Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617001516/ky3108sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617001516/ky3108Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617001516/ky3108IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617001516/ky3108IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617001516/ky3108IVsup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617001516/ky3108Isup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617001516/ky3108IIsup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617001516/ky3108IIIsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617001516/ky3108IVsup9.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617001516/ky3108sup10.pdf |
CCDC references: 1530068; 1530067; 1530066; 1530065
Data collection: CrystalClear-SM Expert (Rigaku, 2011) for (I), (II), (III); APEX3 (Bruker, 2016) for fh24. Cell refinement: CrysAlis PRO (Agilent, 2014) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II), (III); APEX3 (Bruker, 2016) for fh24. Data reduction: CrysAlis PRO (Agilent, 2014) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II), (III); SAINT (Bruker, 2015) for fh24. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: Mercury (Macrae et al., 2008) for (I), (II), (III); OLEX2 (Macrae et al., 2008) for fh24. Software used to prepare material for publication: enCIFer (Allen et al., 2004) for (I); enCIFer (Allen et al., 2004 for (II), (III); OLEX2 (Dolomanov et al., 2009) for fh24.
C20H21N2OP | Dx = 1.273 Mg m−3 |
Mr = 336.36 | Melting point: 402 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 11918 reflections |
a = 17.4366 (4) Å | θ = 2.1–29.2° |
b = 22.7127 (5) Å | µ = 0.17 mm−1 |
c = 8.8598 (2) Å | T = 120 K |
V = 3508.77 (14) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.20 × 0.10 mm |
F(000) = 1424 |
Rigaku Saturn724+ (2x2 bin mode) diffractometer | 6363 independent reflections |
Radiation source: Rotating Anode | 5746 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.047 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 25.4°, θmin = 2.9° |
profile data from ω–scans | h = −21→20 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −27→26 |
Tmin = 0.885, Tmax = 1.000 | l = −10→10 |
21879 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)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.3795P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6363 reflections | Δρmax = 0.29 e Å−3 |
447 parameters | Δρmin = −0.25 e Å−3 |
5 restraints | Absolute structure: Flack (1983), 2931 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (7) |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.20191 (3) | 0.72514 (2) | 0.71389 (7) | 0.01958 (12) | |
O1 | 0.17778 (9) | 0.74673 (7) | 0.56429 (17) | 0.0264 (4) | |
N1 | 0.16342 (10) | 0.66156 (8) | 0.7592 (2) | 0.0228 (4) | |
H1N | 0.1895 (12) | 0.6443 (10) | 0.832 (2) | 0.027* | |
N2 | 0.17917 (10) | 0.77043 (8) | 0.8523 (2) | 0.0226 (4) | |
H2N | 0.1497 (11) | 0.7566 (11) | 0.923 (2) | 0.027* | |
C1 | 0.30324 (10) | 0.71086 (8) | 0.7218 (3) | 0.0206 (4) | |
C2 | 0.33453 (12) | 0.67063 (9) | 0.6187 (2) | 0.0229 (5) | |
H2B | 0.3023 | 0.6525 | 0.5459 | 0.028* | |
C3 | 0.41163 (12) | 0.65715 (10) | 0.6220 (3) | 0.0258 (5) | |
H3A | 0.4323 | 0.6294 | 0.5529 | 0.031* | |
C4 | 0.45872 (12) | 0.68430 (9) | 0.7268 (3) | 0.0280 (5) | |
H4A | 0.5119 | 0.6751 | 0.7292 | 0.034* | |
C5 | 0.42888 (12) | 0.72474 (10) | 0.8281 (3) | 0.0273 (5) | |
H5A | 0.4617 | 0.7435 | 0.8989 | 0.033* | |
C6 | 0.35139 (12) | 0.73787 (10) | 0.8266 (3) | 0.0239 (5) | |
H6A | 0.3310 | 0.7653 | 0.8969 | 0.029* | |
C7 | 0.08007 (12) | 0.65341 (10) | 0.7576 (3) | 0.0288 (5) | |
H7A | 0.0554 | 0.6916 | 0.7339 | 0.035* | |
H7B | 0.0631 | 0.6415 | 0.8597 | 0.035* | |
C8 | 0.05302 (12) | 0.60801 (10) | 0.6452 (3) | 0.0256 (5) | |
C9 | −0.02137 (13) | 0.61103 (11) | 0.5917 (3) | 0.0336 (6) | |
H9A | −0.0544 | 0.6410 | 0.6285 | 0.040* | |
C10 | −0.04878 (16) | 0.57169 (12) | 0.4865 (4) | 0.0445 (7) | |
H10A | −0.0996 | 0.5754 | 0.4491 | 0.053* | |
C11 | −0.00172 (17) | 0.52668 (12) | 0.4354 (3) | 0.0452 (7) | |
H11A | −0.0203 | 0.4991 | 0.3636 | 0.054* | |
C12 | 0.07225 (16) | 0.52230 (11) | 0.4897 (3) | 0.0383 (6) | |
H12A | 0.1045 | 0.4913 | 0.4558 | 0.046* | |
C13 | 0.09978 (13) | 0.56291 (10) | 0.5936 (3) | 0.0299 (5) | |
H13A | 0.1510 | 0.5598 | 0.6295 | 0.036* | |
C14 | 0.18656 (12) | 0.83229 (9) | 0.8579 (2) | 0.0216 (5) | |
C15 | 0.23128 (12) | 0.86432 (9) | 0.7569 (3) | 0.0258 (5) | |
H15A | 0.2576 | 0.8447 | 0.6776 | 0.031* | |
C16 | 0.23724 (13) | 0.92527 (10) | 0.7726 (3) | 0.0288 (5) | |
H16A | 0.2676 | 0.9469 | 0.7028 | 0.035* | |
C17 | 0.19980 (12) | 0.95509 (10) | 0.8878 (3) | 0.0261 (5) | |
C18 | 0.15560 (13) | 0.92253 (10) | 0.9869 (3) | 0.0272 (5) | |
H18A | 0.1298 | 0.9421 | 1.0669 | 0.033* | |
C19 | 0.14812 (12) | 0.86219 (9) | 0.9722 (3) | 0.0233 (5) | |
H19A | 0.1165 | 0.8410 | 1.0406 | 0.028* | |
C20 | 0.20544 (15) | 1.02143 (10) | 0.9034 (3) | 0.0369 (6) | |
H20A | 0.2565 | 1.0345 | 0.8717 | 0.055* | |
H20B | 0.1969 | 1.0326 | 1.0089 | 0.055* | |
H20C | 0.1665 | 1.0401 | 0.8396 | 0.055* | |
P2 | 0.04486 (3) | 0.71518 (2) | 0.21889 (7) | 0.01941 (12) | |
O2 | 0.06608 (8) | 0.73328 (7) | 0.06447 (16) | 0.0245 (3) | |
N3 | 0.09188 (10) | 0.65682 (8) | 0.2761 (2) | 0.0238 (4) | |
H3N | 0.0676 (12) | 0.6382 (10) | 0.348 (2) | 0.029* | |
N4 | 0.06232 (10) | 0.76608 (8) | 0.3473 (2) | 0.0228 (4) | |
H4N | 0.0926 (11) | 0.7567 (11) | 0.4229 (19) | 0.027* | |
