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The crystal structures of six nitrotoluene derivatives, synthesized by Wilhelm Koerner about a century ago and retrieved from a depository at the University of Milano, were determined. The correct assignment of molecular structures is verified. The geometry of the nitro groups and factors affecting the orientation of nitro groups with respect to the benzene ring are discussed, also using an auxiliary set of crystal structures retrieved from the Cambridge Structural Database. The crystal packings have been analyzed, and lattice energies have been calculated by atom-atom potential methods and by the newly proposed Pixel method. This method allows a more complete description of intermolecular potentials in terms of the interaction between molecular electron densities and separate Coulombic, polarization, dispersion and overlap repulsion energies. Lattice vibrations and external entropies were calculated by lattice-dynamical procedures. The results of the Pixel energy calculations allow a reliable, quantitative assessment of the relative importance of stacking interactions and hydrogen bonding in the rationalization of the recognition modes of nitrobenzene derivatives, which is impossible to attain using only qualitative atom- atom geometry concepts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104014466/na5014sup1.cif
Contains datablocks K15, K19, K20, K6, K12, K14

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k19sup3.fcf
Contains datablock k19

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k15sup2.fcf
Original version: contains datablock k15

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k15sup12.fcf
Corrected version supplied by the author on 16 January 2012: contains datablock k15

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k20sup4.fcf
Original version: contains datablock k20

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k20sup13.fcf
Corrected version supplied by the author on 16 January 2012: contains datablock k20

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014gave6sup5.fcf
Original version: contains datablock gave6

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014gave6sup9.fcf
Corrected version supplied by the author on 16 January 2012: contains datablock gave6

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k12sup6.fcf
Original version: contains datablock k12

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k12sup10.fcf
Corrected version supplied by the author on 16 January 2012: contains datablock k12

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014466/na5014k14sup7.fcf
Original version: contains datablock k14

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Corrected version supplied by the author on 16 January 2012: contains datablock k14

