Download citation
Download citation
link to html
The inter­molecular inter­actions and salt formation of acridine with 4-amino­salicylic acid, 5-chloro­salicylic acid and hippuric acid were investigated. The salts obtained were acridin-1-ium 4-amino­salicylate (4-amino-2-hy­droxy­benzoate), C13H10N+·C7H6NO3 (I), acridin-1-ium 5-chloro­salicylate (5-chloro-2-hy­droxy­benzoate), C13H10N+·C7H4ClO3 (II), and acridin-1-ium hippurate (2-benz­amido­acetate) monohydrate, C13H10N+·C9H8NO3·H2O (III). Acridine is involved in strong inter­molecular inter­actions with the hy­droxy group of the three acids, enabling it to form supra­molecular assemblies. Hirshfeld surfaces, fingerprint plots and enrichment ratios were generated and investigated, and the inter­molecular inter­actions were analyzed, revealing their qu­anti­tative con­tri­butions in the crystal packing of salts I, II and III. A quantum theory of atoms in mol­ecules (QTAIM) analysis shows the charge–density distribution of the inter­molecular inter­actions. The isosurfaces of the noncovalent inter­actions were studied, which allows visualization of where the hydrogen-bonding and dispersion inter­actions con­tri­bute within the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621011189/ef3021sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011189/ef3021Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011189/ef3021IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011189/ef3021IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011189/ef3021Isup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011189/ef3021IIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011189/ef3021IIIsup7.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621011189/ef3021sup8.pdf
Supplementary material

CCDC references: 2048258; 2084162; 2084161

Computing details top

For all structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015). Program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a) for (I); SHELXS97 (Sheldrick, 2008) for (II); SHELXT2018 (Sheldrick, 2015a) for (III). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for (I); SHELXL2018 (Sheldrick, 2015b) for (II), (III). For all structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020). Software used to prepare material for publication: WinGX (Farrugia, 2012) for (I); OLEX2 (Dolomanov et al., 2009) for (II), (III).

Acridin-1-ium 4-amino-2-hydroxybenzoate (I) top
Crystal data top
C13H10N+·C7H6NO3F(000) = 696
Mr = 332.35Dx = 1.263 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 20496 reflections
a = 7.1209 (5) Åθ = 2.6–28.3°
b = 12.1988 (12) ŵ = 0.09 mm1
c = 20.1202 (18) ÅT = 293 K
V = 1747.8 (3) Å3Block, brown
Z = 40.88 × 0.50 × 0.23 mm
Data collection top
Bruker D8 QUEST ECO
diffractometer
3934 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω and phi scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 96
Tmin = 0.949, Tmax = 0.981k = 1616
20496 measured reflectionsl = 2626
4274 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0765P)2 + 0.0658P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
4274 reflectionsΔρmax = 0.19 e Å3
290 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack (1983)
0 constraintsAbsolute structure parameter: 0.0 (9)
Primary atom site location: structure-invariant direct methods
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Diagrams and publication material were generated using PLATON (Spek, 2020), OLEX2 (Dolomanov et al., 2009) and Mercury software (Macrae et al., 2020).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.62266 (13)0.74164 (9)0.29886 (6)0.0559 (3)
