Crystal structures of 3-chloro-2-nitro­benzoic acid with quinoline derivatives: 3-chloro-2-nitro­benzoic acid–5-nitro­quinoline (1/1), 3-chloro-2-nitro­benzoic acid–6-nitro­quinoline (1/1) and 8-hy­droxy­quinolinium 3-chloro-2-nitro­benzoate

Gotoh, K.; Ishida, H.

doi:10.1107/S2056989019012799

research communications

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ISSN: 2056-9890

Volume 75| Part 10| October 2019| Pages 1552-1557

https://doi.org/10.1107/S2056989019012799

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Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives: 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid–6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate

Kazuma Gotoh ^a and Hiroyuki Ishida ^a ^*

^aDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
^*Correspondence e-mail: ishidah@cc.okayama-u.ac.jp

Edited by A. J. Lough, University of Toronto, Canada (Received 10 September 2019; accepted 14 September 2019; online 27 September 2019)

The structures of three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190 K. In each of the two isomeric compounds, (I) and (II), C₇H₄ClNO₄·C₉H₆N₂O₂, the acid and base molecules are held together by O—H⋯N and C—H⋯O hydrogen bonds. In compound (III), C₉H₈NO⁺·C₇H₃ClNO₄⁻, an acid–base interaction involving H-atom transfer occurs and the H atom is located at the N site of the base molecule. In the crystal of (I), the hydrogen-bonded acid–base units are linked by C—H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C—H⋯O hydrogen bond, forming wide ribbons parallel to the ( $[\overline{1}]$ 03) plane. These ribbons are stacked via π–π interactions between the quinoline ring systems [centroid–centroid distances = 3.4935 (5)–3.7721 (6) Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid–base units are also linked into a tape structure along the b-axis direction via C—H⋯O hydrogen bonds. Inversion-related tapes are linked by further C—H⋯O hydrogen bonds to form wide ribbons parallel to the ( $[\overline{3}]$ 08) plane. The ribbons are linked by weak π–π interactions [centroid–centroid distances = 3.8016 (8)–3.9247 (9) Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N—H⋯O and O—H⋯O hydrogen bonds, forming a 2₁ helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π–π interactions [centroid–centroid distances = 3.8016 (8)–3.9247 (9) Å], and the molecular chains are linked into layers parallel to the ab plane through these interactions.

Keywords: crystal structure; 3-chloro-2-nitrobonzoic acid; 5-nitroquinoline; 6-nitroquinoline; 8-hydroxyqunoline; hydrogen bond.

CCDC references: 1953605; 1953604; 1953603

1. Chemical context

The hydrogen bonds formed between organic acids and organic bases vary from an O—H⋯N type to an O⁻⋯H—N⁺ type depending on the pK_a values of the acids and bases as well as intermolecular interactions in the crystals, and at an appropriate ΔpK_a [pKa(base) − pKa(acid)] value, a short strong hydrogen bond with a broad single minimum potential energy curve for the H atom or a double-minimum potential is observed (Schmidtmann & Wilson, 2008 ; Gilli & Gilli, 2009 ). For the system of quinoline–chloro- and nitro-substituted benzoic acids, we have shown that three compounds of quinoline with 3-chloro-2-nitrobenzoic acid, 4-chloro-2-nitrobenzoic acid and 5-chloro-2-nitrobenzoic acid, the ΔpK_a values of which are 3.08, 2.93 and 3.04, respectively, have a short double-well O⋯H⋯N hydrogen bond between the carboxy O atom and the aromatic N atom (Gotoh & Ishida, 2009 ). Similar O⋯H⋯N hydrogen bonds have been also observed in compounds of phthalazine with 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid with ΔpK_a values of 1.65 and 1.50, respectively (Gotoh & Ishida, 2011 ), and of isoquinoline with 3-chloro-2-nitrobenzoic acid with ΔpK_a = 3.58 (Gotoh & Ishida, 2015 ).

We report here the crystal structures of the title compounds in order to extend our studies of short hydrogen bonding in pyridine derivative–chloro- and nitro-substituted benzoic acid systems. The ΔpK_a values are 0.98 and 1.42 and 3.02 for 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), (I), 3-chloro-2-nitrobenzoic acid–6-nitroquinoline (1/1), (II), and 8-hydroxyquinolium 3-chloro-2-nitrobenzoate, (III), respectively.

2. Structural commentary

The molecular structure of (I) is shown in Fig. 1. The acid and base molecules are held together by an O—H⋯N hydrogen bond between the carboxy group and the N atom of the base. In addition, a weak C—H⋯O interaction is formed between the acid and base molecules (Table 1). In the hydrogen-bonded acid–base unit, the quinoline ring system (N2/C8–C16), the carboxy group (O1/C7/O2) and the benzene ring (C1–C6) are almost coplanar with each other; the carboxy group makes dihedral angles of 9.95 (12) and 9.45 (12)°, respectively, with the quinoline ring system and the benzene ring, and the dihedral angle between the quinoline ring system and the benzene ring is 2.59 (4)°. On the other hand, the benzene ring and the nitro group (O3/N1/O4) in the acid molecule is almost perpendicular, with a dihedral angle of 86.14 (13)°. The quinoline ring system and the attached nitro group (O5/N3/O6) are somewhat twisted with a dihedral angle of 31.67 (11)°.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.88 (2)	1.80 (2)	2.6727 (12)	178 (2)
C8—H8⋯O2	0.95	2.48	3.1820 (13)	131
C5—H5⋯O2ⁱ	0.95	2.57	3.4860 (14)	163
C14—H14⋯O5ⁱ	0.95	2.56	3.4644 (14)	159
C13—H13⋯O6ⁱⁱ	0.95	2.32	3.1495 (14)	146
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of (I)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The O—H⋯N and C—H⋯O hydrogen bonds are indicated by dashed lines (Table 1

The molecular structure of (II) is shown in Fig. 2. Similar to (I), the acid and base molecules are held together by an O—H⋯N hydrogen bond and an additional C—H⋯O interaction (Table 2). In the acid–base unit, the quinoline ring system, the carboxy group and the benzene ring of the acid are slightly twisted to each other; the carboxy group makes dihedral angles of 12.08 (13) and 2.40 (13)°, respectively, with the quinoline ring system and the benzene ring, and the dihedral angle between the quinoline ring system and the benzene ring is 10.99 (4)°. In the acid molecule, the benzene ring and the nitro group (O3/N1/O4) are almost perpendicular with a dihedral angle of 88.54 (13)°. On the other hand, in the base molecule the quinoline ring system and the nitro group (O5/N3/O6) are almost coplanar with a dihedral angle of 5.58 (12)°.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.87 (3)	1.76 (3)	2.6310 (14)	176 (3)
C8—H8⋯O2	0.95	2.53	3.2082 (16)	128
C8—H8⋯O6ⁱ	0.95	2.41	3.2387 (15)	145
C12—H12⋯O5ⁱⁱ	0.95	2.37	3.2526 (16)	155
C14—H14⋯O4ⁱⁱⁱ	0.95	2.52	3.3226 (16)	142
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y, -z+1; (iii) x, y-1, z.

