Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053901/om2180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053901/om2180Isup2.hkl |
CCDC reference: 672814
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.142
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C30 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C33
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.127 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.69 mm PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.48 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.55 Ratio PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 39.00 A 3
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
(I) was prepared a modification of literature method (Archer et al., 2006). A mixture of (I) (523 mg, 1 mmol) and sodium methacrylat (106 mg, 1 mmol) were refluxed in THF (20 ml) for 2 days and was concentrated (5 ml). Et2O was added with stirring to a final volume of 20 ml causing a yellow powder to precipitate. The precipitate was filtered off, washed with Et2O and dried. X-ray quality crystals were grown from CH2Cl2-hexane (1:2 v/v, 30 ml) (yield: 410 mg, 72%; m.p. 404–405 K). Analysis calculated for C35H42ClN3O2: C 73.47, H 7.40, N 7.34%; found: C 73.23, H 7.49, N 7.32%. 1H NMR (CDCl3): δ 8.32 (d, J = 8.0, 1H, py—Hm), 7.99 (d, J = 7.6, 1H, py—Hm), 7.94 (t, J = 7.6, 1H, py—Hp), 7.18–7.13 [m, 6H, (CH3)2CH—C6H3], 5.48 (s, 1H, CH2-acryl), 5.12 (s, 1H, CH2-acryl), 2.79–2.66 [m, 4H, (CH3)2CH—C6H3], 1.74 (s, 3H, CH3-acryl), 1.16–1.05 [m, 24H, (CH3)2CH—C6H3]; 13C NMR (CDCl3): δ 176.75, 168.33, 164.17, 159.49, 155.38, 149.27, 147.86, 145.28, 139.37, 136.14, 132.65; 130.29, 127.35, 126.03, 125.44, 118.14, 112.76, 29.91, 27.75, 22.44, 20.20.
H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.98, 0.96 and 0.93 Å for CH, CH3, aromatic CH and CH2 groups, respectively. The displacement parameters of the H atoms were constrained as Uiso(H) = 1.2Ueq (1.5Ueq for methyl) of the parent atom. Riding methyl H atoms were allowed to rotate freely during refinement using the AFIX 137 command of SHELXL97 (Sheldrick, 1997). Examination of the refined structure using PLATON (Spek, 2003) revealed the presence of void spaces having a total volume of 157.8 Å3 [4.8%] per unit cell, the volume of the individual voids being 39 Å3.
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
C35H42ClN3O2 | F(000) = 1224 |
Mr = 572.17 | Dx = 1.144 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 35523 reflections |
a = 9.4568 (3) Å | θ = 1.4–27.3° |
b = 14.6356 (7) Å | µ = 0.15 mm−1 |
c = 24.0095 (8) Å | T = 296 K |
β = 91.391 (3)° | Prism, colorless |
V = 3322.1 (2) Å3 | 0.69 × 0.58 × 0.30 mm |
Z = 4 |
STOE IPDS 2 diffractometer | 7398 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 4940 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.127 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.3°, θmin = 1.6° |