O20.51812 (15)0.57511 (9)0.36654 (5)0.0552 (3)
O10.22130 (16)0.51923 (8)0.36038 (6)0.0590 (3)
N20.1561 (2)0.96426 (10)0.19765 (8)0.0610 (3)
N10.26192 (16)0.37488 (9)0.45353 (5)0.0442 (2)
C150.29836 (16)0.69110 (9)0.31332 (6)0.0367 (2)
C140.34981 (18)0.58939 (10)0.34906 (6)0.0421 (3)
C180.20294 (17)0.87705 (9)0.23705 (6)0.0417 (2)
C160.43767 (16)0.76183 (10)0.28820 (6)0.0395 (3)
C200.11121 (16)0.71904 (10)0.30111 (6)0.0414 (3)
C190.06189 (17)0.80983 (11)0.26471 (7)0.0437 (3)
C170.39049 (17)0.85247 (10)0.25015 (7)0.0443 (3)
C70.2536 (2)0.22836 (11)0.55772 (6)0.0501 (3)
C60.2548 (2)0.18865 (10)0.49289 (6)0.0460 (3)
C10.25990 (17)0.26626 (10)0.43989 (6)0.0425 (3)
C20.2618 (2)0.22936 (13)0.37333 (7)0.0540 (3)
C80.25627 (19)0.34026 (11)0.57105 (6)0.0465 (3)
C90.26015 (19)0.41456 (11)0.51636 (6)0.0451 (3)
C50.2516 (3)0.07505 (12)0.47674 (9)0.0615 (4)
C130.2540 (2)0.38421 (15)0.63666 (7)0.0605 (4)
C30.2577 (3)0.12005 (15)0.36041 (8)0.0660 (4)
C40.2527 (3)0.04228 (15)0.41247 (10)0.0700 (4)
C100.2624 (3)0.52876 (13)0.52776 (8)0.0624 (4)
C120.2562 (3)0.49381 (18)0.64618 (9)0.0726 (5)
C110.2594 (3)0.56670 (16)0.59123 (10)0.0753 (5)
H100.258 (3)0.5774 (17)0.4891 (10)0.075 (6)*
H200.016 (3)0.6723 (16)0.3195 (9)0.065 (5)*
H2B0.245 (3)0.9962 (16)0.1749 (9)0.063 (5)*
H1A0.256 (3)0.4329 (15)0.4155 (9)0.065 (5)*
H130.247 (3)0.3311 (17)0.6764 (11)0.075 (6)*
H50.247 (3)0.0230 (17)0.5138 (9)0.074 (6)*
H20.260 (3)0.2835 (14)0.3402 (9)0.058 (5)*
H70.246 (3)0.1771 (16)0.5939 (10)0.067 (5)*
H30.260 (3)0.0930 (16)0.3120 (10)0.071 (6)*
H120.252 (4)0.526 (2)0.6973 (11)0.094 (7)*
H2A0.021 (3)0.9765 (18)0.1899 (10)0.073 (6)*
H190.073 (2)0.8282 (13)0.2554 (8)0.049 (4)*
H170.493 (3)0.8951 (15)0.2308 (9)0.059 (5)*
H160.615 (3)0.685 (2)0.3293 (11)0.074 (6)*
H40.257 (4)0.0347 (19)0.3991 (10)0.087 (7)*
H110.272 (3)0.648 (2)0.5982 (12)0.096 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0332 (4)0.0517 (5)0.0828 (7)0.0016 (4)0.0030 (4)0.0075 (5)
O20.0490 (5)0.0532 (5)0.0635 (6)0.0071 (4)0.0071 (4)0.0059 (4)
O10.0595 (6)0.0517 (5)0.0656 (6)0.0103 (5)0.0126 (5)0.0221 (5)
N20.0501 (7)0.0453 (6)0.0874 (9)0.0001 (5)0.0023 (6)0.0227 (6)
N10.0458 (5)0.0441 (5)0.0425 (5)0.0008 (4)0.0020 (4)0.0051 (4)
C150.0367 (5)0.0345 (5)0.0390 (5)0.0016 (4)0.0014 (4)0.0034 (4)
C140.0461 (6)0.0404 (6)0.0397 (5)0.0007 (5)0.0007 (4)0.0004 (4)
C180.0424 (6)0.0312 (5)0.0515 (6)0.0005 (4)0.0007 (5)0.0018 (4)
C160.0334 (5)0.0369 (5)0.0483 (6)0.0015 (4)0.0000 (4)0.0052 (5)
C200.0347 (5)0.0405 (6)0.0489 (6)0.0026 (4)0.0043 (5)0.0008 (5)
C190.0332 (5)0.0398 (6)0.0580 (7)0.0003 (4)0.0001 (5)0.0006 (5)
C170.0383 (6)0.0358 (5)0.0590 (7)0.0044 (4)0.0030 (5)0.0009 (5)
C70.0539 (7)0.0509 (7)0.0454 (6)0.0012 (6)0.0018 (6)0.0122 (5)
C60.0447 (6)0.0431 (6)0.0502 (6)0.0005 (5)0.0015 (5)0.0055 (5)
C10.0380 (5)0.0459 (6)0.0436 (6)0.0002 (5)0.0013 (5)0.0027 (5)
C20.0542 (8)0.0633 (8)0.0445 (6)0.0007 (7)0.0022 (6)0.0024 (6)
C80.0456 (6)0.0537 (7)0.0401 (5)0.0005 (5)0.0007 (5)0.0024 (5)
C90.0449 (6)0.0455 (6)0.0448 (6)0.0005 (5)0.0007 (5)0.0024 (5)
C50.0677 (9)0.0434 (7)0.0733 (9)0.0018 (7)0.0003 (8)0.0034 (6)
C130.0621 (8)0.0765 (10)0.0430 (6)0.0068 (8)0.0006 (6)0.0021 (6)
C30.0654 (9)0.0726 (10)0.0600 (8)0.0002 (8)0.0016 (7)0.0194 (7)
C40.0734 (11)0.0490 (8)0.0875 (12)0.0013 (8)0.0002 (9)0.0156 (7)
C100.0775 (11)0.0462 (8)0.0634 (9)0.0004 (7)0.0029 (8)0.0020 (6)
