research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 73| Part 2| February 2017| Pages 137-140
https://doi.org/10.1107/S2056989016020612

Crystal structure of (E)-N1-[(anthracen-9-yl)methyl­­idene]-N4-phenyl­benzene-1,4-di­amine

CROSSMARK_Color_square_no_text.svg
Md. Serajul Haque Faizi,a Ashanul Haque,a Musheer Ahmadb and Irina A. Golenyac*

aDepartment of Chemistry, College of Science, Sultan Qaboos University, PO Box 36 Al-Khod 123, Muscat, Sultanate of Oman, bDepartment of Applied Chemistry, Aligarh Muslim University 202 002 UP , India, and cNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine
*Correspondence e-mail: igolenya@ua.fm

Edited by G. Smith, Queensland University of Technology, Australia (Received 12 December 2016; accepted 28 December 2016; online 10 January 2017)

The title compound, C27H20N2, a Schiff base synthesized via a condensation reaction between anthracene-9-carbaldehyde and N-phenyl-p-phenyl­enedi­amine, crystallizes with three independent mol­ecules in the asymmetric unit. The three mol­ecules have slightly varying overall conformations, all having trans conformations with respect to the C=N bond. In the crystal, the packing features N—H⋯N hydrogen bonds, which connect mol­ecules into chains extending along the c-axis direction, inter­linked by C—H⋯π inter­actions (minimum H⋯Cg = 2.65 Å) into sheets lying parallel to (001).

CCDC reference: 1524849

Similar articles

1. Chemical context

Anthracene derivatives have been widely used in the field of anion recognition, metal ion fluorescent sensors, as well as pH sensors (Gunnlaugsson et al., 2003[Gunnlaugsson, T., Lee, T. C. & Parkesh, R. (2003). Org. Lett. 5, 4065-4068.]; Chen & Chen, 2004[Chen, Q. Y. & Chen, C. F. (2004). Tetrahedron Lett. 45, 6493-6496.]; Kim & Yoon, 2002[Kim, S. K. & Yoon, J. (2002). Chem. Commun. pp. 770-771.]; Bernhardt et al. 2001[Bernhardt, P. V., Moore, E. G. & Riley, M. J. (2001). Inorg. Chem. 40, 5799-5805.]) because of their excellent photophysical properties and high fluorescence. The crystal structures of several anthracene derivatives have been reported previously for supra­molecular photochemistry (Akiba et al., 1999[Akiba, K., Yamashita, M., Yamamoto, Y. & Nagase, S. (1999). J. Am. Chem. Soc. 121, 10644-10645.]; Yuan et al., 2004[Yuan, W.-B., Yan, L. & Yang, R.-D. (2004). Acta Cryst. E60, o2447-o2448.]; Yamashita et al., 2005[Yamashita, M., Yamamoto, Y., Akiba, K., Hashizume, D., Iwasaki, F., Takagi, N. & Nagase, S. (2005). J. Am. Chem. Soc. 127, 4354-4371.]). As part of our ongoing studies of Schiff bases (Faizi et al., 2016[Faizi, M. S. H., Gupta, S., Mohan, V. K., Jain, K. V. & Sen, P. (2016). Sens. Actuators B Chem. 222, 15-20.]), we report herein on the synthesis and crystal structure of the title compound, (E)-N1-[(anthracen-9-yl)methyl­idene]-N4-phenyl­benzene-1,4-di­amine, obtained from the condensation of 9-anthracenecarboxaldehyde with N-phenyl-p-phenyl­enedi­amine.

[Scheme 1]

2. Structural commentary

The title compound, crystallizes with three independent mol­ecules (A, B and C) in the asymmetric unit (Fig. 1[link]). Mol­ecules B and C are linked by an N—H ⋯N hydrogen bond and a C—H⋯π inter­action, while mol­ecule A forms a C—H⋯π inter­action with mol­ecule B, as well as an N—H⋯N hydrogen bond and a C—H⋯π inter­action with a symmetry-generated A mol­ecule. An intra­molecular C—H⋯N hydrogen bond occurs in each mol­ecule (Table 1[link]). There is a slight variation (within 3σ) in the bond lengths and angles of the three independent mol­ecules. All three mol­ecules have trans conformations. The central C=N (C15—N1) bond lengths are 1.277 (2), 1.276 (2) and 1.271 (2) Å for mol­ecules A, B and C, respectively. These are close to the literature value of 1.279 Å for Csp2=Nsp2 bonds (Fritsky et al., 2004[Fritsky, I. O., Świątek-Kozłowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.]; Penkova et al., 2010[Penkova, L., Demeshko, S., Pavlenko, V. A., Dechert, S., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 3036-3040.]). The C14—C15 bond lengths between the anthracene moiety and the central C=N bond in A, B and C are 1.474 (3), 1.472 (3) and 1.476 (3) Å, respectively. The comparative N1—C16 bonds connecting the central benzene ring to the central C=N bond in A, B and C are 1.422 (2), 1.419 (2) and 1.420 (2) Å, respectively. The C14—C15—N1—C16, torsion angles for the –C—C—N—C– bridge groups are −178.47 (17)° (for A), −176.35 (17)° (for B) and 178.31 (17)° (for C). The comparative dihedral angles between the anthracene ring system of the mol­ecule (defined by C1–C14) and the benzene and phenyl rings (defined by C16–C21 and C22–C27) and between the benzene and phenyl rings, respectively, are 82.68 (4), 73.76 (5) and 25.63 (11)° in A, 80.10 (4), 78.82 (5) and 22.56 (11)° (in B) and 85.02 (5), 81.66 (5) and 16.25 (11)° (in C).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4, Cg10,Cg11, Cg12, Cg13,Cg18, Cg20 and Cg21are the centroids of the C1A–C14A, C16A–C21A, C1B–C14B, C8B–C13B, C16B–C21B, C22B–C27B, C1C–C14C, C22C–C27C and C1C–C8Crings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C12A—H9A⋯N1A 0.93 2.44 2.989 (3) 118
C12B—H9B⋯N1B 0.93 2.47 3.006 (3) 117
C2C—H1C⋯N1C 0.93 2.51 3.032 (3) 116
N2A—H20A⋯N1Ai 0.92 (2) 2.28 (2) 3.147 (2) 158.4 (18)
N2B—H20B⋯N1Cii 0.88 (2) 2.19 (2) 3.056 (2) 166.2 (19)
N2C—H20C⋯N1B 0.90 (2) 2.22 (2) 3.094 (2) 163.2 (17)
C2A—H1A⋯Cg13iii 0.93 2.93 3.7248 (3) 144
C2B—H1B⋯Cg21iv 0.93 2.91 3.6227 (3) 134
C4A—H3A⋯Cg21v 0.93 2.75 3.6728 (3) 175
C10A—H7A⋯Cg12ii 0.93 2.80 3.5075 (3) 134
C17A—H11A⋯Cg18ii 0.93 2.65 3.5119 (3) 154
C17B—H11B⋯Cg10v 0.93 2.79 3.6243 (3) 150
C17B—H11B⋯Cg11v 0.93 2.89 3.7248 (3) 150
C21C—H13C⋯Cg2vi 0.93 2.86 3.7513 (3) 162
C23A—H15A⋯Cg2i 0.93 2.85 3.7253 (3) 157
C23B—H15B⋯Cg18ii 0.93 2.87 3.7057 (3) 149
C25A—H17A⋯Cg20vii 0.93 2.96 3.6262 (3) 130
C25B—H17B⋯Cg4viii 0.93 3.00 3.6476 (3) 128
C25C—H17C⋯Cg12iv 0.93 2.84 3.6263 (3) 143
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z+1; (iii) x-1, y, z-1; (iv) -x+2, -y+1, -z+1; (v) -x+1, -y+1, -z+1; (vi) x, y, z-1; (vii) [x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (viii) x+1, y, z.
[Figure 1]
Figure 1
A view of the three independent mol­ecules (A, B and C) in the asymmetric unit of the title compound with the atom-labelling scheme and 40% probability displacement ellipsoids, showing the C—H⋯N inter­action between molecules B and C as a dashed line.

