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Ruxolitinib {RUX; systematic name: (3R)-3-cyclo­pentyl-3-[4-(7H-pyrrolo­[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propane­nitrile, C17H18N6} is an orally bio­available JAK1/2 inhibitor approved for treating inter­mediate- or high-risk myelofibrosis (MF) and high-risk polycythemia vera (PV). Recent patents claim that RUX can exist in many different forms, information for which is important for the clinical utilization of RUX, especially for the formulation and bio­av­ailability of the drug. But there has been no detailed study on its forms so far. Herein crystals of RUX and its dihydrate (RUX-2H; C17H18N6·2H2O) and phos­phate (RUX-P; systematic name: 4-{1-[(1R)-2-cyano-1-cyclo­pentyl­eth­yl]-1H-pyrazol-4-yl}-7H-pyrrolo­[2,3-d]pyrimidin-3-ium di­hy­dro­gen phos­phate, C17H19N6+·H2PO4) were prepared successfully and their structures studied in detail for the first time. Our study shows that the three crystals of RUX differ in the orientation of the pyrimidine ring relative to the pyrazole ring of the RUX mol­ecule, and in their hy­dro­gen-bond inter­actions. The water mol­ecules in RUX-2H and the di­hy­dro­gen phos­phate anion in RUX-P enrich the hy­dro­gen-bond networks in these forms. The expected proton transfer occurs in RUX phos­phate and the protonated N atom is engaged in a charge-assisted hy­dro­gen bond with the counter-anion. Hydrogen-bonding inter­actions dominate in the crystal packing of the three forms. The detailed conformations and packing of the three forms were com­pared through the calculation of both Hirshfeld surfaces and fingerprint plots.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624006740/oj3020sup1.cif
Contains datablocks rux, rux-2h, rux-p, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624006740/oj3020ruxsup2.hkl
Contains datablock rux

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624006740/oj3020rux-2hsup3.hkl
Contains datablock rux-2h

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624006740/oj3020rux-psup4.hkl
Contains datablock rux-p

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624006740/oj3020ruxsup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624006740/oj3020rux-2hsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624006740/oj3020rux-psup7.cml
Supplementary material

CCDC references: 2357755; 2357754; 2357752

Computing details top

(3R)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (rux) top
Crystal data top
C17H18N6F(000) = 1296
Mr = 306.37Dx = 1.260 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 8.7110 (2) ÅCell parameters from 9807 reflections
b = 19.5857 (4) Åθ = 3.3–68.2°
c = 18.9372 (4) ŵ = 0.64 mm1
β = 90.857 (1)°T = 296 K
V = 3230.53 (12) Å3Needle, colourless
Z = 80.42 × 0.12 × 0.1 mm
Data collection top
Bruker D8 VENTURE
diffractometer
10907 reflections with I > 2σ(I)
ω and φ scansRint = 0.035
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 68.4°, θmin = 2.3°
Tmin = 0.642, Tmax = 0.753h = 1010
44067 measured reflectionsk = 2323
11668 independent reflectionsl = 2222
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0775P)2 + 0.3655P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.46 e Å3
11668 reflectionsΔρmin = 0.26 e Å3
829 parametersAbsolute structure: Flack x determined using 4803 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.01 (11)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.0235 (3)0.34297 (14)0.98134 (17)0.0608 (7)
H1A0.0003230.3007240.9874950.073*
C1A0.0811 (4)0.37074 (17)0.9208 (2)0.0609 (8)
H1AA0.1025380.3462490.8800210.073*
N2A0.0466 (4)0.38666 (15)1.09420 (17)0.0658 (7)
C2A0.1026 (4)0.43904 (16)0.92864 (18)0.0552 (7)
H2A0.1393200.4691680.8949020.066*
N3A0.0103 (3)0.50807 (15)1.10703 (16)0.0624 (7)
C3A0.0579 (3)0.45546 (14)0.99861 (16)0.0466 (6)
N4A0.0578 (3)0.69787 (13)1.00863 (15)0.0539 (6)
C4A0.0093 (3)0.39350 (16)1.02998 (18)0.0528 (7)
N5A0.1398 (3)0.67321 (12)0.95401 (13)0.0478 (5)
C5A0.0517 (5)0.4460 (2)1.1289 (2)0.0699 (9)
H5A0.0893460.4437931.1745380.084*
N6A0.1127 (6)0.6824 (3)0.8057 (4)0.145 (2)
C6A0.0430 (3)0.51378 (16)1.04035 (17)0.0492 (6)
C7A0.0740 (3)0.58304 (15)1.01573 (16)0.0476 (6)
C8A0.0182 (4)0.64369 (16)1.04579 (18)0.0554 (7)
H8A0.0393870.6454401.0867080.067*
C9A0.1508 (3)0.60461 (15)0.95691 (17)0.0505 (6)
H9A0.2012440.5768640.9248660.061*
C10A0.2154 (4)0.72084 (14)0.90629 (16)0.0497 (6)
H10A0.1754230.7666560.9157430.060*
C11A0.1767 (5)0.70318 (19)0.82900 (19)0.0660 (9)
H11A0.2118970.7399900.7990330.079*
H11B0.2322190.6622150.8160880.079*
C12A0.0132 (6)0.6922 (3)0.8156 (3)0.0900 (14)
C13A0.3872 (4)0.72204 (16)0.92029 (16)0.0516 (6)
H13A0.4290860.6772700.9077990.062*
C14A0.4748 (5)0.7764 (2)0.8800 (2)0.0758 (10)
H14A0.4961540.7607340.8325850.091*
H14B0.4151110.8180990.8768800.091*
C15A0.6232 (5)0.7888 (3)0.9208 (3)0.0904 (13)
H15A0.6425600.8373530.9255990.108*
H15B0.7089720.7680250.8967710.108*
C16A0.6014 (5)0.7561 (3)0.9929 (2)0.0822 (12)
H16A0.6648400.7156620.9979120.099*
H16B0.6285140.7879541.0302990.099*
C17A0.4340 (4)0.7377 (2)0.99591 (18)0.0697 (10)
H17A0.3745450.7755281.0141540.084*
H17B0.4188310.6982071.0258720.084*
N1B0.9779 (3)0.65858 (14)0.50235 (18)0.0628 (7)
H1B1.0022920.7002770.4937820.075*
C1B0.9135 (4)0.63499 (17)0.5625 (2)0.0646 (9)
H1BA0.8880990.6622550.6008270.078*
N2B1.0594 (3)0.60673 (15)0.39383 (17)0.0656 (7)
C2B0.8910 (4)0.56667 (17)0.5595 (2)0.0599 (8)
H2B0.8498020.5391630.5944800.072*
N3B1.0232 (3)0.48496 (14)0.38960 (15)0.0584 (6)
C3B0.9433 (3)0.54520 (15)0.49183 (17)0.0492 (6)
N4B0.9287 (3)0.30386 (13)0.50606 (16)0.0567 (6)
C4B0.9971 (3)0.60471 (15)0.45804 (19)0.0538 (7)
N5B0.8374 (3)0.33691 (12)0.55286 (13)0.0479 (5)
C5B1.0672 (5)0.54578 (19)0.3642 (2)0.0668 (9)
H5B1.1092990.5448680.3194090.080*
N6B1.0550 (7)0.3476 (3)0.7169 (4)0.156 (3)
C6B0.9620 (3)0.48437 (15)0.45446 (17)0.0478 (6)
C7B0.9243 (3)0.41745 (14)0.48404 (16)0.0468 (6)
C8B0.9797 (4)0.35318 (16)0.46455 (18)0.0559 (7)
H8B1.0448730.3458940.4268190.067*
C9B0.8325 (3)0.40383 (14)0.54065 (16)0.0497 (6)
H9B0.7767520.4357570.5660230.060*
C10B0.7491 (4)0.29975 (14)0.60584 (15)0.0482 (6)
H10B0.6888730.3335510.6316860.058*
C11B0.8572 (5)0.26493 (17)0.65955 (17)0.0623 (8)
H11C0.7960650.2445490.6964070.075*
H11D0.9114480.2283830.6360180.075*
C12B0.9684 (5)0.3106 (2)0.6918 (3)0.0858 (13)
C13B0.6357 (4)0.24987 (16)0.57170 (15)0.0507 (6)
H13B0.6926010.2124030.5499110.061*
C14B0.5233 (5)0.2205 (3)0.6252 (2)0.0822 (12)
H14C0.5494780.1735940.6363640.099*
H14D0.5260730.2470520.6684330.099*
C15B0.3670 (6)0.2243 (6)0.5908 (4)0.152 (4)
H15C0.3001860.2532060.6184210.183*
H15D0.3218690.1791320.5879780.183*
C16B0.3848 (6)0.2537 (4)0.5175 (4)0.127 (3)
H16C0.3759190.2179790.4822110.153*
H16D0.3061750.2877300.5080150.153*
C17B0.5347 (5)0.2843 (2)0.5159 (2)0.0762 (10)
H17C0.5274210.3328410.5254830.091*
H17D0.5788620.2783910.4695320.091*
N1C0.3464 (4)0.07145 (15)0.76582 (17)0.0656 (7)
H1C0.3416910.0291300.7538590.079*
C1C0.2242 (5)0.1146 (2)0.7704 (2)0.0745 (10)
H1CA0.1225740.1020970.7619970.089*
N2C0.6177 (3)0.07957 (14)0.78667 (15)0.0589 (6)
C2C0.2712 (4)0.1787 (2)0.7890 (2)0.0671 (9)
H2C0.2098410.2170910.7947820.081*
N3C0.6993 (3)0.19311 (14)0.81750 (15)0.0581 (6)
C3C0.4327 (4)0.17461 (17)0.79761 (16)0.0537 (7)
N4C0.4257 (3)0.39835 (14)0.80927 (15)0.0568 (6)
C4C0.4764 (4)0.10579 (15)0.78310 (15)0.0510 (7)
N5C0.5651 (3)0.40124 (12)0.84086 (13)0.0488 (5)
C5C0.7211 (4)0.1269 (2)0.80606 (19)0.0647 (8)
H5C0.8212340.1113350.8123570.078*
N6C0.7231 (5)0.4579 (2)0.68906 (19)0.0893 (11)
C6C0.5537 (4)0.21917 (16)0.81223 (15)0.0507 (7)
C7C0.5329 (4)0.29255 (16)0.81936 (15)0.0505 (6)
C8C0.4065 (4)0.33207 (17)0.79678 (19)0.0607 (8)
H8C0.3188610.3137970.7754140.073*
C9C0.6336 (4)0.33973 (16)0.84666 (16)0.0519 (7)
H9C0.7307310.3309820.8655840.062*
C10C0.6220 (3)0.46888 (15)0.86155 (16)0.0499 (6)
H10C0.5434820.5020870.8471040.060*
C11C0.7685 (5)0.4864 (2)0.82084 (19)0.0686 (9)
H11E0.7934790.5342130.8275400.082*
H11F0.8536470.4593880.8391140.082*
C12C0.7463 (5)0.4724 (2)0.7456 (2)0.0677 (9)
C13C0.6445 (3)0.47615 (16)0.94076 (16)0.0520 (7)
H13C0.7349870.4496690.9553780.062*
C14C0.6674 (5)0.55071 (19)0.9640 (2)0.0680 (9)
H14E0.7749600.5633600.9620250.082*
H14F0.6085360.5813260.9338180.082*
C15C0.6109 (7)0.5539 (3)1.0395 (2)0.0913 (14)
H15E0.6971240.5583131.0721210.110*
H15F0.5439680.5929681.0453600.110*
C16C0.5255 (7)0.4896 (3)1.0538 (2)0.0994 (16)
H16E0.4253800.4997251.0729350.119*
H16F0.5818980.4615301.0874780.119*
