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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 75| Part 2| February 2019| Pages 255-259
https://doi.org/10.1107/S2056989019000975

Crystal structure of 6-(4-chloro­phen­yl)-6a-nitro-6a,6b,8,9,10,12a-hexa­hydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11′-indeno­[1,2-b]quinoxaline]

CROSSMARK_Color_square_no_text.svg
S. Syed Abuthahir,a M. NizamMohideen,a* V. Viswanathan,b D. Velmuruganc and J. Nagasivaraod

aPG & Research Department of Physics, The New College (Autonomous), Chennai 600 014, Tamil Nadu, India, bDepartment of Biophysics, All India Institute of Medical Science, New Delhi 110 029, India, cCAS in Crystallography and Biophysics, University of Madras, Chennai 600 025, India, and dGVK Biosciences Pvt. Ltd, Hyderabad 500 076, India
*Correspondence e-mail: mnizam.new@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 16 January 2019; accepted 19 January 2019; online 25 January 2019)

The title compound, C35H27ClN4O3, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. In both mol­ecules, the pyran and pyridine rings adopt envelope and chair conformations, respectively. The conformation of the pyrrolidine and cyclo­pentene rings differ in the two mol­ecules; twisted and flat, respectively, in mol­ecule A, but envelope and twisted, respectively, in mol­ecule B. In both mol­ecules, there is a C—H⋯N intra­molecular hydrogen bond present. In both mol­ecules, the oxygen atoms of the nitro groups are disordered as is the chlorine atom in mol­ecule B. In the crystal, the B mol­ecules are linked by C—H⋯O hydrogen bonds, forming –B–B–B– chains along [010], and by C—H⋯π inter­actions. The A and B mol­ecules are also linked by a number of C—H⋯π inter­actions, resulting in the formation a supra­molecular three-dimensional structure. In mol­ecule A, the nitro group oxygen atoms are disordered over two positions with refined occupancy ratios of the nitro group oxygen atoms O3A and O4A in 0.59 (2):0.41 (2) while in molecule B one of the nitro O atoms is disordered over two positions with a refined occupancy ratio of 0.686 (13):0.314 (13) and the chlorine atoms is disordered over two positions with a refined occupancy ratio of 0.72 (3):0.28 (3).

CCDC reference: 1024832

Similar articles

1. Chemical context

Nitro­gen-containing heterocyclic compounds are reported to possess a diverse range of biological activities such as anti­microbial, anti­tumor and anti-inflammatory (Syed Abuthahir et al., 2019[Syed Abuthahir, S., NizamMohideen, M., Viswanathan, V., Velmurugan, D. & Nagasivarao, J. (2019). Acta Cryst. E75, 218-222.]; Thirunavukkarsu et al., 2017[Thirunavukkarsu, A., Sujatha, T., Umarani, P. R., Nizam Mohideen, M., Silambarasan, A. & Kumar, R. M. (2017). J. Cryst. Growth, 460, 42-47.]) properties. Spiro compounds are often encountered in many pharmacologically active alkaloids (NizamMohideen et al., 2009c[NizamMohideen, M., Thenmozhi, S., SubbiahPandi, A., Savitha, G. & Perumal, P. T. (2009c). Acta Cryst. E65, o977-o978.]; Cravotto et al., 2001[Cravotto, G., Giovenzana, G. B., Pilati, T., Sisti, M. & Palmisano, G. (2001). J. Org. Chem. 66, 8447-8453.]). The cornerstone for cyclo­addition reactions, nitro­nes are excellent spin-trapping and highly versatile synthetic inter­mediates (Bernotas et al., 1996[Bernotas, R. C., Adams, G. & Carr, A. A. (1996). Tetrahedron, 52, 6519-6526.]; NizamMohideen et al., 2009b[NizamMohideen, M., Damodiran, M., SubbiahPandi, A. & Perumal, P. T. (2009b). Acta Cryst. E65, o2305-o2306.]). Highly substituted spiro compounds result from the 1,3-dipolar cyclo­addition of exocylic olefins with nitro­nes; these spiro compounds have also been transformed into complex heterocycles (Hossain et al., 1993[Hossain, N., Papchikhin, A., Plavec, J. & Chattopadhyaya, J. (1993). Tetrahedron, 49, 10133-10156.]; NizamMohideen et al., 2009a[NizamMohideen, M., Damodiran, M., SubbiahPandi, A. & Perumal, P. T. (2009a). Acta Cryst. E65, o1156.]). Recognizing the importance of such compounds in drug discovery and our ongoing research into the construction of novel heterocycles has prompted us to investigate the title compound: we report herein the synthesis and the crystal structure.[link]).

[Scheme 1]

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of rings C14B–C19B, C3B–C5B/C33B–C35B and C3A–C5A/C33A–C35A, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C20A—H20A⋯N4A 0.98 2.28 3.170 (3) 151
C20B—H20B⋯N4B 0.98 2.45 3.298 (3) 144
C33B—H33B⋯O3Bi 0.93 2.46 3.271 (5) 145
C8A—H8A⋯Cg1ii 0.93 2.69 3.536 (3) 151
C25B—H25C⋯Cg2iii 0.97 2.73 3.629 (3) 155
C31B—H31B⋯Cg3iv 0.93 2.99 3.742 (3) 139
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x, -y, -z+2; (iv) x-1, y, z.

2. Structural commentary

The mol­ecular structures and conformation of the two independent mol­ecules, A and B, in the asymmetric unit are shown in Figs. 1[link] and 2[link], respectively. In both mol­ecules, the oxygen atoms of the nitro groups are disordered as is the chlorine atom in mol­ecule B. For all further discussion only the major components of the disordered atoms will be considered. The bond lengths and angles are close to those reported for similar compounds (Devi et al., 2013a[Devi, S. K., Srinivasan, T., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2013a). Acta Cryst. E69, o1047.],b[Devi, S. K., Srinivasan, T., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2013b). Acta Cryst. E69, o993.]; Syed Abuthahir et al., 2019[Syed Abuthahir, S., NizamMohideen, M., Viswanathan, V., Velmurugan, D. & Nagasivarao, J. (2019). Acta Cryst. E75, 218-222.]). In both mol­ecules there is an C—H⋯N intra­molecular hydrogen bond present enclosing an S(7) ring motif (Fig. 1[link] and Table 1

[Figure 1]
Figure 1
View of the mol­ecular structure of mol­ecule A of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular C—H⋯N contact (Table 1[link]) is shown as an orange dashed line.
[Figure 2]
Figure 2
View of the mol­ecular structure of mol­ecule B of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular C—H⋯N contact (Table 1[link]) is shown as an orange dashed line.

The overall conformation of the two mol­ecules is very similar, as seen from the mol­ecule overlay figure (Fig. 3[link]), calculated and drawn using Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]). The essential difference concerns the conformations of the pyrrolidine (N1/C12/C13/C21/C22) and cyclo­pentene (C1/C2/C10–C12) rings. In mol­ecule A the former ring has an envelope conformation with atom C12A as the flap, while in mol­ecule B this ring has a twisted conformation on the N1B—C12B bond. The cyclo­pentene ring is twisted on the C12A—C1A bond in mol­ecule A but is flat in mol­ecule B. The pyran rings (O2/C19/C14/C13/C21/C20) in both mol­ecules have envelope conformations with atom C20 as the flap, and the piperidine rings in both mol­ecules (N1/C22–C26) have chair conformations.

[Figure 3]
Figure 3
A view of the mol­ecule overlay of inverted mol­ecule B (red) on mol­ecule A (blue), with an r.m.s. deviation of 0.208 Å. The H atoms have been omitted for clarity.

Chlorine atoms Cl1A and Cl2 deviate from the mean plane of the benzene rings to which they are attached (respectively C27A–C32A and C27B–C32B) by 0.006 (1) and 0.053 (16) Å, respectively. The mean plane of the five-membered pyrrolidine ring (N1/C12/C13/C21/C22) is inclined to the mean plane of the cyclo­pentene ring (C1/C2/C10–C12) by 87.30 (13) and 88.41 (11)° in mol­ecules A and B, respectively. The benzene rings C27–C32 and C14–C19 are inclined to each other by 58.13 (13)° in mol­ecule A and 57.13 (11)° in mol­ecule B, while benzene rings C6–C11 and C3–C5/C33–C35 are inclined to each other by 10.20 (13)° in mol­ecule A and 4.08 (13)° in mol­ecule B. The mean plane of the pyrrolidine ring (N1/C12/C13/C21/C22) makes a dihedral angle with the mean plane of the pyran ring (O2/C13/C14/C19–C21) of 34.6 (2)° in mol­ecule A and 29.65 (10)° in mol­ecule B, and is inclined to the piperidine ring mean plane (N1/C22–C26) by 15.69 (12)° in mol­ecule A and 12.36 (11)° in mol­ecule B. The mean planes of the pyran and piperidine rings are inclined to each other by 37.06 (11) and 29.49 (10)° in mol­ecules A and B, respectively. The mean plane of the pyrazine ring (N3/N4/C1/C2/C3/C4) makes a dihedral angle with the mean plane of the pyran ring (O2/C13/C14/C19–C21) of 63.42 (19)° in mol­ecule A and 72.64 (10)° in mol­ecule B. It is inclined to the pyrrolidine ring mean plane (N1/C12/C13/C21/C22) by 88.11 (1)° in mol­ecule A and 86.69 (11)° in mol­ecule B and is inclined to the piperidine ring mean plane (N1/C22–C26) by 77.24 (11)° in mol­ecule A and 82.97 (11)° in mol­ecule B.

