Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104005506/og0001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768104005506/og0001alphasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768104005506/og0001gammasup3.hkl |
CCDC references: 241471; 241472
For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C17H12N4O4 | F(000) = 1392 |
Mr = 336.31 | Dx = 1.478 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 14.0059 (1) Å | µ = 0.11 mm−1 |
b = 5.1399 (1) Å | T = 78 K |
c = 41.9853 (6) Å | Block, colorless |
V = 3022.48 (8) Å3 | 0.35 × 0.10 × 0.05 mm |
Z = 8 |
Siemens CCD diffractometer | 6678 independent reflections |
Radiation source: fine-focus sealed tube | 4589 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
ω–scan | θmax = 27.5°, θmin = 1.9° |
Absorption correction: empirical SADABS (Sheldrick, 1996) | h = −15→18 |
Tmin = 0.674, Tmax = 1.000 | k = −6→6 |
19857 measured reflections | l = −47→54 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.179 | (Δ/σ)max = 0.026 |
S = 1.03 | Δρmax = 1.13 e Å−3 |
6678 reflections | Δρmin = −0.27 e Å−3 |
452 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0104 (11) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −1.0 (19) |
C17H12N4O4 | V = 3022.48 (8) Å3 |
Mr = 336.31 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.0059 (1) Å | µ = 0.11 mm−1 |
b = 5.1399 (1) Å | T = 78 K |
c = 41.9853 (6) Å | 0.35 × 0.10 × 0.05 mm |
Siemens CCD diffractometer | 6678 independent reflections |
Absorption correction: empirical SADABS (Sheldrick, 1996) | 4589 reflections with I > 2σ(I) |
Tmin = 0.674, Tmax = 1.000 | Rint = 0.080 |
19857 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.179 | Δρmax = 1.13 e Å−3 |
S = 1.03 | Δρmin = −0.27 e Å−3 |
6678 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
452 parameters | Absolute structure parameter: −1.0 (19) |
1 restraint |
Experimental. alpha form of 6-(2',4'-dinitrobenzyl)-2,2'-bipyridine |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.3904 (3) | 0.4697 (7) | 0.76327 (8) | 0.0286 (8) | |
O2 | 0.4525 (2) | 0.0817 (7) | 0.75954 (9) | 0.0335 (9) | |
O3 | 0.3690 (3) | −0.5085 (7) | 0.84278 (9) | 0.0370 (9) | |
O4 | 0.2391 (3) | −0.4489 (8) | 0.87018 (8) | 0.0400 (10) | |
O5 | 0.3681 (2) | 0.9674 (7) | 0.96382 (8) | 0.0257 (7) | |
O6 | 0.3048 (2) | 0.5852 (7) | 0.96808 (9) | 0.0316 (9) | |
O7 | 0.3880 (3) | −0.0107 (7) | 0.88457 (8) | 0.0313 (9) | |
O8 | 0.5188 (3) | 0.0523 (7) | 0.85709 (9) | 0.0386 (9) | |
N1 | 0.2448 (3) | 0.1759 (9) | 0.71644 (9) | 0.0175 (8) | |
N2 | 0.3891 (4) | 0.2329 (8) | 0.76866 (15) | 0.0235 (13) | |
N3 | 0.2933 (3) | −0.3954 (8) | 0.84807 (10) | 0.0289 (10) | |
N4 | 0.3339 (3) | −0.0839 (7) | 0.64269 (9) | 0.0218 (8) | |
N5 | 0.5117 (3) | 0.6786 (9) | 1.01057 (9) | 0.0179 (8) | |
N6 | 0.3683 (4) | 0.7339 (8) | 0.95974 (13) | 0.0182 (12) | |
N7 | 0.4645 (3) | 0.1024 (7) | 0.87945 (10) | 0.0262 (9) | |
N8 | 0.4164 (3) | 0.4221 (7) | 1.08432 (9) | 0.0205 (8) | |
C1 | 0.2465 (3) | 0.1251 (8) | 0.68501 (10) | 0.0169 (9) | |
C2 | 0.1879 (4) | 0.2471 (8) | 0.66291 (16) | 0.0159 (15) | |
H2 | 0.1919 | 0.2081 | 0.6408 | 0.019* | |
