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Since 6-amino­uracil derivatives show diversified use in various fields of application, we crystallized 6-amino­uracil to examine its preferred hydrogen-bonding frameworks. 6-Amino­uracil shows two rigid hydrogen-bonding sites, viz. one acceptor-donor-acceptor (ADA) site and one donor-donor-acceptor (DDA) site. During various crystallization attempts, we obtained three structures, namely two di­methyl­acetamide monosolvates, C4H5N3O2·C4H9NO, and a 1-methyl­pyrrolidin-2-one monosolvate, C4H5N3O2·C5H9NO. In all three structures, R21(6) N-H...O hydrogen-bonding patterns link the mol­ecules to their respective solvent mol­ecules. The formation of R22(8) N-H...O hydrogen-bond motifs between 6-amino­uracil mol­ecules can only be found in two-dimensional frameworks, whereas R33(14) N-H...O patterns are present when zigzag chzins of 6-amino­uracil mol­ecules are formed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113028874/uk3082sup1.cif
Contains datablocks Ia, Ib, Ic, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113028874/uk3082Iasup2.hkl
Contains datablock Ia

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113028874/uk3082Ibsup3.hkl
Contains datablock Ib

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113028874/uk3082Icsup4.hkl
Contains datablock Ic

CCDC references: 967600; 967601; 967602

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for (Ia), (Ib); SHELXL97 (Sheldrick, 2008 for (Ic). Molecular graphics: Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008) for (Ia); Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008) for (Ib), (Ic). For all compounds, software used to prepare material for publication: publCIF (Westrip, 2010).

(Ia) 6-Aminouracil dimethylacetamide monosolvate top
Crystal data top
C4H5N3O2·C4H9NOF(000) = 456
Mr = 214.23Dx = 1.382 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10028 reflections
a = 7.5434 (6) Åθ = 3.6–26.0°
b = 13.0020 (14) ŵ = 0.11 mm1
c = 10.5130 (9) ÅT = 173 K
β = 92.728 (7)°Block, colourless
V = 1029.94 (16) Å30.50 × 0.25 × 0.20 mm
Z = 4
Data collection top
Stoe IPDS II two-circle-
diffractometer
1934 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source1573 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.199
ω scansθmax = 25.7°, θmin = 3.6°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 99
Tmin = 0.948, Tmax = 0.979k = 1515
18537 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.089P)2 + 0.655P]
where P = (Fo2 + 2Fc2)/3
1934 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.43 e Å3
13 restraintsΔρmin = 0.36 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.3340 (3)0.46952 (14)0.3683 (2)0.0273 (5)
H10.294 (4)0.494 (2)0.439 (2)0.033*
C20.3373 (3)0.53561 (17)0.2676 (2)0.0267 (5)
O20.2784 (3)0.62310 (12)0.27295 (18)0.0357 (5)
N30.4094 (3)0.49673 (14)0.16167 (19)0.0275 (5)
H30.419 (4)0.5391 (18)0.098 (2)0.033*
C40.4785 (3)0.39847 (16)0.1506 (2)0.0253 (5)
O40.5416 (2)0.37412 (12)0.04642 (16)0.0316 (5)
C50.4726 (3)0.33477 (17)0.2577 (2)0.0261 (6)
H50.51610.26630.25460.031*
C60.4036 (3)0.37188 (16)0.3675 (2)0.0265 (5)
N60.3968 (3)0.32070 (16)0.4761 (2)0.0346 (6)
H610.350 (4)0.354 (3)0.545 (3)0.042*
H620.446 (4)0.261 (3)0.486 (3)0.042*
C1X0.1344 (4)0.4509 (3)0.8365 (3)0.0498 (8)
H1X10.08200.49690.89830.075*0.580 (10)
H1X20.25150.42820.86970.075*0.580 (10)
H1X30.05730.39100.82210.075*0.580 (10)
H4XA0.09800.45200.92480.075*0.420 (10)
H4XB0.26130.43510.83520.075*0.420 (10)
H4XC0.06650.39830.78860.075*0.420 (10)
O2X0.2133 (3)0.47928 (16)0.6096 (2)0.0482 (6)
C4X0.1023 (4)0.6645 (2)0.5923 (3)0.0430 (7)
H4X10.05110.73280.60510.064*0.580 (10)
H4X20.03630.62960.52230.064*0.580 (10)
H4X30.22690.67160.57140.064*0.580 (10)
H1XA0.05070.71080.65410.064*0.420 (10)
H1XB0.01740.65430.51990.064*0.420 (10)
H1XC0.21160.69480.56230.064*0.420 (10)
C5X0.0302 (4)0.6506 (3)0.8348 (3)0.0513 (8)
H5X10.01210.72070.81750.077*0.580 (10)
H5X20.12990.65260.89800.077*0.580 (10)
H5X30.06630.60940.86790.077*0.580 (10)
H5XA0.00210.63570.92300.077*0.420 (10)
H5XB0.07750.67340.78710.077*0.420 (10)
H5XC0.12010.70500.83390.077*0.420 (10)
C2X0.1531 (6)0.5070 (4)0.7135 (5)0.0321 (15)0.580 (10)
N3X0.0907 (6)0.6024 (4)0.7121 (5)0.0346 (14)0.580 (10)
C2X'0.1437 (8)0.5620 (4)0.6546 (6)0.0291 (19)0.420 (10)
N3X'0.0993 (7)0.5568 (4)0.7751 (5)0.0318 (19)0.420 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0346 (11)0.0191 (9)0.0286 (11)0.0017 (8)0.0048 (8)0.0003 (8)
C20.0304 (12)0.0165 (11)0.0328 (13)0.0009 (9)0.0013 (10)0.0001 (9)
O20.0469 (11)0.0184 (9)0.0423 (11)0.0052 (7)0.0061 (8)0.0012 (7)
