Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011204930X/fg3285sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011204930X/fg3285Iasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011204930X/fg3285Ibsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011204930X/fg3285Icsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011204930X/fg3285Idsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011204930X/fg3285Iesup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010827011204930X/fg3285sup7.pdf |
CCDC references: 925273; 925274; 925275; 925276; 925277
Solvent evaporation experiments with the commercially available monohydrate of 6-amino-2-thiouracil under different conditions yielded compounds (Ia)–(Ie) (Table 6).
All H atoms except those of the disordered solvent molecules were initially located by difference Fourier syntheses. Subsequently, all H atoms in (Ia) and (Id), the H atoms bonded to C atoms in (Ib), (Ic) and (Ie), and the H atoms of the imide groups in (Ic) and (Ie) were refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å, aromatic C—H = 0.95 Å and N—H = 0.88 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) for secondary and aromatic H atoms, and Uiso(H) = 1.2Ueq(N). In (Ib), all H atoms bonded to N atoms were refined isotropically and the N—H bond lengths were restrained to 0.88 (2) Å. In (Ic) and (Ie), the isotropic refinement of the H atoms of the amino groups resulted in isotropic displacement parameters being smaller than the equivalent isotropic displacement parameters of the parent N atoms. Therefore, they were coupled to those of the N atoms with Uiso(H) = 1.2Ueq(N) and the N—H distances were restrained to 0.88 (2) Å. For all methyl groups except those of the disordered solvent molecules, free rotation about their local threefold axis was allowed.
The DMAC molecule in (Ib) and the DMAC molecules X and Y in (Ic), respectively, show disorder over a pseudo-mirror plane along atoms O21(X/Y) and C32(X/Y) [site-occupation factor for the major occupied orientation = 0.629 (8) in (Ib), and 0.712 (11) for X and 0.630 (11) for Y in (Ic)].
In (Id), NMP molecules Y and Z show disorder over a pseudo-mirror plane, respectively [site-occupation factor for the major occupied orientation = 0.600 (14) for Y and 0.688 (11) for Z]. In molecule Y, the pseudo-mirror plane intersects the bonds N1Y—C2Y and C4Y—C5Y; thus all atom positions are different for both orientations. In molecule Z, the pseudo-mirror plane intersects O21Z and the bonds N1Y—C2Y and C4Y—C5Y; hence, the positions of O21Z coincide in both orientations.
Similarity restraints for the 1,2 and 1,3 distances were applied for all solvent molecules in (Ib), (Id) and (Ie) and for solvent molecules X and Y in (Ic).
The isotropic restraint (ISOR), similar-ADP restraint (SIMU) and rigid-bond restraint (DELU) were applied for all solvent molecules in (Ie) and for the disordered DMAC molecules X and Y in (Ic). In (Id), SIMU and DELU were applied for the disordered NMP molecules Y and Z.
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); molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
A perspective view of (Ia), showing the atom-numbering scheme.
Displacement ellipsoids are drawn at the 50% probability level and H atoms are
shown as small spheres of arbitrary radii. The dashed lines indicate N—H···O
hydrogen bonds. A partial packing diagram for (Ia) with chains of (I) running parallel [110]. N—H···O hydrogen bonds are shown as dashed lines. [Symmetry code: (i) x -1, y+1, z.] A perspective view of (Ib), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate N—H···O hydrogen bonds. Only the major occupied site of the disordered dimethylacetamide molecule is shown. A partial packing diagram for (Ib). N—H···O hydrogen bonds are shown as dashed lines. Only the major occupied site of the disordered dimethylacetamide molecules is shown. [Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1/2, y+1/2, -z+1/2.] A perspective view of (Ic), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate N—H···O hydrogen bonds. Dimethylacetamide molecules X and Y are disordered and only the major occupied sites are shown. A perspective view of (Id), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate N—H···O hydrogen bonds. Only the major occupied sites of the disordered NMP molecules Y and Z are shown. A partial packing diagram for (Ic). N—H···O hydrogen bonds are shown as dashed lines. Dimethylacetamide molecule Y is not displayed. Only the major occupied site of the disordered DMAC molecule X is shown. [Symmetry code: (i) x+1/2, -y+1, z.] A view of the packing of the isomorphous compound (Id) is with the Supplementary materials. A perspective view of (Ie), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate N—H···O hydrogen bonds. A partial packing diagram for (Ie). N—H···O hydrogen bonds are shown as dashed lines. The N-methyl-2-pyrrolidone molecule Y is not displayed. [Symmetry code: (i) -x+1/2, y-1/2, z.] Packing diagram for (Ie). N—H···O hydrogen bonds are shown as dashed lines. |
C4H5N3OS·2C3H7NO | Z = 4 |
Mr = 289.36 | F(000) = 616 |
Triclinic, P1 | Dx = 1.318 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0894 (16) Å | Cell parameters from 3717 reflections |
b = 12.037 (3) Å | θ = 3.4–25.6° |
c = 15.390 (3) Å | µ = 0.23 mm−1 |
α = 89.774 (19)° | T = 173 K |
β = 89.466 (17)° | Needle, colourless |
γ = 76.691 (17)° | 0.30 × 0.15 × 0.10 mm |
V = 1458.2 (5) Å3 |
Stoe IPDS II two-circle diffractometer | 5428 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1966 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.105 |
ω scans | θmax = 25.7°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.933, Tmax = 0.977 | k = −14→14 |
11063 measured reflections | l = −18→17 |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0408P)2] where P = (Fo2 + 2Fc2)/3 |
5428 reflections | (Δ/σ)max < 0.001 |
351 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C4H5N3OS·2C3H7NO | γ = 76.691 (17)° |
Mr = 289.36 | V = 1458.2 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.0894 (16) Å | Mo Kα radiation |
b = 12.037 (3) Å | µ = 0.23 mm−1 |
c = 15.390 (3) Å | T = 173 K |
α = 89.774 (19)° | 0.30 × 0.15 × 0.10 mm |
β = 89.466 (17)° |
Stoe IPDS II two-circle diffractometer | 5428 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1966 reflections with I > 2σ(I) |
Tmin = 0.933, Tmax = 0.977 | Rint = 0.105 |
11063 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.21 e Å−3 |
5428 reflections | Δρmin = −0.40 e Å−3 |
351 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.6207 (8) | 0.3706 (5) | 0.2390 (4) | 0.0619 (15) | |
H1A | 0.5576 | 0.4406 | 0.2428 | 0.074* | |
C2A | 0.6119 (10) | 0.3098 (6) | 0.1637 (5) | 0.067 (2) | |
S21A | 0.4830 (3) | 0.36552 (18) | 0.08513 (14) | 0.0722 (6) | |
N3A | 0.7130 (8) | 0.2038 (5) | 0.1634 (4) | 0.0632 (16) | |
H3A | 0.7152 | 0.1637 | 0.1155 | 0.076* | |
C4A | 0.8130 (10) | 0.1521 (6) | 0.2306 (5) | 0.067 (2) | |
O41A | 0.8954 (7) | 0.0520 (4) | 0.2175 (3) | 0.0719 (15) | |
C5A | 0.8172 (10) | 0.2165 (6) | 0.3059 (5) | 0.0629 (18) | |
H5A | 0.8837 | 0.1841 | 0.3542 | 0.076* | |
C6A | 0.7233 (9) | 0.3275 (6) | 0.3088 (5) | 0.0615 (17) | |
N61A | 0.7177 (8) | 0.4003 (5) | 0.3751 (4) | 0.0713 (18) | |
H61A | 0.7777 | 0.3784 | 0.4221 | 0.086* | |
H61B | 0.6540 | 0.4701 | 0.3716 | 0.086* | |
N1B | 0.1386 (8) | 0.8772 (5) | 0.2615 (4) | 0.0640 (16) | |
H1B | 0.0654 | 0.9436 | 0.2583 | 0.077* | |
C2B | 0.2364 (10) | 0.8545 (6) | 0.3330 (4) | 0.0636 (18) | |
S21B | 0.2231 (3) | 0.95078 (18) | 0.41132 (14) | 0.0740 (6) | |
N3B | 0.3436 (8) | 0.7511 (5) | 0.3356 (4) | 0.0649 (16) | |
H3B | 0.4027 | 0.7320 | 0.3833 | 0.078* | |
C4B | 0.3679 (9) | 0.6714 (6) | 0.2679 (5) | 0.0619 (18) | |
O41B | 0.4763 (7) | 0.5793 (4) | 0.2823 (4) | 0.0737 (15) | |
C5B | 0.2648 (10) | 0.6986 (6) | 0.1953 (5) | 0.0639 (19) | |
H5B | 0.2760 | 0.6467 | 0.1481 | 0.077* | |
C6B | 0.1471 (11) | 0.8008 (6) | 0.1921 (5) | 0.0675 (19) | |
N61B | 0.0401 (8) | 0.8374 (5) | 0.1262 (4) | 0.0693 (18) | |
H61C | 0.0419 | 0.7943 | 0.0799 | 0.083* | |
H61D | −0.0319 | 0.9043 | 0.1293 | 0.083* | |
C1W | 1.0400 (11) | 0.2311 (7) | 0.5340 (5) | 0.071 (2) | |
H1W | 1.0448 | 0.1682 | 0.4962 | 0.085* | |
O11W | 0.9387 (8) | 0.3215 (5) | 0.5153 (4) | 0.0842 (17) | |
N2W | 1.1423 (9) | 0.2137 (5) | 0.6018 (4) | 0.0685 (17) | |
C3W | 1.1433 (11) | 0.3082 (7) | 0.6621 (5) | 0.077 (2) | |
H3W1 | 1.2550 | 0.3267 | 0.6603 | 0.116* | |
H3W2 | 1.1193 | 0.2854 | 0.7212 | 0.116* | |
H3W3 | 1.0561 | 0.3754 | 0.6449 | 0.116* | |
C4W | 1.2571 (12) | 0.1054 (7) | 0.6196 (5) | 0.083 (3) | |
H4W1 | 1.2453 | 0.0502 | 0.5748 | 0.125* | |
H4W2 | 1.2298 | 0.0774 | 0.6767 | 0.125* | |
H4W3 | 1.3742 | 0.1150 | 0.6196 | 0.125* | |
C1X | 0.6257 (12) | 0.0847 (7) | −0.0346 (6) | 0.078 (2) | |
H1X | 0.5481 | 0.1571 | −0.0317 | 0.093* | |
O11X | 0.7257 (8) | 0.0565 (5) | 0.0255 (4) | 0.0790 (16) | |
N2X | 0.6202 (9) | 0.0182 (5) | −0.1047 (4) | 0.0724 (18) | |
C3X | 0.7311 (14) | −0.0945 (8) | −0.1101 (6) | 0.091 (3) | |
H3X1 | 0.8148 | −0.1041 | −0.0634 | 0.137* | |
H3X2 | 0.7900 | −0.1035 | −0.1664 | 0.137* | |
H3X3 | 0.6637 | −0.1521 | −0.1040 | 0.137* | |
C4X | 0.4977 (13) | 0.0559 (9) | −0.1725 (6) | 0.092 (3) | |
H4X1 | 0.4377 | 0.1351 | −0.1617 | 0.138* | |
H4X2 | 0.4158 | 0.0072 | −0.1730 | 0.138* | |
H4X3 | 0.5564 | 0.0508 | −0.2289 | 0.138* | |
C1Y | 0.5633 (12) | 0.7282 (8) | 0.5370 (6) | 0.080 (2) | |
H1Y | 0.4968 | 0.8043 | 0.5391 | 0.096* | |
O11Y | 0.5486 (8) | 0.6677 (5) | 0.4728 (4) | 0.0881 (19) | |
N2Y | 0.6683 (9) | 0.6904 (6) | 0.6026 (4) | 0.0738 (18) | |
C3Y | 0.7693 (12) | 0.5757 (7) | 0.6038 (6) | 0.086 (3) | |
H3Y1 | 0.7319 | 0.5316 | 0.5576 | 0.128* | |
H3Y2 | 0.7561 | 0.5406 | 0.6602 | 0.128* | |
H3Y3 | 0.8890 | 0.5766 | 0.5943 | 0.128* | |
C4Y | 0.6885 (14) | 0.7645 (8) | 0.6737 (6) | 0.091 (3) | |
H4Y1 | 0.6174 | 0.8411 | 0.6637 | 0.137* | |
H4Y2 | 0.8078 | 0.7688 | 0.6772 | 0.137* | |
H4Y3 | 0.6541 | 0.7339 | 0.7283 | 0.137* | |
C1Z | 0.1333 (11) | 0.5901 (7) | −0.0315 (5) | 0.069 (2) | |
H1Z | 0.2239 | 0.5594 | 0.0067 | 0.083* | |
O11Z | 0.0410 (8) | 0.6853 (5) | −0.0145 (4) | 0.0794 (16) | |
N2Z | 0.1114 (8) | 0.5285 (5) | −0.1012 (4) | 0.0656 (16) | |
C3Z | −0.0206 (12) | 0.5717 (8) | −0.1636 (5) | 0.081 (2) | |
H3Z1 | −0.0889 | 0.6454 | −0.1437 | 0.122* | |
H3Z2 | −0.0935 | 0.5174 | −0.1693 | 0.122* | |
H3Z3 | 0.0312 | 0.5814 | −0.2201 | 0.122* | |
C4Z | 0.2233 (12) | 0.4162 (7) | −0.1166 (5) | 0.077 (2) | |
H4Z1 | 0.3169 | 0.4032 | −0.0751 | 0.116* | |
H4Z2 | 0.2692 | 0.4129 | −0.1759 | 0.116* | |
H4Z3 | 0.1587 | 0.3571 | −0.1091 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.056 (4) | 0.060 (3) | 0.065 (3) | −0.004 (3) | −0.008 (3) | 0.000 (2) |
C2A | 0.065 (5) | 0.080 (4) | 0.054 (3) | −0.011 (4) | 0.002 (3) | 0.000 (3) |
S21A | 0.0642 (12) | 0.0743 (10) | 0.0750 (11) | −0.0094 (9) | −0.0123 (10) | 0.0019 (8) |
N3A | 0.053 (4) | 0.070 (3) | 0.063 (3) | −0.005 (3) | −0.010 (3) | 0.002 (3) |
C4A | 0.059 (5) | 0.065 (4) | 0.071 (4) | −0.003 (3) | −0.006 (4) | −0.006 (3) |
O41A | 0.073 (4) | 0.065 (3) | 0.069 (3) | 0.002 (3) | −0.007 (3) | 0.000 (2) |
C5A | 0.061 (4) | 0.058 (3) | 0.066 (4) | −0.008 (3) | −0.003 (3) | −0.003 (3) |
C6A | 0.049 (4) | 0.071 (4) | 0.064 (4) | −0.013 (3) | −0.006 (3) | −0.004 (3) |
N61A | 0.067 (4) | 0.077 (3) | 0.066 (3) | −0.009 (3) | −0.010 (3) | −0.010 (3) |
N1B | 0.059 (4) | 0.064 (3) | 0.065 (3) | −0.004 (3) | −0.001 (3) | −0.011 (2) |
C2B | 0.061 (4) | 0.074 (4) | 0.056 (3) | −0.013 (3) | 0.001 (3) | −0.002 (3) |
S21B | 0.0723 (13) | 0.0719 (10) | 0.0749 (12) | −0.0104 (10) | −0.0014 (10) | −0.0105 (9) |
N3B | 0.056 (4) | 0.065 (3) | 0.067 (3) | −0.001 (3) | −0.002 (3) | −0.003 (3) |
C4B | 0.049 (4) | 0.059 (4) | 0.075 (4) | −0.008 (3) | 0.009 (3) | −0.008 (3) |
O41B | 0.068 (3) | 0.069 (3) | 0.076 (3) | 0.001 (3) | 0.000 (3) | −0.008 (2) |
C5B | 0.059 (4) | 0.065 (4) | 0.064 (4) | −0.005 (3) | 0.000 (3) | −0.004 (3) |
C6B | 0.065 (5) | 0.067 (4) | 0.071 (4) | −0.017 (3) | 0.002 (4) | −0.008 (3) |
N61B | 0.062 (4) | 0.071 (3) | 0.070 (3) | −0.007 (3) | −0.010 (3) | −0.008 (3) |
C1W | 0.057 (4) | 0.087 (5) | 0.067 (4) | −0.012 (4) | −0.010 (4) | 0.001 (4) |
O11W | 0.070 (4) | 0.090 (4) | 0.092 (4) | −0.016 (3) | −0.011 (3) | 0.002 (3) |
N2W | 0.065 (4) | 0.070 (3) | 0.072 (4) | −0.017 (3) | −0.009 (3) | −0.004 (3) |
C3W | 0.077 (5) | 0.092 (5) | 0.076 (5) | −0.047 (5) | 0.005 (4) | −0.014 (4) |
C4W | 0.083 (6) | 0.093 (5) | 0.069 (4) | −0.010 (5) | −0.011 (4) | 0.011 (4) |
C1X | 0.077 (6) | 0.075 (4) | 0.081 (5) | −0.018 (4) | 0.009 (5) | −0.009 (4) |
O11X | 0.074 (4) | 0.090 (3) | 0.075 (3) | −0.023 (3) | −0.005 (3) | −0.005 (3) |
N2X | 0.073 (5) | 0.081 (4) | 0.065 (3) | −0.022 (3) | −0.002 (3) | 0.000 (3) |
C3X | 0.104 (8) | 0.085 (5) | 0.085 (6) | −0.023 (5) | 0.009 (5) | −0.011 (4) |
C4X | 0.078 (6) | 0.122 (7) | 0.086 (6) | −0.041 (6) | −0.016 (5) | 0.009 (5) |
