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The crystal structures of diphenyl (cycloheptylamido)phosphate, C
19H
24NO
3P or (C
6H
5O)
2P(O)(NHC
7H
13), (
I), and diphenyl (dibenzylamido)phosphate, C
26H
24NO
3P or (C
6H
5O)
2P(O)[N(CH
2C
6H
5)
2], (
II), are reported. The NHC
7H
13 group in (
I) provides two significant hydrogen-donor sites in N—H
O and C—H
O hydrogen bonds, needed for a one-dimensional hydrogen-bond pattern along [100] in the crystal, while (
II), with a (C
6H
5CH
2)
2N moiety, lacks these hydrogen bonds, but its three-dimensional supramolecular structure is mediated by C—H
π interactions. The conformational behaviour of the phenyl rings in (
I), (
II) and analogous structures from the Cambridge Structural Database (CSD) were studied in terms of flexibility, volume of the other group attached to phosphorus and packing forces. From this study, synclinal (±
sc), anticlinal (±
ac) and antiperiplanar (±
ap) conformations were found to occur. In the structure of (
II), there is an intramolecular C
ortho—H
O interaction that imposes a +
sc conformation for the phenyl ring involved. For the structures from the CSD, the +
sc and ±
ap conformations appear to be mainly imposed by similar C
ortho—H
O intramolecular interactions. The large contribution of the C
H/H
C contacts (32.3%) in the two-dimensional fingerprint plots of (
II) is a result of the C—H
π interactions. The differential scanning calorimetry (DSC) analyses exhibit peak temperatures (
Tm) at 109 and 81 °C for (
I) and (
II), respectively, which agree with the strengths of the intermolecular contacts and the melting points.
Supporting information
CCDC references: 1971119; 1895358
Data collection: CrysAlis PRO (Rigaku OD, 2015) for (I); Rigaku CrystalClear-SM Expert (Rigaku, 2011) for (II). For both structures, cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (I); SHELXT2014 (Sheldrick, 2015a) for (II). Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for (I); SHELXL2018 (Sheldrick, 2015b) for (II). For both structures, molecular graphics: CAMERON (Watkin et al., 1996) and pyMOL (Schrödinger, 2015). Software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) for (I); SHELXL2018 (Sheldrick, 2015b) for (II).
Diphenyl (cycloheptylamido)phosphate (I)
top
Crystal data top
C19H24NO3P | F(000) = 736 |
Mr = 345.36 | Dx = 1.295 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3874 reflections |
a = 9.3538 (2) Å | θ = 2.1–27.1° |
b = 9.7899 (3) Å | µ = 0.17 mm−1 |
c = 19.3432 (5) Å | T = 175 K |
V = 1771.31 (5) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.25 × 0.15 mm |
Data collection top
Rigaku Xcalibur Sapphire3 Gemini diffractometer | 3411 independent reflections |
Graphite monochromator | 2964 reflections with I > 2.0σ(I) |
Detector resolution: 16.0143 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 28.0°, θmin = 2.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −7→12 |
Tmin = 0.979, Tmax = 1.000 | k = −9→11 |