3. Supra­molecular features

In the crystal, the mol­ecules are connected by N—H⋯N hydrogen bonds that result in separate –A–A–A–A– and –B–C–B–C– chains, which both propagate in [001] (Table 1[link] and Fig. 2[link]). The chains are linked via C—H⋯π inter­actions between the phenyl and central benzene rings and those of the anthracene moiety groups of neighbouring mol­ecules [minimum C17A—H⋯Cg(C1C–C14C) = 2.65 Å; C—H⋯Cg = 154°], forming layers lying parallel to (001) (Fig. 3[link], Table 1[link]).

[Figure 2]
Figure 2
A view of the hydrogen-bonded chains propagating in [001]. Hydrogen bonds are shown as dashed lines; see Table 1[link] for details.
[Figure 3]
Figure 3
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (Version 5.36; last update November 2014; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) gave three hits for Schiff base compounds involving N-phenyl-p-phenyl­enedi­amine. Of these three compounds, N1-phenyl-N-4-(quinolin-2-yl­methyl­ene)benzene-1,4-di­amine {synonym: N-phenyl-4-[(quinolin-2-yl­methyl­ene)amino]-aniline; WOJJIQ (Faizi et al., 2014[Faizi, M. S. H., Mashrai, A., Garandal, S. & Shahid, M. (2014). Acta Cryst. E70, o905-o906.]] is the most similar to the title compound, with dihedral angles between quinoline ring system (r.m.s. deviation = 0.027 Å) and the central benzene and terminal phenyl rings of 44.72 (7) and 9.02 (4)°, respectively. Another similar structure crystal is that of N1-phenyl-N4-[(E)-(pyren-1-yl)-methyl­idene]benzene-1,4-di­amine (Faizi & Prisyazhnaya, 2015[Faizi, M. S. H. & Prisyazhnaya, E. V. (2015). Acta Cryst. E71, 261-263.]), which has dihedral angles between the pyrenyl ring system (r.m.s. deviation = 0.027 Å) and the central and terminal benzene rings of 43.43 (9) and 29.33 (7)°, respectively. Some similar ligands have been used as dual chemosensors for the detection of Cu2+and Hg2+ ions (Udhayakumari & Velmathi, 2015[Udhayakumari, D. & Velmathi, S. (2015). Ind. Eng. Chem. Res. 54, 3541-3547.]) but their crystal structures have not been reported.

5. Synthesis and crystallization

80 mg (0.435 mmol) of N-phenyl-p-phenyl­enedi­amine were dissolved in 10 ml of absolute ethanol. To this solution, 89 mg (0.434 mmol) of 9-anthracenecarboxaldehyde in 5 ml of absolute ethanol was added dropwise under stirring. The mixture was stirred for 10 min, two drops of glacial acetic acid were then added and the mixture was further refluxed for 2h. The resulting yellow precipitate was recovered by filtration, washed several times with small portions of ice-cold ethanol and then with diethyl ether to give 140 mg (87%) of the title compound. Dark-yellow block-like crystals suitable for X-ray analysis were obtained within 3 days by slow evaporation of a solution in MeOH.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The N-bound H atoms were located in a difference Fourier map. Their positional and isotropic thermal parameters were included in further stages of the refinement. All C-bound H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and with Uiso(H)= 1.2–1.5Ueq(C).

Table 2
Experimental details

Crystal data
Chemical formula C27H20N2
Mr 372.45
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 11.1554 (8), 45.224 (3), 11.5856 (8)
β (°) 96.645 (2)
V (Å3) 5805.5 (7)
Z 12
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.20 × 0.15 × 0.10
 
Data collection
Diffractometer BRUKER SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.944, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections 70261, 10276, 6957
Rint 0.066
(sin θ/λ)max (Å−1) 0.596
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.121, 1.04
No. of reflections 10276
No. of parameters 796
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.18, −0.28
Computer programs: SMART and SAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and DIAMOND (Brandenberg & Putz, 2006[Brandenberg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).

Supporting information

CCDC reference: 1524849

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989016020612/zs2373sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016020612/zs2373Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016020612/zs2373Isup3.cml

checkCIF report


Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenberg & Putz, 2006); software used to prepare material for publication: DIAMOND (Brandenberg & Putz, 2006).

