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The dipeptide
L-Ile-
L-Ile has been crystallized in four different protonation states, including as a cation, a zwitterion and an anion, as well as a dimeric cation in which two peptide molecules, linked by a strong –COO
H
OOC– hydrogen bond, share an overall positive charge of +1. This unprecedented series of crystal structures exhibits differences in hydrogen-bonding capabilities, conformational properties and molecular packing arrangements. The crystallization of
L-Ile-
L-Ile as an anion was achieved by slow evaporation from an NH
3(l) solution to give the first ever ammonium salt of a peptide (or amino acid).
Supporting information
CCDC references: 230151; 230152; 230153; 230154
For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
(IIc)
L-Isoleucyl-
L-isoleucine nitrate
top
Crystal data top
C13.08H25N3O6 | Dx = 1.238 Mg m−3 |
Mr = 320.36 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P3121 | Cell parameters from 4175 reflections |
a = 16.0682 (6) Å | θ = 2.3–26.4° |
c = 11.5317 (9) Å | µ = 0.10 mm−1 |
V = 2578.4 (2) Å3 | T = 105 K |
Z = 6 | Rod, colourless |
F(000) = 1035 | 0.25 × 0.06 × 0.05 mm |
Data collection top
Siemens SMART CCD diffractometer | 3401 independent reflections |
Radiation source: fine-focus sealed tube | 2352 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.116 |
Detector resolution: 8.3 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −20→19 |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | k = −20→18 |
Tmin = 0.968, Tmax = 0.995 | l = −11→14 |
11629 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.0975P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3401 reflections | Δρmax = 0.35 e Å−3 |
245 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1.8 (19) |
Crystal data top
C13.08H25N3O6 | Z = 6 |
Mr = 320.36 | Mo Kα radiation |
Trigonal, P3121 | µ = 0.10 mm−1 |
a = 16.0682 (6) Å | T = 105 K |
c = 11.5317 (9) Å | 0.25 × 0.06 × 0.05 mm |
V = 2578.4 (2) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 3401 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | 2352 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.995 | Rint = 0.116 |
11629 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.181 | Δρmax = 0.35 e Å−3 |
S = 1.06 | Δρmin = −0.35 e Å−3 |
3401 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
245 parameters | Absolute structure parameter: −1.8 (19) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.60602 (18) | 0.28975 (17) | 0.3384 (2) | 0.0357 (6) | |
O2A | 0.5928 (2) | 0.08805 (17) | 0.2300 (2) | 0.0381 (7) | |
H5A | 0.573 (3) | 0.068 (3) | 0.167 (4) | 0.057* | |
O3A | 0.70123 (18) | 0.22854 (16) | 0.15079 (19) | 0.0342 (6) | |
N1A | 0.5590 (2) | 0.3424 (2) | 0.5402 (3) | 0.0415 (8) | |
H1A | 0.6242 | 0.3800 | 0.5413 | 0.062* | |
H2A | 0.5344 | 0.3494 | 0.6082 | 0.062* | |
H3A | 0.5347 | 0.3604 | 0.4802 | 0.062* | |
N2A | 0.6417 (2) | 0.1926 (2) | 0.4402 (2) | 0.0296 (6) | |
H4A | 0.6288 | 0.1543 | 0.5004 | 0.036* | |
C1A | 0.5327 (3) | 0.2404 (3) | 0.5255 (3) | 0.0334 (8) | |
H11A | 0.5487 | 0.2172 | 0.5981 | 0.040* | |
C2A | 0.4250 (3) | 0.1781 (3) | 0.5003 (3) | 0.0353 (9) | |
H21A | 0.4077 | 0.2106 | 0.4388 | 0.042* | |
C3A | 0.4031 (3) | 0.0807 (3) | 0.4546 (4) | 0.0557 (12) | |
H31A | 0.4406 | 0.0893 | 0.3841 | 0.084* | |
H32A | 0.3344 | 0.0421 | 0.4369 | 0.084* | |
H33A | 0.4202 | 0.0478 | 0.5135 | 0.084* | |
C4A | 0.3660 (3) | 0.1688 (3) | 0.6095 (3) | 0.0372 (9) | |
H41A | 0.3791 | 0.1323 | 0.6688 | 0.045* | |
H42A | 0.3881 | 0.2338 | 0.6410 | 0.045* | |
C5A | 0.2591 (3) | 0.1199 (3) | 0.5903 (4) | 0.0517 (11) | |
H51A | 0.2276 | 0.1222 | 0.6620 | 0.078* | |
H52A | 0.2350 | 0.0528 | 0.5681 | 0.078* | |
H53A | 0.2453 | 0.1530 | 0.5284 | 0.078* | |
C6A | 0.5964 (2) | 0.2417 (3) | 0.4274 (3) | 0.0289 (8) | |
C7A | 0.7130 (2) | 0.2015 (3) | 0.3549 (3) | 0.0300 (8) | |
H71A | 0.7654 | 0.2703 | 0.3524 | 0.036* | |
C8A | 0.7570 (3) | 0.1402 (3) | 0.3898 (3) | 0.0336 (8) | |
H81A | 0.7038 | 0.0730 | 0.4041 | 0.040* | |
C9A | 0.8210 (3) | 0.1384 (3) | 0.2911 (3) | 0.0423 (10) | |
H91A | 0.7809 | 0.1043 | 0.2241 | 0.063* | |
H92A | 0.8547 | 0.1052 | 0.3179 | 0.063* | |
H93A | 0.8681 | 0.2044 | 0.2688 | 0.063* | |
C10A | 0.8156 (3) | 0.1798 (3) | 0.5032 (3) | 0.0390 (9) | |
H12A | 0.8766 | 0.2393 | 0.4852 | 0.047* | |
H13A | 0.7789 | 0.1969 | 0.5577 | 0.047* | |
C11A | 0.8381 (4) | 0.1090 (4) | 0.5616 (4) | 0.0599 (12) | |
H14A | 0.8773 | 0.1387 | 0.6307 | 0.090* | |
H15A | 0.8735 | 0.0909 | 0.5077 | 0.090* | |
H16A | 0.7780 | 0.0516 | 0.5842 | 0.090* | |
C12A | 0.6664 (3) | 0.1737 (2) | 0.2344 (3) | 0.0296 (8) | |
O1B | 0.4907 (4) | 0.5561 (4) | 0.3174 (4) | 0.0335 (11) | 0.50 |
O2B | 0.5749 (4) | 0.5444 (4) | 0.4564 (5) | 0.0459 (14) | 0.50 |
O3B | 0.5142 (6) | 0.4340 (5) | 0.3252 (7) | 0.0320 (17) | 0.50 |
N1B | 0.5259 (4) | 0.5112 (4) | 0.3655 (5) | 0.0297 (13) | 0.50 |
O1C | 0.4175 (5) | 0.4683 (5) | 0.3189 (4) | 0.0493 (17) | 0.50 |
O2C | 0.3875 (4) | 0.3783 (4) | 0.4708 (4) | 0.0406 (15) | 0.50 |
O3C | 0.4942 (6) | 0.3893 (6) | 0.3465 (7) | 0.0385 (18) | 0.50 |
N1C | 0.4329 (4) | 0.4118 (5) | 0.3785 (6) | 0.0373 (15) | 0.50 |
C1D | 0.0000 | 0.004 (2) | 0.6667 | 0.086 (3)* | 0.43 (4) |
C2D | 0.0188 (9) | −0.0011 (11) | 0.7986 (15) | 0.086 (3)* | 0.496 (15) |
C3D | −0.0050 (13) | −0.0225 (15) | 0.613 (3) | 0.086 (3)* | 0.37 (2) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0476 (16) | 0.0418 (14) | 0.0219 (13) | 0.0255 (12) | 0.0049 (11) | 0.0024 (11) |
O2A | 0.0494 (16) | 0.0280 (13) | 0.0223 (14) | 0.0084 (13) | 0.0055 (12) | 0.0014 (10) |
O3A | 0.0452 (15) | 0.0320 (13) | 0.0210 (13) | 0.0161 (11) | 0.0084 (11) | 0.0053 (10) |
N1A | 0.0271 (15) | 0.0440 (19) | 0.0453 (19) | 0.0116 (14) | 0.0016 (14) | −0.0208 (15) |
N2A | 0.0411 (17) | 0.0334 (14) | 0.0159 (14) | 0.0198 (13) | 0.0073 (12) | 0.0047 (12) |
C1A | 0.037 (2) | 0.040 (2) | 0.0217 (19) | 0.0177 (17) | 0.0016 (15) | −0.0101 (16) |
C2A | 0.037 (2) | 0.040 (2) | 0.022 (2) | 0.0146 (17) | 0.0048 (15) | −0.0050 (16) |
C3A | 0.047 (3) | 0.044 (2) | 0.059 (3) | 0.010 (2) | 0.013 (2) | −0.018 (2) |
C4A | 0.045 (2) | 0.045 (2) | 0.021 (2) | 0.0226 (19) | 0.0085 (16) | −0.0013 (16) |
C5A | 0.048 (2) | 0.059 (3) | 0.040 (2) | 0.020 (2) | 0.0124 (19) | −0.008 (2) |
C6A | 0.0344 (19) | 0.0320 (18) | 0.0172 (18) | 0.0142 (15) | 0.0000 (15) | −0.0063 (15) |
C7A | 0.0368 (19) | 0.0334 (18) | 0.0192 (18) | 0.0170 (15) | 0.0088 (15) | 0.0013 (14) |
C8A | 0.045 (2) | 0.040 (2) | 0.0194 (18) | 0.0240 (17) | 0.0053 (16) | 0.0007 (15) |
C9A | 0.049 (2) | 0.057 (2) | 0.031 (2) | 0.034 (2) | 0.0064 (18) | 0.0002 (18) |
C10A | 0.050 (2) | 0.042 (2) | 0.026 (2) | 0.0248 (19) | −0.0019 (17) | −0.0048 (16) |
C11A | 0.092 (4) | 0.074 (3) | 0.033 (3) | 0.056 (3) | −0.011 (2) | −0.005 (2) |
C12A | 0.0406 (19) | 0.0319 (18) | 0.0202 (19) | 0.0210 (17) | 0.0090 (16) | 0.0029 (14) |
O1B | 0.055 (3) | 0.048 (3) | 0.015 (3) | 0.039 (3) | −0.005 (2) | 0.002 (2) |
O2B | 0.046 (3) | 0.055 (3) | 0.035 (3) | 0.023 (3) | −0.019 (2) | −0.008 (2) |
O3B | 0.053 (4) | 0.039 (4) | 0.024 (4) | 0.038 (4) | 0.000 (3) | −0.001 (3) |
N1B | 0.032 (3) | 0.038 (3) | 0.024 (3) | 0.022 (3) | 0.004 (3) | 0.005 (3) |
O1C | 0.078 (4) | 0.100 (5) | 0.013 (3) | 0.077 (5) | 0.000 (3) | 0.003 (3) |
O2C | 0.055 (3) | 0.058 (3) | 0.013 (5) | 0.032 (3) | 0.010 (3) | 0.004 (2) |
O3C | 0.051 (5) | 0.056 (5) | 0.029 (4) | 0.042 (5) | 0.003 (3) | −0.002 (4) |
N1C | 0.041 (4) | 0.055 (4) | 0.031 (4) | 0.036 (3) | −0.014 (3) | −0.011 (3) |
Geometric parameters (Å, º) top
O1A—C6A | 1.246 (4) | C7A—C8A | 1.526 (5) |
O2A—C12A | 1.291 (4) | C7A—C12A | 1.536 (5) |
O2A—H5A | 0.79 (5) | C7A—H71A | 1.0000 |
O3A—C12A | 1.235 (4) | C8A—C9A | 1.544 (5) |
N1A—C1A | 1.484 (5) | C8A—C10A | 1.550 (5) |
N1A—H1A | 0.9100 | C8A—H81A | 1.0000 |
N1A—H2A | 0.9100 | C9A—H91A | 0.9800 |
N1A—H3A | 0.9100 | C9A—H92A | 0.9800 |
N2A—C6A | 1.323 (4) | C9A—H93A | 0.9800 |
N2A—C7A | 1.462 (4) | C10A—C11A | 1.513 (6) |
N2A—H4A | 0.8800 | C10A—H12A | 0.9900 |
C1A—C6A | 1.519 (5) | C10A—H13A | 0.9900 |
C1A—C2A | 1.532 (5) | C11A—H14A | 0.9800 |
C1A—H11A | 1.0000 | C11A—H15A | 0.9800 |
C2A—C3A | 1.516 (6) | C11A—H16A | 0.9800 |
C2A—C4A | 1.538 (5) | O1B—N1B | 1.248 (7) |
C2A—H21A | 1.0000 | O2B—N1B | 1.259 (7) |
C3A—H31A | 0.9800 | O2B—O2Bi | 1.317 (11) |
C3A—H32A | 0.9800 | O3B—N1B | 1.247 (10) |
C3A—H33A | 0.9800 | O1C—N1C | 1.257 (8) |
C4A—C5A | 1.505 (6) | O2C—O2Ci | 0.721 (8) |
C4A—H41A | 0.9900 | O2C—N1C | 1.250 (8) |
C4A—H42A | 0.9900 | O3C—N1C | 1.263 (10) |
