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The (S)-4-alkoxo-2-azetidinecarboxylic acids are optically active β-lactam derivatives of aspartic acid, which are used as precursors of carbapenem-type antibiotics and poly-β-aspartates. The crystal structures of three (S)-4-alkoxo-2-azetidinecarboxylic acids with alkyl chains with 10, 12 and 16 C atoms were solved using parallel tempering and refined against the X-ray powder diffraction data using the Rietveld method. The azetidinone rings in the three compounds display a pattern of asymmetrical bond distances and an almost planar conformation; these characteristics are compared with periodic solid-state, gas-phase density-functional theory (DFT) calculations and MOGUL average bond distances and angles from the CSD. The compounds pack along [001] as corrugated sheets separated by approximately 4.40 Å and connected by hydrogen bonds of the type N—H...O.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109036386/kd5033sup1.cif
Contains datablocks KD5033, KD5033_L_10, L_10_phase_2, KD5033_L12, L_12_phase_2, KD5033_L_16

CCDC references: 760240; 760241; 760242

Computing details top

Program(s) used to solve structure: FOX; Favre-Nicolin, V. & Ĉerný, R. (2002). J. Appl. Cryst. 35, 734–743. for KD5033, KD5033_L12, KD5033_L_16. Program(s) used to refine structure: GSAS for KD5033_L_10, KD5033_L12, KD5033_L_16. Molecular graphics: PLATON (Spek, 2003) and DIAMOND 2.1e (Brandenburg, 2001) for KD5033, KD5033_L12, KD5033_L_16. Software used to prepare material for publication: GSAS2CIF (Toby et al., 2003), PLATON (Spek, 2003), and publCIF (Westrip, 2009) for KD5033, KD5033_L12, KD5033_L_16.

(KD5033) top
Crystal data top
a = Åα = °
b = Åβ = °
c = Åγ = °
Refinement top
2 constraints
(KD5033_L_10) (S)-4-decyloxycarbonyl-2-azetidinone top
Crystal data top
C14H25NO3F(000) = 280
Mr = 255.36Dx = 1.102 Mg m3
Monoclinic, P21Melting point: 324 K
Hall symbol: P 2ybµ = 0.08 mm1
a = 27.82406 (16) ÅT = 298 K
b = 5.35267 (4) ÅParticle morphology: needles
c = 5.16992 (3) Åwhite
β = 92.0469 (4)°cylinder, 40 × 1.0 mm
V = 769.48 (1) Å3Specimen preparation: Prepared at 298 K
Z = 2
Data collection top
High Resolution Diffractometer ID31, ESRF, Grenoble, France.Specimen mounting: borosilicate glass capillary
Radiation source: synchrotron, Beamline ID31Data collection mode: transmission
Double crystal Si 111 monochromatorScan method: continuous
Refinement top
Least-squares matrix: fullProfile function: CW Profile function number 4 with 21 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 0.075 #4(GP) = 0.000 #5(LX) = 0.190 #6(ptec) = 0.97 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0030 #11(H/L) = 0.0022 #12(eta) = 0.0000 #13(S400 ) = 2.8E-04 #14(S040 ) = 2.0E-01 #15(S004 ) = 2.2E-01 #16(S220 ) = 1.1E-03 #17(S202 ) = -3.7E-03 #18(S022 ) = 2.7E-01 #19(S301 ) = -1.0E-03 #20(S103 ) = 2.9E-02 #21(S121 ) = -2.8E-02 Peak tails are ignored where the intensity is below 0.0001 times the peak Aniso. broadening axis 0.0 0.0 1.0, CW Profile function number 4 with 16 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 0.000 #4(GP) = 0.000 #5(LX) = 0.592 #6(ptec) = 0.00 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0030 #11(H/L) = 0.0027 #12(eta) = 0.0000 #13(S400 ) = 3.5E-03 #14(S004 ) = 1.2E-03 #15(S220 ) = -2.4E-04 #16(S202 ) = 1.8E-05 Peak tails are ignored where the intensity is below 0.0001 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rp = 0.075193 parameters
