(S)-(+)-cis-4′-Benzyl­oxypraziquantel

Cedillo-Cruz, A.; Aguilar, M.I.; Jung-Cook, H.

doi:10.1107/S1600536813031735

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1835-o1836

doi:10.1107/S1600536813031735

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(S)-(+)-cis-4′-Benzyloxypraziquantel

Alberto Cedillo-Cruz,^a ^* María Isabel Aguilar ^a and Helgi Jung-Cook ^a

^aDepartamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, 04510 México, DF, Mexico
^*Correspondence e-mail: albertocedillo_cruz@hotmail.com

(Received 31 October 2013; accepted 20 November 2013; online 30 November 2013)

The asymmetric unit of the title compound, C₂₆H₃₀N₂O₃ {systematic name (S)-(+)-2-[cis-4-(benzyloxy)cyclohexanecarbonyl]-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one}, consists of two independent molecules in which the O= C_amide group is syn to the N—C(C=O_lactam) moiety, making dihedral angles of 2.0 (8) and 3.7 (8)°. The conformation of the 1,4-disubstituted cyclohexane ring is cis in each independent molecule, with the carbonyl group occupying an equatorial position and the benzyloxy group an axial position. In one molecule, two C and one O atom of the benzyloxy group are disordered over two sets of sites, with a refined occupancy ratio of 0.772 (8):0.228 (8). In the crystal, molecules are linked by C—H⋯O interactions, forming ribbons parallel to the b-axis direction.

CCDC reference: 972981

Related literature

For pyrazinoisoquinolone derivatives with anthelmintic activity, see: Staudt et al. (1992 ); Jung et al. (2008 ); Thétiot-Laurent et al. (2013 ); Duan et al. (2012 ); Patra et al. (2013 ); Wang et al. (2013 ); Meier & Blaschke (2001 ).

Experimental

Crystal data

C₂₆H₃₀N₂O₃
M_r = 418.52
Monoclinic, P 2₁
a = 15.007 (2) Å
b = 10.3322 (8) Å
c = 16.019 (2) Å
β = 117.399 (13)°
V = 2205.2 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 130 K
0.59 × 0.31 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011 ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.937, T_max = 0.979
8420 measured reflections
5852 independent reflections
3845 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.137
S = 1.03
5852 reflections
558 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack parameter determined using 868 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.4 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O2ⁱ	0.99	2.45	3.332 (7)	149
C20A—H20C⋯O2Aⁱⁱ	0.99	2.60	3.567 (10)	165
C20B—H20F⋯O2Aⁱⁱ	0.99	2.26	3.19 (3)	156
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 972981

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813031735/rz5093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031735/rz5093Isup2.hkl

checkCIF report

Comment top

The importance of pyrazinoisoquinolone derivatives as anthelmintics is well established (Jung et al., 2008; Thétiot-Laurent et al., 2013). Extensive number of derivatives has been synthesized, nevertheless at the date there are none with an activity comparable to that of praziquantel (Duan et al., 2012; Patra et al., 2013; Wang et al., 2013). Such compounds usually have an asymmetric carbon atom and only one of the enantiomers presents anthelmintic activity, often the enantiomer with (R)-(-)-configuration (Staudt et al., 1992). Herein, we report the synthesis and crystal structure of the title compound, (S)-(+)-cis-4 -benzyloxypraziquantel (Fig. 1), as a key intermediate for the synthesis of (S)-(+)-cis-4 -hydroxypraziquantel, one of the main metabolites of praziquantel (Meier & Blaschke, 2001).

The most stable conformation for (S)-(+)-cis-4'-benzyloxypraziquantel is observed where the O═ C_amide group is syn to the N–C(C═O_lactam) moiety with a dihedral angle of 2.0 (8) and 3.7 (8)° for the two independent molecules per asymmetric unit. Furthermore, the conformation of the 1,4-disubstituted cyclohexane is cis, where the carbonyl moiety occupies an equatorial position and the benzyloxy moiety occupies an axial position. In the crystal (Fig. 2), molecules are linked by intermolecular C—H···O hydrogen interactions (Table 1) to form ribbons parallel to the b axis.

Related literature top

For derivatives with anthelmintic activity, see: Staudt et al. (1992); Jung et al. (2008); Thétiot-Laurent et al. (2013); Duan et al. (2012); Patra et al. (2013); Wang et al. (2013); Meier & Blaschke (2001).

Experimental top

To a solution of (S)-(+)-praziquanamine (505.5 mg, 2.50 mmol) and 4-methylmorpholine (1.4 ml, 12.73) in dichloromethane (35 ml) under nitrogen atmosphere, a solution of cis-4-(benzyloxy)cyclohexanecarbonyl chloride (586 mg, 2.50 mmol) in dichloromethane (15 ml) was added dropwise at 0°C. After stirring at room temperature for 2 h, dichloromethane (50 ml) was added. The organic layer was successively washed with 1 M HCl (3 · 50 ml), saturated solution of NaHCO₃ (3 · 50 ml), water (3 · 50 ml) and dried over Na₂SO₄, filtered and concentrated. The residue was purified by column chromatography (SiO₂, ethyl acetate 100%). A white powder was obtained (935.7 mg, 89% yield). m.p. 405–408 K. Single-crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in methanol at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity. Only the major component of the disordered atoms is shown.
	Fig. 2. Intermolecular C—H···O interactions (dotted lines) forming ribbons parallel to the b axis in the title compound. Only the major components of the disordered atoms are shown.

