Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000512/fg1575sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000512/fg1575Vsup2.hkl |
CCDC reference: 146048
Data collection: DENZO (Otinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL93.
C18H18N2O2 | F(000) = 312 |
Mr = 294.34 | Dx = 1.267 Mg m−3 |
Triclinic, P1 | Melting point = 335–337 K |
a = 8.3856 (4) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.7270 (4) Å | Cell parameters from 11581 reflections |
c = 11.1860 (5) Å | θ = 2.6–23.7° |
α = 69.274 (3)° | µ = 0.08 mm−1 |
β = 68.037 (3)° | T = 150 K |
γ = 70.933 (3)° | Plate, yellow |
V = 771.31 (6) Å3 | 0.3 × 0.3 × 0.1 mm |
Z = 2 |
Enraf Nonius KappaCCD area detector diffractometer | 3134 independent reflections |
Radiation source: Enraf-Nonius FR591 rotating anode | 2461 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 9.091 pixels mm-1 | θmax = 26.4°, θmin = 2.6° |
φ and ω scans to fill Ewald sphere | h = −10→10 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995). | k = −12→12 |
Tmin = 0.912, Tmax = 0.992 | l = −13→13 |
11581 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)] = 0.053 | All H-atom parameters refined |
wR(F2) = 0.158 | Calculated w = 1/[s2(Fo2) + ( 0.0865P)2 + 0.209P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = −0.027 |
2939 reflections | Δρmax = 0.56 e Å−3 |
272 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL93 (Sheldrick, 1993), Fc*=kFc[1+0.001xFc2l3/sin(2q)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.053 (10) |
Experimental. 1H NMR (CDCl3): 9.21 (1H, s, C=CH), 7.89 (1H, dd, J 7.3, 2.0), 7.66 (1H, dd, J 8.2, 0.9), 7.49 (3H, m), 7.35 (1H, dd, J 7.4, 1.0), 4.40 (2H, q, OCH2), 2.65 [6H, s, N(CH3)2], 1.41 (3H, t, CH3); 13C NMR (CDCl3): 163.5 (C=O), 161.2 (=CH), 150.1, 135.1, 130.8, 130.7, 129.8, 127.1, 126.7, 125.9, 125.3, 119.5, 115.7 (CN), 96.8 (=C(CN), 62.0 (OCH2), 45.3 [N(CH3)2], 14.3 (ester CH3); ν(cm-1): 2224, 1704, 1572, 1258, 1244, 1082, 834, 781, 766, 740, 619; HRMS: 294.1366, C18H18N2O2 requires 294.1368. |
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 on F2 for ALL reflections except for 195 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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 | 0.8648 (2) | 0.11607 (14) | 0.29739 (12) | 0.0436 (4) | |
O2 | 0.7128 (2) | 0.34797 (14) | 0.31416 (12) | 0.0459 (4) | |
N1 | 0.7205 (2) | 0.3321 (2) | 0.67642 (14) | 0.0317 (4) | |
