Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105026259/gg1264sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105026259/gg1264Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105026259/gg1264IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105026259/gg1264IIIsup4.hkl |
CCDC references: 288622; 288623; 288624
The syntheses were carried out as described previously (Tarui et al., 1996). L-Amino acids were used for the syntheses of (I), (II) and (III). Crystals of (I) and (II) were grown from aqueous hexylenglycol solutions. Crystals of (III) were grown from aqueous DMF solutions. Each peptide (8–10 mg) was dissolved in the organic solvent (0.3–0.4 ml) with heating and 1–2 drops of water (50–100 µl) were added to the solution. Crystals were grown over periods of between two weeks and a month.
H atoms of hydrated water molecules of (II) were found from the differential Fourier map by considering hydrogen bonds. These H atoms were not restrained during refinements. H atoms were treated as riding atoms, with C—H distances of 0.95–1.00 Å, N—H distances of 0.88 (CONH) or 0.91 Å (NH3), and O—H distances of 0.84 Å. In the absence of any significant anomalous scattering, the Flack (1983) parameter was meaningless (Flack & Bernardinelli, 2000). Hence, the Friedel equivalents were merged prior to the final refinements, and the absolute structure was set by reference to the known chirality of the amino acid employed. Validation check suggested pseudosymmetry for (III), but the material chirality (L-Lys) was confirmed in the structure.
For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998). Program(s) used to solve structure: SHELXD (Sheldrick, 1990b) for (I); SHELXS97 (Sheldrick, 1990a) for (II), (III). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: Mercury (Bruno et al., 2002).
C16H18N4O4 | Z = 4 |
Mr = 330.34 | F(000) = 696 |
Triclinic, P1 | Dx = 1.353 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3587 (12) Å | Cell parameters from 2719 reflections |
b = 10.3445 (13) Å | θ = 2.2–27.9° |
c = 16.925 (2) Å | µ = 0.10 mm−1 |
α = 92.079 (2)° | T = 100 K |
β = 95.775 (2)° | Plate, colourless |
γ = 95.245 (2)° | 0.25 × 0.20 × 0.04 mm |
V = 1621.7 (4) Å3 |
Bruker SMART APEX diffractometer | 6059 independent reflections |
Radiation source: MacSciences M18XCE rotating anode | 5788 reflections with I > \2s(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.366 pixels mm-1 | θmax = 25.7°, θmin = 2.0° |
ω scans | h = −9→11 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.832, Tmax = 0.998 | l = −20→16 |
8913 measured reflections |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0753P)2 + 0.9676P] where P = (Fo2 + 2Fc2)/3 |
6059 reflections | (Δ/σ)max = 0.011 |
896 parameters | Δρmax = 0.33 e Å−3 |
180 restraints | Δρmin = −0.31 e Å−3 |
C16H18N4O4 | γ = 95.245 (2)° |
Mr = 330.34 | V = 1621.7 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.3587 (12) Å | Mo Kα radiation |
b = 10.3445 (13) Å | µ = 0.10 mm−1 |
c = 16.925 (2) Å | T = 100 K |
α = 92.079 (2)° | 0.25 × 0.20 × 0.04 mm |
β = 95.775 (2)° |
Bruker SMART APEX diffractometer | 6059 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 5788 reflections with I > \2s(I) |
Tmin = 0.832, Tmax = 0.998 | Rint = 0.025 |
8913 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 180 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.33 e Å−3 |
6059 reflections | Δρmin = −0.31 e Å−3 |
896 parameters |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.0129 (. 0164) x − 2.9332 (. 0218) y + 12.9110 (. 0229) z = 5.3195 (. 0225) *. 0201 (. 0033) N1A * -.0142 (. 0032) C2A * -.0051 (. 0034) N3A *. 0182 (. 0039) C4A * -.0129 (. 0042) C5A * -.0061 (. 0037) C6A Rms deviation of fitted atoms =. 0139 5.5015 (. 0229) x + 3.7261 (. 0278) y + 10.3521 (. 0361) z = 6.8078 (. 0194) Angle to previous plane (with approximate e.s.d.) = 38.76 (. 23) *. 0008 (. 0043) C12A *. 0056 (. 0042) C13A * -.0060 (. 0044) C14A * -.0001 (. 0052) C15A *. 0066 (. 0060) C16A * -.0070 (. 0054) C17A Rms deviation of fitted atoms =. 0052 3.4151 (. 0177) x + 4.2599 (. 0189) y + 12.7715 (. 0223) z = 5.6594 (. 0040) Angle to previous plane (with approximate e.s.d.) = 14.73 (. 35) * -.0246 (. 0031) N1B *. 0347 (. 0030) C2B * -.0223 (. 0034) N3B * -.0011 (. 0037) C4B *. 0123 (. 0037) C5B *. 0010 (. 0034) C6B Rms deviation of fitted atoms =. 0202 2.4451 (. 0218) x − 5.5455 (. 0206) y + 13.6929 (. 0227) z = 5.9373 (. 0214) Angle to previous plane (with approximate e.s.d.) = 57.83 (. 15) *. 0121 (. 0038) C12B * -.0070 (. 0039) C13B * -.0015 (. 0042) C14B *. 0050 (. 0043) C15B *. 0001 (. 0045) C16B * -.0087 (. 0043) C17B Rms deviation of fitted atoms =. 0070 7.8870 (. 0111) x + 4.6700 (. 0202) y -. 3288 (. 0341) z = 4.7114 (. 0303) Angle to previous plane (with approximate e.s.d.) = 88.80 (. 17) *. 0090 (. 0033) N1C * -.0262 (. 0031) C2C *. 0240 (. 0032) N3C * -.0036 (. 0034) C4C * -.0147 (. 0039) C5C *. 0114 (. 0038) C6C Rms deviation of fitted atoms =. 0168 6.6549 (. 0188) x + 3.2685 (. 0367) y + 8.4166 (. 0439) z = 6.9808 (. 0357) Angle to previous plane (with approximate e.s.d.) = 31.19 (. 28) *. 0000 (. 0003) C12C *. 0000 (. 0003) C13C *. 0000 (. 0003) C14C *. 0000 (. 0001) C15C *. 0000 (. 0001) C16C *. 0000 (. 0001) C17C Rms deviation of fitted atoms =. 0000 8.5682 (. 0083) x − 4.7947 (. 0200) y +. 8846 (. 0349) z =. 9288 (. 0203) Angle to previous plane (with approximate e.s.d.) = 54.52 (. 19) * -.0032 (. 0033) N1D *. 0193 (. 0032) C2D * -.0200 (. 0034) N3D *. 0040 (. 0036) C4D *. 0127 (. 0041) C5D * -.0127 (. 0039) C6D Rms deviation of fitted atoms =. 0137 8.0948 (. 0120) x − 1.6207 (. 0266) y + 6.9268 (. 0388) z = 8.9597 (. 0201) Angle to previous plane (with approximate e.s.d.) = 27.75 (. 20) * -.0065 (. 0040) C12D *. 0029 (. 0041) C13D *. 0020 (. 0045) C14D * -.0032 (. 0045) C15D * -.0005 (. 0046) C16D *. 0054 (. 0046) C17D Rms deviation of fitted atoms =. 0040 —- Hydrogen bond rings (N3···O18 and N4.·O19; 8 membered ring) —- Molecules A···D[x, y + 1, z] 4.1298 (. 0418) x +. 7475 (. 0141) y + 14.1362 (. 0423) z = 7.6737 (. 0117) *. 1982 (. 0032) N3A *. 3917 (. 0045) H3A * -.2569 (. 0040) C4A * -.3639 (. 0043) N4A * -.1395 (. 0030) H4AA *. 1275 (. 0035) O18D *. 2335 (. 0040) C18D * -.1906 (. 0033) O19D Rms deviation of fitted atoms =. 2544 Molecules B···C[x + 1, y, z − 1] 6.5453 (. 0105) x + 5.0240 (. 0217) y + 6.0219 (. 0123) z = 6.5201 (. 0047) * -.1711 (. 0018) N3B *. 2112 (. 0017) H3B * -.4253 (. 0054) C4B * -.0363 (. 0024) N4B *. 3730 (. 0025) H4AB * -.0689 (. 0036) O18C *. 0894 (. 0040) C18C *. 0280 (. 0036) O19C Rms deviation of fitted atoms =. 2260 Molecules C···B 7.9675 (. 0085) x + 4.1141 (. 0197) y + 1.8349 (. 0235) z = 6.0160 (. 0134) *. 1336 (. 0021) N3C *. 0998 (. 0022) H3C *. 0549 (. 0043) C4C * -.1117 (. 0021) N4C * -.1705 (. 0021) H4AC *. 2418 (. 0034) O18B *. 0558 (. 0033) C18B * -.3037 (. 0036) O19B Rms deviation of fitted atoms =. 1681 Molecules D···A[x − 1, y − 1, z + 1] 8.2484 (. 0024) x − 4.5493 (. 0164) y + 3.9099 (. 0201) z = 3.0131 (. 0158) * -.1346 (. 0020) N3D * -.0343 (. 0022) H3D * -.1213 (. 0049) C4D *. 0789 (. 0021) N4D *. 2047 (. 0019) H4AD * -.2068 (. 0034) O18A * -.0042 (. 0040) C18A *. 2176 (. 0036) O19A Rms deviation of fitted atoms =. 1467 |
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 | Occ. (<1) | |
N1A | 1.0384 (5) | 0.8402 (4) | 0.2013 (2) | 0.0172 (9) | |
C2A | 0.9431 (5) | 0.8927 (5) | 0.2476 (3) | 0.0152 (10) | |
O2A | 0.9535 (4) | 1.0074 (3) | 0.2672 (2) | 0.0182 (8) | |
N3A | 0.8368 (4) | 0.8058 (4) | 0.2698 (2) | 0.0169 (9) | |
H3A | 0.7750 | 0.8363 | 0.2999 | 0.020* | |
C4A | 0.8184 (6) | 0.6781 (6) | 0.2497 (3) | 0.0243 (12) | |
N4A | 0.7133 (6) | 0.6065 (5) | 0.2766 (4) | 0.0415 (15) | |
H4AA | 0.6558 | 0.6421 | 0.3074 | 0.050* | |
H4BA | 0.6999 | 0.5227 | 0.2640 | 0.050* | |
C5A | 0.9161 (6) | 0.6295 (6) | 0.1983 (3) | 0.0268 (13) | |
H5A | 0.9059 | 0.5408 | 0.1802 | 0.032* | |
C6A | 1.0209 (6) | 0.7116 (5) | 0.1768 (3) | 0.0198 (11) | |
H6A | 1.0865 | 0.6800 | 0.1431 | 0.024* | |
C7A | 1.1660 (5) | 0.9264 (5) | 0.1843 (3) | 0.0170 (11) | |
H7AA | 1.2381 | 0.8729 | 0.1641 | 0.020* | |
H7BA | 1.2104 | 0.9725 | 0.2343 | 0.020* | |
C8A | 1.1266 (5) | 1.0265 (5) | 0.1230 (3) | 0.0168 (11) | |
H8AA | 1.0489 | 1.0757 | 0.1409 | 0.020* | |
H8BA | 1.2118 | 1.0889 | 0.1184 | 0.020* | |
C9A | 1.0763 (5) | 0.9587 (5) | 0.0423 (3) | 0.0169 (11) | |
O9A | 1.1247 (5) | 0.8564 (4) | 0.0233 (2) | 0.0315 (10) | |
N10A | 0.9817 (5) | 1.0149 (4) | −0.0043 (2) | 0.0161 (9) | |
H10A | 0.9523 | 1.0888 | 0.0118 | 0.019* | |
C10A | 0.9253 (5) | 0.9575 (5) | −0.0813 (3) | 0.0165 (10) | |
H10AA | 0.9443 | 0.8639 | −0.0819 | 0.020* | |
C11A | 0.7610 (6) | 0.9624 (6) | −0.0949 (4) | 0.0280 (13) | |
H11AA | 0.7400 | 1.0541 | −0.0990 | 0.034* | |
H11BA | 0.7243 | 0.9159 | −0.1461 | 0.034* | |
C12A | 0.6817 (6) | 0.9028 (6) | −0.0295 (4) | 0.0262 (13) | |
C13A | 0.7094 (6) | 0.7842 (6) | −0.0011 (3) | 0.0274 (13) | |
H13A | 0.7819 | 0.7390 | −0.0222 | 0.033* | |
C14A | 0.6341 (6) | 0.7279 (6) | 0.0580 (4) | 0.0325 (14) | |
H14A | 0.6549 | 0.6449 | 0.0757 | 0.039* | |
C15A | 0.5307 (7) | 0.7912 (7) | 0.0908 (4) | 0.0422 (17) | |
H15A | 0.4798 | 0.7535 | 0.1314 | 0.051* | |
C16A | 0.5024 (8) | 0.9103 (8) | 0.0636 (6) | 0.056 (2) | |
H16A | 0.4317 | 0.9561 | 0.0861 | 0.067* | |
C17A | 0.5758 (7) | 0.9652 (7) | 0.0035 (5) | 0.0424 (17) | |
H17A | 0.5528 | 1.0470 | −0.0151 | 0.051* | |
C18A | 0.9986 (6) | 1.0204 (5) | −0.1499 (3) | 0.0179 (11) | |
O18A | 1.0375 (4) | 1.1389 (4) | −0.1458 (2) | 0.0217 (8) | |
O19A | 1.0101 (5) | 0.9427 (4) | −0.2077 (2) | 0.0297 (10) | |
N1B | 0.3415 (4) | 0.3189 (4) | 0.2435 (2) | 0.0154 (9) | |
C2B | 0.4484 (5) | 0.3754 (5) | 0.2007 (3) | 0.0138 (10) | |
O2B | 0.4418 (4) | 0.4833 (3) | 0.1755 (2) | 0.0162 (7) | |
N3B | 0.5623 (5) | 0.3037 (4) | 0.1897 (3) | 0.0201 (10) | |
H3B | 0.6270 | 0.3328 | 0.1587 | 0.024* | |
C4B | 0.5777 (6) | 0.1910 (6) | 0.2249 (3) | 0.0242 (12) | |
N4B | 0.6936 (6) | 0.1314 (5) | 0.2131 (3) | 0.0350 (12) | |
H4AB | 0.7572 | 0.1660 | 0.1831 | 0.042* | |
H4BB | 0.7071 | 0.0573 | 0.2353 | 0.042* | |
C5B | 0.4716 (6) | 0.1388 (5) | 0.2717 (3) | 0.0214 (11) | |
H5B | 0.4815 | 0.0591 | 0.2969 | 0.026* | |
C6B | 0.3573 (6) | 0.2046 (5) | 0.2794 (3) | 0.0192 (11) | |
H6B | 0.2851 | 0.1709 | 0.3108 | 0.023* | |
C7B | 0.2157 (5) | 0.3919 (5) | 0.2538 (3) | 0.0162 (10) | |
H7AB | 0.1350 | 0.3313 | 0.2678 | 0.019* | |
H7BB | 0.1844 | 0.4301 | 0.2029 | 0.019* | |
C8B | 0.2491 (6) | 0.4994 (5) | 0.3180 (3) | 0.0194 (11) | |
H8AB | 0.1634 | 0.5482 | 0.3210 | 0.023* | |
H8BB | 0.3293 | 0.5606 | 0.3039 | 0.023* | |
C9B | 0.2911 (5) | 0.4455 (5) | 0.3991 (3) | 0.0130 (10) | |
O9B | 0.2369 (4) | 0.3391 (4) | 0.4158 (2) | 0.0188 (8) | |
N10B | 0.3856 (5) | 0.5215 (4) | 0.4480 (2) | 0.0153 (9) | |
H10B | 0.4202 | 0.5976 | 0.4329 | 0.018* | |
C10B | 0.4321 (5) | 0.4786 (5) | 0.5268 (3) | 0.0159 (10) | |
H10AB | 0.4155 | 0.3817 | 0.5262 | 0.019* | |
C11B | 0.5926 (6) | 0.5187 (5) | 0.5485 (3) | 0.0194 (11) | |
H11AB | 0.6095 | 0.6144 | 0.5463 | 0.023* | |
H11BB | 0.6189 | 0.4961 | 0.6041 | 0.023* | |
C12B | 0.6926 (6) | 0.4571 (5) | 0.4960 (3) | 0.0173 (11) | |
C13B | 0.6526 (6) | 0.3390 (5) | 0.4538 (3) | 0.0219 (11) | |
H13B | 0.5572 | 0.2986 | 0.4533 | 0.026* | |
C14B | 0.7533 (6) | 0.2794 (5) | 0.4122 (3) | 0.0237 (12) | |
H14B | 0.7263 | 0.1983 | 0.3841 | 0.028* | |
C15B | 0.8908 (7) | 0.3387 (6) | 0.4121 (4) | 0.0298 (14) | |
H15B | 0.9591 | 0.2983 | 0.3841 | 0.036* | |
