Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615008422/dk5035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615008422/dk5035Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615008422/dk5035sup3.pdf |
CCDC reference: 1062325
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C14H19N4O3·C4H3O4 | Z = 4 |
Mr = 406.40 | F(000) = 856 |
Triclinic, P1 | Dx = 1.409 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4700 (5) Å | Cell parameters from 6640 reflections |
b = 14.6637 (10) Å | θ = 3.0–28.8° |
c = 15.0285 (10) Å | µ = 0.11 mm−1 |
α = 61.535 (7)° | T = 293 K |
β = 83.550 (5)° | Prism, colourless |
γ = 71.020 (5)° | 0.4 × 0.3 × 0.15 mm |
V = 1915.6 (2) Å3 |
Xcalibur, Ruby, Gemini ultra diffractometer | 6752 independent reflections |
Radiation source: fine-focus sealed tube | 5223 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 5.1856 pixels mm-1 | θmax = 25.0°, θmin = 2.7° |
ω scans | h = −12→12 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −17→17 |
Tmin = 0.978, Tmax = 1.000 | l = −17→17 |
16621 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1954P] where P = (Fo2 + 2Fc2)/3 |
6752 reflections | (Δ/σ)max = 0.001 |
593 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C14H19N4O3·C4H3O4 | γ = 71.020 (5)° |
Mr = 406.40 | V = 1915.6 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.4700 (5) Å | Mo Kα radiation |
b = 14.6637 (10) Å | µ = 0.11 mm−1 |
c = 15.0285 (10) Å | T = 293 K |
α = 61.535 (7)° | 0.4 × 0.3 × 0.15 mm |
β = 83.550 (5)° |
Xcalibur, Ruby, Gemini ultra diffractometer | 6752 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 5223 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 1.000 | Rint = 0.028 |
16621 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.19 e Å−3 |
6752 reflections | Δρmin = −0.22 e Å−3 |
593 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 | ||
C1 | 0.61271 (15) | 0.38736 (12) | 0.11002 (12) | 0.0283 (4) | |
C2 | 0.72682 (16) | 0.29744 (13) | 0.10319 (13) | 0.0320 (4) | |
C3 | 0.85082 (16) | 0.29909 (13) | 0.08334 (13) | 0.0324 (4) | |
C4 | 0.96309 (16) | 0.20984 (13) | 0.07619 (13) | 0.0307 (4) | |
C5 | 0.11865 (16) | 0.88629 (12) | 0.11644 (13) | 0.0320 (4) | |
C6 | 0.23237 (17) | 0.79751 (13) | 0.10839 (14) | 0.0369 (4) | |
C7 | 0.35606 (16) | 0.79909 (13) | 0.08889 (13) | 0.0323 (4) | |
C8 | 0.46522 (16) | 0.71149 (13) | 0.07756 (13) | 0.0325 (4) | |
C9 | 0.15899 (16) | 0.40975 (13) | 0.11932 (12) | 0.0325 (4) | |
C11 | −0.03401 (16) | 0.49566 (13) | 0.17210 (12) | 0.0309 (4) | |
C12 | 0.03922 (16) | 0.53913 (12) | 0.20899 (12) | 0.0313 (4) | |
C13 | 0.17243 (17) | 0.51564 (13) | 0.19324 (13) | 0.0337 (4) | |
H13 | 0.2247 | 0.5429 | 0.2145 | 0.040* | |
C14 | −0.03083 (18) | 0.61316 (14) | 0.25435 (13) | 0.0394 (4) | |
H14A | −0.0914 | 0.6790 | 0.2022 | 0.047* | |
H14B | 0.0371 | 0.6342 | 0.2724 | 0.047* | |
