Structural characterization and theoretical calculations of the monohydrate of the 1:2 cocrystal salt formed from acriflavine and 3,5-di­nitro­benzoic acid

Marczak, M.; Biereg, K.; Zadykowicz, B.; Sikorski, A.

doi:10.1107/S2053229621000681

Structural characterization and theoretical calculations of the monohydrate of the 1:2 cocrystal salt formed from acriflavine and 3,5-dinitrobenzoic acid

M. Marczak, K. Biereg, B. Zadykowicz and A. Sikorski

The synthesis and structural characterization of the monohydrated 1:2 cocrystal salt of acriflavine with 3,5-dinitrobenzoic acid [systematic name: 3,6-diamino-10-methylacridin-10-ium 3,5-dinitrobenzoate–3,5-dinitrobenzoic acid–water (1/1/1), C₁₄H₁₄N₃⁺·C₇H₃N₂O₆⁻·C₇H₄N₂O₆·H₂O] are reported. Single-crystal X-ray diffraction measurements show that the title solvated monohydrate salt crystalizes in the monoclinic space group P2₁ with one acriflavine cation, a 3,5-dinitrobenzoate anion, a 3,5-dinitrobenzoic acid molecule and a water molecule in the asymmetric unit. The neutral and anionic forms of 3,5-dinitrobenzoic acid are linked via O—H

O hydrogen bonds to form a monoanionic dimer. Neighbouring monoanionic dimers of 3,5-dinitrobenzoic acid are linked by nitro–nitro N—O

N and nitro–acid N—O

π intermolecular interactions to produce a porous organic framework. The acriflavine cations are linked with carboxylic acid molecules directly via amine–carboxy N—H

O, amine–nitro N—H

O and acriflavine–carboxy C—H

O hydrogen bonds, and carboxy–acriflavine C—O

π, nitro–acriflavine N—O

π and acriflavine–nitro π–π interactions, or through the water molecule by amino–water N—H

O and water–carboxy O—H

O hydrogen bonds, and are located in the voids of the porous organic framework. The intermolecular interactions were studied using the CrystalExplorer program to provide information about the interaction energies and the dispersion, electrostatic, polarization and repulsion contributions to the lattice energy.

Keywords: acriflavine; 3,5-dinitrobenzoic acid; cocrystal; crystal structure; hydrogen bonding; nitro group interactions; crystal engineering; theoretical calculations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621000681/ef3011sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621000681/ef3011Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621000681/ef3011Isup3.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621000681/ef3011sup4.pdf Additional figures and tables

CCDC reference: 2057462

Computing details top

Data collection: CrysAlis CCD (Rigaku OD, 2015); cell refinement: CrysAlis RED (Rigaku OD, 2015); data reduction: CrysAlis RED (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015) , PLATON (Spek, 2020) and Mercury (Macrae et al., 2020).

3,6-Diamino-10-methylacridin-10-ium 3,5-dinitrobenzoate–3,5-dinitrobenzoic acid–water (1/1/1) top

Crystal data top

C₁₄H₁₄N₃⁺·C₇H₃N₂O₆⁻·C₇H₄N₂O₆·H₂O	F(000) = 688
M_r = 665.53	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.45320 (17) Å	Cell parameters from 18663 reflections
b = 8.26902 (19) Å	θ = 3.5–25.0°
c = 23.1876 (6) Å	µ = 0.13 mm⁻¹
β = 97.362 (2)°	T = 295 K
V = 1417.29 (6) Å³	Plate, red
Z = 2	0.37 × 0.21 × 0.09 mm

Data collection top

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	4966 independent reflections
Radiation source: fine-focus sealed tube	4841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Rigaku OD, 2015)	k = −9→9
T_min = 0.951, T_max = 0.999	l = −27→27
18663 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0454P)² + 0.5024P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.24 e Å⁻³
4966 reflections	Δρ_min = −0.17 e Å⁻³
455 parameters	Absolute structure: Flack x determined using 2143 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
8 restraints	Absolute structure parameter: −0.2 (2)
Primary atom site location: difference Fourier map

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.

Refinement. A good-quality single crystal of the title solvated monohydrate salt was selected for X-ray diffraction data collection at T = 295 (2) K. Diffraction data were collected on the Oxford Diffraction Gemini R ULTRA Ruby CCD diffractometer with the MoKα radiation (λ = 0.71073 Å). The lattice parameters were obtained by least-squares fit to the optimized setting angles of the reflections collected by using the CrysAlis CCD software (Rigaku OD, 2015). Data were reduced using the CrysAlis RED program (Rigaku OD, 2015). The structural determination procedure was carried out using the SHELX package (Sheldrick, 2008). The structure was solved with direct methods and least-squares refinements were carried out based on full-matrix least-squares on F² using the SHELXL2017 program (Sheldrick, 2015).

