Crystal structure and Hirshfeld surface analysis of (E)-2-[1-hy­droxy-2-(pyridin-2-yl)eth­yl]-4-[2-(4-meth­oxy­phen­yl)diazen-1-yl]phenol

Faizi, M.S.H.; Sen, P.; Saxena, G.K.; Golenya, I.A.

doi:10.1107/S2056989019004377

Crystal structure and Hirshfeld surface analysis of (E)-2-[1-hydroxy-2-(pyridin-2-yl)ethyl]-4-[2-(4-methoxyphenyl)diazen-1-yl]phenol

M. S. H. Faizi, P. Sen, G. K. Saxena and I. A. Golenya

In the title compound, the configuration about the N=N bond is E, and the central benzene ring is inclined to the pyridine ring by 31. 43 (8)° and to the 4-methoxyphenyl ring by 4.73 (8)°. In the crystal, molecules are linked by pairs of O—H

N hydrogen bonds, forming inversion dimers with an $R_{2}^{2}$ (12) ring motif.

Keywords: crystal structure; azo compounds; diazenyl; pyridine; hydrogen bonding; C—H

π interactions; offset π–π interactions; supramolecular framework; Hirshfeld surface analysis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019004377/su5489sup1.cif Contains datablocks I, Global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019004377/su5489Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019004377/su5489Isup3.cml Supplementary material

CCDC reference: 959013

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.100
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2       --C10      .        5.5 s.u.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.122 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)      0.005 Ang.
PLAT793_ALERT_4_G Model has Chirality at C7          (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-2-[1-Hydroxy-2-(pyridin-2-yl)ethyl]-4-[2-(4-methoxyphenyl)diazen-1-yl]phenol top

