Crystal structures of three functionalized chalcones: 4′-di­methyl­amino-3-nitro­chalcone, 3-di­methyl­amino-3′-nitrochalcone and 3′-nitro­chalcone

Hall, C.L.; Hamilton, V.; Potticary, J.; Cremeens, M.E.; Pridmore, N.E.; Sparkes, H.A.; D'ambruoso, G.D.; Warren, S.D.; Matsumoto, M.; Hall, S.R.

doi:10.1107/S2056989020011858

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ISSN: 2056-9890

Volume 76| Part 10| October 2020| Pages 1599-1604

https://doi.org/10.1107/S2056989020011858

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Crystal structures of three functionalized chalcones: 4′-dimethylamino-3-nitrochalcone, 3-dimethylamino-3′-nitrochalcone and 3′-nitrochalcone

^aSchool of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, England, and ^bDepartment of Chemistry & Biochemistry, Gonzaga University, 502 E Boone Ave, Spokane, WA 99258, USA
^*Correspondence e-mail: simon.hall@bristol.ac.uk

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 9 July 2020; accepted 27 August 2020; online 4 September 2020)

The structure of three functionalized chalcones (1,3-diarylprop-2-en-1-ones), containing combinations of nitro and dimethylamino functional groups, are presented, namely, 1-[4-(dimethylamino)phenyl]-3-(3-nitrophenyl)prop-2-en-1-one, C₁₇H₁₆N₂O₃, Gp8m, 3-[3-(dimethylamino)phenyl]-1-(3-nitrophenyl)prop-2-en-1-one, C₁₇H₁₆N₂O₃, Hm7m and 1-(3-nitrophenyl)-3-phenylprop-2-en-1-one, C₁₅H₁₁NO₃, Hm1-. Each of the molecules contains bonding motifs seen in previously solved crystal structures of functionalized chalcones, adding to the large dataset available for these small organic molecules. The structures of all three of the title compounds contain similar bonding motifs, resulting in two-dimensional planes of molecules formed via C—H⋯O hydrogen-bonding interactions involving the nitro- and ketone groups. The structure of Hm1- is very similar to the crystal structure of a previously solved isomer [Jing (2009 ). Acta Cryst. E65, o2510].

Keywords: chalcone; dimethylamino; nitro; crystal structure.

CCDC references: 2025821; 2025820; 2025819

1. Chemical context

Chalcones, 1,3-diarylprop-2-en-1-ones, are a group of organic molecules containing two aromatic rings joined by an enone backbone. Chalcones are studied for a range of medicinal purposes, with many reviews published on their biological applicability (see, for example, Rammohan et al., 2020 ; Zhuang et al., 2017 ; Singh et al., 2014 ).

A range of chalcones, functionalized on either aromatic ring, can be readily synthesized via an aldol condensation reaction (Mandge et al., 2007 ). Altering the functional groups on the chalcone structure has been shown to yield a variety of useful properties, including changes in colour and fluorescent properties (Ibnaouf et al., 2018 ).

In this work, the structures of three chalcones: 4′-dimethylamino-3-nitrochalcone [Gp8m, R₁ = N(CH₃)₂, R₂ = H, R₃ = NO₂], 3′-nitro-3-dimethylaminochalcone [Hm7m, R₁ = NO₂, R₂ = N(CH₃)₂, R₃ = H] and 3′-nitrochalcone [Hm1-, R₁ = NO₂, R₂ = H, R₃ = H] are presented. The crystal structures of these molecules add to the large dataset available for molecules based on the chalcone backbone. In particular, these structures add to the small amount of data available for chalcones substituted with a nitro group on the 3-ring.

2. Structural commentary

The planarity of the chalcone molecules is defined by the torsion angles Φ₁ = C5—C4—C1—C2, Φ₂ = C4—C1—C2—C3 and Φ₃ = C2—C3—C10—C11. The torsion angle C1—C2—C3—C10 is planar to within 1° of 180° in all three structures. The torsion angles, along with the numbering of the molecules, are highlighted in the scheme. The 1-ring of the molecule is defined as the aromatic ring attached to C1 and the 3-ring is that attached to C3. The long axis of each molecule is defined to be along the C2–C12 axis, and the short axis is defined to be along H2–C2. Table 1 presents a summary of the torsion and ring angles in the title structures.

Table 1
Torsion and ring angles (°) describing the planarity of molecules in each crystal structure

Torsion angles calculated using the definitions: Φ₁ = C5—C4—C1—C2, Φ₂ = C4—C1—C2—C3 and Φ₃ = C2—C3—C10—C11. Ring twist and fold angles were calculated using the mean planes of the 1- and 3-rings. All values were calculated using OLEX2 (Dolomanov et al., 2009 ).

	Gm8p	Hm7m	Hm1- (1)	Hm1- (2)
Φ₁	−173.15 (11)	172.9 (2)	177.4 (2)	−164.6 (2)
Φ₂	158.84 (12)	168.8 (2)	174.4 (2)	175.9 (2)
Φ₃	−169.23 (13)	−175.0 (2)	−170.3 (3)	−172.9 (9)
Ring twist angle	3.61 (4)	13.8 (8)	1.88 (8)	12.58 (8)
Ring fold angle	11.46 (4)	0.59 (8)	2.58 (8)	6.66 (8)

Gp8m (Fig. 1a) crystallizes in space group P2₁/c with a single molecule in the asymmetric unit. The molecule deviates from planarity, with Φ₂ = 158.84 (12)°, meaning that there is a fold angle of 11.46 (4)° between the planes of the 1- and 3- rings of the molecule. The nitro group on the 3-ring is twisted out of the plane of the ring [C11—C12—N2—O2 = 10.09 (18)°].

Figure 1
Displacement ellipsoid plots showing the asymmetric units of the solved crystal structures (a) Gp8m, (b) Hm7m and (c) Hm1-. Displacement ellipsoids are shown at the 50% probability level. The stacking interaction between the 1- and 3-rings of the molecules in the asymmetric unit of Hm1- is highlighted.

Hm7m (Fig. 1b) crystallizes in space group P2₁/n with a single molecule in the asymmetric unit. The combination of torsion angles along the long-axis of the molecule means that although the backbone remains relatively planar [C4—C10—C2 = 2.86 (6)°], the 1- and 3-rings are twisted with respect to each other, with a twist angle of 13.80 (8)° between the planes of the rings.

Hm1- crystallizes in space group P2₁/c and contains two molecules in the asymmetric unit. One of the molecules (1) is almost planar, with a twist angle of only 1.88 (8)° between the planes of the 1- and 3-rings of the molecule. The second molecule (2) is less planar with Φ₁ = −164.6 (2) and Φ₂ = −172 (9)°, leading to a twist angle of 12.85 (8)° between the planes of the 1- and 3-rings. There is a stacking interaction between the aryl rings of the two molecules in the asymmetric unit, with a centroid-to-centroid distance of 3.82782 (17) Å (Fig. 1c).

In each of the molecular structures, the functionalized group in the meta-position sits on the same side of the molecule as the carbonyl oxygen group (1-ring: C6, 3-ring: C12). This is likely due to the optimization of hydrogen-bonding motifs in the crystal structures.

3. Supramolecular features

Although being in a different space group, the crystal structure of Gp8m is very similar to that of a previously reported chalcone 3′-nitro,4-dimethylaminochalcone (Rosli et al., 2007 ). This may be expected, as the only difference between these molecules is that the functional groups are on opposite rings. Within the crystal structure, chains of molecules form down the long axis of the molecule via short contacts between the dimethylamino and nitro groups (Fig. 2a; C17—H17B⋯O3ⁱⁱⁱ). These molecules form stacks parallel to the b axis, with alternate molecules the opposite way around such that the nitro group sits above the 1-ring of the adjacent molecule. The final 3D structure is completed by a linking of the stacks via C—H⋯O cyclic hydrogen bonding (C3—H3⋯O1ⁱ, C5—H5⋯O2ⁱ, C11—H11⋯O1ⁱ) and hydrogen bonds involving the carbonyl group (Fig. 2b; C15—H15⋯O1ⁱⁱ). Numerical details of the hydrogen-bond geometry and symmetry codes are given in Table 2.

