Comparison of the crystal structures of the JAK1/2 inhibitor ruxolitinib and its hydrate and phos­phate

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.

Computing details

(3R)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (rux)

Crystal data

C17H18N6	F(000) = 1296
Mr = 306.37	Dx = 1.260 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 8.7110 (2) Å	Cell parameters from 9807 reflections
b = 19.5857 (4) Å	θ = 3.3–68.2°
c = 18.9372 (4) Å	µ = 0.64 mm^−1
β = 90.857 (1)°	T = 296 K
V = 3230.53 (12) Å^3	Needle, colourless
Z = 8	0.42 × 0.12 × 0.1 mm

Data collection

Bruker D8 VENTURE diffractometer	10907 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.035
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 68.4°, θmin = 2.3°
Tmin = 0.642, Tmax = 0.753	h = −10→10
44067 measured reflections	k = −23→23
11668 independent reflections	l = −22→22

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0775P)^2 + 0.3655P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.46 e Å^−3
11668 reflections	Δρmin = −0.26 e Å^−3
829 parameters	Absolute structure: Flack x determined using 4803 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.01 (11)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.0235 (3)	0.34297 (14)	0.98134 (17)	0.0608 (7)
H1A	0.000323	0.300724	0.987495	0.073*
C1A	0.0811 (4)	0.37074 (17)	0.9208 (2)	0.0609 (8)
H1AA	0.102538	0.346249	0.880021	0.073*
N2A	−0.0466 (4)	0.38666 (15)	1.09420 (17)	0.0658 (7)
C2A	0.1026 (4)	0.43904 (16)	0.92864 (18)	0.0552 (7)
H2A	0.139320	0.469168	0.894902	0.066*
N3A	−0.0103 (3)	0.50807 (15)	1.10703 (16)	0.0624 (7)
C3A	0.0579 (3)	0.45546 (14)	0.99861 (16)	0.0466 (6)
N4A	0.0578 (3)	0.69787 (13)	1.00863 (15)	0.0539 (6)
C4A	0.0093 (3)	0.39350 (16)	1.02998 (18)	0.0528 (7)
N5A	0.1398 (3)	0.67321 (12)	0.95401 (13)	0.0478 (5)
C5A	−0.0517 (5)	0.4460 (2)	1.1289 (2)	0.0699 (9)
H5A	−0.089346	0.443793	1.174538	0.084*
N6A	−0.1127 (6)	0.6824 (3)	0.8057 (4)	0.145 (2)
C6A	0.0430 (3)	0.51378 (16)	1.04035 (17)	0.0492 (6)
C7A	0.0740 (3)	0.58304 (15)	1.01573 (16)	0.0476 (6)
C8A	0.0182 (4)	0.64369 (16)	1.04579 (18)	0.0554 (7)
H8A	−0.039387	0.645440	1.086708	0.067*
C9A	0.1508 (3)	0.60461 (15)	0.95691 (17)	0.0505 (6)
H9A	0.201244	0.576864	0.924866	0.061*
C10A	0.2154 (4)	0.72084 (14)	0.90629 (16)	0.0497 (6)
H10A	0.175423	0.766656	0.915743	0.060*
C11A	0.1767 (5)	0.70318 (19)	0.82900 (19)	0.0660 (9)
H11A	0.211897	0.739990	0.799033	0.079*
H11B	0.232219	0.662215	0.816088	0.079*
C12A	0.0132 (6)	0.6922 (3)	0.8156 (3)	0.0900 (14)
C13A	0.3872 (4)	0.72204 (16)	0.92029 (16)	0.0516 (6)
H13A	0.429086	0.677270	0.907799	0.062*
C14A	0.4748 (5)	0.7764 (2)	0.8800 (2)	0.0758 (10)
H14A	0.496154	0.760734	0.832585	0.091*
H14B	0.415111	0.818099	0.876880	0.091*
C15A	0.6232 (5)	0.7888 (3)	0.9208 (3)	0.0904 (13)
H15A	0.642560	0.837353	0.925599	0.108*
H15B	0.708972	0.768025	0.896771	0.108*
C16A	0.6014 (5)	0.7561 (3)	0.9929 (2)	0.0822 (12)
H16A	0.664840	0.715662	0.997912	0.099*
H16B	0.628514	0.787954	1.030299	0.099*
C17A	0.4340 (4)	0.7377 (2)	0.99591 (18)	0.0697 (10)
H17A	0.374545	0.775528	1.014154	0.084*
H17B	0.418831	0.698207	1.025872	0.084*
N1B	0.9779 (3)	0.65858 (14)	0.50235 (18)	0.0628 (7)
H1B	1.002292	0.700277	0.493782	0.075*
C1B	0.9135 (4)	0.63499 (17)	0.5625 (2)	0.0646 (9)
H1BA	0.888099	0.662255	0.600827	0.078*
N2B	1.0594 (3)	0.60673 (15)	0.39383 (17)	0.0656 (7)
C2B	0.8910 (4)	0.56667 (17)	0.5595 (2)	0.0599 (8)
H2B	0.849802	0.539163	0.594480	0.072*
N3B	1.0232 (3)	0.48496 (14)	0.38960 (15)	0.0584 (6)
C3B	0.9433 (3)	0.54520 (15)	0.49183 (17)	0.0492 (6)
N4B	0.9287 (3)	0.30386 (13)	0.50606 (16)	0.0567 (6)
C4B	0.9971 (3)	0.60471 (15)	0.45804 (19)	0.0538 (7)
N5B	0.8374 (3)	0.33691 (12)	0.55286 (13)	0.0479 (5)
C5B	1.0672 (5)	0.54578 (19)	0.3642 (2)	0.0668 (9)
H5B	1.109299	0.544868	0.319409	0.080*
N6B	1.0550 (7)	0.3476 (3)	0.7169 (4)	0.156 (3)
C6B	0.9620 (3)	0.48437 (15)	0.45446 (17)	0.0478 (6)
C7B	0.9243 (3)	0.41745 (14)	0.48404 (16)	0.0468 (6)
C8B	0.9797 (4)	0.35318 (16)	0.46455 (18)	0.0559 (7)
H8B	1.044873	0.345894	0.426819	0.067*
C9B	0.8325 (3)	0.40383 (14)	0.54065 (16)	0.0497 (6)
H9B	0.776752	0.435757	0.566023	0.060*
C10B	0.7491 (4)	0.29975 (14)	0.60584 (15)	0.0482 (6)
H10B	0.688873	0.333551	0.631686	0.058*
C11B	0.8572 (5)	0.26493 (17)	0.65955 (17)	0.0623 (8)
H11C	0.796065	0.244549	0.696407	0.075*
H11D	0.911448	0.228383	0.636018	0.075*
C12B	0.9684 (5)	0.3106 (2)	0.6918 (3)	0.0858 (13)
C13B	0.6357 (4)	0.24987 (16)	0.57170 (15)	0.0507 (6)
H13B	0.692601	0.212403	0.549911	0.061*
C14B	0.5233 (5)	0.2205 (3)	0.6252 (2)	0.0822 (12)
H14C	0.549478	0.173594	0.636364	0.099*
H14D	0.526073	0.247052	0.668433	0.099*
C15B	0.3670 (6)	0.2243 (6)	0.5908 (4)	0.152 (4)
H15C	0.300186	0.253206	0.618421	0.183*
H15D	0.321869	0.179132	0.587978	0.183*
C16B	0.3848 (6)	0.2537 (4)	0.5175 (4)	0.127 (3)
H16C	0.375919	0.217979	0.482211	0.153*
H16D	0.306175	0.287730	0.508015	0.153*
C17B	0.5347 (5)	0.2843 (2)	0.5159 (2)	0.0762 (10)
H17C	0.527421	0.332841	0.525483	0.091*
H17D	0.578862	0.278391	0.469532	0.091*
N1C	0.3464 (4)	0.07145 (15)	0.76582 (17)	0.0656 (7)
H1C	0.341691	0.029130	0.753859	0.079*
C1C	0.2242 (5)	0.1146 (2)	0.7704 (2)	0.0745 (10)
H1CA	0.122574	0.102097	0.761997	0.089*
N2C	0.6177 (3)	0.07957 (14)	0.78667 (15)	0.0589 (6)
C2C	0.2712 (4)	0.1787 (2)	0.7890 (2)	0.0671 (9)
H2C	0.209841	0.217091	0.794782	0.081*
N3C	0.6993 (3)	0.19311 (14)	0.81750 (15)	0.0581 (6)
C3C	0.4327 (4)	0.17461 (17)	0.79761 (16)	0.0537 (7)
N4C	0.4257 (3)	0.39835 (14)	0.80927 (15)	0.0568 (6)
C4C	0.4764 (4)	0.10579 (15)	0.78310 (15)	0.0510 (7)
N5C	0.5651 (3)	0.40124 (12)	0.84086 (13)	0.0488 (5)
C5C	0.7211 (4)	0.1269 (2)	0.80606 (19)	0.0647 (8)
H5C	0.821234	0.111335	0.812357	0.078*
N6C	0.7231 (5)	0.4579 (2)	0.68906 (19)	0.0893 (11)
C6C	0.5537 (4)	0.21917 (16)	0.81223 (15)	0.0507 (7)
C7C	0.5329 (4)	0.29255 (16)	0.81936 (15)	0.0505 (6)
C8C	0.4065 (4)	0.33207 (17)	0.79678 (19)	0.0607 (8)
H8C	0.318861	0.313797	0.775414	0.073*
C9C	0.6336 (4)	0.33973 (16)	0.84666 (16)	0.0519 (7)
H9C	0.730731	0.330982	0.865584	0.062*
C10C	0.6220 (3)	0.46888 (15)	0.86155 (16)	0.0499 (6)
H10C	0.543482	0.502087	0.847104	0.060*
C11C	0.7685 (5)	0.4864 (2)	0.82084 (19)	0.0686 (9)
H11E	0.793479	0.534213	0.827540	0.082*
H11F	0.853647	0.459388	0.839114	0.082*
C12C	0.7463 (5)	0.4724 (2)	0.7456 (2)	0.0677 (9)
C13C	0.6445 (3)	0.47615 (16)	0.94076 (16)	0.0520 (7)
H13C	0.734987	0.449669	0.955378	0.062*
C14C	0.6674 (5)	0.55071 (19)	0.9640 (2)	0.0680 (9)
H14E	0.774960	0.563360	0.962025	0.082*
H14F	0.608536	0.581326	0.933818	0.082*
C15C	0.6109 (7)	0.5539 (3)	1.0395 (2)	0.0913 (14)
H15E	0.697124	0.558313	1.072121	0.110*
H15F	0.543968	0.592968	1.045360	0.110*
C16C	0.5255 (7)	0.4896 (3)	1.0538 (2)	0.0994 (16)
H16E	0.425380	0.499725	1.072935	0.119*
H16F	0.581898	0.461530	1.087478	0.119*
C17C	0.5086 (5)	0.4527 (2)	0.9834 (2)	0.0789 (11)
H17E	0.510978	0.403646	0.990061	0.095*
H17F	0.412830	0.465075	0.959929	0.095*
N1D	0.6319 (4)	0.93258 (16)	0.74384 (16)	0.0671 (7)
H1D	0.638725	0.974390	0.757387	0.081*
C1D	0.7516 (5)	0.8879 (2)	0.7396 (3)	0.0804 (11)
H1DA	0.853097	0.898758	0.750584	0.096*
N2D	0.3616 (3)	0.92815 (14)	0.71904 (15)	0.0583 (6)
C2D	0.7034 (4)	0.8255 (2)	0.7173 (2)	0.0719 (10)
H2D	0.762903	0.786689	0.710498	0.086*
N3D	0.2763 (3)	0.81756 (14)	0.68095 (15)	0.0570 (6)
C3D	0.5416 (4)	0.83243 (16)	0.70646 (16)	0.0534 (7)
N4D	0.5219 (4)	0.60688 (15)	0.68219 (19)	0.0709 (8)
C4D	0.5001 (4)	0.90056 (15)	0.72327 (15)	0.0513 (7)
N5D	0.3861 (3)	0.61066 (13)	0.64707 (13)	0.0508 (6)
C5D	0.2563 (4)	0.88334 (19)	0.69560 (19)	0.0636 (8)
H5D	0.157447	0.900271	0.688775	0.076*
N6D	0.1493 (8)	0.5419 (2)	0.7819 (2)	0.1213 (19)
C6D	0.4198 (4)	0.79050 (16)	0.68752 (14)	0.0500 (6)
C7D	0.4355 (4)	0.71652 (15)	0.67592 (15)	0.0512 (7)
C8D	0.5518 (5)	0.67172 (19)	0.6988 (2)	0.0677 (9)
H8D	0.640058	0.685754	0.722966	0.081*
C9D	0.3309 (4)	0.67452 (15)	0.64292 (16)	0.0519 (7)