N2 | 0.7127 (3) | −0.1417 (2) | 0.5963 (2) | 0.0480 (5) | |
C1 | 0.6035 (2) | 0.2969 (2) | 0.8090 (2) | 0.0294 (4) | |
C2 | 0.6154 (3) | 0.3296 (2) | 0.9149 (2) | 0.0406 (5) | |
C3 | 0.4988 (3) | 0.2899 (2) | 1.0433 (2) | 0.0448 (5) | |
C4 | 0.3734 (3) | 0.2158 (2) | 1.0662 (2) | 0.0369 (4) | |
C5 | 0.2278 (2) | 0.1022 (2) | 0.9817 (2) | 0.0349 (4) | |
C6 | 0.2133 (2) | 0.0677 (2) | 0.8789 (2) | 0.0376 (4) | |
C7 | 0.3242 (2) | 0.1122 (2) | 0.7482 (2) | 0.0337 (4) | |
C8 | 0.4493 (2) | 0.1900 (2) | 0.7218 (2) | 0.0260 (4) | |
C9 | 0.3563 (2) | 0.1802 (2) | 0.9600 (2) | 0.0298 (4) | |
C10 | 0.4710 (2) | 0.2233 (2) | 0.82888 (15) | 0.0255 (4) | |
C11 | 0.5545 (2) | 0.2415 (2) | 0.5816 (2) | 0.0284 (4) | |
C12 | 0.6576 (2) | 0.1481 (2) | 0.5038 (2) | 0.0308 (4) | |
C13 | 0.6885 (2) | −0.0134 (2) | 0.5567 (2) | 0.0343 (4) | |
C14 | 0.7572 (2) | 0.1993 (2) | 0.3615 (2) | 0.0316 (4) | |
C15 | 0.8184 (3) | 0.4128 (2) | 0.1805 (2) | 0.0418 (5) | |
C16 | 0.9449 (3) | 0.4774 (3) | 0.1932 (2) | 0.0541 (6) | |
C18 | 0.8861 (3) | 0.2192 (3) | 0.6571 (2) | 0.0498 (5) | |
C19 | 0.7474 (3) | 0.4856 (2) | 0.6269 (2) | 0.0464 (5) | |
H2 | 0.711 (3) | 0.377 (3) | 0.900 (2) | 0.051 (6)* | |
H3 | 0.509 (3) | 0.310 (3) | 1.114 (3) | 0.057 (7)* | |
H4 | 0.299 (3) | 0.180 (2) | 1.153 (2) | 0.042 (5)* | |
H5 | 0.152 (3) | 0.073 (2) | 1.073 (2) | 0.049 (6)* | |
H6 | 0.124 (3) | 0.017 (3) | 0.890 (2) | 0.052 (6)* | |
H7 | 0.310 (3) | 0.090 (2) | 0.672 (2) | 0.042 (5)* | |
H11 | 0.539 (2) | 0.348 (2) | 0.541 (2) | 0.023 (4)* | |
H15A | 0.880 (3) | 0.328 (2) | 0.132 (2) | 0.049 (6)* | |
H15B | 0.735 (3) | 0.490 (2) | 0.133 (2) | 0.042 (5)* | |
H16A | 1.030 (4) | 0.389 (3) | 0.246 (3) | 0.067 (7)* | |
H16B | 0.880 (3) | 0.562 (3) | 0.248 (3) | 0.066 (7)* | |
H16C | 1.029 (4) | 0.528 (3) | 0.092 (3) | 0.086 (8)* | |
H18A | 0.953 (3) | 0.223 (2) | 0.709 (2) | 0.052 (6)* | |
H18B | 0.951 (3) | 0.248 (3) | 0.556 (3) | 0.063 (7)* | |
H18C | 0.860 (3) | 0.114 (3) | 0.688 (2) | 0.050 (6)* | |
H19A | 0.807 (3) | 0.502 (3) | 0.530 (3) | 0.059 (7)* | |
H19B | 0.824 (4) | 0.499 (3) | 0.667 (3) | 0.069 (8)* | |
H19C | 0.632 (4) | 0.558 (3) | 0.643 (2) | 0.058 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0498 (8) | 0.0374 (7) | 0.0308 (7) | −0.0050 (6) | 0.0024 (6) | −0.0137 (6) |
O2 | 0.0474 (8) | 0.0319 (7) | 0.0300 (7) | −0.0001 (6) | 0.0069 (6) | −0.0029 (5) |
N1 | 0.0247 (7) | 0.0321 (8) | 0.0348 (8) | −0.0059 (6) | −0.0059 (6) | −0.0083 (6) |