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1W	−0.2535 (3)	0.0353 (4)	0.34754 (12)	0.0551 (7)
H2W	−0.357 (4)	0.046 (7)	0.3268 (19)	0.083*
H1W	−0.175 (6)	−0.016 (6)	0.326 (2)	0.083*
C1	−0.0056 (4)	0.4592 (5)	0.21829 (15)	0.0431 (9)
H1A	−0.094647	0.469846	0.186540	0.052*
C2	−0.0400 (4)	0.3654 (5)	0.26311 (16)	0.0449 (9)
H2A	−0.149889	0.311245	0.261609	0.054*
C3	0.0934 (5)	0.3494 (4)	0.31315 (15)	0.0407 (8)
C4	0.2590 (4)	0.4273 (4)	0.31307 (14)	0.0371 (7)
H4A	0.346847	0.415927	0.345125	0.045*
C5	0.6678 (4)	0.7653 (4)	0.21974 (13)	0.0349 (7)
H5A	0.756458	0.750124	0.251324	0.042*
C6	0.7060 (5)	0.8619 (4)	0.17362 (13)	0.0383 (7)
C7	0.5686 (5)	0.8829 (5)	0.12475 (14)	0.0405 (8)
H7A	0.591623	0.946237	0.093398	0.049*
C8	0.4066 (5)	0.8109 (4)	0.12438 (13)	0.0402 (8)
H8A	0.319427	0.825608	0.092351	0.048*
C9	0.1977 (5)	0.6385 (4)	0.17188 (14)	0.0409 (8)
H9A	0.108400	0.654003	0.140510	0.049*
N10	0.4611 (3)	0.5960 (3)	0.26557 (11)	0.0342 (6)
C11	0.1604 (4)	0.5423 (4)	0.21744 (14)	0.0380 (8)
C12	0.2966 (4)	0.5207 (4)	0.26699 (13)	0.0331 (7)
C13	0.3637 (4)	0.7126 (4)	0.17135 (14)	0.0359 (7)
C14	0.5012 (4)	0.6915 (4)	0.21976 (12)	0.0329 (7)
N15	0.0558 (4)	0.2637 (4)	0.35971 (14)	0.0497 (8)
H15B	0.134 (5)	0.240 (6)	0.3886 (15)	0.060*
H15A	−0.043 (5)	0.204 (5)	0.3581 (18)	0.060*
C16	0.5969 (5)	0.5778 (6)	0.31678 (14)	0.0484 (9)
H16A	0.547681	0.513918	0.345548	0.073*	0.5
H16B	0.629892	0.682553	0.332578	0.073*	0.5
H16C	0.702102	0.525118	0.305738	0.073*	0.5
H16D	0.705436	0.633808	0.310361	0.073*	0.5
H16E	0.623225	0.465173	0.323331	0.073*	0.5
H16F	0.551015	0.622608	0.350171	0.073*	0.5
N17	0.8669 (4)	0.9336 (5)	0.17349 (13)	0.0467 (7)
H17A	0.943 (5)	0.935 (6)	0.2052 (13)	0.056*
H17B	0.876 (5)	0.985 (5)	0.1368 (13)	0.056*
C18A	1.2087 (4)	0.8050 (4)	0.38422 (12)	0.0242 (6)
C18B	1.3746 (4)	1.2538 (3)	0.14663 (13)	0.0259 (6)
C19A	1.3690 (4)	0.8206 (3)	0.42196 (13)	0.0258 (6)
H19A	1.468498	0.873246	0.410208	0.031*
C19B	1.2071 (4)	1.2393 (4)	0.11330 (14)	0.0324 (7)
H19B	1.116807	1.176785	0.126405	0.039*
C20A	1.3770 (4)	0.7562 (3)	0.47729 (13)	0.0262 (6)
C20B	1.1758 (4)	1.3172 (4)	0.06128 (14)	0.0345 (7)
C21A	1.2340 (4)	0.6786 (3)	0.49754 (12)	0.0259 (6)
H21A	1.241106	0.639468	0.535361	0.031*
C21B	1.3064 (4)	1.4110 (4)	0.03919 (13)	0.0344 (7)
H21B	1.282852	1.463916	0.003634	0.041*
C22A	1.0796 (4)	0.6626 (3)	0.45828 (12)	0.0258 (6)
C22B	1.4723 (4)	1.4212 (3)	0.07285 (13)	0.0282 (6)
C23A	1.0636 (4)	0.7230 (3)	0.40247 (12)	0.0250 (6)
