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The complexes of glutaric acid with L-arginine and L-histidine (two crystal forms) exhibit different stoichiometries and ionization states. The aggregation patterns in two of the crystals are remarkably similar to those observed earlier in similar structures, while the pattern in the remaining one has not been seen earlier. The variability in the ionization state and stoichiometry observed in amino acid-dicarboxylic acid complexes appears to represent subtle differences in the response of a molecule to the presence in its neighbourhood of another type of molecule. The glutaric acid molecules (or glutarate or semiglutarate ions) in their complexes and in other crystals favour a fully extended conformation, albeit with frequent departures from it. The change in the chirality of the component molecules in the complex could lead to drastic changes in the aggregation pattern; alternatively, the effects of the change are accommodated through small adjustments in essentially the same pattern.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101013684/de0013sup1.cif
Contains datablocks global, I, A, B

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013684/de0013Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013684/de0013Asup3.hkl
Contains datablock A

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101013684/de0013Bsup4.hkl
Contains datablock B

CCDC references: 179368; 179369; 179370

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(I) top
Crystal data top
<C9N4H21O5>F(000) = 556
Mr = 516.57Dx = 1.326 Mg m3
Monoclinic, C2Cu Kα radiation, λ = 1.54180 Å
a = 19.008 (3) ÅCell parameters from 25 reflections
b = 5.073 (2) Åθ = 18–30°
c = 13.6723 (19) ŵ = 0.92 mm1
β = 101.109 (13)°T = 293 K
V = 1293.5 (6) Å3Needle, colourless
Z = 20.4 × 0.05 × 0.05 mm
Data collection top
CAD4
diffractometer
1161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 74.8°, θmin = 3.3°
ω–2/q scansh = 523
Absorption correction: empirical (North et al., 1968)
North et al., 1968
k = 66
Tmin = 0.955, Tmax = 1.000l = 1716
1545 measured reflections2 standard reflections every 60 min
1494 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 1.11Δρmax = 0.23 e Å3
1494 reflectionsΔρmin = 0.23 e Å3
170 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0053 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map
Crystal data top
<C9N4H21O5>V = 1293.5 (6) Å3
Mr = 516.57Z = 2
Monoclinic, C2Cu Kα radiation
a = 19.008 (3) ŵ = 0.92 mm1
b = 5.073 (2) ÅT = 293 K
c = 13.6723 (19) Å0.4 × 0.05 × 0.05 mm
β = 101.109 (13)°
Data collection top
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 = 1.000Rint = 0.033
1545 measured reflections2 standard reflections every 60 min
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.23 e Å3
1494 reflectionsΔρmin = 0.23 e Å3
170 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.00235 (17)0.9908 (8)0.1336 (2)0.0397 (8)
H1C1.03180.95260.09230.060*
H1B1.02771.04720.19140.060*
H1A0.97201.11640.10680.060*
O10.90552 (14)0.7840 (7)0.02090 (18)0.0455 (8)
O20.91373 (17)0.3883 (7)0.0498 (2)0.0532 (9)
C10.9249 (2)0.6314 (9)0.0507 (3)0.0383 (9)
C20.96136 (19)0.7502 (10)0.1507 (3)0.0389 (9)
H20.99410.62030.18810.047*
C30.9056 (2)0.8325 (10)0.2122 (3)0.0474 (11)
H3A0.92990.92670.27080.057*
H3B0.87220.95420.17290.057*
C40.8631 (2)0.6061 (11)0.2458 (3)0.0498 (11)
H4A0.83650.51550.18780.060*
H4B0.89590.48080.28410.060*