(E)-N1-[(Anthracen-9-yl)methylidene]-N4-phenylbenzene-1,4-diamine top
Crystal data top
C27H20N2F(000) = 2352
Mr = 372.45Dx = 1.278 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.1554 (8) ÅCell parameters from 9870 reflections
b = 45.224 (3) Åθ = 2.7–27.3°
c = 11.5856 (8) ŵ = 0.08 mm−1
β = 96.645 (2)°T = 100 K
V = 5805.5 (7) Å3Block, yellow
Z = 120.20 × 0.15 × 0.10 mm
Data collection top
BRUKER SMART APEX CCD
diffractometer		10276 independent reflections
Radiation source: fine-focus sealed tube6957 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		h = −13→13
Tmin = 0.944, Tmax = 0.981k = −53→53
70261 measured reflectionsl = −13→13
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0468P)2 + 1.868P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
10276 reflectionsΔρmax = 0.18 e Å−3
796 parametersΔρmin = −0.28 e Å−3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.26112 (17)0.61937 (4)1.02008 (17)0.0262 (5)
C1B0.71492 (18)0.45788 (4)0.46717 (17)0.0282 (5)
C1C0.55519 (18)0.68363 (4)−0.18917 (18)0.0314 (5)
C2A0.18402 (18)0.62145 (5)0.91327 (17)0.0313 (5)
H1A0.17130.63980.87760.038*
C2B0.78872 (19)0.45822 (4)0.57631 (18)0.0327 (5)
H1B0.79290.47530.62110.039*
C2C0.49613 (18)0.65789 (5)−0.23828 (18)0.0357 (5)
H1C0.50330.6402−0.19710.043*
C3A0.12888 (19)0.59724 (5)0.86268 (19)0.0352 (5)
H2A0.07980.59930.79250.042*
C3B0.8530 (2)0.43405 (5)0.61612 (19)0.0393 (6)
H2B0.89940.43480.68810.047*
C3C0.4297 (2)0.65861 (6)−0.34359 (19)0.0442 (6)
H2C0.39310.6413−0.37370.053*
C4A0.14451 (19)0.56901 (5)0.9145 (2)0.0380 (6)
H3A0.10770.55250.87790.046*
C4B0.8504 (2)0.40788 (5)0.5497 (2)0.0418 (6)
H3B0.89480.39150.57790.050*
C4C0.4149 (2)0.68491 (6)−0.4086 (2)0.0503 (7)
H3C0.36870.6850−0.48080.060*
C5A0.21301 (19)0.56617 (5)1.0172 (2)0.0375 (6)
H4A0.22150.54761.05190.045*
C5B0.7831 (2)0.40671 (5)0.4451 (2)0.0385 (6)
H4B0.78230.38940.40170.046*
C5C0.4680 (2)0.71001 (6)−0.3653 (2)0.0474 (7)
H4C0.45760.7274−0.40830.057*
C6A0.27303 (18)0.59094 (4)1.07454 (18)0.0309 (5)
C6B0.71353 (18)0.43128 (4)0.39983 (18)0.0303 (5)
C6C0.53946 (19)0.71046 (5)−0.25565 (19)0.0366 (6)
C7A0.33961 (19)0.58833 (5)1.18216 (19)0.0351 (5)
H5A0.34490.56991.21810.042*
C7B0.64679 (18)0.43032 (4)0.29127 (18)0.0331 (5)
H5B0.64680.41300.24810.040*
C7C0.5933 (2)0.73624 (5)−0.2093 (2)0.0435 (6)
H5C0.58370.7535−0.25280.052*
C8A0.39895 (18)0.61213 (5)1.23881 (18)0.0318 (5)
C8B0.57997 (18)0.45425 (4)0.24448 (17)0.0298 (5)
C8C0.6606 (2)0.73722 (5)−0.1012 (2)0.0392 (6)
C9A0.4676 (2)0.60887 (5)1.34924 (19)0.0416 (6)
H6A0.47070.59051.38580.050*
C9B0.5082 (2)0.45245 (5)0.13519 (18)0.0382 (6)
H6B0.50860.43510.09220.046*
C9C0.7169 (2)0.76360 (5)−0.0555 (3)0.0531 (7)
H6C0.70560.7810−0.09830.064*
C10A0.5281 (2)0.63167 (6)1.4019 (2)0.0467 (6)
H7A0.57230.62911.47430.056*
C10B0.4397 (2)0.47522 (5)0.09266 (19)0.0431 (6)
H7B0.39300.47360.02110.052*
C10C0.7862 (3)0.76430 (5)0.0479 (3)0.0566 (8)
H7C0.82090.78200.07600.068*
C11A0.52493 (19)0.65969 (5)1.34739 (19)0.0428 (6)
H8A0.56860.67531.38380.051*
C11B0.4388 (2)0.50170 (5)0.15699 (19)0.0408 (6)
H8B0.39040.51730.12750.049*
C11C0.8057 (2)0.73793 (5)0.1131 (2)0.0501 (7)
H8C0.85430.73830.18390.060*
C12A0.45909 (18)0.66419 (5)1.24274 (18)0.0339 (5)
H9A0.45790.68281.20880.041*
C12B0.50720 (18)0.50484 (5)0.26098 (18)0.0314 (5)
H9B0.50580.52270.30090.038*
C12C0.7541 (2)0.71209 (5)0.07366 (19)0.0409 (6)
H9C0.76880.69500.11770.049*
C13A0.39169 (17)0.64070 (4)1.18408 (17)0.0271 (5)
C13B0.58098 (17)0.48128 (4)0.30983 (17)0.0266 (5)
C13C0.67808 (19)0.71060 (4)−0.03370 (18)0.0328 (5)
C14A0.32106 (17)0.64399 (4)1.07609 (16)0.0252 (5)
C14B0.65076 (17)0.48293 (4)0.41958 (17)0.0249 (5)
C14C0.62503 (18)0.68413 (4)−0.07964 (18)0.0298 (5)
C15A0.30094 (17)0.67319 (4)1.02085 (17)0.0262 (5)
H10A0.30430.67480.94120.031*
C15B0.66532 (17)0.51095 (4)0.48428 (16)0.0248 (5)
H10B0.65770.51110.56340.030*
C15C0.65310 (18)0.65659 (4)−0.01366 (17)0.0275 (5)
H10C0.64070.65570.06430.033*
C16A0.25826 (17)0.72330 (4)1.01442 (16)0.0233 (4)
C16B0.70840 (16)0.56121 (4)0.50147 (15)0.0211 (4)
C16C0.72269 (17)0.60827 (4)0.00646 (15)0.0215 (4)
C17A0.32184 (17)0.73145 (4)0.92280 (16)0.0244 (4)
H11A0.38540.71970.90410.029*
C17B0.65393 (16)0.56740 (4)0.60083 (15)0.0225 (4)
H11B0.59460.55480.62270.027*
C17C0.82786 (18)0.59356 (4)−0.00799 (16)0.0267 (5)
H11C0.87430.5999−0.06490.032*
C18A0.29143 (17)0.75671 (4)0.85951 (16)0.0240 (4)
H12A0.33510.76190.79880.029*
C18B0.68698 (16)0.59196 (4)0.66704 (16)0.0226 (4)
H12B0.64980.59560.73340.027*
C18C0.86612 (17)0.56949 (4)0.06038 (16)0.0266 (5)
H12C0.93960.56060.05150.032*
C19A0.19624 (17)0.77470 (4)0.88491 (16)0.0220 (4)
C19B0.77522 (16)0.61147 (4)0.63675 (15)0.0210 (4)
C19C0.79554 (17)0.55846 (4)0.14235 (15)0.0211 (4)
C20A0.13906 (18)0.76750 (4)0.98216 (16)0.0289 (5)
H13A0.07910.77981.00450.035*
C20B0.82151 (18)0.60648 (4)0.53181 (16)0.0287 (5)
H13B0.87530.62000.50580.034*
C20C0.68619 (17)0.57274 (4)0.15263 (16)0.0231 (4)
H14C0.63620.56550.20500.028*
C21A0.17071 (18)0.74221 (4)1.04569 (16)0.0287 (5)
H14A0.13220.73791.11070.034*
C21B0.78838 (18)0.58171 (4)0.46604 (16)0.0278 (5)
H14B0.82060.57880.39640.033*
C21C0.65063 (17)0.59727 (4)0.08713 (15)0.0236 (4)
H13C0.57810.60660.09680.028*
C22A0.06858 (17)0.81786 (4)0.80373 (16)0.0238 (4)
C22B0.90242 (17)0.65480 (4)0.71494 (16)0.0238 (4)
C22C0.92058 (17)0.51468 (4)0.22658 (16)0.0235 (4)
C23A0.0768 (2)0.84370 (5)0.74049 (19)0.0386 (6)
H15A0.14850.84800.71030.046*
C23B0.8996 (2)0.67904 (5)0.78831 (19)0.0408 (6)
H15B0.83390.68160.82980.049*
