Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112008566/fa3268sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270112008566/fa3268Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270112008566/fa3268IIsup3.hkl |
CCDC references: 879442; 879443
[(CH3)2N]P(O)Cl2 was prepared according to the literature method of Gholivand et al. (2002).
For the preparation of (I), a solution of tert-butylamine (2.7 g, 37.04 mmol) in chloroform (10 ml) was added at 273 K to a solution of [(CH3)2N]P(O)Cl2 (1.5 g, 9.26 mmol) in dry chloroform (15 ml). After stirring for 4 h, the solvent was removed [in vacuo? by heating?], and the product was washed with deionized water and recrystallized from chloroform–methanol (4:1 v/v) at room temperature.
For the preparation of (II), tert-butylamine (3.4 g, 46.8 mmol) was added to a solution of P(O)Cl3 (1.2 g, 7.8 mmol) in dry chloroform (30 ml) at 273 K. After stirring for 4 h, the solvent was evaporated [in vacuo? by heating?] and the product was washed with distilled water. Single crystals of (II) were obtained fortuitously from a reaction between (II), Zn(CH3COO)2.2H2O and piperazine in CH3OH under reflux, followed by slow evaporation of the filtered solution at room temperature.
For (I), all H atoms belonging to nondisordered groups were located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry, with C—H = 0.93–0.98 Å and N—H = 0.86–0.89 Å, and with Uiso(H) = 1.2–1.5Ueq(parent atom), after which the positions were refined with riding constraints. Geometric similarity restraints were used between the two different tert-butyl groups of each of the five disordered assemblies. Displacement similarity restraints were used for a number of the disordered groups in the tert-butyl assemblies. The occupancies of the disordered groups were initially refined, keeping the total occupancy fixed at 1 for each assembly, until the largest ratio of the final least-squares parameter shift to the final standard uncertainty was below 0.05. Then the occupancies were fixed, accelerating the final convergence. Despite the extensive modelling of the disorder in the tert-butyl assemblies, the final R residuals remain fairly large [R = 0.0961 for all reflections with I > -3σ(I) and R = 0.0609 for reflections with I > 2σ(I)]. This is most probably due to additional finer unresolved and unmodelled disorder, such as in the hitherto untreated tert-butyl assemblies, or splitting over more than two orientational sites for the five disordered tert-butyl assemblies.
For (II), all H atoms were discernible in difference Fourier maps and could be refined to reasonable geometries. In accord with common practice, H atoms attached to C atoms were kept in ideal positions during the refinement, with C—H = 0.96 Å. The methyl H atoms were allowed to rotate freely about the adjacent C—C bonds. The positions of the N-bound H atoms were restrained to 0.87 (2) Å. All H atoms were refined with Uiso(H) = 1.5Ueq(C) for the methyl groups or 1.2Ueq(N) for –NH– groups.
For both compounds, data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007). Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for (I); JANA2006 (Petříček et al., 2006) for (II). For both compounds, molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) and enCIFer (Allen et al., 2004) for (I); JANA2006 (Petříček et al., 2006) and enCIFer (Allen et al., 2004) for (II).
C10H26N3OP | F(000) = 1560.006 |
Mr = 235.31 | Dx = 1.064 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 11069 reflections |
a = 12.0615 (4) Å | θ = 1.5–29.1° |
b = 21.2567 (7) Å | µ = 0.17 mm−1 |
c = 17.1877 (6) Å | T = 150 K |
β = 90.529 (3)° | Rod, colourless |
V = 4406.5 (3) Å3 | 0.40 × 0.25 × 0.22 mm |
Z = 12 |
Agilent Gemini-S with Sapphire3 detector diffractometer | 17386 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 11821 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
Detector resolution: 16.0143 pixels mm-1 | θmax = 29.1°, θmin = 1.5° |
ω scans | h = −16→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −24→26 |
Tmin = 0.558, Tmax = 1.000 | l = −23→22 |
29385 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.061 | Method = Modified Sheldrick
w = 1/[σ2(F2) + ( 0.08P)2 + 1.62P], where P = (max(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.161 | (Δ/σ)max = 0.006 |
S = 0.92 | Δρmax = 0.53 e Å−3 |
17382 reflections | Δρmin = −0.57 e Å−3 |
947 parameters | Absolute structure: Flack (1983), with how many Friedel pairs? |
207 restraints | Absolute structure parameter: 0.00 (8) |
Primary atom site location: structure-invariant direct methods |
C10H26N3OP | V = 4406.5 (3) Å3 |
Mr = 235.31 | Z = 12 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.0615 (4) Å | µ = 0.17 mm−1 |
b = 21.2567 (7) Å | T = 150 K |
c = 17.1877 (6) Å | 0.40 × 0.25 × 0.22 mm |
β = 90.529 (3)° |
Agilent Gemini-S with Sapphire3 detector diffractometer | 17386 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 11821 reflections with I > 2σ(I) |
Tmin = 0.558, Tmax = 1.000 | Rint = 0.051 |
29385 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.161 | Δρmax = 0.53 e Å−3 |
S = 0.92 | Δρmin = −0.57 e Å−3 |
17382 reflections | Absolute structure: Flack (1983), with how many Friedel pairs? |
947 parameters | Absolute structure parameter: 0.00 (8) |
207 restraints |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat with a nominal stability of 0.1 K. Absorption correction: CrysAlis PRO (Agilent, 2010), multi-scan using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Refinement. Five tert-butyl groups were found to be disordered: the additional group was located by Fourier difference maps and matched with the preponderant groups using SAME restraint instructions. The relative site occupancies were refined and found to be in between 0.166 and 0.834. In the final refinement cycles the occupancies were fixed. Geometrical restraints were used to have similar geometries for the disordered tert-butyl groups. In total 207 restraints were used. Two reflections (1 - 1 0; 1 2 1) were omitted from the refinement, because some of the symmetry related equivalents were masked by the (asymmetric) Gemini beamstop. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.77812 (8) | 0.42010 (6) | 1.09815 (7) | 0.0360 | |
O2 | 0.6695 (2) | 0.44182 (15) | 1.06764 (17) | 0.0446 | |
N3 | 0.7716 (3) | 0.42415 (19) | 1.1936 (2) | 0.0486 | |
C4 | 0.6800 (4) | 0.4518 (3) | 1.2352 (3) | 0.0709 | |
H41 | 0.6685 | 0.4298 | 1.2832 | 0.1079* | |
H42 | 0.6968 | 0.4952 | 1.2466 | 0.1081* | |
H43 | 0.6144 | 0.4502 | 1.2030 | 0.1079* | |
C5 | 0.8696 (4) | 0.4146 (4) | 1.2419 (3) | 0.0868 | |
H51 | 0.8510 | 0.3916 | 1.2887 | 0.1273* | |
H52 | 0.8996 | 0.4547 | 1.2566 | 0.1270* | |
H53 | 0.9243 | 0.3915 | 1.2134 | 0.1269* | |
N6 | 0.8868 (3) | 0.45864 (15) | 1.0673 (2) | 0.0428 | |
H61 | 0.9335 | 0.4365 | 1.0417 | 0.0529* | |
C7 | 0.8936 (3) | 0.5275 (2) | 1.0539 (3) | 0.0513 | |
C8 | 1.0176 (4) | 0.5433 (2) | 1.0512 (3) | 0.0611 | |
H81 | 1.0514 | 0.5335 | 1.1006 | 0.0915* | |
H82 | 1.0522 | 0.5198 | 1.0107 | 0.0918* | |
H83 | 1.0267 | 0.5874 | 1.0402 | 0.0920* | |
C9 | 0.8411 (4) | 0.5628 (2) | 1.1211 (4) | 0.0810 | |
H91 | 0.8748 | 0.5497 | 1.1697 | 0.1249* | |
H92 | 0.8526 | 0.6071 | 1.1147 | 0.1249* | |
H93 | 0.7627 | 0.5546 | 1.1222 | 0.1249* | |
C10 | 0.8402 (5) | 0.5448 (3) | 0.9773 (4) | 0.0834 | |
H101 | 0.8491 | 0.5891 | 0.9674 | 0.1281* | |
H102 | 0.7622 | 0.5349 | 0.9785 | 0.1279* | |
H103 | 0.8749 | 0.5216 | 0.9360 | 0.1279* | |
N11 | 0.8172 (3) | 0.34884 (15) | 1.0769 (2) | 0.0495 | |
H111 | 0.8720 | 0.3462 | 1.0461 | 0.0606* | |
C12 | 0.7614 (3) | 0.28908 (13) | 1.0942 (2) | 0.0657 | |
C13 | 0.6698 (8) | 0.2954 (3) | 1.1508 (6) | 0.1180 | 0.4789 |
H131 | 0.6329 | 0.2555 | 1.1566 | 0.1749* | 0.4789 |
H132 | 0.6176 | 0.3263 | 1.1316 | 0.1749* | 0.4789 |
H133 | 0.7001 | 0.3088 | 1.2004 | 0.1751* | 0.4789 |
C14 | 0.7228 (9) | 0.2610 (4) | 1.0187 (5) | 0.1049 | 0.4789 |
H141 | 0.7705 | 0.2732 | 0.9771 | 0.1569* | 0.4789 |
H142 | 0.7227 | 0.2160 | 1.0228 | 0.1571* | 0.4789 |
H143 | 0.6488 | 0.2752 | 1.0071 | 0.1570* | 0.4789 |
C15 | 0.8523 (7) | 0.2461 (4) | 1.1331 (7) | 0.1212 | 0.4789 |
H151 | 0.8169 | 0.2026 | 1.1410 | 0.1659* | 0.4789 |
H152 | 0.9170 | 0.2440 | 1.0946 | 0.1659* | 0.4789 |
H153 | 0.8758 | 0.2665 | 1.1855 | 0.1661* | 0.4789 |
C413 | 0.6381 (6) | 0.2963 (3) | 1.1090 (5) | 0.0503 | 0.5211 |
C414 | 0.7837 (7) | 0.2449 (3) | 1.0300 (6) | 0.1185 | 0.5211 |
H4141 | 0.7624 | 0.2030 | 1.0471 | 0.1680* | 0.5211 |
H4142 | 0.8629 | 0.2457 | 1.0192 | 0.1680* | 0.5211 |
H4143 | 0.7410 | 0.2569 | 0.9837 | 0.1678* | 0.5211 |
C415 | 0.8162 (6) | 0.2645 (3) | 1.1727 (6) | 0.1092 | 0.5211 |
H4151 | 0.7862 | 0.2237 | 1.1862 | 0.1460* | 0.5211 |
H4152 | 0.8004 | 0.2941 | 1.2139 | 0.1458* | 0.5211 |
H4153 | 0.8961 | 0.2617 | 1.1659 | 0.1461* | 0.5211 |
H4131 | 0.6053 | 0.2561 | 1.1191 | 0.0829* | 0.5211 |
H4132 | 0.6261 | 0.3230 | 1.1529 | 0.0830* | 0.5211 |
H4133 | 0.6034 | 0.3147 | 1.0643 | 0.0828* | 0.5211 |
P16 | 0.85943 (9) | 0.64004 (6) | 0.59774 (7) | 0.0411 | |
O17 | 0.7457 (2) | 0.66017 (16) | 0.57819 (18) | 0.0511 | |
N18 | 0.8681 (3) | 0.6366 (2) | 0.6926 (2) | 0.0567 | |
C19 | 0.9725 (4) | 0.6211 (3) | 0.7318 (3) | 0.0749 | |
H191 | 0.9577 | 0.6037 | 0.7825 | 0.1101* | |
H192 | 1.0174 | 0.6584 | 0.7370 | 0.1102* | |
H193 | 1.0112 | 0.5911 | 0.7010 | 0.1102* | |
C20 | 0.7787 (5) | 0.6468 (4) | 0.7459 (3) | 0.1017 | |
H201 | 0.8071 | 0.6552 | 0.7976 | 0.1480* | |
H202 | 0.7344 | 0.6817 | 0.7292 | 0.1481* | |
H203 | 0.7335 | 0.6097 | 0.7466 | 0.1481* | |
N21 | 0.9617 (3) | 0.68386 (16) | 0.5663 (2) | 0.0411 | |
H211 | 1.0030 | 0.6667 | 0.5324 | 0.0517* | |
C22 | 0.9685 (4) | 0.7535 (2) | 0.5714 (3) | 0.0468 | |
C23 | 1.0916 (4) | 0.7702 (2) | 0.5640 (3) | 0.0639 | |
H231 | 1.1005 | 0.8152 | 0.5661 | 0.0949* | |
H232 | 1.1187 | 0.7544 | 0.5150 | 0.0949* | |
H233 | 1.1321 | 0.7513 | 0.6066 | 0.0946* | |