C16B | 0.9295 (6) | 0.4567 (6) | 0.4526 (4) | 0.0317 (14) | |
H16B | 1.0246 | 0.4975 | 0.4523 | 0.038* | |
C17B | 0.8305 (6) | 0.5161 (6) | 0.4937 (4) | 0.0263 (12) | |
H17B | 0.8578 | 0.5982 | 0.5206 | 0.032* | |
C18B | 0.3487 (5) | 0.5365 (5) | 0.5920 (3) | 0.0139 (10) | |
O18B | 0.3147 (4) | 0.6492 (3) | 0.5882 (2) | 0.0188 (8) | |
O19B | 0.3291 (4) | 0.4620 (3) | 0.6484 (2) | 0.0222 (8) | |
N1C | 0.3184 (5) | 0.5382 (4) | 0.9240 (2) | 0.0162 (9) | |
C2C | 0.3397 (5) | 0.4894 (5) | 0.8497 (3) | 0.0130 (10) | |
O2C | 0.3885 (4) | 0.3859 (3) | 0.8393 (2) | 0.0188 (8) | |
N3C | 0.2989 (5) | 0.5647 (4) | 0.7876 (2) | 0.0143 (8) | |
H3C | 0.3184 | 0.5400 | 0.7398 | 0.017* | |
C4C | 0.2312 (5) | 0.6736 (5) | 0.7944 (3) | 0.0157 (10) | |
N4C | 0.1935 (5) | 0.7348 (4) | 0.7302 (3) | 0.0211 (10) | |
H4AC | 0.2124 | 0.7047 | 0.6834 | 0.025* | |
H4BC | 0.1493 | 0.8059 | 0.7338 | 0.025* | |
C5C | 0.2072 (7) | 0.7172 (6) | 0.8716 (3) | 0.0253 (12) | |
H5C | 0.1593 | 0.7930 | 0.8792 | 0.030* | |
C6C | 0.2528 (6) | 0.6500 (5) | 0.9336 (3) | 0.0191 (11) | |
H6C | 0.2395 | 0.6806 | 0.9857 | 0.023* | |
C7C | 0.3619 (5) | 0.4616 (5) | 0.9936 (3) | 0.0168 (11) | |
H7AC | 0.3729 | 0.5186 | 1.0425 | 0.020* | |
H7BC | 0.4563 | 0.4287 | 0.9872 | 0.020* | |
C8C | 0.2511 (5) | 0.3484 (5) | 1.0018 (3) | 0.0152 (10) | |
H8AC | 0.2844 | 0.2974 | 1.0473 | 0.018* | |
H8BC | 0.2410 | 0.2909 | 0.9532 | 0.018* | |
C9C | 0.1058 (5) | 0.3947 (4) | 1.0147 (3) | 0.0121 (10) | |
O9C | 0.0954 (4) | 0.4761 (4) | 1.0693 (2) | 0.0184 (8) | |
N10C | −0.0053 (4) | 0.3480 (4) | 0.9647 (2) | 0.0143 (9) | |
H10C | 0.0062 | 0.2932 | 0.9254 | 0.017* | |
C10C | −0.1470 (5) | 0.3881 (5) | 0.9751 (3) | 0.0159 (10) | |
H10AC | −0.1374 | 0.4846 | 0.9845 | 0.019* | |
C11C | −0.2514 (5) | 0.3537 (5) | 0.8995 (3) | 0.0186 (11) | |
H11AC | −0.2458 | 0.2617 | 0.8828 | 0.022* | |
H11BC | −0.3512 | 0.3629 | 0.9118 | 0.022* | |
C12C | −0.2186 (5) | 0.4380 (4) | 0.8322 (2) | 0.0169 (12) | 0.96 (3) |
C13C | −0.1294 (5) | 0.3994 (5) | 0.7766 (3) | 0.0330 (16) | 0.96 (3) |
H13AC | −0.0925 | 0.3170 | 0.7795 | 0.040* | 0.96 (3) |
C14C | −0.0941 (8) | 0.4815 (6) | 0.7168 (3) | 0.046 (2) | 0.96 (3) |
H14AC | −0.0331 | 0.4552 | 0.6788 | 0.056* | 0.96 (3) |
C15C | −0.1480 (11) | 0.6022 (5) | 0.7126 (3) | 0.052 (3) | 0.96 (3) |
H15AC | −0.1239 | 0.6583 | 0.6718 | 0.062* | 0.96 (3) |
C16C | −0.2372 (11) | 0.6407 (4) | 0.7682 (3) | 0.053 (3) | 0.96 (3) |
H16AC | −0.2741 | 0.7232 | 0.7653 | 0.063* | 0.96 (3) |
C17C | −0.2725 (8) | 0.5586 (4) | 0.8279 (3) | 0.0395 (19) | 0.96 (3) |
H17AC | −0.3335 | 0.5850 | 0.8659 | 0.047* | 0.96 (3) |
C12'C | −0.238 (9) | 0.438 (5) | 0.830 (3) | 0.034 (12) | 0.04 (3) |
C13'C | −0.152 (13) | 0.406 (11) | 0.771 (4) | 0.032 (11) | 0.04 (3) |
H13'C | −0.0997 | 0.3315 | 0.7758 | 0.038* | 0.04 (3) |
C14'C | −0.14 (2) | 0.483 (14) | 0.706 (6) | 0.039 (12) | 0.04 (3) |
H14'C | −0.0825 | 0.4610 | 0.6660 | 0.046* | 0.04 (3) |
C15'C | −0.22 (2) | 0.592 (13) | 0.700 (6) | 0.052 (13) | 0.04 (3) |
H15'C | −0.2105 | 0.6447 | 0.6550 | 0.063* | 0.04 (3) |
C16'C | −0.30 (2) | 0.624 (11) | 0.758 (7) | 0.047 (13) | 0.04 (3) |
H16'C | −0.3557 | 0.6987 | 0.7536 | 0.057* | 0.04 (3) |
C17'C | −0.314 (16) | 0.547 (8) | 0.823 (5) | 0.037 (12) | 0.04 (3) |
H17'C | −0.3729 | 0.5692 | 0.8634 | 0.045* | 0.04 (3) |
C18C | −0.2051 (6) | 0.3269 (5) | 1.0478 (3) | 0.0181 (11) | |
O18C | −0.3036 (4) | 0.3912 (4) | 1.0749 (2) | 0.0225 (8) | |
O19C | −0.1637 (4) | 0.2280 (4) | 1.0751 (2) | 0.0218 (8) | |
N1D | 0.0463 (4) | −0.0146 (4) | 0.5187 (2) | 0.0141 (9) | |
C2D | 0.0184 (5) | −0.0554 (4) | 0.5932 (3) | 0.0111 (9) | |
O2D | −0.0335 (4) | −0.1638 (3) | 0.6022 (2) | 0.0189 (8) | |
N3D | 0.0577 (5) | 0.0344 (4) | 0.6544 (2) | 0.0150 (9) | |
H3D | 0.0356 | 0.0130 | 0.7019 | 0.018* | |
C4D | 0.1274 (6) | 0.1528 (5) | 0.6486 (3) | 0.0193 (11) | |
N4D | 0.1630 (5) | 0.2280 (5) | 0.7123 (3) | 0.0267 (11) | |
H4AD | 0.1415 | 0.2013 | 0.7588 | 0.032* | |
H4BD | 0.2086 | 0.3055 | 0.7088 | 0.032* | |
C5D | 0.1572 (7) | 0.1899 (5) | 0.5711 (4) | 0.0277 (13) | |
H5D | 0.2067 | 0.2720 | 0.5634 | 0.033* | |
C6D | 0.1138 (6) | 0.1064 (5) | 0.5098 (3) | 0.0219 (12) | |
H6D | 0.1304 | 0.1318 | 0.4579 | 0.026* | |
C7D | 0.0088 (5) | −0.1060 (5) | 0.4507 (3) | 0.0155 (10) | |
H7AD | −0.0015 | −0.0572 | 0.4015 | 0.019* | |
H7BD | −0.0853 | −0.1551 | 0.4561 | 0.019* | |
C8D | 0.1234 (5) | −0.2016 (5) | 0.4437 (3) | 0.0135 (10) | |
H8AD | 0.1375 | −0.2480 | 0.4936 | 0.016* | |
H8BD | 0.0907 | −0.2668 | 0.3998 | 0.016* | |
C9D | 0.2650 (5) | −0.1283 (5) | 0.4276 (3) | 0.0148 (10) | |
O9D | 0.2714 (4) | −0.0574 (4) | 0.3716 (2) | 0.0228 (8) | |
N10D | 0.3801 (4) | −0.1442 (4) | 0.4784 (2) | 0.0135 (8) | |
H10D | 0.3714 | −0.1933 | 0.5193 | 0.016* | |
C10D | 0.5187 (5) | −0.0803 (5) | 0.4656 (3) | 0.0171 (11) | |
H10AD | 0.5058 | 0.0112 | 0.4513 | 0.020* | |
C11D | 0.6272 (6) | −0.0772 (6) | 0.5404 (3) | 0.0209 (11) | |
H11AD | 0.6422 | −0.1676 | 0.5539 | 0.025* | |
H11BD | 0.7209 | −0.0343 | 0.5282 | 0.025* | |
C12D | 0.5809 (5) | −0.0073 (5) | 0.6120 (3) | 0.0192 (11) | |
C13D | 0.5184 (6) | −0.0759 (6) | 0.6703 (4) | 0.0270 (13) | |
H13D | 0.5050 | −0.1681 | 0.6654 | 0.032* | |
C14D | 0.4752 (7) | −0.0114 (7) | 0.7358 (4) | 0.0344 (15) | |
H14D | 0.4321 | −0.0599 | 0.7753 | 0.041* | |
C15D | 0.4938 (7) | 0.1205 (7) | 0.7442 (4) | 0.0387 (16) | |
H15D | 0.4633 | 0.1639 | 0.7891 | 0.046* | |
C16D | 0.5567 (8) | 0.1905 (6) | 0.6874 (4) | 0.0427 (18) | |
H16D | 0.5702 | 0.2826 | 0.6929 | 0.051* | |
C17D | 0.6004 (8) | 0.1264 (6) | 0.6221 (4) | 0.0377 (16) | |
H17D | 0.6450 | 0.1756 | 0.5834 | 0.045* | |
C18D | 0.5841 (5) | −0.1494 (5) | 0.3966 (3) | 0.0159 (10) | |
O18D | 0.6704 (4) | −0.0788 (4) | 0.3602 (2) | 0.0210 (8) | |
O19D | 0.5520 (4) | −0.2677 (4) | 0.3822 (2) | 0.0240 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.018 (2) | 0.024 (2) | 0.010 (2) | 0.0037 (18) | 0.0038 (17) | −0.0016 (17) |
C2A | 0.015 (2) | 0.023 (3) | 0.008 (2) | 0.001 (2) | 0.0017 (19) | 0.003 (2) |
O2A | 0.0228 (19) | 0.019 (2) | 0.0139 (18) | 0.0030 (15) | 0.0061 (15) | 0.0008 (14) |
N3A | 0.012 (2) | 0.027 (2) | 0.012 (2) | 0.0014 (17) | 0.0039 (16) | −0.0032 (18) |
C4A | 0.019 (3) | 0.030 (3) | 0.023 (3) | −0.003 (2) | 0.005 (2) | −0.011 (2) |
N4A | 0.036 (3) | 0.026 (3) | 0.061 (4) | −0.016 (2) | 0.027 (3) | −0.022 (3) |
C5A | 0.033 (3) | 0.020 (3) | 0.026 (3) | −0.003 (2) | 0.006 (2) | −0.018 (2) |
C6A | 0.019 (3) | 0.025 (3) | 0.014 (2) | 0.002 (2) | −0.001 (2) | −0.010 (2) |
C7A | 0.018 (3) | 0.023 (3) | 0.010 (2) | 0.002 (2) | 0.0024 (19) | −0.001 (2) |
C8A | 0.016 (2) | 0.024 (3) | 0.011 (2) | 0.002 (2) | 0.006 (2) | 0.002 (2) |
C9A | 0.017 (3) | 0.024 (3) | 0.012 (2) | 0.003 (2) | 0.010 (2) | 0.002 (2) |
O9A | 0.043 (3) | 0.039 (2) | 0.016 (2) | 0.029 (2) | −0.0041 (18) | −0.0064 (17) |
N10A | 0.021 (2) | 0.017 (2) | 0.013 (2) | 0.0079 (17) | 0.0057 (17) | −0.0019 (16) |
C10A | 0.021 (3) | 0.014 (2) | 0.014 (3) | 0.003 (2) | 0.001 (2) | −0.0031 (19) |
C11A | 0.024 (3) | 0.029 (3) | 0.030 (3) | 0.006 (2) | −0.007 (2) | 0.004 (2) |
C12A | 0.016 (3) | 0.030 (3) | 0.031 (3) | 0.002 (2) | −0.003 (2) | −0.009 (2) |
C13A | 0.028 (3) | 0.029 (3) | 0.025 (3) | 0.003 (2) | 0.003 (2) | −0.005 (2) |
C14A | 0.025 (3) | 0.033 (3) | 0.037 (4) | −0.007 (3) | 0.001 (3) | 0.002 (3) |
C15A | 0.027 (3) | 0.048 (4) | 0.051 (4) | −0.011 (3) | 0.015 (3) | 0.009 (3) |
C16A | 0.041 (4) | 0.049 (5) | 0.085 (6) | 0.006 (3) | 0.040 (4) | 0.002 (4) |
C17A | 0.033 (4) | 0.031 (4) | 0.065 (5) | 0.011 (3) | 0.012 (3) | 0.003 (3) |
C18A | 0.025 (3) | 0.020 (3) | 0.009 (2) | 0.011 (2) | −0.002 (2) | −0.003 (2) |
O18A | 0.030 (2) | 0.024 (2) | 0.0121 (18) | 0.0036 (16) | 0.0068 (16) | −0.0050 (15) |
O19A | 0.059 (3) | 0.019 (2) | 0.0132 (19) | 0.0099 (19) | 0.0095 (18) | −0.0009 (15) |
N1B | 0.016 (2) | 0.022 (2) | 0.0071 (19) | 0.0002 (17) | −0.0029 (16) | −0.0032 (16) |
C2B | 0.013 (2) | 0.023 (3) | 0.005 (2) | −0.0026 (19) | −0.0002 (18) | −0.0036 (19) |
O2B | 0.0204 (18) | 0.0188 (18) | 0.0104 (17) | 0.0021 (14) | 0.0055 (14) | 0.0025 (14) |
N3B | 0.020 (2) | 0.028 (2) | 0.015 (2) | 0.0044 (19) | 0.0102 (18) | 0.0053 (18) |
C4B | 0.024 (3) | 0.027 (3) | 0.022 (3) | 0.008 (2) | −0.001 (2) | 0.000 (2) |
N4B | 0.042 (3) | 0.034 (3) | 0.034 (3) | 0.020 (2) | 0.010 (2) | 0.012 (2) |
C5B | 0.036 (3) | 0.013 (2) | 0.017 (3) | 0.006 (2) | 0.003 (2) | 0.005 (2) |
C6B | 0.028 (3) | 0.018 (3) | 0.011 (2) | 0.000 (2) | 0.002 (2) | −0.0022 (19) |
C7B | 0.011 (2) | 0.030 (3) | 0.007 (2) | 0.000 (2) | 0.0024 (18) | 0.002 (2) |
C8B | 0.017 (3) | 0.030 (3) | 0.013 (3) | 0.008 (2) | 0.004 (2) | 0.005 (2) |
C9B | 0.015 (2) | 0.015 (3) | 0.010 (2) | 0.0026 (19) | 0.0073 (19) | −0.0017 (19) |
O9B | 0.0190 (18) | 0.025 (2) | 0.0107 (17) | −0.0058 (15) | 0.0028 (14) | 0.0010 (14) |
N10B | 0.020 (2) | 0.017 (2) | 0.009 (2) | −0.0011 (17) | 0.0053 (17) | 0.0009 (16) |
C10B | 0.019 (3) | 0.024 (3) | 0.005 (2) | 0.000 (2) | 0.0000 (19) | 0.0037 (19) |
C11B | 0.022 (3) | 0.019 (3) | 0.016 (3) | −0.002 (2) | 0.001 (2) | −0.002 (2) |
C12B | 0.019 (3) | 0.024 (3) | 0.010 (2) | 0.002 (2) | 0.003 (2) | 0.005 (2) |
C13B | 0.020 (3) | 0.025 (3) | 0.020 (3) | −0.001 (2) | 0.005 (2) | −0.002 (2) |
C14B | 0.024 (3) | 0.024 (3) | 0.023 (3) | 0.001 (2) | 0.002 (2) | −0.009 (2) |
C15B | 0.034 (3) | 0.033 (3) | 0.025 (3) | 0.010 (3) | 0.009 (3) | −0.001 (3) |
C16B | 0.016 (3) | 0.037 (4) | 0.044 (4) | −0.001 (2) | 0.011 (3) | 0.006 (3) |
C17B | 0.031 (3) | 0.022 (3) | 0.026 (3) | −0.001 (2) | 0.009 (2) | −0.002 (2) |
C18B | 0.014 (2) | 0.020 (3) | 0.007 (2) | −0.002 (2) | −0.0004 (18) | −0.0023 (19) |
O18B | 0.024 (2) | 0.023 (2) | 0.0106 (17) | 0.0048 (15) | 0.0063 (14) | 0.0033 (14) |
O19B | 0.040 (2) | 0.0153 (18) | 0.0113 (18) | −0.0016 (16) | 0.0093 (16) | −0.0012 (14) |
N1C | 0.021 (2) | 0.019 (2) | 0.009 (2) | 0.0033 (17) | 0.0020 (17) | 0.0009 (17) |
C2C | 0.011 (2) | 0.018 (3) | 0.011 (2) | 0.0016 (19) | 0.0036 (19) | −0.0027 (19) |
O2C | 0.025 (2) | 0.0187 (19) | 0.0141 (18) | 0.0070 (15) | 0.0067 (15) | −0.0010 (15) |
N3C | 0.020 (2) | 0.017 (2) | 0.0064 (19) | 0.0032 (17) | 0.0044 (16) | 0.0023 (15) |
C4C | 0.019 (2) | 0.016 (2) | 0.013 (2) | 0.004 (2) | 0.009 (2) | 0.0013 (19) |
N4C | 0.028 (2) | 0.023 (2) | 0.016 (2) | 0.010 (2) | 0.0097 (19) | 0.0083 (19) |
C5C | 0.040 (3) | 0.023 (3) | 0.016 (3) | 0.009 (2) | 0.014 (2) | 0.002 (2) |
C6C | 0.026 (3) | 0.021 (3) | 0.012 (2) | 0.005 (2) | 0.009 (2) | −0.004 (2) |
C7C | 0.015 (2) | 0.029 (3) | 0.007 (2) | 0.010 (2) | 0.0008 (19) | 0.000 (2) |
C8C | 0.018 (3) | 0.013 (2) | 0.016 (2) | 0.0053 (19) | 0.003 (2) | 0.0045 (19) |
C9C | 0.015 (2) | 0.011 (2) | 0.011 (2) | 0.0006 (18) | 0.0022 (19) | 0.0056 (18) |
O9C | 0.0208 (19) | 0.025 (2) | 0.0089 (17) | 0.0024 (15) | 0.0019 (14) | −0.0037 (14) |
N10C | 0.015 (2) | 0.018 (2) | 0.0096 (19) | 0.0002 (17) | 0.0039 (16) | −0.0052 (16) |
C10C | 0.014 (2) | 0.018 (3) | 0.017 (3) | 0.004 (2) | 0.005 (2) | 0.000 (2) |
C11C | 0.013 (2) | 0.028 (3) | 0.014 (2) | 0.003 (2) | 0.000 (2) | −0.003 (2) |
C12C | 0.014 (3) | 0.023 (3) | 0.012 (3) | −0.005 (2) | −0.002 (2) | 0.000 (2) |
C13C | 0.019 (3) | 0.055 (4) | 0.025 (3) | 0.002 (3) | 0.002 (3) | 0.014 (3) |
C14C | 0.027 (4) | 0.082 (6) | 0.028 (4) | −0.008 (4) | −0.002 (3) | 0.023 (4) |
C15C | 0.050 (6) | 0.064 (5) | 0.029 (4) | −0.042 (4) | −0.023 (4) | 0.034 (4) |
C16C | 0.089 (8) | 0.026 (4) | 0.034 (4) | −0.010 (4) | −0.033 (5) | 0.010 (3) |
