(E)-N-(1H-Pyrrol-2-yl­methyl­idene)-2-{[(E)-(1H-pyrrol-2-yl­methyl­idene)amino]­meth­yl}aniline

Raghuvarman, B.; Gayathri, J.; Selvan, K.S.; Sugumar, P.; Ponnuswamy, M.N.

doi:10.1107/S2414314617005405

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170540

https://doi.org/10.1107/S2414314617005405

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(E)-N-(1H-Pyrrol-2-ylmethylidene)-2-{[(E)-(1H-pyrrol-2-ylmethylidene)amino]methyl}aniline

B. Raghuvarman,^a Jayagopi Gayathri,^b Kumar Sangeetha Selvan,^b P. Sugumar ^c and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Inorganic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 17 March 2017; accepted 10 April 2017; online 28 April 2017)

The title salophene-type compound, C₁₇H₁₆N₄, crystallizes with two independent molecules (A and B) in the asymmetric unit. Both (pyrrol-2-yl)methanimine groups have an extended conformation, and an E conformation about the C=N bonds. The pyrrole rings are inclined to the aminobenzylamine ring by 43.7 (3) and 78.9 (2)° in molecule A, and by 46.8 (3) and 79.3 (3)° in molecule B, while the pyrrole rings are inclined to one another by 58.9 (3) and 59.9 (3)° in molecules A and B, respectively. In the crystal, molecules are linked by N—H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by C—H⋯π interactions, forming a three-dimensional supramolecular structure.

Keywords: crystal structure; pyrrole; methanimine; salophene; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1543311

Structure description

The title compound was synthesized using Schiff base reactions, which play an important role in coordination chemistry (Ben Guzzi & El Alagi, 2013 ). Schiff bases have been found to exhibit biological activities such as antimicrobial, antibacterial, antifungal, anti-inflammatory, anti-convulsant, antitumor and anti HIV activities (Liu et al. 2007 ; Arulmurugan et al. 2010 ). Salophene [N,N′-bis(salicylidene)-1,2-phenylenediamine] ligands are symmetrical and derived from aromatic 1,2–diamino benzene derivatives. They have received great attention due to their synthetic flexibility, rich coordination chemistry and applications in catalysis. Against this background we have synthesized an asymmetric salophene-type compound and report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. There are two crystallographically independent molecules (A and B) in the asymmetric unit. The pyrrole rings (N1/C2–C5 and N21/C17–C20) are inclined to the aminobenzylamine ring (C8–C13) by 43.7 (3) and 78.9 (2)° in molecule A, and by 46.8 (3) and 79.3 (3)° in molecule B, while the pyrrole rings are inclined to one another by 58.9 (3) and 59.9 (3)° in molecules A and B, respectively. The sum of the bond angles at atoms N1 and N21 of the pyrrole rings are 360.0 and 359.9° in molecule A, and 360.1 and 360.0° in molecule B, typical for sp²-hybridized states.

Figure 1
The molecular structure of one of the two independent molecules of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 30% probability level.

In the crystal, molecules are linked by N—H⋯N hydrogen bonds, forming chains propagating along the a-axis direction (Table 1 and Fig. 2). The chains are linked by C—H⋯π interactions, forming a three-dimensional supramolecular structure (Table 1 and Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg5 are the centroids of rings N1A/C2A–C5A, N21A/C17A–C20A and N21B/C17B–C20B, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯N15Bⁱ	0.86	2.17	2.990 (5)	160
N1B—H1B⋯N15A	0.86	2.20	3.028 (5)	162
N21A—H21A⋯N7B	0.86	2.23	2.984 (5)	146
N21B—H21B⋯N7Aⁱⁱ	0.86	2.15	2.909 (5)	148
C3A—H3A⋯Cg5ⁱⁱⁱ	0.93	2.69	3.465 (6)	142
C10A—H10A⋯Cg2^iv	0.93	2.82	3.654 (6)	151
C20A—H20A⋯Cg1^v	0.93	2.97	3.643 (5)	131
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) x, y-1, z-1; (v) x+1, y, z+1.

Figure 2
The partial view of the crystal packing of title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1

Figure 3
The crystal packing of title compound viewed along the a axis. H atoms not involved in hydrogen bonding (dashed lines) and C—H⋯π interactions (blue arrows) have been omitted for clarity.