C50.8117 (2)0.7062 (11)0.3087 (3)0.0525 (12)
H5A0.78880.55800.33480.063*
H5B0.83790.80540.36470.063*
N60.75720 (19)0.8740 (9)0.2502 (2)0.0523 (10)
H60.75020.85950.18640.063*
C70.7174 (2)1.0480 (11)0.2878 (3)0.0454 (11)
N80.72929 (19)1.0978 (10)0.3847 (2)0.0543 (11)
H8A0.70361.21290.40800.065*
H8B0.76261.01500.42440.065*
N90.6655 (2)1.1797 (11)0.2292 (3)0.0625 (13)
H9A0.64071.29390.25430.075*
H9B0.65681.15110.16600.075*
O110.64854 (18)0.4798 (10)0.4612 (2)0.0666 (11)
O120.58634 (18)0.5705 (11)0.3129 (2)0.0762 (14)
C130.5994 (2)0.5996 (11)0.4052 (3)0.0494 (11)
C140.5511 (2)0.7815 (13)0.4511 (3)0.0587 (13)
H14A0.52390.89330.39980.070*
H14B0.58010.89400.50040.070*
C150.50000.6198 (19)0.50000.0588 (18)
H15A0.526 (3)0.467 (14)0.549 (3)0.071*
OW0.72442 (17)0.7589 (9)0.0349 (2)0.0602 (9)
H1W0.673 (3)0.781 (14)0.006 (4)0.090*
H2W0.734 (3)0.571 (15)0.024 (4)0.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0399 (15)0.034 (2)0.0432 (15)0.0008 (15)0.0027 (11)0.0036 (16)
O10.0544 (15)0.0421 (19)0.0378 (12)0.0117 (15)0.0030 (11)0.0047 (14)
O20.0531 (16)0.0356 (19)0.0653 (19)0.0015 (15)0.0027 (13)0.0017 (16)
C10.0392 (17)0.032 (2)0.0438 (19)0.0011 (18)0.0088 (14)0.0058 (19)
C20.0410 (18)0.035 (2)0.0402 (17)0.0020 (19)0.0054 (13)0.0002 (19)
C30.054 (2)0.045 (3)0.0445 (19)0.001 (2)0.0146 (16)0.006 (2)
C40.057 (2)0.041 (3)0.055 (2)0.004 (2)0.0186 (18)0.004 (2)
C50.052 (2)0.054 (3)0.054 (2)0.002 (2)0.0152 (18)0.006 (2)
N60.0516 (18)0.063 (3)0.0418 (16)0.005 (2)0.0085 (14)0.0000 (18)
C70.0431 (19)0.052 (3)0.0414 (18)0.003 (2)0.0094 (14)0.002 (2)
N80.0532 (18)0.067 (3)0.0421 (16)0.015 (2)0.0074 (14)0.0005 (18)
N90.058 (2)0.082 (4)0.0442 (17)0.021 (2)0.0029 (15)0.003 (2)
O110.0608 (17)0.090 (3)0.0464 (15)0.014 (2)0.0026 (12)0.011 (2)
O120.068 (2)0.112 (4)0.0435 (15)0.013 (2)0.0010 (13)0.016 (2)
C130.0429 (19)0.060 (3)0.045 (2)0.006 (2)0.0069 (15)0.008 (2)
C140.061 (3)0.058 (3)0.061 (2)0.001 (3)0.021 (2)0.003 (3)
C150.060 (4)0.061 (5)0.061 (4)0.0000.025 (3)0.000
OW0.0531 (17)0.059 (2)0.0644 (18)0.004 (2)0.0010 (13)0.004 (2)
Geometric parameters (Å, º) top
N1—C21.491 (6)N6—C71.329 (6)
O1—C11.247 (5)C7—N81.325 (5)
O2—C11.251 (6)C7—N91.326 (6)
C1—C21.532 (5)O11—C131.246 (6)
C2—C31.533 (5)O12—C131.247 (5)
C3—C41.526 (7)C13—C141.519 (7)
C4—C51.508 (6)C14—C151.521 (7)
C5—N61.455 (6)C15—C14i1.521 (7)
O1—C1—O2125.5 (4)C7—N6—C5124.9 (3)
O1—C1—C2118.1 (4)N8—C7—N9118.2 (4)
O2—C1—C2116.3 (4)N8—C7—N6121.0 (4)
N1—C2—C1110.0 (3)N9—C7—N6120.9 (4)
N1—C2—C3107.5 (4)O11—C13—O12122.9 (5)
C1—C2—C3110.8 (3)O11—C13—C14119.0 (4)
C4—C3—C2115.0 (4)O12—C13—C14118.1 (4)
C5—C4—C3110.9 (4)C13—C14—C15110.0 (5)
N6—C5—C4110.7 (3)C14i—C15—C14114.7 (7)
O1—C1—C2—N131.3 (5)C5—N6—C7—N85.9 (7)
O2—C1—C2—N1152.5 (4)C5—N6—C7—N9175.3 (5)
O1—C1—C2—C387.4 (5)O11—C13—C14—C1573.6 (5)
O2—C1—C2—C388.8 (5)O12—C13—C14—C15104.0 (5)
N1—C2—C3—C4174.3 (3)C13—C14—C15—C14i179.8 (4)
C1—C2—C3—C465.4 (5)H1A—N1—C2—H2172.6
C2—C3—C4—C5177.9 (3)H1B—N1—C2—C1173.0
C3—C4—C5—N664.9 (5)H1C—N1—C2—C3173.7
C4—C5—N6—C7160.2 (5)O11—C13—C14—C1573.6 (5)
Symmetry code: (i) x+1, y, z+1.
(A) top
Crystal data top
<C11H19N3O7>Dx = 1.407 Mg m3
Mr = 1221.17Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 8.335 (1) Åθ = 10–30°
b = 8.856 (1) ŵ = 1.01 mm1
c = 19.522 (2) ÅT = 293 K
V = 1441.0 (3) Å3Needle, colourless
Z = 40.56 × 0.38 × 0.06 mm
F(000) = 648
Data collection top
CAD4
diffractometer
1295 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 74.9°, θmin = 4.5°
ω–2/q scansh = 09
