Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961601336X/sk3636sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961601336X/sk3636VIIsup8.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636Isup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636IIsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636IIIsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636IVsup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636Vsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636VIsup14.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961601336X/sk3636VIIsup15.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205322961601336X/sk3636sup16.pdf |
CCDC references: 1499999; 1499998; 1499997; 1499996; 1499995; 1499994; 1499993
Data collection: X-AREA (Stoe & Cie, 2001) for (I), (II), (IV), (V), (VI), (VII); SMART (Siemens, 1995) for (III). Cell refinement: X-AREA (Stoe & Cie, 2001) for (I), (II), (IV), (V), (VI), (VII); SMART (Siemens, 1995) for (III). Data reduction: X-AREA (Stoe & Cie, 2001) for (I), (II), (IV), (V), (VI), (VII); SAINT (Siemens, 1995) for (III). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL (Sheldrick, 2015) for (I), (II), (III), (IV), (V), (VI); SHELXL2014 (Sheldrick, 2015) for (VII). For all compounds, molecular graphics: Mercury (Version 3.8, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C4H6N4 | F(000) = 232 |
Mr = 110.13 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.0330 (17) Å | Cell parameters from 4847 reflections |
b = 4.0256 (3) Å | θ = 3.5–26.2° |
c = 11.5992 (15) Å | µ = 0.10 mm−1 |
β = 118.346 (10)° | T = 173 K |
V = 494.50 (11) Å3 | Block, colourless |
Z = 4 | 0.12 × 0.10 × 0.07 mm |
Stoe IPDS II two-circle diffractometer | 859 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.067 |
ω scans | θmax = 25.8°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −14→14 |
Tmin = 0.599, Tmax = 1.000 | k = −4→4 |
3858 measured reflections | l = −14→14 |
942 independent reflections |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1736P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
942 reflections | Δρmax = 0.18 e Å−3 |
85 parameters | Δρmin = −0.18 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.10545 (11) | 0.5124 (3) | 0.40709 (11) | 0.0234 (3) | |
C2A | 0.19733 (13) | 0.4072 (4) | 0.38121 (13) | 0.0210 (4) | |
N21A | 0.16100 (12) | 0.2171 (4) | 0.27343 (12) | 0.0263 (3) | |
H21A | 0.0819 (15) | 0.154 (5) | 0.2297 (17) | 0.032* | |
H22A | 0.2212 (16) | 0.121 (5) | 0.2652 (18) | 0.032* | |
N3A | 0.32171 (11) | 0.4780 (3) | 0.45018 (11) | 0.0213 (3) | |
C4A | 0.35685 (13) | 0.6656 (4) | 0.55740 (13) | 0.0211 (4) | |
N41A | 0.48219 (12) | 0.7340 (4) | 0.63038 (12) | 0.0269 (4) | |
H41A | 0.5314 (17) | 0.686 (5) | 0.5972 (18) | 0.032* | |
H42A | 0.4998 (17) | 0.895 (4) | 0.6869 (16) | 0.032* | |
C5A | 0.26958 (14) | 0.7780 (4) | 0.59615 (14) | 0.0245 (4) | |
H5A | 0.2949 | 0.9036 | 0.6740 | 0.029* | |
C6A | 0.14574 (14) | 0.6977 (4) | 0.51600 (14) | 0.0244 (4) | |
H6A | 0.0845 | 0.7780 | 0.5388 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0180 (6) | 0.0285 (7) | 0.0227 (6) | 0.0023 (5) | 0.0089 (5) | 0.0040 (5) |
C2A | 0.0185 (7) | 0.0240 (8) | 0.0182 (6) | 0.0005 (5) | 0.0070 (5) | 0.0050 (5) |
N21A | 0.0174 (6) | 0.0372 (8) | 0.0227 (6) | −0.0049 (5) | 0.0081 (5) | −0.0063 (5) |
N3A | 0.0189 (6) | 0.0244 (7) | 0.0196 (6) | 0.0004 (5) | 0.0084 (5) | 0.0011 (5) |
C4A | 0.0201 (7) | 0.0213 (7) | 0.0186 (6) | 0.0017 (5) | 0.0066 (5) | 0.0039 (5) |
N41A | 0.0188 (7) | 0.0346 (8) | 0.0242 (6) | −0.0009 (5) | 0.0078 (5) | −0.0071 (5) |
C5A | 0.0244 (8) | 0.0279 (8) | 0.0216 (7) | 0.0018 (6) | 0.0112 (6) | −0.0006 (6) |
C6A | 0.0233 (8) | 0.0269 (8) | 0.0253 (7) | 0.0053 (6) | 0.0133 (6) | 0.0043 (6) |
N1A—C6A | 1.3439 (19) | C4A—N41A | 1.3619 (19) |
N1A—C2A | 1.3443 (19) | C4A—C5A | 1.399 (2) |
C2A—N21A | 1.3493 (19) | N41A—H41A | 0.867 (15) |
C2A—N3A | 1.3506 (18) | N41A—H42A | 0.874 (15) |
N21A—H21A | 0.876 (15) | C5A—C6A | 1.369 (2) |
N21A—H22A | 0.865 (15) | C5A—H5A | 0.9500 |
N3A—C4A | 1.3403 (19) | C6A—H6A | 0.9500 |
C6A—N1A—C2A | 114.64 (12) | N41A—C4A—C5A | 120.89 (14) |
N1A—C2A—N21A | 116.53 (13) | C4A—N41A—H41A | 117.9 (13) |
N1A—C2A—N3A | 126.78 (13) | C4A—N41A—H42A | 114.8 (12) |
N21A—C2A—N3A | 116.67 (13) | H41A—N41A—H42A | 121.6 (18) |
C2A—N21A—H21A | 119.0 (12) | C6A—C5A—C4A | 116.51 (14) |
C2A—N21A—H22A | 115.8 (12) | C6A—C5A—H5A | 121.7 |
H21A—N21A—H22A | 122.9 (18) | C4A—C5A—H5A | 121.7 |
C4A—N3A—C2A | 116.18 (12) | N1A—C6A—C5A | 124.06 (14) |
N3A—C4A—N41A | 117.33 (13) | N1A—C6A—H6A | 118.0 |
N3A—C4A—C5A | 121.74 (13) | C5A—C6A—H6A | 118.0 |
C6A—N1A—C2A—N21A | 179.29 (13) | C2A—N3A—C4A—C5A | 0.7 (2) |
C6A—N1A—C2A—N3A | −2.3 (2) | N3A—C4A—C5A—C6A | −2.5 (2) |
N1A—C2A—N3A—C4A | 1.9 (2) | N41A—C4A—C5A—C6A | 179.72 (13) |
N21A—C2A—N3A—C4A | −179.69 (12) | C2A—N1A—C6A—C5A | 0.1 (2) |
C2A—N3A—C4A—N41A | 178.51 (12) | C4A—C5A—C6A—N1A | 2.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N1Ai | 0.88 (2) | 2.13 (2) | 2.9947 (18) | 170 (2) |
N41A—H41A···N3Aii | 0.87 (2) | 2.19 (2) | 3.0436 (19) | 169 (2) |
N41A—H42A···N41Aiii | 0.87 (2) | 2.44 (2) | 3.287 (2) | 163 (2) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2. |
C4H6N4·0.5C4H8O2 | F(000) = 328 |
Mr = 154.18 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6282 (14) Å | Cell parameters from 5777 reflections |
b = 7.2157 (9) Å | θ = 3.6–26.0° |
c = 13.879 (2) Å | µ = 0.10 mm−1 |
β = 102.243 (15)° | T = 173 K |
V = 746.6 (2) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.27 mm |
Stoe IPDS II two-circle diffractometer | 1261 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.031 |
ω scans | θmax = 25.6°, θmin = 3.9° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→8 |
Tmin = 0.659, Tmax = 1.000 | k = −8→8 |
4207 measured reflections | l = −16→16 |
1388 independent reflections |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0412P)2 + 0.3097P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
1388 reflections | Δρmax = 0.20 e Å−3 |
112 parameters | Δρmin = −0.18 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.75873 (16) | 0.66790 (15) | 0.70609 (9) | 0.0235 (3) | |
C2A | 0.85588 (18) | 0.51618 (17) | 0.69617 (9) | 0.0188 (3) | |
N21A | 1.03684 (16) | 0.52854 (16) | 0.72415 (9) | 0.0243 (3) | |
H21A | 1.074 (2) | 0.626 (2) | 0.7623 (12) | 0.029* | |
H22A | 1.095 (2) | 0.420 (2) | 0.7363 (12) | 0.029* | |
N3A | 0.79084 (15) | 0.35175 (15) | 0.65921 (8) | 0.0194 (3) | |
C4A | 0.61275 (18) | 0.33566 (18) | 0.62983 (9) | 0.0198 (3) | |
N41A | 0.55124 (16) | 0.16881 (17) | 0.59471 (10) | 0.0272 (3) | |
H42A | 0.4348 (19) | 0.149 (2) | 0.5746 (13) | 0.033* | |
H41A | 0.631 (2) | 0.087 (2) | 0.5877 (13) | 0.033* | |
C5A | 0.49884 (19) | 0.4861 (2) | 0.63736 (10) | 0.0248 (3) | |
H5A | 0.3722 | 0.4767 | 0.6170 | 0.030* | |
C6A | 0.58051 (19) | 0.6459 (2) | 0.67547 (11) | 0.0254 (3) | |
H6A | 0.5061 | 0.7493 | 0.6808 | 0.031* | |
O1X | 0.81612 (13) | −0.03406 (14) | 0.49648 (7) | 0.0265 (3) | |
C1X | 0.94006 (19) | −0.1825 (2) | 0.49452 (11) | 0.0260 (3) | |
H1X1 | 0.9411 | −0.2145 | 0.4253 | 0.031* | |
H1X2 | 0.9011 | −0.2934 | 0.5264 | 0.031* | |
C2X | 0.87426 (19) | 0.1282 (2) | 0.45266 (11) | 0.0269 (3) | |
H2X1 | 0.7902 | 0.2315 | 0.4558 | 0.032* | |
H2X2 | 0.8736 | 0.1036 | 0.3824 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0236 (6) | 0.0170 (6) | 0.0293 (6) | 0.0019 (4) | 0.0039 (5) | −0.0007 (5) |
C2A | 0.0217 (7) | 0.0163 (6) | 0.0182 (6) | −0.0006 (5) | 0.0038 (5) | 0.0023 (5) |
N21A | 0.0192 (6) | 0.0157 (6) | 0.0357 (7) | −0.0011 (5) | 0.0010 (5) | −0.0029 (5) |
N3A | 0.0183 (6) | 0.0168 (6) | 0.0225 (6) | −0.0002 (4) | 0.0029 (4) | −0.0010 (4) |
C4A | 0.0198 (7) | 0.0207 (7) | 0.0186 (6) | −0.0006 (5) | 0.0033 (5) | 0.0009 (5) |
N41A | 0.0167 (6) | 0.0235 (6) | 0.0399 (7) | −0.0020 (5) | 0.0028 (5) | −0.0084 (5) |
C5A | 0.0176 (7) | 0.0255 (7) | 0.0301 (7) | 0.0028 (5) | 0.0027 (5) | −0.0010 (6) |
C6A | 0.0243 (7) | 0.0220 (7) | 0.0295 (7) | 0.0068 (6) | 0.0045 (6) | 0.0003 (6) |
O1X | 0.0170 (5) | 0.0286 (6) | 0.0344 (6) | 0.0007 (4) | 0.0068 (4) | −0.0020 (4) |
C1X | 0.0240 (7) | 0.0237 (7) | 0.0312 (7) | 0.0009 (6) | 0.0080 (6) | −0.0020 (6) |
C2X | 0.0245 (7) | 0.0282 (7) | 0.0273 (7) | 0.0056 (6) | 0.0040 (6) | 0.0023 (6) |