C120.0763 (11)0.0866 (12)0.0549 (8)0.0103 (9)0.0064 (8)0.0228 (8)
C110.0876 (13)0.0608 (10)0.0775 (11)0.0054 (9)0.0055 (10)0.0201 (8)
Geometric parameters (Å, º) top
O3—C161.3571 (14)C7—H70.96 (2)
O3—H160.93 (2)C6—C51.424 (2)
O2—C141.2611 (17)C6—C11.4265 (17)
O1—C141.2735 (16)C1—C21.4130 (18)
N2—C181.3679 (17)C2—C31.359 (2)
N2—H2B0.87 (2)C2—H20.939 (19)
N2—H2A0.98 (2)C8—C131.4250 (19)
N1—C11.3532 (17)C8—C91.4258 (17)
N1—C91.3538 (16)C9—C101.412 (2)
N1—H1A1.043 (19)C5—C41.354 (3)
C15—C201.3973 (16)C5—H50.98 (2)
C15—C161.4086 (16)C13—C121.351 (3)
C15—C141.4802 (16)C13—H131.03 (2)
C18—C171.3939 (17)C3—C41.414 (3)
C18—C191.4110 (18)C3—H31.03 (2)
C16—C171.3862 (18)C4—H40.98 (2)
C20—C191.3736 (19)C10—C111.359 (2)
C20—H200.96 (2)C10—H100.98 (2)
C19—H191.004 (17)C12—C111.419 (3)
C17—H170.98 (2)C12—H121.10 (2)
C7—C81.3912 (19)C11—H111.01 (3)
C7—C61.3915 (19)
C16—O3—H16100.5 (14)N1—C1—C2120.26 (11)
C18—N2—H2B118.4 (14)N1—C1—C6119.91 (11)
C18—N2—H2A116.6 (12)C2—C1—C6119.83 (12)
H2B—N2—H2A123.7 (18)C3—C2—C1119.59 (14)
C1—N1—C9122.64 (10)C3—C2—H2123.6 (11)
C1—N1—H1A121.1 (10)C1—C2—H2116.7 (11)
C9—N1—H1A116.2 (10)C7—C8—C13123.20 (13)
C20—C15—C16117.34 (11)C7—C8—C9118.38 (12)
C20—C15—C14121.73 (10)C13—C8—C9118.42 (13)
C16—C15—C14120.90 (11)N1—C9—C10120.29 (13)
O2—C14—O1122.70 (12)N1—C9—C8119.57 (12)
O2—C14—C15119.11 (11)C10—C9—C8120.14 (13)
O1—C14—C15118.19 (11)C4—C5—C6120.37 (15)
N2—C18—C17120.69 (12)C4—C5—H5122.4 (12)
N2—C18—C19120.46 (12)C6—C5—H5117.2 (12)
C17—C18—C19118.84 (12)C12—C13—C8120.24 (15)
O3—C16—C17117.86 (11)C12—C13—H13120.9 (12)
O3—C16—C15121.04 (11)C8—C13—H13118.9 (12)
C17—C16—C15121.07 (11)C2—C3—C4121.15 (14)
C19—C20—C15122.30 (11)C2—C3—H3119.7 (11)
C19—C20—H20120.2 (12)C4—C3—H3119.1 (11)
C15—C20—H20117.5 (12)C5—C4—C3120.65 (15)
C20—C19—C18119.80 (11)C5—C4—H4123.2 (12)
C20—C19—H19121.6 (10)C3—C4—H4116.1 (12)
C18—C19—H19118.5 (9)C11—C10—C9119.25 (16)
C16—C17—C18120.55 (11)C11—C10—H10122.7 (12)
C16—C17—H17117.5 (11)C9—C10—H10118.0 (12)
C18—C17—H17121.8 (11)C13—C12—C11120.67 (15)
C8—C7—C6121.48 (11)C13—C12—H12118.9 (13)
C8—C7—H7119.6 (12)C11—C12—H12120.5 (13)
C6—C7—H7118.9 (12)C10—C11—C12121.28 (17)
C7—C6—C5123.56 (13)C10—C11—H11117.7 (14)
C7—C6—C1118.02 (12)C12—C11—H11120.7 (14)
C5—C6—C1118.41 (13)
C20—C15—C14—O2170.66 (12)C5—C6—C1—C20.07 (19)
C16—C15—C14—O211.57 (17)N1—C1—C2—C3179.29 (14)
C20—C15—C14—O19.93 (17)C6—C1—C2—C30.4 (2)
C16—C15—C14—O1167.84 (12)C6—C7—C8—C13179.61 (14)
C20—C15—C16—O3178.85 (11)C6—C7—C8—C90.1 (2)
C14—C15—C16—O33.29 (18)C1—N1—C9—C10179.98 (14)
C20—C15—C16—C173.07 (17)C1—N1—C9—C80.09 (19)
C14—C15—C16—C17174.79 (11)C7—C8—C9—N10.3 (2)
C16—C15—C20—C191.69 (18)C13—C8—C9—N1179.84 (13)
C14—C15—C20—C19176.15 (12)C7—C8—C9—C10179.79 (15)
C15—C20—C19—C181.4 (2)C13—C8—C9—C100.2 (2)
N2—C18—C19—C20176.39 (13)C7—C6—C5—C4179.90 (17)
C17—C18—C19—C203.10 (19)C1—C6—C5—C40.2 (3)
O3—C16—C17—C18179.53 (12)C7—C8—C13—C12179.78 (17)
C15—C16—C17—C181.39 (19)C9—C8—C13—C120.2 (2)
N2—C18—C17—C16177.76 (13)C1—C2—C3—C40.4 (3)
C19—C18—C17—C161.74 (19)C6—C5—C4—C30.2 (3)
C8—C7—C6—C5179.80 (15)C2—C3—C4—C50.1 (3)
C8—C7—C6—C10.3 (2)N1—C9—C10—C11179.63 (17)
C9—N1—C1—C2179.98 (12)C8—C9—C10—C110.5 (3)
C9—N1—C1—C60.31 (19)C8—C13—C12—C110.5 (3)
C7—C6—C1—N10.51 (19)C9—C10—C11—C120.7 (3)
C5—C6—C1—N1179.60 (14)C13—C12—C11—C100.7 (3)
C7—C6—C1—C2179.82 (13)
Acridin-1-ium 5-chloro-2-hydroxybenzoate (II) top
Crystal data top
C13H10N+·C7H4ClO3F(000) = 728
Mr = 351.77Dx = 1.423 Mg m3
Dm = 0.0 Mg m3
Dm measured by ?
