Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-meth­oxy­phen­yl)picolinamide

Burieva, D.; Torambetov, B.; Bobonazarova, S.; Abdushukurov, A.; Kholikov, T.; Khan, A.A.; Ashurov, J.; Yusufov, M.

doi:10.1107/S2056989024010843

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Volume 80| Part 12| December 2024|

https://doi.org/10.1107/S2056989024010843

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Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-methoxyphenyl)picolinamide

Dilnoza Burieva,^a Batirbay Torambetov,^a,^b ^* Sarvinoz Bobonazarova,^a Anvar Abdushukurov,^a Tursinali Kholikov,^a Akram A Khan,^b Jamshid Ashurov ^c and Mukhriddin Yusufov ^a

^aNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St., Tashkent, 100174, Uzbekistan, ^bPhysical and Material Chemistry Division, CSIR-National Chemical Laboratory, Pune 411008, India, and ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek, St, 83, Tashkent, 100125, Uzbekistan
^*Correspondence e-mail: torambetov_b@mail.ru

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 23 October 2024; accepted 8 November 2024; online 14 November 2024)

The synthesis, crystal structure, and Hirshfeld surface analysis of N-(4-methoxyphenyl)picolinamide (MPPA), C₁₃H₁₂N₂O₂, are presented. MPPA crystallizes in the monoclinic space group P2₁/n, with a single molecule in the asymmetric unit. Structural analysis reveals that all non-hydrogen atoms are nearly coplanar, and the molecule exhibits two intramolecular hydrogen bonds that stabilize its conformation. Supramolecular features include significant intermolecular interactions, primarily C—H⋯π and various hydrogen bonds, contributing to the overall crystal cohesion, as confirmed by energy framework calculations yielding a total interaction energy of −138.3 kJ mol⁻¹. Hirshfeld surface analysis indicates that H⋯H interactions dominate, followed by C⋯H and O⋯H interactions, highlighting the role of van der Waals forces and hydrogen bonding in crystal packing.

Keywords: crystal structure; molecular structure; picolinic acid; picolinamide; Hirshfeld surface analysis.

CCDC reference: 2401430

1. Chemical context

The synthesis of amide derivatives of carbonic acid is a vital area of organic chemistry, owing to the widespread presence and significance of amide bonds in various applications. These bonds are fundamental components in polymers such as nylon, proteins, and peptides, as well as in natural products such as paclitaxel and penicillin (Valeur & Bradley, 2009 ). Notably, approximately 25% of pharmaceuticals contain at least one amide bond, highlighting their importance in drug development (Ghose et al., 1999 ; Kamanna et al., 2020 ; Goodreid et al., 2014 ).

Amide-linked compounds are typically synthesized through acylation methods, often involving acyl chlorides or coupling agents that facilitate the reaction between carboxylic acids and amines (Montalbetti & Falque, 2005 ; Pon et al., 1999 ; Han & Kim, 2004 ; Valeur & Bradley, 2009). Moreover, the use of orthoboric acid and organoboronic compounds has gained prominence for direct amide synthesis, demonstrating their effectiveness as catalysts in these reactions (Tang, 2005 ).

Among the diverse array of organic substances, heterocyclic compounds are particularly significant, especially heterocyclic aromatic compounds, which play crucial roles in biological systems. Pyridine and its derivatives are key representatives of this class (Kaiser et al., 1996 ). Specifically, 2-pyridinecarboxylic acid amides are noteworthy for their versatility as reagents and catalysts in various organic syntheses. Their strong ligand properties in coordination chemistry have also been extensively studied (Sambiagio et al., 2016 ).

The combination of a pyridine fragment with an amide bond not only enhances the reactivity of these compounds but also expands their applicability across multiple sectors of the chemical industry. The nitrogen atom in the pyridine ring possesses an unshared electron pair, which, along with the electron-rich carbonyl group of the amide, facilitates the formation of coordination bonds with various metals (Mishra et al., 2008 ; Almodares et al., 2014 ; Wang et al., 2019 ; Basri et al., 2017 ). This interaction paves the way for the development of complex compounds with tailored properties, making these derivatives integral to advancements in both synthetic and applied chemistry.

