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The N—H
O hydrogen bond is the characteristic interaction in the crystal structures of
N-benzyl-
P-phenyl-
N′-(
p-tolyl)phosphonic diamide, C
20H
21N
2OP or (C
6H
5)P(O)(NHCH
2C
6H
5)(NHC
6H
4-
p-CH
3), (I), diphenylphosphinic 1-methylpropylamide, C
16H
20NOP or (C
6H
5)
2P(O)[NHCH(CH
3)(C
2H
5)], (II), (
S)-1-phenylethylammonium
N-[(
S)-1-phenylethyl]phenylphosphonamidate, C
8H
12N
+·C
14H
15NO
2P
− or [
S-(C
6H
5)CH(CH
3)NH
3][(C
6H
5)P(O){
S-NHCH(CH
3)(C
6H
5)}(O)], (III), and (4-methylbenzyl)ammonium diphenylphosphinate, C
8H
12N
+·C
12H
10O
2P
− or [4-CH
3-C
6H
4CH
2NH
3][(C
6H
5)
2P(O)(O)], (IV). This article focuses on the N—H
O hydrogen bonds by considering the structures of (I), (II), (III) and (IV), and reviewing their analogous compounds, including 43 (C)P(O)(N)
2, 102 (C)
2P(O)(N), 31 (C)P(O)(N)(O) and 96 (C)
2P(O)(O) structures, deposited in the Cambridge Structural Database (CSD). For the structures with a (C)P(O)(N)
2 segment, only neutral hydrogen bonds were found in the CSD. The other three classes of compounds included both neutral and `charge-assisted' hydrogen bonds, and the (C)
2P(O)(O) structures were particularly noticeable for a high number of cation–anion compounds. The overall tendencies of N
O distances in neutral and cation–anion compounds were compared. The N—H
O hydrogen-bond angles were also analyzed for the four classes of phosphorus compounds.
Supporting information
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.
(I)
N-Benzyl-
P-phenyl-
N'-(
p-tolyl)phosphonic
diamide
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
(II) Diphenylphosphinic 1-methylpropylamide
top
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 | | |
Hydrogen-bond geometry (Å, º) top
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. |
(III) (
S)-1-Phenylethylammonium
N-[(
S)-1-phenylethyl]phenylphosphonamidate
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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. |
(fh24) (4-Methylbenzyl)ammonium diphenylphosphinate
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
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