N2 | 0.0693 (12) | 0.0335 (9) | 0.0318 (8) | −0.0105 (8) | −0.0035 (8) | −0.0105 (7) |
C1 | 0.0285 (8) | 0.0255 (8) | 0.0319 (8) | −0.0016 (6) | −0.0086 (7) | −0.0094 (7) |
C2 | 0.0419 (11) | 0.0421 (10) | 0.0449 (11) | −0.0080 (8) | −0.0161 (9) | −0.0174 (9) |
C3 | 0.0550 (12) | 0.0484 (11) | 0.0363 (10) | −0.0026 (9) | −0.0179 (9) | −0.0207 (9) |
C4 | 0.0430 (11) | 0.0354 (9) | 0.0237 (8) | 0.0009 (8) | −0.0073 (8) | −0.0092 (7) |
C5 | 0.0309 (9) | 0.0338 (9) | 0.0272 (8) | −0.0057 (7) | 0.0009 (7) | −0.0049 (7) |
C6 | 0.0304 (9) | 0.0407 (10) | 0.0388 (10) | −0.0147 (8) | −0.0008 (8) | −0.0110 (8) |
C7 | 0.0311 (9) | 0.0390 (10) | 0.0313 (9) | −0.0095 (7) | −0.0046 (7) | −0.0129 (8) |
C8 | 0.0242 (8) | 0.0253 (8) | 0.0242 (8) | −0.0014 (6) | −0.0042 (6) | −0.0085 (6) |
C9 | 0.0299 (8) | 0.0257 (8) | 0.0257 (8) | 0.0017 (6) | −0.0063 (7) | −0.0067 (7) |
C10 | 0.0246 (8) | 0.0219 (8) | 0.0249 (8) | 0.0009 (6) | −0.0058 (6) | −0.0073 (6) |
C11 | 0.0267 (8) | 0.0294 (9) | 0.0260 (8) | −0.0050 (6) | −0.0058 (7) | −0.0070 (7) |
C12 | 0.0319 (9) | 0.0294 (8) | 0.0258 (8) | −0.0057 (7) | −0.0043 (7) | −0.0068 (7) |
C13 | 0.0417 (10) | 0.0329 (10) | 0.0226 (8) | −0.0075 (7) | −0.0013 (7) | −0.0101 (7) |
C14 | 0.0318 (9) | 0.0299 (9) | 0.0272 (8) | −0.0034 (7) | −0.0049 (7) | −0.0079 (7) |
C15 | 0.0438 (11) | 0.0332 (9) | 0.0282 (9) | −0.0045 (8) | 0.0017 (8) | −0.0018 (8) |
C16 | 0.0516 (13) | 0.0590 (14) | 0.0446 (12) | −0.0128 (11) | −0.0065 (10) | −0.0131 (11) |
C18 | 0.0323 (10) | 0.0551 (13) | 0.0499 (13) | 0.0015 (9) | −0.0090 (9) | −0.0137 (11) |
C19 | 0.0481 (12) | 0.0423 (11) | 0.0484 (12) | −0.0202 (10) | −0.0120 (10) | −0.0045 (9) |
O1—C14 | 1.198 (2) | C7—C8 | 1.374 (2) |
O2—C14 | 1.328 (2) | C8—C10 | 1.432 (2) |
O2—C15 | 1.457 (2) | C8—C11 | 1.478 (2) |
N1—C1 | 1.432 (2) | C9—C10 | 1.423 (2) |
N1—C18 | 1.459 (2) | C11—H11 | 0.96 (2) |
N1—C19 | 1.459 (2) | C11—C12 | 1.346 (2) |
N2—C13 | 1.143 (2) | C12—C13 | 1.441 (2) |
C1—C2 | 1.376 (3) | C12—C14 | 1.482 (2) |
C1—C10 | 1.420 (2) | C15—H15B | 1.00 (2) |
C2—H2 | 0.98 (2) | C15—H15A | 1.04 (2) |
C2—C3 | 1.404 (3) | C15—C16 | 1.467 (3) |
C3—H3 | 0.92 (2) | C16—H16A | 1.08 (3) |
C3—C4 | 1.361 (3) | C16—H16B | 1.08 (3) |
C4—H4 | 0.95 (2) | C16—H16C | 1.12 (3) |
C4—C9 | 1.416 (2) | C18—H18A | 0.96 (2) |
C5—H5 | 0.98 (2) | C18—H18C | 1.02 (2) |
C5—C6 | 1.362 (3) | C18—H18B | 1.03 (3) |
C5—C9 | 1.415 (3) | C19—H19B | 0.97 (3) |