C15 | −0.11169 (18) | 0.56891 (14) | 0.34698 (13) | 0.0370 (4) | |
C16 | −0.23083 (19) | 0.63986 (14) | 0.35654 (14) | 0.0428 (5) | |
H16 | −0.2647 | 0.7099 | 0.3032 | 0.051* | |
C17 | −0.30025 (19) | 0.60721 (15) | 0.44525 (15) | 0.0433 (5) | |
C18 | −0.25000 (19) | 0.50329 (15) | 0.52489 (14) | 0.0426 (5) | |
C19 | −0.13568 (19) | 0.42945 (14) | 0.51280 (14) | 0.0422 (4) | |
C20 | −0.06590 (19) | 0.46258 (14) | 0.42431 (13) | 0.0408 (4) | |
H20 | 0.0115 | 0.4134 | 0.4170 | 0.049* | |
C21 | −0.4828 (2) | 0.77353 (16) | 0.37748 (18) | 0.0679 (7) | |
H21A | −0.4262 | 0.8196 | 0.3566 | 0.102* | |
H21B | −0.5680 | 0.8081 | 0.3965 | 0.102* | |
H21C | −0.4977 | 0.7617 | 0.3225 | 0.102* | |
C22 | −0.4062 (3) | 0.4224 (2) | 0.63259 (19) | 0.0896 (9) | |
H22A | −0.4829 | 0.4717 | 0.5862 | 0.134* | |
H22B | −0.4346 | 0.3992 | 0.7009 | 0.134* | |
H22C | −0.3673 | 0.3600 | 0.6214 | 0.134* | |
C23 | 0.0037 (3) | 0.24246 (17) | 0.58657 (18) | 0.0744 (7) | |
H23A | −0.0153 | 0.2361 | 0.5291 | 0.112* | |
H23B | 0.0106 | 0.1751 | 0.6472 | 0.112* | |
H23C | 0.0876 | 0.2584 | 0.5785 | 0.112* | |
C31 | 0.66032 (16) | 0.92351 (12) | 0.10837 (12) | 0.0311 (4) | |
C33 | 0.47925 (16) | 1.00526 (12) | 0.17511 (12) | 0.0303 (4) | |
C34 | 0.56370 (16) | 1.03973 (12) | 0.21362 (12) | 0.0298 (4) | |
C35 | 0.69486 (16) | 1.01285 (12) | 0.19287 (13) | 0.0338 (4) | |
H35 | 0.7540 | 1.0336 | 0.2157 | 0.041* | |
C36 | 0.51024 (17) | 1.10216 (14) | 0.27322 (13) | 0.0374 (4) | |
H36A | 0.4932 | 1.1794 | 0.2274 | 0.045* | |
H36B | 0.4244 | 1.0916 | 0.2996 | 0.045* | |
C37 | 0.60313 (17) | 1.06979 (14) | 0.36048 (13) | 0.0359 (4) | |
C38 | 0.64078 (18) | 1.14762 (15) | 0.36848 (14) | 0.0399 (4) | |
H38 | 0.6168 | 1.2190 | 0.3163 | 0.048* | |
C39 | 0.71441 (19) | 1.11987 (17) | 0.45407 (15) | 0.0478 (5) | |
C40 | 0.75048 (19) | 1.01289 (19) | 0.53234 (14) | 0.0529 (5) | |
C41 | 0.7164 (2) | 0.93428 (16) | 0.52149 (15) | 0.0515 (5) | |
C42 | 0.64308 (19) | 0.96303 (14) | 0.43668 (14) | 0.0457 (5) | |
H42 | 0.6201 | 0.9101 | 0.4305 | 0.055* | |
C43 | 0.7160 (3) | 1.3025 (2) | 0.3906 (2) | 0.1008 (10) | |
H43A | 0.7582 | 1.3059 | 0.3294 | 0.151* | |
H43B | 0.7449 | 1.3459 | 0.4110 | 0.151* | |
H43C | 0.6195 | 1.3301 | 0.3787 | 0.151* | |
C44 | 0.9517 (3) | 0.9365 (4) | 0.6369 (2) | 0.1404 (17) | |
H44A | 0.9741 | 0.8690 | 0.6342 | 0.211* | |
H44B | 0.9807 | 0.9221 | 0.7020 | 0.211* | |
H44C | 0.9963 | 0.9837 | 0.5848 | 0.211* | |
C45 | 0.7174 (3) | 0.74947 (19) | 0.5971 (2) | 0.0951 (10) | |
H45A | 0.6205 | 0.7693 | 0.5954 | 0.143* | |
H45B | 0.7545 | 0.6808 | 0.6559 | 0.143* | |
H45C | 0.7497 | 0.7433 | 0.5372 | 0.143* | |
N1 | 0.74417 (14) | 0.95647 (11) | 0.13979 (11) | 0.0347 (3) | |
N2 | 0.23291 (15) | 0.45310 (11) | 0.14707 (11) | 0.0346 (3) | |
N3 | 0.22090 (18) | 0.34339 (14) | 0.08010 (13) | 0.0473 (4) | |
