Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615012450/uk3114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012450/uk3114IVsup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114Isup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114IIsup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114IIIsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012450/uk3114IVsup9.cml |
CCDC references: 1409419; 1409418; 1409417; 1409416
For all compounds, data collection: CrystalClear (Rigaku, 2012); cell refinement: CrystalClear (Rigaku, 2012); data reduction: CrystalClear (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).
C12H13N3O3 | F(000) = 1040 |
Mr = 247.26 | Dx = 1.427 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8881 (9) Å | Cell parameters from 10133 reflections |
b = 14.0296 (17) Å | θ = 3.1–27.6° |
c = 20.810 (3) Å | µ = 0.11 mm−1 |
β = 91.749 (7)° | T = 100 K |
V = 2301.9 (5) Å3 | Chip, colourless |
Z = 8 | 0.07 × 0.04 × 0.02 mm |
Rugaku CCD diffractometer | 2385 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.108 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→6 |
21153 measured reflections | k = −18→18 |
5267 independent reflections | l = −25→26 |
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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3 |
5267 reflections | (Δ/σ)max < 0.001 |
333 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.30 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 | ||
C1 | 0.9028 (4) | 0.6339 (2) | 0.42060 (16) | 0.0292 (8) | |
H1 | 0.9550 | 0.6078 | 0.3840 | 0.035* | |
C2 | 0.8429 (4) | 0.5745 (2) | 0.46741 (16) | 0.0319 (8) | |
H2 | 0.8546 | 0.5075 | 0.4629 | 0.038* | |
C3 | 0.7665 (4) | 0.6107 (2) | 0.52070 (16) | 0.0335 (8) | |
H3 | 0.7248 | 0.5689 | 0.5525 | 0.040* | |
C4 | 0.7506 (4) | 0.7085 (2) | 0.52782 (16) | 0.0320 (8) | |
H4 | 0.6988 | 0.7341 | 0.5647 | 0.038* | |
C5 | 0.8106 (4) | 0.7688 (2) | 0.48105 (15) | 0.0286 (8) | |
H5 | 0.7996 | 0.8358 | 0.4860 | 0.034* | |
C6 | 0.8867 (4) | 0.7324 (2) | 0.42700 (15) | 0.0247 (7) | |
C7 | 0.9506 (4) | 0.7979 (2) | 0.37904 (15) | 0.0269 (7) | |
H7 | 0.9418 | 0.8647 | 0.3857 | 0.032* | |
C8 | 1.0827 (5) | 0.93197 (19) | 0.29462 (16) | 0.0337 (8) | |
H8A | 0.9654 | 0.9547 | 0.2961 | 0.051* | |
H8B | 1.1397 | 0.9633 | 0.2591 | 0.051* | |
H8C | 1.1426 | 0.9471 | 0.3353 | 0.051* | |
C9 | 1.1566 (4) | 0.7896 (2) | 0.23345 (15) | 0.0256 (7) | |
C10 | 1.1489 (4) | 0.6811 (2) | 0.23093 (15) | 0.0267 (7) | |
H10 | 1.1988 | 0.6531 | 0.2715 | 0.032* | |
C11 | 0.9681 (4) | 0.6431 (2) | 0.21806 (15) | 0.0300 (8) | |
H11A | 0.9379 | 0.5959 | 0.2512 | 0.036* | |
H11B | 0.8847 | 0.6958 | 0.2184 | 0.036* | |
C12 | 1.1301 (5) | 0.5990 (2) | 0.13464 (16) | 0.0312 (8) | |
N1 | 1.0180 (3) | 0.76675 (16) | 0.32839 (12) | 0.0256 (6) | |
N2 | 1.0833 (3) | 0.82943 (16) | 0.28472 (12) | 0.0255 (6) | |
N3 | 1.2335 (4) | 0.64422 (18) | 0.17600 (13) | 0.0315 (7) | |
H1N | 1.344 (5) | 0.654 (2) | 0.1622 (16) | 0.038* | |
O1 | 1.2231 (3) | 0.83676 (14) | 0.19142 (10) | 0.0312 (5) | |
O2 | 0.9705 (3) | 0.59923 (15) | 0.15560 (10) | 0.0357 (6) | |
O3 | 1.1654 (3) | 0.56158 (15) | 0.08375 (11) | 0.0419 (6) | |
C13 | 0.8928 (4) | 0.8429 (2) | −0.09588 (15) | 0.0293 (8) | |
H13 | 0.8325 | 0.8698 | −0.0615 | 0.035* | |
C14 | 0.9609 (4) | 0.9015 (2) | −0.14116 (15) | 0.0306 (8) | |
H14 | 0.9493 | 0.9687 | −0.1374 | 0.037* | |
C15 | 1.0457 (4) | 0.8637 (2) | −0.19184 (16) | 0.0316 (8) | |
H15 | 1.0940 | 0.9047 | −0.2227 | 0.038* | |
C16 | 1.0608 (4) | 0.7661 (2) | −0.19794 (16) | 0.0324 (8) | |
H16 | 1.1170 | 0.7399 | −0.2336 | 0.039* | |
C17 | 0.9946 (4) | 0.7066 (2) | −0.15245 (14) | 0.0279 (8) | |
H17 | 1.0058 | 0.6395 | −0.1568 | 0.033* | |
C18 | 0.9110 (4) | 0.7443 (2) | −0.09986 (14) | 0.0256 (7) | |
C19 | 0.8448 (4) | 0.6804 (2) | −0.05104 (14) | 0.0246 (7) | |
H19 | 0.8516 | 0.6132 | −0.0560 | 0.029* | |
C20 | 0.7170 (5) | 0.5545 (2) | 0.03913 (16) | 0.0350 (8) | |
H20A | 0.8351 | 0.5333 | 0.0369 | 0.052* | |
H20B | 0.6537 | 0.5341 | 0.0003 | 0.052* | |
H20C | 0.6656 | 0.5265 | 0.0770 | 0.052* | |
C21 | 0.6424 (4) | 0.7036 (2) | 0.09435 (15) | 0.0262 (7) | |
C22 | 0.6542 (4) | 0.8120 (2) | 0.09171 (15) | 0.0261 (7) | |
H22 | 0.6048 | 0.8363 | 0.0500 | 0.031* | |
C23 | 0.8370 (4) | 0.8482 (2) | 0.10210 (15) | 0.0301 (8) | |
H23A | 0.9183 | 0.7944 | 0.1024 | 0.036* | |
H23B | 0.8670 | 0.8933 | 0.0676 | 0.036* | |
C24 | 0.6797 (5) | 0.9008 (2) | 0.18577 (17) | 0.0317 (8) | |
N4 | 0.7782 (3) | 0.71670 (17) | −0.00197 (12) | 0.0260 (6) | |
N5 | 0.7120 (3) | 0.65802 (16) | 0.04380 (12) | 0.0276 (6) | |
N6 | 0.5719 (4) | 0.85637 (18) | 0.14523 (14) | 0.0314 (7) | |
H2N | 0.466 (5) | 0.857 (2) | 0.1542 (16) | 0.038* | |
O4 | 0.5786 (3) | 0.66074 (14) | 0.13891 (11) | 0.0325 (6) | |
O5 | 0.8399 (3) | 0.89520 (14) | 0.16334 (10) | 0.0335 (6) | |
O6 | 0.6516 (3) | 0.94059 (15) | 0.23570 (11) | 0.0417 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0306 (19) | 0.0274 (16) | 0.0297 (18) | 0.0008 (14) | 0.0017 (15) | −0.0016 (14) |
C2 | 0.038 (2) | 0.0218 (15) | 0.036 (2) | −0.0033 (14) | −0.0052 (16) | −0.0005 (14) |
C3 | 0.036 (2) | 0.0362 (18) | 0.0277 (18) | −0.0107 (16) | −0.0011 (16) | 0.0071 (15) |
C4 | 0.032 (2) | 0.0346 (18) | 0.0293 (18) | −0.0034 (15) | 0.0027 (16) | −0.0018 (15) |
C5 | 0.0292 (19) | 0.0264 (16) | 0.0300 (18) | −0.0002 (14) | −0.0021 (15) | −0.0031 (14) |
C6 | 0.0234 (17) | 0.0233 (15) | 0.0274 (18) | −0.0019 (13) | 0.0011 (14) | 0.0006 (13) |