N30.0376 (11)0.0180 (10)0.0265 (11)0.0002 (8)0.0008 (9)0.0029 (8)
C40.0305 (12)0.0169 (10)0.0283 (12)0.0024 (9)0.0011 (9)0.0024 (9)
O40.0487 (11)0.0198 (8)0.0265 (9)0.0003 (7)0.0053 (8)0.0010 (6)
C50.0347 (13)0.0162 (10)0.0274 (13)0.0002 (9)0.0003 (10)0.0009 (9)
C60.0304 (12)0.0176 (11)0.0312 (12)0.0004 (9)0.0003 (9)0.0023 (9)
N60.0513 (14)0.0236 (11)0.0295 (12)0.0080 (10)0.0083 (10)0.0043 (9)
C1X0.0539 (19)0.0540 (18)0.0411 (17)0.0214 (15)0.0026 (14)0.0134 (14)
O2X0.0555 (13)0.0488 (12)0.0413 (12)0.0021 (10)0.0125 (10)0.0153 (9)
C4X0.0497 (17)0.0327 (14)0.0461 (17)0.0003 (12)0.0026 (13)0.0050 (12)
C5X0.0460 (17)0.0515 (18)0.058 (2)0.0007 (14)0.0153 (15)0.0235 (15)
C2X0.031 (2)0.035 (3)0.031 (3)0.006 (2)0.003 (2)0.004 (2)
N3X0.037 (2)0.032 (3)0.035 (3)0.0038 (19)0.0029 (19)0.002 (2)
C2X'0.030 (3)0.027 (4)0.030 (4)0.000 (3)0.004 (3)0.008 (3)
N3X'0.038 (3)0.027 (3)0.031 (4)0.001 (2)0.010 (2)0.004 (3)
Geometric parameters (Å, º) top
N1—C21.364 (3)C1X—H4XC0.9799
N1—C61.374 (3)O2X—C2X1.256 (6)
N1—H10.875 (18)O2X—C2X'1.296 (6)
C2—O21.223 (3)C4X—N3X1.502 (6)
C2—N31.360 (3)C4X—C2X'1.512 (6)
N3—C41.387 (3)C4X—H4X10.9800
N3—H30.872 (14)C4X—H4X20.9800
C4—O41.256 (3)C4X—H4X30.9800
C4—C51.400 (3)C4X—H1XA0.9799
C5—C61.376 (3)C4X—H1XB0.9801
C5—H50.9500C4X—H1XC0.9799
C6—N61.325 (3)C5X—N3X'1.478 (5)
N6—H610.92 (3)C5X—N3X1.524 (6)
N6—H620.87 (3)C5X—H5X10.9800
C1X—C2X1.497 (6)C5X—H5X20.9800
C1X—N3X'1.538 (6)C5X—H5X30.9800
C1X—H1X10.9800C5X—H5XA0.9800
C1X—H1X20.9800C5X—H5XB0.9800
C1X—H1X30.9800C5X—H5XC0.9801
C1X—H4XA0.9800C2X—N3X1.326 (8)
C1X—H4XB0.9799C2X'—N3X'1.327 (8)
C2—N1—C6123.8 (2)N3X—C4X—H1XA74.6
C2—N1—H1116.8 (18)C2X'—C4X—H1XA109.6
C6—N1—H1119.1 (18)H4X2—C4X—H1XA125.4
O2—C2—N3122.9 (2)H4X3—C4X—H1XA120.4
O2—C2—N1122.0 (2)N3X—C4X—H1XB121.1
N3—C2—N1115.08 (19)C2X'—C4X—H1XB109.3
C2—N3—C4125.3 (2)H4X1—C4X—H1XB89.0
C2—N3—H3116.3 (19)H4X3—C4X—H1XB115.9
C4—N3—H3118.3 (19)H1XA—C4X—H1XB109.5
O4—C4—N3117.7 (2)N3X—C4X—H1XC124.7
O4—C4—C5125.5 (2)C2X'—C4X—H1XC109.5
N3—C4—C5116.8 (2)H4X1—C4X—H1XC91.3
C6—C5—C4119.7 (2)H4X2—C4X—H1XC110.4
C6—C5—H5120.2H1XA—C4X—H1XC109.5
C4—C5—H5120.2H1XB—C4X—H1XC109.5
N6—C6—N1115.3 (2)N3X'—C5X—H5X1143.8
N6—C6—C5125.4 (2)N3X—C5X—H5X1109.5
N1—C6—C5119.3 (2)N3X'—C5X—H5X292.0
C6—N6—H61118 (2)N3X—C5X—H5X2109.5
C6—N6—H62121 (2)H5X1—C5X—H5X2109.5
H61—N6—H62120 (3)N3X'—C5X—H5X389.0
C2X—C1X—H1X1109.5N3X—C5X—H5X3109.5
N3X'—C1X—H1X170.5H5X1—C5X—H5X3109.5
C2X—C1X—H1X2109.5H5X2—C5X—H5X3109.5
N3X'—C1X—H1X2123.6N3X'—C5X—H5XA109.6
H1X1—C1X—H1X2109.5N3X—C5X—H5XA143.8
C2X—C1X—H1X3109.5H5X1—C5X—H5XA106.1
N3X'—C1X—H1X3123.9H5X2—C5X—H5XA63.8
H1X1—C1X—H1X3109.5H5X3—C5X—H5XA50.1
H1X2—C1X—H1X3109.5N3X'—C5X—H5XB109.4
C2X—C1X—H4XA148.6N3X—C5X—H5XB88.0
N3X'—C1X—H4XA109.6H5X1—C5X—H5XB50.9
H1X2—C1X—H4XA87.4H5X2—C5X—H5XB158.4
H1X3—C1X—H4XA88.1H5X3—C5X—H5XB74.7
C2X—C1X—H4XB87.6H5XA—C5X—H5XB109.5
N3X'—C1X—H4XB109.3N3X'—C5X—H5XC109.4
H1X1—C1X—H4XB124.2N3X—C5X—H5XC93.0
H1X3—C1X—H4XB113.8H5X1—C5X—H5XC63.0
H4XA—C1X—H4XB109.5H5X2—C5X—H5XC58.5
C2X—C1X—H4XC87.9H5X3—C5X—H5XC157.4
N3X'—C1X—H4XC109.5H5XA—C5X—H5XC109.5
H1X1—C1X—H4XC123.4H5XB—C5X—H5XC109.5
H1X2—C1X—H4XC114.4O2X—C2X—N3X113.7 (5)
H4XA—C1X—H4XC109.5O2X—C2X—C1X131.7 (5)
H4XB—C1X—H4XC109.5N3X—C2X—C1X114.6 (5)
N3X—C4X—H4X1109.5C2X—N3X—C4X118.5 (5)
C2X'—C4X—H4X1144.5C2X—N3X—C5X119.7 (5)
N3X—C4X—H4X2109.5C4X—N3X—C5X121.4 (4)
C2X'—C4X—H4X290.3O2X—C2X'—N3X'115.6 (5)
H4X1—C4X—H4X2109.5O2X—C2X'—C4X130.7 (5)
N3X—C4X—H4X3109.5N3X'—C2X'—C4X113.7 (5)
C2X'—C4X—H4X390.0C2X'—N3X'—C5X118.3 (5)
H4X1—C4X—H4X3109.5C2X'—N3X'—C1X113.6 (5)
H4X2—C4X—H4X3109.5C5X—N3X'—C1X128.1 (4)
C6—N1—C2—O2177.9 (2)O2X—C2X—N3X—C5X174.0 (3)
C6—N1—C2—N32.5 (3)C1X—C2X—N3X—C5X7.7 (5)
O2—C2—N3—C4179.7 (2)C2X'—C4X—N3X—C2X0.5 (5)
N1—C2—N3—C40.7 (4)C2X'—C4X—N3X—C5X172.1 (6)
C2—N3—C4—O4179.6 (2)N3X'—C5X—N3X—C2X3.1 (4)
C2—N3—C4—C50.1 (3)N3X'—C5X—N3X—C4X175.7 (7)
O4—C4—C5—C6178.4 (2)C2X—O2X—C2X'—N3X'0.8 (4)
N3—C4—C5—C61.3 (3)C2X—O2X—C2X'—C4X178.5 (9)
C2—N1—C6—N6176.6 (2)N3X—C4X—C2X'—O2X177.5 (9)
C2—N1—C6—C53.7 (4)N3X—C4X—C2X'—N3X'1.8 (4)
C4—C5—C6—N6177.3 (2)O2X—C2X'—N3X'—C5X176.1 (4)
C4—C5—C6—N13.0 (4)C4X—C2X'—N3X'—C5X4.5 (7)
C2X'—O2X—C2X—N3X1.4 (4)O2X—C2X'—N3X'—C1X1.8 (7)
C2X'—O2X—C2X—C1X179.3 (8)C4X—C2X'—N3X'—C1X177.6 (4)
N3X'—C1X—C2X—O2X179.4 (7)N3X—C5X—N3X'—C2X'5.0 (4)
N3X'—C1X—C2X—N3X2.7 (4)N3X—C5X—N3X'—C1X177.4 (8)
O2X—C2X—N3X—C4X1.2 (6)C2X—C1X—N3X'—C2X'0.7 (4)
C1X—C2X—N3X—C4X179.5 (3)C2X—C1X—N3X'—C5X176.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2X0.88 (2)1.93 (2)2.738 (3)153 (3)
N3—H3···O4i0.87 (1)1.93 (2)2.796 (3)175 (3)
N6—H61···O2X0.92 (3)2.07 (3)2.885 (3)147 (3)
N6—H62···O4ii0.87 (3)1.99 (3)2.842 (3)168 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1/2, z+1/2.
