Diastereotopic groups in two new single-enanti­omer structures (R₂)P(O)[NH-(+)CH(C₂H₅)(C₆H₅)] (R = OC₆H₅ and C₆H₅)

Two new single-enanti­omer phospho­rus structures were studied. Their geometries, conformations and NMR features are discussed.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.102
• Data-to-parameter ratio = 14.0

Structure: II

• Single-crystal X-ray study
• T = 95 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.092
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Datablock: I

No errors found in this datablock




Datablock: II

No errors found in this datablock

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Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003), JANA2006 (Petricek et al., 2014); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003), MCE (Rohlicek & Husak, 2007).

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

Crystal data

C21H22NO3P	Dx = 1.325 Mg m^−3
Mr = 367.38	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121	Cell parameters from 19519 reflections
a = 5.4947 (1) Å	θ = 4–68°
b = 8.1503 (1) Å	µ = 1.49 mm^−1
c = 41.1096 (7) Å	T = 120 K
V = 1841.03 (5) Å^3	Blade, clear colourless
Z = 4	0.90 × 0.27 × 0.07 mm
F(000) = 776

Data collection

Oxford Diffraction Gemini diffractometer	3262 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 74.9°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2017)	h = −6→6
Tmin = 0.34, Tmax = 0.90	k = −9→9
34246 measured reflections	l = −49→48
3356 independent reflections

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 > 3σ(F)] = 0.037	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.03P)^2 + 3.0P] , where P = (max(Fo^2,0) + 2Fc^2)/3
wR(F) = 0.102	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.33 e Å^−3
3355 reflections	Δρmin = −0.38 e Å^−3
240 parameters	Absolute structure: Parsons wt al. (2013), 1324 Friedel pairs
4 restraints	Absolute structure parameter: 0.013 (9)
Primary atom site location: other

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. X-ray analyses of I and II were performed on two different diffractometers, both using mirror-collimated Cu-Kα radiation (λ = 1.5418 Å), and CCD detector Atlas S2. The 120 K data set was acquired on a Gemini diffractometer with a classical sealed X-ray tube, while the 95 K data set was obtained on a SuperNova diffractometer with a micro-focus sealed tube. The data reduction and absorption correction were made with CrysAlis PRO software (Rigaku, 2017). The structures were solved by charge flipping methods using SUPERFLIP (Palatinus & Chapuis, 2007) software and refined by full-matrix least-squares on F squared value using Crystals (Betteridge et al., 2003) and JANA2006 (Petricek et al., 2014) software programs. MCE (Rohlicek & Husak, 2007) software was used to visualize residual electron density maps.

