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The interaction between the peri substituents in the title compound, C18H18N2O2, measured at 150 K, represents an early stage in the addition reaction of an amino group to an electron-deficient alkene, and has an N...Csp2 separation of 2.531 (2) Å; comparison with related structures indicates that the nitrile group activates an alkene to nucleophilic attack more than a coplanar carboxyl­ic ester group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000512/fg1575sup1.cif
Contains datablocks global, V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000512/fg1575Vsup2.hkl
Contains datablock V

CCDC reference: 146048

Computing details top

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.

Ethyl E-2-Cyano-3-(8-dimethylaminonaphth-1-yl)propenoate top
Crystal data top
C18H18N2O2F(000) = 312
Mr = 294.34Dx = 1.267 Mg m3
Triclinic, P1Melting point = 335–337 K
a = 8.3856 (4) ÅMo Kα radiation, λ = 0.71069 Å
b = 9.7270 (4) ÅCell parameters from 11581 reflections
c = 11.1860 (5) Åθ = 2.6–23.7°
α = 69.274 (3)°µ = 0.08 mm1
β = 68.037 (3)°T = 150 K
γ = 70.933 (3)°Plate, yellow
V = 771.31 (6) Å30.3 × 0.3 × 0.1 mm
Z = 2
Data collection top
Enraf Nonius KappaCCD area detector
diffractometer
3134 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode2461 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 9.091 pixels mm-1θmax = 26.4°, θmin = 2.6°
φ and ω scans to fill Ewald sphereh = 1010
Absorption correction: multi-scan
using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995).
k = 1212
Tmin = 0.912, Tmax = 0.992l = 1313
11581 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053All H-atom parameters refined
wR(F2) = 0.158Calculated w = 1/[s2(Fo2) + ( 0.0865P)2 + 0.209P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.027
2939 reflectionsΔρmax = 0.56 e Å3
272 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL93 (Sheldrick, 1993), Fc*=kFc[1+0.001xFc2l3/sin(2q)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.053 (10)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8648 (2)0.11607 (14)0.29739 (12)0.0436 (4)
O20.7128 (2)0.34797 (14)0.31416 (12)0.0459 (4)
N10.7205 (2)0.3321 (2)0.67642 (14)0.0317 (4)
N20.7127 (3)0.1417 (2)0.5963 (2)0.0480 (5)
C10.6035 (2)0.2969 (2)0.8090 (2)0.0294 (4)
C20.6154 (3)0.3296 (2)0.9149 (2)0.0406 (5)
C30.4988 (3)0.2899 (2)1.0433 (2)0.0448 (5)
C40.3734 (3)0.2158 (2)1.0662 (2)0.0369 (4)
C50.2278 (2)0.1022 (2)0.9817 (2)0.0349 (4)
C60.2133 (2)0.0677 (2)0.8789 (2)0.0376 (4)
C70.3242 (2)0.1122 (2)0.7482 (2)0.0337 (4)
C80.4493 (2)0.1900 (2)0.7218 (2)0.0260 (4)
