Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102021960/bm1512sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102021960/bm1512Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102021960/bm1512IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102021960/bm1512IIIsup4.hkl |
CCDC references: 204056; 204057; 204058
All compounds were obtained from Key Organics Ltd and crystals were grown from ethanol solution.
All H atoms were included in the refinement, at calculated positions, as riding models, with C—H set to 0.95 (Ar—H) and 0.98 Å (CH3), and N—H set to 0.88 Å, except for the water H atoms, which were located in difference syntheses and for which both positional and displacement parameters were refined. For (I), the number of Friedel pairs is 548. A high Rint value of 0.111 for (III) results from the weak high-angle data.
For all compounds, data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
C5H4ClN5 | Dx = 1.663 Mg m−3 |
Mr = 169.58 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41212 | Cell parameters from 8615 reflections |
a = 7.0855 (10) Å | θ = 2.9–27.5° |
c = 26.990 (5) Å | µ = 0.49 mm−1 |
V = 1355.0 (4) Å3 | T = 150 K |
Z = 8 | Rectangular prism, colourless |
F(000) = 688 | 0.15 × 0.08 × 0.07 mm |
Bruker–Nonius KappaCCD area-detector diffractometer | 1535 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 1151 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −5→9 |
Tmin = 0.910, Tmax = 0.964 | l = −24→34 |
4943 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0335P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1535 reflections | Δρmax = 0.26 e Å−3 |
100 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 548 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (10) |
C5H4ClN5 | Z = 8 |
Mr = 169.58 | Mo Kα radiation |
Tetragonal, P41212 | µ = 0.49 mm−1 |
a = 7.0855 (10) Å | T = 150 K |
c = 26.990 (5) Å | 0.15 × 0.08 × 0.07 mm |
V = 1355.0 (4) Å3 |
Bruker–Nonius KappaCCD area-detector diffractometer | 1535 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1151 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.964 | Rint = 0.065 |
4943 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.083 | Δρmax = 0.26 e Å−3 |
S = 1.04 | Δρmin = −0.31 e Å−3 |
1535 reflections | Absolute structure: Flack (1983), 548 Friedel pairs |
100 parameters | Absolute structure parameter: 0.00 (10) |
0 restraints |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4911 (3) | 0.6115 (3) | 0.09891 (7) | 0.0187 (5) | |
C2 | 0.3717 (3) | 0.4593 (4) | 0.09459 (8) | 0.0181 (6) | |
N21 | 0.2115 (3) | 0.4681 (3) | 0.12083 (7) | 0.0261 (6) | |
H21 | 0.1297 | 0.3748 | 0.1194 | 0.033* | |
H22 | 0.1881 | 0.5672 | 0.1395 | 0.033* | |
N3 | 0.4012 (3) | 0.3036 (3) | 0.06637 (7) | 0.0180 (5) | |
C4 | 0.5651 (3) | 0.3104 (4) | 0.04214 (8) | 0.0159 (6) | |
C5 | 0.6988 (4) | 0.4549 (3) | 0.04394 (8) | 0.0155 (6) | |
C6 | 0.6494 (3) | 0.6054 (4) | 0.07369 (8) | 0.0157 (6) | |
Cl6 | 0.79634 (9) | 0.79992 (9) | 0.07836 (2) | 0.02353 (18) | |
N7 | 0.8518 (3) | 0.4129 (3) | 0.01381 (7) | 0.0195 (5) | |
C8 | 0.8073 (3) | 0.2481 (3) | −0.00486 (9) | 0.0216 (6) | |
H8 | 0.8869 | 0.1817 | −0.0272 | 0.027* | |
N9 | 0.6365 (3) | 0.1797 (3) | 0.01049 (6) | 0.0182 (5) | |
H9 | 0.5835 | 0.0725 | 0.0016 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0191 (12) | 0.0158 (12) | 0.0211 (11) | 0.0017 (10) | −0.0005 (9) | 0.0008 (10) |
C2 | 0.0174 (14) | 0.0160 (14) | 0.0209 (13) | 0.0018 (12) | 0.0041 (12) | 0.0038 (12) |
N21 | 0.0235 (12) | 0.0151 (11) | 0.0398 (13) | −0.0027 (11) | 0.0119 (13) | −0.0061 (11) |
N3 | 0.0186 (12) | 0.0149 (11) | 0.0205 (10) | 0.0010 (10) | 0.0022 (9) | −0.0026 (10) |
C4 | 0.0180 (14) | 0.0135 (14) | 0.0161 (12) | −0.0005 (13) | −0.0027 (11) | −0.0022 (12) |
C5 | 0.0165 (13) | 0.0163 (13) | 0.0139 (12) | 0.0017 (13) | −0.0013 (13) | 0.0016 (11) |
C6 | 0.0162 (14) | 0.0147 (14) | 0.0162 (12) | −0.0011 (11) | −0.0027 (11) | 0.0034 (11) |
Cl6 | 0.0237 (4) | 0.0184 (4) | 0.0285 (3) | −0.0060 (3) | 0.0020 (3) | −0.0042 (3) |
N7 | 0.0194 (12) | 0.0205 (12) | 0.0187 (12) | −0.0003 (9) | 0.0018 (10) | 0.0003 (10) |
C8 | 0.0217 (14) | 0.0234 (15) | 0.0197 (13) | 0.0019 (12) | 0.0039 (13) | −0.0011 (11) |
N9 | 0.0206 (12) | 0.0141 (11) | 0.0200 (12) | −0.0031 (10) | 0.0042 (10) | −0.0044 (10) |
N1—C6 | 1.313 (3) | C4—C5 | 1.396 (3) |
N1—C2 | 1.375 (3) | C5—C6 | 1.380 (3) |
C2—N21 | 1.339 (3) | C5—N7 | 1.388 (3) |
C2—N3 | 1.357 (3) | C6—Cl6 | 1.732 (3) |
N21—H21 | 0.88 | N7—C8 | 1.310 (3) |
N21—H22 | 0.88 | C8—N9 | 1.368 (3) |
N3—C4 | 1.334 (3) | C8—H8 | 0.95 |
C4—N9 | 1.358 (3) | N9—H9 | 0.88 |
C6—N1—C2 | 117.1 (2) | C6—C5—C4 | 114.5 (2) |
N21—C2—N3 | 117.7 (2) | N7—C5—C4 | 110.6 (2) |
N21—C2—N1 | 116.1 (2) | N1—C6—C5 | 122.9 (2) |
N3—C2—N1 | 126.2 (2) | N1—C6—Cl6 | 116.75 (18) |
C2—N21—H21 | 120.0 | C5—C6—Cl6 | 120.31 (19) |
C2—N21—H22 | 120.0 | C8—N7—C5 | 103.2 (2) |
H21—N21—H22 | 120.0 | N7—C8—N9 | 114.3 (2) |
C4—N3—C2 | 112.3 (2) | N7—C8—H8 | 122.8 |
N3—C4—N9 | 127.4 (2) | N9—C8—H8 | 122.8 |
N3—C4—C5 | 126.9 (2) | C4—N9—C8 | 106.17 (19) |
N9—C4—C5 | 105.7 (2) | C4—N9—H9 | 126.9 |
C6—C5—N7 | 134.8 (2) | C8—N9—H9 | 126.9 |
C6—N1—C2—N21 | 179.7 (2) | C2—N1—C6—Cl6 | 178.67 (16) |
C6—N1—C2—N3 | −0.5 (4) | N7—C5—C6—N1 | 179.5 (2) |
N21—C2—N3—C4 | −179.8 (2) | C4—C5—C6—N1 | 1.0 (3) |
N1—C2—N3—C4 | 0.4 (3) | N7—C5—C6—Cl6 | 0.6 (4) |
C2—N3—C4—N9 | −179.1 (2) | C4—C5—C6—Cl6 | −177.89 (18) |
C2—N3—C4—C5 | 0.5 (3) | C6—C5—N7—C8 | −178.5 (3) |
N3—C4—C5—C6 | −1.2 (4) | C4—C5—N7—C8 | 0.0 (3) |
N9—C4—C5—C6 | 178.52 (19) | C5—N7—C8—N9 | 0.4 (3) |
N3—C4—C5—N7 | 180.0 (2) | N3—C4—N9—C8 | −179.8 (2) |
N9—C4—C5—N7 | −0.3 (3) | C5—C4—N9—C8 | 0.5 (3) |
C2—N1—C6—C5 | −0.3 (3) | N7—C8—N9—C4 | −0.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N1i | 0.88 | 2.22 | 3.019 (3) | 150 |
N21—H22···N3ii | 0.88 | 2.15 | 3.027 (3) | 174 |
N9—H9···N7iii | 0.88 | 2.02 | 2.888 (3) | 168 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/4; (ii) −x+1/2, y+1/2, −z+1/4; (iii) y, x−1, −z. |
C11H8ClN5S·0.5H2O | F(000) = 2352 |
Mr = 286.74 | Dx = 1.556 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.353 (3) Å | Cell parameters from 11629 reflections |
b = 7.743 (2) Å | θ = 2.9–27.5° |
c = 47.60 (1) Å | µ = 0.48 mm−1 |
β = 95.85 (3)° | T = 120 K |
V = 4896 (2) Å3 | Plate, colourless |
Z = 16 | 0.20 × 0.16 × 0.05 mm |
Bruker–Nonius KappaCCD area-detector diffractometer | 3842 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 3045 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 3.1° |
ϕ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −9→9 |
Tmin = 0.737, Tmax = 0.982 | l = −56→56 |
10871 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3 |
3842 reflections | (Δ/σ)max < 0.001 |
342 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