C23C1.00215 (18)0.51024 (4)0.14642 (18)0.0321 (5)
H15C0.99700.52170.07950.038*
C24A−0.0180 (2)0.86307 (5)0.7212 (2)0.0432 (6)
H16A−0.01010.88000.67730.052*
C24B0.9923 (2)0.69923 (5)0.8007 (2)0.0508 (7)
H16B0.98840.71520.85060.061*
C24C1.09106 (19)0.48884 (4)0.16520 (18)0.0346 (5)
H16C1.14600.48650.11130.042*
C25A−0.1242 (2)0.85767 (5)0.76608 (18)0.0357 (5)
H17A−0.18830.87090.75430.043*
C25B1.0897 (2)0.69612 (5)0.7408 (2)0.0461 (6)
H17B1.15160.71000.74830.055*
C25C1.09985 (19)0.47100 (5)0.26146 (19)0.0375 (6)
H17C1.15850.45630.27210.045*
C26A−0.1336 (2)0.83227 (5)0.8286 (2)0.0419 (6)
H18A−0.20510.82840.85990.050*
C26B1.0947 (2)0.67210 (5)0.66918 (19)0.0427 (6)
H18B1.16110.66970.62840.051*
C26C1.0197 (2)0.47527 (5)0.34235 (19)0.0402 (6)
H18C1.02460.46340.40840.048*
C27A−0.03963 (19)0.81222 (5)0.84664 (18)0.0361 (5)
H19A−0.04930.79490.88780.043*
C27B1.00284 (18)0.65145 (5)0.65651 (18)0.0331 (5)
H19B1.00860.63520.60840.040*
C27C0.93266 (19)0.49686 (4)0.32602 (17)0.0332 (5)
H19C0.88070.49970.38230.040*
N1A0.27915 (14)0.69645 (3)1.07744 (13)0.0248 (4)
N1B0.68818 (13)0.53510 (3)0.43417 (13)0.0230 (4)
N1C0.69395 (14)0.63399 (3)−0.06137 (13)0.0248 (4)
N2A0.16966 (15)0.79942 (3)0.81534 (14)0.0268 (4)
N2B0.80552 (15)0.63521 (4)0.70989 (14)0.0263 (4)
N2C0.82550 (15)0.53481 (3)0.21699 (14)0.0254 (4)
H20A0.2198 (19)0.8020 (5)0.7589 (19)0.044 (7)*
H20B0.7628 (19)0.6364 (4)0.7690 (18)0.038 (6)*
H20C0.7737 (17)0.5329 (4)0.2703 (17)0.027 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0274 (11)0.0251 (11)0.0284 (11)0.0057 (9)0.0130 (9)0.0017 (9)
C1B0.0298 (12)0.0254 (11)0.0321 (12)−0.0082 (9)0.0153 (10)0.0008 (9)
C1C0.0297 (12)0.0325 (12)0.0349 (12)0.0139 (10)0.0156 (10)0.0094 (10)
C2A0.0385 (13)0.0282 (12)0.0285 (12)0.0030 (10)0.0092 (10)0.0019 (9)
C2B0.0411 (13)0.0237 (11)0.0346 (13)−0.0042 (10)0.0094 (11)0.0004 (10)
C2C0.0297 (12)0.0417 (14)0.0367 (13)0.0101 (10)0.0078 (10)0.0099 (11)
C3A0.0375 (13)0.0336 (13)0.0356 (12)−0.0017 (10)0.0092 (10)−0.0045 (10)
C3B0.0458 (14)0.0340 (13)0.0391 (13)−0.0011 (11)0.0088 (11)0.0055 (11)
C3C0.0318 (13)0.0597 (16)0.0409 (14)0.0071 (12)0.0027 (11)0.0084 (12)
C4A0.0332 (12)0.0330 (13)0.0493 (15)−0.0052 (10)0.0112 (12)−0.0053 (11)
C4B0.0422 (14)0.0296 (13)0.0554 (16)0.0042 (11)0.0137 (13)0.0075 (12)
C4C0.0355 (14)0.076 (2)0.0398 (14)0.0160 (14)0.0055 (11)0.0158 (14)
C5A0.0339 (12)0.0231 (12)0.0579 (16)−0.0005 (10)0.0161 (12)0.0050 (11)
C5B0.0386 (13)0.0252 (12)0.0544 (16)−0.0025 (10)0.0162 (12)−0.0051 (11)
C5C0.0414 (14)0.0595 (17)0.0442 (15)0.0261 (13)0.0170 (12)0.0282 (13)
C6A0.0268 (11)0.0275 (12)0.0409 (13)0.0077 (9)0.0147 (10)0.0067 (10)
C6B0.0304 (11)0.0252 (12)0.0381 (13)−0.0060 (10)0.0159 (10)−0.0042 (10)
C6C0.0348 (13)0.0364 (13)0.0422 (14)0.0162 (11)0.0202 (11)0.0156 (11)
C7A0.0334 (12)0.0289 (12)0.0459 (14)0.0082 (10)0.0174 (11)0.0130 (11)
C7B0.0344 (12)0.0258 (12)0.0426 (14)−0.0098 (10)0.0189 (11)−0.0139 (10)
C7C0.0447 (14)0.0351 (14)0.0564 (16)0.0174 (11)0.0299 (13)0.0252 (12)
C8A0.0259 (11)0.0403 (13)0.0312 (12)0.0144 (10)0.0112 (10)0.0121 (10)
C8B0.0273 (11)0.0320 (12)0.0330 (12)−0.0104 (10)0.0157 (10)−0.0080 (10)
C8C0.0429 (14)0.0253 (12)0.0550 (16)0.0077 (10)0.0289 (12)0.0088 (11)
C9A0.0387 (14)0.0470 (15)0.0396 (14)0.0156 (12)0.0062 (11)0.0124 (12)
C9B0.0378 (13)0.0424 (14)0.0358 (13)−0.0136 (11)0.0104 (11)−0.0163 (11)
C9C0.0625 (18)0.0279 (14)0.076 (2)0.0044 (12)0.0374 (16)0.0078 (13)
C10A0.0365 (14)0.0704 (18)0.0319 (13)0.0195 (13)−0.0019 (11)0.0107 (13)
C10B0.0377 (14)0.0572 (17)0.0332 (13)−0.0104 (12)−0.0005 (11)−0.0129 (12)
C10C0.0690 (19)0.0333 (15)0.075 (2)−0.0108 (13)0.0412 (17)−0.0121 (14)
C11A0.0284 (12)0.0577 (16)0.0413 (14)0.0047 (11)0.0002 (11)−0.0017 (12)
C11B0.0360 (13)0.0451 (14)0.0399 (14)−0.0018 (11)−0.0014 (11)−0.0065 (11)
C11C0.0623 (17)0.0406 (15)0.0514 (15)−0.0098 (13)0.0243 (13)−0.0112 (13)
C12A0.0272 (12)0.0412 (13)0.0334 (12)0.0077 (10)0.0035 (10)0.0021 (10)
C12B0.0301 (12)0.0309 (12)0.0336 (12)−0.0051 (10)0.0059 (10)−0.0052 (10)
C12C0.0547 (15)0.0297 (13)0.0417 (14)−0.0007 (11)0.0202 (12)−0.0016 (11)
C13A0.0231 (11)0.0324 (12)0.0275 (11)0.0084 (9)0.0096 (9)0.0021 (9)
C13B0.0259 (11)0.0271 (11)0.0290 (11)−0.0100 (9)0.0126 (9)−0.0046 (9)
C13C0.0407 (13)0.0239 (12)0.0384 (13)0.0075 (10)0.0233 (11)0.0019 (10)
C14A0.0260 (11)0.0261 (11)0.0253 (11)0.0069 (9)0.0101 (9)0.0038 (9)
C14B0.0263 (11)0.0231 (11)0.0275 (11)−0.0068 (9)0.0121 (9)−0.0031 (9)
C14C0.0347 (12)0.0252 (12)0.0326 (12)0.0094 (10)0.0170 (10)0.0044 (9)
C15A0.0286 (11)0.0272 (11)0.0237 (11)0.0017 (9)0.0071 (9)0.0014 (9)
C15B0.0280 (11)0.0264 (11)0.0212 (10)−0.0021 (9)0.0078 (9)−0.0015 (9)
C15C0.0351 (12)0.0258 (11)0.0230 (11)0.0029 (9)0.0094 (9)0.0024 (9)
C16A0.0278 (11)0.0212 (10)0.0204 (10)0.0001 (9)0.0014 (9)−0.0015 (8)
C16B0.0227 (10)0.0203 (10)0.0194 (10)0.0003 (8)−0.0013 (8)0.0010 (8)
C16C0.0282 (11)0.0198 (10)0.0165 (10)0.0005 (9)0.0020 (9)−0.0005 (8)
C17A0.0242 (11)0.0233 (11)0.0260 (11)0.0022 (9)0.0038 (9)−0.0020 (9)
C17B0.0214 (10)0.0212 (11)0.0251 (11)−0.0020 (8)0.0041 (9)0.0037 (9)
C17C0.0326 (12)0.0253 (11)0.0242 (11)0.0017 (9)0.0116 (9)0.0044 (9)
C18A0.0269 (11)0.0243 (11)0.0216 (10)−0.0027 (9)0.0057 (9)−0.0017 (9)
C18B0.0250 (11)0.0233 (11)0.0207 (10)0.0022 (9)0.0080 (9)−0.0004 (8)
C18C0.0248 (11)0.0257 (11)0.0307 (11)0.0045 (9)0.0096 (9)0.0027 (9)
C19A0.0252 (11)0.0199 (10)0.0200 (10)−0.0020 (9)−0.0006 (8)−0.0027 (8)
C19B0.0233 (11)0.0191 (10)0.0202 (10)0.0005 (8)0.0011 (8)0.0010 (8)