C90.3563 (2)0.1802 (2)0.9600 (2)0.0298 (4)
C100.4710 (2)0.2233 (2)0.82888 (15)0.0255 (4)
C110.5545 (2)0.2415 (2)0.5816 (2)0.0284 (4)
C120.6576 (2)0.1481 (2)0.5038 (2)0.0308 (4)
C130.6885 (2)0.0134 (2)0.5567 (2)0.0343 (4)
C140.7572 (2)0.1993 (2)0.3615 (2)0.0316 (4)
C150.8184 (3)0.4128 (2)0.1805 (2)0.0418 (5)
C160.9449 (3)0.4774 (3)0.1932 (2)0.0541 (6)
C180.8861 (3)0.2192 (3)0.6571 (2)0.0498 (5)
C190.7474 (3)0.4856 (2)0.6269 (2)0.0464 (5)
H20.711 (3)0.377 (3)0.900 (2)0.051 (6)*
H30.509 (3)0.310 (3)1.114 (3)0.057 (7)*
H40.299 (3)0.180 (2)1.153 (2)0.042 (5)*
H50.152 (3)0.073 (2)1.073 (2)0.049 (6)*
H60.124 (3)0.017 (3)0.890 (2)0.052 (6)*
H70.310 (3)0.090 (2)0.672 (2)0.042 (5)*
H110.539 (2)0.348 (2)0.541 (2)0.023 (4)*
H15A0.880 (3)0.328 (2)0.132 (2)0.049 (6)*
H15B0.735 (3)0.490 (2)0.133 (2)0.042 (5)*
H16A1.030 (4)0.389 (3)0.246 (3)0.067 (7)*
H16B0.880 (3)0.562 (3)0.248 (3)0.066 (7)*
H16C1.029 (4)0.528 (3)0.092 (3)0.086 (8)*
H18A0.953 (3)0.223 (2)0.709 (2)0.052 (6)*
H18B0.951 (3)0.248 (3)0.556 (3)0.063 (7)*
H18C0.860 (3)0.114 (3)0.688 (2)0.050 (6)*
H19A0.807 (3)0.502 (3)0.530 (3)0.059 (7)*
H19B0.824 (4)0.499 (3)0.667 (3)0.069 (8)*
H19C0.632 (4)0.558 (3)0.643 (2)0.058 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0498 (8)0.0374 (7)0.0308 (7)0.0050 (6)0.0024 (6)0.0137 (6)
O20.0474 (8)0.0319 (7)0.0300 (7)0.0001 (6)0.0069 (6)0.0029 (5)
N10.0247 (7)0.0321 (8)0.0348 (8)0.0059 (6)0.0059 (6)0.0083 (6)
N20.0693 (12)0.0335 (9)0.0318 (8)0.0105 (8)0.0035 (8)0.0105 (7)
C10.0285 (8)0.0255 (8)0.0319 (8)0.0016 (6)0.0086 (7)0.0094 (7)
C20.0419 (11)0.0421 (10)0.0449 (11)0.0080 (8)0.0161 (9)0.0174 (9)
C30.0550 (12)0.0484 (11)0.0363 (10)0.0026 (9)0.0179 (9)0.0207 (9)
C40.0430 (11)0.0354 (9)0.0237 (8)0.0009 (8)0.0073 (8)0.0092 (7)
C50.0309 (9)0.0338 (9)0.0272 (8)0.0057 (7)0.0009 (7)0.0049 (7)
C60.0304 (9)0.0407 (10)0.0388 (10)0.0147 (8)0.0008 (8)0.0110 (8)
C70.0311 (9)0.0390 (10)0.0313 (9)0.0095 (7)0.0046 (7)0.0129 (8)
C80.0242 (8)0.0253 (8)0.0242 (8)0.0014 (6)0.0042 (6)0.0085 (6)
C90.0299 (8)0.0257 (8)0.0257 (8)0.0017 (6)0.0063 (7)0.0067 (7)
C100.0246 (8)0.0219 (8)0.0249 (8)0.0009 (6)0.0058 (6)0.0073 (6)
C110.0267 (8)0.0294 (9)0.0260 (8)0.0050 (6)0.0058 (7)0.0070 (7)
C120.0319 (9)0.0294 (8)0.0258 (8)0.0057 (7)0.0043 (7)0.0068 (7)
C130.0417 (10)0.0329 (10)0.0226 (8)0.0075 (7)0.0013 (7)0.0101 (7)
C140.0318 (9)0.0299 (9)0.0272 (8)0.0034 (7)0.0049 (7)0.0079 (7)
C150.0438 (11)0.0332 (9)0.0282 (9)0.0045 (8)0.0017 (8)0.0018 (8)
C160.0516 (13)0.0590 (14)0.0446 (12)0.0128 (11)0.0065 (10)0.0131 (11)
C180.0323 (10)0.0551 (13)0.0499 (13)0.0015 (9)0.0090 (9)0.0137 (11)
C190.0481 (12)0.0423 (11)0.0484 (12)0.0202 (10)0.0120 (10)0.0045 (9)
Geometric parameters (Å, º) top
O1—C141.198 (2)C7—C81.374 (2)
O2—C141.328 (2)C8—C101.432 (2)
O2—C151.457 (2)C8—C111.478 (2)
N1—C11.432 (2)C9—C101.423 (2)
N1—C181.459 (2)C11—H110.96 (2)
N1—C191.459 (2)C11—C121.346 (2)
N2—C131.143 (2)C12—C131.441 (2)
C1—C21.376 (3)C12—C141.482 (2)
C1—C101.420 (2)C15—H15B1.00 (2)
C2—H20.98 (2)C15—H15A1.04 (2)
C2—C31.404 (3)C15—C161.467 (3)
C3—H30.92 (2)C16—H16A1.08 (3)
C3—C41.361 (3)C16—H16B1.08 (3)
C4—H40.95 (2)C16—H16C1.12 (3)
C4—C91.416 (2)C18—H18A0.96 (2)
C5—H50.98 (2)C18—H18C1.02 (2)
C5—C61.362 (3)C18—H18B1.03 (3)
C5—C91.415 (3)C19—H19B0.97 (3)
C6—H60.98 (2)C19—H19A0.98 (3)
C6—C71.410 (2)C19—H19C0.99 (3)
C7—H71.00 (2)
C14—O2—C15116.55 (14)H11—C11—C12117.9 (10)
C1—N1—C18112.84 (14)H11—C11—C8117.9 (10)
C1—N1—C19114.89 (15)C12—C11—C8123.80 (15)
C18—N1—C19112.5 (2)C11—C12—C13121.59 (15)
C2—C1—C10119.9 (2)C11—C12—C14124.16 (15)
C2—C1—N1123.3 (2)C13—C12—C14114.14 (14)
C10—C1—N1116.84 (14)N2—C13—C12178.6 (2)
H2—C2—C1118.6 (13)O1—C14—O2124.3 (2)
H2—C2—C3120.6 (13)O1—C14—C12123.8 (2)
C1—C2—C3120.7 (2)O2—C14—C12111.91 (14)
H3—C3—C4118.9 (15)H15B—C15—H15A108.0 (17)
H3—C3—C2120.2 (15)H15B—C15—O2106.9 (12)
C4—C3—C2120.8 (2)H15A—C15—O2107.8 (12)
H4—C4—C3122.7 (12)H15B—C15—C16112.8 (12)
H4—C4—C9116.9 (12)H15A—C15—C16112.6 (12)
C3—C4—C9120.3 (2)O2—C15—C16108.4 (2)
H5—C5—C6121.5 (13)H16A—C16—H16B108.0 (19)
H5—C5—C9117.8 (13)H16A—C16—H16C108 (2)
C6—C5—C9120.8 (2)H16B—C16—H16C109 (2)
H6—C6—C5123.0 (13)H16A—C16—C15109.0 (14)
H6—C6—C7116.7 (13)H16B—C16—C15112.1 (14)
C5—C6—C7120.3 (2)H16C—C16—C15110.6 (15)
H7—C7—C8119.0 (12)H18A—C18—H18C109.5 (18)
H7—C7—C6119.9 (12)H18A—C18—H18B111.4 (19)
C8—C7—C6121.1 (2)H18C—C18—H18B111.7 (19)
C7—C8—C10119.75 (15)H18A—C18—N1108.9 (13)
C7—C8—C11118.56 (15)H18C—C18—N1109.6 (13)
C10—C8—C11121.65 (14)H18B—C18—N1105.7 (14)
C5—C9—C4121.3 (2)H19B—C19—H19A108 (2)
C5—C9—C10119.5 (2)H19B—C19—H19C111 (2)
C4—C9—C10119.3 (2)H19A—C19—H19C110 (2)
C1—C10—C9118.99 (15)H19B—C19—N1111.9 (15)
C1—C10—C8122.37 (14)H19A—C19—N1106.2 (14)
C9—C10—C8118.64 (14)H19C—C19—N1109.4 (14)
Selected molecular geometry (Å, °) for (II), (III) and (V) top
(II)(III)(V)
N1···C112.413 (2)2.679 (2)2.531 (2)
C11-C121.354 (2)1.341 (2)1.346 (2)
N1-C1-C2124.3 (2)122.3 (2)123.3 (2)
N1-C1-C10115.9 (1)118.3 (2)116.8 (1)
C1-C10-C8120.4 (1)123.5 (2)122.4 (1)
C10-C8-C11120.2 (1)122.5 (2)121.7 (1)
C7-C8-C11120.3 (1)117.6 (2)118.6 (2)
N1-C11-C12112.5 (1)118.0 (1)114.4 (1)
C18-N1-C1-C2-81.5 (2)-105.0 (2)-82.9 (2)
C19-N1-C1-C249.2 (2)25.9 (3)47.9 (2)
 

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