(Ib) 6-Aminouracil dimethylacetamide monosolvate top
Crystal data top
C4H5N3O2·C4H9NOF(000) = 912
Mr = 214.23Dx = 1.390 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6388 reflections
a = 7.1200 (7) Åθ = 3.3–26.0°
b = 21.882 (3) ŵ = 0.11 mm1
c = 13.1561 (14) ÅT = 173 K
β = 92.908 (8)°Block, colourless
V = 2047.1 (4) Å30.30 × 0.25 × 0.20 mm
Z = 8
Data collection top
Stoe IPDS II two-circle
diffractometer
3823 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2098 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.062
ω scansθmax = 25.6°, θmin = 3.3°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 88
Tmin = 0.968, Tmax = 0.979k = 2625
11142 measured reflectionsl = 1513
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.085P)2]
where P = (Fo2 + 2Fc2)/3
3823 reflections(Δ/σ)max < 0.001
336 parametersΔρmax = 0.32 e Å3
23 restraintsΔρmin = 0.32 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.4153 (3)0.05272 (13)0.3919 (2)0.0249 (6)
H1A0.397 (5)0.0153 (18)0.381 (3)0.030*
C2A0.2669 (4)0.09028 (15)0.4043 (3)0.0244 (7)
O2A0.1051 (3)0.07105 (11)0.4039 (2)0.0344 (6)
N3A0.3101 (3)0.15044 (12)0.4166 (2)0.0253 (6)
H3A0.221 (4)0.1767 (13)0.421 (3)0.030*
C4A0.4902 (4)0.17479 (15)0.4155 (3)0.0252 (7)
O4A0.5049 (3)0.23125 (10)0.4273 (2)0.0341 (6)
C5A0.6367 (4)0.13355 (15)0.4005 (3)0.0251 (7)
H5A0.76240.14780.39810.030*
C6A0.5979 (4)0.07243 (15)0.3894 (3)0.0265 (8)
N6A0.7262 (4)0.02904 (14)0.3746 (3)0.0362 (8)
H61A0.844 (6)0.0431 (18)0.381 (3)0.043*
H62A0.691 (5)0.010 (2)0.371 (3)0.043*
N1B0.9085 (3)0.40713 (13)0.3952 (2)0.0253 (6)
H1B0.885 (5)0.4453 (18)0.383 (3)0.030*
C2B0.7615 (4)0.36816 (15)0.4083 (3)0.0232 (7)
O2B0.5996 (3)0.38757 (10)0.4116 (2)0.0328 (6)
N3B0.8062 (3)0.30841 (12)0.4175 (2)0.0252 (7)
H3B0.715 (4)0.2810 (13)0.423 (3)0.030*
C4B0.9882 (4)0.28439 (15)0.4146 (3)0.0255 (8)
O4B1.0040 (3)0.22820 (10)0.4231 (2)0.0370 (7)
C5B1.1326 (4)0.32690 (15)0.4014 (3)0.0263 (8)
H5B1.25930.31340.39970.032*
C6B1.0916 (4)0.38732 (15)0.3909 (3)0.0235 (7)
N6B1.2174 (4)0.43128 (14)0.3744 (3)0.0328 (7)
H61B1.334 (6)0.4205 (18)0.371 (3)0.039*
H62B1.190 (5)0.4687 (19)0.363 (3)0.039*
C1X1.0261 (5)0.63621 (18)0.3249 (3)0.0432 (10)
H11X0.95540.67460.32030.065*0.734 (10)
H12X1.08430.62850.26020.065*0.734 (10)
H13X1.12420.63920.37970.065*0.734 (10)
H4AX1.06950.66620.37620.065*0.266 (10)
H4BX1.03800.65340.25680.065*0.266 (10)
H4CX1.10290.59910.33210.065*0.266 (10)
O2X0.9428 (4)0.52995 (12)0.3574 (2)0.0463 (7)
C4X0.5815 (5)0.54814 (19)0.3741 (3)0.0451 (10)
H41X0.45410.56480.37650.068*0.734 (10)
H42X0.61760.52890.43940.068*0.734 (10)
H43X0.58470.51760.31970.068*0.734 (10)
H1AX0.56460.50450.38750.068*0.266 (10)
H1BX0.50590.55970.31280.068*0.266 (10)
H1CX0.54110.57190.43220.068*0.266 (10)
N3X0.7104 (5)0.59645 (17)0.3544 (3)0.0305 (13)0.734 (10)
C2X0.8918 (6)0.5834 (2)0.3477 (4)0.0272 (13)0.734 (10)
C5X0.6305 (8)0.6582 (2)0.3530 (4)0.0351 (14)0.734 (10)
H51X0.49400.65560.35880.053*0.734 (10)
H52X0.65790.67840.28900.053*0.734 (10)
H53X0.68610.68170.41040.053*0.734 (10)
N3X'0.8343 (18)0.6214 (7)0.3389 (12)0.062 (5)*0.266 (10)
C2X'0.7903 (8)0.5611 (4)0.3579 (15)0.061 (6)*0.266 (10)
C5X'0.715 (3)0.6753 (8)0.3421 (14)0.051 (5)*0.266 (10)
H5AX0.78680.71150.32410.077*0.266 (10)
H5BX0.66970.68020.41080.077*0.266 (10)
H5CX0.60690.67040.29340.077*0.266 (10)
C1Y0.5534 (5)0.17677 (18)0.3162 (3)0.0424 (10)
H11Y0.48690.21590.31140.064*0.582 (12)
H12Y0.65160.17870.37100.064*0.582 (12)
H13Y0.61100.16820.25150.064*0.582 (12)
H4AY0.60450.20610.36670.064*0.418 (12)
H4BY0.62360.13830.32260.064*0.418 (12)
H4CY0.56510.19350.24770.064*0.418 (12)