C3 | 0.1224 (3) | 0.4303 (8) | 0.67458 (11) | 0.0204 (9) | |
H3 | 0.0795 | 0.5147 | 0.6604 | 0.025* | |
C4 | 0.1206 (3) | 0.4877 (8) | 0.70673 (11) | 0.0201 (9) | |
H4 | 0.0775 | 0.6144 | 0.7148 | 0.024* | |
C5 | 0.1821 (3) | 0.3584 (9) | 0.72688 (10) | 0.0177 (9) | |
C6 | 0.1849 (3) | 0.4290 (9) | 0.76193 (11) | 0.0225 (10) | |
H6A | 0.1202 | 0.4869 | 0.7683 | 0.027* | |
H6B | 0.2284 | 0.5792 | 0.7646 | 0.027* | |
C7 | 0.2166 (4) | 0.2147 (10) | 0.78485 (14) | 0.0189 (12) | |
C8 | 0.3100 (3) | 0.1193 (8) | 0.78638 (10) | 0.0161 (9) | |
C9 | 0.3353 (3) | −0.0801 (8) | 0.80682 (11) | 0.0207 (9) | |
H9 | 0.3991 | −0.1423 | 0.8076 | 0.025* | |
C10 | 0.2661 (4) | −0.1861 (11) | 0.82598 (12) | 0.0234 (10) | |
C11 | 0.1725 (4) | −0.1019 (10) | 0.82508 (11) | 0.0266 (11) | |
H11 | 0.1254 | −0.1773 | 0.8385 | 0.032* | |
C12 | 0.1491 (3) | 0.0973 (9) | 0.80387 (11) | 0.0248 (10) | |
H12 | 0.0846 | 0.1537 | 0.8025 | 0.030* | |
C13 | 0.3176 (3) | −0.0769 (8) | 0.67411 (10) | 0.0168 (9) | |
C14 | 0.3624 (4) | −0.2407 (8) | 0.69483 (15) | 0.0165 (15) | |
H14 | 0.3495 | −0.2263 | 0.7170 | 0.020* | |
C15 | 0.4258 (3) | −0.4260 (9) | 0.68438 (11) | 0.0195 (9) | |
H15 | 0.4562 | −0.5413 | 0.6989 | 0.023* | |
C16 | 0.4436 (3) | −0.4385 (9) | 0.65218 (11) | 0.0193 (9) | |
H16 | 0.4861 | −0.5645 | 0.6437 | 0.023* | |
C17 | 0.3977 (4) | −0.2628 (9) | 0.63272 (16) | 0.0197 (15) | |
H17 | 0.4122 | −0.2679 | 0.6106 | 0.024* | |
C18 | 0.5055 (3) | 0.6290 (8) | 1.04231 (10) | 0.0158 (9) | |
C19 | 0.5641 (5) | 0.7588 (9) | 1.06391 (18) | 0.0238 (17) | |
H19 | 0.5596 | 0.7201 | 1.0860 | 0.029* | |
C20 | 0.6286 (3) | 0.9427 (9) | 1.05353 (11) | 0.0228 (10) | |
H20 | 0.6685 | 1.0321 | 1.0682 | 0.027* | |
C21 | 0.6338 (3) | 0.9946 (9) | 1.02094 (10) | 0.0191 (9) | |
H21 | 0.6776 | 1.1190 | 1.0128 | 0.023* | |
C22 | 0.5722 (3) | 0.8570 (8) | 1.00065 (10) | 0.0168 (9) | |
C23 | 0.5727 (3) | 0.9305 (9) | 0.96536 (10) | 0.0199 (9) | |
H23A | 0.5299 | 1.0816 | 0.9622 | 0.024* | |
H23B | 0.6380 | 0.9849 | 0.9593 | 0.024* | |
C24 | 0.5419 (4) | 0.7169 (10) | 0.94392 (15) | 0.0182 (12) | |
C25 | 0.4484 (3) | 0.6180 (9) | 0.94088 (10) | 0.0180 (9) | |
C26 | 0.4212 (3) | 0.4185 (9) | 0.92063 (10) | 0.0196 (9) | |
H26 | 0.3573 | 0.3566 | 0.9200 | 0.023* | |
C27 | 0.4917 (4) | 0.3127 (11) | 0.90115 (11) | 0.0204 (10) | |
C28 | 0.5863 (4) | 0.3984 (10) | 0.90207 (11) | 0.0259 (10) | |
H28 | 0.6333 | 0.3259 | 0.8884 | 0.031* | |
C29 | 0.6093 (3) | 0.5941 (9) | 0.92376 (10) | 0.0216 (10) | |
H29 | 0.6740 | 0.6482 | 0.9251 | 0.026* | |
C30 | 0.4359 (3) | 0.4318 (8) | 1.05291 (9) | 0.0145 (9) | |
C31 | 0.3939 (4) | 0.2593 (8) | 1.02999 (17) | 0.0200 (15) | |
H31 | 0.4084 | 0.2709 | 1.0079 | 0.024* | |
C32 | 0.3298 (3) | 0.0713 (9) | 1.04196 (11) | 0.0214 (10) | |
H32 | 0.3001 | −0.0492 | 1.0279 | 0.026* | |
C33 | 0.3101 (3) | 0.0636 (9) | 1.07481 (12) | 0.0224 (10) | |
H33 | 0.2670 | −0.0612 | 1.0832 | 0.027* | |
C34 | 0.3552 (4) | 0.2427 (9) | 1.09487 (18) | 0.0233 (17) | |
H34 | 0.3417 | 0.2363 | 1.1170 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.036 (2) | 0.0223 (19) | 0.0270 (18) | −0.0014 (16) | 0.0015 (15) | 0.0025 (15) |
