2-(2,4-Di­nitro­phen­yl)-1-(pyridin-4-yl)ethanol monohydrate

Huang, H.; Wu, Z.

doi:10.1107/S2414314620016405

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 2| February 2021| x201640

https://doi.org/10.1107/S2414314620016405

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2-(2,4-Dinitrophenyl)-1-(pyridin-4-yl)ethanol monohydrate

Houshi Huang ^a and Zhichao Wu ^a ^*

^aDepartment of Chemistry, Anhui University, Hefei, Anhui 230039, People's Republic of China
^*Correspondence e-mail: wu_zhichao63@sina.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 December 2020; accepted 18 December 2020; online 2 February 2021)

In the title compound, C₁₃H₁₁N₃O₅·H₂O, the dihedral angle between the aromatic rings is 9.60 (7)° and the chain linking the rings has an anti conformation with a torsion angle of −178.28 (12)°. In the crystal, the components are linked by O—H⋯O and O—H⋯N hydrogen bonds, generating (010) sheets.

Keywords: crystal structure; dihedral angle; hydrogen bonds; layered structure.

CCDC reference: 2047186

Structure description

Pyridine derivatives have been widely used in biochemistry. Pyridine salts, for example, are well known for their photoactivity and exhibit potential for targetting mitochondria and in the photodynamic therapy of diseases (Wang et al., 2020 ; Li et al.,2017 ). The Knoevenagel reaction is one of the most efficient methods of constructing pyridine-containing organic semiconductors though a two-step process: (1) format the hydroxyl-containing intermediates; (2) obtain products by a dehydration reaction. We report here the of the title compound, C₁₃H₁₁N₃O₅·H₂O (Fig. 1), a hydroxyl-containing intermediate. The dihedral angle between the benzene and pyridine rings is 9.60 (7)° and the chain linking the rings has an anti conformation with a C5—C11—C18—C6 torsion angle of −178.28 (12)°. In the crystal, the components are linked by O—H⋯O and O—H⋯N hydrogen bonds (Table 1), generating (010) sheets.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.80 (2)	2.01 (2)	2.801 (3)	173 (2)
O1—H1B⋯N10ⁱⁱ	0.86 (3)	2.00 (3)	2.841 (3)	166.1 (19)
O2—H2⋯O1ⁱⁱⁱ	0.82	1.85	2.666 (3)	175
C17—H17⋯O20^iv	0.93	2.53	3.226 (4)	131
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound showing 50% displacement ellipsoids.

Synthesis and crystallization

1-Methyl-2,4-dinitro-benzene (0.546 g, 3.00 mmol) and pyridine-4-carbaldehyde (0.321 g, 3.00 mmol) were dissolved in dimethyl sulfoxide (50 ml). The mixture was heated to 80°C for 4 h, then cooled to room temperature and poured into water. The precipitate was collected by filtration and dried to obtain a yellow solid (0.712 g, 2.4 mol). Yellow crystals suitable for X-ray analysis were obtained by recrystallization from ethanol solution.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₅·H₂O
M_r	307.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.639 (8), 20.045 (12), 8.116 (5)
β (°)	101.326 (5)
V (Å³)	1378.2 (17)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.19 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.616, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10488, 2889, 2531
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.645

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.03
No. of reflections	2889
No. of parameters	208
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24
Computer programs: SMART and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ) and SHELXTL (Sheldrick, 2008).

Structural data

CCDC reference: 2047186

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016405/hb4371sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016405/hb4371Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620016405/hb4371Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

2-(2,4-Dinitrophenyl)-1-(pyridin-4-yl)ethanol monohydrate top

Crystal data top

C₁₃H₁₁N₃O₅·H₂O	F(000) = 640
M_r = 307.26	D_x = 1.481 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.639 (8) Å	Cell parameters from 6924 reflections
b = 20.045 (12) Å	θ = 2.6–27.1°
c = 8.116 (5) Å	µ = 0.12 mm⁻¹
β = 101.326 (5)°	T = 296 K
V = 1378.2 (17) Å³	Block, yellow
Z = 4	0.19 × 0.18 × 0.17 mm

Data collection top

Bruker SMART CCD diffractometer	2531 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.025
ω scans	θ_max = 27.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.616, T_max = 0.746	k = −22→25
10488 measured reflections	l = −10→10
2889 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0605P)² + 0.4306P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2889 reflections	Δρ_max = 0.37 e Å⁻³
208 parameters	Δρ_min = −0.24 e Å⁻³
0 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
O2	0.11854 (12)	0.30340 (6)	0.04733 (14)	0.0475 (3)
H2	0.0856	0.3009	−0.0544	0.071*
C3	−0.03252 (17)	0.51894 (7)	0.25550 (18)	0.0418 (3)
H3	−0.0432	0.5644	0.2332	0.050*
C4	0.10032 (16)	0.48431 (7)	0.23286 (18)	0.0389 (3)
C5	0.40549 (16)	0.30336 (7)	0.08026 (17)	0.0383 (3)
C6	0.12367 (17)	0.41637 (7)	0.26901 (17)	0.0393 (3)
C7	−0.14831 (17)	0.48357 (8)	0.31235 (18)	0.0435 (3)
N8	−0.29271 (16)	0.51917 (8)	0.33273 (18)	0.0563 (4)
N9	0.21854 (15)	0.52431 (6)	0.16714 (18)	0.0500 (3)
N10	0.68428 (15)	0.23063 (7)	0.09129 (19)	0.0534 (4)
C11	0.25687 (16)	0.34380 (7)	0.07980 (18)	0.0394 (3)
H11	0.2482	0.3787	−0.0060	0.047*
O12	0.30318 (16)	0.49757 (7)	0.08429 (19)	0.0669 (4)
C13	0.41333 (17)	0.23595 (7)	0.1180 (2)	0.0451 (3)
H13	0.3254	0.2137	0.1408	0.054*
O14	−0.30398 (18)	0.57810 (8)	0.2980 (2)	0.0795 (4)
C15	0.0034 (2)	0.38446 (8)	0.3309 (2)	0.0488 (4)
H15	0.0154	0.3396	0.3594	0.059*
C16	−0.1328 (2)	0.41660 (8)	0.3516 (2)	0.0504 (4)
H16	−0.2119	0.3937	0.3910	0.060*
C17	0.55312 (19)	0.20209 (8)	0.1213 (2)	0.0529 (4)
H17	0.5560	0.1567	0.1459	0.064*
C18	0.26799 (18)	0.37632 (7)	0.25304 (19)	0.0438 (3)
H18A	0.2839	0.3417	0.3382	0.053*
H18B	0.3596	0.4054	0.2747	0.053*
C19	0.54071 (18)	0.33341 (8)	0.0472 (2)	0.0499 (4)
H19	0.5407	0.3785	0.0205	0.060*
O20	0.2244 (2)	0.58322 (7)	0.1986 (3)	0.1047 (7)
C21	0.67505 (19)	0.29564 (9)	0.0543 (2)	0.0547 (4)
H21	0.7647	0.3166	0.0320	0.066*
O22	−0.3925 (2)	0.48738 (9)	0.3855 (3)	0.1002 (6)
O1	−0.00579 (15)	0.69790 (7)	0.28295 (16)	0.0537 (3)
H1A	−0.044 (3)	0.7282 (11)	0.324 (3)	0.072 (7)*
H1B	0.094 (3)	0.7007 (10)	0.319 (3)	0.072 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0343 (5)	0.0568 (6)	0.0508 (6)	−0.0054 (4)	0.0066 (4)	−0.0012 (5)
C3	0.0400 (7)	0.0391 (7)	0.0445 (7)	0.0017 (6)	0.0040 (6)	−0.0014 (6)
C4	0.0356 (7)	0.0387 (7)	0.0413 (7)	−0.0043 (5)	0.0053 (5)	−0.0016 (6)
C5	0.0340 (7)	0.0411 (7)	0.0395 (7)	−0.0008 (5)	0.0064 (5)	−0.0012 (5)
C6	0.0403 (7)	0.0395 (7)	0.0377 (7)	0.0010 (6)	0.0062 (5)	−0.0019 (5)
C7	0.0380 (7)	0.0513 (8)	0.0412 (7)	0.0024 (6)	0.0075 (6)	−0.0072 (6)
N8	0.0428 (7)	0.0717 (10)	0.0559 (8)	0.0063 (7)	0.0134 (6)	−0.0074 (7)
N9	0.0424 (7)	0.0421 (7)	0.0661 (9)	−0.0068 (5)	0.0121 (6)	−0.0001 (6)
N10	0.0366 (7)	0.0576 (8)	0.0659 (9)	0.0065 (6)	0.0094 (6)	0.0050 (7)
C11	0.0337 (7)	0.0408 (7)	0.0433 (7)	0.0001 (5)	0.0065 (5)	0.0032 (6)
O12	0.0645 (8)	0.0615 (8)	0.0841 (9)	−0.0096 (6)	0.0378 (7)	−0.0020 (7)
C13	0.0352 (7)	0.0427 (8)	0.0577 (9)	−0.0029 (6)	0.0095 (6)	0.0028 (6)
O14	0.0669 (9)	0.0698 (9)	0.1059 (12)	0.0257 (7)	0.0271 (8)	0.0022 (8)
C15	0.0599 (9)	0.0382 (7)	0.0521 (8)	−0.0003 (7)	0.0200 (7)	0.0022 (6)
C16	0.0502 (9)	0.0520 (9)	0.0534 (9)	−0.0089 (7)	0.0212 (7)	−0.0031 (7)
C17	0.0424 (8)	0.0441 (8)	0.0718 (11)	0.0034 (6)	0.0100 (7)	0.0057 (7)
C18	0.0423 (8)	0.0433 (8)	0.0442 (8)	0.0061 (6)	0.0049 (6)	0.0004 (6)
C19	0.0407 (8)	0.0444 (8)	0.0661 (10)	−0.0025 (6)	0.0144 (7)	0.0063 (7)
O20	0.0977 (12)	0.0435 (7)	0.193 (2)	−0.0191 (7)	0.0773 (13)	−0.0134 (10)
C21	0.0345 (8)	0.0607 (10)	0.0708 (11)	−0.0036 (7)	0.0149 (7)	0.0058 (8)
O22	0.0645 (9)	0.1094 (13)	0.1428 (17)	0.0092 (9)	0.0599 (11)	0.0136 (12)
O1	0.0379 (6)	0.0607 (8)	0.0601 (7)	−0.0024 (5)	0.0034 (5)	−0.0086 (6)

Geometric parameters (Å, º) top

O2—C11	1.4248 (19)	N10—C17	1.334 (2)
O2—H2	0.8200	N10—C21	1.336 (2)
C3—C7	1.378 (2)	C11—C18	1.536 (2)
C3—C4	1.384 (2)	C11—H11	0.9800
C3—H3	0.9300	C13—C17	1.381 (2)
C4—C6	1.400 (2)	C13—H13	0.9300
C4—N9	1.478 (2)	C15—C16	1.380 (2)
C5—C13	1.384 (2)	C15—H15	0.9300
C5—C19	1.387 (2)	C16—H16	0.9300
C5—C11	1.518 (2)	C17—H17	0.9300
C6—C15	1.395 (2)	C18—H18A	0.9700
C6—C18	1.510 (2)	C18—H18B	0.9700
C7—C16	1.380 (2)	C19—C21	1.377 (2)
C7—N8	1.474 (2)	C19—H19	0.9300
N8—O14	1.214 (2)	C21—H21	0.9300
N8—O22	1.216 (2)	O1—H1A	0.80 (2)
N9—O20	1.207 (2)	O1—H1B	0.86 (3)
N9—O12	1.2113 (19)

C11—O2—H2	109.5	C5—C11—H11	109.3
C7—C3—C4	117.52 (14)	C18—C11—H11	109.3
C7—C3—H3	121.2	C17—C13—C5	119.26 (14)
C4—C3—H3	121.2	C17—C13—H13	120.4
C3—C4—C6	123.32 (13)	C5—C13—H13	120.4
C3—C4—N9	115.20 (13)	C16—C15—C6	122.89 (15)
C6—C4—N9	121.48 (13)	C16—C15—H15	118.6
C13—C5—C19	117.41 (14)	C6—C15—H15	118.6
C13—C5—C11	121.77 (13)	C15—C16—C7	118.20 (14)
C19—C5—C11	120.79 (14)	C15—C16—H16	120.9
C15—C6—C4	115.76 (13)	C7—C16—H16	120.9
C15—C6—C18	118.25 (14)	N10—C17—C13	123.82 (16)
C4—C6—C18	125.94 (13)	N10—C17—H17	118.1
C3—C7—C16	122.26 (14)	C13—C17—H17	118.1
C3—C7—N8	118.34 (15)	C6—C18—C11	113.58 (12)
C16—C7—N8	119.40 (14)	C6—C18—H18A	108.8
O14—N8—O22	124.18 (16)	C11—C18—H18A	108.8
O14—N8—C7	118.42 (15)	C6—C18—H18B	108.8
O22—N8—C7	117.39 (17)	C11—C18—H18B	108.8
O20—N9—O12	123.07 (15)	H18A—C18—H18B	107.7
O20—N9—C4	117.22 (14)	C21—C19—C5	119.22 (15)
O12—N9—C4	119.71 (13)	C21—C19—H19	120.4
C17—N10—C21	116.36 (14)	C5—C19—H19	120.4
O2—C11—C5	112.04 (13)	N10—C21—C19	123.92 (15)
O2—C11—C18	108.06 (12)	N10—C21—H21	118.0
C5—C11—C18	108.88 (11)	C19—C21—H21	118.0
O2—C11—H11	109.3	H1A—O1—H1B	106 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.80 (2)	2.01 (2)	2.801 (3)	173 (2)
O1—H1B···N10ⁱⁱ	0.86 (3)	2.00 (3)	2.841 (3)	166.1 (19)
O2—H2···O1ⁱⁱⁱ	0.82	1.85	2.666 (3)	175
C17—H17···O20^iv	0.93	2.53	3.226 (4)	131

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

Funding information

This work was supported by General Program of National Natural Science Foundation of China (51772002, 21805001, 51432001), Anhui Province Postdoctoral Sustentation Fund (2017B159), the PhD Research Startup Foundation of Anhui Jianzhu University (2016QD109), Anhui Province University Natural Science Research Project (KJ2017A008) and the Anhui Provincial Natural Science Foundation (1808085ME55).

References

Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H., Li, Y., Zhang, H., Xu, G., Zhang, Y., Liu, X., Zhou, H., Yang, X., Zhang, X. & Tian, Y. (2017). Chem. Commun. 53, 13245–13248. Web of Science 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
Wang, J., Zhu, X., Zhang, J., Wang, H., Liu, G., Bu, Y., Yu, J., Tian, Y. & Zhou, H. (2020). Appl. Mater. Interfaces, 12, 1988–1996. Web of Science CrossRef CAS Google Scholar

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