Buy article online - an online subscription or single-article purchase is required to access this article.
Since 6-aminouracil derivatives show diversified use in various fields of application, we crystallized 6-aminouracil to examine its preferred hydrogen-bonding frameworks. 6-Aminouracil shows two rigid hydrogen-bonding sites,
viz. one acceptor-donor-acceptor (
ADA) site and one donor-donor-acceptor (
DDA) site. During various crystallization attempts, we obtained three structures, namely two dimethylacetamide monosolvates, C
4H
5N
3O
2·C
4H
9NO, and a 1-methylpyrrolidin-2-one monosolvate, C
4H
5N
3O
2·C
5H
9NO. In all three structures,
R21(6) N-H
O hydrogen-bonding patterns link the molecules to their respective solvent molecules. The formation of
R22(8) N-H
O hydrogen-bond motifs between 6-aminouracil molecules can only be found in two-dimensional frameworks, whereas
R33(14) N-H
O patterns are present when zigzag chzins of 6-aminouracil molecules are formed.
Supporting information
CCDC references: 967600; 967601; 967602
For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for (Ia), (Ib); SHELXL97 (Sheldrick, 2008 for (Ic). Molecular graphics: Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008) for (Ia); Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008) for (Ib), (Ic). For all compounds, software used to prepare material for publication: publCIF (Westrip, 2010).
(Ia) 6-Aminouracil dimethylacetamide monosolvate
top
Crystal data top
C4H5N3O2·C4H9NO | F(000) = 456 |
Mr = 214.23 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10028 reflections |
a = 7.5434 (6) Å | θ = 3.6–26.0° |
b = 13.0020 (14) Å | µ = 0.11 mm−1 |
c = 10.5130 (9) Å | T = 173 K |
β = 92.728 (7)° | Block, colourless |
V = 1029.94 (16) Å3 | 0.50 × 0.25 × 0.20 mm |
Z = 4 | |
Data collection top
Stoe IPDS II two-circle- diffractometer | 1934 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1573 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.199 |
ω scans | θmax = 25.7°, θmin = 3.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.948, Tmax = 0.979 | k = −15→15 |
18537 measured reflections | l = −12→12 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.089P)2 + 0.655P] where P = (Fo2 + 2Fc2)/3 |
1934 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 0.43 e Å−3 |
13 restraints | Δρmin = −0.36 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 | Occ. (<1) |
N1 | 0.3340 (3) | 0.46952 (14) | 0.3683 (2) | 0.0273 (5) | |
H1 | 0.294 (4) | 0.494 (2) | 0.439 (2) | 0.033* | |
C2 | 0.3373 (3) | 0.53561 (17) | 0.2676 (2) | 0.0267 (5) | |
O2 | 0.2784 (3) | 0.62310 (12) | 0.27295 (18) | 0.0357 (5) | |
N3 | 0.4094 (3) | 0.49673 (14) | 0.16167 (19) | 0.0275 (5) | |
H3 | 0.419 (4) | 0.5391 (18) | 0.098 (2) | 0.033* | |
C4 | 0.4785 (3) | 0.39847 (16) | 0.1506 (2) | 0.0253 (5) | |
O4 | 0.5416 (2) | 0.37412 (12) | 0.04642 (16) | 0.0316 (5) | |
C5 | 0.4726 (3) | 0.33477 (17) | 0.2577 (2) | 0.0261 (6) | |
H5 | 0.5161 | 0.2663 | 0.2546 | 0.031* | |
C6 | 0.4036 (3) | 0.37188 (16) | 0.3675 (2) | 0.0265 (5) | |
N6 | 0.3968 (3) | 0.32070 (16) | 0.4761 (2) | 0.0346 (6) | |
H61 | 0.350 (4) | 0.354 (3) | 0.545 (3) | 0.042* | |
H62 | 0.446 (4) | 0.261 (3) | 0.486 (3) | 0.042* | |
C1X | 0.1344 (4) | 0.4509 (3) | 0.8365 (3) | 0.0498 (8) | |
H1X1 | 0.0820 | 0.4969 | 0.8983 | 0.075* | 0.580 (10) |
H1X2 | 0.2515 | 0.4282 | 0.8697 | 0.075* | 0.580 (10) |
H1X3 | 0.0573 | 0.3910 | 0.8221 | 0.075* | 0.580 (10) |
H4XA | 0.0980 | 0.4520 | 0.9248 | 0.075* | 0.420 (10) |
H4XB | 0.2613 | 0.4351 | 0.8352 | 0.075* | 0.420 (10) |
H4XC | 0.0665 | 0.3983 | 0.7886 | 0.075* | 0.420 (10) |
O2X | 0.2133 (3) | 0.47928 (16) | 0.6096 (2) | 0.0482 (6) | |
C4X | 0.1023 (4) | 0.6645 (2) | 0.5923 (3) | 0.0430 (7) | |
H4X1 | 0.0511 | 0.7328 | 0.6051 | 0.064* | 0.580 (10) |
H4X2 | 0.0363 | 0.6296 | 0.5223 | 0.064* | 0.580 (10) |
H4X3 | 0.2269 | 0.6716 | 0.5714 | 0.064* | 0.580 (10) |
H1XA | 0.0507 | 0.7108 | 0.6541 | 0.064* | 0.420 (10) |
H1XB | 0.0174 | 0.6543 | 0.5199 | 0.064* | 0.420 (10) |
H1XC | 0.2116 | 0.6948 | 0.5623 | 0.064* | 0.420 (10) |
C5X | 0.0302 (4) | 0.6506 (3) | 0.8348 (3) | 0.0513 (8) | |
H5X1 | −0.0121 | 0.7207 | 0.8175 | 0.077* | 0.580 (10) |
H5X2 | 0.1299 | 0.6526 | 0.8980 | 0.077* | 0.580 (10) |
H5X3 | −0.0663 | 0.6094 | 0.8679 | 0.077* | 0.580 (10) |
H5XA | 0.0021 | 0.6357 | 0.9230 | 0.077* | 0.420 (10) |
H5XB | −0.0775 | 0.6734 | 0.7871 | 0.077* | 0.420 (10) |
H5XC | 0.1201 | 0.7050 | 0.8339 | 0.077* | 0.420 (10) |
C2X | 0.1531 (6) | 0.5070 (4) | 0.7135 (5) | 0.0321 (15) | 0.580 (10) |
N3X | 0.0907 (6) | 0.6024 (4) | 0.7121 (5) | 0.0346 (14) | 0.580 (10) |
C2X' | 0.1437 (8) | 0.5620 (4) | 0.6546 (6) | 0.0291 (19) | 0.420 (10) |
N3X' | 0.0993 (7) | 0.5568 (4) | 0.7751 (5) | 0.0318 (19) | 0.420 (10) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0346 (11) | 0.0191 (9) | 0.0286 (11) | 0.0017 (8) | 0.0048 (8) | −0.0003 (8) |