C7 | 0.0314 (19) | 0.0219 (15) | 0.0273 (18) | −0.0009 (13) | −0.0009 (16) | −0.0028 (13) |
C8 | 0.051 (2) | 0.0144 (14) | 0.0363 (19) | −0.0035 (15) | 0.0045 (17) | −0.0015 (13) |
C9 | 0.0261 (19) | 0.0208 (14) | 0.0299 (18) | −0.0020 (13) | −0.0008 (15) | 0.0026 (14) |
C10 | 0.0319 (19) | 0.0216 (15) | 0.0268 (18) | 0.0014 (13) | 0.0052 (15) | 0.0022 (13) |
C11 | 0.039 (2) | 0.0224 (15) | 0.0291 (19) | −0.0035 (14) | 0.0037 (16) | −0.0034 (13) |
C12 | 0.042 (2) | 0.0213 (15) | 0.0309 (19) | 0.0035 (15) | 0.0060 (17) | 0.0034 (15) |
N1 | 0.0300 (16) | 0.0215 (12) | 0.0252 (15) | −0.0025 (11) | 0.0010 (13) | 0.0032 (11) |
N2 | 0.0331 (16) | 0.0177 (12) | 0.0257 (15) | 0.0000 (11) | 0.0028 (12) | 0.0001 (11) |
N3 | 0.0332 (17) | 0.0250 (14) | 0.0367 (17) | 0.0005 (13) | 0.0076 (14) | −0.0024 (12) |
O1 | 0.0328 (14) | 0.0255 (11) | 0.0354 (13) | −0.0018 (10) | 0.0047 (11) | 0.0039 (10) |
O2 | 0.0393 (16) | 0.0319 (12) | 0.0358 (13) | −0.0043 (11) | 0.0005 (12) | −0.0061 (10) |
O3 | 0.0607 (18) | 0.0304 (12) | 0.0350 (14) | 0.0019 (12) | 0.0060 (13) | −0.0066 (11) |
C13 | 0.0328 (19) | 0.0284 (16) | 0.0268 (18) | −0.0026 (15) | 0.0033 (15) | −0.0051 (14) |
C14 | 0.035 (2) | 0.0263 (15) | 0.0309 (18) | −0.0053 (15) | 0.0002 (16) | 0.0018 (14) |
C15 | 0.030 (2) | 0.0340 (17) | 0.0306 (19) | −0.0055 (15) | 0.0004 (16) | 0.0035 (15) |
C16 | 0.036 (2) | 0.0321 (17) | 0.0292 (19) | −0.0022 (16) | 0.0035 (16) | −0.0021 (15) |
C17 | 0.0260 (19) | 0.0272 (16) | 0.0303 (19) | −0.0030 (14) | 0.0002 (15) | −0.0020 (14) |
C18 | 0.0249 (17) | 0.0241 (15) | 0.0277 (18) | −0.0030 (13) | −0.0011 (15) | −0.0038 (13) |
C19 | 0.0245 (18) | 0.0236 (15) | 0.0255 (17) | −0.0021 (13) | −0.0018 (14) | −0.0032 (13) |
C20 | 0.051 (2) | 0.0202 (15) | 0.034 (2) | −0.0038 (15) | 0.0058 (17) | −0.0023 (14) |
C21 | 0.0229 (18) | 0.0264 (15) | 0.0293 (18) | −0.0011 (13) | 0.0024 (15) | 0.0027 (14) |
C22 | 0.033 (2) | 0.0208 (14) | 0.0251 (17) | 0.0043 (14) | 0.0026 (15) | 0.0000 (13) |
C23 | 0.0317 (19) | 0.0243 (15) | 0.034 (2) | 0.0014 (14) | −0.0016 (16) | 0.0012 (14) |
C24 | 0.043 (2) | 0.0176 (14) | 0.035 (2) | −0.0007 (15) | 0.0025 (17) | 0.0017 (14) |
N4 | 0.0259 (15) | 0.0250 (13) | 0.0273 (15) | −0.0053 (11) | 0.0028 (12) | 0.0026 (12) |
N5 | 0.0344 (16) | 0.0202 (12) | 0.0285 (15) | −0.0015 (12) | 0.0035 (13) | 0.0010 (11) |
N6 | 0.0332 (17) | 0.0295 (14) | 0.0319 (16) | 0.0019 (14) | 0.0054 (14) | −0.0054 (12) |
O4 | 0.0345 (14) | 0.0275 (11) | 0.0358 (13) | −0.0017 (10) | 0.0071 (11) | 0.0047 (10) |
O5 | 0.0361 (15) | 0.0259 (11) | 0.0386 (14) | −0.0058 (10) | 0.0012 (11) | −0.0072 (10) |
O6 | 0.0583 (17) | 0.0265 (12) | 0.0405 (14) | −0.0067 (11) | 0.0082 (13) | −0.0122 (11) |
C1—C2 | 1.376 (4) | C13—C14 | 1.373 (4) |
C1—C6 | 1.395 (4) | C13—C18 | 1.393 (4) |
C1—H1 | 0.9500 | C13—H13 | 0.9500 |
C2—C3 | 1.376 (5) | C14—C15 | 1.373 (5) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.386 (4) | C15—C16 | 1.381 (4) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.383 (4) | C16—C17 | 1.377 (4) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.388 (4) | C17—C18 | 1.398 (4) |
C5—H5 | 0.9500 | C17—H17 | 0.9500 |
C6—C7 | 1.458 (4) | C18—C19 | 1.463 (4) |
C7—N1 | 1.272 (4) | C19—N4 | 1.269 (4) |
C7—H7 | 0.9500 | C19—H19 | 0.9500 |
C8—N2 | 1.453 (3) | C20—N5 | 1.456 (4) |
C8—H8A | 0.9800 | C20—H20A | 0.9800 |
C8—H8B | 0.9800 | C20—H20B | 0.9800 |
C8—H8C | 0.9800 | C20—H20C | 0.9800 |
C9—O1 | 1.228 (4) | C21—O4 | 1.226 (4) |
C9—N2 | 1.350 (4) | C21—N5 | 1.361 (4) |
C9—C10 | 1.523 (4) | C21—C22 | 1.525 (4) |
C10—N3 | 1.438 (4) | C22—N6 | 1.447 (4) |
C10—C11 | 1.539 (4) | C22—C23 | 1.538 (5) |
C10—H10 | 1.0000 | C22—H22 | 1.0000 |
C11—O2 | 1.439 (4) | C23—O5 | 1.434 (4) |
C11—H11A | 0.9900 | C23—H23A | 0.9900 |
C11—H11B | 0.9900 | C23—H23B | 0.9900 |
C12—O3 | 1.222 (4) | C24—O6 | 1.206 (4) |
C12—N3 | 1.329 (4) | C24—N6 | 1.334 (4) |
C12—O2 | 1.345 (4) | C24—O5 | 1.363 (4) |
N1—N2 | 1.376 (3) | N4—N5 | 1.374 (3) |
N3—H1N | 0.93 (4) | N6—H2N | 0.86 (4) |
C2—C1—C6 | 119.9 (3) | C14—C13—C18 | 120.7 (3) |
C2—C1—H1 | 120.1 | C14—C13—H13 | 119.6 |
C6—C1—H1 | 120.1 | C18—C13—H13 | 119.6 |
C3—C2—C1 | 121.0 (3) | C15—C14—C13 | 120.4 (3) |
C3—C2—H2 | 119.5 | C15—C14—H14 | 119.8 |
C1—C2—H2 | 119.5 | C13—C14—H14 | 119.8 |
C2—C3—C4 | 119.7 (3) | C14—C15—C16 | 120.0 (3) |
C2—C3—H3 | 120.2 | C14—C15—H15 | 120.0 |
C4—C3—H3 | 120.2 | C16—C15—H15 | 120.0 |
C5—C4—C3 | 119.7 (3) | C17—C16—C15 | 120.1 (3) |
C5—C4—H4 | 120.2 | C17—C16—H16 | 119.9 |
C3—C4—H4 | 120.2 | C15—C16—H16 | 119.9 |
C4—C5—C6 | 120.8 (3) | C16—C17—C18 | 120.5 (3) |
C4—C5—H5 | 119.6 | C16—C17—H17 | 119.8 |
C6—C5—H5 | 119.6 | C18—C17—H17 | 119.8 |
C5—C6—C1 | 119.0 (3) | C13—C18—C17 | 118.3 (3) |
C5—C6—C7 | 119.3 (3) | C13—C18—C19 | 121.8 (3) |
C1—C6—C7 | 121.7 (3) | C17—C18—C19 | 119.9 (3) |
N1—C7—C6 | 120.8 (3) | N4—C19—C18 | 118.5 (3) |
N1—C7—H7 | 119.6 | N4—C19—H19 | 120.7 |
C6—C7—H7 | 119.6 | C18—C19—H19 | 120.7 |
N2—C8—H8A | 109.5 | N5—C20—H20A | 109.5 |
N2—C8—H8B | 109.5 | N5—C20—H20B | 109.5 |
H8A—C8—H8B | 109.5 | H20A—C20—H20B | 109.5 |
N2—C8—H8C | 109.5 | N5—C20—H20C | 109.5 |
H8A—C8—H8C | 109.5 | H20A—C20—H20C | 109.5 |
H8B—C8—H8C | 109.5 | H20B—C20—H20C | 109.5 |
O1—C9—N2 | 122.8 (3) | O4—C21—N5 | 122.6 (3) |
O1—C9—C10 | 122.1 (3) | O4—C21—C22 | 122.9 (3) |
N2—C9—C10 | 115.0 (3) | N5—C21—C22 | 114.5 (3) |
N3—C10—C9 | 111.6 (3) | N6—C22—C21 | 111.8 (3) |
N3—C10—C11 | 100.8 (2) | N6—C22—C23 | 101.0 (2) |
C9—C10—C11 | 112.8 (3) | C21—C22—C23 | 112.5 (3) |