C17C0.5086 (5)0.4527 (2)0.9834 (2)0.0789 (11)
H17E0.5109780.4036460.9900610.095*
H17F0.4128300.4650750.9599290.095*
N1D0.6319 (4)0.93258 (16)0.74384 (16)0.0671 (7)
H1D0.6387250.9743900.7573870.081*
C1D0.7516 (5)0.8879 (2)0.7396 (3)0.0804 (11)
H1DA0.8530970.8987580.7505840.096*
N2D0.3616 (3)0.92815 (14)0.71904 (15)0.0583 (6)
C2D0.7034 (4)0.8255 (2)0.7173 (2)0.0719 (10)
H2D0.7629030.7866890.7104980.086*
N3D0.2763 (3)0.81756 (14)0.68095 (15)0.0570 (6)
C3D0.5416 (4)0.83243 (16)0.70646 (16)0.0534 (7)
N4D0.5219 (4)0.60688 (15)0.68219 (19)0.0709 (8)
C4D0.5001 (4)0.90056 (15)0.72327 (15)0.0513 (7)
N5D0.3861 (3)0.61066 (13)0.64707 (13)0.0508 (6)
C5D0.2563 (4)0.88334 (19)0.69560 (19)0.0636 (8)
H5D0.1574470.9002710.6887750.076*
N6D0.1493 (8)0.5419 (2)0.7819 (2)0.1213 (19)
C6D0.4198 (4)0.79050 (16)0.68752 (14)0.0500 (6)
C7D0.4355 (4)0.71652 (15)0.67592 (15)0.0512 (7)
C8D0.5518 (5)0.67172 (19)0.6988 (2)0.0677 (9)
H8D0.6400580.6857540.7229660.081*
C9D0.3309 (4)0.67452 (15)0.64292 (16)0.0519 (7)
H9D0.2387360.6878230.6216130.062*
C10D0.3191 (4)0.54834 (14)0.61708 (16)0.0485 (6)
H10D0.2179860.5596260.5968940.058*
C11D0.2973 (4)0.49458 (15)0.67537 (18)0.0595 (8)
H11G0.2426540.4557010.6556180.071*
H11H0.3972880.4788070.6916180.071*
C12D0.2134 (6)0.5204 (2)0.7350 (2)0.0800 (12)
C13D0.4188 (3)0.52042 (15)0.55824 (16)0.0492 (6)
H13D0.5188980.5074670.5784060.059*
C14D0.3487 (5)0.45843 (18)0.52102 (19)0.0645 (8)
H14G0.3703770.4170570.5475090.077*
H14H0.2383470.4635310.5159960.077*
C15D0.4235 (6)0.4557 (2)0.4489 (2)0.0767 (11)
H15G0.5060320.4224600.4489490.092*
H15H0.3486760.4430580.4127750.092*
C16D0.4859 (7)0.5268 (2)0.4348 (2)0.0886 (13)
H16G0.5964500.5253790.4295480.106*
H16H0.4403450.5454780.3919020.106*
C17D0.4440 (5)0.5699 (2)0.4976 (2)0.0726 (10)
H17G0.3512670.5957600.4876830.087*
H17H0.5262480.6015130.5092470.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0673 (16)0.0324 (13)0.0829 (19)0.0026 (11)0.0093 (14)0.0073 (12)
C1A0.0700 (19)0.0392 (16)0.074 (2)0.0013 (14)0.0100 (16)0.0021 (14)
N2A0.0792 (18)0.0454 (16)0.0732 (18)0.0019 (13)0.0151 (14)0.0198 (13)
C2A0.0599 (17)0.0404 (16)0.0656 (18)0.0034 (12)0.0091 (14)0.0056 (13)
N3A0.0749 (17)0.0492 (16)0.0635 (16)0.0014 (13)0.0149 (13)0.0061 (13)
C3A0.0434 (13)0.0336 (14)0.0631 (16)0.0005 (10)0.0036 (12)0.0071 (12)
N4A0.0675 (15)0.0341 (13)0.0606 (15)0.0043 (10)0.0136 (12)0.0046 (10)
C4A0.0507 (14)0.0381 (15)0.0698 (19)0.0015 (12)0.0052 (13)0.0114 (14)
N5A0.0571 (13)0.0282 (11)0.0583 (14)0.0002 (9)0.0111 (11)0.0007 (10)
C5A0.087 (2)0.059 (2)0.064 (2)0.0026 (18)0.0192 (17)0.0152 (17)
N6A0.102 (3)0.124 (4)0.208 (6)0.016 (3)0.071 (4)0.035 (4)
C6A0.0493 (14)0.0387 (15)0.0598 (17)0.0007 (11)0.0034 (12)0.0063 (12)
C7A0.0524 (14)0.0339 (14)0.0566 (16)0.0017 (11)0.0021 (12)0.0013 (12)
C8A0.0657 (17)0.0404 (16)0.0606 (18)0.0005 (13)0.0133 (14)0.0005 (13)
C9A0.0575 (15)0.0299 (13)0.0646 (18)0.0009 (12)0.0135 (13)0.0021 (12)
C10A0.0647 (16)0.0287 (13)0.0558 (15)0.0015 (11)0.0095 (13)0.0021 (11)
C11A0.083 (2)0.0548 (19)0.0598 (19)0.0058 (17)0.0062 (16)0.0053 (15)
C12A0.097 (3)0.067 (3)0.104 (3)0.009 (2)0.036 (3)0.001 (2)
C13A0.0621 (16)0.0409 (15)0.0520 (15)0.0046 (12)0.0100 (12)0.0025 (12)
C14A0.086 (2)0.074 (3)0.067 (2)0.026 (2)0.0130 (18)0.0113 (18)
C15A0.082 (3)0.089 (3)0.101 (3)0.028 (2)0.028 (2)0.016 (3)
C16A0.075 (2)0.088 (3)0.083 (3)0.020 (2)0.004 (2)0.009 (2)
C17A0.076 (2)0.080 (3)0.0525 (18)0.0173 (19)0.0025 (15)0.0017 (17)
N1B0.0639 (16)0.0308 (12)0.094 (2)0.0033 (11)0.0107 (14)0.0024 (13)
C1B0.070 (2)0.0392 (17)0.085 (2)0.0014 (14)0.0134 (17)0.0081 (16)
N2B0.0761 (17)0.0418 (15)0.0794 (19)0.0030 (13)0.0130 (14)0.0140 (14)
C2B0.0675 (19)0.0377 (16)0.075 (2)0.0048 (13)0.0158 (16)0.0006 (14)
N3B0.0675 (15)0.0431 (15)0.0648 (16)0.0012 (11)0.0105 (12)0.0060 (12)
C3B0.0496 (14)0.0327 (14)0.0655 (17)0.0005 (11)0.0048 (12)0.0047 (12)
N4B0.0711 (15)0.0307 (12)0.0688 (16)0.0046 (11)0.0187 (12)0.0026 (11)
C4B0.0512 (14)0.0304 (14)0.080 (2)0.0000 (11)0.0034 (14)0.0067 (14)
N5B0.0641 (14)0.0261 (11)0.0539 (13)0.0018 (9)0.0115 (11)0.0010 (9)
C5B0.082 (2)0.0504 (19)0.069 (2)0.0056 (16)0.0148 (17)0.0114 (16)
N6B0.129 (4)0.104 (4)0.233 (7)0.003 (3)0.099 (5)0.029 (4)
C6B0.0490 (14)0.0313 (14)0.0634 (17)0.0012 (11)0.0060 (12)0.0053 (12)
C7B0.0539 (14)0.0294 (13)0.0573 (16)0.0012 (11)0.0071 (12)0.0017 (12)
C8B0.0679 (18)0.0360 (16)0.0642 (19)0.0016 (13)0.0193 (15)0.0004 (13)
C9B0.0620 (15)0.0266 (13)0.0607 (17)0.0002 (11)0.0091 (13)0.0034 (12)
C10B0.0673 (17)0.0302 (13)0.0474 (14)0.0007 (11)0.0096 (12)0.0000 (11)
C11B0.089 (2)0.0439 (17)0.0542 (17)0.0003 (15)0.0040 (15)0.0013 (14)
C12B0.084 (3)0.066 (3)0.107 (3)0.011 (2)0.029 (2)0.015 (2)
C13B0.0674 (17)0.0390 (14)0.0459 (14)0.0055 (12)0.0064 (12)0.0021 (11)
C14B0.103 (3)0.083 (3)0.061 (2)0.039 (2)0.020 (2)0.0045 (19)
C15B0.069 (3)0.260 (11)0.129 (5)0.022 (4)0.035 (3)0.028 (6)
C16B0.084 (3)0.101 (4)0.196 (7)0.015 (3)0.035 (4)0.042 (5)
C17B0.090 (3)0.074 (3)0.064 (2)0.009 (2)0.0096 (18)0.0013 (18)
N1C0.0786 (18)0.0400 (14)0.0786 (18)0.0083 (13)0.0076 (14)0.0100 (13)
C1C0.072 (2)0.055 (2)0.098 (3)0.0107 (17)0.0081 (19)0.0091 (19)
N2C0.0770 (17)0.0430 (14)0.0569 (15)0.0049 (13)0.0051 (13)0.0046 (11)
C2C0.0636 (19)0.054 (2)0.084 (2)0.0002 (15)0.0080 (17)0.0096 (18)
N3C0.0657 (15)0.0482 (16)0.0602 (15)0.0009 (12)0.0036 (12)0.0049 (12)
C3C0.0685 (18)0.0437 (17)0.0490 (15)0.0033 (13)0.0092 (13)0.0006 (13)
N4C0.0642 (15)0.0401 (13)0.0658 (16)0.0015 (11)0.0111 (12)0.0045 (12)
C4C0.0759 (19)0.0331 (14)0.0441 (14)0.0082 (13)0.0105 (13)0.0015 (11)
N5C0.0613 (13)0.0338 (12)0.0510 (13)0.0023 (10)0.0050 (10)0.0063 (10)
C5C0.073 (2)0.056 (2)0.0650 (19)0.0014 (16)0.0010 (16)0.0029 (15)
N6C0.131 (3)0.074 (2)0.063 (2)0.023 (2)0.0199 (19)0.0033 (17)
C6C0.0711 (18)0.0416 (16)0.0396 (13)0.0042 (13)0.0043 (12)0.0006 (12)
C7C0.0713 (17)0.0368 (15)0.0436 (14)0.0002 (13)0.0053 (12)0.0008 (11)
C8C0.074 (2)0.0417 (17)0.0662 (19)0.0120 (14)0.0098 (15)0.0062 (14)
C9C0.0669 (17)0.0374 (15)0.0511 (16)0.0059 (13)0.0053 (13)0.0033 (12)
C10C0.0612 (16)0.0357 (14)0.0526 (15)0.0002 (12)0.0033 (12)0.0062 (12)
C11C0.081 (2)0.060 (2)0.065 (2)0.0143 (17)0.0070 (17)0.0056 (16)
C12C0.091 (2)0.0479 (18)0.064 (2)0.0072 (17)0.0163 (17)0.0012 (16)
C13C0.0566 (15)0.0447 (16)0.0545 (16)0.0025 (12)0.0057 (12)0.0066 (13)
C14C0.081 (2)0.052 (2)0.072 (2)0.0070 (16)0.0079 (17)0.0172 (16)
C15C0.123 (4)0.076 (3)0.075 (3)0.005 (3)0.001 (2)0.032 (2)
C16C0.125 (4)0.104 (4)0.070 (2)0.021 (3)0.025 (2)0.026 (3)
C17C0.094 (3)0.076 (3)0.067 (2)0.022 (2)0.0129 (19)0.0160 (19)
N1D0.0804 (19)0.0457 (16)0.0752 (18)0.0108 (13)0.0008 (15)0.0052 (13)
C1D0.074 (2)0.064 (3)0.103 (3)0.0107 (19)0.008 (2)0.003 (2)
N2D0.0769 (17)0.0368 (13)0.0614 (15)0.0022 (12)0.0051 (13)0.0055 (11)
C2D0.064 (2)0.065 (2)0.087 (3)0.0018 (17)0.0007 (17)0.0015 (19)
N3D0.0666 (15)0.0431 (14)0.0611 (15)0.0040 (12)0.0033 (12)0.0058 (11)
C3D0.0726 (19)0.0386 (16)0.0490 (15)0.0022 (13)0.0065 (13)0.0040 (12)
N4D0.0788 (18)0.0386 (14)0.094 (2)0.0026 (13)0.0273 (16)0.0102 (14)
C4D0.0762 (19)0.0334 (14)0.0445 (14)0.0077 (13)0.0060 (13)0.0032 (11)
N5D0.0645 (14)0.0321 (12)0.0556 (13)0.0044 (11)0.0070 (11)0.0041 (10)
C5D0.073 (2)0.0483 (18)0.069 (2)0.0001 (15)0.0002 (16)0.0058 (15)
N6D0.210 (6)0.065 (2)0.091 (3)0.014 (3)0.069 (3)0.002 (2)
C6D0.0690 (17)0.0396 (15)0.0414 (14)0.0008 (13)0.0008 (12)0.0025 (11)
C7D0.0722 (18)0.0345 (15)0.0468 (14)0.0015 (13)0.0015 (13)0.0018 (11)
C8D0.079 (2)0.0480 (19)0.076 (2)0.0072 (16)0.0174 (18)0.0121 (16)
C9D0.0674 (17)0.0350 (14)0.0531 (16)0.0048 (12)0.0007 (13)0.0010 (12)
C10D0.0589 (15)0.0330 (13)0.0536 (15)0.0038 (11)0.0048 (12)0.0040 (11)
C11D0.086 (2)0.0330 (15)0.0603 (17)0.0008 (14)0.0112 (16)0.0040 (12)
C12D0.127 (3)0.0436 (19)0.070 (2)0.000 (2)0.025 (2)0.0003 (16)
C13D0.0543 (15)0.0373 (14)0.0558 (16)0.0050 (11)0.0043 (12)0.0052 (12)
C14D0.082 (2)0.0456 (18)0.0659 (19)0.0000 (15)0.0020 (16)0.0154 (15)
C15D0.114 (3)0.057 (2)0.0597 (19)0.013 (2)0.0016 (19)0.0098 (16)
C16D0.125 (4)0.072 (3)0.069 (2)0.004 (3)0.017 (2)0.003 (2)
C17D0.101 (3)0.0506 (19)0.067 (2)0.0013 (18)0.0105 (19)0.0009 (16)
Geometric parameters (Å, º) top
N1A—H1A0.8600N1C—H1C0.8600
N1A—C1A1.371 (5)N1C—C1C1.364 (5)
N1A—C4A1.359 (5)N1C—C4C1.353 (4)
C1A—H1AA0.9300C1C—H1CA0.9300
C1A—C2A1.358 (5)C1C—C2C1.364 (6)
N2A—C4A1.323 (4)N2C—C4C1.335 (4)
N2A—C5A1.336 (5)N2C—C5C1.339 (5)
C2A—H2A0.9300C2C—H2C0.9300
C2A—C3A1.424 (5)C2C—C3C1.416 (5)
N3A—C5A1.336 (5)N3C—C5C1.329 (5)
N3A—C6A1.356 (4)N3C—C6C1.370 (4)
C3A—C4A1.419 (4)C3C—C4C1.428 (4)
C3A—C6A1.396 (4)C3C—C6C1.393 (5)