Synthesis and crystallization

To a stirred solution of 2-pyrrolecarboxaldehyde 0.950 g (10 mmol) in 20 ml of ethanol, in a round-bottom flask, was added 0.610 g (5 mmol) of 2-amino-benzylamine. The mixture was refluxed for 3 h to give a yellow solution. The final reaction mixture was filtered and the filtrate kept in a refrigerator for 12 h. The resulting yellow block-like crystals were filtered off, washed with cold ethanol and dried under vacuum.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₄
M_r	276.34
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.968 (4), 15.529 (6), 10.119 (4)
β (°)	102.558 (9)
V (Å³)	1528.9 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.982, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	18751, 5057, 3322
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.583

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.092, 0.99
No. of reflections	5057
No. of parameters	380
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1543311

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617005405/su4142sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005405/su4142Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005405/su4142Isup3.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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) top

Crystal data top

C₁₇H₁₆N₄	F(000) = 584
M_r = 276.34	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.968 (4) Å	Cell parameters from 3322 reflections
b = 15.529 (6) Å	θ = 2.4–24.5°
c = 10.119 (4) Å	µ = 0.07 mm⁻¹
β = 102.558 (9)°	T = 296 K
V = 1528.9 (11) Å³	Block, yellow
Z = 4	0.25 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	5057 independent reflections
Radiation source: fine-focus sealed tube	3322 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω and φ scans	θ_max = 24.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.982, T_max = 0.985	k = −18→18
18751 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0351P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
5057 reflections	Δρ_max = 0.15 e Å⁻³
380 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (13)