C11H8ClN5S·0.5H2O | V = 4896 (2) Å3 |
Mr = 286.74 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.353 (3) Å | µ = 0.48 mm−1 |
b = 7.743 (2) Å | T = 120 K |
c = 47.60 (1) Å | 0.20 × 0.16 × 0.05 mm |
β = 95.85 (3)° |
Bruker–Nonius KappaCCD area-detector diffractometer | 3842 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 3045 reflections with I > 2σ(I) |
Tmin = 0.737, Tmax = 0.982 | Rint = 0.060 |
10871 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.47 e Å−3 |
3842 reflections | Δρmin = −0.57 e Å−3 |
342 parameters |
Geometry. Mean plane data ex SHELXL97 for molecule (II) ############################################# Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) − 7.2128 (0.0109) x + 6.3182 (0.0051) y + 12.3729 (0.0406) z = 4.8904 (0.0125) * −0.0080 (0.0014) N1A * 0.0158 (0.0015) C2A * −0.0057 (0.0014) N3A * −0.0107 (0.0015) C4A * 0.0169 (0.0016) C5A * −0.0082 (0.0015) C6A Rms deviation of fitted atoms = 0.0117 7.3492 (0.0116) x + 6.1911 (0.0057) y − 14.0546 (0.0466) z = 1.6649 (0.0105) Angle to previous plane (with approximate e.s.d.) = 72.21 (0.06) * 0.0028 (0.0017) C61A * 0.0027 (0.0018) C62A * −0.0058 (0.0018) C63A * 0.0034 (0.0017) C64A * 0.0022 (0.0017) C65A * −0.0053 (0.0017) C66A Rms deviation of fitted atoms = 0.0040 6.5943 (0.0111) x + 0.3491 (0.0077) y − 43.5118 (0.0287) z = 0.5136 (0.0079) Angle to previous plane (with approximate e.s.d.) = 58.89 (0.09) * 0.0105 (0.0015) N1B * −0.0237 (0.0016) C2B * 0.0089 (0.0015) N3B * 0.0170 (0.0016) C4B * −0.0273 (0.0017) C5B * 0.0147 (0.0016) C6B Rms deviation of fitted atoms = 0.0183 5.9714 (0.0120) x + 6.8892 (0.0049) y + 2.1861 (0.0471) z = 1.5122 (0.0037) Angle to previous plane (with approximate e.s.d.) = 79.57 (0.08) * 0.0026 (0.0016) C61B * 0.0017 (0.0017) C62B * −0.0034 (0.0017) C63B * 0.0008 (0.0017) C64B * 0.0036 (0.0017) C65B * −0.0053 (0.0017) C66B Rms deviation of fitted atoms = 0.0032 |
x | y | z | Uiso*/Ueq | ||
N1A | 0.11719 (14) | 0.3707 (2) | 0.27365 (4) | 0.0144 (5) | |
C2A | 0.07470 (18) | 0.2850 (3) | 0.29454 (5) | 0.0146 (5) | |
N21A | −0.01316 (14) | 0.2067 (2) | 0.28637 (4) | 0.0193 (5) | |
H21A | −0.0445 | 0.1484 | 0.2987 | 0.024* | |
H22A | −0.0394 | 0.2138 | 0.2687 | 0.024* | |
N3A | 0.11255 (14) | 0.2713 (2) | 0.32189 (4) | 0.0143 (5) | |
C4A | 0.19913 (17) | 0.3582 (3) | 0.32754 (5) | 0.0138 (5) | |
C5A | 0.24720 (18) | 0.4550 (3) | 0.30837 (5) | 0.0137 (5) | |
C6A | 0.20279 (18) | 0.4547 (3) | 0.28061 (5) | 0.0147 (5) | |
N7A | 0.33602 (14) | 0.5279 (2) | 0.32141 (4) | 0.0177 (5) | |
C8A | 0.33918 (18) | 0.4728 (3) | 0.34752 (5) | 0.0175 (6) | |
H8A | 0.3924 | 0.5002 | 0.3616 | 0.022* | |
N9A | 0.25868 (14) | 0.3718 (2) | 0.35263 (4) | 0.0157 (5) | |
H9A | 0.2475 | 0.3249 | 0.3689 | 0.020* | |
S6A | 0.26779 (5) | 0.56315 (9) | 0.255617 (13) | 0.0240 (2) | |
C61A | 0.18479 (19) | 0.5587 (3) | 0.22408 (5) | 0.0191 (6) | |
C62A | 0.0977 (2) | 0.6560 (4) | 0.22137 (6) | 0.0258 (7) | |
H62A | 0.0777 | 0.7166 | 0.2372 | 0.032* | |
C63A | 0.0391 (2) | 0.6656 (4) | 0.19560 (6) | 0.0269 (7) | |
H63A | −0.0214 | 0.7311 | 0.1936 | 0.034* | |
C64A | 0.0710 (2) | 0.5776 (3) | 0.17283 (5) | 0.0222 (6) | |
Cl6A | 0.00034 (5) | 0.59529 (9) | 0.139897 (15) | 0.0340 (2) | |
C65A | 0.1571 (2) | 0.4801 (3) | 0.17500 (5) | 0.0246 (6) | |
H65A | 0.1772 | 0.4206 | 0.1590 | 0.031* | |
C66A | 0.2140 (2) | 0.4701 (3) | 0.20089 (5) | 0.0225 (6) | |
H66A | 0.2735 | 0.4021 | 0.2028 | 0.028* | |
N1B | 0.52614 (15) | 0.1031 (2) | 0.06852 (4) | 0.0155 (5) | |
C2B | 0.59473 (19) | 0.2186 (3) | 0.08063 (5) | 0.0159 (6) | |
N21B | 0.56467 (16) | 0.3853 (2) | 0.07955 (4) | 0.0220 (5) | |
H21B | 0.6049 | 0.4665 | 0.0871 | 0.027* | |
H22B | 0.5049 | 0.4127 | 0.0713 | 0.027* | |
N3B | 0.68703 (15) | 0.1850 (2) | 0.09360 (4) | 0.0160 (5) | |
C4B | 0.70584 (18) | 0.0145 (3) | 0.09489 (5) | 0.0165 (6) | |
C5B | 0.64082 (19) | −0.1162 (3) | 0.08501 (5) | 0.0170 (6) | |
C6B | 0.54950 (18) | −0.0639 (3) | 0.07062 (5) | 0.0155 (6) | |
N7B | 0.68496 (16) | −0.2783 (2) | 0.09055 (5) | 0.0224 (5) | |
C8B | 0.7737 (2) | −0.2395 (3) | 0.10299 (6) | 0.0285 (7) | |
H8B | 0.8222 | −0.3247 | 0.1092 | 0.036* | |
N9B | 0.79129 (16) | −0.0658 (2) | 0.10637 (5) | 0.0230 (5) | |
H9B | 0.8464 | −0.0164 | 0.1143 | 0.029* | |
S6B | 0.46857 (5) | −0.22657 (8) | 0.055773 (15) | 0.02315 (19) | |
C61B | 0.37448 (18) | −0.1154 (3) | 0.03378 (5) | 0.0183 (6) | |
C62B | 0.38038 (19) | −0.1115 (3) | 0.00479 (6) | 0.0225 (6) | |
H62B | 0.4376 | −0.1582 | −0.0028 | 0.028* | |
C63B | 0.3026 (2) | −0.0392 (3) | −0.01301 (6) | 0.0234 (6) | |
H63B | 0.3059 | −0.0366 | −0.0329 | 0.029* | |
C64B | 0.22071 (18) | 0.0288 (3) | −0.00147 (5) | 0.0205 (6) | |
Cl6B | 0.12372 (5) | 0.12240 (8) | −0.023529 (15) | 0.0320 (2) | |
C65B | 0.21377 (19) | 0.0261 (3) | 0.02730 (5) | 0.0214 (6) | |
H65B | 0.1568 | 0.0742 | 0.0349 | 0.027* | |
C66B | 0.29051 (19) | −0.0473 (3) | 0.04489 (5) | 0.0205 (6) | |
H66B | 0.2861 | −0.0514 | 0.0647 | 0.026* | |
O1W | 0.44835 (14) | 0.6389 (3) | 0.12886 (5) | 0.0242 (5) | |
H1W | 0.461 (2) | 0.725 (4) | 0.1192 (7) | 0.051 (11)* | |
H2W | 0.433 (3) | 0.685 (4) | 0.1441 (8) | 0.063 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0128 (11) | 0.0174 (11) | 0.0126 (11) | −0.0008 (9) | −0.0002 (9) | 0.0013 (9) |
C2A | 0.0135 (13) | 0.0176 (13) | 0.0126 (13) | 0.0017 (11) | 0.0005 (11) | −0.0018 (10) |
N21A | 0.0184 (12) | 0.0303 (12) | 0.0085 (11) | −0.0108 (10) | −0.0019 (9) | 0.0007 (9) |
N3A | 0.0152 (11) | 0.0182 (11) | 0.0090 (11) | −0.0006 (9) | −0.0013 (9) | 0.0030 (8) |
C4A | 0.0132 (13) | 0.0163 (13) | 0.0111 (13) | 0.0023 (11) | −0.0022 (11) | −0.0014 (10) |
C5A | 0.0143 (13) | 0.0154 (13) | 0.0108 (13) | −0.0017 (10) | −0.0021 (11) | 0.0011 (10) |
C6A | 0.0164 (14) | 0.0161 (13) | 0.0113 (13) | −0.0001 (11) | −0.0006 (11) | 0.0012 (10) |
N7A | 0.0170 (12) | 0.0237 (12) | 0.0113 (11) | −0.0057 (10) | −0.0043 (9) | −0.0004 (9) |
C8A | 0.0163 (14) | 0.0207 (14) | 0.0144 (14) | −0.0005 (11) | −0.0039 (11) | −0.0012 (10) |
N9A | 0.0189 (12) | 0.0191 (11) | 0.0079 (11) | −0.0042 (9) | −0.0041 (9) | 0.0036 (8) |
S6A | 0.0218 (4) | 0.0387 (4) | 0.0101 (3) | −0.0132 (3) | −0.0048 (3) | 0.0070 (3) |
C61A | 0.0194 (15) | 0.0258 (14) | 0.0107 (14) | −0.0115 (12) | −0.0047 (11) | 0.0051 (10) |
C62A | 0.0243 (16) | 0.0357 (16) | 0.0167 (15) | −0.0072 (13) | −0.0014 (12) | −0.0010 (12) |
C63A | 0.0183 (15) | 0.0351 (16) | 0.0263 (17) | −0.0014 (13) | −0.0022 (13) | 0.0075 (13) |
C64A | 0.0241 (16) | 0.0285 (15) | 0.0123 (14) | −0.0105 (13) | −0.0068 (12) | 0.0075 (11) |
Cl6A | 0.0325 (4) | 0.0505 (5) | 0.0162 (4) | −0.0095 (3) | −0.0114 (3) | 0.0109 (3) |
C65A | 0.0298 (16) | 0.0299 (15) | 0.0134 (14) | −0.0035 (13) | −0.0018 (12) | 0.0008 (11) |
C66A | 0.0236 (15) | 0.0274 (15) | 0.0155 (14) | −0.0040 (12) | −0.0039 (12) | 0.0055 (11) |
