Literature DB >> 21754395

2-(4-Meth-oxy-benz-yl)-4,6-diphenyl-2,5-diaza-bicyclo-[2.2.2]oct-5-en-3-one.

Jo Alen, Liliana Dobrzańska, Luc Van Meervelt, Wim M De Borggraeve.   

Abstract

In the crystal structure of the title compound, C(26)H(24)N(2)O(2), weak inter-molecular C-H⋯π inter-actions involving the benzene of the p-methoxy benzyl group and one of the phenyl rings result in the formation of chains consisting of alternating enanti-omers. Weak C-H ⋯O inter-actions with the methoxy O atom lead to the formation of layers, which are inter-linked by further C-H⋯O inter-actions into a three-dimensional assembly.

Entities:  

Year:  2011        PMID： 21754395      PMCID： PMC3089292          DOI： 10.1107/S1600536811012165

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For our studies on pyrazinone chemistry, see: De Borggraeve et al. (2004 ▶); Azzam et al. (2004 ▶); Alen et al. (2007a ▶); Rombouts et al. (2003 ▶). For a crystal structure with a 2,5-diaza­bicyclo­[2.2.2]oct-5-en-3-one core, see: Rusinov et al. (2009 ▶). For crystal structures with a similar 2,5-diaza­bicyclo­[2.2.2]octane-3,6-dione core, see: Alen et al. (2007b ▶); Holl et al. (2008 ▶).

Experimental

Crystal data

C26H24N2O2 M = 396.47 Triclinic, a = 6.2770 (1) Å b = 11.5684 (2) Å c = 14.1443 (2) Å α = 85.497 (1)° β = 89.900 (1)° γ = 76.144 (1)° V = 993.97 (3) Å3 Z = 2 Cu Kα radiation μ = 0.67 mm−1 T = 100 K 0.34 × 0.18 × 0.15 mm