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

	x	y	z	Uiso*/Ueq
P1	0.47169 (12)	0.71916 (8)	0.639453 (15)	0.0179
O2	0.4682 (3)	0.7590 (2)	0.60181 (4)	0.0229
C3	0.2732 (5)	0.8149 (3)	0.58334 (6)	0.0194
C4	0.0936 (5)	0.9153 (3)	0.59535 (7)	0.0218
C5	−0.0889 (5)	0.9701 (4)	0.57438 (7)	0.0264
C6	−0.0868 (6)	0.9248 (4)	0.54188 (7)	0.0274
C7	0.0950 (6)	0.8226 (4)	0.53038 (7)	0.0287
C8	0.2758 (5)	0.7663 (4)	0.55103 (6)	0.0244
O9	0.2348 (3)	0.6673 (2)	0.65240 (5)	0.0226
O10	0.5773 (4)	0.8880 (2)	0.65292 (4)	0.0221
C11	0.6063 (5)	0.9175 (3)	0.68651 (7)	0.0204
C12	0.8179 (5)	0.8689 (3)	0.70180 (7)	0.0232
C13	0.8488 (6)	0.9095 (4)	0.73416 (7)	0.0293
C14	0.6729 (6)	0.9975 (4)	0.75073 (7)	0.0323
C15	0.4628 (6)	1.0441 (4)	0.73500 (8)	0.0335
C16	0.4291 (6)	1.0050 (4)	0.70255 (7)	0.0284
N17	0.6906 (4)	0.5889 (3)	0.64476 (5)	0.0183
C18	0.6554 (5)	0.4134 (3)	0.63655 (7)	0.0190
C19	0.6338 (5)	0.3836 (3)	0.60013 (7)	0.0191
C20	0.8049 (6)	0.4457 (3)	0.57846 (7)	0.0236
C21	0.7840 (6)	0.4160 (4)	0.54532 (7)	0.0267
C22	0.5918 (6)	0.3231 (3)	0.53328 (7)	0.0265
C23	0.4216 (5)	0.2595 (4)	0.55459 (7)	0.0264
C24	0.4427 (5)	0.2905 (3)	0.58786 (6)	0.0230
C25	0.8638 (5)	0.3149 (3)	0.65162 (7)	0.0246
C26	0.8837 (6)	0.3359 (4)	0.68815 (7)	0.0306
H41	0.0953	0.9440	0.6176	0.0258*
H51	−0.2169	1.0378	0.5825	0.0333*
H61	−0.2126	0.9629	0.5284	0.0334*
H71	0.0971	0.7921	0.5081	0.0351*
H81	0.4006	0.6971	0.5432	0.0311*
H121	0.9407	0.8103	0.6910	0.0282*
H131	0.9901	0.8782	0.7449	0.0362*
H141	0.6962	1.0245	0.7732	0.0385*
H151	0.3406	1.1020	0.7466	0.0414*
H161	0.2869	1.0386	0.6919	0.0336*
H181	0.4995	0.3782	0.6465	0.0220*
H201	0.9339	0.5088	0.5863	0.0278*
H211	0.9021	0.4591	0.5309	0.0327*
H221	0.5809	0.3042	0.5105	0.0308*
H231	0.2889	0.1950	0.5464	0.0310*
H241	0.3217	0.2488	0.6018	0.0291*
H251	1.0183	0.3522	0.6420	0.0296*
H252	0.8302	0.1979	0.6470	0.0306*
H263	1.0151	0.2655	0.6967	0.0474*
H262	0.9199	0.4496	0.6934	0.0469*
H261	0.7302	0.3052	0.6981	0.0460*
H171	0.837 (3)	0.625 (2)	0.6445 (7)	0.0219 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0183 (3)	0.0169 (3)	0.0184 (3)	0.0003 (3)	0.0003 (3)	−0.0009 (3)
O2	0.0178 (9)	0.0304 (10)	0.0207 (9)	0.0051 (9)	0.0004 (8)	0.0012 (7)
C3	0.0166 (13)	0.0204 (14)	0.0212 (13)	0.0002 (11)	−0.0014 (10)	0.0027 (10)
C4	0.0241 (15)	0.0203 (13)	0.0209 (13)	−0.0005 (12)	0.0004 (12)	−0.0009 (11)
C5	0.0215 (15)	0.0214 (14)	0.0364 (16)	0.0047 (12)	0.0003 (13)	0.0024 (12)
C6	0.0241 (15)	0.0249 (15)	0.0331 (16)	−0.0028 (12)	−0.0096 (13)	0.0053 (12)
C7	0.0328 (17)	0.0320 (16)	0.0213 (14)	−0.0007 (13)	−0.0056 (12)	0.0009 (12)
C8	0.0246 (14)	0.0262 (15)	0.0224 (13)	0.0035 (12)	0.0018 (11)	0.0007 (11)
O9	0.0194 (10)	0.0225 (10)	0.0259 (9)	0.0001 (8)	0.0017 (8)	−0.0009 (8)
O10	0.0248 (10)	0.0183 (9)	0.0233 (9)	−0.0007 (8)	−0.0009 (8)	−0.0003 (8)
C11	0.0222 (14)	0.0154 (12)	0.0235 (13)	−0.0048 (11)	0.0023 (11)	−0.0024 (11)
C12	0.0244 (15)	0.0221 (14)	0.0232 (14)	−0.0012 (12)	0.0029 (12)	−0.0018 (11)
C13	0.0314 (16)	0.0315 (16)	0.0252 (15)	−0.0041 (14)	−0.0009 (13)	0.0024 (13)
C14	0.0430 (19)	0.0289 (16)	0.0251 (15)	−0.0109 (15)	0.0066 (14)	−0.0058 (13)
C15	0.0321 (17)	0.0298 (16)	0.0385 (17)	−0.0019 (14)	0.0098 (15)	−0.0117 (13)
C16	0.0239 (15)	0.0232 (14)	0.0380 (16)	0.0030 (13)	0.0011 (13)	−0.0046 (12)
N17	0.0173 (11)	0.0173 (11)	0.0204 (12)	−0.0029 (9)	−0.0010 (10)	−0.0020 (9)
C18	0.0209 (13)	0.0146 (12)	0.0215 (13)	−0.0010 (11)	0.0033 (11)	−0.0024 (11)
C19	0.0204 (13)	0.0138 (13)	0.0230 (13)	0.0030 (11)	0.0017 (11)	−0.0028 (10)
C20	0.0235 (15)	0.0211 (14)	0.0261 (14)	−0.0029 (12)	0.0015 (12)	−0.0018 (11)
C21	0.0282 (16)	0.0245 (15)	0.0275 (15)	0.0017 (13)	0.0069 (13)	0.0021 (12)
C22	0.0339 (17)	0.0265 (15)	0.0191 (13)	0.0081 (13)	−0.0017 (12)	−0.0018 (11)
C23	0.0232 (15)	0.0270 (15)	0.0288 (14)	0.0019 (12)	−0.0056 (12)	−0.0075 (12)
C24	0.0211 (13)	0.0225 (13)	0.0254 (13)	0.0020 (13)	0.0020 (11)	−0.0004 (12)
C25	0.0295 (15)	0.0183 (14)	0.0261 (14)	0.0034 (12)	−0.0001 (12)	0.0018 (11)
C26	0.0413 (18)	0.0226 (15)	0.0279 (15)	0.0024 (14)	−0.0047 (13)	0.0016 (12)