Absorption correction: cylinder (Dwiggins, 1975)
Dwiggins JR Acta Cryst.(1975)A31,146-148
k = 011
Tmin = 0.844, Tmax = 0.848l = 024
1609 measured reflections3 standard reflections every 60 min
1609 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 1.16Δρmax = 0.24 e Å3
1609 reflectionsΔρmin = 0.29 e Å3
199 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.028 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map
Crystal data top
<C11H19N3O7>V = 1441.0 (3) Å3
Mr = 1221.17Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 8.335 (1) ŵ = 1.01 mm1
b = 8.856 (1) ÅT = 293 K
c = 19.522 (2) Å0.56 × 0.38 × 0.06 mm
Data collection top
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 = 0.848Rint = 0.000
1609 measured reflections3 standard reflections every 60 min
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.24 e Å3
1609 reflectionsΔρmin = 0.29 e Å3
199 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7051 (4)0.9085 (4)0.50718 (17)0.0532 (9)
O20.9273 (5)0.8547 (4)0.44986 (19)0.0631 (11)
N10.7349 (5)0.6924 (4)0.59850 (16)0.0380 (9)
H1C0.74500.78000.62090.057*
H1B0.75670.61670.62670.057*
H1A0.63490.68400.58300.057*
C10.8250 (6)0.8305 (4)0.4951 (2)0.0367 (10)
C20.8485 (6)0.6900 (4)0.5399 (2)0.0366 (10)
H20.95810.69120.55810.044*
C30.8258 (6)0.5446 (4)0.4981 (2)0.0386 (10)
H3A0.71440.53720.48410.046*
H3B0.89070.55070.45700.046*
C40.8701 (6)0.4062 (4)0.53638 (19)0.0348 (10)
N51.0285 (5)0.3733 (4)0.55244 (17)0.0379 (9)
H51.11050.42660.54100.045*
C61.0327 (7)0.2458 (5)0.5883 (2)0.0429 (11)
H61.12450.19930.60530.051*
N70.8853 (5)0.1969 (4)0.59576 (17)0.0404 (9)
H70.85790.11590.61710.048*
C80.7822 (6)0.2941 (5)0.5645 (2)0.0401 (10)
H80.67110.28500.56280.048*
O110.8000 (5)0.0486 (3)0.66912 (15)0.0499 (9)
O120.6558 (5)0.1515 (3)0.75151 (17)0.0592 (11)
C130.7153 (6)0.0394 (5)0.7220 (2)0.0404 (11)
C140.6840 (6)0.1155 (5)0.7516 (2)0.0433 (11)
H14A0.60370.10780.78740.052*
H14B0.64200.18100.71610.052*
C150.8354 (7)0.1842 (5)0.7810 (2)0.0449 (12)
H15A0.91340.19680.74450.054*
H15B0.88070.11550.81450.054*
C160.8047 (8)0.3367 (4)0.8148 (2)0.0484 (13)
H16A0.71370.32640.84550.058*
H16B0.89730.36230.84250.058*
C170.7721 (6)0.4652 (5)0.7668 (2)0.0406 (11)
O180.7879 (5)0.4615 (3)0.70578 (15)0.0593 (11)
O190.7252 (6)0.5867 (3)0.80052 (16)0.0605 (11)
H190.70360.65400.77320.091*
OW0.8968 (6)0.1499 (4)0.39960 (19)0.0595 (10)
H1W0.899 (9)0.138 (7)0.352 (3)0.089*
H2W0.897 (9)0.064 (8)0.414 (3)0.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.051 (2)0.0405 (16)0.068 (2)0.0145 (17)0.0090 (18)0.0228 (16)
O20.071 (3)0.053 (2)0.065 (2)0.0167 (19)0.021 (2)0.0304 (18)
N10.054 (2)0.0244 (14)0.0356 (16)0.0018 (17)0.0024 (17)0.0039 (14)
C10.048 (3)0.0243 (19)0.038 (2)0.0014 (18)0.006 (2)0.0042 (16)
C20.053 (3)0.0253 (18)0.0315 (18)0.001 (2)0.006 (2)0.0047 (16)
C30.058 (3)0.0285 (19)0.0294 (18)0.001 (2)0.003 (2)0.0007 (16)
C40.051 (3)0.0238 (17)0.0296 (18)0.002 (2)0.000 (2)0.0026 (15)
N50.046 (2)0.0249 (16)0.0423 (19)0.0007 (17)0.0036 (17)0.0045 (15)
C60.055 (3)0.030 (2)0.043 (2)0.005 (2)0.004 (2)0.0062 (19)
N70.060 (3)0.0222 (15)0.0390 (18)0.0060 (18)0.0061 (18)0.0060 (15)
C80.051 (3)0.030 (2)0.040 (2)0.003 (2)0.002 (2)0.0033 (17)
O110.082 (3)0.0223 (13)0.0449 (16)0.0039 (16)0.0140 (18)0.0025 (12)
O120.094 (3)0.0238 (14)0.0592 (19)0.0012 (18)0.026 (2)0.0058 (14)
C130.059 (3)0.0230 (19)0.039 (2)0.000 (2)0.001 (2)0.0012 (16)
C140.052 (3)0.025 (2)0.053 (2)0.0017 (19)0.004 (2)0.0024 (19)
C150.059 (3)0.027 (2)0.048 (2)0.007 (2)0.004 (2)0.0005 (18)