Data collection

Bruker SMART 6000 diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.805, T max = 0.907 10093 measured reflections 3473 independent reflections 2894 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.105 S = 1.05 3473 reflections 272 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.27 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012165/hg5019sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012165/hg5019Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H24N2O2Z = 2
Mr = 396.47F(000) = 420
Triclinic, P1Dx = 1.325 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 6.2770 (1) ÅCell parameters from 3657 reflections
b = 11.5684 (2) Åθ = 4.0–68.4°
c = 14.1443 (2) ŵ = 0.67 mm−1
α = 85.497 (1)°T = 100 K
β = 89.900 (1)°Block, colorless
γ = 76.144 (1)°0.34 × 0.18 × 0.15 mm
V = 993.97 (3) Å3
Bruker SMART 6000 diffractometer3473 independent reflections
Radiation source: fine-focus sealed tube2894 reflections with I > 2σ(I)
crossed Göbel mirrorsRint = 0.028
ω and φ scansθmax = 68.5°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −7→7
Tmin = 0.805, Tmax = 0.907k = −13→13
10093 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0591P)2 + 0.2042P] where P = (Fo2 + 2Fc2)/3
3473 reflections(Δ/σ)max < 0.001
272 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
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.
xyzUiso*/Ueq
C10.3365 (2)0.39618 (12)0.79614 (10)0.0184 (3)
H10.44520.32530.77470.022*
N20.30988 (19)0.50050 (10)0.72762 (8)0.0182 (3)
C30.1528 (2)0.59721 (12)0.74710 (9)0.0169 (3)
C40.0393 (2)0.57044 (12)0.84081 (9)0.0162 (3)
N5−0.04137 (19)0.46034 (10)0.83215 (8)0.0167 (3)
C60.1113 (2)0.37223 (12)0.80940 (9)0.0167 (3)
C70.2259 (2)0.54041 (12)0.91838 (9)0.0181 (3)
H7B0.29070.60990.92260.022*
H7A0.16450.52270.98090.022*
C80.4036 (2)0.43205 (13)0.89272 (10)0.0195 (3)
H8A0.41500.36510.94200.023*
H8B0.54770.45270.88810.023*
C9−0.1499 (2)0.67346 (12)0.86188 (10)0.0170 (3)
C10−0.1369 (3)0.74953 (13)0.93157 (10)0.0242 (3)
H10−0.00420.73840.96700.029*
C11−0.3152 (3)0.84182 (13)0.95039 (11)0.0278 (4)
H11−0.30410.89200.99920.033*
C12−0.5084 (3)0.86085 (13)0.89838 (11)0.0252 (3)
H12−0.63010.92390.91130.030*
C13−0.5227 (2)0.78717 (13)0.82731 (11)0.0252 (3)
H13−0.65420.80000.79070.030*
C14−0.3449 (2)0.69462 (12)0.80964 (11)0.0219 (3)
H14−0.35660.64450.76080.026*
C150.0681 (2)0.25323 (12)0.79874 (10)0.0184 (3)
C16−0.1056 (2)0.22043 (12)0.84705 (10)0.0200 (3)
H16−0.19340.27410.88720.024*
C17−0.1512 (2)0.11049 (13)0.83698 (11)0.0256 (3)
H17−0.26890.08890.87050.031*
C18−0.0242 (3)0.03196 (13)0.77777 (12)0.0282 (4)
H18−0.0539−0.04390.77140.034*
C190.1452 (3)0.06430 (13)0.72808 (11)0.0273 (4)
H190.22910.01160.68620.033*
