Solvomorphs of tyraminium 5,5-di­ethyl­barbiturate: a rare example of the barbiturate R33(12) hydrogen-bond motif and a crystal structure with Z′ = 4

Rydz, A.; Gryl, M.; Stadnicka, K.M.

doi:10.1107/S205322961801433X

Solvomorphs of tyraminium 5,5-diethylbarbiturate: a rare example of the barbiturate R₃³(12) hydrogen-bond motif and a crystal structure with Z′ = 4

In the past two decades, the solvomorphism phenomenon in organic materials has attracted much attention, especially in the pharmaceutical and materials industries. Cocrystallization with solvent molecules can lead to modified physical and chemical properties of materials. We present here two new solvomorphs (pseudopolymorphs) of tyraminium 5,5-diethylbarbiturate [2-(4-hydroxyphenyl)ethanaminium 5,5-diethyl-2,4,6-trioxotetrahydro-2H-pyrimidin-1-ide, C₈H₁₂NO⁺·C₈H₁₁N₂O₃⁻] with unusual structural features. Pseudopolymorph (I) follows the symmetry of the P2₁/n space group and has four tyraminium cations, four barbitalate anions and four molecules of chloroform in the asymmetric unit. Pseudopolymorph (II) crystallizes in the space group R $\overline{3}$ c with one tyraminium cation, one barbitalate anion and a small amount of disordered solvent (ethanol and water) located in the cavities. Hirshfeld surface analysis and the Non-Covalent Interaction (NCI) index were used to examine and compare the crystal packing features and intermolecular interactions in (I) and (II). Both materials crystallize with large unit cells and contain nontypical barbitalate ions formed through deprotonation of the barbital N3 position. Pseudopolymorph (I) is an example of a crystal structure with a rarely observed value of Z′ = 4. Analysis of the hydrogen-bond patterns in (II) showed an unusual arrangement of three barbitalate anions in R₃³(12) rings, which is the first example of such a hydrogen-bond motif in barbital structures. The mutual arrangement of the ions in the crystal structure of (II) leads to the formation of specific cavities along the c direction.

Keywords: solvomorphs; tyramine; barbital; barbiturate; API; hydrogen bonding; crystal structure; high Z′.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961801433X/ku3228sup1.cif Contains datablocks I, II, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961801433X/ku3228Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961801433X/ku3228IIsup3.hkl Contains datablock II
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961801433X/ku3228Isup4.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961801433X/ku3228IIsup5.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S205322961801433X/ku3228sup6.pdf Complete additional data for (I) and (II), including hydrogen-bond geometry
	Portable Document Format (PDF) file https://doi.org/10.1107/S205322961801433X/ku3228sup7.pdf Data before SQUEEZE, conoscopic image of (II), and interaction and packing information

CCDC references: 1860215; 1860216

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a) for (I); SIR92 (Altomare et al., 1994) for (II). For both structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

2-(4-Hydroxyphenyl)ethanaminium 5,5-diethyl-2,4,6-trioxotetrahydro-2H-pyrimidin-1-ide chloroform monosolvate (I) top

Crystal data top

C₈H₁₂NO⁺·C₈H₁₁N₂O₃⁻·CHCl₃	F(000) = 3680
M_r = 440.74	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 19.8159 (2) Å	Cell parameters from 56525 reflections
b = 17.7138 (1) Å	θ = 2.9–31.5°
c = 25.5074 (2) Å	µ = 0.45 mm⁻¹
β = 104.299 (1)°	T = 130 K
V = 8676.10 (13) Å³	Plate, colourless
Z = 16	0.43 × 0.40 × 0.30 mm

Data collection top

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	25278 independent reflections
Radiation source: micro-focus sealed X-ray tube	17781 reflections with I > 2σ(I)
Detector resolution: 10.3756' pixels mm^-1	R_int = 0.052
ω scans	θ_max = 30.0°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −27→27
T_min = 0.769, T_max = 1.000	k = −24→24
245170 measured reflections	l = −35→35

Refinement top

Refinement on F²	40 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0552P)² + 2.3099P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
25278 reflections	Δρ_max = 0.53 e Å⁻³
1211 parameters	Δρ_min = −0.46 e Å⁻³