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.4959 (7) ÅCell parameters from 8175 reflections
b = 8.3756 (9) Åθ = 2.7–28.3°
c = 17.4500 (16) ŵ = 0.25 mm1
β = 102.255 (2)°T = 293 K
V = 1641.9 (3) Å3Needle, colourless
Z = 40.59 × 0.18 × 0.14 mm
Data collection top
Bruker D8 QUEST ECO
diffractometer
2710 reflections with I > 2σ(I)
ω and phi scansRint = 0
Absorption correction: multi-scanθmax = 28.0°, θmin = 2.7°
Tmin = 0.867, Tmax = 0.966h = 1515
3797 measured reflectionsk = 1111
3797 independent reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.4066P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
3797 reflectionsΔρmax = 0.30 e Å3
227 parametersΔρmin = 0.35 e Å3
0 restraints
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. Diagrams and publication material were generated using PLATON (Spek, 2020), OLEX2 (Dolomanov et al., 2009) and Mercury software (Macrae et al., 2020).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.02038 (4)0.33762 (8)0.58099 (4)0.0674 (2)
O30.47198 (12)0.37110 (19)0.75929 (9)0.0570 (4)
H150.5115830.4324020.7385170.086*
O10.38228 (12)0.61637 (18)0.55023 (9)0.0585 (4)
O20.51752 (12)0.56169 (19)0.65882 (9)0.0620 (4)
N10.51215 (12)0.78413 (17)0.47126 (8)0.0359 (3)
H1A0.4807570.7205220.4998620.043*
C190.20871 (14)0.4396 (2)0.60411 (10)0.0366 (4)
H190.1849220.4958170.5574410.044*
C10.44264 (14)0.84074 (19)0.40423 (10)0.0350 (4)
C150.36035 (15)0.3636 (2)0.71594 (10)0.0387 (4)
C140.32583 (14)0.44966 (18)0.64566 (10)0.0328 (3)
C130.62853 (14)0.8226 (2)0.49551 (10)0.0357 (4)
C60.49201 (15)0.9474 (2)0.35612 (11)0.0394 (4)
C20.32168 (15)0.7957 (2)0.38217 (12)0.0434 (4)
H20.2887850.7266130.4135340.052*
C200.41509 (15)0.5503 (2)0.61573 (11)0.0408 (4)
C80.68087 (15)0.9315 (2)0.45005 (11)0.0396 (4)
C180.12773 (15)0.3467 (2)0.63185 (11)0.0412 (4)
C120.69649 (16)0.7561 (2)0.56482 (11)0.0460 (4)
H120.6622440.6844500.5942670.055*
C70.61122 (16)0.9911 (2)0.38130 (11)0.0449 (4)
H70.6447611.0621360.3511560.054*
C170.16219 (18)0.2584 (2)0.70030 (12)0.0494 (5)
H170.1074140.1937700.7178410.059*
C30.25381 (17)0.8544 (2)0.31448 (12)0.0504 (5)
H30.1740410.8254280.3002140.060*
C160.27762 (18)0.2671 (2)0.74186 (12)0.0488 (5)
H160.3008640.2082280.7877320.059*
C40.30187 (18)0.9583 (2)0.26544 (13)0.0541 (5)
H40.2539670.9958030.2191660.065*
C50.41750 (18)1.0036 (3)0.28557 (12)0.0513 (5)
H50.4484291.0721220.2529700.062*
C110.81339 (17)0.7983 (3)0.58818 (12)0.0544 (5)
H110.8590430.7534610.6334730.065*
C90.80272 (17)0.9732 (3)0.47799 (13)0.0540 (5)
H90.8388911.0455290.4499710.065*
C100.86605 (17)0.9085 (3)0.54484 (13)0.0585 (6)
H100.9453930.9371050.5624840.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0345 (3)0.0876 (4)0.0776 (4)0.0152 (2)0.0062 (2)0.0076 (3)
O30.0451 (8)0.0682 (10)0.0506 (9)0.0029 (7)0.0062 (6)0.0089 (7)
O10.0437 (7)0.0713 (9)0.0586 (9)0.0188 (7)0.0064 (6)0.0233 (7)
O20.0360 (7)0.0773 (10)0.0673 (10)0.0178 (7)0.0011 (6)0.0098 (8)
N10.0326 (7)0.0365 (7)0.0395 (8)0.0077 (6)0.0099 (6)0.0001 (6)
C190.0367 (8)0.0372 (8)0.0358 (9)0.0023 (7)0.0072 (7)0.0023 (7)
C10.0336 (8)0.0323 (8)0.0398 (9)0.0007 (6)0.0092 (7)0.0031 (7)
C150.0384 (9)0.0390 (9)0.0372 (9)0.0040 (7)0.0046 (7)0.0005 (7)
C140.0335 (8)0.0309 (8)0.0343 (8)0.0011 (6)0.0079 (6)0.0024 (6)
C130.0314 (8)0.0387 (9)0.0380 (9)0.0069 (7)0.0093 (7)0.0087 (7)
C60.0399 (9)0.0378 (9)0.0426 (10)0.0000 (7)0.0133 (7)0.0007 (7)
C20.0340 (9)0.0420 (9)0.0530 (11)0.0059 (7)0.0065 (8)0.0013 (8)
C200.0362 (9)0.0387 (9)0.0472 (11)0.0057 (7)0.0084 (7)0.0012 (8)
C80.0343 (8)0.0417 (9)0.0459 (10)0.0083 (7)0.0158 (7)0.0083 (8)
C180.0340 (8)0.0445 (10)0.0460 (10)0.0053 (7)0.0103 (7)0.0012 (8)
