Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620014936/px5028sup1.cif | |
Zip compressed file https://doi.org/10.1107/S2052520620014936/px5028sup2.zip | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014936/px50281Cusup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014936/px50282Cusup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014936/px50283Cusup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014936/px50283Mosup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014936/px50281Neusup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620014936/px5028sup8.pdf | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520620014936/px50281Cusup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520620014936/px50282Cusup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520620014936/px50283Cusup11.cml |
CCDC references: 2008294; 2008303; 2047732; 2008180; 2008224
Data collection: CrysAlis PRO (Agilent, 2014) for 1Cu, 2Cu, 3Cu, 3Mo; SXD2001 (Gutmann, 2005) for 1Neu. Cell refinement: CrysAlis PRO (Agilent, 2014) for 1Cu, 2Cu, 3Cu, 3Mo. Data reduction: CrysAlis PRO (Agilent, 2014) for 1Cu, 2Cu, 3Cu, 3Mo; SXD2001 (Gutmann, 2005) for 1Neu. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for 1Cu, 2Cu, 3Cu, 3Mo. Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for 1Cu, 2Cu, 3Cu, 3Mo; SHELXL97 (Sheldrick, 2008) for 1Neu. Molecular graphics: OLEX2 (Dolomanov et al., 2009) for 1Cu, 2Cu, 3Cu, 3Mo. Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for 1Cu, 2Cu, 3Cu, 3Mo.
C10H11NO3 | F(000) = 408 |
Mr = 193.20 | Dx = 1.413 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 8.6896 (1) Å | Cell parameters from 25673 reflections |
b = 10.8910 (1) Å | θ = 4.6–71.4° |
c = 9.5960 (1) Å | µ = 0.88 mm−1 |
β = 90.075 (1)° | T = 100 K |
V = 908.15 (2) Å3 | Block |
Z = 4 | 0.34 × 0.26 × 0.17 mm |
Agilent SuperNova Dual four-circle diffractometer with an Atlas detector | 1767 independent reflections |
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source | 1728 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 5.2195 pixels mm-1 | θmax = 71.5°, θmin = 5.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −13→13 |
Tmin = 0.700, Tmax = 1.000 | l = −11→11 |
31209 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0388P)2 + 0.509P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1767 reflections | Δρmax = 0.27 e Å−3 |
128 parameters | Δρmin = −0.28 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.36276 (10) | 0.47007 (8) | 0.14418 (9) | 0.0164 (2) | |
O3 | 0.16094 (9) | 0.19482 (7) | −0.03330 (8) | 0.0137 (2) | |
O2 | 0.57726 (10) | 0.16063 (8) | −0.10936 (9) | 0.0182 (2) | |
N1 | 0.48504 (11) | 0.33324 (9) | −0.00031 (10) | 0.0142 (2) | |
H1N | 0.535717 | 0.386282 | −0.048234 | 0.017* | |
C9 | 0.03590 (13) | 0.34783 (11) | 0.11652 (12) | 0.0159 (3) | |
H9A | 0.077065 | 0.410264 | 0.054872 | 0.019* | |
H9B | 0.038878 | 0.380120 | 0.210689 | 0.019* | |
