Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111037311/bk5105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037311/bk5105ld425sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037311/bk5105ld489sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037311/bk5105ld473sup4.hkl |
CCDC references: 861008; 861009; 861010
Data collection: Rigaku CrystalClear-SM Expert 2.0 r4 for ld425; COLLECT (Nonius BV, 1998) for ld489, ld473. Cell refinement: Rigaku CrystalClear-SM Expert 2.0 r4 for ld425; ? for ld489. Data reduction: Rigaku CrystalClear-SM Expert 2.0 r4 for ld425; ? for ld489. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for ld489, ld473. Software used to prepare material for publication: publCIF (Westrip, 2010) for ld489, ld473.
C13H14N2O3 | F(000) = 1040 |
Mr = 246.26 | Dx = 1.397 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6908 reflections |
a = 7.061 (5) Å | θ = 1.7–33.1° |
b = 24.489 (15) Å | µ = 0.10 mm−1 |
c = 13.930 (9) Å | T = 180 K |
β = 103.481 (8)° | Platelet, colorless |
V = 2342 (3) Å3 | 0.56 × 0.28 × 0.11 mm |
Z = 8 |
Rigaku CrystalClear-SM Expert 2.0 r4 diffractometer | 5763 independent reflections |
Radiation source: fine-focus sealed tube | 4634 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 28.3°, θmin = 2.9° |
profile data from ω–scans | h = −9→9 |
Absorption correction: multi-scan Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 | k = −32→32 |
Tmin = 0.973, Tmax = 1.028 | l = −18→18 |
14043 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | All H-atom parameters refined |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.1911P] where P = (Fo2 + 2Fc2)/3 |
5763 reflections | (Δ/σ)max = 0.001 |
437 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
C13H14N2O3 | V = 2342 (3) Å3 |
Mr = 246.26 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.061 (5) Å | µ = 0.10 mm−1 |
b = 24.489 (15) Å | T = 180 K |
c = 13.930 (9) Å | 0.56 × 0.28 × 0.11 mm |
β = 103.481 (8)° |
Rigaku CrystalClear-SM Expert 2.0 r4 diffractometer | 5763 independent reflections |
Absorption correction: multi-scan Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 | 4634 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 1.028 | Rint = 0.077 |
14043 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.158 | All H-atom parameters refined |
S = 1.13 | Δρmax = 0.31 e Å−3 |
5763 reflections | Δρmin = −0.49 e Å−3 |
437 parameters |
Experimental. Rigaku CrystalClear-SM Expert 2.0 r4 |
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 | 0.9461 (3) | 0.32749 (8) | 0.51150 (14) | 0.0365 (4) | |
C2 | 1.0239 (3) | 0.31857 (6) | 0.79281 (13) | 0.0289 (4) | |
C3 | 0.9999 (3) | 0.33907 (6) | 0.69354 (13) | 0.0285 (3) | |
C4 | 0.9731 (3) | 0.30570 (6) | 0.61449 (12) | 0.0269 (3) | |
C5 | 0.9466 (3) | 0.20756 (7) | 0.55654 (13) | 0.0289 (3) | |
C6 | 0.9456 (3) | 0.15300 (7) | 0.58036 (13) | 0.0297 (4) | |
C7 | 0.9653 (3) | 0.13818 (6) | 0.68034 (13) | 0.0274 (3) | |
C8 | 0.9912 (2) | 0.22765 (6) | 0.72641 (12) | 0.0253 (3) | |
C9 | 0.9689 (3) | 0.24746 (6) | 0.63058 (12) | 0.0254 (3) | |
C10 | 0.8563 (3) | −0.00960 (7) | 0.67249 (16) | 0.0375 (4) | |
C11 | 0.9627 (3) | 0.03917 (7) | 0.64244 (15) | 0.0342 (4) | |
C12 | 1.0232 (3) | 0.07002 (7) | 0.81380 (14) | 0.0368 (4) | |
C13 | 0.9132 (4) | 0.02028 (7) | 0.83592 (16) | 0.0392 (4) | |
N1 | 0.9903 (2) | 0.17579 (5) | 0.75302 (10) | 0.0282 (3) | |
N2 | 0.9565 (2) | 0.08469 (5) | 0.70933 (11) | 0.0312 (3) | |
O1 | 1.0178 (2) | 0.26266 (4) | 0.80581 (9) | 0.0303 (3) | |
O2 | 1.0474 (2) | 0.34628 (5) | 0.86719 (9) | 0.0387 (3) | |
