Two single-enanti­omer amido­phospho­esters: a database study on the chirality of (O)₂P(O)(N)-based structures

The crystal structures of two single-enanti­omer amido­phospho­esters with an (O)₂P(O)(N) skeleton, i.e. diphenyl [(R)-(+)-α-methyl­benzyl­amido]­phosphate, (I), and diphenyl [(S)-(−)-α-methyl­benzyl­amido]­phosphate, (II), both C₂₀H₂₀NO₃P, are reported. In both structures, chiral one-dimensional hydro­gen-bonded architectures, along [010], are mediated by N—H...OP inter­actions. The statistically identical assemblies include the noncentrosymmetric graph-set motif C(4) and the compounds crystallize in the chiral space group P2₁. As a result of synergistic co-operation from C—H...O inter­actions, a two-dimensional superstructure is built including a noncentrosymmetric R₄⁴(22) hydrogen-bonded motif. A Cambridge Structural Database survey was performed on (O)₂P(O)(N)-based structures in order to review the frequency of space groups observed in this family of compounds; the hydrogen-bond motifs in structures with chiral space groups and the types of groups inducing chirality are discussed. The ^2,3J_X–P (X = H or C) coupling constants from the NMR spectra of (I) and (II) have been studied. In each compound, the two diastereotopic C₆H₅O groups are different, which is reflected in the different chemical shifts and some coupling constants.

Computing details

For both structures, data collection: Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014) MSCServDetCCD = {5.7.3.4}; cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: enCIFer (Allen, et al., 2004 for (I); enCIFer (Allen et al., 2004) for (II).

Diphenyl [R-(+)-α-methylbenzylamido]phosphate (I)

Crystal data

C20H20NO3P	F(000) = 372
Mr = 353.34	Dx = 1.294 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.3449 (2) Å	Cell parameters from 13845 reflections
b = 7.3527 (1) Å	θ = 3.4–29.7°
c = 11.8641 (3) Å	µ = 0.17 mm^−1
β = 113.623 (3)°	T = 120 K
V = 906.72 (4) Å^3	Block, colourless
Z = 2	0.15 × 0.05 × 0.05 mm