Table 2
Hydrogen-bond geometry (Å, °) for Gp8m

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.47	3.3124 (16)	148
C5—H5⋯O2ⁱ	0.95	2.67	3.3067 (17)	125
C11—H11⋯O1ⁱ	0.95	2.88	3.5773 (16)	131
C15—H15⋯O1ⁱⁱ	0.95	2.68	3.5435 (16)	152
C17—H17B⋯O3ⁱⁱⁱ	0.98	2.68	3.5755 (17)	152
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Figure 2
Bonding motifs present in the crystal structure of Gp8m. (a) Interactions in the plane of the rings of the molecules. (b) Hydrogen bonds offset along the short axis of the molecule. Cyclic hydrogen bonds highlighted in (a) are shown in green and an additional hydrogen-bonding motif is shown in blue. Stacking interactions are highlighted in red. [Symmetry codes: (i) −x + 1, −y + 1, −z; (ii) x,-y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ; (iii) x − 1, y, z; (iv) −x + 1, y + $[{1\over 2}]$ , −z − $[{1\over 2}]$ ; (v) −x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (vi) x, −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ .]

Within the crystal structure of Hm7m, sheets are formed in the plane of the aromatic rings of the molecule. Within the plane, pairs of inverted molecules form via cyclic hydrogen bonding between the dimethylamino and nitro groups, offset in the short axis of the molecule (C16—H16B⋯O2ⁱⁱ). The pairs of molecules then form sheets via a trifurcated hydrogen-bonding interaction involving the nitro group (C15—H15⋯O3ⁱ, C15—H2⋯O3ⁱ, C15—H9⋯O3ⁱ). These sheets make up the 3D structure via a stacking interaction, where the nitro group of one molecule sits over the 1- ring of another (Fig. 3). Numerical details of the hydrogen-bond geometry and symmetry codes are given in Table 3.

Table 3
Hydrogen-bond geometry (Å, °) for Hm7m

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3ⁱ	0.95	2.50	3.442 (2)	174
C16—H16B⋯O2ⁱⁱ	0.98	2.58	3.520 (2)	160
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Figure 3
Bonding motifs present in the crystal structure of Hm7m. Two sheets of molecules are highlighted, coloured in black and light blue for contrast. [Symmetry codes: (i) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) −x, −y + 1, −z + 1; (iii) −x + 1, −y + 1, −z + 1.]

The crystal structure of Hm1- contains two molecules in the asymmetric unit cell, which differ slightly in their planarity. Sheets of molecules form via the same interactions as in Hm7m; however, the pairs of molecules form between different independent molecules, meaning they are not directly related by an inversion centre. Furthermore, the absence of the dimethylamino group means that the molecules are shifted relatively along the long axis of the molecule, forming hydrogen bonds that utilize the carbonyl oxygen (Fig. 4a). The stacking interactions that make up the 3D structure of Hm1- are more complex than those in Hm7m, and are highlighted in Fig. 4b. Molecule 1 forms a direct stack with a symmetrically equivalent molecule, with an inversion centre relating the molecules. There is a half stack that forms between the 1-ring of molecule 1 and the 3-ring of molecule 2, which sit at approximately 90° to each other. Finally, molecule 2 forms a half stack with a symmetrically equivalent molecule, where the 1-ring of each molecule sits on top of the other. Numerical details of the hydrogen-bond geometry are given in Table 4.

Table 4
Hydrogen-bond geometry (Å, °) for Hm1-

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.95	2.51	3.456 (3)	174
C3—H3⋯O4ⁱⁱ	0.95	2.50	3.328 (3)	146
C9—H9⋯O3ⁱ	0.95	2.58	3.527 (3)	175
C15—H15⋯O3ⁱ	0.95	2.47	3.399 (3)	166
C17—H17⋯O6ⁱⁱⁱ	0.95	2.57	3.491 (3)	164
C18—H18⋯O1^iv	0.95	2.46	3.300 (3)	147
C30—H30⋯O6ⁱⁱⁱ	0.95	2.58	3.456 (3)	154
C26—H26⋯O1^iv	0.95	2.54	3.328 (3)	140
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 4
Bonding motifs present in the crystal structure of Hm1-. (a) Hydrogen-bonding interactions forming two-dimensional planes of molecules. (b) Stacking interactions present in the crystal structure. Molecules are coloured according to their symmetry equivalence as green (1) and blue (2). [Symmetry codes: (i) −x, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) x, −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; (v) −x, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (vi) −x + 1, −y + 1, −z + 2; (vii) −x + 1, −y, −z + 2; (viii) −x, −y, −z + 1; (ix) −x + 1, −y + 1, −z + 1.]

4. Database survey

A survey of the Cambridge Structural Database (CSD, version 5.41, last update March 2020; Groom et al., 2016 ) revealed 38 structures of chalcones functionalized with either nitro or dimethylamino-groups in either the meta or para positions of the 1- or 3-ring. None of the structures contain chalcones with a dimethylamino group on the 1- ring, as in Gp8m. However, there are 14 structures of chalcones substituted with a dimethylamino group on the 3-ring, likely owing to their fluorescent properties (Jiang et al., 1994 ; Tomasch et al., 2012 ).

17 of the 29 structures that contain nitro ring substitutions contain the bonding motif between the nitro group and the region between H15, H2 and H9, as observed in Hm7m and Hm1-. This is likely caused by the optimization of electrostatic interactions, as highlighted by the electrostatic potentials in Fig. 5. The layered motif in Hm7m is the same as that present in the structure of 3′-nitro-3,5-dimethoxychalcone (Qiu & Yang, 2006 ). The planes of molecules seen in Hm1- are similar to those seen in the structure of 4′-nitrochalcone (BUDXOO; Jing, 2009).

Figure 5
Electrostatic potential maps for optimized configurations of Gp8m, Hm7m and Hm1- molecules. Optimizations were carried out using Gaussian09 [B3LYP/6–31 G(d); Frisch et al., 2009

]. The electrostatic potential is mapped onto the 0.0004 SCF electron density surface.

5. Synthesis and crystallization

Each of the functionalized chalcones was synthesized via an aldol condensation reaction between a suitably functionalized benzaldehyde and acetophenone. While syntheses were not specifically reported for Gp8m and Hm7m, the first reports for Hm1- appeared in 1929 and 1935 (Dilthey et al., 1929 ; Weygand et al., 1935 ).

Ethanol (1.5 mL, 95%) and a stir bar were added to two separate vessels; one contained the benzaldehyde (3 mmol) and the other contained the acetophenone (3 mmol). Each vessel was gently heated over a hot plate until complete dissolution and then cooled to room temperature; depending on the solubility of the starting materials, solids precipitated upon cooling. Once cooled, NaOH (aq) (0.4 mL, 50% by wgt) was added to the vessel containing the acetophenone and vigorously stirred. The benzaldehyde mixture was added to the acetophenone and NaOH mixture. The resulting reaction mixture was vigorously mixed until a slurry or paste formed. Water was added to the vessel and the contents were agitated with a micro spatula. The solids were collected by vacuum filtration and purified by recrystallization with ethanol. ¹H NMR (400 MHz, CDCl₃, referenced to TMS): δ (ppm) for Gp8m are 8.51 (1H, s), 8.22 (1H, d, J = 8.0 Hz), 8.02 (2H, d, J = 8.9 Hz), 7.90 (1H, d, J = 7.5 Hz), 7.79 (1H, d, J = 15.6 Hz), 7.70 (1H, d, J = 15.6 Hz), 7.59 (1H, t, J = 8.0 Hz), 6.72 (2H, d, J = 8.9 Hz), 3.11 (6H, s); for Hm1- are 8.83 (1H, t, J = 1.9 Hz), 8.44 (1H, ddd, J = 8.2, 2.2, 1.0 Hz), 8.35 (1H, ddd, J = 7.8, 1.4, 1.4 Hz), 7.89 (1H, d, J = 15.6 Hz), 7.72 (1H, t, J = 8.0 Hz), 7.67 (2H, m), 7.54 (1H, d, J = 15.6 Hz), 7.45 (3H, m); and for Hm7m are 8.82 (1H, t, J = 1.9 Hz), 8.42 (1H, ddd, J = 8.2, 2.2, 1.0 Hz), 8.34 (1H, ddd, J = 7.7, 1.2, 1.2 Hz), 7.85 (1H, d, J = 15.6 Hz), 7.71 (1H, t, J = 8.0 Hz), 7.48 (1H, d, J = 15.6 Hz), 7.30 (1H, t, J = 7.9 Hz), 7.06 (1H, d, J = 7.6 Hz), 6.92 (1H, dd, J = 2.1, 1.6 Hz), 6.82 (1H, dd, J = 8.2, 2.5 Hz). ¹³C NMR (100 MHz, CDCl₃, referenced to solvent, 77.16 ppm): δ (ppm) for Gp8m are 186.86, 153.82, 148.83, 139.52, 137.49, 134.45, 131.16, 130.03, 125.51, 125.05, 124.21, 122.14, 111.02, 40.21; for Hm7m are 188.41, 150.97, 148.49, 148.27, 139.79, 135.06, 134.23, 129.96, 129.79, 127.02, 123.39, 120.42, 116.63, 115.42, 112.82, 40.60; and for Hm1- are 188.09, 148.50, 146.87, 139.58, 134.40, 134.22, 131.33, 130.04, 129.21, 128.86, 127.18, 123.37, 120.72.

