Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614018952/eb5032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614018952/eb5032tpr375sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614018952/eb5032emku145sup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614018952/eb5032sup4.pdf |
CCDC references: 1020675; 1020676
Crystal data, data collection and structure refinement details are summarized in Table 1.
Data collection: Bruker SMART for tpr375; CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for emku145. Cell refinement: Bruker SMART for tpr375; CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for emku145. Data reduction: Bruker SAINT for tpr375; CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for emku145. For both compounds, program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008).
C12H14N2O10 | Z = 2 |
Mr = 346.25 | F(000) = 360 |
Triclinic, P1 | Dx = 1.611 Mg m−3 |
a = 8.1895 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8902 (9) Å | Cell parameters from 5586 reflections |
c = 10.6709 (9) Å | θ = 0.00–0.00° |
α = 113.376 (1)° | µ = 0.14 mm−1 |
β = 104.250 (1)° | T = 273 K |
γ = 103.472 (1)° | 0.42 × 0.40 × 0.26 mm |
V = 713.87 (11) Å3 |
CCD area detector diffractometer | 2770 independent reflections |
Radiation source: fine-focus sealed tube | 2485 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
phi and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan SADABS | h = −10→10 |
Tmin = 0.942, Tmax = 0.964 | k = −12→12 |
7343 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0624P)2 + 0.111P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2770 reflections | Δρmax = 0.19 e Å−3 |
236 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (4) |
C12H14N2O10 | γ = 103.472 (1)° |
Mr = 346.25 | V = 713.87 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1895 (7) Å | Mo Kα radiation |
b = 9.8902 (9) Å | µ = 0.14 mm−1 |
c = 10.6709 (9) Å | T = 273 K |
α = 113.376 (1)° | 0.42 × 0.40 × 0.26 mm |
β = 104.250 (1)° |
CCD area detector diffractometer | 2770 independent reflections |
Absorption correction: multi-scan SADABS | 2485 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.964 | Rint = 0.023 |
7343 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.19 e Å−3 |
2770 reflections | Δρmin = −0.22 e Å−3 |
236 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.30523 (16) | 0.38307 (15) | 0.27100 (14) | 0.0359 (3) | |
C2 | 0.38612 (16) | 0.54886 (15) | 0.30038 (14) | 0.0369 (3) | |
H2A | 0.3018 | 0.5906 | 0.2725 | 0.044* | |
C3 | 0.55791 (17) | 0.64788 (15) | 0.35951 (14) | 0.0365 (3) | |
H3 | 0.5756 | 0.7478 | 0.3677 | 0.044* | |
C4 | 0.72464 (16) | 0.62028 (14) | 0.41404 (13) | 0.0337 (3) | |
C5 | 1.05012 (16) | 0.72501 (15) | 0.52427 (16) | 0.0404 (3) | |
H5A | 1.0584 | 0.6343 | 0.4487 | 0.048* | |