C2 | 0.0304 (12) | 0.0165 (11) | 0.0328 (13) | −0.0009 (9) | −0.0013 (10) | 0.0001 (9) |
O2 | 0.0469 (11) | 0.0184 (9) | 0.0423 (11) | 0.0052 (7) | 0.0061 (8) | 0.0012 (7) |
N3 | 0.0376 (11) | 0.0180 (10) | 0.0265 (11) | 0.0002 (8) | −0.0008 (9) | 0.0029 (8) |
C4 | 0.0305 (12) | 0.0169 (10) | 0.0283 (12) | −0.0024 (9) | −0.0011 (9) | −0.0024 (9) |
O4 | 0.0487 (11) | 0.0198 (8) | 0.0265 (9) | −0.0003 (7) | 0.0053 (8) | −0.0010 (6) |
C5 | 0.0347 (13) | 0.0162 (10) | 0.0274 (13) | 0.0002 (9) | 0.0003 (10) | 0.0009 (9) |
C6 | 0.0304 (12) | 0.0176 (11) | 0.0312 (12) | −0.0004 (9) | −0.0003 (9) | 0.0023 (9) |
N6 | 0.0513 (14) | 0.0236 (11) | 0.0295 (12) | 0.0080 (10) | 0.0083 (10) | 0.0043 (9) |
C1X | 0.0539 (19) | 0.0540 (18) | 0.0411 (17) | −0.0214 (15) | −0.0026 (14) | 0.0134 (14) |
O2X | 0.0555 (13) | 0.0488 (12) | 0.0413 (12) | −0.0021 (10) | 0.0125 (10) | −0.0153 (9) |
C4X | 0.0497 (17) | 0.0327 (14) | 0.0461 (17) | −0.0003 (12) | −0.0026 (13) | 0.0050 (12) |
C5X | 0.0460 (17) | 0.0515 (18) | 0.058 (2) | −0.0007 (14) | 0.0153 (15) | −0.0235 (15) |
C2X | 0.031 (2) | 0.035 (3) | 0.031 (3) | −0.006 (2) | 0.003 (2) | 0.004 (2) |
N3X | 0.037 (2) | 0.032 (3) | 0.035 (3) | −0.0038 (19) | 0.0029 (19) | −0.002 (2) |
C2X' | 0.030 (3) | 0.027 (4) | 0.030 (4) | 0.000 (3) | 0.004 (3) | −0.008 (3) |
N3X' | 0.038 (3) | 0.027 (3) | 0.031 (4) | 0.001 (2) | 0.010 (2) | −0.004 (3) |
Geometric parameters (Å, º) top
N1—C2 | 1.364 (3) | C1X—H4XC | 0.9799 |
N1—C6 | 1.374 (3) | O2X—C2X | 1.256 (6) |
N1—H1 | 0.875 (18) | O2X—C2X' | 1.296 (6) |
C2—O2 | 1.223 (3) | C4X—N3X | 1.502 (6) |
C2—N3 | 1.360 (3) | C4X—C2X' | 1.512 (6) |
N3—C4 | 1.387 (3) | C4X—H4X1 | 0.9800 |
N3—H3 | 0.872 (14) | C4X—H4X2 | 0.9800 |
C4—O4 | 1.256 (3) | C4X—H4X3 | 0.9800 |
C4—C5 | 1.400 (3) | C4X—H1XA | 0.9799 |
C5—C6 | 1.376 (3) | C4X—H1XB | 0.9801 |
C5—H5 | 0.9500 | C4X—H1XC | 0.9799 |
C6—N6 | 1.325 (3) | C5X—N3X' | 1.478 (5) |
N6—H61 | 0.92 (3) | C5X—N3X | 1.524 (6) |
N6—H62 | 0.87 (3) | C5X—H5X1 | 0.9800 |
C1X—C2X | 1.497 (6) | C5X—H5X2 | 0.9800 |
C1X—N3X' | 1.538 (6) | C5X—H5X3 | 0.9800 |
C1X—H1X1 | 0.9800 | C5X—H5XA | 0.9800 |
C1X—H1X2 | 0.9800 | C5X—H5XB | 0.9800 |
C1X—H1X3 | 0.9800 | C5X—H5XC | 0.9801 |
C1X—H4XA | 0.9800 | C2X—N3X | 1.326 (8) |
C1X—H4XB | 0.9799 | C2X'—N3X' | 1.327 (8) |
| | | |
C2—N1—C6 | 123.8 (2) | N3X—C4X—H1XA | 74.6 |
C2—N1—H1 | 116.8 (18) | C2X'—C4X—H1XA | 109.6 |
C6—N1—H1 | 119.1 (18) | H4X2—C4X—H1XA | 125.4 |
O2—C2—N3 | 122.9 (2) | H4X3—C4X—H1XA | 120.4 |
O2—C2—N1 | 122.0 (2) | N3X—C4X—H1XB | 121.1 |
N3—C2—N1 | 115.08 (19) | C2X'—C4X—H1XB | 109.3 |
C2—N3—C4 | 125.3 (2) | H4X1—C4X—H1XB | 89.0 |
C2—N3—H3 | 116.3 (19) | H4X3—C4X—H1XB | 115.9 |
C4—N3—H3 | 118.3 (19) | H1XA—C4X—H1XB | 109.5 |
O4—C4—N3 | 117.7 (2) | N3X—C4X—H1XC | 124.7 |
O4—C4—C5 | 125.5 (2) | C2X'—C4X—H1XC | 109.5 |
N3—C4—C5 | 116.8 (2) | H4X1—C4X—H1XC | 91.3 |
C6—C5—C4 | 119.7 (2) | H4X2—C4X—H1XC | 110.4 |
C6—C5—H5 | 120.2 | H1XA—C4X—H1XC | 109.5 |
C4—C5—H5 | 120.2 | H1XB—C4X—H1XC | 109.5 |
N6—C6—N1 | 115.3 (2) | N3X'—C5X—H5X1 | 143.8 |
N6—C6—C5 | 125.4 (2) | N3X—C5X—H5X1 | 109.5 |
N1—C6—C5 | 119.3 (2) | N3X'—C5X—H5X2 | 92.0 |
C6—N6—H61 | 118 (2) | N3X—C5X—H5X2 | 109.5 |
C6—N6—H62 | 121 (2) | H5X1—C5X—H5X2 | 109.5 |
H61—N6—H62 | 120 (3) | N3X'—C5X—H5X3 | 89.0 |
C2X—C1X—H1X1 | 109.5 | N3X—C5X—H5X3 | 109.5 |
N3X'—C1X—H1X1 | 70.5 | H5X1—C5X—H5X3 | 109.5 |
C2X—C1X—H1X2 | 109.5 | H5X2—C5X—H5X3 | 109.5 |
N3X'—C1X—H1X2 | 123.6 | N3X'—C5X—H5XA | 109.6 |
H1X1—C1X—H1X2 | 109.5 | N3X—C5X—H5XA | 143.8 |
C2X—C1X—H1X3 | 109.5 | H5X1—C5X—H5XA | 106.1 |
N3X'—C1X—H1X3 | 123.9 | H5X2—C5X—H5XA | 63.8 |
H1X1—C1X—H1X3 | 109.5 | H5X3—C5X—H5XA | 50.1 |
H1X2—C1X—H1X3 | 109.5 | N3X'—C5X—H5XB | 109.4 |
C2X—C1X—H4XA | 148.6 | N3X—C5X—H5XB | 88.0 |
N3X'—C1X—H4XA | 109.6 | H5X1—C5X—H5XB | 50.9 |
H1X2—C1X—H4XA | 87.4 | H5X2—C5X—H5XB | 158.4 |
H1X3—C1X—H4XA | 88.1 | H5X3—C5X—H5XB | 74.7 |
C2X—C1X—H4XB | 87.6 | H5XA—C5X—H5XB | 109.5 |
N3X'—C1X—H4XB | 109.3 | N3X'—C5X—H5XC | 109.4 |
H1X1—C1X—H4XB | 124.2 | N3X—C5X—H5XC | 93.0 |
H1X3—C1X—H4XB | 113.8 | H5X1—C5X—H5XC | 63.0 |
H4XA—C1X—H4XB | 109.5 | H5X2—C5X—H5XC | 58.5 |
C2X—C1X—H4XC | 87.9 | H5X3—C5X—H5XC | 157.4 |
N3X'—C1X—H4XC | 109.5 | H5XA—C5X—H5XC | 109.5 |
H1X1—C1X—H4XC | 123.4 | H5XB—C5X—H5XC | 109.5 |
H1X2—C1X—H4XC | 114.4 | O2X—C2X—N3X | 113.7 (5) |
H4XA—C1X—H4XC | 109.5 | O2X—C2X—C1X | 131.7 (5) |
H4XB—C1X—H4XC | 109.5 | N3X—C2X—C1X | 114.6 (5) |
N3X—C4X—H4X1 | 109.5 | C2X—N3X—C4X | 118.5 (5) |
C2X'—C4X—H4X1 | 144.5 | C2X—N3X—C5X | 119.7 (5) |
N3X—C4X—H4X2 | 109.5 | C4X—N3X—C5X | 121.4 (4) |
C2X'—C4X—H4X2 | 90.3 | O2X—C2X'—N3X' | 115.6 (5) |
H4X1—C4X—H4X2 | 109.5 | O2X—C2X'—C4X | 130.7 (5) |
N3X—C4X—H4X3 | 109.5 | N3X'—C2X'—C4X | 113.7 (5) |
C2X'—C4X—H4X3 | 90.0 | C2X'—N3X'—C5X | 118.3 (5) |
H4X1—C4X—H4X3 | 109.5 | C2X'—N3X'—C1X | 113.6 (5) |
H4X2—C4X—H4X3 | 109.5 | C5X—N3X'—C1X | 128.1 (4) |
| | | |
