Literature DB >> 25249888

1-[3-(Morpholin-4-yl)prop-yl]-3-[(naph-tha-len-2-yl)oxy]-4-(3-nitro-phen-yl)azeti-din-2-one.

Zeliha Atioğlu1, Mehmet Akkurt2, Aliasghar Jarrahpour3, Roghayeh Heiran3, Namık Ozdemir4.   

Abstract

In the title compound, C26H27N3O5, the β-lactam (azetidin-2-one) ring is nearly planar [maximum deviation = 0.011 (3) Å]. The mean plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation, the benzene ring and the naphthalene ring system form dihedral angles of 72.85 (17), 87.46 (15) and 65.96 (11)°, respectively, with the β-lactam ring. In the crystal, molecules are linked via C-H⋯O hydrogen bonds, forming inversion dimers with R 2 (2)(8).

Entities:  

Keywords:  crystal structure

Year:  2014        PMID: 25249888      PMCID: PMC4158481          DOI: 10.1107/S1600536814014949

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


Related literature

For general background to β-lactams, see: Mehta et al. (2010 ▶); Arumugam et al. (2011 ▶); Myangar & Raval (2012 ▶); Singh & Sudheesh (2014 ▶); Abdellaoui & Xu (2014 ▶); Cheng & Cheng (2007 ▶); Xiang (2013 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H27N3O5 M = 461.51 Triclinic, a = 9.7068 (8) Å b = 10.3836 (9) Å c = 14.2041 (11) Å α = 73.739 (6)° β = 75.922 (6)° γ = 63.107 (6)° V = 1214.33 (19) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 296 K 0.51 × 0.39 × 0.25 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.967, T max = 0.985 10059 measured reflections 4486 independent reflections 2123 reflections with I > 2σ(I) R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.066 wR(F 2) = 0.176 S = 0.95 4486 reflections 307 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.17 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014949/hg5396sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014949/hg5396Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814014949/hg5396Isup3.cml CCDC reference: 1010107 Additional supporting information: crystallographic information; 3D view; checkCIF report
C26H27N3O5Z = 2
Mr = 461.51F(000) = 488
Triclinic, P1Dx = 1.262 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7068 (8) ÅCell parameters from 9755 reflections
b = 10.3836 (9) Åθ = 1.5–28.8°
c = 14.2041 (11) ŵ = 0.09 mm1
α = 73.739 (6)°T = 296 K
β = 75.922 (6)°Block, light yellow
γ = 63.107 (6)°0.51 × 0.39 × 0.25 mm
V = 1214.33 (19) Å3
Stoe IPDS 2 diffractometer4486 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2123 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.088