C120.0397 (9)0.0556 (11)0.0424 (10)0.0113 (8)0.0079 (8)0.0032 (9)
C70.0439 (10)0.0441 (10)0.0521 (11)0.0059 (8)0.0222 (9)0.0025 (8)
C170.0520 (11)0.0455 (10)0.0566 (12)0.0045 (9)0.0247 (9)0.0095 (9)
C30.0358 (9)0.0490 (11)0.0620 (13)0.0005 (8)0.0006 (8)0.0003 (9)
C160.0541 (11)0.0503 (11)0.0437 (11)0.0051 (9)0.0141 (9)0.0148 (9)
C40.0522 (12)0.0545 (12)0.0511 (12)0.0084 (9)0.0010 (9)0.0050 (9)
C50.0526 (11)0.0537 (11)0.0491 (11)0.0017 (9)0.0144 (9)0.0113 (9)
C110.0404 (10)0.0710 (13)0.0477 (12)0.0086 (10)0.0002 (8)0.0076 (10)
C90.0399 (10)0.0634 (13)0.0622 (13)0.0170 (9)0.0185 (9)0.0078 (10)
C100.0337 (9)0.0788 (15)0.0616 (14)0.0163 (10)0.0067 (9)0.0143 (11)
Geometric parameters (Å, º) top
Cl—C181.7467 (18)C2—C31.362 (3)
O3—H150.8200C8—C71.386 (3)
O3—C151.346 (2)C8—C91.425 (3)
O1—C201.254 (2)C18—C171.389 (3)
O2—C201.259 (2)C12—H120.9300
N1—H1A0.8600C12—C111.365 (3)
N1—C11.355 (2)C7—H70.9300
N1—C131.354 (2)C17—H170.9300
C19—H190.9300C17—C161.372 (3)
C19—C141.390 (2)C3—H30.9300
C19—C181.378 (2)C3—C41.413 (3)
C1—C61.424 (2)C16—H160.9300
C1—C21.413 (2)C4—H40.9300
C15—C141.405 (2)C4—C51.355 (3)
C15—C161.394 (3)C5—H50.9300
C14—C201.505 (2)C11—H110.9300
C13—C81.424 (2)C11—C101.409 (3)
C13—C121.408 (3)C9—H90.9300
C6—C71.396 (3)C9—C101.350 (3)
C6—C51.423 (3)C10—H100.9300
C2—H20.9300
C15—O3—H15109.5C19—C18—C17120.82 (17)
C1—N1—H1A118.3C17—C18—Cl118.89 (14)
C13—N1—H1A118.3C13—C12—H12120.5
C13—N1—C1123.32 (15)C11—C12—C13119.05 (18)
C14—C19—H19119.9C11—C12—H12120.5
C18—C19—H19119.9C6—C7—H7119.1
C18—C19—C14120.19 (16)C8—C7—C6121.72 (17)
N1—C1—C6119.53 (15)C8—C7—H7119.1
N1—C1—C2120.51 (16)C18—C17—H17120.2
C2—C1—C6119.96 (16)C16—C17—C18119.55 (17)
O3—C15—C14121.72 (16)C16—C17—H17120.2
O3—C15—C16118.65 (16)C2—C3—H3119.3
C16—C15—C14119.64 (16)C2—C3—C4121.48 (18)
C19—C14—C15119.16 (15)C4—C3—H3119.3
C19—C14—C20120.62 (15)C15—C16—H16119.7
C15—C14—C20120.22 (15)C17—C16—C15120.60 (17)
N1—C13—C8119.01 (16)C17—C16—H16119.7
N1—C13—C12120.38 (16)C3—C4—H4119.9
C12—C13—C8120.61 (16)C5—C4—C3120.24 (19)
C7—C6—C1117.82 (17)C5—C4—H4119.9
C7—C6—C5123.77 (17)C6—C5—H5119.7
C5—C6—C1118.42 (16)C4—C5—C6120.60 (18)
C1—C2—H2120.4C4—C5—H5119.7
C3—C2—C1119.29 (18)C12—C11—H11119.4
C3—C2—H2120.4C12—C11—C10121.1 (2)
O1—C20—O2124.98 (17)C10—C11—H11119.4
O1—C20—C14117.93 (15)C8—C9—H9119.7
O2—C20—C14117.09 (16)C10—C9—C8120.50 (19)
C13—C8—C9117.86 (18)C10—C9—H9119.7
C7—C8—C13118.57 (16)C11—C10—H10119.6
C7—C8—C9123.57 (17)C9—C10—C11120.82 (18)
C19—C18—Cl120.29 (14)C9—C10—H10119.6
Cl—C18—C17—C16178.51 (15)C13—N1—C1—C2179.89 (16)
O3—C15—C14—C19178.79 (16)C13—C8—C7—C60.2 (3)
O3—C15—C14—C201.6 (3)C13—C8—C9—C101.1 (3)
O3—C15—C16—C17178.71 (18)C13—C12—C11—C101.0 (3)
N1—C1—C6—C71.0 (2)C6—C1—C2—C30.4 (3)
N1—C1—C6—C5179.27 (16)C2—C1—C6—C7178.60 (16)
N1—C1—C2—C3179.99 (17)C2—C1—C6—C51.2 (3)
N1—C13—C8—C71.7 (2)C2—C3—C4—C50.8 (3)
N1—C13—C8—C9178.38 (16)C8—C13—C12—C110.4 (3)
N1—C13—C12—C11179.40 (17)C8—C9—C10—C110.2 (3)
C19—C14—C20—O14.2 (3)C18—C19—C14—C150.2 (2)
C19—C14—C20—O2175.69 (17)C18—C19—C14—C20179.75 (16)
C19—C18—C17—C161.7 (3)C18—C17—C16—C150.1 (3)
C1—N1—C13—C81.9 (2)C12—C13—C8—C7178.54 (17)
C1—N1—C13—C12178.32 (16)C12—C13—C8—C91.4 (3)
C1—C6—C7—C81.1 (3)C12—C11—C10—C91.3 (3)
C1—C6—C5—C40.9 (3)C7—C6—C5—C4178.82 (19)
C1—C2—C3—C40.6 (3)C7—C8—C9—C10178.8 (2)
C15—C14—C20—O1175.32 (17)C3—C4—C5—C60.0 (3)
C15—C14—C20—O24.8 (2)C16—C15—C14—C191.4 (2)
C14—C19—C18—Cl178.45 (13)C16—C15—C14—C20178.15 (16)
C14—C19—C18—C171.8 (3)C5—C6—C7—C8179.14 (18)
C14—C15—C16—C171.5 (3)C9—C8—C7—C6179.87 (18)
C13—N1—C1—C60.6 (2)
Acridin-1-ium 2-benzamidoacetate monohydrate (III) top
Crystal data top
C13H10N+·C9H8NO3·H2OF(000) = 792
Mr = 376.40Dx = 1.329 Mg m3
Dm = 0.0 Mg m3
Dm measured by ?
