4,4′-Methyl­enebis[N-(2-hy­droxy-3-meth­oxy­benzyl­idene)-2,6-diiso­propyl­aniline]

Prapakaran, T.; Murugavel, R.

doi:10.1107/S2414314622007933

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 8| August 2022| x220793

https://doi.org/10.1107/S2414314622007933

Open

access

4,4′-Methylenebis[N-(2-hydroxy-3-methoxybenzylidene)-2,6-diisopropylaniline]

Tulasi Prapakaran ^a and Ramaswamy Murugavel ^a ^*

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India
^*Correspondence e-mail: rmv@chem.iitb.ac.in

Edited by R. J. Butcher, Howard University, USA (Received 20 May 2022; accepted 5 August 2022; online 26 August 2022)

In the V-shaped title Schiff base, C₄₁H₅₀N₂O₄, the planes of the benzene rings of the central diphenylmethane unit make a dihedral angle of 70.40 (5)°, whereas the planes of the neighbouring benzene and ortho-vanilin rings are twisted with respect to one another by dihedral angles of 75.76 (5) and 73.89 (6)°. The Schiff base displays intramolecular O—H⋯N hydrogen bonds and weak intermolecular C—H⋯O contacts.

Keywords: crystal structure; bis-bidentate bulky Schiff base; hydrogen bonding.

CCDC reference: 2195233

Structure description

Bis-bidentate Schiff ligands have been widely used as building blocks in metallo-supramolecular chemistry (Xu et al., 2015 ; Chu & Huang, 2007 ; Birkedal & Pattison, 2006 ). Additionally, these compounds have been employed as thermosetting resins (Lin et al., 2008 ). We are interested in such ligands because of their diverse applications in coordination chemistry and their single molecular magnetic and luminescent properties (Cucos et al., 2014 ; Habib et al., 2012 ; Taneda et al., 2004 , 2009 ; Novitchi et al., 2008 ). As part of our ongoing studies in this area, we describe here the synthesis and characterization of the title ortho-vanillin-based bis-bidentate Schiff base. The reaction of 4,4′–methylene-bis(2,6–diisopropylanilne) with o-vanillin led to the formation of 4,4′-methylenebis[N-(2-hydroxy-3-methoxybenzylidene)-2,6-diisopropylaniline] (Fig. 1).

Figure 1
Reaction scheme.

The asymmetric unit of the title molecule contains one molecule (Fig. 2). The dihedral angle between the planes of the benzene rings bonded to the central methylene group is 70.4 (5)°. The phenyl and o-vanillin rings are nearly perpendicular to one another, with dihedral angles of 75.76 (5)° and 73.89 (6)°. The N1—C26 and N2—C34 bond lengths [1.281 (2) and 1.278 (2) Å] support the double-bond nature of the C—N bonds. The molecule exhibits an imine E configuration with C1—N1—C26—C27 and C11—N2—C34—C35 torsion angles of 179.37 (16) and 177.85 (15)°, respectively. In the molecule, atoms N1 and N2 of the imine moieties serve as hydrogen-bond acceptors, with adjacent phenol groups forming an intramolecular O—H⋯N hydrogen bond. The closest intermolecular contact is C41—H41B⋯O2 (at x, y, 1 + z), resulting in zigzag chain formation (Table 1). Fig. 3 depicts the packing of the title compound.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.87 (2)	1.79 (2)	2.5912 (17)	153 (2)
O1—H1⋯N1	0.87 (2)	1.80 (2)	2.5991 (19)	153 (2)
C41—H41B⋯O2ⁱ	0.98	2.49	3.452 (3)	168
Symmetry code: (i) x, y, z+1.

Figure 2
The molecular crystal structure of compound 1. Ellipsoids represent the 50% probability level. C-bonded H atoms are omitted.

Figure 3
Crystal packing of compound 1 viewed down the a axis.

Synthesis and crystallization

4,4′–Methylene-bis(2,6–diisopropylanilne) (1 g, 2.72 mmol) and o-vanilin (0.870 g, 5.72 mmol) were dissolved in methanol (40 ml) and heated under reflux overnight, resulting in a yellow solution that was filtered and crystallized by slow evaporation at room temperature. The crystals were filtered and washed with cold methanol and dried under reduced pressure (985 mg, 56% yield, m.p. 143°C). Analysis calculated for (%) C₄₁H₅₀N₂O₄: C, 77.57; H, 7.94; N, 4.41. Found: C, 76.99; H, 7.96; N, 4.18. FT–IR (KBr pellet) 3447 cm⁻¹ [m, ν (O—H)], 2959 cm⁻¹ [s, ν (Ar—H)], 1621 cm⁻¹ [s, ν (C=N)]. ¹H NMR (CDCl₃, 500 MHz) δ p.p.m. 1.15 (d, 12H), 3.0 (m, 2H, CHMe₂), 4.0 (s, 3H, OMe), 4.01 (s, 2H, CH₂), 6.89–6.97 (m, 3H), 7.03 (s, 2H), 8.30 (s, 1H, CH=N), 13.62 (br, 1H, OH). ¹³C NMR (CDCl₃, 125 MHz) δ p.p.m. 23.7, 28.3, 41.8, 56.3, 114.7, 118.7, 123.7, 138.2, 144, 148.7, 151.6, 167.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₄₁H₅₀N₂O₄
M_r	634.83
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	6.0155 (1), 16.5935 (3), 19.2093 (3)
α, β, γ (°)	101.541 (2), 97.341 (2), 92.928 (2)
V (Å³)	1857.47 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.45 × 0.14 × 0.10