9026 measured reflections | l = −23→23 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.052 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince,
1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
19.6 25.7 7.98 |
wR(F2) = 0.103 | (Δ/σ)max = 0.001 |
S = 0.95 | Δρmax = 0.32 e Å−3 |
3338 reflections | Δρmin = −0.54 e Å−3 |
221 parameters | Absolute structure: Flack (1983), 1505 Friedel-pairs |
79 restraints | Absolute structure parameter: 0.6 (3) |
Primary atom site location: iterative | |
Special details top
Experimental. The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. |
Refinement. Data collection and crystal screening for (I) was performed
on a Rigaku Oxford-Diffraction Gemini-S diffractometer with sealed-tube
Mo-Kα radiation using the CrysAlisPro program (Rigaku
Oxford-Diffraction, 2012). This program was also used for
the integration of
the data using default parameters, for the empirical absorption correction
using spherical harmonics employing symmetry-equivalent and redundant data,
and the correction for Lorentz and polarization effects. The ab-initio
iterative charge flipping method was used to solve the crystal structure of
(I) with parameters described elsewhere (van der Lee, 2013)
employing
the Superflip program (Palatinus&Chapuis, 2007)
and it was refined
using full-matrix least-squares procedures on squared structure factor
amplitudes F2 as implemented in CRYSTALS (Betteridge et
al., 2003) using all independent reflections with
I>0. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.35676 (6) | 0.84662 (6) | 0.00163 (13) | 0.0183 | |
O2 | 0.4415 (4) | 0.9225 (3) | 0.06247 (18) | 0.0205 | |
C3 | 0.4113 (6) | 0.8932 (5) | 0.1321 (3) | 0.0257 | |
C4 | 0.4887 (6) | 0.7907 (5) | 0.1653 (2) | 0.0305 | |
C5 | 0.4633 (8) | 0.7722 (6) | 0.2345 (3) | 0.0433 | |
C6 | 0.3634 (7) | 0.8486 (7) | 0.2706 (3) | 0.0431 | |
C7 | 0.2905 (8) | 0.9495 (7) | 0.2365 (3) | 0.0406 | |
C8 | 0.3173 (7) | 0.9711 (6) | 0.1665 (3) | 0.0333 | |
H81 | 0.2689 | 1.0405 | 0.1435 | 0.0500* | |
H71 | 0.2237 | 1.0015 | 0.2605 | 0.0500* | |
H61 | 0.3472 | 0.8316 | 0.3172 | 0.0500* | |
H51 | 0.5151 | 0.7058 | 0.2580 | 0.0500* | |
H41 | 0.5550 | 0.7374 | 0.1417 | 0.0500* | |
O9 | 0.20228 (18) | 0.87095 (18) | 0.0010 (3) | 0.0275 | |
O10 | 0.4444 (4) | 0.9209 (4) | −0.0573 (2) | 0.0288 | |
C11 | 0.4140 (5) | 0.8929 (5) | −0.1266 (3) | 0.0223 | |
C12 | 0.3098 (6) | 0.9729 (6) | −0.1603 (3) | 0.0323 | |
C13 | 0.2900 (8) | 0.9499 (8) | −0.2298 (3) | 0.0459 | |
C14 | 0.3672 (7) | 0.8504 (7) | −0.2635 (4) | 0.0488 | |
C15 | 0.4657 (7) | 0.7703 (7) | −0.2302 (3) | 0.0420 | |
C16 | 0.4909 (7) | 0.7958 (6) | −0.1596 (2) | 0.0358 | |
H161 | 0.5592 | 0.7455 | −0.1357 | 0.0500* | |
H151 | 0.5141 | 0.7017 | −0.2538 | 0.0500* | |
H141 | 0.3519 | 0.8376 | −0.3106 | 0.0500* | |
H131 | 0.2239 | 1.0023 | −0.2540 | 0.0500* | |
N17 | 0.3982 (2) | 0.6874 (2) | 0.0026 (3) | 0.0213 | |
C18 | 0.2936 (3) | 0.5742 (2) | 0.0018 (3) | 0.0232 | |
C19 | 0.3086 (7) | 0.4933 (6) | 0.0682 (3) | 0.0425 | |
C20 | 0.4369 (7) | 0.3947 (6) | 0.0702 (3) | 0.0671 | |
C21 | 0.4344 (6) | 0.2720 (4) | 0.0185 (3) | 0.0809 | |
