Preparation and single-crystal X-ray structure determination of three co-crystals of hydrogen squarate, HSQ
−, with 2-aminopyrimidine, 3-aminopyridine and 4-aminopyridine, and one of squarate, SQ
2-, with 8-aminoquinoline are reported. Their crystal packings are analyzed and discussed in terms of the intermolecular O—H
O, N—H
O/N and C—H
O hydrogen bonds formed. Although the fine details of the supramolecular architecture are barely rationalizable, the comparative analysis of the data makes it possible to suggest some simple rules that may be of general application for the packing of hydrogen-bonded crystals,
i.e. Rule 1: `All hydrogen-bond acceptors available in a molecule will be engaged in hydrogen bonding as far as there are available donors';
Rule 2: `The hydrogen-bond acceptors will be saturated in order of decreasing strength of the hydrogen bonds formed'.
Supporting information
CCDC references: 170354; 170355; 170356; 170357
For all compounds, data collection: CAD4 (Enraf-Nonius, 1984). Cell refinement: CAD4 Enraf-Nonius, 1984 for (1); CAD4 (Enraf-Nonius, 1984 for (2); CAD4 (Enraf-Nonius, 1984) for (3), (4). For all compounds, data reduction: MolEN (Fair, 1990; Enraf-Nonius, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII (Johnson, 1976) for (1), (3), (4); ORTEP II (Johnson, 1976) for (2). Software used to prepare material for publication: PARST (Nardelli, 1983, 1995), SHELXL97 (Sheldrick, 1997) for (1), (2); PARST (Nardelli, 1983, 1995); SHELXL97 (Sheldrick, 1997) for (3), (4).
(1) 2-aminopyridinium hydrogen squarate, 1:1
top
Crystal data top
C4H6N3·C4HO4 | Z = 2 |
Mr = 209.17 | F(000) = 216 |
Triclinic, P1 | Dx = 1.610 Mg m−3 |
a = 8.279 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.184 (1) Å | Cell parameters from 25 reflections |
c = 5.353 (2) Å | θ = 8–14° |
α = 99.72 (2)° | µ = 0.13 mm−1 |
β = 104.05 (2)° | T = 296 K |
γ = 87.73 (1)° | Plate, colourless |
V = 431.5 (2) Å3 | 0.52 × 0.36 × 0.10 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.013 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.0° |
Graphite monochromator | h = 0→10 |
ω/2θ scans | k = −13→13 |
2769 measured reflections | l = −7→6 |
2078 independent reflections | 3 standard reflections every 120 min |
1596 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.050 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.150 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1114P)2] where P = (Fo2 + 2Fc2)/3 |
2078 reflections | (Δ/σ)max = 0.003 |
164 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Crystal data top
C4H6N3·C4HO4 | γ = 87.73 (1)° |
Mr = 209.17 | V = 431.5 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.279 (1) Å | Mo Kα radiation |
b = 10.184 (1) Å | µ = 0.13 mm−1 |
c = 5.353 (2) Å | T = 296 K |
α = 99.72 (2)° | 0.52 × 0.36 × 0.10 mm |
β = 104.05 (2)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.013 |
2769 measured reflections | 3 standard reflections every 120 min |
2078 independent reflections | intensity decay: none |
1596 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.150 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.34 e Å−3 |
2078 reflections | Δρmin = −0.33 e Å−3 |
164 parameters | |
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 | |
O1 | 0.29393 (18) | 0.12644 (14) | −0.1800 (3) | 0.0487 (4) | |
O2 | 0.58959 (16) | 0.09413 (12) | 0.3332 (2) | 0.0415 (4) | |
O3 | 0.47929 (16) | 0.36437 (12) | 0.6376 (2) | 0.0409 (3) | |
O4 | 0.18791 (17) | 0.40146 (13) | 0.1066 (3) | 0.0469 (4) | |
C1 | 0.3493 (2) | 0.19378 (16) | 0.0535 (3) | 0.0315 (4) | |
C2 | 0.4760 (2) | 0.17740 (15) | 0.2742 (3) | 0.0301 (4) | |
C3 | 0.4280 (2) | 0.30333 (15) | 0.4165 (3) | 0.0299 (4) | |
C4 | 0.2944 (2) | 0.31983 (16) | 0.1741 (3) | 0.0314 (4) | |
N1 | 0.74921 (18) | 0.29039 (13) | 1.0142 (3) | 0.0325 (3) | |
N2 | 0.96332 (17) | 0.15882 (14) | 1.2202 (3) | 0.0313 (3) | |