C6 | 0.38508 (13) | 0.36508 (11) | 0.10480 (12) | 0.0131 (2) | |
C1 | 0.49639 (13) | 0.20788 (11) | −0.02167 (12) | 0.0138 (2) | |
C3 | 0.14991 (13) | 0.02619 (11) | 0.11128 (12) | 0.0165 (3) | |
H3 | 0.139093 | −0.057373 | 0.128658 | 0.020* | |
C5 | 0.13690 (13) | 0.23569 (10) | 0.10900 (12) | 0.0127 (2) | |
C4 | 0.08248 (13) | 0.11771 (11) | 0.17867 (12) | 0.0154 (3) | |
H4 | 0.015253 | 0.111223 | 0.253643 | 0.018* | |
C2 | 0.24825 (13) | 0.08589 (10) | 0.00010 (12) | 0.0143 (3) | |
H2 | 0.274586 | 0.033390 | −0.079308 | 0.017* | |
C10 | −0.13125 (14) | 0.32263 (12) | 0.07646 (14) | 0.0219 (3) | |
H10A | −0.135305 | 0.290738 | −0.016732 | 0.033* | |
H10B | −0.189111 | 0.397597 | 0.081215 | 0.033* | |
H10C | −0.174416 | 0.263710 | 0.139726 | 0.033* | |
C8 | 0.30909 (13) | 0.24969 (10) | 0.15899 (12) | 0.0127 (2) | |
H8 | 0.319697 | 0.241068 | 0.260207 | 0.015* | |
C7 | 0.38819 (13) | 0.14403 (10) | 0.07896 (12) | 0.0136 (3) | |
H7 | 0.440862 | 0.085721 | 0.140461 | 0.016* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0192 (4) | 0.0116 (4) | 0.0183 (4) | −0.0013 (3) | 0.0033 (3) | −0.0014 (3) |
O3 | 0.0160 (4) | 0.0131 (4) | 0.0120 (4) | 0.0007 (3) | 0.0017 (3) | −0.0014 (3) |
O2 | 0.0160 (4) | 0.0166 (4) | 0.0220 (4) | 0.0012 (3) | 0.0057 (3) | −0.0021 (3) |
N1 | 0.0143 (5) | 0.0117 (5) | 0.0166 (5) | −0.0017 (4) | 0.0042 (4) | 0.0009 (4) |
C9 | 0.0154 (6) | 0.0136 (6) | 0.0187 (6) | 0.0009 (4) | 0.0023 (4) | −0.0008 (5) |
C6 | 0.0126 (5) | 0.0137 (6) | 0.0131 (5) | −0.0007 (4) | −0.0011 (4) | 0.0005 (4) |
C1 | 0.0122 (5) | 0.0135 (6) | 0.0156 (6) | 0.0003 (4) | −0.0010 (4) | 0.0006 (4) |
C3 | 0.0173 (6) | 0.0121 (6) | 0.0200 (6) | −0.0035 (5) | 0.0025 (5) | 0.0010 (5) |
C5 | 0.0139 (6) | 0.0129 (6) | 0.0114 (5) | −0.0011 (4) | 0.0025 (4) | −0.0010 (4) |
C4 | 0.0150 (5) | 0.0153 (6) | 0.0159 (6) | −0.0026 (4) | 0.0035 (4) | 0.0014 (4) |
C2 | 0.0160 (6) | 0.0107 (5) | 0.0163 (6) | −0.0003 (4) | 0.0029 (4) | −0.0017 (4) |
C10 | 0.0166 (6) | 0.0207 (6) | 0.0284 (7) | 0.0015 (5) | 0.0000 (5) | 0.0003 (5) |
C8 | 0.0147 (6) | 0.0113 (5) | 0.0121 (5) | −0.0002 (4) | 0.0013 (4) | 0.0007 (4) |
C7 | 0.0145 (5) | 0.0110 (6) | 0.0152 (5) | 0.0005 (4) | 0.0018 (4) | 0.0012 (4) |
O1—C6 | 1.2198 (15) | C6—C8 | 1.5122 (15) |
O3—C5 | 1.4516 (13) | C1—C7 | 1.5174 (15) |
O3—C2 | 1.4440 (14) | C3—C4 | 1.3252 (17) |
O2—C1 | 1.2118 (14) | C3—C2 | 1.5144 (15) |
N1—C6 | 1.3764 (15) | C5—C4 | 1.5240 (15) |
N1—C1 | 1.3841 (15) | C5—C8 | 1.5781 (15) |
C9—C5 | 1.5057 (16) | C2—C7 | 1.5652 (16) |
C9—C10 | 1.5268 (16) | C8—C7 | 1.5452 (15) |
C2—O3—C5 | 96.85 (8) | C9—C5—C4 | 118.79 (10) |
C6—N1—C1 | 113.72 (9) | C9—C5—C8 | 117.36 (9) |
C5—C9—C10 | 113.36 (10) | C4—C5—C8 | 104.05 (9) |
O1—C6—N1 | 124.33 (10) | C3—C4—C5 | 106.41 (10) |
O1—C6—C8 | 127.07 (10) | O3—C2—C3 | 102.26 (9) |
N1—C6—C8 | 108.60 (9) | O3—C2—C7 | 100.52 (8) |
O2—C1—N1 | 124.28 (11) | C3—C2—C7 | 105.77 (9) |
O2—C1—C7 | 127.42 (11) | C6—C8—C5 | 112.95 (9) |