C6—H6 | 0.98 (2) | C19—H19A | 0.98 (3) |
C6—C7 | 1.410 (2) | C19—H19C | 0.99 (3) |
C7—H7 | 1.00 (2) | ||
C14—O2—C15 | 116.55 (14) | H11—C11—C12 | 117.9 (10) |
C1—N1—C18 | 112.84 (14) | H11—C11—C8 | 117.9 (10) |
C1—N1—C19 | 114.89 (15) | C12—C11—C8 | 123.80 (15) |
C18—N1—C19 | 112.5 (2) | C11—C12—C13 | 121.59 (15) |
C2—C1—C10 | 119.9 (2) | C11—C12—C14 | 124.16 (15) |
C2—C1—N1 | 123.3 (2) | C13—C12—C14 | 114.14 (14) |
C10—C1—N1 | 116.84 (14) | N2—C13—C12 | 178.6 (2) |
H2—C2—C1 | 118.6 (13) | O1—C14—O2 | 124.3 (2) |
H2—C2—C3 | 120.6 (13) | O1—C14—C12 | 123.8 (2) |
C1—C2—C3 | 120.7 (2) | O2—C14—C12 | 111.91 (14) |
H3—C3—C4 | 118.9 (15) | H15B—C15—H15A | 108.0 (17) |
H3—C3—C2 | 120.2 (15) | H15B—C15—O2 | 106.9 (12) |
C4—C3—C2 | 120.8 (2) | H15A—C15—O2 | 107.8 (12) |
H4—C4—C3 | 122.7 (12) | H15B—C15—C16 | 112.8 (12) |
H4—C4—C9 | 116.9 (12) | H15A—C15—C16 | 112.6 (12) |
C3—C4—C9 | 120.3 (2) | O2—C15—C16 | 108.4 (2) |
H5—C5—C6 | 121.5 (13) | H16A—C16—H16B | 108.0 (19) |
H5—C5—C9 | 117.8 (13) | H16A—C16—H16C | 108 (2) |
C6—C5—C9 | 120.8 (2) | H16B—C16—H16C | 109 (2) |
H6—C6—C5 | 123.0 (13) | H16A—C16—C15 | 109.0 (14) |
H6—C6—C7 | 116.7 (13) | H16B—C16—C15 | 112.1 (14) |
C5—C6—C7 | 120.3 (2) | H16C—C16—C15 | 110.6 (15) |
H7—C7—C8 | 119.0 (12) | H18A—C18—H18C | 109.5 (18) |
H7—C7—C6 | 119.9 (12) | H18A—C18—H18B | 111.4 (19) |
C8—C7—C6 | 121.1 (2) | H18C—C18—H18B | 111.7 (19) |
C7—C8—C10 | 119.75 (15) | H18A—C18—N1 | 108.9 (13) |
C7—C8—C11 | 118.56 (15) | H18C—C18—N1 | 109.6 (13) |
C10—C8—C11 | 121.65 (14) | H18B—C18—N1 | 105.7 (14) |
C5—C9—C4 | 121.3 (2) | H19B—C19—H19A | 108 (2) |
C5—C9—C10 | 119.5 (2) | H19B—C19—H19C | 111 (2) |
C4—C9—C10 | 119.3 (2) | H19A—C19—H19C | 110 (2) |
C1—C10—C9 | 118.99 (15) | H19B—C19—N1 | 111.9 (15) |
C1—C10—C8 | 122.37 (14) | H19A—C19—N1 | 106.2 (14) |
C9—C10—C8 | 118.64 (14) | H19C—C19—N1 | 109.4 (14) |
(II) | (III) | (V) | |
N1···C11 | 2.413 (2) | 2.679 (2) | 2.531 (2) |
C11-C12 | 1.354 (2) | 1.341 (2) | 1.346 (2) |
N1-C1-C2 | 124.3 (2) | 122.3 (2) | 123.3 (2) |
N1-C1-C10 | 115.9 (1) | 118.3 (2) | 116.8 (1) |
C1-C10-C8 | 120.4 (1) | 123.5 (2) | 122.4 (1) |
C10-C8-C11 | 120.2 (1) | 122.5 (2) | 121.7 (1) |
C7-C8-C11 | 120.3 (1) | 117.6 (2) | 118.6 (2) |
N1-C11-C12 | 112.5 (1) | 118.0 (1) | 114.4 (1) |
C18-N1-C1-C2 | -81.5 (2) | -105.0 (2) | -82.9 (2) |
C19-N1-C1-C2 | 49.2 (2) | 25.9 (3) | 47.9 (2) |
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