Special details top

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

Refinement. Large unit cell is a cause of missing reflections below Theta(Min). Distance from detector to crystal is set to 73 mm and this cannot be a reason for missing reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1A	0.36861 (7)	0.12333 (8)	−0.11878 (6)	0.0244 (3)
O1A	0.37299 (5)	0.05132 (6)	−0.13698 (4)	0.0310 (2)
H1A	0.4107 (10)	0.0344 (11)	−0.1272 (7)	0.037*
C2A	0.42134 (7)	0.15582 (8)	−0.07881 (6)	0.0284 (3)
H2A	0.462194	0.127879	−0.062912	0.034*
C3A	0.41379 (8)	0.22945 (9)	−0.06234 (6)	0.0313 (3)
H3A	0.449918	0.251429	−0.035047	0.038*
C4A	0.35442 (7)	0.27184 (8)	−0.08495 (6)	0.0261 (3)
C5A	0.30217 (7)	0.23780 (8)	−0.12436 (6)	0.0285 (3)
H5A	0.261043	0.265472	−0.139967	0.034*
C6A	0.30861 (7)	0.16445 (8)	−0.14144 (6)	0.0295 (3)
H6A	0.272261	0.142350	−0.168482	0.035*
C7A	0.34846 (8)	0.35298 (8)	−0.06836 (6)	0.0301 (3)
H7A1	0.365614	0.357609	−0.028610	0.036*
H7A2	0.298976	0.368649	−0.078460	0.036*
C8A	0.39076 (7)	0.40441 (8)	−0.09596 (6)	0.0263 (3)
H8A1	0.439983	0.387799	−0.086287	0.032*
H8A2	0.373147	0.399756	−0.135669	0.032*
N2A	0.38714 (6)	0.48488 (6)	−0.08021 (5)	0.0210 (2)
H11A	0.3435 (6)	0.5030 (9)	−0.0932 (7)	0.031*
H12A	0.4204 (7)	0.5103 (9)	−0.0918 (7)	0.031*
H13A	0.3969 (9)	0.4853 (10)	−0.0435 (4)	0.031*
C1B	0.67898 (7)	0.37382 (8)	0.20361 (5)	0.0227 (3)
O1B	0.66249 (5)	0.44645 (6)	0.18814 (4)	0.0251 (2)
H1B	0.6255 (9)	0.4584 (10)	0.1934 (7)	0.030*
C2B	0.63999 (8)	0.32984 (9)	0.23086 (6)	0.0302 (3)
H2B	0.599185	0.349828	0.238860	0.036*
C3B	0.66135 (8)	0.25661 (9)	0.24617 (6)	0.0336 (3)
H3B	0.634581	0.226988	0.264657	0.040*
C4B	0.72094 (8)	0.22547 (8)	0.23515 (6)	0.0300 (3)
C5B	0.75851 (7)	0.26987 (8)	0.20737 (6)	0.0304 (3)
H5B	0.798916	0.249630	0.198868	0.036*
C6B	0.73808 (7)	0.34334 (8)	0.19178 (6)	0.0275 (3)
H6B	0.764638	0.372741	0.172987	0.033*
C7B	0.74273 (9)	0.14538 (9)	0.25192 (7)	0.0357 (3)
H7B1	0.734661	0.135169	0.288043	0.043*
H7B2	0.793103	0.139258	0.254489	0.043*
C8B	0.70187 (7)	0.08948 (8)	0.21139 (6)	0.0245 (3)
H8B1	0.651463	0.100252	0.204944	0.029*
H8B2	0.715021	0.094858	0.176568	0.029*
N2B	0.71618 (6)	0.01076 (6)	0.23188 (5)	0.0215 (2)
H11B	0.6860 (7)	−0.0171 (9)	0.2067 (6)	0.032*
H12B	0.7074 (9)	0.0060 (10)	0.2653 (4)	0.032*
H13B	0.7608 (5)	−0.0032 (9)	0.2336 (7)	0.032*
C1C	0.31853 (7)	0.63016 (7)	0.29378 (5)	0.0217 (3)
O1C	0.33471 (5)	0.55846 (5)	0.31199 (4)	0.0248 (2)
H1C	0.3715 (9)	0.5464 (10)	0.3067 (7)	0.030*
C2C	0.35778 (7)	0.67050 (8)	0.26487 (6)	0.0266 (3)
H2C	0.397580	0.648023	0.256829	0.032*
C3C	0.33859 (7)	0.74364 (8)	0.24784 (6)	0.0289 (3)
H3C	0.365784	0.770710	0.228261	0.035*
C4C	0.28039 (7)	0.77824 (8)	0.25880 (6)	0.0262 (3)
C5C	0.24167 (7)	0.73693 (8)	0.28758 (6)	0.0268 (3)
H5C	0.201872	0.759443	0.295609	0.032*
C6C	0.25981 (7)	0.66365 (8)	0.30483 (6)	0.0248 (3)
H6C	0.232335	0.636425	0.324095	0.030*
C7C	0.26178 (8)	0.85881 (8)	0.24229 (6)	0.0302 (3)
H7C1	0.211513	0.867037	0.239130	0.036*
H7C2	0.270984	0.868513	0.206472	0.036*
C8C	0.30401 (7)	0.91336 (8)	0.28358 (6)	0.0246 (3)
H8C1	0.294514	0.903901	0.319334	0.030*
H8C2	0.354279	0.904823	0.286959	0.030*
N2C	0.28615 (6)	0.99288 (6)	0.26716 (5)	0.0213 (2)
H11C	0.3159 (7)	1.0201 (9)	0.2930 (6)	0.032*
H12C	0.2412 (5)	1.0021 (10)	0.2679 (7)	0.032*
H13C	0.2935 (9)	1.0006 (10)	0.2337 (4)	0.032*
C1D	0.62991 (7)	0.87937 (8)	0.61406 (6)	0.0255 (3)
O1D	0.62634 (5)	0.95053 (6)	0.63429 (4)	0.0320 (2)
H1D	0.5876 (10)	0.9685 (11)	0.6244 (8)	0.038*
C2D	0.57738 (7)	0.84983 (8)	0.57256 (6)	0.0282 (3)
H2D	0.537519	0.879321	0.556707	0.034*
C3D	0.58372 (8)	0.77675 (9)	0.55448 (6)	0.0309 (3)
H3D	0.547583	0.756598	0.526307	0.037*
C4D	0.64191 (7)	0.73226 (8)	0.57674 (6)	0.0275 (3)
C5D	0.69429 (8)	0.76385 (9)	0.61736 (6)	0.0320 (3)
H5D	0.734728	0.734947	0.632698	0.038*
C6D	0.68886 (8)	0.83653 (9)	0.63599 (6)	0.0323 (3)
H6D	0.725381	0.857027	0.663708	0.039*
C7D	0.64576 (8)	0.65100 (8)	0.55966 (6)	0.0306 (3)
H7D1	0.695083	0.635388	0.565921	0.037*
H7D2	0.623520	0.645782	0.520566	0.037*
C8D	0.60876 (8)	0.60069 (8)	0.59204 (6)	0.0287 (3)
H8D1	0.629757	0.608529	0.631094	0.034*
H8D2	0.559216	0.615863	0.584597	0.034*
N2D	0.61273 (6)	0.51898 (7)	0.57921 (5)	0.0216 (2)
H11D	0.6020 (9)	0.5139 (10)	0.5429 (4)	0.032*
H12D	0.5802 (7)	0.4951 (9)	0.5921 (7)	0.032*
H13D	0.6564 (6)	0.5008 (9)	0.5917 (7)	0.032*
N1E	0.54458 (6)	−0.01240 (7)	−0.17213 (5)	0.0228 (2)
H1E	0.5035 (6)	−0.0149 (9)	−0.1948 (6)	0.027*
C2E	0.59888 (7)	−0.01323 (8)	−0.19839 (6)	0.0254 (3)
O2E	0.58221 (5)	−0.01958 (8)	−0.24838 (4)	0.0408 (3)
N3E	0.66579 (6)	−0.00755 (7)	−0.17063 (5)	0.0236 (2)
C4E	0.68281 (7)	−0.00195 (7)	−0.11621 (5)	0.0216 (3)
O4E	0.74413 (5)	0.00157 (7)	−0.09019 (4)	0.0325 (2)
C5E	0.62721 (6)	0.00203 (7)	−0.08349 (5)	0.0209 (2)
C6E	0.55330 (6)	−0.00505 (7)	−0.11807 (5)	0.0201 (2)
O6E	0.50308 (5)	−0.00342 (6)	−0.09768 (4)	0.0260 (2)
C7E	0.64044 (7)	−0.06074 (8)	−0.04021 (6)	0.0282 (3)
H7E1	0.686220	−0.051711	−0.014711	0.034*
H7E2	0.604453	−0.057217	−0.019437	0.034*
C8E	0.63970 (10)	−0.14044 (9)	−0.06283 (8)	0.0397 (4)
H81E	0.6759 (9)	−0.1457 (12)	−0.0827 (8)	0.060*
H82E	0.5938 (7)	−0.1528 (12)	−0.0865 (7)	0.060*
H83E	0.6478 (11)	−0.1775 (10)	−0.0333 (6)	0.060*
C9E	0.63357 (8)	0.07983 (8)	−0.05473 (6)	0.0287 (3)
H9E1	0.599662	0.081842	−0.032030	0.034*
H9E2	0.680777	0.084271	−0.030385	0.034*
C10E	0.62097 (10)	0.14696 (9)	−0.09309 (8)	0.0408 (4)
H10E	0.5744 (6)	0.1466 (12)	−0.1173 (7)	0.061*
H11E	0.6532 (9)	0.1482 (12)	−0.1165 (7)	0.061*
H12E	0.6242 (11)	0.1936 (8)	−0.0724 (8)	0.061*
N1F	0.42888 (6)	0.50181 (7)	0.18497 (4)	0.0244 (2)
H1F	0.4345 (9)	0.5060 (9)	0.2203 (4)	0.029*
C2F	0.48900 (7)	0.49390 (8)	0.16679 (5)	0.0220 (3)
O2F	0.54524 (5)	0.49721 (7)	0.20212 (4)	0.0330 (2)
N3F	0.48712 (6)	0.48364 (7)	0.11463 (4)	0.0221 (2)
C4F	0.42511 (7)	0.48047 (8)	0.07772 (5)	0.0228 (3)
O4F	0.42386 (6)	0.47125 (7)	0.02967 (4)	0.0382 (3)
C5F	0.35504 (7)	0.48650 (8)	0.09310 (5)	0.0223 (3)
C6F	0.36314 (7)	0.49848 (8)	0.15328 (5)	0.0227 (3)
O6F	0.31285 (5)	0.50441 (7)	0.17279 (4)	0.0333 (2)
C7F	0.31193 (7)	0.55249 (9)	0.06233 (6)	0.0293 (3)
H7F1	0.304689	0.543735	0.022995	0.035*
H7F2	0.265586	0.552569	0.070448	0.035*
C8F	0.34512 (10)	0.62998 (10)	0.07608 (8)	0.0433 (4)
H81F	0.3901 (7)	0.6317 (13)	0.0665 (9)	0.065*
H83F	0.3505 (11)	0.6431 (13)	0.1142 (5)	0.065*
H82F	0.3155 (10)	0.6691 (10)	0.0547 (8)	0.065*
C9F	0.31394 (7)	0.41235 (9)	0.07711 (6)	0.0307 (3)