C6—N1—C2—O2 | −177.9 (2) | O2X—C2X—N3X—C5X | −174.0 (3) |
C6—N1—C2—N3 | 2.5 (3) | C1X—C2X—N3X—C5X | 7.7 (5) |
O2—C2—N3—C4 | 179.7 (2) | C2X'—C4X—N3X—C2X | −0.5 (5) |
N1—C2—N3—C4 | −0.7 (4) | C2X'—C4X—N3X—C5X | 172.1 (6) |
C2—N3—C4—O4 | −179.6 (2) | N3X'—C5X—N3X—C2X | −3.1 (4) |
C2—N3—C4—C5 | 0.1 (3) | N3X'—C5X—N3X—C4X | −175.7 (7) |
O4—C4—C5—C6 | 178.4 (2) | C2X—O2X—C2X'—N3X' | 0.8 (4) |
N3—C4—C5—C6 | −1.3 (3) | C2X—O2X—C2X'—C4X | −178.5 (9) |
C2—N1—C6—N6 | 176.6 (2) | N3X—C4X—C2X'—O2X | 177.5 (9) |
C2—N1—C6—C5 | −3.7 (4) | N3X—C4X—C2X'—N3X' | −1.8 (4) |
C4—C5—C6—N6 | −177.3 (2) | O2X—C2X'—N3X'—C5X | 176.1 (4) |
C4—C5—C6—N1 | 3.0 (4) | C4X—C2X'—N3X'—C5X | −4.5 (7) |
C2X'—O2X—C2X—N3X | 1.4 (4) | O2X—C2X'—N3X'—C1X | −1.8 (7) |
C2X'—O2X—C2X—C1X | 179.3 (8) | C4X—C2X'—N3X'—C1X | 177.6 (4) |
N3X'—C1X—C2X—O2X | 179.4 (7) | N3X—C5X—N3X'—C2X' | 5.0 (4) |
N3X'—C1X—C2X—N3X | −2.7 (4) | N3X—C5X—N3X'—C1X | −177.4 (8) |
O2X—C2X—N3X—C4X | −1.2 (6) | C2X—C1X—N3X'—C2X' | 0.7 (4) |
C1X—C2X—N3X—C4X | −179.5 (3) | C2X—C1X—N3X'—C5X | −176.9 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2X | 0.88 (2) | 1.93 (2) | 2.738 (3) | 153 (3) |
N3—H3···O4i | 0.87 (1) | 1.93 (2) | 2.796 (3) | 175 (3) |
N6—H61···O2X | 0.92 (3) | 2.07 (3) | 2.885 (3) | 147 (3) |
N6—H62···O4ii | 0.87 (3) | 1.99 (3) | 2.842 (3) | 168 (3) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z+1/2. |
(Ib) 6-Aminouracil dimethylacetamide monosolvate
top
Crystal data top
C4H5N3O2·C4H9NO | F(000) = 912 |
Mr = 214.23 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6388 reflections |
a = 7.1200 (7) Å | θ = 3.3–26.0° |
b = 21.882 (3) Å | µ = 0.11 mm−1 |
c = 13.1561 (14) Å | T = 173 K |
β = 92.908 (8)° | Block, colourless |
V = 2047.1 (4) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 8 | |
Data collection top
Stoe IPDS II two-circle diffractometer | 3823 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 2098 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.062 |
ω scans | θmax = 25.6°, θmin = 3.3° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −8→8 |
Tmin = 0.968, Tmax = 0.979 | k = −26→25 |
11142 measured reflections | l = −15→13 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.085P)2] where P = (Fo2 + 2Fc2)/3 |
3823 reflections | (Δ/σ)max < 0.001 |
336 parameters | Δρmax = 0.32 e Å−3 |
23 restraints | Δρmin = −0.32 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 | Occ. (<1) |
N1A | 0.4153 (3) | 0.05272 (13) | 0.3919 (2) | 0.0249 (6) | |
H1A | 0.397 (5) | 0.0153 (18) | 0.381 (3) | 0.030* | |
C2A | 0.2669 (4) | 0.09028 (15) | 0.4043 (3) | 0.0244 (7) | |
O2A | 0.1051 (3) | 0.07105 (11) | 0.4039 (2) | 0.0344 (6) | |
N3A | 0.3101 (3) | 0.15044 (12) | 0.4166 (2) | 0.0253 (6) | |
H3A | 0.221 (4) | 0.1767 (13) | 0.421 (3) | 0.030* | |
C4A | 0.4902 (4) | 0.17479 (15) | 0.4155 (3) | 0.0252 (7) | |
O4A | 0.5049 (3) | 0.23125 (10) | 0.4273 (2) | 0.0341 (6) | |
C5A | 0.6367 (4) | 0.13355 (15) | 0.4005 (3) | 0.0251 (7) | |
H5A | 0.7624 | 0.1478 | 0.3981 | 0.030* | |
C6A | 0.5979 (4) | 0.07243 (15) | 0.3894 (3) | 0.0265 (8) | |
N6A | 0.7262 (4) | 0.02904 (14) | 0.3746 (3) | 0.0362 (8) | |
H61A | 0.844 (6) | 0.0431 (18) | 0.381 (3) | 0.043* | |
H62A | 0.691 (5) | −0.010 (2) | 0.371 (3) | 0.043* | |
N1B | 0.9085 (3) | 0.40713 (13) | 0.3952 (2) | 0.0253 (6) | |
H1B | 0.885 (5) | 0.4453 (18) | 0.383 (3) | 0.030* | |
C2B | 0.7615 (4) | 0.36816 (15) | 0.4083 (3) | 0.0232 (7) | |
O2B | 0.5996 (3) | 0.38757 (10) | 0.4116 (2) | 0.0328 (6) | |
N3B | 0.8062 (3) | 0.30841 (12) | 0.4175 (2) | 0.0252 (7) | |
H3B | 0.715 (4) | 0.2810 (13) | 0.423 (3) | 0.030* | |
C4B | 0.9882 (4) | 0.28439 (15) | 0.4146 (3) | 0.0255 (8) | |
O4B | 1.0040 (3) | 0.22820 (10) | 0.4231 (2) | 0.0370 (7) | |
C5B | 1.1326 (4) | 0.32690 (15) | 0.4014 (3) | 0.0263 (8) | |
H5B | 1.2593 | 0.3134 | 0.3997 | 0.032* | |
C6B | 1.0916 (4) | 0.38732 (15) | 0.3909 (3) | 0.0235 (7) | |
N6B | 1.2174 (4) | 0.43128 (14) | 0.3744 (3) | 0.0328 (7) | |
H61B | 1.334 (6) | 0.4205 (18) | 0.371 (3) | 0.039* | |
H62B | 1.190 (5) | 0.4687 (19) | 0.363 (3) | 0.039* | |
C1X | 1.0261 (5) | 0.63621 (18) | 0.3249 (3) | 0.0432 (10) | |
H11X | 0.9554 | 0.6746 | 0.3203 | 0.065* | 0.734 (10) |
H12X | 1.0843 | 0.6285 | 0.2602 | 0.065* | 0.734 (10) |
H13X | 1.1242 | 0.6392 | 0.3797 | 0.065* | 0.734 (10) |
H4AX | 1.0695 | 0.6662 | 0.3762 | 0.065* | 0.266 (10) |
H4BX | 1.0380 | 0.6534 | 0.2568 | 0.065* | 0.266 (10) |
H4CX | 1.1029 | 0.5991 | 0.3321 | 0.065* | 0.266 (10) |
O2X | 0.9428 (4) | 0.52995 (12) | 0.3574 (2) | 0.0463 (7) | |
C4X | 0.5815 (5) | 0.54814 (19) | 0.3741 (3) | 0.0451 (10) | |
H41X | 0.4541 | 0.5648 | 0.3765 | 0.068* | 0.734 (10) |
H42X | 0.6176 | 0.5289 | 0.4394 | 0.068* | 0.734 (10) |
H43X | 0.5847 | 0.5176 | 0.3197 | 0.068* | 0.734 (10) |
H1AX | 0.5646 | 0.5045 | 0.3875 | 0.068* | 0.266 (10) |
H1BX | 0.5059 | 0.5597 | 0.3128 | 0.068* | 0.266 (10) |
H1CX | 0.5411 | 0.5719 | 0.4322 | 0.068* | 0.266 (10) |
N3X | 0.7104 (5) | 0.59645 (17) | 0.3544 (3) | 0.0305 (13) | 0.734 (10) |
C2X | 0.8918 (6) | 0.5834 (2) | 0.3477 (4) | 0.0272 (13) | 0.734 (10) |
C5X | 0.6305 (8) | 0.6582 (2) | 0.3530 (4) | 0.0351 (14) | 0.734 (10) |
H51X | 0.4940 | 0.6556 | 0.3588 | 0.053* | 0.734 (10) |
H52X | 0.6579 | 0.6784 | 0.2890 | 0.053* | 0.734 (10) |
H53X | 0.6861 | 0.6817 | 0.4104 | 0.053* | 0.734 (10) |
N3X' | 0.8343 (18) | 0.6214 (7) | 0.3389 (12) | 0.062 (5)* | 0.266 (10) |
C2X' | 0.7903 (8) | 0.5611 (4) | 0.3579 (15) | 0.061 (6)* | 0.266 (10) |
C5X' | 0.715 (3) | 0.6753 (8) | 0.3421 (14) | 0.051 (5)* | 0.266 (10) |
H5AX | 0.7868 | 0.7115 | 0.3241 | 0.077* | 0.266 (10) |
H5BX | 0.6697 | 0.6802 | 0.4108 | 0.077* | 0.266 (10) |
H5CX | 0.6069 | 0.6704 | 0.2934 | 0.077* | 0.266 (10) |
C1Y | 0.5534 (5) | −0.17677 (18) | 0.3162 (3) | 0.0424 (10) | |
H11Y | 0.4869 | −0.2159 | 0.3114 | 0.064* | 0.582 (12) |
H12Y | 0.6516 | −0.1787 | 0.3710 | 0.064* | 0.582 (12) |
H13Y | 0.6110 | −0.1682 | 0.2515 | 0.064* | 0.582 (12) |
H4AY | 0.6045 | −0.2061 | 0.3667 | 0.064* | 0.418 (12) |
H4BY | 0.6236 | −0.1383 | 0.3226 | 0.064* | 0.418 (12) |
H4CY | 0.5651 | −0.1935 | 0.2477 | 0.064* | 0.418 (12) |
O2Y | 0.4495 (4) | −0.06969 (12) | 0.3494 (2) | 0.0471 (7) | |
C4Y | 0.1021 (5) | −0.0940 (2) | 0.3677 (3) | 0.0452 (10) | |
H41Y | −0.0243 | −0.1117 | 0.3685 | 0.068* | 0.582 (12) |
H42Y | 0.1032 | −0.0615 | 0.3166 | 0.068* | 0.582 (12) |
H43Y | 0.1373 | −0.0771 | 0.4350 | 0.068* | 0.582 (12) |
H1AY | 0.0285 | −0.1045 | 0.3052 | 0.068* | 0.418 (12) |
H1BY | 0.0849 | −0.0506 | 0.3832 | 0.068* | 0.418 (12) |
H1CY | 0.0595 | −0.1189 | 0.4241 | 0.068* | 0.418 (12) |
N3Y | 0.2337 (9) | −0.1406 (3) | 0.3431 (4) | 0.033 (2) | 0.582 (12) |
C2Y | 0.4136 (10) | −0.1256 (4) | 0.3388 (5) | 0.030 (2) | 0.582 (12) |
C5Y | 0.1674 (15) | −0.2047 (6) | 0.3453 (13) | 0.044 (3) | 0.582 (12) |
H51Y | 0.0310 | −0.2053 | 0.3522 | 0.067* | 0.582 (12) |
H52Y | 0.2297 | −0.2259 | 0.4033 | 0.067* | 0.582 (12) |
H53Y | 0.1977 | −0.2252 | 0.2820 | 0.067* | 0.582 (12) |
N3Y' | 0.3572 (12) | −0.1656 (4) | 0.3332 (5) | 0.032 (3) | 0.418 (12) |
C2Y' | 0.3110 (7) | −0.1067 (3) | 0.3532 (8) | 0.035 (3) | 0.418 (12) |
C5Y' | 0.239 (2) | −0.2184 (8) | 0.3394 (15) | 0.042 (4) | 0.418 (12) |
H5AY | 0.2775 | −0.2492 | 0.2905 | 0.063* | 0.418 (12) |
H5BY | 0.1081 | −0.2067 | 0.3235 | 0.063* | 0.418 (12) |
H5CY | 0.2512 | −0.2353 | 0.4084 | 0.063* | 0.418 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0197 (12) | 0.0203 (15) | 0.0345 (17) | −0.0020 (11) | 0.0000 (11) | −0.0014 (13) |
C2A | 0.0198 (14) | 0.0256 (18) | 0.0278 (19) | −0.0047 (13) | 0.0000 (13) | −0.0007 (15) |
O2A | 0.0180 (10) | 0.0317 (14) | 0.0536 (17) | −0.0049 (10) | 0.0031 (10) | −0.0028 (12) |
N3A | 0.0167 (12) | 0.0222 (15) | 0.0369 (17) | 0.0020 (11) | 0.0006 (11) | 0.0003 (13) |
C4A | 0.0198 (14) | 0.0247 (19) | 0.0311 (19) | −0.0036 (13) | 0.0017 (13) | 0.0034 (15) |
O4A | 0.0221 (11) | 0.0217 (14) | 0.0587 (17) | −0.0026 (9) | 0.0040 (11) | −0.0011 (12) |
C5A | 0.0175 (13) | 0.0228 (17) | 0.035 (2) | −0.0018 (13) | 0.0012 (13) | −0.0004 (15) |
C6A | 0.0183 (14) | 0.0301 (19) | 0.031 (2) | −0.0017 (13) | −0.0009 (13) | −0.0018 (15) |
N6A | 0.0174 (13) | 0.0257 (17) | 0.066 (2) | 0.0017 (12) | 0.0028 (13) | −0.0041 (16) |
N1B | 0.0207 (12) | 0.0183 (14) | 0.0368 (18) | 0.0040 (11) | 0.0016 (11) | 0.0011 (13) |
C2B | 0.0193 (14) | 0.0239 (18) | 0.0265 (19) | −0.0003 (13) | 0.0015 (12) | −0.0020 (14) |
O2B | 0.0190 (10) | 0.0294 (13) | 0.0502 (17) | 0.0048 (10) | 0.0032 (10) | −0.0022 (12) |
N3B | 0.0158 (12) | 0.0235 (16) | 0.0366 (18) | 0.0005 (11) | 0.0039 (11) | 0.0013 (13) |
C4B | 0.0210 (14) | 0.0228 (19) | 0.033 (2) | 0.0040 (13) | 0.0013 (13) | 0.0003 (15) |
O4B | 0.0243 (11) | 0.0222 (14) | 0.0649 (19) | 0.0023 (10) | 0.0065 (11) | 0.0041 (12) |
C5B | 0.0175 (14) | 0.0272 (19) | 0.034 (2) | 0.0040 (13) | 0.0014 (13) | −0.0012 (15) |
C6B | 0.0151 (13) | 0.0292 (18) | 0.0261 (19) | −0.0023 (13) | 0.0015 (12) | −0.0012 (15) |
N6B | 0.0181 (13) | 0.0231 (16) | 0.057 (2) | 0.0021 (12) | 0.0029 (13) | 0.0049 (15) |
C1X | 0.048 (2) | 0.033 (2) | 0.049 (3) | −0.0074 (17) | −0.0014 (18) | −0.0013 (18) |
O2X | 0.0461 (15) | 0.0307 (16) | 0.062 (2) | 0.0087 (12) | 0.0020 (13) | 0.0030 (14) |
C4X | 0.0326 (18) | 0.051 (3) | 0.052 (3) | −0.0010 (18) | 0.0079 (17) | 0.000 (2) |
N3X | 0.032 (2) | 0.023 (2) | 0.036 (3) | −0.0005 (17) | 0.0029 (17) | −0.0033 (18) |
C2X | 0.039 (3) | 0.015 (3) | 0.028 (3) | 0.003 (2) | −0.002 (2) | −0.003 (2) |
C5X | 0.036 (3) | 0.026 (3) | 0.043 (3) | 0.007 (2) | 0.002 (2) | −0.002 (2) |
C1Y | 0.0404 (19) | 0.035 (2) | 0.053 (3) | 0.0059 (17) | 0.0086 (18) | 0.0030 (19) |
O2Y | 0.0565 (17) | 0.0223 (15) | 0.062 (2) | −0.0104 (12) | −0.0002 (14) | −0.0036 (13) |
C4Y | 0.0336 (19) | 0.057 (3) | 0.045 (3) | −0.0005 (18) | 0.0070 (17) | −0.009 (2) |