C1Y | 0.072 (6) | 0.085 (5) | 0.080 (5) | −0.010 (4) | 0.000 (4) | 0.005 (4) |
O11Y | 0.090 (5) | 0.094 (4) | 0.078 (4) | −0.016 (3) | −0.005 (3) | −0.005 (3) |
N2Y | 0.074 (5) | 0.082 (4) | 0.067 (4) | −0.020 (3) | −0.004 (3) | −0.002 (3) |
C3Y | 0.074 (6) | 0.088 (5) | 0.085 (5) | 0.002 (5) | −0.006 (5) | 0.008 (4) |
C4Y | 0.097 (7) | 0.106 (6) | 0.081 (6) | −0.042 (6) | −0.011 (5) | −0.013 (5) |
C1Z | 0.063 (5) | 0.084 (4) | 0.062 (4) | −0.021 (4) | 0.004 (4) | −0.015 (3) |
O11Z | 0.073 (4) | 0.081 (3) | 0.082 (3) | −0.013 (3) | 0.005 (3) | −0.012 (3) |
N2Z | 0.060 (4) | 0.076 (3) | 0.061 (3) | −0.016 (3) | −0.004 (3) | −0.008 (3) |
C3Z | 0.075 (6) | 0.108 (6) | 0.067 (5) | −0.034 (5) | 0.002 (4) | 0.006 (4) |
C4Z | 0.081 (6) | 0.077 (5) | 0.070 (4) | −0.012 (4) | 0.008 (4) | −0.010 (4) |
N1A—C2A | 1.384 (8) | C4W—H4W1 | 0.9800 |
N1A—C6A | 1.389 (9) | C4W—H4W2 | 0.9800 |
N1A—H1A | 0.8800 | C4W—H4W3 | 0.9800 |
C2A—N3A | 1.348 (8) | C1X—O11X | 1.229 (10) |
C2A—S21A | 1.641 (7) | C1X—N2X | 1.353 (9) |
N3A—C4A | 1.374 (8) | C1X—H1X | 0.9500 |
N3A—H3A | 0.8800 | N2X—C4X | 1.444 (10) |
C4A—O41A | 1.252 (7) | N2X—C3X | 1.446 (10) |
C4A—C5A | 1.402 (9) | C3X—H3X1 | 0.9800 |
C5A—C6A | 1.377 (9) | C3X—H3X2 | 0.9800 |
C5A—H5A | 0.9500 | C3X—H3X3 | 0.9800 |
C6A—N61A | 1.341 (8) | C4X—H4X1 | 0.9800 |
N61A—H61A | 0.8800 | C4X—H4X2 | 0.9800 |
N61A—H61B | 0.8800 | C4X—H4X3 | 0.9800 |
N1B—C2B | 1.351 (9) | C1Y—O11Y | 1.252 (10) |
N1B—C6B | 1.403 (8) | C1Y—N2Y | 1.335 (10) |
N1B—H1B | 0.8800 | C1Y—H1Y | 0.9500 |
C2B—N3B | 1.344 (8) | N2Y—C3Y | 1.433 (9) |
C2B—S21B | 1.661 (7) | N2Y—C4Y | 1.448 (9) |
N3B—C4B | 1.400 (8) | C3Y—H3Y1 | 0.9800 |
N3B—H3B | 0.8800 | C3Y—H3Y2 | 0.9800 |
C4B—O41B | 1.266 (8) | C3Y—H3Y3 | 0.9800 |
C4B—C5B | 1.394 (10) | C4Y—H4Y1 | 0.9800 |
C5B—C6B | 1.372 (9) | C4Y—H4Y2 | 0.9800 |
C5B—H5B | 0.9500 | C4Y—H4Y3 | 0.9800 |
C6B—N61B | 1.346 (9) | C1Z—O11Z | 1.242 (8) |
N61B—H61C | 0.8800 | C1Z—N2Z | 1.343 (8) |
N61B—H61D | 0.8800 | C1Z—H1Z | 0.9500 |
C1W—O11W | 1.237 (9) | N2Z—C3Z | 1.445 (10) |
C1W—N2W | 1.323 (9) | N2Z—C4Z | 1.463 (9) |
C1W—H1W | 0.9500 | C3Z—H3Z1 | 0.9800 |
N2W—C4W | 1.443 (9) | C3Z—H3Z2 | 0.9800 |
N2W—C3W | 1.472 (8) | C3Z—H3Z3 | 0.9800 |
C3W—H3W1 | 0.9800 | C4Z—H4Z1 | 0.9800 |
C3W—H3W2 | 0.9800 | C4Z—H4Z2 | 0.9800 |
C3W—H3W3 | 0.9800 | C4Z—H4Z3 | 0.9800 |
C2A—N1A—C6A | 123.7 (6) | N2W—C4W—H4W3 | 109.5 |
C2A—N1A—H1A | 118.2 | H4W1—C4W—H4W3 | 109.5 |
C6A—N1A—H1A | 118.2 | H4W2—C4W—H4W3 | 109.5 |
N3A—C2A—N1A | 114.1 (6) | O11X—C1X—N2X | 123.5 (8) |
N3A—C2A—S21A | 125.2 (5) | O11X—C1X—H1X | 118.2 |
N1A—C2A—S21A | 120.7 (5) | N2X—C1X—H1X | 118.2 |
C4A—N3A—C2A | 126.4 (6) | C1X—N2X—C4X | 120.7 (8) |
C4A—N3A—H3A | 116.8 | C1X—N2X—C3X | 120.1 (7) |
C2A—N3A—H3A | 116.8 | C4X—N2X—C3X | 119.2 (7) |
O41A—C4A—N3A | 116.3 (6) | N2X—C3X—H3X1 | 109.5 |
O41A—C4A—C5A | 126.1 (7) | N2X—C3X—H3X2 | 109.5 |
N3A—C4A—C5A | 117.6 (6) | H3X1—C3X—H3X2 | 109.5 |
C6A—C5A—C4A | 119.0 (7) | N2X—C3X—H3X3 | 109.5 |
C6A—C5A—H5A | 120.5 | H3X1—C3X—H3X3 | 109.5 |
C4A—C5A—H5A | 120.5 | H3X2—C3X—H3X3 | 109.5 |
N61A—C6A—C5A | 125.9 (6) | N2X—C4X—H4X1 | 109.5 |
N61A—C6A—N1A | 115.0 (6) | N2X—C4X—H4X2 | 109.5 |
C5A—C6A—N1A | 119.1 (6) | H4X1—C4X—H4X2 | 109.5 |
C6A—N61A—H61A | 120.0 | N2X—C4X—H4X3 | 109.5 |
C6A—N61A—H61B | 120.0 | H4X1—C4X—H4X3 | 109.5 |
H61A—N61A—H61B | 120.0 | H4X2—C4X—H4X3 | 109.5 |
C2B—N1B—C6B | 123.7 (6) | O11Y—C1Y—N2Y | 122.9 (8) |
C2B—N1B—H1B | 118.2 | O11Y—C1Y—H1Y | 118.6 |
C6B—N1B—H1B | 118.2 | N2Y—C1Y—H1Y | 118.6 |
N1B—C2B—N3B | 115.9 (6) | C1Y—N2Y—C3Y | 121.0 (7) |
N1B—C2B—S21B | 120.9 (5) | C1Y—N2Y—C4Y | 121.4 (8) |
N3B—C2B—S21B | 123.2 (5) | C3Y—N2Y—C4Y | 117.5 (7) |
C2B—N3B—C4B | 124.7 (6) | N2Y—C3Y—H3Y1 | 109.5 |
C2B—N3B—H3B | 117.6 | N2Y—C3Y—H3Y2 | 109.5 |
C4B—N3B—H3B | 117.6 | H3Y1—C3Y—H3Y2 | 109.5 |
O41B—C4B—C5B | 127.3 (6) | N2Y—C3Y—H3Y3 | 109.5 |
O41B—C4B—N3B | 115.3 (6) | H3Y1—C3Y—H3Y3 | 109.5 |
C5B—C4B—N3B | 117.3 (6) | H3Y2—C3Y—H3Y3 | 109.5 |
C6B—C5B—C4B | 119.7 (6) | N2Y—C4Y—H4Y1 | 109.5 |
C6B—C5B—H5B | 120.1 | N2Y—C4Y—H4Y2 | 109.5 |
C4B—C5B—H5B | 120.1 | H4Y1—C4Y—H4Y2 | 109.5 |
N61B—C6B—C5B | 125.7 (6) | N2Y—C4Y—H4Y3 | 109.5 |
N61B—C6B—N1B | 115.7 (6) | H4Y1—C4Y—H4Y3 | 109.5 |
C5B—C6B—N1B | 118.5 (7) | H4Y2—C4Y—H4Y3 | 109.5 |
C6B—N61B—H61C | 120.0 | O11Z—C1Z—N2Z | 123.3 (8) |
C6B—N61B—H61D | 120.0 | O11Z—C1Z—H1Z | 118.4 |
H61C—N61B—H61D | 120.0 | N2Z—C1Z—H1Z | 118.4 |
O11W—C1W—N2W | 126.1 (8) | C1Z—N2Z—C3Z | 121.3 (7) |
O11W—C1W—H1W | 116.9 | C1Z—N2Z—C4Z | 120.4 (6) |
N2W—C1W—H1W | 116.9 | C3Z—N2Z—C4Z | 118.3 (6) |
C1W—N2W—C4W | 123.0 (6) | N2Z—C3Z—H3Z1 | 109.5 |
C1W—N2W—C3W | 119.6 (7) | N2Z—C3Z—H3Z2 | 109.5 |
C4W—N2W—C3W | 117.3 (7) | H3Z1—C3Z—H3Z2 | 109.5 |
N2W—C3W—H3W1 | 109.5 | N2Z—C3Z—H3Z3 | 109.5 |
N2W—C3W—H3W2 | 109.5 | H3Z1—C3Z—H3Z3 | 109.5 |
H3W1—C3W—H3W2 | 109.5 | H3Z2—C3Z—H3Z3 | 109.5 |
N2W—C3W—H3W3 | 109.5 | N2Z—C4Z—H4Z1 | 109.5 |
H3W1—C3W—H3W3 | 109.5 | N2Z—C4Z—H4Z2 | 109.5 |
H3W2—C3W—H3W3 | 109.5 | H4Z1—C4Z—H4Z2 | 109.5 |
N2W—C4W—H4W1 | 109.5 | N2Z—C4Z—H4Z3 | 109.5 |
N2W—C4W—H4W2 | 109.5 | H4Z1—C4Z—H4Z3 | 109.5 |
H4W1—C4W—H4W2 | 109.5 | H4Z2—C4Z—H4Z3 | 109.5 |
C6A—N1A—C2A—N3A | −0.2 (12) | C2B—N3B—C4B—O41B | 179.0 (8) |
C6A—N1A—C2A—S21A | 178.1 (7) | C2B—N3B—C4B—C5B | −4.6 (12) |
N1A—C2A—N3A—C4A | 3.2 (12) | O41B—C4B—C5B—C6B | 176.6 (9) |
S21A—C2A—N3A—C4A | −175.1 (8) | N3B—C4B—C5B—C6B | 0.8 (12) |
C2A—N3A—C4A—O41A | 178.8 (8) | C4B—C5B—C6B—N61B | −179.9 (9) |
C2A—N3A—C4A—C5A | −2.9 (13) | C4B—C5B—C6B—N1B | 2.4 (12) |
O41A—C4A—C5A—C6A | 177.6 (9) | C2B—N1B—C6B—N61B | 179.9 (8) |
N3A—C4A—C5A—C6A | −0.5 (12) | C2B—N1B—C6B—C5B | −2.2 (13) |
C4A—C5A—C6A—N61A | −178.2 (9) | O11W—C1W—N2W—C4W | 179.8 (9) |
C4A—C5A—C6A—N1A | 3.2 (12) | O11W—C1W—N2W—C3W | −1.1 (14) |
C2A—N1A—C6A—N61A | 178.4 (8) | O11X—C1X—N2X—C4X | 179.0 (10) |
C2A—N1A—C6A—C5A | −2.9 (13) | O11X—C1X—N2X—C3X | 2.6 (14) |
C6B—N1B—C2B—N3B | −1.3 (12) | O11Y—C1Y—N2Y—C3Y | −1.2 (15) |
C6B—N1B—C2B—S21B | 178.2 (7) | O11Y—C1Y—N2Y—C4Y | 176.8 (9) |
N1B—C2B—N3B—C4B | 4.8 (12) | O11Z—C1Z—N2Z—C3Z | 2.0 (14) |
S21B—C2B—N3B—C4B | −174.7 (7) | O11Z—C1Z—N2Z—C4Z | −179.0 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O41B | 0.88 | 1.76 | 2.601 (7) | 160 |
N3A—H3A···O11X | 0.88 | 1.88 | 2.756 (7) | 170 |
N61A—H61A···O11W | 0.88 | 1.96 | 2.834 (9) | 172 |
N61A—H61B···O41B | 0.88 | 2.20 | 2.929 (8) | 140 |
N1B—H1B···O41Ai | 0.88 | 1.78 | 2.620 (7) | 159 |
N3B—H3B···O11Y | 0.88 | 1.87 | 2.738 (9) | 169 |
N61B—H61C···O11Z | 0.88 | 1.96 | 2.840 (8) | 174 |
N61B—H61D···O41Ai | 0.88 | 2.21 | 2.937 (7) | 140 |
Symmetry code: (i) x−1, y+1, z. |
C4H5N3OS·C4H9NO | F(000) = 488 |
Mr = 230.29 | Dx = 1.328 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 11701 reflections |
a = 9.4615 (9) Å | θ = 3.3–26.0° |
b = 9.2679 (11) Å | µ = 0.27 mm−1 |
c = 13.4208 (12) Å | T = 173 K |
β = 101.801 (7)° | Needle, colourless |
V = 1152.0 (2) Å3 | 0.50 × 0.30 × 0.25 mm |
Z = 4 |
Stoe IPDS II two-circle diffractometer | 2163 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1968 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.058 |
ω scans | θmax = 25.7°, θmin = 3.3° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −11→11 |
Tmin = 0.877, Tmax = 0.936 | k = −11→11 |
9565 measured reflections | l = −16→16 |
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) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0652P)2 + 0.3737P] where P = (Fo2 + 2Fc2)/3 |
2163 reflections | (Δ/σ)max = 0.001 |
171 parameters | Δρmax = 0.24 e Å−3 |
132 restraints | Δρmin = −0.19 e Å−3 |
C4H5N3OS·C4H9NO | V = 1152.0 (2) Å3 |
Mr = 230.29 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.4615 (9) Å | µ = 0.27 mm−1 |
b = 9.2679 (11) Å | T = 173 K |
c = 13.4208 (12) Å | 0.50 × 0.30 × 0.25 mm |
β = 101.801 (7)° |
Stoe IPDS II two-circle diffractometer | 2163 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1968 reflections with I > 2σ(I) |
Tmin = 0.877, Tmax = 0.936 | Rint = 0.058 |
9565 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 132 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.24 e Å−3 |
2163 reflections | Δρmin = −0.19 e Å−3 |
171 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.55570 (16) | 0.59050 (16) | 0.39081 (11) | 0.0342 (3) | |
H1A | 0.600 (2) | 0.506 (2) | 0.3933 (18) | 0.055 (7)* | |
C2A | 0.61035 (19) | 0.68598 (19) | 0.46532 (12) | 0.0335 (4) | |
S21A | 0.75963 (5) | 0.65062 (5) | 0.55106 (4) | 0.0449 (2) | |
N3A | 0.53623 (16) | 0.81059 (16) | 0.46367 (11) | 0.0346 (3) | |
H3A | 0.569 (2) | 0.877 (2) | 0.5102 (14) | 0.042 (5)* | |
C4A | 0.41399 (19) | 0.84740 (18) | 0.39141 (12) | 0.0338 (4) | |
O41A | 0.35918 (14) | 0.96886 (13) | 0.39965 (10) | 0.0413 (3) | |
C5A | 0.36411 (19) | 0.74546 (18) | 0.31586 (13) | 0.0351 (4) | |
H5A | 0.2811 | 0.7650 | 0.2646 | 0.042* | |
C6A | 0.43590 (18) | 0.61661 (19) | 0.31617 (12) | 0.0322 (4) | |
N61A | 0.40076 (18) | 0.51289 (17) | 0.24713 (12) | 0.0393 (4) | |
H61A | 0.452 (3) | 0.436 (2) | 0.2591 (19) | 0.056 (7)* | |
H62A | 0.319 (2) | 0.517 (3) | 0.2028 (16) | 0.052 (6)* | |
C1X | 0.8435 (3) | 0.2498 (3) | 0.4686 (2) | 0.0647 (6) | |
H1XA | 0.8975 | 0.1597 | 0.4849 | 0.097* | 0.610 (7) |
H1XB | 0.8026 | 0.2793 | 0.5269 | 0.097* | 0.610 (7) |
H1XC | 0.9084 | 0.3253 | 0.4534 | 0.097* | 0.610 (7) |
H1XD | 0.8439 | 0.1757 | 0.5358 | 0.097* | 0.390 (7) |
H1XE | 0.8209 | 0.3445 | 0.4835 | 0.097* | 0.390 (7) |
H1XF | 0.9485 | 0.2468 | 0.4504 | 0.097* | 0.390 (7) |
O21X | 0.6310 (2) | 0.32120 (16) | 0.33470 (14) | 0.0642 (5) | |
C31X | 0.5965 (3) | 0.0773 (3) | 0.2431 (2) | 0.0705 (7) | |
H31A | 0.5978 | −0.0222 | 0.2186 | 0.106* | 0.610 (7) |
H31B | 0.6130 | 0.1438 | 0.1898 | 0.106* | 0.610 (7) |
H31C | 0.5025 | 0.0978 | 0.2599 | 0.106* | 0.610 (7) |
H31D | 0.5540 | −0.0181 | 0.2644 | 0.106* | 0.390 (7) |
H31E | 0.5092 | 0.1523 | 0.2067 | 0.106* | 0.390 (7) |
H31F | 0.6686 | 0.0601 | 0.1985 | 0.106* | 0.390 (7) |
C32X | 0.8167 (4) | −0.0136 (3) | 0.3849 (3) | 0.0918 (11) | |
H32A | 0.7993 | −0.1055 | 0.3484 | 0.138* | 0.610 (7) |
H32B | 0.8057 | −0.0269 | 0.4554 | 0.138* | 0.610 (7) |
H32C | 0.9149 | 0.0197 | 0.3845 | 0.138* | 0.610 (7) |
H32D | 0.8999 | −0.0365 | 0.4392 | 0.138* | 0.390 (7) |
H32E | 0.8420 | −0.0300 | 0.3186 | 0.138* | 0.390 (7) |
H32F | 0.7352 | −0.0756 | 0.3915 | 0.138* | 0.390 (7) |
C2X | 0.7227 (4) | 0.2266 (4) | 0.3768 (3) | 0.0499 (11) | 0.610 (7) |
N3X | 0.7104 (4) | 0.0960 (4) | 0.3339 (3) | 0.0572 (11) | 0.610 (7) |
C2X' | 0.6633 (6) | 0.1892 (6) | 0.3245 (4) | 0.0499 (16) | 0.390 (7) |
N3X' | 0.7736 (6) | 0.1440 (5) | 0.3928 (4) | 0.0529 (16) | 0.390 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0335 (7) | 0.0310 (7) | 0.0339 (7) | 0.0017 (6) | −0.0032 (6) | 0.0001 (6) |
C2A | 0.0337 (9) | 0.0353 (8) | 0.0288 (8) | −0.0011 (7) | −0.0006 (7) | 0.0021 (7) |
S21A | 0.0404 (3) | 0.0457 (3) | 0.0394 (3) | 0.0058 (2) | −0.0134 (2) | 0.00078 (19) |
N3A | 0.0344 (8) | 0.0348 (8) | 0.0294 (7) | 0.0019 (6) | −0.0056 (6) | −0.0035 (6) |
C4A | 0.0325 (8) | 0.0361 (9) | 0.0296 (8) | 0.0014 (7) | −0.0014 (7) | 0.0004 (7) |
O41A | 0.0405 (7) | 0.0364 (7) | 0.0396 (7) | 0.0077 (5) | −0.0094 (5) | −0.0072 (5) |
C5A | 0.0323 (8) | 0.0354 (9) | 0.0322 (8) | 0.0026 (7) | −0.0060 (7) | −0.0015 (7) |
C6A | 0.0313 (8) | 0.0337 (8) | 0.0289 (8) | −0.0025 (7) | 0.0000 (6) | 0.0008 (6) |
N61A | 0.0385 (8) | 0.0344 (8) | 0.0389 (8) | 0.0019 (7) | −0.0061 (7) | −0.0065 (6) |
C1X | 0.0534 (13) | 0.0629 (15) | 0.0759 (16) | 0.0081 (11) | 0.0089 (12) | 0.0090 (12) |
O21X | 0.0694 (11) | 0.0403 (8) | 0.0792 (11) | 0.0183 (7) | 0.0062 (9) | 0.0029 (7) |
C31X | 0.094 (2) | 0.0541 (14) | 0.0690 (16) | −0.0075 (13) | 0.0294 (14) | −0.0104 (12) |
C32X | 0.108 (2) | 0.0596 (15) | 0.128 (3) | 0.0453 (16) | 0.070 (2) | 0.0368 (16) |
C2X | 0.052 (2) | 0.041 (2) | 0.059 (2) | 0.0054 (18) | 0.0185 (19) | 0.0067 (18) |
N3X | 0.076 (3) | 0.0396 (19) | 0.064 (2) | 0.0117 (17) | 0.0335 (19) | 0.0064 (15) |
C2X' | 0.059 (4) | 0.039 (3) | 0.058 (4) | 0.004 (3) | 0.024 (3) | 0.006 (3) |
N3X' | 0.057 (3) | 0.042 (3) | 0.063 (3) | 0.018 (2) | 0.020 (2) | 0.014 (2) |
N1A—C2A | 1.356 (2) | C1X—H1XF | 1.0705 |
N1A—C6A | 1.372 (2) | O21X—C2X' | 1.275 (5) |
N1A—H1A | 0.883 (17) | O21X—C2X | 1.280 (4) |
C2A—N3A | 1.349 (2) | C31X—N3X | 1.462 (5) |
C2A—S21A | 1.6618 (17) | C31X—C2X' | 1.545 (6) |
N3A—C4A | 1.391 (2) | C31X—H31A | 0.9800 |
N3A—H3A | 0.889 (16) | C31X—H31B | 0.9800 |
C4A—O41A | 1.254 (2) | C31X—H31C | 0.9800 |
C4A—C5A | 1.396 (2) | C31X—H31D | 1.0354 |
C5A—C6A | 1.373 (2) | C31X—H31E | 1.1135 |
C5A—H5A | 0.9500 | C31X—H31F | 1.0075 |
C6A—N61A | 1.329 (2) | C32X—N3X | 1.494 (4) |
N61A—H61A | 0.854 (17) | C32X—N3X' | 1.526 (5) |
N61A—H62A | 0.875 (17) | C32X—H32A | 0.9800 |
C1X—N3X' | 1.469 (6) | C32X—H32B | 0.9800 |
C1X—C2X | 1.514 (5) | C32X—H32C | 0.9800 |
C1X—H1XA | 0.9800 | C32X—H32D | 0.9800 |
C1X—H1XB | 0.9800 | C32X—H32E | 0.9800 |
C1X—H1XC | 0.9800 | C32X—H32F | 0.9801 |
C1X—H1XD | 1.1336 | C2X—N3X | 1.335 (5) |