Crystals of Hm7m suitable for structural solution via single crystal X-ray diffraction were produced via evaporation of a 10 mg mL⁻¹ acetone solution. Crystals of three separate colours were observed (yellow needles, orange needles and red block-like crystals); however, only crystals of a red block-like morphology were suitable for structure solution. Hm7m appeared to go through a phase transition between 100 K and 200 K which caused the crystal to crack. For this reason, single crystal X-ray diffraction was carried out at 200 K.

Crystals of Hm1- and Gp8m suitable for structural solution via single crystal X-ray diffraction were produced via evaporation of an ethanol solution of concentration 10 mg mL⁻¹. Crystals of Gp8m appeared as fine yellow needles and Hm1- as colourless block-like crystals. Each single crystal was mounted onto a glass capillary using paraffin oil.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. All hydrogen atoms were located geometrically (aromatic C—H = 0.95 Å, methyl C—H = 0.99 Å) and refined using a riding model [U_iso(H) = 1.2U_eq(C-aromatic) or 1.5U_eq(C-methyl)].

Table 5
Experimental details

	Hm1-	Gp8m	Hm7m
Crystal data
Chemical formula	C₁₅H₁₁NO₃	C₁₇H₁₆N₂O₃	C₁₇H₁₆N₂O₃
M_r	253.25	296.32	296.32
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/n
Temperature (K)	100	100	200
a, b, c (Å)	14.7856 (8), 15.9841 (9), 10.3188 (6)	17.3171 (7), 7.0708 (3), 11.3487 (4)	7.7552 (4), 15.6998 (7), 12.0525 (7)
β (°)	99.210 (4)	90.761 (3)	100.668 (3)
V (Å³)	2407.3 (2)	1389.48 (10)	1442.09 (13)
Z	8	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.10	0.10	0.10
Crystal size (mm)	0.61 × 0.35 × 0.25	0.39 × 0.35 × 0.19	0.39 × 0.33 × 0.25

Data collection
Diffractometer	Bruker APEXII Kappa CCD area detector	Bruker APEXII Kappa CCD area detector	Bruker APEXII Kappa CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )	Multi-scan (SADABS; Bruker, 2016)	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.610, 0.746	0.666, 0.746	0.629, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	25080, 4408, 2657	12270, 3320, 2561	11497, 3056, 1882
R_int	0.085	0.034	0.058
(sin θ/λ)_max (Å⁻¹)	0.602	0.659	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.141, 0.99	0.043, 0.123, 1.04	0.049, 0.133, 1.02
No. of reflections	4408	3320	3056
No. of parameters	343	212	201
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25	0.31, −0.28	0.19, −0.24
Computer programs: APEX2 (Bruker, 2016), SAINT (Bruker, 2016), SUPERFLIP (Palatinus & Chapuis, 2007 ; Palatinus & van der Lee, 2008 ; Palatinus et al., 2012 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020 ), OLEX2 (Dolomanov et al., 2009).

Supporting information

CCDC references: 2025821; 2025820; 2025819

Crystal structure: contains datablocks Hm1-, global, Gp8m, Hm7m. DOI: https://doi.org/10.1107/S2056989020011858/dx2030sup1.cif

Structure factors: contains datablock Gp8m. DOI: https://doi.org/10.1107/S2056989020011858/dx2030Gp8msup2.hkl

Structure factors: contains datablock Hm7m. DOI: https://doi.org/10.1107/S2056989020011858/dx2030Hm7msup3.hkl

Structure factors: contains datablock Hm1-. DOI: https://doi.org/10.1107/S2056989020011858/dx2030Hm1-sup4.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989020011858/dx2030Gp8msup5.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989020011858/dx2030Hm7msup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989020011858/dx2030Hm1-sup7.cml

checkCIF report

Computing details top

For all structures, data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-[4-(Dimethylamino)phenyl]-3-(3-nitrophenyl)prop-2-en-1-one (Gp8m) top

Crystal data top

C₁₇H₁₆N₂O₃	F(000) = 624
M_r = 296.32	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.3171 (7) Å	Cell parameters from 2510 reflections
b = 7.0708 (3) Å	θ = 2.4–27.7°
c = 11.3487 (4) Å	µ = 0.10 mm⁻¹
β = 90.761 (3)°	T = 100 K
V = 1389.48 (10) Å³	Plate, clear yellow
Z = 4	0.39 × 0.35 × 0.19 mm

Data collection top

Bruker APEXII Kappa CCD area detector diffractometer	3320 independent reflections
Radiation source: fine-focus sealed tube	2561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 27.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −22→22
T_min = 0.666, T_max = 0.746	k = −9→9
12270 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: mixed
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0678P)² + 0.1379P] where P = (F_o² + 2F_c²)/3
3320 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 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	0.40268 (5)	0.64764 (14)	0.01669 (8)	0.0193 (2)
N1	0.07275 (6)	0.53937 (17)	0.25056 (10)	0.0205 (3)
C1	0.38550 (7)	0.64612 (17)	0.12161 (11)	0.0145 (3)
O2	0.81017 (6)	0.60742 (15)	0.17555 (9)	0.0254 (3)
N2	0.79887 (6)	0.59843 (16)	0.28197 (10)	0.0189 (3)
C2	0.44638 (7)	0.65714 (18)	0.21487 (12)	0.0162 (3)
H2	0.432687	0.695454	0.292062	0.019*
O3	0.85104 (6)	0.57987 (16)	0.35600 (9)	0.0292 (3)
C3	0.51981 (7)	0.61451 (17)	0.19275 (12)	0.0156 (3)
H3	0.532011	0.578168	0.114587	0.019*
C4	0.30435 (7)	0.62866 (17)	0.15869 (11)	0.0141 (3)
C5	0.24711 (7)	0.59749 (18)	0.07252 (11)	0.0154 (3)
H5	0.261307	0.595641	−0.008048	0.019*
C6	0.17102 (8)	0.56948 (18)	0.10089 (12)	0.0168 (3)
H6	0.133772	0.548627	0.040059	0.020*
C7	0.14770 (7)	0.57146 (18)	0.22001 (11)	0.0155 (3)
C8	0.20495 (7)	0.60892 (18)	0.30661 (12)	0.0172 (3)
H8	0.190843	0.615961	0.387096	0.021*
C9	0.28085 (7)	0.63541 (18)	0.27630 (12)	0.0163 (3)
H9	0.318238	0.658831	0.336557	0.020*
C10	0.58321 (7)	0.61938 (17)	0.27977 (11)	0.0149 (3)
C11	0.65932 (7)	0.60289 (18)	0.24156 (11)	0.0154 (3)
H11	0.669921	0.586105	0.160316	0.018*
C12	0.71904 (7)	0.61135 (17)	0.32371 (12)	0.0159 (3)
C13	0.70704 (8)	0.62847 (18)	0.44304 (12)	0.0176 (3)
H13	0.749151	0.632712	0.497489	0.021*
C14	0.63139 (8)	0.63927 (18)	0.48083 (12)	0.0187 (3)
H14	0.621331	0.647757	0.562745	0.022*
C15	0.57042 (8)	0.63789 (18)	0.40118 (12)	0.0174 (3)
H15	0.519110	0.649624	0.428883	0.021*
C16	0.01685 (9)	0.4836 (2)	0.16067 (14)	0.0246 (3)
C17	0.05477 (8)	0.5002 (2)	0.37305 (12)	0.0235 (3)
H17A	0.083637	0.388553	0.399692	0.035*
H17B	−0.000728	0.476410	0.380111	0.035*
H17C	0.069292	0.609223	0.421831	0.035*
H16A	0.0117 (10)	0.580 (2)	0.0989 (16)	0.033 (5)*
H16B	0.0326 (10)	0.362 (2)	0.1247 (15)	0.035 (5)*
H16C	−0.0330 (12)	0.467 (3)	0.1955 (17)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0175 (5)	0.0265 (5)	0.0139 (5)	0.0000 (4)	0.0017 (4)	0.0010 (4)
N1	0.0131 (6)	0.0338 (7)	0.0144 (6)	−0.0006 (5)	0.0011 (4)	−0.0003 (5)
C1	0.0165 (7)	0.0124 (6)	0.0147 (6)	0.0013 (5)	0.0006 (5)	−0.0002 (5)
O2	0.0188 (5)	0.0376 (6)	0.0199 (5)	−0.0004 (4)	0.0024 (4)	−0.0025 (4)
N2	0.0158 (6)	0.0198 (6)	0.0210 (6)	0.0003 (4)	−0.0025 (5)	−0.0024 (5)
C2	0.0175 (7)	0.0163 (6)	0.0148 (6)	−0.0001 (5)	−0.0003 (5)	−0.0010 (5)
O3	0.0167 (5)	0.0425 (7)	0.0281 (6)	0.0048 (4)	−0.0078 (4)	−0.0017 (5)
C3	0.0174 (7)	0.0157 (6)	0.0136 (6)	−0.0008 (5)	−0.0001 (5)	0.0003 (5)
C4	0.0154 (6)	0.0121 (6)	0.0147 (7)	0.0008 (5)	−0.0005 (5)	0.0002 (5)
C5	0.0182 (6)	0.0164 (6)	0.0117 (6)	0.0021 (5)	0.0010 (5)	−0.0005 (5)
C6	0.0156 (6)	0.0202 (7)	0.0143 (6)	0.0005 (5)	−0.0037 (5)	−0.0008 (5)
C7	0.0151 (6)	0.0160 (6)	0.0154 (6)	0.0016 (5)	0.0002 (5)	0.0006 (5)
C8	0.0187 (7)	0.0220 (7)	0.0111 (6)	0.0019 (5)	0.0010 (5)	0.0001 (5)
C9	0.0168 (7)	0.0181 (7)	0.0140 (6)	0.0007 (5)	−0.0027 (5)	−0.0009 (5)
C10	0.0163 (6)	0.0127 (6)	0.0157 (7)	0.0001 (5)	−0.0006 (5)	0.0005 (5)
C11	0.0169 (7)	0.0149 (6)	0.0143 (6)	0.0006 (5)	−0.0005 (5)	−0.0003 (5)
C12	0.0152 (6)	0.0145 (6)	0.0181 (7)	0.0018 (5)	−0.0006 (5)	0.0000 (5)
C13	0.0188 (7)	0.0163 (7)	0.0176 (7)	0.0005 (5)	−0.0054 (5)	−0.0004 (5)
C14	0.0254 (7)	0.0185 (7)	0.0122 (6)	−0.0001 (5)	0.0003 (5)	−0.0007 (5)
C15	0.0164 (7)	0.0175 (7)	0.0183 (7)	0.0003 (5)	0.0017 (5)	−0.0009 (5)
C16	0.0148 (7)	0.0382 (9)	0.0207 (8)	−0.0023 (6)	−0.0002 (6)	−0.0016 (7)
C17	0.0168 (7)	0.0359 (8)	0.0181 (7)	0.0008 (6)	0.0046 (5)	0.0051 (6)