(S)-(+)-2-[cis-4-(Benzyloxy)cyclohexanecarbonyl]-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one top

Crystal data top

C₂₆H₃₀N₂O₃	D_x = 1.261 Mg m⁻³
M_r = 418.52	Melting point = 405–408 K
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 15.007 (2) Å	Cell parameters from 1613 reflections
b = 10.3322 (8) Å	θ = 3.3–73.3°
c = 16.019 (2) Å	µ = 0.66 mm⁻¹
β = 117.399 (13)°	T = 130 K
V = 2205.2 (5) Å³	Needle, colourless
Z = 4	0.59 × 0.31 × 0.13 mm
F(000) = 896

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	5852 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 10.4685 pixels mm^-1	θ_max = 68.3°, θ_min = 5.5°
ω scans	h = −17→18
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]	k = −12→7
T_min = 0.937, T_max = 0.979	l = −19→18
8420 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0462P)² + 0.6847P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.137	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.25 e Å⁻³
5852 reflections	Δρ_min = −0.23 e Å⁻³
558 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.00115 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack parameter determined using 868 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.382 (265)

Crystal data top

C₂₆H₃₀N₂O₃	V = 2205.2 (5) Å³
M_r = 418.52	Z = 4
Monoclinic, P2₁	Cu Kα radiation
a = 15.007 (2) Å	µ = 0.66 mm⁻¹
b = 10.3322 (8) Å	T = 130 K
c = 16.019 (2) Å	0.59 × 0.31 × 0.13 mm
β = 117.399 (13)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	5852 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)]	3845 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.979	R_int = 0.057
8420 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.137	Δρ_max = 0.25 e Å⁻³
S = 1.03	Δρ_min = −0.23 e Å⁻³
5852 reflections	Absolute structure: Flack parameter determined using 868 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
558 parameters	Absolute structure parameter: 0.382 (265)
4 restraints

