π-Stacked hydrogen-bonded dimers in 2-(2-nitro­phenyl­amino­carbonyl)­benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitro­phenyl­amino­carbonyl)­benzoic acid

Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C₁₄H₁₀N₂O₅, are linked into centrosymmetric R(8) dimers by a single O—H...O hydrogen bond [H...O = 1.78 Å, O...O = 2.623 (2) Å and O—H...O = 178°] and these dimers are linked into sheets by a single aromatic π–π stacking interaction. The isomeric compound 2-(4-nitrophenylaminocarbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P2₁2₁2₁ with Z′ = 1, crystallized from ethanol), the mol­ecules are linked into sheets of R(22) rings by a combination of one N—H...O hydrogen bond [H...O = 1.96 Å, N...O = 2.833 (3) Å and N—H...O = 171°] and one O—H...O hydrogen bond [H...O = 1.78 Å, O...O = 2.614 (3) Å and O—H...O = 173°]. In the monoclinic form (space group P2₁/n with Z′ = 2, crystallized from acetone), the mol­ecules are linked by a combination of two N—H...O hydrogen bonds [H...O = 2.09 and 2.16 Å, N...O = 2.873 (4) and 2.902 (3) Å, and N—H...O = 147 and 141°] and two O—H...O hydrogen bonds [H...O = 1.84 and 1.83 Å, O...O = 2.664 (3) and 2.666 (3) Å, and O—H...O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C—H...O hydrogen bond [H...O = 2.45 Å, C...O = 3.355 (4) Å and C—­H...O = 160°].

S1. Comment

The reaction of C-substituted anilines with phthalic anhydride initially yields N-arylbenzamide-2-carboxylic acids, (A) (see Scheme). Dehydration of this type of intermediate yields N-arylphthalimides, (B), while hydrolysis yields arylammonium hydrogenphthalates, (C). We have recently reported the supramolecular structure of a type (C) salt, 4-iodoanilinium 3-nitrophthalate(1-) (Glidewell et al., 2003), and here we report the molecular and supramolecular structures of two examples of the type (A) intermediate, namely N-(2-nitrophenyl)benzamide-2-carboxylic acid, (I) (Fig. 1) and two polymorphs of N-(4-nitrophenyl)benzamide-2-carboxylic acid, orthorhombic, (II), (Fig. 2) and monoclinic, (III) (Fig. 3). \sch

In each of compounds (I)-(III), the central C11—C17(O17)—N1—C21 fragment of the molecule is essentially planar, with a trans amide conformation. The C11—C16 and C21—C26 rings are considerably rotated away from this plane, as indicated by the key torsion angles (Tables 1, 3 and 5). In (I), the carboxyl and nitro groups make dihedral angles of 29.9 (2) and 36.5 (2)°, respectively, with the adjacent aryl rings, and in (II) the corresponding angles are 12.2 (2) and 11.1 (2)°, respectively. In (III), these dihedral angles are 7.7 (2) and 13.0 (2)°, respectively, in molecule A, and 10.1 (2) and 6.5 (1)°, respectively, in molecule B. The C—O distances in the carboxyl groups are consistent with the location of the fully ordered carboxyl H atoms, as identified from difference maps. The other bond distances and angles show no exceptional features.

In compound (I) (Fig. 1), there is an intramolecular N—H···O hydrogen bond forming an S(6) motif (Bernstein et al., 1995). The supramolecular aggregation is dominated by a single O—H···O hydrogen bond, propagated by aromatic π–π stacking interactions. Carboxyl atom O11 in the molecule at (x, y, z) acts as hydrogen-bond donor to carboxyl atom O12 in the molecule at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric dimer characterized by the usual R₂²(8) motif and centred at (1/2, 1/2, 1/2) (Fig. 4).

The π–π stacking interaction involves the nitro-substituted ring of the molecule at (x, y, z), which is part of the dimer centred at (1/2, 1/2, 1/2), and the corresponding rings of the molecules at (1/2 + x, y, 3/2 − z) and (x − 1/2, y, 3/2 − z), which themselves are components of the dimers centred at (1, 1/2, 1) and (0, 1/2, 1), respectively. The interplanar angle between adjacent rings of this type is ca 9.5°, with a centroid separation of 3.793 (2) Å and an interplanar spacing of ca 3.42 Å. Propagation by inversion of this interaction also links the (1/2, 1/2, 1/2) dimer to those centred at (0, 1/2, 0) and (1, 1/2, 0), and hence the R₂²(8) dimers are linked into an (010) sheet (Fig. 5).

Whereas the supramolecular structure of (I) is controlled by a combination of O—H···O hydrogen bonds and aromatic π–π stacking interactions, while the N—H bond participates only in an intramolecular hydrogen bond, the supramolecular aggregation in the polymorphic compounds (II) and (III) is controlled by a combination of N—H···O and O—H···O hydrogen bonds. While π–π stacking interactions and X—H···π(arene) hydrogen bonds (X is C, N or O) are all absent from the structures of (II) and (III), there are two C—H···O hydrogen bonds present in (III).

In compound (II), the amidic atom N1 in the molecule at (x, y, z) acts as hydrogen-bond donor to carboxyl atom O12 in the molecule at (x − 1, y, z), so generating by translation a C(7) chain running parallel to the [100] direction. At the same time, carboxyl atom O11 at (x, y, z) acts as hydrogen-bond donor to amidic atom O17 in the molecule at (1 − x, 1/2 + y, 1/2 − z), so producing a spiral C(7) chain running parallel to the [010] direction and generated by the 2₁ screw axis along (1/2, y, 1/4). It is noteworthy that the carboxyl group in (II) forms neither of the motifs so characteristic of simple carboxylic acids, namely the R₂²(8) dimer [cf. compound (I)] and the C(4) chain. Likewise, the amide group in (II) does not form the C(4) chain often found in simple carboxylic amides, but instead each of the two hydrogen bonds in (II) utilizes a donor and an acceptor from the different functional groups, acid and amide, within the molecule.

The combination of the two C(7) chains in (II) generates an (001) sheet in the form of a hydrogen-bonded (4,4) net (Batten & Robson 1998) built from a single type of R₄⁴(22) ring (Fig. 6). This sheet lies in the domain −0.03 < z < 0.53 and a second such sheet lies in the domain 0.47 < z < 1.03, but there are no direction-specific interactions between adjacent sheets.

The supramolecular structure of the monoclinic form, (III), consists of sheets generated by a combination of O—H···O and N—H···O hydrogen bonds, linked into a three-dimensional framework by a single rather strong C—H···O hydrogen bond (Table 6). Carboxyl atom O11A acts as hydrogen-bond donor to amidic atom O17B within the asymmetric unit (Fig. 3) and, in a similar fashion, carboxyl atom O11B in the type B molecule at (x, y, z) acts as hydrogen-bond donor to amidic atom O17A in the type A molecule at (x, 1 + y, z). These two hydrogen bonds thus generate by translation a C₂²(14) chain running parallel to the [010] direction (Fig. 7). These translational chains are then linked into (001) sheets by the two N—H···O hydrogen bonds.