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.3436 (13) ÅCell parameters from 20467 reflections
b = 11.0761 (15) Åθ = 2.5–28.3°
c = 23.123 (3) ŵ = 0.09 mm1
β = 90.835 (5)°T = 293 K
V = 1880.6 (5) Å3Block, yellow
Z = 40.32 × 0.25 × 0.13 mm
Data collection top
Bruker D8 QUEST ECO
diffractometer
3285 reflections with I > 2σ(I)
ω and phi scansRint = 0.041
Absorption correction: multi-scanθmax = 28.3°, θmin = 2.6°
Tmin = 0.659, Tmax = 0.746h = 99
20467 measured reflectionsk = 1214
4682 independent reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.055P)2 + 1.0207P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
4682 reflectionsΔρmax = 0.27 e Å3
256 parametersΔρmin = 0.24 e Å3
0 restraints
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. Diagrams and publication material were generated using PLATON (Spek, 2020), OLEX2 (Dolomanov et al., 2009) and Mercury software (Macrae et al., 2020).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2694 (2)0.63814 (15)0.52712 (7)0.0355 (4)
H10.2822360.7088970.5419500.043*
N20.6465 (2)0.94285 (17)0.63485 (8)0.0444 (4)
H2A0.7511200.9393660.6186780.053*
O10.4802 (2)0.89391 (19)0.71219 (8)0.0659 (5)
O40.1047 (3)0.8844 (2)0.54402 (8)0.0670 (5)
H4A0.0011970.9174340.5489520.100*
H4B0.1504980.9198980.5146380.100*
C90.3180 (3)0.54168 (18)0.55938 (8)0.0333 (4)
C190.7671 (3)0.79872 (19)0.70331 (8)0.0385 (5)
C10.2021 (2)0.62926 (18)0.47302 (8)0.0341 (4)
O20.2294 (3)0.9986 (2)0.55713 (11)0.0939 (8)
C80.2979 (3)0.42387 (18)0.53591 (9)0.0361 (4)
C200.6182 (3)0.8822 (2)0.68382 (9)0.0419 (5)
C60.1810 (3)0.51312 (19)0.44740 (8)0.0371 (4)
C70.2296 (3)0.41231 (19)0.47987 (9)0.0397 (5)
H70.2161790.3357960.4637980.048*
C100.3887 (3)0.5582 (2)0.61573 (9)0.0428 (5)
H100.4029010.6353940.6309070.051*
C180.9486 (3)0.8185 (2)0.69102 (10)0.0440 (5)
H180.9816950.8842950.6685210.053*
O30.3874 (3)0.83296 (18)0.57241 (11)0.0996 (9)
C20.1533 (3)0.7344 (2)0.44199 (10)0.0439 (5)
H20.1661440.8101980.4588740.053*
C140.7208 (3)0.6983 (2)0.73600 (9)0.0483 (6)
H140.5993400.6843610.7446550.058*
C50.1114 (3)0.5072 (2)0.38990 (9)0.0481 (6)
H50.0963850.4326330.3720070.058*
C210.5035 (3)1.0138 (2)0.60906 (11)0.0499 (6)
H21A0.5572181.0711590.5826110.060*
H21B0.4445131.0595220.6392640.060*
C130.3496 (3)0.3241 (2)0.57120 (10)0.0487 (6)
H130.3381260.2458970.5569520.058*
C110.4358 (3)0.4597 (2)0.64768 (10)0.0502 (6)
H110.4823600.4700130.6849730.060*
C171.0807 (3)0.7406 (2)0.71208 (11)0.0529 (6)
H171.2028410.7555040.7047760.063*
C150.8516 (4)0.6195 (2)0.75567 (10)0.0568 (6)
H150.8185300.5518400.7768930.068*
C161.0314 (4)0.6408 (2)0.74398 (10)0.0564 (7)
H161.1203470.5877110.7575780.068*
C120.4152 (3)0.3424 (2)0.62519 (11)0.0530 (6)
H120.4474760.2763820.6479790.064*
C220.3606 (3)0.9421 (2)0.57665 (11)0.0533 (6)
C30.0874 (3)0.7232 (3)0.38734 (10)0.0552 (6)
H30.0551750.7922380.3667020.066*
C40.0666 (3)0.6092 (3)0.36098 (10)0.0574 (7)
H40.0215900.6041850.3232540.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0393 (9)0.0300 (8)0.0370 (9)0.0031 (7)0.0013 (7)0.0034 (7)
N20.0354 (9)0.0445 (10)0.0531 (11)0.0002 (8)0.0042 (8)0.0022 (9)
O10.0458 (10)0.0932 (15)0.0587 (11)0.0131 (10)0.0070 (8)0.0052 (10)
O40.0577 (11)0.0835 (14)0.0599 (11)0.0074 (10)0.0028 (9)0.0100 (10)
C90.0297 (9)0.0368 (10)0.0334 (10)0.0000 (8)0.0029 (8)0.0002 (8)
C190.0400 (11)0.0438 (12)0.0315 (10)0.0013 (9)0.0044 (8)0.0110 (9)