C200.1933 (2)0.17386 (13)0.73923 (10)0.0230 (3)
H200.31220.19470.70610.028*
C210.4620 (2)0.49909 (13)0.64896 (10)0.0200 (3)
H21B0.61100.49350.67460.024*
H21A0.41680.57500.60860.024*
C220.4685 (2)0.39600 (12)0.58928 (9)0.0185 (3)
C230.2800 (2)0.38246 (12)0.54412 (10)0.0200 (3)
H230.14500.43910.55160.024*
C240.2841 (2)0.28809 (12)0.48822 (10)0.0206 (3)
H240.15340.28000.45840.025*
C250.4826 (2)0.20556 (12)0.47653 (10)0.0204 (3)
C260.6727 (2)0.21824 (13)0.52098 (10)0.0215 (3)
H260.80820.16240.51280.026*
C270.6647 (2)0.31205 (13)0.57704 (10)0.0204 (3)
H270.79500.31930.60760.024*
O280.50771 (17)0.10994 (9)0.42322 (7)0.0259 (3)
C290.3127 (3)0.08362 (14)0.38884 (12)0.0289 (4)
H29B0.21930.07100.44240.043*
H29C0.35140.01120.35470.043*
H29A0.23340.15060.34580.043*
O300.10832 (16)0.69324 (8)0.69944 (7)0.0208 (2)
U11U22U33U12U13U23
C10.0169 (7)0.0183 (7)0.0186 (7)−0.0017 (5)0.0005 (5)−0.0013 (5)
N20.0193 (6)0.0193 (6)0.0159 (6)−0.0043 (5)0.0026 (5)−0.0015 (5)
C30.0166 (7)0.0202 (7)0.0155 (7)−0.0064 (5)−0.0013 (5)−0.0041 (5)
C40.0177 (7)0.0169 (7)0.0151 (7)−0.0060 (5)−0.0002 (5)−0.0025 (5)
N50.0178 (6)0.0171 (6)0.0156 (6)−0.0047 (5)−0.0003 (4)−0.0018 (4)
C60.0178 (7)0.0186 (7)0.0126 (6)−0.0026 (5)−0.0012 (5)0.0002 (5)
C70.0174 (7)0.0235 (7)0.0142 (7)−0.0069 (6)−0.0005 (5)−0.0010 (5)
C80.0170 (8)0.0245 (7)0.0169 (7)−0.0054 (6)−0.0006 (5)0.0002 (6)
C90.0189 (8)0.0159 (7)0.0171 (7)−0.0065 (5)0.0026 (5)0.0001 (5)
C100.0262 (8)0.0232 (8)0.0229 (8)−0.0042 (6)−0.0026 (6)−0.0045 (6)
C110.0383 (10)0.0211 (8)0.0228 (8)−0.0030 (6)−0.0013 (7)−0.0077 (6)
C120.0263 (8)0.0164 (7)0.0304 (8)−0.0001 (6)0.0059 (6)−0.0030 (6)
C130.0192 (8)0.0201 (7)0.0363 (9)−0.0044 (6)−0.0024 (6)−0.0030 (6)
C140.0225 (8)0.0173 (7)0.0268 (8)−0.0049 (6)−0.0013 (6)−0.0070 (6)
C150.0187 (8)0.0172 (7)0.0177 (7)−0.0015 (5)−0.0055 (5)−0.0004 (5)
C160.0176 (8)0.0190 (7)0.0225 (7)−0.0023 (5)−0.0050 (5)−0.0021 (6)
C170.0198 (8)0.0238 (8)0.0333 (8)−0.0064 (6)−0.0054 (6)0.0003 (6)
C180.0304 (9)0.0172 (7)0.0365 (9)−0.0043 (6)−0.0121 (7)−0.0033 (6)
C190.0312 (9)0.0199 (7)0.0274 (8)0.0024 (6)−0.0051 (6)−0.0074 (6)
C200.0232 (8)0.0208 (7)0.0225 (7)−0.0004 (6)−0.0017 (6)−0.0013 (6)
C210.0198 (8)0.0227 (7)0.0189 (7)−0.0074 (6)0.0040 (5)−0.0034 (6)
C220.0214 (8)0.0212 (7)0.0140 (7)−0.0074 (6)0.0023 (5)0.0002 (5)
C230.0190 (8)0.0207 (7)0.0196 (7)−0.0034 (6)0.0018 (5)−0.0006 (6)
C240.0209 (8)0.0230 (7)0.0193 (7)−0.0082 (6)−0.0012 (6)−0.0005 (6)
C250.0268 (8)0.0184 (7)0.0171 (7)−0.0075 (6)0.0019 (6)−0.0020 (5)
C260.0192 (8)0.0205 (7)0.0235 (7)−0.0021 (6)0.0019 (6)−0.0026 (6)
C270.0187 (8)0.0239 (7)0.0192 (7)−0.0069 (6)−0.0007 (5)−0.0008 (6)
O280.0269 (6)0.0229 (5)0.0293 (6)−0.0059 (4)−0.0015 (4)−0.0096 (4)
C290.0319 (9)0.0225 (8)0.0340 (9)−0.0083 (7)−0.0084 (7)−0.0067 (7)
