Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617011775/eb5064sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520617011775/eb5064Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617011775/eb5064sup3.pdf |
CCDC reference: 1568826
Data collection: CrystalClear (Rigaku/MSC Inc., 2000); cell refinement: CrystalClear (Rigaku/MSC Inc., 2000); data reduction: CrystalStructure 3.6.0 (Rigaku/MSC Inc., 2004); program(s) used to solve structure: SHELXS2016/6 (Sheldrick, 2016); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL2016/6 (Sheldrick, 2016).
C14H26N2O9 | F(000) = 784 |
Mr = 366.37 | Dx = 1.393 Mg m−3 Dm = 1.393 Mg m−3 Dm measured by not measured |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
a = 17.283 (3) Å | Cell parameters from 19530 reflections |
b = 5.7371 (8) Å | θ = 1.4–28.1° |
c = 18.561 (3) Å | µ = 0.12 mm−1 |
β = 108.274 (4)° | T = 291 K |
V = 1747.5 (5) Å3 | Rectangular, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
RIGAKU AFC7S Mercury diffractometer | 3558 independent reflections |
Radiation source: normal-focus sealed tube | 2320 reflections with I > 2σ(I) |
Detector resolution: 14.6306 pixels mm-1 | Rint = 0.062 |
ω scans | θmax = 28.1°, θmin = 1.4° |
Absorption correction: multi-scan Jacobson, R. (1998) | h = −20→20 |
Tmin = 0.937, Tmax = 0.948 | k = −7→5 |
19530 measured reflections | l = −22→22 |
Refinement on F2 | 88 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0662P)2 + 0.7567P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3558 reflections | Δρmax = 0.29 e Å−3 |
312 parameters | Δρmin = −0.29 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.71589 (14) | 0.4390 (4) | 0.35067 (15) | 0.0375 (5) | |
H11 | 0.706 (2) | 0.367 (6) | 0.302 (2) | 0.071 (10)* | |
H12 | 0.6919 (19) | 0.590 (6) | 0.3442 (17) | 0.062 (9)* | |
H13 | 0.6902 (18) | 0.374 (5) | 0.3777 (17) | 0.048 (9)* | |
O2 | 0.79780 (12) | 0.7041 (3) | 0.28638 (11) | 0.0531 (5) | |
O1 | 0.91798 (13) | 0.6401 (4) | 0.37413 (13) | 0.0684 (7) | |
H1 | 0.950 (3) | 0.763 (8) | 0.346 (3) | 0.127 (15)* | |
C1 | 0.84098 (17) | 0.6130 (5) | 0.34402 (16) | 0.0413 (7) | |
C2 | 0.80528 (15) | 0.4531 (4) | 0.39079 (14) | 0.0349 (6) | |
C3 | 0.84390 (18) | 0.2095 (5) | 0.40022 (17) | 0.0509 (8) | |
H3A | 0.803089 | 0.090831 | 0.397460 | 0.061* | |
H3B | 0.868400 | 0.179987 | 0.360702 | 0.061* | |
C4 | 0.9083 (5) | 0.2074 (15) | 0.4776 (4) | 0.061 (2) | 0.678 (18) |