N3Y | 0.036 (4) | 0.030 (4) | 0.034 (3) | 0.001 (3) | 0.005 (2) | −0.002 (3) |
C2Y | 0.033 (4) | 0.027 (5) | 0.030 (4) | −0.001 (3) | 0.003 (3) | −0.002 (3) |
C5Y | 0.046 (6) | 0.041 (6) | 0.046 (6) | −0.026 (5) | −0.005 (6) | 0.002 (5) |
N3Y' | 0.047 (6) | 0.018 (5) | 0.032 (4) | −0.009 (4) | 0.006 (3) | −0.003 (3) |
C2Y' | 0.036 (6) | 0.028 (7) | 0.043 (6) | 0.005 (5) | 0.003 (4) | −0.003 (4) |
C5Y' | 0.054 (10) | 0.038 (9) | 0.033 (6) | −0.025 (7) | 0.001 (8) | 0.010 (6) |
Geometric parameters (Å, º) top
N1A—C2A | 1.355 (4) | C4X—H43X | 0.9800 |
N1A—C6A | 1.372 (4) | C4X—H1AX | 0.9800 |
N1A—H1A | 0.84 (4) | C4X—H1BX | 0.9800 |
C2A—O2A | 1.226 (4) | C4X—H1CX | 0.9800 |
C2A—N3A | 1.360 (4) | N3X—C2X | 1.330 (6) |
N3A—C4A | 1.389 (4) | N3X—C5X | 1.465 (6) |
N3A—H3A | 0.862 (18) | C5X—H51X | 0.9800 |
C4A—O4A | 1.249 (4) | C5X—H52X | 0.9800 |
C4A—C5A | 1.401 (4) | C5X—H53X | 0.9800 |
C5A—C6A | 1.372 (5) | N3X'—C2X' | 1.382 (14) |
C5A—H5A | 0.9500 | N3X'—C5X' | 1.46 (2) |
C6A—N6A | 1.339 (4) | C5X'—H5AX | 0.9800 |
N6A—H61A | 0.89 (4) | C5X'—H5BX | 0.9800 |
N6A—H62A | 0.89 (4) | C5X'—H5CX | 0.9800 |
N1B—C2B | 1.368 (4) | C1Y—N3Y' | 1.447 (9) |
N1B—C6B | 1.377 (4) | C1Y—C2Y | 1.537 (8) |
N1B—H1B | 0.86 (4) | C1Y—H11Y | 0.9800 |
C2B—O2B | 1.231 (4) | C1Y—H12Y | 0.9800 |
C2B—N3B | 1.350 (4) | C1Y—H13Y | 0.9800 |
N3B—C4B | 1.401 (4) | C1Y—H4AY | 0.9800 |
N3B—H3B | 0.888 (18) | C1Y—H4BY | 0.9800 |
C4B—O4B | 1.239 (4) | C1Y—H4CY | 0.9800 |
C4B—C5B | 1.404 (4) | O2Y—C2Y | 1.256 (8) |
C5B—C6B | 1.360 (5) | O2Y—C2Y' | 1.279 (5) |
C5B—H5B | 0.9500 | C4Y—N3Y | 1.433 (7) |
C6B—N6B | 1.340 (4) | C4Y—C2Y' | 1.535 (5) |
N6B—H61B | 0.87 (4) | C4Y—H41Y | 0.9800 |
N6B—H62B | 0.85 (4) | C4Y—H42Y | 0.9800 |
C1X—N3X' | 1.425 (13) | C4Y—H43Y | 0.9800 |
C1X—C2X | 1.539 (6) | C4Y—H1AY | 0.9800 |
C1X—H11X | 0.9800 | C4Y—H1BY | 0.9800 |
C1X—H12X | 0.9800 | C4Y—H1CY | 0.9800 |
C1X—H13X | 0.9800 | N3Y—C2Y | 1.326 (10) |
C1X—H4AX | 0.9800 | N3Y—C5Y | 1.480 (15) |
C1X—H4BX | 0.9800 | C5Y—H51Y | 0.9800 |
C1X—H4CX | 0.9800 | C5Y—H52Y | 0.9800 |
O2X—C2X | 1.230 (5) | C5Y—H53Y | 0.9800 |
O2X—C2X' | 1.283 (5) | N3Y'—C2Y' | 1.359 (11) |
C4X—N3X | 1.432 (5) | N3Y'—C5Y' | 1.433 (19) |
C4X—C2X' | 1.539 (5) | C5Y'—H5AY | 0.9800 |
C4X—H41X | 0.9800 | C5Y'—H5BY | 0.9800 |
C4X—H42X | 0.9800 | C5Y'—H5CY | 0.9800 |
| | | |
C2A—N1A—C6A | 123.9 (3) | O2X—C2X—N3X | 118.6 (4) |
C2A—N1A—H1A | 120 (2) | O2X—C2X—C1X | 123.5 (4) |
C6A—N1A—H1A | 116 (2) | N3X—C2X—C1X | 117.9 (4) |
O2A—C2A—N1A | 122.0 (3) | N3X—C5X—H51X | 109.5 |
O2A—C2A—N3A | 122.7 (3) | N3X—C5X—H52X | 109.5 |
N1A—C2A—N3A | 115.4 (3) | H51X—C5X—H52X | 109.5 |
C2A—N3A—C4A | 125.0 (3) | N3X—C5X—H53X | 109.5 |
C2A—N3A—H3A | 119 (2) | H51X—C5X—H53X | 109.5 |
C4A—N3A—H3A | 116 (2) | H52X—C5X—H53X | 109.5 |
O4A—C4A—N3A | 116.7 (3) | C2X'—N3X'—C1X | 117.9 (10) |
O4A—C4A—C5A | 126.6 (3) | C2X'—N3X'—C5X' | 129.0 (12) |
N3A—C4A—C5A | 116.7 (3) | C1X—N3X'—C5X' | 112.7 (12) |
C6A—C5A—C4A | 119.7 (3) | O2X—C2X'—N3X' | 107.9 (8) |
C6A—C5A—H5A | 120.1 | O2X—C2X'—C4X | 136.6 (8) |
C4A—C5A—H5A | 120.1 | N3X'—C2X'—C4X | 115.5 (7) |
N6A—C6A—N1A | 115.8 (3) | N3X'—C5X'—H5AX | 109.5 |
N6A—C6A—C5A | 124.9 (3) | N3X'—C5X'—H5BX | 109.5 |
N1A—C6A—C5A | 119.3 (3) | H5AX—C5X'—H5BX | 109.5 |
C6A—N6A—H61A | 113 (3) | N3X'—C5X'—H5CX | 109.5 |
C6A—N6A—H62A | 120 (2) | H5AX—C5X'—H5CX | 109.5 |
H61A—N6A—H62A | 126 (4) | H5BX—C5X'—H5CX | 109.5 |
C2B—N1B—C6B | 122.7 (3) | N3Y'—C1Y—H11Y | 71.9 |
C2B—N1B—H1B | 119 (2) | C2Y—C1Y—H11Y | 109.5 |
C6B—N1B—H1B | 118 (2) | N3Y'—C1Y—H12Y | 123.4 |
O2B—C2B—N3B | 123.2 (3) | C2Y—C1Y—H12Y | 109.5 |
O2B—C2B—N1B | 120.9 (3) | H11Y—C1Y—H12Y | 109.5 |
N3B—C2B—N1B | 115.9 (3) | N3Y'—C1Y—H13Y | 123.5 |
C2B—N3B—C4B | 125.1 (3) | C2Y—C1Y—H13Y | 109.5 |
C2B—N3B—H3B | 120 (2) | H11Y—C1Y—H13Y | 109.5 |
C4B—N3B—H3B | 115 (2) | H12Y—C1Y—H13Y | 109.5 |
O4B—C4B—N3B | 116.7 (3) | N3Y'—C1Y—H4AY | 109.5 |
O4B—C4B—C5B | 127.2 (3) | C2Y—C1Y—H4AY | 124.5 |
N3B—C4B—C5B | 116.1 (3) | H11Y—C1Y—H4AY | 68.4 |
C6B—C5B—C4B | 120.1 (3) | H13Y—C1Y—H4AY | 123.7 |
C6B—C5B—H5B | 119.9 | N3Y'—C1Y—H4BY | 109.5 |
C4B—C5B—H5B | 119.9 | C2Y—C1Y—H4BY | 71.9 |
N6B—C6B—C5B | 124.9 (3) | H11Y—C1Y—H4BY | 177.9 |
N6B—C6B—N1B | 115.0 (3) | H12Y—C1Y—H4BY | 68.4 |
C5B—C6B—N1B | 120.1 (3) | H13Y—C1Y—H4BY | 71.2 |
C6B—N6B—H61B | 118 (3) | H4AY—C1Y—H4BY | 109.5 |
C6B—N6B—H62B | 125 (3) | N3Y'—C1Y—H4CY | 109.5 |
H61B—N6B—H62B | 118 (4) | C2Y—C1Y—H4CY | 122.4 |
N3X'—C1X—H11X | 73.1 | H11Y—C1Y—H4CY | 71.2 |
C2X—C1X—H11X | 109.5 | H12Y—C1Y—H4CY | 124.8 |
N3X'—C1X—H12X | 121.5 | H4AY—C1Y—H4CY | 109.5 |
C2X—C1X—H12X | 109.5 | H4BY—C1Y—H4CY | 109.5 |
H11X—C1X—H12X | 109.5 | N3Y—C4Y—H41Y | 109.5 |
N3X'—C1X—H13X | 124.9 | C2Y'—C4Y—H41Y | 145.7 |
C2X—C1X—H13X | 109.5 | N3Y—C4Y—H42Y | 109.5 |
H11X—C1X—H13X | 109.5 | C2Y'—C4Y—H42Y | 90.2 |
H12X—C1X—H13X | 109.5 | H41Y—C4Y—H42Y | 109.5 |
N3X'—C1X—H4AX | 109.5 | N3Y—C4Y—H43Y | 109.5 |