N3 | 0.8191 (2) | 0.08904 (16) | 0.7977 (3) | 0.0407 (4) | |
C5 | 0.8434 (2) | 0.17901 (16) | 1.0099 (3) | 0.0294 (4) | |
C6 | 0.7655 (2) | 0.38114 (16) | 1.2329 (4) | 0.0359 (4) | |
C7 | 0.8801 (2) | 0.36211 (17) | 1.4511 (3) | 0.0377 (4) | |
C8 | 0.9793 (2) | 0.24902 (18) | 1.4319 (3) | 0.0360 (4) | |
H1 | 0.354 (3) | 0.047 (2) | −0.209 (5) | 0.060 (7)* | |
H6 | 0.688 (3) | 0.459 (2) | 1.212 (4) | 0.042 (5)* | |
H7 | 0.888 (3) | 0.425 (3) | 1.600 (5) | 0.057 (7)* | |
H8 | 1.073 (3) | 0.234 (2) | 1.592 (5) | 0.058 (7)* | |
H10 | 0.664 (3) | 0.302 (3) | 0.868 (5) | 0.057 (7)* | |
H31 | 0.889 (3) | 0.017 (2) | 0.798 (4) | 0.040 (5)* | |
H32 | 0.740 (3) | 0.092 (2) | 0.645 (5) | 0.053 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0570 (8) | 0.0386 (7) | 0.0306 (7) | 0.0181 (6) | −0.0149 (6) | −0.0085 (5) |
O2 | 0.0431 (7) | 0.0366 (6) | 0.0306 (6) | 0.0166 (5) | −0.0086 (5) | −0.0051 (5) |
O3 | 0.0471 (7) | 0.0386 (7) | 0.0269 (6) | 0.0113 (5) | −0.0008 (5) | −0.0060 (5) |
O4 | 0.0486 (8) | 0.0409 (7) | 0.0422 (7) | 0.0217 (6) | 0.0010 (6) | 0.0014 (6) |
C1 | 0.0322 (8) | 0.0294 (7) | 0.0264 (8) | 0.0049 (6) | −0.0013 (6) | 0.0001 (6) |
C2 | 0.0311 (8) | 0.0277 (7) | 0.0259 (7) | 0.0043 (6) | 0.0004 (6) | −0.0010 (6) |
C3 | 0.0305 (8) | 0.0290 (7) | 0.0270 (8) | 0.0051 (6) | 0.0035 (6) | 0.0021 (6) |
C4 | 0.0317 (8) | 0.0305 (8) | 0.0283 (8) | 0.0054 (6) | 0.0037 (6) | 0.0007 (6) |
N1 | 0.0345 (7) | 0.0309 (7) | 0.0287 (7) | 0.0086 (5) | 0.0028 (6) | 0.0049 (5) |
N2 | 0.0310 (7) | 0.0318 (7) | 0.0254 (7) | 0.0074 (5) | −0.0006 (5) | 0.0009 (5) |
N3 | 0.0478 (9) | 0.0374 (8) | 0.0255 (8) | 0.0143 (7) | −0.0050 (6) | −0.0030 (6) |
C5 | 0.0307 (8) | 0.0305 (8) | 0.0247 (8) | 0.0051 (6) | 0.0034 (6) | 0.0037 (6) |
C6 | 0.0421 (9) | 0.0241 (7) | 0.0426 (10) | 0.0071 (6) | 0.0155 (7) | 0.0022 (7) |
C7 | 0.0456 (10) | 0.0319 (8) | 0.0321 (9) | −0.0019 (7) | 0.0096 (7) | −0.0056 (7) |
C8 | 0.0367 (9) | 0.0379 (9) | 0.0278 (8) | −0.0006 (7) | 0.0015 (7) | −0.0008 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.304 (2) | N1—H10 | 0.94 (3) |
O1—H1 | 0.94 (3) | N2—C8 | 1.316 (2) |
O2—C2 | 1.2593 (19) | N2—C5 | 1.347 (2) |
O3—C3 | 1.223 (2) | N3—C5 | 1.312 (2) |
O4—C4 | 1.220 (2) | N3—H31 | 0.92 (2) |
C1—C2 | 1.405 (2) | N3—H32 | 0.92 (3) |
C1—C4 | 1.445 (2) | C6—C7 | 1.351 (3) |
C1—C3 | 2.038 (2) | C6—H6 | 1.00 (2) |
C2—C3 | 1.470 (2) | C7—C8 | 1.392 (2) |
C3—C4 | 1.516 (2) | C7—H7 | 0.93 (3) |
N1—C6 | 1.346 (2) | C8—H8 | 1.03 (3) |
N1—C5 | 1.351 (2) | | |
| | | |
C1—O1—H1 | 112.3 (16) | C6—N1—C5 | 121.16 (15) |
O1—C1—C2 | 135.96 (15) | C6—N1—H10 | 118.5 (16) |
O1—C1—C4 | 129.96 (15) | C5—N1—H10 | 120.1 (16) |
C2—C1—C4 | 94.08 (13) | C8—N2—C5 | 117.16 (15) |
O1—C1—C3 | 177.85 (14) | C5—N3—H31 | 117.7 (14) |
C2—C1—C3 | 46.14 (9) | C5—N3—H32 | 126.5 (15) |
C4—C1—C3 | 47.96 (9) | H31—N3—H32 | 116 (2) |
O2—C2—C1 | 136.68 (15) | N3—C5—N2 | 119.15 (15) |
O2—C2—C3 | 133.00 (15) | N3—C5—N1 | 119.85 (15) |
C1—C2—C3 | 90.29 (13) | N2—C5—N1 | 121.00 (15) |
O3—C3—C2 | 133.68 (15) | N1—C6—C7 | 119.61 (15) |
O3—C3—C4 | 137.69 (15) | N1—C6—H6 | 113.5 (13) |
C2—C3—C4 | 88.62 (13) | C7—C6—H6 | 126.9 (13) |
O3—C3—C1 | 177.19 (14) | C6—C7—C8 | 116.78 (16) |
C2—C3—C1 | 43.57 (9) | C6—C7—H7 | 118.1 (17) |
C4—C3—C1 | 45.06 (9) | C8—C7—H7 | 125.1 (17) |
O4—C4—C1 | 135.69 (16) | N2—C8—C7 | 124.15 (16) |
O4—C4—C3 | 137.32 (16) | N2—C8—H8 | 117.1 (14) |
C1—C4—C3 | 86.98 (13) | C7—C8—H8 | 118.7 (14) |
(2) 3-aminopyridinium. hydrogen squarate, 1:1
top
Crystal data top
C5H7N2·C4HO4 | Z = 4 |
Mr = 208.18 | F(000) = 432 |
Triclinic, P1 | Dx = 1.529 Mg m−3 |
a = 3.812 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.012 (2) Å | Cell parameters from 25 reflections |
c = 21.942 (5) Å | θ = 8–13° |
α = 100.78 (2)° | µ = 0.12 mm−1 |
β = 91.66 (2)° | T = 296 K |
γ = 88.26 (2)° | Prism, pale yellow |