Geometric parameters (Å, º)

P1—O2	1.5814 (18)	C15—C16	1.384 (4)
P1—O9	1.469 (2)	C15—H151	0.948
P1—O10	1.5924 (19)	C16—H161	0.937
P1—N17	1.619 (2)	N17—C18	1.482 (3)
O2—C3	1.390 (3)	N17—H171	0.854 (17)
C3—C4	1.373 (4)	C18—C19	1.522 (4)
C3—C8	1.386 (4)	C18—C25	1.530 (4)
C4—C5	1.396 (4)	C18—H181	0.991
C4—H41	0.945	C19—C20	1.391 (4)
C5—C6	1.386 (4)	C19—C24	1.390 (4)
C5—H51	0.954	C20—C21	1.388 (4)
C6—C7	1.383 (4)	C20—H201	0.933
C6—H61	0.939	C21—C22	1.390 (4)
C7—C8	1.385 (4)	C21—H211	0.946
C7—H71	0.948	C22—C23	1.383 (4)
C8—H81	0.945	C22—H221	0.953
O10—C11	1.411 (3)	C23—C24	1.396 (4)
C11—C12	1.380 (4)	C23—H231	0.960
C11—C16	1.375 (4)	C24—H241	0.940
C12—C13	1.382 (4)	C25—C26	1.516 (4)
C12—H121	0.938	C25—H251	0.985
C13—C14	1.383 (5)	C25—H252	0.989
C13—H131	0.929	C26—H263	0.987
C14—C15	1.377 (5)	C26—H262	0.972
C14—H141	0.959	C26—H261	0.970
O2—P1—O9	113.77 (11)	C15—C16—H161	119.7
O2—P1—O10	99.62 (10)	C11—C16—H161	121.2
O9—P1—O10	116.45 (11)	P1—N17—C18	120.34 (18)
O2—P1—N17	106.00 (11)	P1—N17—H171	118.2 (12)
O9—P1—N17	114.90 (12)	C18—N17—H171	116.6 (12)
O10—P1—N17	104.43 (11)	N17—C18—C19	112.8 (2)
P1—O2—C3	127.68 (17)	N17—C18—C25	108.4 (2)
O2—C3—C4	123.5 (2)	C19—C18—C25	111.9 (2)
O2—C3—C8	114.9 (2)	N17—C18—H181	107.4
C4—C3—C8	121.5 (3)	C19—C18—H181	107.0
C3—C4—C5	119.0 (3)	C25—C18—H181	109.2
C3—C4—H41	119.3	C18—C19—C20	121.3 (2)
C5—C4—H41	121.7	C18—C19—C24	120.2 (2)
C4—C5—C6	120.3 (3)	C20—C19—C24	118.5 (3)
C4—C5—H51	120.0	C19—C20—C21	120.6 (3)
C6—C5—H51	119.7	C19—C20—H201	119.6
C5—C6—C7	119.7 (3)	C21—C20—H201	119.8
C5—C6—H61	118.4	C20—C21—C22	120.5 (3)
C7—C6—H61	121.9	C20—C21—H211	119.5
C6—C7—C8	120.5 (3)	C22—C21—H211	120.1
C6—C7—H71	119.7	C21—C22—C23	119.5 (3)
C8—C7—H71	119.7	C21—C22—H221	119.1
C3—C8—C7	119.0 (3)	C23—C22—H221	121.4
C3—C8—H81	120.3	C22—C23—C24	119.8 (3)
C7—C8—H81	120.7	C22—C23—H231	119.7
P1—O10—C11	121.91 (16)	C24—C23—H231	120.5
O10—C11—C12	119.5 (2)	C23—C24—C19	121.1 (3)
O10—C11—C16	118.5 (3)	C23—C24—H241	118.1
C12—C11—C16	121.8 (3)	C19—C24—H241	120.7
C11—C12—C13	118.2 (3)	C18—C25—C26	113.3 (2)
C11—C12—H121	122.5	C18—C25—H251	108.7
C13—C12—H121	119.3	C26—C25—H251	107.6
C12—C13—C14	120.9 (3)	C18—C25—H252	106.8
C12—C13—H131	119.6	C26—C25—H252	108.1
C14—C13—H131	119.5	H251—C25—H252	112.4
C13—C14—C15	119.8 (3)	C25—C26—H263	110.0
C13—C14—H141	120.0	C25—C26—H262	109.9
C15—C14—H141	120.1	H263—C26—H262	109.0
C14—C15—C16	120.1 (3)	C25—C26—H261	109.0
C14—C15—H151	119.7	H263—C26—H261	109.6
C16—C15—H151	120.2	H262—C26—H261	109.3
C15—C16—C11	119.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H121···O9^i	0.94	2.55	3.474 (4)	170
N17—H171···O9^i	0.85	2.24	3.074 (4)	166 (2)

Symmetry code: (i) x+1, y, z.

N-[(R)-(+)-α-Ethylbenzyl]-P,P-diphenylphosphinic amide (II)

Crystal data

C21H22NOP	Z = 2
Mr = 335.39	F(000) = 356
Triclinic, P1	Dx = 1.233 Mg m^−3
a = 9.0483 (7) Å	Cu Kα radiation, λ = 1.54180 Å
b = 10.5533 (8) Å	Cell parameters from 11237 reflections
c = 11.0036 (6) Å	θ = 4–74°
α = 70.065 (6)°	µ = 1.39 mm^−1
β = 86.368 (5)°	T = 95 K
γ = 66.571 (7)°	Needle, colorless
V = 903.15 (13) Å^3	0.62 × 0.09 × 0.07 mm

Data collection

Oxford Diffraction SuperNova diffractometer	6648 reflections with I > 2.0σ(I)
Focussing mirrors monochromator	Rint = 0.036
ω scans	θmax = 74.8°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2017)	h = −10→11
Tmin = 0.49, Tmax = 0.91	k = −13→13
15035 measured reflections	l = −13→13
6781 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.05P)^2 + 0.53P] , where P = (max(Fo^2,0) + 2Fc^2)/3
R[F > 3σ(F)] = 0.034	(Δ/σ)max = 0.001
wR(F) = 0.092	Δρmax = 0.49 e Å^−3
S = 0.97	Δρmin = −0.40 e Å^−3
6779 reflections	Extinction correction: Larson (1970), Equation 22
443 parameters	Extinction coefficient: 12 (2)
11 restraints	Absolute structure: Parsons et al. (2013), 3140 Friedel pairs
Primary atom site location: other	Absolute structure parameter: −0.013 (7)
Hydrogen site location: difference Fourier map

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.