C21 | −0.05454 (11) | 0.69441 (9) | 0.2327 (3) | 0.0220 (4) | |
C22 | −0.08405 (13) | 0.65408 (10) | 0.1285 (3) | 0.0270 (5) | |
H22A | −0.0516 | 0.6381 | 0.0526 | 0.032* | |
C23 | −0.16043 (13) | 0.63729 (11) | 0.1354 (3) | 0.0319 (5) | |
H23A | −0.1802 | 0.6095 | 0.0655 | 0.038* | |
C24 | −0.20782 (12) | 0.66129 (10) | 0.2449 (3) | 0.0311 (5) | |
H24A | −0.2602 | 0.6500 | 0.2495 | 0.037* | |
C25 | −0.17947 (13) | 0.70143 (11) | 0.3471 (3) | 0.0298 (5) | |
H25A | −0.2124 | 0.7179 | 0.4214 | 0.036* | |
C26 | −0.10295 (12) | 0.71777 (10) | 0.3418 (3) | 0.0251 (5) | |
H26A | −0.0835 | 0.7451 | 0.4132 | 0.030* | |
C27 | 0.17596 (12) | 0.65569 (10) | 0.2688 (3) | 0.0285 (5) | |
H27A | 0.1959 | 0.6398 | 0.3652 | 0.034* | |
H27B | 0.1948 | 0.6966 | 0.2592 | 0.034* | |
C28 | 0.20848 (12) | 0.61993 (10) | 0.1415 (3) | 0.0260 (5) | |
C29 | 0.28105 (12) | 0.63336 (10) | 0.0882 (3) | 0.0273 (5) | |
H29A | 0.3078 | 0.6662 | 0.1289 | 0.033* | |
C30 | 0.31560 (13) | 0.59950 (11) | −0.0245 (3) | 0.0314 (5) | |
H30A | 0.3654 | 0.6094 | −0.0601 | 0.038* | |
C31 | 0.27733 (14) | 0.55181 (11) | −0.0838 (3) | 0.0333 (6) | |
H31A | 0.3007 | 0.5282 | −0.1595 | 0.040* | |
C32 | 0.20375 (14) | 0.53850 (11) | −0.0314 (3) | 0.0336 (6) | |
H32A | 0.1768 | 0.5059 | −0.0728 | 0.040* | |
C33 | 0.16999 (14) | 0.57194 (10) | 0.0791 (3) | 0.0295 (5) | |
H33A | 0.1199 | 0.5623 | 0.1135 | 0.035* | |
C34 | 0.04819 (11) | 0.82734 (9) | 0.3348 (2) | 0.0213 (4) | |
C35 | −0.00629 (11) | 0.85024 (9) | 0.2371 (3) | 0.0237 (5) | |
H35A | −0.0353 | 0.8247 | 0.1743 | 0.028* | |
C36 | −0.01838 (11) | 0.91083 (9) | 0.2310 (3) | 0.0246 (5) | |
H36A | −0.0558 | 0.9260 | 0.1634 | 0.029* | |
C37 | 0.02266 (12) | 0.94973 (9) | 0.3209 (3) | 0.0246 (5) | |
C38 | 0.07609 (12) | 0.92604 (10) | 0.4203 (3) | 0.0253 (5) | |
H38A | 0.1042 | 0.9517 | 0.4845 | 0.030* | |
C39 | 0.08933 (12) | 0.86593 (10) | 0.4279 (2) | 0.0226 (5) | |
H39A | 0.1264 | 0.8509 | 0.4964 | 0.027* | |
C40 | 0.01109 (14) | 1.01544 (10) | 0.3069 (3) | 0.0336 (6) | |
H40A | −0.0393 | 1.0233 | 0.2622 | 0.050* | |
H40B | 0.0512 | 1.0321 | 0.2423 | 0.050* | |
H40C | 0.0138 | 1.0335 | 0.4072 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0210 (2) | 0.0161 (3) | 0.0216 (3) | −0.00005 (19) | −0.0007 (2) | −0.0001 (3) |
O1 | 0.0279 (8) | 0.0257 (9) | 0.0255 (8) | 0.0023 (7) | −0.0016 (7) | 0.0031 (7) |
N1 | 0.0225 (9) | 0.0186 (9) | 0.0272 (10) | −0.0020 (7) | −0.0041 (8) | 0.0012 (8) |
N2 | 0.0259 (9) | 0.0191 (10) | 0.0228 (10) | −0.0015 (7) | 0.0042 (8) | 0.0009 (8) |
C1 | 0.0217 (9) | 0.0176 (10) | 0.0226 (10) | −0.0019 (8) | 0.0010 (10) | 0.0028 (10) |
C2 | 0.0256 (10) | 0.0214 (12) | 0.0219 (11) | −0.0016 (9) | −0.0020 (9) | 0.0015 (9) |
C3 | 0.0283 (12) | 0.0215 (12) | 0.0276 (12) | 0.0026 (9) | 0.0034 (10) | 0.0047 (10) |
C4 | 0.0224 (9) | 0.0276 (12) | 0.0341 (12) | 0.0019 (9) | −0.0004 (10) | 0.0072 (12) |
C5 | 0.0248 (11) | 0.0279 (13) | 0.0293 (12) | −0.0054 (9) | −0.0073 (10) | 0.0036 (10) |
C6 | 0.0285 (11) | 0.0196 (11) | 0.0235 (11) | −0.0010 (9) | −0.0016 (10) | −0.0009 (9) |
C7 | 0.0254 (11) | 0.0283 (13) | 0.0329 (13) | −0.0039 (9) | 0.0005 (10) | −0.0036 (10) |
C8 | 0.0298 (12) | 0.0200 (13) | 0.0268 (11) | −0.0078 (9) | 0.0012 (10) | 0.0049 (9) |
C9 | 0.0299 (12) | 0.0274 (13) | 0.0437 (15) | −0.0074 (10) | −0.0046 (12) | 0.0052 (12) |
C10 | 0.0379 (14) | 0.0381 (17) | 0.0576 (18) | −0.0134 (12) | −0.0161 (14) | 0.0065 (14) |
C11 | 0.0618 (18) | 0.0311 (15) | 0.0428 (15) | −0.0177 (13) | −0.0105 (14) | −0.0020 (12) |
C12 | 0.0515 (16) | 0.0245 (14) | 0.0389 (14) | −0.0057 (11) | 0.0000 (13) | −0.0002 (12) |
C13 | 0.0330 (12) | 0.0252 (12) | 0.0316 (12) | −0.0041 (10) | −0.0010 (11) | 0.0030 (11) |
C14 | 0.0246 (10) | 0.0150 (11) | 0.0251 (11) | 0.0005 (8) | −0.0032 (9) | 0.0012 (9) |
C15 | 0.0301 (11) | 0.0204 (11) | 0.0271 (12) | −0.0015 (9) | 0.0039 (10) | 0.0007 (9) |
C16 | 0.0332 (12) | 0.0228 (12) | 0.0303 (12) | −0.0034 (9) | 0.0026 (10) | 0.0062 (10) |
C17 | 0.0267 (11) | 0.0180 (11) | 0.0335 (12) | 0.0002 (9) | −0.0044 (10) | 0.0025 (10) |
C18 | 0.0293 (12) | 0.0210 (12) | 0.0311 (12) | 0.0028 (9) | 0.0031 (10) | −0.0034 (10) |
C19 | 0.0246 (11) | 0.0182 (11) | 0.0270 (11) | −0.0001 (8) | 0.0022 (9) | 0.0023 (9) |
C20 | 0.0451 (14) | 0.0174 (13) | 0.0482 (16) | 0.0001 (11) | 0.0015 (13) | 0.0006 (11) |
P2 | 0.0204 (2) | 0.0162 (2) | 0.0216 (2) | −0.00022 (19) | −0.0005 (2) | 0.0002 (3) |
O2 | 0.0253 (7) | 0.0233 (9) | 0.0248 (8) | −0.0011 (6) | −0.0005 (7) | 0.0019 (7) |
N3 | 0.0236 (9) | 0.0191 (10) | 0.0287 (10) | 0.0017 (7) | 0.0035 (8) | 0.0037 (8) |
N4 | 0.0253 (9) | 0.0203 (10) | 0.0227 (10) | 0.0014 (8) | −0.0044 (8) | −0.0005 (8) |
C21 | 0.0246 (10) | 0.0183 (10) | 0.0230 (11) | −0.0002 (8) | −0.0029 (10) | 0.0032 (10) |
C22 | 0.0283 (12) | 0.0251 (13) | 0.0276 (12) | −0.0003 (9) | 0.0003 (10) | −0.0028 (10) |
C23 | 0.0300 (12) | 0.0325 (14) | 0.0332 (13) | −0.0084 (10) | −0.0019 (11) | −0.0066 (11) |
C24 | 0.0229 (10) | 0.0356 (13) | 0.0349 (14) | −0.0046 (9) | 0.0018 (10) | 0.0015 (11) |
C25 | 0.0280 (12) | 0.0323 (13) | 0.0292 (12) | 0.0024 (10) | 0.0043 (11) | −0.0004 (10) |
C26 | 0.0288 (11) | 0.0225 (12) | 0.0238 (11) | −0.0008 (9) | 0.0026 (10) | −0.0005 (9) |
C27 | 0.0271 (11) | 0.0253 (12) | 0.0330 (12) | 0.0038 (9) | −0.0051 (10) | 0.0003 (10) |
C28 | 0.0269 (11) | 0.0210 (12) | 0.0300 (12) | 0.0046 (9) | −0.0048 (10) | 0.0069 (10) |
C29 | 0.0279 (11) | 0.0213 (12) | 0.0327 (12) | −0.0008 (9) | −0.0032 (10) | 0.0040 (10) |
