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 C
5H
7N
2+·C
7H
3ClNO
4−, 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
CCDC references: 184504; 184505; 184506; 184507
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+·C7H3ClNO4− | F(000) = 1216 |
Mr = 295.68 | Dx = 1.520 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 9.923 (3) Å | µ = 0.31 mm−1 |
b = 9.527 (3) Å | T = 293 K |
c = 27.337 (7) Å | Prism, colourless |
V = 2584.5 (12) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 8 | |
Data collection top
Make? Model? CCD area-detector diffractometer | 2288 independent reflections |
Radiation source: fine-focus sealed tube | 1249 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1995) | h = −11→11 |
Tmin = 0.912, Tmax = 0.940 | k = −11→9 |
10028 measured reflections | l = −27→32 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.85111 (8) | 0.00988 (11) | 0.42905 (3) | 0.0568 (3) | |
O1 | 0.4469 (2) | 0.2117 (3) | 0.40453 (7) | 0.0559 (7) | |
O2 | 0.6346 (3) | 0.1315 (3) | 0.37250 (8) | 0.0632 (8) | |
O3 | 0.6486 (3) | 0.1049 (3) | 0.64008 (9) | 0.0675 (8) | |
O4 | 0.8201 (3) | −0.0147 (3) | 0.61549 (9) | 0.0617 (8) | |
N1 | 0.8181 (3) | 0.3445 (4) | 0.33471 (10) | 0.0656 (10) | |
H1A | 0.8544 | 0.4156 | 0.3489 | 0.079* | |
H1B | 0.7626 | 0.2920 | 0.3505 | 0.079* | |
N3 | 0.7211 (3) | 0.0585 (3) | 0.60780 (10) | 0.0482 (8) | |
C1 | 0.8479 (3) | 0.3153 (4) | 0.28809 (12) | 0.0449 (9) | |
C2 | 0.7873 (4) | 0.2023 (4) | 0.26399 (12) | 0.0549 (10) | |
H2A | 0.7289 | 0.1434 | 0.2809 | 0.066* | |
C3 | 0.8130 (4) | 0.1782 (4) | 0.21645 (13) | 0.0619 (11) | |
H3A | 0.7707 | 0.1035 | 0.2009 | 0.074* | |
N2 | 0.8976 (3) | 0.2589 (4) | 0.19116 (11) | 0.0593 (9) | |
H2B | 0.9126 | 0.2419 | 0.1607 | 0.071* | |
C4 | 0.9590 (4) | 0.3661 (5) | 0.21320 (13) | 0.0631 (12) | |
H4A | 1.0186 | 0.4211 | 0.1953 | 0.076* | |
C5 | 0.9373 (3) | 0.3973 (4) | 0.26093 (12) | 0.0577 (11) | |
H5A | 0.9816 | 0.4727 | 0.2754 | 0.069* | |
C6 | 0.5629 (3) | 0.1615 (3) | 0.40773 (11) | 0.0359 (8) | |
C7 | 0.6145 (3) | 0.1374 (3) | 0.45960 (11) | 0.0312 (7) | |
C8 | 0.7343 (3) | 0.0689 (3) | 0.47179 (11) | 0.0349 (8) | |
C9 | 0.7686 (3) | 0.0434 (4) | 0.52034 (11) | 0.0388 (9) | |
H9A | 0.8471 | −0.0050 | 0.5281 | 0.047* | |
C10 | 0.6850 (3) | 0.0907 (4) | 0.55653 (10) | 0.0370 (8) | |
C11 | 0.5685 (3) | 0.1631 (4) | 0.54680 (11) | 0.0418 (9) | |
H11A | 0.5141 | 0.1965 | 0.5719 | 0.050* | |
C12 | 0.5352 (3) | 0.1845 (3) | 0.49861 (11) | 0.0401 (9) | |
H12A | 0.4560 | 0.2326 | 0.4916 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0519 (6) | 0.0777 (8) | 0.0406 (5) | 0.0161 (5) | 0.0030 (4) | −0.0075 (5) |
O1 | 0.0558 (15) | 0.080 (2) | 0.0324 (14) | 0.0197 (15) | −0.0096 (12) | 0.0038 (12) |
O2 | 0.0723 (17) | 0.092 (2) | 0.0250 (13) | 0.0244 (16) | 0.0033 (12) | −0.0009 (13) |
O3 | 0.0739 (18) | 0.100 (2) | 0.0288 (14) | −0.0006 (17) | 0.0039 (13) | 0.0022 (14) |
O4 | 0.0658 (18) | 0.077 (2) | 0.0425 (15) | 0.0048 (16) | −0.0174 (13) | 0.0173 (14) |
N1 | 0.079 (2) | 0.086 (3) | 0.0318 (17) | −0.017 (2) | 0.0108 (16) | −0.0218 (16) |
N3 | 0.056 (2) | 0.059 (2) | 0.0298 (17) | −0.0160 (17) | −0.0084 (16) | 0.0083 (15) |
C1 | 0.044 (2) | 0.059 (3) | 0.032 (2) | 0.0078 (19) | 0.0025 (16) | −0.0078 (18) |
C2 | 0.073 (3) | 0.053 (3) | 0.039 (2) | −0.003 (2) | 0.0089 (19) | −0.0063 (18) |
C3 | 0.085 (3) | 0.061 (3) | 0.039 (2) | 0.013 (2) | 0.002 (2) | −0.011 (2) |
N2 | 0.063 (2) | 0.084 (3) | 0.0312 (17) | 0.026 (2) | 0.0051 (16) | −0.0070 (18) |
C4 | 0.049 (2) | 0.095 (4) | 0.045 (2) | 0.004 (2) | 0.0069 (19) | 0.007 (2) |
