Mol­ecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitro­benzo­yloxy)aceto­phenone isomers

Bogdanov, G.; Bustos, J.; Glebov, V.; Oskolkov, E.; Tillotson, J.P.; Timofeeva, T.V.

doi:10.1107/S2056989020006295

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Volume 76| Part 6| June 2020| Pages 857-861

https://doi.org/10.1107/S2056989020006295

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Molecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitrobenzoyloxy)acetophenone isomers

Georgii Bogdanov,^a,^b ^* Jenna Bustos,^a Viktor Glebov,^a Evgenii Oskolkov,^a John P. Tillotson ^c and Tatiana V. Timofeeva ^a

^aDepartment of Chemistry, New Mexico Highlands University, Las Vegas, New Mexico, 87701, USA, ^bDepartment of Chemical and Biomolecular Engineering, University of California, Irvine, Irvine, California, 92617, USA, and ^cSchool of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA
^*Correspondence e-mail: bogdgv@gmail.com

Edited by G. Diaz de Delgado, Universidad de Los Andes, Venezuela (Received 18 February 2020; accepted 9 May 2020; online 19 May 2020)

The two isomers 2′-(4-nitrobenzoyloxy)acetophenone (systematic name: 2-acetylphenyl 4-nitrobenzoate) (I) and 2′-(2-nitrobenzoyloxy)acetophenone (systematic name: 2-acetylphenyl 2-nitrobenzoate) (II), both C₁₅H₁₁NO₅, with para and ortho positions of the nitro substituent have been crystallized and studied. It is evident that the variation in the position of the nitro group causes a significant difference in the molecular conformations: the dihedral angle between the aromatic fragments in the molecule of I is 84.80 (4)°, while that in the molecule of II is 6.12 (7)°. Diffraction analysis revealed the presence of a small amount of water in the crystal of I. DFT calculations of the molecular energy demonstrate that the ortho substituent causes a higher energy for isomer II, while crystal lattice energy calculations show that the values are almost equal for two isomers.

Keywords: 2′-(nitrobenzoyloxy)acetophenone isomers; crystal structure; molecular conformation; DFT calculations; lattice energy.

CCDC references: 2002786; 2002785

1. Chemical context

2′-Benzoyloxyacetophenones, also known as 2-acetylphenyl benzoates, with and without additional substituents are used in the synthesis of materials with different biomedical applications (Singh et al., 2017 ; Vyas et al., 2016 ; Ali et al., 2017 ). The two isomers presented here, 2′-(4-nitrobenzoyloxy)acetophenone (I) and 2′-(2-nitrobenzoyloxy)acetophenone (II), have been employed as starting materials for the Baker–Venkataraman rearrangement (Baker, 1933 ; Mahal & Venkataraman, 1934 ) to obtain 1,3-diketones, namely 1-(2-hydroxyphenyl)-3-(nitrophenyl)propan-1,3-diones, with different positions of the nitro substituents. These diketones have been used to synthesize substituted nitroflavones, which are potentially useful as pharmaceutical materials (Barros & Silva, 2006 ). Recently, halogen- and/or nitro-substituted phenyl benzoates were found to be plastic crystals. This characteristic is related to the presence of the flexible –C—CO– synthon in the molecules (Saha & Desiraju, 2017 ; Saha et al., 2018 ).

2. Structural commentary

The corresponding bond lengths and bond angles in isomers I and II are very similar in the two molecules and are close to the standard values. The only unexpected value is angle O1—C14—C7, which is 111.42 (10)° (I) and 111.15 (9)° (II) for steric reasons, which is quite common for a bridging geometry in molecules with the same molecular core, such as phenyl benzoate and fluorinated phenyl benzoates (Dey & Chopra, 2017 ).

In both isomers, the nitro groups lie in the plane of the corresponding phenyl ring [torsion angles C9—C10—N1—O4 = 0.32 (17)° and C7—C12—N1—O3 = 1.08 (14)°, in isomers I and II respectively], while the acetyl groups are slightly twisted from the phenyl planes [torsion angles C1—C6—C15—O5 = 8.35 (18)° and C1—C6—C15—O5 = 3.97 (16)°]. The conformations of the two molecules are quite different (Fig. 1). There are two short intramolecular contacts between the oxygen atoms of the carbonyls and the ether group [O1⋯O5 = 2.694 (1) Å] and the oxygens of two carbonyl groups [O2⋯O5 = 3.008 (2) Å) in molecule I; in molecule II there are two short contacts between ether oxygen and carbonyl groups [O1⋯O3 and O1⋯O5 = 2.885 (1) and 2.704 (1) Å, respectively].

Figure 1
Views of the formula units of (a) isomer I and (b) isomer II with the atom-labeling schemes. Displacement ellipsoids are shown with 50% probability. H atoms are shown as fixed spheres of radius 0.15 Å.

In the molecule of I, the dihedral angle between the phenyl rings is 84.84 (6)° (i.e. rings are almost perpendicular to each other), while in the molecule of II the phenyl rings are almost parallel, the dihedral angle between them being 6.11 (4)°. It is possible that the significant difference in the molecular conformations of the isomers is caused by the different positions of the nitro substituents.