H23A	0.957047	0.709024	0.377368	0.030*
C23B	1.5091 (4)	1.3456 (3)	0.12620 (12)	0.0256 (6)
H23B	1.622172	1.356047	0.148063	0.031*
C24A	1.1888 (4)	0.8800 (4)	0.32463 (12)	0.0269 (6)
C24B	1.4120 (4)	1.1718 (4)	0.20526 (12)	0.0286 (6)
O25A	1.3325 (3)	0.9413 (3)	0.30974 (9)	0.0356 (5)
O25B	1.2778 (3)	1.0829 (3)	0.21672 (9)	0.0343 (5)
H25B	1.306 (5)	1.027 (5)	0.2543 (10)	0.051*
O26A	1.0381 (3)	0.8785 (3)	0.29518 (9)	0.0354 (5)
O26B	1.5540 (3)	1.1933 (3)	0.23619 (9)	0.0355 (5)
N27A	1.5451 (3)	0.7739 (3)	0.51778 (12)	0.0342 (6)
N27B	0.9995 (4)	1.2977 (4)	0.02541 (16)	0.0526 (8)
O28A	1.6731 (3)	0.8425 (3)	0.50034 (12)	0.0479 (6)
O28B	0.8841 (4)	1.2178 (4)	0.04580 (15)	0.0679 (9)
O29A	1.5499 (3)	0.7162 (3)	0.56674 (10)	0.0477 (6)
O29B	0.9773 (4)	1.3628 (5)	−0.02219 (14)	0.0782 (10)
N30A	0.9241 (3)	0.5778 (3)	0.47753 (11)	0.0320 (6)
N30B	1.6155 (4)	1.5175 (3)	0.05112 (11)	0.0343 (6)
O31A	0.7969 (3)	0.5423 (3)	0.44079 (10)	0.0443 (6)
O31B	1.7573 (3)	1.5373 (3)	0.08294 (10)	0.0415 (5)
O32A	0.9292 (3)	0.5482 (3)	0.52926 (9)	0.0410 (6)
O32B	1.5837 (4)	1.5724 (3)	0.00180 (10)	0.0521 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0384 (13)	0.0737 (19)	0.0508 (15)	0.0081 (14)	−0.0034 (11)	−0.0028 (15)
C1	0.0385 (18)	0.047 (2)	0.0392 (19)	0.0128 (16)	−0.0127 (14)	−0.0126 (16)
C2	0.0307 (17)	0.049 (2)	0.053 (2)	0.0052 (15)	−0.0024 (14)	−0.0178 (18)
C3	0.0398 (18)	0.0398 (19)	0.0413 (19)	0.0117 (15)	0.0004 (14)	−0.0094 (15)
C4	0.0282 (15)	0.0399 (18)	0.0406 (18)	0.0083 (13)	−0.0051 (13)	−0.0132 (15)
C5	0.0352 (16)	0.0393 (18)	0.0269 (15)	0.0098 (14)	−0.0087 (12)	−0.0097 (13)
C6	0.0490 (19)	0.0396 (17)	0.0253 (15)	0.0139 (15)	0.0012 (13)	−0.0048 (13)
C7	0.0479 (19)	0.0437 (19)	0.0283 (16)	0.0139 (16)	−0.0005 (13)	−0.0024 (14)
C8	0.052 (2)	0.0397 (18)	0.0250 (16)	0.0208 (16)	−0.0086 (13)	−0.0082 (14)
C9	0.0449 (19)	0.0406 (18)	0.0324 (17)	0.0179 (15)	−0.0133 (14)	−0.0136 (14)
N10	0.0299 (13)	0.0347 (14)	0.0347 (14)	0.0026 (11)	−0.0088 (10)	−0.0095 (11)
C11	0.0298 (15)	0.0391 (18)	0.0419 (18)	0.0092 (14)	−0.0075 (12)	−0.0187 (15)
C12	0.0357 (16)	0.0286 (15)	0.0326 (15)	0.0116 (13)	−0.0048 (12)	−0.0132 (13)
C13	0.0340 (16)	0.0358 (17)	0.0341 (16)	0.0079 (14)	−0.0108 (13)	−0.0144 (14)
C14	0.0438 (17)	0.0278 (15)	0.0244 (14)	0.0123 (14)	−0.0055 (12)	−0.0093 (13)
N15	0.0369 (16)	0.061 (2)	0.0487 (19)	−0.0013 (15)	−0.0037 (13)	−0.0035 (17)
C16	0.0383 (17)	0.069 (3)	0.0336 (17)	−0.0040 (18)	−0.0101 (14)	0.0078 (18)