C30 | 0.0264 (11) | 0.0324 (14) | 0.0354 (13) | 0.0053 (10) | 0.0014 (11) | 0.0098 (11) |
C31 | 0.0423 (14) | 0.0266 (13) | 0.0311 (13) | 0.0112 (11) | 0.0007 (11) | 0.0013 (11) |
C32 | 0.0394 (14) | 0.0214 (13) | 0.0401 (15) | 0.0003 (10) | −0.0018 (12) | 0.0020 (11) |
C33 | 0.0319 (12) | 0.0233 (12) | 0.0334 (13) | −0.0025 (9) | −0.0053 (11) | 0.0054 (11) |
C34 | 0.0224 (10) | 0.0173 (11) | 0.0243 (11) | 0.0012 (8) | 0.0036 (9) | 0.0012 (9) |
C35 | 0.0238 (10) | 0.0211 (11) | 0.0262 (12) | −0.0006 (8) | −0.0008 (10) | −0.0031 (10) |
C36 | 0.0240 (10) | 0.0236 (11) | 0.0261 (12) | 0.0035 (8) | −0.0015 (10) | 0.0039 (10) |
C37 | 0.0254 (11) | 0.0209 (11) | 0.0274 (11) | 0.0003 (9) | 0.0051 (10) | 0.0013 (10) |
C38 | 0.0258 (11) | 0.0212 (12) | 0.0289 (11) | −0.0031 (9) | 0.0025 (10) | −0.0023 (10) |
C39 | 0.0228 (11) | 0.0227 (12) | 0.0223 (10) | 0.0010 (9) | −0.0016 (9) | 0.0009 (9) |
C40 | 0.0381 (13) | 0.0203 (12) | 0.0425 (14) | 0.0022 (10) | −0.0036 (12) | −0.0027 (11) |
P1—O1 | 1.4746 (16) | P2—O2 | 1.4757 (15) |
P1—N1 | 1.6422 (18) | P2—N3 | 1.6391 (19) |
P1—N2 | 1.6489 (19) | P2—N4 | 1.6502 (19) |
P1—C1 | 1.7978 (19) | P2—C21 | 1.800 (2) |
N1—C7 | 1.465 (3) | N3—C27 | 1.468 (3) |
N1—H1N | 0.878 (10) | N3—H3N | 0.874 (10) |
N2—C14 | 1.412 (3) | N4—C34 | 1.417 (3) |
N2—H2N | 0.868 (10) | N4—H4N | 0.879 (10) |
C1—C6 | 1.394 (3) | C21—C26 | 1.389 (3) |
C1—C2 | 1.402 (3) | C21—C22 | 1.399 (3) |
C2—C3 | 1.379 (3) | C22—C23 | 1.387 (3) |
C2—H2B | 0.9500 | C22—H22A | 0.9500 |
C3—C4 | 1.384 (3) | C23—C24 | 1.386 (3) |
C3—H3A | 0.9500 | C23—H23A | 0.9500 |
C4—C5 | 1.386 (3) | C24—C25 | 1.377 (3) |
C4—H4A | 0.9500 | C24—H24A | 0.9500 |
C5—C6 | 1.384 (3) | C25—C26 | 1.386 (3) |
C5—H5A | 0.9500 | C25—H25A | 0.9500 |
C6—H6A | 0.9500 | C26—H26A | 0.9500 |
C7—C8 | 1.509 (3) | C27—C28 | 1.501 (3) |
C7—H7A | 0.9900 | C27—H27A | 0.9900 |
C7—H7B | 0.9900 | C27—H27B | 0.9900 |
C8—C9 | 1.383 (3) | C28—C29 | 1.385 (3) |
C8—C13 | 1.387 (3) | C28—C33 | 1.394 (3) |
C9—C10 | 1.377 (4) | C29—C30 | 1.397 (3) |
C9—H9A | 0.9500 | C29—H29A | 0.9500 |
C10—C11 | 1.387 (4) | C30—C31 | 1.376 (4) |
C10—H10A | 0.9500 | C30—H30A | 0.9500 |
C11—C12 | 1.380 (4) | C31—C32 | 1.397 (3) |
C11—H11A | 0.9500 | C31—H31A | 0.9500 |
C12—C13 | 1.389 (3) | C32—C33 | 1.372 (3) |
C12—H12A | 0.9500 | C32—H32A | 0.9500 |
C13—H13A | 0.9500 | C33—H33A | 0.9500 |
C14—C19 | 1.391 (3) | C34—C35 | 1.387 (3) |
C14—C15 | 1.392 (3) | C34—C39 | 1.401 (3) |
C15—C16 | 1.395 (3) | C35—C36 | 1.393 (3) |
C15—H15A | 0.9500 | C35—H35A | 0.9500 |
C16—C17 | 1.388 (3) | C36—C37 | 1.388 (3) |
C16—H16A | 0.9500 | C36—H36A | 0.9500 |
C17—C18 | 1.383 (3) | C37—C38 | 1.390 (3) |
C17—C20 | 1.516 (3) | C37—C40 | 1.511 (3) |
C18—C19 | 1.383 (3) | C38—C39 | 1.386 (3) |
C18—H18A | 0.9500 | C38—H38A | 0.9500 |
C19—H19A | 0.9500 | C39—H39A | 0.9500 |
C20—H20A | 0.9800 | C40—H40A | 0.9800 |
C20—H20B | 0.9800 | C40—H40B | 0.9800 |
C20—H20C | 0.9800 | C40—H40C | 0.9800 |
O1—P1—N1 | 113.30 (10) | O2—P2—N3 | 112.76 (10) |
O1—P1—N2 | 113.11 (10) | O2—P2—N4 | 113.43 (10) |
N1—P1—N2 | 105.57 (9) | N3—P2—N4 | 105.12 (10) |
O1—P1—C1 | 112.06 (10) | O2—P2—C21 | 112.16 (10) |
N1—P1—C1 | 103.50 (9) | N3—P2—C21 | 104.40 (9) |
N2—P1—C1 | 108.66 (10) | N4—P2—C21 | 108.33 (10) |
C7—N1—P1 | 120.93 (15) | C27—N3—P2 | 120.01 (15) |
C7—N1—H1N | 117.6 (16) | C27—N3—H3N | 120.4 (16) |
P1—N1—H1N | 111.1 (16) | P2—N3—H3N | 112.1 (16) |
C14—N2—P1 | 128.68 (16) | C34—N4—P2 | 127.02 (16) |
C14—N2—H2N | 112.9 (17) | C34—N4—H4N | 113.6 (17) |
P1—N2—H2N | 116.8 (17) | P2—N4—H4N | 117.8 (17) |
C6—C1—C2 | 119.09 (18) | C26—C21—C22 | 119.09 (19) |
C6—C1—P1 | 122.57 (17) | C26—C21—P2 | 122.16 (16) |
C2—C1—P1 | 118.33 (16) | C22—C21—P2 | 118.75 (16) |
C3—C2—C1 | 120.7 (2) | C23—C22—C21 | 120.3 (2) |
C3—C2—H2B | 119.7 | C23—C22—H22A | 119.9 |
C1—C2—H2B | 119.7 | C21—C22—H22A | 119.9 |
C2—C3—C4 | 119.6 (2) | C24—C23—C22 | 119.7 (2) |
C2—C3—H3A | 120.2 | C24—C23—H23A | 120.1 |
C4—C3—H3A | 120.2 | C22—C23—H23A | 120.1 |
C3—C4—C5 | 120.47 (19) | C25—C24—C23 | 120.4 (2) |
C3—C4—H4A | 119.8 | C25—C24—H24A | 119.8 |
C5—C4—H4A | 119.8 | C23—C24—H24A | 119.8 |
C6—C5—C4 | 120.2 (2) | C24—C25—C26 | 120.0 (2) |
C6—C5—H5A | 119.9 | C24—C25—H25A | 120.0 |
C4—C5—H5A | 119.9 | C26—C25—H25A | 120.0 |
C5—C6—C1 | 120.0 (2) | C25—C26—C21 | 120.4 (2) |
C5—C6—H6A | 120.0 | C25—C26—H26A | 119.8 |
C1—C6—H6A | 120.0 | C21—C26—H26A | 119.8 |
N1—C7—C8 | 113.75 (18) | N3—C27—C28 | 114.82 (19) |
N1—C7—H7A | 108.8 | N3—C27—H27A | 108.6 |
C8—C7—H7A | 108.8 | C28—C27—H27A | 108.6 |
N1—C7—H7B | 108.8 | N3—C27—H27B | 108.6 |
C8—C7—H7B | 108.8 | C28—C27—H27B | 108.6 |
H7A—C7—H7B | 107.7 | H27A—C27—H27B | 107.5 |
C9—C8—C13 | 118.4 (2) | C29—C28—C33 | 118.5 (2) |
C9—C8—C7 | 119.0 (2) | C29—C28—C27 | 118.8 (2) |
C13—C8—C7 | 122.6 (2) | C33—C28—C27 | 122.6 (2) |
C10—C9—C8 | 121.7 (3) | C28—C29—C30 | 121.1 (2) |
C10—C9—H9A | 119.1 | C28—C29—H29A | 119.4 |
C8—C9—H9A | 119.1 | C30—C29—H29A | 119.4 |
C9—C10—C11 | 119.6 (3) | C31—C30—C29 | 119.8 (2) |
C9—C10—H10A | 120.2 | C31—C30—H30A | 120.1 |
C11—C10—H10A | 120.2 | C29—C30—H30A | 120.1 |
C12—C11—C10 | 119.5 (3) | C30—C31—C32 | 119.3 (2) |
C12—C11—H11A | 120.3 | C30—C31—H31A | 120.4 |
C10—C11—H11A | 120.3 | C32—C31—H31A | 120.4 |
C11—C12—C13 | 120.4 (3) | C33—C32—C31 | 120.7 (2) |
C11—C12—H12A | 119.8 | C33—C32—H32A | 119.6 |
C13—C12—H12A | 119.8 | C31—C32—H32A | 119.6 |
C8—C13—C12 | 120.4 (2) | C32—C33—C28 | 120.6 (2) |
C8—C13—H13A | 119.8 | C32—C33—H33A | 119.7 |