C160.080 (4)0.029 (2)0.036 (2)0.001 (2)0.007 (2)0.0020 (17)
C170.060 (3)0.0245 (19)0.038 (2)0.004 (2)0.003 (2)0.0029 (17)
O180.108 (3)0.0328 (15)0.0368 (16)0.004 (2)0.001 (2)0.0013 (13)
O190.109 (3)0.0277 (14)0.0451 (17)0.010 (2)0.003 (2)0.0039 (13)
OW0.079 (3)0.045 (2)0.055 (2)0.002 (2)0.003 (2)0.0101 (17)
Geometric parameters (Å, º) top
O1—C11.237 (5)N7—C81.361 (6)
O2—C11.247 (5)O11—C131.253 (5)
N1—C21.485 (5)O12—C131.251 (5)
C1—C21.533 (5)C13—C141.511 (6)
C2—C31.536 (5)C14—C151.514 (7)
C3—C41.482 (5)C15—C161.525 (6)
C4—C81.351 (6)C16—C171.499 (5)
C4—N51.388 (6)C17—O181.200 (5)
N5—C61.329 (5)C17—O191.320 (5)
C6—N71.311 (7)
O1—C1—O2126.2 (4)C6—N7—C8109.5 (4)
O1—C1—C2116.6 (4)C4—C8—N7107.8 (4)
O2—C1—C2117.2 (4)O12—C13—O11123.4 (4)
N1—C2—C1110.1 (4)O12—C13—C14118.4 (4)
N1—C2—C3110.2 (3)O11—C13—C14118.2 (4)
C1—C2—C3111.2 (3)C13—C14—C15111.4 (4)
C4—C3—C2113.3 (3)C14—C15—C16112.3 (4)
C8—C4—N5105.6 (4)C17—C16—C15115.6 (3)
C8—C4—C3132.7 (5)O18—C17—O19123.3 (4)
N5—C4—C3121.6 (4)O18—C17—C16125.5 (4)
C6—N5—C4108.8 (4)O19—C17—C16111.2 (3)
N7—C6—N5108.3 (4)
O1—C1—C2—N110.8 (5)N5—C4—C8—N70.5 (5)
O2—C1—C2—N1169.8 (4)C3—C4—C8—N7178.0 (4)
O1—C1—C2—C3111.6 (5)C6—N7—C8—C40.5 (5)
O2—C1—C2—C367.8 (5)O12—C13—C14—C15111.6 (5)
N1—C2—C3—C466.0 (5)O11—C13—C14—C1568.2 (6)
C1—C2—C3—C4171.7 (4)C13—C14—C15—C16176.7 (3)
C2—C3—C4—C8107.2 (5)C14—C15—C16—C1772.8 (6)
C2—C3—C4—N570.0 (5)C15—C16—C17—O189.8 (8)
C8—C4—N5—C60.4 (5)C15—C16—C17—O19171.3 (5)
C3—C4—N5—C6178.2 (4)H1A—N1—C2—H2175.2
C4—N5—C6—N70.0 (5)H1B—N1—C2—C1173.6
N5—C6—N7—C80.3 (5)H1C—N1—C2—C3176.7
(B) top
Crystal data top
C34H52N12O16Z = 2
Mr = 884.88F(000) = 468
Triclinic, P1Dx = 1.446 Mg m3
a = 5.791 (1) ÅCu Kα radiation, λ = 1.54180 Å
b = 13.110 (3) ÅCell parameters from 25 reflections
c = 14.360 (3) Åθ = 10–30°
α = 110.46 (2)°µ = 0.99 mm1
β = 89.78 (1)°T = 293 K
γ = 95.62 (2)°Platy, colourless
V = 1016.0 (4) Å30.8 × 0.6 × 0.5 mm
Data collection top
CAD4
diffractometer
4023 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 75.1°, θmin = 3.3°
ω–2/q scansh = 07
Absorption correction: numerical (Dwiggins, 1975)
Dwiggins JR Acta.Cryst 1975,A31,146
k = 1616
Tmin = 0.604, Tmax = 0.629l = 1717
6281 measured reflections3 standard reflections every 60 min
4174 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 1.13Δρmax = 0.33 e Å3
4174 reflectionsΔρmin = 0.37 e Å3
566 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0187 (17)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map
Crystal data top
C34H52N12O16γ = 95.62 (2)°
Mr = 884.88V = 1016.0 (4) Å3
Triclinic, P1Z = 2
a = 5.791 (1) ÅCu Kα radiation
b = 13.110 (3) ŵ = 0.99 mm1
c = 14.360 (3) ÅT = 293 K
α = 110.46 (2)°0.8 × 0.6 × 0.5 mm
β = 89.78 (1)°
Data collection top
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 = 0.629Rint = 0.031
6281 measured reflections3 standard reflections every 60 min
Refinement top
R[F2 > 2σ(F2)] = 0.0423 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.33 e Å3
4174 reflectionsΔρmin = 0.37 e Å3
566 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.1322 (4)0.0507 (2)0.39355 (19)0.0328 (5)
H1B1.00820.02650.35250.049*
H1A1.18670.11710.39510.049*
H1C1.09250.05380.45440.049*
O11.5593 (4)0.14124 (19)0.40499 (18)0.0421 (5)
O21.6890 (4)0.0052 (2)0.2905 (2)0.0448 (6)
C11.5420 (5)0.0424 (2)0.3496 (2)0.0312 (6)
C21.3162 (5)0.0259 (2)0.3577 (2)0.0286 (5)
H21.34280.05760.40870.034*
C31.2419 (5)0.1190 (3)0.2621 (2)0.0330 (6)
H3A1.21030.08930.21090.040*
H3B1.36780.16460.24050.040*