C17C | 0.052 (5) | 0.034 (4) | 0.027 (4) | 0.000 (3) | −0.012 (3) | −0.003 (3) |
C12'C | 0.03 (2) | 0.04 (2) | 0.02 (2) | 0.00 (2) | 0.001 (19) | 0.00 (2) |
C13'C | 0.017 (19) | 0.05 (2) | 0.021 (19) | −0.002 (19) | −0.007 (19) | 0.011 (19) |
C14'C | 0.03 (2) | 0.06 (2) | 0.025 (19) | −0.02 (2) | 0.000 (19) | 0.024 (19) |
C15'C | 0.06 (2) | 0.05 (2) | 0.03 (2) | −0.02 (2) | −0.01 (2) | 0.01 (2) |
C16'C | 0.06 (2) | 0.04 (2) | 0.03 (2) | −0.02 (2) | −0.02 (2) | 0.01 (2) |
C17'C | 0.05 (2) | 0.03 (2) | 0.02 (2) | −0.008 (19) | −0.012 (19) | 0.006 (19) |
C18C | 0.017 (3) | 0.024 (3) | 0.014 (2) | 0.006 (2) | 0.003 (2) | −0.003 (2) |
O18C | 0.023 (2) | 0.030 (2) | 0.0193 (19) | 0.0126 (16) | 0.0131 (16) | 0.0049 (16) |
O19C | 0.026 (2) | 0.024 (2) | 0.0185 (19) | 0.0093 (16) | 0.0102 (16) | 0.0057 (16) |
N1D | 0.012 (2) | 0.022 (2) | 0.010 (2) | 0.0062 (17) | 0.0073 (16) | 0.0007 (16) |
C2D | 0.014 (2) | 0.010 (2) | 0.010 (2) | −0.0020 (18) | 0.0038 (18) | 0.0060 (18) |
O2D | 0.0234 (19) | 0.0184 (19) | 0.0152 (18) | −0.0030 (15) | 0.0088 (15) | 0.0002 (14) |
N3D | 0.016 (2) | 0.021 (2) | 0.008 (2) | 0.0014 (17) | 0.0048 (16) | −0.0006 (16) |
C4D | 0.018 (3) | 0.022 (3) | 0.020 (3) | 0.004 (2) | 0.008 (2) | −0.006 (2) |
N4D | 0.028 (3) | 0.023 (2) | 0.029 (3) | −0.002 (2) | 0.012 (2) | −0.009 (2) |
C5D | 0.034 (3) | 0.016 (3) | 0.035 (3) | −0.006 (2) | 0.024 (3) | 0.001 (2) |
C6D | 0.029 (3) | 0.019 (3) | 0.021 (3) | 0.004 (2) | 0.017 (2) | 0.005 (2) |
C7D | 0.012 (2) | 0.029 (3) | 0.006 (2) | 0.002 (2) | 0.0029 (18) | 0.000 (2) |
C8D | 0.011 (2) | 0.019 (3) | 0.011 (2) | 0.0021 (19) | 0.0063 (19) | −0.0022 (19) |
C9D | 0.019 (3) | 0.016 (2) | 0.011 (2) | 0.004 (2) | 0.007 (2) | −0.0041 (19) |
O9D | 0.022 (2) | 0.032 (2) | 0.0145 (18) | 0.0004 (16) | 0.0035 (15) | 0.0088 (16) |
N10D | 0.014 (2) | 0.022 (2) | 0.0049 (19) | 0.0027 (17) | 0.0022 (16) | 0.0043 (16) |
C10D | 0.012 (2) | 0.023 (3) | 0.017 (3) | 0.001 (2) | 0.005 (2) | 0.006 (2) |
C11D | 0.014 (3) | 0.028 (3) | 0.021 (3) | 0.004 (2) | 0.001 (2) | 0.000 (2) |
C12D | 0.008 (2) | 0.025 (3) | 0.024 (3) | 0.001 (2) | −0.003 (2) | −0.003 (2) |
C13D | 0.026 (3) | 0.028 (3) | 0.026 (3) | −0.002 (2) | 0.006 (2) | −0.009 (2) |
C14D | 0.030 (3) | 0.043 (4) | 0.031 (3) | 0.002 (3) | 0.008 (3) | −0.005 (3) |
C15D | 0.028 (3) | 0.055 (4) | 0.031 (3) | 0.014 (3) | −0.009 (3) | −0.018 (3) |
C16D | 0.057 (4) | 0.025 (3) | 0.042 (4) | 0.015 (3) | −0.017 (3) | −0.015 (3) |
C17D | 0.055 (4) | 0.029 (3) | 0.027 (3) | −0.001 (3) | −0.005 (3) | 0.002 (3) |
C18D | 0.008 (2) | 0.023 (3) | 0.017 (3) | 0.006 (2) | 0.0000 (19) | 0.004 (2) |
O18D | 0.0168 (18) | 0.0207 (19) | 0.027 (2) | 0.0010 (15) | 0.0124 (16) | 0.0019 (16) |
O19D | 0.029 (2) | 0.020 (2) | 0.024 (2) | −0.0048 (16) | 0.0150 (17) | −0.0009 (16) |
N1A—C6A | 1.369 (7) | N3C—H3C | 0.8800 |
N1A—C2A | 1.380 (7) | C4C—N4C | 1.312 (7) |
N1A—C7A | 1.481 (7) | C4C—C5C | 1.412 (7) |
C2A—O2A | 1.213 (6) | N4C—H4AC | 0.8800 |
C2A—N3A | 1.370 (6) | N4C—H4BC | 0.8800 |
N3A—C4A | 1.343 (7) | C5C—C6C | 1.335 (8) |
N3A—H3A | 0.8800 | C5C—H5C | 0.9500 |
C4A—N4A | 1.306 (8) | C6C—H6C | 0.9500 |
C4A—C5A | 1.434 (8) | C7C—C8C | 1.512 (7) |
N4A—H4AA | 0.8800 | C7C—H7AC | 0.9900 |
N4A—H4BA | 0.8800 | C7C—H7BC | 0.9900 |
C5A—C6A | 1.327 (8) | C8C—C9C | 1.515 (7) |
C5A—H5A | 0.9500 | C8C—H8AC | 0.9900 |
C6A—H6A | 0.9500 | C8C—H8BC | 0.9900 |
C7A—C8A | 1.535 (7) | C9C—O9C | 1.245 (6) |
C7A—H7AA | 0.9900 | C9C—N10C | 1.316 (6) |
C7A—H7BA | 0.9900 | N10C—C10C | 1.450 (6) |
C8A—C9A | 1.523 (7) | N10C—H10C | 0.8800 |
C8A—H8AA | 0.9900 | C10C—C18C | 1.529 (7) |
C8A—H8BA | 0.9900 | C10C—C11C | 1.539 (7) |
C9A—O9A | 1.233 (6) | C10C—H10AC | 1.0000 |
C9A—N10A | 1.316 (7) | C11C—C12C | 1.500 (6) |
N10A—C10A | 1.441 (6) | C11C—C12'C | 1.50 |
N10A—H10A | 0.8800 | C11C—H11AC | 0.9900 |
C10A—C11A | 1.537 (8) | C11C—H11BC | 0.9900 |
C10A—C18A | 1.541 (7) | C12C—C13C | 1.3900 |
C10A—H10AA | 1.0000 | C12C—C17C | 1.3900 |
C11A—C12A | 1.512 (9) | C13C—C14C | 1.3900 |
C11A—H11AA | 0.9900 | C13C—H13AC | 0.9500 |
C11A—H11BA | 0.9900 | C14C—C15C | 1.3900 |
C12A—C13A | 1.371 (9) | C14C—H14AC | 0.9500 |
C12A—C17A | 1.383 (9) | C15C—C16C | 1.3900 |
C13A—C14A | 1.394 (9) | C15C—H15AC | 0.9500 |
C13A—H13A | 0.9500 | C16C—C17C | 1.3900 |
C14A—C15A | 1.367 (10) | C16C—H16AC | 0.9500 |
C14A—H14A | 0.9500 | C17C—H17AC | 0.9500 |
C15A—C16A | 1.369 (11) | C12'C—C13'C | 1.39 |
C15A—H15A | 0.9500 | C12'C—C17'C | 1.39 |
C16A—C17A | 1.393 (11) | C13'C—C14'C | 1.39 |
C16A—H16A | 0.9500 | C13'C—H13'C | 0.95 |
C17A—H17A | 0.9500 | C14'C—C15'C | 1.41 |
C18A—O18A | 1.244 (6) | C14'C—H14'C | 0.95 |
C18A—O19A | 1.264 (6) | C15'C—C16'C | 1.34 |
N1B—C6B | 1.361 (7) | C15'C—H15'C | 0.95 |
N1B—C2B | 1.392 (6) | C16'C—C17'C | 1.39 |
N1B—C7B | 1.477 (7) | C16'C—H16'C | 0.97 |
C2B—O2B | 1.214 (6) | C17'C—H17'C | 0.95 |
C2B—N3B | 1.377 (7) | C18C—O19C | 1.217 (6) |
N3B—C4B | 1.340 (7) | C18C—O18C | 1.295 (6) |
N3B—H3B | 0.8800 | N1D—C6D | 1.370 (7) |
C4B—N4B | 1.325 (8) | N1D—C2D | 1.386 (6) |
C4B—C5B | 1.413 (8) | N1D—C7D | 1.455 (6) |
N4B—H4AB | 0.8800 | C2D—O2D | 1.202 (6) |
N4B—H4BB | 0.8800 | C2D—N3D | 1.365 (6) |
C5B—C6B | 1.335 (8) | N3D—C4D | 1.346 (7) |
C5B—H5B | 0.9500 | N3D—H3D | 0.8800 |
C6B—H6B | 0.9500 | C4D—N4D | 1.302 (7) |
C7B—C8B | 1.514 (7) | C4D—C5D | 1.427 (8) |
C7B—H7AB | 0.9900 | N4D—H4AD | 0.8800 |
C7B—H7BB | 0.9900 | N4D—H4BD | 0.8800 |
C8B—C9B | 1.529 (7) | C5D—C6D | 1.331 (8) |
C8B—H8AB | 0.9900 | C5D—H5D | 0.9500 |
C8B—H8BB | 0.9900 | C6D—H6D | 0.9500 |
C9B—O9B | 1.224 (6) | C7D—C8D | 1.535 (7) |
C9B—N10B | 1.328 (6) | C7D—H7AD | 0.9900 |
N10B—C10B | 1.458 (6) | C7D—H7BD | 0.9900 |
N10B—H10B | 0.8800 | C8D—C9D | 1.520 (7) |
C10B—C11B | 1.526 (7) | C8D—H8AD | 0.9900 |
C10B—C18B | 1.549 (7) | C8D—H8BD | 0.9900 |
C10B—H10AB | 1.0000 | C9D—O9D | 1.222 (6) |
C11B—C12B | 1.519 (7) | C9D—N10D | 1.336 (6) |
C11B—H11AB | 0.9900 | N10D—C10D | 1.442 (6) |
C11B—H11BB | 0.9900 | N10D—H10D | 0.8800 |
C12B—C17B | 1.381 (8) | C10D—C11D | 1.539 (7) |
C12B—C13B | 1.394 (8) | C10D—C18D | 1.552 (7) |
C13B—C14B | 1.404 (8) | C10D—H10AD | 1.0000 |
C13B—H13B | 0.9500 | C11D—C12D | 1.510 (8) |
C14B—C15B | 1.374 (9) | C11D—H11AD | 0.9900 |
C14B—H14B | 0.9500 | C11D—H11BD | 0.9900 |
C15B—C16B | 1.378 (9) | C12D—C17D | 1.381 (8) |
C15B—H15B | 0.9500 | C12D—C13D | 1.382 (8) |
C16B—C17B | 1.387 (8) | C13D—C14D | 1.388 (8) |
C16B—H16B | 0.9500 | C13D—H13D | 0.9500 |
C17B—H17B | 0.9500 | C14D—C15D | 1.360 (10) |
C18B—O18B | 1.238 (6) | C14D—H14D | 0.9500 |
C18B—O19B | 1.265 (6) | C15D—C16D | 1.372 (11) |
N1C—C6C | 1.370 (7) | C15D—H15D | 0.9500 |
N1C—C2C | 1.377 (6) | C16D—C17D | 1.384 (10) |
N1C—C7C | 1.487 (6) | C16D—H16D | 0.9500 |
C2C—O2C | 1.216 (6) | C17D—H17D | 0.9500 |
C2C—N3C | 1.375 (6) | C18D—O19D | 1.242 (6) |
N3C—C4C | 1.349 (6) | C18D—O18D | 1.262 (6) |
C6A—N1A—C2A | 121.2 (4) | N3C—C4C—C5C | 117.5 (5) |
C6A—N1A—C7A | 121.5 (4) | C4C—N4C—H4AC | 120.0 |
C2A—N1A—C7A | 117.1 (4) | C4C—N4C—H4BC | 120.0 |
O2A—C2A—N3A | 122.8 (5) | H4AC—N4C—H4BC | 120.0 |
O2A—C2A—N1A | 122.2 (5) | C6C—C5C—C4C | 119.0 (5) |
N3A—C2A—N1A | 115.0 (4) | C6C—C5C—H5C | 120.5 |
C4A—N3A—C2A | 125.8 (5) | C4C—C5C—H5C | 120.5 |
C4A—N3A—H3A | 117.1 | C5C—C6C—N1C | 121.7 (5) |
C2A—N3A—H3A | 117.1 | C5C—C6C—H6C | 119.2 |
N4A—C4A—N3A | 118.9 (5) | N1C—C6C—H6C | 119.2 |
N4A—C4A—C5A | 124.1 (5) | N1C—C7C—C8C | 111.1 (4) |
N3A—C4A—C5A | 117.0 (5) | N1C—C7C—H7AC | 109.4 |
C4A—N4A—H4AA | 120.0 | C8C—C7C—H7AC | 109.4 |
C4A—N4A—H4BA | 120.0 | N1C—C7C—H7BC | 109.4 |
H4AA—N4A—H4BA | 120.0 | C8C—C7C—H7BC | 109.4 |
C6A—C5A—C4A | 118.2 (5) | H7AC—C7C—H7BC | 108.0 |
C6A—C5A—H5A | 120.9 | C7C—C8C—C9C | 111.2 (4) |
C4A—C5A—H5A | 120.9 | C7C—C8C—H8AC | 109.4 |
C5A—C6A—N1A | 122.6 (5) | C9C—C8C—H8AC | 109.4 |
C5A—C6A—H6A | 118.7 | C7C—C8C—H8BC | 109.4 |
N1A—C6A—H6A | 118.7 | C9C—C8C—H8BC | 109.4 |
N1A—C7A—C8A | 112.1 (4) | H8AC—C8C—H8BC | 108.0 |
N1A—C7A—H7AA | 109.2 | O9C—C9C—N10C | 122.5 (5) |
C8A—C7A—H7AA | 109.2 | O9C—C9C—C8C | 120.3 (4) |
N1A—C7A—H7BA | 109.2 | N10C—C9C—C8C | 117.1 (4) |
C8A—C7A—H7BA | 109.2 | C9C—N10C—C10C | 119.2 (4) |
H7AA—C7A—H7BA | 107.9 | C9C—N10C—H10C | 120.4 |
C9A—C8A—C7A | 110.3 (4) | C10C—N10C—H10C | 120.4 |
C9A—C8A—H8AA | 109.6 | N10C—C10C—C18C | 110.6 (4) |
C7A—C8A—H8AA | 109.6 | N10C—C10C—C11C | 110.6 (4) |
C9A—C8A—H8BA | 109.6 | C18C—C10C—C11C | 111.3 (4) |
C7A—C8A—H8BA | 109.6 | N10C—C10C—H10AC | 108.1 |
H8AA—C8A—H8BA | 108.1 | C18C—C10C—H10AC | 108.1 |
O9A—C9A—N10A | 123.2 (5) | C11C—C10C—H10AC | 108.1 |
O9A—C9A—C8A | 119.9 (5) | C12C—C11C—C10C | 112.7 (4) |
N10A—C9A—C8A | 116.9 (4) | C12'C—C11C—C10C | 118 (3) |
C9A—N10A—C10A | 121.2 (4) | C12C—C11C—H11AC | 109.1 |
C9A—N10A—H10A | 119.4 | C12'C—C11C—H11AC | 110.0 |
C10A—N10A—H10A | 119.4 | C10C—C11C—H11AC | 109.1 |
N10A—C10A—C11A | 110.7 (4) | C12C—C11C—H11BC | 109.1 |
N10A—C10A—C18A | 112.9 (4) | C12'C—C11C—H11BC | 102.5 |
C11A—C10A—C18A | 110.3 (4) | C10C—C11C—H11BC | 109.1 |
N10A—C10A—H10AA | 107.5 | H11AC—C11C—H11BC | 107.8 |
C11A—C10A—H10AA | 107.5 | C13C—C12C—C17C | 120.0 |
C18A—C10A—H10AA | 107.5 | C13C—C12C—C11C | 120.7 (3) |
C12A—C11A—C10A | 113.3 (5) | C17C—C12C—C11C | 119.2 (3) |
C12A—C11A—H11AA | 108.9 | C12C—C13C—C14C | 120.0 |
C10A—C11A—H11AA | 108.9 | C12C—C13C—H13AC | 120.0 |
C12A—C11A—H11BA | 108.9 | C14C—C13C—H13AC | 120.0 |
C10A—C11A—H11BA | 108.9 | C13C—C14C—C15C | 120.0 |
H11AA—C11A—H11BA | 107.7 | C13C—C14C—H14AC | 120.0 |
C13A—C12A—C17A | 116.9 (6) | C15C—C14C—H14AC | 120.0 |
C13A—C12A—C11A | 121.9 (5) | C16C—C15C—C14C | 120.0 |
C17A—C12A—C11A | 121.2 (6) | C16C—C15C—H15AC | 120.0 |
C12A—C13A—C14A | 121.9 (6) | C14C—C15C—H15AC | 120.0 |
C12A—C13A—H13A | 119.0 | C15C—C16C—C17C | 120.0 |
C14A—C13A—H13A | 119.0 | C15C—C16C—H16AC | 120.0 |
C15A—C14A—C13A | 120.6 (6) | C17C—C16C—H16AC | 120.0 |
C15A—C14A—H14A | 119.7 | C16C—C17C—C12C | 120.0 |
C13A—C14A—H14A | 119.7 | C16C—C17C—H17AC | 120.0 |
C14A—C15A—C16A | 118.3 (6) | C12C—C17C—H17AC | 120.0 |
C14A—C15A—H15A | 120.8 | C13'C—C12'C—C17'C | 120.0 |
C16A—C15A—H15A | 120.8 | C13'C—C12'C—C11C | 120.1 |
C15A—C16A—C17A | 121.0 (7) | C17'C—C12'C—C11C | 119.9 |
C15A—C16A—H16A | 119.5 | C12'C—C13'C—C14'C | 120.0 |
C17A—C16A—H16A | 119.5 | C12'C—C13'C—H13'C | 120.0 |
C12A—C17A—C16A | 121.3 (7) | C14'C—C13'C—H13'C | 120.0 |
C12A—C17A—H17A | 119.4 | C15'C—C14'C—C13'C | 118.5 |
C16A—C17A—H17A | 119.4 | C15'C—C14'C—H14'C | 120.0 |
O18A—C18A—O19A | 125.8 (5) | C13'C—C14'C—H14'C | 120.0 |
O18A—C18A—C10A | 119.9 (4) | C14'C—C15'C—C16'C | 120.0 |
O19A—C18A—C10A | 114.2 (4) | C14'C—C15'C—H15'C | 117.8 |
C6B—N1B—C2B | 121.0 (4) | C16'C—C15'C—H15'C | 121.6 |
C6B—N1B—C7B | 121.1 (4) | C17'C—C16'C—C15'C | 121.5 |
C2B—N1B—C7B | 117.7 (4) | C17'C—C16'C—H16'C | 118.0 |
O2B—C2B—N3B | 122.0 (4) | C15'C—C16'C—H16'C | 120.0 |
O2B—C2B—N1B | 121.3 (5) | C16'C—C17'C—C12'C | 120.0 |
N3B—C2B—N1B | 116.7 (4) | C16'C—C17'C—H17'C | 121.0 |
C4B—N3B—C2B | 121.9 (5) | C12'C—C17'C—H17'C | 120.0 |
C4B—N3B—H3B | 119.0 | O19C—C18C—O18C | 125.1 (5) |
C2B—N3B—H3B | 119.0 | O19C—C18C—C10C | 122.8 (5) |
N4B—C4B—N3B | 117.6 (5) | O18C—C18C—C10C | 112.1 (4) |
N4B—C4B—C5B | 122.2 (5) | C6D—N1D—C2D | 120.7 (4) |
N3B—C4B—C5B | 120.2 (5) | C6D—N1D—C7D | 120.8 (4) |
C4B—N4B—H4AB | 120.0 | C2D—N1D—C7D | 118.3 (4) |
C4B—N4B—H4BB | 120.0 | O2D—C2D—N3D | 123.3 (4) |
H4AB—N4B—H4BB | 120.0 | O2D—C2D—N1D | 121.3 (4) |
C6B—C5B—C4B | 118.1 (5) | N3D—C2D—N1D | 115.3 (4) |
C6B—C5B—H5B | 120.9 | C4D—N3D—C2D | 125.7 (4) |
C4B—C5B—H5B | 120.9 | C4D—N3D—H3D | 117.1 |
C5B—C6B—N1B | 121.7 (5) | C2D—N3D—H3D | 117.1 |