Figure 2
The molecular structure of (II)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The O—H⋯N and C—H⋯O hydrogen bonds are indicated by dashed lines (Table 2

The molecular structure of (III) is shown in Fig. 3. An acid–base interaction involving H-atom transfer occurs and the acid and base molecules are linked by an N⁺—H⋯O⁻ hydrogen bond (Table 3). In the hydrogen-bonded unit, the quinoline ring system makes dihedral angles of 34.96 (13) and 30.80 (14)°, respectively, with the carboxylate group and the benzene ring of the acid. In the acid molecule, the benzene ring makes dihedral angles of 4.71 (13) and 86.12 (11)°, respectively, with the carboxylate and nitro groups.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.880 (16)	1.776 (16)	2.6355 (12)	164.7 (14)
O5—H5O⋯O2ⁱ	0.872 (19)	1.756 (19)	2.6247 (12)	173.2 (19)
C4—H4⋯O3ⁱⁱ	0.95	2.49	3.1082 (12)	123
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Figure 3
The molecular structure of (III)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The N—H⋯O hydrogen bond is indicated by a dashed line (Table 3

3. Supramolecular features

In the crystal of (I), the hydrogen-bonded acid–base units are linked by C—H⋯O hydrogen bonds (C5—H5⋯O2ⁱ and C14—H14⋯O5ⁱ; symmetry codes as in Table 1), forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C—H⋯O hydrogen bond (C13—H13⋯O6ⁱⁱ), forming wide ribbons parallel to the ( $[\overline{1}]$ 03) plane (Fig. 4). These ribbons are stacked via π–π interactions between the quinoline ring systems, forming layers parallel to the ab plane (Fig. 5). The centroid–centroid distances are 3.4935 (5), 3.6761 (6) and 3.7721 (6) Å, respectively, for Cg4⋯Cg4ⁱⁱⁱ, Cg2⋯Cg2ⁱⁱⁱ and Cg2⋯Cg3ⁱⁱⁱ, where Cg2, Cg3 and Cg4 are the centroids of the N2/C8–C11/C16, C11–C16 and N2/C8–C16 rings, respectively, of the base molecule [symmetry code: (iii) −x + 1, y, −z + 2].

Figure 4
A packing diagram of (I)

, showing the hydrogen-bonded tape structure along the b-axis direction. Adjacent tapes, related by a twofold rotation axis, are linked by further C—H⋯O hydrogen bonds, forming wide ribbons parallel to ( $[\overline{1}]$ 03). The dashed lines indicate the O—H⋯N and C—H⋯O hydrogen bonds. [Symmetry codes: (i) x, y − 1, z; (ii) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

Figure 5
A partial packing diagram of (I)

, showing the ribbons linked by π–π stacking interactions (magenta dashed lines).

In the crystal of (II), the hydrogen-bonded acid–base units are also linked into a tape structure along the b-axis direction via C—H⋯O hydrogen bonds (C8—H8⋯O6ⁱ and C14—H14⋯O4ⁱⁱⁱ; symmetry codes as in Table 2). Inversion-related tapes are linked by a further C—H⋯O hydrogen bond (C12—H12⋯O5ⁱⁱ; Table 2), forming wide ribbons parallel to the ( $[\overline{3}]$ 08) plane (Fig. 6). The acid and base molecules are further stacked in a column along [ $[\overline{1}]$ 11] in an ⋯A⋯A⋯B⋯B⋯A⋯A⋯B⋯B⋯ manner (A: acid and B: base) via weak π–π interactions (Fig. 7), so forming a three-dimensional structure. The centroid–centroid distances are 3.8016 (8), 3.8666 (8), 3.9247 (9) and 3.8225 (8) Å, respectively, for Cg1⋯Cg1^iv, Cg1⋯Cg3^v, Cg2⋯Cg2^vi and Cg2⋯Cg4^vi, where Cg1, Cg2, Cg3 and Cg4 are, respectively, the centroids of the C1–C6 ring of the acid molecule, and the N2/C8–C11/C16, C11–C16 and N2/C8–C16 rings of the base molecule [symmetry codes: (iv) −x, −y + 2, −z; (v) x − 1, y + 1, z; (vi) −x + 1, −y + 1, −z + 1]. A pair of short O⋯N contacts [O6⋯N3^vii = 2.8453 (13) Å; symmetry code: (vii) −x + 1, −y, −x + 1] between the nitro groups of the base molecule are alsso observed.

Figure 6
A packing diagram of (II)

, showing the ribbon structure along the b-axis direction formed by O—H⋯N and C—H⋯O hydrogen bonds (dashed lines). H atoms not involved in the hydrogen bonds have been omitted. [Symmetry codes: (i) x, y + 1, z; (ii) −x + 2, −y, −z + 1; (iii) x, y − 1, z.]

Figure 7
A partial packing diagram of (II)

, showing the column structure along [ $[\overline{1}]$ 11] formed by weak π–π interactions (magenta dashed lines). The O—H⋯N and C—H⋯O hydrogen bonds in the hydrogen-bonded acid–base units are indicated by green dashed lines. The π–π interactions including the centroid of the ten-membered quinoline ring system (Cg4) are omitted for clarity.

In the crystal of compound (III), the cations and the anions are alternately linked via N—H⋯O and O—H⋯O hydrogen bonds (N2—H2⋯O1 and O5—H5O⋯O2ⁱ; symmetry code as in Table 3), forming a 2₁ helical chain running along the b-axis direction (Fig. 8). In the chain, a C—H⋯O (C4—H4⋯O3ⁱⁱ; Table 3) interaction formed between the anions and a π–π interaction between the C1–C6 ring and the C11–C16 ring are observed [Cg1⋯Cg3ⁱ = 3.5570 (6) Å]; Cg1 and Cg3 are, respectively, the centroids of the C1–C6 ring of the anion and the C11–C16 ring of the cation. In addition to the π–π interaction (Cg1⋯Cg3ⁱ), other π–π interactions are observed; the centroid–centroid distances are 3.5469 (6), 3.8550 (6) and 3.5133 (6) Å, respectively, for Cg1⋯Cg2ⁱⁱⁱ, Cg1⋯Cg3ⁱⁱⁱ and Cg1⋯Cg4ⁱⁱⁱ, where Cg2 and Cg4 are the centroids of the N2/C8–C11/C16 and N2/C8–C16 rings of the cation, respectively [symmetry code: (iii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ]. The cations and the anions are stacked alternately in columns along the a-axis direction via the π–π interactions (Fig. 9), and the molecular chains are linked into layers parallel to the ab plane through these interactions. A short Cl⋯O contact [Cl1⋯O3^iv = 3.0669 (10) Å; symmetry code: (iv) −x + 2, −y + 1, −z + 1] is observed between the layers.

Figure 8
A partial packing diagram of (III)

, showing the 2₁ helix running along the b-axis direction formed by O—H⋯O and N—H⋯O hydrogen bonds (black dashed lines). The C—H⋯O and π–π interactions observed in the chain are indicated by black and blue dashed lines, respectively. Cg1 and Cg3 are the centroids of the C1–C6 and C11–C16 rings, respectively. H atoms not involved in the hydrogen bonds have been omitted. [Symmetry codes: (i) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) x, y + 1, z.]

Figure 9
A partial packing diagram of (III)

, showing the π–π interactions (magenta dashed lines). The N—H⋯O hydrogen bonds in the hydrogen-bonded acid–base units are indicated by green dashed lines. Cg1, Cg2 and Cg3 are the centroids of the C1–C6, N2/C8–C11/C16 and C11–C16 rings, respectively. The π–π interactions including the centroid of the ten-membered quinoline ring system (Cg4) are omitted for clarity. [Symmetry codes: (i) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) x, y + 1, z; (iii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ .]

4. Database survey

A search of the Cambridge Structural Database (Version 5.40, last update May 2019; Groom et al., 2016 ) for organic co-crystals of 3-chloro-2-nitrobonzoic acid with base molecules gave six hits (five compounds), namely, 4-benzpylpyridine (1/1) (refcode UHAQUP; Sugiyama et al., 2002 ), quinolone (1/1) (AJIWOG; Gotoh & Ishida, 2009), phthalazine (1/1) (CALJUW; Gotoh & Ishida, 2011), isoquinoline (1/1) (NOVLAN; Gotoh & Ishida, 2015) and 4,4′-bipyridine (2/1) (XICGUO and XICGUO01; Rawat et al., 2018 ). The structure of 3-chloro-2-nitrobonzoic acid itself (XICHAV) was also reported by Rawat et al. (2018). There is no structure for a salt of 3-chloro-2-nitrobonzoic acid with an organic base molecule. In the acid molecules of the above compounds, the dihedral angles between the benzene ring and the nitro group, and between the benzene ring and the carboxy group are in the ranges 79.1 (3)–89.9 (3)° and 1.4 (3)–14.2 (3)°, respectively, which agree with those in the three title compounds. The ΔpK_a values for UHAQUP, AJIWOG, CALJUW, NOVLAN and XICGUO are 1.32, 3.08, 1.65, 3.58 and 3.27, respectively, and these compounds show short O⋯N distances in the O—H⋯N hydrogen bonds of 2.600 (3), 2.561 (1), 2.540 (2)–2.571 (2), 2.573 (1) and 2.613 (3) Å, respectively. Furthermore, in the short hydrogen bonds of AJIWOG, CALJUW and NOVLAN, the H atom is disordered over two positions. On the other hand, the compounds (I), (II) and (III) with ΔpK_a values of 0.98, 1.42 and 3.02, respectively, show longer O⋯N distances of 2.673 (1), 2.631 (1) and 2.636 (1) Å, which suggests that the ΔpK_a value is not an effective measure of hydrogen-bond strength in the 3-chloro-2-nitrobenzoic acid–organic base system.