Rwp = 0.104122 restraints
Rexp = 0.060(Δ/σ)max = 0.04
R(F2) = 0.08634Background function: GSAS Background function number 1 with 15 terms. Shifted Chebyshev function of 1st kind 1: 121.379 2: -55.7877 3: 24.2590 4: -13.0967 5: 24.8816 6: -30.7740 7: 10.8595 8: 8.05476 9: -9.18279 10: -3.38351 11: 9.67850 12: 0.656338 13: -4.14359 14: 5.76963 15: 1.39635
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.45961 (16)0.636 (3)0.7976 (8)0.1126 (19)*
N20.45533 (17)0.3998 (4)0.7128 (7)0.1126 (19)*
C30.42000 (12)0.3186 (5)0.9022 (7)0.1126 (19)*
C40.42245 (12)0.5923 (5)0.9970 (6)0.1126 (19)*
O50.48089 (18)0.8169 (5)0.7126 (10)0.1126 (19)*
C60.37244 (13)0.2480 (5)0.7751 (8)0.1243 (11)*
O70.34511 (18)0.0931 (6)0.8658 (12)0.1243 (11)*
O80.35795 (14)0.4078 (6)0.5927 (8)0.1243 (11)*
C90.31034 (12)0.3688 (5)0.4752 (7)0.1243 (11)*
C100.29463 (12)0.5970 (5)0.3247 (7)0.1243 (11)*
C110.24668 (12)0.5716 (5)0.1832 (7)0.1243 (11)*
C120.23224 (12)0.8039 (5)0.0377 (7)0.1243 (11)*
C130.18574 (12)0.7758 (5)0.1161 (7)0.1243 (11)*
C140.16767 (12)1.0148 (5)0.2381 (7)0.1243 (11)*
C150.12452 (12)0.9859 (5)0.4178 (7)0.1243 (11)*
C160.10654 (12)1.2327 (5)0.5192 (7)0.1243 (11)*
C170.05908 (12)1.2135 (5)0.6664 (6)0.1243 (11)*
C180.04716 (12)1.4325 (5)0.8396 (7)0.1243 (11)*
H310.4332 (4)0.2013 (6)1.0260 (13)0.156 (3)*
H410.4348 (4)0.6088 (7)1.1719 (9)0.156 (3)*
H420.39320 (19)0.6838 (6)0.964 (3)0.156 (3)*
H910.3112 (6)0.2278 (6)0.3607 (13)0.1442 (13)*
H920.2880 (2)0.3365 (7)0.6086 (11)0.1442 (13)*
H1010.3186 (2)0.6326 (7)0.2009 (12)0.1442 (13)*
H1020.2932 (6)0.7357 (6)0.4420 (13)0.1442 (13)*
H1110.2481 (6)0.4357 (6)0.0626 (13)0.1442 (13)*
H1120.2226 (2)0.5344 (7)0.3058 (12)0.1442 (13)*
H1210.2572 (2)0.8454 (7)0.0785 (13)0.1442 (13)*
H1220.2292 (5)0.9380 (6)0.1593 (12)0.1442 (13)*
H1310.1903 (5)0.6550 (6)0.2502 (11)0.1442 (13)*
H1320.1618 (2)0.7132 (7)0.0038 (13)0.1442 (13)*
H1410.1931 (2)1.0863 (6)0.3348 (15)0.1442 (13)*
H1420.1595 (4)1.1294 (6)0.1038 (11)0.1442 (13)*
H1510.1329 (4)0.8826 (6)0.5610 (11)0.1442 (13)*
H1520.0993 (2)0.9066 (6)0.3260 (15)0.1442 (13)*
H1610.1301 (2)1.3025 (6)0.6297 (13)0.1442 (13)*
H1620.1026 (5)1.3427 (6)0.3748 (11)0.1442 (13)*
H1710.0595 (6)1.0657 (6)0.7716 (14)0.1442 (13)*
H1720.0341 (2)1.1970 (7)0.5440 (12)0.1442 (13)*
H1810.0338 (4)1.3734 (7)1.0022 (10)0.1442 (13)*
H1820.07579 (19)1.5269 (6)0.869 (3)0.1442 (13)*
H1830.0241 (2)1.5368 (6)0.7577 (17)0.1442 (13)*
H210.4638 (5)0.2906 (6)0.5745 (11)0.156 (3)*
Geometric parameters (Å, º) top
C1—N21.340 (18)C11—H1110.960 (6)
C1—C41.504 (6)C11—H1120.960 (7)
C1—O51.226 (15)C12—C111.501 (4)
N2—C11.340 (18)C12—C131.502 (5)
N2—C31.477 (5)C12—H1210.959 (7)
N2—H210.960 (7)C12—H1220.960 (6)
C3—N21.477 (5)C13—C121.502 (5)
C3—C41.546 (4)C13—C141.504 (4)
C3—C61.504 (5)C13—H1310.960 (6)
C3—H310.960 (7)C13—H1320.960 (7)
C4—C11.504 (6)C14—C131.504 (4)
C4—C31.546 (4)C14—C151.500 (5)
C4—H410.960 (6)C14—H1410.960 (7)
C4—H420.960 (6)C14—H1420.959 (6)
O5—C11.226 (15)C15—C141.500 (5)
C6—C31.504 (5)C15—C161.500 (4)
C6—O71.229 (5)C15—H1510.960 (6)
C6—O81.325 (5)C15—H1520.960 (7)
O7—C61.229 (5)C16—C151.500 (4)
O8—C61.325 (5)C16—C171.504 (5)
O8—C91.453 (5)C16—H1610.960 (7)
C9—O81.453 (5)C16—H1620.960 (6)
C9—C101.505 (4)C17—C161.504 (5)
C9—H910.960 (6)C17—C181.505 (4)
C9—H920.960 (7)C17—H1710.961 (6)
C10—C91.505 (4)C17—H1720.961 (7)
C10—C111.505 (5)C18—C171.505 (4)
C10—H1010.960 (7)C18—H1810.960 (7)
C10—H1020.960 (6)C18—H1820.960 (6)
C11—C101.505 (5)C18—H1830.960 (7)
C11—C121.501 (4)
N2—C1—C491.4 (8)C11—C12—H121108.6 (4)
N2—C1—O5131.8 (5)C11—C12—H122108.6 (5)
C4—C1—O5136.1 (12)C13—C12—H121108.7 (5)
C1—N2—C396.6 (4)C13—C12—H122109.1 (9)
C1—N2—H21142.8 (6)H121—C12—H122108.6 (8)
C3—N2—H21120.1 (6)C12—C13—C14113.9 (2)
N2—C3—C484.7 (2)C12—C13—H131108.5 (9)
N2—C3—C6112.4 (3)C12—C13—H132108.6 (5)
N2—C3—H31112.8 (7)C14—C13—H131108.7 (5)
C4—C3—C6113.9 (3)C14—C13—H132108.8 (4)
C4—C3—H31113.4 (4)H131—C13—H132108.3 (7)
C6—C3—H31115.8 (6)C13—C14—C15114.8 (2)
C1—C4—C387.3 (7)C13—C14—H141108.4 (4)
C1—C4—H41113.5 (7)C13—C14—H142108.9 (4)
C1—C4—H42113.4 (9)C15—C14—H141107.8 (5)
C3—C4—H41113.4 (3)C15—C14—H142108.0 (7)
C3—C4—H42113.5 (5)H141—C14—H142108.6 (7)
H41—C4—H42113.3 (10)C14—C15—C16112.1 (2)
C3—C6—O7123.3 (4)C14—C15—H151109.0 (7)
C3—C6—O8112.9 (3)C14—C15—H152108.8 (5)
O7—C6—O8122.0 (4)C16—C15—H151109.0 (4)
C6—O8—C9117.0 (3)C16—C15—H152108.8 (4)
O8—C9—C10110.1 (3)H151—C15—H152109.2 (7)
O8—C9—H91109.2 (10)C15—C16—C17113.1 (2)
O8—C9—H92109.2 (5)C15—C16—H161108.9 (4)
C10—C9—H91109.4 (5)C15—C16—H162108.3 (5)
C10—C9—H92109.5 (4)C17—C16—H161109.3 (5)
H91—C9—H92109.4 (8)C17—C16—H162108.2 (9)
C9—C10—C11114.5 (2)H161—C16—H162108.8 (8)
C9—C10—H101108.0 (4)C16—C17—C18114.8 (3)
C9—C10—H102108.6 (5)C16—C17—H171108.3 (9)
C11—C10—H101108.6 (5)C16—C17—H172108.4 (5)
C11—C10—H102108.8 (9)C18—C17—H171108.2 (5)
H101—C10—H102108.2 (8)C18—C17—H172108.3 (4)
C10—C11—C12112.7 (2)H171—C17—H172108.7 (9)
C10—C11—H111109.1 (9)C17—C18—H181109.5 (3)
C10—C11—H112109.0 (5)C17—C18—H182109.8 (6)
C12—C11—H111108.6 (5)C17—C18—H183109.1 (5)
C12—C11—H112108.8 (4)H181—C18—H182109.3 (10)
H111—C11—H112108.6 (8)H181—C18—H183109.5 (8)
C11—C12—C13113.1 (2)H182—C18—H183109.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O5i0.959 (7)2.181 (12)2.909 (7)131.8 (8)
Symmetry code: (i) x+1, y1/2, z+1.
(L_10_phase_2) top
Crystal data top
Tetragonal, P43212c = 29.711 (6) Å
a = 8.3903 (4) ÅV = 2091.6 (5) Å3
Data collection top
2θmin = 1.509°, 2θmax = 32.069°, 2θstep = 0.005°
Refinement top
6312 data points
(KD5033_L12) (S)-4-dodecyloxycarbonyl-2-azetidinone top
Crystal data top
C16H29NO3F(000) = 312
Mr = 283.41Dx = 1.087 Mg m3
Monoclinic, P21Melting point: 339 K
Hall symbol: P 2ybµ = 0.07 mm1
a = 31.0841 (3) ÅT = 298 K
b = 5.35782 (4) ÅParticle morphology: needles
c = 5.21197 (5) Åwhite
β = 94.1094 (7)°cylinder, 40 × 1.0 mm
V = 865.79 (1) Å3Specimen preparation: Prepared at 298 K
Z = 2
Data collection top
High Resolution Diffractometer ID31, ESRF, Grenoble, France.Specimen mounting: borosilicate glass capillary
Radiation source: synchrotron, Beamline ID31Data collection mode: transmission
Double crystal Si 111 monochromatorScan method: continuous
Refinement top
Least-squares matrix: full222 parameters
Rp = 0.071140 restraints
Rwp = 0.1002 constraints
Rexp = 0.054H atoms treated by a mixture of independent and constrained refinement
R(F2) = 0.06302(Δ/σ)max = 0.04
Excluded region(s): The regions 1.400 to 1.435 and 4.270 to 4.280 correspond to peaks of an unidentified phaseBackground function: GSAS Background function number 1 with 15 terms. Shifted Chebyshev function of 1st kind 1: 148.915 2: -73.3412 3: 32.6652 4: -32.6057 5: 36.5341 6: -36.8704 7: 10.9484 8: 9.52083 9: -11.0118 10: -6.03155 11: 9.74578 12: 2.87723 13: -6.42629 14: 5.62938 15: 1.42565
