Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017181/eg3230sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017181/eg3230Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017181/eg3230IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017181/eg3230IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017181/eg3230IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017181/eg3230Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017181/eg3230VIsup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617017181/eg3230sup8.pdf |
CCDC references: 1588311; 1588310; 1588309; 1588308; 1588307; 1588306
For all structures, 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: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Version 3.9, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C5H6N2OS·2C4H6N4 | Z = 2 |
Mr = 362.43 | F(000) = 380 |
Triclinic, P1 | Dx = 1.426 Mg m−3 |
a = 7.7255 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1381 (14) Å | Cell parameters from 11686 reflections |
c = 12.4594 (17) Å | θ = 3.4–26.2° |
α = 92.241 (11)° | µ = 0.22 mm−1 |
β = 104.034 (10)° | T = 173 K |
γ = 97.248 (11)° | Block, colourless |
V = 844.3 (2) Å3 | 0.31 × 0.21 × 0.20 mm |
STOE IPDS II two-circle diffractometer | 2752 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.041 |
ω scans | θmax = 25.9°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→8 |
Tmin = 0.821, Tmax = 1.000 | k = −11→11 |
7146 measured reflections | l = −15→15 |
3233 independent reflections |
Refinement on F2 | 10 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.1481P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3233 reflections | Δρmax = 0.23 e Å−3 |
257 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 | 0.36696 (18) | 0.55829 (15) | 0.66190 (11) | 0.0263 (3) | |
H1A | 0.434 (2) | 0.556 (2) | 0.7282 (13) | 0.032* | |
C2A | 0.3463 (2) | 0.43970 (17) | 0.59002 (12) | 0.0246 (3) | |
S21A | 0.44038 (6) | 0.28702 (5) | 0.62632 (3) | 0.03083 (13) | |
N3A | 0.24595 (17) | 0.45105 (14) | 0.48589 (10) | 0.0239 (3) | |
H3A | 0.228 (2) | 0.3744 (18) | 0.4370 (14) | 0.029* | |
C4A | 0.1669 (2) | 0.57323 (17) | 0.44852 (12) | 0.0243 (3) | |
O41A | 0.07836 (16) | 0.56900 (12) | 0.35151 (9) | 0.0305 (3) | |
C5A | 0.1940 (2) | 0.69727 (17) | 0.52912 (12) | 0.0246 (3) | |
C51A | 0.1126 (3) | 0.83359 (18) | 0.49507 (14) | 0.0333 (4) | |
H51A | 0.1522 | 0.9104 | 0.5564 | 0.050* | |
H52A | −0.0191 | 0.8107 | 0.4763 | 0.050* | |
H53A | 0.1514 | 0.8690 | 0.4302 | 0.050* | |
C6A | 0.2927 (2) | 0.68306 (18) | 0.63184 (13) | 0.0268 (3) | |
H6A | 0.3117 | 0.7634 | 0.6860 | 0.032* | |
N1B | 0.57109 (17) | 0.59745 (15) | 0.88240 (11) | 0.0273 (3) | |
C2B | 0.7191 (2) | 0.54425 (17) | 0.93589 (12) | 0.0235 (3) | |
N21B | 0.7726 (2) | 0.43075 (15) | 0.88358 (12) | 0.0291 (3) | |
H21B | 0.720 (3) | 0.413 (2) | 0.8126 (13) | 0.035* | |
H22B | 0.888 (2) | 0.424 (2) | 0.9046 (15) | 0.035* | |
N3B | 0.81924 (17) | 0.58941 (14) | 1.03905 (10) | 0.0242 (3) | |
C4B | 0.7641 (2) | 0.69717 (18) | 1.09314 (12) | 0.0256 (3) | |
N41B | 0.8598 (2) | 0.74284 (18) | 1.19726 (11) | 0.0336 (3) | |
H41B | 0.938 (3) | 0.688 (2) | 1.2337 (16) | 0.040* | |
H42B | 0.805 (3) | 0.791 (2) | 1.2392 (16) | 0.040* | |
C5B | 0.6133 (2) | 0.76298 (18) | 1.04278 (13) | 0.0290 (3) | |
H5B | 0.5764 | 0.8421 | 1.0795 | 0.035* | |
C6B | 0.5225 (2) | 0.70760 (18) | 0.93867 (13) | 0.0289 (3) | |
H6B | 0.4185 | 0.7492 | 0.9035 | 0.035* | |
N1C | 0.19948 (19) | 0.21725 (15) | 0.32059 (11) | 0.0280 (3) | |
C2C | 0.0924 (2) | 0.20734 (16) | 0.21725 (12) | 0.0246 (3) | |
N21C | −0.02932 (19) | 0.30457 (16) | 0.19594 (12) | 0.0296 (3) | |
H21C | −0.008 (3) | 0.3812 (19) | 0.2444 (15) | 0.035* | |
H22C | −0.073 (3) | 0.319 (2) | 0.1239 (13) | 0.035* | |
N3C | 0.08906 (18) | 0.10809 (14) | 0.13442 (10) | 0.0261 (3) | |
C4C | 0.2033 (2) | 0.00810 (17) | 0.15581 (13) | 0.0272 (3) | |
N41C | 0.2012 (2) | −0.09037 (16) | 0.07231 (13) | 0.0341 (3) | |
H41C | 0.114 (3) | −0.090 (2) | 0.0102 (14) | 0.041* | |
H42C | 0.254 (3) | −0.169 (2) | 0.0863 (17) | 0.041* | |
C5C | 0.3224 (2) | 0.01019 (18) | 0.26110 (14) | 0.0322 (4) | |
H5C | 0.4058 | −0.0588 | 0.2771 | 0.039* | |
C6C | 0.3129 (2) | 0.11562 (18) | 0.33922 (13) | 0.0311 (4) | |
H6C | 0.3912 | 0.1174 | 0.4111 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0243 (7) | 0.0308 (7) | 0.0209 (6) | 0.0058 (5) | −0.0007 (5) | 0.0002 (5) |
C2A | 0.0195 (7) | 0.0304 (8) | 0.0240 (7) | 0.0043 (6) | 0.0052 (6) | 0.0037 (6) |
S21A | 0.0323 (2) | 0.0341 (2) | 0.0269 (2) | 0.01514 (16) | 0.00322 (16) | 0.00457 (15) |
N3A | 0.0245 (7) | 0.0245 (7) | 0.0210 (6) | 0.0059 (5) | 0.0015 (5) | −0.0003 (5) |
C4A | 0.0222 (8) | 0.0258 (8) | 0.0243 (7) | 0.0035 (6) | 0.0046 (6) | 0.0028 (6) |
O41A | 0.0349 (6) | 0.0288 (6) | 0.0235 (6) | 0.0089 (5) | −0.0029 (5) | 0.0017 (4) |
C5A | 0.0237 (8) | 0.0238 (7) | 0.0264 (7) | 0.0030 (6) | 0.0065 (6) | 0.0011 (6) |
C51A | 0.0400 (10) | 0.0253 (8) | 0.0331 (8) | 0.0078 (7) | 0.0046 (7) | 0.0016 (6) |
C6A | 0.0247 (8) | 0.0275 (8) | 0.0269 (8) | 0.0015 (6) | 0.0056 (6) | −0.0024 (6) |
N1B | 0.0221 (7) | 0.0323 (7) | 0.0260 (6) | 0.0066 (5) | 0.0015 (5) | 0.0032 (5) |
C2B | 0.0196 (7) | 0.0259 (7) | 0.0250 (7) | 0.0032 (6) | 0.0050 (6) | 0.0062 (6) |
N21B | 0.0253 (7) | 0.0324 (7) | 0.0277 (7) | 0.0077 (6) | 0.0017 (6) | −0.0023 (5) |
N3B | 0.0221 (6) | 0.0282 (7) | 0.0228 (6) | 0.0064 (5) | 0.0046 (5) | 0.0042 (5) |
C4B | 0.0238 (8) | 0.0315 (8) | 0.0222 (7) | 0.0050 (6) | 0.0061 (6) | 0.0047 (6) |
N41B | 0.0352 (8) | 0.0439 (9) | 0.0225 (7) | 0.0179 (7) | 0.0029 (6) | 0.0002 (6) |
C5B | 0.0291 (8) | 0.0330 (9) | 0.0277 (8) | 0.0121 (7) | 0.0081 (6) | 0.0030 (6) |
C6B | 0.0231 (8) | 0.0350 (9) | 0.0288 (8) | 0.0106 (6) | 0.0028 (6) | 0.0071 (6) |
N1C | 0.0311 (7) | 0.0263 (7) | 0.0258 (6) | 0.0046 (5) | 0.0057 (5) | 0.0006 (5) |
C2C | 0.0251 (8) | 0.0225 (7) | 0.0260 (7) | 0.0004 (6) | 0.0078 (6) | 0.0013 (6) |
N21C | 0.0325 (8) | 0.0287 (7) | 0.0265 (7) | 0.0093 (6) | 0.0039 (6) | −0.0033 (5) |
N3C | 0.0282 (7) | 0.0232 (6) | 0.0258 (6) | 0.0040 (5) | 0.0050 (5) | 0.0003 (5) |
C4C | 0.0289 (8) | 0.0227 (7) | 0.0306 (8) | 0.0025 (6) | 0.0094 (6) | 0.0003 (6) |
N41C | 0.0387 (8) | 0.0280 (7) | 0.0343 (8) | 0.0124 (6) | 0.0037 (6) | −0.0036 (6) |
C5C | 0.0336 (9) | 0.0276 (8) | 0.0349 (9) | 0.0099 (7) | 0.0046 (7) | 0.0038 (6) |
C6C | 0.0329 (9) | 0.0306 (8) | 0.0283 (8) | 0.0049 (7) | 0.0040 (7) | 0.0039 (6) |
N1A—C2A | 1.347 (2) | C4B—N41B | 1.349 (2) |
N1A—C6A | 1.365 (2) | C4B—C5B | 1.401 (2) |
N1A—H1A | 0.865 (15) | N41B—H41B | 0.886 (16) |
C2A—N3A | 1.356 (2) | N41B—H42B | 0.881 (15) |
C2A—S21A | 1.6806 (16) | C5B—C6B | 1.360 (2) |
N3A—C4A | 1.383 (2) | C5B—H5B | 0.9500 |
N3A—H3A | 0.885 (14) | C6B—H6B | 0.9500 |
C4A—O41A | 1.2324 (18) | N1C—C2C | 1.344 (2) |
C4A—C5A | 1.444 (2) | N1C—C6C | 1.345 (2) |
C5A—C6A | 1.342 (2) | C2C—N3C | 1.3404 (19) |
C5A—C51A | 1.495 (2) | C2C—N21C | 1.361 (2) |
C51A—H51A | 0.9800 | N21C—H21C | 0.879 (15) |
C51A—H52A | 0.9800 | N21C—H22C | 0.900 (15) |
C51A—H53A | 0.9800 | N3C—C4C | 1.339 (2) |
C6A—H6A | 0.9500 | C4C—N41C | 1.344 (2) |
N1B—C2B | 1.336 (2) | C4C—C5C | 1.406 (2) |
N1B—C6B | 1.346 (2) | N41C—H41C | 0.893 (16) |
C2B—N3B | 1.348 (2) | N41C—H42C | 0.874 (16) |
C2B—N21B | 1.363 (2) | C5C—C6C | 1.364 (2) |
N21B—H21B | 0.878 (15) | C5C—H5C | 0.9500 |
N21B—H22B | 0.877 (15) | C6C—H6C | 0.9500 |
N3B—C4B | 1.341 (2) | ||
C2A—N1A—C6A | 122.19 (13) | N3B—C4B—N41B | 118.13 (15) |
C2A—N1A—H1A | 118.3 (13) | N3B—C4B—C5B | 121.31 (14) |
C6A—N1A—H1A | 119.4 (13) | N41B—C4B—C5B | 120.55 (15) |
N1A—C2A—N3A | 115.96 (14) | C4B—N41B—H41B | 119.5 (13) |
N1A—C2A—S21A | 122.26 (12) | C4B—N41B—H42B | 117.0 (14) |
N3A—C2A—S21A | 121.78 (12) | H41B—N41B—H42B | 114.6 (19) |
C2A—N3A—C4A | 125.54 (13) | C6B—C5B—C4B | 116.50 (15) |
C2A—N3A—H3A | 118.2 (12) | C6B—C5B—H5B | 121.8 |
C4A—N3A—H3A | 116.3 (12) | C4B—C5B—H5B | 121.8 |
O41A—C4A—N3A | 119.02 (14) | N1B—C6B—C5B | 124.04 (15) |
O41A—C4A—C5A | 124.93 (15) | N1B—C6B—H6B | 118.0 |
N3A—C4A—C5A | 116.05 (13) | C5B—C6B—H6B | 118.0 |
C6A—C5A—C4A | 117.33 (15) | C2C—N1C—C6C | 114.62 (14) |
C6A—C5A—C51A | 123.41 (14) | N3C—C2C—N1C | 126.55 (15) |
C4A—C5A—C51A | 119.26 (14) | N3C—C2C—N21C | 116.82 (14) |
C5A—C51A—H51A | 109.5 | N1C—C2C—N21C | 116.58 (14) |
C5A—C51A—H52A | 109.5 | C2C—N21C—H21C | 115.0 (14) |
H51A—C51A—H52A | 109.5 | C2C—N21C—H22C | 115.5 (13) |
C5A—C51A—H53A | 109.5 | H21C—N21C—H22C | 118.1 (18) |
H51A—C51A—H53A | 109.5 | C4C—N3C—C2C | 117.34 (13) |
H52A—C51A—H53A | 109.5 | N3C—C4C—N41C | 117.28 (15) |
C5A—C6A—N1A | 122.92 (14) | N3C—C4C—C5C | 120.47 (14) |
C5A—C6A—H6A | 118.5 | N41C—C4C—C5C | 122.23 (16) |
N1A—C6A—H6A | 118.5 | C4C—N41C—H41C | 116.8 (14) |
C2B—N1B—C6B | 115.20 (13) | C4C—N41C—H42C | 119.9 (14) |
N1B—C2B—N3B | 126.10 (14) | H41C—N41C—H42C | 120 (2) |
N1B—C2B—N21B | 117.70 (14) | C6C—C5C—C4C | 117.06 (16) |
N3B—C2B—N21B | 116.17 (14) | C6C—C5C—H5C | 121.5 |
C2B—N21B—H21B | 115.7 (13) | C4C—C5C—H5C | 121.5 |
C2B—N21B—H22B | 115.2 (13) | N1C—C6C—C5C | 123.96 (15) |
H21B—N21B—H22B | 117.1 (18) | N1C—C6C—H6C | 118.0 |
C4B—N3B—C2B | 116.80 (13) | C5C—C6C—H6C | 118.0 |
C6A—N1A—C2A—N3A | −0.5 (2) | C2B—N3B—C4B—N41B | 178.86 (14) |
C6A—N1A—C2A—S21A | 179.01 (12) | C2B—N3B—C4B—C5B | −2.3 (2) |
N1A—C2A—N3A—C4A | 0.8 (2) | N3B—C4B—C5B—C6B | 2.7 (2) |
S21A—C2A—N3A—C4A | −178.68 (12) | N41B—C4B—C5B—C6B | −178.53 (15) |
C2A—N3A—C4A—O41A | −179.86 (14) | C2B—N1B—C6B—C5B | −0.4 (2) |