V = 904.1 (4) Å3 | 0.52 × 0.30 × 0.14 mm |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.022 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.3° |
Graphite monochromator | h = 0→4 |
ω/2θ scans | k = −13→14 |
4454 measured reflections | l = −28→27 |
3913 independent reflections | 3 standard reflections every 120 min |
2471 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.064 | All H-atom parameters refined |
wR(F2) = 0.203 | w = 1/[σ2(Fo2) + (0.1236P)2 + 0.1121P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.018 |
3913 reflections | Δρmax = 0.35 e Å−3 |
336 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (4) |
Crystal data top
C5H7N2·C4HO4 | γ = 88.26 (2)° |
Mr = 208.18 | V = 904.1 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 3.812 (1) Å | Mo Kα radiation |
b = 11.012 (2) Å | µ = 0.12 mm−1 |
c = 21.942 (5) Å | T = 296 K |
α = 100.78 (2)° | 0.52 × 0.30 × 0.14 mm |
β = 91.66 (2)° | |
Data collection top
Enraf Nonius CAD-4 diffractometer | 2471 reflections with I > 2σ(I) |
4454 measured reflections | Rint = 0.022 |
3913 independent reflections | 3 standard reflections every 120 min |
Refinement top
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.203 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.35 e Å−3 |
3913 reflections | Δρmin = −0.39 e Å−3 |
336 parameters | |
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 | |
O11 | 0.9641 (6) | −0.32081 (18) | 0.46529 (10) | 0.0476 (6) | |
O21 | 0.7422 (6) | −0.61227 (18) | 0.44193 (11) | 0.0575 (7) | |
O31 | 0.3881 (6) | −0.57808 (18) | 0.31024 (11) | 0.0543 (6) | |
O41 | 0.6177 (6) | −0.29679 (18) | 0.33463 (11) | 0.0553 (6) | |
C11 | 0.8038 (7) | −0.3990 (2) | 0.42201 (13) | 0.0351 (6) | |
C21 | 0.7076 (7) | −0.5262 (2) | 0.41286 (13) | 0.0367 (6) | |
C31 | 0.5457 (7) | −0.5127 (2) | 0.35227 (14) | 0.0382 (6) | |
C41 | 0.6529 (7) | −0.3817 (2) | 0.36462 (13) | 0.0368 (6) | |
O12 | 0.2360 (6) | 0.17469 (19) | 0.04801 (11) | 0.0541 (6) | |
O22 | 0.1041 (6) | −0.11805 (19) | 0.05232 (10) | 0.0534 (6) | |
O32 | 0.5210 (7) | −0.0820 (2) | 0.18315 (12) | 0.0611 (7) | |
O42 | 0.6696 (6) | 0.19999 (18) | 0.17526 (10) | 0.0507 (6) | |
C12 | 0.3190 (7) | 0.0966 (2) | 0.08453 (14) | 0.0384 (6) | |
C22 | 0.2544 (7) | −0.0304 (2) | 0.08548 (13) | 0.0382 (6) | |
C32 | 0.4479 (8) | −0.0163 (3) | 0.14662 (14) | 0.0413 (7) | |
C42 | 0.5112 (7) | 0.1145 (2) | 0.14204 (13) | 0.0375 (6) | |
N11 | 0.9736 (6) | −0.0861 (2) | 0.35766 (12) | 0.0419 (6) | |
N21 | 1.0772 (9) | 0.1804 (3) | 0.28838 (15) | 0.0601 (8) | |
C51 | 1.0937 (7) | 0.1051 (2) | 0.33010 (13) | 0.0371 (6) | |
C61 | 1.2555 (7) | 0.1391 (2) | 0.38888 (14) | 0.0393 (7) | |
C71 | 1.2679 (8) | 0.0612 (3) | 0.42942 (16) | 0.0438 (7) | |
C81 | 1.1236 (8) | −0.0549 (3) | 0.41363 (15) | 0.0441 (7) | |
C91 | 0.9527 (7) | −0.0128 (2) | 0.31628 (15) | 0.0398 (7) | |
N12 | 0.8139 (6) | 0.4170 (2) | 0.14554 (13) | 0.0458 (6) | |
N22 | 1.1995 (8) | 0.7046 (3) | 0.21959 (15) | 0.0514 (7) | |
C52 | 1.0446 (7) | 0.6174 (2) | 0.17682 (15) | 0.0391 (6) | |
C62 | 0.9430 (8) | 0.6396 (3) | 0.11834 (14) | 0.0419 (7) | |
C72 | 0.7863 (9) | 0.5495 (3) | 0.07486 (17) | 0.0497 (8) | |
C82 | 0.7226 (8) | 0.4366 (3) | 0.09026 (17) | 0.0499 (8) | |
C92 | 0.9681 (8) | 0.5017 (3) | 0.19009 (15) | 0.0406 (7) | |
H11 | 1.057 (8) | −0.357 (3) | 0.4961 (16) | 0.048 (9)* | |
H12 | 0.101 (11) | 0.140 (4) | 0.003 (2) | 0.093 (15)* | |
H110 | 0.852 (11) | −0.177 (4) | 0.342 (2) | 0.099 (15)* | |
H211 | 0.945 (8) | 0.163 (3) | 0.2515 (17) | 0.045 (9)* | |
H212 | 1.165 (12) | 0.258 (4) | 0.299 (2) | 0.090 (14)* | |
H61 | 1.354 (9) | 0.220 (3) | 0.4030 (17) | 0.061 (10)* | |
H71 | 1.371 (7) | 0.075 (3) | 0.4623 (14) | 0.028 (7)* | |
H81 | 1.125 (8) | −0.113 (3) | 0.4450 (16) | 0.052 (9)* | |
H91 | 0.840 (8) | −0.044 (3) | 0.2774 (16) | 0.045 (8)* | |
H120 | 0.756 (14) | 0.329 (6) | 0.163 (3) | 0.14 (2)* | |
H221 | 1.310 (9) | 0.680 (3) | 0.2451 (17) | 0.043 (10)* | |
H222 | 1.283 (12) | 0.771 (5) | 0.209 (2) | 0.088 (14)* | |
H62 | 0.974 (8) | 0.720 (3) | 0.1107 (16) | 0.049 (9)* | |
H72 | 0.713 (9) | 0.567 (3) | 0.0386 (19) | 0.060 (11)* | |
H82 | 0.613 (11) | 0.375 (4) | 0.054 (2) | 0.084 (13)* | |
H92 | 1.043 (8) | 0.473 (3) | 0.2236 (15) | 0.038 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0696 (14) | 0.0269 (10) | 0.0463 (12) | −0.0210 (9) | −0.0208 (10) | 0.0072 (9) |
O21 | 0.0867 (16) | 0.0302 (10) | 0.0587 (14) | −0.0255 (10) | −0.0312 (12) | 0.0173 (10) |
O31 | 0.0739 (15) | 0.0323 (11) | 0.0564 (14) | −0.0238 (10) | −0.0241 (11) | 0.0073 (10) |
O41 | 0.0782 (15) | 0.0304 (10) | 0.0617 (14) | −0.0285 (10) | −0.0276 (11) | 0.0200 (10) |
C11 | 0.0410 (14) | 0.0219 (12) | 0.0422 (15) | −0.0123 (10) | −0.0024 (11) | 0.0035 (10) |
C21 | 0.0448 (15) | 0.0229 (12) | 0.0429 (15) | −0.0135 (10) | −0.0098 (12) | 0.0073 (11) |
C31 | 0.0442 (15) | 0.0213 (12) | 0.0490 (16) | −0.0128 (11) | −0.0049 (12) | 0.0052 (11) |
C41 | 0.0397 (14) | 0.0248 (12) | 0.0459 (16) | −0.0134 (10) | −0.0046 (12) | 0.0054 (11) |
O12 | 0.0777 (16) | 0.0357 (11) | 0.0514 (13) | −0.0196 (10) | −0.0222 (11) | 0.0154 (10) |
O22 | 0.0734 (15) | 0.0362 (11) | 0.0511 (13) | −0.0234 (10) | −0.0218 (11) | 0.0093 (10) |
O32 | 0.0820 (16) | 0.0399 (12) | 0.0663 (15) | −0.0250 (11) | −0.0279 (13) | 0.0230 (11) |
O42 | 0.0688 (14) | 0.0337 (11) | 0.0514 (13) | −0.0236 (10) | −0.0152 (10) | 0.0113 (9) |
C12 | 0.0438 (15) | 0.0283 (13) | 0.0441 (16) | −0.0099 (11) | −0.0025 (12) | 0.0083 (11) |
C22 | 0.0465 (15) | 0.0300 (13) | 0.0394 (15) | −0.0129 (11) | −0.0065 (12) | 0.0088 (11) |
C32 | 0.0490 (16) | 0.0298 (13) | 0.0467 (17) | −0.0141 (11) | −0.0076 (13) | 0.0107 (12) |
C42 | 0.0455 (15) | 0.0309 (13) | 0.0367 (14) | −0.0122 (11) | −0.0035 (12) | 0.0069 (11) |
N11 | 0.0463 (13) | 0.0250 (11) | 0.0538 (15) | −0.0143 (9) | −0.0033 (11) | 0.0042 (10) |
N21 | 0.084 (2) | 0.0406 (15) | 0.0599 (19) | −0.0315 (14) | −0.0205 (16) | 0.0182 (14) |
C51 | 0.0380 (14) | 0.0283 (13) | 0.0448 (15) | −0.0135 (10) | −0.0039 (11) | 0.0045 (11) |
C61 | 0.0381 (14) | 0.0251 (13) | 0.0517 (17) | −0.0117 (10) | −0.0063 (12) | −0.0010 (12) |
C71 | 0.0467 (16) | 0.0350 (15) | 0.0470 (18) | −0.0117 (12) | −0.0129 (14) | 0.0013 (13) |
C81 | 0.0501 (17) | 0.0342 (14) | 0.0503 (17) | −0.0124 (12) | −0.0029 (13) | 0.0123 (13) |
C91 | 0.0405 (15) | 0.0270 (13) | 0.0497 (17) | −0.0140 (11) | −0.0076 (12) | 0.0006 (12) |
N12 | 0.0472 (14) | 0.0297 (12) | 0.0616 (17) | −0.0119 (10) | −0.0048 (12) | 0.0103 (11) |
N22 | 0.0660 (18) | 0.0349 (14) | 0.0546 (17) | −0.0170 (12) | −0.0104 (15) | 0.0114 (13) |
C52 | 0.0357 (14) | 0.0280 (13) | 0.0550 (17) | −0.0075 (10) | 0.0010 (12) | 0.0102 (12) |
C62 | 0.0498 (16) | 0.0329 (14) | 0.0465 (17) | −0.0089 (12) | −0.0022 (13) | 0.0154 (13) |
C72 | 0.0555 (19) | 0.0435 (17) | 0.053 (2) | −0.0103 (13) | −0.0119 (15) | 0.0160 (15) |
C82 | 0.0514 (18) | 0.0372 (15) | 0.061 (2) | −0.0140 (13) | −0.0116 (15) | 0.0084 (14) |
C92 | 0.0458 (16) | 0.0342 (14) | 0.0450 (17) | −0.0082 (11) | −0.0038 (13) | 0.0155 (13) |
Geometric parameters (Å, º) top
O11—C11 | 1.307 (3) | N21—H212 | 0.92 (5) |
O11—H11 | 0.91 (4) | C51—C91 | 1.398 (3) |
O21—C21 | 1.240 (3) | C51—C61 | 1.404 (4) |
O31—C31 | 1.215 (3) | C61—C71 | 1.345 (4) |
O41—C41 | 1.242 (3) | C61—H61 | 0.97 (4) |
C11—C41 | 1.412 (4) | C71—C81 | 1.386 (4) |
C11—C21 | 1.434 (3) | C71—H71 | 0.80 (3) |
C11—C31 | 2.037 (4) | C81—H81 | 1.02 (4) |
C21—C31 | 1.480 (4) | C91—H91 | 0.95 (4) |
C31—C41 | 1.485 (3) | N12—C82 | 1.307 (4) |
O12—C12 | 1.307 (3) | N12—C92 | 1.353 (4) |
O12—H12 | 1.11 (5) | N12—H120 | 1.13 (6) |
O22—C22 | 1.239 (3) | N22—C52 | 1.348 (4) |
O32—C32 | 1.198 (4) | N22—H221 | 0.77 (4) |
O42—C42 | 1.239 (3) | N22—H222 | 0.88 (5) |
C12—C42 | 1.425 (4) | C52—C62 | 1.392 (4) |
C12—C22 | 1.431 (4) | C52—C92 | 1.400 (4) |
C22—C32 | 1.497 (4) | C62—C72 | 1.378 (4) |
C32—C42 | 1.490 (4) | C62—H62 | 0.95 (3) |
N11—C91 | 1.322 (4) | C72—C82 | 1.379 (4) |
N11—C81 | 1.329 (4) | C72—H72 | 0.89 (4) |
N11—H110 | 1.10 (5) | C82—H82 | 1.03 (5) |
N21—C51 | 1.344 (4) | C92—H92 | 0.89 (3) |
N21—H211 | 0.93 (4) | | |
| | | |
C11—O11—H11 | 113 (2) | H211—N21—H212 | 116 (4) |
O11—C11—C41 | 130.0 (2) | N21—C51—C91 | 121.0 (3) |
O11—C11—C21 | 136.6 (3) | N21—C51—C61 | 122.4 (3) |
C41—C11—C21 | 93.4 (2) | C91—C51—C61 | 116.6 (3) |
O11—C11—C31 | 176.8 (2) | C71—C61—C51 | 120.8 (2) |
C41—C11—C31 | 46.81 (15) | C71—C61—H61 | 117 (2) |
C21—C11—C31 | 46.59 (16) | C51—C61—H61 | 122 (2) |
O21—C21—C11 | 136.7 (3) | C61—C71—C81 | 120.5 (3) |
O21—C21—C31 | 134.6 (2) | C61—C71—H71 | 124 (2) |
C11—C21—C31 | 88.7 (2) | C81—C71—H71 | 115 (2) |
O31—C31—C21 | 136.7 (2) | N11—C81—C71 | 118.0 (3) |
O31—C31—C41 | 134.7 (3) | N11—C81—H81 | 121.5 (19) |
C21—C31—C41 | 88.6 (2) | C71—C81—H81 | 120.5 (19) |
O31—C31—C11 | 178.4 (2) | N11—C91—C51 | 120.2 (3) |
C21—C31—C11 | 44.75 (14) | N11—C91—H91 | 117 (2) |
C41—C31—C11 | 43.89 (15) | C51—C91—H91 | 122 (2) |
O41—C41—C11 | 137.6 (2) | C82—N12—C92 | 124.1 (3) |
O41—C41—C31 | 133.1 (3) | C82—N12—H120 | 123 (3) |
C11—C41—C31 | 89.3 (2) | C92—N12—H120 | 112 (3) |
C12—O12—H12 | 119 (2) | C52—N22—H221 | 116 (3) |
O12—C12—C42 | 130.1 (2) | C52—N22—H222 | 121 (3) |
O12—C12—C22 | 136.3 (3) | H221—N22—H222 | 114 (4) |
C42—C12—C22 | 93.5 (2) | N22—C52—C62 | 121.7 (3) |
O22—C22—C12 | 137.9 (3) | N22—C52—C92 | 121.3 (3) |
O22—C22—C32 | 133.3 (3) | C62—C52—C92 | 117.0 (3) |
C12—C22—C32 | 88.8 (2) | C72—C62—C52 | 121.2 (3) |
O32—C32—C42 | 135.9 (3) | C72—C62—H62 | 122 (2) |
O32—C32—C22 | 135.7 (3) | C52—C62—H62 | 117 (2) |
C42—C32—C22 | 88.3 (2) | C62—C72—C82 | 119.2 (3) |
O42—C42—C12 | 136.8 (3) | C62—C72—H72 | 120 (3) |
O42—C42—C32 | 133.9 (3) | C82—C72—H72 | 121 (3) |
C12—C42—C32 | 89.3 (2) | N12—C82—C72 | 119.4 (3) |
C91—N11—C81 | 123.9 (2) | N12—C82—H82 | 128 (2) |
C91—N11—H110 | 114 (3) | C72—C82—H82 | 113 (2) |
C81—N11—H110 | 122 (3) | N12—C92—C52 | 119.1 (3) |
C51—N21—H211 | 123 (2) | N12—C92—H92 | 115 (2) |
C51—N21—H212 | 120 (3) | C52—C92—H92 | 125 (2) |
(3) 4-aminopyridinium. hydrogen squarate, 1:1
top
Crystal data top
C5H7N2·C4HO4 | F(000) = 432 |
Mr = 208.17 | Dx = 1.519 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.283 (3) Å | Cell parameters from 25 reflections |
b = 7.068 (1) Å | θ = 9–13° |
c = 12.642 (2) Å | µ = 0.12 mm−1 |
β = 97.95 (2)° | T = 296 K |
V = 910.0 (3) Å3 | Irregular, colourless |
Z = 4 | 0.60 × 0.36 × 0.28 mm |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 30°, θmin = 2.0° |
Graphite monochromator | h = 0→14 |
ω/2θ scans | k = 0→9 |
2995 measured reflections | l = −17→17 |
2647 independent reflections | 3 standard reflections every 120 min |
2216 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0708P)2 + 0.1027P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.006 |
2647 reflections | Δρmax = 0.37 e Å−3 |
169 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.036 (5) |
Crystal data top
C5H7N2·C4HO4 | V = 910.0 (3) Å3 |
Mr = 208.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.283 (3) Å | µ = 0.12 mm−1 |
b = 7.068 (1) Å | T = 296 K |
c = 12.642 (2) Å | 0.60 × 0.36 × 0.28 mm |
β = 97.95 (2)° | |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.030 |
2995 measured reflections | 3 standard reflections every 120 min |
2647 independent reflections | intensity decay: none |
2216 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.119 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.37 e Å−3 |
2647 reflections | Δρmin = −0.18 e Å−3 |
169 parameters | |
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 | |
O1 | 0.59845 (7) | −0.05577 (15) | 0.66338 (6) | 0.0457 (2) | |
O2 | 0.32737 (7) | 0.08695 (14) | 0.51635 (6) | 0.0411 (2) | |
O3 | 0.17947 (8) | 0.08436 (15) | 0.72209 (7) | 0.0487 (2) | |
O4 | 0.45477 (7) | −0.04539 (15) | 0.86903 (6) | 0.0470 (2) | |
C1 | 0.47841 (9) | −0.01276 (15) | 0.67796 (7) | 0.0317 (2) | |
C2 | 0.36216 (9) | 0.04806 (14) | 0.61246 (7) | 0.0305 (2) | |
C3 | 0.29231 (9) | 0.04972 (15) | 0.70747 (8) | 0.0331 (2) | |
C4 | 0.41782 (9) | −0.01104 (16) | 0.77413 (8) | 0.0330 (2) | |
N1 | 0.26876 (9) | −0.10913 (16) | 1.00550 (9) | 0.0448 (2) | |
N2 | −0.08527 (9) | −0.25390 (15) | 1.09656 (9) | 0.0414 (2) | |
C5 | 0.03098 (9) | −0.20861 (14) | 1.06762 (8) | 0.0309 (2) | |
C6 | 0.12367 (10) | −0.09898 (16) | 1.13391 (9) | 0.0377 (2) | |
C7 | 0.23972 (11) | −0.05149 (18) | 1.10030 (11) | 0.0434 (3) | |
C8 | 0.18319 (12) | −0.21439 (18) | 0.94043 (10) | 0.0436 (3) | |
C9 | 0.06520 (10) | −0.26650 (16) | 0.96836 (9) | 0.0369 (2) | |
H1 | 0.6106 (17) | −0.065 (3) | 0.5917 (16) | 0.069 (5)* | |
H6 | 0.1019 (15) | −0.057 (2) | 1.1991 (14) | 0.054 (4)* | |
H7 | 0.3085 (16) | 0.020 (3) | 1.1445 (14) | 0.062 (5)* | |
H8 | 0.2160 (16) | −0.250 (2) | 0.8718 (13) | 0.059 (4)* | |
H9 | 0.0049 (14) | −0.338 (2) | 0.9199 (13) | 0.051 (4)* | |
H10 | 0.3468 (19) | −0.067 (3) | 0.9859 (17) | 0.078 (6)* | |
H21 | −0.1436 (16) | −0.310 (3) | 1.0539 (14) | 0.057 (4)* | |
H22 | −0.1125 (16) | −0.204 (3) | 1.1571 (15) | 0.062 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0282 (4) | 0.0817 (7) | 0.0279 (4) | 0.0133 (4) | 0.0059 (3) | 0.0032 (4) |
O2 | 0.0313 (4) | 0.0661 (5) | 0.0259 (3) | 0.0103 (3) | 0.0046 (3) | 0.0008 (3) |
O3 | 0.0286 (4) | 0.0805 (7) | 0.0386 (4) | 0.0083 (4) | 0.0099 (3) | −0.0029 (4) |
O4 | 0.0349 (4) | 0.0798 (7) | 0.0270 (4) | 0.0030 (4) | 0.0068 (3) | 0.0080 (4) |
C1 | 0.0269 (4) | 0.0428 (5) | 0.0260 (4) | 0.0016 (4) | 0.0053 (3) | −0.0003 (4) |
C2 | 0.0261 (4) | 0.0390 (5) | 0.0267 (4) | 0.0014 (3) | 0.0049 (3) | −0.0033 (3) |
C3 | 0.0279 (4) | 0.0437 (5) | 0.0283 (4) | 0.0007 (3) | 0.0059 (3) | −0.0027 (4) |
C4 | 0.0273 (4) | 0.0452 (5) | 0.0274 (4) | −0.0004 (4) | 0.0071 (3) | 0.0001 (4) |
N1 | 0.0301 (4) | 0.0497 (6) | 0.0563 (6) | 0.0016 (4) | 0.0122 (4) | 0.0107 (5) |
N2 | 0.0312 (4) | 0.0495 (5) | 0.0450 (5) | −0.0045 (4) | 0.0110 (4) | −0.0064 (4) |
C5 | 0.0273 (4) | 0.0328 (5) | 0.0327 (4) | 0.0024 (3) | 0.0044 (3) | 0.0014 (3) |
C6 | 0.0362 (5) | 0.0435 (5) | 0.0322 (5) | −0.0013 (4) | 0.0007 (4) | −0.0015 (4) |
C7 | 0.0315 (5) | 0.0454 (6) | 0.0501 (6) | −0.0036 (4) | −0.0055 (4) | 0.0050 (5) |
C8 | 0.0436 (6) | 0.0476 (6) | 0.0423 (6) | 0.0066 (5) | 0.0160 (4) | 0.0026 (5) |
C9 | 0.0363 (5) | 0.0399 (5) | 0.0349 (5) | 0.0018 (4) | 0.0062 (4) | −0.0043 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.3088 (12) | N2—C5 | 1.3365 (13) |
O1—H1 | 0.934 (19) | N2—H21 | 0.847 (18) |
O2—C2 | 1.2489 (12) | N2—H22 | 0.922 (18) |
O3—C3 | 1.2246 (12) | C5—C9 | 1.4100 (14) |
O4—C4 | 1.2315 (13) | C5—C6 | 1.4107 (15) |
C1—C2 | 1.4232 (13) | C6—C7 | 1.3629 (16) |
C1—C4 | 1.4407 (13) | C6—H6 | 0.932 (16) |
C2—C3 | 1.4823 (13) | C7—H7 | 0.980 (18) |
C3—C4 | 1.5032 (14) | C8—C9 | 1.3605 (15) |
N1—C7 | 1.3380 (18) | C8—H8 | 1.006 (15) |
N1—C8 | 1.3433 (18) | C9—H9 | 0.955 (16) |
N1—H10 | 0.92 (2) | | |
| | | |
C1—O1—H1 | 114.2 (11) | C5—N2—H22 | 121.4 (11) |
O1—C1—C2 | 136.12 (9) | H21—N2—H22 | 116.1 (15) |
O1—C1—C4 | 130.33 (9) | N2—C5—C9 | 121.12 (10) |
C2—C1—C4 | 93.55 (8) | N2—C5—C6 | 121.70 (10) |
O2—C2—C1 | 137.48 (9) | C9—C5—C6 | 117.18 (9) |
O2—C2—C3 | 132.91 (9) | C7—C6—C5 | 119.93 (10) |
C1—C2—C3 | 89.60 (8) | C7—C6—H6 | 121.7 (10) |
O3—C3—C2 | 134.37 (9) | C5—C6—H6 | 118.3 (10) |
O3—C3—C4 | 136.93 (9) | N1—C7—C6 | 121.18 (11) |
C2—C3—C4 | 88.70 (7) | N1—C7—H7 | 115.8 (10) |
O4—C4—C1 | 135.17 (9) | C6—C7—H7 | 122.9 (10) |
O4—C4—C3 | 136.70 (9) | N1—C8—C9 | 121.54 (11) |
C1—C4—C3 | 88.13 (8) | N1—C8—H8 | 113.4 (10) |
C7—N1—C8 | 120.58 (10) | C9—C8—H8 | 125.0 (10) |