C2X—C1X—H4AX | 123.1 | C2Y'—C4Y—H43Y | 88.6 |
H11X—C1X—H4AX | 67.1 | H41Y—C4Y—H43Y | 109.5 |
H12X—C1X—H4AX | 125.6 | H42Y—C4Y—H43Y | 109.5 |
N3X'—C1X—H4BX | 109.5 | N3Y—C4Y—H1AY | 88.4 |
C2X—C1X—H4BX | 123.4 | C2Y'—C4Y—H1AY | 109.5 |
H11X—C1X—H4BX | 71.4 | H41Y—C4Y—H1AY | 57.6 |
H13X—C1X—H4BX | 123.8 | H42Y—C4Y—H1AY | 67.4 |
H4AX—C1X—H4BX | 109.5 | H43Y—C4Y—H1AY | 161.4 |
N3X'—C1X—H4CX | 109.5 | N3Y—C4Y—H1BY | 145.7 |
C2X—C1X—H4CX | 73.1 | C2Y'—C4Y—H1BY | 109.5 |
H11X—C1X—H4CX | 176.4 | H41Y—C4Y—H1BY | 104.8 |
H12X—C1X—H4CX | 71.5 | H42Y—C4Y—H1BY | 56.2 |
H13X—C1X—H4CX | 67.1 | H43Y—C4Y—H1BY | 58.3 |
H4AX—C1X—H4CX | 109.5 | H1AY—C4Y—H1BY | 109.5 |
H4BX—C1X—H4CX | 109.5 | N3Y—C4Y—H1CY | 90.5 |
N3X—C4X—H41X | 109.5 | C2Y'—C4Y—H1CY | 109.5 |
C2X'—C4X—H41X | 146.9 | H41Y—C4Y—H1CY | 56.9 |
N3X—C4X—H42X | 109.5 | H42Y—C4Y—H1CY | 159.4 |
C2X'—C4X—H42X | 89.3 | H43Y—C4Y—H1CY | 66.5 |
H41X—C4X—H42X | 109.5 | H1AY—C4Y—H1CY | 109.5 |
N3X—C4X—H43X | 109.5 | H1BY—C4Y—H1CY | 109.5 |
C2X'—C4X—H43X | 88.1 | C2Y—N3Y—C4Y | 118.6 (6) |
H41X—C4X—H43X | 109.5 | C2Y—N3Y—C5Y | 123.0 (7) |
H42X—C4X—H43X | 109.5 | C4Y—N3Y—C5Y | 117.2 (6) |
N3X—C4X—H1AX | 146.9 | O2Y—C2Y—N3Y | 115.3 (6) |
C2X'—C4X—H1AX | 109.5 | O2Y—C2Y—C1Y | 126.9 (6) |
H41X—C4X—H1AX | 103.6 | N3Y—C2Y—C1Y | 117.7 (7) |
H42X—C4X—H1AX | 56.8 | N3Y—C5Y—H51Y | 109.5 |
H43X—C4X—H1AX | 58.3 | N3Y—C5Y—H52Y | 109.5 |
N3X—C4X—H1BX | 89.5 | H51Y—C5Y—H52Y | 109.5 |
C2X'—C4X—H1BX | 109.5 | N3Y—C5Y—H53Y | 109.5 |
H41X—C4X—H1BX | 57.2 | H51Y—C5Y—H53Y | 109.5 |
H42X—C4X—H1BX | 160.4 | H52Y—C5Y—H53Y | 109.5 |
H43X—C4X—H1BX | 66.9 | C2Y'—N3Y'—C5Y' | 127.2 (9) |
H1AX—C4X—H1BX | 109.5 | C2Y'—N3Y'—C1Y | 115.8 (7) |
N3X—C4X—H1CX | 88.0 | C5Y'—N3Y'—C1Y | 116.5 (8) |
C2X'—C4X—H1CX | 109.5 | O2Y—C2Y'—N3Y' | 113.5 (6) |
H41X—C4X—H1CX | 57.9 | O2Y—C2Y'—C4Y | 130.1 (6) |
H42X—C4X—H1CX | 67.5 | N3Y'—C2Y'—C4Y | 116.2 (6) |
H43X—C4X—H1CX | 161.8 | N3Y'—C5Y'—H5AY | 109.5 |
H1AX—C4X—H1CX | 109.5 | N3Y'—C5Y'—H5BY | 109.5 |
H1BX—C4X—H1CX | 109.5 | H5AY—C5Y'—H5BY | 109.5 |
C2X—N3X—C4X | 119.2 (4) | N3Y'—C5Y'—H5CY | 109.5 |
C2X—N3X—C5X | 125.1 (4) | H5AY—C5Y'—H5CY | 109.5 |
C4X—N3X—C5X | 115.5 (4) | H5BY—C5Y'—H5CY | 109.5 |
| | | |
C6A—N1A—C2A—O2A | 178.3 (3) | N3X'—C1X—C2X—O2X | 177.1 (14) |
C6A—N1A—C2A—N3A | −1.4 (5) | N3X'—C1X—C2X—N3X | −1.1 (11) |
O2A—C2A—N3A—C4A | −178.6 (3) | C2X—C1X—N3X'—C2X' | −1.0 (11) |
N1A—C2A—N3A—C4A | 1.1 (5) | C2X—C1X—N3X'—C5X' | 172 (2) |
C2A—N3A—C4A—O4A | 179.5 (3) | C2X—O2X—C2X'—N3X' | 1.6 (8) |
C2A—N3A—C4A—C5A | 0.0 (5) | C2X—O2X—C2X'—C4X | −178 (3) |
O4A—C4A—C5A—C6A | 179.6 (4) | C1X—N3X'—C2X'—O2X | −1 (2) |
N3A—C4A—C5A—C6A | −0.9 (5) | C5X'—N3X'—C2X'—O2X | −173.0 (17) |
C2A—N1A—C6A—N6A | −178.8 (3) | C1X—N3X'—C2X'—C4X | 179.1 (12) |
C2A—N1A—C6A—C5A | 0.5 (5) | C5X'—N3X'—C2X'—C4X | 7 (3) |
C4A—C5A—C6A—N6A | 179.9 (4) | N3X—C4X—C2X'—O2X | 179 (3) |
C4A—C5A—C6A—N1A | 0.7 (5) | N3X—C4X—C2X'—N3X' | −1.0 (9) |
C6B—N1B—C2B—O2B | −179.9 (3) | C2Y'—C4Y—N3Y—C2Y | −1.3 (7) |
C6B—N1B—C2B—N3B | 0.3 (5) | C2Y'—C4Y—N3Y—C5Y | 166.1 (12) |
O2B—C2B—N3B—C4B | −179.7 (3) | C2Y'—O2Y—C2Y—N3Y | 5.4 (8) |
N1B—C2B—N3B—C4B | 0.1 (5) | C2Y'—O2Y—C2Y—C1Y | −178.1 (12) |
C2B—N3B—C4B—O4B | −179.2 (3) | C4Y—N3Y—C2Y—O2Y | −5.4 (8) |
C2B—N3B—C4B—C5B | 0.2 (5) | C5Y—N3Y—C2Y—O2Y | −172.0 (9) |
O4B—C4B—C5B—C6B | 178.5 (4) | C4Y—N3Y—C2Y—C1Y | 177.8 (5) |
N3B—C4B—C5B—C6B | −0.8 (5) | C5Y—N3Y—C2Y—C1Y | 11.2 (11) |
C4B—C5B—C6B—N6B | −177.6 (3) | N3Y'—C1Y—C2Y—O2Y | −179.7 (10) |
C4B—C5B—C6B—N1B | 1.2 (5) | N3Y'—C1Y—C2Y—N3Y | −3.3 (6) |
C2B—N1B—C6B—N6B | 177.9 (3) | C2Y—C1Y—N3Y'—C2Y' | −1.4 (7) |
C2B—N1B—C6B—C5B | −1.0 (5) | C2Y—C1Y—N3Y'—C5Y' | −174.0 (13) |
C2X'—C4X—N3X—C2X | −0.9 (13) | C2Y—O2Y—C2Y'—N3Y' | −0.6 (6) |
C2X'—C4X—N3X—C5X | −175.3 (14) | C2Y—O2Y—C2Y'—C4Y | −174.8 (15) |
C2X'—O2X—C2X—N3X | 0.4 (14) | C5Y'—N3Y'—C2Y'—O2Y | 174.6 (12) |
C2X'—O2X—C2X—C1X | −177.8 (16) | C1Y—N3Y'—C2Y'—O2Y | 2.8 (11) |
C4X—N3X—C2X—O2X | 0.8 (7) | C5Y'—N3Y'—C2Y'—C4Y | −10.3 (16) |
C5X—N3X—C2X—O2X | 174.6 (4) | C1Y—N3Y'—C2Y'—C4Y | 178.0 (6) |
C4X—N3X—C2X—C1X | 179.1 (4) | N3Y—C4Y—C2Y'—O2Y | 170.7 (15) |
C5X—N3X—C2X—C1X | −7.1 (7) | N3Y—C4Y—C2Y'—N3Y' | −3.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O2Y | 0.84 (4) | 1.95 (4) | 2.750 (4) | 160 (3) |
N3A—H3A···O4Bi | 0.86 (2) | 1.91 (2) | 2.770 (3) | 173 (3) |
N6A—H61A···O2Aii | 0.89 (4) | 1.97 (4) | 2.857 (4) | 176 (4) |
N6A—H62A···O2Y | 0.89 (4) | 2.17 (4) | 2.931 (4) | 143 (3) |
N1B—H1B···O2X | 0.86 (4) | 1.93 (4) | 2.746 (4) | 156 (3) |
N3B—H3B···O4A | 0.89 (2) | 1.86 (2) | 2.738 (3) | 173 (3) |
N6B—H61B···O2Bii | 0.87 (4) | 2.07 (4) | 2.902 (4) | 162 (4) |
N6B—H62B···O2X | 0.85 (4) | 2.21 (4) | 2.914 (4) | 140 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
(Ic) 6-Aminouracil 1-methylpyrrolidin-2-one monosolvate
top
Crystal data top
C4H5N3O2·C5H9NO | F(000) = 480 |