N17	0.0392 (16)	0.065 (2)	0.0339 (15)	0.0013 (15)	−0.0017 (12)	0.0031 (15)
C18A	0.0265 (13)	0.0211 (13)	0.0251 (14)	0.0027 (11)	0.0038 (11)	−0.0050 (11)
C18B	0.0228 (13)	0.0240 (14)	0.0318 (15)	0.0012 (11)	0.0072 (11)	−0.0056 (12)
C19A	0.0239 (13)	0.0184 (13)	0.0358 (16)	0.0010 (11)	0.0070 (11)	−0.0058 (12)
C19B	0.0259 (14)	0.0277 (15)	0.0435 (18)	−0.0007 (12)	0.0040 (12)	−0.0090 (13)
C20A	0.0238 (13)	0.0206 (13)	0.0322 (15)	0.0032 (11)	−0.0038 (11)	−0.0043 (11)
C20B	0.0289 (15)	0.0313 (16)	0.0407 (18)	0.0013 (13)	−0.0059 (13)	−0.0125 (14)
C21A	0.0280 (14)	0.0198 (13)	0.0288 (14)	0.0018 (11)	−0.0006 (11)	0.0021 (11)
C21B	0.0446 (18)	0.0307 (17)	0.0255 (15)	0.0087 (14)	−0.0049 (12)	−0.0071 (13)
C22A	0.0259 (14)	0.0230 (14)	0.0279 (14)	−0.0027 (11)	0.0012 (11)	−0.0008 (12)
C22B	0.0337 (15)	0.0205 (13)	0.0313 (15)	−0.0008 (12)	0.0074 (12)	−0.0038 (12)
C23A	0.0238 (13)	0.0238 (14)	0.0265 (14)	−0.0021 (11)	−0.0008 (10)	−0.0044 (11)
C23B	0.0246 (13)	0.0251 (14)	0.0268 (15)	0.0002 (11)	0.0024 (11)	−0.0039 (11)
C24A	0.0275 (14)	0.0251 (14)	0.0289 (15)	0.0008 (12)	0.0065 (11)	−0.0042 (12)
C24B	0.0280 (15)	0.0262 (15)	0.0326 (15)	0.0021 (12)	0.0082 (12)	−0.0028 (13)
O25A	0.0301 (11)	0.0431 (13)	0.0353 (12)	−0.0024 (10)	0.0103 (9)	0.0053 (10)
O25B	0.0327 (11)	0.0368 (12)	0.0349 (11)	−0.0065 (9)	0.0105 (9)	0.0020 (10)
O26A	0.0355 (11)	0.0457 (13)	0.0240 (11)	−0.0075 (10)	0.0008 (9)	0.0026 (10)
O26B	0.0294 (11)	0.0399 (12)	0.0365 (11)	0.0001 (10)	0.0016 (9)	0.0072 (10)
N27A	0.0255 (13)	0.0258 (14)	0.0482 (17)	0.0000 (11)	−0.0072 (11)	0.0017 (12)
N27B	0.0399 (17)	0.0503 (19)	0.061 (2)	0.0045 (16)	−0.0184 (15)	−0.0167 (17)
O28A	0.0300 (12)	0.0360 (13)	0.0727 (17)	−0.0079 (10)	−0.0124 (11)	0.0159 (12)
O28B	0.0349 (14)	0.0521 (17)	0.108 (2)	−0.0079 (13)	−0.0231 (14)	−0.0174 (17)
O29A	0.0416 (13)	0.0550 (16)	0.0416 (13)	−0.0040 (12)	−0.0128 (10)	0.0084 (12)
O29B	0.0598 (19)	0.103 (3)	0.061 (2)	0.0028 (19)	−0.0344 (15)	−0.0045 (19)
N30A	0.0283 (12)	0.0344 (14)	0.0319 (13)	−0.0063 (11)	−0.0012 (10)	0.0049 (11)
N30B	0.0491 (16)	0.0276 (13)	0.0271 (13)	−0.0016 (12)	0.0086 (11)	0.0012 (11)
O31A	0.0350 (11)	0.0602 (16)	0.0351 (11)	−0.0211 (12)	−0.0060 (9)	0.0108 (11)
O31B	0.0402 (12)	0.0443 (13)	0.0395 (12)	−0.0105 (11)	0.0035 (10)	0.0013 (11)
O32A	0.0402 (12)	0.0499 (15)	0.0318 (12)	−0.0114 (11)	0.0003 (9)	0.0167 (11)
O32B	0.0734 (17)	0.0488 (15)	0.0332 (13)	−0.0121 (13)	0.0030 (11)	0.0110 (11)