C12—C13—H13A | 119.8 | C28—C33—H33A | 119.7 |
C19—C14—C15 | 118.9 (2) | C35—C34—C39 | 118.92 (19) |
C19—C14—N2 | 117.9 (2) | C35—C34—N4 | 122.40 (19) |
C15—C14—N2 | 123.3 (2) | C39—C34—N4 | 118.65 (19) |
C14—C15—C16 | 119.8 (2) | C34—C35—C36 | 119.9 (2) |
C14—C15—H15A | 120.1 | C34—C35—H35A | 120.1 |
C16—C15—H15A | 120.1 | C36—C35—H35A | 120.1 |
C17—C16—C15 | 121.5 (2) | C37—C36—C35 | 121.9 (2) |
C17—C16—H16A | 119.3 | C37—C36—H36A | 119.0 |
C15—C16—H16A | 119.3 | C35—C36—H36A | 119.0 |
C18—C17—C16 | 117.9 (2) | C36—C37—C38 | 117.5 (2) |
C18—C17—C20 | 120.6 (2) | C36—C37—C40 | 120.9 (2) |
C16—C17—C20 | 121.4 (2) | C38—C37—C40 | 121.6 (2) |
C17—C18—C19 | 121.5 (2) | C39—C38—C37 | 121.6 (2) |
C17—C18—H18A | 119.2 | C39—C38—H38A | 119.2 |
C19—C18—H18A | 119.2 | C37—C38—H38A | 119.2 |
C18—C19—C14 | 120.5 (2) | C38—C39—C34 | 120.1 (2) |
C18—C19—H19A | 119.8 | C38—C39—H39A | 119.9 |
C14—C19—H19A | 119.8 | C34—C39—H39A | 119.9 |
C17—C20—H20A | 109.5 | C37—C40—H40A | 109.5 |
C17—C20—H20B | 109.5 | C37—C40—H40B | 109.5 |
H20A—C20—H20B | 109.5 | H40A—C40—H40B | 109.5 |
C17—C20—H20C | 109.5 | C37—C40—H40C | 109.5 |
H20A—C20—H20C | 109.5 | H40A—C40—H40C | 109.5 |
H20B—C20—H20C | 109.5 | H40B—C40—H40C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2i | 0.87 (1) | 2.00 (1) | 2.852 (2) | 169 (2) |
N4—H4N···O1 | 0.88 (1) | 1.96 (1) | 2.818 (2) | 167 (2) |
Symmetry code: (i) x, y, z+1. |
C16H20NOP | Dx = 1.205 Mg m−3 |
Mr = 273.30 | Melting point: 381 K |
Tetragonal, P421c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -4 2n | Cell parameters from 9050 reflections |
a = 18.7952 (3) Å | θ = 1.5–29.7° |
c = 8.5279 (3) Å | µ = 0.18 mm−1 |
V = 3012.56 (13) Å3 | T = 120 K |
Z = 8 | Block, colourless |
F(000) = 1168 | 0.25 × 0.20 × 0.20 mm |
Rigaku Saturn724+ (2x2 bin mode) diffractometer | 2762 independent reflections |
Radiation source: Rotating Anode | 2550 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.064 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 25.3°, θmin = 3.1° |
profile data from ω–scans | h = −20→22 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −22→22 |
Tmin = 0.008, Tmax = 1.000 | l = −10→9 |
15254 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)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0737P)2 + 2.3114P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2762 reflections | Δρmax = 0.55 e Å−3 |
177 parameters | Δρmin = −0.34 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1192 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.37 (17) |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.67735 (4) | 0.27034 (4) | −0.00139 (10) | 0.0257 (2) | |
O1 | 0.71589 (13) | 0.21220 (12) | 0.0818 (3) | 0.0339 (5) | |
N1 | 0.62736 (15) | 0.25104 (15) | −0.1523 (3) | 0.0294 (6) | |
H1N | 0.6507 (16) | 0.249 (2) | −0.241 (2) | 0.035* | |
C1 | 0.73865 (16) | 0.33488 (16) | −0.0780 (4) | 0.0272 (7) | |
C2 | 0.80764 (17) | 0.33419 (18) | −0.0194 (4) | 0.0374 (8) | |
H2 | 0.8214 | 0.2988 | 0.0543 | 0.045* | |
C3 | 0.8563 (2) | 0.3846 (2) | −0.0677 (5) | 0.0450 (9) | |
H3 | 0.9034 | 0.3840 | −0.0273 | 0.054* | |
C4 | 0.8364 (2) | 0.43563 (19) | −0.1747 (5) | 0.0425 (9) | |
H4 | 0.8699 | 0.4703 | −0.2080 | 0.051* | |
C5 | 0.76852 (19) | 0.43680 (17) | −0.2335 (4) | 0.0370 (8) | |
H5 | 0.7552 | 0.4724 | −0.3069 | 0.044* | |
C6 | 0.71975 (18) | 0.38665 (16) | −0.1867 (4) | 0.0309 (7) | |
H6 | 0.6729 | 0.3874 | −0.2287 | 0.037* | |
C7 | 0.62012 (16) | 0.31622 (16) | 0.1345 (4) | 0.0266 (7) | |
C8 | 0.63071 (17) | 0.30557 (18) | 0.2952 (4) | 0.0326 (7) | |
H8 | 0.6658 | 0.2729 | 0.3302 | 0.039* | |
C9 | 0.59024 (18) | 0.3425 (2) | 0.4028 (4) | 0.0390 (9) | |
H9 | 0.5977 | 0.3349 | 0.5117 | 0.047* | |
C10 | 0.53954 (19) | 0.3899 (2) | 0.3550 (5) | 0.0413 (9) | |
H10 | 0.5123 | 0.4151 | 0.4305 | 0.050* | |
C11 | 0.52773 (18) | 0.40119 (18) | 0.1941 (5) | 0.0378 (9) | |
H11 | 0.4924 | 0.4338 | 0.1599 | 0.045* | |
C12 | 0.56827 (18) | 0.36420 (17) | 0.0866 (4) | 0.0316 (7) | |
H12 | 0.5606 | 0.3717 | −0.0223 | 0.038* | |
C13 | 0.5687 (2) | 0.2003 (2) | −0.1361 (4) | 0.0426 (9) | |
H13 | 0.5448 | 0.2090 | −0.0331 | 0.051* | |
C14 | 0.5959 (2) | 0.1212 (2) | −0.1387 (5) | 0.0525 (11) | |
H14A | 0.6153 | 0.1103 | −0.2426 | 0.079* | |
H14B | 0.5563 | 0.0890 | −0.1157 | 0.079* | |
H14C | 0.6332 | 0.1152 | −0.0595 | 0.079* | |
C15 | 0.5155 (2) | 0.2120 (3) | −0.2631 (6) | 0.0559 (11) | |
H15A | 0.5399 | 0.2072 | −0.3654 | 0.067* | |
H15B | 0.4792 | 0.1741 | −0.2568 | 0.067* | |
C16 | 0.4807 (2) | 0.2787 (3) | −0.2590 (6) | 0.0681 (13) | |
H16A | 0.4563 | 0.2843 | −0.1583 | 0.102* | |
H16B | 0.4459 | 0.2811 | −0.3444 | 0.102* | |
H16C | 0.5158 | 0.3168 | −0.2717 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0312 (4) | 0.0257 (4) | 0.0203 (4) | 0.0035 (3) | 0.0007 (4) | 0.0007 (4) |
O1 | 0.0430 (13) | 0.0319 (12) | 0.0268 (12) | 0.0103 (10) | 0.0011 (11) | 0.0022 (10) |
N1 | 0.0346 (15) | 0.0327 (14) | 0.0209 (13) | −0.0056 (12) | 0.0039 (12) | −0.0014 (11) |
C1 | 0.0280 (15) | 0.0277 (16) | 0.0258 (15) | 0.0014 (13) | 0.0042 (13) | −0.0057 (13) |
C2 | 0.0318 (16) | 0.0403 (18) | 0.0401 (19) | 0.0073 (14) | −0.0048 (15) | −0.0003 (16) |
C3 | 0.0312 (18) | 0.049 (2) | 0.055 (2) | −0.0010 (17) | −0.0005 (17) | −0.0075 (19) |
C4 | 0.040 (2) | 0.0347 (18) | 0.052 (2) | −0.0065 (16) | 0.0083 (18) | −0.0070 (17) |
C5 | 0.043 (2) | 0.0233 (15) | 0.045 (2) | 0.0058 (15) | 0.0054 (17) | 0.0000 (15) |
C6 | 0.0340 (17) | 0.0272 (16) | 0.0316 (17) | 0.0034 (13) | 0.0010 (15) | −0.0010 (14) |