O3 | 0.9335 (2) | −0.02438 (5) | 0.77298 (11) | 0.0392 (3) | |
H3 | 1.007 (3) | 0.3794 (9) | 0.6895 (15) | 0.033 (5)* | |
H5 | 0.932 (3) | 0.2178 (9) | 0.4859 (16) | 0.040 (6)* | |
H6 | 0.933 (4) | 0.1269 (10) | 0.5321 (17) | 0.044 (6)* | |
H10A | 0.718 (4) | −0.0011 (9) | 0.6641 (16) | 0.040 (6)* | |
H11A | 0.894 (4) | 0.0492 (9) | 0.5699 (17) | 0.041 (6)* | |
H12A | 0.994 (4) | 0.1002 (10) | 0.8522 (18) | 0.049 (7)* | |
H13A | 0.767 (4) | 0.0294 (9) | 0.8267 (17) | 0.047 (7)* | |
H10B | 0.873 (3) | −0.0424 (8) | 0.6329 (15) | 0.032 (5)* | |
H11B | 1.096 (4) | 0.0303 (9) | 0.6439 (16) | 0.039 (6)* | |
H12B | 1.163 (3) | 0.0635 (9) | 0.8302 (16) | 0.034 (6)* | |
H13B | 0.975 (3) | 0.0070 (9) | 0.9046 (17) | 0.042 (6)* | |
H1A | 0.813 (4) | 0.3148 (10) | 0.4693 (17) | 0.052 (7)* | |
H1B | 0.952 (4) | 0.3694 (9) | 0.5139 (16) | 0.043 (6)* | |
H1C | 1.044 (4) | 0.3129 (10) | 0.4814 (17) | 0.050 (7)* | |
C1' | 0.5723 (3) | 0.60840 (7) | 0.95517 (14) | 0.0351 (4) | |
C2' | 0.5056 (3) | 0.63447 (7) | 0.67842 (13) | 0.0311 (4) | |
C3' | 0.5351 (3) | 0.60840 (6) | 0.77339 (13) | 0.0296 (4) | |
C4' | 0.5482 (3) | 0.63685 (6) | 0.85765 (13) | 0.0278 (3) | |
C5' | 0.5510 (3) | 0.73147 (7) | 0.93349 (13) | 0.0291 (4) | |
C6' | 0.5393 (3) | 0.78692 (7) | 0.91930 (13) | 0.0300 (4) | |
C7' | 0.5129 (3) | 0.80747 (6) | 0.82181 (13) | 0.0274 (3) | |
C8' | 0.5105 (3) | 0.72095 (6) | 0.76077 (12) | 0.0267 (3) | |
C9' | 0.5359 (2) | 0.69574 (6) | 0.85298 (12) | 0.0262 (3) | |
C10' | 0.4305 (3) | 0.95433 (7) | 0.84990 (16) | 0.0381 (4) | |
C11' | 0.5584 (3) | 0.90424 (7) | 0.87593 (15) | 0.0346 (4) | |
C12' | 0.4811 (3) | 0.88138 (7) | 0.70015 (14) | 0.0340 (4) | |
C13' | 0.3556 (3) | 0.93232 (7) | 0.68180 (16) | 0.0371 (4) | |
N1' | 0.4991 (2) | 0.77406 (6) | 0.74347 (10) | 0.0284 (3) | |
N2' | 0.4932 (3) | 0.86204 (5) | 0.80112 (11) | 0.0324 (3) | |
O1' | 0.4949 (2) | 0.69094 (5) | 0.67596 (9) | 0.0313 (3) | |
O2' | 0.4875 (2) | 0.61180 (5) | 0.59927 (10) | 0.0411 (3) | |
O3' | 0.4279 (2) | 0.97386 (5) | 0.75282 (11) | 0.0387 (3) | |
H3' | 0.538 (3) | 0.5695 (10) | 0.7721 (16) | 0.039 (6)* | |
H5' | 0.566 (3) | 0.7175 (9) | 1.0013 (15) | 0.036 (6)* | |
H6' | 0.547 (3) | 0.8105 (9) | 0.9725 (15) | 0.037 (6)* | |
H10C | 0.289 (4) | 0.9457 (9) | 0.8536 (17) | 0.044 (6)* | |
H11C | 0.554 (4) | 0.8922 (9) | 0.9401 (17) | 0.040 (6)* | |
H12C | 0.419 (4) | 0.8540 (9) | 0.6579 (16) | 0.043 (6)* | |
H13C | 0.215 (3) | 0.9233 (9) | 0.6834 (16) | 0.037 (6)* | |
H10D | 0.482 (3) | 0.9822 (9) | 0.8955 (16) | 0.039 (6)* | |
H11D | 0.696 (4) | 0.9148 (10) | 0.8762 (17) | 0.046 (6)* | |
H12D | 0.616 (3) | 0.8896 (9) | 0.6928 (15) | 0.032 (5)* | |
H13D | 0.366 (4) | 0.9486 (9) | 0.6128 (17) | 0.044 (6)* | |
H1D | 0.459 (4) | 0.6172 (9) | 0.9843 (17) | 0.043 (6)* | |
H1E | 0.588 (4) | 0.5682 (10) | 0.9486 (17) | 0.044 (6)* | |
H1F | 0.684 (4) | 0.6220 (9) | 1.0033 (17) | 0.041 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0478 (12) | 0.0315 (8) | 0.0297 (9) | 0.0035 (8) | 0.0077 (8) | 0.0065 (7) |
C2 | 0.0347 (9) | 0.0217 (7) | 0.0310 (8) | −0.0027 (6) | 0.0094 (7) | −0.0014 (6) |
C3 | 0.0322 (9) | 0.0226 (7) | 0.0319 (8) | 0.0007 (6) | 0.0098 (7) | 0.0016 (6) |
C4 | 0.0263 (8) | 0.0249 (7) | 0.0297 (8) | 0.0020 (6) | 0.0071 (7) | 0.0039 (6) |
C5 | 0.0319 (9) | 0.0269 (7) | 0.0289 (8) | −0.0004 (6) | 0.0087 (7) | −0.0021 (6) |
C6 | 0.0340 (9) | 0.0254 (7) | 0.0312 (8) | −0.0011 (7) | 0.0102 (7) | −0.0049 (6) |
C7 | 0.0285 (8) | 0.0221 (7) | 0.0331 (8) | 0.0003 (6) | 0.0104 (7) | −0.0011 (6) |