Geometric parameters (Å, º) top

O1—C1	1.2312 (15)	C8—H8	0.9500
N1—C7	1.3668 (16)	C8—C9	1.3759 (18)
N1—C16	1.4516 (18)	C9—H9	0.9500
N1—C17	1.4552 (17)	C10—C11	1.3979 (18)
C1—C2	1.4860 (18)	C10—C15	1.4045 (18)
C1—C4	1.4775 (17)	C11—H11	0.9500
O2—N2	1.2277 (15)	C11—C12	1.3845 (18)
N2—O3	1.2326 (14)	C12—C13	1.3781 (18)
N2—C12	1.4700 (17)	C13—H13	0.9500
C2—H2	0.9500	C13—C14	1.3861 (19)
C2—C3	1.3339 (18)	C14—H14	0.9500
C3—H3	0.9500	C14—C15	1.3808 (19)
C3—C10	1.4672 (18)	C15—H15	0.9500
C4—C5	1.4005 (17)	C16—H16A	0.983 (18)
C4—C9	1.4013 (18)	C16—H16B	0.989 (17)
C5—H5	0.9500	C16—H16C	0.96 (2)
C5—C6	1.3749 (18)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C6—C7	1.4161 (18)	C17—H17C	0.9800
C7—C8	1.4117 (18)

C7—N1—C16	119.57 (11)	C8—C9—H9	119.2
C7—N1—C17	119.33 (11)	C11—C10—C3	119.30 (12)
C16—N1—C17	118.06 (12)	C11—C10—C15	118.27 (12)
O1—C1—C2	120.67 (11)	C15—C10—C3	122.42 (12)
O1—C1—C4	121.28 (12)	C10—C11—H11	120.4
C4—C1—C2	118.04 (11)	C12—C11—C10	119.11 (12)
O2—N2—O3	123.44 (11)	C12—C11—H11	120.4
O2—N2—C12	118.47 (11)	C11—C12—N2	118.52 (12)
O3—N2—C12	118.09 (11)	C13—C12—N2	118.48 (12)
C1—C2—H2	119.2	C13—C12—C11	122.99 (12)
C3—C2—C1	121.55 (12)	C12—C13—H13	121.2
C3—C2—H2	119.2	C12—C13—C14	117.67 (12)
C2—C3—H3	117.5	C14—C13—H13	121.2
C2—C3—C10	125.07 (12)	C13—C14—H14	119.5
C10—C3—H3	117.5	C15—C14—C13	120.98 (13)
C5—C4—C1	118.77 (11)	C15—C14—H14	119.5
C5—C4—C9	117.30 (12)	C10—C15—H15	119.5
C9—C4—C1	123.90 (12)	C14—C15—C10	120.91 (12)
C4—C5—H5	119.0	C14—C15—H15	119.5
C6—C5—C4	122.05 (12)	N1—C16—H16A	111.4 (10)
C6—C5—H5	119.0	N1—C16—H16B	109.9 (10)
C5—C6—H6	119.7	N1—C16—H16C	109.8 (11)
C5—C6—C7	120.56 (12)	H16A—C16—H16B	109.4 (14)
C7—C6—H6	119.7	H16A—C16—H16C	107.8 (15)
N1—C7—C6	121.62 (12)	H16B—C16—H16C	108.4 (14)
N1—C7—C8	121.00 (12)	N1—C17—H17A	109.5
C8—C7—C6	117.38 (12)	N1—C17—H17B	109.5
C7—C8—H8	119.5	N1—C17—H17C	109.5
C9—C8—C7	121.06 (12)	H17A—C17—H17B	109.5
C9—C8—H8	119.5	H17A—C17—H17C	109.5
C4—C9—H9	119.2	H17B—C17—H17C	109.5
C8—C9—C4	121.59 (12)

O1—C1—C2—C3	−19.7 (2)	C4—C5—C6—C7	0.1 (2)
O1—C1—C4—C5	5.38 (18)	C5—C4—C9—C8	1.23 (19)
O1—C1—C4—C9	−176.74 (12)	C5—C6—C7—N1	−178.37 (12)
N1—C7—C8—C9	177.95 (12)	C5—C6—C7—C8	1.93 (19)
C1—C2—C3—C10	−179.22 (11)	C6—C7—C8—C9	−2.35 (19)
C1—C4—C5—C6	176.37 (12)	C7—C8—C9—C4	0.8 (2)
C1—C4—C9—C8	−176.68 (12)	C9—C4—C5—C6	−1.66 (19)
O2—N2—C12—C11	10.09 (18)	C10—C11—C12—N2	−178.54 (11)
O2—N2—C12—C13	−170.87 (11)	C10—C11—C12—C13	2.5 (2)
N2—C12—C13—C14	−179.61 (11)	C11—C10—C15—C14	−0.17 (19)
C2—C1—C4—C5	−173.15 (11)	C11—C12—C13—C14	−0.61 (19)
C2—C1—C4—C9	4.74 (18)	C12—C13—C14—C15	−1.66 (19)
C2—C3—C10—C11	−169.23 (13)	C13—C14—C15—C10	2.1 (2)
C2—C3—C10—C15	11.5 (2)	C15—C10—C11—C12	−2.01 (18)
O3—N2—C12—C11	−170.20 (12)	C16—N1—C7—C6	6.14 (19)
O3—N2—C12—C13	8.84 (18)	C16—N1—C7—C8	−174.17 (13)
C3—C10—C11—C12	178.72 (12)	C17—N1—C7—C6	166.08 (12)
C3—C10—C15—C14	179.07 (12)	C17—N1—C7—C8	−14.22 (19)
C4—C1—C2—C3	158.84 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.47	3.3124 (16)	148
C5—H5···O2ⁱ	0.95	2.67	3.3067 (17)	125
C11—H11···O1ⁱ	0.95	2.88	3.5773 (16)	131
C15—H15···O1ⁱⁱ	0.95	2.68	3.5435 (16)	152
C17—H17B···O3ⁱⁱⁱ	0.98	2.68	3.5755 (17)	152