C5A—H51A | 0.9800 | C2D—C2Dii | 0.80 (3) |
C5A—H52A | 0.9800 | C3D—C3Diii | 1.25 (8) |
C5A—H53A | 0.9800 | | |
| | | |
C12A—O2A—H5A | 116 (3) | N2A—C6A—C1A | 118.4 (3) |
C1A—N1A—H1A | 109.5 | N2A—C7A—C8A | 110.7 (3) |
C1A—N1A—H2A | 109.5 | N2A—C7A—C12A | 109.6 (3) |
H1A—N1A—H2A | 109.5 | C8A—C7A—C12A | 111.5 (3) |
C1A—N1A—H3A | 109.5 | N2A—C7A—H71A | 108.3 |
H1A—N1A—H3A | 109.5 | C8A—C7A—H71A | 108.3 |
H2A—N1A—H3A | 109.5 | C12A—C7A—H71A | 108.3 |
C6A—N2A—C7A | 120.3 (3) | C7A—C8A—C9A | 110.3 (3) |
C6A—N2A—H4A | 119.9 | C7A—C8A—C10A | 109.9 (3) |
C7A—N2A—H4A | 119.9 | C9A—C8A—C10A | 110.8 (3) |
N1A—C1A—C6A | 104.6 (3) | C7A—C8A—H81A | 108.6 |
N1A—C1A—C2A | 110.4 (3) | C9A—C8A—H81A | 108.6 |
C6A—C1A—C2A | 113.6 (3) | C10A—C8A—H81A | 108.6 |
N1A—C1A—H11A | 109.4 | C8A—C9A—H91A | 109.5 |
C6A—C1A—H11A | 109.4 | C8A—C9A—H92A | 109.5 |
C2A—C1A—H11A | 109.4 | H91A—C9A—H92A | 109.5 |
C3A—C2A—C1A | 110.1 (3) | C8A—C9A—H93A | 109.5 |
C3A—C2A—C4A | 111.7 (3) | H91A—C9A—H93A | 109.5 |
C1A—C2A—C4A | 110.4 (3) | H92A—C9A—H93A | 109.5 |
C3A—C2A—H21A | 108.2 | C11A—C10A—C8A | 113.0 (3) |
C1A—C2A—H21A | 108.2 | C11A—C10A—H12A | 109.0 |
C4A—C2A—H21A | 108.2 | C8A—C10A—H12A | 109.0 |
C2A—C3A—H31A | 109.5 | C11A—C10A—H13A | 109.0 |
C2A—C3A—H32A | 109.5 | C8A—C10A—H13A | 109.0 |
H31A—C3A—H32A | 109.5 | H12A—C10A—H13A | 107.8 |
C2A—C3A—H33A | 109.5 | C10A—C11A—H14A | 109.5 |
H31A—C3A—H33A | 109.5 | C10A—C11A—H15A | 109.5 |
H32A—C3A—H33A | 109.5 | H14A—C11A—H15A | 109.5 |
C5A—C4A—C2A | 114.7 (3) | C10A—C11A—H16A | 109.5 |
C5A—C4A—H41A | 108.6 | H14A—C11A—H16A | 109.5 |
C2A—C4A—H41A | 108.6 | H15A—C11A—H16A | 109.5 |
C5A—C4A—H42A | 108.6 | O3A—C12A—O2A | 125.2 (3) |
C2A—C4A—H42A | 108.6 | O3A—C12A—C7A | 121.2 (3) |
H41A—C4A—H42A | 107.6 | O2A—C12A—C7A | 113.5 (3) |
C4A—C5A—H51A | 109.5 | N1B—O2B—O2Bi | 121.6 (6) |
C4A—C5A—H52A | 109.5 | O3B—N1B—O1B | 121.5 (6) |
H51A—C5A—H52A | 109.5 | O3B—N1B—O2B | 118.9 (6) |
C4A—C5A—H53A | 109.5 | O1B—N1B—O2B | 119.5 (6) |
H51A—C5A—H53A | 109.5 | O2Ci—O2C—N1C | 147.4 (6) |
H52A—C5A—H53A | 109.5 | O2C—N1C—O1C | 119.6 (6) |
O1A—C6A—N2A | 121.8 (3) | O2C—N1C—O3C | 119.7 (7) |
O1A—C6A—C1A | 119.8 (3) | O1C—N1C—O3C | 120.7 (7) |
| | | |
N1A—C1A—C2A—C3A | 165.2 (3) | C6A—N2A—C7A—C8A | 178.6 (3) |
C6A—C1A—C2A—C3A | 48.1 (5) | C6A—N2A—C7A—C12A | −58.0 (4) |
N1A—C1A—C2A—C4A | −71.0 (4) | N2A—C7A—C8A—C9A | 171.8 (3) |
C6A—C1A—C2A—C4A | 171.9 (3) | C12A—C7A—C8A—C9A | 49.5 (4) |
C3A—C2A—C4A—C5A | −64.8 (5) | N2A—C7A—C8A—C10A | −65.7 (4) |
C1A—C2A—C4A—C5A | 172.3 (3) | C12A—C7A—C8A—C10A | 171.9 (3) |
C7A—N2A—C6A—O1A | 6.6 (5) | C7A—C8A—C10A—C11A | 163.9 (3) |
C7A—N2A—C6A—C1A | −172.2 (3) | C9A—C8A—C10A—C11A | −74.0 (4) |
N1A—C1A—C6A—O1A | −45.0 (4) | N2A—C7A—C12A—O3A | 126.1 (3) |
C2A—C1A—C6A—O1A | 75.4 (4) | C8A—C7A—C12A—O3A | −111.0 (4) |
N1A—C1A—C6A—N2A | 133.8 (3) | N2A—C7A—C12A—O2A | −57.3 (4) |
C2A—C1A—C6A—N2A | −105.8 (4) | C8A—C7A—C12A—O2A | 65.6 (4) |
Symmetry codes: (i) y, x, −z+1; (ii) x−y, −y, −z+5/3; (iii) −x, −x+y, −z+4/3. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H5A···O1Biv | 0.79 (5) | 2.01 (5) | 2.745 (5) | 153 (5) |
O2A—H5A···O1Civ | 0.79 (5) | 1.80 (5) | 2.543 (5) | 156 (5) |
N1A—H1A···O3Av | 0.91 | 2.17 | 3.051 (4) | 161 |
N1A—H2A···O1Bi | 0.91 | 2.29 | 2.914 (6) | 126 |
N1A—H2A···O1Ci | 0.91 | 2.05 | 2.824 (6) | 142 |
N1A—H2A···O3Avi | 0.91 | 2.53 | 3.258 (4) | 137 |
N1A—H3A···O2C | 0.91 | 2.52 | 3.187 (8) | 130 |
N1A—H3A···O3B | 0.91 | 2.26 | 3.146 (8) | 165 |
N1A—H3A···O3C | 0.91 | 1.82 | 2.726 (9) | 172 |
N2A—H4A···O3Bv | 0.88 | 2.14 | 2.981 (8) | 161 |
N2A—H4A···O3Cv | 0.88 | 2.18 | 3.028 (4) | 161 |
C1A—H11A···O1Av | 1.00 | 2.42 | 2.999 (4) | 116 |
C1A—H11A···O3Bv | 1.00 | 2.45 | 3.262 (9) | 138 |
Symmetry codes: (i) y, x, −z+1; (iv) −x+1, −x+y, −z+1/3; (v) −y+1, x−y, z+1/3; (vi) −x+y+1, −x+1, z+2/3. |
(IIdc)
L-Isoleucyl-
L-isoleucine
L-Isoleucyl-
L-isoleucinium nitrate acetonitrile solvate
top
Crystal data top
C13.80H27.20N3.40O4.70 | Dx = 1.147 Mg m−3 |
Mr = 315.99 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P21212 | Cell parameters from 3710 reflections |
a = 16.2957 (19) Å | θ = 2.1–25.1° |
b = 23.426 (2) Å | µ = 0.09 mm−1 |
c = 9.5842 (9) Å | T = 105 K |
V = 3658.7 (7) Å3 | Plate, colourless |
Z = 8 | 0.55 × 0.42 × 0.05 mm |
F(000) = 1371 | |
Data collection top
Siemens SMART CCD diffractometer | 3657 independent reflections |
Radiation source: fine-focus sealed tube | 3276 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 8.3 pixels mm-1 | θmax = 25.1°, θmin = 2.1° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −15→19 |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | k = −27→27 |
Tmin = 0.804, Tmax = 0.996 | l = −10→11 |
27666 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0659P)2 + 1.4323P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.007 |
3657 reflections | Δρmax = 0.21 e Å−3 |
449 parameters | Δρmin = −0.31 e Å−3 |
48 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −4.9 (15) |
Crystal data top
C13.80H27.20N3.40O4.70 | V = 3658.7 (7) Å3 |
Mr = 315.99 | Z = 8 |
Orthorhombic, P21212 | Mo Kα radiation |
a = 16.2957 (19) Å | µ = 0.09 mm−1 |
b = 23.426 (2) Å | T = 105 K |
c = 9.5842 (9) Å | 0.55 × 0.42 × 0.05 mm |
Data collection top
Siemens SMART CCD diffractometer | 3657 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | 3276 reflections with I > 2σ(I) |
Tmin = 0.804, Tmax = 0.996 | Rint = 0.043 |
27666 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.129 | Δρmax = 0.21 e Å−3 |
S = 1.14 | Δρmin = −0.31 e Å−3 |
3657 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
449 parameters | Absolute structure parameter: −4.9 (15) |
48 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.71955 (13) | 0.75538 (10) | 0.2910 (2) | 0.0329 (5) | |
O2A | 0.52869 (12) | 0.79839 (10) | −0.0783 (2) | 0.0299 (5) | |
O3A | 0.46408 (12) | 0.80128 (9) | 0.1229 (2) | 0.0274 (5) | |
N1A | 0.86800 (14) | 0.73828 (11) | 0.1502 (3) | 0.0260 (5) | |
H1A | 0.8705 | 0.7749 | 0.1262 | 0.039* | |
H2A | 0.9102 | 0.7196 | 0.1127 | 0.039* | |
H3A | 0.8701 | 0.7352 | 0.2427 | 0.039* | |
N2A | 0.67233 (13) | 0.77711 (10) | 0.0752 (2) | 0.0222 (5) | |
H4A | 0.6760 | 0.7696 | −0.0124 | 0.027* | |
C1A | 0.78946 (16) | 0.71314 (12) | 0.0983 (3) | 0.0228 (6) | |
H11A | 0.7871 | 0.7160 | −0.0037 | 0.027* | |
C2A | 0.78003 (19) | 0.65094 (13) | 0.1428 (3) | 0.0293 (7) | |
H21A | 0.7825 | 0.6495 | 0.2449 | 0.035* | |
C3A | 0.6961 (2) | 0.62952 (17) | 0.0978 (5) | 0.0532 (10) | |
H31A | 0.6542 | 0.6511 | 0.1445 | 0.080* | |
H32A | 0.6907 | 0.5899 | 0.1216 | 0.080* | |
H33A | 0.6903 | 0.6340 | −0.0013 | 0.080* | |
C4A | 0.8490 (2) | 0.61318 (14) | 0.0852 (4) | 0.0372 (8) | |
H41A | 0.8399 | 0.6072 | −0.0138 | 0.045* | |
H42A | 0.9008 | 0.6330 | 0.0959 | 0.045* | |
C5A | 0.8547 (3) | 0.55523 (15) | 0.1573 (4) | 0.0510 (10) | |
H51A | 0.8979 | 0.5332 | 0.1155 | 0.077* | |
H52A | 0.8036 | 0.5353 | 0.1472 | 0.077* | |
H53A | 0.8663 | 0.5607 | 0.2546 | 0.077* | |
C6A | 0.72271 (17) | 0.75045 (13) | 0.1633 (3) | 0.0238 (6) | |
C7A | 0.61117 (16) | 0.81854 (12) | 0.1215 (3) | 0.0234 (6) | |
H71A | 0.6044 | 0.8153 | 0.2228 | 0.028* | |
C8A | 0.63771 (18) | 0.87996 (13) | 0.0854 (3) | 0.0271 (6) | |
H81A | 0.6486 | 0.8816 | −0.0151 | 0.033* | |
C9A | 0.5684 (2) | 0.92237 (14) | 0.1177 (4) | 0.0370 (8) | |
H91A | 0.5858 | 0.9603 | 0.0935 | 0.056* | |
H92A | 0.5556 | 0.9209 | 0.2154 | 0.056* | |
H93A | 0.5206 | 0.9125 | 0.0645 | 0.056* | |
C10A | 0.7166 (2) | 0.89629 (14) | 0.1615 (4) | 0.0360 (7) | |
H12A | 0.7548 | 0.8646 | 0.1561 | 0.043* | |
H13A | 0.7042 | 0.9027 | 0.2592 | 0.043* | |
C11A | 0.7579 (2) | 0.94970 (17) | 0.1024 (5) | 0.0546 (11) | |
H14A | 0.8101 | 0.9552 | 0.1470 | 0.082* | |
H15A | 0.7237 | 0.9823 | 0.1193 | 0.082* | |
H16A | 0.7659 | 0.9452 | 0.0038 | 0.082* | |
C12A | 0.52962 (17) | 0.80423 (12) | 0.0502 (3) | 0.0235 (6) | |
O1B | 0.21085 (12) | 0.77175 (9) | 0.21047 (19) | 0.0278 (5) | |
O2B | 0.40947 (12) | 0.80032 (9) | 0.5776 (2) | 0.0283 (5) | |
O3B | 0.47362 (12) | 0.79735 (10) | 0.3756 (2) | 0.0278 (5) | |
H5B | 0.467 (2) | 0.7965 (15) | 0.259 (4) | 0.042* | |
N1B | 0.06650 (14) | 0.74491 (10) | 0.3461 (2) | 0.0224 (5) | |
H1B | 0.0607 | 0.7818 | 0.3655 | 0.034* | |
H2B | 0.0259 | 0.7253 | 0.3856 | 0.034* | |
H3B | 0.0650 | 0.7399 | 0.2541 | 0.034* | |
N2B | 0.26391 (13) | 0.78810 (10) | 0.4256 (2) | 0.0212 (5) | |
H4B | 0.2589 | 0.7813 | 0.5133 | 0.025* | |
C1B | 0.14657 (16) | 0.72440 (12) | 0.4013 (3) | 0.0218 (6) | |
H11B | 0.1474 | 0.7283 | 0.5031 | 0.026* | |
C2B | 0.16422 (17) | 0.66244 (13) | 0.3609 (3) | 0.0263 (6) | |
H21B | 0.1644 | 0.6600 | 0.2588 | 0.032* | |
C3B | 0.2493 (2) | 0.64503 (14) | 0.4128 (4) | 0.0385 (8) | |
H31B | 0.2589 | 0.6056 | 0.3911 | 0.058* | |
H32B | 0.2523 | 0.6504 | 0.5120 | 0.058* | |
H33B | 0.2902 | 0.6681 | 0.3680 | 0.058* | |
C4B | 0.0975 (2) | 0.62174 (13) | 0.4159 (4) | 0.0342 (7) | |
H41B | 0.1012 | 0.6200 | 0.5168 | 0.041* | |
H42B | 0.0440 | 0.6372 | 0.3923 | 0.041* | |
C5B | 0.1041 (3) | 0.56190 (15) | 0.3576 (5) | 0.0505 (10) | |
H51B | 0.0616 | 0.5385 | 0.3969 | 0.076* | |
H52B | 0.1567 | 0.5461 | 0.3810 | 0.076* | |
H53B | 0.0981 | 0.5631 | 0.2580 | 0.076* | |
C6B | 0.21077 (17) | 0.76373 (12) | 0.3369 (3) | 0.0209 (6) | |
C7B | 0.32985 (16) | 0.82576 (12) | 0.3793 (3) | 0.0219 (6) | |
H71B | 0.3357 | 0.8225 | 0.2778 | 0.026* | |
C8B | 0.31252 (18) | 0.88884 (12) | 0.4177 (3) | 0.0264 (6) | |
H81B | 0.3073 | 0.8909 | 0.5194 | 0.032* | |
C9B | 0.3854 (2) | 0.92630 (14) | 0.3758 (4) | 0.0359 (8) | |
H91B | 0.3738 | 0.9653 | 0.3990 | 0.054* | |
H92B | 0.3945 | 0.9231 | 0.2772 | 0.054* | |
H93B | 0.4336 | 0.9140 | 0.4250 | 0.054* | |
C10B | 0.2319 (2) | 0.91053 (14) | 0.3550 (4) | 0.0379 (8) | |
H12B | 0.2393 | 0.9163 | 0.2555 | 0.045* | |
H13B | 0.1900 | 0.8816 | 0.3673 | 0.045* | |
C11B | 0.2027 (3) | 0.96571 (17) | 0.4201 (5) | 0.0649 (12) | |
H14B | 0.1489 | 0.9747 | 0.3855 | 0.097* | |
H15B | 0.2399 | 0.9959 | 0.3964 | 0.097* | |
H16B | 0.2006 | 0.9615 | 0.5196 | 0.097* | |
C12B | 0.40893 (17) | 0.80596 (12) | 0.4486 (3) | 0.0213 (6) | |
O1C | 0.4221 (5) | 0.5919 (3) | 0.5904 (10) | 0.0579 (18)* | 0.402 (9) |
O2C | 0.4382 (5) | 0.6684 (3) | 0.7244 (10) | 0.0326 (13)* | 0.402 (9) |
O3C | 0.5341 (9) | 0.6419 (8) | 0.586 (2) | 0.046 (3) | 0.402 (9) |
N1C | 0.4630 (5) | 0.6351 (4) | 0.6374 (11) | 0.066 (3) | 0.402 (9) |
O4C | 0.4125 (7) | 0.5981 (4) | 0.6358 (13) | 0.0579 (18)* | 0.324 (9) |
O5C | 0.4595 (5) | 0.6669 (3) | 0.7742 (10) | 0.0326 (13)* | 0.324 (9) |
O6C | 0.5202 (12) | 0.6478 (10) | 0.581 (2) | 0.046 (3) | 0.324 (9) |
N2C | 0.4631 (6) | 0.6384 (5) | 0.6687 (13) | 0.066 (3) | 0.324 (9) |
O1D | 0.5770 (10) | 0.6682 (12) | 0.442 (2) | 0.031 (5)* | 0.072 (3) |
O2D | 0.4415 (9) | 0.6741 (12) | 0.422 (2) | 0.031 (5)* | 0.072 (3) |
O3D | 0.5183 (14) | 0.6776 (13) | 0.2403 (15) | 0.031 (5)* | 0.072 (3) |
N1D | 0.5098 (10) | 0.6729 (14) | 0.3715 (16) | 0.025* | 0.072 (3) |
O7C | 0.4192 (10) | 0.6775 (5) | 0.671 (2) | 0.056 (4)* | 0.188 (9) |
O8C | 0.4423 (10) | 0.5842 (5) | 0.6772 (18) | 0.056 (4)* | 0.188 (9) |
O9C | 0.5259 (17) | 0.6401 (11) | 0.572 (5) | 0.056 (4)* | 0.188 (9) |
N3C | 0.4595 (9) | 0.6320 (7) | 0.638 (2) | 0.026* | 0.188 (9) |
N1E | 0.3627 (3) | 0.67250 (18) | 0.0672 (4) | 0.0772 (15) | 0.928 (3) |
C1E | 0.4074 (3) | 0.6583 (2) | 0.1440 (5) | 0.0602 (13) | 0.928 (3) |
C2E | 0.4675 (4) | 0.6426 (3) | 0.2515 (6) | 0.096 (2) | 0.928 (3) |
H1E | 0.5087 | 0.6184 | 0.2112 | 0.144* | 0.928 (3) |
H2E | 0.4403 | 0.6227 | 0.3257 | 0.144* | 0.928 (3) |
H3E | 0.4928 | 0.6765 | 0.2877 | 0.144* | 0.928 (3) |
N1F | 0.3679 (5) | 0.5112 (4) | 0.2345 (9) | 0.086 (3)* | 0.483 (6) |
C1F | 0.4174 (5) | 0.5097 (4) | 0.3116 (9) | 0.061 (3)* | 0.483 (6) |
C2F | 0.4842 (6) | 0.5057 (6) | 0.4131 (9) | 0.075 (3)* | 0.483 (6) |
H1F | 0.5351 | 0.5153 | 0.3687 | 0.112* | 0.483 (6) |
H2F | 0.4872 | 0.4674 | 0.4487 | 0.112* | 0.483 (6) |
H3F | 0.4741 | 0.5317 | 0.4886 | 0.112* | 0.483 (6) |
N1G | 0.5794 (8) | 0.5053 (6) | 0.0982 (12) | 0.094 (4)* | 0.401 (9) |
C1G | 0.5413 (9) | 0.5034 (7) | 0.0038 (14) | 0.095 (5)* | 0.401 (9) |
C2G | 0.5024 (18) | 0.5133 (11) | −0.1324 (15) | 0.117 (7)* | 0.401 (9) |
H1G | 0.5428 | 0.5268 | −0.1974 | 0.176* | 0.401 (9) |
H2G | 0.4598 | 0.5413 | −0.1227 | 0.176* | 0.401 (9) |
H3G | 0.4792 | 0.4782 | −0.1661 | 0.176* | 0.401 (9) |
O1W | 0.505 (2) | 0.5516 (15) | 0.894 (3) | 0.28 (2)* | 0.39 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0309 (12) | 0.0534 (14) | 0.0145 (10) | 0.0132 (11) | 0.0004 (8) | 0.0009 (9) |
O2A | 0.0215 (10) | 0.0539 (13) | 0.0143 (9) | 0.0032 (10) | −0.0013 (8) | −0.0046 (10) |
O3A | 0.0179 (9) | 0.0457 (12) | 0.0186 (9) | 0.0003 (9) | 0.0011 (8) | −0.0010 (9) |
N1A | 0.0222 (12) | 0.0359 (13) | 0.0200 (12) | 0.0041 (10) | −0.0016 (10) | 0.0002 (11) |
N2A | 0.0161 (11) | 0.0362 (13) | 0.0144 (10) | 0.0033 (10) | −0.0005 (9) | −0.0008 (10) |
C1A | 0.0190 (13) | 0.0353 (16) | 0.0142 (13) | 0.0027 (12) | −0.0010 (11) | 0.0016 (11) |
C2A | 0.0306 (16) | 0.0358 (16) | 0.0214 (14) | 0.0003 (13) | 0.0066 (13) | 0.0014 (13) |
C3A | 0.038 (2) | 0.047 (2) | 0.074 (3) | −0.0097 (17) | 0.004 (2) | 0.000 (2) |
C4A | 0.0408 (19) | 0.0346 (17) | 0.0363 (18) | 0.0058 (15) | 0.0102 (16) | 0.0034 (15) |
C5A | 0.068 (3) | 0.0368 (18) | 0.049 (2) | 0.0099 (18) | 0.012 (2) | 0.0052 (17) |
C6A | 0.0200 (14) | 0.0360 (15) | 0.0156 (13) | 0.0011 (12) | −0.0004 (11) | 0.0043 (12) |
C7A | 0.0180 (13) | 0.0350 (16) | 0.0173 (13) | 0.0035 (11) | −0.0015 (11) | −0.0006 (12) |
C8A | 0.0223 (14) | 0.0373 (16) | 0.0218 (14) | 0.0018 (13) | −0.0004 (12) | 0.0005 (13) |
C9A | 0.0338 (17) | 0.0346 (17) | 0.0427 (19) | 0.0032 (14) | 0.0018 (16) | 0.0007 (15) |
C10A | 0.0302 (17) | 0.0410 (18) | 0.0369 (17) | −0.0057 (14) | −0.0046 (15) | −0.0021 (15) |
C11A | 0.038 (2) | 0.054 (2) | 0.072 (3) | −0.0158 (17) | −0.006 (2) | 0.000 (2) |
C12A | 0.0191 (14) | 0.0306 (15) | 0.0208 (15) | 0.0019 (12) | 0.0012 (11) | 0.0013 (12) |
O1B | 0.0249 (10) | 0.0447 (12) | 0.0139 (9) | −0.0084 (10) | −0.0011 (8) | 0.0013 (8) |
O2B | 0.0192 (10) | 0.0495 (13) | 0.0162 (9) | −0.0001 (9) | −0.0009 (8) | 0.0055 (9) |
O3B | 0.0189 (10) | 0.0464 (12) | 0.0181 (9) | 0.0023 (9) | 0.0031 (8) | 0.0021 (9) |
N1B | 0.0185 (11) | 0.0311 (12) | 0.0175 (11) | −0.0038 (10) | 0.0001 (9) | −0.0007 (10) |
N2B | 0.0175 (11) | 0.0338 (13) | 0.0122 (10) | −0.0038 (10) | 0.0009 (9) | 0.0032 (10) |
C1B | 0.0176 (13) | 0.0336 (15) | 0.0142 (13) | 0.0003 (12) | −0.0009 (11) | −0.0004 (11) |
C2B | 0.0240 (15) | 0.0350 (16) | 0.0200 (14) | 0.0013 (12) | 0.0008 (12) | 0.0002 (12) |
C3B | 0.0270 (16) | 0.0388 (18) | 0.050 (2) | 0.0043 (14) | 0.0019 (16) | 0.0077 (17) |
C4B | 0.0329 (17) | 0.0325 (16) | 0.0371 (18) | −0.0036 (14) | 0.0060 (15) | −0.0010 (15) |
C5B | 0.056 (2) | 0.0339 (18) | 0.061 (2) | −0.0048 (17) | 0.011 (2) | −0.0038 (18) |
C6B | 0.0160 (13) | 0.0300 (15) | 0.0168 (13) | 0.0009 (12) | 0.0009 (11) | 0.0004 (12) |
C7B | 0.0196 (13) | 0.0312 (14) | 0.0148 (13) | −0.0027 (11) | 0.0018 (11) | 0.0028 (11) |
C8B | 0.0240 (15) | 0.0314 (15) | 0.0238 (14) | 0.0002 (12) | 0.0000 (12) | 0.0009 (13) |
C9B | 0.0359 (17) | 0.0316 (17) | 0.0403 (18) | −0.0058 (14) | −0.0018 (15) | 0.0018 (15) |
C10B | 0.0340 (17) | 0.0353 (17) | 0.0444 (19) | 0.0061 (14) | −0.0040 (16) | 0.0076 (16) |
C11B | 0.060 (3) | 0.058 (2) | 0.077 (3) | 0.028 (2) | −0.005 (3) | −0.002 (2) |
C12B | 0.0192 (14) | 0.0262 (14) | 0.0185 (14) | −0.0033 (12) | −0.0005 (11) | 0.0015 (11) |
O3C | 0.023 (5) | 0.037 (4) | 0.077 (4) | 0.001 (4) | 0.005 (4) | −0.019 (3) |
N1C | 0.045 (3) | 0.029 (3) | 0.123 (8) | −0.015 (2) | 0.012 (4) | −0.009 (4) |
O6C | 0.023 (5) | 0.037 (4) | 0.077 (4) | 0.001 (4) | 0.005 (4) | −0.019 (3) |
N2C | 0.045 (3) | 0.029 (3) | 0.123 (8) | −0.015 (2) | 0.012 (4) | −0.009 (4) |
N1E | 0.122 (4) | 0.061 (2) | 0.049 (2) | −0.021 (3) | −0.034 (3) | 0.024 (2) |
C1E | 0.075 (3) | 0.055 (3) | 0.051 (3) | −0.005 (2) | 0.014 (3) | 0.008 (2) |
C2E | 0.073 (4) | 0.121 (5) | 0.094 (5) | 0.032 (4) | −0.011 (4) | 0.015 (4) |
Geometric parameters (Å, º) top
O1A—C6A | 1.230 (3) | C2B—C4B | 1.539 (4) |
O2A—C12A | 1.239 (3) | C2B—H21B | 0.9800 |
O3A—C12A | 1.277 (3) | C3B—H31B | 0.9600 |
O3A—H5B | 1.31 (4) | C3B—H32B | 0.9600 |
N1A—C1A | 1.494 (4) | C3B—H33B | 0.9600 |
N1A—H1A | 0.8900 | C4B—C5B | 1.513 (5) |
N1A—H2A | 0.8900 | C4B—H41B | 0.9700 |
N1A—H3A | 0.8900 | C4B—H42B | 0.9700 |
N2A—C6A | 1.333 (4) | C5B—H51B | 0.9600 |
N2A—C7A | 1.460 (3) | C5B—H52B | 0.9600 |
N2A—H4A | 0.8600 | C5B—H53B | 0.9600 |
C1A—C2A | 1.526 (4) | C7B—C12B | 1.522 (4) |
C1A—C6A | 1.529 (4) | C7B—C8B | 1.549 (4) |
C1A—H11A | 0.9800 | C7B—H71B | 0.9800 |
C2A—C3A | 1.520 (5) | C8B—C9B | 1.530 (4) |
C2A—C4A | 1.533 (4) | C8B—C10B | 1.531 (4) |
C2A—H21A | 0.9800 | C8B—H81B | 0.9800 |
C3A—H31A | 0.9600 | C9B—H91B | 0.9600 |
C3A—H32A | 0.9600 | C9B—H92B | 0.9600 |
C3A—H33A | 0.9600 | C9B—H93B | 0.9600 |
C4A—C5A | 1.526 (5) | C10B—C11B | 1.512 (5) |
C4A—H41A | 0.9700 | C10B—H12B | 0.9700 |
C4A—H42A | 0.9700 | C10B—H13B | 0.9700 |
C5A—H51A | 0.9600 | C11B—H14B | 0.9600 |
C5A—H52A | 0.9600 | C11B—H15B | 0.9600 |
C5A—H53A | 0.9600 | C11B—H16B | 0.9600 |
C7A—C12A | 1.531 (4) | O1C—N1C | 1.292 (10) |
C7A—C8A | 1.542 (4) | O2C—N1C | 1.212 (9) |
C7A—H71A | 0.9800 | O3C—N1C | 1.270 (6) |
C8A—C10A | 1.527 (4) | O4C—N2C | 1.292 (10) |
C8A—C9A | 1.535 (4) | O5C—N2C | 1.212 (10) |
C8A—H81A | 0.9800 | O6C—N2C | 1.270 (6) |
C9A—H91A | 0.9600 | O1D—N1D | 1.291 (10) |
C9A—H92A | 0.9600 | O2D—N1D | 1.212 (10) |
C9A—H93A | 0.9600 | O3D—N1D | 1.270 (7) |
C10A—C11A | 1.529 (5) | O7C—N3C | 1.292 (11) |
C10A—H12A | 0.9700 | O8C—N3C | 1.213 (10) |
C10A—H13A | 0.9700 | O9C—N3C | 1.270 (6) |
C11A—H14A | 0.9600 | N1E—C1E | 1.087 (6) |
C11A—H15A | 0.9600 | C1E—C2E | 1.468 (7) |
C11A—H16A | 0.9600 | C2E—H1E | 0.9600 |
O1B—C6B | 1.226 (3) | C2E—H2E | 0.9600 |
O2B—C12B | 1.243 (3) | C2E—H3E | 0.9600 |
O3B—C12B | 1.281 (3) | N1F—C1F | 1.095 (6) |
O3B—H5B | 1.13 (4) | C1F—C2F | 1.463 (7) |
N1B—C1B | 1.488 (3) | C1F—C2Fi | 1.910 (14) |
N1B—H1B | 0.8900 | C2F—H1F | 0.9600 |
N1B—H2B | 0.8900 | C2F—H2F | 0.9600 |
N1B—H3B | 0.8900 | C2F—H3F | 0.9600 |
N2B—C6B | 1.341 (4) | N1G—C1G | 1.098 (7) |
N2B—C7B | 1.459 (3) | C1G—C1Gi | 1.35 (3) |
N2B—H4B | 0.8600 | C1G—C2G | 1.470 (8) |
C1B—C6B | 1.524 (4) | C1G—C2Gi | 1.54 (3) |
C1B—C2B | 1.530 (4) | C2G—H1G | 0.9600 |
C1B—H11B | 0.9800 | C2G—H2G | 0.9600 |
C2B—C3B | 1.529 (4) | C2G—H3G | 0.9600 |
| | | |
C12A—O3A—H5B | 121.4 (15) | C6B—C1B—H11B | 109.7 |
C1A—N1A—H1A | 109.5 | C2B—C1B—H11B | 109.7 |
C1A—N1A—H2A | 109.5 | C3B—C2B—C1B | 110.0 (3) |
H1A—N1A—H2A | 109.5 | C3B—C2B—C4B | 111.4 (3) |
C1A—N1A—H3A | 109.5 | C1B—C2B—C4B | 111.6 (2) |
H1A—N1A—H3A | 109.5 | C3B—C2B—H21B | 107.9 |
H2A—N1A—H3A | 109.5 | C1B—C2B—H21B | 107.9 |
C6A—N2A—C7A | 122.6 (2) | C4B—C2B—H21B | 107.9 |
C6A—N2A—H4A | 118.7 | C2B—C3B—H31B | 109.5 |
C7A—N2A—H4A | 118.7 | C2B—C3B—H32B | 109.5 |
N1A—C1A—C2A | 111.7 (2) | H31B—C3B—H32B | 109.5 |
N1A—C1A—C6A | 104.4 (2) | C2B—C3B—H33B | 109.5 |
C2A—C1A—C6A | 111.1 (2) | H31B—C3B—H33B | 109.5 |
N1A—C1A—H11A | 109.9 | H32B—C3B—H33B | 109.5 |
C2A—C1A—H11A | 109.9 | C5B—C4B—C2B | 113.5 (3) |
C6A—C1A—H11A | 109.9 | C5B—C4B—H41B | 108.9 |
C3A—C2A—C1A | 109.0 (3) | C2B—C4B—H41B | 108.9 |
C3A—C2A—C4A | 111.5 (3) | C5B—C4B—H42B | 108.9 |
C1A—C2A—C4A | 112.1 (2) | C2B—C4B—H42B | 108.9 |
C3A—C2A—H21A | 108.0 | H41B—C4B—H42B | 107.7 |
C1A—C2A—H21A | 108.0 | C4B—C5B—H51B | 109.5 |
C4A—C2A—H21A | 108.0 | C4B—C5B—H52B | 109.5 |
C2A—C3A—H31A | 109.5 | H51B—C5B—H52B | 109.5 |
C2A—C3A—H32A | 109.5 | C4B—C5B—H53B | 109.5 |
H31A—C3A—H32A | 109.5 | H51B—C5B—H53B | 109.5 |
C2A—C3A—H33A | 109.5 | H52B—C5B—H53B | 109.5 |
H31A—C3A—H33A | 109.5 | O1B—C6B—N2B | 124.1 (3) |
H32A—C3A—H33A | 109.5 | O1B—C6B—C1B | 119.6 (2) |
C5A—C4A—C2A | 113.3 (3) | N2B—C6B—C1B | 116.4 (2) |
C5A—C4A—H41A | 108.9 | N2B—C7B—C12B | 107.8 (2) |
C2A—C4A—H41A | 108.9 | N2B—C7B—C8B | 111.7 (2) |
C5A—C4A—H42A | 108.9 | C12B—C7B—C8B | 110.0 (2) |
C2A—C4A—H42A | 108.9 | N2B—C7B—H71B | 109.1 |
H41A—C4A—H42A | 107.7 | C12B—C7B—H71B | 109.1 |
C4A—C5A—H51A | 109.5 | C8B—C7B—H71B | 109.1 |
C4A—C5A—H52A | 109.5 | C9B—C8B—C10B | 111.9 (3) |
H51A—C5A—H52A | 109.5 | C9B—C8B—C7B | 110.1 (2) |
C4A—C5A—H53A | 109.5 | C10B—C8B—C7B | 112.3 (3) |
H51A—C5A—H53A | 109.5 | C9B—C8B—H81B | 107.4 |
H52A—C5A—H53A | 109.5 | C10B—C8B—H81B | 107.4 |
O1A—C6A—N2A | 124.1 (3) | C7B—C8B—H81B | 107.4 |
O1A—C6A—C1A | 119.3 (3) | C8B—C9B—H91B | 109.5 |
N2A—C6A—C1A | 116.6 (2) | C8B—C9B—H92B | 109.5 |
N2A—C7A—C12A | 108.1 (2) | H91B—C9B—H92B | 109.5 |
N2A—C7A—C8A | 111.1 (2) | C8B—C9B—H93B | 109.5 |
C12A—C7A—C8A | 110.3 (2) | H91B—C9B—H93B | 109.5 |
N2A—C7A—H71A | 109.1 | H92B—C9B—H93B | 109.5 |
C12A—C7A—H71A | 109.1 | C11B—C10B—C8B | 113.1 (3) |
C8A—C7A—H71A | 109.1 | C11B—C10B—H12B | 109.0 |
C10A—C8A—C9A | 111.1 (3) | C8B—C10B—H12B | 109.0 |
C10A—C8A—C7A | 111.3 (2) | C11B—C10B—H13B | 109.0 |
C9A—C8A—C7A | 110.6 (2) | C8B—C10B—H13B | 109.0 |
C10A—C8A—H81A | 107.9 | H12B—C10B—H13B | 107.8 |
C9A—C8A—H81A | 107.9 | C10B—C11B—H14B | 109.5 |
C7A—C8A—H81A | 107.9 | C10B—C11B—H15B | 109.5 |
C8A—C9A—H91A | 109.5 | H14B—C11B—H15B | 109.5 |
C8A—C9A—H92A | 109.5 | C10B—C11B—H16B | 109.5 |
H91A—C9A—H92A | 109.5 | H14B—C11B—H16B | 109.5 |
C8A—C9A—H93A | 109.5 | H15B—C11B—H16B | 109.5 |
H91A—C9A—H93A | 109.5 | O2B—C12B—O3B | 121.4 (3) |
H92A—C9A—H93A | 109.5 | O2B—C12B—C7B | 118.2 (3) |
C8A—C10A—C11A | 113.5 (3) | O3B—C12B—C7B | 120.4 (2) |
C8A—C10A—H12A | 108.9 | O2C—N1C—O3C | 119.4 (7) |
C11A—C10A—H12A | 108.9 | O2C—N1C—O1C | 124.9 (5) |
C8A—C10A—H13A | 108.9 | O3C—N1C—O1C | 115.7 (8) |
C11A—C10A—H13A | 108.9 | O5C—N2C—O6C | 119.3 (7) |
H12A—C10A—H13A | 107.7 | O5C—N2C—O4C | 125.1 (6) |
C10A—C11A—H14A | 109.5 | O6C—N2C—O4C | 115.7 (8) |
C10A—C11A—H15A | 109.5 | O2D—N1D—O3D | 119.3 (8) |
H14A—C11A—H15A | 109.5 | O2D—N1D—O1D | 124.9 (6) |
C10A—C11A—H16A | 109.5 | O3D—N1D—O1D | 115.8 (9) |
H14A—C11A—H16A | 109.5 | O8C—N3C—O9C | 119.2 (8) |
H15A—C11A—H16A | 109.5 | O8C—N3C—O7C | 124.7 (6) |
O2A—C12A—O3A | 121.7 (3) | O9C—N3C—O7C | 115.7 (10) |
O2A—C12A—C7A | 118.6 (3) | N1E—C1E—C2E | 176.6 (6) |
O3A—C12A—C7A | 119.6 (2) | N1F—C1F—C2F | 178.0 (12) |
C12B—O3B—H5B | 117.7 (18) | N1F—C1F—C2Fi | 165.6 (10) |
C1B—N1B—H1B | 109.5 | C2F—C1F—C2Fi | 12.7 (6) |
C1B—N1B—H2B | 109.5 | N1G—C1G—C1Gi | 124.5 (10) |
H1B—N1B—H2B | 109.5 | N1G—C1G—C2G | 165.7 (17) |
C1B—N1B—H3B | 109.5 | C1Gi—C1G—C2G | 65.8 (12) |
H1B—N1B—H3B | 109.5 | N1G—C1G—C2Gi | 166 (2) |
H2B—N1B—H3B | 109.5 | C1Gi—C1G—C2Gi | 60.7 (10) |
C6B—N2B—C7B | 122.7 (2) | C2G—C1G—C2Gi | 24.0 (19) |
C6B—N2B—H4B | 118.6 | C1G—C2G—H1G | 109.5 |
C7B—N2B—H4B | 118.7 | C1G—C2G—H2G | 109.5 |
N1B—C1B—C6B | 105.2 (2) | H1G—C2G—H2G | 109.5 |
N1B—C1B—C2B | 112.4 (2) | C1G—C2G—H3G | 109.5 |
C6B—C1B—C2B | 110.0 (2) | H1G—C2G—H3G | 109.5 |
N1B—C1B—H11B | 109.7 | H2G—C2G—H3G | 109.5 |
| | | |
N1A—C1A—C2A—C3A | 175.1 (3) | N1B—C1B—C2B—C3B | 176.6 (2) |
C6A—C1A—C2A—C3A | 59.1 (3) | C6B—C1B—C2B—C3B | 59.6 (3) |
N1A—C1A—C2A—C4A | −60.9 (3) | N1B—C1B—C2B—C4B | −59.3 (3) |
C6A—C1A—C2A—C4A | −177.0 (3) | C6B—C1B—C2B—C4B | −176.2 (2) |
C3A—C2A—C4A—C5A | −72.7 (4) | C3B—C2B—C4B—C5B | −66.8 (4) |
C1A—C2A—C4A—C5A | 164.7 (3) | C1B—C2B—C4B—C5B | 169.8 (3) |
C7A—N2A—C6A—O1A | 4.5 (5) | C7B—N2B—C6B—O1B | −2.1 (4) |
C7A—N2A—C6A—C1A | −173.7 (2) | C7B—N2B—C6B—C1B | 178.6 (2) |
N1A—C1A—C6A—O1A | −57.5 (3) | N1B—C1B—C6B—O1B | −50.9 (3) |
C2A—C1A—C6A—O1A | 63.0 (4) | C2B—C1B—C6B—O1B | 70.4 (3) |
N1A—C1A—C6A—N2A | 120.7 (3) | N1B—C1B—C6B—N2B | 128.5 (2) |
C2A—C1A—C6A—N2A | −118.8 (3) | C2B—C1B—C6B—N2B | −110.2 (3) |
C6A—N2A—C7A—C12A | −133.1 (3) | C6B—N2B—C7B—C12B | −131.2 (3) |
C6A—N2A—C7A—C8A | 105.7 (3) | C6B—N2B—C7B—C8B | 107.8 (3) |
N2A—C7A—C8A—C10A | −63.1 (3) | N2B—C7B—C8B—C9B | 176.4 (2) |
C12A—C7A—C8A—C10A | 177.0 (2) | C12B—C7B—C8B—C9B | 56.7 (3) |
N2A—C7A—C8A—C9A | 172.9 (2) | N2B—C7B—C8B—C10B | −58.2 (3) |
C12A—C7A—C8A—C9A | 52.9 (3) | C12B—C7B—C8B—C10B | −178.0 (2) |
C9A—C8A—C10A—C11A | −71.2 (4) | C9B—C8B—C10B—C11B | −70.6 (4) |
C7A—C8A—C10A—C11A | 165.0 (3) | C7B—C8B—C10B—C11B | 165.0 (3) |
N2A—C7A—C12A—O2A | −51.8 (4) | N2B—C7B—C12B—O2B | −52.9 (3) |
C8A—C7A—C12A—O2A | 69.9 (3) | C8B—C7B—C12B—O2B | 69.2 (3) |
N2A—C7A—C12A—O3A | 131.5 (3) | N2B—C7B—C12B—O3B | 129.4 (3) |
C8A—C7A—C12A—O3A | −106.8 (3) | C8B—C7B—C12B—O3B | −108.5 (3) |
Symmetry code: (i) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3B—H5B···O3A | 1.12 (3) | 1.31 (3) | 2.429 (3) | 173 (3) |
N1A—H1A···N1Eii | 0.89 | 2.23 | 2.952 (5) | 138 |
N1A—H1A···O2Ciii | 0.89 | 2.24 | 2.745 (7) | 115 |
N1A—H2A···O2Aii | 0.89 | 2.00 | 2.841 (3) | 156 |
N1A—H2A···O3Aii | 0.89 | 2.47 | 3.188 (3) | 139 |
N1A—H3A···O2Biii | 0.89 | 2.02 | 2.843 (3) | 154 |
N2A—H4A···O1Bii | 0.86 | 2.21 | 3.033 (3) | 161 |
C1A—H11A···O1Bii | 0.98 | 2.36 | 3.244 (3) | 150 |
N1B—H1B···O3Civ | 0.89 | 1.90 | 2.782 (15) | 173 |
N1B—H1B···O1Div | 0.89 | 2.20 | 2.88 (3) | 133 |
N1B—H2B···O2Biv | 0.89 | 2.02 | 2.865 (3) | 158 |
N1B—H2B···O3Biv | 0.89 | 2.50 | 3.223 (3) | 139 |
N1B—H3B···O2Av | 0.89 | 2.00 | 2.828 (3) | 155 |
N2B—H4B···O1Aiv | 0.86 | 2.16 | 2.989 (3) | 162 |
C1B—H11B···O1Aiv | 0.98 | 2.33 | 3.215 (3) | 150 |
C2F—H3F···O1C | 0.96 | 1.91 | 2.827 (3) | 158 |
Symmetry codes: (ii) x+1/2, −y+3/2, −z; (iii) x+1/2, −y+3/2, −z+1; (iv) x−1/2, −y+3/2, −z+1; (v) x−1/2, −y+3/2, −z. |
(IIz)
L-Isoleucyl-
L-isoleucine dihydrate
top
Crystal data top
C12H28N2O5 | Dx = 1.187 Mg m−3 |
Mr = 280.36 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 14734 reflections |
a = 7.6341 (3) Å | θ = 2.1–35.0° |
b = 12.5335 (6) Å | µ = 0.09 mm−1 |
c = 16.3923 (7) Å | T = 105 K |
V = 1568.45 (12) Å3 | Block, colourless |
Z = 4 | 1.10 × 0.45 × 0.25 mm |
F(000) = 616 | |
Data collection top
Siemens SMART CCD diffractometer | 6861 independent reflections |
Radiation source: fine-focus sealed tube | 6294 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.3 pixels mm-1 | θmax = 35.0°, θmin = 2.1° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −12→12 |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | k = −19→20 |
Tmin = 0.848, Tmax = 0.978 | l = −26→26 |
21646 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0556P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6861 reflections | Δρmax = 0.32 e Å−3 |
210 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (4) |
Crystal data top
C12H28N2O5 | V = 1568.45 (12) Å3 |
Mr = 280.36 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.6341 (3) Å | µ = 0.09 mm−1 |
b = 12.5335 (6) Å | T = 105 K |
c = 16.3923 (7) Å | 1.10 × 0.45 × 0.25 mm |
Data collection top
Siemens SMART CCD diffractometer | 6861 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | 6294 reflections with I > 2σ(I) |
Tmin = 0.848, Tmax = 0.978 | Rint = 0.022 |
21646 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | Δρmax = 0.32 e Å−3 |
S = 1.05 | Δρmin = −0.16 e Å−3 |
6861 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
210 parameters | Absolute structure parameter: −0.2 (4) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.18949 (6) | 0.31325 (5) | 0.13844 (4) | 0.02743 (11) | |
O2 | −0.14950 (6) | 0.59732 (4) | 0.32756 (4) | 0.02499 (11) | |
O3 | −0.43548 (6) | 0.56597 (4) | 0.34837 (3) | 0.02264 (10) | |
N1 | 0.15324 (7) | 0.28687 (4) | 0.09050 (3) | 0.01639 (9) | |
H1 | 0.1437 (14) | 0.2271 (9) | 0.1236 (6) | 0.025* | |
H2 | 0.2598 (15) | 0.2909 (9) | 0.0796 (6) | 0.025* | |
H3 | 0.0938 (14) | 0.2774 (9) | 0.0435 (6) | 0.025* | |
N2 | −0.10005 (6) | 0.42103 (4) | 0.24256 (3) | 0.01724 (9) | |
H4 | −0.0199 (13) | 0.4565 (9) | 0.2636 (6) | 0.021* | |
C1 | 0.09904 (7) | 0.38781 (4) | 0.13158 (3) | 0.01466 (9) | |
H11 | 0.1826 (9) | 0.40556 (19) | 0.1719 (4) | 0.018* | |
C2 | 0.09039 (8) | 0.47867 (5) | 0.06779 (4) | 0.01819 (10) | |
H21 | 0.0151 (8) | 0.4552 (3) | 0.0244 (5) | 0.022* | |
C3 | 0.01044 (10) | 0.58070 (5) | 0.10372 (5) | 0.02514 (13) | |
H31 | −0.1114 (10) | 0.56710 (19) | 0.1194 (4) | 0.038* | |
H32 | 0.0140 (8) | 0.6377 (5) | 0.0628 (3) | 0.038* | |
H33 | 0.0776 (7) | 0.6025 (3) | 0.1519 (4) | 0.038* | |
C4 | 0.27317 (9) | 0.49941 (6) | 0.03070 (4) | 0.02484 (13) | |
H41 | 0.3073 (3) | 0.4374 (5) | −0.0010 (3) | 0.030* | |
H42 | 0.26484 (12) | 0.5594 (5) | −0.0065 (3) | 0.030* | |
C5 | 0.41688 (10) | 0.52274 (7) | 0.09295 (5) | 0.02961 (15) | |
H51 | 0.5233 (9) | 0.5503 (7) | 0.0641 (2) | 0.044* | |
H52 | 0.4472 (8) | 0.4556 (5) | 0.1229 (4) | 0.044* | |
H53 | 0.3744 (5) | 0.5776 (6) | 0.1327 (4) | 0.044* | |
C6 | −0.07799 (7) | 0.36975 (5) | 0.17218 (4) | 0.01611 (10) | |
C7 | −0.26939 (7) | 0.42941 (5) | 0.28367 (4) | 0.01535 (9) | |
H71 | −0.3582 (9) | 0.42214 (9) | 0.2444 (4) | 0.018* | |
C8 | −0.29109 (8) | 0.33920 (5) | 0.34763 (4) | 0.01819 (10) | |
H81 | −0.2492 (5) | 0.2747 (8) | 0.3231 (3) | 0.022* | |
C9 | −0.17735 (11) | 0.36074 (7) | 0.42257 (5) | 0.02926 (15) | |
H91 | −0.1844 (9) | 0.3008 (6) | 0.4594 (4) | 0.044* | |
H92 | −0.2185 (8) | 0.4242 (6) | 0.4498 (4) | 0.044* | |
H93 | −0.0573 (10) | 0.3708 (7) | 0.40578 (16) | 0.044* | |
C10 | −0.48263 (9) | 0.31989 (6) | 0.37261 (4) | 0.02383 (12) | |
H101 | −0.48484 (10) | 0.2680 (4) | 0.4173 (4) | 0.029* | |
H102 | −0.5315 (4) | 0.3868 (6) | 0.39343 (19) | 0.029* | |
C11 | −0.59937 (10) | 0.27942 (7) | 0.30414 (5) | 0.03235 (15) | |
H111 | −0.7120 (10) | 0.2635 (7) | 0.3252 (2) | 0.049* | |
H112 | −0.5497 (7) | 0.2169 (6) | 0.2813 (4) | 0.049* | |
H113 | −0.6092 (9) | 0.3326 (5) | 0.2633 (4) | 0.049* | |
C12 | −0.28492 (8) | 0.54105 (5) | 0.32253 (4) | 0.01738 (10) | |
O1W | 0.78097 (7) | 0.04139 (6) | 0.20519 (4) | 0.03645 (15) | |
H11W | 0.686 (2) | 0.0479 (13) | 0.1831 (9) | 0.055* | |
H12W | 0.841 (2) | 0.0854 (13) | 0.1836 (10) | 0.055* | |
O2W | 0.50836 (6) | 0.24232 (4) | 0.06819 (3) | 0.01836 (8) | |
H21W | 0.5848 (16) | 0.2646 (10) | 0.0939 (7) | 0.028* | |
H22W | 0.4767 (15) | 0.1866 (10) | 0.0962 (7) | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.01726 (19) | 0.0338 (3) | 0.0312 (3) | −0.00742 (19) | 0.00188 (18) | −0.0152 (2) |
O2 | 0.0208 (2) | 0.0186 (2) | 0.0355 (3) | −0.00283 (16) | 0.00355 (18) | −0.00871 (19) |
O3 | 0.01754 (18) | 0.01755 (19) | 0.0328 (2) | 0.00288 (15) | 0.00169 (17) | −0.00418 (18) |
N1 | 0.01476 (19) | 0.0150 (2) | 0.0194 (2) | 0.00098 (16) | 0.00065 (16) | 0.00038 (17) |
N2 | 0.01460 (18) | 0.0186 (2) | 0.0185 (2) | −0.00224 (16) | 0.00014 (16) | −0.00404 (17) |
C1 | 0.01430 (19) | 0.0139 (2) | 0.0158 (2) | −0.00096 (17) | −0.00064 (17) | −0.00055 (17) |
C2 | 0.0215 (2) | 0.0153 (2) | 0.0178 (2) | −0.0004 (2) | −0.0027 (2) | 0.00175 (19) |
C3 | 0.0336 (3) | 0.0147 (3) | 0.0271 (3) | 0.0022 (2) | −0.0025 (3) | 0.0015 (2) |
C4 | 0.0269 (3) | 0.0261 (3) | 0.0215 (3) | −0.0033 (2) | 0.0026 (2) | 0.0067 (2) |
C5 | 0.0235 (3) | 0.0321 (4) | 0.0332 (3) | −0.0088 (3) | 0.0005 (3) | 0.0065 (3) |
C6 | 0.01441 (19) | 0.0152 (2) | 0.0187 (2) | −0.00094 (18) | −0.00023 (18) | −0.00143 (19) |
C7 | 0.01466 (19) | 0.0148 (2) | 0.0166 (2) | 0.00010 (18) | −0.00051 (17) | −0.00140 (18) |
C8 | 0.0221 (2) | 0.0152 (2) | 0.0173 (2) | 0.00249 (19) | −0.0004 (2) | −0.00053 (19) |
C9 | 0.0369 (3) | 0.0296 (3) | 0.0213 (3) | 0.0060 (3) | −0.0098 (3) | 0.0001 (3) |
C10 | 0.0282 (3) | 0.0191 (3) | 0.0242 (3) | −0.0018 (2) | 0.0083 (2) | 0.0001 (2) |
C11 | 0.0265 (3) | 0.0320 (4) | 0.0385 (4) | −0.0078 (3) | −0.0011 (3) | 0.0047 (3) |
C12 | 0.0182 (2) | 0.0146 (2) | 0.0194 (2) | 0.00158 (18) | −0.00108 (18) | −0.00134 (19) |
O1W | 0.0197 (2) | 0.0466 (4) | 0.0430 (3) | −0.0021 (2) | −0.0063 (2) | 0.0209 (3) |
O2W | 0.01626 (17) | 0.0180 (2) | 0.0208 (2) | −0.00309 (15) | −0.00210 (15) | −0.00033 (16) |
Geometric parameters (Å, º) top
O1—C6 | 1.2377 (7) | C5—H51 | 1.0012 |
O2—C12 | 1.2542 (8) | C5—H52 | 1.0012 |
O3—C12 | 1.2641 (7) | C5—H53 | 1.0012 |
N1—C1 | 1.4918 (8) | C7—C12 | 1.5420 (8) |
N1—H1 | 0.928 (11) | C7—C8 | 1.5509 (8) |
N1—H2 | 0.835 (11) | C7—H71 | 0.9398 |
N1—H3 | 0.903 (10) | C8—C9 | 1.5283 (10) |
N2—C6 | 1.3314 (8) | C8—C10 | 1.5377 (9) |
N2—C7 | 1.4616 (7) | C8—H81 | 0.9583 |
N2—H4 | 0.831 (11) | C9—H91 | 0.9650 |
C1—C6 | 1.5233 (8) | C9—H92 | 0.9650 |
C1—C2 | 1.5474 (8) | C9—H93 | 0.9650 |
C1—H11 | 0.9448 | C10—C11 | 1.5202 (11) |
C2—C3 | 1.5345 (9) | C10—H101 | 0.9796 |
C2—C4 | 1.5441 (9) | C10—H102 | 0.9796 |
C2—H21 | 0.9606 | C11—H111 | 0.9476 |
C3—H31 | 0.9799 | C11—H112 | 0.9476 |
C3—H32 | 0.9799 | C11—H113 | 0.9476 |
C3—H33 | 0.9799 | O1W—H11W | 0.811 (16) |
C4—C5 | 1.5266 (11) | O1W—H12W | 0.801 (17) |
C4—H41 | 0.9703 | O2W—H21W | 0.772 (12) |
C4—H42 | 0.9703 | O2W—H22W | 0.870 (12) |
| | | |
C1—N1—H1 | 113.5 (7) | O1—C6—N2 | 125.20 (6) |
C1—N1—H2 | 108.5 (8) | O1—C6—C1 | 120.00 (5) |
H1—N1—H2 | 104.5 (10) | N2—C6—C1 | 114.78 (5) |
C1—N1—H3 | 110.9 (7) | N2—C7—C12 | 108.89 (5) |
H1—N1—H3 | 110.8 (10) | N2—C7—C8 | 110.72 (5) |
H2—N1—H3 | 108.3 (10) | C12—C7—C8 | 111.97 (5) |
C6—N2—C7 | 123.10 (5) | N2—C7—H71 | 108.4 |
C6—N2—H4 | 121.6 (7) | C12—C7—H71 | 108.4 |
C7—N2—H4 | 115.0 (7) | C8—C7—H71 | 108.4 |
N1—C1—C6 | 108.50 (4) | C9—C8—C10 | 110.74 (6) |
N1—C1—C2 | 109.32 (5) | C9—C8—C7 | 110.73 (5) |
C6—C1—C2 | 111.51 (5) | C10—C8—C7 | 113.35 (5) |
N1—C1—H11 | 109.2 | C9—C8—H81 | 107.2 |
C6—C1—H11 | 109.2 | C10—C8—H81 | 107.2 |
C2—C1—H11 | 109.2 | C7—C8—H81 | 107.2 |
C3—C2—C4 | 111.73 (6) | C8—C9—H91 | 109.5 |
C3—C2—C1 | 111.77 (5) | C8—C9—H92 | 109.5 |
C4—C2—C1 | 110.58 (5) | H91—C9—H92 | 109.5 |
C3—C2—H21 | 107.5 | C8—C9—H93 | 109.5 |
C4—C2—H21 | 107.5 | H91—C9—H93 | 109.5 |
C1—C2—H21 | 107.5 | H92—C9—H93 | 109.5 |
C2—C3—H31 | 109.5 | C11—C10—C8 | 114.42 (6) |
C2—C3—H32 | 109.5 | C11—C10—H101 | 108.7 |
H31—C3—H32 | 109.5 | C8—C10—H101 | 108.7 |
C2—C3—H33 | 109.5 | C11—C10—H102 | 108.7 |
H31—C3—H33 | 109.5 | C8—C10—H102 | 108.7 |
H32—C3—H33 | 109.5 | H101—C10—H102 | 107.6 |
C5—C4—C2 | 114.73 (6) | C10—C11—H111 | 109.5 |
C5—C4—H41 | 108.6 | C10—C11—H112 | 109.5 |
C2—C4—H41 | 108.6 | H111—C11—H112 | 109.5 |
C5—C4—H42 | 108.6 | C10—C11—H113 | 109.5 |
C2—C4—H42 | 108.6 | H111—C11—H113 | 109.5 |
H41—C4—H42 | 107.6 | H112—C11—H113 | 109.5 |
C4—C5—H51 | 109.5 | O2—C12—O3 | 126.05 (6) |
C4—C5—H52 | 109.5 | O2—C12—C7 | 118.30 (5) |
H51—C5—H52 | 109.5 | O3—C12—C7 | 115.63 (5) |
C4—C5—H53 | 109.5 | H11W—O1W—H12W | 104.3 (15) |
H51—C5—H53 | 109.5 | H21W—O2W—H22W | 102.2 (11) |
H52—C5—H53 | 109.5 | | |
| | | |
N1—C1—C2—C3 | 171.90 (5) | C6—N2—C7—C12 | −142.51 (6) |
C6—C1—C2—C3 | 51.93 (6) | C6—N2—C7—C8 | 93.98 (7) |
N1—C1—C2—C4 | −62.94 (6) | N2—C7—C8—C9 | 73.77 (6) |
C6—C1—C2—C4 | 177.09 (5) | C12—C7—C8—C9 | −47.94 (7) |
C3—C2—C4—C5 | 70.24 (8) | N2—C7—C8—C10 | −161.08 (5) |
C1—C2—C4—C5 | −54.94 (8) | C12—C7—C8—C10 | 77.21 (6) |
C7—N2—C6—O1 | −9.11 (10) | C9—C8—C10—C11 | −170.15 (6) |
C7—N2—C6—C1 | 168.96 (5) | C7—C8—C10—C11 | 64.71 (7) |
N1—C1—C6—O1 | −37.12 (8) | N2—C7—C12—O2 | −12.99 (8) |
C2—C1—C6—O1 | 83.33 (7) | C8—C7—C12—O2 | 109.77 (6) |
N1—C1—C6—N2 | 144.70 (5) | N2—C7—C12—O3 | 168.66 (5) |
C2—C1—C6—N2 | −94.85 (6) | C8—C7—C12—O3 | −68.58 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.928 (11) | 1.814 (11) | 2.7293 (7) | 168.7 (10) |
N1—H2···O2w | 0.835 (11) | 2.001 (12) | 2.7920 (7) | 157.8 (11) |
N1—H3···O2Wii | 0.903 (10) | 1.959 (10) | 2.8502 (7) | 169.2 (10) |
N2—H4···O1Wiii | 0.831 (11) | 2.173 (11) | 2.9905 (8) | 167.9 (9) |
O1W—H11W···O3i | 0.811 (16) | 1.997 (16) | 2.7968 (7) | 168.5 (15) |
O1W—H12W···O2iv | 0.801 (17) | 2.364 (15) | 2.9487 (8) | 130.6 (14) |
O2W—H21W···O1v | 0.772 (12) | 1.969 (13) | 2.7271 (7) | 167.5 (12) |
O2W—H22W···O3i | 0.870 (12) | 1.792 (13) | 2.6582 (7) | 173.6 (11) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, −z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x+1, y, z. |
(IIa) Ammonium
L-Leucyl-
L-Leucinate
top
Crystal data top
C12H27N3O3 | Z = 2 |
Mr = 261.37 | F(000) = 288 |
Triclinic, P1 | Dx = 1.137 Mg m−3 |
a = 6.7765 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.718 (2) Å | Cell parameters from 2001 reflections |
c = 11.882 (3) Å | θ = 2.1–26.4° |
α = 81.580 (3)° | µ = 0.08 mm−1 |
β = 80.484 (3)° | T = 105 K |
γ = 88.350 (3)° | Block, colourless |
V = 763.4 (3) Å3 | 0.55 × 0.24 × 0.22 mm |
Data collection top
Siemens SMART CCD diffractometer | 3063 independent reflections |
Radiation source: fine-focus sealed tube | 2165 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 8.3 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −8→8 |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | k = −11→12 |
Tmin = 0.779, Tmax = 0.982 | l = −14→14 |
6449 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.005 |
3063 reflections | Δρmax = 0.32 e Å−3 |
395 parameters | Δρmin = −0.23 e Å−3 |
11 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.7 (14) |
Crystal data top
C12H27N3O3 | γ = 88.350 (3)° |
Mr = 261.37 | V = 763.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7765 (15) Å | Mo Kα radiation |
b = 9.718 (2) Å | µ = 0.08 mm−1 |
c = 11.882 (3) Å | T = 105 K |
α = 81.580 (3)° | 0.55 × 0.24 × 0.22 mm |
β = 80.484 (3)° | |
Data collection top
Siemens SMART CCD diffractometer | 3063 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996) | 2165 reflections with I > 2σ(I) |
Tmin = 0.779, Tmax = 0.982 | Rint = 0.045 |
6449 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | Δρmax = 0.32 e Å−3 |
S = 0.98 | Δρmin = −0.23 e Å−3 |
3063 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
395 parameters | Absolute structure parameter: −0.7 (14) |
11 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.5836 (4) | 0.3982 (3) | 0.6181 (2) | 0.0269 (6) | |
O2A | 0.7905 (4) | 0.8472 (3) | 0.6621 (2) | 0.0277 (6) | |
O3A | 0.5084 (4) | 0.9027 (3) | 0.5900 (2) | 0.0288 (7) | |
N1A | 1.0889 (5) | 0.4805 (4) | 0.6284 (3) | 0.0269 (8) | |
H1A | 1.103 (7) | 0.531 (5) | 0.555 (4) | 0.040* | |
H2A | 1.206 (7) | 0.443 (5) | 0.639 (4) | 0.040* | |
N2A | 0.7137 (5) | 0.5758 (3) | 0.6874 (3) | 0.0233 (7) | |
H4A | 0.824 (7) | 0.613 (4) | 0.691 (3) | 0.028* | |
C1A | 0.9288 (5) | 0.3754 (4) | 0.6519 (3) | 0.0228 (9) | |
H11A | 0.9511 (10) | 0.310 (3) | 0.585 (3) | 0.027* | |
C2A | 0.9368 (6) | 0.2845 (4) | 0.7702 (4) | 0.0311 (10) | |
H21A | 0.9466 (8) | 0.344 (3) | 0.824 (3) | 0.037* | |
C3A | 0.7488 (7) | 0.1952 (5) | 0.8139 (4) | 0.0394 (11) | |
H31A | 0.627 (4) | 0.2567 (18) | 0.817 (2) | 0.059* | |
H32A | 0.756 (2) | 0.145 (3) | 0.893 (2) | 0.059* | |
H33A | 0.740 (2) | 0.126 (3) | 0.760 (2) | 0.059* | |
C4A | 1.1300 (7) | 0.1904 (6) | 0.7605 (5) | 0.0564 (15) | |
H41A | 1.1137 (8) | 0.117 (3) | 0.708 (2) | 0.068* | |
H42A | 1.251 (5) | 0.252 (2) | 0.7209 (16) | 0.068* | |
C5A | 1.1752 (9) | 0.1163 (6) | 0.8742 (5) | 0.0603 (15) | |
H51A | 1.322 (5) | 0.048 (3) | 0.8579 (7) | 0.090* | |
H52A | 1.040 (4) | 0.043 (3) | 0.920 (2) | 0.090* | |
H53A | 1.200 (5) | 0.199 (2) | 0.934 (2) | 0.090* | |
C6A | 0.7265 (5) | 0.4512 (4) | 0.6511 (3) | 0.0228 (9) | |
C7A | 0.5416 (6) | 0.6692 (4) | 0.6856 (3) | 0.0229 (9) | |
H71A | 0.467 (3) | 0.6445 (12) | 0.632 (2) | 0.027* | |
C8A | 0.4034 (5) | 0.6575 (4) | 0.8042 (3) | 0.0230 (9) | |
H81A | 0.3587 (17) | 0.552 (4) | 0.8273 (9) | 0.028* | |
C9A | 0.5161 (6) | 0.6937 (5) | 0.8987 (4) | 0.0339 (10) | |
H91A | 0.426 (3) | 0.678 (3) | 0.975 (2) | 0.051* | |
H92A | 0.557 (4) | 0.794 (3) | 0.8809 (13) | 0.051* | |
H93A | 0.638 (4) | 0.633 (2) | 0.9013 (16) | 0.051* | |
C10A | 0.2133 (6) | 0.7451 (4) | 0.7979 (4) | 0.0269 (9) | |
H12A | 0.2515 (12) | 0.846 (3) | 0.7797 (7) | 0.032* | |
H13A | 0.150 (2) | 0.7214 (8) | 0.733 (2) | 0.032* | |
C11A | 0.0593 (7) | 0.7251 (5) | 0.9080 (4) | 0.0405 (12) | |
H14A | −0.060 (4) | 0.782 (3) | 0.8962 (10) | 0.061* | |
H15A | 0.117 (2) | 0.754 (3) | 0.971 (2) | 0.061* | |
H16A | 0.022 (4) | 0.627 (3) | 0.9273 (16) | 0.061* | |
C12A | 0.6197 (5) | 0.8182 (4) | 0.6423 (3) | 0.0219 (9) | |
O1B | 0.1411 (4) | 0.6810 (3) | 0.3736 (2) | 0.0256 (6) | |
O2B | 0.3897 (4) | 0.2238 (3) | 0.3336 (2) | 0.0257 (6) | |
O3B | 0.0690 (4) | 0.1764 (3) | 0.4097 (2) | 0.0254 (6) | |
N1B | 0.6565 (5) | 0.5926 (3) | 0.3610 (3) | 0.0256 (8) | |
H1B | 0.620 (7) | 0.560 (5) | 0.439 (4) | 0.038* | |
H2B | 0.759 (7) | 0.642 (5) | 0.356 (4) | 0.038* | |
N2B | 0.3177 (5) | 0.4984 (3) | 0.3075 (3) | 0.0246 (8) | |
H4B | 0.422 (7) | 0.476 (5) | 0.296 (4) | 0.029* | |
C1B | 0.5046 (5) | 0.6980 (4) | 0.3318 (3) | 0.0216 (9) | |
H11B | 0.4888 (8) | 0.768 (3) | 0.390 (2) | 0.026* | |
C2B | 0.5699 (6) | 0.7771 (4) | 0.2089 (3) | 0.0247 (9) | |
H21B | 0.5806 (7) | 0.708 (3) | 0.155 (2) | 0.030* | |
C3B | 0.4130 (6) | 0.8857 (4) | 0.1750 (4) | 0.0341 (10) | |
H31B | 0.461 (2) | 0.936 (2) | 0.094 (2) | 0.051* | |
H32B | 0.393 (3) | 0.956 (2) | 0.231 (2) | 0.051* | |
H33B | 0.282 (4) | 0.8376 (13) | 0.177 (2) | 0.051* | |
C4B | 0.7794 (6) | 0.8438 (4) | 0.1959 (4) | 0.0309 (10) | |
H41B | 0.880 (3) | 0.768 (2) | 0.2040 (4) | 0.037* | |
H42B | 0.8127 (12) | 0.8962 (15) | 0.117 (2) | 0.037* | |
C5B | 0.7962 (6) | 0.9417 (4) | 0.2828 (4) | 0.0376 (11) | |
H51B | 0.935 (4) | 0.982 (3) | 0.2677 (16) | 0.056* | |
H52B | 0.769 (4) | 0.8887 (15) | 0.363 (2) | 0.056* | |
H53B | 0.695 (4) | 1.019 (3) | 0.2751 (17) | 0.056* | |
C6B | 0.3049 (6) | 0.6243 (4) | 0.3399 (3) | 0.0216 (9) | |
C7B | 0.1450 (5) | 0.4066 (4) | 0.3120 (3) | 0.0210 (8) | |
H71B | 0.031 (4) | 0.4360 (12) | 0.369 (2) | 0.025* | |
C8B | 0.0755 (5) | 0.4191 (4) | 0.1928 (3) | 0.0229 (9) | |
H81B | 0.0384 (17) | 0.517 (4) | 0.1718 (10) | 0.027* | |
C9B | 0.2417 (6) | 0.3835 (5) | 0.0985 (4) | 0.0327 (10) | |
H91B | 0.1978 (19) | 0.404 (3) | 0.025 (2) | 0.049* | |
H92B | 0.274 (3) | 0.286 (3) | 0.1127 (14) | 0.049* | |
H93B | 0.359 (3) | 0.437 (3) | 0.0984 (16) | 0.049* | |
C10B | −0.1134 (6) | 0.3316 (4) | 0.2020 (3) | 0.0253 (9) | |
H12B | −0.0752 (11) | 0.228 (3) | 0.2155 (6) | 0.030* | |
H13B | −0.214 (3) | 0.3521 (7) | 0.273 (2) | 0.030* | |
C11B | −0.2151 (6) | 0.3585 (5) | 0.0962 (4) | 0.0393 (11) | |
H14B | −0.336 (4) | 0.301 (3) | 0.1088 (11) | 0.059* | |
H15B | −0.123 (3) | 0.335 (3) | 0.029 (2) | 0.059* | |
H16B | −0.252 (4) | 0.457 (3) | 0.0825 (15) | 0.059* | |
C12B | 0.2064 (5) | 0.2561 (4) | 0.3558 (3) | 0.0215 (8) | |
N1C | 0.6475 (5) | 0.1665 (3) | 0.4928 (3) | 0.0235 (7) | |
H1C | 0.626 (6) | 0.231 (3) | 0.536 (3) | 0.035* | |
H2C | 0.572 (6) | 0.186 (4) | 0.438 (3) | 0.035* | |
H3C | 0.614 (6) | 0.086 (3) | 0.533 (3) | 0.035* | |
H4C | 0.768 (4) | 0.185 (5) | 0.463 (4) | 0.035* | |
N1D | 0.1408 (5) | 0.9069 (3) | 0.5061 (3) | 0.0235 (7) | |
H1D | 0.134 (6) | 0.845 (4) | 0.462 (3) | 0.035* | |
H2D | 0.044 (5) | 0.892 (4) | 0.565 (3) | 0.035* | |
H3D | 0.142 (6) | 0.994 (2) | 0.470 (3) | 0.035* | |
H4D | 0.244 (4) | 0.909 (4) | 0.539 (3) | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0209 (15) | 0.0231 (15) | 0.0387 (17) | −0.0027 (12) | −0.0076 (12) | −0.0070 (12) |
O2A | 0.0176 (14) | 0.0267 (15) | 0.0385 (16) | −0.0042 (12) | −0.0036 (12) | −0.0041 (12) |
O3A | 0.0219 (15) | 0.0230 (15) | 0.0410 (17) | −0.0026 (12) | −0.0110 (12) | 0.0042 (12) |
N1A | 0.0206 (19) | 0.026 (2) | 0.035 (2) | −0.0026 (15) | −0.0066 (16) | −0.0040 (16) |
N2A | 0.0142 (16) | 0.0195 (18) | 0.038 (2) | −0.0001 (13) | −0.0065 (14) | −0.0075 (14) |
C1A | 0.017 (2) | 0.022 (2) | 0.030 (2) | −0.0003 (16) | −0.0048 (16) | −0.0048 (17) |
C2A | 0.031 (2) | 0.031 (2) | 0.033 (2) | 0.0003 (18) | −0.0120 (18) | −0.0033 (19) |
C3A | 0.035 (3) | 0.036 (3) | 0.042 (3) | −0.006 (2) | −0.007 (2) | 0.011 (2) |
C4A | 0.034 (3) | 0.056 (3) | 0.074 (4) | −0.003 (3) | −0.023 (3) | 0.025 (3) |
C5A | 0.064 (4) | 0.053 (3) | 0.071 (4) | 0.003 (3) | −0.033 (3) | −0.007 (3) |
C6A | 0.021 (2) | 0.019 (2) | 0.028 (2) | −0.0052 (16) | −0.0022 (16) | −0.0015 (16) |
C7A | 0.021 (2) | 0.019 (2) | 0.030 (2) | 0.0027 (16) | −0.0099 (17) | −0.0060 (16) |
C8A | 0.018 (2) | 0.023 (2) | 0.028 (2) | −0.0052 (16) | −0.0048 (16) | −0.0022 (16) |
C9A | 0.025 (2) | 0.048 (3) | 0.029 (2) | −0.002 (2) | −0.0077 (18) | −0.004 (2) |
C10A | 0.022 (2) | 0.027 (2) | 0.033 (2) | 0.0008 (17) | −0.0052 (17) | −0.0050 (17) |
C11A | 0.027 (2) | 0.049 (3) | 0.043 (3) | 0.003 (2) | −0.002 (2) | −0.001 (2) |
C12A | 0.018 (2) | 0.025 (2) | 0.024 (2) | −0.0012 (17) | −0.0019 (16) | −0.0072 (17) |
O1B | 0.0155 (14) | 0.0199 (15) | 0.0422 (17) | −0.0007 (11) | −0.0041 (12) | −0.0072 (12) |
O2B | 0.0184 (15) | 0.0249 (15) | 0.0342 (15) | 0.0006 (11) | −0.0047 (12) | −0.0053 (12) |
O3B | 0.0169 (14) | 0.0190 (14) | 0.0391 (16) | −0.0024 (11) | −0.0051 (11) | 0.0013 (12) |
N1B | 0.0180 (18) | 0.0204 (19) | 0.038 (2) | −0.0046 (14) | −0.0051 (15) | −0.0018 (16) |
N2B | 0.0172 (17) | 0.0176 (18) | 0.040 (2) | −0.0018 (14) | −0.0060 (15) | −0.0071 (14) |
C1B | 0.018 (2) | 0.019 (2) | 0.028 (2) | −0.0005 (16) | −0.0057 (16) | −0.0054 (16) |
C2B | 0.025 (2) | 0.023 (2) | 0.027 (2) | −0.0033 (16) | −0.0021 (16) | −0.0065 (17) |
C3B | 0.028 (2) | 0.029 (2) | 0.044 (3) | −0.0020 (19) | −0.0127 (19) | 0.0043 (19) |
C4B | 0.022 (2) | 0.027 (2) | 0.042 (3) | −0.0061 (17) | −0.0005 (18) | −0.0029 (19) |
C5B | 0.026 (2) | 0.029 (2) | 0.060 (3) | −0.0074 (19) | −0.005 (2) | −0.013 (2) |
C6B | 0.020 (2) | 0.018 (2) | 0.026 (2) | −0.0052 (16) | −0.0053 (16) | 0.0002 (16) |
C7B | 0.0159 (19) | 0.0161 (19) | 0.031 (2) | −0.0009 (15) | −0.0030 (16) | −0.0042 (16) |
C8B | 0.022 (2) | 0.016 (2) | 0.031 (2) | −0.0004 (16) | −0.0062 (17) | −0.0005 (16) |
C9B | 0.023 (2) | 0.041 (3) | 0.033 (2) | −0.0036 (19) | −0.0052 (18) | 0.0010 (19) |
C10B | 0.022 (2) | 0.023 (2) | 0.033 (2) | −0.0011 (17) | −0.0090 (17) | −0.0047 (17) |
C11B | 0.020 (2) | 0.063 (3) | 0.037 (3) | −0.007 (2) | −0.0124 (19) | −0.002 (2) |
C12B | 0.019 (2) | 0.023 (2) | 0.025 (2) | −0.0037 (17) | −0.0087 (16) | −0.0064 (17) |
N1C | 0.0182 (18) | 0.0195 (19) | 0.034 (2) | −0.0056 (15) | −0.0060 (15) | −0.0038 (15) |
N1D | 0.0197 (18) | 0.0185 (18) | 0.034 (2) | −0.0026 (15) | −0.0065 (15) | −0.0071 (15) |
Geometric parameters (Å, º) top
O1A—C6A | 1.253 (4) | N1B—H1B | 0.93 (5) |
O2A—C12A | 1.266 (4) | N1B—H2B | 0.85 (5) |
O3A—C12A | 1.265 (5) | N2B—C6B | 1.332 (5) |
N1A—C1A | 1.476 (5) | N2B—C7B | 1.481 (5) |
N1A—H1A | 0.93 (5) | N2B—H4B | 0.73 (4) |
N1A—H2A | 0.88 (5) | C1B—C6B | 1.532 (5) |
N2A—C6A | 1.340 (5) | C1B—C2B | 1.549 (5) |
N2A—C7A | 1.458 (5) | C1B—H11B | 1.0291 |
N2A—H4A | 0.85 (4) | C2B—C3B | 1.536 (6) |
C1A—C6A | 1.538 (5) | C2B—C4B | 1.553 (5) |
C1A—C2A | 1.555 (6) | C2B—H21B | 0.9904 |
C1A—H11A | 1.0816 | C3B—H31B | 1.0139 |
C2A—C3A | 1.536 (6) | C3B—H32B | 1.0139 |
C2A—C4A | 1.573 (7) | C3B—H33B | 1.0139 |
C2A—H21A | 0.9309 | C4B—C5B | 1.522 (6) |
C3A—H31A | 1.0048 | C4B—H41B | 0.9935 |
C3A—H32A | 1.0048 | C4B—H42B | 0.9935 |
C3A—H33A | 1.0048 | C5B—H51B | 1.0076 |
C4A—C5A | 1.510 (7) | C5B—H52B | 1.0076 |
C4A—H41A | 1.0329 | C5B—H53B | 1.0076 |
C4A—H42A | 1.0329 | C7B—C12B | 1.548 (5) |
C5A—H51A | 1.1830 | C7B—C8B | 1.552 (5) |
C5A—H52A | 1.1830 | C7B—H71B | 1.0061 |
C5A—H53A | 1.1830 | C8B—C9B | 1.522 (6) |
C7A—C12A | 1.542 (5) | C8B—C10B | 1.537 (5) |
C7A—C8A | 1.549 (5) | C8B—H81B | 0.9810 |
C7A—H71A | 0.9309 | C9B—H91B | 0.9638 |
C8A—C10A | 1.529 (6) | C9B—H92B | 0.9638 |
C8A—C9A | 1.544 (5) | C9B—H93B | 0.9638 |
C8A—H81A | 1.0584 | C10B—C11B | 1.517 (6) |
C9A—H91A | 1.0007 | C10B—H12B | 1.0300 |
C9A—H92A | 1.0007 | C10B—H13B | 1.0300 |
C9A—H93A | 1.0007 | C11B—H14B | 0.9834 |
C10A—C11A | 1.524 (6) | C11B—H15B | 0.9834 |
C10A—H12A | 1.0007 | C11B—H16B | 0.9834 |
C10A—H13A | 1.0007 | N1C—H1C | 0.857 (19) |
C11A—H14A | 0.9813 | N1C—H2C | 0.885 (19) |
C11A—H15A | 0.9813 | N1C—H3C | 0.869 (19) |
C11A—H16A | 0.9813 | N1C—H4C | 0.85 (2) |
O1B—C6B | 1.257 (4) | N1D—H1D | 0.86 (2) |
O2B—C12B | 1.267 (4) | N1D—H2D | 0.876 (19) |
O3B—C12B | 1.255 (4) | N1D—H3D | 0.888 (19) |
N1B—C1B | 1.477 (5) | N1D—H4D | 0.86 (2) |
| | | |
C1A—N1A—H1A | 114 (3) | N1B—C1B—C6B | 108.6 (3) |
C1A—N1A—H2A | 112 (3) | N1B—C1B—C2B | 110.3 (3) |
H1A—N1A—H2A | 108 (4) | C6B—C1B—C2B | 110.5 (3) |
C6A—N2A—C7A | 124.9 (3) | N1B—C1B—H11B | 109.1 |
C6A—N2A—H4A | 116 (3) | C6B—C1B—H11B | 109.1 |
C7A—N2A—H4A | 116 (3) | C2B—C1B—H11B | 109.1 |
N1A—C1A—C6A | 108.5 (3) | C3B—C2B—C1B | 111.6 (3) |
N1A—C1A—C2A | 109.5 (3) | C3B—C2B—C4B | 111.4 (3) |
C6A—C1A—C2A | 111.3 (3) | C1B—C2B—C4B | 111.5 (3) |
N1A—C1A—H11A | 109.2 | C3B—C2B—H21B | 107.4 |
C6A—C1A—H11A | 109.2 | C1B—C2B—H21B | 107.4 |
C2A—C1A—H11A | 109.2 | C4B—C2B—H21B | 107.4 |
C3A—C2A—C1A | 112.7 (3) | C2B—C3B—H31B | 109.5 |
C3A—C2A—C4A | 110.7 (4) | C2B—C3B—H32B | 109.5 |
C1A—C2A—C4A | 109.4 (4) | H31B—C3B—H32B | 109.5 |
C3A—C2A—H21A | 108.0 | C2B—C3B—H33B | 109.5 |
C1A—C2A—H21A | 108.0 | H31B—C3B—H33B | 109.5 |
C4A—C2A—H21A | 108.0 | H32B—C3B—H33B | 109.5 |
C2A—C3A—H31A | 109.5 | C5B—C4B—C2B | 114.4 (4) |
C2A—C3A—H32A | 109.5 | C5B—C4B—H41B | 108.7 |
H31A—C3A—H32A | 109.5 | C2B—C4B—H41B | 108.7 |
C2A—C3A—H33A | 109.5 | C5B—C4B—H42B | 108.7 |
H31A—C3A—H33A | 109.5 | C2B—C4B—H42B | 108.7 |
H32A—C3A—H33A | 109.5 | H41B—C4B—H42B | 107.6 |
C5A—C4A—C2A | 114.5 (5) | C4B—C5B—H51B | 109.5 |
C5A—C4A—H41A | 108.6 | C4B—C5B—H52B | 109.5 |
C2A—C4A—H41A | 108.6 | H51B—C5B—H52B | 109.5 |
C5A—C4A—H42A | 108.6 | C4B—C5B—H53B | 109.5 |
C2A—C4A—H42A | 108.6 | H51B—C5B—H53B | 109.5 |
H41A—C4A—H42A | 107.6 | H52B—C5B—H53B | 109.5 |
C4A—C5A—H51A | 109.5 | O1B—C6B—N2B | 123.0 (3) |
C4A—C5A—H52A | 109.5 | O1B—C6B—C1B | 121.5 (3) |
H51A—C5A—H52A | 109.5 | N2B—C6B—C1B | 115.5 (4) |
C4A—C5A—H53A | 109.5 | N2B—C7B—C12B | 108.0 (3) |
H51A—C5A—H53A | 109.5 | N2B—C7B—C8B | 111.2 (3) |
H52A—C5A—H53A | 109.5 | C12B—C7B—C8B | 112.4 (3) |
O1A—C6A—N2A | 122.7 (4) | N2B—C7B—H71B | 108.4 |
O1A—C6A—C1A | 121.3 (4) | C12B—C7B—H71B | 108.4 |
N2A—C6A—C1A | 116.0 (3) | C8B—C7B—H71B | 108.4 |
N2A—C7A—C12A | 108.1 (3) | C9B—C8B—C10B | 112.4 (3) |
N2A—C7A—C8A | 112.3 (3) | C9B—C8B—C7B | 112.4 (3) |
C12A—C7A—C8A | 112.5 (3) | C10B—C8B—C7B | 110.1 (3) |
N2A—C7A—H71A | 107.9 | C9B—C8B—H81B | 107.2 |
C12A—C7A—H71A | 107.9 | C10B—C8B—H81B | 107.2 |
C8A—C7A—H71A | 107.9 | C7B—C8B—H81B | 107.2 |
C10A—C8A—C9A | 111.8 (3) | C8B—C9B—H91B | 109.5 |
C10A—C8A—C7A | 111.7 (3) | C8B—C9B—H92B | 109.5 |
C9A—C8A—C7A | 111.4 (3) | H91B—C9B—H92B | 109.5 |
C10A—C8A—H81A | 107.2 | C8B—C9B—H93B | 109.5 |
C9A—C8A—H81A | 107.2 | H91B—C9B—H93B | 109.5 |
C7A—C8A—H81A | 107.2 | H92B—C9B—H93B | 109.5 |
C8A—C9A—H91A | 109.5 | C11B—C10B—C8B | 113.9 (3) |
C8A—C9A—H92A | 109.5 | C11B—C10B—H12B | 108.8 |
H91A—C9A—H92A | 109.5 | C8B—C10B—H12B | 108.8 |
C8A—C9A—H93A | 109.5 | C11B—C10B—H13B | 108.8 |
H91A—C9A—H93A | 109.5 | C8B—C10B—H13B | 108.8 |
H92A—C9A—H93A | 109.5 | H12B—C10B—H13B | 107.7 |
C11A—C10A—C8A | 114.4 (3) | C10B—C11B—H14B | 109.5 |
C11A—C10A—H12A | 108.7 | C10B—C11B—H15B | 109.5 |
C8A—C10A—H12A | 108.7 | H14B—C11B—H15B | 109.5 |
C11A—C10A—H13A | 108.7 | C10B—C11B—H16B | 109.5 |
C8A—C10A—H13A | 108.7 | H14B—C11B—H16B | 109.5 |
H12A—C10A—H13A | 107.6 | H15B—C11B—H16B | 109.5 |
C10A—C11A—H14A | 109.5 | O3B—C12B—O2B | 125.7 (3) |
C10A—C11A—H15A | 109.5 | O3B—C12B—C7B | 116.8 (3) |
H14A—C11A—H15A | 109.5 | O2B—C12B—C7B | 117.4 (3) |
C10A—C11A—H16A | 109.5 | H1C—N1C—H2C | 107 (4) |
H14A—C11A—H16A | 109.5 | H1C—N1C—H3C | 110 (4) |
H15A—C11A—H16A | 109.5 | H2C—N1C—H3C | 110 (4) |
O3A—C12A—O2A | 124.7 (3) | H1C—N1C—H4C | 99 (4) |
O3A—C12A—C7A | 117.7 (3) | H2C—N1C—H4C | 108 (4) |
O2A—C12A—C7A | 117.6 (3) | H3C—N1C—H4C | 121 (4) |
C1B—N1B—H1B | 106 (3) | H1D—N1D—H2D | 108 (4) |
C1B—N1B—H2B | 102 (3) | H1D—N1D—H3D | 114 (4) |
H1B—N1B—H2B | 106 (4) | H2D—N1D—H3D | 113 (4) |
C6B—N2B—C7B | 124.7 (3) | H1D—N1D—H4D | 119 (4) |
C6B—N2B—H4B | 111 (4) | H2D—N1D—H4D | 102 (4) |
C7B—N2B—H4B | 124 (4) | H3D—N1D—H4D | 100 (4) |
| | | |
N1A—C1A—C2A—C3A | 167.1 (4) | N1B—C1B—C2B—C3B | 178.9 (3) |
C6A—C1A—C2A—C3A | 47.1 (5) | C6B—C1B—C2B—C3B | 58.9 (4) |
N1A—C1A—C2A—C4A | −69.4 (4) | N1B—C1B—C2B—C4B | −55.8 (4) |
C6A—C1A—C2A—C4A | 170.6 (4) | C6B—C1B—C2B—C4B | −175.9 (4) |
C3A—C2A—C4A—C5A | −65.8 (6) | C3B—C2B—C4B—C5B | 69.1 (5) |
C1A—C2A—C4A—C5A | 169.5 (4) | C1B—C2B—C4B—C5B | −56.3 (5) |
C7A—N2A—C6A—O1A | −4.7 (6) | C7B—N2B—C6B—O1B | −3.0 (6) |
C7A—N2A—C6A—C1A | 175.3 (3) | C7B—N2B—C6B—C1B | 177.8 (3) |
N1A—C1A—C6A—O1A | 148.0 (3) | N1B—C1B—C6B—O1B | 145.5 (4) |
C2A—C1A—C6A—O1A | −91.5 (4) | C2B—C1B—C6B—O1B | −93.4 (4) |
N1A—C1A—C6A—N2A | −32.0 (4) | N1B—C1B—C6B—N2B | −35.2 (4) |
C2A—C1A—C6A—N2A | 88.5 (4) | C2B—C1B—C6B—N2B | 85.9 (4) |
C6A—N2A—C7A—C12A | −137.1 (4) | C6B—N2B—C7B—C12B | −138.9 (4) |
C6A—N2A—C7A—C8A | 98.2 (4) | C6B—N2B—C7B—C8B | 97.4 (4) |
N2A—C7A—C8A—C10A | −174.3 (3) | N2B—C7B—C8B—C9B | 58.1 (4) |
C12A—C7A—C8A—C10A | 63.5 (4) | C12B—C7B—C8B—C9B | −63.0 (4) |
N2A—C7A—C8A—C9A | 59.9 (4) | N2B—C7B—C8B—C10B | −175.7 (3) |
C12A—C7A—C8A—C9A | −62.3 (4) | C12B—C7B—C8B—C10B | 63.1 (4) |
C9A—C8A—C10A—C11A | −61.3 (5) | C9B—C8B—C10B—C11B | −64.9 (5) |
C7A—C8A—C10A—C11A | 173.1 (3) | C7B—C8B—C10B—C11B | 169.0 (3) |
N2A—C7A—C12A—O3A | 151.4 (3) | N2B—C7B—C12B—O3B | 151.3 (3) |
C8A—C7A—C12A—O3A | −84.0 (4) | C8B—C7B—C12B—O3B | −85.7 (4) |
N2A—C7A—C12A—O2A | −28.9 (5) | N2B—C7B—C12B—O2B | −29.2 (5) |
C8A—C7A—C12A—O2A | 95.7 (4) | C8B—C7B—C12B—O2B | 93.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1Bi | 0.93 (5) | 2.40 (5) | 3.323 (5) | 174 (4) |
N1A—H2A···O1Ai | 0.89 (5) | 2.56 (5) | 3.410 (5) | 162 (4) |
N2A—H4A···O2A | 0.85 (4) | 2.26 (4) | 2.666 (4) | 109 (3) |
N2A—H4A···N1A | 0.85 (4) | 2.27 (4) | 2.698 (5) | 112 (3) |
N1B—H1B···O1A | 0.93 (5) | 2.43 (5) | 3.318 (5) | 158 (4) |
N1B—H2B···O1Bi | 0.85 (5) | 2.68 (5) | 3.451 (4) | 153 (4) |
N2B—H4B···O2B | 0.73 (4) | 2.44 (5) | 2.681 (4) | 102 (4) |
N2B—H4B···N1B | 0.73 (4) | 2.28 (4) | 2.700 (5) | 118 (4) |
N1C—H1C···O1A | 0.86 (2) | 2.01 (2) | 2.862 (4) | 173 (4) |
N1C—H2C···O2B | 0.88 (2) | 1.89 (2) | 2.768 (4) | 174 (4) |
N1C—H3C···O3Aii | 0.87 (2) | 1.93 (2) | 2.777 (4) | 166 (4) |
N1C—H4C···O3Bi | 0.85 (2) | 2.03 (2) | 2.863 (4) | 165 (4) |
N1D—H1D···O1B | 0.86 (2) | 2.02 (2) | 2.882 (4) | 172 (4) |
N1D—H2D···O2Aiii | 0.88 (2) | 1.93 (2) | 2.779 (4) | 164 (4) |
N1D—H3D···O3Biv | 0.89 (2) | 1.90 (2) | 2.764 (4) | 164 (4) |
N1D—H4D···O3A | 0.86 (2) | 1.98 (2) | 2.829 (4) | 170 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x, y+1, z. |
Experimental details
| (IIc) | (IIdc) | (IIz) | (IIa) |
Crystal data |
Chemical formula | C13.08H25N3O6 | C13.80H27.20N3.40O4.70 | C12H28N2O5 | C12H27N3O3 |
Mr | 320.36 | 315.99 | 280.36 | 261.37 |
Crystal system, space group | Trigonal, P3121 | Orthorhombic, P21212 | Orthorhombic, P212121 | Triclinic, P1 |
Temperature (K) | 105 | 105 | 105 | 105 |
a, b, c (Å) | 16.0682 (6), 16.0682 (6), 11.5317 (9) | 16.2957 (19), 23.426 (2), 9.5842 (9) | 7.6341 (3), 12.5335 (6), 16.3923 (7) | 6.7765 (15), 9.718 (2), 11.882 (3) |
α, β, γ (°) | 90, 90, 120 | 90, 90, 90 | 90, 90, 90 | 81.580 (3), 80.484 (3), 88.350 (3) |
V (Å3) | 2578.4 (2) | 3658.7 (7) | 1568.45 (12) | 763.4 (3) |
Z | 6 | 8 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.09 | 0.09 | 0.08 |
Crystal size (mm) | 0.25 × 0.06 × 0.05 | 0.55 × 0.42 × 0.05 | 1.10 × 0.45 × 0.25 | 0.55 × 0.24 × 0.22 |
|
Data collection |
Diffractometer | Siemens SMART CCD diffractometer | Siemens SMART CCD diffractometer | Siemens SMART CCD diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) SADABS (Sheldrick, 1996) | Empirical (using intensity measurements) SADABS (Sheldrick, 1996) | Empirical (using intensity measurements) SADABS (Sheldrick, 1996) | Empirical (using intensity measurements) SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.968, 0.995 | 0.804, 0.996 | 0.848, 0.978 | 0.779, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11629, 3401, 2352 | 27666, 3657, 3276 | 21646, 6861, 6294 | 6449, 3063, 2165 |
Rint | 0.116 | 0.043 | 0.022 | 0.045 |
(sin θ/λ)max (Å−1) | 0.625 | 0.597 | 0.806 | 0.625 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.181, 1.06 | 0.047, 0.129, 1.14 | 0.029, 0.080, 1.05 | 0.044, 0.108, 0.98 |
No. of reflections | 3401 | 3657 | 6861 | 3063 |
No. of parameters | 245 | 449 | 210 | 395 |
No. of restraints | 0 | 48 | 0 | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.35 | 0.21, −0.31 | 0.32, −0.16 | 0.32, −0.23 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −1.8 (19) | −4.9 (15) | −0.2 (4) | −0.7 (14) |
Hydrogen-bond geometry (Å, º) for (IIc) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H5A···O1Bi | 0.79 (5) | 2.01 (5) | 2.745 (5) | 153 (5) |
O2A—H5A···O1Ci | 0.79 (5) | 1.80 (5) | 2.543 (5) | 156 (5) |
N1A—H1A···O3Aii | 0.91 | 2.17 | 3.051 (4) | 161 |
N1A—H2A···O1Biii | 0.91 | 2.29 | 2.914 (6) | 126 |
N1A—H2A···O1Ciii | 0.91 | 2.05 | 2.824 (6) | 142 |
N1A—H2A···O3Aiv | 0.91 | 2.53 | 3.258 (4) | 137 |
N1A—H3A···O2C | 0.91 | 2.52 | 3.187 (8) | 130 |
N1A—H3A···O3B | 0.91 | 2.26 | 3.146 (8) | 165 |
N1A—H3A···O3C | 0.91 | 1.82 | 2.726 (9) | 172 |
N2A—H4A···O3Bii | 0.88 | 2.14 | 2.981 (8) | 161 |
N2A—H4A···O3Cii | 0.88 | 2.18 | 3.028 (4) | 161 |
C1A—H11A···O1Aii | 1.00 | 2.42 | 2.999 (4) | 116 |
C1A—H11A···O3Bii | 1.00 | 2.45 | 3.262 (9) | 138 |
Symmetry codes: (i) −x+1, −x+y, −z+1/3; (ii) −y+1, x−y, z+1/3; (iii) y, x, −z+1; (iv) −x+y+1, −x+1, z+2/3. |
Hydrogen-bond geometry (Å, º) for (IIdc) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3B—H5B···O3A | 1.12 (3) | 1.31 (3) | 2.429 (3) | 173 (3) |
N1A—H1A···N1Ei | 0.89 | 2.23 | 2.952 (5) | 138 |
N1A—H1A···O2Cii | 0.89 | 2.24 | 2.745 (7) | 115 |
N1A—H2A···O2Ai | 0.89 | 2.00 | 2.841 (3) | 156 |
N1A—H2A···O3Ai | 0.89 | 2.47 | 3.188 (3) | 139 |
N1A—H3A···O2Bii | 0.89 | 2.02 | 2.843 (3) | 154 |
N2A—H4A···O1Bi | 0.86 | 2.21 | 3.033 (3) | 161 |
C1A—H11A···O1Bi | 0.98 | 2.36 | 3.244 (3) | 150 |
N1B—H1B···O3Ciii | 0.89 | 1.90 | 2.782 (15) | 173 |
N1B—H1B···O1Diii | 0.89 | 2.20 | 2.88 (3) | 133 |
N1B—H2B···O2Biii | 0.89 | 2.02 | 2.865 (3) | 158 |
N1B—H2B···O3Biii | 0.89 | 2.50 | 3.223 (3) | 139 |
N1B—H3B···O2Aiv | 0.89 | 2.00 | 2.828 (3) | 155 |
N2B—H4B···O1Aiii | 0.86 | 2.16 | 2.989 (3) | 162 |
C1B—H11B···O1Aiii | 0.98 | 2.33 | 3.215 (3) | 150 |
C2F—H3F···O1C | 0.96 | 1.91 | 2.827 (3) | 158 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z+1; (iii) x−1/2, −y+3/2, −z+1; (iv) x−1/2, −y+3/2, −z. |
Hydrogen-bond geometry (Å, º) for (IIz) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.928 (11) | 1.814 (11) | 2.7293 (7) | 168.7 (10) |
N1—H2···O2w | 0.835 (11) | 2.001 (12) | 2.7920 (7) | 157.8 (11) |
N1—H3···O2Wii | 0.903 (10) | 1.959 (10) | 2.8502 (7) | 169.2 (10) |
N2—H4···O1Wiii | 0.831 (11) | 2.173 (11) | 2.9905 (8) | 167.9 (9) |
O1W—H11W···O3i | 0.811 (16) | 1.997 (16) | 2.7968 (7) | 168.5 (15) |
O1W—H12W···O2iv | 0.801 (17) | 2.364 (15) | 2.9487 (8) | 130.6 (14) |
O2W—H21W···O1v | 0.772 (12) | 1.969 (13) | 2.7271 (7) | 167.5 (12) |
O2W—H22W···O3i | 0.870 (12) | 1.792 (13) | 2.6582 (7) | 173.6 (11) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, −z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x+1, y, z. |
Hydrogen-bond geometry (Å, º) for (IIa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1Bi | 0.93 (5) | 2.40 (5) | 3.323 (5) | 174 (4) |
N1A—H2A···O1Ai | 0.89 (5) | 2.56 (5) | 3.410 (5) | 162 (4) |
N2A—H4A···O2A | 0.85 (4) | 2.26 (4) | 2.666 (4) | 109 (3) |
N2A—H4A···N1A | 0.85 (4) | 2.27 (4) | 2.698 (5) | 112 (3) |
N1B—H1B···O1A | 0.93 (5) | 2.43 (5) | 3.318 (5) | 158 (4) |
N1B—H2B···O1Bi | 0.85 (5) | 2.68 (5) | 3.451 (4) | 153 (4) |
N2B—H4B···O2B | 0.73 (4) | 2.44 (5) | 2.681 (4) | 102 (4) |
N2B—H4B···N1B | 0.73 (4) | 2.28 (4) | 2.700 (5) | 118 (4) |
N1C—H1C···O1A | 0.86 (2) | 2.01 (2) | 2.862 (4) | 173 (4) |
N1C—H2C···O2B | 0.88 (2) | 1.89 (2) | 2.768 (4) | 174 (4) |
N1C—H3C···O3Aii | 0.87 (2) | 1.93 (2) | 2.777 (4) | 166 (4) |
N1C—H4C···O3Bi | 0.85 (2) | 2.03 (2) | 2.863 (4) | 165 (4) |
N1D—H1D···O1B | 0.86 (2) | 2.02 (2) | 2.882 (4) | 172 (4) |
N1D—H2D···O2Aiii | 0.88 (2) | 1.93 (2) | 2.779 (4) | 164 (4) |
N1D—H3D···O3Biv | 0.89 (2) | 1.90 (2) | 2.764 (4) | 164 (4) |
N1D—H4D···O3A | 0.86 (2) | 1.98 (2) | 2.829 (4) | 170 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x, y+1, z. |
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