Mr = 226.24 | Dx = 1.429 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5460 reflections |
a = 7.5767 (14) Å | θ = 3.4–26.0° |
b = 21.889 (3) Å | µ = 0.11 mm−1 |
c = 7.1356 (11) Å | T = 173 K |
β = 117.312 (12)° | Needle, colourless |
V = 1051.5 (3) Å3 | 0.40 × 0.20 × 0.08 mm |
Z = 4 | |
Data collection top
Stoe IPDS II two-circle diffractometer | 1984 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1503 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.118 |
ω scans | θmax = 25.7°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.958, Tmax = 0.992 | k = −26→25 |
8060 measured reflections | l = −7→8 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0947P)2 + 0.2142P] where P = (Fo2 + 2Fc2)/3 |
1984 reflections | (Δ/σ)max < 0.001 |
212 parameters | Δρmax = 0.28 e Å−3 |
49 restraints | Δρmin = −0.27 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 | Occ. (<1) |
N1 | 0.2004 (3) | 0.57385 (10) | 0.6825 (3) | 0.0296 (5) | |
H1 | 0.233 (4) | 0.5345 (15) | 0.711 (5) | 0.035* | |
C2 | 0.1729 (3) | 0.61193 (11) | 0.8184 (4) | 0.0282 (5) | |
O2 | 0.1797 (3) | 0.59362 (8) | 0.9834 (3) | 0.0356 (5) | |
N3 | 0.1374 (3) | 0.67143 (9) | 0.7561 (3) | 0.0293 (5) | |
H3 | 0.121 (4) | 0.7007 (13) | 0.844 (5) | 0.035* | |
C4 | 0.1308 (3) | 0.69516 (11) | 0.5709 (4) | 0.0296 (6) | |
O4 | 0.1012 (3) | 0.75085 (8) | 0.5418 (3) | 0.0394 (5) | |
C5 | 0.1606 (3) | 0.65354 (11) | 0.4387 (4) | 0.0293 (6) | |
H5 | 0.1569 | 0.6670 | 0.3103 | 0.035* | |
C6 | 0.1954 (3) | 0.59293 (11) | 0.4969 (4) | 0.0288 (5) | |
N6 | 0.2292 (4) | 0.54936 (11) | 0.3849 (4) | 0.0413 (6) | |
H61 | 0.229 (5) | 0.5592 (16) | 0.266 (6) | 0.050* | |
H62 | 0.251 (4) | 0.5082 (16) | 0.439 (6) | 0.050* | |
O2X | 0.3104 (3) | 0.45334 (9) | 0.7012 (3) | 0.0442 (5) | |
C1X | 0.2884 (10) | 0.4410 (3) | 1.0813 (10) | 0.0380 (14) | 0.666 (7) |
H1X1 | 0.2892 | 0.4239 | 1.2087 | 0.057* | 0.666 (7) |
H1X2 | 0.1596 | 0.4603 | 0.9943 | 0.057* | 0.666 (7) |
H1X3 | 0.3942 | 0.4715 | 1.1214 | 0.057* | 0.666 (7) |
C2X | 0.3307 (13) | 0.4029 (3) | 0.7853 (11) | 0.0317 (16) | 0.666 (7) |
C3X | 0.3696 (13) | 0.3427 (4) | 0.7118 (13) | 0.0425 (18) | 0.666 (7) |
H3X1 | 0.5021 | 0.3428 | 0.7163 | 0.051* | 0.666 (7) |
H3X2 | 0.2681 | 0.3345 | 0.5651 | 0.051* | 0.666 (7) |
C4X | 0.3606 (7) | 0.2946 (2) | 0.8577 (8) | 0.0477 (14) | 0.666 (7) |
H4X1 | 0.4847 | 0.2704 | 0.9207 | 0.057* | 0.666 (7) |
H4X2 | 0.2470 | 0.2667 | 0.7813 | 0.057* | 0.666 (7) |
C5X | 0.3343 (14) | 0.3304 (3) | 1.0288 (11) | 0.0343 (17) | 0.666 (7) |
H5X1 | 0.2118 | 0.3176 | 1.0352 | 0.041* | 0.666 (7) |
H5X2 | 0.4495 | 0.3242 | 1.1691 | 0.041* | 0.666 (7) |
N1X | 0.3209 (5) | 0.39293 (17) | 0.9633 (7) | 0.0335 (11) | 0.666 (7) |
C1Y | 0.401 (3) | 0.3352 (9) | 0.664 (3) | 0.046 (4) | 0.334 (7) |
H1Y1 | 0.4320 | 0.2915 | 0.6842 | 0.069* | 0.334 (7) |
H1Y2 | 0.5149 | 0.3575 | 0.6680 | 0.069* | 0.334 (7) |
H1Y3 | 0.2848 | 0.3417 | 0.5270 | 0.069* | 0.334 (7) |
C2Y | 0.313 (3) | 0.4150 (5) | 0.835 (2) | 0.036 (4) | 0.334 (7) |
C3Y | 0.267 (2) | 0.4223 (6) | 1.017 (2) | 0.049 (4) | 0.334 (7) |
H3Y1 | 0.3559 | 0.4530 | 1.1177 | 0.059* | 0.334 (7) |
H3Y2 | 0.1275 | 0.4358 | 0.9663 | 0.059* | 0.334 (7) |
C4Y | 0.2979 (14) | 0.3611 (5) | 1.1198 (17) | 0.054 (3) | 0.334 (7) |
H4Y1 | 0.1802 | 0.3489 | 1.1369 | 0.065* | 0.334 (7) |
H4Y2 | 0.4156 | 0.3616 | 1.2603 | 0.065* | 0.334 (7) |
C5Y | 0.330 (3) | 0.3170 (5) | 0.970 (2) | 0.039 (4) | 0.334 (7) |
H5Y1 | 0.4481 | 0.2909 | 1.0484 | 0.047* | 0.334 (7) |
H5Y2 | 0.2123 | 0.2906 | 0.8936 | 0.047* | 0.334 (7) |
N1Y | 0.3588 (10) | 0.3572 (4) | 0.8291 (14) | 0.039 (2) | 0.334 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0414 (11) | 0.0238 (11) | 0.0272 (11) | 0.0023 (8) | 0.0190 (9) | 0.0027 (9) |
C2 | 0.0328 (12) | 0.0275 (12) | 0.0265 (13) | −0.0018 (9) | 0.0156 (10) | 0.0013 (10) |
O2 | 0.0535 (11) | 0.0341 (10) | 0.0264 (10) | 0.0005 (8) | 0.0246 (8) | 0.0047 (8) |
N3 | 0.0414 (11) | 0.0250 (11) | 0.0279 (11) | 0.0008 (8) | 0.0213 (9) | 0.0003 (9) |
C4 | 0.0351 (12) | 0.0296 (13) | 0.0273 (12) | −0.0010 (9) | 0.0171 (10) | 0.0034 (10) |
O4 | 0.0654 (12) | 0.0248 (9) | 0.0402 (12) | 0.0051 (8) | 0.0347 (10) | 0.0049 (8) |
C5 | 0.0400 (12) | 0.0291 (13) | 0.0239 (13) | −0.0006 (10) | 0.0190 (10) | 0.0023 (10) |
C6 | 0.0360 (12) | 0.0302 (13) | 0.0231 (12) | 0.0004 (9) | 0.0160 (10) | 0.0012 (10) |
N6 | 0.0727 (17) | 0.0300 (13) | 0.0322 (13) | 0.0080 (11) | 0.0336 (12) | 0.0053 (10) |
O2X | 0.0625 (12) | 0.0298 (11) | 0.0478 (12) | 0.0059 (8) | 0.0318 (10) | 0.0093 (9) |
C1X | 0.042 (3) | 0.034 (3) | 0.042 (3) | −0.002 (2) | 0.023 (3) | −0.001 (3) |
C2X | 0.035 (3) | 0.026 (4) | 0.033 (3) | 0.000 (2) | 0.014 (2) | 0.001 (3) |
C3X | 0.045 (3) | 0.037 (4) | 0.044 (5) | 0.001 (3) | 0.019 (3) | −0.008 (3) |
C4X | 0.058 (3) | 0.026 (2) | 0.045 (3) | 0.0019 (18) | 0.012 (2) | −0.005 (2) |
C5X | 0.043 (3) | 0.026 (3) | 0.030 (3) | −0.007 (3) | 0.013 (3) | −0.003 (3) |