N1A—C6A | 1.3450 (19) | C5A—C6A | 1.363 (2) |
N1A—C2A | 1.3452 (17) | C5A—H5A | 0.9500 |
C2A—N3A | 1.3450 (17) | C6A—H6A | 0.9500 |
C2A—N21A | 1.3553 (18) | O1X—C1X | 1.4327 (17) |
N21A—H21A | 0.891 (14) | O1X—C2X | 1.4324 (18) |
N21A—H22A | 0.895 (14) | C1X—C2Xi | 1.502 (2) |
N3A—C4A | 1.3380 (17) | C1X—H1X1 | 0.9900 |
C4A—N41A | 1.3454 (18) | C1X—H1X2 | 0.9900 |
C4A—C5A | 1.4079 (19) | C2X—C1Xi | 1.502 (2) |
N41A—H42A | 0.884 (14) | C2X—H2X1 | 0.9900 |
N41A—H41A | 0.870 (14) | C2X—H2X2 | 0.9900 |
C6A—N1A—C2A | 114.42 (11) | N1A—C6A—C5A | 124.80 (12) |
N1A—C2A—N3A | 126.17 (12) | N1A—C6A—H6A | 117.6 |
N1A—C2A—N21A | 117.83 (12) | C5A—C6A—H6A | 117.6 |
N3A—C2A—N21A | 115.99 (11) | C1X—O1X—C2X | 109.76 (10) |
C2A—N21A—H21A | 113.6 (11) | O1X—C1X—C2Xi | 110.70 (12) |
C2A—N21A—H22A | 115.3 (11) | O1X—C1X—H1X1 | 109.5 |
H21A—N21A—H22A | 119.7 (15) | C2Xi—C1X—H1X1 | 109.5 |
C4A—N3A—C2A | 117.47 (11) | O1X—C1X—H1X2 | 109.5 |
N3A—C4A—N41A | 116.21 (12) | C2Xi—C1X—H1X2 | 109.5 |
N3A—C4A—C5A | 120.88 (12) | H1X1—C1X—H1X2 | 108.1 |
N41A—C4A—C5A | 122.91 (13) | O1X—C2X—C1Xi | 110.53 (11) |
C4A—N41A—H42A | 120.6 (11) | O1X—C2X—H2X1 | 109.5 |
C4A—N41A—H41A | 116.7 (12) | C1Xi—C2X—H2X1 | 109.5 |
H42A—N41A—H41A | 122.5 (16) | O1X—C2X—H2X2 | 109.5 |
C6A—C5A—C4A | 116.26 (13) | C1Xi—C2X—H2X2 | 109.5 |
C6A—C5A—H5A | 121.9 | H2X1—C2X—H2X2 | 108.1 |
C4A—C5A—H5A | 121.9 | ||
C6A—N1A—C2A—N3A | 0.3 (2) | N3A—C4A—C5A—C6A | 0.2 (2) |
C6A—N1A—C2A—N21A | 179.06 (12) | N41A—C4A—C5A—C6A | 179.24 (13) |
N1A—C2A—N3A—C4A | −0.43 (19) | C2A—N1A—C6A—C5A | 0.2 (2) |
N21A—C2A—N3A—C4A | −179.24 (11) | C4A—C5A—C6A—N1A | −0.4 (2) |
C2A—N3A—C4A—N41A | −178.93 (12) | C2X—O1X—C1X—C2Xi | 57.71 (16) |
C2A—N3A—C4A—C5A | 0.17 (18) | C1X—O1X—C2X—C1Xi | −57.62 (16) |
Symmetry code: (i) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N3Aii | 0.89 (1) | 2.10 (1) | 2.9809 (16) | 168 (2) |
N21A—H22A···N1Aiii | 0.90 (1) | 2.20 (1) | 3.0824 (17) | 170 (2) |
N41A—H42A···O1Xiv | 0.88 (1) | 2.13 (2) | 2.9826 (17) | 163 (2) |
N41A—H41A···O1X | 0.87 (1) | 2.26 (2) | 3.0418 (17) | 150 (2) |
Symmetry codes: (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, −y, −z+1. |
C4H6N4·C4H9NO | Z = 2 |
Mr = 197.25 | F(000) = 212 |
Triclinic, P1 | Dx = 1.263 Mg m−3 |
a = 8.0055 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.0256 (10) Å | Cell parameters from 2889 reflections |
c = 9.3143 (11) Å | θ = 3–23° |
α = 81.779 (2)° | µ = 0.09 mm−1 |
β = 78.053 (2)° | T = 180 K |
γ = 62.518 (2)° | Block, colourless |
V = 518.63 (11) Å3 | 0.50 × 0.40 × 0.40 mm |
Siemens CCD three-circle diffractometer | 1346 reflections with I > 2σ(I) |
ω scans | Rint = 0.111 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.2°, θmin = 2.2° |
Tmin = 0.648, Tmax = 1.000 | h = −10→10 |
5287 measured reflections | k = −10→10 |
2204 independent reflections | l = −11→12 |
Refinement on F2 | 132 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.286 | w = 1/[σ2(Fo2) + (0.1438P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.004 |
2204 reflections | Δρmax = 0.40 e Å−3 |
161 parameters | Δρmin = −0.44 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The used target distances were 1.52 (1) Å for d(C1X/Y,C2X/Y) and d(C31X/Y,C2X'/Y'), 1.25 (1) Å for d(C2X/Y,O21X/Y) and d(C2X'/Y',O21X/Y), 1.30 (1) Å for d(C2X/Y,N3X/Y) and d(C2X'/Y',N3X'/Y'), 1.47 (1) Å for d(N3X/Y,C31X/Y), d(N3X/Y,C32X/Y), d(N3X'/Y',C1X/Y) and d(N3X'/Y',C32X/Y), 2.42 (2) Å for d(O21X/Y,C1X/Y) and d(O21X/Y,C31X/Y), 2.23 (2) Å for d(O21X/Y,N3X/Y) and d(O21X/Y,N3X'/Y'), 2.41 (2) Å for d(C1X/Y,N3X/Y) and d(C31X/Y,N3X'/Y'), 2.41 (2) Å for d(C2X/Y,C31X/Y) and d(C2X'/Y',C1X/Y), 2.43 (2) Å for d(C2X/Y,C32X/Y) and d(C2X'/Y',C32X/Y), and 2.52 (2) Å for d(C31X/Y,C32X/Y) and d(C1X/Y,C32X/Y). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.4732 (4) | 0.8072 (4) | 0.1346 (3) | 0.0350 (8) | |
C2A | 0.3274 (4) | 0.9497 (4) | 0.2107 (4) | 0.0278 (8) | |
N21A | 0.2895 (4) | 1.1261 (4) | 0.1531 (4) | 0.0393 (9) | |
H21A | 0.191 (4) | 1.214 (4) | 0.209 (4) | 0.047* | |
H22A | 0.357 (5) | 1.143 (5) | 0.067 (3) | 0.047* | |
N3A | 0.2167 (4) | 0.9340 (4) | 0.3361 (3) | 0.0292 (7) | |
C4A | 0.2544 (5) | 0.7604 (4) | 0.3956 (3) | 0.0272 (8) | |
N41A | 0.1479 (4) | 0.7454 (4) | 0.5218 (3) | 0.0370 (8) | |
H41A | 0.047 (4) | 0.838 (4) | 0.566 (4) | 0.044* | |
H42A | 0.154 (5) | 0.638 (4) | 0.562 (4) | 0.044* | |
C5A | 0.4054 (5) | 0.6019 (5) | 0.3255 (4) | 0.0350 (9) | |
H5A | 0.4354 | 0.4774 | 0.3651 | 0.042* | |
C6A | 0.5045 (5) | 0.6371 (5) | 0.1993 (4) | 0.0369 (9) | |
H6A | 0.6064 | 0.5313 | 0.1516 | 0.044* | |
C1X | −0.0800 (6) | 0.3330 (6) | 0.9231 (4) | 0.0534 (11) | |
H1XA | 0.0035 | 0.2812 | 0.9980 | 0.080* | 0.808 (7) |
H1XB | −0.1340 | 0.2478 | 0.9152 | 0.080* | 0.808 (7) |
H1XC | −0.1835 | 0.4563 | 0.9510 | 0.080* | 0.808 (7) |
H1XD | −0.1027 | 0.2494 | 1.0038 | 0.080* | 0.192 (7) |
H1XE | −0.0437 | 0.4176 | 0.9607 | 0.080* | 0.192 (7) |
H1XF | −0.1967 | 0.4073 | 0.8801 | 0.080* | 0.192 (7) |
O21X | 0.0132 (4) | 0.5078 (3) | 0.7128 (3) | 0.0445 (8) | |
C31X | 0.2694 (5) | 0.2146 (5) | 0.5704 (4) | 0.0456 (10) | |
H3XA | 0.1908 | 0.3304 | 0.5174 | 0.068* | 0.808 (7) |
H3XB | 0.3042 | 0.1061 | 0.5138 | 0.068* | 0.808 (7) |
H3XC | 0.3855 | 0.2194 | 0.5836 | 0.068* | 0.808 (7) |
H3XD | 0.3122 | 0.0799 | 0.5954 | 0.068* | 0.192 (7) |
H3XE | 0.2178 | 0.2478 | 0.4781 | 0.068* | 0.192 (7) |
H3XF | 0.3776 | 0.2440 | 0.5589 | 0.068* | 0.192 (7) |
C32X | 0.2036 (7) | 0.0120 (5) | 0.7926 (6) | 0.0637 (14) | |
H4XA | 0.2050 | 0.0210 | 0.8961 | 0.096* | 0.808 (7) |
H4XB | 0.3283 | −0.0826 | 0.7486 | 0.096* | 0.808 (7) |
H4XC | 0.1047 | −0.0248 | 0.7856 | 0.096* | 0.808 (7) |
H4XD | 0.1693 | −0.0585 | 0.8786 | 0.096* | 0.192 (7) |
H4XE | 0.1871 | −0.0270 | 0.7036 | 0.096* | 0.192 (7) |
H4XF | 0.3370 | −0.0134 | 0.7856 | 0.096* | 0.192 (7) |
C2X | 0.0343 (6) | 0.3544 (6) | 0.7763 (5) | 0.0353 (12) | 0.808 (7) |
N3X | 0.1626 (5) | 0.1969 (5) | 0.7131 (4) | 0.0383 (12) | 0.808 (7) |
C2X' | 0.1122 (19) | 0.3290 (11) | 0.6951 (13) | 0.032 (4) | 0.192 (7) |
N3X' | 0.0777 (16) | 0.2178 (11) | 0.8076 (12) | 0.034 (4) | 0.192 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0329 (16) | 0.0252 (16) | 0.0372 (17) | −0.0077 (13) | 0.0045 (13) | −0.0061 (13) |
C2A | 0.0222 (17) | 0.0211 (17) | 0.036 (2) | −0.0053 (13) | −0.0044 (14) | −0.0047 (13) |
N21A | 0.0396 (19) | 0.0199 (15) | 0.0411 (19) | −0.0045 (13) | 0.0084 (14) | −0.0028 (13) |
N3A | 0.0273 (15) | 0.0220 (14) | 0.0326 (16) | −0.0060 (12) | −0.0045 (12) | −0.0030 (11) |
C4A | 0.0289 (18) | 0.0212 (17) | 0.0308 (19) | −0.0093 (14) | −0.0074 (15) | −0.0030 (13) |
N41A | 0.0366 (17) | 0.0179 (15) | 0.0440 (19) | −0.0055 (13) | 0.0045 (14) | −0.0036 (13) |
C5A | 0.0317 (19) | 0.0180 (17) | 0.046 (2) | −0.0043 (14) | −0.0016 (16) | −0.0035 (14) |
C6A | 0.035 (2) | 0.0202 (18) | 0.040 (2) | −0.0024 (15) | 0.0031 (16) | −0.0073 (14) |
C1X | 0.052 (3) | 0.059 (3) | 0.046 (2) | −0.023 (2) | −0.0052 (19) | −0.001 (2) |
O21X | 0.0479 (16) | 0.0211 (13) | 0.0535 (17) | −0.0097 (11) | 0.0000 (13) | −0.0011 (11) |
C31X | 0.036 (2) | 0.037 (2) | 0.058 (2) | −0.0086 (17) | −0.0013 (18) | −0.0209 (18) |
C32X | 0.070 (3) | 0.0178 (19) | 0.104 (4) | −0.0106 (19) | −0.043 (3) | 0.004 (2) |
C2X | 0.036 (3) | 0.030 (3) | 0.040 (3) | −0.014 (2) | −0.011 (2) | 0.003 (2) |
N3X | 0.032 (2) | 0.025 (2) | 0.053 (3) | −0.0074 (18) | −0.0078 (18) | −0.0065 (18) |
C2X' | 0.035 (9) | 0.032 (6) | 0.044 (9) | −0.030 (7) | 0.001 (6) | −0.008 (6) |
N3X' | 0.030 (8) | 0.024 (6) | 0.048 (8) | −0.010 (6) | −0.016 (5) | 0.008 (6) |
N1A—C6A | 1.342 (4) | C1X—H1XF | 0.9800 |
N1A—C2A | 1.353 (4) | O21X—C2X | 1.240 (4) |
C2A—N3A | 1.341 (4) | O21X—C2X' | 1.296 (8) |
C2A—N21A | 1.355 (4) | C31X—N3X | 1.451 (5) |
N21A—H21A | 0.898 (19) | C31X—C2X' | 1.552 (8) |
N21A—H22A | 0.901 (19) | C31X—H3XA | 0.9800 |
N3A—C4A | 1.342 (4) | C31X—H3XB | 0.9800 |
C4A—N41A | 1.328 (5) | C31X—H3XC | 0.9800 |
C4A—C5A | 1.413 (5) | C31X—H3XD | 0.9800 |
N41A—H41A | 0.875 (19) | C31X—H3XE | 0.9800 |
N41A—H42A | 0.876 (19) | C31X—H3XF | 0.9800 |
C5A—C6A | 1.348 (5) | C32X—N3X | 1.482 (5) |
C5A—H5A | 0.9500 | C32X—N3X' | 1.495 (7) |
C6A—H6A | 0.9500 | C32X—H4XA | 0.9800 |
C1X—N3X' | 1.500 (8) | C32X—H4XB | 0.9800 |
C1X—C2X | 1.515 (5) | C32X—H4XC | 0.9800 |
C1X—H1XA | 0.9800 | C32X—H4XD | 0.9800 |
