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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1242-o1243
doi:10.1107/S160053680901650X

4-{[(E)-(4-Chloro­phen­yl)methyl­­idene]amino}-3-{2-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,a*‡ Samuel Robinson Jebas,a§ K. V Sujithb and Balakrishna Kallurayab

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 25 April 2009; accepted 2 May 2009; online 14 May 2009)

The asymmetric unit of the title compound, C21H23ClN4S, contains nine crystallographically independent mol­ecules, labelled A to I. The orientation of the 2-[4-(2-methyl­prop­yl)phen­yl]ethyl unit with respect to the rest of the mol­ecule is significantly different in mol­ecules E, F, H and I compared to the other independent mol­ecules. The isobutyl group of mol­ecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chloro­phenyl and methyl­propyl­phenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in mol­ecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent mol­ecule, a C—H⋯S hydrogen bond is observed. The crystal packing is stabilized by N—H⋯S and C—H⋯S hydrogen bonds, and by C—H⋯π inter­actions involving the methyl­propyl­phenyl ring.

Related literature

For the activity of ibuprofen, see: Amir & Kumar (2007[Amir, M. & Kumar, S. (2007). Acta Pharm. 57, 31-45.]). For the activity of 1,2,4-triazol-5-one compounds, see: Demirbas et al. (2002[Demirbas, N., Ugurluoglu, R. & Demirbasx, A. (2002). Bioorg. Med. Chem. 10, 3717-3723.], 2004[Demirbas, N., Alpay-Karaoglu, S., Demirbas, A. & Sancak, K. (2004). Eur. J. Med. Chem. 39, 793-804.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]). For related structures, see: Fun et al. (2008a[Fun, H.-K., Jebas, S. R., Razak, I. A., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008a). Acta Cryst. E64, o1076-o1077.],b[Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008b). Acta Cryst. E64, o1001-o1002.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C21H23ClN4S

  • Mr = 398.94

  • Triclinic, [P \overline 1]

  • a = 13.1781 (2) Å

  • b = 23.7731 (4) Å

  • c = 30.8550 (5) Å

  • α = 92.861 (1)°

  • β = 101.520 (1)°

  • γ = 92.254 (1)°

  • V = 9447.8 (3) Å3

  • Z = 18

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 100 K

  • 0.55 × 0.34 × 0.13 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.855, Tmax = 0.962

  • 157626 measured reflections

  • 38430 independent reflections

  • 27090 reflections with I > 2σ(I)

  • Rint = 0.044
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.139

  • S = 1.01

  • 38430 reflections

  • 2230 parameters

  • 71 restraints

  • H-atom parameters constrained

  • Δρmax = 0.84 e Å−3

  • Δρmin = −0.63 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1AB⋯S1Fi 0.86 2.52 3.373 (2) 170
N1B—H1BB⋯S1Cii 0.86 2.47 3.3072 (19) 163
N1C—H1CB⋯S1Biii 0.86 2.45 3.285 (2) 165
N1D—H1DB⋯S1Eiv 0.86 2.48 3.3289 (19) 171
N1E—H1EB⋯S1Dv 0.86 2.41 3.253 (2) 168
N1F—H1FB⋯S1Ai 0.86 2.41 3.256 (2) 167
N1G—H1GB⋯S1Hiv 0.86 2.43 3.287 (2) 174
N1H—H1HB⋯S1Gv 0.86 2.45 3.3047 (19) 170
N1I—H1IB⋯S1Ivi 0.86 2.45 3.301 (2) 172
C10D—H10D⋯S1Civ 0.98 2.87 3.769 (2) 152
C10G—H10G⋯S1Fiv 0.98 2.82 3.662 (2) 144
C7A—H7AA⋯S1A 0.93 2.58 3.174 (2) 122
C7B—H7BA⋯S1B 0.93 2.57 3.240 (2) 130
C7C—H7CA⋯S1C 0.93 2.58 3.254 (2) 130
C7D—H7DA⋯S1D 0.93 2.59 3.174 (2) 121
C7E—H7EA⋯S1E 0.93 2.56 3.223 (2) 129
C7F—H7FA⋯S1F 0.93 2.56 3.229 (2) 130
C7G—H7GA⋯S1G 0.93 2.61 3.178 (2) 120
C7H—H7HA⋯S1H 0.93 2.55 3.187 (2) 126
C7I—H7IA⋯S1I 0.93 2.61 3.179 (2) 120
C4D—H4DA⋯Cg1 0.93 2.72 3.588 (2) 156
C4E—H4EA⋯Cg2 0.93 2.84 3.566 (3) 136
C4G—H4GA⋯Cg3 0.93 2.86 3.701 (2) 152
C4H—H4HA⋯Cg4 0.93 2.51 3.338 (2) 148
C4A—H4AA⋯Cg5vi 0.93 2.72 3.606 (2) 159
C4C—H4CA⋯Cg6vii 0.93 2.96 3.670 (2) 134
C4F—H4FA⋯Cg7vi 0.93 2.78 3.524 (3) 137
C4I—H4IA⋯Cg8viii 0.93 2.88 3.719 (2) 151
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x+1, y+1, z; (iii) x-1, y-1, z; (iv) x+1, y, z; (v) x-1, y, z; (vi) -x+1, -y+1, -z+1; (vii) x, y-1, z; (viii) -x+2, -y+1, -z+1. Cg1 is the centroid of the N1/C2–C5 ring.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901650X/ci2794sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901650X/ci2794Isup2.hkl

checkCIF report


Comment top

1,2,4-Triazoles and their derivatives represent an overwhelming and rapid developing field in modern heterocyclic chemistry. Similarly, ibuprofen belongs to the class of non-steroidal anti-inflammatory drugs (NSAIDs) with antipyretic, anti-inflammatory and analgesic properties (Amir & Kumar, 2007). Our earlier studies involved synthesis of heterocyclic compounds containing in their structures both the ibuprofen and 1,2,4-triazole fragments (Fun et al., 2008a,b). Schiff base derivatives of 1,2,4-triazol-5-ones are found to possess antitumor activity (Demirbas et al., 2004). Some Schiff base derivatives of acetic acid hydrazides containing 1,2,4-triazol-5-one ring have displayed antitumoral activity against breast cancer, while 2-phenyl ethylidenamino and 2-phenyl ethylamino derivatives of 4-amino-1,2,4-triazol-5-ones have been found to be effective towards non-small cell lung cancer, CNC and breast cancer (Demirbas et al., 2002). In this connection and in continuation of our interest in the synthesis of chemically and biologically important heterocycles, we now report the title compound which is a substituted 1,2,4-triazole Schiff base carrying ibuprofen moiety.

The asymmetric unit of the title compound (Fig. 1) contains nine crystallographically independent molecules (say A to I; their atoms are labelled with suffixes A to I). The orientation of the 1-[4-(2-methylpropyl)phenyl]ethyl unit with respect to the rest of the molecule is different in some of these molecules. This is indicated by the C(H3)—C···C—C(H2) i.e. the C21—C10···C17—C18 torsion angle of -10.8 (2), 3.2 (2), 7.0 (2), -2.1 (2), 151.60 (18), 156.32 (18), 42.1 (3), 154.01 (18) and 156.10 (18)°, respectively, in molecules A, B, C, D, E, F, G, H and I. This is also clearly shown in a superimposed fit (Fig. 3) of molecule A (solid) and other molecules (dashed lines). Bond lengths (Allen et al., 1987) and angles are normal. The isobutyl group of the molecule B is disordered over two orientations with occupancies of 0.764 (7) and 0.236 (7). The C1–C6 and C11–C16 benzene rings form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in molecule A [9.15 (11)° and 80.37 (11)° in B, 7.14 (11)° and 84.06 (11)° in C, 25.76 (11)° and 76.59 (11)° in D, 13.68 (11)° and 76.82 (10)° in E, 8.38 (11)° and 69.77 (10)° in F, 30.34 (11)° and 78.12 (11)° in G, 21.20 (11)° and 71.58 (10)° in H, and 27.65 (11)° and 65.23 (11)° in molecule I]. In six of the molecules, the C1–C6 and C11–C16 benzene rings are almost perpendicular to each other [dihedral angles are: 87.65 (10)° (A), 89.42 (10)° (B), 89.02 (10)° (C), 89.52 (10) (E), 87.24 (10)° (H) and 87.15 (10)° (I)]. The dihedral angle between the two benzene rings in the other three molecules are 79.74 (10)° (D), 78.13 (10)° (F), and 74.11 (10)° (G). In each independent molecule a C—H···S hydrogen bond is observed (Bernstein et al., 1995).

The crystal packing is stabilized by N—H···S and C—H···S hydrogen bonds, and C—H···π interactions involving the methylpropylphenyl ring.

Related literature top

For the activity of ibuprofen, see: Amir & Kumar (2007). For the activity of 1,2,4-triazol-5-one compounds, see: Demirbas et al. (2002, 2004). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2008a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the N1/C2–C5 ring.

Experimental top

The title compound, a Schiff base, was obtained by refluxing 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,2,4-triazole-3-thiol (0.01 mol) and 4-chlorobenzaldehyde (0.01 mol) in ethanol (50 ml) by adding 3 drops of concentrated sulfuric acid for 3 h. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol–N,N-dimethylformamide (3:1) solution.

