Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003016/ob6473sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003016/ob6473Isup2.hkl |
CCDC reference: 269834
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.004 Å
- R factor = 0.058
- wR factor = 0.124
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
Author Response: Our explanation of this problem is related to crystal size. Generally this type of compounds gives crystals with suitable size. However in some cases it is not possible to obtain crystals of appropriate size as in this case. Despite our efforts to grow crystals from different solvents only small samples were obtained. Considering the values of the rest of the structural parameters (displacement ellipsoids, R and Rw factors, GOOF etc.) we would like to submit the structure of this new compound with interesting properties in the present form. |
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.101 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 publication routines (Farrugia, 1999).
C21H22N2O2 | F(000) = 712 |
Mr = 334.41 | Dx = 1.187 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 22 reflections |
a = 8.711 (2) Å | θ = 16.6–17.5° |
b = 18.005 (3) Å | µ = 0.08 mm−1 |
c = 12.5175 (18) Å | T = 290 K |
β = 107.66 (2)° | Prism, red |
V = 1870.8 (6) Å3 | 0.26 × 0.20 × 0.14 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.101 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.1° |
Graphite monochromator | h = 0→10 |
non–profiled ω/2θ scans | k = −22→22 |
7703 measured reflections | l = −15→14 |
3674 independent reflections | 3 standard reflections every 500 reflections |
1433 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0338P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
3674 reflections | Δρmax = 0.15 e Å−3 |
227 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0076 (9) |
Experimental. The IR spectrum of (I) in solid state, shows 3 low intensity bands at 3076, 3054 and 3006 cm-1, belonging to νC—H of the aromatic ring and 8 stronger bands between 2960 and 2830 cm-1 for the aliphatic νC—H modes. There is no splitting of the very strong band at 2213 cm-1 attributed to the νCN vibration of the two cyano groups. The most prominent bands in the whole spectrum are at 1555 and 1504 cm-1. Together with the band at 1613 cm-1 they are assigned to the vibrations of the three conjugated double bonds. The νO—C vibration of the methoxy groups give rise to two intensive bands at 1164 and 1137 cm-1. The band assignment of the IR spectrum was performed by DFT/6–31 G* calculations |