C1X—H1XB | 0.9800 | C32X—H4XE | 0.9800 |
C1X—H1XC | 0.9800 | C32X—H4XF | 0.9800 |
C1X—H1XD | 0.9800 | C2X—N3X | 1.328 (5) |
C1X—H1XE | 0.9800 | C2X'—N3X' | 1.346 (9) |
C6A—N1A—C2A | 113.0 (3) | H3XA—C31X—H3XB | 109.5 |
N3A—C2A—N1A | 126.7 (3) | N3X—C31X—H3XC | 109.5 |
N3A—C2A—N21A | 117.0 (3) | H3XA—C31X—H3XC | 109.5 |
N1A—C2A—N21A | 116.3 (3) | H3XB—C31X—H3XC | 109.5 |
C2A—N21A—H21A | 112 (2) | C2X'—C31X—H3XD | 109.5 |
C2A—N21A—H22A | 120 (2) | C2X'—C31X—H3XE | 109.5 |
H21A—N21A—H22A | 128 (3) | H3XD—C31X—H3XE | 109.5 |
C2A—N3A—C4A | 117.7 (3) | C2X'—C31X—H3XF | 109.5 |
N41A—C4A—N3A | 117.6 (3) | H3XD—C31X—H3XF | 109.5 |
N41A—C4A—C5A | 122.4 (3) | H3XE—C31X—H3XF | 109.5 |
N3A—C4A—C5A | 120.0 (3) | N3X—C32X—H4XA | 109.5 |
C4A—N41A—H41A | 126 (3) | N3X—C32X—H4XB | 109.5 |
C4A—N41A—H42A | 123 (3) | H4XA—C32X—H4XB | 109.5 |
H41A—N41A—H42A | 110 (4) | N3X—C32X—H4XC | 109.5 |
C6A—C5A—C4A | 116.3 (3) | H4XA—C32X—H4XC | 109.5 |
C6A—C5A—H5A | 121.8 | H4XB—C32X—H4XC | 109.5 |
C4A—C5A—H5A | 121.8 | N3X'—C32X—H4XD | 109.5 |
N1A—C6A—C5A | 126.3 (3) | N3X'—C32X—H4XE | 109.5 |
N1A—C6A—H6A | 116.9 | H4XD—C32X—H4XE | 109.5 |
C5A—C6A—H6A | 116.9 | N3X'—C32X—H4XF | 109.5 |
C2X—C1X—H1XA | 109.5 | H4XD—C32X—H4XF | 109.5 |
C2X—C1X—H1XB | 109.5 | H4XE—C32X—H4XF | 109.5 |
H1XA—C1X—H1XB | 109.5 | O21X—C2X—N3X | 119.1 (4) |
C2X—C1X—H1XC | 109.5 | O21X—C2X—C1X | 124.1 (4) |
H1XA—C1X—H1XC | 109.5 | N3X—C2X—C1X | 116.8 (4) |
H1XB—C1X—H1XC | 109.5 | C2X—N3X—C31X | 117.6 (3) |
N3X'—C1X—H1XD | 109.5 | C2X—N3X—C32X | 120.2 (4) |
N3X'—C1X—H1XE | 109.5 | C31X—N3X—C32X | 122.0 (3) |
H1XD—C1X—H1XE | 109.5 | O21X—C2X'—N3X' | 114.9 (7) |
N3X'—C1X—H1XF | 109.5 | O21X—C2X'—C31X | 132.7 (7) |
H1XD—C1X—H1XF | 109.5 | N3X'—C2X'—C31X | 112.4 (6) |
H1XE—C1X—H1XF | 109.5 | C2X'—N3X'—C32X | 114.7 (6) |
N3X—C31X—H3XA | 109.5 | C2X'—N3X'—C1X | 110.8 (6) |
N3X—C31X—H3XB | 109.5 | C32X—N3X'—C1X | 134.5 (7) |
C6A—N1A—C2A—N3A | −1.5 (5) | C4A—C5A—C6A—N1A | −0.1 (6) |
C6A—N1A—C2A—N21A | 178.9 (3) | O21X—C2X—N3X—C31X | −1.0 (6) |
N1A—C2A—N3A—C4A | 1.4 (5) | C1X—C2X—N3X—C31X | 178.2 (4) |
N21A—C2A—N3A—C4A | −179.0 (3) | O21X—C2X—N3X—C32X | 174.2 (4) |
C2A—N3A—C4A—N41A | 178.2 (3) | C1X—C2X—N3X—C32X | −6.5 (6) |
C2A—N3A—C4A—C5A | −0.5 (5) | O21X—C2X'—N3X'—C32X | −175.0 (11) |
N41A—C4A—C5A—C6A | −178.8 (3) | C31X—C2X'—N3X'—C32X | 3.2 (18) |
N3A—C4A—C5A—C6A | −0.1 (5) | O21X—C2X'—N3X'—C1X | 3.9 (19) |
C2A—N1A—C6A—C5A | 0.8 (5) | C31X—C2X'—N3X'—C1X | −177.8 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···O21Xi | 0.90 (2) | 2.19 (2) | 3.048 (4) | 159 (3) |
N21A—H22A···N1Aii | 0.90 (2) | 2.18 (2) | 3.082 (4) | 177 (3) |
N41A—H41A···N3Ai | 0.88 (2) | 2.18 (2) | 3.055 (4) | 175 (3) |
N41A—H42A···O21X | 0.88 (2) | 2.08 (3) | 2.845 (4) | 145 (3) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z. |
C4H6N4·C5H9NO | F(000) = 896 |
Mr = 209.26 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3870 (6) Å | Cell parameters from 16446 reflections |
b = 24.8978 (13) Å | θ = 2.4–26.4° |
c = 11.5485 (8) Å | µ = 0.09 mm−1 |
β = 98.824 (6)° | T = 173 K |
V = 2098.9 (3) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.16 × 0.15 mm |
Stoe IPDS II two-circle diffractometer | 3339 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.111 |
ω scans | θmax = 25.9°, θmin = 2.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −8→9 |
Tmin = 0.194, Tmax = 1.000 | k = −30→27 |
17082 measured reflections | l = −14→14 |
4062 independent reflections |
Refinement on F2 | 8 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0994P)2 + 0.1405P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4062 reflections | Δρmax = 0.36 e Å−3 |
297 parameters | Δρmin = −0.25 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.8466 (2) | 0.92283 (6) | 0.91180 (12) | 0.0395 (3) | |
C2A | 0.7608 (2) | 0.88052 (7) | 0.85425 (13) | 0.0363 (4) | |
N21A | 0.7397 (2) | 0.83619 (7) | 0.91627 (12) | 0.0451 (4) | |
H21A | 0.804 (3) | 0.8302 (9) | 0.9867 (16) | 0.054* | |
H22A | 0.677 (3) | 0.8094 (8) | 0.8838 (19) | 0.054* | |
N3A | 0.69106 (19) | 0.87863 (6) | 0.73885 (11) | 0.0365 (3) | |
C4A | 0.7118 (2) | 0.92281 (7) | 0.67513 (14) | 0.0361 (4) | |
N41A | 0.6440 (2) | 0.92058 (7) | 0.56008 (12) | 0.0440 (4) | |
H41A | 0.591 (3) | 0.8903 (8) | 0.5304 (19) | 0.053* | |
H42A | 0.666 (3) | 0.9478 (8) | 0.5167 (18) | 0.053* | |
C5A | 0.8009 (2) | 0.96867 (7) | 0.72661 (15) | 0.0413 (4) | |
H5A | 0.8168 | 0.9999 | 0.6820 | 0.050* | |
C6A | 0.8640 (2) | 0.96610 (7) | 0.84460 (15) | 0.0410 (4) | |
H6A | 0.9238 | 0.9968 | 0.8812 | 0.049* | |
N1B | 0.5151 (2) | 0.74305 (6) | 0.82160 (12) | 0.0433 (4) | |
C2B | 0.4893 (2) | 0.73115 (7) | 0.70680 (13) | 0.0362 (4) | |
N21B | 0.5265 (2) | 0.77089 (7) | 0.63497 (13) | 0.0451 (4) | |
H21B | 0.563 (3) | 0.8036 (7) | 0.6624 (19) | 0.054* | |
H22B | 0.502 (3) | 0.7658 (9) | 0.5588 (14) | 0.054* | |
N3B | 0.43290 (19) | 0.68381 (6) | 0.65801 (11) | 0.0372 (3) | |
C4B | 0.3932 (2) | 0.64481 (7) | 0.73086 (14) | 0.0378 (4) | |
N41B | 0.3431 (2) | 0.59697 (7) | 0.68401 (14) | 0.0480 (4) | |
H41B | 0.346 (3) | 0.5905 (10) | 0.6102 (15) | 0.058* | |
H42B | 0.307 (3) | 0.5704 (8) | 0.7274 (19) | 0.058* | |
C5B | 0.4067 (3) | 0.65426 (8) | 0.85183 (14) | 0.0439 (4) | |
H5B | 0.3733 | 0.6277 | 0.9037 | 0.053* | |
C6B | 0.4698 (3) | 0.70317 (8) | 0.89083 (14) | 0.0468 (4) | |
H6B | 0.4830 | 0.7098 | 0.9727 | 0.056* | |
N1X | 0.4463 (2) | 0.80203 (7) | 0.23003 (13) | 0.0475 (4) | |
C11X | 0.5109 (3) | 0.74788 (9) | 0.2514 (2) | 0.0595 (5) | |
H11A | 0.5484 | 0.7425 | 0.3357 | 0.089* | |
H11B | 0.6158 | 0.7416 | 0.2105 | 0.089* | |
H11C | 0.4125 | 0.7226 | 0.2224 | 0.089* | |
C2X | 0.4312 (3) | 0.83708 (8) | 0.31469 (14) | 0.0439 (4) | |
O21X | 0.4678 (2) | 0.82850 (6) | 0.42080 (10) | 0.0521 (4) | |
C3X | 0.3605 (3) | 0.88984 (8) | 0.25974 (16) | 0.0488 (4) | |
H3X1 | 0.4462 | 0.9195 | 0.2863 | 0.059* | |
H3X2 | 0.2389 | 0.8985 | 0.2808 | 0.059* | |
C4X | 0.3473 (3) | 0.88132 (10) | 0.12855 (18) | 0.0593 (6) | |
H4X1 | 0.4360 | 0.9046 | 0.0961 | 0.071* | |
H4X2 | 0.2225 | 0.8898 | 0.0883 | 0.071* | |
C5X | 0.3916 (3) | 0.82237 (9) | 0.11235 (15) | 0.0532 (5) | |
H5X1 | 0.2827 | 0.8029 | 0.0725 | 0.064* | |
H5X2 | 0.4923 | 0.8185 | 0.0654 | 0.064* | |
N1Y | 0.20909 (19) | 0.44410 (6) | 0.73683 (11) | 0.0384 (3) | |
C11Y | 0.1258 (3) | 0.46997 (8) | 0.62969 (14) | 0.0455 (4) | |
H11D | 0.0799 | 0.5054 | 0.6479 | 0.068* | |
H11E | 0.0238 | 0.4480 | 0.5914 | 0.068* | |
H11F | 0.2171 | 0.4741 | 0.5771 | 0.068* | |
C2Y | 0.2502 (2) | 0.46988 (7) | 0.83867 (13) | 0.0374 (4) | |
O21Y | 0.22478 (19) | 0.51838 (5) | 0.85396 (10) | 0.0448 (3) | |
C3Y | 0.3332 (3) | 0.43090 (8) | 0.93077 (15) | 0.0442 (4) | |
H3Y1 | 0.2573 | 0.4282 | 0.9941 | 0.053* | |
H3Y2 | 0.4581 | 0.4424 | 0.9653 | 0.053* | |
C4Y | 0.3393 (3) | 0.37713 (8) | 0.86795 (16) | 0.0476 (4) | |
H4Y1 | 0.2642 | 0.3501 | 0.9016 | 0.057* | |
H4Y2 | 0.4668 | 0.3638 | 0.8753 | 0.057* | |
C5Y | 0.2616 (3) | 0.38793 (8) | 0.73922 (16) | 0.0444 (4) | |
H5Y1 | 0.3554 | 0.3814 | 0.6881 | 0.053* | |
H5Y2 | 0.1542 | 0.3648 | 0.7131 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0413 (7) | 0.0428 (8) | 0.0349 (7) | −0.0015 (6) | 0.0077 (5) | −0.0021 (5) |
C2A | 0.0360 (8) | 0.0428 (10) | 0.0314 (7) | 0.0018 (6) | 0.0098 (6) | −0.0002 (6) |
N21A | 0.0599 (10) | 0.0451 (9) | 0.0290 (7) | −0.0084 (7) | 0.0030 (6) | 0.0027 (6) |
N3A | 0.0408 (8) | 0.0412 (8) | 0.0291 (6) | −0.0008 (6) | 0.0102 (5) | 0.0005 (5) |
C4A | 0.0373 (8) | 0.0387 (9) | 0.0345 (8) | 0.0034 (6) | 0.0131 (6) | 0.0025 (6) |
N41A | 0.0576 (9) | 0.0444 (9) | 0.0309 (7) | −0.0049 (7) | 0.0093 (6) | 0.0037 (6) |
C5A | 0.0450 (9) | 0.0422 (10) | 0.0394 (8) | 0.0010 (7) | 0.0148 (7) | 0.0030 (7) |
C6A | 0.0410 (9) | 0.0421 (10) | 0.0410 (8) | −0.0020 (7) | 0.0101 (7) | −0.0041 (7) |
N1B | 0.0542 (9) | 0.0443 (9) | 0.0309 (7) | −0.0021 (7) | 0.0050 (6) | 0.0018 (6) |
C2B | 0.0379 (8) | 0.0392 (9) | 0.0313 (7) | 0.0014 (6) | 0.0052 (6) | 0.0024 (6) |
N21B | 0.0639 (10) | 0.0396 (9) | 0.0316 (7) | −0.0057 (7) | 0.0067 (6) | 0.0032 (6) |
N3B | 0.0413 (7) | 0.0387 (8) | 0.0316 (6) | −0.0013 (6) | 0.0053 (5) | 0.0028 (5) |
C4B | 0.0364 (8) | 0.0412 (9) | 0.0354 (8) | 0.0001 (7) | 0.0040 (6) | 0.0041 (6) |
N41B | 0.0623 (10) | 0.0435 (9) | 0.0381 (8) | −0.0102 (7) | 0.0075 (7) | 0.0033 (6) |