C5 | 0.053 (2) | 0.078 (3) | 0.042 (2) | −0.011 (2) | 0.0022 (19) | −0.007 (2) |
C6 | 0.044 (2) | 0.034 (2) | 0.0293 (19) | −0.0014 (17) | −0.0037 (16) | 0.0029 (15) |
C7 | 0.0383 (18) | 0.0278 (19) | 0.0275 (17) | −0.0039 (15) | −0.0020 (14) | 0.0011 (14) |
C8 | 0.0389 (18) | 0.036 (2) | 0.0293 (18) | −0.0034 (16) | −0.0023 (14) | −0.0017 (15) |
C9 | 0.0360 (18) | 0.044 (2) | 0.037 (2) | −0.0011 (16) | −0.0065 (16) | 0.0040 (16) |
C10 | 0.0460 (19) | 0.040 (2) | 0.0246 (17) | −0.0086 (17) | −0.0055 (15) | 0.0071 (15) |
C11 | 0.050 (2) | 0.048 (2) | 0.0279 (19) | −0.0005 (18) | 0.0044 (16) | −0.0003 (15) |
C12 | 0.048 (2) | 0.040 (2) | 0.0327 (19) | 0.0080 (17) | −0.0003 (16) | 0.0045 (16) |
Geometric parameters (Å, º) top
Cl1—C8 | 1.739 (3) | N2—H2B | 0.8600 |
O1—C6 | 1.250 (4) | C4—C5 | 1.356 (5) |
O2—C6 | 1.231 (4) | C4—H4A | 0.9300 |
O3—N3 | 1.221 (4) | C5—H5A | 0.9300 |
O4—N3 | 1.223 (3) | C6—O2 | 1.231 (4) |
N1—C1 | 1.338 (4) | C6—O1 | 1.250 (4) |
N1—H1A | 0.8600 | C6—C7 | 1.525 (4) |
N1—H1B | 0.8600 | C7—C8 | 1.396 (4) |
N3—C10 | 1.479 (4) | C7—C12 | 1.399 (4) |
C1—C5 | 1.396 (5) | C8—C9 | 1.392 (4) |
C1—C2 | 1.398 (5) | C9—C10 | 1.368 (4) |
C2—C3 | 1.344 (5) | C9—H9A | 0.9300 |
C2—H2A | 0.9300 | C10—C11 | 1.372 (4) |
C3—N2 | 1.331 (5) | C11—C12 | 1.374 (4) |
C3—H3A | 0.9300 | C11—H11A | 0.9300 |
N2—C4 | 1.333 (5) | C12—H12A | 0.9300 |
| | | |
C1—N1—H1A | 120.0 | O2—C6—O1 | 124.5 (3) |
C1—N1—H1B | 120.0 | O2—C6—O1 | 124.5 (3) |
H1A—N1—H1B | 120.0 | O2—C6—O1 | 124.5 (3) |
O3—N3—O4 | 123.8 (3) | O2—C6—C7 | 119.9 (3) |
O3—N3—C10 | 117.8 (3) | O2—C6—C7 | 119.9 (3) |
O4—N3—C10 | 118.4 (3) | O1—C6—C7 | 115.6 (3) |
N1—C1—C5 | 122.1 (3) | O1—C6—C7 | 115.6 (3) |
N1—C1—C2 | 120.9 (3) | C8—C7—C12 | 116.5 (3) |
C5—C1—C2 | 117.0 (3) | C8—C7—C6 | 125.3 (3) |
C3—C2—C1 | 120.3 (4) | C12—C7—C6 | 118.2 (3) |
C3—C2—H2A | 119.8 | C9—C8—C7 | 121.2 (3) |
C1—C2—H2A | 119.8 | C9—C8—Cl1 | 114.9 (2) |
N2—C3—C2 | 121.6 (4) | C7—C8—Cl1 | 123.9 (2) |
N2—C3—H3A | 119.2 | C10—C9—C8 | 118.9 (3) |
C2—C3—H3A | 119.2 | C10—C9—H9A | 120.5 |
C3—N2—C4 | 119.7 (3) | C8—C9—H9A | 120.5 |
C3—N2—H2B | 120.1 | C9—C10—C11 | 122.4 (3) |
C4—N2—H2B | 120.1 | C9—C10—N3 | 118.0 (3) |
N2—C4—C5 | 122.1 (4) | C11—C10—N3 | 119.5 (3) |
N2—C4—H4A | 119.0 | C10—C11—C12 | 117.6 (3) |
C5—C4—H4A | 119.0 | C10—C11—H11A | 121.2 |
C4—C5—C1 | 119.3 (4) | C12—C11—H11A | 121.2 |
C4—C5—H5A | 120.3 | C11—C12—C7 | 123.3 (3) |
C1—C5—H5A | 120.3 | C11—C12—H12A | 118.4 |
O2—C6—O1 | 124.5 (3) | C7—C12—H12A | 118.4 |
| | | |
N1—C1—C2—C3 | 176.7 (4) | O1—C6—C7—C12 | −5.8 (4) |
C5—C1—C2—C3 | −1.7 (5) | O1—C6—C7—C12 | −5.8 (4) |
C1—C2—C3—N2 | 1.0 (6) | C12—C7—C8—C9 | 3.0 (5) |
C2—C3—N2—C4 | 0.2 (6) | C6—C7—C8—C9 | −175.6 (3) |
C3—N2—C4—C5 | −0.6 (6) | C12—C7—C8—Cl1 | −176.8 (2) |
N2—C4—C5—C1 | −0.1 (6) | C6—C7—C8—Cl1 | 4.6 (5) |
N1—C1—C5—C4 | −177.2 (4) | C7—C8—C9—C10 | −2.1 (5) |
C2—C1—C5—C4 | 1.2 (5) | Cl1—C8—C9—C10 | 177.7 (3) |
O2—O2—C6—O1 | 0.0 (3) | C8—C9—C10—C11 | −0.3 (5) |
O2—O2—C6—O1 | 0.0 (3) | C8—C9—C10—N3 | 178.1 (3) |
O2—O2—C6—C7 | 0.0 (4) | O3—N3—C10—C9 | 177.6 (3) |
O1—O1—C6—O2 | 0.00 (13) | O4—N3—C10—C9 | −3.5 (5) |
O1—O1—C6—O2 | 0.00 (13) | O3—N3—C10—C11 | −4.0 (5) |
O1—O1—C6—C7 | 0.00 (13) | O4—N3—C10—C11 | 174.9 (3) |
O2—C6—C7—C8 | −7.1 (5) | C9—C10—C11—C12 | 1.7 (5) |
O2—C6—C7—C8 | −7.1 (5) | N3—C10—C11—C12 | −176.7 (3) |
O1—C6—C7—C8 | 172.7 (3) | C10—C11—C12—C7 | −0.6 (5) |
O1—C6—C7—C8 | 172.7 (3) | C8—C7—C12—C11 | −1.7 (5) |
O2—C6—C7—C12 | 174.3 (3) | C6—C7—C12—C11 | 177.0 (3) |
O2—C6—C7—C12 | 174.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O2 | 0.86 | 2.08 | 2.915 (4) | 165 |
