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The title compound, C12H13NO3, was synthesized from L-β-threonine, and the lactone ring was formed by nucleophilic reaction of the β-hydroxyl group in the presence of a base. The methyl and amino groups are located at cis positions, but the puckering of the lactone ring reduces their steric hindrance. The benzoyl π-electrons and amide bond were expected to conjugate to each other, but their least-square planes are inclined at 26.3 (1)°. The hydrogen bonds between the amide bonds extend along the b axis and stabilize the molecular packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019883/ac6057sup1.cif
Contains datablocks bthr, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019883/ac6057Isup2.hkl
Contains datablock I

CCDC reference: 225719

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.117
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.843 0.997 Tmin' and Tmax expected: 0.952 0.997 RR' = 0.886 Please check that your absorption correction is appropriate. STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.100 From the CIF: _refine_ls_abs_structure_Flack_su 1.600 PLAT032_ALERT_4_C Std Uncertainty in Flack Parameter too High .... 1.60 PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.61 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 27.86 From the CIF: _reflns_number_total 1385 Count of symmetry unique reflns 1418 Completeness (_total/calc) 97.67% 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
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PARST (Nardelli, 1983).

L-β-threonine lactone analogue top
Crystal data top
C12H13NO3F(000) = 232
Mr = 219.23Dx = 1.364 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.521 (1) ÅCell parameters from 2050 reflections
b = 5.1143 (6) Åθ = 2.4–28.3°
c = 12.401 (2) ŵ = 0.10 mm1
β = 99.098 (2)°T = 120 K
V = 533.6 (1) Å3Needle, colourless
Z = 20.50 × 0.06 × 0.03 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1385 independent reflections
Radiation source: MacScience, M18XCE rotating anode1339 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.366 pixels mm-1θmax = 27.9°, θmin = 1.7°
ω–scanh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 66
Tmin = 0.843, Tmax = 0.997l = 1616
4798 measured reflections
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0819P)2 + 0.0481P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
1385 reflectionsΔρmax = 0.40 e Å3
146 parametersΔρmin = 0.16 e Å3
1 restraintAbsolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (16)
Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.4095 (0.0066) x - 2.9265 (0.0048) y + 2.5256 (0.0123) z = 2.7150 (0.0066)

* 0.0054 (0.0017) C11 * -0.0075 (0.0018) C12 * 0.0032 (0.0018) C13 * 0.0033 (0.0019) C14 * -0.0054 (0.0021) C15 * 0.0011 (0.0019) C16

Rms deviation of fitted atoms = 0.0048

7.9709 (0.0023) x - 0.7992 (0.0054) y + 2.0477 (0.0098) z = 2.9788 (0.0029)

Angle to previous plane (with approximate e.s.d.) = 26.28 (0.11)

* 0.0075 (0.0010) C11 * -0.0023 (0.0018) C17 * -0.0025 (0.0007) O17 * -0.0127 (0.0014) N1 * 0.0100 (0.0010) C1A

Rms deviation of fitted atoms = 0.0081

5.7289 (0.0073) x - 3.6501 (0.0042) y - 3.7238 (0.0127) z = 0.5615 (0.0033)

Angle to previous plane (with approximate e.s.d.) = 47.30 (0.09)

* 0.1757 (0.0014) C1A * -0.1476 (0.0013) C2B * 0.0615 (0.0014) O3G * 0.0539 (0.0014) C5 * -0.1436 (0.0014) C4B 0.1712 (0.0035) O5 - 1.5442 (0.0034) C3G