Data collection

AFC11 (Right): Eulerian 3 circle CCD diffractometer	3245 reflections with I > 2σ(I)
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW	Rint = 0.030
Profile data from ω–scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −13→13
Tmin = 0.838, Tmax = 1.000	k = −8→8
16344 measured reflections	l = −14→14
3322 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.024	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 0.1116P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.061	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.16 e Å^−3
3322 reflections	Δρmin = −0.23 e Å^−3
230 parameters	Absolute structure: Flack x determined using 1454 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: −0.01 (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.11163 (4)	0.55894 (6)	−0.04250 (4)	0.01891 (13)
C1	0.1895 (2)	0.1114 (3)	−0.17193 (19)	0.0317 (5)
H1A	0.117455	0.152536	−0.246310	0.048*
H1B	0.159520	0.017335	−0.131115	0.048*
H1C	0.257187	0.061177	−0.194363	0.048*
O1	−0.00245 (12)	0.5827 (2)	−0.01508 (12)	0.0260 (3)
O2	0.10993 (12)	0.66116 (18)	−0.16137 (12)	0.0241 (3)
C2	0.24293 (18)	0.2716 (3)	−0.08488 (18)	0.0223 (4)
H2	0.271072	0.367118	−0.128810	0.027*
C3	0.35910 (18)	0.2144 (3)	0.02894 (17)	0.0216 (4)
O3	0.23881 (13)	0.6593 (2)	0.04634 (12)	0.0260 (3)
N1	0.13912 (15)	0.3473 (2)	−0.05525 (15)	0.0218 (3)
H1N	0.0931 (19)	0.273 (3)	−0.0303 (19)	0.026*
C20	0.40284 (18)	0.5715 (3)	0.23925 (19)	0.0300 (4)
H20	0.448329	0.514285	0.196962	0.036*
C19	0.4539 (2)	0.5766 (3)	0.3664 (2)	0.0362 (5)
H19	0.534906	0.521430	0.412026	0.043*
C18	0.3878 (2)	0.6614 (3)	0.4276 (2)	0.0380 (5)
H18	0.424179	0.666399	0.514934	0.046*
C17	0.2687 (2)	0.7391 (3)	0.36157 (19)	0.0357 (5)
H17	0.222697	0.794866	0.403915	0.043*
C16	0.21607 (19)	0.7360 (3)	0.23391 (19)	0.0279 (4)
H16	0.135014	0.790819	0.188194	0.033*
C15	0.28415 (18)	0.6514 (3)	0.17465 (18)	0.0234 (4)
C4	0.34404 (18)	0.1152 (3)	0.12231 (17)	0.0242 (4)
H4	0.260152	0.083866	0.115315	0.029*
C5	0.45040 (17)	0.0619 (3)	0.22540 (17)	0.0273 (4)
H5	0.439074	−0.005717	0.288557	0.033*
C6	0.57350 (19)	0.1071 (3)	0.23656 (19)	0.0291 (5)
H6	0.646440	0.071780	0.307487	0.035*
C9	0.00849 (17)	0.6461 (3)	−0.27699 (17)	0.0233 (4)
C8	0.4828 (2)	0.2567 (3)	0.0399 (2)	0.0259 (4)
H8	0.494569	0.322097	−0.023856	0.031*
C7	0.58893 (19)	0.2043 (3)	0.1433 (2)	0.0294 (5)
