2-Amino-4-(4-meth­oxy­phen­yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbo­nitrile acetic acid monosolvate

Chakraborty, B.B.; Paul, S.; Anwar, S.; Choudhury, S.

doi:10.1107/S2414314623005588

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 6| June 2023| x230558

https://doi.org/10.1107/S2414314623005588

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2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate

Bimal Bhushan Chakraborty,^a Saurav Paul,^a Siddique Anwar ^a and Sudip Choudhury ^b ^*

^aDepartment of Chemistry, Assam University, Silchar 788011, India, and ^bCentre for Soft Matter, Department of Chemistry, Assam University, Silchar 788011, India
^*Correspondence e-mail: sudip.choudhury@aus.ac.in

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 17 March 2023; accepted 23 June 2023; online 30 June 2023)

In the title co-crystal, C₂₀H₁₄N₂O₄·C₂H₄O₂, the expected proton transfer from acetic acid to amine has not occurred. In the crystal, the chromene molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds to generate [100] columns. The acetic acid molecules form inversion dimers linked by pairwise O—H⋯O hydrogen bonds and occupy voids between the columns.

Keywords: crystal structure; co-crystal; acetic acid dimer; chromene; carbonitrile.

CCDC reference: 2271965

Structure description

Pyrano[3,2-c]chromene derivatives enjoy attention from researchers due to their pharmacological activity (Siziani et al., 2022 ; Tashrifi et al., 2020 ), heavy metal chemisensing (Mohajer et al., 2022 ), semiconductivity (Mal et al., 2022 ), etc. As part of our studies in this area, the crystal structure of the 1:1 co-crystal of 2-amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile and acetic acid is now reported. The compound was crystallized from acetic acid, but the expected proton transfer from the carboxylic acid to the amine group did not occur.

The title compound crystallizes in the triclinic space group P $[\overline{1}]$ with one pyrano[3,2-c]chromene molecule and one acetic acid molecule in the asymmetric unit (Fig. 1). Unexpectedly, although crystallized from a solvent of glacial acetic acid, the –NH₂ group present in the pyranochromene framework was not protonated. The dihedral angle between the planes of the C1–C12/O2/O3 fused ring (r.m.s. deviation = 0.079 Å) and the pendant C14–C19 ring is 89.00 (6)°, and the C atom of the methoxy substituent deviates by 0.132 (2) Å from its attached ring.

Figure 1
Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

In the crystal, the pyrano[3,2-c]chromene molecules are linked by N1—H11⋯N2ⁱ hydrogen bonds (Table 1) to generate centrosymmetric R₂²(12) loops and the dimers are linked into [100] chains by N1—H10⋯O1ⁱⁱ links to generate [100] columns. The acetic acid molecules maintain their hydrogen-bonded dimeric form (via pairwise O6—H15⋯O5ⁱⁱⁱ links) without any directional interactions with the pyrano[3,2-c]chromene columns (Fig. 2). The acetic acid dimers occupy the space between pyranochromene columns (about 7.4 Å) and are positioned approximately parallel to the pyranochromene plane of the host molecule; a weak C15—H6⋯O5 hydrogen bond occurs between host and guest. The significant difference between the lengths of the C21—O5 [1.197 (3) Å] and C21—O6 [1.284 (3) Å] bonds infers that the acetic acid molecule remains in its protonated state.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N2ⁱ	0.85 (2)	2.22 (2)	3.062 (2)	172 (2)
N1—H10⋯O1ⁱⁱ	0.81 (2)	2.31 (2)	3.111 (2)	168 (2)
O6—H15⋯O5ⁱⁱⁱ	1.00 (4)	1.67 (4)	2.664 (3)	172 (3)
C15—H6⋯O5	0.93	2.39	3.251 (2)	154
Symmetry codes: (i) ; (ii) x+1, y, z; (iii) .

Figure 2
Packing arrangement of the title compound. Hydrogen bonds are shown as dotted lines.

Synthesis and crystallization

4-Hydroxycoumarin or 4-hydroxy-2H-benzo[h]chromen-2-one (1.00 mmol), 4-methoxybenzaldehyde (1.00 mmol), malononitrile (1.00 mmol) and catalyst DABCO (10 mol%) were ground with a mortar and pestle for about 10 min. Upon completion of the reaction, the product was washed several times with ethanol to get the pure product, a white solid. The purity of the compound was confirmed by fluorescent HPTLC (Merck) and melting point (observed 238°C, reported 237°C; Shaabani et al., 2007 ). FT–IR (KBr, cm⁻¹): 3360, 3184, 2980, 1726, 1596, 1462; ¹H NMR (400 MHz, DMSO-d₆): 3.73 (s, 3H), 4.40 (s, 1H), 6.89 (d, 2H, J = 8.8 Hz, 7.19 (d, 2H, J = 8.4 Hz), 7.35 (s, 2H), 7.52–7.40 (m, 2H), 7.73 (dt, 1H, J = 8.8, 1.6 Hz), 7.92 (dd, J = 8.0, 1.6 Hz); ¹³C NMR (100 MHz, DMSO-d₆): 36.1, 55.0, 58.3, 104.3, 112.9, 113.9, 116.5, 119.2, 122.4, 124.6, 128.7, 132.8, 135.4, 152.1, 153.1, 157.9, 158.3, 159.5. Suitable crystals of the title compound were grown by dissolving the compound in glacial acetic acid. The solution was kept undisturbed for a period of two weeks in an NMR tube (OD 5 mm) and the grown crystals were carefully recovered and washed with hexane and dried.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₄N₂O₄·C₂H₄O₂
M_r	406.38
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	7.9303 (6), 11.2977 (9), 11.9988 (9)
α, β, γ (°)	82.468 (4), 77.379 (4), 73.419 (4)
V (Å³)	1002.71 (14)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.36 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	17101, 4807, 3457
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.157, 1.06
No. of reflections	4807
No. of parameters	285
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25
Computer programs: APEX2 and SAINT (Bruker 2015 ), SHELXT2018 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ; Bourhis et al., 2015 ).

Structural data

CCDC reference: 2271965

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623005588/hb4427sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314623005588/hb4427Isup3.mol

checkCIF report

Computing details top

Data collection: SAINT (Bruker 2015); cell refinement: APEX2 (Bruker 2015); data reduction: SAINT (Bruker 2015); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015).

2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate top

Crystal data top

C₂₀H₁₄N₂O₄·C₂H₄O₂	F(000) = 424
M_r = 406.38	D_x = 1.346 Mg m⁻³
Triclinic, P1	Melting point: 511.15 K
a = 7.9303 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2977 (9) Å	Cell parameters from 5371 reflections
c = 11.9988 (9) Å	θ = 2.7–27.9°
α = 82.468 (4)°	µ = 0.10 mm⁻¹
β = 77.379 (4)°	T = 296 K
γ = 73.419 (4)°	Block, white
V = 1002.71 (14) Å³	0.36 × 0.36 × 0.30 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3457 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 28.1°, θ_min = 2.7°
φ and ω scans	h = −10→10
17101 measured reflections	k = −14→14
4807 independent reflections	l = −15→15

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.050	w = 1/[σ²(F_o²) + (0.0858P)² + 0.1068P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.157	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.30 e Å⁻³
4807 reflections	Δρ_min = −0.24 e Å⁻³
285 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.037 (6)
Primary atom site location: iterative

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
C1	0.28503 (19)	0.15224 (13)	0.94770 (12)	0.0398 (3)
C2	0.46268 (18)	0.13992 (12)	0.87929 (11)	0.0343 (3)
C3	0.59600 (18)	0.14624 (12)	0.92882 (11)	0.0351 (3)
C4	0.5684 (2)	0.16975 (12)	1.04776 (11)	0.0388 (3)
C5	0.3950 (2)	0.18548 (13)	1.10966 (11)	0.0416 (3)
C6	0.7039 (2)	0.17741 (15)	1.10147 (13)	0.0506 (4)
H4	0.820649	0.167223	1.060769	0.061*
C7	0.6624 (3)	0.20027 (18)	1.21552 (15)	0.0649 (5)
H3	0.752115	0.204468	1.252281	0.078*
C8	0.4892 (3)	0.21697 (18)	1.27573 (14)	0.0662 (5)
H2	0.463455	0.233314	1.352487	0.079*
C9	0.3539 (3)	0.20992 (16)	1.22439 (13)	0.0566 (4)
H1	0.237323	0.221273	1.265566	0.068*
C10	0.81505 (19)	0.09187 (13)	0.76421 (11)	0.0372 (3)
C11	0.69033 (18)	0.08117 (12)	0.70792 (11)	0.0350 (3)
C12	0.49036 (17)	0.12492 (12)	0.75303 (10)	0.0339 (3)
H5	0.434598	0.060982	0.742969	0.041*
C13	0.74784 (19)	0.03627 (13)	0.59735 (12)	0.0414 (3)
C14	0.40507 (17)	0.24512 (12)	0.68869 (10)	0.0345 (3)
C15	0.4317 (2)	0.35587 (13)	0.70738 (13)	0.0471 (4)
H6	0.499634	0.356797	0.761194	0.056*
C16	0.3594 (2)	0.46567 (14)	0.64780 (14)	0.0506 (4)
H7	0.378473	0.539410	0.661815	0.061*
C17	0.2593 (2)	0.46490 (14)	0.56784 (13)	0.0478 (4)
C18	0.2344 (2)	0.35441 (16)	0.54666 (14)	0.0506 (4)
H8	0.168538	0.353381	0.491619	0.061*
C19	0.3064 (2)	0.24558 (14)	0.60666 (12)	0.0423 (3)
H9	0.288535	0.171768	0.591792	0.051*
C20	0.1897 (3)	0.68441 (18)	0.5279 (2)	0.0792 (6)
H12	0.134892	0.699323	0.606260	0.119*
H13	0.127714	0.747593	0.478338	0.119*
H14	0.312930	0.685832	0.515177	0.119*
N1	0.99246 (18)	0.06727 (16)	0.73010 (13)	0.0548 (4)
H11	1.045 (3)	0.044 (2)	0.664 (2)	0.082*
H10	1.050 (3)	0.0795 (18)	0.7738 (17)	0.063 (6)*
N2	0.7914 (2)	0.00034 (16)	0.50810 (12)	0.0636 (4)
O1	0.15733 (14)	0.14244 (11)	0.91391 (10)	0.0554 (3)
O2	0.25831 (14)	0.17565 (10)	1.06096 (8)	0.0469 (3)
O3	0.76834 (13)	0.13240 (10)	0.87243 (8)	0.0438 (3)
O4	0.18023 (18)	0.56733 (12)	0.50445 (12)	0.0718 (4)
C21	0.7402 (3)	0.47407 (18)	0.9117 (2)	0.0699 (5)
C22	0.9237 (4)	0.4564 (3)	0.8413 (3)	0.1178 (10)
H16	0.917608	0.462359	0.761649	0.177*
H17	0.974923	0.519298	0.855137	0.177*
H18	0.997116	0.376303	0.861655	0.177*
O5	0.6192 (2)	0.4549 (2)	0.87859 (14)	0.1048 (6)
O6	0.7183 (3)	0.51493 (19)	1.01024 (16)	0.0988 (6)
H15	0.594 (5)	0.518 (3)	1.052 (3)	0.139 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0345 (7)	0.0454 (7)	0.0371 (7)	−0.0108 (6)	−0.0012 (6)	−0.0037 (5)
C2	0.0324 (7)	0.0380 (6)	0.0312 (6)	−0.0091 (5)	−0.0030 (5)	−0.0035 (5)
C3	0.0335 (7)	0.0403 (7)	0.0302 (6)	−0.0096 (6)	−0.0023 (5)	−0.0047 (5)
C4	0.0451 (8)	0.0401 (7)	0.0304 (6)	−0.0095 (6)	−0.0066 (6)	−0.0051 (5)
C5	0.0478 (9)	0.0398 (7)	0.0337 (7)	−0.0098 (6)	−0.0024 (6)	−0.0032 (5)
C6	0.0531 (10)	0.0607 (9)	0.0406 (8)	−0.0132 (8)	−0.0120 (7)	−0.0119 (7)
C7	0.0770 (13)	0.0790 (12)	0.0458 (9)	−0.0182 (10)	−0.0217 (9)	−0.0178 (8)
C8	0.0889 (15)	0.0741 (11)	0.0341 (8)	−0.0165 (11)	−0.0079 (9)	−0.0174 (8)
C9	0.0674 (11)	0.0580 (9)	0.0369 (7)	−0.0129 (8)	0.0051 (7)	−0.0104 (7)
C10	0.0343 (7)	0.0459 (7)	0.0304 (6)	−0.0098 (6)	−0.0025 (5)	−0.0073 (5)
C11	0.0342 (7)	0.0404 (7)	0.0303 (6)	−0.0107 (6)	−0.0018 (5)	−0.0072 (5)
C12	0.0321 (7)	0.0398 (6)	0.0321 (6)	−0.0123 (6)	−0.0054 (5)	−0.0060 (5)
C13	0.0351 (8)	0.0517 (8)	0.0395 (7)	−0.0145 (6)	−0.0022 (6)	−0.0121 (6)
C14	0.0307 (7)	0.0434 (7)	0.0301 (6)	−0.0105 (6)	−0.0044 (5)	−0.0058 (5)
C15	0.0541 (9)	0.0471 (8)	0.0470 (8)	−0.0148 (7)	−0.0214 (7)	−0.0051 (6)
C16	0.0561 (10)	0.0423 (7)	0.0578 (9)	−0.0149 (7)	−0.0172 (8)	−0.0039 (6)
C17	0.0379 (8)	0.0505 (8)	0.0515 (8)	−0.0089 (7)	−0.0104 (7)	0.0051 (7)
C18	0.0455 (9)	0.0646 (10)	0.0477 (8)	−0.0164 (8)	−0.0222 (7)	0.0009 (7)
C19	0.0402 (8)	0.0517 (8)	0.0412 (7)	−0.0179 (7)	−0.0113 (6)	−0.0064 (6)
C20	0.0751 (14)	0.0545 (10)	0.1034 (16)	−0.0150 (10)	−0.0250 (12)	0.0192 (10)
N1	0.0308 (7)	0.0912 (11)	0.0429 (7)	−0.0141 (7)	−0.0023 (6)	−0.0193 (7)
N2	0.0572 (9)	0.0925 (11)	0.0472 (8)	−0.0284 (8)	0.0044 (7)	−0.0316 (7)
O1	0.0353 (6)	0.0801 (8)	0.0527 (6)	−0.0193 (6)	−0.0039 (5)	−0.0101 (6)
O2	0.0403 (6)	0.0604 (6)	0.0357 (5)	−0.0130 (5)	0.0036 (4)	−0.0076 (4)
O3	0.0319 (5)	0.0684 (7)	0.0334 (5)	−0.0147 (5)	−0.0026 (4)	−0.0144 (4)
O4	0.0689 (9)	0.0603 (7)	0.0882 (9)	−0.0144 (6)	−0.0377 (7)	0.0201 (6)
C21	0.0617 (13)	0.0648 (11)	0.0844 (14)	−0.0198 (10)	−0.0065 (11)	−0.0153 (10)
C22	0.0723 (17)	0.126 (2)	0.137 (3)	−0.0156 (16)	0.0149 (16)	−0.0281 (19)
O5	0.0846 (12)	0.1625 (17)	0.0870 (11)	−0.0550 (12)	0.0017 (9)	−0.0599 (11)
O6	0.0784 (12)	0.1447 (16)	0.0913 (12)	−0.0462 (11)	−0.0156 (10)	−0.0361 (11)

Geometric parameters (Å, º) top

C2—C1	1.4459 (19)	C18—H8	0.9300
C2—C3	1.3435 (19)	C18—C19	1.380 (2)
C3—C4	1.4439 (18)	C19—C14	1.3834 (19)
C4—C6	1.396 (2)	C19—H9	0.9300
C5—C4	1.387 (2)	C20—H12	0.9600
C5—C9	1.389 (2)	C20—H13	0.9600
C6—H4	0.9300	C20—H14	0.9600
C7—C6	1.377 (2)	N1—C10	1.3339 (19)
C7—H3	0.9300	N1—H11	0.85 (2)
C8—C7	1.378 (3)	N1—H10	0.81 (2)
C8—H2	0.9300	N2—C13	1.1416 (18)
C9—C8	1.374 (3)	O1—C1	1.2072 (17)
C9—H1	0.9300	O2—C1	1.3776 (17)
C11—C10	1.3529 (19)	O2—C5	1.3753 (18)
C11—C13	1.4161 (18)	O3—C3	1.3608 (16)
C12—C2	1.5075 (17)	O3—C10	1.3718 (15)
C12—C11	1.5165 (18)	O4—C17	1.3691 (18)
C12—H5	0.9800	O4—C20	1.414 (2)
C14—C12	1.5253 (18)	C22—C21	1.488 (3)
C14—C15	1.380 (2)	C22—H16	0.9600
C15—H6	0.9300	C22—H17	0.9600
C15—C16	1.385 (2)	C22—H18	0.9600
C16—H7	0.9300	O5—C21	1.197 (3)
C17—C16	1.375 (2)	O6—C21	1.284 (3)
C17—C18	1.381 (2)	O6—H15	1.00 (4)

O1—C1—C2	125.22 (13)	C15—C14—C12	120.49 (12)
O1—C1—O2	116.85 (13)	C15—C14—C19	118.23 (13)
O2—C1—C2	117.93 (12)	C19—C14—C12	121.21 (12)
C1—C2—C12	118.49 (12)	C14—C15—H6	119.2
C3—C2—C1	119.38 (12)	C14—C15—C16	121.51 (13)
C3—C2—C12	122.09 (12)	C16—C15—H6	119.2
C2—C3—C4	122.65 (13)	C15—C16—H7	120.2
C2—C3—O3	123.72 (11)	C17—C16—C15	119.55 (14)
O3—C3—C4	113.62 (12)	C17—C16—H7	120.2
C5—C4—C3	116.32 (13)	C16—C17—C18	119.60 (14)
C5—C4—C6	119.71 (13)	O4—C17—C16	124.86 (15)
C6—C4—C3	123.98 (14)	O4—C17—C18	115.54 (14)
C4—C5—C9	120.82 (15)	C17—C18—H8	119.8
O2—C5—C4	121.65 (12)	C19—C18—C17	120.42 (13)
O2—C5—C9	117.52 (14)	C19—C18—H8	119.8
C4—C6—H4	120.5	C14—C19—H9	119.7
C7—C6—C4	119.07 (16)	C18—C19—C14	120.67 (13)
C7—C6—H4	120.5	C18—C19—H9	119.7
C6—C7—H3	119.7	H12—C20—H13	109.5
C6—C7—C8	120.64 (17)	H12—C20—H14	109.5
C8—C7—H3	119.7	H13—C20—H14	109.5
C7—C8—H2	119.4	O4—C20—H12	109.5
C9—C8—C7	121.17 (15)	O4—C20—H13	109.5
C9—C8—H2	119.4	O4—C20—H14	109.5
C5—C9—H1	120.7	C10—N1—H11	122.0 (16)
C8—C9—C5	118.59 (17)	C10—N1—H10	117.6 (14)
C8—C9—H1	120.7	H11—N1—H10	120 (2)
C11—C10—O3	121.49 (12)	C5—O2—C1	121.99 (11)
N1—C10—C11	129.17 (13)	C3—O3—C10	118.34 (11)
N1—C10—O3	109.34 (12)	C17—O4—C20	118.28 (15)
C10—C11—C12	123.19 (11)	O5—C21—C22	123.0 (2)
C10—C11—C13	118.66 (12)	O5—C21—O6	121.7 (2)
C13—C11—C12	117.94 (12)	O6—C21—C22	115.3 (2)
C2—C12—C11	107.92 (10)	C21—C22—H16	109.5
C2—C12—H5	108.6	C21—C22—H17	109.5
C2—C12—C14	111.51 (10)	C21—C22—H18	109.5
C11—C12—H5	108.6	H17—C22—H16	109.5
C11—C12—C14	111.56 (10)	H18—C22—H16	109.5
C14—C12—H5	108.6	H18—C22—H17	109.5
N2—C13—C11	178.91 (16)	C21—O6—H15	108.3 (19)

