Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110023188/sk3377sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110023188/sk3377Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110023188/sk3377IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110023188/sk3377IIIsup4.hkl |
CCDC references: 786823; 786824; 786825
For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C10H15N3O2 | F(000) = 896 |
Mr = 209.25 | Dx = 1.280 Mg m−3 |
Monoclinic, P21/c | Melting point: 381 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8148 (5) Å | Cell parameters from 5295 reflections |
b = 20.9889 (14) Å | θ = 2.5–30.0° |
c = 13.2464 (9) Å | µ = 0.09 mm−1 |
β = 91.210 (2)° | T = 140 K |
V = 2172.2 (2) Å3 | Thin plate, yellow |
Z = 8 | 0.22 × 0.18 × 0.04 mm |
Bruker SMART 6000 CCD area-detector diffractometer | 4717 independent reflections |
Radiation source: sealed tube | 3307 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.559, Tmax = 1.000 | k = −26→26 |
23033 measured reflections | l = −15→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.139 | All H-atom parameters refined |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0898P)2] where P = (Fo2 + 2Fc2)/3 |
4717 reflections | (Δ/σ)max = 0.001 |
391 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.63355 (16) | 0.35444 (6) | 0.45013 (9) | 0.0443 (3) | |
O2 | 0.68500 (16) | 0.26199 (6) | 0.38341 (9) | 0.0426 (3) | |
O3 | 0.15779 (15) | 0.37249 (5) | 0.88626 (9) | 0.0396 (3) | |
O4 | 0.13061 (14) | 0.27486 (5) | 0.93728 (8) | 0.0353 (3) | |
N1 | 0.57409 (17) | 0.15831 (7) | 0.46880 (10) | 0.0327 (3) | |
H1N | 0.623 (2) | 0.1747 (9) | 0.4172 (16) | 0.046 (5)* | |
N2 | 0.29478 (16) | 0.19290 (6) | 0.78284 (10) | 0.0302 (3) | |
H2N | 0.260 (2) | 0.2209 (8) | 0.8272 (14) | 0.039 (5)* | |
N3 | 0.62171 (16) | 0.29501 (7) | 0.45286 (10) | 0.0331 (3) | |
N4 | −0.03406 (16) | 0.24834 (6) | 1.10349 (9) | 0.0256 (3) | |
H4N | 0.029 (2) | 0.2352 (7) | 1.0560 (13) | 0.023 (4)* | |
N5 | −0.23966 (17) | 0.42974 (6) | 1.27911 (11) | 0.0312 (3) | |
H5N | −0.275 (2) | 0.4031 (8) | 1.3256 (14) | 0.031 (4)* | |
N6 | 0.10800 (15) | 0.33338 (6) | 0.95034 (9) | 0.0287 (3) | |
C1 | 0.51748 (17) | 0.19849 (7) | 0.54033 (11) | 0.0270 (3) | |
C2 | 0.43502 (18) | 0.17483 (7) | 0.62573 (12) | 0.0273 (3) | |
H2 | 0.425 (2) | 0.1302 (8) | 0.6310 (13) | 0.033 (4)* | |
C3 | 0.37305 (17) | 0.21530 (7) | 0.70053 (11) | 0.0259 (3) | |
C4 | 0.39349 (18) | 0.28247 (7) | 0.69040 (12) | 0.0285 (3) | |
H4 | 0.357 (2) | 0.3114 (8) | 0.7459 (13) | 0.035 (4)* | |
C5 | 0.47428 (19) | 0.30596 (8) | 0.60924 (12) | 0.0291 (3) | |
H5 | 0.489 (2) | 0.3494 (8) | 0.6026 (12) | 0.030 (4)* | |
C6 | 0.53809 (18) | 0.26590 (7) | 0.53286 (11) | 0.0278 (3) | |
C7 | 0.5517 (2) | 0.08965 (8) | 0.46965 (13) | 0.0374 (4) | |
H7B | 0.430 (2) | 0.0799 (8) | 0.4721 (13) | 0.038 (5)* | |
H7A | 0.608 (2) | 0.0719 (7) | 0.5306 (14) | 0.030 (4)* | |
C8 | 0.6307 (3) | 0.06151 (11) | 0.37664 (17) | 0.0522 (5) | |
H8C | 0.578 (3) | 0.0780 (9) | 0.3171 (17) | 0.054 (6)* | |
H8B | 0.751 (3) | 0.0719 (11) | 0.3751 (19) | 0.076 (7)* | |
H8A | 0.612 (3) | 0.0142 (11) | 0.3727 (16) | 0.062 (6)* | |
C9 | 0.2685 (2) | 0.12618 (8) | 0.80404 (13) | 0.0332 (4) | |
H9B | 0.384 (2) | 0.1041 (7) | 0.8120 (12) | 0.029 (4)* | |
H9A | 0.206 (2) | 0.1051 (7) | 0.7462 (13) | 0.031 (4)* | |
C10 | 0.1652 (3) | 0.11873 (9) | 0.89908 (14) | 0.0430 (4) | |
H10C | 0.235 (3) | 0.1353 (9) | 0.9561 (16) | 0.050 (5)* | |
H10B | 0.145 (2) | 0.0720 (9) | 0.9110 (15) | 0.047 (5)* | |
H10A | 0.047 (3) | 0.1402 (10) | 0.8899 (16) | 0.058 (6)* | |
C11 | −0.04718 (17) | 0.31209 (7) | 1.11016 (10) | 0.0234 (3) | |
C12 | −0.13377 (18) | 0.34025 (7) | 1.19008 (11) | 0.0249 (3) | |
H12 | −0.189 (2) | 0.3130 (7) | 1.2394 (13) | 0.026 (4)* | |
C13 | −0.14897 (18) | 0.40569 (7) | 1.20148 (11) | 0.0266 (3) | |
C14 | −0.0687 (2) | 0.44721 (7) | 1.13121 (12) | 0.0317 (4) | |
H14 | −0.066 (2) | 0.4926 (8) | 1.1394 (12) | 0.030 (4)* | |
