2A | 125.9 (5) | H32D—C32B—H32E | 109.5 |
NA—C3A—S1A | 122.2 (4) | C31B—C32B—H32F | 109.5 |
N2A—C3A—S1A | 111.9 (4) | H32D—C32B—H32F | 109.5 |
C6A—C5A—C4A | 117.8 (5) | H32E—C32B—H32F | 109.5 |
C6A—C5A—H5A | 121.1 | C36B—C37B—C38B | 119.1 (6) |
C4A—C5A—H5A | 121.1 | C36B—C37B—H37B | 120.4 |
O2B—C21B—C22B | 108.7 (4) | C38B—C37B—H37B | 120.4 |
O2B—C21B—H21C | 110.0 | C35B—C36B—C37B | 120.0 (5) |
C22B—C21B—H21C | 110.0 | C35B—C36B—H36B | 120.0 |
O2B—C21B—H21D | 110.0 | C37B—C36B—H36B | 120.0 |
C22B—C21B—H21D | 110.0 | C5B—C6B—C7B | 120.6 (6) |
H21C—C21B—H21D | 108.3 | C5B—C6B—H6B | 119.7 |
C38B—C33B—C34B | 118.2 (5) | C7B—C6B—H6B | 119.7 |
C38B—C33B—C31B | 119.6 (5) | C34D—C33A—C38D | 116.5 (10) |
C34B—C33B—C31B | 122.2 (5) | C38A—C33A—C34A | 118.4 (9) |
C8B—C9B—N2B | 128.2 (5) | C38A—C33A—C31A | 122.4 (8) |
C8B—C9B—C4B | 120.1 (5) | C34D—C33A—C31A | 125.9 (8) |
N2B—C9B—C4B | 111.6 (5) | C38D—C33A—C31A | 117.6 (8) |
C7B—C8B—C9B | 118.5 (5) | C34A—C33A—C31A | 119.2 (7) |
C7B—C8B—H8B | 120.7 | C33A—C34D—C35D | 122.9 (13) |
C9B—C8B—H8B | 120.7 | C33A—C34D—H34D | 118.6 |
C8B—C7B—C6B | 121.0 (6) | C35D—C34D—H34D | 118.6 |
C8B—C7B—H7B | 119.5 | C36A—C35D—C34D | 121.7 (13) |
C6B—C7B—H7B | 119.5 | C36A—C35D—H35D | 119.1 |
NA—C2A—C1A | 125.4 (5) | C34D—C35D—H35D | 119.1 |
NA—C2A—H2A | 117.3 | C35D—C36A—C37D | 120.2 (10) |
C1A—C2A—H2A | 117.3 | C37A—C36A—C35A | 120.0 (9) |
C37B—C38B—C33B | 121.7 (6) | C37A—C36A—H36A | 120.0 |
C37B—C38B—H38B | 119.1 | C35A—C36A—H36A | 120.0 |
C33B—C38B—H38B | 119.1 | C38D—C37D—C36A | 117.6 (13) |
C31A—C32A—H32A | 109.5 | C38D—C37D—H37D | 121.2 |
C31A—C32A—H32B | 109.5 | C36A—C37D—H37D | 121.2 |
H32A—C32A—H32B | 109.5 | C37D—C38D—C33A | 121.0 (14) |
C31A—C32A—H32C | 109.5 | C37D—C38D—H38D | 119.5 |
H32A—C32A—H32C | 109.5 | C33A—C38D—H38D | 119.5 |
| | | |
O4A—P1A—O2A—C21A | −63.2 (4) | N3B—P1B—C1B—C2B | 101.7 (5) |
N3A—P1A—O2A—C21A | 60.6 (4) | O4B—P1B—C1B—C10B | 44.8 (5) |
C1A—P1A—O2A—C21A | 175.5 (4) | O2B—P1B—C1B—C10B | 168.5 (4) |
O4B—P1B—O2B—C21B | −57.8 (5) | N3B—P1B—C1B—C10B | −82.2 (5) |
N3B—P1B—O2B—C21B | 66.8 (4) | C6A—C5A—C4A—C9A | −0.2 (8) |
C1B—P1B—O2B—C21B | −177.1 (4) | C6A—C5A—C4A—S1A | 177.1 (4) |
O4A—P1A—N3A—C31A | −20.2 (5) | C8A—C9A—C4A—C5A | 0.3 (8) |
O2A—P1A—N3A—C31A | −146.6 (4) | N2A—C9A—C4A—C5A | 177.9 (5) |
C1A—P1A—N3A—C31A | 105.6 (4) | C8A—C9A—C4A—S1A | −177.3 (4) |
O4B—P1B—N3B—C31B | −31.0 (5) | N2A—C9A—C4A—S1A | 0.3 (6) |
O2B—P1B—N3B—C31B | −159.3 (4) | C3A—S1A—C4A—C5A | −175.6 (5) |
C1B—P1B—N3B—C31B | 95.9 (4) | C3A—S1A—C4A—C9A | 1.8 (4) |
C3A—N2A—C10A—O1A | 178.2 (5) | P1B—N3B—C31B—C33B | 114.7 (5) |
C9A—N2A—C10A—O1A | −0.5 (8) | P1B—N3B—C31B—C32B | −120.6 (5) |
C3A—N2A—C10A—C1A | −2.8 (6) | C38B—C33B—C31B—N3B | −150.2 (5) |