H9F1	0.268229	0.416970	0.085998	0.037*
H9F2	0.305119	0.405549	0.037469	0.037*
C10F	0.35083 (10)	0.34251 (10)	0.10497 (9)	0.0459 (4)
H10F	0.3608 (12)	0.3474 (13)	0.1445 (4)	0.069*
H11F	0.3940 (8)	0.3329 (13)	0.0941 (9)	0.069*
H12F	0.3231 (10)	0.2963 (8)	0.0957 (9)	0.069*
N1G	0.56928 (6)	0.49797 (7)	0.31382 (4)	0.0229 (2)
H1G	0.5641 (9)	0.4992 (9)	0.2784 (4)	0.027*
C2G	0.50907 (6)	0.50621 (7)	0.33189 (5)	0.0204 (2)
O2G	0.45327 (5)	0.51142 (6)	0.29605 (4)	0.0301 (2)
N3G	0.51008 (6)	0.50865 (7)	0.38419 (4)	0.0217 (2)
C4G	0.57128 (7)	0.49991 (8)	0.42173 (5)	0.0251 (3)
O4G	0.57145 (6)	0.50160 (9)	0.46992 (4)	0.0497 (4)
C5G	0.64069 (7)	0.48661 (8)	0.40685 (5)	0.0221 (3)
C6G	0.63423 (7)	0.48944 (8)	0.34636 (5)	0.0213 (2)
O6G	0.68484 (5)	0.48377 (6)	0.32717 (4)	0.0305 (2)
C7G	0.66950 (8)	0.40825 (9)	0.42806 (6)	0.0321 (3)
H7G1	0.716157	0.401814	0.421122	0.039*
H7G2	0.675233	0.406741	0.467719	0.039*
C8G	0.62353 (12)	0.34225 (10)	0.40254 (8)	0.0481 (5)
H83G	0.5778 (7)	0.3463 (13)	0.4103 (9)	0.072*
H82G	0.6158 (12)	0.3385 (13)	0.3633 (4)	0.072*
H81G	0.6446 (11)	0.2944 (8)	0.4167 (9)	0.072*
C9G	0.69306 (7)	0.54798 (8)	0.43409 (6)	0.0272 (3)
H9G1	0.699405	0.544818	0.473759	0.033*
H9G2	0.738658	0.537417	0.426275	0.033*
C10G	0.67099 (9)	0.62782 (10)	0.41575 (7)	0.0386 (4)
H10G	0.7044 (9)	0.6638 (10)	0.4370 (7)	0.058*
H11G	0.6705 (11)	0.6345 (12)	0.3775 (4)	0.058*
H12G	0.6245 (7)	0.6386 (12)	0.4213 (8)	0.058*
N1H	0.45599 (6)	0.99824 (7)	0.67287 (5)	0.0226 (2)
H1H	0.4976 (5)	0.9923 (9)	0.6943 (6)	0.027*
C2H	0.40152 (7)	0.99296 (8)	0.69890 (5)	0.0225 (3)
O2H	0.41817 (5)	0.98367 (7)	0.74855 (4)	0.0325 (2)
N3H	0.33437 (5)	0.99736 (6)	0.67115 (4)	0.0217 (2)
C4H	0.31752 (6)	1.00982 (7)	0.61710 (5)	0.0206 (2)
O4H	0.25619 (5)	1.01552 (6)	0.59123 (4)	0.0281 (2)
C5H	0.37361 (6)	1.01868 (8)	0.58497 (5)	0.0217 (3)
C6H	0.44720 (6)	1.00766 (7)	0.61896 (5)	0.0197 (2)
O6H	0.49736 (5)	1.00817 (6)	0.59835 (4)	0.0255 (2)
C7H	0.36888 (8)	1.09914 (9)	0.56058 (7)	0.0329 (3)
H7H1	0.402574	1.103161	0.537804	0.040*
H7H2	0.321675	1.106323	0.536738	0.040*
C8H	0.38322 (10)	1.16237 (10)	0.60215 (9)	0.0453 (4)
H83H	0.3507 (10)	1.1608 (13)	0.6256 (8)	0.068*
H81H	0.4301 (7)	1.1601 (13)	0.6267 (8)	0.068*
H82H	0.3812 (11)	1.2130 (7)	0.5863 (8)	0.068*
C9H	0.35930 (7)	0.96051 (9)	0.53852 (6)	0.0301 (3)
H9H1	0.312488	0.970257	0.514744	0.036*
H9H2	0.393682	0.968062	0.516671	0.036*
C10H	0.36276 (9)	0.87869 (10)	0.55718 (8)	0.0392 (4)
H10H	0.4102 (6)	0.8639 (12)	0.5769 (8)	0.059*
H11H	0.3303 (9)	0.8692 (12)	0.5801 (7)	0.059*
H12H	0.3498 (10)	0.8444 (10)	0.5261 (6)	0.059*
C11	0.44411 (9)	1.25688 (10)	0.78116 (8)	0.0418 (4)
H11	0.4020 (10)	1.2598 (11)	0.7906 (8)	0.050*
Cl11	0.4528 (2)	1.1606 (2)	0.77201 (16)	0.0450 (8)	0.64 (3)
Cl12	0.43915 (14)	1.3065 (2)	0.72001 (14)	0.0528 (10)	0.64 (3)
Cl13	0.51153 (2)	1.29464 (3)	0.83282 (2)	0.04587 (11)
Cl14	0.4675 (13)	1.1630 (5)	0.7679 (5)	0.077 (2)	0.36 (3)
Cl15	0.4362 (4)	1.3129 (6)	0.7238 (4)	0.093 (3)	0.36 (3)
C22	0.60541 (9)	1.25626 (10)	0.59427 (7)	0.0373 (4)
H22	0.6300 (10)	1.2573 (11)	0.6302 (8)	0.045*
Cl21	0.53840 (19)	1.3222 (2)	0.58980 (13)	0.0588 (5)	0.66 (2)
Cl22	0.56954 (18)	1.16469 (18)	0.58074 (18)	0.0444 (6)	0.66 (2)
Cl23	0.66780 (18)	1.2756 (2)	0.55699 (12)	0.0586 (6)	0.66 (2)
Cl24	0.5414 (4)	1.3264 (4)	0.5735 (9)	0.084 (3)	0.34 (2)
Cl25	0.5753 (4)	1.1663 (4)	0.5758 (4)	0.0619 (18)	0.34 (2)
Cl26	0.6554 (8)	1.2861 (6)	0.5518 (4)	0.0811 (18)	0.34 (2)
C33	0.44699 (9)	0.23011 (10)	0.27147 (7)	0.0400 (4)
H33	0.4042 (10)	0.2090 (11)	0.2764 (8)	0.048*
Cl31	0.4443 (3)	0.3301 (3)	0.2752 (3)	0.0440 (10)	0.49 (3)
Cl32	0.51752 (2)	0.19366 (3)	0.32079 (2)	0.04835 (11)
Cl33	0.4454 (5)	0.2018 (4)	0.2075 (2)	0.0482 (8)	0.49 (3)
Cl34	0.4417 (3)	0.3275 (3)	0.2792 (3)	0.0519 (10)	0.51 (3)
Cl36	0.4627 (8)	0.2091 (3)	0.2057 (2)	0.0525 (12)	0.51 (3)
C44	0.39485 (9)	−0.24985 (10)	−0.09139 (7)	0.0398 (4)
H44	0.3687 (10)	−0.2556 (11)	−0.1289 (8)	0.048*
Cl41	0.43767 (11)	−0.15986 (15)	−0.08628 (13)	0.0519 (6)	0.651 (17)
Cl42	0.3386 (2)	−0.2515 (3)	−0.05091 (13)	0.0824 (8)	0.651 (17)
Cl43	0.45674 (14)	−0.32033 (17)	−0.0816 (3)	0.0590 (7)	0.651 (17)
Cl44	0.4298 (5)	−0.1651 (4)	−0.0766 (4)	0.0866 (18)	0.349 (17)
Cl45	0.3289 (4)	−0.2675 (7)	−0.0527 (2)	0.0771 (17)	0.349 (17)
Cl46	0.4545 (3)	−0.3260 (4)	−0.0626 (4)	0.0584 (12)	0.349 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0226 (6)	0.0234 (7)	0.0278 (7)	−0.0004 (5)	0.0073 (5)	−0.0033 (5)
O1A	0.0237 (5)	0.0254 (5)	0.0403 (6)	0.0031 (4)	0.0011 (4)	−0.0089 (4)
C2A	0.0228 (6)	0.0308 (8)	0.0298 (7)	0.0012 (5)	0.0029 (5)	−0.0045 (6)
C3A	0.0282 (7)	0.0313 (8)	0.0328 (8)	−0.0034 (6)	0.0047 (6)	−0.0086 (6)
C4A	0.0295 (7)	0.0241 (7)	0.0284 (7)	−0.0027 (5)	0.0139 (6)	−0.0027 (5)
C5A	0.0260 (7)	0.0250 (7)	0.0341 (8)	0.0035 (5)	0.0065 (6)	0.0010 (6)
C6A	0.0248 (7)	0.0280 (7)	0.0319 (7)	0.0003 (5)	−0.0001 (6)	−0.0047 (6)
C7A	0.0332 (7)	0.0245 (7)	0.0375 (8)	−0.0027 (6)	0.0182 (6)	−0.0054 (6)
C8A	0.0306 (7)	0.0244 (7)	0.0268 (7)	−0.0004 (5)	0.0126 (6)	−0.0043 (5)
N2A	0.0205 (5)	0.0244 (6)	0.0182 (5)	−0.0006 (4)	0.0052 (4)	−0.0013 (4)
C1B	0.0209 (6)	0.0243 (7)	0.0217 (6)	−0.0027 (5)	0.0029 (5)	−0.0002 (5)
O1B	0.0194 (4)	0.0264 (5)	0.0302 (5)	0.0031 (4)	0.0075 (4)	0.0032 (4)
C2B	0.0290 (7)	0.0327 (8)	0.0318 (8)	−0.0036 (6)	0.0130 (6)	−0.0005 (6)
C3B	0.0390 (8)	0.0312 (8)	0.0324 (8)	−0.0089 (6)	0.0121 (6)	0.0037 (6)
C4B	0.0337 (7)	0.0232 (7)	0.0290 (7)	−0.0056 (6)	−0.0001 (6)	0.0005 (6)
C5B	0.0246 (7)	0.0265 (7)	0.0389 (8)	−0.0007 (5)	0.0056 (6)	0.0013 (6)
C6B	0.0235 (6)	0.0250 (7)	0.0350 (8)	−0.0032 (5)	0.0091 (6)	0.0023 (6)
C7B	0.0408 (9)	0.0246 (7)	0.0349 (8)	−0.0055 (6)	−0.0037 (7)	0.0041 (6)
C8B	0.0245 (6)	0.0239 (7)	0.0246 (7)	−0.0002 (5)	0.0054 (5)	0.0028 (5)
N2B	0.0193 (5)	0.0230 (6)	0.0230 (6)	0.0009 (4)	0.0068 (4)	0.0004 (4)
C1C	0.0211 (6)	0.0211 (6)	0.0219 (6)	−0.0016 (5)	0.0030 (5)	−0.0023 (5)
O1C	0.0213 (5)	0.0235 (5)	0.0308 (5)	0.0020 (4)	0.0087 (4)	0.0019 (4)
C2C	0.0239 (6)	0.0280 (7)	0.0299 (7)	−0.0005 (5)	0.0102 (5)	−0.0009 (6)
C3C	0.0305 (7)	0.0286 (7)	0.0294 (7)	−0.0041 (6)	0.0112 (6)	0.0022 (6)
C4C	0.0280 (7)	0.0220 (7)	0.0256 (7)	−0.0023 (5)	0.0010 (5)	−0.0012 (5)
C5C	0.0226 (6)	0.0247 (7)	0.0327 (7)	0.0007 (5)	0.0062 (5)	−0.0033 (6)
C6C	0.0216 (6)	0.0242 (7)	0.0296 (7)	−0.0035 (5)	0.0082 (5)	−0.0012 (5)
C7C	0.0330 (7)	0.0228 (7)	0.0308 (8)	−0.0019 (6)	0.0004 (6)	0.0013 (6)
C8C	0.0243 (6)	0.0218 (7)	0.0264 (7)	0.0023 (5)	0.0035 (5)	0.0013 (5)