A search for organic co-crystals/salts of 5-nitroquinoline showed six structures. Limiting the search to benzoic acid derivatives gave two hits, namely, 3-aminobenzoic acid–5-nitroquinoline (1/1) (PANYIM; Lynch et al., 1997 ) and 4-animobenzoic acid–5-nitroquinoline (1/2) (PANZEJ; Lynch et al., 1997). No structure was found in the CSD for organic co-crystals/salts of 6-nitroquinoline. A search for organic co-crystals/salts of 8-hydroxyquinoline gave 17 hits. Of these compounds, one related compound is 8-hydroxyquinolinium 2-chloro-4-nitrobenzoate (WOPDEM; Babu & Chandrasekaran, 2014 ; ΔpK_a = 2.80), in which the O⋯N distance of the N—H⋯O hydrogen bond is 2.644 (3) Å.

5. Synthesis and crystallization

Crystals of all three compounds, (I)–(III), were obtained by slow evaporation from acetonitrile solutions of 3-chloro-2-nitrobenzoic acid with quinoline derivatives in a 1:1 molar ratio at room temperature [100 ml acetonitrile solution of 3-chloro-2-nitrobenzoic acid (0.39 g) and 5-nitroquinoline (0.34 g) for (I), 150 ml acetonitrile solution of 3-chloro-2-nitrobenzoic acid (0.45 g) and 6-nitroquinoline (0.39 g) for (II), and 120 ml acetonitrile solution of 3-chloro-2-nitrobenzoic acid (0.55 g) and 8-hydroxyqunoline (0.40 mg) for (III)] .

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. All H atoms in compounds (I)–(III) were found in difference-Fourier maps. O- and N-bound H atoms in (I)–(III) were refined freely [refined distances: O1—H1 = 0.88 (2) Å in (I), N1—H1 = 0.87 (3) Å in (II), and N2—H2 = 0.880 (16) and O5—H5O = 0.872 (19) Å in (III),]. Other H atoms were positioned geometrically (C—H = 0.95 Å) and treated as riding, with U_iso(H) = 1.2U_eq(C).

Table 4
Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C₇H₄ClNO₄·C₉H₆N₂O₂	C₇H₄ClNO₄·C₉H₆N₂O₂	C₇H₃ClNO₄·C₉H₈NO
M_r	375.72	375.72	346.73
Crystal system, space group	Monoclinic, C2/c	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n
Temperature (K)	190	190	190
a, b, c (Å)	20.5876 (4), 7.6889 (3), 20.4312 (4)	7.7282 (10), 10.2839 (14), 11.2828 (16)	7.3409 (5), 7.4689 (4), 27.0427 (14)
α, β, γ (°)	90, 104.5338 (7), 90	71.990 (4), 79.724 (4), 69.051 (3)	90, 95.7158 (19), 90
V (Å³)	3130.70 (16)	794.08 (19)	1475.33 (15)
Z	8	2	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.29	0.28	0.29
Crystal size (mm)	0.45 × 0.40 × 0.30	0.38 × 0.35 × 0.30	0.45 × 0.30 × 0.26

Data collection
Diffractometer	Rigaku R-AXIS RAPIDII	Rigaku R-AXIS RAPIDII	Rigaku R-AXIS RAPIDII
Absorption correction	Numerical (NUMABS; Higashi, 1999 )	Numerical (NUMABS; Higashi, 1999)	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.837, 0.918	0.887, 0.919	0.844, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	30107, 4549, 4077	16549, 4622, 4029	29560, 4311, 3937
R_int	0.022	0.026	0.019
(sin θ/λ)_max (Å⁻¹)	0.703	0.703	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.05	0.039, 0.113, 1.07	0.033, 0.092, 1.06
No. of reflections	4549	4622	4311
No. of parameters	239	239	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35	0.50, −0.33	0.39, −0.30
Computer programs: RAPID-AUTO (Rigaku, 2006 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ), CrystalStructure (Rigaku, 2018 ) and PLATON (Spek, 2015 ).

Supporting information

CCDC references: 1953605; 1953604; 1953603

Crystal structure: contains datablocks global, I, II, III. DOI: https://doi.org/10.1107/S2056989019012799/lh5922sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019012799/lh5922Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019012799/lh5922IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989019012799/lh5922IIIsup4.hkl

checkCIF report

Computing details top

For all structures, data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2015).

3-Chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1) (I) top

Crystal data top

C₇H₄ClNO₄·C₉H₆N₂O₂	F(000) = 1536.00
M_r = 375.72	D_x = 1.594 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
a = 20.5876 (4) Å	Cell parameters from 25710 reflections
b = 7.6889 (3) Å	θ = 3.1–30.1°
c = 20.4312 (4) Å	µ = 0.29 mm⁻¹
β = 104.5338 (7)°	T = 190 K
V = 3130.70 (16) Å³	Block, colorless
Z = 8	0.45 × 0.40 × 0.30 mm