3. DFT calculations

DFT calculations of isomers I and II at the B3LYP/6-311G(d,p) level of theory were carried out using GAUSSIAN 16 software (Frisch et al., 2016 ). The geometrical parameters of the two isomers were optimized starting from the molecular geometry in the crystal. No significant differences between the experimental and optimized bond lengths and angles were found. As mentioned above, the observed O1—C14—C7 angles are smaller than the standard value, and the calculated values are also smaller [111.41° (I) and 110.04° (II), which are very close to experimental values of 111.42 (10)° (I) and 111.15 (9)° (II)]. A comparison of the conformational characteristics of isomers I and II according to X-ray data and quantum chemical DFT calculations is presented in Table 1. This shows that the deviations of the nitro and acetyl groups from the planes of the corresponding aromatic rings are small and almost the same according to the X-ray and DFT data for isomer I. The data for isomer II indicate that the sterically stressed ortho position of the nitro group leads to larger differences between the molecular conformation in the crystal and that calculated for an isolated molecule. Hence, the deviations of the nitro and acetyl groups from the planes of aromatic rings are larger, as well as from the bridging plane, which is different in the isolated molecule of II.

Table 1
Comparison of conformational characteristics (°) of isomers I and II from diffraction (X-ray) and computational (DFT) data

Conformational parameters	Isomer I – X-ray	Isomer I – DFT	Isomer II – X-ray	Isomer II – DFT
C9—C10—N1—O4	0.32 (17)	0.14	–	–
C11—C12—N1—O4	–	–	−1.10 (15)	−21.06
C5—C6—C15—C13	7.54 (17)	6.03	−3.80 (15)	−10.18
C12—C7—C14—O1	167.74 (11)	172.87	−85.81 (12)	−65.72
C7—C14—O1—C1	−178.76 (10)	171.54	−178.19 (8)	−175.37
C6—C1—O1—C14	−77.59 (14)	−77.23	81.05 (12)	82.74
Ar/Ar	84.80 (4)	87.03	6.12 (7)	21.04

4. Supramolecular features

As a result of the presence in isomers I and II of oxygen atoms of the carbonyl, nitro, and ether groups, the title molecules are capable of forming C—H⋯O hydrogen bonds (Tables 2 and 3). In the crystal of I, a low-occupancy [0.074 (2)] partial water molecule forms a bridge between two molecules of I (Fig. 2). The O2⋯O6 distance of 2.912 (6) Å indicates that this interaction is weak (Brown, 1976 ). In addition, π–π interactions between phenyl rings are observed in both structures. In I, the π–π interactions lead to the formation of dimers (Fig. 3a), while in II they lead to the formation of ladder-like chains along the [1 16 $[\overline1]$ ] direction (Fig. 3b). The crystal packing is shown in Figs. 4 and 5. Despite the differences in the packing in the crystals of the two isomers, their lattice energies are very similar (see below).

Table 2
Hydrogen-bond geometry (Å, °) for I

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O2	0.94 (1)	1.98 (2)	2.912 (6)	173 (2)
C13—H13A⋯O2ⁱ	0.998 (19)	2.638 (19)	3.594 (2)	160.6 (14)
C11—H11⋯O5ⁱⁱ	0.960 (16)	2.600 (17)	3.4725 (17)	151.3 (12)
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Table 3
Hydrogen-bond geometry (Å, °) for II

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.941 (16)	2.646 (15)	3.2711 (19)	124.4 (12)
Symmetry code: (i) -x+2, -y, -z+2.

Figure 2
Structure of the dimeric associate in the crystal of I with the molecules connected by a 0.074 (2) occupancy bridging water molecule.

Figure 3
Molecular associates connected by π–π interactions in the crystals of I (dimer) and II (ladder-like chain). In the dimer (I), the distance between parallel phenyl rings is given. In the chain (II), several short contacts between carbon atoms are indicated.

Figure 4
Molecular packing in the crystal of isomer I. Molecules of water with 0.074 (2) occupancy are shown.

Figure 5
Molecular packing in the crystal of isomer II.

5. Lattice energy calculations

The crystal lattice energies (Table 4) were calculated using the atom–atom force field implemented in the CLP-PIXEL program package (version 3.0, available from https://www.angelogavezzotti.it; Gavezzotti, 2011 ). The hydrogen-atom positions for the lattice energy calculations were assigned by the software. In structure II, which has a higher packing coefficient, the repulsive and Coulombic components are larger than in the structure of I, which has a lower packing coefficient, although the dispersion energy is lower in I. The total contribution of all the components results in the lattice energy for the crystals of the two isomers being almost equal. As the amount of water in I is low (the water molecule has 0.074 occupancy, see Refinement section), it was difficult to evaluate the effect of water on the total lattice energy. However, it is clear that the presence of water makes the structure of I less densely packed.