N3—C10—H10 | 110.4 | N6—C22—H22 | 110.4 |
C9—C10—H10 | 110.4 | C21—C22—H22 | 110.4 |
C11—C10—H10 | 110.4 | C23—C22—H22 | 110.4 |
O2—C11—C10 | 105.5 (3) | O5—C23—C22 | 105.4 (3) |
O2—C11—H11A | 110.6 | O5—C23—H23A | 110.7 |
C10—C11—H11A | 110.6 | C22—C23—H23A | 110.7 |
O2—C11—H11B | 110.6 | O5—C23—H23B | 110.7 |
C10—C11—H11B | 110.6 | C22—C23—H23B | 110.7 |
H11A—C11—H11B | 108.8 | H23A—C23—H23B | 108.8 |
O3—C12—N3 | 127.9 (3) | O6—C24—N6 | 129.1 (4) |
O3—C12—O2 | 121.5 (3) | O6—C24—O5 | 121.3 (3) |
N3—C12—O2 | 110.6 (3) | N6—C24—O5 | 109.6 (3) |
C7—N1—N2 | 120.1 (2) | C19—N4—N5 | 119.5 (2) |
C9—N2—N1 | 115.8 (2) | C21—N5—N4 | 115.2 (2) |
C9—N2—C8 | 121.7 (3) | C21—N5—C20 | 122.2 (3) |
N1—N2—C8 | 122.4 (2) | N4—N5—C20 | 122.7 (3) |
C12—N3—C10 | 113.3 (3) | C24—N6—C22 | 113.3 (3) |
C12—N3—H1N | 115 (2) | C24—N6—H2N | 118 (2) |
C10—N3—H1N | 131 (2) | C22—N6—H2N | 129 (2) |
C12—O2—C11 | 109.4 (3) | C24—O5—C23 | 110.0 (2) |
C6—C1—C2—C3 | 0.2 (5) | C18—C13—C14—C15 | 1.2 (5) |
C1—C2—C3—C4 | −0.6 (5) | C13—C14—C15—C16 | 0.9 (5) |
C2—C3—C4—C5 | 0.5 (5) | C14—C15—C16—C17 | −1.6 (5) |
C3—C4—C5—C6 | −0.1 (5) | C15—C16—C17—C18 | 0.3 (5) |
C4—C5—C6—C1 | −0.3 (5) | C14—C13—C18—C17 | −2.5 (5) |
C4—C5—C6—C7 | −179.2 (3) | C14—C13—C18—C19 | 177.8 (3) |
C2—C1—C6—C5 | 0.2 (5) | C16—C17—C18—C13 | 1.7 (5) |
C2—C1—C6—C7 | 179.1 (3) | C16—C17—C18—C19 | −178.5 (3) |
C5—C6—C7—N1 | −178.6 (3) | C13—C18—C19—N4 | −4.3 (4) |
C1—C6—C7—N1 | 2.5 (5) | C17—C18—C19—N4 | 176.0 (3) |
O1—C9—C10—N3 | 2.4 (4) | O4—C21—C22—N6 | −3.8 (4) |
N2—C9—C10—N3 | −178.4 (3) | N5—C21—C22—N6 | 177.6 (3) |
O1—C9—C10—C11 | −110.3 (3) | O4—C21—C22—C23 | 109.0 (3) |
N2—C9—C10—C11 | 68.9 (4) | N5—C21—C22—C23 | −69.6 (3) |
N3—C10—C11—O2 | −5.7 (3) | N6—C22—C23—O5 | 8.1 (3) |
C9—C10—C11—O2 | 113.4 (3) | C21—C22—C23—O5 | −111.3 (3) |
C6—C7—N1—N2 | −177.6 (3) | C18—C19—N4—N5 | 178.6 (3) |
O1—C9—N2—N1 | −178.5 (3) | O4—C21—N5—N4 | −180.0 (3) |
C10—C9—N2—N1 | 2.3 (4) | C22—C21—N5—N4 | −1.3 (4) |
O1—C9—N2—C8 | −1.9 (5) | O4—C21—N5—C20 | −0.5 (5) |
C10—C9—N2—C8 | 178.9 (3) | C22—C21—N5—C20 | 178.1 (3) |
C7—N1—N2—C9 | 178.1 (3) | C19—N4—N5—C21 | −179.6 (3) |
C7—N1—N2—C8 | 1.5 (4) | C19—N4—N5—C20 | 1.0 (4) |
O3—C12—N3—C10 | 179.1 (3) | O6—C24—N6—C22 | −176.5 (3) |
O2—C12—N3—C10 | −0.3 (4) | O5—C24—N6—C22 | 2.6 (4) |
C9—C10—N3—C12 | −116.1 (3) | C21—C22—N6—C24 | 113.1 (3) |
C11—C10—N3—C12 | 3.9 (3) | C23—C22—N6—C24 | −6.7 (3) |
O3—C12—O2—C11 | 176.7 (3) | O6—C24—O5—C23 | −177.5 (3) |
N3—C12—O2—C11 | −3.8 (3) | N6—C24—O5—C23 | 3.3 (3) |
C10—C11—O2—C12 | 6.0 (3) | C22—C23—O5—C24 | −7.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N···O4i | 0.93 (4) | 1.93 (4) | 2.861 (4) | 174 (3) |
N6—H2N···O1ii | 0.86 (4) | 2.11 (4) | 2.955 (4) | 168 (3) |
C11—H11A···O6iii | 0.99 | 2.31 | 3.154 (4) | 143 |
C14—H14···O5iv | 0.95 | 2.60 | 3.296 (4) | 130 |
C19—H19···O3v | 0.95 | 2.52 | 3.463 (4) | 171 |
C10—H10···Cg4vi | 1.00 | 2.81 | 3.587 (3) | 135 |
C22—H22···Cg2vii | 1.00 | 2.67 | 3.512 (3) | 142 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+2, −y+2, −z; (v) −x+2, −y+1, −z; (vi) x−1/2, −y+3/2, z+1/2; (vii) x−3/2, −y+3/2, z−1/2. |
C12H12ClN3O3 | F(000) = 1168 |
Mr = 281.70 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
a = 15.7925 (11) Å | Cell parameters from 38129 reflections |
b = 13.7715 (4) Å | θ = 3.2–27.6° |
c = 11.3887 (3) Å | µ = 0.32 mm−1 |
β = 94.350 (7)° | T = 100 K |
V = 2469.8 (2) Å3 | Cut needle, colourless |
Z = 8 | 0.14 × 0.05 × 0.05 mm |
Rigaku CCD diffractometer | 4918 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −20→20 |
53991 measured reflections | k = −17→17 |
5667 independent reflections | l = −14→14 |
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: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0416P)2 + 1.0893P] where P = (Fo2 + 2Fc2)/3 |
5667 reflections | (Δ/σ)max = 0.001 |
351 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.37 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 | ||
C1 | −0.08148 (9) | 0.15608 (10) | 0.75150 (12) | 0.0205 (3) | |
C2 | −0.14794 (9) | 0.21323 (11) | 0.78375 (12) | 0.0246 (3) | |
H2 | −0.1768 | 0.1974 | 0.8515 | 0.030* | |
C3 | −0.17192 (9) | 0.29331 (12) | 0.71665 (13) | 0.0268 (3) | |
H3 | −0.2177 | 0.3326 | 0.7381 | 0.032* | |
C4 | −0.12970 (10) | 0.31697 (11) | 0.61792 (13) | 0.0259 (3) | |
H4 | −0.1454 | 0.3732 | 0.5731 | 0.031* | |
C5 | −0.06473 (9) | 0.25811 (11) | 0.58545 (12) | 0.0229 (3) | |
H5 | −0.0365 | 0.2740 | 0.5172 | 0.028* | |
C6 | −0.03945 (8) | 0.17575 (10) | 0.65047 (12) | 0.0191 (3) | |
C7 | 0.02752 (9) | 0.11153 (10) | 0.61446 (12) | 0.0199 (3) | |
H7 | 0.0496 | 0.0621 | 0.6663 | 0.024* | |
C8 | 0.15138 (10) | −0.01736 (11) | 0.56425 (14) | 0.0286 (3) | |
H8A | 0.1055 | −0.0621 | 0.5806 | 0.043* | |
H8B | 0.1746 | 0.0123 | 0.6380 | 0.043* | |
H8C | 0.1964 | −0.0531 | 0.5282 | 0.043* | |
C9 | 0.15298 (8) | 0.07315 (10) | 0.37916 (12) | 0.0199 (3) | |
C10 | 0.11701 (8) | 0.15820 (10) | 0.30531 (11) | 0.0181 (3) | |
H10 | 0.0546 | 0.1497 | 0.2860 | 0.022* | |
C11 | 0.13572 (9) | 0.25819 (10) | 0.36310 (12) | 0.0197 (3) | |
H11A | 0.0826 | 0.2957 | 0.3681 | 0.024* | |
H11B | 0.1636 | 0.2504 | 0.4434 | 0.024* | |
C12 | 0.20637 (8) | 0.24831 (10) | 0.19538 (11) | 0.0191 (3) | |
N1 | 0.05645 (7) | 0.12174 (8) | 0.51339 (10) | 0.0189 (2) | |
N2 | 0.11838 (7) | 0.05800 (9) | 0.48424 (10) | 0.0212 (2) | |
N3 | 0.16061 (8) | 0.16725 (9) | 0.19918 (10) | 0.0213 (2) | |
H1N | 0.1711 (11) | 0.1198 (13) | 0.1517 (16) | 0.026* | |
O1 | 0.20897 (7) | 0.02183 (8) | 0.34666 (9) | 0.0266 (2) | |