C9A—N2A—C10A—C1A | 178.5 (4) | C34B—C33B—C31B—N3B | 31.0 (7) |
C33A—C34A—C35A—C36A | 0 (2) | C38B—C33B—C31B—C32B | 85.2 (6) |
C36A—C37A—C38A—C33A | 1 (3) | C34B—C33B—C31B—C32B | −93.7 (6) |
P1A—N3A—C31A—C33A | 122.2 (5) | C4A—C9A—C8A—C7A | −0.5 (8) |
P1A—N3A—C31A—C32A | −113.5 (5) | N2A—C9A—C8A—C7A | −177.6 (5) |
O1A—C10A—C1A—C2A | 177.6 (5) | C38B—C33B—C34B—C35B | 0.4 (8) |
N2A—C10A—C1A—C2A | −1.3 (7) | C31B—C33B—C34B—C35B | 179.2 (5) |
O1A—C10A—C1A—P1A | −4.7 (7) | C6B—C5B—C4B—C9B | −0.5 (9) |
N2A—C10A—C1A—P1A | 176.3 (3) | C6B—C5B—C4B—S1B | 179.4 (5) |
O4A—P1A—C1A—C2A | 124.6 (4) | C8B—C9B—C4B—C5B | −0.2 (9) |
O2A—P1A—C1A—C2A | −112.1 (4) | N2B—C9B—C4B—C5B | 178.3 (5) |
N3A—P1A—C1A—C2A | −0.4 (5) | C8B—C9B—C4B—S1B | 179.9 (5) |
O4A—P1A—C1A—C10A | −53.0 (4) | N2B—C9B—C4B—S1B | −1.5 (6) |
O2A—P1A—C1A—C10A | 70.3 (4) | C3B—S1B—C4B—C5B | −179.1 (6) |
N3A—P1A—C1A—C10A | −178.1 (4) | C3B—S1B—C4B—C9B | 0.7 (5) |
C3B—N2B—C10B—O1B | 174.5 (5) | C5A—C6A—C7A—C8A | −0.5 (9) |
C9B—N2B—C10B—O1B | −7.0 (8) | C9A—C8A—C7A—C6A | 0.6 (9) |
C3B—N2B—C10B—C1B | −5.5 (7) | C33B—C34B—C35B—C36B | 0.3 (8) |
C9B—N2B—C10B—C1B | 173.0 (5) | P1A—O2A—C21A—C22A | −110.7 (5) |
C3A—N2A—C9A—C8A | 174.4 (5) | C2B—N1B—C3B—N2B | 5.8 (9) |
C10A—N2A—C9A—C8A | −6.8 (8) | C2B—N1B—C3B—S1B | −173.2 (4) |
C3A—N2A—C9A—C4A | −3.0 (6) | C9B—N2B—C3B—N1B | 179.7 (6) |
C10A—N2A—C9A—C4A | 175.8 (5) | C10B—N2B—C3B—N1B | −1.6 (9) |
C2A—NA—C3A—N2A | −2.5 (8) | C9B—N2B—C3B—S1B | −1.2 (6) |
C2A—NA—C3A—S1A | 177.0 (4) | C10B—N2B—C3B—S1B | 177.5 (4) |
C9A—N2A—C3A—NA | −176.1 (5) | C4B—S1B—C3B—N1B | 179.4 (5) |
C10A—N2A—C3A—NA | 5.1 (8) | C4B—S1B—C3B—N2B | 0.3 (4) |
C9A—N2A—C3A—S1A | 4.4 (5) | C33B—C38B—C37B—C36B | 0.1 (9) |
C10A—N2A—C3A—S1A | −174.5 (4) | C34B—C35B—C36B—C37B | −0.7 (9) |
C4A—S1A—C3A—NA | 176.9 (5) | C38B—C37B—C36B—C35B | 0.5 (9) |
C4A—S1A—C3A—N2A | −3.5 (4) | C4B—C5B—C6B—C7B | 1.3 (10) |
P1B—O2B—C21B—C22B | 110.8 (5) | C8B—C7B—C6B—C5B | −1.4 (10) |
C3B—N2B—C9B—C8B | −179.9 (6) | C37A—C38A—C33A—C34A | 1 (2) |
C10B—N2B—C9B—C8B | 1.6 (9) | C37A—C38A—C33A—C31A | −179.0 (13) |
C3B—N2B—C9B—C4B | 1.7 (7) | C35A—C34A—C33A—C38A | −1.8 (18) |
C10B—N2B—C9B—C4B | −176.8 (5) | C35A—C34A—C33A—C31A | 178.6 (11) |
N2B—C9B—C8B—C7B | −178.2 (6) | N3A—C31A—C33A—C38A | −130.1 (11) |
C4B—C9B—C8B—C7B | 0.1 (9) | C32A—C31A—C33A—C38A | 105.7 (11) |
C9B—C8B—C7B—C6B | 0.7 (10) | N3A—C31A—C33A—C34D | 7.6 (15) |
C3A—NA—C2A—C1A | −2.1 (8) | C32A—C31A—C33A—C34D | −116.6 (14) |
C10A—C1A—C2A—NA | 4.0 (8) | N3A—C31A—C33A—C38D | −172.9 (10) |
P1A—C1A—C2A—NA | −173.5 (4) | C32A—C31A—C33A—C38D | 62.9 (11) |
C34B—C33B—C38B—C37B | −0.6 (8) | N3A—C31A—C33A—C34A | 49.5 (10) |
C31B—C33B—C38B—C37B | −179.5 (5) | C32A—C31A—C33A—C34A | −74.6 (10) |