Profile function: CW Profile function number 4 with 21 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 0.063 #4(GP) = 0.000 #5(LX) = 0.337 #6(ptec) = 1.41 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0030 #11(H/L) = 0.0020 #12(eta) = 0.0000 #13(S400 ) = 4.0E-04 #14(S040 ) = 1.1E-01 #15(S004 ) = 3.7E-01 #16(S220 ) = 1.8E-03 #17(S202 ) = -3.3E-03 #18(S022 ) = 3.5E-01 #19(S301 ) = 2.3E-03 #20(S103 ) = -6.8E-02 #21(S121 ) = 3.5E-02 Peak tails are ignored where the intensity is below 0.0001 times the peak Aniso. broadening axis 0.0 0.0 1.0, CW Profile function number 4 with 16 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 0.000 #4(GP) = 0.000 #5(LX) = 12.333 #6(ptec) = 0.00 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0030 #11(H/L) = 0.0060 #12(eta) = 0.0000 #13(S400 ) = 0.0E+00 #14(S004 ) = 0.0E+00 #15(S220 ) = 0.0E+00 #16(S202 ) = 0.0E+00 Peak tails are ignored where the intensity is below 0.0001 times the peak Aniso. broadening axis 0.0 0.0 1.0
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5386 (2)0.902 (3)1.3060 (11)0.1040 (17)*
N20.5390 (2)1.1445 (6)1.2433 (11)0.1040 (17)*
C30.57116 (14)1.2241 (7)1.4495 (10)0.1040 (17)*
C40.56713 (15)0.9532 (7)1.5451 (9)0.1040 (17)*
O50.5156 (3)0.7278 (8)1.2267 (14)0.1040 (17)*
C60.61425 (15)1.2889 (8)1.3528 (11)0.1040 (17)*
O70.6392 (2)1.4454 (9)1.4508 (13)0.1040 (17)*
O80.62641 (16)1.1322 (9)1.1758 (11)0.1040 (17)*
C90.66713 (14)1.1834 (7)1.0677 (9)0.1040 (17)*
C100.68292 (14)0.9464 (6)0.9508 (9)0.1115 (19)*
C110.72430 (14)0.9760 (6)0.8209 (9)0.1115 (19)*
C120.73895 (14)0.7421 (6)0.6929 (9)0.1115 (19)*
C130.77922 (14)0.7722 (6)0.5507 (9)0.1115 (19)*
C140.79609 (14)0.5331 (7)0.4436 (9)0.1115 (19)*
C150.83452 (14)0.5679 (6)0.2884 (9)0.1115 (19)*
C160.84778 (14)0.3336 (6)0.1565 (9)0.1115 (19)*
C170.89041 (14)0.3540 (6)0.0386 (9)0.1115 (19)*
C180.90348 (14)0.1177 (7)0.0907 (9)0.1115 (19)*
C190.94545 (14)0.1453 (7)0.2138 (9)0.1115 (19)*
C200.95802 (15)0.0860 (6)0.3538 (9)0.1115 (19)*
H310.5602 (4)1.3453 (10)1.5638 (17)0.120 (2)*
H410.5939 (2)0.8628 (10)1.552 (3)0.120 (2)*
H420.5524 (3)0.9401 (11)1.7004 (13)0.120 (2)*
H910.6877 (3)1.2399 (11)1.2013 (16)0.120 (2)*
H920.6630 (4)1.3096 (10)0.9375 (15)0.120 (2)*
H1010.6872 (4)0.8239 (10)1.0847 (15)0.129 (2)*
H1020.6610 (3)0.8870 (11)0.8265 (17)0.129 (2)*
H1110.7465 (3)1.0282 (11)0.9472 (17)0.129 (2)*
H1120.7202 (4)1.1043 (10)0.6928 (15)0.129 (2)*
H1210.7442 (4)0.6164 (10)0.8228 (15)0.129 (2)*
H1220.7160 (3)0.6858 (11)0.5736 (17)0.129 (2)*
H1310.8014 (3)0.8427 (11)0.6662 (18)0.129 (2)*
H1320.7732 (4)0.8865 (10)0.4109 (14)0.129 (2)*
H1410.8039 (4)0.4223 (10)0.5839 (14)0.129 (2)*
H1420.7735 (3)0.4568 (11)0.3352 (19)0.129 (2)*
H1510.8583 (3)0.6256 (11)0.4001 (18)0.129 (2)*
H1520.8277 (4)0.6929 (10)0.1600 (15)0.129 (2)*
H1610.8495 (4)0.2001 (9)0.2796 (15)0.129 (2)*
H1620.8260 (3)0.2935 (11)0.0233 (16)0.129 (2)*
H1710.9123 (3)0.3963 (11)0.1707 (16)0.129 (2)*
H1720.8886 (4)0.4858 (9)0.0865 (15)0.129 (2)*
H1810.9064 (4)0.0135 (9)0.0349 (15)0.129 (2)*
H1820.8814 (3)0.0721 (11)0.2203 (17)0.129 (2)*
H1910.9677 (3)0.1835 (11)0.0821 (16)0.129 (2)*
H1920.9431 (4)0.2817 (9)0.3336 (16)0.129 (2)*
H2010.9750 (3)0.0403 (11)0.4933 (15)0.129 (2)*
H2020.9746 (3)0.1938 (10)0.2371 (17)0.129 (2)*
