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The crystal structures of N,N′-(cyclo­hexane-1,4-diyl)bis­(O,O′-di­phenyl­phosphor­amide), C30H32N2O6P2 or (C6H5O)2P(O)(1-NH)(C6H10)(4-NH)P(O)(OC6H5)2, (I), and N,N′-(1,4-phenyl­ene)bis­(O,O′-di­methyl­thio­phospho­ramide), C10H18N2O4P2S2 or (CH3O)2P(S)(1-NH)(C6H4)(4-NH)P(S)(OCH3)2, (II), have been investigated. In the structure of (I), with an (O)2(N)P(O) skeleton, two symmetry-independent phospho­ramide mol­ecules are linked through N—H...O=P hydrogen bonds. In the structure of (II), with an (O)2(N)P(S) skeleton, the ester O atoms take part in N—H...O—C hydrogen bonds as acceptors; the P=S groups do not participate in hydrogen-bonding inter­actions. The strengths of these hydrogen bonds were evaluated, using quantum chemical calculations with the GAUSSIAN09 software package at the B3LYP/6-311G(d,p) level of theory. For this, LP(O) to σ*(NH) charge transfers were studied, according to the second-order perturbation theory in natural bond orbital (NBO) methodology, for a three-component cluster of hydrogen-bonded mol­ecules for both structures, including all of the independent N—H...O hydrogen bonds observed in the crystal packing. The details of the inter­molecular inter­actions were studied by Hirshfeld surface maps and two-dimensional fingerprint plots.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618014006/cu3131sup1.cif
Contains datablocks bv91, bv18, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014006/cu3131bv91sup2.hkl
Contains datablock bv91

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014006/cu3131bv18sup3.hkl
Contains datablock bv18

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618014006/cu3131sup4.pdf
Additional details of the CSD analysis, Hirshfeld surface analysis, NMR spectra, delocalization energies, and natural charge and electron configuration

CCDC references: 1405616; 1871198

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2014) for bv91; COLLECT (Nonius, 1998) for bv18. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for bv91; DENZO SMN (Otwinowski & Minor, 1997) for bv18. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for bv91; DENZO SMN (Otwinowski & Minor, 1997) for bv18. Program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a) for bv91; SIR97 (Altomare et al., 1999) for bv18. Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) for bv91; SHELXL2015 (Sheldrick, 2015b) for bv18. Molecular graphics: ORTEPIII (Burnett & Johnson, 1996) for bv18. Software used to prepare material for publication: SHELXL2015 (Sheldrick, 2015b) for bv18.

N,N'-(Cyclohexane-1,4-diyl)bis(O,O'-diphenylphosphoramide) (bv91) top
Crystal data top
C30H32N2O6P2Z = 2
Mr = 578.51F(000) = 608
Triclinic, P1Dx = 1.338 Mg m3
a = 10.2789 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.8253 (4) ÅCell parameters from 12958 reflections
c = 15.0200 (6) Åθ = 3.2–29.8°
α = 101.229 (4)°µ = 0.20 mm1
β = 105.716 (4)°T = 120 K
γ = 109.782 (4)°Block, colourless
V = 1436.22 (12) Å30.20 × 0.20 × 0.10 mm
Data collection top
AFC11 (Right): Eulerian 3 circle CCD
diffractometer
9009 reflections with I > 2σ(I)
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kWRint = 0.023
Profile data from ω–scansθmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1112
Tmin = 0.893, Tmax = 1.000k = 1312
15732 measured reflectionsl = 1718
9396 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.2585P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max = 0.014
S = 1.01Δρmax = 0.40 e Å3
9396 reflectionsΔρmin = 0.30 e Å3
733 parametersAbsolute structure: Flack x determined using 3782 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
7 restraintsAbsolute structure parameter: 0.09 (3)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.01942 (7)0.09038 (7)0.06356 (5)0.01710 (15)
P20.09162 (7)0.54319 (7)0.53492 (5)0.01731 (16)
O10.1377 (2)0.0603 (2)0.10889 (15)0.0237 (4)
O20.0577 (2)0.5311 (2)0.48320 (15)0.0229 (4)
O30.0683 (2)0.07426 (19)0.04192 (14)0.0224 (4)
O40.1284 (2)0.25020 (19)0.02886 (14)0.0215 (4)
O50.2148 (2)0.69728 (19)0.58839 (14)0.0198 (4)
O60.1030 (2)0.4849 (2)0.62401 (15)0.0228 (4)
N10.0773 (3)0.0049 (2)0.13168 (18)0.0188 (5)
H1N0.161 (3)0.003 (3)0.107 (2)0.023*
N20.1578 (3)0.4690 (2)0.46732 (17)0.0196 (5)
H2N0.248 (3)0.481 (3)0.492 (2)0.024*
C10.0099 (3)0.0619 (3)0.0466 (2)0.0200 (6)
C20.0984 (3)0.1332 (3)0.0525 (2)0.0235 (6)
H2C0.1969010.0913460.0540630.028*
C30.0418 (4)0.2671 (3)0.0560 (2)0.0296 (7)
H3A0.1016580.3176390.0603580.036*
C40.1026 (4)0.3275 (3)0.0533 (2)0.0332 (7)
H4A0.1415770.4194960.0554560.040*
C50.1892 (4)0.2539 (4)0.0473 (3)0.0342 (8)
H5A0.2881790.2957870.0449000.041*
C60.1330 (3)0.1192 (3)0.0449 (2)0.0278 (7)
H6A0.1916720.0675460.0421180.033*
C70.1320 (3)0.3334 (3)0.0902 (2)0.0213 (6)
C80.2232 (3)0.4726 (3)0.0431 (2)0.0278 (7)
H8A0.2777010.5057120.0251220.033*
C90.2331 (4)0.5628 (3)0.0981 (3)0.0367 (8)
H9A0.2938770.6588550.0669750.044*
C100.1556 (4)0.5141 (4)0.1971 (3)0.0343 (8)
H10A0.1637780.5762780.2340620.041*
C110.0659 (4)0.3747 (3)0.2428 (2)0.0317 (7)
H11A0.0133640.3411870.3112470.038*
C120.0524 (3)0.2832 (3)0.1889 (2)0.0268 (6)
H12A0.0108520.1876840.2197740.032*
C130.2305 (3)0.7902 (3)0.5343 (2)0.0205 (6)
C140.1535 (3)0.8727 (3)0.5368 (2)0.0272 (6)
H14A0.0887630.8645000.5721820.033*
C150.1729 (4)0.9676 (3)0.4865 (3)0.0352 (8)
H15A0.1219141.0261390.4879070.042*
C160.2659 (4)0.9782 (3)0.4340 (3)0.0374 (8)
H16A0.2773871.0426760.3987680.045*
C170.3423 (4)0.8942 (3)0.4331 (3)0.0350 (8)
H17A0.4070970.9022040.3977340.042*
C180.3249 (3)0.7991 (3)0.4832 (2)0.0272 (7)
H18A0.3765890.7411530.4825680.033*
C190.0515 (3)0.5245 (3)0.6981 (2)0.0204 (6)
C200.0663 (3)0.4232 (3)0.7061 (2)0.0268 (6)
H20A0.1145560.3327940.6602400.032*
C210.1122 (4)0.4568 (4)0.7824 (2)0.0330 (7)
H21A0.1923780.3883760.7894290.040*
C220.0432 (4)0.5879 (4)0.8481 (2)0.0334 (7)
H22A0.0755350.6098280.9002810.040*
C230.0739 (4)0.6883 (4)0.8382 (2)0.0334 (8)
H23A0.1208620.7793040.8832140.040*
C240.1223 (3)0.6565 (3)0.7631 (2)0.0285 (7)
H24A0.2031240.7245890.7564410.034*
C260.0522 (3)0.0945 (3)0.2995 (2)0.0220 (6)
H26A0.1522660.0932730.2738950.026*
H26B0.0638670.0058090.3123370.026*
C270.0411 (3)0.2137 (3)0.3943 (2)0.0232 (6)
H27A0.0102220.2041820.4412900.028*
H27B0.1378740.2097690.4230430.028*
C280.0674 (3)0.3527 (3)0.3772 (2)0.0181 (6)
H28A0.0313680.3560250.3509780.022*
C290.1403 (3)0.3683 (3)0.3022 (2)0.0204 (6)
H29A0.2412390.3718070.3286860.024*
H29B0.1501830.4565950.2891100.024*
C300.0505 (3)0.2489 (3)0.2069 (2)0.0192 (6)
H30A0.1055900.2583150.1620670.023*
H30B0.0450860.2534960.1756470.023*
C320.0198 (3)0.1084 (3)0.2235 (2)0.0190 (6)
H32A0.1164080.1003910.2476020.023*
P510.59715 (8)0.51364 (7)0.56468 (5)0.02132 (17)
P520.49858 (7)0.01130 (7)0.03851 (5)0.02157 (17)
O510.4625 (2)0.5299 (2)0.51600 (15)0.0280 (5)
O520.6611 (2)0.0448 (2)0.07061 (15)0.0260 (5)
O530.7353 (2)0.6527 (2)0.63427 (15)0.0254 (5)
O540.5762 (2)0.4288 (2)0.63893 (15)0.0253 (5)
O550.4222 (2)0.0145 (2)0.05940 (16)0.0318 (5)
O560.4173 (2)0.1749 (2)0.00698 (16)0.0302 (5)
N510.6598 (3)0.4376 (3)0.49526 (19)0.0265 (6)
H51N0.754 (3)0.479 (3)0.508 (3)0.032*
N520.4371 (3)0.0499 (2)0.11513 (19)0.0219 (5)
H52N0.346 (3)0.017 (3)0.105 (3)0.026*
C510.7833 (3)0.7776 (3)0.6141 (2)0.0250 (6)
C520.7386 (4)0.7885 (4)0.5217 (3)0.0360 (8)
H52C0.6720850.7088350.4673070.043*
C530.7925 (5)0.9180 (4)0.5098 (3)0.0439 (9)
H53A0.7626470.9271190.4466430.053*
C540.8891 (5)1.0332 (4)0.5889 (3)0.0459 (9)
H54A0.9257271.1215610.5803530.055*
C550.9324 (5)1.0198 (4)0.6804 (3)0.0479 (10)
H55A0.9990181.0991970.7349690.057*
C560.8793 (4)0.8910 (3)0.6933 (3)0.0354 (8)
H56A0.9093420.8816470.7563310.043*
C570.5117 (3)0.4587 (3)0.7070 (2)0.0226 (6)
C580.5908 (3)0.5738 (3)0.7887 (2)0.0273 (7)
H58A0.6873270.6370500.7978580.033*
C590.5276 (4)0.5959 (3)0.8571 (2)0.0298 (7)
H59A0.5810000.6750470.9136080.036*
C600.3865 (4)0.5034 (3)0.8440 (2)0.0312 (7)
H60A0.3430890.5192390.8909880.037*
C610.3105 (4)0.3885 (3)0.7623 (3)0.0341 (7)
H61A0.2145240.3244950.7534760.041*
C620.3717 (3)0.3649 (3)0.6929 (2)0.0292 (7)
H62A0.3184410.2856180.6364430.035*
C630.4746 (3)0.0130 (3)0.1361 (2)0.0223 (6)
C640.5044 (4)0.0946 (3)0.1764 (3)0.0311 (7)
H64A0.4899260.1705910.1516480.037*
C650.5556 (4)0.0936 (4)0.2529 (3)0.0393 (8)
H65A0.5784120.1669970.2796900.047*
C660.5725 (4)0.0155 (4)0.2890 (3)0.0416 (9)
H66A0.6065020.0163850.3418210.050*
C670.5414 (4)0.1240 (4)0.2507 (3)0.0396 (8)
H67A0.5534880.1983390.2770990.048*
C680.4919 (4)0.1234 (4)0.1726 (3)0.0366 (8)
H68A0.4705420.1974400.1450230.044*
C690.4200 (4)0.2400 (3)0.0792 (3)0.0303 (7)
C700.5416 (4)0.2626 (4)0.1231 (3)0.0459 (10)
H70A0.6266650.2327960.1057120.055*
C710.5393 (5)0.3287 (5)0.1924 (4)0.0706 (16)
H71A0.6224470.3459670.2225930.085*
C720.4148 (5)0.3702 (6)0.2184 (5)0.0759 (17)
H72A0.4143840.4132250.2678000.091*
C730.2929 (5)0.3492 (4)0.1727 (4)0.0550 (12)
H73A0.2071700.3799740.1892580.066*
C740.2945 (4)0.2836 (3)0.1030 (3)0.0365 (8)
H74A0.2104610.2683580.0715140.044*
C750.5652 (3)0.3272 (3)0.4023 (2)0.0217 (6)
H75A0.4615880.2879690.4015260.026*
C760.6184 (3)0.2118 (3)0.3918 (2)0.0250 (6)
H76A0.6099560.1699720.4441240.030*
H76B0.7244070.2511450.3994390.030*
C770.5282 (3)0.0996 (3)0.2927 (2)0.0236 (6)
H77A0.5703260.0299330.2868820.028*
H77B0.4246100.0522600.2884120.028*
C780.5282 (3)0.1592 (3)0.2092 (2)0.0208 (6)
H78A0.6326220.1999430.2115950.025*
C790.4734 (4)0.2731 (3)0.2185 (2)0.0253 (6)
H79A0.3674200.2331050.2107250.030*
H79B0.4817470.3145940.1660120.030*
C800.5637 (4)0.3857 (3)0.3178 (2)0.0262 (7)
H80A0.6669990.4336050.3218840.031*
H80B0.5208890.4549310.3235140.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0177 (3)0.0172 (3)0.0191 (4)0.0079 (3)0.0094 (3)0.0065 (3)
P20.0171 (3)0.0172 (3)0.0191 (4)0.0075 (3)0.0086 (3)0.0052 (3)
O10.0211 (10)0.0248 (10)0.0307 (12)0.0116 (8)0.0137 (9)0.0102 (9)
O20.0166 (10)0.0260 (10)0.0271 (11)0.0094 (8)0.0100 (9)0.0066 (8)
O30.0296 (11)0.0169 (9)0.0204 (10)0.0075 (8)0.0106 (9)0.0069 (8)
O40.0264 (10)0.0177 (9)0.0216 (10)0.0080 (8)0.0112 (9)0.0075 (8)
O50.0203 (10)0.0184 (10)0.0185 (10)0.0059 (8)0.0072 (8)0.0052 (8)
O60.0294 (11)0.0246 (10)0.0250 (11)0.0153 (9)0.0177 (9)0.0116 (9)
N10.0147 (11)0.0212 (12)0.0198 (12)0.0086 (9)0.0051 (10)0.0047 (9)
N20.0152 (11)0.0238 (12)0.0183 (13)0.0090 (10)0.0061 (10)0.0018 (10)
C10.0250 (14)0.0176 (13)0.0173 (14)0.0077 (11)0.0084 (12)0.0067 (11)
C20.0204 (14)0.0300 (15)0.0221 (15)0.0094 (12)0.0103 (12)0.0106 (12)
C30.0387 (17)0.0293 (16)0.0355 (17)0.0225 (14)0.0185 (15)0.0183 (13)
C40.0380 (18)0.0260 (15)0.0398 (19)0.0109 (14)0.0183 (16)0.0178 (14)
C50.0276 (16)0.0381 (18)0.045 (2)0.0118 (14)0.0199 (15)0.0244 (15)
C60.0280 (16)0.0335 (17)0.0328 (17)0.0169 (13)0.0170 (14)0.0171 (14)
C70.0230 (14)0.0226 (14)0.0295 (16)0.0138 (11)0.0162 (13)0.0140 (12)
C80.0305 (15)0.0221 (14)0.0324 (17)0.0103 (12)0.0136 (14)0.0102 (13)
C90.0376 (18)0.0250 (16)0.054 (2)0.0129 (14)0.0212 (17)0.0211 (15)
C100.0331 (17)0.0364 (18)0.052 (2)0.0198 (14)0.0238 (16)0.0307 (16)
C110.0286 (16)0.0454 (19)0.0320 (17)0.0209 (14)0.0134 (14)0.0214 (15)
C120.0274 (16)0.0265 (15)0.0296 (17)0.0129 (12)0.0105 (13)0.0122 (12)
C130.0193 (13)0.0171 (13)0.0184 (14)0.0026 (11)0.0050 (11)0.0034 (11)
C140.0273 (15)0.0268 (15)0.0316 (16)0.0114 (12)0.0149 (13)0.0119 (12)
C150.0395 (18)0.0286 (16)0.049 (2)0.0194 (14)0.0214 (17)0.0197 (15)
C160.044 (2)0.0348 (18)0.045 (2)0.0165 (15)0.0231 (17)0.0269 (16)
C170.0380 (18)0.0365 (18)0.0378 (19)0.0131 (15)0.0241 (16)0.0162 (14)
C180.0263 (15)0.0258 (15)0.0312 (17)0.0102 (12)0.0136 (13)0.0095 (12)
C190.0228 (14)0.0264 (15)0.0176 (14)0.0127 (12)0.0106 (12)0.0098 (11)
C200.0279 (15)0.0261 (15)0.0278 (16)0.0089 (12)0.0122 (13)0.0125 (12)
C210.0281 (16)0.0450 (19)0.0334 (18)0.0153 (14)0.0162 (14)0.0205 (15)
C220.0337 (17)0.054 (2)0.0248 (16)0.0254 (16)0.0171 (14)0.0153 (15)
C230.0305 (17)0.0387 (18)0.0246 (16)0.0137 (14)0.0081 (14)0.0000 (13)
C240.0248 (15)0.0274 (16)0.0282 (17)0.0067 (13)0.0102 (13)0.0047 (13)
C260.0266 (15)0.0182 (13)0.0229 (15)0.0085 (12)0.0119 (13)0.0072 (11)
C270.0287 (16)0.0240 (14)0.0191 (15)0.0101 (12)0.0114 (13)0.0092 (12)
C280.0176 (13)0.0207 (13)0.0158 (14)0.0097 (11)0.0050 (12)0.0038 (11)
C290.0225 (15)0.0192 (13)0.0217 (15)0.0080 (11)0.0121 (12)0.0066 (11)
C300.0227 (14)0.0206 (13)0.0175 (14)0.0092 (11)0.0110 (12)0.0073 (11)
C320.0180 (13)0.0208 (14)0.0178 (14)0.0085 (11)0.0065 (12)0.0043 (11)
P510.0151 (3)0.0249 (4)0.0223 (4)0.0076 (3)0.0072 (3)0.0044 (3)
P520.0166 (3)0.0305 (4)0.0196 (4)0.0104 (3)0.0086 (3)0.0082 (3)
O510.0185 (10)0.0399 (12)0.0267 (11)0.0142 (9)0.0084 (9)0.0086 (9)
O520.0192 (10)0.0353 (12)0.0271 (11)0.0128 (9)0.0115 (9)0.0103 (9)
O530.0225 (10)0.0226 (10)0.0258 (11)0.0058 (8)0.0069 (9)0.0060 (8)
O540.0252 (10)0.0254 (11)0.0304 (12)0.0123 (9)0.0150 (9)0.0094 (9)
O550.0282 (11)0.0504 (14)0.0277 (12)0.0224 (10)0.0146 (10)0.0183 (10)
O560.0323 (12)0.0275 (11)0.0274 (12)0.0096 (9)0.0138 (10)0.0025 (9)
N510.0135 (12)0.0325 (14)0.0257 (14)0.0059 (10)0.0067 (11)0.0001 (11)
N520.0141 (11)0.0234 (12)0.0265 (14)0.0043 (10)0.0105 (11)0.0058 (10)
C510.0236 (15)0.0243 (14)0.0310 (17)0.0095 (12)0.0155 (13)0.0100 (12)
C520.0368 (18)0.0361 (18)0.0299 (18)0.0116 (15)0.0099 (15)0.0091 (14)
C530.060 (2)0.046 (2)0.045 (2)0.0275 (18)0.030 (2)0.0273 (18)
C540.063 (2)0.0303 (18)0.062 (3)0.0204 (17)0.043 (2)0.0210 (17)
C550.062 (2)0.0265 (17)0.048 (2)0.0072 (16)0.029 (2)0.0058 (16)
C560.0403 (19)0.0308 (17)0.0317 (18)0.0086 (14)0.0180 (15)0.0065 (14)
C570.0224 (14)0.0263 (14)0.0272 (16)0.0140 (12)0.0122 (12)0.0133 (12)
C580.0227 (15)0.0268 (15)0.0316 (18)0.0101 (12)0.0101 (14)0.0078 (13)
C590.0321 (17)0.0324 (16)0.0294 (17)0.0168 (14)0.0123 (14)0.0118 (13)
C600.0333 (17)0.0410 (18)0.0344 (18)0.0214 (14)0.0203 (15)0.0214 (14)
C610.0269 (16)0.0405 (18)0.041 (2)0.0119 (14)0.0179 (15)0.0226 (15)
C620.0252 (15)0.0265 (15)0.0305 (17)0.0056 (13)0.0081 (13)0.0097 (13)
C630.0168 (13)0.0283 (15)0.0190 (14)0.0073 (11)0.0051 (11)0.0074 (11)
C640.0277 (17)0.0321 (17)0.0323 (18)0.0105 (13)0.0136 (14)0.0071 (14)
C650.0346 (19)0.046 (2)0.0300 (18)0.0130 (16)0.0116 (15)0.0036 (15)
C660.0322 (18)0.054 (2)0.0297 (18)0.0084 (16)0.0102 (15)0.0137 (16)
C670.0351 (18)0.049 (2)0.0334 (19)0.0102 (16)0.0113 (15)0.0250 (16)
C680.0338 (18)0.0356 (18)0.0394 (19)0.0145 (15)0.0092 (15)0.0156 (15)
C690.0331 (17)0.0197 (15)0.0433 (19)0.0135 (13)0.0195 (15)0.0084 (13)
C700.039 (2)0.047 (2)0.077 (3)0.0283 (17)0.037 (2)0.033 (2)
C710.055 (3)0.094 (4)0.125 (5)0.057 (3)0.056 (3)0.083 (4)
C720.068 (3)0.100 (4)0.133 (5)0.061 (3)0.068 (3)0.100 (4)
C730.052 (2)0.058 (2)0.099 (4)0.038 (2)0.052 (3)0.054 (3)
C740.0324 (17)0.0338 (17)0.059 (2)0.0204 (14)0.0250 (17)0.0248 (16)
C750.0161 (14)0.0244 (14)0.0230 (16)0.0074 (11)0.0093 (12)0.0033 (12)
C760.0249 (15)0.0255 (14)0.0259 (16)0.0102 (12)0.0088 (13)0.0119 (12)
C770.0248 (15)0.0192 (14)0.0288 (16)0.0088 (12)0.0110 (13)0.0105 (12)
C780.0156 (13)0.0232 (14)0.0232 (16)0.0066 (11)0.0082 (12)0.0077 (12)
C790.0292 (16)0.0234 (14)0.0274 (16)0.0142 (12)0.0097 (13)0.0114 (12)
C800.0305 (17)0.0239 (15)0.0292 (17)0.0161 (13)0.0114 (14)0.0094 (13)
Geometric parameters (Å, º) top
P1—O11.463 (2)P51—O511.466 (2)
P1—O31.590 (2)P51—O531.585 (2)
P1—O41.5937 (19)P51—O541.590 (2)
P1—N11.609 (2)P51—N511.603 (3)
P2—O21.468 (2)P52—O521.468 (2)
P2—O61.580 (2)P52—O561.586 (2)
P2—O51.5900 (19)P52—O551.593 (2)
P2—N21.602 (2)P52—N521.595 (3)
O3—C11.415 (3)O53—C511.398 (3)
O4—C71.407 (3)O54—C571.405 (4)
O5—C131.406 (3)O55—C631.397 (4)
O6—C191.411 (3)O56—C691.404 (4)
N1—C321.473 (4)N51—C751.467 (4)
N1—H1N0.85 (2)N51—H51N0.87 (2)
N2—C281.464 (3)N52—C781.468 (4)
N2—H2N0.85 (2)N52—H52N0.84 (2)
C1—C21.375 (4)C51—C561.368 (4)
C1—C61.378 (4)C51—C521.380 (5)
C2—C31.385 (4)C52—C531.390 (5)
C2—H2C0.9500C52—H52C0.9500
C3—C41.390 (5)C53—C541.378 (6)
C3—H3A0.9500C53—H53A0.9500
C4—C51.379 (5)C54—C551.378 (6)
C4—H4A0.9500C54—H54A0.9500
C5—C61.387 (4)C55—C561.389 (5)
C5—H5A0.9500C55—H55A0.9500
C6—H6A0.9500C56—H56A0.9500
C7—C121.375 (4)C57—C581.378 (4)
C7—C81.385 (4)C57—C621.381 (4)
C8—C91.393 (4)C58—C591.380 (5)
C8—H8A0.9500C58—H58A0.9500
C9—C101.375 (5)C59—C601.389 (5)
C9—H9A0.9500C59—H59A0.9500
C10—C111.382 (5)C60—C611.375 (5)
C10—H10A0.9500C60—H60A0.9500
C11—C121.390 (4)C61—C621.381 (5)
C11—H11A0.9500C61—H61A0.9500
C12—H12A0.9500C62—H62A0.9500
C13—C141.381 (4)C63—C641.373 (5)
C13—C181.382 (4)C63—C681.388 (5)
C14—C151.382 (4)C64—C651.387 (5)
C14—H14A0.9500C64—H64A0.9500
C15—C161.385 (5)C65—C661.372 (6)
C15—H15A0.9500C65—H65A0.9500
C16—C171.389 (5)C66—C671.379 (6)
C16—H16A0.9500C66—H66A0.9500
C17—C181.382 (5)C67—C681.400 (5)
C17—H17A0.9500C67—H67A0.9500
C18—H18A0.9500C68—H68A0.9500
C19—C241.375 (4)C69—C701.371 (5)
C19—C201.383 (4)C69—C741.384 (5)
C20—C211.385 (4)C70—C711.375 (6)
C20—H20A0.9500C70—H70A0.9500
C21—C221.373 (5)C71—C721.393 (6)
C21—H21A0.9500C71—H71A0.9500
C22—C231.389 (5)C72—C731.372 (6)
C22—H22A0.9500C72—H72A0.9500
C23—C241.381 (5)C73—C741.375 (5)
C23—H23A0.9500C73—H73A0.9500
C24—H24A0.9500C74—H74A0.9500
C26—C271.523 (4)C75—C761.523 (4)
C26—C321.524 (4)C75—C801.523 (4)
C26—H26A0.9900C75—H75A1.0000
C26—H26B0.9900C76—C771.528 (4)
C27—C281.522 (4)C76—H76A0.9900
C27—H27A0.9900C76—H76B0.9900
C27—H27B0.9900C77—C781.518 (4)
C28—C291.520 (4)C77—H77A0.9900
C28—H28A1.0000C77—H77B0.9900
C29—C301.525 (4)C78—C791.518 (4)
C29—H29A0.9900C78—H78A1.0000
C29—H29B0.9900C79—C801.533 (4)
C30—C321.529 (4)C79—H79A0.9900
C30—H30A0.9900C79—H79B0.9900
C30—H30B0.9900C80—H80A0.9900
C32—H32A1.0000C80—H80B0.9900
O1—P1—O3115.74 (12)O51—P51—O53115.32 (12)
O1—P1—O4114.34 (12)O51—P51—O54112.46 (12)
O3—P1—O494.73 (10)O53—P51—O54100.97 (11)
O1—P1—N1113.23 (12)O51—P51—N51116.36 (14)
O3—P1—N1109.01 (12)O53—P51—N51104.92 (12)
O4—P1—N1108.18 (12)O54—P51—N51105.21 (13)
O2—P2—O6113.89 (12)O52—P52—O56114.91 (13)
O2—P2—O5115.07 (12)O52—P52—O55113.48 (12)
O6—P2—O5100.23 (11)O56—P52—O55100.21 (13)
O2—P2—N2114.21 (13)O52—P52—N52114.76 (12)
O6—P2—N2106.65 (12)O56—P52—N52107.10 (12)
O5—P2—N2105.44 (11)O55—P52—N52104.95 (13)
C1—O3—P1116.03 (17)C51—O53—P51126.20 (19)
C7—O4—P1123.86 (18)C57—O54—P51121.73 (19)
C13—O5—P2118.23 (17)C63—O55—P52123.82 (19)
C19—O6—P2122.84 (18)C69—O56—P52119.24 (19)
C32—N1—P1124.40 (19)C75—N51—P51123.7 (2)
C32—N1—H1N113 (2)C75—N51—H51N119 (2)
P1—N1—H1N119 (2)P51—N51—H51N116 (2)
C28—N2—P2124.3 (2)C78—N52—P52125.6 (2)
C28—N2—H2N115 (2)C78—N52—H52N114 (2)
P2—N2—H2N118 (2)P52—N52—H52N120 (2)
C2—C1—C6122.0 (3)C56—C51—C52121.5 (3)
C2—C1—O3118.5 (2)C56—C51—O53115.1 (3)
C6—C1—O3119.5 (3)C52—C51—O53123.5 (3)
C1—C2—C3119.0 (3)C51—C52—C53118.8 (3)
C1—C2—H2C120.5C51—C52—H52C120.6
C3—C2—H2C120.5C53—C52—H52C120.6
C2—C3—C4120.0 (3)C54—C53—C52120.4 (4)
C2—C3—H3A120.0C54—C53—H53A119.8
C4—C3—H3A120.0C52—C53—H53A119.8
C5—C4—C3119.9 (3)C55—C54—C53119.7 (3)
C5—C4—H4A120.0C55—C54—H54A120.1
C3—C4—H4A120.0C53—C54—H54A120.1
C4—C5—C6120.5 (3)C54—C55—C56120.4 (3)
C4—C5—H5A119.8C54—C55—H55A119.8
C6—C5—H5A119.8C56—C55—H55A119.8
C1—C6—C5118.6 (3)C51—C56—C55119.2 (3)
C1—C6—H6A120.7C51—C56—H56A120.4
C5—C6—H6A120.7C55—C56—H56A120.4
C12—C7—C8121.7 (3)C58—C57—C62121.3 (3)
C12—C7—O4123.8 (3)C58—C57—O54120.4 (3)
C8—C7—O4114.5 (3)C62—C57—O54118.1 (3)
C7—C8—C9118.5 (3)C57—C58—C59119.0 (3)
C7—C8—H8A120.8C57—C58—H58A120.5
C9—C8—H8A120.8C59—C58—H58A120.5
C10—C9—C8120.5 (3)C58—C59—C60120.6 (3)
C10—C9—H9A119.7C58—C59—H59A119.7
C8—C9—H9A119.7C60—C59—H59A119.7
C9—C10—C11120.1 (3)C61—C60—C59119.3 (3)
C9—C10—H10A119.9C61—C60—H60A120.4
C11—C10—H10A119.9C59—C60—H60A120.4
C10—C11—C12120.2 (3)C60—C61—C62121.0 (3)
C10—C11—H11A119.9C60—C61—H61A119.5
C12—C11—H11A119.9C62—C61—H61A119.5
C7—C12—C11118.9 (3)C57—C62—C61118.8 (3)
C7—C12—H12A120.5C57—C62—H62A120.6
C11—C12—H12A120.5C61—C62—H62A120.6
C14—C13—C18122.3 (3)C64—C63—C68120.6 (3)
C14—C13—O5118.3 (3)C64—C63—O55122.0 (3)
C18—C13—O5119.4 (3)C68—C63—O55117.4 (3)
C13—C14—C15118.3 (3)C63—C64—C65120.7 (3)
C13—C14—H14A120.8C63—C64—H64A119.7
C15—C14—H14A120.8C65—C64—H64A119.7
C14—C15—C16120.7 (3)C66—C65—C64118.7 (4)
C14—C15—H15A119.6C66—C65—H65A120.6
C16—C15—H15A119.6C64—C65—H65A120.6
C15—C16—C17119.7 (3)C65—C66—C67121.8 (3)
C15—C16—H16A120.1C65—C66—H66A119.1
C17—C16—H16A120.1C67—C66—H66A119.1
C18—C17—C16120.5 (3)C66—C67—C68119.2 (3)
C18—C17—H17A119.8C66—C67—H67A120.4
C16—C17—H17A119.8C68—C67—H67A120.4
C13—C18—C17118.5 (3)C63—C68—C67119.0 (3)
C13—C18—H18A120.8C63—C68—H68A120.5
C17—C18—H18A120.8C67—C68—H68A120.5
C24—C19—C20121.9 (3)C70—C69—C74121.1 (3)
C24—C19—O6120.8 (2)C70—C69—O56121.0 (3)
C20—C19—O6117.2 (2)C74—C69—O56117.8 (3)
C19—C20—C21118.4 (3)C69—C70—C71119.4 (3)
C19—C20—H20A120.8C69—C70—H70A120.3
C21—C20—H20A120.8C71—C70—H70A120.3
C22—C21—C20120.7 (3)C70—C71—C72119.9 (4)
C22—C21—H21A119.6C70—C71—H71A120.1
C20—C21—H21A119.6C72—C71—H71A120.1
C21—C22—C23119.9 (3)C73—C72—C71120.1 (4)
C21—C22—H22A120.1C73—C72—H72A120.0
C23—C22—H22A120.1C71—C72—H72A120.0
C24—C23—C22120.3 (3)C72—C73—C74120.2 (4)
C24—C23—H23A119.9C72—C73—H73A119.9
C22—C23—H23A119.9C74—C73—H73A119.9
C19—C24—C23118.8 (3)C73—C74—C69119.2 (3)
C19—C24—H24A120.6C73—C74—H74A120.4
C23—C24—H24A120.6C69—C74—H74A120.4
C27—C26—C32111.1 (2)N51—C75—C76110.4 (2)
C27—C26—H26A109.4N51—C75—C80110.1 (2)
C32—C26—H26A109.4C76—C75—C80110.9 (2)
C27—C26—H26B109.4N51—C75—H75A108.4
C32—C26—H26B109.4C76—C75—H75A108.4
H26A—C26—H26B108.0C80—C75—H75A108.4
C28—C27—C26111.2 (2)C75—C76—C77111.7 (2)
C28—C27—H27A109.4C75—C76—H76A109.3
C26—C27—H27A109.4C77—C76—H76A109.3
C28—C27—H27B109.4C75—C76—H76B109.3
C26—C27—H27B109.4C77—C76—H76B109.3
H27A—C27—H27B108.0H76A—C76—H76B108.0
N2—C28—C29109.6 (2)C78—C77—C76111.8 (2)
N2—C28—C27112.2 (2)C78—C77—H77A109.3
C29—C28—C27110.8 (2)C76—C77—H77A109.3
N2—C28—H28A108.0C78—C77—H77B109.3
C29—C28—H28A108.0C76—C77—H77B109.3
C27—C28—H28A108.0H77A—C77—H77B107.9
C28—C29—C30111.6 (2)N52—C78—C79110.2 (2)
C28—C29—H29A109.3N52—C78—C77110.6 (2)
C30—C29—H29A109.3C79—C78—C77111.2 (3)
C28—C29—H29B109.3N52—C78—H78A108.2
C30—C29—H29B109.3C79—C78—H78A108.2
H29A—C29—H29B108.0C77—C78—H78A108.2
C29—C30—C32111.8 (2)C78—C79—C80111.1 (3)
C29—C30—H30A109.3C78—C79—H79A109.4
C32—C30—H30A109.3C80—C79—H79A109.4
C29—C30—H30B109.3C78—C79—H79B109.4
C32—C30—H30B109.3C80—C79—H79B109.4
H30A—C30—H30B107.9H79A—C79—H79B108.0
N1—C32—C26109.4 (2)C75—C80—C79112.2 (2)
N1—C32—C30110.6 (2)C75—C80—H80A109.2
C26—C32—C30111.2 (2)C79—C80—H80A109.2
N1—C32—H32A108.5C75—C80—H80B109.2
C26—C32—H32A108.5C79—C80—H80B109.2
C30—C32—H32A108.5H80A—C80—H80B107.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O52i0.85 (2)2.03 (2)2.863 (3)167 (3)
N2—H2N···O510.85 (2)2.00 (2)2.820 (3)162 (3)
N51—H51N···O2ii0.87 (2)1.98 (3)2.802 (3)158 (3)
N52—H52N···O10.84 (2)2.04 (2)2.866 (3)168 (3)
C22—H22A···O4iii0.952.513.418 (4)160
C6—H6A···O550.952.693.565 (4)154
C74—H74A···O10.952.613.329 (4)133
C2—H2C···O52i0.952.693.465 (3)139
C2—H2C···CG1i0.952.923.593 (8)129
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y+1, z+1.
N,N'-(1,4-Phenylene)bis(O,O'-dimethylthiophosphoramidate) (bv18) top
Crystal data top
C10H18N2O4P2S2F(000) = 744
Mr = 356.32Dx = 1.388 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 13.2517 (3) ÅCell parameters from 6840 reflections
b = 10.0091 (2) Åθ = 3.1–28.0°
c = 13.9580 (3) ŵ = 0.51 mm1
β = 112.9309 (12)°T = 295 K
V = 1705.05 (6) Å3Block, colourless
Z = 40.43 × 0.36 × 0.31 mm
Data collection top
Nonius KappaCCD
diffractometer
3267 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
φ scans and ω scansθmax = 28.0°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1717
Tmin = 0.790, Tmax = 0.845k = 1213
6840 measured reflectionsl = 1818
4091 independent reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.9571P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4091 reflectionsΔρmax = 0.70 e Å3
191 parametersΔρmin = 0.48 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.10510 (16)0.22673 (18)0.16416 (14)0.0383 (4)
C20.05330 (16)0.33804 (19)0.22145 (15)0.0406 (4)
H20.0804890.4227410.1977830.049*
C30.03820 (16)0.3252 (2)0.31329 (15)0.0432 (5)
H30.0718660.4009460.3507640.052*
C40.07964 (16)0.19929 (19)0.34936 (15)0.0401 (4)
C50.03004 (16)0.0882 (2)0.29087 (15)0.0442 (5)
H50.0585100.0037160.3136780.053*
C60.06154 (17)0.10094 (19)0.19870 (15)0.0441 (5)
H60.0937400.0254120.1600880.053*
N10.19948 (15)0.24601 (16)0.07154 (14)0.0491 (5)
H1N0.218 (2)0.3233 (18)0.060 (2)0.059*
P10.27879 (4)0.13688 (5)0.00992 (4)0.03875 (14)
S10.39878 (5)0.22087 (6)0.11912 (5)0.05876 (19)
O10.20470 (13)0.04058 (16)0.04448 (12)0.0535 (4)
C70.1410 (3)0.0939 (5)0.0986 (3)0.1061 (13)
H7A0.1854120.1536690.1522170.159*
H7B0.1158290.0220730.1292600.159*
H7C0.0790750.1414950.0504870.159*
O20.30821 (13)0.02609 (16)0.05507 (12)0.0553 (4)
C80.3725 (3)0.0616 (4)0.1146 (3)0.0930 (11)
H8A0.3353790.1302670.1637260.140*
H8B0.3819000.0155870.1510650.140*
H8C0.4429690.0938270.0684150.140*
N20.17100 (16)0.18068 (18)0.44518 (14)0.0541 (5)
H2N0.188 (2)0.0995 (18)0.460 (2)0.065*
P20.24331 (4)0.28916 (5)0.53117 (4)0.04238 (15)
S20.35199 (5)0.20676 (7)0.65024 (5)0.0634 (2)
O30.28520 (14)0.39623 (18)0.47204 (13)0.0635 (4)
C90.3563 (4)0.3603 (6)0.4224 (3)0.1276 (17)
H9A0.4279430.3419520.4740350.191*
H9B0.3606010.4324790.3788880.191*
H9C0.3284740.2820300.3806400.191*
O40.16411 (17)0.3914 (2)0.55171 (14)0.0803 (6)
C100.1129 (4)0.3727 (6)0.6169 (4)0.152 (2)
H10A0.1472020.3005510.6635160.228*
H10B0.0373200.3513150.5775020.228*
H10C0.1175100.4528520.6561210.228*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0372 (10)0.0324 (9)0.0343 (9)0.0009 (7)0.0021 (8)0.0010 (7)
C20.0435 (10)0.0282 (8)0.0395 (10)0.0019 (8)0.0046 (8)0.0011 (8)
C30.0459 (11)0.0317 (9)0.0397 (10)0.0028 (8)0.0033 (8)0.0040 (8)
C40.0369 (10)0.0365 (9)0.0345 (9)0.0010 (8)0.0005 (8)0.0003 (8)
C50.0461 (11)0.0307 (9)0.0426 (10)0.0051 (8)0.0027 (8)0.0010 (8)
C60.0472 (11)0.0305 (9)0.0401 (10)0.0007 (8)0.0012 (8)0.0040 (8)
N10.0479 (10)0.0277 (8)0.0458 (9)0.0019 (7)0.0100 (8)0.0005 (7)
P10.0376 (3)0.0323 (3)0.0363 (3)0.00116 (19)0.0034 (2)0.0027 (2)
S10.0486 (3)0.0500 (3)0.0506 (3)0.0034 (2)0.0103 (2)0.0014 (3)
O10.0531 (9)0.0547 (9)0.0502 (8)0.0068 (7)0.0172 (7)0.0068 (7)
C70.094 (2)0.145 (3)0.104 (3)0.021 (2)0.065 (2)0.021 (3)
O20.0567 (9)0.0503 (9)0.0557 (9)0.0091 (7)0.0183 (7)0.0048 (7)
C80.092 (2)0.125 (3)0.0770 (19)0.020 (2)0.0494 (18)0.000 (2)
N20.0529 (11)0.0343 (9)0.0469 (10)0.0037 (8)0.0114 (8)0.0006 (8)
P20.0421 (3)0.0426 (3)0.0335 (3)0.0027 (2)0.0050 (2)0.0046 (2)
S20.0600 (4)0.0617 (4)0.0421 (3)0.0054 (3)0.0089 (3)0.0022 (3)
O30.0650 (10)0.0615 (10)0.0548 (9)0.0133 (9)0.0134 (8)0.0006 (8)
C90.111 (3)0.191 (5)0.108 (3)0.007 (3)0.073 (3)0.016 (3)
O40.0843 (13)0.0981 (15)0.0541 (10)0.0405 (12)0.0220 (9)0.0052 (10)
C100.128 (4)0.238 (6)0.122 (3)0.063 (4)0.085 (3)0.007 (4)
Geometric parameters (Å, º) top
C1—C21.387 (3)C7—H7B0.9600
C1—C61.391 (3)C7—H7C0.9600
C1—N11.419 (2)O2—C81.447 (3)
C2—C31.385 (3)C8—H8A0.9600
C2—H20.9300C8—H8B0.9600
C3—C41.389 (3)C8—H8C0.9600
C3—H30.9300N2—P21.6253 (18)
C4—C51.385 (3)N2—H2N0.847 (17)
C4—N21.424 (2)P2—O41.5702 (18)
C5—C61.388 (3)P2—O31.5794 (18)
C5—H50.9300P2—S21.9109 (8)
C6—H60.9300O3—C91.416 (4)
N1—P11.6307 (17)C9—H9A0.9600
N1—H1N0.807 (16)C9—H9B0.9600
P1—O21.5749 (16)C9—H9C0.9600
P1—O11.5795 (16)O4—C101.343 (4)
P1—S11.9156 (7)C10—H10A0.9600
O1—C71.437 (3)C10—H10B0.9600
C7—H7A0.9600C10—H10C0.9600
C2—C1—C6118.81 (17)H7A—C7—H7C109.5
C2—C1—N1118.59 (17)H7B—C7—H7C109.5
C6—C1—N1122.59 (17)C8—O2—P1119.39 (19)
C3—C2—C1121.15 (18)O2—C8—H8A109.5
C3—C2—H2119.4O2—C8—H8B109.5
C1—C2—H2119.4H8A—C8—H8B109.5
C2—C3—C4119.95 (18)O2—C8—H8C109.5
C2—C3—H3120.0H8A—C8—H8C109.5
C4—C3—H3120.0H8B—C8—H8C109.5
C5—C4—C3119.05 (17)C4—N2—P2130.33 (15)
C5—C4—N2118.90 (17)C4—N2—H2N113.7 (19)
C3—C4—N2122.05 (17)P2—N2—H2N115.9 (18)
C4—C5—C6121.01 (18)O4—P2—O392.82 (12)
C4—C5—H5119.5O4—P2—N2109.06 (11)
C6—C5—H5119.5O3—P2—N2107.07 (10)
C5—C6—C1119.96 (18)O4—P2—S2116.96 (8)
C5—C6—H6120.0O3—P2—S2116.63 (7)
C1—C6—H6120.0N2—P2—S2112.43 (7)
C1—N1—P1130.09 (14)C9—O3—P2121.3 (3)
C1—N1—H1N113.4 (19)O3—C9—H9A109.5
P1—N1—H1N116.4 (19)O3—C9—H9B109.5
O2—P1—O193.96 (9)H9A—C9—H9B109.5
O2—P1—N1107.88 (10)O3—C9—H9C109.5
O1—P1—N1108.26 (10)H9A—C9—H9C109.5
O2—P1—S1116.89 (7)H9B—C9—H9C109.5
O1—P1—S1116.54 (7)C10—O4—P2125.7 (3)
N1—P1—S1111.75 (7)O4—C10—H10A109.5
C7—O1—P1119.8 (2)O4—C10—H10B109.5
O1—C7—H7A109.5H10A—C10—H10B109.5
O1—C7—H7B109.5O4—C10—H10C109.5
H7A—C7—H7B109.5H10A—C10—H10C109.5
O1—C7—H7C109.5H10B—C10—H10C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O30.932.673.237 (2)120
C3—H3···O40.932.593.158 (3)120
N1—H1N···O1i0.81 (2)2.38 (2)3.174 (2)169 (2)
N2—H2N···O3ii0.85 (2)2.22 (2)3.042 (3)165 (2)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y1/2, z+1.
All the POC bond angles and the contribution portions of s and p orbitals of BD(P-O) and BD(C-O) in both (I) and (II) top
Compound (I)
SegmentBond angles (°)BD(P-O)Contribution portions (%)BD(C-O)Contribution portions (%)
P1O3C1125.0815BD(P1-O3)s (26.17), p (73.79)BD(O3-C1)s (37.13), p (62.81)
P1O4C7124.7019BD(P1-O4s (27.14), p (72.82)BD(O4-C7)s (37.20), p (62.75)
P2O5C13125.0868BD(P2-O5)s (28.18), p (71.78)BD(O5-C13)s (37.94), p (62.01)
P2O6C19122.9743BD(P2-O6)s (27.10), p (72.85)BD(O6-C19)s (37.33), p (62.62)
P51O53C51125.6914BD(P51-O53)s (27.28), p (72.67)BD(O53-C51)s (37.88), p (62.07)
P51O54C57124.4525BD(P51-O54)s (25.76), p (74.19)BD(O54-C57)s (36.49), p (63.45)
P52O55C63124.3808BD(P52-O56)s (26.58), p (73.38)BD(O55-C63)s (36.89), p (63.0 6)
P52O56C69124.7025BD(P52-O55)s (26.48), p (73.47)BD(O56-C69)s (37.31), p (62.63)
Compound (II)
SegmentBond angles (?)BD(P-O)Contribution portions (%)BD(C-O)Contribution portions (%)
P1O1C7120.6189BDP1-O1s (28.60), p (71.35)BD(O1-C7)s (30.69), p (69.25)
P1O2C8120.5541BDP1-O2s (28.58), p (71.37)BD(O2-C8)s (30.67), p (69.28)
P2O3C9120.5650BDP2-O3s (28.58), p (71.37)BD(O3-C9)s (30.67), p (69.27)
P2O4C10120.6046BDP2-O4s (28.59), p (71.36)BD(O4-C10)s (30.69), p (69.26)
The contribution portions of s and p orbitals of two lone pair at O atoms top
(I)
LP OContribution portions (%)π OContribution portions (%)
LP O3s (32.03), p (67.94)π O3s (4.65), p (95.32)
LP O4s (32.68), p (67.29)π O4s (2.97), p (96.99)
LP O5s (32.33), p (67.64)π O5s (1.54), p (98.42)
LP O6s (31.53), p (68.43)π O6s (4.01), p (95.95)
LP O53s (32.53), p (67.44)π O53s (2.30), p (97.67)
LP O54s (32.98), p (66.99)π O54s (4.75), p (95.22)
LP O55s (32.98), p (66.98)π O55s (3.53), p (96.43)
LP O56s (32.23), p (67.74)π O56s (3.95), p (96.01)
(II)
LP O1s (40.54), p (59.43)π O1s (0.15), p (99.81)
LP O2s (40.56), p (59.41)π O2s (0.18), p (99.78)
LP O3s (40.55), p (59.41)π O3s (0.17), p (99.79)
LP O4s (40.54), p (59.42)π O4s (0.16), p (99.80)
NBO analysis results of (I) at the B3LYP/6-311g(d,p) method top
DonorOccu. NoE (a.u.)AcceptorOccu. NoE (a.u.)E(2) (kcal mol-1)
LP O521.9660-0.7549BD*(1) N1—H1N0.02870.46237.09
LP O511.9662-0.7572BD*(1) N2—H2N0.02870.46427.03
LP O11.9638-0.7389BD*(1) N52—H52N0.03250.47298.60
LP O21.9656-0.7430BD*(1) N51—H51N0.03030.46767.33
NBO analysis results of (II) at the B3LYP/6-311g(d,p) method top
DonorOccu. NoE (a.u.)AcceptorOccu. NoE (a.u.)E(2) (kcal mol-1)
LP O11.94905-0.65940BD*(1) N1—H1N0.024260.427904.88
LP O31.94410-0.65654BD*(1) N2—H2N0.030070.428258.16
NBO analysis results of (I) at the B3LYP/6-311g(d,p) method (optimization is with restriction) top
DonorOccu. NoE (a.u.)AcceptorOccu. NoE (a.u.)E(2) (kcal mol-1)
LP O511.9556-0.8519BD*(1) N1—H1N0.04220.455712.86
LP O521.9544-0.8285BD*(1) N2—H2N0.04550.467213.87
LP O11.9567-0.8287BD*(1) N52—H52N0.04270.467213.41
LP O21.9536-0.8534BD*(1) N51—H51N0.04860.451714.21
 

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