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 | 0.5760 (4) | 0.40349 (18) | 0.6694 (3) | 0.0617 (9) | |
C2 | 0.4877 (4) | 0.38705 (16) | 0.7456 (3) | 0.0526 (8) | |
C3 | 0.5490 (4) | 0.32851 (19) | 0.8245 (3) | 0.0682 (10) | |
C4 | 0.3462 (3) | 0.42247 (15) | 0.7395 (2) | 0.0455 (8) | |
C5 | 0.2865 (3) | 0.48201 (14) | 0.6630 (2) | 0.0431 (7) | |
H5 | 0.3447 | 0.4961 | 0.6152 | 0.052* | |
C6 | 0.1487 (3) | 0.51893 (14) | 0.6570 (2) | 0.0398 (7) | |
C7 | 0.0480 (3) | 0.49624 (15) | 0.7302 (2) | 0.0489 (8) | |
H7A | −0.0360 | 0.4628 | 0.6882 | 0.059* | |
H7B | −0.0038 | 0.5400 | 0.7485 | 0.059* | |
C8 | 0.1435 (4) | 0.45825 (16) | 0.8384 (2) | 0.0498 (8) | |
C9 | 0.2467 (3) | 0.39732 (16) | 0.8115 (2) | 0.0554 (9) | |
H9A | 0.3178 | 0.3778 | 0.8812 | 0.066* | |
H9B | 0.1771 | 0.3572 | 0.7737 | 0.066* | |
C10 | 0.0231 (4) | 0.42371 (17) | 0.8926 (3) | 0.0763 (11) | |
H10A | 0.0811 | 0.3997 | 0.9615 | 0.114* | |
H10B | −0.0427 | 0.3879 | 0.8423 | 0.114* | |
H10C | −0.0442 | 0.4620 | 0.9076 | 0.114* | |
C11 | 0.2495 (4) | 0.51482 (17) | 0.9196 (2) | 0.0713 (10) | |
H11A | 0.3102 | 0.4900 | 0.9871 | 0.107* | |
H11B | 0.1825 | 0.5522 | 0.9375 | 0.107* | |
H11C | 0.3221 | 0.5377 | 0.8852 | 0.107* | |
C12 | 0.0995 (3) | 0.57965 (14) | 0.5807 (2) | 0.0448 (8) | |
H12 | 0.1658 | 0.5917 | 0.5373 | 0.054* | |
C13 | −0.0333 (3) | 0.62074 (15) | 0.5659 (2) | 0.0470 (8) | |
H13 | −0.1002 | 0.6069 | 0.6079 | 0.056* | |
C14 | −0.0859 (3) | 0.68417 (15) | 0.4925 (2) | 0.0449 (8) | |
C15 | 0.0124 (3) | 0.71609 (14) | 0.4339 (2) | 0.0471 (8) | |
H15 | 0.1151 | 0.6971 | 0.4438 | 0.057* | |
C16 | −0.0410 (4) | 0.77477 (15) | 0.3626 (3) | 0.0489 (8) | |
C17 | −0.1954 (4) | 0.80366 (15) | 0.3467 (3) | 0.0509 (8) | |
C18 | −0.2915 (3) | 0.77398 (16) | 0.4048 (3) | 0.0543 (8) | |
H18 | −0.3936 | 0.7935 | 0.3954 | 0.065* | |
C19 | −0.2366 (3) | 0.71503 (15) | 0.4773 (2) | 0.0526 (8) | |
H19 | −0.3024 | 0.6957 | 0.5168 | 0.063* | |
C20 | −0.3947 (4) | 0.89139 (18) | 0.2475 (3) | 0.0887 (12) | |
H20A | −0.4059 | 0.9320 | 0.1961 | 0.133* | |
H20B | −0.4140 | 0.9086 | 0.3149 | 0.133* | |
H20C | −0.4713 | 0.8534 | 0.2138 | 0.133* | |
C21 | 0.1976 (4) | 0.77987 (18) | 0.3079 (3) | 0.0785 (11) | |
H21A | 0.2456 | 0.8094 | 0.2627 | 0.118* | |
H21B | 0.1836 | 0.7299 | 0.2798 | 0.118* | |
H21C | 0.2664 | 0.7798 | 0.3841 | 0.118* | |
N1 | 0.6435 (4) | 0.41579 (17) | 0.6062 (3) | 0.0906 (11) | |
N2 | 0.5966 (4) | 0.28184 (18) | 0.8869 (3) | 0.1025 (12) | |
O1 | −0.2362 (3) | 0.86200 (11) | 0.27389 (19) | 0.0703 (7) | |