Amino atom N1A in the type A molecule at (x, y, z) acts as hydrogen-bond donor to carboxyl atom O12B in the type B molecule at (1/2 − x, y − 1/2, 1/2 − z), so producing a second C₂²(14) chain parallel to [010], this time generated by the 2₁ screw axis along (1/4, y, 1/4) (Fig. 8). Similarly, amino atom N1B at (x, y, z) acts as hydrogen-bond donor to carboxyl atom O12A at (3/2 − x, 1/2 + y, 1/2 − z), so producing a third C₂²(14) chain, this time generated by the 2₁ screw axis along (3/4, y, 1/4).

The combination of these three C₂²(14) chains generates an (001) sheet lying in the domain −0.02 < z < 0.52, and a second such sheet, related to the first by inversion, lies in the domain 0.48 < z < 1.02. The sheet is reinforced by a C—H···O hydrogen bond (Table 6) and adjacent sheets are linked by a second C—H···O hydrogen bond. Atom C23B in the type B molecule at (x, y, z), which lies in the −0.02 < z < 0.52 sheet, acts as hydrogen-bond donor to nitro atom O41A in the type A molecule at (1/2 + x, 1/2 − y, 1/2 + z), which forms part of the sheet in the domain 0.48 < z < 1.02. Propagation of this interaction by the space group then generates a single three-dimensional framework.

S2. Experimental

Samples of both acids were prepared by heating, under reflux, chloroform solutions containing equimolar mixtures of phthalic anhydride and the appropriate nitroaniline. The reactions were monitored by thin-layer chromatography and when they were complete, the mixtures were cooled and the solvent was removed. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in ethanol for (I) and (II), and in acetone for (III). Melting point for (I) 426–428 K; for (II) 475–477 K with liberation of water, followed rapidly by re-solidification on formation of N-(4-nitrophenyl)phthalimide and subsequent re-melting at 528–531 K; for (III) 471–473 K with liberation of water, followed rapidly by re-solidification as for (II).

S3. Refinement

For compounds (I), (II) and (III), the space groups Pbca, P2₁2₁2₁ and P2₁/n, respectively, were uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with distances C—H = 0.95, N—H = 0.88 and O—H = 0.84 Å. In the absence of significant anomalous scattering, the absolute configuration of (II) could not be established. However, this has no chemical significance and the Friedel equivalents were merged. Conventional refinement of (II) led to R = 0.0945 with maximum residual density of 1.632, and examination of the refined structure of (II) using PLATON (Spek, 2003) revealed two voids, each of volume ca 89 ų, centred at approximately (0, 1/4, 1/2) and (0, 3/4 0). The electron density within these voids could not be interpreted in terms of any sensible model of solvent molecules, and accordingly the reflection data were subjected to the SQUEEZE option in PLATON before the final refinements. This procedure suggested the presence of only 6–7 electrons per unit cell within the voids. Examination of the refined structure of (III) using PLATON also revealed two symmetry-related void spaces per unit cell, each of approximate volume 63 ų, centred at (0, 1/2, 0) and (1/2, 0, 1/2), although the residual densities from the refinement were very low. Accordingly, a supernumerary O atom was placed near the centre of the void and its site-occupancy factor was refined, giving a value of 0.045 (6), indicative of negligible electron density within the void.

Computing details

For all compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (I), (II); OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997) for (III). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I), (II); OSCAIL and SHELXL97 (Sheldrick, 1997) for (III). For all compounds, molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecule of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. The two independent molecules in compound (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 4. Part of the crystal structure of (I), showing formation of a centrosymmetric R2^2(8) dimer. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
	Fig. 5. Stereoview of part of the crystal structure of (I), showing the linking of the hydrogen-bonded dimers into an (010) sheet by means of the aromatic π–π stacking interaction. For the sake of clarity, H atoms bonded to C or N atoms have been omitted.
	Fig. 6. Stereoview of part of the crystal structure of (II), showing the formation of an (001) sheet of R4^4(22) rings. For the sake of clarity, H atoms bonded to C atoms have been omitted.
	Fig. 7. Part of the crystal structure of (III), showing the C2^2(14) chain generated by translation. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (x, 1 + y, z) and (x, y − 1, z), respectively.
	Fig. 8. Stereoview of part of the crystal structure of (III), showing the C2^2(14) chains generated by translation and by the 21 screw axis along (1/4, y, 1/4). For the sake of clarity, H atoms bonded to C atoms have been omitted.

