Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104014569/de5006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014569/de5006sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014569/de5006sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014569/de5006sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014569/de5006sup5.hkl |
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).
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 |
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 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) |
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 |
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 |
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 |
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. |
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) |
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) |
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. |
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. |
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 |
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 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) |
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 |
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 |
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 |
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. |
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) |
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) |
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. |
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. |
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 |
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 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) |
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 |
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 |
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 |
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. |
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* |
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) |
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) |
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. |
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 |
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 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) |
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)° |
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 |
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 |
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. |
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* |
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) |
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) |
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) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2001), SHELXTL (Bruker, 2000).
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. |
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. |
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. |
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. |