C5B | 0.0522 (10) | 0.0460 (10) | 0.0340 (8) | −0.0026 (8) | 0.0082 (7) | 0.0076 (7) |
C6B | 0.0613 (11) | 0.0504 (11) | 0.0289 (7) | −0.0005 (8) | 0.0073 (7) | 0.0024 (7) |
N1X | 0.0535 (9) | 0.0533 (10) | 0.0371 (7) | −0.0038 (7) | 0.0119 (6) | −0.0024 (6) |
C11X | 0.0578 (12) | 0.0524 (13) | 0.0690 (13) | 0.0005 (9) | 0.0118 (10) | −0.0054 (9) |
C2X | 0.0463 (10) | 0.0525 (11) | 0.0343 (8) | −0.0094 (8) | 0.0108 (7) | −0.0007 (7) |
O21X | 0.0698 (9) | 0.0574 (9) | 0.0291 (6) | −0.0062 (6) | 0.0078 (5) | 0.0032 (5) |
C3X | 0.0506 (10) | 0.0498 (11) | 0.0468 (10) | −0.0055 (8) | 0.0096 (8) | 0.0019 (8) |
C4X | 0.0627 (13) | 0.0701 (15) | 0.0444 (10) | −0.0088 (10) | 0.0060 (9) | 0.0138 (9) |
C5X | 0.0593 (12) | 0.0712 (14) | 0.0317 (8) | −0.0145 (10) | 0.0154 (7) | −0.0020 (8) |
N1Y | 0.0411 (8) | 0.0408 (8) | 0.0343 (7) | −0.0004 (6) | 0.0092 (5) | −0.0017 (5) |
C11Y | 0.0490 (10) | 0.0547 (11) | 0.0328 (8) | −0.0027 (8) | 0.0067 (7) | −0.0012 (7) |
C2Y | 0.0393 (8) | 0.0419 (10) | 0.0335 (7) | −0.0021 (7) | 0.0131 (6) | −0.0007 (6) |
O21Y | 0.0606 (8) | 0.0401 (7) | 0.0355 (6) | 0.0014 (5) | 0.0127 (5) | −0.0020 (5) |
C3Y | 0.0474 (10) | 0.0482 (11) | 0.0384 (8) | 0.0020 (8) | 0.0110 (7) | 0.0048 (7) |
C4Y | 0.0496 (10) | 0.0429 (11) | 0.0517 (10) | 0.0004 (8) | 0.0123 (8) | 0.0050 (7) |
C5Y | 0.0448 (9) | 0.0415 (10) | 0.0491 (10) | −0.0025 (7) | 0.0141 (7) | −0.0068 (7) |
N1A—C6A | 1.345 (2) | N1X—C5X | 1.448 (2) |
N1A—C2A | 1.350 (2) | C11X—H11A | 0.9800 |
C2A—N21A | 1.338 (2) | C11X—H11B | 0.9800 |
C2A—N3A | 1.354 (2) | C11X—H11C | 0.9800 |
N21A—H21A | 0.891 (16) | C2X—O21X | 1.232 (2) |
N21A—H22A | 0.865 (16) | C2X—C3X | 1.516 (3) |
N3A—C4A | 1.345 (2) | C3X—C4X | 1.518 (3) |
C4A—N41A | 1.347 (2) | C3X—H3X1 | 0.9900 |
C4A—C5A | 1.404 (2) | C3X—H3X2 | 0.9900 |
N41A—H41A | 0.893 (16) | C4X—C5X | 1.521 (3) |
N41A—H42A | 0.872 (16) | C4X—H4X1 | 0.9900 |
C5A—C6A | 1.372 (2) | C4X—H4X2 | 0.9900 |
C5A—H5A | 0.9500 | C5X—H5X1 | 0.9900 |
C6A—H6A | 0.9500 | C5X—H5X2 | 0.9900 |
N1B—C2B | 1.343 (2) | N1Y—C2Y | 1.333 (2) |
N1B—C6B | 1.349 (2) | N1Y—C11Y | 1.446 (2) |
C2B—N3B | 1.345 (2) | N1Y—C5Y | 1.450 (2) |
C2B—N21B | 1.346 (2) | C11Y—H11D | 0.9800 |
N21B—H21B | 0.899 (16) | C11Y—H11E | 0.9800 |
N21B—H22B | 0.880 (16) | C11Y—H11F | 0.9800 |
N3B—C4B | 1.346 (2) | C2Y—O21Y | 1.239 (2) |
C4B—N41B | 1.337 (2) | C2Y—C3Y | 1.500 (2) |
C4B—C5B | 1.405 (2) | C3Y—C4Y | 1.527 (3) |
N41B—H41B | 0.871 (16) | C3Y—H3Y1 | 0.9900 |
N41B—H42B | 0.895 (16) | C3Y—H3Y2 | 0.9900 |
C5B—C6B | 1.356 (3) | C4Y—C5Y | 1.533 (3) |
C5B—H5B | 0.9500 | C4Y—H4Y1 | 0.9900 |
C6B—H6B | 0.9500 | C4Y—H4Y2 | 0.9900 |
N1X—C2X | 1.328 (2) | C5Y—H5Y1 | 0.9900 |
N1X—C11X | 1.439 (3) | C5Y—H5Y2 | 0.9900 |
C6A—N1A—C2A | 114.83 (14) | O21X—C2X—C3X | 125.11 (17) |
N21A—C2A—N1A | 117.67 (14) | N1X—C2X—C3X | 108.88 (15) |
N21A—C2A—N3A | 116.13 (15) | C2X—C3X—C4X | 105.17 (17) |
N1A—C2A—N3A | 126.20 (15) | C2X—C3X—H3X1 | 110.7 |
C2A—N21A—H21A | 122.5 (15) | C4X—C3X—H3X1 | 110.7 |
C2A—N21A—H22A | 120.2 (15) | C2X—C3X—H3X2 | 110.7 |
H21A—N21A—H22A | 116 (2) | C4X—C3X—H3X2 | 110.7 |
C4A—N3A—C2A | 116.87 (15) | H3X1—C3X—H3X2 | 108.8 |
N3A—C4A—N41A | 116.71 (16) | C3X—C4X—C5X | 105.99 (16) |
N3A—C4A—C5A | 121.26 (15) | C3X—C4X—H4X1 | 110.5 |
N41A—C4A—C5A | 122.03 (15) | C5X—C4X—H4X1 | 110.5 |
C4A—N41A—H41A | 119.2 (15) | C3X—C4X—H4X2 | 110.5 |
C4A—N41A—H42A | 117.5 (15) | C5X—C4X—H4X2 | 110.5 |
H41A—N41A—H42A | 123 (2) | H4X1—C4X—H4X2 | 108.7 |
C6A—C5A—C4A | 116.63 (16) | N1X—C5X—C4X | 104.84 (15) |
C6A—C5A—H5A | 121.7 | N1X—C5X—H5X1 | 110.8 |
C4A—C5A—H5A | 121.7 | C4X—C5X—H5X1 | 110.8 |
N1A—C6A—C5A | 124.21 (16) | N1X—C5X—H5X2 | 110.8 |
N1A—C6A—H6A | 117.9 | C4X—C5X—H5X2 | 110.8 |
C5A—C6A—H6A | 117.9 | H5X1—C5X—H5X2 | 108.9 |
C2B—N1B—C6B | 114.35 (15) | C2Y—N1Y—C11Y | 123.35 (16) |
N1B—C2B—N3B | 126.50 (15) | C2Y—N1Y—C5Y | 115.05 (14) |
N1B—C2B—N21B | 115.76 (16) | C11Y—N1Y—C5Y | 121.55 (15) |
N3B—C2B—N21B | 117.74 (14) | N1Y—C11Y—H11D | 109.5 |
C2B—N21B—H21B | 121.7 (14) | N1Y—C11Y—H11E | 109.5 |
C2B—N21B—H22B | 118.8 (15) | H11D—C11Y—H11E | 109.5 |
H21B—N21B—H22B | 119 (2) | N1Y—C11Y—H11F | 109.5 |
C2B—N3B—C4B | 116.97 (14) | H11D—C11Y—H11F | 109.5 |
N41B—C4B—N3B | 117.59 (15) | H11E—C11Y—H11F | 109.5 |
N41B—C4B—C5B | 121.64 (15) | O21Y—C2Y—N1Y | 125.17 (16) |
N3B—C4B—C5B | 120.77 (16) | O21Y—C2Y—C3Y | 125.74 (15) |
C4B—N41B—H41B | 120.9 (16) | N1Y—C2Y—C3Y | 109.09 (15) |
C4B—N41B—H42B | 121.3 (16) | C2Y—C3Y—C4Y | 105.61 (14) |
H41B—N41B—H42B | 118 (2) | C2Y—C3Y—H3Y1 | 110.6 |
C6B—C5B—C4B | 116.68 (15) | C4Y—C3Y—H3Y1 | 110.6 |
C6B—C5B—H5B | 121.7 | C2Y—C3Y—H3Y2 | 110.6 |
C4B—C5B—H5B | 121.7 | C4Y—C3Y—H3Y2 | 110.6 |
N1B—C6B—C5B | 124.61 (15) | H3Y1—C3Y—H3Y2 | 108.7 |
N1B—C6B—H6B | 117.7 | C3Y—C4Y—C5Y | 105.85 (15) |
C5B—C6B—H6B | 117.7 | C3Y—C4Y—H4Y1 | 110.6 |
C2X—N1X—C11X | 123.56 (17) | C5Y—C4Y—H4Y1 | 110.6 |
C2X—N1X—C5X | 114.72 (18) | C3Y—C4Y—H4Y2 | 110.6 |
C11X—N1X—C5X | 121.71 (17) | C5Y—C4Y—H4Y2 | 110.6 |
N1X—C11X—H11A | 109.5 | H4Y1—C4Y—H4Y2 | 108.7 |
N1X—C11X—H11B | 109.5 | N1Y—C5Y—C4Y | 104.28 (14) |
H11A—C11X—H11B | 109.5 | N1Y—C5Y—H5Y1 | 110.9 |
N1X—C11X—H11C | 109.5 | C4Y—C5Y—H5Y1 | 110.9 |
H11A—C11X—H11C | 109.5 | N1Y—C5Y—H5Y2 | 110.9 |
H11B—C11X—H11C | 109.5 | C4Y—C5Y—H5Y2 | 110.9 |
O21X—C2X—N1X | 126.01 (19) | H5Y1—C5Y—H5Y2 | 108.9 |
C6A—N1A—C2A—N21A | 179.82 (15) | C11X—N1X—C2X—O21X | −0.6 (3) |
C6A—N1A—C2A—N3A | −1.0 (2) | C5X—N1X—C2X—O21X | 179.19 (18) |
N21A—C2A—N3A—C4A | −179.73 (15) | C11X—N1X—C2X—C3X | 179.55 (18) |
N1A—C2A—N3A—C4A | 1.1 (2) | C5X—N1X—C2X—C3X | −0.6 (2) |
C2A—N3A—C4A—N41A | 179.31 (15) | O21X—C2X—C3X—C4X | 176.81 (18) |
C2A—N3A—C4A—C5A | −0.3 (2) | N1X—C2X—C3X—C4X | −3.4 (2) |
N3A—C4A—C5A—C6A | −0.4 (2) | C2X—C3X—C4X—C5X | 5.8 (2) |
N41A—C4A—C5A—C6A | 179.97 (16) | C2X—N1X—C5X—C4X | 4.3 (2) |
C2A—N1A—C6A—C5A | 0.2 (2) | C11X—N1X—C5X—C4X | −175.84 (18) |
C4A—C5A—C6A—N1A | 0.5 (3) | C3X—C4X—C5X—N1X | −6.1 (2) |
C6B—N1B—C2B—N3B | −3.4 (3) | C11Y—N1Y—C2Y—O21Y | −0.8 (3) |
C6B—N1B—C2B—N21B | 177.51 (16) | C5Y—N1Y—C2Y—O21Y | 176.51 (16) |
N1B—C2B—N3B—C4B | 2.0 (3) | C11Y—N1Y—C2Y—C3Y | 179.63 (15) |
N21B—C2B—N3B—C4B | −178.87 (15) | C5Y—N1Y—C2Y—C3Y | −3.01 (19) |
C2B—N3B—C4B—N41B | −177.74 (16) | O21Y—C2Y—C3Y—C4Y | −178.53 (17) |
C2B—N3B—C4B—C5B | 1.5 (2) | N1Y—C2Y—C3Y—C4Y | 0.99 (19) |
N41B—C4B—C5B—C6B | 175.99 (18) | C2Y—C3Y—C4Y—C5Y | 1.15 (19) |
N3B—C4B—C5B—C6B | −3.2 (3) | C2Y—N1Y—C5Y—C4Y | 3.65 (19) |
C2B—N1B—C6B—C5B | 1.3 (3) | C11Y—N1Y—C5Y—C4Y | −178.94 (15) |
C4B—C5B—C6B—N1B | 1.7 (3) | C3Y—C4Y—C5Y—N1Y | −2.70 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N3Bi | 0.89 (2) | 2.09 (2) | 2.976 (2) | 175 (2) |
N21A—H22A···N1B | 0.87 (2) | 2.10 (2) | 2.961 (2) | 174 (2) |
N41A—H41A···O21X | 0.89 (2) | 2.11 (2) | 2.983 (2) | 166 (2) |
N41A—H42A···O21Yii | 0.87 (2) | 2.16 (2) | 2.9610 (19) | 152 (2) |
N21B—H21B···N3A | 0.90 (2) | 2.22 (2) | 3.109 (2) | 172 (2) |
N21B—H22B···O21X | 0.88 (2) | 2.22 (2) | 2.8344 (19) | 127 (2) |
N41B—H41B···N1Aiii | 0.87 (2) | 2.32 (2) | 3.186 (2) | 177 (2) |
N41B—H42B···O21Y | 0.90 (2) | 2.11 (2) | 2.995 (2) | 170 (2) |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+3/2, z−1/2; (iii) x−1/2, −y+3/2, z−1/2. |
C4H7N4+·C4H3N2O3− | F(000) = 496 |
Mr = 238.22 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.6822 (7) Å | Cell parameters from 5705 reflections |
b = 15.948 (3) Å | θ = 3.8–26.2° |
c = 13.514 (2) Å | µ = 0.12 mm−1 |
β = 90.240 (13)° | T = 173 K |
V = 1009.1 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.10 × 0.08 mm |
Stoe IPDS II two-circle diffractometer | 1460 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.102 |
ω scans | θmax = 25.9°, θmin = 3.8° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −5→5 |
Tmin = 0.619, Tmax = 1.000 | k = −19→18 |
7860 measured reflections | l = −16→16 |
1944 independent reflections |
Refinement on F2 | 7 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
1944 reflections | Δρmax = 0.23 e Å−3 |
176 parameters | Δρmin = −0.25 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.2689 (7) | 0.42819 (16) | 0.44519 (19) | 0.0169 (6) | |
H1A | 0.222 (8) | 0.4549 (18) | 0.4994 (19) | 0.020* | |
C2A | 0.4877 (8) | 0.37155 (17) | 0.4487 (2) | 0.0163 (7) | |
O21A | 0.6357 (6) | 0.35884 (12) | 0.52379 (16) | 0.0223 (5) | |