(I) 2-(2-nitrophenylaminocarbonyl)benzoic acid

Crystal data

C14H10N2O5	F(000) = 1184
Mr = 286.24	Dx = 1.523 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2848 reflections
a = 7.2761 (2) Å	θ = 3.2–27.5°
b = 14.8881 (5) Å	µ = 0.12 mm^−1
c = 23.0407 (6) Å	T = 120 K
V = 2495.94 (13) Å^3	Block, colourless
Z = 8	0.36 × 0.36 × 0.22 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2848 independent reflections
Radiation source: rotating anode	1876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −7→9
Tmin = 0.955, Tmax = 0.975	k = −19→19
15224 measured reflections	l = −27→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0595P)^2] where P = (Fo^2 + 2Fc^2)/3
2848 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3912 (2)	0.66212 (10)	0.68329 (6)	0.0184 (4)
C11	0.3660 (2)	0.73886 (12)	0.59102 (7)	0.0178 (4)
C12	0.4161 (2)	0.71745 (12)	0.53395 (7)	0.0181 (4)
C13	0.4467 (3)	0.78557 (13)	0.49395 (8)	0.0218 (4)
C14	0.4313 (3)	0.87494 (13)	0.51080 (8)	0.0251 (5)
C15	0.3856 (3)	0.89625 (13)	0.56740 (8)	0.0263 (5)
C16	0.3511 (3)	0.82848 (13)	0.60725 (8)	0.0237 (4)
C17	0.3014 (3)	0.66598 (12)	0.63142 (7)	0.0188 (4)
C18	0.4502 (3)	0.62202 (12)	0.51827 (7)	0.0196 (4)
O11	0.4224 (2)	0.60281 (9)	0.46339 (5)	0.0280 (3)
O12	0.50338 (18)	0.56741 (8)	0.55444 (5)	0.0260 (3)
O17	0.17176 (18)	0.61778 (9)	0.61845 (5)	0.0247 (3)
C21	0.3487 (2)	0.60095 (12)	0.72837 (7)	0.0174 (4)
C22	0.3474 (2)	0.62663 (12)	0.78658 (7)	0.0178 (4)
C23	0.3015 (2)	0.56789 (13)	0.83106 (8)	0.0214 (4)
C24	0.2588 (3)	0.48019 (12)	0.81765 (8)	0.0230 (4)
C25	0.2599 (3)	0.45285 (13)	0.76019 (8)	0.0231 (4)
C26	0.3027 (2)	0.51244 (12)	0.71581 (8)	0.0215 (4)
N22	0.3928 (2)	0.71871 (10)	0.80312 (7)	0.0216 (4)
O21	0.3086 (2)	0.75267 (9)	0.84359 (6)	0.0332 (4)
O22	0.51459 (18)	0.75869 (8)	0.77559 (5)	0.0249 (3)
H1	0.4708	0.7052	0.6904	0.022*
H13	0.4781	0.7711	0.4550	0.026*
H14	0.4523	0.9215	0.4834	0.030*
H15	0.3779	0.9574	0.5790	0.032*
H16	0.3171	0.8434	0.6459	0.028*
H11	0.4481	0.5486	0.4574	0.042*
H23	0.2995	0.5879	0.8702	0.026*
H24	0.2288	0.4388	0.8476	0.028*
H25	0.2309	0.3923	0.7510	0.028*
H26	0.3005	0.4926	0.6766	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0210 (8)	0.0171 (8)	0.0171 (8)	−0.0037 (7)	0.0001 (6)	0.0010 (6)
O17	0.0268 (8)	0.0262 (8)	0.0212 (7)	−0.0056 (6)	−0.0025 (5)	0.0024 (6)
C11	0.0180 (10)	0.0186 (10)	0.0168 (9)	0.0000 (8)	−0.0011 (7)	0.0013 (7)
C12	0.0186 (10)	0.0179 (9)	0.0179 (9)	0.0002 (8)	−0.0021 (7)	0.0003 (7)
C13	0.0248 (11)	0.0240 (11)	0.0165 (9)	0.0005 (9)	0.0012 (7)	0.0020 (7)
C14	0.0300 (12)	0.0207 (11)	0.0247 (10)	−0.0029 (9)	0.0004 (8)	0.0069 (8)
C15	0.0342 (12)	0.0162 (10)	0.0285 (11)	0.0010 (9)	−0.0009 (8)	0.0002 (8)
C16	0.0308 (11)	0.0194 (10)	0.0209 (10)	0.0009 (8)	0.0026 (8)	−0.0021 (8)
C17	0.0219 (11)	0.0175 (10)	0.0168 (9)	0.0023 (8)	0.0020 (7)	−0.0028 (7)
C18	0.0198 (10)	0.0221 (11)	0.0170 (9)	−0.0002 (8)	0.0020 (7)	0.0000 (8)
O11	0.0463 (9)	0.0214 (7)	0.0165 (7)	0.0077 (7)	−0.0026 (6)	−0.0047 (5)
O12	0.0393 (9)	0.0208 (7)	0.0179 (7)	0.0061 (6)	−0.0005 (6)	−0.0004 (5)
O17	0.0268 (8)	0.0262 (8)	0.0212 (7)	−0.0056 (6)	−0.0025 (5)	0.0024 (6)
C21	0.0157 (9)	0.0173 (9)	0.0190 (9)	0.0025 (8)	0.0010 (7)	0.0026 (7)
C22	0.0168 (10)	0.0146 (9)	0.0221 (9)	0.0023 (7)	−0.0011 (7)	−0.0008 (7)
C23	0.0217 (11)	0.0242 (11)	0.0183 (9)	0.0023 (8)	0.0008 (7)	0.0021 (8)
C24	0.0238 (10)	0.0212 (10)	0.0239 (10)	0.0002 (9)	0.0009 (8)	0.0072 (8)
C25	0.0235 (11)	0.0162 (9)	0.0297 (11)	−0.0012 (8)	−0.0008 (8)	0.0014 (8)
C26	0.0235 (11)	0.0200 (10)	0.0210 (9)	0.0020 (8)	−0.0007 (8)	−0.0017 (8)
N22	0.0254 (9)	0.0196 (8)	0.0197 (8)	0.0017 (7)	−0.0035 (7)	0.0013 (7)
O21	0.0483 (10)	0.0249 (8)	0.0265 (8)	0.0018 (7)	0.0097 (6)	−0.0059 (6)
O22	0.0298 (8)	0.0198 (7)	0.0250 (7)	−0.0051 (6)	−0.0005 (6)	0.0028 (5)

Geometric parameters (Å, º)

N1—C17	1.363 (2)	C18—O11	1.312 (2)
N1—C21	1.416 (2)	C18—O12	1.227 (2)
N1—H1	0.88	O11—H11	0.84
C17—O17	1.222 (2)	C21—C26	1.390 (3)
C17—C11	1.505 (2)	C21—C22	1.395 (2)
C11—C16	1.390 (3)	C22—C23	1.388 (2)
C11—C12	1.401 (2)	C22—N22	1.461 (2)
C12—C13	1.388 (3)	C23—C24	1.377 (3)
C12—C18	1.487 (2)	C23—H23	0.95
C13—C14	1.390 (3)	C24—C25	1.385 (3)
C13—H13	0.95	C24—H24	0.95
C14—C15	1.383 (3)	C25—C26	1.389 (3)
C14—H14	0.95	C25—H25	0.95
C15—C16	1.387 (3)	C26—H26	0.95
C15—H15	0.95	N22—O21	1.2248 (19)
C16—H16	0.95	N22—O22	1.2417 (19)
C17—N1—C21	124.45 (15)	O12—C18—C12	121.38 (15)
C17—N1—H1	116.7	O11—C18—C12	114.63 (15)
C21—N1—H1	118.4	C18—O11—H11	109.5
O17—C17—N1	124.01 (16)	C26—C21—C22	117.30 (16)
O17—C17—C11	120.89 (16)	C26—C21—N1	120.64 (15)
N1—C17—C11	115.01 (16)	C22—C21—N1	122.05 (16)
C16—C11—C12	119.41 (16)	C23—C22—C21	122.61 (17)
C16—C11—C17	120.08 (15)	C23—C22—N22	116.94 (15)
C12—C11—C17	119.85 (16)	C21—C22—N22	120.44 (15)
C13—C12—C11	119.90 (17)	C24—C23—C22	119.07 (17)
C13—C12—C18	120.67 (16)	C24—C23—H23	120.5
C11—C12—C18	119.26 (15)	C22—C23—H23	120.5
C12—C13—C14	120.06 (17)	C23—C24—C25	119.46 (17)
C12—C13—H13	120.0	C23—C24—H24	120.3
C14—C13—H13	120.0	C25—C24—H24	120.3
C15—C14—C13	120.14 (17)	C24—C25—C26	121.14 (18)
C15—C14—H14	119.9	C24—C25—H25	119.4
C13—C14—H14	119.9	C26—C25—H25	119.4
C14—C15—C16	120.07 (18)	C25—C26—C21	120.40 (17)
C14—C15—H15	120.0	C25—C26—H26	119.8
C16—C15—H15	120.0	C21—C26—H26	119.8
C15—C16—C11	120.39 (17)	O21—N22—O22	123.22 (15)
C15—C16—H16	119.8	O21—N22—C22	118.22 (15)
C11—C16—H16	119.8	O22—N22—C22	118.56 (14)
O12—C18—O11	123.97 (16)
C12—C11—C17—N1	127.5 (2)	C17—C11—C16—C15	−170.79 (18)
C11—C17—N1—C21	177.8 (2)	C13—C12—C18—O12	147.44 (19)
C17—N1—C21—C22	−139.1 (2)	C11—C12—C18—O12	−27.8 (3)
C11—C12—C18—O11	153.6 (2)	C13—C12—C18—O11	−31.2 (2)
C21—C22—N22—O21	143.3 (2)	C17—N1—C21—C26	39.6 (3)
C21—N1—C17—O17	1.2 (3)	C26—C21—C22—C23	−0.4 (3)
O17—C17—C11—C16	114.8 (2)	N1—C21—C22—C23	178.34 (17)
N1—C17—C11—C16	−61.8 (2)	C26—C21—C22—N22	−179.53 (16)
O17—C17—C11—C12	−55.9 (2)	N1—C21—C22—N22	−0.8 (3)
C16—C11—C12—C13	−1.3 (3)	C21—C22—C23—C24	1.3 (3)
C17—C11—C12—C13	169.45 (17)	N22—C22—C23—C24	−179.56 (16)
C16—C11—C12—C18	173.92 (17)	C22—C23—C24—C25	−1.0 (3)
C17—C11—C12—C18	−15.3 (3)	C23—C24—C25—C26	−0.2 (3)
C11—C12—C13—C14	1.4 (3)	C24—C25—C26—C21	1.1 (3)
C18—C12—C13—C14	−173.82 (18)	C22—C21—C26—C25	−0.8 (3)
C12—C13—C14—C15	0.0 (3)	N1—C21—C26—C25	−179.56 (16)
C13—C14—C15—C16	−1.4 (3)	C23—C22—N22—O21	−35.9 (2)
C14—C15—C16—C11	1.4 (3)	C23—C22—N22—O22	144.11 (16)
C12—C11—C16—C15	0.0 (3)	C21—C22—N22—O22	−36.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O22	0.88	2.14	2.719 (2)	123
O11—H11···O12^i	0.84	1.78	2.623 (2)	178

