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The crystal structures of
N,
N′-(cyclohexane-1,4-diyl)bis(
O,
O′-diphenylphosphoramide), C
30H
32N
2O
6P
2 or (C
6H
5O)
2P(O)(1-NH)(C
6H
10)(4-NH)P(O)(OC
6H
5)
2, (
I), and
N,
N′-(1,4-phenylene)bis(
O,
O′-dimethylthiophosphoramide), C
10H
18N
2O
4P
2S
2 or (CH
3O)
2P(S)(1-NH)(C
6H
4)(4-NH)P(S)(OCH
3)
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
CCDC references: 1405616; 1871198
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
C30H32N2O6P2 | Z = 2 |
Mr = 578.51 | F(000) = 608 |
Triclinic, P1 | Dx = 1.338 Mg m−3 |
a = 10.2789 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8253 (4) Å | Cell parameters from 12958 reflections |
c = 15.0200 (6) Å | θ = 3.2–29.8° |
α = 101.229 (4)° | µ = 0.20 mm−1 |
β = 105.716 (4)° | T = 120 K |
γ = 109.782 (4)° | Block, colourless |
V = 1436.22 (12) Å3 | 0.20 × 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 kW | Rint = 0.023 |
Profile data from ω–scans | θmax = 25.4°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −11→12 |
Tmin = 0.893, Tmax = 1.000 | k = −13→12 |
15732 measured reflections | l = −17→18 |
9396 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.01 | Δρmax = 0.40 e Å−3 |
9396 reflections | Δρmin = −0.30 e Å−3 |
733 parameters | Absolute structure: Flack x determined using 3782 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
7 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
P1 | −0.01942 (7) | −0.09038 (7) | 0.06356 (5) | 0.01710 (15) | |
P2 | 0.09162 (7) | 0.54319 (7) | 0.53492 (5) | 0.01731 (16) | |
O1 | 0.1377 (2) | −0.0603 (2) | 0.10889 (15) | 0.0237 (4) | |
O2 | −0.0577 (2) | 0.5311 (2) | 0.48320 (15) | 0.0229 (4) | |
O3 | −0.0683 (2) | −0.07426 (19) | −0.04192 (14) | 0.0224 (4) | |
O4 | −0.1284 (2) | −0.25020 (19) | 0.02886 (14) | 0.0215 (4) | |
O5 | 0.2148 (2) | 0.69728 (19) | 0.58839 (14) | 0.0198 (4) | |
O6 | 0.1030 (2) | 0.4849 (2) | 0.62401 (15) | 0.0228 (4) | |
N1 | −0.0773 (3) | −0.0049 (2) | 0.13168 (18) | 0.0188 (5) | |
H1N | −0.161 (3) | −0.003 (3) | 0.107 (2) | 0.023* | |
N2 | 0.1578 (3) | 0.4690 (2) | 0.46732 (17) | 0.0196 (5) | |
H2N | 0.248 (3) | 0.481 (3) | 0.492 (2) | 0.024* | |
C1 | −0.0099 (3) | 0.0619 (3) | −0.0466 (2) | 0.0200 (6) | |
C2 | −0.0984 (3) | 0.1332 (3) | −0.0525 (2) | 0.0235 (6) | |
H2C | −0.196901 | 0.091346 | −0.054063 | 0.028* | |
C3 | −0.0418 (4) | 0.2671 (3) | −0.0560 (2) | 0.0296 (7) | |
H3A | −0.101658 | 0.317639 | −0.060358 | 0.036* | |
C4 | 0.1026 (4) | 0.3275 (3) | −0.0533 (2) | 0.0332 (7) | |
H4A | 0.141577 | 0.419496 | −0.055456 | 0.040* | |
C5 | 0.1892 (4) | 0.2539 (4) | −0.0473 (3) | 0.0342 (8) | |
H5A | 0.288179 | 0.295787 | −0.044900 | 0.041* | |
C6 | 0.1330 (3) | 0.1192 (3) | −0.0449 (2) | 0.0278 (7) | |
H6A | 0.191672 | 0.067546 | −0.042118 | 0.033* | |
C7 | −0.1320 (3) | −0.3334 (3) | 0.0902 (2) | 0.0213 (6) | |
C8 | −0.2232 (3) | −0.4726 (3) | 0.0431 (2) | 0.0278 (7) | |
H8A | −0.277701 | −0.505712 | −0.025122 | 0.033* | |
C9 | −0.2331 (4) | −0.5628 (3) | 0.0981 (3) | 0.0367 (8) | |
H9A | −0.293877 | −0.658855 | 0.066975 | 0.044* | |
C10 | −0.1556 (4) | −0.5141 (4) | 0.1971 (3) | 0.0343 (8) | |
H10A | −0.163778 | −0.576278 | 0.234062 | 0.041* | |
C11 | −0.0659 (4) | −0.3747 (3) | 0.2428 (2) | 0.0317 (7) | |
H11A | −0.013364 | −0.341187 | 0.311247 | 0.038* | |
C12 | −0.0524 (3) | −0.2832 (3) | 0.1889 (2) | 0.0268 (6) | |
H12A | 0.010852 | −0.187684 | 0.219774 | 0.032* | |
C13 | 0.2305 (3) | 0.7902 (3) | 0.5343 (2) | 0.0205 (6) | |
C14 | 0.1535 (3) | 0.8727 (3) | 0.5368 (2) | 0.0272 (6) | |
H14A | 0.088763 | 0.864500 | 0.572182 | 0.033* | |
C15 | 0.1729 (4) | 0.9676 (3) | 0.4865 (3) | 0.0352 (8) | |
H15A | 0.121914 | 1.026139 | 0.487907 | 0.042* | |
C16 | 0.2659 (4) | 0.9782 (3) | 0.4340 (3) | 0.0374 (8) | |
H16A | 0.277387 | 1.042676 | 0.398768 | 0.045* | |
C17 | 0.3423 (4) | 0.8942 (3) | 0.4331 (3) | 0.0350 (8) | |
H17A | 0.407097 | 0.902204 | 0.397734 | 0.042* | |
C18 | 0.3249 (3) | 0.7991 (3) | 0.4832 (2) | 0.0272 (7) | |
H18A | 0.376589 | 0.741153 | 0.482568 | 0.033* | |
C19 | 0.0515 (3) | 0.5245 (3) | 0.6981 (2) | 0.0204 (6) | |
C20 | −0.0663 (3) | 0.4232 (3) | 0.7061 (2) | 0.0268 (6) | |
H20A | −0.114556 | 0.332794 | 0.660240 | 0.032* | |
C21 | −0.1122 (4) | 0.4568 (4) | 0.7824 (2) | 0.0330 (7) | |
H21A | −0.192378 | 0.388376 | 0.789429 | 0.040* | |
C22 | −0.0432 (4) | 0.5879 (4) | 0.8481 (2) | 0.0334 (7) | |
H22A | −0.075535 | 0.609828 | 0.900281 | 0.040* | |
C23 | 0.0739 (4) | 0.6883 (4) | 0.8382 (2) | 0.0334 (8) | |
H23A | 0.120862 | 0.779304 | 0.883214 | 0.040* | |
C24 | 0.1223 (3) | 0.6565 (3) | 0.7631 (2) | 0.0285 (7) | |
H24A | 0.203124 | 0.724589 | 0.756441 | 0.034* | |
C26 | −0.0522 (3) | 0.0945 (3) | 0.2995 (2) | 0.0220 (6) | |
H26A | −0.152266 | 0.093273 | 0.273895 | 0.026* | |
H26B | −0.063867 | 0.005809 | 0.312337 | 0.026* | |
C27 | 0.0411 (3) | 0.2137 (3) | 0.3943 (2) | 0.0232 (6) | |
H27A | −0.010222 | 0.204182 | 0.441290 | 0.028* | |
H27B | 0.137874 | 0.209769 | 0.423043 | 0.028* | |
C28 | 0.0674 (3) | 0.3527 (3) | 0.3772 (2) | 0.0181 (6) | |
H28A | −0.031368 | 0.356025 | 0.350978 | 0.022* | |
C29 | 0.1403 (3) | 0.3683 (3) | 0.3022 (2) | 0.0204 (6) | |
H29A | 0.241239 | 0.371807 | 0.328686 | 0.024* | |
H29B | 0.150183 | 0.456595 | 0.289110 | 0.024* | |
C30 | 0.0505 (3) | 0.2489 (3) | 0.2069 (2) | 0.0192 (6) | |
H30A | 0.105590 | 0.258315 | 0.162067 | 0.023* | |
H30B | −0.045086 | 0.253496 | 0.175647 | 0.023* | |
C32 | 0.0198 (3) | 0.1084 (3) | 0.2235 (2) | 0.0190 (6) | |
H32A | 0.116408 | 0.100391 | 0.247602 | 0.023* | |
P51 | 0.59715 (8) | 0.51364 (7) | 0.56468 (5) | 0.02132 (17) | |
P52 | 0.49858 (7) | −0.01130 (7) | 0.03851 (5) | 0.02157 (17) | |
O51 | 0.4625 (2) | 0.5299 (2) | 0.51600 (15) | 0.0280 (5) | |
O52 | 0.6611 (2) | 0.0448 (2) | 0.07061 (15) | 0.0260 (5) | |
O53 | 0.7353 (2) | 0.6527 (2) | 0.63427 (15) | 0.0254 (5) | |
O54 | 0.5762 (2) | 0.4288 (2) | 0.63893 (15) | 0.0253 (5) | |
O55 | 0.4222 (2) | 0.0145 (2) | −0.05940 (16) | 0.0318 (5) | |
O56 | 0.4173 (2) | −0.1749 (2) | 0.00698 (16) | 0.0302 (5) | |
N51 | 0.6598 (3) | 0.4376 (3) | 0.49526 (19) | 0.0265 (6) | |
H51N | 0.754 (3) | 0.479 (3) | 0.508 (3) | 0.032* | |
N52 | 0.4371 (3) | 0.0499 (2) | 0.11513 (19) | 0.0219 (5) | |
H52N | 0.346 (3) | 0.017 (3) | 0.105 (3) | 0.026* | |
C51 | 0.7833 (3) | 0.7776 (3) | 0.6141 (2) | 0.0250 (6) | |
C52 | 0.7386 (4) | 0.7885 (4) | 0.5217 (3) | 0.0360 (8) | |
H52C | 0.672085 | 0.708835 | 0.467307 | 0.043* | |
C53 | 0.7925 (5) | 0.9180 (4) | 0.5098 (3) | 0.0439 (9) | |
H53A | 0.762647 | 0.927119 | 0.446643 | 0.053* | |
C54 | 0.8891 (5) | 1.0332 (4) | 0.5889 (3) | 0.0459 (9) | |
H54A | 0.925727 | 1.121561 | 0.580353 | 0.055* | |
C55 | 0.9324 (5) | 1.0198 (4) | 0.6804 (3) | 0.0479 (10) | |
H55A | 0.999018 | 1.099197 | 0.734969 | 0.057* | |
C56 | 0.8793 (4) | 0.8910 (3) | 0.6933 (3) | 0.0354 (8) | |
H56A | 0.909342 | 0.881647 | 0.756331 | 0.043* | |
C57 | 0.5117 (3) | 0.4587 (3) | 0.7070 (2) | 0.0226 (6) | |
C58 | 0.5908 (3) | 0.5738 (3) | 0.7887 (2) | 0.0273 (7) | |
H58A | 0.687327 | 0.637050 | 0.797858 | 0.033* | |
C59 | 0.5276 (4) | 0.5959 (3) | 0.8571 (2) | 0.0298 (7) | |
H59A | 0.581000 | 0.675047 | 0.913608 | 0.036* | |
C60 | 0.3865 (4) | 0.5034 (3) | 0.8440 (2) | 0.0312 (7) | |
H60A | 0.343089 | 0.519239 | 0.890988 | 0.037* | |
C61 | 0.3105 (4) | 0.3885 (3) | 0.7623 (3) | 0.0341 (7) | |
H61A | 0.214524 | 0.324495 | 0.753476 | 0.041* | |
C62 | 0.3717 (3) | 0.3649 (3) | 0.6929 (2) | 0.0292 (7) | |
H62A | 0.318441 | 0.285618 | 0.636443 | 0.035* | |
C63 | 0.4746 (3) | 0.0130 (3) | −0.1361 (2) | 0.0223 (6) | |
C64 | 0.5044 (4) | −0.0946 (3) | −0.1764 (3) | 0.0311 (7) | |
H64A | 0.489926 | −0.170591 | −0.151648 | 0.037* | |
C65 | 0.5556 (4) | −0.0936 (4) | −0.2529 (3) | 0.0393 (8) | |
H65A | 0.578412 | −0.166997 | −0.279690 | 0.047* | |
C66 | 0.5725 (4) | 0.0155 (4) | −0.2890 (3) | 0.0416 (9) | |
H66A | 0.606502 | 0.016385 | −0.341821 | 0.050* | |
C67 | 0.5414 (4) | 0.1240 (4) | −0.2507 (3) | 0.0396 (8) | |
H67A | 0.553488 | 0.198339 | −0.277099 | 0.048* | |
C68 | 0.4919 (4) | 0.1234 (4) | −0.1726 (3) | 0.0366 (8) | |
H68A | 0.470542 | 0.197440 | −0.145023 | 0.044* | |
C69 | 0.4200 (4) | −0.2400 (3) | 0.0792 (3) | 0.0303 (7) | |
C70 | 0.5416 (4) | −0.2626 (4) | 0.1231 (3) | 0.0459 (10) | |
H70A | 0.626665 | −0.232796 | 0.105712 | 0.055* | |
C71 | 0.5393 (5) | −0.3287 (5) | 0.1924 (4) | 0.0706 (16) | |
H71A | 0.622447 | −0.345967 | 0.222593 | 0.085* | |
C72 | 0.4148 (5) | −0.3702 (6) | 0.2184 (5) | 0.0759 (17) | |
H72A | 0.414384 | −0.413225 | 0.267800 | 0.091* | |
C73 | 0.2929 (5) | −0.3492 (4) | 0.1727 (4) | 0.0550 (12) | |
H73A | 0.207170 | −0.379974 | 0.189258 | 0.066* | |
C74 | 0.2945 (4) | −0.2836 (3) | 0.1030 (3) | 0.0365 (8) | |
H74A | 0.210461 | −0.268358 | 0.071514 | 0.044* | |
C75 | 0.5652 (3) | 0.3272 (3) | 0.4023 (2) | 0.0217 (6) | |
H75A | 0.461588 | 0.287969 | 0.401526 | 0.026* | |
C76 | 0.6184 (3) | 0.2118 (3) | 0.3918 (2) | 0.0250 (6) | |
H76A | 0.609956 | 0.169972 | 0.444124 | 0.030* | |
H76B | 0.724407 | 0.251145 | 0.399439 | 0.030* | |
C77 | 0.5282 (3) | 0.0996 (3) | 0.2927 (2) | 0.0236 (6) | |
H77A | 0.570326 | 0.029933 | 0.286882 | 0.028* | |
H77B | 0.424610 | 0.052260 | 0.288412 | 0.028* | |
C78 | 0.5282 (3) | 0.1592 (3) | 0.2092 (2) | 0.0208 (6) | |
H78A | 0.632622 | 0.199943 | 0.211595 | 0.025* | |
C79 | 0.4734 (4) | 0.2731 (3) | 0.2185 (2) | 0.0253 (6) | |
H79A | 0.367420 | 0.233105 | 0.210725 | 0.030* | |
H79B | 0.481747 | 0.314594 | 0.166012 | 0.030* | |
C80 | 0.5637 (4) | 0.3857 (3) | 0.3178 (2) | 0.0262 (7) | |
H80A | 0.666999 | 0.433605 | 0.321884 | 0.031* | |
H80B | 0.520889 | 0.454931 | 0.323514 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0177 (3) | 0.0172 (3) | 0.0191 (4) | 0.0079 (3) | 0.0094 (3) | 0.0065 (3) |
P2 | 0.0171 (3) | 0.0172 (3) | 0.0191 (4) | 0.0075 (3) | 0.0086 (3) | 0.0052 (3) |
O1 | 0.0211 (10) | 0.0248 (10) | 0.0307 (12) | 0.0116 (8) | 0.0137 (9) | 0.0102 (9) |
O2 | 0.0166 (10) | 0.0260 (10) | 0.0271 (11) | 0.0094 (8) | 0.0100 (9) | 0.0066 (8) |
O3 | 0.0296 (11) | 0.0169 (9) | 0.0204 (10) | 0.0075 (8) | 0.0106 (9) | 0.0069 (8) |
O4 | 0.0264 (10) | 0.0177 (9) | 0.0216 (10) | 0.0080 (8) | 0.0112 (9) | 0.0075 (8) |
O5 | 0.0203 (10) | 0.0184 (10) | 0.0185 (10) | 0.0059 (8) | 0.0072 (8) | 0.0052 (8) |
O6 | 0.0294 (11) | 0.0246 (10) | 0.0250 (11) | 0.0153 (9) | 0.0177 (9) | 0.0116 (9) |
N1 | 0.0147 (11) | 0.0212 (12) | 0.0198 (12) | 0.0086 (9) | 0.0051 (10) | 0.0047 (9) |
N2 | 0.0152 (11) | 0.0238 (12) | 0.0183 (13) | 0.0090 (10) | 0.0061 (10) | 0.0018 (10) |
C1 | 0.0250 (14) | 0.0176 (13) | 0.0173 (14) | 0.0077 (11) | 0.0084 (12) | 0.0067 (11) |
C2 | 0.0204 (14) | 0.0300 (15) | 0.0221 (15) | 0.0094 (12) | 0.0103 (12) | 0.0106 (12) |
C3 | 0.0387 (17) | 0.0293 (16) | 0.0355 (17) | 0.0225 (14) | 0.0185 (15) | 0.0183 (13) |
C4 | 0.0380 (18) | 0.0260 (15) | 0.0398 (19) | 0.0109 (14) | 0.0183 (16) | 0.0178 (14) |
C5 | 0.0276 (16) | 0.0381 (18) | 0.045 (2) | 0.0118 (14) | 0.0199 (15) | 0.0244 (15) |
C6 | 0.0280 (16) | 0.0335 (17) | 0.0328 (17) | 0.0169 (13) | 0.0170 (14) | 0.0171 (14) |
C7 | 0.0230 (14) | 0.0226 (14) | 0.0295 (16) | 0.0138 (11) | 0.0162 (13) | 0.0140 (12) |
C8 | 0.0305 (15) | 0.0221 (14) | 0.0324 (17) | 0.0103 (12) | 0.0136 (14) | 0.0102 (13) |
C9 | 0.0376 (18) | 0.0250 (16) | 0.054 (2) | 0.0129 (14) | 0.0212 (17) | 0.0211 (15) |
C10 | 0.0331 (17) | 0.0364 (18) | 0.052 (2) | 0.0198 (14) | 0.0238 (16) | 0.0307 (16) |
C11 | 0.0286 (16) | 0.0454 (19) | 0.0320 (17) | 0.0209 (14) | 0.0134 (14) | 0.0214 (15) |
C12 | 0.0274 (16) | 0.0265 (15) | 0.0296 (17) | 0.0129 (12) | 0.0105 (13) | 0.0122 (12) |
C13 | 0.0193 (13) | 0.0171 (13) | 0.0184 (14) | 0.0026 (11) | 0.0050 (11) | 0.0034 (11) |
C14 | 0.0273 (15) | 0.0268 (15) | 0.0316 (16) | 0.0114 (12) | 0.0149 (13) | 0.0119 (12) |
C15 | 0.0395 (18) | 0.0286 (16) | 0.049 (2) | 0.0194 (14) | 0.0214 (17) | 0.0197 (15) |
C16 | 0.044 (2) | 0.0348 (18) | 0.045 (2) | 0.0165 (15) | 0.0231 (17) | 0.0269 (16) |
C17 | 0.0380 (18) | 0.0365 (18) | 0.0378 (19) | 0.0131 (15) | 0.0241 (16) | 0.0162 (14) |
C18 | 0.0263 (15) | 0.0258 (15) | 0.0312 (17) | 0.0102 (12) | 0.0136 (13) | 0.0095 (12) |
C19 | 0.0228 (14) | 0.0264 (15) | 0.0176 (14) | 0.0127 (12) | 0.0106 (12) | 0.0098 (11) |
C20 | 0.0279 (15) | 0.0261 (15) | 0.0278 (16) | 0.0089 (12) | 0.0122 (13) | 0.0125 (12) |
C21 | 0.0281 (16) | 0.0450 (19) | 0.0334 (18) | 0.0153 (14) | 0.0162 (14) | 0.0205 (15) |
C22 | 0.0337 (17) | 0.054 (2) | 0.0248 (16) | 0.0254 (16) | 0.0171 (14) | 0.0153 (15) |
C23 | 0.0305 (17) | 0.0387 (18) | 0.0246 (16) | 0.0137 (14) | 0.0081 (14) | 0.0000 (13) |
C24 | 0.0248 (15) | 0.0274 (16) | 0.0282 (17) | 0.0067 (13) | 0.0102 (13) | 0.0047 (13) |
C26 | 0.0266 (15) | 0.0182 (13) | 0.0229 (15) | 0.0085 (12) | 0.0119 (13) | 0.0072 (11) |
C27 | 0.0287 (16) | 0.0240 (14) | 0.0191 (15) | 0.0101 (12) | 0.0114 (13) | 0.0092 (12) |
C28 | 0.0176 (13) | 0.0207 (13) | 0.0158 (14) | 0.0097 (11) | 0.0050 (12) | 0.0038 (11) |
C29 | 0.0225 (15) | 0.0192 (13) | 0.0217 (15) | 0.0080 (11) | 0.0121 (12) | 0.0066 (11) |
C30 | 0.0227 (14) | 0.0206 (13) | 0.0175 (14) | 0.0092 (11) | 0.0110 (12) | 0.0073 (11) |
C32 | 0.0180 (13) | 0.0208 (14) | 0.0178 (14) | 0.0085 (11) | 0.0065 (12) | 0.0043 (11) |
P51 | 0.0151 (3) | 0.0249 (4) | 0.0223 (4) | 0.0076 (3) | 0.0072 (3) | 0.0044 (3) |
P52 | 0.0166 (3) | 0.0305 (4) | 0.0196 (4) | 0.0104 (3) | 0.0086 (3) | 0.0082 (3) |
O51 | 0.0185 (10) | 0.0399 (12) | 0.0267 (11) | 0.0142 (9) | 0.0084 (9) | 0.0086 (9) |
O52 | 0.0192 (10) | 0.0353 (12) | 0.0271 (11) | 0.0128 (9) | 0.0115 (9) | 0.0103 (9) |
O53 | 0.0225 (10) | 0.0226 (10) | 0.0258 (11) | 0.0058 (8) | 0.0069 (9) | 0.0060 (8) |
O54 | 0.0252 (10) | 0.0254 (11) | 0.0304 (12) | 0.0123 (9) | 0.0150 (9) | 0.0094 (9) |
O55 | 0.0282 (11) | 0.0504 (14) | 0.0277 (12) | 0.0224 (10) | 0.0146 (10) | 0.0183 (10) |
O56 | 0.0323 (12) | 0.0275 (11) | 0.0274 (12) | 0.0096 (9) | 0.0138 (10) | 0.0025 (9) |
N51 | 0.0135 (12) | 0.0325 (14) | 0.0257 (14) | 0.0059 (10) | 0.0067 (11) | 0.0001 (11) |
N52 | 0.0141 (11) | 0.0234 (12) | 0.0265 (14) | 0.0043 (10) | 0.0105 (11) | 0.0058 (10) |
C51 | 0.0236 (15) | 0.0243 (14) | 0.0310 (17) | 0.0095 (12) | 0.0155 (13) | 0.0100 (12) |
C52 | 0.0368 (18) | 0.0361 (18) | 0.0299 (18) | 0.0116 (15) | 0.0099 (15) | 0.0091 (14) |
C53 | 0.060 (2) | 0.046 (2) | 0.045 (2) | 0.0275 (18) | 0.030 (2) | 0.0273 (18) |
C54 | 0.063 (2) | 0.0303 (18) | 0.062 (3) | 0.0204 (17) | 0.043 (2) | 0.0210 (17) |
C55 | 0.062 (2) | 0.0265 (17) | 0.048 (2) | 0.0072 (16) | 0.029 (2) | 0.0058 (16) |
C56 | 0.0403 (19) | 0.0308 (17) | 0.0317 (18) | 0.0086 (14) | 0.0180 (15) | 0.0065 (14) |
C57 | 0.0224 (14) | 0.0263 (14) | 0.0272 (16) | 0.0140 (12) | 0.0122 (12) | 0.0133 (12) |
C58 | 0.0227 (15) | 0.0268 (15) | 0.0316 (18) | 0.0101 (12) | 0.0101 (14) | 0.0078 (13) |
C59 | 0.0321 (17) | 0.0324 (16) | 0.0294 (17) | 0.0168 (14) | 0.0123 (14) | 0.0118 (13) |
C60 | 0.0333 (17) | 0.0410 (18) | 0.0344 (18) | 0.0214 (14) | 0.0203 (15) | 0.0214 (14) |
C61 | 0.0269 (16) | 0.0405 (18) | 0.041 (2) | 0.0119 (14) | 0.0179 (15) | 0.0226 (15) |
C62 | 0.0252 (15) | 0.0265 (15) | 0.0305 (17) | 0.0056 (13) | 0.0081 (13) | 0.0097 (13) |
C63 | 0.0168 (13) | 0.0283 (15) | 0.0190 (14) | 0.0073 (11) | 0.0051 (11) | 0.0074 (11) |
C64 | 0.0277 (17) | 0.0321 (17) | 0.0323 (18) | 0.0105 (13) | 0.0136 (14) | 0.0071 (14) |
C65 | 0.0346 (19) | 0.046 (2) | 0.0300 (18) | 0.0130 (16) | 0.0116 (15) | 0.0036 (15) |
C66 | 0.0322 (18) | 0.054 (2) | 0.0297 (18) | 0.0084 (16) | 0.0102 (15) | 0.0137 (16) |
C67 | 0.0351 (18) | 0.049 (2) | 0.0334 (19) | 0.0102 (16) | 0.0113 (15) | 0.0250 (16) |
C68 | 0.0338 (18) | 0.0356 (18) | 0.0394 (19) | 0.0145 (15) | 0.0092 (15) | 0.0156 (15) |
C69 | 0.0331 (17) | 0.0197 (15) | 0.0433 (19) | 0.0135 (13) | 0.0195 (15) | 0.0084 (13) |
C70 | 0.039 (2) | 0.047 (2) | 0.077 (3) | 0.0283 (17) | 0.037 (2) | 0.033 (2) |
C71 | 0.055 (3) | 0.094 (4) | 0.125 (5) | 0.057 (3) | 0.056 (3) | 0.083 (4) |
C72 | 0.068 (3) | 0.100 (4) | 0.133 (5) | 0.061 (3) | 0.068 (3) | 0.100 (4) |
C73 | 0.052 (2) | 0.058 (2) | 0.099 (4) | 0.038 (2) | 0.052 (3) | 0.054 (3) |
C74 | 0.0324 (17) | 0.0338 (17) | 0.059 (2) | 0.0204 (14) | 0.0250 (17) | 0.0248 (16) |
C75 | 0.0161 (14) | 0.0244 (14) | 0.0230 (16) | 0.0074 (11) | 0.0093 (12) | 0.0033 (12) |
C76 | 0.0249 (15) | 0.0255 (14) | 0.0259 (16) | 0.0102 (12) | 0.0088 (13) | 0.0119 (12) |
C77 | 0.0248 (15) | 0.0192 (14) | 0.0288 (16) | 0.0088 (12) | 0.0110 (13) | 0.0105 (12) |
C78 | 0.0156 (13) | 0.0232 (14) | 0.0232 (16) | 0.0066 (11) | 0.0082 (12) | 0.0077 (12) |
C79 | 0.0292 (16) | 0.0234 (14) | 0.0274 (16) | 0.0142 (12) | 0.0097 (13) | 0.0114 (12) |
C80 | 0.0305 (17) | 0.0239 (15) | 0.0292 (17) | 0.0161 (13) | 0.0114 (14) | 0.0094 (13) |
Geometric parameters (Å, º) top
P1—O1 | 1.463 (2) | P51—O51 | 1.466 (2) |
P1—O3 | 1.590 (2) | P51—O53 | 1.585 (2) |
P1—O4 | 1.5937 (19) | P51—O54 | 1.590 (2) |
P1—N1 | 1.609 (2) | P51—N51 | 1.603 (3) |
P2—O2 | 1.468 (2) | P52—O52 | 1.468 (2) |
P2—O6 | 1.580 (2) | P52—O56 | 1.586 (2) |
P2—O5 | 1.5900 (19) | P52—O55 | 1.593 (2) |
P2—N2 | 1.602 (2) | P52—N52 | 1.595 (3) |
O3—C1 | 1.415 (3) | O53—C51 | 1.398 (3) |
O4—C7 | 1.407 (3) | O54—C57 | 1.405 (4) |
O5—C13 | 1.406 (3) | O55—C63 | 1.397 (4) |
O6—C19 | 1.411 (3) | O56—C69 | 1.404 (4) |
N1—C32 | 1.473 (4) | N51—C75 | 1.467 (4) |
N1—H1N | 0.85 (2) | N51—H51N | 0.87 (2) |
N2—C28 | 1.464 (3) | N52—C78 | 1.468 (4) |
N2—H2N | 0.85 (2) | N52—H52N | 0.84 (2) |
C1—C2 | 1.375 (4) | C51—C56 | 1.368 (4) |
C1—C6 | 1.378 (4) | C51—C52 | 1.380 (5) |
C2—C3 | 1.385 (4) | C52—C53 | 1.390 (5) |
C2—H2C | 0.9500 | C52—H52C | 0.9500 |
C3—C4 | 1.390 (5) | C53—C54 | 1.378 (6) |
C3—H3A | 0.9500 | C53—H53A | 0.9500 |
C4—C5 | 1.379 (5) | C54—C55 | 1.378 (6) |
C4—H4A | 0.9500 | C54—H54A | 0.9500 |
C5—C6 | 1.387 (4) | C55—C56 | 1.389 (5) |
C5—H5A | 0.9500 | C55—H55A | 0.9500 |
C6—H6A | 0.9500 | C56—H56A | 0.9500 |
C7—C12 | 1.375 (4) | C57—C58 | 1.378 (4) |
C7—C8 | 1.385 (4) | C57—C62 | 1.381 (4) |
C8—C9 | 1.393 (4) | C58—C59 | 1.380 (5) |
C8—H8A | 0.9500 | C58—H58A | 0.9500 |
C9—C10 | 1.375 (5) | C59—C60 | 1.389 (5) |
C9—H9A | 0.9500 | C59—H59A | 0.9500 |
C10—C11 | 1.382 (5) | C60—C61 | 1.375 (5) |
C10—H10A | 0.9500 | C60—H60A | 0.9500 |
C11—C12 | 1.390 (4) | C61—C62 | 1.381 (5) |
C11—H11A | 0.9500 | C61—H61A | 0.9500 |
C12—H12A | 0.9500 | C62—H62A | 0.9500 |
C13—C14 | 1.381 (4) | C63—C64 | 1.373 (5) |
C13—C18 | 1.382 (4) | C63—C68 | 1.388 (5) |
C14—C15 | 1.382 (4) | C64—C65 | 1.387 (5) |
C14—H14A | 0.9500 | C64—H64A | 0.9500 |
C15—C16 | 1.385 (5) | C65—C66 | 1.372 (6) |
C15—H15A | 0.9500 | C65—H65A | 0.9500 |
C16—C17 | 1.389 (5) | C66—C67 | 1.379 (6) |
C16—H16A | 0.9500 | C66—H66A | 0.9500 |
C17—C18 | 1.382 (5) | C67—C68 | 1.400 (5) |
C17—H17A | 0.9500 | C67—H67A | 0.9500 |
C18—H18A | 0.9500 | C68—H68A | 0.9500 |
C19—C24 | 1.375 (4) | C69—C70 | 1.371 (5) |
C19—C20 | 1.383 (4) | C69—C74 | 1.384 (5) |
C20—C21 | 1.385 (4) | C70—C71 | 1.375 (6) |
C20—H20A | 0.9500 | C70—H70A | 0.9500 |
C21—C22 | 1.373 (5) | C71—C72 | 1.393 (6) |
C21—H21A | 0.9500 | C71—H71A | 0.9500 |
C22—C23 | 1.389 (5) | C72—C73 | 1.372 (6) |
C22—H22A | 0.9500 | C72—H72A | 0.9500 |
C23—C24 | 1.381 (5) | C73—C74 | 1.375 (5) |
C23—H23A | 0.9500 | C73—H73A | 0.9500 |
C24—H24A | 0.9500 | C74—H74A | 0.9500 |
C26—C27 | 1.523 (4) | C75—C76 | 1.523 (4) |
C26—C32 | 1.524 (4) | C75—C80 | 1.523 (4) |
C26—H26A | 0.9900 | C75—H75A | 1.0000 |
C26—H26B | 0.9900 | C76—C77 | 1.528 (4) |
C27—C28 | 1.522 (4) | C76—H76A | 0.9900 |
C27—H27A | 0.9900 | C76—H76B | 0.9900 |
C27—H27B | 0.9900 | C77—C78 | 1.518 (4) |
C28—C29 | 1.520 (4) | C77—H77A | 0.9900 |
C28—H28A | 1.0000 | C77—H77B | 0.9900 |
C29—C30 | 1.525 (4) | C78—C79 | 1.518 (4) |
C29—H29A | 0.9900 | C78—H78A | 1.0000 |
C29—H29B | 0.9900 | C79—C80 | 1.533 (4) |
C30—C32 | 1.529 (4) | C79—H79A | 0.9900 |
C30—H30A | 0.9900 | C79—H79B | 0.9900 |
C30—H30B | 0.9900 | C80—H80A | 0.9900 |
C32—H32A | 1.0000 | C80—H80B | 0.9900 |
| | | |
O1—P1—O3 | 115.74 (12) | O51—P51—O53 | 115.32 (12) |
O1—P1—O4 | 114.34 (12) | O51—P51—O54 | 112.46 (12) |
O3—P1—O4 | 94.73 (10) | O53—P51—O54 | 100.97 (11) |
O1—P1—N1 | 113.23 (12) | O51—P51—N51 | 116.36 (14) |
O3—P1—N1 | 109.01 (12) | O53—P51—N51 | 104.92 (12) |
O4—P1—N1 | 108.18 (12) | O54—P51—N51 | 105.21 (13) |
O2—P2—O6 | 113.89 (12) | O52—P52—O56 | 114.91 (13) |
O2—P2—O5 | 115.07 (12) | O52—P52—O55 | 113.48 (12) |
O6—P2—O5 | 100.23 (11) | O56—P52—O55 | 100.21 (13) |
O2—P2—N2 | 114.21 (13) | O52—P52—N52 | 114.76 (12) |
O6—P2—N2 | 106.65 (12) | O56—P52—N52 | 107.10 (12) |
O5—P2—N2 | 105.44 (11) | O55—P52—N52 | 104.95 (13) |
C1—O3—P1 | 116.03 (17) | C51—O53—P51 | 126.20 (19) |
C7—O4—P1 | 123.86 (18) | C57—O54—P51 | 121.73 (19) |
C13—O5—P2 | 118.23 (17) | C63—O55—P52 | 123.82 (19) |
C19—O6—P2 | 122.84 (18) | C69—O56—P52 | 119.24 (19) |
C32—N1—P1 | 124.40 (19) | C75—N51—P51 | 123.7 (2) |
C32—N1—H1N | 113 (2) | C75—N51—H51N | 119 (2) |
P1—N1—H1N | 119 (2) | P51—N51—H51N | 116 (2) |
C28—N2—P2 | 124.3 (2) | C78—N52—P52 | 125.6 (2) |
C28—N2—H2N | 115 (2) | C78—N52—H52N | 114 (2) |
P2—N2—H2N | 118 (2) | P52—N52—H52N | 120 (2) |
C2—C1—C6 | 122.0 (3) | C56—C51—C52 | 121.5 (3) |
C2—C1—O3 | 118.5 (2) | C56—C51—O53 | 115.1 (3) |
C6—C1—O3 | 119.5 (3) | C52—C51—O53 | 123.5 (3) |
C1—C2—C3 | 119.0 (3) | C51—C52—C53 | 118.8 (3) |
C1—C2—H2C | 120.5 | C51—C52—H52C | 120.6 |
C3—C2—H2C | 120.5 | C53—C52—H52C | 120.6 |
C2—C3—C4 | 120.0 (3) | C54—C53—C52 | 120.4 (4) |
C2—C3—H3A | 120.0 | C54—C53—H53A | 119.8 |
C4—C3—H3A | 120.0 | C52—C53—H53A | 119.8 |
C5—C4—C3 | 119.9 (3) | C55—C54—C53 | 119.7 (3) |
C5—C4—H4A | 120.0 | C55—C54—H54A | 120.1 |
C3—C4—H4A | 120.0 | C53—C54—H54A | 120.1 |
C4—C5—C6 | 120.5 (3) | C54—C55—C56 | 120.4 (3) |
C4—C5—H5A | 119.8 | C54—C55—H55A | 119.8 |
C6—C5—H5A | 119.8 | C56—C55—H55A | 119.8 |
C1—C6—C5 | 118.6 (3) | C51—C56—C55 | 119.2 (3) |
C1—C6—H6A | 120.7 | C51—C56—H56A | 120.4 |
C5—C6—H6A | 120.7 | C55—C56—H56A | 120.4 |
C12—C7—C8 | 121.7 (3) | C58—C57—C62 | 121.3 (3) |
C12—C7—O4 | 123.8 (3) | C58—C57—O54 | 120.4 (3) |
C8—C7—O4 | 114.5 (3) | C62—C57—O54 | 118.1 (3) |
C7—C8—C9 | 118.5 (3) | C57—C58—C59 | 119.0 (3) |
C7—C8—H8A | 120.8 | C57—C58—H58A | 120.5 |
C9—C8—H8A | 120.8 | C59—C58—H58A | 120.5 |
C10—C9—C8 | 120.5 (3) | C58—C59—C60 | 120.6 (3) |
C10—C9—H9A | 119.7 | C58—C59—H59A | 119.7 |
C8—C9—H9A | 119.7 | C60—C59—H59A | 119.7 |
C9—C10—C11 | 120.1 (3) | C61—C60—C59 | 119.3 (3) |
C9—C10—H10A | 119.9 | C61—C60—H60A | 120.4 |
C11—C10—H10A | 119.9 | C59—C60—H60A | 120.4 |
C10—C11—C12 | 120.2 (3) | C60—C61—C62 | 121.0 (3) |
C10—C11—H11A | 119.9 | C60—C61—H61A | 119.5 |
C12—C11—H11A | 119.9 | C62—C61—H61A | 119.5 |
C7—C12—C11 | 118.9 (3) | C57—C62—C61 | 118.8 (3) |
C7—C12—H12A | 120.5 | C57—C62—H62A | 120.6 |
C11—C12—H12A | 120.5 | C61—C62—H62A | 120.6 |
C14—C13—C18 | 122.3 (3) | C64—C63—C68 | 120.6 (3) |
C14—C13—O5 | 118.3 (3) | C64—C63—O55 | 122.0 (3) |
C18—C13—O5 | 119.4 (3) | C68—C63—O55 | 117.4 (3) |
C13—C14—C15 | 118.3 (3) | C63—C64—C65 | 120.7 (3) |
C13—C14—H14A | 120.8 | C63—C64—H64A | 119.7 |
C15—C14—H14A | 120.8 | C65—C64—H64A | 119.7 |
C14—C15—C16 | 120.7 (3) | C66—C65—C64 | 118.7 (4) |
C14—C15—H15A | 119.6 | C66—C65—H65A | 120.6 |
C16—C15—H15A | 119.6 | C64—C65—H65A | 120.6 |
C15—C16—C17 | 119.7 (3) | C65—C66—C67 | 121.8 (3) |
C15—C16—H16A | 120.1 | C65—C66—H66A | 119.1 |
C17—C16—H16A | 120.1 | C67—C66—H66A | 119.1 |
C18—C17—C16 | 120.5 (3) | C66—C67—C68 | 119.2 (3) |
C18—C17—H17A | 119.8 | C66—C67—H67A | 120.4 |
C16—C17—H17A | 119.8 | C68—C67—H67A | 120.4 |
C13—C18—C17 | 118.5 (3) | C63—C68—C67 | 119.0 (3) |
C13—C18—H18A | 120.8 | C63—C68—H68A | 120.5 |
C17—C18—H18A | 120.8 | C67—C68—H68A | 120.5 |
C24—C19—C20 | 121.9 (3) | C70—C69—C74 | 121.1 (3) |
C24—C19—O6 | 120.8 (2) | C70—C69—O56 | 121.0 (3) |
C20—C19—O6 | 117.2 (2) | C74—C69—O56 | 117.8 (3) |
C19—C20—C21 | 118.4 (3) | C69—C70—C71 | 119.4 (3) |
C19—C20—H20A | 120.8 | C69—C70—H70A | 120.3 |
C21—C20—H20A | 120.8 | C71—C70—H70A | 120.3 |
C22—C21—C20 | 120.7 (3) | C70—C71—C72 | 119.9 (4) |
C22—C21—H21A | 119.6 | C70—C71—H71A | 120.1 |
C20—C21—H21A | 119.6 | C72—C71—H71A | 120.1 |
C21—C22—C23 | 119.9 (3) | C73—C72—C71 | 120.1 (4) |
C21—C22—H22A | 120.1 | C73—C72—H72A | 120.0 |
C23—C22—H22A | 120.1 | C71—C72—H72A | 120.0 |
C24—C23—C22 | 120.3 (3) | C72—C73—C74 | 120.2 (4) |
C24—C23—H23A | 119.9 | C72—C73—H73A | 119.9 |
C22—C23—H23A | 119.9 | C74—C73—H73A | 119.9 |
C19—C24—C23 | 118.8 (3) | C73—C74—C69 | 119.2 (3) |
C19—C24—H24A | 120.6 | C73—C74—H74A | 120.4 |
C23—C24—H24A | 120.6 | C69—C74—H74A | 120.4 |
C27—C26—C32 | 111.1 (2) | N51—C75—C76 | 110.4 (2) |
C27—C26—H26A | 109.4 | N51—C75—C80 | 110.1 (2) |
C32—C26—H26A | 109.4 | C76—C75—C80 | 110.9 (2) |
C27—C26—H26B | 109.4 | N51—C75—H75A | 108.4 |
C32—C26—H26B | 109.4 | C76—C75—H75A | 108.4 |
H26A—C26—H26B | 108.0 | C80—C75—H75A | 108.4 |
C28—C27—C26 | 111.2 (2) | C75—C76—C77 | 111.7 (2) |
C28—C27—H27A | 109.4 | C75—C76—H76A | 109.3 |
C26—C27—H27A | 109.4 | C77—C76—H76A | 109.3 |
C28—C27—H27B | 109.4 | C75—C76—H76B | 109.3 |
C26—C27—H27B | 109.4 | C77—C76—H76B | 109.3 |
H27A—C27—H27B | 108.0 | H76A—C76—H76B | 108.0 |
N2—C28—C29 | 109.6 (2) | C78—C77—C76 | 111.8 (2) |
N2—C28—C27 | 112.2 (2) | C78—C77—H77A | 109.3 |
C29—C28—C27 | 110.8 (2) | C76—C77—H77A | 109.3 |
N2—C28—H28A | 108.0 | C78—C77—H77B | 109.3 |
C29—C28—H28A | 108.0 | C76—C77—H77B | 109.3 |
C27—C28—H28A | 108.0 | H77A—C77—H77B | 107.9 |
C28—C29—C30 | 111.6 (2) | N52—C78—C79 | 110.2 (2) |
C28—C29—H29A | 109.3 | N52—C78—C77 | 110.6 (2) |
C30—C29—H29A | 109.3 | C79—C78—C77 | 111.2 (3) |
C28—C29—H29B | 109.3 | N52—C78—H78A | 108.2 |
C30—C29—H29B | 109.3 | C79—C78—H78A | 108.2 |
H29A—C29—H29B | 108.0 | C77—C78—H78A | 108.2 |
C29—C30—C32 | 111.8 (2) | C78—C79—C80 | 111.1 (3) |
C29—C30—H30A | 109.3 | C78—C79—H79A | 109.4 |
C32—C30—H30A | 109.3 | C80—C79—H79A | 109.4 |
C29—C30—H30B | 109.3 | C78—C79—H79B | 109.4 |
C32—C30—H30B | 109.3 | C80—C79—H79B | 109.4 |
H30A—C30—H30B | 107.9 | H79A—C79—H79B | 108.0 |
N1—C32—C26 | 109.4 (2) | C75—C80—C79 | 112.2 (2) |
N1—C32—C30 | 110.6 (2) | C75—C80—H80A | 109.2 |
C26—C32—C30 | 111.2 (2) | C79—C80—H80A | 109.2 |
N1—C32—H32A | 108.5 | C75—C80—H80B | 109.2 |
C26—C32—H32A | 108.5 | C79—C80—H80B | 109.2 |
C30—C32—H32A | 108.5 | H80A—C80—H80B | 107.9 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O52i | 0.85 (2) | 2.03 (2) | 2.863 (3) | 167 (3) |
N2—H2N···O51 | 0.85 (2) | 2.00 (2) | 2.820 (3) | 162 (3) |
N51—H51N···O2ii | 0.87 (2) | 1.98 (3) | 2.802 (3) | 158 (3) |
N52—H52N···O1 | 0.84 (2) | 2.04 (2) | 2.866 (3) | 168 (3) |
C22—H22A···O4iii | 0.95 | 2.51 | 3.418 (4) | 160 |
C6—H6A···O55 | 0.95 | 2.69 | 3.565 (4) | 154 |
C74—H74A···O1 | 0.95 | 2.61 | 3.329 (4) | 133 |
C2—H2C···O52i | 0.95 | 2.69 | 3.465 (3) | 139 |
C2—H2C···CG1i | 0.95 | 2.92 | 3.593 (8) | 129 |
Symmetry codes: (i) x−1, 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
C10H18N2O4P2S2 | F(000) = 744 |
Mr = 356.32 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 13.2517 (3) Å | Cell parameters from 6840 reflections |
b = 10.0091 (2) Å | θ = 3.1–28.0° |
c = 13.9580 (3) Å | µ = 0.51 mm−1 |
β = 112.9309 (12)° | T = 295 K |
V = 1705.05 (6) Å3 | Block, colourless |
Z = 4 | 0.43 × 0.36 × 0.31 mm |
Data collection top
Nonius KappaCCD diffractometer | 3267 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
φ scans and ω scans | θmax = 28.0°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −17→17 |
Tmin = 0.790, Tmax = 0.845 | k = −12→13 |
6840 measured reflections | l = −18→18 |
4091 independent reflections | |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H 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 reflections | Δρmax = 0.70 e Å−3 |
191 parameters | Δρmin = −0.48 e Å−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 | x | y | z | Uiso*/Ueq | |
C1 | −0.10510 (16) | 0.22673 (18) | 0.16416 (14) | 0.0383 (4) | |
C2 | −0.05330 (16) | 0.33804 (19) | 0.22145 (15) | 0.0406 (4) | |
H2 | −0.080489 | 0.422741 | 0.197783 | 0.049* | |
C3 | 0.03820 (16) | 0.3252 (2) | 0.31329 (15) | 0.0432 (5) | |
H3 | 0.071866 | 0.400946 | 0.350764 | 0.052* | |
C4 | 0.07964 (16) | 0.19929 (19) | 0.34936 (15) | 0.0401 (4) | |
C5 | 0.03004 (16) | 0.0882 (2) | 0.29087 (15) | 0.0442 (5) | |
H5 | 0.058510 | 0.003716 | 0.313678 | 0.053* | |
C6 | −0.06154 (17) | 0.10094 (19) | 0.19870 (15) | 0.0441 (5) | |
H6 | −0.093740 | 0.025412 | 0.160088 | 0.053* | |
N1 | −0.19948 (15) | 0.24601 (16) | 0.07154 (14) | 0.0491 (5) | |
H1N | −0.218 (2) | 0.3233 (18) | 0.060 (2) | 0.059* | |
P1 | −0.27879 (4) | 0.13688 (5) | −0.00992 (4) | 0.03875 (14) | |
S1 | −0.39878 (5) | 0.22087 (6) | −0.11912 (5) | 0.05876 (19) | |
O1 | −0.20470 (13) | 0.04058 (16) | −0.04448 (12) | 0.0535 (4) | |
C7 | −0.1410 (3) | 0.0939 (5) | −0.0986 (3) | 0.1061 (13) | |
H7A | −0.185412 | 0.153669 | −0.152217 | 0.159* | |
H7B | −0.115829 | 0.022073 | −0.129260 | 0.159* | |
H7C | −0.079075 | 0.141495 | −0.050487 | 0.159* | |
O2 | −0.30821 (13) | 0.02609 (16) | 0.05507 (12) | 0.0553 (4) | |
C8 | −0.3725 (3) | 0.0616 (4) | 0.1146 (3) | 0.0930 (11) | |
H8A | −0.335379 | 0.130267 | 0.163726 | 0.140* | |
H8B | −0.381900 | −0.015587 | 0.151065 | 0.140* | |
H8C | −0.442969 | 0.093827 | 0.068415 | 0.140* | |
N2 | 0.17100 (16) | 0.18068 (18) | 0.44518 (14) | 0.0541 (5) | |
H2N | 0.188 (2) | 0.0995 (18) | 0.460 (2) | 0.065* | |
P2 | 0.24331 (4) | 0.28916 (5) | 0.53117 (4) | 0.04238 (15) | |
S2 | 0.35199 (5) | 0.20676 (7) | 0.65024 (5) | 0.0634 (2) | |
O3 | 0.28520 (14) | 0.39623 (18) | 0.47204 (13) | 0.0635 (4) | |
C9 | 0.3563 (4) | 0.3603 (6) | 0.4224 (3) | 0.1276 (17) | |
H9A | 0.427943 | 0.341952 | 0.474035 | 0.191* | |
H9B | 0.360601 | 0.432479 | 0.378888 | 0.191* | |
H9C | 0.328474 | 0.282030 | 0.380640 | 0.191* | |
O4 | 0.16411 (17) | 0.3914 (2) | 0.55171 (14) | 0.0803 (6) | |
C10 | 0.1129 (4) | 0.3727 (6) | 0.6169 (4) | 0.152 (2) | |
H10A | 0.147202 | 0.300551 | 0.663516 | 0.228* | |
H10B | 0.037320 | 0.351315 | 0.577502 | 0.228* | |
H10C | 0.117510 | 0.452852 | 0.656121 | 0.228* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0372 (10) | 0.0324 (9) | 0.0343 (9) | −0.0009 (7) | 0.0021 (8) | −0.0010 (7) |
C2 | 0.0435 (10) | 0.0282 (8) | 0.0395 (10) | 0.0019 (8) | 0.0046 (8) | 0.0011 (8) |
C3 | 0.0459 (11) | 0.0317 (9) | 0.0397 (10) | −0.0028 (8) | 0.0033 (8) | −0.0040 (8) |
C4 | 0.0369 (10) | 0.0365 (9) | 0.0345 (9) | 0.0010 (8) | 0.0005 (8) | 0.0003 (8) |
C5 | 0.0461 (11) | 0.0307 (9) | 0.0426 (10) | 0.0051 (8) | 0.0027 (8) | 0.0010 (8) |
C6 | 0.0472 (11) | 0.0305 (9) | 0.0401 (10) | 0.0007 (8) | 0.0012 (8) | −0.0040 (8) |
N1 | 0.0479 (10) | 0.0277 (8) | 0.0458 (9) | 0.0019 (7) | −0.0100 (8) | −0.0005 (7) |
P1 | 0.0376 (3) | 0.0323 (3) | 0.0363 (3) | −0.00116 (19) | 0.0034 (2) | −0.0027 (2) |
S1 | 0.0486 (3) | 0.0500 (3) | 0.0506 (3) | 0.0034 (2) | −0.0103 (2) | −0.0014 (3) |
O1 | 0.0531 (9) | 0.0547 (9) | 0.0502 (8) | 0.0068 (7) | 0.0172 (7) | −0.0068 (7) |
C7 | 0.094 (2) | 0.145 (3) | 0.104 (3) | 0.021 (2) | 0.065 (2) | 0.021 (3) |
O2 | 0.0567 (9) | 0.0503 (9) | 0.0557 (9) | −0.0091 (7) | 0.0183 (7) | 0.0048 (7) |
C8 | 0.092 (2) | 0.125 (3) | 0.0770 (19) | −0.020 (2) | 0.0494 (18) | 0.000 (2) |
N2 | 0.0529 (11) | 0.0343 (9) | 0.0469 (10) | 0.0037 (8) | −0.0114 (8) | −0.0006 (8) |
P2 | 0.0421 (3) | 0.0426 (3) | 0.0335 (3) | 0.0027 (2) | 0.0050 (2) | −0.0046 (2) |
S2 | 0.0600 (4) | 0.0617 (4) | 0.0421 (3) | 0.0054 (3) | −0.0089 (3) | −0.0022 (3) |
O3 | 0.0650 (10) | 0.0615 (10) | 0.0548 (9) | −0.0133 (9) | 0.0134 (8) | 0.0006 (8) |
C9 | 0.111 (3) | 0.191 (5) | 0.108 (3) | −0.007 (3) | 0.073 (3) | 0.016 (3) |
O4 | 0.0843 (13) | 0.0981 (15) | 0.0541 (10) | 0.0405 (12) | 0.0220 (9) | −0.0052 (10) |
C10 | 0.128 (4) | 0.238 (6) | 0.122 (3) | 0.063 (4) | 0.085 (3) | 0.007 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.387 (3) | C7—H7B | 0.9600 |
C1—C6 | 1.391 (3) | C7—H7C | 0.9600 |
C1—N1 | 1.419 (2) | O2—C8 | 1.447 (3) |
C2—C3 | 1.385 (3) | C8—H8A | 0.9600 |
C2—H2 | 0.9300 | C8—H8B | 0.9600 |
C3—C4 | 1.389 (3) | C8—H8C | 0.9600 |
C3—H3 | 0.9300 | N2—P2 | 1.6253 (18) |
C4—C5 | 1.385 (3) | N2—H2N | 0.847 (17) |
C4—N2 | 1.424 (2) | P2—O4 | 1.5702 (18) |
C5—C6 | 1.388 (3) | P2—O3 | 1.5794 (18) |
C5—H5 | 0.9300 | P2—S2 | 1.9109 (8) |
C6—H6 | 0.9300 | O3—C9 | 1.416 (4) |
N1—P1 | 1.6307 (17) | C9—H9A | 0.9600 |
N1—H1N | 0.807 (16) | C9—H9B | 0.9600 |
P1—O2 | 1.5749 (16) | C9—H9C | 0.9600 |
P1—O1 | 1.5795 (16) | O4—C10 | 1.343 (4) |
P1—S1 | 1.9156 (7) | C10—H10A | 0.9600 |
O1—C7 | 1.437 (3) | C10—H10B | 0.9600 |
C7—H7A | 0.9600 | C10—H10C | 0.9600 |
| | | |
C2—C1—C6 | 118.81 (17) | H7A—C7—H7C | 109.5 |
C2—C1—N1 | 118.59 (17) | H7B—C7—H7C | 109.5 |
C6—C1—N1 | 122.59 (17) | C8—O2—P1 | 119.39 (19) |
C3—C2—C1 | 121.15 (18) | O2—C8—H8A | 109.5 |
C3—C2—H2 | 119.4 | O2—C8—H8B | 109.5 |
C1—C2—H2 | 119.4 | H8A—C8—H8B | 109.5 |
C2—C3—C4 | 119.95 (18) | O2—C8—H8C | 109.5 |
C2—C3—H3 | 120.0 | H8A—C8—H8C | 109.5 |
C4—C3—H3 | 120.0 | H8B—C8—H8C | 109.5 |
C5—C4—C3 | 119.05 (17) | C4—N2—P2 | 130.33 (15) |
C5—C4—N2 | 118.90 (17) | C4—N2—H2N | 113.7 (19) |
C3—C4—N2 | 122.05 (17) | P2—N2—H2N | 115.9 (18) |
C4—C5—C6 | 121.01 (18) | O4—P2—O3 | 92.82 (12) |
C4—C5—H5 | 119.5 | O4—P2—N2 | 109.06 (11) |
C6—C5—H5 | 119.5 | O3—P2—N2 | 107.07 (10) |
C5—C6—C1 | 119.96 (18) | O4—P2—S2 | 116.96 (8) |
C5—C6—H6 | 120.0 | O3—P2—S2 | 116.63 (7) |
C1—C6—H6 | 120.0 | N2—P2—S2 | 112.43 (7) |
C1—N1—P1 | 130.09 (14) | C9—O3—P2 | 121.3 (3) |
C1—N1—H1N | 113.4 (19) | O3—C9—H9A | 109.5 |
P1—N1—H1N | 116.4 (19) | O3—C9—H9B | 109.5 |
O2—P1—O1 | 93.96 (9) | H9A—C9—H9B | 109.5 |
O2—P1—N1 | 107.88 (10) | O3—C9—H9C | 109.5 |
O1—P1—N1 | 108.26 (10) | H9A—C9—H9C | 109.5 |
O2—P1—S1 | 116.89 (7) | H9B—C9—H9C | 109.5 |
O1—P1—S1 | 116.54 (7) | C10—O4—P2 | 125.7 (3) |
N1—P1—S1 | 111.75 (7) | O4—C10—H10A | 109.5 |
C7—O1—P1 | 119.8 (2) | O4—C10—H10B | 109.5 |
O1—C7—H7A | 109.5 | H10A—C10—H10B | 109.5 |
O1—C7—H7B | 109.5 | O4—C10—H10C | 109.5 |
H7A—C7—H7B | 109.5 | H10A—C10—H10C | 109.5 |
O1—C7—H7C | 109.5 | H10B—C10—H10C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O3 | 0.93 | 2.67 | 3.237 (2) | 120 |
C3—H3···O4 | 0.93 | 2.59 | 3.158 (3) | 120 |
N1—H1N···O1i | 0.81 (2) | 2.38 (2) | 3.174 (2) | 169 (2) |
N2—H2N···O3ii | 0.85 (2) | 2.22 (2) | 3.042 (3) | 165 (2) |
Symmetry codes: (i) −x−1/2, y+1/2, −z; (ii) −x+1/2, y−1/2, −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) topCompound (I) | | | | | |
Segment | Bond angles (°) | BD(P-O) | Contribution portions (%) | BD(C-O) | Contribution portions (%) |
P1O3C1 | 125.0815 | BD(P1-O3) | s (26.17), p (73.79) | BD(O3-C1) | s (37.13), p (62.81) |
P1O4C7 | 124.7019 | BD(P1-O4 | s (27.14), p (72.82) | BD(O4-C7) | s (37.20), p (62.75) |
P2O5C13 | 125.0868 | BD(P2-O5) | s (28.18), p (71.78) | BD(O5-C13) | s (37.94), p (62.01) |
P2O6C19 | 122.9743 | BD(P2-O6) | s (27.10), p (72.85) | BD(O6-C19) | s (37.33), p (62.62) |
P51O53C51 | 125.6914 | BD(P51-O53) | s (27.28), p (72.67) | BD(O53-C51) | s (37.88), p (62.07) |
P51O54C57 | 124.4525 | BD(P51-O54) | s (25.76), p (74.19) | BD(O54-C57) | s (36.49), p (63.45) |
P52O55C63 | 124.3808 | BD(P52-O56) | s (26.58), p (73.38) | BD(O55-C63) | s (36.89), p (63.0 6) |
P52O56C69 | 124.7025 | BD(P52-O55) | s (26.48), p (73.47) | BD(O56-C69) | s (37.31), p (62.63) |
| | | | | |
Compound (II) | | | | | |
Segment | Bond angles (?) | BD(P-O) | Contribution portions (%) | BD(C-O) | Contribution portions (%) |
P1O1C7 | 120.6189 | BDP1-O1 | s (28.60), p (71.35) | BD(O1-C7) | s (30.69), p (69.25) |
P1O2C8 | 120.5541 | BDP1-O2 | s (28.58), p (71.37) | BD(O2-C8) | s (30.67), p (69.28) |
P2O3C9 | 120.5650 | BDP2-O3 | s (28.58), p (71.37) | BD(O3-C9) | s (30.67), p (69.27) |
P2O4C10 | 120.6046 | BDP2-O4 | s (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 O | Contribution portions (%) | π O | Contribution portions (%) |
LP O3 | s (32.03), p (67.94) | π O3 | s (4.65), p (95.32) |
LP O4 | s (32.68), p (67.29) | π O4 | s (2.97), p (96.99) |
LP O5 | s (32.33), p (67.64) | π O5 | s (1.54), p (98.42) |
LP O6 | s (31.53), p (68.43) | π O6 | s (4.01), p (95.95) |
LP O53 | s (32.53), p (67.44) | π O53 | s (2.30), p (97.67) |
LP O54 | s (32.98), p (66.99) | π O54 | s (4.75), p (95.22) |
LP O55 | s (32.98), p (66.98) | π O55 | s (3.53), p (96.43) |
LP O56 | s (32.23), p (67.74) | π O56 | s (3.95), p (96.01) |
| | | |
(II) | | | |
LP O1 | s (40.54), p (59.43) | π O1 | s (0.15), p (99.81) |
LP O2 | s (40.56), p (59.41) | π O2 | s (0.18), p (99.78) |
LP O3 | s (40.55), p (59.41) | π O3 | s (0.17), p (99.79) |
LP O4 | s (40.54), p (59.42) | π O4 | s (0.16), p (99.80) |
NBO analysis results of (I) at the B3LYP/6-311g(d,p) method topDonor | Occu. No | E (a.u.) | Acceptor | Occu. No | E (a.u.) | E(2) (kcal mol-1) |
LP O52 | 1.9660 | -0.7549 | BD*(1) N1—H1N | 0.0287 | 0.4623 | 7.09 |
LP O51 | 1.9662 | -0.7572 | BD*(1) N2—H2N | 0.0287 | 0.4642 | 7.03 |
LP O1 | 1.9638 | -0.7389 | BD*(1) N52—H52N | 0.0325 | 0.4729 | 8.60 |
LP O2 | 1.9656 | -0.7430 | BD*(1) N51—H51N | 0.0303 | 0.4676 | 7.33 |
NBO analysis results of (II) at the B3LYP/6-311g(d,p) method topDonor | Occu. No | E (a.u.) | Acceptor | Occu. No | E (a.u.) | E(2) (kcal mol-1) |
LP O1 | 1.94905 | -0.65940 | BD*(1) N1—H1N | 0.02426 | 0.42790 | 4.88 |
LP O3 | 1.94410 | -0.65654 | BD*(1) N2—H2N | 0.03007 | 0.42825 | 8.16 |
NBO analysis results of (I) at the B3LYP/6-311g(d,p) method (optimization
is with restriction) topDonor | Occu. No | E (a.u.) | Acceptor | Occu. No | E (a.u.) | E(2) (kcal mol-1) |
LP O51 | 1.9556 | -0.8519 | BD*(1) N1—H1N | 0.0422 | 0.4557 | 12.86 |
LP O52 | 1.9544 | -0.8285 | BD*(1) N2—H2N | 0.0455 | 0.4672 | 13.87 |
LP O1 | 1.9567 | -0.8287 | BD*(1) N52—H52N | 0.0427 | 0.4672 | 13.41 |
LP O2 | 1.9536 | -0.8534 | BD*(1) N51—H51N | 0.0486 | 0.4517 | 14.21 |
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