Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621011189/ef3021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011189/ef3021Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011189/ef3021IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011189/ef3021IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011189/ef3021Isup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011189/ef3021IIsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011189/ef3021IIIsup7.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621011189/ef3021sup8.pdf |
CCDC references: 2048258; 2084162; 2084161
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).
C13H10N+·C7H6NO3− | F(000) = 696 |
Mr = 332.35 | Dx = 1.263 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 20496 reflections |
a = 7.1209 (5) Å | θ = 2.6–28.3° |
b = 12.1988 (12) Å | µ = 0.09 mm−1 |
c = 20.1202 (18) Å | T = 293 K |
V = 1747.8 (3) Å3 | Block, brown |
Z = 4 | 0.88 × 0.50 × 0.23 mm |
Bruker D8 QUEST ECO diffractometer | 3934 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and phi scans | θmax = 28.3°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −9→6 |
Tmin = 0.949, Tmax = 0.981 | k = −16→16 |
20496 measured reflections | l = −26→26 |
4274 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H 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 reflections | Δρmax = 0.19 e Å−3 |
290 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
0 constraints | Absolute structure parameter: 0.0 (9) |
Primary atom site location: structure-invariant direct methods |
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). |
x | y | z | Uiso*/Ueq | ||
O3 | 0.62266 (13) | 0.74164 (9) | 0.29886 (6) | 0.0559 (3) | |
O2 | 0.51812 (15) | 0.57511 (9) | 0.36654 (5) | 0.0552 (3) | |
O1 | 0.22130 (16) | 0.51923 (8) | 0.36038 (6) | 0.0590 (3) | |
N2 | 0.1561 (2) | 0.96426 (10) | 0.19765 (8) | 0.0610 (3) | |
N1 | 0.26192 (16) | 0.37488 (9) | 0.45353 (5) | 0.0442 (2) | |
C15 | 0.29836 (16) | 0.69110 (9) | 0.31332 (6) | 0.0367 (2) | |
C14 | 0.34981 (18) | 0.58939 (10) | 0.34906 (6) | 0.0421 (3) | |
C18 | 0.20294 (17) | 0.87705 (9) | 0.23705 (6) | 0.0417 (2) | |
C16 | 0.43767 (16) | 0.76183 (10) | 0.28820 (6) | 0.0395 (3) | |
C20 | 0.11121 (16) | 0.71904 (10) | 0.30111 (6) | 0.0414 (3) | |
C19 | 0.06189 (17) | 0.80983 (11) | 0.26471 (7) | 0.0437 (3) | |
C17 | 0.39049 (17) | 0.85247 (10) | 0.25015 (7) | 0.0443 (3) | |
C7 | 0.2536 (2) | 0.22836 (11) | 0.55772 (6) | 0.0501 (3) | |
C6 | 0.2548 (2) | 0.18865 (10) | 0.49289 (6) | 0.0460 (3) | |
C1 | 0.25990 (17) | 0.26626 (10) | 0.43989 (6) | 0.0425 (3) | |
C2 | 0.2618 (2) | 0.22936 (13) | 0.37333 (7) | 0.0540 (3) | |
C8 | 0.25627 (19) | 0.34026 (11) | 0.57105 (6) | 0.0465 (3) | |
C9 | 0.26015 (19) | 0.41456 (11) | 0.51636 (6) | 0.0451 (3) | |
C5 | 0.2516 (3) | 0.07505 (12) | 0.47674 (9) | 0.0615 (4) | |
C13 | 0.2540 (2) | 0.38421 (15) | 0.63666 (7) | 0.0605 (4) | |
C3 | 0.2577 (3) | 0.12005 (15) | 0.36041 (8) | 0.0660 (4) | |
C4 | 0.2527 (3) | 0.04228 (15) | 0.41247 (10) | 0.0700 (4) | |
C10 | 0.2624 (3) | 0.52876 (13) | 0.52776 (8) | 0.0624 (4) | |
C12 | 0.2562 (3) | 0.49381 (18) | 0.64618 (9) | 0.0726 (5) | |
C11 | 0.2594 (3) | 0.56670 (16) | 0.59123 (10) | 0.0753 (5) | |
H10 | 0.258 (3) | 0.5774 (17) | 0.4891 (10) | 0.075 (6)* | |
H20 | 0.016 (3) | 0.6723 (16) | 0.3195 (9) | 0.065 (5)* | |
H2B | 0.245 (3) | 0.9962 (16) | 0.1749 (9) | 0.063 (5)* | |
H1A | 0.256 (3) | 0.4329 (15) | 0.4155 (9) | 0.065 (5)* | |
H13 | 0.247 (3) | 0.3311 (17) | 0.6764 (11) | 0.075 (6)* | |
H5 | 0.247 (3) | 0.0230 (17) | 0.5138 (9) | 0.074 (6)* | |
H2 | 0.260 (3) | 0.2835 (14) | 0.3402 (9) | 0.058 (5)* | |
H7 | 0.246 (3) | 0.1771 (16) | 0.5939 (10) | 0.067 (5)* | |
H3 | 0.260 (3) | 0.0930 (16) | 0.3120 (10) | 0.071 (6)* | |
H12 | 0.252 (4) | 0.526 (2) | 0.6973 (11) | 0.094 (7)* | |
H2A | 0.021 (3) | 0.9765 (18) | 0.1899 (10) | 0.073 (6)* | |
H19 | −0.073 (2) | 0.8282 (13) | 0.2554 (8) | 0.049 (4)* | |
H17 | 0.493 (3) | 0.8951 (15) | 0.2308 (9) | 0.059 (5)* | |