C5B—C6B—H6B | 119.2 | N4D—C4D—N3D | 119.7 (5) |
N1B—C6B—H6B | 119.2 | N4D—C4D—C5D | 123.2 (5) |
N1B—C7B—C8B | 112.2 (4) | N3D—C4D—C5D | 117.1 (5) |
N1B—C7B—H7AB | 109.2 | C4D—N4D—H4AD | 120.0 |
C8B—C7B—H7AB | 109.2 | C4D—N4D—H4BD | 120.0 |
N1B—C7B—H7BB | 109.2 | H4AD—N4D—H4BD | 120.0 |
C8B—C7B—H7BB | 109.2 | C6D—C5D—C4D | 118.4 (5) |
H7AB—C7B—H7BB | 107.9 | C6D—C5D—H5D | 120.8 |
C7B—C8B—C9B | 111.5 (4) | C4D—C5D—H5D | 120.8 |
C7B—C8B—H8AB | 109.3 | C5D—C6D—N1D | 122.6 (5) |
C9B—C8B—H8AB | 109.3 | C5D—C6D—H6D | 118.7 |
C7B—C8B—H8BB | 109.3 | N1D—C6D—H6D | 118.7 |
C9B—C8B—H8BB | 109.3 | N1D—C7D—C8D | 111.8 (4) |
H8AB—C8B—H8BB | 108.0 | N1D—C7D—H7AD | 109.2 |
O9B—C9B—N10B | 124.2 (5) | C8D—C7D—H7AD | 109.2 |
O9B—C9B—C8B | 120.0 (4) | N1D—C7D—H7BD | 109.2 |
N10B—C9B—C8B | 115.8 (4) | C8D—C7D—H7BD | 109.2 |
C9B—N10B—C10B | 119.9 (4) | H7AD—C7D—H7BD | 107.9 |
C9B—N10B—H10B | 120.0 | C9D—C8D—C7D | 109.7 (4) |
C10B—N10B—H10B | 120.0 | C9D—C8D—H8AD | 109.7 |
N10B—C10B—C11B | 110.3 (4) | C7D—C8D—H8AD | 109.7 |
N10B—C10B—C18B | 112.3 (4) | C9D—C8D—H8BD | 109.7 |
C11B—C10B—C18B | 108.1 (4) | C7D—C8D—H8BD | 109.7 |
N10B—C10B—H10AB | 108.7 | H8AD—C8D—H8BD | 108.2 |
C11B—C10B—H10AB | 108.7 | O9D—C9D—N10D | 122.4 (5) |
C18B—C10B—H10AB | 108.7 | O9D—C9D—C8D | 121.2 (5) |
C12B—C11B—C10B | 115.2 (4) | N10D—C9D—C8D | 116.4 (4) |
C12B—C11B—H11AB | 108.5 | C9D—N10D—C10D | 119.4 (4) |
C10B—C11B—H11AB | 108.5 | C9D—N10D—H10D | 120.3 |
C12B—C11B—H11BB | 108.5 | C10D—N10D—H10D | 120.3 |
C10B—C11B—H11BB | 108.5 | N10D—C10D—C11D | 111.8 (4) |
H11AB—C11B—H11BB | 107.5 | N10D—C10D—C18D | 111.2 (4) |
C17B—C12B—C13B | 118.9 (5) | C11D—C10D—C18D | 108.1 (4) |
C17B—C12B—C11B | 118.9 (5) | N10D—C10D—H10AD | 108.6 |
C13B—C12B—C11B | 122.1 (5) | C11D—C10D—H10AD | 108.5 |
C12B—C13B—C14B | 120.1 (5) | C18D—C10D—H10AD | 108.6 |
C12B—C13B—H13B | 119.9 | C12D—C11D—C10D | 114.1 (4) |
C14B—C13B—H13B | 119.9 | C12D—C11D—H11AD | 108.7 |
C15B—C14B—C13B | 119.9 (5) | C10D—C11D—H11AD | 108.7 |
C15B—C14B—H14B | 120.0 | C12D—C11D—H11BD | 108.7 |
C13B—C14B—H14B | 120.0 | C10D—C11D—H11BD | 108.7 |
C14B—C15B—C16B | 119.9 (6) | H11AD—C11D—H11BD | 107.6 |
C14B—C15B—H15B | 120.0 | C17D—C12D—C13D | 117.8 (5) |
C16B—C15B—H15B | 120.0 | C17D—C12D—C11D | 121.6 (5) |
C15B—C16B—C17B | 120.4 (6) | C13D—C12D—C11D | 120.7 (5) |
C15B—C16B—H16B | 119.8 | C12D—C13D—C14D | 120.5 (6) |
C17B—C16B—H16B | 119.8 | C12D—C13D—H13D | 119.7 |
C12B—C17B—C16B | 120.7 (5) | C14D—C13D—H13D | 119.7 |
C12B—C17B—H17B | 119.7 | C15D—C14D—C13D | 120.8 (6) |
C16B—C17B—H17B | 119.7 | C15D—C14D—H14D | 119.6 |
O18B—C18B—O19B | 125.9 (5) | C13D—C14D—H14D | 119.6 |
O18B—C18B—C10B | 120.0 (4) | C14D—C15D—C16D | 119.6 (6) |
O19B—C18B—C10B | 114.0 (4) | C14D—C15D—H15D | 120.2 |
C6C—N1C—C2C | 121.5 (4) | C16D—C15D—H15D | 120.2 |
C6C—N1C—C7C | 120.7 (4) | C15D—C16D—C17D | 119.8 (6) |
C2C—N1C—C7C | 117.7 (4) | C15D—C16D—H16D | 120.1 |
O2C—C2C—N3C | 122.1 (4) | C17D—C16D—H16D | 120.1 |
O2C—C2C—N1C | 122.6 (4) | C12D—C17D—C16D | 121.5 (6) |
N3C—C2C—N1C | 115.3 (4) | C12D—C17D—H17D | 119.2 |
C4C—N3C—C2C | 124.8 (4) | C16D—C17D—H17D | 119.2 |
C4C—N3C—H3C | 117.6 | O19D—C18D—O18D | 124.8 (5) |
C2C—N3C—H3C | 117.6 | O19D—C18D—C10D | 119.4 (4) |
N4C—C4C—N3C | 119.1 (5) | O18D—C18D—C10D | 115.8 (4) |
N4C—C4C—C5C | 123.3 (5) | ||
C6A—N1A—C2A—O2A | −177.0 (5) | C2C—N3C—C4C—N4C | −177.8 (5) |
C7A—N1A—C2A—O2A | 7.4 (7) | C2C—N3C—C4C—C5C | 3.5 (7) |
C6A—N1A—C2A—N3A | 3.2 (7) | N4C—C4C—C5C—C6C | −178.3 (5) |
C7A—N1A—C2A—N3A | −172.3 (4) | N3C—C4C—C5C—C6C | 0.4 (8) |
O2A—C2A—N3A—C4A | 179.5 (5) | C4C—C5C—C6C—N1C | −1.9 (9) |
N1A—C2A—N3A—C4A | −0.8 (7) | C2C—N1C—C6C—C5C | −0.3 (8) |
C2A—N3A—C4A—N4A | 178.8 (5) | C7C—N1C—C6C—C5C | −177.0 (5) |
C2A—N3A—C4A—C5A | −2.1 (8) | C6C—N1C—C7C—C8C | 98.5 (5) |
N4A—C4A—C5A—C6A | −178.2 (6) | C2C—N1C—C7C—C8C | −78.4 (5) |
N3A—C4A—C5A—C6A | 2.7 (9) | N1C—C7C—C8C—C9C | −61.1 (5) |
C4A—C5A—C6A—N1A | −0.4 (9) | C7C—C8C—C9C—O9C | −53.6 (6) |
C2A—N1A—C6A—C5A | −2.7 (8) | C7C—C8C—C9C—N10C | 124.4 (5) |
C7A—N1A—C6A—C5A | 172.7 (5) | O9C—C9C—N10C—C10C | −2.7 (7) |
C6A—N1A—C7A—C8A | 110.1 (5) | C8C—C9C—N10C—C10C | 179.2 (4) |
C2A—N1A—C7A—C8A | −74.4 (5) | C9C—N10C—C10C—C18C | −71.8 (6) |
N1A—C7A—C8A—C9A | −66.3 (5) | C9C—N10C—C10C—C11C | 164.5 (4) |
C7A—C8A—C9A—O9A | −30.3 (7) | N10C—C10C—C11C—C12C | −71.6 (5) |
C7A—C8A—C9A—N10A | 150.0 (4) | C18C—C10C—C11C—C12C | 165.1 (4) |
O9A—C9A—N10A—C10A | 1.4 (8) | N10C—C10C—C11C—C12'C | −77 (3) |
C8A—C9A—N10A—C10A | −178.8 (4) | C18C—C10C—C11C—C12'C | 160 (3) |
C9A—N10A—C10A—C11A | 135.4 (5) | C10C—C11C—C12C—C13C | 92.9 (4) |
C9A—N10A—C10A—C18A | −100.3 (5) | C10C—C11C—C12C—C17C | −83.9 (5) |
N10A—C10A—C11A—C12A | −53.9 (6) | C17C—C12C—C13C—C14C | 0.0 |
C18A—C10A—C11A—C12A | −179.7 (5) | C11C—C12C—C13C—C14C | −176.7 (4) |
C10A—C11A—C12A—C13A | −47.3 (8) | C12C—C13C—C14C—C15C | 0.0 |
C10A—C11A—C12A—C17A | 133.7 (6) | C13C—C14C—C15C—C16C | 0.0 |
C17A—C12A—C13A—C14A | 0.4 (9) | C14C—C15C—C16C—C17C | 0.0 |
C11A—C12A—C13A—C14A | −178.6 (5) | C15C—C16C—C17C—C12C | 0.0 |
C12A—C13A—C14A—C15A | −1.1 (9) | C13C—C12C—C17C—C16C | 0.0 |
C13A—C14A—C15A—C16A | 0.5 (10) | C11C—C12C—C17C—C16C | 176.8 (4) |
C14A—C15A—C16A—C17A | 0.7 (12) | C10C—C11C—C12'C—C13'C | 93 (5) |
C13A—C12A—C17A—C16A | 0.8 (10) | C10C—C11C—C12'C—C17'C | −89 (5) |
C11A—C12A—C17A—C16A | 179.8 (7) | C17'C—C12'C—C13'C—C14'C | 0 |
C15A—C16A—C17A—C12A | −1.4 (13) | C11C—C12'C—C13'C—C14'C | 179 |
N10A—C10A—C18A—O18A | −35.2 (7) | C12'C—C13'C—C14'C—C15'C | −2 |
C11A—C10A—C18A—O18A | 89.3 (6) | C13'C—C14'C—C15'C—C16'C | 3 |
N10A—C10A—C18A—O19A | 146.5 (5) | C14'C—C15'C—C16'C—C17'C | −4 |
C11A—C10A—C18A—O19A | −89.0 (6) | C15'C—C16'C—C17'C—C12'C | 3 |
C6B—N1B—C2B—O2B | −172.4 (4) | C13'C—C12'C—C17'C—C16'C | −2 |
C7B—N1B—C2B—O2B | 3.0 (6) | C11C—C12'C—C17'C—C16'C | −179 (3) |
C6B—N1B—C2B—N3B | 6.6 (6) | N10C—C10C—C18C—O19C | −23.0 (7) |
C7B—N1B—C2B—N3B | −178.0 (4) | C11C—C10C—C18C—O19C | 100.3 (6) |
O2B—C2B—N3B—C4B | 172.5 (5) | N10C—C10C—C18C—O18C | 158.2 (4) |
N1B—C2B—N3B—C4B | −6.5 (7) | C11C—C10C—C18C—O18C | −78.6 (6) |
C2B—N3B—C4B—N4B | −177.5 (5) | C6D—N1D—C2D—O2D | −175.8 (5) |
C2B—N3B—C4B—C5B | 3.3 (8) | C7D—N1D—C2D—O2D | 1.0 (7) |
N4B—C4B—C5B—C6B | −179.1 (5) | C6D—N1D—C2D—N3D | 2.4 (7) |
N3B—C4B—C5B—C6B | 0.1 (8) | C7D—N1D—C2D—N3D | 179.2 (4) |
C4B—C5B—C6B—N1B | 0.1 (8) | O2D—C2D—N3D—C4D | 173.9 (5) |
C2B—N1B—C6B—C5B | −3.6 (7) | N1D—C2D—N3D—C4D | −4.3 (7) |
C7B—N1B—C6B—C5B | −178.8 (5) | C2D—N3D—C4D—N4D | −177.8 (5) |
C6B—N1B—C7B—C8B | 97.0 (5) | C2D—N3D—C4D—C5D | 2.9 (8) |
C2B—N1B—C7B—C8B | −78.4 (5) | N4D—C4D—C5D—C6D | −178.8 (6) |
N1B—C7B—C8B—C9B | −61.7 (5) | N3D—C4D—C5D—C6D | 0.5 (8) |
C7B—C8B—C9B—O9B | −32.8 (6) | C4D—C5D—C6D—N1D | −2.2 (9) |
C7B—C8B—C9B—N10B | 148.0 (4) | C2D—N1D—C6D—C5D | 0.7 (8) |
O9B—C9B—N10B—C10B | 0.7 (7) | C7D—N1D—C6D—C5D | −176.1 (5) |
C8B—C9B—N10B—C10B | 179.9 (4) | C6D—N1D—C7D—C8D | 96.3 (5) |
C9B—N10B—C10B—C11B | 141.4 (5) | C2D—N1D—C7D—C8D | −80.6 (5) |
C9B—N10B—C10B—C18B | −98.0 (5) | N1D—C7D—C8D—C9D | −64.2 (5) |
N10B—C10B—C11B—C12B | −63.7 (6) | C7D—C8D—C9D—O9D | −54.7 (6) |
C18B—C10B—C11B—C12B | 173.1 (4) | C7D—C8D—C9D—N10D | 124.2 (4) |
C10B—C11B—C12B—C17B | 159.4 (5) | O9D—C9D—N10D—C10D | −2.7 (7) |
C10B—C11B—C12B—C13B | −24.7 (7) | C8D—C9D—N10D—C10D | 178.4 (4) |
C17B—C12B—C13B—C14B | 2.1 (8) | C9D—N10D—C10D—C11D | 163.8 (4) |
C11B—C12B—C13B—C14B | −173.8 (5) | C9D—N10D—C10D—C18D | −75.3 (6) |
C12B—C13B—C14B—C15B | −0.9 (9) | N10D—C10D—C11D—C12D | −59.8 (6) |
C13B—C14B—C15B—C16B | −0.3 (9) | C18D—C10D—C11D—C12D | 177.5 (4) |
C14B—C15B—C16B—C17B | 0.1 (10) | C10D—C11D—C12D—C17D | −81.6 (6) |
C13B—C12B—C17B—C16B | −2.3 (9) | C10D—C11D—C12D—C13D | 99.0 (6) |
C11B—C12B—C17B—C16B | 173.8 (5) | C17D—C12D—C13D—C14D | 1.0 (8) |
C15B—C16B—C17B—C12B | 1.2 (10) | C11D—C12D—C13D—C14D | −179.6 (5) |
N10B—C10B—C18B—O18B | −36.9 (6) | C12D—C13D—C14D—C15D | −0.2 (9) |
C11B—C10B—C18B—O18B | 85.0 (5) | C13D—C14D—C15D—C16D | −0.3 (10) |
N10B—C10B—C18B—O19B | 147.0 (4) | C14D—C15D—C16D—C17D | 0.1 (10) |
C11B—C10B—C18B—O19B | −91.0 (5) | C13D—C12D—C17D—C16D | −1.3 (9) |
C6C—N1C—C2C—O2C | −174.9 (5) | C11D—C12D—C17D—C16D | 179.4 (6) |
C7C—N1C—C2C—O2C | 2.0 (7) | C15D—C16D—C17D—C12D | 0.7 (10) |
C6C—N1C—C2C—N3C | 3.8 (7) | N10D—C10D—C18D—O19D | −28.5 (6) |
C7C—N1C—C2C—N3C | −179.4 (4) | C11D—C10D—C18D—O19D | 94.6 (5) |
O2C—C2C—N3C—C4C | 173.2 (5) | N10D—C10D—C18D—O18D | 153.1 (4) |
N1C—C2C—N3C—C4C | −5.5 (7) | C11D—C10D—C18D—O18D | −83.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O18Di | 0.88 | 1.75 | 2.623 (6) | 171 |
N4A—H4AA···O19Di | 0.88 | 1.94 | 2.811 (7) | 173 |
N10A—H10A···O19Cii | 0.88 | 2.19 | 3.036 (6) | 161 |
N3B—H3B···O18Ciii | 0.88 | 1.73 | 2.565 (6) | 159 |
N4B—H4AB···O19Ciii | 0.88 | 2.14 | 2.965 (7) | 156 |
N4B—H4BB···O2Aiv | 0.88 | 2.42 | 2.934 (7) | 118 |
N10B—H10B···O19Di | 0.88 | 2.05 | 2.885 (6) | 159 |
N3C—H3C···O19B | 0.88 | 1.74 | 2.601 (5) | 167 |
N4C—H4AC···O18B | 0.88 | 2.05 | 2.903 (6) | 164 |
N4C—H4BC···O19Av | 0.88 | 2.28 | 3.090 (7) | 154 |
N10C—H10C···O18Avi | 0.88 | 2.03 | 2.890 (5) | 167 |
N3D—H3D···O19Avi | 0.88 | 1.75 | 2.615 (5) | 168 |
N4D—H4AD···O18Avi | 0.88 | 2.06 | 2.920 (6) | 165 |
N4D—H4BD···O19B | 0.88 | 2.23 | 3.047 (6) | 155 |
N10D—H10D···O18Biv | 0.88 | 2.10 | 2.945 (5) | 162 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z−1; (iii) x+1, y, z−1; (iv) x, y−1, z; (v) x−1, y, z+1; (vi) x−1, y−1, z+1. |
C10H14N4O5·H2O | Z = 2 |
Mr = 288.27 | F(000) = 304 |
Triclinic, P1 | Dx = 1.516 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.863 (1) Å | Cell parameters from 1717 reflections |
b = 10.771 (2) Å | θ = 3.4–28.7° |
c = 12.228 (2) Å | µ = 0.13 mm−1 |
α = 80.45 (3)° | T = 100 K |
β = 89.23 (3)° | Plate, colourless |
γ = 88.61 (3)° | 0.25 × 0.25 × 0.06 mm |
V = 631.4 (2) Å3 |
Bruker SMART APEX diffractometer | 2336 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 2284 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.366 pixels mm-1 | θmax = 25.7°, θmin = 1.7° |
ω scans | h = −5→4 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −10→13 |
Tmin = 0.827, Tmax = 0.993 | l = −14→14 |
3919 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0615P)2 + 0.1838P] where P = (Fo2 + 2Fc2)/3 |
2336 reflections | (Δ/σ)max = 0.007 |
377 parameters | Δρmax = 0.32 e Å−3 |
3 restraints | Δρmin = −0.25 e Å−3 |
C10H14N4O5·H2O | γ = 88.61 (3)° |
Mr = 288.27 | V = 631.4 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 4.863 (1) Å | Mo Kα radiation |
b = 10.771 (2) Å | µ = 0.13 mm−1 |
c = 12.228 (2) Å | T = 100 K |
α = 80.45 (3)° | 0.25 × 0.25 × 0.06 mm |
β = 89.23 (3)° |
Bruker SMART APEX diffractometer | 2336 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2284 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 0.993 | Rint = 0.022 |
3919 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 3 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.32 e Å−3 |
2336 reflections | Δρmin = −0.25 e Å−3 |
377 parameters |
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 | ||
N1A | 0.9036 (7) | 0.2485 (3) | 0.2358 (3) | 0.0128 (7) | |
C2A | 1.1159 (8) | 0.1800 (4) | 0.2948 (3) | 0.0123 (8) | |
O2A | 1.1824 (6) | 0.1964 (3) | 0.3875 (2) | 0.0162 (6) | |
N3A | 1.2527 (7) | 0.0930 (3) | 0.2414 (3) | 0.0135 (7) | |
H3A | 1.3913 | 0.0502 | 0.2761 | 0.016* | |
C4A | 1.1896 (8) | 0.0681 (4) | 0.1388 (3) | 0.0118 (8) | |
N4A | 1.3306 (7) | −0.0180 (3) | 0.0976 (3) | 0.0150 (8) | |
H4AA | 1.4654 | −0.0597 | 0.1359 | 0.018* | |
H4BA | 1.2910 | −0.0345 | 0.0316 | 0.018* | |
C5A | 0.9696 (9) | 0.1400 (4) | 0.0815 (3) | 0.0152 (9) | |