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.6375 (3)	0.2009 (4)	0.7391 (3)	0.0452 (10)
O2	0.2778 (3)	0.1973 (4)	0.5624 (3)	0.0489 (11)
N1	0.5909 (3)	0.4128 (4)	0.7198 (3)	0.0346 (11)
N2	0.3976 (3)	0.3440 (4)	0.5860 (3)	0.0350 (11)
C12	0.5135 (3)	0.5133 (5)	0.6799 (3)	0.0289 (12)
H12	0.4792	0.5224	0.7203	0.035*
C13	0.3000 (4)	0.3110 (5)	0.5562 (4)	0.0341 (13)
C16	0.0377 (4)	0.4631 (6)	0.4195 (4)	0.0423 (15)
H16C	−0.0294	0.4226	0.3863	0.051*
H16D	0.0492	0.5139	0.3729	0.051*
C2	0.4924 (4)	0.7477 (5)	0.6361 (3)	0.0331 (13)
H2	0.4226	0.7356	0.6154	0.040*
C19	0.2203 (4)	0.4976 (5)	0.5981 (4)	0.0351 (13)
H19A	0.2028	0.4424	0.6389	0.042*
H19B	0.2880	0.5341	0.6369	0.042*
C9	0.5738 (4)	0.2851 (6)	0.6990 (4)	0.0349 (13)
O3	0.0086 (3)	0.4888 (4)	0.5570 (3)	0.0477 (11)
C1	0.5582 (4)	0.6432 (5)	0.6747 (3)	0.0286 (12)
C11	0.4367 (4)	0.4709 (5)	0.5816 (4)	0.0330 (12)
H11A	0.3811	0.5343	0.5554	0.040*
H11B	0.4687	0.4678	0.5396	0.040*
C10	0.4747 (4)	0.2445 (5)	0.6220 (4)	0.0386 (14)
H10A	0.4852	0.2116	0.5692	0.046*
H10B	0.4494	0.1715	0.6452	0.046*
C14	0.2207 (4)	0.4154 (5)	0.5181 (4)	0.0350 (13)
H14	0.2362	0.4734	0.4765	0.042*
C7	0.7334 (4)	0.5547 (6)	0.7575 (4)	0.0434 (15)
H7A	0.7946	0.5911	0.8099	0.052*
H7B	0.7533	0.5123	0.7132	0.052*
C15	0.1172 (4)	0.3573 (6)	0.4602 (4)	0.0396 (14)
H15C	0.1008	0.2991	0.5003	0.048*
H15D	0.1172	0.3051	0.4083	0.048*
C17	0.0396 (4)	0.5545 (6)	0.4957 (4)	0.0409 (14)
H17	−0.0072	0.6283	0.4648	0.049*
C6	0.6612 (4)	0.6616 (5)	0.7082 (3)	0.0324 (13)
C22	−0.2257 (4)	0.3782 (7)	0.5544 (4)	0.0466 (16)
H22	−0.2742	0.4268	0.5034	0.056*
C18	0.1439 (4)	0.6076 (6)	0.5572 (4)	0.0421 (15)
H18A	0.1432	0.6589	0.6091	0.051*
H18B	0.1638	0.6656	0.5195	0.051*
C8	0.6880 (4)	0.4558 (6)	0.7955 (4)	0.0444 (16)
H8A	0.7338	0.3809	0.8208	0.053*
H8B	0.6781	0.4941	0.8473	0.053*
C5	0.6944 (4)	0.7833 (6)	0.6972 (4)	0.0432 (15)
H5	0.7638	0.7960	0.7165	0.052*
C21	−0.1238 (4)	0.3933 (6)	0.5797 (4)	0.0406 (14)
C3	0.5275 (4)	0.8674 (5)	0.6280 (3)	0.0372 (14)
H3	0.4820	0.9372	0.6010	0.045*
C23	−0.2566 (5)	0.2938 (7)	0.6023 (4)	0.0524 (18)
H23	−0.3262	0.2839	0.5838	0.063*
C20	−0.0961 (4)	0.4757 (7)	0.5179 (5)	0.0506 (16)
H20A	−0.1224	0.4356	0.4549	0.061*
H20B	−0.1271	0.5623	0.5104	0.061*
C26	−0.0555 (4)	0.3261 (6)	0.6553 (4)	0.0446 (15)
H26	0.0142	0.3372	0.6747	0.054*
C25	−0.0867 (4)	0.2407 (7)	0.7045 (4)	0.0514 (17)
H25	−0.0380	0.1946	0.7569	0.062*
C4	0.6288 (4)	0.8862 (6)	0.6590 (4)	0.0433 (15)
H4	0.6535	0.9691	0.6542	0.052*
C24	−0.1862 (4)	0.2229 (7)	0.6780 (4)	0.0547 (18)
H24	−0.2072	0.1632	0.7106	0.066*
C15A	0.0948 (4)	0.3602 (6)	−0.0635 (4)	0.0425 (14)
H15A	0.0977	0.3212	−0.1187	0.051*
H15B	0.0790	0.2905	−0.0300	0.051*
C16A	0.0117 (4)	0.4614 (6)	−0.0971 (4)	0.0434 (15)
H16A	0.0228	0.5251	−0.1375	0.052*
H16B	−0.0537	0.4187	−0.1353	0.052*
N1A	0.5699 (3)	0.4053 (4)	0.2033 (3)	0.0333 (10)
O1A	0.6124 (3)	0.1921 (4)	0.2158 (3)	0.0442 (10)
N2A	0.3746 (3)	0.3446 (4)	0.0686 (3)	0.0354 (11)
C13A	0.2762 (4)	0.3121 (6)	0.0364 (4)	0.0389 (14)
C1A	0.5421 (4)	0.6375 (5)	0.1644 (3)	0.0313 (12)
O2A	0.2541 (3)	0.1984 (4)	0.0393 (3)	0.0564 (12)
C10A	0.4491 (4)	0.2433 (5)	0.0997 (4)	0.0392 (14)
H10C	0.4583	0.2142	0.0453	0.047*
H10D	0.4228	0.1688	0.1205	0.047*
C11A	0.4143 (4)	0.4725 (5)	0.0676 (4)	0.0350 (13)
