Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015306/na6093sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015306/na6093IIIsup2.hkl |
CCDC reference: 175364
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.175
- Data-to-parameter ratio = 17.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54052 General Notes
RADNW_01 The radiation wavelength given implies that Cu Kalpha1 has been used. Please check that this is correct. Wavelength given = 1.54052
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Compound (III) was prepared according to the method depicted on Scheme 1. A mixture 0.015 mol (4.00 g) of (I) and 0.030 mol (4.20 g) of p-phenetidine in 600 ml of anhydrous etanol in the presence of anhydrous sodium carbonate (0.075 mol, 8.00 g) was heated under reflux for 10 h (Mikiciuk-Olasik et al., 1993, 1994). The mixture was filtered and the solvent was distilled off. Compounds (II), (III) and a small amount of (IV) were isolated by fractional crystallization of the solid residue. Data for (III): yield 20%; m.p. 454.2 K. Elemental analyis (calculated/found): C 68.55/68.53%, H 6.98/7.09%, N 11.42/11.24%. IR (cm-1): 3200, 1590 (NH); 1670, 1520 (NH—CO). 1H NMR (in DMSO/TMS, chemical shifts in p.p.m.): 1.4 (t,6H, 2CH3CH2, J = 7 Hz), 2.35 (s, 6H, 2CH3Ph), 3.7 (d, 4H, 2CH2NH, J = 6 Hz), 4.05 (q, 4H, 2CH2CH3, J = 7 Hz), 5.65 (t,2H, 2NHCH2, J = 6 Hz) 6.9 (m, 10 Har), 9.6 (s, 2 H, NHCO).
Because collected data were relatively weak, there is a large amount of reflections with small intensities, and thus a part of reflections was marked as unobserved. This affect fraction of unique reflections observed (out to θ = 80.79°) which is equal to 96%.
All H atoms, except of these bonded to N atoms, were set in calculated positions. The H atoms bonded to N atoms were located in difference Fourier syntheses, calculated after four cycles of anistropic refinement. All H atoms were treated as riding on the adjacent C atom. The methyl groups were allowed to rotate about their local threefold axis.
Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997).
C28H34N4O4 | F(000) = 1048 |
Mr = 490.59 | Dx = 1.225 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54052 Å |
a = 14.6542 (11) Å | Cell parameters from 99 reflections |
b = 14.3344 (14) Å | θ = 5–60° |
c = 12.7220 (12) Å | µ = 0.67 mm−1 |
β = 95.606 (9)° | T = 293 K |
V = 2659.6 (4) Å3 | Sphere, colourless |