O2 | 0.0202 (18) | 0.037 (2) | 0.043 (2) | 0.0075 (15) | 0.0023 (16) | −0.0013 (17) |
O3 | 0.057 (3) | 0.025 (2) | 0.0285 (19) | 0.0065 (19) | −0.0099 (18) | −0.0057 (15) |
O4 | 0.047 (2) | 0.045 (2) | 0.028 (2) | −0.0183 (19) | −0.0095 (17) | 0.0155 (17) |
O5 | 0.0271 (18) | 0.0256 (19) | 0.0242 (18) | 0.0038 (15) | 0.0016 (14) | −0.0019 (14) |
O6 | 0.0203 (18) | 0.037 (2) | 0.038 (2) | −0.0060 (16) | 0.0059 (16) | 0.0030 (17) |
O7 | 0.050 (2) | 0.0214 (19) | 0.0228 (18) | −0.0073 (17) | −0.0091 (16) | 0.0000 (14) |
O8 | 0.045 (2) | 0.040 (2) | 0.031 (2) | 0.0119 (18) | −0.0044 (17) | −0.0118 (18) |
N1 | 0.0139 (19) | 0.0194 (18) | 0.019 (2) | 0.0037 (18) | 0.0001 (15) | −0.0020 (19) |
N2 | 0.020 (2) | 0.026 (3) | 0.025 (3) | 0.0025 (16) | 0.000 (2) | 0.0022 (16) |
N3 | 0.035 (2) | 0.026 (2) | 0.025 (2) | −0.004 (2) | −0.008 (2) | 0.0003 (18) |
N4 | 0.021 (2) | 0.024 (2) | 0.020 (2) | 0.0008 (17) | −0.0016 (16) | −0.0018 (16) |
N5 | 0.020 (2) | 0.0154 (18) | 0.018 (2) | 0.0031 (18) | −0.0033 (16) | −0.0012 (19) |
N6 | 0.019 (2) | 0.023 (3) | 0.013 (2) | 0.0026 (15) | −0.0063 (19) | 0.0050 (14) |
N7 | 0.040 (3) | 0.019 (2) | 0.020 (2) | 0.0074 (19) | −0.0108 (19) | 0.0002 (17) |
N8 | 0.0188 (19) | 0.020 (2) | 0.023 (2) | 0.0033 (16) | −0.0033 (16) | 0.0013 (15) |
C1 | 0.012 (2) | 0.017 (2) | 0.021 (2) | −0.0008 (17) | 0.0024 (16) | 0.0012 (17) |
C2 | 0.020 (3) | 0.019 (4) | 0.009 (3) | 0.0025 (16) | 0.001 (2) | 0.0014 (14) |
C3 | 0.018 (2) | 0.024 (2) | 0.019 (2) | 0.0010 (19) | −0.0046 (18) | 0.0055 (18) |
C4 | 0.018 (2) | 0.019 (2) | 0.024 (2) | 0.0014 (18) | 0.0000 (18) | −0.0004 (18) |
C5 | 0.016 (2) | 0.022 (3) | 0.016 (2) | 0.0023 (19) | 0.0026 (17) | −0.0025 (18) |
C6 | 0.019 (2) | 0.020 (2) | 0.028 (3) | 0.0042 (18) | −0.0029 (19) | −0.0001 (19) |
C7 | 0.024 (3) | 0.024 (2) | 0.008 (2) | 0.007 (2) | −0.0089 (19) | 0.0012 (19) |
C8 | 0.013 (2) | 0.018 (2) | 0.017 (2) | −0.0003 (17) | −0.0005 (16) | −0.0047 (17) |
C9 | 0.021 (2) | 0.014 (2) | 0.027 (2) | −0.0019 (19) | −0.0050 (19) | −0.0026 (18) |
C10 | 0.033 (3) | 0.019 (2) | 0.018 (3) | −0.006 (2) | −0.009 (2) | −0.003 (2) |
C11 | 0.024 (2) | 0.033 (3) | 0.023 (3) | −0.013 (2) | 0.0003 (19) | −0.0021 (19) |
C12 | 0.019 (2) | 0.037 (3) | 0.019 (2) | 0.002 (2) | −0.0008 (18) | −0.005 (2) |
C13 | 0.013 (2) | 0.017 (2) | 0.020 (2) | 0.0008 (17) | 0.0009 (17) | −0.0028 (17) |
C14 | 0.015 (3) | 0.022 (4) | 0.013 (3) | −0.0030 (16) | 0.001 (2) | 0.0031 (15) |
C15 | 0.020 (2) | 0.015 (2) | 0.023 (2) | −0.0030 (19) | −0.0049 (18) | 0.0042 (17) |
C16 | 0.017 (2) | 0.016 (2) | 0.024 (2) | −0.0013 (17) | 0.0029 (18) | −0.0067 (18) |
C17 | 0.021 (3) | 0.027 (4) | 0.012 (3) | 0.0040 (18) | 0.007 (2) | −0.0020 (16) |
C18 | 0.0127 (19) | 0.019 (2) | 0.016 (2) | 0.0043 (17) | −0.0023 (16) | −0.0012 (17) |
C19 | 0.024 (3) | 0.028 (5) | 0.020 (4) | 0.0004 (19) | −0.003 (3) | 0.0018 (18) |
C20 | 0.018 (2) | 0.026 (2) | 0.025 (2) | −0.002 (2) | −0.0066 (19) | −0.0011 (19) |
C21 | 0.012 (2) | 0.022 (2) | 0.023 (2) | −0.0043 (17) | −0.0002 (17) | −0.0015 (18) |
C22 | 0.010 (2) | 0.018 (2) | 0.022 (2) | 0.0029 (17) | −0.0028 (17) | −0.0036 (18) |