H9D	0.238736	0.687823	0.621613	0.062*
C10D	0.3191 (4)	0.54834 (14)	0.61708 (16)	0.0485 (6)
H10D	0.217986	0.559626	0.596894	0.058*
C11D	0.2973 (4)	0.49458 (15)	0.67537 (18)	0.0595 (8)
H11G	0.242654	0.455701	0.655618	0.071*
H11H	0.397288	0.478807	0.691618	0.071*
C12D	0.2134 (6)	0.5204 (2)	0.7350 (2)	0.0800 (12)
C13D	0.4188 (3)	0.52042 (15)	0.55824 (16)	0.0492 (6)
H13D	0.518898	0.507467	0.578406	0.059*
C14D	0.3487 (5)	0.45843 (18)	0.52102 (19)	0.0645 (8)
H14G	0.370377	0.417057	0.547509	0.077*
H14H	0.238347	0.463531	0.515996	0.077*
C15D	0.4235 (6)	0.4557 (2)	0.4489 (2)	0.0767 (11)
H15G	0.506032	0.422460	0.448949	0.092*
H15H	0.348676	0.443058	0.412775	0.092*
C16D	0.4859 (7)	0.5268 (2)	0.4348 (2)	0.0886 (13)
H16G	0.596450	0.525379	0.429548	0.106*
H16H	0.440345	0.545478	0.391902	0.106*
C17D	0.4440 (5)	0.5699 (2)	0.4976 (2)	0.0726 (10)
H17G	0.351267	0.595760	0.487683	0.087*
H17H	0.526248	0.601513	0.509247	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0673 (16)	0.0324 (13)	0.0829 (19)	−0.0026 (11)	0.0093 (14)	0.0073 (12)
C1A	0.0700 (19)	0.0392 (16)	0.074 (2)	−0.0013 (14)	0.0100 (16)	−0.0021 (14)
N2A	0.0792 (18)	0.0454 (16)	0.0732 (18)	−0.0019 (13)	0.0151 (14)	0.0198 (13)
C2A	0.0599 (17)	0.0404 (16)	0.0656 (18)	−0.0034 (12)	0.0091 (14)	0.0056 (13)
N3A	0.0749 (17)	0.0492 (16)	0.0635 (16)	−0.0014 (13)	0.0149 (13)	0.0061 (13)
C3A	0.0434 (13)	0.0336 (14)	0.0631 (16)	−0.0005 (10)	0.0036 (12)	0.0071 (12)
N4A	0.0675 (15)	0.0341 (13)	0.0606 (15)	0.0043 (10)	0.0136 (12)	−0.0046 (10)
C4A	0.0507 (14)	0.0381 (15)	0.0698 (19)	0.0015 (12)	0.0052 (13)	0.0114 (14)
N5A	0.0571 (13)	0.0282 (11)	0.0583 (14)	0.0002 (9)	0.0111 (11)	−0.0007 (10)
C5A	0.087 (2)	0.059 (2)	0.064 (2)	−0.0026 (18)	0.0192 (17)	0.0152 (17)
N6A	0.102 (3)	0.124 (4)	0.208 (6)	0.016 (3)	−0.071 (4)	−0.035 (4)
C6A	0.0493 (14)	0.0387 (15)	0.0598 (17)	0.0007 (11)	0.0034 (12)	0.0063 (12)
C7A	0.0524 (14)	0.0339 (14)	0.0566 (16)	−0.0017 (11)	0.0021 (12)	0.0013 (12)
C8A	0.0657 (17)	0.0404 (16)	0.0606 (18)	−0.0005 (13)	0.0133 (14)	0.0005 (13)
C9A	0.0575 (15)	0.0299 (13)	0.0646 (18)	0.0009 (12)	0.0135 (13)	−0.0021 (12)
C10A	0.0647 (16)	0.0287 (13)	0.0558 (15)	−0.0015 (11)	0.0095 (13)	0.0021 (11)
C11A	0.083 (2)	0.0548 (19)	0.0598 (19)	−0.0058 (17)	−0.0062 (16)	0.0053 (15)
C12A	0.097 (3)	0.067 (3)	0.104 (3)	0.009 (2)	−0.036 (3)	−0.001 (2)
C13A	0.0621 (16)	0.0409 (15)	0.0520 (15)	−0.0046 (12)	0.0100 (12)	−0.0025 (12)
C14A	0.086 (2)	0.074 (3)	0.067 (2)	−0.026 (2)	0.0130 (18)	0.0113 (18)
C15A	0.082 (3)	0.089 (3)	0.101 (3)	−0.028 (2)	0.028 (2)	−0.016 (3)
C16A	0.075 (2)	0.088 (3)	0.083 (3)	−0.020 (2)	−0.004 (2)	−0.009 (2)
C17A	0.076 (2)	0.080 (3)	0.0525 (18)	−0.0173 (19)	0.0025 (15)	0.0017 (17)
N1B	0.0639 (16)	0.0308 (12)	0.094 (2)	−0.0033 (11)	0.0107 (14)	0.0024 (13)
C1B	0.070 (2)	0.0392 (17)	0.085 (2)	0.0014 (14)	0.0134 (17)	−0.0081 (16)
N2B	0.0761 (17)	0.0418 (15)	0.0794 (19)	−0.0030 (13)	0.0130 (14)	0.0140 (14)
C2B	0.0675 (19)	0.0377 (16)	0.075 (2)	−0.0048 (13)	0.0158 (16)	−0.0006 (14)
N3B	0.0675 (15)	0.0431 (15)	0.0648 (16)	−0.0012 (11)	0.0105 (12)	0.0060 (12)
C3B	0.0496 (14)	0.0327 (14)	0.0655 (17)	−0.0005 (11)	0.0048 (12)	0.0047 (12)
N4B	0.0711 (15)	0.0307 (12)	0.0688 (16)	0.0046 (11)	0.0187 (12)	−0.0026 (11)
C4B	0.0512 (14)	0.0304 (14)	0.080 (2)	0.0000 (11)	0.0034 (14)	0.0067 (14)
N5B	0.0641 (14)	0.0261 (11)	0.0539 (13)	0.0018 (9)	0.0115 (11)	−0.0010 (9)
C5B	0.082 (2)	0.0504 (19)	0.069 (2)	−0.0056 (16)	0.0148 (17)	0.0114 (16)
N6B	0.129 (4)	0.104 (4)	0.233 (7)	−0.003 (3)	−0.099 (5)	−0.029 (4)
C6B	0.0490 (14)	0.0313 (14)	0.0634 (17)	−0.0012 (11)	0.0060 (12)	0.0053 (12)
C7B	0.0539 (14)	0.0294 (13)	0.0573 (16)	−0.0012 (11)	0.0071 (12)	0.0017 (12)
C8B	0.0679 (18)	0.0360 (16)	0.0642 (19)	0.0016 (13)	0.0193 (15)	0.0004 (13)
C9B	0.0620 (15)	0.0266 (13)	0.0607 (17)	0.0002 (11)	0.0091 (13)	−0.0034 (12)
C10B	0.0673 (17)	0.0302 (13)	0.0474 (14)	−0.0007 (11)	0.0096 (12)	0.0000 (11)
C11B	0.089 (2)	0.0439 (17)	0.0542 (17)	−0.0003 (15)	−0.0040 (15)	−0.0013 (14)
C12B	0.084 (3)	0.066 (3)	0.107 (3)	0.011 (2)	−0.029 (2)	−0.015 (2)
C13B	0.0674 (17)	0.0390 (14)	0.0459 (14)	−0.0055 (12)	0.0064 (12)	−0.0021 (11)
C14B	0.103 (3)	0.083 (3)	0.061 (2)	−0.039 (2)	0.020 (2)	−0.0045 (19)
C15B	0.069 (3)	0.260 (11)	0.129 (5)	−0.022 (4)	0.035 (3)	−0.028 (6)
C16B	0.084 (3)	0.101 (4)	0.196 (7)	−0.015 (3)	−0.035 (4)	0.042 (5)
C17B	0.090 (3)	0.074 (3)	0.064 (2)	0.009 (2)	−0.0096 (18)	0.0013 (18)
N1C	0.0786 (18)	0.0400 (14)	0.0786 (18)	−0.0083 (13)	0.0076 (14)	−0.0100 (13)
C1C	0.072 (2)	0.055 (2)	0.098 (3)	−0.0107 (17)	0.0081 (19)	−0.0091 (19)
N2C	0.0770 (17)	0.0430 (14)	0.0569 (15)	−0.0049 (13)	0.0051 (13)	−0.0046 (11)
C2C	0.0636 (19)	0.054 (2)	0.084 (2)	−0.0002 (15)	0.0080 (17)	−0.0096 (18)
N3C	0.0657 (15)	0.0482 (16)	0.0602 (15)	−0.0009 (12)	−0.0036 (12)	−0.0049 (12)
C3C	0.0685 (18)	0.0437 (17)	0.0490 (15)	−0.0033 (13)	0.0092 (13)	0.0006 (13)
N4C	0.0642 (15)	0.0401 (13)	0.0658 (16)	−0.0015 (11)	−0.0111 (12)	−0.0045 (12)
C4C	0.0759 (19)	0.0331 (14)	0.0441 (14)	−0.0082 (13)	0.0105 (13)	−0.0015 (11)
N5C	0.0613 (13)	0.0338 (12)	0.0510 (13)	0.0023 (10)	−0.0050 (10)	−0.0063 (10)
C5C	0.073 (2)	0.056 (2)	0.0650 (19)	−0.0014 (16)	0.0010 (16)	−0.0029 (15)
N6C	0.131 (3)	0.074 (2)	0.063 (2)	0.023 (2)	0.0199 (19)	−0.0033 (17)
C6C	0.0711 (18)	0.0416 (16)	0.0396 (13)	−0.0042 (13)	0.0043 (12)	−0.0006 (12)
C7C	0.0713 (17)	0.0368 (15)	0.0436 (14)	−0.0002 (13)	0.0053 (12)	−0.0008 (11)
C8C	0.074 (2)	0.0417 (17)	0.0662 (19)	−0.0120 (14)	−0.0098 (15)	−0.0062 (14)
C9C	0.0669 (17)	0.0374 (15)	0.0511 (16)	0.0059 (13)	−0.0053 (13)	−0.0033 (12)
C10C	0.0612 (16)	0.0357 (14)	0.0526 (15)	−0.0002 (12)	−0.0033 (12)	−0.0062 (12)
C11C	0.081 (2)	0.060 (2)	0.065 (2)	−0.0143 (17)	0.0070 (17)	−0.0056 (16)
C12C	0.091 (2)	0.0479 (18)	0.064 (2)	0.0072 (17)	0.0163 (17)	0.0012 (16)
C13C	0.0566 (15)	0.0447 (16)	0.0545 (16)	0.0025 (12)	−0.0057 (12)	−0.0066 (13)
C14C	0.081 (2)	0.052 (2)	0.072 (2)	−0.0070 (16)	−0.0079 (17)	−0.0172 (16)
C15C	0.123 (4)	0.076 (3)	0.075 (3)	0.005 (3)	0.001 (2)	−0.032 (2)
C16C	0.125 (4)	0.104 (4)	0.070 (2)	−0.021 (3)	0.025 (2)	−0.026 (3)
C17C	0.094 (3)	0.076 (3)	0.067 (2)	−0.022 (2)	0.0129 (19)	−0.0160 (19)
N1D	0.0804 (19)	0.0457 (16)	0.0752 (18)	−0.0108 (13)	0.0008 (15)	−0.0052 (13)
C1D	0.074 (2)	0.064 (3)	0.103 (3)	−0.0107 (19)	−0.008 (2)	−0.003 (2)
N2D	0.0769 (17)	0.0368 (13)	0.0614 (15)	−0.0022 (12)	0.0051 (13)	−0.0055 (11)
C2D	0.064 (2)	0.065 (2)	0.087 (3)	0.0018 (17)	−0.0007 (17)	0.0015 (19)
N3D	0.0666 (15)	0.0431 (14)	0.0611 (15)	0.0040 (12)	−0.0033 (12)	−0.0058 (11)
C3D	0.0726 (19)	0.0386 (16)	0.0490 (15)	−0.0022 (13)	0.0065 (13)	0.0040 (12)
N4D	0.0788 (18)	0.0386 (14)	0.094 (2)	0.0026 (13)	−0.0273 (16)	−0.0102 (14)
C4D	0.0762 (19)	0.0334 (14)	0.0445 (14)	−0.0077 (13)	0.0060 (13)	0.0032 (11)
N5D	0.0645 (14)	0.0321 (12)	0.0556 (13)	0.0044 (11)	−0.0070 (11)	−0.0041 (10)
C5D	0.073 (2)	0.0483 (18)	0.069 (2)	−0.0001 (15)	−0.0002 (16)	−0.0058 (15)
N6D	0.210 (6)	0.065 (2)	0.091 (3)	0.014 (3)	0.069 (3)	0.002 (2)
C6D	0.0690 (17)	0.0396 (15)	0.0414 (14)	−0.0008 (13)	0.0008 (12)	0.0025 (11)
C7D	0.0722 (18)	0.0345 (15)	0.0468 (14)	−0.0015 (13)	0.0015 (13)	−0.0018 (11)
C8D	0.079 (2)	0.0480 (19)	0.076 (2)	−0.0072 (16)	−0.0174 (18)	−0.0121 (16)
C9D	0.0674 (17)	0.0350 (14)	0.0531 (16)	0.0048 (12)	−0.0007 (13)	−0.0010 (12)
C10D	0.0589 (15)	0.0330 (13)	0.0536 (15)	0.0038 (11)	−0.0048 (12)	−0.0040 (11)
C11D	0.086 (2)	0.0330 (15)	0.0603 (17)	0.0008 (14)	0.0112 (16)	−0.0040 (12)
C12D	0.127 (3)	0.0436 (19)	0.070 (2)	0.000 (2)	0.025 (2)	−0.0003 (16)
C13D	0.0543 (15)	0.0373 (14)	0.0558 (16)	0.0050 (11)	−0.0043 (12)	−0.0052 (12)
C14D	0.082 (2)	0.0456 (18)	0.0659 (19)	0.0000 (15)	0.0020 (16)	−0.0154 (15)
C15D	0.114 (3)	0.057 (2)	0.0597 (19)	0.013 (2)	0.0016 (19)	−0.0098 (16)
C16D	0.125 (4)	0.072 (3)	0.069 (2)	0.004 (3)	0.017 (2)	−0.003 (2)
C17D	0.101 (3)	0.0506 (19)	0.067 (2)	0.0013 (18)	0.0105 (19)	0.0009 (16)