w scans | h = −12→12 |
Absorption correction: integration X-RED32 (Stoe & Cie, 2002) | k = −18→18 |
Tmin = 0.917, Tmax = 0.960 | l = −30→30 |
52993 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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0692P)2 + 0.1358P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
7398 reflections | Δρmax = 0.19 e Å−3 |
380 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0076 (10) |
C35H42ClN3O2 | V = 3322.1 (2) Å3 |
Mr = 572.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.4568 (3) Å | µ = 0.15 mm−1 |
b = 14.6356 (7) Å | T = 296 K |
c = 24.0095 (8) Å | 0.69 × 0.58 × 0.30 mm |
β = 91.391 (3)° |
STOE IPDS 2 diffractometer | 7398 independent reflections |
Absorption correction: integration X-RED32 (Stoe & Cie, 2002) | 4940 reflections with I > 2σ(I) |
Tmin = 0.917, Tmax = 0.960 | Rint = 0.127 |
52993 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.19 e Å−3 |
7398 reflections | Δρmin = −0.30 e Å−3 |
380 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 | ||
Cl1 | 0.09937 (5) | 0.11683 (5) | 0.130226 (18) | 0.0925 (2) | |
O1 | 0.09310 (12) | 0.09776 (10) | 0.38351 (4) | 0.0686 (3) | |
O2 | 0.39007 (13) | 0.20674 (11) | 0.25418 (6) | 0.0835 (4) | |
N1 | 0.01045 (12) | 0.14281 (9) | 0.24386 (5) | 0.0471 (3) | |
N2 | −0.16629 (14) | 0.16848 (10) | 0.11306 (5) | 0.0559 (3) | |
N3 | 0.24640 (12) | 0.14538 (9) | 0.31830 (5) | 0.0489 (3) | |
C1 | −0.01507 (14) | 0.13968 (10) | 0.29816 (5) | 0.0457 (3) | |
C2 | −0.14984 (15) | 0.13780 (12) | 0.31944 (6) | 0.0562 (4) | |
H2 | −0.1631 | 0.1347 | 0.3576 | 0.067* | |
C3 | −0.26403 (16) | 0.14068 (14) | 0.28249 (7) | 0.0646 (4) | |
H3 | −0.3560 | 0.1401 | 0.2954 | 0.078* | |
C4 | −0.23943 (16) | 0.14445 (12) | 0.22635 (6) | 0.0599 (4) | |
H4 | −0.3145 | 0.1468 | 0.2007 | 0.072* | |
C5 | −0.10126 (15) | 0.14471 (11) | 0.20865 (6) | 0.0483 (3) | |
C6 | −0.07281 (16) | 0.14728 (11) | 0.14799 (6) | 0.0532 (4) | |
C7 | −0.14697 (16) | 0.16956 (12) | 0.05439 (6) | 0.0560 (4) | |
C8 | −0.10439 (18) | 0.25004 (13) | 0.02938 (7) | 0.0632 (4) | |
C9 | −0.0905 (2) | 0.24901 (15) | −0.02835 (8) | 0.0747 (5) | |
H9 | −0.0597 | 0.3015 | −0.0462 | 0.090* | |
C10 | −0.1208 (2) | 0.17306 (16) | −0.05911 (7) | 0.0771 (5) | |
H10 | −0.1105 | 0.1742 | −0.0975 | 0.092* | |
C11 | −0.16686 (19) | 0.09442 (14) | −0.03359 (7) | 0.0694 (5) | |
H11 | −0.1886 | 0.0433 | −0.0551 | 0.083* | |
C12 | −0.18114 (17) | 0.09059 (12) | 0.02394 (6) | 0.0589 (4) | |
C13 | −0.0822 (2) | 0.33733 (15) | 0.06249 (8) | 0.0767 (5) | |
H13 | −0.0890 | 0.3212 | 0.1019 | 0.092* | |
C14 | −0.1990 (4) | 0.4046 (2) | 0.04950 (17) | 0.1455 (14) | |
H14A | −0.1831 | 0.4595 | 0.0706 | 0.218* | |
H14B | −0.2882 | 0.3784 | 0.0592 | 0.218* | |
H14C | −0.2002 | 0.4187 | 0.0104 | 0.218* | |
