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The title compound, C13H18O2N2, was isolated during the preparation of new chiral auxiliaries. Notably, this compound is unlike previously reported structures in that it does not contain an imide moiety. The crystal structure indicates the presence of intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401829X/cv6344sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401829X/cv6344Isup2.hkl
Contains datablock I

CCDC reference: 251634

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.088
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C30 - C31 .. 15.13 su
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.71 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.31 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.37 From the CIF: _reflns_number_total 2857 Count of symmetry unique reflns 2871 Completeness (_total/calc) 99.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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 publication routines (Farrugia, 1999).

3,4,5,6-tetrahydro-5-methyl-6-phenyl-4-propyl-2H-1,3,4-oxadiazin-2-one top
Crystal data top
C13H18N2O2F(000) = 504
Mr = 234.29Dx = 1.184 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7993 reflections
a = 7.7432 (4) Åθ = 2.5–26.4°
b = 8.8457 (4) ŵ = 0.08 mm1
c = 19.2021 (9) ÅT = 193 K
β = 91.690 (1)°Prism, colorless
V = 1314.66 (11) Å30.71 × 0.4 × 0.39 mm
Z = 4
Data collection top
Bruker PLATFORM
diffractometer/SMART 1000 CCD area-detector
2857 independent reflections
Graphite monochromator2780 reflections with I > 2σ(I)
Detector resolution: 8.192 pixels mm-1Rint = 0.014
ω scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.945, Tmax = 0.969k = 1110
9368 measured reflectionsl = 2323
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.057P)2 + 0.105P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2857 reflectionsΔρmax = 0.24 e Å3
316 parametersΔρmin = 0.14 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.043 (4)
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
O10.16622 (16)0.90543 (15)0.43843 (6)0.0380 (3)
C20.1198 (2)0.9184 (2)0.37031 (8)0.0333 (3)
N30.00181 (18)0.82339 (18)0.34310 (8)0.0362 (3)
N40.07999 (18)0.70366 (17)0.37888 (7)0.0334 (3)
C50.0326 (2)0.65601 (19)0.43709 (9)0.0352 (4)
H50.03520.58620.46680.042*
C60.0833 (2)0.7940 (2)0.48161 (8)0.0339 (3)
H60.0250.83980.49930.041*