Data collection top

Rigaku R-AXIS RAPIDII diffractometer	4077 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.022
ω scans	θ_max = 30.0°, θ_min = 3.1°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −26→28
T_min = 0.837, T_max = 0.918	k = −10→10
30107 measured reflections	l = −28→28
4549 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: mixed
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0636P)² + 1.2587P] where P = (F_o² + 2F_c²)/3
4549 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.35 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
Cl1	0.03434 (2)	0.24994 (4)	0.50043 (2)	0.03753 (9)
O1	0.34832 (4)	0.34621 (10)	0.61778 (4)	0.03292 (17)
O2	0.27238 (4)	0.55880 (10)	0.60848 (5)	0.03766 (19)
O3	0.14558 (5)	0.57618 (11)	0.50150 (4)	0.0412 (2)
O4	0.12329 (5)	0.55420 (11)	0.59855 (5)	0.0414 (2)
O5	0.64633 (4)	0.97971 (11)	0.75715 (4)	0.03764 (19)
O6	0.72372 (4)	0.82403 (14)	0.73078 (5)	0.0472 (2)
N1	0.14396 (4)	0.49673 (11)	0.55218 (5)	0.02666 (17)
N2	0.43699 (4)	0.60692 (11)	0.64264 (4)	0.02613 (17)
N3	0.66566 (4)	0.84775 (12)	0.73417 (4)	0.02984 (18)
C1	0.23369 (5)	0.26976 (12)	0.58259 (5)	0.02307 (18)
C2	0.16614 (4)	0.31430 (12)	0.55708 (5)	0.02215 (17)
C3	0.11699 (5)	0.18860 (13)	0.53478 (5)	0.02620 (19)
C4	0.13470 (5)	0.01433 (14)	0.53907 (6)	0.0320 (2)
H4	0.101547	−0.072633	0.523966	0.038*
C5	0.20130 (6)	−0.03225 (14)	0.56561 (6)	0.0344 (2)
H5	0.213441	−0.151718	0.569282	0.041*
C6	0.25043 (5)	0.09415 (13)	0.58689 (6)	0.0296 (2)
H6	0.295828	0.060186	0.604524	0.035*
C7	0.28632 (5)	0.40747 (12)	0.60433 (5)	0.02479 (18)
C8	0.41075 (5)	0.76300 (13)	0.63187 (5)	0.0281 (2)
H8	0.363528	0.772862	0.614770	0.034*
C9	0.44900 (5)	0.91633 (13)	0.64438 (5)	0.0290 (2)
H9	0.427911	1.026448	0.634382	0.035*
C10	0.51692 (5)	0.90588 (12)	0.67109 (5)	0.02615 (19)
H10	0.543243	1.008630	0.680454	0.031*
C11	0.54753 (5)	0.74008 (11)	0.68461 (5)	0.02182 (17)
C12	0.61745 (5)	0.70585 (13)	0.71097 (5)	0.02475 (18)
C13	0.64371 (5)	0.54231 (14)	0.71854 (6)	0.0311 (2)
H13	0.690681	0.525741	0.735325	0.037*
C14	0.60078 (6)	0.39830 (14)	0.70133 (6)	0.0356 (2)
H14	0.618748	0.283873	0.706670	0.043*
C15	0.53282 (6)	0.42258 (13)	0.67677 (6)	0.0313 (2)
H15	0.504064	0.324562	0.665699	0.038*
C16	0.50536 (5)	0.59203 (12)	0.66783 (5)	0.02310 (18)
H1	0.3780 (11)	0.430 (3)	0.6264 (10)	0.073 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02113 (13)	0.03817 (16)	0.04799 (17)	−0.00501 (9)	−0.00126 (11)	−0.00276 (10)
O1	0.0197 (3)	0.0265 (4)	0.0495 (5)	−0.0024 (3)	0.0029 (3)	−0.0014 (3)
O2	0.0245 (4)	0.0230 (3)	0.0615 (5)	−0.0035 (3)	0.0033 (3)	−0.0040 (3)
O3	0.0537 (5)	0.0289 (4)	0.0359 (4)	0.0016 (3)	0.0018 (4)	0.0084 (3)
O4	0.0421 (5)	0.0322 (4)	0.0559 (5)	0.0007 (3)	0.0237 (4)	−0.0094 (4)
O5	0.0346 (4)	0.0320 (4)	0.0431 (4)	−0.0071 (3)	0.0037 (3)	−0.0078 (3)
O6	0.0214 (4)	0.0566 (6)	0.0631 (6)	−0.0097 (4)	0.0097 (4)	−0.0088 (5)
N1	0.0211 (4)	0.0221 (4)	0.0344 (4)	−0.0018 (3)	0.0025 (3)	−0.0014 (3)
N2	0.0195 (4)	0.0268 (4)	0.0299 (4)	−0.0039 (3)	0.0020 (3)	0.0007 (3)
N3	0.0221 (4)	0.0337 (4)	0.0314 (4)	−0.0067 (3)	0.0022 (3)	−0.0007 (3)
C1	0.0209 (4)	0.0210 (4)	0.0265 (4)	−0.0031 (3)	0.0044 (3)	−0.0008 (3)
C2	0.0215 (4)	0.0196 (4)	0.0248 (4)	−0.0018 (3)	0.0047 (3)	−0.0002 (3)
C3	0.0216 (4)	0.0260 (4)	0.0294 (4)	−0.0046 (3)	0.0036 (3)	−0.0019 (3)
C4	0.0300 (5)	0.0237 (5)	0.0405 (5)	−0.0075 (4)	0.0057 (4)	−0.0040 (4)
C5	0.0341 (5)	0.0196 (4)	0.0477 (6)	−0.0026 (4)	0.0068 (5)	−0.0018 (4)
C6	0.0259 (4)	0.0221 (4)	0.0391 (5)	0.0000 (3)	0.0050 (4)	−0.0001 (4)
C7	0.0200 (4)	0.0239 (4)	0.0290 (4)	−0.0032 (3)	0.0035 (3)	0.0002 (3)
C8	0.0197 (4)	0.0304 (5)	0.0321 (5)	−0.0014 (3)	0.0025 (4)	0.0042 (4)
C9	0.0245 (4)	0.0241 (4)	0.0369 (5)	0.0014 (3)	0.0053 (4)	0.0051 (4)
C10	0.0230 (4)	0.0216 (4)	0.0332 (5)	−0.0019 (3)	0.0059 (4)	0.0017 (3)
C11	0.0186 (4)	0.0219 (4)	0.0243 (4)	−0.0020 (3)	0.0042 (3)	−0.0004 (3)
C12	0.0187 (4)	0.0275 (4)	0.0267 (4)	−0.0030 (3)	0.0032 (3)	−0.0015 (3)
C13	0.0223 (4)	0.0319 (5)	0.0368 (5)	0.0049 (4)	0.0032 (4)	0.0004 (4)
C14	0.0325 (5)	0.0246 (5)	0.0470 (6)	0.0061 (4)	0.0047 (5)	−0.0010 (4)
C15	0.0287 (5)	0.0218 (4)	0.0409 (5)	−0.0016 (3)	0.0038 (4)	−0.0022 (4)
C16	0.0203 (4)	0.0220 (4)	0.0259 (4)	−0.0027 (3)	0.0037 (3)	−0.0007 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.7352 (10)	C5—C6	1.3913 (14)
O1—C7	1.3231 (12)	C5—H5	0.9500
O1—H1	0.88 (2)	C6—H6	0.9500
O2—C7	1.2065 (13)	C8—C9	1.4051 (14)
O3—N1	1.2099 (12)	C8—H8	0.9500
O4—N1	1.2150 (12)	C9—C10	1.3699 (13)
O5—N3	1.2256 (13)	C9—H9	0.9500
O6—N3	1.2282 (12)	C10—C11	1.4182 (13)
N1—C2	1.4708 (12)	C10—H10	0.9500
N2—C8	1.3118 (13)	C11—C16	1.4205 (12)
N2—C16	1.3768 (12)	C11—C12	1.4290 (13)
N3—C12	1.4711 (13)	C12—C13	1.3621 (14)
C1—C6	1.3909 (13)	C13—C14	1.4053 (16)
C1—C2	1.3997 (13)	C13—H13	0.9500
C1—C7	1.5002 (13)	C14—C15	1.3755 (16)
C2—C3	1.3909 (12)	C14—H14	0.9500
C3—C4	1.3857 (14)	C15—C16	1.4138 (13)
C4—C5	1.3889 (16)	C15—H15	0.9500
C4—H4	0.9500

C7—O1—H1	111.7 (14)	O1—C7—C1	113.43 (8)
O3—N1—O4	125.03 (10)	N2—C8—C9	123.28 (9)
O3—N1—C2	117.71 (9)	N2—C8—H8	118.4
O4—N1—C2	117.21 (9)	C9—C8—H8	118.4
C8—N2—C16	118.56 (8)	C10—C9—C8	119.51 (9)
O5—N3—O6	123.97 (9)	C10—C9—H9	120.2
O5—N3—C12	118.67 (8)	C8—C9—H9	120.2
O6—N3—C12	117.33 (9)	C9—C10—C11	119.32 (9)
C6—C1—C2	117.92 (8)	C9—C10—H10	120.3
C6—C1—C7	121.16 (9)	C11—C10—H10	120.3
C2—C1—C7	120.92 (8)	C10—C11—C16	117.28 (8)
C3—C2—C1	121.68 (9)	C10—C11—C12	126.54 (8)
C3—C2—N1	116.90 (8)	C16—C11—C12	116.12 (8)
C1—C2—N1	121.41 (8)	C13—C12—C11	123.12 (9)
C4—C3—C2	119.53 (9)	C13—C12—N3	115.57 (9)
C4—C3—Cl1	120.28 (7)	C11—C12—N3	121.28 (9)
C2—C3—Cl1	120.18 (8)	C12—C13—C14	119.48 (9)
C3—C4—C5	119.50 (9)	C12—C13—H13	120.3
C3—C4—H4	120.3	C14—C13—H13	120.3
C5—C4—H4	120.3	C15—C14—C13	120.17 (10)
C4—C5—C6	120.72 (10)	C15—C14—H14	119.9
C4—C5—H5	119.6	C13—C14—H14	119.9
C6—C5—H5	119.6	C14—C15—C16	120.63 (9)
C1—C6—C5	120.61 (10)	C14—C15—H15	119.7
C1—C6—H6	119.7	C16—C15—H15	119.7
C5—C6—H6	119.7	N2—C16—C15	117.59 (8)
O2—C7—O1	124.25 (9)	N2—C16—C11	121.96 (8)
O2—C7—C1	122.32 (9)	C15—C16—C11	120.46 (9)