H11C	0.3594	0.5369	0.0457	0.042*
H11D	0.4437	0.4735	0.0235	0.042*
C9A	0.5500 (4)	0.2787 (5)	0.1779 (4)	0.0357 (13)
C12A	0.4943 (4)	0.5080 (5)	0.1658 (4)	0.0316 (12)
H12A	0.4615	0.5162	0.2075	0.038*
C14A	0.1972 (4)	0.4180 (6)	0.0019 (4)	0.0387 (13)
H14A	0.2153	0.4826	−0.0343	0.046*
C19A	0.1934 (4)	0.4876 (6)	0.0849 (4)	0.0428 (14)
H19C	0.1809	0.4239	0.1244	0.051*
H19D	0.2587	0.5300	0.1241	0.051*
C6A	0.6451 (4)	0.6533 (6)	0.1976 (4)	0.0359 (13)
C2A	0.4790 (4)	0.7449 (5)	0.1282 (3)	0.0356 (13)
H2A	0.4087	0.7350	0.1058	0.043*
C5A	0.6826 (4)	0.7736 (6)	0.1926 (4)	0.0435 (15)
H5A	0.7528	0.7837	0.2143	0.052*
C4A	0.6206 (5)	0.8790 (6)	0.1570 (4)	0.0500 (17)
H4A	0.6478	0.9610	0.1544	0.060*
C8A	0.6671 (4)	0.4424 (6)	0.2795 (4)	0.0460 (16)
H8D	0.7109	0.3653	0.3025	0.055*
H8C	0.6581	0.4783	0.3325	0.055*
C7A	0.7157 (4)	0.5424 (6)	0.2450 (4)	0.0443 (15)
H7C	0.7772	0.5757	0.2988	0.053*
H7D	0.7355	0.5017	0.2001	0.053*
C18A	0.1100 (5)	0.5890 (6)	0.0485 (4)	0.0485 (16)
H18C	0.1071	0.6313	0.1026	0.058*
H18D	0.1261	0.6563	0.0135	0.058*
C21A	−0.1020 (7)	0.3739 (16)	0.1231 (8)	0.0531 (12)	0.772 (8)
C17A	0.0086 (5)	0.5313 (6)	−0.0152 (5)	0.0531 (12)
H17A	−0.0413	0.6033	−0.0408	0.064*
C3A	0.5177 (4)	0.8653 (6)	0.1249 (3)	0.0398 (14)
H3A	0.4744	0.9379	0.1008	0.048*
C26A	−0.0429 (5)	0.2988 (7)	0.1947 (5)	0.0605 (19)
H26A	0.0269	0.3168	0.2272	0.073*
C23A	−0.2459 (5)	0.2612 (8)	0.1121 (5)	0.064 (2)
H23A	−0.3163	0.2473	0.0829	0.077*
C24A	−0.1851 (5)	0.1881 (8)	0.1876 (5)	0.0590 (19)
H24A	−0.2136	0.1248	0.2113	0.071*
C25A	−0.0821 (5)	0.2051 (7)	0.2303 (5)	0.0610 (19)
H25A	−0.0394	0.1537	0.2827	0.073*
C22A	−0.2069 (5)	0.3544 (8)	0.0777 (5)	0.064 (2)
H22A	−0.2511	0.4107	0.0296	0.076*
O3A	−0.0272 (4)	0.4294 (5)	0.0256 (4)	0.0387 (13)	0.772 (8)
C20A	−0.0532 (7)	0.4814 (9)	0.0929 (7)	0.0531 (12)	0.772 (8)
H20C	−0.1006	0.5544	0.0654	0.064*	0.772 (8)
H20D	0.0075	0.5139	0.1479	0.064*	0.772 (8)
O3B	0.0059 (15)	0.481 (2)	0.0661 (14)	0.0387 (13)	0.228 (8)
C20B	−0.106 (2)	0.457 (3)	0.0344 (19)	0.0531 (12)	0.228 (8)
H20E	−0.1384	0.4129	−0.0276	0.064*	0.228 (8)
H20F	−0.1422	0.5381	0.0309	0.064*	0.228 (8)
C21B	−0.1030 (16)	0.369 (5)	0.112 (3)	0.0531 (12)	0.228 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.049 (2)	0.033 (2)	0.063 (3)	0.014 (2)	0.034 (2)	0.006 (2)
O2	0.043 (2)	0.028 (2)	0.069 (3)	−0.0077 (19)	0.020 (2)	0.003 (2)
N1	0.041 (2)	0.028 (3)	0.032 (2)	0.007 (2)	0.0143 (19)	−0.001 (2)
N2	0.036 (2)	0.025 (3)	0.046 (3)	−0.002 (2)	0.021 (2)	0.003 (2)
C12	0.032 (3)	0.027 (3)	0.032 (3)	0.008 (2)	0.018 (2)	0.006 (2)
C13	0.038 (3)	0.032 (3)	0.034 (3)	−0.004 (3)	0.018 (2)	−0.003 (3)
C16	0.038 (3)	0.047 (4)	0.037 (3)	−0.001 (3)	0.014 (2)	0.003 (3)
C2	0.036 (3)	0.031 (3)	0.033 (3)	−0.002 (3)	0.016 (2)	−0.001 (3)
C19	0.035 (3)	0.032 (3)	0.037 (3)	−0.001 (3)	0.016 (2)	0.000 (3)
C9	0.041 (3)	0.032 (3)	0.045 (3)	0.008 (3)	0.030 (3)	0.009 (3)
O3	0.0348 (19)	0.057 (3)	0.049 (2)	0.006 (2)	0.0168 (18)	0.010 (2)
C1	0.038 (3)	0.024 (3)	0.026 (3)	0.005 (2)	0.018 (2)	0.003 (2)
C11	0.033 (3)	0.030 (3)	0.039 (3)	0.004 (2)	0.018 (2)	0.004 (3)
C10	0.048 (3)	0.023 (3)	0.052 (4)	0.005 (3)	0.030 (3)	0.001 (3)
C14	0.035 (3)	0.031 (3)	0.040 (3)	−0.005 (3)	0.018 (2)	0.000 (3)
C7	0.036 (3)	0.041 (4)	0.044 (3)	0.000 (3)	0.011 (3)	−0.008 (3)
