Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009736/ob6494sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009736/ob6494Isup2.hkl |
CCDC reference: 270505
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.126
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. O1 .. 2.61 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.71 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O4 .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O4 .. 2.92 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: TEXSAN (Molecular Structure Corporation, 1999); software used to prepare material for publication: SHELXTL.
C18H14N2O4 | Dx = 1.385 Mg m−3 |
Mr = 322.31 | Melting point: 513-514 K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8710 (4) Å | Cell parameters from 3502 reflections |
b = 21.440 (2) Å | θ = 2.2–28.1° |
c = 18.7091 (19) Å | µ = 0.10 mm−1 |
β = 95.555 (2)° | T = 183 K |
V = 1545.4 (3) Å3 | Needle, yellow |
Z = 4 | 0.30 × 0.25 × 0.02 mm |
F(000) = 672 |
Bruker SMART CCD area-detector diffractometer | 3490 independent reflections |
Radiation source: rotating anode | 2640 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.366 pixels mm-1 | θmax = 28.2°, θmin = 1.5° |
φ and ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −28→20 |
Tmin = 0.909, Tmax = 0.998 | l = −22→23 |
9325 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0743P)2 + 0.088P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
3490 reflections | Δρmax = 0.24 e Å−3 |
218 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0075 (15) |
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 | ||
C1 | 1.3424 (3) | 0.59348 (6) | 0.59861 (8) | 0.0368 (3) | |
C2 | 1.2112 (4) | 0.57741 (7) | 0.52994 (8) | 0.0411 (3) | |
H2 | 1.2433 | 0.5365 | 0.5122 | 0.049* | |
C3 | 1.0328 (4) | 0.62165 (6) | 0.48752 (8) | 0.0383 (3) | |
H3 | 0.9380 | 0.6107 | 0.4404 | 0.046* | |
C4 | 0.9889 (3) | 0.68226 (6) | 0.51257 (7) | 0.0312 (3) | |
C5 | 1.1238 (3) | 0.69624 (6) | 0.58283 (7) | 0.0351 (3) | |
H5 | 1.0933 | 0.7370 | 0.6010 | 0.042* | |
C6 | 1.2997 (3) | 0.65251 (6) | 0.62640 (7) | 0.0376 (3) | |
H6 | 1.3889 | 0.6626 | 0.6741 | 0.045* | |
C7 | 0.8069 (3) | 0.72819 (6) | 0.46529 (7) | 0.0342 (3) | |
H7 | 0.6665 | 0.7127 | 0.4247 | 0.041* | |
C8 | 0.8196 (3) | 0.79021 (6) | 0.47386 (7) | 0.0351 (3) | |