H16 | 0.615 (3) | 0.685 (2) | 0.3293 (11) | 0.074 (6)* | |
H4 | 0.257 (4) | −0.0347 (19) | 0.3991 (10) | 0.087 (7)* | |
H11 | 0.272 (3) | 0.648 (2) | 0.5982 (12) | 0.096 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0332 (4) | 0.0517 (5) | 0.0828 (7) | −0.0016 (4) | −0.0030 (4) | 0.0075 (5) |
O2 | 0.0490 (5) | 0.0532 (5) | 0.0635 (6) | 0.0071 (4) | −0.0071 (4) | 0.0059 (4) |
O1 | 0.0595 (6) | 0.0517 (5) | 0.0656 (6) | −0.0103 (5) | −0.0126 (5) | 0.0221 (5) |
N2 | 0.0501 (7) | 0.0453 (6) | 0.0874 (9) | 0.0001 (5) | −0.0023 (6) | 0.0227 (6) |
N1 | 0.0458 (5) | 0.0441 (5) | 0.0425 (5) | −0.0008 (4) | −0.0020 (4) | 0.0051 (4) |
C15 | 0.0367 (5) | 0.0345 (5) | 0.0390 (5) | −0.0016 (4) | 0.0014 (4) | −0.0034 (4) |
C14 | 0.0461 (6) | 0.0404 (6) | 0.0397 (5) | 0.0007 (5) | −0.0007 (4) | −0.0004 (4) |
C18 | 0.0424 (6) | 0.0312 (5) | 0.0515 (6) | −0.0005 (4) | −0.0007 (5) | −0.0018 (4) |
C16 | 0.0334 (5) | 0.0369 (5) | 0.0483 (6) | −0.0015 (4) | 0.0000 (4) | −0.0052 (5) |
C20 | 0.0347 (5) | 0.0405 (6) | 0.0489 (6) | −0.0026 (4) | 0.0043 (5) | 0.0008 (5) |
C19 | 0.0332 (5) | 0.0398 (6) | 0.0580 (7) | 0.0003 (4) | −0.0001 (5) | −0.0006 (5) |
C17 | 0.0383 (6) | 0.0358 (5) | 0.0590 (7) | −0.0044 (4) | 0.0030 (5) | 0.0009 (5) |
C7 | 0.0539 (7) | 0.0509 (7) | 0.0454 (6) | 0.0012 (6) | −0.0018 (6) | 0.0122 (5) |
C6 | 0.0447 (6) | 0.0431 (6) | 0.0502 (6) | 0.0005 (5) | −0.0015 (5) | 0.0055 (5) |
C1 | 0.0380 (5) | 0.0459 (6) | 0.0436 (6) | 0.0002 (5) | −0.0013 (5) | 0.0027 (5) |
C2 | 0.0542 (8) | 0.0633 (8) | 0.0445 (6) | −0.0007 (7) | −0.0022 (6) | −0.0024 (6) |
C8 | 0.0456 (6) | 0.0537 (7) | 0.0401 (5) | −0.0005 (5) | −0.0007 (5) | 0.0024 (5) |
C9 | 0.0449 (6) | 0.0455 (6) | 0.0448 (6) | −0.0005 (5) | 0.0007 (5) | 0.0024 (5) |
C5 | 0.0677 (9) | 0.0434 (7) | 0.0733 (9) | 0.0018 (7) | −0.0003 (8) | 0.0034 (6) |
C13 | 0.0621 (8) | 0.0765 (10) | 0.0430 (6) | −0.0068 (8) | 0.0006 (6) | −0.0021 (6) |
C3 | 0.0654 (9) | 0.0726 (10) | 0.0600 (8) | 0.0002 (8) | −0.0016 (7) | −0.0194 (7) |
C4 | 0.0734 (11) | 0.0490 (8) | 0.0875 (12) | 0.0013 (8) | −0.0002 (9) | −0.0156 (7) |
C10 | 0.0775 (11) | 0.0462 (8) | 0.0634 (9) | −0.0004 (7) | 0.0029 (8) | −0.0020 (6) |
C12 | 0.0763 (11) | 0.0866 (12) | 0.0549 (8) | −0.0103 (9) | 0.0064 (8) | −0.0228 (8) |
C11 | 0.0876 (13) | 0.0608 (10) | 0.0775 (11) | −0.0054 (9) | 0.0055 (10) | −0.0201 (8) |
O3—C16 | 1.3571 (14) | C7—H7 | 0.96 (2) |
O3—H16 | 0.93 (2) | C6—C5 | 1.424 (2) |
O2—C14 | 1.2611 (17) | C6—C1 | 1.4265 (17) |
O1—C14 | 1.2735 (16) | C1—C2 | 1.4130 (18) |
N2—C18 | 1.3679 (17) | C2—C3 | 1.359 (2) |
N2—H2B | 0.87 (2) | C2—H2 | 0.939 (19) |
N2—H2A | 0.98 (2) | C8—C13 | 1.4250 (19) |
N1—C1 | 1.3532 (17) | C8—C9 | 1.4258 (17) |
N1—C9 | 1.3538 (16) | C9—C10 | 1.412 (2) |
N1—H1A | 1.043 (19) | C5—C4 | 1.354 (3) |
C15—C20 | 1.3973 (16) | C5—H5 | 0.98 (2) |
C15—C16 | 1.4086 (16) | C13—C12 | 1.351 (3) |
C15—C14 | 1.4802 (16) | C13—H13 | 1.03 (2) |
C18—C17 | 1.3939 (17) | C3—C4 | 1.414 (3) |
C18—C19 | 1.4110 (18) | C3—H3 | 1.03 (2) |
C16—C17 | 1.3862 (18) | C4—H4 | 0.98 (2) |
C20—C19 | 1.3736 (19) | C10—C11 | 1.359 (2) |
C20—H20 | 0.96 (2) | C10—H10 | 0.98 (2) |
C19—H19 | 1.004 (17) | C12—C11 | 1.419 (3) |
C17—H17 | 0.98 (2) | C12—H12 | 1.10 (2) |
C7—C8 | 1.3912 (19) | C11—H11 | 1.01 (3) |
C7—C6 | 1.3915 (19) | ||
C16—O3—H16 | 100.5 (14) | N1—C1—C2 | 120.26 (11) |
C18—N2—H2B | 118.4 (14) | N1—C1—C6 | 119.91 (11) |
C18—N2—H2A | 116.6 (12) | C2—C1—C6 | 119.83 (12) |
H2B—N2—H2A | 123.7 (18) | C3—C2—C1 | 119.59 (14) |
C1—N1—C9 | 122.64 (10) | C3—C2—H2 | 123.6 (11) |
C1—N1—H1A | 121.1 (10) | C1—C2—H2 | 116.7 (11) |
C9—N1—H1A | 116.2 (10) | C7—C8—C13 | 123.20 (13) |
C20—C15—C16 | 117.34 (11) | C7—C8—C9 | 118.38 (12) |
C20—C15—C14 | 121.73 (10) | C13—C8—C9 | 118.42 (13) |
C16—C15—C14 | 120.90 (11) | N1—C9—C10 | 120.29 (13) |
O2—C14—O1 | 122.70 (12) | N1—C9—C8 | 119.57 (12) |
O2—C14—C15 | 119.11 (11) | C10—C9—C8 | 120.14 (13) |
O1—C14—C15 | 118.19 (11) | C4—C5—C6 | 120.37 (15) |
