Diethyl 4-(1H-indol-3-yl)-2,6-dimethyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

Lee, J.H.; Koh, D.

doi:10.1107/S2414314619001937

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190193

https://doi.org/10.1107/S2414314619001937

Open

access

Diethyl 4-(1H-indol-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Ji Hye Lee ^a and Dongsoo Koh ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by O. Blacque, University of Zürich, Switzerland (Received 18 January 2019; accepted 3 February 2019; online 8 February 2019)

In the title compound, C₂₁H₂₄N₂O₄, the 1,4-dihydropyridine ring adopts a very flattened boat conformation, with the 3-pyridine substituent in an axial orientation. The pyridine ring is almost orthogonally twisted relative to the 1,4-dihydropyridine skeleton by 85.97 (2)°. In the crystal, pairs of N—H⋯O hydrogen bonds form inversion dimers enclosing R²₂(16) rings. Pairs of intermolecular N—H⋯O hydrogen bonds link the dimers into chains along [100].

Keywords: crystal structure1,4-dihydropyridine; N—H⋯O hydrogen bonds; synthesis.

CCDC reference: 1895315

Structure description

1,4-dihydropyridine (1,4-DHP) derivatives are known as Hantzsch compounds. According to our recent report, they show anti-cancer activities against the HCT116 human colon cancer cell lines (Ahn et al., 2018 ). Their biological activities include anticonvulsant (Prasanthi et al., 2014 ), calcium channel modulator (Budriesi et al., 2005 ), anti-tubercular (Khoshneviszadeh et al., 2009 ) and antimycobacterial activities (Lentz et al., 2016 ).

The molecular structure of the title compound is shown in Fig. 1. The 1,4-dihydropyridine (C1–C5/N1) ring is slightly twisted from planarity, with a maximum deviation of 0.138 (1) Å at C3 (r.m.s. deviation = 0.091 Å). The dihedral angle formed between the plane of the 1,4-dihydropyridine (C1–C5/N1) ring and the indole (C10–C17/N2; r.m.s. deviation = 0.011 Å) ring is 85.97 (2)°. One of the carbonyl groups (C7=O1) lies on the same side of the plane as the methyl group at C6, while the other carbonyl group (C18=O3) lies on the opposite side to the methyl group at C21.

Figure 1
The molecular structure of the title compound, showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability level.

In the crystal structure, pairs of N2—H2⋯O3ⁱⁱ hydrogen bonds form inversion dimers enclosing R²₂(16) rings (Table 1, Fig. 2). The dimers are linked into chains along the a-axis direction by pairs of N1—H1⋯O1ⁱ hydrogen bonds (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.90 (2)	2.18 (2)	3.009 (2)	153 (2)
N2—H2⋯O3ⁱⁱ	0.91 (2)	2.00 (2)	2.906 (3)	173 (3)
C6—H6B⋯O1ⁱ	0.97	2.49	3.296 (3)	140
C13—H13⋯O1ⁱⁱⁱ	0.94	2.58	3.357 (3)	140
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Part of the structure showing a dimer formed by N—H⋯N hydrogen bonds (shown as blue dashed lines).

Figure 3
Part of the crystal structure showing N—H⋯N hydrogen bonds as orange dash lines. For clarity only those H atoms involved in hydrogen bonding are shown.

Synthesis and crystallization

Methyl acetoacetate (20 mmol) and indole-3-carbaldehyde (10 mmol) were dissolved in 30 ml of ethanol to give a clear solution. To the mixture, ammonium acetate (10 mmol) was added and the reaction mixture was heated at 363 K for 2 h. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature to produce a solid product. This solid was recrystallized from ethanol solution to obtain single-crystal of the title the compound in 51% yield.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₄
M_r	368.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	10.6258 (5), 10.2217 (5), 18.0993 (8)
β (°)	90.798 (2)
V (Å³)	1965.64 (16)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.18 × 0.14

