research papers
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—HO.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109036386/kd5033sup1.cif |
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_L_10) (S)-4-decyloxycarbonyl-2-azetidinone top
Crystal data top
C14H25NO3 | F(000) = 280 |
Mr = 255.36 | Dx = 1.102 Mg m−3 |
Monoclinic, P21 | Melting point: 324 K |
Hall symbol: P 2yb | µ = 0.08 mm−1 |
a = 27.82406 (16) Å | T = 298 K |
b = 5.35267 (4) Å | Particle morphology: needles |
c = 5.16992 (3) Å | white |
β = 92.0469 (4)° | cylinder, 40 × 1.0 mm |
V = 769.48 (1) Å3 | Specimen 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 ID31 | Data collection mode: transmission |
Double crystal Si 111 monochromator | Scan method: continuous |
Refinement top
Least-squares matrix: full | 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) = 0.075 #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 = 0.075 | 193 parameters |
Rwp = 0.104 | 122 restraints |
Rexp = 0.060 | (Δ/σ)max = 0.04 |
R(F2) = 0.08634 | Background 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
x | y | z | Uiso*/Ueq | ||
C1 | 0.45961 (16) | 0.636 (3) | 0.7976 (8) | 0.1126 (19)* | |
N2 | 0.45533 (17) | 0.3998 (4) | 0.7128 (7) | 0.1126 (19)* | |
C3 | 0.42000 (12) | 0.3186 (5) | 0.9022 (7) | 0.1126 (19)* | |
C4 | 0.42245 (12) | 0.5923 (5) | 0.9970 (6) | 0.1126 (19)* | |
O5 | 0.48089 (18) | 0.8169 (5) | 0.7126 (10) | 0.1126 (19)* | |
C6 | 0.37244 (13) | 0.2480 (5) | 0.7751 (8) | 0.1243 (11)* | |
O7 | 0.34511 (18) | 0.0931 (6) | 0.8658 (12) | 0.1243 (11)* | |
O8 | 0.35795 (14) | 0.4078 (6) | 0.5927 (8) | 0.1243 (11)* | |
C9 | 0.31034 (12) | 0.3688 (5) | 0.4752 (7) | 0.1243 (11)* | |
C10 | 0.29463 (12) | 0.5970 (5) | 0.3247 (7) | 0.1243 (11)* | |
C11 | 0.24668 (12) | 0.5716 (5) | 0.1832 (7) | 0.1243 (11)* | |
C12 | 0.23224 (12) | 0.8039 (5) | 0.0377 (7) | 0.1243 (11)* | |
C13 | 0.18574 (12) | 0.7758 (5) | −0.1161 (7) | 0.1243 (11)* | |
C14 | 0.16767 (12) | 1.0148 (5) | −0.2381 (7) | 0.1243 (11)* | |
C15 | 0.12452 (12) | 0.9859 (5) | −0.4178 (7) | 0.1243 (11)* | |
C16 | 0.10654 (12) | 1.2327 (5) | −0.5192 (7) | 0.1243 (11)* | |
C17 | 0.05908 (12) | 1.2135 (5) | −0.6664 (6) | 0.1243 (11)* | |
C18 | 0.04716 (12) | 1.4325 (5) | −0.8396 (7) | 0.1243 (11)* | |
H31 | 0.4332 (4) | 0.2013 (6) | 1.0260 (13) | 0.156 (3)* | |
H41 | 0.4348 (4) | 0.6088 (7) | 1.1719 (9) | 0.156 (3)* | |
H42 | 0.39320 (19) | 0.6838 (6) | 0.964 (3) | 0.156 (3)* | |
H91 | 0.3112 (6) | 0.2278 (6) | 0.3607 (13) | 0.1442 (13)* | |
H92 | 0.2880 (2) | 0.3365 (7) | 0.6086 (11) | 0.1442 (13)* | |
H101 | 0.3186 (2) | 0.6326 (7) | 0.2009 (12) | 0.1442 (13)* | |
H102 | 0.2932 (6) | 0.7357 (6) | 0.4420 (13) | 0.1442 (13)* | |
H111 | 0.2481 (6) | 0.4357 (6) | 0.0626 (13) | 0.1442 (13)* | |
H112 | 0.2226 (2) | 0.5344 (7) | 0.3058 (12) | 0.1442 (13)* | |
H121 | 0.2572 (2) | 0.8454 (7) | −0.0785 (13) | 0.1442 (13)* | |
H122 | 0.2292 (5) | 0.9380 (6) | 0.1593 (12) | 0.1442 (13)* | |
H131 | 0.1903 (5) | 0.6550 (6) | −0.2502 (11) | 0.1442 (13)* | |
H132 | 0.1618 (2) | 0.7132 (7) | −0.0038 (13) | 0.1442 (13)* | |
H141 | 0.1931 (2) | 1.0863 (6) | −0.3348 (15) | 0.1442 (13)* | |
H142 | 0.1595 (4) | 1.1294 (6) | −0.1038 (11) | 0.1442 (13)* | |