H5A | 0.9183 | 0.1269 | 0.0097 | 0.018* | |
C6A | 0.8353 (8) | 0.2273 (4) | 0.1315 (3) | 0.0131 (8) | |
H6A | 0.6891 | 0.2755 | 0.0934 | 0.016* | |
C7A | 0.7538 (8) | 0.3456 (4) | 0.2875 (3) | 0.0129 (8) | |
H7AA | 0.7054 | 0.3104 | 0.3652 | 0.015* | |
H7BA | 0.5809 | 0.3703 | 0.2469 | 0.015* | |
C8A | 0.9314 (9) | 0.4620 (4) | 0.2852 (3) | 0.0149 (9) | |
H8AA | 1.1071 | 0.4366 | 0.3235 | 0.018* | |
H8BA | 0.9745 | 0.4986 | 0.2074 | 0.018* | |
C9A | 0.7850 (8) | 0.5600 (4) | 0.3412 (3) | 0.0122 (8) | |
O9A | 0.5310 (6) | 0.5628 (3) | 0.3529 (2) | 0.0173 (6) | |
N10A | 0.9470 (7) | 0.6443 (3) | 0.3756 (3) | 0.0126 (7) | |
H10A | 1.1263 | 0.6368 | 0.3671 | 0.015* | |
C10A | 0.8356 (8) | 0.7478 (4) | 0.4266 (3) | 0.0132 (8) | |
H10AA | 0.6816 | 0.7147 | 0.4773 | 0.016* | |
C11A | 1.0556 (9) | 0.7948 (4) | 0.4967 (3) | 0.0162 (9) | |
H11AA | 1.2166 | 0.8222 | 0.4491 | 0.019* | |
H11BA | 0.9819 | 0.8684 | 0.5273 | 0.019* | |
O11A | 1.1408 (7) | 0.6985 (3) | 0.5857 (3) | 0.0263 (8) | |
H11A | 1.1145 | 0.7240 | 0.6464 | 0.039* | |
C12A | 0.7197 (8) | 0.8587 (4) | 0.3416 (3) | 0.0125 (8) | |
O12A | 0.7184 (7) | 0.8470 (3) | 0.2413 (2) | 0.0201 (7) | |
O13A | 0.6306 (6) | 0.9549 (3) | 0.3792 (2) | 0.0159 (6) | |
N1B | 0.8068 (7) | 0.2635 (3) | 0.7485 (3) | 0.0152 (8) | |
C2B | 0.5983 (8) | 0.1943 (4) | 0.8047 (3) | 0.0117 (8) | |
O2B | 0.5115 (6) | 0.2101 (3) | 0.8950 (2) | 0.0176 (7) | |
N3B | 0.4905 (7) | 0.1026 (3) | 0.7497 (3) | 0.0119 (7) | |
H3B | 0.3585 | 0.0561 | 0.7836 | 0.014* | |
C4B | 0.5731 (8) | 0.0793 (4) | 0.6474 (3) | 0.0118 (8) | |
N4B | 0.4556 (7) | −0.0093 (3) | 0.6049 (3) | 0.0147 (8) | |
H4AB | 0.3243 | −0.0535 | 0.6419 | 0.018* | |
H4BB | 0.5077 | −0.0248 | 0.5392 | 0.018* | |
C5B | 0.7866 (9) | 0.1556 (4) | 0.5935 (4) | 0.0163 (9) | |
H5B | 0.8526 | 0.1442 | 0.5223 | 0.020* | |
C6B | 0.8926 (9) | 0.2438 (4) | 0.6451 (3) | 0.0167 (9) | |
H6B | 1.0334 | 0.2951 | 0.6085 | 0.020* | |
C7B | 0.9290 (9) | 0.3646 (4) | 0.8000 (4) | 0.0166 (9) | |
H7AB | 1.1147 | 0.3828 | 0.7680 | 0.020* | |
H7BB | 0.9491 | 0.3352 | 0.8806 | 0.020* | |
C8B | 0.7530 (9) | 0.4845 (4) | 0.7813 (4) | 0.0185 (9) | |
H8AB | 0.5674 | 0.4663 | 0.8134 | 0.022* | |
H8BB | 0.7327 | 0.5139 | 0.7007 | 0.022* | |
C9B | 0.8782 (8) | 0.5881 (4) | 0.8339 (3) | 0.0130 (9) | |
O9B | 1.1280 (6) | 0.5869 (3) | 0.8556 (2) | 0.0164 (6) | |
N10B | 0.7037 (7) | 0.6815 (3) | 0.8520 (3) | 0.0135 (7) | |
H10B | 0.5304 | 0.6778 | 0.8332 | 0.016* | |
C10B | 0.7891 (9) | 0.7895 (4) | 0.9017 (3) | 0.0134 (8) | |
H10AB | 0.6227 | 0.8459 | 0.9016 | 0.016* | |
C11B | 0.8679 (9) | 0.7501 (4) | 1.0232 (3) | 0.0167 (9) | |
H11AB | 1.0245 | 0.6890 | 1.0290 | 0.020* | |
H11BB | 0.9255 | 0.8247 | 1.0540 | 0.020* | |
O11B | 0.6389 (7) | 0.6945 (3) | 1.0846 (2) | 0.0207 (7) | |
H11B | 0.6338 | 0.7164 | 1.1474 | 0.031* | |
C12B | 1.0092 (8) | 0.8683 (4) | 0.8336 (3) | 0.0131 (8) | |
O12B | 1.0536 (7) | 0.8548 (3) | 0.7350 (2) | 0.0214 (7) | |
O13B | 1.1254 (6) | 0.9495 (3) | 0.8803 (2) | 0.0165 (6) | |
O1C | 0.3425 (7) | 0.4514 (3) | 0.5734 (3) | 0.0235 (7) | |
H1C | 0.244 (11) | 0.527 (5) | 0.565 (4) | 0.017 (12)* | |
H2C | 0.420 (14) | 0.465 (6) | 0.507 (5) | 0.045 (18)* | |
O1D | 0.4008 (8) | 0.4616 (3) | 1.0599 (3) | 0.0265 (8) | |
H1D | 0.523 (17) | 0.525 (7) | 1.047 (6) | 0.07 (2)* | |
H2D | 0.306 (15) | 0.484 (6) | 1.007 (6) | 0.05 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0167 (19) | 0.0098 (17) | 0.0124 (17) | −0.0012 (14) | 0.0002 (14) | −0.0033 (13) |
C2A | 0.013 (2) | 0.011 (2) | 0.013 (2) | −0.0029 (16) | 0.0027 (16) | −0.0031 (16) |
O2A | 0.0217 (16) | 0.0171 (15) | 0.0103 (14) | 0.0024 (12) | −0.0024 (12) | −0.0041 (11) |
N3A | 0.0136 (17) | 0.0144 (17) | 0.0124 (17) | 0.0030 (14) | −0.0049 (14) | −0.0019 (13) |
C4A | 0.015 (2) | 0.0092 (19) | 0.0121 (19) | −0.0073 (16) | −0.0009 (16) | −0.0023 (15) |
N4A | 0.0193 (19) | 0.0179 (19) | 0.0095 (16) | 0.0012 (15) | −0.0030 (14) | −0.0070 (13) |
C5A | 0.018 (2) | 0.019 (2) | 0.0096 (19) | −0.0057 (17) | −0.0025 (16) | −0.0015 (16) |
C6A | 0.013 (2) | 0.012 (2) | 0.015 (2) | −0.0047 (16) | −0.0022 (16) | −0.0032 (15) |
C7A | 0.011 (2) | 0.012 (2) | 0.016 (2) | 0.0016 (16) | 0.0042 (16) | −0.0051 (16) |
C8A | 0.014 (2) | 0.015 (2) | 0.016 (2) | −0.0026 (16) | 0.0020 (16) | −0.0030 (16) |
C9A | 0.016 (2) | 0.010 (2) | 0.0108 (19) | −0.0009 (16) | −0.0003 (16) | −0.0026 (15) |
O9A | 0.0106 (15) | 0.0223 (16) | 0.0212 (15) | −0.0035 (12) | 0.0017 (11) | −0.0095 (12) |
N10A | 0.0081 (17) | 0.0173 (18) | 0.0126 (17) | 0.0056 (14) | −0.0002 (13) | −0.0037 (13) |
C10A | 0.015 (2) | 0.012 (2) | 0.0127 (19) | −0.0003 (16) | 0.0013 (16) | −0.0043 (15) |
C11A | 0.020 (2) | 0.017 (2) | 0.014 (2) | 0.0020 (17) | −0.0053 (17) | −0.0072 (16) |
O11A | 0.042 (2) | 0.0209 (17) | 0.0174 (16) | 0.0131 (15) | −0.0146 (15) | −0.0082 (13) |
C12A | 0.0098 (19) | 0.014 (2) | 0.015 (2) | −0.0017 (16) | −0.0007 (15) | −0.0071 (16) |
O12A | 0.0317 (19) | 0.0192 (16) | 0.0108 (14) | 0.0070 (13) | −0.0036 (13) | −0.0077 (12) |
O13A | 0.0204 (16) | 0.0145 (15) | 0.0135 (14) | 0.0035 (12) | −0.0039 (12) | −0.0050 (11) |
N1B | 0.0156 (19) | 0.0151 (18) | 0.0143 (18) | −0.0030 (14) | −0.0045 (15) | −0.0001 (14) |
C2B | 0.011 (2) | 0.009 (2) | 0.014 (2) | 0.0052 (16) | −0.0067 (16) | 0.0010 (15) |
O2B | 0.0207 (17) | 0.0223 (17) | 0.0103 (15) | 0.0014 (13) | −0.0001 (12) | −0.0045 (12) |
N3B | 0.0099 (17) | 0.0110 (17) | 0.0148 (16) | −0.0023 (13) | −0.0013 (13) | −0.0014 (13) |
C4B | 0.0111 (19) | 0.013 (2) | 0.0098 (19) | 0.0050 (16) | −0.0013 (15) | 0.0020 (15) |
N4B | 0.0196 (19) | 0.0137 (18) | 0.0112 (17) | −0.0008 (15) | 0.0015 (14) | −0.0033 (14) |
C5B | 0.017 (2) | 0.015 (2) | 0.017 (2) | 0.0024 (17) | −0.0002 (17) | −0.0014 (17) |
C6B | 0.016 (2) | 0.017 (2) | 0.016 (2) | −0.0003 (17) | 0.0039 (17) | 0.0024 (17) |
C7B | 0.020 (2) | 0.011 (2) | 0.018 (2) | −0.0033 (17) | −0.0057 (17) | −0.0022 (17) |
C8B | 0.022 (2) | 0.014 (2) | 0.019 (2) | −0.0011 (18) | −0.0034 (19) | −0.0036 (17) |
C9B | 0.013 (2) | 0.017 (2) | 0.0082 (18) | −0.0010 (16) | −0.0013 (16) | −0.0019 (16) |
O9B | 0.0126 (15) | 0.0172 (16) | 0.0213 (16) | −0.0014 (12) | −0.0031 (12) | −0.0082 (12) |
N10B | 0.0100 (17) | 0.0175 (18) | 0.0147 (17) | −0.0040 (14) | −0.0024 (14) | −0.0068 (14) |
C10B | 0.016 (2) | 0.015 (2) | 0.0102 (19) | −0.0017 (16) | 0.0007 (15) | −0.0033 (15) |
C11B | 0.023 (2) | 0.017 (2) | 0.011 (2) | −0.0040 (18) | −0.0017 (17) | −0.0039 (16) |
O11B | 0.0301 (18) | 0.0226 (16) | 0.0108 (14) | −0.0114 (14) | 0.0086 (13) | −0.0056 (12) |
C12B | 0.012 (2) | 0.013 (2) | 0.015 (2) | 0.0003 (16) | −0.0029 (16) | −0.0049 (16) |
O12B | 0.0333 (19) | 0.0214 (17) | 0.0115 (15) | −0.0102 (14) | 0.0072 (13) | −0.0074 (12) |
O13B | 0.0204 (16) | 0.0180 (15) | 0.0118 (14) | −0.0085 (12) | 0.0029 (11) | −0.0040 (11) |
O1C | 0.0296 (19) | 0.0199 (18) | 0.0197 (17) | 0.0019 (15) | 0.0018 (14) | 0.0001 (13) |
O1D | 0.032 (2) | 0.0205 (18) | 0.0253 (18) | −0.0024 (15) | −0.0107 (16) | 0.0006 (14) |
N1A—C6A | 1.378 (5) | N1B—C7B | 1.485 (5) |
N1A—C2A | 1.392 (5) | C2B—O2B | 1.214 (5) |
N1A—C7A | 1.482 (5) | C2B—N3B | 1.398 (5) |
C2A—O2A | 1.224 (5) | N3B—C4B | 1.369 (5) |
C2A—N3A | 1.382 (5) | N3B—H3B | 0.8800 |
N3A—C4A | 1.366 (5) | C4B—N4B | 1.307 (5) |
N3A—H3A | 0.8800 | C4B—C5B | 1.425 (6) |
C4A—N4A | 1.304 (6) | N4B—H4AB | 0.8800 |
C4A—C5A | 1.426 (6) | N4B—H4BB | 0.8800 |
N4A—H4AA | 0.8800 | C5B—C6B | 1.341 (6) |
N4A—H4BA | 0.8800 | C5B—H5B | 0.9500 |
C5A—C6A | 1.354 (6) | C6B—H6B | 0.9500 |
C5A—H5A | 0.9500 | C7B—C8B | 1.519 (6) |
C6A—H6A | 0.9500 | C7B—H7AB | 0.9900 |
C7A—C8A | 1.536 (6) | C7B—H7BB | 0.9900 |
C7A—H7AA | 0.9900 | C8B—C9B | 1.520 (6) |
C7A—H7BA | 0.9900 | C8B—H8AB | 0.9900 |
C8A—C9A | 1.510 (6) | C8B—H8BB | 0.9900 |
C8A—H8AA | 0.9900 | C9B—O9B | 1.246 (5) |
C8A—H8BA | 0.9900 | C9B—N10B | 1.345 (5) |
C9A—O9A | 1.242 (5) | N10B—C10B | 1.470 (5) |
C9A—N10A | 1.339 (5) | N10B—H10B | 0.8800 |
N10A—C10A | 1.456 (5) | C10B—C11B | 1.527 (5) |
N10A—H10A | 0.8800 | C10B—C12B | 1.532 (6) |
C10A—C11A | 1.526 (6) | C10B—H10AB | 1.0000 |
C10A—C12A | 1.548 (6) | C11B—O11B | 1.422 (5) |
C10A—H10AA | 1.0000 | C11B—H11AB | 0.9900 |
C11A—O11A | 1.431 (5) | C11B—H11BB | 0.9900 |
C11A—H11AA | 0.9900 | O11B—H11B | 0.8400 |
C11A—H11BA | 0.9900 | C12B—O12B | 1.253 (5) |
O11A—H11A | 0.8400 | C12B—O13B | 1.269 (5) |
C12A—O12A | 1.253 (5) | O1C—H1C | 0.93 (6) |
C12A—O13A | 1.266 (5) | O1C—H2C | 0.88 (7) |
N1B—C2B | 1.380 (5) | O1D—H1D | 0.91 (8) |
N1B—C6B | 1.374 (6) | O1D—H2D | 0.80 (7) |
C6A—N1A—C2A | 121.0 (4) | C2B—N1B—C7B | 118.5 (3) |
C6A—N1A—C7A | 120.7 (3) | C6B—N1B—C7B | 120.2 (4) |
C2A—N1A—C7A | 118.3 (3) | O2B—C2B—N1B | 123.6 (4) |
O2A—C2A—N3A | 121.5 (4) | O2B—C2B—N3B | 121.4 (4) |
O2A—C2A—N1A | 122.8 (4) | N1B—C2B—N3B | 115.0 (4) |
N3A—C2A—N1A | 115.8 (3) | C4B—N3B—C2B | 125.4 (4) |
C4A—N3A—C2A | 125.1 (4) | C4B—N3B—H3B | 117.3 |
C4A—N3A—H3A | 117.5 | C2B—N3B—H3B | 117.3 |
C2A—N3A—H3A | 117.5 | N4B—C4B—N3B | 119.5 (4) |
N4A—C4A—N3A | 119.5 (4) | N4B—C4B—C5B | 123.9 (4) |
N4A—C4A—C5A | 123.2 (4) | N3B—C4B—C5B | 116.6 (4) |
N3A—C4A—C5A | 117.2 (4) | C4B—N4B—H4AB | 120.0 |
C4A—N4A—H4AA | 120.0 | C4B—N4B—H4BB | 120.0 |
C4A—N4A—H4BA | 120.0 | H4AB—N4B—H4BB | 120.0 |
H4AA—N4A—H4BA | 120.0 | C6B—C5B—C4B | 118.8 (4) |
C6A—C5A—C4A | 118.7 (4) | C6B—C5B—H5B | 120.6 |
C6A—C5A—H5A | 120.6 | C4B—C5B—H5B | 120.6 |
C4A—C5A—H5A | 120.6 | C5B—C6B—N1B | 123.0 (4) |
C5A—C6A—N1A | 122.2 (4) | C5B—C6B—H6B | 118.5 |
C5A—C6A—H6A | 118.9 | N1B—C6B—H6B | 118.5 |
N1A—C6A—H6A | 118.9 | N1B—C7B—C8B | 111.7 (3) |
N1A—C7A—C8A | 110.5 (3) | N1B—C7B—H7AB | 109.3 |
N1A—C7A—H7AA | 109.5 | C8B—C7B—H7AB | 109.3 |
C8A—C7A—H7AA | 109.5 | N1B—C7B—H7BB | 109.3 |
N1A—C7A—H7BA | 109.5 | C8B—C7B—H7BB | 109.3 |
C8A—C7A—H7BA | 109.5 | H7AB—C7B—H7BB | 107.9 |
H7AA—C7A—H7BA | 108.1 | C7B—C8B—C9B | 111.7 (4) |
C9A—C8A—C7A | 111.1 (3) | C7B—C8B—H8AB | 109.3 |
C9A—C8A—H8AA | 109.4 | C9B—C8B—H8AB | 109.3 |
C7A—C8A—H8AA | 109.4 | C7B—C8B—H8BB | 109.3 |
C9A—C8A—H8BA | 109.4 | C9B—C8B—H8BB | 109.3 |
C7A—C8A—H8BA | 109.4 | H8AB—C8B—H8BB | 107.9 |
H8AA—C8A—H8BA | 108.0 | O9B—C9B—N10B | 122.9 (4) |
O9A—C9A—N10A | 122.5 (4) | O9B—C9B—C8B | 121.5 (4) |
O9A—C9A—C8A | 122.0 (4) | N10B—C9B—C8B | 115.6 (3) |
N10A—C9A—C8A | 115.5 (4) | C9B—N10B—C10B | 123.0 (3) |
C9A—N10A—C10A | 122.0 (3) | C9B—N10B—H10B | 118.5 |
C9A—N10A—H10A | 119.0 | C10B—N10B—H10B | 118.5 |
C10A—N10A—H10A | 119.0 | N10B—C10B—C11B | 111.7 (3) |
N10A—C10A—C11A | 109.9 (3) | N10B—C10B—C12B | 113.4 (3) |
N10A—C10A—C12A | 113.3 (3) | C11B—C10B—C12B | 112.8 (3) |
C11A—C10A—C12A | 109.9 (3) | N10B—C10B—H10AB | 106.1 |
N10A—C10A—H10AA | 107.9 | C11B—C10B—H10AB | 106.1 |
C11A—C10A—H10AA | 107.9 | C12B—C10B—H10AB | 106.1 |
C12A—C10A—H10AA | 107.9 | O11B—C11B—C10B | 109.6 (3) |
O11A—C11A—C10A | 111.3 (4) | O11B—C11B—H11AB | 109.7 |
O11A—C11A—H11AA | 109.4 | C10B—C11B—H11AB | 109.7 |
C10A—C11A—H11AA | 109.4 | O11B—C11B—H11BB | 109.7 |
O11A—C11A—H11BA | 109.4 | C10B—C11B—H11BB | 109.7 |
C10A—C11A—H11BA | 109.4 | H11AB—C11B—H11BB | 108.2 |
H11AA—C11A—H11BA | 108.0 | C11B—O11B—H11B | 109.5 |
C11A—O11A—H11A | 109.5 | O12B—C12B—O13B | 124.0 (4) |
O12A—C12A—O13A | 124.7 (4) | O12B—C12B—C10B | 119.4 (3) |
O12A—C12A—C10A | 118.3 (4) | O13B—C12B—C10B | 116.5 (4) |
O13A—C12A—C10A | 117.0 (3) | H1C—O1C—H2C | 95 (5) |
C2B—N1B—C6B | 121.2 (4) | H1D—O1D—H2D | 97 (6) |
C6A—N1A—C2A—O2A | 180.0 (4) | C6B—N1B—C2B—O2B | −178.3 (4) |
C7A—N1A—C2A—O2A | 0.4 (5) | C7B—N1B—C2B—O2B | −1.2 (6) |