H8 | 0.9540 | 0.8061 | 0.5151 | 0.042* | |
C9 | 0.6449 (3) | 0.83450 (7) | 0.42533 (7) | 0.0366 (3) | |
H9 | 0.5023 | 0.8192 | 0.3850 | 0.044* | |
C10 | 0.6736 (3) | 0.89643 (6) | 0.43431 (7) | 0.0364 (3) | |
H10 | 0.8143 | 0.9109 | 0.4754 | 0.044* | |
C11 | 0.5088 (3) | 0.94263 (6) | 0.38688 (7) | 0.0356 (3) | |
H11 | 0.3669 | 0.9289 | 0.3456 | 0.043* | |
C12 | 0.5458 (3) | 1.00413 (6) | 0.39816 (7) | 0.0348 (3) | |
H12 | 0.6851 | 1.0162 | 0.4405 | 0.042* | |
C13 | 0.3969 (3) | 1.05453 (6) | 0.35289 (7) | 0.0309 (3) | |
C14 | 0.1893 (3) | 1.04421 (6) | 0.28848 (7) | 0.0335 (3) | |
H14 | 0.1388 | 1.0026 | 0.2733 | 0.040* | |
C15 | 0.0565 (3) | 1.09322 (6) | 0.24656 (7) | 0.0346 (3) | |
H15 | −0.0838 | 1.0857 | 0.2029 | 0.042* | |
C16 | 0.1322 (3) | 1.15352 (6) | 0.26948 (7) | 0.0330 (3) | |
C17 | 0.3357 (3) | 1.16595 (6) | 0.33257 (7) | 0.0346 (3) | |
H17 | 0.3859 | 1.2077 | 0.3472 | 0.042* | |
C18 | 0.4648 (3) | 1.11635 (6) | 0.37400 (7) | 0.0338 (3) | |
H18 | 0.6029 | 1.1243 | 0.4178 | 0.041* | |
N1 | 1.5364 (3) | 0.54706 (6) | 0.64365 (8) | 0.0488 (3) | |
N2 | −0.0165 (3) | 1.20575 (6) | 0.22655 (6) | 0.0422 (3) | |
O1 | 1.5715 (4) | 0.49480 (6) | 0.61881 (8) | 0.0742 (4) | |
O2 | 1.6594 (3) | 0.56252 (6) | 0.70385 (7) | 0.0640 (4) | |
O3 | −0.2134 (3) | 1.19414 (6) | 0.17311 (6) | 0.0576 (3) | |
O4 | 0.0580 (4) | 1.25883 (5) | 0.24665 (7) | 0.0678 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0332 (6) | 0.0355 (7) | 0.0426 (8) | 0.0036 (5) | 0.0078 (6) | 0.0109 (6) |
C2 | 0.0471 (8) | 0.0300 (7) | 0.0470 (8) | 0.0017 (6) | 0.0094 (6) | 0.0010 (6) |
C3 | 0.0423 (7) | 0.0356 (7) | 0.0368 (7) | −0.0023 (6) | 0.0033 (6) | −0.0020 (6) |
C4 | 0.0262 (6) | 0.0329 (7) | 0.0347 (7) | −0.0017 (5) | 0.0038 (5) | 0.0021 (5) |
C5 | 0.0339 (6) | 0.0331 (7) | 0.0378 (7) | 0.0021 (5) | 0.0004 (5) | −0.0014 (5) |
C6 | 0.0362 (7) | 0.0410 (8) | 0.0349 (7) | 0.0011 (6) | 0.0006 (5) | 0.0031 (6) |
C7 | 0.0296 (6) | 0.0392 (8) | 0.0331 (7) | −0.0001 (5) | −0.0009 (5) | 0.0003 (5) |
C8 | 0.0298 (6) | 0.0382 (7) | 0.0366 (7) | −0.0002 (5) | 0.0002 (5) | 0.0031 (6) |
C9 | 0.0317 (6) | 0.0418 (8) | 0.0360 (7) | 0.0021 (6) | 0.0011 (5) | 0.0044 (6) |
C10 | 0.0324 (6) | 0.0392 (8) | 0.0373 (7) | 0.0012 (5) | 0.0015 (5) | 0.0051 (6) |
C11 | 0.0316 (6) | 0.0402 (8) | 0.0349 (7) | 0.0008 (6) | 0.0024 (5) | 0.0036 (6) |