N3A | 0.5357 (7) | 0.32902 (14) | 0.36289 (19) | 0.0178 (6) | |
H3A | 0.671 (6) | 0.2912 (16) | 0.370 (3) | 0.021* | |
C4A | 0.3840 (8) | 0.34092 (18) | 0.2746 (2) | 0.0183 (7) | |
O41A | 0.4528 (6) | 0.29552 (13) | 0.20251 (16) | 0.0258 (6) | |
C5A | 0.1670 (8) | 0.40157 (19) | 0.2754 (2) | 0.0183 (7) | |
H5A | 0.0632 | 0.4133 | 0.2164 | 0.022* | |
C6A | 0.1031 (7) | 0.44454 (16) | 0.3619 (2) | 0.0160 (7) | |
O61A | −0.0959 (5) | 0.49829 (11) | 0.37188 (16) | 0.0189 (5) | |
N1B | 1.1948 (7) | 0.08187 (16) | 0.2962 (2) | 0.0214 (7) | |
H1B | 1.208 (9) | 0.0502 (19) | 0.2416 (19) | 0.026* | |
C2B | 1.0026 (7) | 0.14533 (16) | 0.2973 (2) | 0.0176 (7) | |
N21B | 0.8403 (7) | 0.15692 (17) | 0.2181 (2) | 0.0236 (7) | |
H22B | 0.709 (7) | 0.1965 (18) | 0.220 (3) | 0.028* | |
H21B | 0.870 (9) | 0.1269 (18) | 0.1649 (18) | 0.028* | |
N3B | 0.9683 (6) | 0.19526 (14) | 0.37599 (19) | 0.0186 (6) | |
C4B | 1.1312 (8) | 0.18093 (17) | 0.4576 (2) | 0.0176 (7) | |
N41B | 1.0845 (7) | 0.22811 (15) | 0.53618 (19) | 0.0233 (7) | |
H41B | 0.970 (7) | 0.2709 (16) | 0.533 (3) | 0.028* | |
H42B | 1.176 (8) | 0.221 (2) | 0.5918 (19) | 0.028* | |
C5B | 1.3433 (8) | 0.11656 (17) | 0.4593 (2) | 0.0234 (7) | |
H5B | 1.4624 | 0.1078 | 0.5155 | 0.028* | |
C6B | 1.3665 (8) | 0.06878 (17) | 0.3771 (3) | 0.0234 (7) | |
H6B | 1.5048 | 0.0252 | 0.3754 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0209 (16) | 0.0194 (13) | 0.0105 (12) | 0.0029 (11) | 0.0017 (11) | −0.0022 (10) |
C2A | 0.0199 (18) | 0.0155 (13) | 0.0133 (15) | −0.0058 (13) | −0.0004 (14) | 0.0031 (10) |
O21A | 0.0251 (14) | 0.0274 (11) | 0.0144 (11) | 0.0042 (10) | −0.0093 (12) | −0.0032 (9) |
N3A | 0.0196 (16) | 0.0188 (11) | 0.0150 (12) | 0.0041 (11) | −0.0056 (13) | −0.0028 (10) |
C4A | 0.0201 (18) | 0.0223 (15) | 0.0126 (14) | −0.0020 (14) | −0.0039 (14) | 0.0001 (11) |
O41A | 0.0294 (15) | 0.0325 (11) | 0.0155 (10) | 0.0109 (11) | −0.0088 (11) | −0.0091 (9) |
C5A | 0.0174 (18) | 0.0217 (14) | 0.0157 (14) | 0.0026 (13) | −0.0033 (15) | −0.0006 (12) |
C6A | 0.0166 (18) | 0.0135 (12) | 0.0180 (15) | −0.0017 (12) | −0.0032 (15) | 0.0025 (11) |
O61A | 0.0240 (13) | 0.0172 (9) | 0.0154 (10) | 0.0052 (10) | −0.0018 (11) | 0.0010 (8) |
N1B | 0.0271 (18) | 0.0201 (13) | 0.0170 (14) | 0.0005 (12) | −0.0013 (13) | −0.0023 (11) |
C2B | 0.0211 (19) | 0.0165 (13) | 0.0153 (14) | −0.0017 (13) | 0.0025 (15) | 0.0003 (11) |
N21B | 0.0296 (19) | 0.0264 (14) | 0.0146 (13) | 0.0056 (13) | −0.0050 (14) | −0.0051 (11) |
N3B | 0.0207 (17) | 0.0207 (12) | 0.0143 (12) | −0.0012 (11) | −0.0008 (14) | −0.0002 (11) |
C4B | 0.0206 (19) | 0.0176 (13) | 0.0146 (15) | −0.0060 (13) | −0.0034 (15) | 0.0049 (11) |
N41B | 0.0323 (19) | 0.0226 (13) | 0.0150 (12) | 0.0048 (12) | −0.0071 (14) | −0.0002 (11) |
C5B | 0.0254 (19) | 0.0235 (15) | 0.0212 (17) | 0.0002 (15) | −0.0058 (17) | 0.0048 (13) |
C6B | 0.0218 (18) | 0.0213 (14) | 0.0269 (17) | 0.0048 (14) | −0.0046 (18) | 0.0035 (14) |
N1A—C2A | 1.366 (4) | N1B—H1B | 0.896 (18) |
N1A—C6A | 1.390 (4) | C2B—N21B | 1.323 (4) |
N1A—H1A | 0.878 (18) | C2B—N3B | 1.339 (4) |
C2A—O21A | 1.243 (4) | N21B—H22B | 0.881 (19) |
C2A—N3A | 1.363 (4) | N21B—H21B | 0.875 (18) |
N3A—C4A | 1.399 (4) | N3B—C4B | 1.358 (4) |
N3A—H3A | 0.879 (18) | C4B—N41B | 1.320 (4) |
C4A—O41A | 1.257 (4) | C4B—C5B | 1.428 (5) |
C4A—C5A | 1.403 (5) | N41B—H41B | 0.868 (18) |
C5A—C6A | 1.389 (4) | N41B—H42B | 0.870 (19) |
C5A—H5A | 0.9500 | C5B—C6B | 1.352 (5) |
C6A—O61A | 1.274 (4) | C5B—H5B | 0.9500 |
N1B—C2B | 1.354 (4) | C6B—H6B | 0.9500 |
N1B—C6B | 1.371 (5) | ||
C2A—N1A—C6A | 124.7 (3) | C6B—N1B—H1B | 122 (2) |
C2A—N1A—H1A | 119 (2) | N21B—C2B—N3B | 119.3 (3) |
C6A—N1A—H1A | 116 (2) | N21B—C2B—N1B | 118.3 (3) |
O21A—C2A—N3A | 121.3 (3) | N3B—C2B—N1B | 122.3 (3) |
O21A—C2A—N1A | 123.5 (3) | C2B—N21B—H22B | 119 (2) |
N3A—C2A—N1A | 115.2 (3) | C2B—N21B—H21B | 120 (3) |
C2A—N3A—C4A | 125.0 (3) | H22B—N21B—H21B | 122 (4) |
C2A—N3A—H3A | 112 (2) | C2B—N3B—C4B | 118.5 (3) |
C4A—N3A—H3A | 123 (2) | N41B—C4B—N3B | 117.6 (3) |
O41A—C4A—N3A | 116.9 (3) | N41B—C4B—C5B | 121.0 (3) |
O41A—C4A—C5A | 126.2 (3) | N3B—C4B—C5B | 121.5 (3) |
N3A—C4A—C5A | 116.9 (3) | C4B—N41B—H41B | 121 (2) |
C6A—C5A—C4A | 120.3 (3) | C4B—N41B—H42B | 123 (2) |
C6A—C5A—H5A | 119.8 | H41B—N41B—H42B | 116 (3) |
C4A—C5A—H5A | 119.8 | C6B—C5B—C4B | 116.8 (3) |
O61A—C6A—C5A | 125.6 (3) | C6B—C5B—H5B | 121.6 |
O61A—C6A—N1A | 116.5 (3) | C4B—C5B—H5B | 121.6 |
C5A—C6A—N1A | 117.9 (3) | C5B—C6B—N1B | 121.4 (3) |
C2B—N1B—C6B | 119.5 (3) | C5B—C6B—H6B | 119.3 |
C2B—N1B—H1B | 119 (2) | N1B—C6B—H6B | 119.3 |
C6A—N1A—C2A—O21A | 179.0 (3) | C2A—N1A—C6A—C5A | −1.3 (4) |
C6A—N1A—C2A—N3A | −0.8 (4) | C6B—N1B—C2B—N21B | 179.7 (3) |
O21A—C2A—N3A—C4A | −178.4 (3) | C6B—N1B—C2B—N3B | −1.6 (5) |
N1A—C2A—N3A—C4A | 1.4 (4) | N21B—C2B—N3B—C4B | 178.2 (3) |
C2A—N3A—C4A—O41A | −179.0 (3) | N1B—C2B—N3B—C4B | −0.6 (5) |
C2A—N3A—C4A—C5A | 0.2 (5) | C2B—N3B—C4B—N41B | −176.7 (3) |
O41A—C4A—C5A—C6A | 176.7 (3) | C2B—N3B—C4B—C5B | 2.6 (5) |
N3A—C4A—C5A—C6A | −2.4 (5) | N41B—C4B—C5B—C6B | 176.9 (3) |
C4A—C5A—C6A—O61A | −177.1 (3) | N3B—C4B—C5B—C6B | −2.4 (5) |
C4A—C5A—C6A—N1A | 2.9 (5) | C4B—C5B—C6B—N1B | 0.2 (5) |
C2A—N1A—C6A—O61A | 178.8 (3) | C2B—N1B—C6B—C5B | 1.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O61Ai | 0.88 (2) | 1.98 (2) | 2.856 (3) | 173 (3) |
N3A—H3A···N3B | 0.88 (2) | 2.07 (2) | 2.946 (4) | 175 (3) |
N1B—H1B···O61Aii | 0.90 (2) | 1.82 (2) | 2.672 (3) | 159 (4) |
N21B—H22B···O41A | 0.88 (2) | 2.00 (2) | 2.867 (4) | 169 (4) |
N21B—H21B···O21Aiii | 0.88 (2) | 2.21 (3) | 2.803 (3) | 125 (3) |
N21B—H21B···O61Aii | 0.88 (2) | 2.36 (3) | 3.053 (3) | 136 (3) |
N41B—H41B···O21A | 0.87 (2) | 2.11 (2) | 2.965 (4) | 170 (3) |
N41B—H42B···O41Aiv | 0.87 (2) | 1.99 (2) | 2.852 (4) | 169 (4) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z+1/2. |
C4H7N4+·C4H3N2O2S−·2C3H7NO | F(000) = 848 |
Mr = 400.47 | Dx = 1.334 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0115 (9) Å | Cell parameters from 20088 reflections |
b = 19.2213 (14) Å | θ = 3.3–26.3° |
c = 12.9531 (13) Å | µ = 0.20 mm−1 |
β = 90.230 (8)° | T = 173 K |
V = 1994.7 (3) Å3 | Plate, yellow |
Z = 4 | 0.39 × 0.28 × 0.15 mm |
Stoe IPDS II two-circle diffractometer | 3134 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.048 |
ω scans | θmax = 25.9°, θmin = 3.3° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.532, Tmax = 1.000 | k = −23→19 |
14897 measured reflections | l = −15→15 |
3834 independent reflections |
Refinement on F2 | 114 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.7095P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.040 |
3834 reflections | Δρmax = 0.34 e Å−3 |
282 parameters | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The used target distances were 1.23 (1) Å for d(C1Y,O11Y) and d(C1Y',O11Y), 1.32 (1) Å for d(C1Y,N2Y) and d(C1Y',N2Y), 1.44 (1) Å for d(N2Y,C3Y) and d(N2Y,C4Y), 1.44 (1) Å for d(N2Y,C3Y') and d(N2Y,C4Y'), 2.26 (2) Å for d(O11Y,N2Y), 2.41 (2) Å for d(C1Y,C3Y) and d(C1Y',C3Y'), 2.47 (2) Å for d(C3Y,C4Y) and d(C3Y',C4Y'), 2.41 (2) Å for d(C1Y,C4Y) and d(C1Y',C4Y'). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.84760 (19) | 0.06939 (7) | 0.46165 (11) | 0.0250 (3) | |
H1A | 0.887 (2) | 0.0500 (10) | 0.5165 (13) | 0.030* | |
C2A | 0.7540 (2) | 0.12707 (9) | 0.47481 (13) | 0.0249 (4) | |
S21A | 0.69289 (7) | 0.15336 (3) | 0.59188 (3) | 0.03891 (16) | |
N3A | 0.71165 (18) | 0.16090 (7) | 0.38694 (10) | 0.0240 (3) | |
H3A | 0.658 (2) | 0.1997 (9) | 0.3925 (15) | 0.029* | |
C4A | 0.7587 (2) | 0.14054 (9) | 0.28742 (13) | 0.0246 (4) | |
O41A | 0.70990 (17) | 0.17795 (7) | 0.21384 (9) | 0.0340 (3) | |
C5A | 0.8541 (2) | 0.08030 (9) | 0.27958 (13) | 0.0259 (4) | |
H5A | 0.8861 | 0.0638 | 0.2134 | 0.031* | |
C6A | 0.9028 (2) | 0.04408 (8) | 0.36688 (12) | 0.0238 (4) | |
O61A | 0.99171 (16) | −0.01030 (6) | 0.36919 (9) | 0.0304 (3) | |
N1B | 0.47285 (19) | 0.40827 (8) | 0.30032 (11) | 0.0276 (3) | |
H1B | 0.484 (3) | 0.4335 (10) | 0.2430 (13) | 0.033* | |
C2B | 0.5347 (2) | 0.34282 (9) | 0.30336 (13) | 0.0249 (4) | |
N21B | 0.6095 (2) | 0.31781 (9) | 0.22048 (12) | 0.0338 (4) | |
H21B | 0.604 (3) | 0.3400 (11) | 0.1640 (14) | 0.041* | |
H22B | 0.639 (3) | 0.2730 (9) | 0.2203 (16) | 0.041* | |
N3B | 0.52452 (18) | 0.30284 (7) | 0.38770 (10) | 0.0243 (3) | |