C10.0274 (9)0.0400 (11)0.0349 (10)0.0026 (8)0.0021 (8)0.0001 (8)
O20.0671 (13)0.0868 (15)0.126 (2)0.0089 (12)0.0494 (13)0.0332 (14)
C80.0350 (10)0.0347 (10)0.0387 (11)0.0001 (8)0.0060 (8)0.0012 (8)
C200.0380 (11)0.0469 (12)0.0405 (11)0.0013 (10)0.0040 (9)0.0123 (10)
C60.0350 (10)0.0428 (11)0.0337 (10)0.0029 (9)0.0034 (8)0.0050 (9)
C70.0412 (11)0.0356 (11)0.0426 (11)0.0027 (9)0.0059 (9)0.0105 (9)
C100.0439 (12)0.0468 (12)0.0377 (11)0.0008 (10)0.0010 (9)0.0043 (9)
C180.0427 (12)0.0436 (12)0.0456 (12)0.0044 (10)0.0058 (9)0.0071 (10)
O30.126 (2)0.0430 (11)0.128 (2)0.0118 (12)0.0673 (16)0.0174 (12)
C20.0421 (12)0.0415 (12)0.0480 (12)0.0004 (10)0.0000 (10)0.0054 (10)
C140.0501 (13)0.0581 (14)0.0367 (11)0.0053 (11)0.0016 (10)0.0031 (10)
C50.0463 (12)0.0590 (14)0.0389 (11)0.0023 (11)0.0010 (9)0.0113 (11)
C210.0497 (13)0.0311 (11)0.0685 (15)0.0014 (10)0.0104 (11)0.0010 (10)
C130.0541 (14)0.0368 (12)0.0552 (14)0.0058 (10)0.0047 (11)0.0047 (10)
C110.0512 (13)0.0634 (15)0.0358 (11)0.0031 (12)0.0036 (10)0.0052 (11)
C170.0387 (12)0.0608 (15)0.0587 (14)0.0034 (11)0.0070 (10)0.0147 (12)
C150.0702 (17)0.0552 (15)0.0450 (13)0.0034 (13)0.0011 (12)0.0026 (11)
C160.0646 (16)0.0551 (15)0.0492 (14)0.0164 (13)0.0119 (12)0.0082 (12)
C120.0569 (15)0.0516 (14)0.0507 (14)0.0098 (12)0.0034 (11)0.0166 (11)
C220.0585 (15)0.0469 (14)0.0541 (14)0.0105 (11)0.0193 (12)0.0113 (11)
C30.0557 (14)0.0634 (16)0.0463 (13)0.0039 (12)0.0045 (11)0.0161 (12)
C40.0565 (15)0.0812 (19)0.0342 (12)0.0012 (14)0.0078 (10)0.0008 (12)
Geometric parameters (Å, º) top
N1—H10.8600C18—C171.381 (3)
N1—C91.348 (2)O3—C221.229 (3)
N1—C11.342 (2)C2—H20.9300
N2—H2A0.8600C2—C31.352 (3)
N2—C201.336 (3)C14—H140.9300
N2—C211.435 (3)C14—C151.370 (3)
O1—C201.222 (3)C5—H50.9300
O4—H4A0.8501C5—C41.351 (4)
O4—H4B0.8502C21—H21A0.9700
C9—C81.420 (3)C21—H21B0.9700
C9—C101.407 (3)C21—C221.506 (3)
C19—C201.497 (3)C13—H130.9300
C19—C181.384 (3)C13—C121.347 (3)
C19—C141.390 (3)C11—H110.9300
C1—C61.424 (3)C11—C121.407 (4)
C1—C21.412 (3)C17—H170.9300
O2—C221.230 (3)C17—C161.381 (4)
C8—C71.389 (3)C15—H150.9300
C8—C131.422 (3)C15—C161.372 (4)
C6—C71.389 (3)C16—H160.9300
C6—C51.419 (3)C12—H120.9300
C7—H70.9300C3—H30.9300
C10—H100.9300C3—C41.409 (4)
C10—C111.359 (3)C4—H40.9300
C18—H180.9300
C9—N1—H1118.4C15—C14—C19121.0 (2)
C1—N1—H1118.4C15—C14—H14119.5
C1—N1—C9123.27 (17)C6—C5—H5119.8
C20—N2—H2A119.8C4—C5—C6120.5 (2)
C20—N2—C21120.4 (2)C4—C5—H5119.8
C21—N2—H2A119.8N2—C21—H21A108.6
H4A—O4—H4B104.5N2—C21—H21B108.6
N1—C9—C8119.45 (17)N2—C21—C22114.75 (19)
N1—C9—C10120.03 (18)H21A—C21—H21B107.6
C10—C9—C8120.52 (18)C22—C21—H21A108.6
C18—C19—C20122.8 (2)C22—C21—H21B108.6
C18—C19—C14118.8 (2)C8—C13—H13119.9
C14—C19—C20118.4 (2)C12—C13—C8120.2 (2)
N1—C1—C6119.37 (18)C12—C13—H13119.9
N1—C1—C2120.05 (19)C10—C11—H11119.5
C2—C1—C6120.58 (18)C10—C11—C12121.0 (2)
C9—C8—C13117.99 (19)C12—C11—H11119.5
C7—C8—C9118.39 (18)C18—C17—H17120.0
C7—C8—C13123.6 (2)C18—C17—C16120.0 (2)
N2—C20—C19116.35 (19)C16—C17—H17120.0
O1—C20—N2122.9 (2)C14—C15—H15120.1
O1—C20—C19120.8 (2)C14—C15—C16119.8 (2)
C7—C6—C1118.42 (18)C16—C15—H15120.1
C7—C6—C5123.8 (2)C17—C16—H16119.9
C5—C6—C1117.8 (2)C15—C16—C17120.2 (2)
C8—C7—C6121.10 (19)C15—C16—H16119.9
C8—C7—H7119.5C13—C12—C11121.1 (2)
C6—C7—H7119.5C13—C12—H12119.4
C9—C10—H10120.4C11—C12—H12119.4
C11—C10—C9119.1 (2)O2—C22—C21116.8 (2)
