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The crystal structures of two single-enanti­omer amido­phos­pho­esters with an (O)2P(O)(N) skeleton and one single-enanti­omer phos­pho­ric tri­amide with an (N)2P(O)(N) skeleton were studied. The com­pounds are diphenyl [(R)-(+)-α-4-di­methyl­benzyl­amido]­phosphate, (I), and diphenyl [(S)-(−)-α-4-di­methyl­benzyl­amido]­phosphate, (II), both C21H22NO3P, and N-(2,6-di­fluoro­benzo­yl)-N′,N′′-bis­[(R)-(+)-α-ethyl­benz­yl]phos­pho­ric tri­amide, C25H28F2N3O2P, (III). The asymmetric units contain two amido­phos­pho­ester mol­ecules for (I) and (II), and one phos­pho­ric tri­amide mol­ecule for (III). In the crystal structures of (I) and (II), mol­ecules are assembled in a similar one-dimensional chiral ribbon architecture, but with almost a mirror-image relationship with respect to each other through N—H...O(P) and C—H...O(P) hydro­gen bonds along [010]. In the crystal structure of (III), the chiral tape architecture along [100] is mediated by N—H...O(P) and N—H...O(C) hydro­gen bonds, and the tapes are connected into slabs by C—H...O inter­actions (along the ab plane). The differences/similarities of the two diastereotopic phen­oxy groups in (I)/(II) and the two chiral amine fragments in (III) were studied on the grounds of geometry, conformation and contribution to the crystal packing, as well as 1H and 13C signals in a solution NMR study.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621002047/fp3087sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621002047/fp3087Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621002047/fp3087IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621002047/fp3087IIIsup4.hkl
Contains datablock III

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621002047/fp3087sup5.pdf
Additional figures and tables

CCDC references: 2064320; 2064319; 2064318

Computing details top

For all structures, data collection: GEMINI (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (I); SIR92 (Altomare et al., 1994) for (II), (III). For all structures, program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Diphenyl [(S)-(-)-α-4-dimethylbenzylamido]phosphate (I) top
Crystal data top
C21H22NO3PF(000) = 776
Mr = 367.38Dx = 1.296 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 11.6763 (1) ÅCell parameters from 27082 reflections
b = 7.2768 (1) Åθ = 4–68°
c = 22.3075 (1) ŵ = 1.46 mm1
β = 96.6429 (6)°T = 120 K
V = 1882.66 (3) Å3Block, colourless
Z = 40.77 × 0.50 × 0.23 mm
Data collection top
Oxford Diffraction Gemini
diffractometer
6658 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.040
φ & ω scansθmax = 67.7°, θmin = 3.8°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
h = 1313
Tmin = 0.55, Tmax = 0.71k = 88
37170 measured reflectionsl = 2626
6767 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.07P)2 + 0.62P] ,
where P = (max(Fo2,0) + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.037(Δ/σ)max = 0.001
wR(F2) = 0.094Δρmax = 0.16 e Å3
S = 0.99Δρmin = 0.24 e Å3
6767 reflectionsExtinction correction: Larson (1970), Equation 22
479 parametersExtinction coefficient: 4.7 (5)
9 restraintsAbsolute structure: Parsons et al. (2013), 3063 Friedel Pairs
Primary atom site location: otherAbsolute structure parameter: 0.005 (5)
Hydrogen site location: difference Fourier map
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. The X-ray diffraction measurements were carried out at 120 K on a Xcalibur, Gemini ultra diffractometer using the Cu Kα radiation (λ = 1.54184 Å) from a fine-focus sealed X-ray tube with a graphite monochromator and CCD detector Atlas S2. The data were corrected for absorption using the CrysAlis PRO software. The structures were solved by the charge-flipping method by program Superflip (Palatinus & Chapuis, 2007) and refined by full matrix least squares on F2 with Crystals program (Betteridge et al., 2003).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.35645 (4)0.36800 (8)0.263727 (19)0.0182
O10.23522 (11)0.3562 (2)0.23778 (6)0.0240
O20.38873 (12)0.26149 (19)0.32613 (6)0.0242
C10.36181 (17)0.3214 (3)0.38201 (9)0.0235
C20.27620 (19)0.4478 (3)0.38935 (9)0.0282
C30.2574 (2)0.4979 (3)0.44756 (10)0.0348
C40.3230 (2)0.4211 (3)0.49727 (9)0.0371
C50.4062 (2)0.2922 (4)0.48892 (10)0.0363
C60.42627 (18)0.2408 (3)0.43115 (9)0.0292
O30.44647 (11)0.2549 (2)0.23033 (6)0.0227
C70.44610 (16)0.2508 (3)0.16727 (8)0.0202
C80.35976 (17)0.1576 (3)0.13176 (9)0.0248
C90.36807 (18)0.1426 (3)0.07036 (9)0.0290
C100.46005 (19)0.2196 (3)0.04525 (9)0.0298
C110.54447 (19)0.3136 (3)0.08172 (9)0.0289
C120.53840 (17)0.3289 (3)0.14345 (9)0.0258
N10.39639 (13)0.5782 (2)0.27308 (7)0.0203
C130.51295 (16)0.6428 (3)0.29524 (8)0.0209
C140.50335 (19)0.8054 (3)0.33747 (9)0.0304
C150.58089 (16)0.6928 (3)0.24337 (9)0.0199
C160.52780 (16)0.7826 (3)0.19243 (9)0.0229
C170.58858 (18)0.8192 (3)0.14405 (9)0.0258
C180.70361 (17)0.7682 (3)0.14501 (9)0.0252
C190.75803 (16)0.6860 (3)0.19736 (9)0.0235
C200.69675 (16)0.6482 (3)0.24568 (9)0.0226
C210.76752 (19)0.8001 (4)0.09124 (10)0.0382
P20.11485 (4)0.87341 (8)0.225528 (19)0.0179
O40.24107 (11)0.8664 (2)0.23428 (6)0.0232
O60.05091 (12)0.7741 (2)0.27593 (6)0.0240
C280.05292 (17)0.8443 (3)0.33446 (8)0.0221
C290.04660 (17)0.8187 (3)0.36153 (9)0.0266
C300.05006 (18)0.8808 (4)0.42002 (9)0.0316
C310.0439 (2)0.9702 (3)0.45047 (9)0.0316