H151 | 0.1329 (4) | 0.8826 (6) | −0.5610 (11) | 0.1442 (13)* | |
H152 | 0.0993 (2) | 0.9066 (6) | −0.3260 (15) | 0.1442 (13)* | |
H161 | 0.1301 (2) | 1.3025 (6) | −0.6297 (13) | 0.1442 (13)* | |
H162 | 0.1026 (5) | 1.3427 (6) | −0.3748 (11) | 0.1442 (13)* | |
H171 | 0.0595 (6) | 1.0657 (6) | −0.7716 (14) | 0.1442 (13)* | |
H172 | 0.0341 (2) | 1.1970 (7) | −0.5440 (12) | 0.1442 (13)* | |
H181 | 0.0338 (4) | 1.3734 (7) | −1.0022 (10) | 0.1442 (13)* | |
H182 | 0.07579 (19) | 1.5269 (6) | −0.869 (3) | 0.1442 (13)* | |
H183 | 0.0241 (2) | 1.5368 (6) | −0.7577 (17) | 0.1442 (13)* | |
H21 | 0.4638 (5) | 0.2906 (6) | 0.5745 (11) | 0.156 (3)* |
Geometric parameters (Å, º) top
C1—N2 | 1.340 (18) | C11—H111 | 0.960 (6) |
C1—C4 | 1.504 (6) | C11—H112 | 0.960 (7) |
C1—O5 | 1.226 (15) | C12—C11 | 1.501 (4) |
N2—C1 | 1.340 (18) | C12—C13 | 1.502 (5) |
N2—C3 | 1.477 (5) | C12—H121 | 0.959 (7) |
N2—H21 | 0.960 (7) | C12—H122 | 0.960 (6) |
C3—N2 | 1.477 (5) | C13—C12 | 1.502 (5) |
C3—C4 | 1.546 (4) | C13—C14 | 1.504 (4) |
C3—C6 | 1.504 (5) | C13—H131 | 0.960 (6) |
C3—H31 | 0.960 (7) | C13—H132 | 0.960 (7) |
C4—C1 | 1.504 (6) | C14—C13 | 1.504 (4) |
C4—C3 | 1.546 (4) | C14—C15 | 1.500 (5) |
C4—H41 | 0.960 (6) | C14—H141 | 0.960 (7) |
C4—H42 | 0.960 (6) | C14—H142 | 0.959 (6) |
O5—C1 | 1.226 (15) | C15—C14 | 1.500 (5) |
C6—C3 | 1.504 (5) | C15—C16 | 1.500 (4) |
C6—O7 | 1.229 (5) | C15—H151 | 0.960 (6) |
C6—O8 | 1.325 (5) | C15—H152 | 0.960 (7) |
O7—C6 | 1.229 (5) | C16—C15 | 1.500 (4) |
O8—C6 | 1.325 (5) | C16—C17 | 1.504 (5) |
O8—C9 | 1.453 (5) | C16—H161 | 0.960 (7) |
C9—O8 | 1.453 (5) | C16—H162 | 0.960 (6) |
C9—C10 | 1.505 (4) | C17—C16 | 1.504 (5) |
C9—H91 | 0.960 (6) | C17—C18 | 1.505 (4) |
C9—H92 | 0.960 (7) | C17—H171 | 0.961 (6) |
C10—C9 | 1.505 (4) | C17—H172 | 0.961 (7) |
C10—C11 | 1.505 (5) | C18—C17 | 1.505 (4) |
C10—H101 | 0.960 (7) | C18—H181 | 0.960 (7) |
C10—H102 | 0.960 (6) | C18—H182 | 0.960 (6) |
C11—C10 | 1.505 (5) | C18—H183 | 0.960 (7) |
C11—C12 | 1.501 (4) | ||
N2—C1—C4 | 91.4 (8) | C11—C12—H121 | 108.6 (4) |
N2—C1—O5 | 131.8 (5) | C11—C12—H122 | 108.6 (5) |
C4—C1—O5 | 136.1 (12) | C13—C12—H121 | 108.7 (5) |
C1—N2—C3 | 96.6 (4) | C13—C12—H122 | 109.1 (9) |
C1—N2—H21 | 142.8 (6) | H121—C12—H122 | 108.6 (8) |
C3—N2—H21 | 120.1 (6) | C12—C13—C14 | 113.9 (2) |
N2—C3—C4 | 84.7 (2) | C12—C13—H131 | 108.5 (9) |
N2—C3—C6 | 112.4 (3) | C12—C13—H132 | 108.6 (5) |
N2—C3—H31 | 112.8 (7) | C14—C13—H131 | 108.7 (5) |
C4—C3—C6 | 113.9 (3) | C14—C13—H132 | 108.8 (4) |
C4—C3—H31 | 113.4 (4) | H131—C13—H132 | 108.3 (7) |
C6—C3—H31 | 115.8 (6) | C13—C14—C15 | 114.8 (2) |
C1—C4—C3 | 87.3 (7) | C13—C14—H141 | 108.4 (4) |
C1—C4—H41 | 113.5 (7) | C13—C14—H142 | 108.9 (4) |
C1—C4—H42 | 113.4 (9) | C15—C14—H141 | 107.8 (5) |
C3—C4—H41 | 113.4 (3) | C15—C14—H142 | 108.0 (7) |
C3—C4—H42 | 113.5 (5) | H141—C14—H142 | 108.6 (7) |
H41—C4—H42 | 113.3 (10) | C14—C15—C16 | 112.1 (2) |
C3—C6—O7 | 123.3 (4) | C14—C15—H151 | 109.0 (7) |
C3—C6—O8 | 112.9 (3) | C14—C15—H152 | 108.8 (5) |
O7—C6—O8 | 122.0 (4) | C16—C15—H151 | 109.0 (4) |
C6—O8—C9 | 117.0 (3) | C16—C15—H152 | 108.8 (4) |
O8—C9—C10 | 110.1 (3) | H151—C15—H152 | 109.2 (7) |
O8—C9—H91 | 109.2 (10) | C15—C16—C17 | 113.1 (2) |