O2Y0.4495 (4)0.06969 (12)0.3494 (2)0.0471 (7)
C4Y0.1021 (5)0.0940 (2)0.3677 (3)0.0452 (10)
H41Y0.02430.11170.36850.068*0.582 (12)
H42Y0.10320.06150.31660.068*0.582 (12)
H43Y0.13730.07710.43500.068*0.582 (12)
H1AY0.02850.10450.30520.068*0.418 (12)
H1BY0.08490.05060.38320.068*0.418 (12)
H1CY0.05950.11890.42410.068*0.418 (12)
N3Y0.2337 (9)0.1406 (3)0.3431 (4)0.033 (2)0.582 (12)
C2Y0.4136 (10)0.1256 (4)0.3388 (5)0.030 (2)0.582 (12)
C5Y0.1674 (15)0.2047 (6)0.3453 (13)0.044 (3)0.582 (12)
H51Y0.03100.20530.35220.067*0.582 (12)
H52Y0.22970.22590.40330.067*0.582 (12)
H53Y0.19770.22520.28200.067*0.582 (12)
N3Y'0.3572 (12)0.1656 (4)0.3332 (5)0.032 (3)0.418 (12)
C2Y'0.3110 (7)0.1067 (3)0.3532 (8)0.035 (3)0.418 (12)
C5Y'0.239 (2)0.2184 (8)0.3394 (15)0.042 (4)0.418 (12)
H5AY0.27750.24920.29050.063*0.418 (12)
H5BY0.10810.20670.32350.063*0.418 (12)
H5CY0.25120.23530.40840.063*0.418 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0197 (12)0.0203 (15)0.0345 (17)0.0020 (11)0.0000 (11)0.0014 (13)
C2A0.0198 (14)0.0256 (18)0.0278 (19)0.0047 (13)0.0000 (13)0.0007 (15)
O2A0.0180 (10)0.0317 (14)0.0536 (17)0.0049 (10)0.0031 (10)0.0028 (12)
N3A0.0167 (12)0.0222 (15)0.0369 (17)0.0020 (11)0.0006 (11)0.0003 (13)
C4A0.0198 (14)0.0247 (19)0.0311 (19)0.0036 (13)0.0017 (13)0.0034 (15)
O4A0.0221 (11)0.0217 (14)0.0587 (17)0.0026 (9)0.0040 (11)0.0011 (12)
C5A0.0175 (13)0.0228 (17)0.035 (2)0.0018 (13)0.0012 (13)0.0004 (15)
C6A0.0183 (14)0.0301 (19)0.031 (2)0.0017 (13)0.0009 (13)0.0018 (15)
N6A0.0174 (13)0.0257 (17)0.066 (2)0.0017 (12)0.0028 (13)0.0041 (16)
N1B0.0207 (12)0.0183 (14)0.0368 (18)0.0040 (11)0.0016 (11)0.0011 (13)
C2B0.0193 (14)0.0239 (18)0.0265 (19)0.0003 (13)0.0015 (12)0.0020 (14)
O2B0.0190 (10)0.0294 (13)0.0502 (17)0.0048 (10)0.0032 (10)0.0022 (12)
N3B0.0158 (12)0.0235 (16)0.0366 (18)0.0005 (11)0.0039 (11)0.0013 (13)
C4B0.0210 (14)0.0228 (19)0.033 (2)0.0040 (13)0.0013 (13)0.0003 (15)
O4B0.0243 (11)0.0222 (14)0.0649 (19)0.0023 (10)0.0065 (11)0.0041 (12)
C5B0.0175 (14)0.0272 (19)0.034 (2)0.0040 (13)0.0014 (13)0.0012 (15)
C6B0.0151 (13)0.0292 (18)0.0261 (19)0.0023 (13)0.0015 (12)0.0012 (15)
N6B0.0181 (13)0.0231 (16)0.057 (2)0.0021 (12)0.0029 (13)0.0049 (15)
C1X0.048 (2)0.033 (2)0.049 (3)0.0074 (17)0.0014 (18)0.0013 (18)
O2X0.0461 (15)0.0307 (16)0.062 (2)0.0087 (12)0.0020 (13)0.0030 (14)
C4X0.0326 (18)0.051 (3)0.052 (3)0.0010 (18)0.0079 (17)0.000 (2)
N3X0.032 (2)0.023 (2)0.036 (3)0.0005 (17)0.0029 (17)0.0033 (18)
C2X0.039 (3)0.015 (3)0.028 (3)0.003 (2)0.002 (2)0.003 (2)
C5X0.036 (3)0.026 (3)0.043 (3)0.007 (2)0.002 (2)0.002 (2)
C1Y0.0404 (19)0.035 (2)0.053 (3)0.0059 (17)0.0086 (18)0.0030 (19)
O2Y0.0565 (17)0.0223 (15)0.062 (2)0.0104 (12)0.0002 (14)0.0036 (13)
C4Y0.0336 (19)0.057 (3)0.045 (3)0.0005 (18)0.0070 (17)0.009 (2)
N3Y0.036 (4)0.030 (4)0.034 (3)0.001 (3)0.005 (2)0.002 (3)
C2Y0.033 (4)0.027 (5)0.030 (4)0.001 (3)0.003 (3)0.002 (3)
C5Y0.046 (6)0.041 (6)0.046 (6)0.026 (5)0.005 (6)0.002 (5)
N3Y'0.047 (6)0.018 (5)0.032 (4)0.009 (4)0.006 (3)0.003 (3)
C2Y'0.036 (6)0.028 (7)0.043 (6)0.005 (5)0.003 (4)0.003 (4)
C5Y'0.054 (10)0.038 (9)0.033 (6)0.025 (7)0.001 (8)0.010 (6)
Geometric parameters (Å, º) top
N1A—C2A1.355 (4)C4X—H43X0.9800
N1A—C6A1.372 (4)C4X—H1AX0.9800
N1A—H1A0.84 (4)C4X—H1BX0.9800
C2A—O2A1.226 (4)C4X—H1CX0.9800
C2A—N3A1.360 (4)N3X—C2X1.330 (6)
N3A—C4A1.389 (4)N3X—C5X1.465 (6)
N3A—H3A0.862 (18)C5X—H51X0.9800
C4A—O4A1.249 (4)C5X—H52X0.9800
C4A—C5A1.401 (4)C5X—H53X0.9800
C5A—C6A1.372 (5)N3X'—C2X'1.382 (14)
C5A—H5A0.9500N3X'—C5X'1.46 (2)
C6A—N6A1.339 (4)C5X'—H5AX0.9800
N6A—H61A0.89 (4)C5X'—H5BX0.9800