N1—C1—C7 | 108.27 (9) | C6—C8—C7 | 104.67 (9) |
C4—C3—C2 | 105.73 (10) | C7—C8—C5 | 101.49 (9) |
O3—C5—C9 | 112.24 (9) | C1—C7—C2 | 111.06 (9) |
O3—C5—C4 | 101.49 (9) | C1—C7—C8 | 104.56 (9) |
O3—C5—C8 | 100.26 (8) | C8—C7—C2 | 101.29 (9) |
C5H12O5 | F(000) = 328 |
Mr = 152.15 | Dx = 1.538 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54184 Å |
a = 8.2707 (2) Å | Cell parameters from 8709 reflections |
b = 8.9022 (2) Å | θ = 4.9–76.8° |
c = 8.9217 (2) Å | µ = 1.20 mm−1 |
V = 656.88 (3) Å3 | T = 123 K |
Z = 4 | 0.35 × 0.22 × 0.18 mm |
Agilent SuperNova Dual four-circle diffractometer with an Atlas detector | 1383 independent reflections |
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source | 1370 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.046 |
Detector resolution: 10.4391 pixels mm-1 | θmax = 76.8°, θmin = 7.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −10→11 |
Tmin = 0.383, Tmax = 1.000 | l = −11→11 |
14853 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.0779P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max = 0.001 |
S = 1.09 | Δρmax = 0.32 e Å−3 |
1383 reflections | Δρmin = −0.21 e Å−3 |
99 parameters | Absolute structure: Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.03 (7) |
Primary atom site location: dual |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.77119 (14) | 0.12974 (13) | 0.39217 (12) | 0.0196 (3) | |
H12 | 0.731315 | 0.058671 | 0.346871 | 0.029* | |
O3 | 0.68182 (14) | 0.43057 (12) | 0.46015 (12) | 0.0195 (3) | |
H13 | 0.673179 | 0.522334 | 0.459687 | 0.029* | |
O4 | 0.38520 (13) | 0.43642 (13) | 0.31715 (13) | 0.0200 (3) | |
O5 | 0.32133 (14) | 0.22866 (13) | 0.07769 (13) | 0.0198 (3) | |
H15 | 0.262808 | 0.236754 | 0.151439 | 0.030* | |
O1 | 1.08879 (14) | 0.20493 (13) | 0.28331 (13) | 0.0212 (3) | |
H11 | 1.118613 | 0.166007 | 0.361889 | 0.032* | |
C3 | 0.67256 (18) | 0.37517 (18) | 0.30950 (16) | 0.0175 (3) | |
H3 | 0.698937 | 0.457733 | 0.241076 | 0.021* | |
C4 | 0.49923 (19) | 0.32248 (18) | 0.27568 (17) | 0.0170 (3) | |
H4 | 0.476441 | 0.230237 | 0.331797 | 0.020* | |
C2 | 0.79918 (18) | 0.25174 (18) | 0.28953 (17) | 0.0174 (3) | |
H2 | 0.792172 | 0.213142 | 0.186864 | 0.021* | |
C1 | 0.96814 (19) | 0.31470 (17) | 0.31456 (19) | 0.0195 (3) | |
H1A | 0.984316 | 0.401182 | 0.250144 | 0.023* | |
H1B | 0.978498 | 0.347751 | 0.417710 | 0.023* | |
C5 | 0.47587 (19) | 0.29389 (18) | 0.10928 (17) | 0.0194 (3) | |
H5A | 0.485905 | 0.388049 | 0.055358 | 0.023* | |
H5B | 0.560241 | 0.227015 | 0.073929 | 0.023* | |
H14 | 0.353 (3) | 0.414 (3) | 0.412 (3) | 0.040 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0239 (6) | 0.0160 (5) | 0.0189 (5) | −0.0029 (4) | −0.0020 (4) | 0.0017 (4) |
O3 | 0.0249 (6) | 0.0179 (5) | 0.0157 (5) | −0.0003 (5) | −0.0001 (4) | −0.0010 (4) |
O4 | 0.0209 (5) | 0.0207 (6) | 0.0185 (5) | 0.0039 (4) | 0.0010 (4) | 0.0007 (4) |
O5 | 0.0187 (5) | 0.0242 (5) | 0.0165 (5) | −0.0020 (5) | 0.0001 (4) | −0.0011 (4) |