N1—H1A···O2i | 0.86 | 2.16 | 2.961 (4) | 155 |
N2—H2B···O1ii | 0.86 | 1.84 | 2.699 (3) | 178 |
C3—H3A···O4iii | 0.93 | 2.64 | 3.434 (5) | 144 |
C12—H12A···O1 | 0.93 | 2.39 | 2.729 (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, z−1/2. |
(II) 4-Aminopyridium 2-chloro-5-nitrobenzoate
top
Crystal data top
C5H7N2+·C7H3ClNO4− | Z = 4 |
Mr = 295.68 | F(000) = 608 |
Monoclinic, P21/n | Dx = 1.535 Mg m−3 |
a = 12.624 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.270 (2) Å | µ = 0.32 mm−1 |
c = 14.023 (5) Å | T = 293 K |
β = 96.329 (5)° | Prism, colourless |
V = 1279.1 (7) Å3 | 0.35 × 0.30 × 0.25 mm |
Data collection top
Make? Model? CCD area-detector diffractometer | 2256 independent reflections |
Radiation source: fine-focus sealed tube | 1660 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1995) | h = −14→15 |
Tmin = 0.897, Tmax = 0.925 | k = −8→4 |
5062 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H 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 parameters | Δρmax = 0.15 e Å−3 |
3 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 1.01449 (4) | 0.13515 (8) | 0.11788 (4) | 0.04517 (18) | |
O1 | 0.83406 (12) | −0.1551 (2) | 0.05023 (10) | 0.0534 (4) | |
O2 | 0.69773 (11) | 0.0320 (2) | 0.06848 (10) | 0.0510 (4) | |
O3 | 0.67868 (12) | −0.0782 (2) | 0.43183 (10) | 0.0533 (4) | |
O4 | 0.82083 (13) | −0.0220 (3) | 0.52749 (10) | 0.0719 (6) | |
N1 | 0.54346 (17) | −0.1523 (3) | −0.39945 (13) | 0.0520 (5) | |
H2 | 0.5928 (17) | −0.134 (4) | −0.4396 (16) | 0.081 (9)* | |
H1 | 0.4803 (12) | −0.206 (3) | −0.4148 (17) | 0.073 (8)* | |
N2 | 0.63461 (15) | −0.0477 (3) | −0.11447 (12) | 0.0472 (5) | |
H3 | 0.656 (2) | −0.032 (4) | −0.0501 (8) | 0.080 (8)* | |
C1 | 0.57376 (16) | −0.1142 (3) | −0.30697 (14) | 0.0382 (5) | |
C2 | 0.50241 (16) | −0.1369 (3) | −0.23733 (14) | 0.0399 (5) | |
H2A | 0.4329 | −0.1754 | −0.2556 | 0.048* | |
N3 | 0.77181 (14) | −0.0301 (3) | 0.44713 (12) | 0.0454 (5) | |
C3 | 0.53540 (18) | −0.1024 (3) | −0.14320 (15) | 0.0444 (5) | |
H3A | 0.4876 | −0.1175 | −0.0979 | 0.053* | |
C4 | 0.70447 (18) | −0.0222 (3) | −0.17941 (16) | 0.0542 (6) | |
H4A | 0.7733 | 0.0167 | −0.1585 | 0.065* | |
C5 | 0.67689 (17) | −0.0517 (3) | −0.27428 (16) | 0.0499 (6) | |
H5A | 0.7261 | −0.0307 | −0.3178 | 0.060* | |
C6 | 0.78649 (16) | −0.0405 (3) | 0.09499 (13) | 0.0357 (5) | |
C7 | 0.83698 (14) | 0.0160 (3) | 0.19436 (13) | 0.0317 (4) | |
C8 | 0.78180 (15) | −0.0196 (3) | 0.27315 (13) | 0.0341 (5) | |
H8A | 0.7135 | −0.0689 | 0.2641 | 0.041* | |
C9 | 0.82873 (15) | 0.0184 (3) | 0.36465 (13) | 0.0358 (5) | |
C10 | 0.92851 (17) | 0.0979 (3) | 0.38164 (14) | 0.0417 (5) | |
H10A | 0.9578 | 0.1252 | 0.4438 | 0.050* | |
C11 | 0.98389 (16) | 0.1361 (3) | 0.30403 (14) | 0.0396 (5) | |
H11A | 1.0509 | 0.1907 | 0.3135 | 0.047* | |
C12 | 0.93874 (15) | 0.0925 (3) | 0.21184 (13) | 0.0340 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0388 (3) | 0.0564 (4) | 0.0414 (3) | −0.0021 (2) | 0.0093 (2) | 0.0090 (3) |
O1 | 0.0503 (9) | 0.0663 (11) | 0.0421 (8) | 0.0106 (8) | −0.0013 (7) | −0.0153 (8) |
O2 | 0.0401 (9) | 0.0727 (11) | 0.0374 (8) | 0.0110 (8) | −0.0084 (7) | −0.0068 (7) |
O3 | 0.0469 (10) | 0.0672 (11) | 0.0476 (9) | −0.0109 (8) | 0.0135 (8) | 0.0003 (8) |
O4 | 0.0607 (11) | 0.1253 (17) | 0.0285 (9) | −0.0042 (11) | −0.0002 (8) | 0.0081 (9) |
N1 | 0.0528 (13) | 0.0674 (14) | 0.0354 (10) | −0.0090 (11) | 0.0027 (9) | −0.0064 (9) |
N2 | 0.0458 (12) | 0.0585 (12) | 0.0349 (10) | 0.0080 (9) | −0.0056 (9) | −0.0021 (9) |
C1 | 0.0407 (12) | 0.0374 (11) | 0.0353 (11) | 0.0036 (9) | −0.0003 (9) | −0.0005 (9) |