C7—N1—H10 | 116.9 (13) | C8—C9—C5 | 119.59 (11) |
C8—N1—H10 | 122.4 (13) | C8—C9—H9 | 120.0 (9) |
C5—N2—H21 | 121.3 (11) | C5—C9—H9 | 120.3 (9) |
(4) 8-aminoquinolinium. squarate, 1:2
top
Crystal data top
C9H9N2·1/2(C4O4) | Z = 2 |
Mr = 201.20 | F(000) = 210 |
Triclinic, P1 | Dx = 1.470 Mg m−3 |
a = 7.209 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.861 (1) Å | Cell parameters from 25 reflections |
c = 8.443 (1) Å | θ = 7–13° |
α = 108.07 (1)° | µ = 0.10 mm−1 |
β = 91.62 (1)° | T = 296 K |
γ = 89.83 (1)° | Irregular, brown |
V = 454.7 (1) Å3 | 0.50 × 0.40 × 0.38 mm |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.010 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.5° |
Graphite monochromator | h = 0→10 |
ω/2θ scans | k = −10→11 |
2828 measured reflections | l = −11→11 |
2628 independent reflections | 3 standard reflections every 120 min |
2310 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.043 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.130 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0847P)2 + 0.0419P] where P = (Fo2 + 2Fc2)/3 |
2628 reflections | (Δ/σ)max = 0.012 |
172 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C9H9N2·1/2(C4O4) | γ = 89.83 (1)° |
Mr = 201.20 | V = 454.7 (1) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.209 (1) Å | Mo Kα radiation |
b = 7.861 (1) Å | µ = 0.10 mm−1 |
c = 8.443 (1) Å | T = 296 K |
α = 108.07 (1)° | 0.50 × 0.40 × 0.38 mm |
β = 91.62 (1)° | |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.010 |
2828 measured reflections | 3 standard reflections every 120 min |
2628 independent reflections | intensity decay: none |
2310 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.130 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.27 e Å−3 |
2628 reflections | Δρmin = −0.27 e Å−3 |
172 parameters | |
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 | |
O1 | 0.08530 (12) | 0.13517 (10) | 0.27261 (9) | 0.0459 (2) | |
O2 | 0.14521 (14) | 0.22187 (11) | −0.07223 (9) | 0.0543 (3) | |
C1 | 0.03815 (13) | 0.06131 (12) | 0.12260 (11) | 0.0330 (2) | |
C2 | 0.06570 (14) | 0.10087 (12) | −0.03361 (11) | 0.0351 (2) | |
N1 | 0.20734 (11) | 0.46712 (10) | 0.37370 (10) | 0.03399 (19) | |
N2 | 0.22334 (14) | 0.28202 (12) | 0.61632 (11) | 0.0416 (2) | |
C3 | 0.19405 (16) | 0.54981 (15) | 0.25855 (14) | 0.0430 (2) | |
C4 | 0.24484 (17) | 0.72885 (15) | 0.29561 (17) | 0.0490 (3) | |
C5 | 0.31132 (16) | 0.81790 (14) | 0.45129 (17) | 0.0465 (3) | |
C6 | 0.32990 (13) | 0.73177 (12) | 0.57548 (14) | 0.0385 (2) | |
C7 | 0.27198 (11) | 0.55021 (11) | 0.53302 (11) | 0.03162 (19) | |
C8 | 0.40100 (17) | 0.81913 (15) | 0.73718 (16) | 0.0503 (3) | |
C9 | 0.40883 (18) | 0.72878 (18) | 0.85146 (15) | 0.0544 (3) | |
C10 | 0.34735 (17) | 0.55103 (17) | 0.81138 (13) | 0.0465 (3) | |
C11 | 0.27786 (13) | 0.45678 (13) | 0.65370 (11) | 0.0345 (2) | |
H1 | 0.169 (2) | 0.343 (3) | 0.341 (2) | 0.064 (5)* | |
H21 | 0.1996 (19) | 0.252 (2) | 0.7069 (19) | 0.048 (4)* | |
H22 | 0.156 (2) | 0.233 (2) | 0.520 (2) | 0.062 (4)* | |
H3 | 0.148 (2) | 0.467 (2) | 0.146 (2) | 0.059 (4)* | |
H4 | 0.228 (3) | 0.787 (3) | 0.208 (2) | 0.073 (5)* | |
H5 | 0.336 (3) | 0.941 (3) | 0.481 (2) | 0.079 (5)* | |
H8 | 0.440 (3) | 0.953 (3) | 0.758 (3) | 0.088 (6)* | |
H9 | 0.463 (3) | 0.789 (3) | 0.969 (3) | 0.080 (6)* | |
H10 | 0.350 (3) | 0.488 (3) | 0.896 (2) | 0.070 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0716 (5) | 0.0379 (4) | 0.0281 (3) | −0.0196 (3) | −0.0111 (3) | 0.0108 (3) |
O2 | 0.0850 (6) | 0.0457 (4) | 0.0355 (4) | −0.0318 (4) | −0.0066 (4) | 0.0177 (3) |
C1 | 0.0425 (4) | 0.0297 (4) | 0.0277 (4) | −0.0070 (3) | −0.0040 (3) | 0.0107 (3) |
C2 | 0.0465 (5) | 0.0319 (4) | 0.0275 (4) | −0.0093 (3) | −0.0036 (3) | 0.0105 (3) |
N1 | 0.0383 (4) | 0.0297 (4) | 0.0340 (4) | −0.0046 (3) | −0.0005 (3) | 0.0100 (3) |
N2 | 0.0562 (5) | 0.0377 (4) | 0.0321 (4) | −0.0122 (3) | −0.0021 (3) | 0.0126 (3) |