C15 | 0.0599 (3) | 0.3802 (2) | 0.05534 (16) | 0.1359 (11) | |
H15A | 0.1325 | 0.3359 | 0.0634 | 0.204* | |
H15B | 0.0705 | 0.4310 | 0.0804 | 0.204* | |
H15C | 0.0679 | 0.4011 | 0.0177 | 0.204* | |
C16 | −0.2335 (2) | 0.00589 (14) | 0.05299 (7) | 0.0694 (5) | |
H16 | −0.1710 | −0.0042 | 0.0856 | 0.083* | |
C17 | −0.2292 (2) | −0.08059 (15) | 0.01778 (9) | 0.0822 (6) | |
H17A | −0.2963 | −0.0755 | −0.0127 | 0.123* | |
H17B | −0.2527 | −0.1324 | 0.0403 | 0.123* | |
H17C | −0.1360 | −0.0884 | 0.0036 | 0.123* | |
C18 | −0.3825 (2) | 0.0218 (2) | 0.07462 (10) | 0.1040 (8) | |
H18A | −0.3843 | 0.0778 | 0.0954 | 0.156* | |
H18B | −0.4082 | −0.0281 | 0.0983 | 0.156* | |
H18C | −0.4486 | 0.0256 | 0.0437 | 0.156* | |
C19 | 0.10994 (15) | 0.12868 (11) | 0.33765 (6) | 0.0486 (3) | |
C20 | 0.28190 (16) | 0.21303 (12) | 0.28020 (7) | 0.0579 (4) | |
C21 | 0.19384 (17) | 0.29727 (13) | 0.27667 (8) | 0.0635 (4) | |
C22 | 0.1475 (2) | 0.33563 (15) | 0.32245 (10) | 0.0847 (6) | |
H22A | 0.1698 | 0.3101 | 0.3570 | 0.102* | |
H22B | 0.0925 | 0.3882 | 0.3202 | 0.102* | |
C23 | 0.1784 (2) | 0.33936 (17) | 0.21987 (10) | 0.0918 (7) | |
H23A | 0.1072 | 0.3071 | 0.1986 | 0.138* | |
H23B | 0.2669 | 0.3357 | 0.2013 | 0.138* | |
H23C | 0.1512 | 0.4023 | 0.2234 | 0.138* | |
C24 | 0.35683 (14) | 0.08216 (11) | 0.33730 (6) | 0.0514 (4) | |
C25 | 0.37940 (16) | 0.00325 (12) | 0.30608 (7) | 0.0603 (4) | |
C26 | 0.4819 (2) | −0.05741 (14) | 0.32601 (8) | 0.0748 (5) | |
H26 | 0.4983 | −0.1112 | 0.3066 | 0.090* | |
C27 | 0.5593 (2) | −0.03942 (15) | 0.37385 (8) | 0.0784 (5) | |
H27 | 0.6276 | −0.0808 | 0.3863 | 0.094* | |
C28 | 0.53648 (18) | 0.03889 (14) | 0.40326 (7) | 0.0694 (5) | |
H28 | 0.5908 | 0.0503 | 0.4353 | 0.083* | |
C29 | 0.43408 (15) | 0.10189 (12) | 0.38640 (6) | 0.0558 (4) | |
C30 | 0.41205 (17) | 0.18827 (13) | 0.41938 (7) | 0.0632 (4) | |
H30 | 0.3209 | 0.2145 | 0.4074 | 0.076* | |
C31 | 0.4057 (4) | 0.1689 (2) | 0.48191 (9) | 0.1244 (11) | |
H31A | 0.4974 | 0.1503 | 0.4957 | 0.187* | |
H31B | 0.3387 | 0.1210 | 0.4883 | 0.187* | |
H31C | 0.3770 | 0.2232 | 0.5010 | 0.187* | |
C32 | 0.5241 (3) | 0.2564 (2) | 0.40716 (16) | 0.1345 (12) | |
H32A | 0.6154 | 0.2297 | 0.4143 | 0.202* | |
H32B | 0.5129 | 0.3090 | 0.4305 | 0.202* | |
H32C | 0.5161 | 0.2744 | 0.3688 | 0.202* | |
C33 | 0.29733 (19) | −0.01790 (15) | 0.25266 (8) | 0.0737 (5) | |
H33 | 0.2347 | 0.0340 | 0.2445 | 0.088* | |
C34 | 0.2056 (4) | −0.1009 (3) | 0.26082 (17) | 0.1589 (15) | |
H34A | 0.2645 | −0.1531 | 0.2686 | 0.238* | |
H34B | 0.1498 | −0.1119 | 0.2276 | 0.238* | |
H34C | 0.1443 | −0.0907 | 0.2915 | 0.238* | |
C35 | 0.3943 (3) | −0.0290 (3) | 0.20401 (10) | 0.1347 (13) | |
H35A | 0.4535 | −0.0815 | 0.2100 | 0.202* | |
H35B | 0.4522 | 0.0246 | 0.2008 | 0.202* | |
