Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101013684/de0013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013684/de0013Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013684/de0013Asup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013684/de0013Bsup4.hkl |
CCDC references: 179368; 179369; 179370
For all compounds, data collection: CAD4; cell refinement: CAD4. Data reduction: MolEN for (I); CAD4 for A, B. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP III. Software used to prepare material for publication: MSWORD for (I); MS WORD for A; MS Word for B.
<C9N4H21O5> | F(000) = 556 |
Mr = 516.57 | Dx = 1.326 Mg m−3 |
Monoclinic, C2 | Cu Kα radiation, λ = 1.54180 Å |
a = 19.008 (3) Å | Cell parameters from 25 reflections |
b = 5.073 (2) Å | θ = 18–30° |
c = 13.6723 (19) Å | µ = 0.92 mm−1 |
β = 101.109 (13)° | T = 293 K |
V = 1293.5 (6) Å3 | Needle, colourless |
Z = 2 | 0.4 × 0.05 × 0.05 mm |
CAD4 diffractometer | 1161 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 74.8°, θmin = 3.3° |
ω–2/q scans | h = −5→23 |
Absorption correction: empirical (North et al., 1968) North et al., 1968 | k = −6→6 |
Tmin = 0.955, Tmax = 1.000 | l = −17→16 |
1545 measured reflections | 2 standard reflections every 60 min |
1494 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0833P)2 + 0.7082P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.158 | (Δ/σ)max = 0.005 |
S = 1.11 | Δρmax = 0.23 e Å−3 |
1494 reflections | Δρmin = −0.23 e Å−3 |
170 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0053 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map |
<C9N4H21O5> | V = 1293.5 (6) Å3 |
Mr = 516.57 | Z = 2 |
Monoclinic, C2 | Cu Kα radiation |
a = 19.008 (3) Å | µ = 0.92 mm−1 |
b = 5.073 (2) Å | T = 293 K |
c = 13.6723 (19) Å | 0.4 × 0.05 × 0.05 mm |
β = 101.109 (13)° |
CAD4 diffractometer | 1494 independent reflections |
Absorption correction: empirical (North et al., 1968) North et al., 1968 | 1161 reflections with I > 2σ(I) |
Tmin = 0.955, Tmax = 1.000 | Rint = 0.033 |
1545 measured reflections | 2 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.053 | 2 restraints |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.23 e Å−3 |
1494 reflections | Δρmin = −0.23 e Å−3 |
170 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
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 | ||
N1 | 1.00235 (17) | 0.9908 (8) | 0.1336 (2) | 0.0397 (8) | |
H1C | 1.0318 | 0.9526 | 0.0923 | 0.060* | |
H1B | 1.0277 | 1.0472 | 0.1914 | 0.060* | |
H1A | 0.9720 | 1.1164 | 0.1068 | 0.060* | |
O1 | 0.90552 (14) | 0.7840 (7) | −0.02090 (18) | 0.0455 (8) | |
O2 | 0.91373 (17) | 0.3883 (7) | 0.0498 (2) | 0.0532 (9) | |
C1 | 0.9249 (2) | 0.6314 (9) | 0.0507 (3) | 0.0383 (9) | |
C2 | 0.96136 (19) | 0.7502 (10) | 0.1507 (3) | 0.0389 (9) | |
H2 | 0.9941 | 0.6203 | 0.1881 | 0.047* | |
C3 | 0.9056 (2) | 0.8325 (10) | 0.2122 (3) | 0.0474 (11) | |
H3A | 0.9299 | 0.9267 | 0.2708 | 0.057* | |
H3B | 0.8722 | 0.9542 | 0.1729 | 0.057* | |
C4 | 0.8631 (2) | 0.6061 (11) | 0.2458 (3) | 0.0498 (11) | |
H4A | 0.8365 | 0.5155 | 0.1878 | 0.060* | |
H4B | 0.8959 | 0.4808 | 0.2841 | 0.060* | |
C5 | 0.8117 (2) | 0.7062 (11) | 0.3087 (3) | 0.0525 (12) | |
H5A | 0.7888 | 0.5580 | 0.3348 | 0.063* | |
H5B | 0.8379 | 0.8054 | 0.3647 | 0.063* | |
N6 | 0.75720 (19) | 0.8740 (9) | 0.2502 (2) | 0.0523 (10) | |
H6 | 0.7502 | 0.8595 | 0.1864 | 0.063* | |
C7 | 0.7174 (2) | 1.0480 (11) | 0.2878 (3) | 0.0454 (11) | |
N8 | 0.72929 (19) | 1.0978 (10) | 0.3847 (2) | 0.0543 (11) | |
H8A | 0.7036 | 1.2129 | 0.4080 | 0.065* | |
H8B | 0.7626 | 1.0150 | 0.4244 | 0.065* | |
N9 | 0.6655 (2) | 1.1797 (11) | 0.2292 (3) | 0.0625 (13) | |
H9A | 0.6407 | 1.2939 | 0.2543 | 0.075* | |
H9B | 0.6568 | 1.1511 | 0.1660 | 0.075* | |
O11 | 0.64854 (18) | 0.4798 (10) | 0.4612 (2) | 0.0666 (11) | |
O12 | 0.58634 (18) | 0.5705 (11) | 0.3129 (2) | 0.0762 (14) | |
C13 | 0.5994 (2) | 0.5996 (11) | 0.4052 (3) | 0.0494 (11) | |
C14 | 0.5511 (2) | 0.7815 (13) | 0.4511 (3) | 0.0587 (13) | |
H14A | 0.5239 | 0.8933 | 0.3998 | 0.070* | |
H14B | 0.5801 | 0.8940 | 0.5004 | 0.070* | |
C15 | 0.5000 | 0.6198 (19) | 0.5000 | 0.0588 (18) | |
H15A | 0.526 (3) | 0.467 (14) | 0.549 (3) | 0.071* | |
OW | 0.72442 (17) | 0.7589 (9) | 0.0349 (2) | 0.0602 (9) | |
H1W | 0.673 (3) | 0.781 (14) | 0.006 (4) | 0.090* | |
H2W | 0.734 (3) | 0.571 (15) | 0.024 (4) | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0399 (15) | 0.034 (2) | 0.0432 (15) | −0.0008 (15) | 0.0027 (11) | −0.0036 (16) |