Geometric parameters (Å, º)

N1A—H1A	0.8600	N1C—H1C	0.8600
N1A—C1A	1.371 (5)	N1C—C1C	1.364 (5)
N1A—C4A	1.359 (5)	N1C—C4C	1.353 (4)
C1A—H1AA	0.9300	C1C—H1CA	0.9300
C1A—C2A	1.358 (5)	C1C—C2C	1.364 (6)
N2A—C4A	1.323 (4)	N2C—C4C	1.335 (4)
N2A—C5A	1.336 (5)	N2C—C5C	1.339 (5)
C2A—H2A	0.9300	C2C—H2C	0.9300
C2A—C3A	1.424 (5)	C2C—C3C	1.416 (5)
N3A—C5A	1.336 (5)	N3C—C5C	1.329 (5)
N3A—C6A	1.356 (4)	N3C—C6C	1.370 (4)
C3A—C4A	1.419 (4)	C3C—C4C	1.428 (4)
C3A—C6A	1.396 (4)	C3C—C6C	1.393 (5)
N4A—N5A	1.355 (4)	N4C—N5C	1.346 (4)
N4A—C8A	1.322 (4)	N4C—C8C	1.330 (4)
N5A—C9A	1.348 (4)	N5C—C9C	1.348 (4)
N5A—C10A	1.463 (4)	N5C—C10C	1.466 (4)
C5A—H5A	0.9300	C5C—H5C	0.9300
N6A—C12A	1.126 (7)	N6C—C12C	1.123 (5)
C6A—C7A	1.461 (4)	C6C—C7C	1.455 (4)
C7A—C8A	1.407 (4)	C7C—C8C	1.407 (5)
C7A—C9A	1.374 (4)	C7C—C9C	1.370 (5)
C8A—H8A	0.9300	C8C—H8C	0.9300
C9A—H9A	0.9300	C9C—H9C	0.9300
C10A—H10A	0.9800	C10C—H10C	0.9800
C10A—C11A	1.536 (5)	C10C—C11C	1.539 (5)
C10A—C13A	1.516 (4)	C10C—C13C	1.516 (4)
C11A—H11A	0.9700	C11C—H11E	0.9700
C11A—H11B	0.9700	C11C—H11F	0.9700
C11A—C12A	1.459 (6)	C11C—C12C	1.461 (5)
C13A—H13A	0.9800	C13C—H13C	0.9800
C13A—C14A	1.521 (5)	C13C—C14C	1.538 (5)
C13A—C17A	1.515 (4)	C13C—C17C	1.514 (5)
C14A—H14A	0.9700	C14C—H14E	0.9700
C14A—H14B	0.9700	C14C—H14F	0.9700
C14A—C15A	1.515 (6)	C14C—C15C	1.520 (6)
C15A—H15A	0.9700	C15C—H15E	0.9700
C15A—H15B	0.9700	C15C—H15F	0.9700
C15A—C16A	1.523 (7)	C15C—C16C	1.489 (8)
C16A—H16A	0.9700	C16C—H16E	0.9700
C16A—H16B	0.9700	C16C—H16F	0.9700
C16A—C17A	1.504 (5)	C16C—C17C	1.521 (6)
C17A—H17A	0.9700	C17C—H17E	0.9700
C17A—H17B	0.9700	C17C—H17F	0.9700
N1B—H1B	0.8600	N1D—H1D	0.8600
N1B—C1B	1.359 (5)	N1D—C1D	1.365 (6)
N1B—C4B	1.360 (5)	N1D—C4D	1.360 (4)
C1B—H1BA	0.9300	C1D—H1DA	0.9300
C1B—C2B	1.353 (5)	C1D—C2D	1.357 (6)
N2B—C4B	1.340 (5)	N2D—C4D	1.323 (4)
N2B—C5B	1.321 (5)	N2D—C5D	1.340 (5)
C2B—H2B	0.9300	C2D—H2D	0.9300
C2B—C3B	1.430 (5)	C2D—C3D	1.428 (5)
N3B—C5B	1.342 (4)	N3D—C5D	1.330 (5)
N3B—C6B	1.346 (4)	N3D—C6D	1.362 (4)
C3B—C4B	1.413 (4)	C3D—C4D	1.420 (4)
C3B—C6B	1.396 (4)	C3D—C6D	1.384 (5)
N4B—N5B	1.363 (4)	N4D—N5D	1.350 (4)
N4B—C8B	1.326 (4)	N4D—C8D	1.333 (5)
N5B—C9B	1.332 (4)	N5D—C9D	1.342 (4)
N5B—C10B	1.467 (4)	N5D—C10D	1.464 (4)
C5B—H5B	0.9300	C5D—H5D	0.9300
N6B—C12B	1.145 (7)	N6D—C12D	1.136 (6)
C6B—C7B	1.465 (4)	C6D—C7D	1.472 (4)
C7B—C8B	1.400 (4)	C7D—C8D	1.404 (5)
C7B—C9B	1.373 (4)	C7D—C9D	1.371 (5)
C8B—H8B	0.9300	C8D—H8D	0.9300
C9B—H9B	0.9300	C9D—H9D	0.9300
C10B—H10B	0.9800	C10D—H10D	0.9800
C10B—C11B	1.535 (4)	C10D—C11D	1.539 (4)
C10B—C13B	1.526 (4)	C10D—C13D	1.525 (4)
C11B—H11C	0.9700	C11D—H11G	0.9700
C11B—H11D	0.9700	C11D—H11H	0.9700
C11B—C12B	1.446 (6)	C11D—C12D	1.446 (5)
C13B—H13B	0.9800	C13D—H13D	0.9800
C13B—C14B	1.531 (5)	C13D—C14D	1.527 (4)
C13B—C17B	1.523 (5)	C13D—C17D	1.520 (5)
C14B—H14C	0.9700	C14D—H14G	0.9700
C14B—H14D	0.9700	C14D—H14H	0.9700
C14B—C15B	1.502 (8)	C14D—C15D	1.523 (5)
C15B—H15C	0.9700	C15D—H15G	0.9700
C15B—H15D	0.9700	C15D—H15H	0.9700
C15B—C16B	1.514 (9)	C15D—C16D	1.520 (6)
C16B—H16C	0.9700	C16D—H16G	0.9700
C16B—H16D	0.9700	C16D—H16H	0.9700
C16B—C17B	1.438 (7)	C16D—C17D	1.507 (6)
C17B—H17C	0.9700	C17D—H17G	0.9700
C17B—H17D	0.9700	C17D—H17H	0.9700
C1A—N1A—H1A	125.8	C1C—N1C—H1C	125.4
C4A—N1A—H1A	125.8	C4C—N1C—H1C	125.4
C4A—N1A—C1A	108.4 (3)	C4C—N1C—C1C	109.1 (3)
N1A—C1A—H1AA	124.7	N1C—C1C—H1CA	124.6
C2A—C1A—N1A	110.5 (3)	N1C—C1C—C2C	110.8 (3)
C2A—C1A—H1AA	124.7	C2C—C1C—H1CA	124.6
C4A—N2A—C5A	112.3 (3)	C4C—N2C—C5C	111.3 (3)
C1A—C2A—H2A	126.7	C1C—C2C—H2C	127.1
C1A—C2A—C3A	106.6 (3)	C1C—C2C—C3C	105.8 (3)
C3A—C2A—H2A	126.7	C3C—C2C—H2C	127.1
C5A—N3A—C6A	117.5 (3)	C5C—N3C—C6C	119.1 (3)
C4A—C3A—C2A	106.5 (3)	C2C—C3C—C4C	107.3 (3)
C6A—C3A—C2A	137.8 (3)	C6C—C3C—C2C	137.3 (3)
C6A—C3A—C4A	115.6 (3)	C6C—C3C—C4C	115.2 (3)
C8A—N4A—N5A	105.4 (2)	C8C—N4C—N5C	103.3 (3)
N1A—C4A—C3A	108.0 (3)	N1C—C4C—C3C	106.9 (3)
N2A—C4A—N1A	126.0 (3)	N2C—C4C—N1C	126.1 (3)
N2A—C4A—C3A	126.0 (3)	N2C—C4C—C3C	127.0 (3)
N4A—N5A—C10A	119.5 (2)	N4C—N5C—C9C	113.2 (2)
C9A—N5A—N4A	111.2 (2)	N4C—N5C—C10C	117.1 (2)
C9A—N5A—C10A	129.0 (2)	C9C—N5C—C10C	129.7 (3)
N2A—C5A—H5A	115.5	N2C—C5C—H5C	115.7
N3A—C5A—N2A	128.9 (3)	N3C—C5C—N2C	128.5 (4)
N3A—C5A—H5A	115.5	N3C—C5C—H5C	115.7
N3A—C6A—C3A	119.7 (3)	N3C—C6C—C3C	118.6 (3)
N3A—C6A—C7A	116.2 (3)	N3C—C6C—C7C	118.6 (3)
C3A—C6A—C7A	124.0 (3)	C3C—C6C—C7C	122.8 (3)
C8A—C7A—C6A	126.0 (3)	C8C—C7C—C6C	127.8 (3)
C9A—C7A—C6A	129.7 (3)	C9C—C7C—C6C	128.4 (3)
C9A—C7A—C8A	104.1 (3)	C9C—C7C—C8C	103.7 (3)
N4A—C8A—C7A	111.6 (3)	N4C—C8C—C7C	112.8 (3)
N4A—C8A—H8A	124.2	N4C—C8C—H8C	123.6
C7A—C8A—H8A	124.2	C7C—C8C—H8C	123.6
N5A—C9A—C7A	107.7 (3)	N5C—C9C—C7C	107.0 (3)
N5A—C9A—H9A	126.1	N5C—C9C—H9C	126.5
C7A—C9A—H9A	126.1	C7C—C9C—H9C	126.5
N5A—C10A—H10A	107.9	N5C—C10C—H10C	107.0
N5A—C10A—C11A	110.5 (3)	N5C—C10C—C11C	110.3 (3)
N5A—C10A—C13A	110.8 (2)	N5C—C10C—C13C	112.8 (3)
C11A—C10A—H10A	107.9	C11C—C10C—H10C	107.0
C13A—C10A—H10A	107.9	C13C—C10C—H10C	107.0
C13A—C10A—C11A	111.8 (3)	C13C—C10C—C11C	112.3 (3)
C10A—C11A—H11A	108.9	C10C—C11C—H11E	109.6
C10A—C11A—H11B	108.9	C10C—C11C—H11F	109.6
H11A—C11A—H11B	107.7	H11E—C11C—H11F	108.1
C12A—C11A—C10A	113.5 (3)	C12C—C11C—C10C	110.4 (3)
C12A—C11A—H11A	108.9	C12C—C11C—H11E	109.6
C12A—C11A—H11B	108.9	C12C—C11C—H11F	109.6
N6A—C12A—C11A	178.5 (6)	N6C—C12C—C11C	175.2 (5)
C10A—C13A—H13A	108.3	C10C—C13C—H13C	108.7
C10A—C13A—C14A	115.1 (3)	C10C—C13C—C14C	112.7 (3)
C14A—C13A—H13A	108.3	C14C—C13C—H13C	108.7
C17A—C13A—C10A	114.8 (3)	C17C—C13C—C10C	114.1 (3)
C17A—C13A—H13A	108.3	C17C—C13C—H13C	108.7
C17A—C13A—C14A	101.7 (3)	C17C—C13C—C14C	103.6 (3)
C13A—C14A—H14A	110.4	C13C—C14C—H14E	110.7
C13A—C14A—H14B	110.4	C13C—C14C—H14F	110.7
H14A—C14A—H14B	108.6	H14E—C14C—H14F	108.8
C15A—C14A—C13A	106.7 (3)	C15C—C14C—C13C	105.4 (3)
C15A—C14A—H14A	110.4	C15C—C14C—H14E	110.7
C15A—C14A—H14B	110.4	C15C—C14C—H14F	110.7
C14A—C15A—H15A	110.6	C14C—C15C—H15E	110.1
C14A—C15A—H15B	110.6	C14C—C15C—H15F	110.1
C14A—C15A—C16A	105.8 (3)	H15E—C15C—H15F	108.4
H15A—C15A—H15B	108.7	C16C—C15C—C14C	107.9 (3)
C16A—C15A—H15A	110.6	C16C—C15C—H15E	110.1
C16A—C15A—H15B	110.6	C16C—C15C—H15F	110.1
C15A—C16A—H16A	110.6	C15C—C16C—H16E	110.4
C15A—C16A—H16B	110.6	C15C—C16C—H16F	110.4
H16A—C16A—H16B	108.8	C15C—C16C—C17C	106.5 (4)
C17A—C16A—C15A	105.6 (3)	H16E—C16C—H16F	108.6
C17A—C16A—H16A	110.6	C17C—C16C—H16E	110.4
C17A—C16A—H16B	110.6	C17C—C16C—H16F	110.4
C13A—C17A—H17A	110.7	C13C—C17C—C16C	104.9 (3)
C13A—C17A—H17B	110.7	C13C—C17C—H17E	110.8
C16A—C17A—C13A	105.1 (3)	C13C—C17C—H17F	110.8
C16A—C17A—H17A	110.7	C16C—C17C—H17E	110.8
C16A—C17A—H17B	110.7	C16C—C17C—H17F	110.8
H17A—C17A—H17B	108.8	H17E—C17C—H17F	108.8
C1B—N1B—H1B	126.0	C1D—N1D—H1D	125.4
C1B—N1B—C4B	108.0 (3)	C4D—N1D—H1D	125.4
C4B—N1B—H1B	126.0	C4D—N1D—C1D	109.3 (3)
N1B—C1B—H1BA	124.4	N1D—C1D—H1DA	124.4
C2B—C1B—N1B	111.2 (3)	C2D—C1D—N1D	111.3 (4)
C2B—C1B—H1BA	124.4	C2D—C1D—H1DA	124.4
C5B—N2B—C4B	112.5 (3)	C4D—N2D—C5D	111.8 (3)
C1B—C2B—H2B	126.8	C1D—C2D—H2D	127.5
C1B—C2B—C3B	106.3 (3)	C1D—C2D—C3D	105.0 (4)
C3B—C2B—H2B	126.8	C3D—C2D—H2D	127.5
C5B—N3B—C6B	116.9 (3)	C5D—N3D—C6D	118.7 (3)
C4B—C3B—C2B	106.0 (3)	C4D—C3D—C2D	108.1 (3)
C6B—C3B—C2B	138.3 (3)	C6D—C3D—C2D	137.0 (3)
C6B—C3B—C4B	115.6 (3)	C6D—C3D—C4D	114.8 (3)
C8B—N4B—N5B	104.1 (2)	C8D—N4D—N5D	103.3 (3)
N1B—C4B—C3B	108.4 (3)	N1D—C4D—C3D	106.3 (3)
N2B—C4B—N1B	126.3 (3)	N2D—C4D—N1D	126.4 (3)
N2B—C4B—C3B	125.2 (3)	N2D—C4D—C3D	127.2 (3)
N4B—N5B—C10B	121.8 (2)	N4D—N5D—C10D	119.1 (2)
C9B—N5B—N4B	111.8 (2)	C9D—N5D—N4D	113.0 (3)
C9B—N5B—C10B	126.3 (2)	C9D—N5D—C10D	127.8 (3)
N2B—C5B—N3B	129.3 (3)	N2D—C5D—H5D	116.1
N2B—C5B—H5B	115.3	N3D—C5D—N2D	127.8 (3)
N3B—C5B—H5B	115.3	N3D—C5D—H5D	116.1
N3B—C6B—C3B	120.4 (3)	N3D—C6D—C3D	119.4 (3)
N3B—C6B—C7B	116.8 (3)	N3D—C6D—C7D	117.1 (3)
C3B—C6B—C7B	122.8 (3)	C3D—C6D—C7D	123.4 (3)
C8B—C7B—C6B	128.6 (3)	C8D—C7D—C6D	129.6 (3)
C9B—C7B—C6B	127.5 (3)	C9D—C7D—C6D	126.6 (3)