H5B | 1.0553 | 0.7071 | 0.6080 | 0.048* | |
C6 | 1.20698 (16) | 0.87195 (15) | 0.57111 (14) | 0.0353 (3) | |
C7 | −0.19123 (16) | 0.15212 (15) | 0.75852 (14) | 0.0371 (3) | |
C8 | −0.11311 (17) | 0.04642 (14) | 0.79785 (14) | 0.0379 (3) | |
H8 | −0.1988 | −0.0474 | 0.7779 | 0.046* | |
C9 | 0.05829 (17) | 0.06284 (15) | 0.85670 (14) | 0.0381 (3) | |
H9 | 0.0742 | −0.0204 | 0.8717 | 0.046* | |
C10 | 0.22671 (16) | 0.19506 (14) | 0.90154 (13) | 0.0348 (3) | |
C11 | 0.55194 (16) | 0.30275 (15) | 1.00200 (15) | 0.0387 (3) | |
H11A | 0.5565 | 0.4022 | 1.0757 | 0.046* | |
H11B | 0.5619 | 0.3158 | 0.9184 | 0.046* | |
C12 | 0.70842 (16) | 0.26459 (15) | 1.06553 (14) | 0.0368 (3) | |
H1X | 0.883 (2) | 0.823 (2) | 0.4682 (18) | 0.055 (5)* | |
H3X | 1.460 (3) | 0.953 (2) | 0.6475 (19) | 0.071 (5)* | |
H10X | 0.960 (3) | 0.350 (2) | 1.153 (2) | 0.077 (6)* | |
H2Y | 0.382 (2) | 0.100 (2) | 0.9632 (18) | 0.063 (5)* | |
N1 | 0.87948 (14) | 0.73978 (13) | 0.46740 (12) | 0.0367 (3) | |
N2 | 0.38042 (14) | 0.17905 (13) | 0.95489 (12) | 0.0376 (3) | |
O1 | 0.14090 (12) | 0.31373 (12) | 0.21363 (12) | 0.0521 (3) | |
O2 | 0.40728 (12) | 0.31060 (11) | 0.30544 (12) | 0.0478 (3) | |
H2X | 0.5142 | 0.3697 | 0.3421 | 0.072* | |
O3 | 0.72413 (12) | 0.49293 (11) | 0.41169 (12) | 0.0456 (3) | |
O4 | 1.19149 (12) | 0.98929 (11) | 0.56895 (11) | 0.0464 (3) | |
O5 | 1.36132 (12) | 0.85533 (12) | 0.61524 (13) | 0.0525 (3) | |
O6 | −0.35560 (12) | 0.11275 (12) | 0.70682 (12) | 0.0516 (3) | |
O7 | −0.08702 (12) | 0.28594 (11) | 0.77821 (13) | 0.0496 (3) | |
H7X | 0.0193 | 0.3011 | 0.8194 | 0.074* | |
O8 | 0.22971 (12) | 0.31704 (11) | 0.89144 (12) | 0.0481 (3) | |
O9 | 0.69398 (13) | 0.14374 (12) | 1.07034 (13) | 0.0554 (3) | |
O10 | 0.86250 (13) | 0.38047 (12) | 1.11300 (13) | 0.0561 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0241 (6) | 0.0358 (6) | 0.0467 (6) | 0.0086 (5) | 0.0074 (5) | 0.0237 (5) |
C2 | 0.0258 (6) | 0.0359 (6) | 0.0536 (7) | 0.0134 (5) | 0.0103 (5) | 0.0274 (6) |
C3 | 0.0295 (6) | 0.0300 (6) | 0.0526 (7) | 0.0113 (5) | 0.0115 (5) | 0.0246 (5) |
C4 | 0.0249 (6) | 0.0305 (6) | 0.0438 (6) | 0.0075 (5) | 0.0086 (5) | 0.0205 (5) |
C5 | 0.0231 (6) | 0.0364 (7) | 0.0628 (8) | 0.0084 (5) | 0.0086 (5) | 0.0309 (6) |
C6 | 0.0254 (6) | 0.0332 (6) | 0.0473 (7) | 0.0095 (5) | 0.0098 (5) | 0.0224 (5) |
C7 | 0.0251 (6) | 0.0335 (6) | 0.0506 (7) | 0.0093 (5) | 0.0097 (5) | 0.0220 (5) |
C8 | 0.0280 (6) | 0.0294 (6) | 0.0542 (7) | 0.0064 (5) | 0.0113 (5) | 0.0231 (5) |
C9 | 0.0309 (6) | 0.0316 (6) | 0.0544 (7) | 0.0117 (5) | 0.0115 (5) | 0.0258 (6) |
C10 | 0.0264 (6) | 0.0328 (6) | 0.0438 (6) | 0.0110 (5) | 0.0087 (5) | 0.0198 (5) |
C11 | 0.0257 (6) | 0.0349 (6) | 0.0555 (7) | 0.0102 (5) | 0.0091 (5) | 0.0260 (6) |