Data collection
Diffractometer	Rigaku Saturn 724+
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2017 $[Rigaku, OD (2017). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.701, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14358, 6528, 5207
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.03
No. of reflections	6528
No. of parameters	440
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.17
Computer programs: CrysAlis PRO (Rigaku OD, 2017 $[Rigaku, OD (2017). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXT2015 (Sheldrick, 2015a ), SHELXL2015 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2195233

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622007933/bv4044sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314622007933/bv4044Isup2.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

4,4'-Methylenebis[N-(2-hydroxy-3-methoxybenzylidene)-2,6-diisopropylaniline] top

Crystal data top

C₄₁H₅₀N₂O₄	Z = 2
M_r = 634.83	F(000) = 684
Triclinic, P1	D_x = 1.135 Mg m⁻³
a = 6.0155 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.5935 (3) Å	Cell parameters from 9193 reflections
c = 19.2093 (3) Å	θ = 2.3–31.1°
α = 101.541 (2)°	µ = 0.07 mm⁻¹
β = 97.341 (2)°	T = 150 K
γ = 92.928 (2)°	Needle, yellow
V = 1857.47 (6) Å³	0.45 × 0.14 × 0.1 mm

Data collection top

Rigaku Saturn 724+ diffractometer	6528 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2017)	h = −7→7
T_min = 0.701, T_max = 1.000	k = −19→15
14358 measured reflections	l = −21→22

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0537P)² + 0.623P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6528 reflections	Δρ_max = 0.36 e Å⁻³
440 parameters	Δρ_min = −0.17 e Å⁻³
2 restraints

