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The title compound, C20H26N2O3·0.5H2O, contains a 17-membered di­aza-crown ether ligand with three ether O and two N atoms. It consists of the macrocyclic ligand and one half water mol­ecule; the latter possesses crystallographically imposed C2 symmetry. In the macrocyclic ring, the mean N...O distance is 3.995 (4) Å. The macrocyclic inner hole size, estimated as twice the mean distance of the donor atoms from their centroid, is approximately 1.29 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021615/cm6055sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021615/cm6055Isup2.hkl
Contains datablock I

CCDC reference: 226937

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.052
  • wR factor = 0.169
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O26 - H26 ... ?
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadle, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C20H26N2O3·0.5H2OF(000) = 1512
Mr = 351.44Dx = 1.192 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 24.457 (2) Åθ = 10–18°
b = 7.5165 (12) ŵ = 0.08 mm1
c = 23.865 (2) ÅT = 293 K
β = 116.768 (9)°Rod shaped, colourless
V = 3917.0 (8) Å30.40 × 0.25 × 0.15 mm
Z = 8
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.022
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.9°
Graphite monochromatorh = 030
non–profiled ω scansk = 09
3856 measured reflectionsl = 2729
3786 independent reflections3 standard reflections every 120 min
1752 reflections with I > 2σ(I) intensity decay: 1%
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)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0951P)2 + 0.1096P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3163 reflectionsΔρmax = 0.51 e Å3
242 parametersΔρmin = 0.24 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (5)
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
O260.00000.8760 (6)0.25000.130
H80.1216 (14)0.075 (4)0.3627 (13)0.071 (9)*
H260.0316 (12)0.916 (4)0.2405 (12)0.075*
H110.1465 (13)0.321 (3)0.3299 (14)0.075*
H20.2605 (15)0.027 (4)0.5687 (13)0.072 (9)*
O190.17834 (8)0.2592 (2)0.24813 (8)0.0699 (5)
O220.22177 (9)0.0241 (2)0.35207 (9)0.0690 (6)
O250.20186 (8)0.0789 (2)0.45371 (9)0.0676 (5)
N110.13632 (13)0.4231 (4)0.33408 (12)0.0792 (8)
N80.08400 (13)0.0684 (4)0.35653 (11)0.0755 (8)
C60.11695 (14)0.0064 (4)0.46899 (13)0.0679 (8)
C10.18040 (14)0.0154 (3)0.49357 (12)0.0599 (7)
C130.11233 (13)0.5043 (4)0.22189 (13)0.0635 (7)
C20.21807 (18)0.0393 (4)0.55449 (14)0.0701 (8)
C180.13043 (12)0.3531 (4)0.20192 (13)0.0624 (7)
C230.26748 (15)0.0654 (4)0.40503 (16)0.0800 (9)
H23A0.30780.02980.41070.096*
H23B0.26360.19280.39800.096*
C170.10319 (15)0.3043 (5)0.13910 (14)0.0806 (9)
H170.11570.20200.12620.097*
C30.1928 (2)0.1020 (4)0.59099 (15)0.0855 (10)
H30.21820.13850.63180.103*
C120.14166 (15)0.5542 (4)0.29084 (14)0.0731 (8)
H12A0.18480.57640.30420.088*
H12B0.12360.66500.29510.088*
C240.26073 (14)0.0211 (4)0.46244 (14)0.0720 (8)
H24A0.29250.08000.49860.086*
H24B0.26480.10630.46970.086*