N4A—N5A1.355 (4)N4C—N5C1.346 (4)
N4A—C8A1.322 (4)N4C—C8C1.330 (4)
N5A—C9A1.348 (4)N5C—C9C1.348 (4)
N5A—C10A1.463 (4)N5C—C10C1.466 (4)
C5A—H5A0.9300C5C—H5C0.9300
N6A—C12A1.126 (7)N6C—C12C1.123 (5)
C6A—C7A1.461 (4)C6C—C7C1.455 (4)
C7A—C8A1.407 (4)C7C—C8C1.407 (5)
C7A—C9A1.374 (4)C7C—C9C1.370 (5)
C8A—H8A0.9300C8C—H8C0.9300
C9A—H9A0.9300C9C—H9C0.9300
C10A—H10A0.9800C10C—H10C0.9800
C10A—C11A1.536 (5)C10C—C11C1.539 (5)
C10A—C13A1.516 (4)C10C—C13C1.516 (4)
C11A—H11A0.9700C11C—H11E0.9700
C11A—H11B0.9700C11C—H11F0.9700
C11A—C12A1.459 (6)C11C—C12C1.461 (5)
C13A—H13A0.9800C13C—H13C0.9800
C13A—C14A1.521 (5)C13C—C14C1.538 (5)
C13A—C17A1.515 (4)C13C—C17C1.514 (5)
C14A—H14A0.9700C14C—H14E0.9700
C14A—H14B0.9700C14C—H14F0.9700
C14A—C15A1.515 (6)C14C—C15C1.520 (6)
C15A—H15A0.9700C15C—H15E0.9700
C15A—H15B0.9700C15C—H15F0.9700
C15A—C16A1.523 (7)C15C—C16C1.489 (8)
C16A—H16A0.9700C16C—H16E0.9700
C16A—H16B0.9700C16C—H16F0.9700
C16A—C17A1.504 (5)C16C—C17C1.521 (6)
C17A—H17A0.9700C17C—H17E0.9700
C17A—H17B0.9700C17C—H17F0.9700
N1B—H1B0.8600N1D—H1D0.8600
N1B—C1B1.359 (5)N1D—C1D1.365 (6)
N1B—C4B1.360 (5)N1D—C4D1.360 (4)
C1B—H1BA0.9300C1D—H1DA0.9300
C1B—C2B1.353 (5)C1D—C2D1.357 (6)
N2B—C4B1.340 (5)N2D—C4D1.323 (4)
N2B—C5B1.321 (5)N2D—C5D1.340 (5)
C2B—H2B0.9300C2D—H2D0.9300
C2B—C3B1.430 (5)C2D—C3D1.428 (5)
N3B—C5B1.342 (4)N3D—C5D1.330 (5)
N3B—C6B1.346 (4)N3D—C6D1.362 (4)
C3B—C4B1.413 (4)C3D—C4D1.420 (4)
C3B—C6B1.396 (4)C3D—C6D1.384 (5)
N4B—N5B1.363 (4)N4D—N5D1.350 (4)
N4B—C8B1.326 (4)N4D—C8D1.333 (5)
N5B—C9B1.332 (4)N5D—C9D1.342 (4)
N5B—C10B1.467 (4)N5D—C10D1.464 (4)
C5B—H5B0.9300C5D—H5D0.9300
N6B—C12B1.145 (7)N6D—C12D1.136 (6)
C6B—C7B1.465 (4)C6D—C7D1.472 (4)
C7B—C8B1.400 (4)C7D—C8D1.404 (5)
C7B—C9B1.373 (4)C7D—C9D1.371 (5)
C8B—H8B0.9300C8D—H8D0.9300
C9B—H9B0.9300C9D—H9D0.9300
C10B—H10B0.9800C10D—H10D0.9800
C10B—C11B1.535 (4)C10D—C11D1.539 (4)
C10B—C13B1.526 (4)C10D—C13D1.525 (4)
C11B—H11C0.9700C11D—H11G0.9700
C11B—H11D0.9700C11D—H11H0.9700
C11B—C12B1.446 (6)C11D—C12D1.446 (5)
C13B—H13B0.9800C13D—H13D0.9800
C13B—C14B1.531 (5)C13D—C14D1.527 (4)
C13B—C17B1.523 (5)C13D—C17D1.520 (5)
C14B—H14C0.9700C14D—H14G0.9700
C14B—H14D0.9700C14D—H14H0.9700
C14B—C15B1.502 (8)C14D—C15D1.523 (5)
C15B—H15C0.9700C15D—H15G0.9700
C15B—H15D0.9700C15D—H15H0.9700
C15B—C16B1.514 (9)C15D—C16D1.520 (6)
C16B—H16C0.9700C16D—H16G0.9700
C16B—H16D0.9700C16D—H16H0.9700
C16B—C17B1.438 (7)C16D—C17D1.507 (6)
C17B—H17C0.9700C17D—H17G0.9700
C17B—H17D0.9700C17D—H17H0.9700
C1A—N1A—H1A125.8C1C—N1C—H1C125.4
C4A—N1A—H1A125.8C4C—N1C—H1C125.4
C4A—N1A—C1A108.4 (3)C4C—N1C—C1C109.1 (3)
N1A—C1A—H1AA124.7N1C—C1C—H1CA124.6
C2A—C1A—N1A110.5 (3)N1C—C1C—C2C110.8 (3)
C2A—C1A—H1AA124.7C2C—C1C—H1CA124.6
C4A—N2A—C5A112.3 (3)C4C—N2C—C5C111.3 (3)
C1A—C2A—H2A126.7C1C—C2C—H2C127.1
C1A—C2A—C3A106.6 (3)C1C—C2C—C3C105.8 (3)
C3A—C2A—H2A126.7C3C—C2C—H2C127.1
C5A—N3A—C6A117.5 (3)C5C—N3C—C6C119.1 (3)
C4A—C3A—C2A106.5 (3)C2C—C3C—C4C107.3 (3)
C6A—C3A—C2A137.8 (3)C6C—C3C—C2C137.3 (3)
C6A—C3A—C4A115.6 (3)C6C—C3C—C4C115.2 (3)
C8A—N4A—N5A105.4 (2)C8C—N4C—N5C103.3 (3)
N1A—C4A—C3A108.0 (3)N1C—C4C—C3C106.9 (3)
N2A—C4A—N1A126.0 (3)N2C—C4C—N1C126.1 (3)
N2A—C4A—C3A126.0 (3)N2C—C4C—C3C127.0 (3)
N4A—N5A—C10A119.5 (2)N4C—N5C—C9C113.2 (2)
C9A—N5A—N4A111.2 (2)N4C—N5C—C10C117.1 (2)
C9A—N5A—C10A129.0 (2)C9C—N5C—C10C129.7 (3)
N2A—C5A—H5A115.5N2C—C5C—H5C115.7
N3A—C5A—N2A128.9 (3)N3C—C5C—N2C128.5 (4)
N3A—C5A—H5A115.5N3C—C5C—H5C115.7
N3A—C6A—C3A119.7 (3)N3C—C6C—C3C118.6 (3)
N3A—C6A—C7A116.2 (3)N3C—C6C—C7C118.6 (3)
C3A—C6A—C7A124.0 (3)C3C—C6C—C7C122.8 (3)
C8A—C7A—C6A126.0 (3)C8C—C7C—C6C127.8 (3)
C9A—C7A—C6A129.7 (3)C9C—C7C—C6C128.4 (3)
C9A—C7A—C8A104.1 (3)C9C—C7C—C8C103.7 (3)
N4A—C8A—C7A111.6 (3)N4C—C8C—C7C112.8 (3)
N4A—C8A—H8A124.2N4C—C8C—H8C123.6
C7A—C8A—H8A124.2C7C—C8C—H8C123.6
N5A—C9A—C7A107.7 (3)N5C—C9C—C7C107.0 (3)
N5A—C9A—H9A126.1N5C—C9C—H9C126.5
C7A—C9A—H9A126.1C7C—C9C—H9C126.5
N5A—C10A—H10A107.9N5C—C10C—H10C107.0
N5A—C10A—C11A110.5 (3)N5C—C10C—C11C110.3 (3)
N5A—C10A—C13A110.8 (2)N5C—C10C—C13C112.8 (3)
C11A—C10A—H10A107.9C11C—C10C—H10C107.0
C13A—C10A—H10A107.9C13C—C10C—H10C107.0
C13A—C10A—C11A111.8 (3)C13C—C10C—C11C112.3 (3)
C10A—C11A—H11A108.9C10C—C11C—H11E109.6
C10A—C11A—H11B108.9C10C—C11C—H11F109.6
H11A—C11A—H11B107.7H11E—C11C—H11F108.1
C12A—C11A—C10A113.5 (3)C12C—C11C—C10C110.4 (3)
C12A—C11A—H11A108.9C12C—C11C—H11E109.6
C12A—C11A—H11B108.9C12C—C11C—H11F109.6
N6A—C12A—C11A178.5 (6)N6C—C12C—C11C175.2 (5)
C10A—C13A—H13A108.3C10C—C13C—H13C108.7
C10A—C13A—C14A115.1 (3)C10C—C13C—C14C112.7 (3)
C14A—C13A—H13A108.3C14C—C13C—H13C108.7
C17A—C13A—C10A114.8 (3)C17C—C13C—C10C114.1 (3)
C17A—C13A—H13A108.3C17C—C13C—H13C108.7
C17A—C13A—C14A101.7 (3)C17C—C13C—C14C103.6 (3)
C13A—C14A—H14A110.4C13C—C14C—H14E110.7
C13A—C14A—H14B110.4C13C—C14C—H14F110.7
H14A—C14A—H14B108.6H14E—C14C—H14F108.8
C15A—C14A—C13A106.7 (3)C15C—C14C—C13C105.4 (3)
C15A—C14A—H14A110.4C15C—C14C—H14E110.7
C15A—C14A—H14B110.4C15C—C14C—H14F110.7
C14A—C15A—H15A110.6C14C—C15C—H15E110.1
C14A—C15A—H15B110.6C14C—C15C—H15F110.1
C14A—C15A—C16A105.8 (3)H15E—C15C—H15F108.4
H15A—C15A—H15B108.7C16C—C15C—C14C107.9 (3)
C16A—C15A—H15A110.6C16C—C15C—H15E110.1
C16A—C15A—H15B110.6C16C—C15C—H15F110.1
C15A—C16A—H16A110.6C15C—C16C—H16E110.4
C15A—C16A—H16B110.6C15C—C16C—H16F110.4
H16A—C16A—H16B108.8C15C—C16C—C17C106.5 (4)
C17A—C16A—C15A105.6 (3)H16E—C16C—H16F108.6
C17A—C16A—H16A110.6C17C—C16C—H16E110.4
C17A—C16A—H16B110.6C17C—C16C—H16F110.4
C13A—C17A—H17A110.7C13C—C17C—C16C104.9 (3)
C13A—C17A—H17B110.7C13C—C17C—H17E110.8
C16A—C17A—C13A105.1 (3)C13C—C17C—H17F110.8
C16A—C17A—H17A110.7C16C—C17C—H17E110.8
C16A—C17A—H17B110.7C16C—C17C—H17F110.8
H17A—C17A—H17B108.8H17E—C17C—H17F108.8
C1B—N1B—H1B126.0C1D—N1D—H1D125.4
C1B—N1B—C4B108.0 (3)C4D—N1D—H1D125.4
C4B—N1B—H1B126.0C4D—N1D—C1D109.3 (3)
N1B—C1B—H1BA124.4N1D—C1D—H1DA124.4
C2B—C1B—N1B111.2 (3)C2D—C1D—N1D111.3 (4)
C2B—C1B—H1BA124.4C2D—C1D—H1DA124.4
C5B—N2B—C4B112.5 (3)C4D—N2D—C5D111.8 (3)
C1B—C2B—H2B126.8C1D—C2D—H2D127.5
C1B—C2B—C3B106.3 (3)C1D—C2D—C3D105.0 (4)
C3B—C2B—H2B126.8C3D—C2D—H2D127.5
C5B—N3B—C6B116.9 (3)C5D—N3D—C6D118.7 (3)
C4B—C3B—C2B106.0 (3)C4D—C3D—C2D108.1 (3)
C6B—C3B—C2B138.3 (3)C6D—C3D—C2D137.0 (3)
C6B—C3B—C4B115.6 (3)C6D—C3D—C4D114.8 (3)
C8B—N4B—N5B104.1 (2)C8D—N4D—N5D103.3 (3)
N1B—C4B—C3B108.4 (3)N1D—C4D—C3D106.3 (3)
N2B—C4B—N1B126.3 (3)N2D—C4D—N1D126.4 (3)
N2B—C4B—C3B125.2 (3)N2D—C4D—C3D127.2 (3)
N4B—N5B—C10B121.8 (2)N4D—N5D—C10D119.1 (2)
C9B—N5B—N4B111.8 (2)C9D—N5D—N4D113.0 (3)
C9B—N5B—C10B126.3 (2)C9D—N5D—C10D127.8 (3)
N2B—C5B—N3B129.3 (3)N2D—C5D—H5D116.1
N2B—C5B—H5B115.3N3D—C5D—N2D127.8 (3)
N3B—C5B—H5B115.3N3D—C5D—H5D116.1
N3B—C6B—C3B120.4 (3)N3D—C6D—C3D119.4 (3)
N3B—C6B—C7B116.8 (3)N3D—C6D—C7D117.1 (3)
C3B—C6B—C7B122.8 (3)C3D—C6D—C7D123.4 (3)
C8B—C7B—C6B128.6 (3)C8D—C7D—C6D129.6 (3)
C9B—C7B—C6B127.5 (3)C9D—C7D—C6D126.6 (3)
C9B—C7B—C8B103.8 (3)C9D—C7D—C8D103.8 (3)
N4B—C8B—C7B112.3 (3)N4D—C8D—C7D112.6 (3)
N4B—C8B—H8B123.9N4D—C8D—H8D123.7
C7B—C8B—H8B123.9C7D—C8D—H8D123.7
N5B—C9B—C7B108.0 (3)N5D—C9D—C7D107.3 (3)
N5B—C9B—H9B126.0N5D—C9D—H9D126.4
C7B—C9B—H9B126.0C7D—C9D—H9D126.4
N5B—C10B—H10B107.2N5D—C10D—H10D108.3
N5B—C10B—C11B110.5 (3)N5D—C10D—C11D110.2 (2)
N5B—C10B—C13B111.7 (2)N5D—C10D—C13D110.7 (3)
C11B—C10B—H10B107.2C11D—C10D—H10D108.3
C13B—C10B—H10B107.2C13D—C10D—H10D108.3
C13B—C10B—C11B112.5 (2)C13D—C10D—C11D110.9 (2)
C10B—C11B—H11C108.8C10D—C11D—H11G109.0
C10B—C11B—H11D108.8C10D—C11D—H11H109.0
H11C—C11B—H11D107.7H11G—C11D—H11H107.8
C12B—C11B—C10B113.9 (3)C12D—C11D—C10D112.9 (3)
C12B—C11B—H11C108.8C12D—C11D—H11G109.0
C12B—C11B—H11D108.8C12D—C11D—H11H109.0
N6B—C12B—C11B178.9 (5)N6D—C12D—C11D178.6 (5)
C10B—C13B—H13B109.3C10D—C13D—H13D108.7
C10B—C13B—C14B112.1 (3)C10D—C13D—C14D113.2 (3)
C14B—C13B—H13B109.3C14D—C13D—H13D108.7
C17B—C13B—C10B112.0 (3)C17D—C13D—C10D114.4 (3)
C17B—C13B—H13B109.3C17D—C13D—H13D108.7
C17B—C13B—C14B104.9 (3)C17D—C13D—C14D102.7 (3)
C13B—C14B—H14C110.5C13D—C14D—H14G110.6
C13B—C14B—H14D110.5C13D—C14D—H14H110.6
H14C—C14B—H14D108.7H14G—C14D—H14H108.8
C15B—C14B—C13B106.2 (4)C15D—C14D—C13D105.6 (3)
C15B—C14B—H14C110.5C15D—C14D—H14G110.6
C15B—C14B—H14D110.5C15D—C14D—H14H110.6
C14B—C15B—H15C110.1C14D—C15D—H15G110.4
C14B—C15B—H15D110.1C14D—C15D—H15H110.4
C14B—C15B—C16B108.2 (4)H15G—C15D—H15H108.6
H15C—C15B—H15D108.4C16D—C15D—C14D106.5 (3)
C16B—C15B—H15C110.1C16D—C15D—H15G110.4
C16B—C15B—H15D110.1C16D—C15D—H15H110.4
C15B—C16B—H16C110.4C15D—C16D—H16G110.4
C15B—C16B—H16D110.4C15D—C16D—H16H110.4
H16C—C16B—H16D108.6H16G—C16D—H16H108.6
C17B—C16B—C15B106.5 (5)C17D—C16D—C15D106.4 (4)
C17B—C16B—H16C110.4C17D—C16D—H16G110.4
C17B—C16B—H16D110.4C17D—C16D—H16H110.4
C13B—C17B—H17C110.0C13D—C17D—H17G110.5
C13B—C17B—H17D110.0C13D—C17D—H17H110.5
C16B—C17B—C13B108.4 (4)C16D—C17D—C13D106.2 (3)
C16B—C17B—H17C110.0C16D—C17D—H17G110.5
C16B—C17B—H17D110.0C16D—C17D—H17H110.5
H17C—C17B—H17D108.4H17G—C17D—H17H108.7
N1A—C1A—C2A—C3A0.8 (4)N1C—C1C—C2C—C3C1.0 (5)
C1A—N1A—C4A—N2A177.9 (3)C1C—N1C—C4C—N2C177.8 (3)
C1A—N1A—C4A—C3A0.7 (4)C1C—N1C—C4C—C3C1.4 (4)
C1A—C2A—C3A—C4A0.3 (4)C1C—C2C—C3C—C4C0.1 (4)
C1A—C2A—C3A—C6A176.3 (3)C1C—C2C—C3C—C6C176.0 (4)
C2A—C3A—C4A—N1A0.3 (3)C2C—C3C—C4C—N1C0.8 (4)
C2A—C3A—C4A—N2A177.5 (3)C2C—C3C—C4C—N2C178.4 (3)
C2A—C3A—C6A—N3A177.8 (3)C2C—C3C—C6C—N3C178.8 (4)
C2A—C3A—C6A—C7A1.2 (5)C2C—C3C—C6C—C7C3.7 (6)
N3A—C6A—C7A—C8A17.7 (5)N3C—C6C—C7C—C8C160.4 (3)
N3A—C6A—C7A—C9A168.0 (3)N3C—C6C—C7C—C9C16.5 (5)
C3A—C6A—C7A—C8A159.1 (3)C3C—C6C—C7C—C8C17.1 (5)
C3A—C6A—C7A—C9A15.2 (5)C3C—C6C—C7C—C9C166.0 (3)
N4A—N5A—C9A—C7A0.3 (4)N4C—N5C—C9C—C7C1.9 (4)
N4A—N5A—C10A—C11A130.0 (3)N4C—N5C—C10C—C11C116.9 (3)
N4A—N5A—C10A—C13A105.5 (3)N4C—N5C—C10C—C13C116.7 (3)
C4A—N1A—C1A—C2A1.0 (4)C4C—N1C—C1C—C2C1.6 (5)
C4A—N2A—C5A—N3A0.6 (6)C4C—N2C—C5C—N3C3.7 (5)
C4A—C3A—C6A—N3A2.1 (4)C4C—C3C—C6C—N3C5.5 (4)
C4A—C3A—C6A—C7A174.6 (3)C4C—C3C—C6C—C7C172.0 (3)
N5A—N4A—C8A—C7A0.0 (4)N5C—N4C—C8C—C7C0.7 (4)
N5A—C10A—C11A—C12A48.1 (4)N5C—C10C—C11C—C12C47.8 (4)
N5A—C10A—C13A—C14A172.6 (3)N5C—C10C—C13C—C14C166.6 (3)
N5A—C10A—C13A—C17A55.1 (3)N5C—C10C—C13C—C17C48.9 (4)
C5A—N2A—C4A—N1A177.5 (3)C5C—N2C—C4C—N1C179.3 (3)
C5A—N2A—C4A—C3A0.8 (5)C5C—N2C—C4C—C3C0.3 (4)
C5A—N3A—C6A—C3A2.4 (5)C5C—N3C—C6C—C3C2.4 (5)
C5A—N3A—C6A—C7A174.6 (3)C5C—N3C—C6C—C7C175.2 (3)
C6A—N3A—C5A—N2A1.0 (6)C6C—N3C—C5C—N2C2.8 (6)
C6A—C3A—C4A—N1A176.7 (3)C6C—C3C—C4C—N1C176.1 (3)
C6A—C3A—C4A—N2A0.5 (5)C6C—C3C—C4C—N2C4.7 (5)
C6A—C7A—C8A—N4A175.6 (3)C6C—C7C—C8C—N4C177.9 (3)
C6A—C7A—C9A—N5A175.5 (3)C6C—C7C—C9C—N5C178.7 (3)
C8A—N4A—N5A—C9A0.2 (4)C8C—N4C—N5C—C9C1.6 (4)
C8A—N4A—N5A—C10A173.5 (3)C8C—N4C—N5C—C10C179.7 (3)
C8A—C7A—C9A—N5A0.3 (3)C8C—C7C—C9C—N5C1.3 (3)
C9A—N5A—C10A—C11A57.5 (4)C9C—N5C—C10C—C11C60.9 (4)
C9A—N5A—C10A—C13A67.0 (4)C9C—N5C—C10C—C13C65.5 (4)
C9A—C7A—C8A—N4A0.2 (4)C9C—C7C—C8C—N4C0.4 (4)
C10A—N5A—C9A—C7A172.7 (3)C10C—N5C—C9C—C7C179.7 (3)
C10A—C13A—C14A—C15A157.6 (3)C10C—C13C—C14C—C15C153.0 (3)
C10A—C13A—C17A—C16A164.1 (3)C10C—C13C—C17C—C16C157.6 (4)
C11A—C10A—C13A—C14A63.6 (4)C11C—C10C—C13C—C14C68.0 (4)
C11A—C10A—C13A—C17A178.8 (3)C11C—C10C—C13C—C17C174.2 (3)
C13A—C10A—C11A—C12A172.0 (3)C13C—C10C—C11C—C12C174.5 (3)
C13A—C14A—C15A—C16A14.5 (5)C13C—C14C—C15C—C16C12.7 (5)
C14A—C13A—C17A—C16A39.2 (4)C14C—C13C—C17C—C16C34.7 (5)
C14A—C15A—C16A—C17A10.0 (5)C14C—C15C—C16C—C17C8.9 (6)
C15A—C16A—C17A—C13A31.0 (5)C15C—C16C—C17C—C13C27.4 (6)
C17A—C13A—C14A—C15A32.9 (4)C17C—C13C—C14C—C15C29.2 (4)
N1B—C1B—C2B—C3B0.8 (4)N1D—C1D—C2D—C3D0.4 (5)
C1B—N1B—C4B—N2B178.8 (3)C1D—N1D—C4D—N2D178.4 (3)
C1B—N1B—C4B—C3B0.3 (4)C1D—N1D—C4D—C3D0.8 (4)
C1B—C2B—C3B—C4B0.6 (4)C1D—C2D—C3D—C4D0.1 (4)
C1B—C2B—C3B—C6B176.2 (4)C1D—C2D—C3D—C6D176.5 (4)
C2B—C3B—C4B—N1B0.2 (3)C2D—C3D—C4D—N1D0.5 (4)
C2B—C3B—C4B—N2B178.4 (3)C2D—C3D—C4D—N2D178.7 (3)
C2B—C3B—C6B—N3B177.4 (4)C2D—C3D—C6D—N3D178.4 (4)
C2B—C3B—C6B—C7B0.4 (6)C2D—C3D—C6D—C7D3.5 (6)
N3B—C6B—C7B—C8B19.7 (5)N3D—C6D—C7D—C8D158.4 (3)
N3B—C6B—C7B—C9B164.6 (3)N3D—C6D—C7D—C9D17.1 (5)
C3B—C6B—C7B—C8B157.3 (3)C3D—C6D—C7D—C8D19.6 (5)
C3B—C6B—C7B—C9B18.4 (5)C3D—C6D—C7D—C9D164.9 (3)
N4B—N5B—C9B—C7B0.5 (4)N4D—N5D—C9D—C7D1.0 (4)
N4B—N5B—C10B—C11B66.1 (4)N4D—N5D—C10D—C11D57.4 (4)
N4B—N5B—C10B—C13B60.1 (4)N4D—N5D—C10D—C13D65.7 (4)
C4B—N1B—C1B—C2B0.7 (4)C4D—N1D—C1D—C2D0.8 (5)
C4B—N2B—C5B—N3B0.3 (6)C4D—N2D—C5D—N3D3.6 (5)
C4B—C3B—C6B—N3B2.0 (4)C4D—C3D—C6D—N3D5.1 (4)
C4B—C3B—C6B—C7B174.9 (3)C4D—C3D—C6D—C7D172.9 (3)
N5B—N4B—C8B—C7B0.6 (4)N5D—N4D—C8D—C7D1.1 (5)
N5B—C10B—C11B—C12B53.0 (4)N5D—C10D—C11D—C12D52.5 (4)
N5B—C10B—C13B—C14B169.6 (3)N5D—C10D—C13D—C14D175.6 (3)
N5B—C10B—C13B—C17B52.0 (4)N5D—C10D—C13D—C17D58.4 (3)
C5B—N2B—C4B—N1B177.9 (3)C5D—N2D—C4D—N1D178.7 (3)
C5B—N2B—C4B—C3B0.5 (5)C5D—N2D—C4D—C3D0.3 (5)
C5B—N3B—C6B—C3B1.4 (4)C5D—N3D—C6D—C3D2.5 (5)
C5B—N3B—C6B—C7B175.7 (3)C5D—N3D—C6D—C7D175.6 (3)
C6B—N3B—C5B—N2B0.1 (6)C6D—N3D—C5D—N2D2.3 (6)
C6B—C3B—C4B—N1B177.0 (3)C6D—C3D—C4D—N1D176.9 (3)
C6B—C3B—C4B—N2B1.6 (5)C6D—C3D—C4D—N2D3.9 (5)
C6B—C7B—C8B—N4B175.7 (3)C6D—C7D—C8D—N4D175.7 (4)
C6B—C7B—C9B—N5B175.8 (3)C6D—C7D—C9D—N5D176.7 (3)
C8B—N4B—N5B—C9B0.0 (4)C8D—N4D—N5D—C9D1.3 (4)
C8B—N4B—N5B—C10B175.8 (3)C8D—N4D—N5D—C10D177.1 (3)
C8B—C7B—C9B—N5B0.8 (3)C8D—C7D—C9D—N5D0.2 (4)
C9B—N5B—C10B—C11B118.7 (3)C9D—N5D—C10D—C11D124.5 (3)
C9B—N5B—C10B—C13B115.2 (3)C9D—N5D—C10D—C13D112.5 (3)
C9B—C7B—C8B—N4B0.9 (4)C9D—C7D—C8D—N4D0.6 (4)
C10B—N5B—C9B—C7B176.2 (3)C10D—N5D—C9D—C7D177.2 (3)
C10B—C13B—C14B—C15B134.5 (5)C10D—C13D—C14D—C15D157.6 (3)
C10B—C13B—C17B—C16B145.1 (5)C10D—C13D—C17D—C16D157.8 (3)
C11B—C10B—C13B—C14B65.4 (4)C11D—C10D—C13D—C14D61.8 (3)
C11B—C10B—C13B—C17B177.1 (3)C11D—C10D—C13D—C17D179.0 (3)
C13B—C10B—C11B—C12B178.7 (3)C13D—C10D—C11D—C12D175.5 (3)
C13B—C14B—C15B—C16B1.3 (8)C13D—C14D—C15D—C16D20.4 (4)
C14B—C13B—C17B—C16B23.3 (5)C14D—C13D—C17D—C16D34.7 (4)
C14B—C15B—C16B—C17B15.9 (9)C14D—C15D—C16D—C17D1.1 (5)
C15B—C16B—C17B—C13B24.3 (7)C15D—C16D—C17D—C13D22.5 (5)
C17B—C13B—C14B—C15B12.8 (6)C17D—C13D—C14D—C15D33.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N4Ai0.862.082.935 (4)174
N1B—H1B···N4Bii0.862.122.965 (4)169
N1C—H1C···N2Diii0.862.092.947 (4)172
N1D—H1D···N2Civ0.862.142.994 (4)171
Symmetry codes: (i) x, y1/2, z+2; (ii) x+2, y+1/2, z+1; (iii) x, y1, z; (iv) x, y+1, z.
(3R)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile dihydrate (rux-2h) top
Crystal data top
C17H18N6·2H2ODx = 1.274 Mg m3
Mr = 342.40Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 9790 reflections
a = 9.9563 (7) Åθ = 2.9–68.4°
b = 15.1596 (10) ŵ = 0.72 mm1
c = 23.6491 (16) ÅT = 296 K
V = 3569.4 (4) Å3Block, colourless
Z = 80.47 × 0.28 × 0.23 mm
F(000) = 1456
Data collection top
Bruker D8 VENTURE
diffractometer
6310 reflections with I > 2σ(I)
ω and φ scansRint = 0.054
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 68.6°, θmin = 3.5°
Tmin = 0.512, Tmax = 0.753h = 1211
30745 measured reflectionsk = 1818
6516 independent reflectionsl = 2328
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0873P)2 + 0.4645P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.35 e Å3
6516 reflectionsΔρmin = 0.28 e Å3
475 parametersAbsolute structure: Flack x determined using 2677 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
8 restraintsAbsolute structure parameter: 0.12 (8)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5699 (2)0.59380 (16)0.45379 (10)0.0594 (5)
N1A0.0605 (3)0.78564 (16)0.45821 (10)0.0542 (6)
H1A0.0645890.8197480.4872140.065*
C1A0.0520 (3)0.7429 (2)0.43869 (13)0.0555 (7)
H1AA0.1363250.7465780.4554580.067*
N2A0.2906 (3)0.79140 (16)0.42911 (10)0.0530 (6)
C2A0.0244 (3)0.69514 (18)0.39215 (12)0.0478 (6)
H2A0.0845190.6613760.3712340.057*
N3A0.3408 (2)0.69824 (16)0.34967 (10)0.0491 (5)
C3A0.1155 (3)0.70662 (15)0.38131 (10)0.0387 (5)
N4A0.1937 (2)0.51919 (16)0.22384 (10)0.0510 (5)
C4A0.1633 (3)0.76444 (16)0.42367 (11)0.0448 (6)
N5A0.0651 (2)0.54710 (14)0.22966 (9)0.0450 (5)
C5A0.3722 (3)0.7549 (2)0.39135 (13)0.0539 (7)
H5A0.4622500.7705610.3940680.065*
N6A0.0997 (4)0.3516 (2)0.28628 (16)0.0828 (10)
C6A0.2113 (3)0.67495 (15)0.34305 (10)0.0386 (5)
C7A0.1760 (3)0.61685 (16)0.29573 (11)0.0404 (5)
C8A0.0517 (3)0.60502 (16)0.27195 (11)0.0440 (5)
H8A0.0275420.6323360.2831830.053*
C9A0.2612 (3)0.56179 (18)0.26402 (11)0.0468 (6)
H9A0.3529790.5559150.2703160.056*
C10A0.0391 (3)0.51916 (18)0.18949 (11)0.0471 (6)
H10A0.1255550.5410960.2034360.057*
C11A0.0470 (4)0.4180 (2)0.18736 (13)0.0577 (7)
H11A0.1168910.4006470.1610430.069*
H11B0.0375930.3948020.1734840.069*
C12A0.0756 (3)0.3798 (2)0.24291 (15)0.0602 (7)
C13A0.0152 (3)0.55943 (19)0.13154 (12)0.0536 (7)
H13A0.0704910.5374770.1167790.064*
C14A0.1259 (4)0.5395 (2)0.08832 (14)0.0693 (9)
H14A0.1111950.4825300.0706440.083*
H14B0.2134710.5393920.1062690.083*
C15A0.1160 (7)0.6124 (3)0.0455 (2)0.1029 (17)
H15A0.2050680.6312640.0341820.123*
H15B0.0684570.5918900.0122150.123*
C16A0.0413 (7)0.6879 (3)0.0721 (2)0.0953 (15)
H16A0.0959020.7409420.0716610.114*
H16B0.0413660.6995100.0517660.114*
C17A0.0116 (5)0.6606 (2)0.13193 (16)0.0810 (12)
H17A0.0786690.6839580.1576230.097*
H17B0.0761360.6817080.1435460.097*
N1B0.0861 (3)0.55136 (18)0.50023 (12)0.0593 (6)
H1B0.1315900.5788150.5256570.071*
C1B0.1385 (3)0.5041 (2)0.45668 (17)0.0641 (8)