C23 | 0.021 (2) | 0.025 (2) | 0.013 (2) | −0.0080 (19) | 0.0000 (17) | 0.0031 (18) |
C24 | 0.012 (2) | 0.025 (3) | 0.018 (3) | −0.0011 (19) | 0.0013 (19) | 0.012 (2) |
C25 | 0.018 (2) | 0.022 (2) | 0.015 (2) | 0.0000 (18) | −0.0016 (17) | 0.0011 (17) |
C26 | 0.021 (2) | 0.022 (2) | 0.016 (2) | −0.0034 (19) | −0.0056 (18) | 0.0046 (18) |
C27 | 0.031 (3) | 0.015 (2) | 0.015 (2) | 0.003 (2) | −0.003 (2) | 0.000 (2) |
C28 | 0.029 (3) | 0.028 (3) | 0.021 (3) | 0.003 (2) | 0.001 (2) | 0.0004 (18) |
C29 | 0.018 (2) | 0.030 (3) | 0.017 (2) | 0.002 (2) | −0.0009 (17) | 0.0018 (19) |
C30 | 0.017 (2) | 0.017 (2) | 0.010 (2) | 0.0059 (17) | −0.0036 (16) | −0.0028 (16) |
C31 | 0.021 (3) | 0.017 (4) | 0.022 (3) | 0.0039 (17) | 0.000 (2) | 0.0015 (16) |
C32 | 0.018 (2) | 0.021 (2) | 0.026 (2) | 0.0015 (19) | 0.0028 (19) | −0.0002 (19) |
C33 | 0.021 (2) | 0.018 (2) | 0.028 (2) | −0.0011 (19) | 0.0030 (19) | 0.0067 (19) |
C34 | 0.020 (3) | 0.026 (4) | 0.025 (4) | 0.0069 (18) | −0.007 (3) | 0.0032 (17) |
O1—N2 | 1.238 (5) | C9—H9 | 0.9500 |
O1—C6 | 2.887 (6) | C10—C11 | 1.382 (7) |
O1—N1 | 3.210 (5) | C11—C12 | 1.396 (7) |
O2—N2 | 1.241 (6) | C11—H11 | 0.9500 |
O3—N3 | 1.230 (5) | C12—H12 | 0.9500 |
O4—N3 | 1.230 (6) | C13—C14 | 1.364 (7) |
O5—N6 | 1.212 (5) | C14—C15 | 1.374 (7) |
O5—C23 | 2.873 (6) | C14—H14 | 0.9500 |
O5—N5 | 3.178 (5) | C15—C16 | 1.376 (7) |
O6—N6 | 1.224 (6) | C15—H15 | 0.9500 |
O7—N7 | 1.238 (5) | C16—C17 | 1.377 (8) |
O8—N7 | 1.235 (6) | C16—H16 | 0.9500 |
N1—C1 | 1.345 (6) | C17—H17 | 0.9500 |
N1—C5 | 1.358 (6) | C18—C19 | 1.393 (8) |
N1—C6 | 2.459 (6) | C18—C30 | 1.475 (6) |
N2—C8 | 1.456 (7) | C19—C20 | 1.378 (8) |
N3—C10 | 1.470 (7) | C19—H19 | 0.9500 |
N4—C13 | 1.340 (6) | C20—C21 | 1.396 (7) |
N4—C17 | 1.349 (6) | C20—H20 | 0.9500 |
N5—C22 | 1.316 (6) | C21—C22 | 1.403 (6) |
N5—C18 | 1.360 (6) | C21—H21 | 0.9500 |
N5—C23 | 2.451 (6) | C22—C23 | 1.529 (6) |
N6—C25 | 1.496 (7) | C23—C24 | 1.484 (7) |
N7—C27 | 1.464 (7) | C23—H23A | 0.9900 |
N8—C34 | 1.334 (7) | C23—H23B | 0.9900 |
N8—C30 | 1.348 (5) | C24—C25 | 1.411 (7) |
C1—C2 | 1.389 (7) | C24—C29 | 1.417 (7) |
C1—C13 | 1.509 (6) | C25—C26 | 1.386 (6) |
C2—C3 | 1.403 (7) | C26—C27 | 1.393 (7) |
C2—H2 | 0.9500 | C26—H26 | 0.9500 |
C3—C4 | 1.382 (6) | C27—C28 | 1.396 (7) |
C3—H3 | 0.9500 | C28—C29 | 1.395 (7) |
C4—C5 | 1.378 (6) | C28—H28 | 0.9500 |
C4—H4 | 0.9500 | C29—H29 | 0.9500 |
C5—C6 | 1.516 (6) | C30—C31 | 1.435 (7) |
C6—C7 | 1.529 (7) | C31—C32 | 1.411 (7) |
C6—H6A | 0.9900 | C31—H31 | 0.9500 |
C6—H6B | 0.9900 | C32—C33 | 1.407 (7) |
C7—C12 | 1.377 (8) | C32—H32 | 0.9500 |
C7—C8 | 1.399 (7) | C33—C34 | 1.398 (8) |
C8—C9 | 1.383 (6) | C33—H33 | 0.9500 |
C9—C10 | 1.372 (7) | C34—H34 | 0.9500 |
N2—O1—C6 | 85.3 (3) | C11—C12—H12 | 119.0 |
N2—O1—N1 | 68.9 (3) | N4—C13—C14 | 122.2 (4) |
C6—O1—N1 | 47.20 (12) | N4—C13—C1 | 115.5 (4) |
N6—O5—C23 | 86.3 (3) | C14—C13—C1 | 122.4 (4) |
N6—O5—N5 | 67.9 (3) | C13—C14—C15 | 121.5 (6) |
C23—O5—N5 | 47.46 (12) | C13—C14—H14 | 119.3 |
C1—N1—C5 | 117.5 (4) | C15—C14—H14 | 119.3 |
C1—N1—C6 | 150.5 (3) | C16—C15—C14 | 117.6 (5) |