C7 | 0.0279 (15) | 0.0246 (15) | 0.0273 (16) | −0.0023 (13) | 0.0010 (13) | −0.0021 (13) |
C8 | 0.0292 (16) | 0.0422 (19) | 0.0264 (16) | 0.0032 (15) | 0.0011 (14) | −0.0045 (14) |
C9 | 0.0378 (18) | 0.050 (2) | 0.0289 (18) | −0.0042 (17) | 0.0016 (15) | −0.0130 (16) |
C10 | 0.0329 (18) | 0.044 (2) | 0.047 (2) | −0.0021 (16) | 0.0078 (16) | −0.0220 (18) |
C11 | 0.0259 (16) | 0.0318 (17) | 0.056 (2) | −0.0006 (14) | 0.0014 (17) | −0.0078 (17) |
C12 | 0.0340 (17) | 0.0288 (16) | 0.0321 (17) | −0.0022 (14) | 0.0007 (15) | −0.0022 (14) |
C13 | 0.046 (2) | 0.051 (2) | 0.0307 (18) | −0.0153 (18) | 0.0085 (17) | −0.0068 (16) |
C14 | 0.058 (2) | 0.050 (2) | 0.049 (2) | −0.003 (2) | −0.001 (2) | −0.014 (2) |
C15 | 0.041 (2) | 0.068 (3) | 0.059 (3) | −0.009 (2) | −0.0042 (19) | 0.000 (2) |
C16 | 0.053 (3) | 0.091 (4) | 0.060 (3) | 0.002 (3) | 0.000 (2) | −0.010 (3) |
P1—O1 | 1.491 (2) | C8—H8 | 0.9500 |
P1—N1 | 1.634 (3) | C9—C10 | 1.366 (5) |
P1—C1 | 1.796 (3) | C9—H9 | 0.9500 |
P1—C7 | 1.801 (3) | C10—C11 | 1.407 (6) |
N1—C13 | 1.465 (4) | C10—H10 | 0.9500 |
N1—H1N | 0.874 (10) | C11—C12 | 1.380 (5) |
C1—C2 | 1.390 (4) | C11—H11 | 0.9500 |
C1—C6 | 1.390 (4) | C12—H12 | 0.9500 |
C2—C3 | 1.380 (5) | C13—C15 | 1.489 (6) |
C2—H2 | 0.9500 | C13—C14 | 1.572 (6) |
C3—C4 | 1.375 (5) | C13—H13 | 1.0000 |
C3—H3 | 0.9500 | C14—H14A | 0.9800 |
C4—C5 | 1.371 (5) | C14—H14B | 0.9800 |
C4—H4 | 0.9500 | C14—H14C | 0.9800 |
C5—C6 | 1.374 (5) | C15—C16 | 1.414 (7) |
C5—H5 | 0.9500 | C15—H15A | 0.9900 |
C6—H6 | 0.9500 | C15—H15B | 0.9900 |
C7—C12 | 1.389 (5) | C16—H16A | 0.9800 |
C7—C8 | 1.399 (4) | C16—H16B | 0.9800 |
C8—C9 | 1.380 (5) | C16—H16C | 0.9800 |
O1—P1—N1 | 119.42 (14) | C8—C9—H9 | 119.5 |
O1—P1—C1 | 110.88 (14) | C9—C10—C11 | 120.0 (3) |
N1—P1—C1 | 103.43 (14) | C9—C10—H10 | 120.0 |
O1—P1—C7 | 109.58 (14) | C11—C10—H10 | 120.0 |
N1—P1—C7 | 105.65 (14) | C12—C11—C10 | 119.0 (3) |
C1—P1—C7 | 107.09 (14) | C12—C11—H11 | 120.5 |
C13—N1—P1 | 120.2 (2) | C10—C11—H11 | 120.5 |
C13—N1—H1N | 116 (2) | C11—C12—C7 | 121.3 (3) |
P1—N1—H1N | 114 (2) | C11—C12—H12 | 119.4 |
C2—C1—C6 | 119.0 (3) | C7—C12—H12 | 119.4 |
C2—C1—P1 | 117.5 (3) | N1—C13—C15 | 109.9 (3) |
C6—C1—P1 | 123.5 (3) | N1—C13—C14 | 111.6 (3) |
C3—C2—C1 | 120.3 (3) | C15—C13—C14 | 110.4 (3) |
C3—C2—H2 | 119.8 | N1—C13—H13 | 108.3 |
C1—C2—H2 | 119.8 | C15—C13—H13 | 108.3 |
C4—C3—C2 | 119.8 (3) | C14—C13—H13 | 108.3 |
C4—C3—H3 | 120.1 | C13—C14—H14A | 109.5 |
C2—C3—H3 | 120.1 | C13—C14—H14B | 109.5 |
C5—C4—C3 | 120.5 (3) | H14A—C14—H14B | 109.5 |
C5—C4—H4 | 119.8 | C13—C14—H14C | 109.5 |
C3—C4—H4 | 119.8 | H14A—C14—H14C | 109.5 |
C4—C5—C6 | 120.2 (3) | H14B—C14—H14C | 109.5 |
C4—C5—H5 | 119.9 | C16—C15—C13 | 115.1 (4) |
C6—C5—H5 | 119.9 | C16—C15—H15A | 108.5 |
C5—C6—C1 | 120.2 (3) | C13—C15—H15A | 108.5 |
C5—C6—H6 | 119.9 | C16—C15—H15B | 108.5 |
C1—C6—H6 | 119.9 | C13—C15—H15B | 108.5 |
C12—C7—C8 | 118.7 (3) | H15A—C15—H15B | 107.5 |
C12—C7—P1 | 122.7 (3) | C15—C16—H16A | 109.5 |
C8—C7—P1 | 118.5 (2) | C15—C16—H16B | 109.5 |
C9—C8—C7 | 120.1 (3) | H16A—C16—H16B | 109.5 |
C9—C8—H8 | 120.0 | C15—C16—H16C | 109.5 |
C7—C8—H8 | 120.0 | H16A—C16—H16C | 109.5 |
C10—C9—C8 | 120.9 (3) | H16B—C16—H16C | 109.5 |
C10—C9—H9 | 119.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.87 (1) | 2.01 (2) | 2.850 (3) | 162 (3) |
Symmetry code: (i) y+1/2, x−1/2, z−1/2. |
C8H12N+·C14H15NO2P− | Dx = 1.238 Mg m−3 |
Mr = 382.43 | Melting point: 436 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7210 reflections |
a = 5.3629 (1) Å | θ = 2.1–29.5° |
b = 13.7260 (3) Å | µ = 0.15 mm−1 |
c = 27.8653 (6) Å | T = 120 K |
V = 2051.20 (7) Å3 | Needle, colourless |
Z = 4 | 0.20 × 0.10 × 0.05 mm |
F(000) = 816 |
Rigaku Saturn724+ (2x2 bin mode) diffractometer | 3764 independent reflections |
Radiation source: Rotating Anode | 3557 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.031 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 25.4°, θmin = 2.9° |
profile data from ω–scans | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −16→16 |
Tmin = 0.752, Tmax = 1.000 | l = −33→33 |
11806 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)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.4266P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3764 reflections | Δρmax = 0.28 e Å−3 |
249 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1551 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (8) |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.53649 (8) | 0.70582 (3) | 0.102705 (14) | 0.01661 (11) | |
O1 | 0.4176 (2) | 0.70034 (8) | 0.05362 (4) | 0.0203 (3) | |
O2 | 0.7760 (2) | 0.76070 (8) | 0.10844 (4) | 0.0231 (3) | |
N1 | 0.3244 (3) | 0.75517 (11) | 0.13835 (5) | 0.0176 (3) | |
H1N | 0.169 (2) | 0.7447 (14) | 0.1329 (7) | 0.021* | |
N2 | 0.0745 (3) | 0.84111 (9) | 0.03747 (5) | 0.0172 (3) | |
H2A | −0.0506 | 0.8368 | 0.0594 | 0.021* | |
H2B | 0.1809 | 0.7901 | 0.0413 | 0.021* | |
H2C | 0.0089 | 0.8396 | 0.0074 | 0.021* | |
C1 | 0.5869 (3) | 0.58138 (12) | 0.12223 (6) | 0.0216 (4) | |
C2 | 0.4168 (4) | 0.50824 (12) | 0.10923 (6) | 0.0266 (4) | |
H2D | 0.2779 | 0.5240 | 0.0896 | 0.032* | |
C3 | 0.4497 (4) | 0.41288 (13) | 0.12488 (7) | 0.0328 (4) | |
H3A | 0.3332 | 0.3640 | 0.1160 | 0.039* | |
C4 | 0.6523 (4) | 0.38909 (14) | 0.15346 (7) | 0.0320 (5) | |
H4A | 0.6760 | 0.3238 | 0.1639 | 0.038* | |
C5 | 0.8196 (4) | 0.46083 (14) | 0.16670 (7) | 0.0319 (5) | |
H5A | 0.9582 | 0.4447 | 0.1864 | 0.038* | |
C6 | 0.7865 (4) | 0.55663 (13) | 0.15131 (7) | 0.0266 (4) | |