2. Structural commentary

N-(4-Methoxyphenyl)picolinamide (MPPA) crystallizes in the primitive centrosymmetric monoclinic space group P2₁/n. The asymmetric unit consists of a single molecule of MPPA (Fig. 1). All atoms, except for the hydrogen atoms, lie nearly in a plane, with a maximum deviation of 0.195 Å for atom C11. The dihedral angle between the mean planes of the pyridine ring (C1–C5/N1) and the benzene ring (C7–C12) is 14.25 (5)°. The torsion angles for the groups N1—C5—C6—N2 and C6—N2—C7—C8 are 3.1 (4)° and 12.7 (6)°, respectively. The distance between C6 and O1 in the amide moiety is 1.233 (4) Å (Shen et al., 2019 ; Razzoqova et al., 2022 ). The conformation of the methoxy group is nearly planar with respect to the benzene ring, with a C9—C10—O2—C13 torsion angle of 7.5 (5)°. The nitrogen atom (N2) in the imino group is also planar, with the sum of the bond angles around it being equal to 360°. There are two intramolecular hydrogen bonds: one between the pyridine nitrogen (N1) and the amide nitrogen (N2) (N2—H2⋯N1 = 2.18 Å), and another between the amide oxygen (O1) and the benzene carbon (C8) (C8—H8⋯O1 = 2.37 Å). These interactions form S(5) and S(6) ring motifs, respectively (Bernstein et al., 1995 ), which contribute to the stabilization of the molecular conformation (Fig. 1, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1	0.86	2.18	2.635 (4)	113
C1—H1⋯O1ⁱ	0.93	2.58	3.500 (4)	173
C3—H3⋯N1ⁱⁱ	0.93	2.74	3.402 (4)	129
C8—H8⋯O1	0.93	2.37	2.947 (4)	120
C11—H11⋯O2ⁱⁱⁱ	0.93	2.63	3.558 (4)	173
C13—H13C⋯O1^iv	0.96	2.51	3.468 (4)	173
C13—H13B⋯Cg1^v	0.96	2.71	3.500 (4)	140
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) ; (iv) ; (v) .

Figure 1
A view of the molecular structure of MPPA, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines.

3. Supramolecular features and energy framework calculations

In the crystal structure, molecules are interconnected through weak interactions. Notably, an intermolecular C—H⋯π interaction (C13—H13B⋯Cg1) involves the centroid of the C7–C12 benzene ring (see Table 1, Fig. 2). These interactions are crucial for the packing of molecules along the a-axis direction. Additionally, several weak hydrogen bonds further contribute to the structural integrity. These include C1—H1⋯O1, C3—H3⋯N1, C11—H11⋯O2 and C13—H13⋯O1 and help consolidate the molecules along the b- and c-axis directions (see Table 1, Fig. 3). Notably, the C11—H11⋯O2 interaction results in the formation of inversion dimers, creating closed eight-membered rings characterized by an R₂²(8) graph-set motif (Etter, 1990 ).

Figure 2
Crystal packing of MPPA along the [100] direction. C—H⋯Cg interactions are shown as cyan dashed lines.

Figure 3
Crystal packing of MPPA in a projection along the [100] direction. Hydrogen bonds are shown as cyan lines. The colour codes of the atoms participating in interactions and corresponding symmetry operations of neighbours are similar.

To identify the intermolecular interactions of MPPA, energy framework calculations were carried out using CrystalExplorer (Spackman et al., 2021 ). The wavefunctions were derived from the SCXRD CIF file using the Gaussian B3LYP-D2/6-31G(d,p) method. The total interaction energy (E_tot) was calculated by combining the electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and repulsion (E_rep) contributions, giving a value of −138.3 kJ mol⁻¹. Electrostatic and dispersion forces are the dominant contributors to the stability of the crystal, particularly along the a-axis direction (Fig. 4). Interaction energies were computed for molecules within a 3.8 Å radius of a reference molecule, omitting those below 5 kJ mol⁻¹ for clarity. In the energy framework visualization, thick cylinders represented stronger interactions, allowing easy identification of significant intermolecular interactions (Fig. 4).

Figure 4
Energy framework calculations of the MPPA crystal are observed along the a, b and c axes.

4. Hirshfeld surface analysis

The studies carried out on the Hirshfeld surface show that H⋯H interactions are the most abundant at 47% of the total intermolecular interactions, suggesting the importance of van der Waals interactions in the structural organization of the crystal due to the hydrogen atoms. The C⋯H interactions come second, accounting for 22% and signify the presence of weak dispersive forces or possible C—H⋯π interactions, which further help stabilize the crystal. The 15.4% contribution of O⋯H interactions indicate the presence of strong hydrogen-bonding interactions between oxygen atoms and hydrogen atoms, which play a key role in the crystal packing. The smallest contributions to the crystal packing are from N⋯H (5%), C⋯C (4.8%), C⋯N (3.4%) and C⋯O (1.9%) contacts (Fig. 5).