H1BA0.2298590.4976420.4496860.077*
N2B0.1351 (3)0.58594 (16)0.53253 (11)0.0552 (6)
C2B0.0389 (3)0.4672 (2)0.42438 (14)0.0556 (7)
H2B0.0492100.4313710.3927790.067*
N3B0.3094 (2)0.52576 (16)0.47437 (10)0.0498 (5)
C3B0.0838 (3)0.49548 (17)0.44948 (12)0.0455 (6)
N4B0.3115 (3)0.34040 (16)0.31999 (11)0.0512 (5)
C4B0.0494 (3)0.54800 (18)0.49692 (12)0.0505 (6)
N5B0.4312 (2)0.36873 (14)0.34041 (9)0.0438 (5)
C5B0.2619 (3)0.5713 (2)0.51843 (14)0.0551 (7)
H5B0.3260800.5959760.5422340.066*
N6B0.6053 (6)0.4695 (3)0.2061 (2)0.1141 (15)
C6B0.2212 (3)0.48575 (16)0.43928 (11)0.0424 (5)
C7B0.2803 (3)0.43330 (16)0.39393 (11)0.0418 (5)
C8B0.4161 (3)0.42347 (17)0.38433 (12)0.0453 (6)
H8B0.4849070.4501160.4047300.054*
C9B0.2206 (3)0.38016 (19)0.35224 (12)0.0497 (6)
H9B0.1283500.3736120.3477550.060*
C10B0.5602 (3)0.33106 (19)0.32143 (12)0.0499 (6)
H10B0.6303270.3735990.3314800.060*
C11B0.5622 (3)0.3219 (2)0.25717 (12)0.0562 (7)
H11C0.6331460.2812720.2465180.067*
H11D0.4775520.2968520.2447220.067*
C12B0.5835 (4)0.4055 (3)0.22855 (16)0.0690 (9)
C13B0.5960 (4)0.2444 (2)0.35023 (15)0.0651 (9)
H13B0.6796800.2240250.3327280.078*
C14B0.6238 (6)0.2519 (3)0.41325 (19)0.0926 (14)
H14C0.5609090.2919090.4312410.111*
H14D0.7145680.2724950.4201900.111*
C15B0.6050 (10)0.1578 (4)0.4347 (2)0.127 (3)
H15C0.6911290.1326780.4449600.152*
H15D0.5478280.1577920.4679060.152*
C16B0.5441 (9)0.1065 (4)0.3904 (3)0.127 (2)
H16C0.4679160.0737300.4049880.152*
H16D0.6084500.0649700.3749250.152*
H1C0.585 (10)0.601 (6)0.4179 (11)0.190*
H1D0.487 (3)0.577 (6)0.453 (4)0.190*
H2C0.523 (6)0.642 (5)0.336 (4)0.190*
H2D0.649 (8)0.623 (7)0.311 (3)0.190*
H3A0.278 (10)0.424 (3)0.167 (4)0.190*
H3B0.315 (10)0.382 (6)0.1182 (14)0.190*
H4A0.245 (11)0.242 (6)0.2576 (14)0.190*
H4B0.242 (11)0.262 (5)0.193 (2)0.190*
C17B0.4986 (5)0.1708 (3)0.3450 (2)0.0823 (11)
H17C0.5029170.1441570.3077820.099*
H17D0.4076160.1909650.3519830.099*
O20.5916 (3)0.6060 (2)0.33650 (13)0.0809 (7)
O30.2935 (3)0.37210 (17)0.15329 (12)0.0755 (7)
O40.2324 (3)0.22662 (18)0.22250 (11)0.0708 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0533 (11)0.0670 (12)0.0578 (12)0.0018 (10)0.0007 (10)0.0181 (10)
N1A0.0692 (15)0.0509 (12)0.0425 (12)0.0057 (11)0.0025 (11)0.0102 (10)
C1A0.0571 (17)0.0550 (15)0.0544 (16)0.0050 (13)0.0088 (13)0.0021 (12)
N2A0.0598 (14)0.0520 (12)0.0472 (12)0.0052 (11)0.0109 (11)0.0079 (10)
C2A0.0502 (14)0.0461 (13)0.0471 (14)0.0016 (11)0.0017 (11)0.0022 (11)
N3A0.0474 (12)0.0550 (12)0.0450 (12)0.0060 (10)0.0003 (10)0.0013 (10)
C3A0.0471 (13)0.0347 (10)0.0344 (11)0.0009 (9)0.0033 (9)0.0015 (9)
N4A0.0526 (13)0.0519 (12)0.0483 (12)0.0090 (10)0.0025 (10)0.0146 (10)
C4A0.0615 (16)0.0373 (11)0.0354 (12)0.0024 (11)0.0033 (11)0.0006 (10)
N5A0.0495 (12)0.0446 (10)0.0410 (11)0.0017 (9)0.0033 (10)0.0095 (8)
C5A0.0499 (15)0.0598 (16)0.0520 (16)0.0085 (13)0.0085 (13)0.0057 (13)
N6A0.077 (2)0.085 (2)0.086 (2)0.0132 (17)0.0124 (17)0.0258 (18)
C6A0.0456 (13)0.0369 (10)0.0331 (11)0.0004 (9)0.0017 (10)0.0026 (9)
C7A0.0471 (13)0.0386 (11)0.0355 (11)0.0008 (10)0.0016 (10)0.0007 (9)
C8A0.0480 (13)0.0432 (12)0.0409 (13)0.0017 (10)0.0007 (11)0.0064 (10)
C9A0.0444 (13)0.0518 (13)0.0442 (13)0.0034 (11)0.0021 (11)0.0065 (11)
C10A0.0492 (14)0.0482 (13)0.0440 (14)0.0018 (11)0.0052 (11)0.0106 (11)
C11A0.0677 (19)0.0490 (14)0.0564 (17)0.0076 (13)0.0068 (14)0.0092 (12)
C12A0.0570 (17)0.0549 (15)0.069 (2)0.0071 (14)0.0128 (15)0.0014 (14)
C13A0.0605 (17)0.0540 (15)0.0462 (14)0.0039 (13)0.0061 (13)0.0071 (12)
C14A0.085 (2)0.0686 (19)0.0539 (18)0.0127 (17)0.0199 (16)0.0077 (15)
C15A0.144 (5)0.093 (3)0.072 (3)0.021 (3)0.043 (3)0.015 (2)
C16A0.138 (4)0.071 (2)0.077 (3)0.014 (3)0.024 (3)0.0106 (19)
C17A0.123 (4)0.0581 (18)0.062 (2)0.017 (2)0.021 (2)0.0015 (15)
N1B0.0559 (14)0.0574 (13)0.0646 (15)0.0095 (12)0.0218 (12)0.0021 (12)
C1B0.0439 (15)0.0646 (18)0.084 (2)0.0061 (13)0.0107 (15)0.0088 (17)
N2B0.0638 (15)0.0505 (12)0.0513 (13)0.0041 (11)0.0127 (12)0.0059 (11)
C2B0.0477 (14)0.0537 (14)0.0654 (18)0.0017 (12)0.0046 (13)0.0004 (13)
N3B0.0503 (13)0.0503 (12)0.0487 (12)0.0015 (10)0.0072 (10)0.0082 (10)
C3B0.0479 (14)0.0408 (11)0.0478 (14)0.0064 (10)0.0070 (11)0.0033 (10)
N4B0.0515 (13)0.0531 (12)0.0491 (12)0.0027 (10)0.0025 (10)0.0097 (11)
C4B0.0580 (16)0.0438 (13)0.0498 (15)0.0073 (12)0.0166 (13)0.0059 (11)
N5B0.0458 (11)0.0436 (10)0.0419 (11)0.0008 (9)0.0033 (9)0.0063 (8)
C5B0.0605 (17)0.0527 (15)0.0521 (15)0.0033 (13)0.0074 (13)0.0089 (12)
N6B0.127 (4)0.107 (3)0.108 (3)0.004 (3)0.010 (3)0.040 (3)
C6B0.0468 (13)0.0386 (11)0.0419 (12)0.0021 (10)0.0067 (10)0.0011 (10)
C7B0.0457 (13)0.0385 (11)0.0412 (12)0.0015 (10)0.0037 (10)0.0011 (10)
C8B0.0466 (13)0.0434 (12)0.0460 (13)0.0010 (10)0.0033 (11)0.0095 (10)
C9B0.0474 (14)0.0541 (14)0.0477 (14)0.0029 (11)0.0004 (11)0.0055 (12)
C10B0.0504 (15)0.0508 (14)0.0485 (14)0.0076 (12)0.0031 (12)0.0088 (11)
C11B0.0541 (16)0.0665 (17)0.0481 (15)0.0003 (13)0.0099 (13)0.0120 (13)
C12B0.0618 (19)0.084 (2)0.0613 (19)0.0061 (17)0.0055 (16)0.0075 (18)
C13B0.078 (2)0.0549 (16)0.0626 (18)0.0217 (16)0.0004 (16)0.0078 (14)
C14B0.127 (4)0.078 (2)0.073 (3)0.024 (3)0.020 (3)0.003 (2)
C15B0.211 (8)0.089 (3)0.081 (3)0.020 (4)0.019 (4)0.022 (3)
C16B0.158 (6)0.080 (3)0.143 (5)0.005 (4)0.026 (5)0.033 (3)
C17B0.092 (3)0.0642 (19)0.090 (3)0.004 (2)0.011 (2)0.0018 (19)
O20.0754 (17)0.0926 (18)0.0748 (17)0.0053 (15)0.0128 (13)0.0057 (14)
O30.100 (2)0.0619 (13)0.0648 (14)0.0008 (13)0.0096 (14)0.0053 (11)
O40.0682 (15)0.0779 (15)0.0664 (14)0.0123 (12)0.0035 (12)0.0112 (12)
Geometric parameters (Å, º) top
O1—H1C0.868 (14)N1B—C4B1.352 (4)
O1—H1D0.863 (14)C1B—H1BA0.9300
N1A—H1A0.8600C1B—C2B1.371 (5)
N1A—C1A1.373 (4)N2B—C4B1.330 (4)
N1A—C4A1.349 (4)N2B—C5B1.324 (4)
C1A—H1AA0.9300C2B—H2B0.9300
C1A—C2A1.346 (4)C2B—C3B1.424 (4)
N2A—C4A1.337 (4)N3B—C5B1.337 (4)
N2A—C5A1.328 (4)N3B—C6B1.352 (4)
C2A—H2A0.9300C3B—C4B1.418 (4)
C2A—C3A1.427 (4)C3B—C6B1.396 (4)
N3A—C5A1.345 (4)N4B—N5B1.356 (3)
N3A—C6A1.346 (4)N4B—C9B1.328 (4)
C3A—C4A1.414 (4)N5B—C8B1.338 (3)
C3A—C6A1.400 (4)N5B—C10B1.475 (4)
N4A—N5A1.355 (3)C5B—H5B0.9300
N4A—C9A1.331 (4)N6B—C12B1.128 (6)
N5A—C8A1.337 (3)C6B—C7B1.459 (3)
N5A—C10A1.469 (3)C7B—C8B1.379 (4)
C5A—H5A0.9300C7B—C9B1.405 (4)
N6A—C12A1.137 (5)C8B—H8B0.9300
C6A—C7A1.467 (3)C9B—H9B0.9300
C7A—C8A1.371 (4)C10B—H10B0.9800
C7A—C9A1.407 (4)C10B—C11B1.526 (4)
C8A—H8A0.9300C10B—C13B1.522 (4)
C9A—H9A0.9300C11B—H11C0.9700
C10A—H10A0.9800C11B—H11D0.9700
C10A—C11A1.536 (4)C11B—C12B1.453 (5)
C10A—C13A1.519 (4)C13B—H13B0.9800
C11A—H11A0.9700C13B—C14B1.520 (6)
C11A—H11B0.9700C13B—C17B1.484 (6)
C11A—C12A1.464 (5)C14B—H14C0.9700
C13A—H13A0.9800C14B—H14D0.9700
C13A—C14A1.533 (4)C14B—C15B1.525 (7)
C13A—C17A1.534 (4)C15B—H15C0.9700
C14A—H14A0.9700C15B—H15D0.9700
C14A—H14B0.9700C15B—C16B1.439 (9)
C14A—C15A1.502 (6)C16B—H16C0.9700
C15A—H15A0.9700C16B—H16D0.9700
C15A—H15B0.9700C16B—C17B1.519 (7)
C15A—C16A1.503 (7)C17B—H17C0.9700
C16A—H16A0.9700C17B—H17D0.9700
C16A—H16B0.9700O2—H2C0.878 (14)
C16A—C17A1.503 (6)O2—H2D0.872 (14)
C17A—H17A0.9700O3—H3A0.867 (14)
C17A—H17B0.9700O3—H3B0.870 (14)
N1B—H1B0.8600O4—H4A0.872 (14)
N1B—C1B1.358 (5)O4—H4B0.877 (14)
H1C—O1—H1D100 (8)C4B—N1B—H1B125.7
C1A—N1A—H1A126.2C4B—N1B—C1B108.6 (3)
C4A—N1A—H1A126.2N1B—C1B—H1BA124.5
C4A—N1A—C1A107.7 (2)N1B—C1B—C2B111.1 (3)
N1A—C1A—H1AA124.4C2B—C1B—H1BA124.5
C2A—C1A—N1A111.2 (3)C5B—N2B—C4B112.4 (2)
C2A—C1A—H1AA124.4C1B—C2B—H2B127.3
C5A—N2A—C4A112.8 (2)C1B—C2B—C3B105.4 (3)
C1A—C2A—H2A126.9C3B—C2B—H2B127.3
C1A—C2A—C3A106.3 (3)C5B—N3B—C6B118.7 (3)
C3A—C2A—H2A126.9C4B—C3B—C2B106.9 (3)
C5A—N3A—C6A118.4 (3)C6B—C3B—C2B137.4 (3)
C4A—C3A—C2A106.1 (2)C6B—C3B—C4B115.7 (3)
C6A—C3A—C2A137.7 (2)C9B—N4B—N5B104.5 (2)
C6A—C3A—C4A116.2 (2)N1B—C4B—C3B108.0 (3)
C9A—N4A—N5A104.7 (2)N2B—C4B—N1B126.0 (3)
N1A—C4A—C3A108.7 (2)N2B—C4B—C3B126.0 (3)
N2A—C4A—N1A126.0 (2)N4B—N5B—C10B122.3 (2)
N2A—C4A—C3A125.2 (3)C8B—N5B—N4B112.0 (2)
N4A—N5A—C10A120.8 (2)C8B—N5B—C10B125.0 (2)
C8A—N5A—N4A112.0 (2)N2B—C5B—N3B128.3 (3)
C8A—N5A—C10A127.0 (2)N2B—C5B—H5B115.8
N2A—C5A—N3A128.1 (3)N3B—C5B—H5B115.8
N2A—C5A—H5A116.0N3B—C6B—C3B118.9 (2)
N3A—C5A—H5A116.0N3B—C6B—C7B115.7 (2)
N3A—C6A—C3A119.2 (2)C3B—C6B—C7B125.4 (2)
N3A—C6A—C7A118.4 (2)C8B—C7B—C6B125.1 (2)
C3A—C6A—C7A122.4 (2)C8B—C7B—C9B103.7 (2)
C8A—C7A—C6A127.4 (2)C9B—C7B—C6B131.1 (3)
C8A—C7A—C9A104.4 (2)N5B—C8B—C7B107.7 (2)
C9A—C7A—C6A128.2 (2)N5B—C8B—H8B126.1
N5A—C8A—C7A107.6 (2)C7B—C8B—H8B126.1
N5A—C8A—H8A126.2N4B—C9B—C7B112.0 (3)
C7A—C8A—H8A126.2N4B—C9B—H9B124.0
N4A—C9A—C7A111.3 (2)C7B—C9B—H9B124.0
N4A—C9A—H9A124.3N5B—C10B—H10B107.0
C7A—C9A—H9A124.3N5B—C10B—C11B110.5 (2)