C19C0.0263 (11)0.0191 (10)0.0173 (10)−0.0021 (8)0.0001 (8)−0.0016 (8)
C20A0.0327 (12)0.0291 (12)0.0265 (11)0.0082 (9)0.0095 (10)−0.0006 (9)
C20B0.0328 (12)0.0292 (12)0.0256 (11)−0.0125 (10)0.0102 (9)−0.0023 (9)
C20C0.0273 (11)0.0222 (10)0.0207 (10)−0.0016 (9)0.0075 (9)−0.0011 (8)
C21A0.0359 (12)0.0312 (12)0.0205 (11)0.0055 (10)0.0093 (9)0.0022 (9)
C21B0.0358 (12)0.0300 (12)0.0192 (10)−0.0062 (10)0.0097 (9)−0.0027 (9)
C21C0.0229 (10)0.0247 (11)0.0235 (10)0.0041 (9)0.0040 (9)−0.0010 (9)
C22A0.0287 (11)0.0238 (11)0.0186 (10)0.0020 (9)0.0016 (9)−0.0018 (8)
C22B0.0271 (11)0.0214 (11)0.0218 (10)−0.0026 (9)−0.0012 (9)0.0021 (9)
C22C0.0246 (11)0.0207 (10)0.0248 (11)−0.0021 (9)0.0009 (9)−0.0019 (9)
C23A0.0405 (14)0.0350 (13)0.0420 (14)0.0050 (11)0.0122 (11)0.0127 (11)
C23B0.0465 (14)0.0348 (13)0.0421 (14)−0.0084 (11)0.0092 (11)−0.0112 (11)
C23C0.0387 (13)0.0277 (12)0.0308 (12)0.0060 (10)0.0085 (10)0.0028 (10)
C24A0.0505 (15)0.0333 (13)0.0451 (14)0.0077 (12)0.0029 (12)0.0119 (11)
C24B0.0685 (18)0.0318 (14)0.0498 (16)−0.0171 (13)−0.0022 (14)−0.0102 (12)
C24C0.0323 (12)0.0340 (13)0.0380 (13)0.0055 (10)0.0058 (10)−0.0069 (11)
C25A0.0377 (13)0.0317 (13)0.0351 (13)0.0123 (10)−0.0074 (11)−0.0046 (10)
C25B0.0501 (16)0.0398 (14)0.0436 (14)−0.0243 (12)−0.0147 (13)0.0132 (12)
C25C0.0334 (13)0.0348 (13)0.0416 (14)0.0108 (10)−0.0068 (11)−0.0041 (11)
C26A0.0298 (12)0.0488 (15)0.0480 (15)0.0075 (11)0.0080 (11)0.0059 (12)
C26B0.0314 (13)0.0545 (16)0.0411 (14)−0.0125 (12)−0.0004 (11)0.0079 (12)
C26C0.0433 (14)0.0365 (13)0.0390 (13)0.0102 (11)−0.0030 (11)0.0096 (11)
C27A0.0333 (12)0.0334 (13)0.0423 (13)0.0032 (10)0.0071 (11)0.0139 (10)
C27B0.0290 (12)0.0363 (13)0.0334 (12)−0.0065 (10)0.0014 (10)−0.0030 (10)
C27C0.0341 (12)0.0347 (12)0.0312 (12)0.0025 (10)0.0063 (10)0.0052 (10)
N1A0.0264 (9)0.0244 (9)0.0239 (9)0.0050 (7)0.0041 (7)0.0008 (8)
N1B0.0236 (9)0.0229 (9)0.0228 (9)−0.0041 (7)0.0042 (7)−0.0015 (7)
N1C0.0283 (9)0.0237 (9)0.0229 (9)0.0037 (8)0.0055 (7)0.0018 (7)
N2A0.0292 (10)0.0254 (10)0.0271 (9)0.0047 (8)0.0088 (8)0.0032 (8)
N2B0.0287 (10)0.0262 (10)0.0251 (9)−0.0058 (8)0.0085 (8)−0.0062 (8)
N2C0.0287 (10)0.0248 (9)0.0243 (9)0.0044 (8)0.0093 (8)0.0051 (8)
Geometric parameters (Å, º) top
C1A—C14A1.417 (3)C15B—N1B1.276 (2)
C1A—C2A1.426 (3)C15B—H10B0.9300
C1A—C6A1.432 (3)C15C—N1C1.271 (2)
C1B—C14B1.417 (3)C15C—H10C0.9300
C1B—C2B1.427 (3)C16A—C21A1.378 (3)
C1B—C6B1.433 (3)C16A—C17A1.393 (3)
C1C—C14C1.410 (3)C16A—N1A1.422 (2)
C1C—C2C1.423 (3)C16B—C21B1.381 (3)
C1C—C6C1.437 (3)C16B—C17B1.391 (2)
C2A—C3A1.355 (3)C16B—N1B1.419 (2)
C2A—H1A0.9300C16C—C17C1.376 (3)
C2B—C3B1.359 (3)C16C—C21C1.393 (3)
C2B—H1B0.9300C16C—N1C1.420 (2)
C2C—C3C1.352 (3)C17A—C18A1.379 (3)
C2C—H1C0.9300C17A—H11A0.9300
C3A—C4A1.413 (3)C17B—C18B1.375 (2)
C3A—H2A0.9300C17B—H11B0.9300
C3B—C4B1.410 (3)C17C—C18C1.384 (3)
C3B—H2B0.9300C17C—H11C0.9300
C3C—C4C1.407 (3)C18A—C19A1.396 (3)
C3C—H2C0.9300C18A—H12A0.9300
C4A—C5A1.344 (3)C18B—C19B1.397 (3)
C4A—H3A0.9300C18B—H12B0.9300
C4B—C5B1.351 (3)C18C—C19C1.394 (3)
C4B—H3B0.9300C18C—H12C0.9300
C4C—C5C1.350 (3)C19A—N2A1.390 (2)
C4C—H3C0.9300C19A—C20A1.396 (3)
C5A—C6A1.429 (3)C19B—N2B1.385 (2)
C5A—H4A0.9300C19B—C20B1.393 (3)
C5B—C6B1.420 (3)C19C—N2C1.392 (2)
C5B—H4B0.9300C19C—C20C1.397 (3)
C5C—C6C1.419 (3)C20A—C21A1.383 (3)
C5C—H4C0.9300C20A—H13A0.9300
C6A—C7A1.381 (3)C20B—C21B1.381 (3)
C6B—C7B1.386 (3)C20B—H13B0.9300
C6C—C7C1.390 (3)C20C—C21C1.376 (2)
C7A—C8A1.388 (3)C20C—H14C0.9300
C7A—H5A0.9300C21A—H14A0.9300
C7B—C8B1.388 (3)C21B—H14B0.9300
C7B—H5B0.9300C21C—H13C0.9300
C7C—C8C1.385 (3)C22A—C27A1.381 (3)
C7C—H5C0.9300C22A—C23A1.388 (3)
C8A—C9A1.421 (3)C22A—N2A1.396 (2)
C8A—C13A1.437 (3)C22B—C27B1.383 (3)
C8B—C9B1.420 (3)C22B—C23B1.390 (3)
C8B—C13B1.437 (3)C22B—N2B1.394 (2)
C8C—C9C1.422 (3)C22C—C23C1.388 (3)
C8C—C13C1.436 (3)C22C—N2C1.392 (2)
C9A—C10A1.340 (3)C22C—C27C1.400 (3)
C9A—H6A0.9300C23A—C24A1.371 (3)
C9B—C10B1.341 (3)C23A—H15A0.9300
C9B—H6B0.9300C23B—C24B1.374 (3)
C9C—C10C1.349 (4)C23B—H15B0.9300
C9C—H6C0.9300C23C—C24C1.385 (3)
C10A—C11A1.414 (3)C23C—H15C0.9300
C10A—H7A0.9300C24A—C25A1.370 (3)
C10B—C11B1.411 (3)C24A—H16A0.9300
C10B—H7B0.9300C24B—C25B1.363 (3)
C10C—C11C1.415 (3)C24B—H16B0.9300
C10C—H7C0.9300C24C—C25C1.371 (3)
C11A—C12A1.358 (3)C24C—H16C0.9300
C11A—H8A0.9300C25A—C26A1.369 (3)
C11B—C12B1.357 (3)C25A—H17A0.9300
C11B—H8B0.9300C25B—C26B1.372 (3)
C11C—C12C1.358 (3)C25B—H17B0.9300
C11C—H8C0.9300C25C—C26C1.382 (3)
C12A—C13A1.428 (3)C25C—H17C0.9300
C12A—H9A0.9300C26A—C27A1.384 (3)
C12B—C13B1.423 (3)C26A—H18A0.9300
C12B—H9B0.9300C26B—C27B1.382 (3)
C12C—C13C1.424 (3)C26B—H18B0.9300
C12C—H9C0.9300C26C—C27C1.375 (3)
C13A—C14A1.407 (3)C26C—H18C0.9300
C13B—C14B1.414 (3)C27A—H19A0.9300
C13C—C14C1.412 (3)C27B—H19B0.9300
C14A—C15A1.474 (3)C27C—H19C0.9300
C14B—C15B1.472 (3)N2A—H20A0.92 (2)
C14C—C15C1.476 (3)N2B—H20B0.88 (2)
C15A—N1A1.277 (2)N2C—H20C0.90 (2)
C15A—H10A0.9300
C14A—C1A—C2A123.43 (18)C14A—C15A—H10A118.5
C14A—C1A—C6A119.28 (18)N1B—C15B—C14B121.41 (17)
C2A—C1A—C6A117.23 (19)N1B—C15B—H10B119.3
C14B—C1B—C2B123.36 (18)C14B—C15B—H10B119.3
C14B—C1B—C6B119.08 (19)N1C—C15C—C14C121.23 (18)
C2B—C1B—C6B117.41 (19)N1C—C15C—H10C119.4
C14C—C1C—C2C123.70 (19)C14C—C15C—H10C119.4
C14C—C1C—C6C119.3 (2)C21A—C16A—C17A118.38 (17)
C2C—C1C—C6C117.0 (2)C21A—C16A—N1A118.30 (17)
C3A—C2A—C1A121.3 (2)C17A—C16A—N1A123.33 (17)
C3A—C2A—H1A119.3C21B—C16B—C17B118.03 (17)
C1A—C2A—H1A119.3C21B—C16B—N1B117.53 (16)
C3B—C2B—C1B121.3 (2)C17B—C16B—N1B124.43 (17)
C3B—C2B—H1B119.3C17C—C16C—C21C118.39 (17)