H4A | 0.958 (2) | 0.289 (4) | 0.4774 (4) | 0.074* | 0.678 (18) |
H4B | 0.9219 (8) | 0.049 (7) | 0.4970 (9) | 0.074* | 0.678 (18) |
C5 | 0.8611 (6) | 0.3424 (19) | 0.5223 (6) | 0.073 (3) | 0.678 (18) |
H5A | 0.820 (2) | 0.242 (5) | 0.5328 (7) | 0.088* | 0.678 (18) |
H5B | 0.8982 (16) | 0.399 (3) | 0.571 (2) | 0.088* | 0.678 (18) |
C4B | 0.8718 (18) | 0.180 (3) | 0.4868 (7) | 0.079 (6) | 0.322 (18) |
H4B1 | 0.830 (5) | 0.100 (9) | 0.5015 (16) | 0.095* | 0.322 (18) |
H4B2 | 0.920 (5) | 0.086 (10) | 0.5022 (17) | 0.095* | 0.322 (18) |
C5B | 0.8889 (14) | 0.413 (3) | 0.5265 (13) | 0.074 (6) | 0.322 (18) |
H5B1 | 0.8834 (13) | 0.407 (3) | 0.584 (5) | 0.089* | 0.322 (18) |
H5B2 | 0.949 (5) | 0.482 (7) | 0.5290 (13) | 0.089* | 0.322 (18) |
C6 | 0.82099 (19) | 0.5444 (5) | 0.47241 (15) | 0.0491 (7) | |
H6A | 0.856654 | 0.679165 | 0.481995 | 0.059* | |
H6B | 0.770278 | 0.586859 | 0.481004 | 0.059* | |
N2 | 1.01369 (17) | 1.0784 (5) | 0.14719 (14) | 0.0463 (6) | |
H21 | 0.966 (2) | 1.192 (6) | 0.1395 (19) | 0.074 (10)* | |
H22 | 0.996 (3) | 0.939 (8) | 0.127 (2) | 0.109 (15)* | |
H23 | 1.047 (2) | 1.130 (5) | 0.1202 (18) | 0.062 (9)* | |
O3 | 0.94629 (12) | 0.7709 (3) | 0.20984 (12) | 0.0509 (5) | |
O4 | 0.99939 (14) | 0.9130 (4) | 0.32631 (12) | 0.0673 (7) | |
C7 | 0.99324 (16) | 0.8976 (4) | 0.25728 (16) | 0.0398 (6) | |
C8 | 1.05297 (15) | 1.0480 (4) | 0.23084 (14) | 0.0373 (6) | |
C9 | 1.07420 (18) | 1.2831 (5) | 0.27099 (17) | 0.0482 (7) | |
H9A | 1.065199 | 1.407492 | 0.233892 | 0.058* | |
H9B | 1.039890 | 1.311083 | 0.302640 | 0.058* | |
C10 | 1.1632 (7) | 1.278 (3) | 0.3195 (11) | 0.080 (5) | 0.52 (2) |
H10A | 1.1678 (8) | 1.311 (4) | 0.361 (3) | 0.096* | 0.52 (2) |
H10B | 1.189 (2) | 1.365 (7) | 0.3039 (17) | 0.096* | 0.52 (2) |
C11 | 1.1916 (8) | 1.028 (3) | 0.3147 (9) | 0.077 (4) | 0.48 (2) |
H11A | 1.242 (4) | 1.028 (3) | 0.3110 (9) | 0.092* | 0.48 (2) |
H11B | 1.1922 (8) | 0.949 (6) | 0.356 (3) | 0.092* | 0.48 (2) |
C10B | 1.1578 (9) | 1.240 (4) | 0.3264 (12) | 0.087 (6) | 0.48 (2) |
H10C | 1.1543 (9) | 1.135 (8) | 0.378 (3) | 0.104* | 0.48 (2) |
H10D | 1.192 (2) | 1.413 (11) | 0.3469 (17) | 0.104* | 0.48 (2) |
C11B | 1.1989 (4) | 1.1000 (17) | 0.2783 (9) | 0.058 (3) | 0.52 (2) |
H11C | 1.2084 (7) | 1.195 (5) | 0.238 (2) | 0.070* | 0.52 (2) |
H11D | 1.250 (3) | 1.031 (4) | 0.3093 (17) | 0.070* | 0.52 (2) |
C12 | 1.13470 (17) | 0.9188 (5) | 0.24734 (19) | 0.0524 (8) | |
H12A | 1.127897 | 0.754947 | 0.256729 | 0.063* | |
H12B | 1.155128 | 0.931891 | 0.204429 | 0.063* | |
C13 | 0.60324 (16) | −0.0480 (4) | 0.54309 (15) | 0.0382 (6) | |
C14 | 0.62234 (16) | 0.1935 (4) | 0.51573 (16) | 0.0399 (6) | |
O5 | 0.63155 (14) | −0.2189 (3) | 0.51124 (12) | 0.0544 (6) | |
H55 | 0.621 (2) | −0.349 (6) | 0.5271 (19) | 0.067 (10)* | |
O6 | 0.56691 (13) | −0.0716 (3) | 0.58792 (11) | 0.0520 (5) | |
O7 | 0.60949 (14) | 0.3630 (3) | 0.55320 (12) | 0.0596 (6) | |
O8 | 0.64709 (14) | 0.2030 (3) | 0.46069 (12) | 0.0559 (6) | |
O1W | 0.37498 (14) | 0.1441 (4) | 0.65001 (14) | 0.0499 (5) | |
H2W | 0.397 (3) | 0.035 (8) | 0.682 (2) | 0.106 (16)* | |
H1W | 0.363 (2) | 0.064 (7) | 0.607 (2) | 0.095 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0368 (14) | 0.0379 (14) | 0.0417 (14) | −0.0034 (10) | 0.0177 (11) | −0.0011 (11) |
O2 | 0.0491 (13) | 0.0630 (13) | 0.0456 (12) | −0.0036 (10) | 0.0125 (10) | 0.0179 (10) |
O1 | 0.0377 (13) | 0.0950 (17) | 0.0679 (15) | −0.0131 (11) | 0.0101 (11) | 0.0324 (13) |
C1 | 0.0392 (17) | 0.0408 (15) | 0.0451 (17) | −0.0018 (12) | 0.0148 (14) | 0.0043 (12) |
C2 | 0.0348 (15) | 0.0337 (13) | 0.0365 (14) | −0.0015 (10) | 0.0115 (11) | 0.0022 (10) |
C3 | 0.0511 (18) | 0.0391 (16) | 0.063 (2) | 0.0043 (13) | 0.0193 (16) | 0.0035 (13) |
C4 | 0.043 (4) | 0.052 (3) | 0.080 (4) | 0.006 (3) | 0.006 (3) | 0.014 (3) |
C5 | 0.074 (6) | 0.092 (6) | 0.038 (4) | 0.005 (4) | −0.007 (4) | 0.005 (4) |
C4B | 0.093 (14) | 0.060 (8) | 0.060 (9) | 0.026 (9) | −0.009 (9) | 0.008 (6) |
C5B | 0.056 (10) | 0.083 (10) | 0.059 (8) | 0.020 (8) | −0.019 (8) | −0.023 (8) |
C6 | 0.0579 (19) | 0.0511 (17) | 0.0379 (16) | −0.0066 (14) | 0.0146 (14) | −0.0036 (13) |
N2 | 0.0533 (17) | 0.0464 (15) | 0.0446 (15) | −0.0053 (13) | 0.0231 (13) | 0.0013 (11) |
O3 | 0.0444 (12) | 0.0472 (11) | 0.0598 (13) | −0.0130 (9) | 0.0145 (10) | −0.0049 (9) |
O4 | 0.0663 (15) | 0.0935 (17) | 0.0427 (13) | −0.0334 (12) | 0.0178 (11) | 0.0037 (11) |
C7 | 0.0345 (15) | 0.0387 (15) | 0.0459 (17) | 0.0005 (12) | 0.0120 (13) | 0.0070 (12) |
C8 | 0.0368 (15) | 0.0358 (14) | 0.0413 (15) | −0.0019 (11) | 0.0153 (12) | 0.0007 (11) |
C9 | 0.0548 (19) | 0.0361 (15) | 0.0562 (19) | −0.0041 (13) | 0.0210 (15) | −0.0032 (13) |
C10 | 0.050 (7) | 0.069 (9) | 0.100 (10) | −0.003 (5) | −0.006 (6) | −0.018 (6) |
C11 | 0.058 (5) | 0.084 (7) | 0.077 (7) | 0.012 (5) | 0.004 (5) | 0.004 (6) |
