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The crystal structures of the four isomeric organic salts 4-amino­pyridinium 2-chloro-4-nitro­benzoate, (I), 4-amino­pyridinium 2-chloro-5-nitro­benzoate, (II), 4-amino­pyridinium 5-chloro-2-nitro­benzoate, (III), and 4-amino­pyridinium 4-chloro-2-nitro­benzoate, (IV), all C5H7N2+·C7H3ClNO4, are presented. Compound (I) has one intramolecular hydrogen bond, one intermolecular C—H...O hydrogen bond and π–π-stacking interactions. Compound (II) has N—H...O, C—H...O and C—H...Cl hydrogen bonds, and Cl...O—C electrostatic interactions. Compound (III) has N—H...O and C—H...O hydrogen bonds. Compound (IV) has a π–π-stacking interaction, but no C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102003657/gd1189sup1.cif
Contains datablocks global, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003657/gd1189Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003657/gd1189IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003657/gd1189IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003657/gd1189IVsup5.hkl
Contains datablock IV

CCDC references: 184504; 184505; 184506; 184507

Computing details top

For all compounds, data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) 4-aminopyridium 2-chloro-4-nitrobenzoate top
Crystal data top
C5H7N2+·C7H3ClNO4F(000) = 1216
Mr = 295.68Dx = 1.520 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 9.923 (3) ŵ = 0.31 mm1
b = 9.527 (3) ÅT = 293 K
c = 27.337 (7) ÅPrism, colourless
V = 2584.5 (12) Å30.30 × 0.25 × 0.20 mm
Z = 8
Data collection top
Make? Model? CCD area-detector
diffractometer
2288 independent reflections
Radiation source: fine-focus sealed tube1249 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)
h = 1111
Tmin = 0.912, Tmax = 0.940k = 119
10028 measured reflectionsl = 2732
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
2288 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.85111 (8)0.00988 (11)0.42905 (3)0.0568 (3)
O10.4469 (2)0.2117 (3)0.40453 (7)0.0559 (7)
O20.6346 (3)0.1315 (3)0.37250 (8)0.0632 (8)
O30.6486 (3)0.1049 (3)0.64008 (9)0.0675 (8)
O40.8201 (3)0.0147 (3)0.61549 (9)0.0617 (8)
N10.8181 (3)0.3445 (4)0.33471 (10)0.0656 (10)
H1A0.85440.41560.34890.079*
H1B0.76260.29200.35050.079*
N30.7211 (3)0.0585 (3)0.60780 (10)0.0482 (8)
C10.8479 (3)0.3153 (4)0.28809 (12)0.0449 (9)
C20.7873 (4)0.2023 (4)0.26399 (12)0.0549 (10)
H2A0.72890.14340.28090.066*
C30.8130 (4)0.1782 (4)0.21645 (13)0.0619 (11)
H3A0.77070.10350.20090.074*
N20.8976 (3)0.2589 (4)0.19116 (11)0.0593 (9)
H2B0.91260.24190.16070.071*
C40.9590 (4)0.3661 (5)0.21320 (13)0.0631 (12)
H4A1.01860.42110.19530.076*
C50.9373 (3)0.3973 (4)0.26093 (12)0.0577 (11)
H5A0.98160.47270.27540.069*
C60.5629 (3)0.1615 (3)0.40773 (11)0.0359 (8)
C70.6145 (3)0.1374 (3)0.45960 (11)0.0312 (7)
C80.7343 (3)0.0689 (3)0.47179 (11)0.0349 (8)
C90.7686 (3)0.0434 (4)0.52034 (11)0.0388 (9)
H9A0.84710.00500.52810.047*
C100.6850 (3)0.0907 (4)0.55653 (10)0.0370 (8)
C110.5685 (3)0.1631 (4)0.54680 (11)0.0418 (9)
H11A0.51410.19650.57190.050*
C120.5352 (3)0.1845 (3)0.49861 (11)0.0401 (9)
H12A0.45600.23260.49160.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0519 (6)0.0777 (8)0.0406 (5)0.0161 (5)0.0030 (4)0.0075 (5)
O10.0558 (15)0.080 (2)0.0324 (14)0.0197 (15)0.0096 (12)0.0038 (12)
O20.0723 (17)0.092 (2)0.0250 (13)0.0244 (16)0.0033 (12)0.0009 (13)
O30.0739 (18)0.100 (2)0.0288 (14)0.0006 (17)0.0039 (13)0.0022 (14)