Refinement top

H atoms were positioned geometrically [C—H = 0.93–0.98 Å and N—H = 0.86 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C, N) and 1.5Ueq(methyl C). A rotating group model was used for the methyl groups. The methylpropyl unit of molecule B is disordered over two sites with occupancies of 0.764 (7) and 0.236 (7).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom numbering scheme of molecule A and molecule B. For clarity labelling is not shown for the remaining seven molecules.
[Figure 2] Fig. 2. One of the nine independent molecules in the asymmertic unit to show clearly the atomic labelling. The other eight molecules are labelled in a similar manner.
[Figure 3] Fig. 3. Superimposed fit of molecule A (solid lines) and molecules B to I (dashed lines).
4-{[(E)-(4-Chlorophenyl)methylidene]amino}-5-{2-[4-(2-methylpropyl)phenyl]ethyl}-4H-1,2,4-triazole-3-thiol top
Crystal data top
C21H23ClN4SZ = 18
Mr = 398.94F(000) = 3780
Triclinic, P1Dx = 1.262 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.1781 (2) ÅCell parameters from 9483 reflections
b = 23.7731 (4) Åθ = 2.4–30.9°
c = 30.8550 (5) ŵ = 0.29 mm−1
α = 92.861 (1)°T = 100 K
β = 101.520 (1)°Block, colourless
γ = 92.254 (1)°0.55 × 0.34 × 0.13 mm
V = 9447.8 (3) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		38430 independent reflections
Radiation source: fine-focus sealed tube27090 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ϕ and ω scansθmax = 26.5°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −16→14
Tmin = 0.855, Tmax = 0.962k = −29→29
157626 measured reflectionsl = −38→38
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0694P)2 + 3.1587P]
where P = (Fo2 + 2Fc2)/3
38430 reflections(Δ/σ)max = 0.001
2230 parametersΔρmax = 0.84 e Å−3
71 restraintsΔρmin = −0.63 e Å−3
Crystal data top
C21H23ClN4Sγ = 92.254 (1)°
Mr = 398.94V = 9447.8 (3) Å3
Triclinic, P1Z = 18
a = 13.1781 (2) ÅMo Kα radiation
b = 23.7731 (4) ŵ = 0.29 mm−1
c = 30.8550 (5) ÅT = 100 K
α = 92.861 (1)°0.55 × 0.34 × 0.13 mm
β = 101.520 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		38430 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		27090 reflections with I > 2σ(I)
Tmin = 0.855, Tmax = 0.962Rint = 0.044
157626 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04671 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.01Δρmax = 0.84 e Å−3
38430 reflectionsΔρmin = −0.63 e Å−3
2230 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > σ(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
xyzUiso*/UeqOcc. (<1)
Cl1A0.85383 (5)0.82060 (3)0.703247 (19)0.03750 (15)
S1A0.25870 (5)0.80270 (2)0.780325 (18)0.02729 (13)
N1A0.23128 (14)0.88548 (7)0.84039 (6)0.0237 (4)
H1AB0.17240.87110.84340.028*
N2A0.27375 (14)0.93578 (7)0.86153 (6)0.0246 (4)
N3A0.37677 (13)0.89701 (7)0.82143 (5)0.0202 (4)
N4A0.46114 (14)0.89728 (7)0.80031 (5)0.0211 (4)
C1A0.64370 (17)0.88998 (9)0.76293 (7)0.0231 (5)
H1AA0.63000.92580.77320.028*
C2A0.72680 (17)0.88322 (9)0.74275 (7)0.0262 (5)
H2AA0.76930.91410.73930.031*
C3A0.74637 (18)0.82949 (9)0.72757 (7)0.0260 (5)
C4A0.68417 (18)0.78280 (9)0.73183 (7)0.0267 (5)
H4AA0.69790.74720.72120.032*
C5A0.60083 (18)0.79017 (9)0.75234 (7)0.0246 (5)
H5AA0.55850.75910.75560.030*
C6A0.57929 (16)0.84360 (8)0.76826 (6)0.0202 (4)
C7A0.49208 (17)0.84877 (9)0.79050 (6)0.0223 (5)
H7AA0.45850.81640.79770.027*
C8A0.28930 (17)0.86102 (9)0.81480 (6)0.0217 (5)
C9A0.36170 (17)0.94227 (8)0.84916 (7)0.0213 (5)
C10A0.43785 (17)0.99199 (8)0.86148 (7)0.0224 (5)
H10A0.46491.00070.83510.027*
C11A0.52965 (17)0.97921 (8)0.89767 (7)0.0220 (5)
C12A0.51540 (18)0.96624 (9)0.93983 (7)0.0249 (5)
H12A0.44880.96320.94560.030*
C13A0.60008 (18)0.95797 (9)0.97309 (7)0.0278 (5)
H13A0.58920.94951.00100.033*
C14A0.70079 (18)0.96204 (9)0.96593 (7)0.0288 (5)
C15A0.71414 (18)0.97422 (9)0.92368 (7)0.0295 (5)
H15A0.78080.97700.91800.035*
C16A0.63030 (18)0.98220 (9)0.89010 (7)0.0262 (5)
H16A0.64130.98970.86200.031*
C17A0.7925 (2)0.95564 (10)1.00328 (8)0.0371 (6)
H17A0.78000.92191.01830.045*
H17B0.85360.95040.99080.045*
C18A0.8142 (2)1.00507 (11)1.03694 (8)0.0423 (7)
H18A0.75321.00751.05050.051*
C19A0.9063 (2)0.99401 (14)1.07425 (10)0.0664 (10)
H19A0.91621.02471.09640.100*
H19B0.96780.99091.06230.100*
H19C0.89220.95951.08740.100*
C20A0.8294 (3)1.06006 (12)1.01865 (11)0.0753 (11)
H20A0.77001.06680.99630.113*
H20B0.89011.05991.00580.113*
H20C0.83821.08931.04190.113*
C21A0.38360 (18)1.04385 (9)0.87514 (7)0.0296 (5)
H21A0.32941.05260.85100.044*
H21B0.43301.07530.88250.044*
H21C0.35441.03610.90050.044*
Cl1B−0.13778 (5)0.99741 (3)0.82181 (2)0.03966 (16)
S1B0.48175 (5)1.06825 (2)0.758803 (18)0.02621 (13)
N1B0.51925 (14)0.98842 (7)0.69898 (5)0.0238 (4)
H1BB0.57651.00520.69630.029*
N2B0.48270 (14)0.93719 (7)0.67713 (6)0.0245 (4)
N3B0.37483 (13)0.97019 (7)0.71727 (5)0.0198 (4)
N4B0.28658 (13)0.96490 (7)0.73551 (5)0.0208 (4)
C1B0.09189 (17)0.95660 (8)0.76112 (7)0.0231 (5)
H1BA0.11020.92540.74550.028*
C2B0.00098 (18)0.95409 (9)0.77678 (7)0.0262 (5)
H2BA−0.04250.92170.77140.031*
C3B−0.02473 (18)1.00067 (10)0.80065 (7)0.0266 (5)
C4B0.03792 (19)1.04946 (9)0.80802 (7)0.0292 (5)
H4BA0.01981.08040.82400.035*
C5B0.12753 (18)1.05204 (9)0.79153 (7)0.0261 (5)
H5BA0.16911.08520.79590.031*
C6B0.15686 (17)1.00537 (8)0.76832 (6)0.0211 (5)
C7B0.25204 (17)1.00978 (9)0.75097 (6)0.0220 (5)
H7BA0.28711.04450.75110.026*
C8B0.45772 (17)1.00959 (8)0.72473 (6)0.0216 (5)
C9B0.39551 (17)0.92678 (8)0.68903 (6)0.0210 (5)
C10B0.32423 (16)0.87562 (8)0.67458 (7)0.0227 (5)
H10B0.30050.86230.70060.027*
C11B0.22964 (17)0.89028 (8)0.64081 (7)0.0213 (5)
C12B0.24070 (17)0.91431 (9)0.60174 (7)0.0243 (5)
H12B0.30670.92240.59660.029*
C13B0.15441 (18)0.92629 (9)0.57037 (7)0.0264 (5)
H13B0.16360.94240.54450.032*
C14B0.05462 (18)0.91472 (9)0.57686 (7)0.0270 (5)
C15B0.04343 (18)0.89046 (9)0.61604 (7)0.0300 (5)
H15B−0.02260.88220.62120.036*
C16B0.13016 (17)0.87850 (9)0.64746 (7)0.0253 (5)
H16B0.12120.86230.67340.030*
C17B−0.03791 (19)0.92605 (10)0.54174 (8)0.0358 (6)
H17C−0.03150.96470.53360.043*0.764 (7)
H17Q−0.10000.92210.55400.043*0.764 (7)
H17R−0.01450.94850.52030.043*0.236 (7)
H17S−0.08350.94830.55540.043*0.236 (7)
C18B−0.0503 (3)0.88723 (13)0.50063 (10)0.0308 (10)0.764 (7)
H18B0.00620.89890.48610.037*0.764 (7)
C19B−0.0382 (4)0.8256 (2)0.50700 (19)0.0389 (12)0.764 (7)
H19D0.03030.81990.52330.058*0.764 (7)
H19E−0.04890.80530.47860.058*0.764 (7)
H19F−0.08840.81200.52320.058*0.764 (7)
C20B−0.1495 (4)0.8974 (2)0.46773 (15)0.0476 (12)0.764 (7)
H20D−0.15190.87500.44080.071*0.764 (7)
H20E−0.15090.93660.46150.071*0.764 (7)
H20F−0.20840.88720.48020.071*0.764 (7)
C18X−0.0996 (8)0.8745 (4)0.5164 (3)0.017 (3)*0.236 (7)
H18J−0.14470.86580.53720.020*0.236 (7)
C19X−0.0640 (16)0.8310 (9)0.5134 (7)0.037 (5)*0.236 (7)
H19G−0.06300.81190.54020.055*0.236 (7)
H19H0.00550.83630.50870.055*0.236 (7)
H19I−0.10510.80870.48880.055*0.236 (7)
C20X−0.1838 (12)0.8951 (7)0.4767 (5)0.031 (3)*0.236 (7)
H20G−0.23310.86450.46510.046*0.236 (7)
H20H−0.15010.90740.45380.046*0.236 (7)
H20I−0.21910.92580.48740.046*0.236 (7)
C21B0.38263 (17)0.82869 (9)0.65628 (7)0.0277 (5)
H21D0.44020.81950.67870.041*
H21E0.40760.84120.63100.041*
H21F0.33680.79590.64760.041*
Cl1C0.38051 (5)0.10472 (3)0.632486 (19)0.03874 (15)
S1C−0.23891 (4)0.02693 (2)0.695205 (17)0.02521 (13)
N1C−0.28244 (14)0.11008 (7)0.75088 (5)0.0232 (4)
H1CB−0.33880.09280.75410.028*
N2C−0.24996 (14)0.16287 (7)0.77044 (6)0.0244 (4)
N3C−0.13860 (13)0.12876 (7)0.73237 (5)0.0199 (4)
N4C−0.04987 (13)0.13417 (7)0.71452 (5)0.0201 (4)
C1C0.14639 (17)0.14414 (9)0.69089 (7)0.0234 (5)
H1CA0.12630.17530.70590.028*
C2C0.23754 (17)0.14752 (9)0.67526 (7)0.0261 (5)
H2CA0.27890.18070.67970.031*
C3C0.26654 (17)0.10072 (10)0.65291 (7)0.0261 (5)
C4C0.20609 (18)0.05100 (9)0.64595 (7)0.0279 (5)
H4CA0.22610.02010.63060.033*
C5C0.11595 (18)0.04784 (9)0.66201 (7)0.0248 (5)
H5CA0.07570.01420.65790.030*
C6C0.08405 (16)0.09423 (8)0.68433 (6)0.0203 (5)
C7C−0.01182 (16)0.08933 (8)0.70132 (6)0.0212 (5)
H7CA−0.04450.05420.70250.025*
C8C−0.21894 (17)0.08805 (8)0.72646 (7)0.0212 (5)
C9C−0.16298 (17)0.17350 (8)0.75831 (6)0.0204 (5)
C10C−0.09444 (17)0.22588 (8)0.77116 (7)0.0224 (5)
H10C−0.07220.23850.74460.027*
C11C0.00160 (17)0.21418 (8)0.80516 (7)0.0226 (5)
C12C−0.00735 (18)0.18729 (9)0.84341 (7)0.0254 (5)
H12C−0.07260.17540.84770.030*
C13C0.07946 (18)0.17800 (9)0.87509 (7)0.0286 (5)
H13C0.07160.15990.90030.034*
C14C0.17827 (18)0.19510 (9)0.87012 (7)0.0307 (5)
C15C0.18699 (19)0.22212 (10)0.83171 (7)0.0336 (6)
H15C0.25220.23400.82750.040*
C16C0.09996 (18)0.23145 (10)0.79982 (7)0.0298 (5)
H16C0.10760.24950.77450.036*
C17C0.2725 (2)0.18702 (11)0.90596 (8)0.0385 (6)
H17D0.33440.19830.89540.046*
H17E0.27590.14730.91160.046*
C18C0.2714 (2)0.22064 (11)0.94913 (8)0.0395 (6)
H18C0.21540.20420.96180.047*
C19C0.2511 (2)0.28123 (10)0.94309 (8)0.0358 (6)
H19J0.18240.28430.92600.054*
H19K0.30070.29760.92780.054*
H19L0.25710.30080.97150.054*
C20C0.3740 (2)0.21397 (12)0.98213 (9)0.0560 (8)
H20J0.37190.23361.00990.084*
H20K0.43060.22950.97050.084*
H20L0.38340.17470.98660.084*
C21C−0.15519 (17)0.27256 (9)0.78850 (7)0.0273 (5)
H21G−0.21450.27970.76610.041*
H21H−0.11150.30640.79570.041*
H21I−0.17780.26090.81450.041*
Cl1D0.37045 (5)0.28423 (3)0.74544 (2)0.04183 (16)
S1D0.96227 (5)0.30506 (2)0.666660 (19)0.02873 (14)
N1D0.99868 (14)0.21702 (7)0.61318 (6)0.0242 (4)
H1DB1.05720.23160.60980.029*
N2D0.95998 (14)0.16449 (7)0.59513 (6)0.0239 (4)
N3D0.85226 (13)0.20589 (7)0.63133 (5)0.0192 (4)
N4D0.76695 (13)0.20644 (7)0.65203 (5)0.0204 (4)
C1D0.58706 (17)0.21390 (9)0.69013 (7)0.0234 (5)
H1DA0.60550.17770.68310.028*
C2D0.50422 (18)0.22107 (9)0.71066 (7)0.0274 (5)
H2DA0.46750.18990.71800.033*
C3D0.47642 (18)0.27519 (10)0.72026 (7)0.0271 (5)
C4D0.53066 (19)0.32223 (9)0.71050 (7)0.0292 (5)
H4DA0.51140.35830.71740.035*
C5D0.61388 (18)0.31474 (9)0.69028 (7)0.0261 (5)
H5DA0.65090.34610.68350.031*
C6D0.64357 (17)0.26058 (8)0.67978 (6)0.0216 (5)
C7D0.73190 (17)0.25500 (9)0.65830 (7)0.0231 (5)
H7DA0.76290.28690.64910.028*
C8D0.93738 (17)0.24321 (8)0.63626 (7)0.0221 (5)
C9D0.87164 (17)0.15822 (8)0.60703 (7)0.0207 (5)
C10D0.79832 (17)0.10732 (8)0.59684 (7)0.0219 (5)
H10D0.77500.09880.62420.026*
C11D0.70285 (16)0.11824 (8)0.56214 (7)0.0205 (5)
C12D0.71159 (17)0.13153 (9)0.51955 (7)0.0245 (5)
H12D0.77680.13550.51260.029*
C13D0.62404 (18)0.13894 (9)0.48753 (7)0.0259 (5)
H13D0.63160.14830.45940.031*
C14D0.52500 (17)0.13275 (8)0.49657 (7)0.0237 (5)
C15D0.51685 (17)0.11976 (9)0.53907 (7)0.0252 (5)
H15D0.45160.11550.54600.030*
C16D0.60436 (17)0.11306 (8)0.57150 (7)0.0234 (5)
H16D0.59690.10500.59990.028*
C17D0.42990 (18)0.13953 (10)0.46129 (7)0.0306 (5)
H17F0.43300.17740.45110.037*
H17G0.36930.13600.47460.037*
C18D0.4155 (2)0.09812 (10)0.42165 (8)0.0373 (6)
H18D0.47420.10510.40720.045*
C19D0.3172 (2)0.10925 (12)0.38805 (9)0.0489 (7)
H19M0.31880.14810.38090.073*
H19N0.25750.10110.40050.073*
H19O0.31370.08560.36160.073*
C20D0.4168 (3)0.03784 (11)0.43289 (10)0.0654 (10)
H20M0.48240.03100.45140.098*
H20N0.40670.01410.40610.098*
H20O0.36210.02970.44840.098*
C21D0.85355 (18)0.05629 (9)0.58289 (7)0.0284 (5)
H21J0.91290.05020.60560.043*
H21K0.87560.06300.55570.043*
H21L0.80690.02350.57860.043*
Cl1E0.83044 (5)0.32101 (4)0.52096 (2)0.0523 (2)
S1E0.23746 (4)0.26006 (2)0.605360 (18)0.02509 (13)
N1E0.18327 (14)0.35298 (7)0.64801 (6)0.0245 (4)
H1EB0.12990.33580.65430.029*
N2E0.20849 (14)0.40927 (7)0.65912 (6)0.0243 (4)
N3E0.32237 (13)0.36989 (7)0.62506 (5)0.0191 (4)
N4E0.40700 (13)0.37266 (7)0.60432 (5)0.0204 (4)
C1E0.59372 (17)0.37713 (9)0.57074 (7)0.0254 (5)
H1EA0.56850.41170.57780.031*
C2E0.68195 (18)0.37577 (10)0.55298 (7)0.0308 (5)
H2EA0.71660.40900.54820.037*
C3E0.71792 (18)0.32367 (11)0.54239 (7)0.0316 (6)
C4E0.66797 (19)0.27400 (10)0.54895 (7)0.0340 (6)
H4EA0.69290.23960.54130.041*
C5E0.58016 (18)0.27578 (9)0.56701 (7)0.0281 (5)
H5EA0.54610.24230.57170.034*
C6E0.54213 (16)0.32738 (9)0.57820 (6)0.0206 (5)
C7E0.45121 (17)0.32657 (8)0.59876 (7)0.0216 (5)
H7EA0.42580.29290.60770.026*
C8E0.24898 (17)0.32730 (8)0.62652 (7)0.0214 (5)
C9E0.29259 (16)0.41873 (8)0.64459 (6)0.0203 (5)
C10E0.35474 (16)0.47371 (8)0.64964 (7)0.0205 (5)
H10E0.38200.47820.62260.025*
C11E0.44614 (16)0.47289 (8)0.68857 (7)0.0193 (4)
C12E0.42888 (17)0.47057 (8)0.73171 (7)0.0239 (5)
H12E0.36130.46870.73640.029*
C13E0.51114 (18)0.47104 (8)0.76738 (7)0.0249 (5)
H13E0.49790.47000.79580.030*
C14E0.61355 (17)0.47297 (8)0.76179 (7)0.0222 (5)
C15E0.63021 (17)0.47492 (9)0.71866 (7)0.0242 (5)
H15E0.69770.47630.71390.029*
C16E0.54792 (17)0.47485 (8)0.68273 (7)0.0225 (5)
H16E0.56120.47610.65430.027*
C17E0.70236 (18)0.47314 (9)0.80112 (7)0.0288 (5)
H17H0.67970.48900.82700.035*
H17I0.75850.49770.79580.035*
C18E0.74432 (17)0.41484 (9)0.81149 (7)0.0267 (5)
H18E0.76400.39820.78480.032*
C19E0.84109 (19)0.42163 (11)0.84840 (8)0.0375 (6)