C6—C1—C2—C3	−1.77 (14)	C8—C9—C10—C11	1.01 (15)
C7—C1—C2—C3	178.02 (9)	C9—C10—C11—C16	1.49 (14)
C6—C1—C2—N1	178.69 (9)	C9—C10—C11—C12	178.64 (9)
C7—C1—C2—N1	−1.53 (14)	C10—C11—C12—C13	−175.60 (10)
O3—N1—C2—C3	−92.47 (11)	C16—C11—C12—C13	1.57 (14)
O4—N1—C2—C3	85.14 (11)	C10—C11—C12—N3	6.67 (15)
O3—N1—C2—C1	87.09 (12)	C16—C11—C12—N3	−176.16 (8)
O4—N1—C2—C1	−95.29 (11)	O5—N3—C12—C13	−148.03 (10)
C1—C2—C3—C4	1.39 (15)	O6—N3—C12—C13	30.14 (14)
N1—C2—C3—C4	−179.05 (9)	O5—N3—C12—C11	29.86 (14)
C1—C2—C3—Cl1	−177.45 (7)	O6—N3—C12—C11	−151.97 (10)
N1—C2—C3—Cl1	2.11 (12)	C11—C12—C13—C14	−1.45 (16)
C2—C3—C4—C5	0.03 (16)	N3—C12—C13—C14	176.40 (10)
Cl1—C3—C4—C5	178.87 (9)	C12—C13—C14—C15	0.27 (18)
C3—C4—C5—C6	−1.02 (18)	C13—C14—C15—C16	0.68 (18)
C2—C1—C6—C5	0.76 (16)	C8—N2—C16—C15	−177.79 (10)
C7—C1—C6—C5	−179.03 (10)	C8—N2—C16—C11	2.30 (14)
C4—C5—C6—C1	0.62 (18)	C14—C15—C16—N2	179.60 (10)
C6—C1—C7—O2	−171.24 (11)	C14—C15—C16—C11	−0.50 (16)
C2—C1—C7—O2	8.99 (15)	C10—C11—C16—N2	−3.23 (14)
C6—C1—C7—O1	9.12 (14)	C12—C11—C16—N2	179.32 (8)
C2—C1—C7—O1	−170.66 (9)	C10—C11—C16—C15	176.87 (9)
C16—N2—C8—C9	0.41 (16)	C12—C11—C16—C15	−0.58 (14)
N2—C8—C9—C10	−2.09 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.88 (2)	1.80 (2)	2.6727 (12)	178 (2)
C8—H8···O2	0.95	2.48	3.1820 (13)	131
C5—H5···O2ⁱ	0.95	2.57	3.4860 (14)	163
C14—H14···O5ⁱ	0.95	2.56	3.4644 (14)	159
C13—H13···O6ⁱⁱ	0.95	2.32	3.1495 (14)	146

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

3-Chloro-2-nitrobenzoicacid–6-nitroquinoline (1/1) (II) top

Crystal data top

C₇H₄ClNO₄·C₉H₆N₂O₂	Z = 2
M_r = 375.72	F(000) = 384.00
Triclinic, P1	D_x = 1.571 Mg m⁻³
a = 7.7282 (10) Å	Mo Kα radiation, λ = 0.71075 Å
b = 10.2839 (14) Å	Cell parameters from 14524 reflections
c = 11.2828 (16) Å	θ = 3.1–30.1°
α = 71.990 (4)°	µ = 0.28 mm⁻¹
β = 79.724 (4)°	T = 190 K
γ = 69.051 (3)°	Block, colorless
V = 794.08 (19) Å³	0.38 × 0.35 × 0.30 mm