H2030.9325 (2)0.1718 (10)0.420 (2)0.129 (2)*
H210.5245 (5)1.2668 (10)1.134 (2)0.120 (2)*
Geometric parameters (Å, º) top
C1—N21.342 (18)C12—H1210.960 (6)
C1—C41.504 (6)C12—H1220.960 (6)
C1—O51.227 (14)C13—C121.509 (5)
N2—C11.342 (18)C13—C141.506 (4)
N2—C31.477 (5)C13—H1310.960 (6)
N2—H210.960 (7)C13—H1320.960 (6)
C3—N21.477 (5)C14—C131.506 (4)
C3—C41.543 (4)C14—C151.502 (5)
C3—C61.505 (5)C14—H1410.960 (6)
C3—H310.960 (6)C14—H1420.960 (6)
C4—C11.504 (6)C15—C141.502 (5)
C4—C31.543 (4)C15—C161.503 (4)
C4—H410.960 (6)C15—H1510.960 (6)
C4—H420.960 (6)C15—H1520.960 (6)
O5—C11.227 (14)C16—C151.503 (4)
C6—C31.505 (5)C16—C171.504 (5)
C6—O71.229 (5)C16—H1610.960 (6)
C6—O81.322 (5)C16—H1620.960 (6)
O7—C61.229 (5)C17—C161.504 (5)
O8—C61.322 (5)C17—C181.504 (4)
O8—C91.448 (5)C17—H1710.960 (6)
C9—O81.448 (5)C17—H1720.960 (6)
C9—C101.506 (4)C18—C171.504 (4)
C9—H910.960 (6)C18—C191.502 (5)
C9—H920.960 (6)C18—H1810.960 (6)
C10—C91.506 (4)C18—H1820.960 (6)
C10—C111.505 (5)C19—C181.502 (5)
C10—H1010.960 (6)C19—C201.504 (4)
C10—H1020.960 (6)C19—H1910.960 (6)
C11—C101.505 (5)C19—H1920.961 (6)
C11—C121.505 (4)C20—C191.504 (4)
C11—H1110.960 (6)C20—H2010.961 (7)
C11—H1120.960 (6)C20—H2020.961 (6)
C12—C111.505 (4)C20—H2030.960 (6)
C12—C131.509 (5)
N2—C1—C490.4 (9)C12—C13—H131108.6 (7)
N2—C1—O5132.0 (7)C12—C13—H132108.6 (8)
C4—C1—O5135.5 (11)C14—C13—H131108.3 (5)
C1—N2—C397.0 (4)C14—C13—H132108.4 (6)
C1—N2—H21142.6 (7)H131—C13—H132108.5 (7)
C3—N2—H21120.0 (6)C13—C14—C15113.9 (3)
N2—C3—C484.1 (3)C13—C14—H141108.6 (6)
N2—C3—C6113.3 (5)C13—C14—H142108.8 (5)
N2—C3—H31113.2 (8)C15—C14—H141108.6 (8)
C4—C3—C6114.8 (4)C15—C14—H142108.1 (7)
C4—C3—H31113.3 (6)H141—C14—H142108.7 (7)
C6—C3—H31114.6 (7)C14—C15—C16113.4 (3)
C1—C4—C387.8 (7)C14—C15—H151108.8 (7)
C1—C4—H41113.3 (8)C14—C15—H152108.6 (8)
C1—C4—H42113.3 (7)C16—C15—H151108.8 (5)
C3—C4—H41113.4 (5)C16—C15—H152108.5 (6)
C3—C4—H42113.3 (5)H151—C15—H152108.6 (7)
H41—C4—H42113.3 (8)C15—C16—C17113.9 (3)
C3—C6—O7124.7 (5)C15—C16—H161108.7 (6)
C3—C6—O8113.1 (4)C15—C16—H162108.4 (5)
O7—C6—O8121.3 (5)C17—C16—H161108.6 (8)
C6—O8—C9116.9 (4)C17—C16—H162108.6 (7)
O8—C9—C10108.5 (3)H161—C16—H162108.6 (8)
O8—C9—H91109.4 (7)C16—C17—C18113.4 (3)
O8—C9—H92109.4 (8)C16—C17—H171108.9 (7)
C10—C9—H91109.9 (5)C16—C17—H172108.6 (8)
C10—C9—H92109.8 (6)C18—C17—H171108.6 (5)
H91—C9—H92109.9 (7)C18—C17—H172108.7 (6)
C9—C10—C11114.0 (3)H171—C17—H172108.5 (8)
C9—C10—H101108.3 (6)C17—C18—C19112.3 (3)
C9—C10—H102108.4 (5)C17—C18—H181109.0 (6)
C11—C10—H101108.8 (8)C17—C18—H182109.1 (5)
C11—C10—H102108.7 (7)C19—C18—H181108.7 (8)
H101—C10—H102108.5 (7)C19—C18—H182108.9 (7)
C10—C11—C12114.0 (3)H181—C18—H182108.7 (7)
C10—C11—H111108.5 (7)C18—C19—C20113.0 (3)
C10—C11—H112108.3 (8)C18—C19—H191108.6 (7)
C12—C11—H111108.7 (5)C18—C19—H192108.9 (8)
C12—C11—H112108.5 (6)C20—C19—H191108.9 (5)
H111—C11—H112108.7 (7)C20—C19—H192108.8 (6)
C11—C12—C13114.6 (3)H191—C19—H192108.6 (8)
C11—C12—H121108.3 (6)C19—C20—H201109.5 (5)
C11—C12—H122108.3 (5)C19—C20—H202109.5 (6)
C13—C12—H121108.3 (8)C19—C20—H203109.4 (6)
C13—C12—H122108.6 (7)H201—C20—H202109.5 (8)
H121—C12—H122108.6 (7)H201—C20—H203109.5 (8)
C12—C13—C14114.5 (3)H202—C20—H203109.3 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O5i0.959 (11)2.536 (7)3.209 (6)127.3 (8)
N2—H21···O5ii0.959 (11)2.190 (14)2.913 (10)131.2 (7)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+2.