C70.2016 (2)0.7611 (2)0.54330 (9)0.0367 (4)
C80.3809 (2)0.7632 (3)0.53904 (11)0.0500 (5)
H80.4330.79440.49730.06*
C90.4830 (3)0.7194 (3)0.59621 (12)0.0568 (5)
H90.60520.71970.5930.068*
C100.4099 (3)0.6757 (3)0.65732 (11)0.0527 (5)
H100.48110.64530.6960.063*
C110.2325 (3)0.6763 (3)0.66226 (10)0.0483 (4)
H110.18120.64720.70460.058*
C120.1288 (2)0.7193 (2)0.60545 (9)0.0390 (4)
H120.00670.720.60920.047*
C130.1863 (2)0.5676 (2)0.41041 (11)0.0440 (4)
H13A0.14450.48130.38270.066*
H13B0.25720.5310.450.066*
H13C0.2560.63360.38140.066*
C140.2550 (2)0.7503 (2)0.39830 (9)0.0408 (4)
H14A0.24860.84920.42240.049*
H14B0.30220.67540.4310.049*
C150.3748 (2)0.7631 (3)0.33466 (11)0.0463 (4)
H15A0.48950.79830.34940.056*
H15B0.32840.83990.30270.056*
C160.3962 (3)0.6160 (4)0.29622 (18)0.0794 (9)
H16A0.47340.63070.25540.119*
H16B0.44580.54030.32710.119*
H16C0.28320.5810.2810.119*
O170.19170 (16)1.01600 (16)0.33654 (6)0.0411 (3)
O210.05307 (15)0.89839 (17)0.09450 (6)0.0421 (3)
C220.0419 (2)0.9282 (2)0.16300 (9)0.0372 (4)
N230.1481 (2)1.0310 (2)0.19260 (8)0.0422 (4)
N240.2848 (2)1.10798 (18)0.15901 (8)0.0401 (3)
C250.3347 (2)1.0209 (2)0.09827 (9)0.0414 (4)
H250.41151.08620.070.05*
C260.1728 (2)0.9843 (2)0.05317 (9)0.0409 (4)
H260.1161.08160.0390.049*
C270.2058 (2)0.8940 (3)0.01158 (9)0.0481 (5)
C280.2051 (2)0.7367 (3)0.01210 (11)0.0512 (5)
H280.17870.68380.02930.061*
C290.2419 (3)0.6558 (4)0.07119 (12)0.0647 (7)
H290.23970.54850.070.078*
C300.2808 (3)0.7275 (5)0.13038 (14)0.0740 (9)
H300.30740.67050.17060.089*
C310.2822 (3)0.8807 (6)0.13299 (12)0.0851 (12)
H310.30880.93030.17520.102*
C320.2438 (3)0.9688 (4)0.07221 (12)0.0678 (7)
H320.24461.07620.07390.081*
C330.4381 (3)0.8819 (3)0.12081 (11)0.0497 (5)
H33A0.53910.91330.14920.075*
H33B0.47640.82780.07950.075*
H33C0.36540.81510.14820.075*
C340.2334 (2)1.2654 (2)0.14430 (10)0.0441 (4)
H34A0.12361.26560.11660.053*
H34B0.32261.31410.1160.053*
C350.2106 (3)1.3556 (3)0.20965 (12)0.0572 (5)
H35A0.31731.34860.23920.069*
H35B0.11481.31180.23610.069*
C360.1716 (4)1.5207 (3)0.19444 (16)0.0703 (7)
H36A0.15751.57510.23840.105*
H36B0.06491.52830.16590.105*
H36C0.26731.56520.16920.105*
O370.06392 (17)0.85737 (17)0.19606 (6)0.0443 (3)
H30.017 (2)0.829 (3)0.3007 (11)0.036 (5)*
H230.162 (3)1.029 (3)0.2382 (12)0.040 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0455 (7)0.0339 (6)0.0346 (6)0.0088 (5)0.0016 (5)0.0008 (5)
