Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014661/cv6204sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014661/cv6204Isup2.hkl |
CCDC reference: 221678
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.096
- Data-to-parameter ratio = 6.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N1 - H1 ... ? General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 1730 Count of symmetry unique reflns 1733 Completeness (_total/calc) 99.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C22H20N2O3 | Dx = 1.296 Mg m−3 |
Mr = 360.40 | Melting point: 401 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9941 (2) Å | Cell parameters from 1904 reflections |
b = 19.8913 (4) Å | θ = 2.0–25.0° |
c = 10.3244 (2) Å | µ = 0.09 mm−1 |
V = 1847.08 (7) Å3 | T = 160 K |
Z = 4 | Prism, colourless |
F(000) = 760 | 0.30 × 0.18 × 0.10 mm |
Nonius KappaCCD diffractometer | 1538 reflections with I > 2σ(I) |
Radiation source: Nonius FR591 sealed tube generator | Rint = 0.065 |
Horizontally mounted graphite crystal monochromator | θmax = 25.0°, θmin = 2.5° |
Detector resolution: 9 pixels mm-1 | h = −10→10 |
φ and ω scans with κ offsets | k = −23→23 |
24574 measured reflections | l = −12→12 |
1730 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom & difmap |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.2477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1728 reflections | Δρmax = 0.14 e Å−3 |
249 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.034 (5) |
Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.908 (1) Frames collected: 856 Seconds exposure per frame: 75 Degrees rotation per frame: 0.5 Crystal-Detector distance (mm): 30.0 |
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 | ||
O5 | 0.9796 (2) | 0.26276 (9) | 0.8438 (2) | 0.0477 (5) | |
O8 | 0.8531 (2) | 0.37184 (10) | 0.5655 (2) | 0.0519 (6) | |
O10 | 0.7606 (2) | 0.36455 (11) | 0.8948 (2) | 0.0543 (6) | |
N1 | 0.8132 (2) | 0.12648 (11) | 0.5617 (2) | 0.0355 (5) | |
H1 | 0.853 (3) | 0.0939 (16) | 0.503 (4) | 0.050 (8)* | |
N4 | 0.8088 (2) | 0.27632 (10) | 0.6832 (2) | 0.0384 (5) | |
C2 | 0.8124 (3) | 0.19199 (12) | 0.4973 (3) | 0.0348 (6) | |
H2 | 0.9173 | 0.2078 | 0.4871 | 0.042* | |
C3 | 0.7255 (3) | 0.24395 (13) | 0.5771 (3) | 0.0386 (6) | |
H31 | 0.6894 | 0.2795 | 0.5177 | 0.046* | |
H32 | 0.6371 | 0.2215 | 0.6145 | 0.046* | |