H19P0.86930.38540.85390.056*
H19Q0.82300.43750.87490.056*
H19R0.89180.44630.83960.056*
C20E0.66371 (19)0.37535 (9)0.82456 (7)0.0304 (5)
H20P0.60360.37120.80100.046*
H20Q0.64440.39070.85100.046*
H20R0.69210.33920.83000.046*
C21E0.28509 (17)0.52254 (9)0.65482 (7)0.0265 (5)
H21M0.23090.52270.62890.040*
H21N0.32560.55750.65840.040*
H21O0.25510.51800.68040.040*
Cl1F0.61591 (5)0.22275 (3)0.07918 (2)0.04443 (17)
S1F0.01418 (5)0.15690 (2)0.156284 (18)0.02538 (13)
N1F−0.03279 (14)0.24510 (7)0.20618 (6)0.0230 (4)
H1FB−0.08730.22760.21120.028*
N2F−0.00403 (14)0.29996 (7)0.22143 (6)0.0237 (4)
N3F0.10801 (13)0.26323 (7)0.18493 (5)0.0191 (4)
N4F0.19458 (13)0.26727 (7)0.16541 (5)0.0203 (4)
C1F0.38710 (17)0.27321 (9)0.13664 (7)0.0229 (5)
H1FA0.36700.30670.14860.028*
C2F0.47581 (17)0.27338 (9)0.11922 (7)0.0262 (5)
H2FA0.51570.30660.11950.031*
C3F0.50449 (18)0.22315 (10)0.10123 (7)0.0274 (5)
C4F0.44603 (18)0.17331 (10)0.10040 (7)0.0290 (5)
H4FA0.46560.14010.08790.035*
C5F0.35829 (17)0.17378 (9)0.11835 (7)0.0252 (5)
H5FA0.31920.14030.11830.030*
C6F0.32706 (16)0.22344 (8)0.13659 (6)0.0204 (5)
C7F0.23444 (16)0.22115 (8)0.15585 (6)0.0209 (5)
H7FA0.20480.18660.16110.025*
C8F0.03097 (16)0.22131 (8)0.18287 (6)0.0207 (5)
C9F0.08118 (17)0.31028 (8)0.20781 (6)0.0208 (5)
C10F0.14413 (16)0.36518 (8)0.21492 (7)0.0210 (5)
H10F0.17320.37070.18850.025*
C11F0.23369 (16)0.36485 (8)0.25454 (7)0.0197 (4)
C12F0.21410 (17)0.36079 (9)0.29701 (7)0.0235 (5)
H12F0.14610.35620.30090.028*
C13F0.29481 (17)0.36354 (9)0.33353 (7)0.0243 (5)
H13F0.27990.36100.36160.029*
C14F0.39763 (17)0.36997 (8)0.32934 (7)0.0223 (5)
C15F0.41655 (17)0.37352 (9)0.28657 (7)0.0238 (5)
H15F0.48460.37770.28270.029*
C16F0.33629 (17)0.37100 (8)0.24988 (7)0.0225 (5)
H16F0.35110.37340.22180.027*
C17F0.48446 (18)0.37296 (9)0.36946 (7)0.0286 (5)
H17J0.45760.38600.39510.034*
H17K0.53700.40070.36530.034*
C18F0.53579 (18)0.31678 (10)0.37932 (7)0.0293 (5)
H18F0.55960.30300.35280.035*
C19F0.6300 (2)0.32591 (12)0.41714 (8)0.0424 (7)
H19S0.66260.29080.42250.064*
H19T0.60830.33980.44340.064*
H19U0.67840.35290.40930.064*
C20F0.46005 (19)0.27271 (10)0.39009 (8)0.0334 (6)
H20S0.40260.26640.36550.050*
H20T0.43520.28560.41590.050*
H20U0.49420.23810.39570.050*
C21F0.07324 (17)0.41368 (9)0.22009 (7)0.0260 (5)
H21P0.01970.41400.19400.039*
H21Q0.11330.44890.22420.039*
H21R0.04240.40850.24540.039*
Cl1G0.58511 (5)0.40958 (3)0.18862 (2)0.04281 (16)
S1G1.16825 (4)0.42348 (2)0.104365 (18)0.02504 (13)
N1G1.21206 (14)0.32959 (7)0.05923 (6)0.0233 (4)
H1GB1.26980.34420.05500.028*
N2G1.17793 (14)0.27500 (7)0.04536 (6)0.0231 (4)
N3G1.06574 (13)0.31906 (7)0.07773 (5)0.0185 (4)
N4G0.98101 (13)0.32122 (7)0.09861 (5)0.0203 (4)
C1G0.80628 (17)0.33359 (9)0.14017 (7)0.0240 (5)
H1GA0.82920.29730.13790.029*
C2G0.72490 (18)0.34339 (9)0.16089 (7)0.0263 (5)
H2GA0.69360.31410.17310.032*
C3G0.68998 (18)0.39769 (9)0.16335 (7)0.0272 (5)
C4G0.73655 (18)0.44226 (9)0.14642 (7)0.0287 (5)
H4GA0.71290.47840.14870.034*
C5G0.81881 (18)0.43217 (9)0.12609 (7)0.0253 (5)
H5GA0.85080.46190.11460.030*
C6G0.85492 (16)0.37790 (9)0.12243 (6)0.0214 (5)
C7G0.94166 (16)0.36968 (9)0.10018 (7)0.0221 (5)
H7GA0.96850.39970.08710.027*
C8G1.14795 (16)0.35804 (9)0.07979 (6)0.0209 (5)
C9G1.08977 (17)0.26937 (8)0.05733 (6)0.0202 (5)
C10G1.01953 (16)0.21699 (8)0.04971 (7)0.0200 (4)
H10G0.99090.21240.07640.024*
C11G0.92961 (16)0.22226 (8)0.01104 (7)0.0202 (5)
C12G0.94703 (18)0.22974 (9)−0.03141 (7)0.0241 (5)
H12G1.01450.2316−0.03620.029*
C13G0.86454 (18)0.23437 (9)−0.06671 (7)0.0279 (5)
H13G0.87780.2394−0.09480.033*
C14G0.76256 (18)0.23168 (9)−0.06087 (7)0.0270 (5)
C15G0.74543 (18)0.22366 (9)−0.01858 (8)0.0284 (5)
H15G0.67780.2213−0.01390.034*
C16G0.82765 (17)0.21918 (8)0.01690 (7)0.0242 (5)
H16G0.81430.21410.04500.029*
C17G0.67432 (19)0.23786 (10)−0.09968 (8)0.0392 (6)
H17L0.62760.2644−0.09040.047*
H17M0.70270.2546−0.12300.047*
C18G0.6130 (3)0.18650 (13)−0.11869 (11)0.0737 (11)
H18G0.57270.1778−0.09620.088*
C19G0.5293 (2)0.19908 (13)−0.15886 (9)0.0615 (9)
H19V0.48310.1664−0.16750.092*
H19W0.56160.2084−0.18300.092*
H19X0.49100.2303−0.15110.092*
C20G0.6627 (2)0.13471 (10)−0.12500 (9)0.0512 (8)
H20V0.70500.1255−0.09740.077*
H20W0.70540.1392−0.14660.077*
H20X0.61090.1049−0.13530.077*
C21G1.08169 (17)0.16519 (9)0.04283 (7)0.0270 (5)
H21S1.13690.16270.06810.041*
H21T1.11020.16870.01670.041*
H21U1.03680.13180.03940.041*
Cl1H1.02420 (5)0.40189 (3)−0.045821 (19)0.03688 (15)
S1H0.43759 (5)0.37605 (2)0.041519 (18)0.02556 (13)
N1H0.38960 (14)0.47216 (7)0.08227 (6)0.0239 (4)
H1HB0.33660.45640.09000.029*
N2H0.41720 (14)0.52880 (7)0.09088 (6)0.0239 (4)
N3H0.52718 (13)0.48497 (7)0.05740 (5)0.0196 (4)
N4H0.61012 (13)0.48358 (7)0.03534 (5)0.0205 (4)
C1H0.79151 (17)0.47527 (9)−0.00335 (7)0.0235 (5)
H1HA0.76690.5113−0.00150.028*
C2H0.87734 (17)0.46685 (9)−0.02172 (7)0.0257 (5)
H2HA0.91070.4969−0.03230.031*
C3H0.91316 (17)0.41282 (9)−0.02425 (7)0.0244 (5)
C4H0.86412 (17)0.36714 (9)−0.00976 (7)0.0261 (5)
H4HA0.88830.3311−0.01230.031*
C5H0.77832 (17)0.37606 (9)0.00866 (7)0.0243 (5)
H5HA0.74470.34570.01870.029*
C6H0.74128 (16)0.43015 (8)0.01248 (6)0.0199 (4)
C7H0.65312 (16)0.43635 (9)0.03395 (6)0.0206 (5)
H7HA0.62780.40560.04680.025*
C8H0.45228 (16)0.44400 (8)0.06095 (6)0.0209 (5)
C9H0.50066 (16)0.53573 (8)0.07510 (6)0.0197 (4)
C10H0.56260 (16)0.59010 (8)0.07582 (7)0.0211 (5)
H10H0.58890.59040.04830.025*
C11H0.65567 (16)0.59353 (8)0.11423 (7)0.0194 (4)
C12H0.64300 (17)0.60276 (9)0.15775 (7)0.0241 (5)
H12H0.57670.60590.16350.029*
C13H0.72808 (17)0.60732 (8)0.19258 (7)0.0251 (5)
H13H0.71780.61330.22140.030*
C14H0.82834 (17)0.60317 (8)0.18542 (7)0.0218 (5)
C15H0.84039 (17)0.59375 (9)0.14183 (7)0.0236 (5)
H15H0.90670.59070.13610.028*
C16H0.75610 (16)0.58881 (8)0.10692 (7)0.0220 (5)
H16H0.76650.58230.07820.026*
C17H0.92053 (17)0.60769 (9)0.22347 (7)0.0268 (5)
H17N0.90060.62640.24890.032*
H17O0.97500.63110.21540.032*
C18H0.96387 (17)0.55080 (9)0.23681 (7)0.0255 (5)
H18H0.98320.53200.21090.031*
C19H1.06095 (19)0.55962 (10)0.27334 (7)0.0351 (6)
H19Y1.11210.58240.26310.053*
H19Z1.08820.52370.28090.053*
H1911.04360.57820.29900.053*
C20H0.88276 (19)0.51299 (9)0.25169 (8)0.0319 (6)
H20Y0.91060.47700.25830.048*
H20Z0.82220.50800.22840.048*
H21V0.86440.53020.27770.048*
C21H0.49287 (17)0.64007 (9)0.07671 (7)0.0266 (5)
H21W0.43610.63600.05170.040*
H21X0.53240.67450.07550.040*
H21Y0.46640.64100.10350.040*
Cl1I1.21296 (5)0.48789 (3)0.37854 (2)0.04423 (17)
S1I0.63155 (5)0.47533 (2)0.466598 (18)0.02747 (13)
N1I0.59003 (14)0.57092 (7)0.51038 (6)0.0244 (4)
H1IB0.53570.55590.51750.029*
N2I0.62130 (14)0.62674 (7)0.52048 (6)0.0247 (4)
N3I0.72941 (13)0.58167 (7)0.48649 (5)0.0201 (4)
N4I0.81187 (13)0.57847 (7)0.46423 (5)0.0213 (4)
C1I0.98724 (17)0.56479 (9)0.42320 (7)0.0248 (5)
H1IA0.96240.60090.42390.030*
C2I1.06996 (18)0.55470 (9)0.40310 (7)0.0268 (5)
H2IA1.10060.58350.39010.032*
C3I1.10663 (18)0.50063 (10)0.40270 (7)0.0282 (5)
C4I1.06109 (18)0.45684 (9)0.42097 (7)0.0284 (5)
H4IA1.08580.42080.41990.034*
C5I0.97828 (17)0.46743 (9)0.44087 (7)0.0254 (5)
H5IA0.94730.43820.45330.030*
C6I0.94023 (16)0.52160 (8)0.44255 (6)0.0207 (5)
C7I0.85423 (16)0.53067 (8)0.46493 (7)0.0214 (5)
H7IA0.82980.50160.47980.026*
C8I0.65090 (17)0.54208 (9)0.48856 (7)0.0226 (5)
C9I0.70565 (17)0.63272 (8)0.50505 (7)0.0216 (5)
C10I0.76918 (16)0.68664 (8)0.50607 (7)0.0212 (5)
H10I0.79680.68640.47880.025*
C11I0.86090 (16)0.69193 (8)0.54503 (7)0.0193 (4)
C12I0.84706 (18)0.70529 (9)0.58789 (7)0.0253 (5)
H12I0.78040.70900.59310.030*
C13I0.93140 (18)0.71319 (9)0.62292 (7)0.0268 (5)
H13I0.92020.72200.65120.032*
C14I1.03210 (17)0.70825 (8)0.61671 (7)0.0231 (5)
C15I1.04555 (18)0.69423 (9)0.57389 (7)0.0261 (5)
H15I1.11220.69040.56880.031*
C16I0.96180 (17)0.68593 (9)0.53876 (7)0.0239 (5)
H16I0.97300.67620.51060.029*
C17I1.12368 (18)0.71675 (9)0.65488 (7)0.0282 (5)
H17T1.10160.73590.67970.034*
H17U1.17600.74110.64620.034*
C18I1.17252 (18)0.66182 (9)0.67021 (7)0.0273 (5)
H18I1.19520.64300.64510.033*
C19I1.2675 (2)0.67446 (11)0.70738 (8)0.0379 (6)
H1921.29970.63990.71540.057*
H1931.24650.69200.73270.057*
H1941.31600.69940.69740.057*
C20I1.0944 (2)0.62250 (9)0.68511 (8)0.0346 (6)
H21Z1.12600.58790.69340.052*
H22A1.03570.61470.66130.052*
H22B1.07210.64000.71010.052*
C21I0.69959 (17)0.73684 (9)0.50584 (7)0.0252 (5)
H22C0.64430.73270.48020.038*
H22D0.73980.77120.50500.038*
H22E0.67110.73800.53220.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0357 (4)0.0464 (4)0.0350 (3)0.0158 (3)0.0155 (3)0.0025 (3)
S1A0.0278 (3)0.0259 (3)0.0285 (3)−0.0075 (2)0.0104 (2)−0.0070 (2)
N1A0.0207 (11)0.0243 (9)0.0258 (9)−0.0042 (8)0.0058 (8)−0.0031 (7)
N2A0.0250 (11)0.0230 (9)0.0242 (9)−0.0010 (8)0.0029 (8)−0.0034 (7)
N3A0.0186 (10)0.0210 (9)0.0207 (9)−0.0006 (7)0.0044 (7)−0.0012 (7)
N4A0.0197 (10)0.0246 (9)0.0191 (9)0.0000 (8)0.0043 (7)0.0000 (7)
C1A0.0269 (13)0.0203 (11)0.0214 (11)0.0039 (9)0.0027 (9)0.0008 (8)
C2A0.0243 (13)0.0263 (12)0.0281 (12)0.0038 (10)0.0047 (10)0.0040 (9)
C3A0.0274 (14)0.0336 (12)0.0178 (10)0.0086 (10)0.0053 (9)0.0022 (9)
C4A0.0360 (15)0.0237 (11)0.0197 (11)0.0100 (10)0.0024 (10)−0.0006 (9)
C5A0.0299 (14)0.0221 (11)0.0200 (10)0.0013 (9)0.0003 (9)0.0014 (8)
C6A0.0196 (12)0.0248 (11)0.0153 (10)0.0022 (9)0.0011 (8)0.0008 (8)
C7A0.0244 (13)0.0206 (11)0.0197 (10)−0.0005 (9)−0.0010 (9)0.0021 (8)
C8A0.0236 (13)0.0232 (11)0.0181 (10)−0.0027 (9)0.0047 (9)0.0014 (8)
C9A0.0226 (13)0.0200 (10)0.0205 (10)0.0029 (9)0.0022 (9)0.0008 (8)
C10A0.0252 (13)0.0211 (11)0.0204 (10)−0.0015 (9)0.0047 (9)−0.0012 (8)
C11A0.0251 (13)0.0153 (10)0.0239 (11)−0.0014 (9)0.0027 (9)−0.0038 (8)
C12A0.0230 (13)0.0238 (11)0.0270 (11)−0.0013 (9)0.0048 (10)−0.0033 (9)
C13A0.0348 (15)0.0229 (11)0.0248 (11)0.0006 (10)0.0046 (10)−0.0016 (9)
C14A0.0287 (14)0.0196 (11)0.0339 (13)0.0033 (10)−0.0019 (10)−0.0075 (9)
C15A0.0239 (14)0.0283 (12)0.0351 (13)0.0024 (10)0.0053 (10)−0.0067 (10)
C16A0.0318 (14)0.0219 (11)0.0249 (11)−0.0018 (10)0.0078 (10)−0.0041 (9)
C17A0.0360 (16)0.0351 (13)0.0356 (13)0.0107 (11)−0.0045 (11)−0.0034 (11)
C18A0.0392 (17)0.0420 (15)0.0381 (14)0.0069 (12)−0.0090 (12)−0.0080 (12)
C19A0.061 (2)0.072 (2)0.0506 (18)0.0190 (17)−0.0242 (16)−0.0159 (16)
C20A0.087 (3)0.0431 (18)0.076 (2)−0.0200 (17)−0.027 (2)−0.0015 (16)
C21A0.0308 (14)0.0229 (11)0.0323 (12)0.0032 (10)0.0000 (10)−0.0003 (9)
Cl1B0.0323 (4)0.0573 (4)0.0332 (3)0.0098 (3)0.0144 (3)0.0024 (3)
S1B0.0276 (3)0.0255 (3)0.0246 (3)−0.0095 (2)0.0070 (2)−0.0059 (2)
N1B0.0206 (11)0.0253 (9)0.0243 (9)−0.0070 (8)0.0048 (8)−0.0035 (7)
N2B0.0242 (11)0.0235 (9)0.0234 (9)−0.0033 (8)0.0010 (8)−0.0036 (7)
N3B0.0190 (10)0.0217 (9)0.0177 (8)−0.0033 (7)0.0022 (7)0.0000 (7)
N4B0.0184 (10)0.0257 (9)0.0177 (9)−0.0026 (8)0.0023 (7)0.0021 (7)
C1B0.0253 (13)0.0192 (10)0.0244 (11)0.0019 (9)0.0033 (9)0.0011 (8)
C2B0.0252 (13)0.0263 (12)0.0274 (11)0.0019 (10)0.0050 (10)0.0066 (9)
C3B0.0247 (13)0.0355 (13)0.0205 (11)0.0075 (10)0.0049 (9)0.0063 (9)
C4B0.0350 (15)0.0292 (12)0.0220 (11)0.0094 (10)0.0020 (10)−0.0030 (9)
C5B0.0289 (14)0.0219 (11)0.0250 (11)0.0006 (9)−0.0001 (10)0.0005 (9)
C6B0.0221 (12)0.0218 (11)0.0181 (10)0.0008 (9)0.0006 (9)0.0024 (8)
C7B0.0236 (13)0.0200 (10)0.0201 (10)−0.0020 (9)−0.0003 (9)0.0022 (8)
C8B0.0210 (12)0.0227 (11)0.0199 (10)−0.0041 (9)0.0016 (9)0.0036 (8)
C9B0.0207 (13)0.0230 (11)0.0181 (10)0.0006 (9)0.0016 (9)0.0007 (8)
C10B0.0223 (13)0.0201 (10)0.0238 (11)−0.0025 (9)0.0015 (9)−0.0009 (8)
C11B0.0235 (13)0.0168 (10)0.0222 (11)−0.0003 (9)0.0025 (9)−0.0037 (8)
C12B0.0212 (13)0.0237 (11)0.0270 (11)−0.0032 (9)0.0040 (9)−0.0023 (9)
C13B0.0335 (15)0.0209 (11)0.0230 (11)−0.0019 (10)0.0024 (10)0.0000 (9)
C14B0.0261 (14)0.0219 (11)0.0301 (12)0.0044 (9)0.0005 (10)−0.0085 (9)
C15B0.0229 (13)0.0342 (13)0.0319 (12)0.0001 (10)0.0054 (10)−0.0075 (10)
C16B0.0244 (13)0.0258 (11)0.0248 (11)−0.0040 (9)0.0052 (10)−0.0031 (9)
C17B0.0306 (15)0.0362 (14)0.0372 (14)0.0087 (11)−0.0009 (11)−0.0025 (11)
C18B0.031 (2)0.0341 (18)0.0262 (17)−0.0017 (14)0.0021 (14)0.0033 (13)
C19B0.029 (3)0.033 (2)0.049 (3)−0.003 (2)0.000 (2)−0.0151 (18)
C20B0.038 (3)0.068 (3)0.033 (2)0.017 (2)−0.005 (2)−0.0003 (19)
C21B0.0259 (13)0.0214 (11)0.0325 (12)0.0011 (9)−0.0010 (10)−0.0019 (9)
Cl1C0.0294 (4)0.0600 (4)0.0309 (3)0.0093 (3)0.0140 (3)0.0042 (3)
S1C0.0275 (3)0.0221 (3)0.0255 (3)−0.0078 (2)0.0071 (2)−0.0038 (2)
N1C0.0199 (10)0.0236 (9)0.0253 (9)−0.0060 (8)0.0048 (8)−0.0031 (7)
N2C0.0234 (11)0.0232 (9)0.0250 (9)−0.0023 (8)0.0028 (8)−0.0028 (7)
N3C0.0212 (10)0.0185 (9)0.0194 (9)−0.0032 (7)0.0037 (7)0.0000 (7)
N4C0.0163 (10)0.0232 (9)0.0209 (9)−0.0028 (7)0.0045 (7)0.0012 (7)
C1C0.0250 (13)0.0192 (10)0.0259 (11)0.0027 (9)0.0048 (9)−0.0001 (9)
C2C0.0224 (13)0.0265 (12)0.0297 (12)0.0010 (9)0.0049 (10)0.0054 (9)
C3C0.0232 (13)0.0375 (13)0.0189 (10)0.0081 (10)0.0046 (9)0.0070 (9)
C4C0.0332 (15)0.0294 (12)0.0205 (11)0.0099 (10)0.0033 (10)−0.0030 (9)