H6A | 0.9020 | 0.6054 | 0.1609 | 0.032* | |
C7 | 0.3941 (4) | 0.89561 (14) | 0.19150 (7) | 0.0349 (5) | |
H7A | 0.5263 | 0.9213 | 0.1708 | 0.052* | |
H7B | 0.4274 | 0.9142 | 0.2248 | 0.052* | |
H7C | 0.2331 | 0.9225 | 0.1814 | 0.052* | |
C8 | 0.3873 (3) | 0.78453 (12) | 0.18750 (6) | 0.0207 (4) | |
H8A | 0.5601 | 0.7606 | 0.1940 | 0.025* | |
C9 | 0.2165 (3) | 0.73636 (12) | 0.22426 (6) | 0.0189 (4) | |
C10 | 0.2671 (4) | 0.64161 (13) | 0.23949 (6) | 0.0256 (4) | |
H10A | 0.4066 | 0.6078 | 0.2267 | 0.031* | |
C11 | 0.1164 (4) | 0.59637 (14) | 0.27301 (7) | 0.0311 (5) | |
H11A | 0.1535 | 0.5319 | 0.2832 | 0.037* | |
C12 | −0.0881 (4) | 0.64447 (14) | 0.29186 (7) | 0.0299 (4) | |
H12A | −0.1909 | 0.6133 | 0.3150 | 0.036* | |
C13 | −0.1419 (4) | 0.73817 (14) | 0.27678 (7) | 0.0279 (4) | |
H13A | −0.2823 | 0.7716 | 0.2895 | 0.034* | |
C14 | 0.0096 (3) | 0.78320 (12) | 0.24312 (6) | 0.0234 (4) | |
H14A | −0.0291 | 0.8474 | 0.2328 | 0.028* | |
C15 | 0.3990 (3) | 0.94562 (13) | 0.00361 (6) | 0.0239 (4) | |
H15A | 0.5082 | 0.8884 | 0.0026 | 0.036* | |
H15B | 0.4997 | 1.0043 | 0.0087 | 0.036* | |
H15C | 0.3087 | 0.9512 | −0.0268 | 0.036* | |
C16 | 0.2133 (3) | 0.93465 (12) | 0.04454 (6) | 0.0188 (4) | |
H16A | 0.3110 | 0.9286 | 0.0750 | 0.023* | |
C17 | 0.0305 (3) | 1.01829 (11) | 0.05097 (6) | 0.0198 (4) | |
C18 | −0.1226 (4) | 1.01897 (14) | 0.09136 (6) | 0.0286 (4) | |
H18A | −0.1114 | 0.9673 | 0.1139 | 0.034* | |
C19 | −0.2905 (4) | 1.09362 (15) | 0.09915 (7) | 0.0358 (5) | |
H19A | −0.3944 | 1.0928 | 0.1267 | 0.043* | |
C20 | −0.3070 (4) | 1.16981 (14) | 0.06657 (8) | 0.0364 (5) | |
H20A | −0.4204 | 1.2218 | 0.0720 | 0.044* | |
C21 | −0.1583 (4) | 1.16967 (14) | 0.02640 (8) | 0.0377 (5) | |
H21A | −0.1708 | 1.2214 | 0.0039 | 0.045* | |
C22 | 0.0107 (4) | 1.09435 (13) | 0.01841 (7) | 0.0294 (4) | |
H22A | 0.1127 | 1.0951 | −0.0094 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0155 (2) | 0.01943 (19) | 0.0150 (2) | 0.00198 (18) | 0.00143 (17) | 0.00226 (15) |
O1 | 0.0222 (6) | 0.0244 (6) | 0.0145 (5) | 0.0052 (6) | 0.0002 (5) | 0.0005 (5) |
O2 | 0.0164 (6) | 0.0275 (6) | 0.0253 (6) | −0.0016 (5) | 0.0018 (5) | 0.0058 (5) |
N1 | 0.0130 (7) | 0.0249 (7) | 0.0148 (7) | −0.0001 (6) | −0.0011 (5) | −0.0020 (6) |
N2 | 0.0163 (7) | 0.0187 (6) | 0.0165 (6) | 0.0020 (6) | −0.0012 (6) | −0.0005 (5) |
C1 | 0.0231 (10) | 0.0260 (9) | 0.0159 (8) | 0.0072 (8) | 0.0024 (7) | 0.0015 (7) |
C2 | 0.0271 (10) | 0.0243 (8) | 0.0283 (9) | 0.0019 (8) | 0.0002 (8) | 0.0011 (8) |
C3 | 0.0337 (11) | 0.0260 (9) | 0.0386 (11) | −0.0027 (9) | 0.0031 (10) | −0.0013 (8) |
C4 | 0.0333 (11) | 0.0266 (9) | 0.0360 (11) | 0.0088 (9) | 0.0069 (9) | 0.0079 (8) |
C5 | 0.0298 (11) | 0.0304 (10) | 0.0355 (11) | 0.0044 (9) | −0.0019 (9) | 0.0090 (8) |
C6 | 0.0233 (10) | 0.0273 (9) | 0.0293 (10) | −0.0011 (8) | −0.0017 (8) | 0.0033 (8) |
C7 | 0.0476 (13) | 0.0284 (9) | 0.0287 (10) | −0.0149 (10) | 0.0104 (10) | −0.0051 (8) |
C8 | 0.0199 (8) | 0.0263 (9) | 0.0159 (8) | −0.0043 (8) | −0.0012 (7) | −0.0010 (7) |
C9 | 0.0189 (9) | 0.0248 (9) | 0.0131 (7) | −0.0046 (7) | −0.0020 (7) | −0.0019 (6) |
C10 | 0.0245 (10) | 0.0280 (9) | 0.0242 (9) | 0.0023 (8) | 0.0018 (8) | −0.0003 (7) |
C11 | 0.0370 (12) | 0.0273 (9) | 0.0289 (10) | 0.0013 (9) | −0.0004 (9) | 0.0077 (8) |
C12 | 0.0292 (11) | 0.0374 (10) | 0.0230 (9) | −0.0087 (9) | 0.0037 (8) | 0.0053 (8) |
C13 | 0.0208 (9) | 0.0373 (10) | 0.0257 (9) | −0.0008 (8) | 0.0052 (8) | −0.0059 (8) |
C14 | 0.0230 (9) | 0.0242 (8) | 0.0228 (8) | 0.0005 (8) | −0.0020 (8) | 0.0000 (7) |
C15 | 0.0179 (9) | 0.0257 (9) | 0.0282 (9) | −0.0034 (8) | 0.0025 (8) | −0.0001 (7) |
C16 | 0.0161 (8) | 0.0218 (8) | 0.0184 (8) | −0.0026 (7) | −0.0038 (7) | −0.0012 (6) |
C17 | 0.0186 (9) | 0.0189 (8) | 0.0220 (8) | −0.0012 (8) | −0.0041 (7) | −0.0027 (6) |
C18 | 0.0332 (11) | 0.0301 (9) | 0.0224 (9) | 0.0080 (9) | −0.0014 (8) | −0.0009 (7) |
C19 | 0.0382 (12) | 0.0411 (11) | 0.0282 (10) | 0.0139 (10) | 0.0013 (10) | −0.0074 (9) |
C20 | 0.0372 (12) | 0.0255 (10) | 0.0464 (12) | 0.0105 (9) | −0.0036 (10) | −0.0083 (9) |
C21 | 0.0358 (12) | 0.0213 (9) | 0.0559 (14) | 0.0029 (9) | 0.0015 (11) | 0.0108 (9) |
C22 | 0.0247 (10) | 0.0251 (9) | 0.0383 (10) | −0.0019 (8) | 0.0045 (9) | 0.0063 (8) |
P1—O2 | 1.4979 (13) | C9—C10 | 1.395 (2) |
P1—O1 | 1.5111 (11) | C10—C11 | 1.382 (3) |
P1—N1 | 1.6551 (14) | C10—H10A | 0.9500 |
P1—C1 | 1.8129 (17) | C11—C12 | 1.383 (3) |
N1—C8 | 1.467 (2) | C11—H11A | 0.9500 |
N1—H1N | 0.861 (9) | C12—C13 | 1.384 (3) |
N2—C16 | 1.497 (2) | C12—H12A | 0.9500 |
N2—H2A | 0.9100 | C13—C14 | 1.386 (3) |
N2—H2B | 0.9100 | C13—H13A | 0.9500 |
N2—H2C | 0.9100 | C14—H14A | 0.9500 |
C1—C6 | 1.385 (3) | C15—C16 | 1.522 (2) |
C1—C2 | 1.404 (3) | C15—H15A | 0.9800 |
C2—C3 | 1.391 (3) | C15—H15B | 0.9800 |
C2—H2D | 0.9500 | C15—H15C | 0.9800 |
C3—C4 | 1.386 (3) | C16—C17 | 1.520 (2) |
C3—H3A | 0.9500 | C16—H16A | 1.0000 |
C4—C5 | 1.382 (3) | C17—C22 | 1.387 (2) |
C4—H4A | 0.9500 | C17—C18 | 1.393 (3) |
C5—C6 | 1.394 (3) | C18—C19 | 1.381 (3) |
C5—H5A | 0.9500 | C18—H18A | 0.9500 |
C6—H6A | 0.9500 | C19—C20 | 1.388 (3) |
C7—C8 | 1.529 (2) | C19—H19A | 0.9500 |
C7—H7A | 0.9800 | C20—C21 | 1.374 (3) |
C7—H7B | 0.9800 | C20—H20A | 0.9500 |
C7—H7C | 0.9800 | C21—C22 | 1.393 (3) |
C8—C9 | 1.525 (2) | C21—H21A | 0.9500 |
C8—H8A | 1.0000 | C22—H22A | 0.9500 |
C9—C14 | 1.386 (3) | ||
O2—P1—O1 | 118.92 (7) | C10—C9—C8 | 119.47 (16) |
O2—P1—N1 | 108.63 (7) | C11—C10—C9 | 120.71 (18) |