Geometric parameters (Å, º) top

O1W—H2W	0.86 (3)	C18A—C23A	1.387 (4)
O1W—H1W	0.91 (3)	C18A—C19A	1.394 (4)
C1—C2	1.347 (6)	C18A—C24A	1.504 (4)
C1—C11	1.418 (5)	C18B—C19B	1.387 (4)
C1—H1A	0.9300	C18B—C23B	1.388 (4)
C2—C3	1.434 (5)	C18B—C24B	1.513 (4)
C2—H2A	0.9300	C19A—C20A	1.383 (4)
C3—N15	1.350 (5)	C19A—H19A	0.9300
C3—C4	1.393 (5)	C19B—C20B	1.361 (5)
C4—C12	1.376 (5)	C19B—H19B	0.9300
C4—H4A	0.9300	C20A—C21A	1.377 (4)
C5—C14	1.383 (5)	C20A—N27A	1.474 (4)
C5—C6	1.393 (5)	C20B—C21B	1.392 (5)
C5—H5A	0.9300	C20B—N27B	1.471 (4)
C6—N17	1.338 (5)	C21A—C22A	1.379 (4)
C6—C7	1.437 (5)	C21A—H21A	0.9300
C7—C8	1.345 (5)	C21B—C22B	1.378 (4)
C7—H7A	0.9300	C21B—H21B	0.9300
C8—C13	1.428 (5)	C22A—C23A	1.378 (4)
C8—H8A	0.9300	C22A—N30A	1.471 (4)
C9—C11	1.379 (5)	C22B—C23B	1.382 (4)
C9—C13	1.382 (5)	C22B—N30B	1.471 (4)
C9—H9A	0.9300	C23A—H23A	0.9300
N10—C12	1.379 (4)	C23B—H23B	0.9300
N10—C14	1.387 (4)	C24A—O26A	1.238 (3)
N10—C16	1.466 (4)	C24A—O25A	1.272 (3)
C11—C12	1.444 (4)	C24B—O26B	1.213 (4)
C13—C14	1.430 (4)	C24B—O25B	1.296 (4)
N15—H15B	0.85 (3)	O25B—H25B	0.987 (14)
N15—H15A	0.88 (3)	N27A—O28A	1.222 (4)
C16—H16A	0.9600	N27A—O29A	1.228 (4)
C16—H16B	0.9600	N27B—O29B	1.220 (4)
C16—H16C	0.9600	N27B—O28B	1.227 (5)
C16—H16D	0.9600	N30A—O32A	1.220 (3)
C16—H16E	0.9600	N30A—O31A	1.226 (3)
C16—H16F	0.9600	N30B—O31B	1.220 (3)
N17—H17A	0.87 (2)	N30B—O32B	1.225 (3)
N17—H17B	0.96 (2)