3. Supra­molecular features

In the crystal, the B mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains propagating along the b-axis direction (Table 1[link] and Fig. 4[link]). The B mol­ecules are also linked by C—H⋯π inter­actions, and are linked to the A mol­ecules by C—H⋯π inter­actions (Table 1[link]). The result of these inter­molecular inter­actions is the formation of a supra­molecular three-dimensional structure (Table 1[link] and Fig. 4[link]).

[Figure 4]
Figure 4
The crystal packing of the title compound viewed along the c axis. The inter­linking of B mol­ecules via C—H⋯O hydrogen bonds (see Table 1[link] for details) generates chains running along the [010] direction. The A mol­ecules are shown in blue and the hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in the various inter­molecular inter­actions have been omitted.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.39, August 2018; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for the 6′-(4- phen­yl)-6a'-hexa­hydro-2H,6′H,6b' H-spiro­[benzo­pyrano[3,4-a]indolizin]-2-one skeleton yielded hits for two mol­ecules similar to the title compound: namely 6-(4-meth­oxy­phen­yl)-6a-nitro-6,6a,6 b,7,8,9,10,12a-octa­hydro­spiro­[chromeno[3,4-a]indolizine-12,3-indolin]-2-one (CSD refcode AFONEQ; Devi et al., 2013a[Devi, S. K., Srinivasan, T., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2013a). Acta Cryst. E69, o1047.]) and 6-(4-meth­oxy­phen­yl)-6a-nitro-6,6a,6 b,7,8,9,10,12a-octa­hydro­spiro­[chromeno[3,4-a]indolizine-12,3-indolin]-2-one (FIDCOM; Devi et al., 2013b[Devi, S. K., Srinivasan, T., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2013b). Acta Cryst. E69, o993.]). In both compounds, the piperidine ring has a chair conformation, as do the title compounds. In AFONEQ the pyran ring has a envelope conformation, as do molecules A and B of the title compounds, while in FIDCOM the pyran ring has a planar conformation. In these two compounds, the pyrrolidine ring adopts an envelope conformation as in mol­ecule A of the title compound. The bond lengths and bond angles are very similar to those reported here for the title compounds.

5. Synthesis and crystallization

To a solution of indeno­quinoxalinone (1.0 mmol) and pipacolinic acid (1.5 mmol) in dry toluene, was added 2-(4-chloro­phen­yl)-3-nitro-2H-chromene (1 mmol) under a nitro­gen atmosphere. The solution was refluxed for 20 h in a Dean–Stark apparatus to give the corresponding cyclo­adduct. After completion of the reaction, as indicated by TLC, the solvent was evaporated under reduced pressure. The crude product obtained was purified by column chromatography using hexa­ne/EtOAc (6:4) as eluent (yield 86%). Colourless block-like crystals of the title compound were obtained by slow evaporation of a solution in ethanol.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All H atoms were positioned geometrically and constrained to ride on their parent atoms: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C-meth­yl) and 1.2Ueq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula C35H27ClN4O3
Mr 587.05
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 14.1880 (1), 23.4450 (3), 18.3710 (2)
β (°) 104.541 (2)
V (Å3) 5915.14 (12)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.17
Crystal size (mm) 0.28 × 0.24 × 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.763, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections 47802, 11007, 6368
Rint 0.049
(sin θ/λ)max (Å−1) 0.606
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.128, 1.04
No. of reflections 11007
No. of parameters 824
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.35, −0.32
Computer programs: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS2018 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

In both mol­ecules, the nitro group oxygen atoms O3A and O4A in A and O3B and O4B in B are disordered over two positions with refined occupancy ratios of O3A/O4A:O3A′/O4A′ = 0.59 (2):0.41 (2), and O3B/O4B:O3B′/O4B′ = 0.686 (13):0.314 (13). In mol­ecule B, the chlorine atom Cl2 is disordered over two positions with a refined occupancy ratio of Cl2:Cl2′ = 0.72 (3):0.28 (3).

Supporting information

CCDC reference: 1024832

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989019000975/su5475sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019000975/su5475Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019000975/su5475Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