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

3-[3-(Dimethylamino)phenyl]-1-(3-nitrophenyl)prop-2-en-1-one (Hm7m) top

Crystal data top

C₁₇H₁₆N₂O₃	F(000) = 624
M_r = 296.32	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7552 (4) Å	Cell parameters from 1681 reflections
b = 15.6998 (7) Å	θ = 2.6–24.0°
c = 12.0525 (7) Å	µ = 0.10 mm⁻¹
β = 100.668 (3)°	T = 200 K
V = 1442.09 (13) Å³	Block, clear orange
Z = 4	0.39 × 0.33 × 0.25 mm

Data collection top

Bruker APEXII Kappa CCD area detector diffractometer	3056 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
φ and ω scans	θ_max = 26.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −7→9
T_min = 0.629, T_max = 0.746	k = −19→19
11497 measured reflections	l = −15→13

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0622P)² + 0.0748P] where P = (F_o² + 2F_c²)/3
3056 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 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
C1	0.3894 (3)	0.47781 (12)	0.36738 (19)	0.0361 (5)
N1	0.7377 (2)	0.69758 (11)	0.21902 (15)	0.0364 (4)
O1	0.2877 (2)	0.53451 (9)	0.38190 (16)	0.0554 (5)
C2	0.3564 (3)	0.38878 (12)	0.39197 (18)	0.0356 (5)
H2	0.427006	0.345535	0.367975	0.043*
N2	−0.1631 (2)	0.18000 (10)	0.60898 (17)	0.0411 (5)
O2	0.62970 (19)	0.74937 (9)	0.23772 (14)	0.0445 (4)
C3	0.2296 (3)	0.36699 (12)	0.44729 (18)	0.0343 (5)
H3	0.162525	0.412295	0.469835	0.041*
O3	0.8619 (2)	0.71586 (10)	0.17312 (14)	0.0518 (5)
C4	0.5534 (3)	0.50134 (12)	0.32408 (18)	0.0316 (5)
C5	0.5701 (3)	0.58465 (12)	0.28981 (17)	0.0315 (5)
H5	0.478821	0.624712	0.291478	0.038*
C6	0.7212 (3)	0.60857 (12)	0.25325 (18)	0.0320 (5)
C7	0.8569 (3)	0.55285 (13)	0.24965 (19)	0.0388 (6)
H7	0.960216	0.571074	0.224810	0.047*
C8	0.8390 (3)	0.47026 (13)	0.2829 (2)	0.0431 (6)
H8	0.930866	0.430648	0.280479	0.052*
C9	0.6885 (3)	0.44375 (13)	0.32009 (19)	0.0386 (5)
H9	0.677876	0.386332	0.342771	0.046*
C10	0.1823 (3)	0.28126 (12)	0.47704 (18)	0.0311 (5)
C11	0.0358 (2)	0.27097 (12)	0.52753 (17)	0.0315 (5)
H11	−0.028145	0.319845	0.542776	0.038*
C12	−0.0194 (3)	0.19012 (12)	0.55642 (18)	0.0326 (5)
C13	0.0783 (3)	0.12007 (13)	0.5326 (2)	0.0406 (6)
H13	0.044151	0.064351	0.550403	0.049*
C14	0.2239 (3)	0.13081 (13)	0.4835 (2)	0.0441 (6)
H14	0.289136	0.082183	0.468976	0.053*
C15	0.2770 (3)	0.21003 (13)	0.4552 (2)	0.0395 (6)
H15	0.377263	0.216077	0.421012	0.047*
C16	−0.2649 (3)	0.25448 (14)	0.6266 (2)	0.0482 (6)
H16A	−0.187783	0.297063	0.669840	0.072*
H16B	−0.356654	0.238239	0.668615	0.072*
H16C	−0.319124	0.278526	0.553447	0.072*
C17	−0.2612 (3)	0.10108 (14)	0.5915 (2)	0.0464 (6)
H17A	−0.304660	0.092786	0.510518	0.070*
H17B	−0.360675	0.103638	0.631031	0.070*
H17C	−0.184628	0.053444	0.620960	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0362 (12)	0.0342 (12)	0.0402 (14)	−0.0013 (9)	0.0131 (11)	−0.0013 (9)
N1	0.0346 (10)	0.0413 (10)	0.0350 (12)	−0.0075 (8)	0.0110 (9)	0.0033 (8)
O1	0.0486 (10)	0.0365 (9)	0.0918 (15)	0.0039 (7)	0.0405 (10)	0.0111 (8)
C2	0.0374 (12)	0.0329 (11)	0.0389 (14)	−0.0031 (9)	0.0133 (11)	−0.0015 (9)
N2	0.0430 (11)	0.0332 (10)	0.0531 (13)	−0.0082 (8)	0.0248 (10)	−0.0013 (9)
O2	0.0434 (9)	0.0373 (9)	0.0564 (12)	0.0024 (7)	0.0188 (8)	0.0063 (7)
C3	0.0348 (11)	0.0319 (11)	0.0382 (14)	−0.0029 (8)	0.0115 (10)	−0.0020 (9)
O3	0.0476 (10)	0.0526 (10)	0.0637 (13)	−0.0116 (7)	0.0324 (9)	0.0073 (8)
C4	0.0325 (11)	0.0301 (11)	0.0340 (13)	−0.0026 (8)	0.0111 (10)	−0.0020 (9)
C5	0.0298 (11)	0.0327 (11)	0.0338 (13)	−0.0015 (8)	0.0108 (10)	−0.0014 (9)
C6	0.0330 (11)	0.0335 (11)	0.0310 (12)	−0.0053 (9)	0.0096 (10)	−0.0002 (9)
C7	0.0328 (11)	0.0441 (13)	0.0434 (15)	−0.0037 (9)	0.0175 (11)	−0.0006 (10)
C8	0.0353 (12)	0.0400 (13)	0.0578 (17)	0.0046 (9)	0.0189 (12)	−0.0017 (11)
C9	0.0411 (12)	0.0322 (12)	0.0455 (15)	0.0002 (9)	0.0159 (11)	0.0003 (10)
C10	0.0306 (10)	0.0314 (11)	0.0322 (13)	−0.0052 (8)	0.0077 (10)	−0.0016 (9)
C11	0.0319 (11)	0.0306 (11)	0.0330 (13)	0.0008 (8)	0.0090 (10)	−0.0029 (9)
C12	0.0351 (11)	0.0329 (11)	0.0308 (13)	−0.0049 (9)	0.0084 (10)	−0.0017 (9)
C13	0.0452 (13)	0.0274 (11)	0.0513 (16)	−0.0060 (9)	0.0145 (12)	−0.0011 (10)
C14	0.0441 (13)	0.0310 (11)	0.0615 (17)	0.0015 (9)	0.0211 (13)	−0.0060 (11)
C15	0.0371 (12)	0.0376 (12)	0.0481 (15)	−0.0031 (9)	0.0191 (11)	−0.0037 (10)
C16	0.0449 (13)	0.0449 (14)	0.0622 (18)	−0.0052 (10)	0.0292 (13)	−0.0033 (11)
C17	0.0441 (13)	0.0441 (13)	0.0537 (17)	−0.0120 (10)	0.0160 (12)	0.0068 (11)

Geometric parameters (Å, º) top

C1—O1	1.223 (2)	C8—H8	0.9500
C1—C2	1.461 (3)	C8—C9	1.389 (3)
C1—C4	1.507 (3)	C9—H9	0.9500
N1—O2	1.218 (2)	C10—C11	1.394 (2)
N1—O3	1.2303 (19)	C10—C15	1.389 (3)
N1—C6	1.469 (3)	C11—H11	0.9500
C2—H2	0.9500	C11—C12	1.404 (3)
C2—C3	1.331 (3)	C12—C13	1.395 (3)
N2—C12	1.389 (2)	C13—H13	0.9500
N2—C16	1.448 (3)	C13—C14	1.378 (3)
N2—C17	1.449 (3)	C14—H14	0.9500
C3—H3	0.9500	C14—C15	1.373 (3)
C3—C10	1.457 (3)	C15—H15	0.9500
C4—C5	1.385 (3)	C16—H16A	0.9800
C4—C9	1.392 (3)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C5—C6	1.378 (2)	C17—H17A	0.9800
C6—C7	1.376 (3)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C7—C8	1.372 (3)

O1—C1—C2	121.68 (18)	C8—C9—H9	120.0
O1—C1—C4	118.63 (18)	C11—C10—C3	118.49 (16)
C2—C1—C4	119.69 (17)	C15—C10—C3	122.07 (17)
O2—N1—O3	123.37 (17)	C15—C10—C11	119.43 (17)
O2—N1—C6	118.95 (15)	C10—C11—H11	119.2
O3—N1—C6	117.68 (16)	C10—C11—C12	121.59 (17)
C1—C2—H2	119.3	C12—C11—H11	119.2
C3—C2—C1	121.38 (18)	N2—C12—C11	121.59 (17)
C3—C2—H2	119.3	N2—C12—C13	121.05 (17)
C12—N2—C16	118.67 (16)	C13—C12—C11	117.34 (18)
C12—N2—C17	118.37 (16)	C12—C13—H13	119.6
C16—N2—C17	115.23 (17)	C14—C13—C12	120.73 (18)
C2—C3—H3	116.4	C14—C13—H13	119.6
C2—C3—C10	127.12 (18)	C13—C14—H14	119.2
C10—C3—H3	116.4	C15—C14—C13	121.64 (18)
C5—C4—C1	117.81 (16)	C15—C14—H14	119.2
C5—C4—C9	119.36 (17)	C10—C15—H15	120.4
C9—C4—C1	122.81 (18)	C14—C15—C10	119.26 (18)
C4—C5—H5	120.5	C14—C15—H15	120.4
C6—C5—C4	119.01 (17)	N2—C16—H16A	109.5
C6—C5—H5	120.5	N2—C16—H16B	109.5
C5—C6—N1	118.21 (17)	N2—C16—H16C	109.5
C7—C6—N1	119.26 (17)	H16A—C16—H16B	109.5
C7—C6—C5	122.52 (19)	H16A—C16—H16C	109.5
C6—C7—H7	120.9	H16B—C16—H16C	109.5
C8—C7—C6	118.21 (17)	N2—C17—H17A	109.5
C8—C7—H7	120.9	N2—C17—H17B	109.5
C7—C8—H8	119.5	N2—C17—H17C	109.5
C7—C8—C9	120.91 (18)	H17A—C17—H17B	109.5
C9—C8—H8	119.5	H17A—C17—H17C	109.5
C4—C9—H9	120.0	H17B—C17—H17C	109.5
C8—C9—C4	119.98 (19)

C1—C2—C3—C10	179.8 (2)	C4—C5—C6—N1	−179.00 (19)
C1—C4—C5—C6	177.95 (19)	C4—C5—C6—C7	−0.2 (3)
C1—C4—C9—C8	−177.7 (2)	C5—C4—C9—C8	0.6 (3)
N1—C6—C7—C8	179.5 (2)	C5—C6—C7—C8	0.6 (3)
O1—C1—C2—C3	−10.6 (4)	C6—C7—C8—C9	−0.5 (4)
O1—C1—C4—C5	−7.7 (3)	C7—C8—C9—C4	−0.1 (4)
O1—C1—C4—C9	170.6 (2)	C9—C4—C5—C6	−0.4 (3)
C2—C1—C4—C5	172.9 (2)	C10—C11—C12—N2	178.6 (2)
C2—C1—C4—C9	−8.8 (3)	C10—C11—C12—C13	0.0 (3)
C2—C3—C10—C11	−175.0 (2)	C11—C10—C15—C14	0.2 (3)
C2—C3—C10—C15	4.1 (4)	C11—C12—C13—C14	0.5 (3)
N2—C12—C13—C14	−178.0 (2)	C12—C13—C14—C15	−0.8 (4)
O2—N1—C6—C5	9.5 (3)	C13—C14—C15—C10	0.4 (4)
O2—N1—C6—C7	−169.4 (2)	C15—C10—C11—C12	−0.4 (3)
C3—C10—C11—C12	178.7 (2)	C16—N2—C12—C11	4.5 (3)
C3—C10—C15—C14	−178.9 (2)	C16—N2—C12—C13	−177.0 (2)
O3—N1—C6—C5	−170.91 (19)	C17—N2—C12—C11	152.4 (2)
O3—N1—C6—C7	10.2 (3)	C17—N2—C12—C13	−29.1 (3)
C4—C1—C2—C3	168.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ⁱ	0.95	2.50	3.442 (2)	174
C16—H16B···O2ⁱⁱ	0.98	2.58	3.520 (2)	160

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

1-(3-Nitrophenyl)-3-phenylprop-2-en-1-one (Hm1-) top

Crystal data top

C₁₅H₁₁NO₃	F(000) = 1056
M_r = 253.25	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7856 (8) Å	Cell parameters from 2603 reflections
b = 15.9841 (9) Å	θ = 2.4–24.0°
c = 10.3188 (6) Å	µ = 0.10 mm⁻¹
β = 99.210 (4)°	T = 100 K
V = 2407.3 (2) Å³	Block, clear colourless
Z = 8	0.61 × 0.35 × 0.25 mm