C1X—H1XE | 0.9346 | C2X'—N3X' | 1.309 (7) |
C2A—N1A—C6A | 123.84 (15) | N3X—C31X—H31D | 97.6 |
C2A—N1A—H1A | 116.3 (16) | C2X'—C31X—H31D | 120.3 |
C6A—N1A—H1A | 119.9 (16) | H31A—C31X—H31D | 47.2 |
N3A—C2A—N1A | 115.35 (15) | H31B—C31X—H31D | 150.1 |
N3A—C2A—S21A | 123.06 (13) | H31C—C31X—H31D | 71.3 |
N1A—C2A—S21A | 121.59 (13) | N3X—C31X—H31E | 130.2 |
C2A—N3A—C4A | 125.21 (15) | C2X'—C31X—H31E | 92.9 |
C2A—N3A—H3A | 118.5 (14) | H31A—C31X—H31E | 120.0 |
C4A—N3A—H3A | 116.2 (14) | H31B—C31X—H31E | 60.1 |
O41A—C4A—N3A | 117.30 (15) | H31C—C31X—H31E | 49.7 |
O41A—C4A—C5A | 125.98 (16) | H31D—C31X—H31E | 111.0 |
N3A—C4A—C5A | 116.73 (15) | N3X—C31X—H31F | 92.3 |
C6A—C5A—C4A | 119.53 (16) | C2X'—C31X—H31F | 107.3 |
C6A—C5A—H5A | 120.2 | H31A—C31X—H31F | 66.2 |
C4A—C5A—H5A | 120.2 | H31B—C31X—H31F | 55.9 |
N61A—C6A—N1A | 115.65 (16) | H31C—C31X—H31F | 157.5 |
N61A—C6A—C5A | 125.00 (16) | H31D—C31X—H31F | 112.2 |
N1A—C6A—C5A | 119.33 (15) | H31E—C31X—H31F | 111.7 |
C6A—N61A—H61A | 114.8 (17) | N3X—C32X—H32A | 109.5 |
C6A—N61A—H62A | 120.3 (16) | N3X'—C32X—H32A | 147.9 |
H61A—N61A—H62A | 123 (2) | N3X—C32X—H32B | 109.5 |
N3X'—C1X—H1XA | 74.1 | N3X'—C32X—H32B | 88.3 |
C2X—C1X—H1XA | 109.5 | H32A—C32X—H32B | 109.5 |
N3X'—C1X—H1XB | 122.9 | N3X—C32X—H32C | 109.5 |
C2X—C1X—H1XB | 109.5 | N3X'—C32X—H32C | 88.1 |
H1XA—C1X—H1XB | 109.5 | H32A—C32X—H32C | 109.5 |
N3X'—C1X—H1XC | 123.1 | H32B—C32X—H32C | 109.5 |
C2X—C1X—H1XC | 109.5 | N3X—C32X—H32D | 148.4 |
H1XA—C1X—H1XC | 109.5 | N3X'—C32X—H32D | 110.0 |
H1XB—C1X—H1XC | 109.5 | H32A—C32X—H32D | 102.2 |
N3X'—C1X—H1XD | 94.3 | H32B—C32X—H32D | 58.9 |
C2X—C1X—H1XD | 116.1 | H32C—C32X—H32D | 57.0 |
H1XA—C1X—H1XD | 52.4 | N3X—C32X—H32E | 87.4 |
H1XB—C1X—H1XD | 58.1 | N3X'—C32X—H32E | 109.3 |
H1XC—C1X—H1XD | 134.3 | H32A—C32X—H32E | 57.2 |
N3X'—C1X—H1XE | 133.2 | H32B—C32X—H32E | 162.0 |
C2X—C1X—H1XE | 98.0 | H32C—C32X—H32E | 68.6 |
H1XA—C1X—H1XE | 152.1 | H32D—C32X—H32E | 109.5 |
H1XB—C1X—H1XE | 54.6 | N3X—C32X—H32F | 88.4 |
H1XC—C1X—H1XE | 63.6 | N3X'—C32X—H32F | 109.2 |
H1XD—C1X—H1XE | 111.2 | H32A—C32X—H32F | 58.7 |
N3X'—C1X—H1XF | 97.6 | H32B—C32X—H32F | 66.4 |
C2X—C1X—H1XF | 113.1 | H32C—C32X—H32F | 161.7 |
H1XA—C1X—H1XF | 64.0 | H32D—C32X—H32F | 109.5 |
H1XB—C1X—H1XF | 136.5 | H32E—C32X—H32F | 109.5 |
H1XC—C1X—H1XF | 47.2 | O21X—C2X—N3X | 116.0 (4) |
H1XD—C1X—H1XF | 108.2 | O21X—C2X—C1X | 126.3 (3) |
H1XE—C1X—H1XF | 109.7 | N3X—C2X—C1X | 117.6 (4) |
N3X—C31X—H31A | 109.5 | C2X—N3X—C31X | 116.8 (3) |
C2X'—C31X—H31A | 146.9 | C2X—N3X—C32X | 115.3 (4) |
N3X—C31X—H31B | 109.5 | C31X—N3X—C32X | 127.9 (3) |
C2X'—C31X—H31B | 89.4 | O21X—C2X'—N3X' | 113.9 (5) |
H31A—C31X—H31B | 109.5 | O21X—C2X'—C31X | 130.4 (5) |
N3X—C31X—H31C | 109.5 | N3X'—C2X'—C31X | 115.6 (5) |
C2X'—C31X—H31C | 88.1 | C2X'—N3X'—C1X | 116.9 (5) |
H31A—C31X—H31C | 109.5 | C2X'—N3X'—C32X | 116.3 (5) |
H31B—C31X—H31C | 109.5 | C1X—N3X'—C32X | 126.7 (4) |
C6A—N1A—C2A—N3A | 1.7 (2) | O21X—C2X—N3X—C32X | −179.1 (3) |
C6A—N1A—C2A—S21A | −177.59 (13) | C1X—C2X—N3X—C32X | 1.8 (4) |
N1A—C2A—N3A—C4A | −1.7 (3) | C2X'—C31X—N3X—C2X | −1.2 (4) |
S21A—C2A—N3A—C4A | 177.50 (13) | C2X'—C31X—N3X—C32X | 179.3 (6) |
C2A—N3A—C4A—O41A | −178.73 (16) | N3X'—C32X—N3X—C2X | −0.4 (4) |
C2A—N3A—C4A—C5A | 0.9 (3) | N3X'—C32X—N3X—C31X | 179.1 (5) |
O41A—C4A—C5A—C6A | 179.67 (17) | C2X—O21X—C2X'—N3X' | 0.1 (4) |
N3A—C4A—C5A—C6A | 0.0 (3) | C2X—O21X—C2X'—C31X | −177.7 (9) |
C2A—N1A—C6A—N61A | 177.63 (16) | N3X—C31X—C2X'—O21X | 178.7 (8) |
C2A—N1A—C6A—C5A | −0.8 (3) | N3X—C31X—C2X'—N3X' | 0.9 (4) |
C4A—C5A—C6A—N61A | −178.37 (17) | O21X—C2X'—N3X'—C1X | −0.8 (7) |
C4A—C5A—C6A—N1A | −0.1 (3) | C31X—C2X'—N3X'—C1X | 177.4 (4) |
C2X'—O21X—C2X—N3X | 0.4 (4) | O21X—C2X'—N3X'—C32X | 179.6 (4) |
C2X'—O21X—C2X—C1X | 179.4 (7) | C31X—C2X'—N3X'—C32X | −2.2 (6) |
N3X'—C1X—C2X—O21X | 180.0 (6) | C2X—C1X—N3X'—C2X' | 0.4 (4) |
N3X'—C1X—C2X—N3X | −1.0 (4) | C2X—C1X—N3X'—C32X | −180.0 (7) |
O21X—C2X—N3X—C31X | 1.3 (5) | N3X—C32X—N3X'—C2X' | 0.9 (4) |
C1X—C2X—N3X—C31X | −177.8 (3) | N3X—C32X—N3X'—C1X | −178.7 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.88 (2) | 1.94 (2) | 2.743 (2) | 151 (2) |
N3A—H3A···O41Ai | 0.89 (2) | 1.90 (2) | 2.7892 (19) | 175 (2) |
N61A—H61A···O21X | 0.85 (2) | 2.08 (2) | 2.870 (2) | 153 (2) |
N61A—H62A···O41Aii | 0.88 (2) | 2.00 (2) | 2.848 (2) | 165 (2) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |
2C4H5N3OS·3C4H9NO | F(000) = 1168 |
Mr = 547.71 | Dx = 1.316 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 10108 reflections |
a = 15.2133 (7) Å | θ = 3.3–25.5° |
b = 7.4335 (13) Å | µ = 0.24 mm−1 |
c = 24.445 (3) Å | T = 173 K |
V = 2764.4 (6) Å3 | Block, colourless |
Z = 4 | 0.27 × 0.20 × 0.15 mm |
Stoe IPDS II two-circle diffractometer | 5184 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 3323 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.149 |
ω scans | θmax = 25.7°, θmin = 3.3° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −18→18 |
Tmin = 0.938, Tmax = 0.965 | k = −8→9 |
33090 measured reflections | l = −29→29 |
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)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0318P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.002 |
5184 reflections | Δρmax = 0.32 e Å−3 |
378 parameters | Δρmin = −0.23 e Å−3 |
357 restraints | Absolute structure: Flack (1983), 2517 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (14) |
2C4H5N3OS·3C4H9NO | V = 2764.4 (6) Å3 |
Mr = 547.71 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 15.2133 (7) Å | µ = 0.24 mm−1 |
b = 7.4335 (13) Å | T = 173 K |
c = 24.445 (3) Å | 0.27 × 0.20 × 0.15 mm |
Stoe IPDS II two-circle diffractometer | 5184 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 3323 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 0.965 | Rint = 0.149 |
33090 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | Δρmax = 0.32 e Å−3 |
S = 0.93 | Δρmin = −0.23 e Å−3 |
5184 reflections | Absolute structure: Flack (1983), 2517 Friedel pairs |
378 parameters | Absolute structure parameter: 0.04 (14) |
357 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.6459 (2) | 0.4701 (6) | 0.50963 (18) | 0.0288 (10) | |
H1A | 0.6591 | 0.4824 | 0.5445 | 0.035* | |
C2A | 0.5682 (3) | 0.3950 (7) | 0.4973 (2) | 0.0285 (12) | |
S21A | 0.49462 (9) | 0.3386 (2) | 0.54470 (6) | 0.0381 (4) | |
N3A | 0.5543 (3) | 0.3711 (5) | 0.44364 (19) | 0.0255 (10) | |
H3A | 0.5051 | 0.3170 | 0.4344 | 0.031* | |
C4A | 0.6103 (3) | 0.4234 (7) | 0.4003 (2) | 0.0265 (11) | |
O41A | 0.5875 (2) | 0.3919 (5) | 0.35275 (16) | 0.0332 (8) | |
C5A | 0.6887 (3) | 0.5081 (7) | 0.4177 (2) | 0.0271 (11) | |
H5A | 0.7293 | 0.5507 | 0.3912 | 0.033* | |
C6A | 0.7067 (3) | 0.5293 (6) | 0.4720 (2) | 0.0228 (11) | |
N61A | 0.7783 (3) | 0.6033 (7) | 0.49197 (19) | 0.0351 (12) | |
H61A | 0.790 (3) | 0.610 (7) | 0.5276 (9) | 0.042* | |
H62A | 0.817 (3) | 0.648 (7) | 0.4698 (19) | 0.042* | |
N1B | 0.3412 (3) | 0.0983 (5) | 0.25494 (18) | 0.0281 (10) | |
H1B | 0.3297 | 0.0731 | 0.2205 | 0.034* | |
C2B | 0.4232 (3) | 0.1642 (7) | 0.2678 (2) | 0.0267 (12) | |
S21B | 0.49996 (10) | 0.1915 (2) | 0.22023 (6) | 0.0374 (3) | |
N3B | 0.4338 (3) | 0.2075 (5) | 0.32048 (18) | 0.0245 (10) | |
H3B | 0.4843 | 0.2569 | 0.3296 | 0.029* | |
C4B | 0.3726 (3) | 0.1822 (7) | 0.3627 (2) | 0.0247 (11) | |
O41B | 0.3932 (2) | 0.2292 (5) | 0.40996 (14) | 0.0308 (9) | |
C5B | 0.2923 (3) | 0.1114 (7) | 0.3467 (2) | 0.0283 (12) | |
H5B | 0.2477 | 0.0916 | 0.3732 | 0.034* | |
C6B | 0.2766 (3) | 0.0698 (7) | 0.2932 (2) | 0.0275 (12) | |
N61B | 0.2011 (3) | 0.0005 (7) | 0.2736 (2) | 0.0376 (12) | |
H61B | 0.196 (4) | 0.016 (8) | 0.2382 (9) | 0.045* | |
H62B | 0.158 (3) | −0.009 (8) | 0.2965 (19) | 0.045* | |
C1Z | 0.3625 (4) | 0.0639 (9) | 0.0882 (3) | 0.0470 (17) | |
H1Z1 | 0.3989 | 0.1064 | 0.1187 | 0.070* | |
H1Z2 | 0.3534 | 0.1624 | 0.0622 | 0.070* | |
H1Z3 | 0.3923 | −0.0360 | 0.0698 | 0.070* | |
O21Z | 0.2574 (3) | −0.0004 (7) | 0.16145 (18) | 0.0441 (10) | |
C2Z | 0.2747 (4) | 0.0007 (9) | 0.1098 (4) | 0.0516 (18) | |
N3Z | 0.2151 (4) | −0.0592 (8) | 0.0771 (3) | 0.0566 (16) | |
C31Z | 0.1306 (4) | −0.1228 (9) | 0.0950 (3) | 0.0494 (18) | |
H31A | 0.1287 | −0.1239 | 0.1351 | 0.074* | |
H31B | 0.1209 | −0.2449 | 0.0812 | 0.074* | |
H31C | 0.0846 | −0.0428 | 0.0810 | 0.074* | |
C32Z | 0.2311 (5) | −0.0701 (10) | 0.0162 (3) | 0.064 (2) | |
H32A | 0.2890 | −0.0199 | 0.0077 | 0.095* | |
H32B | 0.1857 | −0.0015 | −0.0031 | 0.095* | |
H32C | 0.2289 | −0.1962 | 0.0045 | 0.095* | |
C1X | 0.6418 (4) | 0.4062 (9) | 0.6774 (3) | 0.0440 (16) | |
H1XA | 0.6488 | 0.3842 | 0.7167 | 0.066* | 0.712 (11) |
H1XB | 0.6318 | 0.2917 | 0.6585 | 0.066* | 0.712 (11) |
H1XC | 0.5915 | 0.4860 | 0.6714 | 0.066* | 0.712 (11) |
H1XD | 0.6088 | 0.3649 | 0.7095 | 0.066* | 0.288 (11) |
H1XE | 0.6511 | 0.3051 | 0.6523 | 0.066* | 0.288 (11) |
H1XF | 0.6086 | 0.5009 | 0.6587 | 0.066* | 0.288 (11) |
O21X | 0.7347 (3) | 0.5321 (6) | 0.60636 (18) | 0.0472 (11) | |
C2X | 0.7240 (5) | 0.4935 (11) | 0.6553 (3) | 0.0267 (18) | 0.712 (11) |
N3X | 0.7880 (4) | 0.5295 (9) | 0.6904 (3) | 0.0281 (17) | 0.712 (11) |
C2X' | 0.7757 (9) | 0.538 (3) | 0.6535 (6) | 0.039 (5) | 0.288 (11) |
N3X' | 0.7280 (9) | 0.482 (3) | 0.6962 (5) | 0.047 (4) | 0.288 (11) |
C31X | 0.8683 (4) | 0.6132 (9) | 0.6691 (3) | 0.0468 (16) | |
H3XA | 0.9097 | 0.6332 | 0.6992 | 0.070* | 0.712 (11) |
H3XB | 0.8537 | 0.7286 | 0.6520 | 0.070* | 0.712 (11) |
H3XC | 0.8952 | 0.5336 | 0.6418 | 0.070* | 0.712 (11) |
H3XD | 0.8789 | 0.5921 | 0.7081 | 0.070* | 0.288 (11) |
H3XE | 0.8716 | 0.7424 | 0.6614 | 0.070* | 0.288 (11) |
H3XF | 0.9129 | 0.5497 | 0.6475 | 0.070* | 0.288 (11) |
C32X | 0.7796 (5) | 0.4840 (10) | 0.7493 (3) | 0.0557 (18) | |
H4XA | 0.8328 | 0.5216 | 0.7687 | 0.084* | 0.712 (11) |
H4XB | 0.7717 | 0.3538 | 0.7533 | 0.084* | 0.712 (11) |
H4XC | 0.7285 | 0.5465 | 0.7647 | 0.084* | 0.712 (11) |
H4XD | 0.7421 | 0.4404 | 0.7791 | 0.084* | 0.288 (11) |
H4XE | 0.7980 | 0.6077 | 0.7570 | 0.084* | 0.288 (11) |
H4XF | 0.8316 | 0.4069 | 0.7462 | 0.084* | 0.288 (11) |
C1Y | −0.0148 (4) | 0.2465 (8) | 0.3066 (2) | 0.0486 (15) | |
H1YA | −0.0652 | 0.3232 | 0.3155 | 0.073* | 0.630 (10) |
H1YB | −0.0336 | 0.1501 | 0.2819 | 0.073* | 0.630 (10) |
H1YC | 0.0308 | 0.3188 | 0.2888 | 0.073* | 0.630 (10) |
H1YD | −0.0602 | 0.3234 | 0.2906 | 0.073* | 0.370 (10) |
H1YE | −0.0175 | 0.1267 | 0.2899 | 0.073* | 0.370 (10) |
H1YF | 0.0432 | 0.2995 | 0.2999 | 0.073* | 0.370 (10) |
O21Y | 0.0864 (2) | 0.0569 (5) | 0.36316 (19) | 0.0492 (11) | |
C2Y | 0.0215 (5) | 0.1654 (12) | 0.3584 (4) | 0.032 (2) | 0.630 (10) |
N3Y | −0.0192 (4) | 0.2080 (9) | 0.4056 (3) | 0.035 (2) | 0.630 (10) |
C2Y' | 0.0290 (7) | 0.1299 (16) | 0.3929 (5) | 0.024 (3) | 0.370 (10) |
N3Y' | −0.0288 (8) | 0.2307 (15) | 0.3655 (5) | 0.032 (3) | 0.370 (10) |
C31Y | 0.0150 (4) | 0.1291 (8) | 0.4555 (2) | 0.0472 (15) | |
H3YA | −0.0195 | 0.1717 | 0.4868 | 0.071* | 0.630 (10) |
H3YB | 0.0766 | 0.1646 | 0.4602 | 0.071* | 0.630 (10) |
H3YC | 0.0111 | −0.0023 | 0.4532 | 0.071* | 0.630 (10) |
H3YD | −0.0381 | 0.1973 | 0.4647 | 0.071* | 0.370 (10) |
H3YE | 0.0661 | 0.1853 | 0.4730 | 0.071* | 0.370 (10) |
H3YF | 0.0089 | 0.0052 | 0.4686 | 0.071* | 0.370 (10) |
C32Y | −0.1010 (4) | 0.3118 (9) | 0.4018 (4) | 0.073 (2) | |
H4YA | −0.1235 | 0.3355 | 0.4387 | 0.110* | 0.630 (10) |
H4YB | −0.1446 | 0.2430 | 0.3810 | 0.110* | 0.630 (10) |
H4YC | −0.0894 | 0.4261 | 0.3832 | 0.110* | 0.630 (10) |
H4YD | −0.1407 | 0.3846 | 0.3794 | 0.110* | 0.370 (10) |
H4YE | −0.0743 | 0.3876 | 0.4301 | 0.110* | 0.370 (10) |
H4YF | −0.1341 | 0.2142 | 0.4192 | 0.110* | 0.370 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.025 (2) | 0.040 (3) | 0.021 (2) | −0.0017 (19) | −0.0053 (18) | 0.003 (2) |
C2A | 0.025 (2) | 0.033 (3) | 0.027 (3) | 0.007 (2) | −0.003 (2) | 0.003 (2) |
S21A | 0.0247 (7) | 0.0582 (9) | 0.0316 (9) | −0.0056 (7) | 0.0050 (7) | 0.0069 (7) |
N3A | 0.019 (2) | 0.030 (2) | 0.027 (3) | −0.0040 (17) | 0.0015 (17) | −0.0005 (19) |
C4A | 0.022 (2) | 0.025 (3) | 0.033 (3) | 0.004 (2) | −0.002 (2) | 0.002 (2) |
O41A | 0.0306 (18) | 0.043 (2) | 0.026 (2) | −0.0072 (16) | 0.0003 (16) | −0.0023 (18) |
C5A | 0.028 (2) | 0.031 (3) | 0.022 (3) | −0.002 (2) | 0.008 (2) | 0.000 (2) |
C6A | 0.017 (2) | 0.022 (3) | 0.030 (3) | 0.001 (2) | 0.003 (2) | 0.002 (2) |
N61A | 0.021 (2) | 0.061 (3) | 0.024 (3) | −0.010 (2) | 0.0027 (19) | 0.005 (3) |
N1B | 0.029 (2) | 0.034 (3) | 0.022 (2) | 0.0034 (19) | −0.0024 (18) | −0.003 (2) |
C2B | 0.024 (2) | 0.021 (3) | 0.035 (3) | 0.002 (2) | −0.003 (2) | 0.004 (2) |
S21B | 0.0290 (7) | 0.0534 (9) | 0.0299 (8) | −0.0019 (7) | 0.0055 (7) | 0.0043 (7) |
N3B | 0.023 (2) | 0.026 (2) | 0.024 (3) | −0.0036 (17) | 0.0006 (18) | −0.0032 (18) |
C4B | 0.022 (2) | 0.029 (3) | 0.024 (3) | 0.009 (2) | 0.005 (2) | 0.002 (2) |
O41B | 0.0219 (16) | 0.050 (2) | 0.021 (2) | −0.0019 (15) | −0.0006 (14) | −0.0005 (18) |
C5B | 0.023 (2) | 0.031 (3) | 0.030 (3) | 0.001 (2) | 0.008 (2) | 0.003 (2) |
C6B | 0.025 (2) | 0.025 (3) | 0.033 (3) | 0.008 (2) | −0.003 (2) | −0.001 (2) |
N61B | 0.024 (2) | 0.052 (3) | 0.036 (3) | −0.007 (2) | −0.003 (2) | −0.013 (3) |
C1Z | 0.044 (3) | 0.053 (4) | 0.045 (4) | −0.001 (3) | −0.003 (3) | −0.007 (3) |
O21Z | 0.043 (2) | 0.065 (3) | 0.025 (2) | 0.0127 (19) | −0.003 (2) | −0.007 (2) |
C2Z | 0.046 (4) | 0.032 (4) | 0.077 (6) | 0.017 (3) | −0.014 (4) | −0.006 (4) |
N3Z | 0.061 (4) | 0.059 (4) | 0.050 (4) | 0.006 (3) | −0.008 (3) | −0.008 (3) |
C31Z | 0.047 (4) | 0.057 (5) | 0.044 (4) | −0.024 (3) | −0.012 (3) | 0.001 (3) |
C32Z | 0.098 (5) | 0.068 (5) | 0.025 (4) | 0.015 (4) | −0.015 (4) | −0.009 (3) |
C1X | 0.034 (3) | 0.057 (4) | 0.041 (4) | 0.006 (3) | 0.003 (3) | −0.007 (3) |
O21X | 0.043 (2) | 0.074 (3) | 0.025 (2) | 0.004 (2) | −0.0035 (19) | 0.000 (2) |
C2X | 0.028 (4) | 0.038 (5) | 0.014 (4) | 0.009 (3) | 0.004 (3) | −0.002 (3) |
N3X | 0.028 (3) | 0.036 (4) | 0.020 (3) | 0.001 (3) | −0.007 (3) | −0.002 (3) |
C2X' | 0.023 (7) | 0.078 (13) | 0.017 (7) | 0.001 (8) | −0.005 (6) | 0.002 (9) |
N3X' | 0.049 (8) | 0.072 (11) | 0.020 (6) | −0.008 (8) | 0.007 (6) | −0.003 (8) |
C31X | 0.035 (3) | 0.055 (4) | 0.050 (4) | 0.006 (3) | −0.009 (3) | −0.010 (3) |
C32X | 0.079 (4) | 0.062 (4) | 0.027 (3) | 0.019 (4) | −0.006 (3) | 0.001 (3) |
C1Y | 0.054 (4) | 0.040 (3) | 0.052 (3) | −0.010 (3) | −0.011 (3) | 0.003 (3) |
O21Y | 0.0283 (19) | 0.054 (3) | 0.066 (3) | 0.0030 (18) | 0.0065 (18) | −0.021 (2) |
C2Y | 0.027 (4) | 0.033 (5) | 0.035 (4) | −0.013 (4) | 0.000 (4) | −0.015 (4) |
N3Y | 0.033 (4) | 0.029 (4) | 0.043 (4) | −0.002 (3) | 0.011 (3) | −0.013 (4) |
C2Y' | 0.019 (6) | 0.017 (7) | 0.035 (6) | −0.015 (4) | 0.007 (5) | 0.000 (6) |
N3Y' | 0.034 (6) | 0.015 (6) | 0.046 (6) | 0.005 (5) | −0.002 (5) | −0.008 (6) |
C31Y | 0.052 (4) | 0.056 (4) | 0.034 (3) | −0.017 (3) | 0.007 (3) | −0.002 (3) |
C32Y | 0.040 (3) | 0.048 (4) | 0.133 (7) | 0.008 (3) | 0.019 (4) | −0.018 (5) |
N1A—C2A | 1.342 (6) | C1X—H1XF | 0.9801 |
N1A—C6A | 1.377 (6) | O21X—C2X | 1.241 (8) |
N1A—H1A | 0.8800 | O21X—C2X' | 1.311 (13) |
C2A—N3A | 1.341 (7) | C2X—N3X | 1.325 (9) |
C2A—S21A | 1.664 (5) | N3X—C31X | 1.467 (8) |
N3A—C4A | 1.412 (6) | N3X—C32X | 1.485 (8) |
N3A—H3A | 0.8800 | C2X'—N3X' | 1.337 (16) |
C4A—O41A | 1.236 (7) | C2X'—C31X | 1.563 (13) |
C4A—C5A | 1.414 (7) | N3X'—C32X | 1.517 (12) |
C5A—C6A | 1.364 (7) | C31X—H3XA | 0.9800 |
C5A—H5A | 0.9500 | C31X—H3XB | 0.9800 |
C6A—N61A | 1.315 (6) | C31X—H3XC | 0.9800 |
N61A—H61A | 0.891 (19) | C31X—H3XD | 0.9799 |
N61A—H62A | 0.87 (2) | C31X—H3XE | 0.9800 |
N1B—C6B | 1.374 (7) | C31X—H3XF | 0.9798 |
N1B—C2B | 1.376 (6) | C32X—H4XA | 0.9800 |
N1B—H1B | 0.8800 | C32X—H4XB | 0.9800 |
C2B—N3B | 1.337 (7) | C32X—H4XC | 0.9800 |
C2B—S21B | 1.661 (5) | C32X—H4XD | 0.9800 |
N3B—C4B | 1.403 (6) | C32X—H4XE | 0.9800 |
N3B—H3B | 0.8800 | C32X—H4XF | 0.9801 |
C4B—O41B | 1.247 (6) | C1Y—N3Y' | 1.459 (12) |
C4B—C5B | 1.387 (6) | C1Y—C2Y | 1.507 (10) |
C5B—C6B | 1.365 (8) | C1Y—H1YA | 0.9800 |
C5B—H5B | 0.9500 | C1Y—H1YB | 0.9800 |
C6B—N61B | 1.347 (6) | C1Y—H1YC | 0.9800 |
N61B—H61B | 0.879 (19) | C1Y—H1YD | 0.9799 |
N61B—H62B | 0.869 (19) | C1Y—H1YE | 0.9800 |
C1Z—C2Z | 1.512 (9) | C1Y—H1YF | 0.9801 |
C1Z—H1Z1 | 0.9800 | O21Y—C2Y' | 1.260 (11) |
C1Z—H1Z2 | 0.9800 | O21Y—C2Y | 1.281 (9) |
C1Z—H1Z3 | 0.9800 | C2Y—N3Y | 1.347 (10) |
O21Z—C2Z | 1.289 (9) | N3Y—C31Y | 1.450 (9) |
C2Z—N3Z | 1.288 (9) | N3Y—C32Y | 1.466 (8) |
N3Z—C31Z | 1.439 (8) | C2Y'—N3Y' | 1.335 (14) |
N3Z—C32Z | 1.512 (8) | C2Y'—C31Y | 1.546 (12) |
C31Z—H31A | 0.9800 | N3Y'—C32Y | 1.535 (11) |
C31Z—H31B | 0.9800 | C31Y—H3YA | 0.9800 |
C31Z—H31C | 0.9800 | C31Y—H3YB | 0.9800 |
C32Z—H32A | 0.9800 | C31Y—H3YC | 0.9800 |
C32Z—H32B | 0.9800 | C31Y—H3YD | 0.9800 |
C32Z—H32C | 0.9800 | C31Y—H3YE | 0.9800 |
C1X—N3X' | 1.499 (13) | C31Y—H3YF | 0.9801 |
C1X—C2X | 1.509 (9) | C32Y—H4YA | 0.9800 |
C1X—H1XA | 0.9800 | C32Y—H4YB | 0.9800 |
C1X—H1XB | 0.9800 | C32Y—H4YC | 0.9800 |
C1X—H1XC | 0.9800 | C32Y—H4YD | 0.9800 |
C1X—H1XD | 0.9801 | C32Y—H4YE | 0.9801 |
C1X—H1XE | 0.9800 | C32Y—H4YF | 0.9800 |
C2A—N1A—C6A | 125.1 (5) | C2X'—C31X—H3XF | 108.7 |
C2A—N1A—H1A | 117.4 | H3XA—C31X—H3XF | 91.9 |
C6A—N1A—H1A | 117.4 | H3XB—C31X—H3XF | 110.4 |
N1A—C2A—N3A | 114.4 (5) | H3XD—C31X—H3XF | 109.5 |
N1A—C2A—S21A | 122.8 (4) | H3XE—C31X—H3XF | 109.5 |
N3A—C2A—S21A | 122.8 (4) | N3X—C32X—H4XA | 109.5 |
C2A—N3A—C4A | 127.0 (4) | N3X'—C32X—H4XA | 147.7 |
C2A—N3A—H3A | 116.5 | N3X—C32X—H4XB | 109.5 |
C4A—N3A—H3A | 116.5 | N3X'—C32X—H4XB | 90.8 |
O41A—C4A—N3A | 119.0 (4) | H4XA—C32X—H4XB | 109.5 |
O41A—C4A—C5A | 127.1 (5) | N3X—C32X—H4XC | 109.5 |
N3A—C4A—C5A | 113.9 (5) | N3X'—C32X—H4XC | 85.6 |
C6A—C5A—C4A | 120.9 (4) | H4XA—C32X—H4XC | 109.5 |
C6A—C5A—H5A | 119.5 | H4XB—C32X—H4XC | 109.5 |
C4A—C5A—H5A | 119.5 | N3X—C32X—H4XD | 147.8 |
N61A—C6A—C5A | 125.2 (5) | N3X'—C32X—H4XD | 109.4 |
N61A—C6A—N1A | 116.2 (5) | H4XA—C32X—H4XD | 102.4 |
C5A—C6A—N1A | 118.5 (4) | H4XB—C32X—H4XD | 61.9 |
C6A—N61A—H61A | 124 (4) | H4XC—C32X—H4XD | 53.8 |
C6A—N61A—H62A | 119 (4) | N3X—C32X—H4XE | 87.0 |
H61A—N61A—H62A | 117 (5) | N3X'—C32X—H4XE | 108.7 |
C6B—N1B—C2B | 123.2 (4) | H4XA—C32X—H4XE | 53.3 |
C6B—N1B—H1B | 118.4 | H4XB—C32X—H4XE | 160.4 |
C2B—N1B—H1B | 118.4 | H4XC—C32X—H4XE | 73.0 |
N3B—C2B—N1B | 114.6 (4) | H4XD—C32X—H4XE | 109.5 |
N3B—C2B—S21B | 124.0 (4) | N3X—C32X—H4XF | 89.4 |
N1B—C2B—S21B | 121.4 (4) | N3X'—C32X—H4XF | 110.3 |
C2B—N3B—C4B | 126.6 (4) | H4XA—C32X—H4XF | 62.4 |
C2B—N3B—H3B | 116.7 | H4XB—C32X—H4XF | 61.8 |
C4B—N3B—H3B | 116.7 | H4XC—C32X—H4XF | 161.1 |
O41B—C4B—C5B | 126.2 (4) | H4XD—C32X—H4XF | 109.5 |
O41B—C4B—N3B | 118.5 (4) | H4XE—C32X—H4XF | 109.5 |
C5B—C4B—N3B | 115.3 (5) | N3Y'—C1Y—H1YA | 73.4 |
C6B—C5B—C4B | 120.7 (4) | C2Y—C1Y—H1YA | 109.5 |
C6B—C5B—H5B | 119.6 | N3Y'—C1Y—H1YB | 120.4 |
C4B—C5B—H5B | 119.6 | C2Y—C1Y—H1YB | 109.5 |
N61B—C6B—C5B | 125.2 (5) | H1YA—C1Y—H1YB | 109.5 |
N61B—C6B—N1B | 115.3 (5) | N3Y'—C1Y—H1YC | 125.9 |
C5B—C6B—N1B | 119.5 (4) | C2Y—C1Y—H1YC | 109.5 |
C6B—N61B—H61B | 112 (4) | H1YA—C1Y—H1YC | 109.5 |
C6B—N61B—H62B | 117 (4) | H1YB—C1Y—H1YC | 109.5 |
H61B—N61B—H62B | 125 (5) | N3Y'—C1Y—H1YD | 109.8 |
C2Z—C1Z—H1Z1 | 109.5 | C2Y—C1Y—H1YD | 146.0 |
C2Z—C1Z—H1Z2 | 109.5 | H1YB—C1Y—H1YD | 88.5 |
H1Z1—C1Z—H1Z2 | 109.5 | H1YC—C1Y—H1YD | 90.1 |
C2Z—C1Z—H1Z3 | 109.5 | N3Y'—C1Y—H1YE | 109.4 |
H1Z1—C1Z—H1Z3 | 109.5 | C2Y—C1Y—H1YE | 90.2 |
H1Z2—C1Z—H1Z3 | 109.5 | H1YA—C1Y—H1YE | 126.0 |
O21Z—C2Z—N3Z | 117.5 (7) | H1YC—C1Y—H1YE | 110.0 |
O21Z—C2Z—C1Z | 121.6 (6) | H1YD—C1Y—H1YE | 109.5 |
N3Z—C2Z—C1Z | 120.8 (8) | N3Y'—C1Y—H1YF | 109.2 |
C2Z—N3Z—C31Z | 123.6 (7) | C2Y—C1Y—H1YF | 88.4 |
C2Z—N3Z—C32Z | 121.2 (7) | H1YA—C1Y—H1YF | 120.5 |
C31Z—N3Z—C32Z | 115.2 (6) | H1YB—C1Y—H1YF | 117.0 |
N3Z—C31Z—H31A | 109.5 | H1YD—C1Y—H1YF | 109.5 |
N3Z—C31Z—H31B | 109.5 | H1YE—C1Y—H1YF | 109.5 |
H31A—C31Z—H31B | 109.5 | O21Y—C2Y—N3Y | 115.2 (8) |
N3Z—C31Z—H31C | 109.5 | O21Y—C2Y—C1Y | 127.6 (7) |
H31A—C31Z—H31C | 109.5 | N3Y—C2Y—C1Y | 117.2 (7) |
H31B—C31Z—H31C | 109.5 | C2Y—N3Y—C31Y | 117.4 (6) |
N3Z—C32Z—H32A | 109.5 | C2Y—N3Y—C32Y | 117.4 (7) |
N3Z—C32Z—H32B | 109.5 | C31Y—N3Y—C32Y | 124.8 (6) |
H32A—C32Z—H32B | 109.5 | C2Y—N3Y—H3YD | 156.3 |
N3Z—C32Z—H32C | 109.5 | C32Y—N3Y—H3YD | 85.7 |
H32A—C32Z—H32C | 109.5 | O21Y—C2Y'—N3Y' | 114.2 (10) |
H32B—C32Z—H32C | 109.5 | O21Y—C2Y'—C31Y | 131.7 (10) |
N3X'—C1X—H1XA | 70.6 | N3Y'—C2Y'—C31Y | 114.1 (9) |
C2X—C1X—H1XA | 109.5 | C2Y'—N3Y'—C1Y | 116.3 (9) |
N3X'—C1X—H1XB | 127.4 | C2Y'—N3Y'—C32Y | 113.6 (9) |
C2X—C1X—H1XB | 109.5 | C1Y—N3Y'—C32Y | 130.1 (9) |
H1XA—C1X—H1XB | 109.5 | N3Y—C31Y—H3YA | 109.5 |
N3X'—C1X—H1XC | 120.1 | C2Y'—C31Y—H3YA | 147.7 |
C2X—C1X—H1XC | 109.5 | N3Y—C31Y—H3YB | 109.5 |
H1XA—C1X—H1XC | 109.5 | C2Y'—C31Y—H3YB | 89.1 |
H1XB—C1X—H1XC | 109.5 | H3YA—C31Y—H3YB | 109.5 |
N3X'—C1X—H1XD | 108.8 | N3Y—C31Y—H3YC | 109.5 |
C2X—C1X—H1XD | 147.8 | C2Y'—C31Y—H3YC | 87.5 |
H1XB—C1X—H1XD | 91.4 | H3YA—C31Y—H3YC | 109.5 |
H1XC—C1X—H1XD | 84.8 | H3YB—C31Y—H3YC | 109.5 |
N3X'—C1X—H1XE | 110.8 | N3Y—C31Y—H3YD | 71.8 |
C2X—C1X—H1XE | 89.2 | C2Y'—C31Y—H3YD | 109.8 |
H1XA—C1X—H1XE | 118.0 | H3YB—C31Y—H3YD | 128.4 |
H1XC—C1X—H1XE | 118.8 | H3YC—C31Y—H3YD | 118.6 |
H1XD—C1X—H1XE | 109.5 | N3Y—C31Y—H3YE | 118.6 |
N3X'—C1X—H1XF | 108.9 | C2Y'—C31Y—H3YE | 108.7 |
C2X—C1X—H1XF | 87.2 | H3YA—C31Y—H3YE | 87.0 |
H1XA—C1X—H1XF | 129.3 | H3YC—C31Y—H3YE | 119.9 |
H1XB—C1X—H1XF | 108.9 | H3YD—C31Y—H3YE | 109.5 |
H1XD—C1X—H1XF | 109.5 | N3Y—C31Y—H3YF | 128.4 |
H1XE—C1X—H1XF | 109.5 | C2Y'—C31Y—H3YF | 109.9 |
O21X—C2X—N3X | 118.8 (7) | H3YA—C31Y—H3YF | 89.9 |
O21X—C2X—C1X | 123.6 (6) | H3YB—C31Y—H3YF | 107.8 |
N3X—C2X—C1X | 117.6 (6) | H3YD—C31Y—H3YF | 109.5 |
C2X—N3X—C31X | 117.9 (6) | H3YE—C31Y—H3YF | 109.5 |
C2X—N3X—C32X | 121.2 (6) | N3Y—C32Y—H4YA | 109.5 |
C31X—N3X—C32X | 120.9 (6) | N3Y'—C32Y—H4YA | 148.5 |
O21X—C2X'—N3X' | 114.6 (11) | N3Y—C32Y—H4YB | 109.5 |
O21X—C2X'—C31X | 130.9 (11) | N3Y'—C32Y—H4YB | 88.8 |
N3X'—C2X'—C31X | 114.2 (11) | H4YA—C32Y—H4YB | 109.5 |
C2X'—N3X'—C1X | 110.7 (10) | N3Y—C32Y—H4YC | 109.5 |
C2X'—N3X'—C32X | 112.6 (11) | N3Y'—C32Y—H4YC | 86.8 |
C1X—N3X'—C32X | 135.9 (10) | H4YA—C32Y—H4YC | 109.5 |
N3X—C31X—H3XA | 109.5 | H4YB—C32Y—H4YC | 109.5 |
C2X'—C31X—H3XA | 144.8 | N3Y—C32Y—H4YD | 148.2 |
N3X—C31X—H3XB | 109.5 | N3Y'—C32Y—H4YD | 109.5 |
C2X'—C31X—H3XB | 90.3 | H4YA—C32Y—H4YD | 101.5 |
H3XA—C31X—H3XB | 109.5 | H4YB—C32Y—H4YD | 65.1 |
N3X—C31X—H3XC | 109.5 | H4YC—C32Y—H4YD | 51.1 |
C2X'—C31X—H3XC | 89.7 | N3Y—C32Y—H4YE | 84.6 |
H3XA—C31X—H3XC | 109.5 | N3Y'—C32Y—H4YE | 109.7 |
H3XB—C31X—H3XC | 109.5 | H4YA—C32Y—H4YE | 52.6 |
N3X—C31X—H3XD | 74.0 | H4YB—C32Y—H4YE | 161.2 |
C2X'—C31X—H3XD | 109.2 | H4YC—C32Y—H4YE | 75.8 |
H3XB—C31X—H3XD | 126.3 | H4YD—C32Y—H4YE | 109.5 |
H3XC—C31X—H3XD | 119.8 | N3Y—C32Y—H4YF | 91.1 |
N3X—C31X—H3XE | 121.7 | N3Y'—C32Y—H4YF | 109.2 |
C2X'—C31X—H3XE | 110.5 | H4YA—C32Y—H4YF | 63.6 |
H3XA—C31X—H3XE | 87.8 | H4YB—C32Y—H4YF | 59.3 |
H3XC—C31X—H3XE | 116.2 | H4YC—C32Y—H4YF | 159.3 |
H3XD—C31X—H3XE | 109.5 | H4YD—C32Y—H4YF | 109.5 |
N3X—C31X—H3XF | 124.3 | H4YE—C32Y—H4YF | 109.5 |
C6A—N1A—C2A—N3A | 3.5 (7) | O21X—C2X'—N3X'—C1X | 7 (3) |
C6A—N1A—C2A—S21A | −175.8 (4) | C31X—C2X'—N3X'—C1X | −177.9 (13) |
N1A—C2A—N3A—C4A | −3.1 (7) | O21X—C2X'—N3X'—C32X | 177.6 (15) |
S21A—C2A—N3A—C4A | 176.2 (4) | C31X—C2X'—N3X'—C32X | −7 (2) |
C2A—N3A—C4A—O41A | −179.7 (5) | C2X—C1X—N3X'—C2X' | −1.8 (12) |
C2A—N3A—C4A—C5A | 0.6 (7) | C2X—C1X—N3X'—C32X | −170 (3) |
O41A—C4A—C5A—C6A | −177.9 (5) | C2X—N3X—C31X—C2X' | −1.0 (16) |
N3A—C4A—C5A—C6A | 1.8 (7) | C32X—N3X—C31X—C2X' | 177.9 (18) |
C4A—C5A—C6A—N61A | 178.8 (5) | O21X—C2X'—C31X—N3X | 178 (3) |
C4A—C5A—C6A—N1A | −1.5 (7) | N3X'—C2X'—C31X—N3X | 3.1 (10) |
C2A—N1A—C6A—N61A | 178.4 (5) | C2X—N3X—C32X—N3X' | −4.6 (14) |
C2A—N1A—C6A—C5A | −1.4 (7) | C31X—N3X—C32X—N3X' | 176.5 (14) |
C6B—N1B—C2B—N3B | −3.2 (7) | C2X'—N3X'—C32X—N3X | 2.3 (13) |
C6B—N1B—C2B—S21B | 178.5 (4) | C1X—N3X'—C32X—N3X | 170 (3) |
N1B—C2B—N3B—C4B | 4.0 (7) | C2Y'—O21Y—C2Y—N3Y | 2.3 (9) |
S21B—C2B—N3B—C4B | −177.7 (4) | C2Y'—O21Y—C2Y—C1Y | −176.4 (16) |
C2B—N3B—C4B—O41B | 179.5 (5) | N3Y'—C1Y—C2Y—O21Y | 174.4 (14) |
C2B—N3B—C4B—C5B | −2.7 (7) | N3Y'—C1Y—C2Y—N3Y | −4.2 (10) |
O41B—C4B—C5B—C6B | 178.0 (5) | O21Y—C2Y—N3Y—C31Y | 0.6 (9) |
N3B—C4B—C5B—C6B | 0.5 (7) | C1Y—C2Y—N3Y—C31Y | 179.5 (6) |
C4B—C5B—C6B—N61B | 179.9 (5) | O21Y—C2Y—N3Y—C32Y | −171.9 (6) |
C4B—C5B—C6B—N1B | 0.1 (7) | C1Y—C2Y—N3Y—C32Y | 6.9 (9) |
C2B—N1B—C6B—N61B | −178.5 (5) | C2Y—O21Y—C2Y'—N3Y' | 3.2 (8) |
C2B—N1B—C6B—C5B | 1.4 (7) | C2Y—O21Y—C2Y'—C31Y | −174 (2) |
O21Z—C2Z—N3Z—C31Z | 1.5 (10) | O21Y—C2Y'—N3Y'—C1Y | −2.3 (15) |
C1Z—C2Z—N3Z—C31Z | 179.5 (6) | C31Y—C2Y'—N3Y'—C1Y | 175.7 (8) |
O21Z—C2Z—N3Z—C32Z | −177.4 (6) | O21Y—C2Y'—N3Y'—C32Y | 177.3 (8) |
C1Z—C2Z—N3Z—C32Z | 0.5 (10) | C31Y—C2Y'—N3Y'—C32Y | −4.6 (14) |
C2X'—O21X—C2X—N3X | 1.2 (17) | C2Y—C1Y—N3Y'—C2Y' | −1.4 (9) |
C2X'—O21X—C2X—C1X | −178 (2) | C2Y—C1Y—N3Y'—C32Y | 179.0 (18) |
N3X'—C1X—C2X—O21X | −176.2 (17) | C2Y—N3Y—C31Y—C2Y' | −2.4 (9) |
N3X'—C1X—C2X—N3X | 4.1 (13) | C32Y—N3Y—C31Y—C2Y' | 169.5 (11) |
O21X—C2X—N3X—C31X | −0.2 (11) | O21Y—C2Y'—C31Y—N3Y | 175.0 (18) |
C1X—C2X—N3X—C31X | 179.6 (6) | N3Y'—C2Y'—C31Y—N3Y | −2.6 (9) |
O21X—C2X—N3X—C32X | −179.1 (7) | C2Y—N3Y—C32Y—N3Y' | −1.2 (8) |
C1X—C2X—N3X—C32X | 0.6 (10) | C31Y—N3Y—C32Y—N3Y' | −173.1 (13) |
C2X—O21X—C2X'—N3X' | −3.2 (12) | C2Y'—N3Y'—C32Y—N3Y | 6.2 (7) |
C2X—O21X—C2X'—C31X | −178 (3) | C1Y—N3Y'—C32Y—N3Y | −174.2 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O21Z | 0.88 | 1.90 | 2.718 (6) | 155 |
N3B—H3B···O41A | 0.88 | 1.95 | 2.823 (5) | 173 |
N61B—H61B···O21Z | 0.88 (2) | 2.10 (4) | 2.873 (7) | 146 (5) |
N61B—H62B···O21Y | 0.87 (2) | 2.02 (3) | 2.830 (7) | 155 (6) |
N1A—H1A···O21X | 0.88 | 1.94 | 2.761 (6) | 156 |
N3A—H3A···O41B | 0.88 | 1.92 | 2.792 (5) | 172 |
N61A—H61A···O21X | 0.89 (2) | 2.18 (4) | 2.922 (6) | 140 (5) |