C5—N1—C6 | 33.2 (2) | C16—C15—H15 | 121.2 |
C1—N1—O1 | 132.9 (3) | C14—C15—H15 | 121.2 |
C5—N1—O1 | 83.6 (3) | C15—C16—C17 | 117.9 (4) |
C6—N1—O1 | 59.49 (15) | C15—C16—H16 | 121.1 |
O1—N2—O2 | 123.3 (5) | C17—C16—H16 | 121.1 |
O1—N2—C8 | 119.9 (5) | N4—C17—C16 | 124.9 (6) |
O2—N2—C8 | 116.8 (4) | N4—C17—H17 | 117.6 |
O4—N3—O3 | 124.2 (4) | C16—C17—H17 | 117.6 |
O4—N3—C10 | 118.7 (4) | N5—C18—C19 | 120.7 (5) |
O3—N3—C10 | 117.1 (4) | N5—C18—C30 | 117.8 (4) |
C13—N4—C17 | 115.9 (4) | C19—C18—C30 | 121.5 (4) |
C22—N5—C18 | 118.8 (4) | C20—C19—C18 | 120.6 (6) |
C22—N5—C23 | 33.2 (2) | C20—C19—H19 | 119.7 |
C18—N5—C23 | 151.7 (3) | C18—C19—H19 | 119.7 |
C22—N5—O5 | 83.5 (3) | C19—C20—C21 | 118.4 (5) |
C18—N5—O5 | 130.7 (3) | C19—C20—H20 | 120.8 |
C23—N5—O5 | 59.72 (15) | C21—C20—H20 | 120.8 |
O5—N6—O6 | 125.1 (5) | C20—C21—C22 | 117.8 (4) |
O5—N6—C25 | 118.1 (5) | C20—C21—H21 | 121.1 |
O6—N6—C25 | 116.6 (4) | C22—C21—H21 | 121.1 |
O8—N7—O7 | 124.6 (4) | N5—C22—C21 | 123.7 (4) |
O8—N7—C27 | 117.8 (4) | N5—C22—C23 | 118.8 (4) |
O7—N7—C27 | 117.6 (4) | C21—C22—C23 | 117.5 (4) |
C34—N8—C30 | 118.8 (5) | C24—C23—C22 | 113.8 (4) |
N1—C1—C2 | 123.9 (4) | C24—C23—N5 | 88.7 (3) |
N1—C1—C13 | 116.3 (4) | C22—C23—N5 | 28.1 (2) |
C2—C1—C13 | 119.9 (4) | C24—C23—O5 | 75.2 (3) |
C1—C2—C3 | 117.1 (5) | C22—C23—O5 | 92.0 (3) |
C1—C2—H2 | 121.4 | N5—C23—O5 | 72.82 (16) |
C3—C2—H2 | 121.4 | C24—C23—H23A | 108.8 |
C4—C3—C2 | 119.8 (5) | C22—C23—H23A | 108.8 |
C4—C3—H3 | 120.1 | N5—C23—H23A | 107.9 |
C2—C3—H3 | 120.1 | O5—C23—H23A | 48.8 |
C5—C4—C3 | 119.0 (4) | C24—C23—H23B | 108.8 |
C5—C4—H4 | 120.5 | C22—C23—H23B | 108.8 |
C3—C4—H4 | 120.5 | N5—C23—H23B | 132.1 |
N1—C5—C4 | 122.7 (4) | O5—C23—H23B | 153.9 |
N1—C5—C6 | 117.5 (4) | H23A—C23—H23B | 107.7 |
C4—C5—C6 | 119.7 (4) | C25—C24—C29 | 113.8 (5) |
C5—C6—C7 | 116.5 (4) | C25—C24—C23 | 126.3 (5) |
C5—C6—N1 | 29.3 (2) | C29—C24—C23 | 119.9 (4) |
C7—C6—N1 | 90.5 (3) | C26—C25—C24 | 125.3 (4) |
C5—C6—O1 | 93.5 (3) | C26—C25—N6 | 114.4 (4) |
C7—C6—O1 | 75.5 (3) | C24—C25—N6 | 120.3 (4) |
N1—C6—O1 | 73.30 (16) | C25—C26—C27 | 117.0 (4) |
C5—C6—H6A | 108.2 | C25—C26—H26 | 121.5 |
C7—C6—H6A | 108.2 | C27—C26—H26 | 121.5 |
N1—C6—H6A | 133.0 | C26—C27—C28 | 122.2 (5) |
O1—C6—H6A | 152.2 | C26—C27—N7 | 118.0 (5) |
C5—C6—H6B | 108.2 | C28—C27—N7 | 119.8 (4) |
C7—C6—H6B | 108.2 | C29—C28—C27 | 117.7 (4) |
N1—C6—H6B | 106.9 | C29—C28—H28 | 121.2 |
O1—C6—H6B | 47.7 | C27—C28—H28 | 121.2 |
H6A—C6—H6B | 107.3 | C28—C29—C24 | 123.9 (5) |
C12—C7—C8 | 117.5 (5) | C28—C29—H29 | 118.1 |
C12—C7—C6 | 118.8 (4) | C24—C29—H29 | 118.1 |
C8—C7—C6 | 123.6 (5) | N8—C30—C31 | 123.3 (4) |
C9—C8—C7 | 121.8 (4) | N8—C30—C18 | 117.1 (4) |
C9—C8—N2 | 114.8 (4) | C31—C30—C18 | 119.6 (4) |
C7—C8—N2 | 123.2 (5) | C32—C31—C30 | 116.5 (6) |
C10—C9—C8 | 118.5 (4) | C32—C31—H31 | 121.8 |
C10—C9—H9 | 120.7 | C30—C31—H31 | 121.8 |
C8—C9—H9 | 120.7 | C33—C32—C31 | 119.5 (5) |
C9—C10—C11 | 122.0 (5) | C33—C32—H32 | 120.2 |
C9—C10—N3 | 118.5 (5) | C31—C32—H32 | 120.2 |
C11—C10—N3 | 119.4 (5) | C34—C33—C32 | 118.9 (5) |
C10—C11—C12 | 118.0 (5) | C34—C33—H33 | 120.5 |
C10—C11—H11 | 121.0 | C32—C33—H33 | 120.5 |