C8 | 0.0267 (8) | 0.0232 (7) | 0.0273 (8) | 0.0003 (6) | 0.0086 (6) | −0.0009 (6) |
C9 | 0.0264 (8) | 0.0232 (7) | 0.0266 (8) | 0.0009 (6) | 0.0060 (6) | 0.0000 (6) |
C10 | 0.0377 (10) | 0.0242 (7) | 0.0496 (11) | −0.0027 (7) | 0.0081 (9) | −0.0028 (7) |
C11 | 0.0408 (10) | 0.0227 (7) | 0.0417 (10) | −0.0007 (7) | 0.0146 (8) | −0.0053 (7) |
C12 | 0.0506 (12) | 0.0240 (7) | 0.0360 (9) | −0.0043 (8) | 0.0105 (9) | 0.0016 (7) |
C13 | 0.0494 (12) | 0.0257 (8) | 0.0457 (11) | −0.0010 (8) | 0.0175 (10) | 0.0033 (7) |
N1 | 0.0339 (8) | 0.0213 (6) | 0.0304 (7) | −0.0009 (5) | 0.0097 (6) | 0.0005 (5) |
N2 | 0.0403 (9) | 0.0204 (6) | 0.0341 (7) | −0.0012 (6) | 0.0110 (7) | −0.0011 (5) |
O1 | 0.0444 (8) | 0.0208 (5) | 0.0265 (6) | −0.0017 (5) | 0.0100 (5) | 0.0002 (4) |
O2 | 0.0597 (10) | 0.0257 (5) | 0.0324 (7) | −0.0051 (6) | 0.0142 (7) | −0.0041 (5) |
O3 | 0.0437 (8) | 0.0213 (5) | 0.0524 (8) | −0.0007 (5) | 0.0110 (7) | 0.0027 (5) |
C1' | 0.0441 (11) | 0.0280 (8) | 0.0324 (9) | −0.0003 (8) | 0.0072 (8) | 0.0054 (7) |
C2' | 0.0338 (9) | 0.0241 (7) | 0.0346 (9) | 0.0025 (6) | 0.0065 (7) | −0.0014 (6) |
C3' | 0.0329 (9) | 0.0200 (7) | 0.0347 (9) | −0.0001 (6) | 0.0056 (7) | 0.0011 (6) |
C4' | 0.0247 (8) | 0.0242 (7) | 0.0335 (8) | −0.0015 (6) | 0.0048 (7) | 0.0017 (6) |
C5' | 0.0317 (9) | 0.0262 (7) | 0.0300 (8) | −0.0018 (6) | 0.0084 (7) | 0.0016 (6) |
C6' | 0.0344 (9) | 0.0257 (7) | 0.0314 (8) | −0.0015 (7) | 0.0109 (7) | −0.0034 (6) |
C7' | 0.0267 (8) | 0.0228 (7) | 0.0337 (8) | 0.0001 (6) | 0.0093 (7) | 0.0005 (6) |
C8' | 0.0277 (8) | 0.0237 (7) | 0.0290 (8) | −0.0005 (6) | 0.0071 (7) | −0.0021 (6) |
C9' | 0.0251 (8) | 0.0232 (7) | 0.0298 (8) | −0.0013 (6) | 0.0059 (7) | 0.0018 (6) |
C10' | 0.0445 (11) | 0.0236 (7) | 0.0503 (11) | 0.0004 (8) | 0.0197 (9) | −0.0037 (7) |
C11' | 0.0441 (11) | 0.0235 (7) | 0.0385 (9) | −0.0015 (7) | 0.0139 (8) | −0.0023 (7) |
C12' | 0.0437 (11) | 0.0238 (7) | 0.0369 (9) | 0.0032 (7) | 0.0144 (8) | 0.0027 (7) |
C13' | 0.0399 (11) | 0.0246 (7) | 0.0466 (11) | 0.0022 (7) | 0.0099 (9) | 0.0022 (7) |
N1' | 0.0327 (8) | 0.0230 (6) | 0.0295 (7) | 0.0018 (5) | 0.0074 (6) | 0.0015 (5) |
N2' | 0.0452 (9) | 0.0204 (6) | 0.0336 (7) | 0.0009 (6) | 0.0132 (7) | 0.0005 (5) |
O1' | 0.0413 (7) | 0.0227 (5) | 0.0293 (6) | 0.0024 (5) | 0.0073 (5) | 0.0004 (4) |
O2' | 0.0603 (10) | 0.0289 (6) | 0.0327 (7) | 0.0056 (6) | 0.0079 (7) | −0.0038 (5) |
O3' | 0.0457 (8) | 0.0209 (5) | 0.0507 (8) | −0.0011 (5) | 0.0137 (7) | 0.0008 (5) |
C6—C7 | 1.414 (3) | C10—C11 | 1.521 (3) |
C7—N1 | 1.350 (2) | C10—H10A | 0.98 (2) |
C8—N1 | 1.324 (2) | C10—H10B | 1.00 (2) |
C8—C9 | 1.394 (2) | C11—N2 | 1.460 (2) |
C5—C9 | 1.403 (2) | C11—H11A | 1.04 (2) |
C5—C6 | 1.377 (2) | C11—H11B | 0.96 (2) |
C8—O1 | 1.377 (2) | C12—N2 | 1.466 (2) |
C2—O1 | 1.383 (2) | C12—C13 | 1.514 (3) |
C2—C3 | 1.444 (2) | C12—H12A | 0.96 (3) |
C3—C4 | 1.349 (2) | C12—H12B | 0.98 (2) |
C4—C9 | 1.445 (2) | C13—O3 | 1.430 (2) |
C2—O2 | 1.217 (2) | C13—H13A | 1.03 (3) |
C6'—C7' | 1.419 (2) | C13—H13B | 1.01 (2) |
C7'—N1' | 1.349 (2) | C1'—C4' | 1.501 (2) |
C8'—N1' | 1.322 (2) | C1'—H1D | 1.00 (3) |
C8'—C9' | 1.398 (2) | C1'—H1E | 1.00 (2) |
C5'—C9' | 1.407 (2) | C1'—H1F | 0.97 (2) |
C5'—C6' | 1.372 (2) | C3'—H3' | 0.95 (2) |
C8'—O1' | 1.374 (2) | C5'—H5' | 0.99 (2) |
C2'—O1' | 1.385 (2) | C6'—H6' | 0.93 (2) |
C2'—C3' | 1.440 (2) | C10'—O3' | 1.431 (3) |
C3'—C4' | 1.349 (2) | C10'—C11' | 1.516 (3) |
C4'—C9' | 1.445 (2) | C10'—H10C | 1.04 (3) |
C2'—O2' | 1.214 (2) | C10'—H10D | 0.95 (2) |
C7—N2 | 1.376 (2) | C11'—N2' | 1.464 (2) |
C7'—N2' | 1.367 (2) | C11'—H11C | 0.95 (2) |