C12 | 0.0267 (6) | 0.0349 (6) | 0.0487 (7) | 0.0109 (5) | 0.0096 (5) | 0.0232 (5) |
N1 | 0.0236 (5) | 0.0308 (5) | 0.0556 (6) | 0.0075 (4) | 0.0086 (5) | 0.0260 (5) |
N2 | 0.0254 (6) | 0.0330 (6) | 0.0542 (6) | 0.0101 (4) | 0.0083 (5) | 0.0251 (5) |
O1 | 0.0233 (5) | 0.0473 (6) | 0.0793 (7) | 0.0063 (4) | 0.0042 (4) | 0.0374 (5) |
O2 | 0.0239 (4) | 0.0361 (5) | 0.0798 (7) | 0.0068 (4) | 0.0052 (4) | 0.0355 (5) |
O3 | 0.0245 (4) | 0.0337 (5) | 0.0772 (6) | 0.0086 (4) | 0.0079 (4) | 0.0334 (5) |
O4 | 0.0295 (5) | 0.0350 (5) | 0.0742 (6) | 0.0110 (4) | 0.0116 (4) | 0.0312 (5) |
O5 | 0.0225 (5) | 0.0434 (6) | 0.0914 (8) | 0.0105 (4) | 0.0096 (5) | 0.0402 (5) |
O6 | 0.0232 (5) | 0.0470 (5) | 0.0826 (7) | 0.0093 (4) | 0.0093 (4) | 0.0378 (5) |
O7 | 0.0243 (4) | 0.0391 (5) | 0.0850 (7) | 0.0088 (4) | 0.0072 (4) | 0.0391 (5) |
O8 | 0.0259 (4) | 0.0358 (5) | 0.0805 (7) | 0.0090 (4) | 0.0077 (4) | 0.0347 (5) |
O9 | 0.0310 (5) | 0.0437 (6) | 0.0929 (8) | 0.0116 (4) | 0.0093 (5) | 0.0437 (6) |
O10 | 0.0241 (5) | 0.0458 (6) | 0.0951 (8) | 0.0063 (4) | 0.0074 (5) | 0.0434 (6) |
C1—O1 | 1.2196 (15) | C8—C9 | 1.3304 (18) |
C1—O2 | 1.2977 (15) | C8—H8 | 0.9300 |
C1—C2 | 1.4864 (17) | C9—C10 | 1.4763 (17) |
C2—C3 | 1.3294 (17) | C9—H9 | 0.9300 |
C2—H2A | 0.9300 | C10—O8 | 1.2483 (15) |
C3—C4 | 1.4785 (17) | C10—N2 | 1.3211 (16) |
C3—H3 | 0.9300 | C11—N2 | 1.4444 (16) |
C4—O3 | 1.2488 (15) | C11—C12 | 1.4983 (17) |
C4—N1 | 1.3196 (16) | C11—H11A | 0.9700 |
C5—N1 | 1.4459 (16) | C11—H11B | 0.9700 |
C5—C6 | 1.4999 (17) | C12—O9 | 1.1963 (16) |
C5—H5A | 0.9700 | C12—O10 | 1.3089 (16) |
C5—H5B | 0.9700 | N1—H1X | 0.814 (19) |
C6—O4 | 1.2048 (15) | N2—H2Y | 0.83 (2) |
C6—O5 | 1.3083 (15) | O2—H2X | 0.8200 |
C7—O6 | 1.2197 (16) | O5—H3X | 0.97 (2) |
C7—O7 | 1.2996 (15) | O7—H7X | 0.8200 |
C7—C8 | 1.4851 (17) | O10—H10X | 0.98 (2) |
O1—C1—O2 | 119.35 (12) | C7—C8—H8 | 114.4 |
O1—C1—C2 | 119.79 (11) | C8—C9—C10 | 128.92 (11) |
O2—C1—C2 | 120.86 (11) | C8—C9—H9 | 115.5 |
C3—C2—C1 | 131.26 (11) | C10—C9—H9 | 115.5 |
C3—C2—H2A | 114.4 | O8—C10—N2 | 119.96 (12) |
C1—C2—H2A | 114.4 | O8—C10—C9 | 123.81 (11) |
C2—C3—C4 | 128.65 (11) | N2—C10—C9 | 116.23 (11) |
C2—C3—H3 | 115.7 | N2—C11—C12 | 111.43 (11) |
C4—C3—H3 | 115.7 | N2—C11—H11A | 109.3 |
O3—C4—N1 | 120.25 (11) | C12—C11—H11A | 109.3 |
O3—C4—C3 | 123.57 (11) | N2—C11—H11B | 109.3 |
N1—C4—C3 | 116.18 (11) | C12—C11—H11B | 109.3 |
N1—C5—C6 | 110.85 (11) | H11A—C11—H11B | 108.0 |
N1—C5—H5A | 109.5 | O9—C12—O10 | 124.84 (12) |
C6—C5—H5A | 109.5 | O9—C12—C11 | 124.43 (12) |
N1—C5—H5B | 109.5 | O10—C12—C11 | 110.72 (11) |
C6—C5—H5B | 109.5 | C4—N1—C5 | 120.44 (11) |
H5A—C5—H5B | 108.1 | C4—N1—H1X | 121.7 (12) |
O4—C6—O5 | 125.04 (11) | C5—N1—H1X | 117.9 (13) |
O4—C6—C5 | 124.12 (11) | C10—N2—C11 | 120.08 (11) |
O5—C6—C5 | 110.84 (11) | C10—N2—H2Y | 121.6 (13) |