N2C	0.0193 (5)	0.0217 (6)	0.0241 (6)	0.0009 (4)	0.0077 (4)	0.0005 (4)
C1D	0.0234 (6)	0.0257 (7)	0.0280 (7)	0.0014 (5)	0.0079 (5)	−0.0034 (5)
O1D	0.0234 (5)	0.0297 (6)	0.0393 (6)	0.0046 (4)	0.0006 (4)	−0.0108 (5)
C2D	0.0248 (7)	0.0302 (8)	0.0280 (7)	0.0032 (5)	0.0034 (5)	−0.0025 (6)
C3D	0.0299 (7)	0.0320 (8)	0.0290 (7)	−0.0017 (6)	0.0035 (6)	−0.0060 (6)
C4D	0.0308 (7)	0.0266 (7)	0.0286 (7)	−0.0005 (5)	0.0140 (6)	−0.0005 (6)
C5D	0.0275 (7)	0.0285 (8)	0.0385 (8)	0.0049 (6)	0.0054 (6)	−0.0014 (6)
C6D	0.0245 (7)	0.0312 (8)	0.0373 (8)	0.0025 (6)	−0.0001 (6)	−0.0072 (6)
C7D	0.0370 (8)	0.0260 (7)	0.0336 (8)	−0.0015 (6)	0.0176 (6)	−0.0025 (6)
C8D	0.0334 (7)	0.0270 (7)	0.0295 (7)	−0.0022 (6)	0.0149 (6)	−0.0043 (6)
N2D	0.0212 (5)	0.0255 (6)	0.0184 (5)	−0.0015 (4)	0.0056 (4)	−0.0009 (4)
N1E	0.0164 (5)	0.0318 (6)	0.0205 (5)	−0.0005 (4)	0.0050 (4)	−0.0004 (5)
C2E	0.0199 (6)	0.0343 (8)	0.0231 (6)	−0.0005 (5)	0.0073 (5)	0.0005 (6)
O2E	0.0209 (5)	0.0812 (9)	0.0212 (5)	−0.0023 (5)	0.0068 (4)	−0.0021 (5)
N3E	0.0167 (5)	0.0314 (6)	0.0231 (6)	0.0003 (4)	0.0059 (4)	0.0006 (5)
C4E	0.0190 (6)	0.0222 (6)	0.0239 (6)	0.0011 (5)	0.0057 (5)	−0.0004 (5)
O4E	0.0178 (5)	0.0506 (7)	0.0278 (5)	−0.0003 (4)	0.0033 (4)	−0.0037 (5)
C5E	0.0189 (6)	0.0237 (6)	0.0201 (6)	0.0022 (5)	0.0051 (5)	−0.0011 (5)
C6E	0.0200 (6)	0.0180 (6)	0.0231 (6)	0.0012 (4)	0.0066 (5)	0.0001 (5)
O6E	0.0200 (5)	0.0347 (6)	0.0248 (5)	0.0024 (4)	0.0086 (4)	−0.0009 (4)
C7E	0.0273 (7)	0.0312 (8)	0.0256 (7)	0.0052 (6)	0.0057 (5)	0.0062 (6)
C8E	0.0482 (10)	0.0264 (8)	0.0465 (10)	0.0065 (7)	0.0154 (8)	0.0090 (7)
C9E	0.0280 (7)	0.0271 (7)	0.0293 (7)	0.0014 (5)	0.0041 (6)	−0.0069 (6)
C10E	0.0462 (10)	0.0233 (8)	0.0489 (10)	0.0005 (7)	0.0042 (8)	−0.0030 (7)
N1F	0.0199 (5)	0.0388 (7)	0.0151 (5)	0.0046 (5)	0.0054 (4)	−0.0004 (5)
C2F	0.0188 (6)	0.0284 (7)	0.0193 (6)	0.0041 (5)	0.0058 (5)	0.0010 (5)
O2F	0.0195 (5)	0.0600 (7)	0.0186 (5)	0.0083 (4)	0.0030 (4)	−0.0025 (5)
N3F	0.0212 (5)	0.0289 (6)	0.0170 (5)	0.0009 (4)	0.0065 (4)	−0.0003 (4)
C4F	0.0227 (6)	0.0278 (7)	0.0184 (6)	−0.0023 (5)	0.0061 (5)	−0.0004 (5)
O4F	0.0318 (6)	0.0662 (8)	0.0177 (5)	−0.0044 (5)	0.0080 (4)	−0.0053 (5)
C5F	0.0195 (6)	0.0295 (7)	0.0173 (6)	−0.0012 (5)	0.0037 (5)	−0.0005 (5)
C6F	0.0212 (6)	0.0280 (7)	0.0189 (6)	0.0006 (5)	0.0051 (5)	0.0005 (5)
O6F	0.0213 (5)	0.0551 (7)	0.0256 (5)	0.0007 (4)	0.0099 (4)	−0.0023 (5)
C7F	0.0268 (7)	0.0341 (8)	0.0248 (7)	0.0030 (6)	0.0020 (5)	0.0029 (6)
C8F	0.0469 (10)	0.0330 (9)	0.0478 (10)	0.0009 (7)	0.0074 (8)	0.0071 (8)
C9F	0.0267 (7)	0.0328 (8)	0.0334 (8)	−0.0075 (6)	0.0089 (6)	−0.0079 (6)
C10F	0.0459 (10)	0.0297 (9)	0.0639 (12)	−0.0052 (7)	0.0169 (9)	0.0011 (8)
N1G	0.0198 (5)	0.0344 (6)	0.0148 (5)	0.0048 (4)	0.0048 (4)	0.0002 (4)
C2G	0.0191 (6)	0.0230 (6)	0.0193 (6)	0.0026 (5)	0.0053 (5)	−0.0010 (5)
O2G	0.0211 (5)	0.0503 (7)	0.0183 (5)	0.0098 (4)	0.0037 (4)	−0.0010 (4)
N3G	0.0207 (5)	0.0285 (6)	0.0170 (5)	−0.0020 (4)	0.0065 (4)	−0.0023 (4)
C4G	0.0229 (6)	0.0356 (8)	0.0172 (6)	−0.0059 (5)	0.0059 (5)	−0.0026 (5)
O4G	0.0299 (6)	0.1033 (11)	0.0164 (5)	−0.0061 (6)	0.0068 (4)	−0.0037 (6)
C5G	0.0196 (6)	0.0285 (7)	0.0176 (6)	−0.0015 (5)	0.0034 (5)	0.0013 (5)
C6G	0.0201 (6)	0.0252 (7)	0.0187 (6)	0.0000 (5)	0.0049 (5)	0.0008 (5)
O6G	0.0202 (5)	0.0485 (7)	0.0245 (5)	0.0023 (4)	0.0088 (4)	0.0025 (4)
C7G	0.0376 (8)	0.0303 (8)	0.0259 (7)	0.0015 (6)	0.0029 (6)	0.0054 (6)
C8G	0.0636 (12)	0.0278 (9)	0.0468 (11)	−0.0062 (8)	0.0023 (9)	0.0036 (8)
C9G	0.0219 (6)	0.0327 (8)	0.0250 (7)	−0.0046 (5)	0.0023 (5)	−0.0026 (6)
C10G	0.0410 (9)	0.0302 (8)	0.0417 (9)	−0.0086 (7)	0.0047 (7)	−0.0009 (7)
N1H	0.0160 (5)	0.0314 (6)	0.0210 (5)	0.0008 (4)	0.0055 (4)	0.0006 (5)
C2H	0.0189 (6)	0.0263 (7)	0.0234 (6)	−0.0009 (5)	0.0073 (5)	−0.0008 (5)
O2H	0.0214 (5)	0.0552 (7)	0.0214 (5)	−0.0007 (4)	0.0063 (4)	0.0034 (5)
N3H	0.0175 (5)	0.0263 (6)	0.0222 (5)	0.0003 (4)	0.0065 (4)	0.0000 (4)
C4H	0.0179 (6)	0.0188 (6)	0.0250 (6)	0.0001 (4)	0.0054 (5)	−0.0020 (5)
O4H	0.0171 (4)	0.0387 (6)	0.0273 (5)	0.0004 (4)	0.0029 (4)	−0.0006 (4)
C5H	0.0191 (6)	0.0254 (7)	0.0209 (6)	0.0018 (5)	0.0057 (5)	0.0021 (5)
C6H	0.0190 (6)	0.0174 (6)	0.0234 (6)	0.0006 (4)	0.0066 (5)	−0.0004 (5)
O6H	0.0201 (4)	0.0333 (5)	0.0254 (5)	0.0023 (4)	0.0099 (4)	0.0006 (4)
C7H	0.0274 (7)	0.0315 (8)	0.0415 (9)	0.0060 (6)	0.0114 (6)	0.0140 (7)
C8H	0.0481 (10)	0.0241 (8)	0.0715 (13)	0.0004 (7)	0.0296 (9)	0.0038 (8)
C9H	0.0260 (7)	0.0412 (9)	0.0221 (7)	0.0022 (6)	0.0036 (5)	−0.0064 (6)
C10H	0.0401 (9)	0.0327 (9)	0.0451 (10)	−0.0023 (7)	0.0112 (7)	−0.0150 (7)
C11	0.0331 (8)	0.0361 (9)	0.0547 (11)	−0.0014 (7)	0.0080 (8)	0.0103 (8)
Cl11	0.0598 (12)	0.0324 (7)	0.0420 (10)	−0.0006 (7)	0.0113 (8)	0.0002 (5)
Cl12	0.0399 (13)	0.0564 (11)	0.0517 (14)	−0.0184 (7)	−0.0084 (8)	0.0231 (11)
Cl13	0.0512 (3)	0.0396 (2)	0.0446 (2)	0.00298 (18)	0.00756 (19)	−0.00324 (18)
Cl14	0.104 (5)	0.0395 (13)	0.069 (3)	−0.010 (2)	−0.012 (2)	−0.0033 (17)
Cl15	0.085 (4)	0.074 (3)	0.095 (4)	−0.023 (2)	−0.025 (3)	0.055 (3)
C22	0.0366 (8)	0.0352 (9)	0.0373 (9)	−0.0032 (7)	0.0039 (7)	−0.0081 (7)
Cl21	0.0527 (7)	0.0482 (8)	0.0662 (13)	0.0167 (6)	−0.0027 (6)	−0.0112 (7)
Cl22	0.0415 (9)	0.0293 (8)	0.0554 (11)	−0.0054 (5)	−0.0010 (8)	−0.0049 (7)
Cl23	0.0599 (13)	0.0738 (14)	0.0449 (8)	−0.0202 (7)	0.0186 (9)	−0.0190 (9)
Cl24	0.0532 (16)	0.0390 (16)	0.139 (7)	0.0054 (11)	−0.014 (3)	−0.034 (3)
Cl25	0.087 (4)	0.041 (2)	0.062 (2)	−0.0163 (17)	0.027 (2)	−0.0123 (14)
Cl26	0.127 (5)	0.065 (2)	0.072 (2)	−0.025 (3)	0.063 (3)	0.0044 (19)
C33	0.0365 (9)	0.0376 (9)	0.0439 (10)	−0.0040 (7)	0.0064 (7)	0.0014 (7)
Cl31	0.0506 (16)	0.0271 (15)	0.0533 (15)	−0.0002 (13)	0.0112 (12)	0.0012 (14)
Cl32	0.0514 (3)	0.0452 (3)	0.0437 (2)	0.00174 (19)	0.00272 (19)	0.01060 (19)
Cl33	0.0572 (18)	0.0398 (13)	0.0459 (10)	0.0046 (10)	0.0095 (10)	−0.0104 (8)
Cl34	0.0451 (15)	0.052 (2)	0.0542 (16)	0.0164 (15)	0.0038 (12)	−0.0186 (16)
Cl36	0.074 (3)	0.0436 (9)	0.0338 (8)	−0.0003 (15)	0.0015 (12)	−0.0050 (6)
C44	0.0343 (8)	0.0443 (10)	0.0387 (9)	0.0026 (7)	0.0053 (7)	−0.0114 (8)
Cl41	0.0485 (11)	0.0392 (6)	0.0589 (9)	−0.0099 (4)	−0.0040 (5)	0.0017 (6)
Cl42	0.0782 (14)	0.0988 (14)	0.0898 (15)	−0.0125 (10)	0.0578 (13)	−0.0206 (11)
Cl43	0.0395 (5)	0.0448 (6)	0.0867 (19)	0.0124 (4)	0.0043 (9)	−0.0140 (10)
Cl44	0.134 (4)	0.0435 (18)	0.073 (3)	−0.0088 (18)	0.008 (2)	−0.0180 (16)
Cl45	0.0527 (18)	0.133 (5)	0.0488 (16)	0.010 (2)	0.0185 (13)	0.0165 (19)
Cl46	0.0528 (12)	0.0407 (13)	0.074 (3)	0.0042 (10)	0.0005 (16)	−0.0214 (17)