O2 | 0.19164 (6) | 0.30651 (7) | 0.28724 (8) | 0.0223 (2) | |
O3 | 0.25463 (6) | 0.27309 (8) | 0.12262 (9) | 0.0241 (2) | |
Cl1 | −0.04998 (2) | 0.05875 (3) | 0.84234 (3) | 0.02474 (9) | |
C13 | 0.56251 (10) | 0.14917 (10) | 0.42951 (13) | 0.0250 (3) | |
C14 | 0.53076 (11) | 0.15874 (11) | 0.31362 (13) | 0.0287 (3) | |
H14 | 0.5677 | 0.1741 | 0.2542 | 0.034* | |
C15 | 0.44561 (11) | 0.14600 (11) | 0.28483 (13) | 0.0292 (3) | |
H15 | 0.4234 | 0.1517 | 0.2052 | 0.035* | |
C16 | 0.39207 (11) | 0.12482 (11) | 0.37209 (13) | 0.0288 (3) | |
H16 | 0.3330 | 0.1160 | 0.3524 | 0.035* | |
C17 | 0.42431 (10) | 0.11642 (11) | 0.48793 (12) | 0.0240 (3) | |
H17 | 0.3868 | 0.1028 | 0.5472 | 0.029* | |
C18 | 0.51063 (9) | 0.12747 (10) | 0.51929 (12) | 0.0199 (3) | |
C19 | 0.54573 (9) | 0.11580 (10) | 0.64101 (12) | 0.0197 (3) | |
H19 | 0.6053 | 0.1098 | 0.6583 | 0.024* | |
C20 | 0.62059 (9) | 0.09449 (11) | 0.86619 (13) | 0.0245 (3) | |
H20A | 0.6405 | 0.0337 | 0.8330 | 0.037* | |
H20B | 0.6322 | 0.0937 | 0.9519 | 0.037* | |
H20C | 0.6503 | 0.1494 | 0.8331 | 0.037* | |
C21 | 0.47414 (9) | 0.11161 (9) | 0.92288 (11) | 0.0183 (3) | |
C22 | 0.38093 (8) | 0.11961 (10) | 0.87722 (11) | 0.0175 (3) | |
H22 | 0.3716 | 0.1794 | 0.8281 | 0.021* | |
C23 | 0.34884 (9) | 0.02976 (11) | 0.80753 (12) | 0.0217 (3) | |
H23A | 0.3318 | 0.0472 | 0.7248 | 0.026* | |
H23B | 0.3937 | −0.0205 | 0.8083 | 0.026* | |
C24 | 0.26361 (9) | 0.05338 (10) | 0.95763 (11) | 0.0195 (3) | |
N4 | 0.49557 (7) | 0.11382 (8) | 0.72380 (9) | 0.0177 (2) | |
N5 | 0.52995 (7) | 0.10439 (8) | 0.83740 (10) | 0.0187 (2) | |
N6 | 0.32536 (7) | 0.11978 (9) | 0.97243 (10) | 0.0190 (2) | |
H2N | 0.3167 (11) | 0.1701 (13) | 1.0160 (15) | 0.023* | |
O4 | 0.49702 (7) | 0.11180 (7) | 1.02703 (8) | 0.0237 (2) | |
O5 | 0.27691 (6) | −0.00512 (7) | 0.86555 (8) | 0.0210 (2) | |
O6 | 0.20361 (7) | 0.04052 (8) | 1.01606 (9) | 0.0265 (2) | |
Cl2 | 0.67070 (3) | 0.16703 (4) | 0.46267 (4) | 0.04530 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0231 (6) | 0.0230 (7) | 0.0154 (6) | −0.0034 (5) | 0.0012 (5) | −0.0008 (5) |
C2 | 0.0236 (7) | 0.0340 (8) | 0.0170 (6) | −0.0031 (6) | 0.0061 (5) | −0.0045 (6) |
C3 | 0.0251 (7) | 0.0345 (8) | 0.0211 (7) | 0.0055 (6) | 0.0033 (6) | −0.0067 (6) |
C4 | 0.0282 (7) | 0.0290 (8) | 0.0204 (7) | 0.0076 (6) | 0.0014 (6) | −0.0001 (6) |
C5 | 0.0260 (7) | 0.0269 (7) | 0.0164 (6) | 0.0027 (6) | 0.0045 (5) | 0.0012 (5) |
C6 | 0.0197 (6) | 0.0230 (7) | 0.0147 (6) | −0.0012 (5) | 0.0018 (5) | −0.0012 (5) |
C7 | 0.0222 (6) | 0.0206 (7) | 0.0169 (6) | −0.0006 (5) | 0.0013 (5) | 0.0021 (5) |
C8 | 0.0307 (8) | 0.0293 (8) | 0.0261 (8) | 0.0121 (6) | 0.0041 (6) | 0.0088 (6) |
C9 | 0.0189 (6) | 0.0221 (7) | 0.0187 (6) | −0.0005 (5) | 0.0013 (5) | −0.0016 (5) |
C10 | 0.0197 (6) | 0.0219 (7) | 0.0132 (6) | −0.0007 (5) | 0.0040 (5) | −0.0010 (5) |
C11 | 0.0218 (6) | 0.0223 (7) | 0.0154 (6) | −0.0006 (5) | 0.0046 (5) | −0.0004 (5) |
C12 | 0.0209 (6) | 0.0227 (7) | 0.0135 (6) | 0.0000 (5) | −0.0002 (5) | −0.0007 (5) |
N1 | 0.0181 (5) | 0.0205 (6) | 0.0184 (5) | 0.0024 (4) | 0.0032 (4) | 0.0011 (4) |
N2 | 0.0213 (6) | 0.0225 (6) | 0.0203 (6) | 0.0059 (4) | 0.0051 (4) | 0.0037 (5) |
N3 | 0.0268 (6) | 0.0221 (6) | 0.0159 (6) | −0.0040 (5) | 0.0078 (5) | −0.0044 (5) |
O1 | 0.0249 (5) | 0.0291 (6) | 0.0267 (5) | 0.0071 (4) | 0.0066 (4) | −0.0015 (4) |
O2 | 0.0292 (5) | 0.0225 (5) | 0.0159 (5) | −0.0065 (4) | 0.0053 (4) | −0.0030 (4) |
O3 | 0.0270 (5) | 0.0279 (5) | 0.0182 (5) | −0.0059 (4) | 0.0063 (4) | −0.0006 (4) |
Cl1 | 0.03303 (19) | 0.02462 (18) | 0.01709 (16) | −0.00449 (14) | 0.00523 (13) | 0.00336 (12) |
C13 | 0.0289 (7) | 0.0211 (7) | 0.0266 (7) | 0.0107 (6) | 0.0120 (6) | 0.0066 (6) |
C14 | 0.0466 (9) | 0.0211 (7) | 0.0206 (7) | 0.0134 (6) | 0.0165 (6) | 0.0050 (6) |
C15 | 0.0523 (10) | 0.0204 (7) | 0.0151 (7) | 0.0051 (7) | 0.0032 (6) | 0.0006 (5) |
C16 | 0.0377 (8) | 0.0262 (8) | 0.0218 (7) | −0.0027 (6) | −0.0020 (6) | 0.0013 (6) |
C17 | 0.0306 (7) | 0.0238 (7) | 0.0182 (7) | −0.0029 (6) | 0.0049 (6) | 0.0023 (5) |
C18 | 0.0277 (7) | 0.0161 (6) | 0.0166 (6) | 0.0048 (5) | 0.0064 (5) | 0.0023 (5) |
C19 | 0.0215 (6) | 0.0178 (6) | 0.0201 (7) | 0.0016 (5) | 0.0041 (5) | 0.0027 (5) |
C20 | 0.0202 (7) | 0.0304 (8) | 0.0224 (7) | −0.0012 (6) | −0.0013 (5) | 0.0031 (6) |
C21 | 0.0245 (6) | 0.0142 (6) | 0.0160 (6) | −0.0013 (5) | 0.0006 (5) | 0.0006 (5) |
C22 | 0.0216 (6) | 0.0185 (6) | 0.0126 (6) | 0.0020 (5) | 0.0035 (5) | 0.0009 (5) |
C23 | 0.0211 (6) | 0.0266 (7) | 0.0180 (6) | −0.0025 (5) | 0.0057 (5) | −0.0056 (5) |
C24 | 0.0252 (7) | 0.0195 (6) | 0.0140 (6) | 0.0029 (5) | 0.0030 (5) | 0.0014 (5) |
N4 | 0.0217 (5) | 0.0168 (5) | 0.0144 (5) | 0.0009 (4) | 0.0006 (4) | 0.0025 (4) |
N5 | 0.0194 (5) | 0.0215 (6) | 0.0148 (5) | −0.0001 (4) | −0.0004 (4) | 0.0030 (4) |
N6 | 0.0239 (6) | 0.0193 (6) | 0.0145 (5) | 0.0003 (4) | 0.0053 (4) | −0.0024 (4) |
O4 | 0.0289 (5) | 0.0280 (5) | 0.0139 (5) | −0.0018 (4) | −0.0012 (4) | 0.0000 (4) |
O5 | 0.0249 (5) | 0.0210 (5) | 0.0179 (5) | −0.0025 (4) | 0.0069 (4) | −0.0034 (4) |
O6 | 0.0312 (5) | 0.0274 (5) | 0.0227 (5) | −0.0044 (4) | 0.0127 (4) | −0.0032 (4) |
Cl2 | 0.02391 (19) | 0.0669 (3) | 0.0474 (3) | 0.01720 (19) | 0.01757 (17) | 0.0329 (2) |
C1—C2 | 1.384 (2) | C13—C14 | 1.382 (2) |
C1—C6 | 1.3978 (18) | C13—C18 | 1.3904 (19) |
C1—Cl1 | 1.7426 (14) | C13—Cl2 | 1.7390 (16) |
C2—C3 | 1.378 (2) | C14—C15 | 1.371 (2) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.389 (2) | C15—C16 | 1.384 (2) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.380 (2) | C16—C17 | 1.382 (2) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.3962 (19) | C17—C18 | 1.391 (2) |
C5—H5 | 0.9500 | C17—H17 | 0.9500 |
C6—C7 | 1.4610 (19) | C18—C19 | 1.4623 (19) |
C7—N1 | 1.2779 (18) | C19—N4 | 1.2770 (17) |
C7—H7 | 0.9500 | C19—H19 | 0.9500 |
C8—N2 | 1.4515 (18) | C20—N5 | 1.4505 (17) |
C8—H8A | 0.9800 | C20—H20A | 0.9800 |
C8—H8B | 0.9800 | C20—H20B | 0.9800 |
C8—H8C | 0.9800 | C20—H20C | 0.9800 |
C9—O1 | 1.2116 (17) | C21—O4 | 1.2134 (16) |
C9—N2 | 1.3687 (17) | C21—N5 | 1.3656 (17) |
C9—C10 | 1.5262 (19) | C21—C22 | 1.5275 (19) |
C10—N3 | 1.4411 (17) | C22—N6 | 1.4458 (16) |
C10—C11 | 1.5450 (19) | C22—C23 | 1.5352 (18) |
C10—H10 | 1.0000 | C22—H22 | 1.0000 |
C11—O2 | 1.4439 (16) | C23—O5 | 1.4393 (16) |
C11—H11A | 0.9900 | C23—H23A | 0.9900 |
C11—H11B | 0.9900 | C23—H23B | 0.9900 |
C12—O3 | 1.2164 (16) | C24—O6 | 1.2116 (17) |
C12—N3 | 1.3324 (18) | C24—N6 | 1.3381 (18) |
C12—O2 | 1.3520 (16) | C24—O5 | 1.3514 (16) |
N1—N2 | 1.3736 (15) | N4—N5 | 1.3707 (15) |
N3—H1N | 0.873 (18) | N6—H2N | 0.869 (18) |
C2—C1—C6 | 121.70 (13) | C14—C13—C18 | 122.10 (15) |
C2—C1—Cl1 | 117.91 (11) | C14—C13—Cl2 | 118.24 (12) |
C6—C1—Cl1 | 120.38 (11) | C18—C13—Cl2 | 119.66 (12) |
C3—C2—C1 | 119.34 (13) | C15—C14—C13 | 119.63 (14) |
C3—C2—H2 | 120.3 | C15—C14—H14 | 120.2 |
C1—C2—H2 | 120.3 | C13—C14—H14 | 120.2 |
C2—C3—C4 | 120.53 (14) | C14—C15—C16 | 119.79 (14) |
C2—C3—H3 | 119.7 | C14—C15—H15 | 120.1 |
C4—C3—H3 | 119.7 | C16—C15—H15 | 120.1 |
C5—C4—C3 | 119.45 (14) | C17—C16—C15 | 120.14 (15) |
C5—C4—H4 | 120.3 | C17—C16—H16 | 119.9 |
C3—C4—H4 | 120.3 | C15—C16—H16 | 119.9 |
C4—C5—C6 | 121.57 (13) | C16—C17—C18 | 121.24 (14) |
C4—C5—H5 | 119.2 | C16—C17—H17 | 119.4 |
C6—C5—H5 | 119.2 | C18—C17—H17 | 119.4 |
C5—C6—C1 | 117.35 (13) | C13—C18—C17 | 117.10 (13) |
C5—C6—C7 | 121.79 (12) | C13—C18—C19 | 121.23 (13) |
C1—C6—C7 | 120.86 (12) | C17—C18—C19 | 121.67 (12) |
N1—C7—C6 | 120.14 (12) | N4—C19—C18 | 119.37 (12) |
N1—C7—H7 | 119.9 | N4—C19—H19 | 120.3 |
C6—C7—H7 | 119.9 | C18—C19—H19 | 120.3 |
N2—C8—H8A | 109.5 | N5—C20—H20A | 109.5 |
N2—C8—H8B | 109.5 | N5—C20—H20B | 109.5 |
H8A—C8—H8B | 109.5 | H20A—C20—H20B | 109.5 |
N2—C8—H8C | 109.5 | N5—C20—H20C | 109.5 |
H8A—C8—H8C | 109.5 | H20A—C20—H20C | 109.5 |
H8B—C8—H8C | 109.5 | H20B—C20—H20C | 109.5 |
O1—C9—N2 | 121.81 (13) | O4—C21—N5 | 122.45 (13) |
O1—C9—C10 | 121.94 (12) | O4—C21—C22 | 122.72 (12) |
N2—C9—C10 | 116.24 (11) | N5—C21—C22 | 114.83 (11) |
N3—C10—C9 | 110.30 (11) | N6—C22—C21 | 111.65 (11) |
N3—C10—C11 | 101.08 (10) | N6—C22—C23 | 101.17 (10) |
C9—C10—C11 | 113.46 (11) | C21—C22—C23 | 112.94 (11) |
N3—C10—H10 | 110.6 | N6—C22—H22 | 110.3 |
C9—C10—H10 | 110.6 | C21—C22—H22 | 110.3 |
C11—C10—H10 | 110.6 | C23—C22—H22 | 110.3 |
O2—C11—C10 | 105.17 (10) | O5—C23—C22 | 105.83 (10) |
O2—C11—H11A | 110.7 | O5—C23—H23A | 110.6 |
C10—C11—H11A | 110.7 | C22—C23—H23A | 110.6 |
O2—C11—H11B | 110.7 | O5—C23—H23B | 110.6 |
C10—C11—H11B | 110.7 | C22—C23—H23B | 110.6 |
H11A—C11—H11B | 108.8 | H23A—C23—H23B | 108.7 |
O3—C12—N3 | 128.80 (13) | O6—C24—N6 | 128.58 (13) |
O3—C12—O2 | 120.95 (12) | O6—C24—O5 | 120.87 (13) |
N3—C12—O2 | 110.24 (11) | N6—C24—O5 | 110.52 (11) |
C7—N1—N2 | 117.21 (12) | C19—N4—N5 | 118.38 (11) |
C9—N2—N1 | 116.92 (11) | C21—N5—N4 | 115.79 (11) |
C9—N2—C8 | 120.65 (11) | C21—N5—C20 | 121.66 (11) |
N1—N2—C8 | 122.24 (11) | N4—N5—C20 | 122.40 (11) |
C12—N3—C10 | 113.24 (11) | C24—N6—C22 | 112.48 (11) |
C12—N3—H1N | 118.6 (11) | C24—N6—H2N | 118.2 (11) |
C10—N3—H1N | 125.5 (11) | C22—N6—H2N | 124.0 (11) |
C12—O2—C11 | 109.80 (10) | C24—O5—C23 | 109.37 (10) |
C6—C1—C2—C3 | −1.9 (2) | C18—C13—C14—C15 | −0.4 (2) |
Cl1—C1—C2—C3 | 177.13 (11) | Cl2—C13—C14—C15 | −179.40 (11) |
C1—C2—C3—C4 | −0.3 (2) | C13—C14—C15—C16 | 0.8 (2) |
C2—C3—C4—C5 | 1.7 (2) | C14—C15—C16—C17 | −0.1 (2) |
C3—C4—C5—C6 | −0.9 (2) | C15—C16—C17—C18 | −1.0 (2) |
C4—C5—C6—C1 | −1.2 (2) | C14—C13—C18—C17 | −0.6 (2) |
C4—C5—C6—C7 | 178.07 (14) | Cl2—C13—C18—C17 | 178.39 (11) |
C2—C1—C6—C5 | 2.6 (2) | C14—C13—C18—C19 | 178.80 (13) |
Cl1—C1—C6—C5 | −176.37 (11) | Cl2—C13—C18—C19 | −2.26 (19) |
C2—C1—C6—C7 | −176.66 (13) | C16—C17—C18—C13 | 1.2 (2) |
Cl1—C1—C6—C7 | 4.32 (18) | C16—C17—C18—C19 | −178.11 (14) |
C5—C6—C7—N1 | −9.9 (2) | C13—C18—C19—N4 | 167.13 (13) |
C1—C6—C7—N1 | 169.41 (13) | C17—C18—C19—N4 | −13.5 (2) |
O1—C9—C10—N3 | −1.63 (18) | O4—C21—C22—N6 | −4.35 (18) |
N2—C9—C10—N3 | 178.44 (11) | N5—C21—C22—N6 | 175.76 (11) |
O1—C9—C10—C11 | −114.20 (14) | O4—C21—C22—C23 | −117.57 (14) |
N2—C9—C10—C11 | 65.87 (15) | N5—C21—C22—C23 | 62.54 (15) |
N3—C10—C11—O2 | −4.05 (13) | N6—C22—C23—O5 | 3.89 (13) |
C9—C10—C11—O2 | 114.01 (12) | C21—C22—C23—O5 | 123.35 (12) |
C6—C7—N1—N2 | −178.98 (12) | C18—C19—N4—N5 | −178.97 (11) |
O1—C9—N2—N1 | 178.75 (13) | O4—C21—N5—N4 | −174.42 (12) |
C10—C9—N2—N1 | −1.31 (18) | C22—C21—N5—N4 | 5.47 (16) |
O1—C9—N2—C8 | 3.7 (2) | O4—C21—N5—C20 | 1.2 (2) |
C10—C9—N2—C8 | −176.39 (13) | C22—C21—N5—C20 | −178.87 (12) |
C7—N1—N2—C9 | −175.91 (12) | C19—N4—N5—C21 | 174.24 (12) |
C7—N1—N2—C8 | −0.91 (19) | C19—N4—N5—C20 | −1.39 (19) |
O3—C12—N3—C10 | 174.04 (14) | O6—C24—N6—C22 | −173.57 (14) |
O2—C12—N3—C10 | −7.14 (16) | O5—C24—N6—C22 | 8.49 (16) |
C9—C10—N3—C12 | −113.51 (13) | C21—C22—N6—C24 | −127.83 (12) |
C11—C10—N3—C12 | 6.81 (15) | C23—C22—N6—C24 | −7.45 (14) |
O3—C12—O2—C11 | −177.11 (12) | O6—C24—O5—C23 | 176.42 (13) |
N3—C12—O2—C11 | 3.97 (15) | N6—C24—O5—C23 | −5.45 (15) |
C10—C11—O2—C12 | 0.36 (14) | C22—C23—O5—C24 | 0.61 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N···O6i | 0.873 (18) | 1.990 (18) | 2.8410 (16) | 164.7 (16) |
N6—H2N···O3ii | 0.869 (18) | 2.152 (18) | 2.9868 (16) | 161.1 (15) |
C8—H8C···Cl2iii | 0.98 | 2.62 | 3.5168 (17) | 153 |
C11—H11B···O3iv | 0.99 | 2.43 | 3.4067 (17) | 170 |
C15—H15···O4i | 0.95 | 2.48 | 3.1405 (18) | 127 |
C16—H16···O1 | 0.95 | 2.35 | 3.214 (2) | 152 |
C20—H20B···Cg3v | 0.98 | 2.84 | 3.5467 (16) | 130 |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) −x+1, −y, −z+1; (iv) x, −y+1/2, z+1/2; (v) −x+1, −y, −z+2. |
C12H12ClN3O3 | F(000) = 292 |
Mr = 281.70 | Dx = 1.539 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54187 Å |
a = 9.274 (4) Å | Cell parameters from 900 reflections |
b = 4.1096 (18) Å | θ = 22.6–68.4° |
c = 16.104 (7) Å | µ = 2.88 mm−1 |
β = 97.813 (9)° | T = 100 K |
V = 608.1 (5) Å3 | Needle, colourless |
Z = 2 | 0.60 × 0.04 × 0.02 mm |
CCD diffractometer | 1934 independent reflections |
Radiation source: fine-focus sealed tube | 1776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω scans | θmax = 69.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.277, Tmax = 0.945 | k = −4→4 |
5567 measured reflections | l = −19→19 |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0378P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1934 reflections | Δρmax = 0.28 e Å−3 |
176 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 526 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.054 (17) |
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 | ||
C1 | 0.6652 (3) | 0.2819 (8) | 0.12635 (14) | 0.0157 (6) | |
H1 | 0.5858 | 0.3991 | 0.1432 | 0.019* | |
C2 | 0.6531 (3) | 0.1512 (8) | 0.04637 (15) | 0.0174 (6) | |
H2 | 0.5662 | 0.1787 | 0.0083 | 0.021* | |
C3 | 0.7699 (3) | −0.0206 (7) | 0.02274 (15) | 0.0156 (6) | |
C4 | 0.8974 (3) | −0.0623 (7) | 0.07731 (15) | 0.0177 (7) | |
H4 | 0.9764 | −0.1810 | 0.0604 | 0.021* | |
C5 | 0.9081 (3) | 0.0713 (8) | 0.15672 (15) | 0.0177 (6) | |
H5 | 0.9956 | 0.0452 | 0.1943 | 0.021* | |
C6 | 0.7925 (3) | 0.2437 (7) | 0.18239 (14) | 0.0147 (7) | |
C7 | 0.8117 (3) | 0.3926 (7) | 0.26580 (15) | 0.0161 (6) | |
H7 | 0.9054 | 0.3963 | 0.2981 | 0.019* | |
C8 | 0.8710 (3) | 0.6957 (8) | 0.42061 (16) | 0.0221 (7) | |
H8A | 0.9121 | 0.4766 | 0.4290 | 0.033* | |
H8B | 0.8629 | 0.7948 | 0.4751 | 0.033* | |
H8C | 0.9347 | 0.8291 | 0.3907 | 0.033* | |
C9 | 0.6101 (2) | 0.8259 (9) | 0.39733 (13) | 0.0153 (6) | |
C10 | 0.4620 (2) | 0.7264 (7) | 0.35087 (14) | 0.0168 (7) | |
H10 | 0.4539 | 0.4838 | 0.3490 | 0.020* | |
C11 | 0.4249 (2) | 0.8679 (9) | 0.26145 (14) | 0.0183 (7) | |
H11A | 0.5046 | 1.0099 | 0.2477 | 0.022* | |
H11B | 0.4097 | 0.6908 | 0.2195 | 0.022* | |
C12 | 0.2491 (3) | 1.0320 (8) | 0.34004 (14) | 0.0168 (6) | |
N1 | 0.7026 (2) | 0.5182 (6) | 0.29560 (12) | 0.0158 (5) | |
N2 | 0.7272 (2) | 0.6757 (6) | 0.37152 (11) | 0.0145 (5) | |
N3 | 0.3457 (2) | 0.8615 (7) | 0.39094 (13) | 0.0192 (6) | |
H1N | 0.335 (3) | 0.791 (9) | 0.4426 (17) | 0.023* | |
O1 | 0.62190 (19) | 1.0110 (5) | 0.45697 (11) | 0.0227 (5) | |
O2 | 0.29284 (18) | 1.0528 (6) | 0.26243 (10) | 0.0207 (5) | |
O3 | 0.13829 (18) | 1.1634 (6) | 0.35500 (11) | 0.0241 (5) | |
Cl1 | 0.75467 (6) | −0.17898 (18) | −0.07843 (3) | 0.02190 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0184 (12) | 0.0154 (18) | 0.0142 (10) | 0.0006 (13) | 0.0051 (9) | 0.0017 (13) |
C2 | 0.0183 (13) | 0.0187 (18) | 0.0146 (12) | 0.0006 (13) | −0.0001 (10) | 0.0024 (13) |
C3 | 0.0203 (13) | 0.0139 (17) | 0.0132 (12) | −0.0040 (12) | 0.0049 (10) | 0.0011 (12) |
C4 | 0.0202 (13) | 0.0177 (18) | 0.0160 (12) | 0.0035 (12) | 0.0052 (10) | 0.0012 (12) |
C5 | 0.0181 (13) | 0.0190 (18) | 0.0160 (12) | 0.0025 (12) | 0.0024 (10) | 0.0009 (13) |
C6 | 0.0177 (12) | 0.0121 (19) | 0.0149 (11) | −0.0024 (11) | 0.0043 (10) | 0.0031 (11) |
C7 | 0.0169 (12) | 0.0169 (19) | 0.0141 (11) | 0.0009 (12) | 0.0004 (9) | 0.0013 (12) |
C8 | 0.0187 (13) | 0.029 (2) | 0.0168 (12) | 0.0000 (13) | −0.0027 (10) | −0.0019 (13) |
C9 | 0.0219 (12) | 0.0132 (15) | 0.0108 (10) | 0.0008 (14) | 0.0020 (9) | 0.0044 (14) |
C10 | 0.0185 (13) | 0.0170 (19) | 0.0149 (11) | 0.0014 (11) | 0.0017 (10) | −0.0009 (11) |
C11 | 0.0167 (12) | 0.026 (2) | 0.0117 (10) | 0.0007 (13) | 0.0003 (9) | −0.0002 (14) |
C12 | 0.0150 (13) | 0.0210 (18) | 0.0137 (12) | −0.0024 (13) | −0.0007 (10) | 0.0012 (13) |
N1 | 0.0192 (11) | 0.0169 (15) | 0.0112 (9) | −0.0020 (10) | 0.0017 (8) | −0.0008 (10) |
N2 | 0.0167 (10) | 0.0159 (14) | 0.0103 (9) | 0.0004 (10) | −0.0007 (8) | −0.0023 (10) |
N3 | 0.0192 (10) | 0.0260 (17) | 0.0133 (9) | 0.0051 (12) | 0.0052 (8) | 0.0045 (12) |
O1 | 0.0277 (10) | 0.0233 (14) | 0.0167 (9) | −0.0015 (9) | 0.0018 (7) | −0.0069 (9) |
O2 | 0.0172 (9) | 0.0322 (14) | 0.0129 (8) | 0.0046 (9) | 0.0022 (7) | 0.0076 (9) |
O3 | 0.0161 (9) | 0.0322 (14) | 0.0243 (9) | 0.0049 (9) | 0.0038 (7) | 0.0026 (10) |
Cl1 | 0.0240 (3) | 0.0270 (4) | 0.0145 (3) | 0.0017 (3) | 0.0019 (2) | −0.0037 (4) |
C1—C2 | 1.386 (3) | C8—H8B | 0.9800 |
C1—C6 | 1.394 (3) | C8—H8C | 0.9800 |
C1—H1 | 0.9500 | C9—O1 | 1.219 (3) |
C2—C3 | 1.389 (4) | C9—N2 | 1.362 (3) |
C2—H2 | 0.9500 | C9—C10 | 1.528 (3) |
C3—C4 | 1.385 (3) | C10—N3 | 1.441 (3) |
C3—Cl1 | 1.742 (3) | C10—C11 | 1.548 (3) |
C4—C5 | 1.383 (4) | C10—H10 | 1.0000 |
C4—H4 | 0.9500 | C11—O2 | 1.444 (3) |
C5—C6 | 1.394 (4) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.465 (3) | C12—O3 | 1.213 (3) |
C7—N1 | 1.285 (3) | C12—N3 | 1.329 (4) |
C7—H7 | 0.9500 | C12—O2 | 1.368 (3) |
C8—N2 | 1.457 (3) | N1—N2 | 1.375 (3) |
C8—H8A | 0.9800 | N3—H1N | 0.90 (3) |
C2—C1—C6 | 120.8 (2) | O1—C9—N2 | 122.2 (2) |
C2—C1—H1 | 119.6 | O1—C9—C10 | 122.1 (2) |
C6—C1—H1 | 119.6 | N2—C9—C10 | 115.5 (2) |
C1—C2—C3 | 118.9 (2) | N3—C10—C9 | 110.8 (2) |
C1—C2—H2 | 120.5 | N3—C10—C11 | 100.77 (19) |
C3—C2—H2 | 120.5 | C9—C10—C11 | 115.2 (2) |
C4—C3—C2 | 121.3 (2) | N3—C10—H10 | 109.9 |
C4—C3—Cl1 | 120.0 (2) | C9—C10—H10 | 109.9 |
C2—C3—Cl1 | 118.63 (19) | C11—C10—H10 | 109.9 |
C5—C4—C3 | 119.0 (2) | O2—C11—C10 | 105.60 (18) |
C5—C4—H4 | 120.5 | O2—C11—H11A | 110.6 |
C3—C4—H4 | 120.5 | C10—C11—H11A | 110.6 |
C4—C5—C6 | 121.0 (2) | O2—C11—H11B | 110.6 |
C4—C5—H5 | 119.5 | C10—C11—H11B | 110.6 |
C6—C5—H5 | 119.5 | H11A—C11—H11B | 108.8 |
C1—C6—C5 | 118.9 (2) | O3—C12—N3 | 129.1 (2) |
C1—C6—C7 | 122.2 (2) | O3—C12—O2 | 121.2 (2) |
C5—C6—C7 | 118.8 (2) | N3—C12—O2 | 109.7 (2) |
N1—C7—C6 | 120.4 (2) | C7—N1—N2 | 118.53 (19) |
N1—C7—H7 | 119.8 | C9—N2—N1 | 116.24 (18) |
C6—C7—H7 | 119.8 | C9—N2—C8 | 121.2 (2) |
N2—C8—H8A | 109.5 | N1—N2—C8 | 122.5 (2) |
N2—C8—H8B | 109.5 | C12—N3—C10 | 114.2 (2) |
H8A—C8—H8B | 109.5 | C12—N3—H1N | 126.4 (19) |
N2—C8—H8C | 109.5 | C10—N3—H1N | 118 (2) |
H8A—C8—H8C | 109.5 | C12—O2—C11 | 109.56 (19) |
H8B—C8—H8C | 109.5 | ||
C6—C1—C2—C3 | 0.3 (4) | N3—C10—C11—O2 | −1.6 (3) |
C1—C2—C3—C4 | −0.2 (4) | C9—C10—C11—O2 | −120.9 (2) |
C1—C2—C3—Cl1 | −179.1 (2) | C6—C7—N1—N2 | −175.5 (2) |
C2—C3—C4—C5 | −0.2 (4) | O1—C9—N2—N1 | −169.3 (3) |
Cl1—C3—C4—C5 | 178.7 (2) | C10—C9—N2—N1 | 15.3 (4) |
C3—C4—C5—C6 | 0.5 (4) | O1—C9—N2—C8 | 8.1 (4) |
C2—C1—C6—C5 | 0.0 (4) | C10—C9—N2—C8 | −167.3 (3) |
C2—C1—C6—C7 | 176.8 (3) | C7—N1—N2—C9 | 175.2 (3) |
C4—C5—C6—C1 | −0.4 (4) | C7—N1—N2—C8 | −2.2 (4) |
C4—C5—C6—C7 | −177.3 (3) | O3—C12—N3—C10 | 177.2 (3) |
C1—C6—C7—N1 | 11.8 (4) | O2—C12—N3—C10 | −4.3 (4) |
C5—C6—C7—N1 | −171.4 (3) | C9—C10—N3—C12 | 126.0 (3) |
O1—C9—C10—N3 | −4.0 (4) | C11—C10—N3—C12 | 3.6 (3) |
N2—C9—C10—N3 | 171.4 (2) | O3—C12—O2—C11 | −178.4 (3) |
O1—C9—C10—C11 | 109.6 (3) | N3—C12—O2—C11 | 3.0 (3) |
N2—C9—C10—C11 | −75.0 (4) | C10—C11—O2—C12 | −0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N···O1i | 0.90 (3) | 1.98 (3) | 2.822 (3) | 155 (3) |
C7—H7···O3ii | 0.95 | 2.43 | 3.308 (3) | 154 |
C8—H8C···O3iii | 0.98 | 2.46 | 3.416 (4) | 164 |
C10—H10···O2iv | 1.00 | 2.60 | 3.398 (4) | 137 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x+1, y−1, z; (iii) x+1, y, z; (iv) x, y−1, z. |
C13H13Cl2N3O3 | Dx = 1.543 Mg m−3 |
Mr = 330.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P21212 | Cell parameters from 10413 reflections |
a = 19.7273 (13) Å | θ = 3.0–29.1° |
b = 7.6749 (3) Å | µ = 0.47 mm−1 |
c = 9.3882 (3) Å | T = 100 K |
V = 1421.42 (12) Å3 | Block, colourless |
Z = 4 | 0.11 × 0.10 × 0.08 mm |
F(000) = 680 |
Rigaku CCD diffractometer | 3655 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 29.1°, θmin = 3.0° |
ω scans | h = −26→22 |
10592 measured reflections | k = −8→10 |
3782 independent reflections | l = −8→12 |
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)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.058 | w = 1/[σ2(Fo2) + (0.0304P)2 + 0.292P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
3782 reflections | Δρmax = 0.29 e Å−3 |
192 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1508 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (4) |
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 | ||
C1 | 0.56269 (6) | 0.28819 (15) | 0.65767 (12) | 0.0142 (2) | |
C2 | 0.62682 (6) | 0.35432 (16) | 0.68474 (14) | 0.0179 (2) | |
H2 | 0.6581 | 0.3698 | 0.6088 | 0.021* | |
C3 | 0.64534 (6) | 0.39789 (17) | 0.82297 (15) | 0.0198 (3) | |
H3 | 0.6886 | 0.4479 | 0.8410 | 0.024* | |
C4 | 0.60086 (6) | 0.36852 (16) | 0.93442 (14) | 0.0181 (2) | |
H4 | 0.6134 | 0.3971 | 1.0293 | 0.022* | |
C5 | 0.53767 (6) | 0.29675 (15) | 0.90573 (12) | 0.0144 (2) | |
C6 | 0.51481 (5) | 0.25771 (17) | 0.76648 (11) | 0.01290 (19) | |
C7 | 0.44566 (6) | 0.19006 (16) | 0.74812 (12) | 0.0135 (2) | |
H7 | 0.4210 | 0.1544 | 0.8300 | 0.016* | |
C8 | 0.31324 (7) | 0.07201 (19) | 0.74848 (13) | 0.0190 (3) | |
H8A | 0.3106 | 0.1753 | 0.8096 | 0.029* | |
H8B | 0.3355 | −0.0229 | 0.8004 | 0.029* | |
H8C | 0.2674 | 0.0359 | 0.7210 | 0.029* | |
C9 | 0.32512 (6) | 0.09370 (16) | 0.48747 (13) | 0.0155 (2) | |
C10 | 0.36982 (7) | 0.15833 (17) | 0.36505 (13) | 0.0144 (2) | |
H10 | 0.4157 | 0.1032 | 0.3692 | 0.017* | |
C11 | 0.37560 (8) | 0.35994 (17) | 0.36365 (14) | 0.0202 (3) | |
H11A | 0.3526 | 0.4108 | 0.4476 | 0.024* | |
H11B | 0.4237 | 0.3965 | 0.3644 | 0.024* | |
C12 | 0.32291 (6) | 0.27228 (17) | 0.15739 (12) | 0.0155 (2) | |
C13 | 0.33253 (7) | −0.04779 (18) | 0.16878 (15) | 0.0225 (3) | |
H13A | 0.3092 | −0.1246 | 0.2363 | 0.034* | |
H13B | 0.3780 | −0.0935 | 0.1496 | 0.034* | |
H13C | 0.3068 | −0.0425 | 0.0796 | 0.034* | |
N1 | 0.41737 (5) | 0.17742 (14) | 0.62559 (11) | 0.01343 (19) | |
N2 | 0.35225 (5) | 0.11327 (14) | 0.62124 (11) | 0.0146 (2) | |
N3 | 0.33788 (6) | 0.12566 (15) | 0.22913 (11) | 0.0177 (2) | |
O1 | 0.26869 (5) | 0.03326 (14) | 0.46844 (10) | 0.0225 (2) | |
O2 | 0.34298 (5) | 0.41440 (12) | 0.23429 (10) | 0.01758 (19) | |
O3 | 0.29591 (5) | 0.28803 (14) | 0.04279 (9) | 0.0235 (2) | |
Cl1 | 0.545810 (13) | 0.23992 (4) | 0.47978 (3) | 0.01687 (6) | |
Cl2 | 0.485825 (14) | 0.25546 (5) | 1.05296 (3) | 0.01923 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0141 (5) | 0.0118 (5) | 0.0168 (5) | 0.0013 (4) | −0.0007 (4) | 0.0008 (4) |
C2 | 0.0133 (5) | 0.0157 (6) | 0.0246 (6) | 0.0003 (5) | 0.0012 (5) | 0.0045 (5) |
C3 | 0.0126 (5) | 0.0149 (6) | 0.0320 (7) | −0.0008 (5) | −0.0060 (5) | 0.0010 (5) |
C4 | 0.0176 (6) | 0.0155 (6) | 0.0212 (6) | 0.0019 (5) | −0.0067 (5) | −0.0014 (4) |
C5 | 0.0142 (5) | 0.0136 (5) | 0.0154 (5) | 0.0017 (4) | −0.0004 (4) | −0.0006 (4) |
C6 | 0.0121 (5) | 0.0115 (5) | 0.0151 (4) | 0.0012 (5) | −0.0014 (4) | 0.0000 (4) |
C7 | 0.0121 (5) | 0.0139 (5) | 0.0146 (5) | 0.0000 (4) | 0.0001 (4) | 0.0004 (4) |
C8 | 0.0154 (6) | 0.0259 (7) | 0.0158 (5) | −0.0056 (5) | 0.0027 (5) | −0.0017 (5) |
C9 | 0.0127 (5) | 0.0186 (6) | 0.0153 (5) | 0.0017 (4) | −0.0014 (4) | −0.0003 (4) |
C10 | 0.0146 (5) | 0.0158 (5) | 0.0127 (5) | 0.0012 (5) | −0.0023 (4) | −0.0004 (4) |
C11 | 0.0272 (7) | 0.0158 (6) | 0.0175 (6) | 0.0010 (5) | −0.0067 (5) | −0.0006 (5) |
C12 | 0.0107 (4) | 0.0212 (6) | 0.0144 (4) | 0.0024 (5) | 0.0022 (4) | 0.0011 (5) |
C13 | 0.0240 (6) | 0.0198 (6) | 0.0238 (6) | 0.0006 (6) | −0.0019 (5) | −0.0084 (5) |
N1 | 0.0104 (4) | 0.0142 (4) | 0.0157 (4) | −0.0009 (4) | −0.0008 (4) | 0.0008 (4) |
N2 | 0.0103 (4) | 0.0193 (5) | 0.0141 (4) | −0.0023 (4) | −0.0001 (4) | 0.0002 (4) |
N3 | 0.0233 (6) | 0.0164 (5) | 0.0133 (5) | 0.0004 (4) | −0.0046 (4) | −0.0025 (4) |
O1 | 0.0133 (4) | 0.0346 (6) | 0.0197 (4) | −0.0047 (4) | −0.0023 (3) | −0.0018 (4) |
O2 | 0.0206 (5) | 0.0167 (4) | 0.0154 (4) | 0.0027 (4) | −0.0011 (4) | 0.0013 (3) |
O3 | 0.0229 (4) | 0.0336 (6) | 0.0138 (4) | 0.0045 (4) | −0.0032 (3) | 0.0032 (4) |
Cl1 | 0.01605 (12) | 0.01956 (13) | 0.01500 (11) | −0.00092 (12) | 0.00214 (9) | 0.00018 (11) |
Cl2 | 0.01828 (12) | 0.02584 (15) | 0.01357 (11) | 0.00114 (14) | −0.00100 (9) | −0.00086 (12) |
C1—C2 | 1.3866 (17) | C9—O1 | 1.2192 (15) |
C1—C6 | 1.4109 (15) | C9—N2 | 1.3734 (15) |
C1—Cl1 | 1.7427 (12) | C9—C10 | 1.5312 (17) |
C2—C3 | 1.3890 (19) | C10—N3 | 1.4450 (16) |
C2—H2 | 0.9500 | C10—C11 | 1.5516 (17) |
C3—C4 | 1.3840 (19) | C10—H10 | 1.0000 |
C3—H3 | 0.9500 | C11—O2 | 1.4366 (15) |
C4—C5 | 1.3891 (17) | C11—H11A | 0.9900 |
C4—H4 | 0.9500 | C11—H11B | 0.9900 |
C5—C6 | 1.4150 (15) | C12—O3 | 1.2066 (14) |
C5—Cl2 | 1.7485 (12) | C12—N3 | 1.3444 (16) |
C6—C7 | 1.4696 (15) | C12—O2 | 1.3666 (15) |
C7—N1 | 1.2822 (15) | C13—N3 | 1.4506 (17) |
C7—H7 | 0.9500 | C13—H13A | 0.9800 |
C8—N2 | 1.4558 (15) | C13—H13B | 0.9800 |
C8—H8A | 0.9800 | C13—H13C | 0.9800 |
C8—H8B | 0.9800 | N1—N2 | 1.3763 (14) |
C8—H8C | 0.9800 | ||
C2—C1—C6 | 122.60 (11) | N3—C10—C9 | 110.82 (11) |
C2—C1—Cl1 | 115.33 (9) | N3—C10—C11 | 101.40 (11) |
C6—C1—Cl1 | 122.05 (9) | C9—C10—C11 | 111.82 (11) |
C1—C2—C3 | 119.96 (12) | N3—C10—H10 | 110.8 |
C1—C2—H2 | 120.0 | C9—C10—H10 | 110.8 |
C3—C2—H2 | 120.0 | C11—C10—H10 | 110.8 |
C4—C3—C2 | 120.02 (12) | O2—C11—C10 | 105.33 (11) |
C4—C3—H3 | 120.0 | O2—C11—H11A | 110.7 |
C2—C3—H3 | 120.0 | C10—C11—H11A | 110.7 |
C3—C4—C5 | 119.14 (12) | O2—C11—H11B | 110.7 |
C3—C4—H4 | 120.4 | C10—C11—H11B | 110.7 |
C5—C4—H4 | 120.4 | H11A—C11—H11B | 108.8 |
C4—C5—C6 | 123.31 (11) | O3—C12—N3 | 128.87 (13) |
C4—C5—Cl2 | 116.33 (9) | O3—C12—O2 | 121.27 (12) |
C6—C5—Cl2 | 120.36 (9) | N3—C12—O2 | 109.86 (9) |
C1—C6—C5 | 114.86 (10) | N3—C13—H13A | 109.5 |
C1—C6—C7 | 126.51 (10) | N3—C13—H13B | 109.5 |
C5—C6—C7 | 118.62 (10) | H13A—C13—H13B | 109.5 |
N1—C7—C6 | 122.41 (10) | N3—C13—H13C | 109.5 |
N1—C7—H7 | 118.8 | H13A—C13—H13C | 109.5 |
C6—C7—H7 | 118.8 | H13B—C13—H13C | 109.5 |
N2—C8—H8A | 109.5 | C7—N1—N2 | 117.38 (10) |
N2—C8—H8B | 109.5 | C9—N2—N1 | 115.47 (10) |
H8A—C8—H8B | 109.5 | C9—N2—C8 | 121.36 (10) |
N2—C8—H8C | 109.5 | N1—N2—C8 | 123.15 (10) |
H8A—C8—H8C | 109.5 | C12—N3—C10 | 113.14 (10) |
H8B—C8—H8C | 109.5 | C12—N3—C13 | 123.81 (11) |
O1—C9—N2 | 122.11 (11) | C10—N3—C13 | 122.41 (11) |
O1—C9—C10 | 122.62 (11) | C12—O2—C11 | 110.13 (9) |
N2—C9—C10 | 115.25 (10) | ||
C6—C1—C2—C3 | −1.83 (19) | N3—C10—C11—O2 | 3.53 (15) |
Cl1—C1—C2—C3 | 179.70 (10) | C9—C10—C11—O2 | −114.60 (11) |
C1—C2—C3—C4 | 2.70 (19) | C6—C7—N1—N2 | −179.59 (11) |
C2—C3—C4—C5 | −0.56 (19) | O1—C9—N2—N1 | 177.75 (12) |
C3—C4—C5—C6 | −2.61 (19) | C10—C9—N2—N1 | −4.09 (15) |
C3—C4—C5—Cl2 | 177.46 (10) | O1—C9—N2—C8 | −3.64 (19) |
C2—C1—C6—C5 | −1.12 (17) | C10—C9—N2—C8 | 174.52 (11) |
Cl1—C1—C6—C5 | 177.26 (9) | C7—N1—N2—C9 | −176.87 (11) |
C2—C1—C6—C7 | 179.28 (12) | C7—N1—N2—C8 | 4.55 (17) |
Cl1—C1—C6—C7 | −2.34 (18) | O3—C12—N3—C10 | −179.38 (12) |
C4—C5—C6—C1 | 3.36 (18) | O2—C12—N3—C10 | 0.46 (14) |
Cl2—C5—C6—C1 | −176.71 (9) | O3—C12—N3—C13 | 9.6 (2) |
C4—C5—C6—C7 | −177.00 (11) | O2—C12—N3—C13 | −170.52 (12) |
Cl2—C5—C6—C7 | 2.93 (16) | C9—C10—N3—C12 | 116.32 (12) |
C1—C6—C7—N1 | −11.65 (19) | C11—C10—N3—C12 | −2.53 (15) |
C5—C6—C7—N1 | 168.76 (12) | C9—C10—N3—C13 | −72.56 (15) |
O1—C9—C10—N3 | −4.09 (17) | C11—C10—N3—C13 | 168.60 (13) |
N2—C9—C10—N3 | 177.76 (11) | O3—C12—O2—C11 | −178.05 (11) |
O1—C9—C10—C11 | 108.25 (15) | N3—C12—O2—C11 | 2.10 (13) |
N2—C9—C10—C11 | −69.90 (15) | C10—C11—O2—C12 | −3.56 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.95 | 2.42 | 3.2627 (16) | 148 |
C4—H4···O2ii | 0.95 | 2.56 | 3.4538 (16) | 158 |
C8—H8A···O3iii | 0.98 | 2.37 | 3.2404 (16) | 147 |
C8—H8C···O2iv | 0.98 | 2.41 | 3.3147 (17) | 154 |
C8—H8B···Cg2v | 0.98 | 2.85 | 3.7289 (15) | 149 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, z+1; (iii) x, y, z+1; (iv) −x+1/2, y−1/2, −z+1; (v) −x+1, −y, z. |