C15	0.040 (3)	0.035 (4)	0.041 (3)	−0.003 (3)	0.016 (3)	−0.001 (3)
C17	0.042 (3)	0.039 (4)	0.044 (3)	0.009 (3)	0.022 (3)	0.014 (3)
C6	0.035 (3)	0.032 (3)	0.029 (3)	−0.002 (3)	0.013 (2)	−0.007 (2)
C22	0.036 (3)	0.065 (5)	0.044 (3)	0.007 (3)	0.022 (3)	−0.006 (3)
C18	0.048 (3)	0.035 (4)	0.042 (3)	−0.002 (3)	0.020 (3)	−0.006 (3)
C8	0.039 (3)	0.045 (4)	0.035 (3)	0.013 (3)	0.005 (2)	0.001 (3)
C5	0.041 (3)	0.043 (4)	0.048 (3)	−0.011 (3)	0.022 (3)	−0.009 (3)
C21	0.034 (3)	0.043 (4)	0.045 (3)	0.002 (3)	0.018 (3)	−0.006 (3)
C3	0.047 (3)	0.029 (3)	0.032 (3)	−0.004 (3)	0.016 (2)	−0.001 (3)
C23	0.047 (4)	0.077 (5)	0.041 (3)	−0.012 (3)	0.027 (3)	−0.011 (4)
C20	0.036 (3)	0.048 (4)	0.065 (4)	0.004 (3)	0.020 (3)	0.012 (4)
C26	0.038 (3)	0.043 (4)	0.047 (3)	−0.005 (3)	0.015 (3)	−0.004 (3)
C25	0.054 (4)	0.049 (4)	0.041 (3)	−0.004 (3)	0.013 (3)	−0.008 (3)
C4	0.052 (4)	0.037 (4)	0.041 (3)	−0.013 (3)	0.022 (3)	−0.008 (3)
C24	0.056 (4)	0.067 (5)	0.051 (4)	−0.017 (4)	0.033 (3)	−0.012 (4)
C15A	0.037 (3)	0.040 (4)	0.047 (3)	−0.006 (3)	0.017 (3)	−0.002 (3)
C16A	0.041 (3)	0.040 (4)	0.046 (3)	0.000 (3)	0.018 (3)	0.012 (3)
N1A	0.039 (2)	0.024 (3)	0.038 (2)	0.004 (2)	0.019 (2)	0.005 (2)
O1A	0.048 (2)	0.028 (2)	0.065 (3)	0.008 (2)	0.032 (2)	0.008 (2)
N2A	0.041 (3)	0.021 (2)	0.047 (3)	0.002 (2)	0.022 (2)	0.003 (2)
C13A	0.042 (3)	0.033 (4)	0.038 (3)	−0.008 (3)	0.016 (3)	−0.002 (3)
C1A	0.038 (3)	0.033 (3)	0.024 (3)	−0.003 (3)	0.016 (2)	−0.001 (2)
O2A	0.047 (2)	0.031 (3)	0.085 (3)	−0.007 (2)	0.025 (2)	0.007 (2)
C10A	0.050 (3)	0.021 (3)	0.050 (3)	0.000 (3)	0.025 (3)	−0.001 (3)
C11A	0.044 (3)	0.027 (3)	0.036 (3)	−0.004 (3)	0.020 (3)	0.000 (3)
C9A	0.047 (3)	0.028 (3)	0.044 (3)	0.003 (3)	0.031 (3)	0.009 (3)
C12A	0.043 (3)	0.023 (3)	0.036 (3)	0.003 (3)	0.025 (2)	0.004 (2)
C14A	0.042 (3)	0.030 (3)	0.042 (3)	−0.003 (3)	0.017 (3)	0.001 (3)
C19A	0.050 (3)	0.038 (4)	0.038 (3)	0.000 (3)	0.019 (3)	0.000 (3)
C6A	0.045 (3)	0.032 (3)	0.036 (3)	−0.006 (3)	0.023 (3)	−0.004 (3)
C2A	0.048 (3)	0.030 (3)	0.032 (3)	−0.001 (3)	0.021 (3)	0.000 (3)
C5A	0.048 (3)	0.047 (4)	0.034 (3)	−0.016 (3)	0.018 (3)	−0.005 (3)
C4A	0.070 (4)	0.040 (4)	0.039 (3)	−0.024 (4)	0.024 (3)	−0.009 (3)
C8A	0.047 (3)	0.041 (4)	0.044 (3)	0.006 (3)	0.016 (3)	0.002 (3)
C7A	0.038 (3)	0.043 (4)	0.052 (4)	−0.004 (3)	0.021 (3)	−0.007 (3)
C18A	0.072 (4)	0.035 (4)	0.039 (3)	0.009 (3)	0.026 (3)	0.003 (3)
C21A	0.063 (3)	0.045 (3)	0.066 (3)	0.005 (2)	0.042 (2)	−0.002 (2)
C17A	0.063 (3)	0.045 (3)	0.066 (3)	0.005 (2)	0.042 (2)	−0.002 (2)
C3A	0.063 (4)	0.025 (3)	0.034 (3)	−0.004 (3)	0.025 (3)	−0.002 (3)
C26A	0.051 (4)	0.050 (5)	0.080 (5)	−0.010 (3)	0.029 (4)	−0.021 (4)
C23A	0.049 (4)	0.099 (6)	0.048 (4)	−0.012 (4)	0.025 (3)	−0.022 (4)
C24A	0.062 (4)	0.072 (5)	0.055 (4)	−0.027 (4)	0.037 (4)	−0.021 (4)
C25A	0.063 (4)	0.064 (5)	0.052 (4)	0.004 (4)	0.022 (3)	−0.008 (4)
C22A	0.066 (4)	0.075 (6)	0.065 (4)	0.020 (4)	0.043 (4)	0.006 (4)
O3A	0.051 (3)	0.030 (3)	0.040 (3)	−0.004 (3)	0.025 (3)	−0.009 (2)
C20A	0.063 (3)	0.045 (3)	0.066 (3)	0.005 (2)	0.042 (2)	−0.002 (2)
O3B	0.051 (3)	0.030 (3)	0.040 (3)	−0.004 (3)	0.025 (3)	−0.009 (2)
C20B	0.063 (3)	0.045 (3)	0.066 (3)	0.005 (2)	0.042 (2)	−0.002 (2)
C21B	0.063 (3)	0.045 (3)	0.066 (3)	0.005 (2)	0.042 (2)	−0.002 (2)