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Supplementary material

CCDC references: 255121; 255122; 255123; 255124; 255125; 255126

Computing details top

For all compounds, program(s) used to solve structure: SIR2000 (Burla et al., 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL (Keller, 1993).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
[Figure 13]
[Figure 14]
[Figure 15]
[Figure 16]
(K15) top
Crystal data top
C8H6BrIN2O3Z = 2
Mr = 384.96F(000) = 360
Triclinic, P1Dx = 2.326 Mg m3
a = 4.797 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.673 (2) ÅCell parameters from 3296 reflections
c = 15.654 (4) Åθ = 2–25°
α = 96.98 (2)°µ = 6.54 mm1
β = 97.03 (2)°T = 293 K
γ = 103.34 (2)°Column, yellow
V = 549.7 (3) Å30.3 × 0.25 × 0.15 mm
Data collection top
SMART
diffractometer
1947 independent reflections
Graphite monochromatorRint = 0.034
ω–scanθmax = 25°, θmin = 2°
Absorption correction: SADABS
?
h = 55
Tmin = 0.62, Tmax = 1k = 99
4680 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.068P)2]
where P = (Fo2 + 2Fc2)/3
1947 reflections(Δ/σ)max = 0.013
136 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 1.48 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C8H6BrIN2O3γ = 103.34 (2)°
Mr = 384.96V = 549.7 (3) Å3
Triclinic, P1Z = 2
a = 4.797 (2) ÅMo Kα radiation
b = 7.673 (2) ŵ = 6.54 mm1
c = 15.654 (4) ÅT = 293 K
α = 96.98 (2)°0.3 × 0.25 × 0.15 mm
β = 97.03 (2)°
Data collection top
SMART
diffractometer
4680 measured reflections
Absorption correction: SADABS
?
1947 independent reflections
Tmin = 0.62, Tmax = 1Rint = 0.034
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
1947 reflectionsΔρmax = 0.59 e Å3
136 parametersΔρmin = 1.48 e Å3
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
C10.6105 (9)0.2304 (6)0.8716 (3)0.0373 (9)
C20.4599 (9)0.3601 (6)0.8553 (3)0.0397 (9)
H20.43850.44190.90150.048*
C30.3410 (9)0.3694 (6)0.7715 (3)0.0329 (8)
C40.3696 (8)0.2484 (6)0.7009 (3)0.0323 (8)
C50.5191 (9)0.1194 (6)0.7170 (3)0.0357 (9)
H50.54080.03740.6710.043*
C60.6372 (9)0.1110 (6)0.8013 (3)0.0349 (9)
Br0.78062 (14)0.23819 (8)0.98720 (3)0.0599 (2)
I0.13937 (5)0.57939 (3)0.753902 (18)0.04235 (17)
N1A0.2506 (7)0.2556 (5)0.6152 (2)0.0373 (8)
H1A0.07470.26530.60590.045*
C1A0.3950 (9)0.2481 (6)0.5465 (3)0.0396 (10)
O1A0.6424 (7)0.2332 (6)0.5535 (2)0.0613 (10)
C2A0.2284 (11)0.2573 (9)0.4603 (3)0.0563 (14)
H2A10.03770.26890.4680.084*
H2A20.21330.14860.42070.084*
H2A30.32760.36020.43710.084*
N1N0.7909 (8)0.0324 (5)0.8097 (2)0.0426 (9)
O1N0.7954 (11)0.0982 (6)0.8770 (3)0.0794 (13)
O2N0.8902 (8)0.0871 (5)0.7474 (2)0.0584 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.042 (2)0.039 (2)0.032 (2)0.0129 (18)0.0020 (16)0.0085 (17)
C20.044 (2)0.039 (2)0.039 (2)0.0148 (18)0.0111 (18)0.0029 (18)
C30.034 (2)0.033 (2)0.035 (2)0.0139 (16)0.0064 (16)0.0048 (17)
C40.0295 (19)0.035 (2)0.0343 (19)0.0140 (16)0.0015 (15)0.0050 (16)
C50.040 (2)0.034 (2)0.036 (2)0.0187 (18)0.0044 (17)0.0001 (17)
C60.034 (2)0.033 (2)0.042 (2)0.0149 (17)0.0052 (17)0.0094 (17)
Br0.0866 (4)0.0599 (4)0.0334 (3)0.0273 (3)0.0056 (3)0.0061 (2)
I0.0431 (2)0.0368 (2)0.0510 (2)0.02080 (15)0.00412 (15)0.00378 (15)
N1A0.0345 (17)0.046 (2)0.0350 (18)0.0211 (16)0.0007 (14)0.0043 (15)
C1A0.036 (2)0.046 (3)0.038 (2)0.0132 (19)0.0047 (18)0.0053 (19)
O1A0.0428 (18)0.104 (3)0.0493 (19)0.0368 (19)0.0120 (15)0.0182 (19)
C2A0.053 (3)0.087 (4)0.035 (2)0.027 (3)0.006 (2)0.014 (2)
N1N0.046 (2)0.040 (2)0.044 (2)0.0193 (17)0.0031 (17)0.0089 (17)
O1N0.124 (4)0.081 (3)0.052 (2)0.065 (3)0.002 (2)0.018 (2)
O2N0.076 (3)0.059 (3)0.059 (2)0.045 (2)0.022 (2)0.0152 (19)
Geometric parameters (Å, º) top
C1—C61.382 (6)C5—C61.385 (6)
C1—C21.387 (6)C6—N1N1.469 (5)
C1—Br1.881 (4)N1A—C1A1.352 (6)
C2—C31.383 (6)C1A—O1A1.211 (5)
C3—C41.395 (6)C1A—C2A1.499 (6)
C3—I2.090 (4)N1N—O2N1.209 (5)
C4—C51.379 (6)N1N—O1N1.222 (5)
C4—N1A1.405 (5)
C6—C1—C2117.8 (4)C1—C6—C5121.6 (4)