Data collection top

Bruker APEXII Kappa CCD area detector diffractometer	4408 independent reflections
Radiation source: fine-focus sealed tube	2657 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
φ and ω scans	θ_max = 25.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −17→17
T_min = 0.610, T_max = 0.746	k = −18→19
25080 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0721P)²] where P = (F_o² + 2F_c²)/3
4408 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.24 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
O1	0.15404 (12)	0.16690 (10)	0.61388 (17)	0.0359 (5)
O2	0.01454 (14)	0.38743 (11)	0.34410 (18)	0.0473 (6)
O3	−0.05654 (12)	0.36438 (11)	0.14763 (17)	0.0383 (5)
N1	−0.01292 (15)	0.34002 (13)	0.2521 (2)	0.0323 (5)
C1	0.12448 (16)	0.11250 (15)	0.5350 (2)	0.0254 (6)
C2	0.14090 (16)	0.02299 (14)	0.5655 (2)	0.0255 (6)
H2	0.112881	−0.018632	0.506696	0.031*
C3	0.19525 (16)	0.00085 (14)	0.6761 (2)	0.0253 (6)
H3	0.220584	0.045244	0.731502	0.030*
C4	0.07058 (15)	0.13797 (14)	0.4054 (2)	0.0231 (6)
C5	0.05461 (16)	0.22346 (14)	0.3858 (2)	0.0248 (6)
H5	0.077179	0.262547	0.452566	0.030*
C6	0.00593 (16)	0.25020 (14)	0.2690 (2)	0.0252 (6)
C7	−0.02844 (17)	0.19594 (15)	0.1684 (2)	0.0279 (6)
H7	−0.062116	0.216229	0.088457	0.033*
C8	−0.01236 (16)	0.11190 (15)	0.1879 (2)	0.0271 (6)
H8	−0.034651	0.073409	0.120088	0.032*
C9	0.03611 (16)	0.08256 (15)	0.3055 (2)	0.0258 (6)
H9	0.045864	0.024162	0.317841	0.031*
C10	0.22033 (16)	−0.08377 (14)	0.7218 (2)	0.0238 (6)
C11	0.26673 (16)	−0.09467 (15)	0.8493 (2)	0.0266 (6)
H11	0.282266	−0.047021	0.903293	0.032*
C12	0.29063 (17)	−0.17356 (15)	0.8988 (2)	0.0301 (6)
H12	0.321996	−0.179789	0.986089	0.036*
C13	0.26862 (17)	−0.24322 (16)	0.8206 (3)	0.0325 (6)
H13	0.284275	−0.297540	0.854305	0.039*
C14	0.22364 (17)	−0.23354 (15)	0.6929 (3)	0.0302 (6)
H14	0.209076	−0.281420	0.639024	0.036*
C15	0.19979 (17)	−0.15487 (15)	0.6432 (2)	0.0282 (6)
H15	0.169329	−0.148993	0.555349	0.034*
O4	0.35937 (12)	0.39992 (10)	0.37652 (16)	0.0314 (4)
O5	0.44124 (12)	0.62138 (10)	0.68540 (17)	0.0357 (5)
O6	0.52132 (14)	0.59755 (11)	0.87609 (17)	0.0447 (5)
N2	0.48438 (15)	0.57425 (13)	0.7669 (2)	0.0317 (5)
C16	0.38593 (16)	0.34642 (15)	0.4587 (2)	0.0261 (6)
C17	0.36217 (17)	0.25751 (15)	0.4363 (2)	0.0273 (6)
H17	0.385793	0.216860	0.499959	0.033*
C18	0.30757 (16)	0.23402 (15)	0.3268 (2)	0.0254 (6)
H18	0.285045	0.277608	0.267756	0.031*
C19	0.44235 (15)	0.37308 (14)	0.5864 (2)	0.0231 (5)
C20	0.44373 (15)	0.45800 (14)	0.6154 (2)	0.0236 (6)
H20	0.413123	0.496873	0.553799	0.028*
C21	0.48994 (17)	0.48510 (15)	0.7343 (2)	0.0262 (6)
C22	0.53737 (16)	0.43117 (16)	0.8256 (2)	0.0294 (6)
H22	0.568880	0.451388	0.907075	0.035*
C23	0.53761 (16)	0.34715 (16)	0.7950 (2)	0.0283 (6)
H23	0.570586	0.309004	0.855604	0.034*
C24	0.49037 (16)	0.31779 (15)	0.6772 (2)	0.0266 (6)
H24	0.490620	0.259682	0.657880	0.032*
C25	0.27816 (15)	0.14936 (15)	0.2866 (2)	0.0243 (6)
C30	0.29847 (16)	0.07941 (15)	0.3671 (3)	0.0286 (6)
H30	0.331611	0.086022	0.453284	0.034*
C29	0.27051 (17)	0.00044 (15)	0.3220 (3)	0.0323 (6)
H29	0.284069	−0.046713	0.377719	0.039*
C28	0.22299 (18)	−0.01024 (16)	0.1962 (3)	0.0357 (7)
H28	0.204939	−0.064705	0.165510	0.043*
C27	0.20172 (17)	0.05826 (16)	0.1152 (3)	0.0329 (6)
H27	0.168703	0.051101	0.029069	0.039*
C26	0.22886 (16)	0.13736 (15)	0.1605 (2)	0.0270 (6)
H26	0.213718	0.184348	0.104843	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0504 (12)	0.0234 (10)	0.0272 (10)	0.0002 (8)	−0.0146 (9)	−0.0021 (8)
O2	0.0765 (15)	0.0291 (11)	0.0296 (11)	0.0078 (10)	−0.0120 (10)	−0.0019 (9)
O3	0.0471 (12)	0.0345 (11)	0.0276 (11)	0.0066 (9)	−0.0113 (9)	0.0096 (8)
N1	0.0386 (13)	0.0309 (12)	0.0249 (13)	0.0054 (10)	−0.0025 (11)	0.0036 (10)
C1	0.0241 (13)	0.0262 (13)	0.0239 (14)	−0.0004 (10)	−0.0020 (11)	0.0002 (11)
C2	0.0295 (14)	0.0218 (13)	0.0237 (14)	−0.0008 (10)	−0.0008 (11)	−0.0023 (10)
C3	0.0298 (14)	0.0219 (13)	0.0230 (14)	−0.0028 (10)	0.0008 (11)	−0.0005 (10)
C4	0.0228 (13)	0.0245 (13)	0.0213 (13)	−0.0006 (10)	0.0011 (11)	0.0032 (11)
C5	0.0289 (14)	0.0236 (14)	0.0207 (13)	−0.0008 (10)	0.0005 (11)	0.0001 (10)
C6	0.0301 (14)	0.0241 (13)	0.0205 (13)	0.0053 (11)	0.0015 (11)	0.0022 (11)
C7	0.0290 (14)	0.0349 (15)	0.0185 (13)	0.0012 (11)	0.0001 (11)	0.0041 (11)
C8	0.0290 (14)	0.0294 (14)	0.0215 (14)	−0.0017 (11)	0.0003 (11)	−0.0023 (11)
C9	0.0275 (13)	0.0259 (14)	0.0230 (14)	0.0001 (10)	0.0010 (11)	0.0013 (11)
C10	0.0245 (13)	0.0245 (13)	0.0213 (13)	−0.0012 (10)	0.0003 (11)	0.0017 (10)
C11	0.0291 (14)	0.0261 (13)	0.0233 (14)	−0.0003 (11)	0.0007 (11)	0.0007 (11)
C12	0.0287 (14)	0.0348 (15)	0.0248 (14)	0.0021 (11)	−0.0024 (12)	0.0061 (12)
C13	0.0365 (15)	0.0248 (14)	0.0358 (16)	0.0039 (11)	0.0047 (13)	0.0062 (12)
C14	0.0348 (15)	0.0255 (14)	0.0299 (15)	−0.0010 (11)	0.0042 (12)	−0.0016 (11)
C15	0.0324 (14)	0.0275 (14)	0.0236 (14)	−0.0006 (11)	0.0015 (12)	0.0021 (11)
O4	0.0389 (10)	0.0259 (9)	0.0255 (10)	−0.0009 (8)	−0.0074 (8)	0.0028 (8)
O5	0.0439 (11)	0.0262 (10)	0.0331 (11)	0.0037 (8)	−0.0057 (9)	−0.0007 (8)
O6	0.0665 (14)	0.0374 (11)	0.0248 (11)	−0.0098 (10)	−0.0090 (10)	−0.0076 (9)
N2	0.0390 (13)	0.0318 (12)	0.0227 (13)	−0.0049 (10)	0.0002 (11)	−0.0043 (10)
C16	0.0252 (13)	0.0274 (14)	0.0256 (14)	0.0022 (11)	0.0034 (11)	−0.0016 (11)
C17	0.0335 (14)	0.0224 (13)	0.0243 (14)	0.0002 (11)	−0.0003 (12)	0.0021 (11)
C18	0.0275 (14)	0.0247 (13)	0.0234 (14)	0.0020 (10)	0.0016 (11)	0.0009 (10)
C19	0.0245 (13)	0.0246 (14)	0.0199 (13)	−0.0026 (10)	0.0027 (11)	0.0005 (10)
C20	0.0258 (13)	0.0236 (13)	0.0207 (13)	−0.0022 (10)	0.0014 (11)	0.0014 (10)
C21	0.0294 (14)	0.0252 (13)	0.0241 (14)	−0.0010 (11)	0.0044 (11)	−0.0006 (11)
C22	0.0296 (14)	0.0366 (15)	0.0206 (14)	−0.0043 (11)	−0.0002 (11)	−0.0002 (11)
C23	0.0249 (13)	0.0316 (15)	0.0269 (15)	0.0014 (11)	−0.0009 (11)	0.0070 (11)
C24	0.0291 (14)	0.0258 (14)	0.0238 (14)	−0.0005 (10)	0.0007 (11)	0.0008 (11)
C25	0.0195 (12)	0.0272 (14)	0.0262 (14)	0.0006 (10)	0.0036 (11)	−0.0035 (11)
C30	0.0272 (13)	0.0274 (14)	0.0300 (15)	0.0014 (11)	0.0004 (11)	−0.0005 (11)
C29	0.0334 (15)	0.0239 (14)	0.0399 (17)	−0.0009 (11)	0.0071 (13)	−0.0014 (12)
C28	0.0363 (16)	0.0263 (15)	0.0450 (18)	−0.0023 (12)	0.0079 (14)	−0.0093 (13)
C27	0.0278 (14)	0.0366 (16)	0.0333 (16)	−0.0029 (11)	0.0022 (12)	−0.0095 (12)
C26	0.0270 (13)	0.0271 (14)	0.0266 (14)	0.0006 (11)	0.0034 (11)	−0.0018 (11)

Geometric parameters (Å, º) top

O1—C1	1.223 (3)	O4—C16	1.224 (3)
O2—N1	1.232 (3)	O5—N2	1.229 (3)
O3—N1	1.227 (2)	O6—N2	1.229 (3)
N1—C6	1.468 (3)	N2—C21	1.469 (3)
C1—C2	1.477 (3)	C16—C17	1.473 (3)
C1—C4	1.499 (3)	C16—C19	1.504 (3)
C2—H2	0.9500	C17—H17	0.9500
C2—C3	1.334 (3)	C17—C18	1.333 (3)
C3—H3	0.9500	C18—H18	0.9500
C3—C10	1.460 (3)	C18—C25	1.461 (3)
C4—C5	1.396 (3)	C19—C20	1.389 (3)
C4—C9	1.393 (3)	C19—C24	1.396 (3)
C5—H5	0.9500	C20—H20	0.9500
C5—C6	1.370 (3)	C20—C21	1.375 (3)
C6—C7	1.385 (3)	C21—C22	1.383 (3)
C7—H7	0.9500	C22—H22	0.9500
C7—C8	1.373 (3)	C22—C23	1.380 (3)
C8—H8	0.9500	C23—H23	0.9500
C8—C9	1.388 (3)	C23—C24	1.384 (3)
C9—H9	0.9500	C24—H24	0.9500
C10—C11	1.394 (3)	C25—C30	1.397 (3)
C10—C15	1.401 (3)	C25—C26	1.399 (3)
C11—H11	0.9500	C30—H30	0.9500
C11—C12	1.385 (3)	C30—C29	1.386 (3)
C12—H12	0.9500	C29—H29	0.9500
C12—C13	1.383 (4)	C29—C28	1.384 (4)
C13—H13	0.9500	C28—H28	0.9500
C13—C14	1.387 (4)	C28—C27	1.383 (4)
C14—H14	0.9500	C27—H27	0.9500
C14—C15	1.382 (3)	C27—C26	1.385 (3)
C15—H15	0.9500	C26—H26	0.9500