C12—C11—H11 | 121.0 | N8—C34—C33 | 123.0 (6) |
C7—C12—C11 | 122.0 (4) | N8—C34—H34 | 118.5 |
C7—C12—H12 | 119.0 | C33—C34—H34 | 118.5 |
C17H12N4O4 | Z = 4 |
Mr = 336.31 | F(000) = 696 |
Monoclinic, P21/c | Dx = 1.489 Mg m−3 |
a = 20.8360 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 5.2746 (1) Å | µ = 0.11 mm−1 |
c = 14.0971 (2) Å | T = 78 K |
β = 104.457 (1)° | Plate, colorless |
V = 1500.23 (4) Å3 | 0.40 × 0.25 × 0.05 mm |
Siemens CCD diffractometer | 3445 independent reflections |
Radiation source: fine-focus sealed tube | 2934 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω–scan | θmax = 27.6°, θmin = 1.0° |
Absorption correction: empirical SADABS (Sheldrick, 1996) | h = −27→20 |
Tmin = 0.975, Tmax = 1.000 | k = −6→6 |
10094 measured reflections | l = −15→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
3445 reflections | (Δ/σ)max = 0.001 |
228 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C17H12N4O4 | V = 1500.23 (4) Å3 |
Mr = 336.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.8360 (3) Å | µ = 0.11 mm−1 |
b = 5.2746 (1) Å | T = 78 K |
c = 14.0971 (2) Å | 0.40 × 0.25 × 0.05 mm |
β = 104.457 (1)° |
Siemens CCD diffractometer | 3445 independent reflections |
Absorption correction: empirical SADABS (Sheldrick, 1996) | 2934 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 1.000 | Rint = 0.048 |
10094 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.40 e Å−3 |
3445 reflections | Δρmin = −0.52 e Å−3 |
228 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.81007 (5) | 1.6028 (2) | 0.22845 (8) | 0.0218 (3) | |
O2 | 0.81247 (5) | 1.9763 (2) | 0.29337 (8) | 0.0234 (3) | |
O3 | 0.96491 (6) | 2.5705 (2) | 0.20348 (10) | 0.0318 (3) | |
O4 | 1.01989 (6) | 2.4242 (3) | 0.10337 (10) | 0.0408 (4) | |
N1 | 0.69744 (6) | 1.8705 (2) | 0.08211 (8) | 0.0146 (3) | |
N2 | 0.82012 (6) | 1.8321 (2) | 0.22873 (8) | 0.0161 (3) | |
N3 | 0.97264 (7) | 2.4211 (3) | 0.14122 (10) | 0.0254 (3) | |
N4 | 0.56525 (6) | 2.1212 (2) | 0.17702 (9) | 0.0187 (3) | |
C1 | 0.63491 (7) | 1.9080 (3) | 0.08969 (10) | 0.0143 (3) | |
C2 | 0.58149 (7) | 1.7649 (3) | 0.03705 (10) | 0.0176 (3) | |
H2 | 0.5378 | 1.7983 | 0.0426 | 0.021* | |
C3 | 0.59349 (7) | 1.5736 (3) | −0.02329 (11) | 0.0196 (3) | |
H3 | 0.5580 | 1.4724 | −0.0595 | 0.023* | |
C4 | 0.65760 (7) | 1.5307 (3) | −0.03051 (10) | 0.0178 (3) | |
H4 | 0.6670 | 1.3999 | −0.0714 | 0.021* | |
C5 | 0.70826 (7) | 1.6842 (3) | 0.02375 (10) | 0.0148 (3) | |
C6 | 0.77891 (7) | 1.6300 (3) | 0.01972 (11) | 0.0179 (3) | |
C7 | 0.82868 (7) | 1.8387 (3) | 0.05481 (10) | 0.0161 (3) | |
C8 | 0.84580 (6) | 1.9399 (3) | 0.14952 (10) | 0.0142 (3) | |
C9 | 0.89044 (7) | 2.1354 (3) | 0.17801 (10) | 0.0153 (3) | |
H9 | 0.8986 | 2.2071 | 0.2417 | 0.018* | |
C10 | 0.92269 (7) | 2.2221 (3) | 0.11014 (11) | 0.0189 (3) | |
C11 | 0.90986 (8) | 2.1284 (3) | 0.01600 (11) | 0.0255 (4) | |
H11 | 0.9334 | 2.1893 | −0.0290 | 0.031* | |
C12 | 0.86145 (7) | 1.9421 (3) | −0.01124 (11) | 0.0225 (3) | |
H12 | 0.8503 | 1.8834 | −0.0770 | 0.027* | |
C13 | 0.62558 (7) | 2.1097 (3) | 0.15857 (10) | 0.0146 (3) | |
C14 | 0.67691 (7) | 2.2751 (3) | 0.20159 (10) | 0.0165 (3) | |
