Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624008064/op3032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624008064/op3032matrine-casup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624008064/op3032matrine-sasup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624008064/op3032matrine-hsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624008064/op3032matrine-casup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624008064/op3032matrine-sasup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624008064/op3032matrine-hsup7.cml |
CCDC references: 2362540; 2362541; 2362542
C15H25N2O+·C9H7O4−·1.5H2O | Dx = 1.312 Mg m−3 |
Mr = 455.54 | Ga Kα radiation, λ = 1.34139 Å |
Orthorhombic, P212121 | Cell parameters from 9998 reflections |
a = 8.1508 (4) Å | θ = 3.8–60.5° |
b = 11.0066 (5) Å | µ = 0.50 mm−1 |
c = 25.7084 (12) Å | T = 170 K |
V = 2306.37 (19) Å3 | Block, colourless |
Z = 4 | 0.05 × 0.04 × 0.03 mm |
F(000) = 980 |
Bruker D8 Venture diffractometer | 4863 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.059 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 60.7°, θmin = 3.8° |
Tmin = 0.699, Tmax = 0.752 | h = −10→10 |
43143 measured reflections | k = −14→14 |
5269 independent reflections | l = −33→33 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0585P)2 + 0.1825P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.097 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.17 e Å−3 |
5269 reflections | Δρmin = −0.26 e Å−3 |
316 parameters | Absolute structure: Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
6 restraints | Absolute structure parameter: 0.07 (7) |
Primary atom site location: dual |
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. Single-crystal X-ray diffraction (SCXRD) data were collected on a Bruker D8 Venture diffractometer (Bruker, Ettlingen, Germany) with Ga Kα (λ = 1.34139 Å) radiation. Using OLEX2, the crystal structure was solved using intrinsic phasing methods (SHELXT) and refined with full-matrix least-squares methods with anisotropic thermal parameters for all non-H atoms on F2 using the SHELXL package. Crystal data, data collection and structure refinement details are summarized in Table 1 and hydrogen bonding parameters detailed in Tables 2–4. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.5438 (3) | 0.53361 (16) | 0.49236 (6) | 0.0520 (5) | |
N1 | 0.53019 (19) | 0.92335 (13) | 0.34514 (6) | 0.0235 (3) | |
H1 | 0.438145 | 0.863396 | 0.346719 | 0.028* | |
C1 | 0.4718 (3) | 1.04146 (18) | 0.36834 (9) | 0.0344 (5) | |
H1A | 0.379672 | 1.073818 | 0.347434 | 0.041* | |
H1B | 0.562011 | 1.101697 | 0.367518 | 0.041* | |
N2 | 0.5827 (2) | 0.63595 (15) | 0.41774 (6) | 0.0270 (4) | |
C2 | 0.4164 (3) | 1.0225 (2) | 0.42375 (9) | 0.0397 (5) | |
H2A | 0.322513 | 0.965468 | 0.424327 | 0.048* | |
H2B | 0.379183 | 1.100876 | 0.438515 | 0.048* | |
C3 | 0.5556 (3) | 0.9716 (2) | 0.45698 (9) | 0.0395 (5) | |
H3A | 0.513707 | 0.953659 | 0.492298 | 0.047* | |
H3B | 0.643087 | 1.033512 | 0.460247 | 0.047* | |
C4 | 0.6281 (3) | 0.8558 (2) | 0.43348 (8) | 0.0309 (4) | |
H4 | 0.731778 | 0.837676 | 0.452771 | 0.037* | |
C5 | 0.6738 (2) | 0.87313 (17) | 0.37614 (7) | 0.0250 (4) | |
H5 | 0.764646 | 0.934034 | 0.374496 | 0.030* | |
C6 | 0.5756 (3) | 0.94248 (18) | 0.28915 (8) | 0.0302 (4) | |
H6A | 0.662769 | 1.004871 | 0.286806 | 0.036* | |
H6B | 0.478781 | 0.972556 | 0.269787 | 0.036* | |
C7 | 0.6356 (3) | 0.82540 (19) | 0.26464 (7) | 0.0295 (4) | |
H7A | 0.669002 | 0.841091 | 0.228224 | 0.035* | |
H7B | 0.545389 | 0.765222 | 0.264202 | 0.035* | |
C8 | 0.7805 (2) | 0.77397 (18) | 0.29480 (7) | 0.0275 (4) | |
H8A | 0.874499 | 0.830642 | 0.292171 | 0.033* | |
H8B | 0.813962 | 0.695566 | 0.279187 | 0.033* | |
C9 | 0.7374 (2) | 0.75436 (17) | 0.35245 (7) | 0.0242 (4) | |
H9 | 0.842413 | 0.734812 | 0.370713 | 0.029* | |
C10 | 0.6217 (2) | 0.64554 (17) | 0.36138 (7) | 0.0229 (4) | |
H10 | 0.517228 | 0.661228 | 0.342128 | 0.028* | |
C11 | 0.5140 (3) | 0.74717 (19) | 0.44099 (8) | 0.0317 (4) | |
H11A | 0.495806 | 0.733855 | 0.478635 | 0.038* | |
H11B | 0.406493 | 0.764998 | 0.424776 | 0.038* | |
C12 | 0.5834 (3) | 0.5327 (2) | 0.44574 (8) | 0.0328 (5) | |
C13 | 0.6315 (3) | 0.4153 (2) | 0.42007 (9) | 0.0377 (5) | |
H13A | 0.564376 | 0.348670 | 0.434773 | 0.045* | |
H13B | 0.747864 | 0.397825 | 0.428122 | 0.045* | |
C14 | 0.6092 (3) | 0.41761 (18) | 0.36135 (8) | 0.0309 (4) | |
H14A | 0.655963 | 0.343091 | 0.345694 | 0.037* | |
H14B | 0.491032 | 0.421340 | 0.352546 | 0.037* | |
C15 | 0.6965 (2) | 0.52851 (18) | 0.34053 (8) | 0.0287 (4) | |
H15A | 0.690221 | 0.528596 | 0.302070 | 0.034* | |
H15B | 0.813740 | 0.524829 | 0.350478 | 0.034* | |
O2 | −0.11594 (18) | 0.14923 (12) | 0.32599 (5) | 0.0266 (3) | |
O3 | −0.0428 (2) | 0.07081 (13) | 0.42002 (6) | 0.0364 (4) | |
H3 | −0.016 (4) | 0.055 (3) | 0.4504 (6) | 0.055* | |
O4 | 0.20784 (19) | 0.75778 (12) | 0.25842 (5) | 0.0313 (3) | |
O5 | 0.25683 (17) | 0.77954 (12) | 0.34258 (5) | 0.0268 (3) | |