O8—C9—H92 | 109.2 (5) | C15—C16—H161 | 108.9 (4) |
C10—C9—H91 | 109.4 (5) | C15—C16—H162 | 108.3 (5) |
C10—C9—H92 | 109.5 (4) | C17—C16—H161 | 109.3 (5) |
H91—C9—H92 | 109.4 (8) | C17—C16—H162 | 108.2 (9) |
C9—C10—C11 | 114.5 (2) | H161—C16—H162 | 108.8 (8) |
C9—C10—H101 | 108.0 (4) | C16—C17—C18 | 114.8 (3) |
C9—C10—H102 | 108.6 (5) | C16—C17—H171 | 108.3 (9) |
C11—C10—H101 | 108.6 (5) | C16—C17—H172 | 108.4 (5) |
C11—C10—H102 | 108.8 (9) | C18—C17—H171 | 108.2 (5) |
H101—C10—H102 | 108.2 (8) | C18—C17—H172 | 108.3 (4) |
C10—C11—C12 | 112.7 (2) | H171—C17—H172 | 108.7 (9) |
C10—C11—H111 | 109.1 (9) | C17—C18—H181 | 109.5 (3) |
C10—C11—H112 | 109.0 (5) | C17—C18—H182 | 109.8 (6) |
C12—C11—H111 | 108.6 (5) | C17—C18—H183 | 109.1 (5) |
C12—C11—H112 | 108.8 (4) | H181—C18—H182 | 109.3 (10) |
H111—C11—H112 | 108.6 (8) | H181—C18—H183 | 109.5 (8) |
C11—C12—C13 | 113.1 (2) | H182—C18—H183 | 109.6 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O5i | 0.959 (7) | 2.181 (12) | 2.909 (7) | 131.8 (8) |
Symmetry code: (i) −x+1, y−1/2, −z+1. |
(L_10_phase_2) top
(KD5033_L12) (S)-4-dodecyloxycarbonyl-2-azetidinone top
Crystal data top
C16H29NO3 | F(000) = 312 |
Mr = 283.41 | Dx = 1.087 Mg m−3 |
Monoclinic, P21 | Melting point: 339 K |
Hall symbol: P 2yb | µ = 0.07 mm−1 |
a = 31.0841 (3) Å | T = 298 K |
b = 5.35782 (4) Å | Particle morphology: needles |
c = 5.21197 (5) Å | white |
β = 94.1094 (7)° | cylinder, 40 × 1.0 mm |
V = 865.79 (1) Å3 | Specimen 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 ID31 | Data collection mode: transmission |
Double crystal Si 111 monochromator | Scan method: continuous |
Refinement top
Least-squares matrix: full | 222 parameters |
Rp = 0.071 | 140 restraints |
Rwp = 0.100 | 2 constraints |
Rexp = 0.054 | H 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 phase | Background 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
x | y | z | Uiso*/Ueq | ||
C1 | 0.5386 (2) | 0.902 (3) | 1.3060 (11) | 0.1040 (17)* | |
N2 | 0.5390 (2) | 1.1445 (6) | 1.2433 (11) | 0.1040 (17)* | |
C3 | 0.57116 (14) | 1.2241 (7) | 1.4495 (10) | 0.1040 (17)* | |
C4 | 0.56713 (15) | 0.9532 (7) | 1.5451 (9) | 0.1040 (17)* | |
O5 | 0.5156 (3) | 0.7278 (8) | 1.2267 (14) | 0.1040 (17)* | |
C6 | 0.61425 (15) | 1.2889 (8) | 1.3528 (11) | 0.1040 (17)* | |
O7 | 0.6392 (2) | 1.4454 (9) | 1.4508 (13) | 0.1040 (17)* | |
O8 | 0.62641 (16) | 1.1322 (9) | 1.1758 (11) | 0.1040 (17)* | |
C9 | 0.66713 (14) | 1.1834 (7) | 1.0677 (9) | 0.1040 (17)* | |
C10 | 0.68292 (14) | 0.9464 (6) | 0.9508 (9) | 0.1115 (19)* | |
C11 | 0.72430 (14) | 0.9760 (6) | 0.8209 (9) | 0.1115 (19)* | |
C12 | 0.73895 (14) | 0.7421 (6) | 0.6929 (9) | 0.1115 (19)* | |
C13 | 0.77922 (14) | 0.7722 (6) | 0.5507 (9) | 0.1115 (19)* | |
C14 | 0.79609 (14) | 0.5331 (7) | 0.4436 (9) | 0.1115 (19)* | |
C15 | 0.83452 (14) | 0.5679 (6) | 0.2884 (9) | 0.1115 (19)* | |
C16 | 0.84778 (14) | 0.3336 (6) | 0.1565 (9) | 0.1115 (19)* | |
C17 | 0.89041 (14) | 0.3540 (6) | 0.0386 (9) | 0.1115 (19)* | |
C18 | 0.90348 (14) | 0.1177 (7) | −0.0907 (9) | 0.1115 (19)* | |
C19 | 0.94545 (14) | 0.1453 (7) | −0.2138 (9) | 0.1115 (19)* | |
C20 | 0.95802 (15) | −0.0860 (6) | −0.3538 (9) | 0.1115 (19)* | |