H14 | 0.7189 | 2.2621 | 0.1869 | 0.020* | |
C15 | 0.66582 (7) | 2.4580 (3) | 0.26585 (11) | 0.0185 (3) | |
H15 | 0.6999 | 2.5732 | 0.2958 | 0.022* | |
C16 | 0.60399 (7) | 2.4704 (3) | 0.28583 (11) | 0.0197 (3) | |
H16 | 0.5949 | 2.5933 | 0.3300 | 0.024* | |
C17 | 0.55597 (7) | 2.2994 (3) | 0.23989 (11) | 0.0205 (3) | |
H17 | 0.5137 | 2.3090 | 0.2538 | 0.025* | |
H61 | 0.7935 | 1.4749 | 0.0555 | 0.028 (5)* | |
H62 | 0.7788 | 1.5799 | −0.0468 | 0.042 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0242 (6) | 0.0199 (5) | 0.0247 (6) | −0.0020 (4) | 0.0126 (4) | 0.0049 (4) |
O2 | 0.0306 (6) | 0.0296 (6) | 0.0143 (5) | 0.0049 (4) | 0.0138 (4) | −0.0018 (4) |
O3 | 0.0247 (6) | 0.0194 (6) | 0.0464 (8) | 0.0002 (4) | −0.0002 (5) | −0.0049 (5) |
O4 | 0.0328 (7) | 0.0639 (9) | 0.0285 (7) | −0.0261 (6) | 0.0128 (5) | 0.0033 (6) |
N1 | 0.0163 (6) | 0.0164 (5) | 0.0139 (6) | −0.0007 (4) | 0.0091 (4) | 0.0006 (4) |
N2 | 0.0158 (6) | 0.0220 (6) | 0.0130 (6) | 0.0018 (4) | 0.0086 (4) | 0.0021 (4) |
N3 | 0.0225 (7) | 0.0266 (7) | 0.0247 (7) | −0.0065 (5) | 0.0017 (5) | 0.0076 (5) |
N4 | 0.0175 (6) | 0.0199 (6) | 0.0229 (6) | 0.0010 (4) | 0.0129 (5) | 0.0003 (5) |
C1 | 0.0156 (6) | 0.0156 (6) | 0.0143 (6) | −0.0001 (5) | 0.0085 (5) | 0.0034 (5) |
C2 | 0.0157 (6) | 0.0210 (7) | 0.0180 (7) | −0.0020 (5) | 0.0081 (5) | 0.0027 (5) |
C3 | 0.0191 (7) | 0.0222 (7) | 0.0177 (7) | −0.0051 (5) | 0.0052 (5) | −0.0006 (5) |
C4 | 0.0221 (7) | 0.0180 (7) | 0.0152 (7) | −0.0028 (5) | 0.0083 (5) | −0.0011 (5) |
C5 | 0.0176 (6) | 0.0167 (6) | 0.0128 (6) | −0.0010 (5) | 0.0089 (5) | 0.0009 (5) |
C6 | 0.0188 (7) | 0.0201 (7) | 0.0183 (7) | −0.0015 (5) | 0.0110 (5) | −0.0063 (5) |
C7 | 0.0153 (6) | 0.0198 (7) | 0.0162 (7) | −0.0001 (5) | 0.0097 (5) | −0.0027 (5) |
C8 | 0.0158 (6) | 0.0178 (6) | 0.0124 (6) | 0.0024 (5) | 0.0100 (5) | 0.0023 (5) |
C9 | 0.0165 (6) | 0.0159 (6) | 0.0143 (6) | 0.0021 (5) | 0.0054 (5) | 0.0002 (5) |
C10 | 0.0167 (7) | 0.0201 (7) | 0.0202 (7) | −0.0035 (5) | 0.0052 (5) | 0.0026 (5) |
C11 | 0.0232 (8) | 0.0381 (9) | 0.0190 (7) | −0.0085 (6) | 0.0124 (6) | 0.0027 (6) |
C12 | 0.0220 (7) | 0.0354 (8) | 0.0139 (7) | −0.0057 (6) | 0.0117 (5) | −0.0042 (6) |
C13 | 0.0160 (6) | 0.0155 (6) | 0.0152 (6) | 0.0009 (5) | 0.0093 (5) | 0.0039 (5) |
C14 | 0.0173 (6) | 0.0181 (7) | 0.0171 (7) | −0.0001 (5) | 0.0100 (5) | 0.0027 (5) |
C15 | 0.0194 (7) | 0.0192 (7) | 0.0192 (7) | −0.0004 (5) | 0.0089 (5) | 0.0007 (5) |
C16 | 0.0245 (7) | 0.0196 (7) | 0.0188 (7) | 0.0038 (5) | 0.0125 (5) | −0.0003 (5) |
C17 | 0.0193 (7) | 0.0220 (7) | 0.0252 (8) | 0.0024 (5) | 0.0151 (5) | 0.0013 (6) |
O1—N2 | 1.2275 (16) | C6—H61 | 0.9691 |
O2—N2 | 1.2276 (16) | C6—H62 | 0.9736 |
O3—N3 | 1.2197 (19) | C7—C12 | 1.3956 (19) |
O4—N3 | 1.231 (2) | C7—C8 | 1.3989 (19) |
N1—C5 | 1.3363 (17) | C8—C9 | 1.3793 (19) |
N1—C1 | 1.3482 (17) | C9—C10 | 1.3775 (19) |
N2—C8 | 1.4680 (16) | C9—H9 | 0.9500 |
N3—C10 | 1.4660 (18) | C10—C11 | 1.378 (2) |
N4—C17 | 1.3386 (19) | C11—C12 | 1.392 (2) |
N4—C13 | 1.3471 (18) | C11—H11 | 0.9500 |
C1—C2 | 1.3953 (19) | C12—H12 | 0.9500 |
C1—C13 | 1.485 (2) | C13—C14 | 1.3962 (19) |