6-(4-Chlorophenyl)-6a-nitro-6a,6b,8,9,10,12a-hexahydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11'-indeno[1,2-b]quinoxaline] top
Crystal data top
C35H27ClN4O3F(000) = 2448
Mr = 587.05Dx = 1.318 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.1880 (1) ÅCell parameters from 14290 reflections
b = 23.4450 (3) Åθ = 1.4–28.3°
c = 18.3710 (2) ŵ = 0.17 mm−1
β = 104.541 (2)°T = 293 K
V = 5915.14 (12) Å3Block, colourless
Z = 80.28 × 0.24 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6368 reflections with I > 2σ(I)
ω and φ scansRint = 0.049
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		θmax = 25.5°, θmin = 1.4°
Tmin = 0.763, Tmax = 0.841h = −17→16
47802 measured reflectionsk = −28→28
11007 independent reflectionsl = −22→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0582P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.006
11007 reflectionsΔρmax = 0.35 e Å−3
824 parametersΔρmin = −0.32 e Å−3
0 restraintsExtinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00059 (14)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl1A−0.00824 (5)0.11344 (4)0.58679 (6)0.1082 (3)
O3A0.4634 (4)0.3265 (3)0.6462 (7)0.093 (3)0.59 (2)
O4A0.3489 (13)0.2767 (4)0.5822 (8)0.156 (5)0.59 (2)
O3A'0.4590 (5)0.2989 (9)0.5979 (10)0.109 (6)0.41 (2)
O4A'0.3204 (7)0.2772 (5)0.6066 (6)0.071 (3)0.41 (2)
O2A0.45596 (11)0.16374 (7)0.58900 (9)0.0664 (4)
N1A0.50758 (12)0.25630 (7)0.81689 (10)0.0495 (5)
N2A0.4135 (2)0.27834 (10)0.63100 (16)0.0724 (7)
N3A0.73468 (12)0.10164 (7)0.88894 (11)0.0546 (5)
N4A0.53615 (12)0.12159 (7)0.80912 (10)0.0479 (4)
C1A0.60146 (14)0.16158 (8)0.82389 (12)0.0441 (5)
C2A0.69943 (14)0.15201 (9)0.86567 (13)0.0491 (5)
C3A0.66770 (15)0.05800 (8)0.87139 (12)0.0473 (5)
C4A0.56935 (15)0.06792 (8)0.83442 (12)0.0464 (5)
C5A0.50372 (16)0.02191 (9)0.82077 (14)0.0580 (6)
H5A0.4383950.0281150.7973770.070*
C6A0.84079 (17)0.22040 (11)0.92049 (17)0.0791 (8)
H6A0.8839680.1920520.9434310.095*
C7A0.8676 (2)0.27716 (12)0.92813 (19)0.0902 (9)
H7A0.9291210.2872290.9568860.108*
C8A0.8040 (2)0.31873 (11)0.89352 (17)0.0792 (8)
H8A0.8228500.3567680.8997890.095*
C9A0.71276 (18)0.30543 (10)0.84969 (16)0.0698 (7)
H9A0.6707050.3339540.8257320.084*
C10A0.68507 (15)0.24874 (9)0.84208 (14)0.0541 (6)
C11A0.74920 (15)0.20657 (9)0.87840 (14)0.0556 (6)
C12A0.58742 (14)0.22441 (8)0.79981 (13)0.0475 (5)
C13A0.56278 (15)0.23380 (8)0.71304 (13)0.0501 (6)
H13A0.5810560.2732160.7052520.060*
C14A0.61130 (16)0.19680 (9)0.66583 (14)0.0555 (6)
C15A0.71259 (17)0.19720 (11)0.67750 (16)0.0753 (8)
H15A0.7506810.2178890.7173660.090*
C16A0.7565 (2)0.16720 (14)0.6304 (2)0.0964 (10)
H16A0.8239030.1673930.6389810.116*
C17A0.7008 (3)0.13700 (15)0.5708 (2)0.1035 (11)
H17A0.7307500.1172080.5388920.124*
C18A0.6011 (2)0.13591 (12)0.55817 (16)0.0837 (8)
H18A0.5634820.1154360.5178860.100*
C19A0.55733 (18)0.16564 (10)0.60611 (14)0.0623 (6)
C20A0.41794 (15)0.17284 (9)0.65322 (12)0.0528 (6)
H20A0.4496310.1444570.6905570.063*
C21A0.45075 (15)0.23143 (8)0.68847 (12)0.0484 (5)
C22A0.41783 (15)0.24203 (9)0.76128 (13)0.0488 (5)
H22A0.3946940.2055520.7762790.059*
C23A0.34060 (17)0.28633 (10)0.76270 (15)0.0691 (7)
H23A0.2797730.2757990.7276730.083*
H23B0.3606460.3231680.7478010.083*
C24A0.32669 (19)0.28976 (12)0.84187 (17)0.0853 (8)
H24A0.2821770.3206710.8443640.102*
H24B0.2974540.2545550.8532850.102*
C25A0.42135 (19)0.29947 (12)0.90013 (16)0.0799 (8)
H25A0.4098340.2975990.9499400.096*
H25B0.4457710.3372650.8935560.096*
C26A0.49693 (18)0.25542 (10)0.89383 (14)0.0655 (7)
H26A0.5586860.2642540.9288260.079*
H26B0.4764190.2178660.9058390.079*
C27A0.31104 (16)0.15833 (9)0.63324 (13)0.0540 (6)
C28A0.24932 (17)0.16813 (10)0.56282 (14)0.0660 (7)
H28A0.2739350.1836820.5248120.079*
C29A0.15004 (18)0.15474 (11)0.54862 (15)0.0733 (7)
H29A0.1085120.1618320.5016160.088*
C30A0.11461 (17)0.13090 (11)0.60519 (17)0.0694 (7)
C31A0.17473 (19)0.11935 (11)0.67385 (16)0.0712 (7)
H31A0.1502400.1027500.7112770.085*
C32A0.27203 (18)0.13245 (10)0.68733 (14)0.0639 (6)
H32A0.3130460.1237570.7340100.077*
C33A0.53600 (19)−0.03179 (10)0.84187 (15)0.0684 (7)
H33A0.492516−0.0621750.8319990.082*
C34A0.6328 (2)−0.04175 (10)0.87785 (15)0.0694 (7)
H34A0.653630−0.0786510.8919960.083*
C35A0.69781 (18)0.00240 (9)0.89266 (14)0.0611 (6)
H35A0.762530−0.0046460.9170740.073*
Cl2−0.4783 (4)−0.0038 (8)0.6049 (3)0.1272 (17)0.72 (3)
Cl2'−0.4841 (8)−0.0219 (5)0.6031 (6)0.075 (3)0.28 (3)
O2B−0.00811 (9)−0.04381 (5)0.61628 (8)0.0465 (4)
O3B0.0158 (3)−0.19290 (12)0.7246 (4)0.0803 (19)0.686 (13)
O4B−0.0989 (6)−0.1554 (3)0.6417 (4)0.0762 (18)0.686 (13)
O3B'0.0164 (6)−0.1739 (6)0.6662 (11)0.103 (7)0.314 (13)
O4B'−0.1267 (10)−0.1518 (7)0.6652 (10)0.085 (4)0.314 (13)
N1B0.05316 (11)−0.10204 (6)0.86520 (9)0.0425 (4)
N2B−0.03373 (16)−0.14979 (8)0.69290 (14)0.0569 (5)
N3B0.26320 (15)0.05649 (8)0.92353 (11)0.0627 (5)
N4B0.07324 (13)0.02914 (7)0.83140 (10)0.0499 (5)
C1B0.14136 (15)−0.00887 (8)0.85633 (11)0.0413 (5)
C2B0.23529 (15)0.00447 (9)0.90188 (12)0.0469 (5)
C3B0.1926 (2)0.09760 (9)0.89932 (15)0.0615 (7)
C4B0.09943 (19)0.08441 (9)0.85415 (13)0.0551 (6)
C5B0.0311 (2)0.12806 (10)0.82974 (15)0.0730 (8)
H5B−0.0301480.1196220.7991270.088*
C6B0.38409 (16)−0.05878 (12)0.96269 (14)0.0638 (7)
H6B0.424242−0.0288470.9846980.077*