Symmetry code: (i) −x+1, −y+1, −z+1.

(II) 2-(4-nitrophenylaminocarbonyl)benzoic acid

Crystal data

C14H10N2O5	F(000) = 592
Mr = 286.24	Dx = 1.380 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1820 reflections
a = 3.9188 (2) Å	θ = 3.2–27.5°
b = 12.6896 (6) Å	µ = 0.11 mm^−1
c = 27.7029 (16) Å	T = 120 K
V = 1377.61 (12) Å^3	Needle, colourless
Z = 4	0.25 × 0.08 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1820 independent reflections
Radiation source: rotating anode	1237 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −5→5
Tmin = 0.969, Tmax = 0.996	k = −16→16
4875 measured reflections	l = −35→35

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0583P)^2] where P = (Fo^2 + 2Fc^2)/3
1820 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4342 (8)	0.5589 (2)	0.70323 (8)	0.0303 (7)
C11	0.5423 (9)	0.5098 (2)	0.78643 (10)	0.0269 (8)
C12	0.6198 (10)	0.6014 (2)	0.81186 (10)	0.0270 (8)
C13	0.5374 (10)	0.6055 (3)	0.86087 (11)	0.0348 (9)
C14	0.3895 (10)	0.5198 (3)	0.88373 (11)	0.0394 (9)
C15	0.3207 (11)	0.4297 (3)	0.85830 (11)	0.0407 (9)
C16	0.3992 (10)	0.4238 (2)	0.80935 (11)	0.0335 (8)
C17	0.6123 (10)	0.4948 (3)	0.73279 (11)	0.0320 (9)
C18	0.8051 (9)	0.6899 (2)	0.78949 (10)	0.0270 (8)
O11	0.8145 (7)	0.77547 (16)	0.81683 (7)	0.0388 (7)
O12	0.9420 (6)	0.68670 (16)	0.74998 (7)	0.0303 (6)
O17	0.8074 (7)	0.42565 (17)	0.71936 (7)	0.0408 (6)
C21	0.4494 (9)	0.5637 (2)	0.65252 (10)	0.0294 (8)
C22	0.5861 (10)	0.4840 (3)	0.62427 (11)	0.0348 (9)
C23	0.5869 (10)	0.4974 (3)	0.57478 (11)	0.0408 (10)
C24	0.4558 (10)	0.5856 (3)	0.55435 (11)	0.0380 (9)
C25	0.3161 (10)	0.6659 (3)	0.58184 (10)	0.0384 (9)
C26	0.3130 (10)	0.6534 (3)	0.63148 (10)	0.0326 (8)
N24	0.4617 (9)	0.5952 (3)	0.50187 (10)	0.0490 (9)
O41	0.2980 (9)	0.6661 (3)	0.48315 (8)	0.0670 (9)
O42	0.6302 (9)	0.5322 (3)	0.47881 (9)	0.0713 (10)
H1	0.3011	0.6027	0.7191	0.036*
H13	0.5833	0.6678	0.8787	0.042*
H14	0.3357	0.5236	0.9171	0.047*
H15	0.2191	0.3711	0.8741	0.049*
H16	0.3546	0.3609	0.7918	0.040*
H11	0.9303	0.8223	0.8030	0.058*
H22	0.6768	0.4220	0.6385	0.042*
H23	0.6807	0.4440	0.5548	0.049*
H25	0.2254	0.7274	0.5671	0.046*
H26	0.2166	0.7068	0.6513	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0354 (17)	0.0342 (16)	0.0213 (11)	0.0063 (14)	0.0026 (12)	0.0005 (11)
C17	0.031 (2)	0.033 (2)	0.0321 (16)	−0.0053 (19)	−0.0054 (16)	−0.0002 (15)
O17	0.0467 (17)	0.0321 (13)	0.0436 (13)	0.0134 (14)	−0.0009 (12)	−0.0053 (11)
C11	0.029 (2)	0.0275 (18)	0.0248 (14)	0.0009 (16)	−0.0014 (14)	0.0036 (13)
C12	0.028 (2)	0.0254 (17)	0.0273 (15)	0.0033 (16)	−0.0022 (15)	0.0057 (13)
C13	0.038 (2)	0.040 (2)	0.0263 (16)	−0.0037 (18)	−0.0016 (15)	0.0015 (15)
C14	0.044 (3)	0.049 (2)	0.0248 (14)	−0.003 (2)	−0.0025 (17)	0.0062 (15)
C15	0.041 (2)	0.041 (2)	0.0394 (18)	−0.010 (2)	−0.0057 (19)	0.0194 (17)
C16	0.037 (2)	0.0275 (18)	0.0359 (17)	−0.0024 (18)	−0.0105 (17)	0.0078 (14)
C18	0.029 (2)	0.0282 (17)	0.0241 (14)	0.0044 (16)	−0.0028 (15)	0.0010 (14)
O11	0.0563 (18)	0.0265 (12)	0.0335 (11)	−0.0076 (13)	0.0133 (12)	−0.0053 (10)
O12	0.0360 (15)	0.0309 (13)	0.0240 (10)	0.0023 (11)	0.0071 (10)	0.0013 (9)
C21	0.027 (2)	0.037 (2)	0.0247 (14)	−0.0039 (18)	−0.0024 (15)	−0.0021 (14)
C22	0.039 (2)	0.0323 (19)	0.0332 (16)	0.0051 (18)	0.0027 (18)	−0.0046 (14)
C23	0.040 (2)	0.052 (2)	0.0300 (16)	0.001 (2)	0.0024 (18)	−0.0166 (16)
C24	0.036 (2)	0.058 (2)	0.0199 (14)	−0.011 (2)	−0.0019 (15)	−0.0013 (16)
C25	0.043 (2)	0.047 (2)	0.0253 (14)	−0.002 (2)	−0.0010 (17)	0.0041 (15)
C26	0.037 (2)	0.0377 (19)	0.0235 (14)	−0.0017 (19)	0.0006 (16)	−0.0034 (13)
N24	0.043 (2)	0.078 (3)	0.0253 (15)	−0.013 (2)	−0.0015 (15)	−0.0057 (16)
O41	0.087 (2)	0.089 (2)	0.0251 (11)	−0.013 (2)	−0.0089 (15)	0.0074 (14)
O42	0.064 (2)	0.120 (3)	0.0302 (12)	0.004 (2)	0.0058 (15)	−0.0213 (15)

