organic compounds
Dibutyl 5-[(4-ethoxycarbonylphenyl)diazenyl]benzene-1,3-dicarboxylate
aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, 252059, People's Republic of China
*Correspondence e-mail: yllctu@yahoo.com.cn
In the title compound, C25H30N2O6, the dihedral angle between the aromatic rings is 3.79 (1) Å and the N=N bond shows a trans conformation. Both butyl side chains show evidence of disorder.
Related literature
For general background to dendrimers related to the title compound, see: Tomalia et al. (1990); Bosman et al. (1999). For a related structure, see: Wang et al. (2004).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536810022762/hb5477sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810022762/hb5477Isup2.hkl
A yellow powder of ethyl 4-((dibutyl-3',5'-biscarbonylphenyl)diazenyl)benzoate (Jinan Henghua Science & Technology Co. Ltd.) (1 mmol 0.45 g) was dissolved in 10 ml ethanol and evaporated in an open flask at room temperature. Three days later, orange blocks of (I) were obained. Anal. C25H30N2O6: C, 66.01; H, 6.60; N, 6.16%. Found: C, 65.98; H, 6.47; N, 6.05%.
Hydrogen atoms were placed in geometrically calculated positions (C—H 0.95 Å for aromatic and formyl, 0.99 Å for methylene and 0.98 Å for methyl) and included in the
in a riding motion approximation with Uiso(H) = 1.2Ueq(C) [for methyl groups Uiso(H) = 1.5Ueq(C)].Data collection: APEX2 (Bruker, 2004); cell
SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular sturcture of (I) with displacement ellipsoids drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius. |
C25H30N2O6 | Z = 2 |
Mr = 454.51 | F(000) = 484 |
Triclinic, P1 | Dx = 1.221 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.675 (2) Å | Cell parameters from 2660 reflections |
b = 11.299 (3) Å | θ = 2.5–27.1° |
c = 13.636 (3) Å | µ = 0.09 mm−1 |
α = 97.311 (3)° | T = 293 K |
β = 94.806 (3)° | Block, yellow |
γ = 109.793 (2)° | 0.12 × 0.10 × 0.08 mm |
V = 1235.8 (5) Å3 |
Bruker APEXII CCD diffractometer | 4275 independent reflections |
Radiation source: fine-focus sealed tube | 2736 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −10→10 |
Tmin = 0.990, Tmax = 0.993 | k = −13→13 |
8643 measured reflections | l = −15→16 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.218 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1149P)2 + 0.3064P] where P = (Fo2 + 2Fc2)/3 |