C11—C10—H10120.4O3—C22—O2126.7 (2)
C19—C18—H18119.9O3—C22—C21116.5 (2)
C17—C18—C19120.1 (2)C2—C3—H3119.3
C17—C18—H18119.9C2—C3—C4121.4 (2)
C1—C2—H2120.5C4—C3—H3119.3
C3—C2—C1119.0 (2)C5—C4—C3120.7 (2)
C3—C2—H2120.5C5—C4—H4119.6
C19—C14—H14119.5C3—C4—H4119.6
N1—C9—C8—C70.5 (3)C20—C19—C14—C15179.2 (2)
N1—C9—C8—C13179.72 (19)C6—C1—C2—C30.5 (3)
N1—C9—C10—C11179.6 (2)C6—C5—C4—C30.3 (4)
N1—C1—C6—C70.7 (3)C7—C8—C13—C12179.8 (2)
N1—C1—C6—C5179.31 (18)C7—C6—C5—C4179.9 (2)
N1—C1—C2—C3179.3 (2)C10—C9—C8—C7179.22 (19)
N2—C21—C22—O2175.4 (2)C10—C9—C8—C130.5 (3)
N2—C21—C22—O34.7 (4)C10—C11—C12—C130.5 (4)
C9—N1—C1—C60.5 (3)C18—C19—C20—N229.3 (3)
C9—N1—C1—C2179.65 (18)C18—C19—C20—O1149.9 (2)
C9—C8—C7—C60.3 (3)C18—C19—C14—C150.3 (3)
C9—C8—C13—C120.1 (3)C18—C17—C16—C151.1 (4)
C9—C10—C11—C120.1 (3)C2—C1—C6—C7179.46 (19)
C19—C18—C17—C162.0 (3)C2—C1—C6—C50.5 (3)
C19—C14—C15—C161.2 (4)C2—C3—C4—C50.3 (4)
C1—N1—C9—C80.1 (3)C14—C19—C20—N2151.83 (19)
C1—N1—C9—C10179.64 (19)C14—C19—C20—O129.0 (3)
C1—C6—C7—C80.3 (3)C14—C19—C18—C171.3 (3)
C1—C6—C5—C40.1 (3)C14—C15—C16—C170.5 (4)
C1—C2—C3—C40.1 (4)C5—C6—C7—C8179.7 (2)
C8—C9—C10—C110.6 (3)C21—N2—C20—O18.3 (3)
C8—C13—C12—C110.6 (4)C21—N2—C20—C19172.53 (18)
C20—N2—C21—C2277.4 (3)C13—C8—C7—C6179.9 (2)
C20—C19—C18—C17177.5 (2)
Hydrogen-bonding interactions (Å, °) in salts I, II and III top
D—H···AD—HH···AD···AD—H···A
Salt I
N1—H1A···O11.043 (18)1.549 (18)2.5879 (15)173 (2)
N2—H2B···O1i0.99 (2)2.07 (2)3.0059 (19)158.5 (17)
N2—H2B···O2ii0.87 (2)2.11 (2)2.9796 (18)171.4 (17)
O3—H16···O20.93 (2)1.68 (2)2.556 (16)156 (2)
C19—H19···O3iii1.004 (14)2.564 (15)3.3086 (16)130.8 (12)
Salt II
N1—H1A···O10.861.802.641 (2)166
O3—H15···O20.821.782.507 (2)148
C2—H2···O20.932.573.236 (3)129
C11—H11···O3iv0.932.593.280 (3)131
C12—H12···O20.932.433.318 (2)160
Salt III
N1—H1···O30.861.722.545 (3)159
N2—H2A···O4iii0.862.132.878 (3)145
O4—H4A···O20.851.922.773 (3)177
O4—H4B···O2v0.851.972.815 (3)174
C7—H7···O4vi0.932.583.454 (3)157
C10—H10···O30.932.573.204 (3)25
C11—H11···O1vii0.932.533.369 (3)150
C17—H17···O1iii0.932.553.390 (3)150
Symmetry codes: (i) x, y+1/2, -z+1/2; (ii) -x+1, y+1/2, -z+1/2; (iii) x+1, y, z; (iv) -x+3.2, y+1/2, -z+3/2; (v) -x, -y+2, -z+1; (vi) -x, -y+1, -z+1; (vii) -x+1, y-1/2, -z+3/2.
Topological properties of the intermolecular interactions present in salts I, II and III top
D–H···AH···A (Å)ρ(rcp) (e Å-3)\nabla2ρ(rcp) (e Å-5)G(r) (a.u)V(r) (a.u)H(r)E(r) (a.u)De (kJ mol-1)
Salt I
N1—H1A···O11.549 (18)0.4783.3990.148-0.260-0.112-0.130341.47
O3—H16···O22.07 (2)0.3433.7520.097-0.156-0.058-0.078204.48
Salt II
N1—H1A···O11.800.2983.5240.080-0.125-0.044-0.063164.26
O3—H15···O21.780.4843.8660.154-0.267-0.113-0.133350.42
Salt III
N1—H1···O30.860.3834.2820.115-0.186-0.07-0.093244.73
N2—H2A···O40.860.1512.2490.034-0.044-0.01-0.02257.92
Molecular descriptors of salts I, II and III top
Molecular descriptorsSalt ISalt IISalt III
Energy (eV)
Electron affinity A = [-ELUMO]3.5983.9513.630
Ionization potential I = [-EHOMO]4.5974.9944.567
Global hardness ν = (I - A)/20.5000.5220.469
Electrochemical potential µ =-(I + A)/2-4.098-4.473-4.099
Electrophilicity ω = µ2/2ν16.79419.16417.912
Electronegativity χ = (I + A)/24.0984.4734.099
HOMO energy-4.597-4.994-4.567
LUMO energy-3.598-3.951-3.630
Band gap =[ELUMO - EHUMO]0.9991.0430.937
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds