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The new compound N-(3-nitrobenzoyl)-N′,N′′-bis(tert-butyl)phosphoric triamide was synthesized by reacting 3-nitrobenzoyl phosphoramidic dichloride and tert-butyl amine, and characterized by multinuclear (1H, 13C and 31P) NMR and FTIR spectroscopy techniques. Structural and conformational properties were analyzed using single-crystal X-ray diffraction, vibrational spectra and theoretical calculations. The crystal structure contains three symmetry-independent disordered molecules, connected via intermolecular N—H...O=P and N—H...O=C hydrogen bonds to form a centrosymmetric hexameric chain extended along the [2,1,\bar 1] direction. The disorder is mainly caused by rotation of the tert-butyl groups around the C—N bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109020023/bp5021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109020023/bp5021Isup2.hkl
Contains datablock I

CCDC reference: 684213

Computing details top

Data collection: CrysAlis CCD (Oxford diffraction, 2007); cell refinement: CrysAlis RED (Oxford diffraction, 2007); data reduction: CrysAlis RED (Oxford diffraction, 2007); program(s) used to solve structure: Superflip(Palatinus L., Chapuis G., 2007); program(s) used to refine structure: Jana2006 (Petricek, Dusek & Palatinus, 2006); molecular graphics: Diamond (Brandenburg & Putz, 2005); software used to prepare material for publication: Jana2006 (Petricek, Dusek & Palatinus, 2006).

(I) top
Crystal data top
C90H150N24O24P6Z = 1
Mr = 2138.16F(000) = 1140
Triclinic, P1Dx = 1.263 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.1528 (2) ÅCell parameters from 14590 reflections
b = 13.7179 (2) Åθ = 2.6–39.3°
c = 16.5876 (2) ŵ = 0.17 mm1
α = 87.8019 (12)°T = 120 K
β = 70.8182 (13)°Irregular shape, pale yellow
γ = 83.8446 (14)°0.67 × 0.26 × 0.22 mm
V = 2810.41 (7) Å3
Data collection top
Oxford Diffraction CCD
diffractometer
11679 independent reflections
Radiation source: X-ray tube7286 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 8.3438 pixels mm-1θmax = 26.5°, θmin = 2.8°
Rotation method data acquisition using ω scansh = 1616
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.16 (release 23-01-2008 CrysAlis171 .NET) (compiled Jan 23 2008,18:08:03) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1717
Tmin = 0.945, Tmax = 0.963l = 2020
34749 measured reflections
Refinement top
Refinement on F300 constraints
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.044Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2)
S = 1.79(Δ/σ)max = 0.046
11679 reflectionsΔρmax = 0.37 e Å3
679 parametersΔρmin = 0.35 e Å3
0 restraints
Special details top

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 then the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.88086 (4)0.40917 (4)0.10429 (3)0.02764 (18)
P20.50902 (4)0.14229 (4)0.18806 (3)0.02790 (19)
P30.20898 (4)0.11482 (4)0.42939 (3)0.02812 (19)
O10.64239 (12)0.29458 (12)0.31107 (11)0.0607 (8)
O110.05296 (10)0.00015 (10)0.39539 (8)0.0370 (5)
O40.97334 (10)0.46291 (10)0.10079 (8)0.0379 (5)
O100.10680 (13)0.18281 (12)0.23778 (10)0.0554 (7)
O80.41323 (10)0.08718 (9)0.20723 (8)0.0344 (5)
O90.01813 (12)0.23171 (12)0.10865 (10)0.0592 (7)
O50.27968 (13)0.52456 (12)0.47006 (11)0.0646 (8)
O70.66664 (10)0.24902 (9)0.23026 (8)0.0337 (5)
N10.63704 (14)0.29631 (13)0.23609 (13)0.0443 (8)
N110.18432 (11)0.04104 (11)0.51124 (9)0.0278 (6)
N50.26939 (16)0.56268 (15)0.53776 (14)0.0557 (9)