H2W—O1W—H1W	110 (5)	H16B—C16—H16F	56.3
C2—C1—C11	122.9 (3)	H16C—C16—H16F	141.1
C2—C1—H1A	118.6	H16D—C16—H16F	109.5
C11—C1—H1A	118.6	H16E—C16—H16F	109.5
C1—C2—C3	119.8 (3)	C6—N17—H17A	120 (3)
C1—C2—H2A	120.1	C6—N17—H17B	111 (2)
C3—C2—H2A	120.1	H17A—N17—H17B	129 (4)
N15—C3—C4	121.2 (3)	C23A—C18A—C19A	119.5 (3)
N15—C3—C2	120.1 (3)	C23A—C18A—C24A	119.5 (2)
C4—C3—C2	118.6 (3)	C19A—C18A—C24A	120.9 (2)
C12—C4—C3	122.0 (3)	C19B—C18B—C23B	119.7 (3)
C12—C4—H4A	119.0	C19B—C18B—C24B	120.7 (3)
C3—C4—H4A	119.0	C23B—C18B—C24B	119.6 (3)
C14—C5—C6	121.7 (3)	C20A—C19A—C18A	118.6 (3)
C14—C5—H5A	119.2	C20A—C19A—H19A	120.7
C6—C5—H5A	119.2	C18A—C19A—H19A	120.7
N17—C6—C5	121.8 (3)	C20B—C19B—C18B	119.5 (3)
N17—C6—C7	119.5 (3)	C20B—C19B—H19B	120.2
C5—C6—C7	118.6 (3)	C18B—C19B—H19B	120.2
C8—C7—C6	120.0 (3)	C21A—C20A—C19A	123.5 (3)
C8—C7—H7A	120.0	C21A—C20A—N27A	117.4 (3)
C6—C7—H7A	120.0	C19A—C20A—N27A	119.0 (3)
C7—C8—C13	122.4 (3)	C19B—C20B—C21B	122.8 (3)
C7—C8—H8A	118.8	C19B—C20B—N27B	119.2 (3)
C13—C8—H8A	118.8	C21B—C20B—N27B	117.9 (3)
C11—C9—C13	122.1 (3)	C20A—C21A—C22A	115.9 (3)
C11—C9—H9A	118.9	C20A—C21A—H21A	122.1
C13—C9—H9A	118.9	C22A—C21A—H21A	122.1
C12—N10—C14	123.7 (3)	C22B—C21B—C20B	116.4 (3)
C12—N10—C16	117.3 (3)	C22B—C21B—H21B	121.8
C14—N10—C16	119.0 (3)	C20B—C21B—H21B	121.8
C9—C11—C1	123.6 (3)	C23A—C22A—C21A	123.3 (3)
C9—C11—C12	119.4 (3)	C23A—C22A—N30A	118.8 (2)
C1—C11—C12	117.1 (3)	C21A—C22A—N30A	117.9 (2)
C4—C12—N10	122.8 (3)	C21B—C22B—C23B	122.7 (3)
C4—C12—C11	119.7 (3)	C21B—C22B—N30B	118.5 (3)
N10—C12—C11	117.5 (3)	C23B—C22B—N30B	118.8 (3)
C9—C13—C8	123.2 (3)	C22A—C23A—C18A	119.1 (2)
C9—C13—C14	119.4 (3)	C22A—C23A—H23A	120.4
C8—C13—C14	117.4 (3)	C18A—C23A—H23A	120.4
C5—C14—N10	122.2 (3)	C22B—C23B—C18B	118.9 (3)
C5—C14—C13	119.9 (3)	C22B—C23B—H23B	120.5
N10—C14—C13	117.8 (3)	C18B—C23B—H23B	120.5
C3—N15—H15B	124 (3)	O26A—C24A—O25A	126.2 (3)
C3—N15—H15A	121 (3)	O26A—C24A—C18A	118.5 (2)
H15B—N15—H15A	113 (4)	O25A—C24A—C18A	115.3 (2)
N10—C16—H16A	109.5	O26B—C24B—O25B	126.9 (3)
N10—C16—H16B	109.5	O26B—C24B—C18B	120.8 (3)
H16A—C16—H16B	109.5	O25B—C24B—C18B	112.4 (2)
N10—C16—H16C	109.5	C24A—O25A—H25B	114.1 (15)
H16A—C16—H16C	109.5	C24B—O25B—H25B	112 (2)
H16B—C16—H16C	109.5	O28A—N27A—O29A	123.7 (3)
N10—C16—H16D	109.5	O28A—N27A—C20A	118.1 (3)
H16A—C16—H16D	141.1	O29A—N27A—C20A	118.2 (3)
H16B—C16—H16D	56.3	O29B—N27B—O28B	124.4 (3)
H16C—C16—H16D	56.3	O29B—N27B—C20B	118.1 (3)
N10—C16—H16E	109.5	O28B—N27B—C20B	117.4 (3)
H16A—C16—H16E	56.3	O32A—N30A—O31A	124.0 (2)
H16B—C16—H16E	141.1	O32A—N30A—C22A	117.9 (2)
H16C—C16—H16E	56.3	O31A—N30A—C22A	118.2 (2)
H16D—C16—H16E	109.5	O31B—N30B—O32B	124.3 (3)
N10—C16—H16F	109.5	O31B—N30B—C22B	118.4 (2)
H16A—C16—H16F	56.3	O32B—N30B—C22B	117.3 (3)