C7B0.41665 (17)−0.11435 (13)0.97233 (15)0.0722 (7)
H7B0.479521−0.1219101.0006630.087*
C8B0.35666 (18)−0.15897 (11)0.94023 (15)0.0683 (7)
H8B0.379491−0.1962420.9476870.082*
C9B0.26356 (16)−0.14892 (9)0.89737 (13)0.0568 (6)
H9B0.223331−0.1790450.8761420.068*
C10B0.23102 (14)−0.09319 (8)0.88649 (12)0.0427 (5)
C11B0.29053 (14)−0.04826 (9)0.91966 (12)0.0468 (5)
C12B0.13200 (13)−0.07268 (7)0.84181 (11)0.0389 (5)
C13B0.10657 (13)−0.08981 (7)0.75708 (11)0.0376 (5)
H13B0.129220−0.1291820.7556380.045*
C14B0.14984 (14)−0.05683 (8)0.70283 (12)0.0400 (5)
C15B0.25031 (15)−0.05025 (9)0.71576 (13)0.0509 (5)
H15B0.290440−0.0611950.7618530.061*
C16B0.29121 (16)−0.02786 (10)0.66161 (14)0.0608 (6)
H16B0.358347−0.0233780.6713310.073*
C17B0.23213 (16)−0.01207 (10)0.59272 (14)0.0619 (6)
H17B0.2599230.0021970.5556860.074*
C18B0.13295 (15)−0.01723 (9)0.57845 (13)0.0530 (6)
H18B0.093362−0.0062870.5321490.064*
C19B0.09235 (14)−0.03897 (8)0.63384 (12)0.0414 (5)
C20B−0.04584 (14)−0.04205 (8)0.68166 (11)0.0417 (5)
H20B−0.018549−0.0076210.7092940.050*
C21B−0.00534 (13)−0.09262 (7)0.73357 (11)0.0388 (5)
C22B−0.03703 (13)−0.09156 (8)0.80785 (12)0.0427 (5)
H22B−0.057926−0.0525740.8150360.051*
C23B−0.11678 (15)−0.13179 (10)0.81870 (14)0.0601 (6)
H23C−0.177409−0.1232160.7821690.072*
H23D−0.099102−0.1709200.8112130.072*
C24B−0.12967 (17)−0.12448 (11)0.89788 (15)0.0712 (7)
H24C−0.156099−0.0869130.9027170.085*
H24D−0.175717−0.1525800.9067530.085*
C25B−0.03347 (16)−0.13142 (11)0.95634 (14)0.0666 (7)
H25C−0.042950−0.1235921.0058570.080*
H25D−0.011283−0.1705260.9558830.080*
C26B0.04359 (16)−0.09150 (9)0.94120 (13)0.0558 (6)
H26C0.024780−0.0521790.9460090.067*
H26D0.105333−0.0982770.9773210.067*
C27B−0.15509 (14)−0.03312 (9)0.65835 (12)0.0463 (5)
C28B−0.21425 (15)−0.05551 (9)0.59349 (13)0.0542 (6)
H28B−0.186285−0.0758480.5608080.065*
C29B−0.31419 (16)−0.04849 (11)0.57578 (14)0.0657 (7)
H29B−0.353288−0.0642740.5321080.079*
C30B−0.35442 (16)−0.01785 (12)0.62382 (15)0.0712 (8)
C31B−0.29829 (18)0.00675 (13)0.68675 (16)0.0824 (9)
H31B−0.3267000.0280810.7182700.099*
C32B−0.19809 (17)−0.00026 (10)0.70355 (14)0.0661 (7)
H32B−0.1592380.0174120.7458770.079*
C33B0.0553 (3)0.18321 (11)0.8514 (2)0.0940 (10)
H33B0.0103350.2122830.8350470.113*
C34B0.1459 (3)0.19590 (12)0.8972 (2)0.1033 (13)
H34B0.1605090.2335350.9116930.124*
C35B0.2144 (2)0.15477 (12)0.92177 (18)0.0885 (10)
H35B0.2748600.1642200.9529180.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0558 (4)0.1295 (7)0.1340 (8)−0.0009 (4)0.0141 (5)−0.0236 (6)
O3A0.090 (3)0.060 (3)0.125 (7)0.012 (2)0.019 (3)0.041 (3)
O4A0.211 (12)0.103 (4)0.096 (7)−0.009 (6)−0.069 (7)0.044 (5)
O3A'0.071 (4)0.138 (11)0.119 (10)0.007 (4)0.026 (5)0.083 (9)
O4A'0.050 (4)0.089 (4)0.068 (6)0.030 (3)0.000 (3)0.036 (4)
O2A0.0599 (10)0.0933 (12)0.0451 (10)0.0200 (9)0.0114 (8)−0.0011 (8)
N1A0.0466 (10)0.0523 (10)0.0482 (12)0.0092 (8)0.0096 (10)0.0035 (9)
N2A0.0817 (18)0.0717 (17)0.0695 (19)0.0311 (14)0.0297 (17)0.0288 (15)
N3A0.0496 (11)0.0496 (11)0.0604 (13)0.0099 (9)0.0060 (10)0.0068 (9)
N4A0.0468 (10)0.0476 (10)0.0464 (12)0.0015 (9)0.0064 (9)0.0083 (8)
C1A0.0420 (12)0.0467 (12)0.0429 (13)0.0046 (10)0.0092 (10)0.0060 (10)
C2A0.0415 (12)0.0505 (13)0.0524 (15)0.0045 (10)0.0064 (11)0.0051 (11)
C3A0.0532 (13)0.0447 (12)0.0432 (14)0.0050 (11)0.0110 (11)0.0024 (10)
C4A0.0538 (13)0.0448 (12)0.0400 (13)0.0053 (11)0.0105 (11)0.0045 (10)
C5A0.0574 (14)0.0490 (14)0.0625 (17)−0.0005 (11)0.0053 (12)0.0059 (11)
C6A0.0535 (16)0.0696 (17)0.103 (2)−0.0053 (13)−0.0017 (16)0.0133 (15)
C7A0.0613 (17)0.084 (2)0.111 (3)−0.0188 (16)−0.0050 (17)0.0029 (18)
C8A0.0722 (18)0.0607 (16)0.101 (2)−0.0163 (15)0.0157 (18)0.0041 (16)
C9A0.0645 (16)0.0510 (15)0.092 (2)−0.0031 (12)0.0161 (15)0.0096 (13)
C10A0.0499 (13)0.0484 (13)0.0635 (17)0.0002 (11)0.0131 (12)0.0048 (11)
C11A0.0445 (13)0.0564 (14)0.0624 (17)−0.0016 (11)0.0071 (12)0.0029 (12)
C12A0.0450 (12)0.0421 (12)0.0540 (15)0.0075 (10)0.0096 (11)0.0083 (10)
C13A0.0513 (13)0.0471 (12)0.0532 (15)0.0067 (10)0.0157 (12)0.0123 (10)
C14A0.0541 (14)0.0605 (14)0.0557 (17)0.0138 (11)0.0207 (13)0.0146 (12)
C15A0.0587 (16)0.0902 (18)0.085 (2)0.0135 (14)0.0327 (16)0.0109 (15)
C16A0.0688 (19)0.125 (3)0.106 (3)0.0219 (18)0.041 (2)−0.002 (2)
C17A0.097 (3)0.132 (3)0.098 (3)0.038 (2)0.055 (2)−0.003 (2)
C18A0.083 (2)0.107 (2)0.067 (2)0.0278 (16)0.0297 (17)−0.0042 (16)
C19A0.0624 (16)0.0752 (16)0.0528 (17)0.0194 (13)0.0207 (14)0.0121 (13)
C20A0.0532 (13)0.0664 (14)0.0379 (14)0.0171 (11)0.0100 (11)0.0078 (11)
C21A0.0503 (13)0.0488 (12)0.0462 (14)0.0164 (10)0.0124 (11)0.0151 (10)
C22A0.0491 (13)0.0487 (12)0.0490 (15)0.0058 (10)0.0133 (12)0.0044 (10)
C23A0.0566 (15)0.0798 (16)0.0704 (19)0.0256 (13)0.0151 (14)−0.0013 (14)
C24A0.0693 (18)0.111 (2)0.081 (2)0.0211 (16)0.0309 (17)−0.0120 (17)
C25A0.0826 (19)0.098 (2)0.0613 (19)0.0209 (16)0.0223 (16)−0.0129 (15)
C26A0.0728 (16)0.0730 (16)0.0498 (16)0.0088 (13)0.0139 (14)0.0032 (12)
C27A0.0527 (13)0.0606 (14)0.0439 (15)0.0150 (11)0.0036 (12)−0.0028 (11)
C28A0.0611 (16)0.0875 (18)0.0461 (16)0.0169 (13)0.0073 (13)0.0003 (13)
C29A0.0555 (16)0.102 (2)0.0532 (17)0.0227 (14)−0.0031 (14)−0.0085 (15)
C30A0.0519 (15)0.0826 (17)0.071 (2)0.0077 (13)0.0111 (15)−0.0173 (15)
C31A0.0637 (17)0.0844 (18)0.064 (2)−0.0125 (14)0.0140 (15)−0.0043 (14)