C22 | 0.4727 (8) | 0.2979 (6) | −0.0558 (3) | 0.0828 | |
C23 | 0.4388 (6) | 0.4358 (5) | −0.0842 (3) | 0.0460 | |
C24 | 0.2980 (6) | 0.4913 (5) | −0.0638 (3) | 0.0330 | |
H241 | 0.2705 | 0.5513 | −0.1015 | 0.0500* | |
H242 | 0.2268 | 0.4196 | −0.0609 | 0.0500* | |
H231 | 0.4456 | 0.4317 | −0.1342 | 0.0500* | |
H232 | 0.5135 | 0.4971 | −0.0684 | 0.0500* | |
H191 | 0.2225 | 0.4394 | 0.0742 | 0.0500* | |
H192 | 0.3146 | 0.5558 | 0.1070 | 0.0500* | |
H181 | 0.1988 | 0.6165 | 0.0040 | 0.0500* | |
H201 | 0.5191 | 0.4478 | 0.0598 | 0.0830* | |
H202 | 0.4452 | 0.3584 | 0.1155 | 0.0830* | |
H211 | 0.4991 | 0.2058 | 0.0360 | 0.1300* | |
H212 | 0.3399 | 0.2364 | 0.0198 | 0.1300* | |
H221 | 0.5721 | 0.2813 | −0.0614 | 0.1047* | |
H222 | 0.4199 | 0.2331 | −0.0820 | 0.1047* | |
H121 | 0.2592 | 1.0429 | −0.1367 | 0.0436* | |
H171 | 0.484 (2) | 0.6673 (19) | −0.009 (2) | 0.0300* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0138 (3) | 0.0183 (3) | 0.0227 (3) | −0.0001 (2) | 0.0006 (7) | −0.0007 (6) |
O2 | 0.0227 (17) | 0.0164 (13) | 0.0223 (15) | −0.0076 (15) | −0.0063 (14) | −0.0020 (13) |
C3 | 0.029 (3) | 0.028 (2) | 0.020 (2) | −0.011 (2) | 0.002 (2) | −0.007 (2) |
C4 | 0.029 (3) | 0.024 (2) | 0.039 (3) | 0.008 (2) | −0.011 (2) | −0.003 (2) |
C5 | 0.055 (5) | 0.042 (3) | 0.033 (3) | 0.005 (3) | −0.014 (3) | 0.002 (3) |
C6 | 0.058 (5) | 0.055 (4) | 0.016 (3) | −0.018 (3) | 0.004 (3) | 0.003 (2) |
C7 | 0.045 (4) | 0.044 (3) | 0.033 (3) | 0.005 (3) | 0.018 (3) | −0.015 (3) |
C8 | 0.037 (3) | 0.034 (3) | 0.029 (3) | 0.006 (2) | 0.010 (2) | −0.007 (2) |
O9 | 0.0155 (8) | 0.0237 (9) | 0.0434 (11) | 0.0019 (7) | −0.004 (2) | −0.006 (2) |
O10 | 0.027 (2) | 0.0371 (17) | 0.0223 (15) | −0.0064 (19) | −0.0090 (16) | 0.0040 (15) |
C11 | 0.016 (3) | 0.026 (2) | 0.025 (2) | −0.003 (2) | 0.002 (2) | 0.003 (2) |
C12 | 0.023 (3) | 0.034 (3) | 0.040 (3) | −0.003 (2) | 0.003 (2) | 0.005 (3) |
C13 | 0.038 (4) | 0.058 (4) | 0.042 (3) | −0.011 (4) | −0.011 (3) | 0.012 (3) |
C14 | 0.043 (5) | 0.069 (5) | 0.034 (4) | −0.011 (3) | −0.009 (3) | 0.015 (3) |
C15 | 0.039 (4) | 0.055 (4) | 0.032 (3) | −0.008 (3) | 0.005 (3) | −0.010 (3) |
C16 | 0.036 (3) | 0.052 (3) | 0.020 (3) | −0.004 (3) | −0.008 (2) | 0.004 (2) |
N17 | 0.0128 (9) | 0.0206 (10) | 0.0305 (12) | 0.0018 (8) | 0.003 (3) | −0.006 (2) |
C18 | 0.0189 (12) | 0.0192 (12) | 0.0316 (13) | −0.0034 (10) | 0.008 (2) | 0.001 (2) |
C19 | 0.057 (3) | 0.040 (2) | 0.030 (2) | −0.018 (2) | 0.011 (3) | 0.007 (2) |
C20 | 0.056 (3) | 0.071 (3) | 0.074 (3) | −0.007 (3) | −0.019 (3) | 0.047 (2) |
C21 | 0.058 (3) | 0.0235 (17) | 0.161 (4) | 0.0095 (18) | 0.021 (4) | 0.037 (2) |
C22 | 0.065 (4) | 0.052 (2) | 0.131 (4) | 0.018 (3) | 0.001 (3) | −0.013 (2) |
C23 | 0.039 (2) | 0.053 (2) | 0.046 (2) | 0.002 (2) | −0.002 (2) | −0.0226 (17) |
C24 | 0.029 (2) | 0.036 (2) | 0.034 (2) | −0.006 (2) | −0.001 (2) | −0.0073 (19) |
Geometric parameters (Å, º) top
P1—O2 | 1.601 (3) | C15—C16 | 1.409 (6) |
P1—O9 | 1.4645 (18) | C15—H151 | 0.930 |
P1—O10 | 1.581 (4) | C16—H161 | 0.930 |