H31 | 0.5602 (4) | 1.3453 (10) | 1.5638 (17) | 0.120 (2)* | |
H41 | 0.5939 (2) | 0.8628 (10) | 1.552 (3) | 0.120 (2)* | |
H42 | 0.5524 (3) | 0.9401 (11) | 1.7004 (13) | 0.120 (2)* | |
H91 | 0.6877 (3) | 1.2399 (11) | 1.2013 (16) | 0.120 (2)* | |
H92 | 0.6630 (4) | 1.3096 (10) | 0.9375 (15) | 0.120 (2)* | |
H101 | 0.6872 (4) | 0.8239 (10) | 1.0847 (15) | 0.129 (2)* | |
H102 | 0.6610 (3) | 0.8870 (11) | 0.8265 (17) | 0.129 (2)* | |
H111 | 0.7465 (3) | 1.0282 (11) | 0.9472 (17) | 0.129 (2)* | |
H112 | 0.7202 (4) | 1.1043 (10) | 0.6928 (15) | 0.129 (2)* | |
H121 | 0.7442 (4) | 0.6164 (10) | 0.8228 (15) | 0.129 (2)* | |
H122 | 0.7160 (3) | 0.6858 (11) | 0.5736 (17) | 0.129 (2)* | |
H131 | 0.8014 (3) | 0.8427 (11) | 0.6662 (18) | 0.129 (2)* | |
H132 | 0.7732 (4) | 0.8865 (10) | 0.4109 (14) | 0.129 (2)* | |
H141 | 0.8039 (4) | 0.4223 (10) | 0.5839 (14) | 0.129 (2)* | |
H142 | 0.7735 (3) | 0.4568 (11) | 0.3352 (19) | 0.129 (2)* | |
H151 | 0.8583 (3) | 0.6256 (11) | 0.4001 (18) | 0.129 (2)* | |
H152 | 0.8277 (4) | 0.6929 (10) | 0.1600 (15) | 0.129 (2)* | |
H161 | 0.8495 (4) | 0.2001 (9) | 0.2796 (15) | 0.129 (2)* | |
H162 | 0.8260 (3) | 0.2935 (11) | 0.0233 (16) | 0.129 (2)* | |
H171 | 0.9123 (3) | 0.3963 (11) | 0.1707 (16) | 0.129 (2)* | |
H172 | 0.8886 (4) | 0.4858 (9) | −0.0865 (15) | 0.129 (2)* | |
H181 | 0.9064 (4) | −0.0135 (9) | 0.0349 (15) | 0.129 (2)* | |
H182 | 0.8814 (3) | 0.0721 (11) | −0.2203 (17) | 0.129 (2)* | |
H191 | 0.9677 (3) | 0.1835 (11) | −0.0821 (16) | 0.129 (2)* | |
H192 | 0.9431 (4) | 0.2817 (9) | −0.3336 (16) | 0.129 (2)* | |
H201 | 0.9750 (3) | −0.0403 (11) | −0.4933 (15) | 0.129 (2)* | |
H202 | 0.9746 (3) | −0.1938 (10) | −0.2371 (17) | 0.129 (2)* | |
H203 | 0.9325 (2) | −0.1718 (10) | −0.420 (2) | 0.129 (2)* | |
H21 | 0.5245 (5) | 1.2668 (10) | 1.134 (2) | 0.120 (2)* |
Geometric parameters (Å, º) top
C1—N2 | 1.342 (18) | C12—H121 | 0.960 (6) |
C1—C4 | 1.504 (6) | C12—H122 | 0.960 (6) |
C1—O5 | 1.227 (14) | C13—C12 | 1.509 (5) |
N2—C1 | 1.342 (18) | C13—C14 | 1.506 (4) |
N2—C3 | 1.477 (5) | C13—H131 | 0.960 (6) |
N2—H21 | 0.960 (7) | C13—H132 | 0.960 (6) |
C3—N2 | 1.477 (5) | C14—C13 | 1.506 (4) |
C3—C4 | 1.543 (4) | C14—C15 | 1.502 (5) |
C3—C6 | 1.505 (5) | C14—H141 | 0.960 (6) |
C3—H31 | 0.960 (6) | C14—H142 | 0.960 (6) |
C4—C1 | 1.504 (6) | C15—C14 | 1.502 (5) |
C4—C3 | 1.543 (4) | C15—C16 | 1.503 (4) |
C4—H41 | 0.960 (6) | C15—H151 | 0.960 (6) |
C4—H42 | 0.960 (6) | C15—H152 | 0.960 (6) |
O5—C1 | 1.227 (14) | C16—C15 | 1.503 (4) |
C6—C3 | 1.505 (5) | C16—C17 | 1.504 (5) |
C6—O7 | 1.229 (5) | C16—H161 | 0.960 (6) |
C6—O8 | 1.322 (5) | C16—H162 | 0.960 (6) |
O7—C6 | 1.229 (5) | C17—C16 | 1.504 (5) |
O8—C6 | 1.322 (5) | C17—C18 | 1.504 (4) |
O8—C9 | 1.448 (5) | C17—H171 | 0.960 (6) |
C9—O8 | 1.448 (5) | C17—H172 | 0.960 (6) |
C9—C10 | 1.506 (4) | C18—C17 | 1.504 (4) |
C9—H91 | 0.960 (6) | C18—C19 | 1.502 (5) |
C9—H92 | 0.960 (6) | C18—H181 | 0.960 (6) |
C10—C9 | 1.506 (4) | C18—H182 | 0.960 (6) |
C10—C11 | 1.505 (5) | C19—C18 | 1.502 (5) |
C10—H101 | 0.960 (6) | C19—C20 | 1.504 (4) |
C10—H102 | 0.960 (6) | C19—H191 | 0.960 (6) |
C11—C10 | 1.505 (5) | C19—H192 | 0.961 (6) |
C11—C12 | 1.505 (4) | C20—C19 | 1.504 (4) |