4275 reflections | (Δ/σ)max < 0.001 |
302 parameters | Δρmax = 0.55 e Å−3 |
13 restraints | Δρmin = −0.32 e Å−3 |
C25H30N2O6 | γ = 109.793 (2)° |
Mr = 454.51 | V = 1235.8 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.675 (2) Å | Mo Kα radiation |
b = 11.299 (3) Å | µ = 0.09 mm−1 |
c = 13.636 (3) Å | T = 293 K |
α = 97.311 (3)° | 0.12 × 0.10 × 0.08 mm |
β = 94.806 (3)° |
Bruker APEXII CCD diffractometer | 4275 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2736 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.993 | Rint = 0.022 |
8643 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 13 restraints |
wR(F2) = 0.218 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.55 e Å−3 |
4275 reflections | Δρmin = −0.32 e Å−3 |
302 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 | 1.0434 (3) | 0.2950 (2) | 0.48258 (15) | 0.0725 (6) | |
O2 | 0.8502 (3) | 0.3718 (2) | 0.52977 (16) | 0.0932 (8) | |
O3 | 0.7562 (3) | −0.0204 (2) | 0.05822 (16) | 0.0871 (7) | |
O4 | 0.9356 (3) | −0.0106 (2) | 0.18814 (15) | 0.0810 (7) | |
O5 | −0.2310 (2) | 0.3824 (2) | 0.02977 (15) | 0.0714 (6) | |
O6 | −0.1835 (3) | 0.5354 (2) | 0.1600 (2) | 0.0974 (8) | |
N1 | 0.4477 (3) | 0.2563 (2) | 0.19969 (16) | 0.0588 (6) | |
N2 | 0.4018 (3) | 0.3269 (2) | 0.25818 (16) | 0.0577 (6) | |
C1 | 1.3390 (8) | −0.0964 (7) | 0.3283 (5) | 0.173 (3) | |
H1A | 1.3681 | −0.1621 | 0.2913 | 0.260* | |
H1B | 1.3211 | −0.1154 | 0.3940 | 0.260* | |
H1C | 1.4271 | −0.0159 | 0.3333 | 0.260* | |
C2 | 1.1938 (10) | −0.0905 (10) | 0.2790 (6) | 0.225 (4) | |
H2A | 1.1052 | −0.1568 | 0.3004 | 0.270* | |
H2B | 1.1878 | −0.0105 | 0.3104 | 0.270* | |
C3 | 1.1450 (9) | −0.0977 (7) | 0.1825 (5) | 0.189 (3) | |
H3A | 1.1593 | −0.1744 | 0.1507 | 0.227* | |
H3B | 1.2301 | −0.0275 | 0.1625 | 0.227* | |
C4 | 0.9940 (5) | −0.0991 (4) | 0.1300 (3) | 0.0905 (11) | |
H4A | 0.9116 | −0.1843 | 0.1198 | 0.109* | |
H4B | 1.0129 | −0.0745 | 0.0652 | 0.109* | |
C5 | 1.2579 (9) | 0.1314 (8) | 0.5848 (7) | 0.207 (4) | |
H5A | 1.2809 | 0.1655 | 0.6548 | 0.311* | |
H5B | 1.3017 | 0.0643 | 0.5720 | 0.311* | |
H5C | 1.1405 | 0.0980 | 0.5646 | 0.311* | |
C6 | 1.3321 (7) | 0.2288 (7) | 0.5303 (5) | 0.149 (2) | |
H6A | 1.2823 | 0.2014 | 0.4611 | 0.179* | |
H6B | 1.4485 | 0.2407 | 0.5327 | 0.179* | |
C7 | 1.3166 (5) | 0.3532 (4) | 0.5670 (4) | 0.1102 (14) | |
H7A | 1.3649 | 0.4117 | 0.5223 | 0.132* | |
H7B | 1.3831 | 0.3866 | 0.6319 | 0.132* | |
C8 | 1.1471 (4) | 0.3556 (3) | 0.5769 (2) | 0.0842 (10) | |
H8A | 1.1025 | 0.3102 | 0.6298 | 0.101* | |
H8B | 1.1516 | 0.4429 | 0.5931 | 0.101* | |
C9 | 0.8992 (4) | 0.3119 (3) | 0.4689 (2) | 0.0642 (8) | |
C10 | 0.8072 (3) | 0.2505 (2) | 0.36752 (19) | 0.0545 (7) | |
C11 | 0.8557 (3) | 0.1654 (2) | 0.3055 (2) | 0.0552 (7) | |
H11 | 0.9463 | 0.1446 | 0.3274 | 0.066* | |
C12 | 0.7685 (3) | 0.1118 (2) | 0.21106 (19) | 0.0527 (6) | |
C13 | 0.8165 (3) | 0.0201 (3) | 0.1433 (2) | 0.0615 (7) | |
C14 | 0.6346 (3) | 0.1444 (2) | 0.1786 (2) | 0.0569 (7) | |
H14 | 0.5769 | 0.1095 | 0.1150 | 0.068* | |
C15 | 0.5867 (3) | 0.2286 (2) | 0.24046 (19) | 0.0523 (6) | |
C16 | 0.6712 (3) | 0.2805 (2) | 0.33568 (19) | 0.0532 (6) | |
H16 | 0.6367 | 0.3351 | 0.3779 | 0.064* | |
C17 | 0.2637 (3) | 0.3539 (2) | 0.21661 (19) | 0.0523 (6) | |
C18 | 0.1725 (3) | 0.2944 (3) | 0.1236 (2) | 0.0603 (7) | |
H18 | 0.2007 | 0.2334 | 0.0842 | 0.072* | |
C19 | 0.0408 (3) | 0.3268 (3) | 0.0906 (2) | 0.0608 (7) | |
H19 | −0.0207 | 0.2868 | 0.0287 | 0.073* | |
C20 | −0.0022 (3) | 0.4184 (2) | 0.1480 (2) | 0.0538 (6) | |
C21 | 0.0888 (3) | 0.4765 (3) | 0.2404 (2) | 0.0631 (7) | |
H21 | 0.0611 | 0.5380 | 0.2796 | 0.076* | |
C22 | 0.2203 (3) | 0.4437 (3) | 0.2744 (2) | 0.0623 (7) | |
H22 | 0.2802 | 0.4824 | 0.3369 | 0.075* | |
C23 | −0.1457 (4) | 0.4536 (3) | 0.1153 (2) | 0.0629 (7) | |
C24 | −0.3775 (4) | 0.4066 (4) | −0.0072 (3) | 0.0835 (10) | |
H24A | −0.3473 | 0.4937 | −0.0197 | 0.100* | |
H24B | −0.4538 | 0.3948 | 0.0419 | 0.100* | |
C25 | −0.4555 (5) | 0.3171 (5) | −0.0998 (4) | 0.1176 (15) | |
H25A | −0.3772 | 0.3263 | −0.1467 | 0.176* | |
H25B | −0.5491 | 0.3349 | −0.1276 | 0.176* | |
H25C | −0.4913 | 0.2314 | −0.0860 | 0.176* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0697 (13) | 0.0861 (14) | 0.0657 (12) | 0.0446 (11) | −0.0120 (10) | −0.0074 (10) |
O2 | 0.0977 (17) | 0.1285 (19) | 0.0641 (13) | 0.0739 (16) | −0.0125 (12) | −0.0253 (13) |
O3 | 0.0918 (16) | 0.1085 (17) | 0.0657 (14) | 0.0566 (14) | −0.0027 (12) | −0.0195 (12) |
O4 | 0.0927 (16) | 0.0967 (15) | 0.0693 (13) | 0.0649 (13) | −0.0007 (11) | −0.0106 (11) |
O5 | 0.0609 (12) | 0.0868 (14) | 0.0751 (14) | 0.0419 (11) | −0.0039 (10) | 0.0088 (11) |
O6 | 0.0949 (17) | 0.1010 (17) | 0.1112 (19) | 0.0690 (15) | −0.0067 (14) | −0.0114 (14) |
N1 | 0.0510 (13) | 0.0669 (14) | 0.0607 (14) | 0.0285 (11) | 0.0006 (10) | 0.0014 (11) |
N2 | 0.0523 (13) | 0.0640 (13) | 0.0594 (13) | 0.0284 (11) | 0.0014 (10) | 0.0017 (10) |
C1 | 0.140 (5) | 0.215 (7) | 0.181 (6) | 0.091 (5) | −0.021 (4) | 0.043 (5) |
C2 | 0.186 (7) | 0.343 (12) | 0.185 (7) | 0.177 (8) | −0.038 (6) | −0.012 (7) |
C3 | 0.216 (6) | 0.243 (6) | 0.161 (5) | 0.188 (5) | −0.031 (4) | −0.049 (4) |
C4 | 0.099 (3) | 0.097 (2) | 0.091 (2) | 0.065 (2) | 0.0094 (19) | −0.0101 (18) |
C5 | 0.173 (6) | 0.213 (7) | 0.302 (10) | 0.105 (6) | 0.090 (7) | 0.137 (8) |
C6 | 0.108 (4) | 0.195 (6) | 0.185 (6) | 0.092 (4) | 0.028 (4) | 0.065 (5) |
C7 | 0.080 (3) | 0.120 (3) | 0.124 (3) | 0.036 (2) | −0.021 (2) | 0.019 (3) |
C8 | 0.084 (2) | 0.092 (2) | 0.073 (2) | 0.0434 (19) | −0.0254 (17) | −0.0106 (17) |
C9 | 0.0676 (18) | 0.0685 (17) | 0.0615 (17) | 0.0375 (15) | −0.0027 (14) | −0.0014 (13) |
C10 | 0.0532 (15) | 0.0577 (15) | 0.0550 (15) | 0.0260 (12) | 0.0036 (12) | 0.0025 (12) |
C11 | 0.0516 (15) | 0.0594 (15) | 0.0595 (16) | 0.0272 (12) | 0.0054 (12) | 0.0073 (12) |
C12 | 0.0508 (15) | 0.0538 (14) | 0.0560 (15) | 0.0226 (12) | 0.0106 (12) | 0.0036 (11) |
C13 | 0.0589 (17) | 0.0664 (17) | 0.0595 (18) | 0.0265 (14) | 0.0085 (14) | −0.0010 (13) |
C14 | 0.0537 (15) | 0.0601 (15) | 0.0551 (15) | 0.0213 (13) | 0.0033 (12) | 0.0027 (12) |
C15 | 0.0460 (14) | 0.0568 (14) | 0.0560 (15) | 0.0224 (12) | 0.0043 (12) | 0.0067 (11) |
C16 | 0.0524 (15) | 0.0555 (14) | 0.0548 (15) | 0.0259 (12) | 0.0070 (12) | 0.0011 (11) |
C17 | 0.0455 (14) | 0.0607 (15) | 0.0524 (14) | 0.0227 (12) | 0.0033 (11) | 0.0066 (11) |
C18 | 0.0578 (16) | 0.0670 (16) | 0.0602 (16) | 0.0338 (14) | 0.0028 (13) | −0.0046 (13) |
C19 | 0.0548 (16) | 0.0701 (17) | 0.0575 (16) | 0.0295 (13) | −0.0034 (12) | −0.0038 (13) |
C20 | 0.0486 (14) | 0.0554 (14) | 0.0606 (16) | 0.0229 (12) | 0.0065 (12) | 0.0089 (12) |
C21 | 0.0654 (18) | 0.0652 (16) | 0.0642 (17) | 0.0353 (14) | 0.0068 (14) | −0.0034 (13) |
C22 | 0.0608 (17) | 0.0711 (17) | 0.0546 (16) | 0.0312 (14) | −0.0024 (13) | −0.0064 (13) |
C23 | 0.0593 (17) | 0.0638 (16) | 0.0738 (19) | 0.0322 (14) | 0.0088 (15) | 0.0110 (14) |
C24 | 0.0625 (19) | 0.109 (3) | 0.094 (2) | 0.0478 (19) | −0.0003 (17) | 0.027 (2) |
C25 | 0.081 (3) | 0.141 (4) | 0.125 (3) | 0.045 (3) | −0.026 (2) | 0.012 (3) |
O1—C9 | 1.329 (3) | C7—H7A | 0.9700 |
O1—C8 | 1.448 (3) | C7—H7B | 0.9700 |
O2—C9 | 1.200 (3) | C8—H8A | 0.9700 |
O3—C13 | 1.196 (3) | C8—H8B | 0.9700 |
O4—C13 | 1.324 (3) | C9—C10 | 1.492 (4) |
O4—C4 | 1.447 (3) | C10—C16 | 1.385 (3) |
O5—C23 | 1.330 (3) | C10—C11 | 1.394 (3) |
O5—C24 | 1.452 (3) | C11—C12 | 1.388 (4) |
O6—C23 | 1.195 (3) | C11—H11 | 0.9300 |
N1—N2 | 1.240 (3) | C12—C14 | 1.388 (4) |
N1—C15 | 1.431 (3) | C12—C13 | 1.488 (3) |
N2—C17 | 1.423 (3) | C14—C15 | 1.383 (3) |
C1—C2 | 1.403 (7) | C14—H14 | 0.9300 |
C1—H1A | 0.9600 | C15—C16 | 1.386 (4) |
C1—H1B | 0.9600 | C16—H16 | 0.9300 |
C1—H1C | 0.9600 | C17—C22 | 1.378 (3) |
C2—C3 | 1.331 (7) | C17—C18 | 1.393 (4) |
C2—H2A | 0.9700 | C18—C19 | 1.372 (4) |
C2—H2B | 0.9700 | C18—H18 | 0.9300 |
C3—C4 | 1.434 (7) | C19—C20 | 1.388 (3) |
C3—H3A | 0.9700 | C19—H19 | 0.9300 |
C3—H3B | 0.9700 | C20—C21 | 1.384 (4) |
C4—H4A | 0.9700 | C20—C23 | 1.481 (4) |
C4—H4B | 0.9700 | C21—C22 | 1.377 (4) |
C5—C6 | 1.409 (8) | C21—H21 | 0.9300 |
C5—H5A | 0.9600 | C22—H22 | 0.9300 |
C5—H5B | 0.9600 | C24—C25 | 1.465 (5) |
C5—H5C | 0.9600 | C24—H24A | 0.9700 |
C6—C7 | 1.485 (7) | C24—H24B | 0.9700 |
C6—H6A | 0.9700 | C25—H25A | 0.9600 |
C6—H6B | 0.9700 | C25—H25B | 0.9600 |
C7—C8 | 1.496 (5) | C25—H25C | 0.9600 |
C9—O1—C8 | 116.9 (2) | O1—C9—C10 | 111.9 (2) |
C13—O4—C4 | 117.4 (2) | C16—C10—C11 | 120.3 (2) |
C23—O5—C24 | 116.5 (2) | C16—C10—C9 | 118.2 (2) |
N2—N1—C15 | 114.7 (2) | C11—C10—C9 | 121.5 (2) |
N1—N2—C17 | 114.1 (2) | C12—C11—C10 | 119.8 (2) |
C2—C1—H1A | 109.5 | C12—C11—H11 | 120.1 |
C2—C1—H1B | 109.5 | C10—C11—H11 | 120.1 |
H1A—C1—H1B | 109.5 | C14—C12—C11 | 119.7 (2) |
C2—C1—H1C | 109.5 | C14—C12—C13 | 119.1 (2) |
H1A—C1—H1C | 109.5 | C11—C12—C13 | 121.1 (2) |
H1B—C1—H1C | 109.5 | O3—C13—O4 | 123.8 (2) |
C3—C2—C1 | 131.1 (7) | O3—C13—C12 | 124.4 (3) |
C3—C2—H2A | 104.5 | O4—C13—C12 | 111.9 (2) |
C1—C2—H2A | 104.5 | C15—C14—C12 | 120.2 (2) |
C3—C2—H2B | 104.5 | C15—C14—H14 | 119.9 |
C1—C2—H2B | 104.5 | C12—C14—H14 | 119.9 |
H2A—C2—H2B | 105.6 | C14—C15—C16 | 120.4 (2) |
C2—C3—C4 | 132.1 (6) | C14—C15—N1 | 115.8 (2) |
C2—C3—H3A | 104.2 | C16—C15—N1 | 123.8 (2) |
C4—C3—H3A | 104.2 | C10—C16—C15 | 119.6 (2) |
C2—C3—H3B | 104.2 | C10—C16—H16 | 120.2 |
C4—C3—H3B | 104.2 | C15—C16—H16 | 120.2 |
H3A—C3—H3B | 105.5 | C22—C17—C18 | 119.8 (2) |
C3—C4—O4 | 108.9 (3) | C22—C17—N2 | 116.3 (2) |
C3—C4—H4A | 109.9 | C18—C17—N2 | 123.9 (2) |
O4—C4—H4A | 109.9 | C19—C18—C17 | 119.3 (2) |
C3—C4—H4B | 109.9 | C19—C18—H18 | 120.3 |
O4—C4—H4B | 109.9 | C17—C18—H18 | 120.3 |
H4A—C4—H4B | 108.3 | C18—C19—C20 | 121.1 (2) |
C6—C5—H5A | 109.5 | C18—C19—H19 | 119.4 |
C6—C5—H5B | 109.5 | C20—C19—H19 | 119.4 |
H5A—C5—H5B | 109.5 | C21—C20—C19 | 119.1 (2) |
C6—C5—H5C | 109.5 | C21—C20—C23 | 118.5 (2) |
H5A—C5—H5C | 109.5 | C19—C20—C23 | 122.4 (2) |
H5B—C5—H5C | 109.5 | C22—C21—C20 | 120.2 (2) |
C5—C6—C7 | 114.3 (6) | C22—C21—H21 | 119.9 |
C5—C6—H6A | 108.7 | C20—C21—H21 | 119.9 |
C7—C6—H6A | 108.7 | C21—C22—C17 | 120.5 (2) |
C5—C6—H6B | 108.7 | C21—C22—H22 | 119.7 |
C7—C6—H6B | 108.7 | C17—C22—H22 | 119.7 |
H6A—C6—H6B | 107.6 | O6—C23—O5 | 123.0 (3) |
C6—C7—C8 | 118.0 (4) | O6—C23—C20 | 124.8 (3) |
C6—C7—H7A | 107.8 | O5—C23—C20 | 112.2 (2) |
C8—C7—H7A | 107.8 | O5—C24—C25 | 108.2 (3) |
C6—C7—H7B | 107.8 | O5—C24—H24A | 110.1 |
C8—C7—H7B | 107.8 | C25—C24—H24A | 110.1 |
H7A—C7—H7B | 107.2 | O5—C24—H24B | 110.1 |
O1—C8—C7 | 107.9 (3) | C25—C24—H24B | 110.1 |
O1—C8—H8A | 110.1 | H24A—C24—H24B | 108.4 |
C7—C8—H8A | 110.1 | C24—C25—H25A | 109.5 |
O1—C8—H8B | 110.1 | C24—C25—H25B | 109.5 |
C7—C8—H8B | 110.1 | H25A—C25—H25B | 109.5 |
H8A—C8—H8B | 108.4 | C24—C25—H25C | 109.5 |
O2—C9—O1 | 124.2 (3) | H25A—C25—H25C | 109.5 |
O2—C9—C10 | 123.8 (3) | H25B—C25—H25C | 109.5 |
C15—N1—N2—C17 | 179.9 (2) | C12—C14—C15—N1 | 179.7 (2) |
C1—C2—C3—C4 | 175.9 (8) | N2—N1—C15—C14 | 176.5 (2) |
C2—C3—C4—O4 | 39.1 (12) | N2—N1—C15—C16 | −3.3 (4) |
C13—O4—C4—C3 | 166.9 (4) | C11—C10—C16—C15 | −2.1 (4) |
C5—C6—C7—C8 | −54.1 (7) | C9—C10—C16—C15 | 177.7 (2) |
C9—O1—C8—C7 | −165.9 (3) | C14—C15—C16—C10 | 1.9 (4) |
C6—C7—C8—O1 | −52.5 (5) | N1—C15—C16—C10 | −178.3 (2) |
C8—O1—C9—O2 | −1.0 (5) | N1—N2—C17—C22 | −172.5 (2) |
C8—O1—C9—C10 | 177.2 (3) | N1—N2—C17—C18 | 8.1 (4) |
O2—C9—C10—C16 | 10.6 (5) | C22—C17—C18—C19 | 0.3 (4) |
O1—C9—C10—C16 | −167.7 (2) | N2—C17—C18—C19 | 179.6 (2) |
O2—C9—C10—C11 | −169.7 (3) | C17—C18—C19—C20 | 0.5 (4) |
O1—C9—C10—C11 | 12.1 (4) | C18—C19—C20—C21 | −0.7 (4) |
C16—C10—C11—C12 | 0.8 (4) | C18—C19—C20—C23 | −178.8 (3) |
C9—C10—C11—C12 | −179.0 (3) | C19—C20—C21—C22 | 0.1 (4) |
C10—C11—C12—C14 | 0.7 (4) | C23—C20—C21—C22 | 178.2 (3) |
C10—C11—C12—C13 | −179.7 (2) | C20—C21—C22—C17 | 0.7 (5) |
C4—O4—C13—O3 | −0.4 (5) | C18—C17—C22—C21 | −0.9 (4) |
C4—O4—C13—C12 | −179.8 (3) | N2—C17—C22—C21 | 179.7 (3) |
C14—C12—C13—O3 | 6.7 (4) | C24—O5—C23—O6 | −1.3 (5) |
