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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), C
14H
14N
3+·C
7H
3N
2O
6−·C
7H
4N
2O
6·H
2O] are reported. Single-crystal X-ray diffraction measurements show that the title solvated monohydrate salt crystalizes in the monoclinic space group
P2
1 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.
Supporting information
CCDC reference: 2057462
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 |
Mr = 665.53 | Dx = 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 | Rint = 0.026 |
Detector resolution: 10.4002 pixels mm-1 | θmax = 25.0°, θmin = 3.5° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis RED; Rigaku OD, 2015) | k = −9→9 |
Tmin = 0.951, Tmax = 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(Fo2) + (0.0454P)2 + 0.5024P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.24 e Å−3 |
4966 reflections | Δρmin = −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 | Uiso*/Ueq | 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···O32Aiv | 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 topY—X···A | X···A | Y—X···A |
N30A—O31A···N27Avii | 3.352 (3) | 85.9 (2) |
N27A—O28A···N30Aviii | 2.971 (3) | 104.7 (2) |
N30B—O31B···N27Bviii | 3.095 (4) | 99.3 (3) |
N27B—O28B···N30Bvii | 3.198 (4) | 94.1 (3) |
N30A—O32A···Cg4Aiii | 2.903 (3) | 116.8 (2) |
N30B—O32B···Cg4Bv | 3.174 (3) | 150.2 (2) |
C22A—O25A···Cg1viii | 3.410 (3) | 85.2 (2) |
N30B—O31B···Cg3vi | 3.490 (3) | 90.0 (2) |
Cg1···Cg4Bvi | 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 topPair | Interaction | Etot | Eele | Epol | Edis | Erep |
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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