C15 | 0.0135 (2) | 0.42091 (8) | 1.05125 (12) | 0.0312 (4) | |
H15 | 0.067 (2) | 0.4482 (9) | 1.0051 (15) | 0.041 (5)* | |
C16 | 0.02458 (17) | 0.35485 (7) | 1.03691 (11) | 0.0263 (3) | |
C17 | −0.0861 (2) | 0.20518 (7) | 1.18347 (12) | 0.0270 (3) | |
H17B | −0.022 (2) | 0.2152 (7) | 1.2466 (13) | 0.030 (4)* | |
H17A | −0.208 (2) | 0.2112 (7) | 1.1962 (11) | 0.024 (4)* | |
C18 | −0.0550 (3) | 0.13704 (8) | 1.15234 (14) | 0.0367 (4) | |
H18C | 0.066 (3) | 0.1310 (8) | 1.1371 (15) | 0.050 (5)* | |
H18B | −0.085 (2) | 0.1086 (9) | 1.2086 (16) | 0.047 (5)* | |
H18A | −0.121 (3) | 0.1255 (9) | 1.0945 (18) | 0.053 (6)* | |
C19 | −0.2385 (2) | 0.49620 (8) | 1.30884 (15) | 0.0402 (4) | |
H19B | −0.122 (3) | 0.5078 (9) | 1.3259 (15) | 0.051 (5)* | |
H19A | −0.273 (3) | 0.5236 (10) | 1.2515 (18) | 0.067 (6)* | |
C20 | −0.3581 (3) | 0.50703 (9) | 1.39423 (19) | 0.0538 (6) | |
H20C | −0.354 (2) | 0.5499 (10) | 1.4134 (15) | 0.045 (5)* | |
H20B | −0.322 (3) | 0.4814 (12) | 1.449 (2) | 0.083 (8)* | |
H20A | −0.473 (4) | 0.4959 (11) | 1.374 (2) | 0.085 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0557 (8) | 0.0405 (7) | 0.0372 (7) | −0.0124 (6) | 0.0086 (6) | 0.0075 (5) |
O2 | 0.0445 (7) | 0.0570 (8) | 0.0267 (6) | −0.0027 (6) | 0.0136 (5) | 0.0021 (5) |
O3 | 0.0446 (7) | 0.0476 (7) | 0.0271 (6) | −0.0039 (5) | 0.0118 (5) | 0.0098 (5) |
O4 | 0.0422 (7) | 0.0361 (7) | 0.0279 (6) | −0.0003 (5) | 0.0101 (5) | −0.0008 (5) |
N1 | 0.0343 (7) | 0.0385 (8) | 0.0256 (7) | 0.0033 (6) | 0.0079 (6) | −0.0007 (6) |
N2 | 0.0294 (7) | 0.0332 (7) | 0.0281 (7) | 0.0001 (5) | 0.0065 (6) | 0.0025 (6) |
N3 | 0.0307 (7) | 0.0428 (8) | 0.0259 (7) | −0.0049 (6) | 0.0023 (6) | 0.0059 (6) |
N4 | 0.0282 (6) | 0.0273 (7) | 0.0214 (6) | 0.0006 (5) | 0.0060 (5) | 0.0018 (5) |
N5 | 0.0367 (7) | 0.0241 (7) | 0.0334 (8) | 0.0001 (5) | 0.0116 (6) | 0.0030 (5) |
N6 | 0.0257 (6) | 0.0375 (7) | 0.0229 (7) | −0.0017 (5) | 0.0019 (5) | 0.0049 (5) |
C1 | 0.0198 (7) | 0.0371 (8) | 0.0242 (7) | 0.0040 (6) | −0.0010 (6) | 0.0001 (6) |
C2 | 0.0243 (7) | 0.0287 (8) | 0.0289 (8) | 0.0016 (6) | 0.0011 (6) | 0.0026 (6) |
C3 | 0.0184 (7) | 0.0352 (8) | 0.0242 (7) | 0.0021 (6) | 0.0005 (6) | 0.0023 (6) |
C4 | 0.0228 (7) | 0.0344 (8) | 0.0282 (8) | 0.0025 (6) | 0.0018 (6) | −0.0011 (6) |
C5 | 0.0260 (8) | 0.0307 (8) | 0.0306 (8) | −0.0004 (6) | −0.0002 (6) | 0.0020 (6) |
C6 | 0.0226 (7) | 0.0382 (8) | 0.0225 (8) | −0.0012 (6) | 0.0009 (6) | 0.0050 (6) |
C7 | 0.0408 (10) | 0.0372 (9) | 0.0344 (10) | 0.0079 (7) | 0.0033 (8) | −0.0008 (7) |
C8 | 0.0692 (15) | 0.0481 (12) | 0.0395 (12) | 0.0126 (10) | 0.0070 (10) | −0.0078 (9) |
C9 | 0.0329 (9) | 0.0353 (9) | 0.0313 (9) | −0.0011 (7) | 0.0012 (7) | 0.0064 (7) |
C10 | 0.0519 (12) | 0.0488 (11) | 0.0284 (9) | −0.0150 (9) | 0.0028 (8) | 0.0079 (8) |
C11 | 0.0206 (7) | 0.0287 (7) | 0.0209 (7) | −0.0010 (5) | −0.0005 (5) | 0.0046 (5) |
C12 | 0.0230 (7) | 0.0286 (8) | 0.0233 (7) | −0.0014 (6) | 0.0030 (6) | 0.0058 (6) |
C13 | 0.0231 (7) | 0.0293 (8) | 0.0274 (8) | 0.0015 (6) | 0.0025 (6) | 0.0054 (6) |
C14 | 0.0359 (8) | 0.0262 (8) | 0.0331 (9) | 0.0022 (6) | 0.0066 (7) | 0.0088 (6) |
C15 | 0.0307 (8) | 0.0338 (8) | 0.0293 (8) | 0.0012 (6) | 0.0051 (6) | 0.0121 (7) |
C16 | 0.0226 (7) | 0.0345 (8) | 0.0220 (7) | 0.0008 (6) | 0.0022 (6) | 0.0059 (6) |
C17 | 0.0291 (8) | 0.0277 (8) | 0.0243 (8) | −0.0017 (6) | 0.0031 (6) | 0.0037 (6) |
C18 | 0.0462 (10) | 0.0281 (8) | 0.0359 (10) | −0.0003 (7) | 0.0074 (8) | 0.0034 (7) |
C19 | 0.0437 (10) | 0.0252 (8) | 0.0520 (11) | 0.0004 (7) | 0.0120 (9) | −0.0005 (8) |
C20 | 0.0760 (16) | 0.0283 (10) | 0.0579 (14) | −0.0012 (10) | 0.0241 (12) | −0.0115 (9) |
O1—N3 | 1.2514 (18) | C8—H8C | 0.95 (2) |
O2—N3 | 1.2611 (17) | C8—H8B | 0.97 (2) |
O3—N6 | 1.2490 (16) | C8—H8A | 1.00 (2) |
O4—N6 | 1.2534 (16) | C9—C10 | 1.518 (2) |
N1—C1 | 1.3498 (19) | C9—H9B | 1.021 (16) |
N1—C7 | 1.452 (2) | C9—H9A | 1.002 (17) |