P1—N17 | 1.607 (2) | N17—C18 | 1.479 (3) |
O2—C3 | 1.405 (6) | N17—H171 | 0.860 (18) |
C3—C4 | 1.394 (6) | C18—C19 | 1.514 (6) |
C3—C8 | 1.341 (7) | C18—C24 | 1.507 (6) |
C4—C5 | 1.371 (6) | C18—H181 | 0.980 |
C4—H41 | 0.930 | C19—C20 | 1.540 (7) |
C5—C6 | 1.385 (7) | C19—H191 | 0.970 |
C5—H51 | 0.930 | C19—H192 | 0.970 |
C6—C7 | 1.369 (7) | C20—C21 | 1.563 (6) |
C6—H61 | 0.930 | C20—H201 | 0.950 |
C7—C8 | 1.394 (6) | C20—H202 | 0.950 |
C7—H71 | 0.930 | C21—C22 | 1.502 (7) |
C8—H81 | 0.930 | C21—H211 | 0.950 |
O10—C11 | 1.399 (6) | C21—H212 | 0.950 |
C11—C12 | 1.409 (6) | C22—C23 | 1.491 (6) |
C11—C16 | 1.351 (7) | C22—H221 | 0.950 |
C12—C13 | 1.377 (6) | C22—H222 | 0.950 |
C12—H121 | 0.950 | C23—C24 | 1.478 (6) |
C13—C14 | 1.377 (7) | C23—H231 | 0.970 |
C13—H131 | 0.930 | C23—H232 | 0.970 |
C14—C15 | 1.370 (7) | C24—H241 | 0.970 |
C14—H141 | 0.930 | C24—H242 | 0.970 |
| | | |
O2—P1—O9 | 114.8 (3) | P1—N17—H171 | 116.4 (13) |
O2—P1—O10 | 93.42 (10) | C18—N17—H171 | 116.5 (13) |
O9—P1—O10 | 115.5 (3) | N17—C18—C19 | 108.8 (4) |
O2—P1—N17 | 108.8 (2) | N17—C18—C24 | 113.2 (4) |
O9—P1—N17 | 113.34 (11) | C19—C18—C24 | 115.5 (2) |
O10—P1—N17 | 109.2 (2) | N17—C18—H181 | 106.4 |
P1—O2—C3 | 120.7 (3) | C19—C18—H181 | 105.6 |
O2—C3—C4 | 118.9 (5) | C24—C18—H181 | 106.8 |
O2—C3—C8 | 119.4 (5) | C18—C19—C20 | 114.9 (5) |
C4—C3—C8 | 121.4 (5) | C18—C19—H191 | 108.0 |
C3—C4—C5 | 117.0 (5) | C20—C19—H191 | 107.6 |
C3—C4—H41 | 121.7 | C18—C19—H192 | 109.3 |
C5—C4—H41 | 121.3 | C20—C19—H192 | 109.3 |
C4—C5—C6 | 122.5 (6) | H191—C19—H192 | 107.4 |
C4—C5—H51 | 118.6 | C19—C20—C21 | 117.0 (5) |
C6—C5—H51 | 118.8 | C19—C20—H201 | 106.3 |
C5—C6—C7 | 118.9 (6) | C21—C20—H201 | 107.4 |
C5—C6—H61 | 120.2 | C19—C20—H202 | 108.8 |
C7—C6—H61 | 120.9 | C21—C20—H202 | 107.8 |
C6—C7—C8 | 119.2 (6) | H201—C20—H202 | 109.5 |
C6—C7—H71 | 119.4 | C20—C21—C22 | 118.6 (4) |
C8—C7—H71 | 121.4 | C20—C21—H211 | 106.6 |
C7—C8—C3 | 120.9 (6) | C22—C21—H211 | 107.8 |
C7—C8—H81 | 119.3 | C20—C21—H212 | 106.2 |
C3—C8—H81 | 119.8 | C22—C21—H212 | 108.0 |
P1—O10—C11 | 119.7 (3) | H211—C21—H212 | 109.5 |
O10—C11—C12 | 118.3 (5) | C21—C22—C23 | 117.0 (5) |
O10—C11—C16 | 118.8 (5) | C21—C22—H221 | 108.2 |
C12—C11—C16 | 122.8 (5) | C23—C22—H221 | 108.7 |
C11—C12—C13 | 116.9 (6) | C21—C22—H222 | 105.8 |
C11—C12—H121 | 121.6 | C23—C22—H222 | 107.4 |
C13—C12—H121 | 121.4 | H221—C22—H222 | 109.5 |
C12—C13—C14 | 120.5 (7) | C22—C23—C24 | 115.1 (5) |
C12—C13—H131 | 119.4 | C22—C23—H231 | 108.4 |
C14—C13—H131 | 120.1 | C24—C23—H231 | 109.8 |
C13—C14—C15 | 122.4 (7) | C22—C23—H232 | 106.9 |
C13—C14—H141 | 118.5 | C24—C23—H232 | 109.3 |
C15—C14—H141 | 119.1 | H231—C23—H232 | 107.1 |
C14—C15—C16 | 117.8 (6) | C18—C24—C23 | 116.5 (4) |
C14—C15—H151 | 120.6 | C18—C24—H241 | 107.4 |
C16—C15—H151 | 121.6 | C23—C24—H241 | 105.0 |
C15—C16—C11 | 119.6 (6) | C18—C24—H242 | 108.8 |
C15—C16—H161 | 120.2 | C23—C24—H242 | 111.2 |
C11—C16—H161 | 120.2 | H241—C24—H242 | 107.4 |
P1—N17—C18 | 124.57 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H232···O9i | 0.97 | 2.57 | 3.516 (8) | 166 (1) |
N17—H171···O9i | 0.86 | 2.08 | 2.901 (8) | 159 (4) |
Symmetry code: (i) x+1/2, −y+3/2, z. |
Diphenyl (dibenzylamido)phosphate (II)
top
Crystal data top
C26H24NO3P | Z = 2 |
Mr = 429.43 | F(000) = 452 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
a = 8.3404 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5349 (5) Å | Cell parameters from 7627 reflections |
c = 14.9677 (7) Å | θ = 3.7–29.8° |
α = 76.280 (4)° | µ = 0.16 mm−1 |
β = 75.778 (4)° | T = 120 K |
γ = 72.055 (4)° | Block, colourless |
V = 1080.73 (9) Å3 | 0.25 × 0.20 × 0.20 mm |
Data collection top
AFC11 (Right): Eulerian 3 circle CCD diffractometer | 3578 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.018 |
Profile data from ω–scans | θmax = 25.4°, θmin = 3.2° |
Absorption correction: multi-scan CrysAlis PRO (Rigaku OD, 2015) | h = −10→10 |
Tmin = 0.722, Tmax = 1.000 | k = −11→11 |
9523 measured reflections | l = −18→18 |
3901 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0421P)2 + 0.4112P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.021 |
3901 reflections | Δρmax = 0.27 e Å−3 |
280 parameters | Δρmin = −0.34 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. |
Refinement. Data collection and crystal screening for (I) was performed
on a Rigaku Oxford-Diffraction Gemini-S diffractometer with sealed-tube
Mo-Kα radiation using the CrysAlisPro program (Rigaku
Oxford-Diffraction, 2012). This program was also used for
the integration of
the data using default parameters, for the empirical absorption correction
using spherical harmonics employing symmetry-equivalent and redundant data,
and the correction for Lorentz and polarization effects. The ab-initio
iterative charge flipping method was used to solve the crystal structure of
(I) with parameters described elsewhere (van der Lee, 2013)
employing
the Superflip program (Palatinus&Chapuis, 2007)
and it was refined
using full-matrix least-squares procedures on squared structure factor
amplitudes F2 as implemented in CRYSTALS (Betteridge et
al., 2003) using all independent reflections with
I>0. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.28992 (4) | 0.22585 (4) | 0.24553 (2) | 0.02034 (11) | |
O1 | 0.19646 (12) | 0.25264 (11) | 0.16998 (7) | 0.0268 (2) | |
O2 | 0.18570 (12) | 0.30054 (10) | 0.33444 (6) | 0.0242 (2) | |
O3 | 0.44766 (12) | 0.29786 (10) | 0.22264 (6) | 0.0229 (2) | |
N1 | 0.35880 (14) | 0.04977 (12) | 0.28829 (7) | 0.0210 (2) | |
C1 | 0.11701 (16) | 0.45642 (14) | 0.32925 (9) | 0.0216 (3) | |
C2 | 0.13891 (17) | 0.51758 (16) | 0.39864 (9) | 0.0251 (3) | |
H2A | 0.204474 | 0.457320 | 0.444418 | 0.030* | |
C3 | 0.06359 (18) | 0.66858 (16) | 0.40047 (10) | 0.0283 (3) | |
H3A | 0.077787 | 0.712423 | 0.447789 | 0.034* | |
C4 | −0.03204 (17) | 0.75573 (15) | 0.33386 (10) | 0.0279 (3) | |
H4A | −0.083810 | 0.859051 | 0.335667 | 0.033* | |
C5 | −0.05239 (18) | 0.69265 (16) | 0.26462 (10) | 0.0287 (3) | |
H5A | −0.117877 | 0.752952 | 0.218813 | 0.034* | |
C6 | 0.02249 (17) | 0.54132 (15) | 0.26162 (10) | 0.0264 (3) | |
H6A | 0.008991 | 0.497327 | 0.214182 | 0.032* | |
C7 | 0.58266 (16) | 0.26177 (14) | 0.14702 (9) | 0.0212 (3) | |
C8 | 0.55543 (18) | 0.31321 (15) | 0.05655 (9) | 0.0244 (3) | |
H8A | 0.444962 | 0.369332 | 0.044181 | 0.029* | |
C9 | 0.69321 (19) | 0.28115 (17) | −0.01621 (10) | 0.0311 (3) | |
H9A | 0.677120 | 0.314654 | −0.079222 | 0.037* | |
C10 | 0.8537 (2) | 0.2007 (2) | 0.00263 (11) | 0.0385 (4) | |
H10A | 0.947575 | 0.179286 | −0.047458 | 0.046* | |
C11 | 0.8781 (2) | 0.1512 (2) | 0.09426 (11) | 0.0395 (4) | |
H11A | 0.988814 | 0.096637 | 0.106884 | 0.047* | |
C12 | 0.74155 (18) | 0.18102 (16) | 0.16751 (10) | 0.0287 (3) | |
H12A | 0.756938 | 0.146579 | 0.230603 | 0.034* | |
C13 | 0.31490 (17) | −0.06607 (15) | 0.25673 (9) | 0.0241 (3) | |
H13A | 0.224230 | −0.017085 | 0.218789 | 0.029* | |
H13B | 0.267326 | −0.131358 | 0.312238 | 0.029* | |
C14 | 0.46539 (17) | −0.16227 (15) | 0.19938 (9) | 0.0227 (3) | |
C15 | 0.55410 (18) | −0.09884 (15) | 0.11602 (10) | 0.0256 (3) | |
H15A | 0.524078 | 0.006721 | 0.096448 | 0.031* | |
C16 | 0.68566 (19) | −0.18823 (18) | 0.06139 (11) | 0.0334 (3) | |
H16A | 0.744928 | −0.144031 | 0.004279 | 0.040* | |
C17 | 0.7312 (2) | −0.34247 (19) | 0.08992 (12) | 0.0399 (4) | |
H17A | 0.821881 | −0.403902 | 0.052550 | 0.048* | |
C18 | 0.6445 (2) | −0.40617 (17) | 0.17262 (13) | 0.0389 (4) | |
H18A | 0.675686 | −0.511682 | 0.192324 | 0.047* | |
C19 | 0.5118 (2) | −0.31677 (15) | 0.22719 (11) | 0.0302 (3) | |
H19A | 0.452266 | −0.361485 | 0.284001 | 0.036* | |
C20 | 0.47160 (16) | −0.00427 (14) | 0.35785 (9) | 0.0215 (3) | |
H20A | 0.491704 | 0.082604 | 0.374481 | 0.026* | |
H20B | 0.583807 | −0.065766 | 0.329936 | 0.026* | |
C21 | 0.39591 (16) | −0.09676 (14) | 0.44588 (9) | 0.0209 (3) | |
C22 | 0.48106 (18) | −0.24494 (16) | 0.47433 (10) | 0.0274 (3) | |
H22A | 0.589320 | −0.288210 | 0.439166 | 0.033* | |
C23 | 0.4090 (2) | −0.33073 (16) | 0.55406 (11) | 0.0327 (3) | |
H23A | 0.468936 | −0.431673 | 0.573441 | 0.039* | |
C24 | 0.2508 (2) | −0.26933 (17) | 0.60496 (10) | 0.0303 (3) | |
H24A | 0.200719 | −0.328244 | 0.658723 | 0.036* | |
C25 | 0.16556 (18) | −0.12152 (17) | 0.57722 (10) | 0.0281 (3) | |
H25A | 0.056824 | −0.078855 | 0.612209 | 0.034* | |
C26 | 0.23788 (17) | −0.03546 (15) | 0.49876 (9) | 0.0242 (3) | |
H26A | 0.179122 | 0.066360 | 0.480840 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01953 (18) | 0.02070 (19) | 0.01905 (18) | −0.00377 (13) | −0.00332 (13) | −0.00256 (13) |
O1 | 0.0258 (5) | 0.0293 (5) | 0.0242 (5) | −0.0051 (4) | −0.0080 (4) | −0.0022 (4) |
O2 | 0.0241 (5) | 0.0209 (5) | 0.0218 (5) | −0.0006 (4) | −0.0015 (4) | −0.0026 (4) |
O3 | 0.0243 (5) | 0.0224 (5) | 0.0217 (5) | −0.0070 (4) | −0.0007 (4) | −0.0062 (4) |
N1 | 0.0220 (5) | 0.0211 (6) | 0.0214 (5) | −0.0054 (4) | −0.0068 (4) | −0.0039 (4) |
C1 | 0.0166 (6) | 0.0214 (6) | 0.0229 (6) | −0.0039 (5) | 0.0013 (5) | −0.0032 (5) |
C2 | 0.0198 (6) | 0.0310 (7) | 0.0223 (7) | −0.0059 (5) | −0.0021 (5) | −0.0035 (6) |
C3 | 0.0255 (7) | 0.0319 (7) | 0.0292 (7) | −0.0098 (6) | −0.0009 (6) | −0.0103 (6) |