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
O3	1.0025 (2)	0.74747 (8)	0.94420 (6)	0.0440 (3)
H3	0.951 (3)	0.7684 (12)	0.9080 (9)	0.053*
O1	0.7058 (2)	0.60969 (8)	0.22598 (7)	0.0516 (4)
H1	0.681 (4)	0.6413 (12)	0.2656 (9)	0.062*
N2	0.7464 (2)	0.82044 (8)	0.86122 (7)	0.0331 (3)
O4	1.0694 (3)	0.68864 (8)	1.06103 (7)	0.0578 (4)
N1	0.5193 (3)	0.67089 (8)	0.33770 (7)	0.0382 (3)
O2	0.6886 (3)	0.49933 (10)	0.10588 (8)	0.0728 (5)
C11	0.6910 (3)	0.84537 (10)	0.79454 (8)	0.0319 (4)
C1	0.5145 (3)	0.73131 (10)	0.40200 (8)	0.0359 (4)
C40	0.8509 (3)	0.76246 (9)	0.99044 (8)	0.0354 (4)
C12	0.8185 (3)	0.91305 (10)	0.78247 (9)	0.0365 (4)
C10	0.5268 (3)	0.79864 (10)	0.74104 (8)	0.0355 (4)
C34	0.6145 (3)	0.83185 (10)	0.90880 (8)	0.0371 (4)
H34	0.481609	0.858880	0.899791	0.044*
C6	0.6688 (3)	0.72676 (10)	0.46248 (8)	0.0373 (4)
C35	0.6612 (3)	0.80476 (10)	0.97640 (8)	0.0368 (4)
C39	0.8850 (3)	0.73198 (10)	1.05412 (9)	0.0419 (4)
C2	0.3717 (3)	0.79565 (10)	0.40243 (9)	0.0389 (4)
C26	0.3601 (3)	0.61353 (10)	0.31618 (9)	0.0406 (4)
H26	0.240549	0.611575	0.343812	0.049*
C20	0.4027 (3)	0.72003 (11)	0.74959 (9)	0.0415 (4)
H20	0.465958	0.708075	0.796857	0.050*
C27	0.3567 (3)	0.55148 (10)	0.25099 (9)	0.0437 (5)
C17	0.8142 (3)	0.65446 (11)	0.46037 (9)	0.0429 (4)
H17	0.850517	0.638445	0.410326	0.052*
C13	0.7696 (3)	0.93566 (10)	0.71661 (9)	0.0443 (5)
H13	0.854035	0.981442	0.707478	0.053*
C9	0.4843 (3)	0.82531 (11)	0.67685 (9)	0.0440 (4)
H9	0.370611	0.795636	0.640563	0.053*
C32	0.5288 (3)	0.55181 (10)	0.20858 (9)	0.0450 (5)
C5	0.6753 (3)	0.78841 (11)	0.52375 (9)	0.0445 (5)
H5	0.778531	0.786489	0.565046	0.053*
C8	0.6012 (4)	0.89338 (10)	0.66378 (9)	0.0479 (5)
C14	0.2141 (3)	0.80248 (11)	0.33507 (9)	0.0455 (5)
H14	0.156626	0.745187	0.309572	0.055*
C23	1.0007 (3)	0.96050 (11)	0.84052 (10)	0.0430 (4)
H23	1.060884	0.920571	0.869481	0.052*
C4	0.5351 (4)	0.85284 (10)	0.52639 (9)	0.0484 (5)
C38	0.7348 (4)	0.74707 (12)	1.10290 (10)	0.0541 (5)
H38	0.757654	0.726711	1.145902	0.065*
C3	0.3853 (4)	0.85535 (11)	0.46560 (9)	0.0461 (5)
H3A	0.289154	0.899146	0.467117	0.055*
C22	0.4396 (3)	0.64662 (11)	0.69073 (10)	0.0492 (5)
H22A	0.375698	0.656181	0.643808	0.074*
H22B	0.365593	0.596154	0.699171	0.074*
H22C	0.601106	0.640609	0.691609	0.074*
C25	0.9011 (4)	1.02789 (12)	0.89148 (11)	0.0559 (5)
H25A	0.837631	1.067768	0.864671	0.084*
H25B	1.019478	1.056175	0.929668	0.084*
H25C	0.782346	1.002839	0.912677	0.084*
C15	0.3467 (4)	0.83974 (13)	0.28492 (9)	0.0506 (5)
H15A	0.414913	0.894536	0.309715	0.076*
H15B	0.245340	0.844596	0.242036	0.076*
H15C	0.465146	0.804004	0.270828	0.076*
C36	0.5113 (4)	0.81944 (14)	1.02708 (10)	0.0561 (5)
H36	0.382589	0.848622	1.017936	0.067*
C19	1.0370 (3)	0.67380 (14)	0.51052 (11)	0.0572 (5)
H19A	1.115965	0.723219	0.501878	0.086*
H19B	1.130050	0.627070	0.501414	0.086*
H19C	1.008032	0.683539	0.560462	0.086*
C18	0.6850 (4)	0.57976 (12)	0.47611 (12)	0.0582 (5)
H18A	0.649514	0.592890	0.525320	0.087*
H18B	0.777577	0.532586	0.470693	0.087*
H18C	0.545238	0.565974	0.442407	0.087*
C31	0.5186 (4)	0.49171 (12)	0.14498 (10)	0.0564 (6)
C30	0.3394 (5)	0.43240 (13)	0.12604 (12)	0.0692 (7)
H30	0.333160	0.391143	0.083543	0.083*
C16	0.0106 (4)	0.85078 (14)	0.35006 (12)	0.0578 (5)
H16A	−0.068439	0.827835	0.384144	0.087*
H16B	−0.091097	0.846769	0.305168	0.087*
H16C	0.060441	0.908807	0.370516	0.087*
C24	1.1994 (4)	0.99674 (13)	0.81108 (13)	0.0617 (6)
H24A	1.256611	0.953185	0.777110	0.093*
H24B	1.319035	1.019800	0.850773	0.093*
H24C	1.149822	1.040428	0.786503	0.093*
C41	1.1111 (5)	0.65391 (13)	1.12360 (10)	0.0706 (7)
H41A	1.248975	0.624954	1.122168	0.106*
H41B	0.984325	0.614930	1.124753	0.106*
H41C	1.128626	0.698107	1.166670	0.106*
C37	0.5509 (4)	0.79164 (15)	1.08980 (11)	0.0638 (6)
H37	0.451395	0.803020	1.124549	0.077*
C28	0.1750 (4)	0.49100 (12)	0.22983 (12)	0.0594 (6)
H28	0.056929	0.490900	0.258265	0.071*
C29	0.1685 (5)	0.43223 (13)	0.16819 (14)	0.0733 (7)
H29	0.046251	0.391143	0.154217	0.088*