C4B | 0.4433 (2) | 0.32879 (9) | 0.47022 (13) | 0.0247 (4) | |
N41B | 0.4331 (2) | 0.28982 (8) | 0.55359 (12) | 0.0341 (4) | |
H41B | 0.483 (3) | 0.2483 (9) | 0.5548 (16) | 0.041* | |
H42B | 0.368 (2) | 0.3027 (12) | 0.6052 (14) | 0.041* | |
C5B | 0.3710 (2) | 0.39653 (9) | 0.46897 (13) | 0.0283 (4) | |
H5B | 0.3113 | 0.4139 | 0.5267 | 0.034* | |
C6B | 0.3906 (2) | 0.43480 (9) | 0.38325 (13) | 0.0289 (4) | |
H6B | 0.3467 | 0.4807 | 0.3804 | 0.035* | |
C1X | 0.7561 (3) | 0.38746 (12) | −0.02899 (17) | 0.0453 (5) | |
H1X | 0.7859 | 0.4241 | 0.0167 | 0.054* | |
O11X | 0.6752 (2) | 0.34008 (9) | 0.00683 (12) | 0.0541 (4) | |
N2X | 0.8070 (2) | 0.39296 (9) | −0.12613 (13) | 0.0420 (4) | |
C3X | 0.7669 (3) | 0.34004 (14) | −0.20127 (18) | 0.0550 (6) | |
H3X1 | 0.7095 | 0.3014 | −0.1671 | 0.082* | |
H3X2 | 0.8700 | 0.3230 | −0.2330 | 0.082* | |
H3X3 | 0.6942 | 0.3598 | −0.2547 | 0.082* | |
C4X | 0.8879 (3) | 0.45554 (14) | −0.1627 (2) | 0.0636 (7) | |
H4X1 | 0.8099 | 0.4820 | −0.2060 | 0.095* | |
H4X2 | 0.9863 | 0.4429 | −0.2034 | 0.095* | |
H4X3 | 0.9223 | 0.4840 | −0.1036 | 0.095* | |
O11Y | 0.2006 (3) | 0.57184 (11) | 0.44309 (18) | 0.0870 (7) | |
N2Y | 0.0745 (2) | 0.62769 (9) | 0.57514 (14) | 0.0425 (4) | |
C1Y | 0.1367 (4) | 0.62427 (14) | 0.4809 (2) | 0.0565 (8) | 0.902 (4) |
H1YA | 0.1318 | 0.6650 | 0.4395 | 0.068* | 0.902 (4) |
C3Y | 0.0797 (4) | 0.56662 (14) | 0.6413 (2) | 0.0602 (8) | 0.902 (4) |
H3YA | 0.0943 | 0.5812 | 0.7133 | 0.090* | 0.902 (4) |
H3YB | 0.1733 | 0.5368 | 0.6210 | 0.090* | 0.902 (4) |
H3YC | −0.0250 | 0.5407 | 0.6342 | 0.090* | 0.902 (4) |
C4Y | 0.0042 (3) | 0.69037 (14) | 0.6167 (2) | 0.0546 (8) | 0.902 (4) |
H4YA | −0.1104 | 0.6814 | 0.6393 | 0.082* | 0.902 (4) |
H4YB | 0.0035 | 0.7266 | 0.5635 | 0.082* | 0.902 (4) |
H4YC | 0.0714 | 0.7059 | 0.6757 | 0.082* | 0.902 (4) |
C1Y' | 0.146 (4) | 0.5708 (8) | 0.5355 (12) | 0.087 (8)* | 0.098 (4) |
H1YB | 0.1550 | 0.5297 | 0.5759 | 0.104* | 0.098 (4) |
C3Y' | 0.065 (3) | 0.6836 (9) | 0.4975 (14) | 0.059 (7)* | 0.098 (4) |
H3YD | 0.0123 | 0.7248 | 0.5282 | 0.089* | 0.098 (4) |
H3YE | 0.1774 | 0.6955 | 0.4742 | 0.089* | 0.098 (4) |
H3YF | −0.0022 | 0.6678 | 0.4385 | 0.089* | 0.098 (4) |
C4Y' | 0.008 (4) | 0.6444 (13) | 0.6742 (12) | 0.069 (8)* | 0.098 (4) |
H4YD | −0.0338 | 0.6923 | 0.6736 | 0.103* | 0.098 (4) |
H4YE | −0.0830 | 0.6124 | 0.6905 | 0.103* | 0.098 (4) |
H4YF | 0.0964 | 0.6400 | 0.7265 | 0.103* | 0.098 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0344 (8) | 0.0210 (7) | 0.0197 (7) | 0.0058 (6) | −0.0031 (6) | −0.0008 (6) |
C2A | 0.0293 (9) | 0.0225 (8) | 0.0229 (8) | 0.0007 (7) | −0.0005 (7) | −0.0008 (6) |
S21A | 0.0580 (3) | 0.0383 (3) | 0.0205 (2) | 0.0229 (2) | 0.0014 (2) | −0.00117 (19) |
N3A | 0.0305 (8) | 0.0199 (7) | 0.0217 (7) | 0.0052 (6) | 0.0021 (6) | 0.0000 (6) |
C4A | 0.0275 (9) | 0.0225 (8) | 0.0237 (8) | −0.0015 (7) | 0.0024 (6) | 0.0011 (6) |
O41A | 0.0462 (8) | 0.0326 (7) | 0.0233 (6) | 0.0123 (6) | 0.0063 (5) | 0.0072 (5) |
C5A | 0.0318 (9) | 0.0257 (9) | 0.0203 (8) | 0.0018 (7) | 0.0015 (7) | −0.0022 (6) |
C6A | 0.0266 (8) | 0.0199 (8) | 0.0249 (8) | −0.0015 (7) | −0.0014 (7) | −0.0049 (6) |
O61A | 0.0422 (7) | 0.0231 (6) | 0.0257 (6) | 0.0106 (5) | −0.0039 (5) | −0.0051 (5) |
N1B | 0.0359 (8) | 0.0220 (7) | 0.0250 (7) | 0.0009 (6) | −0.0017 (6) | 0.0065 (6) |
C2B | 0.0274 (9) | 0.0227 (8) | 0.0245 (8) | −0.0009 (7) | −0.0024 (7) | 0.0034 (7) |
N21B | 0.0477 (10) | 0.0317 (8) | 0.0219 (8) | 0.0092 (7) | 0.0047 (7) | 0.0082 (6) |
N3B | 0.0305 (8) | 0.0212 (7) | 0.0212 (7) | 0.0017 (6) | 0.0017 (6) | 0.0033 (5) |
C4B | 0.0265 (9) | 0.0239 (9) | 0.0235 (8) | −0.0020 (7) | −0.0013 (7) | −0.0002 (6) |
N41B | 0.0507 (10) | 0.0259 (8) | 0.0257 (8) | 0.0082 (7) | 0.0114 (7) | 0.0047 (6) |
C5B | 0.0330 (10) | 0.0261 (9) | 0.0259 (9) | 0.0031 (7) | −0.0017 (7) | −0.0026 (7) |
C6B | 0.0335 (10) | 0.0219 (8) | 0.0312 (9) | 0.0034 (7) | −0.0055 (7) | −0.0006 (7) |
C1X | 0.0461 (12) | 0.0441 (12) | 0.0457 (12) | 0.0153 (10) | 0.0051 (10) | 0.0086 (10) |
O11X | 0.0689 (11) | 0.0520 (10) | 0.0415 (8) | 0.0114 (8) | 0.0155 (8) | 0.0144 (7) |
N2X | 0.0403 (10) | 0.0424 (10) | 0.0435 (10) | 0.0089 (8) | 0.0092 (8) | 0.0147 (8) |
C3X | 0.0560 (14) | 0.0669 (16) | 0.0422 (12) | 0.0088 (12) | 0.0088 (11) | 0.0061 (11) |
C4X | 0.0484 (14) | 0.0516 (15) | 0.091 (2) | 0.0097 (11) | 0.0206 (13) | 0.0292 (14) |
O11Y | 0.0957 (16) | 0.0649 (13) | 0.1006 (17) | 0.0171 (12) | 0.0210 (13) | −0.0269 (12) |
N2Y | 0.0417 (10) | 0.0312 (9) | 0.0545 (11) | −0.0006 (8) | −0.0005 (8) | −0.0008 (8) |
C1Y | 0.0630 (17) | 0.0415 (15) | 0.0651 (17) | 0.0014 (13) | 0.0042 (14) | 0.0002 (13) |
C3Y | 0.0608 (18) | 0.0425 (15) | 0.077 (2) | −0.0091 (13) | −0.0137 (15) | 0.0113 (13) |
C4Y | 0.0458 (15) | 0.0431 (15) | 0.0750 (19) | 0.0024 (11) | −0.0063 (13) | −0.0164 (13) |
N1A—C2A | 1.350 (2) | N2X—C3X | 1.443 (3) |
N1A—C6A | 1.394 (2) | N2X—C4X | 1.447 (3) |
N1A—H1A | 0.862 (15) | C3X—H3X1 | 0.9800 |
C2A—N3A | 1.353 (2) | C3X—H3X2 | 0.9800 |
C2A—S21A | 1.6736 (17) | C3X—H3X3 | 0.9800 |
N3A—C4A | 1.400 (2) | C4X—H4X1 | 0.9800 |
N3A—H3A | 0.864 (15) | C4X—H4X2 | 0.9800 |
C4A—O41A | 1.255 (2) | C4X—H4X3 | 0.9800 |
C4A—C5A | 1.391 (2) | O11Y—C1Y | 1.233 (3) |
C5A—C6A | 1.383 (2) | O11Y—C1Y' | 1.277 (10) |
C5A—H5A | 0.9500 | N2Y—C1Y | 1.322 (3) |
C6A—O61A | 1.265 (2) | N2Y—C1Y' | 1.337 (9) |
N1B—C2B | 1.352 (2) | N2Y—C4Y' | 1.427 (9) |
N1B—C6B | 1.362 (2) | N2Y—C4Y | 1.436 (3) |
N1B—H1B | 0.892 (15) | N2Y—C3Y | 1.454 (3) |
C2B—N21B | 1.322 (2) | N2Y—C3Y' | 1.475 (9) |
C2B—N3B | 1.339 (2) | C1Y—H1YA | 0.9500 |
N21B—H21B | 0.848 (16) | C3Y—H3YA | 0.9800 |
N21B—H22B | 0.894 (16) | C3Y—H3YB | 0.9800 |
N3B—C4B | 1.349 (2) | C3Y—H3YC | 0.9800 |
C4B—N41B | 1.317 (2) | C4Y—H4YA | 0.9800 |
C4B—C5B | 1.425 (2) | C4Y—H4YB | 0.9800 |
N41B—H41B | 0.892 (16) | C4Y—H4YC | 0.9800 |
N41B—H42B | 0.885 (16) | C1Y'—H1YB | 0.9500 |
C5B—C6B | 1.342 (2) | C3Y'—H3YD | 0.9800 |
C5B—H5B | 0.9500 | C3Y'—H3YE | 0.9800 |
C6B—H6B | 0.9500 | C3Y'—H3YF | 0.9800 |
C1X—O11X | 1.211 (3) | C4Y'—H4YD | 0.9800 |
C1X—N2X | 1.328 (3) | C4Y'—H4YE | 0.9800 |
C1X—H1X | 0.9500 | C4Y'—H4YF | 0.9800 |
C2A—N1A—C6A | 125.19 (14) | N2X—C3X—H3X2 | 109.5 |
C2A—N1A—H1A | 116.9 (13) | H3X1—C3X—H3X2 | 109.5 |
C6A—N1A—H1A | 117.3 (13) | N2X—C3X—H3X3 | 109.5 |
N1A—C2A—N3A | 115.23 (15) | H3X1—C3X—H3X3 | 109.5 |
N1A—C2A—S21A | 121.82 (13) | H3X2—C3X—H3X3 | 109.5 |
N3A—C2A—S21A | 122.94 (13) | N2X—C4X—H4X1 | 109.5 |
C2A—N3A—C4A | 124.92 (15) | N2X—C4X—H4X2 | 109.5 |
C2A—N3A—H3A | 117.9 (13) | H4X1—C4X—H4X2 | 109.5 |
C4A—N3A—H3A | 117.0 (13) | N2X—C4X—H4X3 | 109.5 |
O41A—C4A—C5A | 126.22 (16) | H4X1—C4X—H4X3 | 109.5 |
O41A—C4A—N3A | 117.05 (15) | H4X2—C4X—H4X3 | 109.5 |
C5A—C4A—N3A | 116.73 (15) | C1Y'—N2Y—C4Y' | 133.6 (11) |
C6A—C5A—C4A | 120.84 (15) | C1Y—N2Y—C4Y | 122.5 (2) |
C6A—C5A—H5A | 119.6 | C1Y—N2Y—C3Y | 119.6 (2) |
C4A—C5A—H5A | 119.6 | C4Y—N2Y—C3Y | 117.8 (2) |
O61A—C6A—C5A | 126.33 (15) | C1Y'—N2Y—C3Y' | 110.9 (9) |
O61A—C6A—N1A | 116.62 (14) | C4Y'—N2Y—C3Y' | 115.5 (11) |
C5A—C6A—N1A | 117.04 (15) | O11Y—C1Y—N2Y | 124.5 (3) |
C2B—N1B—C6B | 120.25 (15) | O11Y—C1Y—H1YA | 117.8 |
C2B—N1B—H1B | 119.5 (13) | N2Y—C1Y—H1YA | 117.8 |
C6B—N1B—H1B | 120.2 (13) | N2Y—C3Y—H3YA | 109.5 |
N21B—C2B—N3B | 118.90 (16) | N2Y—C3Y—H3YB | 109.5 |
N21B—C2B—N1B | 118.80 (15) | H3YA—C3Y—H3YB | 109.5 |
N3B—C2B—N1B | 122.30 (15) | N2Y—C3Y—H3YC | 109.5 |
C2B—N21B—H21B | 119.7 (15) | H3YA—C3Y—H3YC | 109.5 |
C2B—N21B—H22B | 118.3 (14) | H3YB—C3Y—H3YC | 109.5 |
H21B—N21B—H22B | 120 (2) | N2Y—C4Y—H4YA | 109.5 |
C2B—N3B—C4B | 117.74 (15) | N2Y—C4Y—H4YB | 109.5 |
N41B—C4B—N3B | 118.10 (16) | H4YA—C4Y—H4YB | 109.5 |
N41B—C4B—C5B | 120.15 (16) | N2Y—C4Y—H4YC | 109.5 |
N3B—C4B—C5B | 121.74 (15) | H4YA—C4Y—H4YC | 109.5 |
C4B—N41B—H41B | 119.6 (14) | H4YB—C4Y—H4YC | 109.5 |
C4B—N41B—H42B | 119.9 (15) | O11Y—C1Y'—N2Y | 119.8 (10) |
H41B—N41B—H42B | 120 (2) | O11Y—C1Y'—H1YB | 120.1 |
C6B—C5B—C4B | 117.49 (16) | N2Y—C1Y'—H1YB | 120.1 |
C6B—C5B—H5B | 121.3 | N2Y—C3Y'—H3YD | 109.5 |
C4B—C5B—H5B | 121.3 | N2Y—C3Y'—H3YE | 109.5 |
C5B—C6B—N1B | 120.40 (16) | H3YD—C3Y'—H3YE | 109.5 |
C5B—C6B—H6B | 119.8 | N2Y—C3Y'—H3YF | 109.5 |
N1B—C6B—H6B | 119.8 | H3YD—C3Y'—H3YF | 109.5 |
O11X—C1X—N2X | 126.1 (2) | H3YE—C3Y'—H3YF | 109.5 |
O11X—C1X—H1X | 116.9 | N2Y—C4Y'—H4YD | 109.5 |