C320.14252 (19)0.9949 (3)0.42253 (9)0.0313
C330.14817 (18)0.9307 (3)0.36428 (9)0.0271
O50.05543 (11)0.75067 (19)0.17150 (6)0.0222
C220.10223 (16)0.7485 (3)0.11609 (8)0.0216
C230.1819 (2)0.6154 (3)0.10656 (10)0.0310
C240.2232 (2)0.6080 (4)0.05062 (10)0.0371
C250.1827 (2)0.7300 (3)0.00529 (9)0.0334
C260.10249 (18)0.8615 (4)0.01565 (8)0.0297
C270.06197 (16)0.8733 (3)0.07171 (8)0.0251
N20.06771 (13)1.0800 (2)0.21615 (8)0.0212
C340.05409 (16)1.1347 (3)0.20458 (9)0.0227
C350.06374 (19)1.2933 (3)0.15932 (9)0.0306
C360.10619 (17)1.1896 (3)0.26143 (9)0.0211
C370.22077 (16)1.1487 (3)0.26727 (9)0.0234
C380.27116 (17)1.2065 (3)0.31741 (9)0.0248
C390.20789 (17)1.3066 (3)0.36353 (9)0.0243
C400.09269 (17)1.3444 (3)0.35766 (8)0.0250
C410.04268 (17)1.2883 (3)0.30748 (9)0.0245
C420.26229 (18)1.3750 (4)0.41733 (9)0.0337
H1c20.23290.49860.35480.0338*
H1c30.19800.58320.45270.0412*
H1c40.31130.45720.53670.0433*
H1c50.44910.23740.52260.0430*
H1c60.48170.15180.42490.0347*
H1c80.29800.10320.14960.0290*
H1c90.31040.07510.04600.0354*
H1c100.46730.20640.00390.0367*
H1c110.60730.36560.06460.0352*
H1c120.59590.39380.16850.0303*
H1c130.55200.53910.31790.0245*
H1c140.58100.84630.35390.0456*
H2c140.46020.76790.37060.0459*
H3c140.46500.91040.31650.0459*
H1c160.44980.81670.19090.0268*
H1c170.55180.88130.11030.0306*
H1c190.83730.65480.20010.0285*
H1c200.73470.58640.28000.0259*
H1c210.83650.72660.09430.0578*
H2c210.78890.92730.08890.0582*
H3c210.72090.77070.05490.0582*
H1c290.10950.75650.34060.0325*
H1c300.11830.86330.43880.0381*
H1c310.04001.01570.48970.0371*
H1c320.20791.05920.44340.0374*
H1c330.21420.94540.34550.0329*
H1c230.20790.53190.13660.0377*
H1c240.27890.52050.04360.0450*
H1c250.20810.72100.03330.0403*
H1c260.07690.94590.01430.0353*
H1c270.00820.96430.07950.0287*
H1c340.09651.02730.18680.0267*
H1c350.14551.32720.15030.0459*
H3c350.02071.39860.17670.0455*
H2c350.03391.25500.12200.0455*
H1c370.26531.07950.23640.0279*
H1c380.34961.17920.32090.0300*
H1c400.04861.41100.38850.0298*
H1c410.03551.31590.30410.0285*
H2c420.25061.50660.42350.0502*
H3c420.34471.35200.41210.0504*
H1c420.22951.31010.45340.0507*
H1n10.3449 (14)0.659 (2)0.2629 (10)0.0249 (19)*
H1n20.1201 (14)1.167 (2)0.2217 (10)0.0263 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0194 (2)0.0186 (2)0.0164 (2)0.0007 (2)0.00149 (16)0.0001 (2)
O10.0205 (6)0.0230 (7)0.0282 (7)0.0034 (6)0.0019 (5)0.0009 (6)
O20.0343 (8)0.0216 (7)0.0172 (6)0.0031 (6)0.0047 (5)0.0030 (5)
C10.0275 (10)0.0246 (11)0.0187 (9)0.0058 (8)0.0039 (7)0.0000 (7)
C20.0338 (11)0.0282 (11)0.0234 (10)0.0020 (9)0.0075 (8)0.0017 (8)
C30.0379 (12)0.0368 (12)0.0321 (12)0.0055 (10)0.0147 (10)0.0059 (10)
C40.0438 (13)0.0487 (15)0.0197 (10)0.0147 (11)0.0071 (9)0.0079 (9)
C50.0342 (11)0.0536 (15)0.0201 (10)0.0115 (11)0.0014 (8)0.0021 (10)
C60.0278 (11)0.0363 (12)0.0230 (10)0.0049 (9)0.0011 (8)0.0027 (9)
O30.0249 (7)0.0266 (7)0.0164 (6)0.0041 (6)0.0017 (5)0.0008 (6)
C70.0239 (9)0.0201 (9)0.0164 (9)0.0042 (8)0.0016 (7)0.0005 (7)
C80.0223 (9)0.0277 (10)0.0243 (10)0.0006 (8)0.0021 (8)0.0003 (8)
C90.0288 (10)0.0345 (12)0.0220 (10)0.0013 (9)0.0038 (8)0.0036 (9)
C100.0360 (12)0.0349 (12)0.0186 (9)0.0067 (9)0.0040 (8)0.0002 (9)
C110.0294 (10)0.0301 (11)0.0290 (10)0.0001 (8)0.0111 (8)0.0021 (8)
C120.0249 (10)0.0250 (11)0.0278 (10)0.0021 (8)0.0043 (8)0.0045 (8)
N10.0183 (8)0.0202 (8)0.0212 (8)0.0004 (7)0.0022 (6)0.0021 (7)
C130.0203 (9)0.0227 (10)0.0184 (9)0.0033 (8)0.0036 (7)0.0027 (8)
C140.0348 (11)0.0339 (12)0.0222 (10)0.0064 (9)0.0018 (8)0.0060 (9)
C150.0226 (9)0.0151 (9)0.0211 (9)0.0027 (7)0.0010 (7)0.0003 (7)
C160.0206 (9)0.0241 (10)0.0238 (10)0.0034 (8)0.0015 (7)0.0022 (8)
C170.0274 (10)0.0276 (11)0.0214 (9)0.0005 (8)0.0006 (8)0.0040 (8)
C180.0245 (10)0.0255 (11)0.0258 (10)0.0058 (9)0.0038 (8)0.0052 (8)
C190.0184 (9)0.0203 (10)0.0313 (11)0.0013 (8)0.0005 (8)0.0043 (8)
C200.0209 (9)0.0195 (10)0.0258 (10)0.0020 (8)0.0047 (8)0.0002 (8)
C210.0298 (11)0.0565 (16)0.0292 (11)0.0088 (11)0.0073 (9)0.0041 (10)
P20.0183 (2)0.0189 (2)0.0165 (2)0.0005 (2)0.00160 (15)0.0002 (2)
O40.0209 (6)0.0240 (7)0.0241 (6)0.0019 (6)0.0001 (5)0.0001 (6)
O60.0290 (7)0.0245 (7)0.0189 (7)0.0046 (6)0.0042 (5)0.0014 (6)
C280.0272 (9)0.0223 (10)0.0164 (8)0.0012 (8)0.0010 (7)0.0018 (8)
C290.0239 (9)0.0312 (12)0.0245 (10)0.0039 (8)0.0017 (8)0.0009 (8)
C300.0301 (10)0.0391 (12)0.0269 (10)0.0012 (10)0.0084 (8)0.0002 (11)
C310.0401 (12)0.0366 (12)0.0178 (9)0.0004 (10)0.0028 (9)0.0011 (9)
C320.0336 (12)0.0382 (12)0.0203 (10)0.0064 (10)0.0045 (8)0.0006 (9)
C330.0257 (10)0.0349 (12)0.0208 (9)0.0027 (9)0.0030 (8)0.0044 (8)
O50.0248 (7)0.0230 (7)0.0189 (6)0.0035 (6)0.0029 (5)0.0036 (6)
C220.0221 (9)0.0249 (10)0.0179 (9)0.0032 (8)0.0025 (7)0.0041 (8)
C230.0368 (12)0.0315 (11)0.0241 (10)0.0088 (10)0.0011 (9)0.0013 (9)
C240.0408 (13)0.0410 (14)0.0308 (11)0.0128 (11)0.0091 (10)0.0065 (10)
C250.0387 (12)0.0411 (13)0.0213 (10)0.0040 (10)0.0074 (9)0.0062 (9)
C260.0337 (10)0.0324 (11)0.0223 (9)0.0067 (11)0.0006 (8)0.0020 (9)
C270.0246 (9)0.0249 (9)0.0256 (9)0.0002 (9)0.0020 (7)0.0020 (9)
N20.0172 (8)0.0192 (8)0.0263 (8)0.0021 (7)0.0013 (6)0.0021 (7)
C340.0202 (9)0.0221 (10)0.0246 (10)0.0015 (8)0.0032 (7)0.0042 (8)
C350.0367 (12)0.0310 (11)0.0234 (10)0.0102 (10)0.0004 (9)0.0002 (9)
C360.0229 (9)0.0161 (9)0.0233 (9)0.0022 (7)0.0014 (7)0.0006 (8)
C370.0212 (9)0.0187 (9)0.0286 (10)0.0006 (8)0.0036 (8)0.0001 (8)