N2—C18—C17 | 120.69 (12) | C4—C5—H5 | 122.4 (12) |
N2—C18—C19 | 120.46 (12) | C6—C5—H5 | 117.2 (12) |
C17—C18—C19 | 118.84 (12) | C12—C13—C8 | 120.24 (15) |
O3—C16—C17 | 117.86 (11) | C12—C13—H13 | 120.9 (12) |
O3—C16—C15 | 121.04 (11) | C8—C13—H13 | 118.9 (12) |
C17—C16—C15 | 121.07 (11) | C2—C3—C4 | 121.15 (14) |
C19—C20—C15 | 122.30 (11) | C2—C3—H3 | 119.7 (11) |
C19—C20—H20 | 120.2 (12) | C4—C3—H3 | 119.1 (11) |
C15—C20—H20 | 117.5 (12) | C5—C4—C3 | 120.65 (15) |
C20—C19—C18 | 119.80 (11) | C5—C4—H4 | 123.2 (12) |
C20—C19—H19 | 121.6 (10) | C3—C4—H4 | 116.1 (12) |
C18—C19—H19 | 118.5 (9) | C11—C10—C9 | 119.25 (16) |
C16—C17—C18 | 120.55 (11) | C11—C10—H10 | 122.7 (12) |
C16—C17—H17 | 117.5 (11) | C9—C10—H10 | 118.0 (12) |
C18—C17—H17 | 121.8 (11) | C13—C12—C11 | 120.67 (15) |
C8—C7—C6 | 121.48 (11) | C13—C12—H12 | 118.9 (13) |
C8—C7—H7 | 119.6 (12) | C11—C12—H12 | 120.5 (13) |
C6—C7—H7 | 118.9 (12) | C10—C11—C12 | 121.28 (17) |
C7—C6—C5 | 123.56 (13) | C10—C11—H11 | 117.7 (14) |
C7—C6—C1 | 118.02 (12) | C12—C11—H11 | 120.7 (14) |
C5—C6—C1 | 118.41 (13) | ||
C20—C15—C14—O2 | −170.66 (12) | C5—C6—C1—C2 | −0.07 (19) |
C16—C15—C14—O2 | 11.57 (17) | N1—C1—C2—C3 | −179.29 (14) |
C20—C15—C14—O1 | 9.93 (17) | C6—C1—C2—C3 | 0.4 (2) |
C16—C15—C14—O1 | −167.84 (12) | C6—C7—C8—C13 | 179.61 (14) |
C20—C15—C16—O3 | 178.85 (11) | C6—C7—C8—C9 | 0.1 (2) |
C14—C15—C16—O3 | −3.29 (18) | C1—N1—C9—C10 | −179.98 (14) |
C20—C15—C16—C17 | −3.07 (17) | C1—N1—C9—C8 | 0.09 (19) |
C14—C15—C16—C17 | 174.79 (11) | C7—C8—C9—N1 | −0.3 (2) |
C16—C15—C20—C19 | 1.69 (18) | C13—C8—C9—N1 | −179.84 (13) |
C14—C15—C20—C19 | −176.15 (12) | C7—C8—C9—C10 | 179.79 (15) |
C15—C20—C19—C18 | 1.4 (2) | C13—C8—C9—C10 | 0.2 (2) |
N2—C18—C19—C20 | 176.39 (13) | C7—C6—C5—C4 | 179.90 (17) |
C17—C18—C19—C20 | −3.10 (19) | C1—C6—C5—C4 | −0.2 (3) |
O3—C16—C17—C18 | 179.53 (12) | C7—C8—C13—C12 | −179.78 (17) |
C15—C16—C17—C18 | 1.39 (19) | C9—C8—C13—C12 | −0.2 (2) |
N2—C18—C17—C16 | −177.76 (13) | C1—C2—C3—C4 | −0.4 (3) |
C19—C18—C17—C16 | 1.74 (19) | C6—C5—C4—C3 | 0.2 (3) |
C8—C7—C6—C5 | −179.80 (15) | C2—C3—C4—C5 | 0.1 (3) |
C8—C7—C6—C1 | 0.3 (2) | N1—C9—C10—C11 | 179.63 (17) |
C9—N1—C1—C2 | 179.98 (12) | C8—C9—C10—C11 | −0.5 (3) |
C9—N1—C1—C6 | 0.31 (19) | C8—C13—C12—C11 | 0.5 (3) |
C7—C6—C1—N1 | −0.51 (19) | C9—C10—C11—C12 | 0.7 (3) |
C5—C6—C1—N1 | 179.60 (14) | C13—C12—C11—C10 | −0.7 (3) |
C7—C6—C1—C2 | 179.82 (13) |
C13H10N+·C7H4ClO3− | F(000) = 728 |
Mr = 351.77 | Dx = 1.423 Mg m−3 Dm = 0.0 Mg m−3 Dm measured by ? |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4959 (7) Å | Cell parameters from 8175 reflections |
b = 8.3756 (9) Å | θ = 2.7–28.3° |
c = 17.4500 (16) Å | µ = 0.25 mm−1 |
β = 102.255 (2)° | T = 293 K |
V = 1641.9 (3) Å3 | Needle, colourless |
Z = 4 | 0.59 × 0.18 × 0.14 mm |
Bruker D8 QUEST ECO diffractometer | 2710 reflections with I > 2σ(I) |
ω and phi scans | Rint = 0 |
Absorption correction: multi-scan | θmax = 28.0°, θmin = 2.7° |
Tmin = 0.867, Tmax = 0.966 | h = −15→15 |
3797 measured reflections | k = −11→11 |
3797 independent reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-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 reflections | Δρmax = 0.30 e Å−3 |
227 parameters | Δρmin = −0.35 e Å−3 |
0 restraints |
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). |
x | y | z | Uiso*/Ueq | ||
Cl | −0.02038 (4) | 0.33762 (8) | 0.58099 (4) | 0.0674 (2) | |
O3 | 0.47198 (12) | 0.37110 (19) | 0.75929 (9) | 0.0570 (4) | |
H15 | 0.511583 | 0.432402 | 0.738517 | 0.086* | |
O1 | 0.38228 (12) | 0.61637 (18) | 0.55023 (9) | 0.0585 (4) | |
O2 | 0.51752 (12) | 0.56169 (19) | 0.65882 (9) | 0.0620 (4) | |
N1 | 0.51215 (12) | 0.78413 (17) | 0.47126 (8) | 0.0359 (3) | |
H1A | 0.480757 | 0.720522 | 0.499862 | 0.043* | |
C19 | 0.20871 (14) | 0.4396 (2) | 0.60411 (10) | 0.0366 (4) | |
H19 | 0.184922 | 0.495817 | 0.557441 | 0.044* | |
C1 | 0.44264 (14) | 0.84074 (19) | 0.40423 (10) | 0.0350 (4) | |
C15 | 0.36035 (15) | 0.3636 (2) | 0.71594 (10) | 0.0387 (4) | |