Rms deviation of fitted atoms = 0.1265

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
C110.2577 (2)0.0418 (5)0.47163 (17)0.0178 (4)
C120.3287 (3)0.2528 (6)0.53074 (18)0.0243 (5)
H10.39300.37080.49780.029*
C130.3057 (3)0.2915 (6)0.63838 (19)0.0307 (6)
H20.35580.43410.67930.037*
C140.2099 (3)0.1224 (6)0.68542 (18)0.0321 (6)
H30.19410.14900.75880.039*
C150.1367 (4)0.0862 (6)0.6262 (2)0.0371 (7)
H40.06990.20080.65870.045*
C160.1609 (3)0.1277 (5)0.5190 (2)0.0294 (5)
H50.11150.27140.47850.035*
C170.2804 (2)0.0139 (4)0.35645 (16)0.0164 (4)
O170.2676 (2)0.2382 (3)0.31889 (13)0.0225 (4)
N10.3150 (2)0.1897 (4)0.29617 (14)0.0167 (4)
H60.32120.34840.32390.020*
C1A0.3422 (2)0.1467 (4)0.18473 (15)0.0154 (4)
H70.42020.00060.18460.018*
C2B0.1896 (3)0.0788 (5)0.10329 (16)0.0199 (5)
H80.17740.11550.09840.024*
O3G0.22233 (18)0.1791 (4)0.00082 (11)0.0237 (4)
C3G0.0385 (3)0.1974 (6)0.12968 (19)0.0277 (5)
H90.05600.38300.14720.042*
H100.00700.10660.19250.042*
H110.04580.17970.06650.042*
C4B0.4059 (3)0.3862 (5)0.13356 (16)0.0189 (4)
H120.36600.54910.16280.023*
H130.52350.38860.14670.023*
C50.3422 (3)0.3549 (5)0.01343 (18)0.0211 (5)
O50.3829 (2)0.4643 (4)0.06277 (13)0.0318 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0199 (9)0.0187 (10)0.0153 (9)0.0042 (8)0.0047 (7)0.0007 (8)
C120.0243 (10)0.0306 (12)0.0183 (9)0.0030 (10)0.0041 (8)0.0040 (10)
C130.0308 (11)0.0418 (16)0.0185 (10)0.0030 (11)0.0003 (9)0.0084 (11)
C140.0366 (13)0.0460 (17)0.0146 (10)0.0104 (12)0.0068 (9)0.0005 (11)
C150.0511 (16)0.0389 (16)0.0264 (12)0.0038 (13)0.0216 (11)0.0046 (12)
C160.0397 (13)0.0259 (12)0.0250 (11)0.0045 (12)0.0129 (10)0.0002 (11)
C170.0180 (9)0.0156 (10)0.0165 (9)0.0005 (8)0.0053 (7)0.0009 (8)
O170.0337 (8)0.0147 (7)0.0211 (8)0.0003 (7)0.0103 (6)0.0019 (7)
N10.0260 (8)0.0117 (8)0.0136 (8)0.0002 (7)0.0065 (6)0.0018 (6)
C1A0.0225 (10)0.0119 (9)0.0130 (8)0.0010 (8)0.0070 (7)0.0023 (8)
C2B0.0265 (11)0.0190 (10)0.0148 (9)0.0063 (9)0.0056 (8)0.0001 (8)
O3G0.0297 (8)0.0285 (9)0.0139 (7)0.0050 (8)0.0064 (6)0.0013 (7)
C3G0.0218 (10)0.0373 (14)0.0247 (10)0.0011 (11)0.0056 (8)0.0046 (11)
C4B0.0268 (10)0.0140 (9)0.0174 (9)0.0018 (8)0.0083 (8)0.0013 (8)
C50.0257 (10)0.0216 (10)0.0180 (9)0.0018 (9)0.0097 (8)0.0016 (8)
O50.0414 (10)0.0354 (11)0.0213 (8)0.0047 (8)0.0136 (7)0.0064 (8)
Geometric parameters (Å, º) top
C11—C121.388 (3)N1—H60.8800
C11—C161.389 (3)C1A—C4B1.519 (3)
C11—C171.499 (3)C1A—C2B1.554 (3)
C12—C131.394 (3)C1A—H71.0000
C12—H10.9500C2B—O3G1.457 (2)
C13—C141.380 (4)C2B—C3G1.505 (3)
C13—H20.9500C2B—H81.0000
C14—C151.386 (4)O3G—C51.351 (3)
C14—H30.9500C3G—H90.9800
C15—C161.393 (3)C3G—H100.9800
C15—H40.9500C3G—H110.9800
C16—H50.9500C4B—C51.511 (3)
C17—O171.236 (3)C4B—H120.9900
C17—N11.342 (3)C4B—H130.9900
N1—C1A1.454 (2)C5—O51.196 (3)
C12—C11—C16120.0 (2)C4B—C1A—C2B103.1 (2)
C12—C11—C17122.7 (2)N1—C1A—H7108.7
C16—C11—C17117.4 (2)C4B—C1A—H7108.7
C11—C12—C13120.0 (2)C2B—C1A—H7108.7
C11—C12—H1120.0O3G—C2B—C3G109.9 (2)
C13—C12—H1120.0O3G—C2B—C1A103.9 (2)
C14—C13—C12119.9 (2)C3G—C2B—C1A115.2 (2)
C14—C13—H2120.1O3G—C2B—H8109.2
C12—C13—H2120.1C3G—C2B—H8109.2
C13—C14—C15120.3 (2)C1A—C2B—H8109.2
C13—C14—H3119.8C5—O3G—C2B111.4 (2)
C15—C14—H3119.8C2B—C3G—H9109.5
C14—C15—C16120.0 (2)C2B—C3G—H10109.5
C14—C15—H4120.0H9—C3G—H10109.5
C16—C15—H4120.0C2B—C3G—H11109.5
C11—C16—C15119.7 (2)H9—C3G—H11109.5
C11—C16—H5120.1H10—C3G—H11109.5
C15—C16—H5120.1C5—C4B—C1A103.3 (2)
O17—C17—N1121.6 (2)C5—C4B—H12111.1
O17—C17—C11121.2 (2)C1A—C4B—H12111.1
N1—C17—C11117.2 (2)C5—C4B—H13111.1
C17—N1—C1A119.6 (2)C1A—C4B—H13111.1
C17—N1—H6120.2H12—C4B—H13109.1
C1A—N1—H6120.2O5—C5—O3G121.0 (2)
N1—C1A—C4B113.3 (2)O5—C5—C4B128.8 (2)
N1—C1A—C2B114.1 (2)O3G—C5—C4B110.2 (2)
C16—C11—C12—C131.3 (4)C17—N1—C1A—C4B170.66 (18)
C17—C11—C12—C13178.7 (2)C17—N1—C1A—C2B71.8 (2)
C11—C12—C13—C141.1 (4)N1—C1A—C2B—O3G150.75 (17)
C12—C13—C14—C150.1 (4)C4B—C1A—C2B—O3G27.4 (2)
C13—C14—C15—C160.7 (4)N1—C1A—C2B—C3G30.5 (3)
C12—C11—C16—C150.5 (4)C4B—C1A—C2B—C3G92.9 (2)
C17—C11—C16—C15179.5 (2)C3G—C2B—O3G—C5105.5 (2)
C14—C15—C16—C110.5 (4)C1A—C2B—O3G—C518.2 (2)
C12—C11—C17—O17153.7 (2)N1—C1A—C4B—C5150.28 (18)
C16—C11—C17—O1726.3 (3)C2B—C1A—C4B—C526.4 (2)
C12—C11—C17—N126.4 (3)C2B—O3G—C5—O5177.8 (2)
C16—C11—C17—N1153.6 (2)C2B—O3G—C5—C4B1.1 (3)
O17—C17—N1—C1A1.6 (3)C1A—C4B—C5—O5164.4 (2)
C11—C17—N1—C1A178.53 (18)C1A—C4B—C5—O3G16.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H6···O17i0.882.162.973 (3)153
Symmetry code: (i) x, y+1, z.
 

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