O300.0241 (6)0.0189 (5)0.0191 (5)−0.0053 (4)0.0002 (4)0.0013 (4)
C1—N21.4641 (18)C15—C201.394 (2)
C1—C61.5129 (19)C15—C161.398 (2)
C1—C81.5460 (18)C16—C171.386 (2)
C1—H11.0000C16—H160.9500
N2—C31.3485 (18)C17—C181.390 (2)
N2—C211.4633 (17)C17—H170.9500
C3—O301.2252 (17)C18—C191.383 (2)
C3—C41.5489 (19)C18—H180.9500
C4—N51.4922 (17)C19—C201.392 (2)
C4—C91.5149 (19)C19—H190.9500
C4—C71.5641 (18)C20—H200.9500
N5—C61.2820 (18)C21—C221.5070 (19)
C6—C151.4843 (19)C21—H21B0.9900
C7—C81.5322 (19)C21—H21A0.9900
C7—H7B0.9900C22—C231.393 (2)
C7—H7A0.9900C22—C271.394 (2)
C8—H8A0.9900C23—C241.393 (2)
C8—H8B0.9900C23—H230.9500
C9—C101.387 (2)C24—C251.395 (2)
C9—C141.391 (2)C24—H240.9500
C10—C111.391 (2)C25—O281.3653 (17)
C10—H100.9500C25—C261.393 (2)
C11—C121.382 (2)C26—C271.385 (2)
C11—H110.9500C26—H260.9500
C12—C131.384 (2)C27—H270.9500
C12—H120.9500O28—C291.4250 (18)
C13—C141.387 (2)C29—H29B0.9800
C13—H130.9500C29—H29C0.9800
C14—H140.9500C29—H29A0.9800
N2—C1—C6106.68 (11)C9—C14—H14119.3
N2—C1—C8107.79 (11)C20—C15—C16118.74 (13)
C6—C1—C8106.12 (11)C20—C15—C6121.48 (13)
N2—C1—H1112.0C16—C15—C6119.75 (12)
C6—C1—H1112.0C17—C16—C15120.75 (14)
C8—C1—H1112.0C17—C16—H16119.6
C3—N2—C21123.95 (12)C15—C16—H16119.6
C3—N2—C1115.85 (11)C16—C17—C18119.89 (15)
C21—N2—C1119.96 (11)C16—C17—H17120.1
O30—C3—N2125.58 (12)C18—C17—H17120.1
O30—C3—C4124.51 (12)C19—C18—C17119.93 (14)
N2—C3—C4109.89 (11)C19—C18—H18120.0
N5—C4—C9110.11 (11)C17—C18—H18120.0
N5—C4—C3108.07 (10)C18—C19—C20120.23 (14)
C9—C4—C3111.77 (11)C18—C19—H19119.9
N5—C4—C7107.65 (10)C20—C19—H19119.9
C9—C4—C7113.68 (11)C19—C20—C15120.42 (15)
C3—C4—C7105.25 (11)C19—C20—H20119.8
C6—N5—C4112.30 (11)C15—C20—H20119.8
N5—C6—C15121.31 (12)N2—C21—C22112.07 (11)
N5—C6—C1116.26 (12)N2—C21—H21B109.2
C15—C6—C1122.43 (12)C22—C21—H21B109.2
C8—C7—C4109.57 (11)N2—C21—H21A109.2
C8—C7—H7B109.8C22—C21—H21A109.2
C4—C7—H7B109.8H21B—C21—H21A107.9
C8—C7—H7A109.8C23—C22—C27118.15 (13)
C4—C7—H7A109.8C23—C22—C21121.17 (12)
H7B—C7—H7A108.2C27—C22—C21120.68 (12)
C7—C8—C1107.33 (11)C24—C23—C22121.73 (13)
C7—C8—H8A110.2C24—C23—H23119.1
C1—C8—H8A110.2C22—C23—H23119.1
C7—C8—H8B110.2C23—C24—C25119.11 (13)
C1—C8—H8B110.2C23—C24—H24120.4
H8A—C8—H8B108.5C25—C24—H24120.4
C10—C9—C14117.80 (13)O28—C25—C26115.66 (13)
C10—C9—C4122.53 (13)O28—C25—C24124.54 (13)
C14—C9—C4119.66 (12)C26—C25—C24119.80 (13)
C9—C10—C11121.05 (14)C27—C26—C25120.19 (13)
C9—C10—H10119.5C27—C26—H26119.9
C11—C10—H10119.5C25—C26—H26119.9
C12—C11—C10120.35 (14)C26—C27—C22121.01 (13)
C12—C11—H11119.8C26—C27—H27119.5
C10—C11—H11119.8C22—C27—H27119.5
C11—C12—C13119.34 (14)C25—O28—C29117.06 (11)
C11—C12—H12120.3O28—C29—H29B109.5
C13—C12—H12120.3O28—C29—H29C109.5
C12—C13—C14119.95 (14)H29B—C29—H29C109.5