N1—H1N | 0.86 (2) | C10—H10C | 0.98 (2) |
N2—C3 | 1.3462 (19) | C10—H10B | 1.005 (19) |
N2—C9 | 1.444 (2) | C10—H10A | 1.03 (2) |
N2—H2N | 0.878 (19) | C11—C12 | 1.399 (2) |
N3—C6 | 1.3974 (18) | C11—C16 | 1.4438 (19) |
N4—C11 | 1.3449 (18) | C12—C13 | 1.387 (2) |
N4—C17 | 1.4583 (18) | C12—H12 | 0.975 (16) |
N4—H4N | 0.854 (17) | C13—C14 | 1.430 (2) |
N5—C13 | 1.3584 (19) | C14—C15 | 1.367 (2) |
N5—C19 | 1.449 (2) | C14—H14 | 0.960 (16) |
N5—H5N | 0.881 (18) | C15—C16 | 1.402 (2) |
N6—C16 | 1.4053 (19) | C15—H15 | 0.944 (19) |
C1—C2 | 1.404 (2) | C17—C18 | 1.510 (2) |
C1—C6 | 1.428 (2) | C17—H17B | 0.989 (17) |
C2—C3 | 1.399 (2) | C17—H17A | 0.977 (16) |
C2—H2 | 0.942 (17) | C18—H18C | 0.98 (2) |
C3—C4 | 1.426 (2) | C18—H18B | 0.99 (2) |
C4—C5 | 1.351 (2) | C18—H18A | 0.95 (2) |
C4—H4 | 0.998 (17) | C19—C20 | 1.500 (3) |
C5—C6 | 1.414 (2) | C19—H19B | 0.96 (2) |
C5—H5 | 0.923 (17) | C19—H19A | 0.99 (2) |
C7—C8 | 1.510 (3) | C20—H20C | 0.93 (2) |
C7—H7B | 0.974 (18) | C20—H20B | 0.94 (3) |
C7—H7A | 0.985 (18) | C20—H20A | 0.96 (3) |
C1—N1—C7 | 124.98 (14) | N2—C9—H9A | 110.4 (9) |
C1—N1—H1N | 117.7 (12) | C10—C9—H9A | 109.2 (9) |
C7—N1—H1N | 117.2 (12) | H9B—C9—H9A | 107.1 (13) |
C3—N2—C9 | 124.42 (14) | C9—C10—H10C | 107.9 (12) |
C3—N2—H2N | 117.5 (12) | C9—C10—H10B | 108.5 (11) |
C9—N2—H2N | 118.1 (12) | H10C—C10—H10B | 108.0 (16) |
O1—N3—O2 | 119.76 (12) | C9—C10—H10A | 110.3 (12) |
O1—N3—C6 | 119.59 (13) | H10C—C10—H10A | 114.4 (17) |
O2—N3—C6 | 120.65 (13) | H10B—C10—H10A | 107.6 (15) |
C11—N4—C17 | 123.19 (12) | N4—C11—C12 | 120.57 (12) |
C11—N4—H4N | 114.5 (10) | N4—C11—C16 | 122.90 (13) |
C17—N4—H4N | 120.7 (10) | C12—C11—C16 | 116.53 (13) |
C13—N5—C19 | 124.26 (13) | C13—C12—C11 | 122.99 (13) |
C13—N5—H5N | 118.1 (11) | C13—C12—H12 | 117.9 (9) |
C19—N5—H5N | 114.9 (11) | C11—C12—H12 | 119.1 (9) |
O3—N6—O4 | 120.23 (12) | N5—C13—C12 | 119.84 (13) |
O3—N6—C16 | 120.02 (13) | N5—C13—C14 | 120.64 (13) |
O4—N6—C16 | 119.75 (12) | C12—C13—C14 | 119.52 (13) |
N1—C1—C2 | 120.48 (14) | C15—C14—C13 | 118.58 (14) |
N1—C1—C6 | 122.10 (13) | C15—C14—H14 | 118.7 (10) |
C2—C1—C6 | 117.42 (13) | C13—C14—H14 | 122.7 (10) |
C3—C2—C1 | 121.82 (14) | C14—C15—C16 | 122.39 (14) |
C3—C2—H2 | 121.3 (11) | C14—C15—H15 | 118.7 (11) |
C1—C2—H2 | 116.8 (11) | C16—C15—H15 | 118.9 (11) |
N2—C3—C2 | 122.11 (14) | C15—C16—N6 | 117.30 (13) |
N2—C3—C4 | 118.38 (13) | C15—C16—C11 | 119.85 (13) |
C2—C3—C4 | 119.51 (13) | N6—C16—C11 | 122.85 (13) |
C5—C4—C3 | 119.40 (14) | N4—C17—C18 | 109.94 (13) |
C5—C4—H4 | 120.6 (10) | N4—C17—H17B | 109.8 (9) |
C3—C4—H4 | 119.8 (10) | C18—C17—H17B | 110.5 (9) |
C4—C5—C6 | 121.99 (15) | N4—C17—H17A | 109.4 (9) |
C4—C5—H5 | 119.9 (10) | C18—C17—H17A | 109.4 (8) |
C6—C5—H5 | 118.1 (10) | H17B—C17—H17A | 107.8 (13) |
N3—C6—C5 | 117.39 (14) | C17—C18—H18C | 109.9 (11) |
N3—C6—C1 | 122.76 (13) | C17—C18—H18B | 108.9 (11) |
C5—C6—C1 | 119.84 (13) | H18C—C18—H18B | 109.0 (16) |
N1—C7—C8 | 109.30 (15) | C17—C18—H18A | 112.0 (12) |
N1—C7—H7B | 109.1 (10) | H18C—C18—H18A | 108.2 (17) |
C8—C7—H7B | 111.2 (11) | H18B—C18—H18A | 108.8 (17) |
N1—C7—H7A | 109.3 (9) | N5—C19—C20 | 110.51 (14) |
C8—C7—H7A | 109.7 (9) | N5—C19—H19B | 107.9 (11) |
H7B—C7—H7A | 108.2 (14) | C20—C19—H19B | 112.6 (12) |
C7—C8—H8C | 111.0 (12) | N5—C19—H19A | 110.6 (13) |
C7—C8—H8B | 110.1 (15) | C20—C19—H19A | 109.1 (13) |
H8C—C8—H8B | 108 (2) | H19B—C19—H19A | 106.0 (17) |
C7—C8—H8A | 111.6 (13) | C19—C20—H20C | 109.3 (12) |
H8C—C8—H8A | 104.9 (17) | C19—C20—H20B | 108.3 (16) |
H8B—C8—H8A | 111.2 (18) | H20C—C20—H20B | 109.4 (19) |
N2—C9—C10 | 109.98 (14) | C19—C20—H20A | 110.0 (17) |
N2—C9—H9B | 109.3 (9) | H20C—C20—H20A | 109.9 (18) |
C10—C9—H9B | 110.7 (9) | H20B—C20—H20A | 110 (2) |
N6—O4—H2N—N2 | −142 (7) | C3—N2—C9—C10 | −175.97 (15) |
O4—H2N—N2—C3 | 143 (7) | C11—C12—C13—C14 | −2.2 (2) |
O4—H2N—N2—C9 | −38 (8) | C12—C13—C14—C15 | 3.5 (2) |
C1—C2—C3—C4 | 0.0 (2) | C13—C14—C15—C16 | −1.3 (2) |
C2—C3—C4—C5 | −0.8 (2) | C14—C15—C16—C11 | −2.3 (2) |
C3—C4—C5—C6 | 0.7 (2) | C15—C16—C11—C12 | 3.5 (2) |
C4—C5—C6—C1 | 0.1 (2) | C16—C11—C12—C13 | −1.3 (2) |
C5—C6—C1—C2 | −0.8 (2) | C11—C16—N6—O3 | 175.36 (13) |
C6—C1—C2—C3 | 0.8 (2) | C11—C16—N6—O4 | −3.9 (2) |
C1—C6—N3—O1 | 179.09 (13) | C15—C16—N6—O3 | −5.1 (2) |
C1—C6—N3—O2 | −0.8 (2) | C15—C16—N6—O4 | 175.59 (13) |
C5—C6—N3—O1 | −1.7 (2) | C12—C11—N4—C17 | −8.6 (2) |
C5—C6—N3—O2 | 178.42 (14) | C16—C11—N4—C17 | 171.70 (14) |
C2—C1—N1—C7 | 2.4 (2) | C11—N4—C17—C18 | 179.93 (14) |
C6—C1—N1—C7 | −177.53 (15) | C12—C13—N5—C19 | 168.42 (16) |
C1—N1—C7—C8 | 179.41 (16) | C14—C13—N5—C19 | −11.5 (2) |
C2—C3—N2—C9 | 1.0 (2) | C13—N5—C19—C20 | 177.56 (18) |
C4—C3—N2—C9 | −178.67 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.86 (2) | 1.950 (19) | 2.6091 (18) | 132.3 (17) |
N2—H2N···O4 | 0.878 (19) | 2.12 (2) | 2.9835 (18) | 167.8 (16) |
N4—H4N···O4 | 0.854 (17) | 1.961 (17) | 2.6330 (16) | 134.8 (13) |
N5—H5N···O1i | 0.881 (18) | 2.079 (18) | 2.9507 (18) | 170.0 (15) |
Symmetry code: (i) x−1, y, z+1. |
C11H14N4O2 | F(000) = 496 |
Mr = 234.26 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/c | Melting point: 420 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.988 (8) Å | Cell parameters from 1800 reflections |
b = 4.865 (4) Å | θ = 2.6–33.0° |
c = 21.220 (18) Å | µ = 0.10 mm−1 |
β = 91.62 (4)° | T = 150 K |
V = 1133.9 (17) Å3 | Parallelepiped, yellow |
Z = 4 | 0.55 × 0.40 × 0.18 mm |
Bruker SMART 6000 CCD area-detector diffractometer | 2745 independent reflections |
Radiation source: sealed tube | 2346 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 28.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.819, Tmax = 1.000 | k = −6→6 |
11551 measured reflections | l = −28→21 |
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0676P)2 + 0.4024P] where P = (Fo2 + 2Fc2)/3 |
2745 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.16723 (11) | −0.0579 (3) | 0.18323 (5) | 0.0577 (3) | |
O2 | 0.07049 (9) | 0.2693 (3) | 0.22861 (5) | 0.0503 (3) | |
N1 | 0.38855 (11) | 0.6007 (3) | 0.46717 (6) | 0.0475 (3) | |
N2 | 0.15835 (11) | 0.4849 (3) | 0.33291 (6) | 0.0484 (3) | |
H2N | 0.099 (2) | 0.462 (4) | 0.3041 (10) | 0.068 (6)* | |
N3 | 0.15951 (10) | 0.1123 (3) | 0.22631 (5) | 0.0387 (3) | |
N4 | 0.55259 (9) | 0.1149 (2) | 0.39957 (6) | 0.0338 (3) | |
H4N | 0.5517 (15) | 0.213 (4) | 0.4340 (8) | 0.042 (4)* | |
C1 | 0.35495 (10) | 0.2972 (3) | 0.36893 (6) | 0.0299 (3) | |
C2 | 0.25174 (11) | 0.3112 (3) | 0.32603 (6) | 0.0319 (3) | |
C3 | 0.25533 (11) | 0.1278 (3) | 0.27327 (6) | 0.0317 (3) | |
C4 | 0.35196 (12) | −0.0547 (3) | 0.26620 (6) | 0.0365 (3) | |
H4 | 0.3481 (16) | −0.176 (4) | 0.2316 (8) | 0.049 (5)* | |
C5 | 0.44946 (12) | −0.0650 (3) | 0.30750 (6) | 0.0358 (3) | |
H5 | 0.5142 (16) | −0.192 (4) | 0.3011 (8) | 0.047 (4)* | |
C6 | 0.45423 (11) | 0.1149 (2) | 0.35995 (6) | 0.0298 (3) | |
C7 | 0.36767 (11) | 0.4716 (3) | 0.42273 (6) | 0.0337 (3) | |
C8A | 0.13650 (16) | 0.6884 (4) | 0.38084 (9) | 0.0376 (4) | 0.75 |
H8AB | 0.210 (2) | 0.786 (4) | 0.3940 (10) | 0.040 (5)* | 0.75 |
H8AA | 0.081 (2) | 0.832 (5) | 0.3602 (10) | 0.042 (6)* | 0.75 |
C9A | 0.0773 (2) | 0.5509 (7) | 0.43544 (14) | 0.0539 (6) | 0.75 |
H9AC | 0.129 (2) | 0.411 (5) | 0.4545 (12) | 0.058 (7)* | 0.75 |
H9AB | 0.003 (2) | 0.465 (5) | 0.4220 (12) | 0.058 (7)* | 0.75 |
H9AA | 0.062 (3) | 0.699 (7) | 0.4676 (15) | 0.078 (9)* | 0.75 |
C8B | 0.0986 (5) | 0.5105 (12) | 0.4037 (3) | 0.0309 (11) | 0.25 |
H8BA | 0.0152 | 0.4335 | 0.4036 | 0.037* | 0.25 |
H8BB | 0.1495 | 0.4142 | 0.4360 | 0.037* | 0.25 |
C9B | 0.0972 (4) | 0.8183 (12) | 0.4156 (2) | 0.0349 (10) | 0.25 |
H9BA | 0.0631 | 0.8548 | 0.4570 | 0.052* | 0.25 |
H9BB | 0.0471 | 0.9089 | 0.3828 | 0.052* | 0.25 |
H9BC | 0.1805 | 0.8898 | 0.4148 | 0.052* | 0.25 |
C10 | 0.65577 (13) | −0.0717 (3) | 0.39138 (7) | 0.0408 (3) | |
H10A | 0.6904 (17) | −0.046 (4) | 0.3459 (9) | 0.053 (5)* | |
H10B | 0.6260 (16) | −0.260 (4) | 0.3964 (8) | 0.049 (5)* | |
C11 | 0.75812 (14) | −0.0090 (4) | 0.43797 (8) | 0.0502 (4) | |
H11A | 0.8283 (19) | −0.126 (4) | 0.4292 (9) | 0.060 (5)* | |
H11B | 0.7862 (18) | 0.185 (4) | 0.4321 (9) | 0.062 (6)* | |
H11C | 0.732 (2) | −0.025 (5) | 0.4802 (11) | 0.074 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0524 (7) | 0.0781 (8) | 0.0418 (6) | −0.0049 (6) | −0.0143 (5) | −0.0215 (6) |
O2 | 0.0388 (5) | 0.0625 (7) | 0.0481 (6) | 0.0005 (5) | −0.0225 (4) | −0.0053 (5) |
N1 | 0.0373 (6) | 0.0621 (8) | 0.0423 (6) | 0.0125 (6) | −0.0161 (5) | −0.0161 (6) |
N2 | 0.0343 (6) | 0.0622 (8) | 0.0473 (7) | 0.0136 (6) | −0.0225 (5) | −0.0172 (6) |
N3 | 0.0342 (6) | 0.0498 (7) | 0.0314 (5) | −0.0114 (5) | −0.0084 (4) | −0.0014 (5) |
N4 | 0.0266 (5) | 0.0373 (6) | 0.0370 (6) | 0.0044 (4) | −0.0075 (4) | −0.0014 (5) |
C1 | 0.0260 (5) | 0.0343 (6) | 0.0290 (6) | −0.0002 (5) | −0.0067 (4) | −0.0003 (5) |
C2 | 0.0270 (5) | 0.0369 (6) | 0.0313 (6) | −0.0017 (5) | −0.0074 (4) | 0.0008 (5) |
C3 | 0.0295 (6) | 0.0378 (6) | 0.0275 (6) | −0.0080 (5) | −0.0067 (4) | 0.0015 (5) |
C4 | 0.0377 (7) | 0.0384 (7) | 0.0331 (6) | −0.0055 (5) | −0.0014 (5) | −0.0051 (5) |
C5 | 0.0328 (6) | 0.0359 (6) | 0.0387 (7) | 0.0015 (5) | −0.0020 (5) | −0.0034 (5) |
C6 | 0.0260 (5) | 0.0310 (6) | 0.0321 (6) | −0.0021 (4) | −0.0041 (4) | 0.0030 (5) |
C7 | 0.0249 (5) | 0.0417 (7) | 0.0339 (6) | 0.0061 (5) | −0.0095 (4) | −0.0011 (5) |
C8A | 0.0285 (8) | 0.0434 (10) | 0.0403 (9) | 0.0049 (8) | −0.0123 (7) | −0.0001 (8) |
C9A | 0.0304 (10) | 0.0867 (19) | 0.0443 (13) | 0.0015 (11) | −0.0041 (10) | 0.0067 (14) |
C8B | 0.021 (2) | 0.050 (3) | 0.022 (2) | 0.001 (2) | 0.0011 (19) | 0.004 (2) |
C9B | 0.025 (2) | 0.046 (3) | 0.033 (2) | 0.006 (2) | −0.0010 (18) | −0.002 (2) |
C10 | 0.0313 (6) | 0.0417 (7) | 0.0491 (8) | 0.0087 (6) | −0.0054 (6) | 0.0014 (6) |
C11 | 0.0330 (7) | 0.0664 (11) | 0.0507 (9) | 0.0147 (7) | −0.0092 (6) | 0.0017 (8) |
O1—N3 | 1.2378 (18) | C5—H5 | 0.953 (18) |
O2—N3 | 1.2431 (18) | C8A—C9A | 1.502 (3) |
N1—C7 | 1.1506 (19) | C8A—H8AB | 0.97 (2) |
N2—C2 | 1.3404 (19) | C8A—H8AA | 1.02 (2) |
N2—C8A | 1.444 (2) | C9A—H9AC | 0.97 (3) |
N2—C8B | 1.661 (7) | C9A—H9AB | 0.95 (3) |
N2—H2N | 0.89 (2) | C9A—H9AA | 1.01 (3) |
N3—C3 | 1.4311 (18) | C8B—C9B | 1.518 (8) |
N4—C6 | 1.3504 (18) | C8B—H8BA | 0.9900 |
N4—C10 | 1.4664 (19) | C8B—H8BB | 0.9900 |
N4—H4N | 0.873 (18) | C9B—H9BA | 0.9800 |
C1—C6 | 1.4230 (19) | C9B—H9BB | 0.9800 |
C1—C7 | 1.426 (2) | C9B—H9BC | 0.9800 |
C1—C2 | 1.4357 (18) | C10—C11 | 1.507 (2) |
C2—C3 | 1.433 (2) | C10—H10A | 1.055 (19) |
C3—C4 | 1.395 (2) | C10—H10B | 0.981 (19) |
C4—C5 | 1.366 (2) | C11—H11A | 0.98 (2) |
C4—H4 | 0.944 (18) | C11—H11B | 1.00 (2) |
C5—C6 | 1.416 (2) | C11—H11C | 0.95 (2) |
C2—N2—C8A | 130.67 (13) | N2—C8A—H8AA | 106.1 (13) |
C2—N2—C8B | 118.0 (2) | C9A—C8A—H8AA | 111.7 (12) |
C2—N2—H2N | 113.4 (14) | H8AB—C8A—H8AA | 105.9 (18) |
C8A—N2—H2N | 115.9 (14) | C8A—C9A—H9AC | 112.1 (15) |
C8B—N2—H2N | 109.3 (14) | C8A—C9A—H9AB | 110.5 (15) |
O1—N3—O2 | 120.68 (12) | H9AC—C9A—H9AB | 107 (2) |
O1—N3—C3 | 119.01 (13) | C8A—C9A—H9AA | 106.8 (18) |
O2—N3—C3 | 120.31 (12) | H9AC—C9A—H9AA | 109 (2) |
C6—N4—C10 | 122.29 (12) | H9AB—C9A—H9AA | 111 (2) |
C6—N4—H4N | 119.5 (11) | C9B—C8B—N2 | 103.3 (4) |
C10—N4—H4N | 117.7 (11) | C9B—C8B—H8BA | 111.1 |
C6—C1—C7 | 114.83 (11) | N2—C8B—H8BA | 111.1 |
C6—C1—C2 | 122.64 (12) | C9B—C8B—H8BB | 111.1 |
C7—C1—C2 | 122.50 (12) | N2—C8B—H8BB | 111.1 |
N2—C2—C3 | 121.03 (12) | H8BA—C8B—H8BB | 109.1 |
N2—C2—C1 | 123.66 (12) | C8B—C9B—H9BA | 109.5 |
C3—C2—C1 | 115.30 (12) | C8B—C9B—H9BB | 109.5 |
C4—C3—N3 | 116.03 (12) | H9BA—C9B—H9BB | 109.5 |
C4—C3—C2 | 121.19 (12) | C8B—C9B—H9BC | 109.5 |
N3—C3—C2 | 122.74 (12) | H9BA—C9B—H9BC | 109.5 |
C5—C4—C3 | 122.68 (13) | H9BB—C9B—H9BC | 109.5 |
C5—C4—H4 | 119.6 (11) | N4—C10—C11 | 111.24 (14) |
C3—C4—H4 | 117.7 (11) | N4—C10—H10A | 109.6 (10) |
C4—C5—C6 | 119.51 (13) | C11—C10—H10A | 107.2 (10) |
C4—C5—H5 | 120.5 (11) | N4—C10—H10B | 107.8 (10) |
C6—C5—H5 | 120.0 (11) | C11—C10—H10B | 111.3 (11) |
N4—C6—C5 | 120.04 (12) | H10A—C10—H10B | 109.7 (15) |
N4—C6—C1 | 121.32 (12) | C10—C11—H11A | 109.6 (12) |
C5—C6—C1 | 118.63 (12) | C10—C11—H11B | 109.6 (12) |
N1—C7—C1 | 173.47 (13) | H11A—C11—H11B | 106.0 (16) |
N2—C8A—C9A | 108.8 (2) | C10—C11—H11C | 111.3 (14) |
N2—C8A—H8AB | 112.5 (13) | H11A—C11—H11C | 113.0 (18) |
C9A—C8A—H8AB | 111.8 (13) | H11B—C11—H11C | 107.1 (18) |
C1—C2—C3—C4 | 1.67 (18) | C3—C2—N2—C8A | −178.77 (16) |
C2—C3—C4—C5 | −1.8 (2) | C1—C2—N2—C8B | −46.6 (3) |
C3—C4—C5—C6 | 0.1 (2) | C3—C2—N2—C8B | 134.6 (2) |
C4—C5—C6—C1 | 1.64 (19) | C2—N2—C8A—C9A | −85.4 (2) |
C5—C6—C1—C2 | −1.73 (19) | C2—N2—C8B—C9B | 129.2 (3) |
C6—C1—C2—C3 | 0.09 (18) | C2—C3—N3—O1 | −177.59 (12) |
C5—C6—N4—C10 | −1.47 (19) | C2—C3—N3—O2 | 3.01 (19) |
C1—C6—N4—C10 | 179.79 (12) | C4—C3—N3—O1 | 0.14 (18) |
C1—C2—N2—C8A | −0.1 (3) | C4—C3—N3—O2 | −179.26 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2 | 0.89 (2) | 1.88 (2) | 2.610 (2) | 138.8 (19) |
N2—H2N···O2i | 0.89 (2) | 2.47 (2) | 3.123 (2) | 130.7 (17) |
N4—H4N···N1ii | 0.873 (18) | 2.361 (19) | 3.198 (3) | 160.7 (15) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |
C16H18N4O6S | F(000) = 824 |
Mr = 394.40 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/c | Melting point: 574 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.514 (5) Å | Cell parameters from 874 reflections |
b = 8.573 (4) Å | θ = 2–56° |
c = 15.012 (5) Å | µ = 0.22 mm−1 |
β = 115.647 (12)° | T = 210 K |
V = 1799.8 (11) Å3 | Trapezoid, yellow-orange |
Z = 4 | 0.20 × 0.15 × 0.09 mm |
Bruker SMART 6000 CCD area-detector diffractometer | 3539 independent reflections |
Radiation source: sealed tube | 3011 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 26.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→18 |
Tmin = 0.793, Tmax = 1.000 | k = −10→10 |
14699 measured reflections | l = −14→18 |
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)] = 0.034 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.095 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0544P)2 + 0.4673P] where P = (Fo2 + 2Fc2)/3 |
3539 reflections | (Δ/σ)max = 0.001 |
316 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.30295 (3) | 0.20618 (4) | 0.06821 (3) | 0.03319 (13) | |
N1 | 0.29145 (11) | 0.59772 (17) | 0.38929 (10) | 0.0390 (3) | |
H1N | 0.2385 (14) | 0.596 (2) | 0.3929 (14) | 0.044 (5)* | |
N2 | 0.11761 (10) | 0.4433 (2) | 0.24413 (11) | 0.0453 (4) | |
N3 | 0.18583 (10) | 0.59468 (18) | −0.29296 (10) | 0.0410 (3) | |
H3N | 0.2287 (16) | 0.620 (3) | −0.3126 (16) | 0.059 (6)* | |
N4 | 0.38853 (9) | 0.51205 (16) | −0.17556 (9) | 0.0346 (3) | |
O1 | 0.40029 (8) | 0.15725 (14) | 0.09813 (9) | 0.0430 (3) | |
O2 | 0.22787 (9) | 0.09193 (13) | 0.04533 (9) | 0.0442 (3) | |
O3 | 0.10816 (9) | 0.52119 (19) | 0.30876 (10) | 0.0619 (4) | |
O4 | 0.04976 (9) | 0.3747 (2) | 0.18008 (12) | 0.0781 (5) | |
O5 | 0.47038 (8) | 0.47050 (18) | −0.12189 (10) | 0.0577 (4) | |
O6 | 0.37070 (9) | 0.59833 (17) | −0.24709 (9) | 0.0532 (4) | |
C1 | 0.29244 (11) | 0.51239 (18) | 0.31485 (11) | 0.0317 (3) | |
C2 | 0.21037 (10) | 0.43338 (19) | 0.24358 (11) | 0.0332 (3) | |
C3 | 0.21516 (11) | 0.34098 (19) | 0.16978 (11) | 0.0325 (3) | |
H3 | 0.1610 (14) | 0.284 (2) | 0.1257 (14) | 0.043 (5)* | |
C4 | 0.29997 (11) | 0.32660 (17) | 0.16185 (11) | 0.0305 (3) | |
C5 | 0.38194 (11) | 0.40640 (19) | 0.22851 (12) | 0.0344 (3) | |
H5 | 0.4389 (13) | 0.398 (2) | 0.2239 (13) | 0.038 (5)* | |
C6 | 0.37794 (11) | 0.4952 (2) | 0.30230 (12) | 0.0350 (4) | |
H6 | 0.4296 (14) | 0.549 (2) | 0.3446 (14) | 0.044 (5)* | |
C7 | 0.21493 (10) | 0.50875 (18) | −0.21056 (11) | 0.0319 (3) | |
C8 | 0.31179 (10) | 0.46316 (18) | −0.15161 (10) | 0.0290 (3) | |
C9 | 0.33818 (10) | 0.37282 (18) | −0.06701 (11) | 0.0293 (3) | |
H9 | 0.4028 (12) | 0.3462 (19) | −0.0309 (12) | 0.033 (4)* | |
C10 | 0.26990 (10) | 0.32403 (17) | −0.03760 (11) | 0.0302 (3) | |
C11 | 0.17391 (12) | 0.3671 (2) | −0.09329 (13) | 0.0400 (4) | |
H11 | 0.1261 (14) | 0.335 (2) | −0.0746 (14) | 0.052 (5)* | |
C12 | 0.14766 (12) | 0.4560 (2) | −0.17612 (13) | 0.0407 (4) | |
H12 | 0.0869 (14) | 0.479 (2) | −0.2090 (14) | 0.047 (5)* | |
C13 | 0.37502 (14) | 0.6672 (2) | 0.46937 (13) | 0.0416 (4) | |
H13B | 0.4216 (13) | 0.587 (2) | 0.5024 (14) | 0.044 (5)* | |
H13A | 0.4048 (13) | 0.744 (2) | 0.4420 (13) | 0.043 (5)* | |
C14 | 0.34374 (19) | 0.7486 (2) | 0.53982 (15) | 0.0531 (5) | |
H14C | 0.3119 (16) | 0.675 (3) | 0.5645 (15) | 0.062 (6)* | |
H14B | 0.3977 (18) | 0.794 (3) | 0.5913 (18) | 0.070 (7)* | |
H14A | 0.2986 (17) | 0.833 (3) | 0.5068 (18) | 0.069 (7)* | |
C15 | 0.08615 (14) | 0.6323 (3) | −0.35703 (15) | 0.0548 (5) | |
H15B | 0.0640 (16) | 0.700 (3) | −0.3184 (17) | 0.068 (7)* | |
H15A | 0.0491 (16) | 0.533 (3) | −0.3785 (17) | 0.062 (6)* | |
C16 | 0.0803 (2) | 0.7242 (4) | −0.44532 (18) | 0.0707 (7) | |
H16C | 0.105 (2) | 0.668 (3) | −0.483 (2) | 0.089 (9)* | |
H16B | 0.014 (2) | 0.748 (3) | −0.485 (2) | 0.102 (9)* | |
H16A | 0.123 (3) | 0.824 (4) | −0.422 (3) | 0.144 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0386 (2) | 0.0292 (2) | 0.0389 (2) | 0.00409 (15) | 0.02355 (18) | 0.00262 (15) |
N1 | 0.0373 (7) | 0.0475 (9) | 0.0338 (7) | −0.0001 (6) | 0.0168 (6) | −0.0026 (6) |
N2 | 0.0285 (7) | 0.0683 (10) | 0.0399 (8) | 0.0056 (7) | 0.0154 (6) | −0.0066 (7) |
N3 | 0.0351 (7) | 0.0562 (9) | 0.0323 (7) | 0.0053 (7) | 0.0152 (6) | 0.0044 (6) |
N4 | 0.0308 (7) | 0.0454 (8) | 0.0316 (7) | −0.0040 (6) | 0.0171 (6) | −0.0046 (6) |
O1 | 0.0462 (7) | 0.0407 (6) | 0.0497 (7) | 0.0155 (5) | 0.0278 (6) | 0.0075 (5) |
O2 | 0.0573 (7) | 0.0324 (6) | 0.0534 (7) | −0.0065 (5) | 0.0338 (6) | −0.0016 (5) |
O3 | 0.0391 (7) | 0.0995 (11) | 0.0530 (8) | 0.0036 (7) | 0.0256 (6) | −0.0246 (8) |
O4 | 0.0278 (7) | 0.1314 (15) | 0.0728 (10) | −0.0091 (8) | 0.0197 (7) | −0.0473 (10) |
O5 | 0.0291 (6) | 0.0890 (11) | 0.0588 (8) | 0.0043 (6) | 0.0228 (6) | 0.0208 (7) |
O6 | 0.0452 (7) | 0.0792 (10) | 0.0403 (7) | −0.0041 (6) | 0.0233 (6) | 0.0165 (6) |
C1 | 0.0332 (8) | 0.0332 (8) | 0.0295 (7) | 0.0031 (6) | 0.0144 (6) | 0.0058 (6) |
C2 | 0.0261 (7) | 0.0432 (9) | 0.0315 (8) | 0.0050 (6) | 0.0136 (6) | 0.0034 (7) |
C3 | 0.0283 (7) | 0.0376 (8) | 0.0314 (8) | 0.0015 (7) | 0.0127 (6) | 0.0010 (7) |
C4 | 0.0336 (8) | 0.0307 (8) | 0.0322 (8) | 0.0036 (6) | 0.0190 (6) | 0.0050 (6) |
C5 | 0.0293 (7) | 0.0402 (9) | 0.0400 (8) | 0.0006 (6) | 0.0209 (7) | 0.0066 (7) |
C6 | 0.0306 (8) | 0.0392 (9) | 0.0357 (8) | −0.0054 (7) | 0.0148 (7) | 0.0029 (7) |
C7 | 0.0308 (8) | 0.0370 (8) | 0.0293 (7) | 0.0016 (6) | 0.0142 (6) | −0.0044 (6) |
C8 | 0.0265 (7) | 0.0359 (8) | 0.0287 (7) | −0.0029 (6) | 0.0158 (6) | −0.0070 (6) |
C9 | 0.0259 (7) | 0.0323 (8) | 0.0308 (7) | 0.0004 (6) | 0.0134 (6) | −0.0056 (6) |
C10 | 0.0324 (7) | 0.0306 (8) | 0.0325 (8) | 0.0011 (6) | 0.0186 (6) | −0.0012 (6) |
C11 | 0.0318 (8) | 0.0511 (10) | 0.0452 (9) | 0.0001 (7) | 0.0242 (7) | 0.0022 (8) |
C12 | 0.0261 (8) | 0.0558 (11) | 0.0414 (9) | 0.0059 (7) | 0.0157 (7) | 0.0027 (8) |
C13 | 0.0501 (10) | 0.0360 (9) | 0.0364 (9) | −0.0097 (8) | 0.0165 (8) | 0.0021 (7) |
C14 | 0.0823 (15) | 0.0411 (11) | 0.0419 (10) | −0.0220 (11) | 0.0326 (11) | −0.0081 (9) |
C15 | 0.0410 (10) | 0.0757 (15) | 0.0431 (10) | 0.0170 (10) | 0.0137 (8) | 0.0103 (10) |
C16 | 0.0637 (14) | 0.095 (2) | 0.0467 (12) | 0.0296 (15) | 0.0178 (11) | 0.0231 (13) |
S1—O1 | 1.4390 (13) | C5—H5 | 0.919 (18) |
S1—O2 | 1.4449 (13) | C6—H6 | 0.90 (2) |
S1—C4 | 1.7608 (16) | C7—C12 | 1.424 (2) |
S1—C10 | 1.7612 (16) | C7—C8 | 1.429 (2) |
N1—C1 | 1.341 (2) | C8—C9 | 1.389 (2) |
N1—C13 | 1.460 (2) | C9—C10 | 1.377 (2) |
N1—H1N | 0.846 (19) | C9—H9 | 0.938 (17) |
N2—O4 | 1.226 (2) | C10—C11 | 1.405 (2) |
N2—O3 | 1.2375 (19) | C11—C12 | 1.361 (2) |
N2—C2 | 1.4451 (19) | C11—H11 | 0.94 (2) |
N3—C7 | 1.339 (2) | C12—H12 | 0.88 (2) |
N3—C15 | 1.460 (2) | C13—C14 | 1.512 (3) |
N3—H3N | 0.86 (2) | C13—H13B | 0.966 (19) |
N4—O5 | 1.2259 (18) | C13—H13A | 0.992 (19) |
N4—O6 | 1.2327 (18) | C14—H14C | 0.97 (2) |
N4—C8 | 1.4466 (18) | C14—H14B | 0.94 (3) |
C1—C6 | 1.426 (2) | C14—H14A | 0.98 (2) |
C1—C2 | 1.430 (2) | C15—C16 | 1.511 (3) |
C2—C3 | 1.390 (2) | C15—H15B | 0.98 (2) |
C3—C4 | 1.377 (2) | C15—H15A | 1.00 (2) |
C3—H3 | 0.95 (2) | C16—H16C | 0.94 (3) |
C4—C5 | 1.409 (2) | C16—H16B | 0.96 (3) |
C5—C6 | 1.367 (2) | C16—H16A | 1.05 (4) |
O1—S1—O2 | 120.38 (8) | C9—C8—C7 | 122.23 (13) |
O1—S1—C4 | 107.96 (7) | C9—C8—N4 | 116.11 (13) |
O2—S1—C4 | 106.87 (7) | C7—C8—N4 | 121.65 (13) |
O1—S1—C10 | 107.77 (7) | C10—C9—C8 | 119.94 (14) |
O2—S1—C10 | 106.52 (8) | C10—C9—H9 | 121.2 (10) |
C4—S1—C10 | 106.60 (8) | C8—C9—H9 | 118.8 (10) |
C1—N1—C13 | 125.61 (15) | C9—C10—C11 | 119.57 (14) |
C1—N1—H1N | 114.0 (13) | C9—C10—S1 | 119.95 (12) |
C13—N1—H1N | 119.6 (13) | C11—C10—S1 | 120.48 (11) |
O4—N2—O3 | 121.39 (14) | C12—C11—C10 | 120.76 (14) |
O4—N2—C2 | 119.10 (14) | C12—C11—H11 | 118.2 (12) |
O3—N2—C2 | 119.51 (14) | C10—C11—H11 | 121.0 (12) |
C7—N3—C15 | 124.57 (15) | C11—C12—C7 | 122.19 (15) |
C7—N3—H3N | 116.8 (15) | C11—C12—H12 | 117.6 (12) |
C15—N3—H3N | 118.2 (15) | C7—C12—H12 | 120.2 (13) |
O5—N4—O6 | 121.66 (13) | N1—C13—C14 | 108.96 (16) |
O5—N4—C8 | 118.83 (13) | N1—C13—H13B | 109.4 (11) |
O6—N4—C8 | 119.46 (13) | C14—C13—H13B | 111.5 (11) |
N1—C1—C6 | 120.87 (15) | N1—C13—H13A | 109.7 (11) |
N1—C1—C2 | 123.65 (14) | C14—C13—H13A | 109.2 (11) |
C6—C1—C2 | 115.48 (14) | H13B—C13—H13A | 108.0 (15) |
C3—C2—C1 | 121.92 (13) | C13—C14—H14C | 109.6 (13) |
C3—C2—N2 | 115.80 (14) | C13—C14—H14B | 108.9 (14) |
C1—C2—N2 | 122.28 (14) | H14C—C14—H14B | 112.1 (18) |
C4—C3—C2 | 120.18 (15) | C13—C14—H14A | 111.3 (14) |
C4—C3—H3 | 119.0 (11) | H14C—C14—H14A | 107.9 (19) |
C2—C3—H3 | 120.8 (11) | H14B—C14—H14A | 107.1 (19) |
C3—C4—C5 | 119.84 (14) | N3—C15—C16 | 109.70 (18) |
C3—C4—S1 | 118.54 (12) | N3—C15—H15B | 106.4 (14) |
C5—C4—S1 | 121.62 (11) | C16—C15—H15B | 107.9 (13) |
C6—C5—C4 | 120.15 (14) | N3—C15—H15A | 108.7 (13) |
C6—C5—H5 | 119.3 (11) | C16—C15—H15A | 110.8 (13) |
C4—C5—H5 | 120.5 (11) | H15B—C15—H15A | 113.3 (18) |
C5—C6—C1 | 122.37 (15) | C15—C16—H16C | 112.0 (17) |
C5—C6—H6 | 121.0 (12) | C15—C16—H16B | 107.2 (18) |
C1—C6—H6 | 116.6 (12) | H16C—C16—H16B | 110 (2) |
N3—C7—C12 | 120.20 (14) | C15—C16—H16A | 110 (2) |
N3—C7—C8 | 124.48 (14) | H16C—C16—H16A | 105 (3) |
C12—C7—C8 | 115.31 (14) | H16B—C16—H16A | 113 (3) |
C7—C8—C9—C10 | 0.1 (2) | O1—S1—C4—C5 | 23.23 (15) |
C8—C9—C10—C11 | −0.4 (2) | O1—S1—C4—C3 | −156.21 (12) |
C9—C10—C11—C12 | 0.3 (3) | O2—S1—C4—C5 | 154.05 (13) |
C10—C11—C12—C7 | 0.2 (3) | O2—S1—C4—C3 | −25.39 (14) |
C11—C12—C7—C8 | −0.6 (2) | C1—C2—C3—C4 | −1.8 (2) |
C12—C7—C8—C9 | 0.4 (2) | C2—C3—C4—C5 | −0.3 (2) |
C16—C15—N3—C7 | −177.21 (19) | C3—C4—C5—C6 | 1.4 (2) |
C15—N3—C7—C8 | 175.54 (17) | C4—C5—C6—C1 | −0.5 (2) |
C15—N3—C7—C12 | −4.4 (3) | C5—C6—C1—C2 | −1.4 (2) |
O5—N4—C8—C9 | 0.9 (2) | C6—C1—C2—C3 | 2.6 (2) |
O6—N4—C8—C9 | −176.72 (14) | C14—C13—N1—C1 | −177.91 (16) |
O5—N4—C8—C7 | 179.40 (15) | C13—N1—C1—C2 | 173.40 (16) |
O6—N4—C8—C7 | 1.8 (2) | C13—N1—C1—C6 | −6.6 (2) |
O1—S1—C10—C9 | −9.97 (15) | O3—N2—C2—C1 | −0.8 (3) |
O1—S1—C10—C11 | 169.15 (13) | O4—N2—C2—C1 | 178.90 (17) |
O2—S1—C10—C9 | −140.44 (12) | O3—N2—C2—C3 | 178.70 (16) |
O2—S1—C10—C11 | 38.68 (15) | O4—N2—C2—C3 | −1.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.846 (19) | 1.972 (19) | 2.646 (2) | 135.9 (17) |
N3—H3N···O6 | 0.86 (2) | 2.00 (2) | 2.644 (2) | 131.2 (19) |
N1—H1N···O2i | 0.846 (19) | 2.862 (19) | 3.332 (2) | 117.0 (15) |
N3—H3N···O2ii | 0.86 (2) | 2.80 (2) | 3.201 (2) | 110.4 (17) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
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