Z = 4 | 0.46 mm (radius) |
Kuma KM-4 diffractometer | 3352 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 80.8°, θmin = 3.0° |
ω–2θ scans | h = −18→18 |
Absorption correction: numerical X-RED. Stoe & Cie (1999) | k = −18→0 |
Tmin = 0.713, Tmax = 0.789 | l = −16→0 |
6127 measured reflections | 2 standard reflections every 100 reflections |
5857 independent reflections | intensity decay: −3.1% |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1016P)2] where P = (Fo2 + 2Fc2)/3 |
5857 reflections | (Δ/σ)max = 0.001 |
345 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C28H34N4O4 | V = 2659.6 (4) Å3 |
Mr = 490.59 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 14.6542 (11) Å | µ = 0.67 mm−1 |
b = 14.3344 (14) Å | T = 293 K |
c = 12.7220 (12) Å | 0.46 mm (radius) |
β = 95.606 (9)° |
Kuma KM-4 diffractometer | 3352 reflections with I > 2σ(I) |
Absorption correction: numerical X-RED. Stoe & Cie (1999) | Rint = 0.040 |
Tmin = 0.713, Tmax = 0.789 | 2 standard reflections every 100 reflections |
6127 measured reflections | intensity decay: −3.1% |
5857 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.175 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.35 e Å−3 |
5857 reflections | Δρmin = −0.42 e Å−3 |
345 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 | ||
N11 | 0.84417 (12) | 0.11954 (12) | 0.21384 (13) | 0.0456 (4) | |
H11 | 0.8428 (18) | 0.1569 (19) | 0.156 (2) | 0.072 (8)* | |
N12 | 1.02773 (13) | −0.03087 (13) | 0.14878 (16) | 0.0529 (5) | |
H12 | 1.0132 (18) | −0.063 (2) | 0.206 (2) | 0.073 (8)* | |
N22 | 1.04211 (14) | 0.11570 (14) | 0.50303 (15) | 0.0559 (5) | |
H22 | 1.0650 (18) | 0.071 (2) | 0.542 (2) | 0.074 (8)* | |
N21 | 0.86368 (13) | 0.13160 (13) | 0.43812 (13) | 0.0478 (4) | |
H21 | 0.9119 (17) | 0.0977 (18) | 0.4173 (19) | 0.064 (7)* | |
C11 | 0.90943 (14) | 0.05421 (13) | 0.22644 (14) | 0.0410 (4) | |
O11 | 0.91098 (10) | −0.00658 (10) | 0.29543 (11) | 0.0508 (4) | |
C12 | 0.98489 (15) | 0.06012 (14) | 0.15401 (16) | 0.0468 (5) | |
H12A | 0.9597 | 0.0793 | 0.0840 | 0.056* | |
H12B | 1.0301 | 0.1059 | 0.1807 | 0.056* | |
C13 | 1.12020 (15) | −0.03765 (14) | 0.13222 (16) | 0.0474 (5) | |
C14 | 1.16247 (16) | 0.02484 (17) | 0.06861 (18) | 0.0561 (5) | |
H14 | 1.1288 | 0.0738 | 0.0363 | 0.067* | |
C15 | 1.25334 (17) | 0.01484 (19) | 0.0531 (2) | 0.0630 (6) | |
H15 | 1.2803 | 0.0574 | 0.0104 | 0.076* | |
C16 | 1.30561 (15) | −0.05708 (17) | 0.09968 (19) | 0.0559 (5) | |
C17 | 1.26422 (17) | −0.11996 (16) | 0.1618 (2) | 0.0615 (6) | |
H17 | 1.2980 | −0.1692 | 0.1932 | 0.074* | |
C18 | 1.17292 (17) | −0.11017 (16) | 0.1775 (2) | 0.0596 (6) | |
H18 | 1.1460 | −0.1533 | 0.2196 | 0.072* | |
O22 | 1.27930 (12) | 0.24313 (14) | 0.21812 (15) | 0.0742 (5) | |
C19 | 1.45375 (18) | −0.1258 (2) | 0.1353 (3) | 0.0798 (8) | |
H19A | 1.4326 | −0.1887 | 0.1189 | 0.096* | |
H19B | 1.4527 | −0.1158 | 0.2105 | 0.096* | |
C20 | 1.54883 (18) | −0.1138 (2) | 0.1055 (3) | 0.0856 (9) | |
H20A | 1.5872 | −0.1623 | 0.1374 | 0.128* | |
H20B | 1.5722 | −0.0542 | 0.1299 | 0.128* | |
H20C | 1.5484 | −0.1170 | 0.0301 | 0.128* | |
C21 | 0.88984 (17) | 0.18740 (15) | 0.51997 (15) | 0.0508 (5) | |
O21 | 0.83888 (13) | 0.24215 (13) | 0.55980 (14) | 0.0735 (5) | |
C22 | 0.98910 (17) | 0.17713 (18) | 0.56309 (17) | 0.0592 (6) | |
H22A | 1.0175 | 0.2383 | 0.5657 | 0.071* | |
H22B | 0.9914 | 0.1539 | 0.6349 | 0.071* | |
C23 | 1.09861 (15) | 0.15168 (15) | 0.42914 (16) | 0.0499 (5) | |
C24 | 1.08878 (17) | 0.24018 (15) | 0.38781 (18) | 0.0554 (5) | |
H24 | 1.0425 | 0.2788 | 0.4079 | 0.066* | |
C25 | 1.14737 (16) | 0.27251 (17) | 0.3162 (2) | 0.0594 (6) | |
H25 | 1.1401 | 0.3326 | 0.2890 | 0.071* | |
C26 | 1.21589 (16) | 0.21646 (18) | 0.28515 (19) | 0.0581 (6) | |
C27 | 1.22402 (17) | 0.12631 (17) | 0.3228 (2) | 0.0616 (6) | |
H27 | 1.2688 | 0.0871 | 0.3003 | 0.074* | |
C28 | 1.16621 (17) | 0.09416 (16) | 0.3935 (2) | 0.0600 (6) | |
H28 | 1.1721 | 0.0331 | 0.4180 | 0.072* | |
O12 | 1.39578 (11) | −0.06082 (14) | 0.07858 (16) | 0.0763 (5) | |
C29 | 1.2681 (2) | 0.3325 (2) | 0.1692 (3) | 0.0807 (8) | |
H29A | 1.2708 | 0.3810 | 0.2225 | 0.097* | |
H29B | 1.2090 | 0.3361 | 0.1277 | 0.097* | |
C30 | 1.3430 (2) | 0.3454 (3) | 0.1000 (3) | 0.1025 (12) | |
H30A | 1.3368 | 0.4053 | 0.0662 | 0.154* | |
H30B | 1.3396 | 0.2973 | 0.0473 | 0.154* | |
H30C | 1.4012 | 0.3421 | 0.1417 | 0.154* | |
C1 | 0.76626 (13) | 0.12260 (13) | 0.27291 (16) | 0.0435 (4) | |
C6 | 0.77559 (14) | 0.12718 (13) | 0.38237 (15) | 0.0440 (4) | |
C5 | 0.69742 (17) | 0.12808 (16) | 0.4351 (2) | 0.0591 (6) | |
H5 | 0.7034 | 0.1291 | 0.5086 | 0.071* | |
C4 | 0.61043 (17) | 0.12750 (16) | 0.3814 (3) | 0.0666 (7) | |
C3 | 0.60123 (16) | 0.12781 (18) | 0.2717 (2) | 0.0680 (7) | |
C2 | 0.67977 (16) | 0.12368 (17) | 0.2198 (2) | 0.0601 (6) | |
H2 | 0.6740 | 0.1216 | 0.1464 | 0.072* | |
C7 | 0.5083 (2) | 0.1321 (3) | 0.2096 (4) | 0.1143 (14) | |
H7A | 0.4762 | 0.1866 | 0.2298 | 0.171* | |
H7B | 0.4738 | 0.0773 | 0.2238 | 0.171* | |
H7C | 0.5157 | 0.1350 | 0.1355 | 0.171* | |
C8 | 0.5283 (2) | 0.1255 (2) | 0.4459 (4) | 0.1080 (13) | |
H8A | 0.5493 | 0.1253 | 0.5198 | 0.162* | |
H8B | 0.4928 | 0.0702 | 0.4289 | 0.162* | |
H8C | 0.4909 | 0.1796 | 0.4297 | 0.162* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0532 (9) | 0.0457 (9) | 0.0388 (8) | 0.0084 (8) | 0.0084 (7) | 0.0050 (7) |
N12 | 0.0510 (10) | 0.0451 (10) | 0.0655 (12) | 0.0029 (8) | 0.0200 (9) | −0.0016 (9) |
N22 | 0.0651 (12) | 0.0507 (10) | 0.0510 (10) | 0.0043 (9) | 0.0013 (9) | 0.0081 (9) |
N21 | 0.0565 (10) | 0.0498 (10) | 0.0375 (8) | 0.0048 (8) | 0.0071 (7) | −0.0063 (7) |
C11 | 0.0488 (10) | 0.0365 (9) | 0.0379 (9) | 0.0017 (8) | 0.0053 (8) | −0.0026 (7) |
O11 | 0.0651 (9) | 0.0435 (7) | 0.0456 (7) | 0.0102 (7) | 0.0145 (7) | 0.0068 (6) |
C12 | 0.0556 (12) | 0.0425 (10) | 0.0434 (10) | 0.0033 (9) | 0.0107 (9) | 0.0017 (8) |
C13 | 0.0543 (11) | 0.0417 (10) | 0.0474 (11) | 0.0004 (9) | 0.0102 (9) | −0.0047 (8) |
C14 | 0.0533 (12) | 0.0603 (13) | 0.0555 (13) | 0.0068 (10) | 0.0088 (10) | 0.0122 (10) |
C15 | 0.0582 (14) | 0.0683 (15) | 0.0642 (14) | 0.0016 (12) | 0.0155 (11) | 0.0157 (12) |
C16 | 0.0485 (12) | 0.0547 (12) | 0.0655 (13) | 0.0031 (10) | 0.0111 (10) | 0.0022 (10) |
C17 | 0.0598 (14) | 0.0466 (12) | 0.0798 (16) | 0.0081 (10) | 0.0151 (12) | 0.0087 (11) |
C18 | 0.0622 (14) | 0.0478 (12) | 0.0721 (15) | 0.0025 (10) | 0.0236 (12) | 0.0079 (11) |
O22 | 0.0676 (11) | 0.0784 (12) | 0.0792 (12) | 0.0094 (9) | 0.0200 (10) | 0.0166 (10) |
C19 | 0.0602 (15) | 0.0691 (17) | 0.112 (2) | 0.0124 (13) | 0.0162 (15) | 0.0152 (16) |
C20 | 0.0543 (14) | 0.087 (2) | 0.116 (2) | 0.0091 (14) | 0.0095 (15) | 0.0121 (18) |
C21 | 0.0719 (14) | 0.0493 (11) | 0.0320 (9) | −0.0004 (10) | 0.0092 (9) | 0.0001 (8) |
O21 | 0.0829 (12) | 0.0740 (12) | 0.0649 (10) | 0.0080 (9) | 0.0134 (9) | −0.0281 (9) |
C22 | 0.0723 (15) | 0.0632 (14) | 0.0407 (10) | −0.0007 (12) | −0.0018 (10) | −0.0030 (10) |
C23 | 0.0569 (12) | 0.0453 (11) | 0.0451 (10) | 0.0019 (9) | −0.0064 (9) | 0.0008 (8) |
C24 | 0.0590 (12) | 0.0479 (12) | 0.0584 (13) | 0.0074 (10) | 0.0019 (10) | 0.0048 (10) |
C25 | 0.0615 (13) | 0.0512 (12) | 0.0649 (14) | 0.0067 (11) | 0.0030 (11) | 0.0101 (11) |