C2A—N3A—C4A—C5A | −0.7 (2) | C4B—C5B—C6B—N1B | −1.2 (2) |
O41A—C4A—C5A—C6A | 179.29 (15) | C6C—N1C—C2C—N3C | 0.1 (2) |
N3A—C4A—C5A—C6A | 0.1 (2) | C6C—N1C—C2C—N21C | 177.61 (14) |
O41A—C4A—C5A—C51A | −0.8 (2) | N1C—C2C—N3C—C4C | 0.1 (2) |
N3A—C4A—C5A—C51A | −179.99 (14) | N21C—C2C—N3C—C4C | −177.40 (14) |
C4A—C5A—C6A—N1A | 0.2 (2) | C2C—N3C—C4C—N41C | −179.29 (14) |
C51A—C5A—C6A—N1A | −179.72 (15) | C2C—N3C—C4C—C5C | −0.8 (2) |
C2A—N1A—C6A—C5A | 0.0 (2) | N3C—C4C—C5C—C6C | 1.2 (2) |
C6B—N1B—C2B—N3B | 0.9 (2) | N41C—C4C—C5C—C6C | 179.68 (16) |
C6B—N1B—C2B—N21B | 178.84 (14) | C2C—N1C—C6C—C5C | 0.4 (2) |
N1B—C2B—N3B—C4B | 0.5 (2) | C4C—C5C—C6C—N1C | −1.0 (3) |
N21B—C2B—N3B—C4B | −177.51 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···N1B | 0.87 (2) | 1.95 (2) | 2.8003 (19) | 167 (2) |
N3A—H3A···N1C | 0.89 (1) | 1.95 (2) | 2.8352 (19) | 175 (2) |
N21B—H21B···S21A | 0.88 (2) | 2.85 (2) | 3.6629 (16) | 155 (2) |
N21B—H22B···N3Bi | 0.88 (2) | 2.22 (2) | 3.097 (2) | 179 (2) |
N41B—H41B···O41Aii | 0.89 (2) | 2.04 (2) | 2.8998 (19) | 163 (2) |
N41B—H42B···S21Aiii | 0.88 (2) | 2.87 (2) | 3.5560 (16) | 136 (2) |
N21C—H21C···O41A | 0.88 (2) | 2.07 (2) | 2.9381 (18) | 171 (2) |
N41C—H41C···N3Civ | 0.89 (2) | 2.07 (2) | 2.960 (2) | 176 (2) |
N41C—H42C···N21Bv | 0.87 (2) | 2.43 (2) | 3.202 (2) | 148 (2) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x+1, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y, −z; (v) −x+1, −y, −z+1. |
2C5H6N2OS·C3H7NO·2C4H6N4 | F(000) = 1216 |
Mr = 577.71 | Dx = 1.444 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0743 (10) Å | Cell parameters from 21482 reflections |
b = 14.383 (1) Å | θ = 3.3–26.2° |
c = 18.647 (2) Å | µ = 0.25 mm−1 |
β = 100.427 (8)° | T = 173 K |
V = 2657.3 (4) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.26 × 0.11 mm |
STOE IPDS II two-circle diffractometer | 4157 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.047 |
ω scans | θmax = 25.9°, θmin = 3.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −12→12 |
Tmin = 0.688, Tmax = 1.000 | k = −17→17 |
11389 measured reflections | l = −21→22 |
4664 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0551P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.091 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.21 e Å−3 |
4664 reflections | Δρmin = −0.29 e Å−3 |
421 parameters | Absolute structure: Refined as an inversion twin. |
128 restraints | Absolute structure parameter: 0.24 (10) |
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 inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.3216 (3) | 0.1925 (2) | 0.64680 (17) | 0.0266 (7) | |
H1A | 0.237 (3) | 0.202 (3) | 0.625 (2) | 0.032* | |
C2A | 0.4209 (4) | 0.2179 (3) | 0.6122 (2) | 0.0256 (8) | |
S21A | 0.39325 (9) | 0.27994 (7) | 0.53405 (5) | 0.0296 (2) | |
N3A | 0.5471 (3) | 0.1914 (2) | 0.64471 (16) | 0.0244 (7) | |
H3A | 0.613 (3) | 0.210 (3) | 0.624 (2) | 0.029* | |
C4A | 0.5804 (4) | 0.1447 (3) | 0.7112 (2) | 0.0256 (9) | |
O41A | 0.6992 (3) | 0.1255 (2) | 0.73535 (14) | 0.0309 (6) | |
C5A | 0.4691 (4) | 0.1210 (3) | 0.74581 (19) | 0.0261 (8) | |
C51A | 0.4957 (4) | 0.0718 (3) | 0.8178 (2) | 0.0296 (9) | |
H51A | 0.4101 | 0.0609 | 0.8344 | 0.044* | |
H51B | 0.5546 | 0.1102 | 0.8537 | 0.044* | |
H51C | 0.5399 | 0.0121 | 0.8125 | 0.044* | |
C6A | 0.3438 (4) | 0.1454 (3) | 0.71190 (19) | 0.0261 (8) | |
H6A | 0.2688 | 0.1295 | 0.7338 | 0.031* | |
N1C | 1.0462 (3) | 0.2247 (2) | 0.58547 (17) | 0.0289 (7) | |
C2C | 0.9303 (4) | 0.2061 (3) | 0.6080 (2) | 0.0283 (9) | |
N21C | 0.9373 (4) | 0.1707 (3) | 0.6755 (2) | 0.0413 (10) | |
H21C | 1.006 (4) | 0.172 (3) | 0.711 (2) | 0.050* | |
H22C | 0.866 (4) | 0.164 (3) | 0.696 (3) | 0.050* | |
N3C | 0.8036 (3) | 0.2186 (2) | 0.56911 (16) | 0.0265 (7) | |
C4C | 0.7966 (4) | 0.2516 (3) | 0.5011 (2) | 0.0243 (8) | |
N41C | 0.6727 (4) | 0.2630 (3) | 0.46025 (19) | 0.0322 (8) | |
H41C | 0.607 (4) | 0.262 (3) | 0.486 (2) | 0.039* | |
H42C | 0.670 (5) | 0.295 (3) | 0.4200 (18) | 0.039* | |
C5C | 0.9122 (4) | 0.2726 (3) | 0.4723 (2) | 0.0303 (9) | |
H5C | 0.9066 | 0.2951 | 0.4240 | 0.036* | |
C6C | 1.0326 (4) | 0.2591 (3) | 0.5173 (2) | 0.0313 (9) | |
H6C | 1.1123 | 0.2749 | 0.4995 | 0.038* | |
N1B | 0.7482 (3) | 0.0814 (2) | 0.17434 (17) | 0.0276 (7) | |
H1B | 0.836 (3) | 0.095 (3) | 0.192 (2) | 0.033* | |
C2B | 0.6497 (4) | 0.1089 (3) | 0.2094 (2) | 0.0261 (8) | |
S21B | 0.68032 (9) | 0.16828 (7) | 0.28776 (5) | 0.0330 (3) | |
N3B | 0.5213 (3) | 0.0857 (2) | 0.17654 (17) | 0.0250 (7) | |
H3B | 0.453 (3) | 0.100 (3) | 0.200 (2) | 0.030* | |
C4B | 0.4874 (4) | 0.0408 (3) | 0.1099 (2) | 0.0268 (9) | |
O41B | 0.3677 (3) | 0.0234 (2) | 0.08515 (15) | 0.0376 (7) | |
C5B | 0.5966 (4) | 0.0146 (3) | 0.0741 (2) | 0.0270 (8) | |
C51B | 0.5645 (5) | −0.0333 (3) | 0.0021 (2) | 0.0336 (10) | |
H51D | 0.5162 | 0.0096 | −0.0344 | 0.050* | |
H51E | 0.5078 | −0.0877 | 0.0061 | 0.050* | |
H51F | 0.6485 | −0.0533 | −0.0129 | 0.050* | |
C6B | 0.7230 (4) | 0.0348 (3) | 0.1089 (2) | 0.0280 (9) | |
H6B | 0.7972 | 0.0162 | 0.0873 | 0.034* | |
N1D | 0.0259 (3) | 0.1176 (2) | 0.23786 (17) | 0.0312 (8) | |
C2D | 0.1417 (4) | 0.1009 (3) | 0.2147 (2) | 0.0294 (9) | |
N21D | 0.1343 (4) | 0.0581 (4) | 0.1501 (2) | 0.0518 (11) | |
H21D | 0.061 (4) | 0.074 (4) | 0.120 (3) | 0.062* | |
H22D | 0.207 (4) | 0.053 (4) | 0.129 (3) | 0.062* | |
N3D | 0.2671 (3) | 0.1219 (2) | 0.25040 (16) | 0.0270 (7) | |
C4D | 0.2746 (4) | 0.1616 (3) | 0.3159 (2) | 0.0303 (9) | |
N41D | 0.3980 (4) | 0.1822 (3) | 0.3536 (2) | 0.0484 (11) | |
H41D | 0.471 (4) | 0.178 (4) | 0.333 (3) | 0.058* | |
H42D | 0.404 (6) | 0.202 (4) | 0.3982 (18) | 0.058* | |
C5D | 0.1593 (4) | 0.1808 (3) | 0.3453 (2) | 0.0303 (9) | |
H5D | 0.1654 | 0.2088 | 0.3920 | 0.036* | |
C6D | 0.0385 (4) | 0.1578 (3) | 0.3044 (2) | 0.0287 (9) | |
H6D | −0.0411 | 0.1704 | 0.3234 | 0.034* | |
O11X | 1.1290 (4) | 0.1002 (2) | 0.82647 (18) | 0.0494 (8) | |
N2X | 1.0104 (4) | 0.0284 (2) | 0.90302 (17) | 0.0358 (8) | |
C1X | 1.0216 (5) | 0.0701 (3) | 0.8407 (2) | 0.0338 (12) | 0.879 (7) |
H1XA | 0.9422 | 0.0773 | 0.8050 | 0.041* | 0.879 (7) |
C3X | 1.1261 (6) | 0.0079 (4) | 0.9584 (3) | 0.0490 (16) | 0.879 (7) |
H3XA | 1.2087 | 0.0164 | 0.9383 | 0.073* | 0.879 (7) |
H3XB | 1.1209 | −0.0566 | 0.9746 | 0.073* | 0.879 (7) |
H3XC | 1.1275 | 0.0499 | 0.9999 | 0.073* | 0.879 (7) |
C4X | 0.8783 (6) | 0.0015 (4) | 0.9165 (3) | 0.0538 (16) | 0.879 (7) |
H4XA | 0.8102 | 0.0146 | 0.8731 | 0.081* | 0.879 (7) |
H4XB | 0.8574 | 0.0369 | 0.9580 | 0.081* | 0.879 (7) |
H4XC | 0.8781 | −0.0651 | 0.9275 | 0.081* | 0.879 (7) |
C1X' | 1.1258 (19) | 0.049 (3) | 0.8802 (17) | 0.065 (9) | 0.121 (7) |
H1XB | 1.2079 | 0.0228 | 0.9056 | 0.078* | 0.121 (7) |
C3X' | 0.886 (2) | 0.066 (3) | 0.864 (2) | 0.066 (12) | 0.121 (7) |
H3XD | 0.8114 | 0.0446 | 0.8876 | 0.100* | 0.121 (7) |
H3XE | 0.8901 | 0.1337 | 0.8653 | 0.100* | 0.121 (7) |
H3XF | 0.8710 | 0.0439 | 0.8137 | 0.100* | 0.121 (7) |
C4X' | 1.011 (4) | −0.019 (3) | 0.9719 (16) | 0.066 (13) | 0.121 (7) |
H4XD | 0.9183 | −0.0279 | 0.9795 | 0.099* | 0.121 (7) |
H4XE | 1.0550 | −0.0799 | 0.9709 | 0.099* | 0.121 (7) |
H4XF | 1.0612 | 0.0182 | 1.0119 | 0.099* | 0.121 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0252 (18) | 0.0313 (17) | 0.0232 (17) | 0.0029 (15) | 0.0044 (13) | 0.0020 (14) |
C2A | 0.028 (2) | 0.0252 (18) | 0.0243 (18) | 0.0030 (16) | 0.0058 (16) | −0.0037 (15) |
S21A | 0.0274 (5) | 0.0385 (5) | 0.0233 (5) | 0.0057 (4) | 0.0052 (4) | 0.0057 (4) |
N3A | 0.0216 (17) | 0.0308 (17) | 0.0215 (16) | 0.0014 (14) | 0.0057 (13) | 0.0015 (13) |
C4A | 0.031 (2) | 0.0240 (19) | 0.0212 (18) | 0.0028 (17) | 0.0019 (17) | −0.0030 (15) |
O41A | 0.0234 (14) | 0.0428 (17) | 0.0259 (13) | 0.0044 (12) | 0.0026 (11) | 0.0047 (11) |
C5A | 0.028 (2) | 0.0278 (19) | 0.0224 (18) | 0.0012 (16) | 0.0050 (17) | −0.0035 (15) |
C51A | 0.032 (2) | 0.036 (2) | 0.0218 (18) | −0.0005 (18) | 0.0057 (17) | 0.0012 (16) |
C6A | 0.030 (2) | 0.0271 (18) | 0.0217 (18) | 0.0026 (16) | 0.0066 (16) | −0.0010 (15) |
N1C | 0.0267 (18) | 0.0376 (19) | 0.0226 (16) | −0.0013 (15) | 0.0053 (14) | −0.0012 (13) |
C2C | 0.029 (2) | 0.032 (2) | 0.0232 (19) | 0.0000 (17) | 0.0022 (17) | −0.0010 (15) |
N21C | 0.027 (2) | 0.070 (3) | 0.0243 (19) | 0.0012 (19) | −0.0012 (16) | 0.0141 (17) |
N3C | 0.0253 (17) | 0.0316 (17) | 0.0209 (15) | −0.0003 (14) | −0.0002 (14) | 0.0035 (13) |
C4C | 0.030 (2) | 0.0217 (18) | 0.0215 (18) | −0.0018 (16) | 0.0047 (15) | −0.0037 (14) |
N41C | 0.028 (2) | 0.044 (2) | 0.0241 (17) | 0.0018 (16) | 0.0029 (14) | 0.0093 (15) |
C5C | 0.033 (2) | 0.036 (2) | 0.023 (2) | 0.0005 (17) | 0.0072 (18) | 0.0016 (15) |
C6C | 0.029 (2) | 0.037 (2) | 0.029 (2) | −0.0012 (19) | 0.0096 (19) | −0.0034 (17) |
N1B | 0.0246 (18) | 0.0319 (17) | 0.0267 (18) | −0.0024 (15) | 0.0059 (14) | 0.0008 (14) |
C2B | 0.028 (2) | 0.0275 (19) | 0.0232 (18) | −0.0002 (17) | 0.0064 (16) | 0.0024 (15) |
S21B | 0.0266 (5) | 0.0436 (6) | 0.0294 (5) | −0.0037 (5) | 0.0063 (4) | −0.0107 (4) |
N3B | 0.0214 (16) | 0.0305 (17) | 0.0235 (17) | −0.0023 (13) | 0.0052 (14) | −0.0002 (12) |
C4B | 0.028 (2) | 0.030 (2) | 0.0209 (18) | 0.0020 (16) | 0.0021 (17) | 0.0037 (15) |
O41B | 0.0293 (16) | 0.0555 (19) | 0.0270 (14) | −0.0038 (15) | 0.0024 (12) | −0.0057 (13) |
C5B | 0.033 (2) | 0.0279 (19) | 0.0209 (18) | −0.0008 (17) | 0.0062 (16) | 0.0022 (15) |
C51B | 0.041 (3) | 0.036 (2) | 0.025 (2) | 0.0004 (19) | 0.0094 (19) | −0.0004 (17) |