C1B—C2B—H1B119.3C17C—C16C—N1C118.04 (16)
C3C—C2C—C1C121.4 (2)C21C—C16C—N1C123.58 (17)
C3C—C2C—H1C119.3C18A—C17A—C16A120.59 (18)
C1C—C2C—H1C119.3C18A—C17A—H11A119.7
C2A—C3A—C4A121.2 (2)C16A—C17A—H11A119.7
C2A—C3A—H2A119.4C18B—C17B—C16B120.63 (17)
C4A—C3A—H2A119.4C18B—C17B—H11B119.7
C2B—C3B—C4B120.9 (2)C16B—C17B—H11B119.7
C2B—C3B—H2B119.6C16C—C17C—C18C121.43 (18)
C4B—C3B—H2B119.6C16C—C17C—H11C119.3
C2C—C3C—C4C121.4 (2)C18C—C17C—H11C119.3
C2C—C3C—H2C119.3C17A—C18A—C19A121.15 (18)
C4C—C3C—H2C119.3C17A—C18A—H12A119.4
C5A—C4A—C3A119.5 (2)C19A—C18A—H12A119.4
C5A—C4A—H3A120.2C17B—C18B—C19B121.42 (17)
C3A—C4A—H3A120.2C17B—C18B—H12B119.3
C5B—C4B—C3B119.8 (2)C19B—C18B—H12B119.3
C5B—C4B—H3B120.1C17C—C18C—C19C120.67 (18)
C3B—C4B—H3B120.1C17C—C18C—H12C119.7
C5C—C4C—C3C119.5 (2)C19C—C18C—H12C119.7
C5C—C4C—H3C120.3N2A—C19A—C18A117.58 (17)
C3C—C4C—H3C120.3N2A—C19A—C20A124.68 (18)
C4A—C5A—C6A121.6 (2)C18A—C19A—C20A117.64 (17)
C4A—C5A—H4A119.2N2B—C19B—C20B124.79 (17)
C6A—C5A—H4A119.2N2B—C19B—C18B117.73 (17)
C4B—C5B—C6B121.6 (2)C20B—C19B—C18B117.38 (17)
C4B—C5B—H4B119.2N2C—C19C—C18C125.75 (18)
C6B—C5B—H4B119.2N2C—C19C—C20C116.84 (17)
C4C—C5C—C6C121.4 (2)C18C—C19C—C20C117.39 (17)
C4C—C5C—H4C119.3C21A—C20A—C19A120.66 (18)
C6C—C5C—H4C119.3C21A—C20A—H13A119.7
C7A—C6A—C5A121.79 (19)C19A—C20A—H13A119.7
C7A—C6A—C1A119.2 (2)C21B—C20B—C19B120.69 (18)
C5A—C6A—C1A119.0 (2)C21B—C20B—H13B119.7
C7B—C6B—C5B121.58 (19)C19B—C20B—H13B119.7
C7B—C6B—C1B119.42 (19)C21C—C20C—C19C121.62 (17)
C5B—C6B—C1B119.0 (2)C21C—C20C—H14C119.2
C7C—C6C—C5C122.0 (2)C19C—C20C—H14C119.2
C7C—C6C—C1C118.7 (2)C16A—C21A—C20A121.21 (18)
C5C—C6C—C1C119.2 (2)C16A—C21A—H14A119.4
C6A—C7A—C8A122.54 (19)C20A—C21A—H14A119.4
C6A—C7A—H5A118.7C20B—C21B—C16B121.40 (18)
C8A—C7A—H5A118.7C20B—C21B—H14B119.3
C6B—C7B—C8B122.51 (19)C16B—C21B—H14B119.3
C6B—C7B—H5B118.7C20C—C21C—C16C120.38 (18)
C8B—C7B—H5B118.7C20C—C21C—H13C119.8
C8C—C7C—C6C122.8 (2)C16C—C21C—H13C119.8
C8C—C7C—H5C118.6C27A—C22A—C23A117.34 (18)
C6C—C7C—H5C118.6C27A—C22A—N2A125.77 (18)
C7A—C8A—C9A121.5 (2)C23A—C22A—N2A116.86 (18)
C7A—C8A—C13A119.27 (19)C27B—C22B—C23B117.57 (19)
C9A—C8A—C13A119.2 (2)C27B—C22B—N2B125.31 (18)
C7B—C8B—C9B121.69 (19)C23B—C22B—N2B117.07 (18)
C7B—C8B—C13B119.10 (19)C23C—C22C—N2C126.42 (18)
C9B—C8B—C13B119.2 (2)C23C—C22C—C27C117.34 (18)
C7C—C8C—C9C122.3 (2)N2C—C22C—C27C116.23 (17)
C7C—C8C—C13C119.4 (2)C24A—C23A—C22A121.8 (2)
C9C—C8C—C13C118.3 (2)C24A—C23A—H15A119.1
C10A—C9A—C8A121.4 (2)C22A—C23A—H15A119.1
C10A—C9A—H6A119.3C24B—C23B—C22B121.2 (2)
C8A—C9A—H6A119.3C24B—C23B—H15B119.4
C10B—C9B—C8B121.5 (2)C22B—C23B—H15B119.4
C10B—C9B—H6B119.3C24C—C23C—C22C120.61 (19)
C8B—C9B—H6B119.3C24C—C23C—H15C119.7
C10C—C9C—C8C122.3 (2)C22C—C23C—H15C119.7
C10C—C9C—H6C118.9C25A—C24A—C23A120.6 (2)
C8C—C9C—H6C118.9C25A—C24A—H16A119.7
C9A—C10A—C11A120.1 (2)C23A—C24A—H16A119.7
C9A—C10A—H7A120.0C25B—C24B—C23B120.9 (2)
C11A—C10A—H7A120.0C25B—C24B—H16B119.6
C9B—C10B—C11B119.7 (2)C23B—C24B—H16B119.6
C9B—C10B—H7B120.1C25C—C24C—C23C121.4 (2)
C11B—C10B—H7B120.1C25C—C24C—H16C119.3
C9C—C10C—C11C119.4 (2)C23C—C24C—H16C119.3
C9C—C10C—H7C120.3C26A—C25A—C24A118.2 (2)
C11C—C10C—H7C120.3C26A—C25A—H17A120.9
C12A—C11A—C10A121.0 (2)C24A—C25A—H17A120.9
C12A—C11A—H8A119.5C24B—C25B—C26B118.7 (2)
C10A—C11A—H8A119.5C24B—C25B—H17B120.7
C12B—C11B—C10B121.4 (2)C26B—C25B—H17B120.7
C12B—C11B—H8B119.3C24C—C25C—C26C118.6 (2)
C10B—C11B—H8B119.3C24C—C25C—H17C120.7
C12C—C11C—C10C120.8 (3)C26C—C25C—H17C120.7
C12C—C11C—H8C119.6C25A—C26A—C27A121.8 (2)
C10C—C11C—H8C119.6C25A—C26A—H18A119.1
C11A—C12A—C13A120.9 (2)C27A—C26A—H18A119.1
C11A—C12A—H9A119.5C25B—C26B—C27B121.2 (2)
C13A—C12A—H9A119.5C25B—C26B—H18B119.4
C11B—C12B—C13B121.0 (2)C27B—C26B—H18B119.4
C11B—C12B—H9B119.5C27C—C26C—C25C120.5 (2)
C13B—C12B—H9B119.5C27C—C26C—H18C119.7
C11C—C12C—C13C121.4 (2)C25C—C26C—H18C119.7
C11C—C12C—H9C119.3C22A—C27A—C26A120.2 (2)
C13C—C12C—H9C119.3C22A—C27A—H19A119.9
C14A—C13A—C12A123.68 (19)C26A—C27A—H19A119.9
C14A—C13A—C8A118.98 (19)C26B—C27B—C22B120.4 (2)
C12A—C13A—C8A117.34 (19)C26B—C27B—H19B119.8
C14B—C13B—C12B123.45 (18)C22B—C27B—H19B119.8
C14B—C13B—C8B119.23 (19)C26C—C27C—C22C121.4 (2)
C12B—C13B—C8B117.29 (18)C26C—C27C—H19C119.3
C14C—C13C—C12C123.42 (19)C22C—C27C—H19C119.3
C14C—C13C—C8C118.7 (2)C15A—N1A—C16A117.97 (16)
C12C—C13C—C8C117.7 (2)C15B—N1B—C16B119.33 (16)
C13A—C14A—C1A120.68 (18)C15C—N1C—C16C119.17 (16)
C13A—C14A—C15A121.49 (18)C19A—N2A—C22A130.68 (17)
C1A—C14A—C15A117.74 (17)C19A—N2A—H20A114.2 (14)
C13B—C14B—C1B120.57 (18)C22A—N2A—H20A114.1 (13)
C13B—C14B—C15B121.34 (18)C19B—N2B—C22B130.67 (17)
C1B—C14B—C15B117.97 (18)C19B—N2B—H20B114.1 (14)
C1C—C14C—C13C121.10 (19)C22B—N2B—H20B114.5 (14)
C1C—C14C—C15C120.96 (19)C19C—N2C—C22C132.68 (17)
C13C—C14C—C15C117.76 (19)C19C—N2C—H20C112.0 (12)
N1A—C15A—C14A122.92 (18)C22C—N2C—H20C115.3 (12)
N1A—C15A—H10A118.5
C14A—C1A—C2A—C3A179.77 (19)C2B—C1B—C14B—C15B2.5 (3)
C6A—C1A—C2A—C3A−3.1 (3)C6B—C1B—C14B—C15B−172.84 (17)
C14B—C1B—C2B—C3B−176.94 (19)C2C—C1C—C14C—C13C−177.79 (18)
C6B—C1B—C2B—C3B−1.5 (3)C6C—C1C—C14C—C13C0.9 (3)
C14C—C1C—C2C—C3C179.74 (19)C2C—C1C—C14C—C15C7.2 (3)
C6C—C1C—C2C—C3C1.0 (3)C6C—C1C—C14C—C15C−174.09 (18)
C1A—C2A—C3A—C4A0.8 (3)C12C—C13C—C14C—C1C−176.86 (19)
C1B—C2B—C3B—C4B1.0 (3)C8C—C13C—C14C—C1C−0.5 (3)
C1C—C2C—C3C—C4C−0.8 (3)C12C—C13C—C14C—C15C−1.7 (3)
C2A—C3A—C4A—C5A1.6 (3)C8C—C13C—C14C—C15C174.68 (17)
C2B—C3B—C4B—C5B0.0 (3)C13A—C14A—C15A—N1A−41.9 (3)
C2C—C3C—C4C—C5C0.1 (3)C1A—C14A—C15A—N1A134.6 (2)
C3A—C4A—C5A—C6A−1.4 (3)C13B—C14B—C15B—N1B−44.8 (3)