C9B—C7B—C8B	103.8 (3)	C9D—C7D—C8D	103.8 (3)
N4B—C8B—C7B	112.3 (3)	N4D—C8D—C7D	112.6 (3)
N4B—C8B—H8B	123.9	N4D—C8D—H8D	123.7
C7B—C8B—H8B	123.9	C7D—C8D—H8D	123.7
N5B—C9B—C7B	108.0 (3)	N5D—C9D—C7D	107.3 (3)
N5B—C9B—H9B	126.0	N5D—C9D—H9D	126.4
C7B—C9B—H9B	126.0	C7D—C9D—H9D	126.4
N5B—C10B—H10B	107.2	N5D—C10D—H10D	108.3
N5B—C10B—C11B	110.5 (3)	N5D—C10D—C11D	110.2 (2)
N5B—C10B—C13B	111.7 (2)	N5D—C10D—C13D	110.7 (3)
C11B—C10B—H10B	107.2	C11D—C10D—H10D	108.3
C13B—C10B—H10B	107.2	C13D—C10D—H10D	108.3
C13B—C10B—C11B	112.5 (2)	C13D—C10D—C11D	110.9 (2)
C10B—C11B—H11C	108.8	C10D—C11D—H11G	109.0
C10B—C11B—H11D	108.8	C10D—C11D—H11H	109.0
H11C—C11B—H11D	107.7	H11G—C11D—H11H	107.8
C12B—C11B—C10B	113.9 (3)	C12D—C11D—C10D	112.9 (3)
C12B—C11B—H11C	108.8	C12D—C11D—H11G	109.0
C12B—C11B—H11D	108.8	C12D—C11D—H11H	109.0
N6B—C12B—C11B	178.9 (5)	N6D—C12D—C11D	178.6 (5)
C10B—C13B—H13B	109.3	C10D—C13D—H13D	108.7
C10B—C13B—C14B	112.1 (3)	C10D—C13D—C14D	113.2 (3)
C14B—C13B—H13B	109.3	C14D—C13D—H13D	108.7
C17B—C13B—C10B	112.0 (3)	C17D—C13D—C10D	114.4 (3)
C17B—C13B—H13B	109.3	C17D—C13D—H13D	108.7
C17B—C13B—C14B	104.9 (3)	C17D—C13D—C14D	102.7 (3)
C13B—C14B—H14C	110.5	C13D—C14D—H14G	110.6
C13B—C14B—H14D	110.5	C13D—C14D—H14H	110.6
H14C—C14B—H14D	108.7	H14G—C14D—H14H	108.8
C15B—C14B—C13B	106.2 (4)	C15D—C14D—C13D	105.6 (3)
C15B—C14B—H14C	110.5	C15D—C14D—H14G	110.6
C15B—C14B—H14D	110.5	C15D—C14D—H14H	110.6
C14B—C15B—H15C	110.1	C14D—C15D—H15G	110.4
C14B—C15B—H15D	110.1	C14D—C15D—H15H	110.4
C14B—C15B—C16B	108.2 (4)	H15G—C15D—H15H	108.6
H15C—C15B—H15D	108.4	C16D—C15D—C14D	106.5 (3)
C16B—C15B—H15C	110.1	C16D—C15D—H15G	110.4
C16B—C15B—H15D	110.1	C16D—C15D—H15H	110.4
C15B—C16B—H16C	110.4	C15D—C16D—H16G	110.4
C15B—C16B—H16D	110.4	C15D—C16D—H16H	110.4
H16C—C16B—H16D	108.6	H16G—C16D—H16H	108.6
C17B—C16B—C15B	106.5 (5)	C17D—C16D—C15D	106.4 (4)
C17B—C16B—H16C	110.4	C17D—C16D—H16G	110.4
C17B—C16B—H16D	110.4	C17D—C16D—H16H	110.4
C13B—C17B—H17C	110.0	C13D—C17D—H17G	110.5
C13B—C17B—H17D	110.0	C13D—C17D—H17H	110.5
C16B—C17B—C13B	108.4 (4)	C16D—C17D—C13D	106.2 (3)
C16B—C17B—H17C	110.0	C16D—C17D—H17G	110.5
C16B—C17B—H17D	110.0	C16D—C17D—H17H	110.5
H17C—C17B—H17D	108.4	H17G—C17D—H17H	108.7
N1A—C1A—C2A—C3A	0.8 (4)	N1C—C1C—C2C—C3C	−1.0 (5)
C1A—N1A—C4A—N2A	177.9 (3)	C1C—N1C—C4C—N2C	177.8 (3)
C1A—N1A—C4A—C3A	0.7 (4)	C1C—N1C—C4C—C3C	−1.4 (4)
C1A—C2A—C3A—C4A	−0.3 (4)	C1C—C2C—C3C—C4C	0.1 (4)
C1A—C2A—C3A—C6A	−176.3 (3)	C1C—C2C—C3C—C6C	176.0 (4)
C2A—C3A—C4A—N1A	−0.3 (3)	C2C—C3C—C4C—N1C	0.8 (4)
C2A—C3A—C4A—N2A	−177.5 (3)	C2C—C3C—C4C—N2C	−178.4 (3)
C2A—C3A—C6A—N3A	177.8 (3)	C2C—C3C—C6C—N3C	178.8 (4)
C2A—C3A—C6A—C7A	1.2 (5)	C2C—C3C—C6C—C7C	−3.7 (6)
N3A—C6A—C7A—C8A	−17.7 (5)	N3C—C6C—C7C—C8C	160.4 (3)
N3A—C6A—C7A—C9A	168.0 (3)	N3C—C6C—C7C—C9C	−16.5 (5)
C3A—C6A—C7A—C8A	159.1 (3)	C3C—C6C—C7C—C8C	−17.1 (5)
C3A—C6A—C7A—C9A	−15.2 (5)	C3C—C6C—C7C—C9C	166.0 (3)
N4A—N5A—C9A—C7A	−0.3 (4)	N4C—N5C—C9C—C7C	−1.9 (4)
N4A—N5A—C10A—C11A	−130.0 (3)	N4C—N5C—C10C—C11C	−116.9 (3)
N4A—N5A—C10A—C13A	105.5 (3)	N4C—N5C—C10C—C13C	116.7 (3)
C4A—N1A—C1A—C2A	−1.0 (4)	C4C—N1C—C1C—C2C	1.6 (5)
C4A—N2A—C5A—N3A	0.6 (6)	C4C—N2C—C5C—N3C	−3.7 (5)
C4A—C3A—C6A—N3A	2.1 (4)	C4C—C3C—C6C—N3C	−5.5 (4)
C4A—C3A—C6A—C7A	−174.6 (3)	C4C—C3C—C6C—C7C	172.0 (3)
N5A—N4A—C8A—C7A	0.0 (4)	N5C—N4C—C8C—C7C	−0.7 (4)
N5A—C10A—C11A—C12A	48.1 (4)	N5C—C10C—C11C—C12C	47.8 (4)
N5A—C10A—C13A—C14A	−172.6 (3)	N5C—C10C—C13C—C14C	−166.6 (3)
N5A—C10A—C13A—C17A	−55.1 (3)	N5C—C10C—C13C—C17C	−48.9 (4)
C5A—N2A—C4A—N1A	−177.5 (3)	C5C—N2C—C4C—N1C	−179.3 (3)
C5A—N2A—C4A—C3A	−0.8 (5)	C5C—N2C—C4C—C3C	−0.3 (4)
C5A—N3A—C6A—C3A	−2.4 (5)	C5C—N3C—C6C—C3C	2.4 (5)
C5A—N3A—C6A—C7A	174.6 (3)	C5C—N3C—C6C—C7C	−175.2 (3)
C6A—N3A—C5A—N2A	1.0 (6)	C6C—N3C—C5C—N2C	2.8 (6)
C6A—C3A—C4A—N1A	176.7 (3)	C6C—C3C—C4C—N1C	−176.1 (3)
C6A—C3A—C4A—N2A	−0.5 (5)	C6C—C3C—C4C—N2C	4.7 (5)
C6A—C7A—C8A—N4A	−175.6 (3)	C6C—C7C—C8C—N4C	−177.9 (3)
C6A—C7A—C9A—N5A	175.5 (3)	C6C—C7C—C9C—N5C	178.7 (3)
C8A—N4A—N5A—C9A	0.2 (4)	C8C—N4C—N5C—C9C	1.6 (4)
C8A—N4A—N5A—C10A	−173.5 (3)	C8C—N4C—N5C—C10C	179.7 (3)
C8A—C7A—C9A—N5A	0.3 (3)	C8C—C7C—C9C—N5C	1.3 (3)
C9A—N5A—C10A—C11A	57.5 (4)	C9C—N5C—C10C—C11C	60.9 (4)
C9A—N5A—C10A—C13A	−67.0 (4)	C9C—N5C—C10C—C13C	−65.5 (4)
C9A—C7A—C8A—N4A	−0.2 (4)	C9C—C7C—C8C—N4C	−0.4 (4)
C10A—N5A—C9A—C7A	172.7 (3)	C10C—N5C—C9C—C7C	−179.7 (3)
C10A—C13A—C14A—C15A	157.6 (3)	C10C—C13C—C14C—C15C	153.0 (3)
C10A—C13A—C17A—C16A	−164.1 (3)	C10C—C13C—C17C—C16C	−157.6 (4)
C11A—C10A—C13A—C14A	63.6 (4)	C11C—C10C—C13C—C14C	68.0 (4)
C11A—C10A—C13A—C17A	−178.8 (3)	C11C—C10C—C13C—C17C	−174.2 (3)
C13A—C10A—C11A—C12A	172.0 (3)	C13C—C10C—C11C—C12C	174.5 (3)
C13A—C14A—C15A—C16A	−14.5 (5)	C13C—C14C—C15C—C16C	−12.7 (5)
C14A—C13A—C17A—C16A	−39.2 (4)	C14C—C13C—C17C—C16C	−34.7 (5)
C14A—C15A—C16A—C17A	−10.0 (5)	C14C—C15C—C16C—C17C	−8.9 (6)
C15A—C16A—C17A—C13A	31.0 (5)	C15C—C16C—C17C—C13C	27.4 (6)
C17A—C13A—C14A—C15A	32.9 (4)	C17C—C13C—C14C—C15C	29.2 (4)
N1B—C1B—C2B—C3B	−0.8 (4)	N1D—C1D—C2D—C3D	0.4 (5)
C1B—N1B—C4B—N2B	−178.8 (3)	C1D—N1D—C4D—N2D	−178.4 (3)
C1B—N1B—C4B—C3B	−0.3 (4)	C1D—N1D—C4D—C3D	0.8 (4)
C1B—C2B—C3B—C4B	0.6 (4)	C1D—C2D—C3D—C4D	0.1 (4)
C1B—C2B—C3B—C6B	176.2 (4)	C1D—C2D—C3D—C6D	−176.5 (4)
C2B—C3B—C4B—N1B	−0.2 (3)	C2D—C3D—C4D—N1D	−0.5 (4)
C2B—C3B—C4B—N2B	178.4 (3)	C2D—C3D—C4D—N2D	178.7 (3)
C2B—C3B—C6B—N3B	−177.4 (4)	C2D—C3D—C6D—N3D	−178.4 (4)
C2B—C3B—C6B—C7B	−0.4 (6)	C2D—C3D—C6D—C7D	3.5 (6)
N3B—C6B—C7B—C8B	19.7 (5)	N3D—C6D—C7D—C8D	−158.4 (3)
N3B—C6B—C7B—C9B	−164.6 (3)	N3D—C6D—C7D—C9D	17.1 (5)
C3B—C6B—C7B—C8B	−157.3 (3)	C3D—C6D—C7D—C8D	19.6 (5)
C3B—C6B—C7B—C9B	18.4 (5)	C3D—C6D—C7D—C9D	−164.9 (3)
N4B—N5B—C9B—C7B	−0.5 (4)	N4D—N5D—C9D—C7D	1.0 (4)
N4B—N5B—C10B—C11B	66.1 (4)	N4D—N5D—C10D—C11D	57.4 (4)
N4B—N5B—C10B—C13B	−60.1 (4)	N4D—N5D—C10D—C13D	−65.7 (4)
C4B—N1B—C1B—C2B	0.7 (4)	C4D—N1D—C1D—C2D	−0.8 (5)
C4B—N2B—C5B—N3B	−0.3 (6)	C4D—N2D—C5D—N3D	3.6 (5)
C4B—C3B—C6B—N3B	−2.0 (4)	C4D—C3D—C6D—N3D	5.1 (4)
C4B—C3B—C6B—C7B	174.9 (3)	C4D—C3D—C6D—C7D	−172.9 (3)
N5B—N4B—C8B—C7B	0.6 (4)	N5D—N4D—C8D—C7D	1.1 (5)
N5B—C10B—C11B—C12B	53.0 (4)	N5D—C10D—C11D—C12D	52.5 (4)
N5B—C10B—C13B—C14B	−169.6 (3)	N5D—C10D—C13D—C14D	−175.6 (3)
N5B—C10B—C13B—C17B	−52.0 (4)	N5D—C10D—C13D—C17D	−58.4 (3)
C5B—N2B—C4B—N1B	177.9 (3)	C5D—N2D—C4D—N1D	178.7 (3)
C5B—N2B—C4B—C3B	−0.5 (5)	C5D—N2D—C4D—C3D	−0.3 (5)
C5B—N3B—C6B—C3B	1.4 (4)	C5D—N3D—C6D—C3D	−2.5 (5)
C5B—N3B—C6B—C7B	−175.7 (3)	C5D—N3D—C6D—C7D	175.6 (3)
C6B—N3B—C5B—N2B	−0.1 (6)	C6D—N3D—C5D—N2D	−2.3 (6)
C6B—C3B—C4B—N1B	−177.0 (3)	C6D—C3D—C4D—N1D	176.9 (3)
C6B—C3B—C4B—N2B	1.6 (5)	C6D—C3D—C4D—N2D	−3.9 (5)
C6B—C7B—C8B—N4B	175.7 (3)	C6D—C7D—C8D—N4D	175.7 (4)
C6B—C7B—C9B—N5B	−175.8 (3)	C6D—C7D—C9D—N5D	−176.7 (3)
C8B—N4B—N5B—C9B	0.0 (4)	C8D—N4D—N5D—C9D	−1.3 (4)
C8B—N4B—N5B—C10B	175.8 (3)	C8D—N4D—N5D—C10D	177.1 (3)
C8B—C7B—C9B—N5B	0.8 (3)	C8D—C7D—C9D—N5D	−0.2 (4)
C9B—N5B—C10B—C11B	−118.7 (3)	C9D—N5D—C10D—C11D	−124.5 (3)
C9B—N5B—C10B—C13B	115.2 (3)	C9D—N5D—C10D—C13D	112.5 (3)
C9B—C7B—C8B—N4B	−0.9 (4)	C9D—C7D—C8D—N4D	−0.6 (4)
C10B—N5B—C9B—C7B	−176.2 (3)	C10D—N5D—C9D—C7D	−177.2 (3)
C10B—C13B—C14B—C15B	134.5 (5)	C10D—C13D—C14D—C15D	157.6 (3)
C10B—C13B—C17B—C16B	−145.1 (5)	C10D—C13D—C17D—C16D	−157.8 (3)
C11B—C10B—C13B—C14B	65.4 (4)	C11D—C10D—C13D—C14D	61.8 (3)
C11B—C10B—C13B—C17B	−177.1 (3)	C11D—C10D—C13D—C17D	179.0 (3)
C13B—C10B—C11B—C12B	178.7 (3)	C13D—C10D—C11D—C12D	175.5 (3)
C13B—C14B—C15B—C16B	1.3 (8)	C13D—C14D—C15D—C16D	−20.4 (4)
C14B—C13B—C17B—C16B	−23.3 (5)	C14D—C13D—C17D—C16D	−34.7 (4)
C14B—C15B—C16B—C17B	−15.9 (9)	C14D—C15D—C16D—C17D	−1.1 (5)
C15B—C16B—C17B—C13B	24.3 (7)	C15D—C16D—C17D—C13D	22.5 (5)
C17B—C13B—C14B—C15B	12.8 (6)	C17D—C13D—C14D—C15D	33.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N4A^i	0.86	2.08	2.935 (4)	174
N1B—H1B···N4B^ii	0.86	2.12	2.965 (4)	169
N1C—H1C···N2D^iii	0.86	2.09	2.947 (4)	172
N1D—H1D···N2C^iv	0.86	2.14	2.994 (4)	171