C200.17801 (17)0.0706 (4)0.24199 (15)0.0825 (9)
H20A0.18180.03860.20450.099*
H20B0.13980.02220.23850.099*
C210.23002 (17)0.0026 (4)0.29805 (16)0.0828 (10)
H21A0.23380.12890.29220.099*
H21B0.26760.05490.30350.099*
C40.1304 (2)0.1123 (4)0.56853 (18)0.0923 (11)
H40.11350.15500.59390.111*
C140.06591 (15)0.6064 (4)0.17652 (15)0.0784 (9)
H140.05300.70940.18860.094*
C150.03892 (17)0.5581 (5)0.11436 (16)0.0892 (10)
H150.00800.62800.08480.107*
C70.07780 (15)0.0545 (5)0.40125 (14)0.0838 (10)
H7A0.08860.17340.39390.101*
H7B0.03530.05690.39330.101*
C90.06774 (14)0.2495 (5)0.36249 (13)0.0789 (9)
H9A0.09360.29050.40490.095*
H9B0.02570.25210.35610.095*
C100.07427 (15)0.3773 (5)0.31624 (14)0.0877 (10)
H10A0.05690.32270.27500.105*
H10B0.05120.48470.31340.105*
C50.09277 (17)0.0578 (5)0.50723 (16)0.0892 (10)
H50.05050.06490.49180.107*
C160.05732 (17)0.4094 (6)0.09617 (15)0.0928 (11)
H160.03880.37730.05400.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O260.1600.1060.1080.0000.0450.000
O190.0786 (12)0.0583 (12)0.0750 (12)0.0008 (10)0.0367 (10)0.0041 (10)
O220.0841 (13)0.0540 (11)0.0787 (13)0.0185 (10)0.0453 (11)0.0129 (9)
O250.0740 (12)0.0548 (11)0.0687 (11)0.0085 (9)0.0275 (10)0.0004 (9)
N110.0848 (19)0.0798 (19)0.0669 (14)0.0089 (15)0.0289 (13)0.0060 (15)
N80.0636 (17)0.098 (2)0.0574 (14)0.0029 (15)0.0209 (13)0.0058 (13)
C60.076 (2)0.0645 (19)0.0623 (17)0.0058 (14)0.0298 (16)0.0166 (14)
C10.079 (2)0.0407 (15)0.0523 (15)0.0069 (13)0.0231 (15)0.0073 (12)
C130.0657 (17)0.0566 (18)0.0700 (18)0.0097 (14)0.0322 (15)0.0017 (15)
C20.088 (2)0.0511 (17)0.0590 (19)0.0050 (16)0.0217 (18)0.0131 (14)
C180.0663 (17)0.0618 (18)0.0652 (17)0.0063 (14)0.0350 (15)0.0024 (14)
C230.087 (2)0.0565 (18)0.104 (2)0.0207 (16)0.0496 (19)0.0217 (17)
C170.096 (2)0.086 (2)0.0712 (19)0.0100 (19)0.0477 (18)0.0094 (18)
C30.134 (3)0.0565 (19)0.0612 (19)0.0072 (19)0.040 (2)0.0084 (14)
C120.0817 (19)0.0604 (18)0.0755 (19)0.0158 (15)0.0340 (16)0.0066 (15)
C240.073 (2)0.0533 (17)0.0777 (19)0.0032 (14)0.0238 (16)0.0147 (15)
C200.116 (3)0.059 (2)0.083 (2)0.0009 (18)0.054 (2)0.0085 (16)
C210.115 (3)0.0593 (19)0.099 (2)0.0166 (18)0.071 (2)0.0047 (17)
C40.140 (4)0.075 (2)0.083 (3)0.016 (2)0.068 (3)0.0194 (18)
C140.088 (2)0.070 (2)0.079 (2)0.0028 (17)0.0394 (18)0.0085 (17)
C150.090 (2)0.094 (3)0.075 (2)0.001 (2)0.0309 (19)0.019 (2)
C70.076 (2)0.091 (2)0.071 (2)0.0205 (17)0.0210 (17)0.0056 (17)
C90.0732 (18)0.100 (3)0.0660 (17)0.0006 (18)0.0338 (15)0.0096 (17)
C100.077 (2)0.119 (3)0.0607 (17)0.005 (2)0.0257 (16)0.0112 (18)
C50.091 (2)0.099 (3)0.084 (2)0.0061 (19)0.045 (2)0.032 (2)
C160.099 (3)0.115 (3)0.0592 (18)0.013 (2)0.0314 (19)0.006 (2)
Geometric parameters (Å, º) top
O26—H260.95 (3)C17—H170.9300
O19—C181.387 (3)C3—C41.374 (5)
O19—C201.425 (3)C3—H30.9300
O22—C211.406 (3)C12—H12A0.9700
O22—C231.424 (4)C12—H12B0.9700
O25—C11.363 (3)C24—H24A0.9700
O25—C241.427 (4)C24—H24B0.9700
N11—C101.422 (4)C20—C211.475 (5)
N11—C121.475 (4)C20—H20A0.9700
N11—H110.829 (17)C20—H20B0.9700
N8—C91.443 (4)C21—H21A0.9700
N8—C71.470 (4)C21—H21B0.9700