O1 | 0.0192 (5) | 0.0249 (6) | 0.0197 (5) | 0.0031 (5) | 0.0008 (4) | 0.0022 (5) |
C3 | 0.0193 (7) | 0.0186 (7) | 0.0145 (7) | −0.0007 (6) | −0.0002 (5) | 0.0014 (6) |
C4 | 0.0177 (6) | 0.0171 (7) | 0.0163 (7) | 0.0017 (5) | −0.0004 (6) | 0.0016 (5) |
C2 | 0.0196 (7) | 0.0185 (7) | 0.0139 (7) | −0.0002 (6) | −0.0003 (5) | 0.0020 (6) |
C1 | 0.0189 (7) | 0.0177 (7) | 0.0218 (7) | −0.0010 (6) | −0.0003 (6) | 0.0019 (6) |
C5 | 0.0182 (7) | 0.0226 (8) | 0.0174 (7) | −0.0011 (6) | −0.0002 (6) | 0.0003 (6) |
O2—H12 | 0.8200 | C3—C4 | 1.538 (2) |
O2—C2 | 1.4394 (19) | C3—C2 | 1.528 (2) |
O3—H13 | 0.8200 | C4—H4 | 0.9800 |
O3—C3 | 1.4337 (17) | C4—C5 | 1.519 (2) |
O4—C4 | 1.4336 (19) | C2—H2 | 0.9800 |
O4—H14 | 0.91 (3) | C2—C1 | 1.522 (2) |
O5—H15 | 0.8200 | C1—H1A | 0.9700 |
O5—C5 | 1.4319 (19) | C1—H1B | 0.9700 |
O1—H11 | 0.8200 | C5—H5A | 0.9700 |
O1—C1 | 1.4242 (19) | C5—H5B | 0.9700 |
C3—H3 | 0.9800 | ||
C2—O2—H12 | 109.5 | O2—C2—H2 | 108.7 |
C3—O3—H13 | 109.5 | O2—C2—C1 | 109.40 (12) |
C4—O4—H14 | 106.2 (16) | C3—C2—H2 | 108.7 |
C5—O5—H15 | 109.5 | C1—C2—C3 | 110.32 (13) |
C1—O1—H11 | 109.5 | C1—C2—H2 | 108.7 |
O3—C3—H3 | 108.3 | O1—C1—C2 | 111.22 (13) |
O3—C3—C4 | 109.79 (12) | O1—C1—H1A | 109.4 |
O3—C3—C2 | 108.66 (12) | O1—C1—H1B | 109.4 |
C4—C3—H3 | 108.3 | C2—C1—H1A | 109.4 |
C2—C3—H3 | 108.3 | C2—C1—H1B | 109.4 |
C2—C3—C4 | 113.36 (13) | H1A—C1—H1B | 108.0 |
O4—C4—C3 | 110.28 (12) | O5—C5—C4 | 111.96 (13) |
O4—C4—H4 | 109.5 | O5—C5—H5A | 109.2 |
O4—C4—C5 | 106.69 (13) | O5—C5—H5B | 109.2 |
C3—C4—H4 | 109.5 | C4—C5—H5A | 109.2 |
C5—C4—C3 | 111.18 (12) | C4—C5—H5B | 109.2 |
C5—C4—H4 | 109.5 | H5A—C5—H5B | 107.9 |
O2—C2—C3 | 110.98 (12) |
C5H6N2O2 | Dx = 1.549 Mg m−3 |
Mr = 126.12 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, Ibam | Cell parameters from 13558 reflections |
a = 13.17921 (17) Å | θ = 4.7–75.3° |
b = 13.20059 (19) Å | µ = 1.04 mm−1 |
c = 6.21502 (11) Å | T = 123 K |
V = 1081.25 (3) Å3 | Needle, clear light colourless |
Z = 8 | 0.31 × 0.07 × 0.04 mm |
F(000) = 528 |
Agilent SuperNova Dual four-circle diffractometer with an Atlas detector | 627 independent reflections |
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source | 599 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.047 |
Detector resolution: 5.2195 pixels mm-1 | θmax = 75.5°, θmin = 4.7° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −16→16 |
Tmin = 0.505, Tmax = 1.000 | l = −7→7 |
627 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0647P)2 + 0.5188P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
627 reflections | Δρmax = 0.31 e Å−3 |
62 parameters | Δρmin = −0.28 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.63511 (7) | 0.48095 (7) | 0.500000 | 0.0192 (3) | |
O1 | 0.45425 (7) | 0.77438 (7) | 0.500000 | 0.0210 (3) | |
N2 | 0.54736 (8) | 0.62905 (9) | 0.500000 | 0.0161 (3) | |
H1 | 0.492152 | 0.594313 | 0.500000 | 0.019* | |
N1 | 0.62700 (8) | 0.78643 (9) | 0.500000 | 0.0163 (3) | |
C2 | 0.63704 (10) | 0.57489 (11) | 0.500000 | 0.0156 (3) | |
C1 | 0.53713 (10) | 0.73314 (10) | 0.500000 | 0.0163 (4) | |
C3 | 0.72749 (10) | 0.63638 (10) | 0.500000 | 0.0171 (3) | |
H2 | 0.791236 | 0.606155 | 0.500000 | 0.020* | |
C4 | 0.71868 (10) | 0.73803 (10) | 0.500000 | 0.0160 (3) | |
H3 | 0.777498 | 0.776949 | 0.500000 | 0.019* | |
C5 | 0.62025 (11) | 0.89691 (11) | 0.500000 | 0.0236 (4) | |
H5 | 0.5834 (10) | 0.9191 (10) | 0.629 (2) | 0.030 (3)* | |
H4 | 0.6866 (14) | 0.9189 (14) | 0.500000 | 0.022 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0169 (5) | 0.0142 (6) | 0.0265 (6) | −0.0004 (3) | 0.000 | 0.000 |
O1 | 0.0142 (5) | 0.0188 (5) | 0.0300 (6) | 0.0018 (3) | 0.000 | 0.000 |
N2 | 0.0122 (6) | 0.0146 (6) | 0.0214 (6) | −0.0017 (4) | 0.000 | 0.000 |
N1 | 0.0149 (6) | 0.0131 (6) | 0.0208 (6) | −0.0007 (4) | 0.000 | 0.000 |
C2 | 0.0161 (7) | 0.0163 (6) | 0.0145 (6) | −0.0011 (5) | 0.000 | 0.000 |
C1 | 0.0143 (7) | 0.0179 (7) | 0.0166 (7) | −0.0010 (5) | 0.000 | 0.000 |
C3 | 0.0122 (6) | 0.0178 (7) | 0.0213 (7) | 0.0006 (5) | 0.000 | 0.000 |
C4 | 0.0124 (7) | 0.0189 (7) | 0.0166 (7) | −0.0025 (5) | 0.000 | 0.000 |
C5 | 0.0182 (7) | 0.0137 (7) | 0.0389 (9) | −0.0005 (5) | 0.000 | 0.000 |
O2—C2 | 1.2403 (18) | N1—C5 | 1.4611 (16) |
O1—C1 | 1.2204 (16) | C2—C3 | 1.4422 (18) |
N2—H1 | 0.8600 | C3—H2 | 0.9300 |
N2—C2 | 1.3813 (17) | C3—C4 | 1.3469 (19) |
N2—C1 | 1.3807 (18) | C4—H3 | 0.9300 |
N1—C1 | 1.3776 (17) | C5—H5 | 0.980 (14) |
N1—C4 | 1.3669 (17) | C5—H4 | 0.921 (19) |
C2—N2—H1 | 116.6 | N1—C1—N2 | 115.10 (11) |
C1—N2—H1 | 116.6 | C2—C3—H2 | 120.3 |
C1—N2—C2 | 126.78 (11) | C4—C3—C2 | 119.30 (12) |
C1—N1—C5 | 117.22 (11) | C4—C3—H2 | 120.3 |
C4—N1—C1 | 121.42 (12) | N1—C4—H3 | 118.6 |
C4—N1—C5 | 121.36 (11) | C3—C4—N1 | 122.82 (11) |
O2—C2—N2 | 120.00 (11) | C3—C4—H3 | 118.6 |
O2—C2—C3 | 125.42 (12) | N1—C5—H5 | 109.1 (8) |
N2—C2—C3 | 114.58 (13) | N1—C5—H4 | 104.9 (12) |
O1—C1—N2 | 122.10 (11) | H5—C5—H4 | 112.1 (10) |
O1—C1—N1 | 122.79 (12) |
C5H6N2O2 | Dx = 1.555 Mg m−3 |
Mr = 126.12 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Ibam | Cell parameters from 14193 reflections |
a = 13.1643 (1) Å | θ = 2.2–52.0° |
b = 13.1840 (2) Å | µ = 0.12 mm−1 |
c = 6.2067 (2) Å | T = 123 K |
V = 1077.22 (4) Å3 | Block |
Z = 8 | 0.41 × 0.23 × 0.14 mm |
F(000) = 528 |
Agilent SuperNova Dual four-circle diffractometer with an Atlas detector | 3266 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2580 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.056 |
Detector resolution: 16.0026 pixels mm-1 | θmax = 52.2°, θmin = 2.2° |
ω scans | h = −33→33 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −33→33 |
Tmin = 0.517, Tmax = 1.000 | l = −15→13 |
3266 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0739P)2 + 0.0821P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
3266 reflections | Δρmax = 0.78 e Å−3 |
62 parameters | Δρmin = −0.29 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.63523 (3) | 0.51908 (3) | 0.500000 | 0.01549 (8) | |
O1 | 0.45422 (3) | 0.22546 (3) | 0.500000 | 0.01730 (8) | |
N2 | 0.54722 (3) | 0.37095 (3) | 0.500000 | 0.01268 (7) | |
H1 | 0.491917 | 0.405672 | 0.500000 | 0.015* | |
N1 | 0.62703 (3) | 0.21344 (3) | 0.500000 | 0.01261 (7) | |
C1 | 0.53733 (3) | 0.26711 (4) | 0.500000 | 0.01209 (7) | |
C3 | 0.72746 (3) | 0.36378 (4) | 0.500000 | 0.01317 (8) | |
H2 | 0.791239 | 0.394113 | 0.500000 | 0.016* | |
C4 | 0.71868 (3) | 0.26175 (3) | 0.500000 | 0.01227 (7) | |
H3 | 0.777566 | 0.222777 | 0.500000 | 0.015* | |
C2 | 0.63704 (3) | 0.42505 (3) | 0.500000 | 0.01164 (7) | |
C5 | 0.62029 (4) | 0.10342 (4) | 0.500000 | 0.02022 (11) | |
H4 | 0.6883 (10) | 0.0828 (10) | 0.500000 | 0.020 (3)* | |
H5 | 0.5862 (7) | 0.0807 (7) | 0.6241 (16) | 0.028 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.01175 (12) | 0.01082 (11) | 0.0239 (2) | 0.00063 (8) | 0.000 | 0.000 |
O1 | 0.00829 (10) | 0.01549 (13) | 0.0281 (2) | −0.00171 (9) | 0.000 | 0.000 |
N2 | 0.00769 (10) | 0.01167 (12) | 0.01868 (19) | 0.00116 (8) | 0.000 | 0.000 |
N1 | 0.00852 (11) | 0.01082 (11) | 0.01848 (18) | 0.00088 (8) | 0.000 | 0.000 |
C1 | 0.00760 (12) | 0.01240 (13) | 0.01628 (19) | 0.00041 (9) | 0.000 | 0.000 |
C3 | 0.00776 (12) | 0.01254 (13) | 0.0192 (2) | 0.00031 (9) | 0.000 | 0.000 |
C4 | 0.00795 (11) | 0.01275 (14) | 0.01611 (19) | 0.00152 (9) | 0.000 | 0.000 |
C2 | 0.00884 (12) | 0.01148 (13) | 0.01460 (18) | 0.00082 (9) | 0.000 | 0.000 |
C5 | 0.01406 (17) | 0.01151 (15) | 0.0351 (4) | 0.00049 (12) | 0.000 | 0.000 |
O2—C2 | 1.2399 (6) | N1—C5 | 1.4533 (6) |
O1—C1 | 1.2242 (6) | C3—H2 | 0.9300 |
N2—H1 | 0.8600 | C3—C4 | 1.3501 (7) |
N2—C1 | 1.3752 (6) | C3—C2 | 1.4385 (6) |
N2—C2 | 1.3809 (6) | C4—H3 | 0.9300 |
N1—C1 | 1.3765 (6) | C5—H4 | 0.935 (13) |
N1—C4 | 1.3643 (6) | C5—H5 | 0.940 (10) |
C1—N2—H1 | 116.7 | C2—C3—H2 | 120.4 |
C1—N2—C2 | 126.53 (4) | N1—C4—H3 | 118.6 |
C2—N2—H1 | 116.7 | C3—C4—N1 | 122.74 (4) |
C1—N1—C5 | 117.43 (4) | C3—C4—H3 | 118.6 |
C4—N1—C1 | 121.24 (4) | O2—C2—N2 | 120.01 (4) |
C4—N1—C5 | 121.33 (4) | O2—C2—C3 | 125.26 (4) |
O1—C1—N2 | 122.08 (4) | N2—C2—C3 | 114.74 (4) |
O1—C1—N1 | 122.42 (4) | N1—C5—H4 | 103.4 (8) |
N2—C1—N1 | 115.50 (4) | N1—C5—H5 | 110.3 (6) |
C4—C3—H2 | 120.4 | H4—C5—H5 | 111.4 (7) |
C4—C3—C2 | 119.25 (4) |
C10H11NO3 | Z = 4 |
Mr = 193.20 | F(000) = 208 |
Monoclinic, P21/c | Dx = 1.412 Mg m−3 |
a = 8.6809 (6) Å | Neutron radiation, λ = 0.38- 8.8 Å |
b = 10.8826 (7) Å | µ = 4.23+ 0.0137 * lambda mm−1 |
c = 9.6214 (8) Å | T = 100 K |
β = 90.150 (9)° | Block |
V = 908.94 (11) Å3 | 5.00 × 2.00 × 1.00 mm |
SXD diffractometer | 7034 independent reflections |
Radiation source: ISIS spallation neutron source | 7034 reflections with I > 2σ(I) |
time–of–flight LAUE diffraction scans | θmax = 84.7°, θmin = 8.3° |
Absorption correction: numerical SXD2001 Gaussian numerical integration | h = −26→22 |
Tmin = 0.530, Tmax = 0.566 | k = −27→31 |
7034 measured reflections | l = −19→27 |
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)] = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.56 | (Δ/σ)max < 0.001 |
7034 reflections | Δρmax = 2.46 e Å−3 |
227 parameters | Δρmin = −2.46 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0179 (6) |
Experimental. The range of wavelengths used was 0.48-7.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. The data collection procedures on the SXD instrument used for the single crystal neutron data collection are most recently summarised in the Appendix to the following paper Wilson, C.C. (1997). J. Mol. Struct. 405, 207-217 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given _diffrn_reflns_sin(theta)/lambda_min 0.07 _diffrn_reflns_sin(theta)/lambda_max 2.09 _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electrons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 5% of Carbon _refine_diff_density_min = -4% of Carbon 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 > 2sigma(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 | 0.4962 (2) | 0.20805 (16) | −0.0216 (2) | 0.0083 (3) | |
C2 | 0.2480 (2) | 0.08601 (16) | 0.0004 (2) | 0.0090 (3) | |
H2 | 0.2756 (5) | 0.0332 (4) | −0.0938 (5) | 0.0237 (9) | |
C3 | 0.1503 (2) | 0.02552 (16) | 0.1110 (2) | 0.0107 (4) | |
C4 | 0.0818 (2) | 0.11778 (17) | 0.1793 (2) | 0.0100 (3) | |
C5 | 0.13709 (19) | 0.23578 (15) | 0.10855 (19) | 0.0067 (3) | |
C6 | 0.3853 (2) | 0.36527 (15) | 0.10469 (19) | 0.0079 (3) | |
C7 | 0.3881 (2) | 0.14395 (15) | 0.07906 (19) | 0.0076 (3) | |
H7 | 0.4500 (5) | 0.0769 (4) | 0.1423 (5) | 0.0217 (9) | |
C8 | 0.30904 (19) | 0.24944 (15) | 0.15894 (19) | 0.0066 (3) | |
H8 | 0.3154 (5) | 0.2463 (4) | 0.2723 (4) | 0.0212 (9) | |
C9 | 0.0361 (2) | 0.34814 (16) | 0.1160 (2) | 0.0102 (4) | |
H9A | 0.0834 (5) | 0.4199 (4) | 0.0496 (6) | 0.0300 (11) | |
H9B | 0.0433 (5) | 0.3833 (4) | 0.2229 (5) | 0.0275 (10) | |
C10 | −0.1313 (2) | 0.3226 (2) | 0.0765 (2) | 0.0165 (4) | |
H10A | −0.1406 (6) | 0.2884 (6) | −0.0295 (6) | 0.0442 (15) | |
H10B | −0.1991 (6) | 0.4063 (5) | 0.0827 (7) | 0.0405 (15) | |
H10C | −0.1847 (6) | 0.2554 (6) | 0.1442 (7) | 0.0442 (16) | |
N1 | 0.48544 (15) | 0.33352 (12) | −0.00041 (15) | 0.0092 (2) | |
O1 | 0.3631 (3) | 0.47004 (18) | 0.1440 (2) | 0.0106 (4) | |
O2 | 0.5774 (3) | 0.1604 (2) | −0.1094 (3) | 0.0129 (4) | |
O3 | 0.1609 (2) | 0.19477 (18) | −0.0329 (2) | 0.0084 (4) | |
H3 | 0.1500 (6) | −0.0715 (4) | 0.1332 (6) | 0.0317 (11) | |
H4 | 0.0117 (6) | 0.1149 (5) | 0.2723 (5) | 0.0287 (10) | |
H1N | 0.5480 (5) | 0.3978 (4) | −0.0566 (5) | 0.0218 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0058 (7) | 0.0086 (7) | 0.0104 (8) | 0.0017 (5) | 0.0011 (6) | −0.0017 (5) |
C2 | 0.0085 (7) | 0.0075 (7) | 0.0109 (8) | −0.0021 (6) | 0.0024 (6) | −0.0015 (5) |