C6—C1—Br124.7 (3)C1—C6—N1N123.2 (4)
C2—C1—Br117.4 (3)C5—C6—N1N115.2 (4)
C3—C2—C1121.0 (4)C1A—N1A—C4124.1 (3)
C2—C3—C4120.8 (4)O1A—C1A—N1A122.4 (4)
C2—C3—I117.6 (3)O1A—C1A—C2A121.9 (4)
C4—C3—I121.5 (3)N1A—C1A—C2A115.8 (4)
C5—C4—C3118.3 (4)O2N—N1N—O1N123.4 (4)
C5—C4—N1A120.0 (4)O2N—N1N—C6118.0 (3)
C3—C4—N1A121.7 (4)O1N—N1N—C6118.5 (4)
C4—C5—C6120.5 (4)
(K19) top
Crystal data top
C7H5N3O6F(000) = 464
Mr = 227.14Dx = 1.548 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 13.644 (1) ÅCell parameters from 837 reflections
b = 9.550 (1) Åθ = 2–22°
c = 8.754 (1) ŵ = 0.14 mm1
β = 121.31 (2)°T = 293 K
V = 974.53 (17) Å3Block, very light yellow
Z = 40.36 × 0.3 × 0.26 mm
Data collection top
SMART
diffractometer
763 independent reflections
Graphite monochromatorRint = 0.032
ω–scanθmax = 24°, θmin = 2°
Absorption correction: SADABS
?
h = 1513
Tmin = 0.79, Tmax = 1k = 1010
2636 measured reflectionsl = 89
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 0.81 w = 1/[σ2(Fo2) + (0.1341P)2 + 0.2249P]
where P = (Fo2 + 2Fc2)/3
763 reflections(Δ/σ)max = 0.004
75 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C7H5N3O6V = 974.53 (17) Å3
Mr = 227.14Z = 4
Monoclinic, C2/cMo Kα radiation
a = 13.644 (1) ŵ = 0.14 mm1
b = 9.550 (1) ÅT = 293 K
c = 8.754 (1) Å0.36 × 0.3 × 0.26 mm
β = 121.31 (2)°
Data collection top
SMART
diffractometer
763 independent reflections
Absorption correction: SADABS
?
Rint = 0.032
Tmin = 0.79, Tmax = 1θmax = 24°
2636 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 0.81Δρmax = 0.15 e Å3
763 reflectionsΔρmin = 0.15 e Å3
75 parameters
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*/UeqOcc. (<1)
C10.50.6741 (3)0.250.0489 (7)
C1M0.50.5173 (3)0.250.0710 (10)
H1M10.56890.48380.25810.106*0.5
H1M20.43450.48380.14140.106*0.5
H1M30.49660.48380.35050.106*0.5
C20.59018 (15)0.7495 (2)0.2605 (3)0.0484 (6)
H20.65220.7020.26860.058*
C30.58925 (15)0.8928 (2)0.2590 (2)0.0469 (6)
C40.50.9686 (3)0.250.0461 (7)
N10.68412 (18)0.9648 (2)0.2580 (3)0.0644 (6)
O10.77696 (16)0.9086 (2)0.3351 (3)0.1026 (9)
O20.66271 (15)1.07438 (18)0.1755 (3)0.0839 (7)
N20.51.1226 (3)0.250.0628 (7)
O30.42778 (17)1.17968 (16)0.1136 (2)0.0843 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0550 (16)0.0382 (15)0.0610 (17)00.0354 (14)0
C1M0.080 (2)0.0383 (18)0.110 (3)00.061 (2)0
C20.0488 (11)0.0461 (13)0.0590 (12)0.0039 (8)0.0341 (9)0.0015 (8)
C30.0510 (11)0.0442 (12)0.0501 (12)0.0076 (8)0.0295 (9)0.0004 (8)
C40.0634 (17)0.0316 (14)0.0447 (15)00.0291 (13)0
N10.0655 (12)0.0616 (13)0.0735 (13)0.0185 (9)0.0413 (10)0.0014 (9)
O10.0558 (11)0.1121 (19)0.1362 (19)0.0093 (10)0.0473 (12)0.0236 (13)
O20.0995 (14)0.0671 (12)0.0990 (14)0.0237 (9)0.0613 (11)0.0091 (9)
N20.095 (2)0.0379 (14)0.0605 (17)00.0436 (16)0
O30.1239 (15)0.0468 (10)0.0731 (12)0.0180 (9)0.0446 (11)0.0156 (8)
Geometric parameters (Å, º) top
C1—C21.387 (2)C4—C3i1.383 (2)
C1—C2i1.387 (2)C4—N21.471 (4)
C1—C1M1.497 (4)N1—O11.208 (3)
C2—C31.369 (3)N1—O21.218 (2)
C3—C41.383 (2)N2—O3i1.213 (2)
C3—N11.470 (3)N2—O31.213 (2)
C2—C1—C2i117.5 (2)C3i—C4—N2121.55 (12)
C2—C1—C1M121.27 (12)C3—C4—N2121.55 (12)
C2i—C1—C1M121.27 (12)O1—N1—O2124.86 (18)
C3—C2—C1121.00 (17)O1—N1—C3117.4 (2)
C2—C3—C4121.82 (17)O2—N1—C3117.72 (19)
C2—C3—N1117.67 (17)O3i—N2—O3126.6 (3)
C4—C3—N1120.44 (19)O3i—N2—C4116.69 (14)
C3i—C4—C3116.9 (2)O3—N2—C4116.69 (14)
Symmetry code: (i) x+1, y, z+1/2.
(K20) top
Crystal data top
C7H5N3O6Z = 2
Mr = 227.14F(000) = 232
Triclinic, P1Dx = 1.635 Mg m3
a = 7.700 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.329 (2) ÅCell parameters from 855 reflections
c = 8.694 (2) Åθ = 2–22°
α = 87.89 (1)°µ = 0.15 mm1
β = 65.10 (1)°T = 293 K
γ = 67.33 (1)°Column, light yellow
V = 461.40 (19) Å30.4 × 0.2 × 0.2 mm
Data collection top
SMART
diffractometer
1165 independent reflections
Graphite monochromatorRint = 0.024
ω–scanθmax = 23°, θmin = 2°
Absorption correction: SADABS
?
h = 88
Tmin = 0.94, Tmax = 1k = 88