C41.0298 (5)0.1877 (2)0.2744 (2)0.0312 (6)
N50.9020 (5)0.2579 (2)0.1928 (2)0.0354 (5)
H50.93520.26940.13180.042*
C60.7183 (6)0.3050 (3)0.2238 (3)0.0401 (7)
H60.60530.35620.18280.048*
N70.7218 (5)0.2675 (2)0.3221 (2)0.0379 (6)
H70.62060.28610.35870.046*
C80.9156 (6)0.1936 (3)0.3556 (2)0.0357 (6)
H80.96030.15480.42160.043*
N110.6451 (4)0.1831 (2)0.20463 (19)0.0310 (5)
H11C0.61800.11940.21410.047*
H11B0.78940.21200.22530.047*
H11A0.62760.17220.14020.047*
O110.2110 (4)0.09818 (19)0.19774 (19)0.0418 (5)
O120.0773 (4)0.2554 (2)0.2891 (2)0.0502 (6)
C110.2348 (5)0.1981 (3)0.2481 (2)0.0311 (6)
C120.4788 (5)0.2589 (2)0.2617 (2)0.0289 (5)
H120.52520.28540.33240.035*
C130.4758 (5)0.3572 (3)0.2276 (3)0.0365 (6)
H13A0.40460.33200.16140.044*
H13B0.37870.40850.27160.044*
C140.7085 (6)0.4164 (2)0.2257 (2)0.0332 (6)
N150.8324 (5)0.4821 (2)0.3097 (2)0.0358 (5)
H150.79100.49380.36980.043*
C161.0293 (6)0.5250 (3)0.2824 (3)0.0394 (7)
H161.14330.57290.32570.047*
N171.0363 (5)0.4889 (2)0.1846 (2)0.0376 (6)
H171.14610.50520.15020.045*
C180.8364 (6)0.4204 (3)0.1473 (2)0.0366 (6)
H180.79620.38360.08040.044*
N211.0364 (4)0.1714 (2)0.91599 (18)0.0304 (5)
H21A1.02590.13110.85150.046*
H21C1.08550.24040.92360.046*
H21B0.89760.16890.94240.046*
O211.4886 (4)0.1694 (2)0.86203 (17)0.0451 (6)
O221.6074 (4)0.1685 (2)1.00806 (17)0.0406 (5)
C211.4536 (5)0.1594 (2)0.9435 (2)0.0296 (5)
C221.2027 (5)0.1280 (2)0.9666 (2)0.0289 (5)
H221.18260.15811.03860.035*
C231.1633 (5)0.0026 (3)0.9310 (3)0.0373 (6)
H23A1.17950.02540.85950.045*
H23B1.28660.02290.96000.045*
C240.9364 (5)0.0474 (2)0.9538 (2)0.0339 (6)
N250.8733 (5)0.0390 (2)1.0482 (2)0.0360 (5)
H250.94880.00031.10250.043*
C260.6709 (6)0.1026 (3)1.0402 (3)0.0385 (7)
H260.59290.11151.09410.046*
N270.5981 (5)0.1504 (2)0.9473 (2)0.0386 (6)
C280.7637 (6)0.1157 (3)0.8920 (3)0.0380 (7)
H280.75820.13600.82320.046*
N310.5204 (4)0.0351 (2)0.66261 (19)0.0330 (5)
H31C0.53160.03650.64410.050*
H31B0.38430.04600.64110.050*
H31A0.53090.06490.72860.050*
O310.9685 (4)0.0336 (2)0.71857 (16)0.0418 (5)
O321.0943 (4)0.0404 (2)0.57494 (18)0.0438 (5)
C310.9412 (5)0.0497 (2)0.6399 (2)0.0298 (5)
C320.7118 (5)0.0866 (2)0.6191 (2)0.0296 (6)
H320.68420.06260.54700.036*
C330.7135 (6)0.2117 (3)0.6634 (3)0.0381 (7)
H33A0.56650.23150.64630.046*
H33B0.72600.23450.73530.046*
C340.9050 (6)0.2729 (3)0.6289 (2)0.0338 (6)
N350.9110 (5)0.2754 (2)0.5337 (2)0.0383 (6)
H350.80870.24310.48670.046*
C361.1052 (7)0.3371 (3)0.5276 (3)0.0430 (7)
H361.14870.35180.47070.052*
N371.2258 (6)0.3741 (3)0.6117 (2)0.0465 (7)
C381.1006 (6)0.3344 (3)0.6758 (2)0.0424 (7)
H381.14410.34800.74170.051*
O410.3625 (5)0.5231 (3)1.0737 (2)0.0558 (7)
O420.1769 (5)0.3925 (2)0.9464 (2)0.0571 (7)
C430.3421 (6)0.4642 (3)0.9825 (3)0.0385 (7)
C440.5250 (6)0.4836 (3)0.9135 (3)0.0446 (8)
H44A0.44910.50050.86140.053*
H44B0.59510.41610.88220.053*
C450.7182 (6)0.5750 (3)0.9622 (2)0.0367 (6)
H45A0.64920.64190.99740.044*
H45B0.80380.55581.01050.044*
C460.8861 (6)0.5959 (3)0.8875 (3)0.0417 (7)
H46A0.95030.52810.85080.050*
H46B0.80030.61690.84030.050*
C471.0839 (5)0.6835 (2)0.9334 (2)0.0350 (6)
O481.1069 (5)0.7359 (2)1.02118 (19)0.0497 (6)
O491.2310 (5)0.6991 (2)0.8683 (2)0.0506 (6)
H491.33720.74520.89750.076*
O511.4102 (5)0.6831 (3)0.4302 (2)0.0590 (8)
O521.5795 (5)0.8291 (2)0.5483 (3)0.0640 (9)
C531.4250 (6)0.7517 (3)0.5182 (3)0.0421 (7)
C541.2452 (7)0.7355 (3)0.5909 (3)0.0511 (9)
H54A1.32430.72130.64390.061*
H54B1.17440.80310.62060.061*
C551.0551 (7)0.6435 (3)0.5456 (3)0.0438 (8)
H55A1.12460.57660.51120.053*
H55B0.96520.66040.49700.053*
C560.8948 (7)0.6253 (4)0.6232 (3)0.0520 (9)
H56A0.98670.60960.67190.062*
H56B0.82680.69280.65740.062*
C570.7019 (6)0.5345 (3)0.5834 (3)0.0420 (7)
O580.6596 (5)0.4840 (2)0.49561 (19)0.0512 (6)
O590.5838 (6)0.5172 (3)0.6544 (2)0.0648 (9)
H590.46640.47590.63070.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0284 (12)0.0358 (12)0.0312 (12)0.0013 (9)0.0036 (9)0.0095 (10)
O10.0392 (12)0.0397 (12)0.0423 (12)0.0127 (9)0.0042 (10)0.0124 (10)
O20.0257 (11)0.0527 (14)0.0559 (14)0.0006 (9)0.0066 (10)0.0203 (11)
C10.0261 (13)0.0377 (14)0.0324 (14)0.0059 (11)0.0037 (11)0.0178 (11)
C20.0257 (13)0.0318 (13)0.0295 (13)0.0018 (10)0.0002 (10)0.0133 (11)
C30.0289 (14)0.0342 (14)0.0325 (14)0.0045 (11)0.0053 (11)0.0097 (12)
C40.0323 (15)0.0270 (13)0.0333 (14)0.0023 (11)0.0028 (11)0.0106 (11)
N50.0359 (13)0.0333 (12)0.0328 (13)0.0041 (10)0.0022 (10)0.0084 (10)
C60.0369 (16)0.0343 (16)0.0437 (17)0.0075 (12)0.0013 (13)0.0098 (13)
N70.0343 (14)0.0335 (13)0.0437 (14)0.0056 (10)0.0068 (11)0.0131 (11)
C80.0365 (16)0.0330 (14)0.0350 (14)0.0066 (12)0.0024 (12)0.0114 (12)
N110.0267 (12)0.0332 (12)0.0329 (12)0.0017 (9)0.0034 (9)0.0125 (9)
O110.0352 (11)0.0382 (12)0.0474 (13)0.0102 (9)0.0002 (9)0.0128 (10)
O120.0251 (11)0.0568 (15)0.0568 (15)0.0001 (10)0.0075 (10)0.0064 (12)
C110.0268 (13)0.0391 (15)0.0267 (12)0.0031 (11)0.0004 (10)0.0125 (11)
C120.0246 (12)0.0332 (13)0.0274 (12)0.0006 (10)0.0011 (10)0.0095 (10)
C130.0313 (15)0.0353 (15)0.0448 (16)0.0004 (12)0.0015 (12)0.0171 (13)
C140.0343 (15)0.0255 (13)0.0405 (15)0.0003 (11)0.0029 (12)0.0131 (11)
N150.0363 (14)0.0312 (12)0.0377 (13)0.0018 (10)0.0034 (11)0.0107 (10)
C160.0361 (16)0.0316 (14)0.0469 (18)0.0043 (12)0.0031 (13)0.0113 (13)
N170.0333 (13)0.0336 (13)0.0463 (15)0.0027 (10)0.0054 (11)0.0161 (11)
C180.0382 (16)0.0322 (14)0.0381 (15)0.0017 (12)0.0034 (13)0.0120 (12)
N210.0257 (11)0.0326 (12)0.0321 (12)0.0010 (9)0.0022 (9)0.0114 (9)
O210.0330 (11)0.0695 (16)0.0339 (11)0.0038 (10)0.0065 (9)0.0222 (11)
O220.0245 (10)0.0636 (15)0.0333 (10)0.0008 (9)0.0006 (8)0.0178 (10)
C210.0232 (12)0.0335 (13)0.0274 (13)0.0021 (10)0.0031 (10)0.0064 (10)
C220.0237 (13)0.0345 (14)0.0263 (12)0.0029 (10)0.0026 (10)0.0095 (10)
C230.0271 (14)0.0333 (15)0.0519 (18)0.0018 (11)0.0085 (12)0.0157 (13)
C240.0290 (14)0.0293 (13)0.0422 (16)0.0002 (11)0.0033 (12)0.0121 (12)
N250.0325 (13)0.0346 (13)0.0388 (13)0.0017 (10)0.0000 (10)0.0118 (10)
C260.0355 (16)0.0369 (15)0.0451 (17)0.0003 (12)0.0083 (13)0.0180 (13)
N270.0308 (13)0.0333 (13)0.0496 (15)0.0043 (10)0.0028 (11)0.0139 (11)
C280.0364 (16)0.0362 (15)0.0390 (15)0.0009 (13)0.0033 (12)0.0115 (12)
N310.0260 (12)0.0383 (13)0.0333 (12)0.0040 (9)0.0030 (9)0.0126 (10)
O310.0400 (12)0.0582 (14)0.0290 (10)0.0074 (10)0.0003 (9)0.0169 (10)
O320.0266 (11)0.0695 (16)0.0380 (11)0.0075 (10)0.0095 (9)0.0219 (11)
C310.0251 (12)0.0354 (14)0.0262 (12)0.0003 (10)0.0003 (10)0.0082 (10)
C320.0238 (13)0.0356 (14)0.0273 (12)0.0030 (10)0.0030 (10)0.0101 (11)
C330.0328 (15)0.0361 (15)0.0460 (17)0.0037 (12)0.0105 (13)0.0150 (13)
C340.0346 (15)0.0322 (14)0.0343 (14)0.0004 (11)0.0010 (11)0.0120 (11)
N350.0408 (14)0.0345 (13)0.0365 (13)0.0065 (11)0.0028 (11)0.0112 (11)
C360.0480 (19)0.0375 (16)0.0409 (17)0.0061 (13)0.0078 (14)0.0134 (13)
N370.0438 (16)0.0446 (15)0.0453 (15)0.0130 (12)0.0038 (13)0.0131 (12)
C380.0392 (17)0.0469 (18)0.0351 (15)0.0068 (14)0.0004 (13)0.0098 (13)