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

	x	y	z	U_iso*/U_eq
C2A	0.0016 (5)	0.8295 (3)	0.5903 (5)	0.0715 (15)
H2A	−0.0764	0.8156	0.6224	0.086*
C3A	0.0174 (6)	0.9004 (3)	0.5175 (6)	0.0770 (16)
H3A	−0.0471	0.9437	0.4910	0.092*
C4A	0.1469 (5)	0.8965 (3)	0.4897 (5)	0.0717 (14)
H4A	0.1852	0.9369	0.4409	0.086*
C5A	0.2088 (5)	0.8228 (3)	0.5469 (4)	0.0525 (11)
C6A	0.3409 (4)	0.7887 (3)	0.5445 (4)	0.0529 (11)
H6A	0.3999	0.8216	0.5053	0.064*
C8A	0.5163 (4)	0.6869 (2)	0.5839 (4)	0.0439 (10)
C9A	0.5588 (4)	0.6895 (3)	0.4629 (5)	0.0575 (12)
H9A	0.5002	0.7107	0.3854	0.069*
C10A	0.6891 (5)	0.6603 (3)	0.4569 (5)	0.0650 (13)
H10A	0.7183	0.6632	0.3758	0.078*
C11A	0.7745 (5)	0.6275 (3)	0.5696 (6)	0.0635 (13)
H11A	0.8618	0.6081	0.5656	0.076*
C12A	0.7303 (4)	0.6232 (3)	0.6895 (5)	0.0553 (12)
H12A	0.7884	0.6002	0.7658	0.066*
C13A	0.6013 (4)	0.6524 (2)	0.6991 (4)	0.0432 (10)
C14A	0.5551 (4)	0.6468 (3)	0.8314 (4)	0.0541 (12)
H14A	0.4763	0.6841	0.8278	0.065*
H14B	0.5272	0.5883	0.8452	0.065*
C16A	0.7137 (4)	0.6145 (3)	1.0305 (4)	0.0464 (10)
H16A	0.6722	0.5605	1.0208	0.056*
C17A	0.8277 (4)	0.6277 (3)	1.1407 (4)	0.0441 (10)
C18A	0.8902 (4)	0.5727 (3)	1.2417 (4)	0.0572 (12)
H18A	0.8627	0.5166	1.2538	0.069*
C19A	1.0010 (5)	0.6147 (3)	1.3225 (5)	0.0664 (13)
H19A	1.0614	0.5922	1.3977	0.080*
C20A	1.0042 (4)	0.6951 (3)	1.2705 (5)	0.0647 (13)
H20A	1.0679	0.7377	1.3045	0.078*
N1A	0.1186 (3)	0.7820 (2)	0.6087 (4)	0.0561 (10)
H1A	0.1332	0.7342	0.6523	0.067*
N7A	0.3822 (3)	0.7153 (2)	0.5935 (3)	0.0464 (9)
N15A	0.6657 (3)	0.6724 (2)	0.9444 (4)	0.0477 (9)
N21A	0.8989 (3)	0.7029 (2)	1.1607 (3)	0.0522 (9)
H21A	0.8801	0.7483	1.1116	0.063*
C2B	0.5320 (5)	0.8966 (3)	0.8313 (5)	0.0734 (15)
H2B	0.4489	0.8697	0.8322	0.088*
C3B	0.5475 (6)	0.9768 (4)	0.7837 (5)	0.0830 (16)
H3B	0.4772	1.0146	0.7461	0.100*
C4B	0.6876 (6)	0.9924 (3)	0.8013 (5)	0.0773 (15)
H4B	0.7279	1.0425	0.7779	0.093*
C5B	0.7559 (5)	0.9202 (3)	0.8597 (4)	0.0556 (12)
C6B	0.9002 (5)	0.9050 (3)	0.9028 (5)	0.0567 (12)
H6B	0.9605	0.9462	0.8829	0.068*
C8B	1.0951 (4)	0.8292 (3)	1.0099 (4)	0.0504 (11)
C9B	1.1750 (5)	0.8937 (3)	1.0846 (5)	0.0701 (14)
H9B	1.1342	0.9450	1.1024	0.084*
C10B	1.3143 (5)	0.8815 (4)	1.1321 (5)	0.0786 (15)
H10B	1.3671	0.9244	1.1828	0.094*
C11B	1.3744 (5)	0.8068 (4)	1.1049 (5)	0.0731 (15)
H11B	1.4685	0.7990	1.1356	0.088*
C12B	1.2953 (4)	0.7420 (3)	1.0313 (4)	0.0626 (13)
H12B	1.3372	0.6910	1.0138	0.075*
C13B	1.1560 (4)	0.7521 (3)	0.9838 (4)	0.0496 (11)
C14B	1.0713 (4)	0.6807 (3)	0.9077 (5)	0.0609 (13)
H14C	1.0533	0.6379	0.9715	0.073*
H14D	0.9837	0.7036	0.8597	0.073*
C16B	1.1674 (4)	0.5599 (3)	0.8283 (4)	0.0509 (11)
H16B	1.1401	0.5323	0.8997	0.061*
C17B	1.2371 (4)	0.5098 (3)	0.7451 (4)	0.0438 (10)
C18B	1.2663 (5)	0.4240 (3)	0.7486 (5)	0.0645 (13)
H18B	1.2441	0.3841	0.8089	0.077*
C19B	1.3351 (5)	0.4067 (3)	0.6462 (6)	0.0709 (15)
H19B	1.3678	0.3533	0.6260	0.085*
C20B	1.3460 (4)	0.4812 (3)	0.5813 (5)	0.0625 (13)
H20B	1.3878	0.4883	0.5083	0.075*
N1B	0.6582 (4)	0.8626 (2)	0.8772 (4)	0.0571 (10)
H1B	0.6745	0.8121	0.9122	0.068*