C12—C13—H13120.0O28—C29—H29A109.5
C14—C13—H13120.0H29B—C29—H29A109.5
C13—C14—C9121.49 (13)H29C—C29—H29A109.5
C13—C14—H14119.3
C6—C1—N2—C351.84 (15)C4—C9—C10—C11−178.69 (13)
C8—C1—N2—C3−61.78 (15)C9—C10—C11—C12−1.2 (2)
C6—C1—N2—C21−133.60 (12)C10—C11—C12—C130.0 (2)
C8—C1—N2—C21112.78 (13)C11—C12—C13—C140.7 (2)
C21—N2—C3—O304.4 (2)C12—C13—C14—C9−0.1 (2)
C1—N2—C3—O30178.72 (12)C10—C9—C14—C13−1.1 (2)
C21—N2—C3—C4−174.13 (11)C4—C9—C14—C13179.33 (13)
C1—N2—C3—C40.19 (16)N5—C6—C15—C20153.12 (13)
O30—C3—C4—N5126.98 (13)C1—C6—C15—C20−28.10 (19)
N2—C3—C4—N5−54.46 (14)N5—C6—C15—C16−25.04 (19)
O30—C3—C4—C95.66 (18)C1—C6—C15—C16153.74 (13)
N2—C3—C4—C9−175.79 (11)C20—C15—C16—C170.8 (2)
O30—C3—C4—C7−118.21 (14)C6—C15—C16—C17178.97 (13)
N2—C3—C4—C760.35 (13)C15—C16—C17—C18−0.4 (2)
C9—C4—N5—C6176.59 (11)C16—C17—C18—C19−0.9 (2)
C3—C4—N5—C654.24 (14)C17—C18—C19—C201.9 (2)
C7—C4—N5—C6−58.98 (14)C18—C19—C20—C15−1.5 (2)
C4—N5—C6—C15178.84 (11)C16—C15—C20—C190.2 (2)
C4—N5—C6—C1−0.01 (16)C6—C15—C20—C19−177.95 (13)
N2—C1—C6—N5−53.75 (15)C3—N2—C21—C22−129.16 (13)
C8—C1—C6—N561.00 (15)C1—N2—C21—C2256.75 (16)
N2—C1—C6—C15127.41 (13)N2—C21—C22—C2359.17 (17)
C8—C1—C6—C15−117.83 (13)N2—C21—C22—C27−121.48 (14)
N5—C4—C7—C855.29 (14)C27—C22—C23—C240.2 (2)
C9—C4—C7—C8177.54 (11)C21—C22—C23—C24179.53 (12)
C3—C4—C7—C8−59.81 (13)C22—C23—C24—C25−0.5 (2)
C4—C7—C8—C12.67 (14)C23—C24—C25—O28−179.64 (13)
N2—C1—C8—C756.69 (14)C23—C24—C25—C260.3 (2)
C6—C1—C8—C7−57.31 (13)O28—C25—C26—C27−179.72 (12)
N5—C4—C9—C10134.06 (13)C24—C25—C26—C270.3 (2)
C3—C4—C9—C10−105.81 (15)C25—C26—C27—C22−0.7 (2)
C7—C4—C9—C1013.18 (18)C23—C22—C27—C260.5 (2)
N5—C4—C9—C14−46.41 (16)C21—C22—C27—C26−178.88 (13)
C3—C4—C9—C1473.72 (15)C26—C25—O28—C29170.61 (13)
C7—C4—C9—C14−167.29 (12)C24—C25—O28—C29−9.5 (2)
C14—C9—C10—C111.8 (2)
Cg1 and Cg2 are the centroids of the C22–C27 and C9–C14 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C19—H19···O28i0.952.513.457 (2)172
C13—H13···O30ii0.952.563.368 (2)143
C29—H29A···O30iii0.982.503.383 (2)150
C8—H8A···Cg2iv0.992.963.906 (2)159
C21—H21A···Cg1v0.992.563.411 (2)144
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C22–C27 and C9–C14 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8A⋯Cg2i0.992.963.906 (2)159
C21—H21A⋯Cg1ii0.992.563.411 (2)144
C19—H19⋯O28iii0.952.513.457 (2)172
C13—H13⋯O30iv0.952.563.368 (2)143
C29—H29A⋯O30v0.982.503.383 (2)150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  2 in total

1.  Synthesis of 2(1H)-pyrazinone phosphonates via an Arbuzov-type reaction.

Authors:  Jo Alen; Liliana Dobrzańska; Wim M De Borggraeve; Frans Compernolle
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total

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