3177 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.059P)2 + 0.1766P]
where P = (Fo2 + 2Fc2)/3
1165 reflections(Δ/σ)max = 0.017
145 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C7H5N3O6γ = 67.33 (1)°
Mr = 227.14V = 461.40 (19) Å3
Triclinic, P1Z = 2
a = 7.700 (2) ÅMo Kα radiation
b = 8.329 (2) ŵ = 0.15 mm1
c = 8.694 (2) ÅT = 293 K
α = 87.89 (1)°0.4 × 0.2 × 0.2 mm
β = 65.10 (1)°
Data collection top
SMART
diffractometer
1165 independent reflections
Absorption correction: SADABS
?
Rint = 0.024
Tmin = 0.94, Tmax = 1θmax = 23°
3177 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.24 e Å3
1165 reflectionsΔρmin = 0.21 e Å3
145 parameters
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
C10.5306 (3)0.2715 (3)0.7162 (3)0.0475 (6)
C20.4326 (3)0.2750 (3)0.6125 (3)0.0427 (5)
C30.5364 (3)0.2471 (3)0.4362 (3)0.0438 (6)
C40.7444 (3)0.2201 (3)0.3578 (3)0.0512 (6)
C50.8458 (4)0.2176 (3)0.4567 (4)0.0611 (7)
H50.98640.19910.40430.073*
C60.7398 (4)0.2422 (3)0.6318 (3)0.0574 (7)
H60.81130.2390.69620.069*
C1M0.4228 (4)0.2909 (4)0.9079 (3)0.0677 (7)
H1110.2790.31050.94460.102*
H1120.42860.38910.95680.102*
H1130.49160.18550.94520.102*
N10.2113 (3)0.3027 (3)0.6933 (3)0.0550 (6)
O10.0856 (3)0.4387 (3)0.7903 (3)0.0828 (6)
O20.1696 (3)0.1866 (3)0.6560 (3)0.0741 (6)
N20.4223 (3)0.2403 (3)0.3377 (3)0.0544 (5)
O30.2715 (3)0.3729 (3)0.3544 (3)0.0783 (6)
O40.4827 (3)0.1017 (3)0.2528 (3)0.0764 (6)
N30.8586 (4)0.2005 (3)0.1702 (3)0.0715 (7)
O50.7567 (4)0.2705 (3)0.0919 (3)0.0918 (7)
O61.0476 (4)0.1175 (3)0.1069 (3)0.1043 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0502 (14)0.0483 (13)0.0545 (14)0.0224 (10)0.0303 (11)0.0092 (10)
C20.0368 (12)0.0449 (12)0.0512 (13)0.0187 (10)0.0221 (10)0.0093 (10)
C30.0478 (13)0.0412 (12)0.0519 (14)0.0211 (10)0.0279 (11)0.0095 (10)
C40.0485 (14)0.0519 (14)0.0520 (14)0.0257 (11)0.0162 (11)0.0052 (11)
C50.0399 (13)0.0653 (16)0.0814 (19)0.0271 (12)0.0244 (13)0.0079 (13)
C60.0536 (15)0.0654 (15)0.0707 (18)0.0286 (12)0.0391 (14)0.0111 (13)
C1M0.0759 (18)0.0845 (19)0.0556 (15)0.0357 (15)0.0379 (14)0.0130 (13)
N10.0433 (12)0.0693 (14)0.0577 (13)0.0248 (11)0.0258 (10)0.0143 (11)
O10.0472 (11)0.0913 (15)0.0806 (14)0.0121 (10)0.0152 (10)0.0084 (12)
O20.0598 (11)0.0904 (14)0.0970 (15)0.0468 (10)0.0426 (10)0.0226 (11)
N20.0663 (14)0.0574 (13)0.0568 (12)0.0315 (11)0.0374 (11)0.0170 (10)
O30.0816 (13)0.0755 (13)0.0938 (15)0.0213 (11)0.0629 (12)0.0189 (10)
O40.1145 (16)0.0657 (12)0.0776 (13)0.0439 (11)0.0610 (12)0.0097 (10)
N30.0675 (17)0.0764 (16)0.0629 (15)0.0406 (13)0.0113 (13)0.0020 (12)
O50.1097 (18)0.1111 (18)0.0592 (12)0.0575 (14)0.0310 (12)0.0256 (12)
O60.0641 (15)0.125 (2)0.0867 (16)0.0411 (13)0.0042 (12)0.0138 (14)
Geometric parameters (Å, º) top
C1—C61.381 (3)C4—N31.470 (3)
C1—C21.392 (3)C5—C61.369 (4)
C1—C1M1.498 (3)N1—O11.212 (3)
C2—C31.376 (3)N1—O21.221 (3)
C2—N11.467 (3)N2—O41.206 (3)
C3—C41.377 (3)N2—O31.213 (3)
C3—N21.478 (3)N3—O61.215 (3)
C4—C51.378 (3)N3—O51.219 (3)
C6—C1—C2116.0 (2)C6—C5—C4120.1 (2)
C6—C1—C1M120.6 (2)C5—C6—C1122.4 (2)
C2—C1—C1M123.3 (2)O1—N1—O2125.6 (2)
C3—C2—C1122.86 (19)O1—N1—C2117.4 (2)
C3—C2—N1118.08 (18)O2—N1—C2117.0 (2)
C1—C2—N1119.0 (2)O4—N2—O3125.8 (2)
C2—C3—C4119.01 (19)O4—N2—C3117.14 (19)
C2—C3—N2118.64 (19)O3—N2—C3117.0 (2)
C4—C3—N2122.3 (2)O6—N3—O5125.6 (3)
C3—C4—C5119.6 (2)O6—N3—C4116.9 (3)
C3—C4—N3121.1 (2)O5—N3—C4117.5 (2)
C5—C4—N3119.3 (2)
(K6) top
Crystal data top
C9H9N3O5F(000) = 496
Mr = 239.19Dx = 1.463 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.686 (2) ÅCell parameters from 1024 reflections
b = 11.368 (2) Åθ = 2–25°
c = 9.976 (2) ŵ = 0.12 mm1
β = 98.74 (2)°T = 293 K
V = 1085.7 (4) Å3Column, bright yellow
Z = 40.4 × 0.26 × 0.26 mm
Data collection top
SMART
diffractometer
1917 independent reflections
Graphite monochromatorRint = 0.027
ω–scanθmax = 25°, θmin = 2°
Absorption correction: SADABS
?
h = 1111
Tmin = 0.79, Tmax = 1k = 1313