O120.31085 (11)0.15909 (11)0.41082 (8)0.0484 (6)
O30.73101 (10)0.32642 (9)0.03265 (8)0.0342 (5)
O60.19059 (16)0.55881 (17)0.60175 (12)0.1027 (11)
N90.02620 (15)0.18767 (12)0.17387 (12)0.0413 (8)
O20.56822 (13)0.25917 (13)0.17757 (11)0.0630 (8)
N80.51104 (12)0.23592 (11)0.12389 (9)0.0327 (6)
N30.89290 (12)0.29342 (11)0.12757 (11)0.0414 (7)
N70.62500 (12)0.07758 (11)0.14506 (10)0.0326 (6)
N60.50668 (12)0.18549 (11)0.28423 (9)0.0285 (6)
N40.76491 (11)0.45248 (10)0.17169 (9)0.0271 (6)
N100.21783 (11)0.05329 (11)0.33994 (9)0.0278 (6)
N20.87127 (11)0.41812 (10)0.00427 (9)0.0278 (6)
C200.64141 (16)0.38284 (14)0.45655 (13)0.0353 (8)
C180.46852 (16)0.32945 (16)0.52213 (13)0.0441 (9)
N120.10135 (15)0.19181 (12)0.44507 (11)0.0473 (8)
C39a0.0732 (2)0.2911 (2)0.4804 (3)0.0328 (11)0.709 (14)
C39b0.0810 (6)0.2788 (6)0.5014 (5)0.0328 (11)0.291 (14)
C30.86794 (16)0.44105 (15)0.25575 (13)0.0425 (9)
C380.25833 (15)0.03726 (14)0.53150 (12)0.0359 (8)
C160.56882 (14)0.28674 (13)0.37565 (11)0.0276 (7)
C310.14952 (14)0.04617 (13)0.25189 (11)0.0276 (7)
C80.98429 (15)0.23395 (13)0.14361 (11)0.0339 (8)
C9a0.7228 (4)0.5575 (3)0.1958 (5)0.0293 (11)0.530 (17)
C9b0.7163 (5)0.5564 (4)0.1746 (5)0.0293 (11)0.470 (17)
C170.47647 (15)0.28345 (14)0.44706 (12)0.0362 (8)
C340.15470 (17)0.13395 (14)0.10106 (13)0.0378 (9)
C240.42503 (14)0.31796 (14)0.13302 (12)0.0327 (8)
C190.55164 (16)0.37941 (15)0.52804 (13)0.0389 (8)
C40.79066 (16)0.39602 (15)0.27713 (13)0.0398 (8)
C50.71873 (15)0.34629 (13)0.21364 (13)0.0323 (8)
C10.79765 (14)0.38574 (13)0.10969 (11)0.0271 (7)
C230.64395 (15)0.03201 (13)0.14509 (12)0.0383 (8)
C20.87213 (15)0.43590 (14)0.17329 (12)0.0344 (8)
C60.72022 (14)0.34082 (13)0.13113 (12)0.0296 (7)
C360.06258 (15)0.09452 (13)0.24985 (12)0.0278 (7)
C330.24160 (18)0.08738 (14)0.10364 (13)0.0419 (9)
C210.65208 (15)0.33799 (13)0.38127 (12)0.0332 (8)
C70.79748 (14)0.37470 (13)0.01909 (11)0.0279 (7)
C350.06708 (16)0.13687 (13)0.17467 (12)0.0313 (8)
C370.13701 (14)0.00310 (13)0.33431 (11)0.0275 (7)
C220.58387 (15)0.23881 (13)0.29190 (11)0.0281 (7)
C320.23946 (16)0.04328 (14)0.17842 (12)0.0339 (8)
H1c30.9191470.4762180.2986760.051*
H1c40.7874810.3994220.3341730.0478*
H1c60.6680770.3061570.0885190.0355*
H1c20.9265020.4669460.1597330.0413*
H1c170.4179180.2490440.4442220.0435*
H1c180.4043390.3265850.5707330.053*
H1c190.5468620.4105740.5801810.0466*
H1c210.7163520.3418910.3329190.0398*
H1c330.3039850.0854110.053430.0503*
H1c320.3001060.0107420.1794410.0407*
H1c340.1552650.1635160.0493740.0454*
H1c360.0004940.0982620.3000430.0333*
H1n70.6806620.1095930.1199330.0392*
H1n100.2764750.0540150.2960680.0333*
H1n20.9160330.4523070.0337470.0334*
H1n30.8374620.2621180.1310540.0496*
H1n40.7214820.4089410.1971830.0325*
H1n60.4538860.1726950.3298880.0342*
H1n80.5689220.2378490.0795020.0393*
H1n110.1191420.0487490.5477310.0333*
H1n120.0509740.1698860.4295220.0568*
C13a0.9597 (2)0.12773 (19)0.14475 (19)0.0571 (11)
C15a1.0891 (2)0.2489 (2)0.07210 (17)0.0537 (10)
C14a0.9930 (2)0.2605 (2)0.22893 (17)0.0645 (12)
H1c13a1.0171640.0852010.1548910.0685*
H2c13a0.8928920.1190460.1893290.0685*
H3c13a0.953510.1120390.0907520.0685*
H1c14a1.0487920.2172920.2407440.0774*
H2c14a1.0104030.3269610.2269140.0774*
H3c14a0.9251950.254150.2730920.0774*
H1c15a1.1459490.2021050.0780090.0644*
H2c15a1.079590.240040.0179910.0644*
H3c15a1.1078550.3140840.0752110.0644*
C11a0.6031 (2)0.5591 (7)0.2446 (4)0.0478 (13)0.571 (3)
C10a0.7786 (5)0.5987 (3)0.2520 (6)0.0542 (16)0.571 (3)
C12a0.7402 (5)0.6177 (4)0.1139 (5)0.0519 (16)0.571 (3)