Geometric parameters (Å, º)

N1—C17	1.349 (4)	C18—O11	1.324 (3)
N1—C21	1.408 (4)	C18—O12	1.219 (3)
N1—H1	0.88	O11—H11	0.84
C17—O17	1.222 (4)	C21—C22	1.386 (4)
C17—C11	1.523 (4)	C21—C26	1.386 (4)
C11—C16	1.382 (4)	C22—C23	1.381 (4)
C11—C12	1.393 (4)	C22—H22	0.95
C12—C13	1.397 (4)	C23—C24	1.355 (5)
C12—C18	1.474 (4)	C23—H23	0.95
C13—C14	1.386 (5)	C24—C25	1.385 (5)
C13—H13	0.95	C24—N24	1.459 (4)
C14—C15	1.370 (4)	C25—C26	1.384 (4)
C14—H14	0.95	C25—H25	0.95
C15—C16	1.393 (5)	C26—H26	0.95
C15—H15	0.95	N24—O42	1.218 (4)
C16—H16	0.95	N24—O41	1.220 (4)
C17—N1—C21	127.6 (3)	O12—C18—C12	124.6 (3)
C17—N1—H1	112.6	O11—C18—C12	113.4 (2)
C21—N1—H1	119.8	C18—O11—H11	109.5
O17—C17—N1	124.9 (3)	C22—C21—C26	120.7 (3)
O17—C17—C11	120.0 (3)	C22—C21—N1	123.3 (3)
N1—C17—C11	115.1 (3)	C26—C21—N1	116.0 (3)
C16—C11—C12	121.0 (3)	C23—C22—C21	118.1 (3)
C16—C11—C17	115.0 (3)	C23—C22—H22	120.9
C12—C11—C17	124.0 (3)	C21—C22—H22	120.9
C11—C12—C13	118.2 (3)	C24—C23—C22	121.0 (3)
C11—C12—C18	122.1 (3)	C24—C23—H23	119.5
C13—C12—C18	119.6 (3)	C22—C23—H23	119.5
C14—C13—C12	120.8 (3)	C23—C24—C25	121.8 (3)
C14—C13—H13	119.6	C23—C24—N24	118.6 (3)
C12—C13—H13	119.6	C25—C24—N24	119.5 (3)
C15—C14—C13	120.2 (3)	C26—C25—C24	117.8 (3)
C15—C14—H14	119.9	C26—C25—H25	121.1
C13—C14—H14	119.9	C24—C25—H25	121.1
C14—C15—C16	120.2 (3)	C25—C26—C21	120.5 (3)
C14—C15—H15	119.9	C25—C26—H26	119.7
C16—C15—H15	119.9	C21—C26—H26	119.7
C11—C16—C15	119.6 (3)	O42—N24—O41	123.1 (3)
C11—C16—H16	120.2	O42—N24—C24	118.4 (4)
C15—C16—H16	120.2	O41—N24—C24	118.5 (3)
O12—C18—O11	121.9 (3)
C12—C11—C17—N1	−64.8 (5)	C11—C12—C18—O11	171.2 (3)
C11—C17—N1—C21	179.1 (3)	C23—C24—N24—O41	168.8 (4)
C17—N1—C21—C22	17.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O12^i	0.88	1.96	2.833 (3)	171
O11—H11···O17^ii	0.84	1.78	2.614 (3)	173

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

(III) 2-(4-nitrophenylaminocarbonyl)benzoic acid

Crystal data

C14H10N2O5	F(000) = 1184
Mr = 286.24	Dx = 1.474 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5503 reflections
a = 10.2098 (10) Å	θ = 3.0–27.4°
b = 9.3749 (8) Å	µ = 0.11 mm^−1
c = 27.409 (2) Å	T = 120 K
β = 100.578 (4)°	Plate, colourless
V = 2578.9 (4) Å^3	0.22 × 0.18 × 0.10 mm
Z = 8

Data collection

Nonius KappaCCD area-detector diffractometer	5503 independent reflections
Radiation source: rotating anode	2662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
ϕ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −11→12
Tmin = 0.965, Tmax = 0.989	k = −12→11
19240 measured reflections	l = −35→35