C1—C4 | 1.501 (2) | C11'—H11D | 1.00 (3) |
C1—H1A | 1.03 (3) | C12'—N2' | 1.468 (2) |
C1—H1B | 1.03 (2) | C12'—C13' | 1.517 (3) |
C1—H1C | 0.96 (3) | C12'—H12C | 0.93 (2) |
C3—H3 | 0.99 (2) | C12'—H12D | 1.00 (2) |
C5—H5 | 1.00 (2) | C13'—O3' | 1.428 (2) |
C6—H6 | 0.92 (2) | C13'—H13C | 1.02 (2) |
C10—O3 | 1.426 (3) | C13'—H13D | 1.06 (2) |
C4—C1—H1A | 109.4 (13) | C4'—C1'—H1D | 109.5 (13) |
C4—C1—H1B | 109.2 (12) | C4'—C1'—H1E | 111.5 (13) |
H1A—C1—H1B | 109.9 (19) | H1D—C1'—H1E | 111.6 (19) |
C4—C1—H1C | 110.0 (15) | C4'—C1'—H1F | 111.8 (14) |
H1A—C1—H1C | 107.0 (19) | H1D—C1'—H1F | 104.0 (19) |
H1B—C1—H1C | 111 (2) | H1E—C1'—H1F | 108.2 (19) |
O2—C2—O1 | 116.28 (15) | O2'—C2'—O1' | 116.13 (16) |
O2—C2—C3 | 125.72 (16) | O2'—C2'—C3' | 126.42 (16) |
O1—C2—C3 | 118.00 (14) | O1'—C2'—C3' | 117.45 (15) |
C4—C3—C2 | 122.28 (15) | C4'—C3'—C2' | 122.42 (15) |
C4—C3—H3 | 123.8 (12) | C4'—C3'—H3' | 122.4 (13) |
C2—C3—H3 | 113.9 (12) | C2'—C3'—H3' | 115.1 (13) |
C3—C4—C9 | 118.40 (15) | C3'—C4'—C9' | 119.01 (15) |
C3—C4—C1 | 121.83 (16) | C3'—C4'—C1' | 121.19 (15) |
C9—C4—C1 | 119.77 (15) | C9'—C4'—C1' | 119.80 (15) |
C6—C5—C9 | 120.31 (16) | C6'—C5'—C9' | 120.66 (16) |
C6—C5—H5 | 118.5 (13) | C6'—C5'—H5' | 118.0 (12) |
C9—C5—H5 | 121.2 (13) | C9'—C5'—H5' | 121.3 (12) |
C5—C6—C7 | 118.78 (15) | C5'—C6'—C7' | 118.61 (16) |
C5—C6—H6 | 120.3 (15) | C5'—C6'—H6' | 120.6 (13) |
C7—C6—H6 | 120.9 (15) | C7'—C6'—H6' | 120.7 (13) |
N1—C7—N2 | 115.86 (15) | N1'—C7'—N2' | 115.96 (15) |
N1—C7—C6 | 121.96 (15) | N1'—C7'—C6' | 121.83 (15) |
N2—C7—C6 | 122.17 (15) | N2'—C7'—C6' | 122.17 (15) |
N1—C8—O1 | 112.40 (14) | N1'—C8'—O1' | 112.35 (15) |
N1—C8—C9 | 126.53 (15) | N1'—C8'—C9' | 126.23 (15) |
O1—C8—C9 | 121.07 (14) | O1'—C8'—C9' | 121.42 (15) |
C8—C9—C5 | 115.46 (15) | C8'—C9'—C5' | 115.30 (15) |
C8—C9—C4 | 119.34 (15) | C8'—C9'—C4' | 118.37 (15) |
C5—C9—C4 | 125.20 (15) | C5'—C9'—C4' | 126.31 (15) |
O3—C10—C11 | 111.69 (16) | O3'—C10'—C11' | 111.85 (16) |
O3—C10—H10A | 108.2 (13) | O3'—C10'—H10C | 108.4 (13) |
C11—C10—H10A | 110.2 (13) | C11'—C10'—H10C | 110.6 (13) |
O3—C10—H10B | 105.7 (12) | O3'—C10'—H10D | 108.2 (14) |
C11—C10—H10B | 110.4 (12) | C11'—C10'—H10D | 108.1 (14) |
H10A—C10—H10B | 110.5 (18) | H10C—C10'—H10D | 109.7 (19) |
N2—C11—C10 | 109.48 (16) | N2'—C11'—C10' | 109.27 (17) |
N2—C11—H11A | 111.1 (13) | N2'—C11'—H11C | 112.2 (14) |
C10—C11—H11A | 107.6 (13) | C10'—C11'—H11C | 109.1 (14) |
N2—C11—H11B | 109.5 (13) | N2'—C11'—H11D | 109.1 (14) |
C10—C11—H11B | 111.1 (14) | C10'—C11'—H11D | 108.4 (14) |
H11A—C11—H11B | 107.9 (18) | H11C—C11'—H11D | 108.7 (19) |
N2—C12—C13 | 109.75 (17) | N2'—C12'—C13' | 109.14 (16) |
N2—C12—H12A | 107.7 (15) | N2'—C12'—H12C | 106.7 (14) |
C13—C12—H12A | 108.6 (15) | C13'—C12'—H12C | 108.5 (15) |
N2—C12—H12B | 110.3 (13) | N2'—C12'—H12D | 108.6 (12) |
C13—C12—H12B | 111.1 (13) | C13'—C12'—H12D | 110.5 (12) |
H12A—C12—H12B | 109 (2) | H12C—C12'—H12D | 113.3 (19) |
O3—C13—C12 | 111.18 (17) | O3'—C13'—C12' | 111.63 (17) |
O3—C13—H13A | 109.1 (13) | O3'—C13'—H13C | 109.3 (12) |
C12—C13—H13A | 110.2 (13) | C12'—C13'—H13C | 110.6 (12) |
O3—C13—H13B | 104.6 (13) | O3'—C13'—H13D | 105.7 (12) |
C12—C13—H13B | 108.8 (13) | C12'—C13'—H13D | 107.5 (13) |
H13A—C13—H13B | 112.8 (19) | H13C—C13'—H13D | 112.1 (18) |
C8—N1—C7 | 116.94 (15) | C8'—N1'—C7' | 117.35 (15) |
C7—N2—C11 | 121.95 (16) | C7'—N2'—C11' | 122.71 (16) |
C7—N2—C12 | 119.91 (14) | C7'—N2'—C12' | 119.85 (15) |
C11—N2—C12 | 113.31 (15) | C11'—N2'—C12' | 113.14 (14) |
C8—O1—C2 | 120.91 (13) | C8'—O1'—C2' | 121.32 (14) |