Data collection top

Rigaku R-AXIS RAPIDII diffractometer	4029 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.026
ω scans	θ_max = 30.0°, θ_min = 3.1°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −10→10
T_min = 0.887, T_max = 0.919	k = −14→14
16549 measured reflections	l = −15→15
4622 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: mixed
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.072P)² + 0.0976P] where P = (F_o² + 2F_c²)/3
4622 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.33 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
Cl1	−0.21217 (4)	1.44247 (3)	−0.00166 (3)	0.04778 (11)
O1	0.17321 (12)	0.77718 (8)	0.24868 (9)	0.03883 (19)
O2	0.30609 (12)	0.94833 (9)	0.20949 (10)	0.0464 (2)
O3	0.23107 (11)	1.23134 (10)	0.01395 (9)	0.0439 (2)
O4	0.12561 (13)	1.25965 (10)	0.19770 (10)	0.0477 (2)
O5	0.83957 (13)	−0.07571 (9)	0.45563 (10)	0.0469 (2)
O6	0.58065 (12)	−0.04120 (8)	0.38490 (8)	0.03651 (18)
N1	0.12435 (12)	1.22061 (9)	0.10689 (9)	0.03234 (19)
N2	0.50541 (13)	0.60187 (9)	0.31357 (9)	0.03239 (19)
N3	0.69185 (13)	0.00332 (9)	0.41169 (8)	0.03128 (18)
C1	−0.00331 (13)	1.01631 (10)	0.15345 (9)	0.02609 (18)
C2	−0.02570 (12)	1.16317 (10)	0.10624 (9)	0.02667 (18)
C3	−0.18851 (13)	1.26120 (10)	0.05510 (10)	0.0299 (2)
C4	−0.33392 (14)	1.21363 (12)	0.04976 (10)	0.0325 (2)
H4	−0.445873	1.280397	0.015146	0.039*
C5	−0.31344 (14)	1.06810 (12)	0.09541 (10)	0.0318 (2)
H5	−0.411793	1.034696	0.091986	0.038*
C6	−0.14952 (13)	0.97031 (11)	0.14634 (9)	0.02906 (19)
H6	−0.137031	0.870569	0.176756	0.035*
C7	0.17485 (14)	0.91108 (10)	0.20737 (10)	0.0302 (2)
C8	0.62786 (17)	0.65774 (11)	0.32741 (12)	0.0382 (2)
H8	0.593373	0.759863	0.309365	0.046*
C9	0.80676 (17)	0.57424 (13)	0.36745 (13)	0.0413 (3)
H9	0.890518	0.619663	0.374699	0.050*
C10	0.85796 (16)	0.42727 (12)	0.39567 (12)	0.0367 (2)
H10	0.977047	0.368770	0.424193	0.044*
C11	0.73037 (14)	0.36326 (10)	0.38169 (9)	0.02805 (19)
C12	0.77423 (14)	0.21193 (10)	0.40730 (10)	0.02926 (19)
H12	0.890452	0.148054	0.437393	0.035*
C13	0.64508 (14)	0.16024 (10)	0.38761 (9)	0.02718 (19)
C14	0.47039 (14)	0.24888 (11)	0.34310 (10)	0.0302 (2)
H14	0.385636	0.207883	0.329622	0.036*
C15	0.42557 (14)	0.39522 (11)	0.31976 (10)	0.0310 (2)
H15	0.307926	0.457014	0.290674	0.037*
C16	0.55426 (13)	0.45484 (10)	0.33887 (9)	0.02686 (18)
H1	0.285 (3)	0.723 (3)	0.270 (2)	0.089 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03623 (16)	0.02349 (14)	0.0773 (2)	−0.00733 (10)	−0.02054 (14)	0.00154 (12)
O1	0.0321 (4)	0.0222 (3)	0.0574 (5)	−0.0076 (3)	−0.0081 (3)	−0.0028 (3)
O2	0.0339 (4)	0.0274 (4)	0.0765 (6)	−0.0091 (3)	−0.0234 (4)	−0.0020 (4)
O3	0.0315 (4)	0.0410 (4)	0.0603 (5)	−0.0196 (3)	−0.0013 (4)	−0.0068 (4)
O4	0.0429 (5)	0.0451 (5)	0.0664 (6)	−0.0136 (4)	−0.0170 (4)	−0.0240 (4)
O5	0.0430 (4)	0.0235 (4)	0.0679 (6)	−0.0034 (3)	−0.0177 (4)	−0.0047 (4)
O6	0.0471 (4)	0.0304 (4)	0.0395 (4)	−0.0196 (3)	−0.0002 (3)	−0.0132 (3)
N1	0.0246 (4)	0.0221 (4)	0.0508 (5)	−0.0070 (3)	−0.0109 (4)	−0.0065 (3)
N2	0.0329 (4)	0.0204 (4)	0.0417 (5)	−0.0051 (3)	−0.0079 (3)	−0.0066 (3)
N3	0.0368 (4)	0.0225 (4)	0.0340 (4)	−0.0100 (3)	−0.0023 (3)	−0.0066 (3)
C1	0.0231 (4)	0.0236 (4)	0.0311 (4)	−0.0078 (3)	−0.0029 (3)	−0.0060 (3)
C2	0.0217 (4)	0.0244 (4)	0.0349 (4)	−0.0085 (3)	−0.0041 (3)	−0.0071 (3)
C3	0.0250 (4)	0.0238 (4)	0.0389 (5)	−0.0071 (3)	−0.0065 (4)	−0.0042 (4)
C4	0.0220 (4)	0.0342 (5)	0.0401 (5)	−0.0080 (4)	−0.0063 (4)	−0.0075 (4)
C5	0.0255 (4)	0.0365 (5)	0.0374 (5)	−0.0152 (4)	−0.0011 (4)	−0.0099 (4)
C6	0.0273 (4)	0.0282 (4)	0.0335 (4)	−0.0132 (4)	0.0008 (3)	−0.0075 (4)
C7	0.0287 (4)	0.0229 (4)	0.0370 (5)	−0.0068 (3)	−0.0050 (4)	−0.0054 (3)
C8	0.0433 (6)	0.0228 (4)	0.0506 (6)	−0.0102 (4)	−0.0097 (5)	−0.0097 (4)
C9	0.0420 (6)	0.0310 (5)	0.0588 (7)	−0.0157 (4)	−0.0144 (5)	−0.0122 (5)
C10	0.0328 (5)	0.0294 (5)	0.0518 (6)	−0.0100 (4)	−0.0144 (4)	−0.0099 (4)
C11	0.0282 (4)	0.0229 (4)	0.0343 (5)	−0.0078 (3)	−0.0074 (3)	−0.0071 (3)
C12	0.0269 (4)	0.0218 (4)	0.0373 (5)	−0.0048 (3)	−0.0091 (4)	−0.0054 (3)
C13	0.0303 (4)	0.0204 (4)	0.0307 (4)	−0.0082 (3)	−0.0044 (3)	−0.0055 (3)
C14	0.0298 (4)	0.0270 (4)	0.0359 (5)	−0.0115 (4)	−0.0083 (4)	−0.0055 (4)
C15	0.0270 (4)	0.0258 (4)	0.0385 (5)	−0.0068 (3)	−0.0103 (4)	−0.0041 (4)
C16	0.0275 (4)	0.0210 (4)	0.0309 (4)	−0.0064 (3)	−0.0054 (3)	−0.0053 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.7257 (10)	C5—C6	1.3921 (14)
O1—C7	1.3142 (12)	C5—H5	0.9500
O1—H1	0.87 (3)	C6—H6	0.9500
O2—C7	1.2117 (13)	C8—C9	1.4096 (16)
O3—N1	1.2153 (13)	C8—H8	0.9500
O4—N1	1.2132 (13)	C9—C10	1.3646 (15)
O5—N3	1.2243 (12)	C9—H9	0.9500
O6—N3	1.2244 (12)	C10—C11	1.4193 (14)
N1—C2	1.4796 (12)	C10—H10	0.9500
N2—C8	1.3218 (14)	C11—C12	1.4142 (13)
N2—C16	1.3688 (12)	C11—C16	1.4175 (13)
N3—C13	1.4682 (12)	C12—C13	1.3637 (14)
C1—C2	1.3940 (13)	C12—H12	0.9500
C1—C6	1.3947 (13)	C13—C14	1.4088 (13)
C1—C7	1.5044 (13)	C14—C15	1.3671 (14)
C2—C3	1.3873 (13)	C14—H14	0.9500
C3—C4	1.3934 (13)	C15—C16	1.4163 (14)
C4—C5	1.3832 (15)	C15—H15	0.9500
C4—H4	0.9500

C7—O1—H1	107.0 (16)	O1—C7—C1	113.28 (9)
O4—N1—O3	125.19 (9)	N2—C8—C9	123.66 (10)
O4—N1—C2	117.34 (9)	N2—C8—H8	118.2
O3—N1—C2	117.37 (9)	C9—C8—H8	118.2
C8—N2—C16	118.54 (9)	C10—C9—C8	119.08 (10)
O5—N3—O6	123.52 (9)	C10—C9—H9	120.5
O5—N3—C13	118.83 (9)	C8—C9—H9	120.5
O6—N3—C13	117.64 (9)	C9—C10—C11	118.90 (10)
C2—C1—C6	117.80 (9)	C9—C10—H10	120.5
C2—C1—C7	120.79 (8)	C11—C10—H10	120.5
C6—C1—C7	121.39 (8)	C12—C11—C16	119.20 (9)
C3—C2—C1	121.41 (9)	C12—C11—C10	122.22 (9)
C3—C2—N1	117.24 (8)	C16—C11—C10	118.57 (9)
C1—C2—N1	121.35 (8)	C13—C12—C11	118.16 (9)
C2—C3—C4	120.06 (9)	C13—C12—H12	120.9
C2—C3—Cl1	120.21 (7)	C11—C12—H12	120.9
C4—C3—Cl1	119.73 (8)	C12—C13—C14	123.80 (9)
C5—C4—C3	119.26 (9)	C12—C13—N3	118.24 (9)
C5—C4—H4	120.4	C14—C13—N3	117.95 (8)
C3—C4—H4	120.4	C15—C14—C13	118.50 (9)
C4—C5—C6	120.36 (9)	C15—C14—H14	120.8
C4—C5—H5	119.8	C13—C14—H14	120.8
C6—C5—H5	119.8	C14—C15—C16	120.10 (9)
C5—C6—C1	121.10 (9)	C14—C15—H15	120.0
C5—C6—H6	119.4	C16—C15—H15	119.9
C1—C6—H6	119.4	N2—C16—C15	118.54 (9)
O2—C7—O1	124.46 (9)	N2—C16—C11	121.22 (9)
O2—C7—C1	122.25 (9)	C15—C16—C11	120.23 (9)