C20.0323 (8)0.0323 (8)0.0354 (8)0.0011 (7)0.0015 (6)0.0016 (7)
N30.0384 (7)0.0382 (8)0.0320 (7)0.0090 (6)0.0007 (5)0.0023 (6)
N40.0328 (7)0.0312 (7)0.0364 (7)0.0055 (6)0.0032 (5)0.0007 (5)
C50.0364 (8)0.0309 (8)0.0384 (8)0.0026 (7)0.0037 (6)0.0019 (7)
C60.0339 (8)0.0332 (8)0.0347 (7)0.0008 (7)0.0038 (6)0.0003 (7)
C70.0384 (8)0.0336 (8)0.0379 (8)0.0011 (7)0.0012 (6)0.0019 (7)
C80.0390 (9)0.0600 (13)0.0509 (10)0.0016 (9)0.0014 (8)0.0086 (10)
C90.0395 (10)0.0636 (14)0.0666 (13)0.0023 (10)0.0095 (9)0.0068 (11)
C100.0571 (12)0.0464 (11)0.0534 (11)0.0000 (10)0.0219 (9)0.0045 (9)
C110.0615 (12)0.0457 (10)0.0372 (9)0.0040 (9)0.0054 (8)0.0020 (8)
C120.0416 (9)0.0364 (9)0.0389 (9)0.0007 (7)0.0005 (7)0.0005 (7)
C130.0438 (9)0.0367 (9)0.0518 (10)0.0033 (8)0.0068 (8)0.0022 (8)
C140.0343 (8)0.0435 (10)0.0449 (9)0.0040 (7)0.0046 (7)0.0052 (8)
C150.0352 (9)0.0491 (11)0.0544 (11)0.0057 (8)0.0019 (7)0.0009 (9)
C160.0566 (13)0.0805 (19)0.099 (2)0.0006 (14)0.0270 (13)0.0390 (17)
O170.0424 (6)0.0424 (7)0.0383 (6)0.0123 (6)0.0001 (5)0.0040 (5)
O210.0364 (6)0.0529 (8)0.0371 (6)0.0111 (6)0.0019 (5)0.0013 (6)
C220.0356 (8)0.0384 (9)0.0373 (8)0.0028 (7)0.0012 (6)0.0033 (7)
N230.0502 (9)0.0427 (8)0.0337 (8)0.0137 (7)0.0007 (6)0.0047 (7)
N240.0393 (7)0.0374 (8)0.0433 (8)0.0098 (6)0.0043 (6)0.0080 (6)
C250.0350 (8)0.0465 (10)0.0423 (9)0.0072 (8)0.0038 (7)0.0082 (8)
C260.0327 (8)0.0490 (11)0.0410 (9)0.0047 (8)0.0007 (7)0.0060 (8)
C270.0297 (8)0.0760 (15)0.0383 (9)0.0023 (9)0.0012 (7)0.0032 (9)
C280.0356 (10)0.0707 (15)0.0471 (11)0.0026 (9)0.0004 (8)0.0091 (10)
C290.0359 (10)0.097 (2)0.0608 (13)0.0071 (11)0.0054 (9)0.0246 (13)
C300.0504 (13)0.118 (3)0.0530 (14)0.0212 (15)0.0028 (10)0.0110 (15)
C310.0517 (13)0.165 (4)0.0389 (11)0.0135 (19)0.0076 (9)0.0278 (17)
C320.0503 (12)0.103 (2)0.0496 (12)0.0015 (13)0.0019 (9)0.0214 (13)
C330.0408 (9)0.0490 (11)0.0588 (11)0.0021 (9)0.0080 (8)0.0047 (9)
C340.0408 (9)0.0407 (10)0.0503 (10)0.0080 (8)0.0069 (8)0.0100 (8)
C350.0691 (14)0.0429 (11)0.0585 (12)0.0047 (10)0.0141 (10)0.0011 (9)
C360.0782 (17)0.0450 (12)0.0857 (17)0.0000 (12)0.0298 (13)0.0026 (12)
O370.0431 (6)0.0487 (7)0.0413 (6)0.0124 (6)0.0034 (5)0.0029 (6)
Geometric parameters (Å, º) top
O1—C21.351 (2)O21—C221.347 (2)
O1—C61.450 (2)O21—C261.452 (2)
C2—O171.223 (2)C22—O371.224 (2)
C2—N31.337 (2)C22—N231.342 (2)
N3—N41.4215 (19)N23—N241.428 (2)
N3—H30.82 (2)N23—H230.88 (2)