H1c11a0.5924720.5147510.2921760.0574*0.571 (3)
H2c11a0.5746490.6242780.2649990.0574*0.571 (3)
H3c11a0.5662610.5393550.2075980.0574*0.571 (3)
H1c12a0.8162690.6169550.083760.0623*0.571 (3)
H2c12a0.705710.5900370.0786020.0623*0.571 (3)
H3c12a0.7094260.68410.1279270.0623*0.571 (3)
H1c10a0.7667030.5602190.3032530.065*0.571 (3)
H2c10a0.8547860.5965340.2218580.065*0.571 (3)
H3c10a0.7494420.665350.2664420.065*0.571 (3)
C11b0.6209 (4)0.5629 (7)0.2563 (4)0.0478 (14)0.429 (3)
C10b0.7989 (6)0.6219 (4)0.1817 (4)0.0542 (18)0.429 (3)
C12b0.6787 (6)0.5875 (4)0.0988 (4)0.0519 (18)0.429 (3)
H1c11b0.6435960.5356570.3025360.0574*0.429 (3)
H2c11b0.5931770.6303260.2681960.0574*0.429 (3)
H3c11b0.5652330.5268420.2500960.0574*0.429 (3)
H1c12b0.7398550.5838880.0472980.0623*0.429 (3)
H2c12b0.6276980.5446050.0943780.0623*0.429 (3)
H3c12b0.6448930.6536040.1069290.0623*0.429 (3)
H1c10b0.8215410.6015610.2297230.065*0.429 (3)
H2c10b0.8603850.6169790.130520.065*0.429 (3)
H3c10b0.7669390.6886170.1894770.065*0.429 (3)
C29a0.5900 (2)0.07471 (19)0.08806 (17)0.0509 (10)
C28a0.7666 (2)0.0570 (2)0.10879 (18)0.0511 (10)
C30a0.6013 (2)0.0737 (2)0.23590 (17)0.0660 (11)
H1c30a0.6203790.1433220.2347280.0792*
H2c30a0.6329250.0437470.2720890.0792*
H3c30a0.5240460.0601790.2576550.0792*
H1c29a0.6051680.1447720.0864420.0611*
H2c29a0.5131970.0577320.1103730.0611*
H3c29a0.6175080.0485750.0313940.0611*
H1c28a0.7831870.1268880.1065460.0614*
H2c28a0.7930570.0301030.0523080.0614*
H3c28a0.8003560.0295830.1447370.0614*
C26a0.4717 (4)0.4036 (4)0.0734 (4)0.0578 (17)0.420 (2)
C25a0.3379 (5)0.2798 (4)0.1096 (4)0.064 (2)0.420 (2)
C27a0.3803 (6)0.3611 (5)0.2245 (3)0.0638 (19)0.420 (2)
H1c27a0.3351920.3164810.262150.0766*0.420 (2)
H2c27a0.4394110.3708410.2441830.0766*0.420 (2)
H3c27a0.3384650.4228180.2238570.0766*0.420 (2)
H1c26a0.4147940.4549220.0766620.0694*0.420 (2)
H2c26a0.526650.4285350.0908470.0694*0.420 (2)
H3c26a0.5025180.3804290.0157090.0694*0.420 (2)
H1c25a0.3137690.2239580.1445420.077*0.420 (2)
H2c25a0.2784630.3298930.1182370.077*0.420 (2)
H3c25a0.3646580.2607870.0506140.077*0.420 (2)
C26b0.4355 (6)0.3555 (5)0.0442 (4)0.0578 (18)0.580 (2)
C25b0.3114 (7)0.2849 (6)0.1760 (5)0.064 (2)0.580 (2)
C27b0.4448 (7)0.3955 (6)0.1858 (5)0.064 (2)0.580 (2)
H1c27b0.4208990.3795460.2454660.0766*0.580 (2)
H2c27b0.5210640.4018980.1668360.0766*0.580 (2)
H3c27b0.4066320.4563270.176550.0766*0.580 (2)
H1c26b0.3835790.4113740.0482680.0694*0.580 (2)
H2c26b0.5072660.3749420.0192960.0694*0.580 (2)
H3c26b0.4242140.3064290.0091720.0694*0.580 (2)
H1c25b0.3062840.2544540.2300650.077*0.580 (2)
H2c25b0.2605460.342370.184610.077*0.580 (2)
H3c25b0.2953240.2396780.1401410.077*0.580 (2)
C44a0.2131 (6)0.0621 (5)0.6246 (3)0.070 (2)0.519 (4)
C43a0.3701 (5)0.0051 (5)0.5130 (6)0.093 (3)0.519 (4)
C45a0.2627 (6)0.1245 (4)0.4773 (4)0.084 (3)0.519 (4)
H1c45a0.3117780.1766950.4874960.101*0.519 (4)
H2c45a0.1917970.1461760.4917780.101*0.519 (4)
H3c45a0.2871930.1061840.4180930.101*0.519 (4)
H1c44a0.2052720.0044860.6580090.0844*0.519 (4)
H2c44a0.1437250.0859930.6360350.0844*0.519 (4)
H3c44a0.2613950.1117320.6392030.0844*0.519 (4)
H1c43a0.4011350.0068350.4528620.1122*0.519 (4)
H2c43a0.3652360.0539110.543820.1122*0.519 (4)
H3c43a0.4148980.0557230.530380.1122*0.519 (4)
C44b0.1881 (7)0.0993 (8)0.6006 (6)0.070 (2)0.481 (4)
C43b0.3258 (7)0.0161 (8)0.5747 (8)0.093 (4)0.481 (4)
C45b0.3311 (7)0.0967 (8)0.4597 (7)0.084 (3)0.481 (4)
H1c45b0.3794560.1424460.4782440.101*0.481 (4)