C5C0.0285 (14)0.0224 (11)0.0212 (11)0.0038 (9)−0.0009 (9)0.0005 (8)
C6C0.0214 (12)0.0236 (11)0.0155 (10)0.0029 (9)0.0025 (9)0.0023 (8)
C7C0.0226 (13)0.0193 (10)0.0194 (10)−0.0030 (9)−0.0003 (9)0.0015 (8)
C8C0.0210 (12)0.0220 (11)0.0199 (10)−0.0021 (9)0.0029 (9)0.0026 (8)
C9C0.0195 (12)0.0217 (11)0.0194 (10)0.0008 (9)0.0029 (9)0.0002 (8)
C10C0.0240 (13)0.0202 (10)0.0228 (11)−0.0024 (9)0.0056 (9)−0.0016 (8)
C11C0.0232 (13)0.0194 (10)0.0243 (11)−0.0006 (9)0.0046 (9)−0.0055 (8)
C12C0.0250 (13)0.0219 (11)0.0274 (11)−0.0054 (9)0.0032 (10)−0.0038 (9)
C13C0.0344 (15)0.0207 (11)0.0277 (12)−0.0005 (10)0.0006 (10)−0.0037 (9)
C14C0.0280 (14)0.0306 (12)0.0304 (12)0.0066 (10)0.0011 (10)−0.0120 (10)
C15C0.0215 (14)0.0480 (15)0.0313 (13)−0.0022 (11)0.0086 (10)−0.0098 (11)
C16C0.0271 (14)0.0376 (13)0.0238 (11)−0.0019 (10)0.0054 (10)−0.0048 (10)
C17C0.0301 (15)0.0505 (16)0.0327 (13)0.0126 (12)0.0007 (11)−0.0052 (11)
C18C0.0409 (17)0.0408 (15)0.0329 (13)0.0005 (12)−0.0017 (12)0.0015 (11)
C19C0.0377 (16)0.0370 (14)0.0304 (13)−0.0084 (11)0.0043 (11)−0.0032 (10)
C20C0.060 (2)0.0511 (18)0.0441 (16)0.0034 (15)−0.0195 (15)0.0040 (13)
C21C0.0242 (13)0.0227 (11)0.0339 (12)0.0010 (9)0.0041 (10)−0.0019 (9)
Cl1D0.0416 (4)0.0476 (4)0.0427 (4)0.0160 (3)0.0221 (3)−0.0010 (3)
S1D0.0286 (3)0.0255 (3)0.0324 (3)−0.0097 (2)0.0119 (3)−0.0102 (2)
N1D0.0212 (11)0.0228 (9)0.0285 (10)−0.0054 (8)0.0077 (8)−0.0048 (7)
N2D0.0216 (11)0.0221 (9)0.0266 (10)−0.0014 (8)0.0036 (8)−0.0038 (7)
N3D0.0192 (10)0.0184 (9)0.0200 (9)−0.0028 (7)0.0053 (7)−0.0017 (7)
N4D0.0176 (10)0.0238 (9)0.0188 (9)−0.0018 (7)0.0029 (7)−0.0018 (7)
C1D0.0246 (13)0.0213 (11)0.0237 (11)0.0030 (9)0.0040 (9)−0.0012 (8)
C2D0.0289 (14)0.0255 (12)0.0283 (12)0.0019 (10)0.0067 (10)0.0020 (9)
C3D0.0252 (13)0.0351 (13)0.0222 (11)0.0100 (10)0.0071 (9)−0.0028 (9)
C4D0.0372 (15)0.0242 (12)0.0253 (11)0.0115 (10)0.0034 (10)−0.0029 (9)
C5D0.0307 (14)0.0215 (11)0.0248 (11)0.0028 (10)0.0029 (10)−0.0019 (9)
C6D0.0218 (12)0.0235 (11)0.0176 (10)0.0016 (9)0.0003 (9)−0.0029 (8)
C7D0.0234 (13)0.0208 (11)0.0222 (11)−0.0021 (9)−0.0007 (9)−0.0018 (8)
C8D0.0215 (13)0.0214 (11)0.0226 (11)−0.0014 (9)0.0037 (9)0.0001 (8)
C9D0.0211 (13)0.0188 (10)0.0209 (10)0.0002 (9)0.0017 (9)−0.0009 (8)
C10D0.0248 (13)0.0199 (10)0.0203 (10)−0.0013 (9)0.0039 (9)−0.0009 (8)
C11D0.0208 (12)0.0165 (10)0.0237 (11)−0.0018 (9)0.0051 (9)−0.0043 (8)
C12D0.0212 (13)0.0281 (12)0.0243 (11)−0.0031 (9)0.0062 (9)−0.0017 (9)
C13D0.0299 (14)0.0274 (12)0.0195 (11)−0.0018 (10)0.0038 (10)0.0012 (9)
C14D0.0234 (13)0.0198 (11)0.0262 (11)0.0015 (9)0.0021 (9)−0.0022 (9)
C15D0.0196 (13)0.0255 (11)0.0312 (12)−0.0014 (9)0.0086 (10)−0.0030 (9)
C16D0.0267 (13)0.0223 (11)0.0213 (11)−0.0023 (9)0.0058 (9)−0.0007 (8)
C17D0.0289 (14)0.0312 (12)0.0300 (12)0.0047 (10)0.0019 (10)0.0008 (10)
C18D0.0345 (15)0.0368 (14)0.0350 (13)0.0036 (11)−0.0049 (11)−0.0042 (11)
C19D0.0443 (18)0.0543 (17)0.0391 (15)0.0077 (14)−0.0124 (13)−0.0045 (13)
C20D0.080 (2)0.0307 (15)0.064 (2)−0.0105 (15)−0.0362 (17)0.0045 (13)
C21D0.0261 (14)0.0229 (11)0.0335 (12)−0.0011 (9)0.0015 (10)−0.0037 (9)
Cl1E0.0261 (4)0.0951 (6)0.0372 (4)0.0076 (4)0.0134 (3)−0.0141 (4)
S1E0.0274 (3)0.0191 (3)0.0300 (3)−0.0041 (2)0.0109 (2)−0.0024 (2)
N1E0.0218 (11)0.0224 (9)0.0297 (10)−0.0046 (8)0.0083 (8)−0.0031 (8)
N2E0.0212 (11)0.0221 (9)0.0293 (10)−0.0024 (8)0.0067 (8)−0.0036 (7)
N3E0.0173 (10)0.0179 (9)0.0222 (9)−0.0011 (7)0.0045 (7)0.0008 (7)
N4E0.0167 (10)0.0234 (9)0.0222 (9)0.0004 (7)0.0063 (7)0.0010 (7)
C1E0.0237 (13)0.0261 (11)0.0269 (11)0.0051 (9)0.0048 (10)0.0039 (9)
C2E0.0265 (14)0.0397 (14)0.0273 (12)0.0024 (11)0.0064 (10)0.0069 (10)
C3E0.0192 (13)0.0550 (16)0.0208 (11)0.0088 (11)0.0043 (9)−0.0032 (10)
C4E0.0294 (15)0.0393 (14)0.0315 (13)0.0139 (11)0.0031 (11)−0.0109 (11)
C5E0.0275 (14)0.0250 (12)0.0298 (12)0.0063 (10)0.0014 (10)−0.0035 (9)
C6E0.0179 (12)0.0252 (11)0.0182 (10)0.0032 (9)0.0021 (9)−0.0004 (8)
C7E0.0227 (13)0.0187 (10)0.0228 (11)0.0006 (9)0.0028 (9)0.0016 (8)
C8E0.0205 (12)0.0229 (11)0.0206 (10)−0.0011 (9)0.0036 (9)0.0020 (8)
C9E0.0187 (12)0.0210 (10)0.0209 (10)0.0023 (9)0.0035 (9)−0.0003 (8)
C10E0.0202 (12)0.0170 (10)0.0249 (11)−0.0006 (9)0.0066 (9)−0.0008 (8)
C11E0.0199 (12)0.0128 (9)0.0256 (11)0.0017 (8)0.0060 (9)−0.0017 (8)
C12E0.0204 (13)0.0233 (11)0.0300 (12)0.0030 (9)0.0102 (10)0.0000 (9)
C13E0.0336 (14)0.0191 (11)0.0242 (11)0.0044 (9)0.0107 (10)0.0007 (8)
C14E0.0225 (13)0.0157 (10)0.0279 (11)−0.0004 (9)0.0043 (9)0.0004 (8)
C15E0.0187 (12)0.0231 (11)0.0314 (12)−0.0028 (9)0.0076 (10)0.0011 (9)
C16E0.0229 (13)0.0209 (11)0.0248 (11)−0.0020 (9)0.0079 (9)0.0022 (8)
C17E0.0293 (14)0.0259 (12)0.0289 (12)−0.0026 (10)0.0013 (10)−0.0001 (9)
C18E0.0260 (13)0.0329 (12)0.0221 (11)0.0055 (10)0.0071 (9)0.0002 (9)
C19E0.0312 (15)0.0457 (15)0.0341 (13)0.0092 (12)0.0015 (11)0.0032 (11)
C20E0.0371 (15)0.0266 (12)0.0289 (12)0.0047 (10)0.0097 (11)0.0020 (9)
C21E0.0230 (13)0.0223 (11)0.0343 (12)0.0033 (9)0.0050 (10)0.0015 (9)
Cl1F0.0291 (4)0.0704 (5)0.0380 (3)0.0105 (3)0.0165 (3)−0.0011 (3)
S1F0.0295 (3)0.0197 (3)0.0282 (3)−0.0033 (2)0.0103 (2)−0.0012 (2)
N1F0.0211 (11)0.0208 (9)0.0273 (10)−0.0040 (8)0.0071 (8)−0.0019 (7)
N2F0.0221 (11)0.0214 (9)0.0269 (9)−0.0015 (8)0.0044 (8)−0.0024 (7)
N3F0.0188 (10)0.0176 (8)0.0216 (9)−0.0004 (7)0.0060 (7)0.0008 (7)
N4F0.0182 (10)0.0237 (9)0.0199 (9)0.0012 (7)0.0058 (7)0.0007 (7)
C1F0.0219 (13)0.0223 (11)0.0245 (11)0.0056 (9)0.0035 (9)0.0013 (9)
C2F0.0238 (13)0.0293 (12)0.0262 (11)0.0015 (10)0.0050 (10)0.0059 (9)
C3F0.0221 (13)0.0424 (14)0.0191 (11)0.0089 (10)0.0058 (9)0.0032 (9)
C4F0.0320 (15)0.0331 (13)0.0208 (11)0.0131 (11)0.0016 (10)−0.0041 (9)
C5F0.0265 (13)0.0209 (11)0.0268 (11)0.0062 (9)0.0017 (10)−0.0005 (9)
C6F0.0192 (12)0.0223 (11)0.0194 (10)0.0033 (9)0.0027 (9)0.0024 (8)
C7F0.0201 (12)0.0195 (10)0.0220 (10)−0.0007 (9)0.0019 (9)0.0019 (8)
C8F0.0199 (12)0.0215 (11)0.0204 (10)0.0008 (9)0.0028 (9)0.0052 (8)
C9F0.0200 (12)0.0213 (11)0.0204 (10)0.0022 (9)0.0020 (9)0.0006 (8)
C10F0.0217 (12)0.0202 (10)0.0214 (10)0.0007 (9)0.0051 (9)0.0005 (8)
C11F0.0204 (12)0.0136 (10)0.0255 (11)0.0009 (8)0.0060 (9)−0.0006 (8)
C12F0.0196 (12)0.0253 (11)0.0278 (11)0.0033 (9)0.0097 (9)0.0000 (9)
C13F0.0287 (14)0.0236 (11)0.0229 (11)0.0033 (9)0.0106 (10)0.0010 (9)
C14F0.0233 (13)0.0174 (10)0.0246 (11)−0.0015 (9)0.0023 (9)−0.0008 (8)
C15F0.0168 (12)0.0243 (11)0.0307 (12)−0.0049 (9)0.0073 (9)0.0008 (9)
C16F0.0266 (13)0.0196 (10)0.0225 (11)−0.0037 (9)0.0090 (9)−0.0007 (8)
C17F0.0263 (14)0.0286 (12)0.0289 (12)−0.0046 (10)0.0022 (10)0.0008 (9)
C18F0.0247 (14)0.0399 (14)0.0240 (11)0.0057 (10)0.0062 (10)0.0011 (10)
C19F0.0321 (16)0.0569 (17)0.0358 (14)0.0064 (13)−0.0003 (12)0.0064 (12)
C20F0.0380 (16)0.0311 (13)0.0326 (13)0.0079 (11)0.0089 (11)0.0048 (10)
C21F0.0235 (13)0.0214 (11)0.0330 (12)0.0048 (9)0.0048 (10)0.0018 (9)
Cl1G0.0428 (4)0.0482 (4)0.0446 (4)0.0182 (3)0.0234 (3)0.0004 (3)
S1G0.0277 (3)0.0206 (3)0.0276 (3)−0.0052 (2)0.0100 (2)−0.0041 (2)
N1G0.0215 (11)0.0215 (9)0.0265 (9)−0.0042 (8)0.0061 (8)−0.0024 (7)
N2G0.0217 (11)0.0216 (9)0.0255 (9)−0.0007 (8)0.0048 (8)−0.0030 (7)
N3G0.0174 (10)0.0173 (8)0.0212 (9)0.0000 (7)0.0054 (7)−0.0003 (7)
N4G0.0174 (10)0.0232 (9)0.0201 (9)0.0007 (7)0.0038 (7)−0.0008 (7)
C1G0.0243 (13)0.0219 (11)0.0253 (11)0.0042 (9)0.0034 (9)0.0003 (9)
C2G0.0278 (14)0.0274 (12)0.0246 (11)0.0049 (10)0.0064 (10)0.0023 (9)
C3G0.0264 (14)0.0338 (13)0.0223 (11)0.0092 (10)0.0065 (10)−0.0038 (9)
C4G0.0354 (15)0.0238 (11)0.0255 (11)0.0115 (10)0.0018 (10)−0.0027 (9)
C5G0.0283 (14)0.0215 (11)0.0240 (11)0.0039 (9)0.0001 (10)−0.0001 (9)
C6G0.0193 (12)0.0231 (11)0.0194 (10)0.0037 (9)−0.0010 (9)−0.0031 (8)
C7G0.0222 (13)0.0206 (11)0.0216 (11)0.0000 (9)0.0007 (9)−0.0002 (8)
C8G0.0192 (12)0.0236 (11)0.0188 (10)−0.0012 (9)0.0016 (9)0.0007 (8)
C9G0.0203 (13)0.0210 (10)0.0185 (10)0.0017 (9)0.0020 (9)0.0001 (8)
C10G0.0196 (12)0.0174 (10)0.0232 (10)0.0005 (8)0.0051 (9)0.0004 (8)
C11G0.0201 (12)0.0142 (10)0.0257 (11)−0.0007 (8)0.0045 (9)−0.0023 (8)
C12G0.0230 (13)0.0247 (11)0.0254 (11)−0.0004 (9)0.0078 (9)−0.0017 (9)
C13G0.0328 (15)0.0270 (12)0.0232 (11)−0.0001 (10)0.0054 (10)−0.0020 (9)
C14G0.0265 (14)0.0173 (10)0.0340 (13)0.0008 (9)−0.0011 (10)−0.0009 (9)
C15G0.0190 (13)0.0254 (12)0.0407 (13)−0.0001 (9)0.0067 (10)−0.0017 (10)
C16G0.0237 (13)0.0228 (11)0.0275 (11)−0.0011 (9)0.0094 (10)−0.0001 (9)
C17G0.0332 (15)0.0323 (13)0.0448 (15)0.0038 (11)−0.0097 (12)0.0017 (11)
C18G0.084 (3)0.0505 (18)0.061 (2)0.0240 (17)−0.0443 (18)−0.0234 (15)
C19G0.063 (2)0.0565 (19)0.0480 (17)0.0131 (16)−0.0270 (15)−0.0160 (14)
C20G0.062 (2)0.0312 (14)0.0505 (17)−0.0050 (13)−0.0091 (15)−0.0001 (12)
C21G0.0243 (13)0.0200 (11)0.0348 (12)0.0023 (9)0.0019 (10)−0.0024 (9)
Cl1H0.0265 (3)0.0524 (4)0.0345 (3)0.0095 (3)0.0128 (3)−0.0033 (3)
S1H0.0278 (3)0.0208 (3)0.0297 (3)−0.0036 (2)0.0114 (2)−0.0023 (2)
N1H0.0217 (11)0.0224 (9)0.0290 (10)−0.0044 (8)0.0107 (8)−0.0020 (7)
N2H0.0221 (11)0.0211 (9)0.0286 (10)−0.0011 (8)0.0069 (8)−0.0032 (7)
N3H0.0170 (10)0.0205 (9)0.0224 (9)0.0015 (7)0.0063 (7)0.0013 (7)
N4H0.0178 (10)0.0231 (9)0.0210 (9)0.0013 (7)0.0054 (7)0.0001 (7)
C1H0.0224 (13)0.0229 (11)0.0247 (11)0.0036 (9)0.0026 (9)0.0026 (9)
C2H0.0229 (13)0.0285 (12)0.0261 (11)0.0014 (10)0.0049 (10)0.0058 (9)
C3H0.0188 (12)0.0364 (13)0.0175 (10)0.0076 (10)0.0021 (9)−0.0031 (9)
C4H0.0264 (14)0.0266 (12)0.0242 (11)0.0071 (10)0.0029 (10)−0.0039 (9)
C5H0.0238 (13)0.0224 (11)0.0255 (11)0.0010 (9)0.0027 (9)−0.0012 (9)
C6H0.0170 (12)0.0232 (11)0.0182 (10)0.0012 (9)0.0011 (8)−0.0008 (8)
C7H0.0177 (12)0.0219 (11)0.0216 (10)−0.0003 (9)0.0024 (9)0.0023 (8)
C8H0.0198 (12)0.0224 (11)0.0209 (10)0.0014 (9)0.0046 (9)0.0030 (8)
C9H0.0164 (12)0.0209 (10)0.0219 (10)0.0026 (9)0.0041 (9)0.0000 (8)
C10H0.0176 (12)0.0209 (10)0.0255 (11)0.0007 (9)0.0061 (9)0.0024 (8)
C11H0.0198 (12)0.0140 (10)0.0251 (11)0.0012 (8)0.0060 (9)0.0027 (8)
C12H0.0211 (13)0.0241 (11)0.0295 (12)0.0040 (9)0.0101 (10)0.0006 (9)
C13H0.0314 (14)0.0226 (11)0.0231 (11)0.0060 (10)0.0098 (10)−0.0012 (9)
C14H0.0216 (13)0.0146 (10)0.0289 (11)0.0008 (9)0.0045 (9)0.0010 (8)
C15H0.0164 (12)0.0256 (11)0.0306 (12)0.0009 (9)0.0092 (9)0.0031 (9)
C16H0.0222 (13)0.0224 (11)0.0235 (11)−0.0002 (9)0.0100 (9)0.0016 (8)
C17H0.0270 (14)0.0237 (11)0.0276 (12)−0.0025 (10)0.0023 (10)−0.0010 (9)
C18H0.0279 (14)0.0261 (11)0.0239 (11)0.0063 (10)0.0079 (10)0.0001 (9)
C19H0.0362 (16)0.0386 (14)0.0289 (12)0.0106 (11)0.0020 (11)−0.0023 (10)
C20H0.0391 (16)0.0269 (12)0.0331 (13)0.0069 (11)0.0136 (11)0.0057 (10)
C21H0.0207 (13)0.0234 (11)0.0362 (13)0.0030 (9)0.0067 (10)0.0015 (9)
Cl1I0.0440 (4)0.0502 (4)0.0469 (4)0.0210 (3)0.0258 (3)0.0029 (3)
S1I0.0290 (3)0.0224 (3)0.0327 (3)−0.0040 (2)0.0125 (3)−0.0031 (2)
N1I0.0218 (11)0.0218 (9)0.0309 (10)−0.0042 (8)0.0104 (8)−0.0017 (8)
N2I0.0229 (11)0.0220 (9)0.0299 (10)−0.0022 (8)0.0085 (8)−0.0026 (8)
N3I0.0181 (10)0.0199 (9)0.0231 (9)0.0004 (7)0.0060 (7)0.0008 (7)
N4I0.0192 (10)0.0228 (9)0.0228 (9)0.0014 (8)0.0072 (8)−0.0012 (7)
C1I0.0248 (13)0.0226 (11)0.0266 (11)0.0055 (9)0.0035 (10)−0.0004 (9)
C2I0.0282 (14)0.0275 (12)0.0265 (11)0.0064 (10)0.0081 (10)0.0040 (9)
C3I0.0278 (14)0.0347 (13)0.0233 (11)0.0100 (10)0.0075 (10)−0.0014 (9)
C4I0.0343 (15)0.0222 (11)0.0277 (12)0.0111 (10)0.0035 (10)−0.0032 (9)
C5I0.0278 (14)0.0220 (11)0.0250 (11)0.0035 (9)0.0022 (10)−0.0010 (9)
C6I0.0182 (12)0.0225 (11)0.0203 (10)0.0038 (9)0.0017 (9)−0.0022 (8)
C7I0.0198 (12)0.0199 (10)0.0227 (11)−0.0003 (9)0.0007 (9)0.0008 (8)
C8I0.0204 (13)0.0251 (11)0.0228 (11)0.0004 (9)0.0052 (9)0.0027 (9)
C9I0.0210 (13)0.0212 (11)0.0228 (11)0.0031 (9)0.0049 (9)0.0005 (8)
C10I0.0210 (12)0.0201 (10)0.0241 (11)0.0023 (9)0.0080 (9)0.0005 (8)
C11I0.0203 (12)0.0135 (9)0.0253 (11)0.0003 (8)0.0069 (9)0.0030 (8)
C12I0.0215 (13)0.0268 (11)0.0305 (12)0.0030 (9)0.0118 (10)0.0019 (9)
C13I0.0325 (14)0.0256 (11)0.0245 (11)0.0037 (10)0.0111 (10)−0.0017 (9)
C14I0.0261 (13)0.0150 (10)0.0292 (11)−0.0001 (9)0.0075 (10)0.0027 (8)
C15I0.0194 (13)0.0282 (12)0.0329 (12)0.0023 (9)0.0096 (10)0.0043 (9)
C16I0.0252 (13)0.0249 (11)0.0246 (11)0.0029 (9)0.0117 (9)0.0024 (9)
C17I0.0311 (14)0.0246 (11)0.0267 (12)−0.0029 (10)0.0019 (10)−0.0001 (9)
C18I0.0328 (14)0.0281 (12)0.0232 (11)0.0076 (10)0.0100 (10)0.0020 (9)
C19I0.0388 (16)0.0445 (15)0.0298 (13)0.0106 (12)0.0041 (11)0.0018 (11)
C20I0.0454 (17)0.0281 (12)0.0353 (13)0.0103 (11)0.0174 (12)0.0073 (10)
C21I0.0223 (13)0.0226 (11)0.0316 (12)0.0047 (9)0.0069 (10)0.0003 (9)
Geometric parameters (Å, º) top
Cl1A—C3A1.745 (2)C6E—C7E1.463 (3)
S1A—C8A1.689 (2)C7E—H7EA0.93
N1A—C8A1.333 (3)C9E—C10E1.499 (3)
N1A—N2A1.376 (2)C10E—C11E1.523 (3)
N1A—H1AB0.86C10E—C21E1.529 (3)
N2A—C9A1.297 (3)C10E—H10E0.98
N3A—C8A1.383 (3)C11E—C16E1.388 (3)
N3A—C9A1.386 (3)C11E—C12E1.398 (3)
N3A—N4A1.396 (2)C12E—C13E1.381 (3)
N4A—C7A1.280 (3)C12E—H12E0.93