N7B	0.9502 (3)	0.8376 (2)	0.9672 (4)	0.0515 (9)
N15B	1.1404 (3)	0.6396 (2)	0.8111 (3)	0.0501 (9)
N21B	1.2854 (3)	0.5437 (2)	0.6407 (3)	0.0467 (8)
H21B	1.2786	0.5969	0.6163	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2A	0.057 (3)	0.067 (4)	0.085 (4)	0.014 (3)	0.002 (3)	−0.021 (3)
C3A	0.083 (4)	0.046 (3)	0.086 (4)	0.024 (3)	−0.015 (3)	−0.007 (3)
C4A	0.083 (4)	0.044 (3)	0.078 (4)	0.007 (3)	−0.005 (3)	0.007 (3)
C5A	0.064 (3)	0.038 (3)	0.051 (3)	0.007 (2)	0.001 (2)	0.003 (2)
C6A	0.061 (3)	0.045 (3)	0.051 (3)	−0.007 (2)	0.009 (2)	0.006 (2)
C8A	0.047 (2)	0.036 (2)	0.049 (3)	−0.005 (2)	0.012 (2)	0.002 (2)
C9A	0.070 (3)	0.055 (3)	0.050 (3)	−0.004 (2)	0.018 (2)	0.003 (2)
C10A	0.078 (3)	0.058 (3)	0.071 (4)	−0.002 (3)	0.043 (3)	−0.005 (3)
C11A	0.062 (3)	0.054 (3)	0.082 (4)	0.001 (2)	0.033 (3)	−0.003 (3)
C12A	0.048 (3)	0.055 (3)	0.062 (3)	0.000 (2)	0.009 (2)	−0.001 (2)
C13A	0.045 (2)	0.039 (2)	0.047 (3)	−0.0040 (19)	0.012 (2)	−0.001 (2)
C14A	0.046 (2)	0.067 (3)	0.047 (3)	−0.003 (2)	0.006 (2)	0.004 (2)
C16A	0.052 (2)	0.047 (3)	0.043 (3)	0.000 (2)	0.018 (2)	−0.001 (2)
C17A	0.049 (2)	0.047 (3)	0.037 (3)	0.008 (2)	0.011 (2)	−0.002 (2)
C18A	0.065 (3)	0.060 (3)	0.047 (3)	0.010 (2)	0.014 (2)	0.011 (3)
C19A	0.064 (3)	0.083 (4)	0.049 (3)	0.016 (3)	0.004 (2)	0.008 (3)
C20A	0.059 (3)	0.083 (4)	0.049 (3)	0.000 (3)	0.005 (3)	−0.009 (3)
N1A	0.059 (2)	0.049 (2)	0.057 (3)	0.011 (2)	0.0046 (19)	0.0025 (19)
N7A	0.050 (2)	0.045 (2)	0.042 (2)	0.0020 (16)	0.0056 (16)	0.0066 (17)
N15A	0.0473 (19)	0.050 (2)	0.044 (2)	0.0010 (17)	0.0059 (17)	0.0038 (19)
N21A	0.058 (2)	0.055 (2)	0.041 (2)	0.0046 (19)	0.0060 (18)	0.0022 (19)
C2B	0.066 (3)	0.083 (4)	0.069 (4)	0.017 (3)	0.011 (3)	0.008 (3)
C3B	0.091 (4)	0.081 (4)	0.075 (4)	0.030 (3)	0.012 (3)	0.017 (3)
C4B	0.103 (4)	0.058 (4)	0.071 (4)	0.008 (3)	0.020 (3)	0.009 (3)
C5B	0.072 (3)	0.049 (3)	0.046 (3)	0.003 (3)	0.015 (2)	0.003 (2)
C6B	0.072 (3)	0.052 (3)	0.049 (3)	−0.008 (3)	0.020 (2)	−0.004 (2)
C8B	0.052 (3)	0.052 (3)	0.048 (3)	−0.010 (2)	0.013 (2)	0.002 (2)
C9B	0.075 (3)	0.055 (3)	0.076 (4)	−0.017 (3)	0.009 (3)	−0.007 (3)
C10B	0.078 (4)	0.083 (4)	0.067 (4)	−0.026 (3)	−0.001 (3)	−0.001 (3)
C11B	0.058 (3)	0.096 (4)	0.064 (4)	−0.016 (3)	0.008 (3)	0.003 (3)
C12B	0.057 (3)	0.074 (4)	0.060 (3)	−0.004 (3)	0.018 (2)	−0.004 (3)
C13B	0.048 (3)	0.056 (3)	0.048 (3)	−0.008 (2)	0.017 (2)	−0.004 (2)
C14B	0.056 (3)	0.064 (3)	0.068 (3)	−0.007 (2)	0.025 (2)	−0.015 (3)
C16B	0.056 (3)	0.051 (3)	0.047 (3)	−0.012 (2)	0.014 (2)	0.000 (2)
C17B	0.045 (2)	0.044 (3)	0.041 (3)	−0.004 (2)	0.005 (2)	0.003 (2)
C18B	0.073 (3)	0.044 (3)	0.073 (4)	0.000 (2)	0.010 (3)	0.011 (3)
C19B	0.074 (3)	0.042 (3)	0.093 (4)	0.016 (2)	0.009 (3)	−0.011 (3)
C20B	0.058 (3)	0.060 (3)	0.071 (3)	0.009 (3)	0.016 (2)	−0.013 (3)
N1B	0.070 (2)	0.048 (2)	0.053 (3)	0.006 (2)	0.012 (2)	0.0033 (19)
N7B	0.059 (2)	0.044 (2)	0.051 (2)	−0.0041 (18)	0.0122 (18)	−0.0031 (19)
N15B	0.055 (2)	0.048 (2)	0.051 (2)	−0.0017 (18)	0.0180 (17)	−0.0071 (19)
N21B	0.0483 (19)	0.040 (2)	0.050 (2)	0.0032 (17)	0.0059 (17)	0.0003 (18)

Geometric parameters (Å, º) top

C2A—C3A	1.353 (6)	C2B—N1B	1.351 (5)
C2A—N1A	1.358 (5)	C2B—C3B	1.357 (7)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.380 (7)	C3B—C4B	1.389 (7)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.368 (5)	C4B—C5B	1.376 (6)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—N1A	1.358 (5)	C5B—N1B	1.362 (5)
C5A—C6A	1.424 (6)	C5B—C6B	1.429 (6)
C6A—N7A	1.276 (5)	C6B—N7B	1.276 (5)
C6A—H6A	0.9300	C6B—H6B	0.9300
C8A—C9A	1.380 (5)	C8B—C13B	1.393 (5)
C8A—C13A	1.390 (5)	C8B—C9B	1.395 (5)
C8A—N7A	1.431 (4)	C8B—N7B	1.421 (5)
C9A—C10A	1.389 (6)	C9B—C10B	1.380 (6)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.365 (6)	C10B—C11B	1.362 (7)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.380 (6)	C11B—C12B	1.390 (6)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.387 (5)	C12B—C13B	1.377 (5)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.509 (5)	C13B—C14B	1.501 (5)
C14A—N15A	1.461 (5)	C14B—N15B	1.459 (5)
C14A—H14A	0.9700	C14B—H14C	0.9700
C14A—H14B	0.9700	C14B—H14D	0.9700
C16A—N15A	1.272 (4)	C16B—N15B	1.270 (5)
C16A—C17A	1.423 (5)	C16B—C17B	1.433 (6)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—N21A	1.359 (5)	C17B—N21B	1.359 (5)
C17A—C18A	1.372 (5)	C17B—C18B	1.362 (5)
C18A—C19A	1.386 (6)	C18B—C19B	1.387 (6)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.357 (6)	C19B—C20B	1.346 (6)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—N21A	1.358 (5)	C20B—N21B	1.352 (5)
C20A—H20A	0.9300	C20B—H20B	0.9300
N1A—H1A	0.8600	N1B—H1B	0.8600
N21A—H21A	0.8600	N21B—H21B	0.8600

C3A—C2A—N1A	108.5 (4)	N1B—C2B—C3B	108.2 (5)
C3A—C2A—H2A	125.7	N1B—C2B—H2B	125.9
N1A—C2A—H2A	125.7	C3B—C2B—H2B	125.9
C2A—C3A—C4A	107.5 (4)	C2B—C3B—C4B	107.6 (5)
C2A—C3A—H3A	126.2	C2B—C3B—H3B	126.2
C4A—C3A—H3A	126.2	C4B—C3B—H3B	126.2
C5A—C4A—C3A	107.8 (5)	C5B—C4B—C3B	107.7 (5)
C5A—C4A—H4A	126.1	C5B—C4B—H4B	126.2
C3A—C4A—H4A	126.1	C3B—C4B—H4B	126.2
N1A—C5A—C4A	107.5 (4)	N1B—C5B—C4B	106.9 (4)
N1A—C5A—C6A	122.8 (4)	N1B—C5B—C6B	123.5 (4)
C4A—C5A—C6A	129.6 (5)	C4B—C5B—C6B	129.6 (5)
N7A—C6A—C5A	123.2 (4)	N7B—C6B—C5B	123.2 (4)
N7A—C6A—H6A	118.4	N7B—C6B—H6B	118.4
C5A—C6A—H6A	118.4	C5B—C6B—H6B	118.4
C9A—C8A—C13A	120.5 (4)	C13B—C8B—C9B	119.9 (4)
C9A—C8A—N7A	121.5 (4)	C13B—C8B—N7B	118.5 (4)
C13A—C8A—N7A	118.0 (4)	C9B—C8B—N7B	121.4 (4)
C8A—C9A—C10A	119.9 (4)	C10B—C9B—C8B	120.2 (5)
C8A—C9A—H9A	120.0	C10B—C9B—H9B	119.9
C10A—C9A—H9A	120.0	C8B—C9B—H9B	119.9
C11A—C10A—C9A	120.3 (4)	C11B—C10B—C9B	120.0 (5)
C11A—C10A—H10A	119.9	C11B—C10B—H10B	120.0
C9A—C10A—H10A	119.9	C9B—C10B—H10B	120.0
C10A—C11A—C12A	119.5 (4)	C10B—C11B—C12B	120.1 (4)
C10A—C11A—H11A	120.2	C10B—C11B—H11B	119.9
C12A—C11A—H11A	120.2	C12B—C11B—H11B	119.9
C11A—C12A—C13A	121.6 (4)	C13B—C12B—C11B	121.1 (4)
C11A—C12A—H12A	119.2	C13B—C12B—H12B	119.5
C13A—C12A—H12A	119.2	C11B—C12B—H12B	119.5
C12A—C13A—C8A	118.2 (4)	C12B—C13B—C8B	118.7 (4)
C12A—C13A—C14A	120.6 (4)	C12B—C13B—C14B	120.4 (4)
C8A—C13A—C14A	121.2 (3)	C8B—C13B—C14B	120.9 (3)
N15A—C14A—C13A	110.8 (3)	N15B—C14B—C13B	111.8 (3)
N15A—C14A—H14A	109.5	N15B—C14B—H14C	109.3
C13A—C14A—H14A	109.5	C13B—C14B—H14C	109.3
N15A—C14A—H14B	109.5	N15B—C14B—H14D	109.3
C13A—C14A—H14B	109.5	C13B—C14B—H14D	109.3
H14A—C14A—H14B	108.1	H14C—C14B—H14D	107.9
N15A—C16A—C17A	123.5 (4)	N15B—C16B—C17B	124.4 (4)
N15A—C16A—H16A	118.2	N15B—C16B—H16B	117.8
C17A—C16A—H16A	118.2	C17B—C16B—H16B	117.8
N21A—C17A—C18A	106.6 (4)	N21B—C17B—C18B	106.8 (4)
N21A—C17A—C16A	122.8 (4)	N21B—C17B—C16B	123.0 (4)
C18A—C17A—C16A	130.5 (4)	C18B—C17B—C16B	130.2 (5)
C17A—C18A—C19A	108.7 (4)	C17B—C18B—C19B	107.9 (4)
C17A—C18A—H18A	125.6	C17B—C18B—H18B	126.0
C19A—C18A—H18A	125.6	C19B—C18B—H18B	126.0
C20A—C19A—C18A	106.7 (4)	C20B—C19B—C18B	107.7 (4)
C20A—C19A—H19A	126.7	C20B—C19B—H19B	126.2
C18A—C19A—H19A	126.7	C18B—C19B—H19B	126.2
C19A—C20A—N21A	108.7 (4)	C19B—C20B—N21B	108.0 (4)
C19A—C20A—H20A	125.7	C19B—C20B—H20B	126.0
N21A—C20A—H20A	125.7	N21B—C20B—H20B	126.0
C2A—N1A—C5A	108.6 (4)	C2B—N1B—C5B	109.7 (4)
C2A—N1A—H1A	125.7	C2B—N1B—H1B	125.2
C5A—N1A—H1A	125.7	C5B—N1B—H1B	125.2
C6A—N7A—C8A	118.4 (3)	C6B—N7B—C8B	119.3 (4)
C16A—N15A—C14A	116.8 (3)	C16B—N15B—C14B	116.8 (4)
C20A—N21A—C17A	109.3 (4)	C20B—N21B—C17B	109.6 (4)
C20A—N21A—H21A	125.3	C20B—N21B—H21B	125.2
C17A—N21A—H21A	125.3	C17B—N21B—H21B	125.2

N1A—C2A—C3A—C4A	0.2 (6)	N1B—C2B—C3B—C4B	−0.1 (6)
C2A—C3A—C4A—C5A	−0.1 (6)	C2B—C3B—C4B—C5B	0.2 (6)
C3A—C4A—C5A—N1A	0.0 (5)	C3B—C4B—C5B—N1B	−0.2 (5)
C3A—C4A—C5A—C6A	178.5 (4)	C3B—C4B—C5B—C6B	−177.3 (5)
N1A—C5A—C6A—N7A	4.0 (7)	N1B—C5B—C6B—N7B	−3.4 (7)
C4A—C5A—C6A—N7A	−174.4 (4)	C4B—C5B—C6B—N7B	173.3 (5)
C13A—C8A—C9A—C10A	−2.3 (6)	C13B—C8B—C9B—C10B	0.4 (7)
N7A—C8A—C9A—C10A	−179.2 (3)	N7B—C8B—C9B—C10B	175.8 (4)
C8A—C9A—C10A—C11A	1.3 (6)	C8B—C9B—C10B—C11B	0.7 (7)
C9A—C10A—C11A—C12A	0.1 (7)	C9B—C10B—C11B—C12B	−1.1 (8)
C10A—C11A—C12A—C13A	−0.7 (6)	C10B—C11B—C12B—C13B	0.5 (7)
C11A—C12A—C13A—C8A	−0.2 (6)	C11B—C12B—C13B—C8B	0.5 (6)
C11A—C12A—C13A—C14A	179.8 (4)	C11B—C12B—C13B—C14B	−178.3 (4)
C9A—C8A—C13A—C12A	1.7 (6)	C9B—C8B—C13B—C12B	−1.0 (6)
N7A—C8A—C13A—C12A	178.7 (3)	N7B—C8B—C13B—C12B	−176.6 (4)
C9A—C8A—C13A—C14A	−178.3 (4)	C9B—C8B—C13B—C14B	177.9 (4)
N7A—C8A—C13A—C14A	−1.3 (5)	N7B—C8B—C13B—C14B	2.3 (6)
C12A—C13A—C14A—N15A	42.8 (5)	C12B—C13B—C14B—N15B	−42.3 (6)
C8A—C13A—C14A—N15A	−137.2 (4)	C8B—C13B—C14B—N15B	138.9 (4)
N15A—C16A—C17A—N21A	−2.6 (6)	N15B—C16B—C17B—N21B	2.1 (6)
N15A—C16A—C17A—C18A	179.3 (4)	N15B—C16B—C17B—C18B	−176.5 (4)
N21A—C17A—C18A—C19A	−0.7 (5)	N21B—C17B—C18B—C19B	1.0 (5)
C16A—C17A—C18A—C19A	177.6 (4)	C16B—C17B—C18B—C19B	179.8 (4)
C17A—C18A—C19A—C20A	0.5 (5)	C17B—C18B—C19B—C20B	−0.5 (5)
C18A—C19A—C20A—N21A	−0.1 (5)	C18B—C19B—C20B—N21B	−0.2 (5)
C3A—C2A—N1A—C5A	−0.3 (5)	C3B—C2B—N1B—C5B	0.0 (6)
C4A—C5A—N1A—C2A	0.2 (5)	C4B—C5B—N1B—C2B	0.2 (5)
C6A—C5A—N1A—C2A	−178.5 (4)	C6B—C5B—N1B—C2B	177.5 (4)
C5A—C6A—N7A—C8A	179.1 (4)	C5B—C6B—N7B—C8B	−178.0 (4)
C9A—C8A—N7A—C6A	−49.7 (5)	C13B—C8B—N7B—C6B	−132.0 (4)
C13A—C8A—N7A—C6A	133.3 (4)	C9B—C8B—N7B—C6B	52.5 (6)
C17A—C16A—N15A—C14A	175.5 (3)	C17B—C16B—N15B—C14B	−178.7 (3)
C13A—C14A—N15A—C16A	−114.5 (4)	C13B—C14B—N15B—C16B	119.1 (4)
C19A—C20A—N21A—C17A	−0.3 (5)	C19B—C20B—N21B—C17B	0.8 (5)
C18A—C17A—N21A—C20A	0.6 (4)	C18B—C17B—N21B—C20B	−1.1 (4)
C16A—C17A—N21A—C20A	−177.8 (3)	C16B—C17B—N21B—C20B	−180.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg5 are the centroids of rings N1A/C2A–C5A, N21A/C17A–C20A and N21B/C17B–C20B, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N15Bⁱ	0.86	2.17	2.990 (5)	160
N1B—H1B···N15A	0.86	2.20	3.028 (5)	162
N21A—H21A···N7B	0.86	2.23	2.984 (5)	146
N21B—H21B···N7Aⁱⁱ	0.86	2.15	2.909 (5)	148
C3A—H3A···Cg5ⁱⁱⁱ	0.93	2.69	3.465 (6)	142
C10A—H10A···Cg2^iv	0.93	2.82	3.654 (6)	151
C20A—H20A···Cg1^v	0.93	2.97	3.643 (5)	131

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

Acknowledgements

The authors thank TBI consultancy, University of Madras, India, for the data collection

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