H2c45b0.2875490.131780.4367480.101*0.481 (4)
H3c45b0.3722130.0544760.4165410.101*0.481 (4)
H1c44b0.1384970.0589540.6455260.0844*0.481 (4)
H2c44b0.1481990.1352130.574710.0844*0.481 (4)
H3c44b0.2322770.1444740.6238470.0844*0.481 (4)
H1c43b0.3744110.0535510.5318320.1122*0.481 (4)
H2c43b0.2789640.0591450.6187090.1122*0.481 (4)
H3c43b0.3666530.031450.5988560.1122*0.481 (4)
C40a0.1090 (4)0.2965 (3)0.5592 (4)0.0517 (15)0.756 (3)
C41a0.0481 (3)0.3178 (3)0.5052 (4)0.0695 (17)0.756 (3)
C42a0.1323 (4)0.3590 (3)0.4116 (4)0.0605 (16)0.756 (3)
H1c40a0.0938540.3624550.5803120.062*0.756 (3)
H2c40a0.0702310.25330.6026570.062*0.756 (3)
H3c40a0.1852070.2770510.543780.062*0.756 (3)
H1c42a0.117090.4250060.4326660.0725*0.756 (3)
H2c42a0.2086940.3400290.3953650.0725*0.756 (3)
H3c42a0.1087740.355210.3629230.0725*0.756 (3)
H1c41a0.0657670.3838180.5261460.0833*0.756 (3)
H2c41a0.0705180.3126010.4560660.0833*0.756 (3)
H3c41a0.0847580.2738010.5488790.0833*0.756 (3)
C40b0.1495 (4)0.2849 (3)0.5598 (3)0.0517 (18)0.244 (3)
C41b0.0310 (3)0.2526 (3)0.5538 (3)0.0695 (17)0.244 (3)
C42b0.0733 (4)0.3747 (3)0.4556 (3)0.0605 (17)0.244 (3)
H1c40b0.1169470.336110.6008410.062*0.244 (3)
H2c40b0.1532440.2234770.5889050.062*0.244 (3)
H3c40b0.2211240.2989060.5260880.062*0.244 (3)
H1c42b0.0405690.4259710.49660.0725*0.244 (3)
H2c42b0.1444250.3893780.421310.0725*0.244 (3)
H3c42b0.0298330.3700150.4195970.0725*0.244 (3)
H1c41b0.0659770.3029070.5952920.0833*0.244 (3)
H2c41b0.0729580.2470760.5168610.0833*0.244 (3)
H3c41b0.0248330.1912050.5824820.0833*0.244 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0212 (3)0.0252 (3)0.0338 (3)0.0081 (2)0.0045 (2)0.0091 (2)
P20.0264 (3)0.0274 (3)0.0264 (3)0.0057 (2)0.0029 (2)0.0010 (2)
P30.0312 (3)0.0283 (3)0.0247 (3)0.0109 (2)0.0067 (2)0.0019 (2)
O10.0618 (11)0.0792 (13)0.0508 (11)0.0141 (9)0.0289 (9)0.0041 (9)
O110.0263 (7)0.0505 (9)0.0317 (8)0.0134 (7)0.0021 (6)0.0086 (6)
O40.0284 (8)0.0458 (9)0.0429 (8)0.0197 (7)0.0137 (6)0.0222 (7)
O100.0568 (11)0.0629 (11)0.0538 (11)0.0246 (9)0.0213 (9)0.0081 (8)
O80.0286 (7)0.0398 (8)0.0314 (8)0.0118 (6)0.0021 (6)0.0054 (6)
O90.0624 (11)0.0637 (11)0.0646 (11)0.0088 (9)0.0392 (9)0.0345 (9)
O50.0749 (12)0.0683 (12)0.0643 (12)0.0240 (10)0.0343 (10)0.0149 (9)
O70.0288 (7)0.0394 (8)0.0291 (7)0.0140 (6)0.0014 (6)0.0025 (6)
N10.0404 (11)0.0449 (12)0.0520 (13)0.0046 (9)0.0213 (10)0.0030 (9)
N110.0191 (8)0.0351 (9)0.0243 (9)0.0043 (7)0.0003 (6)0.0026 (7)
N50.0576 (14)0.0610 (14)0.0562 (14)0.0258 (11)0.0220 (11)0.0063 (11)
O120.0507 (9)0.0651 (10)0.0280 (8)0.0400 (8)0.0001 (7)0.0026 (7)
O30.0332 (8)0.0334 (8)0.0314 (8)0.0169 (6)0.0004 (6)0.0026 (6)
O60.0784 (14)0.157 (2)0.0728 (14)0.0808 (15)0.0002 (11)0.0302 (13)
N90.0513 (12)0.0339 (10)0.0484 (12)0.0020 (9)0.0304 (10)0.0087 (9)
O20.0560 (11)0.0791 (13)0.0667 (12)0.0347 (10)0.0306 (9)0.0196 (10)
N80.0230 (9)0.0373 (10)0.0277 (9)0.0020 (8)0.0036 (7)0.0036 (7)
N30.0226 (9)0.0280 (10)0.0667 (12)0.0071 (8)0.0062 (8)0.0189 (9)
N70.0266 (9)0.0235 (9)0.0420 (10)0.0069 (7)0.0019 (7)0.0011 (7)
N60.0284 (9)0.0292 (9)0.0240 (9)0.0132 (7)0.0005 (7)0.0029 (7)
N40.0255 (9)0.0221 (9)0.0311 (9)0.0114 (7)0.0033 (7)0.0036 (7)
N100.0223 (9)0.0340 (9)0.0244 (9)0.0089 (7)0.0021 (7)0.0012 (7)
N20.0236 (9)0.0255 (9)0.0281 (9)0.0096 (7)0.0017 (7)0.0055 (7)
C200.0382 (12)0.0286 (11)0.0434 (13)0.0108 (10)0.0172 (10)0.0021 (9)
C180.0360 (13)0.0591 (15)0.0327 (13)0.0079 (11)0.0029 (10)0.0102 (11)
N120.0632 (13)0.0326 (10)0.0532 (12)0.0095 (9)0.0318 (10)0.0106 (9)