O6—C7—O7 | 119.47 (12) | C11—N2—H2Y | 118.3 (13) |
O6—C7—C8 | 119.56 (11) | C1—O2—H2X | 109.5 |
O7—C7—C8 | 120.97 (11) | C6—O5—H3X | 108.7 (12) |
C9—C8—C7 | 131.11 (12) | C7—O7—H7X | 109.5 |
C9—C8—H8 | 114.4 | C12—O10—H10X | 107.6 (12) |
C5H6N2O4 | Dx = 1.597 Mg m−3 |
Mr = 158.12 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 1214 reflections |
a = 10.4325 (8) Å | θ = 3.3–28.6° |
b = 6.7755 (12) Å | µ = 0.14 mm−1 |
c = 18.6056 (14) Å | T = 293 K |
V = 1315.1 (3) Å3 | Block, colorless |
Z = 8 | 0.42 × 0.38 × 0.31 mm |
F(000) = 656 |
Xcalibur, Eos, Gemini diffractometer | 1345 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1124 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −12→13 |
Tmin = 0.944, Tmax = 0.958 | k = −4→8 |
3214 measured reflections | l = −23→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
1345 reflections | (Δ/σ)max = 0.001 |
109 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C5H6N2O4 | V = 1315.1 (3) Å3 |
Mr = 158.12 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 10.4325 (8) Å | µ = 0.14 mm−1 |
b = 6.7755 (12) Å | T = 293 K |
c = 18.6056 (14) Å | 0.42 × 0.38 × 0.31 mm |
Xcalibur, Eos, Gemini diffractometer | 1345 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 1124 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.958 | Rint = 0.024 |
3214 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.21 e Å−3 |
1345 reflections | Δρmin = −0.19 e Å−3 |
109 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
H2A | 0.138 (2) | 0.136 (3) | 0.2670 (12) | 0.047 (6)* | |
H2B | 0.146 (2) | 0.201 (3) | 0.1884 (14) | 0.058 (7)* | |
C1 | 0.60903 (17) | 0.4391 (3) | 0.10008 (9) | 0.0355 (5) | |
C2 | 0.55302 (17) | 0.3068 (3) | 0.04661 (9) | 0.0377 (5) | |
H2 | 0.6013 | 0.2796 | 0.0058 | 0.045* | |
C3 | 0.43954 (17) | 0.2232 (3) | 0.05173 (10) | 0.0363 (5) | |
H3 | 0.4168 | 0.1424 | 0.0134 | 0.044* | |
C4 | 0.34293 (16) | 0.2388 (2) | 0.10956 (9) | 0.0321 (4) | |
C5 | 0.30376 (16) | 0.1547 (3) | 0.23569 (9) | 0.0310 (4) | |
N1 | 0.38049 (14) | 0.1807 (2) | 0.17645 (7) | 0.0315 (4) | |
H1 | 0.4609 | 0.1578 | 0.1822 | 0.038* | |
N2 | 0.17948 (14) | 0.1686 (3) | 0.22836 (10) | 0.0396 (4) | |
O1 | 0.54714 (11) | 0.5343 (2) | 0.14280 (7) | 0.0439 (4) | |
O2 | 0.73458 (11) | 0.4433 (2) | 0.09632 (7) | 0.0476 (4) | |
H2C | 0.7631 | 0.5083 | 0.1299 | 0.071* | |
O3 | 0.23415 (11) | 0.2908 (2) | 0.09558 (7) | 0.0441 (4) | |
O4 | 0.35592 (11) | 0.1137 (2) | 0.29397 (6) | 0.0404 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0298 (8) | 0.0427 (10) | 0.0341 (9) | −0.0012 (8) | 0.0038 (7) | 0.0033 (8) |
C2 | 0.0363 (10) | 0.0496 (11) | 0.0274 (9) | 0.0030 (9) | 0.0030 (7) | −0.0024 (8) |
C3 | 0.0366 (10) | 0.0429 (10) | 0.0295 (9) | 0.0018 (8) | −0.0036 (7) | −0.0074 (8) |