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0716P)^2] where P = (Fo^2 + 2Fc^2)/3
5503 reflections	(Δ/σ)max < 0.001
381 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11A	0.2819 (3)	0.0940 (3)	0.30113 (9)	0.0268 (7)
C12A	0.3602 (3)	0.2060 (3)	0.32469 (9)	0.0239 (7)
C13A	0.3627 (3)	0.2318 (3)	0.37481 (10)	0.0288 (8)
C14A	0.2898 (3)	0.1477 (3)	0.40118 (10)	0.0346 (8)
C15A	0.2168 (3)	0.0352 (3)	0.37854 (10)	0.0366 (9)
C16A	0.2114 (3)	0.0083 (3)	0.32880 (10)	0.0307 (8)
C18A	0.4469 (3)	0.2866 (3)	0.29669 (10)	0.0273 (7)
O11A	0.5270 (2)	0.3773 (2)	0.32449 (7)	0.0356 (6)
O12A	0.4477 (2)	0.2687 (2)	0.25270 (6)	0.0298 (5)
C17A	0.2761 (3)	0.0595 (3)	0.24733 (10)	0.0272 (7)
O17A	0.3441 (2)	−0.0374 (2)	0.23465 (6)	0.0335 (6)
N1A	0.1865 (3)	0.1368 (2)	0.21587 (8)	0.0281 (6)
C21A	0.1682 (3)	0.1401 (3)	0.16406 (10)	0.0267 (8)
C22A	0.2701 (3)	0.1091 (3)	0.13835 (10)	0.0310 (8)
C23A	0.2456 (4)	0.1155 (3)	0.08729 (11)	0.0402 (9)
C24A	0.1199 (4)	0.1527 (3)	0.06263 (11)	0.0415 (10)
C25A	0.0178 (4)	0.1843 (3)	0.08723 (10)	0.0386 (9)
C26A	0.0425 (3)	0.1794 (3)	0.13827 (10)	0.0329 (8)
N24A	0.0929 (5)	0.1578 (3)	0.00837 (11)	0.0626 (12)
O41A	0.1897 (4)	0.1542 (3)	−0.01303 (9)	0.0869 (12)
O42A	−0.0234 (4)	0.1652 (3)	−0.01317 (9)	0.0812 (12)
C11B	0.7592 (3)	0.5837 (3)	0.20613 (10)	0.0252 (7)
C12B	0.6580 (3)	0.6660 (3)	0.17796 (9)	0.0250 (7)
C13B	0.6527 (3)	0.6808 (3)	0.12706 (10)	0.0283 (8)
C14B	0.7479 (3)	0.6161 (3)	0.10455 (10)	0.0303 (8)
C15B	0.8471 (3)	0.5355 (3)	0.13237 (10)	0.0305 (8)
C16B	0.8537 (3)	0.5177 (3)	0.18256 (10)	0.0290 (8)
C18B	0.5577 (3)	0.7361 (3)	0.20288 (10)	0.0265 (7)
O11B	0.4810 (2)	0.8287 (2)	0.17438 (6)	0.0335 (6)
O12B	0.5477 (2)	0.7108 (2)	0.24543 (7)	0.0306 (5)
C17B	0.7660 (3)	0.5572 (3)	0.26046 (10)	0.0257 (7)
O17B	0.7182 (2)	0.4479 (2)	0.27463 (6)	0.0308 (5)
N1B	0.8348 (3)	0.6565 (2)	0.29067 (8)	0.0278 (6)
C21B	0.8544 (3)	0.6668 (3)	0.34262 (9)	0.0243 (7)
C22B	0.8215 (3)	0.5588 (3)	0.37331 (10)	0.0282 (7)
C23B	0.8455 (3)	0.5783 (3)	0.42414 (10)	0.0322 (8)
C24B	0.9009 (3)	0.7043 (3)	0.44392 (10)	0.0327 (8)
C25B	0.9350 (3)	0.8112 (3)	0.41438 (10)	0.0314 (8)
C26B	0.9125 (3)	0.7919 (3)	0.36378 (10)	0.0287 (8)
N24B	0.9234 (3)	0.7250 (3)	0.49769 (9)	0.0428 (8)
O41B	0.9035 (3)	0.6260 (3)	0.52431 (8)	0.0567 (8)
O42B	0.9610 (3)	0.8420 (3)	0.51405 (8)	0.0732 (10)
H13A	0.4151	0.3079	0.3909	0.035*
H14A	0.2899	0.1677	0.4352	0.042*
H15A	0.1697	−0.0247	0.3973	0.044*
H16A	0.1594	−0.0689	0.3133	0.037*
H11A	0.5804	0.4124	0.3078	0.043*
H1A	0.1332	0.1916	0.2295	0.034*
H22A	0.3560	0.0837	0.1559	0.037*
H23A	0.3143	0.0946	0.0693	0.048*
H25A	−0.0680	0.2089	0.0694	0.046*
H26A	−0.0262	0.2029	0.1560	0.039*
H13B	0.5835	0.7353	0.1078	0.034*
H14B	0.7448	0.6274	0.0699	0.036*
H15B	0.9121	0.4914	0.1166	0.037*
H16B	0.9222	0.4608	0.2012	0.035*
H11B	0.4355	0.8748	0.1916	0.040*
H1B	0.8725	0.7240	0.2757	0.033*
H22B	0.7829	0.4724	0.3593	0.034*
H23B	0.8238	0.5053	0.4453	0.039*
H25B	0.9736	0.8972	0.4287	0.038*
H26B	0.9368	0.8648	0.3430	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11A	0.022 (2)	0.0279 (18)	0.0317 (15)	0.0041 (15)	0.0081 (13)	−0.0014 (13)
C12A	0.018 (2)	0.0224 (16)	0.0325 (15)	0.0055 (14)	0.0090 (13)	0.0011 (12)
C13A	0.026 (2)	0.0265 (17)	0.0346 (16)	−0.0005 (15)	0.0067 (14)	−0.0017 (13)
C14A	0.033 (3)	0.044 (2)	0.0294 (15)	−0.0033 (17)	0.0121 (14)	−0.0026 (14)
C15A	0.036 (3)	0.040 (2)	0.0357 (17)	−0.0069 (17)	0.0128 (15)	0.0042 (14)
C16A	0.025 (2)	0.0298 (18)	0.0372 (17)	−0.0056 (15)	0.0056 (14)	−0.0018 (13)
C18A	0.025 (2)	0.0253 (17)	0.0321 (16)	0.0014 (15)	0.0056 (13)	−0.0003 (13)
O11A	0.0370 (18)	0.0333 (13)	0.0406 (11)	−0.0149 (11)	0.0180 (10)	−0.0067 (10)
O12A	0.0240 (16)	0.0362 (13)	0.0304 (11)	0.0018 (10)	0.0084 (9)	0.0002 (9)
C17A	0.021 (2)	0.0297 (18)	0.0317 (16)	−0.0039 (15)	0.0068 (14)	−0.0020 (13)
O17A	0.0324 (17)	0.0328 (13)	0.0374 (11)	0.0062 (11)	0.0118 (10)	−0.0026 (9)
N1A	0.0210 (18)	0.0355 (15)	0.0285 (12)	0.0050 (13)	0.0069 (11)	−0.0033 (11)
C21A	0.026 (2)	0.0245 (17)	0.0309 (15)	−0.0011 (14)	0.0078 (14)	−0.0006 (12)
C22A	0.030 (2)	0.0252 (17)	0.0401 (17)	0.0014 (15)	0.0125 (15)	0.0001 (13)
C23A	0.055 (3)	0.0288 (19)	0.0430 (18)	0.0071 (18)	0.0252 (18)	0.0031 (14)
C24A	0.069 (3)	0.0309 (19)	0.0270 (16)	0.0053 (19)	0.0147 (18)	0.0022 (13)
C25A	0.040 (3)	0.039 (2)	0.0344 (18)	−0.0013 (17)	−0.0007 (15)	0.0037 (14)
C26A	0.025 (2)	0.0370 (19)	0.0373 (17)	−0.0001 (16)	0.0078 (14)	−0.0009 (14)
N24A	0.105 (4)	0.046 (2)	0.0367 (19)	0.026 (2)	0.013 (2)	0.0038 (14)
O41A	0.147 (4)	0.078 (2)	0.0493 (16)	0.046 (2)	0.0538 (19)	0.0176 (14)
O42A	0.122 (4)	0.074 (2)	0.0383 (15)	0.029 (2)	−0.0089 (17)	0.0024 (13)
C11B	0.021 (2)	0.0224 (16)	0.0321 (15)	−0.0033 (14)	0.0061 (13)	−0.0019 (12)
C12B	0.020 (2)	0.0242 (17)	0.0314 (15)	−0.0017 (14)	0.0078 (13)	−0.0018 (12)
C13B	0.031 (2)	0.0231 (16)	0.0313 (16)	0.0000 (15)	0.0069 (14)	−0.0024 (12)
C14B	0.036 (3)	0.0293 (18)	0.0264 (14)	−0.0013 (16)	0.0094 (14)	−0.0019 (13)
C15B	0.027 (2)	0.0301 (18)	0.0376 (17)	−0.0006 (16)	0.0147 (14)	−0.0047 (13)
C16B	0.021 (2)	0.0297 (18)	0.0358 (16)	−0.0017 (15)	0.0049 (13)	−0.0017 (13)
C18B	0.023 (2)	0.0245 (17)	0.0316 (16)	−0.0022 (15)	0.0046 (13)	0.0000 (13)
O11B	0.0338 (17)	0.0349 (13)	0.0341 (11)	0.0106 (11)	0.0126 (10)	0.0023 (9)
O12B	0.0281 (16)	0.0350 (13)	0.0313 (11)	0.0029 (10)	0.0125 (9)	0.0025 (9)
C17B	0.017 (2)	0.0274 (18)	0.0340 (16)	0.0035 (15)	0.0079 (13)	0.0009 (13)
O17B	0.0305 (16)	0.0261 (12)	0.0384 (11)	−0.0017 (11)	0.0129 (10)	0.0027 (9)
N1B	0.0282 (19)	0.0266 (14)	0.0301 (13)	−0.0050 (12)	0.0090 (11)	0.0033 (10)
C21B	0.017 (2)	0.0271 (17)	0.0304 (15)	0.0057 (14)	0.0069 (12)	0.0002 (12)
C22B	0.021 (2)	0.0280 (17)	0.0367 (16)	−0.0010 (15)	0.0091 (13)	−0.0002 (13)
C23B	0.031 (2)	0.0335 (19)	0.0348 (16)	−0.0013 (16)	0.0125 (14)	0.0067 (13)
C24B	0.032 (2)	0.038 (2)	0.0283 (15)	0.0019 (17)	0.0067 (14)	0.0010 (14)
C25B	0.025 (2)	0.0332 (19)	0.0354 (17)	−0.0019 (15)	0.0034 (14)	−0.0037 (13)
C26B	0.020 (2)	0.0308 (19)	0.0360 (16)	0.0005 (15)	0.0078 (13)	0.0060 (13)
N24B	0.045 (2)	0.051 (2)	0.0319 (15)	−0.0044 (16)	0.0061 (13)	−0.0007 (14)
O41B	0.078 (2)	0.0613 (17)	0.0337 (12)	−0.0113 (15)	0.0177 (12)	0.0048 (12)
O42B	0.112 (3)	0.0640 (19)	0.0414 (14)	−0.0305 (18)	0.0095 (14)	−0.0094 (12)