C39a0.0410 (14)0.0272 (15)0.029 (2)0.0005 (11)0.0108 (12)0.0005 (14)
C39b0.0410 (14)0.0272 (15)0.029 (2)0.0005 (11)0.0108 (12)0.0005 (14)
C30.0442 (13)0.0448 (14)0.0315 (13)0.0136 (11)0.0009 (10)0.0076 (10)
C380.0310 (12)0.0368 (12)0.0385 (12)0.0005 (10)0.0113 (9)0.0072 (9)
C160.0299 (11)0.0244 (10)0.0285 (11)0.0069 (9)0.0085 (8)0.0036 (8)
C310.0307 (11)0.0231 (10)0.0288 (11)0.0002 (9)0.0103 (8)0.0005 (8)
C80.0421 (13)0.0303 (11)0.0299 (11)0.0036 (10)0.0153 (9)0.0030 (9)
C9a0.0310 (13)0.0259 (12)0.030 (2)0.0041 (10)0.0086 (14)0.0009 (13)
C9b0.0310 (13)0.0259 (12)0.030 (2)0.0041 (10)0.0086 (14)0.0009 (13)
C170.0312 (12)0.0427 (13)0.0334 (12)0.0114 (10)0.0058 (9)0.0059 (10)
C340.0619 (15)0.0233 (11)0.0303 (12)0.0038 (10)0.0195 (11)0.0048 (9)
C240.0243 (11)0.0332 (12)0.0375 (12)0.0016 (9)0.0073 (9)0.0010 (9)
C190.0469 (13)0.0377 (12)0.0351 (13)0.0016 (11)0.0175 (10)0.0086 (10)
C40.0438 (13)0.0422 (13)0.0318 (12)0.0027 (11)0.0107 (10)0.0016 (10)
C50.0302 (11)0.0266 (11)0.0397 (13)0.0016 (9)0.0122 (9)0.0014 (9)
C10.0250 (10)0.0202 (10)0.0303 (11)0.0011 (8)0.0016 (8)0.0007 (8)
C230.0446 (13)0.0267 (11)0.0369 (12)0.0005 (10)0.0053 (10)0.0004 (9)
C20.0345 (12)0.0318 (12)0.0332 (12)0.0099 (9)0.0042 (9)0.0005 (9)
C60.0255 (11)0.0226 (10)0.0348 (12)0.0004 (9)0.0033 (9)0.0037 (8)
C360.0301 (11)0.0236 (10)0.0298 (11)0.0016 (9)0.0113 (9)0.0005 (8)
C330.0535 (15)0.0324 (12)0.0314 (12)0.0026 (11)0.0028 (10)0.0012 (9)
C210.0322 (12)0.0330 (12)0.0341 (12)0.0085 (10)0.0092 (9)0.0033 (9)
C70.0247 (10)0.0202 (10)0.0325 (11)0.0037 (8)0.0005 (8)0.0004 (8)
C350.0415 (12)0.0200 (10)0.0369 (12)0.0026 (9)0.0203 (10)0.0019 (8)
C370.0259 (11)0.0273 (11)0.0298 (11)0.0034 (9)0.0093 (9)0.0002 (8)
C220.0297 (11)0.0244 (10)0.0288 (11)0.0068 (9)0.0069 (9)0.0059 (8)
C320.0369 (12)0.0301 (11)0.0323 (12)0.0049 (9)0.0074 (9)0.0013 (9)
C13a0.0732 (18)0.0323 (13)0.0767 (19)0.0063 (12)0.0430 (15)0.0002 (12)
C15a0.0323 (13)0.0719 (18)0.0559 (15)0.0093 (12)0.0162 (11)0.0147 (13)
C14a0.105 (2)0.0589 (17)0.0387 (14)0.0304 (15)0.0305 (14)0.0104 (12)
C11a0.0423 (18)0.0426 (16)0.048 (2)0.0023 (16)0.0022 (16)0.008 (2)
C10a0.062 (3)0.038 (2)0.065 (3)0.0041 (18)0.023 (2)0.0215 (19)
C12a0.068 (3)0.0314 (19)0.047 (2)0.0073 (19)0.0100 (17)0.0069 (16)
C11b0.053 (2)0.041 (2)0.0413 (18)0.0040 (19)0.0059 (15)0.0081 (17)
C10b0.062 (3)0.027 (2)0.072 (2)0.010 (2)0.0175 (19)0.0073 (16)
C12b0.069 (4)0.040 (2)0.0484 (19)0.016 (2)0.028 (2)0.0004 (16)
C29a0.0527 (15)0.0348 (13)0.0572 (15)0.0141 (12)0.0031 (12)0.0090 (11)
C28a0.0515 (14)0.0342 (13)0.0620 (16)0.0080 (11)0.0141 (12)0.0053 (11)
C30a0.085 (2)0.0497 (16)0.0481 (15)0.0060 (15)0.0058 (13)0.0119 (12)
C26a0.0435 (19)0.046 (3)0.076 (3)0.0054 (17)0.013 (2)0.019 (2)
C25a0.043 (3)0.059 (2)0.106 (4)0.0002 (19)0.047 (3)0.000 (3)
C27a0.064 (3)0.055 (3)0.063 (2)0.0289 (19)0.017 (2)0.015 (2)
C26b0.059 (3)0.058 (2)0.048 (2)0.021 (2)0.0140 (19)0.0069 (17)
C25b0.025 (4)0.066 (3)0.089 (3)0.005 (2)0.007 (2)0.0130 (19)
C27b0.073 (4)0.036 (3)0.086 (2)0.018 (2)0.036 (2)0.0159 (18)
C44a0.093 (4)0.068 (5)0.0421 (19)0.027 (3)0.023 (2)0.010 (2)
C43a0.035 (2)0.082 (4)0.164 (7)0.001 (3)0.039 (4)0.033 (4)
C45a0.125 (6)0.045 (3)0.096 (4)0.046 (4)0.069 (4)0.026 (3)
C44b0.060 (3)0.069 (4)0.068 (4)0.007 (3)0.009 (2)0.038 (3)
C43b0.094 (3)0.073 (5)0.158 (8)0.002 (3)0.104 (4)0.003 (5)
C45b0.083 (4)0.087 (3)0.062 (7)0.059 (3)0.017 (4)0.001 (4)
C40a0.071 (3)0.045 (2)0.0412 (16)0.010 (2)0.020 (2)0.0064 (14)
C41a0.060 (2)0.052 (2)0.091 (3)0.0190 (18)0.021 (2)0.0291 (19)
C42a0.101 (3)0.0328 (19)0.045 (2)0.0119 (19)0.0184 (19)0.0074 (15)
C40b0.069 (3)0.048 (3)0.0437 (17)0.001 (2)0.0269 (19)0.0083 (15)
C41b0.052 (3)0.081 (3)0.058 (2)0.0003 (19)0.0061 (19)0.0287 (18)
C42b0.091 (3)0.038 (2)0.0539 (19)0.020 (2)0.0330 (18)0.0057 (15)
Geometric parameters (Å, º) top
P1—O41.4727 (15)C36—C351.377 (3)
P1—N31.6232 (16)C36—H1c360.96
P1—N41.6324 (13)C33—C321.392 (3)
P1—N21.7036 (17)C33—H1c330.96
P2—O81.4774 (14)C21—H1c210.96
P2—N81.6332 (16)C32—H1c320.96
P2—N71.6330 (14)C13a—H1c13a0.96
P2—N61.7127 (17)C13a—H2c13a0.96
P3—N111.6275 (15)C13a—H3c13a0.96
P3—O121.4656 (16)C15a—H1c15a0.96
P3—N101.6996 (16)C15a—H2c15a0.96
P3—N121.6265 (18)C15a—H3c15a0.96
O1—N11.224 (3)C14a—H1c14a0.96
O11—C371.2337 (19)C14a—H2c14a0.96
O10—N91.226 (2)C14a—H3c14a0.96
O9—N91.228 (3)C11a—H1c11a0.96
O5—N51.218 (3)C11a—H2c11a0.96
O7—C221.2411 (19)C11a—H3c11a0.96
N1—O21.227 (2)C10a—H1c10a0.96
N1—C51.485 (3)C10a—H2c10a0.96
N11—C381.476 (3)C10a—H3c10a0.96
N11—H1n110.87C12a—H1c12a0.96
N5—O61.220 (3)C12a—H2c12a0.96
N5—C20i1.487 (3)C12a—H3c12a0.96
O3—C71.236 (2)C11b—H1c11b0.96
N9—C351.478 (3)C11b—H2c11b0.96
N8—C241.482 (2)C11b—H3c11b0.96
N8—H1n80.87C10b—H1c10b0.96
N3—C81.471 (3)C10b—H2c10b0.96
N3—H1n30.87C10b—H3c10b0.96
N7—C231.497 (2)C12b—H1c12b0.96
N7—H1n70.87C12b—H2c12b0.96
N6—C221.354 (3)C12b—H3c12b0.96
N6—H1n60.87C29a—H1c29a0.96
N4—H1n40.87C29a—H2c29a0.96
N10—C371.356 (3)C29a—H3c29a0.96
N10—H1n100.87C28a—H1c28a0.96
N2—C71.355 (3)C28a—H2c28a0.96
N2—H1n20.87C28a—H3c28a0.96
C20—C191.375 (3)C30a—H1c30a0.96
C20—C211.372 (3)C30a—H2c30a0.96
C18—C171.386 (3)C30a—H3c30a0.96
C18—C191.382 (3)C26a—H1c26a0.96
C18—H1c180.96C26a—H2c26a0.96
N12—H1n120.87C26a—H3c26a0.96
C39a—C40a1.533 (8)C25a—H1c25a0.96
C39a—C41a1.518 (4)C25a—H2c25a0.96
C39a—C42a1.505 (6)C25a—H3c25a0.96
C39b—C40b1.533 (11)C27a—H1c27a0.96
C39b—C41b1.518 (8)C27a—H2c27a0.96
C39b—C42b1.505 (9)C27a—H3c27a0.96
C3—C41.389 (3)C26b—H1c26b0.96
C3—C21.386 (3)C26b—H2c26b0.96
C3—H1c30.96C26b—H3c26b0.96
C38—C44a1.501 (5)C25b—H1c25b0.96
C38—C43a1.510 (7)C25b—H2c25b0.96
C38—C45a1.510 (7)C25b—H3c25b0.96
C38—C44b1.514 (10)C27b—H1c27b0.96
C38—C43b1.559 (13)C27b—H2c27b0.96
C38—C45b1.468 (10)C27b—H3c27b0.96
C16—C171.394 (2)C44a—H1c44a0.96
C16—C211.393 (3)C44a—H2c44a0.96
C16—C221.504 (3)C44a—H3c44a0.96
C31—C361.392 (3)C43a—H1c43a0.96
C31—C371.501 (3)C43a—H2c43a0.96
C31—C321.395 (2)C43a—H3c43a0.96
C8—C13a1.524 (3)C45a—H1c45a0.96
C8—C15a1.522 (3)C45a—H2c45a0.96
C8—C14a1.518 (4)C45a—H3c45a0.96
C9a—C11a1.513 (6)C44b—H1c44b0.96
C9a—C10a1.518 (12)C44b—H2c44b0.96
C9a—C12a1.526 (10)C44b—H3c44b0.96
C9b—C11b1.513 (8)C43b—H1c43b0.96
C9b—C10b1.518 (10)C43b—H2c43b0.96
C9b—C12b1.526 (11)C43b—H3c43b0.96
C17—H1c170.96C45b—H1c45b0.96
C34—C331.381 (3)C45b—H2c45b0.96
C34—C351.379 (2)C45b—H3c45b0.96
C34—H1c340.96C40a—H1c40a0.96
C24—C26a1.550 (6)C40a—H2c40a0.96
C24—C25a1.475 (7)C40a—H3c40a0.96
C24—C27a1.552 (5)C41a—H1c41a0.96
C24—C26b1.508 (8)C41a—H2c41a0.96
C24—C25b1.539 (9)C41a—H3c41a0.96
C24—C27b1.499 (9)C42a—H1c42a0.96
C19—H1c190.96C42a—H2c42a0.96
C4—C51.378 (3)C42a—H3c42a0.96
C4—H1c40.96C40b—H1c40b0.96
C5—C61.374 (3)C40b—H2c40b0.96
C1—C21.398 (2)C40b—H3c40b0.96
C1—C61.390 (3)C41b—H1c41b0.96
C1—C71.504 (3)C41b—H2c41b0.96
C23—C29a1.521 (4)C41b—H3c41b0.96
C23—C28a1.530 (3)C42b—H1c42b0.96
C23—C30a1.536 (3)C42b—H2c42b0.96
C2—H1c20.96C42b—H3c42b0.96
C6—H1c60.96
O4—P1—N3115.50 (9)O3—C7—N2121.03 (18)
O4—P1—N4115.07 (8)O3—C7—C1120.06 (18)
O4—P1—N2105.46 (8)N2—C7—C1118.91 (15)
N3—P1—N4104.82 (7)N9—C35—C34119.28 (19)
N3—P1—N2107.50 (9)N9—C35—C36118.04 (15)
N4—P1—N2108.13 (8)C34—C35—C36122.7 (2)
O8—P2—N8115.23 (9)O11—C37—N10120.59 (17)
O8—P2—N7114.93 (8)O11—C37—C31120.15 (18)
O8—P2—N6105.64 (7)N10—C37—C31119.23 (14)
N8—P2—N7104.58 (7)O7—C22—N6120.57 (17)
N8—P2—N6107.93 (8)O7—C22—C16119.70 (18)
N7—P2—N6108.23 (9)N6—C22—C16119.73 (14)
N11—P3—O12113.73 (9)C31—C32—C33120.2 (2)
N11—P3—N10110.25 (8)C31—C32—H1c32119.881
N11—P3—N12106.55 (8)C33—C32—H1c32119.882
O12—P3—N10106.39 (7)C8—C13a—H1c13a109.471
O12—P3—N12115.46 (9)C8—C13a—H2c13a109.471
N10—P3—N12104.01 (9)C8—C13a—H3c13a109.471
O1—N1—O2124.3 (2)H1c13a—C13a—H2c13a109.471
O1—N1—C5118.44 (16)H1c13a—C13a—H3c13a109.471
O2—N1—C5117.3 (2)H2c13a—C13a—H3c13a109.471
P3—N11—C38128.31 (11)C8—C15a—H1c15a109.471
P3—N11—H1n11115.843C8—C15a—H2c15a109.471
C38—N11—H1n11115.842C8—C15a—H3c15a109.471
O5—N5—O6124.3 (2)H1c15a—C15a—H2c15a109.47
O5—N5—C20i118.21 (17)H1c15a—C15a—H3c15a109.472
O6—N5—C20i117.5 (2)H2c15a—C15a—H3c15a109.471
O10—N9—O9124.1 (2)C8—C14a—H1c14a109.471
O10—N9—C35118.30 (19)C8—C14a—H2c14a109.471
O9—N9—C35117.62 (15)C8—C14a—H3c14a109.471
P2—N8—C24127.10 (11)H1c14a—C14a—H2c14a109.471
P2—N8—H1n8116.447H1c14a—C14a—H3c14a109.471
C24—N8—H1n8116.448H2c14a—C14a—H3c14a109.471
P1—N3—C8129.16 (14)H1c11a—C11a—H2c11a109.472
P1—N3—H1n3115.421H1c11a—C11a—H3c11a109.47
C8—N3—H1n3115.421H2c11a—C11a—H3c11a109.471
P2—N7—C23125.72 (12)H1c10a—C10a—H2c10a109.471
P2—N7—H1n7117.14H1c10a—C10a—H3c10a109.472
C23—N7—H1n7117.14H1c12a—C12a—H2c12a109.471
P2—N6—C22122.49 (11)H1c12a—C12a—H3c12a109.471
P2—N6—H1n6118.755H2c12a—C12a—H3c12a109.471
C22—N6—H1n6118.755H1c11b—C11b—H2c11b109.472
P1—N4—H1n4115.555H1c11b—C11b—H3c11b109.47
P3—N10—C37122.55 (11)H2c11b—C11b—H3c11b109.471
P3—N10—H1n10118.725H1c10b—C10b—H2c10b109.471
C37—N10—H1n10118.725H1c10b—C10b—H3c10b109.472
P1—N2—C7123.35 (12)H2c10b—C10b—H3c10b109.471
P1—N2—H1n2118.327H1c12b—C12b—H2c12b109.471
C7—N2—H1n2118.326H1c12b—C12b—H3c12b109.471
N5i—C20—C19117.8 (2)H2c12b—C12b—H3c12b109.471
N5i—C20—C21119.17 (16)C23—C29a—H1c29a109.471
C19—C20—C21123.0 (2)C23—C29a—H2c29a109.472
C17—C18—C19120.96 (17)C23—C29a—H3c29a109.471
C17—C18—H1c18119.517H1c29a—C29a—H2c29a109.471
C19—C18—H1c18119.518H1c29a—C29a—H3c29a109.471
P3—N12—H1n12113.923H2c29a—C29a—H3c29a109.471
N12—C39a—C40a109.8 (3)C23—C28a—H1c28a109.471
N12—C39a—C41a109.8 (3)C23—C28a—H2c28a109.471
N12—C39a—C42a106.8 (3)C23—C28a—H3c28a109.471
C40a—C39a—C41a109.7 (4)H1c28a—C28a—H2c28a109.471
C40a—C39a—C42a110.4 (4)H1c28a—C28a—H3c28a109.471
C41a—C39a—C42a110.4 (4)H2c28a—C28a—H3c28a109.471
N12—C39b—C40b119.2 (5)C23—C30a—H1c30a109.471
N12—C39b—C41b92.5 (5)C23—C30a—H2c30a109.471
N12—C39b—C42b113.2 (6)C23—C30a—H3c30a109.471
C40b—C39b—C41b109.7 (6)H1c30a—C30a—H2c30a109.472
C40b—C39b—C42b110.4 (6)H1c30a—C30a—H3c30a109.471
C41b—C39b—C42b110.4 (5)H2c30a—C30a—H3c30a109.471
C4—C3—C2120.89 (18)C24—C26a—H1c26a109.472
C4—C3—H1c3119.555C24—C26a—H2c26a109.471
C2—C3—H1c3119.554C24—C26a—H3c26a109.471
N11—C38—C44a108.4 (3)H1c26a—C26a—H2c26a109.471
N11—C38—C43a111.4 (3)H1c26a—C26a—H3c26a109.471
N11—C38—C45a106.9 (3)H2c26a—C26a—H3c26a109.471
N11—C38—C44b106.2 (4)C24—C25a—H1c25a109.471
N11—C38—C43b105.1 (4)C24—C25a—H2c25a109.471
N11—C38—C45b116.7 (5)C24—C25a—H3c25a109.472
C44a—C38—C43a109.2 (5)H1c25a—C25a—H2c25a109.472
C44a—C38—C45a110.5 (4)H1c25a—C25a—H3c25a109.47
C43a—C38—C45a110.4 (4)H2c25a—C25a—H3c25a109.471
C44b—C38—C43b106.0 (6)C24—C27a—H1c27a109.471
C44b—C38—C45b112.1 (6)C24—C27a—H2c27a109.471
C43b—C38—C45b109.9 (6)C24—C27a—H3c27a109.471
C17—C16—C21118.54 (18)H1c27a—C27a—H2c27a109.471
C17—C16—C22123.84 (18)H1c27a—C27a—H3c27a109.471
C21—C16—C22117.61 (15)H2c27a—C27a—H3c27a109.472
C36—C31—C37116.29 (14)C24—C26b—H1c26b108.824
C36—C31—C32119.33 (18)C24—C26b—H2c26b107.481
C37—C31—C32124.35 (18)C24—C26b—H3c26b112.076
N3—C8—C13a105.76 (19)H1c26b—C26b—H2c26b109.471
N3—C8—C15a110.14 (17)H1c26b—C26b—H3c26b109.471
N3—C8—C14a110.49 (16)H2c26b—C26b—H3c26b109.471
C13a—C8—C15a109.89 (17)C24—C25b—H1c25b110.425
C13a—C8—C14a110.2 (2)C24—C25b—H2c25b107.411
C15a—C8—C14a110.2 (2)C24—C25b—H3c25b110.558
N4—C9a—C11a107.2 (4)H1c25b—C25b—H2c25b109.472
N4—C9a—C10a111.7 (5)H1c25b—C25b—H3c25b109.47
N4—C9a—C12a108.3 (5)H2c25b—C25b—H3c25b109.471
C11a—C9a—C10a109.1 (6)C24—C27b—H1c27b111.887
C11a—C9a—C12a110.1 (5)C24—C27b—H2c27b108.129
C10a—C9a—C12a110.5 (5)C24—C27b—H3c27b108.37
N4—C9b—C11b104.5 (5)H1c27b—C27b—H2c27b109.471
N4—C9b—C10b107.9 (5)H1c27b—C27b—H3c27b109.471
N4—C9b—C12b114.6 (5)H2c27b—C27b—H3c27b109.472
C11b—C9b—C10b109.1 (6)C38—C44a—H1c44a109.471
C11b—C9b—C12b110.1 (5)C38—C44a—H2c44a109.471
C10b—C9b—C12b110.5 (5)C38—C44a—H3c44a109.471
C18—C17—C16120.5 (2)H1c44a—C44a—H2c44a109.471
C18—C17—H1c17119.741H1c44a—C44a—H3c44a109.472
C16—C17—H1c17119.741H2c44a—C44a—H3c44a109.47
C33—C34—C35118.3 (2)C38—C43a—H1c43a109.472
C33—C34—H1c34120.858C38—C43a—H2c43a109.471
C35—C34—H1c34120.859C38—C43a—H3c43a109.471
N8—C24—C26a109.6 (2)H1c43a—C43a—H2c43a109.47
N8—C24—C25a107.1 (3)H1c43a—C43a—H3c43a109.472
N8—C24—C27a112.9 (3)H2c43a—C43a—H3c43a109.471
N8—C24—C26b106.8 (3)C38—C45a—H1c45a109.471
N8—C24—C25b111.9 (3)C38—C45a—H2c45a109.471
N8—C24—C27b107.5 (4)C38—C45a—H3c45a109.471
C26a—C24—C25a110.9 (4)H1c45a—C45a—H2c45a109.472
C26a—C24—C27a105.9 (3)H1c45a—C45a—H3c45a109.471
C25a—C24—C27a110.5 (4)H2c45a—C45a—H3c45a109.471
C26b—C24—C25b109.7 (5)C38—C44b—H1c44b110.864
C26b—C24—C27b110.8 (4)C38—C44b—H2c44b107.324
C25b—C24—C27b109.9 (4)C38—C44b—H3c44b110.204
C20—C19—C18117.6 (2)H1c44b—C44b—H2c44b109.471
C20—C19—H1c19121.206H1c44b—C44b—H3c44b109.472
C18—C19—H1c19121.207H2c44b—C44b—H3c44b109.471
C3—C4—C5117.7 (2)C38—C43b—H1c43b108.357
C3—C4—H1c4121.148C38—C43b—H2c43b110.382
C5—C4—H1c4121.147C38—C43b—H3c43b109.668
N1—C5—C4118.2 (2)H1c43b—C43b—H2c43b109.47
N1—C5—C6119.11 (16)H1c43b—C43b—H3c43b109.472
C4—C5—C6122.7 (2)H2c43b—C43b—H3c43b109.471
C2—C1—C6118.66 (18)C38—C45b—H1c45b110.846
C2—C1—C7124.04 (19)C38—C45b—H2c45b108.074
C6—C1—C7117.28 (15)C38—C45b—H3c45b109.482
N7—C23—C29a110.00 (18)H1c45b—C45b—H2c45b109.472
N7—C23—C28a106.04 (16)H1c45b—C45b—H3c45b109.471
N7—C23—C30a111.23 (16)H2c45b—C45b—H3c45b109.471
C29a—C23—C28a109.70 (18)H1c40a—C40a—H2c40a109.471
C29a—C23—C30a110.1 (2)H1c40a—C40a—H3c40a109.471
C28a—C23—C30a109.7 (2)H2c40a—C40a—H3c40a109.471
C3—C2—C1120.4 (2)H1c41a—C41a—H2c41a109.471
C3—C2—H1c2119.799H1c41a—C41a—H3c41a109.47
C1—C2—H1c2119.799H2c41a—C41a—H3c41a109.472
C5—C6—C1119.65 (16)H1c42a—C42a—H2c42a109.471
C5—C6—H1c6120.174H1c42a—C42a—H3c42a109.471
C1—C6—H1c6120.175H2c42a—C42a—H3c42a109.472
C31—C36—C35118.93 (15)H1c40b—C40b—H2c40b109.471
C31—C36—H1c36120.536H1c40b—C40b—H3c40b109.471
C35—C36—H1c36120.535H2c40b—C40b—H3c40b109.471
C34—C33—C32120.53 (17)H1c41b—C41b—H2c41b109.471
C34—C33—H1c33119.734H1c41b—C41b—H3c41b109.47
C32—C33—H1c33119.733H2c41b—C41b—H3c41b109.472
C20—C21—C16119.39 (16)H1c42b—C42b—H2c42b109.471
C20—C21—H1c21120.304H1c42b—C42b—H3c42b109.471
C16—C21—H1c21120.304H2c42b—C42b—H3c42b109.472
Symmetry code: (i) x+1, y+1, z+1.
 

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