C380.0212 (10)0.0229 (10)0.0300 (10)0.0018 (8)0.0014 (8)0.0049 (8)
C390.0279 (10)0.0237 (10)0.0208 (9)0.0016 (8)0.0008 (8)0.0053 (8)
C400.0264 (10)0.0249 (11)0.0222 (9)0.0010 (8)0.0036 (7)0.0003 (8)
C410.0203 (9)0.0254 (10)0.0271 (10)0.0009 (8)0.0009 (8)0.0015 (8)
C420.0341 (11)0.0436 (12)0.0238 (9)0.0007 (11)0.0049 (8)0.0021 (11)
Geometric parameters (Å, º) top
P1—O11.4685 (13)P2—O41.4650 (13)
P1—O21.5997 (13)P2—O61.5930 (14)
P1—O31.5870 (14)P2—O51.5932 (13)
P1—N11.6056 (17)P2—N21.6063 (17)
O2—C11.390 (2)O6—C281.400 (2)
C1—C21.382 (3)C28—C291.383 (3)
C1—C61.386 (3)C28—C331.380 (3)
C2—C31.390 (3)C29—C301.386 (3)
C2—H1c20.947C29—H1c290.940
C3—C41.390 (3)C30—C311.384 (3)
C3—H1c30.948C30—H1c300.951
C4—C51.378 (4)C31—C321.383 (3)
C4—H1c40.943C31—H1c310.942
C5—C61.388 (3)C32—C331.389 (3)
C5—H1c50.941C32—H1c320.968
C6—H1c60.937C33—H1c330.926
O3—C71.406 (2)O5—C221.408 (2)
C7—C81.385 (3)C22—C231.377 (3)
C7—C121.378 (3)C22—C271.385 (3)
C8—C91.389 (3)C23—C241.390 (3)
C8—H1c80.949C23—H1c230.928
C9—C101.386 (3)C24—C251.387 (3)
C9—H1c90.952C24—H1c240.936
C10—C111.384 (3)C25—C261.377 (3)
C10—H1c100.941C25—H1c250.944
C11—C121.391 (3)C26—C271.390 (3)
C11—H1c110.945C26—H1c260.931
C12—H1c120.948C27—H1c270.943
N1—C131.470 (2)N2—C341.471 (2)
N1—H1n10.852 (16)N2—H1n20.878 (16)
C13—C141.525 (3)C34—C351.529 (3)
C13—C151.521 (3)C34—C361.522 (3)
C13—H1c130.990C34—H1c340.984
C14—H1c140.984C35—H1c350.984
C14—H2c140.980C35—H3c350.972
C14—H3c140.977C35—H2c350.979
C15—C161.393 (3)C36—C371.391 (3)
C15—C201.386 (3)C36—C411.395 (3)
C16—C171.384 (3)C37—C381.388 (3)
C16—H1c160.941C37—H1c370.957
C17—C181.391 (3)C38—C391.400 (3)
C17—H1c170.939C38—H1c380.949
C18—C191.398 (3)C39—C401.394 (3)
C18—C211.502 (3)C39—C421.506 (3)
C19—C201.388 (3)C40—C411.383 (3)
C19—H1c190.948C40—H1c400.944
C20—H1c200.951C41—H1c410.946
C21—H1c210.963C42—H2c420.975
C21—H2c210.962C42—H3c420.970
C21—H3c210.948C42—H1c420.972
O1—P1—O2115.72 (8)O4—P2—O6115.88 (8)
O1—P1—O3116.43 (8)O4—P2—O5115.13 (8)
O2—P1—O393.15 (7)O6—P2—O594.65 (7)
O1—P1—N1111.06 (8)O4—P2—N2111.98 (9)
O2—P1—N1108.23 (8)O6—P2—N2109.56 (8)
O3—P1—N1110.91 (8)O5—P2—N2108.27 (8)
P1—O2—C1124.99 (13)P2—O6—C28122.30 (13)
O2—C1—C2123.81 (18)O6—C28—C29115.71 (17)
O2—C1—C6114.72 (18)O6—C28—C33122.79 (17)
C2—C1—C6121.46 (19)C29—C28—C33121.49 (18)
C1—C2—C3118.7 (2)C28—C29—C30118.98 (19)
C1—C2—H1c2119.2C28—C29—H1c29119.8
C3—C2—H1c2122.1C30—C29—H1c29121.2
C2—C3—C4120.5 (2)C29—C30—C31120.50 (19)
C2—C3—H1c3118.8C29—C30—H1c30119.3
C4—C3—H1c3120.6C31—C30—H1c30120.2
C3—C4—C5119.8 (2)C30—C31—C32119.60 (19)
C3—C4—H1c4120.4C30—C31—H1c31120.0
C5—C4—H1c4119.7C32—C31—H1c31120.3
C4—C5—C6120.4 (2)C31—C32—C33120.7 (2)
C4—C5—H1c5119.9C31—C32—H1c32119.9
C6—C5—H1c5119.6C33—C32—H1c32119.4
C5—C6—C1119.1 (2)C32—C33—C28118.76 (19)
C5—C6—H1c6121.2C32—C33—H1c33121.1
C1—C6—H1c6119.8C28—C33—H1c33120.1
P1—O3—C7123.70 (12)P2—O5—C22119.41 (11)
O3—C7—C8120.00 (17)O5—C22—C23118.76 (18)
O3—C7—C12117.70 (17)O5—C22—C27119.08 (17)
C8—C7—C12122.09 (18)C23—C22—C27122.05 (18)
C7—C8—C9118.24 (18)C22—C23—C24118.5 (2)
C7—C8—H1c8120.2C22—C23—H1c23121.3
C9—C8—H1c8121.5C24—C23—H1c23120.2
C8—C9—C10120.86 (19)C23—C24—C25120.4 (2)
C8—C9—H1c9118.6C23—C24—H1c24119.8
C10—C9—H1c9120.5C25—C24—H1c24119.8
C9—C10—C11119.65 (19)C24—C25—C26120.23 (19)
C9—C10—H1c10121.1C24—C25—H1c25120.3
C11—C10—H1c10119.2C26—C25—H1c25119.5
C10—C11—C12120.45 (19)C25—C26—C27120.2 (2)
C10—C11—H1c11119.6C25—C26—H1c26120.4
C12—C11—H1c11119.9C27—C26—H1c26119.4
C11—C12—C7118.70 (18)C26—C27—C22118.7 (2)
C11—C12—H1c12120.6C26—C27—H1c27120.9
C7—C12—H1c12120.7C22—C27—H1c27120.5
P1—N1—C13126.30 (13)P2—N2—C34125.86 (14)
P1—N1—H1n1115.9 (11)P2—N2—H1n2115.6 (11)
C13—N1—H1n1117.8 (11)C34—N2—H1n2118.3 (11)
N1—C13—C14108.94 (16)N2—C34—C35108.42 (16)
N1—C13—C15111.39 (15)N2—C34—C36113.36 (15)
C14—C13—C15111.50 (16)C35—C34—C36110.23 (16)
N1—C13—H1c13106.3N2—C34—H1c34106.7
C14—C13—H1c13109.8C35—C34—H1c34109.8
C15—C13—H1c13108.8C36—C34—H1c34108.2
C13—C14—H1c14109.5C34—C35—H1c35108.7
C13—C14—H2c14109.3C34—C35—H3c35109.6
H1c14—C14—H2c14109.6H1c35—C35—H3c35109.2
C13—C14—H3c14112.0C34—C35—H2c35109.8
H1c14—C14—H3c14107.1H1c35—C35—H2c35109.2
H2c14—C14—H3c14109.3H3c35—C35—H2c35110.2
C13—C15—C16120.72 (17)C34—C36—C37120.23 (17)
C13—C15—C20120.55 (17)C34—C36—C41121.28 (18)
C16—C15—C20118.72 (18)C37—C36—C41118.43 (18)
C15—C16—C17120.43 (18)C36—C37—C38120.85 (18)
C15—C16—H1c16119.4C36—C37—H1c37119.5
C17—C16—H1c16120.2C38—C37—H1c37119.6
C16—C17—C18121.17 (18)C37—C38—C39120.87 (18)
C16—C17—H1c17119.4C37—C38—H1c38120.4
C18—C17—H1c17119.4C39—C38—H1c38118.7
C17—C18—C19118.15 (18)C38—C39—C40117.83 (18)
C17—C18—C21120.94 (19)C38—C39—C42121.49 (19)
C19—C18—C21120.90 (19)C40—C39—C42120.67 (18)
C18—C19—C20120.53 (18)C39—C40—C41121.34 (18)
C18—C19—H1c19120.1C39—C40—H1c40119.0
C20—C19—H1c19119.4C41—C40—H1c40119.7
C19—C20—C15120.87 (18)C36—C41—C40120.67 (18)
C19—C20—H1c20118.9C36—C41—H1c41119.1
C15—C20—H1c20120.1C40—C41—H1c41120.2
C18—C21—H1c21110.3C39—C42—H2c42111.9
C18—C21—H2c21110.3C39—C42—H3c42110.6
H1c21—C21—H2c21108.6H2c42—C42—H3c42107.9
C28—C21—H3c21111.1C39—C42—H1c42109.7
H1c21—C21—H3c21109.1H2c42—C42—H1c42108.9
H2c21—C21—H3c21107.4H3c42—C42—H1c42107.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H1c23···O10.932.583.477 (3)162 (1)
N1—H1n1···O40.851.992.841 (2)172 (2)
N2—H1n2···O1i0.881.932.807 (3)177 (2)
Symmetry code: (i) x, y+1, z.
Diphenyl [(S)-(-)-α-4-dimethylbenzylamido]phosphate (II) top
Crystal data top
C21H22NO3PDx = 1.296 Mg m3
Mr = 367.38Melting point: not measured K
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 11.6739 (1) ÅCell parameters from 15780 reflections
b = 7.2783 (1) Åθ = 4–68°
c = 22.3071 (2) ŵ = 1.46 mm1
β = 96.6380 (9)°T = 120 K
V = 1882.64 (4) Å3Needle, colourless
Z = 41.00 × 0.21 × 0.14 mm
F(000) = 776
Data collection top
Oxford Diffraction Gemini
diffractometer
6508 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 67.6°, θmin = 3.8°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
h = 1313
Tmin = 0.55, Tmax = 0.81k = 88
21509 measured reflectionsl = 2526
6650 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.16P)2 + 1.04P] ,
where P = (max(Fo2,0) + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.072(Δ/σ)max = 0.0002
wR(F2) = 0.182Δρmax = 0.32 e Å3
S = 0.98Δρmin = 0.30 e Å3
6650 reflectionsExtinction correction: Larson (1970), Equation 22
479 parametersExtinction coefficient: 3.6 (10)
9 restraintsAbsolute structure: Parsons et al. (2013), 2934 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.021 (7)
Hydrogen site location: difference Fourier map
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. The X-ray diffraction measurements were carried out at 120 K on a Xcalibur, Gemini ultra diffractometer using the Cu Kα radiation (λ = 1.54184 Å) from a fine-focus sealed X-ray tube with a graphite monochromator and CCD detector Atlas S2. The data were corrected for absorption using the CrysAlis PRO software. The structures were solved by the charge-flipping method by program Superflip (Palatinus & Chapuis, 2007) and refined by full matrix least squares on F2 with Crystals program (Betteridge et al., 2003).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3964 (2)0.0468 (4)0.27317 (12)0.0203
C130.5128 (3)0.0186 (5)0.29517 (14)0.0216
C140.5033 (3)0.1810 (5)0.33730 (16)0.0306
C150.5806 (3)0.0682 (4)0.24347 (15)0.0197
C200.6967 (3)0.0240 (5)0.24571 (15)0.0226
C190.7582 (3)0.0619 (5)0.19730 (16)0.0235
C180.7037 (3)0.1442 (5)0.14503 (16)0.0250
C170.5886 (3)0.1948 (5)0.14403 (15)0.0251
C160.5279 (3)0.1580 (5)0.19244 (15)0.0229
C210.7675 (3)0.1761 (7)0.09098 (17)0.0382
O30.4465 (2)0.3693 (4)0.23027 (10)0.0225
C70.4461 (3)0.3733 (5)0.16733 (14)0.0199
C120.5384 (3)0.2951 (5)0.14355 (16)0.0255
C110.5444 (3)0.3109 (5)0.08152 (16)0.0290
C100.4602 (3)0.4048 (6)0.04515 (15)0.0295
C90.3679 (3)0.4816 (6)0.07042 (15)0.0287
C80.3597 (3)0.4664 (5)0.13181 (15)0.0246
P10.35637 (6)0.25602 (14)0.26374 (3)0.0180
O10.23506 (19)0.2679 (4)0.23769 (10)0.0246
O20.3884 (2)0.3628 (3)0.32602 (10)0.0240
C10.3617 (3)0.3026 (5)0.38214 (14)0.0230
C60.4262 (3)0.3833 (6)0.43106 (16)0.0289
C50.4064 (4)0.3313 (7)0.48892 (16)0.0360
C30.2571 (4)0.1258 (6)0.44756 (17)0.0346
C20.2760 (3)0.1766 (5)0.38936 (16)0.0285
N20.0676 (2)0.5445 (4)0.21613 (13)0.0214
C340.0539 (3)0.4896 (5)0.20444 (15)0.0221
C350.0638 (3)0.3308 (5)0.15931 (16)0.0304
C360.1062 (3)0.4345 (5)0.26153 (15)0.0210
C410.0429 (3)0.3362 (5)0.30732 (16)0.0244
C400.0927 (3)0.2797 (5)0.35766 (15)0.0255
C390.2081 (3)0.3178 (5)0.36352 (15)0.0240
C380.2716 (3)0.4177 (5)0.31749 (16)0.0250
C370.2206 (3)0.4754 (5)0.26736 (15)0.0227
C420.2625 (3)0.2482 (7)0.41730 (15)0.0334
P20.11485 (6)0.75073 (14)0.22552 (3)0.0179
O40.24126 (19)0.7572 (4)0.23436 (10)0.0233
O50.05540 (19)0.8733 (3)0.17161 (10)0.0228
C220.1020 (3)0.8753 (5)0.11603 (14)0.0214
C270.0619 (3)0.7503 (6)0.07185 (14)0.0256
C260.1025 (3)0.7618 (6)0.01574 (14)0.0296
C250.1825 (3)0.8947 (6)0.00518 (16)0.0327
C240.2234 (4)1.0158 (6)0.05033 (17)0.0373
C230.1819 (3)1.0082 (6)0.10664 (16)0.0312
O60.0508 (2)0.8505 (3)0.27597 (10)0.0235
C280.0530 (3)0.7800 (5)0.33446 (14)0.0219
C330.1483 (3)0.6930 (5)0.36425 (15)0.0269
C320.1421 (3)0.6282 (6)0.42248 (16)0.0314
C310.0438 (4)0.6539 (6)0.45056 (16)0.0318
C300.0500 (3)0.7430 (6)0.42011 (15)0.0317
C290.0470 (3)0.8056 (5)0.36153 (16)0.0258
C40.3228 (4)0.2033 (6)0.49735 (16)0.0366
H1c130.55270.08260.31820.0225*
H1c140.57770.22490.35320.0440*
H3c140.46180.28100.31570.0439*
H2c140.46070.14480.36990.0440*
H1c200.73480.03560.27970.0238*
H1c190.83650.03090.19990.0250*
H1c170.55160.25870.11060.0279*
H1c160.45080.19340.19090.0249*
H3c210.71710.16360.05440.0543*
H2c210.79960.29920.09260.0543*
H1c210.82950.08750.09110.0542*
H1c120.59560.23030.16810.0279*
H1c110.60540.25600.06460.0331*
H1c100.46620.41940.00430.0332*
H1c90.31140.54680.04580.0320*
H1c80.29800.51970.14860.0269*
H1c60.48180.47330.42530.0318*
H1c50.44950.38640.52200.0422*
H1c30.19980.04240.45330.0379*
H1c20.23160.12550.35590.0309*
H1c340.09710.59520.18580.0236*
H1c350.14340.29520.15030.0420*
H2c350.03420.36910.12280.0423*
H3c350.01970.22580.17630.0418*
H1c410.03460.30820.30440.0260*
H1c400.04830.21140.38770.0289*
H1c380.34860.44610.32060.0278*
H1c370.26490.54330.23700.0249*
H3c420.34530.25490.41000.0461*
H2c420.24150.11950.42460.0460*
H1c420.23690.31870.45250.0462*
H1c270.00870.65910.07960.0269*
H1c260.07640.67590.01440.0331*
H1c250.20780.90670.03270.0371*
H1c240.27851.10180.04320.0418*
H1c230.20751.09220.13660.0339*
H1c330.21550.67630.34620.0300*
H1c320.20510.56660.44300.0340*
H1c310.04060.60950.48960.0350*
H1c300.11650.75850.43880.0351*
H1c290.11000.86670.34090.0290*
H1c40.31190.16330.53610.0401*
H1n20.1182 (17)0.457 (3)0.2231 (18)0.026 (2)*
H1n10.3456 (19)0.035 (3)0.2610 (17)0.024 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0168 (13)0.0203 (14)0.0234 (14)0.0001 (11)0.0004 (10)0.0020 (11)
C130.0206 (15)0.0238 (17)0.0192 (15)0.0027 (13)0.0030 (12)0.0027 (13)
C140.0330 (18)0.036 (2)0.0226 (16)0.0074 (15)0.0025 (14)0.0060 (15)
C150.0212 (16)0.0154 (15)0.0218 (15)0.0019 (12)0.0003 (12)0.0008 (12)
C200.0203 (16)0.0191 (16)0.0269 (16)0.0021 (13)0.0039 (13)0.0002 (14)
C190.0168 (14)0.0211 (17)0.0324 (18)0.0009 (13)0.0020 (13)0.0042 (14)
C180.0231 (16)0.0264 (18)0.0258 (17)0.0065 (14)0.0044 (13)0.0059 (14)
C170.0262 (17)0.0273 (19)0.0211 (15)0.0007 (13)0.0006 (13)0.0029 (13)
C160.0199 (15)0.0247 (17)0.0238 (16)0.0030 (14)0.0020 (12)0.0032 (13)
C210.0284 (18)0.058 (3)0.0293 (18)0.0075 (18)0.0081 (15)0.0037 (18)
O30.0239 (11)0.0273 (13)0.0163 (11)0.0048 (10)0.0021 (8)0.0006 (9)
C70.0228 (16)0.0211 (16)0.0162 (14)0.0035 (13)0.0035 (12)0.0001 (12)
C120.0242 (16)0.0257 (19)0.0272 (16)0.0022 (13)0.0047 (13)0.0049 (13)
C110.0303 (17)0.031 (2)0.0284 (17)0.0002 (14)0.0129 (14)0.0012 (14)
C100.0340 (19)0.036 (2)0.0193 (16)0.0060 (15)0.0051 (13)0.0006 (14)
C90.0291 (17)0.034 (2)0.0221 (16)0.0007 (15)0.0021 (13)0.0031 (15)
C80.0206 (15)0.0288 (18)0.0244 (16)0.0003 (14)0.0029 (12)0.0003 (14)
P10.0180 (4)0.0188 (4)0.0172 (4)0.0008 (3)0.0024 (3)0.0003 (3)
O10.0197 (11)0.0248 (12)0.0290 (11)0.0040 (10)0.0018 (8)0.0016 (10)
O20.0330 (13)0.0220 (12)0.0177 (11)0.0023 (10)0.0061 (9)0.0024 (9)
C10.0256 (16)0.0256 (18)0.0183 (14)0.0058 (13)0.0045 (12)0.0005 (12)
C60.0254 (18)0.036 (2)0.0255 (17)0.0044 (15)0.0017 (13)0.0028 (15)
C50.0332 (18)0.054 (3)0.0201 (16)0.0091 (19)0.0005 (14)0.0031 (17)
C30.036 (2)0.038 (2)0.0334 (19)0.0041 (17)0.0164 (16)0.0062 (17)
C20.0320 (19)0.0301 (19)0.0243 (17)0.0024 (15)0.0074 (14)0.0009 (14)
N20.0174 (13)0.0186 (14)0.0275 (14)0.0024 (11)0.0006 (10)0.0016 (11)
C340.0186 (15)0.0227 (17)0.0241 (16)0.0020 (13)0.0017 (12)0.0055 (13)
C350.0344 (19)0.0318 (19)0.0241 (17)0.0096 (16)0.0002 (14)0.0002 (15)
C360.0216 (16)0.0182 (16)0.0226 (15)0.0040 (13)0.0003 (12)0.0005 (13)
C410.0197 (15)0.0243 (17)0.0287 (17)0.0010 (13)0.0007 (13)0.0017 (14)
C400.0251 (16)0.0276 (19)0.0226 (15)0.0021 (14)0.0020 (12)0.0006 (14)
C390.0282 (17)0.0234 (17)0.0201 (15)0.0023 (13)0.0018 (13)0.0051 (13)
C380.0184 (16)0.0248 (18)0.0316 (18)0.0008 (13)0.0020 (13)0.0051 (14)
C370.0189 (15)0.0193 (16)0.0286 (17)0.0001 (13)0.0025 (13)0.0017 (14)
C420.0316 (18)0.045 (2)0.0245 (16)0.0009 (18)0.0062 (13)0.0012 (18)
P20.0171 (4)0.0189 (4)0.0177 (4)0.0002 (3)0.0024 (3)0.0002 (3)
O40.0203 (11)0.0251 (12)0.0243 (10)0.0022 (11)0.0013 (8)0.0008 (10)
O50.0247 (11)0.0243 (13)0.0201 (11)0.0035 (10)0.0057 (9)0.0040 (9)
C220.0213 (15)0.0257 (18)0.0174 (15)0.0038 (14)0.0024 (12)0.0024 (13)
C270.0260 (15)0.0247 (16)0.0261 (15)0.0004 (15)0.0034 (12)0.0020 (15)
C260.0324 (17)0.034 (2)0.0221 (15)0.0060 (18)0.0026 (13)0.0029 (16)
C250.037 (2)0.040 (2)0.0217 (16)0.0045 (16)0.0084 (14)0.0066 (15)
C240.041 (2)0.042 (2)0.0304 (19)0.0128 (18)0.0093 (16)0.0057 (16)
C230.037 (2)0.033 (2)0.0239 (17)0.0098 (16)0.0026 (14)0.0006 (15)
O60.0278 (12)0.0244 (13)0.0188 (11)0.0049 (10)0.0047 (9)0.0010 (9)
C280.0255 (16)0.0229 (17)0.0174 (14)0.0010 (13)0.0023 (12)0.0016 (13)
C330.0251 (17)0.033 (2)0.0223 (16)0.0028 (14)0.0034 (13)0.0040 (13)
C320.0327 (19)0.039 (2)0.0205 (16)0.0075 (16)0.0038 (14)0.0001 (15)
C310.041 (2)0.036 (2)0.0184 (16)0.0018 (17)0.0043 (14)0.0003 (15)
C300.0292 (17)0.040 (2)0.0275 (16)0.0004 (17)0.0095 (13)0.0007 (17)
C290.0229 (16)0.0291 (19)0.0251 (16)0.0037 (13)0.0018 (13)0.0011 (14)
C40.041 (2)0.050 (3)0.0200 (16)0.0150 (18)0.0082 (14)0.0072 (16)
Geometric parameters (Å, º) top
N1—C131.469 (4)N2—P21.604 (3)
N1—P11.600 (3)N2—H1n20.873 (18)
N1—H1n10.863 (18)C34—C351.528 (5)
C13—C141.522 (5)C34—C361.528 (5)
C13—C151.516 (4)C34—H1c340.984
C13—H1c130.984C35—H1c350.963
C14—H1c140.955C35—H2c350.961
C14—H3c140.971C35—H3c350.974
C14—H2c140.965C36—C411.388 (5)
C15—C201.388 (5)C36—C371.389 (5)
C15—C161.393 (5)C41—C401.385 (5)
C20—C191.392 (5)C41—H1c410.937
C20—H1c200.940C40—C391.396 (5)
C19—C181.397 (5)C40—H1c400.940
C19—H1c190.936C39—C381.399 (5)
C18—C171.390 (5)C39—C421.509 (5)
C18—C211.507 (5)C38—C371.391 (5)
C17—C161.384 (5)C38—H1c380.933
C17—H1c170.941C37—H1c370.943
C16—H1c160.934C42—H3c420.962
C21—H3c210.954C42—H2c420.977
C21—H2c210.971C42—H1c420.958
C21—H1c210.969P2—O41.467 (2)
O3—C71.404 (4)P2—O51.591 (2)
O3—P11.589 (2)P2—O61.596 (2)
C7—C121.378 (5)O5—C221.411 (4)
C7—C81.386 (5)C22—C271.382 (5)
C12—C111.398 (5)C22—C231.376 (5)
C12—H1c120.939C27—C261.391 (5)
C11—C101.381 (5)C27—H1c270.939
C11—H1c110.933C26—C251.383 (6)
C10—C91.389 (5)C26—H1c260.942
C10—H1c100.927C25—C241.381 (6)
C9—C81.388 (5)C25—H1c250.930
C9—H1c90.937C24—C231.399 (5)
C8—H1c80.934C24—H1c240.925
P1—O11.470 (2)C23—H1c230.930
P1—O21.598 (2)O6—C281.399 (4)
O2—C11.395 (4)C28—C331.382 (5)
C1—C61.383 (5)C28—C291.387 (5)
C1—C21.380 (5)C33—C321.392 (5)
C6—C51.390 (5)C33—H1c330.930
C6—H1c60.942C32—C311.383 (6)
C5—C41.377 (6)C32—H1c320.934
C5—H1c50.934C31—C301.381 (6)
C3—C21.392 (5)C31—H1c310.933
C3—C41.394 (6)C30—C291.388 (5)
C3—H1c30.923C30—H1c300.930
C2—H1c20.936C29—H1c290.934
N2—C341.468 (4)C4—H1c40.934
C13—N1—P1126.7 (2)N2—C34—C35108.7 (3)
C13—N1—H1n1117.1 (13)N2—C34—C36113.2 (3)
P1—N1—H1n1116.0 (13)C35—C34—C36110.1 (3)
N1—C13—C14109.1 (3)N2—C34—H1c34107.4
N1—C13—C15111.5 (3)C35—C34—H1c34108.5
C14—C13—C15111.5 (3)C36—C34—H1c34108.8
N1—C13—H1c13107.2C34—C35—H1c35109.8
C14—C13—H1c13108.9C34—C35—H2c35109.3
C15—C13—H1c13108.5H1c35—C35—H2c35109.5
C13—C14—H1c14111.2C34—C35—H3c35109.9
C13—C14—H3c14110.1H1c35—C35—H3c35108.9
H1c14—C14—H3c14108.3H2c35—C35—H3c35109.4
C13—C14—H2c14109.6C34—C36—C41121.2 (3)
H1c14—C14—H2c14109.7C34—C36—C37120.2 (3)
H3c14—C14—H2c14108.0C41—C36—C37118.5 (3)
C13—C15—C20120.7 (3)C36—C41—C40120.8 (3)
C13—C15—C16120.9 (3)C36—C41—H1c41119.8
C20—C15—C16118.4 (3)C40—C41—H1c41119.4
C15—C20—C19121.0 (3)C41—C40—C39121.1 (3)
C15—C20—H1c20120.3C41—C40—H1c40119.1
C19—C20—H1c20118.7C39—C40—H1c40119.8
C20—C19—C18120.4 (3)C40—C39—C38118.0 (3)
C20—C19—H1c19119.5C40—C39—C42120.5 (3)
C18—C19—H1c19120.1C38—C39—C42121.4 (3)
C19—C18—C17118.2 (3)C39—C38—C37120.5 (3)
C19—C18—C21120.9 (3)C39—C38—H1c38119.6
C17—C18—C21120.8 (3)C37—C38—H1c38120.0
C18—C17—C16121.1 (3)C38—C37—C36121.0 (3)
C18—C17—H1c17119.8C38—C37—H1c37119.0
C16—C17—H1c17119.0C36—C37—H1c37119.9
C15—C16—C17120.7 (3)C39—C42—H3c42110.8
C15—C16—H1c16119.5C39—C42—H2c42109.5
C17—C16—H1c16119.8H3c42—C42—H2c42107.8
C18—C21—H3c21110.9C39—C42—H1c42110.6
C18—C21—H2c21109.7H3c42—C42—H1c42108.9
H3c21—C21—H2c21108.5H2c42—C42—H1c42109.1
C18—C21—H1c21109.5N2—P2—O4111.88 (15)
H3c21—C21—H1c21109.0N2—P2—O5108.22 (14)
H2c21—C21—H1c21109.2O4—P2—O5115.33 (13)
C7—O3—P1123.7 (2)N2—P2—O6109.62 (14)
O3—C7—C12117.7 (3)O4—P2—O6115.90 (13)
O3—C7—C8120.0 (3)O5—P2—O694.52 (12)
C12—C7—C8122.1 (3)P2—O5—C22119.4 (2)
C7—C12—C11118.5 (3)O5—C22—C27119.1 (3)
C7—C12—H1c12121.1O5—C22—C23118.5 (3)
C11—C12—H1c12120.3C27—C22—C23122.2 (3)
C12—C11—C10120.6 (3)C22—C27—C26118.6 (3)
C12—C11—H1c11119.4C22—C27—H1c27120.7
C10—C11—H1c11120.0C26—C27—H1c27120.6
C11—C10—C9119.6 (3)C27—C26—C25120.2 (4)
C11—C10—H1c10120.3C27—C26—H1c26119.1
C9—C10—H1c10120.2C25—C26—H1c26120.8
C10—C9—C8120.9 (3)C26—C25—C24120.3 (3)
C10—C9—H1c9119.5C26—C25—H1c25120.8
C8—C9—H1c9119.5C24—C25—H1c25118.9
C9—C8—C7118.3 (3)C25—C24—C23120.3 (4)
C9—C8—H1c8120.4C25—C24—H1c24119.7
C7—C8—H1c8121.3C23—C24—H1c24120.0
N1—P1—O3110.88 (14)C24—C23—C22118.4 (4)
N1—P1—O1111.20 (14)C24—C23—H1c23120.3
O3—P1—O1116.33 (13)C22—C23—H1c23121.3
N1—P1—O2108.25 (14)P2—O6—C28122.1 (2)
O3—P1—O293.14 (13)O6—C28—C33122.9 (3)
O1—P1—O2115.68 (13)O6—C28—C29115.5 (3)
P1—O2—C1125.0 (2)C33—C28—C29121.6 (3)
O2—C1—C6114.6 (3)C28—C33—C32118.5 (3)
O2—C1—C2123.6 (3)C28—C33—H1c33121.5
C6—C1—C2121.7 (3)C32—C33—H1c33119.9
C1—C6—C5118.9 (4)C33—C32—C31120.9 (3)
C1—C6—H1c6120.6C33—C32—H1c32119.8
C5—C6—H1c6120.5C31—C32—H1c32119.4
C6—C5—C4120.5 (4)C32—C31—C30119.5 (3)
C6—C5—H1c5118.9C32—C31—H1c31120.0
C4—C5—H1c5120.5C30—C31—H1c31120.5
C2—C3—C4120.3 (4)C31—C30—C29120.8 (3)
C2—C3—H1c3119.9C31—C30—H1c30119.5
C4—C3—H1c3119.8C29—C30—H1c30119.7
C3—C2—C1118.7 (4)C30—C29—C28118.7 (3)
C3—C2—H1c2120.4C30—C29—H1c29121.0
C1—C2—H1c2120.9C28—C29—H1c29120.3
C34—N2—P2126.0 (2)C3—C4—C5119.9 (3)
C34—N2—H1n2116.9 (13)C3—C4—H1c4119.3
P2—N2—H1n2116.6 (13)C5—C4—H1c4120.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H1c23···O1i0.932.583.476 (5)162 (1)
N2—H1n2···O10.871.942.809 (4)178 (2)
N1—H1n1···O4ii0.861.992.848 (4)174 (2)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
N-(2,6-Difluorobenzoyl)-N',N''-bis[(R)-(+)-α-ethylbenzyl]phosphoric triamide (III) top
Crystal data top
C25H28F2N3O2PDx = 1.373 Mg m3
Mr = 471.49Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 24203 reflections
a = 4.9712 (1) Åθ = 4–68°
b = 20.1758 (2) ŵ = 1.45 mm1
c = 22.7451 (3) ÅT = 120 K
V = 2281.29 (6) Å3Blade, clear colourless
Z = 40.59 × 0.13 × 0.07 mm
F(000) = 992
Data collection top
Oxford Diffraction Gemini
diffractometer
3979 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.057
ω scansθmax = 67.7°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2017)
h = 55
Tmin = 0.50, Tmax = 0.90k = 2424
46145 measured reflectionsl = 2727
4088 independent reflections
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.04P)2 + 1.67P] ,
where P = (max(Fo2,0) + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max = 0.005
S = 0.92Δρmax = 0.19 e Å3
4088 reflectionsΔρmin = 0.32 e Å3
311 parametersAbsolute structure: Parsons et al. (2013), 1653 Friedel Pairs
12 restraintsAbsolute structure parameter: 0.007 (8)
Primary atom site location: structure-invariant direct methods
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. The X-ray diffraction measurements were carried out at 120 K on a Xcalibur, Gemini ultra diffractometer using the Cu Kα radiation (λ = 1.54184 Å) from a fine-focus sealed X-ray tube with a graphite monochromator and CCD detector Atlas S2. The data were corrected for absorption using the CrysAlis PRO software. The structures were solved by the charge-flipping method by program Superflip (Palatinus & Chapuis, 2007) and refined by full matrix least squares on F2 with Crystals program (Betteridge et al., 2003).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.07561 (10)0.66910 (2)0.73635 (2)0.0154
O20.1943 (3)0.64055 (6)0.74758 (6)0.0193
N30.0035 (3)0.74731 (8)0.71194 (8)0.0184
C40.1933 (4)0.79514 (9)0.70452 (8)0.0176
O50.4344 (3)0.78367 (7)0.70908 (6)0.0223
C60.0926 (4)0.86420 (9)0.69282 (8)0.0189
C70.1059 (4)0.87973 (10)0.65208 (9)0.0226
C80.1952 (5)0.94327 (11)0.64216 (10)0.0291
C90.0815 (5)0.99459 (10)0.67407 (10)0.0310
C100.1194 (5)0.98211 (10)0.71476 (10)0.0300
C110.2004 (5)0.91766 (10)0.72311 (9)0.0245
F120.3887 (3)0.90571 (6)0.76440 (6)0.0369
F130.2090 (3)0.83004 (6)0.61943 (5)0.0283
N140.2733 (3)0.67199 (8)0.79303 (7)0.0184
C150.1893 (4)0.69598 (10)0.85128 (8)0.0191
C160.3211 (4)0.65541 (10)0.90037 (9)0.0211
C170.5328 (4)0.61208 (10)0.89036 (9)0.0228
C180.6495 (5)0.57716 (11)0.93681 (10)0.0297
C190.5563 (6)0.58553 (12)0.99347 (9)0.0338
C200.3440 (6)0.62834 (13)1.00383 (10)0.0372
C210.2288 (5)0.66332 (11)0.95787 (9)0.0299
C220.2386 (4)0.77051 (10)0.85989 (9)0.0234
C230.5339 (5)0.78974 (10)0.85830 (10)0.0280
N240.2604 (3)0.63258 (8)0.68762 (7)0.0178
C250.1588 (4)0.61409 (10)0.62893 (8)0.0194
C260.3720 (4)0.62699 (10)0.58186 (8)0.0206
C270.5128 (4)0.68640 (10)0.58219 (9)0.0230
C280.6998 (5)0.70132 (11)0.53869 (9)0.0265
C290.7507 (5)0.65638 (11)0.49428 (9)0.0274
C300.6115 (5)0.59720 (11)0.49313 (9)0.0306
C310.4222 (5)0.58281 (10)0.53591 (9)0.0266
C320.0389 (4)0.54377 (10)0.62948 (9)0.0248
C330.2337 (5)0.48950 (10)0.64869 (10)0.0327
H810.32870.95030.61400.0359*
H910.13951.03940.66680.0376*
H1010.19911.01690.73670.0367*
H1510.00570.68730.85470.0227*
H1710.59540.60630.85180.0273*
H1810.79550.54910.93000.0370*
H1910.63700.56151.02470.0407*
H2010.27940.63441.04190.0438*
H2110.08580.69340.96620.0375*
H2220.16100.78420.89780.0284*
H2210.14730.79430.82940.0278*
H2330.54940.83730.86290.0422*
H2320.63110.76760.88930.0428*
H2310.61520.77720.82070.0417*
H2510.00630.64490.62190.0236*
H2710.47950.71700.61220.0283*
H2810.79280.74190.54020.0326*
H2910.88430.66640.46490.0346*
H3010.64270.56630.46310.0370*
H3110.32210.54260.53390.0318*
H3210.11560.54600.65670.0292*
H3220.03660.53220.59130.0302*
H3320.15150.44640.65010.0491*
H3310.29880.50030.68750.0479*
H3330.39060.48660.62210.0488*
H310.163 (3)0.7587 (8)0.7110 (10)0.0220 (19)*
H1410.439 (3)0.6737 (11)0.7864 (7)0.0229 (19)*
H2410.428 (3)0.6274 (11)0.6939 (7)0.0225 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0122 (2)0.0150 (2)0.0190 (2)0.00001 (19)0.00033 (19)0.00053 (18)
O20.0125 (6)0.0190 (6)0.0264 (7)0.0011 (5)0.0004 (5)0.0010 (5)
N30.0103 (8)0.0174 (8)0.0277 (8)0.0007 (6)0.0002 (6)0.0010 (7)
C40.0169 (10)0.0186 (9)0.0174 (9)0.0008 (8)0.0009 (8)0.0013 (7)
O50.0121 (7)0.0217 (7)0.0332 (7)0.0005 (6)0.0006 (6)0.0012 (6)
C60.0166 (9)0.0190 (9)0.0212 (9)0.0013 (8)0.0027 (8)0.0006 (7)
C70.0199 (10)0.0231 (10)0.0247 (10)0.0015 (8)0.0022 (8)0.0020 (8)
C80.0245 (11)0.0312 (11)0.0316 (11)0.0049 (9)0.0004 (10)0.0096 (9)
C90.0353 (13)0.0191 (10)0.0385 (12)0.0085 (10)0.0094 (11)0.0051 (9)
C100.0387 (14)0.0188 (10)0.0324 (11)0.0016 (9)0.0043 (10)0.0020 (8)
C110.0266 (11)0.0222 (10)0.0247 (10)0.0013 (9)0.0003 (9)0.0019 (8)
F120.0419 (8)0.0255 (6)0.0432 (7)0.0050 (6)0.0210 (7)0.0020 (5)
F130.0285 (6)0.0281 (6)0.0284 (6)0.0046 (6)0.0083 (5)0.0023 (5)
N140.0115 (8)0.0231 (8)0.0205 (8)0.0001 (7)0.0010 (6)0.0029 (7)
C150.0125 (9)0.0255 (10)0.0194 (9)0.0005 (8)0.0010 (8)0.0044 (8)
C160.0208 (10)0.0213 (10)0.0211 (10)0.0061 (8)0.0003 (8)0.0011 (7)
C170.0230 (11)0.0250 (10)0.0205 (10)0.0022 (8)0.0021 (8)0.0007 (8)
C180.0307 (13)0.0265 (11)0.0318 (11)0.0008 (9)0.0013 (9)0.0058 (9)
C190.0424 (15)0.0338 (12)0.0252 (11)0.0056 (11)0.0056 (11)0.0073 (9)
C200.0481 (17)0.0428 (14)0.0209 (11)0.0061 (12)0.0047 (10)0.0016 (9)
C210.0306 (12)0.0345 (11)0.0245 (10)0.0011 (10)0.0046 (9)0.0042 (9)
C220.0216 (11)0.0231 (10)0.0255 (10)0.0016 (9)0.0010 (9)0.0047 (8)
C230.0264 (12)0.0230 (10)0.0345 (11)0.0030 (9)0.0062 (10)0.0028 (9)
N240.0110 (8)0.0228 (8)0.0196 (8)0.0011 (7)0.0008 (6)0.0019 (6)
C250.0158 (10)0.0225 (10)0.0200 (9)0.0028 (8)0.0039 (8)0.0022 (7)
C260.0201 (11)0.0234 (10)0.0183 (9)0.0040 (8)0.0035 (8)0.0018 (7)
C270.0227 (11)0.0251 (10)0.0211 (10)0.0020 (8)0.0007 (8)0.0005 (8)
C280.0245 (11)0.0306 (11)0.0245 (10)0.0009 (9)0.0009 (9)0.0034 (8)
C290.0251 (12)0.0353 (12)0.0217 (10)0.0049 (9)0.0019 (9)0.0046 (8)
C300.0386 (14)0.0326 (12)0.0208 (10)0.0085 (10)0.0034 (10)0.0032 (8)
C310.0315 (12)0.0241 (10)0.0242 (10)0.0013 (10)0.0008 (10)0.0023 (8)
C320.0240 (11)0.0255 (11)0.0249 (10)0.0023 (9)0.0023 (9)0.0036 (8)
C330.0412 (14)0.0227 (11)0.0342 (12)0.0002 (10)0.0036 (11)0.0013 (9)
Geometric parameters (Å, º) top
P1—O21.4823 (14)C20—C211.385 (3)
P1—N31.7107 (16)C20—H2010.932
P1—N141.6221 (16)C21—H2110.954
P1—N241.6173 (16)C22—C231.519 (3)
N3—C41.360 (3)C22—H2220.984
N3—H310.861 (16)C22—H2210.958
C4—O51.225 (3)C23—H2330.969
C4—C61.504 (3)C23—H2320.965
C6—C71.389 (3)C23—H2310.979
C6—C111.387 (3)N24—C251.475 (2)
C7—C81.375 (3)N24—H2410.849 (16)
C7—F131.349 (2)C25—C261.529 (3)
C8—C91.385 (3)C25—C321.539 (3)
C8—H810.933C25—H2510.993
C9—C101.385 (3)C26—C271.388 (3)
C9—H910.962C26—C311.396 (3)
C10—C111.375 (3)C27—C281.390 (3)
C10—H1010.948C27—H2710.936
C11—F121.348 (3)C28—C291.381 (3)
N14—C151.471 (2)C28—H2810.940
N14—H1410.836 (16)C29—C301.380 (3)
C15—C161.532 (3)C29—H2910.963
C15—C221.536 (3)C30—C311.384 (3)
C15—H1510.988C30—H3010.936
C16—C171.387 (3)C31—H3110.953
C16—C211.395 (3)C32—C331.526 (3)
C17—C181.396 (3)C32—H3210.988
C17—H1710.938C32—H3220.974
C18—C191.380 (3)C33—H3320.962
C18—H1810.933C33—H3310.965
C19—C201.384 (4)C33—H3330.989
C19—H1910.948
O2—P1—N3102.99 (8)C16—C21—C20120.9 (2)
O2—P1—N14115.18 (8)C16—C21—H211120.3
N3—P1—N14110.60 (9)C20—C21—H211118.8
O2—P1—N24117.08 (8)C15—C22—C23113.66 (17)
N3—P1—N24108.47 (8)C15—C22—H222108.9
N14—P1—N24102.52 (8)C23—C22—H222109.2
P1—N3—C4123.32 (14)C15—C22—H221108.8
P1—N3—H31117.1 (11)C23—C22—H221108.2
C4—N3—H31118.4 (11)H222—C22—H221108.0
N3—C4—O5122.30 (18)C22—C23—H233109.1
N3—C4—C6116.62 (17)C22—C23—H232110.4
O5—C4—C6121.04 (17)H233—C23—H232109.8
C4—C6—C7124.28 (17)C22—C23—H231110.7
C4—C6—C11120.24 (18)H233—C23—H231108.6
C7—C6—C11115.48 (18)H232—C23—H231108.2
C6—C7—C8123.28 (19)P1—N24—C25122.74 (13)
C6—C7—F13118.01 (17)P1—N24—H241119.9 (11)
C8—C7—F13118.67 (19)C25—N24—H241117.0 (11)
C7—C8—C9118.6 (2)N24—C25—C26110.68 (15)
C7—C8—H81119.0N24—C25—C32111.00 (16)
C9—C8—H81122.4C26—C25—C32115.55 (16)
C8—C9—C10120.58 (19)N24—C25—H251104.4
C8—C9—H91119.3C26—C25—H251108.1
C10—C9—H91120.1C32—C25—H251106.4
C9—C10—C11118.4 (2)C25—C26—C27119.53 (17)
C9—C10—H101121.2C25—C26—C31122.65 (18)
C11—C10—H101120.4C27—C26—C31117.72 (19)
C6—C11—C10123.6 (2)C26—C27—C28121.35 (19)
C6—C11—F12118.37 (18)C26—C27—H271119.0
C10—C11—F12117.96 (19)C28—C27—H271119.7
P1—N14—C15123.74 (13)C27—C28—C29120.1 (2)
P1—N14—H141117.0 (11)C27—C28—H281119.4
C15—N14—H141115.3 (11)C29—C28—H281120.5
N14—C15—C16111.04 (16)C28—C29—C30119.3 (2)
N14—C15—C22113.06 (16)C28—C29—H291119.7
C16—C15—C22111.22 (16)C30—C29—H291120.9
N14—C15—H151107.0C29—C30—C31120.6 (2)
C16—C15—H151105.5C29—C30—H301120.4
C22—C15—H151108.6C31—C30—H301119.0
C15—C16—C17122.81 (17)C26—C31—C30120.9 (2)
C15—C16—C21118.77 (19)C26—C31—H311119.0
C17—C16—C21118.40 (19)C30—C31—H311120.0
C16—C17—C18120.60 (19)C25—C32—C33114.71 (18)
C16—C17—H171119.0C25—C32—H321105.3
C18—C17—H171120.4C33—C32—H321110.3
C17—C18—C19120.4 (2)C25—C32—H322111.3
C17—C18—H181120.3C33—C32—H322109.1
C19—C18—H181119.3H321—C32—H322105.7
C18—C19—C20119.4 (2)C32—C33—H332112.9
C18—C19—H191119.6C32—C33—H331108.2
C20—C19—H191120.9H332—C33—H331108.4
C19—C20—C21120.3 (2)C32—C33—H333111.6
C19—C20—H201120.2H332—C33—H333107.5
C21—C20—H201119.4H331—C33—H333108.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H101···O2i0.952.523.330 (3)144
C27—H271···O50.942.593.512 (3)168
N3—H31···O5ii0.862.062.923 (3)179 (2)
N14—H141···O2iii0.842.132.911 (3)154 (2)
N24—H241···O2iii0.852.263.039 (3)153 (1)
C28—H281···F13iii0.942.533.213 (2)130 (1)
C17—H171···O2iii0.942.683.566 (2)158 (1)
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x1, y, z; (iii) x+1, y, z.
 

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