O1 | 0.0544 (15) | 0.0421 (19) | 0.0378 (12) | −0.0117 (15) | 0.0030 (11) | 0.0047 (14) |
O2 | 0.0531 (16) | 0.0356 (19) | 0.0653 (19) | −0.0015 (15) | −0.0027 (13) | −0.0017 (16) |
C1 | 0.0392 (17) | 0.032 (2) | 0.0438 (19) | −0.0011 (18) | 0.0088 (14) | −0.0058 (19) |
C2 | 0.0410 (18) | 0.035 (2) | 0.0402 (17) | 0.0020 (19) | 0.0054 (13) | 0.0002 (19) |
C3 | 0.054 (2) | 0.045 (3) | 0.0445 (19) | −0.001 (2) | 0.0146 (16) | −0.006 (2) |
C4 | 0.057 (2) | 0.041 (3) | 0.055 (2) | 0.004 (2) | 0.0186 (18) | 0.004 (2) |
C5 | 0.052 (2) | 0.054 (3) | 0.054 (2) | 0.002 (2) | 0.0152 (18) | 0.006 (2) |
N6 | 0.0516 (18) | 0.063 (3) | 0.0418 (16) | 0.005 (2) | 0.0085 (14) | 0.0000 (18) |
C7 | 0.0431 (19) | 0.052 (3) | 0.0414 (18) | −0.003 (2) | 0.0094 (14) | 0.002 (2) |
N8 | 0.0532 (18) | 0.067 (3) | 0.0421 (16) | 0.015 (2) | 0.0074 (14) | 0.0005 (18) |
N9 | 0.058 (2) | 0.082 (4) | 0.0442 (17) | 0.021 (2) | 0.0029 (15) | −0.003 (2) |
O11 | 0.0608 (17) | 0.090 (3) | 0.0464 (15) | 0.014 (2) | 0.0026 (12) | −0.011 (2) |
O12 | 0.068 (2) | 0.112 (4) | 0.0435 (15) | 0.013 (2) | −0.0010 (13) | −0.016 (2) |
C13 | 0.0429 (19) | 0.060 (3) | 0.045 (2) | −0.006 (2) | 0.0069 (15) | −0.008 (2) |
C14 | 0.061 (3) | 0.058 (3) | 0.061 (2) | −0.001 (3) | 0.021 (2) | −0.003 (3) |
C15 | 0.060 (4) | 0.061 (5) | 0.061 (4) | 0.000 | 0.025 (3) | 0.000 |
OW | 0.0531 (17) | 0.059 (2) | 0.0644 (18) | 0.004 (2) | 0.0010 (13) | −0.004 (2) |
N1—C2 | 1.491 (6) | N6—C7 | 1.329 (6) |
O1—C1 | 1.247 (5) | C7—N8 | 1.325 (5) |
O2—C1 | 1.251 (6) | C7—N9 | 1.326 (6) |
C1—C2 | 1.532 (5) | O11—C13 | 1.246 (6) |
C2—C3 | 1.533 (5) | O12—C13 | 1.247 (5) |
C3—C4 | 1.526 (7) | C13—C14 | 1.519 (7) |
C4—C5 | 1.508 (6) | C14—C15 | 1.521 (7) |
C5—N6 | 1.455 (6) | C15—C14i | 1.521 (7) |
O1—C1—O2 | 125.5 (4) | C7—N6—C5 | 124.9 (3) |
O1—C1—C2 | 118.1 (4) | N8—C7—N9 | 118.2 (4) |
O2—C1—C2 | 116.3 (4) | N8—C7—N6 | 121.0 (4) |
N1—C2—C1 | 110.0 (3) | N9—C7—N6 | 120.9 (4) |
N1—C2—C3 | 107.5 (4) | O11—C13—O12 | 122.9 (5) |
C1—C2—C3 | 110.8 (3) | O11—C13—C14 | 119.0 (4) |
C4—C3—C2 | 115.0 (4) | O12—C13—C14 | 118.1 (4) |
C5—C4—C3 | 110.9 (4) | C13—C14—C15 | 110.0 (5) |
N6—C5—C4 | 110.7 (3) | C14i—C15—C14 | 114.7 (7) |
O1—C1—C2—N1 | −31.3 (5) | C5—N6—C7—N8 | 5.9 (7) |
O2—C1—C2—N1 | 152.5 (4) | C5—N6—C7—N9 | −175.3 (5) |
O1—C1—C2—C3 | 87.4 (5) | O11—C13—C14—C15 | −73.6 (5) |
O2—C1—C2—C3 | −88.8 (5) | O12—C13—C14—C15 | 104.0 (5) |
N1—C2—C3—C4 | −174.3 (3) | C13—C14—C15—C14i | 179.8 (4) |
C1—C2—C3—C4 | 65.4 (5) | H1A—N1—C2—H2 | −172.6 |
C2—C3—C4—C5 | 177.9 (3) | H1B—N1—C2—C1 | −173.0 |
C3—C4—C5—N6 | 64.9 (5) | H1C—N1—C2—C3 | −173.7 |
C4—C5—N6—C7 | −160.2 (5) | O11—C13—C14—C15 | −73.6 (5) |
Symmetry code: (i) −x+1, y, −z+1. |
<C11H19N3O7> | Dx = 1.407 Mg m−3 |
Mr = 1221.17 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 8.335 (1) Å | θ = 10–30° |
b = 8.856 (1) Å | µ = 1.01 mm−1 |
c = 19.522 (2) Å | T = 293 K |
V = 1441.0 (3) Å3 | Needle, colourless |
Z = 4 | 0.56 × 0.38 × 0.06 mm |
F(000) = 648 |
CAD4 diffractometer | 1295 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 74.9°, θmin = 4.5° |
ω–2/q scans | h = 0→9 |
Absorption correction: cylinder (Dwiggins, 1975) Dwiggins JR Acta Cryst.(1975)A31,146-148 | k = 0→11 |
Tmin = 0.844, Tmax = 0.848 | l = 0→24 |
1609 measured reflections | 3 standard reflections every 60 min |
1609 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.3704P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.144 | (Δ/σ)max = 0.004 |
S = 1.16 | Δρmax = 0.24 e Å−3 |
1609 reflections | Δρmin = −0.29 e Å−3 |
199 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.028 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map |
<C11H19N3O7> | V = 1441.0 (3) Å3 |
Mr = 1221.17 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 8.335 (1) Å | µ = 1.01 mm−1 |
b = 8.856 (1) Å | T = 293 K |
c = 19.522 (2) Å | 0.56 × 0.38 × 0.06 mm |
CAD4 diffractometer | 1609 independent reflections |
Absorption correction: cylinder (Dwiggins, 1975) Dwiggins JR Acta Cryst.(1975)A31,146-148 | 1295 reflections with I > 2σ(I) |
Tmin = 0.844, Tmax = 0.848 | Rint = 0.000 |
1609 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.055 | 1 restraint |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.24 e Å−3 |
1609 reflections | Δρmin = −0.29 e Å−3 |
199 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
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 | ||