C16 | 0.0296 (2) | 0.33722 (15) | 0.34039 (7) | 0.0200 (3) | |
H16 | 0.005098 | 0.364277 | 0.306176 | 0.024* | |
C17 | −0.0248 (2) | 0.22420 (16) | 0.35669 (7) | 0.0203 (3) | |
C18 | 0.0132 (2) | 0.18249 (16) | 0.40686 (7) | 0.0233 (4) | |
C19 | 0.1048 (2) | 0.25604 (17) | 0.44005 (7) | 0.0255 (4) | |
H19 | 0.130957 | 0.228449 | 0.474074 | 0.031* | |
C20 | 0.1583 (2) | 0.36992 (17) | 0.42352 (7) | 0.0228 (4) | |
H20 | 0.221194 | 0.419210 | 0.446392 | 0.027* | |
C21 | 0.1209 (2) | 0.41239 (15) | 0.37391 (7) | 0.0200 (3) | |
C22 | 0.1730 (2) | 0.53495 (16) | 0.35921 (7) | 0.0206 (3) | |
H22 | 0.228572 | 0.580354 | 0.385242 | 0.025* | |
C23 | 0.1516 (2) | 0.59053 (16) | 0.31343 (7) | 0.0210 (4) | |
H23 | 0.098384 | 0.548120 | 0.286022 | 0.025* | |
C24 | 0.2090 (2) | 0.71695 (16) | 0.30435 (7) | 0.0208 (4) | |
O6 | 0.1538 (2) | 0.01337 (14) | 0.28106 (7) | 0.0414 (4) | |
H2 | −0.140 (4) | 0.183 (3) | 0.2974 (7) | 0.062* | |
H6C | 0.159 (4) | −0.0640 (13) | 0.2867 (12) | 0.062* | |
H6D | 0.075 (3) | 0.030 (3) | 0.3032 (10) | 0.062* | |
O7 | 0.5728 (6) | 0.7344 (4) | 0.56539 (16) | 0.0626 (11) | 0.5 |
H7C | 0.611 (10) | 0.743 (7) | 0.5976 (13) | 0.094* | 0.5 |
H7D | 0.570 (12) | 0.663 (4) | 0.550 (3) | 0.094* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0879 (14) | 0.0412 (9) | 0.0267 (8) | 0.0028 (9) | 0.0087 (9) | 0.0119 (7) |
N1 | 0.0244 (7) | 0.0178 (7) | 0.0282 (8) | −0.0029 (6) | −0.0021 (6) | 0.0008 (6) |
C1 | 0.0350 (10) | 0.0192 (9) | 0.0490 (12) | 0.0007 (8) | −0.0026 (9) | −0.0057 (9) |
N2 | 0.0350 (9) | 0.0245 (8) | 0.0213 (7) | 0.0049 (7) | 0.0029 (6) | 0.0041 (6) |
C2 | 0.0413 (12) | 0.0279 (10) | 0.0497 (13) | 0.0023 (9) | 0.0032 (10) | −0.0133 (10) |
C3 | 0.0469 (13) | 0.0370 (11) | 0.0346 (11) | −0.0029 (10) | −0.0003 (10) | −0.0141 (9) |
C4 | 0.0347 (10) | 0.0341 (10) | 0.0239 (9) | 0.0013 (9) | −0.0058 (8) | −0.0046 (8) |
C5 | 0.0223 (8) | 0.0257 (9) | 0.0269 (9) | −0.0026 (7) | −0.0052 (7) | −0.0021 (7) |
C6 | 0.0291 (10) | 0.0296 (10) | 0.0319 (10) | −0.0049 (8) | −0.0018 (8) | 0.0098 (8) |
C7 | 0.0314 (10) | 0.0354 (10) | 0.0215 (9) | −0.0073 (8) | 0.0017 (8) | 0.0038 (8) |
C8 | 0.0255 (9) | 0.0302 (10) | 0.0269 (10) | −0.0022 (8) | 0.0050 (8) | 0.0022 (8) |
C9 | 0.0210 (8) | 0.0283 (9) | 0.0234 (9) | 0.0017 (7) | −0.0016 (7) | −0.0005 (7) |
C10 | 0.0242 (8) | 0.0247 (9) | 0.0199 (8) | 0.0038 (7) | 0.0001 (7) | 0.0024 (7) |
C11 | 0.0420 (11) | 0.0313 (10) | 0.0216 (8) | 0.0046 (9) | 0.0049 (8) | 0.0014 (8) |
C12 | 0.0373 (11) | 0.0328 (10) | 0.0284 (10) | 0.0008 (9) | −0.0009 (8) | 0.0083 (8) |
C13 | 0.0442 (12) | 0.0271 (10) | 0.0418 (12) | 0.0051 (9) | −0.0012 (10) | 0.0096 (9) |
C14 | 0.0303 (10) | 0.0245 (9) | 0.0379 (11) | 0.0027 (8) | 0.0028 (9) | 0.0002 (8) |
C15 | 0.0292 (9) | 0.0249 (9) | 0.0319 (10) | 0.0031 (8) | 0.0052 (8) | −0.0015 (8) |
O2 | 0.0328 (7) | 0.0199 (6) | 0.0271 (7) | −0.0060 (6) | −0.0074 (5) | −0.0001 (5) |
O3 | 0.0473 (9) | 0.0275 (7) | 0.0345 (7) | −0.0141 (7) | −0.0135 (7) | 0.0122 (6) |
O4 | 0.0403 (8) | 0.0267 (7) | 0.0270 (7) | −0.0099 (6) | −0.0092 (6) | 0.0077 (6) |
O5 | 0.0289 (6) | 0.0219 (6) | 0.0295 (7) | −0.0073 (5) | 0.0004 (5) | −0.0042 (5) |
C16 | 0.0214 (8) | 0.0201 (8) | 0.0184 (8) | 0.0010 (7) | −0.0012 (7) | 0.0010 (6) |
C17 | 0.0205 (8) | 0.0184 (8) | 0.0220 (8) | 0.0004 (7) | −0.0015 (7) | −0.0033 (6) |
C18 | 0.0259 (9) | 0.0173 (8) | 0.0266 (9) | −0.0008 (7) | −0.0007 (7) | 0.0033 (7) |
C19 | 0.0291 (9) | 0.0267 (9) | 0.0206 (8) | −0.0015 (8) | −0.0038 (7) | 0.0028 (7) |
C20 | 0.0250 (9) | 0.0222 (8) | 0.0212 (8) | −0.0015 (7) | −0.0020 (7) | −0.0026 (7) |
C21 | 0.0202 (8) | 0.0175 (8) | 0.0223 (8) | 0.0004 (7) | 0.0014 (7) | −0.0009 (7) |
C22 | 0.0200 (8) | 0.0184 (8) | 0.0235 (8) | −0.0014 (6) | −0.0012 (7) | −0.0024 (7) |
C23 | 0.0225 (8) | 0.0190 (8) | 0.0215 (8) | −0.0022 (7) | −0.0020 (7) | −0.0033 (7) |
C24 | 0.0163 (7) | 0.0180 (8) | 0.0281 (9) | 0.0008 (6) | −0.0029 (7) | 0.0011 (7) |
O6 | 0.0502 (10) | 0.0262 (7) | 0.0478 (9) | 0.0091 (7) | 0.0063 (8) | 0.0064 (7) |
O7 | 0.066 (3) | 0.067 (3) | 0.055 (2) | 0.013 (2) | −0.016 (2) | −0.013 (2) |
O1—C12 | 1.241 (3) | C11—H11A | 0.9900 |
N1—H1 | 1.0000 | C11—H11B | 0.9900 |
N1—C1 | 1.507 (2) | C12—C13 | 1.503 (3) |
N1—C5 | 1.520 (2) | C13—H13A | 0.9900 |
N1—C6 | 1.501 (2) | C13—H13B | 0.9900 |
C1—H1A | 0.9900 | C13—C14 | 1.521 (3) |
C1—H1B | 0.9900 | C14—H14A | 0.9900 |
C1—C2 | 1.509 (3) | C14—H14B | 0.9900 |
N2—C10 | 1.487 (2) | C14—C15 | 1.511 (3) |
N2—C11 | 1.473 (3) | C15—H15A | 0.9900 |
N2—C12 | 1.345 (3) | C15—H15B | 0.9900 |
C2—H2A | 0.9900 | O2—C17 | 1.362 (2) |
C2—H2B | 0.9900 | O2—H2 | 0.850 (13) |
C2—C3 | 1.527 (4) | O3—H3 | 0.831 (13) |
C3—H3A | 0.9900 | O3—C18 | 1.354 (2) |
C3—H3B | 0.9900 | O4—C24 | 1.263 (2) |
C3—C4 | 1.529 (3) | O5—C24 | 1.262 (2) |
C4—H4 | 1.0000 | C16—H16 | 0.9500 |
C4—C5 | 1.532 (3) | C16—C17 | 1.386 (2) |
C4—C11 | 1.526 (3) | C16—C21 | 1.407 (2) |
C5—H5 | 1.0000 | C17—C18 | 1.404 (2) |
C5—C9 | 1.533 (3) | C18—C19 | 1.393 (3) |