C5 | 0.8805 (3) | 0.23864 (13) | 0.7782 (3) | 0.0390 (6) | |
C6 | 0.8349 (3) | 0.16612 (13) | 0.7890 (3) | 0.0413 (6) | |
H61 | 0.7251 | 0.1631 | 0.7848 | 0.050* | |
H62 | 0.8669 | 0.1484 | 0.8741 | 0.050* | |
C7 | 0.9022 (3) | 0.12241 (13) | 0.6812 (3) | 0.0348 (6) | |
H7 | 1.0046 | 0.1393 | 0.6621 | 0.042* | |
C8 | 0.8375 (3) | 0.34583 (13) | 0.6712 (3) | 0.0399 (6) | |
C9 | 0.8363 (3) | 0.38553 (14) | 0.7894 (3) | 0.0409 (6) | |
C11 | 0.7730 (4) | 0.4162 (2) | 0.9835 (3) | 0.0665 (10) | |
H11 | 0.7288 | 0.4160 | 1.0671 | 0.080* | |
C12 | 0.8536 (5) | 0.46537 (17) | 0.9373 (4) | 0.0719 (11) | |
H12 | 0.8798 | 0.5057 | 0.9810 | 0.086* | |
C13 | 0.8947 (4) | 0.44694 (14) | 0.8091 (4) | 0.0547 (8) | |
H13 | 0.9516 | 0.4727 | 0.7495 | 0.066* | |
C14 | 0.7424 (3) | 0.18561 (12) | 0.3647 (3) | 0.0361 (6) | |
C15 | 0.7968 (4) | 0.22333 (14) | 0.2625 (3) | 0.0478 (7) | |
H15 | 0.8785 | 0.2528 | 0.2761 | 0.057* | |
C16 | 0.7331 (4) | 0.21858 (16) | 0.1398 (3) | 0.0563 (9) | |
H16 | 0.7712 | 0.2448 | 0.0705 | 0.068* | |
C17 | 0.6141 (4) | 0.17559 (15) | 0.1189 (3) | 0.0519 (8) | |
H17 | 0.5714 | 0.1718 | 0.0350 | 0.062* | |
C18 | 0.5584 (3) | 0.13852 (15) | 0.2199 (3) | 0.0463 (7) | |
H18 | 0.4767 | 0.1092 | 0.2058 | 0.056* | |
C19 | 0.6206 (3) | 0.14345 (14) | 0.3428 (3) | 0.0407 (6) | |
H19 | 0.5801 | 0.1180 | 0.4122 | 0.049* | |
C20 | 0.9130 (3) | 0.04858 (13) | 0.7207 (3) | 0.0382 (6) | |
C21 | 1.0312 (3) | 0.01038 (13) | 0.6776 (3) | 0.0437 (6) | |
H21 | 1.1060 | 0.0305 | 0.6255 | 0.052* | |
C22 | 1.0417 (3) | −0.05721 (14) | 0.7099 (4) | 0.0547 (8) | |
H22 | 1.1235 | −0.0830 | 0.6797 | 0.066* | |
C23 | 0.9340 (4) | −0.08695 (15) | 0.7854 (4) | 0.0558 (8) | |
H23 | 0.9413 | −0.1332 | 0.8074 | 0.067* | |
C24 | 0.8156 (4) | −0.04912 (16) | 0.8288 (3) | 0.0546 (8) | |
H24 | 0.7410 | −0.0694 | 0.8809 | 0.066* | |
C25 | 0.8048 (3) | 0.01822 (15) | 0.7970 (3) | 0.0486 (7) | |
H25 | 0.7229 | 0.0439 | 0.8274 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O5 | 0.0533 (11) | 0.0496 (10) | 0.0403 (11) | 0.0049 (9) | −0.0099 (10) | −0.0068 (10) |
O8 | 0.0660 (13) | 0.0549 (12) | 0.0347 (12) | 0.0078 (10) | 0.0038 (11) | 0.0043 (10) |
O10 | 0.0588 (12) | 0.0642 (13) | 0.0399 (13) | 0.0016 (10) | 0.0034 (10) | −0.0047 (11) |
N1 | 0.0402 (11) | 0.0386 (11) | 0.0277 (12) | 0.0031 (9) | −0.0001 (10) | 0.0002 (10) |