8680 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.092P)2 + 0.5057P]
where P = (Fo2 + 2Fc2)/3
1917 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C9H9N3O5V = 1085.7 (4) Å3
Mr = 239.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.686 (2) ŵ = 0.12 mm1
b = 11.368 (2) ÅT = 293 K
c = 9.976 (2) Å0.4 × 0.26 × 0.26 mm
β = 98.74 (2)°
Data collection top
SMART
diffractometer
8680 measured reflections
Absorption correction: SADABS
?
1917 independent reflections
Tmin = 0.79, Tmax = 1Rint = 0.027
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.30 e Å3
1917 reflectionsΔρmin = 0.27 e Å3
154 parameters
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
C10.7689 (2)0.12669 (19)0.0674 (2)0.0467 (5)
C20.7933 (2)0.00603 (19)0.06609 (19)0.0418 (5)
C30.7191 (2)0.07198 (19)0.02665 (19)0.0416 (5)
C40.6158 (2)0.0250 (2)0.1244 (2)0.0511 (6)
H40.56540.07450.18810.061*
C50.5877 (2)0.0930 (2)0.1278 (2)0.0527 (6)
H50.51950.1240.19420.063*
C60.6614 (2)0.16557 (19)0.0318 (2)0.0484 (5)
C1M0.8600 (3)0.2112 (2)0.1574 (3)0.0689 (7)
H1M10.82430.28960.14220.103*
H1M20.95360.20770.13690.103*
H1M30.86020.19010.25070.103*
N1N0.91218 (19)0.04037 (18)0.16319 (19)0.0528 (5)
O11N0.9153 (2)0.0159 (2)0.28279 (18)0.0773 (6)
O12N0.99971 (17)0.09790 (18)0.1172 (2)0.0695 (6)
N2N0.6201 (2)0.29050 (19)0.0361 (2)0.0636 (6)
O21N0.6114 (3)0.3423 (2)0.1422 (2)0.0975 (8)
O22N0.5892 (3)0.3343 (2)0.0650 (3)0.1137 (10)
N1A0.7439 (2)0.19381 (16)0.02853 (17)0.0494 (5)
H1A0.75640.22470.10450.059*
C1A0.7499 (2)0.26651 (19)0.0804 (2)0.0484 (5)
O1A0.73809 (18)0.22804 (14)0.19282 (15)0.0570 (5)
C2A0.7702 (3)0.3941 (2)0.0523 (3)0.0703 (7)
H2A10.77720.40450.04190.106*
H2A20.69210.43830.07420.106*
H2A30.85440.42150.10670.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0435 (11)0.0536 (13)0.0432 (11)0.0071 (9)0.0072 (9)0.0016 (9)
C20.0370 (10)0.0525 (12)0.0348 (10)0.0014 (8)0.0023 (8)0.0045 (8)
C30.0434 (10)0.0505 (12)0.0314 (10)0.0027 (8)0.0069 (8)0.0005 (8)
C40.0518 (12)0.0625 (14)0.0363 (11)0.0045 (10)0.0024 (9)0.0015 (9)
C50.0481 (12)0.0650 (14)0.0426 (12)0.0043 (10)0.0010 (9)0.0093 (10)
C60.0473 (11)0.0506 (12)0.0483 (12)0.0031 (9)0.0103 (9)0.0060 (9)
C1M0.0700 (16)0.0615 (15)0.0714 (17)0.0159 (12)0.0011 (13)0.0103 (12)
N1N0.0440 (10)0.0649 (12)0.0462 (11)0.0072 (9)0.0033 (8)0.0109 (9)
O11N0.0779 (13)0.1006 (15)0.0452 (10)0.0102 (10)0.0167 (8)0.0018 (9)
O12N0.0478 (9)0.0823 (13)0.0785 (12)0.0145 (9)0.0096 (9)0.0246 (10)
N2N0.0668 (13)0.0568 (12)0.0670 (14)0.0056 (10)0.0096 (10)0.0079 (10)
O21N0.1194 (19)0.0785 (14)0.0916 (16)0.0231 (13)0.0066 (14)0.0291 (12)
O22N0.170 (3)0.0785 (15)0.1025 (18)0.0360 (16)0.0511 (18)0.0035 (13)
N1A0.0630 (11)0.0499 (11)0.0359 (9)0.0015 (8)0.0089 (8)0.0030 (7)
C1A0.0492 (12)0.0506 (12)0.0452 (12)0.0001 (9)0.0061 (9)0.0026 (9)
O1A0.0762 (11)0.0573 (10)0.0385 (8)0.0001 (8)0.0120 (7)0.0052 (7)
C2A0.0875 (19)0.0526 (15)0.0708 (17)0.0067 (13)0.0116 (14)0.0007 (12)
Geometric parameters (Å, º) top
C1—C21.392 (3)C6—N2N1.474 (3)
C1—C61.395 (3)N1N—O12N1.215 (3)
C1—C1M1.506 (3)N1N—O11N1.221 (3)
C2—C31.399 (3)N2N—O22N1.202 (3)
C2—N1N1.484 (3)N2N—O21N1.204 (3)
C3—C41.392 (3)N1A—C1A1.360 (3)
C3—N1A1.406 (3)C1A—O1A1.225 (3)
C4—C51.369 (3)C1A—C2A1.496 (3)
C5—C61.378 (3)
C2—C1—C6114.52 (18)C5—C6—N2N116.6 (2)
C2—C1—C1M123.3 (2)C1—C6—N2N119.7 (2)
C6—C1—C1M121.8 (2)O12N—N1N—O11N125.2 (2)
C1—C2—C3124.02 (18)O12N—N1N—C2117.48 (18)
C1—C2—N1N117.40 (18)O11N—N1N—C2117.3 (2)
C3—C2—N1N118.43 (19)O22N—N2N—O21N122.8 (2)
C4—C3—C2117.5 (2)O22N—N2N—C6118.4 (2)
C4—C3—N1A118.32 (18)O21N—N2N—C6118.6 (2)
C2—C3—N1A124.13 (18)C1A—N1A—C3125.05 (17)
C5—C4—C3120.8 (2)O1A—C1A—N1A121.1 (2)
C4—C5—C6119.3 (2)O1A—C1A—C2A123.4 (2)
C5—C6—C1123.8 (2)N1A—C1A—C2A115.5 (2)
(K12) top
Crystal data top
C9H10N2O3F(000) = 408
Mr = 194.19Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.430 (2) ÅCell parameters from 912 reflections
b = 9.991 (2) Åθ = 2–23°
c = 9.574 (2) ŵ = 0.1 mm1
β = 99.51 (1)°T = 293 K