H35C | 0.3387 | −0.0369 | 0.1704 | 0.202* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0634 (3) | 0.1692 (6) | 0.0451 (2) | 0.0331 (3) | 0.00353 (18) | −0.0044 (3) |
O1 | 0.0563 (6) | 0.1064 (10) | 0.0430 (6) | 0.0093 (6) | 0.0030 (4) | 0.0161 (6) |
O2 | 0.0544 (7) | 0.1148 (11) | 0.0822 (9) | 0.0067 (7) | 0.0181 (6) | 0.0299 (8) |
N1 | 0.0421 (6) | 0.0611 (7) | 0.0381 (6) | 0.0008 (5) | 0.0001 (4) | −0.0001 (5) |
N2 | 0.0548 (7) | 0.0726 (9) | 0.0401 (6) | −0.0004 (6) | −0.0028 (5) | 0.0022 (6) |
N3 | 0.0395 (6) | 0.0654 (8) | 0.0416 (6) | 0.0044 (5) | −0.0010 (4) | 0.0027 (5) |
C1 | 0.0421 (7) | 0.0565 (8) | 0.0385 (7) | 0.0017 (6) | 0.0004 (5) | 0.0004 (6) |
C2 | 0.0461 (7) | 0.0816 (11) | 0.0412 (7) | 0.0022 (7) | 0.0041 (6) | 0.0002 (7) |
C3 | 0.0407 (7) | 0.1008 (14) | 0.0525 (9) | −0.0005 (8) | 0.0038 (6) | 0.0018 (8) |
C4 | 0.0436 (7) | 0.0867 (12) | 0.0489 (8) | −0.0004 (7) | −0.0055 (6) | 0.0009 (8) |
C5 | 0.0466 (7) | 0.0592 (9) | 0.0387 (7) | 0.0007 (6) | −0.0025 (5) | −0.0001 (6) |
C6 | 0.0507 (8) | 0.0675 (10) | 0.0412 (7) | 0.0001 (7) | −0.0018 (6) | −0.0013 (6) |
C7 | 0.0513 (8) | 0.0770 (11) | 0.0395 (7) | 0.0052 (7) | −0.0044 (6) | 0.0030 (7) |
C8 | 0.0645 (9) | 0.0779 (12) | 0.0471 (9) | 0.0007 (8) | −0.0032 (7) | 0.0066 (8) |
C9 | 0.0806 (12) | 0.0917 (14) | 0.0518 (10) | 0.0041 (10) | 0.0025 (8) | 0.0185 (9) |
C10 | 0.0862 (13) | 0.1055 (16) | 0.0395 (8) | 0.0164 (11) | 0.0026 (8) | 0.0071 (9) |
C11 | 0.0728 (11) | 0.0901 (13) | 0.0449 (9) | 0.0129 (10) | −0.0040 (7) | −0.0050 (8) |
C12 | 0.0547 (8) | 0.0772 (11) | 0.0446 (8) | 0.0080 (8) | −0.0051 (6) | −0.0004 (7) |
C13 | 0.0839 (13) | 0.0801 (13) | 0.0657 (11) | −0.0125 (10) | −0.0071 (9) | 0.0064 (9) |
C14 | 0.122 (2) | 0.112 (2) | 0.200 (4) | 0.0292 (19) | −0.053 (2) | −0.067 (2) |
C15 | 0.098 (2) | 0.139 (3) | 0.170 (3) | −0.0331 (18) | −0.0128 (19) | −0.017 (2) |
C16 | 0.0714 (11) | 0.0835 (13) | 0.0530 (9) | −0.0095 (9) | −0.0034 (8) | −0.0004 (8) |
C17 | 0.0827 (13) | 0.0812 (13) | 0.0825 (14) | −0.0009 (11) | −0.0039 (10) | −0.0046 (10) |
C18 | 0.0911 (15) | 0.122 (2) | 0.1003 (17) | −0.0290 (14) | 0.0295 (13) | −0.0287 (15) |
C19 | 0.0445 (7) | 0.0635 (9) | 0.0378 (7) | 0.0056 (6) | 0.0016 (5) | 0.0014 (6) |
C20 | 0.0453 (8) | 0.0755 (11) | 0.0528 (8) | −0.0019 (7) | −0.0015 (6) | 0.0086 (8) |
C21 | 0.0506 (8) | 0.0660 (10) | 0.0732 (11) | −0.0072 (7) | −0.0093 (7) | 0.0122 (9) |
C22 | 0.0927 (15) | 0.0691 (12) | 0.0911 (15) | 0.0129 (11) | −0.0228 (11) | −0.0079 (11) |
C23 | 0.0740 (12) | 0.1016 (16) | 0.0997 (16) | −0.0031 (11) | −0.0011 (11) | 0.0470 (13) |
C24 | 0.0403 (7) | 0.0656 (9) | 0.0482 (8) | 0.0057 (6) | −0.0001 (6) | 0.0030 (7) |
C25 | 0.0486 (8) | 0.0730 (11) | 0.0593 (9) | 0.0068 (7) | 0.0017 (7) | −0.0054 (8) |
C26 | 0.0680 (11) | 0.0775 (12) | 0.0787 (12) | 0.0210 (9) | −0.0015 (9) | −0.0070 (10) |
C27 | 0.0665 (11) | 0.0895 (14) | 0.0788 (13) | 0.0285 (10) | −0.0066 (9) | 0.0053 (11) |