Crystal data top

C₂₀H₁₉N₃O₃	F(000) = 736
M_r = 349.38	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.451 (5) Å	Cell parameters from 1490 reflections
b = 8.169 (5) Å	θ = 3.7–26.0°
c = 11.591 (5) Å	µ = 0.09 mm⁻¹
β = 100.059 (5)°	T = 296 K
V = 1720.2 (14) Å³	Needle, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	3381 independent reflections
Radiation source: sealed tube	2169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
phi and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −22→13
T_min = 0.281, T_max = 0.397	k = −10→10
12516 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0428P)² + 0.2309P] where P = (F_o² + 2F_c²)/3
3381 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.19 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
O1	0.92494 (7)	0.95556 (14)	0.84820 (10)	0.0173 (3)
H1	0.911689	1.038088	0.879019	0.026*
O2	0.92659 (7)	0.63827 (16)	1.12657 (10)	0.0192 (3)
H2	0.917704	0.591870	1.185268	0.029*
O3	0.36888 (7)	0.68602 (17)	0.45972 (11)	0.0273 (4)
N1	1.11161 (8)	0.82930 (19)	0.98278 (13)	0.0185 (4)
N2	0.68013 (9)	0.68483 (19)	0.77772 (13)	0.0211 (4)
N3	0.62436 (9)	0.6015 (2)	0.78765 (13)	0.0215 (4)
C5	1.06621 (10)	0.7859 (2)	0.88320 (16)	0.0165 (4)
C4	1.08607 (10)	0.8094 (2)	0.77434 (16)	0.0180 (4)
H4	1.053929	0.778909	0.706776	0.022*
C1	1.17713 (11)	0.8933 (2)	0.97259 (17)	0.0208 (5)
H1A	1.209217	0.920515	1.041003	0.025*
C2	1.20001 (11)	0.9212 (2)	0.86736 (17)	0.0220 (5)
H2A	1.245666	0.967932	0.864834	0.026*
C3	1.15317 (10)	0.8778 (2)	0.76592 (16)	0.0205 (5)
H3	1.166638	0.894338	0.693146	0.025*
C6	0.99387 (10)	0.7089 (2)	0.89526 (16)	0.0184 (4)
H6A	1.003179	0.620943	0.952107	0.022*
H6B	0.972356	0.660762	0.820624	0.022*
C7	0.93790 (10)	0.8263 (2)	0.93306 (15)	0.0155 (4)
H7	0.958956	0.873197	1.009369	0.019*
C8	0.86746 (10)	0.7372 (2)	0.94404 (15)	0.0150 (4)
C9	0.80465 (10)	0.7454 (2)	0.85966 (16)	0.0171 (4)
H9	0.805051	0.809928	0.793644	0.021*
C10	0.74100 (10)	0.6607 (2)	0.87024 (15)	0.0167 (4)
C11	0.74037 (10)	0.5601 (2)	0.96750 (16)	0.0200 (5)
H11	0.698601	0.499720	0.974301	0.024*
C12	0.80215 (10)	0.5512 (2)	1.05329 (15)	0.0176 (4)
H12	0.801859	0.485124	1.118536	0.021*
C13	0.86500 (10)	0.6403 (2)	1.04309 (15)	0.0155 (4)
C14	0.56281 (10)	0.6283 (2)	0.69611 (16)	0.0199 (5)
C15	0.56281 (10)	0.7290 (2)	0.59953 (16)	0.0208 (5)
H15	0.605862	0.782243	0.589646	0.025*
C16	0.49943 (11)	0.7506 (2)	0.51820 (17)	0.0216 (5)
H16	0.499724	0.818338	0.453772	0.026*
C17	0.43502 (10)	0.6707 (2)	0.53292 (16)	0.0213 (5)
C18	0.43565 (11)	0.5659 (2)	0.62726 (16)	0.0235 (5)
H18	0.393131	0.509452	0.635834	0.028*
C19	0.49901 (10)	0.5451 (2)	0.70808 (16)	0.0228 (5)
H19	0.499085	0.474861	0.771220	0.027*
C20	0.36725 (11)	0.7824 (3)	0.35657 (17)	0.0298 (5)
H20A	0.318289	0.782488	0.311822	0.045*
H20B	0.400634	0.736834	0.310239	0.045*
H20C	0.381746	0.892552	0.378279	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0236 (8)	0.0129 (7)	0.0162 (7)	0.0019 (6)	0.0053 (6)	0.0002 (6)
O2	0.0192 (7)	0.0238 (8)	0.0139 (7)	−0.0022 (6)	0.0009 (6)	0.0042 (6)
O3	0.0176 (8)	0.0376 (9)	0.0252 (8)	−0.0018 (7)	−0.0007 (6)	0.0062 (7)
N1	0.0175 (9)	0.0192 (9)	0.0187 (9)	0.0023 (7)	0.0028 (7)	−0.0024 (7)
N2	0.0180 (9)	0.0235 (9)	0.0221 (9)	−0.0016 (8)	0.0044 (7)	−0.0040 (8)
N3	0.0183 (9)	0.0222 (9)	0.0239 (9)	−0.0016 (8)	0.0029 (8)	−0.0038 (7)
C5	0.0169 (11)	0.0125 (9)	0.0197 (10)	0.0038 (8)	0.0019 (9)	−0.0002 (8)
C4	0.0185 (11)	0.0169 (10)	0.0180 (10)	0.0020 (9)	0.0011 (8)	−0.0029 (8)
C1	0.0178 (11)	0.0213 (11)	0.0214 (11)	0.0014 (9)	−0.0020 (9)	−0.0053 (9)
C2	0.0155 (11)	0.0189 (10)	0.0326 (12)	−0.0017 (9)	0.0068 (10)	−0.0011 (9)
C3	0.0215 (11)	0.0195 (10)	0.0222 (11)	0.0026 (9)	0.0082 (9)	0.0030 (9)
C6	0.0207 (11)	0.0163 (10)	0.0185 (10)	0.0018 (9)	0.0043 (9)	0.0020 (8)
C7	0.0168 (10)	0.0168 (10)	0.0125 (9)	0.0002 (8)	0.0014 (8)	0.0024 (8)
C8	0.0167 (11)	0.0124 (10)	0.0158 (10)	0.0005 (8)	0.0028 (9)	−0.0029 (8)
C9	0.0189 (11)	0.0182 (10)	0.0150 (10)	0.0018 (9)	0.0052 (8)	−0.0007 (8)
C10	0.0160 (11)	0.0180 (10)	0.0153 (10)	0.0032 (9)	0.0007 (8)	−0.0034 (8)
C11	0.0160 (11)	0.0209 (11)	0.0241 (11)	−0.0042 (9)	0.0063 (9)	−0.0019 (9)
C12	0.0217 (11)	0.0175 (10)	0.0150 (10)	−0.0001 (9)	0.0067 (9)	0.0010 (8)
C13	0.0160 (11)	0.0150 (10)	0.0156 (10)	0.0036 (9)	0.0029 (9)	−0.0027 (8)
C14	0.0187 (11)	0.0205 (10)	0.0201 (11)	0.0035 (9)	0.0019 (9)	−0.0054 (9)
C15	0.0166 (11)	0.0206 (10)	0.0263 (11)	−0.0020 (9)	0.0066 (9)	−0.0045 (9)
C16	0.0212 (11)	0.0245 (12)	0.0191 (11)	0.0009 (9)	0.0032 (9)	−0.0011 (9)
C17	0.0168 (11)	0.0268 (12)	0.0192 (11)	0.0002 (9)	0.0001 (9)	−0.0068 (9)
C18	0.0185 (11)	0.0281 (11)	0.0245 (11)	−0.0049 (9)	0.0052 (9)	−0.0018 (9)
C19	0.0229 (12)	0.0246 (11)	0.0215 (11)	−0.0004 (10)	0.0059 (9)	0.0015 (9)
C20	0.0236 (12)	0.0348 (13)	0.0286 (12)	−0.0001 (10)	−0.0021 (10)	0.0049 (10)

Geometric parameters (Å, º) top

O1—C7	1.435 (2)	C7—H7	0.9800
O1—H1	0.8200	C8—C9	1.381 (2)
O2—C13	1.358 (2)	C8—C13	1.401 (2)
O2—H2	0.8200	C9—C10	1.387 (3)
O3—C17	1.365 (2)	C9—H9	0.9300
O3—C20	1.427 (2)	C10—C11	1.396 (3)
N1—C1	1.341 (2)	C11—C12	1.378 (2)
N1—C5	1.350 (2)	C11—H11	0.9300
N2—N3	1.256 (2)	C12—C13	1.392 (3)
N2—C10	1.425 (2)	C12—H12	0.9300
N3—C14	1.429 (2)	C14—C19	1.387 (3)
C5—C4	1.387 (3)	C14—C15	1.389 (3)
C5—C6	1.504 (3)	C15—C16	1.379 (3)
C4—C3	1.377 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.392 (3)
C1—C2	1.378 (3)	C16—H16	0.9300
C1—H1A	0.9300	C17—C18	1.388 (3)
C2—C3	1.378 (3)	C18—C19	1.375 (3)
C2—H2A	0.9300	C18—H18	0.9300
C3—H3	0.9300	C19—H19	0.9300
C6—C7	1.528 (3)	C20—H20A	0.9600
C6—H6A	0.9700	C20—H20B	0.9600
C6—H6B	0.9700	C20—H20C	0.9600
C7—C8	1.514 (2)

C7—O1—H1	109.5	C10—C9—H9	119.0
C13—O2—H2	109.5	C9—C10—C11	119.44 (17)
C17—O3—C20	117.19 (15)	C9—C10—N2	115.63 (17)
C1—N1—C5	117.47 (16)	C11—C10—N2	124.93 (17)
N3—N2—C10	114.01 (16)	C12—C11—C10	119.43 (17)
N2—N3—C14	113.99 (16)	C12—C11—H11	120.3
N1—C5—C4	121.23 (17)	C10—C11—H11	120.3
N1—C5—C6	117.29 (16)	C11—C12—C13	120.52 (17)
C4—C5—C6	121.47 (17)	C11—C12—H12	119.7
C3—C4—C5	120.27 (18)	C13—C12—H12	119.7
C3—C4—H4	119.9	O2—C13—C12	122.62 (16)
C5—C4—H4	119.9	O2—C13—C8	116.61 (16)
N1—C1—C2	124.26 (18)	C12—C13—C8	120.77 (16)
N1—C1—H1A	117.9	C19—C14—C15	119.35 (17)
C2—C1—H1A	117.9	C19—C14—N3	115.39 (17)
C1—C2—C3	117.98 (18)	C15—C14—N3	125.25 (18)
C1—C2—H2A	121.0	C16—C15—C14	120.48 (18)
C3—C2—H2A	121.0	C16—C15—H15	119.8
C4—C3—C2	118.78 (18)	C14—C15—H15	119.8
C4—C3—H3	120.6	C15—C16—C17	119.75 (18)
C2—C3—H3	120.6	C15—C16—H16	120.1
C5—C6—C7	114.81 (16)	C17—C16—H16	120.1
C5—C6—H6A	108.6	O3—C17—C18	115.46 (18)
C7—C6—H6A	108.6	O3—C17—C16	124.79 (18)
C5—C6—H6B	108.6	C18—C17—C16	119.75 (18)
C7—C6—H6B	108.6	C19—C18—C17	120.14 (19)
H6A—C6—H6B	107.5	C19—C18—H18	119.9
O1—C7—C8	111.64 (15)	C17—C18—H18	119.9
O1—C7—C6	107.77 (14)	C18—C19—C14	120.47 (18)
C8—C7—C6	110.83 (15)	C18—C19—H19	119.8
O1—C7—H7	108.8	C14—C19—H19	119.8
C8—C7—H7	108.8	O3—C20—H20A	109.5
C6—C7—H7	108.8	O3—C20—H20B	109.5
C9—C8—C13	117.68 (17)	H20A—C20—H20B	109.5
C9—C8—C7	122.90 (16)	O3—C20—H20C	109.5
C13—C8—C7	119.42 (16)	H20A—C20—H20C	109.5
C8—C9—C10	122.10 (17)	H20B—C20—H20C	109.5
C8—C9—H9	118.9

C10—N2—N3—C14	178.77 (15)	C9—C10—C11—C12	2.2 (3)
C1—N1—C5—C4	−1.1 (3)	N2—C10—C11—C12	−177.81 (17)
C1—N1—C5—C6	177.95 (16)	C10—C11—C12—C13	−0.5 (3)
N1—C5—C4—C3	0.1 (3)	C11—C12—C13—O2	178.50 (16)
C6—C5—C4—C3	−178.93 (17)	C11—C12—C13—C8	−1.8 (3)
C5—N1—C1—C2	1.8 (3)	C9—C8—C13—O2	−177.94 (15)
N1—C1—C2—C3	−1.3 (3)	C7—C8—C13—O2	2.6 (2)
C5—C4—C3—C2	0.3 (3)	C9—C8—C13—C12	2.3 (3)
C1—C2—C3—C4	0.2 (3)	C7—C8—C13—C12	−177.13 (16)
N1—C5—C6—C7	71.7 (2)	N2—N3—C14—C19	−176.48 (16)
C4—C5—C6—C7	−109.2 (2)	N2—N3—C14—C15	3.4 (3)
C5—C6—C7—O1	58.2 (2)	C19—C14—C15—C16	2.2 (3)
C5—C6—C7—C8	−179.36 (15)	N3—C14—C15—C16	−177.72 (18)
O1—C7—C8—C9	18.4 (2)	C14—C15—C16—C17	−0.1 (3)
C6—C7—C8—C9	−101.8 (2)	C20—O3—C17—C18	−175.10 (17)
O1—C7—C8—C13	−162.15 (15)	C20—O3—C17—C16	4.5 (3)
C6—C7—C8—C13	77.7 (2)	C15—C16—C17—O3	178.39 (17)
C13—C8—C9—C10	−0.6 (3)	C15—C16—C17—C18	−2.1 (3)
C7—C8—C9—C10	178.84 (17)	O3—C17—C18—C19	−178.22 (17)
C8—C9—C10—C11	−1.7 (3)	C16—C17—C18—C19	2.2 (3)
C8—C9—C10—N2	178.37 (16)	C17—C18—C19—C14	−0.1 (3)
N3—N2—C10—C9	177.37 (16)	C15—C14—C19—C18	−2.0 (3)
N3—N2—C10—C11	−2.6 (3)	N3—C14—C19—C18	177.85 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of rings C8–C13 and C14–C19, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.04	2.801 (2)	154
O2—H2···O1ⁱⁱ	0.82	1.91	2.686 (2)	158
C4—H4···O2ⁱⁱⁱ	0.93	2.47	3.165 (2)	132
C3—H3···Cg2^iv	0.93	2.82	3.593 (3)	141
C19—H19···Cg3^v	0.93	2.98	3.841 (3)	155

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+2, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Crystal structure and Hirshfeld surface analysis of (E)-2-[1-hy­droxy-2-(pyridin-2-yl)eth­yl]-4-[2-(4-meth­oxy­phen­yl)diazen-1-yl]phenol

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure and Hirshfeld surface analysis of (E)-2-[1-hydroxy-2-(pyridin-2-yl)ethyl]-4-[2-(4-methoxyphenyl)diazen-1-yl]phenol