V = 984.0 (3) Å3Needle, light yellow
Z = 40.4 × 0.12 × 0.12 mm
Data collection top
SMART
diffractometer
1735 independent reflections
Graphite monochromatorRint = 0.039
ω–scanθmax = 25°, θmin = 2°
Absorption correction: SADABS
?
h = 1212
Tmin = 0.92, Tmax = 1k = 1111
8196 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0705P)2 + 0.4277P]
where P = (Fo2 + 2Fc2)/3
1735 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C9H10N2O3V = 984.0 (3) Å3
Mr = 194.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.430 (2) ŵ = 0.1 mm1
b = 9.991 (2) ÅT = 293 K
c = 9.574 (2) Å0.4 × 0.12 × 0.12 mm
β = 99.51 (1)°
Data collection top
SMART
diffractometer
8196 measured reflections
Absorption correction: SADABS
?
1735 independent reflections
Tmin = 0.92, Tmax = 1Rint = 0.039
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å3
1735 reflectionsΔρmin = 0.21 e Å3
127 parameters
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
N1N0.7859 (2)0.0103 (2)0.7697 (2)0.0613 (6)
O1N0.8043 (2)0.0202 (2)0.8991 (2)0.0813 (7)
O2N0.6959 (2)0.0632 (2)0.6920 (2)0.0878 (8)
N1A0.7129 (2)0.1885 (2)0.54083 (19)0.0546 (6)
H1A0.68610.18550.4510.066*
C1A0.6281 (3)0.2297 (3)0.6237 (2)0.0533 (7)
O1A0.65474 (19)0.2237 (2)0.75322 (16)0.0677 (6)
C2A0.5021 (3)0.2819 (4)0.5476 (3)0.0809 (10)
H2A10.50150.27740.44730.121*
H2A20.49140.37310.57470.121*
H2A30.43220.22870.57150.121*
C1M1.2487 (3)0.0695 (4)0.7495 (4)0.0833 (10)
H1M11.30160.11540.69170.125*
H1M21.26570.02490.74770.125*
H1M31.26910.10160.84520.125*
C10.8807 (2)0.0646 (2)0.7041 (2)0.0470 (6)
C20.8422 (3)0.1500 (2)0.5905 (2)0.0471 (6)
C30.9415 (3)0.2032 (3)0.5261 (3)0.0573 (7)
H30.92020.25930.44820.069*
C41.0694 (3)0.1750 (3)0.5749 (3)0.0605 (7)
H41.13260.21030.52750.073*
C51.1075 (3)0.0952 (3)0.6933 (3)0.0566 (7)
C61.0103 (3)0.0406 (3)0.7566 (3)0.0545 (7)
H61.03220.01330.83620.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1N0.0792 (17)0.0519 (14)0.0531 (14)0.0075 (12)0.0115 (12)0.0074 (11)
O1N0.1033 (17)0.0910 (16)0.0517 (12)0.0046 (13)0.0192 (11)0.0255 (11)
O2N0.0965 (17)0.0813 (16)0.0834 (15)0.0362 (13)0.0087 (13)0.0008 (12)
N1A0.0639 (14)0.0724 (15)0.0260 (9)0.0041 (11)0.0028 (9)0.0005 (9)
C1A0.0620 (17)0.0624 (17)0.0351 (12)0.0010 (13)0.0073 (12)0.0040 (11)
O1A0.0810 (14)0.0915 (15)0.0305 (9)0.0082 (11)0.0086 (9)0.0069 (9)
C2A0.066 (2)0.117 (3)0.0570 (17)0.0120 (19)0.0039 (15)0.0038 (18)
C1M0.069 (2)0.085 (2)0.094 (2)0.0088 (17)0.0064 (18)0.0072 (19)
C10.0657 (17)0.0398 (13)0.0352 (12)0.0032 (12)0.0073 (11)0.0024 (10)
C20.0640 (17)0.0477 (14)0.0292 (11)0.0005 (12)0.0068 (11)0.0029 (10)
C30.075 (2)0.0554 (17)0.0434 (13)0.0042 (14)0.0147 (13)0.0083 (12)
C40.0687 (19)0.0565 (17)0.0606 (16)0.0048 (14)0.0232 (14)0.0017 (13)
C50.0667 (18)0.0489 (16)0.0537 (15)0.0022 (13)0.0083 (13)0.0087 (13)
C60.0731 (19)0.0447 (14)0.0439 (13)0.0056 (13)0.0040 (13)0.0030 (11)
Geometric parameters (Å, º) top
N1N—O2N1.217 (3)C1M—C51.505 (4)
N1N—O1N1.225 (3)C1—C61.383 (4)
N1N—C11.462 (3)C1—C21.389 (3)
N1A—C1A1.347 (3)C2—C31.395 (4)
N1A—C21.407 (3)C3—C41.368 (4)
C1A—O1A1.226 (3)C4—C51.389 (4)
C1A—C2A1.488 (4)C5—C61.377 (4)
O2N—N1N—O1N124.0 (2)C1—C2—C3116.1 (2)
O2N—N1N—C1117.9 (2)C1—C2—N1A124.7 (2)
O1N—N1N—C1118.1 (2)C3—C2—N1A119.1 (2)
C1A—N1A—C2124.77 (19)C4—C3—C2121.6 (2)
O1A—C1A—N1A121.3 (2)C3—C4—C5121.9 (3)
O1A—C1A—C2A123.1 (3)C6—C5—C4117.0 (3)
N1A—C1A—C2A115.5 (2)C6—C5—C1M121.6 (3)
C6—C1—C2122.0 (2)C4—C5—C1M121.4 (3)
C6—C1—N1N116.4 (2)C5—C6—C1121.2 (2)
C2—C1—N1N121.5 (2)
(K14) top
Crystal data top
C14H14N6O8Dx = 1.489 Mg m3
Mr = 394.31Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmc21Cell parameters from 790 reflections
a = 12.239 (2) Åθ = 2–24°
b = 10.582 (2) ŵ = 0.12 mm1
c = 13.582 (3) ÅT = 293 K
V = 1759.0 (6) Å3Orange, needle
Z = 40.32 × 0.14 × 0.12 mm
F(000) = 816
Data collection top
SMART
diffractometer
1416 independent reflections
Graphite monochromatorRint = 0.026
ω–scanθmax = 25°, θmin = 2°