C6B | 0.031 (2) | 0.029 (2) | 0.026 (2) | 0.0006 (16) | 0.0100 (17) | 0.0007 (15) |
N1D | 0.0277 (19) | 0.042 (2) | 0.0241 (16) | −0.0005 (16) | 0.0044 (14) | −0.0013 (14) |
C2D | 0.027 (2) | 0.039 (2) | 0.0222 (19) | 0.0015 (18) | 0.0047 (17) | −0.0002 (16) |
N21D | 0.027 (2) | 0.099 (3) | 0.030 (2) | −0.003 (2) | 0.0063 (16) | −0.025 (2) |
N3D | 0.0237 (17) | 0.0340 (18) | 0.0231 (16) | 0.0025 (14) | 0.0037 (13) | 0.0000 (13) |
C4D | 0.030 (2) | 0.035 (2) | 0.024 (2) | −0.0011 (18) | 0.0005 (17) | −0.0011 (16) |
N41D | 0.029 (2) | 0.086 (3) | 0.030 (2) | −0.004 (2) | 0.0039 (17) | −0.024 (2) |
C5D | 0.030 (2) | 0.040 (2) | 0.0216 (19) | −0.0012 (18) | 0.0066 (18) | −0.0024 (15) |
C6D | 0.028 (2) | 0.033 (2) | 0.026 (2) | 0.0036 (17) | 0.0056 (17) | 0.0005 (16) |
O11X | 0.061 (2) | 0.0503 (18) | 0.0429 (18) | −0.0136 (17) | 0.0251 (16) | −0.0031 (14) |
N2X | 0.043 (2) | 0.0378 (18) | 0.0269 (17) | −0.0040 (16) | 0.0082 (15) | −0.0022 (14) |
C1X | 0.046 (3) | 0.033 (2) | 0.020 (2) | −0.005 (2) | 0.0013 (19) | −0.0027 (18) |
C3X | 0.067 (4) | 0.044 (3) | 0.030 (3) | −0.001 (3) | −0.010 (3) | 0.009 (2) |
C4X | 0.055 (3) | 0.057 (3) | 0.057 (3) | −0.016 (3) | 0.029 (3) | −0.015 (3) |
C1X' | 0.077 (16) | 0.07 (2) | 0.058 (19) | −0.004 (19) | 0.031 (17) | 0.007 (15) |
C3X' | 0.071 (18) | 0.05 (2) | 0.06 (3) | 0.01 (2) | −0.01 (2) | 0.01 (2) |
C4X' | 0.07 (3) | 0.10 (3) | 0.022 (16) | −0.01 (2) | −0.003 (16) | 0.011 (16) |
N1A—C2A | 1.336 (5) | C51B—H51D | 0.9800 |
N1A—C6A | 1.372 (5) | C51B—H51E | 0.9800 |
N1A—H1A | 0.89 (3) | C51B—H51F | 0.9800 |
C2A—N3A | 1.360 (5) | C6B—H6B | 0.9500 |
C2A—S21A | 1.688 (4) | N1D—C2D | 1.337 (5) |
N3A—C4A | 1.396 (5) | N1D—C6D | 1.354 (5) |
N3A—H3A | 0.88 (3) | C2D—N21D | 1.343 (5) |
C4A—O41A | 1.231 (5) | C2D—N3D | 1.352 (5) |
C4A—C5A | 1.433 (6) | N21D—H21D | 0.87 (3) |
C5A—C6A | 1.351 (5) | N21D—H22D | 0.89 (3) |
C5A—C51A | 1.499 (5) | N3D—C4D | 1.338 (5) |
C51A—H51A | 0.9800 | C4D—N41D | 1.345 (6) |
C51A—H51B | 0.9800 | C4D—C5D | 1.399 (6) |
C51A—H51C | 0.9800 | N41D—H41D | 0.89 (3) |
C6A—H6A | 0.9500 | N41D—H42D | 0.87 (3) |
N1C—C2C | 1.339 (6) | C5D—C6D | 1.355 (6) |
N1C—C6C | 1.348 (5) | C5D—H5D | 0.9500 |
C2C—N21C | 1.346 (5) | C6D—H6D | 0.9500 |
C2C—N3C | 1.361 (5) | O11X—C1X | 1.238 (6) |
N21C—H21C | 0.87 (3) | O11X—C1X' | 1.253 (14) |
N21C—H22C | 0.88 (3) | N2X—C1X | 1.330 (5) |
N3C—C4C | 1.345 (5) | N2X—C1X' | 1.340 (13) |
C4C—N41C | 1.349 (5) | N2X—C3X' | 1.433 (13) |
C4C—C5C | 1.400 (6) | N2X—C3X | 1.441 (5) |
N41C—H41C | 0.88 (3) | N2X—C4X | 1.451 (6) |
N41C—H42C | 0.88 (3) | N2X—C4X' | 1.455 (18) |
C5C—C6C | 1.357 (6) | C1X—H1XA | 0.9500 |
C5C—H5C | 0.9500 | C3X—H3XA | 0.9800 |
C6C—H6C | 0.9500 | C3X—H3XB | 0.9800 |
N1B—C2B | 1.343 (5) | C3X—H3XC | 0.9800 |
N1B—C6B | 1.376 (5) | C4X—H4XA | 0.9800 |
N1B—H1B | 0.90 (2) | C4X—H4XB | 0.9800 |
C2B—N3B | 1.368 (5) | C4X—H4XC | 0.9800 |
C2B—S21B | 1.672 (4) | C1X'—H1XB | 0.9500 |
N3B—C4B | 1.387 (5) | C3X'—H3XD | 0.9800 |
N3B—H3B | 0.90 (2) | C3X'—H3XE | 0.9800 |
C4B—O41B | 1.236 (5) | C3X'—H3XF | 0.9800 |
C4B—C5B | 1.437 (6) | C4X'—H4XD | 0.9800 |
C5B—C6B | 1.351 (6) | C4X'—H4XE | 0.9800 |
C5B—C51B | 1.492 (5) | C4X'—H4XF | 0.9800 |
C2A—N1A—C6A | 123.1 (3) | C5B—C51B—H51F | 109.5 |
C2A—N1A—H1A | 119 (3) | H51D—C51B—H51F | 109.5 |
C6A—N1A—H1A | 118 (3) | H51E—C51B—H51F | 109.5 |
N1A—C2A—N3A | 115.4 (3) | C5B—C6B—N1B | 122.5 (4) |
N1A—C2A—S21A | 122.7 (3) | C5B—C6B—H6B | 118.7 |
N3A—C2A—S21A | 121.8 (3) | N1B—C6B—H6B | 118.7 |
C2A—N3A—C4A | 125.8 (3) | C2D—N1D—C6D | 115.5 (3) |
C2A—N3A—H3A | 116 (3) | N1D—C2D—N21D | 117.5 (4) |
C4A—N3A—H3A | 118 (3) | N1D—C2D—N3D | 126.4 (4) |
O41A—C4A—N3A | 119.6 (4) | N21D—C2D—N3D | 116.1 (4) |
O41A—C4A—C5A | 124.7 (3) | C2D—N21D—H21D | 112 (4) |
N3A—C4A—C5A | 115.6 (3) | C2D—N21D—H22D | 121 (4) |
C6A—C5A—C4A | 117.9 (3) | H21D—N21D—H22D | 114 (5) |
C6A—C5A—C51A | 122.8 (4) | C4D—N3D—C2D | 116.0 (3) |
C4A—C5A—C51A | 119.2 (3) | N3D—C4D—N41D | 117.7 (4) |
C5A—C51A—H51A | 109.5 | N3D—C4D—C5D | 121.9 (4) |
C5A—C51A—H51B | 109.5 | N41D—C4D—C5D | 120.4 (4) |
H51A—C51A—H51B | 109.5 | C4D—N41D—H41D | 121 (4) |
C5A—C51A—H51C | 109.5 | C4D—N41D—H42D | 118 (4) |
H51A—C51A—H51C | 109.5 | H41D—N41D—H42D | 121 (5) |
H51B—C51A—H51C | 109.5 | C6D—C5D—C4D | 117.1 (4) |
C5A—C6A—N1A | 122.1 (4) | C6D—C5D—H5D | 121.4 |
C5A—C6A—H6A | 119.0 | C4D—C5D—H5D | 121.4 |
N1A—C6A—H6A | 119.0 | N1D—C6D—C5D | 123.1 (4) |
C2C—N1C—C6C | 115.1 (3) | N1D—C6D—H6D | 118.5 |
N1C—C2C—N21C | 117.9 (4) | C5D—C6D—H6D | 118.5 |
N1C—C2C—N3C | 126.4 (3) | C1X'—N2X—C3X' | 119.4 (16) |
N21C—C2C—N3C | 115.7 (4) | C1X—N2X—C3X | 122.2 (4) |
C2C—N21C—H21C | 127 (4) | C1X—N2X—C4X | 119.8 (4) |
C2C—N21C—H22C | 122 (3) | C3X—N2X—C4X | 118.0 (4) |
H21C—N21C—H22C | 106 (5) | C1X'—N2X—C4X' | 121.0 (16) |
C4C—N3C—C2C | 115.7 (3) | C3X'—N2X—C4X' | 119.0 (18) |
N3C—C4C—N41C | 117.4 (4) | O11X—C1X—N2X | 124.1 (4) |
N3C—C4C—C5C | 122.1 (4) | O11X—C1X—H1XA | 117.9 |
N41C—C4C—C5C | 120.4 (4) | N2X—C1X—H1XA | 117.9 |
C4C—N41C—H41C | 114 (3) | N2X—C3X—H3XA | 109.5 |
C4C—N41C—H42C | 115 (3) | N2X—C3X—H3XB | 109.5 |
H41C—N41C—H42C | 124 (5) | H3XA—C3X—H3XB | 109.5 |
C6C—C5C—C4C | 116.4 (4) | N2X—C3X—H3XC | 109.5 |
C6C—C5C—H5C | 121.8 | H3XA—C3X—H3XC | 109.5 |
C4C—C5C—H5C | 121.8 | H3XB—C3X—H3XC | 109.5 |
N1C—C6C—C5C | 124.2 (4) | N2X—C4X—H4XA | 109.5 |
N1C—C6C—H6C | 117.9 | N2X—C4X—H4XB | 109.5 |
C5C—C6C—H6C | 117.9 | H4XA—C4X—H4XB | 109.5 |
C2B—N1B—C6B | 122.8 (3) | N2X—C4X—H4XC | 109.5 |
C2B—N1B—H1B | 121 (3) | H4XA—C4X—H4XC | 109.5 |
C6B—N1B—H1B | 117 (3) | H4XB—C4X—H4XC | 109.5 |
N1B—C2B—N3B | 115.6 (3) | O11X—C1X'—N2X | 122.1 (15) |
N1B—C2B—S21B | 122.7 (3) | O11X—C1X'—H1XB | 118.9 |
N3B—C2B—S21B | 121.8 (3) | N2X—C1X'—H1XB | 118.9 |
C2B—N3B—C4B | 125.1 (3) | N2X—C3X'—H3XD | 109.5 |
C2B—N3B—H3B | 118 (3) | N2X—C3X'—H3XE | 109.5 |
C4B—N3B—H3B | 117 (3) | H3XD—C3X'—H3XE | 109.5 |
O41B—C4B—N3B | 119.7 (4) | N2X—C3X'—H3XF | 109.5 |
O41B—C4B—C5B | 123.4 (4) | H3XD—C3X'—H3XF | 109.5 |
N3B—C4B—C5B | 116.9 (4) | H3XE—C3X'—H3XF | 109.5 |
C6B—C5B—C4B | 117.0 (3) | N2X—C4X'—H4XD | 109.5 |
C6B—C5B—C51B | 124.3 (4) | N2X—C4X'—H4XE | 109.5 |
C4B—C5B—C51B | 118.7 (4) | H4XD—C4X'—H4XE | 109.5 |
C5B—C51B—H51D | 109.5 | N2X—C4X'—H4XF | 109.5 |
C5B—C51B—H51E | 109.5 | H4XD—C4X'—H4XF | 109.5 |
H51D—C51B—H51E | 109.5 | H4XE—C4X'—H4XF | 109.5 |
C6A—N1A—C2A—N3A | 2.0 (5) | N1B—C2B—N3B—C4B | −3.0 (5) |
C6A—N1A—C2A—S21A | −177.2 (3) | S21B—C2B—N3B—C4B | 176.6 (3) |
N1A—C2A—N3A—C4A | −3.0 (5) | C2B—N3B—C4B—O41B | −179.7 (3) |
S21A—C2A—N3A—C4A | 176.3 (3) | C2B—N3B—C4B—C5B | 1.9 (6) |
C2A—N3A—C4A—O41A | −179.1 (3) | O41B—C4B—C5B—C6B | −177.5 (4) |
C2A—N3A—C4A—C5A | 2.0 (5) | N3B—C4B—C5B—C6B | 0.9 (5) |
O41A—C4A—C5A—C6A | −178.8 (4) | O41B—C4B—C5B—C51B | 2.1 (6) |
N3A—C4A—C5A—C6A | 0.1 (5) | N3B—C4B—C5B—C51B | −179.6 (3) |
O41A—C4A—C5A—C51A | 1.8 (6) | C4B—C5B—C6B—N1B | −2.4 (5) |
N3A—C4A—C5A—C51A | −179.3 (3) | C51B—C5B—C6B—N1B | 178.1 (3) |
C4A—C5A—C6A—N1A | −0.9 (5) | C2B—N1B—C6B—C5B | 1.2 (6) |
C51A—C5A—C6A—N1A | 178.4 (3) | C6D—N1D—C2D—N21D | 177.7 (4) |
C2A—N1A—C6A—C5A | −0.2 (6) | C6D—N1D—C2D—N3D | −1.6 (6) |
C6C—N1C—C2C—N21C | 179.4 (4) | N1D—C2D—N3D—C4D | 1.5 (6) |
C6C—N1C—C2C—N3C | 0.0 (6) | N21D—C2D—N3D—C4D | −177.8 (4) |
N1C—C2C—N3C—C4C | 1.1 (6) | C2D—N3D—C4D—N41D | 178.9 (4) |
N21C—C2C—N3C—C4C | −178.4 (4) | C2D—N3D—C4D—C5D | −0.5 (6) |
C2C—N3C—C4C—N41C | 178.6 (3) | N3D—C4D—C5D—C6D | −0.3 (6) |
C2C—N3C—C4C—C5C | −0.5 (5) | N41D—C4D—C5D—C6D | −179.6 (4) |
N3C—C4C—C5C—C6C | −1.0 (6) | C2D—N1D—C6D—C5D | 0.7 (6) |
N41C—C4C—C5C—C6C | 180.0 (4) | C4D—C5D—C6D—N1D | 0.2 (6) |
C2C—N1C—C6C—C5C | −1.7 (6) | C3X—N2X—C1X—O11X | −4.8 (7) |
C4C—C5C—C6C—N1C | 2.1 (6) | C4X—N2X—C1X—O11X | 175.6 (4) |
C6B—N1B—C2B—N3B | 1.4 (5) | C3X'—N2X—C1X'—O11X | 1 (6) |
C6B—N1B—C2B—S21B | −178.2 (3) | C4X'—N2X—C1X'—O11X | −170 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···N1Ci | 0.89 (3) | 1.95 (3) | 2.841 (5) | 175 (4) |
N3A—H3A···N3C | 0.88 (3) | 2.33 (3) | 3.184 (5) | 165 (4) |
N1B—H1B···N1Dii | 0.90 (2) | 1.98 (3) | 2.881 (5) | 176 (4) |
N3B—H3B···N3D | 0.90 (2) | 2.27 (3) | 3.163 (5) | 173 (4) |
N21C—H21C···O11X | 0.87 (3) | 2.51 (4) | 3.274 (5) | 148 (4) |
N21C—H22C···O41A | 0.88 (3) | 2.03 (3) | 2.897 (5) | 170 (5) |
N41C—H41C···S21A | 0.88 (3) | 2.49 (3) | 3.359 (4) | 167 (4) |
N41C—H42C···O11Xiii | 0.88 (3) | 2.28 (3) | 3.145 (5) | 167 (4) |
N21D—H22D···O41B | 0.89 (3) | 2.00 (3) | 2.876 (5) | 172 (5) |
N41D—H41D···S21B | 0.89 (3) | 2.41 (3) | 3.302 (5) | 175 (5) |
C6A—H6A···O11Xi | 0.95 | 2.45 | 3.368 (5) | 161 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, z−1/2. |
2C9H9N5·2C5H6N2OS·C3H7NO | F(000) = 1536 |
Mr = 731.87 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1237 (13) Å | Cell parameters from 10197 reflections |
b = 19.5259 (14) Å | θ = 3.4–26.1° |
c = 16.7313 (16) Å | µ = 0.21 mm−1 |
β = 100.900 (8)° | T = 173 K |
V = 3568.5 (6) Å3 | Block, colourless |
Z = 4 | 0.29 × 0.21 × 0.14 mm |
STOE IPDS II two-circle diffractometer | 4005 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.122 |
ω scans | θmax = 25.9°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −13→13 |
Tmin = 0.707, Tmax = 1.000 | k = −21→23 |
28366 measured reflections | l = −20→20 |
6888 independent reflections |
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0242P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
6888 reflections | Δρmax = 0.27 e Å−3 |
500 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 | 0.7240 (2) | 0.33781 (12) | 0.35861 (13) | 0.0238 (5) | |