O1—P1—N1 | 105.88 (7) | C11—C10—H10A | 119.6 |
O2—P1—C1 | 108.29 (8) | C9—C10—H10A | 119.6 |
O1—P1—C1 | 106.72 (7) | C10—C11—C12 | 120.36 (17) |
N1—P1—C1 | 107.94 (8) | C10—C11—H11A | 119.8 |
C8—N1—P1 | 120.99 (12) | C12—C11—H11A | 119.8 |
C8—N1—H1N | 115.6 (13) | C11—C12—C13 | 119.58 (18) |
P1—N1—H1N | 119.6 (13) | C11—C12—H12A | 120.2 |
C16—N2—H2A | 109.5 | C13—C12—H12A | 120.2 |
C16—N2—H2B | 109.5 | C12—C13—C14 | 119.84 (18) |
H2A—N2—H2B | 109.5 | C12—C13—H13A | 120.1 |
C16—N2—H2C | 109.5 | C14—C13—H13A | 120.1 |
H2A—N2—H2C | 109.5 | C9—C14—C13 | 121.26 (16) |
H2B—N2—H2C | 109.5 | C9—C14—H14A | 119.4 |
C6—C1—C2 | 118.55 (16) | C13—C14—H14A | 119.4 |
C6—C1—P1 | 121.47 (14) | C16—C15—H15A | 109.5 |
C2—C1—P1 | 119.95 (13) | C16—C15—H15B | 109.5 |
C3—C2—C1 | 120.62 (18) | H15A—C15—H15B | 109.5 |
C3—C2—H2D | 119.7 | C16—C15—H15C | 109.5 |
C1—C2—H2D | 119.7 | H15A—C15—H15C | 109.5 |
C4—C3—C2 | 120.10 (19) | H15B—C15—H15C | 109.5 |
C4—C3—H3A | 120.0 | N2—C16—C17 | 110.04 (14) |
C2—C3—H3A | 120.0 | N2—C16—C15 | 108.16 (13) |
C5—C4—C3 | 119.62 (18) | C17—C16—C15 | 115.83 (14) |
C5—C4—H4A | 120.2 | N2—C16—H16A | 107.5 |
C3—C4—H4A | 120.2 | C17—C16—H16A | 107.5 |
C4—C5—C6 | 120.46 (19) | C15—C16—H16A | 107.5 |
C4—C5—H5A | 119.8 | C22—C17—C18 | 118.56 (16) |
C6—C5—H5A | 119.8 | C22—C17—C16 | 122.74 (16) |
C1—C6—C5 | 120.64 (18) | C18—C17—C16 | 118.71 (15) |
C1—C6—H6A | 119.7 | C19—C18—C17 | 121.06 (18) |
C5—C6—H6A | 119.7 | C19—C18—H18A | 119.5 |
C8—C7—H7A | 109.5 | C17—C18—H18A | 119.5 |
C8—C7—H7B | 109.5 | C18—C19—C20 | 119.9 (2) |
H7A—C7—H7B | 109.5 | C18—C19—H19A | 120.1 |
C8—C7—H7C | 109.5 | C20—C19—H19A | 120.1 |
H7A—C7—H7C | 109.5 | C21—C20—C19 | 119.66 (19) |
H7B—C7—H7C | 109.5 | C21—C20—H20A | 120.2 |
N1—C8—C9 | 111.72 (14) | C19—C20—H20A | 120.2 |
N1—C8—C7 | 110.33 (14) | C20—C21—C22 | 120.56 (18) |
C9—C8—C7 | 113.45 (15) | C20—C21—H21A | 119.7 |
N1—C8—H8A | 107.0 | C22—C21—H21A | 119.7 |
C9—C8—H8A | 107.0 | C17—C22—C21 | 120.28 (18) |
C7—C8—H8A | 107.0 | C17—C22—H22A | 119.9 |
C14—C9—C10 | 118.23 (16) | C21—C22—H22A | 119.9 |
C14—C9—C8 | 122.30 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 (1) | 2.22 (1) | 3.0576 (19) | 163 (2) |
N2—H2A···O2i | 0.91 | 1.95 | 2.7733 (18) | 149 |
N2—H2B···O1 | 0.91 | 1.80 | 2.7058 (18) | 172 |
N2—H2C···O1ii | 0.91 | 1.85 | 2.7340 (17) | 163 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z. |
C8H12N+·C12H10O2P− | F(000) = 720 |
Mr = 339.35 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0483 (1) Å | Cell parameters from 8313 reflections |
b = 18.8540 (5) Å | θ = 2.5–27.5° |
c = 15.4364 (5) Å | µ = 0.17 mm−1 |
β = 97.231 (1)° | T = 100 K |
V = 1746.28 (8) Å3 | Block, clear colourless |
Z = 4 | 0.12 × 0.1 × 0.1 mm |
Bruker D8 Venture diffractometer | 3565 independent reflections |
Radiation source: high brilliance microfocus sealed tube | 2819 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.044 |
φ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −7→7 |
Tmin = 0.662, Tmax = 0.746 | k = −23→20 |
11792 measured reflections | l = −17→19 |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0362P)2 + 0.9756P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3565 reflections | Δρmax = 0.38 e Å−3 |
227 parameters | Δρmin = −0.44 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 | ||
C1 | 0.1896 (3) | 0.55594 (9) | 0.24611 (11) | 0.0133 (4) | |
O1 | 0.2613 (2) | 0.55658 (7) | 0.42213 (8) | 0.0157 (3) | |
P1 | 0.11183 (8) | 0.59115 (2) | 0.34817 (3) | 0.01203 (13) | |
C2 | 0.0448 (3) | 0.50911 (10) | 0.19710 (12) | 0.0186 (4) | |
H2 | −0.0935 | 0.4974 | 0.2165 | 0.022* | |
O2 | −0.1347 (2) | 0.58177 (7) | 0.34598 (8) | 0.0166 (3) | |
C3 | 0.1004 (3) | 0.47955 (11) | 0.12041 (13) | 0.0233 (5) | |
H3 | 0.0000 | 0.4480 | 0.0875 | 0.028* | |
C4 | 0.3027 (3) | 0.49613 (11) | 0.09177 (13) | 0.0218 (4) | |
H4 | 0.3414 | 0.4758 | 0.0394 | 0.026* | |
C5 | 0.4478 (3) | 0.54239 (10) | 0.13975 (13) | 0.0196 (4) | |
H5 | 0.5860 | 0.5539 | 0.1200 | 0.023* | |
C6 | 0.3925 (3) | 0.57220 (10) | 0.21681 (12) | 0.0153 (4) | |
H6 | 0.4934 | 0.6037 | 0.2495 | 0.018* | |
C7 | 0.1784 (3) | 0.68466 (10) | 0.34784 (11) | 0.0128 (4) | |
C8 | 0.3891 (3) | 0.70912 (10) | 0.38182 (12) | 0.0163 (4) | |
H8 | 0.4998 | 0.6765 | 0.4060 | 0.020* | |
C9 | 0.4377 (3) | 0.78129 (10) | 0.38046 (13) | 0.0190 (4) | |
H9 | 0.5817 | 0.7978 | 0.4032 | 0.023* | |
C10 | 0.2758 (3) | 0.82892 (10) | 0.34591 (12) | 0.0185 (4) | |
H10 | 0.3087 | 0.8782 | 0.3456 | 0.022* | |
C11 | 0.0660 (3) | 0.80514 (10) | 0.31172 (12) | 0.0191 (4) | |
H11 | −0.0440 | 0.8380 | 0.2875 | 0.023* | |
C12 | 0.0170 (3) | 0.73318 (10) | 0.31290 (12) | 0.0165 (4) | |
H12 | −0.1271 | 0.7169 | 0.2898 | 0.020* | |
N1 | 0.3728 (3) | 0.52482 (8) | 0.59635 (10) | 0.0140 (3) | |
H1A | 0.316 (3) | 0.5395 (11) | 0.5425 (11) | 0.017* | |
H1B | 0.275 (3) | 0.4924 (10) | 0.6153 (13) | 0.017* | |
H1C | 0.497 (3) | 0.4996 (10) | 0.5901 (13) | 0.017* | |
C13 | 0.4157 (3) | 0.58479 (10) | 0.65881 (12) | 0.0156 (4) | |
H13A | 0.4882 | 0.5662 | 0.7154 | 0.019* | |
H13B | 0.2716 | 0.6061 | 0.6689 | 0.019* | |
C14 | 0.5616 (3) | 0.64174 (10) | 0.62711 (11) | 0.0143 (4) | |
C15 | 0.5115 (3) | 0.71268 (10) | 0.64020 (12) | 0.0175 (4) | |
H15 | 0.3828 | 0.7246 | 0.6666 | 0.021* | |
C16 | 0.6477 (3) | 0.76609 (10) | 0.61505 (12) | 0.0192 (4) | |
H16 | 0.6109 | 0.8142 | 0.6249 | 0.023* | |
C17 | 0.8367 (3) | 0.75089 (10) | 0.57578 (12) | 0.0170 (4) | |
C18 | 0.9852 (3) | 0.80966 (10) | 0.55062 (13) | 0.0230 (5) | |
H18A | 1.0674 | 0.8303 | 0.6034 | 0.035* | |