N5A—C10A—H10A107.7N5B—C10B—C13B113.7 (3)
N5A—C10A—C11A110.2 (2)C11B—C10B—H10B107.0
N5A—C10A—C13A110.9 (2)C13B—C10B—H10B107.0
C11A—C10A—H10A107.7C13B—C10B—C11B111.3 (2)
C13A—C10A—H10A107.7C10B—C11B—H11C109.0
C13A—C10A—C11A112.3 (2)C10B—C11B—H11D109.0
C10A—C11A—H11A109.2H11C—C11B—H11D107.8
C10A—C11A—H11B109.2C12B—C11B—C10B112.7 (3)
H11A—C11A—H11B107.9C12B—C11B—H11C109.0
C12A—C11A—C10A112.1 (3)C12B—C11B—H11D109.0
C12A—C11A—H11A109.2N6B—C12B—C11B177.2 (5)
C12A—C11A—H11B109.2C10B—C13B—H13B106.4
N6A—C12A—C11A178.5 (4)C14B—C13B—C10B114.7 (3)
C10A—C13A—H13A108.7C14B—C13B—H13B106.4
C10A—C13A—C14A114.2 (3)C17B—C13B—C10B117.3 (3)
C10A—C13A—C17A113.6 (3)C17B—C13B—H13B106.4
C14A—C13A—H13A108.7C17B—C13B—C14B104.9 (4)
C14A—C13A—C17A102.6 (3)C13B—C14B—H14C111.1
C17A—C13A—H13A108.7C13B—C14B—H14D111.1
C13A—C14A—H14A110.8C13B—C14B—C15B103.5 (4)
C13A—C14A—H14B110.8H14C—C14B—H14D109.0
H14A—C14A—H14B108.8C15B—C14B—H14C111.1
C15A—C14A—C13A104.9 (3)C15B—C14B—H14D111.1
C15A—C14A—H14A110.8C14B—C15B—H15C110.0
C15A—C14A—H14B110.8C14B—C15B—H15D110.0
C14A—C15A—H15A110.1H15C—C15B—H15D108.4
C14A—C15A—H15B110.1C16B—C15B—C14B108.4 (4)
C14A—C15A—C16A108.1 (3)C16B—C15B—H15C110.0
H15A—C15A—H15B108.4C16B—C15B—H15D110.0
C16A—C15A—H15A110.1C15B—C16B—H16C110.3
C16A—C15A—H15B110.1C15B—C16B—H16D110.3
C15A—C16A—H16A110.5C15B—C16B—C17B107.0 (4)
C15A—C16A—H16B110.5H16C—C16B—H16D108.6
C15A—C16A—C17A106.3 (4)C17B—C16B—H16C110.3
H16A—C16A—H16B108.7C17B—C16B—H16D110.3
C17A—C16A—H16A110.5C13B—C17B—C16B103.3 (4)
C17A—C16A—H16B110.5C13B—C17B—H17C111.1
C13A—C17A—H17A110.7C13B—C17B—H17D111.1
C13A—C17A—H17B110.7C16B—C17B—H17C111.1
C16A—C17A—C13A105.4 (3)C16B—C17B—H17D111.1
C16A—C17A—H17A110.7H17C—C17B—H17D109.1
C16A—C17A—H17B110.7H2C—O2—H2D109 (8)
H17A—C17A—H17B108.8H3A—O3—H3B104 (8)
C1B—N1B—H1B125.7H4A—O4—H4B125 (8)
N1A—C1A—C2A—C3A0.9 (3)N1B—C1B—C2B—C3B1.2 (4)
C1A—N1A—C4A—N2A178.6 (3)C1B—N1B—C4B—N2B179.5 (3)
C1A—N1A—C4A—C3A0.2 (3)C1B—N1B—C4B—C3B0.6 (3)
C1A—C2A—C3A—C4A1.0 (3)C1B—C2B—C3B—C4B0.7 (3)
C1A—C2A—C3A—C6A176.5 (3)C1B—C2B—C3B—C6B178.4 (3)
C2A—C3A—C4A—N1A0.8 (3)C2B—C3B—C4B—N1B0.1 (3)
C2A—C3A—C4A—N2A179.1 (3)C2B—C3B—C4B—N2B178.8 (3)
C2A—C3A—C6A—N3A175.1 (3)C2B—C3B—C6B—N3B179.2 (3)
C2A—C3A—C6A—C7A4.8 (4)C2B—C3B—C6B—C7B2.4 (5)
N3A—C6A—C7A—C8A160.3 (3)N3B—C6B—C7B—C8B1.1 (4)
N3A—C6A—C7A—C9A18.8 (4)N3B—C6B—C7B—C9B176.4 (3)
C3A—C6A—C7A—C8A19.8 (4)C3B—C6B—C7B—C8B179.5 (3)
C3A—C6A—C7A—C9A161.1 (3)C3B—C6B—C7B—C9B2.0 (4)
N4A—N5A—C8A—C7A0.0 (3)N4B—N5B—C8B—C7B0.5 (3)
N4A—N5A—C10A—C11A56.7 (3)N4B—N5B—C10B—C11B45.1 (4)
N4A—N5A—C10A—C13A68.3 (3)N4B—N5B—C10B—C13B80.9 (3)
C4A—N1A—C1A—C2A0.4 (3)C4B—N1B—C1B—C2B1.2 (4)
C4A—N2A—C5A—N3A1.6 (5)C4B—N2B—C5B—N3B0.6 (5)
C4A—C3A—C6A—N3A2.2 (3)C4B—C3B—C6B—N3B0.1 (4)
C4A—C3A—C6A—C7A177.9 (2)C4B—C3B—C6B—C7B178.5 (2)
N5A—N4A—C9A—C7A0.2 (3)N5B—N4B—C9B—C7B0.7 (3)
N5A—C10A—C11A—C12A58.2 (4)N5B—C10B—C11B—C12B76.3 (3)
N5A—C10A—C13A—C14A175.4 (3)N5B—C10B—C13B—C14B66.1 (5)
N5A—C10A—C13A—C17A58.2 (4)N5B—C10B—C13B—C17B57.5 (4)
C5A—N2A—C4A—N1A175.3 (3)C5B—N2B—C4B—N1B179.9 (3)
C5A—N2A—C4A—C3A2.7 (4)C5B—N2B—C4B—C3B1.5 (4)
C5A—N3A—C6A—C3A3.3 (4)C5B—N3B—C6B—C3B1.7 (4)
C5A—N3A—C6A—C7A176.8 (2)C5B—N3B—C6B—C7B176.8 (3)
C6A—N3A—C5A—N2A1.5 (5)C6B—N3B—C5B—N2B2.3 (5)
C6A—C3A—C4A—N1A177.4 (2)C6B—C3B—C4B—N1B179.3 (2)
C6A—C3A—C4A—N2A1.0 (4)C6B—C3B—C4B—N2B1.9 (4)
C6A—C7A—C8A—N5A179.3 (2)C6B—C7B—C8B—N5B178.1 (2)
C6A—C7A—C9A—N4A179.4 (2)C6B—C7B—C9B—N4B177.5 (3)
C8A—N5A—C10A—C11A128.5 (3)C8B—N5B—C10B—C11B145.3 (3)
C8A—N5A—C10A—C13A106.5 (3)C8B—N5B—C10B—C13B88.7 (3)
C8A—C7A—C9A—N4A0.2 (3)C8B—C7B—C9B—N4B0.5 (3)
C9A—N4A—N5A—C8A0.1 (3)C9B—N4B—N5B—C8B0.7 (3)
C9A—N4A—N5A—C10A175.4 (2)C9B—N4B—N5B—C10B171.6 (3)
C9A—C7A—C8A—N5A0.1 (3)C9B—C7B—C8B—N5B0.0 (3)
C10A—N5A—C8A—C7A175.2 (3)C10B—N5B—C8B—C7B171.0 (2)
C10A—C13A—C14A—C15A156.5 (4)C10B—C13B—C14B—C15B159.8 (5)
C10A—C13A—C17A—C16A158.6 (4)C10B—C13B—C17B—C16B164.8 (4)
C11A—C10A—C13A—C14A60.8 (4)C11B—C10B—C13B—C14B168.3 (4)
C11A—C10A—C13A—C17A178.0 (3)C11B—C10B—C13B—C17B68.1 (4)
C13A—C10A—C11A—C12A177.6 (3)C13B—C10B—C11B—C12B156.3 (3)
C13A—C14A—C15A—C16A19.7 (6)C13B—C14B—C15B—C16B11.3 (8)
C14A—C13A—C17A—C16A34.8 (5)C14B—C13B—C17B—C16B36.4 (5)
C14A—C15A—C16A—C17A2.1 (7)C14B—C15B—C16B—C17B11.0 (9)
C15A—C16A—C17A—C13A23.2 (6)C15B—C16B—C17B—C13B29.5 (8)
C17A—C13A—C14A—C15A33.2 (5)C17B—C13B—C14B—C15B29.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1i0.861.912.771 (3)174
O1—H1C···O20.87 (1)1.93 (2)2.788 (4)171 (10)
O1—H1D···N3B0.86 (1)2.00 (3)2.833 (3)162 (9)
O2—H2C···N3A0.88 (1)2.03 (3)2.879 (4)163 (9)
O2—H2D···O4ii0.87 (1)2.12 (6)2.892 (4)147 (9)
O3—H3A···N4A0.87 (1)2.14 (4)2.957 (3)157 (9)
O3—H3B···N2Biii0.87 (1)2.14 (2)3.011 (4)177 (9)
O4—H4A···N4B0.87 (1)2.20 (5)2.985 (3)150 (9)
O4—H4B···O30.88 (1)1.99 (4)2.813 (4)156 (8)
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+1, y+1/2, z+1/2; (iii) x+1/2, y+1, z1/2.
4-{1-[(1R)-2-Cyano-1-cyclopentylethyl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-3-ium dihydrogen phosphate (rux-p) top
Crystal data top
C17H19N6+·H2PO4Dx = 1.420 Mg m3
Mr = 404.37Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, P212121Cell parameters from 9334 reflections
a = 7.1398 (4) Åθ = 3.3–55.5°
b = 12.0894 (6) ŵ = 1.05 mm1
c = 43.818 (2) ÅT = 296 K
V = 3782.2 (4) Å3Needle, colourless
Z = 80.11 × 0.04 × 0.02 mm
F(000) = 1696
Data collection top
Bruker D8 VENTURE
diffractometer
6947 reflections with I > 2σ(I)
ω and φ scansRint = 0.063
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 60.5°, θmin = 3.3°
Tmin = 0.612, Tmax = 0.752h = 99
84024 measured reflectionsk = 1315
8662 independent reflectionsl = 5656
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0717P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.18 e Å3
8662 reflectionsΔρmin = 0.31 e Å3
559 parametersAbsolute structure: Flack x determined using 2547 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
191 restraintsAbsolute structure parameter: 0.044 (8)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P1A0.65649 (11)0.45547 (6)0.42726 (2)0.04229 (19)
O1A0.6066 (3)0.54089 (16)0.40388 (5)0.0514 (5)
O2A0.5943 (4)0.48670 (18)0.45935 (5)0.0560 (6)
O3A0.5760 (4)0.34235 (18)0.41825 (5)0.0548 (6)
H3AA0.494 (4)0.317 (3)0.4296 (8)0.082*
O4A0.8722 (3)0.4475 (2)0.42736 (7)0.0727 (8)
H4A0.9056360.4026150.4402900.109*
P1B0.21366 (10)0.30897 (6)0.47465 (2)0.03782 (17)
O1B0.3300 (3)0.24909 (15)0.45067 (4)0.0449 (5)
O2B0.2951 (3)0.42237 (17)0.48157 (5)0.0519 (5)
H2BA0.381 (4)0.449 (3)0.4712 (8)0.078*
O3B0.0103 (3)0.31624 (19)0.46592 (5)0.0537 (5)
O4B0.2128 (3)0.2396 (2)0.50465 (5)0.0537 (5)
H4B0.3198550.2196060.5086040.081*
N1A0.8069 (4)1.03408 (19)0.45525 (6)0.0470 (6)
H1A0.8284441.0547360.4737010.056*
C1A0.7998 (5)1.1024 (2)0.43002 (7)0.0514 (7)
H1AA0.8157171.1787250.4304890.062*
N2A0.7629 (4)0.84118 (19)0.46466 (5)0.0467 (6)
C2A0.7663 (5)1.0423 (2)0.40451 (7)0.0472 (7)
H2A0.7560751.0690270.3846690.057*
N3A0.6946 (3)0.73956 (18)0.41971 (5)0.0418 (5)
H3A0.6667530.6758490.4122560.050*
C3A0.7499 (4)0.9295 (2)0.41416 (6)0.0388 (6)
N4A0.5699 (5)0.7373 (2)0.32401 (6)0.0634 (8)
C4A0.7743 (4)0.9295 (2)0.44602 (6)0.0408 (6)
N5A0.6691 (4)0.8315 (2)0.31873 (5)0.0501 (6)
C5A0.7229 (5)0.7489 (2)0.44995 (6)0.0461 (7)
H5A0.7134790.6846350.4615090.055*
N6A0.4936 (9)0.9492 (4)0.21840 (9)0.1197 (19)
C6A0.7086 (4)0.8276 (2)0.40058 (6)0.0380 (6)
C7A0.6785 (4)0.8103 (2)0.36838 (6)0.0413 (6)
C8A0.5788 (5)0.7231 (3)0.35413 (7)0.0566 (9)
H8A0.5263490.6635260.3644820.068*
C9A0.7336 (5)0.8773 (2)0.34439 (6)0.0447 (6)
H9A0.8027010.9423310.3458690.054*
C10A0.6929 (5)0.8715 (3)0.28734 (7)0.0527 (8)
H10C0.7502660.9449810.2886220.063*
C11A0.4956 (6)0.8873 (4)0.27458 (8)0.0668 (10)
H11C0.4280130.8178900.2761490.080*
H11D0.4301060.9415030.2869120.080*
C12A0.4943 (7)0.9235 (4)0.24290 (9)0.0769 (12)
C13A0.8203 (6)0.8007 (3)0.26771 (8)0.0653 (9)
H13A0.8442440.8428370.2490140.078*
C14A0.7510 (7)0.6881 (4)0.25778 (11)0.0862 (13)
H14C0.6710000.6944030.2399720.103*
H14D0.6810590.6527330.2740530.103*
C15A0.9283 (10)0.6222 (5)0.25026 (16)0.123 (2)
H15C0.9218480.5493090.2594300.148*
H15D0.9406920.6136060.2283430.148*
C16A1.0900 (9)0.6840 (6)0.26258 (15)0.121 (2)
H16C1.1651740.7137390.2460720.145*
H16D1.1680810.6356340.2748430.145*
C17A1.0113 (6)0.7771 (4)0.28205 (12)0.0894 (13)
H17C1.0912810.8419340.2811680.107*
H17D0.9981830.7541960.3031500.107*
N1B0.2387 (4)0.2951 (2)0.46540 (7)0.0579 (7)
H1B0.2458860.3336420.4818470.069*
C1B0.1951 (5)0.3349 (3)0.43719 (9)0.0613 (9)
H1BA0.1694410.4086120.4328530.074*
N2B0.3140 (5)0.1196 (2)0.48662 (6)0.0565 (7)