N2X—C1X—H1X | 116.9 | N2Y—C4Y'—H4YE | 109.5 |
C1X—N2X—C3X | 120.97 (19) | H4YD—C4Y'—H4YE | 109.5 |
C1X—N2X—C4X | 121.1 (2) | N2Y—C4Y'—H4YF | 109.5 |
C3X—N2X—C4X | 117.6 (2) | H4YD—C4Y'—H4YF | 109.5 |
N2X—C3X—H3X1 | 109.5 | H4YE—C4Y'—H4YF | 109.5 |
C6A—N1A—C2A—N3A | 0.9 (2) | N21B—C2B—N3B—C4B | −178.11 (16) |
C6A—N1A—C2A—S21A | 179.78 (13) | N1B—C2B—N3B—C4B | 2.7 (2) |
N1A—C2A—N3A—C4A | −0.5 (2) | C2B—N3B—C4B—N41B | −179.85 (16) |
S21A—C2A—N3A—C4A | −179.45 (13) | C2B—N3B—C4B—C5B | −0.4 (2) |
C2A—N3A—C4A—O41A | −179.52 (16) | N41B—C4B—C5B—C6B | 177.64 (17) |
C2A—N3A—C4A—C5A | 1.0 (2) | N3B—C4B—C5B—C6B | −1.8 (3) |
O41A—C4A—C5A—C6A | 178.82 (17) | C4B—C5B—C6B—N1B | 1.7 (3) |
N3A—C4A—C5A—C6A | −1.8 (2) | C2B—N1B—C6B—C5B | 0.5 (3) |
C4A—C5A—C6A—O61A | −178.62 (17) | O11X—C1X—N2X—C3X | 0.3 (3) |
C4A—C5A—C6A—N1A | 2.1 (2) | O11X—C1X—N2X—C4X | 173.4 (2) |
C2A—N1A—C6A—O61A | 178.99 (16) | C4Y—N2Y—C1Y—O11Y | 178.7 (3) |
C2A—N1A—C6A—C5A | −1.6 (3) | C3Y—N2Y—C1Y—O11Y | 0.1 (4) |
C6B—N1B—C2B—N21B | 177.99 (16) | C4Y'—N2Y—C1Y'—O11Y | −177 (2) |
C6B—N1B—C2B—N3B | −2.8 (3) | C3Y'—N2Y—C1Y'—O11Y | 3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···N3B | 0.86 (2) | 2.25 (2) | 3.113 (2) | 173 (2) |
N1A—H1A···O61Ai | 0.86 (2) | 1.93 (2) | 2.7795 (19) | 171 (2) |
N1B—H1B···O61Aii | 0.89 (2) | 1.82 (2) | 2.7123 (18) | 177 (2) |
N21B—H21B···O11X | 0.85 (2) | 2.12 (2) | 2.851 (2) | 145 (2) |
N21B—H22B···O41A | 0.89 (2) | 1.92 (2) | 2.807 (2) | 177 (2) |
N41B—H41B···S21A | 0.89 (2) | 2.53 (2) | 3.3839 (17) | 161 (2) |
N41B—H42B···O41Aiii | 0.89 (2) | 1.93 (2) | 2.814 (2) | 173 (2) |
C6B—H6B···O11Y | 0.95 | 2.26 | 3.141 (3) | 154 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z+1/2. |
C4H7N4+·C4H3N2O2S−·2(C4H9NO) | F(000) = 912 |
Mr = 428.52 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8868 (12) Å | Cell parameters from 12893 reflections |
b = 17.2380 (14) Å | θ = 3.4–25.9° |
c = 12.8571 (14) Å | µ = 0.19 mm−1 |
β = 88.151 (9)° | T = 173 K |
V = 2190.1 (4) Å3 | Block, yellow |
Z = 4 | 0.18 × 0.11 × 0.08 mm |
Stoe IPDS II two-circle diffractometer | 2955 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.059 |
ω scans | θmax = 25.9°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −10→12 |
Tmin = 0.653, Tmax = 1.000 | k = −20→21 |
17989 measured reflections | l = −15→15 |
4205 independent reflections |
Refinement on F2 | 135 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
4205 reflections | Δρmax = 0.21 e Å−3 |
308 parameters | Δρmin = −0.19 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The used target distances were 1.52 (1) Å for d(C1X/Y,C2X/Y) and d(C31X/Y,C2X'/Y'), 1.25 (1) Å for d(C2X/Y,O21X/Y) and d(C2X'/Y',O21X/Y), 1.30 (1) Å for d(C2X/Y,N3X/Y) and d(C2X'/Y',N3X'/Y'), 1.47 (1) Å for d(N3X/Y,C31X/Y), d(N3X/Y,C32X/Y), d(N3X'/Y',C1X/Y) and d(N3X'/Y',C32X/Y), 2.42 (2) Å for d(O21X/Y,C1X/Y) and d(O21X/Y,C31X/Y), 2.23 (2) Å for d(O21X/Y,N3X/Y) and d(O21X/Y,N3X'/Y'), 2.41 (2) Å for d(C1X/Y,N3X/Y) and d(C31X/Y,N3X'/Y'), 2.41 (2) Å for d(C2X/Y,C31X/Y) and d(C2X'/Y',C1X/Y), 2.43 (2) Å for d(C2X/Y,C32X/Y) and d(C2X'/Y',C32X/Y), and 2.52 (2) Å for d(C31X/Y,C32X/Y) and d(C1X/Y,C32X/Y). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.88288 (18) | 0.07520 (10) | 0.45962 (12) | 0.0269 (4) | |
H1A | 0.908 (2) | 0.0492 (12) | 0.5114 (15) | 0.032* | |
C2A | 0.7891 (2) | 0.13066 (12) | 0.47308 (15) | 0.0263 (5) | |
S21A | 0.71829 (6) | 0.14897 (4) | 0.59124 (4) | 0.03585 (17) | |
N3A | 0.75454 (18) | 0.16903 (11) | 0.38638 (12) | 0.0281 (4) | |
H3A | 0.691 (2) | 0.2043 (12) | 0.3917 (17) | 0.034* | |
C4A | 0.8082 (2) | 0.15380 (13) | 0.28639 (14) | 0.0292 (5) | |
O41A | 0.76665 (16) | 0.19478 (10) | 0.21302 (10) | 0.0383 (4) | |
C5A | 0.9035 (2) | 0.09471 (13) | 0.27764 (15) | 0.0304 (5) | |
H5A | 0.9412 | 0.0816 | 0.2111 | 0.037* | |
C6A | 0.9442 (2) | 0.05460 (13) | 0.36475 (15) | 0.0279 (5) | |
O61A | 1.02988 (16) | 0.00038 (9) | 0.36625 (10) | 0.0346 (4) | |
N1B | 0.44262 (19) | 0.40463 (11) | 0.29932 (13) | 0.0305 (4) | |
H1B | 0.439 (2) | 0.4352 (12) | 0.2461 (15) | 0.037* | |
C2B | 0.5267 (2) | 0.34287 (13) | 0.30168 (14) | 0.0268 (5) | |
N21B | 0.6030 (2) | 0.32707 (12) | 0.21814 (13) | 0.0369 (5) | |
H21B | 0.592 (3) | 0.3475 (14) | 0.1561 (14) | 0.044* | |
H22B | 0.654 (2) | 0.2850 (12) | 0.2212 (19) | 0.044* | |
N3B | 0.53619 (18) | 0.29800 (10) | 0.38623 (11) | 0.0274 (4) | |
C4B | 0.4530 (2) | 0.31394 (13) | 0.46825 (14) | 0.0274 (5) | |
N41B | 0.4619 (2) | 0.27026 (12) | 0.55232 (13) | 0.0347 (5) | |
H41B | 0.528 (2) | 0.2362 (13) | 0.5550 (19) | 0.042* | |
H42B | 0.407 (2) | 0.2794 (14) | 0.6047 (15) | 0.042* | |
C5B | 0.3581 (2) | 0.37523 (13) | 0.46640 (16) | 0.0348 (5) | |
H5B | 0.2969 | 0.3843 | 0.5236 | 0.042* | |
C6B | 0.3574 (2) | 0.42020 (14) | 0.38122 (16) | 0.0343 (5) | |
H6B | 0.2970 | 0.4630 | 0.3784 | 0.041* | |
C1X | 0.8443 (3) | 0.43271 (16) | 0.0345 (2) | 0.0518 (7) | |
H1X1 | 0.7975 | 0.4379 | 0.1025 | 0.078* | |
H1X2 | 0.8538 | 0.4839 | 0.0020 | 0.078* | |
H1X3 | 0.9341 | 0.4102 | 0.0436 | 0.078* | |
C2X | 0.7636 (3) | 0.38063 (16) | −0.03418 (19) | 0.0441 (6) | |
O21X | 0.66069 (18) | 0.34777 (12) | 0.00005 (12) | 0.0524 (5) | |
N3X | 0.8089 (2) | 0.37062 (14) | −0.13257 (16) | 0.0507 (6) | |
C31X | 0.7378 (3) | 0.3197 (2) | −0.2014 (2) | 0.0666 (9) | |
H31A | 0.6505 | 0.3051 | −0.1688 | 0.100* | |
H31B | 0.7920 | 0.2730 | −0.2150 | 0.100* | |
H31C | 0.7225 | 0.3465 | −0.2672 | 0.100* | |
C32X | 0.9255 (3) | 0.4111 (2) | −0.1775 (2) | 0.0743 (10) | |
H32A | 0.9644 | 0.4447 | −0.1247 | 0.111* | |
H32B | 0.8974 | 0.4426 | −0.2363 | 0.111* | |
H32C | 0.9934 | 0.3732 | −0.2016 | 0.111* | |
C1Y | 0.0189 (3) | 0.68053 (19) | 0.4631 (2) | 0.0680 (9) | |
H1YA | 0.0568 | 0.7267 | 0.4958 | 0.102* | 0.584 (7) |
H1YB | −0.0766 | 0.6751 | 0.4848 | 0.102* | 0.584 (7) |
H1YC | 0.0264 | 0.6859 | 0.3872 | 0.102* | 0.584 (7) |
H1YD | −0.0373 | 0.7254 | 0.4827 | 0.102* | 0.416 (7) |
H1YE | 0.1020 | 0.6984 | 0.4269 | 0.102* | 0.416 (7) |
H1YF | −0.0312 | 0.6466 | 0.4169 | 0.102* | 0.416 (7) |
O21Y | 0.1604 (3) | 0.56219 (17) | 0.43991 (17) | 0.1078 (11) | |
C31Y | 0.1779 (5) | 0.5293 (2) | 0.6325 (2) | 0.0852 (12) | |
H3YA | 0.2131 | 0.5389 | 0.7017 | 0.128* | 0.584 (7) |
H3YB | 0.2534 | 0.5190 | 0.5831 | 0.128* | 0.584 (7) |
H3YC | 0.1174 | 0.4842 | 0.6354 | 0.128* | 0.584 (7) |
H3YD | 0.1390 | 0.5528 | 0.6961 | 0.128* | 0.416 (7) |
H3YE | 0.1476 | 0.4753 | 0.6276 | 0.128* | 0.416 (7) |
H3YF | 0.2769 | 0.5307 | 0.6344 | 0.128* | 0.416 (7) |
C32Y | 0.0213 (4) | 0.6485 (2) | 0.6695 (2) | 0.0854 (11) | |
H4YA | −0.0320 | 0.6169 | 0.7191 | 0.128* | 0.584 (7) |
H4YB | −0.0396 | 0.6800 | 0.6282 | 0.128* | 0.584 (7) |
H4YC | 0.0817 | 0.6827 | 0.7076 | 0.128* | 0.584 (7) |
H4YD | −0.0350 | 0.6950 | 0.6790 | 0.128* | 0.416 (7) |
H4YE | −0.0279 | 0.6032 | 0.6967 | 0.128* | 0.416 (7) |
H4YF | 0.1053 | 0.6550 | 0.7071 | 0.128* | 0.416 (7) |
C2Y | 0.0980 (6) | 0.6078 (3) | 0.4969 (4) | 0.0554 (15) | 0.584 (7) |
N3Y | 0.1039 (4) | 0.5967 (2) | 0.5988 (3) | 0.0509 (13) | 0.584 (7) |
C2Y' | 0.1306 (10) | 0.5754 (5) | 0.5361 (5) | 0.075 (3) | 0.416 (7) |
N3Y' | 0.0540 (6) | 0.6373 (3) | 0.5573 (4) | 0.0506 (18) | 0.416 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0320 (10) | 0.0302 (11) | 0.0184 (8) | 0.0025 (8) | 0.0013 (7) | −0.0010 (7) |
C2A | 0.0285 (11) | 0.0310 (13) | 0.0192 (9) | −0.0024 (9) | 0.0035 (8) | −0.0020 (8) |
S21A | 0.0414 (3) | 0.0478 (4) | 0.0179 (2) | 0.0139 (3) | 0.0071 (2) | 0.0008 (2) |
N3A | 0.0299 (10) | 0.0341 (12) | 0.0197 (8) | 0.0070 (8) | 0.0067 (7) | 0.0012 (7) |
C4A | 0.0314 (12) | 0.0352 (13) | 0.0207 (9) | −0.0024 (10) | 0.0049 (8) | −0.0006 (9) |
O41A | 0.0440 (10) | 0.0493 (11) | 0.0209 (7) | 0.0139 (8) | 0.0099 (6) | 0.0074 (7) |
C5A | 0.0351 (12) | 0.0377 (14) | 0.0181 (9) | 0.0033 (10) | 0.0063 (8) | −0.0045 (9) |
C6A | 0.0315 (12) | 0.0291 (13) | 0.0228 (9) | −0.0018 (10) | 0.0006 (8) | −0.0061 (8) |
O61A | 0.0461 (10) | 0.0356 (9) | 0.0218 (7) | 0.0131 (8) | 0.0024 (6) | −0.0050 (6) |
N1B | 0.0395 (11) | 0.0301 (11) | 0.0218 (8) | 0.0011 (8) | 0.0028 (7) | 0.0069 (7) |
C2B | 0.0311 (11) | 0.0272 (12) | 0.0220 (9) | −0.0045 (10) | 0.0022 (8) | 0.0023 (8) |
N21B | 0.0469 (12) | 0.0412 (13) | 0.0218 (8) | 0.0099 (9) | 0.0104 (8) | 0.0093 (8) |