O1 | 0.7051 (4) | 0.9085 (4) | 0.50718 (17) | 0.0532 (9) | |
O2 | 0.9273 (5) | 0.8547 (4) | 0.44986 (19) | 0.0631 (11) | |
N1 | 0.7349 (5) | 0.6924 (4) | 0.59850 (16) | 0.0380 (9) | |
H1C | 0.7450 | 0.7800 | 0.6209 | 0.057* | |
H1B | 0.7567 | 0.6167 | 0.6267 | 0.057* | |
H1A | 0.6349 | 0.6840 | 0.5830 | 0.057* | |
C1 | 0.8250 (6) | 0.8305 (4) | 0.4951 (2) | 0.0367 (10) | |
C2 | 0.8485 (6) | 0.6900 (4) | 0.5399 (2) | 0.0366 (10) | |
H2 | 0.9581 | 0.6912 | 0.5581 | 0.044* | |
C3 | 0.8258 (6) | 0.5446 (4) | 0.4981 (2) | 0.0386 (10) | |
H3A | 0.7144 | 0.5372 | 0.4841 | 0.046* | |
H3B | 0.8907 | 0.5507 | 0.4570 | 0.046* | |
C4 | 0.8701 (6) | 0.4062 (4) | 0.53638 (19) | 0.0348 (10) | |
N5 | 1.0285 (5) | 0.3733 (4) | 0.55244 (17) | 0.0379 (9) | |
H5 | 1.1105 | 0.4266 | 0.5410 | 0.045* | |
C6 | 1.0327 (7) | 0.2458 (5) | 0.5883 (2) | 0.0429 (11) | |
H6 | 1.1245 | 0.1993 | 0.6053 | 0.051* | |
N7 | 0.8853 (5) | 0.1969 (4) | 0.59576 (17) | 0.0404 (9) | |
H7 | 0.8579 | 0.1159 | 0.6171 | 0.048* | |
C8 | 0.7822 (6) | 0.2941 (5) | 0.5645 (2) | 0.0401 (10) | |
H8 | 0.6711 | 0.2850 | 0.5628 | 0.048* | |
O11 | 0.8000 (5) | −0.0486 (3) | 0.66912 (15) | 0.0499 (9) | |
O12 | 0.6558 (5) | −0.1515 (3) | 0.75151 (17) | 0.0592 (11) | |
C13 | 0.7153 (6) | −0.0394 (5) | 0.7220 (2) | 0.0404 (11) | |
C14 | 0.6840 (6) | 0.1155 (5) | 0.7516 (2) | 0.0433 (11) | |
H14A | 0.6037 | 0.1078 | 0.7874 | 0.052* | |
H14B | 0.6420 | 0.1810 | 0.7161 | 0.052* | |
C15 | 0.8354 (7) | 0.1842 (5) | 0.7810 (2) | 0.0449 (12) | |
H15A | 0.9134 | 0.1968 | 0.7445 | 0.054* | |
H15B | 0.8807 | 0.1155 | 0.8145 | 0.054* | |
C16 | 0.8047 (8) | 0.3367 (4) | 0.8148 (2) | 0.0484 (13) | |
H16A | 0.7137 | 0.3264 | 0.8455 | 0.058* | |
H16B | 0.8973 | 0.3623 | 0.8425 | 0.058* | |
C17 | 0.7721 (6) | 0.4652 (5) | 0.7668 (2) | 0.0406 (11) | |
O18 | 0.7879 (5) | 0.4615 (3) | 0.70578 (15) | 0.0593 (11) | |
O19 | 0.7252 (6) | 0.5867 (3) | 0.80052 (16) | 0.0605 (11) | |
H19 | 0.7036 | 0.6540 | 0.7732 | 0.091* | |
OW | 0.8968 (6) | 0.1499 (4) | 0.39960 (19) | 0.0595 (10) | |
H1W | 0.899 (9) | 0.138 (7) | 0.352 (3) | 0.089* | |
H2W | 0.897 (9) | 0.064 (8) | 0.414 (3) | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.051 (2) | 0.0405 (16) | 0.068 (2) | 0.0145 (17) | 0.0090 (18) | 0.0228 (16) |
O2 | 0.071 (3) | 0.053 (2) | 0.065 (2) | 0.0167 (19) | 0.021 (2) | 0.0304 (18) |
N1 | 0.054 (2) | 0.0244 (14) | 0.0356 (16) | 0.0018 (17) | 0.0024 (17) | 0.0039 (14) |
C1 | 0.048 (3) | 0.0243 (19) | 0.038 (2) | −0.0014 (18) | −0.006 (2) | 0.0042 (16) |
C2 | 0.053 (3) | 0.0253 (18) | 0.0315 (18) | −0.001 (2) | −0.006 (2) | 0.0047 (16) |
C3 | 0.058 (3) | 0.0285 (19) | 0.0294 (18) | 0.001 (2) | −0.003 (2) | 0.0007 (16) |
C4 | 0.051 (3) | 0.0238 (17) | 0.0296 (18) | −0.002 (2) | 0.000 (2) | −0.0026 (15) |
N5 | 0.046 (2) | 0.0249 (16) | 0.0423 (19) | −0.0007 (17) | 0.0036 (17) | 0.0045 (15) |
C6 | 0.055 (3) | 0.030 (2) | 0.043 (2) | 0.005 (2) | 0.004 (2) | 0.0062 (19) |
N7 | 0.060 (3) | 0.0222 (15) | 0.0390 (18) | −0.0060 (18) | 0.0061 (18) | 0.0060 (15) |
C8 | 0.051 (3) | 0.030 (2) | 0.040 (2) | −0.003 (2) | 0.002 (2) | −0.0033 (17) |
O11 | 0.082 (3) | 0.0223 (13) | 0.0449 (16) | −0.0039 (16) | 0.0140 (18) | −0.0025 (12) |
O12 | 0.094 (3) | 0.0238 (14) | 0.0592 (19) | −0.0012 (18) | 0.026 (2) | 0.0058 (14) |
C13 | 0.059 (3) | 0.0230 (19) | 0.039 (2) | 0.000 (2) | 0.001 (2) | 0.0012 (16) |
C14 | 0.052 (3) | 0.025 (2) | 0.053 (2) | 0.0017 (19) | 0.004 (2) | −0.0024 (19) |
C15 | 0.059 (3) | 0.027 (2) | 0.048 (2) | 0.007 (2) | −0.004 (2) | −0.0005 (18) |
C16 | 0.080 (4) | 0.029 (2) | 0.036 (2) | −0.001 (2) | −0.007 (2) | −0.0020 (17) |
C17 | 0.060 (3) | 0.0245 (19) | 0.038 (2) | −0.004 (2) | −0.003 (2) | −0.0029 (17) |
O18 | 0.108 (3) | 0.0328 (15) | 0.0368 (16) | 0.004 (2) | 0.001 (2) | −0.0013 (13) |
O19 | 0.109 (3) | 0.0277 (14) | 0.0451 (17) | 0.010 (2) | −0.003 (2) | −0.0039 (13) |
OW | 0.079 (3) | 0.045 (2) | 0.055 (2) | 0.002 (2) | −0.003 (2) | 0.0101 (17) |
O1—C1 | 1.237 (5) | N7—C8 | 1.361 (6) |
O2—C1 | 1.247 (5) | O11—C13 | 1.253 (5) |
N1—C2 | 1.485 (5) | O12—C13 | 1.251 (5) |
C1—C2 | 1.533 (5) | C13—C14 | 1.511 (6) |
C2—C3 | 1.536 (5) | C14—C15 | 1.514 (7) |
C3—C4 | 1.482 (5) | C15—C16 | 1.525 (6) |
C4—C8 | 1.351 (6) | C16—C17 | 1.499 (5) |
C4—N5 | 1.388 (6) | C17—O18 | 1.200 (5) |
N5—C6 | 1.329 (5) | C17—O19 | 1.320 (5) |
C6—N7 | 1.311 (7) | ||
O1—C1—O2 | 126.2 (4) | C6—N7—C8 | 109.5 (4) |
O1—C1—C2 | 116.6 (4) | C4—C8—N7 | 107.8 (4) |
