Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616019405/gw5049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo2_0msup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo140_0msup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo142_0msup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo143_0msup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo150_0msup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo200_0msup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049mo_in4meo250_0msup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616019405/gw5049in4meo3_0msup9.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520616019405/gw5049in4meo3_0msup10.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616019405/gw5049sup11.pdf |
CCDC references: 1495125; 1495126; 1495127; 1495128; 1495129; 1495130; 1495131; 1495132
For all compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae, 2006); software used to prepare material for publication: PLATON (Spek, 2009).
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.398 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.333 (2) Å | Cell parameters from 4328 reflections |
b = 5.1356 (5) Å | θ = 2.6–28.3° |
c = 24.966 (2) Å | µ = 0.10 mm−1 |
β = 90.909 (6)° | T = 100 K |
V = 2606.7 (4) Å3 | Plate, colourless |
Z = 8 | 0.55 × 0.19 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3212 independent reflections |
Radiation source: fine-focus sealed tube | 2619 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −26→26 |
Tmin = 0.899, Tmax = 0.970 | k = −6→6 |
13967 measured reflections | l = −32→30 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0675P)2 + 1.2363P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3212 reflections | Δρmax = 0.37 e Å−3 |
194 parameters | Δρmin = −0.21 e Å−3 |
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 | 0.99868 (4) | 1.24213 (16) | 0.54425 (3) | 0.0183 (2) | |
O2 | 0.77882 (4) | 0.16286 (16) | 0.64553 (3) | 0.0183 (2) | |
O3 | 0.70539 (4) | 0.22808 (16) | 0.57895 (3) | 0.0185 (2) | |
O4 | 0.56123 (4) | −0.66208 (17) | 0.70969 (3) | 0.0209 (2) | |
N1 | 0.83993 (5) | 0.56083 (19) | 0.59967 (4) | 0.0175 (2) | |
N2 | 0.91705 (5) | 1.32472 (19) | 0.48424 (4) | 0.0162 (2) | |
C1 | 0.93334 (6) | 0.8427 (2) | 0.59283 (5) | 0.0187 (2) | |
H1A | 0.9756 | 0.8924 | 0.6060 | 0.022* | |
C2 | 0.89927 (6) | 0.6406 (2) | 0.61675 (5) | 0.0201 (3) | |
H2A | 0.9190 | 0.5549 | 0.6466 | 0.024* | |
C3 | 0.81249 (6) | 0.6854 (2) | 0.55783 (5) | 0.0183 (2) | |
H3A | 0.7703 | 0.6306 | 0.5454 | 0.022* | |
C4 | 0.84284 (5) | 0.8914 (2) | 0.53165 (5) | 0.0171 (2) | |
H4A | 0.8216 | 0.9755 | 0.5022 | 0.021* | |
C5 | 0.90470 (5) | 0.9714 (2) | 0.54940 (4) | 0.0144 (2) | |
C6 | 0.94369 (5) | 1.1914 (2) | 0.52493 (4) | 0.0143 (2) | |
C7 | 0.68311 (5) | −0.1004 (2) | 0.64401 (4) | 0.0153 (2) | |
C8 | 0.70751 (6) | −0.2547 (2) | 0.68563 (5) | 0.0173 (2) | |
H8A | 0.7513 | −0.2288 | 0.6984 | 0.021* | |
C9 | 0.66862 (5) | −0.4474 (2) | 0.70886 (5) | 0.0180 (2) | |
H9A | 0.6856 | −0.5516 | 0.7373 | 0.022* | |
C10 | 0.60456 (6) | −0.4846 (2) | 0.68973 (4) | 0.0169 (2) | |
C11 | 0.58026 (6) | −0.3347 (2) | 0.64713 (5) | 0.0190 (3) | |
H11A | 0.5369 | −0.3634 | 0.6337 | 0.023* | |
C12 | 0.61909 (6) | −0.1452 (2) | 0.62452 (5) | 0.0178 (2) | |
H12A | 0.6023 | −0.0442 | 0.5955 | 0.021* | |
C13 | 0.72290 (5) | 0.1110 (2) | 0.61966 (4) | 0.0153 (2) | |
C14 | 0.58192 (6) | −0.8108 (3) | 0.75519 (5) | 0.0234 (3) | |
H14A | 0.5460 | −0.9247 | 0.7663 | 0.035* | |
H14B | 0.5939 | −0.6929 | 0.7846 | 0.035* | |
H14C | 0.6201 | −0.9169 | 0.7459 | 0.035* | |
H1N2 | 0.9418 (8) | 1.458 (3) | 0.4703 (6) | 0.034 (4)* | |
H2N2 | 0.8766 (8) | 1.285 (3) | 0.4689 (6) | 0.032 (4)* | |
H1O2 | 0.8018 (10) | 0.309 (4) | 0.6276 (7) | 0.058 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0159 (4) | 0.0188 (4) | 0.0200 (4) | −0.0033 (3) | −0.0026 (3) | 0.0024 (3) |
O2 | 0.0167 (4) | 0.0194 (4) | 0.0186 (4) | −0.0041 (3) | −0.0020 (3) | 0.0032 (3) |
O3 | 0.0185 (4) | 0.0197 (4) | 0.0173 (4) | −0.0017 (3) | −0.0009 (3) | 0.0034 (3) |
O4 | 0.0183 (4) | 0.0222 (4) | 0.0223 (4) | −0.0053 (3) | 0.0007 (3) | 0.0062 (3) |
N1 | 0.0174 (5) | 0.0165 (5) | 0.0187 (5) | −0.0004 (4) | 0.0024 (4) | 0.0005 (4) |
N2 | 0.0161 (5) | 0.0156 (5) | 0.0170 (5) | −0.0022 (4) | −0.0009 (4) | 0.0022 (4) |
C1 | 0.0143 (5) | 0.0213 (6) | 0.0203 (6) | −0.0025 (4) | −0.0016 (4) | 0.0026 (5) |
C2 | 0.0192 (6) | 0.0214 (6) | 0.0196 (6) | 0.0000 (5) | −0.0010 (4) | 0.0057 (5) |
C3 | 0.0160 (5) | 0.0194 (6) | 0.0196 (6) | −0.0020 (4) | 0.0007 (4) | −0.0005 (4) |
C4 | 0.0172 (5) | 0.0180 (6) | 0.0162 (5) | 0.0006 (4) | −0.0006 (4) | 0.0015 (4) |
C5 | 0.0151 (5) | 0.0138 (5) | 0.0143 (5) | 0.0004 (4) | 0.0029 (4) | −0.0010 (4) |
C6 | 0.0148 (5) | 0.0143 (5) | 0.0139 (5) | −0.0004 (4) | 0.0017 (4) | −0.0019 (4) |
C7 | 0.0155 (5) | 0.0161 (5) | 0.0143 (5) | −0.0014 (4) | 0.0012 (4) | −0.0008 (4) |
C8 | 0.0163 (5) | 0.0183 (6) | 0.0174 (6) | −0.0014 (4) | −0.0006 (4) | −0.0005 (4) |
C9 | 0.0190 (5) | 0.0182 (6) | 0.0169 (6) | −0.0004 (4) | −0.0014 (4) | 0.0020 (4) |
C10 | 0.0188 (5) | 0.0161 (5) | 0.0158 (5) | −0.0025 (4) | 0.0035 (4) | −0.0006 (4) |
C11 | 0.0150 (5) | 0.0222 (6) | 0.0197 (6) | −0.0032 (4) | −0.0012 (4) | 0.0005 (5) |
C12 | 0.0177 (5) | 0.0197 (6) | 0.0160 (5) | −0.0006 (4) | −0.0008 (4) | 0.0015 (4) |
C13 | 0.0143 (5) | 0.0158 (5) | 0.0159 (5) | −0.0004 (4) | 0.0013 (4) | −0.0012 (4) |
C14 | 0.0248 (6) | 0.0232 (6) | 0.0223 (6) | −0.0035 (5) | 0.0014 (5) | 0.0074 (5) |
O1—C6 | 1.2385 (14) | C4—C5 | 1.3891 (15) |
O2—C13 | 1.3256 (14) | C4—H4A | 0.9500 |
O2—H1O2 | 0.99 (2) | C5—C6 | 1.5144 (15) |
O3—C13 | 1.2286 (14) | C7—C8 | 1.3919 (16) |
O4—C10 | 1.3671 (14) | C7—C12 | 1.4014 (16) |
O4—C14 | 1.4267 (14) | C7—C13 | 1.4898 (15) |
N1—C2 | 1.3376 (15) | C8—C9 | 1.3984 (16) |
N1—C3 | 1.3389 (15) | C8—H8A | 0.9500 |
N2—C6 | 1.3329 (15) | C9—C10 | 1.3932 (16) |
N2—H1N2 | 0.923 (17) | C9—H9A | 0.9500 |
N2—H2N2 | 0.924 (18) | C10—C11 | 1.3967 (16) |
C1—C2 | 1.3883 (16) | C11—C12 | 1.3797 (16) |
C1—C5 | 1.3898 (16) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C14—H14A | 0.9800 |
C3—C4 | 1.3931 (16) | C14—H14B | 0.9800 |
C3—H3A | 0.9500 | C14—H14C | 0.9800 |
C13—O2—H1O2 | 109.8 (11) | C12—C7—C13 | 119.04 (10) |
C10—O4—C14 | 117.61 (9) | C7—C8—C9 | 121.01 (11) |
C2—N1—C3 | 117.71 (10) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 116.8 (10) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 123.3 (10) | C10—C9—C8 | 119.12 (11) |
H1N2—N2—H2N2 | 119.9 (14) | C10—C9—H9A | 120.4 |
C2—C1—C5 | 119.03 (10) | C8—C9—H9A | 120.4 |
C2—C1—H1A | 120.5 | O4—C10—C9 | 124.80 (10) |
C5—C1—H1A | 120.5 | O4—C10—C11 | 115.01 (10) |
N1—C2—C1 | 123.07 (11) | C9—C10—C11 | 120.19 (10) |
N1—C2—H2A | 118.5 | C12—C11—C10 | 120.17 (10) |
C1—C2—H2A | 118.5 | C12—C11—H11A | 119.9 |
N1—C3—C4 | 123.14 (11) | C10—C11—H11A | 119.9 |
N1—C3—H3A | 118.4 | C11—C12—C7 | 120.53 (11) |
C4—C3—H3A | 118.4 | C11—C12—H12A | 119.7 |
C5—C4—C3 | 118.72 (11) | C7—C12—H12A | 119.7 |
C5—C4—H4A | 120.6 | O3—C13—O2 | 122.68 (10) |
C3—C4—H4A | 120.6 | O3—C13—C7 | 122.82 (10) |
C4—C5—C1 | 118.32 (10) | O2—C13—C7 | 114.50 (10) |
C4—C5—C6 | 124.68 (10) | O4—C14—H14A | 109.5 |
C1—C5—C6 | 117.00 (10) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 122.84 (10) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.35 (10) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.80 (10) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.94 (10) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 122.01 (10) | ||
C3—N1—C2—C1 | −0.65 (18) | C7—C8—C9—C10 | 0.14 (17) |
C5—C1—C2—N1 | 0.63 (19) | C14—O4—C10—C9 | 3.41 (17) |
C2—N1—C3—C4 | 0.13 (17) | C14—O4—C10—C11 | −176.55 (10) |
N1—C3—C4—C5 | 0.38 (18) | C8—C9—C10—O4 | −178.56 (11) |
C3—C4—C5—C1 | −0.38 (17) | C8—C9—C10—C11 | 1.40 (17) |
C3—C4—C5—C6 | 179.87 (10) | O4—C10—C11—C12 | 178.55 (10) |