C4 | 0.0235 (7) | 0.0232 (7) | 0.0357 (8) | −0.0059 (5) | −0.0017 (6) | −0.0072 (6) |
C5 | 0.0257 (7) | 0.0253 (7) | 0.0316 (8) | −0.0027 (6) | −0.0077 (6) | −0.0014 (6) |
C6 | 0.0260 (7) | 0.0261 (7) | 0.0265 (7) | −0.0038 (6) | −0.0065 (6) | −0.0059 (6) |
C7 | 0.0236 (7) | 0.0189 (6) | 0.0220 (6) | −0.0085 (5) | −0.0007 (5) | −0.0056 (5) |
C8 | 0.0256 (7) | 0.0230 (7) | 0.0251 (7) | −0.0087 (5) | −0.0058 (5) | −0.0012 (5) |
C9 | 0.0336 (8) | 0.0394 (8) | 0.0220 (7) | −0.0149 (6) | −0.0033 (6) | −0.0039 (6) |
C10 | 0.0283 (8) | 0.0575 (10) | 0.0280 (8) | −0.0113 (7) | 0.0033 (6) | −0.0130 (7) |
C11 | 0.0228 (7) | 0.0564 (10) | 0.0349 (8) | −0.0029 (7) | −0.0048 (6) | −0.0100 (7) |
C12 | 0.0274 (7) | 0.0349 (8) | 0.0237 (7) | −0.0071 (6) | −0.0068 (6) | −0.0045 (6) |
C13 | 0.0262 (7) | 0.0250 (7) | 0.0248 (7) | −0.0112 (5) | −0.0067 (5) | −0.0035 (5) |
C14 | 0.0272 (7) | 0.0221 (6) | 0.0236 (7) | −0.0088 (5) | −0.0105 (5) | −0.0043 (5) |
C15 | 0.0297 (7) | 0.0246 (7) | 0.0247 (7) | −0.0080 (6) | −0.0082 (6) | −0.0042 (5) |
C16 | 0.0297 (8) | 0.0454 (9) | 0.0289 (8) | −0.0093 (7) | −0.0061 (6) | −0.0139 (7) |
C17 | 0.0337 (8) | 0.0429 (9) | 0.0492 (10) | 0.0049 (7) | −0.0182 (7) | −0.0290 (8) |
C18 | 0.0472 (9) | 0.0217 (7) | 0.0557 (10) | −0.0003 (7) | −0.0299 (8) | −0.0121 (7) |
C19 | 0.0406 (8) | 0.0224 (7) | 0.0341 (8) | −0.0122 (6) | −0.0180 (7) | −0.0009 (6) |
C20 | 0.0202 (6) | 0.0219 (6) | 0.0225 (6) | −0.0043 (5) | −0.0064 (5) | −0.0034 (5) |
C21 | 0.0224 (6) | 0.0222 (6) | 0.0207 (6) | −0.0065 (5) | −0.0073 (5) | −0.0042 (5) |
C22 | 0.0256 (7) | 0.0264 (7) | 0.0276 (7) | −0.0031 (6) | −0.0061 (6) | −0.0036 (6) |
C23 | 0.0378 (8) | 0.0240 (7) | 0.0338 (8) | −0.0063 (6) | −0.0127 (7) | 0.0031 (6) |
C24 | 0.0366 (8) | 0.0352 (8) | 0.0230 (7) | −0.0183 (6) | −0.0067 (6) | 0.0003 (6) |
C25 | 0.0266 (7) | 0.0367 (8) | 0.0237 (7) | −0.0104 (6) | −0.0033 (6) | −0.0090 (6) |
C26 | 0.0252 (7) | 0.0236 (7) | 0.0242 (7) | −0.0047 (5) | −0.0063 (5) | −0.0054 (5) |
Geometric parameters (Å, º) top
P1—O1 | 1.4578 (10) | C12—H12A | 0.9500 |
P1—O2 | 1.5916 (9) | C13—C14 | 1.5127 (18) |
P1—O3 | 1.5948 (10) | C13—H13A | 0.9900 |
P1—N1 | 1.6232 (11) | C13—H13B | 0.9900 |
O2—C1 | 1.4092 (15) | C14—C19 | 1.3893 (19) |
O3—C7 | 1.4096 (15) | C14—C15 | 1.3907 (19) |
N1—C13 | 1.4693 (17) | C15—C16 | 1.383 (2) |
N1—C20 | 1.4707 (17) | C15—H15A | 0.9500 |
C1—C2 | 1.378 (2) | C16—C17 | 1.388 (2) |
C1—C6 | 1.3826 (19) | C16—H16A | 0.9500 |
C2—C3 | 1.386 (2) | C17—C18 | 1.378 (3) |
C2—H2A | 0.9500 | C17—H17A | 0.9500 |
C3—C4 | 1.382 (2) | C18—C19 | 1.387 (2) |
C3—H3A | 0.9500 | C18—H18A | 0.9500 |
C4—C5 | 1.382 (2) | C19—H19A | 0.9500 |
C4—H4A | 0.9500 | C20—C21 | 1.5151 (18) |
C5—C6 | 1.3913 (19) | C20—H20A | 0.9900 |
C5—H5A | 0.9500 | C20—H20B | 0.9900 |
C6—H6A | 0.9500 | C21—C22 | 1.3881 (19) |
C7—C8 | 1.3760 (19) | C21—C26 | 1.3919 (18) |
C7—C12 | 1.3791 (19) | C22—C23 | 1.393 (2) |
C8—C9 | 1.3880 (19) | C22—H22A | 0.9500 |
C8—H8A | 0.9500 | C23—C24 | 1.381 (2) |
C9—C10 | 1.382 (2) | C23—H23A | 0.9500 |
C9—H9A | 0.9500 | C24—C25 | 1.384 (2) |
C10—C11 | 1.384 (2) | C24—H24A | 0.9500 |
C10—H10A | 0.9500 | C25—C26 | 1.384 (2) |
C11—C12 | 1.384 (2) | C25—H25A | 0.9500 |
C11—H11A | 0.9500 | C26—H26A | 0.9500 |
| | | |
O1—P1—O2 | 115.77 (5) | N1—C13—H13A | 108.8 |
O1—P1—O3 | 116.27 (5) | C14—C13—H13A | 108.8 |
O2—P1—O3 | 97.78 (5) | N1—C13—H13B | 108.8 |
O1—P1—N1 | 113.54 (6) | C14—C13—H13B | 108.8 |
O2—P1—N1 | 104.31 (5) | H13A—C13—H13B | 107.7 |
O3—P1—N1 | 107.44 (5) | C19—C14—C15 | 118.94 (13) |
C1—O2—P1 | 122.79 (8) | C19—C14—C13 | 120.19 (12) |
C7—O3—P1 | 119.73 (8) | C15—C14—C13 | 120.80 (12) |
C13—N1—C20 | 115.99 (10) | C16—C15—C14 | 120.52 (13) |
C13—N1—P1 | 121.10 (9) | C16—C15—H15A | 119.7 |
C20—N1—P1 | 122.88 (9) | C14—C15—H15A | 119.7 |
C2—C1—C6 | 121.90 (12) | C15—C16—C17 | 120.07 (15) |
C2—C1—O2 | 116.55 (12) | C15—C16—H16A | 120.0 |
C6—C1—O2 | 121.40 (12) | C17—C16—H16A | 120.0 |
C1—C2—C3 | 118.83 (13) | C18—C17—C16 | 119.78 (14) |
C1—C2—H2A | 120.6 | C18—C17—H17A | 120.1 |
C3—C2—H2A | 120.6 | C16—C17—H17A | 120.1 |
C4—C3—C2 | 120.38 (14) | C17—C18—C19 | 120.22 (14) |
C4—C3—H3A | 119.8 | C17—C18—H18A | 119.9 |
C2—C3—H3A | 119.8 | C19—C18—H18A | 119.9 |
C5—C4—C3 | 120.03 (13) | C18—C19—C14 | 120.47 (14) |
C5—C4—H4A | 120.0 | C18—C19—H19A | 119.8 |
C3—C4—H4A | 120.0 | C14—C19—H19A | 119.8 |
C4—C5—C6 | 120.37 (13) | N1—C20—C21 | 112.18 (10) |
C4—C5—H5A | 119.8 | N1—C20—H20A | 109.2 |
C6—C5—H5A | 119.8 | C21—C20—H20A | 109.2 |
C1—C6—C5 | 118.49 (13) | N1—C20—H20B | 109.2 |
C1—C6—H6A | 120.8 | C21—C20—H20B | 109.2 |
C5—C6—H6A | 120.8 | H20A—C20—H20B | 107.9 |
C8—C7—C12 | 122.33 (12) | C22—C21—C26 | 118.74 (12) |
C8—C7—O3 | 120.00 (12) | C22—C21—C20 | 120.71 (12) |
C12—C7—O3 | 117.59 (12) | C26—C21—C20 | 120.54 (11) |
C7—C8—C9 | 118.41 (13) | C21—C22—C23 | 120.54 (13) |
C7—C8—H8A | 120.8 | C21—C22—H22A | 119.7 |
C9—C8—H8A | 120.8 | C23—C22—H22A | 119.7 |
C10—C9—C8 | 120.28 (14) | C24—C23—C22 | 120.13 (13) |
C10—C9—H9A | 119.9 | C24—C23—H23A | 119.9 |
C8—C9—H9A | 119.9 | C22—C23—H23A | 119.9 |
C9—C10—C11 | 120.20 (14) | C23—C24—C25 | 119.63 (13) |
C9—C10—H10A | 119.9 | C23—C24—H24A | 120.2 |
C11—C10—H10A | 119.9 | C25—C24—H24A | 120.2 |
C12—C11—C10 | 120.16 (14) | C24—C25—C26 | 120.35 (13) |
C12—C11—H11A | 119.9 | C24—C25—H25A | 119.8 |
C10—C11—H11A | 119.9 | C26—C25—H25A | 119.8 |
C7—C12—C11 | 118.61 (13) | C25—C26—C21 | 120.60 (13) |
C7—C12—H12A | 120.7 | C25—C26—H26A | 119.7 |
C11—C12—H12A | 120.7 | C21—C26—H26A | 119.7 |
N1—C13—C14 | 113.73 (11) | | |
Hydrogen-bond geometry (Å, º) topCg1, Cg2 and Cg1 are the centroids of the
C1–C6, C14–C19 and C7–C12 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···CG1i | 0.95 | 3.50 | 3.9798 (13) | 114 |
C13—H13B···CG1ii | 0.99 | 3.49 | 4.2048 (13) | 131 |
C18—H18A···CG3ii | 0.95 | 3.22 | 3.8839 (15) | 128 |
C8—H8A···CG2iii | 0.95 | 3.41 | 3.7716 (14) | 106 |
C6—H6A···O1 | 0.95 | 2.51 | 3.1488 (17) | 125 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+1, −y, −z. |
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