N4 | −0.16757 (15) | 0.51959 (15) | 0.17719 (13) | 0.0459 (4) | |
N5 | 0.71163 (17) | 0.86200 (13) | 0.06254 (12) | 0.0424 (4) | |
N6 | 0.34737 (15) | 1.02638 (14) | 0.18853 (13) | 0.0448 (4) | |
N7 | 0.52898 (13) | 0.94731 (11) | 0.12455 (11) | 0.0341 (3) | |
N8 | 0.02669 (13) | 0.42998 (11) | 0.13116 (11) | 0.0356 (3) | |
O1 | 0.63853 (11) | 0.47112 (9) | 0.09711 (10) | 0.0414 (3) | |
O2 | 0.50113 (11) | 0.37246 (9) | 0.12951 (10) | 0.0465 (3) | |
O3 | 0.94075 (11) | 0.11664 (9) | 0.11219 (10) | 0.0419 (3) | |
O4 | 1.06846 (12) | 0.22568 (10) | 0.03920 (11) | 0.0496 (4) | |
O5 | 0.00559 (12) | 0.87427 (10) | 0.12681 (12) | 0.0551 (4) | |
O6 | 0.14465 (11) | 0.96717 (9) | 0.11117 (10) | 0.0454 (3) | |
O7 | 0.57081 (13) | 0.72676 (11) | 0.04089 (12) | 0.0598 (4) | |
O9 | 0.44029 (11) | 0.61980 (9) | 0.10893 (9) | 0.0405 (3) | |
O11 | −0.41846 (14) | 0.67168 (11) | 0.46167 (11) | 0.0604 (4) | |
O12 | −0.30967 (15) | 0.47548 (12) | 0.61707 (10) | 0.0572 (4) | |
O13 | −0.10111 (15) | 0.32714 (11) | 0.59374 (10) | 0.0610 (4) | |
O16 | 0.75361 (16) | 1.19234 (15) | 0.46839 (12) | 0.0706 (5) | |
O17 | 0.80959 (15) | 0.98777 (15) | 0.62184 (11) | 0.0792 (5) | |
O18 | 0.75826 (17) | 0.83128 (13) | 0.60107 (11) | 0.0785 (5) | |
H2 | 0.7037 (17) | 0.2371 (14) | 0.1155 (13) | 0.037 (5)* | |
H3 | 0.8806 (19) | 0.3583 (15) | 0.0733 (14) | 0.050 (5)* | |
H3M | 0.166 (2) | 0.3156 (17) | 0.0599 (16) | 0.061 (6)* | |
H3N | 0.302 (3) | 0.3385 (17) | 0.0622 (17) | 0.066 (7)* | |
H4M | −0.211 (2) | 0.5663 (17) | 0.2015 (15) | 0.059 (6)* | |
H4N | −0.212 (2) | 0.4963 (16) | 0.1498 (15) | 0.053 (6)* | |
H5M | 0.653 (2) | 0.8363 (17) | 0.0426 (16) | 0.060 (6)* | |
H5N | 0.793 (2) | 0.8538 (16) | 0.0422 (15) | 0.055 (6)* | |
H6 | 0.2051 (19) | 0.7381 (15) | 0.1163 (14) | 0.049 (5)* | |
H6M | 0.312 (2) | 1.0579 (17) | 0.2223 (16) | 0.057 (6)* | |
H6N | 0.297 (2) | 1.0006 (16) | 0.1595 (16) | 0.059 (6)* | |
H7 | 0.3852 (18) | 0.8579 (14) | 0.0794 (14) | 0.045 (5)* | |
H1N | 0.838 (2) | 0.9362 (16) | 0.1299 (15) | 0.063 (6)* | |
H2N | 0.322 (2) | 0.4371 (16) | 0.1377 (15) | 0.059 (6)* | |
H9 | 0.521 (2) | 0.5624 (17) | 0.1033 (16) | 0.071 (6)* | |
H4 | 1.023 (2) | 0.0568 (18) | 0.1101 (17) | 0.078 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0219 (9) | 0.0276 (8) | 0.0337 (9) | −0.0027 (7) | 0.0002 (7) | −0.0160 (7) |
C2 | 0.0269 (9) | 0.0252 (8) | 0.0452 (11) | −0.0058 (7) | 0.0038 (8) | −0.0194 (8) |
C3 | 0.0262 (9) | 0.0292 (9) | 0.0452 (11) | −0.0050 (7) | 0.0035 (8) | −0.0226 (8) |
C4 | 0.0229 (9) | 0.0330 (9) | 0.0407 (10) | −0.0047 (7) | 0.0026 (8) | −0.0234 (8) |
C5 | 0.0221 (9) | 0.0285 (8) | 0.0427 (10) | −0.0023 (7) | 0.0028 (7) | −0.0185 (8) |
C6 | 0.0279 (9) | 0.0283 (9) | 0.0571 (12) | −0.0076 (7) | 0.0072 (8) | −0.0237 (9) |
C7 | 0.0266 (9) | 0.0265 (8) | 0.0444 (11) | −0.0058 (7) | 0.0047 (8) | −0.0191 (8) |
C8 | 0.0240 (9) | 0.0323 (9) | 0.0446 (10) | −0.0056 (7) | 0.0045 (8) | −0.0231 (8) |
C9 | 0.0265 (9) | 0.0347 (9) | 0.0327 (9) | −0.0075 (7) | 0.0044 (7) | −0.0150 (8) |
C11 | 0.0241 (9) | 0.0374 (9) | 0.0301 (9) | −0.0081 (7) | 0.0041 (7) | −0.0164 (8) |
C12 | 0.0295 (9) | 0.0312 (8) | 0.0310 (9) | −0.0084 (7) | 0.0014 (7) | −0.0136 (7) |
C13 | 0.0308 (9) | 0.0327 (9) | 0.0364 (10) | −0.0127 (7) | 0.0002 (8) | −0.0132 (8) |
C14 | 0.0428 (11) | 0.0383 (9) | 0.0440 (11) | −0.0165 (8) | 0.0100 (9) | −0.0237 (9) |
C15 | 0.0426 (10) | 0.0421 (10) | 0.0390 (10) | −0.0188 (8) | 0.0066 (8) | −0.0262 (9) |
C16 | 0.0499 (12) | 0.0386 (10) | 0.0423 (11) | −0.0159 (9) | 0.0111 (9) | −0.0211 (9) |
C17 | 0.0470 (11) | 0.0459 (11) | 0.0505 (12) | −0.0207 (9) | 0.0154 (9) | −0.0316 (10) |
C18 | 0.0502 (12) | 0.0553 (11) | 0.0358 (11) | −0.0284 (10) | 0.0087 (9) | −0.0255 (9) |
C19 | 0.0510 (12) | 0.0434 (10) | 0.0375 (11) | −0.0195 (9) | −0.0035 (9) | −0.0186 (9) |
C20 | 0.0440 (11) | 0.0425 (10) | 0.0430 (11) | −0.0141 (8) | 0.0019 (9) | −0.0251 (9) |
C21 | 0.0707 (16) | 0.0455 (12) | 0.0753 (16) | −0.0101 (11) | 0.0225 (13) | −0.0278 (12) |
C22 | 0.092 (2) | 0.126 (2) | 0.0558 (16) | −0.0756 (19) | 0.0142 (14) | −0.0225 (16) |
C23 | 0.0841 (18) | 0.0502 (13) | 0.0650 (16) | −0.0059 (12) | −0.0069 (13) | −0.0160 (12) |
C31 | 0.0240 (9) | 0.0303 (8) | 0.0342 (10) | −0.0056 (7) | 0.0047 (7) | −0.0139 (8) |
C33 | 0.0233 (8) | 0.0335 (8) | 0.0326 (9) | −0.0066 (7) | 0.0027 (7) | −0.0160 (8) |
C34 | 0.0252 (9) | 0.0282 (8) | 0.0330 (9) | −0.0061 (7) | 0.0012 (7) | −0.0136 (7) |
C35 | 0.0275 (9) | 0.0329 (9) | 0.0419 (10) | −0.0101 (7) | 0.0006 (8) | −0.0174 (8) |
C36 | 0.0316 (9) | 0.0381 (9) | 0.0458 (11) | −0.0058 (8) | −0.0011 (8) | −0.0249 (9) |
C37 | 0.0308 (9) | 0.0420 (10) | 0.0362 (10) | −0.0082 (8) | 0.0045 (8) | −0.0218 (8) |
C38 | 0.0382 (10) | 0.0468 (10) | 0.0383 (11) | −0.0140 (8) | 0.0051 (8) | −0.0228 (9) |
C39 | 0.0360 (11) | 0.0769 (14) | 0.0465 (12) | −0.0219 (10) | 0.0090 (9) | −0.0397 (12) |
C40 | 0.0325 (11) | 0.0889 (16) | 0.0326 (11) | −0.0085 (10) | 0.0018 (9) | −0.0315 (12) |
C41 | 0.0394 (11) | 0.0547 (12) | 0.0361 (12) | 0.0015 (9) | 0.0054 (9) | −0.0136 (10) |
C42 | 0.0445 (11) | 0.0411 (10) | 0.0450 (12) | −0.0062 (8) | 0.0021 (9) | −0.0197 (9) |
C43 | 0.133 (3) | 0.095 (2) | 0.115 (3) | −0.065 (2) | −0.005 (2) | −0.059 (2) |
C44 | 0.0425 (16) | 0.276 (5) | 0.071 (2) | −0.012 (2) | −0.0121 (14) | −0.078 (3) |
C45 | 0.100 (2) | 0.0458 (14) | 0.0776 (19) | 0.0059 (14) | 0.0209 (16) | −0.0027 (13) |
N1 | 0.0198 (7) | 0.0394 (8) | 0.0453 (9) | −0.0084 (6) | 0.0066 (7) | −0.0216 (7) |
N2 | 0.0212 (8) | 0.0363 (8) | 0.0441 (9) | −0.0082 (6) | 0.0037 (7) | −0.0179 (7) |
N3 | 0.0314 (9) | 0.0586 (10) | 0.0648 (12) | −0.0128 (8) | 0.0172 (9) | −0.0426 (10) |
N4 | 0.0233 (8) | 0.0692 (11) | 0.0641 (11) | −0.0107 (8) | 0.0064 (8) | −0.0490 (10) |
N5 | 0.0267 (9) | 0.0518 (9) | 0.0551 (10) | −0.0073 (7) | 0.0120 (8) | −0.0352 (9) |
N6 | 0.0221 (8) | 0.0691 (11) | 0.0639 (11) | −0.0116 (7) | 0.0101 (8) | −0.0503 (10) |
N7 | 0.0224 (7) | 0.0437 (8) | 0.0440 (9) | −0.0092 (6) | 0.0068 (6) | −0.0282 (7) |
N8 | 0.0250 (8) | 0.0471 (8) | 0.0424 (9) | −0.0108 (6) | 0.0062 (6) | −0.0281 (7) |
O1 | 0.0246 (6) | 0.0341 (6) | 0.0737 (9) | −0.0040 (5) | 0.0035 (6) | −0.0351 (6) |
O2 | 0.0221 (6) | 0.0393 (7) | 0.0789 (10) | −0.0073 (5) | 0.0109 (6) | −0.0314 (7) |
O3 | 0.0269 (7) | 0.0308 (6) | 0.0692 (9) | −0.0046 (5) | 0.0102 (6) | −0.0288 (6) |
O4 | 0.0303 (7) | 0.0490 (7) | 0.0849 (10) | −0.0152 (6) | 0.0240 (7) | −0.0457 (7) |
O5 | 0.0224 (7) | 0.0459 (7) | 0.1039 (12) | −0.0090 (6) | 0.0158 (7) | −0.0439 (8) |
O6 | 0.0264 (7) | 0.0348 (6) | 0.0831 (10) | −0.0036 (5) | 0.0047 (6) | −0.0380 (7) |
O7 | 0.0356 (8) | 0.0551 (8) | 0.1103 (12) | −0.0194 (6) | 0.0326 (8) | −0.0581 (9) |
O9 | 0.0280 (7) | 0.0311 (6) | 0.0629 (9) | −0.0035 (5) | 0.0092 (6) | −0.0275 (6) |
O11 | 0.0619 (9) | 0.0524 (8) | 0.0597 (9) | −0.0146 (7) | 0.0259 (8) | −0.0276 (7) |
O12 | 0.0638 (9) | 0.0793 (10) | 0.0397 (8) | −0.0374 (8) | 0.0137 (7) | −0.0293 (7) |
O13 | 0.0706 (10) | 0.0530 (8) | 0.0427 (8) | −0.0150 (7) | −0.0017 (7) | −0.0113 (7) |
O16 | 0.0699 (11) | 0.1080 (13) | 0.0700 (11) | −0.0428 (10) | 0.0050 (8) | −0.0602 (11) |
O17 | 0.0464 (9) | 0.1414 (15) | 0.0431 (9) | −0.0118 (9) | −0.0031 (7) | −0.0480 (10) |
O18 | 0.0759 (12) | 0.0664 (10) | 0.0440 (9) | 0.0056 (9) | −0.0003 (8) | −0.0050 (8) |
C1—O2 | 1.2356 (19) | C23—H23A | 0.9600 |
C1—O1 | 1.2634 (18) | C23—H23B | 0.9600 |
C1—C2 | 1.501 (2) | C23—H23C | 0.9600 |
C2—C3 | 1.304 (2) | C31—N7 | 1.3288 (19) |
C2—H2 | 0.921 (17) | C31—N5 | 1.331 (2) |
C3—C4 | 1.487 (2) | C31—N1 | 1.347 (2) |
C3—H3 | 0.956 (19) | C33—N6 | 1.327 (2) |
C4—O4 | 1.2190 (19) | C33—N7 | 1.3450 (19) |
C4—O3 | 1.2999 (19) | C33—C34 | 1.434 (2) |
C5—O5 | 1.2348 (19) | C34—C35 | 1.344 (2) |
C5—O6 | 1.2658 (19) | C34—C36 | 1.513 (2) |
C5—C6 | 1.496 (2) | C35—N1 | 1.358 (2) |
C6—C7 | 1.300 (2) | C35—H35 | 0.9300 |
C6—H6 | 0.954 (19) | C36—C37 | 1.511 (2) |
C7—C8 | 1.482 (2) | C36—H36A | 0.9700 |
C7—H7 | 0.949 (18) | C36—H36B | 0.9700 |
C8—O7 | 1.2176 (19) | C37—C38 | 1.381 (2) |
C8—O9 | 1.3016 (19) | C37—C42 | 1.382 (2) |
C9—N3 | 1.329 (2) | C38—C39 | 1.391 (3) |
C9—N8 | 1.329 (2) | C38—H38 | 0.9300 |
C9—N2 | 1.350 (2) | C39—O16 | 1.366 (2) |
C11—N4 | 1.329 (2) | C39—C40 | 1.394 (3) |
C11—N8 | 1.3377 (19) | C40—O17 | 1.376 (2) |
C11—C12 | 1.432 (2) | C40—C41 | 1.394 (3) |
C12—C13 | 1.346 (2) | C41—O18 | 1.367 (2) |
C12—C14 | 1.502 (2) | C41—C42 | 1.374 (3) |
C13—N2 | 1.361 (2) | C42—H42 | 0.9300 |
C13—H13 | 0.9300 | C43—O16 | 1.422 (3) |
C14—C15 | 1.519 (2) | C43—H43A | 0.9600 |
C14—H14A | 0.9700 | C43—H43B | 0.9600 |
C14—H14B | 0.9700 | C43—H43C | 0.9600 |
C15—C16 | 1.385 (2) | C44—O17 | 1.420 (3) |
C15—C20 | 1.387 (2) | C44—H44A | 0.9600 |
C16—C17 | 1.391 (2) | C44—H44B | 0.9600 |
C16—H16 | 0.9300 | C44—H44C | 0.9600 |
C17—O11 | 1.371 (2) | C45—O18 | 1.426 (3) |
C17—C18 | 1.383 (3) | C45—H45A | 0.9600 |
C18—O12 | 1.381 (2) | C45—H45B | 0.9600 |
C18—C19 | 1.391 (3) | C45—H45C | 0.9600 |
C19—O13 | 1.367 (2) | N1—H1N | 0.95 (2) |
C19—C20 | 1.391 (2) | N2—H2N | 0.90 (2) |
C20—H20 | 0.9300 | N3—H3M | 0.94 (2) |
C21—O11 | 1.422 (2) | N3—H3N | 0.85 (2) |
C21—H21A | 0.9600 | N4—H4M | 0.90 (2) |
C21—H21B | 0.9600 | N4—H4N | 0.88 (2) |
C21—H21C | 0.9600 | N5—H5M | 0.95 (2) |
C22—O12 | 1.403 (3) | N5—H5N | 0.86 (2) |
C22—H22A | 0.9600 | N6—H6M | 0.82 (2) |
C22—H22B | 0.9600 | N6—H6N | 0.97 (2) |
C22—H22C | 0.9600 | O3—H4 | 1.02 (2) |
C23—O13 | 1.405 (2) | O9—H9 | 1.01 (2) |
O2—C1—O1 | 125.25 (13) | N5—C31—N1 | 118.82 (15) |
O2—C1—C2 | 117.01 (14) | N6—C33—N7 | 115.39 (15) |
O1—C1—C2 | 117.73 (14) | N6—C33—C34 | 122.44 (14) |
C3—C2—C1 | 125.38 (15) | N7—C33—C34 | 122.15 (14) |
C3—C2—H2 | 120.2 (10) | C35—C34—C33 | 115.22 (14) |
C1—C2—H2 | 114.4 (10) | C35—C34—C36 | 121.89 (15) |
C2—C3—C4 | 125.01 (15) | C33—C34—C36 | 122.89 (14) |
C2—C3—H3 | 123.2 (11) | C34—C35—N1 | 122.45 (16) |
C4—C3—H3 | 111.8 (11) | C34—C35—H35 | 118.8 |
O4—C4—O3 | 123.77 (13) | N1—C35—H35 | 118.8 |
O4—C4—C3 | 120.49 (14) | C37—C36—C34 | 114.73 (13) |
O3—C4—C3 | 115.74 (14) | C37—C36—H36A | 108.6 |
O5—C5—O6 | 125.42 (13) | C34—C36—H36A | 108.6 |
O5—C5—C6 | 116.20 (14) | C37—C36—H36B | 108.6 |
O6—C5—C6 | 118.38 (14) | C34—C36—H36B | 108.6 |
C7—C6—C5 | 125.57 (16) | H36A—C36—H36B | 107.6 |
C7—C6—H6 | 121.3 (11) | C38—C37—C42 | 119.51 (17) |
C5—C6—H6 | 113.1 (11) | C38—C37—C36 | 120.43 (15) |
C6—C7—C8 | 124.19 (16) | C42—C37—C36 | 119.90 (16) |
C6—C7—H7 | 122.8 (11) | C37—C38—C39 | 120.40 (17) |
C8—C7—H7 | 113.0 (11) | C37—C38—H38 | 119.8 |
O7—C8—O9 | 123.46 (14) | C39—C38—H38 | 119.8 |
O7—C8—C7 | 120.60 (15) | O16—C39—C38 | 123.94 (19) |
O9—C8—C7 | 115.94 (14) | O16—C39—C40 | 116.18 (19) |
N3—C9—N8 | 118.84 (16) | C38—C39—C40 | 119.88 (18) |
N3—C9—N2 | 118.89 (16) | O17—C40—C41 | 120.7 (2) |
N8—C9—N2 | 122.26 (14) | O17—C40—C39 | 120.0 (2) |
N4—C11—N8 | 116.70 (16) | C41—C40—C39 | 119.08 (18) |
N4—C11—C12 | 120.75 (15) | O18—C41—C42 | 124.7 (2) |
N8—C11—C12 | 122.56 (14) | O18—C41—C40 | 115.0 (2) |
C13—C12—C11 | 115.36 (14) | C42—C41—C40 | 120.33 (18) |
C13—C12—C14 | 122.68 (15) | C41—C42—C37 | 120.72 (18) |
C11—C12—C14 | 121.78 (14) | C41—C42—H42 | 119.6 |
C12—C13—N2 | 121.90 (16) | C37—C42—H42 | 119.6 |
C12—C13—H13 | 119.0 | O16—C43—H43A | 109.5 |
N2—C13—H13 | 119.0 | O16—C43—H43B | 109.5 |
C12—C14—C15 | 117.43 (13) | H43A—C43—H43B | 109.5 |
C12—C14—H14A | 107.9 | O16—C43—H43C | 109.5 |
C15—C14—H14A | 107.9 | H43A—C43—H43C | 109.5 |
C12—C14—H14B | 107.9 | H43B—C43—H43C | 109.5 |
C15—C14—H14B | 107.9 | O17—C44—H44A | 109.5 |
H14A—C14—H14B | 107.2 | O17—C44—H44B | 109.5 |
C16—C15—C20 | 119.45 (16) | H44A—C44—H44B | 109.5 |
C16—C15—C14 | 118.23 (15) | O17—C44—H44C | 109.5 |
C20—C15—C14 | 122.20 (15) | H44A—C44—H44C | 109.5 |
C15—C16—C17 | 120.52 (17) | H44B—C44—H44C | 109.5 |
C15—C16—H16 | 119.7 | O18—C45—H45A | 109.5 |
C17—C16—H16 | 119.7 | O18—C45—H45B | 109.5 |
O11—C17—C18 | 115.39 (15) | H45A—C45—H45B | 109.5 |
O11—C17—C16 | 124.65 (17) | O18—C45—H45C | 109.5 |
C18—C17—C16 | 119.96 (16) | H45A—C45—H45C | 109.5 |
O12—C18—C17 | 119.81 (16) | H45B—C45—H45C | 109.5 |
O12—C18—C19 | 120.58 (17) | C31—N1—C35 | 119.43 (14) |
C17—C18—C19 | 119.54 (16) | C31—N1—H1N | 120.9 (12) |
O13—C19—C18 | 114.35 (16) | C35—N1—H1N | 119.5 (13) |
O13—C19—C20 | 125.47 (17) | C9—N2—C13 | 119.51 (14) |
C18—C19—C20 | 120.18 (17) | C9—N2—H2N | 119.2 (13) |
C15—C20—C19 | 120.06 (16) | C13—N2—H2N | 121.2 (13) |
C15—C20—H20 | 120.0 | C9—N3—H3M | 117.1 (12) |
C19—C20—H20 | 120.0 | C9—N3—H3N | 119.9 (15) |
O11—C21—H21A | 109.5 | H3M—N3—H3N | 121.5 (19) |
O11—C21—H21B | 109.5 | C11—N4—H4M | 118.4 (13) |
H21A—C21—H21B | 109.5 | C11—N4—H4N | 119.5 (13) |
O11—C21—H21C | 109.5 | H4M—N4—H4N | 121.6 (19) |
H21A—C21—H21C | 109.5 | C31—N5—H5M | 119.0 (12) |
H21B—C21—H21C | 109.5 | C31—N5—H5N | 121.2 (13) |
O12—C22—H22A | 109.5 | H5M—N5—H5N | 119.0 (18) |
O12—C22—H22B | 109.5 | C33—N6—H6M | 120.1 (15) |
H22A—C22—H22B | 109.5 | C33—N6—H6N | 117.4 (12) |
O12—C22—H22C | 109.5 | H6M—N6—H6N | 122.5 (19) |
H22A—C22—H22C | 109.5 | C31—N7—C33 | 118.45 (14) |
H22B—C22—H22C | 109.5 | C9—N8—C11 | 118.21 (14) |
O13—C23—H23A | 109.5 | C4—O3—H4 | 112.6 (12) |
O13—C23—H23B | 109.5 | C8—O9—H9 | 111.9 (12) |
H23A—C23—H23B | 109.5 | C17—O11—C21 | 117.11 (14) |
O13—C23—H23C | 109.5 | C18—O12—C22 | 115.41 (16) |
H23A—C23—H23C | 109.5 | C19—O13—C23 | 119.67 (15) |
H23B—C23—H23C | 109.5 | C39—O16—C43 | 117.38 (18) |
N7—C31—N5 | 118.91 (16) | C40—O17—C44 | 117.14 (17) |
N7—C31—N1 | 122.24 (14) | C41—O18—C45 | 117.2 (2) |
O2—C1—C2—C3 | 179.96 (17) | C34—C36—C37—C38 | 126.38 (16) |
O1—C1—C2—C3 | −1.2 (3) | C34—C36—C37—C42 | −58.2 (2) |
C1—C2—C3—C4 | −179.66 (16) | C42—C37—C38—C39 | −2.2 (2) |
C2—C3—C4—O4 | 166.26 (18) | C36—C37—C38—C39 | 173.20 (15) |
C2—C3—C4—O3 | −14.3 (3) | C37—C38—C39—O16 | −178.95 (16) |
O5—C5—C6—C7 | 173.97 (19) | C37—C38—C39—C40 | 0.0 (2) |
O6—C5—C6—C7 | −5.3 (3) | O16—C39—C40—O17 | 6.5 (2) |
C5—C6—C7—C8 | −177.56 (16) | C38—C39—C40—O17 | −172.56 (15) |
C6—C7—C8—O7 | 166.05 (19) | O16—C39—C40—C41 | −178.47 (16) |
C6—C7—C8—O9 | −14.0 (3) | C38—C39—C40—C41 | 2.5 (3) |
N4—C11—C12—C13 | −175.43 (16) | O17—C40—C41—O18 | −6.2 (2) |
N8—C11—C12—C13 | 4.5 (2) | C39—C40—C41—O18 | 178.72 (16) |
N4—C11—C12—C14 | −0.2 (3) | O17—C40—C41—C42 | 172.20 (16) |
N8—C11—C12—C14 | 179.74 (15) | C39—C40—C41—C42 | −2.8 (3) |
C11—C12—C13—N2 | −1.2 (2) | O18—C41—C42—C37 | 178.93 (16) |
C14—C12—C13—N2 | −176.41 (15) | C40—C41—C42—C37 | 0.7 (3) |
C13—C12—C14—C15 | −125.77 (18) | C38—C37—C42—C41 | 1.9 (3) |
C11—C12—C14—C15 | 59.3 (2) | C36—C37—C42—C41 | −173.54 (15) |
C12—C14—C15—C16 | −143.39 (17) | N7—C31—N1—C35 | 2.3 (2) |
C12—C14—C15—C20 | 40.7 (2) | N5—C31—N1—C35 | −175.45 (15) |
C20—C15—C16—C17 | 3.8 (3) | C34—C35—N1—C31 | −1.6 (2) |
C14—C15—C16—C17 | −172.26 (16) | N3—C9—N2—C13 | −175.86 (15) |
C15—C16—C17—O11 | 179.86 (17) | N8—C9—N2—C13 | 3.2 (2) |
C15—C16—C17—C18 | 0.3 (3) | C12—C13—N2—C9 | −2.4 (2) |
O11—C17—C18—O12 | −7.5 (3) | N5—C31—N7—C33 | 176.95 (15) |
C16—C17—C18—O12 | 172.09 (16) | N1—C31—N7—C33 | −0.8 (2) |
O11—C17—C18—C19 | 175.59 (16) | N6—C33—N7—C31 | 179.88 (15) |
C16—C17—C18—C19 | −4.8 (3) | C34—C33—N7—C31 | −1.4 (2) |
O12—C18—C19—O13 | 7.7 (2) | N3—C9—N8—C11 | 179.04 (16) |
C17—C18—C19—O13 | −175.49 (16) | N2—C9—N8—C11 | 0.0 (2) |
O12—C18—C19—C20 | −171.56 (16) | N4—C11—N8—C9 | 176.00 (16) |
C17—C18—C19—C20 | 5.3 (3) | C12—C11—N8—C9 | −3.9 (2) |
C16—C15—C20—C19 | −3.3 (3) | C18—C17—O11—C21 | −171.92 (18) |
C14—C15—C20—C19 | 172.61 (16) | C16—C17—O11—C21 | 8.5 (3) |
O13—C19—C20—C15 | 179.61 (17) | C17—C18—O12—C22 | 95.7 (2) |
C18—C19—C20—C15 | −1.3 (3) | C19—C18—O12—C22 | −87.4 (2) |
N6—C33—C34—C35 | −179.42 (16) | C18—C19—O13—C23 | 173.33 (18) |
N7—C33—C34—C35 | 1.9 (2) | C20—C19—O13—C23 | −7.5 (3) |
N6—C33—C34—C36 | 0.4 (3) | C38—C39—O16—C43 | 0.1 (3) |
N7—C33—C34—C36 | −178.21 (15) | C40—C39—O16—C43 | −178.9 (2) |
C33—C34—C35—N1 | −0.4 (2) | C41—C40—O17—C44 | 82.9 (3) |
C36—C34—C35—N1 | 179.74 (15) | C39—C40—O17—C44 | −102.1 (3) |
C35—C34—C36—C37 | −38.9 (2) | C42—C41—O18—C45 | −2.9 (3) |
C33—C34—C36—C37 | 141.21 (16) | C40—C41—O18—C45 | 175.50 (18) |
Experimental details
Crystal data | |
Chemical formula | C14H19N4O3·C4H3O4 |
Mr | 406.40 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.4700 (5), 14.6637 (10), 15.0285 (10) |
α, β, γ (°) | 61.535 (7), 83.550 (5), 71.020 (5) |
V (Å3) | 1915.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.4 × 0.3 × 0.15 |
Data collection | |
Diffractometer | Xcalibur, Ruby, Gemini ultra diffractometer |
Absorption correction | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.978, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16621, 6752, 5223 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.120, 1.04 |
No. of reflections | 6752 |
No. of parameters | 593 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.22 |
Computer programs: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01), SHELXL97 (Sheldrick, 1997).
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