Table 4
Crystal packing characteristics, components of lattice energy and total lattice energy (kJ mol⁻¹)

	I	II
Cell volume, Å	2694.5 (10)	1294.2 (9)
Density, g cm⁻³	1.406	1.464
Packing coefficient	0.739	0.771
Coulombic	−29.9	−35.5
Polarization	−40.2	−40.2
Dispersion	−147.4	−144.1
Repulsion	64.8	67.4
Total	−152.6	−152.3

6. Database survey

A search of the Cambridge Crystallographic Database (CSD version 5.40, update of September 2019; Groom et al., 2016 ) for the molecules with the same structure as isomers I and II gave no entries. Three entries were found for the same core structure as in the title molecules. (Adams & Morsi, 1976 ; Dey & Chopra, 2017; Shibakami & Sekiya, 1995 ). One is an inclusion compound of phenylbenzoate with Ni complexes with isonicotinic acid and thiocyanato coordination bridges (Sekiya et al., 2004 ). Several methyl-substituted phenylbenzoates have been described by Gowda and co-workers, in particular the 2,3-, 2,4- and 2,5-isomers (Gowda, Foro et al., 2008 ; Gowda et al., 2009 ). Compounds with the same core and nitro-group substituents are rare and are mostly limited to halogen-substituted phenylbenzoates. The dihedral angles between the two aromatic rings vary. The methyl-substituted compounds tend to have a near-perpendicular geometry with dihedral angles ranging from 73.04 (8) to 87.43 (5)° (Gowda, Tokarcík et al., 2008 ; Gowda et al., 2009), while pure phenylbenzoate and many of its fluorinated derivatives have angles in the range 52.66 (7) to 62.76 (4)° (Adams & Morsi, 1976; Dey & Chopra, 2017). The number of entries in the database for nitro-substituted phenylbenzoates is limited and is not sufficient for drawing final conclusions on the role of the nitro-group position on the molecular geometry (Saha & Desiraju, 2017). Finally, the presence of phenylbenzoate in inclusion compounds seems to have a `flattening' effect on the molecule, lowering the dihedral angle; such a compound was described by Sekiya et al. (2004) with a dihedral angle between the aromatic rings of 20.9 (19)°. Careful analysis of substituted phenyl benzoate derivatives (415 entries in the CSD) presented by Saha & Desiraju (2017) has shown a strong preference for Ar–Ar torsion angles of between 40 and 90° (91% of entries).

7. Synthesis and crystallization

The synthesis of isomers I and II was performed according to Barros & Silva (2006). Crystals of both compounds were grown by slow evaporation from ethanol solution.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. For both structures, the C-bound hydrogen atoms were freely refined. A large residual electron density peak was found for I. It was modelled as a partial water molecule. The O6 atom of the water molecule occupies a site on a crystallographic C₂ axis (Fig. 2). The water molecule was freely refined with a resulting occupation factor of 0.074 (2). The water H atoms were added geometrically taking into account the direction of potential hydrogen bonds in the structure of I.

Table 5
Experimental details

	I	II
Crystal data
Chemical formula	C₁₅H₁₁NO₅·0.07H₂O	C₁₅H₁₁NO₅
M_r	286.58	285.25
Crystal system, space group	Monoclinic, C2/c	Monoclinic, P2₁/c
Temperature (K)	150	100
a, b, c (Å)	26.225 (6), 7.9955 (17), 13.772 (3)	12.209 (5), 14.307 (6), 7.418 (3)
β (°)	111.080 (3)	92.815 (7)
V (Å³)	2694.5 (10)	1294.2 (9)
Z	8	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.11	0.11
Crystal size (mm)	0.21 × 0.18 × 0.12	0.15 × 0.15 × 0.1

Data collection
Diffractometer	Bruker APEXII CCD	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )	Multi-scan (SADABS, Bruker, 2016)
T_min, T_max	0.687, 0.746	0.650, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	22632, 4010, 2983	5087, 3620, 2913
R_int	0.056	0.016
(sin θ/λ)_max (Å⁻¹)	0.711	0.741

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.05	0.040, 0.122, 1.06
No. of reflections	4010	3620
No. of parameters	244	234
No. of restraints	4	0
H-atom treatment	Only H-atom coordinates refined	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24	0.43, −0.23
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT2017/1 (Sheldrick, 2015a ), SHELXL2017/1 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2020 ).

Supporting information

CCDC references: 2002786; 2002785

Crystal structure: contains datablocks I, II. DOI: https://doi.org/10.1107/S2056989020006295/dj2001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020006295/dj2001Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020006295/dj2001IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989020006295/dj2001Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989020006295/dj2001IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: Mercury (Macrae et al., 2020).