O40.0658 (18)0.077 (2)0.0425 (15)0.0048 (16)0.0174 (13)0.0173 (14)
N10.079 (2)0.086 (3)0.0318 (17)0.017 (2)0.0108 (16)0.0218 (16)
N30.056 (2)0.059 (2)0.0298 (17)0.0160 (17)0.0084 (16)0.0083 (15)
C10.044 (2)0.059 (3)0.032 (2)0.0078 (19)0.0025 (16)0.0078 (18)
C20.073 (3)0.053 (3)0.039 (2)0.003 (2)0.0089 (19)0.0063 (18)
C30.085 (3)0.061 (3)0.039 (2)0.013 (2)0.002 (2)0.011 (2)
N20.063 (2)0.084 (3)0.0312 (17)0.026 (2)0.0051 (16)0.0070 (18)
C40.049 (2)0.095 (4)0.045 (2)0.004 (2)0.0069 (19)0.007 (2)
C50.053 (2)0.078 (3)0.042 (2)0.011 (2)0.0022 (19)0.007 (2)
C60.044 (2)0.034 (2)0.0293 (19)0.0014 (17)0.0037 (16)0.0029 (15)
C70.0383 (18)0.0278 (19)0.0275 (17)0.0039 (15)0.0020 (14)0.0011 (14)
C80.0389 (18)0.036 (2)0.0293 (18)0.0034 (16)0.0023 (14)0.0017 (15)
C90.0360 (18)0.044 (2)0.037 (2)0.0011 (16)0.0065 (16)0.0040 (16)
C100.0460 (19)0.040 (2)0.0246 (17)0.0086 (17)0.0055 (15)0.0071 (15)
C110.050 (2)0.048 (2)0.0279 (19)0.0005 (18)0.0044 (16)0.0003 (15)
C120.048 (2)0.040 (2)0.0327 (19)0.0080 (17)0.0003 (16)0.0045 (16)
Geometric parameters (Å, º) top
Cl1—C81.739 (3)N2—H2B0.8600
O1—C61.250 (4)C4—C51.356 (5)
O2—C61.231 (4)C4—H4A0.9300
O3—N31.221 (4)C5—H5A0.9300
O4—N31.223 (3)C6—O21.231 (4)
N1—C11.338 (4)C6—O11.250 (4)
N1—H1A0.8600C6—C71.525 (4)
N1—H1B0.8600C7—C81.396 (4)
N3—C101.479 (4)C7—C121.399 (4)
C1—C51.396 (5)C8—C91.392 (4)
C1—C21.398 (5)C9—C101.368 (4)
C2—C31.344 (5)C9—H9A0.9300
C2—H2A0.9300C10—C111.372 (4)
C3—N21.331 (5)C11—C121.374 (4)
C3—H3A0.9300C11—H11A0.9300
N2—C41.333 (5)C12—H12A0.9300
C1—N1—H1A120.0O2—C6—O1124.5 (3)
C1—N1—H1B120.0O2—C6—O1124.5 (3)
H1A—N1—H1B120.0O2—C6—O1124.5 (3)
O3—N3—O4123.8 (3)O2—C6—C7119.9 (3)
O3—N3—C10117.8 (3)O2—C6—C7119.9 (3)
O4—N3—C10118.4 (3)O1—C6—C7115.6 (3)
N1—C1—C5122.1 (3)O1—C6—C7115.6 (3)
N1—C1—C2120.9 (3)C8—C7—C12116.5 (3)
C5—C1—C2117.0 (3)C8—C7—C6125.3 (3)
C3—C2—C1120.3 (4)C12—C7—C6118.2 (3)
C3—C2—H2A119.8C9—C8—C7121.2 (3)
C1—C2—H2A119.8C9—C8—Cl1114.9 (2)
N2—C3—C2121.6 (4)C7—C8—Cl1123.9 (2)
N2—C3—H3A119.2C10—C9—C8118.9 (3)
C2—C3—H3A119.2C10—C9—H9A120.5
C3—N2—C4119.7 (3)C8—C9—H9A120.5
C3—N2—H2B120.1C9—C10—C11122.4 (3)
C4—N2—H2B120.1C9—C10—N3118.0 (3)
N2—C4—C5122.1 (4)C11—C10—N3119.5 (3)
N2—C4—H4A119.0C10—C11—C12117.6 (3)
C5—C4—H4A119.0C10—C11—H11A121.2
C4—C5—C1119.3 (4)C12—C11—H11A121.2
C4—C5—H5A120.3C11—C12—C7123.3 (3)
C1—C5—H5A120.3C11—C12—H12A118.4
O2—C6—O1124.5 (3)C7—C12—H12A118.4
N1—C1—C2—C3176.7 (4)O1—C6—C7—C125.8 (4)
C5—C1—C2—C31.7 (5)O1—C6—C7—C125.8 (4)
C1—C2—C3—N21.0 (6)C12—C7—C8—C93.0 (5)
C2—C3—N2—C40.2 (6)C6—C7—C8—C9175.6 (3)
C3—N2—C4—C50.6 (6)C12—C7—C8—Cl1176.8 (2)
N2—C4—C5—C10.1 (6)C6—C7—C8—Cl14.6 (5)
N1—C1—C5—C4177.2 (4)C7—C8—C9—C102.1 (5)
C2—C1—C5—C41.2 (5)Cl1—C8—C9—C10177.7 (3)
O2—O2—C6—O10.0 (3)C8—C9—C10—C110.3 (5)
O2—O2—C6—O10.0 (3)C8—C9—C10—N3178.1 (3)
O2—O2—C6—C70.0 (4)O3—N3—C10—C9177.6 (3)
O1—O1—C6—O20.00 (13)O4—N3—C10—C93.5 (5)
O1—O1—C6—O20.00 (13)O3—N3—C10—C114.0 (5)
O1—O1—C6—C70.00 (13)O4—N3—C10—C11174.9 (3)
O2—C6—C7—C87.1 (5)C9—C10—C11—C121.7 (5)
O2—C6—C7—C87.1 (5)N3—C10—C11—C12176.7 (3)
O1—C6—C7—C8172.7 (3)C10—C11—C12—C70.6 (5)
O1—C6—C7—C8172.7 (3)C8—C7—C12—C111.7 (5)
O2—C6—C7—C12174.3 (3)C6—C7—C12—C11177.0 (3)
O2—C6—C7—C12174.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O20.862.082.915 (4)165
N1—H1A···O2i0.862.162.961 (4)155
N2—H2B···O1ii0.861.842.699 (3)178
C3—H3A···O4iii0.932.643.434 (5)144
C12—H12A···O10.932.392.729 (4)101
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+1/2, y, z+1/2; (iii) x+3/2, y, z1/2.