(L_12_phase_2) top
Crystal data top
Tetragonal, P43212c = 29.653 (19) Å
a = 8.414 (2) ÅV = 2099.5 (17) Å3
Data collection top
2θmin = 1.009°, 2θmax = 32.069°, 2θstep = 0.005°
Refinement top
6312 data points
(KD5033_L_16) (S)-4-hexadecyloxycarbonyl-2-azetidinone top
Crystal data top
C20H37NO3F(000) = 376
Mr = 339.52Dx = 1.067 Mg m3
Monoclinic, P21Melting point: 349 K
Hall symbol: P 2ybµ = 0.07 mm1
a = 37.1586 (3) ÅT = 298 K
b = 5.35911 (5) ÅParticle morphology: needles
c = 5.30974 (5) Åwhite
β = 92.1693 (6)°cylinder, 40 × 1.0 mm
V = 1056.61 (2) Å3Specimen preparation: Prepared at 298 K
Z = 2
Data collection top
High Resolution Diffractometer ID31, ESRF, Grenoble, France.Data collection mode: transmission
Radiation source: synchrotron, Beamline ID31Scan method: continuous
Double crystal Si 111 monochromator2θmin = 0.509°, 2θmax = 32.069°, 2θstep = 0.005°
Specimen mounting: borosilicate glass capillary
Refinement top
Least-squares matrix: fullProfile function: CW Profile function number 4 with 21 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 0.110 #4(GP) = 0.000 #5(LX) = 0.269 #6(ptec) = 1.68 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0030 #11(H/L) = 0.0021 #12(eta) = 0.0000 #13(S400 ) = 4.3E-04 #14(S040 ) = 2.5E-01 #15(S004 ) = 8.7E-01 #16(S220 ) = -3.8E-04 #17(S202 ) = -9.0E-03 #18(S022 ) = 6.2E-01 #19(S301 ) = -2.6E-03 #20(S103 ) = 1.3E-01 #21(S121 ) = -3.4E-02 Peak tails are ignored where the intensity is below 0.0001 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rp = 0.078256 parameters
Rwp = 0.107185 restraints
Rexp = 0.0492 constraints
R(F2) = 0.06998H atoms treated by a mixture of independent and constrained refinement
6312 data points(Δ/σ)max = 0.03
Excluded region(s): The region 1.725 to 1.765 correspond to peak of an unidentified phaseBackground function: GSAS Background function number 1 with 16 terms. Shifted Chebyshev function of 1st kind 1: 174.731 2: -69.0201 3: 29.5791 4: -27.7684 5: 27.0858 6: -27.6400 7: -5.19894 8: 24.4862 9: -20.0027 10: -7.46537 11: 9.13741 12: 7.24856 13: -7.66897 14: 3.46197 15: 10.3473 16: -4.77013
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4684 (3)0.236 (12)1.7763 (19)0.1073 (16)*
C40.4441 (2)0.1744 (13)1.9974 (17)0.1073 (16)*
C30.4441 (2)0.0823 (13)1.876 (2)0.1073 (16)*
N20.4670 (3)0.0024 (13)1.6950 (17)0.1073 (16)*
O50.4839 (3)0.4177 (15)1.7047 (15)0.1073 (16)*
C60.4085 (2)0.1580 (15)1.759 (2)0.1073 (16)*
O70.3877 (2)0.3088 (15)1.8531 (17)0.1073 (16)*
O80.3962 (2)0.0020 (15)1.5877 (15)0.1073 (16)*
C90.3628 (2)0.0581 (14)1.4481 (16)0.1073 (16)*
C100.3484 (2)0.1795 (13)1.3235 (16)0.0986 (12)*
C110.3146 (2)0.1503 (13)1.1528 (16)0.0986 (12)*
C120.3006 (2)0.3937 (14)1.0461 (15)0.0986 (12)*
C130.2722 (2)0.3572 (13)0.8375 (16)0.0986 (12)*
C140.2569 (2)0.5939 (14)0.7175 (16)0.0986 (12)*
C150.2216 (2)0.5494 (14)0.5550 (16)0.0986 (12)*
C160.2092 (2)0.7777 (13)0.4102 (16)0.0986 (12)*
C170.1806 (2)0.7287 (13)0.2059 (16)0.0986 (12)*
C180.1665 (2)0.9652 (14)0.0907 (16)0.0986 (12)*
C190.1353 (2)0.9257 (14)0.0886 (17)0.0986 (12)*