Figure 5
View of the three-dimensional Hirshfeld surfaces plotted over d_norm and contributions of the various contacts to the two-dimensional fingerprint plots of the MPPA molecule.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.45, last updated March 2024; Groom et al., 2016 ) did not find any structures for the synthesized MPPA. However, two complex compounds were identified in which MPPA acts as a bidentate ligand, coordinating with Co and Rh metals (BAKQIR, Ghandhi et al., 2021 ; BEDSAG, Bhattacharya et al., 2012 ). The authors also reported structures of various picolinamides, including several benzene derivatives. Among these, mono-substituted derivatives such as o-, m-, and p-monochloro (KEHWED, KEHWAZ, GEPQIC; Gallagher et al., 2022 ;), p-fluoro (KAHRUI; Wilson & Munro 2010 ), p-bromo (WUVYIV; Qi et al., 2003 ) , p-hydroxy (LUGPOV; Ali et al., 2014 ), p-nitro (KAHSAP; Wilson et al., 2010), and o-, m-, and p-methyl (UXEYOM, UXEYIG, UXEYEC; Mocilac & Gallagher, 2011 ) picolinamides were documented. In these molecules, the mean planes of the pyridine and benzene rings are generally nearly coplanar, with slight twisting in some cases. Notably, the p-fluoro and p-methyl derivatives exhibit significant twisting, with dihedral angles of 36.26 and 33.63°, respectively.

6. Synthesis and crystallization

A mixture of 0.615 g (0.005 mol) of picolinic acid, 1.23 g (0.01 mol) of p-anisidine, and 0.31 g (0.005 mol) of orthoboric acid was thoroughly combined and placed in a reaction flask. The flask was then subjected to microwave irradiation for 40 minutes. Upon completion of the reaction, a 10% NaHCO₃ solution was added to the mixture, and the resulting solid was filtered off. The filtrate was recrystallized using a 30% ethanol–water solution, yielding 0.798 g (70%) of the final product, m.p. 362–363 K.

¹H NMR (600 MHz, CDCl₃) (J, Hz): δ 9.92 (s, 1H), 8.60 (ddt, J = 4.8, 1.7, 0.8 Hz, 1H), 8.29 (dt, J = 7.8, 1.1 Hz, 1H), 7.92–7.86 (m, 1H), 7.73–7.67 (m, 2H), 7.49–7.44 (m, 1H), 6.95–6.90 (m, 2H), 3.81 (s, 3H). ¹³C NMR (151 MHz, CDCl₃): δ 161.86, 156.52, 150.11, 148.07, 137.77, 131.16, 126.43, 122.44, 121.37, 114.38, 55.62. m/z (MS): [M]⁺ 228.00.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All the hydrogen atoms were located in difference-Fourier maps and reﬁned using an isotropic approximation.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₂
M_r	228.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.0082 (9), 20.728 (4), 11.1549 (14)
β (°)	96.998 (15)
V (Å³)	1149.3 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.74
Crystal size (mm)	0.10 × 0.08 × 0.07

Data collection
Diffractometer	Xcalibur, Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.669, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7362, 2166, 975
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.139, 1.00
No. of reflections	2166
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2401430

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024010843/dx2062sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024010843/dx2062Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024010843/dx2062Isup3.cml

checkCIF report

Computing details top

N-(4-Methoxyphenyl)pyridine-2-carboxamide top

Crystal data top

C₁₃H₁₂N₂O₂	F(000) = 480
M_r = 228.25	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 5.0082 (9) Å	Cell parameters from 638 reflections
b = 20.728 (4) Å	θ = 4.3–50.5°
c = 11.1549 (14) Å	µ = 0.74 mm⁻¹
β = 96.998 (15)°	T = 293 K
V = 1149.3 (3) Å³	Block, colourless
Z = 4	0.10 × 0.08 × 0.07 mm

Data collection top

Xcalibur, Ruby diffractometer	2166 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	975 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
Detector resolution: 10.2576 pixels mm^-1	θ_max = 70.0°, θ_min = 4.5°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	k = −23→25
T_min = 0.669, T_max = 1.000	l = −13→9
7362 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.061	w = 1/[σ²(F_o²) + (0.0373P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.139	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.15 e Å⁻³
2166 reflections	Δρ_min = −0.16 e Å⁻³
156 parameters	Extinction correction: SHELXL2016/6 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0017 (4)
Primary atom site location: dual