C10B | 0.105 (12) | 0.050 (7) | 0.087 (9) | −0.016 (6) | 0.002 (8) | −0.039 (7) |
C11B | 0.031 (4) | 0.055 (5) | 0.082 (7) | −0.007 (3) | 0.007 (4) | 0.002 (4) |
C12 | 0.0382 (17) | 0.0465 (17) | 0.074 (2) | 0.0005 (12) | 0.0196 (16) | −0.0058 (14) |
C13 | 0.0419 (16) | 0.0360 (14) | 0.0382 (15) | 0.0020 (12) | 0.0150 (13) | 0.0005 (11) |
C14 | 0.0439 (16) | 0.0362 (15) | 0.0425 (16) | −0.0001 (12) | 0.0175 (13) | 0.0030 (12) |
O5 | 0.0816 (16) | 0.0323 (11) | 0.0664 (14) | 0.0038 (10) | 0.0478 (12) | 0.0041 (10) |
O6 | 0.0708 (15) | 0.0443 (11) | 0.0561 (13) | 0.0021 (9) | 0.0419 (12) | 0.0061 (9) |
O7 | 0.0944 (17) | 0.0328 (11) | 0.0712 (15) | −0.0004 (10) | 0.0540 (13) | −0.0021 (9) |
O8 | 0.0865 (16) | 0.0414 (11) | 0.0553 (13) | −0.0116 (10) | 0.0448 (12) | −0.0020 (9) |
O1W | 0.0617 (14) | 0.0387 (11) | 0.0494 (13) | 0.0060 (10) | 0.0175 (11) | −0.0020 (10) |
N1—C2 | 1.492 (3) | O3—C7 | 1.230 (3) |
N1—H11 | 0.96 (4) | O4—C7 | 1.255 (3) |
N1—H12 | 0.95 (3) | O4—H1 | 1.35 (5) |
N1—H13 | 0.85 (3) | C7—C8 | 1.539 (4) |
O2—C1 | 1.214 (3) | C8—C9 | 1.529 (4) |
O1—C1 | 1.281 (3) | C8—C12 | 1.538 (4) |
O1—H1 | 1.11 (5) | C9—C10B | 1.507 (13) |
C1—C2 | 1.521 (4) | C9—C10 | 1.520 (10) |
C2—C3 | 1.535 (4) | C9—H9A | 0.9700 |
C2—C6 | 1.544 (4) | C9—H9B | 0.9700 |
C3—C4 | 1.517 (7) | C10—C11 | 1.526 (15) |
C3—C4B | 1.536 (13) | C10—H10A | 0.78 (6) |
C3—H3A | 0.9700 | C10—H10B | 0.78 (6) |
C3—H3B | 0.9700 | C11—C12 | 1.466 (9) |
C4—C5 | 1.542 (11) | C11—H11A | 0.89 (6) |
C4—H4A | 0.98 (4) | C11—H11B | 0.89 (6) |
C4—H4B | 0.98 (4) | C10B—C11B | 1.533 (15) |
C5—C6 | 1.509 (8) | C10B—H10C | 1.15 (7) |
C5—H5A | 0.98 (4) | C10B—H10D | 1.15 (7) |
C5—H5B | 0.98 (4) | C11B—C12 | 1.498 (7) |
C4B—C5B | 1.512 (16) | C11B—H11C | 0.98 (5) |
C4B—H4B1 | 0.96 (9) | C11B—H11D | 0.98 (5) |
C4B—H4B2 | 0.96 (9) | C12—H12A | 0.9700 |
C5B—C6 | 1.489 (13) | C12—H12B | 0.9700 |
C5B—H5B1 | 1.09 (9) | C13—O6 | 1.197 (3) |
C5B—H5B2 | 1.09 (9) | C13—O5 | 1.316 (3) |
C6—H6A | 0.9700 | C13—C14 | 1.546 (4) |
C6—H6B | 0.9700 | C14—O8 | 1.226 (3) |
N2—C8 | 1.497 (4) | C14—O7 | 1.255 (3) |
N2—H21 | 1.03 (4) | O5—H55 | 0.84 (4) |
N2—H22 | 0.90 (5) | O1W—H2W | 0.86 (5) |
N2—H23 | 0.92 (3) | O1W—H1W | 0.89 (4) |
C2—N1—H11 | 110 (2) | H21—N2—H23 | 109 (3) |
C2—N1—H12 | 110.8 (19) | H22—N2—H23 | 104 (3) |
H11—N1—H12 | 109 (3) | C7—O4—H1 | 112 (2) |
C2—N1—H13 | 112 (2) | O3—C7—O4 | 126.7 (3) |
H11—N1—H13 | 113 (3) | O3—C7—C8 | 117.4 (2) |
H12—N1—H13 | 101 (3) | O4—C7—C8 | 115.8 (2) |
C1—O1—H1 | 118 (2) | N2—C8—C9 | 111.4 (2) |
O2—C1—O1 | 126.9 (3) | N2—C8—C12 | 110.6 (2) |
O2—C1—C2 | 121.0 (2) | C9—C8—C12 | 105.2 (2) |
O1—C1—C2 | 112.1 (2) | N2—C8—C7 | 105.3 (2) |
N1—C2—C1 | 106.8 (2) | C9—C8—C7 | 114.9 (2) |
N1—C2—C3 | 110.7 (2) | C12—C8—C7 | 109.4 (2) |
C1—C2—C3 | 112.0 (2) | C10B—C9—C8 | 102.8 (8) |
N1—C2—C6 | 110.1 (2) | C10—C9—C8 | 108.3 (6) |
C1—C2—C6 | 112.2 (2) | C10—C9—H9A | 110.0 |
C3—C2—C6 | 105.1 (2) | C8—C9—H9A | 110.0 |
C4—C3—C2 | 106.2 (4) | C10—C9—H9B | 110.0 |
C2—C3—C4B | 101.7 (7) | C8—C9—H9B | 110.0 |
C4—C3—H3A | 110.5 | H9A—C9—H9B | 108.4 |
C2—C3—H3A | 110.5 | C9—C10—C11 | 105.6 (10) |
C4—C3—H3B | 110.5 | C9—C10—H10A | 110.6 |
C2—C3—H3B | 110.5 | C11—C10—H10A | 110.6 |
H3A—C3—H3B | 108.7 | C9—C10—H10B | 110.6 |
C3—C4—C5 | 98.6 (6) | C11—C10—H10B | 110.6 |
C3—C4—H4A | 112.0 | H10A—C10—H10B | 108.8 |
C5—C4—H4A | 112.0 | C12—C11—C10 | 108.0 (8) |
C3—C4—H4B | 112.0 | C12—C11—H11A | 110.1 |
C5—C4—H4B | 112.0 | C10—C11—H11A | 110.1 |
H4A—C4—H4B | 109.7 | C12—C11—H11B | 110.1 |
C6—C5—C4 | 105.9 (7) | C10—C11—H11B | 110.1 |
C6—C5—H5A | 110.6 | H11A—C11—H11B | 108.4 |
C4—C5—H5A | 110.6 | C9—C10B—C11B | 102.0 (10) |
C6—C5—H5B | 110.6 | C9—C10B—H10C | 111.4 |
C4—C5—H5B | 110.6 | C11B—C10B—H10C | 111.4 |
H5A—C5—H5B | 108.7 | C9—C10B—H10D | 111.4 |
C5B—C4B—C3 | 111.1 (15) | C11B—C10B—H10D | 111.4 |
C5B—C4B—H4B1 | 109.4 | H10C—C10B—H10D | 109.2 |
C3—C4B—H4B1 | 109.4 | C12—C11B—C10B | 99.5 (9) |
C5B—C4B—H4B2 | 109.4 | C12—C11B—H11C | 111.9 |
C3—C4B—H4B2 | 109.4 | C10B—C11B—H11C | 111.9 |
H4B1—C4B—H4B2 | 108.0 | C12—C11B—H11D | 111.9 |
C6—C5B—C4B | 97.3 (12) | C10B—C11B—H11D | 111.9 |
C6—C5B—H5B1 | 112.3 | H11C—C11B—H11D | 109.6 |
C4B—C5B—H5B1 | 112.3 | C11—C12—C8 | 107.0 (5) |
C6—C5B—H5B2 | 112.3 | C11B—C12—C8 | 105.4 (4) |
C4B—C5B—H5B2 | 112.3 | C11—C12—H12A | 110.3 |
H5B1—C5B—H5B2 | 109.9 | C8—C12—H12A | 110.3 |
C5B—C6—C2 | 110.4 (9) | C11—C12—H12B | 110.3 |
C5—C6—C2 | 104.3 (5) | C8—C12—H12B | 110.3 |
C5—C6—H6A | 110.9 | H12A—C12—H12B | 108.6 |
C2—C6—H6A | 110.9 | O6—C13—O5 | 125.3 (2) |
C5—C6—H6B | 110.9 | O6—C13—C14 | 122.8 (2) |
C2—C6—H6B | 110.9 | O5—C13—C14 | 111.9 (2) |
H6A—C6—H6B | 108.9 | O8—C14—O7 | 126.6 (2) |
C8—N2—H21 | 107.6 (19) | O8—C14—C13 | 118.7 (2) |
C8—N2—H22 | 109 (3) | O7—C14—C13 | 114.8 (2) |
H21—N2—H22 | 111 (3) | C13—O5—H55 | 111 (2) |
C8—N2—H23 | 116 (2) | H2W—O1W—H1W | 100 (4) |