C200.1241 (2)1.1620 (13)0.2230 (16)0.0986 (12)*
C210.0886 (2)1.1365 (14)0.3819 (16)0.0986 (12)*
C220.0755 (2)1.3743 (14)0.5033 (16)0.0986 (12)*
C230.0479 (2)1.3383 (13)0.7034 (16)0.0986 (12)*
C240.0375 (2)1.5813 (14)0.8330 (16)0.0986 (12)*
H410.4224 (4)0.272 (2)1.994 (4)0.1237 (19)*
H420.4567 (5)0.1790 (19)2.159 (4)0.1237 (19)*
H310.4545 (5)0.206 (2)1.985 (5)0.1237 (19)*
H910.3456 (6)0.124 (2)1.560 (4)0.1237 (19)*
H920.3678 (6)0.179 (2)1.321 (4)0.1237 (19)*
H1010.3432 (6)0.297 (2)1.455 (4)0.1134 (15)*
H1020.3673 (6)0.249 (2)1.224 (4)0.1134 (15)*
H1110.2961 (6)0.075 (2)1.249 (4)0.1134 (15)*
H1120.3197 (6)0.042 (2)1.016 (4)0.1134 (15)*
H1210.2904 (6)0.489 (2)1.180 (4)0.1134 (15)*
H1220.3203 (6)0.485 (2)0.980 (4)0.1134 (15)*
H1310.2527 (6)0.265 (2)0.905 (4)0.1134 (15)*
H1320.2825 (6)0.259 (2)0.708 (4)0.1134 (15)*
H1410.2521 (6)0.711 (2)0.848 (4)0.1134 (15)*
H1420.2747 (6)0.664 (2)0.611 (4)0.1134 (15)*
H1510.2027 (6)0.497 (2)0.663 (4)0.1134 (15)*
H1520.2257 (6)0.419 (2)0.436 (4)0.1134 (15)*
H1610.1997 (6)0.896 (2)0.527 (4)0.1134 (15)*
H1620.2295 (6)0.851 (2)0.334 (4)0.1134 (15)*
H1710.1610 (6)0.641 (2)0.279 (4)0.1134 (15)*
H1720.1904 (6)0.626 (2)0.078 (4)0.1134 (15)*
H1810.1594 (6)1.074 (2)0.223 (4)0.1134 (15)*
H1820.1852 (6)1.044 (2)0.002 (4)0.1134 (15)*
H1910.1153 (6)0.864 (2)0.003 (4)0.1134 (15)*
H1920.1418 (6)0.802 (2)0.209 (5)0.1134 (15)*
H2010.1214 (6)1.290 (2)0.101 (4)0.1134 (15)*
H2020.1429 (6)1.210 (2)0.331 (4)0.1134 (15)*
H2110.0703 (6)1.077 (2)0.274 (4)0.1134 (15)*
H2120.0920 (6)1.015 (2)0.513 (4)0.1134 (15)*
H2210.0656 (6)1.478 (2)0.376 (4)0.1134 (15)*
H2220.0955 (6)1.459 (2)0.574 (4)0.1134 (15)*
H2310.0271 (6)1.268 (2)0.631 (4)0.1134 (15)*
H2320.0568 (6)1.224 (2)0.826 (4)0.1134 (15)*
H2410.0120 (6)1.608 (2)0.820 (4)0.1134 (15)*
H2420.0505 (6)1.717 (2)0.753 (4)0.1134 (15)*
H2430.0434 (6)1.573 (2)1.008 (4)0.1134 (15)*
H210.4743 (8)0.115 (2)1.567 (5)0.1237 (19)*
Geometric parameters (Å, º) top
C1—C41.55 (2)C14—H1410.956 (19)
C1—N21.35 (6)C14—H1420.96 (2)
C1—O51.20 (6)C15—C141.560 (11)
C4—C11.55 (2)C15—C161.508 (11)
C4—C31.519 (11)C15—H1510.96 (2)
C4—H410.960 (14)C15—H1520.959 (18)
C4—H420.97 (2)C16—C151.508 (11)
C3—C41.519 (11)C16—C171.513 (11)
C3—C61.496 (12)C16—H1610.964 (19)
C3—H310.95 (2)C16—H1620.95 (2)
N2—C11.35 (6)C17—C161.513 (11)
N2—C31.377 (13)C17—C181.493 (11)
N2—H210.96 (2)C17—H1710.96 (2)
O5—C11.20 (6)C17—H1720.96 (2)
C6—C31.496 (12)C18—C171.493 (11)
C6—O71.238 (12)C18—C191.489 (12)
C6—O81.317 (12)C18—H1810.96 (2)
O7—C61.238 (12)C18—H1820.95 (2)
O8—C61.317 (12)C19—C181.489 (12)
O8—C91.457 (11)C19—C201.504 (11)
C9—O81.457 (11)C19—H1910.96 (2)
C9—C101.523 (11)C19—H1920.96 (2)
C9—H910.96 (2)C20—C191.504 (11)
C9—H920.960 (19)C20—C211.543 (11)
C10—C91.523 (11)C20—H2010.954 (18)
C10—C111.531 (11)C20—H2020.96 (2)
C10—H1010.965 (19)C21—C201.543 (11)
C10—H1020.97 (2)C21—C221.501 (11)
C11—C101.531 (11)C21—H2110.96 (2)
C11—C121.506 (10)C21—H2120.964 (19)
C11—H1110.96 (2)C22—C211.501 (11)
C11—H1120.96 (2)C22—C231.462 (11)
C12—C111.506 (10)C22—H2210.96 (2)