C7	0.5468 (5)	0.92094 (12)	0.59319 (10)	0.0707 (7)
H7A	0.662509	0.964598	0.590916	0.085*
H7B	0.400484	0.945705	0.592621	0.085*
C21	0.1526 (4)	0.73049 (15)	0.75052 (13)	0.0664 (6)
H21A	0.132640	0.773893	0.791564	0.100*
H21B	0.076116	0.678439	0.754658	0.100*
H21C	0.088405	0.745873	0.705952	0.100*
C33	0.6978 (6)	0.43475 (17)	0.04340 (12)	0.0931 (10)
H33A	0.562963	0.433193	0.008493	0.140*
H33B	0.705075	0.381452	0.057866	0.140*
H33C	0.831693	0.445924	0.021586	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0572 (8)	0.0496 (7)	0.0265 (6)	0.0123 (6)	0.0014 (6)	0.0118 (5)
O1	0.0671 (9)	0.0487 (8)	0.0317 (7)	−0.0023 (7)	0.0012 (6)	−0.0034 (6)
N2	0.0405 (8)	0.0335 (7)	0.0220 (7)	0.0002 (6)	−0.0033 (6)	0.0037 (5)
O4	0.0913 (11)	0.0533 (8)	0.0309 (7)	0.0170 (8)	−0.0017 (7)	0.0175 (6)
N1	0.0505 (9)	0.0356 (8)	0.0252 (7)	−0.0078 (7)	−0.0046 (6)	0.0073 (6)
O2	0.1026 (13)	0.0644 (10)	0.0392 (8)	0.0231 (9)	−0.0028 (9)	−0.0140 (7)
C11	0.0403 (10)	0.0314 (8)	0.0231 (8)	0.0068 (7)	0.0005 (7)	0.0048 (6)
C1	0.0474 (10)	0.0339 (9)	0.0238 (8)	−0.0136 (8)	−0.0004 (7)	0.0074 (7)
C40	0.0528 (11)	0.0272 (8)	0.0206 (8)	−0.0070 (7)	−0.0016 (7)	−0.0014 (6)
C12	0.0456 (10)	0.0312 (8)	0.0308 (9)	0.0059 (7)	0.0013 (8)	0.0039 (7)
C10	0.0440 (10)	0.0347 (9)	0.0253 (8)	0.0049 (7)	−0.0012 (7)	0.0035 (7)
C34	0.0405 (10)	0.0394 (9)	0.0271 (8)	0.0012 (8)	−0.0028 (8)	0.0021 (7)
C6	0.0467 (10)	0.0373 (9)	0.0269 (8)	−0.0122 (8)	−0.0015 (7)	0.0123 (7)
C35	0.0463 (10)	0.0367 (9)	0.0227 (8)	−0.0068 (8)	−0.0007 (7)	0.0010 (7)
C39	0.0659 (13)	0.0292 (9)	0.0247 (8)	−0.0065 (8)	−0.0062 (8)	0.0023 (7)
C2	0.0539 (11)	0.0337 (9)	0.0279 (9)	−0.0103 (8)	−0.0018 (8)	0.0118 (7)
C26	0.0509 (11)	0.0346 (9)	0.0340 (9)	−0.0047 (8)	−0.0066 (8)	0.0120 (7)
C20	0.0504 (11)	0.0399 (10)	0.0304 (9)	−0.0043 (8)	−0.0043 (8)	0.0068 (7)
C27	0.0602 (12)	0.0292 (9)	0.0358 (9)	−0.0024 (8)	−0.0153 (9)	0.0084 (7)
C17	0.0464 (11)	0.0505 (11)	0.0301 (9)	−0.0055 (8)	−0.0015 (8)	0.0109 (8)
C13	0.0710 (13)	0.0282 (9)	0.0331 (9)	0.0016 (8)	0.0050 (9)	0.0069 (7)
C9	0.0633 (12)	0.0355 (9)	0.0264 (9)	0.0033 (8)	−0.0115 (8)	0.0015 (7)
C32	0.0642 (13)	0.0312 (9)	0.0330 (9)	0.0043 (9)	−0.0162 (9)	0.0055 (7)
C5	0.0675 (13)	0.0390 (10)	0.0237 (8)	−0.0121 (9)	−0.0084 (8)	0.0124 (7)
C8	0.0873 (15)	0.0297 (9)	0.0239 (9)	0.0063 (9)	−0.0018 (9)	0.0045 (7)
C14	0.0637 (13)	0.0357 (9)	0.0329 (9)	−0.0065 (9)	−0.0103 (9)	0.0108 (7)
C23	0.0467 (11)	0.0372 (9)	0.0414 (10)	−0.0026 (8)	−0.0061 (8)	0.0086 (8)
C4	0.0871 (15)	0.0305 (9)	0.0255 (9)	−0.0078 (9)	−0.0034 (9)	0.0113 (7)
C38	0.0837 (16)	0.0504 (11)	0.0261 (9)	−0.0100 (11)	0.0034 (10)	0.0096 (8)
C3	0.0752 (14)	0.0320 (9)	0.0307 (9)	−0.0014 (9)	−0.0002 (9)	0.0118 (7)
C22	0.0581 (12)	0.0363 (10)	0.0476 (11)	−0.0005 (9)	−0.0047 (9)	0.0046 (8)
C25	0.0630 (14)	0.0471 (11)	0.0463 (11)	−0.0044 (10)	−0.0065 (10)	−0.0063 (9)
C15	0.0654 (13)	0.0596 (12)	0.0289 (9)	0.0106 (10)	0.0017 (9)	0.0161 (8)
C36	0.0599 (13)	0.0714 (14)	0.0363 (10)	0.0052 (11)	0.0093 (10)	0.0082 (10)
C19	0.0514 (12)	0.0735 (14)	0.0452 (11)	−0.0060 (10)	−0.0057 (9)	0.0193 (10)
C18	0.0619 (14)	0.0443 (11)	0.0690 (14)	−0.0009 (10)	−0.0026 (11)	0.0222 (10)
C31	0.0854 (16)	0.0401 (11)	0.0355 (10)	0.0170 (11)	−0.0143 (11)	0.0001 (8)
C30	0.108 (2)	0.0358 (11)	0.0472 (12)	0.0088 (12)	−0.0302 (14)	−0.0061 (9)
C16	0.0529 (13)	0.0660 (13)	0.0571 (13)	−0.0065 (10)	0.0005 (10)	0.0264 (11)
C24	0.0530 (13)	0.0530 (12)	0.0765 (15)	−0.0077 (10)	0.0031 (11)	0.0139 (11)
C41	0.129 (2)	0.0532 (12)	0.0291 (10)	0.0189 (13)	−0.0073 (12)	0.0165 (9)
C37	0.0763 (16)	0.0821 (16)	0.0348 (11)	−0.0007 (13)	0.0162 (11)	0.0128 (10)
C28	0.0726 (15)	0.0379 (10)	0.0572 (13)	−0.0126 (10)	−0.0186 (11)	0.0069 (9)
C29	0.097 (2)	0.0386 (12)	0.0668 (15)	−0.0155 (12)	−0.0330 (15)	0.0029 (11)
C7	0.144 (2)	0.0361 (10)	0.0273 (10)	0.0050 (12)	−0.0084 (12)	0.0081 (8)
C21	0.0582 (14)	0.0677 (14)	0.0706 (15)	−0.0051 (11)	0.0169 (12)	0.0056 (12)
C33	0.141 (3)	0.0810 (18)	0.0415 (13)	0.0436 (18)	−0.0069 (15)	−0.0201 (12)