H1A | 0.695 (3) | 0.3342 (16) | 0.3080 (11) | 0.029* | |
C2A | 0.7848 (3) | 0.28178 (14) | 0.39106 (16) | 0.0233 (6) | |
S21A | 0.78557 (8) | 0.20860 (4) | 0.33951 (4) | 0.0321 (2) | |
N3A | 0.8457 (2) | 0.28922 (12) | 0.46960 (13) | 0.0241 (5) | |
H3A | 0.891 (3) | 0.2545 (12) | 0.4926 (17) | 0.029* | |
C4A | 0.8553 (3) | 0.34968 (14) | 0.51513 (16) | 0.0250 (6) | |
O41A | 0.9210 (2) | 0.35168 (11) | 0.58258 (11) | 0.0335 (5) | |
C5A | 0.7859 (3) | 0.40710 (14) | 0.47647 (16) | 0.0243 (6) | |
C51A | 0.7929 (3) | 0.47369 (16) | 0.52174 (18) | 0.0357 (8) | |
H51A | 0.8758 | 0.4925 | 0.5276 | 0.054* | |
H52A | 0.7734 | 0.4660 | 0.5757 | 0.054* | |
H53A | 0.7340 | 0.5061 | 0.4915 | 0.054* | |
C6A | 0.7228 (3) | 0.39836 (15) | 0.39988 (16) | 0.0255 (6) | |
H6A | 0.6759 | 0.4355 | 0.3737 | 0.031* | |
N1C | 1.1528 (2) | 0.14570 (11) | 0.68091 (13) | 0.0234 (5) | |
C2C | 1.0923 (3) | 0.19154 (14) | 0.62862 (16) | 0.0227 (6) | |
N21C | 1.1082 (3) | 0.25761 (12) | 0.64879 (15) | 0.0333 (7) | |
H21C | 1.143 (3) | 0.2653 (17) | 0.6986 (12) | 0.040* | |
H22C | 1.054 (3) | 0.2875 (14) | 0.6270 (18) | 0.040* | |
N3C | 1.0171 (2) | 0.17618 (11) | 0.55747 (12) | 0.0223 (5) | |
C4C | 1.0093 (3) | 0.10863 (14) | 0.54062 (15) | 0.0222 (6) | |
N41C | 0.9375 (2) | 0.08944 (13) | 0.47015 (14) | 0.0301 (6) | |
H41C | 0.905 (3) | 0.1223 (13) | 0.4371 (16) | 0.036* | |
H42C | 0.943 (3) | 0.0461 (10) | 0.4540 (18) | 0.036* | |
N5C | 1.0682 (2) | 0.05846 (11) | 0.58753 (12) | 0.0222 (5) | |
C6C | 1.1378 (2) | 0.08062 (14) | 0.65682 (15) | 0.0204 (6) | |
C7C | 1.2063 (3) | 0.02851 (14) | 0.71324 (15) | 0.0222 (6) | |
C8C | 1.3264 (3) | 0.04220 (15) | 0.75211 (16) | 0.0261 (7) | |
H8C | 1.3655 | 0.0834 | 0.7409 | 0.031* | |
C9C | 1.3883 (3) | −0.00480 (17) | 0.80715 (17) | 0.0343 (8) | |
H9C | 1.4711 | 0.0032 | 0.8321 | 0.041* | |
C10C | 1.3289 (3) | −0.06353 (16) | 0.82574 (18) | 0.0405 (9) | |
H10C | 1.3709 | −0.0950 | 0.8645 | 0.049* | |
C11C | 1.2102 (3) | −0.07673 (16) | 0.78890 (17) | 0.0358 (8) | |
H11C | 1.1702 | −0.1168 | 0.8027 | 0.043* | |
C12C | 1.1484 (3) | −0.03104 (14) | 0.73093 (16) | 0.0268 (7) | |
H12C | 1.0672 | −0.0407 | 0.7038 | 0.032* | |
N1B | 0.3071 (2) | 0.67042 (13) | 0.09829 (15) | 0.0321 (6) | |
H1B | 0.263 (3) | 0.6411 (14) | 0.0672 (17) | 0.039* | |
C2B | 0.3440 (3) | 0.65385 (16) | 0.17798 (19) | 0.0326 (7) | |
S21B | 0.31177 (9) | 0.57761 (4) | 0.21378 (5) | 0.0461 (3) | |
N3B | 0.4072 (2) | 0.70320 (13) | 0.22484 (15) | 0.0315 (6) | |
H3B | 0.433 (3) | 0.6925 (17) | 0.2763 (12) | 0.038* | |
C4B | 0.4289 (3) | 0.76923 (16) | 0.20038 (19) | 0.0325 (7) | |
O41B | 0.4836 (2) | 0.81099 (11) | 0.24972 (14) | 0.0428 (6) | |
C5B | 0.3828 (3) | 0.78429 (16) | 0.11545 (18) | 0.0313 (7) | |
C51B | 0.3956 (3) | 0.85587 (17) | 0.0853 (2) | 0.0394 (8) | |
H51B | 0.3665 | 0.8574 | 0.0262 | 0.059* | |
H52B | 0.4819 | 0.8696 | 0.0979 | 0.059* | |
H53B | 0.3469 | 0.8873 | 0.1119 | 0.059* | |
C6B | 0.3249 (3) | 0.73434 (16) | 0.06820 (19) | 0.0331 (7) | |
H6B | 0.2953 | 0.7434 | 0.0121 | 0.040* | |
N1D | 0.5502 (3) | 0.72591 (13) | 0.53770 (15) | 0.0376 (7) | |
C2D | 0.5200 (3) | 0.72647 (16) | 0.45575 (19) | 0.0397 (9) | |
N21D | 0.5180 (4) | 0.78706 (16) | 0.41994 (18) | 0.0591 (10) | |
H21D | 0.546 (4) | 0.8241 (15) | 0.448 (2) | 0.071* | |
H22D | 0.513 (4) | 0.788 (2) | 0.3662 (12) | 0.071* | |
N3D | 0.4944 (3) | 0.67046 (13) | 0.40835 (15) | 0.0355 (7) | |
C4D | 0.5034 (3) | 0.61157 (16) | 0.45022 (18) | 0.0317 (7) | |
N41D | 0.4798 (3) | 0.55376 (14) | 0.40628 (16) | 0.0391 (7) | |
H41D | 0.451 (3) | 0.5580 (18) | 0.3540 (12) | 0.047* | |
H42D | 0.474 (3) | 0.5131 (12) | 0.4289 (19) | 0.047* | |
N5D | 0.5378 (2) | 0.60452 (13) | 0.53214 (14) | 0.0296 (6) | |
C6D | 0.5584 (3) | 0.66449 (15) | 0.57198 (17) | 0.0279 (7) | |
C7D | 0.5986 (3) | 0.66376 (15) | 0.66242 (17) | 0.0285 (7) | |
C8D | 0.6169 (3) | 0.72528 (16) | 0.70468 (19) | 0.0368 (8) | |
H8D | 0.5980 | 0.7671 | 0.6761 | 0.044* | |
C9D | 0.6622 (3) | 0.72679 (18) | 0.7876 (2) | 0.0434 (9) | |
H9D | 0.6743 | 0.7694 | 0.8155 | 0.052* | |
C10D | 0.6899 (3) | 0.66622 (19) | 0.82988 (19) | 0.0404 (8) | |
H10D | 0.7235 | 0.6670 | 0.8865 | 0.048* | |
C11D | 0.6682 (3) | 0.60473 (18) | 0.78925 (19) | 0.0418 (9) | |
H11D | 0.6832 | 0.5629 | 0.8185 | 0.050* | |
C12D | 0.6247 (3) | 0.60345 (17) | 0.70574 (19) | 0.0379 (8) | |
H12D | 0.6127 | 0.5608 | 0.6781 | 0.045* | |
C1X | 0.1583 (3) | 0.52923 (16) | −0.03270 (18) | 0.0315 (7) | |
H1X | 0.2288 | 0.5039 | −0.0087 | 0.038* | |
O11X | 0.1548 (2) | 0.59035 (11) | −0.01475 (13) | 0.0381 (6) | |
N2X | 0.0709 (2) | 0.49640 (13) | −0.08292 (15) | 0.0326 (6) | |
C3X | −0.0384 (3) | 0.53253 (18) | −0.1233 (2) | 0.0391 (8) | |
H3X1 | −0.0574 | 0.5694 | −0.0880 | 0.059* | |
H3X2 | −0.1073 | 0.5005 | −0.1344 | 0.059* | |
H3X3 | −0.0239 | 0.5520 | −0.1746 | 0.059* | |
C4X | 0.0826 (4) | 0.42428 (18) | −0.1020 (2) | 0.0479 (9) | |
H4X1 | 0.0890 | 0.4195 | −0.1593 | 0.072* | |
H4X2 | 0.0104 | 0.3994 | −0.0920 | 0.072* | |
H4X3 | 0.1562 | 0.4054 | −0.0675 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0297 (14) | 0.0224 (13) | 0.0154 (11) | −0.0009 (11) | −0.0061 (10) | 0.0013 (10) |
C2A | 0.0247 (15) | 0.0212 (15) | 0.0217 (14) | −0.0028 (12) | −0.0019 (11) | 0.0020 (11) |
S21A | 0.0474 (5) | 0.0169 (4) | 0.0247 (4) | 0.0006 (3) | −0.0120 (3) | −0.0006 (3) |
N3A | 0.0296 (14) | 0.0180 (12) | 0.0208 (12) | −0.0007 (11) | −0.0050 (10) | 0.0014 (10) |
C4A | 0.0279 (16) | 0.0243 (16) | 0.0222 (14) | −0.0011 (13) | 0.0030 (12) | 0.0020 (12) |
O41A | 0.0441 (13) | 0.0278 (12) | 0.0217 (10) | 0.0052 (10) | −0.0114 (9) | −0.0017 (8) |
C5A | 0.0246 (15) | 0.0234 (15) | 0.0245 (14) | 0.0023 (12) | 0.0036 (11) | 0.0023 (11) |
C51A | 0.045 (2) | 0.0264 (16) | 0.0295 (16) | 0.0080 (14) | −0.0074 (14) | −0.0041 (13) |
C6A | 0.0262 (16) | 0.0229 (16) | 0.0255 (14) | 0.0020 (12) | −0.0005 (12) | 0.0047 (12) |
N1C | 0.0273 (13) | 0.0189 (12) | 0.0202 (11) | 0.0003 (10) | −0.0055 (10) | −0.0006 (9) |
C2C | 0.0260 (15) | 0.0192 (15) | 0.0211 (13) | −0.0010 (12) | −0.0006 (11) | 0.0017 (11) |
N21C | 0.0485 (17) | 0.0169 (13) | 0.0252 (13) | 0.0025 (12) | −0.0170 (12) | −0.0027 (10) |
N3C | 0.0315 (13) | 0.0164 (12) | 0.0162 (11) | 0.0007 (10) | −0.0025 (9) | −0.0023 (9) |
C4C | 0.0270 (16) | 0.0206 (14) | 0.0180 (13) | −0.0010 (12) | 0.0019 (11) | −0.0029 (11) |
N41C | 0.0439 (16) | 0.0169 (13) | 0.0225 (13) | 0.0020 (11) | −0.0117 (11) | −0.0026 (10) |
N5C | 0.0291 (13) | 0.0179 (12) | 0.0169 (11) | −0.0001 (10) | −0.0024 (10) | −0.0017 (9) |
C6C | 0.0207 (14) | 0.0194 (14) | 0.0198 (13) | 0.0018 (12) | 0.0003 (11) | 0.0000 (11) |
C7C | 0.0287 (16) | 0.0183 (14) | 0.0178 (13) | 0.0070 (12) | −0.0006 (11) | −0.0029 (11) |
C8C | 0.0276 (16) | 0.0242 (15) | 0.0246 (14) | 0.0043 (12) | 0.0002 (12) | −0.0052 (11) |
C9C | 0.0332 (18) | 0.0356 (19) | 0.0289 (16) | 0.0140 (14) | −0.0070 (13) | −0.0060 (13) |
C10C | 0.063 (2) | 0.0298 (18) | 0.0232 (15) | 0.0222 (16) | −0.0057 (15) | 0.0008 (13) |
C11C | 0.059 (2) | 0.0231 (16) | 0.0225 (15) | 0.0035 (16) | 0.0011 (15) | −0.0006 (12) |
C12C | 0.0357 (17) | 0.0192 (15) | 0.0228 (14) | 0.0023 (13) | −0.0013 (12) | −0.0013 (11) |
N1B | 0.0322 (15) | 0.0275 (15) | 0.0337 (14) | −0.0025 (11) | −0.0015 (11) | −0.0036 (11) |
C2B | 0.0266 (17) | 0.0264 (17) | 0.0423 (18) | −0.0010 (13) | 0.0001 (14) | 0.0012 (14) |
S21B | 0.0513 (6) | 0.0265 (4) | 0.0512 (5) | −0.0139 (4) | −0.0142 (4) | 0.0101 (4) |
N3B | 0.0318 (15) | 0.0236 (14) | 0.0355 (14) | −0.0067 (11) | −0.0028 (11) | 0.0026 (11) |
C4B | 0.0319 (18) | 0.0237 (16) | 0.0419 (18) | −0.0013 (13) | 0.0070 (14) | 0.0037 (14) |
O41B | 0.0526 (15) | 0.0276 (12) | 0.0449 (13) | −0.0122 (11) | 0.0007 (11) | 0.0006 (10) |
C5B | 0.0320 (17) | 0.0285 (17) | 0.0349 (16) | 0.0020 (14) | 0.0104 (13) | 0.0025 (14) |
C51B | 0.048 (2) | 0.0267 (17) | 0.0449 (19) | 0.0031 (15) | 0.0115 (16) | 0.0081 (14) |
C6B | 0.0339 (18) | 0.0323 (17) | 0.0341 (17) | 0.0063 (14) | 0.0088 (14) | 0.0023 (14) |
N1D | 0.0449 (17) | 0.0249 (14) | 0.0375 (15) | −0.0037 (12) | −0.0059 (12) | −0.0006 (11) |
C2D | 0.046 (2) | 0.0273 (18) | 0.0384 (18) | −0.0066 (15) | −0.0103 (15) | 0.0063 (14) |
N21D | 0.100 (3) | 0.0249 (16) | 0.0395 (17) | −0.0150 (17) | −0.0194 (18) | 0.0039 (14) |
N3D | 0.0451 (17) | 0.0230 (14) | 0.0328 (14) | −0.0095 (12) | −0.0064 (12) | 0.0051 (11) |
C4D | 0.0312 (18) | 0.0260 (16) | 0.0356 (17) | −0.0051 (13) | 0.0007 (14) | 0.0023 (14) |
N41D | 0.060 (2) | 0.0249 (14) | 0.0278 (14) | −0.0099 (13) | −0.0023 (13) | 0.0027 (11) |
N5D | 0.0298 (14) | 0.0255 (14) | 0.0319 (13) | −0.0049 (11) | 0.0021 (11) | 0.0016 (11) |
C6D | 0.0214 (15) | 0.0262 (16) | 0.0345 (16) | −0.0026 (12) | 0.0011 (12) | 0.0001 (13) |
C7D | 0.0272 (16) | 0.0256 (16) | 0.0330 (16) | −0.0046 (13) | 0.0066 (13) | −0.0022 (13) |
C8D | 0.047 (2) | 0.0263 (17) | 0.0395 (18) | −0.0005 (15) | 0.0143 (15) | 0.0017 (13) |
C9D | 0.058 (2) | 0.038 (2) | 0.0378 (19) | −0.0105 (17) | 0.0173 (17) | −0.0108 (15) |
C10D | 0.043 (2) | 0.051 (2) | 0.0295 (17) | −0.0028 (17) | 0.0126 (15) | −0.0041 (15) |
C11D | 0.050 (2) | 0.0374 (19) | 0.0337 (18) | 0.0032 (16) | −0.0023 (15) | 0.0048 (15) |
C12D | 0.043 (2) | 0.0272 (17) | 0.0386 (18) | 0.0045 (15) | −0.0048 (15) | −0.0011 (14) |
C1X | 0.0332 (18) | 0.0279 (17) | 0.0335 (16) | 0.0003 (14) | 0.0064 (13) | 0.0022 (13) |
O11X | 0.0457 (14) | 0.0250 (12) | 0.0397 (12) | −0.0003 (10) | −0.0022 (10) | −0.0018 (9) |