Geometric parameters (Å, º) top

O1—C9	1.232 (6)	C16A—C17A	1.517 (8)
O2—C13	1.238 (6)	C16A—H16A	0.9900
N1—C9	1.356 (7)	C16A—H16B	0.9900
N1—C12	1.467 (6)	N1A—C9A	1.362 (7)
N1—C8	1.471 (6)	N1A—C8A	1.458 (7)
N2—C13	1.358 (6)	N1A—C12A	1.465 (6)
N2—C11	1.452 (7)	O1A—C9A	1.234 (6)
N2—C10	1.455 (6)	N2A—C13A	1.364 (7)
C12—C1	1.519 (7)	N2A—C10A	1.443 (7)
C12—C11	1.526 (7)	N2A—C11A	1.452 (6)
C12—H12	1.0000	C13A—O2A	1.227 (6)
C13—C14	1.512 (7)	C13A—C14A	1.518 (8)
C16—C15	1.526 (8)	C1A—C6A	1.394 (7)
C16—C17	1.533 (8)	C1A—C2A	1.400 (7)
C16—H16C	0.9900	C1A—C12A	1.523 (7)
C16—H16D	0.9900	C10A—C9A	1.499 (7)
C2—C3	1.374 (7)	C10A—H10C	0.9900
C2—C1	1.401 (7)	C10A—H10D	0.9900
C2—H2	0.9500	C11A—C12A	1.521 (7)
C19—C18	1.531 (7)	C11A—H11C	0.9900
C19—C14	1.540 (7)	C11A—H11D	0.9900
C19—H19A	0.9900	C12A—H12A	1.0000
C19—H19B	0.9900	C14A—C19A	1.535 (8)
C9—C10	1.489 (7)	C14A—H14A	1.0000
O3—C20	1.405 (6)	C19A—C18A	1.527 (8)
O3—C17	1.436 (6)	C19A—H19C	0.9900
C1—C6	1.396 (7)	C19A—H19D	0.9900
C11—H11A	0.9900	C6A—C5A	1.382 (8)
C11—H11B	0.9900	C6A—C7A	1.507 (8)
C10—H10A	0.9900	C2A—C3A	1.385 (7)
C10—H10B	0.9900	C2A—H2A	0.9500
C14—C15	1.519 (7)	C5A—C4A	1.375 (9)
C14—H14	1.0000	C5A—H5A	0.9500
C7—C6	1.494 (7)	C4A—C3A	1.392 (8)
C7—C8	1.504 (8)	C4A—H4A	0.9500
C7—H7A	0.9900	C8A—C7A	1.509 (8)
C7—H7B	0.9900	C8A—H8D	0.9900
C15—H15C	0.9900	C8A—H8C	0.9900
C15—H15D	0.9900	C7A—H7C	0.9900
C17—C18	1.517 (8)	C7A—H7D	0.9900
C17—H17	1.0000	C18A—C17A	1.511 (9)
C6—C5	1.392 (8)	C18A—H18C	0.9900
C22—C23	1.376 (8)	C18A—H18D	0.9900
C22—C21	1.398 (7)	C21A—C26A	1.330 (12)
C22—H22	0.9500	C21A—C22A	1.412 (12)
C18—H18A	0.9900	C21A—C20A	1.526 (14)
C18—H18B	0.9900	C17A—O3B	1.418 (19)
C8—H8A	0.9900	C17A—O3A	1.466 (8)
C8—H8B	0.9900	C17A—H17A	1.0000
C5—C4	1.386 (8)	C3A—H3A	0.9500
C5—H5	0.9500	C26A—C25A	1.384 (9)
C21—C26	1.363 (8)	C26A—C21B	1.410 (12)
C21—C20	1.502 (8)	C26A—H26A	0.9500
C3—C4	1.379 (7)	C23A—C24A	1.360 (10)
C3—H3	0.9500	C23A—C22A	1.367 (10)
C23—C24	1.394 (9)	C23A—H23A	0.9500
C23—H23	0.9500	C24A—C25A	1.383 (8)
C20—H20A	0.9900	C24A—H24A	0.9500
C20—H20B	0.9900	C25A—H25A	0.9500
C26—C25	1.400 (8)	C22A—C21B	1.40 (2)
C26—H26	0.9500	C22A—H22A	0.9500
C25—C24	1.364 (8)	O3A—C20A	1.411 (10)
C25—H25	0.9500	C20A—H20C	0.9900
C4—H4	0.9500	C20A—H20D	0.9900
C24—H24	0.9500	O3B—C20B	1.54 (3)
C15A—C16A	1.523 (7)	C20B—C21B	1.523 (12)
C15A—C14A	1.528 (7)	C20B—H20E	0.9900
C15A—H15A	0.9900	C20B—H20F	0.9900
C15A—H15B	0.9900