Geometric parameters (Å, º) top

O3—H3	0.867 (15)	C14—C16	1.524 (3)
O3—C40	1.351 (2)	C23—H23	1.0000
O1—H1	0.867 (15)	C23—C25	1.532 (3)
O1—C32	1.358 (2)	C23—C24	1.532 (3)
N2—C11	1.4283 (19)	C4—C3	1.390 (3)
N2—C34	1.278 (2)	C4—C7	1.522 (2)
O4—C39	1.359 (2)	C38—H38	0.9500
O4—C41	1.433 (2)	C38—C37	1.386 (3)
N1—C1	1.431 (2)	C3—H3A	0.9500
N1—C26	1.281 (2)	C22—H22A	0.9800
O2—C31	1.359 (3)	C22—H22B	0.9800
O2—C33	1.449 (2)	C22—H22C	0.9800
C11—C12	1.402 (2)	C25—H25A	0.9800
C11—C10	1.406 (2)	C25—H25B	0.9800
C1—C6	1.408 (2)	C25—H25C	0.9800
C1—C2	1.404 (3)	C15—H15A	0.9800
C40—C35	1.395 (3)	C15—H15B	0.9800
C40—C39	1.410 (2)	C15—H15C	0.9800
C12—C13	1.391 (2)	C36—H36	0.9500
C12—C23	1.521 (2)	C36—C37	1.372 (3)
C10—C20	1.518 (2)	C19—H19A	0.9800
C10—C9	1.390 (2)	C19—H19B	0.9800
C34—H34	0.9500	C19—H19C	0.9800
C34—C35	1.456 (2)	C18—H18A	0.9800
C6—C17	1.517 (3)	C18—H18B	0.9800
C6—C5	1.391 (2)	C18—H18C	0.9800
C35—C36	1.405 (3)	C31—C30	1.382 (3)
C39—C38	1.379 (3)	C30—H30	0.9500
C2—C14	1.530 (2)	C30—C29	1.388 (4)
C2—C3	1.395 (2)	C16—H16A	0.9800
C26—H26	0.9500	C16—H16B	0.9800
C26—C27	1.450 (2)	C16—H16C	0.9800
C20—H20	1.0000	C24—H24A	0.9800
C20—C22	1.534 (2)	C24—H24B	0.9800
C20—C21	1.525 (3)	C24—H24C	0.9800
C27—C32	1.397 (3)	C41—H41A	0.9800
C27—C28	1.406 (3)	C41—H41B	0.9800
C17—H17	1.0000	C41—H41C	0.9800
C17—C19	1.527 (3)	C37—H37	0.9500
C17—C18	1.531 (3)	C28—H28	0.9500
C13—H13	0.9500	C28—C29	1.370 (3)
C13—C8	1.388 (3)	C29—H29	0.9500
C9—H9	0.9500	C7—H7A	0.9900
C9—C8	1.382 (3)	C7—H7B	0.9900
C32—C31	1.406 (3)	C21—H21A	0.9800
C5—H5	0.9500	C21—H21B	0.9800
C5—C4	1.392 (3)	C21—H21C	0.9800
C8—C7	1.518 (2)	C33—H33A	0.9800
C14—H14	1.0000	C33—H33B	0.9800
C14—C15	1.527 (3)	C33—H33C	0.9800

C40—O3—H3	105.0 (13)	C2—C3—H3A	118.9
C32—O1—H1	104.8 (15)	C4—C3—C2	122.13 (18)
C34—N2—C11	120.48 (14)	C4—C3—H3A	118.9
C39—O4—C41	117.77 (17)	C20—C22—H22A	109.5
C26—N1—C1	120.19 (15)	C20—C22—H22B	109.5
C31—O2—C33	117.5 (2)	C20—C22—H22C	109.5
C12—C11—N2	117.70 (14)	H22A—C22—H22B	109.5
C12—C11—C10	121.75 (14)	H22A—C22—H22C	109.5
C10—C11—N2	120.32 (14)	H22B—C22—H22C	109.5
C6—C1—N1	117.43 (16)	C23—C25—H25A	109.5
C2—C1—N1	120.55 (15)	C23—C25—H25B	109.5
C2—C1—C6	121.87 (15)	C23—C25—H25C	109.5
O3—C40—C35	122.38 (14)	H25A—C25—H25B	109.5
O3—C40—C39	118.06 (16)	H25A—C25—H25C	109.5
C35—C40—C39	119.54 (16)	H25B—C25—H25C	109.5
C11—C12—C23	120.51 (15)	C14—C15—H15A	109.5
C13—C12—C11	117.75 (16)	C14—C15—H15B	109.5
C13—C12—C23	121.73 (16)	C14—C15—H15C	109.5
C11—C10—C20	123.08 (14)	H15A—C15—H15B	109.5
C9—C10—C11	117.40 (16)	H15A—C15—H15C	109.5
C9—C10—C20	119.48 (15)	H15B—C15—H15C	109.5
N2—C34—H34	118.9	C35—C36—H36	120.0
N2—C34—C35	122.13 (16)	C37—C36—C35	120.0 (2)
C35—C34—H34	118.9	C37—C36—H36	120.0
C1—C6—C17	120.00 (15)	C17—C19—H19A	109.5
C5—C6—C1	117.76 (16)	C17—C19—H19B	109.5
C5—C6—C17	122.20 (15)	C17—C19—H19C	109.5
C40—C35—C34	120.49 (15)	H19A—C19—H19B	109.5
C40—C35—C36	119.71 (16)	H19A—C19—H19C	109.5
C36—C35—C34	119.78 (17)	H19B—C19—H19C	109.5
O4—C39—C40	114.75 (16)	C17—C18—H18A	109.5
O4—C39—C38	125.72 (16)	C17—C18—H18B	109.5
C38—C39—C40	119.53 (18)	C17—C18—H18C	109.5
C1—C2—C14	121.32 (15)	H18A—C18—H18B	109.5
C3—C2—C1	117.64 (16)	H18A—C18—H18C	109.5
C3—C2—C14	120.98 (16)	H18B—C18—H18C	109.5
N1—C26—H26	118.9	O2—C31—C32	115.3 (2)
N1—C26—C27	122.13 (18)	O2—C31—C30	125.46 (19)
C27—C26—H26	118.9	C30—C31—C32	119.3 (2)
C10—C20—H20	107.8	C31—C30—H30	119.5
C10—C20—C22	111.11 (15)	C31—C30—C29	121.0 (2)
C10—C20—C21	111.23 (16)	C29—C30—H30	119.5
C22—C20—H20	107.8	C14—C16—H16A	109.5
C21—C20—H20	107.8	C14—C16—H16B	109.5
C21—C20—C22	110.92 (16)	C14—C16—H16C	109.5
C32—C27—C26	121.01 (16)	H16A—C16—H16B	109.5
C32—C27—C28	119.76 (18)	H16A—C16—H16C	109.5
C28—C27—C26	119.21 (19)	H16B—C16—H16C	109.5
C6—C17—H17	107.3	C23—C24—H24A	109.5
C6—C17—C19	114.19 (16)	C23—C24—H24B	109.5
C6—C17—C18	110.88 (15)	C23—C24—H24C	109.5
C19—C17—H17	107.3	H24A—C24—H24B	109.5
C19—C17—C18	109.68 (16)	H24A—C24—H24C	109.5
C18—C17—H17	107.3	H24B—C24—H24C	109.5
C12—C13—H13	119.0	O4—C41—H41A	109.5
C8—C13—C12	122.04 (17)	O4—C41—H41B	109.5
C8—C13—H13	119.0	O4—C41—H41C	109.5
C10—C9—H9	118.8	H41A—C41—H41B	109.5
C8—C9—C10	122.50 (17)	H41A—C41—H41C	109.5
C8—C9—H9	118.8	H41B—C41—H41C	109.5
O1—C32—C27	122.06 (16)	C38—C37—H37	119.7
O1—C32—C31	118.3 (2)	C36—C37—C38	120.5 (2)
C27—C32—C31	119.67 (19)	C36—C37—H37	119.7
C6—C5—H5	119.0	C27—C28—H28	120.0
C6—C5—C4	122.02 (16)	C29—C28—C27	120.0 (2)
C4—C5—H5	119.0	C29—C28—H28	120.0
C13—C8—C7	120.93 (18)	C30—C29—H29	119.8
C9—C8—C13	118.42 (16)	C28—C29—C30	120.4 (2)
C9—C8—C7	120.65 (18)	C28—C29—H29	119.8
C2—C14—H14	107.4	C8—C7—C4	114.93 (15)
C15—C14—C2	109.56 (16)	C8—C7—H7A	108.5
C15—C14—H14	107.4	C8—C7—H7B	108.5
C16—C14—C2	114.26 (16)	C4—C7—H7A	108.5
C16—C14—H14	107.4	C4—C7—H7B	108.5
C16—C14—C15	110.48 (15)	H7A—C7—H7B	107.5
C12—C23—H23	107.2	C20—C21—H21A	109.5
C12—C23—C25	110.64 (15)	C20—C21—H21B	109.5
C12—C23—C24	113.66 (16)	C20—C21—H21C	109.5
C25—C23—H23	107.2	H21A—C21—H21B	109.5
C24—C23—H23	107.2	H21A—C21—H21C	109.5
C24—C23—C25	110.75 (16)	H21B—C21—H21C	109.5
C5—C4—C7	121.60 (17)	O2—C33—H33A	109.5
C3—C4—C5	118.58 (16)	O2—C33—H33B	109.5
C3—C4—C7	119.80 (18)	O2—C33—H33C	109.5
C39—C38—H38	119.7	H33A—C33—H33B	109.5
C39—C38—C37	120.64 (18)	H33A—C33—H33C	109.5
C37—C38—H38	119.7	H33B—C33—H33C	109.5

O3—C40—C35—C34	2.5 (2)	C6—C1—C2—C14	176.57 (15)
O3—C40—C35—C36	−179.12 (16)	C6—C1—C2—C3	−0.7 (2)
O3—C40—C39—O4	−1.1 (2)	C6—C5—C4—C3	−0.3 (3)
O3—C40—C39—C38	179.22 (16)	C6—C5—C4—C7	−178.75 (18)
O1—C32—C31—O2	−1.5 (2)	C35—C40—C39—O4	177.23 (15)
O1—C32—C31—C30	−179.72 (17)	C35—C40—C39—C38	−2.4 (2)
N2—C11—C12—C13	177.89 (15)	C35—C36—C37—C38	−1.8 (3)
N2—C11—C12—C23	−3.2 (2)	C39—C40—C35—C34	−175.79 (15)
N2—C11—C10—C20	−0.9 (2)	C39—C40—C35—C36	2.6 (3)
N2—C11—C10—C9	−178.65 (15)	C39—C38—C37—C36	1.9 (3)
N2—C34—C35—C40	−2.1 (3)	C2—C1—C6—C17	177.89 (15)
N2—C34—C35—C36	179.51 (17)	C2—C1—C6—C5	0.3 (2)
O4—C39—C38—C37	−179.43 (19)	C26—N1—C1—C6	108.15 (19)
N1—C1—C6—C17	−6.6 (2)	C26—N1—C1—C2	−76.2 (2)
N1—C1—C6—C5	175.87 (15)	C26—C27—C32—O1	−0.1 (3)
N1—C1—C2—C14	1.2 (2)	C26—C27—C32—C31	−178.83 (16)
N1—C1—C2—C3	−176.08 (15)	C26—C27—C28—C29	179.62 (18)
N1—C26—C27—C32	0.0 (3)	C20—C10—C9—C8	−175.86 (17)
N1—C26—C27—C28	−178.98 (17)	C27—C32—C31—O2	177.26 (16)
O2—C31—C30—C29	−177.0 (2)	C27—C32—C31—C30	−1.0 (3)
C11—N2—C34—C35	177.84 (15)	C27—C28—C29—C30	−0.6 (3)
C11—C12—C13—C8	−0.1 (3)	C17—C6—C5—C4	−177.33 (17)
C11—C12—C23—C25	−86.5 (2)	C13—C12—C23—C25	92.4 (2)
C11—C12—C23—C24	148.19 (17)	C13—C12—C23—C24	−33.0 (2)
C11—C10—C20—C22	−121.14 (18)	C13—C8—C7—C4	130.3 (2)
C11—C10—C20—C21	114.75 (19)	C9—C10—C20—C22	56.6 (2)
C11—C10—C9—C8	2.0 (3)	C9—C10—C20—C21	−67.5 (2)
C1—N1—C26—C27	179.37 (15)	C9—C8—C7—C4	−49.5 (3)
C1—C6—C17—C19	153.14 (16)	C32—C27—C28—C29	0.6 (3)
C1—C6—C17—C18	−82.3 (2)	C32—C31—C30—C29	1.1 (3)
C1—C6—C5—C4	0.2 (3)	C5—C6—C17—C19	−29.4 (2)
C1—C2—C14—C15	−79.1 (2)	C5—C6—C17—C18	95.1 (2)
C1—C2—C14—C16	156.29 (16)	C5—C4—C3—C2	−0.1 (3)
C1—C2—C3—C4	0.5 (3)	C5—C4—C7—C8	−34.7 (3)
C40—C35—C36—C37	−0.5 (3)	C14—C2—C3—C4	−176.71 (17)
C40—C39—C38—C37	0.2 (3)	C23—C12—C13—C8	−179.00 (17)
C12—C11—C10—C20	173.55 (15)	C3—C2—C14—C15	98.0 (2)
C12—C11—C10—C9	−4.2 (2)	C3—C2—C14—C16	−26.6 (2)
C12—C13—C8—C9	−2.0 (3)	C3—C4—C7—C8	146.9 (2)
C12—C13—C8—C7	178.19 (19)	C31—C30—C29—C28	−0.3 (3)
C10—C11—C12—C13	3.3 (2)	C41—O4—C39—C40	−178.36 (16)
C10—C11—C12—C23	−177.79 (15)	C41—O4—C39—C38	1.3 (3)
C10—C9—C8—C13	1.0 (3)	C28—C27—C32—O1	178.83 (16)
C10—C9—C8—C7	−179.16 (19)	C28—C27—C32—C31	0.1 (3)
C34—N2—C11—C12	109.56 (18)	C7—C4—C3—C2	178.41 (19)
C34—N2—C11—C10	−75.8 (2)	C33—O2—C31—C32	174.40 (18)
C34—C35—C36—C37	177.86 (19)	C33—O2—C31—C30	−7.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.87 (2)	1.79 (2)	2.5912 (17)	153 (2)
O1—H1···N1	0.87 (2)	1.80 (2)	2.5991 (19)	153 (2)
C41—H41B···O2ⁱ	0.98	2.49	3.452 (3)	168

Symmetry code: (i) x, y, z+1.

Acknowledgements

TP acknowledges IIT Bombay and SERB SUPRA for a research fellowship. The authors thank the central facilities at IIT Bombay for various characterization data.

Funding information

Funding for this research was provided by: Science and Engineering Research Board (award No. SB/S2/JCB-85/2014 & 2020).

References

Birkedal, H. & Pattison, P. (2006). Acta Cryst. C62, o139–o141. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Chu, Z. & Huang, W. (2007). J. Mol. Struct. 837, 15–22. Web of Science CSD CrossRef CAS Google Scholar
Cucos, P., Tuna, F., Sorace, L., Matei, I., Maxim, C., Shova, S., Gheorghe, R., Caneschi, A., Hillebrand, M. & Andruh, M. (2014). Inorg. Chem. 53, 7738–7747. CSD CrossRef CAS PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Habib, F., Long, J., Lin, P.-H., Korobkov, I., Ungur, L., Wernsdorfer, W., Chibotaru, L. F. & Murugesu, M. (2012). Chem. Sci. 3, 2158–2164. CSD CrossRef CAS Google Scholar
Lin, C. H., Chang, S. L., Hsieh, C. W. & Lee, H. H. (2008). Polymer, 49, 1220–1229. Web of Science CrossRef CAS Google Scholar
Novitchi, G., Costes, J.-P., Tuchagues, J.-P., Vendier, L. & Wernsdorfer, W. (2008). New J. Chem. 32, 197–200. CSD CrossRef CAS Google Scholar
Rigaku, OD (2017). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Taneda, M., Amimoto, K., Koyama, H. & Kawato, T. (2004). Org. Biomol. Chem. 2, 499–504. Web of Science CSD CrossRef PubMed CAS Google Scholar
Taneda, M., Koyama, H. & Kawato, T. (2009). Res. Chem. Intermed. 35, 643–650. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, L., Zhu, L.-C., Ma, J.-C., Zhang, Y., Zhang, J. & Dong, W.-K. (2015). Z. Anorg. Allg. Chem. 641, 2520–2524. CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.