Symmetry codes: (i) −x, y−1/2, −z+2; (ii) −x+2, y+1/2, −z+1; (iii) x, y−1, 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)

Crystal data

C17H18N6·2H2O	Dx = 1.274 Mg m^−3
Mr = 342.40	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 9790 reflections
a = 9.9563 (7) Å	θ = 2.9–68.4°
b = 15.1596 (10) Å	µ = 0.72 mm^−1
c = 23.6491 (16) Å	T = 296 K
V = 3569.4 (4) Å^3	Block, colourless
Z = 8	0.47 × 0.28 × 0.23 mm
F(000) = 1456

Data collection

Bruker D8 VENTURE diffractometer	6310 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.054
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 68.6°, θmin = 3.5°
Tmin = 0.512, Tmax = 0.753	h = −12→11
30745 measured reflections	k = −18→18
6516 independent reflections	l = −23→28

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0873P)^2 + 0.4645P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.132	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.35 e Å^−3
6516 reflections	Δρmin = −0.28 e Å^−3
475 parameters	Absolute structure: Flack x determined using 2677 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
8 restraints	Absolute structure parameter: 0.12 (8)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5699 (2)	0.59380 (16)	0.45379 (10)	0.0594 (5)
N1A	0.0605 (3)	0.78564 (16)	0.45821 (10)	0.0542 (6)
H1A	0.064589	0.819748	0.487214	0.065*
C1A	−0.0520 (3)	0.7429 (2)	0.43869 (13)	0.0555 (7)
H1AA	−0.136325	0.746578	0.455458	0.067*
N2A	0.2906 (3)	0.79140 (16)	0.42911 (10)	0.0530 (6)
C2A	−0.0244 (3)	0.69514 (18)	0.39215 (12)	0.0478 (6)
H2A	−0.084519	0.661376	0.371234	0.057*
N3A	0.3408 (2)	0.69824 (16)	0.34967 (10)	0.0491 (5)
C3A	0.1155 (3)	0.70662 (15)	0.38131 (10)	0.0387 (5)
N4A	0.1937 (2)	0.51919 (16)	0.22384 (10)	0.0510 (5)
C4A	0.1633 (3)	0.76444 (16)	0.42367 (11)	0.0448 (6)
N5A	0.0651 (2)	0.54710 (14)	0.22966 (9)	0.0450 (5)
C5A	0.3722 (3)	0.7549 (2)	0.39135 (13)	0.0539 (7)
H5A	0.462250	0.770561	0.394068	0.065*
N6A	−0.0997 (4)	0.3516 (2)	0.28628 (16)	0.0828 (10)
C6A	0.2113 (3)	0.67495 (15)	0.34305 (10)	0.0386 (5)
C7A	0.1760 (3)	0.61685 (16)	0.29573 (11)	0.0404 (5)
C8A	0.0517 (3)	0.60502 (16)	0.27195 (11)	0.0440 (5)
H8A	−0.027542	0.632336	0.283183	0.053*
C9A	0.2612 (3)	0.56179 (18)	0.26402 (11)	0.0468 (6)
H9A	0.352979	0.555915	0.270316	0.056*
C10A	−0.0391 (3)	0.51916 (18)	0.18949 (11)	0.0471 (6)
H10A	−0.125555	0.541096	0.203436	0.057*
C11A	−0.0470 (4)	0.4180 (2)	0.18736 (13)	0.0577 (7)
H11A	−0.116891	0.400647	0.161043	0.069*
H11B	0.037593	0.394802	0.173484	0.069*
C12A	−0.0756 (3)	0.3798 (2)	0.24291 (15)	0.0602 (7)
C13A	−0.0152 (3)	0.55943 (19)	0.13154 (12)	0.0536 (7)
H13A	0.070491	0.537477	0.116779	0.064*
C14A	−0.1259 (4)	0.5395 (2)	0.08832 (14)	0.0693 (9)
H14A	−0.111195	0.482530	0.070644	0.083*
H14B	−0.213471	0.539392	0.106269	0.083*
C15A	−0.1160 (7)	0.6124 (3)	0.0455 (2)	0.1029 (17)
H15A	−0.205068	0.631264	0.034182	0.123*
H15B	−0.068457	0.591890	0.012215	0.123*
C16A	−0.0413 (7)	0.6879 (3)	0.0721 (2)	0.0953 (15)
H16A	−0.095902	0.740942	0.071661	0.114*
H16B	0.041366	0.699510	0.051766	0.114*
C17A	−0.0116 (5)	0.6606 (2)	0.13193 (16)	0.0810 (12)
H17A	−0.078669	0.683958	0.157623	0.097*
H17B	0.076136	0.681708	0.143546	0.097*
N1B	−0.0861 (3)	0.55136 (18)	0.50023 (12)	0.0593 (6)
H1B	−0.131590	0.578815	0.525657	0.071*
C1B	−0.1385 (3)	0.5041 (2)	0.45668 (17)	0.0641 (8)
H1BA	−0.229859	0.497642	0.449686	0.077*
N2B	0.1351 (3)	0.58594 (16)	0.53253 (11)	0.0552 (6)
C2B	−0.0389 (3)	0.4672 (2)	0.42438 (14)	0.0556 (7)
H2B	−0.049210	0.431371	0.392779	0.067*
N3B	0.3094 (2)	0.52576 (16)	0.47437 (10)	0.0498 (5)
C3B	0.0838 (3)	0.49548 (17)	0.44948 (12)	0.0455 (6)
N4B	0.3115 (3)	0.34040 (16)	0.31999 (11)	0.0512 (5)
C4B	0.0494 (3)	0.54800 (18)	0.49692 (12)	0.0505 (6)
N5B	0.4312 (2)	0.36873 (14)	0.34041 (9)	0.0438 (5)
C5B	0.2619 (3)	0.5713 (2)	0.51843 (14)	0.0551 (7)
H5B	0.326080	0.595976	0.542234	0.066*
N6B	0.6053 (6)	0.4695 (3)	0.2061 (2)	0.1141 (15)
C6B	0.2212 (3)	0.48575 (16)	0.43928 (11)	0.0424 (5)
C7B	0.2803 (3)	0.43330 (16)	0.39393 (11)	0.0418 (5)
C8B	0.4161 (3)	0.42347 (17)	0.38433 (12)	0.0453 (6)
H8B	0.484907	0.450116	0.404730	0.054*
C9B	0.2206 (3)	0.38016 (19)	0.35224 (12)	0.0497 (6)
H9B	0.128350	0.373612	0.347755	0.060*
C10B	0.5602 (3)	0.33106 (19)	0.32143 (12)	0.0499 (6)
H10B	0.630327	0.373599	0.331480	0.060*
C11B	0.5622 (3)	0.3219 (2)	0.25717 (12)	0.0562 (7)
H11C	0.633146	0.281272	0.246518	0.067*
H11D	0.477552	0.296852	0.244722	0.067*
C12B	0.5835 (4)	0.4055 (3)	0.22855 (16)	0.0690 (9)
C13B	0.5960 (4)	0.2444 (2)	0.35023 (15)	0.0651 (9)
H13B	0.679680	0.224025	0.332728	0.078*
C14B	0.6238 (6)	0.2519 (3)	0.41325 (19)	0.0926 (14)
H14C	0.560909	0.291909	0.431241	0.111*
H14D	0.714568	0.272495	0.420190	0.111*
C15B	0.6050 (10)	0.1578 (4)	0.4347 (2)	0.127 (3)
H15C	0.691129	0.132678	0.444960	0.152*
H15D	0.547828	0.157792	0.467906	0.152*
C16B	0.5441 (9)	0.1065 (4)	0.3904 (3)	0.127 (2)
H16C	0.467916	0.073730	0.404988	0.152*
H16D	0.608450	0.064970	0.374925	0.152*
H1C	0.585 (10)	0.601 (6)	0.4179 (11)	0.190*
H1D	0.487 (3)	0.577 (6)	0.453 (4)	0.190*
H2C	0.523 (6)	0.642 (5)	0.336 (4)	0.190*
H2D	0.649 (8)	0.623 (7)	0.311 (3)	0.190*
H3A	0.278 (10)	0.424 (3)	0.167 (4)	0.190*
H3B	0.315 (10)	0.382 (6)	0.1182 (14)	0.190*
H4A	0.245 (11)	0.242 (6)	0.2576 (14)	0.190*
H4B	0.242 (11)	0.262 (5)	0.193 (2)	0.190*
C17B	0.4986 (5)	0.1708 (3)	0.3450 (2)	0.0823 (11)
H17C	0.502917	0.144157	0.307782	0.099*
H17D	0.407616	0.190965	0.351983	0.099*
O2	0.5916 (3)	0.6060 (2)	0.33650 (13)	0.0809 (7)
O3	0.2935 (3)	0.37210 (17)	0.15329 (12)	0.0755 (7)
O4	0.2324 (3)	0.22662 (18)	0.22250 (11)	0.0708 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0533 (11)	0.0670 (12)	0.0578 (12)	0.0018 (10)	−0.0007 (10)	−0.0181 (10)
N1A	0.0692 (15)	0.0509 (12)	0.0425 (12)	0.0057 (11)	0.0025 (11)	−0.0102 (10)
C1A	0.0571 (17)	0.0550 (15)	0.0544 (16)	0.0050 (13)	0.0088 (13)	−0.0021 (12)
N2A	0.0598 (14)	0.0520 (12)	0.0472 (12)	−0.0052 (11)	−0.0109 (11)	−0.0079 (10)
C2A	0.0502 (14)	0.0461 (13)	0.0471 (14)	−0.0016 (11)	0.0017 (11)	−0.0022 (11)
N3A	0.0474 (12)	0.0550 (12)	0.0450 (12)	−0.0060 (10)	0.0003 (10)	−0.0013 (10)
C3A	0.0471 (13)	0.0347 (10)	0.0344 (11)	0.0009 (9)	−0.0033 (9)	0.0015 (9)
N4A	0.0526 (13)	0.0519 (12)	0.0483 (12)	0.0090 (10)	−0.0025 (10)	−0.0146 (10)
C4A	0.0615 (16)	0.0373 (11)	0.0354 (12)	0.0024 (11)	−0.0033 (11)	−0.0006 (10)
N5A	0.0495 (12)	0.0446 (10)	0.0410 (11)	0.0017 (9)	−0.0033 (10)	−0.0095 (8)
C5A	0.0499 (15)	0.0598 (16)	0.0520 (16)	−0.0085 (13)	−0.0085 (13)	−0.0057 (13)
N6A	0.077 (2)	0.085 (2)	0.086 (2)	−0.0132 (17)	−0.0124 (17)	0.0258 (18)
C6A	0.0456 (13)	0.0369 (10)	0.0331 (11)	−0.0004 (9)	−0.0017 (10)	0.0026 (9)
C7A	0.0471 (13)	0.0386 (11)	0.0355 (11)	0.0008 (10)	−0.0016 (10)	−0.0007 (9)
C8A	0.0480 (13)	0.0432 (12)	0.0409 (13)	0.0017 (10)	−0.0007 (11)	−0.0064 (10)
C9A	0.0444 (13)	0.0518 (13)	0.0442 (13)	0.0034 (11)	−0.0021 (11)	−0.0065 (11)
C10A	0.0492 (14)	0.0482 (13)	0.0440 (14)	−0.0018 (11)	−0.0052 (11)	−0.0106 (11)
C11A	0.0677 (19)	0.0490 (14)	0.0564 (17)	−0.0076 (13)	−0.0068 (14)	−0.0092 (12)
C12A	0.0570 (17)	0.0549 (15)	0.069 (2)	−0.0071 (14)	−0.0128 (15)	0.0014 (14)
C13A	0.0605 (17)	0.0540 (15)	0.0462 (14)	−0.0039 (13)	−0.0061 (13)	−0.0071 (12)
C14A	0.085 (2)	0.0686 (19)	0.0539 (18)	−0.0127 (17)	−0.0199 (16)	−0.0077 (15)
C15A	0.144 (5)	0.093 (3)	0.072 (3)	−0.021 (3)	−0.043 (3)	0.015 (2)
C16A	0.138 (4)	0.071 (2)	0.077 (3)	−0.014 (3)	−0.024 (3)	0.0106 (19)
C17A	0.123 (4)	0.0581 (18)	0.062 (2)	−0.017 (2)	−0.021 (2)	−0.0015 (15)
N1B	0.0559 (14)	0.0574 (13)	0.0646 (15)	0.0095 (12)	0.0218 (12)	0.0021 (12)
C1B	0.0439 (15)	0.0646 (18)	0.084 (2)	0.0061 (13)	0.0107 (15)	0.0088 (17)
N2B	0.0638 (15)	0.0505 (12)	0.0513 (13)	0.0041 (11)	0.0127 (12)	−0.0059 (11)
C2B	0.0477 (14)	0.0537 (14)	0.0654 (18)	0.0017 (12)	0.0046 (13)	−0.0004 (13)
N3B	0.0503 (13)	0.0503 (12)	0.0487 (12)	−0.0015 (10)	0.0072 (10)	−0.0082 (10)
C3B	0.0479 (14)	0.0408 (11)	0.0478 (14)	0.0064 (10)	0.0070 (11)	0.0033 (10)
N4B	0.0515 (13)	0.0531 (12)	0.0491 (12)	0.0027 (10)	−0.0025 (10)	−0.0097 (11)
C4B	0.0580 (16)	0.0438 (13)	0.0498 (15)	0.0073 (12)	0.0166 (13)	0.0059 (11)
N5B	0.0458 (11)	0.0436 (10)	0.0419 (11)	0.0008 (9)	0.0033 (9)	−0.0063 (8)
C5B	0.0605 (17)	0.0527 (15)	0.0521 (15)	−0.0033 (13)	0.0074 (13)	−0.0089 (12)
N6B	0.127 (4)	0.107 (3)	0.108 (3)	0.004 (3)	0.010 (3)	0.040 (3)
C6B	0.0468 (13)	0.0386 (11)	0.0419 (12)	0.0021 (10)	0.0067 (10)	0.0011 (10)
C7B	0.0457 (13)	0.0385 (11)	0.0412 (12)	0.0015 (10)	0.0037 (10)	0.0011 (10)
C8B	0.0466 (13)	0.0434 (12)	0.0460 (13)	0.0010 (10)	0.0033 (11)	−0.0095 (10)
C9B	0.0474 (14)	0.0541 (14)	0.0477 (14)	0.0029 (11)	0.0004 (11)	−0.0055 (12)
C10B	0.0504 (15)	0.0508 (14)	0.0485 (14)	0.0076 (12)	0.0031 (12)	−0.0088 (11)
C11B	0.0541 (16)	0.0665 (17)	0.0481 (15)	−0.0003 (13)	0.0099 (13)	−0.0120 (13)
C12B	0.0618 (19)	0.084 (2)	0.0613 (19)	0.0061 (17)	0.0055 (16)	0.0075 (18)
C13B	0.078 (2)	0.0549 (16)	0.0626 (18)	0.0217 (16)	0.0004 (16)	−0.0078 (14)
C14B	0.127 (4)	0.078 (2)	0.073 (3)	0.024 (3)	−0.020 (3)	−0.003 (2)
C15B	0.211 (8)	0.089 (3)	0.081 (3)	0.020 (4)	−0.019 (4)	0.022 (3)
C16B	0.158 (6)	0.080 (3)	0.143 (5)	−0.005 (4)	−0.026 (5)	0.033 (3)
C17B	0.092 (3)	0.0642 (19)	0.090 (3)	0.004 (2)	−0.011 (2)	0.0018 (19)
O2	0.0754 (17)	0.0926 (18)	0.0748 (17)	0.0053 (15)	0.0128 (13)	0.0057 (14)
O3	0.100 (2)	0.0619 (13)	0.0648 (14)	0.0008 (13)	0.0096 (14)	−0.0053 (11)
O4	0.0682 (15)	0.0779 (15)	0.0664 (14)	−0.0123 (12)	−0.0035 (12)	−0.0112 (12)

Geometric parameters (Å, º)