C6—C1—C2—C3	0.76 (15)	N2—C8—C9—C10	−1.0 (2)
C7—C1—C2—C3	179.34 (9)	C8—C9—C10—C11	1.07 (19)
C6—C1—C2—N1	−178.31 (9)	C9—C10—C11—C12	179.07 (11)
C7—C1—C2—N1	0.27 (15)	C9—C10—C11—C16	−0.01 (17)
O4—N1—C2—C3	90.22 (12)	C16—C11—C12—C13	1.04 (15)
O3—N1—C2—C3	−86.34 (12)	C10—C11—C12—C13	−178.04 (10)
O4—N1—C2—C1	−90.67 (12)	C11—C12—C13—C14	0.05 (16)
O3—N1—C2—C1	92.76 (12)	C11—C12—C13—N3	178.77 (9)
C1—C2—C3—C4	−0.19 (16)	O5—N3—C13—C12	4.41 (15)
N1—C2—C3—C4	178.92 (9)	O6—N3—C13—C12	−174.69 (9)
C1—C2—C3—Cl1	179.61 (8)	O5—N3—C13—C14	−176.79 (10)
N1—C2—C3—Cl1	−1.28 (14)	O6—N3—C13—C14	4.11 (14)
C2—C3—C4—C5	−0.26 (16)	C12—C13—C14—C15	−0.97 (16)
Cl1—C3—C4—C5	179.94 (8)	N3—C13—C14—C15	−179.70 (9)
C3—C4—C5—C6	0.12 (16)	C13—C14—C15—C16	0.76 (15)
C4—C5—C6—C1	0.48 (15)	C8—N2—C16—C15	−177.77 (10)
C2—C1—C6—C5	−0.90 (14)	C8—N2—C16—C11	1.38 (15)
C7—C1—C6—C5	−179.48 (9)	C14—C15—C16—N2	179.46 (9)
C2—C1—C7—O2	−1.69 (16)	C14—C15—C16—C11	0.30 (15)
C6—C1—C7—O2	176.84 (11)	C12—C11—C16—N2	179.64 (9)
C2—C1—C7—O1	179.50 (9)	C10—C11—C16—N2	−1.25 (15)
C6—C1—C7—O1	−1.96 (14)	C12—C11—C16—C15	−1.22 (15)
C16—N2—C8—C9	−0.26 (18)	C10—C11—C16—C15	177.89 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.87 (3)	1.76 (3)	2.6310 (14)	176 (3)
C8—H8···O2	0.95	2.53	3.2082 (16)	128
C8—H8···O6ⁱ	0.95	2.41	3.2387 (15)	145
C14—H14···O4ⁱⁱ	0.95	2.52	3.3226 (16)	142
C12—H12···O5ⁱⁱⁱ	0.95	2.37	3.2526 (16)	155

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

8-Hydroxyquinoliniumb 3-chloro-2-nitrobenzoate (III) top

Crystal data top

C₇H₃ClNO₄·C₉H₈NO	F(000) = 712.00
M_r = 346.73	D_x = 1.561 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
a = 7.3409 (5) Å	Cell parameters from 25520 reflections
b = 7.4689 (4) Å	θ = 3.0–30.0°
c = 27.0427 (14) Å	µ = 0.29 mm⁻¹
β = 95.7158 (19)°	T = 190 K
V = 1475.33 (15) Å³	Block, pale yellow
Z = 4	0.45 × 0.30 × 0.26 mm

Data collection top

Rigaku R-AXIS RAPIDII diffractometer	3937 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.019
ω scans	θ_max = 30.0°, θ_min = 3.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −10→10
T_min = 0.844, T_max = 0.927	k = −10→10
29560 measured reflections	l = −37→37
4311 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: mixed
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0517P)² + 0.422P] where P = (F_o² + 2F_c²)/3
4311 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 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
Cl1	0.86076 (4)	0.71237 (3)	0.49827 (2)	0.03111 (8)
O1	0.49893 (14)	0.57049 (11)	0.27915 (3)	0.0388 (2)
O2	0.50879 (12)	0.37292 (10)	0.34157 (3)	0.03253 (18)
O3	0.81650 (12)	0.34758 (10)	0.42238 (3)	0.03453 (19)
O4	0.56116 (14)	0.41075 (12)	0.45203 (3)	0.0406 (2)
O5	0.25608 (11)	0.64218 (10)	0.18109 (3)	0.03011 (17)
N1	0.68835 (12)	0.44696 (11)	0.42827 (3)	0.02456 (17)
N2	0.41002 (11)	0.32651 (12)	0.21056 (3)	0.02279 (16)
C1	0.63355 (12)	0.66248 (12)	0.35750 (3)	0.02025 (17)
C2	0.69708 (12)	0.62802 (12)	0.40684 (3)	0.01940 (16)
C3	0.77981 (12)	0.76019 (13)	0.43755 (3)	0.02089 (17)
C4	0.80144 (13)	0.93180 (13)	0.41926 (4)	0.02407 (18)
H4	0.857461	1.022784	0.440109	0.029*
C5	0.74011 (14)	0.96853 (13)	0.37014 (4)	0.02617 (19)
H5	0.754706	1.085267	0.357150	0.031*
C6	0.65741 (13)	0.83530 (13)	0.33982 (4)	0.02399 (18)
H6	0.616164	0.862693	0.306263	0.029*
C7	0.53938 (13)	0.52246 (13)	0.32319 (4)	0.02389 (18)
C8	0.47845 (15)	0.17222 (14)	0.22785 (4)	0.0276 (2)
H8	0.530731	0.164820	0.261364	0.033*
C9	0.47520 (16)	0.02008 (14)	0.19773 (4)	0.0314 (2)
H9	0.520396	−0.091226	0.210789	0.038*
C10	0.40556 (15)	0.03461 (14)	0.14900 (4)	0.0292 (2)
H10	0.404556	−0.067323	0.127964	0.035*
C11	0.33516 (13)	0.19899 (13)	0.12955 (4)	0.02402 (19)
C12	0.26151 (15)	0.22187 (16)	0.07953 (4)	0.0303 (2)
H12	0.260234	0.124767	0.056813	0.036*
C13	0.19225 (15)	0.38479 (17)	0.06420 (4)	0.0317 (2)
H13	0.145274	0.400180	0.030447	0.038*
C14	0.18881 (14)	0.53056 (16)	0.09724 (4)	0.0287 (2)
H14	0.138468	0.641773	0.085598	0.034*
C15	0.25798 (13)	0.51294 (13)	0.14634 (4)	0.02325 (18)
C16	0.33572 (12)	0.34640 (13)	0.16246 (3)	0.02087 (17)
H2	0.421 (2)	0.417 (2)	0.2315 (6)	0.044 (4)*
H5O	0.173 (3)	0.722 (2)	0.1717 (7)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.04386 (16)	0.02719 (13)	0.02051 (12)	−0.00200 (9)	−0.00565 (9)	−0.00222 (8)
O1	0.0621 (6)	0.0278 (4)	0.0233 (4)	−0.0053 (4)	−0.0116 (3)	−0.0018 (3)
O2	0.0403 (4)	0.0219 (3)	0.0328 (4)	−0.0084 (3)	−0.0092 (3)	0.0002 (3)
O3	0.0389 (4)	0.0186 (3)	0.0436 (5)	0.0042 (3)	−0.0082 (3)	0.0010 (3)
O4	0.0546 (5)	0.0327 (4)	0.0368 (4)	−0.0104 (4)	0.0154 (4)	0.0047 (3)
O5	0.0389 (4)	0.0219 (3)	0.0282 (4)	0.0071 (3)	−0.0033 (3)	−0.0022 (3)
N1	0.0342 (4)	0.0172 (3)	0.0211 (4)	−0.0033 (3)	−0.0036 (3)	0.0004 (3)
N2	0.0267 (4)	0.0202 (4)	0.0214 (4)	0.0002 (3)	0.0019 (3)	−0.0013 (3)
C1	0.0217 (4)	0.0178 (4)	0.0206 (4)	0.0009 (3)	−0.0011 (3)	−0.0016 (3)
C2	0.0219 (4)	0.0152 (4)	0.0208 (4)	0.0006 (3)	0.0008 (3)	0.0002 (3)
C3	0.0228 (4)	0.0187 (4)	0.0206 (4)	0.0012 (3)	−0.0007 (3)	−0.0023 (3)
C4	0.0256 (4)	0.0165 (4)	0.0292 (5)	−0.0006 (3)	−0.0022 (3)	−0.0030 (3)
C5	0.0300 (5)	0.0161 (4)	0.0315 (5)	0.0002 (3)	−0.0013 (4)	0.0023 (3)
C6	0.0277 (4)	0.0194 (4)	0.0240 (4)	0.0016 (3)	−0.0016 (3)	0.0025 (3)
C7	0.0263 (4)	0.0205 (4)	0.0236 (4)	0.0007 (3)	−0.0040 (3)	−0.0032 (3)
C8	0.0318 (5)	0.0250 (5)	0.0259 (4)	0.0026 (4)	0.0025 (4)	0.0029 (4)
C9	0.0361 (5)	0.0219 (5)	0.0368 (5)	0.0044 (4)	0.0066 (4)	0.0014 (4)
C10	0.0321 (5)	0.0219 (4)	0.0348 (5)	−0.0013 (4)	0.0090 (4)	−0.0065 (4)
C11	0.0228 (4)	0.0249 (4)	0.0249 (4)	−0.0035 (3)	0.0053 (3)	−0.0040 (3)
C12	0.0300 (5)	0.0367 (6)	0.0246 (5)	−0.0062 (4)	0.0042 (4)	−0.0083 (4)
C13	0.0289 (5)	0.0450 (6)	0.0207 (4)	−0.0029 (4)	0.0002 (3)	−0.0003 (4)
C14	0.0272 (4)	0.0335 (5)	0.0251 (5)	0.0015 (4)	0.0012 (4)	0.0054 (4)
C15	0.0232 (4)	0.0229 (4)	0.0237 (4)	−0.0004 (3)	0.0024 (3)	0.0006 (3)
C16	0.0202 (4)	0.0212 (4)	0.0214 (4)	−0.0019 (3)	0.0030 (3)	−0.0010 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.7268 (10)	C5—C6	1.3898 (14)
O1—C7	1.2511 (12)	C5—H5	0.9500
O2—C7	1.2519 (13)	C6—H6	0.9500
O3—N1	1.2211 (12)	C8—C9	1.3969 (15)
O4—N1	1.2154 (12)	C8—H8	0.9500
O5—C15	1.3483 (12)	C9—C10	1.3695 (16)
O5—H5O	0.872 (19)	C9—H9	0.9500
N1—C2	1.4751 (12)	C10—C11	1.4132 (15)
N2—C8	1.3236 (13)	C10—H10	0.9500
N2—C16	1.3676 (12)	C11—C16	1.4154 (13)
N2—H2	0.880 (16)	C11—C12	1.4161 (14)
C1—C2	1.3930 (12)	C12—C13	1.3671 (17)
C1—C6	1.3935 (13)	C12—H12	0.9500
C1—C7	1.5180 (13)	C13—C14	1.4103 (16)
C2—C3	1.3902 (12)	C13—H13	0.9500
C3—C4	1.3887 (13)	C14—C15	1.3798 (14)
C4—C5	1.3870 (14)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.4189 (13)