Geometric parameters (Å, º)

C11A—C16A	1.393 (4)	C11B—C16B	1.400 (4)
C11A—C12A	1.403 (4)	C11B—C12B	1.402 (4)
C11A—C17A	1.500 (4)	C11B—C17B	1.499 (4)
C12A—C13A	1.391 (4)	C12B—C13B	1.393 (3)
C12A—C18A	1.481 (4)	C12B—C18B	1.485 (4)
C13A—C14A	1.377 (4)	C13B—C14B	1.383 (4)
C13A—H13A	0.95	C13B—H13B	0.95
C14A—C15A	1.372 (4)	C14B—C15B	1.377 (4)
C14A—H14A	0.95	C14B—H14B	0.95
C15A—C16A	1.377 (4)	C15B—C16B	1.375 (4)
C15A—H15A	0.95	C15B—H15B	0.95
C16A—H16A	0.95	C16B—H16B	0.95
C18A—O11A	1.321 (3)	C18B—O11B	1.324 (3)
C18A—O12A	1.219 (3)	C18B—O12B	1.213 (3)
O11A—H11A	0.84	O11B—H11B	0.84
C17A—O17A	1.231 (3)	C17B—O17B	1.229 (3)
C17A—N1A	1.348 (4)	C17B—N1B	1.353 (4)
N1A—C21A	1.398 (3)	N1B—C21B	1.404 (3)
N1A—H1A	0.88	N1B—H1B	0.88
C21A—C22A	1.389 (4)	C21B—C26B	1.392 (4)
C21A—C26A	1.396 (4)	C21B—C22B	1.396 (4)
C22A—C23A	1.377 (4)	C22B—C23B	1.382 (4)
C22A—H22A	0.95	C22B—H22B	0.95
C23A—C24A	1.381 (5)	C23B—C24B	1.377 (4)
C23A—H23A	0.95	C23B—H23B	0.95
C24A—C25A	1.373 (5)	C24B—C25B	1.373 (4)
C24A—N24A	1.462 (4)	C24B—N24B	1.462 (4)
C25A—C26A	1.376 (4)	C25B—C26B	1.376 (4)
C25A—H25A	0.95	C25B—H25B	0.95
C26A—H26A	0.95	C26B—H26B	0.95
N24A—O42A	1.227 (5)	N24B—O41B	1.220 (3)
N24A—O41A	1.238 (4)	N24B—O42B	1.220 (3)
C16A—C11A—C12A	119.3 (2)	C16B—C11B—C12B	119.3 (2)
C16A—C11A—C17A	118.7 (3)	C16B—C11B—C17B	118.3 (3)
C12A—C11A—C17A	122.0 (3)	C12B—C11B—C17B	122.2 (3)
C13A—C12A—C11A	119.4 (3)	C13B—C12B—C11B	119.7 (3)
C13A—C12A—C18A	121.2 (3)	C13B—C12B—C18B	120.9 (3)
C11A—C12A—C18A	119.2 (2)	C11B—C12B—C18B	119.4 (2)
C14A—C13A—C12A	120.3 (3)	C14B—C13B—C12B	120.1 (3)
C14A—C13A—H13A	119.8	C14B—C13B—H13B	119.9
C12A—C13A—H13A	119.8	C12B—C13B—H13B	119.9
C15A—C14A—C13A	120.3 (3)	C15B—C14B—C13B	120.0 (3)
C15A—C14A—H14A	119.9	C15B—C14B—H14B	120.0
C13A—C14A—H14A	119.9	C13B—C14B—H14B	120.0
C14A—C15A—C16A	120.5 (3)	C16B—C15B—C14B	121.1 (3)
C14A—C15A—H15A	119.7	C16B—C15B—H15B	119.5
C16A—C15A—H15A	119.7	C14B—C15B—H15B	119.5
C15A—C16A—C11A	120.2 (3)	C15B—C16B—C11B	119.8 (3)
C15A—C16A—H16A	119.9	C15B—C16B—H16B	120.1
C11A—C16A—H16A	119.9	C11B—C16B—H16B	120.1
O12A—C18A—O11A	122.9 (3)	O12B—C18B—O11B	123.5 (3)
O12A—C18A—C12A	123.7 (3)	O12B—C18B—C12B	122.8 (3)
O11A—C18A—C12A	113.3 (2)	O11B—C18B—C12B	113.7 (2)
C18A—O11A—H11A	109.5	C18B—O11B—H11B	109.5
O17A—C17A—N1A	124.6 (2)	O17B—C17B—N1B	124.9 (2)
O17A—C17A—C11A	121.0 (3)	O17B—C17B—C11B	120.3 (2)
N1A—C17A—C11A	114.3 (3)	N1B—C17B—C11B	114.7 (2)
C17A—N1A—C21A	127.6 (2)	C17B—N1B—C21B	129.0 (2)
C17A—N1A—H1A	116.2	C17B—N1B—H1B	115.5
C21A—N1A—H1A	116.2	C21B—N1B—H1B	115.5
C22A—C21A—C26A	120.1 (3)	C26B—C21B—C22B	119.4 (2)
C22A—C21A—N1A	122.5 (3)	C26B—C21B—N1B	116.8 (2)
C26A—C21A—N1A	117.3 (3)	C22B—C21B—N1B	123.8 (3)
C23A—C22A—C21A	119.5 (3)	C23B—C22B—C21B	119.6 (3)
C23A—C22A—H22A	120.2	C23B—C22B—H22B	120.2
C21A—C22A—H22A	120.2	C21B—C22B—H22B	120.2
C22A—C23A—C24A	119.2 (3)	C24B—C23B—C22B	119.6 (3)
C22A—C23A—H23A	120.4	C24B—C23B—H23B	120.2
C24A—C23A—H23A	120.4	C22B—C23B—H23B	120.2
C25A—C24A—C23A	122.3 (3)	C25B—C24B—C23B	121.6 (3)
C25A—C24A—N24A	118.3 (4)	C25B—C24B—N24B	119.2 (3)