C1A—C2A1.375 (3)C13E—C14E1.394 (3)
C1A—C6A1.401 (3)C13E—H13E0.93
C1A—H1AA0.93C14E—C15E1.394 (3)
C2A—C3A1.390 (3)C14E—C17E1.508 (3)
C2A—H2AA0.93C15E—C16E1.387 (3)
C3A—C4A1.381 (3)C15E—H15E0.93
C4A—C5A1.385 (3)C16E—H16E0.93
C4A—H4AA0.93C17E—C18E1.537 (3)
C5A—C6A1.399 (3)C17E—H17H0.97
C5A—H5AA0.93C17E—H17I0.97
C6A—C7A1.458 (3)C18E—C20E1.518 (3)
C7A—H7AA0.93C18E—C19E1.528 (3)
C9A—C10A1.503 (3)C18E—H18E0.98
C10A—C11A1.525 (3)C19E—H19P0.96
C10A—C21A1.532 (3)C19E—H19Q0.96
C10A—H10A0.98C19E—H19R0.96
C11A—C16A1.392 (3)C20E—H20P0.96
C11A—C12A1.399 (3)C20E—H20Q0.96
C12A—C13A1.384 (3)C20E—H20R0.96
C12A—H12A0.93C21E—H21M0.96
C13A—C14A1.389 (3)C21E—H21N0.96
C13A—H13A0.93C21E—H21O0.96
C14A—C15A1.393 (3)Cl1F—C3F1.737 (2)
C14A—C17A1.512 (3)S1F—C8F1.686 (2)
C15A—C16A1.382 (3)N1F—C8F1.335 (3)
C15A—H15A0.93N1F—N2F1.376 (2)
C16A—H16A0.93N1F—H1FB0.86
C17A—C18A1.508 (3)N2F—C9F1.294 (3)
C17A—H17A0.97N3F—C8F1.384 (3)
C17A—H17B0.97N3F—C9F1.388 (3)
C18A—C20A1.472 (4)N3F—N4F1.395 (2)
C18A—C19A1.538 (3)N4F—C7F1.281 (3)
C18A—H18A0.98C1F—C2F1.381 (3)
C19A—H19A0.96C1F—C6F1.397 (3)
C19A—H19B0.96C1F—H1FA0.93
C19A—H19C0.96C2F—C3F1.389 (3)
C20A—H20A0.96C2F—H2FA0.93
C20A—H20B0.96C3F—C4F1.384 (3)
C20A—H20C0.96C4F—C5F1.378 (3)
C21A—H21A0.96C4F—H4FA0.93
C21A—H21B0.96C5F—C6F1.394 (3)
C21A—H21C0.96C5F—H5FA0.93
Cl1B—C3B1.742 (2)C6F—C7F1.461 (3)
S1B—C8B1.684 (2)C7F—H7FA0.93
N1B—C8B1.338 (3)C9F—C10F1.501 (3)
N1B—N2B1.383 (2)C10F—C11F1.521 (3)
N1B—H1BB0.86C10F—C21F1.534 (3)
N2B—C9B1.293 (3)C10F—H10F0.98
N3B—C8B1.386 (3)C11F—C16F1.391 (3)
N3B—C9B1.387 (3)C11F—C12F1.392 (3)
N3B—N4B1.394 (2)C12F—C13F1.383 (3)
N4B—C7B1.283 (3)C12F—H12F0.93
C1B—C2B1.379 (3)C13F—C14F1.390 (3)
C1B—C6B1.395 (3)C13F—H13F0.93
C1B—H1BA0.93C14F—C15F1.397 (3)
C2B—C3B1.390 (3)C14F—C17F1.505 (3)
C2B—H2BA0.93C15F—C16F1.383 (3)
C3B—C4B1.379 (3)C15F—H15F0.93
C4B—C5B1.376 (3)C16F—H16F0.93
C4B—H4BA0.93C17F—C18F1.537 (3)
C5B—C6B1.399 (3)C17F—H17J0.97
C5B—H5BA0.93C17F—H17K0.97
C6B—C7B1.461 (3)C18F—C20F1.513 (3)
C7B—H7BA0.93C18F—C19F1.525 (3)
C9B—C10B1.500 (3)C18F—H18F0.98
C10B—C11B1.521 (3)C19F—H19S0.96
C10B—C21B1.528 (3)C19F—H19T0.96
C10B—H10B0.98C19F—H19U0.96
C11B—C16B1.387 (3)C20F—H20S0.96
C11B—C12B1.390 (3)C20F—H20T0.96
C12B—C13B1.387 (3)C20F—H20U0.96
C12B—H12B0.93C21F—H21P0.96
C13B—C14B1.388 (3)C21F—H21Q0.96
C13B—H13B0.93C21F—H21R0.96
C14B—C15B1.396 (3)Cl1G—C3G1.743 (2)
C14B—C17B1.504 (3)S1G—C8G1.684 (2)
C15B—C16B1.392 (3)N1G—C8G1.338 (3)
C15B—H15B0.93N1G—N2G1.375 (2)
C16B—H16B0.93N1G—H1GB0.86
C17B—C18B1.509 (4)N2G—C9G1.292 (3)
C17B—C18X1.532 (9)N3G—C8G1.387 (3)
C17B—H17C0.97N3G—C9G1.388 (2)
C17B—H17Q0.97N3G—N4G1.397 (2)
C17B—H17R0.96N4G—C7G1.284 (3)
C17B—H17S0.96C1G—C2G1.375 (3)
C18B—C19B1.499 (6)C1G—C6G1.402 (3)
C18B—C20B1.523 (5)C1G—H1GA0.93
C18B—H18B0.98C2G—C3G1.391 (3)
C19B—H19D0.96C2G—H2GA0.93
C19B—H19E0.96C3G—C4G1.380 (3)
C19B—H19F0.96C4G—C5G1.380 (3)
C20B—H20D0.96C4G—H4GA0.93
C20B—H20E0.96C5G—C6G1.400 (3)
C20B—H20F0.96C5G—H5GA0.93
C18X—C19X1.16 (2)C6G—C7G1.461 (3)
C18X—C20X1.591 (17)C7G—H7GA0.93
C18X—H18J0.98C9G—C10G1.502 (3)
C19X—H19G0.96C10G—C11G1.518 (3)
C19X—H19H0.96C10G—C21G1.535 (3)
C19X—H19I0.96C10G—H10G0.98
C20X—H20G0.96C11G—C16G1.391 (3)
C20X—H20H0.96C11G—C12G1.393 (3)
C20X—H20I0.96C12G—C13G1.389 (3)
C21B—H21D0.96C12G—H12G0.93
C21B—H21E0.96C13G—C14G1.391 (3)
C21B—H21F0.96C13G—H13G0.93
Cl1C—C3C1.742 (2)C14G—C15G1.389 (3)
S1C—C8C1.685 (2)C14G—C17G1.511 (3)
N1C—C8C1.338 (3)C15G—C16G1.389 (3)
N1C—N2C1.379 (2)C15G—H15G0.93
N1C—H1CB0.86C16G—H16G0.93
N2C—C9C1.295 (3)C17G—C18G1.466 (4)
N3C—C8C1.384 (3)C17G—H17L0.97
N3C—C9C1.386 (3)C17G—H17M0.97
N3C—N4C1.393 (2)C18G—C20G1.440 (4)
N4C—C7C1.278 (3)C18G—C19G1.536 (4)
C1C—C2C1.382 (3)C18G—H18G0.98
C1C—C6C1.399 (3)C19G—H19V0.96
C1C—H1CA0.93C19G—H19W0.96
C2C—C3C1.386 (3)C19G—H19X0.96
C2C—H2CA0.93C20G—H20V0.96
C3C—C4C1.382 (3)C20G—H20W0.96
C4C—C5C1.376 (3)C20G—H20X0.96
C4C—H4CA0.93C21G—H21S0.96
C5C—C6C1.394 (3)C21G—H21T0.96
C5C—H5CA0.93C21G—H21U0.96
C6C—C7C1.464 (3)Cl1H—C3H1.747 (2)
C7C—H7CA0.93S1H—C8H1.685 (2)
C9C—C10C1.498 (3)N1H—C8H1.334 (3)
C10C—C11C1.519 (3)N1H—N2H1.379 (2)
C10C—C21C1.530 (3)N1H—H1HB0.86
C10C—H10C0.98N2H—C9H1.297 (3)
C11C—C16C1.388 (3)N3H—C8H1.383 (3)
C11C—C12C1.393 (3)N3H—C9H1.386 (2)
C12C—C13C1.381 (3)N3H—N4H1.399 (2)
C12C—H12C0.93N4H—C7H1.280 (3)
C13C—C14C1.389 (3)C1H—C2H1.380 (3)
C13C—H13C0.93C1H—C6H1.398 (3)
C14C—C15C1.398 (3)C1H—H1HA0.93
C14C—C17C1.515 (3)C2H—C3H1.390 (3)
C15C—C16C1.387 (3)C2H—H2HA0.93
C15C—H15C0.93C3H—C4H1.380 (3)
C16C—H16C0.93C4H—C5H1.382 (3)
C17C—C18C1.522 (3)C4H—H4HA0.93
C17C—H17D0.97C5H—C6H1.401 (3)
C17C—H17E0.97C5H—H5HA0.93
C18C—C19C1.490 (3)C6H—C7H1.456 (3)
C18C—C20C1.540 (3)C7H—H7HA0.93
C18C—H18C0.98C9H—C10H1.498 (3)
C19C—H19J0.96C10H—C11H1.522 (3)
C19C—H19K0.96C10H—C21H1.533 (3)
C19C—H19L0.96C10H—H10H0.98
C20C—H20J0.96C11H—C12H1.394 (3)
C20C—H20K0.96C11H—C16H1.394 (3)
C20C—H20L0.96C12H—C13H1.386 (3)
C21C—H21G0.96C12H—H12H0.93
C21C—H21H0.96C13H—C14H1.389 (3)
C21C—H21I0.96C13H—H13H0.93
Cl1D—C3D1.744 (2)C14H—C15H1.394 (3)
S1D—C8D1.688 (2)C14H—C17H1.508 (3)
N1D—C8D1.331 (3)C15H—C16H1.381 (3)
N1D—N2D1.377 (2)C15H—H15H0.93
N1D—H1DB0.86C16H—H16H0.93
N2D—C9D1.294 (3)C17H—C18H1.532 (3)
N3D—C8D1.382 (3)C17H—H17N0.97
N3D—C9D1.388 (2)C17H—H17O0.97
N3D—N4D1.400 (2)C18H—C20H1.524 (3)
N4D—C7D1.280 (3)C18H—C19H1.527 (3)
C1D—C2D1.379 (3)C18H—H18H0.98
C1D—C6D1.398 (3)C19H—H19Y0.96
C1D—H1DA0.93C19H—H19Z0.96
C2D—C3D1.386 (3)C19H—H1910.96
C2D—H2DA0.93C20H—H20Y0.96
C3D—C4D1.382 (3)C20H—H20Z0.96
C4D—C5D1.379 (3)C20H—H21V0.96
C4D—H4DA0.93C21H—H21W0.96
C5D—C6D1.401 (3)C21H—H21X0.96
C5D—H5DA0.93C21H—H21Y0.96
C6D—C7D1.457 (3)Cl1I—C3I1.743 (2)
C7D—H7DA0.93S1I—C8I1.683 (2)
C9D—C10D1.499 (3)N1I—C8I1.334 (3)
C10D—C11D1.521 (3)N1I—N2I1.376 (2)
C10D—C21D1.526 (3)N1I—H1IB0.86
C10D—H10D0.98N2I—C9I1.299 (3)
C11D—C16D1.387 (3)N3I—C8I1.384 (3)
C11D—C12D1.392 (3)N3I—C9I1.390 (3)
C12D—C13D1.384 (3)N3I—N4I1.399 (2)
C12D—H12D0.93N4I—C7I1.285 (3)
C13D—C14D1.392 (3)C1I—C2I1.381 (3)
C13D—H13D0.93C1I—C6I1.398 (3)
C14D—C15D1.386 (3)C1I—H1IA0.93
C14D—C17D1.507 (3)C2I—C3I1.391 (3)
C15D—C16D1.388 (3)C2I—H2IA0.93
C15D—H15D0.93C3I—C4I1.381 (3)
C16D—H16D0.93C4I—C5I1.380 (3)
C17D—C18D1.508 (3)C4I—H4IA0.93
C17D—H17F0.97C5I—C6I1.403 (3)
C17D—H17G0.97C5I—H5IA0.93
C18D—C20D1.491 (3)C6I—C7I1.458 (3)
C18D—C19D1.530 (3)C7I—H7IA0.93
C18D—H18D0.98C9I—C10I1.499 (3)
C19D—H19M0.96C10I—C11I1.521 (3)
C19D—H19N0.96C10I—C21I1.533 (3)
C19D—H19O0.96C10I—H10I0.98
C20D—H20M0.96C11I—C16I1.393 (3)
C20D—H20N0.96C11I—C12I1.394 (3)
C20D—H20O0.96C12I—C13I1.386 (3)
C21D—H21J0.96C12I—H12I0.93
C21D—H21K0.96C13I—C14I1.387 (3)
C21D—H21L0.96C13I—H13I0.93
Cl1E—C3E1.742 (2)C14I—C15I1.394 (3)
S1E—C8E1.686 (2)C14I—C17I1.508 (3)
N1E—C8E1.339 (3)C15I—C16I1.384 (3)
N1E—N2E1.376 (2)C15I—H15I0.93
N1E—H1EB0.86C16I—H16I0.93
N2E—C9E1.292 (3)C17I—C18I1.533 (3)
N3E—C8E1.381 (3)C17I—H17T0.97
N3E—C9E1.388 (2)C17I—H17U0.97
N3E—N4E1.393 (2)C18I—C20I1.517 (3)
N4E—C7E1.281 (3)C18I—C19I1.528 (3)
C1E—C2E1.382 (3)C18I—H18I0.98
C1E—C6E1.393 (3)C19I—H1920.96
C1E—H1EA0.93C19I—H1930.96
C2E—C3E1.390 (3)C19I—H1940.96
C2E—H2EA0.93C20I—H21Z0.96
C3E—C4E1.373 (3)C20I—H22A0.96
C4E—C5E1.382 (3)C20I—H22B0.96
C4E—H4EA0.93C21I—H22C0.96
C5E—C6E1.397 (3)C21I—H22D0.96
C5E—H5EA0.93C21I—H22E0.96
C8A—N1A—N2A114.17 (18)C9E—C10E—C11E109.83 (16)
C8A—N1A—H1AB122.9C9E—C10E—C21E109.97 (18)
N2A—N1A—H1AB122.9C11E—C10E—C21E112.18 (16)
C9A—N2A—N1A104.14 (17)C9E—C10E—H10E108.3
C8A—N3A—C9A107.86 (17)C11E—C10E—H10E108.3
C8A—N3A—N4A130.26 (16)C21E—C10E—H10E108.3
C9A—N3A—N4A121.09 (17)C16E—C11E—C12E118.05 (19)
C7A—N4A—N3A115.75 (17)C16E—C11E—C10E121.86 (18)
C2A—C1A—C6A120.8 (2)C12E—C11E—C10E120.09 (19)
C2A—C1A—H1AA119.6C13E—C12E—C11E120.7 (2)
C6A—C1A—H1AA119.6C13E—C12E—H12E119.7
C1A—C2A—C3A119.0 (2)C11E—C12E—H12E119.7
C1A—C2A—H2AA120.5C12E—C13E—C14E121.6 (2)
C3A—C2A—H2AA120.5C12E—C13E—H13E119.2
C4A—C3A—C2A121.9 (2)C14E—C13E—H13E119.2
C4A—C3A—Cl1A119.05 (17)C13E—C14E—C15E117.4 (2)
C2A—C3A—Cl1A119.06 (18)C13E—C14E—C17E120.9 (2)
C3A—C4A—C5A118.5 (2)C15E—C14E—C17E121.7 (2)
C3A—C4A—H4AA120.7C16E—C15E—C14E121.2 (2)
C5A—C4A—H4AA120.7C16E—C15E—H15E119.4
C4A—C5A—C6A121.1 (2)C14E—C15E—H15E119.4
C4A—C5A—H5AA119.4C15E—C16E—C11E121.0 (2)
C6A—C5A—H5AA119.4C15E—C16E—H16E119.5
C5A—C6A—C1A118.6 (2)C11E—C16E—H16E119.5
C5A—C6A—C7A118.84 (19)C14E—C17E—C18E114.69 (17)
C1A—C6A—C7A122.52 (19)C14E—C17E—H17H108.6
N4A—C7A—C6A120.83 (19)C18E—C17E—H17H108.6
N4A—C7A—H7AA119.6C14E—C17E—H17I108.6
C6A—C7A—H7AA119.6C18E—C17E—H17I108.6
N1A—C8A—N3A102.95 (17)H17H—C17E—H17I107.6
N1A—C8A—S1A127.91 (16)C20E—C18E—C19E110.29 (19)
N3A—C8A—S1A129.03 (16)C20E—C18E—C17E111.94 (19)
N2A—C9A—N3A110.79 (18)C19E—C18E—C17E109.42 (18)
N2A—C9A—C10A126.12 (19)C20E—C18E—H18E108.4
N3A—C9A—C10A123.07 (19)C19E—C18E—H18E108.4
C9A—C10A—C11A112.02 (17)C17E—C18E—H18E108.4
C9A—C10A—C21A110.50 (18)C18E—C19E—H19P109.5
C11A—C10A—C21A111.09 (16)C18E—C19E—H19Q109.5
C9A—C10A—H10A107.7H19P—C19E—H19Q109.5
C11A—C10A—H10A107.7C18E—C19E—H19R109.5
C21A—C10A—H10A107.7H19P—C19E—H19R109.5
C16A—C11A—C12A118.2 (2)H19Q—C19E—H19R109.5
C16A—C11A—C10A120.83 (19)C18E—C20E—H20P109.5
C12A—C11A—C10A120.9 (2)C18E—C20E—H20Q109.5
C13A—C12A—C11A120.2 (2)H20P—C20E—H20Q109.5
C13A—C12A—H12A119.9C18E—C20E—H20R109.5
C11A—C12A—H12A119.9H20P—C20E—H20R109.5
C12A—C13A—C14A121.7 (2)H20Q—C20E—H20R109.5
C12A—C13A—H13A119.1C10E—C21E—H21M109.5
C14A—C13A—H13A119.1C10E—C21E—H21N109.5
C13A—C14A—C15A117.6 (2)H21M—C21E—H21N109.5
C13A—C14A—C17A120.9 (2)C10E—C21E—H21O109.5
C15A—C14A—C17A121.5 (2)H21M—C21E—H21O109.5
C16A—C15A—C14A121.3 (2)H21N—C21E—H21O109.5
C16A—C15A—H15A119.4C8F—N1F—N2F114.33 (17)
C14A—C15A—H15A119.4C8F—N1F—H1FB122.8
C15A—C16A—C11A120.9 (2)N2F—N1F—H1FB122.8
C15A—C16A—H16A119.5C9F—N2F—N1F104.13 (17)
C11A—C16A—H16A119.5C8F—N3F—C9F107.97 (17)
C18A—C17A—C14A114.17 (19)C8F—N3F—N4F132.49 (16)
C18A—C17A—H17A108.7C9F—N3F—N4F119.16 (16)
C14A—C17A—H17A108.7C7F—N4F—N3F117.26 (17)
C18A—C17A—H17B108.7C2F—C1F—C6F120.9 (2)
C14A—C17A—H17B108.7C2F—C1F—H1FA119.5
H17A—C17A—H17B107.6C6F—C1F—H1FA119.5
C20A—C18A—C17A115.0 (2)C1F—C2F—C3F118.9 (2)
C20A—C18A—C19A110.7 (2)C1F—C2F—H2FA120.5
C17A—C18A—C19A110.4 (2)C3F—C2F—H2FA120.5
C20A—C18A—H18A106.7C4F—C3F—C2F121.4 (2)
C17A—C18A—H18A106.7C4F—C3F—Cl1F119.17 (18)
C19A—C18A—H18A106.7C2F—C3F—Cl1F119.44 (18)
C18A—C19A—H19A109.5C5F—C4F—C3F118.9 (2)
C18A—C19A—H19B109.5C5F—C4F—H4FA120.5
H19A—C19A—H19B109.5C3F—C4F—H4FA120.5
C18A—C19A—H19C109.5C4F—C5F—C6F121.3 (2)
H19A—C19A—H19C109.5C4F—C5F—H5FA119.4
H19B—C19A—H19C109.5C6F—C5F—H5FA119.4
C18A—C20A—H20A109.5C5F—C6F—C1F118.6 (2)
C18A—C20A—H20B109.5C5F—C6F—C7F118.79 (19)
H20A—C20A—H20B109.5C1F—C6F—C7F122.60 (19)
C18A—C20A—H20C109.5N4F—C7F—C6F119.14 (19)
H20A—C20A—H20C109.5N4F—C7F—H7FA120.4
H20B—C20A—H20C109.5C6F—C7F—H7FA120.4
C10A—C21A—H21A109.5N1F—C8F—N3F102.68 (17)
C10A—C21A—H21B109.5N1F—C8F—S1F126.67 (16)
H21A—C21A—H21B109.5N3F—C8F—S1F130.59 (16)
C10A—C21A—H21C109.5N2F—C9F—N3F110.81 (18)
H21A—C21A—H21C109.5N2F—C9F—C10F125.90 (19)
H21B—C21A—H21C109.5N3F—C9F—C10F123.29 (19)
C8B—N1B—N2B114.07 (17)C9F—C10F—C11F111.67 (16)
C8B—N1B—H1BB123.0C9F—C10F—C21F109.44 (18)
N2B—N1B—H1BB123.0C11F—C10F—C21F111.37 (16)
C9B—N2B—N1B104.32 (17)C9F—C10F—H10F108.1
C8B—N3B—C9B108.34 (17)C11F—C10F—H10F108.1
C8B—N3B—N4B132.47 (17)C21F—C10F—H10F108.1
C9B—N3B—N4B118.85 (16)C16F—C11F—C12F118.24 (19)
C7B—N4B—N3B118.20 (17)C16F—C11F—C10F121.56 (18)
C2B—C1B—C6B120.9 (2)C12F—C11F—C10F120.14 (19)
C2B—C1B—H1BA119.6C13F—C12F—C11F120.6 (2)
C6B—C1B—H1BA119.6C13F—C12F—H12F119.7
C1B—C2B—C3B119.1 (2)C11F—C12F—H12F119.7
C1B—C2B—H2BA120.4C12F—C13F—C14F121.7 (2)
C3B—C2B—H2BA120.4C12F—C13F—H13F119.2
C4B—C3B—C2B121.1 (2)C14F—C13F—H13F119.2
C4B—C3B—Cl1B119.35 (18)C13F—C14F—C15F117.27 (19)
C2B—C3B—Cl1B119.54 (18)C13F—C14F—C17F120.96 (19)
C5B—C4B—C3B119.5 (2)C15F—C14F—C17F121.8 (2)
C5B—C4B—H4BA120.3C16F—C15F—C14F121.4 (2)
C3B—C4B—H4BA120.3C16F—C15F—H15F119.3
C4B—C5B—C6B120.8 (2)C14F—C15F—H15F119.3
C4B—C5B—H5BA119.6C15F—C16F—C11F120.7 (2)
C6B—C5B—H5BA119.6C15F—C16F—H16F119.6
C1B—C6B—C5B118.6 (2)C11F—C16F—H16F119.6
C1B—C6B—C7B122.04 (19)C14F—C17F—C18F114.48 (18)
C5B—C6B—C7B119.28 (19)C14F—C17F—H17J108.6
N4B—C7B—C6B118.94 (19)C18F—C17F—H17J108.6
N4B—C7B—H7BA120.5C14F—C17F—H17K108.6
C6B—C7B—H7BA120.5C18F—C17F—H17K108.6
N1B—C8B—N3B102.51 (17)H17J—C17F—H17K107.6
N1B—C8B—S1B127.01 (16)C20F—C18F—C19F110.59 (19)
N3B—C8B—S1B130.43 (17)C20F—C18F—C17F111.55 (19)
N2B—C9B—N3B110.67 (18)C19F—C18F—C17F110.11 (19)
N2B—C9B—C10B125.86 (19)C20F—C18F—H18F108.2
N3B—C9B—C10B123.46 (19)C19F—C18F—H18F108.2
C9B—C10B—C11B110.61 (17)C17F—C18F—H18F108.2
C9B—C10B—C21B110.03 (18)C18F—C19F—H19S109.5
C11B—C10B—C21B111.56 (17)C18F—C19F—H19T109.5
C9B—C10B—H10B108.2H19S—C19F—H19T109.5
C11B—C10B—H10B108.2C18F—C19F—H19U109.5
C21B—C10B—H10B108.2H19S—C19F—H19U109.5
C16B—C11B—C12B118.2 (2)H19T—C19F—H19U109.5
C16B—C11B—C10B121.04 (19)C18F—C20F—H20S109.5
C12B—C11B—C10B120.7 (2)C18F—C20F—H20T109.5
