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The title compound, C18H20N2O3, has twofold rotation symmetry. Mol­ecules are linked into ribbons along the c axis by N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012797/is2023sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012797/is2023Isup2.hkl
Contains datablock I

CCDC reference: 608424

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.133
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N,N'-Bis(4-methylphenyl)-3-oxapentanediamide top
Crystal data top
C18H20N2O3F(000) = 664
Mr = 312.36Dx = 1.274 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 29.059 (3) ÅCell parameters from 1687 reflections
b = 6.2798 (7) Åθ = 2.8–25.6°
c = 8.9209 (10) ŵ = 0.09 mm1
β = 90.299 (2)°T = 293 K
V = 1627.9 (3) Å3Column, dark-brown
Z = 40.33 × 0.24 × 0.11 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1606 independent reflections
Radiation source: fine-focus sealed tube1278 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.8°
ω scansh = 3519
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 77
Tmin = 0.972, Tmax = 0.990l = 1110
4509 measured reflections
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) = 0.133H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0709P)2 + 0.5191P]
where P = (Fo2 + 2Fc2)/3
1606 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.15 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
O10.44624 (4)0.2291 (2)0.59977 (12)0.0670 (4)
O20.50000.1581 (2)0.25000.0638 (5)
N10.43010 (4)0.0061 (2)0.40447 (13)0.0531 (4)
H1A0.43870.02600.31520.064*
C10.28081 (7)0.5011 (4)0.6230 (2)0.0864 (6)
H1B0.28060.63510.57130.130*
H1C0.25240.42760.60370.130*
H1D0.28410.52550.72880.130*
C20.32059 (6)0.3675 (3)0.56842 (18)0.0614 (5)
C30.34980 (6)0.4399 (3)0.45754 (18)0.0622 (5)
H3A0.34510.57480.41720.075*
C40.38568 (6)0.3170 (3)0.40524 (18)0.0575 (4)
H4A0.40460.36920.33000.069*
C50.39360 (5)0.1162 (2)0.46449 (15)0.0487 (4)
C60.36468 (5)0.0405 (3)0.57568 (17)0.0564 (4)
H6A0.36920.09450.61600.068*
C70.32909 (6)0.1674 (3)0.62610 (19)0.0630 (5)
H7A0.31020.11600.70170.076*
C80.45277 (5)0.1669 (2)0.47189 (17)0.0499 (4)
C90.48804 (6)0.2789 (3)0.37662 (17)0.0552 (4)
H9A0.47580.41520.34440.066*
H9B0.51540.30580.43630.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0707 (8)0.0827 (9)0.0478 (7)0.0105 (6)0.0151 (6)0.0069 (6)
O20.0779 (11)0.0488 (8)0.0653 (10)0.0000.0383 (8)0.000
N10.0539 (8)0.0635 (8)0.0422 (6)0.0002 (6)0.0151 (5)0.0009 (6)
C10.0659 (12)0.1075 (16)0.0859 (13)0.0261 (11)0.0046 (10)0.0145 (12)
C20.0518 (9)0.0785 (11)0.0539 (9)0.0072 (8)0.0013 (7)0.0123 (8)
C30.0664 (11)0.0619 (10)0.0583 (9)0.0054 (8)0.0002 (8)0.0041 (8)
C40.0594 (10)0.0637 (10)0.0495 (9)0.0065 (8)0.0091 (7)0.0015 (7)
C50.0447 (8)0.0595 (9)0.0419 (7)0.0028 (7)0.0054 (6)0.0062 (6)
C60.0523 (9)0.0661 (10)0.0510 (8)0.0007 (8)0.0116 (7)0.0025 (8)
C70.0480 (9)0.0859 (12)0.0552 (9)0.0008 (8)0.0152 (7)0.0011 (8)
C80.0476 (8)0.0573 (9)0.0449 (8)0.0073 (7)0.0076 (6)0.0042 (7)
C90.0561 (9)0.0562 (9)0.0535 (9)0.0032 (7)0.0142 (7)0.0012 (7)
Geometric parameters (Å, º) top
O1—C81.2216 (18)C3—C41.380 (2)
O2—C9i1.4059 (16)C3—H3A0.9300
O2—C91.4059 (16)C4—C51.386 (2)
N1—C81.346 (2)C4—H4A0.9300
N1—C51.4166 (19)C5—C61.387 (2)
N1—H1A0.8600C6—C71.383 (2)
C1—C21.511 (2)C6—H6A0.9300
C1—H1B0.9600C7—H7A0.9300
C1—H1C0.9600C8—C91.509 (2)
C1—H1D0.9600C9—H9A0.9700
C2—C71.380 (3)C9—H9B0.9700
C2—C31.384 (2)
C9i—O2—C9114.67 (16)C4—C5—C6118.95 (15)
C8—N1—C5127.11 (12)C4—C5—N1118.17 (13)
C8—N1—H1A116.4C6—C5—N1122.84 (15)
C5—N1—H1A116.4C7—C6—C5119.49 (16)
C2—C1—H1B109.5C7—C6—H6A120.3
C2—C1—H1C109.5C5—C6—H6A120.3
H1B—C1—H1C109.5C2—C7—C6122.43 (15)
C2—C1—H1D109.5C2—C7—H7A118.8
H1B—C1—H1D109.5C6—C7—H7A118.8
H1C—C1—H1D109.5O1—C8—N1125.40 (14)
C7—C2—C3117.17 (16)O1—C8—C9119.08 (15)
C7—C2—C1121.40 (17)N1—C8—C9115.50 (13)
C3—C2—C1121.42 (18)O2—C9—C8111.85 (13)
C4—C3—C2121.69 (17)O2—C9—H9A109.2
C4—C3—H3A119.2C8—C9—H9A109.2
C2—C3—H3A119.2O2—C9—H9B109.2
C3—C4—C5120.26 (15)C8—C9—H9B109.2
C3—C4—H4A119.9H9A—C9—H9B107.9
C5—C4—H4A119.9
C7—C2—C3—C40.7 (3)C3—C2—C7—C60.9 (3)
C1—C2—C3—C4178.78 (16)C1—C2—C7—C6178.60 (17)
C2—C3—C4—C50.6 (3)C5—C6—C7—C20.9 (3)
C3—C4—C5—C60.6 (2)C5—N1—C8—O12.5 (3)
C3—C4—C5—N1178.39 (14)C5—N1—C8—C9175.85 (14)
C8—N1—C5—C4157.20 (15)C9i—O2—C9—C8148.65 (16)
C8—N1—C5—C625.1 (2)O1—C8—C9—O2164.67 (14)
C4—C5—C6—C70.8 (2)N1—C8—C9—O216.8 (2)
N1—C5—C6—C7178.44 (14)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1ii0.862.323.131 (2)158
C4—H4A···O1ii0.932.553.298 (2)138
C6—H6A···O10.932.402.920 (2)115
Symmetry code: (ii) x, y, z1/2.
 

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