N4—C51.459 (2)N24—C251.459 (3)
N4—C141.475 (2)N24—C341.473 (3)
C5—C131.525 (2)C25—C331.524 (3)
C5—C61.534 (2)C25—C261.537 (2)
C5—H51C25—H251
C6—C71.504 (2)C26—C271.506 (3)
C6—H61C26—H261
C7—C121.385 (2)C27—C321.378 (3)
C7—C81.393 (3)C27—C281.391 (4)
C8—C91.389 (3)C28—C291.378 (3)
C8—H80.95C28—H280.95
C9—C101.373 (3)C29—C301.343 (4)
C9—H90.95C29—H290.95
C10—C111.380 (3)C30—C311.356 (6)
C10—H100.95C30—H300.95
C11—C121.388 (3)C31—C321.442 (5)
C11—H110.95C31—H310.95
C12—H120.95C32—H320.95
C13—H13A0.98C33—H33A0.98
C13—H13B0.98C33—H33B0.98
C13—H13C0.98C33—H33C0.98
C14—C151.517 (3)C34—C351.502 (3)
C14—H14A0.99C34—H34A0.99
C14—H14B0.99C34—H34B0.99
C15—C161.503 (4)C35—C361.517 (4)
C15—H15A0.99C35—H35A0.99
C15—H15B0.99C35—H35B0.99
C16—H16A0.98C36—H36A0.98
C16—H16B0.98C36—H36B0.98
C16—H16C0.98C36—H36C0.98
C2—O1—C6120.12 (13)C22—O21—C26119.45 (14)
O17—C2—N3123.58 (15)O37—C22—N23122.60 (16)
O17—C2—O1117.46 (15)O37—C22—O21118.03 (16)
N3—C2—O1118.94 (15)N23—C22—O21119.35 (15)
C2—N3—N4126.09 (14)C22—N23—N24125.80 (15)
C2—N3—H3116.4 (15)C22—N23—H23117.3 (15)
N4—N3—H3117.1 (16)N24—N23—H23113.2 (14)
N3—N4—C5108.70 (12)N23—N24—C25109.08 (14)
N3—N4—C14109.84 (14)N23—N24—C34109.72 (15)
C5—N4—C14114.82 (13)C25—N24—C34114.96 (15)
N4—C5—C13110.20 (14)N24—C25—C33110.38 (15)
N4—C5—C6109.53 (14)N24—C25—C26109.31 (15)
C13—C5—C6113.94 (15)C33—C25—C26113.77 (17)
N4—C5—H5107.6N24—C25—H25107.7
C13—C5—H5107.6C33—C25—H25107.7
C6—C5—H5107.6C26—C25—H25107.7
O1—C6—C7108.18 (13)O21—C26—C27107.46 (16)
O1—C6—C5109.42 (12)O21—C26—C25109.00 (14)
C7—C6—C5115.13 (15)C27—C26—C25114.92 (15)
O1—C6—H6108O21—C26—H26108.4
C7—C6—H6108C27—C26—H26108.4
C5—C6—H6108C25—C26—H26108.4
C12—C7—C8119.06 (16)C32—C27—C28118.3 (2)
C12—C7—C6118.43 (15)C32—C27—C26119.2 (2)
C8—C7—C6122.41 (15)C28—C27—C26122.38 (19)
C9—C8—C7119.68 (19)C29—C28—C27121.6 (2)
C9—C8—H8120.2C29—C28—H28119.2
C7—C8—H8120.2C27—C28—H28119.2
C10—C9—C8120.9 (2)C30—C29—C28120.6 (3)
C10—C9—H9119.5C30—C29—H29119.7
C8—C9—H9119.5C28—C29—H29119.7
C9—C10—C11119.61 (18)C29—C30—C31120.3 (3)
C9—C10—H10120.2C29—C30—H30119.8
C11—C10—H10120.2C31—C30—H30119.8
C10—C11—C12120.05 (18)C30—C31—C32120.6 (3)
C10—C11—H11120C30—C31—H31119.7
C12—C11—H11120C32—C31—H31119.7
C7—C12—C11120.63 (18)C27—C32—C31118.6 (3)
C7—C12—H12119.7C27—C32—H32120.7
C11—C12—H12119.7C31—C32—H32120.7
C5—C13—H13A109.5C25—C33—H33A109.5
C5—C13—H13B109.5C25—C33—H33B109.5
H13A—C13—H13B109.5H33A—C33—H33B109.5