O2—N1—C6	118.5 (2)	O5—N2—O6	123.2 (2)
O3—N1—O2	122.9 (2)	O5—N2—C21	118.7 (2)
O3—N1—C6	118.5 (2)	O6—N2—C21	118.1 (2)
O1—C1—C2	121.2 (2)	O4—C16—C17	121.5 (2)
O1—C1—C4	118.9 (2)	O4—C16—C19	118.7 (2)
C2—C1—C4	119.9 (2)	C17—C16—C19	119.7 (2)
C1—C2—H2	120.1	C16—C17—H17	119.9
C3—C2—C1	119.7 (2)	C18—C17—C16	120.1 (2)
C3—C2—H2	120.1	C18—C17—H17	119.9
C2—C3—H3	116.2	C17—C18—H18	116.1
C2—C3—C10	127.5 (2)	C17—C18—C25	127.9 (2)
C10—C3—H3	116.2	C25—C18—H18	116.1
C5—C4—C1	116.7 (2)	C20—C19—C16	116.9 (2)
C9—C4—C1	124.5 (2)	C20—C19—C24	119.1 (2)
C9—C4—C5	118.8 (2)	C24—C19—C16	124.0 (2)
C4—C5—H5	120.5	C19—C20—H20	120.4
C6—C5—C4	119.1 (2)	C21—C20—C19	119.2 (2)
C6—C5—H5	120.5	C21—C20—H20	120.4
C5—C6—N1	118.2 (2)	C20—C21—N2	118.1 (2)
C5—C6—C7	122.8 (2)	C20—C21—C22	122.5 (2)
C7—C6—N1	118.9 (2)	C22—C21—N2	119.3 (2)
C6—C7—H7	121.0	C21—C22—H22	121.0
C8—C7—C6	118.0 (2)	C23—C22—C21	118.1 (2)
C8—C7—H7	121.0	C23—C22—H22	121.0
C7—C8—H8	119.6	C22—C23—H23	119.6
C7—C8—C9	120.7 (2)	C22—C23—C24	120.8 (2)
C9—C8—H8	119.6	C24—C23—H23	119.6
C4—C9—H9	119.7	C19—C24—H24	119.8
C8—C9—C4	120.6 (2)	C23—C24—C19	120.4 (2)
C8—C9—H9	119.7	C23—C24—H24	119.8
C11—C10—C3	118.8 (2)	C30—C25—C18	123.1 (2)
C11—C10—C15	118.2 (2)	C30—C25—C26	118.3 (2)
C15—C10—C3	123.0 (2)	C26—C25—C18	118.6 (2)
C10—C11—H11	119.3	C25—C30—H30	119.8
C12—C11—C10	121.3 (2)	C29—C30—C25	120.3 (2)
C12—C11—H11	119.3	C29—C30—H30	119.8
C11—C12—H12	120.2	C30—C29—H29	119.8
C13—C12—C11	119.7 (2)	C28—C29—C30	120.5 (2)
C13—C12—H12	120.2	C28—C29—H29	119.8
C12—C13—H13	120.1	C29—C28—H28	120.0
C12—C13—C14	119.8 (2)	C27—C28—C29	120.1 (2)
C14—C13—H13	120.1	C27—C28—H28	120.0
C13—C14—H14	119.7	C28—C27—H27	120.2
C15—C14—C13	120.6 (2)	C28—C27—C26	119.6 (2)
C15—C14—H14	119.7	C26—C27—H27	120.2
C10—C15—H15	119.8	C25—C26—H26	119.4
C14—C15—C10	120.3 (2)	C27—C26—C25	121.2 (2)
C14—C15—H15	119.8	C27—C26—H26	119.4

O1—C1—C2—C3	−5.7 (4)	O4—C16—C17—C18	−2.7 (4)
O1—C1—C4—C5	−2.5 (3)	O4—C16—C19—C20	14.0 (3)
O1—C1—C4—C9	177.5 (2)	O4—C16—C19—C24	−167.8 (2)
O2—N1—C6—C5	−1.1 (3)	O5—N2—C21—C20	−2.2 (3)
O2—N1—C6—C7	176.9 (2)	O5—N2—C21—C22	−179.3 (2)
O3—N1—C6—C5	−180.0 (2)	O6—N2—C21—C20	175.9 (2)
O3—N1—C6—C7	−2.0 (3)	O6—N2—C21—C22	−1.1 (3)
N1—C6—C7—C8	−178.0 (2)	N2—C21—C22—C23	176.8 (2)
C1—C2—C3—C10	−179.1 (2)	C16—C17—C18—C25	178.7 (2)
C1—C4—C5—C6	179.8 (2)	C16—C19—C20—C21	176.3 (2)
C1—C4—C9—C8	−179.3 (2)	C16—C19—C24—C23	−177.3 (2)
C2—C1—C4—C5	177.4 (2)	C17—C16—C19—C20	−164.6 (2)
C2—C1—C4—C9	−2.6 (4)	C17—C16—C19—C24	13.6 (4)
C2—C3—C10—C11	−170.3 (2)	C17—C18—C25—C30	5.8 (4)
C2—C3—C10—C15	9.6 (4)	C17—C18—C25—C26	−172.9 (2)
C3—C10—C11—C12	178.7 (2)	C18—C25—C30—C29	−178.4 (2)
C3—C10—C15—C14	−178.6 (2)	C18—C25—C26—C27	177.9 (2)
C4—C1—C2—C3	174.4 (2)	C19—C16—C17—C18	175.9 (2)
C4—C5—C6—N1	177.9 (2)	C19—C20—C21—N2	−175.3 (2)
C4—C5—C6—C7	0.0 (4)	C19—C20—C21—C22	1.7 (4)
C5—C4—C9—C8	0.7 (4)	C20—C19—C24—C23	0.9 (4)
C5—C6—C7—C8	−0.2 (4)	C20—C21—C22—C23	−0.1 (4)
C6—C7—C8—C9	0.7 (4)	C21—C22—C23—C24	−1.1 (4)
C7—C8—C9—C4	−0.9 (4)	C22—C23—C24—C19	0.7 (4)
C9—C4—C5—C6	−0.2 (4)	C24—C19—C20—C21	−2.0 (3)
C10—C11—C12—C13	0.3 (4)	C25—C30—C29—C28	0.6 (4)
C11—C10—C15—C14	1.3 (4)	C30—C25—C26—C27	−0.9 (4)
C11—C12—C13—C14	0.6 (4)	C30—C29—C28—C27	−1.0 (4)
C12—C13—C14—C15	−0.6 (4)	C29—C28—C27—C26	0.5 (4)
C13—C14—C15—C10	−0.4 (4)	C28—C27—C26—C25	0.5 (4)
C15—C10—C11—C12	−1.2 (4)	C26—C25—C30—C29	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.95	2.51	3.456 (3)	174
C3—H3···O4ⁱⁱ	0.95	2.50	3.328 (3)	146
C9—H9···O3ⁱ	0.95	2.58	3.527 (3)	175
C15—H15···O3ⁱ	0.95	2.47	3.399 (3)	166
C17—H17···O6ⁱⁱⁱ	0.95	2.57	3.491 (3)	164
C18—H18···O1^iv	0.95	2.46	3.300 (3)	147
C30—H30···O6ⁱⁱⁱ	0.95	2.58	3.456 (3)	154
C26—H26···O1^iv	0.95	2.54	3.328 (3)	140

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

Torsion and ring angles (°) describing the planarity of molecules in each crystal structure top

	Gm8p	Hm7m	Hm1- (1)	Hm1- (2)
Φ₁	-173.15 (11)	172.9 (2)	177.4 (2)	-164.6 (2)
Φ₂	158.84 (12)	168.8 (2)	174.4 (2)	175.9 (2)
Φ₃	-169.23 (13)	-175.0 (2)	-170.3 (3)	-172.9 (9)
Ring twist angle	3.61 (4)	13.8 (8)	1.88 (8)	12.58 (8)
Ring fold angle	11.46 (4)	0.59 (8)	2.58 (8)	6.66 (8)

Acknowledgements

The GU co-authors thank J. Hazen, S. Economu and B. Hendricks for their assistance, as well as the Howard Hughes Medical Institute for supporting equipment acquisition through its Undergraduate Science Education Program.

Funding information

Funding for this research was provided by: EPSRC (grant No. EP/L015544/1 to C. L. Hall; grant No. EP/L016648/1 to V. Hamilton); European Union's Horizon 2020 Research and Innovation Programme (grant No. 736899).

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Volume 76| Part 10| October 2020| Pages 1599-1604

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

Crystal structures of three functionalized chalcones: 4′-di­methyl­amino-3-nitro­chalcone, 3-di­methyl­amino-3′-nitrochalcone and 3′-nitro­chalcone

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Crystal structures of three functionalized chalcones: 4′-dimethylamino-3-nitrochalcone, 3-dimethylamino-3′-nitrochalcone and 3′-nitrochalcone

3. Supramolecular features