C12 | 0.0302 (6) | 0.0399 (8) | 0.0336 (7) | −0.0014 (5) | −0.0002 (5) | 0.0021 (5) |
C13 | 0.0254 (5) | 0.0366 (7) | 0.0310 (6) | 0.0007 (5) | 0.0038 (5) | 0.0018 (5) |
C14 | 0.0333 (6) | 0.0344 (7) | 0.0326 (7) | −0.0011 (5) | 0.0027 (5) | −0.0032 (5) |
C15 | 0.0331 (6) | 0.0440 (8) | 0.0262 (6) | 0.0002 (6) | 0.0006 (5) | −0.0018 (5) |
C16 | 0.0319 (6) | 0.0370 (7) | 0.0308 (6) | 0.0043 (5) | 0.0057 (5) | 0.0048 (5) |
C17 | 0.0329 (6) | 0.0331 (7) | 0.0378 (7) | −0.0025 (5) | 0.0038 (5) | −0.0017 (5) |
C18 | 0.0306 (6) | 0.0380 (7) | 0.0319 (6) | −0.0020 (5) | −0.0011 (5) | −0.0018 (5) |
N1 | 0.0472 (7) | 0.0461 (8) | 0.0546 (9) | 0.0099 (6) | 0.0122 (6) | 0.0195 (6) |
N2 | 0.0456 (7) | 0.0441 (7) | 0.0374 (7) | 0.0088 (5) | 0.0070 (5) | 0.0073 (5) |
O1 | 0.1054 (11) | 0.0459 (7) | 0.0723 (9) | 0.0311 (7) | 0.0135 (8) | 0.0148 (6) |
O2 | 0.0669 (8) | 0.0649 (8) | 0.0577 (8) | 0.0122 (6) | −0.0070 (6) | 0.0217 (6) |
O3 | 0.0610 (7) | 0.0662 (8) | 0.0425 (6) | 0.0087 (6) | −0.0101 (5) | 0.0134 (5) |
O4 | 0.0983 (10) | 0.0381 (7) | 0.0641 (8) | 0.0119 (6) | −0.0067 (7) | 0.0049 (5) |
C1—C2 | 1.379 (2) | C11—C12 | 1.341 (2) |
C1—C6 | 1.384 (2) | C11—H11 | 0.950 |
C1—N1 | 1.463 (2) | C12—C13 | 1.457 (2) |
C2—C3 | 1.379 (2) | C12—H12 | 0.950 |
C2—H2 | 0.950 | C13—C14 | 1.400 (2) |
C3—C4 | 1.398 (2) | C13—C18 | 1.401 (2) |
C3—H3 | 0.950 | C14—C15 | 1.381 (2) |
C4—C5 | 1.399 (2) | C14—H14 | 0.950 |
C4—C7 | 1.459 (2) | C15—C16 | 1.384 (2) |
C5—C6 | 1.378 (2) | C15—H15 | 0.950 |
C5—H5 | 0.950 | C16—C17 | 1.381 (2) |
C6—H6 | 0.950 | C16—N2 | 1.463 (2) |
C7—C8 | 1.340 (2) | C17—C18 | 1.381 (2) |
C7—H7 | 0.950 | C17—H17 | 0.950 |
C8—C9 | 1.437 (2) | C18—H18 | 0.950 |
C8—H8 | 0.950 | N1—O2 | 1.225 (2) |
C9—C10 | 1.342 (2) | N1—O1 | 1.226 (2) |
C9—H9 | 0.950 | N2—O3 | 1.223 (2) |
C10—C11 | 1.437 (2) | N2—O4 | 1.224 (2) |
C10—H10 | 0.950 | ||
C2—C1—C6 | 122.1 (1) | C12—C11—C10 | 123.1 (1) |
C2—C1—N1 | 119.3 (1) | C12—C11—H11 | 118.4 |
C6—C1—N1 | 118.6 (1) | C10—C11—H11 | 118.4 |
C3—C2—C1 | 118.9 (1) | C11—C12—C13 | 127.4 (1) |
C3—C2—H2 | 120.5 | C11—C12—H12 | 116.3 |
C1—C2—H2 | 120.5 | C13—C12—H12 | 116.3 |
C2—C3—C4 | 121.2 (1) | C14—C13—C18 | 118.0 (1) |
C2—C3—H3 | 119.4 | C14—C13—C12 | 123.0 (1) |
C4—C3—H3 | 119.4 | C18—C13—C12 | 119.0 (1) |
C3—C4—C5 | 117.9 (1) | C15—C14—C13 | 121.3 (1) |
C3—C4—C7 | 119.5 (1) | C15—C14—H14 | 119.3 |