C4 | 0.0305 (9) | 0.0339 (9) | 0.0319 (9) | −0.0022 (7) | −0.0050 (7) | −0.0036 (7) |
C5 | 0.0276 (8) | 0.0334 (9) | 0.0320 (9) | −0.0039 (7) | −0.0037 (7) | −0.0045 (7) |
N1 | 0.0222 (7) | 0.0404 (8) | 0.0320 (8) | −0.0014 (6) | −0.0025 (6) | −0.0018 (6) |
N2 | 0.0249 (8) | 0.0571 (11) | 0.0367 (9) | −0.0023 (7) | 0.0000 (7) | 0.0025 (8) |
O1 | 0.0320 (7) | 0.0521 (8) | 0.0476 (8) | −0.0003 (6) | 0.0047 (6) | −0.0122 (7) |
O2 | 0.0299 (7) | 0.0645 (10) | 0.0484 (8) | −0.0074 (6) | 0.0087 (5) | −0.0118 (7) |
O3 | 0.0304 (7) | 0.0626 (9) | 0.0393 (7) | 0.0075 (6) | −0.0062 (5) | 0.0027 (6) |
O4 | 0.0300 (7) | 0.0603 (9) | 0.0311 (7) | −0.0078 (6) | −0.0036 (5) | 0.0008 (6) |
C1—O1 | 1.210 (2) | C4—N1 | 1.363 (2) |
C1—O2 | 1.312 (2) | C5—O4 | 1.245 (2) |
C1—C2 | 1.461 (2) | C5—N2 | 1.307 (2) |
C2—C3 | 1.316 (2) | C5—N1 | 1.373 (2) |
C2—H2 | 0.9300 | N1—H1 | 0.8600 |
C3—C4 | 1.478 (2) | N2—H2A | 0.87 (2) |
C3—H3 | 0.9300 | N2—H2B | 0.85 (3) |
C4—O3 | 1.216 (2) | O2—H2C | 0.8200 |
O1—C1—O2 | 123.76 (17) | N1—C4—C3 | 116.61 (15) |
O1—C1—C2 | 124.12 (16) | O4—C5—N2 | 122.73 (17) |
O2—C1—C2 | 112.12 (15) | O4—C5—N1 | 118.22 (15) |
C3—C2—C1 | 125.07 (16) | N2—C5—N1 | 119.02 (16) |
C3—C2—H2 | 117.5 | C4—N1—C5 | 127.03 (15) |
C1—C2—H2 | 117.5 | C4—N1—H1 | 116.5 |
C2—C3—C4 | 129.44 (16) | C5—N1—H1 | 116.5 |
C2—C3—H3 | 115.3 | C5—N2—H2A | 112.9 (15) |
C4—C3—H3 | 115.3 | C5—N2—H2B | 121.2 (18) |
O3—C4—N1 | 123.17 (17) | H2A—N2—H2B | 126 (2) |
O3—C4—C3 | 120.09 (16) | C1—O2—H2C | 109.5 |
Experimental details
(tpr375) | (emku145) | |
Crystal data | ||
Chemical formula | C12H14N2O10 | C5H6N2O4 |
Mr | 346.25 | 158.12 |
Crystal system, space group | Triclinic, P1 | Orthorhombic, Pbcn |
Temperature (K) | 273 | 293 |
a, b, c (Å) | 8.1895 (7), 9.8902 (9), 10.6709 (9) | 10.4325 (8), 6.7755 (12), 18.6056 (14) |
α, β, γ (°) | 113.376 (1), 104.250 (1), 103.472 (1) | 90, 90, 90 |
V (Å3) | 713.87 (11) | 1315.1 (3) |
Z | 2 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.14 |
Crystal size (mm) | 0.42 × 0.40 × 0.26 | 0.42 × 0.38 × 0.31 |
Data collection | ||
Diffractometer | CCD area detector diffractometer | Xcalibur, Eos, Gemini diffractometer |
Absorption correction | Multi-scan SADABS | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.942, 0.964 | 0.944, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7343, 2770, 2485 | 3214, 1345, 1124 |
Rint | 0.023 | 0.024 |
(sin θ/λ)max (Å−1) | 0.617 | 0.625 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.103, 1.05 | 0.041, 0.140, 0.97 |
No. of reflections | 2770 | 1345 |
No. of parameters | 236 | 109 |
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 |
Δρmax, Δρmin (e Å−3) | 0.19, −0.22 | 0.21, −0.19 |
Computer programs: Bruker SMART, CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44), Bruker SAINT, SHELXL97 (Sheldrick, 2008).