C11—C12—C13—O3 | −173.0 (3) | C24—O5—C23—C20 | 178.1 (2) |
C14—C12—C13—O4 | −174.0 (2) | C21—C20—C23—O6 | 5.3 (5) |
C11—C12—C13—O4 | 6.4 (4) | C19—C20—C23—O6 | −176.7 (3) |
C11—C12—C14—C15 | −0.9 (4) | C21—C20—C23—O5 | −174.1 (2) |
C13—C12—C14—C15 | 179.5 (2) | C19—C20—C23—O5 | 3.9 (4) |
C12—C14—C15—C16 | −0.5 (4) | C23—O5—C24—C25 | −178.6 (3) |
Experimental details
Crystal data | |
Chemical formula | C25H30N2O6 |
Mr | 454.51 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.675 (2), 11.299 (3), 13.636 (3) |
α, β, γ (°) | 97.311 (3), 94.806 (3), 109.793 (2) |
V (Å3) | 1235.8 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.12 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.990, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8643, 4275, 2736 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.218, 1.05 |
No. of reflections | 4275 |
No. of parameters | 302 |
No. of restraints | 13 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.32 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
Financial support from the National Natural Science Foundation of China (20501011) and Liaocheng University is gratefully acknowledged.
References
Bosman, A. W., Janssen, H. M. & Weijer, E. W. (1999). Chem. Rev. 99, 1665–1688. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tomalia, D. A., Naylor, A. M. & Goddard, W. A. (1990). Angew. Chem. Int. Ed. Engl. 29, 138–146. CrossRef Web of Science Google Scholar
Wang, S., Wang, X., Li, L. & Advincula, R. C. (2004). J. Org. Chem. 69, 9073–9084. Web of Science CSD CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Dendrimers have been the subject of intense investigation due to both interesting structural properties and promising applications in the areas of biological and material sciences (Tomalia et al., 1990; Bosman et al., 1999). Here, we describe the cystallization and structural characterization of the title compound.
As shown in Fig 1. the dihedral angle between the phenyl planes of the two benzene rings is 3.79 (1) Å. The mean deviations for the two phenyl planar are 0.0058 (1) and 0.0028 (1) Å, respectively. The C=O and C—O bond distances of carbonyl groups are 1.195 (3)—1.200 (3) and 1.324 (3)—1.452 (3) Å, respectively. The N=N and N—C bond distances are 1.240 (3) and 1.423 (3)—1.431 (3) Å, respectively, which are in the normal range compared to reported Dendrimer derivatives (Wang et al., 2004).