N2X | 0.0363 (16) | 0.0251 (14) | 0.0371 (14) | −0.0016 (11) | 0.0089 (12) | −0.0017 (11) |
C3X | 0.0358 (19) | 0.0383 (19) | 0.0406 (18) | −0.0042 (15) | 0.0005 (15) | −0.0012 (15) |
C4X | 0.067 (3) | 0.0295 (19) | 0.052 (2) | −0.0021 (18) | 0.0225 (18) | −0.0119 (16) |
N1A—C2A | 1.345 (3) | N3B—H3B | 0.880 (18) |
N1A—C6A | 1.370 (4) | C4B—O41B | 1.236 (4) |
N1A—H1A | 0.849 (17) | C4B—C5B | 1.447 (4) |
C2A—N3A | 1.368 (3) | C5B—C6B | 1.341 (4) |
C2A—S21A | 1.670 (3) | C5B—C51B | 1.502 (4) |
N3A—C4A | 1.398 (4) | C51B—H51B | 0.9800 |
N3A—H3A | 0.890 (18) | C51B—H52B | 0.9800 |
C4A—O41A | 1.224 (3) | C51B—H53B | 0.9800 |
C4A—C5A | 1.443 (4) | C6B—H6B | 0.9500 |
C5A—C6A | 1.351 (4) | N1D—C6D | 1.325 (4) |
C5A—C51A | 1.499 (4) | N1D—C2D | 1.349 (4) |
C51A—H51A | 0.9800 | C2D—N21D | 1.324 (4) |
C51A—H52A | 0.9800 | C2D—N3D | 1.349 (4) |
C51A—H53A | 0.9800 | N21D—H21D | 0.886 (19) |
C6A—H6A | 0.9500 | N21D—H22D | 0.891 (19) |
N1C—C6C | 1.334 (3) | N3D—C4D | 1.340 (4) |
N1C—C2C | 1.340 (3) | C4D—N41D | 1.345 (4) |
C2C—N21C | 1.337 (4) | C4D—N5D | 1.359 (4) |
C2C—N3C | 1.353 (3) | N41D—H41D | 0.877 (18) |
N21C—H21C | 0.864 (18) | N41D—H42D | 0.887 (18) |
N21C—H22C | 0.870 (18) | N5D—C6D | 1.345 (4) |
N3C—C4C | 1.348 (3) | C6D—C7D | 1.495 (4) |
C4C—N5C | 1.345 (3) | C7D—C12D | 1.384 (4) |
C4C—N41C | 1.346 (3) | C7D—C8D | 1.389 (4) |
N41C—H41C | 0.879 (18) | C8D—C9D | 1.384 (5) |
N41C—H42C | 0.895 (18) | C8D—H8D | 0.9500 |
N5C—C6C | 1.339 (3) | C9D—C10D | 1.382 (5) |
C6C—C7C | 1.495 (4) | C9D—H9D | 0.9500 |
C7C—C12C | 1.388 (4) | C10D—C11D | 1.378 (5) |
C7C—C8C | 1.397 (4) | C10D—H10D | 0.9500 |
C8C—C9C | 1.387 (4) | C11D—C12D | 1.390 (4) |
C8C—H8C | 0.9500 | C11D—H11D | 0.9500 |
C9C—C10C | 1.388 (5) | C12D—H12D | 0.9500 |
C9C—H9C | 0.9500 | C1X—O11X | 1.233 (4) |
C10C—C11C | 1.371 (5) | C1X—N2X | 1.323 (4) |
C10C—H10C | 0.9500 | C1X—H1X | 0.9500 |
C11C—C12C | 1.399 (4) | N2X—C4X | 1.455 (4) |
C11C—H11C | 0.9500 | N2X—C3X | 1.457 (4) |
C12C—H12C | 0.9500 | C3X—H3X1 | 0.9800 |
N1B—C2B | 1.358 (4) | C3X—H3X2 | 0.9800 |
N1B—C6B | 1.374 (4) | C3X—H3X3 | 0.9800 |
N1B—H1B | 0.862 (18) | C4X—H4X1 | 0.9800 |
C2B—N3B | 1.353 (4) | C4X—H4X2 | 0.9800 |
C2B—S21B | 1.669 (3) | C4X—H4X3 | 0.9800 |
N3B—C4B | 1.388 (4) | ||
C2A—N1A—C6A | 123.4 (2) | O41B—C4B—N3B | 120.5 (3) |
C2A—N1A—H1A | 114 (2) | O41B—C4B—C5B | 124.1 (3) |
C6A—N1A—H1A | 122 (2) | N3B—C4B—C5B | 115.4 (3) |
N1A—C2A—N3A | 114.9 (2) | C6B—C5B—C4B | 118.2 (3) |
N1A—C2A—S21A | 122.59 (19) | C6B—C5B—C51B | 123.0 (3) |
N3A—C2A—S21A | 122.5 (2) | C4B—C5B—C51B | 118.7 (3) |
C2A—N3A—C4A | 125.9 (2) | C5B—C51B—H51B | 109.5 |
C2A—N3A—H3A | 118.2 (19) | C5B—C51B—H52B | 109.5 |
C4A—N3A—H3A | 115.5 (19) | H51B—C51B—H52B | 109.5 |
O41A—C4A—N3A | 120.0 (2) | C5B—C51B—H53B | 109.5 |
O41A—C4A—C5A | 124.3 (3) | H51B—C51B—H53B | 109.5 |
N3A—C4A—C5A | 115.6 (2) | H52B—C51B—H53B | 109.5 |
C6A—C5A—C4A | 117.7 (3) | C5B—C6B—N1B | 122.1 (3) |
C6A—C5A—C51A | 123.8 (3) | C5B—C6B—H6B | 119.0 |
C4A—C5A—C51A | 118.4 (2) | N1B—C6B—H6B | 119.0 |
C5A—C51A—H51A | 109.5 | C6D—N1D—C2D | 115.5 (3) |
C5A—C51A—H52A | 109.5 | N21D—C2D—N1D | 116.5 (3) |
H51A—C51A—H52A | 109.5 | N21D—C2D—N3D | 118.3 (3) |
C5A—C51A—H53A | 109.5 | N1D—C2D—N3D | 125.1 (3) |
H51A—C51A—H53A | 109.5 | C2D—N21D—H21D | 121 (3) |
H52A—C51A—H53A | 109.5 | C2D—N21D—H22D | 118 (3) |
C5A—C6A—N1A | 122.3 (3) | H21D—N21D—H22D | 118 (4) |
C5A—C6A—H6A | 118.9 | C4D—N3D—C2D | 113.7 (3) |
N1A—C6A—H6A | 118.9 | N3D—C4D—N41D | 116.5 (3) |
C6C—N1C—C2C | 114.9 (2) | N3D—C4D—N5D | 126.4 (3) |
N21C—C2C—N1C | 117.0 (2) | N41D—C4D—N5D | 117.1 (3) |
N21C—C2C—N3C | 117.8 (2) | C4D—N41D—H41D | 118 (2) |
N1C—C2C—N3C | 125.2 (2) | C4D—N41D—H42D | 123 (2) |
C2C—N21C—H21C | 115 (2) | H41D—N41D—H42D | 118 (3) |
C2C—N21C—H22C | 120 (2) | C6D—N5D—C4D | 113.6 (3) |
H21C—N21C—H22C | 116 (3) | N1D—C6D—N5D | 125.6 (3) |
C4C—N3C—C2C | 113.9 (2) | N1D—C6D—C7D | 115.4 (3) |
N5C—C4C—N41C | 116.8 (2) | N5D—C6D—C7D | 118.9 (3) |
N5C—C4C—N3C | 125.8 (2) | C12D—C7D—C8D | 118.2 (3) |
N41C—C4C—N3C | 117.3 (2) | C12D—C7D—C6D | 122.1 (3) |
C4C—N41C—H41C | 117 (2) | C8D—C7D—C6D | 119.6 (3) |
C4C—N41C—H42C | 118 (2) | C9D—C8D—C7D | 121.3 (3) |
H41C—N41C—H42C | 123 (3) | C9D—C8D—H8D | 119.4 |
C6C—N5C—C4C | 114.1 (2) | C7D—C8D—H8D | 119.4 |
N1C—C6C—N5C | 126.0 (2) | C10D—C9D—C8D | 119.9 (3) |
N1C—C6C—C7C | 116.0 (2) | C10D—C9D—H9D | 120.1 |
N5C—C6C—C7C | 118.0 (2) | C8D—C9D—H9D | 120.1 |
C12C—C7C—C8C | 120.2 (2) | C11D—C10D—C9D | 119.5 (3) |
C12C—C7C—C6C | 120.2 (2) | C11D—C10D—H10D | 120.3 |
C8C—C7C—C6C | 119.5 (3) | C9D—C10D—H10D | 120.3 |
C9C—C8C—C7C | 119.6 (3) | C10D—C11D—C12D | 120.4 (3) |
C9C—C8C—H8C | 120.2 | C10D—C11D—H11D | 119.8 |
C7C—C8C—H8C | 120.2 | C12D—C11D—H11D | 119.8 |
C8C—C9C—C10C | 119.9 (3) | C7D—C12D—C11D | 120.6 (3) |
C8C—C9C—H9C | 120.1 | C7D—C12D—H12D | 119.7 |
C10C—C9C—H9C | 120.1 | C11D—C12D—H12D | 119.7 |
C11C—C10C—C9C | 120.9 (3) | O11X—C1X—N2X | 124.8 (3) |
C11C—C10C—H10C | 119.6 | O11X—C1X—H1X | 117.6 |
C9C—C10C—H10C | 119.6 | N2X—C1X—H1X | 117.6 |
C10C—C11C—C12C | 119.8 (3) | C1X—N2X—C4X | 121.5 (3) |
C10C—C11C—H11C | 120.1 | C1X—N2X—C3X | 120.5 (3) |
C12C—C11C—H11C | 120.1 | C4X—N2X—C3X | 117.9 (3) |
C7C—C12C—C11C | 119.6 (3) | N2X—C3X—H3X1 | 109.5 |
C7C—C12C—H12C | 120.2 | N2X—C3X—H3X2 | 109.5 |
C11C—C12C—H12C | 120.2 | H3X1—C3X—H3X2 | 109.5 |
C2B—N1B—C6B | 122.6 (3) | N2X—C3X—H3X3 | 109.5 |
C2B—N1B—H1B | 118 (2) | H3X1—C3X—H3X3 | 109.5 |
C6B—N1B—H1B | 119 (2) | H3X2—C3X—H3X3 | 109.5 |
N3B—C2B—N1B | 115.3 (3) | N2X—C4X—H4X1 | 109.5 |
N3B—C2B—S21B | 123.4 (2) | N2X—C4X—H4X2 | 109.5 |
N1B—C2B—S21B | 121.3 (2) | H4X1—C4X—H4X2 | 109.5 |
C2B—N3B—C4B | 126.3 (3) | N2X—C4X—H4X3 | 109.5 |
C2B—N3B—H3B | 116 (2) | H4X1—C4X—H4X3 | 109.5 |
C4B—N3B—H3B | 118 (2) | H4X2—C4X—H4X3 | 109.5 |
C6A—N1A—C2A—N3A | 0.5 (4) | C6B—N1B—C2B—S21B | 175.4 (3) |
C6A—N1A—C2A—S21A | −179.7 (2) | N1B—C2B—N3B—C4B | 5.1 (5) |
N1A—C2A—N3A—C4A | −4.1 (4) | S21B—C2B—N3B—C4B | −174.7 (3) |
S21A—C2A—N3A—C4A | 176.1 (2) | C2B—N3B—C4B—O41B | 176.9 (3) |
C2A—N3A—C4A—O41A | −173.7 (3) | C2B—N3B—C4B—C5B | −2.8 (5) |
C2A—N3A—C4A—C5A | 5.1 (4) | O41B—C4B—C5B—C6B | 179.9 (3) |
O41A—C4A—C5A—C6A | 176.3 (3) | N3B—C4B—C5B—C6B | −0.4 (5) |
N3A—C4A—C5A—C6A | −2.5 (4) | O41B—C4B—C5B—C51B | −3.3 (5) |
O41A—C4A—C5A—C51A | −0.8 (5) | N3B—C4B—C5B—C51B | 176.3 (3) |
N3A—C4A—C5A—C51A | −179.6 (3) | C4B—C5B—C6B—N1B | 1.0 (5) |
C4A—C5A—C6A—N1A | −0.7 (4) | C51B—C5B—C6B—N1B | −175.6 (3) |
C51A—C5A—C6A—N1A | 176.2 (3) | C2B—N1B—C6B—C5B | 1.6 (5) |
C2A—N1A—C6A—C5A | 1.8 (5) | C6D—N1D—C2D—N21D | −176.4 (4) |
C6C—N1C—C2C—N21C | −177.6 (3) | C6D—N1D—C2D—N3D | 2.3 (5) |
C6C—N1C—C2C—N3C | 2.4 (4) | N21D—C2D—N3D—C4D | 177.6 (4) |
N21C—C2C—N3C—C4C | 178.0 (3) | N1D—C2D—N3D—C4D | −1.0 (5) |
N1C—C2C—N3C—C4C | −2.0 (4) | C2D—N3D—C4D—N41D | −179.6 (3) |
C2C—N3C—C4C—N5C | 0.1 (4) | C2D—N3D—C4D—N5D | −1.8 (5) |
C2C—N3C—C4C—N41C | −179.0 (3) | N3D—C4D—N5D—C6D | 3.1 (5) |
N41C—C4C—N5C—C6C | −179.8 (3) | N41D—C4D—N5D—C6D | −179.2 (3) |
N3C—C4C—N5C—C6C | 1.0 (4) | C2D—N1D—C6D—N5D | −0.9 (5) |
C2C—N1C—C6C—N5C | −1.0 (4) | C2D—N1D—C6D—C7D | 176.7 (3) |
C2C—N1C—C6C—C7C | 178.8 (3) | C4D—N5D—C6D—N1D | −1.6 (5) |
C4C—N5C—C6C—N1C | −0.5 (4) | C4D—N5D—C6D—C7D | −179.1 (3) |
C4C—N5C—C6C—C7C | 179.7 (3) | N1D—C6D—C7D—C12D | −172.6 (3) |
N1C—C6C—C7C—C12C | 135.0 (3) | N5D—C6D—C7D—C12D | 5.2 (4) |
N5C—C6C—C7C—C12C | −45.2 (4) | N1D—C6D—C7D—C8D | 4.0 (4) |
N1C—C6C—C7C—C8C | −40.8 (4) | N5D—C6D—C7D—C8D | −178.2 (3) |
N5C—C6C—C7C—C8C | 139.0 (3) | C12D—C7D—C8D—C9D | 1.2 (5) |
C12C—C7C—C8C—C9C | 1.4 (4) | C6D—C7D—C8D—C9D | −175.5 (3) |
C6C—C7C—C8C—C9C | 177.2 (3) | C7D—C8D—C9D—C10D | −0.2 (5) |
C7C—C8C—C9C—C10C | −2.7 (5) | C8D—C9D—C10D—C11D | −2.1 (5) |
C8C—C9C—C10C—C11C | 1.6 (5) | C9D—C10D—C11D—C12D | 3.2 (6) |
C9C—C10C—C11C—C12C | 0.9 (5) | C8D—C7D—C12D—C11D | −0.1 (5) |
C8C—C7C—C12C—C11C | 1.1 (4) | C6D—C7D—C12D—C11D | 176.5 (3) |
C6C—C7C—C12C—C11C | −174.7 (3) | C10D—C11D—C12D—C7D | −2.1 (6) |
C10C—C11C—C12C—C7C | −2.2 (5) | O11X—C1X—N2X—C4X | 179.1 (3) |
C6B—N1B—C2B—N3B | −4.4 (5) | O11X—C1X—N2X—C3X | 1.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···N1Ci | 0.85 (2) | 2.13 (2) | 2.946 (3) | 162 (3) |
N3A—H3A···N3C | 0.89 (2) | 2.21 (2) | 3.099 (3) | 174 (3) |
N1B—H1B···O11X | 0.86 (2) | 1.92 (2) | 2.771 (3) | 169 (3) |
N3B—H3B···N3D | 0.88 (2) | 2.23 (2) | 3.107 (3) | 177 (3) |
N21C—H21C···S21Aii | 0.86 (2) | 2.63 (2) | 3.483 (2) | 170 (3) |
N21C—H22C···O41A | 0.87 (2) | 1.97 (2) | 2.840 (3) | 175 (3) |
N41C—H41C···S21A | 0.88 (2) | 2.54 (2) | 3.413 (2) | 173 (3) |
N41C—H42C···N5Ciii | 0.90 (2) | 2.15 (2) | 3.042 (3) | 173 (3) |
N21D—H21D···O11Xiv | 0.89 (2) | 2.09 (2) | 2.934 (4) | 159 (4) |
N21D—H22D···O41B | 0.89 (2) | 1.96 (2) | 2.840 (4) | 167 (4) |
N41D—H41D···S21B | 0.88 (2) | 2.58 (2) | 3.436 (3) | 165 (3) |
N41D—H42D···N5Dv | 0.89 (2) | 2.40 (2) | 3.275 (4) | 170 (3) |
C10C—H10C···O41Avi | 0.95 | 2.54 | 3.350 (4) | 143 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+2, −y, −z+1; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+1, −y+1, −z+1; (vi) −x+5/2, y−1/2, −z+3/2. |
2C5H6N2OS·2C4H6N4O·C3H7NO | F(000) = 1280 |
Mr = 609.71 | Dx = 1.423 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.573 (3) Å | Cell parameters from 13239 reflections |
b = 9.1593 (12) Å | θ = 3.2–26.2° |
c = 13.9211 (16) Å | µ = 0.25 mm−1 |
β = 98.701 (10)° | T = 173 K |
V = 2845.1 (6) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.10 × 0.07 mm |
STOE IPDS II two-circle diffractometer | 2052 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.122 |
ω scans | θmax = 25.9°, θmin = 3.2° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −27→27 |
Tmin = 0.362, Tmax = 1.000 | k = −10→11 |
11737 measured reflections | l = −16→17 |
2741 independent reflections |
Refinement on F2 | 15 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0529P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2741 reflections | Δρmax = 0.47 e Å−3 |
228 parameters | Δρmin = −0.21 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 | Occ. (<1) | |
N1A | 0.25804 (9) | 0.5870 (2) | 0.68791 (13) | 0.0276 (4) | |
H1A | 0.2737 (12) | 0.590 (3) | 0.7497 (13) | 0.033* | |
C2A | 0.28461 (10) | 0.5045 (3) | 0.62657 (15) | 0.0250 (5) | |
S21A | 0.34920 (3) | 0.41635 (8) | 0.66439 (4) | 0.0320 (2) | |
N3A | 0.25635 (9) | 0.5023 (2) | 0.53334 (13) | 0.0265 (4) | |
H3A | 0.2719 (12) | 0.450 (3) | 0.4914 (18) | 0.032* | |
C4A | 0.20409 (11) | 0.5776 (3) | 0.49760 (16) | 0.0283 (5) | |
O41A | 0.18212 (9) | 0.5617 (2) | 0.41215 (12) | 0.0414 (5) | |
C5A | 0.18093 (11) | 0.6718 (3) | 0.56548 (18) | 0.0306 (6) | |
C51A | 0.12694 (13) | 0.7639 (3) | 0.5318 (2) | 0.0441 (7) | |
H51A | 0.1187 | 0.8270 | 0.5851 | 0.066* | |
H51B | 0.0923 | 0.7006 | 0.5115 | 0.066* | |
H51C | 0.1345 | 0.8243 | 0.4769 | 0.066* | |
C6A | 0.20850 (11) | 0.6704 (3) | 0.65809 (17) | 0.0308 (6) | |
H6A | 0.1929 | 0.7295 | 0.7045 | 0.037* | |
N1B | 0.43554 (9) | 0.0600 (2) | 0.40837 (13) | 0.0267 (5) | |
C2B | 0.42522 (10) | 0.1474 (3) | 0.47932 (15) | 0.0249 (5) | |
N21B | 0.46111 (10) | 0.1394 (3) | 0.56472 (14) | 0.0340 (5) | |
H21B | 0.4922 (11) | 0.080 (3) | 0.570 (2) | 0.041* | |
H22B | 0.4568 (14) | 0.202 (3) | 0.6102 (18) | 0.041* | |
N3B | 0.38020 (9) | 0.2451 (2) | 0.46922 (13) | 0.0282 (5) | |
H3B | 0.3711 (12) | 0.292 (3) | 0.5202 (17) | 0.034* | |
C4B | 0.34121 (11) | 0.2632 (3) | 0.38263 (15) | 0.0269 (5) | |
O41B | 0.30123 (8) | 0.3593 (2) | 0.38019 (11) | 0.0332 (4) | |
C5B | 0.35140 (11) | 0.1717 (3) | 0.30740 (15) | 0.0282 (5) | |
H5B | 0.3267 | 0.1775 | 0.2459 | 0.034* | |
C6B | 0.39779 (11) | 0.0719 (3) | 0.32273 (16) | 0.0283 (5) | |
N61B | 0.40827 (11) | −0.0195 (3) | 0.25269 (15) | 0.0380 (6) | |
H61B | 0.3866 (12) | −0.010 (4) | 0.1959 (15) | 0.046* | |
H62B | 0.4333 (13) | −0.090 (3) | 0.263 (2) | 0.046* | |
O11X | 0.5000 | 0.2887 (3) | 0.7500 | 0.0411 (7) | |
N2X | 0.4953 (12) | 0.5328 (5) | 0.7625 (11) | 0.050 (2) | 0.5 |
C1X | 0.5071 (3) | 0.4131 (5) | 0.7191 (4) | 0.0373 (12) | 0.5 |
H1X | 0.5223 | 0.4217 | 0.6593 | 0.045* | 0.5 |
C3X | 0.4846 (3) | 0.5240 (8) | 0.8626 (5) | 0.0565 (17) | 0.5 |
H3XA | 0.5118 | 0.5906 | 0.9029 | 0.085* | 0.5 |
H3XB | 0.4917 | 0.4238 | 0.8863 | 0.085* | 0.5 |
H3XC | 0.4430 | 0.5515 | 0.8660 | 0.085* | 0.5 |
C4X | 0.4965 (5) | 0.6753 (7) | 0.7160 (6) | 0.074 (3) | 0.5 |
H4XA | 0.4566 | 0.7195 | 0.7092 | 0.112* | 0.5 |
H4XB | 0.5085 | 0.6635 | 0.6516 | 0.112* | 0.5 |
H4XC | 0.5254 | 0.7387 | 0.7560 | 0.112* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0283 (10) | 0.0340 (12) | 0.0188 (9) | −0.0052 (9) | −0.0018 (8) | −0.0044 (9) |
C2A | 0.0257 (12) | 0.0288 (13) | 0.0193 (10) | −0.0077 (10) | −0.0006 (9) | −0.0004 (10) |
S21A | 0.0282 (3) | 0.0450 (4) | 0.0201 (3) | 0.0047 (3) | −0.0050 (2) | 0.0019 (3) |
N3A | 0.0284 (11) | 0.0321 (12) | 0.0170 (9) | 0.0003 (9) | −0.0025 (8) | −0.0029 (8) |
C4A | 0.0255 (12) | 0.0322 (14) | 0.0246 (11) | −0.0051 (10) | −0.0048 (9) | 0.0024 (10) |
O41A | 0.0390 (11) | 0.0571 (13) | 0.0232 (8) | 0.0018 (9) | −0.0109 (7) | 0.0003 (9) |
C5A | 0.0254 (12) | 0.0317 (14) | 0.0334 (12) | −0.0037 (10) | 0.0004 (10) | 0.0026 (11) |
C51A | 0.0345 (15) | 0.0459 (18) | 0.0503 (16) | 0.0053 (13) | 0.0013 (12) | 0.0098 (14) |
C6A | 0.0303 (13) | 0.0326 (14) | 0.0291 (12) | −0.0024 (10) | 0.0033 (10) | −0.0066 (11) |
N1B | 0.0283 (11) | 0.0307 (12) | 0.0184 (9) | 0.0027 (8) | −0.0057 (8) | −0.0021 (8) |
C2B | 0.0250 (11) | 0.0297 (13) | 0.0186 (10) | −0.0014 (10) | −0.0015 (8) | 0.0025 (9) |
N21B | 0.0388 (12) | 0.0416 (14) | 0.0177 (9) | 0.0112 (10) | −0.0079 (9) | −0.0054 (9) |
N3B | 0.0323 (11) | 0.0350 (12) | 0.0152 (8) | 0.0050 (9) | −0.0029 (8) | −0.0020 (8) |
C4B | 0.0284 (12) | 0.0314 (14) | 0.0187 (10) | 0.0001 (10) | −0.0034 (9) | 0.0050 (10) |
O41B | 0.0359 (9) | 0.0408 (11) | 0.0202 (8) | 0.0131 (8) | −0.0045 (7) | 0.0006 (7) |
C5B | 0.0314 (13) | 0.0341 (14) | 0.0161 (10) | 0.0040 (10) | −0.0062 (9) | −0.0002 (10) |
C6B | 0.0295 (13) | 0.0331 (14) | 0.0202 (10) | 0.0018 (11) | −0.0036 (9) | −0.0013 (10) |
N61B | 0.0422 (13) | 0.0468 (15) | 0.0206 (10) | 0.0169 (11) | −0.0097 (9) | −0.0100 (10) |
O11X | 0.0599 (18) | 0.0333 (17) | 0.0253 (12) | 0.000 | −0.0091 (12) | 0.000 |
N2X | 0.026 (7) | 0.038 (3) | 0.088 (7) | −0.003 (3) | 0.016 (5) | −0.004 (4) |
C1X | 0.039 (3) | 0.034 (3) | 0.036 (3) | −0.001 (3) | −0.004 (2) | 0.010 (2) |
C3X | 0.063 (4) | 0.047 (4) | 0.061 (4) | 0.000 (3) | 0.013 (3) | −0.019 (3) |
C4X | 0.090 (6) | 0.031 (3) | 0.102 (7) | −0.006 (4) | 0.014 (8) | 0.014 (3) |
N1A—C2A | 1.347 (3) | N3B—C4B | 1.391 (3) |
N1A—C6A | 1.366 (3) | N3B—H3B | 0.882 (17) |
N1A—H1A | 0.880 (18) | C4B—O41B | 1.257 (3) |
C2A—N3A | 1.357 (3) | C4B—C5B | 1.388 (3) |
C2A—S21A | 1.680 (3) | C5B—C6B | 1.381 (4) |
N3A—C4A | 1.392 (3) | C5B—H5B | 0.9500 |
N3A—H3A | 0.872 (17) | C6B—N61B | 1.334 (3) |
C4A—O41A | 1.226 (3) | N61B—H61B | 0.869 (18) |
C4A—C5A | 1.435 (4) | N61B—H62B | 0.855 (18) |
C5A—C6A | 1.344 (4) | O11X—C1X | 1.237 (5) |
C5A—C51A | 1.498 (4) | N2X—C1X | 1.299 (7) |
C51A—H51A | 0.9800 | N2X—C3X | 1.452 (9) |
C51A—H51B | 0.9800 | N2X—C4X | 1.459 (9) |
C51A—H51C | 0.9800 | C1X—H1X | 0.9500 |
C6A—H6A | 0.9500 | C3X—H3XA | 0.9800 |
N1B—C2B | 1.319 (3) | C3X—H3XB | 0.9800 |
N1B—C6B | 1.361 (3) | C3X—H3XC | 0.9800 |
C2B—N21B | 1.336 (3) | C4X—H4XA | 0.9800 |
C2B—N3B | 1.345 (3) | C4X—H4XB | 0.9800 |
N21B—H21B | 0.881 (18) | C4X—H4XC | 0.9800 |
N21B—H22B | 0.867 (18) | ||
C2A—N1A—C6A | 122.9 (2) | C2B—N3B—H3B | 120.5 (19) |
C2A—N1A—H1A | 118.9 (19) | C4B—N3B—H3B | 116.4 (19) |
C6A—N1A—H1A | 118.2 (19) | O41B—C4B—C5B | 127.1 (2) |
N1A—C2A—N3A | 115.1 (2) | O41B—C4B—N3B | 117.7 (2) |
N1A—C2A—S21A | 121.29 (17) | C5B—C4B—N3B | 115.2 (2) |
N3A—C2A—S21A | 123.56 (18) | C6B—C5B—C4B | 119.4 (2) |
C2A—N3A—C4A | 125.8 (2) | C6B—C5B—H5B | 120.3 |
C2A—N3A—H3A | 118 (2) | C4B—C5B—H5B | 120.3 |
C4A—N3A—H3A | 116 (2) | N61B—C6B—N1B | 115.7 (2) |
O41A—C4A—N3A | 119.0 (2) | N61B—C6B—C5B | 121.1 (2) |
O41A—C4A—C5A | 125.2 (2) | N1B—C6B—C5B | 123.2 (2) |
N3A—C4A—C5A | 115.9 (2) | C6B—N61B—H61B | 118 (2) |
C6A—C5A—C4A | 117.6 (2) | C6B—N61B—H62B | 123 (2) |
C6A—C5A—C51A | 122.8 (3) | H61B—N61B—H62B | 119 (3) |
C4A—C5A—C51A | 119.5 (2) | C1X—N2X—C3X | 118.4 (7) |
C5A—C51A—H51A | 109.5 | C1X—N2X—C4X | 122.0 (8) |
C5A—C51A—H51B | 109.5 | C3X—N2X—C4X | 119.5 (6) |
H51A—C51A—H51B | 109.5 | O11X—C1X—N2X | 124.7 (5) |
C5A—C51A—H51C | 109.5 | O11X—C1X—H1X | 117.7 |
H51A—C51A—H51C | 109.5 | N2X—C1X—H1X | 117.7 |
H51B—C51A—H51C | 109.5 | N2X—C3X—H3XA | 109.5 |
C5A—C6A—N1A | 122.4 (2) | N2X—C3X—H3XB | 109.5 |
C5A—C6A—H6A | 118.8 | H3XA—C3X—H3XB | 109.5 |
N1A—C6A—H6A | 118.8 | N2X—C3X—H3XC | 109.5 |
C2B—N1B—C6B | 116.7 (2) | H3XA—C3X—H3XC | 109.5 |
N1B—C2B—N21B | 118.8 (2) | H3XB—C3X—H3XC | 109.5 |
N1B—C2B—N3B | 122.8 (2) | N2X—C4X—H4XA | 109.5 |
N21B—C2B—N3B | 118.5 (2) | N2X—C4X—H4XB | 109.5 |
C2B—N21B—H21B | 119 (2) | H4XA—C4X—H4XB | 109.5 |
C2B—N21B—H22B | 120 (2) | N2X—C4X—H4XC | 109.5 |
H21B—N21B—H22B | 121 (3) | H4XA—C4X—H4XC | 109.5 |
C2B—N3B—C4B | 122.6 (2) | H4XB—C4X—H4XC | 109.5 |
C6A—N1A—C2A—N3A | −4.1 (3) | C6B—N1B—C2B—N3B | −0.4 (3) |
C6A—N1A—C2A—S21A | 174.07 (19) | N1B—C2B—N3B—C4B | −0.8 (4) |
N1A—C2A—N3A—C4A | 0.7 (4) | N21B—C2B—N3B—C4B | 178.8 (2) |
S21A—C2A—N3A—C4A | −177.5 (2) | C2B—N3B—C4B—O41B | −178.8 (2) |
C2A—N3A—C4A—O41A | −177.4 (2) | C2B—N3B—C4B—C5B | 0.9 (3) |
C2A—N3A—C4A—C5A | 3.9 (4) | O41B—C4B—C5B—C6B | 179.8 (3) |
O41A—C4A—C5A—C6A | 176.3 (3) | N3B—C4B—C5B—C6B | 0.1 (3) |
N3A—C4A—C5A—C6A | −5.1 (3) | C2B—N1B—C6B—N61B | −178.6 (2) |
O41A—C4A—C5A—C51A | −2.2 (4) | C2B—N1B—C6B—C5B | 1.5 (4) |
N3A—C4A—C5A—C51A | 176.4 (2) | C4B—C5B—C6B—N61B | 178.8 (3) |
C4A—C5A—C6A—N1A | 2.1 (4) | C4B—C5B—C6B—N1B | −1.4 (4) |
C51A—C5A—C6A—N1A | −179.4 (2) | C3X—N2X—C1X—O11X | 13 (3) |
C2A—N1A—C6A—C5A | 2.8 (4) | C4X—N2X—C1X—O11X | −171.1 (13) |
C6B—N1B—C2B—N21B | 179.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O41Bi | 0.88 (2) | 1.89 (2) | 2.751 (2) | 167 (3) |
N3A—H3A···O41B | 0.87 (2) | 1.96 (2) | 2.818 (3) | 169 (3) |
N21B—H21B···N1Bii | 0.88 (2) | 2.06 (2) | 2.942 (3) | 177 (3) |
N21B—H22B···O11X | 0.87 (2) | 2.19 (2) | 2.934 (2) | 143 (3) |
N3B—H3B···S21A | 0.88 (2) | 2.42 (2) | 3.303 (2) | 178 (3) |
C5B—H5B···O41Aiii | 0.95 | 2.42 | 3.198 (3) | 139 |
N61B—H61B···O41Aiii | 0.87 (2) | 2.10 (2) | 2.927 (3) | 160 (3) |
N61B—H62B···O11Xii | 0.86 (2) | 2.39 (2) | 3.223 (3) | 166 (3) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, −z+1/2. |
2C5H6N2OS·2C4H6N4O·C4H9NO | F(000) = 1312 |
Mr = 623.73 | Dx = 1.449 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.530 (3) Å | Cell parameters from 9945 reflections |
b = 8.7478 (9) Å | θ = 3.5–26.1° |
c = 14.2006 (16) Å | µ = 0.25 mm−1 |
β = 102.037 (10)° | T = 173 K |
V = 2858.7 (6) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.21 × 0.16 mm |
STOE IPDS II two-circle diffractometer | 1896 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.052 |
ω scans | θmax = 26.0°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −28→27 |
Tmin = 0.684, Tmax = 1.000 | k = −10→10 |
11932 measured reflections | l = −16→17 |
2766 independent reflections |
Refinement on F2 | 18 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) = 0.089 | w = 1/[σ2(Fo2) + (0.0381P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
2766 reflections | Δρmax = 0.17 e Å−3 |
234 parameters | Δρmin = −0.22 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 | Occ. (<1) | |
N1A | 0.25885 (9) | 0.5771 (2) | 0.68612 (14) | 0.0317 (5) | |
H1A | 0.2759 (10) | 0.581 (3) | 0.7484 (13) | 0.038* | |
C2A | 0.28519 (10) | 0.4980 (3) | 0.62690 (16) | 0.0277 (5) | |
S21A | 0.34844 (3) | 0.40642 (8) | 0.66780 (5) | 0.03738 (19) | |
N3A | 0.25790 (9) | 0.4997 (2) | 0.53269 (14) | 0.0300 (5) | |
H3A | 0.2743 (10) | 0.451 (3) | 0.4920 (16) | 0.036* | |
C4A | 0.20664 (10) | 0.5790 (3) | 0.49381 (17) | 0.0322 (6) | |
O41A | 0.18585 (8) | 0.5684 (2) | 0.40747 (12) | 0.0459 (5) | |
C5A | 0.18328 (10) | 0.6696 (3) | 0.56098 (18) | 0.0333 (6) | |
C51A | 0.12997 (12) | 0.7649 (3) | 0.5241 (2) | 0.0475 (7) | |
H51A | 0.0964 | 0.6976 | 0.5035 | 0.071* | |
H51B | 0.1359 | 0.8266 | 0.4694 | 0.071* | |
H51C | 0.1229 | 0.8324 | 0.5756 | 0.071* | |
C6A | 0.21014 (11) | 0.6632 (3) | 0.65403 (19) | 0.0355 (6) | |
H6A | 0.1947 | 0.7209 | 0.6995 | 0.043* | |
N1B | 0.43409 (8) | 0.0547 (2) | 0.41269 (14) | 0.0295 (5) | |
C2B | 0.42413 (10) | 0.1408 (3) | 0.48397 (17) | 0.0292 (5) | |
N21B | 0.45901 (10) | 0.1257 (3) | 0.57079 (15) | 0.0400 (6) | |
H21B | 0.4895 (9) | 0.064 (3) | 0.572 (2) | 0.048* | |
H22B | 0.4576 (12) | 0.194 (3) | 0.6143 (17) | 0.048* | |
N3B | 0.37991 (9) | 0.2428 (2) | 0.47321 (14) | 0.0324 (5) | |
H3B | 0.3733 (11) | 0.294 (3) | 0.5257 (14) | 0.039* | |
C4B | 0.34171 (10) | 0.2663 (3) | 0.38474 (16) | 0.0302 (6) | |
O41B | 0.30261 (8) | 0.3656 (2) | 0.38063 (12) | 0.0385 (5) | |
C5B | 0.35193 (10) | 0.1756 (3) | 0.31003 (16) | 0.0309 (6) | |
H5B | 0.3281 | 0.1860 | 0.2476 | 0.037* | |
C6B | 0.39636 (11) | 0.0709 (3) | 0.32578 (17) | 0.0322 (6) | |
N61B | 0.40561 (10) | −0.0223 (3) | 0.25604 (15) | 0.0401 (6) | |
H61B | 0.3840 (12) | −0.015 (3) | 0.1984 (15) | 0.048* | |
H62B | 0.4301 (11) | −0.100 (3) | 0.267 (2) | 0.048* | |
O21X | 0.5000 | 0.2981 (3) | 0.7500 | 0.0380 (6) | |
C32X | 0.5000 | 0.7079 (5) | 0.7500 | 0.107 (2) | |
H4XA | 0.5034 | 0.7774 | 0.8050 | 0.160* | 0.5 |
H4XB | 0.4640 | 0.7299 | 0.7033 | 0.160* | 0.5 |
H4XC | 0.5333 | 0.7222 | 0.7194 | 0.160* | 0.5 |
C1X | 0.5132 (11) | 0.4808 (18) | 0.6257 (9) | 0.057 (5) | 0.5 |
H1XA | 0.4750 | 0.5012 | 0.5846 | 0.085* | 0.5 |
H1XB | 0.5322 | 0.3974 | 0.5980 | 0.085* | 0.5 |
H1XC | 0.5372 | 0.5731 | 0.6302 | 0.085* | 0.5 |
C2X | 0.5056 (3) | 0.4358 (5) | 0.7253 (3) | 0.0324 (14) | 0.5 |
N3X | 0.4989 (2) | 0.5475 (5) | 0.7837 (3) | 0.0361 (11) | 0.5 |
C31X | 0.4789 (9) | 0.5120 (18) | 0.8719 (8) | 0.047 (3) | 0.5 |
H3XA | 0.4365 | 0.5203 | 0.8598 | 0.071* | 0.5 |
H3XB | 0.4962 | 0.5842 | 0.9225 | 0.071* | 0.5 |
H3XC | 0.4906 | 0.4077 | 0.8925 | 0.071* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0310 (11) | 0.0408 (12) | 0.0228 (10) | −0.0043 (9) | 0.0042 (8) | −0.0043 (9) |
C2A | 0.0302 (13) | 0.0296 (12) | 0.0227 (12) | −0.0061 (10) | 0.0041 (10) | 0.0004 (10) |
S21A | 0.0345 (3) | 0.0492 (4) | 0.0260 (3) | 0.0068 (3) | 0.0007 (3) | 0.0040 (3) |
N3A | 0.0302 (11) | 0.0369 (12) | 0.0224 (11) | 0.0011 (9) | 0.0041 (9) | −0.0027 (9) |
C4A | 0.0275 (12) | 0.0351 (13) | 0.0319 (14) | −0.0064 (11) | 0.0012 (10) | 0.0055 (11) |
O41A | 0.0419 (11) | 0.0617 (12) | 0.0285 (10) | 0.0030 (9) | −0.0056 (8) | 0.0015 (9) |
C5A | 0.0278 (13) | 0.0327 (13) | 0.0399 (15) | −0.0044 (10) | 0.0080 (11) | 0.0038 (11) |
C51A | 0.0370 (15) | 0.0464 (16) | 0.0598 (19) | 0.0057 (12) | 0.0115 (14) | 0.0094 (14) |
C6A | 0.0336 (14) | 0.0367 (14) | 0.0382 (15) | −0.0041 (11) | 0.0118 (12) | −0.0069 (11) |
N1B | 0.0317 (11) | 0.0320 (11) | 0.0226 (10) | −0.0003 (8) | 0.0008 (8) | −0.0015 (8) |
C2B | 0.0332 (13) | 0.0301 (13) | 0.0230 (12) | −0.0026 (10) | 0.0031 (10) | 0.0022 (10) |
N21B | 0.0448 (13) | 0.0503 (14) | 0.0216 (11) | 0.0123 (11) | −0.0007 (10) | −0.0055 (9) |
N3B | 0.0379 (12) | 0.0368 (12) | 0.0221 (10) | 0.0032 (9) | 0.0055 (9) | −0.0033 (9) |
C4B | 0.0338 (13) | 0.0345 (13) | 0.0213 (12) | −0.0027 (11) | 0.0036 (10) | 0.0031 (10) |
O41B | 0.0403 (10) | 0.0467 (11) | 0.0277 (9) | 0.0137 (8) | 0.0052 (8) | 0.0034 (7) |
C5B | 0.0351 (13) | 0.0355 (13) | 0.0190 (12) | 0.0012 (11) | −0.0016 (10) | −0.0023 (10) |
C6B | 0.0368 (13) | 0.0336 (13) | 0.0245 (13) | −0.0041 (11) | 0.0028 (11) | −0.0011 (11) |
N61B | 0.0451 (14) | 0.0450 (13) | 0.0253 (11) | 0.0135 (10) | −0.0039 (10) | −0.0091 (10) |
O21X | 0.0493 (16) | 0.0340 (14) | 0.0287 (13) | 0.000 | 0.0037 (12) | 0.000 |
C32X | 0.176 (7) | 0.034 (3) | 0.147 (6) | 0.000 | 0.118 (5) | 0.000 |
C1X | 0.072 (7) | 0.062 (8) | 0.044 (6) | −0.035 (6) | 0.029 (5) | −0.004 (5) |
C2X | 0.027 (3) | 0.042 (3) | 0.027 (4) | 0.002 (3) | 0.005 (3) | 0.004 (2) |
N3X | 0.043 (3) | 0.034 (2) | 0.035 (3) | −0.001 (2) | 0.015 (3) | −0.0012 (17) |
C31X | 0.068 (8) | 0.045 (5) | 0.035 (5) | 0.019 (6) | 0.024 (4) | 0.008 (3) |
N1A—C2A | 1.337 (3) | N3B—H3B | 0.911 (17) |
N1A—C6A | 1.368 (3) | C4B—O41B | 1.258 (3) |
N1A—H1A | 0.892 (16) | C4B—C5B | 1.385 (3) |
C2A—N3A | 1.358 (3) | C5B—C6B | 1.373 (3) |
C2A—S21A | 1.683 (2) | C5B—H5B | 0.9500 |
N3A—C4A | 1.401 (3) | C6B—N61B | 1.335 (3) |
N3A—H3A | 0.870 (17) | N61B—H61B | 0.871 (17) |
C4A—O41A | 1.225 (3) | N61B—H62B | 0.882 (17) |
C4A—C5A | 1.435 (4) | O21X—C2X | 1.269 (5) |
C5A—C6A | 1.342 (3) | C32X—N3X | 1.484 (5) |
C5A—C51A | 1.506 (3) | C32X—H4XA | 0.9800 |
C51A—H51A | 0.9800 | C32X—H4XB | 0.9800 |
C51A—H51B | 0.9800 | C32X—H4XC | 0.9800 |
C51A—H51C | 0.9800 | C1X—C2X | 1.513 (8) |
C6A—H6A | 0.9500 | C1X—H1XA | 0.9800 |
N1B—C2B | 1.321 (3) | C1X—H1XB | 0.9800 |
N1B—C6B | 1.369 (3) | C1X—H1XC | 0.9800 |
C2B—N21B | 1.338 (3) | C2X—N3X | 1.313 (5) |
C2B—N3B | 1.355 (3) | N3X—C31X | 1.460 (8) |
N21B—H21B | 0.894 (17) | C31X—H3XA | 0.9800 |
N21B—H22B | 0.866 (17) | C31X—H3XB | 0.9800 |
N3B—C4B | 1.399 (3) | C31X—H3XC | 0.9800 |
C2A—N1A—C6A | 122.8 (2) | O41B—C4B—N3B | 118.0 (2) |
C2A—N1A—H1A | 118.1 (17) | C5B—C4B—N3B | 115.0 (2) |
C6A—N1A—H1A | 118.8 (17) | C6B—C5B—C4B | 120.3 (2) |
N1A—C2A—N3A | 115.3 (2) | C6B—C5B—H5B | 119.8 |
N1A—C2A—S21A | 121.45 (17) | C4B—C5B—H5B | 119.8 |
N3A—C2A—S21A | 123.2 (2) | N61B—C6B—N1B | 115.5 (2) |
C2A—N3A—C4A | 125.8 (2) | N61B—C6B—C5B | 121.5 (2) |
C2A—N3A—H3A | 117.8 (17) | N1B—C6B—C5B | 123.0 (2) |
C4A—N3A—H3A | 116.4 (17) | C6B—N61B—H61B | 120 (2) |
O41A—C4A—N3A | 119.2 (2) | C6B—N61B—H62B | 122.2 (18) |
O41A—C4A—C5A | 125.4 (2) | H61B—N61B—H62B | 118 (3) |
N3A—C4A—C5A | 115.4 (2) | N3X—C32X—H4XA | 109.5 |
C6A—C5A—C4A | 117.7 (2) | N3X—C32X—H4XB | 109.5 |
C6A—C5A—C51A | 123.5 (3) | H4XA—C32X—H4XB | 109.5 |
C4A—C5A—C51A | 118.8 (2) | N3X—C32X—H4XC | 109.5 |
C5A—C51A—H51A | 109.5 | H4XA—C32X—H4XC | 109.5 |
C5A—C51A—H51B | 109.5 | H4XB—C32X—H4XC | 109.5 |
H51A—C51A—H51B | 109.5 | C2X—C1X—H1XA | 109.5 |
C5A—C51A—H51C | 109.5 | C2X—C1X—H1XB | 109.5 |
H51A—C51A—H51C | 109.5 | H1XA—C1X—H1XB | 109.5 |
H51B—C51A—H51C | 109.5 | C2X—C1X—H1XC | 109.5 |
C5A—C6A—N1A | 122.7 (3) | H1XA—C1X—H1XC | 109.5 |
C5A—C6A—H6A | 118.6 | H1XB—C1X—H1XC | 109.5 |
N1A—C6A—H6A | 118.6 | O21X—C2X—N3X | 119.8 (4) |
C2B—N1B—C6B | 116.5 (2) | O21X—C2X—C1X | 123.0 (7) |
N1B—C2B—N21B | 118.5 (2) | N3X—C2X—C1X | 116.8 (7) |
N1B—C2B—N3B | 122.9 (2) | C2X—N3X—C31X | 119.1 (7) |
N21B—C2B—N3B | 118.6 (2) | C2X—N3X—C32X | 119.1 (3) |
C2B—N21B—H21B | 114.5 (18) | C31X—N3X—C32X | 120.6 (7) |
C2B—N21B—H22B | 118.8 (18) | N3X—C31X—H3XA | 109.5 |
H21B—N21B—H22B | 123 (3) | N3X—C31X—H3XB | 109.5 |
C2B—N3B—C4B | 122.2 (2) | H3XA—C31X—H3XB | 109.5 |
C2B—N3B—H3B | 119.4 (16) | N3X—C31X—H3XC | 109.5 |
C4B—N3B—H3B | 118.4 (16) | H3XA—C31X—H3XC | 109.5 |
O41B—C4B—C5B | 127.0 (2) | H3XB—C31X—H3XC | 109.5 |
C6A—N1A—C2A—N3A | −4.5 (3) | N1B—C2B—N3B—C4B | −1.0 (4) |
C6A—N1A—C2A—S21A | 174.29 (19) | N21B—C2B—N3B—C4B | 179.6 (2) |
N1A—C2A—N3A—C4A | 1.7 (3) | C2B—N3B—C4B—O41B | −178.5 (2) |
S21A—C2A—N3A—C4A | −177.09 (19) | C2B—N3B—C4B—C5B | 1.2 (3) |
C2A—N3A—C4A—O41A | −178.5 (2) | O41B—C4B—C5B—C6B | −179.6 (3) |
C2A—N3A—C4A—C5A | 2.4 (3) | N3B—C4B—C5B—C6B | 0.8 (3) |
O41A—C4A—C5A—C6A | 177.2 (2) | C2B—N1B—C6B—N61B | −177.0 (2) |
N3A—C4A—C5A—C6A | −3.8 (3) | C2B—N1B—C6B—C5B | 3.3 (4) |
O41A—C4A—C5A—C51A | −2.1 (4) | C4B—C5B—C6B—N61B | 177.1 (3) |
N3A—C4A—C5A—C51A | 176.9 (2) | C4B—C5B—C6B—N1B | −3.1 (4) |
C4A—C5A—C6A—N1A | 1.3 (4) | O21X—C2X—N3X—C31X | −6.5 (12) |
C51A—C5A—C6A—N1A | −179.4 (2) | C1X—C2X—N3X—C31X | 167 (2) |
C2A—N1A—C6A—C5A | 3.2 (4) | O21X—C2X—N3X—C32X | −174.1 (4) |
C6B—N1B—C2B—N21B | 178.2 (2) | C1X—C2X—N3X—C32X | −0.9 (13) |
C6B—N1B—C2B—N3B | −1.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O41Bi | 0.89 (2) | 1.91 (2) | 2.785 (2) | 166 (2) |
N3A—H3A···O41B | 0.87 (2) | 1.99 (2) | 2.845 (3) | 169 (2) |
N21B—H21B···N1Bii | 0.89 (2) | 2.05 (2) | 2.937 (3) | 172 (2) |
N21B—H22B···O21X | 0.87 (2) | 2.18 (2) | 2.942 (2) | 147 (2) |
N3B—H3B···S21A | 0.91 (2) | 2.42 (2) | 3.329 (2) | 173 (2) |
C5B—H5B···O41Aiii | 0.95 | 2.39 | 3.173 (3) | 140 |
N61B—H61B···O41Aiii | 0.87 (2) | 2.11 (2) | 2.927 (3) | 156 (3) |
N61B—H62B···O21Xii | 0.88 (2) | 2.44 (2) | 3.293 (3) | 163 (3) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, −z+1/2. |
3C5H6N2OS·2C3H6N6 | Dx = 1.514 Mg m−3 |
Mr = 678.81 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 19335 reflections |
a = 17.6827 (7) Å | θ = 1.8–26.9° |
c = 16.4925 (9) Å | µ = 0.31 mm−1 |
V = 4466.0 (4) Å3 | T = 173 K |
Z = 6 | Block, colourless |
F(000) = 2124 | 0.48 × 0.34 × 0.29 mm |
STOE IPDS II two-circle diffractometer | 1960 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.056 |
ω scans | θmax = 26.3°, θmin = 1.8° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −22→22 |
Tmin = 0.828, Tmax = 1.000 | k = −21→22 |
12864 measured reflections | l = −20→20 |
2026 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0518P)2 + 3.6735P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max = 0.001 |
S = 1.12 | Δρmax = 0.25 e Å−3 |
2026 reflections | Δρmin = −0.22 e Å−3 |
166 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.0069 (8) |
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 | Occ. (<1) | |
N1A | 0.37482 (8) | 0.44714 (8) | 0.05842 (8) | 0.0298 (3) | |
H1A | 0.3727 (12) | 0.4957 (10) | 0.0599 (11) | 0.036* | |
C2A | 0.44133 (9) | 0.44463 (9) | 0.09504 (8) | 0.0281 (3) | |
S21A | 0.52440 (2) | 0.53347 (2) | 0.13923 (2) | 0.03323 (17) | |
N3A | 0.43706 (8) | 0.36587 (8) | 0.09583 (7) | 0.0301 (3) | |
H3A | 0.4820 (11) | 0.3643 (12) | 0.1173 (11) | 0.036* | |
O41A | 0.36336 (8) | 0.21806 (7) | 0.08003 (8) | 0.0354 (4) | 0.886 (4) |
C4A | 0.36721 (9) | 0.28828 (9) | 0.06634 (9) | 0.0307 (3) | |
H4A | 0.3634 | 0.2334 | 0.0751 | 0.037* | 0.114 (4) |
C5A | 0.30145 (9) | 0.29595 (9) | 0.02209 (9) | 0.0317 (3) | |
C51A | 0.22838 (11) | 0.21703 (10) | −0.01759 (11) | 0.0399 (4) | |
H51A | 0.1920 | 0.1750 | 0.0241 | 0.060* | 0.886 (4) |
H52A | 0.2525 | 0.1900 | −0.0533 | 0.060* | 0.886 (4) |
H53A | 0.1928 | 0.2344 | −0.0496 | 0.060* | 0.886 (4) |
H54A | 0.2366 | 0.1667 | −0.0092 | 0.060* | 0.114 (4) |
H55A | 0.1726 | 0.2049 | 0.0063 | 0.060* | 0.114 (4) |
H56A | 0.2281 | 0.2278 | −0.0758 | 0.060* | 0.114 (4) |
C6A | 0.30761 (9) | 0.37550 (9) | 0.02055 (9) | 0.0301 (3) | |
H6A | 0.2643 | 0.3821 | −0.0075 | 0.036* | 0.886 (4) |
O61A | 0.2517 (6) | 0.3828 (6) | −0.0055 (6) | 0.036 (3) | 0.114 (4) |
N1B | 0.59548 (7) | 0.34630 (7) | 0.14233 (7) | 0.0293 (3) | |
C2B | 0.67898 (9) | 0.41258 (8) | 0.14251 (8) | 0.0286 (3) | |
N21B | 0.69157 (8) | 0.49371 (8) | 0.14360 (9) | 0.0383 (3) | |
H21B | 0.7446 (11) | 0.5374 (11) | 0.1373 (12) | 0.046* | |
H22B | 0.6434 (11) | 0.5000 (13) | 0.1451 (12) | 0.046* | |
N1C | 0.34975 (7) | 0.59797 (7) | 0.06677 (7) | 0.0269 (3) | |
C2C | 0.41382 (8) | 0.68227 (8) | 0.06760 (8) | 0.0261 (3) | |
N21C | 0.49633 (8) | 0.69786 (8) | 0.06915 (8) | 0.0321 (3) | |
H21C | 0.5370 (11) | 0.7495 (10) | 0.0849 (11) | 0.039* | |
H22C | 0.5035 (12) | 0.6525 (11) | 0.0820 (11) | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0264 (6) | 0.0247 (6) | 0.0420 (7) | 0.0156 (5) | 0.0000 (5) | −0.0018 (5) |
C2A | 0.0262 (6) | 0.0262 (6) | 0.0348 (7) | 0.0153 (5) | 0.0040 (5) | −0.0004 (5) |
S21A | 0.0257 (2) | 0.0261 (2) | 0.0506 (3) | 0.01499 (15) | −0.00431 (13) | −0.00618 (13) |
N3A | 0.0292 (6) | 0.0262 (6) | 0.0394 (6) | 0.0171 (5) | −0.0013 (5) | −0.0022 (5) |
O41A | 0.0319 (6) | 0.0246 (6) | 0.0527 (7) | 0.0164 (5) | −0.0033 (5) | −0.0018 (5) |
C4A | 0.0312 (7) | 0.0271 (7) | 0.0367 (7) | 0.0168 (6) | 0.0018 (5) | −0.0023 (5) |
C5A | 0.0285 (7) | 0.0292 (7) | 0.0362 (7) | 0.0135 (6) | 0.0024 (5) | −0.0024 (5) |
C51A | 0.0357 (8) | 0.0319 (8) | 0.0498 (9) | 0.0151 (6) | −0.0052 (6) | −0.0073 (6) |
C6A | 0.0255 (6) | 0.0303 (7) | 0.0363 (7) | 0.0153 (6) | −0.0004 (5) | −0.0012 (5) |
O61A | 0.030 (5) | 0.033 (5) | 0.054 (6) | 0.023 (4) | −0.014 (4) | −0.004 (4) |
N1B | 0.0232 (5) | 0.0227 (6) | 0.0420 (7) | 0.0114 (4) | 0.0009 (4) | 0.0006 (4) |
C2B | 0.0251 (6) | 0.0246 (6) | 0.0367 (7) | 0.0128 (5) | 0.0011 (5) | −0.0007 (5) |
N21B | 0.0237 (6) | 0.0223 (6) | 0.0689 (9) | 0.0114 (5) | 0.0023 (6) | −0.0007 (5) |
N1C | 0.0223 (5) | 0.0221 (5) | 0.0367 (6) | 0.0114 (4) | −0.0006 (4) | −0.0014 (4) |
C2C | 0.0238 (6) | 0.0236 (6) | 0.0306 (6) | 0.0116 (5) | 0.0013 (5) | −0.0004 (5) |
N21C | 0.0214 (6) | 0.0247 (6) | 0.0496 (7) | 0.0111 (5) | 0.0010 (5) | −0.0006 (5) |
N1A—C2A | 1.3425 (18) | C51A—H55A | 0.9800 |
N1A—C6A | 1.3790 (18) | C51A—H56A | 0.9800 |
N1A—H1A | 0.878 (14) | C6A—O61A | 1.144 (8) |
C2A—N3A | 1.3566 (17) | C6A—H6A | 0.9500 |
C2A—S21A | 1.6879 (14) | N1B—C2Bi | 1.3473 (17) |
N3A—C4A | 1.3964 (18) | N1B—C2B | 1.3503 (17) |
N3A—H3A | 0.884 (14) | C2B—N21B | 1.3373 (17) |
O41A—C4A | 1.2299 (18) | C2B—N1Bii | 1.3473 (17) |
C4A—C5A | 1.436 (2) | N21B—H21B | 0.873 (15) |
C4A—H4A | 0.9500 | N21B—H22B | 0.913 (15) |
C5A—C6A | 1.356 (2) | N1C—C2Ciii | 1.3455 (17) |
C5A—C51A | 1.497 (2) | N1C—C2C | 1.3480 (17) |
C51A—H51A | 0.9800 | C2C—N21C | 1.3427 (17) |
C51A—H52A | 0.9800 | C2C—N1Civ | 1.3455 (17) |
C51A—H53A | 0.9800 | N21C—H21C | 0.873 (15) |
C51A—H54A | 0.9800 | N21C—H22C | 0.898 (15) |
C2A—N1A—C6A | 122.70 (12) | C5A—C51A—H55A | 109.5 |
C2A—N1A—H1A | 119.0 (12) | H54A—C51A—H55A | 109.5 |
C6A—N1A—H1A | 118.2 (12) | C5A—C51A—H56A | 109.5 |
N1A—C2A—N3A | 115.99 (12) | H54A—C51A—H56A | 109.5 |
N1A—C2A—S21A | 122.18 (10) | H55A—C51A—H56A | 109.5 |
N3A—C2A—S21A | 121.81 (11) | O61A—C6A—C5A | 120.0 (5) |
C2A—N3A—C4A | 124.98 (12) | O61A—C6A—N1A | 117.6 (5) |
C2A—N3A—H3A | 116.6 (12) | C5A—C6A—N1A | 122.00 (13) |
C4A—N3A—H3A | 118.5 (12) | C5A—C6A—H6A | 119.0 |
O41A—C4A—N3A | 120.23 (13) | N1A—C6A—H6A | 119.0 |
O41A—C4A—C5A | 123.37 (13) | C2Bi—N1B—C2B | 113.99 (12) |
N3A—C4A—C5A | 116.39 (12) | N21B—C2B—N1Bii | 116.96 (12) |
N3A—C4A—H4A | 121.8 | N21B—C2B—N1B | 117.02 (12) |
C5A—C4A—H4A | 121.8 | N1Bii—C2B—N1B | 126.01 (12) |
C6A—C5A—C4A | 117.32 (13) | C2B—N21B—H21B | 118.4 (13) |
C6A—C5A—C51A | 122.88 (13) | C2B—N21B—H22B | 117.8 (13) |
C4A—C5A—C51A | 119.77 (13) | H21B—N21B—H22B | 123.4 (18) |
C5A—C51A—H51A | 109.5 | C2Ciii—N1C—C2C | 114.42 (12) |
C5A—C51A—H52A | 109.5 | N21C—C2C—N1Civ | 117.48 (12) |
H51A—C51A—H52A | 109.5 | N21C—C2C—N1C | 116.96 (12) |
C5A—C51A—H53A | 109.5 | N1Civ—C2C—N1C | 125.56 (12) |
H51A—C51A—H53A | 109.5 | C2C—N21C—H21C | 117.6 (12) |
H52A—C51A—H53A | 109.5 | C2C—N21C—H22C | 116.5 (12) |
C5A—C51A—H54A | 109.5 | H21C—N21C—H22C | 116.9 (17) |
C6A—N1A—C2A—N3A | −2.7 (2) | C4A—C5A—C6A—O61A | −170.8 (6) |
C6A—N1A—C2A—S21A | 178.52 (11) | C51A—C5A—C6A—O61A | 7.2 (7) |
N1A—C2A—N3A—C4A | −4.1 (2) | C4A—C5A—C6A—N1A | 1.2 (2) |
S21A—C2A—N3A—C4A | 174.65 (11) | C51A—C5A—C6A—N1A | 179.11 (14) |
C2A—N3A—C4A—O41A | −169.51 (14) | C2A—N1A—C6A—O61A | 176.2 (6) |
C2A—N3A—C4A—C5A | 9.1 (2) | C2A—N1A—C6A—C5A | 4.1 (2) |
O41A—C4A—C5A—C6A | 171.39 (14) | C2Bi—N1B—C2B—N21B | −179.01 (9) |
N3A—C4A—C5A—C6A | −7.16 (19) | C2Bi—N1B—C2B—N1Bii | 0.4 (3) |
O41A—C4A—C5A—C51A | −6.6 (2) | C2Ciii—N1C—C2C—N21C | 178.17 (8) |
N3A—C4A—C5A—C51A | 174.82 (13) | C2Ciii—N1C—C2C—N1Civ | −2.0 (3) |
Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iii) −x+y, −x+1, z; (iv) −y+1, x−y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···N1C | 0.88 (1) | 2.05 (2) | 2.9173 (16) | 172 (2) |
N3A—H3A···N1B | 0.88 (1) | 2.22 (2) | 3.0861 (16) | 166 (2) |
C4A—H4A···O61Av | 0.95 | 2.31 | 3.093 (8) | 140 |
C6A—H6A···O41Avi | 0.95 | 2.30 | 3.2278 (18) | 167 |
N21B—H21B···O41Aii | 0.87 (2) | 2.09 (2) | 2.9184 (17) | 159 (2) |
N21B—H22B···S21A | 0.91 (2) | 2.46 (2) | 3.3640 (13) | 173 (2) |
N21C—H21C···S21Avii | 0.87 (2) | 2.72 (2) | 3.5085 (13) | 152 (2) |
N21C—H21C···O61Aiv | 0.87 (2) | 2.39 (2) | 2.960 (9) | 124 (2) |
N21C—H22C···S21A | 0.90 (2) | 2.50 (2) | 3.3875 (13) | 172 (2) |
Symmetry codes: (ii) −x+y+1, −x+1, z; (iv) −y+1, x−y+1, z; (v) y, −x+y, −z; (vi) x−y, x, −z; (vii) x−y+2/3, x+1/3, −z+1/3. |
5MTU is 5-methyl-2-thiouracil (2-thiothymine), DAPY is 2,4-diaminopyrimidine, DMSO is dimethyl sulfoxide, DMF is N,N-dimethylformamide, DAPT is 2,4-diamino-6-phenyl-1,3,5-triazine, AICT is 6-amino-3H-isocytosine, DMAC is N,N-dimethylacetamide and MELA is melamine (2,4,6-triamino-1,3,5-triazine). |
Crystal | Compound (1) (mg, mmol) | Coformer (mg, mmol) | Solvent (µl) | Temperature (K) |
(I) | 5MTU (2.5, 0.018) | DAPY (4.0, 0.036) | DMSO (50) | 323 |
(II) | 5MTU (2.4, 0.017) | DAPY (1.8, 0.016) | DMF (44) | 323 |
(III) | 5MTU (2.0, 0.014) | DAPT (2.0, 0.011) | DMF (55) | 295 |
(IV) | 5MTU (2.3, 0.016) | AICT (3.8, 0.030) | DMF (230) | 323 |
(V) | 5MTU (2.3, 0.016) | AICT (2.0, 0.016) | DMAC (190) | 323 |
(VI) | 5MTU (2.2, 0.015) | MELA (4.0, 0.032) | DMSO (166) | 323 |
The table contains the components of each crystal (including the solvent if incorporated in the crystal structure), the type of synthon formed between the target compound and the respective coformer, and the type of hydrogen-bond network formed in the crystal structure. |
Crystal | Target Compound | Coformer | Solvent | Synthon | Hydrogen-bond network |
(I) | 5MTU | DAPY | - | 2dN·O;N·N | 3d |
(IV) | 5MTU | AICT | DMF | 2dN·S;N·O | 3d |
(V) | 5MTU | AICT | DMAC | 2dN·S;N·O | 3d |
(II) | 5MTU | DAPY | DMF | 3sN·S;N·N;N·O | 2d |
(III) | 5MTU | DAPT | DMF | 3sN·S;N·N;N·O | 2d |
(VI) | 5MTU | MELA | - | 3sN·S;N·N;N·O | 2d |
YOZVEQ | 6MTU | DAPY | NMP | 2dN·O;N·N | 1d |
YOZVIU | 6MTU | DAPY | - | 3sN·S;N·N;N·O | 1d |
YOZVOA | 6MTU | DAPY | DMAC | 3sN·S;N·N;N·O | 1d |
YOZVUG | 6MTU | DAPY | DMF | 3sN·S;N·N;N·O | 1d |
YOZWAN | 6MTU | TAPY | DMF | 3sN·S;N·N;N·O | 1d |
YOZWER | 6MTU | AICT | DMF | 3sN·S;N·N;N·O | 1d |
YOZWIV | 6MTU | AICT | DMSO | 3sN·S;N·N;N·O | 1d |
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