O410.0436 (14)0.0689 (18)0.0446 (14)0.0248 (13)0.0047 (11)0.0151 (13)
O420.0447 (15)0.0421 (13)0.0728 (19)0.0178 (11)0.0027 (13)0.0117 (13)
C430.0334 (15)0.0315 (14)0.0498 (18)0.0041 (12)0.0009 (13)0.0151 (13)
C440.0416 (18)0.0384 (16)0.0444 (17)0.0105 (14)0.0048 (14)0.0068 (13)
C450.0372 (16)0.0325 (14)0.0371 (15)0.0057 (12)0.0029 (12)0.0104 (12)
C460.0395 (17)0.0415 (17)0.0378 (15)0.0077 (13)0.0068 (13)0.0093 (13)
C470.0322 (15)0.0341 (15)0.0376 (15)0.0005 (12)0.0066 (12)0.0121 (12)
O480.0493 (15)0.0530 (14)0.0366 (12)0.0165 (11)0.0052 (11)0.0088 (11)
O490.0439 (14)0.0543 (15)0.0426 (13)0.0162 (11)0.0108 (11)0.0090 (11)
O510.0546 (16)0.0636 (17)0.0453 (14)0.0256 (13)0.0125 (12)0.0108 (12)
O520.0533 (17)0.0445 (14)0.0728 (19)0.0192 (12)0.0193 (15)0.0005 (13)
C530.0374 (17)0.0369 (16)0.0483 (18)0.0068 (13)0.0056 (14)0.0134 (14)
C540.045 (2)0.054 (2)0.0432 (18)0.0159 (16)0.0091 (15)0.0086 (15)
C550.0434 (19)0.0433 (17)0.0408 (17)0.0088 (14)0.0074 (14)0.0136 (14)
C560.047 (2)0.059 (2)0.0396 (17)0.0201 (17)0.0069 (15)0.0102 (15)
C570.0396 (17)0.0454 (18)0.0382 (16)0.0062 (14)0.0059 (13)0.0143 (14)
O580.0527 (15)0.0540 (15)0.0405 (13)0.0148 (12)0.0032 (11)0.0140 (11)
O590.0574 (18)0.083 (2)0.0423 (14)0.0352 (16)0.0057 (13)0.0184 (14)
Geometric parameters (Å, º) top
N1—C21.501 (4)N25—C261.351 (4)
O1—C11.255 (4)C26—N271.312 (5)
O2—C11.250 (4)N27—C281.385 (4)
C1—C21.538 (4)N31—C321.490 (4)
C2—C31.513 (4)O31—C311.233 (4)
C3—C41.498 (4)O32—C311.267 (4)
C4—C81.359 (4)C31—C321.522 (4)
C4—N51.374 (4)C32—C331.537 (4)
N5—C61.331 (4)C33—C341.489 (4)
C6—N71.322 (5)C34—C381.355 (5)
N7—C81.377 (4)C34—N351.380 (4)
N11—C121.483 (4)N35—C361.341 (4)
O11—C111.250 (4)C36—N371.309 (5)
O12—C111.250 (4)N37—C381.379 (5)
C11—C121.530 (4)O41—C431.266 (5)
C12—C131.531 (4)O42—C431.247 (4)
C13—C141.493 (4)C43—C441.511 (5)
C14—C181.359 (5)C44—C451.528 (4)
C14—N151.368 (4)C45—C461.521 (4)
N15—C161.340 (4)C46—C471.512 (5)
C16—N171.317 (5)C47—O481.207 (4)
N17—C181.378 (4)C47—O491.317 (4)
N21—C221.477 (4)O51—C531.266 (5)
O21—C211.236 (4)O52—C531.239 (5)
O22—C211.255 (4)C53—C541.524 (5)
C21—C221.537 (4)C54—C551.512 (5)
C22—C231.535 (4)C55—C561.514 (5)
C23—C241.497 (4)C56—C571.504 (5)
C24—C281.366 (5)C57—O581.214 (5)
C24—N251.372 (4)C57—O591.298 (4)
O2—C1—O1126.8 (3)N25—C24—C23123.5 (3)
O2—C1—C2117.7 (3)C26—N25—C24107.5 (3)
O1—C1—C2115.5 (3)N27—C26—N25111.7 (3)
N1—C2—C3112.0 (2)C26—N27—C28105.4 (3)
N1—C2—C1107.8 (2)C24—C28—N27109.9 (3)
C3—C2—C1113.6 (2)O31—C31—O32124.5 (3)
C4—C3—C2112.1 (2)O31—C31—C32118.8 (3)
C8—C4—N5106.4 (3)O32—C31—C32116.7 (3)
C8—C4—C3132.9 (3)N31—C32—C31109.2 (2)
N5—C4—C3120.6 (3)N31—C32—C33109.2 (2)
C6—N5—C4108.7 (3)C31—C32—C33111.7 (2)
N7—C6—N5109.2 (3)C34—C33—C32114.3 (2)
C6—N7—C8108.2 (3)C38—C34—N35105.2 (3)
C4—C8—N7107.5 (3)C38—C34—C33131.8 (3)
O11—C11—O12126.5 (3)N35—C34—C33123.0 (3)
O11—C11—C12118.1 (3)C36—N35—C34107.7 (3)
O12—C11—C12115.4 (3)N37—C36—N35111.4 (3)
N11—C12—C11109.7 (2)C36—N37—C38105.6 (3)
N11—C12—C13111.3 (2)C34—C38—N37110.1 (3)
C11—C12—C13109.4 (2)O42—C43—O41123.4 (3)
C14—C13—C12115.0 (3)O42—C43—C44118.4 (3)
C18—C14—N15106.6 (3)O41—C43—C44118.2 (3)
C18—C14—C13130.1 (3)C43—C44—C45115.6 (3)
N15—C14—C13123.3 (3)C46—C45—C44112.8 (3)
C16—N15—C14108.4 (3)C47—C46—C45114.3 (3)
N17—C16—N15109.4 (3)O48—C47—O49122.2 (3)
C16—N17—C18107.9 (3)O48—C47—C46124.1 (3)
C14—C18—N17107.7 (3)O49—C47—C46113.8 (3)
O21—C21—O22125.4 (3)O52—C53—O51123.6 (3)
O21—C21—C22117.8 (3)O52—C53—C54118.8 (3)
O22—C21—C22116.7 (2)O51—C53—C54117.6 (3)