H2 | 0.026 (2) | 0.023 (2) | 0.022 (2) | 0.0013 (16) | 0.0057 (18) | −0.0097 (15) |
C3 | 0.0111 (8) | 0.0068 (7) | 0.0143 (9) | −0.0012 (6) | 0.0049 (7) | 0.0006 (6) |
C4 | 0.0093 (7) | 0.0095 (7) | 0.0111 (8) | −0.0024 (6) | 0.0035 (7) | 0.0013 (6) |
C5 | 0.0061 (6) | 0.0062 (6) | 0.0077 (7) | −0.0010 (5) | 0.0014 (6) | 0.0011 (5) |
C6 | 0.0077 (7) | 0.0064 (6) | 0.0096 (8) | 0.0001 (5) | 0.0008 (6) | −0.0013 (5) |
C7 | 0.0070 (7) | 0.0061 (6) | 0.0096 (8) | 0.0008 (5) | 0.0002 (6) | 0.0013 (5) |
H7 | 0.0202 (18) | 0.0197 (18) | 0.025 (2) | 0.0050 (14) | −0.0011 (17) | 0.0075 (14) |
C8 | 0.0052 (6) | 0.0077 (7) | 0.0068 (7) | −0.0014 (5) | 0.0007 (6) | 0.0005 (5) |
H8 | 0.027 (2) | 0.0228 (19) | 0.0138 (18) | −0.0019 (15) | −0.0025 (17) | 0.0027 (14) |
C9 | 0.0072 (7) | 0.0090 (7) | 0.0144 (9) | 0.0019 (5) | 0.0007 (7) | −0.0014 (6) |
H9A | 0.023 (2) | 0.024 (2) | 0.042 (3) | −0.0005 (16) | 0.002 (2) | 0.0119 (19) |
H9B | 0.025 (2) | 0.031 (2) | 0.026 (2) | 0.0049 (17) | −0.0022 (19) | −0.0140 (18) |
C10 | 0.0066 (7) | 0.0200 (10) | 0.0228 (11) | 0.0018 (6) | −0.0020 (8) | −0.0009 (8) |
H10A | 0.028 (3) | 0.066 (4) | 0.038 (3) | −0.002 (3) | −0.009 (2) | −0.017 (3) |
H10B | 0.023 (2) | 0.039 (3) | 0.059 (4) | 0.014 (2) | −0.006 (3) | −0.006 (3) |
H10C | 0.024 (2) | 0.053 (4) | 0.056 (4) | −0.009 (2) | 0.003 (3) | 0.023 (3) |
N1 | 0.0074 (5) | 0.0085 (5) | 0.0117 (6) | −0.0014 (4) | 0.0035 (5) | 0.0003 (4) |
O1 | 0.0119 (9) | 0.0070 (8) | 0.0129 (10) | −0.0018 (6) | 0.0048 (8) | −0.0011 (7) |
O2 | 0.0115 (9) | 0.0113 (9) | 0.0160 (11) | 0.0007 (7) | 0.0049 (8) | −0.0012 (7) |
O3 | 0.0079 (8) | 0.0115 (8) | 0.0056 (8) | −0.0004 (6) | 0.0000 (7) | −0.0003 (6) |
H3 | 0.041 (3) | 0.0117 (18) | 0.042 (3) | −0.0014 (17) | 0.012 (2) | 0.0052 (16) |
H4 | 0.033 (2) | 0.030 (2) | 0.023 (2) | −0.0030 (19) | 0.013 (2) | 0.0030 (17) |
H1N | 0.0213 (18) | 0.0157 (17) | 0.028 (2) | −0.0038 (14) | 0.0083 (18) | 0.0040 (15) |
C1—O2 | 1.217 (3) | C5—O3 | 1.448 (3) |
C1—N1 | 1.384 (2) | C5—C9 | 1.506 (2) |
C1—C7 | 1.520 (3) | C5—C8 | 1.575 (2) |
C2—O3 | 1.440 (3) | C6—O1 | 1.217 (3) |
C2—C3 | 1.513 (3) | C6—N1 | 1.379 (3) |
C2—C7 | 1.564 (2) | C6—C8 | 1.517 (3) |
C3—C4 | 1.340 (3) | C7—C8 | 1.544 (3) |
C4—C5 | 1.531 (3) | C9—C10 | 1.526 (2) |
O2—C1—N1 | 124.2 (2) | C4—C5—C8 | 103.92 (12) |
O2—C1—C7 | 127.33 (19) | O1—C6—N1 | 124.3 (2) |
N1—C1—C7 | 108.48 (16) | O1—C6—C8 | 127.0 (2) |
O3—C2—C3 | 102.64 (17) | N1—C6—C8 | 108.70 (14) |
O3—C2—C7 | 100.58 (13) | C1—C7—C8 | 104.59 (14) |
C3—C2—C7 | 105.75 (15) | C1—C7—C2 | 110.91 (15) |
C4—C3—C2 | 105.61 (16) | C8—C7—C2 | 101.22 (13) |
C3—C4—C5 | 105.69 (18) | C6—C8—C7 | 104.57 (16) |
O3—C5—C9 | 112.29 (14) | C6—C8—C5 | 112.75 (12) |
O3—C5—C4 | 101.82 (15) | C7—C8—C5 | 101.46 (12) |
C9—C5—C4 | 118.44 (17) | C5—C9—C10 | 113.21 (15) |
O3—C5—C8 | 100.44 (15) | C6—N1—C1 | 113.46 (15) |
C9—C5—C8 | 117.38 (13) | C2—O3—C5 | 96.92 (15) |
Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register