C14 | 0.32583 (14) | 0.44966 (18) | 0.64566 (10) | 0.0328 (3) | |
C13 | 0.62853 (14) | 0.8226 (2) | 0.49551 (10) | 0.0357 (4) | |
C6 | 0.49201 (15) | 0.9474 (2) | 0.35612 (11) | 0.0394 (4) | |
C2 | 0.32168 (15) | 0.7957 (2) | 0.38217 (12) | 0.0434 (4) | |
H2 | 0.288785 | 0.726613 | 0.413534 | 0.052* | |
C20 | 0.41509 (15) | 0.5503 (2) | 0.61573 (11) | 0.0408 (4) | |
C8 | 0.68087 (15) | 0.9315 (2) | 0.45005 (11) | 0.0396 (4) | |
C18 | 0.12773 (15) | 0.3467 (2) | 0.63185 (11) | 0.0412 (4) | |
C12 | 0.69649 (16) | 0.7561 (2) | 0.56482 (11) | 0.0460 (4) | |
H12 | 0.662244 | 0.684450 | 0.594267 | 0.055* | |
C7 | 0.61122 (16) | 0.9911 (2) | 0.38130 (11) | 0.0449 (4) | |
H7 | 0.644761 | 1.062136 | 0.351156 | 0.054* | |
C17 | 0.16219 (18) | 0.2584 (2) | 0.70030 (12) | 0.0494 (5) | |
H17 | 0.107414 | 0.193770 | 0.717841 | 0.059* | |
C3 | 0.25381 (17) | 0.8544 (2) | 0.31448 (12) | 0.0504 (5) | |
H3 | 0.174041 | 0.825428 | 0.300214 | 0.060* | |
C16 | 0.27762 (18) | 0.2671 (2) | 0.74186 (12) | 0.0488 (5) | |
H16 | 0.300864 | 0.208228 | 0.787732 | 0.059* | |
C4 | 0.30187 (18) | 0.9583 (2) | 0.26544 (13) | 0.0541 (5) | |
H4 | 0.253967 | 0.995803 | 0.219166 | 0.065* | |
C5 | 0.41750 (18) | 1.0036 (3) | 0.28557 (12) | 0.0513 (5) | |
H5 | 0.448429 | 1.072122 | 0.252970 | 0.062* | |
C11 | 0.81339 (17) | 0.7983 (3) | 0.58818 (12) | 0.0544 (5) | |
H11 | 0.859043 | 0.753461 | 0.633473 | 0.065* | |
C9 | 0.80272 (17) | 0.9732 (3) | 0.47799 (13) | 0.0540 (5) | |
H9 | 0.838891 | 1.045529 | 0.449971 | 0.065* | |
C10 | 0.86605 (17) | 0.9085 (3) | 0.54484 (13) | 0.0585 (6) | |
H10 | 0.945393 | 0.937105 | 0.562484 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0345 (3) | 0.0876 (4) | 0.0776 (4) | −0.0152 (2) | 0.0062 (2) | 0.0076 (3) |
O3 | 0.0451 (8) | 0.0682 (10) | 0.0506 (9) | 0.0029 (7) | −0.0062 (6) | 0.0089 (7) |
O1 | 0.0437 (7) | 0.0713 (9) | 0.0586 (9) | −0.0188 (7) | 0.0064 (6) | 0.0233 (7) |
O2 | 0.0360 (7) | 0.0773 (10) | 0.0673 (10) | −0.0178 (7) | −0.0011 (6) | 0.0098 (8) |
N1 | 0.0326 (7) | 0.0365 (7) | 0.0395 (8) | −0.0077 (6) | 0.0099 (6) | −0.0001 (6) |
C19 | 0.0367 (8) | 0.0372 (8) | 0.0358 (9) | −0.0023 (7) | 0.0072 (7) | 0.0023 (7) |
C1 | 0.0336 (8) | 0.0323 (8) | 0.0398 (9) | −0.0007 (6) | 0.0092 (7) | −0.0031 (7) |
C15 | 0.0384 (9) | 0.0390 (9) | 0.0372 (9) | 0.0040 (7) | 0.0046 (7) | −0.0005 (7) |
C14 | 0.0335 (8) | 0.0309 (8) | 0.0343 (8) | −0.0011 (6) | 0.0079 (6) | −0.0024 (6) |
C13 | 0.0314 (8) | 0.0387 (9) | 0.0380 (9) | −0.0069 (7) | 0.0093 (7) | −0.0087 (7) |
C6 | 0.0399 (9) | 0.0378 (9) | 0.0426 (10) | 0.0000 (7) | 0.0133 (7) | −0.0007 (7) |
C2 | 0.0340 (9) | 0.0420 (9) | 0.0530 (11) | −0.0059 (7) | 0.0065 (8) | 0.0013 (8) |
C20 | 0.0362 (9) | 0.0387 (9) | 0.0472 (11) | −0.0057 (7) | 0.0084 (7) | −0.0012 (8) |
C8 | 0.0343 (8) | 0.0417 (9) | 0.0459 (10) | −0.0083 (7) | 0.0158 (7) | −0.0083 (8) |
C18 | 0.0340 (8) | 0.0445 (10) | 0.0460 (10) | −0.0053 (7) | 0.0103 (7) | −0.0012 (8) |
C12 | 0.0397 (9) | 0.0556 (11) | 0.0424 (10) | −0.0113 (8) | 0.0079 (8) | −0.0032 (9) |
C7 | 0.0439 (10) | 0.0441 (10) | 0.0521 (11) | −0.0059 (8) | 0.0222 (9) | 0.0025 (8) |
C17 | 0.0520 (11) | 0.0455 (10) | 0.0566 (12) | −0.0045 (9) | 0.0247 (9) | 0.0095 (9) |
C3 | 0.0358 (9) | 0.0490 (11) | 0.0620 (13) | −0.0005 (8) | 0.0006 (8) | 0.0003 (9) |
C16 | 0.0541 (11) | 0.0503 (11) | 0.0437 (11) | 0.0051 (9) | 0.0141 (9) | 0.0148 (9) |
C4 | 0.0522 (12) | 0.0545 (12) | 0.0511 (12) | 0.0084 (9) | 0.0010 (9) | 0.0050 (9) |
C5 | 0.0526 (11) | 0.0537 (11) | 0.0491 (11) | 0.0017 (9) | 0.0144 (9) | 0.0113 (9) |
C11 | 0.0404 (10) | 0.0710 (13) | 0.0477 (12) | −0.0086 (10) | 0.0002 (8) | −0.0076 (10) |
C9 | 0.0399 (10) | 0.0634 (13) | 0.0622 (13) | −0.0170 (9) | 0.0185 (9) | −0.0078 (10) |
C10 | 0.0337 (9) | 0.0788 (15) | 0.0616 (14) | −0.0163 (10) | 0.0067 (9) | −0.0143 (11) |
Cl—C18 | 1.7467 (18) | C2—C3 | 1.362 (3) |
O3—H15 | 0.8200 | C8—C7 | 1.386 (3) |
O3—C15 | 1.346 (2) | C8—C9 | 1.425 (3) |
O1—C20 | 1.254 (2) | C18—C17 | 1.389 (3) |
O2—C20 | 1.259 (2) | C12—H12 | 0.9300 |
N1—H1A | 0.8600 | C12—C11 | 1.365 (3) |
N1—C1 | 1.355 (2) | C7—H7 | 0.9300 |
N1—C13 | 1.354 (2) | C17—H17 | 0.9300 |
C19—H19 | 0.9300 | C17—C16 | 1.372 (3) |
C19—C14 | 1.390 (2) | C3—H3 | 0.9300 |
C19—C18 | 1.378 (2) | C3—C4 | 1.413 (3) |
C1—C6 | 1.424 (2) | C16—H16 | 0.9300 |
C1—C2 | 1.413 (2) | C4—H4 | 0.9300 |
C15—C14 | 1.405 (2) | C4—C5 | 1.355 (3) |
C15—C16 | 1.394 (3) | C5—H5 | 0.9300 |
C14—C20 | 1.505 (2) | C11—H11 | 0.9300 |
C13—C8 | 1.424 (2) | C11—C10 | 1.409 (3) |
C13—C12 | 1.408 (3) | C9—H9 | 0.9300 |
C6—C7 | 1.396 (3) | C9—C10 | 1.350 (3) |
C6—C5 | 1.423 (3) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | ||
C15—O3—H15 | 109.5 | C19—C18—C17 | 120.82 (17) |
C1—N1—H1A | 118.3 | C17—C18—Cl | 118.89 (14) |
C13—N1—H1A | 118.3 | C13—C12—H12 | 120.5 |
C13—N1—C1 | 123.32 (15) | C11—C12—C13 | 119.05 (18) |
C14—C19—H19 | 119.9 | C11—C12—H12 | 120.5 |
C18—C19—H19 | 119.9 | C6—C7—H7 | 119.1 |
C18—C19—C14 | 120.19 (16) | C8—C7—C6 | 121.72 (17) |
N1—C1—C6 | 119.53 (15) | C8—C7—H7 | 119.1 |
N1—C1—C2 | 120.51 (16) | C18—C17—H17 | 120.2 |
C2—C1—C6 | 119.96 (16) | C16—C17—C18 | 119.55 (17) |
O3—C15—C14 | 121.72 (16) | C16—C17—H17 | 120.2 |
O3—C15—C16 | 118.65 (16) | C2—C3—H3 | 119.3 |
C16—C15—C14 | 119.64 (16) | C2—C3—C4 | 121.48 (18) |
C19—C14—C15 | 119.16 (15) | C4—C3—H3 | 119.3 |
C19—C14—C20 | 120.62 (15) | C15—C16—H16 | 119.7 |
C15—C14—C20 | 120.22 (15) | C17—C16—C15 | 120.60 (17) |
N1—C13—C8 | 119.01 (16) | C17—C16—H16 | 119.7 |
N1—C13—C12 | 120.38 (16) | C3—C4—H4 | 119.9 |
C12—C13—C8 | 120.61 (16) | C5—C4—C3 | 120.24 (19) |
C7—C6—C1 | 117.82 (17) | C5—C4—H4 | 119.9 |
C7—C6—C5 | 123.77 (17) | C6—C5—H5 | 119.7 |
C5—C6—C1 | 118.42 (16) | C4—C5—C6 | 120.60 (18) |
C1—C2—H2 | 120.4 | C4—C5—H5 | 119.7 |
C3—C2—C1 | 119.29 (18) | C12—C11—H11 | 119.4 |
C3—C2—H2 | 120.4 | C12—C11—C10 | 121.1 (2) |
O1—C20—O2 | 124.98 (17) | C10—C11—H11 | 119.4 |
O1—C20—C14 | 117.93 (15) | C8—C9—H9 | 119.7 |
O2—C20—C14 | 117.09 (16) | C10—C9—C8 | 120.50 (19) |
C13—C8—C9 | 117.86 (18) | C10—C9—H9 | 119.7 |
C7—C8—C13 | 118.57 (16) | C11—C10—H10 | 119.6 |
C7—C8—C9 | 123.57 (17) | C9—C10—C11 | 120.82 (18) |
C19—C18—Cl | 120.29 (14) | C9—C10—H10 | 119.6 |
Cl—C18—C17—C16 | −178.51 (15) | C13—N1—C1—C2 | 179.89 (16) |
O3—C15—C14—C19 | −178.79 (16) | C13—C8—C7—C6 | 0.2 (3) |
O3—C15—C14—C20 | 1.6 (3) | C13—C8—C9—C10 | 1.1 (3) |
O3—C15—C16—C17 | 178.71 (18) | C13—C12—C11—C10 | 1.0 (3) |
N1—C1—C6—C7 | −1.0 (2) | C6—C1—C2—C3 | 0.4 (3) |
N1—C1—C6—C5 | 179.27 (16) | C2—C1—C6—C7 | 178.60 (16) |
N1—C1—C2—C3 | 179.99 (17) | C2—C1—C6—C5 | −1.2 (3) |
N1—C13—C8—C7 | −1.7 (2) | C2—C3—C4—C5 | −0.8 (3) |
N1—C13—C8—C9 | 178.38 (16) | C8—C13—C12—C11 | 0.4 (3) |
N1—C13—C12—C11 | −179.40 (17) | C8—C9—C10—C11 | 0.2 (3) |
C19—C14—C20—O1 | −4.2 (3) | C18—C19—C14—C15 | 0.2 (2) |
C19—C14—C20—O2 | 175.69 (17) | C18—C19—C14—C20 | 179.75 (16) |
C19—C18—C17—C16 | 1.7 (3) | C18—C17—C16—C15 | −0.1 (3) |
C1—N1—C13—C8 | 1.9 (2) | C12—C13—C8—C7 | 178.54 (17) |
C1—N1—C13—C12 | −178.32 (16) | C12—C13—C8—C9 | −1.4 (3) |
C1—C6—C7—C8 | 1.1 (3) | C12—C11—C10—C9 | −1.3 (3) |
C1—C6—C5—C4 | 0.9 (3) | C7—C6—C5—C4 | −178.82 (19) |
C1—C2—C3—C4 | 0.6 (3) | C7—C8—C9—C10 | −178.8 (2) |
C15—C14—C20—O1 | 175.32 (17) | C3—C4—C5—C6 | 0.0 (3) |
C15—C14—C20—O2 | −4.8 (2) | C16—C15—C14—C19 | 1.4 (2) |
C14—C19—C18—Cl | 178.45 (13) | C16—C15—C14—C20 | −178.15 (16) |
C14—C19—C18—C17 | −1.8 (3) | C5—C6—C7—C8 | −179.14 (18) |
C14—C15—C16—C17 | −1.5 (3) | C9—C8—C7—C6 | −179.87 (18) |
C13—N1—C1—C6 | −0.6 (2) |
C13H10N+·C9H8NO3−·H2O | F(000) = 792 |
Mr = 376.40 | Dx = 1.329 Mg m−3 Dm = 0.0 Mg m−3 Dm measured by ? |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3436 (13) Å | Cell parameters from 20467 reflections |
b = 11.0761 (15) Å | θ = 2.5–28.3° |
c = 23.123 (3) Å | µ = 0.09 mm−1 |
β = 90.835 (5)° | T = 293 K |
V = 1880.6 (5) Å3 | Block, yellow |
Z = 4 | 0.32 × 0.25 × 0.13 mm |
Bruker D8 QUEST ECO diffractometer | 3285 reflections with I > 2σ(I) |
ω and phi scans | Rint = 0.041 |
Absorption correction: multi-scan | θmax = 28.3°, θmin = 2.6° |
Tmin = 0.659, Tmax = 0.746 | h = −9→9 |
20467 measured reflections | k = −12→14 |
4682 independent reflections | l = −30→30 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.071 | H-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 reflections | Δρmax = 0.27 e Å−3 |
256 parameters | Δρmin = −0.24 e Å−3 |
0 restraints |
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). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2694 (2) | 0.63814 (15) | 0.52712 (7) | 0.0355 (4) | |
H1 | 0.282236 | 0.708897 | 0.541950 | 0.043* | |
N2 | 0.6465 (2) | 0.94285 (17) | 0.63485 (8) | 0.0444 (4) | |
H2A | 0.751120 | 0.939366 | 0.618678 | 0.053* | |
O1 | 0.4802 (2) | 0.89391 (19) | 0.71219 (8) | 0.0659 (5) | |
O4 | −0.1047 (3) | 0.8844 (2) | 0.54402 (8) | 0.0670 (5) | |
H4A | −0.001197 | 0.917434 | 0.548952 | 0.100* | |
H4B | −0.150498 | 0.919898 | 0.514638 | 0.100* | |
C9 | 0.3180 (3) | 0.54168 (18) | 0.55938 (8) | 0.0333 (4) | |
C19 | 0.7671 (3) | 0.79872 (19) | 0.70331 (8) | 0.0385 (5) | |
C1 | 0.2021 (2) | 0.62926 (18) | 0.47302 (8) | 0.0341 (4) | |
O2 | 0.2294 (3) | 0.9986 (2) | 0.55713 (11) | 0.0939 (8) | |
C8 | 0.2979 (3) | 0.42387 (18) | 0.53591 (9) | 0.0361 (4) | |
C20 | 0.6182 (3) | 0.8822 (2) | 0.68382 (9) | 0.0419 (5) | |
C6 | 0.1810 (3) | 0.51312 (19) | 0.44740 (8) | 0.0371 (4) | |
C7 | 0.2296 (3) | 0.41231 (19) | 0.47987 (9) | 0.0397 (5) | |
H7 | 0.216179 | 0.335796 | 0.463798 | 0.048* | |
C10 | 0.3887 (3) | 0.5582 (2) | 0.61573 (9) | 0.0428 (5) | |
H10 | 0.402901 | 0.635394 | 0.630907 | 0.051* | |
C18 | 0.9486 (3) | 0.8185 (2) | 0.69102 (10) | 0.0440 (5) | |
H18 | 0.981695 | 0.884295 | 0.668521 | 0.053* | |
O3 | 0.3874 (3) | 0.83296 (18) | 0.57241 (11) | 0.0996 (9) | |
C2 | 0.1533 (3) | 0.7344 (2) | 0.44199 (10) | 0.0439 (5) | |
H2 | 0.166144 | 0.810198 | 0.458874 | 0.053* | |
C14 | 0.7208 (3) | 0.6983 (2) | 0.73600 (9) | 0.0483 (6) | |
H14 | 0.599340 | 0.684361 | 0.744655 | 0.058* | |
C5 | 0.1114 (3) | 0.5072 (2) | 0.38990 (9) | 0.0481 (6) | |
H5 | 0.096385 | 0.432633 | 0.372007 | 0.058* | |
C21 | 0.5035 (3) | 1.0138 (2) | 0.60906 (11) | 0.0499 (6) | |
H21A | 0.557218 | 1.071159 | 0.582611 | 0.060* | |
H21B | 0.444513 | 1.059522 | 0.639264 | 0.060* | |
C13 | 0.3496 (3) | 0.3241 (2) | 0.57120 (10) | 0.0487 (6) | |
H13 | 0.338126 | 0.245897 | 0.556952 | 0.058* | |
C11 | 0.4358 (3) | 0.4597 (2) | 0.64768 (10) | 0.0502 (6) | |
H11 | 0.482360 | 0.470013 | 0.684973 | 0.060* | |
C17 | 1.0807 (3) | 0.7406 (2) | 0.71208 (11) | 0.0529 (6) | |
H17 | 1.202841 | 0.755504 | 0.704776 | 0.063* | |
C15 | 0.8516 (4) | 0.6195 (2) | 0.75567 (10) | 0.0568 (6) | |
H15 | 0.818530 | 0.551840 | 0.776893 | 0.068* | |
C16 | 1.0314 (4) | 0.6408 (2) | 0.74398 (10) | 0.0564 (7) | |
H16 | 1.120347 | 0.587711 | 0.757578 | 0.068* | |
C12 | 0.4152 (3) | 0.3424 (2) | 0.62519 (11) | 0.0530 (6) | |
H12 | 0.447476 | 0.276382 | 0.647979 | 0.064* | |
C22 | 0.3606 (3) | 0.9421 (2) | 0.57665 (11) | 0.0533 (6) | |
C3 | 0.0874 (3) | 0.7232 (3) | 0.38734 (10) | 0.0552 (6) | |
H3 | 0.055175 | 0.792238 | 0.366702 | 0.066* | |
C4 | 0.0666 (3) | 0.6092 (3) | 0.36098 (10) | 0.0574 (7) | |
H4 | 0.021590 | 0.604185 | 0.323254 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0393 (9) | 0.0300 (8) | 0.0370 (9) | −0.0031 (7) | −0.0013 (7) | −0.0034 (7) |
N2 | 0.0354 (9) | 0.0445 (10) | 0.0531 (11) | 0.0002 (8) | −0.0042 (8) | −0.0022 (9) |
O1 | 0.0458 (10) | 0.0932 (15) | 0.0587 (11) | 0.0131 (10) | 0.0070 (8) | −0.0052 (10) |
O4 | 0.0577 (11) | 0.0835 (14) | 0.0599 (11) | −0.0074 (10) | 0.0028 (9) | 0.0100 (10) |
C9 | 0.0297 (9) | 0.0368 (10) | 0.0334 (10) | 0.0000 (8) | 0.0029 (8) | 0.0002 (8) |
C19 | 0.0400 (11) | 0.0438 (12) | 0.0315 (10) | −0.0013 (9) | −0.0044 (8) | −0.0110 (9) |
C1 | 0.0274 (9) | 0.0400 (11) | 0.0349 (10) | −0.0026 (8) | 0.0021 (8) | −0.0001 (8) |
O2 | 0.0671 (13) | 0.0868 (15) | 0.126 (2) | −0.0089 (12) | −0.0494 (13) | 0.0332 (14) |
C8 | 0.0350 (10) | 0.0347 (10) | 0.0387 (11) | 0.0001 (8) | 0.0060 (8) | −0.0012 (8) |