N6A—H62A0.89 (4)C5X'—H5CX0.9800
N1B—C2B1.368 (4)C1Y—N3Y'1.447 (9)
N1B—C6B1.377 (4)C1Y—C2Y1.537 (8)
N1B—H1B0.86 (4)C1Y—H11Y0.9800
C2B—O2B1.231 (4)C1Y—H12Y0.9800
C2B—N3B1.350 (4)C1Y—H13Y0.9800
N3B—C4B1.401 (4)C1Y—H4AY0.9800
N3B—H3B0.888 (18)C1Y—H4BY0.9800
C4B—O4B1.239 (4)C1Y—H4CY0.9800
C4B—C5B1.404 (4)O2Y—C2Y1.256 (8)
C5B—C6B1.360 (5)O2Y—C2Y'1.279 (5)
C5B—H5B0.9500C4Y—N3Y1.433 (7)
C6B—N6B1.340 (4)C4Y—C2Y'1.535 (5)
N6B—H61B0.87 (4)C4Y—H41Y0.9800
N6B—H62B0.85 (4)C4Y—H42Y0.9800
C1X—N3X'1.425 (13)C4Y—H43Y0.9800
C1X—C2X1.539 (6)C4Y—H1AY0.9800
C1X—H11X0.9800C4Y—H1BY0.9800
C1X—H12X0.9800C4Y—H1CY0.9800
C1X—H13X0.9800N3Y—C2Y1.326 (10)
C1X—H4AX0.9800N3Y—C5Y1.480 (15)
C1X—H4BX0.9800C5Y—H51Y0.9800
C1X—H4CX0.9800C5Y—H52Y0.9800
O2X—C2X1.230 (5)C5Y—H53Y0.9800
O2X—C2X'1.283 (5)N3Y'—C2Y'1.359 (11)
C4X—N3X1.432 (5)N3Y'—C5Y'1.433 (19)
C4X—C2X'1.539 (5)C5Y'—H5AY0.9800
C4X—H41X0.9800C5Y'—H5BY0.9800
C4X—H42X0.9800C5Y'—H5CY0.9800
C2A—N1A—C6A123.9 (3)O2X—C2X—N3X118.6 (4)
C2A—N1A—H1A120 (2)O2X—C2X—C1X123.5 (4)
C6A—N1A—H1A116 (2)N3X—C2X—C1X117.9 (4)
O2A—C2A—N1A122.0 (3)N3X—C5X—H51X109.5
O2A—C2A—N3A122.7 (3)N3X—C5X—H52X109.5
N1A—C2A—N3A115.4 (3)H51X—C5X—H52X109.5
C2A—N3A—C4A125.0 (3)N3X—C5X—H53X109.5
C2A—N3A—H3A119 (2)H51X—C5X—H53X109.5
C4A—N3A—H3A116 (2)H52X—C5X—H53X109.5
O4A—C4A—N3A116.7 (3)C2X'—N3X'—C1X117.9 (10)
O4A—C4A—C5A126.6 (3)C2X'—N3X'—C5X'129.0 (12)
N3A—C4A—C5A116.7 (3)C1X—N3X'—C5X'112.7 (12)
C6A—C5A—C4A119.7 (3)O2X—C2X'—N3X'107.9 (8)
C6A—C5A—H5A120.1O2X—C2X'—C4X136.6 (8)
C4A—C5A—H5A120.1N3X'—C2X'—C4X115.5 (7)
N6A—C6A—N1A115.8 (3)N3X'—C5X'—H5AX109.5
N6A—C6A—C5A124.9 (3)N3X'—C5X'—H5BX109.5
N1A—C6A—C5A119.3 (3)H5AX—C5X'—H5BX109.5
C6A—N6A—H61A113 (3)N3X'—C5X'—H5CX109.5
C6A—N6A—H62A120 (2)H5AX—C5X'—H5CX109.5
H61A—N6A—H62A126 (4)H5BX—C5X'—H5CX109.5
C2B—N1B—C6B122.7 (3)N3Y'—C1Y—H11Y71.9
C2B—N1B—H1B119 (2)C2Y—C1Y—H11Y109.5
C6B—N1B—H1B118 (2)N3Y'—C1Y—H12Y123.4
O2B—C2B—N3B123.2 (3)C2Y—C1Y—H12Y109.5
O2B—C2B—N1B120.9 (3)H11Y—C1Y—H12Y109.5
N3B—C2B—N1B115.9 (3)N3Y'—C1Y—H13Y123.5
C2B—N3B—C4B125.1 (3)C2Y—C1Y—H13Y109.5
C2B—N3B—H3B120 (2)H11Y—C1Y—H13Y109.5
C4B—N3B—H3B115 (2)H12Y—C1Y—H13Y109.5
O4B—C4B—N3B116.7 (3)N3Y'—C1Y—H4AY109.5
O4B—C4B—C5B127.2 (3)C2Y—C1Y—H4AY124.5
N3B—C4B—C5B116.1 (3)H11Y—C1Y—H4AY68.4
C6B—C5B—C4B120.1 (3)H13Y—C1Y—H4AY123.7
C6B—C5B—H5B119.9N3Y'—C1Y—H4BY109.5
C4B—C5B—H5B119.9C2Y—C1Y—H4BY71.9
N6B—C6B—C5B124.9 (3)H11Y—C1Y—H4BY177.9
N6B—C6B—N1B115.0 (3)H12Y—C1Y—H4BY68.4
C5B—C6B—N1B120.1 (3)H13Y—C1Y—H4BY71.2
C6B—N6B—H61B118 (3)H4AY—C1Y—H4BY109.5
C6B—N6B—H62B125 (3)N3Y'—C1Y—H4CY109.5
H61B—N6B—H62B118 (4)C2Y—C1Y—H4CY122.4
N3X'—C1X—H11X73.1H11Y—C1Y—H4CY71.2
C2X—C1X—H11X109.5H12Y—C1Y—H4CY124.8
N3X'—C1X—H12X121.5H4AY—C1Y—H4CY109.5
C2X—C1X—H12X109.5H4BY—C1Y—H4CY109.5
H11X—C1X—H12X109.5N3Y—C4Y—H41Y109.5
N3X'—C1X—H13X124.9C2Y'—C4Y—H41Y145.7
C2X—C1X—H13X109.5N3Y—C4Y—H42Y109.5
H11X—C1X—H13X109.5C2Y'—C4Y—H42Y90.2
H12X—C1X—H13X109.5H41Y—C4Y—H42Y109.5
N3X'—C1X—H4AX109.5N3Y—C4Y—H43Y109.5
C2X—C1X—H4AX123.1C2Y'—C4Y—H43Y88.6
H11X—C1X—H4AX67.1H41Y—C4Y—H43Y109.5
H12X—C1X—H4AX125.6H42Y—C4Y—H43Y109.5
N3X'—C1X—H4BX109.5N3Y—C4Y—H1AY88.4
C2X—C1X—H4BX123.4C2Y'—C4Y—H1AY109.5
H11X—C1X—H4BX71.4H41Y—C4Y—H1AY57.6
H13X—C1X—H4BX123.8H42Y—C4Y—H1AY67.4
H4AX—C1X—H4BX109.5H43Y—C4Y—H1AY161.4
N3X'—C1X—H4CX109.5N3Y—C4Y—H1BY145.7
C2X—C1X—H4CX73.1C2Y'—C4Y—H1BY109.5
H11X—C1X—H4CX176.4H41Y—C4Y—H1BY104.8
H12X—C1X—H4CX71.5H42Y—C4Y—H1BY56.2
H13X—C1X—H4CX67.1H43Y—C4Y—H1BY58.3
H4AX—C1X—H4CX109.5H1AY—C4Y—H1BY109.5
H4BX—C1X—H4CX109.5N3Y—C4Y—H1CY90.5
N3X—C4X—H41X109.5C2Y'—C4Y—H1CY109.5
C2X'—C4X—H41X146.9H41Y—C4Y—H1CY56.9
N3X—C4X—H42X109.5H42Y—C4Y—H1CY159.4
C2X'—C4X—H42X89.3H43Y—C4Y—H1CY66.5
H41X—C4X—H42X109.5H1AY—C4Y—H1CY109.5
N3X—C4X—H43X109.5H1BY—C4Y—H1CY109.5
C2X'—C4X—H43X88.1C2Y—N3Y—C4Y118.6 (6)
H41X—C4X—H43X109.5C2Y—N3Y—C5Y123.0 (7)
H42X—C4X—H43X109.5C4Y—N3Y—C5Y117.2 (6)
N3X—C4X—H1AX146.9O2Y—C2Y—N3Y115.3 (6)
C2X'—C4X—H1AX109.5O2Y—C2Y—C1Y126.9 (6)
H41X—C4X—H1AX103.6N3Y—C2Y—C1Y117.7 (7)
H42X—C4X—H1AX56.8N3Y—C5Y—H51Y109.5
H43X—C4X—H1AX58.3N3Y—C5Y—H52Y109.5
N3X—C4X—H1BX89.5H51Y—C5Y—H52Y109.5
C2X'—C4X—H1BX109.5N3Y—C5Y—H53Y109.5
H41X—C4X—H1BX57.2H51Y—C5Y—H53Y109.5
H42X—C4X—H1BX160.4H52Y—C5Y—H53Y109.5
H43X—C4X—H1BX66.9C2Y'—N3Y'—C5Y'127.2 (9)
H1AX—C4X—H1BX109.5C2Y'—N3Y'—C1Y115.8 (7)
N3X—C4X—H1CX88.0C5Y'—N3Y'—C1Y116.5 (8)
C2X'—C4X—H1CX109.5O2Y—C2Y'—N3Y'113.5 (6)
H41X—C4X—H1CX57.9O2Y—C2Y'—C4Y130.1 (6)
H42X—C4X—H1CX67.5N3Y'—C2Y'—C4Y116.2 (6)
H43X—C4X—H1CX161.8N3Y'—C5Y'—H5AY109.5
H1AX—C4X—H1CX109.5N3Y'—C5Y'—H5BY109.5
H1BX—C4X—H1CX109.5H5AY—C5Y'—H5BY109.5
C2X—N3X—C4X119.2 (4)N3Y'—C5Y'—H5CY109.5
C2X—N3X—C5X125.1 (4)H5AY—C5Y'—H5CY109.5
C4X—N3X—C5X115.5 (4)H5BY—C5Y'—H5CY109.5
C6A—N1A—C2A—O2A178.3 (3)N3X'—C1X—C2X—O2X177.1 (14)
C6A—N1A—C2A—N3A1.4 (5)N3X'—C1X—C2X—N3X1.1 (11)
O2A—C2A—N3A—C4A178.6 (3)C2X—C1X—N3X'—C2X'1.0 (11)
N1A—C2A—N3A—C4A1.1 (5)C2X—C1X—N3X'—C5X'172 (2)
C2A—N3A—C4A—O4A179.5 (3)C2X—O2X—C2X'—N3X'1.6 (8)
C2A—N3A—C4A—C5A0.0 (5)C2X—O2X—C2X'—C4X178 (3)
O4A—C4A—C5A—C6A179.6 (4)C1X—N3X'—C2X'—O2X1 (2)
N3A—C4A—C5A—C6A0.9 (5)C5X'—N3X'—C2X'—O2X173.0 (17)
C2A—N1A—C6A—N6A178.8 (3)C1X—N3X'—C2X'—C4X179.1 (12)
C2A—N1A—C6A—C5A0.5 (5)C5X'—N3X'—C2X'—C4X7 (3)
C4A—C5A—C6A—N6A179.9 (4)N3X—C4X—C2X'—O2X179 (3)
C4A—C5A—C6A—N1A0.7 (5)N3X—C4X—C2X'—N3X'1.0 (9)
C6B—N1B—C2B—O2B179.9 (3)C2Y'—C4Y—N3Y—C2Y1.3 (7)
C6B—N1B—C2B—N3B0.3 (5)C2Y'—C4Y—N3Y—C5Y166.1 (12)
O2B—C2B—N3B—C4B179.7 (3)C2Y'—O2Y—C2Y—N3Y5.4 (8)
N1B—C2B—N3B—C4B0.1 (5)C2Y'—O2Y—C2Y—C1Y178.1 (12)
C2B—N3B—C4B—O4B179.2 (3)C4Y—N3Y—C2Y—O2Y5.4 (8)
C2B—N3B—C4B—C5B0.2 (5)C5Y—N3Y—C2Y—O2Y172.0 (9)
O4B—C4B—C5B—C6B178.5 (4)C4Y—N3Y—C2Y—C1Y177.8 (5)
N3B—C4B—C5B—C6B0.8 (5)C5Y—N3Y—C2Y—C1Y11.2 (11)
C4B—C5B—C6B—N6B177.6 (3)N3Y'—C1Y—C2Y—O2Y179.7 (10)
C4B—C5B—C6B—N1B1.2 (5)N3Y'—C1Y—C2Y—N3Y3.3 (6)
C2B—N1B—C6B—N6B177.9 (3)C2Y—C1Y—N3Y'—C2Y'1.4 (7)
C2B—N1B—C6B—C5B1.0 (5)C2Y—C1Y—N3Y'—C5Y'174.0 (13)
C2X'—C4X—N3X—C2X0.9 (13)C2Y—O2Y—C2Y'—N3Y'0.6 (6)
C2X'—C4X—N3X—C5X175.3 (14)C2Y—O2Y—C2Y'—C4Y174.8 (15)
C2X'—O2X—C2X—N3X0.4 (14)C5Y'—N3Y'—C2Y'—O2Y174.6 (12)
C2X'—O2X—C2X—C1X177.8 (16)C1Y—N3Y'—C2Y'—O2Y2.8 (11)
C4X—N3X—C2X—O2X0.8 (7)C5Y'—N3Y'—C2Y'—C4Y10.3 (16)
C5X—N3X—C2X—O2X174.6 (4)C1Y—N3Y'—C2Y'—C4Y178.0 (6)
C4X—N3X—C2X—C1X179.1 (4)N3Y—C4Y—C2Y'—O2Y170.7 (15)
C5X—N3X—C2X—C1X7.1 (7)N3Y—C4Y—C2Y'—N3Y'3.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2Y0.84 (4)1.95 (4)2.750 (4)160 (3)
N3A—H3A···O4Bi0.86 (2)1.91 (2)2.770 (3)173 (3)
N6A—H61A···O2Aii0.89 (4)1.97 (4)2.857 (4)176 (4)
N6A—H62A···O2Y0.89 (4)2.17 (4)2.931 (4)143 (3)
N1B—H1B···O2X0.86 (4)1.93 (4)2.746 (4)156 (3)
N3B—H3B···O4A0.89 (2)1.86 (2)2.738 (3)173 (3)
N6B—H61B···O2Bii0.87 (4)2.07 (4)2.902 (4)162 (4)
N6B—H62B···O2X0.85 (4)2.21 (4)2.914 (4)140 (3)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
(Ic) 6-Aminouracil 1-methylpyrrolidin-2-one monosolvate top
Crystal data top
C4H5N3O2·C5H9NOF(000) = 480
Mr = 226.24Dx = 1.429 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5460 reflections
a = 7.5767 (14) Åθ = 3.4–26.0°
b = 21.889 (3) ŵ = 0.11 mm1
c = 7.1356 (11) ÅT = 173 K
β = 117.312 (12)°Needle, colourless
V = 1051.5 (3) Å30.40 × 0.20 × 0.08 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
1984 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source1503 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.118
ω scansθmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 99
Tmin = 0.958, Tmax = 0.992k = 2625
8060 measured reflectionsl = 78
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0947P)2 + 0.2142P]
where P = (Fo2 + 2Fc2)/3
1984 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.28 e Å3
49 restraintsΔρmin = 0.27 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.2004 (3)0.57385 (10)0.6825 (3)0.0296 (5)
H10.233 (4)0.5345 (15)0.711 (5)0.035*
C20.1729 (3)0.61193 (11)0.8184 (4)0.0282 (5)
O20.1797 (3)0.59362 (8)0.9834 (3)0.0356 (5)
N30.1374 (3)0.67143 (9)0.7561 (3)0.0293 (5)
H30.121 (4)0.7007 (13)0.844 (5)0.035*
C40.1308 (3)0.69516 (11)0.5709 (4)0.0296 (6)
O40.1012 (3)0.75085 (8)0.5418 (3)0.0394 (5)
C50.1606 (3)0.65354 (11)0.4387 (4)0.0293 (6)
H50.15690.66700.31030.035*
C60.1954 (3)0.59293 (11)0.4969 (4)0.0288 (5)
N60.2292 (4)0.54936 (11)0.3849 (4)0.0413 (6)
H610.229 (5)0.5592 (16)0.266 (6)0.050*
H620.251 (4)0.5082 (16)0.439 (6)0.050*
O2X0.3104 (3)0.45334 (9)0.7012 (3)0.0442 (5)
C1X0.2884 (10)0.4410 (3)1.0813 (10)0.0380 (14)0.666 (7)
H1X10.28920.42391.20870.057*0.666 (7)
H1X20.15960.46030.99430.057*0.666 (7)
H1X30.39420.47151.12140.057*0.666 (7)
C2X0.3307 (13)0.4029 (3)0.7853 (11)0.0317 (16)0.666 (7)
C3X0.3696 (13)0.3427 (4)0.7118 (13)0.0425 (18)0.666 (7)
H3X10.50210.34280.71630.051*0.666 (7)
H3X20.26810.33450.56510.051*0.666 (7)
C4X0.3606 (7)0.2946 (2)0.8577 (8)0.0477 (14)0.666 (7)
H4X10.48470.27040.92070.057*0.666 (7)
H4X20.24700.26670.78130.057*0.666 (7)
C5X0.3343 (14)0.3304 (3)1.0288 (11)0.0343 (17)0.666 (7)
H5X10.21180.31761.03520.041*0.666 (7)
H5X20.44950.32421.16910.041*0.666 (7)
N1X0.3209 (5)0.39293 (17)0.9633 (7)0.0335 (11)0.666 (7)
C1Y0.401 (3)0.3352 (9)0.664 (3)0.046 (4)0.334 (7)
H1Y10.43200.29150.68420.069*0.334 (7)
H1Y20.51490.35750.66800.069*0.334 (7)
H1Y30.28480.34170.52700.069*0.334 (7)
C2Y0.313 (3)0.4150 (5)0.835 (2)0.036 (4)0.334 (7)
C3Y0.267 (2)0.4223 (6)1.017 (2)0.049 (4)0.334 (7)
H3Y10.35590.45301.11770.059*0.334 (7)
H3Y20.12750.43580.96630.059*0.334 (7)
C4Y0.2979 (14)0.3611 (5)1.1198 (17)0.054 (3)0.334 (7)
H4Y10.18020.34891.13690.065*0.334 (7)
H4Y20.41560.36161.26030.065*0.334 (7)
C5Y0.330 (3)0.3170 (5)0.970 (2)0.039 (4)0.334 (7)
H5Y10.44810.29091.04840.047*0.334 (7)
H5Y20.21230.29060.89360.047*0.334 (7)
N1Y0.3588 (10)0.3572 (4)0.8291 (14)0.039 (2)0.334 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0414 (11)0.0238 (11)0.0272 (11)0.0023 (8)0.0190 (9)0.0027 (9)
C20.0328 (12)0.0275 (12)0.0265 (13)0.0018 (9)0.0156 (10)0.0013 (10)
O20.0535 (11)0.0341 (10)0.0264 (10)0.0005 (8)0.0246 (8)0.0047 (8)
N30.0414 (11)0.0250 (11)0.0279 (11)0.0008 (8)0.0213 (9)0.0003 (9)
C40.0351 (12)0.0296 (13)0.0273 (12)0.0010 (9)0.0171 (10)0.0034 (10)
O40.0654 (12)0.0248 (9)0.0402 (12)0.0051 (8)0.0347 (10)0.0049 (8)
C50.0400 (12)0.0291 (13)0.0239 (13)0.0006 (10)0.0190 (10)0.0023 (10)
C60.0360 (12)0.0302 (13)0.0231 (12)0.0004 (9)0.0160 (10)0.0012 (10)
N60.0727 (17)0.0300 (13)0.0322 (13)0.0080 (11)0.0336 (12)0.0053 (10)
O2X0.0625 (12)0.0298 (11)0.0478 (12)0.0059 (8)0.0318 (10)0.0093 (9)
C1X0.042 (3)0.034 (3)0.042 (3)0.002 (2)0.023 (3)0.001 (3)
C2X0.035 (3)0.026 (4)0.033 (3)0.000 (2)0.014 (2)0.001 (3)
C3X0.045 (3)0.037 (4)0.044 (5)0.001 (3)0.019 (3)0.008 (3)
C4X0.058 (3)0.026 (2)0.045 (3)0.0019 (18)0.012 (2)0.005 (2)
C5X0.043 (3)0.026 (3)0.030 (3)0.007 (3)0.013 (3)0.003 (3)
N1X0.0401 (19)0.026 (2)0.033 (2)0.0017 (14)0.0151 (15)0.0004 (18)
C1Y0.051 (7)0.029 (5)0.053 (8)0.001 (4)0.020 (5)0.012 (5)
C2Y0.030 (5)0.035 (6)0.044 (8)0.001 (4)0.018 (5)0.001 (6)
C3Y0.049 (6)0.046 (8)0.046 (7)0.004 (6)0.016 (5)0.007 (6)
C4Y0.044 (4)0.065 (6)0.053 (6)0.012 (4)0.023 (4)0.014 (5)
C5Y0.043 (5)0.021 (5)0.044 (8)0.001 (4)0.012 (6)0.005 (6)
N1Y0.035 (3)0.038 (5)0.045 (5)0.005 (3)0.019 (3)0.001 (4)
Geometric parameters (Å, º) top
N1—C21.366 (3)C3X—H3X10.9900
N1—C61.373 (3)C3X—H3X20.9900
N1—H10.89 (3)C4X—C5X1.539 (7)
C2—O21.222 (3)C4X—H4X10.9900
C2—N31.363 (3)C4X—H4X20.9900
N3—C41.399 (3)C5X—N1X1.434 (6)
N3—H30.94 (3)C5X—H5X10.9900
C4—O41.240 (3)C5X—H5X20.9900
C4—C51.403 (3)C1Y—N1Y1.438 (11)
C5—C61.379 (3)C1Y—H1Y10.9800
C5—H50.9500C1Y—H1Y20.9800
C6—N61.342 (3)C1Y—H1Y30.9800
N6—H610.87 (4)C2Y—N1Y1.319 (10)
N6—H620.96 (4)C2Y—C3Y1.497 (13)
O2X—C2X1.232 (6)C3Y—C4Y1.493 (13)
O2X—C2Y1.266 (12)C3Y—H3Y10.9900
C1X—N1X1.438 (7)C3Y—H3Y20.9900
C1X—H1X10.9800C4Y—C5Y1.539 (12)
C1X—H1X20.9800C4Y—H4Y10.9900
C1X—H1X30.9800C4Y—H4Y20.9900
C2X—N1X1.324 (7)C5Y—N1Y1.427 (11)
C2X—C3X1.496 (9)C5Y—H5Y10.9900
C3X—C4X1.503 (10)C5Y—H5Y20.9900
C2—N1—C6123.7 (2)H4X1—C4X—H4X2108.8
C2—N1—H1123 (2)N1X—C5X—C4X104.0 (4)
C6—N1—H1113 (2)N1X—C5X—H5X1111.0
O2—C2—N3122.9 (2)C4X—C5X—H5X1111.0
O2—C2—N1122.1 (2)N1X—C5X—H5X2111.0
N3—C2—N1115.0 (2)C4X—C5X—H5X2111.0
C2—N3—C4125.4 (2)H5X1—C5X—H5X2109.0
C2—N3—H3120.0 (18)C2X—N1X—C5X116.3 (5)
C4—N3—H3114.5 (18)C2X—N1X—C1X122.8 (5)
O4—C4—N3116.7 (2)C5X—N1X—C1X120.8 (5)
O4—C4—C5126.8 (2)N1Y—C1Y—H1Y1109.5
N3—C4—C5116.6 (2)N1Y—C1Y—H1Y2109.5
C6—C5—C4119.3 (2)H1Y1—C1Y—H1Y2109.5
C6—C5—H5120.3N1Y—C1Y—H1Y3109.5
C4—C5—H5120.3H1Y1—C1Y—H1Y3109.5
N6—C6—N1115.5 (2)H1Y2—C1Y—H1Y3109.5
N6—C6—C5124.5 (2)O2X—C2Y—N1Y121.5 (10)
N1—C6—C5120.0 (2)O2X—C2Y—C3Y131.0 (9)
C6—N6—H61119 (2)N1Y—C2Y—C3Y107.5 (10)
C6—N6—H62118 (2)C4Y—C3Y—C2Y106.5 (10)
H61—N6—H62123 (3)C4Y—C3Y—H3Y1110.4
N1X—C1X—H1X1109.5C2Y—C3Y—H3Y1110.4
N1X—C1X—H1X2109.5C4Y—C3Y—H3Y2110.4
H1X1—C1X—H1X2109.5C2Y—C3Y—H3Y2110.4
N1X—C1X—H1X3109.5H3Y1—C3Y—H3Y2108.6
H1X1—C1X—H1X3109.5C3Y—C4Y—C5Y105.1 (8)
H1X2—C1X—H1X3109.5C3Y—C4Y—H4Y1110.7
O2X—C2X—N1X124.4 (6)C5Y—C4Y—H4Y1110.7
O2X—C2X—C3X128.3 (6)C3Y—C4Y—H4Y2110.7
N1X—C2X—C3X107.3 (5)C5Y—C4Y—H4Y2110.7
C2X—C3X—C4X107.2 (6)H4Y1—C4Y—H4Y2108.8
C2X—C3X—H3X1110.3N1Y—C5Y—C4Y103.1 (8)
C4X—C3X—H3X1110.3N1Y—C5Y—H5Y1111.1
C2X—C3X—H3X2110.3C4Y—C5Y—H5Y1111.1
C4X—C3X—H3X2110.3N1Y—C5Y—H5Y2111.1
H3X1—C3X—H3X2108.5C4Y—C5Y—H5Y2111.1
C3X—C4X—C5X104.9 (5)H5Y1—C5Y—H5Y2109.1
C3X—C4X—H4X1110.8C2Y—N1Y—C5Y116.0 (9)
C5X—C4X—H4X1110.8C2Y—N1Y—C1Y120.6 (11)
C3X—C4X—H4X2110.8C5Y—N1Y—C1Y122.4 (12)
C5X—C4X—H4X2110.8
C6—N1—C2—O2179.4 (2)O2X—C2X—N1X—C5X175.7 (7)
C6—N1—C2—N30.7 (3)C3X—C2X—N1X—C5X4.2 (9)
O2—C2—N3—C4179.0 (2)O2X—C2X—N1X—C1X1.2 (11)
N1—C2—N3—C41.1 (3)C3X—C2X—N1X—C1X178.9 (5)
C2—N3—C4—O4178.3 (2)C4X—C5X—N1X—C2X0.9 (8)
C2—N3—C4—C51.0 (3)C4X—C5X—N1X—C1X177.9 (5)
O4—C4—C5—C6178.8 (2)C2X—O2X—C2Y—N1Y1.1 (15)
N3—C4—C5—C60.4 (3)C2X—O2X—C2Y—C3Y178 (5)
C2—N1—C6—N6178.8 (2)O2X—C2Y—C3Y—C4Y179.3 (16)
C2—N1—C6—C50.2 (3)N1Y—C2Y—C3Y—C4Y1.6 (17)
C4—C5—C6—N6178.9 (2)C2Y—C3Y—C4Y—C5Y8.9 (16)
C4—C5—C6—N10.1 (3)C3Y—C4Y—C5Y—N1Y12.5 (15)
C2Y—O2X—C2X—N1X5 (2)O2X—C2Y—N1Y—C5Y171.8 (14)
C2Y—O2X—C2X—C3X175 (4)C3Y—C2Y—N1Y—C5Y7.5 (18)
O2X—C2X—C3X—C4X174.2 (7)O2X—C2Y—N1Y—C1Y2 (2)
N1X—C2X—C3X—C4X5.7 (8)C3Y—C2Y—N1Y—C1Y176.9 (13)
C2X—C3X—C4X—C5X5.0 (8)C4Y—C5Y—N1Y—C2Y12.9 (17)
C3X—C4X—C5X—N1X2.7 (7)C4Y—C5Y—N1Y—C1Y178.0 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2X0.89 (3)1.88 (3)2.751 (3)164 (3)
N3—H3···O4i0.94 (3)1.83 (3)2.764 (3)172 (3)
N6—H61···O2ii0.87 (4)2.02 (4)2.881 (3)168 (3)
N6—H62···O2X0.96 (4)2.09 (4)2.936 (3)145 (3)
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y, z1.
 

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