C2—C1—C5—C4 | −0.09 (17) | C9—C10—C11—C12 | −1.42 (18) |
C2—C1—C5—C6 | 179.68 (10) | C10—C11—C12—C7 | −0.12 (18) |
C4—C5—C6—O1 | −179.37 (11) | C8—C7—C12—C11 | 1.64 (17) |
C1—C5—C6—O1 | 0.88 (15) | C13—C7—C12—C11 | −178.24 (10) |
C4—C5—C6—N2 | 1.75 (16) | C8—C7—C13—O3 | 171.05 (11) |
C1—C5—C6—N2 | −178.00 (10) | C12—C7—C13—O3 | −9.07 (17) |
C12—C7—C8—C9 | −1.65 (17) | C8—C7—C13—O2 | −8.99 (16) |
C13—C7—C8—C9 | 178.23 (10) | C12—C7—C13—O2 | 170.89 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.921 (16) | 1.996 (16) | 2.9033 (13) | 168.2 (13) |
N2—H2N2···O3ii | 0.925 (16) | 2.056 (16) | 2.9679 (13) | 168.4 (13) |
O2—H1O2···N1 | 0.99 (2) | 1.67 (2) | 2.6603 (13) | 177.8 (16) |
C3—H3A···O3 | 0.95 | 2.60 | 3.2516 (14) | 126 |
C4—H4A···O3ii | 0.95 | 2.46 | 3.3897 (14) | 166 |
C11—H11A···O1iii | 0.95 | 2.43 | 3.0724 (15) | 124 |
C14—H14A···O4iv | 0.98 | 2.58 | 3.5463 (16) | 170 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z; (iv) −x+1, y−1/2, −z+3/2. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.396 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.332 (2) Å | Cell parameters from 4959 reflections |
b = 5.1318 (5) Å | θ = 2.6–28.6° |
c = 25.024 (2) Å | µ = 0.10 mm−1 |
β = 90.917 (6)° | T = 140 K |
V = 2610.7 (4) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3345 independent reflections |
Radiation source: fine-focus sealed tube | 2666 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 28.7°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −27→27 |
Tmin = 0.890, Tmax = 0.969 | k = −6→6 |
20244 measured reflections | l = −33→33 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0688P)2 + 0.9686P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
3345 reflections | Δρmax = 0.31 e Å−3 |
194 parameters | Δρmin = −0.23 e Å−3 |
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 | 0.99841 (4) | 1.24270 (16) | 0.54442 (3) | 0.0227 (2) | |
O2 | 0.77833 (4) | 0.16352 (17) | 0.64538 (3) | 0.0226 (2) | |
O3 | 0.70513 (4) | 0.22785 (17) | 0.57897 (3) | 0.0232 (2) | |
O4 | 0.56136 (4) | −0.66036 (17) | 0.70993 (3) | 0.0265 (2) | |
N1 | 0.83978 (5) | 0.56190 (19) | 0.59969 (4) | 0.0219 (2) | |
N2 | 0.91723 (5) | 1.3239 (2) | 0.48434 (4) | 0.0200 (2) | |
C1 | 0.93304 (6) | 0.8441 (2) | 0.59301 (5) | 0.0234 (3) | |
H1A | 0.9752 | 0.8944 | 0.6063 | 0.028* | |
C2 | 0.89896 (6) | 0.6423 (2) | 0.61673 (5) | 0.0253 (3) | |
H2A | 0.9187 | 0.5569 | 0.6466 | 0.030* | |
C3 | 0.81256 (6) | 0.6860 (2) | 0.55788 (5) | 0.0225 (3) | |
H3A | 0.7704 | 0.6312 | 0.5454 | 0.027* | |
C4 | 0.84292 (6) | 0.8914 (2) | 0.53173 (5) | 0.0209 (2) | |
H4A | 0.8218 | 0.9751 | 0.5022 | 0.025* | |
C5 | 0.90462 (5) | 0.9717 (2) | 0.54954 (4) | 0.0176 (2) | |
C6 | 0.94362 (5) | 1.1915 (2) | 0.52507 (4) | 0.0176 (2) | |
C7 | 0.68289 (5) | −0.0999 (2) | 0.64394 (4) | 0.0187 (2) | |
C8 | 0.70728 (6) | −0.2530 (2) | 0.68565 (5) | 0.0216 (3) | |
H8A | 0.7510 | −0.2264 | 0.6985 | 0.026* | |
C9 | 0.66851 (6) | −0.4452 (2) | 0.70898 (5) | 0.0224 (3) | |
H9A | 0.6856 | −0.5485 | 0.7375 | 0.027* | |
C10 | 0.60467 (6) | −0.4835 (2) | 0.68993 (4) | 0.0206 (2) | |
C11 | 0.58038 (6) | −0.3344 (2) | 0.64723 (5) | 0.0237 (3) | |
H11A | 0.5370 | −0.3636 | 0.6338 | 0.028* | |
C12 | 0.61899 (6) | −0.1455 (2) | 0.62455 (5) | 0.0222 (3) | |
H12A | 0.6021 | −0.0452 | 0.5955 | 0.027* | |
C13 | 0.72257 (5) | 0.1115 (2) | 0.61961 (4) | 0.0189 (2) | |
C14 | 0.58195 (7) | −0.8080 (3) | 0.75547 (5) | 0.0309 (3) | |
H14A | 0.5460 | −0.9219 | 0.7666 | 0.046* | |
H14B | 0.5938 | −0.6894 | 0.7848 | 0.046* | |
H14C | 0.6202 | −0.9142 | 0.7463 | 0.046* | |
H1N2 | 0.9415 (8) | 1.460 (3) | 0.4713 (6) | 0.040 (4)* | |
H2N2 | 0.8771 (8) | 1.280 (3) | 0.4692 (6) | 0.034 (4)* | |
H1O2 | 0.8007 (10) | 0.307 (4) | 0.6289 (7) | 0.063 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0189 (4) | 0.0242 (4) | 0.0249 (4) | −0.0050 (3) | −0.0046 (3) | 0.0031 (3) |
O2 | 0.0186 (4) | 0.0254 (4) | 0.0237 (4) | −0.0055 (3) | −0.0041 (3) | 0.0045 (3) |
O3 | 0.0217 (4) | 0.0253 (4) | 0.0224 (4) | −0.0027 (3) | −0.0030 (3) | 0.0052 (3) |
O4 | 0.0225 (4) | 0.0282 (5) | 0.0288 (5) | −0.0070 (4) | 0.0004 (3) | 0.0075 (4) |
N1 | 0.0201 (5) | 0.0213 (5) | 0.0241 (5) | −0.0013 (4) | 0.0012 (4) | 0.0021 (4) |
N2 | 0.0182 (5) | 0.0193 (5) | 0.0225 (5) | −0.0027 (4) | −0.0028 (4) | 0.0028 (4) |
C1 | 0.0171 (5) | 0.0269 (6) | 0.0261 (6) | −0.0030 (5) | −0.0041 (4) | 0.0045 (5) |
C2 | 0.0228 (6) | 0.0275 (6) | 0.0256 (6) | −0.0008 (5) | −0.0031 (5) | 0.0082 (5) |
C3 | 0.0189 (6) | 0.0240 (6) | 0.0247 (6) | −0.0033 (5) | −0.0004 (4) | 0.0009 (5) |
C4 | 0.0192 (5) | 0.0229 (6) | 0.0205 (5) | −0.0008 (4) | −0.0019 (4) | 0.0026 (4) |
C5 | 0.0173 (5) | 0.0166 (5) | 0.0190 (5) | 0.0001 (4) | 0.0018 (4) | −0.0008 (4) |
C6 | 0.0174 (5) | 0.0172 (5) | 0.0182 (5) | −0.0003 (4) | 0.0004 (4) | −0.0019 (4) |
C7 | 0.0176 (5) | 0.0198 (5) | 0.0188 (5) | −0.0019 (4) | 0.0005 (4) | −0.0005 (4) |
C8 | 0.0189 (5) | 0.0228 (6) | 0.0229 (6) | −0.0020 (4) | −0.0024 (4) | 0.0010 (4) |
C9 | 0.0224 (6) | 0.0228 (6) | 0.0221 (6) | −0.0014 (4) | −0.0025 (4) | 0.0037 (4) |
C10 | 0.0211 (6) | 0.0204 (5) | 0.0204 (5) | −0.0031 (4) | 0.0028 (4) | −0.0001 (4) |
C11 | 0.0173 (5) | 0.0290 (6) | 0.0245 (6) | −0.0039 (5) | −0.0029 (4) | 0.0024 (5) |
C12 | 0.0199 (6) | 0.0262 (6) | 0.0206 (5) | −0.0012 (5) | −0.0028 (4) | 0.0035 (5) |
C13 | 0.0166 (5) | 0.0205 (5) | 0.0195 (5) | −0.0001 (4) | 0.0004 (4) | −0.0008 (4) |
C14 | 0.0321 (7) | 0.0310 (7) | 0.0297 (7) | −0.0061 (5) | 0.0023 (5) | 0.0108 (5) |
O1—C6 | 1.2359 (14) | C4—C5 | 1.3872 (15) |
O2—C13 | 1.3224 (14) | C4—H4A | 0.9500 |
O2—H1O2 | 0.96 (2) | C5—C6 | 1.5139 (15) |
O3—C13 | 1.2268 (14) | C7—C8 | 1.3916 (16) |
O4—C10 | 1.3652 (14) | C7—C12 | 1.3993 (16) |
O4—C14 | 1.4257 (15) | C7—C13 | 1.4881 (16) |
N1—C2 | 1.3356 (15) | C8—C9 | 1.3963 (16) |
N1—C3 | 1.3373 (15) | C8—H8A | 0.9500 |
N2—C6 | 1.3308 (14) | C9—C10 | 1.3894 (16) |
N2—H1N2 | 0.920 (18) | C9—H9A | 0.9500 |
N2—H2N2 | 0.921 (17) | C10—C11 | 1.3982 (16) |
C1—C2 | 1.3850 (17) | C11—C12 | 1.3756 (17) |
C1—C5 | 1.3874 (15) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C14—H14A | 0.9800 |
C3—C4 | 1.3903 (17) | C14—H14B | 0.9800 |
C3—H3A | 0.9500 | C14—H14C | 0.9800 |
C13—O2—H1O2 | 110.7 (12) | C12—C7—C13 | 119.11 (10) |
C10—O4—C14 | 117.60 (10) | C7—C8—C9 | 121.05 (11) |
C2—N1—C3 | 117.53 (10) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 116.7 (10) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 122.3 (10) | C10—C9—C8 | 119.14 (11) |
H1N2—N2—H2N2 | 121.0 (14) | C10—C9—H9A | 120.4 |
C2—C1—C5 | 118.94 (11) | C8—C9—H9A | 120.4 |
C2—C1—H1A | 120.5 | O4—C10—C9 | 124.94 (10) |
C5—C1—H1A | 120.5 | O4—C10—C11 | 114.96 (10) |
N1—C2—C1 | 123.27 (11) | C9—C10—C11 | 120.09 (10) |
N1—C2—H2A | 118.4 | C12—C11—C10 | 120.27 (11) |
C1—C2—H2A | 118.4 | C12—C11—H11A | 119.9 |
N1—C3—C4 | 123.23 (11) | C10—C11—H11A | 119.9 |
N1—C3—H3A | 118.4 | C11—C12—C7 | 120.51 (11) |
C4—C3—H3A | 118.4 | C11—C12—H12A | 119.7 |
C5—C4—C3 | 118.68 (10) | C7—C12—H12A | 119.7 |
C5—C4—H4A | 120.7 | O3—C13—O2 | 122.71 (10) |
C3—C4—H4A | 120.7 | O3—C13—C7 | 122.85 (10) |
C4—C5—C1 | 118.36 (10) | O2—C13—C7 | 114.44 (10) |
C4—C5—C6 | 124.61 (10) | O4—C14—H14A | 109.5 |
C1—C5—C6 | 117.02 (10) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 122.77 (10) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.33 (10) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.89 (10) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.90 (10) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 121.98 (10) | ||
C3—N1—C2—C1 | −0.59 (19) | C7—C8—C9—C10 | 0.19 (18) |
C5—C1—C2—N1 | 0.4 (2) | C14—O4—C10—C9 | 3.28 (18) |
C2—N1—C3—C4 | 0.23 (18) | C14—O4—C10—C11 | −176.51 (11) |
N1—C3—C4—C5 | 0.30 (19) | C8—C9—C10—O4 | −178.51 (11) |
C3—C4—C5—C1 | −0.46 (17) | C8—C9—C10—C11 | 1.28 (18) |
C3—C4—C5—C6 | 179.90 (10) | O4—C10—C11—C12 | 178.49 (11) |
C2—C1—C5—C4 | 0.13 (18) | C9—C10—C11—C12 | −1.32 (19) |
C2—C1—C5—C6 | 179.79 (10) | C10—C11—C12—C7 | −0.13 (19) |
C4—C5—C6—O1 | −179.41 (11) | C8—C7—C12—C11 | 1.56 (18) |
C1—C5—C6—O1 | 0.95 (16) | C13—C7—C12—C11 | −178.09 (11) |
C4—C5—C6—N2 | 1.65 (17) | C8—C7—C13—O3 | 171.19 (11) |
C1—C5—C6—N2 | −177.99 (10) | C12—C7—C13—O3 | −9.16 (17) |
C12—C7—C8—C9 | −1.60 (18) | C8—C7—C13—O2 | −8.70 (16) |
C13—C7—C8—C9 | 178.05 (11) | C12—C7—C13—O2 | 170.95 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.918 (16) | 1.998 (16) | 2.9062 (13) | 170.0 (14) |
N2—H2N2···O3ii | 0.922 (16) | 2.063 (16) | 2.9692 (13) | 167.3 (13) |
O2—H1O2···N1 | 0.96 (2) | 1.70 (2) | 2.6634 (13) | 180 (2) |
C4—H4A···O3ii | 0.95 | 2.46 | 3.3945 (15) | 166 |
C11—H11A···O1iii | 0.95 | 2.44 | 3.0791 (15) | 125 |
C14—H14A···O4iv | 0.98 | 2.58 | 3.5483 (17) | 170 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z; (iv) −x+1, y−1/2, −z+3/2. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.401 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.296 (7) Å | Cell parameters from 3184 reflections |
b = 5.1263 (18) Å | θ = 2.6–28.7° |
c = 25.005 (9) Å | µ = 0.10 mm−1 |
β = 90.95 (2)° | T = 142 K |
V = 2601.2 (16) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3363 independent reflections |
Radiation source: fine-focus sealed tube | 2502 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 28.8°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −27→27 |
Tmin = 0.769, Tmax = 0.969 | k = −6→6 |
14782 measured reflections | l = −33→33 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.7112P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3363 reflections | Δρmax = 0.31 e Å−3 |
194 parameters | Δρmin = −0.24 e Å−3 |
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 | 0.99842 (5) | 1.24307 (18) | 0.54447 (4) | 0.0241 (2) | |
O2 | 0.77837 (5) | 0.16395 (19) | 0.64536 (4) | 0.0236 (2) | |
O3 | 0.70514 (5) | 0.22770 (19) | 0.57901 (4) | 0.0240 (2) | |
O4 | 0.56137 (5) | −0.66005 (19) | 0.70995 (4) | 0.0278 (3) | |
N1 | 0.83976 (5) | 0.5619 (2) | 0.59967 (4) | 0.0230 (3) | |
N2 | 0.91727 (6) | 1.3243 (2) | 0.48431 (4) | 0.0209 (3) | |
C1 | 0.93303 (7) | 0.8442 (3) | 0.59299 (5) | 0.0245 (3) | |
H1A | 0.9752 | 0.8948 | 0.6063 | 0.029* | |
C2 | 0.89904 (7) | 0.6425 (3) | 0.61675 (6) | 0.0266 (3) | |
H2A | 0.9188 | 0.5571 | 0.6467 | 0.032* | |
C3 | 0.81270 (7) | 0.6861 (3) | 0.55785 (6) | 0.0233 (3) | |
H3A | 0.7705 | 0.6312 | 0.5453 | 0.028* | |
C4 | 0.84303 (6) | 0.8913 (3) | 0.53178 (5) | 0.0220 (3) | |
H4A | 0.8219 | 0.9751 | 0.5023 | 0.026* | |
C5 | 0.90473 (6) | 0.9715 (2) | 0.54952 (5) | 0.0184 (3) | |
C6 | 0.94349 (6) | 1.1916 (2) | 0.52509 (5) | 0.0185 (3) | |
C7 | 0.68298 (6) | −0.0997 (3) | 0.64400 (5) | 0.0197 (3) | |
C8 | 0.70712 (7) | −0.2528 (3) | 0.68567 (5) | 0.0227 (3) | |
H8A | 0.7509 | −0.2259 | 0.6986 | 0.027* | |
C9 | 0.66850 (6) | −0.4450 (3) | 0.70898 (5) | 0.0236 (3) | |
H9A | 0.6856 | −0.5484 | 0.7375 | 0.028* | |
C10 | 0.60455 (6) | −0.4834 (3) | 0.68986 (5) | 0.0216 (3) | |
C11 | 0.58037 (7) | −0.3342 (3) | 0.64727 (5) | 0.0246 (3) | |
H11A | 0.5369 | −0.3630 | 0.6339 | 0.030* | |
C12 | 0.61906 (7) | −0.1458 (3) | 0.62461 (5) | 0.0232 (3) | |
H12A | 0.6022 | −0.0458 | 0.5955 | 0.028* | |
C13 | 0.72263 (6) | 0.1115 (3) | 0.61959 (5) | 0.0200 (3) | |
C14 | 0.58194 (8) | −0.8078 (3) | 0.75548 (6) | 0.0314 (3) | |
H14A | 0.5461 | −0.9236 | 0.7663 | 0.047* | |
H14B | 0.5932 | −0.6892 | 0.7850 | 0.047* | |
H14C | 0.6207 | −0.9122 | 0.7465 | 0.047* | |
H1N2 | 0.9417 (8) | 1.463 (4) | 0.4713 (7) | 0.039 (5)* | |
H2N2 | 0.8764 (9) | 1.280 (4) | 0.4704 (7) | 0.039 (5)* | |
H1O2 | 0.8013 (11) | 0.309 (4) | 0.6281 (8) | 0.068 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0209 (5) | 0.0240 (5) | 0.0271 (5) | −0.0049 (4) | −0.0056 (4) | 0.0024 (4) |
O2 | 0.0211 (5) | 0.0248 (5) | 0.0247 (5) | −0.0056 (4) | −0.0048 (4) | 0.0042 (4) |
O3 | 0.0235 (5) | 0.0257 (5) | 0.0227 (5) | −0.0022 (4) | −0.0033 (4) | 0.0053 (4) |
O4 | 0.0249 (5) | 0.0288 (5) | 0.0296 (6) | −0.0069 (4) | −0.0006 (4) | 0.0081 (4) |
N1 | 0.0222 (6) | 0.0211 (6) | 0.0256 (6) | −0.0016 (5) | 0.0006 (4) | 0.0016 (5) |
N2 | 0.0200 (6) | 0.0195 (6) | 0.0229 (6) | −0.0031 (4) | −0.0032 (4) | 0.0033 (4) |
C1 | 0.0190 (6) | 0.0278 (7) | 0.0265 (7) | −0.0031 (5) | −0.0053 (5) | 0.0051 (6) |
C2 | 0.0250 (7) | 0.0277 (7) | 0.0269 (7) | −0.0001 (6) | −0.0037 (6) | 0.0079 (6) |
C3 | 0.0199 (6) | 0.0246 (7) | 0.0251 (7) | −0.0026 (5) | −0.0019 (5) | 0.0002 (5) |
C4 | 0.0215 (6) | 0.0228 (7) | 0.0215 (7) | −0.0009 (5) | −0.0030 (5) | 0.0020 (5) |
C5 | 0.0194 (6) | 0.0170 (6) | 0.0189 (6) | 0.0000 (5) | 0.0006 (5) | −0.0015 (5) |
C6 | 0.0184 (6) | 0.0179 (6) | 0.0191 (6) | −0.0002 (5) | −0.0007 (5) | −0.0023 (5) |
C7 | 0.0196 (6) | 0.0202 (6) | 0.0191 (6) | −0.0019 (5) | −0.0011 (5) | −0.0013 (5) |
C8 | 0.0213 (7) | 0.0235 (7) | 0.0233 (7) | −0.0022 (5) | −0.0039 (5) | 0.0011 (5) |
C9 | 0.0242 (7) | 0.0228 (7) | 0.0235 (7) | −0.0012 (5) | −0.0045 (5) | 0.0037 (5) |
C10 | 0.0225 (7) | 0.0206 (6) | 0.0218 (7) | −0.0029 (5) | 0.0017 (5) | −0.0002 (5) |
C11 | 0.0186 (6) | 0.0295 (7) | 0.0257 (7) | −0.0041 (5) | −0.0039 (5) | 0.0031 (6) |
C12 | 0.0215 (6) | 0.0262 (7) | 0.0216 (7) | −0.0010 (5) | −0.0032 (5) | 0.0035 (5) |
C13 | 0.0189 (6) | 0.0206 (6) | 0.0205 (6) | 0.0000 (5) | −0.0012 (5) | −0.0014 (5) |
C14 | 0.0334 (8) | 0.0311 (8) | 0.0297 (8) | −0.0064 (6) | 0.0015 (6) | 0.0108 (6) |
O1—C6 | 1.2367 (16) | C4—C5 | 1.3840 (18) |
O2—C13 | 1.3205 (16) | C4—H4A | 0.9500 |
O2—H1O2 | 0.98 (2) | C5—C6 | 1.5103 (18) |
O3—C13 | 1.2241 (16) | C7—C8 | 1.3872 (18) |
O4—C10 | 1.3619 (16) | C7—C12 | 1.3976 (18) |
O4—C14 | 1.4242 (17) | C7—C13 | 1.4860 (18) |
N1—C3 | 1.3347 (18) | C8—C9 | 1.3931 (19) |
N1—C2 | 1.3355 (18) | C8—H8A | 0.9500 |
N2—C6 | 1.3294 (17) | C9—C10 | 1.3897 (19) |
N2—H1N2 | 0.927 (19) | C9—H9A | 0.9500 |
N2—H2N2 | 0.92 (2) | C10—C11 | 1.3937 (19) |
C1—C2 | 1.3826 (19) | C11—C12 | 1.3732 (19) |
C1—C5 | 1.3845 (18) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C14—H14A | 0.9800 |
C3—C4 | 1.3867 (19) | C14—H14B | 0.9800 |
C3—H3A | 0.9500 | C14—H14C | 0.9800 |
C13—O2—H1O2 | 110.4 (13) | C12—C7—C13 | 119.11 (12) |
C10—O4—C14 | 117.81 (11) | C7—C8—C9 | 121.35 (12) |
C3—N1—C2 | 117.38 (12) | C7—C8—H8A | 119.3 |
C6—N2—H1N2 | 116.8 (11) | C9—C8—H8A | 119.3 |
C6—N2—H2N2 | 120.7 (11) | C10—C9—C8 | 119.02 (12) |
H1N2—N2—H2N2 | 122.5 (15) | C10—C9—H9A | 120.5 |
C2—C1—C5 | 119.10 (12) | C8—C9—H9A | 120.5 |
C2—C1—H1A | 120.5 | O4—C10—C9 | 124.77 (12) |
C5—C1—H1A | 120.5 | O4—C10—C11 | 115.22 (12) |
N1—C2—C1 | 123.17 (13) | C9—C10—C11 | 120.01 (12) |
N1—C2—H2A | 118.4 | C12—C11—C10 | 120.33 (12) |
C1—C2—H2A | 118.4 | C12—C11—H11A | 119.8 |
N1—C3—C4 | 123.36 (12) | C10—C11—H11A | 119.8 |
N1—C3—H3A | 118.3 | C11—C12—C7 | 120.64 (12) |
C4—C3—H3A | 118.3 | C11—C12—H12A | 119.7 |
C5—C4—C3 | 118.75 (12) | C7—C12—H12A | 119.7 |
C5—C4—H4A | 120.6 | O3—C13—O2 | 122.65 (12) |
C3—C4—H4A | 120.6 | O3—C13—C7 | 122.93 (12) |
C4—C5—C1 | 118.23 (12) | O2—C13—C7 | 114.42 (11) |
C4—C5—C6 | 124.54 (11) | O4—C14—H14A | 109.5 |
C1—C5—C6 | 117.22 (11) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 122.56 (12) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.25 (11) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 119.19 (11) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.63 (12) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 122.25 (12) | ||
C3—N1—C2—C1 | −0.5 (2) | C7—C8—C9—C10 | 0.1 (2) |
C5—C1—C2—N1 | 0.3 (2) | C14—O4—C10—C9 | 3.2 (2) |
C2—N1—C3—C4 | 0.1 (2) | C14—O4—C10—C11 | −176.46 (12) |
N1—C3—C4—C5 | 0.5 (2) | C8—C9—C10—O4 | −178.35 (12) |
C3—C4—C5—C1 | −0.7 (2) | C8—C9—C10—C11 | 1.3 (2) |
C3—C4—C5—C6 | −179.96 (12) | O4—C10—C11—C12 | 178.52 (12) |
C2—C1—C5—C4 | 0.3 (2) | C9—C10—C11—C12 | −1.1 (2) |
C2—C1—C5—C6 | 179.65 (12) | C10—C11—C12—C7 | −0.3 (2) |
C4—C5—C6—O1 | −179.50 (13) | C8—C7—C12—C11 | 1.6 (2) |
C1—C5—C6—O1 | 1.20 (18) | C13—C7—C12—C11 | −178.08 (12) |
C4—C5—C6—N2 | 1.34 (19) | C8—C7—C13—O3 | 171.32 (13) |
C1—C5—C6—N2 | −177.97 (12) | C12—C7—C13—O3 | −9.0 (2) |
C12—C7—C8—C9 | −1.5 (2) | C8—C7—C13—O2 | −8.79 (19) |
C13—C7—C8—C9 | 178.21 (12) | C12—C7—C13—O2 | 170.93 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.929 (19) | 1.980 (19) | 2.8992 (18) | 170.3 (15) |
N2—H2N2···O3ii | 0.923 (18) | 2.066 (18) | 2.9655 (19) | 164.5 (16) |
O2—H1O2···N1 | 0.98 (2) | 1.68 (2) | 2.6583 (17) | 178.6 (17) |
C4—H4A···O3ii | 0.95 | 2.46 | 3.393 (2) | 166 |
C11—H11A···O1iii | 0.95 | 2.44 | 3.074 (2) | 124 |
C14—H14A···O4iv | 0.98 | 2.57 | 3.543 (2) | 170 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z; (iv) −x+1, y−1/2, −z+3/2. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.388 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.088 (5) Å | Cell parameters from 3029 reflections |
b = 5.2242 (12) Å | θ = 2.6–27.5° |
c = 25.033 (6) Å | µ = 0.10 mm−1 |
β = 92.308 (16)° | T = 143 K |
V = 2624.9 (11) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3236 independent reflections |
Radiation source: fine-focus sealed tube | 2362 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −26→26 |
Tmin = 0.523, Tmax = 0.746 | k = −6→6 |
14186 measured reflections | l = −33→33 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0752P)2 + 0.3732P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3236 reflections | Δρmax = 0.27 e Å−3 |
194 parameters | Δρmin = −0.24 e Å−3 |
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 | 1.00104 (5) | 1.24472 (19) | 0.54425 (4) | 0.0263 (3) | |
O2 | 0.76805 (6) | 0.2656 (2) | 0.65588 (4) | 0.0345 (3) | |
H1O2 | 0.7956 (11) | 0.394 (5) | 0.6366 (9) | 0.069 (7)* | |
O3 | 0.70578 (5) | 0.24350 (19) | 0.58014 (4) | 0.0272 (3) | |
O4 | 0.56198 (5) | −0.5874 (2) | 0.72035 (4) | 0.0298 (3) | |
N1 | 0.83838 (6) | 0.5976 (2) | 0.60185 (5) | 0.0270 (3) | |
N2 | 0.91602 (6) | 1.3348 (2) | 0.48566 (5) | 0.0241 (3) | |
H1N2 | 0.9394 (9) | 1.465 (3) | 0.4730 (7) | 0.037 (5)* | |
H2N2 | 0.8753 (10) | 1.295 (3) | 0.4684 (7) | 0.036 (5)* | |
C1 | 0.93735 (7) | 0.8392 (3) | 0.58907 (6) | 0.0257 (3) | |
H1A | 0.9829 | 0.8693 | 0.5988 | 0.031* | |
C2 | 0.90241 (8) | 0.6492 (3) | 0.61405 (6) | 0.0289 (3) | |
H2A | 0.9248 | 0.5507 | 0.6411 | 0.035* | |
C3 | 0.80782 (8) | 0.7366 (3) | 0.56326 (6) | 0.0283 (3) | |
H3A | 0.7626 | 0.6995 | 0.5538 | 0.034* | |
C4 | 0.83896 (7) | 0.9319 (3) | 0.53640 (6) | 0.0263 (3) | |
H4A | 0.8153 | 1.0274 | 0.5095 | 0.032* | |
C5 | 0.90544 (7) | 0.9858 (3) | 0.54955 (5) | 0.0210 (3) | |
C6 | 0.94448 (7) | 1.1993 (3) | 0.52529 (5) | 0.0208 (3) | |
C7 | 0.67701 (7) | −0.0207 (3) | 0.65336 (5) | 0.0236 (3) | |
C8 | 0.68727 (8) | −0.0783 (3) | 0.70733 (6) | 0.0317 (4) | |
H8A | 0.7204 | 0.0117 | 0.7279 | 0.038* | |
C9 | 0.64965 (8) | −0.2659 (3) | 0.73165 (6) | 0.0326 (4) | |
H9A | 0.6568 | −0.3031 | 0.7686 | 0.039* | |
C10 | 0.60158 (7) | −0.3979 (3) | 0.70130 (6) | 0.0247 (3) | |
C11 | 0.59008 (8) | −0.3390 (3) | 0.64770 (6) | 0.0289 (3) | |
H11A | 0.5566 | −0.4277 | 0.6272 | 0.035* | |
C12 | 0.62733 (7) | −0.1513 (3) | 0.62421 (6) | 0.0278 (3) | |
H12A | 0.6189 | −0.1107 | 0.5876 | 0.033* | |
C13 | 0.71733 (7) | 0.1745 (3) | 0.62627 (6) | 0.0245 (3) | |
C14 | 0.56935 (9) | −0.6496 (4) | 0.77560 (7) | 0.0428 (4) | |
H14A | 0.5408 | −0.7960 | 0.7834 | 0.064* | |
H14B | 0.5564 | −0.5022 | 0.7970 | 0.064* | |
H14C | 0.6159 | −0.6935 | 0.7844 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0213 (5) | 0.0276 (5) | 0.0293 (6) | −0.0050 (4) | −0.0080 (4) | 0.0042 (4) |
O2 | 0.0298 (6) | 0.0438 (7) | 0.0290 (6) | −0.0176 (5) | −0.0091 (5) | 0.0079 (5) |
O3 | 0.0230 (5) | 0.0318 (6) | 0.0265 (6) | −0.0023 (4) | −0.0049 (4) | 0.0048 (4) |
O4 | 0.0266 (6) | 0.0332 (6) | 0.0295 (6) | −0.0068 (5) | −0.0021 (4) | 0.0072 (5) |
N1 | 0.0266 (7) | 0.0276 (6) | 0.0265 (6) | −0.0045 (5) | −0.0007 (5) | 0.0020 (5) |
N2 | 0.0210 (6) | 0.0246 (6) | 0.0263 (7) | −0.0040 (5) | −0.0049 (5) | 0.0040 (5) |
C1 | 0.0210 (7) | 0.0294 (8) | 0.0264 (7) | −0.0018 (6) | −0.0043 (6) | 0.0030 (6) |
C2 | 0.0283 (8) | 0.0301 (8) | 0.0280 (8) | −0.0019 (6) | −0.0047 (6) | 0.0062 (6) |
C3 | 0.0201 (7) | 0.0317 (8) | 0.0328 (8) | −0.0037 (6) | −0.0025 (6) | 0.0028 (6) |
C4 | 0.0222 (7) | 0.0276 (7) | 0.0285 (7) | −0.0011 (6) | −0.0046 (6) | 0.0040 (6) |
C5 | 0.0208 (7) | 0.0202 (7) | 0.0219 (7) | 0.0002 (5) | −0.0008 (5) | −0.0018 (5) |
C6 | 0.0202 (7) | 0.0211 (7) | 0.0208 (7) | 0.0000 (5) | −0.0016 (5) | −0.0026 (5) |
C7 | 0.0187 (7) | 0.0266 (7) | 0.0252 (7) | −0.0014 (6) | −0.0021 (5) | 0.0011 (6) |
C8 | 0.0282 (8) | 0.0395 (9) | 0.0266 (8) | −0.0096 (7) | −0.0071 (6) | 0.0020 (7) |
C9 | 0.0291 (8) | 0.0445 (10) | 0.0238 (8) | −0.0096 (7) | −0.0047 (6) | 0.0063 (7) |
C10 | 0.0200 (7) | 0.0269 (7) | 0.0272 (7) | −0.0003 (6) | 0.0004 (5) | 0.0027 (6) |
C11 | 0.0257 (8) | 0.0333 (8) | 0.0271 (8) | −0.0073 (6) | −0.0060 (6) | 0.0002 (6) |
C12 | 0.0261 (8) | 0.0333 (8) | 0.0236 (7) | −0.0034 (6) | −0.0052 (6) | 0.0042 (6) |
C13 | 0.0196 (7) | 0.0273 (7) | 0.0264 (7) | 0.0004 (6) | −0.0037 (5) | 0.0004 (6) |
C14 | 0.0406 (10) | 0.0535 (11) | 0.0338 (9) | −0.0156 (9) | −0.0045 (7) | 0.0157 (8) |
O1—C6 | 1.2366 (17) | C4—C5 | 1.391 (2) |
O2—C13 | 1.3241 (17) | C4—H4A | 0.9500 |
O2—H1O2 | 1.01 (2) | C5—C6 | 1.5053 (19) |
O3—C13 | 1.2230 (17) | C7—C12 | 1.391 (2) |
O4—C10 | 1.3677 (17) | C7—C8 | 1.391 (2) |
O4—C14 | 1.4228 (19) | C7—C13 | 1.483 (2) |
N1—C2 | 1.3374 (19) | C8—C9 | 1.393 (2) |
N1—C3 | 1.3377 (19) | C8—H8A | 0.9500 |
N2—C6 | 1.3290 (18) | C9—C10 | 1.388 (2) |
N2—H1N2 | 0.891 (19) | C9—H9A | 0.9500 |
N2—H2N2 | 0.933 (19) | C10—C11 | 1.387 (2) |
C1—C2 | 1.380 (2) | C11—C12 | 1.379 (2) |
C1—C5 | 1.3875 (19) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C14—H14A | 0.9800 |
C3—C4 | 1.385 (2) | C14—H14B | 0.9800 |
C3—H3A | 0.9500 | C14—H14C | 0.9800 |
C13—O2—H1O2 | 113.5 (12) | C8—C7—C13 | 122.03 (13) |
C10—O4—C14 | 117.72 (12) | C7—C8—C9 | 120.99 (14) |
C2—N1—C3 | 117.69 (13) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 116.9 (11) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 124.8 (11) | C10—C9—C8 | 119.23 (14) |
H1N2—N2—H2N2 | 118.0 (16) | C10—C9—H9A | 120.4 |
C2—C1—C5 | 119.44 (14) | C8—C9—H9A | 120.4 |
C2—C1—H1A | 120.3 | O4—C10—C11 | 114.92 (13) |
C5—C1—H1A | 120.3 | O4—C10—C9 | 124.78 (13) |
N1—C2—C1 | 122.93 (14) | C11—C10—C9 | 120.30 (14) |
N1—C2—H2A | 118.5 | C12—C11—C10 | 119.88 (13) |
C1—C2—H2A | 118.5 | C12—C11—H11A | 120.1 |
N1—C3—C4 | 123.17 (13) | C10—C11—H11A | 120.1 |
N1—C3—H3A | 118.4 | C11—C12—C7 | 121.00 (13) |
C4—C3—H3A | 118.4 | C11—C12—H12A | 119.5 |
C3—C4—C5 | 118.84 (13) | C7—C12—H12A | 119.5 |
C3—C4—H4A | 120.6 | O3—C13—O2 | 122.35 (13) |
C5—C4—H4A | 120.6 | O3—C13—C7 | 123.23 (13) |
C1—C5—C4 | 117.92 (13) | O2—C13—C7 | 114.41 (12) |
C1—C5—C6 | 117.62 (12) | O4—C14—H14A | 109.5 |
C4—C5—C6 | 124.42 (12) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 123.06 (13) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.21 (12) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.70 (12) | H14A—C14—H14C | 109.5 |
C12—C7—C8 | 118.57 (13) | H14B—C14—H14C | 109.5 |
C12—C7—C13 | 119.40 (13) | ||
C3—N1—C2—C1 | 0.7 (2) | C7—C8—C9—C10 | 0.4 (2) |
C5—C1—C2—N1 | 0.2 (2) | C14—O4—C10—C11 | −177.43 (15) |
C2—N1—C3—C4 | −1.1 (2) | C14—O4—C10—C9 | 1.7 (2) |
N1—C3—C4—C5 | 0.7 (2) | C8—C9—C10—O4 | 179.36 (14) |
C2—C1—C5—C4 | −0.6 (2) | C8—C9—C10—C11 | −1.6 (2) |
C2—C1—C5—C6 | 177.05 (13) | O4—C10—C11—C12 | −179.77 (14) |
C3—C4—C5—C1 | 0.2 (2) | C9—C10—C11—C12 | 1.1 (2) |
C3—C4—C5—C6 | −177.30 (13) | C10—C11—C12—C7 | 0.6 (2) |
C1—C5—C6—O1 | −4.99 (19) | C8—C7—C12—C11 | −1.7 (2) |
C4—C5—C6—O1 | 172.55 (14) | C13—C7—C12—C11 | 178.21 (14) |
C1—C5—C6—N2 | 176.92 (13) | C12—C7—C13—O3 | 6.2 (2) |
C4—C5—C6—N2 | −5.5 (2) | C8—C7—C13—O3 | −173.82 (15) |
C12—C7—C8—C9 | 1.2 (2) | C12—C7—C13—O2 | −172.54 (13) |
C13—C7—C8—C9 | −178.73 (14) | C8—C7—C13—O2 | 7.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···N1 | 1.01 (2) | 1.64 (2) | 2.6434 (17) | 177 (2) |
N2—H1N2···O1i | 0.892 (17) | 1.990 (17) | 2.8744 (17) | 171.1 (16) |
N2—H2N2···O3ii | 0.933 (19) | 2.011 (19) | 2.9330 (17) | 169.6 (15) |
C4—H4A···O3ii | 0.95 | 2.53 | 3.429 (2) | 157 |
C11—H11A···O1iii | 0.95 | 2.51 | 3.127 (2) | 123 |
C14—H14A···O4iv | 0.98 | 2.56 | 3.496 (2) | 159 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z; (iv) −x+1, y−1/2, −z+3/2. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.389 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.084 (2) Å | Cell parameters from 4895 reflections |
b = 5.2206 (6) Å | θ = 2.6–28.8° |
c = 25.040 (3) Å | µ = 0.10 mm−1 |
β = 92.375 (8)° | T = 150 K |
V = 2623.2 (5) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3520 independent reflections |
Radiation source: fine-focus sealed tube | 2765 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 29.2°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −27→27 |
Tmin = 0.915, Tmax = 0.969 | k = −7→7 |
21034 measured reflections | l = −34→34 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0672P)2 + 0.9974P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3520 reflections | Δρmax = 0.31 e Å−3 |
194 parameters | Δρmin = −0.19 e Å−3 |
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 | 1.00105 (4) | 1.24515 (16) | 0.54426 (3) | 0.0259 (2) | |
O2 | 0.76799 (5) | 0.26540 (19) | 0.65585 (4) | 0.0342 (3) | |
H1O2 | 0.7940 (10) | 0.386 (4) | 0.6360 (8) | 0.073 (6)* | |
O3 | 0.70571 (4) | 0.24354 (17) | 0.58014 (3) | 0.0268 (2) | |
O4 | 0.56200 (4) | −0.58732 (18) | 0.72039 (3) | 0.0299 (2) | |
N1 | 0.83830 (5) | 0.5979 (2) | 0.60184 (4) | 0.0265 (2) | |
N2 | 0.91604 (5) | 1.3347 (2) | 0.48565 (4) | 0.0236 (2) | |
H1N2 | 0.9399 (8) | 1.469 (3) | 0.4731 (6) | 0.037 (4)* | |
H2N2 | 0.8761 (8) | 1.297 (3) | 0.4693 (6) | 0.029 (4)* | |
C1 | 0.93755 (6) | 0.8393 (2) | 0.58907 (5) | 0.0249 (3) | |
H1A | 0.9831 | 0.8695 | 0.5988 | 0.030* | |
C2 | 0.90245 (6) | 0.6492 (3) | 0.61392 (5) | 0.0283 (3) | |
H2A | 0.9249 | 0.5500 | 0.6409 | 0.034* | |
C3 | 0.80776 (6) | 0.7365 (2) | 0.56324 (5) | 0.0281 (3) | |
H3A | 0.7625 | 0.6993 | 0.5537 | 0.034* | |
C4 | 0.83903 (6) | 0.9323 (2) | 0.53635 (5) | 0.0259 (3) | |
H4A | 0.8155 | 1.0279 | 0.5094 | 0.031* | |
C5 | 0.90536 (6) | 0.9855 (2) | 0.54962 (4) | 0.0205 (2) | |
C6 | 0.94449 (6) | 1.1995 (2) | 0.52532 (4) | 0.0202 (2) | |
C7 | 0.67698 (6) | −0.0203 (2) | 0.65340 (5) | 0.0230 (2) | |
C8 | 0.68741 (6) | −0.0781 (3) | 0.70733 (5) | 0.0309 (3) | |
H8A | 0.7207 | 0.0116 | 0.7279 | 0.037* | |
C9 | 0.64976 (7) | −0.2654 (3) | 0.73162 (5) | 0.0321 (3) | |
H9A | 0.6570 | −0.3025 | 0.7686 | 0.039* | |
C10 | 0.60149 (6) | −0.3978 (2) | 0.70132 (5) | 0.0245 (3) | |
C11 | 0.59007 (6) | −0.3390 (3) | 0.64776 (5) | 0.0285 (3) | |
H11A | 0.5566 | −0.4280 | 0.6273 | 0.034* | |
C12 | 0.62735 (6) | −0.1511 (3) | 0.62411 (5) | 0.0272 (3) | |
H12A | 0.6190 | −0.1107 | 0.5875 | 0.033* | |
C13 | 0.71729 (6) | 0.1749 (2) | 0.62628 (5) | 0.0236 (3) | |
C14 | 0.56939 (8) | −0.6487 (3) | 0.77558 (6) | 0.0431 (4) | |
H14A | 0.5401 | −0.7927 | 0.7836 | 0.065* | |
H14B | 0.5573 | −0.4997 | 0.7969 | 0.065* | |
H14C | 0.6158 | −0.6961 | 0.7843 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0216 (4) | 0.0273 (5) | 0.0284 (5) | −0.0056 (3) | −0.0051 (3) | 0.0043 (3) |
O2 | 0.0295 (5) | 0.0440 (6) | 0.0286 (5) | −0.0172 (4) | −0.0069 (4) | 0.0092 (4) |
O3 | 0.0225 (4) | 0.0322 (5) | 0.0255 (5) | −0.0019 (3) | −0.0021 (3) | 0.0050 (3) |
O4 | 0.0273 (5) | 0.0335 (5) | 0.0288 (5) | −0.0079 (4) | 0.0006 (4) | 0.0073 (4) |
N1 | 0.0259 (5) | 0.0269 (5) | 0.0270 (5) | −0.0052 (4) | 0.0023 (4) | 0.0023 (4) |
N2 | 0.0216 (5) | 0.0240 (5) | 0.0250 (5) | −0.0040 (4) | −0.0032 (4) | 0.0040 (4) |
C1 | 0.0204 (5) | 0.0287 (6) | 0.0253 (6) | −0.0024 (5) | −0.0026 (4) | 0.0029 (5) |
C2 | 0.0275 (6) | 0.0296 (6) | 0.0274 (6) | −0.0025 (5) | −0.0030 (5) | 0.0078 (5) |
C3 | 0.0204 (6) | 0.0312 (7) | 0.0328 (7) | −0.0041 (5) | 0.0014 (5) | 0.0034 (5) |
C4 | 0.0211 (6) | 0.0276 (6) | 0.0285 (6) | −0.0019 (5) | −0.0023 (5) | 0.0042 (5) |
C5 | 0.0207 (5) | 0.0200 (5) | 0.0208 (5) | −0.0009 (4) | 0.0015 (4) | −0.0012 (4) |
C6 | 0.0194 (5) | 0.0202 (5) | 0.0210 (5) | −0.0006 (4) | 0.0008 (4) | −0.0023 (4) |
C7 | 0.0188 (5) | 0.0262 (6) | 0.0240 (6) | −0.0018 (4) | 0.0005 (4) | 0.0013 (5) |
C8 | 0.0274 (6) | 0.0391 (7) | 0.0257 (6) | −0.0108 (5) | −0.0046 (5) | 0.0020 (5) |
C9 | 0.0302 (7) | 0.0436 (8) | 0.0223 (6) | −0.0093 (6) | −0.0022 (5) | 0.0058 (5) |
C10 | 0.0202 (5) | 0.0263 (6) | 0.0273 (6) | −0.0016 (4) | 0.0024 (4) | 0.0030 (5) |
C11 | 0.0254 (6) | 0.0328 (7) | 0.0269 (6) | −0.0080 (5) | −0.0028 (5) | 0.0012 (5) |
C12 | 0.0249 (6) | 0.0338 (7) | 0.0226 (6) | −0.0051 (5) | −0.0031 (5) | 0.0041 (5) |
C13 | 0.0193 (5) | 0.0268 (6) | 0.0247 (6) | −0.0005 (5) | −0.0008 (4) | 0.0014 (5) |
C14 | 0.0422 (8) | 0.0549 (9) | 0.0320 (7) | −0.0171 (7) | −0.0017 (6) | 0.0162 (7) |
O1—C6 | 1.2358 (14) | C4—C5 | 1.3876 (16) |
O2—C13 | 1.3214 (14) | C4—H4A | 0.9500 |
O2—H1O2 | 0.97 (2) | C5—C6 | 1.5084 (16) |
O3—C13 | 1.2229 (14) | C7—C8 | 1.3911 (17) |
O4—C10 | 1.3664 (14) | C7—C12 | 1.3917 (16) |
O4—C14 | 1.4203 (16) | C7—C13 | 1.4833 (16) |
N1—C3 | 1.3359 (16) | C8—C9 | 1.3916 (18) |
N1—C2 | 1.3383 (16) | C8—H8A | 0.9500 |
N2—C6 | 1.3284 (15) | C9—C10 | 1.3901 (17) |
N2—H1N2 | 0.910 (17) | C9—H9A | 0.9500 |
N2—H2N2 | 0.906 (16) | C10—C11 | 1.3856 (17) |
C1—C2 | 1.3803 (18) | C11—C12 | 1.3822 (18) |
C1—C5 | 1.3870 (16) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C14—H14A | 0.9800 |
C3—C4 | 1.3883 (17) | C14—H14B | 0.9800 |
C3—H3A | 0.9500 | C14—H14C | 0.9800 |
C13—O2—H1O2 | 111.4 (12) | C12—C7—C13 | 119.24 (10) |
C10—O4—C14 | 117.69 (10) | C7—C8—C9 | 120.94 (12) |
C3—N1—C2 | 117.66 (11) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 116.6 (10) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 124.7 (10) | C10—C9—C8 | 119.35 (12) |
H1N2—N2—H2N2 | 118.6 (14) | C10—C9—H9A | 120.3 |
C2—C1—C5 | 119.02 (11) | C8—C9—H9A | 120.3 |
C2—C1—H1A | 120.5 | O4—C10—C11 | 115.06 (11) |
C5—C1—H1A | 120.5 | O4—C10—C9 | 124.82 (11) |
N1—C2—C1 | 123.14 (12) | C11—C10—C9 | 120.12 (11) |
N1—C2—H2A | 118.4 | C12—C11—C10 | 120.07 (11) |
C1—C2—H2A | 118.4 | C12—C11—H11A | 120.0 |
N1—C3—C4 | 123.10 (11) | C10—C11—H11A | 120.0 |
N1—C3—H3A | 118.4 | C11—C12—C7 | 120.76 (11) |
C4—C3—H3A | 118.4 | C11—C12—H12A | 119.6 |
C5—C4—C3 | 118.72 (11) | C7—C12—H12A | 119.6 |
C5—C4—H4A | 120.6 | O3—C13—O2 | 122.45 (11) |
C3—C4—H4A | 120.6 | O3—C13—C7 | 123.22 (11) |
C1—C5—C4 | 118.34 (11) | O2—C13—C7 | 114.31 (10) |
C1—C5—C6 | 117.36 (10) | O4—C14—H14A | 109.5 |
C4—C5—C6 | 124.26 (10) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 122.99 (11) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.30 (10) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.68 (10) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.74 (11) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 122.02 (11) | ||
C3—N1—C2—C1 | 1.0 (2) | C7—C8—C9—C10 | 0.6 (2) |
C5—C1—C2—N1 | 0.0 (2) | C14—O4—C10—C11 | −177.37 (13) |
C2—N1—C3—C4 | −1.41 (19) | C14—O4—C10—C9 | 1.93 (19) |
N1—C3—C4—C5 | 0.74 (19) | C8—C9—C10—O4 | 179.22 (12) |
C2—C1—C5—C4 | −0.67 (18) | C8—C9—C10—C11 | −1.5 (2) |
C2—C1—C5—C6 | 177.14 (11) | O4—C10—C11—C12 | −179.69 (12) |
C3—C4—C5—C1 | 0.33 (18) | C9—C10—C11—C12 | 1.0 (2) |
C3—C4—C5—C6 | −177.31 (11) | C10—C11—C12—C7 | 0.5 (2) |
C1—C5—C6—O1 | −5.10 (16) | C8—C7—C12—C11 | −1.4 (2) |
C4—C5—C6—O1 | 172.57 (12) | C13—C7—C12—C11 | 178.23 (12) |
C1—C5—C6—N2 | 176.75 (11) | C8—C7—C13—O3 | −174.03 (12) |
C4—C5—C6—N2 | −5.58 (17) | C12—C7—C13—O3 | 6.31 (19) |
C12—C7—C8—C9 | 0.9 (2) | C8—C7—C13—O2 | 7.33 (18) |
C13—C7—C8—C9 | −178.77 (12) | C12—C7—C13—O2 | −172.33 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···N1 | 0.97 (2) | 1.68 (2) | 2.6447 (15) | 179 (2) |
N2—H1N2···O1i | 0.912 (16) | 1.966 (16) | 2.8720 (14) | 171.8 (14) |
N2—H2N2···O3ii | 0.907 (16) | 2.035 (16) | 2.9301 (13) | 168.8 (14) |
C4—H4A···O3ii | 0.95 | 2.53 | 3.4262 (15) | 158 |
C11—H11A···O1iii | 0.95 | 2.51 | 3.1256 (15) | 123 |
C14—H14A···O4iv | 0.98 | 2.56 | 3.4985 (19) | 160 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z; (iv) −x+1, y−1/2, −z+3/2. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.381 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.126 (5) Å | Cell parameters from 2724 reflections |
b = 5.2212 (12) Å | θ = 2.5–25.7° |
c = 25.134 (6) Å | µ = 0.10 mm−1 |
β = 92.401 (16)° | T = 200 K |
V = 2638.8 (11) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3259 independent reflections |
Radiation source: fine-focus sealed tube | 2204 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −26→26 |
Tmin = 0.660, Tmax = 0.969 | k = −6→6 |
14445 measured reflections | l = −33→33 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0834P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3259 reflections | Δρmax = 0.27 e Å−3 |
194 parameters | Δρmin = −0.21 e Å−3 |
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 | 1.00083 (5) | 1.2458 (2) | 0.54443 (4) | 0.0349 (3) | |
O2 | 0.76788 (6) | 0.2659 (2) | 0.65543 (5) | 0.0454 (4) | |
H1O2 | 0.7929 (11) | 0.388 (4) | 0.6357 (8) | 0.072 (7)* | |
O3 | 0.70561 (5) | 0.2434 (2) | 0.58023 (4) | 0.0362 (3) | |
O4 | 0.56217 (6) | −0.5834 (2) | 0.72070 (4) | 0.0401 (3) | |
N1 | 0.83840 (7) | 0.5992 (3) | 0.60167 (5) | 0.0354 (3) | |
N2 | 0.91625 (7) | 1.3338 (3) | 0.48579 (5) | 0.0318 (3) | |
H1N2 | 0.9407 (9) | 1.468 (3) | 0.4737 (6) | 0.040 (5)* | |
H2N2 | 0.8760 (10) | 1.299 (3) | 0.4698 (7) | 0.042 (5)* | |
C1 | 0.93706 (8) | 0.8404 (3) | 0.58908 (6) | 0.0331 (4) | |
H1A | 0.9825 | 0.8703 | 0.5988 | 0.040* | |
C2 | 0.90219 (8) | 0.6512 (3) | 0.61395 (6) | 0.0379 (4) | |
H2A | 0.9245 | 0.5533 | 0.6411 | 0.045* | |
C3 | 0.80810 (8) | 0.7371 (3) | 0.56329 (7) | 0.0371 (4) | |
H3A | 0.7629 | 0.7002 | 0.5539 | 0.044* | |
C4 | 0.83928 (7) | 0.9321 (3) | 0.53640 (6) | 0.0346 (4) | |
H4A | 0.8158 | 1.0267 | 0.5093 | 0.042* | |
C5 | 0.90531 (7) | 0.9866 (3) | 0.54978 (5) | 0.0271 (3) | |
C6 | 0.94444 (7) | 1.1996 (3) | 0.52556 (6) | 0.0269 (3) | |
C7 | 0.67704 (7) | −0.0196 (3) | 0.65336 (6) | 0.0305 (3) | |
C8 | 0.68753 (8) | −0.0766 (3) | 0.70678 (6) | 0.0406 (4) | |
H8A | 0.7209 | 0.0131 | 0.7271 | 0.049* | |
C9 | 0.65007 (9) | −0.2630 (3) | 0.73122 (6) | 0.0422 (4) | |
H9A | 0.6575 | −0.2995 | 0.7680 | 0.051* | |
C10 | 0.60180 (7) | −0.3951 (3) | 0.70145 (6) | 0.0331 (4) | |
C11 | 0.59033 (8) | −0.3371 (3) | 0.64818 (6) | 0.0383 (4) | |
H11A | 0.5568 | −0.4262 | 0.6279 | 0.046* | |
C12 | 0.62742 (8) | −0.1501 (3) | 0.62442 (6) | 0.0365 (4) | |
H12A | 0.6189 | −0.1103 | 0.5879 | 0.044* | |
C13 | 0.71712 (7) | 0.1748 (3) | 0.62616 (6) | 0.0317 (4) | |
C14 | 0.56967 (10) | −0.6453 (4) | 0.77556 (7) | 0.0577 (6) | |
H14A | 0.5403 | −0.7887 | 0.7836 | 0.087* | |
H14B | 0.5579 | −0.4962 | 0.7969 | 0.087* | |
H14C | 0.6159 | −0.6937 | 0.7841 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0280 (6) | 0.0367 (6) | 0.0393 (6) | −0.0082 (5) | −0.0089 (5) | 0.0063 (5) |
O2 | 0.0391 (7) | 0.0578 (8) | 0.0381 (7) | −0.0232 (6) | −0.0116 (5) | 0.0126 (6) |
O3 | 0.0301 (6) | 0.0439 (7) | 0.0342 (6) | −0.0032 (5) | −0.0058 (5) | 0.0066 (5) |
O4 | 0.0353 (6) | 0.0448 (7) | 0.0400 (6) | −0.0104 (5) | −0.0010 (5) | 0.0095 (5) |
N1 | 0.0337 (8) | 0.0361 (7) | 0.0364 (7) | −0.0063 (6) | 0.0015 (6) | 0.0032 (6) |
N2 | 0.0280 (7) | 0.0325 (7) | 0.0341 (7) | −0.0056 (6) | −0.0063 (6) | 0.0057 (6) |
C1 | 0.0268 (8) | 0.0376 (8) | 0.0344 (8) | −0.0035 (7) | −0.0049 (6) | 0.0052 (7) |
C2 | 0.0355 (9) | 0.0405 (9) | 0.0371 (9) | −0.0027 (7) | −0.0061 (7) | 0.0091 (7) |
C3 | 0.0260 (8) | 0.0410 (9) | 0.0438 (10) | −0.0061 (7) | −0.0016 (7) | 0.0047 (7) |
C4 | 0.0265 (8) | 0.0362 (8) | 0.0407 (9) | −0.0019 (6) | −0.0054 (6) | 0.0069 (7) |
C5 | 0.0257 (8) | 0.0270 (7) | 0.0286 (7) | −0.0004 (6) | −0.0002 (6) | −0.0011 (6) |
C6 | 0.0242 (7) | 0.0279 (7) | 0.0286 (7) | −0.0007 (6) | −0.0008 (6) | −0.0024 (6) |
C7 | 0.0247 (8) | 0.0357 (8) | 0.0309 (8) | −0.0013 (6) | −0.0019 (6) | 0.0010 (6) |
C8 | 0.0345 (9) | 0.0523 (10) | 0.0343 (9) | −0.0128 (8) | −0.0084 (7) | 0.0034 (7) |
C9 | 0.0388 (10) | 0.0574 (11) | 0.0300 (9) | −0.0122 (8) | −0.0051 (7) | 0.0072 (7) |
C10 | 0.0278 (8) | 0.0345 (8) | 0.0368 (8) | −0.0014 (7) | 0.0017 (6) | 0.0035 (6) |
C11 | 0.0333 (9) | 0.0437 (9) | 0.0372 (9) | −0.0102 (7) | −0.0059 (7) | 0.0008 (7) |
C12 | 0.0323 (9) | 0.0452 (9) | 0.0312 (8) | −0.0067 (7) | −0.0066 (6) | 0.0057 (7) |
C13 | 0.0246 (8) | 0.0367 (8) | 0.0334 (8) | −0.0004 (6) | −0.0039 (6) | 0.0014 (7) |
C14 | 0.0573 (13) | 0.0724 (14) | 0.0431 (10) | −0.0201 (11) | −0.0030 (9) | 0.0201 (10) |
O1—C6 | 1.2355 (17) | C4—C5 | 1.386 (2) |
O2—C13 | 1.3222 (18) | C4—H4A | 0.9500 |
O2—H1O2 | 0.96 (2) | C5—C6 | 1.506 (2) |
O3—C13 | 1.2218 (17) | C7—C8 | 1.383 (2) |
O4—C10 | 1.3672 (18) | C7—C12 | 1.389 (2) |
O4—C14 | 1.418 (2) | C7—C13 | 1.481 (2) |
N1—C3 | 1.331 (2) | C8—C9 | 1.390 (2) |
N1—C2 | 1.336 (2) | C8—H8A | 0.9500 |
N2—C6 | 1.3284 (19) | C9—C10 | 1.385 (2) |
N2—H1N2 | 0.917 (18) | C9—H9A | 0.9500 |
N2—H2N2 | 0.91 (2) | C10—C11 | 1.382 (2) |
C1—C2 | 1.377 (2) | C11—C12 | 1.380 (2) |
C1—C5 | 1.384 (2) | C11—H11A | 0.9500 |
C1—H1A | 0.9500 | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C14—H14A | 0.9800 |
C3—C4 | 1.386 (2) | C14—H14B | 0.9800 |
C3—H3A | 0.9500 | C14—H14C | 0.9800 |
C13—O2—H1O2 | 111.1 (12) | C12—C7—C13 | 119.21 (13) |
C10—O4—C14 | 117.90 (13) | C7—C8—C9 | 121.08 (15) |
C3—N1—C2 | 117.64 (14) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 115.9 (10) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 124.8 (12) | C10—C9—C8 | 119.42 (15) |
H1N2—N2—H2N2 | 119.3 (16) | C10—C9—H9A | 120.3 |
C2—C1—C5 | 119.40 (15) | C8—C9—H9A | 120.3 |
C2—C1—H1A | 120.3 | O4—C10—C11 | 115.08 (14) |
C5—C1—H1A | 120.3 | O4—C10—C9 | 124.98 (14) |
N1—C2—C1 | 122.99 (15) | C11—C10—C9 | 119.93 (14) |
N1—C2—H2A | 118.5 | C12—C11—C10 | 120.17 (14) |
C1—C2—H2A | 118.5 | C12—C11—H11A | 119.9 |
N1—C3—C4 | 123.20 (15) | C10—C11—H11A | 119.9 |
N1—C3—H3A | 118.4 | C11—C12—C7 | 120.70 (14) |
C4—C3—H3A | 118.4 | C11—C12—H12A | 119.6 |
C3—C4—C5 | 118.76 (14) | C7—C12—H12A | 119.6 |
C3—C4—H4A | 120.6 | O3—C13—O2 | 122.12 (14) |
C5—C4—H4A | 120.6 | O3—C13—C7 | 123.49 (13) |
C1—C5—C4 | 117.99 (14) | O2—C13—C7 | 114.38 (13) |
C1—C5—C6 | 117.54 (13) | O4—C14—H14A | 109.5 |
C4—C5—C6 | 124.45 (13) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 122.84 (14) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.47 (13) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.67 (13) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.67 (14) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 122.12 (14) | ||
C3—N1—C2—C1 | 0.5 (3) | C7—C8—C9—C10 | 0.5 (3) |
C5—C1—C2—N1 | 0.5 (3) | C14—O4—C10—C11 | −177.65 (16) |
C2—N1—C3—C4 | −0.9 (2) | C14—O4—C10—C9 | 1.5 (2) |
N1—C3—C4—C5 | 0.3 (2) | C8—C9—C10—O4 | 179.50 (16) |
C2—C1—C5—C4 | −1.1 (2) | C8—C9—C10—C11 | −1.3 (3) |
C2—C1—C5—C6 | 177.09 (14) | O4—C10—C11—C12 | −179.96 (15) |
C3—C4—C5—C1 | 0.8 (2) | C9—C10—C11—C12 | 0.8 (3) |
C3—C4—C5—C6 | −177.33 (14) | C10—C11—C12—C7 | 0.6 (3) |
C1—C5—C6—O1 | −5.3 (2) | C8—C7—C12—C11 | −1.5 (3) |
C4—C5—C6—O1 | 172.84 (15) | C13—C7—C12—C11 | 178.29 (15) |
C1—C5—C6—N2 | 176.45 (14) | C8—C7—C13—O3 | −174.03 (16) |
C4—C5—C6—N2 | −5.5 (2) | C12—C7—C13—O3 | 6.2 (2) |
C12—C7—C8—C9 | 0.9 (3) | C8—C7—C13—O2 | 7.3 (2) |
C13—C7—C8—C9 | −178.83 (15) | C12—C7—C13—O2 | −172.44 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···N1 | 0.96 (2) | 1.69 (2) | 2.651 (2) | 179 (2) |
N2—H1N2···O1i | 0.915 (17) | 1.967 (17) | 2.879 (2) | 173.4 (14) |
N2—H2N2···O3ii | 0.908 (19) | 2.047 (19) | 2.9411 (18) | 168.2 (16) |
C4—H4A···O3ii | 0.95 | 2.54 | 3.439 (2) | 158 |
C11—H11A···O1iii | 0.95 | 2.52 | 3.143 (2) | 123 |
C14—H14A···O4iv | 0.98 | 2.57 | 3.508 (2) | 160 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z; (iv) −x+1, y−1/2, −z+3/2. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.374 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.161 (4) Å | Cell parameters from 2401 reflections |
b = 5.2180 (11) Å | θ = 2.5–25.6° |
c = 25.234 (5) Å | µ = 0.10 mm−1 |
β = 92.559 (14)° | T = 250 K |
V = 2652.0 (9) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker APEX Duo CCD area detector diffractometer | 3225 independent reflections |
Radiation source: fine-focus sealed tube | 2102 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 28.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −26→24 |
Tmin = 0.836, Tmax = 0.969 | k = −6→6 |
14256 measured reflections | l = −33→33 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0819P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3225 reflections | Δρmax = 0.23 e Å−3 |
194 parameters | Δρmin = −0.18 e Å−3 |
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 | 1.00048 (5) | 1.2464 (2) | 0.54466 (4) | 0.0426 (3) | |
O2 | 0.76769 (6) | 0.2665 (3) | 0.65495 (5) | 0.0551 (4) | |
H1O2 | 0.7959 (12) | 0.379 (5) | 0.6360 (9) | 0.095 (8)* | |
O3 | 0.70544 (6) | 0.2435 (2) | 0.58019 (4) | 0.0443 (3) | |
O4 | 0.56250 (6) | −0.5795 (2) | 0.72084 (5) | 0.0502 (3) | |
N1 | 0.83831 (7) | 0.6007 (3) | 0.60153 (5) | 0.0434 (4) | |
N2 | 0.91633 (7) | 1.3329 (3) | 0.48603 (5) | 0.0385 (3) | |
H1N2 | 0.9405 (9) | 1.460 (3) | 0.4738 (6) | 0.044 (5)* | |
H2N2 | 0.8752 (10) | 1.303 (4) | 0.4707 (7) | 0.048 (5)* | |
C1 | 0.93672 (8) | 0.8421 (3) | 0.58919 (6) | 0.0411 (4) | |
H1A | 0.9815 | 0.8723 | 0.5991 | 0.049* | |
C2 | 0.90180 (9) | 0.6525 (4) | 0.61371 (7) | 0.0463 (4) | |
H2A | 0.9239 | 0.5548 | 0.6404 | 0.056* | |
C3 | 0.80829 (9) | 0.7381 (3) | 0.56308 (7) | 0.0462 (4) | |
H3A | 0.7637 | 0.7014 | 0.5535 | 0.055* | |
C4 | 0.83969 (8) | 0.9331 (3) | 0.53643 (7) | 0.0421 (4) | |
H4A | 0.8166 | 1.0267 | 0.5096 | 0.050* | |
C5 | 0.90527 (7) | 0.9872 (3) | 0.54988 (5) | 0.0324 (3) | |
C6 | 0.94449 (7) | 1.2004 (3) | 0.52571 (6) | 0.0323 (3) | |
C7 | 0.67698 (7) | −0.0184 (3) | 0.65318 (6) | 0.0367 (4) | |
C8 | 0.68781 (9) | −0.0748 (4) | 0.70636 (7) | 0.0494 (5) | |
H8A | 0.7210 | 0.0137 | 0.7263 | 0.059* | |
C9 | 0.65040 (9) | −0.2600 (4) | 0.73087 (7) | 0.0506 (5) | |
H9A | 0.6579 | −0.2957 | 0.7672 | 0.061* | |
C10 | 0.60205 (8) | −0.3914 (3) | 0.70139 (6) | 0.0396 (4) | |
C11 | 0.59047 (9) | −0.3342 (4) | 0.64857 (7) | 0.0463 (4) | |
H11A | 0.5572 | −0.4224 | 0.6286 | 0.056* | |
C12 | 0.62732 (8) | −0.1484 (4) | 0.62478 (6) | 0.0451 (4) | |
H12A | 0.6186 | −0.1094 | 0.5888 | 0.054* | |
C13 | 0.71710 (8) | 0.1754 (3) | 0.62590 (6) | 0.0375 (4) | |
C14 | 0.57026 (11) | −0.6410 (5) | 0.77532 (8) | 0.0715 (7) | |
H14A | 0.5428 | −0.7880 | 0.7830 | 0.107* | |
H14B | 0.5568 | −0.4959 | 0.7963 | 0.107* | |
H14C | 0.6164 | −0.6814 | 0.7840 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0362 (6) | 0.0430 (7) | 0.0475 (7) | −0.0101 (5) | −0.0105 (5) | 0.0084 (5) |
O2 | 0.0490 (8) | 0.0692 (9) | 0.0458 (7) | −0.0268 (7) | −0.0112 (6) | 0.0140 (6) |
O3 | 0.0393 (7) | 0.0519 (7) | 0.0409 (7) | −0.0039 (5) | −0.0050 (5) | 0.0097 (5) |
O4 | 0.0466 (7) | 0.0538 (7) | 0.0500 (7) | −0.0136 (6) | 0.0006 (5) | 0.0110 (6) |
N1 | 0.0426 (8) | 0.0422 (8) | 0.0456 (8) | −0.0071 (6) | 0.0025 (6) | 0.0032 (6) |
N2 | 0.0351 (8) | 0.0382 (8) | 0.0414 (8) | −0.0060 (6) | −0.0066 (6) | 0.0068 (6) |
C1 | 0.0355 (9) | 0.0449 (9) | 0.0424 (9) | −0.0047 (7) | −0.0055 (7) | 0.0070 (7) |
C2 | 0.0455 (10) | 0.0477 (10) | 0.0448 (9) | −0.0040 (8) | −0.0063 (7) | 0.0122 (8) |
C3 | 0.0329 (9) | 0.0491 (10) | 0.0565 (11) | −0.0080 (8) | −0.0010 (8) | 0.0072 (8) |
C4 | 0.0363 (9) | 0.0418 (9) | 0.0473 (9) | −0.0027 (7) | −0.0057 (7) | 0.0083 (8) |
C5 | 0.0326 (8) | 0.0302 (8) | 0.0342 (8) | −0.0006 (6) | 0.0006 (6) | −0.0019 (6) |
C6 | 0.0315 (8) | 0.0316 (8) | 0.0338 (8) | −0.0011 (6) | −0.0004 (6) | −0.0021 (6) |
C7 | 0.0312 (8) | 0.0411 (9) | 0.0377 (8) | −0.0012 (7) | −0.0016 (6) | 0.0023 (7) |
C8 | 0.0448 (10) | 0.0602 (11) | 0.0423 (10) | −0.0167 (9) | −0.0085 (7) | 0.0054 (8) |
C9 | 0.0498 (11) | 0.0662 (12) | 0.0351 (9) | −0.0129 (9) | −0.0054 (8) | 0.0106 (8) |
C10 | 0.0337 (8) | 0.0418 (9) | 0.0435 (9) | −0.0025 (7) | 0.0036 (7) | 0.0046 (7) |
C11 | 0.0416 (9) | 0.0540 (10) | 0.0426 (9) | −0.0147 (8) | −0.0075 (7) | 0.0011 (8) |
C12 | 0.0431 (10) | 0.0551 (10) | 0.0365 (9) | −0.0096 (8) | −0.0061 (7) | 0.0061 (8) |
C13 | 0.0321 (8) | 0.0409 (9) | 0.0391 (9) | −0.0012 (7) | −0.0027 (6) | 0.0027 (7) |
C14 | 0.0732 (15) | 0.0856 (16) | 0.0554 (12) | −0.0237 (13) | 0.0001 (10) | 0.0252 (11) |
O1—C6 | 1.2298 (18) | C4—C5 | 1.379 (2) |
O2—C13 | 1.3179 (19) | C4—H4A | 0.9400 |
O2—H1O2 | 0.96 (3) | C5—C6 | 1.509 (2) |
O3—C13 | 1.2197 (18) | C7—C8 | 1.382 (2) |
O4—C10 | 1.3691 (19) | C7—C12 | 1.383 (2) |
O4—C14 | 1.414 (2) | C7—C13 | 1.483 (2) |
N1—C3 | 1.330 (2) | C8—C9 | 1.388 (2) |
N1—C2 | 1.331 (2) | C8—H8A | 0.9400 |
N2—C6 | 1.324 (2) | C9—C10 | 1.382 (2) |
N2—H1N2 | 0.889 (18) | C9—H9A | 0.9400 |
N2—H2N2 | 0.912 (19) | C10—C11 | 1.376 (2) |
C1—C2 | 1.377 (2) | C11—C12 | 1.375 (2) |
C1—C5 | 1.380 (2) | C11—H11A | 0.9400 |
C1—H1A | 0.9400 | C12—H12A | 0.9400 |
C2—H2A | 0.9400 | C14—H14A | 0.9700 |
C3—C4 | 1.388 (2) | C14—H14B | 0.9700 |
C3—H3A | 0.9400 | C14—H14C | 0.9700 |
C13—O2—H1O2 | 113.9 (13) | C12—C7—C13 | 119.42 (14) |
C10—O4—C14 | 118.06 (14) | C7—C8—C9 | 121.04 (16) |
C3—N1—C2 | 117.43 (14) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 115.5 (11) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 125.7 (12) | C10—C9—C8 | 119.34 (15) |
H1N2—N2—H2N2 | 118.8 (16) | C10—C9—H9A | 120.3 |
C2—C1—C5 | 119.32 (16) | C8—C9—H9A | 120.3 |
C2—C1—H1A | 120.3 | O4—C10—C11 | 115.26 (15) |
C5—C1—H1A | 120.3 | O4—C10—C9 | 124.82 (15) |
N1—C2—C1 | 123.22 (16) | C11—C10—C9 | 119.92 (15) |
N1—C2—H2A | 118.4 | C12—C11—C10 | 120.30 (15) |
C1—C2—H2A | 118.4 | C12—C11—H11A | 119.9 |
N1—C3—C4 | 123.09 (16) | C10—C11—H11A | 119.9 |
N1—C3—H3A | 118.5 | C11—C12—C7 | 120.82 (15) |
C4—C3—H3A | 118.5 | C11—C12—H12A | 119.6 |
C5—C4—C3 | 118.94 (15) | C7—C12—H12A | 119.6 |
C5—C4—H4A | 120.5 | O3—C13—O2 | 122.18 (14) |
C3—C4—H4A | 120.5 | O3—C13—C7 | 123.46 (14) |
C4—C5—C1 | 117.98 (14) | O2—C13—C7 | 114.35 (13) |
C4—C5—C6 | 124.43 (14) | O4—C14—H14A | 109.5 |
C1—C5—C6 | 117.57 (14) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 123.19 (14) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.38 (13) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.41 (14) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.56 (15) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 122.02 (14) | ||
C3—N1—C2—C1 | 1.1 (3) | C7—C8—C9—C10 | 0.6 (3) |
C5—C1—C2—N1 | −0.2 (3) | C14—O4—C10—C11 | −177.76 (18) |
C2—N1—C3—C4 | −1.3 (3) | C14—O4—C10—C9 | 1.6 (3) |
N1—C3—C4—C5 | 0.5 (3) | C8—C9—C10—O4 | 179.32 (17) |
C3—C4—C5—C1 | 0.5 (2) | C8—C9—C10—C11 | −1.4 (3) |
C3—C4—C5—C6 | −177.43 (14) | O4—C10—C11—C12 | −179.93 (16) |
C2—C1—C5—C4 | −0.7 (2) | C9—C10—C11—C12 | 0.7 (3) |
C2—C1—C5—C6 | 177.42 (15) | C10—C11—C12—C7 | 0.7 (3) |
C4—C5—C6—O1 | 172.79 (15) | C8—C7—C12—C11 | −1.5 (3) |
C1—C5—C6—O1 | −5.2 (2) | C13—C7—C12—C11 | 178.20 (16) |
C4—C5—C6—N2 | −5.5 (2) | C8—C7—C13—O3 | −174.12 (17) |
C1—C5—C6—N2 | 176.48 (15) | C12—C7—C13—O3 | 6.2 (3) |
C12—C7—C8—C9 | 0.8 (3) | C8—C7—C13—O2 | 7.0 (2) |
C13—C7—C8—C9 | −178.89 (16) | C12—C7—C13—O2 | −172.70 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···N1 | 0.96 (2) | 1.70 (2) | 2.656 (2) | 174 (2) |
N2—H1N2···O1i | 0.887 (17) | 2.007 (17) | 2.8892 (19) | 173.0 (14) |