C2 | 0.0350 (11) | 0.0421 (12) | 0.0417 (12) | −0.0053 (9) | −0.0003 (9) | −0.0022 (10) |
N3 | 0.0472 (12) | 0.0552 (12) | 0.0344 (10) | 0.0022 (9) | 0.0063 (9) | 0.0017 (8) |
C3 | 0.0455 (13) | 0.0485 (13) | 0.0393 (12) | 0.0012 (10) | 0.0057 (10) | 0.0010 (10) |
C4 | 0.0329 (12) | 0.0730 (17) | 0.0545 (15) | 0.0020 (12) | −0.0055 (11) | −0.0093 (12) |
C5 | 0.0375 (12) | 0.0682 (16) | 0.0448 (13) | −0.0004 (11) | 0.0080 (10) | −0.0043 (11) |
C6 | 0.0338 (11) | 0.0428 (12) | 0.0302 (10) | −0.0045 (10) | 0.0021 (9) | 0.0032 (9) |
C7 | 0.0322 (10) | 0.0331 (11) | 0.0291 (10) | 0.0043 (8) | −0.0001 (8) | 0.0020 (8) |
C8 | 0.0294 (10) | 0.0377 (11) | 0.0347 (10) | 0.0004 (9) | 0.0012 (8) | 0.0005 (9) |
C9 | 0.0365 (11) | 0.0410 (12) | 0.0300 (10) | 0.0013 (9) | 0.0035 (9) | 0.0013 (9) |
C10 | 0.0439 (12) | 0.0484 (13) | 0.0311 (10) | −0.0026 (10) | −0.0034 (9) | −0.0033 (9) |
C11 | 0.0333 (11) | 0.0413 (12) | 0.0424 (11) | −0.0070 (9) | −0.0031 (9) | 0.0009 (10) |
C12 | 0.0321 (11) | 0.0350 (11) | 0.0346 (10) | 0.0023 (8) | 0.0021 (9) | 0.0053 (9) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.7390 (19) | C3—H3A | 0.9300 |
O1—C6 | 1.237 (2) | C4—C5 | 1.355 (3) |
O2—C6 | 1.257 (2) | C4—H4A | 0.9300 |
O3—N3 | 1.223 (2) | C5—H5A | 0.9300 |
O4—N3 | 1.226 (2) | C6—O2 | 1.257 (2) |
N1—C1 | 1.340 (3) | C6—C7 | 1.524 (3) |
N1—H2 | 0.894 (10) | C7—C8 | 1.394 (3) |
N1—H1 | 0.892 (10) | C7—C12 | 1.397 (3) |
N2—C3 | 1.334 (3) | C8—C9 | 1.381 (3) |
N2—C4 | 1.349 (3) | C8—H8A | 0.9300 |
N2—H3 | 0.920 (10) | C9—C10 | 1.383 (3) |
C1—C5 | 1.407 (3) | C10—C11 | 1.385 (3) |
C1—C2 | 1.409 (3) | C10—H10A | 0.9300 |
C2—C3 | 1.363 (3) | C11—C12 | 1.391 (3) |
C2—H2A | 0.9300 | C11—H11A | 0.9300 |
N3—C9 | 1.470 (3) | | |
| | | |
C1—N1—H2 | 115.8 (18) | O1—C6—O2 | 126.80 (18) |
C1—N1—H1 | 118.4 (16) | O1—C6—O2 | 126.80 (18) |
H2—N1—H1 | 125 (3) | O1—C6—C7 | 117.91 (17) |
C3—N2—C4 | 119.96 (18) | O2—C6—C7 | 115.26 (17) |
C3—N2—H3 | 120.0 (16) | O2—C6—C7 | 115.26 (17) |
C4—N2—H3 | 120.0 (16) | C8—C7—C12 | 117.74 (17) |
N1—C1—C5 | 122.49 (19) | C8—C7—C6 | 118.66 (17) |
N1—C1—C2 | 120.69 (19) | C12—C7—C6 | 123.49 (16) |
C5—C1—C2 | 116.82 (18) | C9—C8—C7 | 119.91 (17) |
C3—C2—C1 | 119.94 (19) | C9—C8—H8A | 120.0 |
C3—C2—H2A | 120.0 | C7—C8—H8A | 120.0 |
C1—C2—H2A | 120.0 | C8—C9—C10 | 122.23 (17) |
O3—N3—O4 | 123.58 (17) | C8—C9—N3 | 119.10 (17) |
O3—N3—C9 | 118.33 (17) | C10—C9—N3 | 118.66 (17) |
O4—N3—C9 | 118.09 (18) | C9—C10—C11 | 118.54 (18) |
N2—C3—C2 | 121.60 (19) | C9—C10—H10A | 120.7 |
N2—C3—H3A | 119.2 | C11—C10—H10A | 120.7 |
C2—C3—H3A | 119.2 | C10—C11—C12 | 119.60 (18) |
N2—C4—C5 | 121.7 (2) | C10—C11—H11A | 120.2 |
N2—C4—H4A | 119.2 | C12—C11—H11A | 120.2 |
C5—C4—H4A | 119.2 | C11—C12—C7 | 121.92 (17) |
C4—C5—C1 | 120.0 (2) | C11—C12—Cl1 | 117.41 (15) |
C4—C5—H5A | 120.0 | C7—C12—Cl1 | 120.67 (14) |
C1—C5—H5A | 120.0 | | |
| | | |
N1—C1—C2—C3 | 178.2 (2) | C6—C7—C8—C9 | 175.51 (18) |
C5—C1—C2—C3 | −1.4 (3) | C7—C8—C9—C10 | 2.4 (3) |
C4—N2—C3—C2 | 1.1 (3) | C7—C8—C9—N3 | −176.48 (17) |
C1—C2—C3—N2 | −0.2 (3) | O3—N3—C9—C8 | −10.2 (3) |
C3—N2—C4—C5 | −0.3 (4) | O4—N3—C9—C8 | 168.88 (19) |
N2—C4—C5—C1 | −1.3 (4) | O3—N3—C9—C10 | 170.81 (19) |
N1—C1—C5—C4 | −177.4 (2) | O4—N3—C9—C10 | −10.1 (3) |
C2—C1—C5—C4 | 2.1 (3) | C8—C9—C10—C11 | −1.7 (3) |
O2—O2—C6—O1 | 0.00 (5) | N3—C9—C10—C11 | 177.26 (18) |
O2—O2—C6—C7 | 0.00 (4) | C9—C10—C11—C12 | −0.6 (3) |
O1—C6—C7—C8 | −118.1 (2) | C10—C11—C12—C7 | 2.1 (3) |
O2—C6—C7—C8 | 59.8 (2) | C10—C11—C12—Cl1 | −177.41 (16) |
O2—C6—C7—C8 | 59.8 (2) | C8—C7—C12—C11 | −1.3 (3) |
O1—C6—C7—C12 | 58.1 (3) | C6—C7—C12—C11 | −177.55 (18) |
O2—C6—C7—C12 | −124.1 (2) | C8—C7—C12—Cl1 | 178.16 (14) |
O2—C6—C7—C12 | −124.1 (2) | C6—C7—C12—Cl1 | 2.0 (3) |
C12—C7—C8—C9 | −0.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.89 (1) | 2.12 (1) | 3.006 (3) | 177 (2) |
N1—H2···O3ii | 0.89 (1) | 2.24 (1) | 3.113 (2) | 165 (2) |
N2—H3···O2 | 0.92 (1) | 1.75 (1) | 2.665 (2) | 172 (2) |
C5—H5A···O4ii | 0.93 | 2.59 | 3.491 (3) | 163 |
C3—H3A···O2iii | 0.93 | 2.50 | 3.271 (3) | 141 |
C4—H4A···Cl1iv | 0.93 | 2.90 | 3.651 (2) | 139 |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x, y, z−1; (iii) −x+1, −y, −z; (iv) −x+2, −y, −z. |
(III) 4-Aminopyridium 5-chloro-2-nitrobenzoate
top
Crystal data top
C5H7N2+·C7H3ClNO4− | Z = 4 |
Mr = 295.68 | F(000) = 608 |
Monoclinic, P21/c | Dx = 1.533 Mg m−3 |
a = 12.219 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.488 (4) Å | µ = 0.32 mm−1 |
c = 13.368 (6) Å | T = 293 K |
β = 112.467 (9)° | Prism, colourless |
V = 1281.1 (10) Å3 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Make? Model? CCD area-detector diffractometer | 2255 independent reflections |
Radiation source: fine-focus sealed tube | 1174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1995) | h = −14→10 |
Tmin = 0.911, Tmax = 0.940 | k = −10→9 |
5126 measured reflections | l = −10→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H 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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 1.08960 (10) | 0.22145 (13) | −0.03102 (10) | 0.0649 (4) | |
N1 | 0.8009 (3) | 0.4187 (4) | 0.2138 (3) | 0.0475 (9) | |
N2 | 0.5951 (3) | −0.1550 (4) | −0.0908 (3) | 0.0472 (10) | |
H1 | 0.586 (3) | −0.075 (5) | −0.070 (3) | 0.048 (14)* | |
N3 | 0.6563 (3) | −0.5932 (4) | −0.1812 (3) | 0.0454 (9) | |
H3 | 0.674 (3) | −0.592 (5) | −0.244 (3) | 0.060 (13)* | |
H2 | 0.652 (4) | −0.663 (5) | −0.140 (3) | 0.062 (16)* | |
O1 | 0.6377 (2) | 0.1612 (3) | −0.0350 (2) | 0.0440 (7) | |
O2 | 0.7186 (3) | 0.0543 (3) | 0.1294 (2) | 0.0616 (8) | |
O3 | 0.6973 (3) | 0.3825 (3) | 0.1829 (2) | 0.0648 (9) | |
O4 | 0.8469 (3) | 0.5061 (4) | 0.2911 (3) | 0.0923 (12) | |
C1 | 0.7172 (4) | 0.1468 (4) | 0.0573 (3) | 0.0402 (9) | |
C2 | 0.8297 (3) | 0.2433 (4) | 0.0798 (3) | 0.0364 (9) | |
C3 | 0.8992 (3) | 0.2036 (4) | 0.0227 (3) | 0.0414 (9) | |
H3A | 0.8724 | 0.1274 | −0.0312 | 0.050* | |
C4 | 1.0068 (4) | 0.2740 (4) | 0.0440 (3) | 0.0461 (10) | |
C5 | 1.0500 (4) | 0.3880 (5) | 0.1227 (4) | 0.0539 (11) | |
H5A | 1.1234 | 0.4345 | 0.1373 | 0.065* | |
C6 | 0.9815 (4) | 0.4307 (5) | 0.1790 (3) | 0.0514 (11) | |
H6A | 1.0083 | 0.5075 | 0.2326 | 0.062* | |
C7 | 0.8735 (3) | 0.3606 (4) | 0.1567 (3) | 0.0382 (9) | |
C8 | 0.5864 (3) | −0.2796 (5) | −0.0325 (3) | 0.0472 (10) | |
H8A | 0.5680 | −0.2646 | 0.0282 | 0.057* | |
C9 | 0.6043 (3) | −0.4270 (4) | −0.0617 (3) | 0.0397 (9) | |
H9A | 0.5978 | −0.5132 | −0.0214 | 0.048* | |
C10 | 0.6326 (3) | −0.4493 (4) | −0.1526 (3) | 0.0345 (9) | |
C11 | 0.6376 (3) | −0.3156 (4) | −0.2124 (3) | 0.0433 (10) | |
H11A | 0.6531 | −0.3260 | −0.2751 | 0.052* | |
C12 | 0.6199 (3) | −0.1724 (5) | −0.1784 (3) | 0.0468 (11) | |
H12A | 0.6251 | −0.0836 | −0.2172 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0541 (7) | 0.0647 (7) | 0.0901 (9) | 0.0088 (6) | 0.0433 (6) | 0.0117 (6) |
N1 | 0.057 (3) | 0.0383 (19) | 0.046 (2) | 0.0003 (18) | 0.0178 (19) | −0.0063 (17) |
N2 | 0.039 (2) | 0.030 (2) | 0.069 (3) | −0.0003 (16) | 0.0174 (19) | −0.012 (2) |
N3 | 0.054 (2) | 0.034 (2) | 0.051 (2) | 0.0028 (17) | 0.0233 (19) | −0.0047 (19) |
