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In the title compound, C12H13NO3, the angles at the Csp3 atoms in the vicinity of the morpholine ring are slightly strained, as indicated by the values of 113.08 (13) and 115.18 (14)° for C-C-C angles and 106.98 (13)° for the N-C-C angle.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501682X/lh6437sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501682X/lh6437Isup2.hkl
Contains datablock I

CCDC reference: 277716

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.087
  • Data-to-parameter ratio = 9.9

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.54 Ang.
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 28.05 From the CIF: _reflns_number_total 1454 Count of symmetry unique reflns 1454 Completeness (_total/calc) 100.00% 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 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 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 (Bruker, 1997); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(5S,6R)-4,5-Dimethyl-6-phenylmorpholine-2,3-dione top
Crystal data top
C12H13NO3F(000) = 232.0
Mr = 219.23Dx = 1.315 Mg m3
Monoclinic, P21Melting point: 455 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 7.3829 (11) ÅCell parameters from 1600 reflections
b = 6.7658 (10) Åθ = 3.4–26.6°
c = 11.1074 (17) ŵ = 0.10 mm1
β = 93.826 (2)°T = 293 K
V = 553.59 (14) Å3Prism, colourless
Z = 20.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1454 independent reflections
Radiation source: fine-focus sealed tube1263 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 28.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 97
Tmin = 0.976, Tmax = 0.981k = 88
3758 measured reflectionsl = 1414
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.048P)2 + 0.0289P]
where P = (Fo2 + 2Fc2)/3
1454 reflections(Δ/σ)max = 0.002
147 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.14 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
N10.72529 (19)0.1308 (3)0.94829 (11)0.0455 (3)
O10.46611 (15)0.2184 (2)0.75940 (11)0.0493 (3)
O20.25547 (17)0.1225 (3)0.87707 (14)0.0725 (5)
O30.4986 (2)0.1340 (3)1.07541 (11)0.0706 (4)
C10.4113 (2)0.1611 (3)0.86604 (17)0.0498 (4)
C20.5524 (3)0.1420 (3)0.97386 (15)0.0488 (4)
C30.7766 (2)0.1324 (3)0.82228 (13)0.0406 (4)
H30.90160.18080.82200.049*
C40.6543 (2)0.2808 (3)0.75485 (15)0.0403 (4)
H40.66930.40960.79460.048*
C50.8655 (3)0.0976 (5)1.04538 (16)0.0656 (6)
H5A0.84600.18501.11140.098*
H5B0.98280.12291.01610.098*
H5C0.86000.03691.07240.098*
C60.7715 (3)0.0753 (3)0.77006 (17)0.0508 (4)
H6A0.84560.16110.82150.076*
H6B0.81690.07310.69110.076*
H6C0.64870.12280.76460.076*
C70.6949 (2)0.3030 (3)0.62424 (14)0.0387 (4)
C80.8231 (2)0.4407 (3)0.59481 (16)0.0484 (4)
H80.87840.52030.65480.058*
C90.8699 (3)0.4612 (3)0.47690 (17)0.0567 (5)
H90.95630.55420.45800.068*
C100.7889 (3)0.3446 (3)0.38792 (16)0.0531 (5)
H100.82010.35890.30860.064*
C110.6619 (3)0.2068 (4)0.41564 (16)0.0532 (5)
H110.60820.12700.35520.064*
C120.6131 (2)0.1859 (3)0.53392 (15)0.0474 (4)
