Conformational flexibility in amido­phospho­esters: a CSD analysis com­pleted with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

The crystal structures of diphenyl (cyclo­heptyl­amido)­phosphate, C₁₉H₂₄NO₃P or (C₆H₅O)₂P(O)(NHC₇H₁₃), (I), and diphenyl (di­benzyl­amido)­phosphate, C₂₆H₂₄NO₃P or (C₆H₅O)₂P(O)[N(CH₂C₆H₅)₂], (II), are reported. The NHC₇H₁₃ 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 (C₆H₅CH₂)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 (T_m) at 109 and 81 °C for (I) and (II), respectively, which agree with the strengths of the inter­molecular contacts and the melting points.

Computing details

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)

Crystal data

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) Å^3	Prism, colourless
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection

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

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 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(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H232···O9^i	0.97	2.57	3.516 (8)	166 (1)
N17—H171···O9^i	0.86	2.08	2.901 (8)	159 (4)

Symmetry code: (i) x+1/2, −y+3/2, z.

Diphenyl (dibenzylamido)phosphate (II)

Crystal data

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) Å^3	0.25 × 0.20 × 0.20 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.4112P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Cg1, 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···CG1^i	0.95	3.50	3.9798 (13)	114
C13—H13B···CG1^ii	0.99	3.49	4.2048 (13)	131
C18—H18A···CG3^ii	0.95	3.22	3.8839 (15)	128
C8—H8A···CG2^iii	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.