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

	x	y	z	Uiso*/Ueq
P1	0.65963 (7)	0.68073 (7)	0.14489 (6)	0.0147
O2	0.68651 (18)	0.78920 (16)	0.18817 (15)	0.0192
N3	0.5062 (2)	0.7351 (2)	0.04120 (17)	0.0183
C4	0.4906 (3)	0.8436 (2)	−0.0895 (2)	0.0186
C5	0.4419 (3)	0.7964 (2)	−0.1908 (2)	0.0200
C6	0.3292 (3)	0.7336 (2)	−0.1687 (2)	0.0246
C7	0.2863 (3)	0.6919 (3)	−0.2628 (3)	0.0311
C8	0.3541 (3)	0.7134 (3)	−0.3805 (3)	0.0375
C9	0.4638 (3)	0.7781 (3)	−0.4047 (3)	0.0358
C10	0.5082 (3)	0.8189 (3)	−0.3100 (2)	0.0280
C11	0.3751 (3)	0.9980 (2)	−0.0941 (2)	0.0224
C12	0.3668 (3)	1.1186 (3)	−0.2214 (2)	0.0301
C13	0.6291 (3)	0.5395 (2)	0.2788 (2)	0.0171
C14	0.5864 (3)	0.4341 (2)	0.2599 (2)	0.0231
C15	0.5756 (3)	0.3206 (3)	0.3661 (3)	0.0283
C16	0.6061 (3)	0.3133 (3)	0.4908 (2)	0.0326
C17	0.6464 (3)	0.4184 (3)	0.5101 (2)	0.0339
C18	0.6596 (3)	0.5315 (3)	0.4045 (2)	0.0244
C19	0.8355 (3)	0.5873 (2)	0.0723 (2)	0.0163
C20	0.9871 (3)	0.5761 (2)	0.1080 (2)	0.0228
C21	1.1249 (3)	0.4987 (3)	0.0594 (3)	0.0291
C22	1.1132 (3)	0.4300 (3)	−0.0238 (3)	0.0370
C23	0.9630 (4)	0.4415 (3)	−0.0610 (3)	0.0366
C24	0.8248 (3)	0.5197 (3)	−0.0129 (2)	0.0266
P25	0.07166 (8)	0.86743 (7)	0.21332 (6)	0.0153
O26	0.19971 (18)	0.79311 (17)	0.13860 (15)	0.0191
N27	−0.1158 (2)	0.9595 (2)	0.14867 (17)	0.0186
C28	−0.1622 (3)	1.0887 (2)	0.0291 (2)	0.0190
C29	−0.1193 (3)	1.0513 (2)	−0.0942 (2)	0.0181
C30	−0.0560 (3)	1.1317 (3)	−0.1945 (2)	0.0246
C31	−0.0237 (3)	1.1016 (3)	−0.3093 (2)	0.0284
C32	−0.0532 (3)	0.9893 (3)	−0.3247 (2)	0.0273
C33	−0.1146 (3)	0.9065 (3)	−0.2249 (2)	0.0255
C34	−0.1478 (3)	0.9383 (2)	−0.1108 (2)	0.0217
C35	−0.3445 (3)	1.1792 (2)	0.0259 (2)	0.0236
C36	−0.4123 (3)	1.3159 (3)	−0.0958 (3)	0.0292
C37	0.0538 (3)	0.7326 (2)	0.3613 (2)	0.0170
C38	0.1730 (3)	0.5907 (2)	0.3955 (2)	0.0199
C39	0.1665 (3)	0.4812 (3)	0.5077 (2)	0.0262
C40	0.0416 (3)	0.5138 (3)	0.5867 (2)	0.0262
C41	−0.0766 (3)	0.6557 (3)	0.5537 (2)	0.0258
C42	−0.0719 (3)	0.7651 (2)	0.4412 (2)	0.0216
C43	0.1205 (3)	0.9967 (2)	0.2565 (2)	0.0189
C44	0.2809 (3)	0.9847 (2)	0.2533 (2)	0.0212
C45	0.3232 (3)	1.0805 (3)	0.2895 (2)	0.0264
C46	0.2078 (3)	1.1884 (3)	0.3291 (2)	0.0277
C47	0.0476 (3)	1.2019 (2)	0.3324 (2)	0.0243
C48	0.0055 (3)	1.1064 (2)	0.2959 (2)	0.0209
H41	0.5974	0.8444	−0.1091	0.0220*
H61	0.2795	0.7205	−0.0895	0.0305*
H71	0.2113	0.6464	−0.2449	0.0358*
H81	0.3236	0.6870	−0.4464	0.0453*
H91	0.5092	0.7947	−0.4848	0.0425*
H101	0.5834	0.8620	−0.3268	0.0343*
H111	0.2680	0.9967	−0.0769	0.0261*
H112	0.4090	1.0174	−0.0231	0.0257*
H121	0.2982	1.2149	−0.2168	0.0438*
H122	0.3213	1.1064	−0.2928	0.0436*
H123	0.4734	1.1161	−0.2430	0.0437*
H141	0.5650	0.4389	0.1758	0.0280*
H151	0.5505	0.2486	0.3538	0.0328*
H161	0.6024	0.2356	0.5624	0.0404*
H171	0.6628	0.4139	0.5962	0.0414*
H181	0.6884	0.6026	0.4173	0.0270*
H201	0.9926	0.6245	0.1670	0.0274*
H211	1.2268	0.4921	0.0852	0.0351*
H221	1.2068	0.3769	−0.0554	0.0433*
H231	0.9537	0.3961	−0.1187	0.0442*
H241	0.7251	0.5273	−0.0381	0.0319*
H281	−0.1033	1.1485	0.0335	0.0213*
H301	−0.0382	1.2104	−0.1855	0.0287*
H311	0.0176	1.1593	−0.3771	0.0337*
H321	−0.0304	0.9685	−0.4040	0.0327*
H331	−0.1283	0.8249	−0.2332	0.0317*
H341	−0.1856	0.8793	−0.0420	0.0267*
H352	−0.4011	1.1147	0.0318	0.0272*
H351	−0.3627	1.2111	0.1016	0.0271*
H362	−0.5227	1.3761	−0.0867	0.0432*
H361	−0.4124	1.2855	−0.1701	0.0425*
H363	−0.3466	1.3730	−0.1133	0.0432*
H381	0.2588	0.5680	0.3428	0.0238*
H391	0.2475	0.3849	0.5279	0.0309*
H401	0.0361	0.4387	0.6628	0.0323*
H411	−0.1604	0.6800	0.6071	0.0306*
H421	−0.1508	0.8603	0.4175	0.0247*
H441	0.3606	0.9101	0.2267	0.0238*
H451	0.4286	1.0731	0.2856	0.0318*
H461	0.2360	1.2529	0.3533	0.0341*
H471	−0.0304	1.2756	0.3581	0.0302*
H481	−0.1012	1.1142	0.2988	0.0256*
H271	−0.169 (2)	0.907 (2)	0.159 (2)	0.0223 (19)*
H31	0.417 (2)	0.746 (2)	0.0763 (17)	0.0229 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0160 (2)	0.0161 (2)	0.0131 (2)	−0.0080 (2)	0.00316 (19)	−0.00467 (19)
O2	0.0189 (7)	0.0201 (7)	0.0238 (8)	−0.0108 (6)	0.0052 (6)	−0.0110 (6)
N3	0.0187 (9)	0.0216 (9)	0.0146 (8)	−0.0111 (7)	0.0048 (7)	−0.0032 (7)
C4	0.0205 (11)	0.0233 (10)	0.0133 (10)	−0.0131 (9)	0.0033 (8)	−0.0029 (8)
C5	0.0182 (10)	0.0200 (10)	0.0175 (10)	−0.0056 (8)	−0.0008 (8)	−0.0034 (8)
C6	0.0256 (12)	0.0231 (11)	0.0242 (11)	−0.0097 (10)	−0.0016 (9)	−0.0064 (9)
C7	0.0285 (13)	0.0254 (12)	0.0378 (14)	−0.0069 (10)	−0.0096 (11)	−0.0114 (11)
C8	0.0388 (16)	0.0336 (14)	0.0335 (14)	−0.0003 (12)	−0.0143 (12)	−0.0176 (12)
C9	0.0352 (15)	0.0427 (15)	0.0233 (12)	−0.0044 (12)	−0.0001 (11)	−0.0170 (11)
C10	0.0258 (12)	0.0350 (13)	0.0194 (11)	−0.0093 (10)	0.0028 (9)	−0.0083 (10)
C11	0.0272 (12)	0.0213 (11)	0.0186 (11)	−0.0121 (9)	0.0014 (9)	−0.0040 (9)
C12	0.0397 (14)	0.0233 (12)	0.0225 (12)	−0.0141 (11)	−0.0003 (10)	0.0001 (10)
C13	0.0144 (10)	0.0177 (10)	0.0171 (10)	−0.0054 (8)	0.0031 (8)	−0.0051 (8)
C14	0.0205 (11)	0.0238 (11)	0.0248 (11)	−0.0097 (9)	0.0071 (9)	−0.0079 (9)
C15	0.0253 (12)	0.0183 (11)	0.0378 (14)	−0.0108 (9)	0.0103 (10)	−0.0042 (10)
C16	0.0266 (12)	0.0243 (12)	0.0279 (13)	−0.0050 (10)	0.0102 (10)	0.0060 (10)
C17	0.0347 (14)	0.0377 (14)	0.0159 (11)	−0.0096 (11)	0.0062 (10)	0.0002 (10)
C18	0.0272 (12)	0.0258 (11)	0.0187 (11)	−0.0090 (10)	0.0015 (9)	−0.0081 (9)
C19	0.0165 (10)	0.0156 (9)	0.0161 (10)	−0.0077 (8)	0.0061 (8)	−0.0042 (8)
C20	0.0228 (11)	0.0210 (11)	0.0228 (11)	−0.0086 (9)	0.0035 (9)	−0.0059 (9)
C21	0.0209 (12)	0.0276 (12)	0.0373 (14)	−0.0124 (10)	0.0089 (10)	−0.0073 (11)
C22	0.0331 (14)	0.0324 (14)	0.0502 (17)	−0.0149 (11)	0.0257 (13)	−0.0216 (13)
C23	0.0477 (17)	0.0424 (15)	0.0403 (15)	−0.0287 (13)	0.0258 (13)	−0.0298 (13)
C24	0.0326 (13)	0.0336 (13)	0.0270 (12)	−0.0223 (11)	0.0116 (10)	−0.0171 (10)
P25	0.0168 (3)	0.0172 (2)	0.0135 (2)	−0.0086 (2)	0.00278 (19)	−0.00540 (19)
O26	0.0208 (8)	0.0215 (7)	0.0173 (7)	−0.0112 (6)	0.0044 (6)	−0.0068 (6)
N27	0.0201 (9)	0.0207 (9)	0.0179 (9)	−0.0133 (8)	0.0021 (7)	−0.0043 (7)
C28	0.0222 (11)	0.0156 (10)	0.0183 (10)	−0.0091 (8)	−0.0003 (8)	−0.0026 (8)
C29	0.0162 (10)	0.0167 (9)	0.0192 (10)	−0.0068 (8)	−0.0006 (8)	−0.0030 (8)
C30	0.0288 (12)	0.0226 (11)	0.0233 (11)	−0.0142 (10)	0.0007 (10)	−0.0040 (9)
C31	0.0291 (12)	0.0342 (13)	0.0165 (10)	−0.0147 (11)	0.0007 (9)	0.0002 (9)
C32	0.0240 (12)	0.0327 (13)	0.0183 (11)	−0.0056 (10)	0.0000 (9)	−0.0073 (10)
C33	0.0259 (12)	0.0293 (12)	0.0250 (12)	−0.0125 (10)	0.0028 (10)	−0.0120 (10)
C34	0.0226 (11)	0.0250 (11)	0.0201 (11)	−0.0132 (9)	0.0042 (9)	−0.0069 (9)
C35	0.0237 (12)	0.0228 (11)	0.0259 (12)	−0.0096 (9)	0.0015 (9)	−0.0099 (9)
C36	0.0240 (12)	0.0218 (11)	0.0359 (14)	−0.0056 (10)	−0.0056 (10)	−0.0058 (10)
C37	0.0187 (10)	0.0215 (10)	0.0152 (9)	−0.0113 (8)	0.0000 (8)	−0.0075 (8)
C38	0.0201 (11)	0.0220 (11)	0.0181 (10)	−0.0091 (9)	0.0040 (8)	−0.0070 (9)
C39	0.0303 (13)	0.0199 (11)	0.0216 (11)	−0.0085 (10)	0.0028 (9)	−0.0012 (9)
C40	0.0331 (13)	0.0263 (12)	0.0170 (10)	−0.0155 (10)	0.0023 (10)	−0.0005 (9)
C41	0.0258 (12)	0.0318 (12)	0.0199 (11)	−0.0125 (10)	0.0078 (9)	−0.0087 (9)
C42	0.0230 (11)	0.0224 (11)	0.0200 (11)	−0.0096 (9)	0.0032 (9)	−0.0076 (9)
C43	0.0221 (11)	0.0182 (10)	0.0142 (9)	−0.0069 (8)	0.0026 (8)	−0.0047 (8)
C44	0.0200 (11)	0.0258 (11)	0.0198 (11)	−0.0115 (9)	0.0025 (9)	−0.0074 (9)
C45	0.0259 (12)	0.0289 (12)	0.0321 (13)	−0.0177 (10)	0.0013 (10)	−0.0117 (10)
C46	0.0379 (14)	0.0257 (12)	0.0261 (12)	−0.0186 (11)	−0.0003 (10)	−0.0093 (10)
C47	0.0296 (13)	0.0207 (11)	0.0238 (11)	−0.0089 (9)	0.0038 (9)	−0.0108 (9)
C48	0.0226 (11)	0.0220 (10)	0.0187 (10)	−0.0112 (9)	0.0035 (9)	−0.0055 (8)

Geometric parameters (Å, º)

P1—O2	1.4846 (15)	P25—O26	1.4933 (15)
P1—N3	1.6367 (19)	P25—N27	1.6426 (19)
P1—C13	1.802 (2)	P25—C37	1.808 (2)
P1—C19	1.808 (2)	P25—C43	1.797 (2)
N3—C4	1.474 (2)	N27—C28	1.469 (3)
N3—H31	0.856 (16)	N27—H271	0.841 (16)
C4—C5	1.517 (3)	C28—C29	1.524 (3)
C4—C11	1.532 (3)	C28—C35	1.538 (3)
C4—H41	0.980	C28—H281	0.988
C5—C6	1.391 (3)	C29—C30	1.391 (3)
C5—C10	1.391 (3)	C29—C34	1.386 (3)
C6—C7	1.383 (3)	C30—C31	1.391 (3)
C6—H61	0.948	C30—H301	0.944
C7—C8	1.383 (4)	C31—C32	1.378 (4)
C7—H71	0.953	C31—H311	0.951
C8—C9	1.380 (4)	C32—C33	1.390 (3)
C8—H81	0.950	C32—H321	0.961
C9—C10	1.389 (4)	C33—C34	1.392 (3)
C9—H91	0.940	C33—H331	0.952
C10—H101	0.936	C34—H341	0.945
C11—C12	1.520 (3)	C35—C36	1.527 (3)
C11—H111	0.980	C35—H352	0.986
C11—H112	0.967	C35—H351	0.982
C12—H121	0.975	C36—H362	0.968
C12—H122	0.977	C36—H361	0.975
C12—H123	0.971	C36—H363	0.972
C13—C14	1.393 (3)	C37—C38	1.390 (3)
C13—C18	1.395 (3)	C37—C42	1.397 (3)
C14—C15	1.390 (3)	C38—C39	1.391 (3)
C14—H141	0.938	C38—H381	0.941
C15—C16	1.387 (4)	C39—C40	1.387 (3)
C15—H151	0.928	C39—H391	0.945
C16—C17	1.379 (4)	C40—C41	1.387 (3)
C16—H161	0.934	C40—H401	0.952
C17—C18	1.392 (3)	C41—C42	1.387 (3)
C17—H171	0.949	C41—H411	0.937
C18—H181	0.940	C42—H421	0.929
C19—C20	1.399 (3)	C43—C44	1.406 (3)
C19—C24	1.387 (3)	C43—C48	1.392 (3)
C20—C21	1.383 (3)	C44—C45	1.389 (3)
C20—H201	0.967	C44—H441	0.950
C21—C22	1.379 (4)	C45—C46	1.382 (4)
C21—H211	0.951	C45—H451	0.925
C22—C23	1.391 (4)	C46—C47	1.398 (4)
C22—H221	0.933	C46—H461	0.932
C23—C24	1.384 (3)	C47—C48	1.388 (3)
C23—H231	0.942	C47—H471	0.933
C24—H241	0.925	C48—H481	0.935
O2—P1—N3	119.94 (9)	O26—P25—N27	119.61 (9)
O2—P1—C13	111.80 (9)	O26—P25—C37	109.99 (9)
N3—P1—C13	102.43 (10)	N27—P25—C37	102.69 (10)
O2—P1—C19	110.23 (9)	O26—P25—C43	110.87 (9)
N3—P1—C19	105.15 (10)	N27—P25—C43	104.84 (10)
C13—P1—C19	106.21 (9)	C37—P25—C43	108.07 (10)
P1—N3—C4	120.91 (14)	P25—N27—C28	122.16 (15)
P1—N3—H31	113.3 (12)	P25—N27—H271	114.1 (12)
C4—N3—H31	114.3 (12)	C28—N27—H271	115.3 (12)
N3—C4—C5	110.46 (17)	N27—C28—C29	114.02 (17)
N3—C4—C11	110.64 (17)	N27—C28—C35	107.53 (17)
C5—C4—C11	113.02 (18)	C29—C28—C35	111.51 (18)
N3—C4—H41	108.1	N27—C28—H281	108.1
C5—C4—H41	106.1	C29—C28—H281	106.9
C11—C4—H41	108.3	C35—C28—H281	108.7
C4—C5—C6	121.51 (19)	C28—C29—C30	121.5 (2)
C4—C5—C10	119.7 (2)	C28—C29—C34	120.35 (19)
C6—C5—C10	118.8 (2)	C30—C29—C34	118.2 (2)
C5—C6—C7	120.4 (2)	C29—C30—C31	121.3 (2)
C5—C6—H61	120.3	C29—C30—H301	119.1
C7—C6—H61	119.3	C31—C30—H301	119.5
C6—C7—C8	120.3 (3)	C30—C31—C32	119.9 (2)
C6—C7—H71	119.1	C30—C31—H311	119.8
C8—C7—H71	120.5	C32—C31—H311	120.3
C7—C8—C9	119.8 (2)	C31—C32—C33	119.6 (2)
C7—C8—H81	120.9	C31—C32—H321	119.7
C9—C8—H81	119.2	C33—C32—H321	120.7
C8—C9—C10	120.0 (2)	C32—C33—C34	120.1 (2)
C8—C9—H91	120.5	C32—C33—H331	119.6
C10—C9—H91	119.5	C34—C33—H331	120.2
C5—C10—C9	120.6 (3)	C33—C34—C29	120.9 (2)
C5—C10—H101	120.0	C33—C34—H341	119.7
C9—C10—H101	119.4	C29—C34—H341	119.3
C4—C11—C12	113.76 (19)	C28—C35—C36	113.74 (19)
C4—C11—H111	107.7	C28—C35—H352	108.0
C12—C11—H111	110.6	C36—C35—H352	109.3
C4—C11—H112	108.3	C28—C35—H351	107.8
C12—C11—H112	109.8	C36—C35—H351	108.2
H111—C11—H112	106.4	H352—C35—H351	109.8
C11—C12—H121	110.4	C35—C36—H362	110.1
C11—C12—H122	110.6	C35—C36—H361	109.1
H121—C12—H122	108.0	H362—C36—H361	108.1
C11—C12—H123	111.5	C35—C36—H363	111.5
H121—C12—H123	109.3	H362—C36—H363	110.1
H122—C12—H123	106.9	H361—C36—H363	107.8
P1—C13—C14	121.84 (17)	P25—C37—C38	117.22 (16)
P1—C13—C18	118.28 (17)	P25—C37—C42	123.28 (17)
C14—C13—C18	119.8 (2)	C38—C37—C42	119.5 (2)
C13—C14—C15	120.0 (2)	C37—C38—C39	120.3 (2)
C13—C14—H141	120.4	C37—C38—H381	120.1
C15—C14—H141	119.6	C39—C38—H381	119.6
C14—C15—C16	119.9 (2)	C38—C39—C40	120.0 (2)
C14—C15—H151	120.2	C38—C39—H391	118.8
C16—C15—H151	119.9	C40—C39—H391	121.2
C15—C16—C17	120.3 (2)	C39—C40—C41	119.9 (2)
C15—C16—H161	120.3	C39—C40—H401	120.1
C17—C16—H161	119.4	C41—C40—H401	120.1
C16—C17—C18	120.2 (2)	C40—C41—C42	120.4 (2)
C16—C17—H171	119.2	C40—C41—H411	120.9
C18—C17—H171	120.5	C42—C41—H411	118.7
C13—C18—C17	119.7 (2)	C37—C42—C41	119.9 (2)
C13—C18—H181	119.8	C37—C42—H421	118.8
C17—C18—H181	120.5	C41—C42—H421	121.3
P1—C19—C20	119.48 (17)	P25—C43—C44	118.93 (17)
P1—C19—C24	121.36 (18)	P25—C43—C48	122.26 (18)
C20—C19—C24	119.1 (2)	C44—C43—C48	118.8 (2)
C19—C20—C21	120.8 (2)	C43—C44—C45	120.2 (2)
C19—C20—H201	118.2	C43—C44—H441	119.6
C21—C20—H201	121.0	C45—C44—H441	120.1
C20—C21—C22	119.6 (2)	C44—C45—C46	120.3 (2)
C20—C21—H211	119.4	C44—C45—H451	119.7
C22—C21—H211	120.9	C46—C45—H451	120.0
C21—C22—C23	120.1 (2)	C45—C46—C47	120.1 (2)
C21—C22—H221	119.2	C45—C46—H461	120.4
C23—C22—H221	120.7	C47—C46—H461	119.5
C22—C23—C24	120.3 (2)	C46—C47—C48	119.6 (2)
C22—C23—H231	120.7	C46—C47—H471	120.0
C24—C23—H231	119.1	C48—C47—H471	120.4
C19—C24—C23	120.1 (2)	C43—C48—C47	121.0 (2)
C19—C24—H241	119.9	C43—C48—H481	119.0
C23—C24—H241	120.0	C47—C48—H481	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N27—H271···O2^i	0.84	2.08	2.923 (4)	176 (2)
N3—H31···O26	0.86	1.97	2.817 (4)	173 (2)

Symmetry code: (i) x−1, y, z.