C13B—C12B—C11B120.8 (2)H20S—C20F—H20T109.5
C13B—C12B—H12B119.6C18F—C20F—H20U109.5
C11B—C12B—H12B119.6H20S—C20F—H20U109.5
C12B—C13B—C14B121.3 (2)H20T—C20F—H20U109.5
C12B—C13B—H13B119.3C10F—C21F—H21P109.5
C14B—C13B—H13B119.3C10F—C21F—H21Q109.5
C13B—C14B—C15B118.0 (2)H21P—C21F—H21Q109.5
C13B—C14B—C17B120.5 (2)C10F—C21F—H21R109.5
C15B—C14B—C17B121.5 (2)H21P—C21F—H21R109.5
C16B—C15B—C14B120.6 (2)H21Q—C21F—H21R109.5
C16B—C15B—H15B119.7C8G—N1G—N2G114.40 (17)
C14B—C15B—H15B119.7C8G—N1G—H1GB122.8
C11B—C16B—C15B121.2 (2)N2G—N1G—H1GB122.8
C11B—C16B—H16B119.4C9G—N2G—N1G104.05 (17)
C15B—C16B—H16B119.4C8G—N3G—C9G107.77 (17)
C14B—C17B—C18B113.5 (2)C8G—N3G—N4G129.69 (16)
C14B—C17B—C18X116.7 (4)C9G—N3G—N4G121.51 (16)
C14B—C17B—H17C108.9C7G—N4G—N3G115.11 (17)
C18B—C17B—H17C108.9C2G—C1G—C6G120.5 (2)
C18X—C17B—H17C130.9C2G—C1G—H1GA119.7
C14B—C17B—H17Q108.9C6G—C1G—H1GA119.7
C18B—C17B—H17Q108.9C1G—C2G—C3G119.2 (2)
C18X—C17B—H17Q74.6C1G—C2G—H2GA120.4
H17C—C17B—H17Q107.7C3G—C2G—H2GA120.4
C14B—C17B—H17R108.2C4G—C3G—C2G121.6 (2)
C18X—C17B—H17R107.2C4G—C3G—Cl1G119.35 (17)
H17Q—C17B—H17R136.7C2G—C3G—Cl1G119.04 (18)
C14B—C17B—H17S108.0C5G—C4G—C3G118.8 (2)
C18B—C17B—H17S135.2C5G—C4G—H4GA120.6
C18X—C17B—H17S109.0C3G—C4G—H4GA120.6
H17C—C17B—H17S71.3C4G—C5G—C6G121.1 (2)
H17R—C17B—H17S107.3C4G—C5G—H5GA119.4
C19B—C18B—C17B117.3 (3)C6G—C5G—H5GA119.4
C19B—C18B—C20B111.4 (4)C5G—C6G—C1G118.7 (2)
C17B—C18B—C20B111.3 (3)C5G—C6G—C7G118.67 (19)
C19B—C18B—H17R145.3C1G—C6G—C7G122.63 (19)
C20B—C18B—H17R101.8N4G—C7G—C6G120.40 (19)
C19B—C18B—H18B105.2N4G—C7G—H7GA119.8
C17B—C18B—H18B105.2C6G—C7G—H7GA119.8
C20B—C18B—H18B105.2N1G—C8G—N3G102.59 (17)
H17R—C18B—H18B74.4N1G—C8G—S1G127.49 (16)
C19X—C18X—C17B122.8 (13)N3G—C8G—S1G129.83 (16)
C19X—C18X—C20X120.4 (14)N2G—C9G—N3G111.14 (18)
C17B—C18X—C20X109.0 (8)N2G—C9G—C10G125.57 (18)
C19X—C18X—H18J99.4N3G—C9G—C10G123.28 (19)
C17B—C18X—H18J99.4C9G—C10G—C11G111.04 (16)
C20X—C18X—H18J99.4C9G—C10G—C21G110.10 (17)
C18X—C19X—H19G109.5C11G—C10G—C21G111.67 (16)
C18X—C19X—H19H109.5C9G—C10G—H10G108.0
H19G—C19X—H19H109.5C11G—C10G—H10G108.0
C18X—C19X—H19I109.5C21G—C10G—H10G108.0
H19G—C19X—H19I109.5C16G—C11G—C12G118.2 (2)
H19H—C19X—H19I109.5C16G—C11G—C10G120.99 (19)
C18X—C20X—H20G109.5C12G—C11G—C10G120.83 (19)
C18X—C20X—H20H109.5C13G—C12G—C11G120.6 (2)
H20G—C20X—H20H109.5C13G—C12G—H12G119.7
C18X—C20X—H20I109.5C11G—C12G—H12G119.7
H20G—C20X—H20I109.5C12G—C13G—C14G121.3 (2)
H20H—C20X—H20I109.5C12G—C13G—H13G119.4
C10B—C21B—H21D109.5C14G—C13G—H13G119.4
C10B—C21B—H21E109.5C15G—C14G—C13G117.9 (2)
H21D—C21B—H21E109.5C15G—C14G—C17G121.9 (2)
C10B—C21B—H21F109.5C13G—C14G—C17G120.2 (2)
H21D—C21B—H21F109.5C14G—C15G—C16G121.1 (2)
H21E—C21B—H21F109.5C14G—C15G—H15G119.5
C8C—N1C—N2C114.32 (17)C16G—C15G—H15G119.5
C8C—N1C—H1CB122.8C15G—C16G—C11G120.9 (2)
N2C—N1C—H1CB122.8C15G—C16G—H16G119.5
C9C—N2C—N1C103.96 (17)C11G—C16G—H16G119.5
C8C—N3C—C9C108.14 (17)C18G—C17G—C14G117.2 (2)
C8C—N3C—N4C132.89 (17)C18G—C17G—H17L108.0
C9C—N3C—N4C118.64 (16)C14G—C17G—H17L108.0
C7C—N4C—N3C118.28 (17)C18G—C17G—H17M108.0
C2C—C1C—C6C120.6 (2)C14G—C17G—H17M108.0
C2C—C1C—H1CA119.7H17L—C17G—H17M107.2
C6C—C1C—H1CA119.7C20G—C18G—C17G120.7 (3)
C1C—C2C—C3C119.1 (2)C20G—C18G—C19G113.0 (2)
C1C—C2C—H2CA120.4C17G—C18G—C19G111.2 (2)
C3C—C2C—H2CA120.4C20G—C18G—H18G103.1
C4C—C3C—C2C121.3 (2)C17G—C18G—H18G103.1
C4C—C3C—Cl1C119.15 (18)C19G—C18G—H18G103.1
C2C—C3C—Cl1C119.52 (18)C18G—C19G—H19V109.5
C5C—C4C—C3C119.2 (2)C18G—C19G—H19W109.5
C5C—C4C—H4CA120.4H19V—C19G—H19W109.5
C3C—C4C—H4CA120.4C18G—C19G—H19X109.5
C4C—C5C—C6C121.0 (2)H19V—C19G—H19X109.5
C4C—C5C—H5CA119.5H19W—C19G—H19X109.5
C6C—C5C—H5CA119.5C18G—C20G—H20V109.5
C5C—C6C—C1C118.8 (2)C18G—C20G—H20W109.5
C5C—C6C—C7C119.64 (19)H20V—C20G—H20W109.5
C1C—C6C—C7C121.57 (19)C18G—C20G—H20X109.5
N4C—C7C—C6C118.86 (19)H20V—C20G—H20X109.5
N4C—C7C—H7CA120.6H20W—C20G—H20X109.5
C6C—C7C—H7CA120.6C10G—C21G—H21S109.5
N1C—C8C—N3C102.54 (17)C10G—C21G—H21T109.5
N1C—C8C—S1C126.85 (16)H21S—C21G—H21T109.5
N3C—C8C—S1C130.57 (16)C10G—C21G—H21U109.5
N2C—C9C—N3C110.95 (18)H21S—C21G—H21U109.5
N2C—C9C—C10C125.71 (19)H21T—C21G—H21U109.5
N3C—C9C—C10C123.32 (19)C8H—N1H—N2H114.15 (17)
C9C—C10C—C11C110.89 (17)C8H—N1H—H1HB122.9
C9C—C10C—C21C109.96 (18)N2H—N1H—H1HB122.9
C11C—C10C—C21C111.27 (17)C9H—N2H—N1H104.22 (16)
C9C—C10C—H10C108.2C8H—N3H—C9H108.30 (17)
C11C—C10C—H10C108.2C8H—N3H—N4H131.08 (16)
C21C—C10C—H10C108.2C9H—N3H—N4H120.06 (16)
C16C—C11C—C12C118.2 (2)C7H—N4H—N3H115.93 (17)
C16C—C11C—C10C121.25 (19)C2H—C1H—C6H120.5 (2)
C12C—C11C—C10C120.5 (2)C2H—C1H—H1HA119.7
C13C—C12C—C11C120.8 (2)C6H—C1H—H1HA119.7
C13C—C12C—H12C119.6C1H—C2H—C3H119.0 (2)
C11C—C12C—H12C119.6C1H—C2H—H2HA120.5
C12C—C13C—C14C121.5 (2)C3H—C2H—H2HA120.5
C12C—C13C—H13C119.3C4H—C3H—C2H121.9 (2)
C14C—C13C—H13C119.3C4H—C3H—Cl1H118.53 (17)
C13C—C14C—C15C117.6 (2)C2H—C3H—Cl1H119.54 (18)
C13C—C14C—C17C121.1 (2)C3H—C4H—C5H118.6 (2)
C15C—C14C—C17C121.3 (2)C3H—C4H—H4HA120.7
C16C—C15C—C14C121.1 (2)C5H—C4H—H4HA120.7
C16C—C15C—H15C119.5C4H—C5H—C6H121.0 (2)
C14C—C15C—H15C119.5C4H—C5H—H5HA119.5
C15C—C16C—C11C120.9 (2)C6H—C5H—H5HA119.5
C15C—C16C—H16C119.6C1H—C6H—C5H118.9 (2)
C11C—C16C—H16C119.6C1H—C6H—C7H123.45 (19)
C14C—C17C—C18C113.1 (2)C5H—C6H—C7H117.59 (19)
C14C—C17C—H17D109.0N4H—C7H—C6H120.79 (19)
C18C—C17C—H17D109.0N4H—C7H—H7HA119.6
C14C—C17C—H17E109.0C6H—C7H—H7HA119.6
C18C—C17C—H17E109.0N1H—C8H—N3H102.69 (17)
H17D—C17C—H17E107.8N1H—C8H—S1H127.36 (16)
C19C—C18C—C17C113.4 (2)N3H—C8H—S1H129.88 (16)
C19C—C18C—C20C111.2 (2)N2H—C9H—N3H110.54 (18)
C17C—C18C—C20C109.5 (2)N2H—C9H—C10H126.10 (18)
C19C—C18C—H18C107.5N3H—C9H—C10H123.35 (18)
C17C—C18C—H18C107.5C9H—C10H—C11H110.34 (16)
C20C—C18C—H18C107.5C9H—C10H—C21H110.16 (17)
C18C—C19C—H19J109.5C11H—C10H—C21H112.99 (17)
C18C—C19C—H19K109.5C9H—C10H—H10H107.7
H19J—C19C—H19K109.5C11H—C10H—H10H107.7
C18C—C19C—H19L109.5C21H—C10H—H10H107.7
H19J—C19C—H19L109.5C12H—C11H—C16H118.03 (19)
H19K—C19C—H19L109.5C12H—C11H—C10H120.81 (19)
C18C—C20C—H20J109.5C16H—C11H—C10H121.15 (18)
C18C—C20C—H20K109.5C13H—C12H—C11H120.7 (2)
H20J—C20C—H20K109.5C13H—C12H—H12H119.6
C18C—C20C—H20L109.5C11H—C12H—H12H119.6
H20J—C20C—H20L109.5C12H—C13H—C14H121.5 (2)
H20K—C20C—H20L109.5C12H—C13H—H13H119.3
C10C—C21C—H21G109.5C14H—C13H—H13H119.3
C10C—C21C—H21H109.5C13H—C14H—C15H117.5 (2)
H21G—C21C—H21H109.5C13H—C14H—C17H121.22 (19)
C10C—C21C—H21I109.5C15H—C14H—C17H121.3 (2)
H21G—C21C—H21I109.5C16H—C15H—C14H121.5 (2)
H21H—C21C—H21I109.5C16H—C15H—H15H119.3
C8D—N1D—N2D113.98 (17)C14H—C15H—H15H119.3
C8D—N1D—H1DB123.0C15H—C16H—C11H120.80 (19)
N2D—N1D—H1DB123.0C15H—C16H—H16H119.6
C9D—N2D—N1D104.35 (17)C11H—C16H—H16H119.6
C8D—N3D—C9D107.92 (17)C14H—C17H—C18H113.95 (17)
C8D—N3D—N4D130.32 (16)C14H—C17H—H17N108.8
C9D—N3D—N4D120.82 (16)C18H—C17H—H17N108.8
C7D—N4D—N3D115.62 (17)C14H—C17H—H17O108.8
C2D—C1D—C6D120.5 (2)C18H—C17H—H17O108.8
C2D—C1D—H1DA119.7H17N—C17H—H17O107.7
C6D—C1D—H1DA119.7C20H—C18H—C19H110.51 (19)
C1D—C2D—C3D119.2 (2)C20H—C18H—C17H111.16 (19)
C1D—C2D—H2DA120.4C19H—C18H—C17H110.33 (18)
C3D—C2D—H2DA120.4C20H—C18H—H18H108.2
C4D—C3D—C2D121.7 (2)C19H—C18H—H18H108.2
C4D—C3D—Cl1D119.10 (17)C17H—C18H—H18H108.2
C2D—C3D—Cl1D119.18 (18)C18H—C19H—H19Y109.5
C5D—C4D—C3D118.8 (2)C18H—C19H—H19Z109.5
C5D—C4D—H4DA120.6H19Y—C19H—H19Z109.5
C3D—C4D—H4DA120.6C18H—C19H—H191109.5
C4D—C5D—C6D121.0 (2)H19Y—C19H—H191109.5
C4D—C5D—H5DA119.5H19Z—C19H—H191109.5
C6D—C5D—H5DA119.5C18H—C20H—H20Y109.5
C1D—C6D—C5D118.8 (2)C18H—C20H—H20Z109.5
C1D—C6D—C7D122.42 (19)H20Y—C20H—H20Z109.5
C5D—C6D—C7D118.81 (19)C18H—C20H—H21V109.5
N4D—C7D—C6D120.3 (2)H20Y—C20H—H21V109.5
N4D—C7D—H7DA119.9H20Z—C20H—H21V109.5
C6D—C7D—H7DA119.9C10H—C21H—H21W109.5
N1D—C8D—N3D103.06 (17)C10H—C21H—H21X109.5
N1D—C8D—S1D127.89 (17)H21W—C21H—H21X109.5
N3D—C8D—S1D128.94 (16)C10H—C21H—H21Y109.5
N2D—C9D—N3D110.60 (18)H21W—C21H—H21Y109.5
N2D—C9D—C10D126.23 (19)H21X—C21H—H21Y109.5
N3D—C9D—C10D123.16 (19)C8I—N1I—N2I114.45 (18)
C9D—C10D—C11D111.68 (17)C8I—N1I—H1IB122.8
C9D—C10D—C21D110.64 (18)N2I—N1I—H1IB122.8
C11D—C10D—C21D111.45 (16)C9I—N2I—N1I104.16 (17)
C9D—C10D—H10D107.6C8I—N3I—C9I108.13 (17)
C11D—C10D—H10D107.6C8I—N3I—N4I130.08 (16)
C21D—C10D—H10D107.6C9I—N3I—N4I121.03 (16)
C16D—C11D—C12D118.1 (2)C7I—N4I—N3I115.07 (17)
C16D—C11D—C10D120.92 (18)C2I—C1I—C6I120.9 (2)
C12D—C11D—C10D120.90 (19)C2I—C1I—H1IA119.5
C13D—C12D—C11D120.6 (2)C6I—C1I—H1IA119.5
C13D—C12D—H12D119.7C1I—C2I—C3I118.8 (2)
C11D—C12D—H12D119.7C1I—C2I—H2IA120.6
C12D—C13D—C14D121.4 (2)C3I—C2I—H2IA120.6
C12D—C13D—H13D119.3C4I—C3I—C2I121.7 (2)
C14D—C13D—H13D119.3C4I—C3I—Cl1I119.16 (17)
C15D—C14D—C13D117.7 (2)C2I—C3I—Cl1I119.10 (18)
C15D—C14D—C17D121.1 (2)C5I—C4I—C3I118.9 (2)
C13D—C14D—C17D121.2 (2)C5I—C4I—H4IA120.5
C14D—C15D—C16D121.2 (2)C3I—C4I—H4IA120.5
C14D—C15D—H15D119.4C4I—C5I—C6I121.0 (2)
C16D—C15D—H15D119.4C4I—C5I—H5IA119.5
C11D—C16D—C15D120.9 (2)C6I—C5I—H5IA119.5
C11D—C16D—H16D119.5C1I—C6I—C5I118.6 (2)
C15D—C16D—H16D119.5C1I—C6I—C7I122.74 (19)
C14D—C17D—C18D115.32 (19)C5I—C6I—C7I118.63 (19)
C14D—C17D—H17F108.4N4I—C7I—C6I120.53 (19)
C18D—C17D—H17F108.4N4I—C7I—H7IA119.7
C14D—C17D—H17G108.4C6I—C7I—H7IA119.7
C18D—C17D—H17G108.4N1I—C8I—N3I102.65 (17)
H17F—C17D—H17G107.5N1I—C8I—S1I127.94 (17)
C20D—C18D—C17D114.2 (2)N3I—C8I—S1I129.32 (16)
C20D—C18D—C19D111.0 (2)N2I—C9I—N3I110.48 (18)
C17D—C18D—C19D110.7 (2)N2I—C9I—C10I125.84 (19)
C20D—C18D—H18D106.8N3I—C9I—C10I123.68 (19)
C17D—C18D—H18D106.8C9I—C10I—C11I112.16 (16)
C19D—C18D—H18D106.8C9I—C10I—C21I109.69 (18)
C18D—C19D—H19M109.5C11I—C10I—C21I111.88 (17)
C18D—C19D—H19N109.5C9I—C10I—H10I107.6
H19M—C19D—H19N109.5C11I—C10I—H10I107.6
C18D—C19D—H19O109.5C21I—C10I—H10I107.6
H19M—C19D—H19O109.5C16I—C11I—C12I117.9 (2)
H19N—C19D—H19O109.5C16I—C11I—C10I121.08 (18)
C18D—C20D—H20M109.5C12I—C11I—C10I121.01 (19)
C18D—C20D—H20N109.5C13I—C12I—C11I120.8 (2)
H20M—C20D—H20N109.5C13I—C12I—H12I119.6
C18D—C20D—H20O109.5C11I—C12I—H12I119.6
H20M—C20D—H20O109.5C12I—C13I—C14I121.5 (2)
H20N—C20D—H20O109.5C12I—C13I—H13I119.2
C10D—C21D—H21J109.5C14I—C13I—H13I119.2
C10D—C21D—H21K109.5C13I—C14I—C15I117.5 (2)
H21J—C21D—H21K109.5C13I—C14I—C17I121.4 (2)
C10D—C21D—H21L109.5C15I—C14I—C17I121.1 (2)
H21J—C21D—H21L109.5C16I—C15I—C14I121.4 (2)
H21K—C21D—H21L109.5C16I—C15I—H15I119.3
C8E—N1E—N2E114.19 (17)C14I—C15I—H15I119.3
C8E—N1E—H1EB122.9C15I—C16I—C11I120.9 (2)
N2E—N1E—H1EB122.9C15I—C16I—H16I119.6
C9E—N2E—N1E104.14 (17)C11I—C16I—H16I119.6
C8E—N3E—C9E108.02 (17)C14I—C17I—C18I113.82 (18)
C8E—N3E—N4E132.23 (16)C14I—C17I—H17T108.8
C9E—N3E—N4E119.29 (16)C18I—C17I—H17T108.8
C7E—N4E—N3E117.06 (17)C14I—C17I—H17U108.8
C2E—C1E—C6E120.8 (2)C18I—C17I—H17U108.8
C2E—C1E—H1EA119.6H17T—C17I—H17U107.7
C6E—C1E—H1EA119.6C20I—C18I—C19I110.63 (19)
C1E—C2E—C3E118.6 (2)C20I—C18I—C17I111.09 (19)
C1E—C2E—H2EA120.7C19I—C18I—C17I110.35 (18)
C3E—C2E—H2EA120.7C20I—C18I—H18I108.2
C4E—C3E—C2E121.8 (2)C19I—C18I—H18I108.2
C4E—C3E—Cl1E118.83 (19)C17I—C18I—H18I108.2
C2E—C3E—Cl1E119.4 (2)C18I—C19I—H192109.5
C3E—C4E—C5E119.2 (2)C18I—C19I—H193109.5
C3E—C4E—H4EA120.4H192—C19I—H193109.5
C5E—C4E—H4EA120.4C18I—C19I—H194109.5
C4E—C5E—C6E120.6 (2)H192—C19I—H194109.5
C4E—C5E—H5EA119.7H193—C19I—H194109.5
C6E—C5E—H5EA119.7C18I—C20I—H21Z109.5
C1E—C6E—C5E119.1 (2)C18I—C20I—H22A109.5
C1E—C6E—C7E122.86 (19)H21Z—C20I—H22A109.5
C5E—C6E—C7E118.05 (19)C18I—C20I—H22B109.5
N4E—C7E—C6E119.29 (19)H21Z—C20I—H22B109.5
N4E—C7E—H7EA120.4H22A—C20I—H22B109.5
C6E—C7E—H7EA120.4C10I—C21I—H22C109.5
N1E—C8E—N3E102.67 (17)C10I—C21I—H22D109.5
N1E—C8E—S1E126.68 (16)H22C—C21I—H22D109.5
N3E—C8E—S1E130.60 (16)C10I—C21I—H22E109.5
N2E—C9E—N3E110.93 (18)H22C—C21I—H22E109.5
N2E—C9E—C10E125.83 (19)H22D—C21I—H22E109.5
N3E—C9E—C10E123.17 (19)
C8A—N1A—N2A—C9A−1.0 (2)N4E—N3E—C8E—S1E3.5 (3)
C8A—N3A—N4A—C7A−38.0 (3)N1E—N2E—C9E—N3E−0.8 (2)
C9A—N3A—N4A—C7A153.48 (18)N1E—N2E—C9E—C10E−177.80 (19)
C6A—C1A—C2A—C3A0.0 (3)C8E—N3E—C9E—N2E1.9 (2)
C1A—C2A—C3A—C4A0.6 (3)N4E—N3E—C9E—N2E175.02 (16)
C1A—C2A—C3A—Cl1A−178.34 (16)C8E—N3E—C9E—C10E179.00 (18)
C2A—C3A—C4A—C5A−0.8 (3)N4E—N3E—C9E—C10E−7.9 (3)
Cl1A—C3A—C4A—C5A178.16 (15)N2E—C9E—C10E—C11E98.4 (2)
C3A—C4A—C5A—C6A0.3 (3)N3E—C9E—C10E—C11E−78.3 (2)
C4A—C5A—C6A—C1A0.2 (3)N2E—C9E—C10E—C21E−25.5 (3)
C4A—C5A—C6A—C7A−178.57 (18)N3E—C9E—C10E—C21E157.83 (18)
C2A—C1A—C6A—C5A−0.4 (3)C9E—C10E—C11E—C16E114.4 (2)
C2A—C1A—C6A—C7A178.34 (19)C21E—C10E—C11E—C16E−123.0 (2)
N3A—N4A—C7A—C6A179.79 (16)C9E—C10E—C11E—C12E−66.1 (2)
C5A—C6A—C7A—N4A−170.67 (19)C21E—C10E—C11E—C12E56.5 (2)
C1A—C6A—C7A—N4A10.6 (3)C16E—C11E—C12E—C13E0.9 (3)
N2A—N1A—C8A—N3A2.5 (2)C10E—C11E—C12E—C13E−178.59 (18)
N2A—N1A—C8A—S1A−173.89 (15)C11E—C12E—C13E—C14E−1.0 (3)
C9A—N3A—C8A—N1A−2.9 (2)C12E—C13E—C14E—C15E0.6 (3)
N4A—N3A—C8A—N1A−172.66 (18)C12E—C13E—C14E—C17E−179.68 (19)
C9A—N3A—C8A—S1A173.38 (16)C13E—C14E—C15E—C16E−0.1 (3)
N4A—N3A—C8A—S1A3.7 (3)C17E—C14E—C15E—C16E−179.88 (19)
N1A—N2A—C9A—N3A−1.0 (2)C14E—C15E—C16E—C11E0.1 (3)
N1A—N2A—C9A—C10A177.51 (19)C12E—C11E—C16E—C15E−0.5 (3)