C15—O5—H5O	109.9 (12)	N2—C8—C9	121.23 (10)
O4—N1—O3	125.17 (9)	N2—C8—H8	119.4
O4—N1—C2	118.51 (9)	C9—C8—H8	119.4
O3—N1—C2	116.22 (9)	C10—C9—C8	118.66 (10)
C8—N2—C16	122.14 (9)	C10—C9—H9	120.7
C8—N2—H2	115.9 (11)	C8—C9—H9	120.7
C16—N2—H2	121.9 (11)	C9—C10—C11	120.97 (9)
C2—C1—C6	117.27 (8)	C9—C10—H10	119.5
C2—C1—C7	123.14 (8)	C11—C10—H10	119.5
C6—C1—C7	119.58 (8)	C10—C11—C16	117.63 (9)
C3—C2—C1	121.72 (8)	C10—C11—C12	123.44 (9)
C3—C2—N1	116.73 (8)	C16—C11—C12	118.92 (9)
C1—C2—N1	121.48 (8)	C13—C12—C11	119.49 (10)
C4—C3—C2	120.08 (9)	C13—C12—H12	120.3
C4—C3—Cl1	119.26 (7)	C11—C12—H12	120.3
C2—C3—Cl1	120.64 (7)	C12—C13—C14	121.63 (10)
C5—C4—C3	119.08 (9)	C12—C13—H13	119.2
C5—C4—H4	120.5	C14—C13—H13	119.2
C3—C4—H4	120.5	C15—C14—C13	120.53 (10)
C4—C5—C6	120.29 (9)	C15—C14—H14	119.7
C4—C5—H5	119.9	C13—C14—H14	119.7
C6—C5—H5	119.9	O5—C15—C14	125.04 (9)
C5—C6—C1	121.56 (9)	O5—C15—C16	116.43 (8)
C5—C6—H6	119.2	C14—C15—C16	118.52 (9)
C1—C6—H6	119.2	N2—C16—C11	119.30 (9)
O1—C7—O2	126.78 (9)	N2—C16—C15	119.84 (8)
O1—C7—C1	115.77 (9)	C11—C16—C15	120.85 (9)
O2—C7—C1	117.44 (8)

C6—C1—C2—C3	0.47 (14)	C16—N2—C8—C9	−1.11 (16)
C7—C1—C2—C3	−178.81 (9)	N2—C8—C9—C10	2.40 (16)
C6—C1—C2—N1	−176.32 (8)	C8—C9—C10—C11	−1.12 (16)
C7—C1—C2—N1	4.41 (14)	C9—C10—C11—C16	−1.33 (15)
O4—N1—C2—C3	85.64 (11)	C9—C10—C11—C12	−179.99 (10)
O3—N1—C2—C3	−91.03 (11)	C10—C11—C12—C13	178.41 (10)
O4—N1—C2—C1	−97.42 (11)	C16—C11—C12—C13	−0.23 (14)
O3—N1—C2—C1	85.91 (11)	C11—C12—C13—C14	−1.28 (16)
C1—C2—C3—C4	−0.17 (14)	C12—C13—C14—C15	0.76 (16)
N1—C2—C3—C4	176.76 (8)	C13—C14—C15—O5	−177.90 (10)
C1—C2—C3—Cl1	−178.87 (7)	C13—C14—C15—C16	1.27 (15)
N1—C2—C3—Cl1	−1.94 (12)	C8—N2—C16—C11	−1.46 (14)
C2—C3—C4—C5	−0.23 (14)	C8—N2—C16—C15	177.62 (9)
Cl1—C3—C4—C5	178.49 (8)	C10—C11—C16—N2	2.62 (13)
C3—C4—C5—C6	0.32 (15)	C12—C11—C16—N2	−178.66 (9)
C4—C5—C6—C1	−0.01 (15)	C10—C11—C16—C15	−176.45 (9)
C2—C1—C6—C5	−0.38 (14)	C12—C11—C16—C15	2.27 (14)
C7—C1—C6—C5	178.92 (9)	O5—C15—C16—N2	−2.60 (13)
C2—C1—C7—O1	−176.23 (9)	C14—C15—C16—N2	178.16 (9)
C6—C1—C7—O1	4.51 (14)	O5—C15—C16—C11	176.47 (8)
C2—C1—C7—O2	4.37 (14)	C14—C15—C16—C11	−2.77 (14)
C6—C1—C7—O2	−174.89 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.880 (16)	1.776 (16)	2.6355 (12)	164.7 (14)
O5—H5O···O2ⁱ	0.872 (19)	1.756 (19)	2.6247 (12)	173.2 (19)
C4—H4···O3ⁱⁱ	0.95	2.49	3.1082 (12)	123

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

References

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Volume 75| Part 10| October 2019| Pages 1552-1557

https://doi.org/10.1107/S2056989019012799

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

Crystal structures of 3-chloro-2-nitro­benzoic acid with quinoline derivatives: 3-chloro-2-nitro­benzoic acid–5-nitro­quinoline (1/1), 3-chloro-2-nitro­benzoic acid–6-nitro­quinoline (1/1) and 8-hy­dr­oxy­quinolinium 3-chloro-2-nitro­benzoate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

References

research communications

Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives: 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid–6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate

3. Supramolecular features