Supporting information
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618007151/aw5008sup3.pdf | |
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618007151/aw5008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618007151/aw5008Isup2.hkl |
CCDC reference: 1825080
Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: APEX2 (Bruker, 2014); program(s) used to solve structure: APEX2 (Bruker, 2014); program(s) used to refine structure: SHELXT (Sheldrick, 2015a); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).
C11H22N2O3·C2H3N | Dx = 1.165 Mg m−3 |
Mr = 271.36 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 858 reflections |
a = 5.341 (3) Å | θ = 2.5–20.7° |
b = 13.536 (6) Å | µ = 0.08 mm−1 |
c = 21.406 (8) Å | T = 100 K |
V = 1547.6 (12) Å3 | Plate, colorless |
Z = 4 | 0.42 × 0.15 × 0.01 mm |
F(000) = 592 |
Bruker D8 Venture with Photon 100 CMOS detector diffractometer | 1572 independent reflections |
Radiation source: fine-focus sealed tube | 903 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.190 |
Detector resolution: 8.3 pixels mm-1 | θmax = 20.8°, θmin = 2.4° |
Sets of exposures each taken over 0.5° ω rotation scans | h = −5→4 |
Absorption correction: multi-scan SADABS (Bruker, 2014) | k = −13→12 |
Tmin = 0.612, Tmax = 1.000 | l = −21→19 |
6287 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.082 | w = 1/[σ2(Fo2) + (0.0807P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.184 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.26 e Å−3 |
1572 reflections | Δρmin = −0.28 e Å−3 |
140 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
72 restraints | Extinction coefficient: 0.093 (13) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Non-terminal C-atoms refined isotropically due to poor reflection-to-parameter ratio. All H atoms in theoretical positions. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0880 (14) | 0.6221 (6) | 0.2086 (3) | 0.029 (2) | |
O2 | 0.0294 (16) | 0.3336 (5) | 0.2523 (3) | 0.028 (2) | |
O3 | −0.3193 (14) | 0.3338 (5) | 0.1909 (3) | 0.023 (2) | |
N1 | 0.5574 (18) | 0.7039 (6) | 0.2281 (4) | 0.025 (3) | |
H1 | 0.5398 | 0.7151 | 0.1864 | 0.037* | |
H2 | 0.7148 | 0.7210 | 0.2402 | 0.037* | |
H3 | 0.4436 | 0.7408 | 0.2495 | 0.037* | |
N2 | 0.2677 (18) | 0.4746 (6) | 0.1816 (3) | 0.018 (3) | |
H4 | 0.4091 | 0.4414 | 0.1792 | 0.022* | |
C1 | 0.513 (2) | 0.5941 (7) | 0.2418 (5) | 0.022 (3)* | |
H11 | 0.6553 | 0.5547 | 0.2242 | 0.026* | |
C2 | 0.503 (2) | 0.5788 (7) | 0.3127 (5) | 0.024 (3)* | |
H2A | 0.3637 | 0.6196 | 0.3303 | 0.029* | |
C3 | 0.455 (2) | 0.4695 (8) | 0.3284 (5) | 0.031 (4) | |
H31 | 0.4490 | 0.4611 | 0.3738 | 0.046* | |
H32 | 0.2953 | 0.4487 | 0.3101 | 0.046* | |
H33 | 0.5907 | 0.4290 | 0.3111 | 0.046* | |
C4 | 0.756 (2) | 0.6102 (8) | 0.3446 (5) | 0.034 (4) | |
H41 | 0.7440 | 0.5997 | 0.3898 | 0.051* | |
H42 | 0.8932 | 0.5703 | 0.3277 | 0.051* | |
H43 | 0.7884 | 0.6802 | 0.3362 | 0.051* | |
C5 | 0.270 (3) | 0.5645 (9) | 0.2086 (5) | 0.026 (3)* | |
C6 | 0.037 (2) | 0.4292 (7) | 0.1560 (5) | 0.024 (3)* | |
H61 | −0.0846 | 0.4834 | 0.1469 | 0.028* | |
C7 | 0.094 (2) | 0.3760 (8) | 0.0945 (4) | 0.020 (3)* | |
H71 | −0.0575 | 0.3399 | 0.0811 | 0.025* | |
H72 | 0.2274 | 0.3266 | 0.1022 | 0.025* | |
C8 | 0.180 (2) | 0.4454 (8) | 0.0401 (5) | 0.022 (3)* | |
H81 | 0.3251 | 0.4851 | 0.0555 | 0.026* | |
C9 | −0.030 (2) | 0.5183 (8) | 0.0217 (5) | 0.037 (4) | |
H91 | −0.0821 | 0.5560 | 0.0586 | 0.056* | |
H92 | 0.0322 | 0.5637 | −0.0104 | 0.056* | |
H93 | −0.1734 | 0.4813 | 0.0052 | 0.056* | |
C10 | 0.269 (2) | 0.3846 (8) | −0.0147 (4) | 0.032 (4) | |
H101 | 0.4019 | 0.3396 | −0.0009 | 0.048* | |
H102 | 0.1292 | 0.3463 | −0.0315 | 0.048* | |
H103 | 0.3348 | 0.4286 | −0.0472 | 0.048* | |
C11 | −0.087 (3) | 0.3579 (8) | 0.2046 (5) | 0.024 (3)* | |
C13 | 0.032 (2) | 0.8103 (9) | 0.0897 (5) | 0.047 (4) | |
H131 | 0.0379 | 0.8689 | 0.0629 | 0.070* | |
H132 | 0.0140 | 0.8308 | 0.1334 | 0.070* | |
H133 | −0.1104 | 0.7689 | 0.0778 | 0.070* | |
C12 | 0.265 (3) | 0.7538 (10) | 0.0825 (6) | 0.038 (4) | |
N3 | 0.450 (2) | 0.7083 (8) | 0.0788 (5) | 0.043 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.012 (5) | 0.038 (5) | 0.038 (5) | 0.001 (4) | 0.000 (4) | −0.007 (4) |
O2 | 0.021 (6) | 0.040 (5) | 0.022 (4) | 0.003 (5) | −0.004 (4) | 0.008 (4) |
O3 | 0.007 (5) | 0.029 (5) | 0.033 (5) | 0.001 (4) | 0.003 (4) | −0.001 (4) |
N1 | 0.015 (7) | 0.040 (6) | 0.019 (5) | −0.005 (6) | 0.003 (5) | 0.000 (5) |
N2 | 0.010 (5) | 0.026 (4) | 0.019 (4) | 0.005 (4) | −0.002 (4) | −0.002 (4) |
C3 | 0.026 (9) | 0.048 (8) | 0.019 (7) | 0.006 (8) | −0.003 (7) | 0.000 (6) |
C4 | 0.027 (9) | 0.049 (8) | 0.025 (7) | 0.008 (9) | −0.010 (7) | −0.003 (6) |
C9 | 0.041 (10) | 0.041 (7) | 0.030 (7) | −0.010 (8) | −0.001 (7) | 0.001 (6) |
C10 | 0.027 (9) | 0.047 (8) | 0.022 (7) | 0.004 (8) | 0.004 (7) | −0.001 (6) |
C13 | 0.015 (9) | 0.064 (9) | 0.062 (9) | 0.008 (8) | −0.001 (8) | −0.004 (7) |
C12 | 0.031 (8) | 0.051 (8) | 0.032 (7) | −0.004 (7) | 0.001 (7) | −0.003 (6) |
N3 | 0.037 (9) | 0.048 (7) | 0.045 (7) | −0.005 (7) | −0.003 (7) | 0.002 (6) |
O1—C5 | 1.246 (13) | C4—H43 | 0.9800 |
O2—C11 | 1.238 (12) | C6—C7 | 1.530 (13) |
O3—C11 | 1.317 (13) | C6—C11 | 1.566 (14) |
N1—C1 | 1.534 (12) | C6—H61 | 1.0000 |
N1—H1 | 0.9100 | C7—C8 | 1.565 (13) |
N1—H2 | 0.9100 | C7—H71 | 0.9900 |
N1—H3 | 0.9100 | C7—H72 | 0.9900 |
N2—C5 | 1.347 (12) | C8—C10 | 1.509 (13) |
N2—C6 | 1.482 (14) | C8—C9 | 1.544 (14) |
N2—H4 | 0.8800 | C8—H81 | 1.0000 |
C1—C2 | 1.533 (14) | C9—H91 | 0.9800 |
C1—C5 | 1.535 (17) | C9—H92 | 0.9800 |
C1—H11 | 1.0000 | C9—H93 | 0.9800 |
C2—C3 | 1.538 (13) | C10—H101 | 0.9800 |
C2—C4 | 1.573 (16) | C10—H102 | 0.9800 |
C2—H2A | 1.0000 | C10—H103 | 0.9800 |
C3—H31 | 0.9800 | C13—C12 | 1.468 (18) |
C3—H32 | 0.9800 | C13—H131 | 0.9800 |
C3—H33 | 0.9800 | C13—H132 | 0.9800 |
C4—H41 | 0.9800 | C13—H133 | 0.9800 |
C4—H42 | 0.9800 | C12—N3 | 1.165 (15) |
C1—N1—H1 | 109.5 | C7—C6—C11 | 111.5 (8) |
C1—N1—H2 | 109.5 | N2—C6—H61 | 107.9 |
H1—N1—H2 | 109.5 | C7—C6—H61 | 107.9 |
C1—N1—H3 | 109.5 | C11—C6—H61 | 107.9 |
H1—N1—H3 | 109.5 | C6—C7—C8 | 114.7 (8) |
H2—N1—H3 | 109.5 | C6—C7—H71 | 108.6 |
C5—N2—C6 | 122.8 (11) | C8—C7—H71 | 108.6 |
C5—N2—H4 | 118.6 | C6—C7—H72 | 108.6 |
C6—N2—H4 | 118.6 | C8—C7—H72 | 108.6 |
C2—C1—N1 | 109.0 (8) | H71—C7—H72 | 107.6 |
C2—C1—C5 | 113.1 (10) | C10—C8—C9 | 112.3 (9) |
N1—C1—C5 | 107.1 (9) | C10—C8—C7 | 110.1 (9) |
C2—C1—H11 | 109.2 | C9—C8—C7 | 111.2 (10) |
N1—C1—H11 | 109.2 | C10—C8—H81 | 107.7 |
C5—C1—H11 | 109.2 | C9—C8—H81 | 107.7 |
C1—C2—C3 | 110.6 (8) | C7—C8—H81 | 107.7 |
C1—C2—C4 | 111.2 (10) | C8—C9—H91 | 109.5 |
C3—C2—C4 | 107.9 (10) | C8—C9—H92 | 109.5 |
C1—C2—H2A | 109.0 | H91—C9—H92 | 109.5 |
C3—C2—H2A | 109.0 | C8—C9—H93 | 109.5 |
C4—C2—H2A | 109.0 | H91—C9—H93 | 109.5 |
C2—C3—H31 | 109.5 | H92—C9—H93 | 109.5 |
C2—C3—H32 | 109.5 | C8—C10—H101 | 109.5 |
H31—C3—H32 | 109.5 | C8—C10—H102 | 109.5 |
C2—C3—H33 | 109.5 | H101—C10—H102 | 109.5 |
H31—C3—H33 | 109.5 | C8—C10—H103 | 109.5 |
H32—C3—H33 | 109.5 | H101—C10—H103 | 109.5 |
C2—C4—H41 | 109.5 | H102—C10—H103 | 109.5 |
C2—C4—H42 | 109.5 | O2—C11—O3 | 126.2 (11) |
H41—C4—H42 | 109.5 | O2—C11—C6 | 120.0 (12) |
C2—C4—H43 | 109.5 | O3—C11—C6 | 113.7 (11) |
H41—C4—H43 | 109.5 | C12—C13—H131 | 109.5 |
H42—C4—H43 | 109.5 | C12—C13—H132 | 109.5 |
O1—C5—N2 | 123.9 (12) | H131—C13—H132 | 109.5 |
O1—C5—C1 | 119.8 (11) | C12—C13—H133 | 109.5 |
N2—C5—C1 | 116.2 (12) | H131—C13—H133 | 109.5 |
N2—C6—C7 | 110.3 (10) | H132—C13—H133 | 109.5 |
N2—C6—C11 | 111.1 (9) | N3—C12—C13 | 177.7 (15) |
N1—C1—C2—C3 | 179.2 (9) | C5—N2—C6—C7 | 139.9 (9) |
C5—C1—C2—C3 | 60.2 (14) | C5—N2—C6—C11 | −95.9 (11) |
N1—C1—C2—C4 | −60.9 (13) | N2—C6—C7—C8 | −65.0 (12) |
C5—C1—C2—C4 | −179.9 (9) | C11—C6—C7—C8 | 171.0 (10) |
C6—N2—C5—O1 | −8.0 (17) | C6—C7—C8—C10 | 171.2 (10) |
C6—N2—C5—C1 | 170.7 (9) | C6—C7—C8—C9 | −63.6 (13) |
C2—C1—C5—O1 | 79.9 (13) | N2—C6—C11—O2 | −11.7 (14) |
N1—C1—C5—O1 | −40.2 (14) | C7—C6—C11—O2 | 111.9 (12) |
C2—C1—C5—N2 | −98.9 (12) | N2—C6—C11—O3 | 164.8 (9) |
N1—C1—C5—N2 | 140.9 (9) | C7—C6—C11—O3 | −71.7 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3 | 0.91 | 2.35 | 3.247 (12) | 167 |
N1—H2···O2i | 0.91 | 2.05 | 2.851 (13) | 146 |
N1—H2···O1ii | 0.91 | 2.50 | 3.071 (12) | 122 |
N1—H3···O3iii | 0.91 | 1.91 | 2.778 (11) | 158 |
N2—H4···O3ii | 0.88 | 2.07 | 2.922 (11) | 162 |
C1—H11···O1ii | 1.00 | 2.51 | 3.173 (15) | 124 |
C3—H32···O2 | 0.98 | 2.45 | 3.348 (14) | 153 |
C13—H132···O2iii | 0.98 | 2.46 | 3.413 (14) | 164 |
C13—H133···N3iv | 0.98 | 2.49 | 3.412 (17) | 157 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x−1, y, z. |