C23A—C24A—N24A	119.4 (3)	C23B—C24B—N24B	119.2 (3)
C24A—C25A—C26A	118.6 (3)	C24B—C25B—C26B	119.0 (3)
C24A—C25A—H25A	120.7	C24B—C25B—H25B	120.5
C26A—C25A—H25A	120.7	C26B—C25B—H25B	120.5
C25A—C26A—C21A	120.2 (3)	C25B—C26B—C21B	120.7 (3)
C25A—C26A—H26A	119.9	C25B—C26B—H26B	119.7
C21A—C26A—H26A	119.9	C21B—C26B—H26B	119.7
O42A—N24A—O41A	124.0 (3)	O41B—N24B—O42B	122.7 (3)
O42A—N24A—C24A	118.4 (4)	O41B—N24B—C24B	119.3 (3)
O41A—N24A—C24A	117.6 (4)	O42B—N24B—C24B	118.1 (3)
C16A—C11A—C12A—C13A	−2.0 (4)	C16B—C11B—C12B—C13B	0.1 (4)
C17A—C11A—C12A—C13A	−179.2 (3)	C17B—C11B—C12B—C13B	−176.6 (3)
C16A—C11A—C12A—C18A	173.2 (3)	C16B—C11B—C12B—C18B	180.0 (3)
C17A—C11A—C12A—C18A	−4.1 (4)	C17B—C11B—C12B—C18B	3.3 (4)
C11A—C12A—C13A—C14A	0.5 (4)	C11B—C12B—C13B—C14B	−0.9 (4)
C18A—C12A—C13A—C14A	−174.6 (3)	C18B—C12B—C13B—C14B	179.2 (3)
C12A—C13A—C14A—C15A	1.8 (5)	C12B—C13B—C14B—C15B	0.9 (4)
C13A—C14A—C15A—C16A	−2.6 (5)	C13B—C14B—C15B—C16B	0.0 (5)
C14A—C15A—C16A—C11A	1.1 (5)	C14B—C15B—C16B—C11B	−0.8 (4)
C12A—C11A—C16A—C15A	1.2 (5)	C12B—C11B—C16B—C15B	0.7 (4)
C17A—C11A—C16A—C15A	178.6 (3)	C17B—C11B—C16B—C15B	177.5 (3)
C13A—C12A—C18A—O12A	−179.5 (3)	C13B—C12B—C18B—O12B	169.7 (3)
C11A—C12A—C18A—O12A	5.5 (4)	C11B—C12B—C18B—O12B	−10.2 (4)
C13A—C12A—C18A—O11A	2.7 (4)	C13B—C12B—C18B—O11B	−10.5 (4)
C11A—C12A—C18A—O11A	−172.4 (3)	C11B—C12B—C18B—O11B	169.6 (3)
C16A—C11A—C17A—O17A	−79.0 (4)	C16B—C11B—C17B—O17B	−81.3 (4)
C12A—C11A—C17A—O17A	98.3 (4)	C12B—C11B—C17B—O17B	95.4 (3)
C16A—C11A—C17A—N1A	97.4 (3)	C16B—C11B—C17B—N1B	94.6 (3)
C12A—C11A—C17A—N1A	−85.3 (4)	C12B—C11B—C17B—N1B	−88.7 (4)
O17A—C17A—N1A—C21A	−11.3 (5)	O17B—C17B—N1B—C21B	−7.6 (5)
C11A—C17A—N1A—C21A	172.5 (3)	C11B—C17B—N1B—C21B	176.7 (3)
C17A—N1A—C21A—C22A	−26.3 (4)	C17B—N1B—C21B—C26B	−170.5 (3)
C17A—N1A—C21A—C26A	155.2 (3)	C17B—N1B—C21B—C22B	10.8 (5)
C26A—C21A—C22A—C23A	−0.9 (4)	C26B—C21B—C22B—C23B	0.8 (4)
N1A—C21A—C22A—C23A	−179.5 (3)	N1B—C21B—C22B—C23B	179.5 (3)
C21A—C22A—C23A—C24A	0.0 (4)	C21B—C22B—C23B—C24B	0.3 (5)
C22A—C23A—C24A—C25A	0.2 (5)	C22B—C23B—C24B—C25B	−0.9 (5)
C22A—C23A—C24A—N24A	−179.2 (3)	C22B—C23B—C24B—N24B	178.8 (3)
C23A—C24A—C25A—C26A	0.5 (5)	C23B—C24B—C25B—C26B	0.3 (5)
N24A—C24A—C25A—C26A	179.9 (3)	N24B—C24B—C25B—C26B	−179.4 (3)
C24A—C25A—C26A—C21A	−1.4 (4)	C24B—C25B—C26B—C21B	0.8 (5)
C22A—C21A—C26A—C25A	1.6 (4)	C22B—C21B—C26B—C25B	−1.4 (5)
N1A—C21A—C26A—C25A	−179.7 (3)	N1B—C21B—C26B—C25B	179.8 (3)
C25A—C24A—N24A—O42A	−12.5 (5)	C25B—C24B—N24B—O41B	−174.0 (3)
C23A—C24A—N24A—O42A	166.9 (3)	C23B—C24B—N24B—O41B	6.3 (5)
C25A—C24A—N24A—O41A	167.6 (3)	C25B—C24B—N24B—O42B	6.3 (5)
C23A—C24A—N24A—O41A	−13.0 (5)	C23B—C24B—N24B—O42B	−173.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O12B^i	0.88	2.09	2.873 (4)	147
N1B—H1B···O12A^ii	0.88	2.16	2.902 (3)	141
O11A—H11A···O17B	0.84	1.84	2.664 (3)	166
O11B—H11B···O17A^iii	0.84	1.83	2.666 (3)	174
C16A—H16A···O12A^i	0.95	2.46	3.368 (3)	159
C23B—H23B···O41A^iv	0.95	2.45	3.355 (4)	160

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