N4 | 0.0440 (11) | 0.0402 (11) | 0.0309 (12) | 0.0047 (9) | −0.0037 (10) | −0.0045 (10) |
C2 | 0.0382 (13) | 0.0360 (13) | 0.0303 (14) | 0.0032 (11) | 0.0005 (11) | −0.0003 (11) |
C3 | 0.0378 (13) | 0.0447 (14) | 0.0333 (14) | 0.0074 (11) | −0.0038 (11) | −0.0056 (12) |
C5 | 0.0447 (14) | 0.0457 (15) | 0.0267 (13) | 0.0065 (12) | −0.0002 (13) | −0.0035 (12) |
C6 | 0.0466 (15) | 0.0462 (15) | 0.0311 (14) | 0.0013 (12) | −0.0009 (12) | −0.0011 (13) |
C7 | 0.0345 (12) | 0.0401 (13) | 0.0299 (13) | −0.0005 (10) | 0.0000 (12) | 0.0005 (11) |
C8 | 0.0391 (13) | 0.0446 (14) | 0.0361 (16) | 0.0095 (11) | 0.0010 (13) | −0.0017 (13) |
C9 | 0.0446 (15) | 0.0464 (15) | 0.0318 (14) | 0.0090 (12) | −0.0025 (12) | −0.0007 (13) |
C11 | 0.075 (2) | 0.086 (3) | 0.0388 (18) | 0.026 (2) | −0.0037 (17) | −0.0233 (19) |
C12 | 0.104 (3) | 0.0423 (17) | 0.070 (2) | 0.0122 (19) | −0.028 (2) | −0.0179 (18) |
C13 | 0.0660 (19) | 0.0416 (15) | 0.057 (2) | −0.0065 (14) | −0.0106 (16) | 0.0040 (15) |
C14 | 0.0429 (13) | 0.0341 (13) | 0.0314 (14) | 0.0079 (11) | 0.0016 (11) | 0.0001 (11) |
C15 | 0.0701 (19) | 0.0398 (14) | 0.0334 (16) | −0.0074 (13) | 0.0051 (14) | 0.0016 (12) |
C16 | 0.091 (2) | 0.0456 (16) | 0.0320 (16) | −0.0003 (16) | 0.0019 (16) | 0.0074 (13) |
C17 | 0.073 (2) | 0.0525 (16) | 0.0306 (15) | 0.0164 (15) | −0.0078 (15) | −0.0029 (13) |
C18 | 0.0498 (16) | 0.0507 (16) | 0.0383 (17) | 0.0050 (13) | −0.0064 (13) | −0.0033 (13) |
C19 | 0.0418 (14) | 0.0463 (14) | 0.0341 (15) | 0.0025 (12) | −0.0012 (12) | 0.0023 (12) |
C20 | 0.0385 (13) | 0.0450 (15) | 0.0310 (14) | −0.0044 (11) | −0.0060 (11) | 0.0025 (11) |
C21 | 0.0388 (14) | 0.0453 (14) | 0.0468 (16) | −0.0016 (11) | −0.0030 (14) | 0.0041 (13) |
C22 | 0.0499 (15) | 0.0441 (15) | 0.070 (2) | 0.0014 (13) | −0.0106 (16) | 0.0085 (16) |
C23 | 0.0624 (18) | 0.0464 (16) | 0.0584 (19) | −0.0053 (14) | −0.0179 (17) | 0.0146 (16) |
C24 | 0.0643 (18) | 0.0612 (19) | 0.0383 (17) | −0.0191 (16) | −0.0047 (15) | 0.0124 (15) |
C25 | 0.0498 (16) | 0.0524 (16) | 0.0435 (17) | −0.0065 (13) | 0.0015 (14) | 0.0056 (14) |
O5—C5 | 1.218 (3) | C12—C13 | 1.423 (6) |
O8—C8 | 1.216 (4) | C12—H12 | 0.9500 |
O10—C9 | 1.350 (4) | C13—H13 | 0.9500 |
O10—C11 | 1.382 (4) | C14—C15 | 1.384 (4) |
N1—C2 | 1.463 (3) | C14—C19 | 1.398 (4) |
N1—C7 | 1.474 (3) | C15—C16 | 1.393 (5) |
N1—H1 | 0.96 (3) | C15—H15 | 0.9500 |
N4—C5 | 1.393 (4) | C16—C17 | 1.387 (5) |