O2 | 0.0456 (2) | 0.81018 (10) | 0.30362 (18) | 0.0674 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.054 (2) | 0.062 (2) | 0.071 (2) | 0.0107 (18) | 0.023 (2) | −0.0035 (19) |
C2 | 0.051 (2) | 0.054 (2) | 0.052 (2) | 0.0095 (17) | 0.0145 (17) | 0.0007 (16) |
C3 | 0.067 (3) | 0.070 (2) | 0.068 (3) | 0.024 (2) | 0.021 (2) | 0.006 (2) |
C4 | 0.050 (2) | 0.0445 (17) | 0.0428 (19) | −0.0037 (16) | 0.0146 (17) | −0.0061 (15) |
C5 | 0.0424 (19) | 0.0467 (18) | 0.0433 (18) | −0.0002 (15) | 0.0173 (15) | −0.0006 (15) |
C6 | 0.0412 (18) | 0.0399 (16) | 0.0365 (17) | −0.0022 (15) | 0.0090 (15) | −0.0025 (14) |
C7 | 0.0439 (19) | 0.0569 (19) | 0.0490 (19) | 0.0034 (15) | 0.0187 (15) | 0.0074 (15) |
C8 | 0.056 (2) | 0.0506 (18) | 0.0477 (19) | 0.0040 (17) | 0.0237 (16) | 0.0067 (16) |
C9 | 0.059 (2) | 0.0535 (19) | 0.056 (2) | 0.0066 (16) | 0.0208 (18) | 0.0115 (16) |
C10 | 0.079 (3) | 0.086 (3) | 0.076 (3) | 0.013 (2) | 0.041 (2) | 0.027 (2) |
C11 | 0.078 (3) | 0.085 (2) | 0.052 (2) | 0.006 (2) | 0.0211 (19) | −0.0055 (19) |
C12 | 0.047 (2) | 0.0462 (18) | 0.0430 (18) | −0.0008 (16) | 0.0159 (16) | −0.0019 (15) |
C13 | 0.048 (2) | 0.0503 (19) | 0.0409 (18) | −0.0054 (16) | 0.0113 (16) | 0.0001 (15) |
C14 | 0.0451 (19) | 0.0450 (18) | 0.0441 (19) | 0.0002 (15) | 0.0125 (16) | −0.0013 (15) |
C15 | 0.0437 (18) | 0.0428 (17) | 0.055 (2) | 0.0078 (15) | 0.0150 (17) | 0.0036 (16) |
C16 | 0.048 (2) | 0.0408 (18) | 0.062 (2) | 0.0056 (16) | 0.0221 (17) | 0.0059 (16) |
C17 | 0.051 (2) | 0.0413 (18) | 0.058 (2) | 0.0081 (16) | 0.0143 (18) | 0.0061 (16) |
C18 | 0.0413 (19) | 0.053 (2) | 0.067 (2) | 0.0117 (16) | 0.0156 (18) | 0.0050 (17) |
C19 | 0.046 (2) | 0.0532 (19) | 0.062 (2) | 0.0010 (17) | 0.0223 (18) | 0.0048 (17) |
C20 | 0.063 (2) | 0.077 (2) | 0.124 (3) | 0.031 (2) | 0.025 (2) | 0.033 (2) |
C21 | 0.064 (2) | 0.086 (3) | 0.102 (3) | 0.022 (2) | 0.049 (2) | 0.035 (2) |
N1 | 0.071 (2) | 0.103 (2) | 0.111 (3) | 0.0118 (19) | 0.048 (2) | 0.005 (2) |
N2 | 0.099 (3) | 0.103 (3) | 0.101 (3) | 0.043 (2) | 0.022 (2) | 0.030 (2) |
O1 | 0.0570 (15) | 0.0604 (14) | 0.0964 (18) | 0.0221 (12) | 0.0276 (13) | 0.0281 (13) |
O2 | 0.0579 (15) | 0.0640 (14) | 0.0906 (17) | 0.0193 (12) | 0.0381 (14) | 0.0330 (13) |
C1—N1 | 1.142 (4) | C11—H11C | 0.9600 |
C1—C2 | 1.426 (4) | C12—C13 | 1.338 (3) |
C2—C4 | 1.369 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.432 (4) | C13—C14 | 1.450 (4) |
C3—N2 | 1.137 (4) | C13—H13 | 0.9300 |
C4—C5 | 1.426 (4) | C14—C19 | 1.384 (4) |
C4—C9 | 1.498 (4) | C14—C15 | 1.408 (3) |
C5—C6 | 1.354 (3) | C15—C16 | 1.370 (3) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—C12 | 1.430 (3) | C16—O2 | 1.363 (3) |