Data collection
Diffractometer	PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.686, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	83213, 4908, 3123
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.198, 1.03
No. of reflections	4908
No. of parameters	254
No. of restraints	4
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.48
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1895315

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001937/zq4034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001937/zq4034Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619001937/zq4034Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Diethyl 4-(1H-indol-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₁H₂₄N₂O₄	F(000) = 784
M_r = 368.42	D_x = 1.245 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.6258 (5) Å	Cell parameters from 9897 reflections
b = 10.2217 (5) Å	θ = 2.3–25.4°
c = 18.0993 (8) Å	µ = 0.09 mm⁻¹
β = 90.798 (2)°	T = 223 K
V = 1965.64 (16) Å³	Block, colourless
Z = 4	0.24 × 0.18 × 0.14 mm

Data collection top

PHOTON 100 CMOS diffractometer	3123 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.096
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θ_max = 28.3°, θ_min = 1.9°
T_min = 0.686, T_max = 0.746	h = −14→14
83213 measured reflections	k = −13→13
4908 independent reflections	l = −24→24

Refinement top

Refinement on F²	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.063	H-atom parameters not refined
wR(F²) = 0.198	w = 1/[σ²(F_o²) + (0.087P)² + 1.2621P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4908 reflections	Δρ_max = 0.54 e Å⁻³
254 parameters	Δρ_min = −0.47 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

	x	y	z	U_iso*/U_eq
N1	0.00309 (17)	0.61066 (19)	0.15703 (10)	0.0407 (4)
H1	−0.0613 (19)	0.648 (2)	0.1808 (13)	0.049*
C1	0.04291 (19)	0.4898 (2)	0.18142 (12)	0.0381 (5)
C2	0.13159 (19)	0.4253 (2)	0.14337 (11)	0.0358 (5)
C3	0.19820 (19)	0.4892 (2)	0.07873 (11)	0.0367 (5)
H3	0.2050	0.4229	0.0391	0.044*
C4	0.12181 (19)	0.6032 (2)	0.04792 (11)	0.0375 (5)
C5	0.0307 (2)	0.6611 (2)	0.08802 (12)	0.0394 (5)
C6	−0.0235 (3)	0.4445 (3)	0.24927 (14)	0.0536 (6)
H6A	−0.0521	0.3552	0.2422	0.080*
H6B	−0.0952	0.5007	0.2582	0.080*
H6C	0.0339	0.4482	0.2914	0.080*
C7	0.1697 (2)	0.2926 (2)	0.16465 (12)	0.0401 (5)
O1	0.14621 (16)	0.23585 (17)	0.22188 (10)	0.0525 (5)
O2	0.23841 (17)	0.23580 (16)	0.11138 (9)	0.0528 (5)
C8	0.2857 (3)	0.1066 (3)	0.12725 (17)	0.0689 (8)
H8A	0.2160	0.0440	0.1291	0.083*
H8B	0.3297	0.1059	0.1752	0.083*
C9	0.3752 (5)	0.0696 (5)	0.0667 (2)	0.131 (2)
H9A	0.3319	0.0747	0.0192	0.196*
H9B	0.4051	−0.0190	0.0747	0.196*
H9C	0.4462	0.1293	0.0672	0.196*
C10	0.33057 (19)	0.5307 (2)	0.10047 (11)	0.0366 (5)
C11	0.4375 (2)	0.4691 (3)	0.07841 (13)	0.0443 (5)
H11	0.4394	0.3950	0.0476	0.053*
N2	0.54168 (18)	0.5301 (2)	0.10733 (11)	0.0497 (5)
H2	0.6204 (18)	0.505 (3)	0.0940 (15)	0.060*
C12	0.5038 (2)	0.6340 (3)	0.14898 (12)	0.0434 (5)
C13	0.5751 (2)	0.7250 (3)	0.18868 (14)	0.0569 (7)
H13	0.6635	0.7225	0.1884	0.068*
C14	0.5125 (3)	0.8182 (3)	0.22819 (16)	0.0611 (7)
H14	0.5588	0.8798	0.2559	0.073*
C15	0.3812 (3)	0.8233 (3)	0.22806 (15)	0.0554 (6)
H15	0.3404	0.8879	0.2558	0.067*
C16	0.3107 (2)	0.7345 (2)	0.18760 (13)	0.0455 (5)
H16	0.2223	0.7396	0.1874	0.055*
C17	0.37063 (19)	0.6372 (2)	0.14690 (12)	0.0379 (5)
C18	0.1572 (2)	0.6424 (2)	−0.02674 (13)	0.0434 (5)
O3	0.21205 (15)	0.57075 (19)	−0.06892 (9)	0.0527 (5)
O4	0.1257 (2)	0.76502 (19)	−0.04444 (10)	0.0688 (6)
C19	0.1540 (3)	0.8084 (4)	−0.11777 (17)	0.0840 (10)
H19A	0.0812	0.8548	−0.1390	0.101*
H19B	0.1719	0.7328	−0.1492	0.101*
C20	0.2678 (5)	0.8993 (6)	−0.1152 (3)	0.144 (2)
H20A	0.2520	0.9706	−0.0812	0.215*
H20B	0.2823	0.9343	−0.1642	0.215*
H20C	0.3413	0.8508	−0.0986	0.215*
C21	−0.0505 (3)	0.7756 (3)	0.06674 (15)	0.0557 (7)
H21A	−0.0035	0.8561	0.0740	0.084*
H21B	−0.1248	0.7768	0.0973	0.084*
H21C	−0.0756	0.7680	0.0152	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0359 (9)	0.0443 (11)	0.0421 (10)	0.0035 (8)	0.0093 (8)	−0.0045 (8)
C1	0.0335 (10)	0.0409 (12)	0.0400 (11)	−0.0048 (9)	0.0042 (9)	−0.0035 (9)
C2	0.0310 (10)	0.0386 (11)	0.0380 (11)	−0.0024 (8)	0.0031 (8)	−0.0007 (9)
C3	0.0333 (10)	0.0409 (12)	0.0361 (11)	0.0004 (9)	0.0038 (8)	−0.0014 (9)
C4	0.0308 (10)	0.0453 (12)	0.0362 (11)	−0.0004 (9)	−0.0004 (8)	−0.0025 (9)
C5	0.0349 (11)	0.0415 (12)	0.0417 (11)	0.0006 (9)	−0.0035 (9)	−0.0031 (9)
C6	0.0570 (15)	0.0502 (14)	0.0542 (14)	−0.0020 (12)	0.0224 (12)	−0.0021 (12)
C7	0.0323 (10)	0.0420 (12)	0.0461 (12)	−0.0039 (9)	0.0041 (9)	−0.0024 (10)
O1	0.0498 (10)	0.0510 (10)	0.0570 (10)	0.0044 (8)	0.0163 (8)	0.0125 (8)
O2	0.0616 (11)	0.0435 (9)	0.0536 (10)	0.0114 (8)	0.0154 (8)	0.0003 (8)
C8	0.079 (2)	0.0482 (16)	0.080 (2)	0.0195 (14)	0.0211 (16)	0.0032 (14)
C9	0.166 (5)	0.105 (3)	0.123 (3)	0.075 (3)	0.057 (3)	0.013 (3)
C10	0.0309 (10)	0.0454 (12)	0.0335 (10)	0.0019 (9)	0.0050 (8)	0.0062 (9)
C11	0.0351 (11)	0.0564 (14)	0.0414 (12)	0.0046 (10)	0.0052 (9)	0.0003 (11)
N2	0.0293 (9)	0.0713 (14)	0.0486 (11)	0.0064 (9)	0.0059 (8)	−0.0001 (10)
C12	0.0322 (11)	0.0590 (14)	0.0392 (11)	0.0001 (10)	0.0037 (9)	0.0073 (10)
C13	0.0368 (12)	0.0796 (19)	0.0540 (14)	−0.0115 (13)	−0.0055 (11)	0.0054 (14)
C14	0.0548 (16)	0.0669 (18)	0.0614 (16)	−0.0131 (14)	−0.0099 (13)	−0.0080 (14)
C15	0.0530 (15)	0.0546 (15)	0.0586 (15)	−0.0028 (12)	−0.0026 (12)	−0.0103 (12)
C16	0.0387 (12)	0.0481 (13)	0.0498 (13)	0.0004 (10)	0.0002 (10)	−0.0027 (11)
C17	0.0318 (10)	0.0455 (12)	0.0365 (10)	−0.0004 (9)	0.0016 (8)	0.0070 (9)
C18	0.0360 (11)	0.0508 (14)	0.0432 (12)	−0.0003 (10)	−0.0059 (9)	0.0014 (11)
O3	0.0418 (9)	0.0740 (12)	0.0424 (9)	0.0091 (8)	0.0071 (7)	0.0025 (8)
O4	0.1006 (16)	0.0565 (12)	0.0496 (11)	0.0063 (11)	0.0064 (10)	0.0113 (9)
C19	0.123 (3)	0.077 (2)	0.0526 (17)	−0.005 (2)	−0.0008 (18)	0.0205 (16)
C20	0.187 (5)	0.153 (5)	0.092 (3)	−0.089 (4)	0.022 (3)	0.004 (3)
C21	0.0513 (14)	0.0575 (16)	0.0581 (15)	0.0149 (12)	−0.0031 (12)	−0.0005 (13)

Geometric parameters (Å, º) top

N1—C1	1.376 (3)	C11—N2	1.368 (3)
N1—C5	1.387 (3)	C11—H11	0.9400
N1—H1	0.899 (16)	N2—C12	1.366 (3)
C1—C2	1.348 (3)	N2—H2	0.911 (17)
C1—C6	1.498 (3)	C12—C13	1.393 (4)
C2—C7	1.465 (3)	C12—C17	1.416 (3)
C2—C3	1.523 (3)	C13—C14	1.369 (4)
C3—C10	1.516 (3)	C13—H13	0.9400
C3—C4	1.521 (3)	C14—C15	1.396 (4)
C3—H3	0.9900	C14—H14	0.9400
C4—C5	1.354 (3)	C15—C16	1.381 (3)
C4—C18	1.463 (3)	C15—H15	0.9400
C5—C21	1.501 (3)	C16—C17	1.397 (3)
C6—H6A	0.9700	C16—H16	0.9400
C6—H6B	0.9700	C18—O3	1.213 (3)
C6—H6C	0.9700	C18—O4	1.335 (3)
C7—O1	1.216 (3)	O4—C19	1.435 (3)
C7—O2	1.349 (3)	C19—C20	1.5250 (19)
O2—C8	1.440 (3)	C19—H19A	0.9800
C8—C9	1.509 (3)	C19—H19B	0.9800
C8—H8A	0.9800	C20—H20A	0.9700
C8—H8B	0.9800	C20—H20B	0.9700
C9—H9A	0.9700	C20—H20C	0.9700
C9—H9B	0.9700	C21—H21A	0.9700
C9—H9C	0.9700	C21—H21B	0.9700
C10—C11	1.364 (3)	C21—H21C	0.9700
C10—C17	1.436 (3)

C1—N1—C5	123.70 (18)	C10—C11—N2	110.5 (2)
C1—N1—H1	117.4 (16)	C10—C11—H11	124.7
C5—N1—H1	116.5 (16)	N2—C11—H11	124.7
C2—C1—N1	119.32 (19)	C12—N2—C11	108.83 (19)
C2—C1—C6	127.5 (2)	C12—N2—H2	130.1 (18)
N1—C1—C6	113.22 (19)	C11—N2—H2	120.7 (18)
C1—C2—C7	120.77 (19)	N2—C12—C13	129.9 (2)
C1—C2—C3	121.2 (2)	N2—C12—C17	107.8 (2)
C7—C2—C3	117.99 (18)	C13—C12—C17	122.3 (2)
C10—C3—C4	111.69 (18)	C14—C13—C12	118.0 (2)
C10—C3—C2	111.10 (17)	C14—C13—H13	121.0
C4—C3—C2	111.04 (17)	C12—C13—H13	121.0
C10—C3—H3	107.6	C13—C14—C15	121.2 (3)
C4—C3—H3	107.6	C13—C14—H14	119.4
C2—C3—H3	107.6	C15—C14—H14	119.4
C5—C4—C18	124.7 (2)	C16—C15—C14	120.8 (3)
C5—C4—C3	121.34 (19)	C16—C15—H15	119.6
C18—C4—C3	113.93 (18)	C14—C15—H15	119.6
C4—C5—N1	118.8 (2)	C15—C16—C17	120.0 (2)
C4—C5—C21	128.0 (2)	C15—C16—H16	120.0
N1—C5—C21	113.2 (2)	C17—C16—H16	120.0
C1—C6—H6A	109.5	C16—C17—C12	117.7 (2)
C1—C6—H6B	109.5	C16—C17—C10	135.6 (2)
H6A—C6—H6B	109.5	C12—C17—C10	106.63 (19)
C1—C6—H6C	109.5	O3—C18—O4	122.4 (2)
H6A—C6—H6C	109.5	O3—C18—C4	123.2 (2)
H6B—C6—H6C	109.5	O4—C18—C4	114.3 (2)
O1—C7—O2	121.5 (2)	C18—O4—C19	117.2 (2)
O1—C7—C2	127.3 (2)	O4—C19—C20	109.6 (3)
O2—C7—C2	111.17 (19)	O4—C19—H19A	109.7
C7—O2—C8	116.30 (19)	C20—C19—H19A	109.7
O2—C8—C9	107.9 (3)	O4—C19—H19B	109.7
O2—C8—H8A	110.1	C20—C19—H19B	109.7
C9—C8—H8A	110.1	H19A—C19—H19B	108.2
O2—C8—H8B	110.1	C19—C20—H20A	109.5
C9—C8—H8B	110.1	C19—C20—H20B	109.5
H8A—C8—H8B	108.4	H20A—C20—H20B	109.5
C8—C9—H9A	109.5	C19—C20—H20C	109.5
C8—C9—H9B	109.5	H20A—C20—H20C	109.5
H9A—C9—H9B	109.5	H20B—C20—H20C	109.5
C8—C9—H9C	109.5	C5—C21—H21A	109.5
H9A—C9—H9C	109.5	C5—C21—H21B	109.5
H9B—C9—H9C	109.5	H21A—C21—H21B	109.5
C11—C10—C17	106.24 (19)	C5—C21—H21C	109.5
C11—C10—C3	124.7 (2)	H21A—C21—H21C	109.5
C17—C10—C3	129.07 (19)	H21B—C21—H21C	109.5

C5—N1—C1—C2	12.5 (3)	C4—C3—C10—C17	51.8 (3)
C5—N1—C1—C6	−166.3 (2)	C2—C3—C10—C17	−72.8 (3)
N1—C1—C2—C7	−175.62 (19)	C17—C10—C11—N2	−0.4 (3)
C6—C1—C2—C7	3.0 (4)	C3—C10—C11—N2	180.0 (2)
N1—C1—C2—C3	6.4 (3)	C10—C11—N2—C12	−0.2 (3)
C6—C1—C2—C3	−175.0 (2)	C11—N2—C12—C13	−179.6 (2)
C1—C2—C3—C10	104.3 (2)	C11—N2—C12—C17	0.8 (3)
C7—C2—C3—C10	−73.7 (2)	N2—C12—C13—C14	−177.9 (3)
C1—C2—C3—C4	−20.7 (3)	C17—C12—C13—C14	1.6 (4)
C7—C2—C3—C4	161.33 (18)	C12—C13—C14—C15	−0.8 (4)
C10—C3—C4—C5	−105.6 (2)	C13—C14—C15—C16	−0.3 (4)
C2—C3—C4—C5	19.0 (3)	C14—C15—C16—C17	0.8 (4)
C10—C3—C4—C18	73.9 (2)	C15—C16—C17—C12	−0.1 (3)
C2—C3—C4—C18	−161.51 (18)	C15—C16—C17—C10	179.2 (2)
C18—C4—C5—N1	177.33 (19)	N2—C12—C17—C16	178.5 (2)
C3—C4—C5—N1	−3.2 (3)	C13—C12—C17—C16	−1.1 (3)
C18—C4—C5—C21	−1.1 (4)	N2—C12—C17—C10	−1.1 (2)
C3—C4—C5—C21	178.4 (2)	C13—C12—C17—C10	179.3 (2)
C1—N1—C5—C4	−14.2 (3)	C11—C10—C17—C16	−178.5 (3)
C1—N1—C5—C21	164.4 (2)	C3—C10—C17—C16	1.1 (4)
C1—C2—C7—O1	−13.3 (4)	C11—C10—C17—C12	0.9 (2)
C3—C2—C7—O1	164.7 (2)	C3—C10—C17—C12	−179.5 (2)
C1—C2—C7—O2	167.0 (2)	C5—C4—C18—O3	−159.2 (2)
C3—C2—C7—O2	−15.0 (3)	C3—C4—C18—O3	21.3 (3)
O1—C7—O2—C8	−2.1 (3)	C5—C4—C18—O4	21.9 (3)
C2—C7—O2—C8	177.6 (2)	C3—C4—C18—O4	−157.6 (2)
C7—O2—C8—C9	−171.5 (3)	O3—C18—O4—C19	3.1 (4)
C4—C3—C10—C11	−128.8 (2)	C4—C18—O4—C19	−178.0 (2)
C2—C3—C10—C11	106.7 (2)	C18—O4—C19—C20	−104.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.90 (2)	2.18 (2)	3.009 (2)	153 (2)
N2—H2···O3ⁱⁱ	0.91 (2)	2.00 (2)	2.906 (3)	173 (3)
C6—H6B···O1ⁱ	0.97	2.49	3.296 (3)	140
C13—H13···O1ⁱⁱⁱ	0.94	2.58	3.357 (3)	140

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

Funding information

The authors acknowledge financial support from the Basic Science Research Program (award No. NRF– 2016R1D1A1B03931623).

References

Ahn, S., Lee, Y., Park, J., Lee, J., Shin, S. Y., Lee, Y. H., Koh, D. & Lim, Y. (2018). Med. Chem. 14, 851–862. CrossRef CAS Google Scholar
Bruker (2012). APEX2, SAINT and SADABS, Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Budriesi, R., Bisi, A., Ioan, P., Rampa, A., Gobbi, S., Belluti, F., Piazzi, L., Valenti, P. & Chiarini, A. (2005). Bioorg. Med. Chem. 13, 3423–3430. CrossRef CAS Google Scholar
Khoshneviszadeh, M., Edraki, N., Javidnia, K., Alborzi, A., Pourabbas, B., Mardaneh, J. & Miri, R. (2009). Bioorg. Med. Chem. 17, 1579–1586. CrossRef CAS Google Scholar
Lentz, F., Hemmer, M., Reiling, N. & Hilgeroth, A. (2016). Bioorg. Med. Chem. Lett. 26, 5896–5898. CrossRef CAS Google Scholar
Prasanthi, G., Prasad, K. V. S. R. G. & Bharathi, K. (2014). Eur. J. Med. Chem. 73, 97–104. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals 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.