C9—N1—C12	124.0 (4)	C17A—C16A—H16A	109.3
C9—N1—C8	120.1 (4)	C15A—C16A—H16A	109.3
C12—N1—C8	115.5 (4)	C17A—C16A—H16B	109.3
C13—N2—C11	127.2 (4)	C15A—C16A—H16B	109.3
C13—N2—C10	119.6 (5)	H16A—C16A—H16B	108.0
C11—N2—C10	113.1 (4)	C9A—N1A—C8A	120.0 (5)
N1—C12—C1	111.6 (4)	C9A—N1A—C12A	123.4 (4)
N1—C12—C11	108.5 (4)	C8A—N1A—C12A	116.2 (4)
C1—C12—C11	109.9 (4)	C13A—N2A—C10A	118.9 (5)
N1—C12—H12	108.9	C13A—N2A—C11A	126.8 (5)
C1—C12—H12	108.9	C10A—N2A—C11A	114.0 (4)
C11—C12—H12	108.9	O2A—C13A—N2A	119.1 (5)
O2—C13—N2	119.8 (5)	O2A—C13A—C14A	121.6 (5)
O2—C13—C14	121.3 (5)	N2A—C13A—C14A	119.2 (5)
N2—C13—C14	118.9 (5)	C6A—C1A—C2A	119.0 (5)
C15—C16—C17	112.1 (4)	C6A—C1A—C12A	123.0 (5)
C15—C16—H16C	109.2	C2A—C1A—C12A	118.0 (4)
C17—C16—H16C	109.2	N2A—C10A—C9A	115.8 (5)
C15—C16—H16D	109.2	N2A—C10A—H10C	108.3
C17—C16—H16D	109.2	C9A—C10A—H10C	108.3
H16C—C16—H16D	107.9	N2A—C10A—H10D	108.3
C3—C2—C1	120.8 (5)	C9A—C10A—H10D	108.3
C3—C2—H2	119.6	H10C—C10A—H10D	107.4
C1—C2—H2	119.6	N2A—C11A—C12A	109.9 (4)
C18—C19—C14	110.0 (4)	N2A—C11A—H11C	109.7
C18—C19—H19A	109.7	C12A—C11A—H11C	109.7
C14—C19—H19A	109.7	N2A—C11A—H11D	109.7
C18—C19—H19B	109.7	C12A—C11A—H11D	109.7
C14—C19—H19B	109.7	H11C—C11A—H11D	108.2
H19A—C19—H19B	108.2	O1A—C9A—N1A	122.5 (5)
O1—C9—N1	123.0 (5)	O1A—C9A—C10A	118.7 (5)
O1—C9—C10	118.2 (5)	N1A—C9A—C10A	118.9 (5)
N1—C9—C10	118.8 (5)	N1A—C12A—C11A	110.1 (4)
C20—O3—C17	112.8 (4)	N1A—C12A—C1A	111.2 (4)
C6—C1—C2	119.7 (5)	C11A—C12A—C1A	110.4 (4)
C6—C1—C12	122.5 (5)	N1A—C12A—H12A	108.4
C2—C1—C12	117.7 (4)	C11A—C12A—H12A	108.4
N2—C11—C12	109.8 (4)	C1A—C12A—H12A	108.4
N2—C11—H11A	109.7	C13A—C14A—C15A	109.8 (5)
C12—C11—H11A	109.7	C13A—C14A—C19A	110.9 (5)
N2—C11—H11B	109.7	C15A—C14A—C19A	110.5 (5)
C12—C11—H11B	109.7	C13A—C14A—H14A	108.5
H11A—C11—H11B	108.2	C15A—C14A—H14A	108.5
N2—C10—C9	116.0 (5)	C19A—C14A—H14A	108.5
N2—C10—H10A	108.3	C18A—C19A—C14A	110.0 (4)
C9—C10—H10A	108.3	C18A—C19A—H19C	109.7
N2—C10—H10B	108.3	C14A—C19A—H19C	109.7
C9—C10—H10B	108.3	C18A—C19A—H19D	109.7
H10A—C10—H10B	107.4	C14A—C19A—H19D	109.7
C13—C14—C15	111.0 (5)	H19C—C19A—H19D	108.2
C13—C14—C19	111.2 (4)	C5A—C6A—C1A	119.6 (6)
C15—C14—C19	109.4 (4)	C5A—C6A—C7A	120.1 (5)
C13—C14—H14	108.4	C1A—C6A—C7A	120.2 (5)
C15—C14—H14	108.4	C3A—C2A—C1A	120.8 (5)
C19—C14—H14	108.4	C3A—C2A—H2A	119.6
C6—C7—C8	111.3 (5)	C1A—C2A—H2A	119.6
C6—C7—H7A	109.4	C4A—C5A—C6A	121.3 (6)
C8—C7—H7A	109.4	C4A—C5A—H5A	119.3
C6—C7—H7B	109.4	C6A—C5A—H5A	119.3
C8—C7—H7B	109.4	C5A—C4A—C3A	119.8 (6)
H7A—C7—H7B	108.0	C5A—C4A—H4A	120.1
C14—C15—C16	110.8 (5)	C3A—C4A—H4A	120.1
C14—C15—H15C	109.5	N1A—C8A—C7A	109.8 (5)
C16—C15—H15C	109.5	N1A—C8A—H8D	109.7
C14—C15—H15D	109.5	C7A—C8A—H8D	109.7
C16—C15—H15D	109.5	N1A—C8A—H8C	109.7
H15C—C15—H15D	108.1	C7A—C8A—H8C	109.7
O3—C17—C18	106.8 (4)	H8D—C8A—H8C	108.2
O3—C17—C16	111.1 (5)	C6A—C7A—C8A	111.0 (5)
C18—C17—C16	112.1 (5)	C6A—C7A—H7C	109.4
O3—C17—H17	108.9	C8A—C7A—H7C	109.4
C18—C17—H17	108.9	C6A—C7A—H7D	109.4
C16—C17—H17	108.9	C8A—C7A—H7D	109.4
C5—C6—C1	118.1 (5)	H7C—C7A—H7D	108.0
C5—C6—C7	121.3 (5)	C17A—C18A—C19A	112.4 (5)
C1—C6—C7	120.5 (5)	C17A—C18A—H18C	109.1
C23—C22—C21	120.9 (6)	C19A—C18A—H18C	109.1
C23—C22—H22	119.6	C17A—C18A—H18D	109.1
C21—C22—H22	119.6	C19A—C18A—H18D	109.1
C17—C18—C19	110.8 (5)	H18C—C18A—H18D	107.9
C17—C18—H18A	109.5	C26A—C21A—C22A	120.2 (10)
C19—C18—H18A	109.5	C26A—C21A—C20A	118.1 (9)
C17—C18—H18B	109.5	C22A—C21A—C20A	121.7 (8)
C19—C18—H18B	109.5	O3B—C17A—C18A	88.3 (9)
H18A—C18—H18B	108.1	O3A—C17A—C18A	116.4 (5)
N1—C8—C7	109.4 (5)	O3B—C17A—C16A	130.2 (10)
N1—C8—H8A	109.8	O3A—C17A—C16A	101.9 (5)
C7—C8—H8A	109.8	C18A—C17A—C16A	110.4 (5)
N1—C8—H8B	109.8	O3B—C17A—H17A	108.4
C7—C8—H8B	109.8	C18A—C17A—H17A	108.4
H8A—C8—H8B	108.2	C16A—C17A—H17A	108.4
C4—C5—C6	121.7 (5)	C2A—C3A—C4A	119.4 (6)
C4—C5—H5	119.1	C2A—C3A—H3A	120.3
C6—C5—H5	119.1	C4A—C3A—H3A	120.3
C26—C21—C22	118.5 (6)	C21A—C26A—C25A	121.5 (8)
C26—C21—C20	123.4 (5)	C25A—C26A—C21B	122.4 (13)
C22—C21—C20	118.0 (5)	C25A—C26A—H26A	118.8
C2—C3—C4	120.0 (5)	C21B—C26A—H26A	118.8
C2—C3—H3	120.0	C24A—C23A—C22A	120.9 (6)
C4—C3—H3	120.0	C24A—C23A—H23A	119.6
C22—C23—C24	120.2 (6)	C22A—C23A—H23A	119.6
C22—C23—H23	119.9	C23A—C24A—C25A	120.5 (7)
C24—C23—H23	119.9	C23A—C24A—H24A	119.7
O3—C20—C21	110.6 (5)	C25A—C24A—H24A	119.7
O3—C20—H20A	109.5	C24A—C25A—C26A	118.4 (7)
C21—C20—H20A	109.5	C24A—C25A—H25A	120.8
O3—C20—H20B	109.5	C26A—C25A—H25A	120.8
C21—C20—H20B	109.5	C23A—C22A—C21B	121.4 (11)
H20A—C20—H20B	108.1	C23A—C22A—C21A	118.4 (7)
C21—C26—C25	120.7 (6)	C23A—C22A—H22A	119.3
C21—C26—H26	119.6	C21B—C22A—H22A	119.3
C25—C26—H26	119.6	C20A—O3A—C17A	110.8 (6)
C24—C25—C26	120.8 (6)	O3A—C20A—C21A	107.9 (9)
C24—C25—H25	119.6	O3A—C20A—H20C	110.1
C26—C25—H25	119.6	C21A—C20A—H20C	110.1
C3—C4—C5	119.5 (5)	O3A—C20A—H20D	110.1
C3—C4—H4	120.3	C21A—C20A—H20D	110.1
C5—C4—H4	120.3	H20C—C20A—H20D	108.4
C25—C24—C23	118.9 (6)	C17A—O3B—C20B	104.2 (15)
C25—C24—H24	120.6	O3B—C20B—C21B	102 (2)
C23—C24—H24	120.6	O3B—C20B—H20E	111.3
C16A—C15A—C14A	112.1 (5)	C21B—C20B—H20E	111.3
C16A—C15A—H15A	109.2	O3B—C20B—H20F	111.3
C14A—C15A—H15A	109.2	C21B—C20B—H20F	111.3
C16A—C15A—H15B	109.2	H20E—C20B—H20F	109.2
C14A—C15A—H15B	109.2	C22A—C21B—C26A	115.4 (16)
H15A—C15A—H15B	107.9	C22A—C21B—C20B	97.6 (14)
C17A—C16A—C15A	111.6 (5)	C26A—C21B—C20B	147 (2)