(II) 4-Aminopyridium 2-chloro-5-nitrobenzoate top
Crystal data top
C5H7N2+·C7H3ClNO4Z = 4
Mr = 295.68F(000) = 608
Monoclinic, P21/nDx = 1.535 Mg m3
a = 12.624 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.270 (2) ŵ = 0.32 mm1
c = 14.023 (5) ÅT = 293 K
β = 96.329 (5)°Prism, colourless
V = 1279.1 (7) Å30.35 × 0.30 × 0.25 mm
Data collection top
Make? Model? CCD area-detector
diffractometer
2256 independent reflections
Radiation source: fine-focus sealed tube1660 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)
h = 1415
Tmin = 0.897, Tmax = 0.925k = 84
5062 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.05P)2 + 0.08P]
where P = (Fo2 + 2Fc2)/3
2256 reflections(Δ/σ)max = 0.026
193 parametersΔρmax = 0.15 e Å3
3 restraintsΔρmin = 0.23 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.01449 (4)0.13515 (8)0.11788 (4)0.04517 (18)
O10.83406 (12)0.1551 (2)0.05023 (10)0.0534 (4)
O20.69773 (11)0.0320 (2)0.06848 (10)0.0510 (4)
O30.67868 (12)0.0782 (2)0.43183 (10)0.0533 (4)
O40.82083 (13)0.0220 (3)0.52749 (10)0.0719 (6)
N10.54346 (17)0.1523 (3)0.39945 (13)0.0520 (5)
H20.5928 (17)0.134 (4)0.4396 (16)0.081 (9)*
H10.4803 (12)0.206 (3)0.4148 (17)0.073 (8)*
N20.63461 (15)0.0477 (3)0.11447 (12)0.0472 (5)
H30.656 (2)0.032 (4)0.0501 (8)0.080 (8)*
C10.57376 (16)0.1142 (3)0.30697 (14)0.0382 (5)
C20.50241 (16)0.1369 (3)0.23733 (14)0.0399 (5)
H2A0.43290.17540.25560.048*
N30.77181 (14)0.0301 (3)0.44713 (12)0.0454 (5)
C30.53540 (18)0.1024 (3)0.14320 (15)0.0444 (5)
H3A0.48760.11750.09790.053*
C40.70447 (18)0.0222 (3)0.17941 (16)0.0542 (6)
H4A0.77330.01670.15850.065*
C50.67689 (17)0.0517 (3)0.27428 (16)0.0499 (6)
H5A0.72610.03070.31780.060*
C60.78649 (16)0.0405 (3)0.09499 (13)0.0357 (5)
C70.83698 (14)0.0160 (3)0.19436 (13)0.0317 (4)
C80.78180 (15)0.0196 (3)0.27315 (13)0.0341 (5)
H8A0.71350.06890.26410.041*
C90.82873 (15)0.0184 (3)0.36465 (13)0.0358 (5)
C100.92851 (17)0.0979 (3)0.38164 (14)0.0417 (5)
H10A0.95780.12520.44380.050*
C110.98389 (16)0.1361 (3)0.30403 (14)0.0396 (5)
H11A1.05090.19070.31350.047*
C120.93874 (15)0.0925 (3)0.21184 (13)0.0340 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0388 (3)0.0564 (4)0.0414 (3)0.0021 (2)0.0093 (2)0.0090 (3)
O10.0503 (9)0.0663 (11)0.0421 (8)0.0106 (8)0.0013 (7)0.0153 (8)
O20.0401 (9)0.0727 (11)0.0374 (8)0.0110 (8)0.0084 (7)0.0068 (7)
O30.0469 (10)0.0672 (11)0.0476 (9)0.0109 (8)0.0135 (8)0.0003 (8)
O40.0607 (11)0.1253 (17)0.0285 (9)0.0042 (11)0.0002 (8)0.0081 (9)
N10.0528 (13)0.0674 (14)0.0354 (10)0.0090 (11)0.0027 (9)0.0064 (9)
N20.0458 (12)0.0585 (12)0.0349 (10)0.0080 (9)0.0056 (9)0.0021 (9)
C10.0407 (12)0.0374 (11)0.0353 (11)0.0036 (9)0.0003 (9)0.0005 (9)
C20.0350 (11)0.0421 (12)0.0417 (12)0.0053 (9)0.0003 (9)0.0022 (10)
N30.0472 (12)0.0552 (12)0.0344 (10)0.0022 (9)0.0063 (9)0.0017 (8)
C30.0455 (13)0.0485 (13)0.0393 (12)0.0012 (10)0.0057 (10)0.0010 (10)