C3B—C4B—C5B—C6B−0.4 (3)C1B—C14B—C15B—N1B131.35 (19)
C3C—C4C—C5C—C6C0.4 (3)C1C—C14C—C15C—N1C48.9 (3)
C4A—C5A—C6A—C7A177.4 (2)C13C—C14C—C15C—N1C−126.3 (2)
C4A—C5A—C6A—C1A−0.9 (3)C21A—C16A—C17A—C18A−4.9 (3)
C14A—C1A—C6A—C7A2.0 (3)N1A—C16A—C17A—C18A175.18 (17)
C2A—C1A—C6A—C7A−175.28 (18)C21B—C16B—C17B—C18B−5.6 (3)
C14A—C1A—C6A—C5A−179.59 (17)N1B—C16B—C17B—C18B173.92 (17)
C2A—C1A—C6A—C5A3.1 (3)C21C—C16C—C17C—C18C−4.0 (3)
C4B—C5B—C6B—C7B178.4 (2)N1C—C16C—C17C—C18C175.62 (17)
C4B—C5B—C6B—C1B−0.1 (3)C16A—C17A—C18A—C19A−0.3 (3)
C14B—C1B—C6B—C7B−1.9 (3)C16B—C17B—C18B—C19B0.4 (3)
C2B—C1B—C6B—C7B−177.54 (18)C16C—C17C—C18C—C19C3.3 (3)
C14B—C1B—C6B—C5B176.68 (18)C17A—C18A—C19A—N2A−178.59 (17)
C2B—C1B—C6B—C5B1.0 (3)C17A—C18A—C19A—C20A4.9 (3)
C4C—C5C—C6C—C7C−179.1 (2)C17B—C18B—C19B—N2B−178.26 (17)
C4C—C5C—C6C—C1C−0.2 (3)C17B—C18B—C19B—C20B5.1 (3)
C14C—C1C—C6C—C7C−0.4 (3)C17C—C18C—C19C—N2C−178.85 (18)
C2C—C1C—C6C—C7C178.43 (18)C17C—C18C—C19C—C20C−0.4 (3)
C14C—C1C—C6C—C5C−179.29 (18)N2A—C19A—C20A—C21A179.34 (18)
C2C—C1C—C6C—C5C−0.5 (3)C18A—C19A—C20A—C21A−4.4 (3)
C5A—C6A—C7A—C8A179.69 (19)N2B—C19B—C20B—C21B178.23 (19)
C1A—C6A—C7A—C8A−2.0 (3)C18B—C19B—C20B—C21B−5.4 (3)
C5B—C6B—C7B—C8B−178.80 (19)N2C—C19C—C20C—C21C176.77 (17)
C1B—C6B—C7B—C8B−0.3 (3)C18C—C19C—C20C—C21C−1.9 (3)
C5C—C6C—C7C—C8C178.2 (2)C17A—C16A—C21A—C20A5.3 (3)
C1C—C6C—C7C—C8C−0.6 (3)N1A—C16A—C21A—C20A−174.70 (18)
C6A—C7A—C8A—C9A−179.57 (19)C19A—C20A—C21A—C16A−0.7 (3)
C6A—C7A—C8A—C13A−0.1 (3)C19B—C20B—C21B—C16B0.3 (3)
C6B—C7B—C8B—C9B−177.34 (19)C17B—C16B—C21B—C20B5.3 (3)
C6B—C7B—C8B—C13B0.9 (3)N1B—C16B—C21B—C20B−174.25 (18)
C6C—C7C—C8C—C9C178.9 (2)C19C—C20C—C21C—C16C1.2 (3)
C6C—C7C—C8C—C13C1.1 (3)C17C—C16C—C21C—C20C1.7 (3)
C7A—C8A—C9A—C10A177.7 (2)N1C—C16C—C21C—C20C−177.85 (17)
C13A—C8A—C9A—C10A−1.7 (3)C27A—C22A—C23A—C24A0.2 (3)
C7B—C8B—C9B—C10B177.1 (2)N2A—C22A—C23A—C24A178.4 (2)
C13B—C8B—C9B—C10B−1.2 (3)C27B—C22B—C23B—C24B1.2 (3)
C7C—C8C—C9C—C10C−177.4 (2)N2B—C22B—C23B—C24B178.7 (2)
C13C—C8C—C9C—C10C0.5 (3)N2C—C22C—C23C—C24C−178.25 (19)
C8A—C9A—C10A—C11A−0.3 (3)C27C—C22C—C23C—C24C0.3 (3)
C8B—C9B—C10B—C11B0.3 (3)C22A—C23A—C24A—C25A1.1 (4)
C8C—C9C—C10C—C11C0.9 (4)C22B—C23B—C24B—C25B0.3 (4)
C9A—C10A—C11A—C12A1.4 (3)C22C—C23C—C24C—C25C1.5 (3)
C9B—C10B—C11B—C12B0.8 (3)C23A—C24A—C25A—C26A−1.1 (3)
C9C—C10C—C11C—C12C−0.9 (4)C23B—C24B—C25B—C26B−1.1 (4)
C10A—C11A—C12A—C13A−0.4 (3)C23C—C24C—C25C—C26C−1.8 (3)
C10B—C11B—C12B—C13B−1.0 (3)C24A—C25A—C26A—C27A−0.3 (3)
C10C—C11C—C12C—C13C−0.6 (3)C24B—C25B—C26B—C27B0.6 (3)
C11A—C12A—C13A—C14A179.49 (19)C24C—C25C—C26C—C27C0.3 (3)
C11A—C12A—C13A—C8A−1.5 (3)C23A—C22A—C27A—C26A−1.6 (3)
C7A—C8A—C13A—C14A2.2 (3)N2A—C22A—C27A—C26A−179.6 (2)
C9A—C8A—C13A—C14A−178.39 (18)C25A—C26A—C27A—C22A1.7 (3)
C7A—C8A—C13A—C12A−176.89 (18)C25B—C26B—C27B—C22B0.9 (3)
C9A—C8A—C13A—C12A2.6 (3)C23B—C22B—C27B—C26B−1.7 (3)
C11B—C12B—C13B—C14B−177.72 (19)N2B—C22B—C27B—C26B−179.06 (19)
C11B—C12B—C13B—C8B0.1 (3)C25C—C26C—C27C—C22C1.4 (3)
C7B—C8B—C13B—C14B0.6 (3)C23C—C22C—C27C—C26C−1.7 (3)
C9B—C8B—C13B—C14B178.89 (17)N2C—C22C—C27C—C26C176.96 (19)
C7B—C8B—C13B—C12B−177.36 (17)C14A—C15A—N1A—C16A−178.47 (17)
C9B—C8B—C13B—C12B1.0 (3)C21A—C16A—N1A—C15A141.24 (19)
C11C—C12C—C13C—C14C178.3 (2)C17A—C16A—N1A—C15A−38.8 (3)
C11C—C12C—C13C—C8C2.0 (3)C14B—C15B—N1B—C16B−176.35 (17)
C7C—C8C—C13C—C14C−0.5 (3)C21B—C16B—N1B—C15B147.60 (18)
C9C—C8C—C13C—C14C−178.42 (19)C17B—C16B—N1B—C15B−31.9 (3)
C7C—C8C—C13C—C12C176.07 (19)C14C—C15C—N1C—C16C178.31 (17)
C9C—C8C—C13C—C12C−1.9 (3)C17C—C16C—N1C—C15C−137.29 (19)
C12A—C13A—C14A—C1A176.92 (18)C21C—C16C—N1C—C15C42.3 (3)
C8A—C13A—C14A—C1A−2.1 (3)C18A—C19A—N2A—C22A165.76 (19)
C12A—C13A—C14A—C15A−6.8 (3)C20A—C19A—N2A—C22A−18.0 (3)
C8A—C13A—C14A—C15A174.26 (17)C27A—C22A—N2A—C19A−12.1 (3)
C2A—C1A—C14A—C13A177.12 (18)C23A—C22A—N2A—C19A169.9 (2)
C6A—C1A—C14A—C13A0.0 (3)C20B—C19B—N2B—C22B−16.8 (3)
C2A—C1A—C14A—C15A0.7 (3)C18B—C19B—N2B—C22B166.81 (19)
C6A—C1A—C14A—C15A−176.46 (17)C27B—C22B—N2B—C19B−11.2 (3)
C12B—C13B—C14B—C1B175.06 (18)C23B—C22B—N2B—C19B171.4 (2)
C8B—C13B—C14B—C1B−2.7 (3)C18C—C19C—N2C—C22C−6.2 (3)
C12B—C13B—C14B—C15B−8.9 (3)C20C—C19C—N2C—C22C175.27 (18)
C8B—C13B—C14B—C15B173.37 (17)C23C—C22C—N2C—C19C−12.3 (3)
C2B—C1B—C14B—C13B178.77 (18)C27C—C22C—N2C—C19C169.19 (19)
C6B—C1B—C14B—C13B3.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg4, Cg10,Cg11, Cg12, Cg13,Cg18, Cg20 and Cg21are the centroids of the C1A–C14A, C16A–C21A, C1B–C14B, C8B–C13B, C16B–C21B, C22B–C27B, C1C–C14C, C22C–C27C and C1C–C8Crings, respectively.
D—H···AD—HH···AD···AD—H···A
C12A—H9A···N1A0.932.442.989 (3)118
C12B—H9B···N1B0.932.473.006 (3)117
C2C—H1C···N1C0.932.513.032 (3)116
N2A—H20A···N1Ai0.92 (2)2.28 (2)3.147 (2)158.4 (18)
N2B—H20B···N1Cii0.88 (2)2.19 (2)3.056 (2)166.2 (19)
N2C—H20C···N1B0.90 (2)2.22 (2)3.094 (2)163.2 (17)
C2A—H1A···Cg13iii0.932.933.7248 (3)144
C2B—H1B···Cg21iv0.932.913.6227 (3)134
C4A—H3A···Cg21v0.932.753.6728 (3)175
C10A—H7A···Cg12ii0.932.803.5075 (3)134
C17A—H11A···Cg18ii0.932.653.5119 (3)154
C17B—H11B···Cg10v0.932.793.6243 (3)150
C17B—H11B···Cg11v0.932.893.7248 (3)150
C21C—H13C···Cg2vi0.932.863.7513 (3)162
C23A—H15A···Cg2i0.932.853.7253 (3)157
C23B—H15B···Cg18ii0.932.873.7057 (3)149
C25A—H17A···Cg20vii0.932.963.6262 (3)130
C25B—H17B···Cg4viii0.933.003.6476 (3)128
C25C—H17C···Cg12iv0.932.843.6263 (3)143
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y, z+1; (iii) x−1, y, z−1; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vi) x, y, z−1; (vii) x−1, −y+3/2, z+1/2; (viii) x+1, y, z.
 