C3 | 0.0502 (5) | 0.0397 (5) | 0.0424 (5) | −0.0053 (4) | −0.0046 (4) | 0.0180 (4) |
C4 | 0.0533 (6) | 0.0406 (5) | 0.0611 (7) | −0.0026 (4) | −0.0025 (5) | 0.0276 (5) |
C5 | 0.0456 (5) | 0.0292 (4) | 0.0661 (7) | −0.0028 (4) | 0.0028 (5) | 0.0164 (4) |
C6 | 0.0349 (4) | 0.0281 (4) | 0.0485 (5) | −0.0033 (3) | 0.0043 (4) | 0.0057 (4) |
C7 | 0.0300 (4) | 0.0282 (4) | 0.0341 (4) | −0.0025 (3) | 0.0022 (3) | 0.0059 (3) |
C8 | 0.0506 (6) | 0.0363 (5) | 0.0531 (6) | −0.0113 (4) | 0.0008 (5) | −0.0022 (4) |
C9 | 0.0572 (6) | 0.0533 (6) | 0.0405 (5) | −0.0141 (5) | −0.0040 (5) | −0.0030 (5) |
C10 | 0.0512 (6) | 0.0510 (6) | 0.0328 (5) | −0.0101 (4) | −0.0027 (4) | 0.0066 (4) |
C11 | 0.0352 (4) | 0.0348 (4) | 0.0319 (4) | −0.0038 (3) | 0.0023 (3) | 0.0078 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.2560 (11) | C4—C5 | 1.3576 (18) |
O2—C2 | 1.2433 (11) | C4—H4 | 0.986 (19) |
C1—C2i | 1.4595 (12) | C5—C6 | 1.4169 (16) |
C1—C2 | 1.4647 (12) | C5—H5 | 0.94 (2) |
C2—C1i | 1.4595 (12) | C6—C8 | 1.4068 (16) |
N1—C3 | 1.3280 (13) | C6—C7 | 1.4204 (12) |
N1—C7 | 1.3691 (12) | C7—C11 | 1.4286 (13) |
N1—H1 | 0.970 (19) | C8—C9 | 1.364 (2) |
N2—C11 | 1.3670 (12) | C8—H8 | 1.05 (2) |
N2—H21 | 0.888 (15) | C9—C10 | 1.4019 (17) |
N2—H22 | 0.913 (18) | C9—H9 | 1.02 (2) |
C3—C4 | 1.3914 (15) | C10—C11 | 1.3874 (14) |
C3—H3 | 1.016 (17) | C10—H10 | 0.990 (19) |
| | | |
O1—C1—C2i | 134.23 (8) | C6—C5—H5 | 118.5 (11) |
O1—C1—C2 | 135.00 (8) | C8—C6—C5 | 122.72 (10) |
C2i—C1—C2 | 90.77 (7) | C8—C6—C7 | 119.52 (10) |
O2—C2—C1i | 135.90 (9) | C5—C6—C7 | 117.76 (10) |
O2—C2—C1 | 134.86 (9) | N1—C7—C6 | 118.34 (9) |
C1i—C2—C1 | 89.23 (7) | N1—C7—C11 | 120.57 (8) |
C3—N1—C7 | 122.80 (9) | C6—C7—C11 | 121.09 (9) |
C3—N1—H1 | 117.3 (10) | C9—C8—C6 | 119.22 (10) |
C7—N1—H1 | 119.9 (10) | C9—C8—H8 | 126.3 (12) |
C11—N2—H21 | 112.3 (10) | C6—C8—H8 | 114.5 (12) |
C11—N2—H22 | 117.7 (11) | C8—C9—C10 | 121.46 (11) |
H21—N2—H22 | 120.6 (15) | C8—C9—H9 | 120.4 (11) |
N1—C3—C4 | 120.87 (10) | C10—C9—H9 | 118.1 (11) |
N1—C3—H3 | 112.4 (9) | C11—C10—C9 | 122.14 (11) |
C4—C3—H3 | 126.7 (9) | C11—C10—H10 | 117.0 (11) |
C5—C4—C3 | 118.98 (10) | C9—C10—H10 | 120.8 (11) |
C5—C4—H4 | 122.5 (11) | N2—C11—C10 | 121.07 (9) |
C3—C4—H4 | 118.5 (11) | N2—C11—C7 | 122.36 (8) |
C4—C5—C6 | 121.21 (9) | C10—C11—C7 | 116.54 (9) |
C4—C5—H5 | 120.0 (11) | | |
Symmetry code: (i) −x, −y, −z. |
Experimental details
| (1) | (2) | (3) | (4) |
Crystal data |
Chemical formula | C4H6N3·C4HO4 | C5H7N2·C4HO4 | C5H7N2·C4HO4 | C9H9N2·1/2(C4O4) |
Mr | 209.17 | 208.18 | 208.17 | 201.20 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 296 | 296 | 296 | 296 |
a, b, c (Å) | 8.279 (1), 10.184 (1), 5.353 (2) | 3.812 (1), 11.012 (2), 21.942 (5) | 10.283 (3), 7.068 (1), 12.642 (2) | 7.209 (1), 7.861 (1), 8.443 (1) |
α, β, γ (°) | 99.72 (2), 104.05 (2), 87.73 (1) | 100.78 (2), 91.66 (2), 88.26 (2) | 90, 97.95 (2), 90 | 108.07 (1), 91.62 (1), 89.83 (1) |
V (Å3) | 431.5 (2) | 904.1 (4) | 910.0 (3) | 454.7 (1) |
Z | 2 | 4 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.13 | 0.12 | 0.12 | 0.10 |
Crystal size (mm) | 0.52 × 0.36 × 0.10 | 0.52 × 0.30 × 0.14 | 0.60 × 0.36 × 0.28 | 0.50 × 0.40 × 0.38 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 | Enraf Nonius CAD-4 | Enraf Nonius CAD-4 | Enraf Nonius CAD-4 |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2769, 2078, 1596 | 4454, 3913, 2471 | 2995, 2647, 2216 | 2828, 2628, 2310 |
Rint | 0.013 | 0.022 | 0.030 | 0.010 |
(sin θ/λ)max (Å−1) | 0.661 | 0.639 | 0.703 | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.150, 1.02 | 0.064, 0.203, 1.06 | 0.038, 0.119, 1.07 | 0.043, 0.130, 1.06 |
No. of reflections | 2078 | 3913 | 2647 | 2628 |
No. of parameters | 164 | 336 | 169 | 172 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.34, −0.33 | 0.35, −0.39 | 0.37, −0.18 | 0.27, −0.27 |