N8—H80.86 (3)C4—C51.393 (5)
C6—C51.379 (4)C4—H40.9300
C6—C11.392 (4)C14—C151.373 (5)
C6—C71.506 (4)C14—H140.9300
C1—C21.387 (4)C15—C161.348 (5)
C13—C181.380 (4)C15—H150.9300
C13—C141.394 (4)C7—H7A0.9700
C13—C121.516 (4)C7—H7B0.9700
C2—C31.359 (5)C9—C101.525 (4)
C2—H20.94 (3)C9—H9A0.9700
C18—C171.388 (4)C9—H9B0.9700
C23—C241.490 (4)C10—H10A0.9700
C23—H23A0.9700C10—H10B0.9700
C23—H23B0.9700C5—H50.9300
C17—C161.377 (5)C16—H160.9300
C18—O19—C20117.5 (2)H24A—C24—H24B108.3
C21—O22—C23111.6 (2)O19—C20—C21108.4 (3)
C1—O25—C24118.2 (2)O19—C20—H20A110.0
C10—N11—C12111.8 (2)C21—C20—H20A110.0
C10—N11—H1194 (2)O19—C20—H20B110.0
C12—N11—H11114 (2)C21—C20—H20B110.0
C9—N8—C7113.5 (3)H20A—C20—H20B108.4
C9—N8—H8104 (2)O22—C21—C20110.9 (2)
C7—N8—H8111.3 (19)O22—C21—H21A109.5
C5—C6—C1117.8 (3)C20—C21—H21A109.5
C5—C6—C7122.7 (3)O22—C21—H21B109.5
C1—C6—C7119.3 (3)C20—C21—H21B109.5
O25—C1—C2123.5 (3)H21A—C21—H21B108.0
O25—C1—C6115.4 (2)C3—C4—C5119.1 (3)
C2—C1—C6121.0 (3)C3—C4—H4120.5
C18—C13—C14117.4 (3)C5—C4—H4120.5
C18—C13—C12120.7 (3)C15—C14—C13121.4 (3)
C14—C13—C12121.9 (3)C15—C14—H14119.3
C3—C2—C1119.7 (4)C13—C14—H14119.3
C3—C2—H2123.2 (17)C16—C15—C14120.0 (3)
C1—C2—H2117.0 (17)C16—C15—H15120.0
C13—C18—O19115.6 (2)C14—C15—H15120.0
C13—C18—C17121.2 (3)N8—C7—C6113.9 (2)
O19—C18—C17123.1 (3)N8—C7—H7A108.8
O22—C23—C24110.1 (2)C6—C7—H7A108.8
O22—C23—H23A109.6N8—C7—H7B108.8
C24—C23—H23A109.6C6—C7—H7B108.8
O22—C23—H23B109.6H7A—C7—H7B107.7
C24—C23—H23B109.6N8—C9—C10113.5 (3)
H23A—C23—H23B108.2N8—C9—H9A108.9
C16—C17—C18119.0 (3)C10—C9—H9A108.9
C16—C17—H17120.5N8—C9—H9B108.9
C18—C17—H17120.5C10—C9—H9B108.9
C2—C3—C4121.0 (3)H9A—C9—H9B107.7
C2—C3—H3119.5N11—C10—C9112.4 (3)
C4—C3—H3119.5N11—C10—H10A109.1
N11—C12—C13116.5 (2)C9—C10—H10A109.1
N11—C12—H12A108.2N11—C10—H10B109.1
C13—C12—H12A108.2C9—C10—H10B109.1
N11—C12—H12B108.2H10A—C10—H10B107.8
C13—C12—H12B108.2C6—C5—C4121.3 (3)
H12A—C12—H12B107.3C6—C5—H5119.3
O25—C24—C23108.7 (2)C4—C5—H5119.3
O25—C24—H24A110.0C15—C16—C17121.0 (3)
C23—C24—H24A110.0C15—C16—H16119.5
O25—C24—H24B110.0C17—C16—H16119.5
C23—C24—H24B110.0
C24—O25—C1—C227.1 (3)C1—O25—C24—C23164.8 (2)
C24—O25—C1—C6152.2 (2)O22—C23—C24—O2560.9 (3)
C5—C6—C1—O25179.7 (2)C18—O19—C20—C21175.8 (2)
C7—C6—C1—O253.7 (4)C23—O22—C21—C20172.5 (3)
C5—C6—C1—C20.3 (4)O19—C20—C21—O2266.6 (3)
C7—C6—C1—C2175.6 (3)C2—C3—C4—C50.2 (5)
O25—C1—C2—C3179.6 (2)C18—C13—C14—C150.4 (4)
C6—C1—C2—C30.3 (4)C12—C13—C14—C15178.8 (3)
C14—C13—C18—O19177.5 (2)C13—C14—C15—C160.1 (5)
C12—C13—C18—O193.3 (4)C9—N8—C7—C659.7 (4)
C14—C13—C18—C170.4 (4)C5—C6—C7—N8109.5 (3)
C12—C13—C18—C17178.8 (2)C1—C6—C7—N866.2 (4)
C20—O19—C18—C13146.5 (3)C7—N8—C9—C10179.9 (2)
C20—O19—C18—C1735.6 (4)C12—N11—C10—C9176.9 (3)
C21—O22—C23—C24174.9 (2)N8—C9—C10—N1176.5 (4)
C13—C18—C17—C160.1 (4)C1—C6—C5—C40.1 (5)
O19—C18—C17—C16177.7 (3)C7—C6—C5—C4175.7 (3)
C1—C2—C3—C40.0 (4)C3—C4—C5—C60.2 (5)
C10—N11—C12—C1355.5 (4)C14—C15—C16—C170.2 (5)
C18—C13—C12—N1159.3 (4)C18—C17—C16—C150.2 (5)
C14—C13—C12—N11119.8 (3)
 

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