O1 | 0.0434 (17) | 0.0328 (14) | 0.0554 (18) | −0.0061 (12) | 0.0184 (15) | −0.0042 (13) |
O2 | 0.084 (2) | 0.0533 (17) | 0.0575 (19) | −0.0168 (16) | 0.0379 (17) | 0.0018 (15) |
O3 | 0.058 (2) | 0.068 (2) | 0.078 (2) | −0.0112 (17) | 0.0366 (18) | −0.0237 (17) |
O4 | 0.081 (3) | 0.112 (3) | 0.079 (2) | −0.014 (2) | 0.025 (2) | −0.056 (2) |
C1 | 0.053 (3) | 0.026 (2) | 0.050 (3) | −0.0039 (18) | 0.030 (2) | −0.006 (2) |
C2 | 0.043 (2) | 0.0288 (19) | 0.037 (2) | −0.0012 (17) | 0.0145 (18) | 0.0031 (17) |
C3 | 0.046 (3) | 0.034 (2) | 0.045 (2) | −0.0013 (19) | 0.0184 (19) | 0.0026 (18) |
C4 | 0.039 (2) | 0.040 (2) | 0.058 (3) | 0.010 (2) | 0.018 (2) | 0.015 (2) |
C5 | 0.033 (2) | 0.046 (3) | 0.076 (3) | −0.004 (2) | 0.012 (2) | 0.006 (2) |
C6 | 0.046 (3) | 0.038 (2) | 0.061 (3) | −0.004 (2) | 0.009 (2) | −0.003 (2) |
C7 | 0.046 (3) | 0.031 (2) | 0.037 (2) | 0.0031 (18) | 0.0157 (19) | 0.0035 (18) |
C8 | 0.042 (2) | 0.052 (3) | 0.052 (3) | −0.005 (2) | 0.023 (2) | −0.011 (2) |
C9 | 0.044 (2) | 0.031 (2) | 0.050 (2) | −0.0037 (18) | 0.0248 (19) | −0.0017 (19) |
C10 | 0.027 (2) | 0.029 (2) | 0.044 (2) | −0.0022 (16) | 0.0097 (17) | −0.0004 (17) |
C11 | 0.045 (3) | 0.044 (2) | 0.043 (2) | 0.0082 (18) | 0.0199 (19) | 0.0077 (19) |
C12 | 0.044 (3) | 0.037 (2) | 0.061 (3) | 0.0053 (18) | 0.022 (2) | 0.012 (2) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.733 (4) | C3—C4 | 1.372 (5) |
N1—O3 | 1.211 (4) | C3—H3A | 0.9300 |
N1—O4 | 1.220 (4) | C4—C5 | 1.378 (5) |
N1—C7 | 1.460 (5) | C5—C6 | 1.372 (6) |
N2—C12 | 1.325 (5) | C5—H5A | 0.9300 |
N2—C8 | 1.342 (5) | C6—C7 | 1.372 (5) |
N2—H1 | 0.76 (4) | C6—H6A | 0.9300 |
N3—C10 | 1.344 (4) | C8—C9 | 1.353 (5) |
N3—H3 | 0.94 (4) | C8—H8A | 0.9300 |
N3—H2 | 0.82 (4) | C9—C10 | 1.397 (5) |
O1—C1 | 1.251 (4) | C9—H9A | 0.9300 |
O2—C1 | 1.238 (4) | C10—C11 | 1.404 (5) |
C1—O1 | 1.251 (4) | C11—C12 | 1.344 (5) |
C1—C2 | 1.528 (5) | C11—H11A | 0.9300 |
C2—C3 | 1.383 (5) | C12—H12A | 0.9300 |
C2—C7 | 1.383 (5) | | |
| | | |
O3—N1—O4 | 121.7 (4) | C6—C5—H5A | 121.0 |
O3—N1—C7 | 120.1 (3) | C4—C5—H5A | 121.0 |
O4—N1—C7 | 118.2 (4) | C7—C6—C5 | 120.2 (4) |
C12—N2—C8 | 121.4 (4) | C7—C6—H6A | 119.9 |
C12—N2—H1 | 122 (3) | C5—C6—H6A | 119.9 |
C8—N2—H1 | 116 (3) | C6—C7—C2 | 122.8 (4) |
C10—N3—H3 | 113 (2) | C6—C7—N1 | 117.8 (3) |
C10—N3—H2 | 113 (3) | C2—C7—N1 | 119.4 (4) |
H3—N3—H2 | 134 (4) | N2—C8—C9 | 120.2 (4) |
O2—C1—O1 | 127.2 (4) | N2—C8—H8A | 119.9 |
O2—C1—O1 | 127.2 (4) | C9—C8—H8A | 119.9 |
O2—C1—C2 | 116.3 (4) | C8—C9—C10 | 119.8 (4) |
O1—C1—C2 | 116.3 (3) | C8—C9—H9A | 120.1 |
O1—C1—C2 | 116.3 (3) | C10—C9—H9A | 120.1 |
C3—C2—C7 | 116.2 (4) | N3—C10—C9 | 121.5 (4) |
C3—C2—C1 | 117.1 (3) | N3—C10—C11 | 120.7 (4) |
C7—C2—C1 | 126.6 (3) | C9—C10—C11 | 117.7 (3) |
C4—C3—C2 | 121.4 (4) | C12—C11—C10 | 119.4 (4) |
C4—C3—H3A | 119.3 | C12—C11—H11A | 120.3 |
C2—C3—H3A | 119.3 | C10—C11—H11A | 120.3 |
C3—C4—C5 | 121.5 (4) | N2—C12—C11 | 121.4 (4) |
C3—C4—Cl1 | 119.5 (3) | N2—C12—H12A | 119.3 |
C5—C4—Cl1 | 119.0 (3) | C11—C12—H12A | 119.3 |
C6—C5—C4 | 117.9 (4) | | |
| | | |
O1—O1—C1—O2 | 0.00 (9) | C3—C2—C7—C6 | −2.4 (5) |
O1—O1—C1—C2 | 0.00 (6) | C1—C2—C7—C6 | 173.3 (4) |
O2—C1—C2—C3 | 107.8 (4) | C3—C2—C7—N1 | 174.8 (3) |
O1—C1—C2—C3 | −66.8 (4) | C1—C2—C7—N1 | −9.5 (5) |
O1—C1—C2—C3 | −66.8 (4) | O3—N1—C7—C6 | 166.1 (3) |
O2—C1—C2—C7 | −67.8 (5) | O4—N1—C7—C6 | −12.4 (5) |
O1—C1—C2—C7 | 117.5 (4) | O3—N1—C7—C2 | −11.3 (5) |
O1—C1—C2—C7 | 117.5 (4) | O4—N1—C7—C2 | 170.2 (3) |
C7—C2—C3—C4 | 1.9 (5) | C12—N2—C8—C9 | 0.8 (6) |
C1—C2—C3—C4 | −174.3 (3) | N2—C8—C9—C10 | 0.3 (6) |
C2—C3—C4—C5 | −0.4 (6) | C8—C9—C10—N3 | 176.9 (3) |
C2—C3—C4—Cl1 | −179.3 (3) | C8—C9—C10—C11 | −2.0 (5) |
C3—C4—C5—C6 | −0.6 (6) | N3—C10—C11—C12 | −176.4 (4) |
Cl1—C4—C5—C6 | 178.2 (3) | C9—C10—C11—C12 | 2.5 (5) |
C4—C5—C6—C7 | 0.1 (6) | C8—N2—C12—C11 | −0.2 (6) |
C5—C6—C7—C2 | 1.5 (6) | C10—C11—C12—N2 | −1.5 (6) |
C5—C6—C7—N1 | −175.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H2···O1i | 0.82 (4) | 2.10 (4) | 2.925 (5) | 178 (4) |
N2—H1···O1 | 0.76 (4) | 2.10 (4) | 2.781 (5) | 150 (4) |
N3—H3···O2ii | 0.94 (4) | 2.00 (4) | 2.928 (5) | 171 (4) |
C3—H3A···O4iii | 0.93 | 2.54 | 3.414 (5) | 156 |
C12—H12A···O3iii | 0.93 | 2.52 | 3.424 (5) | 163 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y−1/2, z−1/2; (iii) x, −y+1/2, z−1/2. |
(IV) 4-Aminopyridium 4-chloro-2-nitrobenzoate
top
Crystal data top
C5H7N2+·C7H3ClNO4− | Z = 8 |
Mr = 295.68 | F(000) = 1216 |
Monoclinic, C2/c | Dx = 1.499 Mg m−3 |
a = 25.608 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.475 (6) Å | µ = 0.31 mm−1 |
c = 12.433 (10) Å | T = 293 K |
β = 103.749 (14)° | Prism, colourless |
V = 2621 (3) Å3 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Make? Model? CCD area-detector diffractometer | 2308 independent reflections |
Radiation source: fine-focus sealed tube | 1579 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1995) | h = −30→26 |
Tmin = 0.913, Tmax = 0.941 | k = −10→9 |
5262 measured reflections | l = −14→12 |
Refinement top
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) = 0.120 | w = 1/[σ2(Fo2) + (0.0586P)2 + 1.1026P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2308 reflections | Δρmax = 0.23 e Å−3 |
194 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.46273 (3) | 0.19463 (9) | 1.09806 (7) | 0.0691 (3) | |
O1 | 0.67956 (8) | 0.5915 (2) | 1.03009 (16) | 0.0627 (6) | |
O2 | 0.64006 (7) | 0.5301 (2) | 0.85667 (16) | 0.0623 (6) | |
O3 | 0.64154 (9) | 0.1909 (3) | 0.86890 (18) | 0.0766 (7) | |
O4 | 0.56335 (9) | 0.2125 (3) | 0.76201 (18) | 0.0929 (9) | |
N1 | 0.67789 (10) | 0.7470 (3) | 0.73599 (19) | 0.0543 (6) | |
H1 | 0.6714 (13) | 0.672 (4) | 0.785 (3) | 0.087 (11)* | |
N2 | 0.71828 (11) | 1.0873 (3) | 0.5373 (2) | 0.0553 (7) | |
H22 | 0.7050 (12) | 1.173 (3) | 0.530 (2) | 0.052 (9)* | |
H21 | 0.7497 (13) | 1.077 (3) | 0.510 (2) | 0.076 (10)* | |
N3 | 0.59496 (10) | 0.2314 (3) | 0.84955 (19) | 0.0499 (6) | |
C1 | 0.72010 (12) | 0.7263 (3) | 0.6911 (2) | 0.0545 (7) | |
H1A | 0.7399 | 0.6334 | 0.7052 | 0.065* | |
C2 | 0.73461 (10) | 0.8376 (3) | 0.6258 (2) | 0.0475 (7) | |
H2A | 0.7645 | 0.8213 | 0.5970 | 0.057* | |
C3 | 0.70500 (9) | 0.9766 (3) | 0.6015 (2) | 0.0405 (6) | |
C4 | 0.66046 (10) | 0.9934 (3) | 0.6484 (2) | 0.0500 (7) | |
H4A | 0.6391 | 1.0832 | 0.6341 | 0.060* | |
C5 | 0.64896 (11) | 0.8785 (4) | 0.7142 (2) | 0.0574 (8) | |
H5A | 0.6197 | 0.8918 | 0.7456 | 0.069* | |
C6 | 0.51680 (10) | 0.2849 (3) | 1.0603 (2) | 0.0440 (6) | |
C7 | 0.54252 (10) | 0.4093 (3) | 1.1214 (2) | 0.0472 (7) | |
H7A | 0.5318 | 0.4439 | 1.1838 | 0.057* | |
C8 | 0.58457 (10) | 0.4825 (3) | 1.0888 (2) | 0.0437 (6) | |
H8A | 0.6016 | 0.5677 | 1.1297 | 0.052* | |
C9 | 0.60195 (9) | 0.4326 (3) | 0.99716 (18) | 0.0361 (6) | |
C10 | 0.57535 (9) | 0.3041 (3) | 0.94051 (19) | 0.0377 (6) | |
C11 | 0.53250 (10) | 0.2298 (3) | 0.9689 (2) | 0.0435 (6) | |
H11A | 0.5149 | 0.1456 | 0.9276 | 0.052* | |
C12 | 0.64452 (10) | 0.5254 (3) | 0.9582 (2) | 0.0430 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0676 (5) | 0.0614 (5) | 0.0935 (7) | −0.0098 (4) | 0.0490 (4) | 0.0062 (4) |
O1 | 0.0603 (13) | 0.0647 (12) | 0.0681 (13) | −0.0248 (10) | 0.0255 (10) | −0.0151 (11) |