C28 | 0.0574 (9) | 0.0916 (13) | 0.0586 (10) | 0.0159 (9) | −0.0093 (7) | 0.0053 (9) |
C29 | 0.0463 (7) | 0.0745 (11) | 0.0466 (8) | 0.0061 (7) | −0.0016 (6) | 0.0027 (7) |
C30 | 0.0539 (9) | 0.0840 (12) | 0.0511 (9) | 0.0065 (8) | −0.0091 (7) | −0.0045 (8) |
C31 | 0.175 (3) | 0.145 (2) | 0.0532 (12) | 0.058 (2) | 0.0017 (14) | −0.0095 (13) |
C32 | 0.108 (2) | 0.107 (2) | 0.191 (3) | −0.0304 (16) | 0.042 (2) | −0.052 (2) |
C33 | 0.0630 (10) | 0.0879 (13) | 0.0697 (11) | 0.0122 (9) | −0.0074 (8) | −0.0244 (10) |
C34 | 0.153 (3) | 0.158 (3) | 0.163 (3) | −0.068 (3) | −0.055 (2) | −0.008 (2) |
C35 | 0.0994 (18) | 0.230 (4) | 0.0745 (15) | 0.033 (2) | −0.0008 (13) | −0.053 (2) |
Cl1—C6 | 1.7508 (16) | C17—H17B | 0.9600 |
O1—C19 | 1.2046 (17) | C17—H17C | 0.9600 |
O2—C20 | 1.2150 (19) | C18—H18A | 0.9600 |
N1—C1 | 1.3325 (17) | C18—H18B | 0.9600 |
N1—C5 | 1.3372 (17) | C18—H18C | 0.9600 |
N2—C6 | 1.2431 (19) | C20—C21 | 1.489 (3) |
N2—C7 | 1.4251 (19) | C21—C22 | 1.318 (3) |
N3—C20 | 1.395 (2) | C21—C23 | 1.500 (3) |
N3—C19 | 1.4035 (18) | C22—H22A | 0.9300 |
N3—C24 | 1.4599 (18) | C22—H22B | 0.9300 |
C1—C2 | 1.385 (2) | C23—H23A | 0.9600 |
C1—C19 | 1.5060 (18) | C23—H23B | 0.9600 |
C2—C3 | 1.382 (2) | C23—H23C | 0.9600 |
C2—H2 | 0.9300 | C24—C25 | 1.396 (2) |
C3—C4 | 1.374 (2) | C24—C29 | 1.402 (2) |
C3—H3 | 0.9300 | C25—C26 | 1.391 (2) |
C4—C5 | 1.384 (2) | C25—C33 | 1.515 (2) |
C4—H4 | 0.9300 | C26—C27 | 1.372 (3) |
C5—C6 | 1.488 (2) | C26—H26 | 0.9300 |
C7—C8 | 1.386 (2) | C27—C28 | 1.366 (3) |
C7—C12 | 1.401 (2) | C27—H27 | 0.9300 |
C8—C9 | 1.396 (2) | C28—C29 | 1.390 (2) |
C8—C13 | 1.517 (3) | C28—H28 | 0.9300 |
C9—C10 | 1.361 (3) | C29—C30 | 1.509 (2) |
C9—H9 | 0.9300 | C30—C32 | 1.489 (3) |
C10—C11 | 1.379 (3) | C30—C31 | 1.530 (3) |
C10—H10 | 0.9300 | C30—H30 | 0.9800 |
C11—C12 | 1.392 (2) | C31—H31A | 0.9600 |
C11—H11 | 0.9300 | C31—H31B | 0.9600 |
C12—C16 | 1.512 (3) | C31—H31C | 0.9600 |
C13—C15 | 1.497 (3) | C32—H32A | 0.9600 |
C13—C14 | 1.507 (4) | C32—H32B | 0.9600 |
C13—H13 | 0.9800 | C32—H32C | 0.9600 |
C14—H14A | 0.9600 | C33—C34 | 1.509 (4) |
C14—H14B | 0.9600 | C33—C35 | 1.511 (3) |
C14—H14C | 0.9600 | C33—H33 | 0.9800 |
C15—H15A | 0.9600 | C34—H34A | 0.9600 |
C15—H15B | 0.9600 | C34—H34B | 0.9600 |
C15—H15C | 0.9600 | C34—H34C | 0.9600 |
C16—C17 | 1.523 (3) | C35—H35A | 0.9600 |
C16—C18 | 1.532 (3) | C35—H35B | 0.9600 |
C16—H16 | 0.9800 | C35—H35C | 0.9600 |
C17—H17A | 0.9600 | ||
C1—N1—C5 | 117.40 (12) | H18A—C18—H18C | 109.5 |
C6—N2—C7 | 124.30 (14) | H18B—C18—H18C | 109.5 |
C20—N3—C19 | 125.35 (12) | O1—C19—N3 | 120.72 (12) |
C20—N3—C24 | 118.24 (12) | O1—C19—C1 | 119.76 (13) |
C19—N3—C24 | 116.28 (12) | N3—C19—C1 | 119.15 (12) |
N1—C1—C2 | 123.50 (13) | O2—C20—N3 | 120.17 (16) |
N1—C1—C19 | 117.49 (12) | O2—C20—C21 | 120.68 (16) |
C2—C1—C19 | 118.75 (12) | N3—C20—C21 | 118.82 (14) |
C3—C2—C1 | 118.32 (14) | C22—C21—C20 | 120.12 (17) |
C3—C2—H2 | 120.8 | C22—C21—C23 | 123.8 (2) |
C1—C2—H2 | 120.8 | C20—C21—C23 | 115.70 (18) |
C4—C3—C2 | 118.86 (14) | C21—C22—H22A | 120.0 |
C4—C3—H3 | 120.6 | C21—C22—H22B | 120.0 |
C2—C3—H3 | 120.6 | H22A—C22—H22B | 120.0 |
C3—C4—C5 | 119.01 (13) | C21—C23—H23A | 109.5 |
C3—C4—H4 | 120.5 | C21—C23—H23B | 109.5 |
C5—C4—H4 | 120.5 | H23A—C23—H23B | 109.5 |
N1—C5—C4 | 122.90 (13) | C21—C23—H23C | 109.5 |
N1—C5—C6 | 117.41 (12) | H23A—C23—H23C | 109.5 |
C4—C5—C6 | 119.69 (12) | H23B—C23—H23C | 109.5 |
N2—C6—C5 | 121.61 (14) | C25—C24—C29 | 122.59 (14) |
N2—C6—Cl1 | 123.33 (12) | C25—C24—N3 | 118.30 (13) |
C5—C6—Cl1 | 115.05 (10) | C29—C24—N3 | 119.10 (14) |
C8—C7—C12 | 122.73 (14) | C26—C25—C24 | 117.24 (15) |
C8—C7—N2 | 118.88 (15) | C26—C25—C33 | 119.96 (16) |
C12—C7—N2 | 118.25 (15) | C24—C25—C33 | 122.80 (15) |
C7—C8—C9 | 117.14 (17) | C27—C26—C25 | 121.23 (18) |
C7—C8—C13 | 121.79 (15) | C27—C26—H26 | 119.4 |
C9—C8—C13 | 120.96 (17) | C25—C26—H26 | 119.4 |
C10—C9—C8 | 121.60 (18) | C28—C27—C26 | 120.40 (17) |
C10—C9—H9 | 119.2 | C28—C27—H27 | 119.8 |
C8—C9—H9 | 119.2 | C26—C27—H27 | 119.8 |
C9—C10—C11 | 120.33 (16) | C27—C28—C29 | 121.56 (16) |
C9—C10—H10 | 119.8 | C27—C28—H28 | 119.2 |
C11—C10—H10 | 119.8 | C29—C28—H28 | 119.2 |
C10—C11—C12 | 120.90 (18) | C28—C29—C24 | 116.97 (16) |
C10—C11—H11 | 119.5 | C28—C29—C30 | 120.46 (14) |
C12—C11—H11 | 119.5 | C24—C29—C30 | 122.56 (14) |
C11—C12—C7 | 117.24 (17) | C32—C30—C29 | 110.45 (17) |
C11—C12—C16 | 122.11 (16) | C32—C30—C31 | 111.2 (2) |
C7—C12—C16 | 120.64 (14) | C29—C30—C31 | 111.64 (18) |
C15—C13—C14 | 111.0 (2) | C32—C30—H30 | 107.8 |
C15—C13—C8 | 114.0 (2) | C29—C30—H30 | 107.8 |
C14—C13—C8 | 110.51 (17) | C31—C30—H30 | 107.8 |
C15—C13—H13 | 107.0 | C30—C31—H31A | 109.5 |
C14—C13—H13 | 107.0 | C30—C31—H31B | 109.5 |
C8—C13—H13 | 107.0 | H31A—C31—H31B | 109.5 |
C13—C14—H14A | 109.5 | C30—C31—H31C | 109.5 |
C13—C14—H14B | 109.5 | H31A—C31—H31C | 109.5 |
H14A—C14—H14B | 109.5 | H31B—C31—H31C | 109.5 |
C13—C14—H14C | 109.5 | C30—C32—H32A | 109.5 |
H14A—C14—H14C | 109.5 | C30—C32—H32B | 109.5 |
H14B—C14—H14C | 109.5 | H32A—C32—H32B | 109.5 |
C13—C15—H15A | 109.5 | C30—C32—H32C | 109.5 |
C13—C15—H15B | 109.5 | H32A—C32—H32C | 109.5 |
H15A—C15—H15B | 109.5 | H32B—C32—H32C | 109.5 |
C13—C15—H15C | 109.5 | C34—C33—C35 | 112.1 (3) |
H15A—C15—H15C | 109.5 | C34—C33—C25 | 109.8 (2) |
H15B—C15—H15C | 109.5 | C35—C33—C25 | 111.61 (17) |
C12—C16—C17 | 114.32 (15) | C34—C33—H33 | 107.7 |
C12—C16—C18 | 110.27 (18) | C35—C33—H33 | 107.7 |
C17—C16—C18 | 110.57 (17) | C25—C33—H33 | 107.7 |
C12—C16—H16 | 107.1 | C33—C34—H34A | 109.5 |
C17—C16—H16 | 107.1 | C33—C34—H34B | 109.5 |
C18—C16—H16 | 107.1 | H34A—C34—H34B | 109.5 |
C16—C17—H17A | 109.5 | C33—C34—H34C | 109.5 |
C16—C17—H17B | 109.5 | H34A—C34—H34C | 109.5 |
H17A—C17—H17B | 109.5 | H34B—C34—H34C | 109.5 |
C16—C17—H17C | 109.5 | C33—C35—H35A | 109.5 |
H17A—C17—H17C | 109.5 | C33—C35—H35B | 109.5 |
H17B—C17—H17C | 109.5 | H35A—C35—H35B | 109.5 |
C16—C18—H18A | 109.5 | C33—C35—H35C | 109.5 |
C16—C18—H18B | 109.5 | H35A—C35—H35C | 109.5 |
H18A—C18—H18B | 109.5 | H35B—C35—H35C | 109.5 |
C16—C18—H18C | 109.5 | ||
C5—N1—C1—C2 | 0.4 (2) | C24—N3—C19—O1 | 33.8 (2) |
C5—N1—C1—C19 | 174.43 (13) | C20—N3—C19—C1 | 36.5 (2) |
N1—C1—C2—C3 | −1.0 (3) | C24—N3—C19—C1 | −139.26 (14) |
C19—C1—C2—C3 | −174.97 (16) | N1—C1—C19—O1 | −157.08 (15) |
C1—C2—C3—C4 | 0.6 (3) | C2—C1—C19—O1 | 17.3 (2) |
C2—C3—C4—C5 | 0.4 (3) | N1—C1—C19—N3 | 16.1 (2) |
C1—N1—C5—C4 | 0.6 (2) | C2—C1—C19—N3 | −169.59 (14) |
C1—N1—C5—C6 | −179.41 (13) | C19—N3—C20—O2 | −159.05 (16) |
C3—C4—C5—N1 | −1.0 (3) | C24—N3—C20—O2 | 16.6 (2) |
C3—C4—C5—C6 | 179.04 (16) | C19—N3—C20—C21 | 27.6 (2) |
C7—N2—C6—C5 | −178.02 (15) | C24—N3—C20—C21 | −156.76 (14) |
C7—N2—C6—Cl1 | 1.0 (2) | O2—C20—C21—C22 | −132.8 (2) |
N1—C5—C6—N2 | −164.47 (16) | N3—C20—C21—C22 | 40.5 (2) |
C4—C5—C6—N2 | 15.5 (2) | O2—C20—C21—C23 | 40.1 (2) |
N1—C5—C6—Cl1 | 16.44 (19) | N3—C20—C21—C23 | −146.60 (16) |
C4—C5—C6—Cl1 | −163.61 (13) | C20—N3—C24—C25 | −87.66 (18) |
C6—N2—C7—C8 | −91.8 (2) | C19—N3—C24—C25 | 88.37 (17) |
C6—N2—C7—C12 | 92.4 (2) | C20—N3—C24—C29 | 93.46 (17) |
C12—C7—C8—C9 | −2.7 (3) | C19—N3—C24—C29 | −90.50 (17) |
N2—C7—C8—C9 | −178.26 (15) | C29—C24—C25—C26 | 0.9 (2) |
C12—C7—C8—C13 | 173.73 (16) | N3—C24—C25—C26 | −177.90 (15) |
N2—C7—C8—C13 | −1.9 (2) | C29—C24—C25—C33 | −179.32 (16) |
C7—C8—C9—C10 | 1.7 (3) | N3—C24—C25—C33 | 1.9 (2) |
C13—C8—C9—C10 | −174.77 (18) | C24—C25—C26—C27 | −1.2 (3) |
C8—C9—C10—C11 | 0.1 (3) | C33—C25—C26—C27 | 179.06 (19) |
C9—C10—C11—C12 | −1.0 (3) | C25—C26—C27—C28 | 0.3 (3) |
C10—C11—C12—C7 | 0.0 (2) | C26—C27—C28—C29 | 0.8 (3) |
C10—C11—C12—C16 | 179.02 (17) | C27—C28—C29—C24 | −1.0 (3) |
C8—C7—C12—C11 | 1.9 (2) | C27—C28—C29—C30 | −179.43 (18) |
N2—C7—C12—C11 | 177.47 (14) | C25—C24—C29—C28 | 0.2 (2) |
C8—C7—C12—C16 | −177.16 (16) | N3—C24—C29—C28 | 178.97 (14) |
N2—C7—C12—C16 | −1.6 (2) | C25—C24—C29—C30 | 178.50 (15) |
C7—C8—C13—C15 | 126.6 (2) | N3—C24—C29—C30 | −2.7 (2) |
C9—C8—C13—C15 | −57.2 (3) | C28—C29—C30—C32 | 77.9 (3) |
C7—C8—C13—C14 | −107.6 (3) | C24—C29—C30—C32 | −100.4 (2) |
C9—C8—C13—C14 | 68.7 (3) | C28—C29—C30—C31 | −46.5 (2) |
C11—C12—C16—C17 | 16.3 (2) | C24—C29—C30—C31 | 135.2 (2) |
C7—C12—C16—C17 | −164.71 (16) | C26—C25—C33—C34 | 66.1 (3) |
C11—C12—C16—C18 | −108.98 (19) | C24—C25—C33—C34 | −113.6 (3) |
C7—C12—C16—C18 | 70.0 (2) | C26—C25—C33—C35 | −58.8 (3) |
C20—N3—C19—O1 | −150.47 (16) | C24—C25—C33—C35 | 121.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O1i | 0.96 | 2.45 | 3.392 (3) | 168 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C35H42ClN3O2 |