N1X | 0.0401 (19) | 0.026 (2) | 0.033 (2) | −0.0017 (14) | 0.0151 (15) | 0.0004 (18) |
C1Y | 0.051 (7) | 0.029 (5) | 0.053 (8) | 0.001 (4) | 0.020 (5) | −0.012 (5) |
C2Y | 0.030 (5) | 0.035 (6) | 0.044 (8) | 0.001 (4) | 0.018 (5) | −0.001 (6) |
C3Y | 0.049 (6) | 0.046 (8) | 0.046 (7) | −0.004 (6) | 0.016 (5) | 0.007 (6) |
C4Y | 0.044 (4) | 0.065 (6) | 0.053 (6) | −0.012 (4) | 0.023 (4) | 0.014 (5) |
C5Y | 0.043 (5) | 0.021 (5) | 0.044 (8) | 0.001 (4) | 0.012 (6) | 0.005 (6) |
N1Y | 0.035 (3) | 0.038 (5) | 0.045 (5) | 0.005 (3) | 0.019 (3) | 0.001 (4) |
Geometric parameters (Å, º) top
N1—C2 | 1.366 (3) | C3X—H3X1 | 0.9900 |
N1—C6 | 1.373 (3) | C3X—H3X2 | 0.9900 |
N1—H1 | 0.89 (3) | C4X—C5X | 1.539 (7) |
C2—O2 | 1.222 (3) | C4X—H4X1 | 0.9900 |
C2—N3 | 1.363 (3) | C4X—H4X2 | 0.9900 |
N3—C4 | 1.399 (3) | C5X—N1X | 1.434 (6) |
N3—H3 | 0.94 (3) | C5X—H5X1 | 0.9900 |
C4—O4 | 1.240 (3) | C5X—H5X2 | 0.9900 |
C4—C5 | 1.403 (3) | C1Y—N1Y | 1.438 (11) |
C5—C6 | 1.379 (3) | C1Y—H1Y1 | 0.9800 |
C5—H5 | 0.9500 | C1Y—H1Y2 | 0.9800 |
C6—N6 | 1.342 (3) | C1Y—H1Y3 | 0.9800 |
N6—H61 | 0.87 (4) | C2Y—N1Y | 1.319 (10) |
N6—H62 | 0.96 (4) | C2Y—C3Y | 1.497 (13) |
O2X—C2X | 1.232 (6) | C3Y—C4Y | 1.493 (13) |
O2X—C2Y | 1.266 (12) | C3Y—H3Y1 | 0.9900 |
C1X—N1X | 1.438 (7) | C3Y—H3Y2 | 0.9900 |
C1X—H1X1 | 0.9800 | C4Y—C5Y | 1.539 (12) |
C1X—H1X2 | 0.9800 | C4Y—H4Y1 | 0.9900 |
C1X—H1X3 | 0.9800 | C4Y—H4Y2 | 0.9900 |
C2X—N1X | 1.324 (7) | C5Y—N1Y | 1.427 (11) |
C2X—C3X | 1.496 (9) | C5Y—H5Y1 | 0.9900 |
C3X—C4X | 1.503 (10) | C5Y—H5Y2 | 0.9900 |
| | | |
C2—N1—C6 | 123.7 (2) | H4X1—C4X—H4X2 | 108.8 |
C2—N1—H1 | 123 (2) | N1X—C5X—C4X | 104.0 (4) |
C6—N1—H1 | 113 (2) | N1X—C5X—H5X1 | 111.0 |
O2—C2—N3 | 122.9 (2) | C4X—C5X—H5X1 | 111.0 |
O2—C2—N1 | 122.1 (2) | N1X—C5X—H5X2 | 111.0 |
N3—C2—N1 | 115.0 (2) | C4X—C5X—H5X2 | 111.0 |
C2—N3—C4 | 125.4 (2) | H5X1—C5X—H5X2 | 109.0 |
C2—N3—H3 | 120.0 (18) | C2X—N1X—C5X | 116.3 (5) |
C4—N3—H3 | 114.5 (18) | C2X—N1X—C1X | 122.8 (5) |
O4—C4—N3 | 116.7 (2) | C5X—N1X—C1X | 120.8 (5) |
O4—C4—C5 | 126.8 (2) | N1Y—C1Y—H1Y1 | 109.5 |
N3—C4—C5 | 116.6 (2) | N1Y—C1Y—H1Y2 | 109.5 |
C6—C5—C4 | 119.3 (2) | H1Y1—C1Y—H1Y2 | 109.5 |
C6—C5—H5 | 120.3 | N1Y—C1Y—H1Y3 | 109.5 |
C4—C5—H5 | 120.3 | H1Y1—C1Y—H1Y3 | 109.5 |
N6—C6—N1 | 115.5 (2) | H1Y2—C1Y—H1Y3 | 109.5 |
N6—C6—C5 | 124.5 (2) | O2X—C2Y—N1Y | 121.5 (10) |
N1—C6—C5 | 120.0 (2) | O2X—C2Y—C3Y | 131.0 (9) |
C6—N6—H61 | 119 (2) | N1Y—C2Y—C3Y | 107.5 (10) |
C6—N6—H62 | 118 (2) | C4Y—C3Y—C2Y | 106.5 (10) |
H61—N6—H62 | 123 (3) | C4Y—C3Y—H3Y1 | 110.4 |
N1X—C1X—H1X1 | 109.5 | C2Y—C3Y—H3Y1 | 110.4 |
N1X—C1X—H1X2 | 109.5 | C4Y—C3Y—H3Y2 | 110.4 |
H1X1—C1X—H1X2 | 109.5 | C2Y—C3Y—H3Y2 | 110.4 |
N1X—C1X—H1X3 | 109.5 | H3Y1—C3Y—H3Y2 | 108.6 |
H1X1—C1X—H1X3 | 109.5 | C3Y—C4Y—C5Y | 105.1 (8) |
H1X2—C1X—H1X3 | 109.5 | C3Y—C4Y—H4Y1 | 110.7 |
O2X—C2X—N1X | 124.4 (6) | C5Y—C4Y—H4Y1 | 110.7 |
O2X—C2X—C3X | 128.3 (6) | C3Y—C4Y—H4Y2 | 110.7 |
N1X—C2X—C3X | 107.3 (5) | C5Y—C4Y—H4Y2 | 110.7 |
C2X—C3X—C4X | 107.2 (6) | H4Y1—C4Y—H4Y2 | 108.8 |
C2X—C3X—H3X1 | 110.3 | N1Y—C5Y—C4Y | 103.1 (8) |
C4X—C3X—H3X1 | 110.3 | N1Y—C5Y—H5Y1 | 111.1 |
C2X—C3X—H3X2 | 110.3 | C4Y—C5Y—H5Y1 | 111.1 |
C4X—C3X—H3X2 | 110.3 | N1Y—C5Y—H5Y2 | 111.1 |
H3X1—C3X—H3X2 | 108.5 | C4Y—C5Y—H5Y2 | 111.1 |
C3X—C4X—C5X | 104.9 (5) | H5Y1—C5Y—H5Y2 | 109.1 |
C3X—C4X—H4X1 | 110.8 | C2Y—N1Y—C5Y | 116.0 (9) |
C5X—C4X—H4X1 | 110.8 | C2Y—N1Y—C1Y | 120.6 (11) |
C3X—C4X—H4X2 | 110.8 | C5Y—N1Y—C1Y | 122.4 (12) |
C5X—C4X—H4X2 | 110.8 | | |
| | | |
C6—N1—C2—O2 | −179.4 (2) | O2X—C2X—N1X—C5X | 175.7 (7) |
C6—N1—C2—N3 | 0.7 (3) | C3X—C2X—N1X—C5X | −4.2 (9) |
O2—C2—N3—C4 | 179.0 (2) | O2X—C2X—N1X—C1X | −1.2 (11) |
N1—C2—N3—C4 | −1.1 (3) | C3X—C2X—N1X—C1X | 178.9 (5) |
C2—N3—C4—O4 | −178.3 (2) | C4X—C5X—N1X—C2X | 0.9 (8) |
C2—N3—C4—C5 | 1.0 (3) | C4X—C5X—N1X—C1X | 177.9 (5) |
O4—C4—C5—C6 | 178.8 (2) | C2X—O2X—C2Y—N1Y | 1.1 (15) |
N3—C4—C5—C6 | −0.4 (3) | C2X—O2X—C2Y—C3Y | −178 (5) |
C2—N1—C6—N6 | 178.8 (2) | O2X—C2Y—C3Y—C4Y | −179.3 (16) |
C2—N1—C6—C5 | −0.2 (3) | N1Y—C2Y—C3Y—C4Y | 1.6 (17) |
C4—C5—C6—N6 | −178.9 (2) | C2Y—C3Y—C4Y—C5Y | −8.9 (16) |
C4—C5—C6—N1 | 0.1 (3) | C3Y—C4Y—C5Y—N1Y | 12.5 (15) |
C2Y—O2X—C2X—N1X | −5 (2) | O2X—C2Y—N1Y—C5Y | −171.8 (14) |
C2Y—O2X—C2X—C3X | 175 (4) | C3Y—C2Y—N1Y—C5Y | 7.5 (18) |
O2X—C2X—C3X—C4X | −174.2 (7) | O2X—C2Y—N1Y—C1Y | −2 (2) |
N1X—C2X—C3X—C4X | 5.7 (8) | C3Y—C2Y—N1Y—C1Y | 176.9 (13) |
C2X—C3X—C4X—C5X | −5.0 (8) | C4Y—C5Y—N1Y—C2Y | −12.9 (17) |
C3X—C4X—C5X—N1X | 2.7 (7) | C4Y—C5Y—N1Y—C1Y | 178.0 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2X | 0.89 (3) | 1.88 (3) | 2.751 (3) | 164 (3) |
N3—H3···O4i | 0.94 (3) | 1.83 (3) | 2.764 (3) | 172 (3) |
N6—H61···O2ii | 0.87 (4) | 2.02 (4) | 2.881 (3) | 168 (3) |
N6—H62···O2X | 0.96 (4) | 2.09 (4) | 2.936 (3) | 145 (3) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z−1. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.