Acknowledgements

The authors are grateful to the National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine, for financial support and Dr Igor Fritsky for helpful discussions.

References

First citationAkiba, K., Yamashita, M., Yamamoto, Y. & Nagase, S. (1999). J. Am. Chem. Soc. 121, 10644–10645.  Web of Science CSD CrossRef CAS Google Scholar
 First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBernhardt, P. V., Moore, E. G. & Riley, M. J. (2001). Inorg. Chem. 40, 5799–5805.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationBrandenberg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, Q. Y. & Chen, C. F. (2004). Tetrahedron Lett. 45, 6493–6496.  Web of Science CrossRef CAS Google Scholar
 First citationFaizi, M. S. H., Gupta, S., Mohan, V. K., Jain, K. V. & Sen, P. (2016). Sens. Actuators B Chem. 222, 15–20.  Web of Science CrossRef CAS Google Scholar
 First citationFaizi, M. S. H., Mashrai, A., Garandal, S. & Shahid, M. (2014). Acta Cryst. E70, o905–o906.  CSD CrossRef IUCr Journals Google Scholar
 First citationFaizi, M. S. H. & Prisyazhnaya, E. V. (2015). Acta Cryst. E71, 261–263.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFritsky, I. O., Świątek-Kozłowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746–3752.  Web of Science CSD CrossRef CAS Google Scholar
 First citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGunnlaugsson, T., Lee, T. C. & Parkesh, R. (2003). Org. Lett. 5, 4065–4068.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKim, S. K. & Yoon, J. (2002). Chem. Commun. pp. 770–771.  Web of Science CrossRef Google Scholar
 First citationPenkova, L., Demeshko, S., Pavlenko, V. A., Dechert, S., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 3036–3040.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationUdhayakumari, D. & Velmathi, S. (2015). Ind. Eng. Chem. Res. 54, 3541–3547.  Web of Science CrossRef CAS Google Scholar
 First citationYamashita, M., Yamamoto, Y., Akiba, K., Hashizume, D., Iwasaki, F., Takagi, N. & Nagase, S. (2005). J. Am. Chem. Soc. 127, 4354–4371.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationYuan, W.-B., Yan, L. & Yang, R.-D. (2004). Acta Cryst. E60, o2447–o2448.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 73| Part 2| February 2017| Pages 137-140
https://doi.org/10.1107/S2056989016020612
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