C8A—N3A—C9A—N2A2.6 (2)C10E—C11E—C16E—C15E179.01 (18)
N4A—N3A—C9A—N2A173.44 (17)C13E—C14E—C17E—C18E95.5 (2)
C8A—N3A—C9A—C10A−175.99 (18)C15E—C14E—C17E—C18E−84.7 (3)
N4A—N3A—C9A—C10A−5.2 (3)C14E—C17E—C18E—C20E−63.8 (2)
N2A—C9A—C10A—C11A102.4 (2)C14E—C17E—C18E—C19E173.6 (2)
N3A—C9A—C10A—C11A−79.2 (2)C8F—N1F—N2F—C9F−1.1 (2)
N2A—C9A—C10A—C21A−22.0 (3)C8F—N3F—N4F—C7F−27.3 (3)
N3A—C9A—C10A—C21A156.34 (19)C9F—N3F—N4F—C7F160.66 (18)
C9A—C10A—C11A—C16A119.5 (2)C6F—C1F—C2F—C3F0.4 (3)
C21A—C10A—C11A—C16A−116.4 (2)C1F—C2F—C3F—C4F0.1 (3)
C9A—C10A—C11A—C12A−63.0 (2)C1F—C2F—C3F—Cl1F179.98 (16)
C21A—C10A—C11A—C12A61.2 (2)C2F—C3F—C4F—C5F−0.8 (3)
C16A—C11A—C12A—C13A1.4 (3)Cl1F—C3F—C4F—C5F179.36 (16)
C10A—C11A—C12A—C13A−176.23 (18)C3F—C4F—C5F—C6F0.9 (3)
C11A—C12A—C13A—C14A−0.2 (3)C4F—C5F—C6F—C1F−0.4 (3)
C12A—C13A—C14A—C15A−0.7 (3)C4F—C5F—C6F—C7F−178.90 (19)
C12A—C13A—C14A—C17A177.0 (2)C2F—C1F—C6F—C5F−0.3 (3)
C13A—C14A—C15A—C16A0.2 (3)C2F—C1F—C6F—C7F178.16 (19)
C17A—C14A—C15A—C16A−177.4 (2)N3F—N4F—C7F—C6F−178.16 (16)
C14A—C15A—C16A—C11A1.1 (3)C5F—C6F—C7F—N4F−167.62 (19)
C12A—C11A—C16A—C15A−1.9 (3)C1F—C6F—C7F—N4F13.9 (3)
C10A—C11A—C16A—C15A175.78 (18)N2F—N1F—C8F—N3F2.5 (2)
C13A—C14A—C17A—C18A−72.5 (3)N2F—N1F—C8F—S1F−175.03 (15)
C15A—C14A—C17A—C18A105.1 (3)C9F—N3F—C8F—N1F−2.8 (2)
C14A—C17A—C18A—C20A−55.5 (3)N4F—N3F—C8F—N1F−175.50 (18)
C14A—C17A—C18A—C19A178.3 (3)C9F—N3F—C8F—S1F174.51 (16)
C8B—N1B—N2B—C9B1.1 (2)N4F—N3F—C8F—S1F1.9 (3)
C8B—N3B—N4B—C7B26.7 (3)N1F—N2F—C9F—N3F−0.9 (2)
C9B—N3B—N4B—C7B−160.85 (18)N1F—N2F—C9F—C10F178.77 (19)
C6B—C1B—C2B—C3B−1.1 (3)C8F—N3F—C9F—N2F2.4 (2)
C1B—C2B—C3B—C4B1.4 (3)N4F—N3F—C9F—N2F176.25 (16)
C1B—C2B—C3B—Cl1B−178.41 (16)C8F—N3F—C9F—C10F−177.23 (18)
C2B—C3B—C4B—C5B−0.1 (3)N4F—N3F—C9F—C10F−3.4 (3)
Cl1B—C3B—C4B—C5B179.68 (16)N2F—C9F—C10F—C11F97.1 (2)
C3B—C4B—C5B—C6B−1.5 (3)N3F—C9F—C10F—C11F−83.3 (2)
C2B—C1B—C6B—C5B−0.5 (3)N2F—C9F—C10F—C21F−26.7 (3)
C2B—C1B—C6B—C7B−178.14 (19)N3F—C9F—C10F—C21F152.90 (19)
C4B—C5B—C6B—C1B1.8 (3)C9F—C10F—C11F—C16F118.0 (2)
C4B—C5B—C6B—C7B179.50 (19)C21F—C10F—C11F—C16F−119.3 (2)
N3B—N4B—C7B—C6B177.14 (16)C9F—C10F—C11F—C12F−64.9 (2)
C1B—C6B—C7B—N4B−12.5 (3)C21F—C10F—C11F—C12F57.8 (2)
C5B—C6B—C7B—N4B169.91 (18)C16F—C11F—C12F—C13F0.8 (3)
N2B—N1B—C8B—N3B−2.4 (2)C10F—C11F—C12F—C13F−176.46 (18)
N2B—N1B—C8B—S1B175.16 (15)C11F—C12F—C13F—C14F−0.5 (3)
C9B—N3B—C8B—N1B2.8 (2)C12F—C13F—C14F—C15F−0.1 (3)
N4B—N3B—C8B—N1B175.81 (18)C12F—C13F—C14F—C17F179.92 (19)
C9B—N3B—C8B—S1B−174.68 (16)C13F—C14F—C15F—C16F0.3 (3)
N4B—N3B—C8B—S1B−1.6 (3)C17F—C14F—C15F—C16F−179.69 (19)
N1B—N2B—C9B—N3B0.8 (2)C14F—C15F—C16F—C11F0.0 (3)
N1B—N2B—C9B—C10B−179.74 (19)C12F—C11F—C16F—C15F−0.6 (3)
C8B—N3B—C9B—N2B−2.4 (2)C10F—C11F—C16F—C15F176.64 (18)
N4B—N3B—C9B—N2B−176.51 (16)C13F—C14F—C17F—C18F97.2 (2)
C8B—N3B—C9B—C10B178.19 (18)C15F—C14F—C17F—C18F−82.8 (3)
N4B—N3B—C9B—C10B4.0 (3)C14F—C17F—C18F—C20F−63.3 (3)
N2B—C9B—C10B—C11B−105.3 (2)C14F—C17F—C18F—C19F173.6 (2)
N3B—C9B—C10B—C11B74.0 (2)C8G—N1G—N2G—C9G0.4 (2)
N2B—C9B—C10B—C21B18.4 (3)C8G—N3G—N4G—C7G40.0 (3)
N3B—C9B—C10B—C21B−162.29 (18)C9G—N3G—N4G—C7G−153.14 (18)
C9B—C10B—C11B—C16B−125.0 (2)C6G—C1G—C2G—C3G1.2 (3)
C21B—C10B—C11B—C16B112.1 (2)C1G—C2G—C3G—C4G−1.5 (3)
C9B—C10B—C11B—C12B57.0 (3)C1G—C2G—C3G—Cl1G178.69 (16)
C21B—C10B—C11B—C12B−65.9 (2)C2G—C3G—C4G—C5G0.9 (3)
C16B—C11B—C12B—C13B0.2 (3)Cl1G—C3G—C4G—C5G−179.34 (16)
C10B—C11B—C12B—C13B178.24 (18)C3G—C4G—C5G—C6G0.1 (3)
C11B—C12B—C13B—C14B−0.1 (3)C4G—C5G—C6G—C1G−0.4 (3)
C12B—C13B—C14B—C15B−0.1 (3)C4G—C5G—C6G—C7G179.42 (19)
C12B—C13B—C14B—C17B−177.75 (19)C2G—C1G—C6G—C5G−0.2 (3)
C13B—C14B—C15B—C16B0.1 (3)C2G—C1G—C6G—C7G179.93 (19)
C17B—C14B—C15B—C16B177.7 (2)N3G—N4G—C7G—C6G−177.98 (16)
C12B—C11B—C16B—C15B−0.2 (3)C5G—C6G—C7G—N4G175.69 (18)
C10B—C11B—C16B—C15B−178.22 (18)C1G—C6G—C7G—N4G−4.5 (3)
C14B—C15B—C16B—C11B0.0 (3)N2G—N1G—C8G—N3G−1.7 (2)
C13B—C14B—C17B—C18B68.9 (3)N2G—N1G—C8G—S1G175.02 (15)
C15B—C14B—C17B—C18B−108.6 (3)C9G—N3G—C8G—N1G2.2 (2)
C13B—C14B—C17B—C18X108.6 (5)N4G—N3G—C8G—N1G170.47 (17)
C15B—C14B—C17B—C18X−69.0 (6)C9G—N3G—C8G—S1G−174.39 (16)
C14B—C17B—C18B—C19B45.6 (4)N4G—N3G—C8G—S1G−6.1 (3)
C18X—C17B—C18B—C19B−58.0 (6)N1G—N2G—C9G—N3G1.1 (2)
C14B—C17B—C18B—C20B175.5 (3)N1G—N2G—C9G—C10G179.70 (18)
C18X—C17B—C18B—C20B72.0 (6)C8G—N3G—C9G—N2G−2.1 (2)
C14B—C17B—C18X—C19X−23.2 (16)N4G—N3G—C9G—N2G−171.58 (16)
C18B—C17B—C18X—C19X70.6 (14)C8G—N3G—C9G—C10G179.18 (18)
C14B—C17B—C18X—C20X−172.3 (6)N4G—N3G—C9G—C10G9.7 (3)
C18B—C17B—C18X—C20X−78.4 (8)N2G—C9G—C10G—C11G−102.0 (2)
C8C—N1C—N2C—C9C−0.9 (2)N3G—C9G—C10G—C11G76.5 (2)
C8C—N3C—N4C—C7C−26.4 (3)N2G—C9G—C10G—C21G22.2 (3)
C9C—N3C—N4C—C7C161.12 (18)N3G—C9G—C10G—C21G−159.32 (18)
C6C—C1C—C2C—C3C0.0 (3)C9G—C10G—C11G—C16G−119.3 (2)
C1C—C2C—C3C—C4C0.1 (3)C21G—C10G—C11G—C16G117.4 (2)
C1C—C2C—C3C—Cl1C179.25 (16)C9G—C10G—C11G—C12G61.4 (2)
C2C—C3C—C4C—C5C−0.7 (3)C21G—C10G—C11G—C12G−61.9 (2)
Cl1C—C3C—C4C—C5C−179.90 (16)C16G—C11G—C12G—C13G0.5 (3)
C3C—C4C—C5C—C6C1.3 (3)C10G—C11G—C12G—C13G179.80 (18)
C4C—C5C—C6C—C1C−1.1 (3)C11G—C12G—C13G—C14G0.0 (3)
C4C—C5C—C6C—C7C−179.52 (18)C12G—C13G—C14G—C15G−0.6 (3)
C2C—C1C—C6C—C5C0.4 (3)C12G—C13G—C14G—C17G178.9 (2)
C2C—C1C—C6C—C7C178.83 (19)C13G—C14G—C15G—C16G0.8 (3)
N3C—N4C—C7C—C6C−177.29 (16)C17G—C14G—C15G—C16G−178.7 (2)
C5C—C6C—C7C—N4C−167.63 (18)C14G—C15G—C16G—C11G−0.4 (3)
C1C—C6C—C7C—N4C14.0 (3)C12G—C11G—C16G—C15G−0.2 (3)
N2C—N1C—C8C—N3C2.4 (2)C10G—C11G—C16G—C15G−179.59 (18)
N2C—N1C—C8C—S1C−175.25 (15)C15G—C14G—C17G—C18G−75.6 (3)
C9C—N3C—C8C—N1C−2.9 (2)C13G—C14G—C17G—C18G104.9 (3)
N4C—N3C—C8C—N1C−175.97 (19)C14G—C17G—C18G—C20G−41.9 (5)
C9C—N3C—C8C—S1C174.67 (16)C14G—C17G—C18G—C19G−177.7 (3)
N4C—N3C—C8C—S1C1.6 (3)C8H—N1H—N2H—C9H−1.1 (2)
N1C—N2C—C9C—N3C−1.0 (2)C8H—N3H—N4H—C7H−33.6 (3)
N1C—N2C—C9C—C10C−179.25 (19)C9H—N3H—N4H—C7H156.05 (18)
C8C—N3C—C9C—N2C2.6 (2)C6H—C1H—C2H—C3H0.0 (3)
N4C—N3C—C9C—N2C176.81 (16)C1H—C2H—C3H—C4H1.4 (3)
C8C—N3C—C9C—C10C−179.15 (18)C1H—C2H—C3H—Cl1H−177.98 (16)
N4C—N3C—C9C—C10C−4.9 (3)C2H—C3H—C4H—C5H−1.5 (3)
N2C—C9C—C10C—C11C106.1 (2)Cl1H—C3H—C4H—C5H177.87 (16)
N3C—C9C—C10C—C11C−71.9 (2)C3H—C4H—C5H—C6H0.2 (3)
N2C—C9C—C10C—C21C−17.3 (3)C2H—C1H—C6H—C5H−1.2 (3)
N3C—C9C—C10C—C21C164.63 (18)C2H—C1H—C6H—C7H177.29 (19)
C9C—C10C—C11C—C16C130.7 (2)C4H—C5H—C6H—C1H1.0 (3)
C21C—C10C—C11C—C16C−106.5 (2)C4H—C5H—C6H—C7H−177.50 (18)
C9C—C10C—C11C—C12C−51.4 (3)N3H—N4H—C7H—C6H−179.00 (16)
C21C—C10C—C11C—C12C71.4 (2)C1H—C6H—C7H—N4H7.3 (3)
C16C—C11C—C12C—C13C−0.1 (3)C5H—C6H—C7H—N4H−174.28 (19)
C10C—C11C—C12C—C13C−178.07 (18)N2H—N1H—C8H—N3H2.6 (2)
C11C—C12C—C13C—C14C0.1 (3)N2H—N1H—C8H—S1H−174.78 (15)
C12C—C13C—C14C—C15C−0.1 (3)C9H—N3H—C8H—N1H−2.9 (2)
C12C—C13C—C14C—C17C177.3 (2)N4H—N3H—C8H—N1H−174.13 (18)
C13C—C14C—C15C—C16C0.0 (3)C9H—N3H—C8H—S1H174.33 (16)
C17C—C14C—C15C—C16C−177.4 (2)N4H—N3H—C8H—S1H3.1 (3)
C14C—C15C—C16C—C11C0.0 (3)N1H—N2H—C9H—N3H−0.9 (2)
C12C—C11C—C16C—C15C0.1 (3)N1H—N2H—C9H—C10H179.89 (19)
C10C—C11C—C16C—C15C177.99 (19)C8H—N3H—C9H—N2H2.5 (2)
C13C—C14C—C17C—C18C−63.8 (3)N4H—N3H—C9H—N2H174.82 (16)
C15C—C14C—C17C—C18C113.5 (3)C8H—N3H—C9H—C10H−178.25 (18)
C14C—C17C—C18C—C19C−50.4 (3)N4H—N3H—C9H—C10H−5.9 (3)
C14C—C17C—C18C—C20C−175.1 (2)N2H—C9H—C10H—C11H98.5 (2)
C8D—N1D—N2D—C9D0.6 (2)N3H—C9H—C10H—C11H−80.7 (2)
C8D—N3D—N4D—C7D38.7 (3)N2H—C9H—C10H—C21H−26.9 (3)
C9D—N3D—N4D—C7D−153.84 (18)N3H—C9H—C10H—C21H153.90 (19)
C6D—C1D—C2D—C3D1.1 (3)C9H—C10H—C11H—C12H−72.8 (2)
C1D—C2D—C3D—C4D−1.1 (3)C21H—C10H—C11H—C12H51.1 (3)
C1D—C2D—C3D—Cl1D179.03 (16)C9H—C10H—C11H—C16H108.7 (2)
C2D—C3D—C4D—C5D0.7 (3)C21H—C10H—C11H—C16H−127.5 (2)
Cl1D—C3D—C4D—C5D−179.51 (16)C16H—C11H—C12H—C13H0.3 (3)
C3D—C4D—C5D—C6D−0.1 (3)C10H—C11H—C12H—C13H−178.33 (18)
C2D—C1D—C6D—C5D−0.6 (3)C11H—C12H—C13H—C14H0.3 (3)
C2D—C1D—C6D—C7D179.71 (19)C12H—C13H—C14H—C15H−0.5 (3)
C4D—C5D—C6D—C1D0.1 (3)C12H—C13H—C14H—C17H−179.49 (19)
C4D—C5D—C6D—C7D179.81 (19)C13H—C14H—C15H—C16H0.1 (3)
N3D—N4D—C7D—C6D−179.68 (16)C17H—C14H—C15H—C16H179.10 (19)
C1D—C6D—C7D—N4D−6.8 (3)C14H—C15H—C16H—C11H0.5 (3)
C5D—C6D—C7D—N4D173.47 (19)C12H—C11H—C16H—C15H−0.7 (3)
N2D—N1D—C8D—N3D−2.2 (2)C10H—C11H—C16H—C15H177.94 (18)
N2D—N1D—C8D—S1D174.31 (15)C13H—C14H—C17H—C18H101.3 (2)
C9D—N3D—C8D—N1D2.9 (2)C15H—C14H—C17H—C18H−77.6 (3)
N4D—N3D—C8D—N1D171.54 (18)C14H—C17H—C18H—C20H−60.8 (2)
C9D—N3D—C8D—S1D−173.61 (16)C14H—C17H—C18H—C19H176.25 (19)
N4D—N3D—C8D—S1D−4.9 (3)C8I—N1I—N2I—C9I−1.0 (2)
N1D—N2D—C9D—N3D1.3 (2)C8I—N3I—N4I—C7I−39.2 (3)
N1D—N2D—C9D—C10D−178.53 (19)C9I—N3I—N4I—C7I151.99 (18)
C8D—N3D—C9D—N2D−2.7 (2)C6I—C1I—C2I—C3I−0.5 (3)
N4D—N3D—C9D—N2D−172.69 (16)C1I—C2I—C3I—C4I1.4 (3)
C8D—N3D—C9D—C10D177.12 (18)C1I—C2I—C3I—Cl1I−178.51 (16)
N4D—N3D—C9D—C10D7.2 (3)C2I—C3I—C4I—C5I−1.3 (3)
N2D—C9D—C10D—C11D−107.3 (2)Cl1I—C3I—C4I—C5I178.67 (16)
N3D—C9D—C10D—C11D72.9 (2)C3I—C4I—C5I—C6I0.2 (3)
N2D—C9D—C10D—C21D17.5 (3)C2I—C1I—C6I—C5I−0.5 (3)
N3D—C9D—C10D—C21D−162.32 (18)C2I—C1I—C6I—C7I178.65 (19)
C9D—C10D—C11D—C16D−120.5 (2)C4I—C5I—C6I—C1I0.7 (3)
C21D—C10D—C11D—C16D115.2 (2)C4I—C5I—C6I—C7I−178.52 (19)
C9D—C10D—C11D—C12D62.1 (2)N3I—N4I—C7I—C6I179.33 (16)
C21D—C10D—C11D—C12D−62.3 (2)C1I—C6I—C7I—N4I6.3 (3)
C16D—C11D—C12D—C13D−0.4 (3)C5I—C6I—C7I—N4I−174.55 (19)
C10D—C11D—C12D—C13D177.09 (18)N2I—N1I—C8I—N3I3.0 (2)
C11D—C12D—C13D—C14D−0.8 (3)N2I—N1I—C8I—S1I−173.70 (16)
C12D—C13D—C14D—C15D1.0 (3)C9I—N3I—C8I—N1I−3.7 (2)
C12D—C13D—C14D—C17D−178.55 (19)N4I—N3I—C8I—N1I−173.59 (18)
C13D—C14D—C15D—C16D−0.1 (3)C9I—N3I—C8I—S1I172.94 (16)
C17D—C14D—C15D—C16D179.48 (19)N4I—N3I—C8I—S1I3.0 (3)
C12D—C11D—C16D—C15D1.3 (3)N1I—N2I—C9I—N3I−1.5 (2)
C10D—C11D—C16D—C15D−176.17 (18)N1I—N2I—C9I—C10I177.74 (19)
C14D—C15D—C16D—C11D−1.1 (3)C8I—N3I—C9I—N2I3.4 (2)
C15D—C14D—C17D—C18D−117.8 (2)N4I—N3I—C9I—N2I174.36 (17)
C13D—C14D—C17D—C18D61.7 (3)C8I—N3I—C9I—C10I−175.84 (18)
C14D—C17D—C18D—C20D54.2 (3)N4I—N3I—C9I—C10I−4.9 (3)
C14D—C17D—C18D—C19D−179.6 (2)N2I—C9I—C10I—C11I97.1 (2)
C8E—N1E—N2E—C9E−0.6 (2)N3I—C9I—C10I—C11I−83.8 (2)
C8E—N3E—N4E—C7E−29.4 (3)N2I—C9I—C10I—C21I−27.9 (3)
C9E—N3E—N4E—C7E159.46 (18)N3I—C9I—C10I—C21I151.21 (19)
C6E—C1E—C2E—C3E0.4 (3)C9I—C10I—C11I—C16I107.3 (2)
C1E—C2E—C3E—C4E0.3 (3)C21I—C10I—C11I—C16I−129.0 (2)
C1E—C2E—C3E—Cl1E−178.77 (16)C9I—C10I—C11I—C12I−75.5 (2)
C2E—C3E—C4E—C5E−0.7 (3)C21I—C10I—C11I—C12I48.3 (3)
Cl1E—C3E—C4E—C5E178.35 (17)C16I—C11I—C12I—C13I1.0 (3)
C3E—C4E—C5E—C6E0.4 (3)C10I—C11I—C12I—C13I−176.34 (19)
C2E—C1E—C6E—C5E−0.7 (3)C11I—C12I—C13I—C14I0.1 (3)
C2E—C1E—C6E—C7E177.17 (19)C12I—C13I—C14I—C15I−0.9 (3)
C4E—C5E—C6E—C1E0.3 (3)C12I—C13I—C14I—C17I−179.87 (19)
C4E—C5E—C6E—C7E−177.70 (19)C13I—C14I—C15I—C16I0.5 (3)
N3E—N4E—C7E—C6E−178.41 (16)C17I—C14I—C15I—C16I179.47 (19)
C1E—C6E—C7E—N4E10.7 (3)C14I—C15I—C16I—C11I0.7 (3)
C5E—C6E—C7E—N4E−171.40 (19)C12I—C11I—C16I—C15I−1.4 (3)
N2E—N1E—C8E—N3E1.7 (2)C10I—C11I—C16I—C15I175.94 (18)
N2E—N1E—C8E—S1E−175.93 (15)C13I—C14I—C17I—C18I105.0 (2)
C9E—N3E—C8E—N1E−2.1 (2)C15I—C14I—C17I—C18I−73.9 (3)
N4E—N3E—C8E—N1E−173.99 (18)C14I—C17I—C18I—C20I−59.6 (3)
C9E—N3E—C8E—S1E175.43 (17)C14I—C17I—C18I—C19I177.32 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AB···S1Fi0.862.523.373 (2)170
N1B—H1BB···S1Cii0.862.473.3072 (19)163
N1C—H1CB···S1Biii0.862.453.285 (2)165
N1D—H1DB···S1Eiv0.862.483.3289 (19)171
N1E—H1EB···S1Dv0.862.413.253 (2)168
N1F—H1FB···S1Ai0.862.413.256 (2)167
N1G—H1GB···S1Hiv0.862.433.287 (2)174
N1H—H1HB···S1Gv0.862.453.3047 (19)170
N1I—H1IB···S1Ivi0.862.453.301 (2)172
C10D—H10D···S1Civ0.982.873.769 (2)152
C10G—H10G···S1Fiv0.982.823.662 (2)144
C7A—H7AA···S1A0.932.583.174 (2)122
C7B—H7BA···S1B0.932.573.240 (2)130
C7C—H7CA···S1C0.932.583.254 (2)130
C7D—H7DA···S1D0.932.593.174 (2)121
C7E—H7EA···S1E0.932.563.223 (2)129
C7F—H7FA···S1F0.932.563.229 (2)130
C7G—H7GA···S1G0.932.613.178 (2)120
C7H—H7HA···S1H0.932.553.187 (2)126
C7I—H7IA···S1I0.932.613.179 (2)120
C4D—H4DA···Cg10.932.723.588 (2)156
C4E—H4EA···Cg20.932.843.566 (3)136
C4G—H4GA···Cg30.932.863.701 (2)152
C4H—H4HA···Cg40.932.513.338 (2)148
C4A—H4AA···Cg5vi0.932.723.606 (2)159
C4C—H4CA···Cg6vii0.932.963.670 (2)134
C4F—H4FA···Cg7vi0.932.783.524 (3)137
C4I—H4IA···Cg8viii0.932.883.719 (2)151
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y+1, z; (iii) x−1, y−1, z; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) x, y−1, z; (viii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC21H23ClN4S
Mr398.94
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)13.1781 (2), 23.7731 (4), 30.8550 (5)
α, β, γ (°)92.861 (1), 101.520 (1), 92.254 (1)
V (Å3)9447.8 (3)
Z18
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.55 × 0.34 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.855, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections		157626, 38430, 27090
Rint0.044
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.139, 1.01
No. of reflections38430
No. of parameters2230
No. of restraints71
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.84, −0.63

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AB···S1Fi0.862.523.373 (2)170
N1B—H1BB···S1Cii0.862.473.3072 (19)163
N1C—H1CB···S1Biii0.862.453.285 (2)165
N1D—H1DB···S1Eiv0.862.483.3289 (19)171
N1E—H1EB···S1Dv0.862.413.253 (2)168
N1F—H1FB···S1Ai0.862.413.256 (2)167
N1G—H1GB···S1Hiv0.862.433.287 (2)174
N1H—H1HB···S1Gv0.862.453.3047 (19)170
N1I—H1IB···S1Ivi0.862.453.301 (2)172
C10D—H10D···S1Civ0.982.873.769 (2)152
C10G—H10G···S1Fiv0.982.823.662 (2)144
C7A—H7AA···S1A0.932.583.174 (2)122
C7B—H7BA···S1B0.932.573.240 (2)130
C7C—H7CA···S1C0.932.583.254 (2)130
C7D—H7DA···S1D0.932.593.174 (2)121
C7E—H7EA···S1E0.932.563.223 (2)129
C7F—H7FA···S1F0.932.563.229 (2)130
C7G—H7GA···S1G0.932.613.178 (2)120
C7H—H7HA···S1H0.932.553.187 (2)126
C7I—H7IA···S1I0.932.613.179 (2)120
C4D—H4DA···Cg10.932.723.588 (2)156
C4E—H4EA···Cg20.932.843.566 (3)136
C4G—H4GA···Cg30.932.863.701 (2)152
C4H—H4HA···Cg40.932.513.338 (2)148
C4A—H4AA···Cg5vi0.932.723.606 (2)159
C4C—H4CA···Cg6vii0.932.963.670 (2)134
C4F—H4FA···Cg7vi0.932.783.524 (3)137
C4I—H4IA···Cg8viii0.932.883.719 (2)151
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y+1, z; (iii) x−1, y−1, z; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) x, y−1, z; (viii) −x+2, −y+1, −z+1.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5473-2009. Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1242-o1243
doi:10.1107/S160053680901650X
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