Absorption correction: SADABS
?
h = 1414
Tmin = 0.89, Tmax = 1k = 128
4779 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0757P)2 + 0.3587P]
where P = (Fo2 + 2Fc2)/3
765 reflections(Δ/σ)max = 0.717
140 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C14H14N6O8V = 1759.0 (6) Å3
Mr = 394.31Z = 4
Orthorhombic, Cmc21Mo Kα radiation
a = 12.239 (2) ŵ = 0.12 mm1
b = 10.582 (2) ÅT = 293 K
c = 13.582 (3) Å0.32 × 0.14 × 0.12 mm
Data collection top
SMART
diffractometer
4779 measured reflections
Absorption correction: SADABS
?
1416 independent reflections
Tmin = 0.89, Tmax = 1Rint = 0.026
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.15(Δ/σ)max = 0.717
765 reflectionsΔρmax = 0.19 e Å3
140 parametersΔρmin = 0.17 e Å3
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*/UeqOcc. (<1)
C1A0.50.9173 (4)0.1429 (4)0.0578 (12)
C2A0.4055 (2)0.9918 (4)0.1400 (3)0.0540 (7)
C3A0.4034 (3)1.1216 (3)0.1352 (3)0.0559 (8)
H3A0.33681.16390.13420.067*
C4A0.51.1897 (5)0.1318 (4)0.0549 (11)
C5A0.50.7766 (5)0.1590 (5)0.0820 (19)
H5A10.42620.74580.15790.123*0.5
H5A20.53240.75780.22170.123*0.5
H5A30.54130.73630.10780.123*0.5
N1A0.51.3184 (4)0.1245 (4)0.0774 (15)
H1A10.43911.35890.1220.093*0.5
H1A20.56091.3590.12250.093*0.5
N2A0.2969 (3)0.9313 (3)0.1404 (3)0.0710 (9)
O1A0.2840 (3)0.8365 (3)0.0926 (4)0.0964 (11)
O2A0.2243 (2)0.9814 (3)0.1878 (4)0.0997 (11)
C1B0.51.3390 (4)0.3885 (4)0.0559 (11)
C2B0.5945 (2)1.2647 (3)0.3879 (3)0.0548 (8)
C3B0.5969 (2)1.1352 (3)0.3861 (3)0.0541 (8)
H3B0.66361.09320.38460.065*
C4B0.51.0662 (4)0.3867 (4)0.0480 (10)
C5B0.51.4824 (5)0.3776 (6)0.0803 (17)
H5B10.57381.5130.37980.12*0.5
H5B20.45881.51940.43040.12*0.5
H5B30.46741.5050.31580.12*0.5
N1B0.50.9370 (4)0.3858 (4)0.0631 (10)
H1B10.56080.89640.38490.076*0.5
H1B20.43920.89640.38620.076*0.5
N2B0.7023 (3)1.3252 (3)0.3949 (3)0.0767 (9)
O1B0.7108 (3)1.4184 (3)0.4477 (4)0.1015 (11)
O2B0.7784 (3)1.2782 (3)0.3501 (5)0.1116 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.070 (3)0.059 (3)0.045 (2)000.002 (2)
C2A0.0463 (15)0.0628 (16)0.0527 (15)0.0061 (15)0.0049 (17)0.0017 (16)
C3A0.0468 (18)0.0641 (18)0.0569 (17)0.0024 (13)0.0021 (16)0.0016 (16)
C4A0.048 (2)0.058 (3)0.058 (3)000.004 (2)
C5A0.119 (5)0.051 (3)0.076 (4)000.002 (3)
N1A0.060 (2)0.055 (2)0.116 (5)000.011 (3)
N2A0.0599 (18)0.0795 (19)0.0737 (19)0.0190 (16)0.0087 (17)0.0021 (17)
O1A0.091 (2)0.095 (2)0.103 (2)0.0444 (18)0.014 (2)0.0178 (19)
O2A0.0592 (15)0.113 (2)0.127 (3)0.0136 (17)0.026 (2)0.007 (2)
C1B0.057 (3)0.057 (2)0.053 (2)000.001 (2)
C2B0.0469 (17)0.0623 (16)0.0552 (17)0.0094 (13)0.0022 (16)0.0015 (18)
C3B0.0408 (17)0.0660 (18)0.0554 (16)0.0054 (13)0.0002 (15)0.0009 (16)
C4B0.045 (2)0.053 (2)0.046 (2)000.002 (2)
C5B0.091 (3)0.054 (3)0.096 (5)000.004 (3)
N1B0.055 (2)0.058 (2)0.077 (3)000.003 (2)
N2B0.060 (2)0.082 (2)0.088 (2)0.0209 (16)0.0092 (18)0.0150 (19)
O1B0.095 (2)0.0926 (18)0.117 (3)0.0395 (19)0.023 (2)0.001 (2)
O2B0.0542 (17)0.124 (3)0.157 (4)0.0172 (15)0.024 (2)0.005 (3)
Geometric parameters (Å, º) top
C1A—C2Ai1.400 (4)C1B—C2Bi1.399 (4)
C1A—C2A1.400 (4)C1B—C2B1.399 (4)
C1A—C5A1.505 (6)C1B—C5B1.524 (5)
C2A—C3A1.375 (5)C2B—C3B1.371 (4)
C2A—N2A1.476 (4)C2B—N2B1.469 (4)
C3A—C4A1.385 (4)C3B—C4B1.393 (4)
C4A—N1A1.366 (6)C4B—N1B1.367 (5)
C4A—C3Ai1.385 (4)C4B—C3Bi1.393 (4)
N2A—O1A1.205 (5)N2B—O2B1.219 (5)
N2A—O2A1.219 (5)N2B—O1B1.224 (5)
C2Ai—C1A—C2A111.3 (4)C2Bi—C1B—C2B111.6 (4)
C2Ai—C1A—C5A124.2 (2)C2Bi—C1B—C5B123.99 (19)
C2A—C1A—C5A124.2 (2)C2B—C1B—C5B123.99 (19)
C3A—C2A—C1A125.4 (3)C3B—C2B—C1B125.4 (3)
C3A—C2A—N2A114.6 (3)C3B—C2B—N2B114.7 (3)
C1A—C2A—N2A119.9 (3)C1B—C2B—N2B119.8 (3)
C2A—C3A—C4A120.3 (3)C2B—C3B—C4B120.4 (3)
N1A—C4A—C3A121.4 (2)N1B—C4B—C3B121.63 (19)
N1A—C4A—C3Ai121.4 (2)N1B—C4B—C3Bi121.63 (19)
C3A—C4A—C3Ai117.2 (4)C3B—C4B—C3Bi116.7 (4)
O1A—N2A—O2A123.5 (3)O2B—N2B—O1B123.8 (3)
O1A—N2A—C2A118.5 (3)O2B—N2B—C2B118.4 (4)
O2A—N2A—C2A118.0 (3)O1B—N2B—C2B117.8 (4)
Symmetry code: (i) x+1, y, z.