C6A—N1A—C2A—N3A | 1.1 (5) | C6B—N1B—C2B—N3B | 1.6 (5) |
C7A—N1A—C2A—N3A | −178.5 (3) | C7B—N1B—C2B—N3B | 178.7 (3) |
O2A—C2A—N3A—C4A | 179.2 (4) | O2B—C2B—N3B—C4B | 179.2 (4) |
N1A—C2A—N3A—C4A | −1.9 (6) | N1B—C2B—N3B—C4B | −0.8 (5) |
C2A—N3A—C4A—N4A | −178.7 (4) | C2B—N3B—C4B—N4B | 180.0 (3) |
C2A—N3A—C4A—C5A | 1.6 (6) | C2B—N3B—C4B—C5B | −0.1 (6) |
N4A—C4A—C5A—C6A | 179.9 (4) | N4B—C4B—C5B—C6B | −179.9 (4) |
N3A—C4A—C5A—C6A | −0.5 (6) | N3B—C4B—C5B—C6B | 0.2 (6) |
C4A—C5A—C6A—N1A | −0.2 (6) | C4B—C5B—C6B—N1B | 0.7 (6) |
C2A—N1A—C6A—C5A | −0.1 (6) | C2B—N1B—C6B—C5B | −1.7 (6) |
C7A—N1A—C6A—C5A | 179.4 (4) | C7B—N1B—C6B—C5B | −178.8 (4) |
C6A—N1A—C7A—C8A | −105.4 (4) | C2B—N1B—C7B—C8B | −80.8 (4) |
C2A—N1A—C7A—C8A | 74.2 (4) | C6B—N1B—C7B—C8B | 96.4 (5) |
N1A—C7A—C8A—C9A | −178.1 (3) | N1B—C7B—C8B—C9B | −179.9 (3) |
C7A—C8A—C9A—O9A | −21.7 (5) | C7B—C8B—C9B—O9B | 21.5 (6) |
C7A—C8A—C9A—N10A | 159.2 (3) | C7B—C8B—C9B—N10B | −160.2 (4) |
O9A—C9A—N10A—C10A | −1.8 (6) | O9B—C9B—N10B—C10B | −1.6 (6) |
C8A—C9A—N10A—C10A | 177.3 (3) | C8B—C9B—N10B—C10B | −179.8 (3) |
C9A—N10A—C10A—C11A | 157.7 (4) | C9B—N10B—C10B—C11B | −67.9 (5) |
C9A—N10A—C10A—C12A | −79.0 (4) | C9B—N10B—C10B—C12B | 60.9 (5) |
N10A—C10A—C11A—O11A | −62.5 (5) | N10B—C10B—C11B—O11B | −59.8 (5) |
C12A—C10A—C11A—O11A | 172.2 (3) | C12B—C10B—C11B—O11B | 171.1 (3) |
N10A—C10A—C12A—O12A | 3.7 (5) | N10B—C10B—C12B—O12B | 15.5 (5) |
C11A—C10A—C12A—O12A | 127.0 (4) | C11B—C10B—C12B—O12B | 143.7 (4) |
N10A—C10A—C12A—O13A | −176.8 (3) | N10B—C10B—C12B—O13B | −168.4 (4) |
C11A—C10A—C12A—O13A | −53.5 (5) | C11B—C10B—C12B—O13B | −40.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O13Ai | 0.88 | 1.88 | 2.747 (4) | 167 |
N4A—H4AA···O12Ai | 0.88 | 1.93 | 2.805 (5) | 170 |
N4A—H4BA···O13Bii | 0.88 | 2.06 | 2.928 (5) | 168 |
N10A—H10A···O9Aiii | 0.88 | 2.12 | 2.975 (5) | 163 |
O11A—H11A···O12B | 0.84 | 1.93 | 2.704 (5) | 153 |
N3B—H3B···O13Biv | 0.88 | 1.89 | 2.759 (4) | 168 |
N4B—H4AB···O12Biv | 0.88 | 1.91 | 2.789 (5) | 174 |
N4B—H4BB···O13Av | 0.88 | 2.08 | 2.960 (5) | 175 |
N10B—H10B···O9Bvi | 0.88 | 2.20 | 3.000 (5) | 150 |
O11B—H11B···O12Avii | 0.84 | 2.01 | 2.759 (4) | 148 |
O1C—H1C···O11Avi | 0.93 (5) | 1.96 (6) | 2.841 (5) | 159 (5) |
O1C—H2C···O9A | 0.88 (6) | 2.07 (6) | 2.909 (4) | 158 (6) |
O1D—H1D···O11B | 0.91 (8) | 2.05 (8) | 2.851 (5) | 146 (7) |
O1D—H2D···O9Bvi | 0.80 (7) | 2.17 (7) | 2.951 (4) | 164 (7) |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z−1; (iii) x+1, y, z; (iv) x−1, y−1, z; (v) x, y−1, z; (vi) x−1, y, z; (vii) x, y, z+1. |
C13H21N5O4 | Z = 2 |
Mr = 311.35 | F(000) = 332 |
Triclinic, P1 | Dx = 1.424 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9334 (9) Å | Cell parameters from 2571 reflections |
b = 8.2977 (10) Å | θ = 2.5–26.8° |
c = 13.2491 (16) Å | µ = 0.11 mm−1 |
α = 90.780 (2)° | T = 100 K |
β = 93.498 (2)° | Plate, colourless |
γ = 107.293 (2)° | 0.40 × 0.18 × 0.04 mm |
V = 726.02 (16) Å3 |
Bruker SMART APEX diffractometer | 2970 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 2714 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.366 pixels mm-1 | θmax = 26.4°, θmin = 1.5° |
ω scans | h = −8→8 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.878, Tmax = 0.996 | l = −16→16 |
7954 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0707P)2 + 0.0541P] where P = (Fo2 + 2Fc2)/3 |
2970 reflections | (Δ/σ)max < 0.001 |
399 parameters | Δρmax = 0.34 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
C13H21N5O4 | γ = 107.293 (2)° |
Mr = 311.35 | V = 726.02 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9334 (9) Å | Mo Kα radiation |
b = 8.2977 (10) Å | µ = 0.11 mm−1 |
c = 13.2491 (16) Å | T = 100 K |
α = 90.780 (2)° | 0.40 × 0.18 × 0.04 mm |
β = 93.498 (2)° |
Bruker SMART APEX diffractometer | 2970 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2714 reflections with I > 2σ(I) |
Tmin = 0.878, Tmax = 0.996 | Rint = 0.025 |
7954 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 3 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.34 e Å−3 |
2970 reflections | Δρmin = −0.19 e Å−3 |
399 parameters |
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 | ||
N1A | 0.2314 (3) | −0.4276 (3) | 0.11002 (19) | 0.0163 (5) | |
C2A | 0.1058 (4) | −0.4228 (3) | 0.1884 (2) | 0.0153 (6) | |
O2A | 0.1817 (3) | −0.3322 (3) | 0.26411 (16) | 0.0216 (5) | |
N3A | −0.0903 (4) | −0.5144 (3) | 0.17714 (19) | 0.0177 (5) | |
C4A | −0.1667 (4) | −0.6059 (3) | 0.0913 (2) | 0.0165 (6) | |
N4A | −0.3620 (4) | −0.6916 (3) | 0.08249 (19) | 0.0203 (5) | |
H4A1 | −0.4393 | −0.6882 | 0.1323 | 0.024* | |
H4A2 | −0.4144 | −0.7520 | 0.0269 | 0.024* | |
C5A | −0.0404 (5) | −0.6137 (3) | 0.0114 (2) | 0.0186 (6) | |
H5A | −0.0934 | −0.6793 | −0.0489 | 0.022* | |
C6A | 0.1563 (5) | −0.5248 (3) | 0.0245 (2) | 0.0182 (6) | |
H6A | 0.2446 | −0.5297 | −0.0268 | 0.022* | |
C7A | 0.4452 (4) | −0.3250 (4) | 0.1216 (2) | 0.0192 (6) | |
H7A1 | 0.5230 | −0.3680 | 0.0732 | 0.023* | |
H7A2 | 0.5008 | −0.3364 | 0.1908 | 0.023* | |
C8A | 0.4715 (4) | −0.1383 (4) | 0.1030 (2) | 0.0176 (6) | |
H8A1 | 0.4028 | −0.0926 | 0.1547 | 0.021* | |
H8A2 | 0.6174 | −0.0745 | 0.1099 | 0.021* | |
C9A | 0.3840 (4) | −0.1139 (3) | −0.0019 (2) | 0.0159 (6) | |
O9A | 0.4195 (3) | −0.1864 (3) | −0.07727 (17) | 0.0230 (5) | |
N10A | 0.2662 (3) | −0.0123 (3) | −0.00709 (18) | 0.0145 (5) | |
H10A | 0.2496 | 0.0404 | 0.0483 | 0.017* | |
C10A | 0.1646 (4) | 0.0133 (3) | −0.1023 (2) | 0.0157 (6) | |
H10B | 0.1987 | −0.0600 | −0.1546 | 0.019* | |
C11A | −0.0647 (4) | −0.0518 (3) | −0.0949 (2) | 0.0185 (6) | |
H11A | −0.1329 | −0.0195 | −0.1557 | 0.022* | |
H11B | −0.1016 | 0.0024 | −0.0351 | 0.022* | |
C12A | −0.1396 (4) | −0.2435 (3) | −0.0860 (2) | 0.0191 (6) | |
H12A | −0.0471 | −0.2776 | −0.0367 | 0.023* | |
H12B | −0.2751 | −0.2746 | −0.0587 | 0.023* | |
C13A | −0.1540 (4) | −0.3436 (4) | −0.1856 (2) | 0.0244 (7) | |
H13A | −0.0252 | −0.2986 | −0.2185 | 0.029* | |
H13B | −0.1680 | −0.4626 | −0.1699 | 0.029* | |
C14A | −0.3269 (4) | −0.3401 (4) | −0.2607 (2) | 0.0217 (6) | |
H14A | −0.3137 | −0.2217 | −0.2776 | 0.026* | |
H14B | −0.3181 | −0.4022 | −0.3237 | 0.026* | |
N14A | −0.5282 (4) | −0.4174 (3) | −0.2198 (2) | 0.0192 (5) | |
H14C | −0.5308 | −0.5175 | −0.1918 | 0.029* | |
H14D | −0.6268 | −0.4355 | −0.2710 | 0.029* | |
H14E | −0.5500 | −0.3464 | −0.1719 | 0.029* | |
C15A | 0.2445 (4) | 0.1965 (3) | −0.1369 (2) | 0.0147 (6) | |
O15A | 0.1286 (3) | 0.2523 (3) | −0.19137 (16) | 0.0221 (5) | |
O16A | 0.4266 (3) | 0.2772 (3) | −0.11217 (16) | 0.0191 (5) | |
N1B | 0.0615 (3) | 0.2061 (3) | 0.32343 (18) | 0.0159 (5) | |
C2B | 0.1870 (5) | 0.1993 (4) | 0.2452 (2) | 0.0180 (6) | |
O2B | 0.1130 (3) | 0.1086 (3) | 0.16897 (16) | 0.0213 (5) | |
N3B | 0.3857 (4) | 0.2934 (3) | 0.25610 (19) | 0.0177 (5) | |
C4B | 0.4595 (4) | 0.3876 (3) | 0.3405 (2) | 0.0170 (6) | |
N4B | 0.6565 (4) | 0.4730 (3) | 0.3486 (2) | 0.0217 (6) | |
H4B1 | 0.7336 | 0.4663 | 0.2993 | 0.026* | |
H4B2 | 0.7092 | 0.5360 | 0.4032 | 0.026* | |
C5B | 0.3341 (4) | 0.3999 (3) | 0.4196 (2) | 0.0165 (6) | |
H5B | 0.3865 | 0.4694 | 0.4785 | 0.020* | |
C6B | 0.1384 (5) | 0.3083 (4) | 0.4070 (2) | 0.0180 (6) | |
H6B | 0.0503 | 0.3149 | 0.4580 | 0.022* | |
C7B | −0.1512 (4) | 0.1027 (4) | 0.3154 (2) | 0.0189 (6) | |
H7B1 | −0.2115 | 0.1133 | 0.2471 | 0.023* | |
H7B2 | −0.2258 | 0.1460 | 0.3653 | 0.023* | |
C8B | −0.1764 (4) | −0.0837 (4) | 0.3339 (2) | 0.0198 (6) | |
H8B1 | −0.3225 | −0.1467 | 0.3304 | 0.024* | |
H8B2 | −0.1140 | −0.1302 | 0.2798 | 0.024* | |
C9B | −0.0800 (4) | −0.1095 (3) | 0.4358 (2) | 0.0157 (6) | |
O9B | −0.1265 (3) | −0.0526 (3) | 0.51510 (17) | 0.0234 (5) | |
N10B | 0.0548 (3) | −0.1943 (3) | 0.43226 (18) | 0.0157 (5) | |
H10C | 0.0758 | −0.2270 | 0.3715 | 0.019* | |
C10B | 0.1732 (4) | −0.2406 (3) | 0.5166 (2) | 0.0155 (6) | |
H10D | 0.2900 | −0.2649 | 0.4856 | 0.019* | |
C11B | 0.2672 (4) | −0.0993 (3) | 0.5952 (2) | 0.0183 (6) | |
H11C | 0.1580 | −0.0676 | 0.6274 | 0.022* | |
H11D | 0.3453 | −0.1407 | 0.6484 | 0.022* | |
C12B | 0.4060 (4) | 0.0557 (4) | 0.5494 (2) | 0.0202 (6) | |
H12C | 0.3302 | 0.0921 | 0.4929 | 0.024* | |
H12D | 0.5204 | 0.0257 | 0.5214 | 0.024* | |
C13B | 0.4895 (4) | 0.2027 (4) | 0.6267 (2) | 0.0233 (6) | |
H13C | 0.5436 | 0.3079 | 0.5899 | 0.028* | |
H13D | 0.3768 | 0.2157 | 0.6652 | 0.028* | |
C14B | 0.6553 (4) | 0.1815 (4) | 0.7010 (2) | 0.0192 (6) | |
H14F | 0.6763 | 0.2642 | 0.7583 | 0.023* | |
H14G | 0.6124 | 0.0668 | 0.7284 | 0.023* | |
N14B | 0.8501 (4) | 0.2071 (3) | 0.6516 (2) | 0.0205 (5) | |
H14H | 0.8360 | 0.1220 | 0.6051 | 0.031* | |
H14I | 0.9502 | 0.2071 | 0.6994 | 0.031* | |
H14J | 0.8825 | 0.3077 | 0.6204 | 0.031* | |
C15B | 0.0597 (5) | −0.4054 (4) | 0.5669 (2) | 0.0208 (7) | |
O15B | 0.1675 (4) | −0.4642 (3) | 0.62742 (17) | 0.0282 (5) | |
O16B | −0.1228 (3) | −0.4744 (3) | 0.54323 (17) | 0.0242 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0149 (13) | 0.0147 (12) | 0.0183 (13) | 0.0031 (9) | 0.0004 (10) | 0.0017 (10) |
C2A | 0.0187 (15) | 0.0156 (14) | 0.0132 (14) | 0.0074 (12) | 0.0014 (12) | 0.0016 (11) |
O2A | 0.0207 (11) | 0.0250 (11) | 0.0178 (11) | 0.0053 (9) | 0.0009 (9) | −0.0037 (9) |
N3A | 0.0183 (12) | 0.0165 (12) | 0.0169 (12) | 0.0031 (10) | 0.0018 (10) | 0.0003 (9) |
C4A | 0.0204 (15) | 0.0149 (14) | 0.0151 (15) | 0.0070 (11) | −0.0002 (12) | 0.0042 (11) |
N4A | 0.0201 (13) | 0.0237 (13) | 0.0145 (13) | 0.0027 (10) | 0.0004 (10) | −0.0012 (10) |
C5A | 0.0257 (16) | 0.0143 (14) | 0.0152 (15) | 0.0053 (12) | 0.0006 (12) | −0.0005 (11) |
C6A | 0.0273 (16) | 0.0131 (13) | 0.0161 (15) | 0.0082 (12) | 0.0058 (12) | 0.0005 (11) |
C7A | 0.0154 (15) | 0.0200 (15) | 0.0225 (16) | 0.0056 (12) | 0.0025 (12) | 0.0022 (12) |
C8A | 0.0167 (14) | 0.0208 (14) | 0.0143 (14) | 0.0045 (11) | −0.0013 (11) | 0.0014 (11) |
C9A | 0.0129 (14) | 0.0131 (13) | 0.0197 (15) | 0.0004 (11) | 0.0028 (12) | −0.0003 (11) |
O9A | 0.0264 (12) | 0.0267 (11) | 0.0211 (11) | 0.0158 (9) | 0.0017 (9) | −0.0027 (9) |
N10A | 0.0167 (12) | 0.0132 (11) | 0.0129 (12) | 0.0042 (9) | −0.0014 (9) | −0.0022 (9) |
C10A | 0.0150 (13) | 0.0154 (13) | 0.0169 (14) | 0.0045 (11) | 0.0020 (11) | 0.0009 (10) |
C11A | 0.0141 (13) | 0.0178 (13) | 0.0234 (14) | 0.0051 (10) | −0.0016 (10) | −0.0023 (11) |
C12A | 0.0121 (13) | 0.0202 (14) | 0.0235 (15) | 0.0027 (11) | 0.0010 (11) | 0.0011 (11) |
C13A | 0.0178 (14) | 0.0183 (14) | 0.0364 (17) | 0.0046 (11) | 0.0013 (12) | −0.0044 (13) |
C14A | 0.0204 (14) | 0.0168 (14) | 0.0243 (15) | −0.0001 (11) | 0.0041 (12) | −0.0030 (12) |
N14A | 0.0206 (13) | 0.0188 (13) | 0.0181 (13) | 0.0061 (10) | 0.0001 (10) | −0.0003 (10) |
C15A | 0.0174 (14) | 0.0164 (13) | 0.0095 (13) | 0.0037 (11) | 0.0011 (11) | −0.0033 (11) |
O15A | 0.0205 (11) | 0.0222 (11) | 0.0225 (12) | 0.0056 (9) | −0.0038 (9) | 0.0047 (9) |
O16A | 0.0156 (10) | 0.0198 (10) | 0.0198 (11) | 0.0018 (8) | 0.0007 (8) | 0.0028 (8) |
N1B | 0.0157 (12) | 0.0171 (12) | 0.0154 (13) | 0.0053 (10) | 0.0021 (10) | 0.0007 (10) |
C2B | 0.0226 (15) | 0.0177 (14) | 0.0163 (15) | 0.0099 (12) | 0.0008 (12) | 0.0034 (12) |
O2B | 0.0204 (11) | 0.0253 (11) | 0.0167 (11) | 0.0054 (9) | −0.0013 (9) | −0.0053 (9) |
N3B | 0.0157 (12) | 0.0201 (13) | 0.0167 (13) | 0.0044 (10) | 0.0016 (10) | 0.0021 (10) |
C4B | 0.0177 (14) | 0.0145 (14) | 0.0195 (15) | 0.0063 (11) | −0.0004 (12) | 0.0022 (11) |
N4B | 0.0177 (13) | 0.0242 (13) | 0.0195 (14) | 0.0007 (10) | 0.0029 (11) | −0.0042 (11) |
C5B | 0.0217 (15) | 0.0133 (14) | 0.0142 (14) | 0.0052 (12) | −0.0008 (12) | −0.0007 (11) |