O2—C1—C2 | 117.2 (4) | O12—C13—O11 | 123.4 (4) |
N1—C2—C1 | 110.1 (4) | O12—C13—C14 | 118.4 (4) |
N1—C2—C3 | 110.2 (3) | O11—C13—C14 | 118.2 (4) |
C1—C2—C3 | 111.2 (3) | C13—C14—C15 | 111.4 (4) |
C4—C3—C2 | 113.3 (3) | C14—C15—C16 | 112.3 (4) |
C8—C4—N5 | 105.6 (4) | C17—C16—C15 | 115.6 (3) |
C8—C4—C3 | 132.7 (5) | O18—C17—O19 | 123.3 (4) |
N5—C4—C3 | 121.6 (4) | O18—C17—C16 | 125.5 (4) |
C6—N5—C4 | 108.8 (4) | O19—C17—C16 | 111.2 (3) |
N7—C6—N5 | 108.3 (4) | ||
O1—C1—C2—N1 | −10.8 (5) | N5—C4—C8—N7 | −0.5 (5) |
O2—C1—C2—N1 | 169.8 (4) | C3—C4—C8—N7 | −178.0 (4) |
O1—C1—C2—C3 | 111.6 (5) | C6—N7—C8—C4 | 0.5 (5) |
O2—C1—C2—C3 | −67.8 (5) | O12—C13—C14—C15 | 111.6 (5) |
N1—C2—C3—C4 | −66.0 (5) | O11—C13—C14—C15 | −68.2 (6) |
C1—C2—C3—C4 | 171.7 (4) | C13—C14—C15—C16 | −176.7 (3) |
C2—C3—C4—C8 | 107.2 (5) | C14—C15—C16—C17 | −72.8 (6) |
C2—C3—C4—N5 | −70.0 (5) | C15—C16—C17—O18 | −9.8 (8) |
C8—C4—N5—C6 | 0.4 (5) | C15—C16—C17—O19 | 171.3 (5) |
C3—C4—N5—C6 | 178.2 (4) | H1A—N1—C2—H2 | −175.2 |
C4—N5—C6—N7 | 0.0 (5) | H1B—N1—C2—C1 | −173.6 |
N5—C6—N7—C8 | −0.3 (5) | H1C—N1—C2—C3 | −176.7 |
C34H52N12O16 | Z = 2 |
Mr = 884.88 | F(000) = 468 |
Triclinic, P1 | Dx = 1.446 Mg m−3 |
a = 5.791 (1) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 13.110 (3) Å | Cell parameters from 25 reflections |
c = 14.360 (3) Å | θ = 10–30° |
α = 110.46 (2)° | µ = 0.99 mm−1 |
β = 89.78 (1)° | T = 293 K |
γ = 95.62 (2)° | Platy, colourless |
V = 1016.0 (4) Å3 | 0.8 × 0.6 × 0.5 mm |
CAD4 diffractometer | 4023 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 75.1°, θmin = 3.3° |
ω–2/q scans | h = 0→7 |
Absorption correction: numerical (Dwiggins, 1975) Dwiggins JR Acta.Cryst 1975,A31,146 | k = −16→16 |
Tmin = 0.604, Tmax = 0.629 | l = −17→17 |
6281 measured reflections | 3 standard reflections every 60 min |
4174 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0853P)2 + 0.1628P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.124 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.33 e Å−3 |
4174 reflections | Δρmin = −0.37 e Å−3 |
566 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0187 (17) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map |
C34H52N12O16 | γ = 95.62 (2)° |
Mr = 884.88 | V = 1016.0 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.791 (1) Å | Cu Kα radiation |
b = 13.110 (3) Å | µ = 0.99 mm−1 |
c = 14.360 (3) Å | T = 293 K |
α = 110.46 (2)° | 0.8 × 0.6 × 0.5 mm |
β = 89.78 (1)° |
CAD4 diffractometer | 4174 independent reflections |
Absorption correction: numerical (Dwiggins, 1975) Dwiggins JR Acta.Cryst 1975,A31,146 | 4023 reflections with I > 2σ(I) |
Tmin = 0.604, Tmax = 0.629 | Rint = 0.031 |
6281 measured reflections | 3 standard reflections every 60 min |
R[F2 > 2σ(F2)] = 0.042 | 3 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.33 e Å−3 |
4174 reflections | Δρmin = −0.37 e Å−3 |
566 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
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 | ||
N1 | 1.1322 (4) | 0.0507 (2) | 0.39355 (19) | 0.0328 (5) | |
H1B | 1.0082 | 0.0265 | 0.3525 | 0.049* | |
H1A | 1.1867 | 0.1171 | 0.3951 | 0.049* | |
H1C | 1.0925 | 0.0538 | 0.4544 | 0.049* | |
O1 | 1.5593 (4) | 0.14124 (19) | 0.40499 (18) | 0.0421 (5) | |
O2 | 1.6890 (4) | −0.0052 (2) | 0.2905 (2) | 0.0448 (6) | |
C1 | 1.5420 (5) | 0.0424 (2) | 0.3496 (2) | 0.0312 (6) | |
C2 | 1.3162 (5) | −0.0259 (2) | 0.3577 (2) | 0.0286 (5) | |
H2 | 1.3428 | −0.0576 | 0.4087 | 0.034* | |
C3 | 1.2419 (5) | −0.1190 (3) | 0.2621 (2) | 0.0330 (6) | |
H3A | 1.2103 | −0.0893 | 0.2109 | 0.040* | |
H3B | 1.3678 | −0.1646 | 0.2405 | 0.040* | |
C4 | 1.0298 (5) | −0.1877 (2) | 0.2744 (2) | 0.0312 (6) | |
N5 | 0.9020 (5) | −0.2579 (2) | 0.1928 (2) | 0.0354 (5) | |
H5 | 0.9352 | −0.2694 | 0.1318 | 0.042* | |
C6 | 0.7183 (6) | −0.3050 (3) | 0.2238 (3) | 0.0401 (7) | |
H6 | 0.6053 | −0.3562 | 0.1828 | 0.048* | |
N7 | 0.7218 (5) | −0.2675 (2) | 0.3221 (2) | 0.0379 (6) | |
H7 | 0.6206 | −0.2861 | 0.3587 | 0.046* | |
C8 | 0.9156 (6) | −0.1936 (3) | 0.3556 (2) | 0.0357 (6) | |
H8 | 0.9603 | −0.1548 | 0.4216 | 0.043* | |
N11 | 0.6451 (4) | 0.1831 (2) | 0.20463 (19) | 0.0310 (5) | |
H11C | 0.6180 | 0.1194 | 0.2141 | 0.047* | |
H11B | 0.7894 | 0.2120 | 0.2253 | 0.047* | |
H11A | 0.6276 | 0.1722 | 0.1402 | 0.047* | |
O11 | 0.2110 (4) | 0.09818 (19) | 0.19774 (19) | 0.0418 (5) | |
O12 | 0.0773 (4) | 0.2554 (2) | 0.2891 (2) | 0.0502 (6) | |
C11 | 0.2348 (5) | 0.1981 (3) | 0.2481 (2) | 0.0311 (6) | |
C12 | 0.4788 (5) | 0.2589 (2) | 0.2617 (2) | 0.0289 (5) | |
H12 | 0.5252 | 0.2854 | 0.3324 | 0.035* | |
C13 | 0.4758 (5) | 0.3572 (3) | 0.2276 (3) | 0.0365 (6) | |
H13A | 0.4046 | 0.3320 | 0.1614 | 0.044* | |
H13B | 0.3787 | 0.4085 | 0.2716 | 0.044* | |
C14 | 0.7085 (6) | 0.4164 (2) | 0.2257 (2) | 0.0332 (6) | |
N15 | 0.8324 (5) | 0.4821 (2) | 0.3097 (2) | 0.0358 (5) | |
H15 | 0.7910 | 0.4938 | 0.3698 | 0.043* | |
C16 | 1.0293 (6) | 0.5250 (3) | 0.2824 (3) | 0.0394 (7) | |
H16 | 1.1433 | 0.5729 | 0.3257 | 0.047* | |
N17 | 1.0363 (5) | 0.4889 (2) | 0.1846 (2) | 0.0376 (6) | |
H17 | 1.1461 | 0.5052 | 0.1502 | 0.045* | |
C18 | 0.8364 (6) | 0.4204 (3) | 0.1473 (2) | 0.0366 (6) | |
H18 | 0.7962 | 0.3836 | 0.0804 | 0.044* | |
N21 | 1.0364 (4) | 0.1714 (2) | 0.91599 (18) | 0.0304 (5) | |
H21A | 1.0259 | 0.1311 | 0.8515 | 0.046* | |
H21C | 1.0855 | 0.2404 | 0.9236 | 0.046* | |
H21B | 0.8976 | 0.1689 | 0.9424 | 0.046* | |
O21 | 1.4886 (4) | 0.1694 (2) | 0.86203 (17) | 0.0451 (6) | |
O22 | 1.6074 (4) | 0.1685 (2) | 1.00806 (17) | 0.0406 (5) | |
C21 | 1.4536 (5) | 0.1594 (2) | 0.9435 (2) | 0.0296 (5) | |
C22 | 1.2027 (5) | 0.1280 (2) | 0.9666 (2) | 0.0289 (5) | |
H22 | 1.1826 | 0.1581 | 1.0386 | 0.035* | |
C23 | 1.1633 (5) | 0.0026 (3) | 0.9310 (3) | 0.0373 (6) | |
H23A | 1.1795 | −0.0254 | 0.8595 | 0.045* | |
H23B | 1.2866 | −0.0229 | 0.9600 | 0.045* | |
C24 | 0.9364 (5) | −0.0474 (2) | 0.9538 (2) | 0.0339 (6) | |
N25 | 0.8733 (5) | −0.0390 (2) | 1.0482 (2) | 0.0360 (5) | |
H25 | 0.9488 | −0.0003 | 1.1025 | 0.043* | |
C26 | 0.6709 (6) | −0.1026 (3) | 1.0402 (3) | 0.0385 (7) | |
H26 | 0.5929 | −0.1115 | 1.0941 | 0.046* | |
N27 | 0.5981 (5) | −0.1504 (2) | 0.9473 (2) | 0.0386 (6) | |
C28 | 0.7637 (6) | −0.1157 (3) | 0.8920 (3) | 0.0380 (7) | |
H28 | 0.7582 | −0.1360 | 0.8232 | 0.046* | |
N31 | 0.5204 (4) | 0.0351 (2) | 0.66261 (19) | 0.0330 (5) | |
H31C | 0.5316 | −0.0365 | 0.6441 | 0.050* | |
H31B | 0.3843 | 0.0460 | 0.6411 | 0.050* | |
H31A | 0.5309 | 0.0649 | 0.7286 | 0.050* | |
O31 | 0.9685 (4) | 0.0336 (2) | 0.71857 (16) | 0.0418 (5) | |
O32 | 1.0943 (4) | 0.0404 (2) | 0.57494 (18) | 0.0438 (5) | |
C31 | 0.9412 (5) | 0.0497 (2) | 0.6399 (2) | 0.0298 (5) | |
C32 | 0.7118 (5) | 0.0866 (2) | 0.6191 (2) | 0.0296 (6) | |
H32 | 0.6842 | 0.0626 | 0.5470 | 0.036* | |
C33 | 0.7135 (6) | 0.2117 (3) | 0.6634 (3) | 0.0381 (7) | |
H33A | 0.5665 | 0.2315 | 0.6463 | 0.046* | |
H33B | 0.7260 | 0.2345 | 0.7353 | 0.046* | |
C34 | 0.9050 (6) | 0.2729 (3) | 0.6289 (2) | 0.0338 (6) | |
N35 | 0.9110 (5) | 0.2754 (2) | 0.5337 (2) | 0.0383 (6) | |
H35 | 0.8087 | 0.2431 | 0.4867 | 0.046* | |
C36 | 1.1052 (7) | 0.3371 (3) | 0.5276 (3) | 0.0430 (7) | |
H36 | 1.1487 | 0.3518 | 0.4707 | 0.052* | |
N37 | 1.2258 (6) | 0.3741 (3) | 0.6117 (2) | 0.0465 (7) | |
C38 | 1.1006 (6) | 0.3344 (3) | 0.6758 (2) | 0.0424 (7) | |
H38 | 1.1441 | 0.3480 | 0.7417 | 0.051* | |
O41 | 0.3625 (5) | 0.5231 (3) | 1.0737 (2) | 0.0558 (7) | |
O42 | 0.1769 (5) | 0.3925 (2) | 0.9464 (2) | 0.0571 (7) | |
C43 | 0.3421 (6) | 0.4642 (3) | 0.9825 (3) | 0.0385 (7) | |
C44 | 0.5250 (6) | 0.4836 (3) | 0.9135 (3) | 0.0446 (8) | |
H44A | 0.4491 | 0.5005 | 0.8614 | 0.053* | |
H44B | 0.5951 | 0.4161 | 0.8822 | 0.053* | |
C45 | 0.7182 (6) | 0.5750 (3) | 0.9622 (2) | 0.0367 (6) | |
H45A | 0.6492 | 0.6419 | 0.9974 | 0.044* | |
H45B | 0.8038 | 0.5558 | 1.0105 | 0.044* | |
C46 | 0.8861 (6) | 0.5959 (3) | 0.8875 (3) | 0.0417 (7) | |
H46A | 0.9503 | 0.5281 | 0.8508 | 0.050* | |
H46B | 0.8003 | 0.6169 | 0.8403 | 0.050* | |
C47 | 1.0839 (5) | 0.6835 (2) | 0.9334 (2) | 0.0350 (6) | |
O48 | 1.1069 (5) | 0.7359 (2) | 1.02118 (19) | 0.0497 (6) | |
O49 | 1.2310 (5) | 0.6991 (2) | 0.8683 (2) | 0.0506 (6) | |
H49 | 1.3372 | 0.7452 | 0.8975 | 0.076* | |
O51 | 1.4102 (5) | 0.6831 (3) | 0.4302 (2) | 0.0590 (8) | |
O52 | 1.5795 (5) | 0.8291 (2) | 0.5483 (3) | 0.0640 (9) | |
C53 | 1.4250 (6) | 0.7517 (3) | 0.5182 (3) | 0.0421 (7) | |
C54 | 1.2452 (7) | 0.7355 (3) | 0.5909 (3) | 0.0511 (9) | |
H54A | 1.3243 | 0.7213 | 0.6439 | 0.061* | |
H54B | 1.1744 | 0.8031 | 0.6206 | 0.061* | |
C55 | 1.0551 (7) | 0.6435 (3) | 0.5456 (3) | 0.0438 (8) | |
H55A | 1.1246 | 0.5766 | 0.5112 | 0.053* | |
H55B | 0.9652 | 0.6604 | 0.4970 | 0.053* | |
C56 | 0.8948 (7) | 0.6253 (4) | 0.6232 (3) | 0.0520 (9) | |
H56A | 0.9867 | 0.6096 | 0.6719 | 0.062* | |
H56B | 0.8268 | 0.6928 | 0.6574 | 0.062* | |
C57 | 0.7019 (6) | 0.5345 (3) | 0.5834 (3) | 0.0420 (7) | |
O58 | 0.6596 (5) | 0.4840 (2) | 0.49561 (19) | 0.0512 (6) | |
O59 | 0.5838 (6) | 0.5172 (3) | 0.6544 (2) | 0.0648 (9) | |
H59 | 0.4664 | 0.4759 | 0.6307 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0284 (12) | 0.0358 (12) | 0.0312 (12) | −0.0013 (9) | 0.0036 (9) | 0.0095 (10) |
O1 | 0.0392 (12) | 0.0397 (12) | 0.0423 (12) | −0.0127 (9) | −0.0042 (10) | 0.0124 (10) |
O2 | 0.0257 (11) | 0.0527 (14) | 0.0559 (14) | −0.0006 (9) | 0.0066 (10) | 0.0203 (11) |
C1 | 0.0261 (13) | 0.0377 (14) | 0.0324 (14) | −0.0059 (11) | −0.0037 (11) | 0.0178 (11) |
C2 | 0.0257 (13) | 0.0318 (13) | 0.0295 (13) | −0.0018 (10) | 0.0002 (10) | 0.0133 (11) |
C3 | 0.0289 (14) | 0.0342 (14) | 0.0325 (14) | −0.0045 (11) | 0.0053 (11) | 0.0097 (12) |
C4 | 0.0323 (15) | 0.0270 (13) | 0.0333 (14) | −0.0023 (11) | 0.0028 (11) | 0.0106 (11) |
N5 | 0.0359 (13) | 0.0333 (12) | 0.0328 (13) | −0.0041 (10) | 0.0022 (10) | 0.0084 (10) |
C6 | 0.0369 (16) | 0.0343 (16) | 0.0437 (17) | −0.0075 (12) | 0.0013 (13) | 0.0098 (13) |
N7 | 0.0343 (14) | 0.0335 (13) | 0.0437 (14) | −0.0056 (10) | 0.0068 (11) | 0.0131 (11) |
C8 | 0.0365 (16) | 0.0330 (14) | 0.0350 (14) | −0.0066 (12) | 0.0024 (12) | 0.0114 (12) |
N11 | 0.0267 (12) | 0.0332 (12) | 0.0329 (12) | −0.0017 (9) | 0.0034 (9) | 0.0125 (9) |
O11 | 0.0352 (11) | 0.0382 (12) | 0.0474 (13) | −0.0102 (9) | −0.0002 (9) | 0.0128 (10) |
O12 | 0.0251 (11) | 0.0568 (15) | 0.0568 (15) | −0.0001 (10) | 0.0075 (10) | 0.0064 (12) |
C11 | 0.0268 (13) | 0.0391 (15) | 0.0267 (12) | −0.0031 (11) | 0.0004 (10) | 0.0125 (11) |
C12 | 0.0246 (12) | 0.0332 (13) | 0.0274 (12) | −0.0006 (10) | 0.0011 (10) | 0.0095 (10) |
C13 | 0.0313 (15) | 0.0353 (15) | 0.0448 (16) | 0.0004 (12) | 0.0015 (12) | 0.0171 (13) |
C14 | 0.0343 (15) | 0.0255 (13) | 0.0405 (15) | −0.0003 (11) | 0.0029 (12) | 0.0131 (11) |
N15 | 0.0363 (14) | 0.0312 (12) | 0.0377 (13) | −0.0018 (10) | 0.0034 (11) | 0.0107 (10) |
C16 | 0.0361 (16) | 0.0316 (14) | 0.0469 (18) | −0.0043 (12) | 0.0031 (13) | 0.0113 (13) |
N17 | 0.0333 (13) | 0.0336 (13) | 0.0463 (15) | −0.0027 (10) | 0.0054 (11) | 0.0161 (11) |
C18 | 0.0382 (16) | 0.0322 (14) | 0.0381 (15) | −0.0017 (12) | 0.0034 (13) | 0.0120 (12) |
N21 | 0.0257 (11) | 0.0326 (12) | 0.0321 (12) | −0.0010 (9) | 0.0022 (9) | 0.0114 (9) |
O21 | 0.0330 (11) | 0.0695 (16) | 0.0339 (11) | −0.0038 (10) | 0.0065 (9) | 0.0222 (11) |
O22 | 0.0245 (10) | 0.0636 (15) | 0.0333 (10) | −0.0008 (9) | 0.0006 (8) | 0.0178 (10) |
C21 | 0.0232 (12) | 0.0335 (13) | 0.0274 (13) | −0.0021 (10) | 0.0031 (10) | 0.0064 (10) |
C22 | 0.0237 (13) | 0.0345 (14) | 0.0263 (12) | −0.0029 (10) | 0.0026 (10) | 0.0095 (10) |
C23 | 0.0271 (14) | 0.0333 (15) | 0.0519 (18) | 0.0018 (11) | 0.0085 (12) | 0.0157 (13) |
C24 | 0.0290 (14) | 0.0293 (13) | 0.0422 (16) | −0.0002 (11) | 0.0033 (12) | 0.0121 (12) |
N25 | 0.0325 (13) | 0.0346 (13) | 0.0388 (13) | −0.0017 (10) | 0.0000 (10) | 0.0118 (10) |
C26 | 0.0355 (16) | 0.0369 (15) | 0.0451 (17) | −0.0003 (12) | 0.0083 (13) | 0.0180 (13) |
N27 | 0.0308 (13) | 0.0333 (13) | 0.0496 (15) | −0.0043 (10) | 0.0028 (11) | 0.0139 (11) |
C28 | 0.0364 (16) | 0.0362 (15) | 0.0390 (15) | −0.0009 (13) | 0.0033 (12) | 0.0115 (12) |
N31 | 0.0260 (12) | 0.0383 (13) | 0.0333 (12) | −0.0040 (9) | 0.0030 (9) | 0.0126 (10) |
O31 | 0.0400 (12) | 0.0582 (14) | 0.0290 (10) | 0.0074 (10) | 0.0003 (9) | 0.0169 (10) |
O32 | 0.0266 (11) | 0.0695 (16) | 0.0380 (11) | 0.0075 (10) | 0.0095 (9) | 0.0219 (11) |
C31 | 0.0251 (12) | 0.0354 (14) | 0.0262 (12) | −0.0003 (10) | −0.0003 (10) | 0.0082 (10) |
C32 | 0.0238 (13) | 0.0356 (14) | 0.0273 (12) | −0.0030 (10) | 0.0030 (10) | 0.0101 (11) |
C33 | 0.0328 (15) | 0.0361 (15) | 0.0460 (17) | 0.0037 (12) | 0.0105 (13) | 0.0150 (13) |
C34 | 0.0346 (15) | 0.0322 (14) | 0.0343 (14) | 0.0004 (11) | 0.0010 (11) | 0.0120 (11) |
N35 | 0.0408 (14) | 0.0345 (13) | 0.0365 (13) | −0.0065 (11) | −0.0028 (11) | 0.0112 (11) |
C36 | 0.0480 (19) | 0.0375 (16) | 0.0409 (17) | −0.0061 (13) | 0.0078 (14) | 0.0134 (13) |
N37 | 0.0438 (16) | 0.0446 (15) | 0.0453 (15) | −0.0130 (12) | 0.0038 (13) | 0.0131 (12) |
C38 | 0.0392 (17) | 0.0469 (18) | 0.0351 (15) | −0.0068 (14) | −0.0004 (13) | 0.0098 (13) |
O41 | 0.0436 (14) | 0.0689 (18) | 0.0446 (14) | −0.0248 (13) | 0.0047 (11) | 0.0151 (13) |
O42 | 0.0447 (15) | 0.0421 (13) | 0.0728 (19) | −0.0178 (11) | 0.0027 (13) | 0.0117 (13) |
C43 | 0.0334 (15) | 0.0315 (14) | 0.0498 (18) | −0.0041 (12) | −0.0009 (13) | 0.0151 (13) |
C44 | 0.0416 (18) | 0.0384 (16) | 0.0444 (17) | −0.0105 (14) | 0.0048 (14) | 0.0068 (13) |
C45 | 0.0372 (16) | 0.0325 (14) | 0.0371 (15) | −0.0057 (12) | 0.0029 (12) | 0.0104 (12) |
C46 | 0.0395 (17) | 0.0415 (17) | 0.0378 (15) | −0.0077 (13) | 0.0068 (13) | 0.0093 (13) |
C47 | 0.0322 (15) | 0.0341 (15) | 0.0376 (15) | 0.0005 (12) | 0.0066 (12) | 0.0121 (12) |
O48 | 0.0493 (15) | 0.0530 (14) | 0.0366 (12) | −0.0165 (11) | 0.0052 (11) | 0.0088 (11) |
O49 | 0.0439 (14) | 0.0543 (15) | 0.0426 (13) | −0.0162 (11) | 0.0108 (11) | 0.0090 (11) |
O51 | 0.0546 (16) | 0.0636 (17) | 0.0453 (14) | −0.0256 (13) | 0.0125 (12) | 0.0108 (12) |
O52 | 0.0533 (17) | 0.0445 (14) | 0.0728 (19) | −0.0192 (12) | 0.0193 (15) | 0.0005 (13) |
C53 | 0.0374 (17) | 0.0369 (16) | 0.0483 (18) | −0.0068 (13) | 0.0056 (14) | 0.0134 (14) |
C54 | 0.045 (2) | 0.054 (2) | 0.0432 (18) | −0.0159 (16) | 0.0091 (15) | 0.0086 (15) |
C55 | 0.0434 (19) | 0.0433 (17) | 0.0408 (17) | −0.0088 (14) | 0.0074 (14) | 0.0136 (14) |
C56 | 0.047 (2) | 0.059 (2) | 0.0396 (17) | −0.0201 (17) | 0.0069 (15) | 0.0102 (15) |
C57 | 0.0396 (17) | 0.0454 (18) | 0.0382 (16) | −0.0062 (14) | 0.0059 (13) | 0.0143 (14) |
O58 | 0.0527 (15) | 0.0540 (15) | 0.0405 (13) | −0.0148 (12) | 0.0032 (11) | 0.0140 (11) |
O59 | 0.0574 (18) | 0.083 (2) | 0.0423 (14) | −0.0352 (16) | 0.0057 (13) | 0.0184 (14) |
N1—C2 | 1.501 (4) | N25—C26 | 1.351 (4) |
O1—C1 | 1.255 (4) | C26—N27 | 1.312 (5) |
O2—C1 | 1.250 (4) | N27—C28 | 1.385 (4) |
C1—C2 | 1.538 (4) | N31—C32 | 1.490 (4) |
C2—C3 | 1.513 (4) | O31—C31 | 1.233 (4) |
C3—C4 | 1.498 (4) | O32—C31 | 1.267 (4) |
C4—C8 | 1.359 (4) | C31—C32 | 1.522 (4) |
C4—N5 | 1.374 (4) | C32—C33 | 1.537 (4) |
N5—C6 | 1.331 (4) | C33—C34 | 1.489 (4) |
C6—N7 | 1.322 (5) | C34—C38 | 1.355 (5) |
N7—C8 | 1.377 (4) | C34—N35 | 1.380 (4) |
N11—C12 | 1.483 (4) | N35—C36 | 1.341 (4) |
O11—C11 | 1.250 (4) | C36—N37 | 1.309 (5) |
O12—C11 | 1.250 (4) | N37—C38 | 1.379 (5) |
C11—C12 | 1.530 (4) | O41—C43 | 1.266 (5) |
C12—C13 | 1.531 (4) | O42—C43 | 1.247 (4) |
C13—C14 | 1.493 (4) | C43—C44 | 1.511 (5) |
C14—C18 | 1.359 (5) | C44—C45 | 1.528 (4) |
C14—N15 | 1.368 (4) | C45—C46 | 1.521 (4) |
N15—C16 | 1.340 (4) | C46—C47 | 1.512 (5) |
C16—N17 | 1.317 (5) | C47—O48 | 1.207 (4) |
N17—C18 | 1.378 (4) | C47—O49 | 1.317 (4) |
N21—C22 | 1.477 (4) | O51—C53 | 1.266 (5) |
O21—C21 | 1.236 (4) | O52—C53 | 1.239 (5) |
O22—C21 | 1.255 (4) | C53—C54 | 1.524 (5) |
C21—C22 | 1.537 (4) | C54—C55 | 1.512 (5) |
C22—C23 | 1.535 (4) | C55—C56 | 1.514 (5) |
C23—C24 | 1.497 (4) | C56—C57 | 1.504 (5) |
C24—C28 | 1.366 (5) | C57—O58 | 1.214 (5) |
C24—N25 | 1.372 (4) | C57—O59 | 1.298 (4) |
O2—C1—O1 | 126.8 (3) | N25—C24—C23 | 123.5 (3) |
O2—C1—C2 | 117.7 (3) | C26—N25—C24 | 107.5 (3) |
O1—C1—C2 | 115.5 (3) | N27—C26—N25 | 111.7 (3) |
N1—C2—C3 | 112.0 (2) | C26—N27—C28 | 105.4 (3) |
N1—C2—C1 | 107.8 (2) | C24—C28—N27 | 109.9 (3) |
C3—C2—C1 | 113.6 (2) | O31—C31—O32 | 124.5 (3) |
C4—C3—C2 | 112.1 (2) | O31—C31—C32 | 118.8 (3) |
C8—C4—N5 | 106.4 (3) | O32—C31—C32 | 116.7 (3) |
C8—C4—C3 | 132.9 (3) | N31—C32—C31 | 109.2 (2) |
N5—C4—C3 | 120.6 (3) | N31—C32—C33 | 109.2 (2) |
C6—N5—C4 | 108.7 (3) | C31—C32—C33 | 111.7 (2) |
N7—C6—N5 | 109.2 (3) | C34—C33—C32 | 114.3 (2) |
C6—N7—C8 | 108.2 (3) | C38—C34—N35 | 105.2 (3) |
C4—C8—N7 | 107.5 (3) | C38—C34—C33 | 131.8 (3) |
O11—C11—O12 | 126.5 (3) | N35—C34—C33 | 123.0 (3) |
O11—C11—C12 | 118.1 (3) | C36—N35—C34 | 107.7 (3) |
O12—C11—C12 | 115.4 (3) | N37—C36—N35 | 111.4 (3) |
N11—C12—C11 | 109.7 (2) | C36—N37—C38 | 105.6 (3) |
N11—C12—C13 | 111.3 (2) | C34—C38—N37 | 110.1 (3) |
C11—C12—C13 | 109.4 (2) | O42—C43—O41 | 123.4 (3) |
C14—C13—C12 | 115.0 (3) | O42—C43—C44 | 118.4 (3) |
C18—C14—N15 | 106.6 (3) | O41—C43—C44 | 118.2 (3) |
C18—C14—C13 | 130.1 (3) | C43—C44—C45 | 115.6 (3) |
N15—C14—C13 | 123.3 (3) | C46—C45—C44 | 112.8 (3) |
C16—N15—C14 | 108.4 (3) | C47—C46—C45 | 114.3 (3) |
N17—C16—N15 | 109.4 (3) | O48—C47—O49 | 122.2 (3) |
C16—N17—C18 | 107.9 (3) | O48—C47—C46 | 124.1 (3) |
C14—C18—N17 | 107.7 (3) | O49—C47—C46 | 113.8 (3) |
O21—C21—O22 | 125.4 (3) | O52—C53—O51 | 123.6 (3) |
O21—C21—C22 | 117.8 (3) | O52—C53—C54 | 118.8 (3) |
O22—C21—C22 | 116.7 (2) | O51—C53—C54 | 117.6 (3) |
N21—C22—C23 | 110.7 (2) | C55—C54—C53 | 114.8 (3) |
N21—C22—C21 | 110.6 (2) | C54—C55—C56 | 112.1 (3) |
C23—C22—C21 | 107.6 (2) | C57—C56—C55 | 115.0 (3) |
C24—C23—C22 | 117.4 (2) | O58—C57—O59 | 123.9 (3) |
C28—C24—N25 | 105.5 (3) | O58—C57—C56 | 124.4 (3) |
C28—C24—C23 | 130.8 (3) | O59—C57—C56 | 111.7 (3) |
O2—C1—C2—N1 | −155.4 (3) | O31—C31—C32—N31 | −34.1 (4) |
O1—C1—C2—N1 | 25.4 (3) | O32—C31—C32—N31 | 147.7 (3) |
O2—C1—C2—C3 | −30.6 (4) | O31—C31—C32—C33 | 86.8 (3) |
O1—C1—C2—C3 | 150.2 (3) | O32—C31—C32—C33 | −91.4 (3) |
N1—C2—C3—C4 | −61.0 (3) | N31—C32—C33—C34 | 177.3 (3) |
C1—C2—C3—C4 | 176.5 (2) | C31—C32—C33—C34 | 56.5 (4) |
C2—C3—C4—C8 | −12.1 (5) | C32—C33—C34—C38 | −108.5 (4) |
C2—C3—C4—N5 | 163.5 (3) | C32—C33—C34—N35 | 71.3 (4) |
C8—C4—N5—C6 | −0.5 (4) | C38—C34—N35—C36 | −0.1 (4) |
C3—C4—N5—C6 | −177.1 (3) | C33—C34—N35—C36 | −180.0 (3) |
C4—N5—C6—N7 | 0.4 (4) | C34—N35—C36—N37 | 0.4 (4) |
N5—C6—N7—C8 | −0.1 (4) | N35—C36—N37—C38 | −0.5 (4) |
N5—C4—C8—N7 | 0.4 (3) | N35—C34—C38—N37 | −0.2 (4) |
C3—C4—C8—N7 | 176.4 (3) | C33—C34—C38—N37 | 179.7 (3) |
C6—N7—C8—C4 | −0.2 (4) | C36—N37—C38—C34 | 0.4 (4) |
O11—C11—C12—N11 | 2.9 (4) | O42—C43—C44—C45 | 178.2 (3) |
O12—C11—C12—N11 | −176.6 (3) | O41—C43—C44—C45 | −0.6 (5) |
O11—C11—C12—C13 | 125.1 (3) | C43—C44—C45—C46 | −175.7 (3) |
O12—C11—C12—C13 | −54.4 (4) | C44—C45—C46—C47 | −178.2 (3) |
N11—C12—C13—C14 | −51.9 (4) | C45—C46—C47—O48 | −2.1 (5) |
C11—C12—C13—C14 | −173.2 (3) | C45—C46—C47—O49 | 178.5 (3) |
C12—C13—C14—C18 | 108.6 (4) | O52—C53—C54—C55 | 176.2 (4) |
C12—C13—C14—N15 | −73.0 (4) | O51—C53—C54—C55 | −5.3 (6) |
C18—C14—N15—C16 | 0.4 (3) | C53—C54—C55—C56 | 175.0 (4) |
C13—C14—N15—C16 | −178.4 (3) | C54—C55—C56—C57 | −179.7 (4) |
C14—N15—C16—N17 | −0.3 (4) | C55—C56—C57—O58 | −6.3 (6) |
N15—C16—N17—C18 | 0.2 (4) | C55—C56—C57—O59 | 174.4 (4) |
N15—C14—C18—N17 | −0.2 (3) | H1A—N1—C2—H2 | 123.2 |
C13—C14—C18—N17 | 178.4 (3) | H1B—N1—C2—C1 | 127.2 |
C16—N17—C18—C14 | 0.0 (4) | H1C—N1—C2—C3 | 121.5 |
O21—C21—C22—N21 | −30.7 (4) | H1A—N1—C2—C1 | 7.2 |
O22—C21—C22—N21 | 152.1 (3) | H1B—N1—C2—C3 | 1.5 |
O21—C21—C22—C23 | 90.2 (3) | H1C—N1—C2—H2 | 3.2 |
O22—C21—C22—C23 | −87.0 (3) | H1A—N1—C2—C3 | −118.5 |
N21—C22—C23—C24 | −64.3 (4) | H1B—N1—C2—H2 | −116.8 |
C21—C22—C23—C24 | 174.8 (3) | H1C—N1—C2—C1 | −112.8 |
C22—C23—C24—C28 | 118.7 (4) | H11A—N11—C12—H12 | −165.4 |
C22—C23—C24—N25 | −68.1 (4) | H11B—N11—C12—C11 | −164.3 |
C28—C24—N25—C26 | 1.0 (3) | H11C—N11—C12—C13 | −165.4 |
C23—C24—N25—C26 | −173.7 (3) | H21A—N21—C22—H22 | −164.3 |
C24—N25—C26—N27 | −0.7 (4) | H21B—N21—C22—C21 | −164.7 |
N25—C26—N27—C28 | 0.2 (4) | H21C—N21—C22—C23 | −163.8 |
N25—C24—C28—N27 | −0.9 (4) | H31A—N31—C32—H32 | −170.5 |
C23—C24—C28—N27 | 173.2 (3) | H31B—N31—C32—C31 | −169.3 |
C26—N27—C28—C24 | 0.5 (4) | H31C—N31—C32—C33 | −171.7 |
Experimental details
(I) | (A) | (B) | |
Crystal data | |||
Chemical formula | <C9N4H21O5> | <C11H19N3O7> | C34H52N12O16 |
Mr | 516.57 | 1221.17 | 884.88 |
Crystal system, space group | Monoclinic, C2 | Orthorhombic, P212121 | Triclinic, P1 |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 19.008 (3), 5.073 (2), 13.6723 (19) | 8.335 (1), 8.856 (1), 19.522 (2) | 5.791 (1), 13.110 (3), 14.360 (3) |
α, β, γ (°) | 90, 101.109 (13), 90 | 90, 90, 90 | 110.46 (2), 89.78 (1), 95.62 (2) |
V (Å3) | 1293.5 (6) | 1441.0 (3) | 1016.0 (4) |
Z | 2 | 4 | 2 |
Radiation type | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 0.92 | 1.01 | 0.99 |
Crystal size (mm) | 0.4 × 0.05 × 0.05 | 0.56 × 0.38 × 0.06 | 0.8 × 0.6 × 0.5 |
Data collection | |||
Diffractometer | CAD4 diffractometer | CAD4 diffractometer | CAD4 diffractometer |
Absorption correction | Empirical (North et al., 1968) North et al., 1968 | Cylinder (Dwiggins, 1975) Dwiggins JR Acta Cryst.(1975)A31,146-148 | Numerical (Dwiggins, 1975) Dwiggins JR Acta.Cryst 1975,A31,146 |
Tmin, Tmax | 0.955, 1.000 | 0.844, 0.848 | 0.604, 0.629 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1545, 1494, 1161 | 1609, 1609, 1295 | 6281, 4174, 4023 |
Rint | 0.033 | 0.000 | 0.031 |
(sin θ/λ)max (Å−1) | 0.626 | 0.626 | 0.627 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.158, 1.11 | 0.055, 0.144, 1.16 | 0.042, 0.124, 1.13 |
No. of reflections | 1494 | 1609 | 4174 |
No. of parameters | 170 | 199 | 566 |
No. of restraints | 2 | 1 | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 | 0.24, −0.29 | 0.33, −0.37 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Computer programs: CAD4, MolEN, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), ORTEP III, MSWORD, MS WORD, MS Word.
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