C2B0.1944 (5)0.2521 (3)0.41632 (8)0.0538 (8)
H2B0.1666160.2584220.3956580.065*
N3B0.3096 (4)0.02370 (18)0.45001 (5)0.0437 (6)
H3B0.3235060.0934950.4469770.052*
C3B0.2446 (4)0.1535 (2)0.43224 (7)0.0436 (6)
N4B0.2251 (6)0.0366 (3)0.34516 (6)0.0733 (9)
C4B0.2688 (4)0.1855 (2)0.46329 (7)0.0466 (7)
N5B0.2470 (5)0.1350 (2)0.35969 (6)0.0584 (7)
C5B0.3305 (6)0.0154 (3)0.47894 (7)0.0550 (8)
H5B0.3583360.0352040.4942610.066*
N6B0.6761 (8)0.1284 (4)0.31372 (12)0.1215 (18)
C6B0.2678 (4)0.0417 (2)0.42557 (6)0.0400 (6)
C7B0.2549 (4)0.0101 (2)0.39595 (6)0.0417 (6)
C8B0.2285 (6)0.0375 (3)0.36689 (8)0.0632 (9)
H8B0.2151230.1130320.3635520.076*
C9B0.2651 (5)0.1216 (3)0.38945 (7)0.0516 (8)
H9B0.2817960.1778800.4036520.062*
C10B0.2655 (7)0.2388 (4)0.34224 (9)0.0811 (13)
H10A0.2428710.2142190.3212510.097*0.388 (6)
H10B0.2161550.2295270.3215300.097*0.612 (6)
C11B0.4702 (8)0.2727 (3)0.34127 (10)0.0904 (16)
H11A0.4810010.3432200.3308750.109*
H11B0.5154370.2823910.3619710.109*
C12B0.5875 (8)0.1917 (4)0.32576 (10)0.0865 (14)
C13B0.1702 (13)0.3396 (5)0.35836 (18)0.0632 (19)0.612 (6)
H13B0.2048850.3402110.3799960.076*0.612 (6)
C14B0.2067 (12)0.4547 (5)0.34448 (19)0.084 (2)0.612 (6)
H14A0.3083440.4919480.3549780.101*0.612 (6)
H14B0.2370820.4491260.3229610.101*0.612 (6)
C15B0.0201 (19)0.5161 (9)0.3493 (3)0.103 (4)0.612 (6)
H15A0.0094380.5435450.3699860.124*0.612 (6)
H15B0.0080350.5775970.3351720.124*0.612 (6)
C16B0.1270 (15)0.4270 (9)0.3428 (3)0.105 (3)0.612 (6)
H16A0.2440980.4443240.3529220.126*0.612 (6)
H16B0.1498080.4205020.3210280.126*0.612 (6)
C17B0.0436 (12)0.3207 (6)0.35536 (18)0.082 (2)0.612 (6)
H17A0.0687290.2595430.3416420.098*0.612 (6)
H17B0.0976030.3037470.3751270.098*0.612 (6)
C180.091 (2)0.3083 (10)0.3490 (3)0.066 (3)0.388 (6)
H180.0110640.2610660.3564440.079*0.388 (6)
C190.1496 (19)0.3913 (11)0.3738 (3)0.088 (3)0.388 (6)
H19A0.2842350.3896650.3767460.105*0.388 (6)
H19B0.0892600.3738780.3930550.105*0.388 (6)
C200.086 (3)0.5074 (13)0.3621 (4)0.104 (5)0.388 (6)
H20A0.0246120.5486280.3782970.124*0.388 (6)
H20B0.1922260.5497280.3548360.124*0.388 (6)
C210.051 (3)0.4833 (14)0.3361 (4)0.099 (4)0.388 (6)
H21A0.1767170.4723740.3438640.119*0.388 (6)
H21B0.0520040.5433800.3214600.119*0.388 (6)
C220.0237 (19)0.3790 (8)0.3220 (2)0.076 (3)0.388 (6)
H22A0.1266880.3952550.3082520.092*0.388 (6)
H22B0.0737820.3410450.3106610.092*0.388 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P1A0.0481 (4)0.0328 (3)0.0460 (4)0.0038 (3)0.0006 (3)0.0085 (3)
O1A0.0720 (15)0.0337 (10)0.0485 (12)0.0026 (10)0.0117 (10)0.0076 (9)
O2A0.0746 (16)0.0481 (12)0.0454 (12)0.0180 (11)0.0004 (11)0.0007 (10)
O3A0.0704 (15)0.0380 (11)0.0561 (14)0.0073 (10)0.0154 (11)0.0008 (9)
O4A0.0480 (14)0.0832 (19)0.0869 (19)0.0059 (12)0.0004 (13)0.0444 (15)
P1B0.0406 (3)0.0363 (3)0.0366 (3)0.0006 (3)0.0005 (3)0.0031 (3)
O1B0.0562 (12)0.0322 (9)0.0464 (11)0.0047 (9)0.0093 (9)0.0043 (8)
O2B0.0611 (14)0.0418 (11)0.0527 (12)0.0064 (10)0.0132 (11)0.0088 (9)
O3B0.0424 (11)0.0631 (13)0.0557 (12)0.0005 (10)0.0036 (9)0.0195 (11)
O4B0.0473 (11)0.0662 (14)0.0475 (11)0.0044 (11)0.0017 (10)0.0194 (10)
N1A0.0613 (16)0.0367 (12)0.0432 (13)0.0005 (12)0.0049 (12)0.0071 (10)
C1A0.066 (2)0.0307 (13)0.0573 (18)0.0013 (14)0.0017 (16)0.0025 (12)
N2A0.0620 (16)0.0399 (12)0.0381 (12)0.0007 (11)0.0038 (12)0.0025 (10)
C2A0.0613 (19)0.0352 (14)0.0453 (15)0.0039 (14)0.0004 (14)0.0048 (12)
N3A0.0545 (14)0.0291 (10)0.0418 (12)0.0008 (11)0.0041 (11)0.0003 (9)
C3A0.0430 (15)0.0329 (13)0.0405 (13)0.0013 (11)0.0004 (12)0.0005 (10)
N4A0.092 (2)0.0513 (16)0.0467 (15)0.0218 (16)0.0096 (15)0.0009 (13)
C4A0.0428 (15)0.0357 (13)0.0439 (15)0.0020 (12)0.0038 (12)0.0013 (11)
N5A0.0674 (17)0.0466 (13)0.0362 (12)0.0092 (13)0.0048 (12)0.0033 (10)
C5A0.0622 (18)0.0363 (14)0.0399 (14)0.0003 (14)0.0042 (14)0.0051 (11)
N6A0.181 (5)0.123 (4)0.055 (2)0.069 (4)0.015 (3)0.005 (2)
C6A0.0411 (14)0.0341 (13)0.0387 (13)0.0018 (12)0.0001 (11)0.0030 (10)
C7A0.0504 (16)0.0340 (13)0.0394 (14)0.0013 (13)0.0040 (12)0.0000 (11)
C8A0.080 (2)0.0428 (17)0.0464 (18)0.0162 (16)0.0062 (16)0.0025 (13)
C9A0.0552 (17)0.0379 (14)0.0410 (14)0.0053 (13)0.0010 (13)0.0001 (11)
C10A0.070 (2)0.0509 (17)0.0374 (15)0.0004 (16)0.0015 (15)0.0019 (13)
C11A0.075 (3)0.079 (3)0.0462 (19)0.010 (2)0.0043 (18)0.0017 (18)
C12A0.098 (3)0.082 (3)0.050 (2)0.028 (2)0.012 (2)0.0024 (19)
C13A0.077 (2)0.067 (2)0.0519 (18)0.003 (2)0.0066 (17)0.0026 (17)
C14A0.101 (3)0.076 (3)0.082 (3)0.004 (3)0.004 (3)0.024 (2)
C15A0.127 (5)0.094 (4)0.149 (6)0.020 (4)0.013 (4)0.041 (4)
C16A0.099 (4)0.130 (5)0.133 (5)0.029 (4)0.016 (4)0.028 (4)
C17A0.066 (3)0.093 (3)0.109 (3)0.006 (2)0.000 (2)0.016 (3)
N1B0.0722 (18)0.0368 (12)0.0646 (16)0.0004 (13)0.0084 (15)0.0106 (12)
C1B0.068 (2)0.0318 (15)0.084 (2)0.0075 (15)0.0019 (19)0.0005 (15)
N2B0.086 (2)0.0404 (13)0.0429 (14)0.0048 (14)0.0076 (14)0.0057 (11)
C2B0.0595 (19)0.0401 (15)0.0617 (19)0.0045 (15)0.0040 (16)0.0043 (14)
N3B0.0611 (15)0.0312 (11)0.0388 (12)0.0019 (11)0.0045 (11)0.0029 (9)
C3B0.0428 (15)0.0358 (14)0.0523 (16)0.0006 (11)0.0054 (13)0.0004 (11)
N4B0.109 (3)0.0680 (18)0.0426 (14)0.012 (2)0.0125 (17)0.0003 (13)
C4B0.0529 (16)0.0344 (14)0.0527 (16)0.0023 (13)0.0096 (14)0.0063 (12)
N5B0.085 (2)0.0533 (15)0.0370 (13)0.0080 (15)0.0016 (14)0.0033 (11)
C5B0.084 (2)0.0430 (16)0.0378 (15)0.0037 (16)0.0025 (16)0.0006 (12)
N6B0.142 (4)0.074 (3)0.148 (4)0.014 (3)0.061 (4)0.002 (3)
C6B0.0389 (13)0.0396 (14)0.0414 (13)0.0014 (12)0.0045 (12)0.0004 (11)
C7B0.0427 (15)0.0424 (15)0.0400 (14)0.0009 (12)0.0009 (12)0.0000 (11)
C8B0.089 (3)0.0479 (17)0.0524 (18)0.0012 (19)0.0078 (19)0.0030 (14)
C9B0.071 (2)0.0471 (16)0.0368 (14)0.0010 (16)0.0007 (15)0.0037 (12)
C10B0.119 (4)0.072 (2)0.0523 (19)0.037 (3)0.025 (2)0.0273 (17)
C11B0.146 (5)0.050 (2)0.075 (3)0.016 (2)0.048 (3)0.0171 (19)
C12B0.119 (4)0.059 (2)0.082 (3)0.010 (3)0.037 (3)0.014 (2)
C13B0.097 (5)0.041 (3)0.051 (4)0.006 (3)0.007 (4)0.003 (3)
C14B0.105 (5)0.050 (3)0.097 (5)0.012 (4)0.017 (4)0.015 (3)
C15B0.128 (10)0.069 (6)0.114 (9)0.029 (6)0.004 (7)0.026 (6)
C16B0.105 (6)0.096 (6)0.115 (7)0.034 (5)0.006 (5)0.019 (5)
C17B0.092 (5)0.065 (4)0.088 (5)0.007 (4)0.010 (4)0.000 (4)
C180.075 (7)0.065 (6)0.058 (6)0.011 (6)0.001 (5)0.015 (5)
C190.084 (7)0.100 (8)0.080 (7)0.032 (6)0.005 (6)0.011 (6)
C200.120 (10)0.078 (8)0.113 (10)0.005 (8)0.002 (8)0.000 (8)
C210.122 (11)0.063 (8)0.113 (10)0.013 (7)0.012 (8)0.011 (7)
C220.103 (7)0.068 (6)0.058 (5)0.010 (5)0.018 (5)0.016 (5)
Geometric parameters (Å, º) top
P1A—O1A1.498 (2)N1B—C4B1.345 (4)
P1A—O2A1.522 (2)C1B—H1BA0.9300
P1A—O3A1.535 (2)C1B—C2B1.355 (5)
P1A—O4A1.543 (2)N2B—C4B1.336 (4)
O3A—H3AA0.825 (14)N2B—C5B1.309 (4)
O4A—H4A0.8200C2B—H2B0.9300
P1B—O1B1.523 (2)C2B—C3B1.427 (4)
P1B—O2B1.520 (2)N3B—H3B0.8600
P1B—O3B1.504 (2)N3B—C5B1.361 (4)
P1B—O4B1.559 (2)N3B—C6B1.364 (3)
O2B—H2BA0.829 (14)C3B—C4B1.425 (4)
O4B—H4B0.8200C3B—C6B1.393 (4)
N1A—H1A0.8600N4B—N5B1.358 (4)
N1A—C1A1.381 (4)N4B—C8B1.308 (5)
N1A—C4A1.348 (3)N5B—C9B1.320 (4)
C1A—H1AA0.9300N5B—C10B1.475 (4)
C1A—C2A1.354 (4)C5B—H5B0.9300
N2A—C4A1.347 (3)N6B—C12B1.124 (6)
N2A—C5A1.320 (4)C6B—C7B1.444 (4)
C2A—H2A0.9300C7B—C8B1.410 (4)
C2A—C3A1.434 (4)C7B—C9B1.380 (4)
N3A—H3A0.8600C8B—H8B0.9300
N3A—C5A1.345 (4)C9B—H9B0.9300
N3A—C6A1.358 (3)C10B—H10A0.9800
C3A—C4A1.407 (4)C10B—H10B0.9800
C3A—C6A1.399 (4)C10B—C11B1.519 (8)
N4A—N5A1.360 (4)C10B—C13B1.564 (8)
N4A—C8A1.333 (4)C10B—C181.533 (12)
N5A—C9A1.336 (4)C11B—H11A0.9700
N5A—C10A1.468 (4)C11B—H11B0.9700
C5A—H5A0.9300C11B—C12B1.457 (6)
N6A—C12A1.118 (5)C13B—H13B0.9800
C6A—C7A1.443 (4)C13B—C14B1.540 (9)
C7A—C8A1.417 (4)C13B—C17B1.549 (11)
C7A—C9A1.384 (4)C14B—H14A0.9700
C8A—H8A0.9300C14B—H14B0.9700
C9A—H9A0.9300C14B—C15B1.539 (14)
C10A—H10C0.9800C15B—H15A0.9700
C10A—C11A1.527 (5)C15B—H15B0.9700
C10A—C13A1.517 (5)C15B—C16B1.531 (15)
C11A—H11C0.9700C16B—H16A0.9700
C11A—H11D0.9700C16B—H16B0.9700
C11A—C12A1.455 (5)C16B—C17B1.519 (11)
C13A—H13A0.9800C17B—H17A0.9700
C13A—C14A1.511 (6)C17B—H17B0.9700
C13A—C17A1.528 (6)C18—H180.9800
C14A—H14C0.9700C18—C191.538 (15)
C14A—H14D0.9700C18—C221.538 (13)
C14A—C15A1.531 (7)C19—H19A0.9700
C15A—H15C0.9700C19—H19B0.9700
C15A—H15D0.9700C19—C201.561 (18)
C15A—C16A1.477 (9)C20—H20A0.9700
C16A—H16C0.9700C20—H20B0.9700
C16A—H16D0.9700C20—C211.528 (18)
C16A—C17A1.521 (7)C21—H21A0.9700
C17A—H17C0.9700C21—H21B0.9700
C17A—H17D0.9700C21—C221.503 (17)
N1B—H1B0.8600C22—H22A0.9700
N1B—C1B1.362 (4)C22—H22B0.9700
O1A—P1A—O2A113.05 (13)C5B—N3B—H3B118.2
O1A—P1A—O3A110.42 (13)C5B—N3B—C6B123.6 (2)
O1A—P1A—O4A106.40 (14)C6B—N3B—H3B118.2