O1—H1C	0.868 (14)	N1B—C4B	1.352 (4)
O1—H1D	0.863 (14)	C1B—H1BA	0.9300
N1A—H1A	0.8600	C1B—C2B	1.371 (5)
N1A—C1A	1.373 (4)	N2B—C4B	1.330 (4)
N1A—C4A	1.349 (4)	N2B—C5B	1.324 (4)
C1A—H1AA	0.9300	C2B—H2B	0.9300
C1A—C2A	1.346 (4)	C2B—C3B	1.424 (4)
N2A—C4A	1.337 (4)	N3B—C5B	1.337 (4)
N2A—C5A	1.328 (4)	N3B—C6B	1.352 (4)
C2A—H2A	0.9300	C3B—C4B	1.418 (4)
C2A—C3A	1.427 (4)	C3B—C6B	1.396 (4)
N3A—C5A	1.345 (4)	N4B—N5B	1.356 (3)
N3A—C6A	1.346 (4)	N4B—C9B	1.328 (4)
C3A—C4A	1.414 (4)	N5B—C8B	1.338 (3)
C3A—C6A	1.400 (4)	N5B—C10B	1.475 (4)
N4A—N5A	1.355 (3)	C5B—H5B	0.9300
N4A—C9A	1.331 (4)	N6B—C12B	1.128 (6)
N5A—C8A	1.337 (3)	C6B—C7B	1.459 (3)
N5A—C10A	1.469 (3)	C7B—C8B	1.379 (4)
C5A—H5A	0.9300	C7B—C9B	1.405 (4)
N6A—C12A	1.137 (5)	C8B—H8B	0.9300
C6A—C7A	1.467 (3)	C9B—H9B	0.9300
C7A—C8A	1.371 (4)	C10B—H10B	0.9800
C7A—C9A	1.407 (4)	C10B—C11B	1.526 (4)
C8A—H8A	0.9300	C10B—C13B	1.522 (4)
C9A—H9A	0.9300	C11B—H11C	0.9700
C10A—H10A	0.9800	C11B—H11D	0.9700
C10A—C11A	1.536 (4)	C11B—C12B	1.453 (5)
C10A—C13A	1.519 (4)	C13B—H13B	0.9800
C11A—H11A	0.9700	C13B—C14B	1.520 (6)
C11A—H11B	0.9700	C13B—C17B	1.484 (6)
C11A—C12A	1.464 (5)	C14B—H14C	0.9700
C13A—H13A	0.9800	C14B—H14D	0.9700
C13A—C14A	1.533 (4)	C14B—C15B	1.525 (7)
C13A—C17A	1.534 (4)	C15B—H15C	0.9700
C14A—H14A	0.9700	C15B—H15D	0.9700
C14A—H14B	0.9700	C15B—C16B	1.439 (9)
C14A—C15A	1.502 (6)	C16B—H16C	0.9700
C15A—H15A	0.9700	C16B—H16D	0.9700
C15A—H15B	0.9700	C16B—C17B	1.519 (7)
C15A—C16A	1.503 (7)	C17B—H17C	0.9700
C16A—H16A	0.9700	C17B—H17D	0.9700
C16A—H16B	0.9700	O2—H2C	0.878 (14)
C16A—C17A	1.503 (6)	O2—H2D	0.872 (14)
C17A—H17A	0.9700	O3—H3A	0.867 (14)
C17A—H17B	0.9700	O3—H3B	0.870 (14)
N1B—H1B	0.8600	O4—H4A	0.872 (14)
N1B—C1B	1.358 (5)	O4—H4B	0.877 (14)
H1C—O1—H1D	100 (8)	C4B—N1B—H1B	125.7
C1A—N1A—H1A	126.2	C4B—N1B—C1B	108.6 (3)
C4A—N1A—H1A	126.2	N1B—C1B—H1BA	124.5
C4A—N1A—C1A	107.7 (2)	N1B—C1B—C2B	111.1 (3)
N1A—C1A—H1AA	124.4	C2B—C1B—H1BA	124.5
C2A—C1A—N1A	111.2 (3)	C5B—N2B—C4B	112.4 (2)
C2A—C1A—H1AA	124.4	C1B—C2B—H2B	127.3
C5A—N2A—C4A	112.8 (2)	C1B—C2B—C3B	105.4 (3)
C1A—C2A—H2A	126.9	C3B—C2B—H2B	127.3
C1A—C2A—C3A	106.3 (3)	C5B—N3B—C6B	118.7 (3)
C3A—C2A—H2A	126.9	C4B—C3B—C2B	106.9 (3)
C5A—N3A—C6A	118.4 (3)	C6B—C3B—C2B	137.4 (3)
C4A—C3A—C2A	106.1 (2)	C6B—C3B—C4B	115.7 (3)
C6A—C3A—C2A	137.7 (2)	C9B—N4B—N5B	104.5 (2)
C6A—C3A—C4A	116.2 (2)	N1B—C4B—C3B	108.0 (3)
C9A—N4A—N5A	104.7 (2)	N2B—C4B—N1B	126.0 (3)
N1A—C4A—C3A	108.7 (2)	N2B—C4B—C3B	126.0 (3)
N2A—C4A—N1A	126.0 (2)	N4B—N5B—C10B	122.3 (2)
N2A—C4A—C3A	125.2 (3)	C8B—N5B—N4B	112.0 (2)
N4A—N5A—C10A	120.8 (2)	C8B—N5B—C10B	125.0 (2)
C8A—N5A—N4A	112.0 (2)	N2B—C5B—N3B	128.3 (3)
C8A—N5A—C10A	127.0 (2)	N2B—C5B—H5B	115.8
N2A—C5A—N3A	128.1 (3)	N3B—C5B—H5B	115.8
N2A—C5A—H5A	116.0	N3B—C6B—C3B	118.9 (2)
N3A—C5A—H5A	116.0	N3B—C6B—C7B	115.7 (2)
N3A—C6A—C3A	119.2 (2)	C3B—C6B—C7B	125.4 (2)
N3A—C6A—C7A	118.4 (2)	C8B—C7B—C6B	125.1 (2)
C3A—C6A—C7A	122.4 (2)	C8B—C7B—C9B	103.7 (2)
C8A—C7A—C6A	127.4 (2)	C9B—C7B—C6B	131.1 (3)
C8A—C7A—C9A	104.4 (2)	N5B—C8B—C7B	107.7 (2)
C9A—C7A—C6A	128.2 (2)	N5B—C8B—H8B	126.1
N5A—C8A—C7A	107.6 (2)	C7B—C8B—H8B	126.1
N5A—C8A—H8A	126.2	N4B—C9B—C7B	112.0 (3)
C7A—C8A—H8A	126.2	N4B—C9B—H9B	124.0
N4A—C9A—C7A	111.3 (2)	C7B—C9B—H9B	124.0
N4A—C9A—H9A	124.3	N5B—C10B—H10B	107.0
C7A—C9A—H9A	124.3	N5B—C10B—C11B	110.5 (2)
N5A—C10A—H10A	107.7	N5B—C10B—C13B	113.7 (3)
N5A—C10A—C11A	110.2 (2)	C11B—C10B—H10B	107.0
N5A—C10A—C13A	110.9 (2)	C13B—C10B—H10B	107.0
C11A—C10A—H10A	107.7	C13B—C10B—C11B	111.3 (2)
C13A—C10A—H10A	107.7	C10B—C11B—H11C	109.0
C13A—C10A—C11A	112.3 (2)	C10B—C11B—H11D	109.0
C10A—C11A—H11A	109.2	H11C—C11B—H11D	107.8
C10A—C11A—H11B	109.2	C12B—C11B—C10B	112.7 (3)
H11A—C11A—H11B	107.9	C12B—C11B—H11C	109.0
C12A—C11A—C10A	112.1 (3)	C12B—C11B—H11D	109.0
C12A—C11A—H11A	109.2	N6B—C12B—C11B	177.2 (5)
C12A—C11A—H11B	109.2	C10B—C13B—H13B	106.4
N6A—C12A—C11A	178.5 (4)	C14B—C13B—C10B	114.7 (3)
C10A—C13A—H13A	108.7	C14B—C13B—H13B	106.4
C10A—C13A—C14A	114.2 (3)	C17B—C13B—C10B	117.3 (3)
C10A—C13A—C17A	113.6 (3)	C17B—C13B—H13B	106.4
C14A—C13A—H13A	108.7	C17B—C13B—C14B	104.9 (4)
C14A—C13A—C17A	102.6 (3)	C13B—C14B—H14C	111.1
C17A—C13A—H13A	108.7	C13B—C14B—H14D	111.1
C13A—C14A—H14A	110.8	C13B—C14B—C15B	103.5 (4)
C13A—C14A—H14B	110.8	H14C—C14B—H14D	109.0
H14A—C14A—H14B	108.8	C15B—C14B—H14C	111.1
C15A—C14A—C13A	104.9 (3)	C15B—C14B—H14D	111.1
C15A—C14A—H14A	110.8	C14B—C15B—H15C	110.0
C15A—C14A—H14B	110.8	C14B—C15B—H15D	110.0
C14A—C15A—H15A	110.1	H15C—C15B—H15D	108.4
C14A—C15A—H15B	110.1	C16B—C15B—C14B	108.4 (4)
C14A—C15A—C16A	108.1 (3)	C16B—C15B—H15C	110.0
H15A—C15A—H15B	108.4	C16B—C15B—H15D	110.0
C16A—C15A—H15A	110.1	C15B—C16B—H16C	110.3
C16A—C15A—H15B	110.1	C15B—C16B—H16D	110.3
C15A—C16A—H16A	110.5	C15B—C16B—C17B	107.0 (4)
C15A—C16A—H16B	110.5	H16C—C16B—H16D	108.6
C15A—C16A—C17A	106.3 (4)	C17B—C16B—H16C	110.3
H16A—C16A—H16B	108.7	C17B—C16B—H16D	110.3
C17A—C16A—H16A	110.5	C13B—C17B—C16B	103.3 (4)
C17A—C16A—H16B	110.5	C13B—C17B—H17C	111.1
C13A—C17A—H17A	110.7	C13B—C17B—H17D	111.1
C13A—C17A—H17B	110.7	C16B—C17B—H17C	111.1
C16A—C17A—C13A	105.4 (3)	C16B—C17B—H17D	111.1
C16A—C17A—H17A	110.7	H17C—C17B—H17D	109.1
C16A—C17A—H17B	110.7	H2C—O2—H2D	109 (8)
H17A—C17A—H17B	108.8	H3A—O3—H3B	104 (8)
C1B—N1B—H1B	125.7	H4A—O4—H4B	125 (8)
N1A—C1A—C2A—C3A	0.9 (3)	N1B—C1B—C2B—C3B	−1.2 (4)
C1A—N1A—C4A—N2A	−178.6 (3)	C1B—N1B—C4B—N2B	−179.5 (3)
C1A—N1A—C4A—C3A	−0.2 (3)	C1B—N1B—C4B—C3B	−0.6 (3)
C1A—C2A—C3A—C4A	−1.0 (3)	C1B—C2B—C3B—C4B	0.7 (3)
C1A—C2A—C3A—C6A	176.5 (3)	C1B—C2B—C3B—C6B	−178.4 (3)
C2A—C3A—C4A—N1A	0.8 (3)	C2B—C3B—C4B—N1B	−0.1 (3)
C2A—C3A—C4A—N2A	179.1 (3)	C2B—C3B—C4B—N2B	178.8 (3)
C2A—C3A—C6A—N3A	−175.1 (3)	C2B—C3B—C6B—N3B	179.2 (3)
C2A—C3A—C6A—C7A	4.8 (4)	C2B—C3B—C6B—C7B	−2.4 (5)
N3A—C6A—C7A—C8A	−160.3 (3)	N3B—C6B—C7B—C8B	−1.1 (4)
N3A—C6A—C7A—C9A	18.8 (4)	N3B—C6B—C7B—C9B	176.4 (3)
C3A—C6A—C7A—C8A	19.8 (4)	C3B—C6B—C7B—C8B	−179.5 (3)
C3A—C6A—C7A—C9A	−161.1 (3)	C3B—C6B—C7B—C9B	−2.0 (4)
N4A—N5A—C8A—C7A	0.0 (3)	N4B—N5B—C8B—C7B	−0.5 (3)
N4A—N5A—C10A—C11A	56.7 (3)	N4B—N5B—C10B—C11B	45.1 (4)
N4A—N5A—C10A—C13A	−68.3 (3)	N4B—N5B—C10B—C13B	−80.9 (3)
C4A—N1A—C1A—C2A	−0.4 (3)	C4B—N1B—C1B—C2B	1.2 (4)
C4A—N2A—C5A—N3A	1.6 (5)	C4B—N2B—C5B—N3B	0.6 (5)
C4A—C3A—C6A—N3A	2.2 (3)	C4B—C3B—C6B—N3B	0.1 (4)
C4A—C3A—C6A—C7A	−177.9 (2)	C4B—C3B—C6B—C7B	178.5 (2)
N5A—N4A—C9A—C7A	0.2 (3)	N5B—N4B—C9B—C7B	−0.7 (3)
N5A—C10A—C11A—C12A	58.2 (4)	N5B—C10B—C11B—C12B	76.3 (3)
N5A—C10A—C13A—C14A	−175.4 (3)	N5B—C10B—C13B—C14B	−66.1 (5)
N5A—C10A—C13A—C17A	−58.2 (4)	N5B—C10B—C13B—C17B	57.5 (4)
C5A—N2A—C4A—N1A	175.3 (3)	C5B—N2B—C4B—N1B	−179.9 (3)
C5A—N2A—C4A—C3A	−2.7 (4)	C5B—N2B—C4B—C3B	1.5 (4)
C5A—N3A—C6A—C3A	−3.3 (4)	C5B—N3B—C6B—C3B	1.7 (4)
C5A—N3A—C6A—C7A	176.8 (2)	C5B—N3B—C6B—C7B	−176.8 (3)
C6A—N3A—C5A—N2A	1.5 (5)	C6B—N3B—C5B—N2B	−2.3 (5)
C6A—C3A—C4A—N1A	−177.4 (2)	C6B—C3B—C4B—N1B	179.3 (2)
C6A—C3A—C4A—N2A	1.0 (4)	C6B—C3B—C4B—N2B	−1.9 (4)
C6A—C7A—C8A—N5A	179.3 (2)	C6B—C7B—C8B—N5B	178.1 (2)
C6A—C7A—C9A—N4A	−179.4 (2)	C6B—C7B—C9B—N4B	−177.5 (3)
C8A—N5A—C10A—C11A	−128.5 (3)	C8B—N5B—C10B—C11B	−145.3 (3)
C8A—N5A—C10A—C13A	106.5 (3)	C8B—N5B—C10B—C13B	88.7 (3)
C8A—C7A—C9A—N4A	−0.2 (3)	C8B—C7B—C9B—N4B	0.5 (3)
C9A—N4A—N5A—C8A	−0.1 (3)	C9B—N4B—N5B—C8B	0.7 (3)
C9A—N4A—N5A—C10A	175.4 (2)	C9B—N4B—N5B—C10B	171.6 (3)
C9A—C7A—C8A—N5A	0.1 (3)	C9B—C7B—C8B—N5B	0.0 (3)
C10A—N5A—C8A—C7A	−175.2 (3)	C10B—N5B—C8B—C7B	−171.0 (2)
C10A—C13A—C14A—C15A	156.5 (4)	C10B—C13B—C14B—C15B	159.8 (5)
C10A—C13A—C17A—C16A	−158.6 (4)	C10B—C13B—C17B—C16B	−164.8 (4)
C11A—C10A—C13A—C14A	60.8 (4)	C11B—C10B—C13B—C14B	168.3 (4)
C11A—C10A—C13A—C17A	178.0 (3)	C11B—C10B—C13B—C17B	−68.1 (4)
C13A—C10A—C11A—C12A	−177.6 (3)	C13B—C10B—C11B—C12B	−156.3 (3)
C13A—C14A—C15A—C16A	−19.7 (6)	C13B—C14B—C15B—C16B	−11.3 (8)
C14A—C13A—C17A—C16A	−34.8 (5)	C14B—C13B—C17B—C16B	−36.4 (5)
C14A—C15A—C16A—C17A	−2.1 (7)	C14B—C15B—C16B—C17B	−11.0 (9)
C15A—C16A—C17A—C13A	23.2 (6)	C15B—C16B—C17B—C13B	29.5 (8)
C17A—C13A—C14A—C15A	33.2 (5)	C17B—C13B—C14B—C15B	29.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1^i	0.86	1.91	2.771 (3)	174
O1—H1C···O2	0.87 (1)	1.93 (2)	2.788 (4)	171 (10)
O1—H1D···N3B	0.86 (1)	2.00 (3)	2.833 (3)	162 (9)
O2—H2C···N3A	0.88 (1)	2.03 (3)	2.879 (4)	163 (9)
O2—H2D···O4^ii	0.87 (1)	2.12 (6)	2.892 (4)	147 (9)
O3—H3A···N4A	0.87 (1)	2.14 (4)	2.957 (3)	157 (9)
O3—H3B···N2B^iii	0.87 (1)	2.14 (2)	3.011 (4)	177 (9)
O4—H4A···N4B	0.87 (1)	2.20 (5)	2.985 (3)	150 (9)
O4—H4B···O3	0.88 (1)	1.99 (4)	2.813 (4)	156 (8)

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1/2, −y+1, z−1/2.

4-{1-[(1R)-2-Cyano-1-cyclopentylethyl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-3-ium dihydrogen phosphate (rux-p)

Crystal data

C17H19N6^+·H2PO4^−	Dx = 1.420 Mg m^−3
Mr = 404.37	Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, P212121	Cell parameters from 9334 reflections
a = 7.1398 (4) Å	θ = 3.3–55.5°
b = 12.0894 (6) Å	µ = 1.05 mm^−1
c = 43.818 (2) Å	T = 296 K
V = 3782.2 (4) Å^3	Needle, colourless
Z = 8	0.11 × 0.04 × 0.02 mm
F(000) = 1696

Data collection

Bruker D8 VENTURE diffractometer	6947 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.063
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 60.5°, θmin = 3.3°
Tmin = 0.612, Tmax = 0.752	h = −9→9
84024 measured reflections	k = −13→15
8662 independent reflections	l = −56→56

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0717P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.18 e Å^−3
8662 reflections	Δρmin = −0.31 e Å^−3
559 parameters	Absolute structure: Flack x determined using 2547 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
191 restraints	Absolute structure parameter: 0.044 (8)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1A	0.65649 (11)	0.45547 (6)	0.42726 (2)	0.04229 (19)
O1A	0.6066 (3)	0.54089 (16)	0.40388 (5)	0.0514 (5)
O2A	0.5943 (4)	0.48670 (18)	0.45935 (5)	0.0560 (6)
O3A	0.5760 (4)	0.34235 (18)	0.41825 (5)	0.0548 (6)
H3AA	0.494 (4)	0.317 (3)	0.4296 (8)	0.082*
O4A	0.8722 (3)	0.4475 (2)	0.42736 (7)	0.0727 (8)
H4A	0.905636	0.402615	0.440290	0.109*
P1B	0.21366 (10)	0.30897 (6)	0.47465 (2)	0.03782 (17)
O1B	0.3300 (3)	0.24909 (15)	0.45067 (4)	0.0449 (5)
O2B	0.2951 (3)	0.42237 (17)	0.48157 (5)	0.0519 (5)
H2BA	0.381 (4)	0.449 (3)	0.4712 (8)	0.078*
O3B	0.0103 (3)	0.31624 (19)	0.46592 (5)	0.0537 (5)
O4B	0.2128 (3)	0.2396 (2)	0.50465 (5)	0.0537 (5)
H4B	0.319855	0.219606	0.508604	0.081*
N1A	0.8069 (4)	1.03408 (19)	0.45525 (6)	0.0470 (6)
H1A	0.828444	1.054736	0.473701	0.056*
C1A	0.7998 (5)	1.1024 (2)	0.43002 (7)	0.0514 (7)
H1AA	0.815717	1.178725	0.430489	0.062*
N2A	0.7629 (4)	0.84118 (19)	0.46466 (5)	0.0467 (6)
C2A	0.7663 (5)	1.0423 (2)	0.40451 (7)	0.0472 (7)
H2A	0.756075	1.069027	0.384669	0.057*
N3A	0.6946 (3)	0.73956 (18)	0.41971 (5)	0.0418 (5)
H3A	0.666753	0.675849	0.412256	0.050*
C3A	0.7499 (4)	0.9295 (2)	0.41416 (6)	0.0388 (6)
N4A	0.5699 (5)	0.7373 (2)	0.32401 (6)	0.0634 (8)
C4A	0.7743 (4)	0.9295 (2)	0.44602 (6)	0.0408 (6)
N5A	0.6691 (4)	0.8315 (2)	0.31873 (5)	0.0501 (6)
C5A	0.7229 (5)	0.7489 (2)	0.44995 (6)	0.0461 (7)
H5A	0.713479	0.684635	0.461509	0.055*
N6A	0.4936 (9)	0.9492 (4)	0.21840 (9)	0.1197 (19)
C6A	0.7086 (4)	0.8276 (2)	0.40058 (6)	0.0380 (6)
C7A	0.6785 (4)	0.8103 (2)	0.36838 (6)	0.0413 (6)
C8A	0.5788 (5)	0.7231 (3)	0.35413 (7)	0.0566 (9)
H8A	0.526349	0.663526	0.364482	0.068*
C9A	0.7336 (5)	0.8773 (2)	0.34439 (6)	0.0447 (6)
H9A	0.802701	0.942331	0.345869	0.054*
C10A	0.6929 (5)	0.8715 (3)	0.28734 (7)	0.0527 (8)
H10C	0.750266	0.944981	0.288622	0.063*
C11A	0.4956 (6)	0.8873 (4)	0.27458 (8)	0.0668 (10)
H11C	0.428013	0.817890	0.276149	0.080*
H11D	0.430106	0.941503	0.286912	0.080*
C12A	0.4943 (7)	0.9235 (4)	0.24290 (9)	0.0769 (12)
C13A	0.8203 (6)	0.8007 (3)	0.26771 (8)	0.0653 (9)
H13A	0.844244	0.842837	0.249014	0.078*
C14A	0.7510 (7)	0.6881 (4)	0.25778 (11)	0.0862 (13)
H14C	0.671000	0.694403	0.239972	0.103*
H14D	0.681059	0.652733	0.274053	0.103*
C15A	0.9283 (10)	0.6222 (5)	0.25026 (16)	0.123 (2)
H15C	0.921848	0.549309	0.259430	0.148*
H15D	0.940692	0.613606	0.228343	0.148*
C16A	1.0900 (9)	0.6840 (6)	0.26258 (15)	0.121 (2)
H16C	1.165174	0.713739	0.246072	0.145*
H16D	1.168081	0.635634	0.274843	0.145*
C17A	1.0113 (6)	0.7771 (4)	0.28205 (12)	0.0894 (13)
H17C	1.091281	0.841934	0.281168	0.107*
H17D	0.998183	0.754196	0.303150	0.107*
N1B	0.2387 (4)	−0.2951 (2)	0.46540 (7)	0.0579 (7)
H1B	0.245886	−0.333642	0.481847	0.069*
C1B	0.1951 (5)	−0.3349 (3)	0.43719 (9)	0.0613 (9)
H1BA	0.169441	−0.408612	0.432853	0.074*
N2B	0.3140 (5)	−0.1196 (2)	0.48662 (6)	0.0565 (7)
C2B	0.1944 (5)	−0.2521 (3)	0.41632 (8)	0.0538 (8)
H2B	0.166616	−0.258422	0.395658	0.065*
N3B	0.3096 (4)	0.02370 (18)	0.45001 (5)	0.0437 (6)
H3B	0.323506	0.093495	0.446977	0.052*
C3B	0.2446 (4)	−0.1535 (2)	0.43224 (7)	0.0436 (6)
N4B	0.2251 (6)	0.0366 (3)	0.34516 (6)	0.0733 (9)
C4B	0.2688 (4)	−0.1855 (2)	0.46329 (7)	0.0466 (7)
N5B	0.2470 (5)	0.1350 (2)	0.35969 (6)	0.0584 (7)
C5B	0.3305 (6)	−0.0154 (3)	0.47894 (7)	0.0550 (8)
H5B	0.358336	0.035204	0.494261	0.066*
N6B	0.6761 (8)	0.1284 (4)	0.31372 (12)	0.1215 (18)
C6B	0.2678 (4)	−0.0417 (2)	0.42557 (6)	0.0400 (6)
C7B	0.2549 (4)	0.0101 (2)	0.39595 (6)	0.0417 (6)
C8B	0.2285 (6)	−0.0375 (3)	0.36689 (8)	0.0632 (9)
H8B	0.215123	−0.113032	0.363552	0.076*
C9B	0.2651 (5)	0.1216 (3)	0.38945 (7)	0.0516 (8)
H9B	0.281796	0.177880	0.403652	0.062*
C10B	0.2655 (7)	0.2388 (4)	0.34224 (9)	0.0811 (13)
H10A	0.242871	0.214219	0.321251	0.097*	0.388 (6)
H10B	0.216155	0.229527	0.321530	0.097*	0.612 (6)
C11B	0.4702 (8)	0.2727 (3)	0.34127 (10)	0.0904 (16)
H11A	0.481001	0.343220	0.330875	0.109*
H11B	0.515437	0.282391	0.361971	0.109*
C12B	0.5875 (8)	0.1917 (4)	0.32576 (10)	0.0865 (14)
C13B	0.1702 (13)	0.3396 (5)	0.35836 (18)	0.0632 (19)	0.612 (6)
H13B	0.204885	0.340211	0.379996	0.076*	0.612 (6)
C14B	0.2067 (12)	0.4547 (5)	0.34448 (19)	0.084 (2)	0.612 (6)
H14A	0.308344	0.491948	0.354978	0.101*	0.612 (6)
H14B	0.237082	0.449126	0.322961	0.101*	0.612 (6)
C15B	0.0201 (19)	0.5161 (9)	0.3493 (3)	0.103 (4)	0.612 (6)
H15A	0.009438	0.543545	0.369986	0.124*	0.612 (6)
H15B	0.008035	0.577597	0.335172	0.124*	0.612 (6)
C16B	−0.1270 (15)	0.4270 (9)	0.3428 (3)	0.105 (3)	0.612 (6)
H16A	−0.244098	0.444324	0.352922	0.126*	0.612 (6)
H16B	−0.149808	0.420502	0.321028	0.126*	0.612 (6)
C17B	−0.0436 (12)	0.3207 (6)	0.35536 (18)	0.082 (2)	0.612 (6)
H17A	−0.068729	0.259543	0.341642	0.098*	0.612 (6)
H17B	−0.097603	0.303747	0.375127	0.098*	0.612 (6)
C18	0.091 (2)	0.3083 (10)	0.3490 (3)	0.066 (3)	0.388 (6)
H18	−0.011064	0.261066	0.356444	0.079*	0.388 (6)
C19	0.1496 (19)	0.3913 (11)	0.3738 (3)	0.088 (3)	0.388 (6)
H19A	0.284235	0.389665	0.376746	0.105*	0.388 (6)
H19B	0.089260	0.373878	0.393055	0.105*	0.388 (6)
C20	0.086 (3)	0.5074 (13)	0.3621 (4)	0.104 (5)	0.388 (6)
H20A	0.024612	0.548628	0.378297	0.124*	0.388 (6)
H20B	0.192226	0.549728	0.354836	0.124*	0.388 (6)
C21	−0.051 (3)	0.4833 (14)	0.3361 (4)	0.099 (4)	0.388 (6)
H21A	−0.176717	0.472374	0.343864	0.119*	0.388 (6)
H21B	−0.052004	0.543380	0.321460	0.119*	0.388 (6)
C22	0.0237 (19)	0.3790 (8)	0.3220 (2)	0.076 (3)	0.388 (6)
H22A	0.126688	0.395255	0.308252	0.092*	0.388 (6)
H22B	−0.073782	0.341045	0.310661	0.092*	0.388 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1A	0.0481 (4)	0.0328 (3)	0.0460 (4)	−0.0038 (3)	−0.0006 (3)	0.0085 (3)
O1A	0.0720 (15)	0.0337 (10)	0.0485 (12)	−0.0026 (10)	−0.0117 (10)	0.0076 (9)
O2A	0.0746 (16)	0.0481 (12)	0.0454 (12)	−0.0180 (11)	0.0004 (11)	−0.0007 (10)
O3A	0.0704 (15)	0.0380 (11)	0.0561 (14)	−0.0073 (10)	0.0154 (11)	−0.0008 (9)
O4A	0.0480 (14)	0.0832 (19)	0.0869 (19)	−0.0059 (12)	−0.0004 (13)	0.0444 (15)
P1B	0.0406 (3)	0.0363 (3)	0.0366 (3)	−0.0006 (3)	0.0005 (3)	0.0031 (3)
O1B	0.0562 (12)	0.0322 (9)	0.0464 (11)	−0.0047 (9)	0.0093 (9)	−0.0043 (8)
O2B	0.0611 (14)	0.0418 (11)	0.0527 (12)	−0.0064 (10)	0.0132 (11)	−0.0088 (9)
O3B	0.0424 (11)	0.0631 (13)	0.0557 (12)	0.0005 (10)	−0.0036 (9)	0.0195 (11)
O4B	0.0473 (11)	0.0662 (14)	0.0475 (11)	0.0044 (11)	0.0017 (10)	0.0194 (10)
N1A	0.0613 (16)	0.0367 (12)	0.0432 (13)	0.0005 (12)	−0.0049 (12)	−0.0071 (10)
C1A	0.066 (2)	0.0307 (13)	0.0573 (18)	−0.0013 (14)	0.0017 (16)	−0.0025 (12)
N2A	0.0620 (16)	0.0399 (12)	0.0381 (12)	0.0007 (11)	−0.0038 (12)	0.0025 (10)
C2A	0.0613 (19)	0.0352 (14)	0.0453 (15)	−0.0039 (14)	−0.0004 (14)	0.0048 (12)
N3A	0.0545 (14)	0.0291 (10)	0.0418 (12)	−0.0008 (11)	−0.0041 (11)	0.0003 (9)
C3A	0.0430 (15)	0.0329 (13)	0.0405 (13)	0.0013 (11)	−0.0004 (12)	−0.0005 (10)
N4A	0.092 (2)	0.0513 (16)	0.0467 (15)	−0.0218 (16)	−0.0096 (15)	0.0009 (13)
C4A	0.0428 (15)	0.0357 (13)	0.0439 (15)	0.0020 (12)	−0.0038 (12)	−0.0013 (11)
N5A	0.0674 (17)	0.0466 (13)	0.0362 (12)	−0.0092 (13)	−0.0048 (12)	0.0033 (10)
C5A	0.0622 (18)	0.0363 (14)	0.0399 (14)	−0.0003 (14)	−0.0042 (14)	0.0051 (11)
N6A	0.181 (5)	0.123 (4)	0.055 (2)	0.069 (4)	−0.015 (3)	0.005 (2)
C6A	0.0411 (14)	0.0341 (13)	0.0387 (13)	0.0018 (12)	−0.0001 (11)	0.0030 (10)
C7A	0.0504 (16)	0.0340 (13)	0.0394 (14)	−0.0013 (13)	−0.0040 (12)	0.0000 (11)
C8A	0.080 (2)	0.0428 (17)	0.0464 (18)	−0.0162 (16)	−0.0062 (16)	0.0025 (13)
C9A	0.0552 (17)	0.0379 (14)	0.0410 (14)	−0.0053 (13)	−0.0010 (13)	−0.0001 (11)
C10A	0.070 (2)	0.0509 (17)	0.0374 (15)	−0.0004 (16)	0.0015 (15)	0.0019 (13)
C11A	0.075 (3)	0.079 (3)	0.0462 (19)	0.010 (2)	−0.0043 (18)	0.0017 (18)
C12A	0.098 (3)	0.082 (3)	0.050 (2)	0.028 (2)	−0.012 (2)	−0.0024 (19)
C13A	0.077 (2)	0.067 (2)	0.0519 (18)	0.003 (2)	0.0066 (17)	−0.0026 (17)
C14A	0.101 (3)	0.076 (3)	0.082 (3)	−0.004 (3)	0.004 (3)	−0.024 (2)
C15A	0.127 (5)	0.094 (4)	0.149 (6)	0.020 (4)	0.013 (4)	−0.041 (4)
C16A	0.099 (4)	0.130 (5)	0.133 (5)	0.029 (4)	0.016 (4)	−0.028 (4)
C17A	0.066 (3)	0.093 (3)	0.109 (3)	0.006 (2)	0.000 (2)	−0.016 (3)
N1B	0.0722 (18)	0.0368 (12)	0.0646 (16)	−0.0004 (13)	0.0084 (15)	0.0106 (12)
C1B	0.068 (2)	0.0318 (15)	0.084 (2)	−0.0075 (15)	0.0019 (19)	0.0005 (15)
N2B	0.086 (2)	0.0404 (13)	0.0429 (14)	0.0048 (14)	0.0076 (14)	0.0057 (11)
C2B	0.0595 (19)	0.0401 (15)	0.0617 (19)	−0.0045 (15)	−0.0040 (16)	−0.0043 (14)
N3B	0.0611 (15)	0.0312 (11)	0.0388 (12)	−0.0019 (11)	0.0045 (11)	0.0029 (9)
C3B	0.0428 (15)	0.0358 (14)	0.0523 (16)	0.0006 (11)	0.0054 (13)	−0.0004 (11)
N4B	0.109 (3)	0.0680 (18)	0.0426 (14)	0.012 (2)	−0.0125 (17)	−0.0003 (13)
C4B	0.0529 (16)	0.0344 (14)	0.0527 (16)	0.0023 (13)	0.0096 (14)	0.0063 (12)
N5B	0.085 (2)	0.0533 (15)	0.0370 (13)	0.0080 (15)	0.0016 (14)	0.0033 (11)
C5B	0.084 (2)	0.0430 (16)	0.0378 (15)	0.0037 (16)	0.0025 (16)	−0.0006 (12)
N6B	0.142 (4)	0.074 (3)	0.148 (4)	0.014 (3)	0.061 (4)	−0.002 (3)
C6B	0.0389 (13)	0.0396 (14)	0.0414 (13)	0.0014 (12)	0.0045 (12)	−0.0004 (11)
C7B	0.0427 (15)	0.0424 (15)	0.0400 (14)	−0.0009 (12)	−0.0009 (12)	0.0000 (11)
C8B	0.089 (3)	0.0479 (17)	0.0524 (18)	−0.0012 (19)	−0.0078 (19)	−0.0030 (14)
C9B	0.071 (2)	0.0471 (16)	0.0368 (14)	−0.0010 (16)	−0.0007 (15)	0.0037 (12)
C10B	0.119 (4)	0.072 (2)	0.0523 (19)	0.037 (3)	0.025 (2)	0.0273 (17)
C11B	0.146 (5)	0.050 (2)	0.075 (3)	0.016 (2)	0.048 (3)	0.0171 (19)
C12B	0.119 (4)	0.059 (2)	0.082 (3)	0.010 (3)	0.037 (3)	0.014 (2)
C13B	0.097 (5)	0.041 (3)	0.051 (4)	0.006 (3)	0.007 (4)	0.003 (3)
C14B	0.105 (5)	0.050 (3)	0.097 (5)	0.012 (4)	0.017 (4)	0.015 (3)
C15B	0.128 (10)	0.069 (6)	0.114 (9)	0.029 (6)	0.004 (7)	0.026 (6)
C16B	0.105 (6)	0.096 (6)	0.115 (7)	0.034 (5)	0.006 (5)	0.019 (5)
C17B	0.092 (5)	0.065 (4)	0.088 (5)	0.007 (4)	0.010 (4)	0.000 (4)
C18	0.075 (7)	0.065 (6)	0.058 (6)	0.011 (6)	0.001 (5)	0.015 (5)
C19	0.084 (7)	0.100 (8)	0.080 (7)	0.032 (6)	−0.005 (6)	−0.011 (6)
C20	0.120 (10)	0.078 (8)	0.113 (10)	−0.005 (8)	−0.002 (8)	0.000 (8)
C21	0.122 (11)	0.063 (8)	0.113 (10)	0.013 (7)	−0.012 (8)	0.011 (7)
C22	0.103 (7)	0.068 (6)	0.058 (5)	0.010 (5)	−0.018 (5)	0.016 (5)

Geometric parameters (Å, º)