2-Acetylphenyl 4-nitrobenzoate 0.07-hydrate (I) top

Crystal data top

C₁₅H₁₁NO₅·0.07H₂O	F(000) = 1190
M_r = 286.58	D_x = 1.413 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.225 (6) Å	Cell parameters from 5275 reflections
b = 7.9955 (17) Å	θ = 2.7–29.6°
c = 13.772 (3) Å	µ = 0.11 mm⁻¹
β = 111.080 (3)°	T = 150 K
V = 2694.5 (10) Å³	Block, yellow
Z = 8	0.21 × 0.18 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	2983 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.056
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 30.4°, θ_min = 2.7°
T_min = 0.687, T_max = 0.746	h = −36→37
22632 measured reflections	k = −11→11
4010 independent reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	Only H-atom coordinates refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0487P)² + 1.2105P] where P = (F_o² + 2F_c²)/3
4010 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.28 e Å⁻³
4 restraints	Δρ_min = −0.24 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	Occ. (<1)
O1	0.35357 (3)	0.44264 (11)	0.29788 (7)	0.0308 (2)
O2	0.42547 (3)	0.33442 (12)	0.26638 (7)	0.0371 (2)
O5	0.40200 (4)	0.22975 (12)	0.45589 (8)	0.0418 (2)
O3	0.24003 (4)	−0.15624 (13)	−0.10893 (8)	0.0420 (2)
O4	0.17571 (4)	−0.07242 (14)	−0.05770 (8)	0.0455 (3)
N1	0.22348 (4)	−0.07748 (13)	−0.04993 (8)	0.0323 (2)
C6	0.42127 (4)	0.52092 (15)	0.46672 (9)	0.0271 (2)
C7	0.33704 (5)	0.21458 (15)	0.18295 (9)	0.0266 (2)
C1	0.38789 (5)	0.56226 (15)	0.36503 (9)	0.0280 (2)
C14	0.37775 (5)	0.33207 (15)	0.25404 (9)	0.0275 (2)
C10	0.26387 (5)	0.01845 (14)	0.03499 (9)	0.0281 (2)
C12	0.35454 (5)	0.11618 (16)	0.11749 (10)	0.0321 (3)
C15	0.42406 (5)	0.34790 (16)	0.51033 (10)	0.0304 (3)
C9	0.24572 (5)	0.10844 (16)	0.10176 (10)	0.0325 (3)
C5	0.45180 (5)	0.65194 (17)	0.52810 (10)	0.0327 (3)
C11	0.31776 (5)	0.01690 (16)	0.04198 (10)	0.0320 (3)
C8	0.28291 (5)	0.20799 (16)	0.17673 (10)	0.0313 (3)
C4	0.44849 (6)	0.81349 (17)	0.48991 (11)	0.0382 (3)
C2	0.38375 (6)	0.72310 (17)	0.32635 (11)	0.0355 (3)
C3	0.41424 (6)	0.84948 (17)	0.38984 (12)	0.0397 (3)
C13	0.45479 (7)	0.3244 (2)	0.62472 (11)	0.0419 (3)
O6	0.500000	0.0754 (11)	0.250000	0.040 (2)	0.148 (2)
H6	0.474 (2)	0.151 (3)	0.256 (8)	0.048*	0.148 (2)
H5	0.4747 (7)	0.626 (2)	0.5957 (13)	0.040 (4)*
H12	0.3931 (6)	0.1215 (19)	0.1236 (12)	0.038 (4)*
H13A	0.4407 (7)	0.398 (2)	0.6677 (14)	0.054 (5)*
H2	0.3589 (7)	0.745 (2)	0.2553 (14)	0.047 (4)*
H3	0.4122 (7)	0.961 (2)	0.3652 (13)	0.051 (5)*
H11	0.3295 (6)	−0.048 (2)	−0.0046 (12)	0.045 (4)*
H13B	0.4515 (7)	0.208 (2)	0.6428 (14)	0.057 (5)*
H9	0.2081 (7)	0.1025 (19)	0.0956 (12)	0.040 (4)*
H4	0.4692 (7)	0.901 (2)	0.5340 (13)	0.052 (5)*
H8	0.2717 (6)	0.273 (2)	0.2253 (12)	0.041 (4)*
H13C	0.4953 (9)	0.353 (3)	0.6436 (16)	0.074 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0267 (4)	0.0308 (4)	0.0320 (4)	−0.0018 (3)	0.0072 (3)	−0.0082 (4)
O2	0.0277 (4)	0.0466 (6)	0.0372 (5)	−0.0066 (4)	0.0119 (4)	−0.0124 (4)
O5	0.0580 (6)	0.0288 (5)	0.0387 (5)	−0.0050 (4)	0.0177 (5)	−0.0028 (4)
O3	0.0455 (5)	0.0399 (5)	0.0357 (5)	−0.0030 (4)	0.0085 (4)	−0.0104 (4)
O4	0.0296 (5)	0.0521 (6)	0.0491 (6)	−0.0116 (4)	0.0072 (4)	−0.0051 (5)
N1	0.0325 (5)	0.0279 (5)	0.0311 (5)	−0.0047 (4)	0.0050 (4)	0.0009 (4)
C6	0.0260 (5)	0.0281 (6)	0.0286 (6)	−0.0013 (4)	0.0116 (4)	−0.0052 (5)
C7	0.0277 (5)	0.0264 (5)	0.0256 (5)	−0.0025 (4)	0.0096 (4)	−0.0011 (4)
C1	0.0262 (5)	0.0282 (6)	0.0297 (6)	−0.0021 (4)	0.0101 (4)	−0.0067 (5)
C14	0.0285 (5)	0.0289 (6)	0.0243 (5)	−0.0018 (4)	0.0088 (4)	−0.0023 (4)
C10	0.0276 (5)	0.0243 (5)	0.0292 (6)	−0.0046 (4)	0.0064 (4)	−0.0012 (4)
C12	0.0261 (5)	0.0355 (6)	0.0358 (6)	−0.0024 (5)	0.0127 (5)	−0.0067 (5)
C15	0.0327 (6)	0.0312 (6)	0.0304 (6)	0.0023 (5)	0.0152 (5)	−0.0021 (5)
C9	0.0263 (6)	0.0346 (6)	0.0386 (7)	−0.0053 (5)	0.0139 (5)	−0.0032 (5)
C5	0.0312 (6)	0.0370 (7)	0.0309 (6)	−0.0041 (5)	0.0124 (5)	−0.0086 (5)
C11	0.0312 (6)	0.0316 (6)	0.0335 (6)	−0.0012 (5)	0.0120 (5)	−0.0070 (5)
C8	0.0303 (6)	0.0333 (6)	0.0336 (6)	−0.0038 (5)	0.0153 (5)	−0.0063 (5)
C4	0.0428 (7)	0.0335 (7)	0.0429 (8)	−0.0110 (6)	0.0212 (6)	−0.0148 (6)
C2	0.0390 (7)	0.0313 (6)	0.0354 (7)	0.0028 (5)	0.0125 (6)	−0.0002 (5)
C3	0.0508 (8)	0.0262 (6)	0.0471 (8)	−0.0023 (6)	0.0238 (7)	−0.0027 (6)
C13	0.0488 (8)	0.0444 (8)	0.0318 (7)	0.0086 (6)	0.0138 (6)	0.0034 (6)
O6	0.037 (5)	0.033 (5)	0.044 (5)	0.000	0.008 (4)	0.000