C26 | 0.0552 (13) | 0.0609 (13) | 0.0572 (13) | 0.0018 (11) | 0.0010 (10) | 0.0028 (11) |
C27 | 0.0592 (13) | 0.0570 (14) | 0.0684 (15) | 0.0129 (11) | 0.0066 (11) | 0.0015 (11) |
C28 | 0.0662 (14) | 0.0447 (11) | 0.0679 (14) | 0.0087 (10) | 0.0000 (12) | 0.0035 (10) |
O12 | 0.0483 (9) | 0.0812 (12) | 0.1014 (14) | 0.0065 (8) | 0.0171 (9) | 0.0273 (11) |
C29 | 0.0644 (16) | 0.093 (2) | 0.0837 (19) | 0.0072 (15) | 0.0042 (14) | 0.0300 (16) |
C30 | 0.078 (2) | 0.132 (3) | 0.102 (2) | 0.005 (2) | 0.0269 (18) | 0.044 (2) |
C1 | 0.0459 (10) | 0.0372 (9) | 0.0481 (10) | 0.0049 (8) | 0.0084 (8) | −0.0021 (8) |
C6 | 0.0475 (10) | 0.0402 (10) | 0.0455 (10) | 0.0030 (8) | 0.0109 (8) | 0.0000 (8) |
C5 | 0.0672 (15) | 0.0525 (12) | 0.0615 (13) | 0.0017 (11) | 0.0254 (12) | 0.0025 (10) |
C4 | 0.0555 (13) | 0.0457 (12) | 0.103 (2) | 0.0029 (10) | 0.0302 (14) | −0.0008 (13) |
C3 | 0.0475 (12) | 0.0561 (14) | 0.099 (2) | 0.0056 (10) | 0.0013 (13) | −0.0187 (13) |
C2 | 0.0542 (13) | 0.0564 (13) | 0.0675 (14) | 0.0109 (10) | −0.0045 (11) | −0.0123 (11) |
C7 | 0.0560 (16) | 0.122 (3) | 0.159 (4) | 0.0217 (18) | −0.020 (2) | −0.045 (3) |
C8 | 0.0648 (18) | 0.089 (2) | 0.181 (4) | 0.0046 (16) | 0.070 (2) | 0.010 (2) |
N11—C11 | 1.337 (2) | C21—O21 | 1.226 (3) |
N11—C1 | 1.427 (2) | C21—C22 | 1.511 (3) |
N11—H11 | 0.91 (3) | C22—H22A | 0.9700 |
N12—C13 | 1.395 (3) | C22—H22B | 0.9700 |
N12—C12 | 1.452 (3) | C23—C24 | 1.375 (3) |
N12—H12 | 0.91 (3) | C23—C28 | 1.398 (3) |
N22—C23 | 1.410 (3) | C24—C25 | 1.391 (3) |
N22—C22 | 1.442 (3) | C24—H24 | 0.9300 |
N22—H22 | 0.85 (3) | C25—C26 | 1.374 (3) |
N21—C21 | 1.339 (3) | C25—H25 | 0.9300 |
N21—C6 | 1.412 (3) | C26—C27 | 1.380 (3) |
N21—H21 | 0.92 (3) | C27—C28 | 1.374 (3) |
C11—O11 | 1.235 (2) | C27—H27 | 0.9300 |
C11—C12 | 1.509 (3) | C28—H28 | 0.9300 |
C12—H12A | 0.9700 | C29—C30 | 1.485 (4) |
C12—H12B | 0.9700 | C29—H29A | 0.9700 |
C13—C18 | 1.387 (3) | C29—H29B | 0.9700 |
C13—C14 | 1.392 (3) | C30—H30A | 0.9600 |
C14—C15 | 1.372 (3) | C30—H30B | 0.9600 |
C14—H14 | 0.9300 | C30—H30C | 0.9600 |
C15—C16 | 1.383 (3) | C1—C2 | 1.377 (3) |
C15—H15 | 0.9300 | C1—C6 | 1.387 (3) |
C16—O12 | 1.375 (3) | C6—C5 | 1.383 (3) |
C16—C17 | 1.378 (3) | C5—C4 | 1.386 (4) |
C17—C18 | 1.379 (3) | C5—H5 | 0.9300 |
C17—H17 | 0.9300 | C4—C3 | 1.389 (4) |
C18—H18 | 0.9300 | C4—C8 | 1.522 (3) |
O22—C26 | 1.375 (3) | C3—C2 | 1.383 (3) |
O22—C29 | 1.427 (3) | C3—C7 | 1.508 (4) |
C19—O12 | 1.410 (3) | C2—H2 | 0.9300 |
C19—C20 | 1.489 (4) | C7—H7A | 0.9600 |
C19—H19A | 0.9700 | C7—H7B | 0.9600 |
C19—H19B | 0.9700 | C7—H7C | 0.9600 |
C20—H20A | 0.9600 | C8—H8A | 0.9600 |
C20—H20B | 0.9600 | C8—H8B | 0.9600 |
C20—H20C | 0.9600 | C8—H8C | 0.9600 |
C11—N11—C1 | 123.91 (17) | C24—C23—C28 | 118.1 (2) |
C11—N11—H11 | 117.9 (17) | C24—C23—N22 | 123.1 (2) |
C1—N11—H11 | 117.0 (17) | C28—C23—N22 | 118.8 (2) |
C13—N12—C12 | 120.02 (18) | C23—C24—C25 | 120.6 (2) |
C13—N12—H12 | 113.1 (17) | C23—C24—H24 | 119.7 |
C12—N12—H12 | 106.8 (17) | C25—C24—H24 | 119.7 |
C23—N22—C22 | 120.8 (2) | C26—C25—C24 | 120.6 (2) |
C23—N22—H22 | 115.6 (18) | C26—C25—H25 | 119.7 |
C22—N22—H22 | 110.7 (19) | C24—C25—H25 | 119.7 |
C21—N21—C6 | 126.54 (19) | C25—C26—O22 | 124.9 (2) |
C21—N21—H21 | 111.8 (16) | C25—C26—C27 | 119.3 (2) |
C6—N21—H21 | 121.5 (16) | O22—C26—C27 | 115.8 (2) |
O11—C11—N11 | 122.85 (18) | C28—C27—C26 | 120.3 (2) |
O11—C11—C12 | 120.64 (17) | C28—C27—H27 | 119.9 |
N11—C11—C12 | 116.46 (17) | C26—C27—H27 | 119.9 |
N12—C12—C11 | 108.87 (17) | C27—C28—C23 | 121.1 (2) |
N12—C12—H12A | 109.9 | C27—C28—H28 | 119.5 |
C11—C12—H12A | 109.9 | C23—C28—H28 | 119.5 |
N12—C12—H12B | 109.9 | C16—O12—C19 | 117.9 (2) |
C11—C12—H12B | 109.9 | O22—C29—C30 | 108.1 (3) |
H12A—C12—H12B | 108.3 | O22—C29—H29A | 110.1 |
C18—C13—C14 | 117.5 (2) | C30—C29—H29A | 110.1 |
C18—C13—N12 | 120.0 (2) | O22—C29—H29B | 110.1 |
C14—C13—N12 | 122.5 (2) | C30—C29—H29B | 110.1 |
C15—C14—C13 | 120.6 (2) | H29A—C29—H29B | 108.4 |
C15—C14—H14 | 119.7 | C29—C30—H30A | 109.5 |
C13—C14—H14 | 119.7 | C29—C30—H30B | 109.5 |
C14—C15—C16 | 121.4 (2) | H30A—C30—H30B | 109.5 |
C14—C15—H15 | 119.3 | C29—C30—H30C | 109.5 |
C16—C15—H15 | 119.3 | H30A—C30—H30C | 109.5 |
O12—C16—C17 | 124.9 (2) | H30B—C30—H30C | 109.5 |
O12—C16—C15 | 116.6 (2) | C2—C1—C6 | 119.20 (19) |
C17—C16—C15 | 118.5 (2) | C2—C1—N11 | 119.15 (19) |
C16—C17—C18 | 120.3 (2) | C6—C1—N11 | 121.62 (18) |
C16—C17—H17 | 119.9 | C5—C6—C1 | 118.8 (2) |
C18—C17—H17 | 119.9 | C5—C6—N21 | 121.04 (19) |
C17—C18—C13 | 121.7 (2) | C1—C6—N21 | 120.11 (17) |
C17—C18—H18 | 119.2 | C6—C5—C4 | 121.7 (2) |
C13—C18—H18 | 119.2 | C6—C5—H5 | 119.1 |
C26—O22—C29 | 117.6 (2) | C4—C5—H5 | 119.1 |
O12—C19—C20 | 109.0 (2) | C5—C4—C3 | 119.3 (2) |
O12—C19—H19A | 109.9 | C5—C4—C8 | 118.2 (3) |
C20—C19—H19A | 109.9 | C3—C4—C8 | 122.5 (3) |
O12—C19—H19B | 109.9 | C2—C3—C4 | 118.4 (2) |
C20—C19—H19B | 109.9 | C2—C3—C7 | 120.2 (3) |
H19A—C19—H19B | 108.3 | C4—C3—C7 | 121.4 (3) |
C19—C20—H20A | 109.5 | C1—C2—C3 | 122.3 (2) |
C19—C20—H20B | 109.5 | C1—C2—H2 | 118.8 |
H20A—C20—H20B | 109.5 | C3—C2—H2 | 118.8 |
C19—C20—H20C | 109.5 | C3—C7—H7A | 109.5 |
H20A—C20—H20C | 109.5 | C3—C7—H7B | 109.5 |
H20B—C20—H20C | 109.5 | H7A—C7—H7B | 109.5 |
O21—C21—N21 | 124.3 (2) | C3—C7—H7C | 109.5 |
O21—C21—C22 | 121.1 (2) | H7A—C7—H7C | 109.5 |
N21—C21—C22 | 114.61 (19) | H7B—C7—H7C | 109.5 |
N22—C22—C21 | 114.62 (18) | C4—C8—H8A | 109.5 |
N22—C22—H22A | 108.6 | C4—C8—H8B | 109.5 |
C21—C22—H22A | 108.6 | H8A—C8—H8B | 109.5 |
N22—C22—H22B | 108.6 | C4—C8—H8C | 109.5 |
C21—C22—H22B | 108.6 | H8A—C8—H8C | 109.5 |
H22A—C22—H22B | 107.6 | H8B—C8—H8C | 109.5 |
C6—C1—N11—C11 | 57.6 (3) | N21—C21—C22—N22 | 5.8 (3) |
C1—N11—C11—C12 | 177.75 (18) | C21—C22—N22—C23 | 98.6 (3) |
N11—C11—C12—N12 | −158.31 (18) | C22—N22—C23—C24 | −18.6 (3) |
C11—C12—N12—C13 | −149.63 (19) | C15—C16—O12—C19 | 172.0 (3) |
C12—N12—C13—C14 | −34.7 (3) | C16—O12—C19—C20 | −176.3 (3) |
C1—C6—N21—C21 | 136.3 (2) | C25—C26—O22—C29 | −6.2 (4) |
C6—N21—C21—C22 | −179.5 (2) | C26—O22—C29—C30 | −179.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O21i | 0.91 (3) | 1.89 (3) | 2.783 (2) | 166 (2) |
N12—H12···O11 | 0.91 (3) | 2.13 (3) | 2.675 (2) | 118 (2) |
N22—H22···O11ii | 0.85 (3) | 2.27 (3) | 3.025 (2) | 148 (3) |
N21—H21···N22 | 0.92 (3) | 2.12 (3) | 2.674 (3) | 118 (2) |
N21—H21···O11 | 0.92 (3) | 2.15 (3) | 2.819 (2) | 129 (2) |
C5—H5···O21 | 0.93 | 2.60 | 2.974 (3) | 105 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H34N4O4 |
Mr | 490.59 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.6542 (11), 14.3344 (14), 12.7220 (12) |
β (°) | 95.606 (9) |
V (Å3) | 2659.6 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.67 |
Crystal size (mm) | 0.46 (radius) |
Data collection | |
Diffractometer | Kuma KM-4 diffractometer |
Absorption correction | Numerical X-RED. Stoe & Cie (1999) |
Tmin, Tmax | 0.713, 0.789 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6127, 5857, 3352 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.175, 1.05 |
No. of reflections | 5857 |
No. of parameters | 345 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.42 |
Computer programs: KM-4 Software (Kuma, 1993), KM-4 Software, DATAPROC (Gałdecki et al., 1998), SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997).
C6—C1—N11—C11 | 57.6 (3) | N21—C21—C22—N22 | 5.8 (3) |
C1—N11—C11—C12 | 177.75 (18) | C21—C22—N22—C23 | 98.6 (3) |
N11—C11—C12—N12 | −158.31 (18) | C22—N22—C23—C24 | −18.6 (3) |
C11—C12—N12—C13 | −149.63 (19) | C15—C16—O12—C19 | 172.0 (3) |
C12—N12—C13—C14 | −34.7 (3) | C16—O12—C19—C20 | −176.3 (3) |
C1—C6—N21—C21 | 136.3 (2) | C25—C26—O22—C29 | −6.2 (4) |
C6—N21—C21—C22 | −179.5 (2) | C26—O22—C29—C30 | −179.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O21i | 0.91 (3) | 1.89 (3) | 2.783 (2) | 166 (2) |
N12—H12···O11 | 0.91 (3) | 2.13 (3) | 2.675 (2) | 118 (2) |
N22—H22···O11ii | 0.85 (3) | 2.27 (3) | 3.025 (2) | 148 (3) |
N21—H21···N22 | 0.92 (3) | 2.12 (3) | 2.674 (3) | 118 (2) |
N21—H21···O11 | 0.92 (3) | 2.15 (3) | 2.819 (2) | 129 (2) |
C5—H5···O21 | 0.93 | 2.60 | 2.974 (3) | 105 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z+1. |
The present work is a continuation of our previous studies on derivatives of 2,3,4,5,6,7-hexahydro-1H-1,4,7-benzotriazone-2,5-dione. Upon introduction of pharmacophoric substituents for a desired activity into those systems, it is expected that derivatives will be obtained exhibiting numerous favourable properties, such as analeptic activity or possible anticancer and anti-HIV activities (Bartczak et al., 1995). Within this area of research, the preliminary results of determining the crystal structure of the title compound were previously published (Mikiciuk-Olasik et al., 1993), but the complete structure was never determined. Thus, we now present a full structure of the N,N'-bis[(4-ethoxyphenyl)aminoacetyl]-4,5-dimethyl-o-phenylenediamine [Cambridge Structural Database (CSD; Allen and Kennard, 1993) refcode: WEWPIX (the preliminary studies)].
The perspective view of the title compound, (III), together with the atom-numbering scheme is shown in Fig. 1. A l l interatomic distances can be considered normal. Atoms C7, C8 and C30 show signs of disorder (particularly high values of Ueq), but all attempts to find model of disorder fail. Thus, it can be supposed dynamical character of disorder. The all atoms of the (4-ethoxyphenyl)amino parts of the respective side branches are almost coplanar. The maximum deviation in the N11 branch is 0.058 (2) Å for O12 (branch A hereafter) and the maximum deviation in the N21 branch is 0.046 (2) Å for O22 (branch B hereafter). The next bonded C atom Cx2 deviates by 0.740 (2) and 0.425 (2) Å from the above planes, respectively (where x = 1 for the atoms of the branch A and x = 2 for the atoms of the branch B). These planes make a dihedral angle of 27.37 (5)°. The main difference between branches A and B is the conformation of the chain consisting of Nx1, Cx1, Cx2 and Nx2 (best described by the torsion angles, see Table 1 for details). The overall arrangement of the side branches seems to be imposed partly by the N12—H12···O11 hydrogen bond and the C5—H5···O21 weak hydrogen bond (Desiraju & Steiner, 1999) (branch A), and by the N21—H21···N22 hydrogen bond (branch B); for details, see Table 2. The substituents are stabilized by interbranch N21—H21···O11 hydrogen bond (Jeffrey & Saenger, 1994). The N21 atom acts as a donor for two intramolecular hydrogen bonds and these hydrogen bonds are created via the same hydrogen atom (H21). The structure of the title compound is assembled by intermolecular N—H···O hydrogen bonds, to form a two-dimensional framework (Fig. 2 and Table 2). There are no unusual intermolecular short contacts, except for the hydrogen bonds described in Table 2.