C1—C2—C3—C4	−2.4 (2)	C12—C11—C10—N1	−173.68 (14)
C1—C2—C3—O3	178.15 (12)	C12—C11—C10—O3	6.6 (2)
C1—O2—C5—C4	−1.4 (2)	C12—C14—C15—C16	178.31 (14)
C1—O2—C5—C9	179.66 (13)	C13—C11—C10—N1	1.0 (2)
C2—C3—C4—C5	0.2 (2)	C13—C11—C10—O3	−178.68 (12)
C2—C3—C4—C6	−179.69 (13)	C14—C12—C2—C1	71.60 (15)
C2—C12—C11—C10	−18.04 (17)	C14—C12—C2—C3	−106.15 (14)
C2—C12—C11—C13	167.21 (11)	C14—C12—C11—C10	104.78 (14)
C3—C2—C1—O1	−176.40 (14)	C14—C12—C11—C13	−69.97 (15)
C3—C2—C1—O2	2.84 (19)	C14—C15—C16—C17	−0.2 (3)
C3—C4—C6—C7	179.99 (14)	C15—C14—C12—C2	47.04 (17)
C3—O3—C10—C11	8.62 (19)	C15—C14—C12—C11	−73.70 (16)
C3—O3—C10—N1	−171.14 (12)	C16—C17—C18—C19	1.2 (3)
C4—C5—C9—C8	−0.7 (2)	C17—C18—C19—C14	−0.1 (2)
C5—C4—C6—C7	0.2 (2)	C18—C17—C16—C15	−1.0 (3)
C5—C9—C8—C7	0.0 (3)	C18—C19—C14—C12	−178.09 (13)
C5—O2—C1—C2	−0.99 (19)	C18—C19—C14—C15	−1.0 (2)
C5—O2—C1—O1	178.31 (12)	C19—C14—C12—C2	−135.97 (13)
C8—C7—C6—C4	−0.8 (3)	C19—C14—C12—C11	103.28 (14)
C9—C5—C4—C3	−179.26 (12)	C19—C14—C15—C16	1.2 (2)
C9—C5—C4—C6	0.6 (2)	C20—O4—C17—C16	−5.0 (3)
C9—C8—C7—C6	0.8 (3)	C20—O4—C17—C18	175.46 (17)
C10—O3—C3—C2	−10.0 (2)	O2—C5—C4—C3	1.79 (19)
C10—O3—C3—C4	170.56 (11)	O2—C5—C4—C6	−178.36 (13)
C11—C12—C2—C1	−165.55 (11)	O2—C5—C9—C8	178.34 (14)
C11—C12—C2—C3	16.70 (17)	O3—C3—C4—C5	179.61 (12)
C12—C2—C1—O1	5.8 (2)	O3—C3—C4—C6	−0.2 (2)
C12—C2—C1—O2	−174.98 (11)	O4—C17—C16—C15	179.48 (15)
C12—C2—C3—C4	175.29 (11)	O4—C17—C18—C19	−179.25 (14)
C12—C2—C3—O3	−4.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2ⁱ	0.85 (2)	2.22 (2)	3.062 (2)	172 (2)
N1—H10···O1ⁱⁱ	0.81 (2)	2.31 (2)	3.111 (2)	168 (2)
O6—H15···O5ⁱⁱⁱ	1.00 (4)	1.67 (4)	2.664 (3)	172 (3)
C15—H6···O5	0.93	2.39	3.251 (2)	154

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

Acknowledgements

The authors gratefully acknowledge DST–FIST (Chemistry Department) of Assam University and USIC, Gauhati University, India, for recording of the X-ray data.

Funding information

Funding for this research was provided by: Department of Science and Technology, Ministry of Science and Technology, India (scholarship No. INSPIRE to Saurav Paul); University Grants Commission (scholarship to Bimal Bhushan Chakraborty); Department of Science and Technology, Ministry of Science and Technology, India, Science and Engineering Research Board (grant to Sudip Choudhury).

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