H7	0.672907	0.235115	0.150359	0.035*
C10	−0.1041 (2)	0.7429 (3)	−0.3018 (2)	0.0320 (5)
H10	−0.115946	0.810978	−0.239135	0.038*
C11	−0.1992 (2)	0.7379 (4)	−0.4207 (2)	0.0387 (5)
H11	−0.277448	0.802145	−0.439333	0.046*
C13	−0.0678 (2)	0.5446 (4)	−0.48532 (18)	0.0348 (5)
H13	−0.055745	0.477124	−0.548126	0.042*
C14	0.02776 (18)	0.5472 (3)	−0.36707 (17)	0.0283 (4)
H14	0.105535	0.481742	−0.348321	0.034*
C12	−0.1809 (2)	0.6405 (4)	−0.5117 (2)	0.0374 (5)
H12	−0.246008	0.639184	−0.592845	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0163 (2)	0.0187 (2)	0.0236 (2)	−0.00115 (19)	0.00990 (17)	−0.0023 (2)
C1	0.0416 (11)	0.0266 (12)	0.0279 (10)	0.0053 (9)	0.0148 (9)	−0.0023 (8)
O1	0.0206 (6)	0.0257 (7)	0.0357 (7)	−0.0005 (6)	0.0155 (5)	−0.0062 (6)
O2	0.0207 (6)	0.0224 (7)	0.0285 (7)	−0.0016 (5)	0.0092 (6)	0.0030 (6)
C2	0.0247 (10)	0.0197 (9)	0.0292 (9)	0.0032 (7)	0.0177 (8)	0.0031 (8)
C3	0.0238 (9)	0.0156 (9)	0.0298 (10)	0.0000 (7)	0.0153 (8)	−0.0031 (7)
O3	0.0232 (7)	0.0296 (8)	0.0265 (7)	−0.0086 (6)	0.0114 (6)	−0.0062 (6)
N1	0.0201 (8)	0.0198 (8)	0.0313 (8)	0.0001 (7)	0.0165 (7)	0.0015 (7)
C20	0.0241 (9)	0.0242 (10)	0.0396 (10)	0.0005 (9)	0.0106 (8)	−0.0066 (10)
C19	0.0302 (10)	0.0275 (11)	0.0397 (11)	0.0009 (10)	0.0022 (9)	0.0029 (10)
C18	0.0427 (12)	0.0375 (13)	0.0275 (11)	−0.0070 (11)	0.0076 (10)	0.0014 (10)
C17	0.0382 (12)	0.0409 (13)	0.0314 (11)	−0.0042 (11)	0.0175 (10)	−0.0072 (10)
C16	0.0236 (10)	0.0283 (11)	0.0314 (10)	−0.0005 (9)	0.0104 (9)	−0.0046 (9)
C15	0.0223 (9)	0.0210 (9)	0.0261 (9)	−0.0048 (8)	0.0088 (8)	−0.0026 (8)
C4	0.0215 (9)	0.0233 (10)	0.0299 (10)	−0.0016 (7)	0.0127 (8)	−0.0012 (7)
C5	0.0281 (9)	0.0259 (9)	0.0285 (9)	−0.0005 (10)	0.0121 (8)	0.0000 (10)
C6	0.0231 (9)	0.0267 (11)	0.0333 (10)	0.0037 (8)	0.0070 (8)	−0.0048 (8)
C9	0.0209 (9)	0.0229 (9)	0.0259 (9)	−0.0009 (8)	0.0091 (8)	0.0044 (8)
C8	0.0280 (10)	0.0184 (9)	0.0393 (11)	0.0012 (8)	0.0219 (9)	−0.0007 (9)
C7	0.0205 (9)	0.0240 (10)	0.0474 (12)	−0.0014 (8)	0.0175 (9)	−0.0083 (9)
C10	0.0311 (11)	0.0323 (11)	0.0332 (11)	0.0075 (9)	0.0134 (9)	0.0012 (9)
C11	0.0266 (11)	0.0460 (14)	0.0388 (12)	0.0108 (10)	0.0082 (10)	0.0078 (11)
C13	0.0418 (11)	0.0379 (13)	0.0285 (10)	0.0024 (11)	0.0179 (9)	0.0023 (10)
C14	0.0285 (9)	0.0279 (10)	0.0326 (9)	0.0041 (9)	0.0166 (8)	0.0040 (10)
C12	0.0341 (11)	0.0474 (13)	0.0273 (10)	−0.0003 (10)	0.0085 (9)	0.0063 (10)

Geometric parameters (Å, º)

P1—O1	1.4658 (13)	C17—H17	0.9500
P1—O3	1.5871 (14)	C16—C15	1.383 (3)
P1—O2	1.5913 (14)	C16—H16	0.9500
P1—N1	1.6059 (17)	C4—C5	1.387 (3)
C1—C2	1.523 (3)	C4—H4	0.9500
C1—H1A	0.9800	C5—C6	1.389 (3)
C1—H1B	0.9800	C5—H5	0.9500
C1—H1C	0.9800	C6—C7	1.385 (3)
O2—C9	1.397 (2)	C6—H6	0.9500
C2—N1	1.467 (2)	C9—C14	1.381 (3)
C2—C3	1.520 (3)	C9—C10	1.386 (3)
C2—H2	1.0000	C8—C7	1.385 (3)
C3—C8	1.392 (3)	C8—H8	0.9500
C3—C4	1.393 (3)	C7—H7	0.9500
O3—C15	1.399 (2)	C10—C11	1.391 (3)
N1—H1N	0.883 (13)	C10—H10	0.9500
C20—C19	1.383 (3)	C11—C12	1.380 (3)
C20—C15	1.385 (3)	C11—H11	0.9500
C20—H20	0.9500	C13—C12	1.385 (3)
C19—C18	1.384 (3)	C13—C14	1.388 (3)
C19—H19	0.9500	C13—H13	0.9500
C18—C17	1.385 (3)	C14—H14	0.9500
C18—H18	0.9500	C12—H12	0.9500
C17—C16	1.388 (3)
O1—P1—O3	116.47 (8)	C15—C16—H16	120.7
O1—P1—O2	116.24 (8)	C17—C16—H16	120.7
O3—P1—O2	93.09 (7)	C16—C15—C20	121.77 (19)
O1—P1—N1	111.00 (8)	C16—C15—O3	119.84 (17)
O3—P1—N1	110.73 (8)	C20—C15—O3	118.15 (17)
O2—P1—N1	107.94 (8)	C5—C4—C3	120.58 (17)
C2—C1—H1A	109.5	C5—C4—H4	119.7
C2—C1—H1B	109.5	C3—C4—H4	119.7
H1A—C1—H1B	109.5	C4—C5—C6	120.17 (19)
C2—C1—H1C	109.5	C4—C5—H5	119.9
H1A—C1—H1C	109.5	C6—C5—H5	119.9
H1B—C1—H1C	109.5	C7—C6—C5	119.41 (19)
C9—O2—P1	123.04 (11)	C7—C6—H6	120.3
N1—C2—C3	112.69 (15)	C5—C6—H6	120.3
N1—C2—C1	108.45 (16)	C14—C9—C10	121.59 (18)
C3—C2—C1	110.84 (16)	C14—C9—O2	118.55 (16)
N1—C2—H2	108.2	C10—C9—O2	119.61 (18)
C3—C2—H2	108.2	C7—C8—C3	120.43 (18)
C1—C2—H2	108.2	C7—C8—H8	119.8
C8—C3—C4	118.89 (18)	C3—C8—H8	119.8
C8—C3—C2	120.26 (16)	C6—C7—C8	120.50 (18)
C4—C3—C2	120.82 (16)	C6—C7—H7	119.8
C15—O3—P1	122.91 (12)	C8—C7—H7	119.8
C2—N1—P1	126.51 (13)	C9—C10—C11	118.5 (2)
C2—N1—H1N	119.1 (16)	C9—C10—H10	120.8
P1—N1—H1N	113.7 (16)	C11—C10—H10	120.8
C19—C20—C15	118.8 (2)	C12—C11—C10	120.5 (2)
C19—C20—H20	120.6	C12—C11—H11	119.7
C15—C20—H20	120.6	C10—C11—H11	119.7
C20—C19—C18	120.4 (2)	C12—C13—C14	120.0 (2)
C20—C19—H19	119.8	C12—C13—H13	120.0
C18—C19—H19	119.8	C14—C13—H13	120.0
C19—C18—C17	120.0 (2)	C9—C14—C13	119.20 (19)
C19—C18—H18	120.0	C9—C14—H14	120.4
C17—C18—H18	120.0	C13—C14—H14	120.4
C18—C17—C16	120.4 (2)	C11—C12—C13	120.2 (2)
C18—C17—H17	119.8	C11—C12—H12	119.9
C16—C17—H17	119.8	C13—C12—H12	119.9
C15—C16—C17	118.59 (19)
O1—P1—O2—C9	−51.61 (17)	C19—C20—C15—O3	174.51 (19)
O3—P1—O2—C9	−173.24 (15)	P1—O3—C15—C16	−68.4 (2)
N1—P1—O2—C9	73.80 (16)	P1—O3—C15—C20	117.13 (18)
N1—C2—C3—C8	−136.12 (18)	C8—C3—C4—C5	0.9 (3)
C1—C2—C3—C8	102.1 (2)	C2—C3—C4—C5	179.40 (19)
N1—C2—C3—C4	45.4 (2)	C3—C4—C5—C6	0.0 (3)
C1—C2—C3—C4	−76.3 (2)	C4—C5—C6—C7	−0.6 (3)
O1—P1—O3—C15	47.65 (17)	P1—O2—C9—C14	−107.98 (18)
O2—P1—O3—C15	169.09 (15)	P1—O2—C9—C10	77.7 (2)
N1—P1—O3—C15	−80.41 (16)	C4—C3—C8—C7	−1.3 (3)
C3—C2—N1—P1	96.74 (19)	C2—C3—C8—C7	−179.78 (18)
C1—C2—N1—P1	−140.17 (16)	C5—C6—C7—C8	0.3 (3)
O1—P1—N1—C2	178.56 (15)	C3—C8—C7—C6	0.7 (3)
O3—P1—N1—C2	−50.46 (18)	C14—C9—C10—C11	0.4 (3)
O2—P1—N1—C2	50.09 (18)	O2—C9—C10—C11	174.5 (2)
C15—C20—C19—C18	−0.6 (4)	C9—C10—C11—C12	−0.7 (4)
C20—C19—C18—C17	1.2 (4)	C10—C9—C14—C13	0.0 (3)
C19—C18—C17—C16	−1.4 (4)	O2—C9—C14—C13	−174.23 (19)
C18—C17—C16—C15	1.0 (3)	C12—C13—C14—C9	0.0 (3)
C17—C16—C15—C20	−0.4 (3)	C10—C11—C12—C13	0.8 (4)
C17—C16—C15—O3	−174.65 (18)	C14—C13—C12—C11	−0.4 (4)
C19—C20—C15—C16	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.88 (1)	1.94 (1)	2.815 (2)	172 (2)
C7—H7···O2^ii	0.95	2.47	3.352 (2)	153

Symmetry codes: (i) −x, y−1/2, −z; (ii) −x+1, y−1/2, −z.

Diphenyl [(S)-(–)-α-methylbenzylamido]phosphate (II)

Crystal data

C20H20NO3P	F(000) = 372
Mr = 353.34	Dx = 1.293 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.3482 (3) Å	Cell parameters from 4360 reflections
b = 7.3589 (1) Å	θ = 2.8–29.5°
c = 11.8714 (3) Å	µ = 0.17 mm^−1
β = 113.686 (3)°	T = 120 K
V = 907.87 (4) Å^3	Plate, colourless
Z = 2	0.25 × 0.10 × 0.05 mm

Data collection

AFC11 (Right): Eulerian 3 circle CCD diffractometer	2858 reflections with I > 2σ(I)
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW	Rint = 0.015
Profile data from ω–scans	θmax = 25.3°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −13→13
Tmin = 0.984, Tmax = 1.000	k = −8→7
4992 measured reflections	l = −13→14
2908 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 0.0982P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.15 e Å^−3
2908 reflections	Δρmin = −0.21 e Å^−3
230 parameters	Absolute structure: Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.06 (4)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.61151 (4)	0.34236 (6)	0.45731 (4)	0.01737 (14)
O1	0.49727 (12)	0.3188 (2)	0.48478 (13)	0.0243 (3)
O2	0.60976 (12)	0.2403 (2)	0.33860 (13)	0.0224 (3)
O3	0.73884 (13)	0.2421 (2)	0.54638 (13)	0.0240 (3)
N1	0.63904 (16)	0.5539 (2)	0.44474 (16)	0.0199 (4)
H1N	0.595 (2)	0.623 (3)	0.4741 (19)	0.024*
C1	0.6890 (2)	0.7906 (3)	0.3279 (2)	0.0298 (5)
H1A	0.756472	0.840944	0.305358	0.045*
H1B	0.659169	0.884371	0.368949	0.045*
H1C	0.616759	0.749541	0.253623	0.045*
C2	0.74292 (18)	0.6298 (3)	0.41504 (18)	0.0201 (4)
H2	0.771108	0.534590	0.371076	0.024*
C3	0.85904 (18)	0.6872 (3)	0.52900 (18)	0.0198 (4)
C4	0.84402 (18)	0.7860 (3)	0.62217 (18)	0.0230 (5)
H4	0.760075	0.816972	0.615132	0.028*
C5	0.95043 (18)	0.8398 (4)	0.72542 (17)	0.0254 (4)
H5	0.939103	0.907449	0.788514	0.030*
C6	1.07343 (19)	0.7947 (3)	0.7364 (2)	0.0273 (5)
H6	1.146384	0.830360	0.807278	0.033*
C7	1.08915 (19)	0.6976 (3)	0.6435 (2)	0.0278 (5)
H7	1.173247	0.667091	0.650786	0.033*
C8	0.9830 (2)	0.6445 (3)	0.5398 (2)	0.0243 (4)
H8	0.994718	0.578894	0.476176	0.029*
C9	0.50822 (18)	0.2553 (3)	0.22246 (18)	0.0217 (4)
C10	0.3956 (2)	0.1584 (3)	0.1978 (2)	0.0293 (5)
H10	0.383639	0.090261	0.260369	0.035*
C11	0.3006 (2)	0.1641 (4)	0.0785 (2)	0.0371 (6)
H11	0.222231	0.100206	0.059562	0.045*
C12	0.3191 (2)	0.2613 (4)	−0.0121 (2)	0.0355 (5)
H12	0.253925	0.262478	−0.093213	0.043*
C13	0.4318 (2)	0.3573 (4)	0.01420 (19)	0.0332 (5)
H13	0.443778	0.424826	−0.048592	0.040*
C14	0.52784 (19)	0.3546 (4)	0.13299 (18)	0.0265 (4)
H14	0.605597	0.420236	0.152039	0.032*
C15	0.78428 (18)	0.2498 (3)	0.67477 (18)	0.0220 (4)
C16	0.71610 (19)	0.1657 (3)	0.73405 (19)	0.0263 (5)
H16	0.634913	0.111176	0.688400	0.032*
C17	0.7690 (2)	0.1628 (4)	0.8619 (2)	0.0340 (5)
H17	0.723324	0.106870	0.904333	0.041*
C18	0.8878 (2)	0.2410 (4)	0.9276 (2)	0.0364 (6)
H18	0.924031	0.236838	1.014889	0.044*
C19	0.9538 (2)	0.3251 (4)	0.8665 (2)	0.0342 (5)
H19	1.034847	0.380043	0.912110	0.041*
C20	0.90283 (18)	0.3298 (3)	0.7393 (2)	0.0283 (5)
H20	0.948318	0.386903	0.697044	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0150 (2)	0.0164 (3)	0.0219 (2)	0.00093 (19)	0.00863 (17)	0.0024 (2)
O1	0.0196 (6)	0.0233 (9)	0.0333 (7)	0.0004 (6)	0.0141 (5)	0.0063 (7)
O2	0.0197 (7)	0.0197 (8)	0.0263 (7)	0.0015 (6)	0.0078 (5)	−0.0032 (6)
O3	0.0220 (7)	0.0257 (9)	0.0247 (7)	0.0079 (6)	0.0099 (6)	0.0057 (7)
N1	0.0200 (8)	0.0155 (9)	0.0307 (9)	−0.0001 (7)	0.0168 (7)	−0.0013 (8)
C1	0.0390 (12)	0.0246 (13)	0.0266 (10)	−0.0057 (9)	0.0140 (9)	0.0016 (9)
C2	0.0227 (10)	0.0158 (11)	0.0281 (10)	−0.0028 (7)	0.0167 (8)	−0.0022 (9)
C3	0.0220 (9)	0.0131 (10)	0.0283 (10)	0.0000 (7)	0.0143 (8)	0.0029 (8)
C4	0.0204 (9)	0.0227 (12)	0.0281 (10)	0.0020 (7)	0.0119 (8)	0.0005 (9)
C5	0.0272 (9)	0.0224 (11)	0.0262 (9)	0.0000 (10)	0.0104 (8)	0.0000 (11)
C6	0.0224 (10)	0.0237 (13)	0.0319 (10)	−0.0030 (8)	0.0068 (8)	0.0052 (9)
C7	0.0191 (9)	0.0214 (12)	0.0460 (12)	0.0023 (8)	0.0164 (9)	0.0088 (10)
C8	0.0258 (10)	0.0159 (11)	0.0384 (11)	−0.0011 (8)	0.0205 (9)	0.0010 (10)
C9	0.0202 (9)	0.0196 (10)	0.0248 (9)	0.0003 (8)	0.0087 (8)	−0.0046 (9)
C10	0.0307 (11)	0.0270 (13)	0.0303 (11)	−0.0079 (9)	0.0123 (9)	−0.0024 (10)
C11	0.0255 (11)	0.0442 (16)	0.0365 (12)	−0.0111 (10)	0.0071 (9)	−0.0076 (12)
C12	0.0342 (12)	0.0440 (15)	0.0239 (10)	0.0003 (11)	0.0072 (9)	−0.0069 (11)
C13	0.0392 (12)	0.0359 (15)	0.0274 (10)	−0.0009 (11)	0.0165 (9)	−0.0004 (12)
C14	0.0279 (10)	0.0253 (12)	0.0299 (10)	−0.0052 (9)	0.0155 (8)	−0.0053 (11)
C15	0.0209 (9)	0.0194 (11)	0.0240 (9)	0.0049 (8)	0.0073 (8)	0.0033 (9)
C16	0.0217 (10)	0.0265 (12)	0.0295 (10)	0.0010 (9)	0.0089 (8)	0.0046 (10)
C17	0.0371 (12)	0.0384 (15)	0.0297 (11)	0.0047 (11)	0.0167 (10)	0.0060 (11)
C18	0.0400 (13)	0.0374 (15)	0.0253 (11)	0.0078 (11)	0.0063 (10)	−0.0022 (11)
C19	0.0289 (10)	0.0244 (12)	0.0381 (11)	−0.0009 (10)	0.0018 (8)	−0.0026 (11)
C20	0.0232 (9)	0.0220 (11)	0.0377 (11)	−0.0006 (9)	0.0101 (8)	0.0055 (11)

Geometric parameters (Å, º)

P1—O1	1.4685 (13)	C8—H8	0.9500
P1—O3	1.5883 (14)	C9—C14	1.379 (3)
P1—O2	1.5902 (14)	C9—C10	1.388 (3)
P1—N1	1.6065 (18)	C10—C11	1.394 (3)
O2—C9	1.402 (2)	C10—H10	0.9500
O3—C15	1.400 (2)	C11—C12	1.376 (4)
N1—C2	1.470 (2)	C11—H11	0.9500
N1—H1N	0.875 (12)	C12—C13	1.383 (4)
C1—C2	1.528 (3)	C12—H12	0.9500
C1—H1A	0.9800	C13—C14	1.393 (3)
C1—H1B	0.9800	C13—H13	0.9500
C1—H1C	0.9800	C14—H14	0.9500
C2—C3	1.521 (3)	C15—C16	1.384 (3)
C2—H2	1.0000	C15—C20	1.384 (3)
C3—C4	1.390 (3)	C16—C17	1.390 (3)
C3—C8	1.396 (3)	C16—H16	0.9500
C4—C5	1.389 (3)	C17—C18	1.382 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.389 (3)	C18—C19	1.381 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.384 (3)	C19—C20	1.383 (3)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.389 (3)	C20—H20	0.9500
C7—H7	0.9500
O1—P1—O3	116.45 (8)	C7—C8—H8	120.0
O1—P1—O2	116.30 (8)	C3—C8—H8	120.0
O3—P1—O2	93.13 (8)	C14—C9—C10	121.99 (19)
O1—P1—N1	110.92 (9)	C14—C9—O2	118.44 (17)
O3—P1—N1	110.68 (9)	C10—C9—O2	119.4 (2)
O2—P1—N1	108.01 (9)	C9—C10—C11	118.0 (2)
C9—O2—P1	123.17 (12)	C9—C10—H10	121.0
C15—O3—P1	123.00 (12)	C11—C10—H10	121.0
C2—N1—P1	126.53 (14)	C12—C11—C10	120.8 (2)
C2—N1—H1N	121.1 (17)	C12—C11—H11	119.6
P1—N1—H1N	111.1 (17)	C10—C11—H11	119.6
C2—C1—H1A	109.5	C11—C12—C13	120.4 (2)
C2—C1—H1B	109.5	C11—C12—H12	119.8
H1A—C1—H1B	109.5	C13—C12—H12	119.8
C2—C1—H1C	109.5	C12—C13—C14	119.8 (2)
H1A—C1—H1C	109.5	C12—C13—H13	120.1
H1B—C1—H1C	109.5	C14—C13—H13	120.1
N1—C2—C3	112.58 (15)	C9—C14—C13	119.0 (2)
N1—C2—C1	108.35 (17)	C9—C14—H14	120.5
C3—C2—C1	110.81 (18)	C13—C14—H14	120.5
N1—C2—H2	108.3	C16—C15—C20	121.78 (19)
C3—C2—H2	108.3	C16—C15—O3	119.93 (18)
C1—C2—H2	108.3	C20—C15—O3	118.08 (18)
C4—C3—C8	119.06 (18)	C15—C16—C17	118.5 (2)
C4—C3—C2	120.91 (17)	C15—C16—H16	120.7
C8—C3—C2	120.02 (18)	C17—C16—H16	120.7
C5—C4—C3	120.69 (18)	C18—C17—C16	120.3 (2)
C5—C4—H4	119.7	C18—C17—H17	119.8
C3—C4—H4	119.7	C16—C17—H17	119.8
C4—C5—C6	120.0 (2)	C19—C18—C17	120.1 (2)
C4—C5—H5	120.0	C19—C18—H18	119.9
C6—C5—H5	120.0	C17—C18—H18	119.9
C7—C6—C5	119.7 (2)	C18—C19—C20	120.5 (2)
C7—C6—H6	120.2	C18—C19—H19	119.8
C5—C6—H6	120.2	C20—C19—H19	119.8
C6—C7—C8	120.52 (19)	C19—C20—C15	118.7 (2)
C6—C7—H7	119.7	C19—C20—H20	120.6
C8—C7—H7	119.7	C15—C20—H20	120.6
C7—C8—C3	120.1 (2)
O1—P1—O2—C9	51.71 (18)	C2—C3—C8—C7	179.65 (19)
O3—P1—O2—C9	173.36 (16)	P1—O2—C9—C14	107.7 (2)
N1—P1—O2—C9	−73.71 (17)	P1—O2—C9—C10	−77.6 (2)
O1—P1—O3—C15	−47.47 (19)	C14—C9—C10—C11	−0.2 (4)
O2—P1—O3—C15	−169.00 (16)	O2—C9—C10—C11	−174.7 (2)
N1—P1—O3—C15	80.41 (17)	C9—C10—C11—C12	0.8 (4)
O1—P1—N1—C2	−178.52 (16)	C10—C11—C12—C13	−0.9 (4)
O3—P1—N1—C2	50.63 (19)	C11—C12—C13—C14	0.4 (4)
O2—P1—N1—C2	−49.98 (18)	C10—C9—C14—C13	−0.2 (3)
P1—N1—C2—C3	−96.9 (2)	O2—C9—C14—C13	174.3 (2)
P1—N1—C2—C1	140.17 (17)	C12—C13—C14—C9	0.1 (4)
N1—C2—C3—C4	−45.4 (3)	P1—O3—C15—C16	68.2 (3)
C1—C2—C3—C4	76.1 (2)	P1—O3—C15—C20	−117.05 (19)
N1—C2—C3—C8	136.07 (19)	C20—C15—C16—C17	0.1 (3)
C1—C2—C3—C8	−102.4 (2)	O3—C15—C16—C17	174.7 (2)
C8—C3—C4—C5	−0.8 (3)	C15—C16—C17—C18	−0.6 (4)
C2—C3—C4—C5	−179.3 (2)	C16—C17—C18—C19	1.0 (4)
C3—C4—C5—C6	−0.1 (3)	C17—C18—C19—C20	−0.9 (4)
C4—C5—C6—C7	0.6 (4)	C18—C19—C20—C15	0.4 (4)
C5—C6—C7—C8	−0.2 (3)	C16—C15—C20—C19	0.0 (4)
C6—C7—C8—C3	−0.6 (3)	O3—C15—C20—C19	−174.7 (2)
C4—C3—C8—C7	1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.88 (1)	1.96 (1)	2.816 (2)	167 (2)
C7—H7···O2^ii	0.95	2.47	3.352 (2)	154

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y+1/2, −z+1.