P1A—O1A	1.498 (2)	N1B—C4B	1.345 (4)
P1A—O2A	1.522 (2)	C1B—H1BA	0.9300
P1A—O3A	1.535 (2)	C1B—C2B	1.355 (5)
P1A—O4A	1.543 (2)	N2B—C4B	1.336 (4)
O3A—H3AA	0.825 (14)	N2B—C5B	1.309 (4)
O4A—H4A	0.8200	C2B—H2B	0.9300
P1B—O1B	1.523 (2)	C2B—C3B	1.427 (4)
P1B—O2B	1.520 (2)	N3B—H3B	0.8600
P1B—O3B	1.504 (2)	N3B—C5B	1.361 (4)
P1B—O4B	1.559 (2)	N3B—C6B	1.364 (3)
O2B—H2BA	0.829 (14)	C3B—C4B	1.425 (4)
O4B—H4B	0.8200	C3B—C6B	1.393 (4)
N1A—H1A	0.8600	N4B—N5B	1.358 (4)
N1A—C1A	1.381 (4)	N4B—C8B	1.308 (5)
N1A—C4A	1.348 (3)	N5B—C9B	1.320 (4)
C1A—H1AA	0.9300	N5B—C10B	1.475 (4)
C1A—C2A	1.354 (4)	C5B—H5B	0.9300
N2A—C4A	1.347 (3)	N6B—C12B	1.124 (6)
N2A—C5A	1.320 (4)	C6B—C7B	1.444 (4)
C2A—H2A	0.9300	C7B—C8B	1.410 (4)
C2A—C3A	1.434 (4)	C7B—C9B	1.380 (4)
N3A—H3A	0.8600	C8B—H8B	0.9300
N3A—C5A	1.345 (4)	C9B—H9B	0.9300
N3A—C6A	1.358 (3)	C10B—H10A	0.9800
C3A—C4A	1.407 (4)	C10B—H10B	0.9800
C3A—C6A	1.399 (4)	C10B—C11B	1.519 (8)
N4A—N5A	1.360 (4)	C10B—C13B	1.564 (8)
N4A—C8A	1.333 (4)	C10B—C18	1.533 (12)
N5A—C9A	1.336 (4)	C11B—H11A	0.9700
N5A—C10A	1.468 (4)	C11B—H11B	0.9700
C5A—H5A	0.9300	C11B—C12B	1.457 (6)
N6A—C12A	1.118 (5)	C13B—H13B	0.9800
C6A—C7A	1.443 (4)	C13B—C14B	1.540 (9)
C7A—C8A	1.417 (4)	C13B—C17B	1.549 (11)
C7A—C9A	1.384 (4)	C14B—H14A	0.9700
C8A—H8A	0.9300	C14B—H14B	0.9700
C9A—H9A	0.9300	C14B—C15B	1.539 (14)
C10A—H10C	0.9800	C15B—H15A	0.9700
C10A—C11A	1.527 (5)	C15B—H15B	0.9700
C10A—C13A	1.517 (5)	C15B—C16B	1.531 (15)
C11A—H11C	0.9700	C16B—H16A	0.9700
C11A—H11D	0.9700	C16B—H16B	0.9700
C11A—C12A	1.455 (5)	C16B—C17B	1.519 (11)
C13A—H13A	0.9800	C17B—H17A	0.9700
C13A—C14A	1.511 (6)	C17B—H17B	0.9700
C13A—C17A	1.528 (6)	C18—H18	0.9800
C14A—H14C	0.9700	C18—C19	1.538 (15)
C14A—H14D	0.9700	C18—C22	1.538 (13)
C14A—C15A	1.531 (7)	C19—H19A	0.9700
C15A—H15C	0.9700	C19—H19B	0.9700
C15A—H15D	0.9700	C19—C20	1.561 (18)
C15A—C16A	1.477 (9)	C20—H20A	0.9700
C16A—H16C	0.9700	C20—H20B	0.9700
C16A—H16D	0.9700	C20—C21	1.528 (18)
C16A—C17A	1.521 (7)	C21—H21A	0.9700
C17A—H17C	0.9700	C21—H21B	0.9700
C17A—H17D	0.9700	C21—C22	1.503 (17)
N1B—H1B	0.8600	C22—H22A	0.9700
N1B—C1B	1.362 (4)	C22—H22B	0.9700
O1A—P1A—O2A	113.05 (13)	C5B—N3B—H3B	118.2
O1A—P1A—O3A	110.42 (13)	C5B—N3B—C6B	123.6 (2)
O1A—P1A—O4A	106.40 (14)	C6B—N3B—H3B	118.2
O2A—P1A—O3A	110.45 (13)	C4B—C3B—C2B	105.7 (3)
O2A—P1A—O4A	107.69 (16)	C6B—C3B—C2B	137.6 (3)
O3A—P1A—O4A	108.61 (17)	C6B—C3B—C4B	116.7 (3)
P1A—O3A—H3AA	116 (3)	C8B—N4B—N5B	104.9 (3)
P1A—O4A—H4A	109.5	N1B—C4B—C3B	108.3 (3)
O1B—P1B—O4B	109.16 (13)	N2B—C4B—N1B	125.0 (3)
O2B—P1B—O1B	110.98 (12)	N2B—C4B—C3B	126.7 (3)
O2B—P1B—O4B	108.57 (13)	N4B—N5B—C10B	120.8 (3)
O3B—P1B—O1B	112.26 (13)	C9B—N5B—N4B	111.5 (3)
O3B—P1B—O2B	111.55 (14)	C9B—N5B—C10B	127.4 (3)
O3B—P1B—O4B	104.02 (12)	N2B—C5B—N3B	124.3 (3)
P1B—O2B—H2BA	122 (3)	N2B—C5B—H5B	117.8
P1B—O4B—H4B	109.5	N3B—C5B—H5B	117.8
C1A—N1A—H1A	125.8	N3B—C6B—C3B	115.1 (2)
C4A—N1A—H1A	125.8	N3B—C6B—C7B	117.9 (2)
C4A—N1A—C1A	108.3 (2)	C3B—C6B—C7B	127.0 (3)
N1A—C1A—H1AA	124.9	C8B—C7B—C6B	130.0 (3)
C2A—C1A—N1A	110.3 (3)	C9B—C7B—C6B	127.3 (3)
C2A—C1A—H1AA	124.9	C9B—C7B—C8B	102.7 (3)
C5A—N2A—C4A	112.7 (2)	N4B—C8B—C7B	112.4 (3)
C1A—C2A—H2A	126.8	N4B—C8B—H8B	123.8
C1A—C2A—C3A	106.3 (3)	C7B—C8B—H8B	123.8
C3A—C2A—H2A	126.8	N5B—C9B—C7B	108.6 (3)
C5A—N3A—H3A	119.0	N5B—C9B—H9B	125.7
C5A—N3A—C6A	122.1 (2)	C7B—C9B—H9B	125.7
C6A—N3A—H3A	119.0	N5B—C10B—H10A	102.4
C4A—C3A—C2A	106.4 (2)	N5B—C10B—H10B	110.5
C6A—C3A—C2A	136.9 (3)	N5B—C10B—C11B	109.3 (3)
C6A—C3A—C4A	116.6 (2)	N5B—C10B—C13B	113.0 (4)
C8A—N4A—N5A	104.6 (3)	N5B—C10B—C18	107.0 (6)
N1A—C4A—C3A	108.6 (2)	C11B—C10B—H10A	102.4
N2A—C4A—N1A	124.9 (3)	C11B—C10B—H10B	110.5
N2A—C4A—C3A	126.5 (2)	C11B—C10B—C13B	102.8 (5)
N4A—N5A—C10A	119.7 (2)	C11B—C10B—C18	129.9 (7)
C9A—N5A—N4A	112.6 (2)	C13B—C10B—H10B	110.5
C9A—N5A—C10A	127.7 (3)	C18—C10B—H10A	102.4
N2A—C5A—N3A	125.8 (3)	C10B—C11B—H11A	109.1
N2A—C5A—H5A	117.1	C10B—C11B—H11B	109.1
N3A—C5A—H5A	117.1	H11A—C11B—H11B	107.8
N3A—C6A—C3A	116.3 (2)	C12B—C11B—C10B	112.6 (4)
N3A—C6A—C7A	118.6 (2)	C12B—C11B—H11A	109.1
C3A—C6A—C7A	125.1 (2)	C12B—C11B—H11B	109.1
C8A—C7A—C6A	127.8 (3)	N6B—C12B—C11B	179.2 (7)
C9A—C7A—C6A	128.0 (3)	C10B—C13B—H13B	109.4
C9A—C7A—C8A	104.1 (2)	C14B—C13B—C10B	116.9 (6)
N4A—C8A—C7A	111.4 (3)	C14B—C13B—H13B	109.4
N4A—C8A—H8A	124.3	C14B—C13B—C17B	105.5 (6)
C7A—C8A—H8A	124.3	C17B—C13B—C10B	106.0 (7)
N5A—C9A—C7A	107.3 (3)	C17B—C13B—H13B	109.4
N5A—C9A—H9A	126.3	C13B—C14B—H14A	111.0
C7A—C9A—H9A	126.3	C13B—C14B—H14B	111.0
N5A—C10A—H10C	107.1	H14A—C14B—H14B	109.0
N5A—C10A—C11A	106.1 (3)	C15B—C14B—C13B	103.6 (7)
N5A—C10A—C13A	114.5 (3)	C15B—C14B—H14A	111.0
C11A—C10A—H10C	107.1	C15B—C14B—H14B	111.0
C13A—C10A—H10C	107.1	C14B—C15B—H15A	111.1
C13A—C10A—C11A	114.6 (3)	C14B—C15B—H15B	111.1
C10A—C11A—H11C	109.0	H15A—C15B—H15B	109.1
C10A—C11A—H11D	109.0	C16B—C15B—C14B	103.2 (8)
H11C—C11A—H11D	107.8	C16B—C15B—H15A	111.1
C12A—C11A—C10A	113.1 (3)	C16B—C15B—H15B	111.1
C12A—C11A—H11C	109.0	C15B—C16B—H16A	110.7
C12A—C11A—H11D	109.0	C15B—C16B—H16B	110.7
N6A—C12A—C11A	178.6 (5)	H16A—C16B—H16B	108.8
C10A—C13A—H13A	106.5	C17B—C16B—C15B	105.0 (8)
C10A—C13A—C17A	114.0 (3)	C17B—C16B—H16A	110.7
C14A—C13A—C10A	118.4 (4)	C17B—C16B—H16B	110.7
C14A—C13A—H13A	106.5	C13B—C17B—H17A	110.3
C14A—C13A—C17A	104.1 (4)	C13B—C17B—H17B	110.3
C17A—C13A—H13A	106.5	C16B—C17B—C13B	107.0 (7)
C13A—C14A—H14C	110.7	C16B—C17B—H17A	110.3
C13A—C14A—H14D	110.7	C16B—C17B—H17B	110.3
C13A—C14A—C15A	105.0 (4)	H17A—C17B—H17B	108.6
H14C—C14A—H14D	108.8	C10B—C18—H18	110.4
C15A—C14A—H14C	110.7	C10B—C18—C19	105.8 (10)
C15A—C14A—H14D	110.7	C10B—C18—C22	114.1 (9)
C14A—C15A—H15C	110.2	C19—C18—H18	110.4
C14A—C15A—H15D	110.2	C22—C18—H18	110.4
H15C—C15A—H15D	108.5	C22—C18—C19	105.5 (9)
C16A—C15A—C14A	107.7 (4)	C18—C19—H19A	110.5
C16A—C15A—H15C	110.2	C18—C19—H19B	110.5
C16A—C15A—H15D	110.2	C18—C19—C20	106.0 (10)
C15A—C16A—H16C	110.3	H19A—C19—H19B	108.7
C15A—C16A—H16D	110.3	C20—C19—H19A	110.5
C15A—C16A—C17A	106.9 (5)	C20—C19—H19B	110.5
H16C—C16A—H16D	108.6	C19—C20—H20A	110.7
C17A—C16A—H16C	110.3	C19—C20—H20B	110.7
C17A—C16A—H16D	110.3	H20A—C20—H20B	108.8
C13A—C17A—H17C	111.0	C21—C20—C19	105.0 (12)
C13A—C17A—H17D	111.0	C21—C20—H20A	110.7
C16A—C17A—C13A	103.7 (4)	C21—C20—H20B	110.7
C16A—C17A—H17C	111.0	C20—C21—H21A	111.0
C16A—C17A—H17D	111.0	C20—C21—H21B	111.0
H17C—C17A—H17D	109.0	H21A—C21—H21B	109.0
C1B—N1B—H1B	125.6	C22—C21—C20	104.0 (12)
C4B—N1B—H1B	125.6	C22—C21—H21A	111.0
C4B—N1B—C1B	108.8 (3)	C22—C21—H21B	111.0
N1B—C1B—H1BA	124.7	C18—C22—H22A	110.8
C2B—C1B—N1B	110.6 (3)	C18—C22—H22B	110.8
C2B—C1B—H1BA	124.7	C21—C22—C18	105.0 (10)
C5B—N2B—C4B	113.5 (3)	C21—C22—H22A	110.8
C1B—C2B—H2B	126.7	C21—C22—H22B	110.8
C1B—C2B—C3B	106.6 (3)	H22A—C22—H22B	108.8
C3B—C2B—H2B	126.7
N1A—C1A—C2A—C3A	0.4 (4)	C2B—C3B—C6B—N3B	176.7 (3)
C1A—N1A—C4A—N2A	−177.1 (3)	C2B—C3B—C6B—C7B	−4.3 (6)
C1A—N1A—C4A—C3A	1.4 (4)	N3B—C6B—C7B—C8B	174.6 (3)
C1A—C2A—C3A—C4A	0.4 (4)	N3B—C6B—C7B—C9B	−5.8 (5)
C1A—C2A—C3A—C6A	176.4 (3)	C3B—C6B—C7B—C8B	−4.4 (5)
C2A—C3A—C4A—N1A	−1.1 (3)	C3B—C6B—C7B—C9B	175.2 (3)
C2A—C3A—C4A—N2A	177.4 (3)	N4B—N5B—C9B—C7B	−0.1 (4)
C2A—C3A—C6A—N3A	−175.1 (3)	N4B—N5B—C10B—C11B	−101.8 (4)
C2A—C3A—C6A—C7A	4.2 (6)	N4B—N5B—C10B—C13B	144.5 (5)
N3A—C6A—C7A—C8A	22.2 (5)	N4B—N5B—C10B—C18	113.4 (6)
N3A—C6A—C7A—C9A	−160.8 (3)	C4B—N1B—C1B—C2B	−0.5 (4)
C3A—C6A—C7A—C8A	−157.2 (3)	C4B—N2B—C5B—N3B	−1.8 (5)
C3A—C6A—C7A—C9A	19.9 (5)	C4B—C3B—C6B—N3B	−0.6 (4)
N4A—N5A—C9A—C7A	1.0 (4)	C4B—C3B—C6B—C7B	178.5 (3)
N4A—N5A—C10A—C11A	57.3 (4)	N5B—N4B—C8B—C7B	−0.7 (5)
N4A—N5A—C10A—C13A	−70.1 (4)	N5B—C10B—C11B—C12B	62.2 (5)
C4A—N1A—C1A—C2A	−1.1 (4)	N5B—C10B—C13B—C14B	171.1 (6)
C4A—N2A—C5A—N3A	−0.3 (5)	N5B—C10B—C13B—C17B	−71.8 (6)
C4A—C3A—C6A—N3A	0.6 (4)	N5B—C10B—C18—C19	98.4 (9)
C4A—C3A—C6A—C7A	180.0 (3)	N5B—C10B—C18—C22	−146.1 (9)
N5A—N4A—C8A—C7A	2.0 (4)	C5B—N2B—C4B—N1B	−178.1 (3)
N5A—C10A—C11A—C12A	−178.0 (3)	C5B—N2B—C4B—C3B	2.1 (5)
N5A—C10A—C13A—C14A	70.9 (4)	C5B—N3B—C6B—C3B	0.9 (4)
N5A—C10A—C13A—C17A	−52.0 (5)	C5B—N3B—C6B—C7B	−178.2 (3)
C5A—N2A—C4A—N1A	177.6 (3)	C6B—N3B—C5B—N2B	0.3 (5)
C5A—N2A—C4A—C3A	−0.6 (4)	C6B—C3B—C4B—N1B	179.2 (3)
C5A—N3A—C6A—C3A	−1.4 (4)	C6B—C3B—C4B—N2B	−1.0 (5)
C5A—N3A—C6A—C7A	179.2 (3)	C6B—C7B—C8B—N4B	−179.7 (3)
C6A—N3A—C5A—N2A	1.3 (5)	C6B—C7B—C9B—N5B	−180.0 (3)
C6A—C3A—C4A—N1A	−178.1 (3)	C8B—N4B—N5B—C9B	0.5 (5)
C6A—C3A—C4A—N2A	0.4 (5)	C8B—N4B—N5B—C10B	175.1 (4)
C6A—C7A—C8A—N4A	176.2 (3)	C8B—C7B—C9B—N5B	−0.3 (4)
C6A—C7A—C9A—N5A	−177.4 (3)	C9B—N5B—C10B—C11B	71.9 (5)
C8A—N4A—N5A—C9A	−1.9 (4)	C9B—N5B—C10B—C13B	−41.9 (7)
C8A—N4A—N5A—C10A	178.6 (3)	C9B—N5B—C10B—C18	−72.9 (8)
C8A—C7A—C9A—N5A	0.2 (4)	C9B—C7B—C8B—N4B	0.6 (4)
C9A—N5A—C10A—C11A	−122.2 (4)	C10B—N5B—C9B—C7B	−174.3 (4)
C9A—N5A—C10A—C13A	110.4 (4)	C10B—C13B—C14B—C15B	144.7 (9)
C9A—C7A—C8A—N4A	−1.4 (4)	C10B—C13B—C17B—C16B	−129.5 (6)
C10A—N5A—C9A—C7A	−179.5 (3)	C10B—C18—C19—C20	129.7 (12)
C10A—C13A—C14A—C15A	−158.0 (4)	C10B—C18—C22—C21	−145.0 (13)
C10A—C13A—C17A—C16A	166.1 (4)	C11B—C10B—C13B—C14B	53.5 (8)
C11A—C10A—C13A—C14A	−52.0 (5)	C11B—C10B—C13B—C17B	170.6 (5)
C11A—C10A—C13A—C17A	−174.9 (4)	C11B—C10B—C18—C19	−36.5 (11)
C13A—C10A—C11A—C12A	−50.7 (5)	C11B—C10B—C18—C22	79.0 (12)
C13A—C14A—C15A—C16A	13.4 (7)	C13B—C10B—C11B—C12B	−177.6 (4)
C14A—C13A—C17A—C16A	35.7 (5)	C13B—C14B—C15B—C16B	−39.3 (11)
C14A—C15A—C16A—C17A	9.1 (7)	C14B—C13B—C17B—C16B	−5.0 (9)
C15A—C16A—C17A—C13A	−27.7 (6)	C14B—C15B—C16B—C17B	36.4 (11)
C17A—C13A—C14A—C15A	−30.3 (5)	C15B—C16B—C17B—C13B	−19.5 (11)
N1B—C1B—C2B—C3B	1.2 (4)	C17B—C13B—C14B—C15B	27.2 (10)
C1B—N1B—C4B—N2B	179.8 (3)	C18—C10B—C11B—C12B	−163.6 (7)
C1B—N1B—C4B—C3B	−0.4 (4)	C18—C19—C20—C21	14.9 (19)
C1B—C2B—C3B—C4B	−1.4 (4)	C19—C18—C22—C21	−29.3 (15)
C1B—C2B—C3B—C6B	−178.9 (4)	C19—C20—C21—C22	−33 (2)
C2B—C3B—C4B—N1B	1.1 (4)	C20—C21—C22—C18	38.8 (19)
C2B—C3B—C4B—N2B	−179.1 (3)	C22—C18—C19—C20	8.5 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3AA···O1B	0.83 (1)	1.70 (2)	2.525 (3)	173 (4)
O4A—H4A···O3B^i	0.82	1.71	2.519 (3)	171
O2B—H2BA···O2A	0.83 (1)	1.67 (2)	2.473 (3)	162 (4)
O4B—H4B···O3B^ii	0.82	1.81	2.575 (3)	154
N1A—H1A···O2B^iii	0.86	1.99	2.819 (3)	161
N3A—H3A···O1A	0.86	1.73	2.578 (3)	170
N1B—H1B···N2A^iv	0.86	2.35	3.120 (4)	149
N3B—H3B···O1B	0.86	1.89	2.729 (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) x−1/2, −y+1/2, −z+1.