C20 | 0.0380 (11) | 0.0469 (12) | 0.0405 (11) | −0.0013 (10) | −0.0040 (9) | −0.0123 (10) |
C6 | 0.0350 (10) | 0.0428 (11) | 0.0337 (10) | −0.0029 (9) | 0.0034 (8) | −0.0050 (9) |
C7 | 0.0412 (11) | 0.0356 (11) | 0.0426 (11) | −0.0027 (9) | 0.0059 (9) | −0.0105 (9) |
C10 | 0.0439 (12) | 0.0468 (12) | 0.0377 (11) | −0.0008 (10) | −0.0010 (9) | −0.0043 (9) |
C18 | 0.0427 (12) | 0.0436 (12) | 0.0456 (12) | −0.0044 (10) | −0.0058 (9) | −0.0071 (10) |
O3 | 0.126 (2) | 0.0430 (11) | 0.128 (2) | −0.0118 (12) | −0.0673 (16) | −0.0174 (12) |
C2 | 0.0421 (12) | 0.0415 (12) | 0.0480 (12) | −0.0004 (10) | 0.0000 (10) | 0.0054 (10) |
C14 | 0.0501 (13) | 0.0581 (14) | 0.0367 (11) | −0.0053 (11) | 0.0016 (10) | −0.0031 (10) |
C5 | 0.0463 (12) | 0.0590 (14) | 0.0389 (11) | −0.0023 (11) | −0.0010 (9) | −0.0113 (11) |
C21 | 0.0497 (13) | 0.0311 (11) | 0.0685 (15) | −0.0014 (10) | −0.0104 (11) | 0.0010 (10) |
C13 | 0.0541 (14) | 0.0368 (12) | 0.0552 (14) | 0.0058 (10) | 0.0047 (11) | 0.0047 (10) |
C11 | 0.0512 (13) | 0.0634 (15) | 0.0358 (11) | 0.0031 (12) | −0.0036 (10) | 0.0052 (11) |
C17 | 0.0387 (12) | 0.0608 (15) | 0.0587 (14) | 0.0034 (11) | −0.0070 (10) | −0.0147 (12) |
C15 | 0.0702 (17) | 0.0552 (15) | 0.0450 (13) | 0.0034 (13) | −0.0011 (12) | 0.0026 (11) |
C16 | 0.0646 (16) | 0.0551 (15) | 0.0492 (14) | 0.0164 (13) | −0.0119 (12) | −0.0082 (12) |
C12 | 0.0569 (15) | 0.0516 (14) | 0.0507 (14) | 0.0098 (12) | 0.0034 (11) | 0.0166 (11) |
C22 | 0.0585 (15) | 0.0469 (14) | 0.0541 (14) | −0.0105 (11) | −0.0193 (12) | 0.0113 (11) |
C3 | 0.0557 (14) | 0.0634 (16) | 0.0463 (13) | 0.0039 (12) | −0.0045 (11) | 0.0161 (12) |
C4 | 0.0565 (15) | 0.0812 (19) | 0.0342 (12) | 0.0012 (14) | −0.0078 (10) | 0.0008 (12) |
N1—H1 | 0.8600 | C18—C17 | 1.381 (3) |
N1—C9 | 1.348 (2) | O3—C22 | 1.229 (3) |
N1—C1 | 1.342 (2) | C2—H2 | 0.9300 |
N2—H2A | 0.8600 | C2—C3 | 1.352 (3) |
N2—C20 | 1.336 (3) | C14—H14 | 0.9300 |
N2—C21 | 1.435 (3) | C14—C15 | 1.370 (3) |
O1—C20 | 1.222 (3) | C5—H5 | 0.9300 |
O4—H4A | 0.8501 | C5—C4 | 1.351 (4) |
O4—H4B | 0.8502 | C21—H21A | 0.9700 |
C9—C8 | 1.420 (3) | C21—H21B | 0.9700 |
C9—C10 | 1.407 (3) | C21—C22 | 1.506 (3) |
C19—C20 | 1.497 (3) | C13—H13 | 0.9300 |
C19—C18 | 1.384 (3) | C13—C12 | 1.347 (3) |
C19—C14 | 1.390 (3) | C11—H11 | 0.9300 |
C1—C6 | 1.424 (3) | C11—C12 | 1.407 (4) |
C1—C2 | 1.412 (3) | C17—H17 | 0.9300 |
O2—C22 | 1.230 (3) | C17—C16 | 1.381 (4) |
C8—C7 | 1.389 (3) | C15—H15 | 0.9300 |
C8—C13 | 1.422 (3) | C15—C16 | 1.372 (4) |
C6—C7 | 1.389 (3) | C16—H16 | 0.9300 |
C6—C5 | 1.419 (3) | C12—H12 | 0.9300 |
C7—H7 | 0.9300 | C3—H3 | 0.9300 |
C10—H10 | 0.9300 | C3—C4 | 1.409 (4) |
C10—C11 | 1.359 (3) | C4—H4 | 0.9300 |
C18—H18 | 0.9300 | ||
C9—N1—H1 | 118.4 | C15—C14—C19 | 121.0 (2) |
C1—N1—H1 | 118.4 | C15—C14—H14 | 119.5 |
C1—N1—C9 | 123.27 (17) | C6—C5—H5 | 119.8 |
C20—N2—H2A | 119.8 | C4—C5—C6 | 120.5 (2) |
C20—N2—C21 | 120.4 (2) | C4—C5—H5 | 119.8 |
C21—N2—H2A | 119.8 | N2—C21—H21A | 108.6 |
H4A—O4—H4B | 104.5 | N2—C21—H21B | 108.6 |
N1—C9—C8 | 119.45 (17) | N2—C21—C22 | 114.75 (19) |
N1—C9—C10 | 120.03 (18) | H21A—C21—H21B | 107.6 |
C10—C9—C8 | 120.52 (18) | C22—C21—H21A | 108.6 |
C18—C19—C20 | 122.8 (2) | C22—C21—H21B | 108.6 |
C18—C19—C14 | 118.8 (2) | C8—C13—H13 | 119.9 |
C14—C19—C20 | 118.4 (2) | C12—C13—C8 | 120.2 (2) |
N1—C1—C6 | 119.37 (18) | C12—C13—H13 | 119.9 |
N1—C1—C2 | 120.05 (19) | C10—C11—H11 | 119.5 |
C2—C1—C6 | 120.58 (18) | C10—C11—C12 | 121.0 (2) |
C9—C8—C13 | 117.99 (19) | C12—C11—H11 | 119.5 |
C7—C8—C9 | 118.39 (18) | C18—C17—H17 | 120.0 |
C7—C8—C13 | 123.6 (2) | C18—C17—C16 | 120.0 (2) |
N2—C20—C19 | 116.35 (19) | C16—C17—H17 | 120.0 |
O1—C20—N2 | 122.9 (2) | C14—C15—H15 | 120.1 |
O1—C20—C19 | 120.8 (2) | C14—C15—C16 | 119.8 (2) |
C7—C6—C1 | 118.42 (18) | C16—C15—H15 | 120.1 |
C7—C6—C5 | 123.8 (2) | C17—C16—H16 | 119.9 |
C5—C6—C1 | 117.8 (2) | C15—C16—C17 | 120.2 (2) |
C8—C7—C6 | 121.10 (19) | C15—C16—H16 | 119.9 |
C8—C7—H7 | 119.5 | C13—C12—C11 | 121.1 (2) |