C11—H111 | 0.960 (6) | C20—H201 | 0.961 (7) |
C11—H112 | 0.960 (6) | C20—H202 | 0.961 (6) |
C12—C11 | 1.505 (4) | C20—H203 | 0.960 (6) |
C12—C13 | 1.509 (5) | ||
N2—C1—C4 | 90.4 (9) | C12—C13—H131 | 108.6 (7) |
N2—C1—O5 | 132.0 (7) | C12—C13—H132 | 108.6 (8) |
C4—C1—O5 | 135.5 (11) | C14—C13—H131 | 108.3 (5) |
C1—N2—C3 | 97.0 (4) | C14—C13—H132 | 108.4 (6) |
C1—N2—H21 | 142.6 (7) | H131—C13—H132 | 108.5 (7) |
C3—N2—H21 | 120.0 (6) | C13—C14—C15 | 113.9 (3) |
N2—C3—C4 | 84.1 (3) | C13—C14—H141 | 108.6 (6) |
N2—C3—C6 | 113.3 (5) | C13—C14—H142 | 108.8 (5) |
N2—C3—H31 | 113.2 (8) | C15—C14—H141 | 108.6 (8) |
C4—C3—C6 | 114.8 (4) | C15—C14—H142 | 108.1 (7) |
C4—C3—H31 | 113.3 (6) | H141—C14—H142 | 108.7 (7) |
C6—C3—H31 | 114.6 (7) | C14—C15—C16 | 113.4 (3) |
C1—C4—C3 | 87.8 (7) | C14—C15—H151 | 108.8 (7) |
C1—C4—H41 | 113.3 (8) | C14—C15—H152 | 108.6 (8) |
C1—C4—H42 | 113.3 (7) | C16—C15—H151 | 108.8 (5) |
C3—C4—H41 | 113.4 (5) | C16—C15—H152 | 108.5 (6) |
C3—C4—H42 | 113.3 (5) | H151—C15—H152 | 108.6 (7) |
H41—C4—H42 | 113.3 (8) | C15—C16—C17 | 113.9 (3) |
C3—C6—O7 | 124.7 (5) | C15—C16—H161 | 108.7 (6) |
C3—C6—O8 | 113.1 (4) | C15—C16—H162 | 108.4 (5) |
O7—C6—O8 | 121.3 (5) | C17—C16—H161 | 108.6 (8) |
C6—O8—C9 | 116.9 (4) | C17—C16—H162 | 108.6 (7) |
O8—C9—C10 | 108.5 (3) | H161—C16—H162 | 108.6 (8) |
O8—C9—H91 | 109.4 (7) | C16—C17—C18 | 113.4 (3) |
O8—C9—H92 | 109.4 (8) | C16—C17—H171 | 108.9 (7) |
C10—C9—H91 | 109.9 (5) | C16—C17—H172 | 108.6 (8) |
C10—C9—H92 | 109.8 (6) | C18—C17—H171 | 108.6 (5) |
H91—C9—H92 | 109.9 (7) | C18—C17—H172 | 108.7 (6) |
C9—C10—C11 | 114.0 (3) | H171—C17—H172 | 108.5 (8) |
C9—C10—H101 | 108.3 (6) | C17—C18—C19 | 112.3 (3) |
C9—C10—H102 | 108.4 (5) | C17—C18—H181 | 109.0 (6) |
C11—C10—H101 | 108.8 (8) | C17—C18—H182 | 109.1 (5) |
C11—C10—H102 | 108.7 (7) | C19—C18—H181 | 108.7 (8) |
H101—C10—H102 | 108.5 (7) | C19—C18—H182 | 108.9 (7) |
C10—C11—C12 | 114.0 (3) | H181—C18—H182 | 108.7 (7) |
C10—C11—H111 | 108.5 (7) | C18—C19—C20 | 113.0 (3) |
C10—C11—H112 | 108.3 (8) | C18—C19—H191 | 108.6 (7) |
C12—C11—H111 | 108.7 (5) | C18—C19—H192 | 108.9 (8) |
C12—C11—H112 | 108.5 (6) | C20—C19—H191 | 108.9 (5) |
H111—C11—H112 | 108.7 (7) | C20—C19—H192 | 108.8 (6) |
C11—C12—C13 | 114.6 (3) | H191—C19—H192 | 108.6 (8) |
C11—C12—H121 | 108.3 (6) | C19—C20—H201 | 109.5 (5) |
C11—C12—H122 | 108.3 (5) | C19—C20—H202 | 109.5 (6) |
C13—C12—H121 | 108.3 (8) | C19—C20—H203 | 109.4 (6) |
C13—C12—H122 | 108.6 (7) | H201—C20—H202 | 109.5 (8) |
H121—C12—H122 | 108.6 (7) | H201—C20—H203 | 109.5 (8) |
C12—C13—C14 | 114.5 (3) | H202—C20—H203 | 109.3 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O5i | 0.959 (11) | 2.536 (7) | 3.209 (6) | 127.3 (8) |
N2—H21···O5ii | 0.959 (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
(KD5033_L_16) (S)-4-hexadecyloxycarbonyl-2-azetidinone top
Crystal data top
C20H37NO3 | F(000) = 376 |
Mr = 339.52 | Dx = 1.067 Mg m−3 |
Monoclinic, P21 | Melting point: 349 K |
Hall symbol: P 2yb | µ = 0.07 mm−1 |
a = 37.1586 (3) Å | T = 298 K |
b = 5.35911 (5) Å | Particle morphology: needles |
c = 5.30974 (5) Å | white |
β = 92.1693 (6)° | cylinder, 40 × 1.0 mm |
V = 1056.61 (2) Å3 | Specimen 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 ID31 | Scan method: continuous |
Double crystal Si 111 monochromator | 2θmin = 0.509°, 2θmax = 32.069°, 2θstep = 0.005° |
Specimen mounting: borosilicate glass capillary |
Refinement top
Least-squares matrix: full | 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) = 0.110 #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 = 0.078 | 256 parameters |
Rwp = 0.107 | 185 restraints |
Rexp = 0.049 | 2 constraints |
R(F2) = 0.06998 | H 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 phase | Background 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
x | y | z | Uiso*/Ueq | ||
C1 | 0.4684 (3) | 0.236 (12) | 1.7763 (19) | 0.1073 (16)* | |
C4 | 0.4441 (2) | 0.1744 (13) | 1.9974 (17) | 0.1073 (16)* | |
C3 | 0.4441 (2) | −0.0823 (13) | 1.876 (2) | 0.1073 (16)* | |
N2 | 0.4670 (3) | −0.0024 (13) | 1.6950 (17) | 0.1073 (16)* | |
O5 | 0.4839 (3) | 0.4177 (15) | 1.7047 (15) | 0.1073 (16)* | |
C6 | 0.4085 (2) | −0.1580 (15) | 1.759 (2) | 0.1073 (16)* | |
O7 | 0.3877 (2) | −0.3088 (15) | 1.8531 (17) | 0.1073 (16)* | |
O8 | 0.3962 (2) | 0.0020 (15) | 1.5877 (15) | 0.1073 (16)* | |
C9 | 0.3628 (2) | −0.0581 (14) | 1.4481 (16) | 0.1073 (16)* | |
C10 | 0.3484 (2) | 0.1795 (13) | 1.3235 (16) | 0.0986 (12)* | |
C11 | 0.3146 (2) | 0.1503 (13) | 1.1528 (16) | 0.0986 (12)* | |
C12 | 0.3006 (2) | 0.3937 (14) | 1.0461 (15) | 0.0986 (12)* | |
C13 | 0.2722 (2) | 0.3572 (13) | 0.8375 (16) | 0.0986 (12)* | |
C14 | 0.2569 (2) | 0.5939 (14) | 0.7175 (16) | 0.0986 (12)* | |
C15 | 0.2216 (2) | 0.5494 (14) | 0.5550 (16) | 0.0986 (12)* | |
C16 | 0.2092 (2) | 0.7777 (13) | 0.4102 (16) | 0.0986 (12)* | |
C17 | 0.1806 (2) | 0.7287 (13) | 0.2059 (16) | 0.0986 (12)* | |
C18 | 0.1665 (2) | 0.9652 (14) | 0.0907 (16) | 0.0986 (12)* | |
C19 | 0.1353 (2) | 0.9257 (14) | −0.0886 (17) | 0.0986 (12)* | |
C20 | 0.1241 (2) | 1.1620 (13) | −0.2230 (16) | 0.0986 (12)* | |
C21 | 0.0886 (2) | 1.1365 (14) | −0.3819 (16) | 0.0986 (12)* | |
C22 | 0.0755 (2) | 1.3743 (14) | −0.5033 (16) | 0.0986 (12)* | |
C23 | 0.0479 (2) | 1.3383 (13) | −0.7034 (16) | 0.0986 (12)* | |
C24 | 0.0375 (2) | 1.5813 (14) | −0.8330 (16) | 0.0986 (12)* | |
H41 | 0.4224 (4) | 0.272 (2) | 1.994 (4) | 0.1237 (19)* | |
H42 | 0.4567 (5) | 0.1790 (19) | 2.159 (4) | 0.1237 (19)* | |
H31 | 0.4545 (5) | −0.206 (2) | 1.985 (5) | 0.1237 (19)* | |
H91 | 0.3456 (6) | −0.124 (2) | 1.560 (4) | 0.1237 (19)* | |
H92 | 0.3678 (6) | −0.179 (2) | 1.321 (4) | 0.1237 (19)* | |
H101 | 0.3432 (6) | 0.297 (2) | 1.455 (4) | 0.1134 (15)* | |
H102 | 0.3673 (6) | 0.249 (2) | 1.224 (4) | 0.1134 (15)* | |
H111 | 0.2961 (6) | 0.075 (2) | 1.249 (4) | 0.1134 (15)* | |
H112 | 0.3197 (6) | 0.042 (2) | 1.016 (4) | 0.1134 (15)* | |
H121 | 0.2904 (6) | 0.489 (2) | 1.180 (4) | 0.1134 (15)* | |
H122 | 0.3203 (6) | 0.485 (2) | 0.980 (4) | 0.1134 (15)* | |
H131 | 0.2527 (6) | 0.265 (2) | 0.905 (4) | 0.1134 (15)* | |
H132 | 0.2825 (6) | 0.259 (2) | 0.708 (4) | 0.1134 (15)* | |
H141 | 0.2521 (6) | 0.711 (2) | 0.848 (4) | 0.1134 (15)* | |
H142 | 0.2747 (6) | 0.664 (2) | 0.611 (4) | 0.1134 (15)* | |
H151 | 0.2027 (6) | 0.497 (2) | 0.663 (4) | 0.1134 (15)* | |
H152 | 0.2257 (6) | 0.419 (2) | 0.436 (4) | 0.1134 (15)* | |
H161 | 0.1997 (6) | 0.896 (2) | 0.527 (4) | 0.1134 (15)* | |
H162 | 0.2295 (6) | 0.851 (2) | 0.334 (4) | 0.1134 (15)* | |
H171 | 0.1610 (6) | 0.641 (2) | 0.279 (4) | 0.1134 (15)* | |
H172 | 0.1904 (6) | 0.626 (2) | 0.078 (4) | 0.1134 (15)* | |
H181 | 0.1594 (6) | 1.074 (2) | 0.223 (4) | 0.1134 (15)* | |
H182 | 0.1852 (6) | 1.044 (2) | 0.002 (4) | 0.1134 (15)* | |
H191 | 0.1153 (6) | 0.864 (2) | 0.003 (4) | 0.1134 (15)* | |
H192 | 0.1418 (6) | 0.802 (2) | −0.209 (5) | 0.1134 (15)* | |
H201 | 0.1214 (6) | 1.290 (2) | −0.101 (4) | 0.1134 (15)* | |
H202 | 0.1429 (6) | 1.210 (2) | −0.331 (4) | 0.1134 (15)* | |
H211 | 0.0703 (6) | 1.077 (2) | −0.274 (4) | 0.1134 (15)* | |
H212 | 0.0920 (6) | 1.015 (2) | −0.513 (4) | 0.1134 (15)* | |
H221 | 0.0656 (6) | 1.478 (2) | −0.376 (4) | 0.1134 (15)* | |
H222 | 0.0955 (6) | 1.459 (2) | −0.574 (4) | 0.1134 (15)* | |
H231 | 0.0271 (6) | 1.268 (2) | −0.631 (4) | 0.1134 (15)* | |
H232 | 0.0568 (6) | 1.224 (2) | −0.826 (4) | 0.1134 (15)* | |
H241 | 0.0120 (6) | 1.608 (2) | −0.820 (4) | 0.1134 (15)* | |
H242 | 0.0505 (6) | 1.717 (2) | −0.753 (4) | 0.1134 (15)* | |
H243 | 0.0434 (6) | 1.573 (2) | −1.008 (4) | 0.1134 (15)* | |
H21 | 0.4743 (8) | −0.115 (2) | 1.567 (5) | 0.1237 (19)* |
Geometric parameters (Å, º) top
C1—C4 | 1.55 (2) | C14—H141 | 0.956 (19) |
C1—N2 | 1.35 (6) | C14—H142 | 0.96 (2) |
C1—O5 | 1.20 (6) | C15—C14 | 1.560 (11) |
C4—C1 | 1.55 (2) | C15—C16 | 1.508 (11) |
C4—C3 | 1.519 (11) | C15—H151 | 0.96 (2) |
C4—H41 | 0.960 (14) | C15—H152 | 0.959 (18) |
C4—H42 | 0.97 (2) | C16—C15 | 1.508 (11) |
C3—C4 | 1.519 (11) | C16—C17 | 1.513 (11) |
C3—C6 | 1.496 (12) | C16—H161 | 0.964 (19) |
C3—H31 | 0.95 (2) | C16—H162 | 0.95 (2) |
N2—C1 | 1.35 (6) | C17—C16 | 1.513 (11) |
N2—C3 | 1.377 (13) | C17—C18 | 1.493 (11) |
N2—H21 | 0.96 (2) | C17—H171 | 0.96 (2) |
O5—C1 | 1.20 (6) | C17—H172 | 0.96 (2) |
C6—C3 | 1.496 (12) | C18—C17 | 1.493 (11) |
C6—O7 | 1.238 (12) | C18—C19 | 1.489 (12) |
C6—O8 | 1.317 (12) | C18—H181 | 0.96 (2) |
O7—C6 | 1.238 (12) | C18—H182 | 0.95 (2) |
O8—C6 | 1.317 (12) | C19—C18 | 1.489 (12) |
O8—C9 | 1.457 (11) | C19—C20 | 1.504 (11) |
C9—O8 | 1.457 (11) | C19—H191 | 0.96 (2) |
C9—C10 | 1.523 (11) | C19—H192 | 0.96 (2) |
C9—H91 | 0.96 (2) | C20—C19 | 1.504 (11) |
C9—H92 | 0.960 (19) | C20—C21 | 1.543 (11) |
C10—C9 | 1.523 (11) | C20—H201 | 0.954 (18) |
C10—C11 | 1.531 (11) | C20—H202 | 0.96 (2) |
C10—H101 | 0.965 (19) | C21—C20 | 1.543 (11) |
C10—H102 | 0.97 (2) | C21—C22 | 1.501 (11) |
C11—C10 | 1.531 (11) | C21—H211 | 0.96 (2) |
C11—C12 | 1.506 (10) | C21—H212 | 0.964 (19) |
C11—H111 | 0.96 (2) | C22—C21 | 1.501 (11) |
C11—H112 | 0.96 (2) | C22—C23 | 1.462 (11) |
C12—C11 | 1.506 (10) | C22—H221 | 0.96 (2) |
C12—C13 | 1.514 (11) | C22—H222 | 0.96 (2) |
C12—H121 | 0.97 (2) | C23—C22 | 1.462 (11) |
C12—H122 | 0.96 (2) | C23—C24 | 1.516 (11) |
C13—C12 | 1.514 (11) | C23—H231 | 0.95 (2) |
C13—C14 | 1.520 (11) | C23—H232 | 0.964 (19) |
C13—H131 | 0.96 (2) | C24—C23 | 1.516 (11) |
C13—H132 | 0.96 (2) | C24—H241 | 0.96 (2) |
C14—C13 | 1.520 (11) | C24—H242 | 0.965 (18) |
C14—C15 | 1.560 (11) | C24—H243 | 0.97 (2) |
C4—C1—N2 | 91 (3) | C14—C15—H151 | 109.2 (14) |
C4—C1—O5 | 136 (4) | C14—C15—H152 | 108.7 (14) |
N2—C1—O5 | 132.9 (15) | C16—C15—H151 | 109.0 (12) |
C1—C4—C3 | 82 (2) | C16—C15—H152 | 108.2 (13) |
C1—C4—H41 | 113 (2) | H151—C15—H152 | 108.6 (15) |
C1—C4—H42 | 113.1 (14) | C15—C16—C17 | 114.7 (6) |
C3—C4—H41 | 120.1 (11) | C15—C16—H161 | 108.4 (13) |
C3—C4—H42 | 113.1 (9) | C15—C16—H162 | 108.4 (12) |
H41—C4—H42 | 112.4 (17) | C17—C16—H161 | 108.3 (14) |
C4—C3—N2 | 91.4 (6) | C17—C16—H162 | 108.3 (14) |
C4—C3—C6 | 114.1 (7) | H161—C16—H162 | 108.6 (15) |
C4—C3—H31 | 112.3 (15) | C16—C17—C18 | 111.8 (6) |
N2—C3—C6 | 110.7 (9) | C16—C17—H171 | 108.6 (14) |
N2—C3—H31 | 113.1 (14) | C16—C17—H172 | 109.5 (14) |
C6—C3—H31 | 113.4 (12) | C18—C17—H171 | 108.8 (12) |
C1—N2—C3 | 95.1 (10) | C18—C17—H172 | 109.4 (12) |
C1—N2—H21 | 144.8 (17) | H171—C17—H172 | 108.7 (15) |
C3—N2—H21 | 120.0 (15) | C17—C18—C19 | 113.2 (6) |
C3—C6—O7 | 124.3 (9) | C17—C18—H181 | 108.8 (12) |
C3—C6—O8 | 112.8 (7) | C17—C18—H182 | 109.0 (12) |
O7—C6—O8 | 120.0 (9) | C19—C18—H181 | 108.9 (14) |
C6—O8—C9 | 118.2 (7) | C19—C18—H182 | 108.4 (14) |
O8—C9—C10 | 108.4 (6) | H181—C18—H182 | 108.5 (16) |
O8—C9—H91 | 110.0 (14) | C18—C19—C20 | 112.2 (6) |
O8—C9—H92 | 109.0 (14) | C18—C19—H191 | 108.9 (15) |
C10—C9—H91 | 110.3 (12) | C18—C19—H192 | 108.3 (15) |
C10—C9—H92 | 109.4 (13) | C20—C19—H191 | 108.9 (12) |
H91—C9—H92 | 109.8 (15) | C20—C19—H192 | 109.8 (15) |
C9—C10—C11 | 116.1 (6) | H191—C19—H192 | 108.7 (16) |
C9—C10—H101 | 107.9 (12) | C19—C20—C21 | 113.5 (6) |
C9—C10—H102 | 108.0 (12) | C19—C20—H201 | 108.5 (13) |
C11—C10—H101 | 108.2 (14) | C19—C20—H202 | 108.3 (11) |
C11—C10—H102 | 108.3 (14) | C21—C20—H201 | 109.1 (14) |
H101—C10—H102 | 108.1 (16) | C21—C20—H202 | 108.9 (14) |
C10—C11—C12 | 113.5 (6) | H201—C20—H202 | 108.4 (16) |
C10—C11—H111 | 108.5 (14) | C20—C21—C22 | 114.5 (6) |
C10—C11—H112 | 109.2 (14) | C20—C21—H211 | 108.3 (14) |
C12—C11—H111 | 108.6 (12) | C20—C21—H212 | 108.8 (14) |
C12—C11—H112 | 108.5 (12) | C22—C21—H211 | 108.2 (11) |
H111—C11—H112 | 108.5 (16) | C22—C21—H212 | 108.1 (12) |
C11—C12—C13 | 112.6 (6) | H211—C21—H212 | 108.8 (16) |
C11—C12—H121 | 108.6 (12) | C21—C22—C23 | 114.0 (6) |
C11—C12—H122 | 108.9 (12) | C21—C22—H221 | 108.5 (12) |
C13—C12—H121 | 109.0 (14) | C21—C22—H222 | 108.9 (12) |
C13—C12—H122 | 108.6 (14) | C23—C22—H221 | 108.1 (14) |
H121—C12—H122 | 109.1 (15) | C23—C22—H222 | 108.2 (14) |
C12—C13—C14 | 116.0 (6) | H221—C22—H222 | 109.0 (15) |
C12—C13—H131 | 108.1 (14) | C22—C23—C24 | 112.1 (6) |
C12—C13—H132 | 108.0 (14) | C22—C23—H231 | 108.6 (14) |
C14—C13—H131 | 108.1 (12) | C22—C23—H232 | 109.1 (14) |
C14—C13—H132 | 108.1 (12) | C24—C23—H231 | 108.9 (12) |
H131—C13—H132 | 108.4 (15) | C24—C23—H232 | 109.2 (12) |
C13—C14—C15 | 113.4 (6) | H231—C23—H232 | 108.9 (15) |
C13—C14—H141 | 108.8 (13) | C23—C24—H241 | 109.3 (11) |
C13—C14—H142 | 108.4 (12) | C23—C24—H242 | 109.5 (13) |
C15—C14—H141 | 109.0 (14) | C23—C24—H243 | 109.6 (10) |
C15—C14—H142 | 108.5 (14) | H241—C24—H242 | 109.5 (16) |
H141—C14—H142 | 108.5 (15) | H241—C24—H243 | 109.7 (19) |
C14—C15—C16 | 113.1 (6) | H242—C24—H243 | 109.3 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O5i | 0.96 (2) | 2.17 (3) | 2.883 (14) | 130.7 (17) |
Symmetry code: (i) −x+1, y−1/2, −z+3. |