N1B | 0.0181 (12) | 0.0135 (11) | 0.0139 (12) | 0.0035 (9) | −0.0036 (9) | −0.0011 (8) |
C2B | 0.0229 (15) | 0.0161 (13) | 0.0081 (13) | −0.0017 (11) | −0.0016 (11) | −0.0017 (10) |
N21B | 0.0249 (13) | 0.0151 (11) | 0.0233 (13) | 0.0017 (10) | −0.0108 (10) | −0.0025 (9) |
N3B | 0.0198 (12) | 0.0152 (11) | 0.0119 (11) | 0.0031 (9) | −0.0041 (9) | −0.0002 (8) |
C4B | 0.0201 (15) | 0.0199 (14) | 0.0084 (13) | 0.0017 (12) | −0.0037 (11) | −0.0015 (10) |
C5B | 0.0226 (15) | 0.0169 (13) | 0.0107 (13) | 0.0023 (12) | −0.0024 (11) | −0.0022 (10) |
C6B | 0.0179 (14) | 0.0197 (14) | 0.0086 (13) | −0.0008 (11) | −0.0006 (11) | −0.0017 (10) |
N7B | 0.0252 (13) | 0.0167 (11) | 0.0228 (13) | 0.0058 (10) | −0.0089 (10) | −0.0011 (9) |
C8B | 0.0289 (17) | 0.0214 (15) | 0.0313 (17) | 0.0068 (13) | −0.0159 (14) | −0.0044 (12) |
N9B | 0.0211 (12) | 0.0207 (12) | 0.0244 (13) | 0.0021 (10) | −0.0109 (10) | −0.0051 (9) |
S6B | 0.0237 (4) | 0.0150 (3) | 0.0280 (4) | −0.0002 (3) | −0.0110 (3) | −0.0002 (3) |
C61B | 0.0195 (14) | 0.0144 (13) | 0.0192 (14) | −0.0030 (11) | −0.0060 (12) | −0.0006 (10) |
C62B | 0.0215 (15) | 0.0221 (14) | 0.0240 (16) | −0.0009 (12) | 0.0024 (13) | −0.0051 (11) |
C63B | 0.0323 (17) | 0.0242 (15) | 0.0126 (14) | −0.0052 (13) | −0.0029 (12) | −0.0009 (11) |
C64B | 0.0210 (15) | 0.0152 (14) | 0.0231 (15) | −0.0018 (12) | −0.0085 (12) | 0.0010 (11) |
Cl6B | 0.0354 (4) | 0.0274 (4) | 0.0283 (4) | 0.0020 (3) | −0.0201 (3) | 0.0012 (3) |
C65B | 0.0196 (15) | 0.0237 (14) | 0.0203 (15) | 0.0037 (12) | −0.0006 (12) | −0.0018 (11) |
C66B | 0.0271 (16) | 0.0187 (14) | 0.0149 (14) | 0.0004 (12) | −0.0010 (12) | 0.0002 (10) |
O1W | 0.0244 (11) | 0.0330 (12) | 0.0147 (11) | 0.0008 (9) | −0.0011 (9) | −0.0041 (10) |
N1A—C6A | 1.328 (3) | N1B—C2B | 1.365 (3) |
N1A—C2A | 1.366 (3) | C2B—N3B | 1.346 (3) |
C2A—N21A | 1.342 (3) | C2B—N21B | 1.351 (3) |
C2A—N3A | 1.352 (3) | N21B—H21B | 0.88 |
N21A—H21A | 0.88 | N21B—H22B | 0.88 |
N21A—H22A | 0.88 | N3B—C4B | 1.345 (3) |
N3A—C4A | 1.341 (3) | C4B—N9B | 1.364 (3) |
C4A—N9A | 1.370 (3) | C4B—C5B | 1.384 (3) |
C4A—C5A | 1.388 (3) | C5B—C6B | 1.396 (3) |
C5A—C6A | 1.392 (3) | C5B—N7B | 1.400 (3) |
C5A—N7A | 1.400 (3) | C6B—S6B | 1.760 (2) |
C6A—S6A | 1.756 (2) | N7B—C8B | 1.304 (3) |
N7A—C8A | 1.311 (3) | C8B—N9B | 1.372 (3) |
C8A—N9A | 1.371 (3) | C8B—H8B | 0.95 |
C8A—H8A | 0.95 | N9B—H9B | 0.88 |
N9A—H9A | 0.88 | S6B—C61B | 1.774 (3) |
S6A—C61A | 1.773 (3) | C61B—C62B | 1.390 (4) |
C61A—C62A | 1.381 (4) | C61B—C66B | 1.391 (3) |
C61A—C66A | 1.389 (4) | C62B—C63B | 1.390 (3) |
C62A—C63A | 1.388 (4) | C62B—H62B | 0.95 |
C62A—H62A | 0.95 | C63B—C64B | 1.377 (3) |
C63A—C64A | 1.384 (4) | C63B—H63B | 0.95 |
C63A—H63A | 0.95 | C64B—C65B | 1.382 (3) |
C64A—C65A | 1.370 (4) | C64B—Cl6B | 1.740 (3) |
C64A—Cl6A | 1.751 (3) | C65B—C66B | 1.378 (3) |
C65A—C66A | 1.383 (3) | C65B—H65B | 0.95 |
C65A—H65A | 0.95 | C66B—H66B | 0.95 |
C66A—H66A | 0.95 | O1W—H1W | 0.84 (4) |
N1B—C6B | 1.332 (3) | O1W—H2W | 0.85 (4) |
C6A—N1A—C2A | 117.8 (2) | N3B—C2B—N21B | 117.2 (2) |
N21A—C2A—N3A | 118.3 (2) | N3B—C2B—N1B | 127.6 (2) |
N21A—C2A—N1A | 115.1 (2) | N21B—C2B—N1B | 115.2 (2) |
N3A—C2A—N1A | 126.7 (2) | C2B—N21B—H21B | 120.0 |
C2A—N21A—H21A | 120.0 | C2B—N21B—H22B | 120.0 |
C2A—N21A—H22A | 120.0 | H21B—N21B—H22B | 120.0 |
H21A—N21A—H22A | 120.0 | C4B—N3B—C2B | 111.64 (19) |
C4A—N3A—C2A | 112.6 (2) | N3B—C4B—N9B | 127.7 (2) |
N3A—C4A—N9A | 128.7 (2) | N3B—C4B—C5B | 126.5 (2) |
N3A—C4A—C5A | 125.9 (2) | N9B—C4B—C5B | 105.9 (2) |
N9A—C4A—C5A | 105.4 (2) | C4B—C5B—C6B | 116.2 (2) |
C4A—C5A—C6A | 116.3 (2) | C4B—C5B—N7B | 110.7 (2) |
C4A—C5A—N7A | 110.7 (2) | C6B—C5B—N7B | 133.0 (2) |
C6A—C5A—N7A | 132.9 (2) | N1B—C6B—C5B | 120.3 (2) |
N1A—C6A—C5A | 120.7 (2) | N1B—C6B—S6B | 122.37 (18) |
N1A—C6A—S6A | 122.53 (18) | C5B—C6B—S6B | 117.32 (18) |
C5A—C6A—S6A | 116.75 (18) | C8B—N7B—C5B | 103.0 (2) |
C8A—N7A—C5A | 103.48 (19) | N7B—C8B—N9B | 114.6 (2) |
N7A—C8A—N9A | 113.8 (2) | N7B—C8B—H8B | 122.7 |
N7A—C8A—H8A | 123.1 | N9B—C8B—H8B | 122.7 |
N9A—C8A—H8A | 123.1 | C4B—N9B—C8B | 105.9 (2) |
C4A—N9A—C8A | 106.56 (19) | C4B—N9B—H9B | 127.1 |
C4A—N9A—H9A | 126.7 | C8B—N9B—H9B | 127.1 |
C8A—N9A—H9A | 126.7 | C6B—S6B—C61B | 104.99 (11) |
C6A—S6A—C61A | 104.76 (11) | C62B—C61B—C66B | 119.9 (2) |
C62A—C61A—C66A | 119.8 (2) | C62B—C61B—S6B | 119.21 (19) |
C62A—C61A—S6A | 121.1 (2) | C66B—C61B—S6B | 120.6 (2) |
C66A—C61A—S6A | 118.7 (2) | C63B—C62B—C61B | 120.0 (2) |
C61A—C62A—C63A | 120.4 (3) | C63B—C62B—H62B | 120.0 |
C61A—C62A—H62A | 119.8 | C61B—C62B—H62B | 120.0 |
C63A—C62A—H62A | 119.8 | C64B—C63B—C62B | 119.0 (2) |
C64A—C63A—C62A | 118.4 (3) | C64B—C63B—H63B | 120.5 |
C64A—C63A—H63A | 120.8 | C62B—C63B—H63B | 120.5 |
C62A—C63A—H63A | 120.8 | C63B—C64B—C65B | 121.7 (2) |
C65A—C64A—C63A | 122.4 (2) | C63B—C64B—Cl6B | 119.4 (2) |
C65A—C64A—Cl6A | 118.8 (2) | C65B—C64B—Cl6B | 118.9 (2) |
C63A—C64A—Cl6A | 118.8 (2) | C66B—C65B—C64B | 119.2 (2) |
C64A—C65A—C66A | 118.6 (3) | C66B—C65B—H65B | 120.4 |
C64A—C65A—H65A | 120.7 | C64B—C65B—H65B | 120.4 |
C66A—C65A—H65A | 120.7 | C65B—C66B—C61B | 120.3 (2) |
C65A—C66A—C61A | 120.5 (3) | C65B—C66B—H66B | 119.9 |
C65A—C66A—H66A | 119.7 | C61B—C66B—H66B | 119.9 |
C61A—C66A—H66A | 119.7 | H1W—O1W—H2W | 102 (3) |
C6B—N1B—C2B | 117.6 (2) | ||
C6A—N1A—C2A—N21A | 178.16 (19) | C6B—N1B—C2B—N3B | 3.4 (4) |
C6A—N1A—C2A—N3A | −2.4 (3) | C6B—N1B—C2B—N21B | −175.8 (2) |
N21A—C2A—N3A—C4A | −178.5 (2) | N21B—C2B—N3B—C4B | 176.1 (2) |
N1A—C2A—N3A—C4A | 2.1 (3) | N1B—C2B—N3B—C4B | −3.1 (3) |
C2A—N3A—C4A—N9A | −179.3 (2) | C2B—N3B—C4B—N9B | 179.7 (2) |
C2A—N3A—C4A—C5A | 0.7 (3) | C2B—N3B—C4B—C5B | −1.2 (3) |
N3A—C4A—C5A—C6A | −2.8 (3) | N3B—C4B—C5B—C6B | 4.6 (4) |
N9A—C4A—C5A—C6A | 177.2 (2) | N9B—C4B—C5B—C6B | −176.1 (2) |
N3A—C4A—C5A—N7A | −179.8 (2) | N3B—C4B—C5B—N7B | −178.6 (2) |
N9A—C4A—C5A—N7A | 0.1 (3) | N9B—C4B—C5B—N7B | 0.7 (3) |
C2A—N1A—C6A—C5A | −0.1 (3) | C2B—N1B—C6B—C5B | 0.6 (3) |
C2A—N1A—C6A—S6A | 177.53 (17) | C2B—N1B—C6B—S6B | −179.50 (17) |
C4A—C5A—C6A—N1A | 2.4 (3) | C4B—C5B—C6B—N1B | −4.1 (3) |
N7A—C5A—C6A—N1A | 178.6 (2) | N7B—C5B—C6B—N1B | −180.0 (2) |
C4A—C5A—C6A—S6A | −175.34 (17) | C4B—C5B—C6B—S6B | 175.96 (18) |
N7A—C5A—C6A—S6A | 0.9 (4) | N7B—C5B—C6B—S6B | 0.1 (4) |
C4A—C5A—N7A—C8A | 0.5 (3) | C4B—C5B—N7B—C8B | −0.8 (3) |
C6A—C5A—N7A—C8A | −175.9 (3) | C6B—C5B—N7B—C8B | 175.2 (3) |
C5A—N7A—C8A—N9A | −0.9 (3) | C5B—N7B—C8B—N9B | 0.6 (3) |
N3A—C4A—N9A—C8A | 179.3 (2) | N3B—C4B—N9B—C8B | 179.0 (2) |
C5A—C4A—N9A—C8A | −0.7 (2) | C5B—C4B—N9B—C8B | −0.3 (3) |
N7A—C8A—N9A—C4A | 1.0 (3) | N7B—C8B—N9B—C4B | −0.3 (3) |
N1A—C6A—S6A—C61A | 8.8 (2) | N1B—C6B—S6B—C61B | 11.2 (2) |
C5A—C6A—S6A—C61A | −173.52 (19) | C5B—C6B—S6B—C61B | −168.85 (19) |
C6A—S6A—C61A—C62A | 70.4 (2) | C6B—S6B—C61B—C62B | 101.1 (2) |