H120.52580.09360.55220.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0511 (8)0.0502 (8)0.0359 (6)0.0041 (8)0.0084 (5)0.0014 (7)
O10.0369 (6)0.0629 (8)0.0492 (6)0.0048 (6)0.0120 (5)0.0014 (6)
O20.0444 (7)0.0930 (12)0.0833 (10)0.0023 (9)0.0289 (7)0.0024 (11)
O30.0866 (10)0.0799 (11)0.0494 (7)0.0056 (10)0.0340 (7)0.0007 (8)
C10.0457 (9)0.0511 (11)0.0552 (9)0.0017 (8)0.0224 (7)0.0050 (9)
C20.0611 (10)0.0428 (9)0.0447 (8)0.0043 (10)0.0200 (7)0.0027 (8)
C30.0371 (7)0.0491 (9)0.0365 (7)0.0028 (8)0.0089 (6)0.0004 (8)
C40.0395 (8)0.0412 (9)0.0414 (8)0.0009 (7)0.0116 (6)0.0036 (7)
C50.0683 (12)0.0859 (18)0.0420 (9)0.0145 (12)0.0010 (8)0.0061 (11)
C60.0573 (11)0.0484 (10)0.0476 (9)0.0110 (9)0.0111 (8)0.0002 (8)
C70.0387 (8)0.0382 (8)0.0399 (8)0.0038 (7)0.0087 (6)0.0014 (7)
C80.0518 (10)0.0447 (9)0.0496 (9)0.0067 (9)0.0107 (8)0.0045 (8)
C90.0586 (11)0.0545 (12)0.0594 (11)0.0094 (10)0.0217 (9)0.0047 (10)
C100.0544 (10)0.0654 (13)0.0410 (8)0.0056 (10)0.0145 (7)0.0064 (9)
C110.0538 (10)0.0640 (12)0.0413 (8)0.0045 (10)0.0002 (8)0.0032 (9)
C120.0452 (9)0.0522 (12)0.0451 (8)0.0080 (8)0.0047 (7)0.0016 (8)
Geometric parameters (Å, º) top
N1—C21.328 (2)C5—H5C0.9600
N1—C51.462 (2)C6—H6A0.9600
N1—C31.4741 (18)C6—H6B0.9600
O1—C11.335 (2)C6—H6C0.9600
O1—C41.4564 (19)C7—C81.383 (2)
O2—C11.194 (2)C7—C121.385 (2)
O3—C21.2217 (19)C8—C91.383 (2)
C1—C21.539 (3)C8—H80.9300
C3—C41.514 (3)C9—C101.370 (3)
C3—C61.519 (3)C9—H90.9300
C3—H30.9800C10—C111.372 (3)
C4—C71.508 (2)C10—H100.9300
C4—H40.9800C11—C121.392 (2)
C5—H5A0.9600C11—H110.9300
C5—H5B0.9600C12—H120.9300
C2—N1—C5119.65 (15)H5A—C5—H5C109.5
C2—N1—C3120.93 (14)H5B—C5—H5C109.5
C5—N1—C3119.17 (14)C3—C6—H6A109.5
C1—O1—C4117.50 (13)C3—C6—H6B109.5
O2—C1—O1120.41 (18)H6A—C6—H6B109.5
O2—C1—C2120.57 (16)C3—C6—H6C109.5
O1—C1—C2119.02 (14)H6A—C6—H6C109.5
O3—C2—N1124.82 (19)H6B—C6—H6C109.5
O3—C2—C1118.51 (16)C8—C7—C12119.10 (15)
N1—C2—C1116.65 (14)C8—C7—C4118.53 (14)
N1—C3—C4106.98 (13)C12—C7—C4122.33 (15)
N1—C3—C6110.76 (15)C7—C8—C9120.62 (17)
C4—C3—C6115.18 (14)C7—C8—H8119.7
N1—C3—H3107.9C9—C8—H8119.7
C4—C3—H3107.9C10—C9—C8120.05 (18)
O1—C4—C7108.27 (12)C10—C9—H9120.0
O1—C4—C3109.22 (14)C8—C9—H9120.0
C6—C3—H3107.9C9—C10—C11120.08 (17)
C7—C4—C3113.08 (13)C9—C10—H10120.0
O1—C4—H4108.7C11—C10—H10120.0
C7—C4—H4108.7C10—C11—C12120.29 (18)
C3—C4—H4108.7C10—C11—H11119.9
N1—C5—H5A109.5C12—C11—H11119.9
N1—C5—H5B109.5C7—C12—C11119.86 (17)
H5A—C5—H5B109.5C7—C12—H12120.1
N1—C5—H5C109.5C11—C12—H12120.1
C4—O1—C1—O2174.43 (19)N1—C3—C4—O161.04 (17)
C4—O1—C1—C26.6 (3)C6—C3—C4—O162.54 (17)
C5—N1—C2—O32.9 (4)N1—C3—C4—C7178.34 (13)
C3—N1—C2—O3177.1 (2)C6—C3—C4—C758.08 (19)
C5—N1—C2—C1175.4 (2)O1—C4—C7—C8150.14 (15)
C3—N1—C2—C11.3 (3)C3—C4—C7—C888.70 (19)
O2—C1—C2—O317.5 (3)O1—C4—C7—C1232.2 (2)
O1—C1—C2—O3163.6 (2)C3—C4—C7—C1288.97 (19)
O2—C1—C2—N1161.0 (2)C12—C7—C8—C90.2 (3)
O1—C1—C2—N117.9 (3)C4—C7—C8—C9177.54 (17)
C2—N1—C3—C439.7 (2)C7—C8—C9—C100.0 (3)
C5—N1—C3—C4146.19 (19)C8—C9—C10—C110.3 (3)
C2—N1—C3—C686.6 (2)C9—C10—C11—C120.7 (3)
C5—N1—C3—C687.5 (2)C8—C7—C12—C110.6 (3)
C1—O1—C4—C7169.92 (15)C4—C7—C12—C11177.04 (16)
C1—O1—C4—C346.4 (2)C10—C11—C12—C70.9 (3)
 

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