O2 | 0.0682 (13) | 0.0773 (13) | 0.0494 (12) | −0.0148 (11) | 0.0299 (9) | 0.0101 (10) |
O3 | 0.0678 (15) | 0.0954 (17) | 0.0710 (15) | 0.0281 (12) | 0.0255 (11) | −0.0145 (12) |
O4 | 0.0675 (15) | 0.162 (3) | 0.0502 (13) | −0.0161 (15) | 0.0163 (11) | −0.0370 (15) |
N1 | 0.0667 (16) | 0.0543 (14) | 0.0447 (14) | −0.0130 (13) | 0.0190 (12) | 0.0040 (12) |
N2 | 0.0563 (16) | 0.0445 (14) | 0.0714 (17) | 0.0042 (12) | 0.0278 (13) | 0.0142 (12) |
N3 | 0.0552 (15) | 0.0565 (14) | 0.0418 (13) | −0.0058 (12) | 0.0191 (11) | −0.0076 (11) |
C1 | 0.0603 (18) | 0.0512 (16) | 0.0517 (17) | 0.0056 (14) | 0.0125 (14) | 0.0093 (14) |
C2 | 0.0431 (14) | 0.0503 (15) | 0.0520 (16) | 0.0047 (12) | 0.0173 (12) | 0.0057 (13) |
C3 | 0.0396 (14) | 0.0402 (13) | 0.0424 (14) | −0.0045 (11) | 0.0114 (11) | −0.0023 (11) |
C4 | 0.0448 (15) | 0.0465 (15) | 0.0631 (18) | 0.0012 (12) | 0.0213 (13) | −0.0025 (13) |
C5 | 0.0530 (17) | 0.0678 (19) | 0.0595 (18) | −0.0126 (15) | 0.0298 (14) | −0.0105 (16) |
C6 | 0.0434 (15) | 0.0423 (14) | 0.0524 (16) | 0.0027 (11) | 0.0233 (12) | 0.0105 (12) |
C7 | 0.0568 (16) | 0.0485 (15) | 0.0445 (15) | 0.0041 (13) | 0.0284 (12) | 0.0013 (12) |
C8 | 0.0533 (16) | 0.0408 (14) | 0.0399 (14) | −0.0009 (12) | 0.0170 (11) | −0.0030 (11) |
C9 | 0.0371 (13) | 0.0379 (13) | 0.0354 (13) | 0.0026 (11) | 0.0126 (10) | 0.0046 (11) |
C10 | 0.0421 (14) | 0.0397 (13) | 0.0339 (13) | 0.0047 (11) | 0.0142 (10) | 0.0031 (11) |
C11 | 0.0435 (15) | 0.0392 (14) | 0.0489 (15) | −0.0020 (11) | 0.0129 (11) | 0.0013 (11) |
C12 | 0.0462 (15) | 0.0370 (13) | 0.0523 (16) | 0.0021 (12) | 0.0247 (13) | 0.0040 (13) |
Geometric parameters (Å, º) top
Cl1—C6 | 1.742 (3) | C2—H2A | 0.9300 |
O1—C12 | 1.240 (3) | C3—C4 | 1.406 (3) |
O2—C12 | 1.241 (3) | C4—C5 | 1.349 (4) |
O3—N3 | 1.209 (3) | C4—H4A | 0.9300 |
O4—N3 | 1.203 (3) | C5—H5A | 0.9300 |
N1—C5 | 1.330 (4) | C6—C7 | 1.372 (4) |
N1—C1 | 1.340 (4) | C6—C11 | 1.374 (3) |
N1—H1 | 0.93 (3) | C7—C8 | 1.384 (3) |
N2—C3 | 1.327 (3) | C7—H7A | 0.9300 |
N2—H22 | 0.80 (3) | C8—C9 | 1.385 (3) |
N2—H21 | 0.95 (3) | C8—H8A | 0.9300 |
N3—C10 | 1.477 (3) | C9—C10 | 1.384 (3) |
C1—C2 | 1.353 (4) | C9—C12 | 1.514 (3) |
C1—H1A | 0.9300 | C10—C11 | 1.382 (3) |
C2—C3 | 1.394 (4) | C11—H11A | 0.9300 |
| | | |
C5—N1—C1 | 119.4 (2) | C4—C5—H5A | 118.8 |
C5—N1—H1 | 122 (2) | C7—C6—C11 | 121.5 (2) |
C1—N1—H1 | 118 (2) | C7—C6—Cl1 | 119.7 (2) |
C3—N2—H22 | 123 (2) | C11—C6—Cl1 | 118.8 (2) |
C3—N2—H21 | 121.0 (18) | C6—C7—C8 | 119.2 (2) |
H22—N2—H21 | 115 (3) | C6—C7—H7A | 120.4 |
O4—N3—O3 | 124.2 (2) | C8—C7—H7A | 120.4 |
O4—N3—C10 | 118.1 (2) | C7—C8—C9 | 121.9 (2) |
O3—N3—C10 | 117.7 (2) | C7—C8—H8A | 119.1 |
N1—C1—C2 | 121.5 (3) | C9—C8—H8A | 119.1 |
N1—C1—H1A | 119.3 | C10—C9—C8 | 116.3 (2) |
C2—C1—H1A | 119.3 | C10—C9—C12 | 123.4 (2) |
C1—C2—C3 | 120.4 (2) | C8—C9—C12 | 120.1 (2) |
C1—C2—H2A | 119.8 | C11—C10—C9 | 123.6 (2) |
C3—C2—H2A | 119.8 | C11—C10—N3 | 116.1 (2) |
N2—C3—C2 | 121.6 (2) | C9—C10—N3 | 120.1 (2) |
N2—C3—C4 | 121.8 (3) | C6—C11—C10 | 117.5 (2) |
C2—C3—C4 | 116.6 (2) | C6—C11—H11A | 121.2 |
C5—C4—C3 | 119.6 (3) | C10—C11—H11A | 121.2 |
C5—C4—H4A | 120.2 | O1—C12—O2 | 126.5 (2) |
C3—C4—H4A | 120.2 | O1—C12—C9 | 117.2 (2) |
N1—C5—C4 | 122.5 (3) | O2—C12—C9 | 116.3 (2) |
N1—C5—H5A | 118.8 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.93 (3) | 1.79 (3) | 2.694 (3) | 164 (3) |
N2—H22···O1i | 0.80 (3) | 2.10 (3) | 2.891 (4) | 172 (3) |
N2—H21···O1ii | 0.95 (3) | 1.99 (3) | 2.931 (4) | 169 (3) |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) −x+3/2, y+1/2, −z+3/2. |