C6—C7 | 1.503 (3) | C16—C17 | 1.399 (4) |
C7—C8 | 1.520 (4) | C17—O1 | 1.365 (3) |
C7—H7A | 0.9700 | C17—C18 | 1.373 (4) |
C7—H7B | 0.9700 | C18—C19 | 1.384 (4) |
C8—C9 | 1.519 (4) | C18—H18 | 0.9300 |
C8—C11 | 1.534 (4) | C19—H19 | 0.9300 |
C8—C10 | 1.543 (4) | C20—O1 | 1.421 (3) |
C9—H9A | 0.9700 | C20—H20A | 0.9600 |
C9—H9B | 0.9700 | C20—H20B | 0.9600 |
C10—H10A | 0.9600 | C20—H20C | 0.9600 |
C10—H10B | 0.9600 | C21—O2 | 1.418 (3) |
C10—H10C | 0.9600 | C21—H21A | 0.9600 |
C11—H11A | 0.9600 | C21—H21B | 0.9600 |
C11—H11B | 0.9600 | C21—H21C | 0.9600 |
N1—C1—C2 | 178.2 (4) | C8—C11—H11C | 109.5 |
C4—C2—C1 | 121.7 (3) | H11A—C11—H11C | 109.5 |
C4—C2—C3 | 121.5 (3) | H11B—C11—H11C | 109.5 |
C1—C2—C3 | 116.7 (3) | C13—C12—C6 | 125.9 (3) |
N2—C3—C2 | 179.5 (4) | C13—C12—H12 | 117.0 |
C2—C4—C5 | 121.8 (3) | C6—C12—H12 | 117.0 |
C2—C4—C9 | 120.1 (3) | C12—C13—C14 | 128.1 (3) |
C5—C4—C9 | 118.1 (3) | C12—C13—H13 | 116.0 |
C6—C5—C4 | 122.9 (3) | C14—C13—H13 | 116.0 |
C6—C5—H5 | 118.6 | C19—C14—C15 | 117.8 (3) |
C4—C5—H5 | 118.6 | C19—C14—C13 | 120.4 (3) |
C5—C6—C12 | 119.5 (3) | C15—C14—C13 | 121.8 (3) |
C5—C6—C7 | 120.3 (2) | C16—C15—C14 | 120.9 (3) |
C12—C6—C7 | 120.2 (3) | C16—C15—H15 | 119.5 |
C6—C7—C8 | 113.7 (2) | C14—C15—H15 | 119.5 |
C6—C7—H7A | 108.8 | O2—C16—C15 | 125.4 (3) |
C8—C7—H7A | 108.8 | O2—C16—C17 | 114.5 (3) |
C6—C7—H7B | 108.8 | C15—C16—C17 | 120.1 (3) |
C8—C7—H7B | 108.8 | O1—C17—C18 | 125.2 (3) |
H7A—C7—H7B | 107.7 | O1—C17—C16 | 115.2 (3) |
C9—C8—C7 | 109.2 (2) | C18—C17—C16 | 119.6 (3) |
C9—C8—C11 | 110.4 (3) | C17—C18—C19 | 120.1 (3) |
C7—C8—C11 | 110.4 (2) | C17—C18—H18 | 120.0 |
C9—C8—C10 | 109.5 (2) | C19—C18—H18 | 120.0 |
C7—C8—C10 | 108.2 (2) | C14—C19—C18 | 121.5 (3) |
C11—C8—C10 | 109.2 (3) | C14—C19—H19 | 119.3 |
C4—C9—C8 | 113.8 (2) | C18—C19—H19 | 119.3 |
C4—C9—H9A | 108.8 | O1—C20—H20A | 109.5 |
C8—C9—H9A | 108.8 | O1—C20—H20B | 109.5 |
C4—C9—H9B | 108.8 | H20A—C20—H20B | 109.5 |
C8—C9—H9B | 108.8 | O1—C20—H20C | 109.5 |
H9A—C9—H9B | 107.7 | H20A—C20—H20C | 109.5 |
C8—C10—H10A | 109.5 | H20B—C20—H20C | 109.5 |
C8—C10—H10B | 109.5 | O2—C21—H21A | 109.5 |
H10A—C10—H10B | 109.5 | O2—C21—H21B | 109.5 |
C8—C10—H10C | 109.5 | H21A—C21—H21B | 109.5 |
H10A—C10—H10C | 109.5 | O2—C21—H21C | 109.5 |
H10B—C10—H10C | 109.5 | H21A—C21—H21C | 109.5 |
C8—C11—H11A | 109.5 | H21B—C21—H21C | 109.5 |
C8—C11—H11B | 109.5 | C17—O1—C20 | 118.7 (2) |
H11A—C11—H11B | 109.5 | C16—O2—C21 | 117.6 (2) |
C3—C2—C4—C5 | 178.5 (3) | C13—C14—C15—C16 | 178.3 (2) |
C4—C5—C6—C12 | 177.9 (2) | C15—C16—C17—O1 | −180.0 (3) |
C6—C12—C13—C14 | 177.8 (3) | C16—C17—O1—C20 | 175.9 (3) |