C12—C131.514 (11)C22—H2220.96 (2)
C12—H1210.97 (2)C23—C221.462 (11)
C12—H1220.96 (2)C23—C241.516 (11)
C13—C121.514 (11)C23—H2310.95 (2)
C13—C141.520 (11)C23—H2320.964 (19)
C13—H1310.96 (2)C24—C231.516 (11)
C13—H1320.96 (2)C24—H2410.96 (2)
C14—C131.520 (11)C24—H2420.965 (18)
C14—C151.560 (11)C24—H2430.97 (2)
C4—C1—N291 (3)C14—C15—H151109.2 (14)
C4—C1—O5136 (4)C14—C15—H152108.7 (14)
N2—C1—O5132.9 (15)C16—C15—H151109.0 (12)
C1—C4—C382 (2)C16—C15—H152108.2 (13)
C1—C4—H41113 (2)H151—C15—H152108.6 (15)
C1—C4—H42113.1 (14)C15—C16—C17114.7 (6)
C3—C4—H41120.1 (11)C15—C16—H161108.4 (13)
C3—C4—H42113.1 (9)C15—C16—H162108.4 (12)
H41—C4—H42112.4 (17)C17—C16—H161108.3 (14)
C4—C3—N291.4 (6)C17—C16—H162108.3 (14)
C4—C3—C6114.1 (7)H161—C16—H162108.6 (15)
C4—C3—H31112.3 (15)C16—C17—C18111.8 (6)
N2—C3—C6110.7 (9)C16—C17—H171108.6 (14)
N2—C3—H31113.1 (14)C16—C17—H172109.5 (14)
C6—C3—H31113.4 (12)C18—C17—H171108.8 (12)
C1—N2—C395.1 (10)C18—C17—H172109.4 (12)
C1—N2—H21144.8 (17)H171—C17—H172108.7 (15)
C3—N2—H21120.0 (15)C17—C18—C19113.2 (6)
C3—C6—O7124.3 (9)C17—C18—H181108.8 (12)
C3—C6—O8112.8 (7)C17—C18—H182109.0 (12)
O7—C6—O8120.0 (9)C19—C18—H181108.9 (14)
C6—O8—C9118.2 (7)C19—C18—H182108.4 (14)
O8—C9—C10108.4 (6)H181—C18—H182108.5 (16)
O8—C9—H91110.0 (14)C18—C19—C20112.2 (6)
O8—C9—H92109.0 (14)C18—C19—H191108.9 (15)
C10—C9—H91110.3 (12)C18—C19—H192108.3 (15)
C10—C9—H92109.4 (13)C20—C19—H191108.9 (12)
H91—C9—H92109.8 (15)C20—C19—H192109.8 (15)
C9—C10—C11116.1 (6)H191—C19—H192108.7 (16)
C9—C10—H101107.9 (12)C19—C20—C21113.5 (6)
C9—C10—H102108.0 (12)C19—C20—H201108.5 (13)
C11—C10—H101108.2 (14)C19—C20—H202108.3 (11)
C11—C10—H102108.3 (14)C21—C20—H201109.1 (14)
H101—C10—H102108.1 (16)C21—C20—H202108.9 (14)
C10—C11—C12113.5 (6)H201—C20—H202108.4 (16)
C10—C11—H111108.5 (14)C20—C21—C22114.5 (6)
C10—C11—H112109.2 (14)C20—C21—H211108.3 (14)
C12—C11—H111108.6 (12)C20—C21—H212108.8 (14)
C12—C11—H112108.5 (12)C22—C21—H211108.2 (11)
H111—C11—H112108.5 (16)C22—C21—H212108.1 (12)
C11—C12—C13112.6 (6)H211—C21—H212108.8 (16)
C11—C12—H121108.6 (12)C21—C22—C23114.0 (6)
C11—C12—H122108.9 (12)C21—C22—H221108.5 (12)
C13—C12—H121109.0 (14)C21—C22—H222108.9 (12)
C13—C12—H122108.6 (14)C23—C22—H221108.1 (14)
H121—C12—H122109.1 (15)C23—C22—H222108.2 (14)
C12—C13—C14116.0 (6)H221—C22—H222109.0 (15)
C12—C13—H131108.1 (14)C22—C23—C24112.1 (6)
C12—C13—H132108.0 (14)C22—C23—H231108.6 (14)
C14—C13—H131108.1 (12)C22—C23—H232109.1 (14)
C14—C13—H132108.1 (12)C24—C23—H231108.9 (12)
H131—C13—H132108.4 (15)C24—C23—H232109.2 (12)
C13—C14—C15113.4 (6)H231—C23—H232108.9 (15)
C13—C14—H141108.8 (13)C23—C24—H241109.3 (11)
C13—C14—H142108.4 (12)C23—C24—H242109.5 (13)
C15—C14—H141109.0 (14)C23—C24—H243109.6 (10)
C15—C14—H142108.5 (14)H241—C24—H242109.5 (16)
H141—C14—H142108.5 (15)H241—C24—H243109.7 (19)
C14—C15—C16113.1 (6)H242—C24—H243109.3 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O5i0.96 (2)2.17 (3)2.883 (14)130.7 (17)
Symmetry code: (i) x+1, y1/2, z+3.
 

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