C6B | 0.0212 (15) | 0.0169 (14) | 0.0182 (16) | 0.0089 (11) | 0.0028 (12) | 0.0024 (11) |
C7B | 0.0160 (15) | 0.0221 (15) | 0.0189 (16) | 0.0065 (12) | −0.0001 (12) | 0.0028 (12) |
C8B | 0.0153 (14) | 0.0196 (15) | 0.0219 (16) | 0.0022 (12) | −0.0030 (12) | −0.0012 (12) |
C9B | 0.0151 (14) | 0.0117 (13) | 0.0176 (15) | 0.0000 (11) | 0.0001 (12) | −0.0003 (11) |
O9B | 0.0257 (12) | 0.0265 (11) | 0.0207 (11) | 0.0118 (9) | 0.0026 (9) | −0.0023 (9) |
N10B | 0.0181 (13) | 0.0158 (12) | 0.0126 (12) | 0.0038 (9) | 0.0019 (10) | 0.0009 (9) |
C10B | 0.0140 (13) | 0.0169 (13) | 0.0155 (14) | 0.0045 (11) | 0.0001 (11) | 0.0001 (11) |
C11B | 0.0197 (13) | 0.0152 (13) | 0.0172 (13) | 0.0018 (11) | −0.0032 (10) | −0.0001 (10) |
C12B | 0.0181 (14) | 0.0193 (14) | 0.0216 (15) | 0.0034 (11) | −0.0001 (11) | 0.0038 (12) |
C13B | 0.0234 (15) | 0.0188 (14) | 0.0258 (15) | 0.0043 (12) | −0.0023 (12) | 0.0023 (12) |
C14B | 0.0172 (14) | 0.0183 (14) | 0.0194 (14) | 0.0010 (11) | 0.0012 (11) | 0.0007 (11) |
N14B | 0.0205 (13) | 0.0181 (12) | 0.0211 (13) | 0.0025 (10) | 0.0025 (10) | −0.0002 (10) |
C15B | 0.0274 (17) | 0.0167 (14) | 0.0171 (15) | 0.0046 (13) | 0.0031 (13) | −0.0031 (12) |
O15B | 0.0371 (14) | 0.0206 (11) | 0.0233 (13) | 0.0046 (10) | −0.0075 (11) | 0.0042 (9) |
O16B | 0.0221 (12) | 0.0228 (11) | 0.0228 (12) | −0.0010 (9) | 0.0028 (9) | 0.0004 (9) |
N1A—C6A | 1.364 (4) | N1B—C6B | 1.365 (4) |
N1A—C2A | 1.402 (4) | N1B—C2B | 1.403 (4) |
N1A—C7A | 1.471 (4) | N1B—C7B | 1.466 (4) |
C2A—O2A | 1.236 (4) | C2B—O2B | 1.240 (4) |
C2A—N3A | 1.344 (4) | C2B—N3B | 1.364 (4) |
N3A—C4A | 1.347 (4) | N3B—C4B | 1.338 (4) |
C4A—N4A | 1.326 (4) | C4B—N4B | 1.336 (4) |
C4A—C5A | 1.427 (4) | C4B—C5B | 1.424 (4) |
N4A—H4A1 | 0.8800 | N4B—H4B1 | 0.8800 |
N4A—H4A2 | 0.8800 | N4B—H4B2 | 0.8800 |
C5A—C6A | 1.343 (4) | C5B—C6B | 1.343 (4) |
C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
C6A—H6A | 0.9500 | C6B—H6B | 0.9500 |
C7A—C8A | 1.530 (4) | C7B—C8B | 1.529 (4) |
C7A—H7A1 | 0.9900 | C7B—H7B1 | 0.9900 |
C7A—H7A2 | 0.9900 | C7B—H7B2 | 0.9900 |
C8A—C9A | 1.522 (4) | C8B—C9B | 1.515 (4) |
C8A—H8A1 | 0.9900 | C8B—H8B1 | 0.9900 |
C8A—H8A2 | 0.9900 | C8B—H8B2 | 0.9900 |
C9A—O9A | 1.234 (4) | C9B—O9B | 1.245 (3) |
C9A—N10A | 1.336 (4) | C9B—N10B | 1.329 (4) |
N10A—C10A | 1.456 (4) | N10B—C10B | 1.468 (4) |
N10A—H10A | 0.8800 | N10B—H10C | 0.8800 |
C10A—C11A | 1.529 (4) | C10B—C11B | 1.521 (4) |
C10A—C15A | 1.542 (4) | C10B—C15B | 1.544 (4) |
C10A—H10B | 1.0000 | C10B—H10D | 1.0000 |
C11A—C12A | 1.529 (4) | C11B—C12B | 1.518 (4) |
C11A—H11A | 0.9900 | C11B—H11C | 0.9900 |
C11A—H11B | 0.9900 | C11B—H11D | 0.9900 |
C12A—C13A | 1.531 (4) | C12B—C13B | 1.531 (4) |
C12A—H12A | 0.9900 | C12B—H12C | 0.9900 |
C12A—H12B | 0.9900 | C12B—H12D | 0.9900 |
C13A—C14A | 1.517 (4) | C13B—C14B | 1.519 (4) |
C13A—H13A | 0.9900 | C13B—H13C | 0.9900 |
C13A—H13B | 0.9900 | C13B—H13D | 0.9900 |
C14A—N14A | 1.490 (4) | C14B—N14B | 1.496 (4) |
C14A—H14A | 0.9900 | C14B—H14F | 0.9900 |
C14A—H14B | 0.9900 | C14B—H14G | 0.9900 |
N14A—H14C | 0.9100 | N14B—H14H | 0.9100 |
N14A—H14D | 0.9100 | N14B—H14I | 0.9100 |
N14A—H14E | 0.9100 | N14B—H14J | 0.9100 |
C15A—O15A | 1.241 (4) | C15B—O16B | 1.242 (4) |
C15A—O16A | 1.261 (3) | C15B—O15B | 1.262 (4) |
C6A—N1A—C2A | 120.6 (2) | C6B—N1B—C2B | 119.9 (2) |
C6A—N1A—C7A | 120.7 (2) | C6B—N1B—C7B | 120.2 (2) |
C2A—N1A—C7A | 118.8 (2) | C2B—N1B—C7B | 119.9 (2) |
O2A—C2A—N3A | 123.3 (3) | O2B—C2B—N3B | 122.5 (3) |
O2A—C2A—N1A | 117.9 (2) | O2B—C2B—N1B | 118.8 (3) |
N3A—C2A—N1A | 118.8 (2) | N3B—C2B—N1B | 118.6 (3) |
C4A—N3A—C2A | 120.8 (2) | C4B—N3B—C2B | 120.4 (2) |
N4A—C4A—N3A | 118.8 (3) | N4B—C4B—N3B | 118.0 (3) |
N4A—C4A—C5A | 120.1 (3) | N4B—C4B—C5B | 120.1 (3) |
N3A—C4A—C5A | 121.0 (3) | N3B—C4B—C5B | 121.9 (3) |
C4A—N4A—H4A1 | 120.0 | C4B—N4B—H4B1 | 120.0 |
C4A—N4A—H4A2 | 120.0 | C4B—N4B—H4B2 | 120.0 |
H4A1—N4A—H4A2 | 120.0 | H4B1—N4B—H4B2 | 120.0 |
C6A—C5A—C4A | 117.6 (3) | C6B—C5B—C4B | 116.8 (3) |
C6A—C5A—H5A | 121.2 | C6B—C5B—H5B | 121.6 |
C4A—C5A—H5A | 121.2 | C4B—C5B—H5B | 121.6 |
C5A—C6A—N1A | 121.2 (3) | C5B—C6B—N1B | 122.3 (3) |
C5A—C6A—H6A | 119.4 | C5B—C6B—H6B | 118.9 |
N1A—C6A—H6A | 119.4 | N1B—C6B—H6B | 118.9 |
N1A—C7A—C8A | 112.0 (2) | N1B—C7B—C8B | 112.5 (2) |
N1A—C7A—H7A1 | 109.2 | N1B—C7B—H7B1 | 109.1 |
C8A—C7A—H7A1 | 109.2 | C8B—C7B—H7B1 | 109.1 |
N1A—C7A—H7A2 | 109.2 | N1B—C7B—H7B2 | 109.1 |
C8A—C7A—H7A2 | 109.2 | C8B—C7B—H7B2 | 109.1 |
H7A1—C7A—H7A2 | 107.9 | H7B1—C7B—H7B2 | 107.8 |
C9A—C8A—C7A | 111.4 (2) | C9B—C8B—C7B | 112.2 (2) |
C9A—C8A—H8A1 | 109.3 | C9B—C8B—H8B1 | 109.2 |
C7A—C8A—H8A1 | 109.3 | C7B—C8B—H8B1 | 109.2 |
C9A—C8A—H8A2 | 109.3 | C9B—C8B—H8B2 | 109.2 |
C7A—C8A—H8A2 | 109.3 | C7B—C8B—H8B2 | 109.2 |
H8A1—C8A—H8A2 | 108.0 | H8B1—C8B—H8B2 | 107.9 |
O9A—C9A—N10A | 122.4 (3) | O9B—C9B—N10B | 124.2 (3) |
O9A—C9A—C8A | 121.0 (3) | O9B—C9B—C8B | 120.8 (3) |
N10A—C9A—C8A | 116.5 (2) | N10B—C9B—C8B | 115.0 (3) |
C9A—N10A—C10A | 121.5 (2) | C9B—N10B—C10B | 128.4 (2) |
C9A—N10A—H10A | 119.2 | C9B—N10B—H10C | 115.8 |
C10A—N10A—H10A | 119.2 | C10B—N10B—H10C | 115.8 |
N10A—C10A—C11A | 109.4 (2) | N10B—C10B—C11B | 114.5 (2) |
N10A—C10A—C15A | 112.1 (2) | N10B—C10B—C15B | 113.7 (2) |
C11A—C10A—C15A | 114.9 (2) | C11B—C10B—C15B | 111.2 (2) |
N10A—C10A—H10B | 106.6 | N10B—C10B—H10D | 105.5 |
C11A—C10A—H10B | 106.6 | C11B—C10B—H10D | 105.5 |
C15A—C10A—H10B | 106.6 | C15B—C10B—H10D | 105.5 |
C10A—C11A—C12A | 112.1 (2) | C12B—C11B—C10B | 112.2 (2) |
C10A—C11A—H11A | 109.2 | C12B—C11B—H11C | 109.2 |
C12A—C11A—H11A | 109.2 | C10B—C11B—H11C | 109.2 |
C10A—C11A—H11B | 109.2 | C12B—C11B—H11D | 109.2 |
C12A—C11A—H11B | 109.2 | C10B—C11B—H11D | 109.2 |
H11A—C11A—H11B | 107.9 | H11C—C11B—H11D | 107.9 |
C13A—C12A—C11A | 114.6 (2) | C11B—C12B—C13B | 112.5 (2) |
C13A—C12A—H12A | 108.6 | C11B—C12B—H12C | 109.1 |
C11A—C12A—H12A | 108.6 | C13B—C12B—H12C | 109.1 |
C13A—C12A—H12B | 108.6 | C11B—C12B—H12D | 109.1 |
C11A—C12A—H12B | 108.6 | C13B—C12B—H12D | 109.1 |
H12A—C12A—H12B | 107.6 | H12C—C12B—H12D | 107.8 |
C14A—C13A—C12A | 115.5 (2) | C14B—C13B—C12B | 114.2 (2) |
C14A—C13A—H13A | 108.4 | C14B—C13B—H13C | 108.7 |
C12A—C13A—H13A | 108.4 | C12B—C13B—H13C | 108.7 |
C14A—C13A—H13B | 108.4 | C14B—C13B—H13D | 108.7 |
C12A—C13A—H13B | 108.4 | C12B—C13B—H13D | 108.7 |
H13A—C13A—H13B | 107.5 | H13C—C13B—H13D | 107.6 |
N14A—C14A—C13A | 112.0 (3) | N14B—C14B—C13B | 111.4 (2) |
N14A—C14A—H14A | 109.2 | N14B—C14B—H14F | 109.3 |
C13A—C14A—H14A | 109.2 | C13B—C14B—H14F | 109.3 |
N14A—C14A—H14B | 109.2 | N14B—C14B—H14G | 109.3 |
C13A—C14A—H14B | 109.2 | C13B—C14B—H14G | 109.3 |
H14A—C14A—H14B | 107.9 | H14F—C14B—H14G | 108.0 |
C14A—N14A—H14C | 109.5 | C14B—N14B—H14H | 109.5 |
C14A—N14A—H14D | 109.5 | C14B—N14B—H14I | 109.5 |
H14C—N14A—H14D | 109.5 | H14H—N14B—H14I | 109.5 |
C14A—N14A—H14E | 109.5 | C14B—N14B—H14J | 109.5 |
H14C—N14A—H14E | 109.5 | H14H—N14B—H14J | 109.5 |
H14D—N14A—H14E | 109.5 | H14I—N14B—H14J | 109.5 |
O15A—C15A—O16A | 124.1 (3) | O16B—C15B—O15B | 124.7 (3) |
O15A—C15A—C10A | 117.9 (2) | O16B—C15B—C10B | 120.0 (3) |
O16A—C15A—C10A | 117.9 (3) | O15B—C15B—C10B | 115.2 (3) |
C6A—N1A—C2A—O2A | −179.8 (3) | C6B—N1B—C2B—O2B | −178.4 (3) |
C7A—N1A—C2A—O2A | −0.2 (4) | C7B—N1B—C2B—O2B | 2.0 (4) |
C6A—N1A—C2A—N3A | −0.7 (4) | C6B—N1B—C2B—N3B | 1.5 (4) |
C7A—N1A—C2A—N3A | 179.0 (3) | C7B—N1B—C2B—N3B | −178.2 (2) |
O2A—C2A—N3A—C4A | 177.4 (3) | O2B—C2B—N3B—C4B | −179.0 (3) |
N1A—C2A—N3A—C4A | −1.7 (4) | N1B—C2B—N3B—C4B | 1.1 (4) |
C2A—N3A—C4A—N4A | −178.6 (3) | C2B—N3B—C4B—N4B | 177.9 (2) |
C2A—N3A—C4A—C5A | 2.5 (4) | C2B—N3B—C4B—C5B | −2.8 (4) |
N4A—C4A—C5A—C6A | −179.8 (3) | N4B—C4B—C5B—C6B | −178.9 (3) |
N3A—C4A—C5A—C6A | −0.9 (4) | N3B—C4B—C5B—C6B | 1.8 (4) |
C4A—C5A—C6A—N1A | −1.5 (4) | C4B—C5B—C6B—N1B | 0.9 (4) |
C2A—N1A—C6A—C5A | 2.3 (4) | C2B—N1B—C6B—C5B | −2.5 (4) |
C7A—N1A—C6A—C5A | −177.3 (3) | C7B—N1B—C6B—C5B | 177.1 (3) |
C6A—N1A—C7A—C8A | 102.4 (3) | C6B—N1B—C7B—C8B | −104.6 (3) |
C2A—N1A—C7A—C8A | −77.2 (3) | C2B—N1B—C7B—C8B | 75.1 (3) |
N1A—C7A—C8A—C9A | −57.6 (3) | N1B—C7B—C8B—C9B | 56.5 (3) |
C7A—C8A—C9A—O9A | −46.2 (4) | C7B—C8B—C9B—O9B | 54.9 (4) |
C7A—C8A—C9A—N10A | 133.1 (3) | C7B—C8B—C9B—N10B | −124.6 (3) |
O9A—C9A—N10A—C10A | 2.8 (4) | O9B—C9B—N10B—C10B | 0.8 (4) |
C8A—C9A—N10A—C10A | −176.5 (2) | C8B—C9B—N10B—C10B | −179.7 (2) |
C9A—N10A—C10A—C11A | 117.0 (3) | C9B—N10B—C10B—C11B | −44.8 (4) |
C9A—N10A—C10A—C15A | −114.4 (3) | C9B—N10B—C10B—C15B | 84.7 (3) |
N10A—C10A—C11A—C12A | −67.0 (3) | N10B—C10B—C11B—C12B | −58.1 (3) |
C15A—C10A—C11A—C12A | 165.9 (2) | C15B—C10B—C11B—C12B | 171.3 (2) |
C10A—C11A—C12A—C13A | −77.3 (3) | C10B—C11B—C12B—C13B | 176.0 (2) |
C11A—C12A—C13A—C14A | −72.9 (3) | C11B—C12B—C13B—C14B | 75.1 (3) |
C12A—C13A—C14A—N14A | −62.3 (3) | C12B—C13B—C14B—N14B | 73.6 (3) |
N10A—C10A—C15A—O15A | −153.2 (2) | N10B—C10B—C15B—O16B | −8.4 (4) |
C11A—C10A—C15A—O15A | −27.5 (4) | C11B—C10B—C15B—O16B | 122.6 (3) |
N10A—C10A—C15A—O16A | 30.2 (3) | N10B—C10B—C15B—O15B | 168.4 (2) |
C11A—C10A—C15A—O16A | 155.9 (2) | C11B—C10B—C15B—O15B | −60.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4A—H4A1···N3Bi | 0.88 | 2.08 | 2.956 (4) | 173 |
N4A—H4A2···O16Ai | 0.88 | 2.14 | 2.857 (3) | 138 |
N10A—H10A···O2B | 0.88 | 2.06 | 2.907 (3) | 161 |
N14A—H14D···O15Bii | 0.91 | 1.86 | 2.769 (4) | 177 |
N14A—H14E···O9Aiii | 0.91 | 1.88 | 2.787 (4) | 176 |
N14A—H14C···O16Ai | 0.91 | 1.97 | 2.870 (4) | 168 |
N14A—H14C···O15Ai | 0.91 | 2.56 | 3.095 (3) | 118 |
N4B—H4B1···N3Aiv | 0.88 | 2.07 | 2.939 (4) | 171 |
N4B—H4B2···O16Biv | 0.88 | 2.15 | 2.876 (3) | 140 |
N10B—H10C···O2A | 0.88 | 1.95 | 2.796 (3) | 161 |
N14B—H14I···O15Av | 0.91 | 1.80 | 2.694 (3) | 165 |
N14B—H14H···O9Bvi | 0.91 | 1.95 | 2.842 (4) | 166 |
N14B—H14J···O15Biv | 0.91 | 2.29 | 2.988 (3) | 133 |
N14B—H14J···O16Biv | 0.91 | 2.10 | 2.987 (4) | 165 |
Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y, z−1; (iii) x−1, y, z; (iv) x+1, y+1, z; (v) x+1, y, z+1; (vi) x+1, y, z. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C16H18N4O4 | C10H14N4O5·H2O | C13H21N5O4 |
Mr | 330.34 | 288.27 | 311.35 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 100 | 100 | 100 |
a, b, c (Å) | 9.3587 (12), 10.3445 (13), 16.925 (2) | 4.863 (1), 10.771 (2), 12.228 (2) | 6.9334 (9), 8.2977 (10), 13.2491 (16) |
α, β, γ (°) | 92.079 (2), 95.775 (2), 95.245 (2) | 80.45 (3), 89.23 (3), 88.61 (3) | 90.780 (2), 93.498 (2), 107.293 (2) |
V (Å3) | 1621.7 (4) | 631.4 (2) | 726.02 (16) |
Z | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.13 | 0.11 |
Crystal size (mm) | 0.25 × 0.20 × 0.04 | 0.25 × 0.25 × 0.06 | 0.40 × 0.18 × 0.04 |
Data collection | |||
Diffractometer | Bruker SMART APEX diffractometer | Bruker SMART APEX diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.832, 0.998 | 0.827, 0.993 | 0.878, 0.996 |
No. of measured, independent and observed reflections | 8913, 6059, 5788 [I > \2s(I)] | 3919, 2336, 2284 [I > 2σ(I)] | 7954, 2970, 2714 [I > 2σ(I)] |
Rint | 0.025 | 0.022 | 0.025 |
(sin θ/λ)max (Å−1) | 0.610 | 0.610 | 0.625 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.150, 1.13 | 0.048, 0.114, 1.17 | 0.038, 0.100, 1.00 |
No. of reflections | 6059 | 2336 | 2970 |
No. of parameters | 896 | 377 | 399 |
No. of restraints | 180 | 3 | 3 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.31 | 0.32, −0.25 | 0.34, −0.19 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1998), SHELXD (Sheldrick, 1990b), SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), Mercury (Bruno et al., 2002).