C10—O3—C13 | 109.75 (15) | C13'—O3'—C10' | 109.91 (14) |
C6—C7—N2—C11 | 11.6 (3) | C11—C10—O3—C13 | 60.5 (2) |
N1—C7—N2—C12 | −15.8 (3) | C12—C13—O3—C10 | −60.7 (2) |
C6'—C7'—N2'—C11' | 20.3 (3) | O2'—C2'—C3'—C4' | −178.1 (2) |
N1'—C7'—N2'—C12' | −6.8 (3) | O1'—C2'—C3'—C4' | 1.4 (3) |
O2—C2—C3—C4 | −179.52 (19) | C2'—C3'—C4'—C9' | −1.2 (3) |
O1—C2—C3—C4 | −0.3 (3) | C2'—C3'—C4'—C1' | 177.93 (18) |
C2—C3—C4—C9 | −0.1 (3) | C9'—C5'—C6'—C7' | −0.4 (3) |
C2—C3—C4—C1 | 179.33 (18) | C5'—C6'—C7'—N1' | 0.0 (3) |
C9—C5—C6—C7 | 0.7 (3) | C5'—C6'—C7'—N2' | 177.74 (18) |
C5—C6—C7—N1 | −1.8 (3) | N1'—C8'—C9'—C5' | −0.3 (3) |
C5—C6—C7—N2 | 176.89 (18) | O1'—C8'—C9'—C5' | 179.55 (16) |
N1—C8—C9—C5 | −1.1 (3) | N1'—C8'—C9'—C4' | −179.00 (17) |
O1—C8—C9—C5 | 178.85 (15) | O1'—C8'—C9'—C4' | 0.9 (3) |
N1—C8—C9—C4 | 179.81 (18) | C6'—C5'—C9'—C8' | 0.5 (3) |
O1—C8—C9—C4 | −0.2 (3) | C6'—C5'—C9'—C4' | 179.12 (18) |
C6—C5—C9—C8 | 0.7 (3) | C3'—C4'—C9'—C8' | 0.0 (3) |
C6—C5—C9—C4 | 179.70 (18) | C1'—C4'—C9'—C8' | −179.06 (16) |
C3—C4—C9—C8 | 0.4 (3) | C3'—C4'—C9'—C5' | −178.50 (17) |
C1—C4—C9—C8 | −179.06 (17) | C1'—C4'—C9'—C5' | 2.4 (3) |
C3—C4—C9—C5 | −178.56 (17) | O3'—C10'—C11'—N2' | −55.8 (2) |
C1—C4—C9—C5 | 1.9 (3) | N2'—C12'—C13'—O3' | 56.4 (2) |
O3—C10—C11—N2 | −55.6 (2) | O1'—C8'—N1'—C7' | −179.94 (15) |
N2—C12—C13—O3 | 56.2 (2) | C9'—C8'—N1'—C7' | −0.1 (3) |
O1—C8—N1—C7 | −179.92 (15) | N2'—C7'—N1'—C8' | −177.62 (17) |
C9—C8—N1—C7 | 0.0 (3) | C6'—C7'—N1'—C8' | 0.2 (3) |
N2—C7—N1—C8 | −177.33 (17) | N1'—C7'—N2'—C11' | −161.88 (18) |
C6—C7—N1—C8 | 1.5 (3) | C6'—C7'—N2'—C12' | 175.38 (17) |
N1—C7—N2—C11 | −169.55 (17) | C10'—C11'—N2'—C7' | −150.07 (18) |
C6—C7—N2—C12 | 165.38 (18) | C10'—C11'—N2'—C12' | 53.3 (2) |
C10—C11—N2—C7 | −152.67 (18) | C13'—C12'—N2'—C7' | 149.04 (18) |
C10—C11—N2—C12 | 52.0 (2) | C13'—C12'—N2'—C11' | −53.6 (2) |
C13—C12—N2—C7 | 151.52 (18) | N1'—C8'—O1'—C2' | 179.24 (16) |
C13—C12—N2—C11 | −52.6 (2) | C9'—C8'—O1'—C2' | −0.6 (3) |
N1—C8—O1—C2 | 179.71 (16) | O2'—C2'—O1'—C8' | 179.05 (17) |
C9—C8—O1—C2 | −0.2 (3) | C3'—C2'—O1'—C8' | −0.4 (3) |
O2—C2—O1—C8 | 179.79 (16) | C12'—C13'—O3'—C10' | −59.9 (2) |
C3—C2—O1—C8 | 0.5 (3) | C11'—C10'—O3'—C13' | 59.7 (2) |
C15H15F3N2O2 | F(000) = 648 |
Mr = 312.29 | Dx = 1.457 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11391 reflections |
a = 8.9941 (5) Å | θ = 1.0–27.5° |
b = 11.2954 (6) Å | µ = 0.12 mm−1 |
c = 14.3536 (9) Å | T = 180 K |
β = 102.537 (3)° | Unknown, orange |
V = 1423.44 (14) Å3 | 0.42 × 0.22 × 0.14 mm |
Z = 4 |
KappaCCD diffractometer | 3199 independent reflections |
Radiation source: fine-focus sealed tube | 2235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 9 pixels mm-1 | θmax = 27.4°, θmin = 3.8° |
CCD scans | h = −11→11 |
Absorption correction: multi-scan (Blessing, 1997) | k = −12→14 |
Tmin = 0.958, Tmax = 0.998 | l = −18→18 |
7357 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.3202P] where P = (Fo2 + 2Fc2)/3 |
3199 reflections | (Δ/σ)max = 0.002 |
259 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C15H15F3N2O2 | V = 1423.44 (14) Å3 |
Mr = 312.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.9941 (5) Å | µ = 0.12 mm−1 |
b = 11.2954 (6) Å | T = 180 K |
c = 14.3536 (9) Å | 0.42 × 0.22 × 0.14 mm |
β = 102.537 (3)° |
KappaCCD diffractometer | 3199 independent reflections |
Absorption correction: multi-scan (Blessing, 1997) | 2235 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.998 | Rint = 0.032 |
7357 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.127 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.31 e Å−3 |
3199 reflections | Δρmin = −0.25 e Å−3 |
259 parameters |
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 | 0.2477 (2) | 0.78948 (17) | 0.14985 (14) | 0.0391 (4) | |
C2 | 0.80818 (19) | 0.46523 (15) | 0.07362 (12) | 0.0325 (4) | |
C3 | 0.7898 (2) | 0.55964 (16) | 0.00517 (13) | 0.0330 (4) | |
C4 | 0.67916 (19) | 0.64196 (14) | 0.00119 (12) | 0.0290 (4) | |
C5 | 0.45757 (19) | 0.71682 (15) | 0.07080 (12) | 0.0300 (4) | |
C6 | 0.36822 (19) | 0.70197 (14) | 0.13569 (12) | 0.0305 (4) | |
C7 | 0.39573 (19) | 0.59913 (14) | 0.19546 (12) | 0.0294 (4) | |
C8 | 0.59412 (18) | 0.54420 (14) | 0.13010 (11) | 0.0277 (4) | |
C9 | 0.57626 (18) | 0.63679 (14) | 0.06469 (11) | 0.0269 (4) | |
C10 | 0.1224 (2) | 0.72198 (18) | 0.18203 (15) | 0.0398 (5) | |
C11 | 0.1795 (2) | 0.64828 (17) | 0.27112 (14) | 0.0390 (4) | |
C12 | 0.3571 (3) | 0.4805 (2) | 0.32947 (19) | 0.0539 (6) | |
C13 | 0.6682 (2) | 0.74157 (16) | −0.06926 (13) | 0.0378 (4) | |
C14 | 0.1864 (3) | 0.8655 (2) | 0.06277 (17) | 0.0493 (6) | |
C15 | 0.0514 (3) | 0.5755 (2) | 0.29548 (18) | 0.0517 (6) | |
F1 | 0.76268 (15) | 0.72983 (11) | −0.12794 (9) | 0.0596 (4) | |
F2 | 0.70122 (17) | 0.84548 (10) | −0.02397 (10) | 0.0636 (4) | |
F3 | 0.52873 (13) | 0.75268 (10) | −0.12364 (8) | 0.0505 (3) | |
H1 | 0.298 (3) | 0.844 (2) | 0.2072 (17) | 0.057 (6)* | |
H3 | 0.863 (2) | 0.5633 (16) | −0.0342 (13) | 0.035 (5)* | |
H5 | 0.440 (2) | 0.7812 (17) | 0.0288 (14) | 0.034 (5)* | |
H11 | 0.219 (2) | 0.705 (2) | 0.3271 (16) | 0.053 (6)* | |
H10A | 0.043 (2) | 0.7740 (18) | 0.1927 (14) | 0.045 (5)* | |
H12A | 0.346 (3) | 0.509 (3) | 0.395 (2) | 0.088 (9)* | |
H14A | 0.102 (3) | 0.917 (2) | 0.0727 (18) | 0.067 (7)* | |
H15A | −0.036 (3) | 0.628 (2) | 0.2940 (18) | 0.070 (8)* | |
H10B | 0.071 (2) | 0.6632 (19) | 0.1288 (16) | 0.051 (6)* | |
H12B | 0.459 (4) | 0.456 (3) | 0.328 (3) | 0.117 (12)* | |
H14B | 0.264 (3) | 0.918 (2) | 0.0478 (16) | 0.060 (7)* | |
H15B | 0.080 (3) | 0.537 (2) | 0.3598 (19) | 0.066 (7)* | |
H12C | 0.292 (4) | 0.419 (3) | 0.315 (2) | 0.092 (10)* | |
H14C | 0.139 (3) | 0.808 (3) | 0.009 (2) | 0.090 (9)* | |
H15C | 0.021 (3) | 0.507 (2) | 0.2430 (18) | 0.072 (7)* | |
N1 | 0.50978 (16) | 0.52345 (12) | 0.19248 (10) | 0.0304 (3) | |
N2 | 0.30719 (17) | 0.57286 (13) | 0.25804 (11) | 0.0357 (4) | |
O1 | 0.70763 (13) | 0.46132 (10) | 0.13396 (8) | 0.0330 (3) | |
O2 | 0.90560 (14) | 0.38881 (12) | 0.08503 (10) | 0.0439 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0448 (11) | 0.0323 (9) | 0.0432 (11) | 0.0059 (8) | 0.0163 (9) | −0.0015 (9) |
C2 | 0.0264 (8) | 0.0352 (9) | 0.0364 (9) | 0.0007 (7) | 0.0077 (7) | −0.0013 (8) |
C3 | 0.0280 (9) | 0.0392 (10) | 0.0339 (9) | −0.0017 (7) | 0.0112 (7) | −0.0001 (8) |
C4 | 0.0292 (8) | 0.0298 (9) | 0.0283 (8) | −0.0046 (7) | 0.0067 (7) | −0.0016 (7) |
C5 | 0.0346 (9) | 0.0242 (8) | 0.0320 (9) | −0.0011 (7) | 0.0088 (7) | 0.0018 (7) |
C6 | 0.0327 (9) | 0.0260 (8) | 0.0345 (9) | −0.0007 (7) | 0.0108 (7) | −0.0031 (7) |
C7 | 0.0320 (9) | 0.0299 (9) | 0.0273 (8) | −0.0041 (7) | 0.0091 (7) | −0.0036 (7) |
C8 | 0.0261 (8) | 0.0283 (8) | 0.0281 (8) | −0.0017 (7) | 0.0048 (7) | −0.0032 (7) |
C9 | 0.0284 (8) | 0.0261 (8) | 0.0262 (8) | −0.0018 (7) | 0.0056 (7) | −0.0004 (7) |
C10 | 0.0333 (10) | 0.0441 (11) | 0.0449 (11) | 0.0057 (9) | 0.0148 (8) | −0.0020 (10) |
C11 | 0.0384 (10) | 0.0423 (11) | 0.0401 (10) | −0.0010 (8) | 0.0167 (8) | −0.0058 (9) |
C12 | 0.0648 (16) | 0.0514 (14) | 0.0539 (14) | 0.0100 (12) | 0.0314 (12) | 0.0199 (12) |