C6—C7—H7 | 119.5 | C13—C12—H12 | 119.4 |
C9—C10—H10 | 120.4 | C11—C12—H12 | 119.4 |
C11—C10—C9 | 119.1 (2) | O2—C22—C21 | 116.8 (2) |
C11—C10—H10 | 120.4 | O3—C22—O2 | 126.7 (2) |
C19—C18—H18 | 119.9 | O3—C22—C21 | 116.5 (2) |
C17—C18—C19 | 120.1 (2) | C2—C3—H3 | 119.3 |
C17—C18—H18 | 119.9 | C2—C3—C4 | 121.4 (2) |
C1—C2—H2 | 120.5 | C4—C3—H3 | 119.3 |
C3—C2—C1 | 119.0 (2) | C5—C4—C3 | 120.7 (2) |
C3—C2—H2 | 120.5 | C5—C4—H4 | 119.6 |
C19—C14—H14 | 119.5 | C3—C4—H4 | 119.6 |
N1—C9—C8—C7 | 0.5 (3) | C20—C19—C14—C15 | −179.2 (2) |
N1—C9—C8—C13 | −179.72 (19) | C6—C1—C2—C3 | −0.5 (3) |
N1—C9—C10—C11 | 179.6 (2) | C6—C5—C4—C3 | −0.3 (4) |
N1—C1—C6—C7 | 0.7 (3) | C7—C8—C13—C12 | 179.8 (2) |
N1—C1—C6—C5 | −179.31 (18) | C7—C6—C5—C4 | 179.9 (2) |
N1—C1—C2—C3 | 179.3 (2) | C10—C9—C8—C7 | −179.22 (19) |
N2—C21—C22—O2 | 175.4 (2) | C10—C9—C8—C13 | 0.5 (3) |
N2—C21—C22—O3 | −4.7 (4) | C10—C11—C12—C13 | 0.5 (4) |
C9—N1—C1—C6 | −0.5 (3) | C18—C19—C20—N2 | 29.3 (3) |
C9—N1—C1—C2 | 179.65 (18) | C18—C19—C20—O1 | −149.9 (2) |
C9—C8—C7—C6 | −0.3 (3) | C18—C19—C14—C15 | −0.3 (3) |
C9—C8—C13—C12 | 0.1 (3) | C18—C17—C16—C15 | −1.1 (4) |
C9—C10—C11—C12 | 0.1 (3) | C2—C1—C6—C7 | −179.46 (19) |
C19—C18—C17—C16 | 2.0 (3) | C2—C1—C6—C5 | 0.5 (3) |
C19—C14—C15—C16 | 1.2 (4) | C2—C3—C4—C5 | 0.3 (4) |
C1—N1—C9—C8 | −0.1 (3) | C14—C19—C20—N2 | −151.83 (19) |
C1—N1—C9—C10 | 179.64 (19) | C14—C19—C20—O1 | 29.0 (3) |
C1—C6—C7—C8 | −0.3 (3) | C14—C19—C18—C17 | −1.3 (3) |
C1—C6—C5—C4 | −0.1 (3) | C14—C15—C16—C17 | −0.5 (4) |
C1—C2—C3—C4 | 0.1 (4) | C5—C6—C7—C8 | 179.7 (2) |
C8—C9—C10—C11 | −0.6 (3) | C21—N2—C20—O1 | −8.3 (3) |
C8—C13—C12—C11 | −0.6 (4) | C21—N2—C20—C19 | 172.53 (18) |
C20—N2—C21—C22 | −77.4 (3) | C13—C8—C7—C6 | 179.9 (2) |
C20—C19—C18—C17 | 177.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
Salt I | ||||
N1—H1A···O1 | 1.043 (18) | 1.549 (18) | 2.5879 (15) | 173 (2) |
N2—H2B···O1i | 0.99 (2) | 2.07 (2) | 3.0059 (19) | 158.5 (17) |
N2—H2B···O2ii | 0.87 (2) | 2.11 (2) | 2.9796 (18) | 171.4 (17) |
O3—H16···O2 | 0.93 (2) | 1.68 (2) | 2.556 (16) | 156 (2) |
C19—H19···O3iii | 1.004 (14) | 2.564 (15) | 3.3086 (16) | 130.8 (12) |
Salt II | ||||
N1—H1A···O1 | 0.86 | 1.80 | 2.641 (2) | 166 |
O3—H15···O2 | 0.82 | 1.78 | 2.507 (2) | 148 |
C2—H2···O2 | 0.93 | 2.57 | 3.236 (3) | 129 |
C11—H11···O3iv | 0.93 | 2.59 | 3.280 (3) | 131 |
C12—H12···O2 | 0.93 | 2.43 | 3.318 (2) | 160 |
Salt III | ||||
N1—H1···O3 | 0.86 | 1.72 | 2.545 (3) | 159 |
N2—H2A···O4iii | 0.86 | 2.13 | 2.878 (3) | 145 |
O4—H4A···O2 | 0.85 | 1.92 | 2.773 (3) | 177 |
O4—H4B···O2v | 0.85 | 1.97 | 2.815 (3) | 174 |
C7—H7···O4vi | 0.93 | 2.58 | 3.454 (3) | 157 |
C10—H10···O3 | 0.93 | 2.57 | 3.204 (3) | 25 |
C11—H11···O1vii | 0.93 | 2.53 | 3.369 (3) | 150 |
C17—H17···O1iii | 0.93 | 2.55 | 3.390 (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. |
D–H···A | H···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···O1 | 1.549 (18) | 0.478 | 3.399 | 0.148 | -0.260 | -0.112 | -0.130 | 341.47 |
O3—H16···O2 | 2.07 (2) | 0.343 | 3.752 | 0.097 | -0.156 | -0.058 | -0.078 | 204.48 |
Salt II | ||||||||
N1—H1A···O1 | 1.80 | 0.298 | 3.524 | 0.080 | -0.125 | -0.044 | -0.063 | 164.26 |
O3—H15···O2 | 1.78 | 0.484 | 3.866 | 0.154 | -0.267 | -0.113 | -0.133 | 350.42 |
Salt III | ||||||||
N1—H1···O3 | 0.86 | 0.383 | 4.282 | 0.115 | -0.186 | -0.07 | -0.093 | 244.73 |
N2—H2A···O4 | 0.86 | 0.151 | 2.249 | 0.034 | -0.044 | -0.01 | -0.022 | 57.92 |
Molecular descriptors | Salt I | Salt II | Salt III |
Energy (eV) | |||
Electron affinity A = [-ELUMO] | 3.598 | 3.951 | 3.630 |
Ionization potential I = [-EHOMO] | 4.597 | 4.994 | 4.567 |
Global hardness ν = (I - A)/2 | 0.500 | 0.522 | 0.469 |
Electrochemical potential µ =-(I + A)/2 | -4.098 | -4.473 | -4.099 |
Electrophilicity ω = µ2/2ν | 16.794 | 19.164 | 17.912 |
Electronegativity χ = (I + A)/2 | 4.098 | 4.473 | 4.099 |
HOMO energy | -4.597 | -4.994 | -4.567 |
LUMO energy | -3.598 | -3.951 | -3.630 |
Band gap =[ELUMO - EHUMO] | 0.999 | 1.043 | 0.937 |