Geometric parameters (Å, º) top

C1A—O1A	1.3674 (17)	C9E—C10E	1.521 (2)
C1A—C2A	1.3915 (19)	C9E—H9E1	0.9900
C1A—C6A	1.3924 (19)	C9E—H9E2	0.9900
O1A—H1A	0.787 (19)	C10E—H10E	0.975 (9)
C2A—C3A	1.390 (2)	C10E—H11E	0.977 (9)
C2A—H2A	0.9500	C10E—H12E	0.974 (9)
C3A—C4A	1.395 (2)	N1F—C6F	1.3542 (17)
C3A—H3A	0.9500	N1F—C2F	1.3881 (16)
C4A—C5A	1.390 (2)	N1F—H1F	0.883 (9)
C4A—C7A	1.511 (2)	C2F—O2F	1.2496 (16)
C5A—C6A	1.386 (2)	C2F—N3F	1.3343 (16)
C5A—H5A	0.9500	N3F—C4F	1.3521 (17)
C6A—H6A	0.9500	C4F—O4F	1.2306 (16)
C7A—C8A	1.5231 (19)	C4F—C5F	1.5369 (18)
C7A—H7A1	0.9900	C5F—C6F	1.5183 (18)
C7A—H7A2	0.9900	C5F—C7F	1.5431 (19)
C8A—N2A	1.4874 (18)	C5F—C9F	1.5462 (19)
C8A—H8A1	0.9900	C6F—O6F	1.2235 (16)
C8A—H8A2	0.9900	C7F—C8F	1.525 (2)
N2A—H11A	0.905 (9)	C7F—H7F1	0.9900
N2A—H12A	0.905 (9)	C7F—H7F2	0.9900
N2A—H13A	0.909 (9)	C8F—H81F	0.980 (9)
C1B—O1B	1.3615 (17)	C8F—H83F	0.979 (9)
C1B—C6B	1.3887 (19)	C8F—H82F	0.981 (9)
C1B—C2B	1.3973 (19)	C9F—C10F	1.521 (2)
O1B—H1B	0.804 (18)	C9F—H9F1	0.9900
C2B—C3B	1.390 (2)	C9F—H9F2	0.9900
C2B—H2B	0.9500	C10F—H10F	0.983 (9)
C3B—C4B	1.394 (2)	C10F—H11F	0.977 (9)
C3B—H3B	0.9500	C10F—H12F	0.981 (9)
C4B—C5B	1.391 (2)	N1G—C6G	1.3565 (16)
C4B—C7B	1.514 (2)	N1G—C2G	1.3889 (16)
C5B—C6B	1.391 (2)	N1G—H1G	0.885 (9)
C5B—H5B	0.9500	C2G—O2G	1.2521 (15)
C6B—H6B	0.9500	C2G—N3G	1.3299 (16)
C7B—C8B	1.514 (2)	N3G—C4G	1.3558 (17)
C7B—H7B1	0.9900	C4G—O4G	1.2287 (16)
C7B—H7B2	0.9900	C4G—C5G	1.5328 (19)
C8B—N2B	1.4916 (18)	C5G—C6G	1.5173 (18)
C8B—H8B1	0.9900	C5G—C9G	1.5445 (19)
C8B—H8B2	0.9900	C5G—C7G	1.547 (2)
N2B—H11B	0.908 (9)	C6G—O6G	1.2239 (15)
N2B—H12B	0.916 (9)	C7G—C8G	1.526 (2)
N2B—H13B	0.909 (9)	C7G—H7G1	0.9900
C1C—O1C	1.3631 (16)	C7G—H7G2	0.9900
C1C—C2C	1.3939 (19)	C8G—H83G	0.977 (9)
C1C—C6C	1.3953 (18)	C8G—H82G	0.976 (9)
O1C—H1C	0.802 (18)	C8G—H81G	0.974 (9)
C2C—C3C	1.389 (2)	C9G—C10G	1.520 (2)
C2C—H2C	0.9500	C9G—H9G1	0.9900
C3C—C4C	1.394 (2)	C9G—H9G2	0.9900
C3C—H3C	0.9500	C10G—H10G	0.981 (9)
C4C—C5C	1.393 (2)	C10G—H11G	0.979 (9)
C4C—C7C	1.508 (2)	C10G—H12G	0.985 (9)
C5C—C6C	1.389 (2)	N1H—C6H	1.3532 (17)
C5C—H5C	0.9500	N1H—C2H	1.4031 (16)
C6C—H6C	0.9500	N1H—H1H	0.875 (9)
C7C—C8C	1.5190 (19)	C2H—O2H	1.2383 (16)
C7C—H7C1	0.9900	C2H—N3H	1.3463 (17)
C7C—H7C2	0.9900	N3H—C4H	1.3543 (17)
C8C—N2C	1.4871 (17)	C4H—O4H	1.2354 (15)
C8C—H8C1	0.9900	C4H—C5H	1.5431 (18)
C8C—H8C2	0.9900	C5H—C6H	1.5139 (18)
N2C—H11C	0.907 (9)	C5H—C9H	1.5427 (19)
N2C—H12C	0.911 (9)	C5H—C7H	1.549 (2)
N2C—H13C	0.912 (9)	C6H—O6H	1.2339 (15)
C1D—O1D	1.3705 (17)	C7H—C8H	1.520 (3)
C1D—C6D	1.389 (2)	C7H—H7H1	0.9900
C1D—C2D	1.3906 (19)	C7H—H7H2	0.9900
O1D—H1D	0.812 (19)	C8H—H83H	0.982 (9)
C2D—C3D	1.390 (2)	C8H—H81H	0.984 (9)
C2D—H2D	0.9500	C8H—H82H	0.980 (9)
C3D—C4D	1.396 (2)	C9H—C10H	1.522 (2)
C3D—H3D	0.9500	C9H—H9H1	0.9900
C4D—C5D	1.390 (2)	C9H—H9H2	0.9900
C4D—C7D	1.511 (2)	C10H—H10H	0.985 (9)
C5D—C6D	1.386 (2)	C10H—H11H	0.986 (9)
C5D—H5D	0.9500	C10H—H12H	0.982 (9)
C6D—H6D	0.9500	C11—Cl11	1.736 (4)
C7D—C8D	1.521 (2)	C11—Cl15	1.742 (7)
C7D—H7D1	0.9900	C11—Cl13	1.7604 (19)
C7D—H7D2	0.9900	C11—Cl12	1.772 (4)
C8D—N2D	1.4904 (18)	C11—Cl14	1.781 (11)
C8D—H8D1	0.9900	C11—H11	0.92 (2)
C8D—H8D2	0.9900	C22—Cl26	1.722 (6)
N2D—H11D	0.903 (9)	C22—Cl25	1.727 (8)
N2D—H12D	0.900 (9)	C22—Cl21	1.751 (4)
N2D—H13D	0.905 (9)	C22—Cl24	1.762 (8)
N1E—C6E	1.3531 (17)	C22—Cl23	1.769 (4)
N1E—C2E	1.4009 (17)	C22—Cl22	1.770 (4)
N1E—H1E	0.876 (9)	C22—H22	0.93 (2)
C2E—O2E	1.2407 (17)	C33—Cl33	1.700 (6)
C2E—N3E	1.3438 (17)	C33—Cl34	1.742 (5)
N3E—C4E	1.3486 (17)	C33—Cl32	1.7562 (18)
C4E—O4E	1.2339 (16)	C33—Cl31	1.776 (5)
C4E—C5E	1.5393 (18)	C33—Cl36	1.818 (9)
C5E—C6E	1.5168 (18)	C33—H33	0.96 (2)
C5E—C7E	1.5429 (19)	C44—Cl44	1.657 (8)
C5E—C9E	1.5517 (19)	C44—Cl42	1.697 (4)
C6E—O6E	1.2317 (15)	C44—Cl43	1.724 (3)
C7E—C8E	1.524 (2)	C44—Cl41	1.795 (3)
C7E—H7E1	0.9900	C44—Cl46	1.824 (7)
C7E—H7E2	0.9900	C44—Cl45	1.848 (8)
C8E—H81E	0.981 (9)	C44—H44	0.97 (2)
C8E—H82E	0.985 (9)	Cl43—Cl46	0.506 (7)
C8E—H83E	0.982 (9)