O2A—P1A—O3A110.45 (13)C4B—C3B—C2B105.7 (3)
O2A—P1A—O4A107.69 (16)C6B—C3B—C2B137.6 (3)
O3A—P1A—O4A108.61 (17)C6B—C3B—C4B116.7 (3)
P1A—O3A—H3AA116 (3)C8B—N4B—N5B104.9 (3)
P1A—O4A—H4A109.5N1B—C4B—C3B108.3 (3)
O1B—P1B—O4B109.16 (13)N2B—C4B—N1B125.0 (3)
O2B—P1B—O1B110.98 (12)N2B—C4B—C3B126.7 (3)
O2B—P1B—O4B108.57 (13)N4B—N5B—C10B120.8 (3)
O3B—P1B—O1B112.26 (13)C9B—N5B—N4B111.5 (3)
O3B—P1B—O2B111.55 (14)C9B—N5B—C10B127.4 (3)
O3B—P1B—O4B104.02 (12)N2B—C5B—N3B124.3 (3)
P1B—O2B—H2BA122 (3)N2B—C5B—H5B117.8
P1B—O4B—H4B109.5N3B—C5B—H5B117.8
C1A—N1A—H1A125.8N3B—C6B—C3B115.1 (2)
C4A—N1A—H1A125.8N3B—C6B—C7B117.9 (2)
C4A—N1A—C1A108.3 (2)C3B—C6B—C7B127.0 (3)
N1A—C1A—H1AA124.9C8B—C7B—C6B130.0 (3)
C2A—C1A—N1A110.3 (3)C9B—C7B—C6B127.3 (3)
C2A—C1A—H1AA124.9C9B—C7B—C8B102.7 (3)
C5A—N2A—C4A112.7 (2)N4B—C8B—C7B112.4 (3)
C1A—C2A—H2A126.8N4B—C8B—H8B123.8
C1A—C2A—C3A106.3 (3)C7B—C8B—H8B123.8
C3A—C2A—H2A126.8N5B—C9B—C7B108.6 (3)
C5A—N3A—H3A119.0N5B—C9B—H9B125.7
C5A—N3A—C6A122.1 (2)C7B—C9B—H9B125.7
C6A—N3A—H3A119.0N5B—C10B—H10A102.4
C4A—C3A—C2A106.4 (2)N5B—C10B—H10B110.5
C6A—C3A—C2A136.9 (3)N5B—C10B—C11B109.3 (3)
C6A—C3A—C4A116.6 (2)N5B—C10B—C13B113.0 (4)
C8A—N4A—N5A104.6 (3)N5B—C10B—C18107.0 (6)
N1A—C4A—C3A108.6 (2)C11B—C10B—H10A102.4
N2A—C4A—N1A124.9 (3)C11B—C10B—H10B110.5
N2A—C4A—C3A126.5 (2)C11B—C10B—C13B102.8 (5)
N4A—N5A—C10A119.7 (2)C11B—C10B—C18129.9 (7)
C9A—N5A—N4A112.6 (2)C13B—C10B—H10B110.5
C9A—N5A—C10A127.7 (3)C18—C10B—H10A102.4
N2A—C5A—N3A125.8 (3)C10B—C11B—H11A109.1
N2A—C5A—H5A117.1C10B—C11B—H11B109.1
N3A—C5A—H5A117.1H11A—C11B—H11B107.8
N3A—C6A—C3A116.3 (2)C12B—C11B—C10B112.6 (4)
N3A—C6A—C7A118.6 (2)C12B—C11B—H11A109.1
C3A—C6A—C7A125.1 (2)C12B—C11B—H11B109.1
C8A—C7A—C6A127.8 (3)N6B—C12B—C11B179.2 (7)
C9A—C7A—C6A128.0 (3)C10B—C13B—H13B109.4
C9A—C7A—C8A104.1 (2)C14B—C13B—C10B116.9 (6)
N4A—C8A—C7A111.4 (3)C14B—C13B—H13B109.4
N4A—C8A—H8A124.3C14B—C13B—C17B105.5 (6)
C7A—C8A—H8A124.3C17B—C13B—C10B106.0 (7)
N5A—C9A—C7A107.3 (3)C17B—C13B—H13B109.4
N5A—C9A—H9A126.3C13B—C14B—H14A111.0
C7A—C9A—H9A126.3C13B—C14B—H14B111.0
N5A—C10A—H10C107.1H14A—C14B—H14B109.0
N5A—C10A—C11A106.1 (3)C15B—C14B—C13B103.6 (7)
N5A—C10A—C13A114.5 (3)C15B—C14B—H14A111.0
C11A—C10A—H10C107.1C15B—C14B—H14B111.0
C13A—C10A—H10C107.1C14B—C15B—H15A111.1
C13A—C10A—C11A114.6 (3)C14B—C15B—H15B111.1
C10A—C11A—H11C109.0H15A—C15B—H15B109.1
C10A—C11A—H11D109.0C16B—C15B—C14B103.2 (8)
H11C—C11A—H11D107.8C16B—C15B—H15A111.1
C12A—C11A—C10A113.1 (3)C16B—C15B—H15B111.1
C12A—C11A—H11C109.0C15B—C16B—H16A110.7
C12A—C11A—H11D109.0C15B—C16B—H16B110.7
N6A—C12A—C11A178.6 (5)H16A—C16B—H16B108.8
C10A—C13A—H13A106.5C17B—C16B—C15B105.0 (8)
C10A—C13A—C17A114.0 (3)C17B—C16B—H16A110.7
C14A—C13A—C10A118.4 (4)C17B—C16B—H16B110.7
C14A—C13A—H13A106.5C13B—C17B—H17A110.3
C14A—C13A—C17A104.1 (4)C13B—C17B—H17B110.3
C17A—C13A—H13A106.5C16B—C17B—C13B107.0 (7)
C13A—C14A—H14C110.7C16B—C17B—H17A110.3
C13A—C14A—H14D110.7C16B—C17B—H17B110.3
C13A—C14A—C15A105.0 (4)H17A—C17B—H17B108.6
H14C—C14A—H14D108.8C10B—C18—H18110.4
C15A—C14A—H14C110.7C10B—C18—C19105.8 (10)
C15A—C14A—H14D110.7C10B—C18—C22114.1 (9)
C14A—C15A—H15C110.2C19—C18—H18110.4
C14A—C15A—H15D110.2C22—C18—H18110.4
H15C—C15A—H15D108.5C22—C18—C19105.5 (9)
C16A—C15A—C14A107.7 (4)C18—C19—H19A110.5
C16A—C15A—H15C110.2C18—C19—H19B110.5
C16A—C15A—H15D110.2C18—C19—C20106.0 (10)
C15A—C16A—H16C110.3H19A—C19—H19B108.7
C15A—C16A—H16D110.3C20—C19—H19A110.5
C15A—C16A—C17A106.9 (5)C20—C19—H19B110.5
H16C—C16A—H16D108.6C19—C20—H20A110.7
C17A—C16A—H16C110.3C19—C20—H20B110.7
C17A—C16A—H16D110.3H20A—C20—H20B108.8
C13A—C17A—H17C111.0C21—C20—C19105.0 (12)
C13A—C17A—H17D111.0C21—C20—H20A110.7
C16A—C17A—C13A103.7 (4)C21—C20—H20B110.7
C16A—C17A—H17C111.0C20—C21—H21A111.0
C16A—C17A—H17D111.0C20—C21—H21B111.0
H17C—C17A—H17D109.0H21A—C21—H21B109.0
C1B—N1B—H1B125.6C22—C21—C20104.0 (12)
C4B—N1B—H1B125.6C22—C21—H21A111.0
C4B—N1B—C1B108.8 (3)C22—C21—H21B111.0
N1B—C1B—H1BA124.7C18—C22—H22A110.8
C2B—C1B—N1B110.6 (3)C18—C22—H22B110.8
C2B—C1B—H1BA124.7C21—C22—C18105.0 (10)
C5B—N2B—C4B113.5 (3)C21—C22—H22A110.8
C1B—C2B—H2B126.7C21—C22—H22B110.8
C1B—C2B—C3B106.6 (3)H22A—C22—H22B108.8
C3B—C2B—H2B126.7
N1A—C1A—C2A—C3A0.4 (4)C2B—C3B—C6B—N3B176.7 (3)
C1A—N1A—C4A—N2A177.1 (3)C2B—C3B—C6B—C7B4.3 (6)
C1A—N1A—C4A—C3A1.4 (4)N3B—C6B—C7B—C8B174.6 (3)
C1A—C2A—C3A—C4A0.4 (4)N3B—C6B—C7B—C9B5.8 (5)
C1A—C2A—C3A—C6A176.4 (3)C3B—C6B—C7B—C8B4.4 (5)
C2A—C3A—C4A—N1A1.1 (3)C3B—C6B—C7B—C9B175.2 (3)
C2A—C3A—C4A—N2A177.4 (3)N4B—N5B—C9B—C7B0.1 (4)
C2A—C3A—C6A—N3A175.1 (3)N4B—N5B—C10B—C11B101.8 (4)
C2A—C3A—C6A—C7A4.2 (6)N4B—N5B—C10B—C13B144.5 (5)
N3A—C6A—C7A—C8A22.2 (5)N4B—N5B—C10B—C18113.4 (6)
N3A—C6A—C7A—C9A160.8 (3)C4B—N1B—C1B—C2B0.5 (4)
C3A—C6A—C7A—C8A157.2 (3)C4B—N2B—C5B—N3B1.8 (5)
C3A—C6A—C7A—C9A19.9 (5)C4B—C3B—C6B—N3B0.6 (4)
N4A—N5A—C9A—C7A1.0 (4)C4B—C3B—C6B—C7B178.5 (3)
N4A—N5A—C10A—C11A57.3 (4)N5B—N4B—C8B—C7B0.7 (5)
N4A—N5A—C10A—C13A70.1 (4)N5B—C10B—C11B—C12B62.2 (5)
C4A—N1A—C1A—C2A1.1 (4)N5B—C10B—C13B—C14B171.1 (6)
C4A—N2A—C5A—N3A0.3 (5)N5B—C10B—C13B—C17B71.8 (6)
C4A—C3A—C6A—N3A0.6 (4)N5B—C10B—C18—C1998.4 (9)
C4A—C3A—C6A—C7A180.0 (3)N5B—C10B—C18—C22146.1 (9)
N5A—N4A—C8A—C7A2.0 (4)C5B—N2B—C4B—N1B178.1 (3)
N5A—C10A—C11A—C12A178.0 (3)C5B—N2B—C4B—C3B2.1 (5)
N5A—C10A—C13A—C14A70.9 (4)C5B—N3B—C6B—C3B0.9 (4)
N5A—C10A—C13A—C17A52.0 (5)C5B—N3B—C6B—C7B178.2 (3)
C5A—N2A—C4A—N1A177.6 (3)C6B—N3B—C5B—N2B0.3 (5)
C5A—N2A—C4A—C3A0.6 (4)C6B—C3B—C4B—N1B179.2 (3)
C5A—N3A—C6A—C3A1.4 (4)C6B—C3B—C4B—N2B1.0 (5)
C5A—N3A—C6A—C7A179.2 (3)C6B—C7B—C8B—N4B179.7 (3)
C6A—N3A—C5A—N2A1.3 (5)C6B—C7B—C9B—N5B180.0 (3)
C6A—C3A—C4A—N1A178.1 (3)C8B—N4B—N5B—C9B0.5 (5)
C6A—C3A—C4A—N2A0.4 (5)C8B—N4B—N5B—C10B175.1 (4)
C6A—C7A—C8A—N4A176.2 (3)C8B—C7B—C9B—N5B0.3 (4)
C6A—C7A—C9A—N5A177.4 (3)C9B—N5B—C10B—C11B71.9 (5)
C8A—N4A—N5A—C9A1.9 (4)C9B—N5B—C10B—C13B41.9 (7)
C8A—N4A—N5A—C10A178.6 (3)C9B—N5B—C10B—C1872.9 (8)
C8A—C7A—C9A—N5A0.2 (4)C9B—C7B—C8B—N4B0.6 (4)
C9A—N5A—C10A—C11A122.2 (4)C10B—N5B—C9B—C7B174.3 (4)
C9A—N5A—C10A—C13A110.4 (4)C10B—C13B—C14B—C15B144.7 (9)
C9A—C7A—C8A—N4A1.4 (4)C10B—C13B—C17B—C16B129.5 (6)
C10A—N5A—C9A—C7A179.5 (3)C10B—C18—C19—C20129.7 (12)
C10A—C13A—C14A—C15A158.0 (4)C10B—C18—C22—C21145.0 (13)
C10A—C13A—C17A—C16A166.1 (4)C11B—C10B—C13B—C14B53.5 (8)
C11A—C10A—C13A—C14A52.0 (5)C11B—C10B—C13B—C17B170.6 (5)
C11A—C10A—C13A—C17A174.9 (4)C11B—C10B—C18—C1936.5 (11)
C13A—C10A—C11A—C12A50.7 (5)C11B—C10B—C18—C2279.0 (12)
C13A—C14A—C15A—C16A13.4 (7)C13B—C10B—C11B—C12B177.6 (4)
C14A—C13A—C17A—C16A35.7 (5)C13B—C14B—C15B—C16B39.3 (11)
C14A—C15A—C16A—C17A9.1 (7)C14B—C13B—C17B—C16B5.0 (9)
C15A—C16A—C17A—C13A27.7 (6)C14B—C15B—C16B—C17B36.4 (11)
C17A—C13A—C14A—C15A30.3 (5)C15B—C16B—C17B—C13B19.5 (11)
N1B—C1B—C2B—C3B1.2 (4)C17B—C13B—C14B—C15B27.2 (10)
C1B—N1B—C4B—N2B179.8 (3)C18—C10B—C11B—C12B163.6 (7)
C1B—N1B—C4B—C3B0.4 (4)C18—C19—C20—C2114.9 (19)
C1B—C2B—C3B—C4B1.4 (4)C19—C18—C22—C2129.3 (15)
C1B—C2B—C3B—C6B178.9 (4)C19—C20—C21—C2233 (2)
C2B—C3B—C4B—N1B1.1 (4)C20—C21—C22—C1838.8 (19)
C2B—C3B—C4B—N2B179.1 (3)C22—C18—C19—C208.5 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3AA···O1B0.83 (1)1.70 (2)2.525 (3)173 (4)
O4A—H4A···O3Bi0.821.712.519 (3)171
O2B—H2BA···O2A0.83 (1)1.67 (2)2.473 (3)162 (4)
O4B—H4B···O3Bii0.821.812.575 (3)154
N1A—H1A···O2Biii0.861.992.819 (3)161
N3A—H3A···O1A0.861.732.578 (3)170
N1B—H1B···N2Aiv0.862.353.120 (4)149
N3B—H3B···O1B0.861.892.729 (3)165
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z+1; (iii) x+1/2, y+3/2, z+1; (iv) x1/2, y+1/2, z+1.
Selected torsion angles (°) of the linker of the chiral stereocentre of ruxolitinib top
RUX (molecule A/B/C/D)RUX-2H (molecule A/B)RUX-P (molecule A/B)
N5—C10—C11—C1248.1 (4)/53.0 (4)/47.8 (4)/52.5 (4)58.2 (4)/76.3 (3)-178.0 (3)/62.2 (5)
C13—C10—C11—C12172.0 (3)/178.7 (3)/174.5 (3)/175.5 (3)-177.6 (3)/-156.3 (3)-50.7 (5)/-177.6 (4)
Selected interplanar angles (°) between the pyrrolo[2,3-d]pyrimidine and pyrazole rings top
RUX (molecule A/B/C/D)RUX-2H (molecule A/B)RUX-P (molecule A/B)
Interplanar18.86/20.99/18.33/83.7721.35/4.1122.94/6.35
The percentage contributions (%) of the intermolecular interactions to the total Hirshfeld surface top
C···HN···HH···CH···NH···H
RUX A12.020.38.916.241.0
RUX B12.318.58.613.545.1
RUX C12.117.111.214.042.2
RUX D12.316.910.815.141.4
The percentage contributions (%) of the intermolecular interactions to the total Hirshfeld surface top
C···HN···HO···HH···CH···NH···OH···H
RUX-2H A7.318.00.06.08.54.648.2
RUX-2H B9.017.80.05.111.63.046.9
RUX-P A5.912.00.04.413.18.745.3
RUX-P B5.115.30.04.48.212.942.9
 

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