C2—C3 | 1.382 (2) | C14—C15 | 1.3819 (19) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.383 (2) | C15—C16 | 1.387 (2) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.3971 (18) | C16—C17 | 1.382 (2) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.5145 (19) | C17—H17 | 0.9500 |
C6—C7 | 1.5086 (19) | ||
C5—N1—C1 | 118.13 (12) | C8—C7—C6 | 125.59 (13) |
O1—N2—O2 | 124.01 (12) | C9—C8—C7 | 123.77 (13) |
O1—N2—C8 | 118.27 (11) | C9—C8—N2 | 114.54 (12) |
O2—N2—C8 | 117.66 (12) | C7—C8—N2 | 121.58 (12) |
O3—N3—O4 | 124.52 (14) | C10—C9—C8 | 117.15 (12) |
O3—N3—C10 | 117.78 (14) | C10—C9—H9 | 121.4 |
O4—N3—C10 | 117.70 (14) | C8—C9—H9 | 121.4 |
C17—N4—C13 | 117.11 (12) | C9—C10—C11 | 122.59 (13) |
N1—C1—C2 | 122.48 (13) | C9—C10—N3 | 117.60 (13) |
N1—C1—C13 | 116.34 (12) | C11—C10—N3 | 119.81 (13) |
C2—C1—C13 | 121.18 (13) | C10—C11—C12 | 118.15 (14) |
C3—C2—C1 | 118.65 (13) | C10—C11—H11 | 120.9 |
C3—C2—H2 | 120.7 | C12—C11—H11 | 120.9 |
C1—C2—H2 | 120.7 | C11—C12—C7 | 122.24 (13) |
C2—C3—C4 | 119.40 (13) | C11—C12—H12 | 118.9 |
C2—C3—H3 | 120.3 | C7—C12—H12 | 118.9 |
C4—C3—H3 | 120.3 | N4—C13—C14 | 122.57 (13) |
C3—C4—C5 | 118.45 (13) | N4—C13—C1 | 116.07 (12) |
C3—C4—H4 | 120.8 | C14—C13—C1 | 121.36 (12) |
C5—C4—H4 | 120.8 | C15—C14—C13 | 119.06 (13) |
N1—C5—C4 | 122.87 (13) | C15—C14—H14 | 120.5 |
N1—C5—C6 | 118.47 (12) | C13—C14—H14 | 120.5 |
C4—C5—C6 | 118.60 (12) | C14—C15—C16 | 118.80 (13) |
C7—C6—C5 | 116.42 (11) | C14—C15—H15 | 120.6 |
C7—C6—H61 | 110.2 | C16—C15—H15 | 120.6 |
C5—C6—H61 | 108.7 | C17—C16—C15 | 118.33 (13) |
C7—C6—H62 | 110.5 | C17—C16—H16 | 120.8 |
C5—C6—H62 | 108.5 | C15—C16—H16 | 120.8 |
H61—C6—H62 | 101.4 | N4—C17—C16 | 124.12 (13) |
C12—C7—C8 | 115.90 (13) | N4—C17—H17 | 117.9 |
C12—C7—C6 | 118.51 (12) | C16—C17—H17 | 117.9 |
Experimental details
(alpha) | (gamma) | |
Crystal data | ||
Chemical formula | C17H12N4O4 | C17H12N4O4 |
Mr | 336.31 | 336.31 |
Crystal system, space group | Orthorhombic, Pna21 | Monoclinic, P21/c |
Temperature (K) | 78 | 78 |
a, b, c (Å) | 14.0059 (1), 5.1399 (1), 41.9853 (6) | 20.8360 (3), 5.2746 (1), 14.0971 (2) |
α, β, γ (°) | 90, 90, 90 | 90, 104.457 (1), 90 |
V (Å3) | 3022.48 (8) | 1500.23 (4) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.11 |
Crystal size (mm) | 0.35 × 0.10 × 0.05 | 0.40 × 0.25 × 0.05 |
Data collection | ||
Diffractometer | Siemens CCD diffractometer | Siemens CCD diffractometer |
Absorption correction | Empirical SADABS (Sheldrick, 1996) | Empirical SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.674, 1.000 | 0.975, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19857, 6678, 4589 | 10094, 3445, 2934 |
Rint | 0.080 | 0.048 |
(sin θ/λ)max (Å−1) | 0.649 | 0.652 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.179, 1.03 | 0.049, 0.153, 1.11 |
No. of reflections | 6678 | 3445 |
No. of parameters | 452 | 228 |
No. of restraints | 1 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.13, −0.27 | 0.40, −0.52 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | −1.0 (19) | ? |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-II (Johnson, 1976).