O1A—C1A—C2A	122.37 (12)	C2F—N3F—C4F	119.78 (11)
O1A—C1A—C6A	117.80 (12)	O4F—C4F—N3F	119.35 (12)
C2A—C1A—C6A	119.83 (13)	O4F—C4F—C5F	117.79 (12)
C1A—O1A—H1A	112.5 (14)	N3F—C4F—C5F	122.84 (11)
C3A—C2A—C1A	119.49 (13)	C6F—C5F—C4F	113.04 (11)
C3A—C2A—H2A	120.3	C6F—C5F—C7F	108.38 (11)
C1A—C2A—H2A	120.3	C4F—C5F—C7F	110.14 (11)
C2A—C3A—C4A	121.54 (13)	C6F—C5F—C9F	107.62 (11)
C2A—C3A—H3A	119.2	C4F—C5F—C9F	108.89 (11)
C4A—C3A—H3A	119.2	C7F—C5F—C9F	108.65 (11)
C5A—C4A—C3A	117.85 (13)	O6F—C6F—N1F	120.90 (12)
C5A—C4A—C7A	121.28 (13)	O6F—C6F—C5F	122.01 (12)
C3A—C4A—C7A	120.84 (13)	N1F—C6F—C5F	117.09 (11)
C6A—C5A—C4A	121.59 (13)	C8F—C7F—C5F	114.31 (12)
C6A—C5A—H5A	119.2	C8F—C7F—H7F1	108.7
C4A—C5A—H5A	119.2	C5F—C7F—H7F1	108.7
C5A—C6A—C1A	119.70 (13)	C8F—C7F—H7F2	108.7
C5A—C6A—H6A	120.2	C5F—C7F—H7F2	108.7
C1A—C6A—H6A	120.2	H7F1—C7F—H7F2	107.6
C4A—C7A—C8A	110.47 (11)	C7F—C8F—H81F	109.7 (14)
C4A—C7A—H7A1	109.6	C7F—C8F—H83F	112.2 (13)
C8A—C7A—H7A1	109.6	H81F—C8F—H83F	110.9 (18)
C4A—C7A—H7A2	109.6	C7F—C8F—H82F	110.0 (13)
C8A—C7A—H7A2	109.6	H81F—C8F—H82F	107.2 (18)
H7A1—C7A—H7A2	108.1	H83F—C8F—H82F	106.7 (19)
N2A—C8A—C7A	112.32 (11)	C10F—C9F—C5F	113.99 (13)
N2A—C8A—H8A1	109.1	C10F—C9F—H9F1	108.8
C7A—C8A—H8A1	109.1	C5F—C9F—H9F1	108.8
N2A—C8A—H8A2	109.1	C10F—C9F—H9F2	108.8
C7A—C8A—H8A2	109.1	C5F—C9F—H9F2	108.8
H8A1—C8A—H8A2	107.9	H9F1—C9F—H9F2	107.6
C8A—N2A—H11A	110.2 (11)	C9F—C10F—H10F	111.0 (14)
C8A—N2A—H12A	107.5 (11)	C9F—C10F—H11F	111.2 (14)
H11A—N2A—H12A	114.3 (15)	H10F—C10F—H11F	109.8 (19)
C8A—N2A—H13A	105.9 (11)	C9F—C10F—H12F	113.0 (13)
H11A—N2A—H13A	108.4 (15)	H10F—C10F—H12F	106.2 (19)
H12A—N2A—H13A	110.2 (15)	H11F—C10F—H12F	105.3 (19)
O1B—C1B—C6B	117.35 (12)	C6G—N1G—C2G	124.87 (11)
O1B—C1B—C2B	123.26 (12)	C6G—N1G—H1G	118.7 (11)
C6B—C1B—C2B	119.40 (13)	C2G—N1G—H1G	116.4 (11)
C1B—O1B—H1B	111.3 (12)	O2G—C2G—N3G	121.45 (11)
C3B—C2B—C1B	119.52 (14)	O2G—C2G—N1G	116.20 (11)
C3B—C2B—H2B	120.2	N3G—C2G—N1G	122.34 (11)
C1B—C2B—H2B	120.2	C2G—N3G—C4G	119.60 (11)
C2B—C3B—C4B	121.80 (14)	O4G—C4G—N3G	118.99 (12)
C2B—C3B—H3B	119.1	O4G—C4G—C5G	118.07 (12)
C4B—C3B—H3B	119.1	N3G—C4G—C5G	122.93 (11)
C5B—C4B—C3B	117.75 (14)	C6G—C5G—C4G	113.03 (11)
C5B—C4B—C7B	121.52 (14)	C6G—C5G—C9G	108.23 (11)
C3B—C4B—C7B	120.72 (14)	C4G—C5G—C9G	108.95 (11)
C4B—C5B—C6B	121.32 (14)	C6G—C5G—C7G	108.46 (11)
C4B—C5B—H5B	119.3	C4G—C5G—C7G	109.12 (11)
C6B—C5B—H5B	119.3	C9G—C5G—C7G	108.99 (11)
C1B—C6B—C5B	120.20 (13)	O6G—C6G—N1G	120.79 (12)
C1B—C6B—H6B	119.9	O6G—C6G—C5G	122.15 (12)
C5B—C6B—H6B	119.9	N1G—C6G—C5G	117.06 (11)
C4B—C7B—C8B	110.67 (12)	C8G—C7G—C5G	114.12 (13)
C4B—C7B—H7B1	109.5	C8G—C7G—H7G1	108.7
C8B—C7B—H7B1	109.5	C5G—C7G—H7G1	108.7
C4B—C7B—H7B2	109.5	C8G—C7G—H7G2	108.7
C8B—C7B—H7B2	109.5	C5G—C7G—H7G2	108.7
H7B1—C7B—H7B2	108.1	H7G1—C7G—H7G2	107.6
N2B—C8B—C7B	110.42 (11)	C7G—C8G—H83G	110.1 (14)
N2B—C8B—H8B1	109.6	C7G—C8G—H82G	114.6 (14)
C7B—C8B—H8B1	109.6	H83G—C8G—H82G	107 (2)
N2B—C8B—H8B2	109.6	C7G—C8G—H81G	110.7 (14)
C7B—C8B—H8B2	109.6	H83G—C8G—H81G	108.8 (19)
H8B1—C8B—H8B2	108.1	H82G—C8G—H81G	105.3 (19)
C8B—N2B—H11B	103.0 (11)	C10G—C9G—C5G	113.97 (12)
C8B—N2B—H12B	110.4 (11)	C10G—C9G—H9G1	108.8
H11B—N2B—H12B	111.4 (15)	C5G—C9G—H9G1	108.8
C8B—N2B—H13B	111.7 (11)	C10G—C9G—H9G2	108.8
H11B—N2B—H13B	110.4 (15)	C5G—C9G—H9G2	108.8
H12B—N2B—H13B	109.7 (15)	H9G1—C9G—H9G2	107.7
O1C—C1C—C2C	122.87 (12)	C9G—C10G—H10G	109.3 (12)
O1C—C1C—C6C	117.72 (12)	C9G—C10G—H11G	110.5 (13)
C2C—C1C—C6C	119.41 (13)	H10G—C10G—H11G	108.2 (17)
C1C—O1C—H1C	109.8 (13)	C9G—C10G—H12G	110.1 (13)
C3C—C2C—C1C	119.88 (13)	H10G—C10G—H12G	108.9 (17)
C3C—C2C—H2C	120.1	H11G—C10G—H12G	109.9 (17)
C1C—C2C—H2C	120.1	C6H—N1H—C2H	124.62 (11)
C2C—C3C—C4C	121.56 (13)	C6H—N1H—H1H	120.9 (11)
C2C—C3C—H3C	119.2	C2H—N1H—H1H	114.4 (11)
C4C—C3C—H3C	119.2	O2H—C2H—N3H	121.63 (12)
C5C—C4C—C3C	117.73 (13)	O2H—C2H—N1H	116.81 (12)
C5C—C4C—C7C	121.04 (13)	N3H—C2H—N1H	121.57 (12)
C3C—C4C—C7C	121.17 (13)	C2H—N3H—C4H	120.51 (11)
C6C—C5C—C4C	121.64 (13)	O4H—C4H—N3H	121.31 (12)
C6C—C5C—H5C	119.2	O4H—C4H—C5H	116.78 (12)
C4C—C5C—H5C	119.2	N3H—C4H—C5H	121.91 (11)
C5C—C6C—C1C	119.79 (13)	C6H—C5H—C9H	108.78 (11)
C5C—C6C—H6C	120.1	C6H—C5H—C4H	113.65 (11)
C1C—C6C—H6C	120.1	C9H—C5H—C4H	108.67 (11)
C4C—C7C—C8C	110.71 (12)	C6H—C5H—C7H	107.62 (11)
C4C—C7C—H7C1	109.5	C9H—C5H—C7H	108.95 (12)
C8C—C7C—H7C1	109.5	C4H—C5H—C7H	109.08 (11)
C4C—C7C—H7C2	109.5	O6H—C6H—N1H	121.25 (12)
C8C—C7C—H7C2	109.5	O6H—C6H—C5H	121.23 (12)
H7C1—C7C—H7C2	108.1	N1H—C6H—C5H	117.51 (11)
N2C—C8C—C7C	110.81 (11)	C8H—C7H—C5H	114.56 (13)
N2C—C8C—H8C1	109.5	C8H—C7H—H7H1	108.6
C7C—C8C—H8C1	109.5	C5H—C7H—H7H1	108.6
N2C—C8C—H8C2	109.5	C8H—C7H—H7H2	108.6
C7C—C8C—H8C2	109.5	C5H—C7H—H7H2	108.6
H8C1—C8C—H8C2	108.1	H7H1—C7H—H7H2	107.6
C8C—N2C—H11C	103.4 (11)	C7H—C8H—H83H	111.5 (14)
C8C—N2C—H12C	109.2 (11)	C7H—C8H—H81H	113.5 (13)
H11C—N2C—H12C	110.6 (15)	H83H—C8H—H81H	105.6 (19)
C8C—N2C—H13C	108.9 (11)	C7H—C8H—H82H	113.9 (13)
H11C—N2C—H13C	112.1 (15)	H83H—C8H—H82H	108.1 (18)
H12C—N2C—H13C	112.1 (15)	H81H—C8H—H82H	103.6 (18)
O1D—C1D—C6D	117.86 (13)	C10H—C9H—C5H	114.22 (12)
O1D—C1D—C2D	122.28 (13)	C10H—C9H—H9H1	108.7
C6D—C1D—C2D	119.86 (13)	C5H—C9H—H9H1	108.7
C1D—O1D—H1D	112.1 (13)	C10H—C9H—H9H2	108.7
C3D—C2D—C1D	119.40 (13)	C5H—C9H—H9H2	108.7
C3D—C2D—H2D	120.3	H9H1—C9H—H9H2	107.6
C1D—C2D—H2D	120.3	C9H—C10H—H10H	112.1 (13)
C2D—C3D—C4D	121.59 (13)	C9H—C10H—H11H	111.3 (13)
C2D—C3D—H3D	119.2	H10H—C10H—H11H	109.4 (17)
C4D—C3D—H3D	119.2	C9H—C10H—H12H	110.7 (13)
C5D—C4D—C3D	117.73 (13)	H10H—C10H—H12H	105.8 (17)
C5D—C4D—C7D	121.11 (14)	H11H—C10H—H12H	107.2 (17)
C3D—C4D—C7D	121.05 (13)	Cl11—C11—Cl15	116.0 (5)
C6D—C5D—C4D	121.52 (14)	Cl11—C11—Cl13	113.08 (17)
C6D—C5D—H5D	119.2	Cl15—C11—Cl13	107.8 (3)
C4D—C5D—H5D	119.2	Cl11—C11—Cl12	110.8 (2)
C5D—C6D—C1D	119.87 (14)	Cl15—C11—Cl12	5.5 (5)
C5D—C6D—H6D	120.1	Cl13—C11—Cl12	109.72 (13)
C1D—C6D—H6D	120.1	Cl11—C11—Cl14	10.9 (9)
C4D—C7D—C8D	109.64 (12)	Cl15—C11—Cl14	110.3 (4)
C4D—C7D—H7D1	109.7	Cl13—C11—Cl14	108.1 (5)
C8D—C7D—H7D1	109.7	Cl12—C11—Cl14	104.9 (5)
C4D—C7D—H7D2	109.7	Cl11—C11—H11	102.4 (13)
C8D—C7D—H7D2	109.7	Cl15—C11—H11	106.6 (13)
H7D1—C7D—H7D2	108.2	Cl13—C11—H11	110.6 (12)
N2D—C8D—C7D	113.03 (11)	Cl12—C11—H11	110.1 (12)
N2D—C8D—H8D1	109.0	Cl14—C11—H11	113.3 (16)
C7D—C8D—H8D1	109.0	Cl26—C22—Cl25	108.9 (4)
N2D—C8D—H8D2	109.0	Cl26—C22—Cl21	107.4 (6)
C7D—C8D—H8D2	109.0	Cl25—C22—Cl21	113.1 (3)
H8D1—C8D—H8D2	107.8	Cl26—C22—Cl24	94.5 (13)
C8D—N2D—H11D	108.0 (11)	Cl25—C22—Cl24	113.2 (3)
C8D—N2D—H12D	107.2 (11)	Cl21—C22—Cl24	14.4 (8)
H11D—N2D—H12D	108.7 (15)	Cl26—C22—Cl23	10.1 (6)
C8D—N2D—H13D	111.5 (11)	Cl25—C22—Cl23	105.8 (4)
H11D—N2D—H13D	106.8 (15)	Cl21—C22—Cl23	117.1 (2)
H12D—N2D—H13D	114.4 (16)	Cl24—C22—Cl23	104.4 (8)
C6E—N1E—C2E	124.65 (11)	Cl26—C22—Cl22	115.1 (3)
C6E—N1E—H1E	122.7 (11)	Cl25—C22—Cl22	6.1 (5)
C2E—N1E—H1E	112.6 (11)	Cl21—C22—Cl22	109.69 (19)
O2E—C2E—N3E	121.74 (12)	Cl24—C22—Cl22	111.3 (2)
O2E—C2E—N1E	116.83 (12)	Cl23—C22—Cl22	111.9 (2)
N3E—C2E—N1E	121.43 (12)	Cl26—C22—H22	111.9 (13)
C2E—N3E—C4E	120.75 (11)	Cl25—C22—H22	110.5 (13)
O4E—C4E—N3E	121.33 (12)	Cl21—C22—H22	104.9 (12)
O4E—C4E—C5E	116.60 (12)	Cl24—C22—H22	116.6 (14)
N3E—C4E—C5E	122.06 (11)	Cl23—C22—H22	105.1 (12)
C6E—C5E—C4E	113.49 (11)	Cl22—C22—H22	107.4 (12)
C6E—C5E—C7E	109.00 (11)	Cl33—C33—Cl34	114.3 (3)
C4E—C5E—C7E	109.69 (11)	Cl33—C33—Cl32	113.7 (2)
C6E—C5E—C9E	107.59 (10)	Cl34—C33—Cl32	110.0 (2)
C4E—C5E—C9E	108.16 (11)	Cl33—C33—Cl31	110.6 (3)
C7E—C5E—C9E	108.79 (11)	Cl34—C33—Cl31	4.2 (4)
O6E—C6E—N1E	121.30 (12)	Cl32—C33—Cl31	110.9 (2)
O6E—C6E—C5E	121.16 (12)	Cl33—C33—Cl36	11.7 (2)
N1E—C6E—C5E	117.54 (11)	Cl34—C33—Cl36	109.6 (3)
C8E—C7E—C5E	114.38 (12)	Cl32—C33—Cl36	107.4 (3)
C8E—C7E—H7E1	108.7	Cl31—C33—Cl36	105.6 (3)
C5E—C7E—H7E1	108.7	Cl33—C33—H33	101.7 (12)
C8E—C7E—H7E2	108.7	Cl34—C33—H33	106.9 (12)
C5E—C7E—H7E2	108.7	Cl32—C33—H33	109.5 (12)
H7E1—C7E—H7E2	107.6	Cl31—C33—H33	109.9 (12)
C7E—C8E—H81E	110.1 (13)	Cl36—C33—H33	113.4 (12)
C7E—C8E—H82E	111.1 (13)	Cl44—C44—Cl42	100.2 (4)
H81E—C8E—H82E	110.1 (18)	Cl44—C44—Cl43	112.4 (3)
C7E—C8E—H83E	110.1 (13)	Cl42—C44—Cl43	116.8 (3)
H81E—C8E—H83E	109.4 (17)	Cl44—C44—Cl41	10.2 (5)
H82E—C8E—H83E	105.9 (17)	Cl42—C44—Cl41	109.9 (2)
C10E—C9E—C5E	114.14 (12)	Cl43—C44—Cl41	109.02 (16)
C10E—C9E—H9E1	108.7	Cl44—C44—Cl46	112.7 (3)
C5E—C9E—H9E1	108.7	Cl42—C44—Cl46	101.6 (4)
C10E—C9E—H9E2	108.7	Cl43—C44—Cl46	16.09 (19)
C5E—C9E—H9E2	108.7	Cl41—C44—Cl46	112.3 (2)
H9E1—C9E—H9E2	107.6	Cl44—C44—Cl45	110.0 (4)
C9E—C10E—H10E	112.5 (13)	Cl42—C44—Cl45	9.9 (4)
C9E—C10E—H11E	112.5 (13)	Cl43—C44—Cl45	111.8 (4)
H10E—C10E—H11E	105.7 (18)	Cl41—C44—Cl45	119.7 (4)
C9E—C10E—H12E	109.7 (13)	Cl46—C44—Cl45	97.7 (5)
H10E—C10E—H12E	105.9 (18)	Cl44—C44—H44	114.2 (12)
H11E—C10E—H12E	110.3 (18)	Cl42—C44—H44	109.0 (12)
C6F—N1F—C2F	125.07 (11)	Cl43—C44—H44	104.7 (12)
C6F—N1F—H1F	118.2 (11)	Cl41—C44—H44	106.9 (12)
C2F—N1F—H1F	116.6 (11)	Cl46—C44—H44	116.9 (12)
O2F—C2F—N3F	121.72 (12)	Cl45—C44—H44	103.4 (12)
O2F—C2F—N1F	116.14 (11)	Cl46—Cl43—C44	93.2 (9)
N3F—C2F—N1F	122.14 (11)	Cl43—Cl46—C44	70.7 (9)

O1A—C1A—C2A—C3A	179.65 (13)	C2F—N3F—C4F—O4F	179.77 (14)
C6A—C1A—C2A—C3A	−0.7 (2)	C2F—N3F—C4F—C5F	−1.4 (2)
C1A—C2A—C3A—C4A	0.0 (2)	O4F—C4F—C5F—C6F	−179.49 (13)
C2A—C3A—C4A—C5A	0.7 (2)	N3F—C4F—C5F—C6F	1.62 (19)
C2A—C3A—C4A—C7A	−177.23 (14)	O4F—C4F—C5F—C7F	−58.09 (17)
C3A—C4A—C5A—C6A	−0.8 (2)	N3F—C4F—C5F—C7F	123.02 (14)
C7A—C4A—C5A—C6A	177.17 (14)	O4F—C4F—C5F—C9F	60.96 (17)
C4A—C5A—C6A—C1A	0.1 (2)	N3F—C4F—C5F—C9F	−117.93 (14)
O1A—C1A—C6A—C5A	−179.68 (13)	C2F—N1F—C6F—O6F	178.39 (14)
C2A—C1A—C6A—C5A	0.6 (2)	C2F—N1F—C6F—C5F	−1.1 (2)
C5A—C4A—C7A—C8A	−100.10 (16)	C4F—C5F—C6F—O6F	−179.87 (13)
C3A—C4A—C7A—C8A	77.77 (18)	C7F—C5F—C6F—O6F	57.74 (17)
C4A—C7A—C8A—N2A	−179.25 (12)	C9F—C5F—C6F—O6F	−59.59 (17)
O1B—C1B—C2B—C3B	−178.68 (13)	C4F—C5F—C6F—N1F	−0.38 (18)
C6B—C1B—C2B—C3B	0.7 (2)	C7F—C5F—C6F—N1F	−122.76 (13)
C1B—C2B—C3B—C4B	0.1 (2)	C9F—C5F—C6F—N1F	119.90 (13)
C2B—C3B—C4B—C5B	−0.9 (2)	C6F—C5F—C7F—C8F	60.95 (16)
C2B—C3B—C4B—C7B	−179.56 (14)	C4F—C5F—C7F—C8F	−63.18 (16)
C3B—C4B—C5B—C6B	1.0 (2)	C9F—C5F—C7F—C8F	177.62 (13)
C7B—C4B—C5B—C6B	179.66 (14)	C6F—C5F—C9F—C10F	−62.62 (16)
O1B—C1B—C6B—C5B	178.83 (13)	C4F—C5F—C9F—C10F	60.24 (16)
C2B—C1B—C6B—C5B	−0.5 (2)	C7F—C5F—C9F—C10F	−179.78 (13)
C4B—C5B—C6B—C1B	−0.3 (2)	C6G—N1G—C2G—O2G	−178.14 (13)
C5B—C4B—C7B—C8B	−97.25 (17)	C6G—N1G—C2G—N3G	2.0 (2)
C3B—C4B—C7B—C8B	81.39 (18)	O2G—C2G—N3G—C4G	177.48 (13)
C4B—C7B—C8B—N2B	−172.05 (12)	N1G—C2G—N3G—C4G	−2.7 (2)
O1C—C1C—C2C—C3C	−179.55 (13)	C2G—N3G—C4G—O4G	−179.36 (14)
C6C—C1C—C2C—C3C	0.6 (2)	C2G—N3G—C4G—C5G	−0.4 (2)
C1C—C2C—C3C—C4C	−0.2 (2)	O4G—C4G—C5G—C6G	−177.27 (14)
C2C—C3C—C4C—C5C	0.0 (2)	N3G—C4G—C5G—C6G	3.77 (19)
C2C—C3C—C4C—C7C	177.28 (13)	O4G—C4G—C5G—C9G	−56.92 (18)
C3C—C4C—C5C—C6C	−0.2 (2)	N3G—C4G—C5G—C9G	124.11 (14)
C7C—C4C—C5C—C6C	−177.50 (13)	O4G—C4G—C5G—C7G	61.97 (18)
C4C—C5C—C6C—C1C	0.6 (2)	N3G—C4G—C5G—C7G	−117.00 (14)
O1C—C1C—C6C—C5C	179.33 (12)	C2G—N1G—C6G—O6G	−178.77 (13)
C2C—C1C—C6C—C5C	−0.8 (2)	C2G—N1G—C6G—C5G	1.8 (2)
C5C—C4C—C7C—C8C	94.81 (16)	C4G—C5G—C6G—O6G	176.32 (13)
C3C—C4C—C7C—C8C	−82.40 (17)	C9G—C5G—C6G—O6G	55.57 (17)
C4C—C7C—C8C—N2C	179.55 (12)	C7G—C5G—C6G—O6G	−62.54 (17)
O1D—C1D—C2D—C3D	−178.96 (14)	C4G—C5G—C6G—N1G	−4.23 (17)
C6D—C1D—C2D—C3D	1.7 (2)	C9G—C5G—C6G—N1G	−124.98 (13)
C1D—C2D—C3D—C4D	−0.5 (2)	C7G—C5G—C6G—N1G	116.91 (13)
C2D—C3D—C4D—C5D	−0.9 (2)	C6G—C5G—C7G—C8G	−60.26 (17)
C2D—C3D—C4D—C7D	175.41 (14)	C4G—C5G—C7G—C8G	63.26 (17)
C3D—C4D—C5D—C6D	1.0 (2)	C9G—C5G—C7G—C8G	−177.88 (14)
C7D—C4D—C5D—C6D	−175.28 (14)	C6G—C5G—C9G—C10G	61.31 (16)
C4D—C5D—C6D—C1D	0.2 (2)	C4G—C5G—C9G—C10G	−61.95 (16)
O1D—C1D—C6D—C5D	179.04 (14)	C7G—C5G—C9G—C10G	179.09 (13)
C2D—C1D—C6D—C5D	−1.6 (2)	C6H—N1H—C2H—O2H	179.33 (13)
C5D—C4D—C7D—C8D	92.05 (17)	C6H—N1H—C2H—N3H	−0.3 (2)
C3D—C4D—C7D—C8D	−84.15 (17)	O2H—C2H—N3H—C4H	178.00 (13)
C4D—C7D—C8D—N2D	−177.61 (12)	N1H—C2H—N3H—C4H	−2.4 (2)
C6E—N1E—C2E—O2E	−179.23 (14)	C2H—N3H—C4H—O4H	−178.52 (13)
C6E—N1E—C2E—N3E	0.9 (2)	C2H—N3H—C4H—C5H	0.61 (19)
O2E—C2E—N3E—C4E	−178.89 (14)	O4H—C4H—C5H—C6H	−177.53 (12)
N1E—C2E—N3E—C4E	1.0 (2)	N3H—C4H—C5H—C6H	3.31 (17)
C2E—N3E—C4E—O4E	178.34 (13)	O4H—C4H—C5H—C9H	−56.26 (15)
C2E—N3E—C4E—C5E	−2.9 (2)	N3H—C4H—C5H—C9H	124.57 (13)
O4E—C4E—C5E—C6E	−178.23 (12)	O4H—C4H—C5H—C7H	62.40 (16)
N3E—C4E—C5E—C6E	2.99 (18)	N3H—C4H—C5H—C7H	−116.77 (14)
O4E—C4E—C5E—C7E	−56.06 (16)	C2H—N1H—C6H—O6H	−176.41 (12)
N3E—C4E—C5E—C7E	125.17 (13)	C2H—N1H—C6H—C5H	4.45 (19)
O4E—C4E—C5E—C9E	62.46 (15)	C9H—C5H—C6H—O6H	54.09 (16)
N3E—C4E—C5E—C9E	−116.32 (14)	C4H—C5H—C6H—O6H	175.30 (12)
C2E—N1E—C6E—O6E	178.69 (13)	C7H—C5H—C6H—O6H	−63.81 (16)
C2E—N1E—C6E—C5E	−0.63 (19)	C9H—C5H—C6H—N1H	−126.77 (13)
C4E—C5E—C6E—O6E	179.51 (12)	C4H—C5H—C6H—N1H	−5.57 (17)
C7E—C5E—C6E—O6E	56.95 (16)	C7H—C5H—C6H—N1H	115.33 (13)
C9E—C5E—C6E—O6E	−60.87 (16)	C6H—C5H—C7H—C8H	−61.17 (16)
C4E—C5E—C6E—N1E	−1.17 (17)	C9H—C5H—C7H—C8H	−178.97 (13)
C7E—C5E—C6E—N1E	−123.74 (13)	C4H—C5H—C7H—C8H	62.55 (16)
C9E—C5E—C6E—N1E	118.45 (13)	C6H—C5H—C9H—C10H	62.66 (15)
C6E—C5E—C7E—C8E	66.11 (15)	C4H—C5H—C9H—C10H	−61.55 (15)
C4E—C5E—C7E—C8E	−58.71 (16)	C7H—C5H—C9H—C10H	179.72 (12)
C9E—C5E—C7E—C8E	−176.83 (12)	Cl44—C44—Cl43—Cl46	94.3 (10)
C6E—C5E—C9E—C10E	−61.54 (16)	Cl42—C44—Cl43—Cl46	−20.6 (11)
C4E—C5E—C9E—C10E	61.42 (15)	Cl41—C44—Cl43—Cl46	104.7 (10)
C7E—C5E—C9E—C10E	−179.49 (13)	Cl45—C44—Cl43—Cl46	−30.0 (10)
C6F—N1F—C2F—O2F	−178.71 (13)	Cl44—C44—Cl46—Cl43	−92.4 (10)
C6F—N1F—C2F—N3F	1.5 (2)	Cl42—C44—Cl46—Cl43	161.3 (10)
O2F—C2F—N3F—C4F	−179.93 (13)	Cl41—C44—Cl46—Cl43	−81.3 (10)
N1F—C2F—N3F—C4F	−0.2 (2)	Cl45—C44—Cl46—Cl43	152.1 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O6E	0.787 (19)	1.92 (2)	2.7044 (14)	175.3 (19)
C7A—H7A1···O4F	0.99	2.60	3.3209 (19)	130
N2A—H11A···O4Hⁱ	0.91 (1)	2.00 (1)	2.8366 (14)	153 (2)
N2A—H12A···N3Fⁱⁱ	0.91 (1)	2.06 (1)	2.8931 (15)	153 (2)
N2A—H13A···O4F	0.91 (1)	1.83 (1)	2.7269 (15)	170 (2)
O1B—H1B···O2F	0.804 (18)	1.797 (18)	2.5968 (14)	172.5 (18)
C6B—H6B···N3Hⁱⁱⁱ	0.95	2.69	3.5178 (18)	146
C8B—H8B1···O2H^iv	0.99	2.52	3.0956 (17)	117
N2B—H11B···O1A^v	0.91 (1)	1.97 (1)	2.8423 (15)	161 (2)
N2B—H12B···N3H^iv	0.92 (1)	1.99 (1)	2.8922 (16)	167 (2)
N2B—H13B···O1B^vi	0.91 (1)	2.37 (2)	2.9695 (15)	124 (1)
N2B—H13B···O6G^vi	0.91 (1)	2.11 (1)	2.7936 (15)	132 (1)
O1C—H1C···O2G	0.802 (18)	1.817 (18)	2.6173 (13)	175.5 (18)
C6C—H6C···N3E^vii	0.95	2.66	3.4764 (18)	145
N2C—H11C···O1D^viii	0.91 (1)	1.99 (1)	2.8595 (16)	160 (2)
N2C—H12C···O1C^ix	0.91 (1)	2.43 (2)	2.9621 (15)	118 (1)
N2C—H12C···O6F^ix	0.91 (1)	2.06 (1)	2.7785 (15)	135 (1)
N2C—H13C···N3Eⁱⁱ	0.91 (1)	1.97 (1)	2.8629 (16)	165 (2)
O1D—H1D···O6H	0.812 (19)	1.88 (2)	2.6940 (14)	177.5 (19)
N2D—H11D···O4G	0.90 (1)	1.82 (1)	2.7220 (15)	174 (2)
N2D—H12D···N3G^iv	0.90 (1)	2.03 (1)	2.8558 (15)	153 (2)
N2D—H13D···O4E^x	0.91 (1)	1.98 (1)	2.7976 (15)	149 (2)
N1E—H1E···O2H^xi	0.88 (1)	1.93 (1)	2.8053 (15)	173 (2)
N1F—H1F···O2G	0.88 (1)	1.88 (1)	2.7593 (14)	176 (2)
N1G—H1G···O2F	0.89 (1)	1.89 (1)	2.7703 (14)	175 (2)
N1H—H1H···O2E^xii	0.88 (1)	1.95 (1)	2.8122 (15)	170 (2)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y, −z; (vi) −x+3/2, y−1/2, −z+1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) −x+1, −y+2, −z+1; (ix) −x+1/2, y+1/2, −z+1/2; (x) −x+3/2, y+1/2, −z+1/2; (xi) x, y−1, z−1; (xii) x, y+1, z+1.

2-(4-Hydroxyphenyl)ethanaminium 5,5-diethyl-2,4,6-trioxotetrahydro-2H-pyrimidin-1-ide' (II) top