C11—C1—C2—C3	1.2 (5)	C18A—C19A—C20A—N27A	−179.2 (2)
C1—C2—C3—N15	176.0 (3)	C18B—C19B—C20B—C21B	0.7 (5)
C1—C2—C3—C4	−2.3 (5)	C18B—C19B—C20B—N27B	178.4 (3)
N15—C3—C4—C12	−177.2 (3)	C19A—C20A—C21A—C22A	2.2 (4)
C2—C3—C4—C12	1.1 (5)	N27A—C20A—C21A—C22A	−179.3 (2)
C14—C5—C6—N17	179.9 (3)	C19B—C20B—C21B—C22B	0.3 (5)
C14—C5—C6—C7	−0.7 (5)	N27B—C20B—C21B—C22B	−177.4 (3)
N17—C6—C7—C8	179.8 (3)	C20A—C21A—C22A—C23A	−1.7 (4)
C5—C6—C7—C8	0.4 (5)	C20A—C21A—C22A—N30A	178.9 (3)
C6—C7—C8—C13	0.1 (5)	C20B—C21B—C22B—C23B	−1.0 (4)
C13—C9—C11—C1	−177.3 (3)	C20B—C21B—C22B—N30B	179.4 (3)
C13—C9—C11—C12	1.5 (5)	C21A—C22A—C23A—C18A	−0.3 (4)
C2—C1—C11—C9	179.9 (3)	N30A—C22A—C23A—C18A	179.1 (2)
C2—C1—C11—C12	1.1 (5)	C19A—C18A—C23A—C22A	1.8 (4)
C3—C4—C12—N10	−178.6 (3)	C24A—C18A—C23A—C22A	−176.4 (3)
C3—C4—C12—C11	1.3 (4)	C21B—C22B—C23B—C18B	0.8 (4)
C14—N10—C12—C4	−179.5 (3)	N30B—C22B—C23B—C18B	−179.6 (2)
C16—N10—C12—C4	−2.0 (4)	C19B—C18B—C23B—C22B	0.2 (4)
C14—N10—C12—C11	0.6 (4)	C24B—C18B—C23B—C22B	−179.3 (2)
C16—N10—C12—C11	178.1 (3)	C23A—C18A—C24A—O26A	6.1 (4)
C9—C11—C12—C4	178.8 (3)	C19A—C18A—C24A—O26A	−172.1 (3)
C1—C11—C12—C4	−2.4 (4)	C23A—C18A—C24A—O25A	−174.6 (3)
C9—C11—C12—N10	−1.3 (4)	C19A—C18A—C24A—O25A	7.2 (4)
C1—C11—C12—N10	177.5 (3)	C19B—C18B—C24B—O26B	−174.9 (3)
C11—C9—C13—C8	179.1 (3)	C23B—C18B—C24B—O26B	4.5 (4)
C11—C9—C13—C14	−0.9 (5)	C19B—C18B—C24B—O25B	4.5 (4)
C7—C8—C13—C9	179.6 (3)	C23B—C18B—C24B—O25B	−176.1 (2)
C7—C8—C13—C14	−0.4 (5)	C21A—C20A—N27A—O28A	180.0 (3)
C6—C5—C14—N10	−179.6 (3)	C19A—C20A—N27A—O28A	−1.5 (4)
C6—C5—C14—C13	0.4 (4)	C21A—C20A—N27A—O29A	1.3 (4)
C12—N10—C14—C5	180.0 (3)	C19A—C20A—N27A—O29A	179.9 (3)
C16—N10—C14—C5	2.5 (4)	C19B—C20B—N27B—O29B	−176.8 (3)
C12—N10—C14—C13	0.0 (4)	C21B—C20B—N27B—O29B	1.0 (5)
C16—N10—C14—C13	−177.5 (3)	C19B—C20B—N27B—O28B	3.8 (5)
C9—C13—C14—C5	−179.9 (3)	C21B—C20B—N27B—O28B	−178.5 (3)
C8—C13—C14—C5	0.1 (4)	C23A—C22A—N30A—O32A	−168.4 (3)
C9—C13—C14—N10	0.1 (4)	C21A—C22A—N30A—O32A	11.0 (4)
C8—C13—C14—N10	−179.9 (3)	C23A—C22A—N30A—O31A	11.1 (4)
C23A—C18A—C19A—C20A	−1.3 (4)	C21A—C22A—N30A—O31A	−169.5 (3)
C24A—C18A—C19A—C20A	176.8 (3)	C21B—C22B—N30B—O31B	174.1 (3)
C23B—C18B—C19B—C20B	−0.9 (4)	C23B—C22B—N30B—O31B	−5.5 (4)
C24B—C18B—C19B—C20B	178.6 (3)	C21B—C22B—N30B—O32B	−6.0 (4)
C18A—C19A—C20A—C21A	−0.8 (4)	C23B—C22B—N30B—O32B	174.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O26Aⁱ	0.92 (5)	2.02 (5)	2.925 (4)	167 (4)
O1W—H2W···O25Aⁱⁱ	0.86 (4)	2.46 (4)	3.194 (5)	144 (5)
O1W—H2W···O26Bⁱⁱ	0.86 (4)	2.45 (5)	3.079 (4)	131 (4)
N15—H15A···O1W	0.88 (4)	2.09 (4)	2.966 (4)	171 (4)
N15—H15B···O29Aⁱⁱⁱ	0.85 (4)	2.46 (4)	3.227 (3)	151 (3)
N15—H15B···O32A^iv	0.85 (4)	2.57 (4)	3.121 (3)	124 (3)
N17—H17A···O26A	0.87 (3)	2.17 (4)	2.979 (4)	155 (4)
O25B—H25B···O25A	0.99 (3)	1.46 (3)	2.442 (4)	176 (4)
C2—H2A···O26Bⁱⁱ	0.93	2.42	3.330 (4)	167
C5—H5A···O26A	0.93	2.45	3.212 (4)	139