N21—C22—C23110.7 (2)C55—C54—C53114.8 (3)
N21—C22—C21110.6 (2)C54—C55—C56112.1 (3)
C23—C22—C21107.6 (2)C57—C56—C55115.0 (3)
C24—C23—C22117.4 (2)O58—C57—O59123.9 (3)
C28—C24—N25105.5 (3)O58—C57—C56124.4 (3)
C28—C24—C23130.8 (3)O59—C57—C56111.7 (3)
O2—C1—C2—N1155.4 (3)O31—C31—C32—N3134.1 (4)
O1—C1—C2—N125.4 (3)O32—C31—C32—N31147.7 (3)
O2—C1—C2—C330.6 (4)O31—C31—C32—C3386.8 (3)
O1—C1—C2—C3150.2 (3)O32—C31—C32—C3391.4 (3)
N1—C2—C3—C461.0 (3)N31—C32—C33—C34177.3 (3)
C1—C2—C3—C4176.5 (2)C31—C32—C33—C3456.5 (4)
C2—C3—C4—C812.1 (5)C32—C33—C34—C38108.5 (4)
C2—C3—C4—N5163.5 (3)C32—C33—C34—N3571.3 (4)
C8—C4—N5—C60.5 (4)C38—C34—N35—C360.1 (4)
C3—C4—N5—C6177.1 (3)C33—C34—N35—C36180.0 (3)
C4—N5—C6—N70.4 (4)C34—N35—C36—N370.4 (4)
N5—C6—N7—C80.1 (4)N35—C36—N37—C380.5 (4)
N5—C4—C8—N70.4 (3)N35—C34—C38—N370.2 (4)
C3—C4—C8—N7176.4 (3)C33—C34—C38—N37179.7 (3)
C6—N7—C8—C40.2 (4)C36—N37—C38—C340.4 (4)
O11—C11—C12—N112.9 (4)O42—C43—C44—C45178.2 (3)
O12—C11—C12—N11176.6 (3)O41—C43—C44—C450.6 (5)
O11—C11—C12—C13125.1 (3)C43—C44—C45—C46175.7 (3)
O12—C11—C12—C1354.4 (4)C44—C45—C46—C47178.2 (3)
N11—C12—C13—C1451.9 (4)C45—C46—C47—O482.1 (5)
C11—C12—C13—C14173.2 (3)C45—C46—C47—O49178.5 (3)
C12—C13—C14—C18108.6 (4)O52—C53—C54—C55176.2 (4)
C12—C13—C14—N1573.0 (4)O51—C53—C54—C555.3 (6)
C18—C14—N15—C160.4 (3)C53—C54—C55—C56175.0 (4)
C13—C14—N15—C16178.4 (3)C54—C55—C56—C57179.7 (4)
C14—N15—C16—N170.3 (4)C55—C56—C57—O586.3 (6)
N15—C16—N17—C180.2 (4)C55—C56—C57—O59174.4 (4)
N15—C14—C18—N170.2 (3)H1A—N1—C2—H2123.2
C13—C14—C18—N17178.4 (3)H1B—N1—C2—C1127.2
C16—N17—C18—C140.0 (4)H1C—N1—C2—C3121.5
O21—C21—C22—N2130.7 (4)H1A—N1—C2—C17.2
O22—C21—C22—N21152.1 (3)H1B—N1—C2—C31.5
O21—C21—C22—C2390.2 (3)H1C—N1—C2—H23.2
O22—C21—C22—C2387.0 (3)H1A—N1—C2—C3118.5
N21—C22—C23—C2464.3 (4)H1B—N1—C2—H2116.8
C21—C22—C23—C24174.8 (3)H1C—N1—C2—C1112.8
C22—C23—C24—C28118.7 (4)H11A—N11—C12—H12165.4
C22—C23—C24—N2568.1 (4)H11B—N11—C12—C11164.3
C28—C24—N25—C261.0 (3)H11C—N11—C12—C13165.4
C23—C24—N25—C26173.7 (3)H21A—N21—C22—H22164.3
C24—N25—C26—N270.7 (4)H21B—N21—C22—C21164.7
N25—C26—N27—C280.2 (4)H21C—N21—C22—C23163.8
N25—C24—C28—N270.9 (4)H31A—N31—C32—H32170.5
C23—C24—C28—N27173.2 (3)H31B—N31—C32—C31169.3
C26—N27—C28—C240.5 (4)H31C—N31—C32—C33171.7

Experimental details

(I)(A)(B)
Crystal data
Chemical formula<C9N4H21O5><C11H19N3O7>C34H52N12O16
Mr516.571221.17884.88
Crystal system, space groupMonoclinic, C2Orthorhombic, P212121Triclinic, P1
Temperature (K)293293293
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), 9090, 90, 90110.46 (2), 89.78 (1), 95.62 (2)
V3)1293.5 (6)1441.0 (3)1016.0 (4)
Z242
Radiation typeCu KαCu KαCu Kα
µ (mm1)0.921.010.99
Crystal size (mm)0.4 × 0.05 × 0.050.56 × 0.38 × 0.060.8 × 0.6 × 0.5
Data collection
DiffractometerCAD4
diffractometer
CAD4
diffractometer
CAD4
diffractometer
Absorption correctionEmpirical (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, Tmax0.955, 1.0000.844, 0.8480.604, 0.629
No. of measured, independent and
observed [I > 2σ(I)] reflections
1545, 1494, 1161 1609, 1609, 1295 6281, 4174, 4023
Rint0.0330.0000.031
(sin θ/λ)max1)0.6260.6260.627
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 reflections149416094174
No. of parameters170199566
No. of restraints213
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.230.24, 0.290.33, 0.37
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack 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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