Geometric parameters (Å, º) top

O1—C1	1.4076 (14)	C15—C13	1.5010 (19)
O1—C14	1.3503 (14)	C9—C8	1.3879 (17)
O2—C14	1.2011 (14)	C9—H9	0.960 (16)
O5—C15	1.2154 (15)	C5—C4	1.386 (2)
O3—N1	1.2242 (15)	C5—H5	0.932 (17)
O4—N1	1.2192 (14)	C11—H11	0.960 (16)
N1—C10	1.4788 (15)	C8—H8	0.971 (16)
C6—C1	1.3981 (17)	C4—C3	1.378 (2)
C6—C15	1.4994 (18)	C4—H4	0.958 (18)
C6—C5	1.4022 (17)	C2—C3	1.3865 (19)
C7—C14	1.4928 (16)	C2—H2	0.976 (17)
C7—C12	1.3928 (17)	C3—H3	0.945 (18)
C7—C8	1.3922 (16)	C13—H13A	0.998 (19)
C1—C2	1.3813 (18)	C13—H13B	0.976 (19)
C10—C9	1.3801 (18)	C13—H13C	1.02 (2)
C10—C11	1.3818 (17)	O6—H6	0.941 (14)
C12—C11	1.3857 (17)	O6—H6ⁱ	0.941 (14)
C12—H12	0.985 (15)

C14—O1—C1	116.52 (9)	C8—C9—H9	121.2 (9)
O3—N1—C10	117.89 (10)	C6—C5—H5	117.4 (10)
O4—N1—O3	123.86 (11)	C4—C5—C6	121.56 (13)
O4—N1—C10	118.25 (11)	C4—C5—H5	121.1 (10)
C1—C6—C15	122.83 (10)	C10—C11—C12	117.74 (11)
C1—C6—C5	116.31 (11)	C10—C11—H11	121.6 (9)
C5—C6—C15	120.85 (11)	C12—C11—H11	120.7 (9)
C12—C7—C14	117.11 (10)	C7—C8—H8	119.4 (9)
C8—C7—C14	122.48 (11)	C9—C8—C7	119.71 (11)
C8—C7—C12	120.32 (11)	C9—C8—H8	120.9 (9)
C6—C1—O1	121.30 (11)	C5—C4—H4	119.9 (10)
C2—C1—O1	115.86 (11)	C3—C4—C5	120.25 (12)
C2—C1—C6	122.72 (11)	C3—C4—H4	119.9 (10)
O1—C14—C7	111.42 (10)	C1—C2—C3	119.19 (13)
O2—C14—O1	124.01 (11)	C1—C2—H2	119.0 (10)
O2—C14—C7	124.44 (11)	C3—C2—H2	121.8 (10)
C9—C10—N1	118.48 (10)	C4—C3—C2	119.95 (13)
C9—C10—C11	123.20 (11)	C4—C3—H3	119.2 (10)
C11—C10—N1	118.30 (11)	C2—C3—H3	120.9 (10)
C7—C12—H12	119.1 (9)	C15—C13—H13A	112.0 (10)
C11—C12—C7	120.47 (11)	C15—C13—H13B	108.9 (11)
C11—C12—H12	120.4 (9)	C15—C13—H13C	110.8 (11)
O5—C15—C6	121.75 (11)	H13A—C13—H13B	109.1 (15)
O5—C15—C13	120.46 (12)	H13A—C13—H13C	106.8 (16)
C6—C15—C13	117.79 (11)	H13B—C13—H13C	109.1 (15)
C10—C9—C8	118.44 (11)	H6—O6—H6ⁱ	99 (3)
C10—C9—H9	120.3 (9)