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

The geometry (Å, °) of the interactions involving the nitro groups and π–π interactions in the crystal of the title solvated monohydrate salt top

Y—X···A	X···A	Y—X···A
N30A—O31A···N27A^vii	3.352 (3)	85.9 (2)
N27A—O28A···N30A^viii	2.971 (3)	104.7 (2)
N30B—O31B···N27B^viii	3.095 (4)	99.3 (3)
N27B—O28B···N30B^vii	3.198 (4)	94.1 (3)
N30A—O32A···Cg4Aⁱⁱⁱ	2.903 (3)	116.8 (2)
N30B—O32B···Cg4B^v	3.174 (3)	150.2 (2)
C22A—O25A···Cg1^viii	3.410 (3)	85.2 (2)
N30B—O31B···Cg3^vi	3.490 (3)	90.0 (2)
Cg1···Cg4B^vi	3.758 (2)	1.4 (1)^a

Note: (a) dihedral angle between the mean planes of the aromatic rings. Cg1, Cg, Cg4A and Cg4B denote the ring centroids (see Fig. 2).

Symmetry codes: (iii) -x+2, y-1/2, -z; (vi) -x+3, y+1/2, -z; (vii) x+1, y+1, z; (viii) x-1, y, z; (ix) x+1, y, z.

The values of interaction energies (kJ mol^-1) for pairs of adjacent molecules in the title solvated monohydrate salt top

Pair	Interaction	E_tot	E_ele	E_pol	E_dis	E_rep
1	(N15—H15A···O1W)	-7.0	0.0	-9.5	0.0	0.0
2	(N17—H17A···O26A)	-30.1	0.0	-40.7	0.0	0.0
3	(O1W—H2W···O26B)	-38.9	0.0	-52.6	0.0	0.0
4a	(N27A—O28A···N30A)*	-6.5	0.0	-8.8	0.0	0.0
4b	(N30B—O31B···N27B)*	-14.2	-7.0	-1.2	-10.9	5.8
5a	(N30A—O32A···Cg4A)	-8.7	0.0	-11.7	0.0	0.0
5b	(N30B—O32B···Cg4B)	-12.4	-6.1	-1.6	-11.6	8.7
6a	(C22A—O25A···Cg1)	-28.4	0.0	-38.3	0.0	0.0
6b	(N30B—O31B···Cg3)*	-6.3	0.0	-8.5	0.0	0.0
7a	(N15—H15A···O32A)	-6.3	0.0	-8.5	0.0	0.0
7b	(N15—H15A···O29A)	-10.0	0.0	-13.5	0.0	0.0
8a	(O1W—H1W···O26A)	-9.7	0.0	-13.1	0.0	0.0
8b	(O1W—H2W···O25A)	-5.4	0.0	-7.3	0.0	0.0

Note: (*) the shortest contacts identified among respective pair of molecules.

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Structural characterization and theoretical calculations of the monohydrate of the 1:2 cocrystal salt formed from acriflavine and 3,5-di­nitro­benzoic acid

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Structural characterization and theoretical calculations of the monohydrate of the 1:2 cocrystal salt formed from acriflavine and 3,5-dinitrobenzoic acid