C6—H6A | 0.9900 | C19—H19 | 0.9500 |
C6—H6B | 0.9900 | C19—C20 | 1.394 (3) |
C6—C7 | 1.516 (3) | C20—H20 | 0.9500 |
C7—H7A | 0.9900 | C20—C21 | 1.392 (2) |
C7—H7B | 0.9900 | C21—C22 | 1.464 (2) |
C7—C8 | 1.522 (3) | C22—H22 | 0.9500 |
C8—H8A | 0.9900 | C22—C23 | 1.338 (2) |
C8—H8B | 0.9900 | C23—H23 | 0.9500 |
C8—C9 | 1.539 (3) | C23—C24 | 1.486 (2) |
C9—H9 | 1.0000 | O6—H6C | 0.865 (13) |
C9—C10 | 1.541 (3) | O6—H6D | 0.879 (13) |
C10—H10 | 1.0000 | O7—H7C | 0.890 (14) |
C10—C15 | 1.523 (3) | O7—H7D | 0.881 (14) |
C1—N1—H1 | 108.4 | N2—C10—H10 | 108.2 |
C1—N1—C5 | 110.43 (15) | N2—C10—C15 | 111.63 (15) |
C5—N1—H1 | 108.4 | C9—C10—H10 | 108.2 |
C6—N1—H1 | 108.4 | C15—C10—C9 | 111.10 (15) |
C6—N1—C1 | 109.65 (15) | C15—C10—H10 | 108.2 |
C6—N1—C5 | 111.35 (15) | N2—C11—C4 | 111.57 (17) |
N1—C1—H1A | 109.6 | N2—C11—H11A | 109.3 |
N1—C1—H1B | 109.6 | N2—C11—H11B | 109.3 |
N1—C1—C2 | 110.41 (17) | C4—C11—H11A | 109.3 |
H1A—C1—H1B | 108.1 | C4—C11—H11B | 109.3 |
C2—C1—H1A | 109.6 | H11A—C11—H11B | 108.0 |
C2—C1—H1B | 109.6 | O1—C12—N2 | 120.6 (2) |
C11—N2—C10 | 114.68 (14) | O1—C12—C13 | 119.92 (19) |
C12—N2—C10 | 125.48 (17) | N2—C12—C13 | 119.50 (17) |
C12—N2—C11 | 119.11 (16) | C12—C13—H13A | 109.0 |
C1—C2—H2A | 109.5 | C12—C13—H13B | 109.0 |
C1—C2—H2B | 109.5 | C12—C13—C14 | 112.99 (17) |
C1—C2—C3 | 110.9 (2) | H13A—C13—H13B | 107.8 |
H2A—C2—H2B | 108.1 | C14—C13—H13A | 109.0 |
C3—C2—H2A | 109.5 | C14—C13—H13B | 109.0 |
C3—C2—H2B | 109.5 | C13—C14—H14A | 110.1 |
C2—C3—H3A | 109.2 | C13—C14—H14B | 110.1 |
C2—C3—H3B | 109.2 | H14A—C14—H14B | 108.4 |
C2—C3—C4 | 111.84 (17) | C15—C14—C13 | 107.98 (17) |
H3A—C3—H3B | 107.9 | C15—C14—H14A | 110.1 |
C4—C3—H3A | 109.2 | C15—C14—H14B | 110.1 |
C4—C3—H3B | 109.2 | C10—C15—H15A | 109.3 |
C3—C4—H4 | 107.2 | C10—C15—H15B | 109.3 |
C3—C4—C5 | 111.70 (18) | C14—C15—C10 | 111.71 (16) |
C5—C4—H4 | 107.2 | C14—C15—H15A | 109.3 |
C11—C4—C3 | 111.57 (18) | C14—C15—H15B | 109.3 |
C11—C4—H4 | 107.2 | H15A—C15—H15B | 107.9 |
C11—C4—C5 | 111.55 (16) | C17—O2—H2 | 111 (2) |
N1—C5—C4 | 111.27 (16) | C18—O3—H3 | 110 (2) |
N1—C5—H5 | 107.7 | C17—C16—H16 | 119.6 |
N1—C5—C9 | 111.24 (14) | C17—C16—C21 | 120.79 (16) |
C4—C5—H5 | 107.7 | C21—C16—H16 | 119.6 |
C4—C5—C9 | 110.98 (16) | O2—C17—C16 | 122.90 (16) |
C9—C5—H5 | 107.7 | O2—C17—C18 | 117.04 (15) |
N1—C6—H6A | 109.4 | C16—C17—C18 | 120.06 (16) |
N1—C6—H6B | 109.4 | O3—C18—C17 | 116.88 (16) |
N1—C6—C7 | 111.04 (15) | O3—C18—C19 | 123.71 (17) |
H6A—C6—H6B | 108.0 | C19—C18—C17 | 119.40 (16) |
C7—C6—H6A | 109.4 | C18—C19—H19 | 119.9 |
C7—C6—H6B | 109.4 | C18—C19—C20 | 120.23 (17) |
C6—C7—H7A | 109.5 | C20—C19—H19 | 119.9 |
C6—C7—H7B | 109.5 | C19—C20—H20 | 119.6 |
C6—C7—C8 | 110.79 (16) | C21—C20—C19 | 120.84 (17) |
H7A—C7—H7B | 108.1 | C21—C20—H20 | 119.6 |
C8—C7—H7A | 109.5 | C16—C21—C22 | 122.49 (16) |
C8—C7—H7B | 109.5 | C20—C21—C16 | 118.66 (16) |
C7—C8—H8A | 109.3 | C20—C21—C22 | 118.82 (16) |
C7—C8—H8B | 109.3 | C21—C22—H22 | 116.2 |
C7—C8—C9 | 111.44 (15) | C23—C22—C21 | 127.62 (16) |
H8A—C8—H8B | 108.0 | C23—C22—H22 | 116.2 |
C9—C8—H8A | 109.3 | C22—C23—H23 | 119.2 |
C9—C8—H8B | 109.3 | C22—C23—C24 | 121.68 (16) |
C5—C9—C8 | 109.91 (16) | C24—C23—H23 | 119.2 |
C5—C9—H9 | 106.7 | O4—C24—C23 | 118.52 (16) |
C5—C9—C10 | 113.37 (15) | O5—C24—O4 | 122.41 (17) |
C8—C9—H9 | 106.7 | O5—C24—C23 | 119.07 (16) |
C8—C9—C10 | 113.11 (15) | H6C—O6—H6D | 98 (3) |
C10—C9—H9 | 106.7 | H7C—O7—H7D | 122 (8) |
N2—C10—C9 | 109.32 (15) | ||
O1—C12—C13—C14 | 156.6 (2) | C10—N2—C11—C4 | −56.8 (2) |
N1—C1—C2—C3 | 58.8 (2) | C10—N2—C12—O1 | −177.6 (2) |
N1—C5—C9—C8 | 54.9 (2) | C10—N2—C12—C13 | 1.9 (3) |
N1—C5—C9—C10 | −72.74 (19) | C11—N2—C10—C9 | 55.1 (2) |
N1—C6—C7—C8 | −56.9 (2) | C11—N2—C10—C15 | 178.40 (16) |
C1—N1—C5—C4 | 56.9 (2) | C11—N2—C12—O1 | −8.0 (3) |
C1—N1—C5—C9 | −178.75 (15) | C11—N2—C12—C13 | 171.6 (2) |
C1—N1—C6—C7 | 179.75 (16) | C11—C4—C5—N1 | 73.2 (2) |
C1—C2—C3—C4 | −54.3 (2) | C11—C4—C5—C9 | −51.3 (2) |
N2—C10—C15—C14 | 42.2 (2) | C12—N2—C10—C9 | −134.8 (2) |
N2—C12—C13—C14 | −22.9 (3) | C12—N2—C10—C15 | −11.5 (3) |
C2—C3—C4—C5 | 51.2 (3) | C12—N2—C11—C4 | 132.40 (19) |
C2—C3—C4—C11 | −74.5 (2) | C12—C13—C14—C15 | 52.2 (2) |
C3—C4—C5—N1 | −52.5 (2) | C13—C14—C15—C10 | −62.9 (2) |
C3—C4—C5—C9 | −176.91 (17) | O2—C17—C18—O3 | 0.7 (3) |
C3—C4—C11—N2 | 179.23 (16) | O2—C17—C18—C19 | −179.43 (17) |
C4—C5—C9—C8 | 179.40 (15) | O3—C18—C19—C20 | 179.83 (19) |
C4—C5—C9—C10 | 51.7 (2) | C16—C17—C18—O3 | −179.44 (17) |
C5—N1—C1—C2 | −60.2 (2) | C16—C17—C18—C19 | 0.4 (3) |
C5—N1—C6—C7 | 57.2 (2) | C16—C21—C22—C23 | −3.5 (3) |
C5—C4—C11—N2 | 53.5 (2) | C17—C16—C21—C20 | 1.3 (3) |
C5—C9—C10—N2 | −52.3 (2) | C17—C16—C21—C22 | −176.61 (16) |
C5—C9—C10—C15 | −175.90 (15) | C17—C18—C19—C20 | 0.0 (3) |
C6—N1—C1—C2 | 176.75 (17) | C18—C19—C20—C21 | 0.3 (3) |
C6—N1—C5—C4 | 179.01 (15) | C19—C20—C21—C16 | −0.9 (3) |
C6—N1—C5—C9 | −56.69 (19) | C19—C20—C21—C22 | 177.09 (17) |
C6—C7—C8—C9 | 56.1 (2) | C20—C21—C22—C23 | 178.56 (18) |
C7—C8—C9—C5 | −55.0 (2) | C21—C16—C17—O2 | 178.77 (16) |
C7—C8—C9—C10 | 72.8 (2) | C21—C16—C17—C18 | −1.1 (3) |
C8—C9—C10—N2 | −178.26 (15) | C21—C22—C23—C24 | 178.90 (16) |
C8—C9—C10—C15 | 58.1 (2) | C22—C23—C24—O4 | 169.44 (18) |
C9—C10—C15—C14 | 164.55 (16) | C22—C23—C24—O5 | −10.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5 | 1.00 | 1.75 | 2.734 (2) | 169 |
O3—H3···O1i | 0.83 (1) | 1.83 (2) | 2.626 (2) | 160 (3) |
O2—H2···O4ii | 0.85 (1) | 1.74 (1) | 2.5879 (19) | 174 (3) |
O6—H6C···O4iii | 0.87 (1) | 2.13 (2) | 2.906 (2) | 149 (3) |
O6—H6D···O2 | 0.88 (1) | 2.12 (2) | 2.899 (2) | 148 (3) |
O7—H7C···O5iv | 0.89 (1) | 1.96 (3) | 2.806 (4) | 158 (8) |
O7—H7D···O1 | 0.88 (1) | 2.06 (3) | 2.910 (5) | 161 (8) |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) x+1/2, −y+3/2, −z+1. |
C15H25N2O+·C7H5O3−·H2O | Dx = 1.294 Mg m−3 |
Mr = 404.49 | Ga Kα radiation, λ = 1.34139 Å |
Orthorhombic, P212121 | Cell parameters from 9983 reflections |
a = 9.2999 (4) Å | θ = 3.7–60.7° |
b = 12.7329 (5) Å | µ = 0.47 mm−1 |
c = 17.5349 (8) Å | T = 170 K |
V = 2076.39 (15) Å3 | Block, colourless |
Z = 4 | 0.09 × 0.07 × 0.06 mm |
F(000) = 872 |
Bruker D8 Venture diffractometer | 4568 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.038 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 60.8°, θmin = 3.7° |
Tmin = 0.704, Tmax = 0.752 | h = −12→12 |
33326 measured reflections | k = −16→16 |
4679 independent reflections | l = −22→22 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.2725P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.081 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.17 e Å−3 |
4679 reflections | Δρmin = −0.19 e Å−3 |
266 parameters | Absolute structure: Flack x determined using 1920 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.04 (4) |
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 | ||
O1 | 0.78504 (13) | 0.83322 (8) | 0.79102 (7) | 0.0378 (3) | |
O2 | 0.42780 (16) | 0.37680 (11) | 0.42017 (7) | 0.0486 (3) | |
H2 | 0.498189 | 0.359280 | 0.447368 | 0.073* | |
O3 | 0.61198 (13) | 0.39053 (9) | 0.52537 (7) | 0.0370 (3) | |
O4 | 0.59618 (11) | 0.51857 (9) | 0.61152 (6) | 0.0330 (2) | |
O5 | 0.63164 (13) | 1.02448 (11) | 0.77714 (7) | 0.0417 (3) | |
H5A | 0.572343 | 1.023439 | 0.815493 | 0.063* | |
H5B | 0.681952 | 0.967285 | 0.782106 | 0.063* | |
N1 | 0.84031 (13) | 0.42023 (9) | 0.66386 (7) | 0.0242 (2) | |
H1 | 0.751522 | 0.461616 | 0.652381 | 0.029* | |
N2 | 0.76049 (12) | 0.65766 (9) | 0.77737 (6) | 0.0227 (2) | |
C1 | 0.93159 (17) | 0.41605 (12) | 0.59299 (8) | 0.0299 (3) | |
H1A | 0.879508 | 0.377843 | 0.552310 | 0.036* | |
H1B | 1.021873 | 0.377689 | 0.603890 | 0.036* | |
C2 | 0.96626 (17) | 0.52600 (13) | 0.56625 (8) | 0.0314 (3) | |
H2A | 0.876041 | 0.563138 | 0.553168 | 0.038* | |
H2B | 1.026419 | 0.522431 | 0.519743 | 0.038* | |
C3 | 1.04610 (17) | 0.58705 (13) | 0.62809 (9) | 0.0330 (3) | |
H3A | 1.058403 | 0.660759 | 0.611350 | 0.040* | |
H3B | 1.142961 | 0.556245 | 0.635040 | 0.040* | |
C4 | 0.96595 (15) | 0.58541 (11) | 0.70476 (8) | 0.0261 (3) | |
H4 | 1.034485 | 0.611460 | 0.744427 | 0.031* | |
C5 | 0.92096 (15) | 0.47438 (11) | 0.72809 (8) | 0.0249 (3) | |
H5 | 1.010510 | 0.433186 | 0.738159 | 0.030* | |
C6 | 0.7968 (2) | 0.31069 (11) | 0.68560 (9) | 0.0350 (3) | |
H6A | 0.883973 | 0.267487 | 0.693605 | 0.042* | |
H6B | 0.740929 | 0.278935 | 0.643423 | 0.042* | |
C7 | 0.7068 (2) | 0.31005 (12) | 0.75768 (10) | 0.0380 (4) | |
H7A | 0.683779 | 0.236714 | 0.771940 | 0.046* | |
H7B | 0.615191 | 0.347556 | 0.748373 | 0.046* | |
C8 | 0.7879 (2) | 0.36310 (12) | 0.82286 (9) | 0.0351 (3) | |
H8A | 0.874846 | 0.321623 | 0.835212 | 0.042* | |
H8B | 0.725979 | 0.364788 | 0.868785 | 0.042* | |
C9 | 0.83204 (15) | 0.47536 (11) | 0.80185 (8) | 0.0250 (3) | |
H9 | 0.897536 | 0.500410 | 0.843259 | 0.030* | |
C10 | 0.70531 (15) | 0.55288 (10) | 0.79893 (7) | 0.0218 (2) | |
H10 | 0.637152 | 0.528916 | 0.758400 | 0.026* | |
C11 | 0.83793 (15) | 0.65995 (11) | 0.70437 (8) | 0.0249 (3) | |
H11A | 0.871964 | 0.732299 | 0.694289 | 0.030* | |
H11B | 0.771432 | 0.639869 | 0.662763 | 0.030* | |
C12 | 0.73395 (15) | 0.74889 (11) | 0.81362 (8) | 0.0272 (3) | |
C13 | 0.63792 (19) | 0.74690 (13) | 0.88284 (10) | 0.0355 (3) | |
H13A | 0.581027 | 0.812575 | 0.884501 | 0.043* | |
H13B | 0.698400 | 0.744472 | 0.929269 | 0.043* | |
C14 | 0.53621 (17) | 0.65391 (12) | 0.88326 (9) | 0.0307 (3) | |
H14A | 0.481426 | 0.652144 | 0.931651 | 0.037* | |
H14B | 0.467049 | 0.659752 | 0.840548 | 0.037* | |
C15 | 0.62470 (17) | 0.55474 (12) | 0.87496 (8) | 0.0278 (3) | |
H15A | 0.560623 | 0.492804 | 0.878144 | 0.033* | |
H15B | 0.694694 | 0.550399 | 0.917384 | 0.033* | |
C16 | 0.38377 (17) | 0.47386 (14) | 0.44007 (8) | 0.0352 (3) | |
C17 | 0.27822 (19) | 0.52336 (19) | 0.39600 (9) | 0.0466 (5) | |
H17 | 0.238162 | 0.488063 | 0.353260 | 0.056* | |
C18 | 0.2324 (2) | 0.62246 (19) | 0.41420 (11) | 0.0501 (5) | |
H18 | 0.160580 | 0.655142 | 0.383852 | 0.060* | |
C19 | 0.2893 (2) | 0.67601 (16) | 0.47634 (12) | 0.0463 (4) | |
H19 | 0.256764 | 0.744686 | 0.488617 | 0.056* | |
C20 | 0.39450 (19) | 0.62748 (13) | 0.52024 (9) | 0.0358 (3) | |
H20 | 0.433763 | 0.663655 | 0.562799 | 0.043* | |
C21 | 0.44349 (16) | 0.52690 (13) | 0.50307 (8) | 0.0293 (3) | |
C22 | 0.55864 (15) | 0.47501 (12) | 0.54960 (8) | 0.0279 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0386 (6) | 0.0233 (5) | 0.0516 (7) | −0.0050 (4) | 0.0145 (5) | −0.0070 (5) |
O2 | 0.0569 (8) | 0.0531 (8) | 0.0358 (6) | −0.0184 (6) | −0.0005 (6) | −0.0132 (6) |
O3 | 0.0369 (6) | 0.0372 (6) | 0.0367 (6) | −0.0018 (5) | 0.0031 (5) | −0.0040 (5) |
O4 | 0.0288 (5) | 0.0440 (6) | 0.0260 (5) | −0.0014 (5) | −0.0042 (4) | −0.0041 (4) |
O5 | 0.0391 (6) | 0.0493 (7) | 0.0367 (6) | 0.0085 (6) | 0.0071 (5) | 0.0098 (5) |
N1 | 0.0278 (6) | 0.0217 (5) | 0.0230 (5) | 0.0014 (4) | −0.0010 (5) | −0.0040 (4) |
N2 | 0.0251 (5) | 0.0213 (5) | 0.0216 (5) | 0.0004 (4) | 0.0017 (4) | −0.0015 (4) |
C1 | 0.0318 (7) | 0.0318 (7) | 0.0260 (7) | 0.0022 (6) | 0.0032 (6) | −0.0088 (5) |
C2 | 0.0321 (7) | 0.0365 (7) | 0.0257 (6) | −0.0035 (6) | 0.0060 (6) | −0.0061 (6) |
C3 | 0.0268 (7) | 0.0390 (8) | 0.0331 (7) | −0.0067 (6) | 0.0076 (6) | −0.0099 (6) |
C4 | 0.0218 (6) | 0.0305 (7) | 0.0259 (6) | −0.0026 (5) | 0.0001 (5) | −0.0067 (5) |
C5 | 0.0244 (6) | 0.0267 (6) | 0.0237 (6) | 0.0053 (5) | −0.0043 (5) | −0.0048 (5) |
C6 | 0.0507 (9) | 0.0200 (6) | 0.0341 (8) | −0.0005 (6) | 0.0018 (7) | −0.0035 (5) |
C7 | 0.0569 (10) | 0.0217 (6) | 0.0352 (8) | −0.0046 (7) | 0.0041 (8) | 0.0017 (6) |
C8 | 0.0520 (9) | 0.0248 (7) | 0.0286 (7) | 0.0084 (7) | 0.0007 (7) | 0.0051 (5) |
C9 | 0.0294 (6) | 0.0248 (6) | 0.0208 (6) | 0.0059 (5) | −0.0042 (5) | −0.0006 (5) |
C10 | 0.0243 (6) | 0.0205 (5) | 0.0205 (6) | 0.0006 (5) | −0.0012 (5) | −0.0002 (4) |
C11 | 0.0288 (6) | 0.0225 (6) | 0.0236 (6) | −0.0018 (5) | 0.0034 (5) | −0.0011 (5) |
C12 | 0.0238 (6) | 0.0251 (6) | 0.0326 (7) | 0.0013 (5) | 0.0014 (5) | −0.0049 (6) |
C13 | 0.0397 (8) | 0.0312 (7) | 0.0356 (8) | −0.0004 (7) | 0.0112 (7) | −0.0106 (6) |
C14 | 0.0291 (7) | 0.0342 (7) | 0.0287 (7) | 0.0020 (6) | 0.0072 (6) | −0.0005 (6) |
C15 | 0.0304 (7) | 0.0295 (6) | 0.0233 (6) | 0.0007 (6) | 0.0026 (5) | 0.0014 (5) |
C16 | 0.0340 (7) | 0.0491 (9) | 0.0224 (6) | −0.0189 (7) | 0.0026 (6) | −0.0011 (6) |
C17 | 0.0383 (9) | 0.0761 (13) | 0.0254 (7) | −0.0255 (9) | −0.0070 (7) | 0.0102 (8) |
C18 | 0.0362 (9) | 0.0725 (13) | 0.0415 (9) | −0.0119 (9) | −0.0087 (7) | 0.0262 (9) |
C19 | 0.0418 (9) | 0.0493 (10) | 0.0479 (10) | −0.0006 (8) | −0.0019 (8) | 0.0152 (8) |
C20 | 0.0357 (8) | 0.0404 (8) | 0.0314 (7) | −0.0056 (7) | −0.0030 (6) | 0.0032 (6) |
C21 | 0.0277 (6) | 0.0388 (8) | 0.0212 (6) | −0.0101 (6) | 0.0008 (5) | 0.0026 (5) |
C22 | 0.0255 (6) | 0.0350 (7) | 0.0231 (6) | −0.0086 (6) | 0.0032 (5) | 0.0006 (6) |
O1—C12 | 1.2392 (19) | C7—H7B | 0.9900 |
O2—H2 | 0.8400 | C7—C8 | 1.527 (2) |
O2—C16 | 1.348 (2) | C8—H8A | 0.9900 |
O3—C22 | 1.2584 (19) | C8—H8B | 0.9900 |
O4—C22 | 1.2683 (18) | C8—C9 | 1.532 (2) |
O5—H5A | 0.8698 | C9—H9 | 1.0000 |
O5—H5B | 0.8701 | C9—C10 | 1.5381 (18) |
N1—H1 | 1.0000 | C10—H10 | 1.0000 |
N1—C1 | 1.5060 (18) | C10—C15 | 1.5297 (18) |
N1—C5 | 1.5186 (17) | C11—H11A | 0.9900 |
N1—C6 | 1.5016 (18) | C11—H11B | 0.9900 |
N2—C10 | 1.4787 (17) | C12—C13 | 1.507 (2) |
N2—C11 | 1.4689 (17) | C13—H13A | 0.9900 |
N2—C12 | 1.3470 (18) | C13—H13B | 0.9900 |
C1—H1A | 0.9900 | C13—C14 | 1.516 (2) |
C1—H1B | 0.9900 | C14—H14A | 0.9900 |
C1—C2 | 1.511 (2) | C14—H14B | 0.9900 |
C2—H2A | 0.9900 | C14—C15 | 1.514 (2) |
C2—H2B | 0.9900 | C15—H15A | 0.9900 |
C2—C3 | 1.527 (2) | C15—H15B | 0.9900 |
C3—H3A | 0.9900 | C16—C17 | 1.399 (3) |
C3—H3B | 0.9900 | C16—C21 | 1.409 (2) |
C3—C4 | 1.537 (2) | C17—H17 | 0.9500 |
C4—H4 | 1.0000 | C17—C18 | 1.370 (3) |
C4—C5 | 1.530 (2) | C18—H18 | 0.9500 |
C4—C11 | 1.5226 (19) | C18—C19 | 1.390 (3) |
C5—H5 | 1.0000 | C19—H19 | 0.9500 |
C5—C9 | 1.5352 (18) | C19—C20 | 1.390 (3) |
C6—H6A | 0.9900 | C20—H20 | 0.9500 |
C6—H6B | 0.9900 | C20—C21 | 1.392 (2) |
C6—C7 | 1.516 (2) | C21—C22 | 1.500 (2) |
C7—H7A | 0.9900 | ||
C16—O2—H2 | 109.5 | C5—C9—C10 | 112.95 (11) |
H5A—O5—H5B | 104.5 | C8—C9—C5 | 109.84 (12) |
C1—N1—H1 | 108.5 | C8—C9—H9 | 106.6 |
C1—N1—C5 | 110.46 (11) | C8—C9—C10 | 113.65 (12) |
C5—N1—H1 | 108.5 | C10—C9—H9 | 106.6 |
C6—N1—H1 | 108.5 | N2—C10—C9 | 108.76 (11) |
C6—N1—C1 | 109.19 (11) | N2—C10—H10 | 108.3 |
C6—N1—C5 | 111.51 (11) | N2—C10—C15 | 112.27 (11) |
C11—N2—C10 | 114.26 (10) | C9—C10—H10 | 108.3 |
C12—N2—C10 | 126.43 (11) | C15—C10—C9 | 110.88 (11) |
C12—N2—C11 | 118.94 (12) | C15—C10—H10 | 108.3 |
N1—C1—H1A | 109.6 | N2—C11—C4 | 111.54 (11) |
N1—C1—H1B | 109.6 | N2—C11—H11A | 109.3 |
N1—C1—C2 | 110.09 (11) | N2—C11—H11B | 109.3 |
H1A—C1—H1B | 108.2 | C4—C11—H11A | 109.3 |
C2—C1—H1A | 109.6 | C4—C11—H11B | 109.3 |
C2—C1—H1B | 109.6 | H11A—C11—H11B | 108.0 |
C1—C2—H2A | 109.5 | O1—C12—N2 | 121.74 (13) |
C1—C2—H2B | 109.5 | O1—C12—C13 | 119.95 (13) |
C1—C2—C3 | 110.79 (13) | N2—C12—C13 | 118.30 (13) |
H2A—C2—H2B | 108.1 | C12—C13—H13A | 109.0 |
C3—C2—H2A | 109.5 | C12—C13—H13B | 109.0 |
C3—C2—H2B | 109.5 | C12—C13—C14 | 112.76 (12) |
C2—C3—H3A | 109.2 | H13A—C13—H13B | 107.8 |
C2—C3—H3B | 109.2 | C14—C13—H13A | 109.0 |
C2—C3—C4 | 112.23 (12) | C14—C13—H13B | 109.0 |
H3A—C3—H3B | 107.9 | C13—C14—H14A | 110.1 |
C4—C3—H3A | 109.2 | C13—C14—H14B | 110.1 |
C4—C3—H3B | 109.2 | H14A—C14—H14B | 108.4 |
C3—C4—H4 | 107.1 | C15—C14—C13 | 108.17 (13) |
C5—C4—C3 | 112.27 (12) | C15—C14—H14A | 110.1 |
C5—C4—H4 | 107.1 | C15—C14—H14B | 110.1 |
C11—C4—C3 | 111.52 (12) | C10—C15—H15A | 109.4 |
C11—C4—H4 | 107.1 | C10—C15—H15B | 109.4 |
C11—C4—C5 | 111.30 (11) | C14—C15—C10 | 111.28 (11) |
N1—C5—C4 | 110.87 (11) | C14—C15—H15A | 109.4 |
N1—C5—H5 | 107.7 | C14—C15—H15B | 109.4 |
N1—C5—C9 | 111.25 (11) | H15A—C15—H15B | 108.0 |
C4—C5—H5 | 107.7 | O2—C16—C17 | 118.89 (16) |
C4—C5—C9 | 111.41 (11) | O2—C16—C21 | 121.51 (16) |
C9—C5—H5 | 107.7 | C17—C16—C21 | 119.59 (18) |
N1—C6—H6A | 109.3 | C16—C17—H17 | 119.8 |
N1—C6—H6B | 109.3 | C18—C17—C16 | 120.30 (17) |
N1—C6—C7 | 111.44 (11) | C18—C17—H17 | 119.8 |
H6A—C6—H6B | 108.0 | C17—C18—H18 | 119.5 |
C7—C6—H6A | 109.3 | C17—C18—C19 | 121.08 (17) |
C7—C6—H6B | 109.3 | C19—C18—H18 | 119.5 |
C6—C7—H7A | 109.6 | C18—C19—H19 | 120.5 |
C6—C7—H7B | 109.6 | C20—C19—C18 | 118.9 (2) |
C6—C7—C8 | 110.43 (16) | C20—C19—H19 | 120.5 |
H7A—C7—H7B | 108.1 | C19—C20—H20 | 119.3 |
C8—C7—H7A | 109.6 | C19—C20—C21 | 121.31 (16) |
C8—C7—H7B | 109.6 | C21—C20—H20 | 119.3 |
C7—C8—H8A | 109.3 | C16—C21—C22 | 119.80 (16) |
C7—C8—H8B | 109.3 | C20—C21—C16 | 118.78 (15) |
C7—C8—C9 | 111.41 (12) | C20—C21—C22 | 121.42 (13) |
H8A—C8—H8B | 108.0 | O3—C22—O4 | 123.67 (15) |
C9—C8—H8A | 109.3 | O3—C22—C21 | 118.32 (13) |
C9—C8—H8B | 109.3 | O4—C22—C21 | 118.01 (14) |
C5—C9—H9 | 106.6 | ||
O1—C12—C13—C14 | 155.09 (15) | C7—C8—C9—C10 | 71.83 (17) |
O2—C16—C17—C18 | −179.23 (15) | C8—C9—C10—N2 | −179.36 (11) |
O2—C16—C21—C20 | 179.33 (14) | C8—C9—C10—C15 | 56.72 (15) |
O2—C16—C21—C22 | −0.1 (2) | C9—C10—C15—C14 | 160.17 (12) |
N1—C1—C2—C3 | 59.02 (16) | C10—N2—C11—C4 | −58.51 (14) |
N1—C5—C9—C8 | 55.17 (15) | C10—N2—C12—O1 | −179.83 (13) |
N1—C5—C9—C10 | −72.85 (14) | C10—N2—C12—C13 | −0.6 (2) |
N1—C6—C7—C8 | −56.48 (19) | C11—N2—C10—C9 | 57.32 (14) |
N2—C10—C15—C14 | 38.29 (16) | C11—N2—C10—C15 | −179.59 (11) |
N2—C12—C13—C14 | −24.2 (2) | C11—N2—C12—O1 | −7.2 (2) |
C1—N1—C5—C4 | 57.78 (14) | C11—N2—C12—C13 | 172.08 (13) |
C1—N1—C5—C9 | −177.64 (10) | C11—C4—C5—N1 | 74.28 (14) |
C1—N1—C6—C7 | 178.91 (14) | C11—C4—C5—C9 | −50.21 (15) |
C1—C2—C3—C4 | −52.93 (18) | C12—N2—C10—C9 | −129.75 (14) |
C2—C3—C4—C5 | 49.45 (18) | C12—N2—C10—C15 | −6.66 (19) |
C2—C3—C4—C11 | −76.23 (16) | C12—N2—C11—C4 | 127.99 (13) |
C3—C4—C5—N1 | −51.53 (15) | C12—C13—C14—C15 | 54.72 (17) |
C3—C4—C5—C9 | −176.02 (11) | C13—C14—C15—C10 | −62.32 (16) |
C3—C4—C11—N2 | 179.46 (11) | C16—C17—C18—C19 | 0.1 (3) |
C4—C5—C9—C8 | 179.45 (12) | C16—C21—C22—O3 | 8.9 (2) |
C4—C5—C9—C10 | 51.42 (15) | C16—C21—C22—O4 | −170.70 (13) |
C5—N1—C1—C2 | −61.78 (15) | C17—C16—C21—C20 | 0.6 (2) |
C5—N1—C6—C7 | 56.56 (18) | C17—C16—C21—C22 | −178.83 (13) |
C5—C4—C11—N2 | 53.23 (15) | C17—C18—C19—C20 | 0.1 (3) |
C5—C9—C10—N2 | −53.35 (14) | C18—C19—C20—C21 | 0.0 (3) |
C5—C9—C10—C15 | −177.27 (11) | C19—C20—C21—C16 | −0.4 (2) |
C6—N1—C1—C2 | 175.24 (13) | C19—C20—C21—C22 | 179.03 (15) |
C6—N1—C5—C4 | 179.39 (11) | C20—C21—C22—O3 | −170.51 (14) |
C6—N1—C5—C9 | −56.03 (15) | C20—C21—C22—O4 | 9.9 (2) |
C6—C7—C8—C9 | 56.54 (18) | C21—C16—C17—C18 | −0.4 (2) |
C7—C8—C9—C5 | −55.81 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.77 | 2.5233 (19) | 147 |
O5—H5A···O4i | 0.87 | 2.02 | 2.8820 (16) | 169 |
O5—H5B···O1 | 0.87 | 1.96 | 2.8329 (17) | 176 |
N1—H1···O4 | 1.00 | 1.77 | 2.7505 (17) | 167 |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
C15H24N2O·1.75H2O | Dx = 1.231 Mg m−3 |
Mr = 279.89 | Ga Kα radiation, λ = 1.34139 Å |
Tetragonal, P43212 | Cell parameters from 9770 reflections |
a = 11.7364 (3) Å | θ = 3.7–60.5° |
c = 21.9295 (9) Å | µ = 0.43 mm−1 |
V = 3020.6 (2) Å3 | T = 170 K |
Z = 8 | Block, colourless |
F(000) = 1228 | 0.09 × 0.08 × 0.06 mm |
Bruker D8 Venture diffractometer | 3335 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.042 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 60.8°, θmin = 3.7° |
Tmin = 0.698, Tmax = 0.752 | h = −15→15 |
49632 measured reflections | k = −14→15 |
3473 independent reflections | l = −28→28 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.5768P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.35 e Å−3 |
3473 reflections | Δρmin = −0.23 e Å−3 |
192 parameters | Absolute structure: Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: −0.01 (6) |
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) | |
O1 | 0.63861 (10) | 0.70536 (11) | 0.64097 (5) | 0.0310 (3) | |
O2 | 0.25063 (14) | 0.96006 (12) | 0.53692 (7) | 0.0412 (3) | |
H2C | 0.214514 | 0.905173 | 0.557856 | 0.062* | |
H2D | 0.287433 | 0.918759 | 0.509271 | 0.062* | |
O3 | 0.1771 (4) | 1.1412 (5) | 0.4712 (2) | 0.0987 (17) | 0.5 |
H3C | 0.105070 | 1.162701 | 0.465220 | 0.148* | 0.5 |
H3D | 0.186460 | 1.088110 | 0.498270 | 0.148* | 0.5 |
O4 | 0.3131 (5) | 1.3131 (5) | 0.500000 | 0.117 (3) | 0.5 |
H4A | 0.289350 | 1.350300 | 0.468121 | 0.176* | 0.25 |
H4B | 0.253201 | 1.280849 | 0.515650 | 0.176* | 0.25 |
N1 | 0.35870 (12) | 0.84195 (12) | 0.44148 (6) | 0.0254 (3) | |
N2 | 0.49194 (11) | 0.71006 (11) | 0.57406 (5) | 0.0208 (3) | |
C1 | 0.40419 (16) | 0.94079 (16) | 0.40753 (8) | 0.0336 (4) | |
H1A | 0.344535 | 1.000163 | 0.404530 | 0.040* | |
H1B | 0.424411 | 0.916764 | 0.365634 | 0.040* | |
C2 | 0.50831 (17) | 0.99034 (16) | 0.43835 (8) | 0.0342 (4) | |
H2A | 0.487252 | 1.019445 | 0.479195 | 0.041* | |
H2B | 0.537723 | 1.054976 | 0.413985 | 0.041* | |
C3 | 0.60086 (15) | 0.89975 (16) | 0.44473 (8) | 0.0305 (4) | |
H3A | 0.630356 | 0.879702 | 0.403818 | 0.037* | |
H3B | 0.664846 | 0.930947 | 0.468948 | 0.037* | |
C4 | 0.55521 (13) | 0.79272 (14) | 0.47577 (7) | 0.0234 (3) | |
H4 | 0.614007 | 0.731703 | 0.470997 | 0.028* | |
C5 | 0.44555 (14) | 0.75018 (14) | 0.44537 (6) | 0.0238 (3) | |
H5 | 0.464608 | 0.725312 | 0.402969 | 0.029* | |
C6 | 0.25572 (16) | 0.80021 (18) | 0.40986 (8) | 0.0355 (4) | |
H6A | 0.276142 | 0.777110 | 0.367844 | 0.043* | |
H6B | 0.199362 | 0.862766 | 0.407092 | 0.043* | |
C7 | 0.20234 (16) | 0.69976 (17) | 0.44275 (9) | 0.0358 (4) | |
H7A | 0.135245 | 0.672375 | 0.419651 | 0.043* | |
H7B | 0.176392 | 0.723771 | 0.483740 | 0.043* | |
C8 | 0.28963 (16) | 0.60356 (16) | 0.44880 (9) | 0.0337 (4) | |
H8A | 0.308776 | 0.573702 | 0.407839 | 0.040* | |
H8B | 0.256455 | 0.540519 | 0.472975 | 0.040* | |
C9 | 0.39828 (13) | 0.64686 (14) | 0.48012 (7) | 0.0244 (3) | |
H9 | 0.456334 | 0.584830 | 0.476626 | 0.029* | |
C10 | 0.38189 (13) | 0.67060 (13) | 0.54886 (7) | 0.0222 (3) | |
H10 | 0.325463 | 0.733922 | 0.553222 | 0.027* | |
C11 | 0.53762 (13) | 0.81170 (13) | 0.54397 (7) | 0.0227 (3) | |
H11A | 0.611311 | 0.832346 | 0.562950 | 0.027* | |
H11B | 0.484356 | 0.876102 | 0.550080 | 0.027* | |
C12 | 0.54387 (13) | 0.66987 (13) | 0.62436 (7) | 0.0223 (3) | |
C13 | 0.48330 (15) | 0.58008 (15) | 0.66176 (8) | 0.0294 (4) | |
H13A | 0.497952 | 0.594392 | 0.705554 | 0.035* | |
H13B | 0.515119 | 0.504308 | 0.651576 | 0.035* | |
C14 | 0.35597 (15) | 0.57851 (15) | 0.65091 (8) | 0.0314 (4) | |
H14A | 0.321211 | 0.649850 | 0.666214 | 0.038* | |
H14B | 0.320937 | 0.513558 | 0.672782 | 0.038* | |
C15 | 0.33563 (15) | 0.56709 (15) | 0.58279 (8) | 0.0307 (4) | |
H15A | 0.252904 | 0.559686 | 0.574898 | 0.037* | |
H15B | 0.373619 | 0.497351 | 0.567567 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0276 (6) | 0.0382 (7) | 0.0273 (5) | −0.0056 (5) | −0.0083 (5) | 0.0061 (5) |
O2 | 0.0506 (9) | 0.0319 (7) | 0.0412 (7) | 0.0041 (6) | 0.0191 (6) | −0.0013 (6) |
O3 | 0.065 (3) | 0.125 (4) | 0.107 (3) | 0.045 (3) | 0.030 (2) | 0.076 (3) |
O4 | 0.139 (5) | 0.139 (5) | 0.073 (4) | −0.069 (6) | −0.030 (4) | 0.030 (4) |
N1 | 0.0248 (7) | 0.0290 (7) | 0.0223 (6) | 0.0074 (5) | −0.0017 (5) | 0.0026 (5) |
N2 | 0.0197 (6) | 0.0219 (6) | 0.0210 (5) | −0.0021 (4) | −0.0012 (5) | 0.0022 (5) |
C1 | 0.0375 (9) | 0.0371 (10) | 0.0262 (8) | 0.0103 (7) | 0.0024 (7) | 0.0100 (7) |
C2 | 0.0415 (10) | 0.0296 (9) | 0.0316 (8) | 0.0019 (8) | 0.0068 (7) | 0.0094 (7) |
C3 | 0.0286 (8) | 0.0355 (9) | 0.0272 (8) | −0.0009 (7) | 0.0060 (6) | 0.0070 (7) |
C4 | 0.0205 (7) | 0.0272 (8) | 0.0223 (7) | 0.0039 (6) | 0.0018 (6) | 0.0024 (6) |
C5 | 0.0243 (8) | 0.0277 (8) | 0.0194 (6) | 0.0073 (6) | −0.0001 (6) | −0.0026 (6) |
C6 | 0.0304 (9) | 0.0446 (10) | 0.0313 (8) | 0.0097 (8) | −0.0107 (7) | −0.0027 (8) |
C7 | 0.0248 (8) | 0.0411 (10) | 0.0415 (9) | 0.0034 (8) | −0.0130 (7) | −0.0070 (8) |
C8 | 0.0310 (9) | 0.0329 (9) | 0.0371 (9) | 0.0015 (7) | −0.0112 (7) | −0.0086 (7) |
C9 | 0.0222 (7) | 0.0234 (7) | 0.0276 (7) | 0.0035 (6) | −0.0044 (6) | −0.0045 (6) |
C10 | 0.0177 (7) | 0.0219 (7) | 0.0271 (7) | −0.0004 (5) | −0.0025 (6) | 0.0002 (6) |
C11 | 0.0233 (7) | 0.0236 (7) | 0.0212 (7) | −0.0041 (6) | −0.0012 (5) | 0.0025 (6) |
C12 | 0.0226 (7) | 0.0247 (7) | 0.0195 (6) | 0.0016 (6) | 0.0007 (6) | 0.0004 (6) |
C13 | 0.0300 (8) | 0.0317 (8) | 0.0265 (7) | 0.0000 (7) | 0.0022 (6) | 0.0083 (7) |
C14 | 0.0271 (8) | 0.0311 (9) | 0.0360 (9) | −0.0039 (7) | 0.0078 (7) | 0.0076 (7) |
C15 | 0.0261 (8) | 0.0280 (8) | 0.0382 (9) | −0.0071 (6) | −0.0002 (7) | 0.0042 (7) |
O1—C12 | 1.242 (2) | C5—H5 | 1.0000 |
O2—H2C | 0.90 (3) | C5—C9 | 1.536 (2) |
O2—H2D | 0.8882 | C6—H6A | 0.9900 |
O3—H3C | 0.892 (4) | C6—H6B | 0.9900 |
O3—H3D | 0.868 (4) | C6—C7 | 1.517 (3) |
O4—H4A | 0.8701 (10) | C7—H7A | 0.9900 |
O4—H4Ai | 0.8700 (10) | C7—H7B | 0.9900 |
O4—H4B | 0.869 (7) | C7—C8 | 1.530 (3) |
O4—H4Bi | 0.869 (7) | C8—H8A | 0.9900 |
N1—C1 | 1.478 (2) | C8—H8B | 0.9900 |
N1—C5 | 1.485 (2) | C8—C9 | 1.535 (2) |
N1—C6 | 1.477 (2) | C9—H9 | 1.0000 |
N2—C10 | 1.4793 (19) | C9—C10 | 1.545 (2) |
N2—C11 | 1.4648 (19) | C10—H10 | 1.0000 |
N2—C12 | 1.3456 (19) | C10—C15 | 1.525 (2) |
C1—H1A | 0.9900 | C11—H11A | 0.9900 |
C1—H1B | 0.9900 | C11—H11B | 0.9900 |
C1—C2 | 1.513 (3) | C12—C13 | 1.513 (2) |
C2—H2A | 0.9900 | C13—H13A | 0.9900 |
C2—H2B | 0.9900 | C13—H13B | 0.9900 |
C2—C3 | 1.526 (3) | C13—C14 | 1.513 (2) |
C3—H3A | 0.9900 | C14—H14A | 0.9900 |
C3—H3B | 0.9900 | C14—H14B | 0.9900 |
C3—C4 | 1.526 (2) | C14—C15 | 1.519 (3) |
C4—H4 | 1.0000 | C15—H15A | 0.9900 |
C4—C5 | 1.533 (2) | C15—H15B | 0.9900 |
C4—C11 | 1.526 (2) | ||
H2C—O2—H2D | 100.8 | C6—C7—H7B | 109.7 |
H3C—O3—H3D | 115.1 (5) | C6—C7—C8 | 109.76 (16) |
H4A—O4—H4Ai | 165.2 (10) | H7A—C7—H7B | 108.2 |
H4Ai—O4—H4Bi | 106.1 (5) | C8—C7—H7A | 109.7 |
H4A—O4—H4Bi | 87.1 (4) | C8—C7—H7B | 109.7 |
H4A—O4—H4B | 106.1 (5) | C7—C8—H8A | 109.5 |
H4B—O4—H4Ai | 87.1 (4) | C7—C8—H8B | 109.5 |
H4B—O4—H4Bi | 56.7 (5) | C7—C8—C9 | 110.53 (14) |
C1—N1—C5 | 110.50 (13) | H8A—C8—H8B | 108.1 |
C6—N1—C1 | 108.64 (13) | C9—C8—H8A | 109.5 |
C6—N1—C5 | 110.37 (14) | C9—C8—H8B | 109.5 |
C11—N2—C10 | 113.97 (11) | C5—C9—H9 | 106.9 |
C12—N2—C10 | 126.29 (13) | C5—C9—C10 | 112.74 (13) |
C12—N2—C11 | 119.28 (13) | C8—C9—C5 | 109.85 (14) |
N1—C1—H1A | 109.3 | C8—C9—H9 | 106.9 |
N1—C1—H1B | 109.3 | C8—C9—C10 | 113.13 (14) |
N1—C1—C2 | 111.63 (14) | C10—C9—H9 | 106.9 |
H1A—C1—H1B | 108.0 | N2—C10—C9 | 108.19 (12) |
C2—C1—H1A | 109.3 | N2—C10—H10 | 108.0 |
C2—C1—H1B | 109.3 | N2—C10—C15 | 112.22 (13) |
C1—C2—H2A | 109.6 | C9—C10—H10 | 108.0 |
C1—C2—H2B | 109.6 | C15—C10—C9 | 112.14 (13) |
C1—C2—C3 | 110.37 (15) | C15—C10—H10 | 108.0 |
H2A—C2—H2B | 108.1 | N2—C11—C4 | 111.85 (13) |
C3—C2—H2A | 109.6 | N2—C11—H11A | 109.2 |
C3—C2—H2B | 109.6 | N2—C11—H11B | 109.2 |
C2—C3—H3A | 109.4 | C4—C11—H11A | 109.2 |
C2—C3—H3B | 109.4 | C4—C11—H11B | 109.2 |
H3A—C3—H3B | 108.0 | H11A—C11—H11B | 107.9 |
C4—C3—C2 | 111.38 (14) | O1—C12—N2 | 121.90 (14) |
C4—C3—H3A | 109.4 | O1—C12—C13 | 119.69 (14) |
C4—C3—H3B | 109.4 | N2—C12—C13 | 118.41 (14) |
C3—C4—H4 | 107.5 | C12—C13—H13A | 109.0 |
C3—C4—C5 | 111.64 (13) | C12—C13—H13B | 109.0 |
C3—C4—C11 | 111.38 (13) | C12—C13—C14 | 112.78 (14) |
C5—C4—H4 | 107.5 | H13A—C13—H13B | 107.8 |
C11—C4—H4 | 107.5 | C14—C13—H13A | 109.0 |
C11—C4—C5 | 111.10 (12) | C14—C13—H13B | 109.0 |
N1—C5—C4 | 111.41 (13) | C13—C14—H14A | 110.1 |
N1—C5—H5 | 108.2 | C13—C14—H14B | 110.1 |
N1—C5—C9 | 110.69 (13) | C13—C14—C15 | 108.12 (14) |
C4—C5—H5 | 108.2 | H14A—C14—H14B | 108.4 |
C4—C5—C9 | 110.16 (12) | C15—C14—H14A | 110.1 |
C9—C5—H5 | 108.2 | C15—C14—H14B | 110.1 |
N1—C6—H6A | 109.2 | C10—C15—H15A | 109.5 |
N1—C6—H6B | 109.2 | C10—C15—H15B | 109.5 |
N1—C6—C7 | 111.87 (14) | C14—C15—C10 | 110.72 (14) |
H6A—C6—H6B | 107.9 | C14—C15—H15A | 109.5 |
C7—C6—H6A | 109.2 | C14—C15—H15B | 109.5 |
C7—C6—H6B | 109.2 | H15A—C15—H15B | 108.1 |
C6—C7—H7A | 109.7 | ||
O1—C12—C13—C14 | 157.96 (15) | C6—N1—C1—C2 | 178.41 (14) |
N1—C1—C2—C3 | 57.83 (18) | C6—N1—C5—C4 | 177.75 (12) |
N1—C5—C9—C8 | 57.27 (16) | C6—N1—C5—C9 | −59.31 (16) |
N1—C5—C9—C10 | −69.89 (16) | C6—C7—C8—C9 | 55.0 (2) |
N1—C6—C7—C8 | −57.47 (19) | C7—C8—C9—C5 | −55.19 (19) |
N2—C10—C15—C14 | 39.71 (19) | C7—C8—C9—C10 | 71.76 (19) |
N2—C12—C13—C14 | −21.2 (2) | C8—C9—C10—N2 | 179.23 (13) |
C1—N1—C5—C4 | 57.57 (16) | C8—C9—C10—C15 | 54.94 (18) |
C1—N1—C5—C9 | −179.49 (12) | C9—C10—C15—C14 | 161.74 (14) |
C1—N1—C6—C7 | −178.87 (15) | C10—N2—C11—C4 | −58.37 (16) |
C1—C2—C3—C4 | −52.81 (19) | C10—N2—C12—O1 | 177.29 (14) |
C2—C3—C4—C5 | 50.99 (18) | C10—N2—C12—C13 | −3.6 (2) |
C2—C3—C4—C11 | −73.86 (18) | C11—N2—C10—C9 | 57.60 (16) |
C3—C4—C5—N1 | −53.37 (17) | C11—N2—C10—C15 | −178.16 (13) |
C3—C4—C5—C9 | −176.61 (13) | C11—N2—C12—O1 | −11.0 (2) |
C3—C4—C11—N2 | 179.02 (13) | C11—N2—C12—C13 | 168.13 (14) |
C4—C5—C9—C8 | −179.07 (13) | C11—C4—C5—N1 | 71.63 (16) |
C4—C5—C9—C10 | 53.77 (16) | C11—C4—C5—C9 | −51.61 (16) |
C5—N1—C1—C2 | −60.38 (18) | C12—N2—C10—C9 | −130.31 (15) |
C5—N1—C6—C7 | 59.84 (18) | C12—N2—C10—C15 | −6.1 (2) |
C5—C4—C11—N2 | 53.87 (16) | C12—N2—C11—C4 | 128.94 (14) |
C5—C9—C10—N2 | −55.36 (16) | C12—C13—C14—C15 | 53.73 (19) |
C5—C9—C10—C15 | −179.65 (13) | C13—C14—C15—C10 | −63.65 (18) |
Symmetry code: (i) y−1, x+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2C···O1ii | 0.90 (3) | 1.93 (3) | 2.8282 (19) | 175 (3) |
O2—H2D···N1 | 0.89 | 1.93 | 2.8125 (19) | 173 |
O3—H3C···O2i | 0.892 (4) | 1.9909 (14) | 2.858 (4) | 163.8 (4) |
O3—H3D···O2 | 0.868 (4) | 1.8826 (15) | 2.710 (4) | 158.8 (3) |
O4—H4B···O3i | 0.869 (7) | 1.815 (6) | 2.648 (9) | 160.2 (3) |
Symmetry codes: (i) y−1, x+1, −z+1; (ii) x−1/2, −y+3/2, −z+5/4. |
Torsion angle | Matrin–CA | Matrin–SA | Matrin–H | 2322345 | 2177201 | 2177196 |
O1—C12—N2—C11 | -7.9 (3) | -7.2 (2) | -11.0 (2) | -12.6 (5) | 8.1 (3) | 18.7 (4) |
C14—C15—C10—C9 | 165.56 (16) | 160.17 (12) | 161.73 (13) | 172.2 (3) | 68.2 (2) | 76.3 (3) |