N61A—H62A···O41Bi | 0.87 (2) | 2.08 (2) | 2.937 (6) | 171 (5) |
Symmetry code: (i) x+1/2, −y+1, z. |
2C4H5N3OS·3C5H9NO | F(000) = 1240 |
Mr = 583.74 | Dx = 1.339 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 28863 reflections |
a = 15.2293 (10) Å | θ = 2.4–26.4° |
b = 7.5483 (4) Å | µ = 0.23 mm−1 |
c = 25.1871 (13) Å | T = 173 K |
V = 2895.4 (3) Å3 | Plate, colourless |
Z = 4 | 0.34 × 0.28 × 0.16 mm |
Stoe IPDS II two-circle diffractometer | 4332 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 3541 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.053 |
ω scans | θmax = 24.8°, θmin = 2.7° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −14→17 |
Tmin = 0.925, Tmax = 0.964 | k = −8→8 |
8280 measured reflections | l = −29→25 |
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)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.066P)2 + 4.3455P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4332 reflections | Δρmax = 0.36 e Å−3 |
474 parameters | Δρmin = −0.34 e Å−3 |
569 restraints | Absolute structure: Flack (1983), 1810 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (15) |
2C4H5N3OS·3C5H9NO | V = 2895.4 (3) Å3 |
Mr = 583.74 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 15.2293 (10) Å | µ = 0.23 mm−1 |
b = 7.5483 (4) Å | T = 173 K |
c = 25.1871 (13) Å | 0.34 × 0.28 × 0.16 mm |
Stoe IPDS II two-circle diffractometer | 4332 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 3541 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 0.964 | Rint = 0.053 |
8280 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.170 | Δρmax = 0.36 e Å−3 |
S = 1.06 | Δρmin = −0.34 e Å−3 |
4332 reflections | Absolute structure: Flack (1983), 1810 Friedel pairs |
474 parameters | Absolute structure parameter: 0.12 (15) |
569 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.6639 (3) | 0.4991 (7) | 0.63829 (18) | 0.0438 (11) | |
H1A | 0.6749 | 0.5243 | 0.6717 | 0.053* | |
C2A | 0.5864 (3) | 0.4207 (8) | 0.6264 (2) | 0.0439 (13) | |
S21A | 0.51259 (9) | 0.3814 (3) | 0.67358 (8) | 0.0591 (4) | |
N3A | 0.5747 (3) | 0.3810 (6) | 0.57501 (19) | 0.0404 (10) | |
H3A | 0.5256 | 0.3263 | 0.5665 | 0.048* | |
C4A | 0.6339 (3) | 0.4189 (7) | 0.5331 (2) | 0.0394 (12) | |
O41A | 0.6111 (2) | 0.3789 (5) | 0.48797 (16) | 0.0475 (9) | |
C5A | 0.7116 (3) | 0.5072 (7) | 0.5483 (2) | 0.0445 (13) | |
H5A | 0.7531 | 0.5422 | 0.5222 | 0.053* | |
C6A | 0.7269 (3) | 0.5420 (7) | 0.6006 (2) | 0.0398 (13) | |
N61A | 0.7985 (3) | 0.6218 (7) | 0.6200 (2) | 0.0575 (14) | |
H61A | 0.8405 | 0.6564 | 0.5983 | 0.069* | |
H61B | 0.8036 | 0.6396 | 0.6544 | 0.069* | |
N1B | 0.3617 (3) | 0.0813 (6) | 0.3959 (2) | 0.0453 (11) | |
H1B | 0.3491 | 0.0488 | 0.3632 | 0.054* | |
C2B | 0.4426 (4) | 0.1516 (7) | 0.4056 (2) | 0.0432 (13) | |
S21B | 0.51735 (10) | 0.1701 (2) | 0.35892 (7) | 0.0552 (4) | |
N3B | 0.4562 (3) | 0.2013 (6) | 0.45640 (19) | 0.0390 (10) | |
H3B | 0.5077 | 0.2475 | 0.4642 | 0.047* | |
C4B | 0.3950 (3) | 0.1855 (7) | 0.4980 (3) | 0.0440 (14) | |
O41B | 0.4182 (2) | 0.2408 (6) | 0.54357 (16) | 0.0467 (9) | |
C5B | 0.3140 (3) | 0.1124 (7) | 0.4854 (3) | 0.0446 (13) | |
H5B | 0.2701 | 0.1003 | 0.5119 | 0.054* | |
C6B | 0.2980 (3) | 0.0582 (7) | 0.4348 (3) | 0.0445 (14) | |
N61B | 0.2220 (3) | −0.0180 (7) | 0.4177 (2) | 0.0614 (15) | |
H61C | 0.1786 | −0.0355 | 0.4402 | 0.074* | |
H61D | 0.2164 | −0.0498 | 0.3843 | 0.074* | |
N1X | 0.8041 (3) | 0.5650 (7) | 0.81512 (19) | 0.0548 (12) | |
C11X | 0.8907 (4) | 0.6303 (11) | 0.8028 (3) | 0.071 (2) | |
H11A | 0.8936 | 0.6617 | 0.7651 | 0.106* | |
H11B | 0.9342 | 0.5381 | 0.8105 | 0.106* | |
H11C | 0.9031 | 0.7353 | 0.8244 | 0.106* | |
C2X | 0.7416 (3) | 0.5532 (8) | 0.7794 (2) | 0.0554 (15) | |
O21X | 0.7504 (3) | 0.5829 (7) | 0.73126 (16) | 0.0633 (12) | |
C3X | 0.6576 (4) | 0.4962 (10) | 0.8067 (2) | 0.0659 (18) | |
H3X1 | 0.6139 | 0.5931 | 0.8065 | 0.079* | |
H3X2 | 0.6320 | 0.3911 | 0.7890 | 0.079* | |
C4X | 0.6853 (4) | 0.4527 (9) | 0.8624 (3) | 0.0742 (19) | |
H4X1 | 0.6851 | 0.3229 | 0.8680 | 0.089* | |
H4X2 | 0.6448 | 0.5079 | 0.8883 | 0.089* | |
C5X | 0.7784 (4) | 0.5273 (9) | 0.8690 (2) | 0.0643 (17) | |
H5X1 | 0.7782 | 0.6363 | 0.8909 | 0.077* | |
H5X2 | 0.8180 | 0.4391 | 0.8854 | 0.077* | |
N1Y | −0.0051 (6) | 0.2275 (15) | 0.4881 (3) | 0.057 (3) | 0.623 (13) |
C11Y | 0.0214 (8) | 0.2611 (17) | 0.4340 (4) | 0.063 (3) | 0.623 (13) |
H1YA | −0.0252 | 0.2225 | 0.4098 | 0.095* | 0.623 (13) |
H1YB | 0.0754 | 0.1953 | 0.4263 | 0.095* | 0.623 (13) |
H1YC | 0.0319 | 0.3882 | 0.4292 | 0.095* | 0.623 (13) |
C2Y | 0.0422 (8) | 0.133 (2) | 0.5218 (4) | 0.052 (3) | 0.623 (13) |
O21Y | 0.1109 (9) | 0.0542 (19) | 0.5129 (6) | 0.061 (3) | 0.623 (13) |
C3Y | −0.0001 (9) | 0.149 (2) | 0.5772 (4) | 0.070 (3) | 0.623 (13) |
H3YA | −0.0084 | 0.0303 | 0.5934 | 0.084* | 0.623 (13) |
H3YB | 0.0365 | 0.2220 | 0.6011 | 0.084* | 0.623 (13) |
C4Y | −0.0861 (9) | 0.235 (2) | 0.5665 (5) | 0.068 (4) | 0.623 (13) |
H4YA | −0.0981 | 0.3274 | 0.5935 | 0.082* | 0.623 (13) |
H4YB | −0.1340 | 0.1468 | 0.5675 | 0.082* | 0.623 (13) |
C5Y | −0.0794 (8) | 0.318 (2) | 0.5112 (5) | 0.069 (4) | 0.623 (13) |
H5YA | −0.1335 | 0.2973 | 0.4903 | 0.083* | 0.623 (13) |
H5YB | −0.0687 | 0.4476 | 0.5135 | 0.083* | 0.623 (13) |
N1Y' | 0.0013 (10) | 0.171 (3) | 0.5493 (5) | 0.058 (4) | 0.377 (13) |
C1Y' | 0.0288 (16) | 0.093 (3) | 0.5988 (7) | 0.085 (7) | 0.377 (13) |
H1YD | −0.0153 | 0.1167 | 0.6262 | 0.128* | 0.377 (13) |
H1YE | 0.0853 | 0.1435 | 0.6096 | 0.128* | 0.377 (13) |
H1YF | 0.0351 | −0.0356 | 0.5942 | 0.128* | 0.377 (13) |
C2Y' | 0.0486 (15) | 0.161 (4) | 0.5054 (7) | 0.065 (6) | 0.377 (13) |
O2Y' | 0.1064 (17) | 0.052 (4) | 0.4965 (10) | 0.092 (9) | 0.377 (13) |
C3Y' | −0.0017 (13) | 0.257 (3) | 0.4611 (6) | 0.064 (5) | 0.377 (13) |
H3YC | 0.0336 | 0.3560 | 0.4466 | 0.077* | 0.377 (13) |
H3YD | −0.0159 | 0.1741 | 0.4319 | 0.077* | 0.377 (13) |
C4Y' | −0.0833 (16) | 0.325 (4) | 0.4863 (7) | 0.063 (5) | 0.377 (13) |
H4YC | −0.1356 | 0.2706 | 0.4694 | 0.076* | 0.377 (13) |
H4YD | −0.0871 | 0.4549 | 0.4824 | 0.076* | 0.377 (13) |
C5Y' | −0.0786 (12) | 0.273 (3) | 0.5457 (7) | 0.054 (5) | 0.377 (13) |
H5YC | −0.0759 | 0.3793 | 0.5685 | 0.064* | 0.377 (13) |
H5YD | −0.1301 | 0.2006 | 0.5561 | 0.064* | 0.377 (13) |
O21Z | 0.2718 (3) | −0.0272 (8) | 0.30892 (18) | 0.0793 (15) | |
N1Z | 0.3020 (5) | −0.0182 (13) | 0.2228 (3) | 0.075 (3) | 0.678 (11) |
C11Z | 0.3901 (7) | 0.050 (2) | 0.2285 (5) | 0.084 (4) | 0.678 (11) |
H1ZA | 0.4273 | 0.0010 | 0.2003 | 0.127* | 0.678 (11) |
H1ZB | 0.4136 | 0.0147 | 0.2632 | 0.127* | 0.678 (11) |
H1ZC | 0.3892 | 0.1791 | 0.2259 | 0.127* | 0.678 (11) |
C2Z | 0.2500 (8) | −0.045 (4) | 0.2632 (3) | 0.072 (3) | 0.678 (11) |
C3Z | 0.1615 (7) | −0.112 (3) | 0.2436 (4) | 0.079 (3) | 0.678 (11) |
H3ZA | 0.1514 | −0.2356 | 0.2549 | 0.095* | 0.678 (11) |
H3ZB | 0.1133 | −0.0366 | 0.2574 | 0.095* | 0.678 (11) |
C4Z | 0.1675 (8) | −0.099 (2) | 0.1846 (4) | 0.106 (4) | 0.678 (11) |
H4ZA | 0.1255 | −0.0097 | 0.1711 | 0.128* | 0.678 (11) |
H4ZB | 0.1534 | −0.2148 | 0.1682 | 0.128* | 0.678 (11) |
C5Z | 0.2621 (10) | −0.044 (4) | 0.1710 (4) | 0.087 (4) | 0.678 (11) |
H5ZA | 0.2926 | −0.1390 | 0.1509 | 0.104* | 0.678 (11) |
H5ZB | 0.2632 | 0.0662 | 0.1499 | 0.104* | 0.678 (11) |
N1Z' | 0.2188 (9) | −0.072 (3) | 0.2230 (5) | 0.067 (4) | 0.322 (11) |
C1Z' | 0.1291 (12) | −0.111 (7) | 0.2365 (11) | 0.104 (11) | 0.322 (11) |
H1ZD | 0.0965 | −0.1422 | 0.2042 | 0.156* | 0.322 (11) |
H1ZE | 0.1021 | −0.0073 | 0.2531 | 0.156* | 0.322 (11) |
H1ZF | 0.1274 | −0.2113 | 0.2613 | 0.156* | 0.322 (11) |
C2Z' | 0.2785 (13) | −0.032 (8) | 0.2592 (4) | 0.063 (5) | 0.322 (11) |
C3Z' | 0.3645 (11) | −0.006 (5) | 0.2283 (7) | 0.085 (7) | 0.322 (11) |
H3ZC | 0.3953 | 0.1023 | 0.2407 | 0.102* | 0.322 (11) |
H3ZD | 0.4038 | −0.1087 | 0.2332 | 0.102* | 0.322 (11) |
C4Z' | 0.3385 (14) | 0.013 (4) | 0.1707 (7) | 0.093 (6) | 0.322 (11) |
H4ZC | 0.3795 | −0.0528 | 0.1474 | 0.112* | 0.322 (11) |
H4ZD | 0.3380 | 0.1391 | 0.1598 | 0.112* | 0.322 (11) |
C5Z' | 0.245 (2) | −0.067 (9) | 0.1678 (5) | 0.080 (6) | 0.322 (11) |
H5ZC | 0.2055 | 0.0092 | 0.1467 | 0.096* | 0.322 (11) |
H5ZD | 0.2464 | −0.1871 | 0.1521 | 0.096* | 0.322 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.036 (2) | 0.065 (3) | 0.031 (3) | 0.003 (2) | 0.0009 (18) | 0.001 (2) |
C2A | 0.034 (3) | 0.048 (3) | 0.050 (4) | 0.001 (2) | −0.005 (2) | 0.003 (3) |
S21A | 0.0399 (7) | 0.0913 (12) | 0.0462 (9) | −0.0033 (7) | 0.0062 (7) | 0.0085 (9) |
N3A | 0.030 (2) | 0.049 (3) | 0.042 (3) | −0.0034 (18) | −0.0004 (18) | 0.006 (2) |
C4A | 0.042 (3) | 0.037 (3) | 0.039 (3) | 0.006 (2) | −0.001 (2) | 0.001 (3) |
O41A | 0.051 (2) | 0.057 (2) | 0.034 (2) | −0.0017 (18) | 0.0010 (17) | −0.001 (2) |
C5A | 0.035 (3) | 0.050 (3) | 0.048 (4) | 0.001 (2) | 0.005 (2) | 0.002 (3) |
C6A | 0.034 (3) | 0.043 (3) | 0.042 (3) | 0.007 (2) | −0.001 (2) | 0.001 (3) |
N61A | 0.042 (2) | 0.086 (4) | 0.045 (3) | −0.012 (2) | 0.006 (2) | −0.005 (3) |
N1B | 0.041 (2) | 0.043 (2) | 0.052 (3) | 0.007 (2) | −0.009 (2) | −0.009 (2) |
C2B | 0.050 (3) | 0.034 (3) | 0.045 (4) | 0.008 (2) | −0.011 (2) | −0.002 (3) |
S21B | 0.0517 (8) | 0.0682 (10) | 0.0456 (9) | −0.0001 (7) | 0.0017 (7) | 0.0000 (8) |
N3B | 0.033 (2) | 0.040 (2) | 0.044 (3) | 0.0024 (17) | −0.0008 (19) | 0.002 (2) |
C4B | 0.031 (2) | 0.041 (3) | 0.060 (4) | 0.006 (2) | 0.004 (2) | 0.007 (3) |
O41B | 0.0360 (18) | 0.061 (2) | 0.043 (3) | 0.0005 (17) | 0.0007 (16) | −0.003 (2) |
C5B | 0.039 (3) | 0.039 (3) | 0.056 (4) | 0.002 (2) | 0.000 (2) | −0.002 (3) |
C6B | 0.039 (3) | 0.034 (3) | 0.060 (4) | 0.005 (2) | −0.008 (3) | −0.004 (3) |
N61B | 0.034 (2) | 0.075 (4) | 0.075 (4) | −0.005 (2) | −0.001 (3) | −0.022 (3) |
N1X | 0.061 (3) | 0.062 (3) | 0.042 (3) | 0.015 (2) | −0.001 (2) | −0.002 (3) |
C11X | 0.060 (4) | 0.080 (5) | 0.073 (5) | −0.005 (3) | −0.006 (3) | 0.011 (4) |
C2X | 0.059 (3) | 0.057 (4) | 0.049 (3) | 0.009 (3) | −0.002 (3) | −0.007 (3) |
O21X | 0.050 (2) | 0.101 (4) | 0.039 (2) | −0.004 (2) | −0.0051 (18) | −0.002 (2) |
C3X | 0.061 (4) | 0.074 (5) | 0.063 (4) | 0.009 (3) | 0.007 (3) | 0.000 (4) |
C4X | 0.088 (4) | 0.055 (4) | 0.079 (5) | 0.011 (3) | 0.023 (4) | 0.017 (4) |
C5X | 0.076 (4) | 0.071 (4) | 0.046 (4) | 0.011 (3) | 0.002 (3) | 0.011 (4) |
N1Y | 0.045 (5) | 0.055 (6) | 0.071 (6) | −0.004 (4) | 0.014 (5) | −0.005 (6) |
C11Y | 0.076 (8) | 0.054 (7) | 0.060 (7) | −0.014 (6) | 0.017 (6) | −0.007 (6) |
C2Y | 0.046 (5) | 0.045 (6) | 0.066 (7) | −0.020 (4) | 0.005 (5) | −0.010 (6) |
O21Y | 0.059 (6) | 0.060 (6) | 0.063 (7) | −0.006 (4) | 0.001 (5) | −0.011 (6) |
C3Y | 0.074 (7) | 0.067 (9) | 0.069 (8) | −0.025 (6) | 0.015 (7) | −0.010 (8) |
C4Y | 0.072 (6) | 0.063 (9) | 0.070 (9) | −0.013 (6) | 0.031 (6) | −0.017 (8) |
C5Y | 0.054 (6) | 0.050 (8) | 0.103 (12) | −0.004 (5) | 0.028 (8) | −0.009 (11) |
N1Y' | 0.044 (7) | 0.063 (9) | 0.066 (9) | −0.001 (6) | 0.004 (7) | −0.006 (9) |
C1Y' | 0.108 (17) | 0.077 (16) | 0.071 (11) | 0.009 (11) | −0.029 (11) | −0.005 (11) |
C2Y' | 0.058 (10) | 0.058 (13) | 0.081 (10) | 0.005 (9) | 0.021 (8) | −0.019 (10) |
O2Y' | 0.043 (8) | 0.113 (15) | 0.12 (2) | 0.021 (8) | −0.010 (10) | −0.079 (13) |
C3Y' | 0.071 (10) | 0.057 (11) | 0.064 (12) | −0.027 (8) | 0.017 (10) | −0.009 (13) |
C4Y' | 0.083 (10) | 0.040 (10) | 0.066 (13) | 0.003 (8) | −0.001 (10) | −0.004 (11) |
C5Y' | 0.045 (8) | 0.046 (12) | 0.071 (13) | 0.005 (8) | 0.019 (9) | 0.004 (12) |
O21Z | 0.080 (3) | 0.101 (4) | 0.057 (3) | −0.003 (3) | −0.023 (3) | −0.014 (3) |
N1Z | 0.107 (6) | 0.062 (5) | 0.056 (5) | 0.011 (5) | −0.021 (5) | −0.013 (5) |
C11Z | 0.112 (8) | 0.078 (11) | 0.063 (8) | 0.006 (8) | 0.008 (6) | −0.015 (7) |
C2Z | 0.089 (8) | 0.064 (8) | 0.064 (5) | 0.005 (9) | −0.032 (5) | −0.003 (7) |
C3Z | 0.086 (8) | 0.083 (8) | 0.067 (6) | 0.018 (8) | −0.039 (6) | −0.011 (7) |
C4Z | 0.137 (9) | 0.118 (10) | 0.065 (7) | −0.010 (9) | −0.040 (7) | 0.004 (8) |
C5Z | 0.121 (9) | 0.080 (11) | 0.060 (6) | 0.035 (8) | −0.028 (6) | −0.006 (8) |
N1Z' | 0.078 (8) | 0.070 (9) | 0.052 (7) | −0.002 (8) | −0.010 (6) | −0.002 (8) |
C1Z' | 0.060 (12) | 0.13 (2) | 0.12 (2) | 0.001 (18) | −0.024 (11) | 0.03 (2) |
C2Z' | 0.067 (10) | 0.061 (12) | 0.061 (7) | 0.000 (13) | −0.012 (7) | −0.017 (12) |
C3Z' | 0.078 (11) | 0.089 (18) | 0.087 (10) | −0.007 (14) | 0.006 (8) | −0.042 (13) |
C4Z' | 0.104 (12) | 0.089 (14) | 0.087 (10) | 0.019 (11) | 0.027 (10) | 0.002 (13) |
C5Z' | 0.113 (13) | 0.074 (14) | 0.052 (8) | 0.022 (13) | −0.010 (9) | −0.027 (12) |
N1A—C2A | 1.355 (7) | C3Y—H3YB | 0.9900 |
N1A—C6A | 1.388 (7) | C4Y—C5Y | 1.531 (9) |
N1A—H1A | 0.8800 | C4Y—H4YA | 0.9900 |
C2A—N3A | 1.340 (7) | C4Y—H4YB | 0.9900 |
C2A—S21A | 1.663 (6) | C5Y—H5YA | 0.9900 |
N3A—C4A | 1.417 (7) | C5Y—H5YB | 0.9900 |
N3A—H3A | 0.8800 | N1Y'—C2Y' | 1.322 (8) |
C4A—O41A | 1.227 (6) | N1Y'—C5Y' | 1.441 (8) |
C4A—C5A | 1.411 (7) | N1Y'—C1Y' | 1.443 (9) |
C5A—C6A | 1.362 (8) | C1Y'—H1YD | 0.9800 |
C5A—H5A | 0.9500 | C1Y'—H1YE | 0.9800 |
C6A—N61A | 1.338 (7) | C1Y'—H1YF | 0.9800 |
N61A—H61A | 0.8800 | C2Y'—O2Y' | 1.230 (9) |
N61A—H61B | 0.8800 | C2Y'—C3Y' | 1.534 (9) |
N1B—C2B | 1.363 (7) | C3Y'—C4Y' | 1.485 (9) |
N1B—C6B | 1.389 (8) | C3Y'—H3YC | 0.9900 |
N1B—H1B | 0.8800 | C3Y'—H3YD | 0.9900 |
C2B—N3B | 1.349 (7) | C4Y'—C5Y' | 1.548 (9) |
C2B—S21B | 1.643 (6) | C4Y'—H4YC | 0.9900 |
N3B—C4B | 1.408 (7) | C4Y'—H4YD | 0.9900 |
N3B—H3B | 0.8800 | C5Y'—H5YC | 0.9900 |
C4B—O41B | 1.271 (7) | C5Y'—H5YD | 0.9900 |
C4B—C5B | 1.388 (7) | O21Z—C2Z | 1.207 (7) |
C5B—C6B | 1.360 (8) | O21Z—C2Z' | 1.257 (8) |
C5B—H5B | 0.9500 | N1Z—C2Z | 1.305 (8) |
C6B—N61B | 1.362 (7) | N1Z—C11Z | 1.443 (8) |
N61B—H61C | 0.8800 | N1Z—C5Z | 1.454 (8) |
N61B—H61D | 0.8800 | C11Z—H1ZA | 0.9800 |
N1X—C2X | 1.313 (6) | C11Z—H1ZB | 0.9800 |
N1X—C5X | 1.440 (6) | C11Z—H1ZC | 0.9800 |
N1X—C11X | 1.442 (6) | C2Z—C3Z | 1.519 (8) |
C11X—H11A | 0.9800 | C3Z—C4Z | 1.492 (8) |
C11X—H11B | 0.9800 | C3Z—H3ZA | 0.9900 |
C11X—H11C | 0.9800 | C3Z—H3ZB | 0.9900 |
C2X—O21X | 1.240 (6) | C4Z—C5Z | 1.538 (9) |
C2X—C3X | 1.515 (6) | C4Z—H4ZA | 0.9900 |
C3X—C4X | 1.501 (7) | C4Z—H4ZB | 0.9900 |
C3X—H3X1 | 0.9900 | C5Z—H5ZA | 0.9900 |
C3X—H3X2 | 0.9900 | C5Z—H5ZB | 0.9900 |
C4X—C5X | 1.535 (7) | N1Z'—C2Z' | 1.324 (8) |
C4X—H4X1 | 0.9900 | N1Z'—C1Z' | 1.438 (9) |
C4X—H4X2 | 0.9900 | N1Z'—C5Z' | 1.448 (9) |
C5X—H5X1 | 0.9900 | C1Z'—H1ZD | 0.9800 |
C5X—H5X2 | 0.9900 | C1Z'—H1ZE | 0.9800 |
N1Y—C2Y | 1.322 (8) | C1Z'—H1ZF | 0.9800 |
N1Y—C11Y | 1.444 (8) | C2Z'—C3Z' | 1.537 (9) |
N1Y—C5Y | 1.445 (8) | C3Z'—C4Z' | 1.510 (10) |
C11Y—H1YA | 0.9800 | C3Z'—H3ZC | 0.9900 |
C11Y—H1YB | 0.9800 | C3Z'—H3ZD | 0.9900 |
C11Y—H1YC | 0.9800 | C4Z'—C5Z' | 1.543 (10) |
C2Y—O21Y | 1.225 (8) | C4Z'—H4ZC | 0.9900 |
C2Y—C3Y | 1.540 (8) | C4Z'—H4ZD | 0.9900 |
C3Y—C4Y | 1.488 (9) | C5Z'—H5ZC | 0.9900 |
C3Y—H3YA | 0.9900 | C5Z'—H5ZD | 0.9900 |
C2A—N1A—C6A | 123.6 (5) | N1Y—C5Y—C4Y | 102.8 (7) |
C2A—N1A—H1A | 118.2 | N1Y—C5Y—H5YA | 111.2 |
C6A—N1A—H1A | 118.2 | C4Y—C5Y—H5YA | 111.2 |
N3A—C2A—N1A | 115.3 (5) | N1Y—C5Y—H5YB | 111.2 |
N3A—C2A—S21A | 124.1 (4) | C4Y—C5Y—H5YB | 111.2 |
N1A—C2A—S21A | 120.6 (5) | H5YA—C5Y—H5YB | 109.1 |
C2A—N3A—C4A | 126.1 (5) | C2Y'—N1Y'—C5Y' | 116.0 (8) |
C2A—N3A—H3A | 117.0 | C2Y'—N1Y'—C1Y' | 122.7 (11) |
C4A—N3A—H3A | 117.0 | C5Y'—N1Y'—C1Y' | 121.3 (11) |
O41A—C4A—C5A | 127.3 (5) | N1Y'—C1Y'—H1YD | 109.5 |
O41A—C4A—N3A | 117.4 (5) | N1Y'—C1Y'—H1YE | 109.5 |
C5A—C4A—N3A | 115.3 (5) | H1YD—C1Y'—H1YE | 109.5 |
C6A—C5A—C4A | 119.8 (5) | N1Y'—C1Y'—H1YF | 109.5 |
C6A—C5A—H5A | 120.1 | H1YD—C1Y'—H1YF | 109.5 |
C4A—C5A—H5A | 120.1 | H1YE—C1Y'—H1YF | 109.5 |
N61A—C6A—C5A | 125.4 (5) | O2Y'—C2Y'—N1Y' | 125.6 (15) |
N61A—C6A—N1A | 114.7 (5) | O2Y'—C2Y'—C3Y' | 122.8 (14) |
C5A—C6A—N1A | 119.9 (5) | N1Y'—C2Y'—C3Y' | 108.0 (8) |
C6A—N61A—H61A | 120.0 | C4Y'—C3Y'—C2Y' | 105.6 (8) |
C6A—N61A—H61B | 120.0 | C4Y'—C3Y'—H3YC | 110.6 |
H61A—N61A—H61B | 120.0 | C2Y'—C3Y'—H3YC | 110.6 |
C2B—N1B—C6B | 123.6 (5) | C4Y'—C3Y'—H3YD | 110.6 |
C2B—N1B—H1B | 118.2 | C2Y'—C3Y'—H3YD | 110.6 |
C6B—N1B—H1B | 118.2 | H3YC—C3Y'—H3YD | 108.7 |
N3B—C2B—N1B | 114.6 (5) | C3Y'—C4Y'—C5Y' | 106.7 (8) |
N3B—C2B—S21B | 123.3 (4) | C3Y'—C4Y'—H4YC | 110.4 |
N1B—C2B—S21B | 122.1 (4) | C5Y'—C4Y'—H4YC | 110.4 |
C2B—N3B—C4B | 125.5 (5) | C3Y'—C4Y'—H4YD | 110.4 |
C2B—N3B—H3B | 117.2 | C5Y'—C4Y'—H4YD | 110.4 |
C4B—N3B—H3B | 117.2 | H4YC—C4Y'—H4YD | 108.6 |
O41B—C4B—C5B | 125.8 (5) | N1Y'—C5Y'—C4Y' | 103.6 (8) |
O41B—C4B—N3B | 117.4 (5) | N1Y'—C5Y'—H5YC | 111.0 |
C5B—C4B—N3B | 116.8 (6) | C4Y'—C5Y'—H5YC | 111.0 |
C6B—C5B—C4B | 119.6 (6) | N1Y'—C5Y'—H5YD | 111.0 |
C6B—C5B—H5B | 120.2 | C4Y'—C5Y'—H5YD | 111.0 |
C4B—C5B—H5B | 120.2 | H5YC—C5Y'—H5YD | 109.0 |
C5B—C6B—N61B | 125.1 (6) | C2Z—N1Z—C11Z | 122.9 (8) |
C5B—C6B—N1B | 119.8 (5) | C2Z—N1Z—C5Z | 115.1 (7) |
N61B—C6B—N1B | 115.1 (6) | C11Z—N1Z—C5Z | 121.7 (8) |
C6B—N61B—H61C | 120.0 | O21Z—C2Z—N1Z | 123.9 (8) |
C6B—N61B—H61D | 120.0 | O21Z—C2Z—C3Z | 126.2 (8) |
H61C—N61B—H61D | 120.0 | N1Z—C2Z—C3Z | 109.7 (7) |
C2X—N1X—C5X | 115.8 (5) | C4Z—C3Z—C2Z | 104.4 (7) |
C2X—N1X—C11X | 122.6 (5) | C4Z—C3Z—H3ZA | 110.9 |
C5X—N1X—C11X | 121.3 (5) | C2Z—C3Z—H3ZA | 110.9 |
N1X—C11X—H11A | 109.5 | C4Z—C3Z—H3ZB | 110.9 |
N1X—C11X—H11B | 109.5 | C2Z—C3Z—H3ZB | 110.9 |
H11A—C11X—H11B | 109.5 | H3ZA—C3Z—H3ZB | 108.9 |
N1X—C11X—H11C | 109.5 | C3Z—C4Z—C5Z | 107.2 (7) |
H11A—C11X—H11C | 109.5 | C3Z—C4Z—H4ZA | 110.3 |
H11B—C11X—H11C | 109.5 | C5Z—C4Z—H4ZA | 110.3 |
O21X—C2X—N1X | 125.4 (5) | C3Z—C4Z—H4ZB | 110.3 |
O21X—C2X—C3X | 125.9 (5) | C5Z—C4Z—H4ZB | 110.3 |
N1X—C2X—C3X | 108.6 (5) | H4ZA—C4Z—H4ZB | 108.5 |
C4X—C3X—C2X | 104.5 (5) | N1Z—C5Z—C4Z | 103.2 (7) |
C4X—C3X—H3X1 | 110.9 | N1Z—C5Z—H5ZA | 111.1 |
C2X—C3X—H3X1 | 110.9 | C4Z—C5Z—H5ZA | 111.1 |
C4X—C3X—H3X2 | 110.9 | N1Z—C5Z—H5ZB | 111.1 |
C2X—C3X—H3X2 | 110.9 | C4Z—C5Z—H5ZB | 111.1 |
H3X1—C3X—H3X2 | 108.9 | H5ZA—C5Z—H5ZB | 109.1 |
C3X—C4X—C5X | 106.2 (5) | C2Z'—N1Z'—C1Z' | 122.5 (12) |
C3X—C4X—H4X1 | 110.5 | C2Z'—N1Z'—C5Z' | 117.6 (8) |
C5X—C4X—H4X1 | 110.5 | C1Z'—N1Z'—C5Z' | 119.8 (11) |
C3X—C4X—H4X2 | 110.5 | N1Z'—C1Z'—H1ZD | 109.5 |
C5X—C4X—H4X2 | 110.5 | N1Z'—C1Z'—H1ZE | 109.5 |
H4X1—C4X—H4X2 | 108.7 | H1ZD—C1Z'—H1ZE | 109.5 |
N1X—C5X—C4X | 102.8 (5) | N1Z'—C1Z'—H1ZF | 109.5 |
N1X—C5X—H5X1 | 111.2 | H1ZD—C1Z'—H1ZF | 109.5 |
C4X—C5X—H5X1 | 111.2 | H1ZE—C1Z'—H1ZF | 109.5 |
N1X—C5X—H5X2 | 111.2 | O21Z—C2Z'—N1Z' | 129.6 (11) |
C4X—C5X—H5X2 | 111.2 | O21Z—C2Z'—C3Z' | 124.8 (11) |
H5X1—C5X—H5X2 | 109.1 | N1Z'—C2Z'—C3Z' | 105.4 (8) |
C2Y—N1Y—C11Y | 123.3 (8) | C4Z'—C3Z'—C2Z' | 106.0 (9) |
C2Y—N1Y—C5Y | 115.1 (7) | C4Z'—C3Z'—H3ZC | 110.5 |
C11Y—N1Y—C5Y | 121.0 (8) | C2Z'—C3Z'—H3ZC | 110.5 |
O21Y—C2Y—N1Y | 127.6 (9) | C4Z'—C3Z'—H3ZD | 110.5 |
O21Y—C2Y—C3Y | 124.1 (9) | C2Z'—C3Z'—H3ZD | 110.5 |
N1Y—C2Y—C3Y | 108.2 (7) | H3ZC—C3Z'—H3ZD | 108.7 |
C4Y—C3Y—C2Y | 103.7 (7) | C3Z'—C4Z'—C5Z' | 104.5 (10) |
C4Y—C3Y—H3YA | 111.0 | C3Z'—C4Z'—H4ZC | 110.9 |
C2Y—C3Y—H3YA | 111.0 | C5Z'—C4Z'—H4ZC | 110.9 |
C4Y—C3Y—H3YB | 111.0 | C3Z'—C4Z'—H4ZD | 110.9 |
C2Y—C3Y—H3YB | 111.0 | C5Z'—C4Z'—H4ZD | 110.9 |
H3YA—C3Y—H3YB | 109.0 | H4ZC—C4Z'—H4ZD | 108.9 |
C3Y—C4Y—C5Y | 106.7 (7) | N1Z'—C5Z'—C4Z' | 102.9 (9) |
C3Y—C4Y—H4YA | 110.4 | N1Z'—C5Z'—H5ZC | 111.2 |
C5Y—C4Y—H4YA | 110.4 | C4Z'—C5Z'—H5ZC | 111.2 |
C3Y—C4Y—H4YB | 110.4 | N1Z'—C5Z'—H5ZD | 111.2 |
C5Y—C4Y—H4YB | 110.4 | C4Z'—C5Z'—H5ZD | 111.2 |
H4YA—C4Y—H4YB | 108.6 | H5ZC—C5Z'—H5ZD | 109.1 |
C6A—N1A—C2A—N3A | 1.9 (8) | N1Y—C2Y—C3Y—C4Y | 10.7 (17) |
C6A—N1A—C2A—S21A | −177.4 (4) | C2Y—C3Y—C4Y—C5Y | −17.4 (18) |
N1A—C2A—N3A—C4A | −2.3 (8) | C2Y—N1Y—C5Y—C4Y | −11.8 (18) |
S21A—C2A—N3A—C4A | 177.0 (4) | C11Y—N1Y—C5Y—C4Y | 176.9 (14) |
C2A—N3A—C4A—O41A | −177.3 (5) | C3Y—C4Y—C5Y—N1Y | 17.9 (18) |
C2A—N3A—C4A—C5A | −0.2 (8) | C5Y'—N1Y'—C2Y'—O2Y' | −162 (3) |
O41A—C4A—C5A—C6A | 179.9 (5) | C1Y'—N1Y'—C2Y'—O2Y' | 20 (5) |
N3A—C4A—C5A—C6A | 3.1 (7) | C5Y'—N1Y'—C2Y'—C3Y' | −3 (3) |
C4A—C5A—C6A—N61A | 178.8 (5) | C1Y'—N1Y'—C2Y'—C3Y' | 179 (2) |
C4A—C5A—C6A—N1A | −3.5 (8) | O2Y'—C2Y'—C3Y'—C4Y' | 160 (3) |
C2A—N1A—C6A—N61A | 178.8 (5) | N1Y'—C2Y'—C3Y'—C4Y' | 1 (3) |
C2A—N1A—C6A—C5A | 0.9 (8) | C2Y'—C3Y'—C4Y'—C5Y' | 2 (3) |
C6B—N1B—C2B—N3B | −1.2 (7) | C2Y'—N1Y'—C5Y'—C4Y' | 4 (3) |
C6B—N1B—C2B—S21B | 177.7 (4) | C1Y'—N1Y'—C5Y'—C4Y' | −178 (3) |
N1B—C2B—N3B—C4B | 0.1 (7) | C3Y'—C4Y'—C5Y'—N1Y' | −3 (3) |
S21B—C2B—N3B—C4B | −178.8 (4) | C2Z'—O21Z—C2Z—N1Z | −3 (9) |
C2B—N3B—C4B—O41B | −179.3 (5) | C2Z'—O21Z—C2Z—C3Z | 173 (13) |
C2B—N3B—C4B—C5B | 0.0 (7) | C11Z—N1Z—C2Z—O21Z | −5 (4) |
O41B—C4B—C5B—C6B | −179.9 (5) | C5Z—N1Z—C2Z—O21Z | −179 (2) |
N3B—C4B—C5B—C6B | 0.9 (8) | C11Z—N1Z—C2Z—C3Z | 178.4 (15) |
C4B—C5B—C6B—N61B | 178.8 (5) | C5Z—N1Z—C2Z—C3Z | 4 (3) |
C4B—C5B—C6B—N1B | −2.0 (8) | O21Z—C2Z—C3Z—C4Z | 177 (2) |
C2B—N1B—C6B—C5B | 2.2 (8) | N1Z—C2Z—C3Z—C4Z | −6 (3) |
C2B—N1B—C6B—N61B | −178.5 (5) | C2Z—C3Z—C4Z—C5Z | 6 (2) |
C5X—N1X—C2X—O21X | 178.9 (6) | C2Z—N1Z—C5Z—C4Z | 0 (3) |
C11X—N1X—C2X—O21X | 5.5 (11) | C11Z—N1Z—C5Z—C4Z | −174.6 (15) |
C5X—N1X—C2X—C3X | −1.5 (8) | C3Z—C4Z—C5Z—N1Z | −4 (3) |
C11X—N1X—C2X—C3X | −174.8 (6) | C2Z—O21Z—C2Z'—N1Z' | −2 (5) |
O21X—C2X—C3X—C4X | 171.9 (7) | C2Z—O21Z—C2Z'—C3Z' | −176 (15) |
N1X—C2X—C3X—C4X | −7.7 (8) | C1Z'—N1Z'—C2Z'—O21Z | 3 (8) |
C2X—C3X—C4X—C5X | 13.1 (7) | C5Z'—N1Z'—C2Z'—O21Z | −180 (6) |
C2X—N1X—C5X—C4X | 9.7 (8) | C1Z'—N1Z'—C2Z'—C3Z' | 178 (4) |
C11X—N1X—C5X—C4X | −176.8 (6) | C5Z'—N1Z'—C2Z'—C3Z' | −5 (6) |
C3X—C4X—C5X—N1X | −13.7 (7) | O21Z—C2Z'—C3Z'—C4Z' | −169 (5) |
C11Y—N1Y—C2Y—O21Y | −4 (3) | N1Z'—C2Z'—C3Z'—C4Z' | 15 (5) |
C5Y—N1Y—C2Y—O21Y | −174.7 (18) | C2Z'—C3Z'—C4Z'—C5Z' | −19 (4) |
C11Y—N1Y—C2Y—C3Y | 172.0 (14) | C2Z'—N1Z'—C5Z'—C4Z' | −7 (6) |
C5Y—N1Y—C2Y—C3Y | 1.0 (18) | C1Z'—N1Z'—C5Z'—C4Z' | 170 (4) |
O21Y—C2Y—C3Y—C4Y | −173.4 (17) | C3Z'—C4Z'—C5Z'—N1Z' | 16 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.88 | 1.94 | 2.760 (6) | 155 |
N3A—H3A···O41B | 0.88 | 1.85 | 2.724 (6) | 172 |
N61A—H61B···O21X | 0.88 | 2.14 | 2.912 (7) | 146 |
N61A—H61A···O41Bi | 0.88 | 1.98 | 2.847 (6) | 170 |
N1B—H1B···O21Z | 0.88 | 1.89 | 2.710 (7) | 154 |
N3B—H3B···O41A | 0.88 | 1.96 | 2.827 (6) | 171 |
N61B—H61D···O21Z | 0.88 | 2.08 | 2.844 (8) | 144 |
N61B—H61C···O2Y′ | 0.88 | 1.91 | 2.70 (2) | 149 |
N61B—H61C···O21Y | 0.88 | 2.21 | 2.985 (14) | 147 |
Symmetry code: (i) x+1/2, −y+1, z. |
2C4H5N3OS·3C5H9NO | F(000) = 2480 |
Mr = 583.74 | Dx = 1.332 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6864 reflections |
a = 7.5509 (7) Å | θ = 1.4–26.0° |
b = 15.2328 (12) Å | µ = 0.23 mm−1 |
c = 50.601 (3) Å | T = 173 K |
V = 5820.2 (8) Å3 | Plate, colourless |
Z = 8 | 0.29 × 0.14 × 0.10 mm |
Stoe IPDS II two-circle diffractometer | 5484 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 2211 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.157 |
ω scans | θmax = 25.7°, θmin = 1.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.936, Tmax = 0.977 | k = −18→16 |
30686 measured reflections | l = −59→61 |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.229 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2) + (0.1082P)2] where P = (Fo2 + 2Fc2)/3 |
5484 reflections | (Δ/σ)max < 0.001 |
367 parameters | Δρmax = 0.83 e Å−3 |
352 restraints | Δρmin = −0.43 e Å−3 |
2C4H5N3OS·3C5H9NO | V = 5820.2 (8) Å3 |
Mr = 583.74 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.5509 (7) Å | µ = 0.23 mm−1 |
b = 15.2328 (12) Å | T = 173 K |
c = 50.601 (3) Å | 0.29 × 0.14 × 0.10 mm |
Stoe IPDS II two-circle diffractometer | 5484 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 2211 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.977 | Rint = 0.157 |
30686 measured reflections |
R[F2 > 2σ(F2)] = 0.079 | 352 restraints |
wR(F2) = 0.229 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.83 e Å−3 |
5484 reflections | Δρmin = −0.43 e Å−3 |
367 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.2569 (6) | 0.0889 (3) | 0.06904 (9) | 0.0442 (11) | |
H1A | 0.2347 | 0.0766 | 0.0524 | 0.053* | |
C2A | 0.3391 (7) | 0.1662 (4) | 0.07474 (11) | 0.0437 (13) | |
S21A | 0.3865 (2) | 0.23898 (10) | 0.05127 (3) | 0.0581 (5) | |
N3A | 0.3761 (6) | 0.1785 (3) | 0.10057 (8) | 0.0412 (11) | |
H3A | 0.4309 | 0.2275 | 0.1047 | 0.049* | |
C4A | 0.3364 (7) | 0.1214 (4) | 0.12142 (11) | 0.0402 (13) | |
O41A | 0.3783 (5) | 0.1432 (3) | 0.14403 (7) | 0.0475 (10) | |
C5A | 0.2434 (7) | 0.0441 (4) | 0.11387 (11) | 0.0427 (13) | |
H5A | 0.2069 | 0.0032 | 0.1270 | 0.051* | |
C6A | 0.2067 (7) | 0.0286 (4) | 0.08798 (11) | 0.0405 (13) | |
N61A | 0.1208 (7) | −0.0419 (3) | 0.07876 (10) | 0.0532 (13) | |
H61A | 0.121 (8) | −0.049 (4) | 0.0615 (4) | 0.064* | |
H62A | 0.070 (7) | −0.080 (3) | 0.0895 (10) | 0.064* | |
N1B | 0.6753 (6) | 0.3964 (3) | 0.18927 (10) | 0.0481 (12) | |
H1B | 0.7069 | 0.4094 | 0.2055 | 0.058* | |
C2B | 0.6086 (7) | 0.3144 (4) | 0.18463 (11) | 0.0444 (13) | |
S21B | 0.5897 (2) | 0.23949 (11) | 0.20825 (3) | 0.0591 (5) | |
N3B | 0.5574 (5) | 0.2994 (3) | 0.15926 (8) | 0.0418 (11) | |
H3B | 0.5110 | 0.2478 | 0.1556 | 0.050* | |
C4B | 0.5732 (6) | 0.3600 (3) | 0.13848 (11) | 0.0398 (13) | |
O41B | 0.5208 (5) | 0.3362 (2) | 0.11592 (7) | 0.0426 (9) | |
C5B | 0.6468 (7) | 0.4416 (4) | 0.14502 (12) | 0.0448 (14) | |
H5B | 0.6621 | 0.4846 | 0.1316 | 0.054* | |
C6B | 0.6966 (7) | 0.4602 (4) | 0.17015 (12) | 0.0448 (14) | |
N61B | 0.7685 (7) | 0.5354 (3) | 0.17781 (11) | 0.0556 (13) | |
H61B | 0.759 (8) | 0.581 (3) | 0.1677 (11) | 0.067* | |
H62B | 0.790 (8) | 0.536 (4) | 0.1949 (5) | 0.067* | |
N1X | 0.2521 (7) | −0.0498 (4) | −0.01799 (10) | 0.0746 (16) | |
C11X | 0.2067 (11) | −0.1403 (5) | −0.01255 (16) | 0.091 (2) | |
H11A | 0.2092 | −0.1505 | 0.0066 | 0.137* | |
H11B | 0.2925 | −0.1791 | −0.0212 | 0.137* | |
H11C | 0.0877 | −0.1527 | −0.0193 | 0.137* | |
C2X | 0.2288 (9) | 0.0122 (4) | −0.00056 (12) | 0.0680 (17) | |
O21X | 0.1797 (6) | 0.0030 (3) | 0.02255 (8) | 0.0659 (12) | |
C3X | 0.2718 (10) | 0.1003 (5) | −0.01374 (14) | 0.087 (2) | |
H3X1 | 0.1634 | 0.1360 | −0.0160 | 0.105* | |
H3X2 | 0.3582 | 0.1340 | −0.0031 | 0.105* | |
C4X | 0.3486 (13) | 0.0760 (6) | −0.03980 (16) | 0.114 (3) | |
H4X1 | 0.4791 | 0.0822 | −0.0395 | 0.136* | |
H4X2 | 0.3005 | 0.1141 | −0.0539 | 0.136* | |
C5X | 0.2959 (10) | −0.0202 (5) | −0.04461 (12) | 0.086 (2) | |
H5X1 | 0.1925 | −0.0245 | −0.0566 | 0.104* | |
H5X2 | 0.3955 | −0.0543 | −0.0521 | 0.104* | |
N1Y | 0.5231 (9) | 0.7566 (5) | 0.14098 (19) | 0.122 (2) | |
C11Y | 0.4943 (15) | 0.7331 (9) | 0.1670 (2) | 0.154 (4) | |
H11D | 0.3666 | 0.7298 | 0.1704 | 0.232* | |
H11E | 0.5475 | 0.7770 | 0.1787 | 0.232* | |
H11F | 0.5482 | 0.6756 | 0.1704 | 0.232* | |
C2Y | 0.6165 (8) | 0.7070 (4) | 0.12516 (17) | 0.090 (2) | |
O21Y | 0.7036 (6) | 0.6421 (3) | 0.13124 (11) | 0.0805 (15) | |
C3Y | 0.6028 (9) | 0.7448 (4) | 0.09741 (17) | 0.118 (3) | |
H3Y1 | 0.5312 | 0.7068 | 0.0857 | 0.141* | |
H3Y2 | 0.7210 | 0.7542 | 0.0895 | 0.141* | |
C4Y | 0.5082 (12) | 0.8327 (5) | 0.1032 (2) | 0.128 (3) | |
H4Y1 | 0.5933 | 0.8817 | 0.1012 | 0.154* | |
H4Y2 | 0.4112 | 0.8415 | 0.0903 | 0.154* | |
C5Y | 0.4318 (9) | 0.8337 (5) | 0.1315 (2) | 0.134 (4) | |
H5Y1 | 0.4653 | 0.8873 | 0.1413 | 0.161* | |
H5Y2 | 0.3015 | 0.8265 | 0.1316 | 0.161* | |
N1Z | 0.8015 (9) | 0.5399 (5) | 0.27500 (11) | 0.0921 (19) | |
C11Z | 0.8688 (13) | 0.6228 (5) | 0.26735 (16) | 0.099 (3) | |
H11G | 0.9895 | 0.6297 | 0.2742 | 0.149* | |
H11H | 0.7932 | 0.6692 | 0.2746 | 0.149* | |
H11I | 0.8702 | 0.6268 | 0.2480 | 0.149* | |
C2Z | 0.7704 (8) | 0.4801 (5) | 0.25759 (12) | 0.0679 (18) | |
O21Z | 0.7883 (6) | 0.4842 (3) | 0.23342 (8) | 0.0663 (12) | |
C3Z | 0.7032 (10) | 0.3967 (5) | 0.27200 (14) | 0.095 (2) | |
H3Z1 | 0.5867 | 0.3779 | 0.2651 | 0.114* | |
H3Z2 | 0.7886 | 0.3477 | 0.2702 | 0.114* | |
C4Z | 0.6893 (12) | 0.4262 (7) | 0.29980 (16) | 0.126 (3) | |
H4Z1 | 0.7571 | 0.3860 | 0.3114 | 0.151* | |
H4Z2 | 0.5639 | 0.4253 | 0.3055 | 0.151* | |
C5Z | 0.7631 (10) | 0.5193 (6) | 0.30206 (11) | 0.093 (2) | |
H5Z1 | 0.6743 | 0.5601 | 0.3096 | 0.111* | |
H5Z2 | 0.8715 | 0.5208 | 0.3131 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.053 (3) | 0.040 (3) | 0.040 (3) | −0.004 (2) | −0.001 (2) | 0.001 (2) |
C2A | 0.046 (3) | 0.036 (3) | 0.049 (4) | 0.001 (2) | 0.003 (3) | 0.001 (3) |
S21A | 0.0850 (11) | 0.0438 (9) | 0.0457 (9) | −0.0086 (9) | 0.0079 (8) | 0.0058 (7) |
N3A | 0.047 (2) | 0.033 (2) | 0.044 (3) | −0.002 (2) | 0.005 (2) | −0.002 (2) |
C4A | 0.040 (3) | 0.041 (3) | 0.039 (3) | 0.001 (2) | 0.003 (2) | 0.003 (3) |
O41A | 0.054 (2) | 0.051 (2) | 0.038 (2) | −0.0054 (19) | 0.0027 (18) | 0.0009 (18) |
C5A | 0.045 (3) | 0.036 (3) | 0.046 (3) | −0.003 (3) | 0.004 (3) | 0.001 (3) |
C6A | 0.040 (3) | 0.037 (3) | 0.045 (3) | −0.003 (2) | 0.001 (2) | −0.004 (3) |
N61A | 0.065 (3) | 0.045 (3) | 0.050 (3) | −0.014 (3) | −0.002 (3) | 0.003 (3) |
N1B | 0.048 (3) | 0.051 (3) | 0.046 (3) | 0.008 (2) | −0.002 (2) | −0.005 (2) |
C2B | 0.043 (3) | 0.045 (4) | 0.045 (3) | 0.007 (3) | 0.005 (3) | −0.001 (3) |
S21B | 0.0776 (10) | 0.0545 (10) | 0.0452 (9) | 0.0033 (9) | 0.0018 (8) | 0.0046 (8) |
N3B | 0.045 (2) | 0.040 (3) | 0.040 (3) | −0.003 (2) | −0.001 (2) | −0.003 (2) |
C4B | 0.036 (3) | 0.037 (3) | 0.047 (3) | 0.006 (2) | 0.002 (2) | 0.001 (3) |
O41B | 0.053 (2) | 0.039 (2) | 0.035 (2) | −0.0019 (17) | −0.0012 (17) | −0.0010 (17) |
C5B | 0.047 (3) | 0.040 (3) | 0.048 (3) | 0.003 (3) | 0.002 (3) | 0.001 (3) |
C6B | 0.043 (3) | 0.038 (3) | 0.054 (4) | 0.005 (3) | −0.003 (3) | 0.002 (3) |
N61B | 0.070 (3) | 0.037 (3) | 0.059 (4) | 0.003 (3) | −0.015 (3) | −0.003 (3) |
N1X | 0.077 (4) | 0.097 (4) | 0.050 (3) | 0.012 (3) | 0.012 (3) | 0.008 (3) |
C11X | 0.115 (6) | 0.080 (5) | 0.079 (5) | 0.003 (5) | 0.010 (5) | −0.004 (4) |
C2X | 0.065 (4) | 0.086 (5) | 0.052 (4) | 0.005 (4) | 0.002 (3) | 0.001 (3) |
O21X | 0.090 (3) | 0.066 (3) | 0.042 (2) | −0.012 (2) | −0.001 (2) | −0.002 (2) |
C3X | 0.086 (5) | 0.095 (5) | 0.081 (5) | −0.001 (4) | −0.004 (4) | 0.026 (4) |
C4X | 0.117 (7) | 0.127 (7) | 0.097 (6) | 0.014 (6) | 0.020 (5) | 0.051 (5) |
C5X | 0.090 (5) | 0.122 (6) | 0.047 (4) | 0.034 (5) | 0.017 (4) | 0.019 (4) |
N1Y | 0.069 (4) | 0.069 (5) | 0.230 (7) | −0.005 (3) | −0.055 (5) | 0.007 (5) |
C11Y | 0.100 (7) | 0.161 (12) | 0.203 (9) | 0.022 (8) | 0.008 (9) | −0.014 (8) |
C2Y | 0.045 (4) | 0.046 (4) | 0.178 (7) | −0.014 (3) | −0.033 (4) | −0.018 (4) |
O21Y | 0.070 (3) | 0.050 (3) | 0.121 (4) | −0.002 (2) | −0.027 (3) | 0.009 (3) |
C3Y | 0.068 (4) | 0.051 (4) | 0.234 (7) | −0.026 (3) | −0.096 (5) | 0.054 (5) |
C4Y | 0.083 (6) | 0.081 (6) | 0.221 (9) | 0.005 (5) | −0.078 (6) | 0.012 (7) |
C5Y | 0.040 (4) | 0.064 (5) | 0.298 (11) | −0.001 (3) | −0.032 (6) | 0.028 (7) |
N1Z | 0.089 (4) | 0.128 (5) | 0.059 (4) | 0.030 (4) | −0.005 (3) | 0.000 (4) |
C11Z | 0.128 (7) | 0.096 (6) | 0.074 (5) | 0.004 (5) | −0.010 (5) | −0.005 (5) |
C2Z | 0.051 (4) | 0.094 (5) | 0.058 (4) | 0.020 (3) | −0.017 (3) | −0.018 (3) |
O21Z | 0.092 (3) | 0.064 (3) | 0.043 (2) | −0.002 (2) | −0.004 (2) | −0.006 (2) |
C3Z | 0.062 (4) | 0.155 (6) | 0.069 (5) | 0.035 (4) | 0.003 (4) | 0.037 (4) |
C4Z | 0.087 (6) | 0.188 (9) | 0.102 (6) | 0.031 (6) | 0.012 (5) | 0.042 (6) |
C5Z | 0.062 (4) | 0.178 (8) | 0.039 (3) | 0.045 (5) | −0.004 (3) | 0.002 (4) |
N1A—C2A | 1.363 (7) | C3X—H3X2 | 0.9900 |
N1A—C6A | 1.380 (7) | C4X—C5X | 1.537 (8) |
N1A—H1A | 0.8800 | C4X—H4X1 | 0.9900 |
C2A—N3A | 1.349 (7) | C4X—H4X2 | 0.9900 |
C2A—S21A | 1.663 (6) | C5X—H5X1 | 0.9900 |
N3A—C4A | 1.399 (7) | C5X—H5X2 | 0.9900 |
N3A—H3A | 0.8800 | N1Y—C2Y | 1.307 (7) |
C4A—O41A | 1.233 (6) | N1Y—C11Y | 1.381 (8) |
C4A—C5A | 1.424 (8) | N1Y—C5Y | 1.445 (7) |
C5A—C6A | 1.360 (8) | C11Y—H11D | 0.9800 |
C5A—H5A | 0.9500 | C11Y—H11E | 0.9800 |
C6A—N61A | 1.339 (7) | C11Y—H11F | 0.9800 |
N61A—H61A | 0.88 (2) | C2Y—O21Y | 1.227 (6) |
N61A—H62A | 0.88 (2) | C2Y—C3Y | 1.521 (8) |
N1B—C2B | 1.368 (7) | C3Y—C4Y | 1.546 (8) |
N1B—C6B | 1.381 (7) | C3Y—H3Y1 | 0.9900 |
N1B—H1B | 0.8800 | C3Y—H3Y2 | 0.9900 |
C2B—N3B | 1.360 (7) | C4Y—C5Y | 1.540 (8) |
C2B—S21B | 1.658 (6) | C4Y—H4Y1 | 0.9900 |
N3B—C4B | 1.404 (7) | C4Y—H4Y2 | 0.9900 |
N3B—H3B | 0.8800 | C5Y—H5Y1 | 0.9900 |
C4B—O41B | 1.262 (6) | C5Y—H5Y2 | 0.9900 |
C4B—C5B | 1.402 (8) | N1Z—C2Z | 1.289 (7) |
C5B—C6B | 1.356 (8) | N1Z—C11Z | 1.415 (7) |
C5B—H5B | 0.9500 | N1Z—C5Z | 1.435 (7) |
C6B—N61B | 1.325 (8) | C11Z—H11G | 0.9800 |
N61B—H61B | 0.87 (2) | C11Z—H11H | 0.9800 |
N61B—H62B | 0.88 (2) | C11Z—H11I | 0.9800 |
N1X—C2X | 1.305 (7) | C2Z—O21Z | 1.232 (6) |
N1X—C11X | 1.447 (7) | C2Z—C3Z | 1.549 (7) |
N1X—C5X | 1.459 (6) | C3Z—C4Z | 1.480 (8) |
C11X—H11A | 0.9800 | C3Z—H3Z1 | 0.9900 |
C11X—H11B | 0.9800 | C3Z—H3Z2 | 0.9900 |
C11X—H11C | 0.9800 | C4Z—C5Z | 1.528 (8) |
C2X—O21X | 1.235 (6) | C4Z—H4Z1 | 0.9900 |
C2X—C3X | 1.533 (7) | C4Z—H4Z2 | 0.9900 |
C3X—C4X | 1.487 (8) | C5Z—H5Z1 | 0.9900 |
C3X—H3X1 | 0.9900 | C5Z—H5Z2 | 0.9900 |
C2A—N1A—C6A | 123.6 (5) | N1X—C5X—C4X | 102.0 (6) |
C2A—N1A—H1A | 118.2 | N1X—C5X—H5X1 | 111.4 |
C6A—N1A—H1A | 118.2 | C4X—C5X—H5X1 | 111.4 |
N3A—C2A—N1A | 114.8 (5) | N1X—C5X—H5X2 | 111.4 |
N3A—C2A—S21A | 123.7 (4) | C4X—C5X—H5X2 | 111.4 |
N1A—C2A—S21A | 121.5 (4) | H5X1—C5X—H5X2 | 109.2 |
C2A—N3A—C4A | 126.9 (5) | C2Y—N1Y—C11Y | 121.2 (8) |
C2A—N3A—H3A | 116.6 | C2Y—N1Y—C5Y | 121.5 (8) |
C4A—N3A—H3A | 116.6 | C11Y—N1Y—C5Y | 117.0 (9) |
O41A—C4A—N3A | 118.6 (5) | N1Y—C11Y—H11D | 109.5 |
O41A—C4A—C5A | 126.7 (5) | N1Y—C11Y—H11E | 109.5 |
N3A—C4A—C5A | 114.7 (5) | H11D—C11Y—H11E | 109.5 |
C6A—C5A—C4A | 120.2 (5) | N1Y—C11Y—H11F | 109.5 |
C6A—C5A—H5A | 119.9 | H11D—C11Y—H11F | 109.5 |
C4A—C5A—H5A | 119.9 | H11E—C11Y—H11F | 109.5 |
N61A—C6A—C5A | 125.0 (5) | O21Y—C2Y—N1Y | 127.0 (8) |
N61A—C6A—N1A | 115.1 (5) | O21Y—C2Y—C3Y | 125.0 (7) |
C5A—C6A—N1A | 119.9 (5) | N1Y—C2Y—C3Y | 108.0 (7) |
C6A—N61A—H61A | 116 (4) | C2Y—C3Y—C4Y | 100.6 (7) |
C6A—N61A—H62A | 121 (4) | C2Y—C3Y—H3Y1 | 111.7 |
H61A—N61A—H62A | 122 (6) | C4Y—C3Y—H3Y1 | 111.7 |
C2B—N1B—C6B | 124.5 (5) | C2Y—C3Y—H3Y2 | 111.7 |
C2B—N1B—H1B | 117.8 | C4Y—C3Y—H3Y2 | 111.7 |
C6B—N1B—H1B | 117.8 | H3Y1—C3Y—H3Y2 | 109.4 |
N3B—C2B—N1B | 114.8 (5) | C5Y—C4Y—C3Y | 111.0 (7) |
N3B—C2B—S21B | 122.7 (4) | C5Y—C4Y—H4Y1 | 109.4 |
N1B—C2B—S21B | 122.4 (4) | C3Y—C4Y—H4Y1 | 109.4 |
C2B—N3B—C4B | 124.9 (5) | C5Y—C4Y—H4Y2 | 109.4 |
C2B—N3B—H3B | 117.5 | C3Y—C4Y—H4Y2 | 109.4 |
C4B—N3B—H3B | 117.5 | H4Y1—C4Y—H4Y2 | 108.0 |
O41B—C4B—C5B | 126.3 (5) | N1Y—C5Y—C4Y | 97.1 (7) |
O41B—C4B—N3B | 117.5 (5) | N1Y—C5Y—H5Y1 | 112.3 |
C5B—C4B—N3B | 116.1 (5) | C4Y—C5Y—H5Y1 | 112.3 |
C6B—C5B—C4B | 121.1 (5) | N1Y—C5Y—H5Y2 | 112.3 |
C6B—C5B—H5B | 119.4 | C4Y—C5Y—H5Y2 | 112.3 |
C4B—C5B—H5B | 119.4 | H5Y1—C5Y—H5Y2 | 109.9 |
N61B—C6B—C5B | 124.6 (6) | C2Z—N1Z—C11Z | 120.6 (6) |
N61B—C6B—N1B | 116.8 (5) | C2Z—N1Z—C5Z | 117.4 (7) |
C5B—C6B—N1B | 118.5 (5) | C11Z—N1Z—C5Z | 122.0 (7) |
C6B—N61B—H61B | 119 (4) | N1Z—C11Z—H11G | 109.5 |
C6B—N61B—H62B | 111 (4) | N1Z—C11Z—H11H | 109.5 |
H61B—N61B—H62B | 126 (6) | H11G—C11Z—H11H | 109.5 |
C2X—N1X—C11X | 122.0 (6) | N1Z—C11Z—H11I | 109.5 |
C2X—N1X—C5X | 115.5 (6) | H11G—C11Z—H11I | 109.5 |
C11X—N1X—C5X | 121.6 (6) | H11H—C11Z—H11I | 109.5 |
N1X—C11X—H11A | 109.5 | O21Z—C2Z—N1Z | 128.5 (7) |
N1X—C11X—H11B | 109.5 | O21Z—C2Z—C3Z | 123.0 (6) |
H11A—C11X—H11B | 109.5 | N1Z—C2Z—C3Z | 108.5 (6) |
N1X—C11X—H11C | 109.5 | C4Z—C3Z—C2Z | 102.8 (7) |
H11A—C11X—H11C | 109.5 | C4Z—C3Z—H3Z1 | 111.2 |
H11B—C11X—H11C | 109.5 | C2Z—C3Z—H3Z1 | 111.2 |
O21X—C2X—N1X | 126.8 (6) | C4Z—C3Z—H3Z2 | 111.2 |
O21X—C2X—C3X | 125.1 (6) | C2Z—C3Z—H3Z2 | 111.2 |
N1X—C2X—C3X | 108.1 (5) | H3Z1—C3Z—H3Z2 | 109.1 |
C4X—C3X—C2X | 104.5 (6) | C3Z—C4Z—C5Z | 109.1 (7) |
C4X—C3X—H3X1 | 110.9 | C3Z—C4Z—H4Z1 | 109.9 |
C2X—C3X—H3X1 | 110.9 | C5Z—C4Z—H4Z1 | 109.9 |
C4X—C3X—H3X2 | 110.9 | C3Z—C4Z—H4Z2 | 109.9 |
C2X—C3X—H3X2 | 110.9 | C5Z—C4Z—H4Z2 | 109.9 |
H3X1—C3X—H3X2 | 108.9 | H4Z1—C4Z—H4Z2 | 108.3 |
C3X—C4X—C5X | 106.1 (6) | N1Z—C5Z—C4Z | 101.9 (6) |
C3X—C4X—H4X1 | 110.5 | N1Z—C5Z—H5Z1 | 111.4 |
C5X—C4X—H4X1 | 110.5 | C4Z—C5Z—H5Z1 | 111.4 |
C3X—C4X—H4X2 | 110.5 | N1Z—C5Z—H5Z2 | 111.4 |
C5X—C4X—H4X2 | 110.5 | C4Z—C5Z—H5Z2 | 111.4 |
H4X1—C4X—H4X2 | 108.7 | H5Z1—C5Z—H5Z2 | 109.3 |
C6A—N1A—C2A—N3A | 3.0 (7) | C5X—N1X—C2X—C3X | −4.8 (9) |
C6A—N1A—C2A—S21A | −176.5 (4) | O21X—C2X—C3X—C4X | 172.1 (7) |
N1A—C2A—N3A—C4A | −1.1 (7) | N1X—C2X—C3X—C4X | −8.4 (8) |
S21A—C2A—N3A—C4A | 178.3 (4) | C2X—C3X—C4X—C5X | 17.1 (9) |
C2A—N3A—C4A—O41A | −179.3 (5) | C2X—N1X—C5X—C4X | 15.2 (9) |
C2A—N3A—C4A—C5A | −1.6 (7) | C11X—N1X—C5X—C4X | −175.3 (7) |
O41A—C4A—C5A—C6A | −179.8 (5) | C3X—C4X—C5X—N1X | −19.2 (9) |
N3A—C4A—C5A—C6A | 2.8 (7) | C11Y—N1Y—C2Y—O21Y | −8.5 (13) |
C4A—C5A—C6A—N61A | 179.8 (5) | C5Y—N1Y—C2Y—O21Y | 177.4 (7) |
C4A—C5A—C6A—N1A | −1.2 (8) | C11Y—N1Y—C2Y—C3Y | 172.7 (9) |
C2A—N1A—C6A—N61A | 177.2 (5) | C5Y—N1Y—C2Y—C3Y | −1.3 (9) |
C2A—N1A—C6A—C5A | −1.9 (8) | O21Y—C2Y—C3Y—C4Y | −169.9 (6) |
C6B—N1B—C2B—N3B | −1.9 (7) | N1Y—C2Y—C3Y—C4Y | 8.9 (7) |
C6B—N1B—C2B—S21B | 178.7 (4) | C2Y—C3Y—C4Y—C5Y | −13.5 (8) |
N1B—C2B—N3B—C4B | 1.7 (7) | C2Y—N1Y—C5Y—C4Y | −7.0 (9) |
S21B—C2B—N3B—C4B | −178.9 (4) | C11Y—N1Y—C5Y—C4Y | 178.8 (9) |
C2B—N3B—C4B—O41B | 179.5 (4) | C3Y—C4Y—C5Y—N1Y | 12.4 (9) |
C2B—N3B—C4B—C5B | −0.3 (7) | C11Z—N1Z—C2Z—O21Z | −1.5 (12) |
O41B—C4B—C5B—C6B | 179.2 (5) | C5Z—N1Z—C2Z—O21Z | 177.7 (6) |
N3B—C4B—C5B—C6B | −1.0 (7) | C11Z—N1Z—C2Z—C3Z | 178.5 (7) |
C4B—C5B—C6B—N61B | 179.3 (5) | C5Z—N1Z—C2Z—C3Z | −2.4 (8) |
C4B—C5B—C6B—N1B | 0.8 (8) | O21Z—C2Z—C3Z—C4Z | −175.1 (7) |
C2B—N1B—C6B—N61B | −177.9 (5) | N1Z—C2Z—C3Z—C4Z | 4.9 (8) |
C2B—N1B—C6B—C5B | 0.7 (8) | C2Z—C3Z—C4Z—C5Z | −5.6 (9) |
C11X—N1X—C2X—O21X | 5.4 (12) | C2Z—N1Z—C5Z—C4Z | −1.2 (9) |
C5X—N1X—C2X—O21X | 174.8 (7) | C11Z—N1Z—C5Z—C4Z | 178.0 (8) |
C11X—N1X—C2X—C3X | −174.1 (7) | C3Z—C4Z—C5Z—N1Z | 4.4 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O21Z | 0.88 | 1.91 | 2.740 (6) | 156 |
N3B—H3B···O41A | 0.88 | 1.97 | 2.843 (6) | 171 |
N61B—H61B···O21Y | 0.87 (2) | 2.11 (4) | 2.904 (7) | 152 (6) |
N61B—H62B···O21Z | 0.88 (2) | 2.10 (3) | 2.924 (7) | 155 (6) |
N1A—H1A···O21X | 0.88 | 1.92 | 2.753 (6) | 156 |
N3A—H3A···O41B | 0.88 | 1.88 | 2.751 (6) | 173 |
N61A—H61A···O21X | 0.88 (2) | 2.17 (4) | 2.959 (6) | 149 (6) |
N61A—H62A···O41Bi | 0.88 (2) | 1.97 (2) | 2.851 (6) | 174 (6) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Experimental details
(Ia) | (Ib) | (Ic) | (Id) | |
Crystal data | ||||
Chemical formula | C4H5N3OS·2C3H7NO | C4H5N3OS·C4H9NO | 2C4H5N3OS·3C4H9NO | 2C4H5N3OS·3C5H9NO |
Mr | 289.36 | 230.29 | 547.71 | 583.74 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n | Orthorhombic, Pca21 | Orthorhombic, Pca21 |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 8.0894 (16), 12.037 (3), 15.390 (3) | 9.4615 (9), 9.2679 (11), 13.4208 (12) | 15.2133 (7), 7.4335 (13), 24.445 (3) | 15.2293 (10), 7.5483 (4), 25.1871 (13) |