C9—N1—C12—C1	−151.7 (5)	C12A—N1A—C9A—C10A	7.3 (8)
C8—N1—C12—C1	36.5 (6)	N2A—C10A—C9A—O1A	170.6 (5)
C9—N1—C12—C11	−30.5 (7)	N2A—C10A—C9A—N1A	−10.6 (8)
C8—N1—C12—C11	157.7 (4)	C9A—N1A—C12A—C11A	−28.3 (7)
C11—N2—C13—O2	178.1 (5)	C8A—N1A—C12A—C11A	159.1 (5)
C10—N2—C13—O2	2.0 (8)	C9A—N1A—C12A—C1A	−151.0 (5)
C11—N2—C13—C14	−3.3 (8)	C8A—N1A—C12A—C1A	36.4 (6)
C10—N2—C13—C14	−179.4 (5)	N2A—C11A—C12A—N1A	52.6 (5)
C12—N1—C9—O1	−173.6 (5)	N2A—C11A—C12A—C1A	175.8 (4)
C8—N1—C9—O1	−2.2 (9)	C6A—C1A—C12A—N1A	−1.7 (7)
C12—N1—C9—C10	8.5 (8)	C2A—C1A—C12A—N1A	178.5 (4)
C8—N1—C9—C10	179.9 (5)	C6A—C1A—C12A—C11A	−124.2 (5)
C3—C2—C1—C6	2.1 (8)	C2A—C1A—C12A—C11A	56.0 (6)
C3—C2—C1—C12	−179.0 (5)	O2A—C13A—C14A—C15A	−24.5 (8)
N1—C12—C1—C6	−2.5 (7)	N2A—C13A—C14A—C15A	158.3 (5)
C11—C12—C1—C6	−122.8 (5)	O2A—C13A—C14A—C19A	97.9 (7)
N1—C12—C1—C2	178.7 (4)	N2A—C13A—C14A—C19A	−79.2 (7)
C11—C12—C1—C2	58.4 (6)	C16A—C15A—C14A—C13A	177.6 (5)
C13—N2—C11—C12	123.1 (5)	C16A—C15A—C14A—C19A	55.0 (7)
C10—N2—C11—C12	−60.6 (6)	C13A—C14A—C19A—C18A	−177.2 (5)
N1—C12—C11—N2	55.0 (5)	C15A—C14A—C19A—C18A	−55.2 (7)
C1—C12—C11—N2	177.3 (4)	C2A—C1A—C6A—C5A	−1.2 (8)
C13—N2—C10—C9	−146.1 (5)	C12A—C1A—C6A—C5A	179.0 (5)
C11—N2—C10—C9	37.3 (7)	C2A—C1A—C6A—C7A	174.3 (5)
O1—C9—C10—N2	171.7 (5)	C12A—C1A—C6A—C7A	−5.5 (8)
N1—C9—C10—N2	−10.4 (7)	C6A—C1A—C2A—C3A	0.3 (8)
O2—C13—C14—C15	−20.1 (7)	C12A—C1A—C2A—C3A	−179.9 (5)
N2—C13—C14—C15	161.4 (5)	C1A—C6A—C5A—C4A	1.1 (9)
O2—C13—C14—C19	101.9 (6)	C7A—C6A—C5A—C4A	−174.4 (5)
N2—C13—C14—C19	−76.7 (6)	C6A—C5A—C4A—C3A	−0.2 (9)
C18—C19—C14—C13	176.5 (4)	C9A—N1A—C8A—C7A	124.0 (5)
C18—C19—C14—C15	−60.6 (6)	C12A—N1A—C8A—C7A	−63.2 (6)
C13—C14—C15—C16	−178.4 (4)	C5A—C6A—C7A—C8A	155.6 (5)
C19—C14—C15—C16	58.6 (6)	C1A—C6A—C7A—C8A	−19.8 (7)
C17—C16—C15—C14	−54.5 (6)	N1A—C8A—C7A—C6A	51.7 (6)
C20—O3—C17—C18	158.3 (5)	C14A—C19A—C18A—C17A	57.1 (7)
C20—O3—C17—C16	−79.2 (6)	C19A—C18A—C17A—O3B	76.0 (9)
C15—C16—C17—O3	−67.5 (6)	C19A—C18A—C17A—O3A	58.9 (7)
C15—C16—C17—C18	51.9 (7)	C19A—C18A—C17A—C16A	−56.7 (7)
C2—C1—C6—C5	−3.4 (8)	C15A—C16A—C17A—O3B	−51.0 (13)
C12—C1—C6—C5	177.8 (5)	C15A—C16A—C17A—O3A	−69.6 (6)
C2—C1—C6—C7	174.3 (5)	C15A—C16A—C17A—C18A	54.8 (7)
C12—C1—C6—C7	−4.5 (8)	C1A—C2A—C3A—C4A	0.6 (8)
C8—C7—C6—C5	156.6 (5)	C5A—C4A—C3A—C2A	−0.7 (8)
C8—C7—C6—C1	−21.0 (7)	C22A—C21A—C26A—C25A	−3.8 (19)
O3—C17—C18—C19	68.3 (6)	C20A—C21A—C26A—C25A	175.5 (9)
C16—C17—C18—C19	−53.6 (6)	C22A—C21A—C26A—C21B	96 (15)
C14—C19—C18—C17	58.2 (6)	C20A—C21A—C26A—C21B	−85 (14)
C9—N1—C8—C7	124.8 (5)	C22A—C23A—C24A—C25A	−1.1 (11)
C12—N1—C8—C7	−63.1 (6)	C23A—C24A—C25A—C26A	0.6 (10)
C6—C7—C8—N1	52.4 (6)	C21A—C26A—C25A—C24A	1.9 (13)
C1—C6—C5—C4	3.5 (8)	C21B—C26A—C25A—C24A	−6 (3)
C7—C6—C5—C4	−174.2 (5)	C24A—C23A—C22A—C21B	7 (3)
C23—C22—C21—C26	−2.3 (9)	C24A—C23A—C22A—C21A	−0.6 (13)
C23—C22—C21—C20	173.4 (6)	C26A—C21A—C22A—C23A	3.1 (19)
C1—C2—C3—C4	−0.8 (8)	C20A—C21A—C22A—C23A	−176.2 (10)
C21—C22—C23—C24	0.7 (10)	C26A—C21A—C22A—C21B	−113 (17)
C17—O3—C20—C21	173.5 (5)	C20A—C21A—C22A—C21B	68 (15)
C26—C21—C20—O3	−9.0 (9)	O3B—C17A—O3A—C20A	37.7 (15)
C22—C21—C20—O3	175.5 (5)	C18A—C17A—O3A—C20A	70.7 (8)
C22—C21—C26—C25	2.0 (9)	C16A—C17A—O3A—C20A	−169.1 (6)
C20—C21—C26—C25	−173.4 (6)	C17A—O3A—C20A—C21A	172.9 (6)
C21—C26—C25—C24	0.0 (9)	C26A—C21A—C20A—O3A	88.9 (14)
C2—C3—C4—C5	0.8 (8)	C22A—C21A—C20A—O3A	−91.8 (14)
C6—C5—C4—C3	−2.2 (9)	O3A—C17A—O3B—C20B	−50.1 (17)
C26—C25—C24—C23	−1.6 (10)	C18A—C17A—O3B—C20B	159.1 (16)
C22—C23—C24—C25	1.3 (10)	C16A—C17A—O3B—C20B	−85.4 (18)
C14A—C15A—C16A—C17A	−54.9 (7)	C17A—O3B—C20B—C21B	164 (3)
C10A—N2A—C13A—O2A	3.7 (8)	C23A—C22A—C21B—C26A	−12 (6)
C11A—N2A—C13A—O2A	177.6 (5)	C21A—C22A—C21B—C26A	56 (12)
C10A—N2A—C13A—C14A	−179.0 (5)	C23A—C22A—C21B—C20B	166.3 (18)
C11A—N2A—C13A—C14A	−5.1 (8)	C21A—C22A—C21B—C20B	−126 (19)
C13A—N2A—C10A—C9A	−147.8 (5)	C21A—C26A—C21B—C22A	−73 (12)
C11A—N2A—C10A—C9A	37.5 (7)	C25A—C26A—C21B—C22A	11 (6)
C13A—N2A—C11A—C12A	126.6 (5)	C21A—C26A—C21B—C20B	110 (21)
C10A—N2A—C11A—C12A	−59.2 (6)	C25A—C26A—C21B—C20B	−165 (7)
C8A—N1A—C9A—O1A	−1.6 (8)	O3B—C20B—C21B—C22A	179 (3)
C12A—N1A—C9A—O1A	−173.9 (5)	O3B—C20B—C21B—C26A	−4 (10)
C8A—N1A—C9A—C10A	179.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2ⁱ	0.99	2.45	3.332 (7)	149
C20A—H20C···O2Aⁱⁱ	0.99	2.60	3.567 (10)	165
C20B—H20F···O2Aⁱⁱ	0.99	2.26	3.19 (3)	156

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2ⁱ	0.99	2.45	3.332 (7)	148.5
C20A—H20C···O2Aⁱⁱ	0.99	2.60	3.567 (10)	164.5
C20B—H20F···O2Aⁱⁱ	0.99	2.26	3.19 (3)	156.3

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

Acknowledgements

AC-C is grateful to CONACyT for a graduate student scholarship. The authors acknowledge M. Flores-Alamo for the data collection.

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