Detector resolution: 6.67 pixels mm-1θmax = 25.5°, θmin = 2.2°
ω scansh = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −12→12
Tmin = 0.967, Tmax = 0.985l = −17→16
10059 measured reflections
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.176w = 1/[σ2(Fo2) + (0.0805P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
4486 reflectionsΔρmax = 0.28 e Å3
307 parametersΔρmin = −0.17 e Å3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those 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.
xyzUiso*/Ueq
O10.9297 (3)1.1424 (3)0.07366 (17)0.0961 (10)
O20.7976 (2)0.9168 (2)0.21877 (14)0.0753 (8)
O30.8014 (5)1.0509 (4)0.4976 (2)0.1465 (14)
O40.8408 (5)0.8838 (4)0.6243 (2)0.172 (2)
O51.7676 (3)0.5318 (3)−0.1356 (2)0.1070 (11)
N11.1173 (3)0.9410 (3)0.16271 (17)0.0677 (10)
N20.8603 (5)0.9237 (5)0.5366 (2)0.1089 (15)
N31.5567 (3)0.7649 (3)−0.03474 (17)0.0658 (9)
C10.9845 (4)1.0180 (4)0.1211 (2)0.0716 (11)
C20.9402 (4)0.8877 (4)0.1546 (2)0.0711 (11)
C31.0932 (4)0.8057 (3)0.2041 (2)0.0657 (11)
C40.7483 (4)0.8039 (4)0.2538 (2)0.0679 (11)
C50.6102 (4)0.8383 (4)0.3220 (2)0.0810 (11)
C60.5486 (4)0.7382 (5)0.3597 (2)0.0852 (14)
C70.6183 (4)0.5988 (4)0.3316 (2)0.0779 (13)
C80.5543 (5)0.4935 (6)0.3687 (3)0.0995 (18)
C90.6232 (6)0.3623 (6)0.3379 (4)0.114 (2)
C100.7574 (6)0.3308 (5)0.2710 (3)0.1057 (19)
C110.8243 (5)0.4271 (4)0.2350 (3)0.0871 (16)
C120.7571 (4)0.5656 (4)0.2643 (2)0.0723 (11)
C130.8214 (4)0.6705 (4)0.2268 (2)0.0715 (11)
C141.0772 (3)0.7610 (3)0.3149 (2)0.0618 (10)
C150.9834 (4)0.8625 (3)0.3742 (2)0.0703 (11)
C160.9656 (4)0.8152 (4)0.4753 (2)0.0739 (11)
C171.0402 (5)0.6725 (4)0.5206 (3)0.0847 (15)
C181.1351 (4)0.5718 (4)0.4615 (3)0.0848 (14)
C191.1519 (4)0.6162 (4)0.3600 (2)0.0763 (12)
C201.2491 (4)0.9733 (4)0.1582 (2)0.0791 (14)
C211.4021 (4)0.8613 (4)0.1168 (2)0.0746 (11)
C221.4024 (4)0.8513 (4)0.0131 (2)0.0718 (11)
C231.6225 (4)0.6141 (4)0.0167 (3)0.0847 (14)
C241.7765 (5)0.5274 (4)−0.0364 (3)0.1093 (17)
C251.7052 (5)0.6771 (4)−0.1862 (3)0.1020 (16)
C261.5468 (4)0.7661 (4)−0.1358 (2)0.0847 (13)
H20.945100.845800.099400.0850*
H31.170700.724200.172200.0790*
H50.562000.929300.340800.0970*
H60.458200.761000.405200.1030*
H80.464200.513800.414500.1190*
H90.579500.294100.362100.1370*
H100.803000.241300.250300.1270*
H110.915500.402500.190300.1040*
H130.914100.648300.183400.0860*
H150.932900.961500.346300.0850*
H171.027200.644100.589100.1010*
H181.188000.473600.490100.1020*
H191.215300.546600.321000.0910*
H20A1.256900.976400.224300.0950*
H20B1.231301.070000.117200.0950*
H21A1.485900.887800.117100.0890*
H21B1.422400.765300.159400.0890*
H22A1.332200.807300.014900.0860*
H22B1.362700.95000−0.026500.0860*
H23A1.551200.569300.022800.1020*
H23B1.635400.611600.082900.1020*
H24A1.850500.56620−0.036300.1310*
H24B1.814800.42580−0.001200.1310*
H25A1.696300.67850−0.253000.1220*
H25B1.775500.72220−0.190500.1220*
H26A1.507900.86680−0.172500.1010*
H26B1.474300.72500−0.134800.1010*
U11U22U33U12U13U23
O10.112 (2)0.0782 (16)0.0649 (14)−0.0169 (14)−0.0123 (13)−0.0032 (12)
O20.0629 (14)0.0846 (15)0.0576 (12)−0.0106 (12)−0.0013 (10)−0.0233 (11)
O30.178 (3)0.114 (2)0.082 (2)−0.006 (2)0.015 (2)−0.0443 (18)
O40.246 (5)0.162 (3)0.0539 (17)−0.057 (3)0.026 (2)−0.0303 (17)
O50.124 (2)0.0752 (17)0.0928 (19)−0.0129 (15)0.0003 (16)−0.0356 (14)
N10.0710 (19)0.0701 (16)0.0528 (14)−0.0232 (15)0.0043 (13)−0.0197 (12)
N20.136 (3)0.110 (3)0.0547 (19)−0.033 (2)0.0065 (18)−0.0251 (17)
N30.0670 (17)0.0656 (16)0.0528 (13)−0.0176 (12)−0.0016 (12)−0.0164 (11)
C10.084 (2)0.074 (2)0.0428 (15)−0.0215 (19)−0.0004 (16)−0.0171 (15)
C20.071 (2)0.086 (2)0.0449 (15)−0.0215 (17)0.0014 (15)−0.0230 (15)
C30.065 (2)0.0658 (19)0.0536 (16)−0.0155 (15)0.0038 (14)−0.0231 (14)
C40.058 (2)0.084 (2)0.0472 (15)−0.0167 (18)−0.0084 (14)−0.0122 (15)
C50.062 (2)0.092 (2)0.0609 (19)−0.0081 (19)0.0021 (16)−0.0233 (17)
C60.059 (2)0.115 (3)0.0569 (19)−0.020 (2)0.0055 (16)−0.0194 (19)
C70.060 (2)0.105 (3)0.0532 (18)−0.022 (2)−0.0069 (16)−0.0142 (18)
C80.080 (3)0.129 (4)0.080 (2)−0.040 (3)−0.005 (2)−0.017 (3)
C90.123 (4)0.126 (4)0.099 (3)−0.059 (3)−0.021 (3)−0.012 (3)
C100.118 (4)0.099 (3)0.093 (3)−0.039 (3)−0.017 (3)−0.016 (2)
C110.085 (3)0.090 (3)0.068 (2)−0.019 (2)−0.0080 (18)−0.0204 (19)
C120.060 (2)0.091 (2)0.0507 (16)−0.0171 (18)−0.0105 (15)−0.0134 (16)
C130.0550 (19)0.087 (2)0.0537 (17)−0.0114 (18)−0.0009 (14)−0.0228 (16)
C140.0565 (18)0.0656 (19)0.0569 (16)−0.0184 (15)−0.0073 (14)−0.0149 (14)
C150.082 (2)0.0648 (19)0.0496 (16)−0.0171 (16)−0.0044 (15)−0.0167 (13)
C160.088 (2)0.081 (2)0.0501 (17)−0.0328 (19)−0.0065 (16)−0.0150 (16)
C170.100 (3)0.096 (3)0.0556 (18)−0.043 (2)−0.0189 (19)0.0003 (19)
C180.090 (3)0.072 (2)0.082 (2)−0.029 (2)−0.029 (2)0.0073 (19)
C190.073 (2)0.069 (2)0.075 (2)−0.0176 (17)−0.0127 (17)−0.0144 (16)
C200.092 (3)0.086 (2)0.0628 (19)−0.036 (2)0.0025 (17)−0.0324 (16)
C210.074 (2)0.097 (2)0.0592 (18)−0.0372 (19)−0.0003 (16)−0.0291 (16)
C220.065 (2)0.086 (2)0.0564 (17)−0.0224 (17)−0.0041 (15)−0.0211 (15)
C230.094 (3)0.076 (2)0.070 (2)−0.022 (2)−0.0124 (19)−0.0149 (17)
C240.108 (3)0.080 (3)0.103 (3)−0.003 (2)−0.017 (2)−0.023 (2)
C250.123 (3)0.085 (3)0.071 (2)−0.024 (2)0.013 (2)−0.0307 (19)
C260.095 (3)0.082 (2)0.0551 (18)−0.0142 (19)−0.0082 (17)−0.0212 (15)
O1—C11.213 (4)C18—C191.378 (5)
O2—C21.414 (4)C20—C211.516 (5)
O2—C41.384 (4)C21—C221.505 (4)
O3—N21.200 (6)C23—C241.493 (6)
O4—N21.194 (4)C25—C261.510 (6)
O5—C241.419 (5)C2—H20.9800
O5—C251.392 (5)C3—H30.9800
N1—C11.351 (5)C5—H50.9300
N1—C31.464 (4)C6—H60.9300
N1—C201.446 (5)C8—H80.9300
N2—C161.465 (5)C9—H90.9300
N3—C221.463 (5)C10—H100.9300
N3—C231.441 (5)C11—H110.9300
N3—C261.458 (4)C13—H130.9300
C1—C21.519 (6)C15—H150.9300
C2—C31.566 (6)C17—H170.9300
C3—C141.501 (4)C18—H180.9300
C4—C51.411 (5)C19—H190.9300
C4—C131.358 (5)C20—H20A0.9700
C5—C61.349 (6)C20—H20B0.9700
C6—C71.421 (6)C21—H21A0.9700
C7—C81.411 (7)C21—H21B0.9700
C7—C121.409 (5)C22—H22A0.9700
C8—C91.365 (8)C22—H22B0.9700
C9—C101.376 (8)C23—H23A0.9700
C10—C111.350 (7)C23—H23B0.9700
C11—C121.422 (5)C24—H24A0.9700
C12—C131.410 (6)C24—H24B0.9700
C14—C151.380 (4)C25—H25A0.9700
C14—C191.377 (5)C25—H25B0.9700
C15—C161.376 (4)C26—H26A0.9700
C16—C171.362 (5)C26—H26B0.9700
C17—C181.375 (6)
C2—O2—C4117.4 (3)C14—C3—H3112.00
C24—O5—C25110.2 (3)C4—C5—H5120.00
C1—N1—C396.4 (3)C6—C5—H5120.00
C1—N1—C20132.1 (3)C5—C6—H6119.00
C3—N1—C20131.1 (3)C7—C6—H6119.00
O3—N2—O4121.9 (4)C7—C8—H8120.00
O3—N2—C16119.0 (3)C9—C8—H8120.00
O4—N2—C16119.0 (4)C8—C9—H9120.00
C22—N3—C23112.9 (3)C10—C9—H9120.00
C22—N3—C26109.7 (3)C9—C10—H10119.00
C23—N3—C26108.5 (3)C11—C10—H10119.00
O1—C1—N1131.9 (4)C10—C11—H11119.00
O1—C1—C2136.2 (4)C12—C11—H11120.00
N1—C1—C291.9 (3)C4—C13—H13120.00
O2—C2—C1113.2 (3)C12—C13—H13120.00
O2—C2—C3116.9 (2)C14—C15—H15121.00
C1—C2—C385.7 (3)C16—C15—H15120.00
N1—C3—C285.9 (2)C16—C17—H17121.00
N1—C3—C14115.7 (3)C18—C17—H17121.00
C2—C3—C14117.7 (3)C17—C18—H18120.00
O2—C4—C5114.0 (3)C19—C18—H18120.00
O2—C4—C13125.1 (3)C14—C19—H19119.00
C5—C4—C13120.9 (4)C18—C19—H19119.00
C4—C5—C6119.6 (4)N1—C20—H20A109.00
C5—C6—C7121.6 (4)N1—C20—H20B109.00
C6—C7—C8122.6 (4)C21—C20—H20A109.00
C6—C7—C12118.1 (4)C21—C20—H20B109.00
C8—C7—C12119.3 (4)H20A—C20—H20B108.00
C7—C8—C9120.6 (5)C20—C21—H21A109.00
C8—C9—C10120.1 (5)C20—C21—H21B109.00
C9—C10—C11121.4 (5)C22—C21—H21A109.00
C10—C11—C12120.9 (4)C22—C21—H21B109.00
C7—C12—C11117.7 (4)H21A—C21—H21B108.00
C7—C12—C13119.6 (3)N3—C22—H22A109.00
C11—C12—C13122.7 (4)N3—C22—H22B109.00
C4—C13—C12120.2 (3)C21—C22—H22A109.00
C3—C14—C15121.1 (3)C21—C22—H22B109.00
C3—C14—C19120.7 (3)H22A—C22—H22B108.00
C15—C14—C19118.2 (3)N3—C23—H23A109.00
C14—C15—C16119.1 (3)N3—C23—H23B109.00
N2—C16—C15118.2 (3)C24—C23—H23A109.00
N2—C16—C17118.8 (3)C24—C23—H23B109.00
C15—C16—C17123.1 (3)H23A—C23—H23B108.00
C16—C17—C18117.8 (4)O5—C24—H24A109.00
C17—C18—C19120.1 (4)O5—C24—H24B109.00
C14—C19—C18121.7 (3)C23—C24—H24A109.00
N1—C20—C21113.1 (3)C23—C24—H24B109.00
C20—C21—C22112.8 (3)H24A—C24—H24B108.00
N3—C22—C21113.6 (3)O5—C25—H25A109.00
N3—C23—C24111.5 (3)O5—C25—H25B109.00
O5—C24—C23112.4 (4)C26—C25—H25A109.00
O5—C25—C26112.0 (3)C26—C25—H25B109.00
N3—C26—C25110.4 (3)H25A—C25—H25B108.00
O2—C2—H2113.00N3—C26—H26A109.00
C1—C2—H2113.00N3—C26—H26B110.00
C3—C2—H2113.00C25—C26—H26A110.00
N1—C3—H3112.00C25—C26—H26B110.00
C2—C3—H3112.00H26A—C26—H26B108.00
C2—O2—C4—C5176.4 (3)C2—C3—C14—C15−54.0 (5)
C4—O2—C2—C1−179.5 (3)N1—C3—C14—C19−136.8 (4)
C4—O2—C2—C3−82.2 (4)O2—C4—C13—C12−177.4 (3)
C2—O2—C4—C13−4.1 (5)C5—C4—C13—C122.1 (5)
C25—O5—C24—C2355.7 (5)C13—C4—C5—C6−1.1 (5)
C24—O5—C25—C26−56.8 (5)O2—C4—C5—C6178.5 (3)
C20—N1—C1—C2171.6 (3)C4—C5—C6—C7−0.8 (5)
C3—N1—C1—O1179.9 (4)C5—C6—C7—C121.5 (5)
C20—N1—C1—O1−6.8 (6)C5—C6—C7—C8−178.8 (4)
C3—N1—C20—C2150.6 (4)C12—C7—C8—C9−1.8 (7)
C20—N1—C3—C1469.3 (4)C8—C7—C12—C13179.9 (4)
C1—N1—C3—C21.7 (2)C6—C7—C8—C9178.5 (4)
C1—N1—C20—C21−120.6 (4)C6—C7—C12—C11−178.7 (3)
C3—N1—C1—C2−1.7 (2)C6—C7—C12—C13−0.4 (5)
C1—N1—C3—C14−117.2 (3)C8—C7—C12—C111.5 (5)
C20—N1—C3—C2−171.8 (3)C7—C8—C9—C100.8 (8)
O3—N2—C16—C17175.7 (5)C8—C9—C10—C110.5 (8)
O4—N2—C16—C17−1.2 (8)C9—C10—C11—C12−0.7 (7)
O3—N2—C16—C15−4.8 (7)C10—C11—C12—C7−0.3 (6)
O4—N2—C16—C15178.3 (5)C10—C11—C12—C13−178.6 (4)
C26—N3—C22—C21−177.8 (3)C7—C12—C13—C4−1.4 (5)
C23—N3—C26—C25−56.2 (4)C11—C12—C13—C4176.9 (4)
C22—N3—C26—C25−179.9 (3)C3—C14—C19—C18−178.0 (4)
C22—N3—C23—C24177.4 (3)C19—C14—C15—C16−1.3 (6)
C26—N3—C23—C2455.6 (4)C3—C14—C15—C16176.5 (4)
C23—N3—C22—C2161.1 (4)C15—C14—C19—C18−0.1 (6)
O1—C1—C2—O2−62.7 (5)C14—C15—C16—C172.0 (7)
N1—C1—C2—O2119.1 (3)C14—C15—C16—N2−177.4 (4)
N1—C1—C2—C31.6 (2)N2—C16—C17—C18178.2 (4)
O1—C1—C2—C3179.8 (4)C15—C16—C17—C18−1.2 (7)
O2—C2—C3—C141.6 (4)C16—C17—C18—C19−0.3 (7)
C1—C2—C3—C14115.5 (3)C17—C18—C19—C140.9 (7)
O2—C2—C3—N1−115.4 (3)N1—C20—C21—C2260.0 (4)
C1—C2—C3—N1−1.5 (2)C20—C21—C22—N3169.3 (3)
C2—C3—C14—C19123.8 (4)N3—C23—C24—O5−56.3 (5)
N1—C3—C14—C1545.4 (5)O5—C25—C26—N358.4 (5)
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.982.463.229 (4)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
C2—H2⋯O1i 0.982.463.229 (4)135

Symmetry code: (i) .

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