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	0.7804 (5)	0.64248 (12)	0.5355 (2)	0.0708 (8)
O2	−0.0904 (5)	0.46914 (13)	0.1774 (2)	0.0732 (8)
N2	0.6732 (5)	0.65548 (14)	0.3324 (2)	0.0598 (8)
H2	0.709512	0.679337	0.273443	0.072*
N1	1.0276 (6)	0.74910 (15)	0.3271 (2)	0.0601 (8)
C10	0.0926 (7)	0.51451 (18)	0.2243 (3)	0.0586 (10)
C6	0.8116 (7)	0.66959 (18)	0.4398 (3)	0.0578 (10)
C7	0.4767 (6)	0.60741 (18)	0.3013 (3)	0.0551 (10)
C5	1.0171 (7)	0.72159 (18)	0.4350 (3)	0.0527 (9)
C4	1.1852 (7)	0.73839 (18)	0.5373 (3)	0.0595 (10)
H4	1.171623	0.718024	0.610576	0.071*
C9	0.1619 (7)	0.52633 (19)	0.3453 (3)	0.0648 (11)
H9	0.079459	0.503135	0.401950	0.078*
C1	1.2108 (7)	0.79571 (19)	0.3221 (3)	0.0677 (11)
H1	1.220637	0.815677	0.248061	0.081*
C3	1.3734 (7)	0.78589 (19)	0.5287 (3)	0.0661 (11)
H3	1.491329	0.797526	0.596193	0.079*
C8	0.3529 (7)	0.5724 (2)	0.3835 (3)	0.0656 (11)
H8	0.398288	0.579727	0.465682	0.079*
C12	0.4052 (7)	0.59542 (19)	0.1794 (3)	0.0690 (11)
H12	0.486200	0.618804	0.122515	0.083*
C2	1.3864 (7)	0.81602 (19)	0.4202 (3)	0.0688 (11)
H2A	1.509095	0.849017	0.412757	0.083*
C11	0.2162 (7)	0.5494 (2)	0.1416 (3)	0.0730 (12)
H11	0.171226	0.541804	0.059426	0.088*
C13	−0.2421 (7)	0.43698 (19)	0.2588 (3)	0.0778 (12)
H13A	−0.372539	0.409360	0.214373	0.117*
H13B	−0.332549	0.468255	0.302912	0.117*
H13C	−0.123774	0.411569	0.314264	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0822 (19)	0.079 (2)	0.0492 (14)	−0.0123 (15)	0.0019 (13)	0.0042 (13)
O2	0.0762 (18)	0.077 (2)	0.0654 (16)	−0.0158 (16)	0.0045 (14)	−0.0085 (14)
N2	0.071 (2)	0.066 (2)	0.0402 (15)	−0.0061 (17)	−0.0033 (15)	0.0030 (14)
N1	0.068 (2)	0.065 (2)	0.0453 (17)	0.0046 (18)	0.0012 (14)	0.0028 (15)
C10	0.055 (2)	0.063 (3)	0.056 (2)	−0.002 (2)	0.0000 (18)	−0.0060 (19)
C6	0.064 (2)	0.060 (3)	0.049 (2)	0.007 (2)	0.0013 (18)	−0.0038 (18)
C7	0.056 (2)	0.057 (3)	0.050 (2)	0.004 (2)	−0.0028 (18)	−0.0055 (18)
C5	0.057 (2)	0.055 (3)	0.0440 (19)	0.0066 (19)	0.0002 (17)	−0.0019 (17)
C4	0.064 (2)	0.069 (3)	0.0440 (19)	0.000 (2)	0.0012 (18)	0.0016 (18)
C9	0.064 (2)	0.077 (3)	0.055 (2)	−0.008 (2)	0.0143 (19)	−0.003 (2)
C1	0.075 (3)	0.072 (3)	0.057 (2)	0.006 (2)	0.012 (2)	0.011 (2)
C3	0.066 (2)	0.078 (3)	0.051 (2)	−0.008 (2)	−0.0039 (19)	−0.006 (2)
C8	0.068 (3)	0.083 (3)	0.046 (2)	−0.002 (2)	0.0065 (19)	−0.007 (2)
C12	0.082 (3)	0.072 (3)	0.051 (2)	−0.014 (2)	−0.004 (2)	0.0076 (19)
C2	0.074 (3)	0.071 (3)	0.062 (2)	−0.012 (2)	0.010 (2)	−0.005 (2)
C11	0.085 (3)	0.083 (3)	0.047 (2)	−0.014 (2)	−0.008 (2)	0.003 (2)
C13	0.064 (3)	0.078 (3)	0.092 (3)	−0.009 (2)	0.013 (2)	−0.001 (2)

Geometric parameters (Å, º) top

O1—C6	1.233 (4)	C4—C3	1.374 (5)
O2—C10	1.371 (4)	C9—H9	0.9300
O2—C13	1.419 (4)	C9—C8	1.381 (5)
N2—H2	0.8600	C1—H1	0.9300
N2—C6	1.341 (4)	C1—C2	1.384 (4)
N2—C7	1.413 (4)	C3—H3	0.9300
N1—C5	1.339 (4)	C3—C2	1.371 (4)
N1—C1	1.338 (4)	C8—H8	0.9300
C10—C9	1.374 (4)	C12—H12	0.9300
C10—C11	1.378 (5)	C12—C11	1.373 (5)
C6—C5	1.496 (5)	C2—H2A	0.9300
C7—C8	1.376 (5)	C11—H11	0.9300
C7—C12	1.386 (4)	C13—H13A	0.9600
C5—C4	1.378 (4)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600

C10—O2—C13	117.6 (3)	N1—C1—C2	124.0 (3)
C6—N2—H2	115.0	C2—C1—H1	118.0
C6—N2—C7	129.9 (3)	C4—C3—H3	120.2
C7—N2—H2	115.0	C2—C3—C4	119.6 (3)
C1—N1—C5	116.6 (3)	C2—C3—H3	120.2
O2—C10—C9	125.0 (3)	C7—C8—C9	120.7 (3)
O2—C10—C11	116.0 (3)	C7—C8—H8	119.6
C9—C10—C11	118.9 (3)	C9—C8—H8	119.6
O1—C6—N2	124.6 (4)	C7—C12—H12	119.6
O1—C6—C5	121.3 (3)	C11—C12—C7	120.8 (4)
N2—C6—C5	114.1 (3)	C11—C12—H12	119.6
C8—C7—N2	124.4 (3)	C1—C2—H2A	121.1
C8—C7—C12	118.4 (3)	C3—C2—C1	117.8 (4)
C12—C7—N2	117.2 (3)	C3—C2—H2A	121.1
N1—C5—C6	116.2 (3)	C10—C11—H11	119.7
N1—C5—C4	123.4 (3)	C12—C11—C10	120.5 (3)
C4—C5—C6	120.4 (3)	C12—C11—H11	119.7
C5—C4—H4	120.7	O2—C13—H13A	109.5
C3—C4—C5	118.6 (3)	O2—C13—H13B	109.5
C3—C4—H4	120.7	O2—C13—H13C	109.5
C10—C9—H9	119.7	H13A—C13—H13B	109.5
C10—C9—C8	120.6 (3)	H13A—C13—H13C	109.5
C8—C9—H9	119.7	H13B—C13—H13C	109.5
N1—C1—H1	118.0

O1—C6—C5—N1	−177.9 (3)	C7—N2—C6—O1	−2.8 (6)
O1—C6—C5—C4	2.9 (5)	C7—N2—C6—C5	176.1 (3)
O2—C10—C9—C8	178.7 (3)	C7—C12—C11—C10	0.4 (6)
O2—C10—C11—C12	−179.1 (3)	C5—N1—C1—C2	0.4 (5)
N2—C6—C5—N1	3.1 (4)	C5—C4—C3—C2	1.2 (5)
N2—C6—C5—C4	−176.1 (3)	C4—C3—C2—C1	−1.6 (6)
N2—C7—C8—C9	179.8 (3)	C9—C10—C11—C12	−0.1 (6)
N2—C7—C12—C11	179.9 (3)	C1—N1—C5—C6	179.9 (3)
N1—C5—C4—C3	0.1 (5)	C1—N1—C5—C4	−0.9 (5)
N1—C1—C2—C3	0.8 (6)	C8—C7—C12—C11	−0.3 (6)
C10—C9—C8—C7	0.2 (6)	C12—C7—C8—C9	0.0 (6)
C6—N2—C7—C8	12.7 (6)	C11—C10—C9—C8	−0.2 (6)
C6—N2—C7—C12	−167.5 (3)	C13—O2—C10—C9	7.5 (5)
C6—C5—C4—C3	179.2 (3)	C13—O2—C10—C11	−173.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.86	2.18	2.635 (4)	113
C1—H1···O1ⁱ	0.93	2.58	3.500 (4)	173
C3—H3···N1ⁱⁱ	0.93	2.74	3.402 (4)	129
C8—H8···O1	0.93	2.37	2.947 (4)	120
C11—H11···O2ⁱⁱⁱ	0.93	2.63	3.558 (4)	173
C13—H13C···O1^iv	0.96	2.51	3.468 (4)	173
C13—H13B···Cg1^v	0.96	2.71	3.500 (4)	140

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

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-meth­­oxy­phen­yl)picolinamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features and energy framework calculations

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

References

research communications

Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-methoxyphenyl)picolinamide

3. Supramolecular features and energy framework calculations