C40.0329 (12)0.0730 (17)0.0545 (15)0.0020 (12)0.0055 (11)0.0093 (12)
C50.0375 (12)0.0682 (16)0.0448 (13)0.0004 (11)0.0080 (10)0.0043 (11)
C60.0338 (11)0.0428 (12)0.0302 (10)0.0045 (10)0.0021 (9)0.0032 (9)
C70.0322 (10)0.0331 (11)0.0291 (10)0.0043 (8)0.0001 (8)0.0020 (8)
C80.0294 (10)0.0377 (11)0.0347 (10)0.0004 (9)0.0012 (8)0.0005 (9)
C90.0365 (11)0.0410 (12)0.0300 (10)0.0013 (9)0.0035 (9)0.0013 (9)
C100.0439 (12)0.0484 (13)0.0311 (10)0.0026 (10)0.0034 (9)0.0033 (9)
C110.0333 (11)0.0413 (12)0.0424 (11)0.0070 (9)0.0031 (9)0.0009 (10)
C120.0321 (11)0.0350 (11)0.0346 (10)0.0023 (8)0.0021 (9)0.0053 (9)
Geometric parameters (Å, º) top
Cl1—C121.7390 (19)C3—H3A0.9300
O1—C61.237 (2)C4—C51.355 (3)
O2—C61.257 (2)C4—H4A0.9300
O3—N31.223 (2)C5—H5A0.9300
O4—N31.226 (2)C6—O21.257 (2)
N1—C11.340 (3)C6—C71.524 (3)
N1—H20.894 (10)C7—C81.394 (3)
N1—H10.892 (10)C7—C121.397 (3)
N2—C31.334 (3)C8—C91.381 (3)
N2—C41.349 (3)C8—H8A0.9300
N2—H30.920 (10)C9—C101.383 (3)
C1—C51.407 (3)C10—C111.385 (3)
C1—C21.409 (3)C10—H10A0.9300
C2—C31.363 (3)C11—C121.391 (3)
C2—H2A0.9300C11—H11A0.9300
N3—C91.470 (3)
C1—N1—H2115.8 (18)O1—C6—O2126.80 (18)
C1—N1—H1118.4 (16)O1—C6—O2126.80 (18)
H2—N1—H1125 (3)O1—C6—C7117.91 (17)
C3—N2—C4119.96 (18)O2—C6—C7115.26 (17)
C3—N2—H3120.0 (16)O2—C6—C7115.26 (17)
C4—N2—H3120.0 (16)C8—C7—C12117.74 (17)
N1—C1—C5122.49 (19)C8—C7—C6118.66 (17)
N1—C1—C2120.69 (19)C12—C7—C6123.49 (16)
C5—C1—C2116.82 (18)C9—C8—C7119.91 (17)
C3—C2—C1119.94 (19)C9—C8—H8A120.0
C3—C2—H2A120.0C7—C8—H8A120.0
C1—C2—H2A120.0C8—C9—C10122.23 (17)
O3—N3—O4123.58 (17)C8—C9—N3119.10 (17)
O3—N3—C9118.33 (17)C10—C9—N3118.66 (17)
O4—N3—C9118.09 (18)C9—C10—C11118.54 (18)
N2—C3—C2121.60 (19)C9—C10—H10A120.7
N2—C3—H3A119.2C11—C10—H10A120.7
C2—C3—H3A119.2C10—C11—C12119.60 (18)
N2—C4—C5121.7 (2)C10—C11—H11A120.2
N2—C4—H4A119.2C12—C11—H11A120.2
C5—C4—H4A119.2C11—C12—C7121.92 (17)
C4—C5—C1120.0 (2)C11—C12—Cl1117.41 (15)
C4—C5—H5A120.0C7—C12—Cl1120.67 (14)
C1—C5—H5A120.0
N1—C1—C2—C3178.2 (2)C6—C7—C8—C9175.51 (18)
C5—C1—C2—C31.4 (3)C7—C8—C9—C102.4 (3)
C4—N2—C3—C21.1 (3)C7—C8—C9—N3176.48 (17)
C1—C2—C3—N20.2 (3)O3—N3—C9—C810.2 (3)
C3—N2—C4—C50.3 (4)O4—N3—C9—C8168.88 (19)
N2—C4—C5—C11.3 (4)O3—N3—C9—C10170.81 (19)
N1—C1—C5—C4177.4 (2)O4—N3—C9—C1010.1 (3)
C2—C1—C5—C42.1 (3)C8—C9—C10—C111.7 (3)
O2—O2—C6—O10.00 (5)N3—C9—C10—C11177.26 (18)
O2—O2—C6—C70.00 (4)C9—C10—C11—C120.6 (3)
O1—C6—C7—C8118.1 (2)C10—C11—C12—C72.1 (3)
O2—C6—C7—C859.8 (2)C10—C11—C12—Cl1177.41 (16)
O2—C6—C7—C859.8 (2)C8—C7—C12—C111.3 (3)
O1—C6—C7—C1258.1 (3)C6—C7—C12—C11177.55 (18)
O2—C6—C7—C12124.1 (2)C8—C7—C12—Cl1178.16 (14)
O2—C6—C7—C12124.1 (2)C6—C7—C12—Cl12.0 (3)
C12—C7—C8—C90.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.89 (1)2.12 (1)3.006 (3)177 (2)
N1—H2···O3ii0.89 (1)2.24 (1)3.113 (2)165 (2)
N2—H3···O20.92 (1)1.75 (1)2.665 (2)172 (2)
C5—H5A···O4ii0.932.593.491 (3)163
C3—H3A···O2iii0.932.503.271 (3)141
C4—H4A···Cl1iv0.932.903.651 (2)139
Symmetry codes: (i) x1/2, y1/2, z1/2; (ii) x, y, z1; (iii) x+1, y, z; (iv) x+2, y, z.
(III) 4-Aminopyridium 5-chloro-2-nitrobenzoate top
Crystal data top
C5H7N2+·C7H3ClNO4Z = 4
Mr = 295.68F(000) = 608
Monoclinic, P21/cDx = 1.533 Mg m3
a = 12.219 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.488 (4) ŵ = 0.32 mm1
c = 13.368 (6) ÅT = 293 K
β = 112.467 (9)°Prism, colourless
V = 1281.1 (10) Å30.30 × 0.25 × 0.20 mm
Data collection top
Make? Model? CCD area-detector
diffractometer
2255 independent reflections
Radiation source: fine-focus sealed tube1174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)
h = 1410
Tmin = 0.911, Tmax = 0.940k = 109
5126 measured reflectionsl = 1015
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0656P)2]
where P = (Fo2 + 2Fc2)/3
2255 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.08960 (10)0.22145 (13)0.03102 (10)0.0649 (4)
N10.8009 (3)0.4187 (4)0.2138 (3)0.0475 (9)
N20.5951 (3)0.1550 (4)0.0908 (3)0.0472 (10)
H10.586 (3)0.075 (5)0.070 (3)0.048 (14)*
N30.6563 (3)0.5932 (4)0.1812 (3)0.0454 (9)
H30.674 (3)0.592 (5)0.244 (3)0.060 (13)*
H20.652 (4)0.663 (5)0.140 (3)0.062 (16)*
O10.6377 (2)0.1612 (3)0.0350 (2)0.0440 (7)
O20.7186 (3)0.0543 (3)0.1294 (2)0.0616 (8)
O30.6973 (3)0.3825 (3)0.1829 (2)0.0648 (9)
O40.8469 (3)0.5061 (4)0.2911 (3)0.0923 (12)
C10.7172 (4)0.1468 (4)0.0573 (3)0.0402 (9)
C20.8297 (3)0.2433 (4)0.0798 (3)0.0364 (9)
C30.8992 (3)0.2036 (4)0.0227 (3)0.0414 (9)
H3A0.87240.12740.03120.050*
C41.0068 (4)0.2740 (4)0.0440 (3)0.0461 (10)
C51.0500 (4)0.3880 (5)0.1227 (4)0.0539 (11)
H5A1.12340.43450.13730.065*
C60.9815 (4)0.4307 (5)0.1790 (3)0.0514 (11)
H6A1.00830.50750.23260.062*
C70.8735 (3)0.3606 (4)0.1567 (3)0.0382 (9)
C80.5864 (3)0.2796 (5)0.0325 (3)0.0472 (10)
H8A0.56800.26460.02820.057*
C90.6043 (3)0.4270 (4)0.0617 (3)0.0397 (9)
H9A0.59780.51320.02140.048*
C100.6326 (3)0.4493 (4)0.1526 (3)0.0345 (9)
C110.6376 (3)0.3156 (4)0.2124 (3)0.0433 (10)
H11A0.65310.32600.27510.052*
C120.6199 (3)0.1724 (5)0.1784 (3)0.0468 (11)
H12A0.62510.08360.21720.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0541 (7)0.0647 (7)0.0901 (9)0.0088 (6)0.0433 (6)0.0117 (6)
N10.057 (3)0.0383 (19)0.046 (2)0.0003 (18)0.0178 (19)0.0063 (17)
N20.039 (2)0.030 (2)0.069 (3)0.0003 (16)0.0174 (19)0.012 (2)
N30.054 (2)0.034 (2)0.051 (2)0.0028 (17)0.0233 (19)0.0047 (19)
O10.0434 (17)0.0328 (14)0.0554 (18)0.0061 (12)0.0184 (15)0.0042 (13)
O20.084 (2)0.0533 (17)0.0575 (19)0.0168 (16)0.0379 (17)0.0018 (15)
O30.058 (2)0.068 (2)0.078 (2)0.0112 (17)0.0366 (18)0.0237 (17)
O40.081 (3)0.112 (3)0.079 (2)0.014 (2)0.025 (2)0.056 (2)
C10.053 (3)0.026 (2)0.050 (3)0.0039 (18)0.030 (2)0.006 (2)
C20.043 (2)0.0288 (19)0.037 (2)0.0012 (17)0.0145 (18)0.0031 (17)
C30.046 (3)0.034 (2)0.045 (2)0.0013 (19)0.0184 (19)0.0026 (18)
C40.039 (2)0.040 (2)0.058 (3)0.010 (2)0.018 (2)0.015 (2)
C50.033 (2)0.046 (3)0.076 (3)0.004 (2)0.012 (2)0.006 (2)
C60.046 (3)0.038 (2)0.061 (3)0.004 (2)0.009 (2)0.003 (2)
C70.046 (3)0.031 (2)0.037 (2)0.0031 (18)0.0157 (19)0.0035 (18)
C80.042 (2)0.052 (3)0.052 (3)0.005 (2)0.023 (2)0.011 (2)
C90.044 (2)0.031 (2)0.050 (2)0.0037 (18)0.0248 (19)0.0017 (19)
C100.027 (2)0.029 (2)0.044 (2)0.0022 (16)0.0097 (17)0.0004 (17)
C110.045 (3)0.044 (2)0.043 (2)0.0082 (18)0.0199 (19)0.0077 (19)
C120.044 (3)0.037 (2)0.061 (3)0.0053 (18)0.022 (2)0.012 (2)
Geometric parameters (Å, º) top
Cl1—C41.733 (4)C3—C41.372 (5)
N1—O31.211 (4)C3—H3A0.9300
N1—O41.220 (4)C4—C51.378 (5)
N1—C71.460 (5)C5—C61.372 (6)
N2—C121.325 (5)C5—H5A0.9300
N2—C81.342 (5)C6—C71.372 (5)
N2—H10.76 (4)C6—H6A0.9300
N3—C101.344 (4)C8—C91.353 (5)
N3—H30.94 (4)C8—H8A0.9300
N3—H20.82 (4)C9—C101.397 (5)
O1—C11.251 (4)C9—H9A0.9300
O2—C11.238 (4)C10—C111.404 (5)
C1—O11.251 (4)C11—C121.344 (5)
C1—C21.528 (5)C11—H11A0.9300
C2—C31.383 (5)C12—H12A0.9300
C2—C71.383 (5)
O3—N1—O4121.7 (4)C6—C5—H5A121.0
O3—N1—C7120.1 (3)C4—C5—H5A121.0
O4—N1—C7118.2 (4)C7—C6—C5120.2 (4)
C12—N2—C8121.4 (4)C7—C6—H6A119.9
C12—N2—H1122 (3)C5—C6—H6A119.9
C8—N2—H1116 (3)C6—C7—C2122.8 (4)
C10—N3—H3113 (2)C6—C7—N1117.8 (3)
C10—N3—H2113 (3)C2—C7—N1119.4 (4)
H3—N3—H2134 (4)N2—C8—C9120.2 (4)
O2—C1—O1127.2 (4)N2—C8—H8A119.9
O2—C1—O1127.2 (4)C9—C8—H8A119.9
O2—C1—C2116.3 (4)C8—C9—C10119.8 (4)
O1—C1—C2116.3 (3)C8—C9—H9A120.1
O1—C1—C2116.3 (3)C10—C9—H9A120.1
C3—C2—C7116.2 (4)N3—C10—C9121.5 (4)
C3—C2—C1117.1 (3)N3—C10—C11120.7 (4)
C7—C2—C1126.6 (3)C9—C10—C11117.7 (3)
C4—C3—C2121.4 (4)C12—C11—C10119.4 (4)
C4—C3—H3A119.3C12—C11—H11A120.3
C2—C3—H3A119.3C10—C11—H11A120.3
C3—C4—C5121.5 (4)N2—C12—C11121.4 (4)
C3—C4—Cl1119.5 (3)N2—C12—H12A119.3
C5—C4—Cl1119.0 (3)C11—C12—H12A119.3
C6—C5—C4117.9 (4)
O1—O1—C1—O20.00 (9)C3—C2—C7—C62.4 (5)
O1—O1—C1—C20.00 (6)C1—C2—C7—C6173.3 (4)
O2—C1—C2—C3107.8 (4)C3—C2—C7—N1174.8 (3)
O1—C1—C2—C366.8 (4)C1—C2—C7—N19.5 (5)
O1—C1—C2—C366.8 (4)O3—N1—C7—C6166.1 (3)
O2—C1—C2—C767.8 (5)O4—N1—C7—C612.4 (5)
O1—C1—C2—C7117.5 (4)O3—N1—C7—C211.3 (5)
O1—C1—C2—C7117.5 (4)O4—N1—C7—C2170.2 (3)
C7—C2—C3—C41.9 (5)C12—N2—C8—C90.8 (6)
C1—C2—C3—C4174.3 (3)N2—C8—C9—C100.3 (6)
C2—C3—C4—C50.4 (6)C8—C9—C10—N3176.9 (3)
C2—C3—C4—Cl1179.3 (3)C8—C9—C10—C112.0 (5)
C3—C4—C5—C60.6 (6)N3—C10—C11—C12176.4 (4)
Cl1—C4—C5—C6178.2 (3)C9—C10—C11—C122.5 (5)
C4—C5—C6—C70.1 (6)C8—N2—C12—C110.2 (6)
C5—C6—C7—C21.5 (6)C10—C11—C12—N21.5 (6)
C5—C6—C7—N1175.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H2···O1i0.82 (4)2.10 (4)2.925 (5)178 (4)
N2—H1···O10.76 (4)2.10 (4)2.781 (5)150 (4)
N3—H3···O2ii0.94 (4)2.00 (4)2.928 (5)171 (4)
C3—H3A···O4iii0.932.543.414 (5)156
C12—H12A···O3iii0.932.523.424 (5)163
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, z1/2; (iii) x, y+1/2, z1/2.