C2A—N1A—C7A—C8A | −74.4 (5) | C2C—N1C—C7C—C8C | −78.4 (5) |
N1A—C7A—C8A—C9A | −66.3 (5) | N1C—C7C—C8C—C9C | −61.1 (5) |
C7A—C8A—C9A—N10A | 150.0 (4) | C7C—C8C—C9C—N10C | 124.4 (5) |
C8A—C9A—N10A—C10A | −178.8 (4) | C8C—C9C—N10C—C10C | 179.2 (4) |
C9A—N10A—C10A—C11A | 135.4 (5) | C9C—N10C—C10C—C11C | 164.5 (4) |
N10A—C10A—C11A—C12A | −53.9 (6) | N10C—C10C—C11C—C12C | −71.6 (5) |
C10A—C11A—C12A—C13A | −47.3 (8) | C10C—C11C—C12C—C13C | 92.9 (4) |
C2B—N1B—C7B—C8B | −78.4 (5) | C2D—N1D—C7D—C8D | −80.6 (5) |
N1B—C7B—C8B—C9B | −61.7 (5) | N1D—C7D—C8D—C9D | −64.2 (5) |
C7B—C8B—C9B—N10B | 148.0 (4) | C7D—C8D—C9D—N10D | 124.2 (4) |
C8B—C9B—N10B—C10B | 179.9 (4) | C8D—C9D—N10D—C10D | 178.4 (4) |
C9B—N10B—C10B—C11B | 141.4 (5) | C9D—N10D—C10D—C11D | 163.8 (4) |
N10B—C10B—C11B—C12B | −63.7 (6) | N10D—C10D—C11D—C12D | −59.8 (6) |
C10B—C11B—C12B—C13B | −24.7 (7) | C10D—C11D—C12D—C13D | 99.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O18Di | 0.88 | 1.75 | 2.623 (6) | 171 |
N4A—H4AA···O19Di | 0.88 | 1.94 | 2.811 (7) | 173 |
N10A—H10A···O19Cii | 0.88 | 2.19 | 3.036 (6) | 161 |
N3B—H3B···O18Ciii | 0.88 | 1.73 | 2.565 (6) | 159 |
N4B—H4AB···O19Ciii | 0.88 | 2.14 | 2.965 (7) | 156 |
N4B—H4BB···O2Aiv | 0.88 | 2.42 | 2.934 (7) | 118 |
N10B—H10B···O19Di | 0.88 | 2.05 | 2.885 (6) | 159 |
N3C—H3C···O19B | 0.88 | 1.74 | 2.601 (5) | 167 |
N4C—H4AC···O18B | 0.88 | 2.05 | 2.903 (6) | 164 |
N4C—H4BC···O19Av | 0.88 | 2.28 | 3.090 (7) | 154 |
N10C—H10C···O18Avi | 0.88 | 2.03 | 2.890 (5) | 167 |
N3D—H3D···O19Avi | 0.88 | 1.75 | 2.615 (5) | 168 |
N4D—H4AD···O18Avi | 0.88 | 2.06 | 2.920 (6) | 165 |
N4D—H4BD···O19B | 0.88 | 2.23 | 3.047 (6) | 155 |
N10D—H10D···O18Biv | 0.88 | 2.10 | 2.945 (5) | 162 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z−1; (iii) x+1, y, z−1; (iv) x, y−1, z; (v) x−1, y, z+1; (vi) x−1, y−1, z+1. |
C2A—N1A—C7A—C8A | 74.2 (4) | C2B—N1B—C7B—C8B | −80.8 (4) |
N1A—C7A—C8A—C9A | −178.1 (3) | N1B—C7B—C8B—C9B | −179.9 (3) |
C7A—C8A—C9A—N10A | 159.2 (3) | C7B—C8B—C9B—N10B | −160.2 (4) |
C8A—C9A—N10A—C10A | 177.3 (3) | C8B—C9B—N10B—C10B | −179.8 (3) |
C9A—N10A—C10A—C11A | 157.7 (4) | C9B—N10B—C10B—C11B | −67.9 (5) |
N10A—C10A—C11A—O11A | −62.5 (5) | N10B—C10B—C11B—O11B | −59.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O13Ai | 0.88 | 1.88 | 2.747 (4) | 167 |
N4A—H4AA···O12Ai | 0.88 | 1.93 | 2.805 (5) | 170 |
N4A—H4BA···O13Bii | 0.88 | 2.06 | 2.928 (5) | 168 |
N10A—H10A···O9Aiii | 0.88 | 2.12 | 2.975 (5) | 163 |
O11A—H11A···O12B | 0.84 | 1.93 | 2.704 (5) | 153 |
N3B—H3B···O13Biv | 0.88 | 1.89 | 2.759 (4) | 168 |
N4B—H4AB···O12Biv | 0.88 | 1.91 | 2.789 (5) | 174 |
N4B—H4BB···O13Av | 0.88 | 2.08 | 2.960 (5) | 175 |
N10B—H10B···O9Bvi | 0.88 | 2.20 | 3.000 (5) | 150 |
O11B—H11B···O12Avii | 0.84 | 2.01 | 2.759 (4) | 148 |
O1C—H1C···O11Avi | 0.93 (5) | 1.96 (6) | 2.841 (5) | 159 (5) |
O1C—H2C···O9A | 0.88 (6) | 2.07 (6) | 2.909 (4) | 158 (6) |
O1D—H1D···O11B | 0.91 (8) | 2.05 (8) | 2.851 (5) | 146 (7) |
O1D—H2D···O9Bvi | 0.80 (7) | 2.17 (7) | 2.951 (4) | 164 (7) |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z−1; (iii) x+1, y, z; (iv) x−1, y−1, z; (v) x, y−1, z; (vi) x−1, y, z; (vii) x, y, z+1. |
C2A—N1A—C7A—C8A | −77.2 (3) | C2B—N1B—C7B—C8B | 75.1 (3) |
N1A—C7A—C8A—C9A | −57.6 (3) | N1B—C7B—C8B—C9B | 56.5 (3) |
C7A—C8A—C9A—N10A | 133.1 (3) | C7B—C8B—C9B—N10B | −124.6 (3) |
C8A—C9A—N10A—C10A | −176.5 (2) | C8B—C9B—N10B—C10B | −179.7 (2) |
C9A—N10A—C10A—C11A | 117.0 (3) | C9B—N10B—C10B—C11B | −44.8 (4) |
N10A—C10A—C11A—C12A | −67.0 (3) | N10B—C10B—C11B—C12B | −58.1 (3) |
C10A—C11A—C12A—C13A | −77.3 (3) | C10B—C11B—C12B—C13B | 176.0 (2) |
C11A—C12A—C13A—C14A | −72.9 (3) | C11B—C12B—C13B—C14B | 75.1 (3) |
C12A—C13A—C14A—N14A | −62.3 (3) | C12B—C13B—C14B—N14B | 73.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4A—H4A1···N3Bi | 0.88 | 2.08 | 2.956 (4) | 173 |
N4A—H4A2···O16Ai | 0.88 | 2.14 | 2.857 (3) | 138 |
N10A—H10A···O2B | 0.88 | 2.06 | 2.907 (3) | 161 |
N14A—H14D···O15Bii | 0.91 | 1.86 | 2.769 (4) | 177 |
N14A—H14E···O9Aiii | 0.91 | 1.88 | 2.787 (4) | 176 |
N14A—H14C···O16Ai | 0.91 | 1.97 | 2.870 (4) | 168 |
N14A—H14C···O15Ai | 0.91 | 2.56 | 3.095 (3) | 118 |
N4B—H4B1···N3Aiv | 0.88 | 2.07 | 2.939 (4) | 171 |
N4B—H4B2···O16Biv | 0.88 | 2.15 | 2.876 (3) | 140 |
N10B—H10C···O2A | 0.88 | 1.95 | 2.796 (3) | 161 |
N14B—H14I···O15Av | 0.91 | 1.80 | 2.694 (3) | 165 |
N14B—H14H···O9Bvi | 0.91 | 1.95 | 2.842 (4) | 166 |
N14B—H14J···O15Biv | 0.91 | 2.29 | 2.988 (3) | 133 |
N14B—H14J···O16Biv | 0.91 | 2.10 | 2.987 (4) | 165 |
Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y, z−1; (iii) x−1, y, z; (iv) x+1, y+1, z; (v) x+1, y, z+1; (vi) x+1, y, z. |
Compound | (I)1) | (II)1) | (III)1) | (IV) | (V) | (VI) | (VII) | (VIII) |
Amino acid | L-Phe | L-Ser | L-Lys | L-Tyr | L-Thr | L-Trp | L-Ile | L-Ala |
Position | O+ | S± | O± | O+ | 0± | S± | S– | 0± |
1) the present structures. |
Nucleic acid-incorporated peptides have been designed with the expectation that the incorporated amino acids could potentially strengthen interactions with complementary bases (Williams et al., 1977; Voet, 1980). We have focused on the cytosine base and designed hybrid peptides (Tarui et al., 1996). The cytosine-incorporated dipeptides have shown affinities for 7-methyl-9-ethylguanine (7 mG) but not for 9-ethylguanine (Asano et al., 2002). The incorporated amino acids affect the association constants between the dipeptides and 7 mG (0.2–6.6 × 10−6 M−1) and induce different binding phases at low and high peptide concentrations. To analyze the fundamental characteristics of cytosine hybrid dipeptides, the structures of the title compounds, (I)–(III), have been determined.
Four molecules of (I) are present in the asymmetric unit (molecules A–D), with similar folded conformations (Fig. 1). Slight disorder is observed for the phenyl ring of C, with approximately 4% occupancy for the minor site. No significant difference is observed for the carboxyl C18n—O18n and C18n—O19n bond lengths (n = A–D), and a zwitterion form with N3-quarternization is established for molecules A–D. Rotations about the C10n–C11n and C11n–C12n bonds mainly contribute to the different orientations between the pyrimidine and phenyl rings in the independent molecules (Table 1). The angles between the least-squares planes of the rings are 38.8 (2), 57.8 (2), 31.2 (3) and 27.8 (2)° for A, B, C (major part) and D, respectively, with intramolecular distances of, respectively, 4.401 (4), 4.683 (3), 4.392 (4) and 4.380 (3) Å between the centroids of the pyrimidine and phenyl rings, indicative of no intramolecular interaction between the aromatic rings. A similar folding was found in the structure of (2-carboxyethyl)-cytosine-1-yl-L-tyrosine, (IV) (Doi, Miyako et al., 1999). A complicated hydrogen-bonding scheme is observed for (I) (Table 2). Atoms N3n and N4n of the cytosine base interact with the carboxyl group atoms O18n and O19n (Fig. 2). These pairings form eight-membered rings between molecules A and D(x, y + 1, z), B and C(x + 1, y, z − 1), C and B, and D and A(x − 1, y − 1, z + 1), with r.m.s. deviations of 1/4, 0.23, 0.17 and 0.15 Å, respectively. Atoms N4n of molecules B, C and D are hydrogen bonded to two acceptor atoms, but atom N4A (molecule A) has one acceptor atom (O19D). Consequently, molecule A has three hydrogen-bond donors, and molecules B, C and D have four (Table 2). These differences are related to acceptor atoms, because the numbers of hydrogen-bond acceptor atoms are 5, 4, 3 and 3 for molecules A, B, C and D, respectively. The independent molecules having slightly different conformations form this unique hydrogen-bonding network with no solvent molecules.
The two independent molecules of (II) (A and B) crystallize in a monohydrate form with a extended conformation (Fig. 3). In molecules A and B, the rotations of the N1m—C7m bonds are inverse to one another [74.2 (4) and −80.8 (4)°, for m = A and B, respectively, in Table 3], and the dispositions of the L-Ser moieties are different for the base planes. The extended structures are induced by the trans positions of the C7m—C8m bond, viz. −178.1 (3) and −179.9 (3)° for A and B, respectively. The (2-carboxyethyl)-cytosine-1-yl-L-threonine (V) also crystallizes as a monohydrated form, but the syn position of the C7—C8 bond results in an L-figure conformation (N1—C7—C8—C9 = 112.5 (3) and 113.3 (3)°; Doi, Asano & Ishida, 1999). The structures of (II) are rather similar to the extended structures of (2-carboxyethyl)-cytosine-1-yl-L-tryptophan, (V) (N1—C7—C8—C9 = −175.4 (4) and −179.4 (4)°; Doi, Tarui et al., 1998). Hydrogen bonds between the cytosine base and the carboxyl group are formed between symmetry-related molecules A (N3A···O13Ai and N4A···O12Ai), indicating the zwitterion form; in addition the C12—O12 and C12—O13 bond lengths are similar (Fig. 3 and Table 4). Atom N4A also interacts with atom O13B of the adjacent molecule B. The hydroxy group of molecule A (O11A) interacts with the carboxyl group of molecule B (O12B) and a water molecule (O1C). Similar hydrogen-bonds are observed for symmetry-related molecules B. The water molecule O1C bridges two molecules A, which translate along (100) (as O9A···O1C···O11Avi), and the water molecule O1D similarly bridges molecules B (O9Bvi···O1D..·O11B; symmetry code as in Table 4).
Two independent molecules of (III) (A and B) are also present in the asymmetric unit, with a folded form (Fig. 5). Molecules A and B are related by pseudosymmetry that fits 95% of the atoms of both molecules, but they are distinguished by some bond rotations (Table 5); the rotations of the N1o–C7o bonds induce different foldings for the base plane, viz. −77.3 (2) and 75.1 (3)° for o = A and B, respectively. Moreover, the Lys side chains are expanded over the base planes in a similar manner in A and B. These conformations are also different at the terminal ε-amino groups; the C12—C13—C14—N14 torsion angles are −62.3 (3) and 73.6 (3)° for A and B, respectively. Cytosine–cytosine base pairings (N4A···N3B and N4B···N3A) are formed between molecules A and B (Table 6 and Fig. 6), a phenomenon that has not been observed in the structures of cytosine-hybrid dipeptides. This base pair indicates a unionized state of N3. The ε-amino groups (N14A and N14B) interact with carboxyl groups (Table 6), and ionized states are established for the carboxyl and ε-amino groups.
The independent molecules of each dipeptide have been fitted to the cytosine base (Fig. 7). The phenyl rings of (I) are located at one side of the cytosine base plane, but the side chains of (II) are separated from the base. The long side chains of (III) are located over the base, positioned on both sides of the base plane. When the positions of the amino acid side chain are defined as sites O and S, as shown in Fig. 7, the present and previously reported structures of cytosine-hybrid peptides are classified as listed in Table 7.
The side chains of (I), (III) and (IV) are located on site O, and the single folding to site O+ is observed for the aromatic analogues (I) and (IV). Compound (VI) also has an aromatic side chain, but the side chain position is S±. In (VI), intermolecular π–π interactions are observed between cytosine bases and indole rings (Doi, Tarui et al., 1998). This interaction seems to affect for the side-chain position of (IV). The side chains of (II) and (2-carboxyethyl)-cytosine-1-yl-L-isoleucine, (VII) (Doi, Tsunemichi et al., 1999), are folded to site S, but single folding to site S– is only observed for (VII). The side chains of (V) and (2-carboxyethyl)-cytosine-1-yl-L-alanine, (VIII) (Doi, Tarui et al., 1999) are expanded approximately perpendicular to the base plane (site 0±). We can postulate relations between these folding positions and the associate constants with 7 mG, but unfortunately find no clear pattern. However, the side chain position may be related to binding phases, because the two binding phases are observed for (I), (II), (IV), and (V). The hybrid dipeptides showing the two binding phases interact with 7 mG at the extra place(s) in addition to cytosine base. The hydroxyl groups of (II) and (V) separated from the cytosine base (sites S or 0) are suitable to interact with 7 mG molecules. The folding forms of (I) and (IV) have the space between the aromatic ring and base, which would accept a 7 mG molecule.