C32A0.0682 (17)0.0716 (16)0.0462 (16)−0.0012 (13)0.0036 (13)0.0050 (12)
C33A0.0770 (18)0.0504 (14)0.075 (2)−0.0092 (13)0.0149 (15)0.0022 (13)
C34A0.0859 (19)0.0449 (14)0.077 (2)0.0088 (14)0.0191 (16)0.0082 (13)
C35A0.0670 (15)0.0500 (14)0.0633 (17)0.0163 (12)0.0104 (13)0.0062 (12)
Cl20.0427 (12)0.233 (6)0.107 (2)0.020 (2)0.0209 (14)0.054 (2)
Cl2'0.034 (2)0.125 (6)0.069 (4)−0.001 (2)0.018 (2)−0.016 (5)
O2B0.0380 (8)0.0614 (9)0.0388 (9)−0.0054 (6)0.0073 (7)0.0037 (7)
O3B0.087 (2)0.0405 (17)0.096 (4)0.0010 (14)−0.010 (2)−0.0061 (18)
O4B0.090 (5)0.061 (2)0.056 (3)−0.010 (3)−0.023 (3)−0.011 (2)
O3B'0.065 (5)0.095 (7)0.158 (15)−0.025 (4)0.047 (6)−0.080 (9)
O4B'0.056 (6)0.077 (5)0.113 (11)−0.023 (4)0.005 (5)−0.039 (6)
N1B0.0381 (9)0.0496 (10)0.0382 (11)−0.0030 (8)0.0066 (8)0.0028 (8)
N2B0.0561 (13)0.0554 (13)0.0594 (16)−0.0195 (11)0.0150 (14)−0.0131 (12)
N3B0.0740 (13)0.0585 (12)0.0564 (14)−0.0248 (11)0.0179 (11)−0.0137 (10)
N4B0.0648 (12)0.0390 (10)0.0437 (11)0.0004 (9)0.0094 (9)−0.0022 (8)
C1B0.0486 (12)0.0422 (12)0.0322 (12)−0.0035 (10)0.0086 (10)−0.0009 (9)
C2B0.0516 (13)0.0487 (13)0.0407 (14)−0.0128 (11)0.0119 (11)−0.0033 (10)
C3B0.0920 (19)0.0442 (13)0.0571 (17)−0.0184 (14)0.0350 (15)−0.0052 (12)
C4B0.0858 (18)0.0403 (13)0.0433 (15)−0.0034 (13)0.0238 (14)0.0010 (10)
C5B0.109 (2)0.0484 (15)0.0691 (19)0.0136 (14)0.0356 (17)0.0049 (13)
C6B0.0423 (13)0.0922 (19)0.0542 (17)−0.0118 (13)0.0069 (12)−0.0103 (14)
C7B0.0450 (14)0.111 (2)0.0561 (18)0.0170 (15)0.0036 (13)0.0054 (16)
C8B0.0595 (16)0.0815 (18)0.0620 (18)0.0246 (14)0.0113 (14)0.0097 (14)
C9B0.0527 (14)0.0566 (14)0.0586 (16)0.0065 (11)0.0092 (13)0.0033 (11)
C10B0.0411 (11)0.0487 (12)0.0378 (13)0.0019 (10)0.0090 (10)0.0036 (10)
C11B0.0404 (12)0.0609 (14)0.0371 (13)−0.0075 (11)0.0060 (10)−0.0014 (10)
C12B0.0397 (11)0.0380 (11)0.0372 (13)−0.0016 (9)0.0062 (10)0.0001 (9)
C13B0.0385 (11)0.0347 (10)0.0381 (12)−0.0007 (8)0.0069 (10)−0.0025 (9)
C14B0.0400 (11)0.0401 (11)0.0406 (13)−0.0030 (9)0.0118 (10)−0.0039 (9)
C15B0.0413 (12)0.0654 (14)0.0447 (14)−0.0050 (10)0.0083 (11)−0.0023 (11)
C16B0.0409 (13)0.0850 (17)0.0582 (17)−0.0112 (12)0.0155 (13)−0.0006 (13)
C17B0.0555 (15)0.0802 (16)0.0545 (17)−0.0104 (13)0.0220 (13)0.0077 (13)
C18B0.0509 (13)0.0595 (13)0.0485 (15)−0.0051 (11)0.0123 (12)0.0068 (11)
C19B0.0384 (11)0.0416 (11)0.0444 (14)−0.0027 (9)0.0106 (11)−0.0015 (9)
C20B0.0398 (11)0.0465 (12)0.0368 (13)−0.0049 (9)0.0058 (10)−0.0025 (9)
C21B0.0391 (11)0.0366 (10)0.0383 (13)−0.0083 (9)0.0053 (10)−0.0067 (9)
C22B0.0399 (11)0.0457 (11)0.0417 (13)−0.0029 (9)0.0086 (10)0.0009 (9)
C23B0.0417 (12)0.0777 (16)0.0625 (17)−0.0116 (11)0.0160 (12)0.0107 (13)
C24B0.0505 (14)0.0999 (19)0.0679 (19)0.0002 (13)0.0235 (14)0.0182 (15)
C25B0.0590 (15)0.0902 (18)0.0534 (17)−0.0021 (13)0.0195 (13)0.0159 (13)
C26B0.0580 (14)0.0680 (14)0.0409 (14)0.0015 (12)0.0118 (12)0.0039 (11)
C27B0.0406 (12)0.0606 (13)0.0359 (13)0.0009 (10)0.0062 (11)0.0054 (11)
C28B0.0432 (13)0.0741 (15)0.0440 (15)−0.0028 (11)0.0083 (12)−0.0002 (12)
C29B0.0445 (13)0.0996 (19)0.0488 (16)−0.0106 (13)0.0039 (12)0.0070 (14)
C30B0.0362 (12)0.128 (2)0.0480 (17)0.0101 (14)0.0077 (13)0.0243 (16)
C31B0.0577 (16)0.141 (3)0.0496 (18)0.0362 (16)0.0158 (15)0.0031 (17)
C32B0.0585 (15)0.0905 (17)0.0443 (15)0.0173 (13)0.0036 (12)−0.0043 (13)
C33B0.151 (3)0.0446 (17)0.109 (3)0.0099 (18)0.074 (3)0.0111 (16)
C34B0.159 (3)0.0409 (17)0.140 (3)−0.022 (2)0.093 (3)−0.0154 (19)
C35B0.121 (2)0.0559 (17)0.103 (3)−0.0356 (17)0.055 (2)−0.0220 (16)
Geometric parameters (Å, º) top
Cl1A—C30A1.739 (2)Cl2'—C30B1.785 (11)
O3A—N2A1.325 (8)O2B—C19B1.385 (2)
O4A—N2A1.110 (9)O2B—C20B1.433 (2)
O3A'—N2A1.102 (7)O3B—N2B1.284 (4)
O4A'—N2A1.284 (12)O4B—N2B1.149 (6)
O2A—C19A1.394 (3)O3B'—N2B1.115 (7)
O2A—C20A1.431 (2)O4B'—N2B1.290 (15)
N1A—C12A1.456 (2)N1B—C26B1.457 (3)
N1A—C22A1.457 (3)N1B—C22B1.460 (2)
N1A—C26A1.459 (3)N1B—C12B1.467 (2)
N2A—C21A1.524 (3)N2B—C21B1.538 (3)
N3A—C2A1.312 (2)N3B—C2B1.313 (2)
N3A—C3A1.378 (3)N3B—C3B1.381 (3)
N4A—C1A1.298 (2)N4B—C1B1.310 (2)
N4A—C4A1.383 (2)N4B—C4B1.383 (3)
C1A—C2A1.427 (3)C1B—C2B1.419 (3)
C1A—C12A1.537 (3)C1B—C12B1.519 (3)
C2A—C11A1.451 (3)C2B—C11B1.456 (3)
C3A—C35A1.397 (3)C3B—C4B1.407 (3)
C3A—C4A1.409 (3)C3B—C35B1.414 (3)
C4A—C5A1.406 (3)C4B—C5B1.404 (3)
C5A—C33A1.362 (3)C5B—C33B1.371 (4)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C11A1.374 (3)C6B—C7B1.379 (3)
C6A—C7A1.382 (3)C6B—C11B1.386 (3)
C6A—H6A0.9300C6B—H6B0.9300
C7A—C8A1.372 (4)C7B—C8B1.384 (3)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.377 (3)C8B—C9B1.378 (3)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.383 (3)C9B—C10B1.383 (3)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.395 (3)C10B—C11B1.391 (3)
C10A—C12A1.519 (3)C10B—C12B1.517 (3)
C12A—C13A1.559 (3)C12B—C13B1.560 (3)
C13A—C14A1.509 (3)C13B—C14B1.508 (3)
C13A—C21A1.540 (3)C13B—C21B1.539 (2)
C13A—H13A0.9800C13B—H13B0.9800
C14A—C19A1.379 (3)C14B—C19B1.388 (3)
C14A—C15A1.399 (3)C14B—C15B1.394 (3)
C15A—C16A1.379 (4)C15B—C16B1.375 (3)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.374 (4)C16B—C17B1.382 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.375 (4)C17B—C18B1.370 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.387 (3)C18B—C19B1.386 (3)
C18A—H18A0.9300C18B—H18B0.9300
C20A—C27A1.507 (3)C20B—C27B1.515 (3)
C20A—C21A1.540 (3)C20B—C21B1.540 (3)
C20A—H20A0.9800C20B—H20B0.9800
C21A—C22A1.544 (3)C21B—C22B1.540 (3)
C22A—C23A1.515 (3)C22B—C23B1.524 (3)
C22A—H22A0.9800C22B—H22B0.9800
C23A—C24A1.518 (4)C23B—C24B1.521 (3)
C23A—H23A0.9700C23B—H23C0.9700
C23A—H23B0.9700C23B—H23D0.9700
C24A—C25A1.510 (4)C24B—C25B1.519 (3)
C24A—H24A0.9700C24B—H24C0.9700
C24A—H24B0.9700C24B—H24D0.9700
C25A—C26A1.514 (3)C25B—C26B1.517 (3)
C25A—H25A0.9700C25B—H25C0.9700
C25A—H25B0.9700C25B—H25D0.9700
C26A—H26A0.9700C26B—H26C0.9700
C26A—H26B0.9700C26B—H26D0.9700
C27A—C28A1.387 (3)C27B—C28B1.378 (3)
C27A—C32A1.392 (3)C27B—C32B1.382 (3)
C28A—C29A1.402 (3)C28B—C29B1.383 (3)
C28A—H28A0.9300C28B—H28B0.9300
C29A—C30A1.381 (4)C29B—C30B1.369 (3)
C29A—H29A0.9300C29B—H29B0.9300
C30A—C31A1.361 (4)C30B—C31B1.357 (4)
C31A—C32A1.375 (3)C31B—C32B1.387 (3)
C31A—H31A0.9300C31B—H31B0.9300
C32A—H32A0.9300C32B—H32B0.9300
C33A—C34A1.386 (3)C33B—C34B1.380 (5)
C33A—H33A0.9300C33B—H33B0.9300
C34A—C35A1.368 (3)C34B—C35B1.364 (4)
C34A—H34A0.9300C34B—H34B0.9300
C35A—H35A0.9300C35B—H35B0.9300
Cl2—C30B1.735 (5)
C19A—O2A—C20A112.99 (17)C26B—N1B—C22B112.79 (15)
C12A—N1A—C22A108.73 (16)C26B—N1B—C12B117.55 (16)
C12A—N1A—C26A118.50 (18)C22B—N1B—C12B107.72 (15)
C22A—N1A—C26A113.02 (17)O4B—N2B—O3B121.1 (4)
O3A'—N2A—O4A'120.6 (6)O3B'—N2B—O4B'120.7 (7)
O4A—N2A—O3A119.3 (6)O3B'—N2B—C21B122.5 (4)
O3A'—N2A—C21A123.2 (5)O4B—N2B—C21B123.8 (4)
O4A—N2A—C21A127.4 (6)O3B—N2B—C21B114.7 (2)
O4A'—N2A—C21A112.0 (5)O4B'—N2B—C21B109.9 (7)
O3A—N2A—C21A113.2 (4)C2B—N3B—C3B114.3 (2)
C2A—N3A—C3A114.08 (18)C1B—N4B—C4B114.39 (19)
C1A—N4A—C4A114.97 (17)N4B—C1B—C2B123.88 (18)
N4A—C1A—C2A123.15 (18)N4B—C1B—C12B125.74 (18)
N4A—C1A—C12A126.74 (18)C2B—C1B—C12B110.38 (17)
C2A—C1A—C12A110.11 (17)N3B—C2B—C1B123.4 (2)
N3A—C2A—C1A123.86 (19)N3B—C2B—C11B128.0 (2)
N3A—C2A—C11A127.6 (2)C1B—C2B—C11B108.55 (17)
C1A—C2A—C11A108.48 (18)N3B—C3B—C4B122.31 (19)
N3A—C3A—C35A118.9 (2)N3B—C3B—C35B118.7 (3)
N3A—C3A—C4A122.10 (18)C4B—C3B—C35B119.0 (3)
C35A—C3A—C4A119.0 (2)N4B—C4B—C5B118.3 (2)
N4A—C4A—C5A118.9 (2)N4B—C4B—C3B121.7 (2)
N4A—C4A—C3A121.64 (18)C5B—C4B—C3B120.0 (2)
C5A—C4A—C3A119.38 (19)C33B—C5B—C4B119.5 (3)
C33A—C5A—C4A119.9 (2)C33B—C5B—H5B120.2
C33A—C5A—H5A120.1C4B—C5B—H5B120.2
C4A—C5A—H5A120.1C7B—C6B—C11B118.9 (2)
C11A—C6A—C7A118.8 (2)C7B—C6B—H6B120.5
C11A—C6A—H6A120.6C11B—C6B—H6B120.5
C7A—C6A—H6A120.6C6B—C7B—C8B120.6 (2)
C8A—C7A—C6A120.3 (3)C6B—C7B—H7B119.7
C8A—C7A—H7A119.8C8B—C7B—H7B119.7
C6A—C7A—H7A119.8C9B—C8B—C7B120.9 (2)
C7A—C8A—C9A121.5 (2)C9B—C8B—H8B119.6
C7A—C8A—H8A119.2C7B—C8B—H8B119.6
C9A—C8A—H8A119.2C8B—C9B—C10B118.8 (2)
C8A—C9A—C10A118.5 (2)C8B—C9B—H9B120.6
C8A—C9A—H9A120.7C10B—C9B—H9B120.6
C10A—C9A—H9A120.7C9B—C10B—C11B120.5 (2)
C9A—C10A—C11A119.9 (2)C9B—C10B—C12B127.44 (19)
C9A—C10A—C12A127.7 (2)C11B—C10B—C12B112.01 (17)
C11A—C10A—C12A112.34 (18)C6B—C11B—C10B120.3 (2)
C6A—C11A—C10A120.9 (2)C6B—C11B—C2B131.6 (2)
C6A—C11A—C2A130.7 (2)C10B—C11B—C2B108.13 (18)
C10A—C11A—C2A108.37 (19)N1B—C12B—C10B111.32 (15)
N1A—C12A—C10A110.86 (17)N1B—C12B—C1B116.76 (15)
N1A—C12A—C1A118.80 (16)C10B—C12B—C1B100.89 (15)
C10A—C12A—C1A100.20 (16)N1B—C12B—C13B99.74 (14)
N1A—C12A—C13A99.27 (16)C10B—C12B—C13B114.16 (15)
C10A—C12A—C13A114.28 (17)C1B—C12B—C13B114.64 (15)
C1A—C12A—C13A114.15 (17)C14B—C13B—C21B113.52 (16)
C14A—C13A—C21A113.38 (19)C14B—C13B—C12B119.80 (15)
C14A—C13A—C12A119.26 (17)C21B—C13B—C12B104.77 (14)
C21A—C13A—C12A104.14 (16)C14B—C13B—H13B105.9
C14A—C13A—H13A106.4C21B—C13B—H13B105.9
C21A—C13A—H13A106.4C12B—C13B—H13B105.9
C12A—C13A—H13A106.4C19B—C14B—C15B117.62 (18)
C19A—C14A—C15A118.0 (2)C19B—C14B—C13B120.96 (17)
C19A—C14A—C13A121.3 (2)C15B—C14B—C13B120.84 (18)
C15A—C14A—C13A120.5 (2)C16B—C15B—C14B121.2 (2)
C16A—C15A—C14A120.6 (3)C16B—C15B—H15B119.4
C16A—C15A—H15A119.7C14B—C15B—H15B119.4
C14A—C15A—H15A119.7C15B—C16B—C17B119.7 (2)
C17A—C16A—C15A120.2 (3)C15B—C16B—H16B120.1
C17A—C16A—H16A119.9C17B—C16B—H16B120.1
C15A—C16A—H16A119.9C18B—C17B—C16B120.6 (2)
C18A—C17A—C16A120.3 (3)C18B—C17B—H17B119.7
C18A—C17A—H17A119.8C16B—C17B—H17B119.7
C16A—C17A—H17A119.8C17B—C18B—C19B119.2 (2)
C17A—C18A—C19A119.3 (3)C17B—C18B—H18B120.4
C17A—C18A—H18A120.3C19B—C18B—H18B120.4
C19A—C18A—H18A120.3O2B—C19B—C18B116.89 (19)
C14A—C19A—C18A121.6 (2)O2B—C19B—C14B121.49 (17)
C14A—C19A—O2A122.1 (2)C18B—C19B—C14B121.59 (18)
C18A—C19A—O2A116.3 (2)O2B—C20B—C27B109.76 (16)
O2A—C20A—C27A109.28 (18)O2B—C20B—C21B109.69 (14)
O2A—C20A—C21A110.05 (17)C27B—C20B—C21B118.53 (15)
C27A—C20A—C21A118.89 (17)O2B—C20B—H20B106.0
O2A—C20A—H20A105.9C27B—C20B—H20B106.0
C27A—C20A—H20A105.9C21B—C20B—H20B106.0
C21A—C20A—H20A105.9N2B—C21B—C13B107.44 (15)
N2A—C21A—C20A109.7 (2)N2B—C21B—C20B111.02 (17)
N2A—C21A—C13A109.26 (19)C13B—C21B—C20B109.83 (14)
C20A—C21A—C13A109.64 (16)N2B—C21B—C22B110.21 (15)
N2A—C21A—C22A110.86 (17)C13B—C21B—C22B105.12 (16)
C20A—C21A—C22A112.50 (16)C20B—C21B—C22B112.93 (15)
C13A—C21A—C22A104.76 (18)N1B—C22B—C23B110.28 (17)
N1A—C22A—C23A109.82 (18)N1B—C22B—C21B103.81 (14)
N1A—C22A—C21A104.07 (16)C23B—C22B—C21B119.82 (17)
C23A—C22A—C21A120.19 (18)N1B—C22B—H22B107.4
N1A—C22A—H22A107.4C23B—C22B—H22B107.4
C23A—C22A—H22A107.4C21B—C22B—H22B107.4
C21A—C22A—H22A107.4C24B—C23B—C22B109.08 (19)
C22A—C23A—C24A108.7 (2)C24B—C23B—H23C109.9
C22A—C23A—H23A109.9C22B—C23B—H23C109.9
C24A—C23A—H23A109.9C24B—C23B—H23D109.9
C22A—C23A—H23B109.9C22B—C23B—H23D109.9
C24A—C23A—H23B109.9H23C—C23B—H23D108.3
H23A—C23A—H23B108.3C25B—C24B—C23B111.20 (18)
C25A—C24A—C23A112.4 (2)C25B—C24B—H24C109.4
C25A—C24A—H24A109.1C23B—C24B—H24C109.4
C23A—C24A—H24A109.1C25B—C24B—H24D109.4
C25A—C24A—H24B109.1C23B—C24B—H24D109.4
C23A—C24A—H24B109.1H24C—C24B—H24D108.0
H24A—C24A—H24B107.9C26B—C25B—C24B111.43 (19)
C24A—C25A—C26A111.3 (2)C26B—C25B—H25C109.3
C24A—C25A—H25A109.4C24B—C25B—H25C109.3
C26A—C25A—H25A109.4C26B—C25B—H25D109.3
C24A—C25A—H25B109.4C24B—C25B—H25D109.3
C26A—C25A—H25B109.4H25C—C25B—H25D108.0
H25A—C25A—H25B108.0N1B—C26B—C25B108.41 (18)
N1A—C26A—C25A108.2 (2)N1B—C26B—H26C110.0
N1A—C26A—H26A110.1C25B—C26B—H26C110.0
C25A—C26A—H26A110.1N1B—C26B—H26D110.0
N1A—C26A—H26B110.1C25B—C26B—H26D110.0
C25A—C26A—H26B110.1H26C—C26B—H26D108.4
H26A—C26A—H26B108.4C28B—C27B—C32B117.8 (2)
C28A—C27A—C32A117.8 (2)C28B—C27B—C20B123.35 (18)
C28A—C27A—C20A123.4 (2)C32B—C27B—C20B118.8 (2)
C32A—C27A—C20A118.7 (2)C27B—C28B—C29B121.6 (2)
C27A—C28A—C29A120.4 (2)C27B—C28B—H28B119.2
C27A—C28A—H28A119.8C29B—C28B—H28B119.2
C29A—C28A—H28A119.8C30B—C29B—C28B118.7 (2)
C30A—C29A—C28A119.3 (2)C30B—C29B—H29B120.7
C30A—C29A—H29A120.4C28B—C29B—H29B120.7
C28A—C29A—H29A120.4C31B—C30B—C29B121.5 (2)
C31A—C30A—C29A121.1 (2)C31B—C30B—Cl2116.0 (5)
C31A—C30A—Cl1A119.8 (2)C29B—C30B—Cl2122.4 (4)
C29A—C30A—Cl1A119.0 (2)C31B—C30B—Cl2'123.9 (3)
C30A—C31A—C32A119.3 (2)C29B—C30B—Cl2'114.1 (3)
C30A—C31A—H31A120.3C30B—C31B—C32B119.3 (2)
C32A—C31A—H31A120.3C30B—C31B—H31B120.4
C31A—C32A—C27A122.0 (2)C32B—C31B—H31B120.4
C31A—C32A—H32A119.0C27B—C32B—C31B121.0 (2)
C27A—C32A—H32A119.0C27B—C32B—H32B119.5
C5A—C33A—C34A120.9 (2)C31B—C32B—H32B119.5
C5A—C33A—H33A119.6C5B—C33B—C34B120.5 (3)
C34A—C33A—H33A119.6C5B—C33B—H33B119.8
C35A—C34A—C33A120.4 (2)C34B—C33B—H33B119.8
C35A—C34A—H34A119.8C35B—C34B—C33B121.8 (3)
C33A—C34A—H34A119.8C35B—C34B—H34B119.1
C34A—C35A—C3A120.5 (2)C33B—C34B—H34B119.1
C34A—C35A—H35A119.8C34B—C35B—C3B119.2 (3)
C3A—C35A—H35A119.8C34B—C35B—H35B120.4
C19B—O2B—C20B112.44 (15)C3B—C35B—H35B120.4
C4A—N4A—C1A—C2A−2.5 (3)C4B—N4B—C1B—C12B178.48 (17)
C4A—N4A—C1A—C12A176.95 (19)C3B—N3B—C2B—C1B1.1 (3)
C3A—N3A—C2A—C1A−1.8 (3)C3B—N3B—C2B—C11B−177.9 (2)
C3A—N3A—C2A—C11A176.6 (2)N4B—C1B—C2B—N3B0.0 (3)
N4A—C1A—C2A—N3A4.6 (3)C12B—C1B—C2B—N3B−179.61 (18)
C12A—C1A—C2A—N3A−174.9 (2)N4B—C1B—C2B—C11B179.10 (18)
N4A—C1A—C2A—C11A−174.02 (19)C12B—C1B—C2B—C11B−0.5 (2)
C12A—C1A—C2A—C11A6.5 (2)C2B—N3B—C3B—C4B−1.1 (3)
C2A—N3A—C3A—C35A179.2 (2)C2B—N3B—C3B—C35B177.9 (2)
C2A—N3A—C3A—C4A−2.5 (3)C1B—N4B—C4B—C5B179.66 (19)
C1A—N4A—C4A—C5A−179.82 (19)C1B—N4B—C4B—C3B1.0 (3)
C1A—N4A—C4A—C3A−1.8 (3)N3B—C3B—C4B—N4B0.1 (3)
N3A—C3A—C4A—N4A4.5 (3)C35B—C3B—C4B—N4B−179.0 (2)
C35A—C3A—C4A—N4A−177.15 (19)N3B—C3B—C4B—C5B−178.6 (2)
N3A—C3A—C4A—C5A−177.5 (2)C35B—C3B—C4B—C5B2.4 (3)
C35A—C3A—C4A—C5A0.9 (3)N4B—C4B—C5B—C33B−179.9 (2)
N4A—C4A—C5A—C33A176.7 (2)C3B—C4B—C5B—C33B−1.2 (3)
C3A—C4A—C5A—C33A−1.4 (3)C11B—C6B—C7B—C8B−0.6 (4)
C11A—C6A—C7A—C8A−0.7 (5)C6B—C7B—C8B—C9B0.7 (4)
C6A—C7A—C8A—C9A−0.9 (5)C7B—C8B—C9B—C10B0.4 (3)
C7A—C8A—C9A—C10A1.2 (4)C8B—C9B—C10B—C11B−1.4 (3)
C8A—C9A—C10A—C11A−0.1 (4)C8B—C9B—C10B—C12B−179.9 (2)
C8A—C9A—C10A—C12A177.1 (2)C7B—C6B—C11B—C10B−0.4 (3)
C7A—C6A—C11A—C10A1.8 (4)C7B—C6B—C11B—C2B177.4 (2)
C7A—C6A—C11A—C2A−174.7 (3)C9B—C10B—C11B—C6B1.4 (3)
C9A—C10A—C11A—C6A−1.5 (4)C12B—C10B—C11B—C6B−179.87 (19)
C12A—C10A—C11A—C6A−179.1 (2)C9B—C10B—C11B—C2B−176.84 (18)
C9A—C10A—C11A—C2A175.7 (2)C12B—C10B—C11B—C2B1.8 (2)
C12A—C10A—C11A—C2A−1.9 (3)N3B—C2B—C11B—C6B0.2 (4)
N3A—C2A—C11A—C6A−4.6 (4)C1B—C2B—C11B—C6B−178.9 (2)
C1A—C2A—C11A—C6A173.9 (3)N3B—C2B—C11B—C10B178.2 (2)
N3A—C2A—C11A—C10A178.6 (2)C1B—C2B—C11B—C10B−0.8 (2)
C1A—C2A—C11A—C10A−2.9 (3)C26B—N1B—C12B—C10B66.0 (2)
C22A—N1A—C12A—C10A164.91 (17)C22B—N1B—C12B—C10B−165.34 (15)
C26A—N1A—C12A—C10A−64.2 (2)C26B—N1B—C12B—C1B−49.1 (2)
C22A—N1A—C12A—C1A−79.9 (2)C22B—N1B—C12B—C1B79.6 (2)
C26A—N1A—C12A—C1A51.0 (3)C26B—N1B—C12B—C13B−173.19 (16)
C22A—N1A—C12A—C13A44.37 (19)C22B—N1B—C12B—C13B−44.49 (17)
C26A—N1A—C12A—C13A175.23 (18)C9B—C10B—C12B—N1B52.0 (3)
C9A—C10A—C12A—N1A−45.7 (3)C11B—C10B—C12B—N1B−126.56 (17)
C11A—C10A—C12A—N1A131.70 (19)C9B—C10B—C12B—C1B176.56 (19)
C9A—C10A—C12A—C1A−172.0 (2)C11B—C10B—C12B—C1B−2.0 (2)
C11A—C10A—C12A—C1A5.4 (2)C9B—C10B—C12B—C13B−60.0 (3)
C9A—C10A—C12A—C13A65.5 (3)C11B—C10B—C12B—C13B121.47 (18)
C11A—C10A—C12A—C13A−117.1 (2)N4B—C1B—C12B—N1B−57.3 (3)
N4A—C1A—C12A—N1A52.7 (3)C2B—C1B—C12B—N1B122.22 (18)
C2A—C1A—C12A—N1A−127.8 (2)N4B—C1B—C12B—C10B−178.12 (18)
N4A—C1A—C12A—C10A173.5 (2)C2B—C1B—C12B—C10B1.4 (2)
C2A—C1A—C12A—C10A−7.0 (2)N4B—C1B—C12B—C13B58.7 (2)
N4A—C1A—C12A—C13A−63.9 (3)C2B—C1B—C12B—C13B−121.69 (18)
C2A—C1A—C12A—C13A115.5 (2)N1B—C12B—C13B—C14B162.78 (16)
N1A—C12A—C13A—C14A−165.11 (18)C10B—C12B—C13B—C14B−78.4 (2)
C10A—C12A—C13A—C14A76.9 (2)C1B—C12B—C13B—C14B37.2 (2)
C1A—C12A—C13A—C14A−37.7 (3)N1B—C12B—C13B—C21B33.99 (17)
N1A—C12A—C13A—C21A−37.50 (18)C10B—C12B—C13B—C21B152.76 (15)
C10A—C12A—C13A—C21A−155.51 (16)C1B—C12B—C13B—C21B−91.55 (17)
C1A—C12A—C13A—C21A89.96 (19)C21B—C13B—C14B—C19B−8.9 (2)
C21A—C13A—C14A—C19A1.3 (3)C12B—C13B—C14B—C19B−133.61 (18)
C12A—C13A—C14A—C19A124.5 (2)C21B—C13B—C14B—C15B−179.94 (17)
C21A—C13A—C14A—C15A175.57 (19)C12B—C13B—C14B—C15B55.3 (2)
C12A—C13A—C14A—C15A−61.2 (3)C19B—C14B—C15B—C16B−1.2 (3)
C19A—C14A—C15A—C16A0.0 (4)C13B—C14B—C15B—C16B170.14 (19)
C13A—C14A—C15A—C16A−174.5 (2)C14B—C15B—C16B—C17B−0.7 (3)
C14A—C15A—C16A—C17A0.7 (5)C15B—C16B—C17B—C18B1.6 (4)
C15A—C16A—C17A—C18A−0.8 (5)C16B—C17B—C18B—C19B−0.5 (3)
C16A—C17A—C18A—C19A0.1 (5)C20B—O2B—C19B—C18B−154.42 (17)
C15A—C14A—C19A—C18A−0.7 (4)C20B—O2B—C19B—C14B27.7 (2)
C13A—C14A—C19A—C18A173.8 (2)C17B—C18B—C19B—O2B−179.39 (18)
C15A—C14A—C19A—O2A−178.5 (2)C17B—C18B—C19B—C14B−1.5 (3)
C13A—C14A—C19A—O2A−4.1 (3)C15B—C14B—C19B—O2B−179.88 (17)
C17A—C18A—C19A—C14A0.6 (4)C13B—C14B—C19B—O2B8.8 (3)
C17A—C18A—C19A—O2A178.6 (2)C15B—C14B—C19B—C18B2.3 (3)
C20A—O2A—C19A—C14A−27.2 (3)C13B—C14B—C19B—C18B−169.04 (18)
C20A—O2A—C19A—C18A154.9 (2)C19B—O2B—C20B—C27B166.38 (15)
C19A—O2A—C20A—C27A−168.56 (18)C19B—O2B—C20B—C21B−61.74 (19)
C19A—O2A—C20A—C21A59.2 (2)O3B'—N2B—C21B—C13B−22.4 (14)
O3A'—N2A—C21A—C20A−99.6 (17)O4B—N2B—C21B—C13B−142.6 (5)
O4A—N2A—C21A—C20A25.4 (15)O3B—N2B—C21B—C13B43.6 (4)
O4A'—N2A—C21A—C20A57.6 (6)O4B'—N2B—C21B—C13B−173.4 (9)
O3A—N2A—C21A—C20A−158.5 (6)O3B'—N2B—C21B—C20B97.7 (14)
O3A'—N2A—C21A—C13A20.6 (17)O4B—N2B—C21B—C20B−22.4 (6)
O4A—N2A—C21A—C13A145.6 (15)O3B—N2B—C21B—C20B163.7 (4)
O4A'—N2A—C21A—C13A177.8 (6)O4B'—N2B—C21B—C20B−53.3 (9)
O3A—N2A—C21A—C13A−38.3 (6)O3B'—N2B—C21B—C22B−136.4 (14)
O3A'—N2A—C21A—C22A135.6 (17)O4B—N2B—C21B—C22B103.4 (6)
O4A—N2A—C21A—C22A−99.4 (15)O3B—N2B—C21B—C22B−70.4 (4)
O4A'—N2A—C21A—C22A−67.2 (6)O4B'—N2B—C21B—C22B72.5 (9)
O3A—N2A—C21A—C22A76.7 (6)C14B—C13B—C21B—N2B96.99 (19)
O2A—C20A—C21A—N2A60.0 (2)C12B—C13B—C21B—N2B−130.54 (16)
C27A—C20A—C21A—N2A−67.0 (2)C14B—C13B—C21B—C20B−23.9 (2)
O2A—C20A—C21A—C13A−59.9 (2)C12B—C13B—C21B—C20B108.61 (16)
C27A—C20A—C21A—C13A172.98 (18)C14B—C13B—C21B—C22B−145.63 (15)
O2A—C20A—C21A—C22A−176.09 (16)C12B—C13B—C21B—C22B−13.16 (18)
C27A—C20A—C21A—C22A56.8 (3)O2B—C20B—C21B—N2B−59.52 (19)
C14A—C13A—C21A—N2A−91.0 (2)C27B—C20B—C21B—N2B67.6 (2)
C12A—C13A—C21A—N2A137.88 (18)O2B—C20B—C21B—C13B59.2 (2)
C14A—C13A—C21A—C20A29.2 (2)C27B—C20B—C21B—C13B−173.75 (16)
C12A—C13A—C21A—C20A−101.90 (18)O2B—C20B—C21B—C22B176.12 (14)
C14A—C13A—C21A—C22A150.20 (17)C27B—C20B—C21B—C22B−56.8 (2)
C12A—C13A—C21A—C22A19.04 (19)C26B—N1B—C22B—C23B−62.0 (2)
C12A—N1A—C22A—C23A−163.08 (17)C12B—N1B—C22B—C23B166.59 (16)
C26A—N1A—C22A—C23A63.2 (2)C26B—N1B—C22B—C21B168.41 (15)
C12A—N1A—C22A—C21A−33.18 (19)C12B—N1B—C22B—C21B37.05 (18)
C26A—N1A—C22A—C21A−166.94 (16)N2B—C21B—C22B—N1B102.47 (18)
N2A—C21A—C22A—N1A−110.9 (2)C13B—C21B—C22B—N1B−13.01 (18)
C20A—C21A—C22A—N1A125.88 (17)C20B—C21B—C22B—N1B−132.74 (16)
C13A—C21A—C22A—N1A6.84 (19)N2B—C21B—C22B—C23B−21.0 (3)
N2A—C21A—C22A—C23A12.5 (3)C13B—C21B—C22B—C23B−136.53 (18)
C20A—C21A—C22A—C23A−110.7 (2)C20B—C21B—C22B—C23B103.8 (2)
C13A—C21A—C22A—C23A130.2 (2)N1B—C22B—C23B—C24B56.4 (2)
N1A—C22A—C23A—C24A−56.5 (3)C21B—C22B—C23B—C24B176.73 (18)
C21A—C22A—C23A—C24A−177.1 (2)C22B—C23B—C24B—C25B−53.5 (3)
C22A—C23A—C24A—C25A53.1 (3)C23B—C24B—C25B—C26B54.6 (3)
C23A—C24A—C25A—C26A−53.5 (3)C22B—N1B—C26B—C25B60.7 (2)
C12A—N1A—C26A—C25A170.03 (19)C12B—N1B—C26B—C25B−173.01 (17)
C22A—N1A—C26A—C25A−61.1 (2)C24B—C25B—C26B—N1B−56.2 (3)
C24A—C25A—C26A—N1A54.9 (3)O2B—C20B—C27B—C28B34.6 (3)
O2A—C20A—C27A—C28A−35.0 (3)C21B—C20B—C27B—C28B−92.5 (2)
C21A—C20A—C27A—C28A92.5 (3)O2B—C20B—C27B—C32B−144.46 (19)
O2A—C20A—C27A—C32A143.4 (2)C21B—C20B—C27B—C32B88.5 (2)
C21A—C20A—C27A—C32A−89.2 (3)C32B—C27B—C28B—C29B−3.8 (3)
C32A—C27A—C28A—C29A3.1 (3)C20B—C27B—C28B—C29B177.15 (19)
C20A—C27A—C28A—C29A−178.6 (2)C27B—C28B—C29B—C30B0.8 (3)
C27A—C28A—C29A—C30A−0.9 (4)C28B—C29B—C30B—C31B1.8 (4)
C28A—C29A—C30A—C31A−1.2 (4)C28B—C29B—C30B—Cl2177.0 (6)
C28A—C29A—C30A—Cl1A−179.08 (18)C28B—C29B—C30B—Cl2'−170.1 (5)
C29A—C30A—C31A—C32A1.0 (4)C29B—C30B—C31B—C32B−1.3 (4)
Cl1A—C30A—C31A—C32A178.90 (18)Cl2—C30B—C31B—C32B−176.9 (6)
C30A—C31A—C32A—C27A1.3 (4)Cl2'—C30B—C31B—C32B169.7 (6)
C28A—C27A—C32A—C31A−3.3 (3)C28B—C27B—C32B—C31B4.2 (3)
C20A—C27A—C32A—C31A178.3 (2)C20B—C27B—C32B—C31B−176.6 (2)
C4A—C5A—C33A—C34A1.0 (4)C30B—C31B—C32B—C27B−1.8 (4)
C5A—C33A—C34A—C35A−0.2 (4)C4B—C5B—C33B—C34B−0.4 (4)
C33A—C34A—C35A—C3A−0.4 (4)C5B—C33B—C34B—C35B0.8 (5)
N3A—C3A—C35A—C34A178.4 (2)C33B—C34B—C35B—C3B0.5 (4)
C4A—C3A—C35A—C34A0.0 (3)N3B—C3B—C35B—C34B178.9 (2)
C4B—N4B—C1B—C2B−1.0 (3)C4B—C3B—C35B—C34B−2.0 (4)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of rings C14B–C19B, C3B–C5B/C33B–C35B and C3A–C5A/C33A–C35A, respectively.
D—H···AD—HH···AD···AD—H···A
C20A—H20A···N4A0.982.283.170 (3)151
C20B—H20B···N4B0.982.453.298 (3)144
C33B—H33B···O3Bi0.932.463.271 (5)145
C8A—H8A···Cg1ii0.932.693.536 (3)151
C25B—H25C···Cg2iii0.972.733.629 (3)155
C31B—H31B···Cg3iv0.932.993.742 (3)139
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, −y, −z+2; (iv) x−1, y, z.
 

Acknowledgements

The authors are thankful to the SAIF, IIT Madras, for the data collection.

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ISSN: 2056-9890
Volume 75| Part 2| February 2019| Pages 255-259
https://doi.org/10.1107/S2056989019000975
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