Mr | 572.17 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 9.4568 (3), 14.6356 (7), 24.0095 (8) |
β (°) | 91.391 (3) |
V (Å3) | 3322.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.69 × 0.58 × 0.30 |
Data collection | |
Diffractometer | STOE IPDS 2 diffractometer |
Absorption correction | Integration X-RED32 (Stoe & Cie, 2002) |
Tmin, Tmax | 0.917, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 52993, 7398, 4940 |
Rint | 0.127 |
(sin θ/λ)max (Å−1) | 0.644 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.142, 1.06 |
No. of reflections | 7398 |
No. of parameters | 380 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.30 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
Cl1—C6 | 1.7508 (16) | N3—C20 | 1.395 (2) |
O1—C19 | 1.2046 (17) | N3—C19 | 1.4035 (18) |
O2—C20 | 1.2150 (19) | N3—C24 | 1.4599 (18) |
N2—C6 | 1.2431 (19) | C1—C19 | 1.5060 (18) |
N2—C7 | 1.4251 (19) | C5—C6 | 1.488 (2) |
C6—N2—C7 | 124.30 (14) | C19—N3—C24 | 116.28 (12) |
C20—N3—C19 | 125.35 (12) | N2—C6—Cl1 | 123.33 (12) |
C20—N3—C24 | 118.24 (12) | C5—C6—Cl1 | 115.05 (10) |
C7—N2—C6—C5 | −178.02 (15) | C24—N3—C19—C1 | −139.26 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O1i | 0.96 | 2.45 | 3.392 (3) | 168.0 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Imide functionality is found as a basic structural element in a wide range of naturally occurring compounds such as uracil and thymine. Moreover, many imide-containing unnatural products have been prepared to test the pharmacological properties as well as their structural properties (Bacha et al., 1987; Sladowska et al., 1995). Imidoyl chlorides react with carboxylic acids and their salts, yielding N-substitue imides with regard to Mumm rearrangement reaction (Bonnett, 1970; Shishkin et al., 2004)
Proceeding with our research into pyridyl containing moties (Dayan & Çetinkaya, 2005), we have studied utility of the above reaction for preparing new functionally substituted pyridine derivatives. In this work, we synthesized (II) from N,N'-bis(2,6-diisopropylphenyl)pyridine-2,6-dicarboximidoyl dichloride, (I), with sodium methacrylat in THF. The title compound was characterized by elemental analysis, spectroscopic and X-ray crystallographic methods.
The structure of the title compound, (II), is shown in Fig. 1 and selected geometric parameters are listed in Table 1. The interatomic distances and angles show no anomalies. In the molecular structure of (II), (C7—C12) and (C24—C29) phenyl rings make dihedral angles of 72.72 (6) and 62.72 (6)°, respectively, with the pyridine ring.
In the crystal structure of (II), atom C14 in the molecule at (x, y, z) acts as hydrogen-bond donor to the O atom in the molecule at (-x, y + 1/2, -z + 1/2), forming a C(12) (Bernstein et al., 1995) chain running parallel to the [010] direction.