N2—H2N2···O3ii | 0.91 (2) | 2.050 (19) | 2.9446 (19) | 166.3 (17) |
C4—H4A···O3ii | 0.94 | 2.55 | 3.446 (2) | 158 |
C11—H11A···O1iii | 0.94 | 2.53 | 3.155 (2) | 124 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z. |
C8H8O3·C6H6N2O | F(000) = 1152 |
Mr = 274.27 | Dx = 1.362 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.246 (2) Å | Cell parameters from 3766 reflections |
b = 5.2132 (6) Å | θ = 2.5–28.1° |
c = 25.372 (2) Å | µ = 0.10 mm−1 |
β = 92.557 (7)° | T = 300 K |
V = 2675.3 (5) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 3250 independent reflections |
Radiation source: fine-focus sealed tube | 2302 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 28.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −25→26 |
Tmin = 0.881, Tmax = 0.969 | k = −6→6 |
15047 measured reflections | l = −33→33 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0765P)2 + 0.7198P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3250 reflections | Δρmax = 0.20 e Å−3 |
194 parameters | Δρmin = −0.23 e Å−3 |
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 | 1.00017 (5) | 1.2472 (2) | 0.54473 (5) | 0.0522 (3) | |
O2 | 0.76761 (6) | 0.2674 (3) | 0.65442 (5) | 0.0665 (4) | |
H1O2 | 0.7957 (12) | 0.386 (5) | 0.6355 (9) | 0.104 (8)* | |
O3 | 0.70521 (6) | 0.2440 (2) | 0.58033 (4) | 0.0541 (3) | |
O4 | 0.56284 (6) | −0.5750 (3) | 0.72112 (5) | 0.0622 (4) | |
N1 | 0.83835 (7) | 0.6021 (3) | 0.60128 (5) | 0.0519 (4) | |
N2 | 0.91656 (7) | 1.3329 (3) | 0.48619 (5) | 0.0470 (3) | |
H1N2 | 0.9399 (10) | 1.468 (4) | 0.4733 (7) | 0.064 (5)* | |
H2N2 | 0.8758 (10) | 1.298 (4) | 0.4702 (8) | 0.060 (5)* | |
C1 | 0.93642 (8) | 0.8435 (3) | 0.58920 (6) | 0.0491 (4) | |
H1A | 0.9805 | 0.8735 | 0.5990 | 0.059* | |
C2 | 0.90175 (9) | 0.6541 (4) | 0.61361 (7) | 0.0554 (4) | |
H2A | 0.9234 | 0.5578 | 0.6399 | 0.066* | |
C3 | 0.80879 (8) | 0.7392 (3) | 0.56299 (7) | 0.0556 (4) | |
H3A | 0.7649 | 0.7029 | 0.5536 | 0.067* | |
C4 | 0.83981 (8) | 0.9333 (3) | 0.53634 (7) | 0.0508 (4) | |
H4A | 0.8172 | 1.0250 | 0.5098 | 0.061* | |
C5 | 0.90535 (7) | 0.9884 (3) | 0.55007 (5) | 0.0393 (3) | |
C6 | 0.94431 (7) | 1.2003 (3) | 0.52584 (6) | 0.0392 (3) | |
C7 | 0.67715 (7) | −0.0166 (3) | 0.65313 (6) | 0.0453 (4) | |
C8 | 0.68810 (9) | −0.0724 (4) | 0.70601 (7) | 0.0601 (5) | |
H8A | 0.7210 | 0.0150 | 0.7254 | 0.072* | |
C9 | 0.65077 (9) | −0.2566 (4) | 0.73060 (7) | 0.0626 (5) | |
H9A | 0.6582 | −0.2914 | 0.7663 | 0.075* | |
C10 | 0.60241 (8) | −0.3879 (3) | 0.70155 (6) | 0.0494 (4) | |
C11 | 0.59064 (9) | −0.3317 (4) | 0.64895 (7) | 0.0568 (4) | |
H11A | 0.5577 | −0.4189 | 0.6295 | 0.068* | |
C12 | 0.62746 (8) | −0.1469 (4) | 0.62502 (7) | 0.0541 (4) | |
H12A | 0.6189 | −0.1090 | 0.5896 | 0.065* | |
C13 | 0.71701 (7) | 0.1766 (3) | 0.62578 (6) | 0.0458 (4) | |
C14 | 0.57079 (12) | −0.6368 (5) | 0.77512 (9) | 0.0875 (7) | |
H14A | 0.5429 | −0.7797 | 0.7829 | 0.131* | |
H14B | 0.5587 | −0.4917 | 0.7959 | 0.131* | |
H14C | 0.6161 | −0.6810 | 0.7834 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0455 (6) | 0.0536 (7) | 0.0563 (7) | −0.0124 (5) | −0.0110 (5) | 0.0103 (5) |
O2 | 0.0598 (8) | 0.0831 (9) | 0.0553 (8) | −0.0311 (7) | −0.0127 (6) | 0.0175 (7) |
O3 | 0.0488 (6) | 0.0649 (7) | 0.0481 (7) | −0.0058 (5) | −0.0052 (5) | 0.0102 (5) |
O4 | 0.0594 (7) | 0.0675 (8) | 0.0598 (8) | −0.0156 (6) | 0.0030 (6) | 0.0137 (6) |
N1 | 0.0531 (8) | 0.0522 (8) | 0.0507 (8) | −0.0101 (6) | 0.0047 (6) | 0.0052 (6) |
N2 | 0.0463 (8) | 0.0478 (7) | 0.0461 (8) | −0.0076 (6) | −0.0060 (6) | 0.0082 (6) |
C1 | 0.0446 (8) | 0.0543 (9) | 0.0478 (9) | −0.0060 (7) | −0.0044 (7) | 0.0076 (7) |
C2 | 0.0559 (10) | 0.0579 (10) | 0.0517 (10) | −0.0051 (8) | −0.0045 (7) | 0.0141 (8) |
C3 | 0.0427 (8) | 0.0594 (10) | 0.0645 (11) | −0.0096 (7) | 0.0009 (8) | 0.0091 (8) |
C4 | 0.0431 (8) | 0.0536 (9) | 0.0552 (10) | −0.0044 (7) | −0.0043 (7) | 0.0104 (8) |
C5 | 0.0398 (7) | 0.0393 (7) | 0.0387 (8) | −0.0011 (6) | 0.0022 (6) | −0.0024 (6) |
C6 | 0.0391 (7) | 0.0398 (7) | 0.0386 (8) | −0.0021 (6) | −0.0005 (6) | −0.0015 (6) |
C7 | 0.0394 (8) | 0.0518 (9) | 0.0445 (9) | −0.0027 (6) | −0.0003 (6) | 0.0029 (7) |
C8 | 0.0564 (10) | 0.0740 (12) | 0.0492 (10) | −0.0212 (9) | −0.0076 (8) | 0.0052 (8) |
C9 | 0.0620 (11) | 0.0831 (13) | 0.0420 (9) | −0.0163 (10) | −0.0055 (8) | 0.0123 (9) |
C10 | 0.0446 (8) | 0.0526 (9) | 0.0512 (9) | −0.0038 (7) | 0.0049 (7) | 0.0060 (7) |
C11 | 0.0521 (9) | 0.0665 (11) | 0.0510 (10) | −0.0164 (8) | −0.0063 (7) | 0.0027 (8) |
C12 | 0.0521 (9) | 0.0673 (11) | 0.0424 (9) | −0.0112 (8) | −0.0062 (7) | 0.0068 (8) |
C13 | 0.0397 (8) | 0.0527 (9) | 0.0445 (9) | −0.0022 (7) | −0.0032 (6) | 0.0036 (7) |
C14 | 0.0902 (16) | 0.1047 (18) | 0.0674 (14) | −0.0305 (14) | 0.0024 (11) | 0.0290 (13) |
O1—C6 | 1.2329 (17) | C4—C5 | 1.387 (2) |
O2—C13 | 1.3172 (19) | C4—H4A | 0.9300 |
O2—H1O2 | 0.98 (3) | C5—C6 | 1.505 (2) |
O3—C13 | 1.2189 (18) | C7—C8 | 1.381 (2) |
O4—C10 | 1.370 (2) | C7—C12 | 1.385 (2) |
O4—C14 | 1.410 (2) | C7—C13 | 1.482 (2) |
N1—C3 | 1.327 (2) | C8—C9 | 1.388 (2) |
N1—C2 | 1.335 (2) | C8—H8A | 0.9300 |
N2—C6 | 1.3248 (19) | C9—C10 | 1.381 (2) |
N2—H1N2 | 0.92 (2) | C9—H9A | 0.9300 |
N2—H2N2 | 0.92 (2) | C10—C11 | 1.377 (2) |
C1—C2 | 1.375 (2) | C11—C12 | 1.376 (2) |
C1—C5 | 1.377 (2) | C11—H11A | 0.9300 |
C1—H1A | 0.9300 | C12—H12A | 0.9300 |
C2—H2A | 0.9300 | C14—H14A | 0.9600 |
C3—C4 | 1.383 (2) | C14—H14B | 0.9600 |
C3—H3A | 0.9300 | C14—H14C | 0.9600 |
C13—O2—H1O2 | 114.2 (14) | C12—C7—C13 | 119.35 (14) |
C10—O4—C14 | 118.15 (15) | C7—C8—C9 | 121.04 (16) |
C3—N1—C2 | 117.36 (14) | C7—C8—H8A | 119.5 |
C6—N2—H1N2 | 117.7 (12) | C9—C8—H8A | 119.5 |
C6—N2—H2N2 | 125.0 (12) | C10—C9—C8 | 119.38 (16) |
H1N2—N2—H2N2 | 117.3 (17) | C10—C9—H9A | 120.3 |
C2—C1—C5 | 119.52 (15) | C8—C9—H9A | 120.3 |
C2—C1—H1A | 120.2 | O4—C10—C11 | 115.11 (15) |
C5—C1—H1A | 120.2 | O4—C10—C9 | 124.88 (15) |
N1—C2—C1 | 123.03 (16) | C11—C10—C9 | 120.01 (15) |
N1—C2—H2A | 118.5 | C12—C11—C10 | 120.21 (15) |
C1—C2—H2A | 118.5 | C12—C11—H11A | 119.9 |
N1—C3—C4 | 123.52 (15) | C10—C11—H11A | 119.9 |
N1—C3—H3A | 118.2 | C11—C12—C7 | 120.76 (15) |
C4—C3—H3A | 118.2 | C11—C12—H12A | 119.6 |
C3—C4—C5 | 118.60 (15) | C7—C12—H12A | 119.6 |
C3—C4—H4A | 120.7 | O3—C13—O2 | 122.21 (14) |
C5—C4—H4A | 120.7 | O3—C13—C7 | 123.44 (14) |
C1—C5—C4 | 117.95 (14) | O2—C13—C7 | 114.34 (13) |
C1—C5—C6 | 117.80 (13) | O4—C14—H14A | 109.5 |
C4—C5—C6 | 124.23 (14) | O4—C14—H14B | 109.5 |
O1—C6—N2 | 122.84 (14) | H14A—C14—H14B | 109.5 |
O1—C6—C5 | 118.39 (13) | O4—C14—H14C | 109.5 |
N2—C6—C5 | 118.75 (13) | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.59 (15) | H14B—C14—H14C | 109.5 |
C8—C7—C13 | 122.06 (14) | ||
C3—N1—C2—C1 | 1.1 (3) | C7—C8—C9—C10 | 0.7 (3) |
C5—C1—C2—N1 | −0.1 (3) | C14—O4—C10—C11 | −178.06 (19) |
C2—N1—C3—C4 | −1.2 (3) | C14—O4—C10—C9 | 1.2 (3) |
N1—C3—C4—C5 | 0.1 (3) | C8—C9—C10—O4 | 179.40 (18) |
C2—C1—C5—C4 | −1.0 (2) | C8—C9—C10—C11 | −1.4 (3) |
C2—C1—C5—C6 | 177.70 (15) | O4—C10—C11—C12 | −179.96 (17) |
C3—C4—C5—C1 | 0.9 (2) | C9—C10—C11—C12 | 0.7 (3) |
C3—C4—C5—C6 | −177.63 (14) | C10—C11—C12—C7 | 0.6 (3) |
C1—C5—C6—O1 | −5.5 (2) | C8—C7—C12—C11 | −1.3 (3) |
C4—C5—C6—O1 | 173.08 (15) | C13—C7—C12—C11 | 178.43 (17) |
C1—C5—C6—N2 | 176.37 (14) | C8—C7—C13—O3 | −174.11 (17) |
C4—C5—C6—N2 | −5.1 (2) | C12—C7—C13—O3 | 6.1 (3) |
C12—C7—C8—C9 | 0.7 (3) | C8—C7—C13—O2 | 7.2 (2) |
C13—C7—C8—C9 | −179.08 (17) | C12—C7—C13—O2 | −172.58 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···N1 | 0.98 (2) | 1.68 (2) | 2.662 (2) | 175 (2) |
N2—H1N2···O1i | 0.92 (2) | 1.98 (2) | 2.8927 (19) | 171.0 (16) |
N2—H2N2···O3ii | 0.92 (2) | 2.06 (2) | 2.9614 (18) | 167.4 (18) |
C4—H4A···O3ii | 0.93 | 2.58 | 3.461 (2) | 159 |
C11—H11A···O1iii | 0.93 | 2.56 | 3.180 (2) | 124 |
Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+3/2, y+1, −z+1; (iii) x−1/2, −y+1, z. |