N4—C8 | 1.412 (3) | C16—H16 | 0.9500 |
N4—C3 | 1.475 (3) | C17—C18 | 1.372 (5) |
C2—C14 | 1.512 (4) | C17—H17 | 0.9500 |
C2—C3 | 1.536 (4) | C18—C19 | 1.389 (4) |
C2—H2 | 1.0000 | C18—H18 | 0.9500 |
C3—H31 | 0.9900 | C19—H19 | 0.9500 |
C3—H32 | 0.9900 | C20—C21 | 1.380 (4) |
C5—C6 | 1.504 (4) | C20—C25 | 1.390 (4) |
C6—C7 | 1.536 (4) | C21—C22 | 1.388 (4) |
C6—H61 | 0.9900 | C21—H21 | 0.9500 |
C6—H62 | 0.9900 | C22—C23 | 1.377 (5) |
C7—C20 | 1.527 (4) | C22—H22 | 0.9500 |
C7—H7 | 1.0000 | C23—C24 | 1.379 (5) |
C8—C9 | 1.454 (4) | C23—H23 | 0.9500 |
C9—C13 | 1.345 (4) | C24—C25 | 1.383 (4) |
C11—C12 | 1.307 (6) | C24—H24 | 0.9500 |
C11—H11 | 0.9500 | C25—H25 | 0.9500 |
C9—O10—C11 | 105.3 (3) | C11—C12—C13 | 106.9 (3) |
C2—N1—C7 | 115.6 (2) | C11—C12—H12 | 126.5 |
C2—N1—H1 | 108.5 (19) | C13—C12—H12 | 126.5 |
C7—N1—H1 | 106.9 (19) | C9—C13—C12 | 105.8 (3) |
C5—N4—C8 | 120.3 (2) | C9—C13—H13 | 127.1 |
C5—N4—C3 | 121.6 (2) | C12—C13—H13 | 127.1 |
C8—N4—C3 | 117.1 (2) | C15—C14—C19 | 118.6 (3) |
N1—C2—C14 | 109.8 (2) | C15—C14—C2 | 119.8 (2) |
N1—C2—C3 | 111.0 (2) | C19—C14—C2 | 121.5 (3) |
C14—C2—C3 | 109.3 (2) | C14—C15—C16 | 120.7 (3) |
N1—C2—H2 | 108.9 | C14—C15—H15 | 119.6 |
C14—C2—H2 | 108.9 | C16—C15—H15 | 119.6 |
C3—C2—H2 | 108.9 | C17—C16—C15 | 120.1 (3) |
N4—C3—C2 | 115.7 (2) | C17—C16—H16 | 120.0 |
N4—C3—H31 | 108.4 | C15—C16—H16 | 120.0 |
C2—C3—H31 | 108.4 | C18—C17—C16 | 119.6 (3) |
N4—C3—H32 | 108.4 | C18—C17—H17 | 120.2 |
C2—C3—H32 | 108.4 | C16—C17—H17 | 120.2 |
H31—C3—H32 | 107.4 | C17—C18—C19 | 120.6 (3) |
O5—C5—N4 | 121.2 (2) | C17—C18—H18 | 119.7 |
O5—C5—C6 | 122.4 (3) | C19—C18—H18 | 119.7 |
N4—C5—C6 | 116.2 (2) | C18—C19—C14 | 120.4 (3) |
C5—C6—C7 | 112.5 (2) | C18—C19—H19 | 119.8 |
C5—C6—H61 | 109.1 | C14—C19—H19 | 119.8 |
C7—C6—H61 | 109.1 | C21—C20—C25 | 118.8 (3) |
C5—C6—H62 | 109.1 | C21—C20—C7 | 119.5 (2) |
C7—C6—H62 | 109.1 | C25—C20—C7 | 121.6 (2) |
H61—C6—H62 | 107.8 | C20—C21—C22 | 120.6 (3) |
N1—C7—C20 | 108.1 (2) | C20—C21—H21 | 119.7 |
N1—C7—C6 | 111.2 (2) | C22—C21—H21 | 119.7 |
C20—C7—C6 | 112.1 (2) | C23—C22—C21 | 120.3 (3) |
N1—C7—H7 | 108.5 | C23—C22—H22 | 119.9 |
C20—C7—H7 | 108.5 | C21—C22—H22 | 119.9 |
C6—C7—H7 | 108.5 | C22—C23—C24 | 119.5 (3) |
O8—C8—N4 | 121.1 (3) | C22—C23—H23 | 120.2 |
O8—C8—C9 | 121.6 (2) | C24—C23—H23 | 120.2 |
N4—C8—C9 | 117.2 (3) | C23—C24—C25 | 120.4 (3) |
C13—C9—O10 | 110.9 (3) | C23—C24—H24 | 119.8 |
C13—C9—C8 | 128.1 (3) | C25—C24—H24 | 119.8 |
O10—C9—C8 | 120.8 (2) | C24—C25—C20 | 120.4 (3) |
C12—C11—O10 | 111.0 (3) | C24—C25—H25 | 119.8 |
C12—C11—H11 | 124.5 | C20—C25—H25 | 119.8 |
O10—C11—H11 | 124.5 | ||
C7—N1—C2—C14 | 169.3 (2) | O10—C9—C13—C12 | 0.7 (3) |
C7—N1—C2—C3 | −69.8 (3) | C8—C9—C13—C12 | 175.6 (3) |
C5—N4—C3—C2 | −54.4 (3) | C11—C12—C13—C9 | −1.5 (4) |
C8—N4—C3—C2 | 113.6 (3) | N1—C2—C14—C15 | −143.8 (2) |
N1—C2—C3—N4 | 82.7 (3) | C3—C2—C14—C15 | 94.2 (3) |
C14—C2—C3—N4 | −156.0 (2) | N1—C2—C14—C19 | 37.7 (3) |
C8—N4—C5—O5 | −7.6 (4) | C3—C2—C14—C19 | −84.2 (3) |
C3—N4—C5—O5 | 160.1 (3) | C19—C14—C15—C16 | −1.0 (4) |
C8—N4—C5—C6 | 176.1 (2) | C2—C14—C15—C16 | −179.5 (3) |
C3—N4—C5—C6 | −16.3 (4) | C14—C15—C16—C17 | −0.2 (5) |
O5—C5—C6—C7 | −99.7 (3) | C15—C16—C17—C18 | 0.8 (5) |
N4—C5—C6—C7 | 76.6 (3) | C16—C17—C18—C19 | −0.3 (5) |
C2—N1—C7—C20 | −169.9 (2) | C17—C18—C19—C14 | −1.0 (4) |
C2—N1—C7—C6 | 66.7 (3) | C15—C14—C19—C18 | 1.6 (4) |
C5—C6—C7—N1 | −83.0 (3) | C2—C14—C19—C18 | −180.0 (3) |
C5—C6—C7—C20 | 155.8 (2) | N1—C7—C20—C21 | 91.8 (3) |
C5—N4—C8—O8 | 137.8 (3) | C6—C7—C20—C21 | −145.3 (3) |
C3—N4—C8—O8 | −30.4 (4) | N1—C7—C20—C25 | −86.8 (3) |
C5—N4—C8—C9 | −46.8 (3) | C6—C7—C20—C25 | 36.1 (3) |
C3—N4—C8—C9 | 145.0 (2) | C25—C20—C21—C22 | 0.1 (4) |
C11—O10—C9—C13 | 0.2 (3) | C7—C20—C21—C22 | −178.6 (3) |
C11—O10—C9—C8 | −175.1 (3) | C20—C21—C22—C23 | 0.0 (5) |
O8—C8—C9—C13 | −22.6 (4) | C21—C22—C23—C24 | 0.0 (5) |
N4—C8—C9—C13 | 162.0 (3) | C22—C23—C24—C25 | 0.0 (5) |
O8—C8—C9—O10 | 151.8 (3) | C23—C24—C25—C20 | 0.1 (5) |
N4—C8—C9—O10 | −23.6 (4) | C21—C20—C25—C24 | −0.1 (4) |
C9—O10—C11—C12 | −1.2 (4) | C7—C20—C25—C24 | 178.5 (3) |
O10—C11—C12—C13 | 1.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O5i | 0.95 | 2.50 | 3.322 (4) | 144 |
C19—H19···O8ii | 0.95 | 2.59 | 3.342 (4) | 136 |
C24—H24···O8iii | 0.95 | 2.39 | 3.278 (4) | 155 |
C11—H11···Cg3iv | 0.95 | 2.69 | 3.538 (4) | 149 |
C15—H15···Cg2v | 0.95 | 3.02 | 3.925 (4) | 160 |
C17—H17···Cg1i | 0.95 | 3.24 | 4.008 (4) | 140 |
C22—H22···Cg2vi | 0.95 | 2.72 | 3.540 (3) | 145 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1; (ii) x−1/2, −y+1/2, z; (iii) −x+3/2, y−1/2, z+1/2; (iv) −x+3/2, y+1/2, z+1/2; (v) x+1/2, −y+1/2, z; (vi) −x+2, −y, z+1/2. |
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