(IV) 4-Aminopyridium 4-chloro-2-nitrobenzoate top
Crystal data top
C5H7N2+·C7H3ClNO4Z = 8
Mr = 295.68F(000) = 1216
Monoclinic, C2/cDx = 1.499 Mg m3
a = 25.608 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.475 (6) ŵ = 0.31 mm1
c = 12.433 (10) ÅT = 293 K
β = 103.749 (14)°Prism, colourless
V = 2621 (3) Å30.30 × 0.25 × 0.20 mm
Data collection top
Make? Model? CCD area-detector
diffractometer
2308 independent reflections
Radiation source: fine-focus sealed tube1579 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1995)
h = 3026
Tmin = 0.913, Tmax = 0.941k = 109
5262 measured reflectionsl = 1412
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) = 0.120 w = 1/[σ2(Fo2) + (0.0586P)2 + 1.1026P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2308 reflectionsΔρmax = 0.23 e Å3
194 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (7)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.46273 (3)0.19463 (9)1.09806 (7)0.0691 (3)
O10.67956 (8)0.5915 (2)1.03009 (16)0.0627 (6)
O20.64006 (7)0.5301 (2)0.85667 (16)0.0623 (6)
O30.64154 (9)0.1909 (3)0.86890 (18)0.0766 (7)
O40.56335 (9)0.2125 (3)0.76201 (18)0.0929 (9)
N10.67789 (10)0.7470 (3)0.73599 (19)0.0543 (6)
H10.6714 (13)0.672 (4)0.785 (3)0.087 (11)*
N20.71828 (11)1.0873 (3)0.5373 (2)0.0553 (7)
H220.7050 (12)1.173 (3)0.530 (2)0.052 (9)*
H210.7497 (13)1.077 (3)0.510 (2)0.076 (10)*
N30.59496 (10)0.2314 (3)0.84955 (19)0.0499 (6)
C10.72010 (12)0.7263 (3)0.6911 (2)0.0545 (7)
H1A0.73990.63340.70520.065*
C20.73461 (10)0.8376 (3)0.6258 (2)0.0475 (7)
H2A0.76450.82130.59700.057*
C30.70500 (9)0.9766 (3)0.6015 (2)0.0405 (6)
C40.66046 (10)0.9934 (3)0.6484 (2)0.0500 (7)
H4A0.63911.08320.63410.060*
C50.64896 (11)0.8785 (4)0.7142 (2)0.0574 (8)
H5A0.61970.89180.74560.069*
C60.51680 (10)0.2849 (3)1.0603 (2)0.0440 (6)
C70.54252 (10)0.4093 (3)1.1214 (2)0.0472 (7)
H7A0.53180.44391.18380.057*
C80.58457 (10)0.4825 (3)1.0888 (2)0.0437 (6)
H8A0.60160.56771.12970.052*
C90.60195 (9)0.4326 (3)0.99716 (18)0.0361 (6)
C100.57535 (9)0.3041 (3)0.94051 (19)0.0377 (6)
C110.53250 (10)0.2298 (3)0.9689 (2)0.0435 (6)
H11A0.51490.14560.92760.052*
C120.64452 (10)0.5254 (3)0.9582 (2)0.0430 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0676 (5)0.0614 (5)0.0935 (7)0.0098 (4)0.0490 (4)0.0062 (4)
O10.0603 (13)0.0647 (12)0.0681 (13)0.0248 (10)0.0255 (10)0.0151 (11)
O20.0682 (13)0.0773 (13)0.0494 (12)0.0148 (11)0.0299 (9)0.0101 (10)
O30.0678 (15)0.0954 (17)0.0710 (15)0.0281 (12)0.0255 (11)0.0145 (12)
O40.0675 (15)0.162 (3)0.0502 (13)0.0161 (15)0.0163 (11)0.0370 (15)
N10.0667 (16)0.0543 (14)0.0447 (14)0.0130 (13)0.0190 (12)0.0040 (12)
N20.0563 (16)0.0445 (14)0.0714 (17)0.0042 (12)0.0278 (13)0.0142 (12)
N30.0552 (15)0.0565 (14)0.0418 (13)0.0058 (12)0.0191 (11)0.0076 (11)
C10.0603 (18)0.0512 (16)0.0517 (17)0.0056 (14)0.0125 (14)0.0093 (14)
C20.0431 (14)0.0503 (15)0.0520 (16)0.0047 (12)0.0173 (12)0.0057 (13)
C30.0396 (14)0.0402 (13)0.0424 (14)0.0045 (11)0.0114 (11)0.0023 (11)
C40.0448 (15)0.0465 (15)0.0631 (18)0.0012 (12)0.0213 (13)0.0025 (13)
C50.0530 (17)0.0678 (19)0.0595 (18)0.0126 (15)0.0298 (14)0.0105 (16)
C60.0434 (15)0.0423 (14)0.0524 (16)0.0027 (11)0.0233 (12)0.0105 (12)
C70.0568 (16)0.0485 (15)0.0445 (15)0.0041 (13)0.0284 (12)0.0013 (12)
C80.0533 (16)0.0408 (14)0.0399 (14)0.0009 (12)0.0170 (11)0.0030 (11)
C90.0371 (13)0.0379 (13)0.0354 (13)0.0026 (11)0.0126 (10)0.0046 (11)
C100.0421 (14)0.0397 (13)0.0339 (13)0.0047 (11)0.0142 (10)0.0031 (11)
C110.0435 (15)0.0392 (14)0.0489 (15)0.0020 (11)0.0129 (11)0.0013 (11)
C120.0462 (15)0.0370 (13)0.0523 (16)0.0021 (12)0.0247 (13)0.0040 (13)
Geometric parameters (Å, º) top
Cl1—C61.742 (3)C2—H2A0.9300
O1—C121.240 (3)C3—C41.406 (3)
O2—C121.241 (3)C4—C51.349 (4)
O3—N31.209 (3)C4—H4A0.9300
O4—N31.203 (3)C5—H5A0.9300
N1—C51.330 (4)C6—C71.372 (4)
N1—C11.340 (4)C6—C111.374 (3)
N1—H10.93 (3)C7—C81.384 (3)
N2—C31.327 (3)C7—H7A0.9300
N2—H220.80 (3)C8—C91.385 (3)
N2—H210.95 (3)C8—H8A0.9300
N3—C101.477 (3)C9—C101.384 (3)
C1—C21.353 (4)C9—C121.514 (3)
C1—H1A0.9300C10—C111.382 (3)
C2—C31.394 (4)C11—H11A0.9300
C5—N1—C1119.4 (2)C4—C5—H5A118.8
C5—N1—H1122 (2)C7—C6—C11121.5 (2)
C1—N1—H1118 (2)C7—C6—Cl1119.7 (2)
C3—N2—H22123 (2)C11—C6—Cl1118.8 (2)
C3—N2—H21121.0 (18)C6—C7—C8119.2 (2)
H22—N2—H21115 (3)C6—C7—H7A120.4
O4—N3—O3124.2 (2)C8—C7—H7A120.4
O4—N3—C10118.1 (2)C7—C8—C9121.9 (2)
O3—N3—C10117.7 (2)C7—C8—H8A119.1
N1—C1—C2121.5 (3)C9—C8—H8A119.1
N1—C1—H1A119.3C10—C9—C8116.3 (2)
C2—C1—H1A119.3C10—C9—C12123.4 (2)
C1—C2—C3120.4 (2)C8—C9—C12120.1 (2)
C1—C2—H2A119.8C11—C10—C9123.6 (2)
C3—C2—H2A119.8C11—C10—N3116.1 (2)
N2—C3—C2121.6 (2)C9—C10—N3120.1 (2)
N2—C3—C4121.8 (3)C6—C11—C10117.5 (2)
C2—C3—C4116.6 (2)C6—C11—H11A121.2
C5—C4—C3119.6 (3)C10—C11—H11A121.2
C5—C4—H4A120.2O1—C12—O2126.5 (2)
C3—C4—H4A120.2O1—C12—C9117.2 (2)
N1—C5—C4122.5 (3)O2—C12—C9116.3 (2)
N1—C5—H5A118.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.93 (3)1.79 (3)2.694 (3)164 (3)
N2—H22···O1i0.80 (3)2.10 (3)2.891 (4)172 (3)
N2—H21···O1ii0.95 (3)1.99 (3)2.931 (4)169 (3)
Symmetry codes: (i) x, y+2, z1/2; (ii) x+3/2, y+1/2, z+3/2.
 

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