O1—C1—C2—C3	176.78 (11)	C14—C7—C8—C9	173.48 (12)
O3—N1—C10—C9	179.69 (11)	C10—C9—C8—C7	−0.10 (19)
O3—N1—C10—C11	1.29 (17)	C12—C7—C14—O1	167.74 (11)
O4—N1—C10—C9	0.32 (17)	C12—C7—C14—O2	−8.35 (19)
O4—N1—C10—C11	−178.08 (12)	C12—C7—C8—C9	−2.88 (19)
N1—C10—C9—C8	−175.42 (11)	C15—C6—C1—O1	1.58 (17)
N1—C10—C11—C12	175.74 (11)	C15—C6—C1—C2	177.36 (12)
C6—C1—C2—C3	0.8 (2)	C15—C6—C5—C4	−178.13 (12)
C6—C5—C4—C3	0.7 (2)	C9—C10—C11—C12	−2.58 (19)
C7—C12—C11—C10	−0.5 (2)	C5—C6—C1—O1	−177.11 (10)
C1—O1—C14—O2	−2.64 (17)	C5—C6—C1—C2	−1.33 (18)
C1—O1—C14—C7	−178.76 (10)	C5—C6—C15—O5	−173.02 (12)
C1—C6—C15—O5	8.35 (18)	C5—C6—C15—C13	7.54 (17)
C1—C6—C15—C13	−171.09 (12)	C5—C4—C3—C2	−1.3 (2)
C1—C6—C5—C4	0.58 (18)	C11—C10—C9—C8	2.9 (2)
C1—C2—C3—C4	0.5 (2)	C8—C7—C14—O1	−8.72 (16)
C14—O1—C1—C6	−77.59 (14)	C8—C7—C14—O2	175.18 (12)
C14—O1—C1—C2	106.36 (13)	C8—C7—C12—C11	3.2 (2)
C14—C7—C12—C11	−173.34 (12)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O2	0.94 (1)	1.98 (2)	2.912 (6)	173 (2)
C13—H13A···O2ⁱⁱ	0.998 (19)	2.638 (19)	3.594 (2)	160.6 (14)
C11—H11···O5ⁱⁱⁱ	0.960 (16)	2.600 (17)	3.4725 (17)	151.3 (12)

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

2-Acetylphenyl 2-nitrobenzoate (II) top

Crystal data top

C₁₅H₁₁NO₅	F(000) = 592
M_r = 285.25	D_x = 1.464 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.209 (5) Å	Cell parameters from 2439 reflections
b = 14.307 (6) Å	θ = 2.2–31.6°
c = 7.418 (3) Å	µ = 0.11 mm⁻¹
β = 92.815 (7)°	T = 100 K
V = 1294.2 (9) Å³	Prism, yellow
Z = 4	0.15 × 0.15 × 0.1 mm

Data collection top

Bruker APEXII CCD diffractometer	2913 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.016
Absorption correction: multi-scan (SADABS, Bruker, 2016)	θ_max = 31.8°, θ_min = 1.7°
T_min = 0.650, T_max = 0.746	h = −17→16
5087 measured reflections	k = −20→14
3620 independent reflections	l = −3→10

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.122	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0675P)² + 0.172P] where P = (F_o² + 2F_c²)/3
3620 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C6	0.65734 (8)	0.01262 (7)	0.45205 (14)	0.0158 (2)
O1	0.79222 (6)	−0.00491 (5)	0.70582 (10)	0.01756 (18)
O3	0.84475 (8)	−0.14564 (6)	0.97495 (13)	0.0314 (2)
C5	0.60515 (9)	−0.03010 (8)	0.30108 (16)	0.0193 (2)
O5	0.67276 (8)	0.15066 (6)	0.63086 (13)	0.0319 (2)
C12	0.88232 (8)	−0.00579 (7)	1.12279 (15)	0.0166 (2)
N1	0.89918 (7)	−0.10690 (6)	1.09597 (14)	0.0207 (2)
C7	0.80754 (8)	0.04285 (7)	1.00989 (15)	0.0164 (2)
C8	0.79381 (9)	0.13811 (7)	1.04287 (17)	0.0214 (2)
C1	0.73215 (8)	−0.04200 (7)	0.55600 (14)	0.0160 (2)
O2	0.64412 (7)	−0.02330 (6)	0.87287 (12)	0.0282 (2)
C2	0.75414 (9)	−0.13411 (7)	0.51264 (16)	0.0201 (2)
C14	0.73772 (8)	−0.00042 (7)	0.86012 (15)	0.0174 (2)
C11	0.94230 (9)	0.03733 (8)	1.26288 (16)	0.0212 (2)
C3	0.69989 (10)	−0.17469 (8)	0.36297 (17)	0.0237 (2)
O4	0.96613 (8)	−0.14724 (7)	1.19635 (15)	0.0395 (3)
C15	0.63287 (9)	0.11279 (7)	0.49603 (16)	0.0191 (2)
C4	0.62600 (10)	−0.12258 (8)	0.25762 (16)	0.0226 (2)
C13	0.55711 (10)	0.16657 (8)	0.36771 (19)	0.0268 (3)
C10	0.92771 (10)	0.13212 (9)	1.29225 (18)	0.0258 (3)
C9	0.85407 (10)	0.18239 (8)	1.18253 (18)	0.0255 (3)
H2	0.8073 (13)	−0.1705 (11)	0.587 (2)	0.035 (4)*
H8	0.7406 (12)	0.1752 (10)	0.968 (2)	0.028 (4)*
H11	0.9935 (13)	0.0017 (11)	1.333 (2)	0.032 (4)*
H5	0.5541 (13)	0.0044 (10)	0.226 (2)	0.031 (4)*
H13A	0.4825 (13)	0.1366 (11)	0.359 (2)	0.040 (4)*
H10	0.9702 (14)	0.1641 (12)	1.387 (2)	0.043 (5)*
H4	0.5886 (13)	−0.1483 (11)	0.149 (2)	0.039 (4)*
H3	0.7153 (12)	−0.2407 (11)	0.337 (2)	0.033 (4)*
H9	0.8436 (13)	0.2498 (12)	1.199 (2)	0.041 (4)*
H13B	0.5874 (14)	0.1732 (12)	0.248 (2)	0.048 (5)*
H13C	0.5493 (16)	0.2303 (14)	0.415 (3)	0.061 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C6	0.0176 (4)	0.0157 (4)	0.0141 (5)	−0.0014 (3)	−0.0002 (4)	0.0012 (3)
O1	0.0176 (3)	0.0212 (4)	0.0135 (4)	−0.0011 (3)	−0.0029 (3)	−0.0015 (3)
O3	0.0479 (5)	0.0180 (4)	0.0272 (5)	−0.0031 (4)	−0.0111 (4)	−0.0016 (3)
C5	0.0222 (5)	0.0208 (5)	0.0145 (6)	−0.0019 (4)	−0.0033 (4)	0.0015 (4)
O5	0.0454 (5)	0.0182 (4)	0.0307 (6)	0.0037 (4)	−0.0132 (4)	−0.0063 (3)
C12	0.0171 (4)	0.0169 (5)	0.0155 (5)	0.0000 (3)	−0.0006 (4)	0.0006 (4)
N1	0.0220 (4)	0.0186 (4)	0.0213 (5)	0.0013 (3)	−0.0006 (4)	0.0030 (3)
C7	0.0178 (4)	0.0180 (5)	0.0133 (5)	−0.0013 (3)	−0.0016 (4)	0.0003 (3)
C8	0.0252 (5)	0.0185 (5)	0.0201 (6)	0.0016 (4)	−0.0030 (4)	0.0003 (4)
C1	0.0171 (4)	0.0178 (5)	0.0129 (5)	−0.0010 (3)	−0.0003 (4)	−0.0004 (4)
O2	0.0227 (4)	0.0441 (5)	0.0177 (5)	−0.0094 (3)	−0.0019 (3)	−0.0001 (4)
C2	0.0243 (5)	0.0173 (5)	0.0186 (6)	0.0030 (4)	−0.0006 (4)	0.0010 (4)
C14	0.0197 (5)	0.0180 (5)	0.0141 (6)	0.0003 (4)	−0.0040 (4)	0.0016 (4)
C11	0.0195 (5)	0.0262 (5)	0.0174 (6)	0.0004 (4)	−0.0048 (4)	−0.0003 (4)
C3	0.0340 (6)	0.0169 (5)	0.0202 (6)	0.0003 (4)	0.0019 (5)	−0.0032 (4)
O4	0.0411 (5)	0.0269 (5)	0.0484 (7)	0.0120 (4)	−0.0185 (5)	0.0045 (4)
C15	0.0210 (5)	0.0153 (5)	0.0207 (6)	−0.0008 (4)	−0.0006 (4)	0.0024 (4)
C4	0.0311 (5)	0.0211 (5)	0.0152 (6)	−0.0044 (4)	−0.0029 (4)	−0.0029 (4)
C13	0.0288 (6)	0.0190 (5)	0.0319 (7)	0.0034 (4)	−0.0064 (5)	0.0058 (5)
C10	0.0267 (5)	0.0291 (6)	0.0209 (7)	−0.0042 (4)	−0.0052 (5)	−0.0079 (5)
C9	0.0314 (6)	0.0193 (5)	0.0256 (7)	−0.0013 (4)	−0.0004 (5)	−0.0052 (4)

Geometric parameters (Å, º) top

C6—C5	1.4014 (16)	C1—C2	1.3860 (15)
C6—C1	1.4036 (15)	O2—C14	1.1969 (14)
C6—C15	1.5031 (15)	C2—C3	1.3914 (17)
O1—C1	1.4053 (13)	C2—H2	0.981 (16)
O1—C14	1.3534 (14)	C11—C10	1.3865 (17)
O3—N1	1.2232 (13)	C11—H11	0.941 (16)
C5—C4	1.3884 (17)	C3—C4	1.3824 (18)
C5—H5	0.954 (15)	C3—H3	0.984 (16)
O5—C15	1.2179 (15)	C15—C13	1.5057 (17)
C12—N1	1.4762 (15)	C4—H4	0.981 (17)
C12—C7	1.3943 (15)	C13—H13A	1.006 (16)
C12—C11	1.3864 (16)	C13—H13B	0.986 (18)
N1—O4	1.2230 (13)	C13—H13C	0.98 (2)
C7—C8	1.3961 (16)	C10—C9	1.3843 (19)
C7—C14	1.5004 (15)	C10—H10	0.969 (17)
C8—C9	1.3932 (17)	C9—H9	0.981 (17)
C8—H8	0.987 (15)

C5—C6—C1	117.02 (9)	O2—C14—O1	124.38 (10)
C5—C6—C15	120.13 (10)	O2—C14—C7	124.35 (10)
C1—C6—C15	122.85 (10)	C12—C11—C10	119.06 (11)
C14—O1—C1	115.32 (8)	C12—C11—H11	118.9 (9)
C6—C5—H5	120.0 (9)	C10—C11—H11	122.0 (9)
C4—C5—C6	121.32 (11)	C2—C3—H3	118.0 (9)
C4—C5—H5	118.7 (9)	C4—C3—C2	119.87 (10)
C7—C12—N1	119.98 (9)	C4—C3—H3	122.2 (9)
C11—C12—N1	117.71 (9)	C6—C15—C13	118.20 (10)
C11—C12—C7	122.30 (10)	O5—C15—C6	121.78 (10)
O3—N1—C12	117.94 (9)	O5—C15—C13	120.02 (10)
O4—N1—O3	123.77 (10)	C5—C4—H4	117.8 (9)
O4—N1—C12	118.29 (10)	C3—C4—C5	120.31 (11)
C12—C7—C8	117.55 (10)	C3—C4—H4	121.9 (9)
C12—C7—C14	124.77 (9)	C15—C13—H13A	110.4 (9)
C8—C7—C14	117.64 (10)	C15—C13—H13B	112.0 (10)
C7—C8—H8	120.5 (8)	C15—C13—H13C	108.5 (11)
C9—C8—C7	120.71 (11)	H13A—C13—H13B	111.2 (14)
C9—C8—H8	118.8 (8)	H13A—C13—H13C	108.4 (15)
C6—C1—O1	121.64 (9)	H13B—C13—H13C	106.1 (15)
C2—C1—C6	122.01 (10)	C11—C10—H10	120.5 (10)
C2—C1—O1	116.30 (9)	C9—C10—C11	120.04 (11)
C1—C2—C3	119.46 (10)	C9—C10—H10	119.5 (10)
C1—C2—H2	120.3 (9)	C8—C9—H9	118.1 (10)
C3—C2—H2	120.3 (9)	C10—C9—C8	120.33 (11)
O1—C14—C7	111.15 (9)	C10—C9—H9	121.5 (10)

C6—C5—C4—C3	−0.37 (17)	C8—C7—C14—O2	−79.61 (14)
C6—C1—C2—C3	−0.77 (16)	C1—C6—C5—C4	0.55 (16)
O1—C1—C2—C3	−178.27 (9)	C1—C6—C15—O5	−3.97 (16)
C5—C6—C1—O1	177.39 (9)	C1—C6—C15—C13	175.80 (10)
C5—C6—C1—C2	0.02 (15)	C1—O1—C14—C7	−178.19 (8)
C5—C6—C15—O5	176.43 (10)	C1—O1—C14—O2	−1.95 (15)
C5—C6—C15—C13	−3.80 (15)	C1—C2—C3—C4	0.95 (17)
C12—C7—C8—C9	0.76 (16)	C2—C3—C4—C5	−0.40 (18)
C12—C7—C14—O1	−85.81 (12)	C14—O1—C1—C6	81.05 (12)
C12—C7—C14—O2	97.95 (14)	C14—O1—C1—C2	−101.44 (11)
C12—C11—C10—C9	0.02 (18)	C14—C7—C8—C9	178.50 (10)
N1—C12—C7—C8	179.17 (9)	C11—C12—N1—O3	178.49 (10)
N1—C12—C7—C14	1.61 (15)	C11—C12—N1—O4	−1.10 (15)
N1—C12—C11—C10	−179.57 (10)	C11—C12—C7—C8	−0.38 (15)
C7—C12—N1—O3	−1.08 (14)	C11—C12—C7—C14	−177.94 (10)
C7—C12—N1—O4	179.33 (10)	C11—C10—C9—C8	0.36 (18)
C7—C12—C11—C10	−0.01 (16)	C15—C6—C5—C4	−179.82 (10)
C7—C8—C9—C10	−0.76 (18)	C15—C6—C1—O1	−2.23 (15)
C8—C7—C14—O1	96.63 (11)	C15—C6—C1—C2	−179.60 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.941 (16)	2.646 (15)	3.2711 (19)	124.4 (12)

Symmetry code: (i) −x+2, −y, −z+2.

Comparison of conformational characteristics (°) of isomers I and II from diffraction (X-ray) and computational (DFT) data top

Conformational parameters	Isomer I – X-ray	Isomer I – DFT	Isomer II – X-ray	Isomer II – DFT
C9—C10—N1—O4	0.32 (17)	0.14	–	–
C11—C12—N1—O4	–	–	-1.10 (15)	-21.06
C5—C6—C15—C13	7.54 (17)	6.03	-3.80 (15)	-10.18
C12—C7—C14—O1	167.74 (11)	172.87	-85.81 (12)	-65.72
C7—C14—O1—C1	-178.76 (10)	171.54	-178.19 (8)	-175.37
C6—C1—O1—C14	-77.59 (14)	-77.23	81.05 (12)	82.74
Ar/Ar	84.80 (4)	87.03	6.12 (7)	21.04

Crystal packing characteristics, components of lattice energy and total lattice energy (kJ mol^-1) top

	I	II
Cell volume, Å	2694.5 (10)	1294.2 (9)
Density, g cm^-3	1.406	1.464
Packing coefficient	0.739	0.771
Coulombic	-29.9	-35.5
Polarization	-40.2	-40.2
Dispersion	-147.4	-144.1
Repulsion	64.8	67.4
Total	-152.6	-152.3

Funding information

Funding for this research was provided by: National Science Foundation (grant No. DMR-1523611).

References

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Volume 76| Part 6| June 2020| Pages 857-861

https://doi.org/10.1107/S2056989020006295

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

Mol­ecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitro­benzo­yl­oxy)aceto­phenone isomers

1. Chemical context

2. Structural commentary

3. DFT calculations

4. Supra­molecular features

5. Lattice energy calculations

6. Database survey

7. Synthesis and crystallization

8. Refinement

Supporting information

Funding information

References

research communications

Molecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitrobenzoyloxy)acetophenone isomers

4. Supramolecular features