C5—C13—H13C109.5C25—C33—H33C109.5
H13A—C13—H13C109.5H33A—C33—H33C109.5
H13B—C13—H13C109.5H33B—C33—H33C109.5
N4—C14—C15111.21 (15)N24—C34—C35112.33 (16)
N4—C14—H14A109.4N24—C34—H34A109.1
C15—C14—H14A109.4C35—C34—H34A109.1
N4—C14—H14B109.4N24—C34—H34B109.1
C15—C14—H14B109.4C35—C34—H34B109.1
H14A—C14—H14B108H34A—C34—H34B107.9
C16—C15—C14112.8 (2)C34—C35—C36112.2 (2)
C16—C15—H15A109C34—C35—H35A109.2
C14—C15—H15A109C36—C35—H35A109.2
C16—C15—H15B109C34—C35—H35B109.2
C14—C15—H15B109C36—C35—H35B109.2
H15A—C15—H15B107.8H35A—C35—H35B107.9
C15—C16—H16A109.5C35—C36—H36A109.5
C15—C16—H16B109.5C35—C36—H36B109.5
H16A—C16—H16B109.5H36A—C36—H36B109.5
C15—C16—H16C109.5C35—C36—H36C109.5
H16A—C16—H16C109.5H36A—C36—H36C109.5
H16B—C16—H16C109.5H36B—C36—H36C109.5
C6—O1—C2—O17178.77 (15)C26—O21—C22—O37177.72 (16)
C6—O1—C2—N32.6 (2)C26—O21—C22—N233.5 (3)
O17—C2—N3—N4176.91 (16)O37—C22—N23—N24174.01 (18)
O1—C2—N3—N41.7 (2)O21—C22—N23—N244.7 (3)
C2—N3—N4—C525.2 (2)C22—N23—N24—C2521.3 (2)
C2—N3—N4—C14101.20 (19)C22—N23—N24—C34105.5 (2)
N3—N4—C5—C1373.38 (17)N23—N24—C25—C3374.51 (18)
C14—N4—C5—C13163.16 (15)C34—N24—C25—C33161.79 (15)
N3—N4—C5—C652.72 (16)N23—N24—C25—C2651.34 (19)
C14—N4—C5—C670.74 (18)C34—N24—C25—C2672.35 (19)
C2—O1—C6—C7157.74 (14)C22—O21—C26—C27159.87 (15)
C2—O1—C6—C531.6 (2)C22—O21—C26—C2534.7 (2)
N4—C5—C6—O157.26 (16)N24—C25—C26—O2159.2 (2)
C13—C5—C6—O166.67 (18)C33—C25—C26—O2164.7 (2)
N4—C5—C6—C7179.32 (13)N24—C25—C26—C27179.89 (16)
C13—C5—C6—C755.38 (19)C33—C25—C26—C2756.0 (2)
O1—C6—C7—C12150.04 (16)O21—C26—C27—C32150.11 (17)
C5—C6—C7—C1287.23 (19)C25—C26—C27—C3288.4 (2)
O1—C6—C7—C833.5 (2)O21—C26—C27—C2832.1 (2)
C5—C6—C7—C889.2 (2)C25—C26—C27—C2889.4 (2)
C12—C7—C8—C91.9 (3)C32—C27—C28—C290.2 (3)
C6—C7—C8—C9174.6 (2)C26—C27—C28—C29177.56 (16)
C7—C8—C9—C100.8 (4)C27—C28—C29—C300.4 (3)
C8—C9—C10—C110.4 (4)C28—C29—C30—C310.8 (4)
C9—C10—C11—C120.7 (3)C29—C30—C31—C320.6 (5)
C8—C7—C12—C111.6 (3)C28—C27—C32—C310.4 (3)
C6—C7—C12—C11174.92 (18)C26—C27—C32—C31177.4 (2)
C10—C11—C12—C70.4 (3)C30—C31—C32—C270.0 (4)
N3—N4—C14—C1570.20 (19)N23—N24—C34—C3565.63 (19)
C5—N4—C14—C15166.94 (15)C25—N24—C34—C35171.01 (16)
N4—C14—C15—C1660.9 (2)N24—C34—C35—C36175.47 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O370.82 (2)2.05 (2)2.870 (2)177 (2)
N23—H23···O170.88 (2)1.90 (2)2.778 (2)178 (2)
 

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