Experimental details

(K15)(K19)(K20)(K6)
Crystal data
Chemical formulaC8H6BrIN2O3C7H5N3O6C7H5N3O6C9H9N3O5
Mr384.96227.14227.14239.19
Crystal system, space groupTriclinic, P1Monoclinic, C2/cTriclinic, P1Monoclinic, P21/c
Temperature (K)293293293293
a, b, c (Å)4.797 (2), 7.673 (2), 15.654 (4)13.644 (1), 9.550 (1), 8.754 (1)7.700 (2), 8.329 (2), 8.694 (2)9.686 (2), 11.368 (2), 9.976 (2)
α, β, γ (°)96.98 (2), 97.03 (2), 103.34 (2)90, 121.31 (2), 9087.89 (1), 65.10 (1), 67.33 (1)90, 98.74 (2), 90
V3)549.7 (3)974.53 (17)461.40 (19)1085.7 (4)
Z2424
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)6.540.140.150.12
Crystal size (mm)0.3 × 0.25 × 0.150.36 × 0.3 × 0.260.4 × 0.2 × 0.20.4 × 0.26 × 0.26
Data collection
DiffractometerSMART
diffractometer
SMART
diffractometer
SMART
diffractometer
SMART
diffractometer
Absorption correctionSADABSSADABSSADABSSADABS
Tmin, Tmax0.62, 10.79, 10.94, 10.79, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
4680, 1947, ? 2636, 763, ? 3177, 1165, ? 8680, 1917, ?
Rint0.0340.0320.0240.027
θmax (°)25242325
(sin θ/λ)max1)0.5950.5720.5500.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.098, ? 0.034, 0.147, 0.81 0.037, 0.111, 1.06 0.051, 0.165, 1.06
No. of reflections194776311651917
No. of parameters13675145154
No. of restraints0000
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 refinementH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max0.0130.0040.0170.001
Δρmax, Δρmin (e Å3)0.59, 1.480.15, 0.150.24, 0.210.30, 0.27


(K12)(K14)
Crystal data
Chemical formulaC9H10N2O3C14H14N6O8
Mr194.19394.31
Crystal system, space groupMonoclinic, P21/cOrthorhombic, Cmc21
Temperature (K)293293
a, b, c (Å)10.430 (2), 9.991 (2), 9.574 (2)12.239 (2), 10.582 (2), 13.582 (3)
α, β, γ (°)90, 99.51 (1), 9090, 90, 90
V3)984.0 (3)1759.0 (6)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.10.12
Crystal size (mm)0.4 × 0.12 × 0.120.32 × 0.14 × 0.12
Data collection
DiffractometerSMART
diffractometer
SMART
diffractometer
Absorption correctionSADABSSADABS
Tmin, Tmax0.92, 10.89, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
8196, 1735, ? 4779, 1416, ?
Rint0.0390.026
θmax (°)2525
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.157, 1.05 0.037, 0.119, 1.15
No. of reflections1735765
No. of parameters127140
No. of restraints01
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max< 0.0010.717
Δρmax, Δρmin (e Å3)0.23, 0.210.19, 0.17

Computer programs: SIR2000 (Burla et al., 2001), SHELXL97 (Sheldrick, 1997), SCHAKAL (Keller, 1993).

 

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