C5—C4—C7 | 122.7 (1) | C13—C14—H14 | 119.3 |
C6—C5—C4 | 121.9 (1) | C14—C15—C16 | 118.6 (1) |
C6—C5—H5 | 119.1 | C14—C15—H15 | 120.7 |
C4—C5—H5 | 119.1 | C16—C15—H15 | 120.7 |
C5—C6—C1 | 118.0 (1) | C17—C16—C15 | 122.1 (1) |
C5—C6—H6 | 121.0 | C17—C16—N2 | 118.9 (1) |
C1—C6—H6 | 121.0 | C15—C16—N2 | 119.0 (1) |
C8—C7—C4 | 126.0 (1) | C16—C17—C18 | 118.5 (1) |
C8—C7—H7 | 117.0 | C16—C17—H17 | 120.8 |
C4—C7—H7 | 117.0 | C18—C17—H17 | 120.8 |
C7—C8—C9 | 124.8 (1) | C17—C18—C13 | 121.5 (1) |
C7—C8—H8 | 117.6 | C17—C18—H18 | 119.2 |
C9—C8—H8 | 117.6 | C13—C18—H18 | 119.2 |
C10—C9—C8 | 123.2 (1) | O2—N1—O1 | 123.3 (1) |
C10—C9—H9 | 118.4 | O2—N1—C1 | 118.5 (1) |
C8—C9—H9 | 118.4 | O1—N1—C1 | 118.2 (1) |
C9—C10—C11 | 125.3 (1) | O3—N2—O4 | 123.4 (1) |
C9—C10—H10 | 117.3 | O3—N2—C16 | 118.3 (1) |
C11—C10—H10 | 117.3 | O4—N2—C16 | 118.3 (1) |
C6—C1—C2—C3 | 0.2 (2) | C18—C13—C14—C15 | 0.4 (2) |
N1—C1—C2—C3 | −179.2 (1) | C12—C13—C14—C15 | −179.2 (1) |
C1—C2—C3—C4 | 1.1 (2) | C13—C14—C15—C16 | −0.1 (2) |
C2—C3—C4—C5 | −1.7 (2) | C14—C15—C16—C17 | 0.1 (2) |
C2—C3—C4—C7 | 178.3 (1) | C14—C15—C16—N2 | −178.1 (1) |
C3—C4—C5—C6 | 1.0 (2) | C15—C16—C17—C18 | −0.4 (2) |
C7—C4—C5—C6 | −179.0 (1) | N2—C16—C17—C18 | 177.8 (1) |
C4—C5—C6—C1 | 0.3 (2) | C16—C17—C18—C13 | 0.8 (2) |
C2—C1—C6—C5 | −0.9 (2) | C14—C13—C18—C17 | −0.7 (2) |
N1—C1—C6—C5 | 178.5 (1) | C12—C13—C18—C17 | 178.8 (1) |
C3—C4—C7—C8 | −162.0 (1) | C2—C1—N1—O2 | 178.1 (1) |
C5—C4—C7—C8 | 18.0 (2) | C6—C1—N1—O2 | −1.4 (2) |
C4—C7—C8—C9 | 178.2 (1) | C2—C1—N1—O1 | −1.0 (2) |
C7—C8—C9—C10 | −177.5 (1) | C6—C1—N1—O1 | 179.6 (1) |
C8—C9—C10—C11 | 179.0 (1) | C17—C16—N2—O3 | −175.6 (1) |
C9—C10—C11—C12 | −179.9 (1) | C15—C16—N2—O3 | 2.7 (2) |
C10—C11—C12—C13 | 178.6 (1) | C17—C16—N2—O4 | 3.2 (2) |
C11—C12—C13—C14 | −0.7 (2) | C15—C16—N2—O4 | −178.6 (1) |
C11—C12—C13—C18 | 179.8 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O3i | 0.95 | 2.44 | 3.371 (2) | 166 |
C14—H14···O2ii | 0.95 | 2.57 | 3.366 (2) | 141 |
C15—H15···O1ii | 0.95 | 2.61 | 3.454 (2) | 148 |
C2—H2···O1iii | 0.95 | 2.71 | 3.364 (2) | 127 |
C5—H5···O4iv | 0.95 | 2.97 | 3.470 (2) | 115 |
C6—H6···O4iv | 0.95 | 2.92 | 3.437 (2) | 115 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−2, −y+3/2, z−1/2; (iii) −x+3, −y+1, −z+1; (iv) −x+1, −y+2, −z+1. |
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