N3B | 0.0316 (10) | 0.0313 (11) | 0.0188 (8) | −0.0002 (8) | 0.0052 (7) | 0.0016 (7) |
C4B | 0.0303 (12) | 0.0306 (12) | 0.0210 (9) | −0.0030 (9) | 0.0038 (8) | 0.0004 (8) |
N41B | 0.0420 (12) | 0.0387 (12) | 0.0225 (8) | 0.0094 (9) | 0.0121 (8) | 0.0068 (8) |
C5B | 0.0378 (13) | 0.0399 (14) | 0.0263 (10) | 0.0065 (10) | 0.0085 (9) | 0.0009 (9) |
C6B | 0.0361 (13) | 0.0363 (14) | 0.0303 (11) | 0.0056 (10) | 0.0035 (9) | 0.0015 (9) |
C1X | 0.0526 (17) | 0.0500 (18) | 0.0520 (15) | 0.0091 (13) | 0.0109 (12) | 0.0029 (13) |
C2X | 0.0447 (15) | 0.0496 (17) | 0.0374 (12) | 0.0151 (13) | 0.0074 (11) | 0.0160 (11) |
O21X | 0.0443 (11) | 0.0753 (14) | 0.0368 (9) | −0.0009 (10) | 0.0107 (7) | 0.0167 (9) |
N3X | 0.0467 (13) | 0.0657 (17) | 0.0387 (11) | 0.0089 (11) | 0.0132 (9) | 0.0112 (10) |
C31X | 0.0523 (18) | 0.105 (3) | 0.0426 (14) | 0.0062 (17) | 0.0019 (13) | −0.0005 (16) |
C32X | 0.059 (2) | 0.100 (3) | 0.0617 (18) | 0.0045 (18) | 0.0297 (15) | 0.0226 (18) |
C1Y | 0.070 (2) | 0.064 (2) | 0.0691 (19) | 0.0144 (16) | 0.0058 (16) | 0.0181 (16) |
O21Y | 0.158 (3) | 0.115 (2) | 0.0500 (12) | 0.085 (2) | 0.0147 (14) | −0.0126 (13) |
C31Y | 0.136 (4) | 0.062 (2) | 0.0581 (18) | 0.038 (2) | −0.014 (2) | −0.0018 (16) |
C32Y | 0.090 (3) | 0.103 (3) | 0.0623 (19) | 0.001 (2) | 0.0225 (17) | −0.0313 (19) |
C2Y | 0.067 (4) | 0.051 (4) | 0.047 (3) | 0.018 (3) | 0.013 (3) | −0.003 (2) |
N3Y | 0.065 (3) | 0.047 (3) | 0.040 (2) | 0.011 (2) | 0.0033 (19) | −0.0061 (19) |
C2Y' | 0.107 (7) | 0.065 (6) | 0.054 (5) | 0.045 (5) | −0.010 (5) | −0.012 (4) |
N3Y' | 0.059 (4) | 0.046 (4) | 0.046 (3) | 0.014 (3) | 0.012 (3) | −0.004 (3) |
N1A—C2A | 1.339 (3) | C31X—H31A | 0.9800 |
N1A—C6A | 1.390 (3) | C31X—H31B | 0.9800 |
N1A—H1A | 0.846 (15) | C31X—H31C | 0.9800 |
C2A—N3A | 1.350 (3) | C32X—H32A | 0.9800 |
C2A—S21A | 1.682 (2) | C32X—H32B | 0.9800 |
N3A—C4A | 1.400 (2) | C32X—H32C | 0.9800 |
N3A—H3A | 0.874 (16) | C1Y—N3Y' | 1.474 (5) |
C4A—O41A | 1.258 (2) | C1Y—C2Y | 1.547 (5) |
C4A—C5A | 1.389 (3) | C1Y—H1YA | 0.9800 |
C5A—C6A | 1.387 (3) | C1Y—H1YB | 0.9800 |
C5A—H5A | 0.9500 | C1Y—H1YC | 0.9800 |
C6A—O61A | 1.262 (3) | C1Y—H1YD | 0.9800 |
N1B—C2B | 1.352 (3) | C1Y—H1YE | 0.9800 |
N1B—C6B | 1.354 (3) | C1Y—H1YF | 0.9800 |
N1B—H1B | 0.865 (16) | O21Y—C2Y | 1.227 (5) |
C2B—N21B | 1.321 (3) | O21Y—C2Y' | 1.283 (6) |
C2B—N3B | 1.340 (2) | C31Y—N3Y | 1.448 (5) |
N21B—H21B | 0.881 (16) | C31Y—C2Y' | 1.556 (6) |
N21B—H22B | 0.885 (17) | C31Y—H3YA | 0.9800 |
N3B—C4B | 1.345 (3) | C31Y—H3YB | 0.9800 |
C4B—N41B | 1.323 (3) | C31Y—H3YC | 0.9800 |
C4B—C5B | 1.414 (3) | C31Y—H3YD | 0.9800 |
N41B—H41B | 0.878 (16) | C31Y—H3YE | 0.9800 |
N41B—H42B | 0.866 (17) | C31Y—H3YF | 0.9800 |
C5B—C6B | 1.342 (3) | C32Y—N3Y' | 1.480 (5) |
C5B—H5B | 0.9500 | C32Y—N3Y | 1.498 (5) |
C6B—H6B | 0.9500 | C32Y—H4YA | 0.9800 |
C1X—C2X | 1.506 (4) | C32Y—H4YB | 0.9800 |
C1X—H1X1 | 0.9800 | C32Y—H4YC | 0.9800 |
C1X—H1X2 | 0.9800 | C32Y—H4YD | 0.9800 |
C1X—H1X3 | 0.9800 | C32Y—H4YE | 0.9800 |
C2X—O21X | 1.233 (3) | C32Y—H4YF | 0.9800 |
C2X—N3X | 1.340 (3) | C2Y—N3Y | 1.327 (6) |
N3X—C31X | 1.446 (4) | C2Y'—N3Y' | 1.332 (7) |
N3X—C32X | 1.450 (4) | ||
C2A—N1A—C6A | 125.17 (17) | H31A—C31X—H31C | 109.5 |
C2A—N1A—H1A | 119.7 (16) | H31B—C31X—H31C | 109.5 |
C6A—N1A—H1A | 115.1 (16) | N3X—C32X—H32A | 109.5 |
N1A—C2A—N3A | 115.85 (17) | N3X—C32X—H32B | 109.5 |
N1A—C2A—S21A | 121.13 (15) | H32A—C32X—H32B | 109.5 |
N3A—C2A—S21A | 123.01 (16) | N3X—C32X—H32C | 109.5 |
C2A—N3A—C4A | 124.60 (18) | H32A—C32X—H32C | 109.5 |
C2A—N3A—H3A | 118.5 (15) | H32B—C32X—H32C | 109.5 |
C4A—N3A—H3A | 116.8 (15) | C2Y—C1Y—H1YA | 109.5 |
O41A—C4A—C5A | 126.01 (18) | C2Y—C1Y—H1YB | 109.5 |
O41A—C4A—N3A | 117.38 (19) | H1YA—C1Y—H1YB | 109.5 |
C5A—C4A—N3A | 116.61 (17) | C2Y—C1Y—H1YC | 109.5 |
C6A—C5A—C4A | 120.92 (18) | H1YA—C1Y—H1YC | 109.5 |
C6A—C5A—H5A | 119.5 | H1YB—C1Y—H1YC | 109.5 |
C4A—C5A—H5A | 119.5 | N3Y'—C1Y—H1YD | 109.5 |
O61A—C6A—C5A | 126.44 (19) | N3Y'—C1Y—H1YE | 109.5 |
O61A—C6A—N1A | 116.72 (18) | H1YD—C1Y—H1YE | 109.5 |
C5A—C6A—N1A | 116.83 (19) | N3Y'—C1Y—H1YF | 109.5 |
C2B—N1B—C6B | 120.42 (18) | H1YD—C1Y—H1YF | 109.5 |
C2B—N1B—H1B | 122.4 (16) | H1YE—C1Y—H1YF | 109.5 |
C6B—N1B—H1B | 117.2 (16) | N3Y—C31Y—H3YA | 109.5 |
N21B—C2B—N3B | 119.2 (2) | N3Y—C31Y—H3YB | 109.5 |
N21B—C2B—N1B | 118.67 (18) | H3YA—C31Y—H3YB | 109.5 |
N3B—C2B—N1B | 122.14 (18) | N3Y—C31Y—H3YC | 109.5 |
C2B—N21B—H21B | 124.9 (17) | H3YA—C31Y—H3YC | 109.5 |
C2B—N21B—H22B | 116.4 (17) | H3YB—C31Y—H3YC | 109.5 |
H21B—N21B—H22B | 117 (2) | C2Y'—C31Y—H3YD | 109.5 |
C2B—N3B—C4B | 117.48 (18) | C2Y'—C31Y—H3YE | 109.5 |
N41B—C4B—N3B | 118.0 (2) | H3YD—C31Y—H3YE | 109.5 |
N41B—C4B—C5B | 120.04 (19) | C2Y'—C31Y—H3YF | 109.5 |
N3B—C4B—C5B | 121.93 (18) | H3YD—C31Y—H3YF | 109.5 |
C4B—N41B—H41B | 118.8 (17) | H3YE—C31Y—H3YF | 109.5 |
C4B—N41B—H42B | 118.4 (17) | N3Y—C32Y—H4YA | 109.5 |
H41B—N41B—H42B | 123 (2) | N3Y—C32Y—H4YB | 109.5 |
C6B—C5B—C4B | 117.8 (2) | H4YA—C32Y—H4YB | 109.5 |
C6B—C5B—H5B | 121.1 | N3Y—C32Y—H4YC | 109.5 |
C4B—C5B—H5B | 121.1 | H4YA—C32Y—H4YC | 109.5 |
C5B—C6B—N1B | 120.0 (2) | H4YB—C32Y—H4YC | 109.5 |
C5B—C6B—H6B | 120.0 | N3Y'—C32Y—H4YD | 109.5 |
N1B—C6B—H6B | 120.0 | N3Y'—C32Y—H4YE | 109.5 |
C2X—C1X—H1X1 | 109.5 | H4YD—C32Y—H4YE | 109.5 |
C2X—C1X—H1X2 | 109.5 | N3Y'—C32Y—H4YF | 109.5 |
H1X1—C1X—H1X2 | 109.5 | H4YD—C32Y—H4YF | 109.5 |
C2X—C1X—H1X3 | 109.5 | H4YE—C32Y—H4YF | 109.5 |
H1X1—C1X—H1X3 | 109.5 | O21Y—C2Y—N3Y | 117.4 (4) |
H1X2—C1X—H1X3 | 109.5 | O21Y—C2Y—C1Y | 126.9 (4) |
O21X—C2X—N3X | 121.7 (3) | N3Y—C2Y—C1Y | 115.6 (4) |
O21X—C2X—C1X | 120.8 (2) | C2Y—N3Y—C31Y | 116.7 (4) |
N3X—C2X—C1X | 117.6 (2) | C2Y—N3Y—C32Y | 118.2 (4) |
C2X—N3X—C31X | 120.1 (2) | C31Y—N3Y—C32Y | 124.6 (3) |
C2X—N3X—C32X | 123.4 (3) | O21Y—C2Y'—N3Y' | 116.8 (5) |
C31X—N3X—C32X | 116.4 (2) | O21Y—C2Y'—C31Y | 127.7 (5) |
N3X—C31X—H31A | 109.5 | N3Y'—C2Y'—C31Y | 115.4 (5) |
N3X—C31X—H31B | 109.5 | C2Y'—N3Y'—C1Y | 112.6 (5) |
H31A—C31X—H31B | 109.5 | C2Y'—N3Y'—C32Y | 114.2 (5) |
N3X—C31X—H31C | 109.5 | C1Y—N3Y'—C32Y | 133.3 (4) |
C6A—N1A—C2A—N3A | −0.7 (3) | C2B—N3B—C4B—C5B | 0.3 (3) |
C6A—N1A—C2A—S21A | 178.18 (16) | N41B—C4B—C5B—C6B | 176.9 (2) |
N1A—C2A—N3A—C4A | 0.9 (3) | N3B—C4B—C5B—C6B | −3.1 (3) |
S21A—C2A—N3A—C4A | −177.98 (16) | C4B—C5B—C6B—N1B | 2.2 (3) |
C2A—N3A—C4A—O41A | −179.6 (2) | C2B—N1B—C6B—C5B | 1.5 (3) |
C2A—N3A—C4A—C5A | 0.1 (3) | O21X—C2X—N3X—C31X | −0.6 (4) |
O41A—C4A—C5A—C6A | 178.4 (2) | C1X—C2X—N3X—C31X | 178.4 (2) |
N3A—C4A—C5A—C6A | −1.4 (3) | O21X—C2X—N3X—C32X | 176.8 (3) |
C4A—C5A—C6A—O61A | −179.7 (2) | C1X—C2X—N3X—C32X | −4.2 (4) |
C4A—C5A—C6A—N1A | 1.5 (3) | O21Y—C2Y—N3Y—C31Y | −3.2 (8) |
C2A—N1A—C6A—O61A | −179.40 (19) | C1Y—C2Y—N3Y—C31Y | −179.7 (4) |
C2A—N1A—C6A—C5A | −0.5 (3) | O21Y—C2Y—N3Y—C32Y | −176.2 (5) |
C6B—N1B—C2B—N21B | 176.3 (2) | C1Y—C2Y—N3Y—C32Y | 7.3 (7) |
C6B—N1B—C2B—N3B | −4.5 (3) | O21Y—C2Y'—N3Y'—C1Y | −0.8 (11) |
N21B—C2B—N3B—C4B | −177.37 (19) | C31Y—C2Y'—N3Y'—C1Y | 176.9 (6) |
N1B—C2B—N3B—C4B | 3.5 (3) | O21Y—C2Y'—N3Y'—C32Y | 179.0 (7) |
C2B—N3B—C4B—N41B | −179.71 (19) | C31Y—C2Y'—N3Y'—C32Y | −3.2 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O61Ai | 0.85 (2) | 1.91 (2) | 2.753 (2) | 175 (2) |
N3A—H3A···N3B | 0.87 (2) | 2.23 (2) | 3.099 (3) | 173 (2) |
N1B—H1B···O61Aii | 0.87 (2) | 1.85 (2) | 2.700 (2) | 168 (2) |
N21B—H21B···O21X | 0.88 (2) | 2.10 (2) | 2.866 (2) | 145 (2) |
N21B—H22B···O41A | 0.89 (2) | 1.91 (2) | 2.795 (3) | 174 (2) |
N41B—H41B···S21A | 0.88 (2) | 2.47 (2) | 3.336 (2) | 171 (2) |
N41B—H42B···O41Aiii | 0.87 (2) | 1.98 (2) | 2.846 (2) | 173 (2) |
C6B—H6B···O21Y | 0.95 | 2.30 | 3.203 (3) | 158 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z+1/2. |
TU is 2-thiouracil, BA is barbituric acid, TBA is 2-thiobarbituric acid, DMAC is N,N-dimethylacetamide, NMP is 1-methylpyrrolidin-2-one, DMSO is dimethyl sulfoxide and DMF is N,N-dimethylformamide. |
Crystal | Compound 1 (mg, mmol) | DAPY (mg, mmol) | Solvent (µl) | Temperature (K) |
(I) | TU, 2.4, 0.019 | 2.0, 0.018 | DMAC (125) | 323 |
(II) | - | 3.1, 0.028 | Dioxane (125) | 295 |
(III) | - | 5.5, 0.050 | DMAC (150) | 295 |
(IV) | - | 4.9, 0.044 | NMP (50) | 295 |
(V) | BA, 1.9, 0.015 | 4.0, 0.036 | DMSO(44) | 323 |
(VI) | TBA, 2.2, 0.015 | 1.4, 0.013 | DMF (70) | 277 |
(VII) | TBA, 4.3, 0.030 | 1.7, 0.015 | DMAC (105) | 323 |