H18B | 0.8939 | 0.8464 | 0.5187 | 0.035* | |
H18C | 1.0908 | 0.7905 | 0.5134 | 0.035* | |
C19 | 0.8846 (3) | 0.67987 (10) | 0.56126 (12) | 0.0164 (4) | |
H19 | 1.0111 | 0.6681 | 0.5334 | 0.020* | |
C20 | 0.7502 (3) | 0.62596 (10) | 0.58698 (12) | 0.0168 (4) | |
H20 | 0.7870 | 0.5779 | 0.5772 | 0.020* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0151 (9) | 0.0122 (9) | 0.0120 (9) | 0.0007 (7) | −0.0007 (7) | 0.0041 (7) |
O1 | 0.0191 (7) | 0.0138 (6) | 0.0143 (7) | 0.0014 (5) | 0.0026 (5) | 0.0023 (5) |
P1 | 0.0122 (2) | 0.0110 (2) | 0.0130 (2) | −0.00091 (18) | 0.00157 (17) | 0.00126 (18) |
C2 | 0.0188 (10) | 0.0176 (10) | 0.0201 (10) | −0.0034 (8) | 0.0051 (8) | 0.0004 (8) |
O2 | 0.0136 (7) | 0.0166 (7) | 0.0201 (7) | −0.0033 (5) | 0.0038 (5) | 0.0004 (5) |
C3 | 0.0290 (11) | 0.0212 (10) | 0.0198 (10) | −0.0084 (9) | 0.0038 (9) | −0.0042 (8) |
C4 | 0.0299 (11) | 0.0198 (10) | 0.0174 (10) | −0.0011 (9) | 0.0093 (8) | −0.0015 (8) |
C5 | 0.0186 (10) | 0.0184 (10) | 0.0229 (11) | 0.0010 (8) | 0.0078 (8) | 0.0031 (8) |
C6 | 0.0139 (9) | 0.0157 (9) | 0.0158 (9) | 0.0004 (7) | 0.0001 (7) | 0.0020 (7) |
C7 | 0.0141 (9) | 0.0138 (9) | 0.0109 (9) | −0.0007 (7) | 0.0030 (7) | 0.0006 (7) |
C8 | 0.0161 (9) | 0.0168 (9) | 0.0158 (9) | 0.0007 (8) | 0.0014 (7) | 0.0029 (8) |
C9 | 0.0173 (10) | 0.0202 (10) | 0.0195 (10) | −0.0071 (8) | 0.0025 (8) | −0.0011 (8) |
C10 | 0.0287 (11) | 0.0126 (9) | 0.0154 (10) | −0.0031 (8) | 0.0075 (8) | −0.0001 (7) |
C11 | 0.0245 (11) | 0.0157 (10) | 0.0174 (10) | 0.0048 (8) | 0.0029 (8) | 0.0026 (8) |
C12 | 0.0162 (9) | 0.0184 (9) | 0.0146 (9) | 0.0013 (8) | 0.0015 (7) | 0.0001 (8) |
N1 | 0.0146 (8) | 0.0131 (8) | 0.0144 (8) | 0.0003 (6) | 0.0028 (6) | 0.0022 (6) |
C13 | 0.0182 (10) | 0.0150 (9) | 0.0139 (9) | −0.0009 (8) | 0.0034 (7) | −0.0007 (7) |
C14 | 0.0170 (9) | 0.0165 (9) | 0.0089 (9) | 0.0006 (8) | 0.0002 (7) | 0.0003 (7) |
C15 | 0.0188 (10) | 0.0195 (10) | 0.0144 (10) | 0.0017 (8) | 0.0035 (8) | −0.0002 (8) |
C16 | 0.0261 (11) | 0.0127 (9) | 0.0185 (10) | 0.0030 (8) | 0.0020 (8) | −0.0015 (8) |
C17 | 0.0206 (10) | 0.0181 (10) | 0.0114 (9) | −0.0030 (8) | −0.0020 (7) | −0.0004 (7) |
C18 | 0.0267 (11) | 0.0194 (10) | 0.0228 (11) | −0.0068 (9) | 0.0025 (9) | 0.0015 (8) |
C19 | 0.0148 (9) | 0.0195 (10) | 0.0150 (9) | −0.0010 (8) | 0.0028 (7) | −0.0008 (8) |
C20 | 0.0192 (10) | 0.0137 (9) | 0.0171 (10) | 0.0018 (8) | 0.0010 (8) | −0.0004 (7) |
C1—P1 | 1.8248 (18) | C11—C12 | 1.389 (3) |
C1—C2 | 1.397 (3) | C12—H12 | 0.9500 |
C1—C6 | 1.394 (3) | N1—H1A | 0.902 (15) |
O1—P1 | 1.5118 (13) | N1—H1B | 0.922 (15) |
P1—O2 | 1.4979 (13) | N1—H1C | 0.905 (15) |
P1—C7 | 1.8088 (18) | N1—C13 | 1.487 (2) |
C2—H2 | 0.9500 | C13—H13A | 0.9900 |
C2—C3 | 1.387 (3) | C13—H13B | 0.9900 |
C3—H3 | 0.9500 | C13—C14 | 1.510 (3) |
C3—C4 | 1.388 (3) | C14—C15 | 1.392 (3) |
C4—H4 | 0.9500 | C14—C20 | 1.397 (3) |
C4—C5 | 1.384 (3) | C15—H15 | 0.9500 |
C5—H5 | 0.9500 | C15—C16 | 1.387 (3) |
C5—C6 | 1.394 (3) | C16—H16 | 0.9500 |
C6—H6 | 0.9500 | C16—C17 | 1.390 (3) |
C7—C8 | 1.394 (3) | C17—C18 | 1.508 (3) |
C7—C12 | 1.396 (3) | C17—C19 | 1.394 (3) |
C8—H8 | 0.9500 | C18—H18A | 0.9800 |
C8—C9 | 1.393 (3) | C18—H18B | 0.9800 |
C9—H9 | 0.9500 | C18—H18C | 0.9800 |
C9—C10 | 1.385 (3) | C19—H19 | 0.9500 |
C10—H10 | 0.9500 | C19—C20 | 1.390 (3) |
C10—C11 | 1.386 (3) | C20—H20 | 0.9500 |
C11—H11 | 0.9500 | ||
C2—C1—P1 | 119.04 (14) | C7—C12—H12 | 119.8 |
C6—C1—P1 | 122.21 (14) | C11—C12—C7 | 120.32 (18) |
C6—C1—C2 | 118.71 (17) | C11—C12—H12 | 119.8 |
O1—P1—C1 | 107.49 (8) | H1A—N1—H1B | 108.2 (18) |
O1—P1—C7 | 108.06 (8) | H1A—N1—H1C | 106.7 (18) |
O2—P1—C1 | 107.55 (8) | H1B—N1—H1C | 105.0 (18) |
O2—P1—O1 | 117.71 (7) | C13—N1—H1A | 112.2 (13) |
O2—P1—C7 | 109.66 (8) | C13—N1—H1B | 111.3 (13) |
C7—P1—C1 | 105.69 (8) | C13—N1—H1C | 112.9 (13) |
C1—C2—H2 | 119.6 | N1—C13—H13A | 109.0 |
C3—C2—C1 | 120.90 (18) | N1—C13—H13B | 109.0 |
C3—C2—H2 | 119.6 | N1—C13—C14 | 113.08 (15) |
C2—C3—H3 | 120.0 | H13A—C13—H13B | 107.8 |
C2—C3—C4 | 119.94 (18) | C14—C13—H13A | 109.0 |
C4—C3—H3 | 120.0 | C14—C13—H13B | 109.0 |
C3—C4—H4 | 120.1 | C15—C14—C13 | 119.31 (16) |
C5—C4—C3 | 119.77 (18) | C15—C14—C20 | 118.30 (17) |
C5—C4—H4 | 120.1 | C20—C14—C13 | 122.37 (16) |
C4—C5—H5 | 119.8 | C14—C15—H15 | 119.7 |
C4—C5—C6 | 120.43 (18) | C16—C15—C14 | 120.61 (17) |
C6—C5—H5 | 119.8 | C16—C15—H15 | 119.7 |
C1—C6—H6 | 119.9 | C15—C16—H16 | 119.2 |
C5—C6—C1 | 120.24 (17) | C15—C16—C17 | 121.50 (18) |
C5—C6—H6 | 119.9 | C17—C16—H16 | 119.2 |
C8—C7—P1 | 120.99 (14) | C16—C17—C18 | 120.67 (17) |
C8—C7—C12 | 119.37 (17) | C16—C17—C19 | 117.86 (17) |
C12—C7—P1 | 119.64 (14) | C19—C17—C18 | 121.46 (17) |
C7—C8—H8 | 119.9 | C17—C18—H18A | 109.5 |
C9—C8—C7 | 120.13 (18) | C17—C18—H18B | 109.5 |
C9—C8—H8 | 119.9 | C17—C18—H18C | 109.5 |
C8—C9—H9 | 120.0 | H18A—C18—H18B | 109.5 |
C10—C9—C8 | 119.94 (18) | H18A—C18—H18C | 109.5 |
C10—C9—H9 | 120.0 | H18B—C18—H18C | 109.5 |
C9—C10—H10 | 119.8 | C17—C19—H19 | 119.5 |
C9—C10—C11 | 120.39 (18) | C20—C19—C17 | 121.03 (17) |
C11—C10—H10 | 119.8 | C20—C19—H19 | 119.5 |
C10—C11—H11 | 120.1 | C14—C20—H20 | 119.7 |
C10—C11—C12 | 119.84 (18) | C19—C20—C14 | 120.69 (17) |
C12—C11—H11 | 120.1 | C19—C20—H20 | 119.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.90 (2) | 1.87 (2) | 2.755 (2) | 165 (2) |
N1—H1B···O2i | 0.92 (2) | 1.78 (2) | 2.688 (2) | 168 (2) |
N1—H1C···O1ii | 0.91 (2) | 1.83 (2) | 2.738 (2) | 177 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |