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The title compound, C20H24N2O3, is a kind of non-cyclic crown ether. It crystallizes as a zigzag chain with two slightly asymmetric terminal groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006274/bt6033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006274/bt6033Isup2.hkl
Contains datablock I

CCDC reference: 170287

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.089
  • Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry





Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N,N'-Diethyl-N,N'-diphenyl-3-oxapentanediamide top
Crystal data top
C20H24N2O3F(000) = 728
Mr = 340.41Dx = 1.222 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.274 (2) ÅCell parameters from 25 reflections
b = 9.641 (1) Åθ = 3.1–13.0°
c = 20.746 (3) ŵ = 0.08 mm1
β = 94.17 (2)°T = 296 K
V = 1850.0 (5) Å3Block, yellow
Z = 40.68 × 0.38 × 0.22 mm
Data collection top
KappaCCD
diffractometer
2551 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω scansh = 1110
3250 measured reflectionsk = 011
3250 independent reflectionsl = 024
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters not refined
S = 1.01 w = 1/[σ2(Fo2) + (0.01P)2 + 0.51P]
where P = (Fo2 + 2Fc2)/3
3250 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.18736 (12)0.00035 (13)0.20178 (6)0.0635 (3)
O20.19608 (12)0.12435 (14)0.08371 (7)0.0751 (4)
O30.07956 (15)0.26279 (17)0.20930 (9)0.0983 (5)
N10.04239 (14)0.16217 (19)0.07189 (9)0.0791 (4)
N20.27265 (19)0.36191 (16)0.16739 (11)0.0919 (6)
C10.05449 (16)0.03711 (19)0.16792 (9)0.0590 (4)
H1C0.00030.09570.19520.080*
H1D0.00160.04620.15820.080*
C20.07740 (16)0.11331 (18)0.10532 (9)0.0587 (4)
C30.18633 (18)0.1602 (3)0.09539 (11)0.0791 (4)
C40.22960 (19)0.2629 (2)0.13459 (10)0.0748 (6)
H4A0.16340.32940.15030.080*
C50.3704 (2)0.2695 (2)0.15134 (11)0.0780 (6)
H5A0.39980.34090.17750.080*
C60.46692 (18)0.1696 (2)0.12900 (10)0.0696 (5)
H6A0.56220.17250.14020.080*
C70.4223 (2)0.0663 (2)0.09037 (11)0.0776 (6)
H7A0.48710.00230.07570.080*
C80.2833 (2)0.0627 (2)0.07301 (11)0.0770 (6)
H8A0.25470.00700.04570.080*
C90.0368 (3)0.1888 (3)0.00112 (19)0.1481 (10)
H9A0.04570.14570.01920.080*
H9B0.12560.16380.02600.080*
C100.0195 (3)0.3418 (3)0.00833 (19)0.1481 (10)
H10A0.06240.38950.02890.080*
H10B0.08140.36430.01400.080*
H10C0.06650.36970.04600.080*
C110.26283 (17)0.11108 (17)0.17525 (9)0.0577 (4)
H11A0.36180.11080.19400.080*
H11B0.26550.09640.12910.080*
C120.19756 (19)0.2505 (2)0.18634 (10)0.0703 (5)
C130.4126 (2)0.35088 (19)0.14132 (12)0.0726 (5)
C140.5366 (3)0.3489 (2)0.18199 (12)0.0825 (6)
H14A0.53080.35170.22650.080*
C150.6701 (3)0.3427 (2)0.15607 (14)0.0928 (7)
H15A0.75500.34460.18280.080*
C160.6747 (3)0.3337 (3)0.09061 (17)0.1083 (9)
H16A0.76340.32520.07270.080*
C170.5526 (3)0.3371 (3)0.05173 (14)0.1093 (9)
H17A0.55720.33350.00710.080*
C180.4216 (3)0.3459 (3)0.07747 (13)0.0974 (8)
H18A0.33760.34840.05020.080*
C190.2046 (3)0.5049 (3)0.16474 (15)0.1195 (10)
H19A0.10000.49760.16120.080*
H19B0.23450.55600.12770.080*
C200.2539 (3)0.5753 (4)0.22466 (15)0.1303 (11)
H20A0.24480.67370.21890.080*
H20B0.19600.54610.25870.080*
H20C0.35330.55220.23580.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0485 (6)0.0742 (8)0.0665 (7)0.0155 (6)0.0043 (5)0.0065 (6)
O20.0370 (6)0.0896 (10)0.1005 (10)0.0028 (6)0.0178 (6)0.0256 (8)
O30.0639 (9)0.0920 (11)0.1441 (14)0.0149 (8)0.0420 (9)0.0462 (10)
N10.0351 (6)0.1111 (11)0.0933 (9)0.0211 (6)0.0194 (6)0.0488 (8)
N20.0734 (11)0.0448 (9)0.1635 (19)0.0090 (8)0.0492 (12)0.0218 (10)
C10.0375 (8)0.0694 (11)0.0708 (11)0.0106 (8)0.0079 (7)0.0023 (9)
C20.0370 (8)0.0576 (10)0.0823 (12)0.0027 (7)0.0099 (8)0.0093 (9)
C30.0351 (6)0.1111 (11)0.0933 (9)0.0211 (6)0.0194 (6)0.0488 (8)
C40.0409 (9)0.0910 (15)0.0910 (14)0.0136 (9)0.0048 (9)0.0001 (12)
C50.0563 (11)0.0845 (14)0.0952 (15)0.0081 (10)0.0183 (10)0.0158 (12)
C60.0334 (8)0.0938 (15)0.0819 (13)0.0065 (9)0.0055 (8)0.0028 (11)
C70.0555 (11)0.0846 (14)0.0946 (15)0.0120 (10)0.0189 (10)0.0093 (12)
C80.0582 (11)0.0687 (12)0.1079 (16)0.0061 (10)0.0311 (11)0.0025 (11)
C90.0678 (11)0.151 (2)0.227 (3)0.0005 (13)0.0197 (14)0.065 (2)
C100.0678 (11)0.151 (2)0.227 (3)0.0005 (13)0.0197 (14)0.065 (2)
C110.0461 (9)0.0555 (10)0.0718 (11)0.0139 (7)0.0064 (8)0.0043 (8)
C120.0539 (10)0.0677 (12)0.0909 (14)0.0052 (9)0.0160 (10)0.0311 (11)
C130.0650 (12)0.0540 (11)0.1006 (16)0.0128 (9)0.0182 (11)0.0065 (11)
C140.0930 (16)0.0688 (13)0.0870 (15)0.0111 (12)0.0160 (13)0.0020 (11)
C150.0681 (14)0.0908 (17)0.120 (2)0.0118 (12)0.0092 (14)0.0038 (15)
C160.0960 (19)0.0882 (17)0.149 (3)0.0206 (15)0.0646 (19)0.0142 (17)
C170.133 (2)0.111 (2)0.0885 (18)0.0423 (19)0.0391 (18)0.0118 (15)
C180.0899 (17)0.1023 (19)0.0992 (19)0.0328 (14)0.0004 (14)0.0029 (15)
C190.107 (2)0.130 (3)0.117 (2)0.0054 (18)0.0213 (17)0.0097 (19)
C200.093 (2)0.160 (3)0.140 (3)0.009 (2)0.0258 (19)0.005 (2)
Geometric parameters (Å, º) top
O1—C111.4153 (19)C9—H9A0.9700
O1—C11.4183 (19)C9—H9B0.9700
O2—C21.2229 (19)C10—H10A0.9600
O3—C121.230 (2)C10—H10B0.9600
N1—C21.351 (2)C10—H10C0.9600
N1—C31.454 (2)C11—C121.499 (2)
N1—C91.541 (4)C11—H11A0.9700
N2—C121.354 (2)C11—H11B0.9700
N2—C131.446 (2)C13—C181.334 (3)
N2—C191.516 (3)C13—C141.376 (3)
C1—C21.521 (2)C14—C151.387 (3)
C1—H1C0.9700C14—H14A0.9300
C1—H1D0.9700C15—C161.365 (4)
C3—C81.359 (3)C15—H15A0.9300
C3—C41.360 (3)C16—C171.342 (4)
C4—C51.377 (2)C16—H16A0.9300
C4—H4A0.9300C17—C181.364 (3)
C5—C61.372 (3)C17—H17A0.9300
C5—H5A0.9300C18—H18A0.9300
C6—C71.362 (3)C19—C201.460 (4)
C6—H6A0.9300C19—H19A0.9700
C7—C81.364 (2)C19—H19B0.9700
C7—H7A0.9300C20—H20A0.9600
C8—H8A0.9300C20—H20B0.9600
C9—C101.495 (4)C20—H20C0.9600
C11—O1—C1115.69 (13)C9—C10—H10C109.5
C2—N1—C3124.33 (16)H10A—C10—H10C109.5
C2—N1—C9118.53 (17)H10B—C10—H10C109.5
C3—N1—C9115.41 (17)O1—C11—C12113.85 (14)
C12—N2—C13123.02 (16)O1—C11—H11A108.8
C12—N2—C19120.70 (18)C12—C11—H11A108.8
C13—N2—C19115.86 (18)O1—C11—H11B108.8
O1—C1—C2111.93 (13)C12—C11—H11B108.8
O1—C1—H1C109.2H11A—C11—H11B107.7
C2—C1—H1C109.2O3—C12—N2121.78 (18)
O1—C1—H1D109.2O3—C12—C11121.75 (18)
C2—C1—H1D109.2N2—C12—C11116.42 (15)
H1C—C1—H1D107.9C18—C13—C14119.9 (2)
O2—C2—N1120.66 (17)C18—C13—N2119.8 (2)
O2—C2—C1122.73 (15)C14—C13—N2120.3 (2)
N1—C2—C1116.50 (14)C13—C14—C15119.5 (2)
C8—C3—C4119.42 (16)C13—C14—H14A120.2
C8—C3—N1119.7 (2)C15—C14—H14A120.2
C4—C3—N1120.6 (2)C16—C15—C14118.8 (2)
C3—C4—C5120.72 (19)C16—C15—H15A120.6
C3—C4—H4A119.6C14—C15—H15A120.6
C5—C4—H4A119.6C17—C16—C15120.7 (2)
C6—C5—C4119.32 (19)C17—C16—H16A119.7
C6—C5—H5A120.3C15—C16—H16A119.7
C4—C5—H5A120.3C16—C17—C18120.2 (3)
C7—C6—C5119.56 (17)C16—C17—H17A119.9
C7—C6—H6A120.2C18—C17—H17A119.9
C5—C6—H6A120.2C13—C18—C17120.8 (3)
C6—C7—C8120.6 (2)C13—C18—H18A119.6
C6—C7—H7A119.7C17—C18—H18A119.6
C8—C7—H7A119.7C20—C19—N2106.7 (2)
C3—C8—C7120.4 (2)C20—C19—H19A110.4
C3—C8—H8A119.8N2—C19—H19A110.4
C7—C8—H8A119.8C20—C19—H19B110.4
C10—C9—N192.7 (3)N2—C19—H19B110.4
C10—C9—H9A113.2H19A—C19—H19B108.6
N1—C9—H9A113.2C19—C20—H20A109.5
C10—C9—H9B113.2C19—C20—H20B109.5
N1—C9—H9B113.2H20A—C20—H20B109.5
H9A—C9—H9B110.5C19—C20—H20C109.5
C9—C10—H10A109.5H20A—C20—H20C109.5
C9—C10—H10B109.5H20B—C20—H20C109.5
H10A—C10—H10B109.5
C11—O1—C1—C273.95 (19)C1—O1—C11—C1274.42 (19)
C3—N1—C2—O2176.5 (2)C13—N2—C12—O3178.9 (2)
C9—N1—C2—O219.2 (3)C19—N2—C12—O38.9 (4)
C3—N1—C2—C17.3 (3)C13—N2—C12—C113.6 (3)
C9—N1—C2—C1157.0 (2)C19—N2—C12—C11168.6 (2)
O1—C1—C2—O28.8 (3)O1—C11—C12—O38.5 (3)
O1—C1—C2—N1175.12 (17)O1—C11—C12—N2173.99 (18)
C2—N1—C3—C8102.4 (3)C12—N2—C13—C1894.7 (3)
C9—N1—C3—C862.3 (3)C19—N2—C13—C1877.9 (3)
C2—N1—C3—C484.1 (3)C12—N2—C13—C1486.9 (3)
C9—N1—C3—C4111.1 (3)C19—N2—C13—C14100.5 (3)
C8—C3—C4—C50.5 (3)C18—C13—C14—C150.4 (3)
N1—C3—C4—C5173.03 (18)N2—C13—C14—C15177.98 (19)
C3—C4—C5—C61.2 (3)C13—C14—C15—C162.3 (3)
C4—C5—C6—C70.4 (3)C14—C15—C16—C173.0 (4)
C5—C6—C7—C81.0 (3)C15—C16—C17—C181.8 (4)
C4—C3—C8—C70.9 (3)C14—C13—C18—C170.8 (4)
N1—C3—C8—C7174.50 (19)N2—C13—C18—C17179.2 (2)
C6—C7—C8—C31.7 (3)C16—C17—C18—C130.1 (4)
C2—N1—C9—C10101.7 (2)C12—N2—C19—C2097.7 (3)
C3—N1—C9—C1092.6 (2)C13—N2—C19—C2089.5 (3)
 

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