C6A—S6A—C61A—C66A | −116.5 (2) | C6B—S6B—C61B—C66B | −85.2 (2) |
C66A—C61A—C62A—C63A | 0.0 (4) | C66B—C61B—C62B—C63B | 0.2 (4) |
S6A—C61A—C62A—C63A | 173.1 (2) | S6B—C61B—C62B—C63B | 173.98 (18) |
C61A—C62A—C63A—C64A | −0.8 (4) | C61B—C62B—C63B—C64B | 0.4 (4) |
C62A—C63A—C64A—C65A | 0.9 (4) | C62B—C63B—C64B—C65B | −0.3 (4) |
C62A—C63A—C64A—Cl6A | −177.61 (19) | C62B—C63B—C64B—Cl6B | 179.09 (18) |
C63A—C64A—C65A—C66A | −0.2 (4) | C63B—C64B—C65B—C66B | −0.3 (4) |
Cl6A—C64A—C65A—C66A | 178.36 (19) | Cl6B—C64B—C65B—C66B | −179.76 (18) |
C64A—C65A—C66A—C61A | −0.7 (4) | C64B—C65B—C66B—C61B | 0.9 (4) |
C62A—C61A—C66A—C65A | 0.8 (4) | C62B—C61B—C66B—C65B | −0.8 (4) |
S6A—C61A—C66A—C65A | −172.45 (19) | S6B—C61B—C66B—C65B | −174.56 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N7Ai | 0.88 | 2.22 | 3.072 (3) | 163 |
N21A—H22A···N1Aii | 0.88 | 2.49 | 3.300 (3) | 154 |
N21A—H22A···S6Ai | 0.88 | 2.84 | 3.326 (2) | 117 |
N9A—H9A···N3Biii | 0.88 | 2.19 | 2.965 (3) | 146 |
N21B—H21B···N7Biv | 0.88 | 2.25 | 3.077 (3) | 158 |
N21B—H22B···Cl6Bv | 0.88 | 2.72 | 3.475 (2) | 145 |
N21B—H22B···S6Biv | 0.88 | 2.92 | 3.415 (2) | 118 |
N9B—H9B···O1Wvi | 0.88 | 1.89 | 2.757 (3) | 166 |
O1W—H1W···S6Biv | 0.84 (4) | 3.05 (4) | 3.668 (2) | 132 (3) |
O1W—H2W···N3Avii | 0.85 (4) | 1.91 (4) | 2.756 (3) | 174 (3) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x, y, −z+1/2; (iii) −x+1, y, −z+1/2; (iv) x, y+1, z; (v) −x+1/2, −y+1/2, −z; (vi) x+1/2, y−1/2, z; (vii) −x+1/2, y+1/2, −z+1/2. |
C12H11N5S·0.333H2O | Z = 6 |
Mr = 263.32 | F(000) = 824 |
Triclinic, P1 | Dx = 1.389 Mg m−3 |
a = 10.8074 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6355 (3) Å | Cell parameters from 40289 reflections |
c = 15.3922 (3) Å | θ = 2.9–27.5° |
α = 85.468 (2)° | µ = 0.25 mm−1 |
β = 83.265 (1)° | T = 150 K |
γ = 79.7992 (9)° | Plate, colourless |
V = 1888.46 (7) Å3 | 0.12 × 0.12 × 0.01 mm |
Bruker–Nonius KappaCCD area detector diffractometer | 8568 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 4357 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.111 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −15→15 |
Tmin = 0.931, Tmax = 0.998 | l = −19→19 |
36016 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0537P)2] where P = (Fo2 + 2Fc2)/3 |
8568 reflections | (Δ/σ)max < 0.001 |
507 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C12H11N5S·0.333H2O | γ = 79.7992 (9)° |
Mr = 263.32 | V = 1888.46 (7) Å3 |
Triclinic, P1 | Z = 6 |
a = 10.8074 (2) Å | Mo Kα radiation |
b = 11.6355 (3) Å | µ = 0.25 mm−1 |
c = 15.3922 (3) Å | T = 150 K |
α = 85.468 (2)° | 0.12 × 0.12 × 0.01 mm |
β = 83.265 (1)° |
Bruker–Nonius KappaCCD area detector diffractometer | 8568 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 4357 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.998 | Rint = 0.111 |
36016 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.28 e Å−3 |
8568 reflections | Δρmin = −0.30 e Å−3 |
507 parameters |
Geometry. Mean plane data ex SHELXL97 for molecule (III) ############################################## 10.4927 (0.0026) x + 4.6335 (0.0105) y + 2.9885 (0.0160) z = 6.7844 (0.0093) * 0.0052 (0.0017) N1A * −0.0075 (0.0018) C2A * 0.0048 (0.0017) N3A * −0.0014 (0.0018) C4A * −0.0004 (0.0018) C5A * −0.0007 (0.0018) C6A Rms deviation of fitted atoms = 0.0043 − 5.4722 (0.0101) x + 7.4941 (0.0096) y + 6.3778 (0.0145) z = 6.0185 (0.0099) Angle to previous plane (with approximate e.s.d.) = 73.08 (0.07) * 0.0062 (0.0018) C61A * −0.0105 (0.0018) C62A * 0.0045 (0.0019) C63A * 0.0061 (0.0020) C64A * −0.0107 (0.0019) C65A * 0.0044 (0.0019) C66A Rms deviation of fitted atoms = 0.0075 6.0317 (0.0082) x − 6.9901 (0.0085) y − 6.1715 (0.0143) z = 0.8298 (0.0063) Angle to previous plane (with approximate e.s.d.) = 3.58 (0.17) * −0.0083 (0.0016) N1B * 0.0115 (0.0017) C2B * 0.0013 (0.0016) N3B * −0.0164 (0.0017) C4B * 0.0180 (0.0017) C5B * −0.0061 (0.0017) C6B Rms deviation of fitted atoms = 0.0118 7.2341 (0.0091) x + 4.8210 (0.0120) y − 8.8851 (0.0140) z = 1.7212 (0.0017) Angle to previous plane (with approximate e.s.d.) = 63.21 (0.08) * 0.0129 (0.0019) C61B * 0.0009 (0.0019) C62B * −0.0136 (0.0020) C63B * 0.0124 (0.0020) C64B * 0.0014 (0.0021) C65B * −0.0140 (0.0020) C66B Rms deviation of fitted atoms = 0.0109 − 3.3624 (0.0097) x + 8.8480 (0.0067) y + 7.2945 (0.0131) z = 4.4083 (0.0057) Angle to previous plane (with approximate e.s.d.) = 74.01 (0.08) * −0.0312 (0.0016) N1C * 0.0498 (0.0016) C2C * −0.0161 (0.0016) N3C * −0.0317 (0.0016) C4C * 0.0449 (0.0017) C5C * −0.0157 (0.0017) C6C Rms deviation of fitted atoms = 0.0341 9.4416 (0.0076) x + 7.3141 (0.0126) y + 3.0886 (0.0192) z = 3.3833 (0.0088) Angle to previous plane (with approximate e.s.d.) = 80.80 (0.08) * −0.0007 (0.0021) C61C * −0.0085 (0.0024) C62C * 0.0135 (0.0025) C63C * −0.0092 (0.0022) C64C * 0.0001 (0.0023) C65C * 0.0048 (0.0023) C66C Rms deviation of fitted atoms = 0.0078 |
x | y | z | Uiso*/Ueq | ||
N1A | 0.3642 (2) | 0.30213 (19) | 0.52465 (12) | 0.0301 (5) | |
C2A | 0.4158 (3) | 0.1868 (2) | 0.51806 (16) | 0.0309 (7) | |
N21A | 0.4572 (2) | 0.1529 (2) | 0.43641 (13) | 0.0461 (7) | |
H21A | 0.4942 | 0.0802 | 0.4285 | 0.058* | |
H22A | 0.4472 | 0.2034 | 0.3911 | 0.058* | |
N3A | 0.4344 (2) | 0.10474 (18) | 0.58421 (12) | 0.0297 (5) | |
C4A | 0.3377 (2) | 0.2620 (2) | 0.67783 (15) | 0.0270 (6) | |
C5A | 0.3924 (2) | 0.1484 (2) | 0.66205 (15) | 0.0268 (6) | |
C6A | 0.3248 (2) | 0.3389 (2) | 0.60420 (15) | 0.0278 (6) | |
N7A | 0.3079 (2) | 0.2750 (2) | 0.76790 (13) | 0.0341 (6) | |
C8A | 0.3435 (3) | 0.1697 (2) | 0.80220 (16) | 0.0351 (7) | |
H8A | 0.3343 | 0.1507 | 0.8635 | 0.044* | |
N9A | 0.3949 (2) | 0.08953 (19) | 0.74260 (12) | 0.0317 (6) | |
H9A | 0.4239 | 0.0149 | 0.7536 | 0.040* | |
S6A | 0.25434 (8) | 0.48439 (7) | 0.62075 (4) | 0.0422 (2) | |
C61A | 0.2540 (3) | 0.5521 (2) | 0.51377 (16) | 0.0309 (7) | |
C62A | 0.1672 (3) | 0.5339 (2) | 0.45815 (18) | 0.0372 (7) | |
H62A | 0.1135 | 0.4778 | 0.4746 | 0.046* | |
C63A | 0.1601 (3) | 0.5983 (3) | 0.37874 (18) | 0.0429 (8) | |
H63A | 0.0996 | 0.5871 | 0.3415 | 0.054* | |
C64A | 0.2397 (3) | 0.6788 (3) | 0.35270 (18) | 0.0437 (8) | |
C65A | 0.3269 (3) | 0.6929 (3) | 0.40822 (18) | 0.0435 (8) | |
H65A | 0.3836 | 0.7462 | 0.3908 | 0.054* | |
C66A | 0.3332 (3) | 0.6317 (2) | 0.48803 (17) | 0.0381 (7) | |
H66A | 0.3926 | 0.6443 | 0.5256 | 0.048* | |
C67A | 0.2325 (4) | 0.7479 (3) | 0.26553 (19) | 0.0715 (12) | |
H67A | 0.3154 | 0.7347 | 0.2311 | 0.089* | |
H68A | 0.2076 | 0.8314 | 0.2754 | 0.089* | |
H69A | 0.1698 | 0.7226 | 0.2336 | 0.089* | |
N1B | 0.4174 (2) | 0.23536 (19) | 0.00824 (13) | 0.0304 (5) | |
C2B | 0.4887 (2) | 0.3190 (2) | −0.02002 (16) | 0.0283 (6) | |
N21B | 0.4712 (2) | 0.3682 (2) | −0.10040 (13) | 0.0369 (6) | |
H21B | 0.5148 | 0.4225 | −0.1229 | 0.046* | |
H22B | 0.4161 | 0.3462 | −0.1306 | 0.046* | |
N3B | 0.57405 (19) | 0.35560 (19) | 0.02360 (12) | 0.0284 (5) | |
C4B | 0.5849 (2) | 0.2979 (2) | 0.10239 (15) | 0.0285 (6) | |
C5B | 0.5216 (3) | 0.2087 (2) | 0.13611 (15) | 0.0294 (6) | |
C6B | 0.4335 (2) | 0.1803 (2) | 0.08603 (16) | 0.0297 (6) | |
N7B | 0.5603 (2) | 0.16558 (19) | 0.21780 (13) | 0.0332 (6) | |
C8B | 0.6418 (3) | 0.2321 (2) | 0.23028 (16) | 0.0355 (7) | |
H8B | 0.6838 | 0.2245 | 0.2818 | 0.044* | |
N9B | 0.6616 (2) | 0.31325 (19) | 0.16328 (12) | 0.0305 (5) | |
H9B | 0.7131 | 0.3646 | 0.1601 | 0.038* | |
S6B | 0.34445 (8) | 0.07289 (7) | 0.12837 (4) | 0.0439 (2) | |
C61B | 0.2487 (3) | 0.0670 (3) | 0.04367 (17) | 0.0353 (7) | |
C62B | 0.2625 (3) | −0.0346 (2) | 0.00110 (17) | 0.0373 (7) | |
H62B | 0.3244 | −0.0996 | 0.0161 | 0.047* | |
C63B | 0.1858 (3) | −0.0423 (3) | −0.06389 (18) | 0.0410 (8) | |
H63B | 0.1946 | −0.1135 | −0.0922 | 0.051* | |
C64B | 0.0972 (3) | 0.0517 (3) | −0.08792 (18) | 0.0429 (8) | |
C65B | 0.0832 (3) | 0.1529 (3) | −0.0431 (2) | 0.0471 (8) | |
H65B | 0.0217 | 0.2182 | −0.0582 | 0.059* | |
C66B | 0.1569 (3) | 0.1607 (3) | 0.02277 (18) | 0.0446 (8) | |
H66B | 0.1446 | 0.2300 | 0.0537 | 0.056* | |
C67B | 0.0196 (3) | 0.0451 (3) | −0.1620 (2) | 0.0620 (10) | |
H67B | 0.0525 | 0.0885 | −0.2142 | 0.077* | |
H68B | −0.0686 | 0.0795 | −0.1451 | 0.077* | |
H69B | 0.0246 | −0.0368 | −0.1747 | 0.077* | |
N1C | 0.2602 (2) | 0.34012 (19) | 0.30746 (12) | 0.0284 (5) | |
C2C | 0.3496 (2) | 0.4063 (2) | 0.27944 (15) | 0.0264 (6) | |
N21C | 0.43612 (19) | 0.40878 (18) | 0.33629 (12) | 0.0297 (5) | |
H21C | 0.4976 | 0.4494 | 0.3218 | 0.037* | |
H22C | 0.4306 | 0.3698 | 0.3876 | 0.037* | |
N3C | 0.36326 (19) | 0.46780 (18) | 0.20215 (12) | 0.0262 (5) | |
C5C | 0.1614 (2) | 0.4151 (2) | 0.18142 (15) | 0.0274 (6) | |
C4C | 0.2662 (2) | 0.4675 (2) | 0.15567 (15) | 0.0263 (6) | |
C6C | 0.1647 (2) | 0.3452 (2) | 0.25935 (16) | 0.0287 (6) | |
N7C | 0.0755 (2) | 0.4395 (2) | 0.11866 (13) | 0.0332 (6) | |
C8C | 0.1322 (3) | 0.5028 (2) | 0.05819 (16) | 0.0334 (7) | |
H8C | 0.0961 | 0.5328 | 0.0059 | 0.042* | |
N9C | 0.2469 (2) | 0.52242 (19) | 0.07558 (12) | 0.0311 (5) | |
H9C | 0.2981 | 0.5624 | 0.0421 | 0.039* | |
S6C | 0.04176 (7) | 0.26601 (7) | 0.29177 (5) | 0.0411 (2) | |
C61C | 0.0948 (2) | 0.1781 (2) | 0.38371 (16) | 0.0308 (7) | |
C62C | 0.1771 (3) | 0.0754 (3) | 0.37279 (19) | 0.0527 (9) | |
H62C | 0.2107 | 0.0533 | 0.3155 | 0.066* | |
C63C | 0.2113 (3) | 0.0040 (3) | 0.4445 (2) | 0.0592 (10) | |
H63C | 0.2712 | −0.0655 | 0.4361 | 0.074* | |
C64C | 0.1609 (3) | 0.0305 (3) | 0.52823 (17) | 0.0373 (7) | |
C65C | 0.0791 (3) | 0.1331 (3) | 0.53829 (18) | 0.0503 (9) | |
H65C | 0.0444 | 0.1543 | 0.5956 | 0.063* | |
C66C | 0.0454 (3) | 0.2074 (3) | 0.46688 (17) | 0.0488 (9) | |
H66C | −0.0118 | 0.2786 | 0.4755 | 0.061* | |
C67C | 0.1958 (3) | −0.0524 (3) | 0.60574 (19) | 0.0558 (9) | |
H67C | 0.2844 | −0.0900 | 0.5952 | 0.070* | |
H68C | 0.1414 | −0.1123 | 0.6135 | 0.070* | |
H69C | 0.1842 | −0.0086 | 0.6588 | 0.070* | |
O1W | 0.8062 (2) | 0.4882 (2) | 0.15590 (13) | 0.0392 (5) | |
H1W | 0.781 (3) | 0.553 (3) | 0.180 (2) | 0.071 (13)* | |
H2W | 0.887 (4) | 0.474 (3) | 0.149 (2) | 0.079 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0435 (14) | 0.0225 (14) | 0.0236 (11) | −0.0053 (11) | −0.0034 (10) | 0.0011 (10) |
C2A | 0.0438 (18) | 0.0223 (17) | 0.0262 (14) | −0.0073 (13) | −0.0020 (12) | 0.0029 (12) |
N21A | 0.086 (2) | 0.0225 (14) | 0.0237 (12) | 0.0000 (13) | 0.0018 (12) | 0.0019 (10) |
N3A | 0.0431 (14) | 0.0227 (13) | 0.0226 (11) | −0.0076 (11) | 0.0000 (10) | 0.0017 (10) |
C4A | 0.0353 (16) | 0.0219 (16) | 0.0239 (14) | −0.0084 (13) | 0.0006 (11) | −0.0003 (12) |
C5A | 0.0346 (16) | 0.0245 (16) | 0.0218 (13) | −0.0085 (13) | −0.0038 (11) | 0.0041 (12) |
C6A | 0.0353 (16) | 0.0230 (16) | 0.0257 (14) | −0.0076 (13) | −0.0025 (11) | 0.0009 (12) |
N7A | 0.0473 (15) | 0.0296 (15) | 0.0247 (12) | −0.0088 (12) | 0.0003 (10) | 0.0008 (11) |
C8A | 0.0481 (19) | 0.0345 (19) | 0.0225 (14) | −0.0101 (15) | 0.0011 (12) | 0.0003 (13) |
N9A | 0.0510 (15) | 0.0213 (13) | 0.0225 (11) | −0.0068 (11) | −0.0043 (10) | 0.0027 (10) |
S6A | 0.0659 (6) | 0.0264 (4) | 0.0287 (4) | 0.0017 (4) | 0.0025 (3) | −0.0001 (3) |
C61A | 0.0371 (17) | 0.0199 (16) | 0.0327 (15) | 0.0023 (13) | −0.0031 (13) | −0.0008 (12) |
C62A | 0.0351 (17) | 0.0298 (18) | 0.0446 (17) | −0.0005 (14) | 0.0008 (13) | −0.0080 (14) |
C63A | 0.0455 (19) | 0.040 (2) | 0.0401 (17) | 0.0119 (16) | −0.0132 (14) | −0.0122 (15) |
C64A | 0.065 (2) | 0.0263 (18) | 0.0324 (16) | 0.0109 (17) | −0.0040 (15) | 0.0017 (14) |
C65A | 0.054 (2) | 0.0304 (19) | 0.0443 (18) | −0.0075 (15) | −0.0010 (15) | 0.0063 (15) |
C66A | 0.0437 (19) | 0.0303 (18) | 0.0394 (16) | −0.0030 (15) | −0.0099 (14) | 0.0033 (14) |
C67A | 0.107 (3) | 0.049 (2) | 0.0431 (19) | 0.021 (2) | −0.0062 (19) | 0.0089 (17) |
N1B | 0.0396 (14) | 0.0244 (14) | 0.0274 (12) | −0.0097 (11) | −0.0010 (10) | 0.0026 (10) |
C2B | 0.0323 (16) | 0.0240 (16) | 0.0269 (14) | −0.0027 (13) | −0.0020 (12) | 0.0030 (12) |
N21B | 0.0465 (15) | 0.0390 (15) | 0.0298 (12) | −0.0201 (12) | −0.0111 (11) | 0.0088 (11) |
N3B | 0.0341 (13) | 0.0271 (13) | 0.0233 (11) | −0.0061 (11) | −0.0025 (10) | 0.0038 (10) |
C4B | 0.0364 (16) | 0.0230 (16) | 0.0238 (14) | 0.0007 (13) | −0.0017 (12) | −0.0026 (12) |
C5B | 0.0416 (17) | 0.0219 (16) | 0.0216 (13) | −0.0020 (13) | 0.0029 (12) | 0.0011 (12) |
C6B | 0.0385 (17) | 0.0228 (16) | 0.0257 (14) | −0.0044 (13) | 0.0032 (12) | 0.0002 (12) |
N7B | 0.0503 (16) | 0.0256 (14) | 0.0221 (12) | −0.0045 (12) | −0.0032 (10) | 0.0036 (10) |
C8B | 0.0499 (19) | 0.0283 (18) | 0.0242 (14) | 0.0016 (15) | −0.0038 (13) | 0.0053 (13) |
N9B | 0.0386 (14) | 0.0271 (14) | 0.0251 (11) | −0.0062 (11) | −0.0030 (10) | 0.0033 (10) |
S6B | 0.0622 (6) | 0.0410 (5) | 0.0315 (4) | −0.0236 (4) | −0.0011 (3) | 0.0074 (3) |
C61B | 0.0367 (17) | 0.0308 (18) | 0.0377 (16) | −0.0122 (14) | 0.0062 (13) | 0.0019 (14) |
C62B | 0.0404 (18) | 0.0295 (18) | 0.0387 (16) | −0.0038 (14) | 0.0051 (13) | −0.0007 (14) |
C63B | 0.0453 (19) | 0.038 (2) | 0.0396 (17) | −0.0125 (16) | 0.0064 (14) | −0.0080 (14) |
C64B | 0.0399 (19) | 0.048 (2) | 0.0394 (17) | −0.0126 (16) | 0.0054 (14) | 0.0049 (15) |
C65B | 0.0410 (19) | 0.038 (2) | 0.056 (2) | 0.0024 (16) | 0.0024 (15) | 0.0023 (16) |
C66B | 0.053 (2) | 0.0325 (19) | 0.0460 (18) | −0.0101 (16) | 0.0108 (15) | −0.0060 (15) |
C67B | 0.056 (2) | 0.078 (3) | 0.051 (2) | −0.016 (2) | −0.0030 (17) | 0.0049 (19) |
N1C | 0.0351 (14) | 0.0254 (13) | 0.0247 (11) | −0.0066 (11) | −0.0028 (10) | 0.0022 (10) |
C2C | 0.0309 (16) | 0.0192 (15) | 0.0270 (14) | −0.0003 (13) | −0.0022 (12) | 0.0008 (12) |
N21C | 0.0326 (13) | 0.0303 (14) | 0.0265 (11) | −0.0077 (11) | −0.0075 (10) | 0.0079 (10) |
N3C | 0.0312 (13) | 0.0232 (13) | 0.0228 (11) | −0.0020 (10) | −0.0036 (10) | 0.0029 (10) |
C5C | 0.0342 (16) | 0.0275 (16) | 0.0197 (13) | −0.0030 (13) | −0.0033 (11) | −0.0012 (12) |
C4C | 0.0327 (16) | 0.0232 (16) | 0.0209 (13) | −0.0017 (13) | −0.0001 (12) | 0.0001 (11) |
C6C | 0.0375 (17) | 0.0226 (16) | 0.0258 (14) | −0.0076 (13) | 0.0011 (12) | −0.0019 (12) |
N7C | 0.0390 (14) | 0.0375 (15) | 0.0241 (11) | −0.0112 (12) | −0.0053 (10) | 0.0057 (11) |
C8C | 0.0387 (18) | 0.0364 (18) | 0.0261 (14) | −0.0074 (14) | −0.0090 (13) | 0.0018 (13) |
N9C | 0.0356 (14) | 0.0353 (15) | 0.0222 (11) | −0.0093 (11) | −0.0037 (10) | 0.0070 (10) |
S6C | 0.0444 (5) | 0.0433 (5) | 0.0381 (4) | −0.0179 (4) | −0.0102 (3) | 0.0137 (4) |
C61C | 0.0340 (16) | 0.0266 (17) | 0.0329 (15) | −0.0116 (13) | −0.0028 (12) | 0.0055 (12) |
C62C | 0.072 (2) | 0.043 (2) | 0.0335 (17) | 0.0039 (18) | 0.0099 (16) | 0.0017 (15) |
C63C | 0.074 (3) | 0.039 (2) | 0.051 (2) | 0.0117 (18) | 0.0066 (18) | 0.0092 (17) |
C64C | 0.0374 (17) | 0.0355 (19) | 0.0402 (17) | −0.0116 (15) | −0.0080 (13) | 0.0096 (14) |
C65C | 0.063 (2) | 0.057 (2) | 0.0252 (15) | 0.0006 (19) | 0.0022 (14) | 0.0005 (15) |
C66C | 0.060 (2) | 0.041 (2) | 0.0366 (17) | 0.0110 (17) | −0.0014 (15) | −0.0030 (15) |
C67C | 0.063 (2) | 0.055 (2) | 0.0517 (19) | −0.0209 (18) | −0.0159 (17) | 0.0226 (17) |
O1W | 0.0384 (14) | 0.0433 (15) | 0.0370 (12) | −0.0081 (11) | −0.0034 (10) | −0.0074 (11) |
N1A—C6A | 1.326 (3) | C61B—C62B | 1.374 (4) |
N1A—C2A | 1.366 (3) | C61B—C66B | 1.383 (4) |
C2A—N3A | 1.347 (3) | C62B—C63B | 1.389 (4) |
C2A—N21A | 1.349 (3) | C62B—H62B | 0.95 |
N21A—H21A | 0.88 | C63B—C64B | 1.378 (4) |
N21A—H22A | 0.88 | C63B—H63B | 0.95 |
N3A—C5A | 1.337 (3) | C64B—C65B | 1.388 (4) |
C4A—C5A | 1.377 (3) | C64B—C67B | 1.506 (4) |
C4A—C6A | 1.392 (3) | C65B—C66B | 1.378 (4) |
C4A—N7A | 1.400 (3) | C65B—H65B | 0.95 |
C5A—N9A | 1.369 (3) | C66B—H66B | 0.95 |
C6A—S6A | 1.754 (3) | C67B—H67B | 0.98 |
N7A—C8A | 1.306 (3) | C67B—H68B | 0.98 |
C8A—N9A | 1.361 (3) | C67B—H69B | 0.98 |
C8A—H8A | 0.95 | N1C—C6C | 1.330 (3) |
N9A—H9A | 0.88 | N1C—C2C | 1.351 (3) |
S6A—C61A | 1.769 (3) | C2C—N3C | 1.345 (3) |
C61A—C66A | 1.375 (4) | C2C—N21C | 1.359 (3) |
C61A—C62A | 1.394 (4) | N21C—H21C | 0.88 |
C62A—C63A | 1.385 (4) | N21C—H22C | 0.88 |
C62A—H62A | 0.95 | N3C—C4C | 1.338 (3) |
C63A—C64A | 1.387 (4) | C5C—C4C | 1.383 (4) |
C63A—H63A | 0.95 | C5C—C6C | 1.395 (3) |
C64A—C65A | 1.382 (4) | C5C—N7C | 1.396 (3) |
C64A—C67A | 1.512 (4) | C4C—N9C | 1.364 (3) |
C65A—C66A | 1.373 (4) | C6C—S6C | 1.752 (3) |
C65A—H65A | 0.95 | N7C—C8C | 1.304 (3) |
C66A—H66A | 0.95 | C8C—N9C | 1.359 (3) |
C67A—H67A | 0.98 | C8C—H8C | 0.95 |
C67A—H68A | 0.98 | N9C—H9C | 0.88 |
C67A—H69A | 0.98 | S6C—C61C | 1.770 (3) |
N1B—C6B | 1.328 (3) | C61C—C62C | 1.366 (4) |
N1B—C2B | 1.360 (3) | C61C—C66C | 1.373 (3) |
C2B—N21B | 1.341 (3) | C62C—C63C | 1.374 (4) |
C2B—N3B | 1.346 (3) | C62C—H62C | 0.95 |
N21B—H21B | 0.88 | C63C—C64C | 1.375 (4) |
N21B—H22B | 0.88 | C63C—H63C | 0.95 |
N3B—C4B | 1.346 (3) | C64C—C65C | 1.362 (4) |
C4B—N9B | 1.363 (3) | C64C—C67C | 1.513 (4) |
C4B—C5B | 1.378 (4) | C65C—C66C | 1.386 (4) |
C5B—C6B | 1.391 (4) | C65C—H65C | 0.95 |
C5B—N7B | 1.399 (3) | C66C—H66C | 0.95 |
C6B—S6B | 1.750 (3) | C67C—H67C | 0.98 |
N7B—C8B | 1.310 (3) | C67C—H68C | 0.98 |
C8B—N9B | 1.366 (3) | C67C—H69C | 0.98 |
C8B—H8B | 0.95 | O1W—H1W | 0.85 (4) |
N9B—H9B | 0.88 | O1W—H2W | 0.86 (4) |
S6B—C61B | 1.770 (3) | ||
C6A—N1A—C2A | 117.6 (2) | C62B—C61B—C66B | 119.8 (3) |
N3A—C2A—N21A | 116.7 (2) | C62B—C61B—S6B | 119.0 (2) |
N3A—C2A—N1A | 127.2 (2) | C66B—C61B—S6B | 121.1 (2) |
N21A—C2A—N1A | 116.1 (2) | C61B—C62B—C63B | 120.0 (3) |
C2A—N21A—H21A | 120.0 | C61B—C62B—H62B | 120.0 |
C2A—N21A—H22A | 120.0 | C63B—C62B—H62B | 120.0 |
H21A—N21A—H22A | 120.0 | C64B—C63B—C62B | 120.9 (3) |
C5A—N3A—C2A | 111.6 (2) | C64B—C63B—H63B | 119.5 |
C5A—C4A—C6A | 115.9 (2) | C62B—C63B—H63B | 119.5 |
C5A—C4A—N7A | 110.6 (2) | C63B—C64B—C65B | 118.2 (3) |
C6A—C4A—N7A | 133.5 (2) | C63B—C64B—C67B | 120.7 (3) |
N3A—C5A—N9A | 127.1 (2) | C65B—C64B—C67B | 121.1 (3) |
N3A—C5A—C4A | 127.1 (2) | C66B—C65B—C64B | 121.3 (3) |
N9A—C5A—C4A | 105.7 (2) | C66B—C65B—H65B | 119.3 |
N1A—C6A—C4A | 120.6 (2) | C64B—C65B—H65B | 119.3 |
N1A—C6A—S6A | 121.77 (19) | C65B—C66B—C61B | 119.7 (3) |
C4A—C6A—S6A | 117.64 (19) | C65B—C66B—H66B | 120.2 |
C8A—N7A—C4A | 103.2 (2) | C61B—C66B—H66B | 120.2 |
N7A—C8A—N9A | 114.3 (2) | C64B—C67B—H67B | 109.5 |
N7A—C8A—H8A | 122.9 | C64B—C67B—H68B | 109.5 |
N9A—C8A—H8A | 122.9 | H67B—C67B—H68B | 109.5 |
C8A—N9A—C5A | 106.2 (2) | C64B—C67B—H69B | 109.5 |
C8A—N9A—H9A | 126.9 | H67B—C67B—H69B | 109.5 |
C5A—N9A—H9A | 126.9 | H68B—C67B—H69B | 109.5 |
C6A—S6A—C61A | 104.04 (12) | C6C—N1C—C2C | 117.9 (2) |
C66A—C61A—C62A | 119.5 (3) | N3C—C2C—N1C | 127.6 (2) |
C66A—C61A—S6A | 119.2 (2) | N3C—C2C—N21C | 117.1 (2) |
C62A—C61A—S6A | 121.0 (2) | N1C—C2C—N21C | 115.3 (2) |
C63A—C62A—C61A | 119.5 (3) | C2C—N21C—H21C | 120.0 |
C63A—C62A—H62A | 120.3 | C2C—N21C—H22C | 120.0 |
C61A—C62A—H62A | 120.3 | H21C—N21C—H22C | 120.0 |
C62A—C63A—C64A | 121.1 (3) | C4C—N3C—C2C | 111.3 (2) |
C62A—C63A—H63A | 119.4 | C4C—C5C—C6C | 116.1 (2) |
C64A—C63A—H63A | 119.4 | C4C—C5C—N7C | 110.6 (2) |
C65A—C64A—C63A | 118.1 (3) | C6C—C5C—N7C | 133.2 (3) |
C65A—C64A—C67A | 121.0 (3) | N3C—C4C—N9C | 127.6 (2) |
C63A—C64A—C67A | 120.9 (3) | N3C—C4C—C5C | 126.5 (2) |
C66A—C65A—C64A | 121.5 (3) | N9C—C4C—C5C | 105.8 (2) |
C66A—C65A—H65A | 119.3 | N1C—C6C—C5C | 119.7 (2) |
C64A—C65A—H65A | 119.3 | N1C—C6C—S6C | 121.4 (2) |
C65A—C66A—C61A | 120.3 (3) | C5C—C6C—S6C | 118.9 (2) |
C65A—C66A—H66A | 119.9 | C8C—N7C—C5C | 102.8 (2) |
C61A—C66A—H66A | 119.9 | N7C—C8C—N9C | 114.9 (2) |
C64A—C67A—H67A | 109.5 | N7C—C8C—H8C | 122.5 |
C64A—C67A—H68A | 109.5 | N9C—C8C—H8C | 122.5 |
H67A—C67A—H68A | 109.5 | C8C—N9C—C4C | 105.8 (2) |
C64A—C67A—H69A | 109.5 | C8C—N9C—H9C | 127.1 |
H67A—C67A—H69A | 109.5 | C4C—N9C—H9C | 127.1 |
H68A—C67A—H69A | 109.5 | C6C—S6C—C61C | 103.13 (12) |
C6B—N1B—C2B | 118.2 (2) | C62C—C61C—C66C | 119.1 (3) |
N21B—C2B—N3B | 117.8 (2) | C62C—C61C—S6C | 120.5 (2) |
N21B—C2B—N1B | 115.2 (2) | C66C—C61C—S6C | 120.1 (2) |
N3B—C2B—N1B | 126.9 (2) | C61C—C62C—C63C | 120.1 (3) |
C2B—N21B—H21B | 120.0 | C61C—C62C—H62C | 120.0 |
C2B—N21B—H22B | 120.0 | C63C—C62C—H62C | 120.0 |
H21B—N21B—H22B | 120.0 | C62C—C63C—C64C | 121.7 (3) |
C4B—N3B—C2B | 112.1 (2) | C62C—C63C—H63C | 119.1 |
N3B—C4B—N9B | 127.5 (3) | C64C—C63C—H63C | 119.1 |
N3B—C4B—C5B | 125.9 (2) | C65C—C64C—C63C | 117.6 (3) |
N9B—C4B—C5B | 106.5 (2) | C65C—C64C—C67C | 121.8 (3) |
C4B—C5B—C6B | 116.8 (2) | C63C—C64C—C67C | 120.6 (3) |
C4B—C5B—N7B | 110.4 (2) | C64C—C65C—C66C | 121.5 (3) |
C6B—C5B—N7B | 132.8 (3) | C64C—C65C—H65C | 119.3 |
N1B—C6B—C5B | 119.9 (2) | C66C—C65C—H65C | 119.3 |
N1B—C6B—S6B | 121.4 (2) | C61C—C66C—C65C | 119.9 (3) |
C5B—C6B—S6B | 118.67 (19) | C61C—C66C—H66C | 120.0 |
C8B—N7B—C5B | 102.9 (2) | C65C—C66C—H66C | 120.0 |
N7B—C8B—N9B | 114.7 (2) | C64C—C67C—H67C | 109.5 |
N7B—C8B—H8B | 122.7 | C64C—C67C—H68C | 109.5 |
N9B—C8B—H8B | 122.7 | H67C—C67C—H68C | 109.5 |
C4B—N9B—C8B | 105.5 (2) | C64C—C67C—H69C | 109.5 |
C4B—N9B—H9B | 127.3 | H67C—C67C—H69C | 109.5 |
C8B—N9B—H9B | 127.3 | H68C—C67C—H69C | 109.5 |
C6B—S6B—C61B | 102.41 (13) | H1W—O1W—H2W | 110 (3) |
C6A—N1A—C2A—N3A | −1.6 (4) | C5B—N7B—C8B—N9B | −1.2 (3) |
C6A—N1A—C2A—N21A | −178.8 (2) | N3B—C4B—N9B—C8B | −178.0 (2) |
N21A—C2A—N3A—C5A | 178.6 (2) | C5B—C4B—N9B—C8B | 0.5 (3) |
N1A—C2A—N3A—C5A | 1.5 (4) | N7B—C8B—N9B—C4B | 0.5 (3) |
C2A—N3A—C5A—N9A | 179.2 (3) | N1B—C6B—S6B—C61B | 1.0 (2) |
C2A—N3A—C5A—C4A | −0.8 (4) | C5B—C6B—S6B—C61B | −179.8 (2) |
C6A—C4A—C5A—N3A | 0.2 (4) | C6B—S6B—C61B—C62B | 116.4 (2) |
N7A—C4A—C5A—N3A | −179.0 (2) | C6B—S6B—C61B—C66B | −66.6 (2) |
C6A—C4A—C5A—N9A | −179.8 (2) | C66B—C61B—C62B—C63B | 1.2 (4) |
N7A—C4A—C5A—N9A | 1.0 (3) | S6B—C61B—C62B—C63B | 178.2 (2) |
C2A—N1A—C6A—C4A | 0.9 (4) | C61B—C62B—C63B—C64B | 1.4 (4) |
C2A—N1A—C6A—S6A | −178.8 (2) | C62B—C63B—C64B—C65B | −2.4 (4) |
C5A—C4A—C6A—N1A | −0.2 (4) | C62B—C63B—C64B—C67B | 176.4 (3) |
N7A—C4A—C6A—N1A | 178.8 (3) | C63B—C64B—C65B—C66B | 1.0 (4) |
C5A—C4A—C6A—S6A | 179.48 (19) | C67B—C64B—C65B—C66B | −177.9 (3) |
N7A—C4A—C6A—S6A | −1.5 (4) | C64B—C65B—C66B—C61B | 1.5 (5) |
C5A—C4A—N7A—C8A | −1.0 (3) | C62B—C61B—C66B—C65B | −2.6 (4) |
C6A—C4A—N7A—C8A | −180.0 (3) | S6B—C61B—C66B—C65B | −179.5 (2) |
C4A—N7A—C8A—N9A | 0.6 (3) | C6C—N1C—C2C—N3C | −8.8 (4) |
N7A—C8A—N9A—C5A | 0.0 (3) | C6C—N1C—C2C—N21C | 172.2 (2) |
N3A—C5A—N9A—C8A | 179.4 (2) | N1C—C2C—N3C—C4C | 6.9 (3) |
C4A—C5A—N9A—C8A | −0.6 (3) | N21C—C2C—N3C—C4C | −174.2 (2) |
N1A—C6A—S6A—C61A | 0.2 (2) | C2C—N3C—C4C—N9C | 178.5 (2) |
C4A—C6A—S6A—C61A | −179.5 (2) | C2C—N3C—C4C—C5C | 1.7 (4) |
C6A—S6A—C61A—C66A | −109.7 (2) | C6C—C5C—C4C—N3C | −7.5 (4) |
C6A—S6A—C61A—C62A | 76.0 (2) | N7C—C5C—C4C—N3C | 175.9 (2) |
C66A—C61A—C62A—C63A | −1.6 (4) | C6C—C5C—C4C—N9C | 175.1 (2) |
S6A—C61A—C62A—C63A | 172.8 (2) | N7C—C5C—C4C—N9C | −1.4 (3) |
C61A—C62A—C63A—C64A | 1.4 (4) | C2C—N1C—C6C—C5C | 1.8 (3) |
C62A—C63A—C64A—C65A | 0.1 (4) | C2C—N1C—C6C—S6C | −178.12 (17) |
C62A—C63A—C64A—C67A | 179.4 (2) | C4C—C5C—C6C—N1C | 5.4 (4) |
C63A—C64A—C65A—C66A | −1.6 (4) | N7C—C5C—C6C—N1C | −179.0 (2) |
C67A—C64A—C65A—C66A | 179.2 (3) | C4C—C5C—C6C—S6C | −174.70 (18) |
C64A—C65A—C66A—C61A | 1.5 (4) | N7C—C5C—C6C—S6C | 0.9 (4) |
C62A—C61A—C66A—C65A | 0.1 (4) | C4C—C5C—N7C—C8C | 1.1 (3) |
S6A—C61A—C66A—C65A | −174.3 (2) | C6C—C5C—N7C—C8C | −174.7 (3) |
C6B—N1B—C2B—N21B | 177.7 (2) | C5C—N7C—C8C—N9C | −0.3 (3) |
C6B—N1B—C2B—N3B | −1.7 (4) | N7C—C8C—N9C—C4C | −0.6 (3) |
N21B—C2B—N3B—C4B | −178.6 (2) | N3C—C4C—N9C—C8C | −176.1 (2) |
N1B—C2B—N3B—C4B | 0.7 (4) | C5C—C4C—N9C—C8C | 1.2 (3) |
C2B—N3B—C4B—N9B | −179.7 (2) | N1C—C6C—S6C—C61C | −7.4 (2) |
C2B—N3B—C4B—C5B | 2.2 (4) | C5C—C6C—S6C—C61C | 172.8 (2) |
N3B—C4B—C5B—C6B | −3.8 (4) | C6C—S6C—C61C—C62C | −82.5 (3) |
N9B—C4B—C5B—C6B | 177.7 (2) | C6C—S6C—C61C—C66C | 103.0 (3) |
N3B—C4B—C5B—N7B | 177.2 (2) | C66C—C61C—C62C—C63C | −1.2 (5) |
N9B—C4B—C5B—N7B | −1.2 (3) | S6C—C61C—C62C—C63C | −175.7 (3) |
C2B—N1B—C6B—C5B | −0.1 (4) | C61C—C62C—C63C—C64C | 2.6 (5) |
C2B—N1B—C6B—S6B | 179.11 (18) | C62C—C63C—C64C—C65C | −2.6 (5) |
C4B—C5B—C6B—N1B | 2.6 (4) | C62C—C63C—C64C—C67C | 177.2 (3) |
N7B—C5B—C6B—N1B | −178.8 (2) | C63C—C64C—C65C—C66C | 1.3 (5) |
C4B—C5B—C6B—S6B | −176.65 (19) | C67C—C64C—C65C—C66C | −178.6 (3) |
N7B—C5B—C6B—S6B | 2.0 (4) | C62C—C61C—C66C—C65C | −0.1 (5) |
C4B—C5B—N7B—C8B | 1.5 (3) | S6C—C61C—C66C—C65C | 174.5 (2) |
C6B—C5B—N7B—C8B | −177.2 (3) | C64C—C65C—C66C—C61C | 0.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N3Ai | 0.88 | 2.17 | 3.046 (3) | 173 |
N21A—H22A···N21C | 0.88 | 2.46 | 3.226 (3) | 146 |
N9A—H9A···N7Bi | 0.88 | 2.09 | 2.948 (3) | 164 |
N21B—H21B···N3Cii | 0.88 | 2.20 | 3.062 (3) | 168 |
N21B—H22B···N7Aiii | 0.88 | 2.34 | 3.204 (3) | 168 |
N9B—H9B···O1W | 0.88 | 1.89 | 2.765 (3) | 173 |
N21C—H22C···N1A | 0.88 | 2.27 | 3.130 (3) | 164 |
N21C—H22C···N21A | 0.88 | 2.55 | 3.226 (3) | 134 |
N9C—H9C···N3Bii | 0.88 | 1.96 | 2.833 (3) | 174 |
O1W—H1W···N7Aiv | 0.85 (4) | 2.23 (4) | 3.075 (3) | 171 (3) |
O1W—H1W···S6Aiv | 0.85 (4) | 3.05 (3) | 3.452 (2) | 112 (3) |
O1W—H2W···N7Cv | 0.86 (4) | 2.01 (4) | 2.863 (3) | 174 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y, z−1; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C5H4ClN5 | C11H8ClN5S·0.5H2O | C12H11N5S·0.333H2O |
Mr | 169.58 | 286.74 | 263.32 |
Crystal system, space group | Tetragonal, P41212 | Monoclinic, C2/c | Triclinic, P1 |
Temperature (K) | 150 | 120 | 150 |
a, b, c (Å) | 7.0855 (10), 7.0855 (10), 26.990 (5) | 13.353 (3), 7.743 (2), 47.60 (1) | 10.8074 (2), 11.6355 (3), 15.3922 (3) |
α, β, γ (°) | 90, 90, 90 | 90, 95.85 (3), 90 | 85.468 (2), 83.265 (1), 79.7992 (9) |
V (Å3) | 1355.0 (4) | 4896 (2) | 1888.46 (7) |
Z | 8 | 16 | 6 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.49 | 0.48 | 0.25 |
Crystal size (mm) | 0.15 × 0.08 × 0.07 | 0.20 × 0.16 × 0.05 | 0.12 × 0.12 × 0.01 |
Data collection | |||
Diffractometer | Bruker–Nonius KappaCCD area-detector diffractometer | Bruker–Nonius KappaCCD area-detector diffractometer | Bruker–Nonius KappaCCD area detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) | Multi-scan (SORTAV; Blessing, 1995) | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.910, 0.964 | 0.737, 0.982 | 0.931, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4943, 1535, 1151 | 10871, 3842, 3045 | 36016, 8568, 4357 |
Rint | 0.065 | 0.060 | 0.111 |
(sin θ/λ)max (Å−1) | 0.649 | 0.595 | 0.650 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.083, 1.04 | 0.040, 0.105, 1.11 | 0.055, 0.128, 0.94 |
No. of reflections | 1535 | 3842 | 8568 |
No. of parameters | 100 | 342 | 507 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.31 | 0.47, −0.57 | 0.28, −0.30 |
Absolute structure | Flack (1983), 548 Friedel pairs | ? | ? |
Absolute structure parameter | 0.00 (10) | ? | ? |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N1i | 0.88 | 2.22 | 3.019 (3) | 150 |
N21—H22···N3ii | 0.88 | 2.15 | 3.027 (3) | 174 |
N9—H9···N7iii | 0.88 | 2.02 | 2.888 (3) | 168 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/4; (ii) −x+1/2, y+1/2, −z+1/4; (iii) y, x−1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N7Ai | 0.88 | 2.22 | 3.072 (3) | 163 |
N21A—H22A···N1Aii | 0.88 | 2.49 | 3.300 (3) | 154 |
N21A—H22A···S6Ai | 0.88 | 2.84 | 3.326 (2) | 117 |
N9A—H9A···N3Biii | 0.88 | 2.19 | 2.965 (3) | 146 |
N21B—H21B···N7Biv | 0.88 | 2.25 | 3.077 (3) | 158 |
N21B—H22B···Cl6Bv | 0.88 | 2.72 | 3.475 (2) | 145 |
N21B—H22B···S6Biv | 0.88 | 2.92 | 3.415 (2) | 118 |
N9B—H9B···O1Wvi | 0.88 | 1.89 | 2.757 (3) | 166 |
O1W—H1W···S6Biv | 0.84 (4) | 3.05 (4) | 3.668 (2) | 132 (3) |
O1W—H2W···N3Avii | 0.85 (4) | 1.91 (4) | 2.756 (3) | 174 (3) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) −x, y, −z+1/2; (iii) −x+1, y, −z+1/2; (iv) x, y+1, z; (v) −x+1/2, −y+1/2, −z; (vi) x+1/2, y−1/2, z; (vii) −x+1/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N3Ai | 0.88 | 2.17 | 3.046 (3) | 173 |
N21A—H22A···N21C | 0.88 | 2.46 | 3.226 (3) | 146 |
N9A—H9A···N7Bi | 0.88 | 2.09 | 2.948 (3) | 164 |
N21B—H21B···N3Cii | 0.88 | 2.20 | 3.062 (3) | 168 |
N21B—H22B···N7Aiii | 0.88 | 2.34 | 3.204 (3) | 168 |
N9B—H9B···O1W | 0.88 | 1.89 | 2.765 (3) | 173 |
N21C—H22C···N1A | 0.88 | 2.27 | 3.130 (3) | 164 |
N21C—H22C···N21A | 0.88 | 2.55 | 3.226 (3) | 134 |
N9C—H9C···N3Bii | 0.88 | 1.96 | 2.833 (3) | 174 |
O1W—H1W···N7Aiv | 0.85 (4) | 2.23 (4) | 3.075 (3) | 171 (3) |
O1W—H1W···S6Aiv | 0.85 (4) | 3.05 (3) | 3.452 (2) | 112 (3) |
O1W—H2W···N7Cv | 0.86 (4) | 2.01 (4) | 2.863 (3) | 174 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y, z−1; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z. |
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Purine bases play an important role in the chemistry of life. Two purine bases, adenine and guanine, are found as major components of DNA and RNA. In these systems, attachment to the deoxyribose or ribose groups occurs via N9. Similarly, of the 549 reported structures (Cambridge Structural Database, April 2002 release; Allen, 2002) containing a purine group, the vast majority also contain N9 substituents other than an H atom, with only 92 purine structures exhibiting an N9—H group. There are 34 2-aminopurine structures, of which only two have N9—H; these are N-(2-amino-6-purinyl)pyridinium chloride dihydrate (Jaskolski et al., 1987) and potassium 2-amino-6-sulfinatopurine monohydrate (Horn & Tiekink, 1995). The hydrogen-bonding patterns in both are dominated by the counter-ions. We report here the crystal structures of three 2-aminopurine derivatives containing N9—H, namely 2-amino-6-chloropurine, (I), 2-amino-6-(4-chlorophenylthio)purine hemihydrate, (II), and 2-amino-6-(4-methylphenylthio)purine 0.33-hydrate, (III). Compounds (II) and (III) were both derived by the nucleophilic addition of a thiophenol derivative to (I).
Compound (I) is a flat molecule [r.m.s. deviation 0.010 (2) Å] with three strong hydrogen-bond donor atoms and three strong hydrogen-bond acceptor atoms (neglecting the N atom in NH2), plus the Cl atom that can be considered as a weak acceptor (Fig. 1). This equality in numbers of strong hydrogen-bonding agents is reflected in the hydrogen-bonding network with all possible strong hydrogen-bonding sites occupied (Table 1). N9—H associates with N7 and creates a flat hydrogen-bond chain with molecules of alternating directions inclined to the (001) plane (Fig. 2). The associations between atoms N2, N31 and N4 form a convoluted hydrogen-bonded ribbon network similar to 2-aminopyrimidine and subsequent derivatives (Lynch et al., 2002). Thus, each molecule associates with two molecules via pairwise interactions and with two others through single interactions. The Cl atom resides in a position that is approximated by H8(1 + y, x, −z) [3.121 (3) Å], but the distance is too far to be listed as a formal C—H···Cl close contact.
The asymmetric unit of (II) consists of two unique 2-amino-6-(4-chlorophenylthio)purine molecules with one water molecule (Fig. 3). This combination gives eight strong hydrogen-bond donors and seven strong acceptors per asymmetric unit (neglecting the N atoms of the NH2 groups), plus two S atoms and two Cl atoms, both considered to act as weak hydrogen-bonding acceptors. All of these sites are involved in the hydrogen-bonding array, except for two acceptors, N1B and Cl6A (Table 2), although the Cl atom is approached by H8B(−1 + x,1 + y, z) [2.733 (3) Å]. Molecules A and B and the water molecule form a hydrogen-bonded ring [graph-set notation R33(10); Bernstein et al., 1995] through N9A—H···N3B, N9B—H···O1W and O1W—H···N3A hydrogen bonds. The 2-amino group of molecule A associates with N7A through one H atom and with both N1A and S6A through the H atom. The 2-amino group of molecule B is involved in a similar arrangement, with one H associating with N7B and the other associating with both Cl6B and S6B. The remaining water H atom also associates with S6B. The resulting network is very complex and difficult to represent in a single-view packing diagram (Fig. 4). The phenyl rings are significantly inclined to the purine rings with respective dihedral angles for molecules A and B of 72.21 (6) and 79.57 (8)°. Such angles allow the phenyl rings of molecule A to form alternating slipped-stacks with the purine rings of like molecules [interlayer distances ca 3.40 (4) Å and angle 2.26 (2)°]. For molecule B, the slipped-stacks are only formed by symmetry-related phenyl rings of alternating directions [interlayer distance 3.483 (3) Å], which are coplanar by symmetry.
The asymmetric unit of (III) consists of three unique 2-amino-6-(4-methylphenylthio)purine molecules and one water molecule (Fig. 5). This combination gives eight strong hydrogen-bond donors, seven strong acceptors (neglecting the N atoms of the NH2 groups) and three S atoms. Molecules A and B associate via a single hydrogen bond (N9A—H···N7B) and also via a N21A—H···N3A dimer to form a linked tetramer that is `capped' at both ends by an association from N9B—H to the water molecule. This water molecule, O1W, through one H atom, then associates to N7C. Molecule C, through N9C—H and N3C, forms a dimer with N3B and N21B—H. The full list of hydrogen bonds in (III) is given in Table 3 although additional noteworthy interactions are the two three-centre associations, one from N21C to N1A and N21A (note the use in this structure of a NH2 group as an hydrogen-bond acceptor) and the other from the water molecule to atoms N7A and S6A. There are no close contacts with one H atom of N21C. Again, the hydrogen-bonding network is very extensive and difficult to represent in a single-view packing diagram (Fig. 6). The dihedral angles between the phenyl ring and the purine for molecules A, B and C are 73.08 (7), 63.21 (8) and 80.80 (8)°, respectively, and again allow for slipped-stacks. A triplet of phenyl-A, purine-C and purine-B has the respective interlayer distances and angles of 3.2 (2) Å and 12.34 (4)°, and 3.4 (1) Å and 15.92 (4)°, whereas a tetramer of purine-A, phenyl-C, phenyl-C and purine-A has similar values of 3.62 (4) Å and 15.46 (4)°, and 3.679 (3) Å and 0.02 (4)°. The only ring system not to partake in stacking arrangements is phenyl-B.