C4A—C5A—C6A—C7A | 0.3 (8) | C38D—C33A—C34D—C35D | 2 (3) |
C3B—N1B—C2B—C1B | −2.5 (9) | C31A—C33A—C34D—C35D | −178.2 (15) |
N1B—C2B—C1B—C10B | −4.7 (9) | C33A—C34D—C35D—C36A | −5 (3) |
N1B—C2B—C1B—P1B | 171.2 (5) | C34D—C35D—C36A—C37D | 3 (3) |
O1B—C10B—C1B—C2B | −171.7 (6) | C38A—C37A—C36A—C35A | −3 (2) |
N2B—C10B—C1B—C2B | 8.3 (8) | C34A—C35A—C36A—C37A | 3 (2) |
O1B—C10B—C1B—P1B | 12.1 (8) | C35D—C36A—C37D—C38D | 0 (2) |
N2B—C10B—C1B—P1B | −167.9 (4) | C36A—C37D—C38D—C33A | −2 (2) |
O4B—P1B—C1B—C2B | −131.2 (5) | C34D—C33A—C38D—C37D | 1 (2) |
O2B—P1B—C1B—C2B | −7.5 (5) | C31A—C33A—C38D—C37D | −178.9 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O4Ai | 0.90 (7) | 1.88 (7) | 2.774 (6) | 175 (5) |
N3B—H3B···O4Bi | 0.89 (9) | 2.31 (9) | 3.070 (6) | 144 (7) |
N3B—H3B···O1Bi | 0.89 (9) | 2.71 (8) | 3.419 (6) | 137 (6) |
Symmetry code: (i) x, y+1, z. |
Diethyl
(4-isopropyl-2-oxo-3,4-dihydro-2
H-benzo[4,5]thiazolo[3,2-
a]pyrimidin-3-yl)phosphonate (II)
top
Crystal data top
C18H25N2O4PS | Z = 2 |
Mr = 396.43 | F(000) = 420 |
Triclinic, P1 | Dx = 1.369 Mg m−3 |
a = 9.6275 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 10.0903 (5) Å | Cell parameters from 10170 reflections |
c = 11.8585 (6) Å | θ = 4.3–79.0° |
α = 65.779 (5)° | µ = 2.51 mm−1 |
β = 67.462 (5)° | T = 100 K |
γ = 74.329 (4)° | Prism, colourless |
V = 961.59 (9) Å3 | 0.18 × 0.08 × 0.07 mm |
Data collection top
XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer | 3490 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 3290 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.051 |
ω scans | θmax = 68.0°, θmin = 4.3° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | h = −11→10 |
Tmin = 0.390, Tmax = 1.000 | k = −12→12 |
14969 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | 417 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.1232P)2 + 0.414P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3490 reflections | Δρmax = 0.92 e Å−3 |
260 parameters | Δρmin = −0.56 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O2 | 0.81925 (19) | 0.65340 (18) | 0.49949 (16) | 0.0341 (4) | |
C21A | 0.8125 (12) | 0.5799 (9) | 0.4168 (8) | 0.038 (2) | 0.614 (13) |
H21A | 0.749241 | 0.643824 | 0.360433 | 0.046* | 0.614 (13) |
H21B | 0.915504 | 0.555336 | 0.361139 | 0.046* | 0.614 (13) |
C22A | 0.7441 (8) | 0.4455 (7) | 0.5083 (5) | 0.0456 (18) | 0.614 (13) |
H22A | 0.745785 | 0.386210 | 0.459705 | 0.068* | 0.614 (13) |
H22B | 0.638963 | 0.472092 | 0.556694 | 0.068* | 0.614 (13) |
H22C | 0.802158 | 0.388792 | 0.569318 | 0.068* | 0.614 (13) |
C21B | 0.8263 (18) | 0.5421 (17) | 0.4452 (17) | 0.046 (4) | 0.386 (13) |
H21C | 0.874911 | 0.578575 | 0.349805 | 0.056* | 0.386 (13) |
H21D | 0.888905 | 0.450743 | 0.482802 | 0.056* | 0.386 (13) |
C22B | 0.6726 (12) | 0.5108 (11) | 0.4749 (10) | 0.052 (3) | 0.386 (13) |
H22E | 0.679401 | 0.435875 | 0.439681 | 0.078* | 0.386 (13) |
H22F | 0.611691 | 0.600628 | 0.435319 | 0.078* | 0.386 (13) |
H22G | 0.624471 | 0.474962 | 0.569346 | 0.078* | 0.386 (13) |
S1 | 0.71009 (5) | 0.44044 (5) | 0.85469 (5) | 0.0251 (2) | |
P1 | 0.80758 (6) | 0.82491 (6) | 0.43848 (5) | 0.0266 (2) | |
O3 | 0.96784 (17) | 0.85037 (19) | 0.33184 (15) | 0.0354 (4) | |
O1 | 1.04350 (16) | 0.82467 (17) | 0.60324 (15) | 0.0307 (4) | |
O4 | 0.67918 (18) | 0.9035 (2) | 0.38820 (16) | 0.0354 (4) | |
N1 | 0.62591 (19) | 0.71244 (18) | 0.74315 (16) | 0.0216 (4) | |
N2 | 0.88572 (19) | 0.6535 (2) | 0.73848 (17) | 0.0249 (4) | |
C2 | 0.6406 (2) | 0.8699 (2) | 0.6706 (2) | 0.0221 (4) | |
H2 | 0.563554 | 0.914590 | 0.623145 | 0.026* | |
C3 | 0.4988 (2) | 0.6432 (2) | 0.77999 (19) | 0.0221 (4) | |
C1 | 0.8007 (2) | 0.8747 (2) | 0.5708 (2) | 0.0232 (4) | |
H1 | 0.821173 | 0.978773 | 0.532883 | 0.028* | |
C9 | 0.7492 (2) | 0.6204 (2) | 0.77049 (19) | 0.0220 (4) | |
C4 | 0.3606 (2) | 0.7071 (2) | 0.7571 (2) | 0.0245 (4) | |
H4 | 0.342393 | 0.809319 | 0.711720 | 0.029* | |
C5 | 0.2497 (2) | 0.6174 (2) | 0.8024 (2) | 0.0262 (5) | |
H5 | 0.154463 | 0.659825 | 0.787797 | 0.031* | |
C24 | 0.6142 (2) | 0.9507 (2) | 0.7640 (2) | 0.0254 (5) | |
H24 | 0.690428 | 0.904223 | 0.812131 | 0.030* | |
C10 | 0.9200 (2) | 0.7830 (2) | 0.6388 (2) | 0.0243 (5) | |
C6 | 0.2738 (2) | 0.4666 (2) | 0.8689 (2) | 0.0256 (5) | |
C8 | 0.5256 (2) | 0.4927 (2) | 0.8445 (2) | 0.0231 (4) | |
C7 | 0.4130 (2) | 0.4035 (2) | 0.8896 (2) | 0.0245 (4) | |
H7 | 0.431645 | 0.301067 | 0.933926 | 0.029* | |
C26 | 0.4555 (2) | 0.9407 (2) | 0.8627 (2) | 0.0265 (5) | |
H26A | 0.379613 | 0.992857 | 0.817445 | 0.040* | |
H26B | 0.445254 | 0.985378 | 0.925456 | 0.040* | |
H26C | 0.439759 | 0.837546 | 0.908709 | 0.040* | |
C31 | 0.9868 (3) | 0.9814 (3) | 0.2162 (2) | 0.0332 (5) | |
H31A | 1.012657 | 1.059338 | 0.232184 | 0.040* | |
H31B | 0.891546 | 1.018221 | 0.193032 | 0.040* | |
C25 | 0.6362 (3) | 1.1120 (3) | 0.6869 (2) | 0.0330 (5) | |
H25A | 0.743580 | 1.118905 | 0.636806 | 0.049* | |
H25B | 0.603876 | 1.165980 | 0.747086 | 0.049* | |
H25C | 0.575235 | 1.154410 | 0.627303 | 0.049* | |
C32 | 1.1119 (3) | 0.9411 (3) | 0.1086 (2) | 0.0386 (6) | |
H32A | 1.130507 | 1.028589 | 0.030145 | 0.058* | |
H32B | 1.083035 | 0.867402 | 0.090844 | 0.058* | |
H32C | 1.204467 | 0.900938 | 0.134132 | 0.058* | |
C61 | 0.1499 (3) | 0.3724 (3) | 0.9188 (2) | 0.0326 (5) | |
H61A | 0.069036 | 0.427771 | 0.879902 | 0.049* | |
H61B | 0.108379 | 0.344307 | 1.013667 | 0.049* | |
H61C | 0.192056 | 0.283986 | 0.895234 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0387 (10) | 0.0351 (9) | 0.0294 (9) | −0.0025 (7) | −0.0061 (7) | −0.0175 (7) |
C21A | 0.057 (4) | 0.031 (3) | 0.028 (3) | −0.003 (3) | −0.010 (2) | −0.015 (3) |
C22A | 0.064 (4) | 0.041 (3) | 0.039 (3) | −0.016 (3) | −0.013 (2) | −0.019 (2) |
C21B | 0.056 (5) | 0.050 (8) | 0.041 (8) | 0.008 (5) | −0.016 (5) | −0.031 (7) |
C22B | 0.069 (6) | 0.041 (5) | 0.058 (5) | −0.006 (4) | −0.028 (4) | −0.021 (4) |
S1 | 0.0200 (3) | 0.0230 (3) | 0.0276 (3) | 0.0021 (2) | −0.0077 (2) | −0.0070 (2) |
P1 | 0.0187 (3) | 0.0346 (4) | 0.0221 (3) | 0.0017 (2) | −0.0042 (2) | −0.0107 (3) |
O3 | 0.0211 (8) | 0.0465 (10) | 0.0248 (8) | 0.0036 (7) | −0.0027 (6) | −0.0082 (7) |
O1 | 0.0169 (7) | 0.0355 (9) | 0.0354 (9) | −0.0041 (6) | −0.0068 (6) | −0.0090 (7) |
O4 | 0.0218 (8) | 0.0525 (10) | 0.0311 (9) | 0.0042 (7) | −0.0106 (7) | −0.0171 (8) |
N1 | 0.0160 (8) | 0.0223 (9) | 0.0227 (9) | 0.0004 (7) | −0.0038 (7) | −0.0081 (7) |
N2 | 0.0165 (8) | 0.0293 (9) | 0.0261 (9) | 0.0017 (7) | −0.0058 (7) | −0.0106 (7) |
C2 | 0.0165 (10) | 0.0221 (10) | 0.0247 (10) | 0.0002 (7) | −0.0047 (8) | −0.0086 (8) |
C3 | 0.0172 (9) | 0.0260 (10) | 0.0215 (10) | −0.0020 (8) | −0.0029 (7) | −0.0099 (8) |
C1 | 0.0160 (10) | 0.0251 (10) | 0.0247 (10) | −0.0011 (8) | −0.0045 (8) | −0.0078 (8) |
C9 | 0.0178 (10) | 0.0252 (10) | 0.0208 (10) | 0.0027 (8) | −0.0053 (8) | −0.0098 (8) |
C4 | 0.0206 (10) | 0.0247 (10) | 0.0257 (10) | −0.0008 (8) | −0.0071 (8) | −0.0077 (8) |
C5 | 0.0186 (10) | 0.0322 (11) | 0.0270 (11) | −0.0011 (8) | −0.0068 (8) | −0.0111 (9) |
C24 | 0.0181 (10) | 0.0288 (11) | 0.0297 (11) | 0.0002 (8) | −0.0063 (8) | −0.0136 (9) |
C10 | 0.0158 (10) | 0.0284 (10) | 0.0270 (11) | 0.0019 (8) | −0.0044 (8) | −0.0131 (9) |
C6 | 0.0240 (10) | 0.0286 (11) | 0.0252 (11) | −0.0048 (8) | −0.0062 (8) | −0.0108 (8) |
C8 | 0.0202 (10) | 0.0243 (10) | 0.0230 (10) | 0.0013 (8) | −0.0061 (8) | −0.0096 (8) |
C7 | 0.0244 (10) | 0.0230 (10) | 0.0240 (10) | −0.0034 (8) | −0.0062 (8) | −0.0073 (8) |
C26 | 0.0206 (10) | 0.0322 (11) | 0.0273 (11) | 0.0004 (8) | −0.0063 (8) | −0.0143 (9) |
C31 | 0.0318 (12) | 0.0325 (12) | 0.0285 (12) | −0.0013 (9) | −0.0033 (9) | −0.0115 (9) |
C25 | 0.0281 (12) | 0.0296 (12) | 0.0410 (13) | −0.0033 (9) | −0.0047 (10) | −0.0180 (10) |
C32 | 0.0333 (13) | 0.0401 (13) | 0.0301 (12) | 0.0013 (10) | −0.0022 (10) | −0.0114 (10) |
C61 | 0.0285 (12) | 0.0338 (12) | 0.0357 (13) | −0.0095 (9) | −0.0097 (10) | −0.0090 (10) |
Geometric parameters (Å, º) top
O2—C21A | 1.479 (8) | C3—C4 | 1.389 (3) |
O2—C21B | 1.482 (12) | C3—C8 | 1.394 (3) |
O2—P1 | 1.5688 (17) | C1—C10 | 1.533 (3) |
C21A—C22A | 1.476 (8) | C1—H1 | 1.0000 |
C21A—H21A | 0.9900 | C4—C5 | 1.390 (3) |
C21A—H21B | 0.9900 | C4—H4 | 0.9500 |
C22A—H22A | 0.9800 | C5—C6 | 1.398 (3) |
C22A—H22B | 0.9800 | C5—H5 | 0.9500 |
C22A—H22C | 0.9800 | C24—C26 | 1.526 (3) |
C21B—C22B | 1.476 (13) | C24—C25 | 1.532 (3) |
C21B—H21C | 0.9900 | C24—H24 | 1.0000 |
C21B—H21D | 0.9900 | C6—C7 | 1.388 (3) |
C22B—H22E | 0.9800 | C6—C61 | 1.512 (3) |
C22B—H22F | 0.9800 | C8—C7 | 1.399 (3) |
C22B—H22G | 0.9800 | C7—H7 | 0.9500 |
S1—C9 | 1.740 (2) | C26—H26A | 0.9800 |
S1—C8 | 1.748 (2) | C26—H26B | 0.9800 |
P1—O4 | 1.4697 (16) | C26—H26C | 0.9800 |
P1—O3 | 1.5804 (16) | C31—C32 | 1.493 (3) |
P1—C1 | 1.807 (2) | C31—H31A | 0.9900 |
O3—C31 | 1.453 (3) | C31—H31B | 0.9900 |
O1—C10 | 1.228 (3) | C25—H25A | 0.9800 |
N1—C9 | 1.352 (3) | C25—H25B | 0.9800 |
N1—C3 | 1.407 (3) | C25—H25C | 0.9800 |
N1—C2 | 1.480 (3) | C32—H32A | 0.9800 |
N2—C9 | 1.317 (3) | C32—H32B | 0.9800 |
N2—C10 | 1.372 (3) | C32—H32C | 0.9800 |
C2—C24 | 1.541 (3) | C61—H61A | 0.9800 |
C2—C1 | 1.541 (3) | C61—H61B | 0.9800 |
C2—H2 | 1.0000 | C61—H61C | 0.9800 |
| | | |
C21A—O2—P1 | 115.3 (4) | N1—C9—S1 | 111.46 (15) |
C21B—O2—P1 | 131.3 (7) | C3—C4—C5 | 118.11 (19) |
C22A—C21A—O2 | 105.3 (6) | C3—C4—H4 | 120.9 |
C22A—C21A—H21A | 110.7 | C5—C4—H4 | 120.9 |
O2—C21A—H21A | 110.7 | C4—C5—C6 | 122.10 (19) |
C22A—C21A—H21B | 110.7 | C4—C5—H5 | 118.9 |
O2—C21A—H21B | 110.7 | C6—C5—H5 | 118.9 |
H21A—C21A—H21B | 108.8 | C26—C24—C25 | 109.65 (17) |
C21A—C22A—H22A | 109.5 | C26—C24—C2 | 111.37 (17) |
C21A—C22A—H22B | 109.5 | C25—C24—C2 | 110.02 (18) |
H22A—C22A—H22B | 109.5 | C26—C24—H24 | 108.6 |
C21A—C22A—H22C | 109.5 | C25—C24—H24 | 108.6 |
H22A—C22A—H22C | 109.5 | C2—C24—H24 | 108.6 |
H22B—C22A—H22C | 109.5 | O1—C10—N2 | 121.32 (19) |
C22B—C21B—O2 | 110.5 (10) | O1—C10—C1 | 120.34 (19) |
C22B—C21B—H21C | 109.5 | N2—C10—C1 | 118.33 (17) |
O2—C21B—H21C | 109.5 | C7—C6—C5 | 119.32 (19) |
C22B—C21B—H21D | 109.5 | C7—C6—C61 | 119.89 (19) |
O2—C21B—H21D | 109.5 | C5—C6—C61 | 120.80 (19) |
H21C—C21B—H21D | 108.1 | C3—C8—C7 | 120.78 (19) |
C21B—C22B—H22E | 109.5 | C3—C8—S1 | 111.11 (15) |
C21B—C22B—H22F | 109.5 | C7—C8—S1 | 128.10 (16) |
H22E—C22B—H22F | 109.5 | C6—C7—C8 | 119.11 (19) |
C21B—C22B—H22G | 109.5 | C6—C7—H7 | 120.4 |
H22E—C22B—H22G | 109.5 | C8—C7—H7 | 120.4 |
H22F—C22B—H22G | 109.5 | C24—C26—H26A | 109.5 |
C9—S1—C8 | 90.98 (10) | C24—C26—H26B | 109.5 |
O4—P1—O2 | 117.09 (10) | H26A—C26—H26B | 109.5 |
O4—P1—O3 | 113.67 (9) | C24—C26—H26C | 109.5 |
O2—P1—O3 | 102.87 (9) | H26A—C26—H26C | 109.5 |
O4—P1—C1 | 111.61 (10) | H26B—C26—H26C | 109.5 |
O2—P1—C1 | 102.45 (9) | O3—C31—C32 | 107.61 (19) |
O3—P1—C1 | 108.10 (10) | O3—C31—H31A | 110.2 |
C31—O3—P1 | 121.17 (14) | C32—C31—H31A | 110.2 |
C9—N1—C3 | 114.59 (17) | O3—C31—H31B | 110.2 |
C9—N1—C2 | 118.28 (17) | C32—C31—H31B | 110.2 |
C3—N1—C2 | 126.95 (16) | H31A—C31—H31B | 108.5 |
C9—N2—C10 | 116.44 (17) | C24—C25—H25A | 109.5 |
N1—C2—C24 | 110.70 (16) | C24—C25—H25B | 109.5 |
N1—C2—C1 | 105.68 (15) | H25A—C25—H25B | 109.5 |
C24—C2—C1 | 113.08 (17) | C24—C25—H25C | 109.5 |
N1—C2—H2 | 109.1 | H25A—C25—H25C | 109.5 |
C24—C2—H2 | 109.1 | H25B—C25—H25C | 109.5 |
C1—C2—H2 | 109.1 | C31—C32—H32A | 109.5 |
C4—C3—C8 | 120.57 (19) | C31—C32—H32B | 109.5 |
C4—C3—N1 | 127.69 (19) | H32A—C32—H32B | 109.5 |
C8—C3—N1 | 111.73 (18) | C31—C32—H32C | 109.5 |
C10—C1—C2 | 110.37 (16) | H32A—C32—H32C | 109.5 |
C10—C1—P1 | 114.24 (14) | H32B—C32—H32C | 109.5 |
C2—C1—P1 | 110.61 (14) | C6—C61—H61A | 109.5 |
C10—C1—H1 | 107.1 | C6—C61—H61B | 109.5 |
C2—C1—H1 | 107.1 | H61A—C61—H61B | 109.5 |
P1—C1—H1 | 107.1 | C6—C61—H61C | 109.5 |
N2—C9—N1 | 127.49 (19) | H61A—C61—H61C | 109.5 |
N2—C9—S1 | 121.03 (15) | H61B—C61—H61C | 109.5 |
| | | |
P1—O2—C21A—C22A | −150.4 (6) | C2—N1—C9—N2 | −0.9 (3) |
P1—O2—C21B—C22B | −91.5 (14) | C3—N1—C9—S1 | −4.0 (2) |
C21A—O2—P1—O4 | 52.1 (5) | C2—N1—C9—S1 | −179.46 (13) |
C21B—O2—P1—O4 | 56.3 (8) | C8—S1—C9—N2 | −175.96 (18) |
C21A—O2—P1—O3 | −73.3 (5) | C8—S1—C9—N1 | 2.70 (16) |
C21B—O2—P1—O3 | −69.1 (8) | C8—C3—C4—C5 | 1.2 (3) |
C21A—O2—P1—C1 | 174.5 (5) | N1—C3—C4—C5 | 179.97 (19) |
C21B—O2—P1—C1 | 178.8 (8) | C3—C4—C5—C6 | −0.3 (3) |
O4—P1—O3—C31 | 24.8 (2) | N1—C2—C24—C26 | −60.5 (2) |
O2—P1—O3—C31 | 152.35 (18) | C1—C2—C24—C26 | −178.90 (16) |
C1—P1—O3—C31 | −99.75 (18) | N1—C2—C24—C25 | 177.67 (16) |
C9—N1—C2—C24 | −85.6 (2) | C1—C2—C24—C25 | 59.3 (2) |
C3—N1—C2—C24 | 99.6 (2) | C9—N2—C10—O1 | 178.75 (19) |
C9—N1—C2—C1 | 37.2 (2) | C9—N2—C10—C1 | −2.0 (3) |
C3—N1—C2—C1 | −137.62 (19) | C2—C1—C10—O1 | −142.2 (2) |
C9—N1—C3—C4 | −175.4 (2) | P1—C1—C10—O1 | 92.5 (2) |
C2—N1—C3—C4 | −0.4 (3) | C2—C1—C10—N2 | 38.6 (2) |
C9—N1—C3—C8 | 3.4 (2) | P1—C1—C10—N2 | −86.8 (2) |
C2—N1—C3—C8 | 178.42 (18) | C4—C5—C6—C7 | −0.6 (3) |
N1—C2—C1—C10 | −52.7 (2) | C4—C5—C6—C61 | 179.0 (2) |
C24—C2—C1—C10 | 68.6 (2) | C4—C3—C8—C7 | −1.2 (3) |
N1—C2—C1—P1 | 74.73 (17) | N1—C3—C8—C7 | 179.82 (18) |
C24—C2—C1—P1 | −164.02 (14) | C4—C3—C8—S1 | 177.69 (16) |
O4—P1—C1—C10 | 172.81 (14) | N1—C3—C8—S1 | −1.2 (2) |
O2—P1—C1—C10 | 46.72 (17) | C9—S1—C8—C3 | −0.79 (16) |
O3—P1—C1—C10 | −61.47 (17) | C9—S1—C8—C7 | 178.1 (2) |
O4—P1—C1—C2 | 47.56 (17) | C5—C6—C7—C8 | 0.6 (3) |
O2—P1—C1—C2 | −78.54 (15) | C61—C6—C7—C8 | −179.03 (19) |
O3—P1—C1—C2 | 173.28 (13) | C3—C8—C7—C6 | 0.3 (3) |
C10—N2—C9—N1 | −19.3 (3) | S1—C8—C7—C6 | −178.41 (16) |
C10—N2—C9—S1 | 159.17 (15) | P1—O3—C31—C32 | −149.12 (18) |
C3—N1—C9—N2 | 174.55 (19) | | |
Selected intermolecular energies (kcal mol-1; 1 kcal mol-1 =
4.184 kJ mol-1) computed in (a) PIXELC and (b)
CrystalExplorer17.
Respective values are accompanied by the relevant intermolecular interactions
involved topMotif | Symmetry code | D | ECoul | Epol | Edisp | Erep | Etot | Interactions involved |
I A···A | | | | | | | | |
I-a | x, y+1, z | 5.2 | -15.1a -17.1b | -8.5 a -6.0 b | -21.6a -21.1b | 24.4a 33.2b | -20.8a -20.3b | O1···Cg2, N3—H3···O4, Cg4···Cg4, N3—H3···O1 |
I-b | -x+1, y+1/2, -z | 6.7 | -1.5a -1.6b | -1.1a -0.6b | -10.3 a -11.1 b | 4.7a 6.2b | -8.1a -7.9b | N1···H32a—C32, C32—H32a···Cg2 |
A···B/B···A | | | | | | | | |
I-c | x, y, z | 9.2 | -5.4a -5.1b | -2.3a -1.1 b | -7.3a -7.2b | 6.9a 7.3b | -8.1a -8.0b | O1···H5—C5, O1···S1, Cg2···S1 |
I-d | x, y-1, z | 10.0 | -1.7a -1.5b | -0.9a -0.6b | -3.6a -3.6b | 1.9a 2.7b | -4.2a -3.5b | C8—H8···N1, C7—H7···N1 |
I-e | -x+1, y-0.5, -z+1 | 10.4 | -1.2a -1.3b | -0.6a -0.3b | -5.3a -6.1b | 2.8a 3.8b | -4.3a -4.6b | C21—H21c···Cg4, C22—H22F···Cg4 |
I-f | -x+2, y-0.5, -z+1 | 12.2 | -4.6a -4.9b | -1.7a -1.2b | -8.0a -8.6b | 4.7a 7.1b | -9.6a -9.2b | C5—H5···Cg4, C6—H6···O4 |
B···B | | | | | | | | |
I-g | x, y+1, z | 5.2 | -9.9a -17.1b | -4.7a -6.0b | -19.0a -21.1b | 11.7a 33.2b | -21.9a -20.3b | N3-H3···O4, Cg4···Cg4, S1···Cg3 |
I-h | -x+2, y-0.5, -z+1 | 9.0 | -0.7a | -0.5a | -5.6a | 2.4a | -4.4a | C22—H22···H2-C2 |
II | | | | | | | | |
II-a | -x+1, -y+1, -z+2 | 7.8 | -3.9a -3.8b | -2.3a -1.1b | -14.9a -15.5b | 9.9a 11.4b | -11.2a -11.3b | C26—H26c···H7—C7, Cg1···Cg3, Cg3···Cg1,
C7—H7···H26c—C26 |
II-b | -x+1, -y+1, -z+1 | 8.4 | -0.4a -0.6b | -0.5a -0.3b | -6.5a -7.8b | 1.9a 3.0b | -5.5a -5.8b | Cg3···H32a—C32, C61—H61a···C21, C32—H32a···Cg3,
C21···H61a—C61 |
II-c | -x+1, -y+2, -z+1 | 6.2 | -8.7a -10.2b | -4.2a -4.1b | -13.3a -14.5b | 8.6a 14.4b | -17.7a -17.5b | C2—H2···O4, C26—H26a···O4, C4—H4···O4, O4···H2—C2, O4···H26a—C26,
O4···H4—C4 |
II-d | -x+2, -y+1, -z+1 | 6.9 | -7.0a -6.7b | -2.8a -2.6b | -11.8a -12.3b | 6.3a 9.2b | -15.3a -14.1b | O1···H22a—C22, C22-H22a···O1 |
II-e | -x+2, -y+2, -z+1 | 8.3 | -9.4a -10.4b | -5.0a -5.1 | -12.4a -13.4b | 10.0a 15.3b | -16.7a -16.9b | C1—H1···O1, O1···.H1—C1, C31—H31a···O1, O1···H31a—C31 |
II-f | x-1, y, z | 9.6 | -3.0a -3.1b | -1.6a -1.7b | -3.2a -3.5b | 2.0a 3.5b | -5.8a -5.4b | O1···H5—C5 |
Lattice energies of crystal structures I and II (kcal mol-1)
computed with PIXEL top | ECoul | Epol | Edisp | Erep | Etot |
I | -21.13 | -10.6 | -51.8 | 33.44 | -50.5 |
II | -17.5 | -9.1 | -43.7 | 24.4 | -45.8 |
Global and local aromaticity indices (a) HOMHED and (b) HOMA
calculated for I–X.
Values given for I and VII are averaged over two independent
molecules in the asymmetric unit. top | Cg1 | | Cg2 | | Cg3 | | Global | |
| (a) | (b) | (a) | (b) | (a) | (b) | (a) | (b) |
I | 0.74 | 0.69 | 0.78 | 0.67 | 0.99 | 0.98 | 0.83 | 0.80 |
II | 0.76 | 0.73 | 0.10 | -1.3 | 0.99 | 0.99 | 0.56 | 0.02 |
III | 0.71 | 0.66 | 0.78 | 0.64 | 1.00 | 0.99 | 0.83 | 0.76 |
IV | 0.72 | 0.68 | 0.80 | 0.67 | 1.00 | 0.99 | 0.84 | 0.77 |
V | 0.72 | 0.67 | 0.79 | 0.65 | 0.99 | 0.98 | 0.83 | 0.75 |
VI | 0.73 | 0.69 | 0.79 | 0.63 | 1.00 | 0.99 | 0.84 | 0.77 |
VII | 0.79 | 0.66 | 0.71 | 0.65 | 1.00 | 0.99 | 0.83 | 0.76 |
VIII | 0.72 | 0.67 | 0.80 | 0.55 | 1.00 | 0.99 | 0.83 | 0.72 |
IX | 0.71 | 0.66 | 0.80 | 0.57 | 0.99 | 0.98 | 0.83 | 0.75 |
X | 0.68 | 0.63 | 0.80 | 0.57 | 0.99 | 0.98 | 0.82 | 0.75 |