α, β, γ (°) | 89.774 (19), 89.466 (17), 76.691 (17) | 90, 101.801 (7), 90 | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 1458.2 (5) | 1152.0 (2) | 2764.4 (6) | 2895.4 (3) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.23 | 0.27 | 0.24 | 0.23 |
Crystal size (mm) | 0.30 × 0.15 × 0.10 | 0.50 × 0.30 × 0.25 | 0.27 × 0.20 × 0.15 | 0.34 × 0.28 × 0.16 |
Data collection | ||||
Diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) |
Tmin, Tmax | 0.933, 0.977 | 0.877, 0.936 | 0.938, 0.965 | 0.925, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11063, 5428, 1966 | 9565, 2163, 1968 | 33090, 5184, 3323 | 8280, 4332, 3541 |
Rint | 0.105 | 0.058 | 0.149 | 0.053 |
(sin θ/λ)max (Å−1) | 0.609 | 0.610 | 0.609 | 0.589 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.199, 0.90 | 0.040, 0.118, 1.07 | 0.063, 0.113, 0.93 | 0.062, 0.170, 1.06 |
No. of reflections | 5428 | 2163 | 5184 | 4332 |
No. of parameters | 351 | 171 | 378 | 474 |
No. of restraints | 0 | 132 | 357 | 569 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.40 | 0.24, −0.19 | 0.32, −0.23 | 0.36, −0.34 |
Absolute structure | ? | ? | Flack (1983), 2517 Friedel pairs | Flack (1983), 1810 Friedel pairs |
Absolute structure parameter | ? | ? | 0.04 (14) | 0.12 (15) |
(Ie) | |
Crystal data | |
Chemical formula | 2C4H5N3OS·3C5H9NO |
Mr | 583.74 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 173 |
a, b, c (Å) | 7.5509 (7), 15.2328 (12), 50.601 (3) |
α, β, γ (°) | 90, 90, 90 |
V (Å3) | 5820.2 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.29 × 0.14 × 0.10 |
Data collection | |
Diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001) |
Tmin, Tmax | 0.936, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30686, 5484, 2211 |
Rint | 0.157 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.229, 0.90 |
No. of reflections | 5484 |
No. of parameters | 367 |
No. of restraints | 352 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.83, −0.43 |
Absolute structure | ? |
Absolute structure parameter | ? |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O41B | 0.88 | 1.76 | 2.601 (7) | 160.0 |
N3A—H3A···O11X | 0.88 | 1.88 | 2.756 (7) | 170.4 |
N61A—H61A···O11W | 0.88 | 1.96 | 2.834 (9) | 171.8 |
N61A—H61B···O41B | 0.88 | 2.20 | 2.929 (8) | 140.2 |
N1B—H1B···O41Ai | 0.88 | 1.78 | 2.620 (7) | 158.6 |
N3B—H3B···O11Y | 0.88 | 1.87 | 2.738 (9) | 169.3 |
N61B—H61C···O11Z | 0.88 | 1.96 | 2.840 (8) | 173.7 |
N61B—H61D···O41Ai | 0.88 | 2.21 | 2.937 (7) | 140.1 |
Symmetry code: (i) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.883 (17) | 1.935 (19) | 2.743 (2) | 151 (2) |
N3A—H3A···O41Ai | 0.889 (16) | 1.902 (16) | 2.7892 (19) | 175 (2) |
N61A—H61A···O21X | 0.854 (17) | 2.08 (2) | 2.870 (2) | 153 (2) |
N61A—H62A···O41Aii | 0.875 (17) | 1.995 (18) | 2.848 (2) | 165 (2) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O21Z | 0.88 | 1.90 | 2.718 (6) | 154.9 |
N3B—H3B···O41A | 0.88 | 1.95 | 2.823 (5) | 172.9 |
N61B—H61B···O21Z | 0.879 (19) | 2.10 (4) | 2.873 (7) | 146 (5) |
N61B—H62B···O21Y | 0.869 (19) | 2.02 (3) | 2.830 (7) | 155 (6) |
N1A—H1A···O21X | 0.88 | 1.94 | 2.761 (6) | 155.7 |
N3A—H3A···O41B | 0.88 | 1.92 | 2.792 (5) | 172.3 |
N61A—H61A···O21X | 0.891 (19) | 2.18 (4) | 2.922 (6) | 140 (5) |
N61A—H62A···O41Bi | 0.87 (2) | 2.08 (2) | 2.937 (6) | 171 (5) |
Symmetry code: (i) x+1/2, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.88 | 1.94 | 2.760 (6) | 154.5 |
N3A—H3A···O41B | 0.88 | 1.85 | 2.724 (6) | 171.8 |
N61A—H61B···O21X | 0.88 | 2.14 | 2.912 (7) | 145.7 |
N61A—H61A···O41Bi | 0.88 | 1.98 | 2.847 (6) | 169.8 |
N1B—H1B···O21Z | 0.88 | 1.89 | 2.710 (7) | 153.6 |
N3B—H3B···O41A | 0.88 | 1.96 | 2.827 (6) | 170.6 |
N61B—H61D···O21Z | 0.88 | 2.08 | 2.844 (8) | 144.1 |
N61B—H61C···O2Y' | 0.88 | 1.91 | 2.70 (2) | 149.0 |
N61B—H61C···O21Y | 0.88 | 2.21 | 2.985 (14) | 146.9 |
Symmetry code: (i) x+1/2, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O21Z | 0.88 | 1.91 | 2.740 (6) | 155.6 |
N3B—H3B···O41A | 0.88 | 1.97 | 2.843 (6) | 170.7 |
N61B—H61B···O21Y | 0.87 (2) | 2.11 (4) | 2.904 (7) | 152 (6) |
N61B—H62B···O21Z | 0.88 (2) | 2.10 (3) | 2.924 (7) | 155 (6) |
N1A—H1A···O21X | 0.88 | 1.92 | 2.753 (6) | 156.3 |
N3A—H3A···O41B | 0.88 | 1.88 | 2.751 (6) | 172.6 |
N61A—H61A···O21X | 0.88 (2) | 2.17 (4) | 2.959 (6) | 149 (6) |
N61A—H62A···O41Bi | 0.88 (2) | 1.97 (2) | 2.851 (6) | 174 (6) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Crystal | 6-Amino-2-thiouracil monohydrate (mg, mmol) | Solvent | Temperature |
(Ia) | 5.8, 0.036 | DMF (270 µl) | Room temperature |
(Ib) | 7.3, 0.045 | DMF/DMAC (1:1 v/v, 75 µl) | Room temperature |
(Ic) | 4.5, 0.028 | DMAC (150 µl) | Room temperature |
(Id) | 4.4, 0.027 | NMP (50 µl) | Room temperature |
(Ie) | 6.3, 0.039 | NMP (110 µl) | 277 K |
Thioanalogues of the nucleobases play an important role in biological processes. For example, 2-thiouracil was found to be part of the anticodon of transfer RNAs. For six-membered cyclic compounds with hydrogen-bonding sites similar to 2-thiouracil, the R22(8) hydrogen-bonding pattern (Bernstein et al., 1995) turned out to be preferred for N—H···O or N—H···S interactions (Tutughamiarso & Egert, 2011). Moreover, a Cambridge Structural Database substructure search (CSD, Version 5.33, November 2011 plus four updates; Allen, 2002) revealed that for 2-thiouracil derivatives, N—H···S hydrogen bonds are solely observed within R22(8) motifs. Prompted by these results, we decided to crystallize 6-amino-2-thiouracil, (I), in order to analyse the effect of an additional NH2 donor group on the hydrogen-bonding pattern formed. 6-Amino-2-thiouracil shows anticorrosion and antifouling properties and can be used as an additive in marine anticorrosion paint (Tadros & Abd El Nabey, 2000). It exhibits antiviral activity (Romero et al., 1993) and is also an important precursor for the synthesis of compounds with various pharmacological properties, including anti-analgesic, anti-inflammatory (Alagarsamy et al., 2007; Youssif & Mohamed, 2008; Abu-Hashem & Youssef, 2011), antibacterial, antifungal, antitumour and diuretic activity (Mohamed et al., 2007; El-Gazzar & Hafez, 2009). Furthermore, it is used as a precursor for the synthesis of A3 adenosine receptor antagonists (Cosimelli et al., 2008), as well as for inhibitors of DNA III polymerase (Wright & Brown, 1976).
Crystallization experiments from different solvents yielded five new pseudopolymorphs of (I), i.e. the dimethylformamide (DMF) disolvate, (Ia), the dimethylacetamide (DMAC) monosolvate, (Ib), the dimethylacetamide sesquisolvate, (Ic), and two different 1-methylpyrrolidin-2-one (NMP) sesquisolvates, (Id and Ie).
Compound (Ia) crystallized in the triclinic space group P1 with two planar 6-amino-2-thiouracil molecules, A and B [r.m.s. deviations for all non-H atoms = 0.027 (A) and 0.024 Å (B)], and four DMF molecules, denoted W, X, Y, and Z, in the asymmetric unit (Fig. 1). All molecules in the asymmetric unit lie in a common plane parallel to (111) (r.m.s. deviation for all non-H atoms = 0.086 Å). The molecules of (I) are connected by N—H···O hydrogen bonds in an R21(6) pattern, forming chains running along [110] (Fig. 2). Linked by N—H···O hydrogen bonds to (I), the DMF molecules are located on both sides of the chains, respectively, with molecule A connected to the DMF molecules W and X and molecule B to DMF molecules Y and Z.
The DMAC solvate (Ib) crystallized in the monoclinic space group P21/n. The asymmetric unit consists of one 6-amino-2-thiouracil (r.m.s. deviation for all non-H atoms = 0.017 Å) and one disordered DMAC molecule. The two molecules are connected by an R21(6) pattern of N—H···O hydrogen bonds and are almost coplanar with each other (r.m.s. deviation = 0.088 Å for all non-H atoms; Fig. 3). In the crystal packing, the 6-amino-2-thiouracil molecules show R22(8) motifs of N—H···O hydrogen-bonded homodimers. Connected by further N—H···O hydrogen bonds, these dimers assemble to a three-dimensional network with adjacent dimers enclosing a dihedral angle of 48.26 (3)° (Fig. 4).
The two compounds (Ic) and (Id) are isomorphous and crystallized in the orthorhombic space group Pca21. The asymmetric unit consists of two 6-amino-2-thiouracil molecules, A and B [r.m.s. deviations for all non-H atoms = 0.024 (A) and 0.013 Å (B) in (Ic), and 0.022 (A) and 0.011 Å (B) in (Id)], and three solvent molecules, denoted X, Y and Z (Figs. 5 and 6). The DMAC molecules X and Y in (Ic), as well as the NMP molecules Y and Z in (Id), are disordered over two positions. The 6-amino-2-thiouracil molecules are connected to homodimers stabilized by an R22(8) pattern of N—H···O hydrogen bonds. Adjacent dimers are connected by further N—H···O hydrogen bonds and enclose a dihedral angle of 47.3 (1)° in (Ic) and 50.7 (7)° in (Id). In addition, the molecules of (I) show R21(6) N—H···O interactions with the solvent molecules whereby molecule A is connected to X and molecule B to Z, respectively (Fig. 7). Molecule B also forms an N—H···O hydrogen bond with solvent molecule Y. The crystal packing consists of zigzag-like chains of AB homodimers running along the a axis.
Pseudopolymorph (Ie) crystallized in the orthorhombic space group Pbca. The asymmetric unit consists of two 6-amino-2-thiouracil molecules, A and B [r.m.s. deviations for all non-H atoms = 0.020 (A) and 0.011 Å (B)], and three NMP molecules, denoted X, Y and Z (Fig. 8). The molecules of (I) form homodimers stabilized by R22(8) N—H···O hydrogen bonds. Adjacent dimers are connected by N—H···O hydrogen bonds and enclose a dihedral angle of 51.6 (6)°. Both molecules A and B show additional R21(6) N—H···O interactions with molecule A connected to molecule X and molecule B to Z, respectively (Fig. 9). Molecule B also forms one N—H···O hydrogen bond with the NMP molecule Y. In the crystal packing, the AB homodimers are arranged in a herringbone structure (Fig. 10).
In the structures of these five pseudopolymorphs, two different types of N—H···O hydrogen-bonding patterns are observed. In all structures, R21(6) motifs are present, which are either formed between two molecules of (I) in (Ia) or between one molecule of (I) and one solvent molecule in (Ib), (Ic), (Id) and (Ie), respectively. In the latter, four structures additional R22(8) patterns between molecules of (I) are formed. In these five structures, the S atoms do not participate in any hydrogen-bonding interactions.
The hydrogen-bonding pattern formed by (I) was compared with other 2-thiouracil derivatives retrieved from the CSD. This search yielded a total number of 39 hits whereby 29 structures contain R22(8) motifs. Nine of these structures show R22(8) motifs with two N—H···O hydrogen bonds [refcodes FAJWES (Brewer et al., 1987), FICBEY (Delage, H'Naifi & Goursolle, 1986), HEPMIY (Pastor et al., 1994), MUYTIK (Ivanova & Spiteller, 2010), HAFLAC (Antoniadis et al., 2003), LACJIJ (Tashkhodzhaev et al., 2002), EBAQOP (Balas et al., 2011), EBAQOP01 and DAYGUH (Kubicki et al., 2012)] and 11 structures contain R22(8) motifs characterized by two N—H···S hydrogen bonds [FALWOF (Orzeszko et al., 2004), FUWBOP (Medda et al., 2009), LOFDAL (Fonar et al., 1999), MUGMIK (Matković-Čalogović et al., 2002), PABNAJ, PABNIR (Chierotti et al., 2010), QAYCID (Van Hecke et al., 2005), QEHSEB (Tiekink, 2001), ZZZGEO01 (Delage, H'Naifi, Goursolle & Carpy 1986), CALFUS and CALGAZ (Tutughamiarso & Egert, 2011)]. In nine structures, two different R22(8) motifs with either two N—H···O or two N—H···S hydrogen bonds can be observed [CASPUI (Hu et al., 2005), GEMCAC (Read et al., 1988), PABPAL (Chierotti et al., 2010), RAPNAY (Long et al., 2005), TURCIL01 (Tiekink, 1989), TURCIL02 (Munshi & Row, 2006), UXIXUV (Ferreira et al., 2011), UXIXUV01 (Tutughamiarso & Egert, 2011) and LANZIL (Al-Deeb et al., 2012)].
The CSD search also yielded the crystal structure of the monohydrate of (I) [CSD refcodes AMTURM (Swaminathan & Chacko, 1978), AMTURM01 (Raper et al., 1985) and YEJKUV00 (Hützler & Bolte, 2012)], in which the molecules of (I) are connected by R21(6) motifs of N—H···O hydrogen bonds building chains that are cross-linked via the water molecules resulting in a three-dimensional network. Hydrogen bonds involving S atoms as an acceptor are only present between molecules of (I) and water (O—H···S).
In summary, the additional NH2 hydrogen-bond donor group at C6 (next to the N—H group) of 2-thiouracil seems to favour the formation of an R21(6) N—H···O hydrogen-bonding pattern since this motif is present in all crystal structures of (I). The S atom of (I) participates in hydrogen bonds exclusively in the presence of water which is the only incorporated solvent containing hydrogen bond donor groups. In four pseudopolymorphs of (I), the formation of R22(8) dimers is observed. This is in agreement with the results of a CSD substructure search, which revealed the R22(8) motif to be the most frequent hydrogen bonding pattern in crystal structures of 2-thiouracil derivatives.