C24 | 0.9015 (4) | 0.7833 (2) | 0.5058 (3) | 0.0616 | |
H241 | 0.9302 | 0.7700 | 0.4561 | 0.0920* | |
H242 | 0.9069 | 0.8285 | 0.5097 | 0.0922* | |
H243 | 0.8250 | 0.7709 | 0.5103 | 0.0919* | |
C25 | 0.9255 (5) | 0.7772 (3) | 0.6488 (3) | 0.0704 | |
H251 | 0.9666 | 0.7574 | 0.6910 | 0.1019* | |
H252 | 0.8476 | 0.7675 | 0.6534 | 0.1018* | |
H253 | 0.9361 | 0.8221 | 0.6514 | 0.1021* | |
N26 | 0.8986 (3) | 0.57148 (15) | 0.5632 (2) | 0.0506 | |
H261 | 0.9530 | 0.5725 | 0.5309 | 0.0628* | |
C27 | 0.8327 (2) | 0.51286 (13) | 0.56396 (17) | 0.0518 | |
C28 | 0.7694 (5) | 0.5055 (2) | 0.6416 (3) | 0.0775 | 0.8337 |
H281 | 0.8201 | 0.5082 | 0.6850 | 0.1148* | 0.8337 |
H282 | 0.7154 | 0.5382 | 0.6457 | 0.1149* | 0.8337 |
H283 | 0.7326 | 0.4654 | 0.6431 | 0.1150* | 0.8337 |
C29 | 0.7537 (4) | 0.5135 (2) | 0.4966 (3) | 0.0753 | 0.8337 |
H291 | 0.7039 | 0.5485 | 0.5010 | 0.1099* | 0.8337 |
H292 | 0.7948 | 0.5169 | 0.4491 | 0.1098* | 0.8337 |
H293 | 0.7121 | 0.4748 | 0.4955 | 0.1101* | 0.8337 |
C30 | 0.9138 (4) | 0.4576 (2) | 0.5597 (3) | 0.0656 | 0.8337 |
H301 | 0.8735 | 0.4186 | 0.5618 | 0.0970* | 0.8337 |
H302 | 0.9537 | 0.4599 | 0.5118 | 0.0969* | 0.8337 |
H303 | 0.9654 | 0.4605 | 0.6026 | 0.0970* | 0.8337 |
C428 | 0.7099 (9) | 0.5260 (3) | 0.5855 (15) | 0.0697 | 0.1663 |
H4281 | 0.6682 | 0.4879 | 0.5797 | 0.0900* | 0.1663 |
H4282 | 0.7046 | 0.5407 | 0.6382 | 0.0900* | 0.1663 |
H4283 | 0.6802 | 0.5574 | 0.5508 | 0.0900* | 0.1663 |
C429 | 0.8395 (17) | 0.4820 (7) | 0.4850 (7) | 0.0854 | 0.1663 |
H4291 | 0.8252 | 0.4370 | 0.4904 | 0.1340* | 0.1663 |
H4292 | 0.9134 | 0.4886 | 0.4638 | 0.1340* | 0.1663 |
H4293 | 0.7841 | 0.5007 | 0.4503 | 0.1340* | 0.1663 |
C430 | 0.8800 (14) | 0.4710 (6) | 0.6281 (11) | 0.0837 | 0.1663 |
H4301 | 0.8537 | 0.4288 | 0.6209 | 0.1120* | 0.1663 |
H4302 | 0.8556 | 0.4867 | 0.6775 | 0.1120* | 0.1663 |
H4303 | 0.9595 | 0.4716 | 0.6267 | 0.1120* | 0.1663 |
P31 | 0.51417 (8) | 0.73870 (6) | 0.46963 (6) | 0.0348 | |
O32 | 0.4065 (2) | 0.70654 (13) | 0.45762 (16) | 0.0392 | |
N33 | 0.5575 (3) | 0.74708 (17) | 0.55954 (19) | 0.0462 | |
H331 | 0.6135 | 0.7246 | 0.5719 | 0.0558* | |
C34 | 0.4987 (2) | 0.77756 (15) | 0.62334 (18) | 0.0526 | |
C35 | 0.3967 (5) | 0.8129 (4) | 0.6001 (3) | 0.0887 | 0.7278 |
H351 | 0.3570 | 0.8258 | 0.6453 | 0.1378* | 0.7278 |
H352 | 0.3494 | 0.7870 | 0.5686 | 0.1378* | 0.7278 |
H353 | 0.4181 | 0.8495 | 0.5708 | 0.1382* | 0.7278 |
C36 | 0.5788 (5) | 0.8163 (4) | 0.6693 (5) | 0.1538 | 0.7278 |
H362 | 0.5427 | 0.8301 | 0.7159 | 0.2309* | 0.7278 |
H361 | 0.6026 | 0.8522 | 0.6398 | 0.2309* | 0.7278 |
H363 | 0.6416 | 0.7907 | 0.6826 | 0.2311* | 0.7278 |
C37 | 0.4595 (8) | 0.7231 (4) | 0.6768 (5) | 0.1724 | 0.7278 |
H371 | 0.4340 | 0.7406 | 0.7255 | 0.2560* | 0.7278 |
H372 | 0.3991 | 0.7018 | 0.6514 | 0.2559* | 0.7278 |
H373 | 0.5192 | 0.6940 | 0.6866 | 0.2561* | 0.7278 |
C435 | 0.3768 (7) | 0.7771 (5) | 0.6166 (4) | 0.0451 | 0.2722 |
H4351 | 0.3370 | 0.7780 | 0.6652 | 0.0780* | 0.2722 |
H4352 | 0.4231 | 0.8157 | 0.6051 | 0.0800* | 0.2722 |
H4353 | 0.3460 | 0.7555 | 0.5718 | 0.0780* | 0.2722 |
C436 | 0.5464 (8) | 0.8433 (5) | 0.6353 (6) | 0.0596 | 0.2722 |
H4361 | 0.5150 | 0.8617 | 0.6811 | 0.0909* | 0.2722 |
H4362 | 0.6253 | 0.8403 | 0.6416 | 0.0910* | 0.2722 |
H4363 | 0.5302 | 0.8695 | 0.5911 | 0.0909* | 0.2722 |
C437 | 0.5284 (9) | 0.7383 (5) | 0.6978 (5) | 0.0568 | 0.2722 |
H4371 | 0.4980 | 0.7592 | 0.7429 | 0.0809* | 0.2722 |
H4372 | 0.6080 | 0.7357 | 0.7031 | 0.0809* | 0.2722 |
H4373 | 0.4976 | 0.6964 | 0.6934 | 0.0810* | 0.2722 |
N38 | 0.6242 (3) | 0.70515 (16) | 0.43239 (19) | 0.0388 | |
H381 | 0.6741 | 0.6942 | 0.4663 | 0.0467* | |
C39 | 0.6310 (3) | 0.6736 (2) | 0.3564 (2) | 0.0451 | |
C40 | 0.5694 (4) | 0.6107 (2) | 0.3576 (3) | 0.0537 | |
H401 | 0.5986 | 0.5858 | 0.3993 | 0.0830* | |
H402 | 0.4919 | 0.6180 | 0.3654 | 0.0828* | |
H403 | 0.5803 | 0.5889 | 0.3091 | 0.0828* | |
C41 | 0.5804 (4) | 0.7155 (3) | 0.2938 (3) | 0.0607 | |
H411 | 0.6164 | 0.7556 | 0.2940 | 0.0908* | |
H412 | 0.5020 | 0.7211 | 0.3034 | 0.0907* | |
H413 | 0.5892 | 0.6962 | 0.2435 | 0.0906* | |
C42 | 0.7541 (4) | 0.6643 (3) | 0.3405 (3) | 0.0622 | |
H421 | 0.7634 | 0.6426 | 0.2918 | 0.0959* | |
H422 | 0.7870 | 0.6398 | 0.3823 | 0.0957* | |
H423 | 0.7908 | 0.7045 | 0.3381 | 0.0958* | |
N43 | 0.5001 (3) | 0.80862 (17) | 0.4305 (2) | 0.0509 | |
C44 | 0.3972 (4) | 0.8321 (2) | 0.3984 (4) | 0.0719 | |
H441 | 0.3874 | 0.8748 | 0.4158 | 0.1061* | |
H442 | 0.3352 | 0.8065 | 0.4159 | 0.1060* | |
H443 | 0.3994 | 0.8313 | 0.3420 | 0.1062* | |
C45 | 0.5940 (5) | 0.8523 (2) | 0.4265 (4) | 0.0780 | |
H451 | 0.5696 | 0.8935 | 0.4463 | 0.1141* | |
H452 | 0.6556 | 0.8354 | 0.4588 | 0.1140* | |
H453 | 0.6177 | 0.8562 | 0.3721 | 0.1140* | |
P46 | 0.45278 (8) | 0.50924 (6) | 0.93811 (6) | 0.0351 | |
O47 | 0.3430 (2) | 0.47949 (13) | 0.92945 (16) | 0.0398 | |
N48 | 0.4900 (3) | 0.53223 (17) | 1.0250 (2) | 0.0410 | |
H481 | 0.5415 | 0.5110 | 1.0473 | 0.0504* | |
C49 | 0.4375 (3) | 0.5816 (2) | 1.0738 (3) | 0.0454 | |
C50 | 0.3141 (3) | 0.5847 (2) | 1.0582 (3) | 0.0494 | |
H501 | 0.2819 | 0.6158 | 1.0915 | 0.0750* | |
H502 | 0.2999 | 0.5956 | 1.0045 | 0.0748* | |
H503 | 0.2808 | 0.5446 | 1.0684 | 0.0746* | |
C51 | 0.4890 (4) | 0.6463 (3) | 1.0556 (4) | 0.0799 | |
H511 | 0.5678 | 0.6440 | 1.0641 | 0.1180* | |
H512 | 0.4573 | 0.6775 | 1.0895 | 0.1178* | |
H513 | 0.4743 | 0.6576 | 1.0021 | 0.1177* | |
C52 | 0.4600 (5) | 0.5644 (3) | 1.1568 (3) | 0.0797 | |
H521 | 0.4272 | 0.5245 | 1.1680 | 0.1188* | |
H522 | 0.4277 | 0.5957 | 1.1900 | 0.1189* | |
H523 | 0.5386 | 0.5630 | 1.1655 | 0.1189* | |
N53 | 0.4512 (3) | 0.57281 (18) | 0.8829 (2) | 0.0471 | |
C54 | 0.3617 (4) | 0.5867 (2) | 0.8277 (3) | 0.0592 | |
H541 | 0.3471 | 0.6312 | 0.8275 | 0.0861* | |
H542 | 0.2950 | 0.5650 | 0.8429 | 0.0860* | |
H543 | 0.3821 | 0.5739 | 0.7762 | 0.0858* | |
C55 | 0.5533 (4) | 0.6069 (3) | 0.8660 (3) | 0.0721 | |
H551 | 0.5394 | 0.6515 | 0.8660 | 0.1070* | |
H552 | 0.6090 | 0.5968 | 0.9047 | 0.1070* | |
H553 | 0.5793 | 0.5943 | 0.8156 | 0.1070* | |
N56 | 0.5611 (3) | 0.46559 (17) | 0.9172 (2) | 0.0420 | |
H561 | 0.6096 | 0.4605 | 0.9546 | 0.0512* | |
C57 | 0.5661 (4) | 0.4198 (2) | 0.8519 (3) | 0.0506 | |
C58 | 0.6904 (4) | 0.4067 (3) | 0.8387 (3) | 0.0632 | |
H581 | 0.6992 | 0.3752 | 0.7996 | 0.0979* | |
H582 | 0.7278 | 0.4444 | 0.8225 | 0.0979* | |
H583 | 0.7236 | 0.3919 | 0.8867 | 0.0977* | |
C59 | 0.5082 (4) | 0.3599 (3) | 0.8731 (4) | 0.0793 | |
H591 | 0.5429 | 0.3420 | 0.9188 | 0.1176* | |
H592 | 0.5143 | 0.3312 | 0.8298 | 0.1180* | |
H593 | 0.4308 | 0.3684 | 0.8830 | 0.1180* | |
C60 | 0.5157 (5) | 0.4487 (3) | 0.7787 (3) | 0.0794 | |
H601 | 0.5207 | 0.4195 | 0.7361 | 0.1219* | |
H602 | 0.4387 | 0.4587 | 0.7878 | 0.1219* | |
H603 | 0.5556 | 0.4867 | 0.7656 | 0.1222* | |
P61 | 1.18574 (9) | 0.59160 (6) | 0.41617 (7) | 0.0398 | |
O62 | 1.0727 (2) | 0.59868 (15) | 0.44844 (17) | 0.0475 | |
N63 | 1.2299 (3) | 0.64756 (17) | 0.35813 (19) | 0.0406 | |
H631 | 1.2843 | 0.6697 | 0.3760 | 0.0522* | |
C64 | 1.1625 (4) | 0.6776 (3) | 0.2964 (3) | 0.0526 | |
C65 | 1.2416 (4) | 0.7134 (3) | 0.2434 (3) | 0.0594 | |
H651 | 1.2790 | 0.7454 | 0.2736 | 0.0879* | |
H652 | 1.2957 | 0.6851 | 0.2226 | 0.0879* | |
H653 | 1.2003 | 0.7329 | 0.2010 | 0.0878* | |
C66 | 1.0798 (4) | 0.7241 (3) | 0.3318 (3) | 0.0844 | |
H661 | 1.1188 | 0.7580 | 0.3574 | 0.1269* | |
H662 | 1.0322 | 0.7411 | 0.2916 | 0.1268* | |
H663 | 1.0352 | 0.7021 | 0.3699 | 0.1268* | |
C67 | 1.1007 (5) | 0.6277 (3) | 0.2494 (3) | 0.0949 | |
H671 | 1.0580 | 0.6482 | 0.2093 | 0.1387* | |
H672 | 1.0525 | 0.6048 | 0.2836 | 0.1390* | |
H673 | 1.1536 | 0.5992 | 0.2261 | 0.1389* | |
N68 | 1.2898 (3) | 0.58920 (17) | 0.4767 (2) | 0.0412 | |
H681 | 1.3321 | 0.6215 | 0.4750 | 0.0510* | |
C69 | 1.2953 (4) | 0.5548 (2) | 0.5514 (3) | 0.0525 | |
C70 | 1.4177 (4) | 0.5458 (2) | 0.5721 (3) | 0.0581 | |
H701 | 1.4259 | 0.5246 | 0.6210 | 0.0899* | |
H702 | 1.4538 | 0.5211 | 0.5325 | 0.0899* | |
H703 | 1.4549 | 0.5860 | 0.5768 | 0.0896* | |
C71 | 1.2344 (4) | 0.5905 (3) | 0.6147 (3) | 0.0754 | |
H711 | 1.2680 | 0.6316 | 0.6207 | 0.1148* | |
H712 | 1.2387 | 0.5679 | 0.6635 | 0.1149* | |
H713 | 1.1577 | 0.5957 | 0.5991 | 0.1150* | |
C72 | 1.2412 (4) | 0.4891 (2) | 0.5422 (4) | 0.0812 | |
H721 | 1.2475 | 0.4666 | 0.5904 | 0.1180* | |
H722 | 1.1639 | 0.4940 | 0.5282 | 0.1179* | |
H723 | 1.2780 | 0.4663 | 0.5014 | 0.1179* | |
N73 | 1.1872 (3) | 0.52511 (19) | 0.3667 (2) | 0.0584 | |
C74 | 1.2886 (5) | 0.5036 (3) | 0.3301 (4) | 0.0826 | |
H741 | 1.2744 | 0.4680 | 0.2980 | 0.1263* | |
H742 | 1.3429 | 0.4931 | 0.3691 | 0.1263* | |
H743 | 1.3176 | 0.5368 | 0.2985 | 0.1260* | |
C75 | 1.0927 (5) | 0.4841 (3) | 0.3534 (4) | 0.1063 | |
H751 | 1.1016 | 0.4615 | 0.3049 | 0.1560* | |
H752 | 1.0861 | 0.4543 | 0.3958 | 0.1561* | |
H753 | 1.0260 | 0.5096 | 0.3500 | 0.1561* | |
P76 | 1.13177 (9) | 0.35437 (6) | 0.95440 (7) | 0.0401 | |
O77 | 1.0194 (2) | 0.36291 (13) | 0.98729 (18) | 0.0492 | |
N78 | 1.1415 (3) | 0.27985 (18) | 0.9281 (3) | 0.0616 | |
C79 | 1.0536 (5) | 0.2352 (2) | 0.9373 (4) | 0.0914 | |
H791 | 1.0517 | 0.2077 | 0.8933 | 0.1381* | |
H792 | 1.0658 | 0.2117 | 0.9841 | 0.1380* | |
H793 | 0.9844 | 0.2573 | 0.9408 | 0.1381* | |
C80 | 1.2414 (4) | 0.2535 (2) | 0.8973 (4) | 0.0667 | |
H801 | 1.2228 | 0.2266 | 0.8541 | 0.0981* | |
H802 | 1.2783 | 0.2301 | 0.9385 | 0.0982* | |
H803 | 1.2879 | 0.2873 | 0.8795 | 0.0981* | |
N81 | 1.1620 (3) | 0.39666 (16) | 0.87966 (19) | 0.0426 | |
H811 | 1.2179 | 0.4210 | 0.8859 | 0.0523* | |
C82 | 1.1032 (3) | 0.40565 (16) | 0.80476 (19) | 0.0550 | |
C83 | 1.1545 (5) | 0.3554 (4) | 0.7460 (4) | 0.0803 | 0.6635 |
H831 | 1.1220 | 0.3607 | 0.6949 | 0.1190* | 0.6635 |
H832 | 1.1410 | 0.3133 | 0.7648 | 0.1190* | 0.6635 |
H833 | 1.2337 | 0.3627 | 0.7434 | 0.1190* | 0.6635 |
C84 | 0.9830 (5) | 0.3867 (4) | 0.8103 (3) | 0.0784 | 0.6635 |
H841 | 0.9460 | 0.4148 | 0.8457 | 0.1219* | 0.6635 |
H842 | 0.9484 | 0.3892 | 0.7597 | 0.1218* | 0.6635 |
H843 | 0.9773 | 0.3442 | 0.8296 | 0.1219* | 0.6635 |
C85 | 1.1271 (7) | 0.4684 (3) | 0.7708 (4) | 0.1092 | 0.6635 |
H851 | 1.1982 | 0.4850 | 0.7715 | 0.1299* | 0.6635 |
H852 | 1.0764 | 0.4861 | 0.7364 | 0.1300* | 0.6635 |
H853 | 1.0769 | 0.4989 | 0.8335 | 0.1720* | 0.6665 |
C483 | 1.0316 (12) | 0.3439 (5) | 0.7909 (6) | 0.0942 | 0.3365 |
H4831 | 0.9696 | 0.3524 | 0.7562 | 0.1600* | 0.3365 |
H4832 | 1.0807 | 0.3133 | 0.7676 | 0.1600* | 0.3365 |
H4833 | 1.0042 | 0.3282 | 0.8400 | 0.1600* | 0.3365 |
C484 | 1.0175 (12) | 0.4574 (6) | 0.8105 (5) | 0.1297 | 0.3365 |
H4841 | 0.9597 | 0.4489 | 0.7720 | 0.2071* | 0.3365 |
H4842 | 1.0487 | 0.4989 | 0.8016 | 0.2070* | 0.3365 |
H4843 | 0.9862 | 0.4561 | 0.8622 | 0.2069* | 0.3365 |
C485 | 1.1806 (6) | 0.4090 (8) | 0.7398 (5) | 0.1439 | 0.3365 |
H4851 | 1.1332 | 0.4130 | 0.6904 | 0.1759* | 0.3365 |
H4852 | 1.2252 | 0.4492 | 0.7499 | 0.1760* | 0.3365 |
H4853 | 1.2304 | 0.3705 | 0.7384 | 0.1760* | 0.3365 |
N86 | 1.2366 (3) | 0.37155 (16) | 1.01107 (19) | 0.0457 | |
H861 | 1.2779 | 0.4013 | 0.9952 | 0.0549* | |
C87 | 1.2566 (3) | 0.35460 (16) | 1.09292 (18) | 0.0568 | |
C88 | 1.1826 (7) | 0.3949 (4) | 1.1459 (3) | 0.0992 | 0.6788 |
H881 | 1.2060 | 0.4380 | 1.1444 | 0.1530* | 0.6788 |
H882 | 1.1068 | 0.3923 | 1.1284 | 0.1529* | 0.6788 |
H883 | 1.1875 | 0.3797 | 1.1988 | 0.1530* | 0.6788 |
C89 | 1.3718 (6) | 0.3580 (4) | 1.1105 (3) | 0.1348 | 0.6788 |
H891 | 1.3813 | 0.3525 | 1.1659 | 0.2069* | 0.6788 |
H892 | 1.4143 | 0.3271 | 1.0827 | 0.2070* | 0.6788 |
H893 | 1.3970 | 0.3995 | 1.0962 | 0.2068* | 0.6788 |
C90 | 1.2100 (8) | 0.2846 (4) | 1.1049 (4) | 0.1235 | 0.6788 |
H901 | 1.2557 | 0.2550 | 1.0774 | 0.1741* | 0.6788 |
H902 | 1.2117 | 0.2753 | 1.1598 | 0.1740* | 0.6788 |
H903 | 1.1350 | 0.2819 | 1.0857 | 0.1740* | 0.6788 |
C488 | 1.1450 (8) | 0.3445 (6) | 1.1345 (4) | 0.1008 | 0.3212 |
H4881 | 1.1537 | 0.3117 | 1.1725 | 0.1780* | 0.3212 |
H4882 | 1.1911 | 0.3848 | 1.1399 | 0.1310* | 0.3212 |
H4883 | 1.0866 | 0.3422 | 1.0960 | 0.1781* | 0.3212 |
C489 | 1.3289 (10) | 0.4004 (4) | 1.1293 (4) | 0.0947 | 0.3212 |
H4891 | 1.3375 | 0.3886 | 1.1843 | 0.2100* | 0.3212 |
H4892 | 1.4024 | 0.4039 | 1.1056 | 0.2099* | 0.3212 |
H4893 | 1.2896 | 0.4408 | 1.1250 | 0.2101* | 0.3212 |
C490 | 1.3122 (10) | 0.2856 (4) | 1.0935 (4) | 0.0458 | 0.3212 |
H4901 | 1.3294 | 0.2740 | 1.1463 | 0.0740* | 0.3212 |
H4902 | 1.3794 | 0.2877 | 1.0642 | 0.0740* | 0.3212 |
H4903 | 1.2642 | 0.2547 | 1.0705 | 0.0740* | 0.3212 |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0331 (5) | 0.0333 (6) | 0.0416 (6) | −0.0022 (4) | 0.0001 (5) | −0.0010 (5) |
O2 | 0.0312 (14) | 0.0569 (19) | 0.0455 (17) | −0.0021 (12) | −0.0057 (13) | 0.0061 (15) |
N3 | 0.042 (2) | 0.059 (2) | 0.045 (2) | 0.0076 (18) | −0.0048 (17) | −0.003 (2) |
C4 | 0.081 (4) | 0.077 (4) | 0.056 (3) | 0.017 (3) | 0.019 (3) | −0.003 (3) |
C5 | 0.061 (4) | 0.136 (6) | 0.063 (4) | 0.012 (4) | −0.021 (3) | −0.005 (4) |
N6 | 0.0366 (18) | 0.0280 (19) | 0.064 (2) | −0.0009 (14) | 0.0056 (17) | −0.0030 (18) |
C7 | 0.038 (2) | 0.027 (2) | 0.089 (4) | −0.0056 (17) | 0.005 (2) | 0.002 (2) |
C8 | 0.046 (3) | 0.037 (3) | 0.100 (4) | −0.006 (2) | 0.003 (3) | 0.000 (3) |
C9 | 0.068 (3) | 0.032 (3) | 0.144 (6) | −0.007 (2) | 0.035 (4) | −0.019 (3) |
C10 | 0.067 (4) | 0.054 (3) | 0.129 (6) | −0.012 (3) | −0.018 (4) | 0.038 (4) |
N11 | 0.049 (2) | 0.0306 (19) | 0.069 (3) | −0.0070 (16) | 0.0208 (19) | −0.0044 (18) |
C12 | 0.048 (3) | 0.031 (3) | 0.118 (5) | −0.0089 (19) | 0.018 (3) | 0.004 (3) |
C13 | 0.136 (12) | 0.066 (10) | 0.153 (18) | −0.039 (8) | 0.107 (13) | −0.018 (9) |
C14 | 0.079 (9) | 0.111 (13) | 0.125 (11) | −0.072 (8) | 0.002 (7) | −0.031 (9) |
C15 | 0.096 (8) | 0.076 (8) | 0.191 (11) | −0.018 (6) | −0.021 (7) | 0.073 (8) |
C413 | 0.043 (4) | 0.044 (6) | 0.064 (7) | −0.013 (4) | 0.005 (4) | 0.009 (5) |
C414 | 0.084 (8) | 0.047 (6) | 0.225 (10) | −0.032 (5) | 0.071 (7) | −0.056 (6) |
C415 | 0.044 (5) | 0.074 (9) | 0.209 (9) | −0.010 (6) | −0.018 (7) | 0.084 (7) |
P16 | 0.0347 (5) | 0.0439 (7) | 0.0448 (7) | 0.0006 (5) | 0.0024 (5) | 0.0016 (6) |
O17 | 0.0316 (15) | 0.067 (2) | 0.054 (2) | 0.0025 (14) | −0.0013 (14) | 0.0043 (17) |
N18 | 0.042 (2) | 0.078 (3) | 0.050 (2) | 0.002 (2) | 0.0073 (18) | 0.009 (2) |
C19 | 0.068 (4) | 0.093 (5) | 0.064 (4) | 0.007 (3) | −0.017 (3) | 0.012 (3) |
C20 | 0.075 (4) | 0.171 (8) | 0.060 (4) | 0.024 (4) | 0.020 (3) | 0.007 (4) |
N21 | 0.0394 (19) | 0.036 (2) | 0.048 (2) | 0.0003 (15) | 0.0060 (16) | 0.0000 (17) |
C22 | 0.046 (2) | 0.038 (3) | 0.056 (3) | −0.0015 (19) | −0.004 (2) | −0.003 (2) |
C23 | 0.055 (3) | 0.049 (3) | 0.087 (4) | −0.014 (2) | −0.006 (3) | −0.001 (3) |
C24 | 0.061 (3) | 0.043 (3) | 0.082 (4) | 0.002 (2) | −0.008 (3) | −0.005 (3) |
C25 | 0.085 (4) | 0.050 (3) | 0.076 (4) | 0.007 (3) | 0.003 (3) | −0.025 (3) |
N26 | 0.045 (2) | 0.037 (2) | 0.071 (3) | −0.0067 (16) | 0.0163 (19) | −0.0029 (19) |
C27 | 0.048 (3) | 0.040 (3) | 0.067 (3) | −0.011 (2) | −0.005 (2) | 0.008 (3) |
C28 | 0.081 (5) | 0.062 (4) | 0.090 (5) | −0.024 (4) | 0.019 (4) | 0.016 (4) |
C29 | 0.068 (4) | 0.066 (5) | 0.091 (5) | −0.026 (4) | −0.035 (4) | 0.018 (4) |
C30 | 0.065 (4) | 0.036 (3) | 0.096 (5) | −0.007 (3) | −0.012 (4) | 0.013 (4) |
C428 | 0.065 (16) | 0.035 (15) | 0.11 (2) | −0.021 (12) | 0.008 (17) | 0.020 (16) |
C429 | 0.12 (3) | 0.017 (14) | 0.12 (2) | −0.022 (16) | 0.04 (2) | 0.007 (17) |
C430 | 0.08 (2) | 0.030 (14) | 0.14 (2) | −0.003 (14) | 0.00 (2) | 0.011 (14) |
P31 | 0.0363 (5) | 0.0311 (5) | 0.0371 (6) | −0.0032 (4) | −0.0021 (5) | −0.0007 (5) |
O32 | 0.0374 (15) | 0.0349 (16) | 0.0453 (17) | −0.0078 (12) | −0.0043 (13) | −0.0016 (13) |
N33 | 0.0404 (19) | 0.054 (2) | 0.044 (2) | 0.0065 (17) | −0.0012 (16) | −0.0094 (19) |
C34 | 0.053 (3) | 0.052 (3) | 0.053 (3) | 0.007 (2) | 0.003 (2) | −0.022 (2) |
C35 | 0.058 (5) | 0.116 (8) | 0.092 (7) | 0.040 (5) | −0.014 (4) | −0.052 (5) |
C36 | 0.066 (6) | 0.200 (11) | 0.194 (12) | 0.038 (6) | −0.045 (6) | −0.168 (11) |
C37 | 0.248 (14) | 0.123 (8) | 0.149 (11) | 0.060 (7) | 0.152 (10) | 0.044 (6) |
C435 | 0.038 (8) | 0.048 (11) | 0.050 (11) | −0.004 (6) | −0.001 (6) | −0.026 (8) |
C436 | 0.021 (6) | 0.063 (6) | 0.094 (12) | 0.005 (6) | −0.008 (8) | −0.033 (6) |
C437 | 0.047 (9) | 0.084 (10) | 0.039 (5) | 0.004 (9) | −0.006 (7) | −0.026 (6) |
N38 | 0.0395 (18) | 0.044 (2) | 0.0326 (19) | 0.0010 (15) | −0.0046 (15) | −0.0044 (17) |
C39 | 0.044 (2) | 0.058 (3) | 0.033 (2) | 0.004 (2) | 0.0003 (19) | −0.001 (2) |
C40 | 0.060 (3) | 0.056 (3) | 0.045 (3) | 0.000 (2) | 0.000 (2) | −0.017 (2) |
C41 | 0.066 (3) | 0.080 (4) | 0.036 (3) | 0.002 (3) | −0.001 (2) | 0.005 (3) |
C42 | 0.046 (3) | 0.091 (4) | 0.050 (3) | 0.008 (3) | 0.006 (2) | −0.016 (3) |
N43 | 0.049 (2) | 0.033 (2) | 0.071 (3) | −0.0057 (17) | 0.001 (2) | 0.008 (2) |
C44 | 0.073 (4) | 0.045 (3) | 0.098 (5) | 0.009 (3) | −0.012 (3) | 0.023 (3) |
C45 | 0.086 (4) | 0.041 (3) | 0.107 (5) | −0.028 (3) | −0.001 (3) | 0.019 (3) |
P46 | 0.0355 (5) | 0.0371 (6) | 0.0327 (6) | −0.0029 (4) | −0.0009 (4) | −0.0013 (5) |
O47 | 0.0376 (15) | 0.0433 (17) | 0.0385 (16) | −0.0054 (12) | −0.0038 (13) | 0.0026 (14) |
N48 | 0.0412 (19) | 0.043 (2) | 0.039 (2) | 0.0065 (15) | 0.0005 (16) | −0.0049 (17) |
C49 | 0.039 (2) | 0.051 (3) | 0.047 (3) | 0.0034 (19) | −0.007 (2) | −0.017 (2) |
C50 | 0.044 (2) | 0.050 (3) | 0.054 (3) | 0.009 (2) | 0.003 (2) | −0.013 (2) |
C51 | 0.058 (3) | 0.058 (4) | 0.124 (5) | −0.011 (3) | 0.004 (3) | −0.043 (4) |
C52 | 0.081 (4) | 0.112 (5) | 0.046 (3) | 0.050 (4) | −0.011 (3) | −0.034 (3) |
N53 | 0.041 (2) | 0.053 (2) | 0.048 (2) | −0.0031 (16) | −0.0018 (17) | 0.0132 (19) |
C54 | 0.062 (3) | 0.059 (3) | 0.057 (3) | 0.008 (3) | −0.005 (3) | 0.005 (3) |
C55 | 0.062 (3) | 0.066 (4) | 0.089 (4) | −0.012 (3) | 0.015 (3) | 0.028 (3) |
N56 | 0.0404 (19) | 0.050 (2) | 0.0351 (19) | 0.0002 (16) | −0.0051 (16) | −0.0079 (18) |
C57 | 0.050 (3) | 0.060 (3) | 0.042 (3) | 0.007 (2) | 0.002 (2) | −0.017 (2) |
C58 | 0.052 (3) | 0.083 (4) | 0.055 (3) | 0.010 (3) | 0.006 (2) | −0.020 (3) |
C59 | 0.065 (3) | 0.068 (4) | 0.104 (5) | −0.002 (3) | 0.011 (3) | −0.040 (4) |
C60 | 0.081 (4) | 0.109 (5) | 0.048 (3) | 0.035 (4) | −0.011 (3) | −0.031 (3) |
P61 | 0.0364 (6) | 0.0392 (6) | 0.0438 (7) | −0.0027 (5) | −0.0005 (5) | −0.0062 (5) |
O62 | 0.0362 (15) | 0.0534 (19) | 0.0530 (19) | −0.0028 (13) | 0.0023 (14) | −0.0024 (16) |
N63 | 0.0357 (18) | 0.049 (2) | 0.037 (2) | 0.0009 (15) | −0.0093 (15) | −0.0026 (17) |
C64 | 0.049 (3) | 0.077 (4) | 0.032 (2) | 0.006 (2) | −0.008 (2) | 0.005 (2) |
C65 | 0.066 (3) | 0.070 (3) | 0.042 (3) | 0.002 (3) | −0.005 (2) | 0.015 (3) |
C66 | 0.060 (3) | 0.125 (6) | 0.068 (4) | 0.046 (3) | 0.008 (3) | 0.023 (4) |
C67 | 0.091 (4) | 0.138 (6) | 0.055 (4) | −0.041 (4) | −0.038 (3) | 0.018 (4) |
N68 | 0.0345 (17) | 0.0386 (19) | 0.050 (2) | −0.0055 (15) | −0.0026 (16) | 0.0093 (18) |
C69 | 0.043 (2) | 0.051 (3) | 0.063 (3) | 0.004 (2) | −0.002 (2) | 0.026 (3) |
C70 | 0.047 (3) | 0.065 (3) | 0.062 (3) | 0.008 (2) | −0.007 (2) | 0.023 (3) |
C71 | 0.063 (3) | 0.104 (5) | 0.059 (3) | 0.028 (3) | 0.008 (3) | 0.030 (3) |
C72 | 0.058 (3) | 0.055 (3) | 0.130 (5) | −0.011 (2) | −0.005 (3) | 0.052 (4) |
N73 | 0.052 (2) | 0.055 (3) | 0.068 (3) | −0.0129 (19) | 0.004 (2) | −0.032 (2) |
C74 | 0.079 (4) | 0.065 (4) | 0.104 (5) | −0.008 (3) | 0.024 (3) | −0.040 (4) |
C75 | 0.083 (4) | 0.095 (5) | 0.141 (6) | −0.046 (4) | 0.033 (4) | −0.058 (5) |
P76 | 0.0410 (6) | 0.0255 (5) | 0.0539 (7) | 0.0003 (4) | 0.0110 (5) | −0.0012 (5) |
O77 | 0.0471 (17) | 0.0312 (16) | 0.070 (2) | −0.0015 (12) | 0.0217 (15) | −0.0049 (15) |
N78 | 0.052 (2) | 0.028 (2) | 0.105 (4) | 0.0002 (17) | 0.028 (2) | −0.012 (2) |
C79 | 0.079 (4) | 0.035 (3) | 0.161 (7) | −0.015 (3) | 0.046 (4) | −0.018 (4) |
C80 | 0.059 (3) | 0.044 (3) | 0.097 (4) | 0.010 (2) | 0.026 (3) | −0.010 (3) |
N81 | 0.0399 (19) | 0.042 (2) | 0.045 (2) | −0.0091 (15) | −0.0060 (17) | 0.0024 (17) |
C82 | 0.052 (3) | 0.055 (3) | 0.058 (3) | −0.011 (2) | −0.018 (2) | −0.005 (3) |
C83 | 0.064 (5) | 0.100 (8) | 0.077 (6) | −0.012 (5) | 0.005 (5) | −0.015 (6) |
C84 | 0.046 (5) | 0.125 (9) | 0.065 (6) | −0.005 (5) | −0.007 (4) | 0.002 (6) |
C85 | 0.128 (9) | 0.115 (9) | 0.083 (7) | −0.066 (7) | −0.075 (7) | 0.076 (7) |
C483 | 0.092 (15) | 0.120 (19) | 0.070 (13) | −0.029 (12) | −0.024 (10) | −0.036 (12) |
C484 | 0.123 (17) | 0.035 (10) | 0.23 (3) | 0.025 (11) | −0.053 (15) | 0.014 (14) |
C485 | 0.083 (13) | 0.30 (3) | 0.051 (6) | −0.048 (16) | −0.013 (6) | 0.035 (19) |
N86 | 0.048 (2) | 0.045 (2) | 0.044 (2) | −0.0033 (16) | 0.0012 (17) | 0.0170 (18) |
C87 | 0.076 (3) | 0.047 (3) | 0.047 (3) | 0.003 (2) | 0.004 (2) | 0.012 (2) |
C88 | 0.086 (7) | 0.172 (12) | 0.039 (5) | 0.017 (7) | 0.004 (5) | −0.024 (6) |
C89 | 0.067 (6) | 0.274 (18) | 0.063 (7) | 0.033 (9) | −0.013 (5) | 0.069 (10) |
C90 | 0.191 (13) | 0.088 (8) | 0.092 (8) | −0.030 (8) | 0.005 (8) | 0.055 (7) |
C488 | 0.148 (17) | 0.077 (16) | 0.078 (15) | 0.019 (12) | 0.024 (14) | 0.016 (13) |
C489 | 0.19 (2) | 0.044 (8) | 0.050 (10) | −0.016 (10) | −0.038 (11) | 0.006 (8) |
C490 | 0.054 (8) | 0.037 (6) | 0.047 (9) | −0.009 (6) | −0.005 (7) | 0.017 (6) |
P1—O2 | 1.481 (3) | C44—H441 | 0.964 |
P1—N3 | 1.646 (4) | C44—H442 | 0.974 |
P1—N6 | 1.639 (3) | C44—H443 | 0.971 |
P1—N11 | 1.629 (3) | C45—H451 | 0.985 |
N3—C4 | 1.447 (5) | C45—H452 | 0.990 |
N3—C5 | 1.452 (6) | C45—H453 | 0.983 |
C4—H41 | 0.960 | P46—O47 | 1.474 (3) |
C4—H42 | 0.963 | P46—N48 | 1.631 (4) |
C4—H43 | 0.962 | P46—N53 | 1.651 (4) |
C5—H51 | 0.968 | P46—N56 | 1.645 (3) |
C5—H52 | 0.960 | N48—H481 | 0.855 |
C5—H53 | 0.960 | N48—C49 | 1.488 (5) |
N6—H61 | 0.858 | C49—C50 | 1.511 (5) |
N6—C7 | 1.485 (5) | C49—C51 | 1.543 (7) |
C7—C8 | 1.534 (6) | C49—C52 | 1.496 (7) |
C7—C9 | 1.520 (7) | C50—H501 | 0.959 |
C7—C10 | 1.506 (7) | C50—H502 | 0.964 |
C8—H81 | 0.961 | C50—H503 | 0.961 |
C8—H82 | 0.956 | C51—H511 | 0.961 |
C8—H83 | 0.963 | C51—H512 | 0.963 |
C9—H91 | 0.965 | C51—H513 | 0.965 |
C9—H92 | 0.959 | C52—H521 | 0.955 |
C9—H93 | 0.962 | C52—H522 | 0.961 |
C10—H101 | 0.962 | C52—H523 | 0.959 |
C10—H102 | 0.964 | N53—C54 | 1.460 (5) |
C10—H103 | 0.963 | N53—C55 | 1.460 (5) |
N11—H111 | 0.852 | C54—H541 | 0.962 |
N11—C12 | 1.469 (4) | C54—H542 | 0.965 |
C12—C13 | 1.485 (8) | C54—H543 | 0.961 |
C12—C14 | 1.499 (8) | C55—H551 | 0.964 |
C12—C15 | 1.572 (8) | C55—H552 | 0.965 |
C12—C413 | 1.519 (7) | C55—H553 | 0.961 |
C12—C414 | 1.475 (8) | N56—H561 | 0.873 |
C12—C415 | 1.585 (8) | N56—C57 | 1.487 (5) |
C13—H131 | 0.964 | C57—C58 | 1.543 (6) |
C13—H132 | 0.966 | C57—C59 | 1.500 (7) |
C13—H133 | 0.968 | C57—C60 | 1.522 (7) |
C14—H141 | 0.958 | C58—H581 | 0.955 |
C14—H142 | 0.957 | C58—H582 | 0.963 |
C14—H143 | 0.961 | C58—H583 | 0.965 |
C15—H151 | 1.027 | C59—H591 | 0.965 |
C15—H152 | 1.029 | C59—H592 | 0.965 |
C15—H153 | 1.037 | C59—H593 | 0.968 |
C413—H4131 | 0.958 | C60—H601 | 0.961 |
C413—H4132 | 0.957 | C60—H602 | 0.967 |
C413—H4133 | 0.955 | C60—H603 | 0.967 |
C414—H4141 | 0.972 | P61—O62 | 1.484 (3) |
C414—H4142 | 0.975 | P61—N63 | 1.644 (4) |
C414—H4143 | 0.978 | P61—N68 | 1.624 (3) |
C415—H4151 | 0.969 | P61—N73 | 1.650 (4) |
C415—H4152 | 0.967 | N63—H631 | 0.862 |
C415—H4153 | 0.974 | N63—C64 | 1.476 (5) |
P16—O17 | 1.472 (3) | C64—C65 | 1.528 (6) |
P16—N18 | 1.635 (4) | C64—C66 | 1.533 (7) |
P16—N21 | 1.641 (3) | C64—C67 | 1.525 (8) |
P16—N26 | 1.645 (3) | C65—H651 | 0.966 |
N18—C19 | 1.460 (6) | C65—H652 | 0.959 |
N18—C20 | 1.438 (6) | C65—H653 | 0.972 |
C19—H191 | 0.965 | C66—H661 | 0.965 |
C19—H192 | 0.964 | C66—H662 | 0.965 |
C19—H193 | 0.954 | C66—H663 | 0.971 |
C20—H201 | 0.966 | C67—H671 | 0.961 |
C20—H202 | 0.956 | C67—H672 | 0.962 |
C20—H203 | 0.960 | C67—H673 | 0.969 |
N21—H211 | 0.853 | N68—H681 | 0.855 |
N21—C22 | 1.485 (5) | N68—C69 | 1.478 (5) |
C22—C23 | 1.533 (6) | C69—C70 | 1.528 (6) |
C22—C24 | 1.520 (7) | C69—C71 | 1.521 (7) |
C22—C25 | 1.519 (7) | C69—C72 | 1.548 (7) |
C23—H231 | 0.963 | C70—H701 | 0.959 |
C23—H232 | 0.966 | C70—H702 | 0.965 |
C23—H233 | 0.965 | C70—H703 | 0.969 |
C24—H241 | 0.967 | C71—H711 | 0.967 |
C24—H242 | 0.965 | C71—H712 | 0.967 |
C24—H243 | 0.963 | C71—H713 | 0.967 |
C25—H251 | 0.971 | C72—H721 | 0.959 |
C25—H252 | 0.965 | C72—H722 | 0.965 |
C25—H253 | 0.963 | C72—H723 | 0.965 |
N26—H261 | 0.864 | N73—C74 | 1.453 (6) |
N26—C27 | 1.478 (4) | N73—C75 | 1.451 (6) |
C27—C28 | 1.552 (6) | C74—H741 | 0.951 |
C27—C29 | 1.492 (5) | C74—H742 | 0.959 |
C27—C30 | 1.530 (5) | C74—H743 | 0.958 |
C27—C428 | 1.556 (9) | C75—H751 | 0.969 |
C27—C429 | 1.510 (10) | C75—H752 | 0.969 |
C27—C430 | 1.523 (10) | C75—H753 | 0.972 |
C28—H281 | 0.962 | P76—O77 | 1.484 (3) |
C28—H282 | 0.957 | P76—N78 | 1.652 (4) |
C28—H283 | 0.961 | P76—N81 | 1.612 (3) |
C29—H291 | 0.960 | P76—N86 | 1.630 (4) |
C29—H292 | 0.962 | N78—C79 | 1.433 (6) |
C29—H293 | 0.963 | N78—C80 | 1.433 (5) |
C30—H301 | 0.963 | C79—H791 | 0.956 |
C30—H302 | 0.959 | C79—H792 | 0.957 |
C30—H303 | 0.963 | C79—H793 | 0.960 |
C428—H4281 | 0.959 | C80—H801 | 0.963 |
C428—H4282 | 0.961 | C80—H802 | 0.970 |
C428—H4283 | 0.962 | C80—H803 | 0.963 |
C429—H4291 | 0.976 | N81—H811 | 0.856 |
C429—H4292 | 0.976 | N81—C82 | 1.476 (4) |
C429—H4293 | 0.976 | C82—C83 | 1.598 (7) |
C430—H4301 | 0.960 | C82—C84 | 1.509 (6) |
C430—H4302 | 0.961 | C82—C85 | 1.485 (7) |
C430—H4303 | 0.960 | C82—C483 | 1.587 (9) |
P31—O32 | 1.481 (3) | C82—C484 | 1.513 (9) |
P31—N33 | 1.636 (3) | C82—C485 | 1.464 (9) |
P31—N38 | 1.642 (3) | C83—H831 | 0.966 |
P31—N43 | 1.640 (4) | C83—H832 | 0.965 |
N33—H331 | 0.854 | C83—H833 | 0.968 |
N33—C34 | 1.463 (4) | C84—H841 | 0.965 |
C34—C35 | 1.492 (6) | C84—H842 | 0.963 |
C34—C36 | 1.490 (7) | C84—H843 | 0.963 |
C34—C37 | 1.554 (7) | C85—H851 | 0.928 |
C34—C435 | 1.474 (9) | C85—H852 | 0.927 |
C34—H4352 | 1.257 | H853—C484 | 1.201 |
C34—C436 | 1.524 (9) | H853—H4842 | 0.644 |
C34—C437 | 1.567 (9) | C483—H4831 | 0.969 |
C35—H351 | 0.956 | C483—H4832 | 0.969 |
C35—H352 | 0.957 | C483—H4833 | 0.970 |
C35—H353 | 0.963 | C484—H4841 | 0.974 |
C36—H362 | 0.961 | C484—H4842 | 0.972 |
C36—H361 | 0.962 | C484—H4843 | 0.970 |
C36—H363 | 0.959 | C485—H4851 | 1.023 |
C37—H371 | 0.968 | C485—H4852 | 1.023 |
C37—H372 | 0.960 | C485—H4853 | 1.016 |
C37—H373 | 0.964 | N86—H861 | 0.852 |
C435—H4351 | 0.968 | N86—C87 | 1.470 (4) |
C435—H4352 | 1.014 | C87—C88 | 1.540 (7) |
C435—H4353 | 0.967 | C87—C89 | 1.421 (7) |
C436—H4361 | 0.961 | C87—C90 | 1.604 (7) |
C436—H4362 | 0.959 | C87—C488 | 1.545 (9) |
C436—H4363 | 0.961 | C87—C489 | 1.446 (9) |
C437—H4371 | 0.969 | C87—C490 | 1.612 (8) |
C437—H4372 | 0.965 | C88—H881 | 0.960 |
C437—H4373 | 0.967 | C88—H882 | 0.961 |
N38—H381 | 0.866 | C88—H883 | 0.966 |
N38—C39 | 1.471 (5) | C89—H891 | 0.966 |
C39—C40 | 1.529 (6) | C89—H892 | 0.964 |
C39—C41 | 1.521 (6) | C89—H893 | 0.966 |
C39—C42 | 1.525 (6) | C90—H901 | 0.964 |
C40—H401 | 0.956 | C90—H902 | 0.963 |
C40—H402 | 0.959 | C90—H903 | 0.962 |
C40—H403 | 0.964 | C488—H4881 | 0.960 |
C41—H411 | 0.957 | C488—H4882 | 1.026 |
C41—H412 | 0.969 | C488—H4883 | 0.964 |
C41—H413 | 0.963 | C489—H4891 | 0.982 |
C42—H421 | 0.965 | C489—H4892 | 0.982 |
C42—H422 | 0.970 | C489—H4893 | 0.984 |
C42—H423 | 0.963 | C490—H4901 | 0.961 |
N43—C44 | 1.442 (6) | C490—H4902 | 0.959 |
N43—C45 | 1.467 (5) | C490—H4903 | 0.959 |
O2—P1—N3 | 106.67 (17) | N43—C44—H441 | 108.4 |
O2—P1—N6 | 115.95 (18) | N43—C44—H442 | 110.5 |
N3—P1—N6 | 110.01 (19) | H441—C44—H442 | 109.5 |
O2—P1—N11 | 117.89 (18) | N43—C44—H443 | 110.2 |
N3—P1—N11 | 106.8 (2) | H441—C44—H443 | 109.2 |
N6—P1—N11 | 99.08 (17) | H442—C44—H443 | 109.1 |
P1—N3—C4 | 123.9 (3) | N43—C45—H451 | 108.3 |
P1—N3—C5 | 121.1 (3) | N43—C45—H452 | 108.6 |
C4—N3—C5 | 113.3 (4) | H451—C45—H452 | 110.8 |
N3—C4—H41 | 110.1 | N43—C45—H453 | 109.1 |
N3—C4—H42 | 109.2 | H451—C45—H453 | 110.2 |
H41—C4—H42 | 109.0 | H452—C45—H453 | 109.9 |
N3—C4—H43 | 109.2 | O47—P46—N48 | 117.44 (17) |
H41—C4—H43 | 110.6 | O47—P46—N53 | 106.71 (17) |
H42—C4—H43 | 108.7 | N48—P46—N53 | 106.44 (19) |
N3—C5—H51 | 110.6 | O47—P46—N56 | 116.76 (18) |
N3—C5—H52 | 109.2 | N48—P46—N56 | 99.03 (17) |
H51—C5—H52 | 108.7 | N53—P46—N56 | 109.93 (19) |
N3—C5—H53 | 109.8 | P46—N48—H481 | 116.4 |
H51—C5—H53 | 109.3 | P46—N48—C49 | 127.7 (3) |
H52—C5—H53 | 109.2 | H481—N48—C49 | 115.5 |
P1—N6—H61 | 115.0 | N48—C49—C50 | 110.8 (3) |
P1—N6—C7 | 126.0 (3) | N48—C49—C51 | 109.9 (4) |
H61—N6—C7 | 115.1 | C50—C49—C51 | 108.8 (4) |
N6—C7—C8 | 105.9 (3) | N48—C49—C52 | 106.9 (4) |
N6—C7—C9 | 110.2 (4) | C50—C49—C52 | 110.5 (4) |
C8—C7—C9 | 109.2 (4) | C51—C49—C52 | 110.0 (4) |
N6—C7—C10 | 110.6 (4) | C49—C50—H501 | 109.2 |
C8—C7—C10 | 109.2 (4) | C49—C50—H502 | 110.3 |
C9—C7—C10 | 111.5 (5) | H501—C50—H502 | 109.8 |
C7—C8—H81 | 109.4 | C49—C50—H503 | 109.9 |
C7—C8—H82 | 109.9 | H501—C50—H503 | 109.3 |
H81—C8—H82 | 110.3 | H502—C50—H503 | 108.4 |
C7—C8—H83 | 109.4 | C49—C51—H511 | 108.9 |
H81—C8—H83 | 109.5 | C49—C51—H512 | 109.2 |
H82—C8—H83 | 108.4 | H511—C51—H512 | 109.9 |
C7—C9—H91 | 109.8 | C49—C51—H513 | 110.2 |
C7—C9—H92 | 109.6 | H511—C51—H513 | 109.2 |
H91—C9—H92 | 108.9 | H512—C51—H513 | 109.5 |
C7—C9—H93 | 109.9 | C49—C52—H521 | 109.7 |
H91—C9—H93 | 109.7 | C49—C52—H522 | 109.0 |
H92—C9—H93 | 108.8 | H521—C52—H522 | 108.9 |
C7—C10—H101 | 110.2 | C49—C52—H523 | 109.1 |
C7—C10—H102 | 109.7 | H521—C52—H523 | 110.7 |
H101—C10—H102 | 109.2 | H522—C52—H523 | 109.5 |
C7—C10—H103 | 109.5 | P46—N53—C54 | 122.9 (3) |
H101—C10—H103 | 108.7 | P46—N53—C55 | 121.0 (3) |
H102—C10—H103 | 109.6 | C54—N53—C55 | 113.0 (4) |
P1—N11—H111 | 115.4 | N53—C54—H541 | 109.7 |
P1—N11—C12 | 128.6 (2) | N53—C54—H542 | 109.9 |
H111—N11—C12 | 115.3 | H541—C54—H542 | 108.6 |
N11—C12—C13 | 113.52 (9) | N53—C54—H543 | 110.3 |
N11—C12—C14 | 108.01 (9) | H541—C54—H543 | 108.9 |
C13—C12—C14 | 112.05 (9) | H542—C54—H543 | 109.5 |
N11—C12—C15 | 105.66 (9) | N53—C55—H551 | 109.9 |
C13—C12—C15 | 107.07 (9) | N53—C55—H552 | 109.6 |
C14—C12—C15 | 110.32 (9) | H551—C55—H552 | 109.8 |
N11—C12—C413 | 113.43 (9) | N53—C55—H553 | 108.9 |
N11—C12—C414 | 108.22 (9) | H551—C55—H553 | 109.4 |
C413—C12—C414 | 112.03 (9) | H552—C55—H553 | 109.3 |
N11—C12—C415 | 105.60 (9) | P46—N56—H561 | 116.0 |
C413—C12—C415 | 106.92 (9) | P46—N56—C57 | 124.9 (3) |
C414—C12—C415 | 110.44 (9) | H561—N56—C57 | 116.3 |
C12—C13—H131 | 109.6 | N56—C57—C58 | 106.0 (4) |
C12—C13—H132 | 109.0 | N56—C57—C59 | 110.5 (4) |
H131—C13—H132 | 109.5 | C58—C57—C59 | 109.7 (4) |
C12—C13—H133 | 109.0 | N56—C57—C60 | 109.9 (4) |
H131—C13—H133 | 109.8 | C58—C57—C60 | 109.5 (4) |
H132—C13—H133 | 109.9 | C59—C57—C60 | 111.1 (5) |
C12—C14—H141 | 110.7 | C57—C58—H581 | 110.2 |
C12—C14—H142 | 109.5 | C57—C58—H582 | 110.5 |
H141—C14—H142 | 109.0 | H581—C58—H582 | 108.8 |
C12—C14—H143 | 109.6 | C57—C58—H583 | 109.3 |
H141—C14—H143 | 108.9 | H581—C58—H583 | 109.0 |
H142—C14—H143 | 109.1 | H582—C58—H583 | 109.0 |
C12—C15—H151 | 106.9 | C57—C59—H591 | 109.4 |
C12—C15—H152 | 106.3 | C57—C59—H592 | 108.2 |
H151—C15—H152 | 111.4 | H591—C59—H592 | 110.0 |
C12—C15—H153 | 108.1 | C57—C59—H593 | 109.6 |
H151—C15—H153 | 111.9 | H591—C59—H593 | 110.0 |
H152—C15—H153 | 111.9 | H592—C59—H593 | 109.6 |
C12—C413—H4131 | 110.3 | C57—C60—H601 | 110.0 |
C12—C413—H4132 | 110.4 | C57—C60—H602 | 109.3 |
H4131—C413—H4132 | 108.7 | H601—C60—H602 | 109.4 |
C12—C413—H4133 | 109.2 | C57—C60—H603 | 109.4 |
H4131—C413—H4133 | 109.4 | H601—C60—H603 | 109.0 |
H4132—C413—H4133 | 108.8 | H602—C60—H603 | 109.7 |
C12—C414—H4141 | 107.9 | O62—P61—N63 | 117.21 (18) |
C12—C414—H4142 | 108.5 | O62—P61—N68 | 118.09 (18) |
H4141—C414—H4142 | 109.6 | N63—P61—N68 | 99.12 (17) |
C12—C414—H4143 | 110.2 | O62—P61—N73 | 107.09 (19) |
H4141—C414—H4143 | 110.2 | N63—P61—N73 | 107.6 (2) |
H4142—C414—H4143 | 110.5 | N68—P61—N73 | 107.0 (2) |
C12—C415—H4151 | 110.2 | P61—N63—H631 | 115.4 |
C12—C415—H4152 | 109.0 | P61—N63—C64 | 124.7 (3) |
H4151—C415—H4152 | 109.3 | H631—N63—C64 | 115.6 |
C12—C415—H4153 | 108.9 | N63—C64—C65 | 107.6 (4) |
H4151—C415—H4153 | 110.2 | N63—C64—C66 | 110.5 (4) |
H4152—C415—H4153 | 109.2 | C65—C64—C66 | 109.2 (5) |
O17—P16—N18 | 106.97 (18) | N63—C64—C67 | 110.1 (4) |
O17—P16—N21 | 117.46 (19) | C65—C64—C67 | 109.5 (4) |
N18—P16—N21 | 108.2 (2) | C66—C64—C67 | 110.0 (5) |
O17—P16—N26 | 116.42 (19) | C64—C65—H651 | 108.7 |
N18—P16—N26 | 107.7 (2) | C64—C65—H652 | 110.0 |
N21—P16—N26 | 99.50 (17) | H651—C65—H652 | 109.0 |
P16—N18—C19 | 121.2 (3) | C64—C65—H653 | 110.0 |
P16—N18—C20 | 125.9 (4) | H651—C65—H653 | 109.6 |
C19—N18—C20 | 112.9 (4) | H652—C65—H653 | 109.5 |
N18—C19—H191 | 109.8 | C64—C66—H661 | 110.3 |
N18—C19—H192 | 109.8 | C64—C66—H662 | 110.1 |
H191—C19—H192 | 109.9 | H661—C66—H662 | 109.3 |
N18—C19—H193 | 108.6 | C64—C66—H663 | 108.9 |
H191—C19—H193 | 110.0 | H661—C66—H663 | 108.8 |
H192—C19—H193 | 108.8 | H662—C66—H663 | 109.4 |
N18—C20—H201 | 110.6 | C64—C67—H671 | 108.7 |
N18—C20—H202 | 110.3 | C64—C67—H672 | 108.8 |
H201—C20—H202 | 109.1 | H671—C67—H672 | 110.1 |
N18—C20—H203 | 108.2 | C64—C67—H673 | 109.5 |
H201—C20—H203 | 109.6 | H671—C67—H673 | 109.8 |
H202—C20—H203 | 108.9 | H672—C67—H673 | 109.9 |
P16—N21—H211 | 115.4 | P61—N68—H681 | 114.2 |
P16—N21—C22 | 126.0 (3) | P61—N68—C69 | 126.9 (3) |
H211—N21—C22 | 115.7 | H681—N68—C69 | 113.9 |
N21—C22—C23 | 106.2 (4) | N68—C69—C70 | 107.4 (4) |
N21—C22—C24 | 110.0 (4) | N68—C69—C71 | 110.9 (4) |
C23—C22—C24 | 110.5 (4) | C70—C69—C71 | 111.6 (4) |
N21—C22—C25 | 111.3 (4) | N68—C69—C72 | 110.0 (4) |
C23—C22—C25 | 109.6 (4) | C70—C69—C72 | 108.4 (4) |
C24—C22—C25 | 109.1 (4) | C71—C69—C72 | 108.5 (4) |
C22—C23—H231 | 109.6 | C69—C70—H701 | 110.7 |
C22—C23—H232 | 109.1 | C69—C70—H702 | 110.2 |
H231—C23—H232 | 109.9 | H701—C70—H702 | 108.6 |
C22—C23—H233 | 108.9 | C69—C70—H703 | 110.7 |
H231—C23—H233 | 109.3 | H701—C70—H703 | 107.4 |
H232—C23—H233 | 110.1 | H702—C70—H703 | 109.1 |
C22—C24—H241 | 109.9 | C69—C71—H711 | 108.8 |
C22—C24—H242 | 109.1 | C69—C71—H712 | 110.4 |
H241—C24—H242 | 109.2 | H711—C71—H712 | 109.7 |
C22—C24—H243 | 109.2 | C69—C71—H713 | 109.0 |
H241—C24—H243 | 110.1 | H711—C71—H713 | 109.0 |
H242—C24—H243 | 109.3 | H712—C71—H713 | 109.9 |
C22—C25—H251 | 109.4 | C69—C72—H721 | 109.4 |
C22—C25—H252 | 109.9 | C69—C72—H722 | 109.5 |
H251—C25—H252 | 109.8 | H721—C72—H722 | 109.7 |
C22—C25—H253 | 108.9 | C69—C72—H723 | 109.4 |
H251—C25—H253 | 109.1 | H721—C72—H723 | 110.0 |
H252—C25—H253 | 109.7 | H722—C72—H723 | 108.8 |
P16—N26—H261 | 115.6 | P61—N73—C74 | 120.3 (3) |
P16—N26—C27 | 126.0 (2) | P61—N73—C75 | 125.7 (4) |
H261—N26—C27 | 116.1 | C74—N73—C75 | 113.9 (4) |
N26—C27—C28 | 111.24 (9) | N73—C74—H741 | 110.7 |
N26—C27—C29 | 108.95 (9) | N73—C74—H742 | 110.1 |
C28—C27—C29 | 110.61 (9) | H741—C74—H742 | 109.7 |
N26—C27—C30 | 107.60 (9) | N73—C74—H743 | 109.1 |
C28—C27—C30 | 106.46 (9) | H741—C74—H743 | 108.7 |
C29—C27—C30 | 111.93 (9) | H742—C74—H743 | 108.4 |
N26—C27—C428 | 111.31 (9) | N73—C75—H751 | 109.8 |
N26—C27—C429 | 108.93 (9) | N73—C75—H752 | 110.2 |
C428—C27—C429 | 110.60 (9) | H751—C75—H752 | 109.6 |
N26—C27—C430 | 107.55 (9) | N73—C75—H753 | 108.8 |
C428—C27—C430 | 106.47 (9) | H751—C75—H753 | 108.7 |
C429—C27—C430 | 111.95 (9) | H752—C75—H753 | 109.7 |
C27—C28—H281 | 110.2 | O77—P76—N78 | 106.81 (17) |
C27—C28—H282 | 109.3 | O77—P76—N81 | 116.69 (18) |
H281—C28—H282 | 109.0 | N78—P76—N81 | 107.4 (2) |
C27—C28—H283 | 110.2 | O77—P76—N86 | 116.79 (18) |
H281—C28—H283 | 108.9 | N78—P76—N86 | 108.8 (2) |
H282—C28—H283 | 109.2 | N81—P76—N86 | 99.87 (16) |
C27—C29—H291 | 110.1 | P76—N78—C79 | 123.4 (3) |
C27—C29—H292 | 109.2 | P76—N78—C80 | 122.5 (3) |
H291—C29—H292 | 109.5 | C79—N78—C80 | 114.1 (4) |
C27—C29—H293 | 109.6 | N78—C79—H791 | 109.2 |
H291—C29—H293 | 109.7 | N78—C79—H792 | 109.3 |
H292—C29—H293 | 108.7 | H791—C79—H792 | 110.4 |
C27—C30—H301 | 109.7 | N78—C79—H793 | 109.1 |
C27—C30—H302 | 109.2 | H791—C79—H793 | 109.5 |
H301—C30—H302 | 109.4 | H792—C79—H793 | 109.2 |
C27—C30—H303 | 109.0 | N78—C80—H801 | 109.0 |
H301—C30—H303 | 110.3 | N78—C80—H802 | 108.2 |
H302—C30—H303 | 109.2 | H801—C80—H802 | 111.2 |
C27—C428—H4281 | 108.8 | N78—C80—H803 | 108.7 |
C27—C428—H4282 | 110.8 | H801—C80—H803 | 109.2 |
H4281—C428—H4282 | 109.5 | H802—C80—H803 | 110.5 |
C27—C428—H4283 | 109.1 | P76—N81—H811 | 114.9 |
H4281—C428—H4283 | 109.3 | P76—N81—C82 | 131.0 (2) |
H4282—C428—H4283 | 109.4 | H811—N81—C82 | 113.7 |
C27—C429—H4291 | 109.2 | N81—C82—C83 | 106.16 (9) |
C27—C429—H4292 | 109.3 | N81—C82—C84 | 111.36 (9) |
H4291—C429—H4292 | 109.8 | C83—C82—C84 | 103.86 (9) |
C27—C429—H4293 | 109.3 | N81—C82—C85 | 111.45 (9) |
H4291—C429—H4293 | 109.8 | C83—C82—C85 | 105.91 (9) |
H4292—C429—H4293 | 109.6 | C84—C82—C85 | 117.07 (9) |
C27—C430—H4301 | 109.4 | N81—C82—C483 | 106.29 (9) |
C27—C430—H4302 | 108.8 | N81—C82—C484 | 111.11 (9) |
H4301—C430—H4302 | 109.6 | C483—C82—C484 | 103.86 (9) |
C27—C430—H4303 | 110.0 | N81—C82—C485 | 111.50 (9) |
H4301—C430—H4303 | 109.7 | C483—C82—C485 | 106.02 (9) |
H4302—C430—H4303 | 109.3 | C484—C82—C485 | 117.07 (9) |
O32—P31—N33 | 116.98 (17) | C82—C83—H831 | 109.9 |
O32—P31—N38 | 117.15 (17) | C82—C83—H832 | 109.9 |
N33—P31—N38 | 99.41 (17) | H831—C83—H832 | 110.0 |
O32—P31—N43 | 105.90 (18) | C82—C83—H833 | 108.1 |
N33—P31—N43 | 108.7 (2) | H831—C83—H833 | 109.3 |
N38—P31—N43 | 108.34 (19) | H832—C83—H833 | 109.5 |
P31—N33—H331 | 114.8 | C82—C84—H841 | 108.9 |
P31—N33—C34 | 127.1 (2) | C82—C84—H842 | 109.6 |
H331—N33—C34 | 116.7 | H841—C84—H842 | 109.6 |
N33—C34—C35 | 115.24 (9) | C82—C84—H843 | 110.1 |
N33—C34—C36 | 108.99 (9) | H841—C84—H843 | 109.3 |
C35—C34—C36 | 113.12 (9) | H842—C84—H843 | 109.4 |
N33—C34—C37 | 105.43 (9) | C82—C85—H851 | 121.3 |
C35—C34—C37 | 106.20 (9) | C82—C85—H852 | 119.2 |
C36—C34—C37 | 107.24 (9) | H851—C85—H852 | 117.3 |
N33—C34—C435 | 115.33 (9) | C484—H853—H4842 | 53.9 |
N33—C34—H4352 | 117.0 | C82—C483—H4831 | 110.8 |
N33—C34—C436 | 108.77 (9) | C82—C483—H4832 | 106.5 |
C435—C34—C436 | 113.10 (9) | H4831—C483—H4832 | 110.0 |
N33—C34—C437 | 105.49 (9) | C82—C483—H4833 | 110.1 |
C435—C34—C437 | 106.37 (9) | H4831—C483—H4833 | 109.4 |
H4352—C34—C437 | 135.0 | H4832—C483—H4833 | 110.0 |
C436—C34—C437 | 107.16 (9) | C82—C484—H853 | 98.6 |
C34—C35—H351 | 110.1 | C82—C484—H4841 | 107.8 |
C34—C35—H352 | 110.3 | H853—C484—H4841 | 141.4 |
H351—C35—H352 | 108.9 | C82—C484—H4842 | 112.6 |
C34—C35—H353 | 108.8 | H4841—C484—H4842 | 109.7 |
H351—C35—H353 | 109.5 | C82—C484—H4843 | 108.1 |
H352—C35—H353 | 109.2 | H4841—C484—H4843 | 109.6 |
C34—C36—H362 | 108.3 | H4842—C484—H4843 | 109.0 |
C34—C36—H361 | 110.8 | C82—C485—H4851 | 106.3 |
H362—C36—H361 | 109.6 | C82—C485—H4852 | 104.5 |
C34—C36—H363 | 108.7 | H4851—C485—H4852 | 111.1 |
H362—C36—H363 | 109.7 | C82—C485—H4853 | 111.1 |
H361—C36—H363 | 109.7 | H4851—C485—H4853 | 111.9 |
C34—C37—H371 | 109.1 | H4852—C485—H4853 | 111.5 |
C34—C37—H372 | 108.4 | P76—N86—H861 | 115.4 |
H371—C37—H372 | 109.1 | P76—N86—C87 | 129.5 (2) |
C34—C37—H373 | 110.6 | H861—N86—C87 | 113.3 |
H371—C37—H373 | 109.8 | N86—C87—C88 | 109.76 (9) |
H372—C37—H373 | 109.8 | N86—C87—C89 | 110.04 (9) |
C34—C435—H4351 | 115.8 | C88—C87—C89 | 114.63 (9) |
H4351—C435—H4352 | 115.4 | N86—C87—C90 | 107.21 (9) |
C34—C435—H4353 | 116.2 | C88—C87—C90 | 103.49 (9) |
H4351—C435—H4353 | 120.4 | C89—C87—C90 | 111.31 (9) |
H4352—C435—H4353 | 116.1 | N86—C87—C488 | 109.95 (9) |
C34—C436—H4361 | 109.4 | N86—C87—H4882 | 112.1 |
C34—C436—H4362 | 109.2 | N86—C87—C489 | 109.99 (9) |
H4361—C436—H4362 | 109.4 | C488—C87—C489 | 114.70 (9) |
C34—C436—H4363 | 110.6 | N86—C87—C490 | 107.08 (9) |
H4361—C436—H4363 | 109.4 | C488—C87—C490 | 103.57 (9) |
H4362—C436—H4363 | 108.8 | C489—C87—C490 | 111.15 (9) |
C34—C437—H4371 | 108.8 | C87—C88—H881 | 110.1 |
C34—C437—H4372 | 109.1 | C87—C88—H882 | 109.8 |
H4371—C437—H4372 | 109.6 | H881—C88—H882 | 109.0 |
C34—C437—H4373 | 110.0 | C87—C88—H883 | 109.9 |
H4371—C437—H4373 | 109.7 | H881—C88—H883 | 109.1 |
H4372—C437—H4373 | 109.6 | H882—C88—H883 | 109.0 |
P31—N38—H381 | 114.5 | C87—C89—H891 | 108.1 |
P31—N38—C39 | 126.6 (3) | C87—C89—H892 | 112.5 |
H381—N38—C39 | 115.5 | H891—C89—H892 | 110.3 |
N38—C39—C40 | 110.9 (3) | C87—C89—H893 | 107.6 |
N38—C39—C41 | 109.6 (4) | H891—C89—H893 | 109.1 |
C40—C39—C41 | 109.3 (4) | H892—C89—H893 | 109.1 |
N38—C39—C42 | 106.3 (3) | C87—C90—H901 | 109.8 |
C40—C39—C42 | 111.3 (4) | C87—C90—H902 | 108.2 |
C41—C39—C42 | 109.5 (4) | H901—C90—H902 | 109.8 |
C39—C40—H401 | 108.6 | C87—C90—H903 | 110.0 |
C39—C40—H402 | 109.5 | H901—C90—H903 | 109.4 |
H401—C40—H402 | 109.8 | H902—C90—H903 | 109.7 |
C39—C40—H403 | 109.8 | C87—C488—H4881 | 109.0 |
H401—C40—H403 | 109.3 | H4881—C488—H4882 | 119.4 |
H402—C40—H403 | 109.8 | C87—C488—H4883 | 108.9 |
C39—C41—H411 | 109.9 | H4881—C488—H4883 | 120.3 |
C39—C41—H412 | 109.7 | H4882—C488—H4883 | 119.7 |
H411—C41—H412 | 109.5 | C87—C489—H4891 | 107.5 |
C39—C41—H413 | 109.8 | C87—C489—H4892 | 114.4 |
H411—C41—H413 | 109.2 | H4891—C489—H4892 | 109.4 |
H412—C41—H413 | 108.7 | C87—C489—H4893 | 105.5 |
C39—C42—H421 | 109.8 | H4891—C489—H4893 | 110.1 |
C39—C42—H422 | 109.2 | H4892—C489—H4893 | 109.9 |
H421—C42—H422 | 109.6 | C87—C490—H4901 | 109.0 |
C39—C42—H423 | 110.0 | C87—C490—H4902 | 108.0 |
H421—C42—H423 | 109.3 | H4901—C490—H4902 | 109.4 |
H422—C42—H423 | 108.9 | C87—C490—H4903 | 111.8 |
P31—N43—C44 | 123.7 (3) | H4901—C490—H4903 | 109.8 |
P31—N43—C45 | 121.1 (3) | H4902—C490—H4903 | 108.9 |
C44—N43—C45 | 115.2 (4) | ||
O77—P76—N78—C79 | 0.2 (5) | N56—P46—N53—C54 | 118.0 (4) |
O77—P76—N78—C80 | −176.8 (4) | O47—P46—N53—C54 | −9.5 (4) |
N81—P76—N78—C79 | −125.8 (5) | O47—P46—N53—C55 | −168.1 (3) |
N81—P76—N78—C80 | 57.3 (5) | N56—P46—N48—C49 | 169.5 (3) |
N86—P76—N78—C79 | 127.0 (5) | O47—P46—N48—C49 | −63.9 (4) |
N86—P76—N78—C80 | −49.9 (5) | N53—P46—N48—C49 | 55.5 (4) |
O77—P76—N81—C82 | −52.4 (4) | N73—P61—N68—C69 | −78.6 (4) |
N78—P76—N81—C82 | 67.4 (4) | O62—P61—N68—C69 | 42.2 (4) |
N86—P76—N81—C82 | −179.2 (3) | O62—P61—N73—C74 | −177.7 (4) |
O77—P76—N86—C87 | 45.9 (4) | N63—P61—N73—C74 | 55.5 (4) |
N78—P76—N86—C87 | −75.0 (4) | N63—P61—N73—C75 | −123.0 (4) |
N81—P76—N86—C87 | 172.7 (3) | N63—P61—N68—C69 | 169.8 (4) |
O2—P1—N11—C12 | −58.9 (4) | N68—P61—N73—C75 | 131.4 (4) |
N3—P1—N11—C12 | 60.9 (4) | N73—P61—N63—C64 | 78.0 (4) |
N6—P1—N11—C12 | 175.2 (3) | O62—P61—N63—C64 | −42.7 (4) |
N11—P1—N3—C4 | −134.0 (4) | N68—P61—N73—C74 | −50.2 (4) |
N11—P1—N3—C5 | 61.9 (5) | N68—P61—N63—C64 | −170.9 (4) |
O2—P1—N6—C7 | 38.3 (4) | O62—P61—N73—C75 | 3.9 (5) |
O2—P1—N3—C4 | −7.1 (5) | P76—N81—C82—C84 | 19.3 (6) |
O2—P1—N3—C5 | −171.3 (5) | P76—N81—C82—C85 | 152.0 (4) |
N6—P1—N3—C4 | 119.4 (4) | P76—N81—C82—C83 | −93.1 (4) |
N6—P1—N3—C5 | −44.8 (5) | P76—N86—C87—C88 | −75.0 (5) |
N3—P1—N6—C7 | −82.8 (4) | P76—N86—C87—C90 | 36.8 (5) |
N11—P1—N6—C7 | 165.5 (4) | P76—N86—C87—C89 | 158.0 (4) |
N21—P16—N18—C19 | −49.4 (5) | P1—N6—C7—C10 | −79.4 (5) |
N18—P16—N26—C27 | 75.3 (3) | P1—N6—C7—C9 | 44.4 (5) |
N21—P16—N26—C27 | −172.0 (3) | P1—N6—C7—C8 | 162.3 (3) |
N18—P16—N21—C22 | −74.9 (4) | P1—N11—C12—C413 | 21.7 (6) |
N26—P16—N21—C22 | 172.8 (4) | P1—N11—C12—C415 | −95.1 (4) |
O17—P16—N26—C27 | −44.8 (4) | P1—N11—C12—C414 | 146.7 (4) |
O17—P16—N18—C20 | 4.2 (6) | P16—N21—C22—C24 | −81.2 (5) |
N26—P16—N18—C20 | −121.6 (5) | P16—N21—C22—C25 | 40.0 (5) |
N21—P16—N18—C20 | 131.7 (5) | P16—N21—C22—C23 | 159.2 (3) |
N26—P16—N18—C19 | 57.3 (4) | P16—N26—C27—C30 | −156.1 (3) |
O17—P16—N21—C22 | 46.3 (4) | P16—N26—C27—C28 | −39.9 (4) |
O17—P16—N18—C19 | −176.8 (4) | P16—N26—C27—C29 | 82.3 (4) |
N33—P31—N43—C45 | 58.0 (4) | P31—N33—C34—C37 | 106.7 (5) |
O32—P31—N43—C45 | −175.5 (4) | P31—N33—C34—C35 | −10.0 (5) |
N33—P31—N43—C44 | −121.5 (4) | P31—N33—C34—C36 | −138.4 (4) |
N43—P31—N33—C34 | 63.6 (4) | P31—N38—C39—C41 | 48.7 (5) |
N38—P31—N43—C44 | 131.4 (4) | P31—N38—C39—C42 | 167.0 (3) |
N38—P31—N43—C45 | −49.0 (4) | P31—N38—C39—C40 | −72.0 (4) |
O32—P31—N43—C44 | 4.9 (4) | P46—N48—C49—C50 | 31.7 (5) |
N33—P31—N38—C39 | 166.7 (3) | P46—N48—C49—C52 | 152.1 (4) |
N43—P31—N38—C39 | −80.0 (4) | P46—N48—C49—C51 | −88.6 (4) |
N38—P31—N33—C34 | 176.7 (3) | P46—N56—C57—C59 | −79.0 (5) |
O32—P31—N33—C34 | −56.2 (4) | P46—N56—C57—C60 | 44.1 (5) |
O32—P31—N38—C39 | 39.6 (4) | P46—N56—C57—C58 | 162.2 (3) |
N48—P46—N53—C55 | 65.8 (4) | P61—N63—C64—C65 | −165.3 (4) |
N56—P46—N53—C55 | −40.6 (4) | P61—N63—C64—C66 | 75.8 (5) |
O47—P46—N56—C57 | 38.6 (4) | P61—N63—C64—C67 | −45.9 (5) |
N48—P46—N56—C57 | 165.7 (3) | P61—N68—C69—C70 | 159.1 (3) |
N53—P46—N56—C57 | −83.1 (4) | P61—N68—C69—C71 | −78.7 (5) |
N48—P46—N53—C54 | −135.7 (3) | P61—N68—C69—C72 | 41.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H61···O77 | 0.86 | 2.10 | 2.937 (9) | 165 |
N11—H111···O77 | 0.85 | 2.08 | 2.911 (9) | 164 |
N21—H211···O62 | 0.85 | 2.21 | 3.038 (9) | 162 |
N26—H261···O62 | 0.86 | 2.11 | 2.952 (9) | 166 |
N33—H331···O17 | 0.85 | 2.10 | 2.943 (9) | 167 |
N38—H381···O17 | 0.87 | 2.22 | 3.046 (9) | 159 |
N48—H481···O2 | 0.86 | 2.16 | 2.981 (9) | 161 |
N56—H561···O2 | 0.87 | 2.10 | 2.931 (9) | 158 |
N63—H631···O32i | 0.86 | 2.17 | 2.994 (9) | 160 |
N68—H681···O32i | 0.86 | 2.04 | 2.884 (9) | 168 |
N81—H811···O47i | 0.86 | 2.09 | 2.927 (9) | 166 |
N86—H861···O47i | 0.85 | 2.16 | 2.986 (9) | 163 |
Symmetry code: (i) x+1, y, z. |
C16H40N4O3P2 | F(000) = 872 |
Mr = 398.5 | Dx = 1.097 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 9398 reflections |
a = 11.3715 (4) Å | θ = 3.7–67.1° |
b = 17.7755 (7) Å | µ = 1.80 mm−1 |
c = 13.6956 (5) Å | T = 150 K |
β = 119.371 (4)° | Prism, colourless |
V = 2412.51 (18) Å3 | 0.37 × 0.22 × 0.09 mm |
Z = 4 |
Gemini Ultra diffractometer with Atlas detector | 4265 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray Source | 3420 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3784 pixels mm-1 | θmax = 67.2°, θmin = 4.5° |
Rotation method data acquisition using ω scans | h = −13→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −21→21 |
Tmin = 0.746, Tmax = 1.000 | l = −12→16 |
15622 measured reflections |
Refinement on F2 | 148 constraints |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
S = 1.60 | (Δ/σ)max = 0.002 |
4265 reflections | Δρmax = 0.33 e Å−3 |
238 parameters | Δρmin = −0.21 e Å−3 |
4 restraints |
C16H40N4O3P2 | V = 2412.51 (18) Å3 |
Mr = 398.5 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 11.3715 (4) Å | µ = 1.80 mm−1 |
b = 17.7755 (7) Å | T = 150 K |
c = 13.6956 (5) Å | 0.37 × 0.22 × 0.09 mm |
β = 119.371 (4)° |
Gemini Ultra diffractometer with Atlas detector | 4265 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 3420 reflections with I > 3σ(I) |
Tmin = 0.746, Tmax = 1.000 | Rint = 0.033 |
15622 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 4 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.60 | Δρmax = 0.33 e Å−3 |
4265 reflections | Δρmin = −0.21 e Å−3 |
238 parameters |
Experimental. Absorption correction: CrysAlis PRO (Agilent, 2010), multi-scan using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.27512 (5) | 0.23253 (3) | 0.54865 (4) | 0.02780 (19) | |
P2 | 0.12827 (4) | 0.24723 (2) | 0.67070 (4) | 0.02659 (18) | |
O1 | 0.21004 (12) | 0.28033 (7) | 0.61111 (9) | 0.0287 (5) | |
O2 | 0.17179 (13) | 0.18682 (7) | 0.45603 (10) | 0.0339 (5) | |
O3 | 0.21375 (13) | 0.19473 (7) | 0.76223 (10) | 0.0315 (5) | |
N1 | 0.39326 (16) | 0.18678 (8) | 0.65511 (12) | 0.0311 (6) | |
N2 | 0.33956 (16) | 0.29241 (9) | 0.50011 (12) | 0.0317 (6) | |
N3 | −0.00300 (16) | 0.21182 (9) | 0.56138 (12) | 0.0309 (6) | |
N4 | 0.08569 (16) | 0.31779 (9) | 0.71999 (12) | 0.0320 (6) | |
C1 | 0.4652 (2) | 0.11921 (11) | 0.64637 (18) | 0.0398 (9) | |
C2 | 0.4887 (3) | 0.12659 (14) | 0.54571 (19) | 0.0503 (10) | |
C3 | 0.6012 (2) | 0.11542 (15) | 0.7536 (2) | 0.0540 (11) | |
C4 | 0.3821 (3) | 0.04932 (13) | 0.6338 (3) | 0.0644 (15) | |
C5 | 0.4264 (2) | 0.35926 (11) | 0.55199 (16) | 0.0389 (8) | |
C6 | 0.5158 (3) | 0.36650 (18) | 0.4992 (2) | 0.0685 (13) | |
C7 | 0.5122 (3) | 0.35142 (15) | 0.67740 (19) | 0.0676 (12) | |
C8 | 0.3361 (3) | 0.42794 (14) | 0.5241 (3) | 0.0700 (15) | |
C9 | −0.0964 (2) | 0.15571 (11) | 0.56689 (17) | 0.0385 (8) | |
C10 | −0.0349 (3) | 0.07749 (13) | 0.5816 (2) | 0.0573 (13) | |
C11 | −0.2274 (2) | 0.16068 (16) | 0.4558 (2) | 0.0576 (11) | |
C12 | −0.1228 (3) | 0.17341 (14) | 0.6630 (2) | 0.0521 (11) | |
C13 | 0.0167 (2) | 0.39025 (10) | 0.67141 (16) | 0.0374 (8) | |
C14 | 0.1236 (3) | 0.45200 (12) | 0.7124 (2) | 0.0553 (12) | |
C15 | −0.0599 (3) | 0.38826 (13) | 0.54431 (18) | 0.0570 (11) | |
C16 | −0.0804 (2) | 0.40471 (13) | 0.7163 (2) | 0.0500 (10) | |
H2A | 0.536663 | 0.083219 | 0.541987 | 0.0755* | |
H2B | 0.403379 | 0.130142 | 0.478089 | 0.0755* | |
H2C | 0.540807 | 0.17102 | 0.554029 | 0.0755* | |
H3A | 0.64934 | 0.071562 | 0.751895 | 0.0811* | |
H3B | 0.652744 | 0.159607 | 0.759448 | 0.0811* | |
H3C | 0.58698 | 0.112714 | 0.817128 | 0.0811* | |
H4A | 0.429869 | 0.005632 | 0.630805 | 0.0966* | |
H4B | 0.366912 | 0.045378 | 0.696632 | 0.0966* | |
H4C | 0.296994 | 0.052766 | 0.565929 | 0.0966* | |
H6A | 0.573391 | 0.409562 | 0.529847 | 0.1028* | |
H6B | 0.569966 | 0.322031 | 0.514682 | 0.1028* | |
H6C | 0.460612 | 0.372506 | 0.419656 | 0.1028* | |
H7A | 0.565508 | 0.396044 | 0.707602 | 0.1014* | |
H7B | 0.455052 | 0.344532 | 0.709999 | 0.1014* | |
H7C | 0.570719 | 0.308696 | 0.694377 | 0.1014* | |
H8A | 0.390318 | 0.471454 | 0.559717 | 0.1051* | |
H8B | 0.288099 | 0.435323 | 0.444383 | 0.1051* | |
H8C | 0.272749 | 0.420479 | 0.550417 | 0.1051* | |
H10A | −0.097897 | 0.040561 | 0.579181 | 0.0859* | |
H10B | −0.014774 | 0.067959 | 0.522367 | 0.0859* | |
H10C | 0.04658 | 0.074707 | 0.652494 | 0.0859* | |
H11A | −0.291317 | 0.125306 | 0.455592 | 0.0864* | |
H11B | −0.263473 | 0.210643 | 0.446218 | 0.0864* | |
H11C | −0.209998 | 0.149209 | 0.395554 | 0.0864* | |
H12A | −0.18516 | 0.137383 | 0.663884 | 0.0782* | |
H12B | −0.039497 | 0.171006 | 0.732647 | 0.0782* | |
H12C | −0.160292 | 0.223011 | 0.653342 | 0.0782* | |
H14A | 0.080699 | 0.499832 | 0.685089 | 0.0829* | |
H14B | 0.171832 | 0.452536 | 0.792812 | 0.0829* | |
H14C | 0.185395 | 0.442476 | 0.685041 | 0.0829* | |
H15A | −0.105001 | 0.435449 | 0.516157 | 0.0855* | |
H15B | 0.002222 | 0.379645 | 0.516961 | 0.0855* | |
H15C | −0.125242 | 0.34843 | 0.51941 | 0.0855* | |
H16A | −0.122602 | 0.452877 | 0.690585 | 0.0751* | |
H16B | −0.148216 | 0.366164 | 0.689761 | 0.0751* | |
H16C | −0.031419 | 0.404193 | 0.796687 | 0.0751* | |
H1N | 0.375 (2) | 0.1808 (12) | 0.7090 (14) | 0.0373* | |
H2N | 0.298 (2) | 0.2962 (12) | 0.4276 (8) | 0.038* | |
H3N | 0.015 (2) | 0.1989 (12) | 0.5088 (14) | 0.0371* | |
H4N | 0.116 (2) | 0.3165 (13) | 0.7917 (9) | 0.0384* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0304 (2) | 0.0325 (2) | 0.0193 (2) | −0.00433 (17) | 0.01126 (19) | −0.00167 (16) |
P2 | 0.0287 (2) | 0.0304 (2) | 0.0181 (2) | 0.00091 (17) | 0.00953 (19) | 0.00071 (16) |
O1 | 0.0312 (6) | 0.0319 (6) | 0.0197 (6) | −0.0012 (5) | 0.0100 (5) | −0.0001 (5) |
O2 | 0.0382 (7) | 0.0402 (7) | 0.0241 (6) | −0.0110 (6) | 0.0158 (6) | −0.0067 (5) |
O3 | 0.0369 (7) | 0.0343 (6) | 0.0212 (6) | 0.0061 (5) | 0.0126 (5) | 0.0033 (5) |
N1 | 0.0362 (8) | 0.0331 (8) | 0.0259 (8) | 0.0034 (6) | 0.0166 (7) | 0.0023 (6) |
N2 | 0.0347 (8) | 0.0393 (8) | 0.0171 (7) | −0.0097 (7) | 0.0097 (6) | −0.0014 (6) |
N3 | 0.0317 (8) | 0.0370 (8) | 0.0234 (8) | −0.0054 (6) | 0.0131 (6) | −0.0027 (6) |
N4 | 0.0363 (8) | 0.0353 (8) | 0.0195 (7) | 0.0068 (7) | 0.0099 (7) | 0.0028 (6) |
C1 | 0.0443 (11) | 0.0381 (10) | 0.0427 (12) | 0.0074 (8) | 0.0257 (10) | 0.0026 (8) |
C2 | 0.0556 (14) | 0.0560 (13) | 0.0458 (13) | 0.0093 (11) | 0.0300 (11) | −0.0034 (10) |
C3 | 0.0503 (13) | 0.0684 (15) | 0.0452 (13) | 0.0245 (12) | 0.0248 (11) | 0.0131 (11) |
C4 | 0.0758 (18) | 0.0363 (11) | 0.096 (2) | 0.0005 (11) | 0.0537 (17) | −0.0013 (12) |
C5 | 0.0433 (11) | 0.0373 (10) | 0.0282 (10) | −0.0144 (8) | 0.0115 (9) | −0.0007 (8) |
C6 | 0.0612 (16) | 0.0857 (19) | 0.0644 (17) | −0.0396 (15) | 0.0352 (14) | −0.0163 (14) |
C7 | 0.0816 (19) | 0.0660 (16) | 0.0291 (12) | −0.0428 (15) | 0.0070 (12) | −0.0053 (11) |
C8 | 0.0792 (19) | 0.0393 (12) | 0.083 (2) | −0.0076 (12) | 0.0330 (16) | −0.0003 (13) |
C9 | 0.0376 (10) | 0.0418 (10) | 0.0354 (11) | −0.0096 (8) | 0.0174 (9) | −0.0041 (8) |
C10 | 0.0674 (16) | 0.0363 (11) | 0.0756 (18) | −0.0092 (10) | 0.0408 (15) | −0.0015 (11) |
C11 | 0.0414 (12) | 0.0763 (17) | 0.0444 (13) | −0.0210 (12) | 0.0128 (10) | −0.0058 (11) |
C12 | 0.0524 (13) | 0.0648 (15) | 0.0505 (13) | −0.0164 (11) | 0.0340 (12) | −0.0060 (11) |
C13 | 0.0446 (11) | 0.0330 (9) | 0.0306 (10) | 0.0099 (8) | 0.0154 (9) | 0.0040 (7) |
C14 | 0.0683 (16) | 0.0361 (11) | 0.0617 (15) | −0.0015 (10) | 0.0321 (13) | 0.0009 (10) |
C15 | 0.0770 (17) | 0.0474 (12) | 0.0304 (11) | 0.0249 (12) | 0.0138 (11) | 0.0092 (9) |
C16 | 0.0494 (13) | 0.0493 (12) | 0.0509 (13) | 0.0179 (10) | 0.0241 (11) | 0.0058 (10) |
P1—O1 | 1.6194 (16) | C6—H6B | 0.96 |
P1—O2 | 1.4791 (12) | C6—H6C | 0.96 |
P1—N1 | 1.6341 (14) | C7—H7A | 0.96 |
P1—N2 | 1.609 (2) | C7—H7B | 0.96 |
P2—O1 | 1.6191 (17) | C7—H7C | 0.96 |
P2—O3 | 1.4806 (12) | C8—H8A | 0.96 |
P2—N3 | 1.6351 (13) | C8—H8B | 0.96 |
P2—N4 | 1.6075 (18) | C8—H8C | 0.96 |
N1—C1 | 1.490 (3) | C9—C10 | 1.524 (3) |
N1—H1N | 0.87 (3) | C9—C11 | 1.523 (3) |
N2—C5 | 1.484 (2) | C9—C12 | 1.520 (4) |
N2—H2N | 0.868 (10) | C10—H10A | 0.96 |
N3—C9 | 1.485 (3) | C10—H10B | 0.96 |
N3—H3N | 0.87 (3) | C10—H10C | 0.96 |
N4—C13 | 1.485 (2) | C11—H11A | 0.96 |
N4—H4N | 0.866 (12) | C11—H11B | 0.96 |
C1—C2 | 1.533 (4) | C11—H11C | 0.96 |
C1—C3 | 1.525 (3) | C12—H12A | 0.96 |
C1—C4 | 1.518 (4) | C12—H12B | 0.96 |
C2—H2A | 0.96 | C12—H12C | 0.96 |
C2—H2B | 0.96 | C13—C14 | 1.526 (3) |
C2—H2C | 0.96 | C13—C15 | 1.517 (3) |
C3—H3A | 0.96 | C13—C16 | 1.526 (4) |
C3—H3B | 0.96 | C14—H14A | 0.96 |
C3—H3C | 0.96 | C14—H14B | 0.96 |
C4—H4A | 0.96 | C14—H14C | 0.96 |
C4—H4B | 0.96 | C15—H15A | 0.96 |
C4—H4C | 0.96 | C15—H15B | 0.96 |
C5—C6 | 1.514 (5) | C15—H15C | 0.96 |
C5—C7 | 1.509 (3) | C16—H16A | 0.96 |
C5—C8 | 1.518 (3) | C16—H16B | 0.96 |
C6—H6A | 0.96 | C16—H16C | 0.96 |
P1—O1—P2 | 126.85 (8) | C5—C7—H7A | 109.4718 |
O1—P1—O2 | 111.38 (8) | C5—C7—H7B | 109.4709 |
O1—P1—N1 | 100.28 (8) | C5—C7—H7C | 109.471 |
O1—P1—N2 | 106.84 (8) | H7A—C7—H7B | 109.4712 |
O2—P1—N1 | 116.84 (7) | H7A—C7—H7C | 109.4708 |
O2—P1—N2 | 109.89 (8) | H7B—C7—H7C | 109.4715 |
N1—P1—N2 | 110.86 (9) | C5—C8—H8A | 109.4718 |
O1—P2—O3 | 110.79 (8) | C5—C8—H8B | 109.4714 |
O1—P2—N3 | 99.81 (8) | C5—C8—H8C | 109.4699 |
O1—P2—N4 | 107.09 (9) | H8A—C8—H8B | 109.4718 |
O3—P2—N3 | 117.26 (7) | H8A—C8—H8C | 109.4709 |
O3—P2—N4 | 110.13 (8) | H8B—C8—H8C | 109.4716 |
N3—P2—N4 | 110.93 (8) | N3—C9—C10 | 109.0 (2) |
P1—N1—C1 | 124.93 (13) | N3—C9—C11 | 106.49 (18) |
P1—N1—H1N | 112.6 (14) | N3—C9—C12 | 110.78 (17) |
C1—N1—H1N | 109.9 (15) | C10—C9—C11 | 110.20 (18) |
P1—N2—C5 | 131.48 (15) | C10—C9—C12 | 110.3 (2) |
P1—N2—H2N | 115.1 (15) | C11—C9—C12 | 110.0 (2) |
C5—N2—H2N | 110.2 (15) | C9—C10—H10A | 109.4709 |
P2—N3—C9 | 124.49 (14) | C9—C10—H10B | 109.4713 |
P2—N3—H3N | 112.4 (14) | C9—C10—H10C | 109.4703 |
C9—N3—H3N | 109.1 (15) | H10A—C10—H10B | 109.4709 |
P2—N4—C13 | 133.65 (15) | H10A—C10—H10C | 109.4725 |
P2—N4—H4N | 114.7 (15) | H10B—C10—H10C | 109.4714 |
C13—N4—H4N | 111.2 (15) | C9—C11—H11A | 109.4714 |
N1—C1—C2 | 110.36 (17) | C9—C11—H11B | 109.4711 |
N1—C1—C3 | 107.17 (17) | C9—C11—H11C | 109.4709 |
N1—C1—C4 | 109.5 (2) | H11A—C11—H11B | 109.472 |
C2—C1—C3 | 109.2 (2) | H11A—C11—H11C | 109.4712 |
C2—C1—C4 | 109.9 (2) | H11B—C11—H11C | 109.4707 |
C3—C1—C4 | 110.71 (19) | C9—C12—H12A | 109.4707 |
C1—C2—H2A | 109.4703 | C9—C12—H12B | 109.471 |
C1—C2—H2B | 109.4716 | C9—C12—H12C | 109.4721 |
C1—C2—H2C | 109.472 | H12A—C12—H12B | 109.4706 |
H2A—C2—H2B | 109.4709 | H12A—C12—H12C | 109.4716 |
H2A—C2—H2C | 109.4714 | H12B—C12—H12C | 109.4712 |
H2B—C2—H2C | 109.4712 | N4—C13—C14 | 107.98 (16) |
C1—C3—H3A | 109.4714 | N4—C13—C15 | 111.94 (17) |
C1—C3—H3B | 109.4712 | N4—C13—C16 | 107.05 (19) |
C1—C3—H3C | 109.4713 | C14—C13—C15 | 110.1 (2) |
H3A—C3—H3B | 109.4718 | C14—C13—C16 | 109.5 (2) |
H3A—C3—H3C | 109.471 | C15—C13—C16 | 110.2 (2) |
H3B—C3—H3C | 109.4706 | C13—C14—H14A | 109.4718 |
C1—C4—H4A | 109.4713 | C13—C14—H14B | 109.4713 |
C1—C4—H4B | 109.4713 | C13—C14—H14C | 109.4706 |
C1—C4—H4C | 109.4717 | H14A—C14—H14B | 109.4713 |
H4A—C4—H4B | 109.4713 | H14A—C14—H14C | 109.4713 |
H4A—C4—H4C | 109.4706 | H14B—C14—H14C | 109.471 |
H4B—C4—H4C | 109.4712 | C13—C15—H15A | 109.4714 |
N2—C5—C6 | 106.5 (2) | C13—C15—H15B | 109.4713 |
N2—C5—C7 | 112.21 (19) | C13—C15—H15C | 109.4712 |
N2—C5—C8 | 108.33 (17) | H15A—C15—H15B | 109.4703 |
C6—C5—C7 | 109.9 (2) | H15A—C15—H15C | 109.4711 |
C6—C5—C8 | 109.9 (2) | H15B—C15—H15C | 109.4721 |
C7—C5—C8 | 109.9 (2) | C13—C16—H16A | 109.4713 |
C5—C6—H6A | 109.4718 | C13—C16—H16B | 109.471 |
C5—C6—H6B | 109.4713 | C13—C16—H16C | 109.4709 |
C5—C6—H6C | 109.4716 | H16A—C16—H16B | 109.4709 |
H6A—C6—H6B | 109.4706 | H16A—C16—H16C | 109.4717 |
H6A—C6—H6C | 109.4711 | H16B—C16—H16C | 109.4715 |
H6B—C6—H6C | 109.4709 | ||
O2—P1—O1—P2 | 57.79 (11) | O1—P2—N4—C13 | 50.9 (2) |
N1—P1—O1—P2 | −66.53 (11) | O3—P2—N4—C13 | 171.4 (2) |
N2—P1—O1—P2 | 177.81 (10) | N3—P2—N4—C13 | −57.1 (2) |
O1—P1—N1—C1 | 163.63 (17) | P1—N1—C1—C2 | 36.9 (3) |
O2—P1—N1—C1 | 43.2 (2) | P1—N1—C1—C3 | 155.68 (16) |
N2—P1—N1—C1 | −83.77 (18) | P1—N1—C1—C4 | −84.2 (2) |
O1—P1—N2—C5 | 46.3 (2) | P1—N2—C5—C6 | 148.66 (19) |
O2—P1—N2—C5 | 167.22 (18) | P1—N2—C5—C7 | 28.4 (3) |
N1—P1—N2—C5 | −62.1 (2) | P1—N2—C5—C8 | −93.1 (2) |
O3—P2—O1—P1 | 59.76 (11) | P2—N3—C9—C10 | −82.0 (2) |
N3—P2—O1—P1 | −64.50 (11) | P2—N3—C9—C11 | 159.08 (16) |
N4—P2—O1—P1 | 179.88 (10) | P2—N3—C9—C12 | 39.5 (3) |
O1—P2—N3—C9 | 162.53 (16) | P2—N4—C13—C14 | −102.9 (2) |
O3—P2—N3—C9 | 42.9 (2) | P2—N4—C13—C15 | 18.6 (3) |
N4—P2—N3—C9 | −84.80 (18) | P2—N4—C13—C16 | 139.33 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.87 (3) | 2.29 (3) | 3.046 (3) | 145 (2) |
N2—H2N···O3i | 0.87 (1) | 1.99 (1) | 2.8531 (19) | 177 (2) |
N3—H3N···O2 | 0.87 (3) | 2.24 (3) | 3.007 (3) | 147 (2) |
N4—H4N···O2ii | 0.87 (1) | 2.02 (1) | 2.883 (2) | 175 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C10H26N3OP | C16H40N4O3P2 |
Mr | 235.31 | 398.5 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21/c |
Temperature (K) | 150 | 150 |
a, b, c (Å) | 12.0615 (4), 21.2567 (7), 17.1877 (6) | 11.3715 (4), 17.7755 (7), 13.6956 (5) |
β (°) | 90.529 (3) | 119.371 (4) |
V (Å3) | 4406.5 (3) | 2412.51 (18) |
Z | 12 | 4 |
Radiation type | Mo Kα | Cu Kα |
µ (mm−1) | 0.17 | 1.80 |
Crystal size (mm) | 0.40 × 0.25 × 0.22 | 0.37 × 0.22 × 0.09 |
Data collection | ||
Diffractometer | Agilent Gemini-S with Sapphire3 detector diffractometer | Gemini Ultra diffractometer with Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) | Multi-scan (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.558, 1.000 | 0.746, 1.000 |
No. of measured, independent and observed reflections | 29385, 17386, 11821 [I > 2σ(I)] | 15622, 4265, 3420 [I > 3σ(I)] |
Rint | 0.051 | 0.033 |
(sin θ/λ)max (Å−1) | 0.685 | 0.598 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.161, 0.92 | 0.040, 0.107, 1.60 |
No. of reflections | 17382 | 4265 |
No. of parameters | 947 | 238 |
No. of restraints | 207 | 4 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.53, −0.57 | 0.33, −0.21 |
Absolute structure | Flack (1983), with how many Friedel pairs? | ? |
Absolute structure parameter | 0.00 (8) | ? |
Computer programs: CrysAlis PRO (Agilent, 2010), SUPERFLIP (Palatinus & Chapuis, 2007), Mercury (Macrae et al., 2008), CRYSTALS (Betteridge et al., 2003) and enCIFer (Allen et al., 2004), JANA2006 (Petříček et al., 2006) and enCIFer (Allen et al., 2004).
P1—O2 | 1.481 (3) | P46—O47 | 1.474 (3) |
P1—N3 | 1.646 (4) | P46—N48 | 1.631 (4) |
P1—N6 | 1.639 (3) | P46—N53 | 1.651 (4) |
P1—N11 | 1.629 (3) | P46—N56 | 1.645 (3) |
P16—O17 | 1.472 (3) | P61—O62 | 1.484 (3) |
P16—N18 | 1.635 (4) | P61—N63 | 1.644 (4) |
P16—N21 | 1.641 (3) | P61—N68 | 1.624 (3) |
P16—N26 | 1.645 (3) | P61—N73 | 1.650 (4) |
P31—O32 | 1.481 (3) | P76—O77 | 1.484 (3) |
P31—N33 | 1.636 (3) | P76—N78 | 1.652 (4) |
P31—N38 | 1.642 (3) | P76—N81 | 1.612 (3) |
P31—N43 | 1.640 (4) | P76—N86 | 1.630 (4) |
O2—P1—N3 | 106.67 (17) | O47—P46—N48 | 117.44 (17) |
O2—P1—N6 | 115.95 (18) | O47—P46—N53 | 106.71 (17) |
N3—P1—N6 | 110.01 (19) | N48—P46—N53 | 106.44 (19) |
O2—P1—N11 | 117.89 (18) | O47—P46—N56 | 116.76 (18) |
N3—P1—N11 | 106.8 (2) | N48—P46—N56 | 99.03 (17) |
N6—P1—N11 | 99.08 (17) | N53—P46—N56 | 109.93 (19) |
O17—P16—N18 | 106.97 (18) | O62—P61—N63 | 117.21 (18) |
O17—P16—N21 | 117.46 (19) | O62—P61—N68 | 118.09 (18) |
N18—P16—N21 | 108.2 (2) | N63—P61—N68 | 99.12 (17) |
O17—P16—N26 | 116.42 (19) | O62—P61—N73 | 107.09 (19) |
N18—P16—N26 | 107.7 (2) | N63—P61—N73 | 107.6 (2) |
N21—P16—N26 | 99.50 (17) | N68—P61—N73 | 107.0 (2) |
O32—P31—N33 | 116.98 (17) | O77—P76—N78 | 106.81 (17) |
O32—P31—N38 | 117.15 (17) | O77—P76—N81 | 116.69 (18) |
N33—P31—N38 | 99.41 (17) | N78—P76—N81 | 107.4 (2) |
O32—P31—N43 | 105.90 (18) | O77—P76—N86 | 116.79 (18) |
N33—P31—N43 | 108.7 (2) | N78—P76—N86 | 108.8 (2) |
N38—P31—N43 | 108.34 (19) | N81—P76—N86 | 99.87 (16) |
O77—P76—N78—C79 | 0.2 (5) | O32—P31—N43—C45 | −175.5 (4) |
O77—P76—N78—C80 | −176.8 (4) | O32—P31—N43—C44 | 4.9 (4) |
O2—P1—N3—C4 | −7.1 (5) | O47—P46—N53—C54 | −9.5 (4) |
O2—P1—N3—C5 | −171.3 (5) | O47—P46—N53—C55 | −168.1 (3) |
O17—P16—N18—C20 | 4.2 (6) | O62—P61—N73—C74 | −177.7 (4) |
O17—P16—N18—C19 | −176.8 (4) | O62—P61—N73—C75 | 3.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H61···O77 | 0.86 | 2.10 | 2.937 (9) | 165 |
N11—H111···O77 | 0.85 | 2.08 | 2.911 (9) | 164 |
N21—H211···O62 | 0.85 | 2.21 | 3.038 (9) | 162 |
N26—H261···O62 | 0.86 | 2.11 | 2.952 (9) | 166 |
N33—H331···O17 | 0.85 | 2.10 | 2.943 (9) | 167 |
N38—H381···O17 | 0.87 | 2.22 | 3.046 (9) | 159 |
N48—H481···O2 | 0.86 | 2.16 | 2.981 (9) | 161 |
N56—H561···O2 | 0.87 | 2.10 | 2.931 (9) | 158 |
N63—H631···O32i | 0.86 | 2.17 | 2.994 (9) | 160 |
N68—H681···O32i | 0.86 | 2.04 | 2.884 (9) | 168 |
N81—H811···O47i | 0.86 | 2.09 | 2.927 (9) | 166 |
N86—H861···O47i | 0.85 | 2.16 | 2.986 (9) | 163 |
Symmetry code: (i) x+1, y, z. |
P1—O1 | 1.6194 (16) | P2—O1 | 1.6191 (17) |
P1—O2 | 1.4791 (12) | P2—O3 | 1.4806 (12) |
P1—N1 | 1.6341 (14) | P2—N3 | 1.6351 (13) |
P1—N2 | 1.609 (2) | P2—N4 | 1.6075 (18) |
P1—O1—P2 | 126.85 (8) | O1—P2—O3 | 110.79 (8) |
O1—P1—O2 | 111.38 (8) | O1—P2—N3 | 99.81 (8) |
O1—P1—N1 | 100.28 (8) | O1—P2—N4 | 107.09 (9) |
O1—P1—N2 | 106.84 (8) | O3—P2—N3 | 117.26 (7) |
O2—P1—N1 | 116.84 (7) | O3—P2—N4 | 110.13 (8) |
O2—P1—N2 | 109.89 (8) | N3—P2—N4 | 110.93 (8) |
N1—P1—N2 | 110.86 (9) | ||
O2—P1—O1—P2 | 57.79 (11) | O3—P2—O1—P1 | 59.76 (11) |
N1—P1—O1—P2 | −66.53 (11) | N3—P2—O1—P1 | −64.50 (11) |
N2—P1—O1—P2 | 177.81 (10) | N4—P2—O1—P1 | 179.88 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.87 (3) | 2.29 (3) | 3.046 (3) | 145.2 (16) |
N2—H2N···O3i | 0.868 (10) | 1.986 (11) | 2.8531 (19) | 177 (2) |
N3—H3N···O2 | 0.87 (3) | 2.24 (3) | 3.007 (3) | 147.1 (16) |
N4—H4N···O2ii | 0.866 (12) | 2.019 (13) | 2.883 (2) | 175 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
The strengths of PO···H—N hydrogen bonds were investigated recently in compounds having C(O)NHP(O)[NH]2 and C(O)NHP(O)[N]2 skeletons (Pourayoubi, Tarahhomi et al., 2011). In another recent report by our group, the double hydrogen-bond acceptor capability of the P(O) unit in phosphoramidates, and the formation of the PO···[H—N][H—N] grouping, were discussed (Pourayoubi et al., 2012).
We report here a study of the hydrogen-bond patterns in new compounds having (N)P(O)(NH)2 and (NH)2P(O)(O)P(O)(NH)2 fragments [with n H-atom acceptors and 2n H-atom donor centres, with n = 1 and 2], with a double hydrogen-bond acceptor capability at the P(O) group. The observed hydrogen-bond patterns are compared with those of analogous structures. Moreover, the strengths of the PO···[H—N]x (x = 1, 2 or 3) hydrogen bonds are analysed for the new structures, for previously reported analogous compounds and also for compounds with (N)2P(O)(NH) and P(O)(NH)3 skeletons, for comparison.
A search of the Cambridge Structural Database (CSD, Version 5.32, May 2011 update; Allen, 2002; CSD refcodes will be given in capitals followed by the primary reference) shows that the N atom of the P(O)N group in phosphoramidate compounds does not usually act as a hydrogen-bond acceptor because of its weak Lewis base character; only one N—H···N—P hydrogen bond has been observed so far, in 4-I-C6H4NHP(O)[NHCH2CH2CH2NH] (HESCEO; Marsh, 1995).
In compounds having an (N)P(O)(NH)2 skeleton (six structures), three different linear arrangements were observed: (i) formed through PO···H—N hydrogen bonds, with one N—H unit not involved in hydrogen bonding (Fig. 1a) (NUVROL; Bourne et al., 1998); (ii) with molecules linked by an R21(6) ring (Fig. 1b) (MIFYIJ; Gholivand et al., 2002); and (iii) formed via an R22(8) ring (Fig. 1c) (IKASAP; Sabbaghi et al., 2011) [see Bernstein et al. (1995) for nomenclature of hydrogen-bond motifs]. In the two latter cases, with PO···(H—N)(H—N) groups, the phosphoryl O atom acts as a double hydrogen-bond acceptor.
In a compound with an (N)P(O)(NH)2 skeleton, but with one additional hydrogen-bond acceptor present (nitrogen) in the substituent (pyridine) linked to the amido N atom (HIVLII; Gholivand et al., 2008), the PO···H—N hydrogen bond also mediates a linear arrangement, although an intramolecular N—H···N hydrogen bond is also found in the structure.
The molecular structure of (I), with an (N)P(O)(NH)2 skeleton, is shown in Fig. 2. The asymmetric unit of (I) is composed of six independent molecules. The P atom exhibits a distorted tetrahedral environment which is reflected in its bond lengths and angles (Table 1), as has been noted for other phosphoramide derivatives (Pourayoubi, Tarahhomi et al., 2011). The P═O and P—N bond lengths are comparable with those in similar compounds (IKASAP; Sabbaghi et al., 2011). In the (CH3)2NP(O) unit, the O—P—N—C torsion angles, which reflect the orientations of the methyl groups with respect to the phosphoryl group, are in the ranges -177.7 (4) to -168.1 (3)° and -9.5 (4) to 4.9 (4)°. Two independent one-dimensional chains are present in the extended structure, each chain containing three independent molecules. In each chain, adjacent molecules are linked via PO···[H—N]2 groups (Table 2), building R21(6) rings in a linear arrangement parallel to [100] (Fig. 3). In each of the independent molecules, the phosphoryl O atom acts as a double hydrogen-bond acceptor.
The hydrogen-bond pattern of a previously published structure, [CH3NH]P(O)[(CH3)NC(O)C(O)N(CH3)] (DIYMED; Hutton et al., 1986), is very similar to that of (I). The asymmetric unit contains four independent molecules which form two one-dimensional chains, each composed of two independent molecules.
Among the six independent molecules in the asymmetric unit of (I), five tert-butyl groups (of a total of 12) were found to be disordered. The relative site occupancies were refined to values in the range 0.1663–0.8337. Disorder in the tert-butyl groups was observed in some similar structures reported previously, even at low temperature (Chivers et al., 2003; Gholivand, Pourayoubi et al., 2005; Gholivand et al., 2009).
There are two previous examples of compounds having an (N)2P(O)(NH2) skeleton [BIXFOE (Kattuboina & Li, 2008) and GOMDOB (Hempel et al., 1999)], with hydrogen bonding mediating the formation of a one-dimensional chain for BIXFOE and a one-dimensional ladder with alternating R22(8) and R42(8) rings for GOMDOB. In the latter, the phosphoryl O atom acts as a double hydrogen-bond acceptor (Fig. 4).
The molecular structure of (II) is shown in Fig. 5. As in (I), the P atoms exhibit a distorted tetrahedral environment, with bond angles at P1 in the range 100.28 (8)–116.84 (7)°. The P═O and P—N bond lengths are as expected in (II) (Table 3). The two [(CH3)3CNH]2P(O) units are bridged via an O atom [P—O—P = 126.85 (8)°]. The P1—O1 and P2—O1 bond lengths [1.619 (2) Å for both] are standard for the P—O—P moiety (Pourayoubi et al., 2010). The bridging O atom of the P—O—P fragment does not take part in hydrogen bonding. The hydrogen-bond motifs of this compound, which contains an (NH)2P(═O)OP(═O)(NH)2 skeleton, are similar to those found for compounds with an (N)P(═O)(NH)2 core. Only one neutral molecular structure with this skeleton has been reported so far: [P(O)(NHC6H4(2-CH3))2]2O [OXPOTU (Cameron et al., 1978) and OXPOTU01 (Pourayoubi, Padělková et al., 2011)]. In the structure of (II), each of the phosphoryl O atoms acts as a double hydrogen-bond acceptor, but in this case it participates in one intra- and one intermolecular N—H···O hydrogen bond (Table 4), building S(6) and R22(8) rings which are further linked into an extended chain parallel to the c axis (Fig. 6). This hydrogen-bond pattern has also been observed in [P(O)(NHC6H4(2-CH3))2]2O (OXPOTU and OXPOTU01). Compounds containing an (NH)2P(═O)OP(═O)(NH)2 group, when crystallized as salts, show a diversity of hydrogen-bond patterns, as in the case of the hydrated salt C48H100N14O3P62+.2Cl-.0.5HCl.3.5H2O (GAHGAZ; Ledger et al., 2010), which has a complicated hydrogen-bond pattern, because H2O and Cl- are also involved.
In order to gauge the strengths of hydrogen bonds in this family of compounds, we have examined 58 previously reported neutral molecular structures (a few with unavailable CIFs were excluded) with the skeletons discussed in this work, and also compounds containing (N)2P(O)(NH) and P(O)(NH)3 skeletons for comparision. A scatter plot of donor···acceptor (D···A) distances versus D—H···A angles for 104 N—H···O and N—H···N hydrogen bonds in these compounds is shown in Fig. 7. Contacts with D—H···A angles smaller than 110° and D···A distances greater than 3.3 Å were not included in Fig. 7. Cocrystals and solvates were also excluded.
Double hydrogen-bond acceptor capability is also found in the structures of compounds having a P(O)(NH)3 skeleton [for example, in P(O)[NHC6H4(4-OCH3)]3 (WAWNIS; Li et al., 2005) and P(O)[NHCH2C6H5]3 (TOKXIB; Gholivand et al., 2006)]. A four-centred P(O)···[H—N]3 skeleton [for example, in P(O)[NHCH3]3 (KABVAL; Chivers et al., 2003)] has also been reported.
The data reveal weak hydrogen bonding for P(O)[NHCH3]3 [KABVAL (Chivers et al., 2003); N···O and N—H···O are 2.970 (2) Å/172 (2)°, 2.961 (2) Å/155 (2)° and 3.253 (2) Å/171 (3)°]. For P(O)[NHC(CH3)3]3 (KABVEP; Chivers et al., 2003), three weak N—H···O hydrogen bonds, in a P(O)···[H—N]3 grouping, were found: 3.255 (4) Å/111.1 (2)°, 3.159 (4) Å/123.0 (2)° and 3.294 (4) Å/93.4 (2)°; the last of these, with a low N—H···O angle and marginal character, is not included in Fig. 7.
All data to the right of the dashed vertical line in Fig. 7 (D···A > 3.1 Å) are from N—H···N and PO···[H—N]x (x = 2 or 3) assemblies. However, this type of hydrogen-bond grouping is also found on the left side of the line.
The maximum population of the distribution is found for hydrogen bonds in the region with D···A = 2.80–3.05 Å and D—H···A = 144–179°.
The shortest N···O distances are found in two hydrogen bonds of [(CH3)2N]P(O)Y, where Y = NHCH(C6H5)CH(C6H5)N(C10H7) (both D···A = 2.75 Å), with different angles (XAVXEY; Alcock et al., 2005). Also, a short distance with a relatively linear angle (2.77 Å and 170°) occurs in the N—H···OP hydrogen bond of P(O)[HNC6H4(4-NO2)][NC5H9(4-CH3)]2 (WALQUW; Gholivand, Shariatinia & Pourayoubi, 2005).
Interestingly, a long donor–acceptor distance [3.477 (2) Å] is observed with a nearly linear angle [171 (2)°] for the N—H···O—(CH3) hydrogen bond in P(O)[NHC6H4(4-OCH3)]3 (WAWNIS; Li et al., 2005), which is not included in Fig. 7.