C13 | 0.0406 (10) | 0.0370 (10) | 0.0400 (10) | 0.0007 (8) | 0.0177 (8) | 0.0036 (8) |
C14 | 0.0549 (14) | 0.0436 (12) | 0.0551 (13) | 0.0190 (11) | 0.0245 (11) | 0.0107 (11) |
C15 | 0.0439 (12) | 0.0638 (14) | 0.0524 (13) | −0.0065 (11) | 0.0215 (10) | 0.0027 (12) |
F1 | 0.0637 (8) | 0.0658 (8) | 0.0623 (8) | 0.0152 (6) | 0.0419 (7) | 0.0257 (7) |
F2 | 0.0959 (11) | 0.0341 (6) | 0.0653 (8) | −0.0164 (6) | 0.0275 (8) | 0.0021 (6) |
F3 | 0.0508 (7) | 0.0548 (7) | 0.0463 (6) | 0.0126 (5) | 0.0112 (5) | 0.0194 (6) |
N1 | 0.0319 (8) | 0.0296 (7) | 0.0313 (7) | 0.0006 (6) | 0.0100 (6) | 0.0020 (6) |
N2 | 0.0395 (8) | 0.0346 (8) | 0.0375 (8) | 0.0019 (6) | 0.0180 (7) | 0.0031 (7) |
O1 | 0.0302 (6) | 0.0335 (7) | 0.0369 (6) | 0.0061 (5) | 0.0110 (5) | 0.0066 (5) |
O2 | 0.0361 (7) | 0.0437 (8) | 0.0543 (8) | 0.0103 (6) | 0.0149 (6) | 0.0066 (7) |
C6—C7 | 1.433 (2) | C10—C11 | 1.519 (3) |
C7—N1 | 1.343 (2) | C10—H10A | 0.96 (2) |
C8—N1 | 1.314 (2) | C10—H10B | 1.04 (2) |
C8—C9 | 1.391 (2) | C11—N2 | 1.475 (2) |
C5—C9 | 1.416 (2) | C11—C15 | 1.517 (3) |
C5—C6 | 1.366 (2) | C11—H11 | 1.03 (2) |
C8—O1 | 1.377 (2) | C12—N2 | 1.464 (3) |
C2—O1 | 1.3820 (19) | C12—H12A | 1.01 (3) |
C2—C3 | 1.435 (2) | C12—H12B | 0.96 (4) |
C3—C4 | 1.354 (2) | C12—H12C | 0.91 (3) |
C4—C9 | 1.434 (2) | C13—F1 | 1.326 (2) |
C2—O2 | 1.215 (2) | C13—F3 | 1.332 (2) |
C7—N2 | 1.356 (2) | C13—F2 | 1.343 (2) |
C1—C6 | 1.513 (2) | C14—H14A | 0.99 (3) |
C1—C10 | 1.514 (3) | C14—H14B | 0.97 (2) |
C1—C14 | 1.518 (3) | C14—H14C | 1.03 (3) |
C1—H1 | 1.05 (2) | C15—H15A | 0.98 (3) |
C3—H3 | 0.954 (19) | C15—H15B | 1.00 (3) |
C4—C13 | 1.502 (2) | C15—H15C | 1.07 (3) |
C5—H5 | 0.936 (19) | ||
C6—C1—C10 | 108.34 (15) | N2—C11—C15 | 111.58 (17) |
C6—C1—C14 | 113.68 (16) | N2—C11—C10 | 109.87 (15) |
C10—C1—C14 | 112.00 (18) | C15—C11—C10 | 110.87 (18) |
C6—C1—H1 | 107.0 (12) | N2—C11—H11 | 108.0 (12) |
C10—C1—H1 | 106.2 (12) | C15—C11—H11 | 108.1 (12) |
C14—C1—H1 | 109.2 (12) | C10—C11—H11 | 108.3 (12) |
O2—C2—O1 | 116.33 (15) | N2—C12—H12A | 110.1 (16) |
O2—C2—C3 | 126.35 (16) | N2—C12—H12B | 110 (2) |
O1—C2—C3 | 117.31 (14) | H12A—C12—H12B | 113 (3) |
C4—C3—C2 | 120.92 (16) | N2—C12—H12C | 108 (2) |
C4—C3—H3 | 122.5 (11) | H12A—C12—H12C | 105 (2) |
C2—C3—H3 | 116.4 (11) | H12B—C12—H12C | 110 (3) |
C3—C4—C9 | 120.98 (15) | F1—C13—F3 | 106.80 (15) |
C3—C4—C13 | 118.88 (15) | F1—C13—F2 | 106.87 (15) |
C9—C4—C13 | 120.11 (15) | F3—C13—F2 | 106.39 (15) |
C6—C5—C9 | 121.79 (16) | F1—C13—C4 | 113.30 (15) |
C6—C5—H5 | 119.6 (11) | F3—C13—C4 | 112.38 (15) |
C9—C5—H5 | 118.6 (11) | F2—C13—C4 | 110.70 (15) |
C5—C6—C7 | 117.18 (15) | C1—C14—H14A | 111.6 (14) |
C5—C6—C1 | 123.78 (16) | C1—C14—H14B | 112.3 (14) |
C7—C6—C1 | 118.99 (15) | H14A—C14—H14B | 105.8 (19) |
N1—C7—N2 | 116.36 (15) | C1—C14—H14C | 106.5 (17) |
N1—C7—C6 | 122.05 (15) | H14A—C14—H14C | 106 (2) |
N2—C7—C6 | 121.59 (15) | H14B—C14—H14C | 114 (2) |
N1—C8—O1 | 112.57 (14) | C11—C15—H15A | 108.2 (15) |
N1—C8—C9 | 126.49 (15) | C11—C15—H15B | 112.9 (14) |
O1—C8—C9 | 120.94 (14) | H15A—C15—H15B | 109 (2) |
C8—C9—C5 | 114.60 (15) | C11—C15—H15C | 108.6 (13) |
C8—C9—C4 | 117.62 (15) | H15A—C15—H15C | 110 (2) |
C5—C9—C4 | 127.77 (15) | H15B—C15—H15C | 108.1 (19) |
C1—C10—C11 | 113.25 (17) | C8—N1—C7 | 117.77 (14) |
C1—C10—H10A | 111.8 (12) | C7—N2—C12 | 119.01 (16) |
C11—C10—H10A | 109.1 (12) | C7—N2—C11 | 122.92 (15) |
C1—C10—H10B | 109.7 (11) | C12—N2—C11 | 116.87 (16) |
C11—C10—H10B | 106.4 (11) | C8—O1—C2 | 122.22 (13) |
H10A—C10—H10B | 106.3 (17) | ||
C6—C7—N2—C11 | −1.4 (3) | C13—C4—C9—C5 | 0.3 (3) |
N1—C7—N2—C12 | 11.7 (3) | C6—C1—C10—C11 | 55.8 (2) |
O2—C2—C3—C4 | −177.94 (17) | C14—C1—C10—C11 | −178.04 (17) |
O1—C2—C3—C4 | 0.8 (2) | C1—C10—C11—N2 | −51.8 (2) |
C2—C3—C4—C9 | −0.5 (3) | C1—C10—C11—C15 | −175.60 (18) |
C2—C3—C4—C13 | 177.75 (16) | C3—C4—C13—F1 | 6.6 (2) |
C9—C5—C6—C7 | −2.2 (2) | C9—C4—C13—F1 | −175.14 (15) |
C9—C5—C6—C1 | 175.43 (17) | C3—C4—C13—F3 | 127.75 (17) |
C10—C1—C6—C5 | 149.84 (17) | C9—C4—C13—F3 | −54.0 (2) |
C14—C1—C6—C5 | 24.6 (3) | C3—C4—C13—F2 | −113.45 (18) |
C10—C1—C6—C7 | −32.5 (2) | C9—C4—C13—F2 | 64.8 (2) |
C14—C1—C6—C7 | −157.71 (18) | O1—C8—N1—C7 | 179.68 (14) |
C5—C6—C7—N1 | 3.8 (2) | C9—C8—N1—C7 | −1.0 (2) |
C1—C6—C7—N1 | −174.01 (16) | N2—C7—N1—C8 | 177.59 (14) |
C5—C6—C7—N2 | −175.99 (15) | C6—C7—N1—C8 | −2.2 (2) |
C1—C6—C7—N2 | 6.2 (3) | C6—C7—N2—C12 | −168.50 (19) |
N1—C8—C9—C5 | 2.4 (2) | N1—C7—N2—C11 | 178.78 (16) |
O1—C8—C9—C5 | −178.35 (14) | C15—C11—N2—C7 | 147.17 (18) |
N1—C8—C9—C4 | −178.67 (15) | C10—C11—N2—C7 | 23.8 (2) |
O1—C8—C9—C4 | 0.6 (2) | C15—C11—N2—C12 | −45.5 (3) |
C6—C5—C9—C8 | −0.6 (2) | C10—C11—N2—C12 | −168.90 (19) |
C6—C5—C9—C4 | −179.36 (16) | N1—C8—O1—C2 | 179.03 (14) |
C3—C4—C9—C8 | −0.1 (2) | C9—C8—O1—C2 | −0.3 (2) |
C13—C4—C9—C8 | −178.40 (15) | O2—C2—O1—C8 | 178.48 (15) |
C3—C4—C9—C5 | 178.59 (16) | C3—C2—O1—C8 | −0.4 (2) |
C17H19F3N2O | F(000) = 680 |
Mr = 324.34 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9368 reflections |
a = 12.1853 (5) Å | θ = 1.0–27.5° |
b = 12.2242 (4) Å | µ = 0.11 mm−1 |
c = 10.6361 (3) Å | T = 180 K |
β = 93.4529 (11)° | Unknown, yellow |
V = 1581.43 (9) Å3 | 0.32 × 0.16 × 0.12 mm |
Z = 4 |
KappaCCD diffractometer | 3601 independent reflections |
Radiation source: fine-focus sealed tube | 2179 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 3.7° |
CCD scans | h = −15→15 |
Absorption correction: multi-scan (Blessing, 1997) | k = −15→15 |
Tmin = 0.943, Tmax = 0.989 | l = −13→13 |
14885 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3 |
3601 reflections | (Δ/σ)max < 0.001 |
284 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C17H19F3N2O | V = 1581.43 (9) Å3 |
Mr = 324.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1853 (5) Å | µ = 0.11 mm−1 |
b = 12.2242 (4) Å | T = 180 K |
c = 10.6361 (3) Å | 0.32 × 0.16 × 0.12 mm |
β = 93.4529 (11)° |
KappaCCD diffractometer | 3601 independent reflections |
Absorption correction: multi-scan (Blessing, 1997) | 2179 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.989 | Rint = 0.062 |
14885 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.00 | Δρmax = 0.22 e Å−3 |
3601 reflections | Δρmin = −0.28 e Å−3 |
284 parameters |
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 | 0.37858 (15) | 0.10863 (13) | 0.19150 (16) | 0.0341 (4) | |
C2 | 0.05239 (15) | −0.19513 (14) | −0.18187 (16) | 0.0341 (4) | |
C3 | 0.11890 (15) | −0.26681 (14) | −0.10184 (16) | 0.0345 (4) | |
C4 | 0.19407 (14) | −0.22888 (12) | −0.01473 (15) | 0.0290 (4) | |
C5 | 0.28973 (14) | −0.06881 (13) | 0.09354 (16) | 0.0296 (4) | |
C6 | 0.29987 (14) | 0.04135 (13) | 0.10744 (15) | 0.0293 (4) | |
C7 | 0.23139 (14) | 0.11227 (12) | 0.03302 (15) | 0.0292 (4) | |
C8 | 0.15392 (15) | 0.07277 (13) | −0.05515 (16) | 0.0303 (4) | |
C9 | 0.14378 (14) | −0.04151 (12) | −0.07069 (14) | 0.0272 (4) | |
C10 | 0.21080 (14) | −0.11406 (12) | 0.00472 (15) | 0.0274 (4) | |
C11 | 0.31771 (17) | 0.22020 (14) | 0.18754 (18) | 0.0385 (5) | |
C12 | 0.17909 (18) | 0.30711 (15) | 0.0320 (2) | 0.0398 (5) | |
C13 | −0.00241 (18) | −0.00971 (16) | −0.2378 (2) | 0.0392 (5) | |
C14 | 0.26336 (16) | −0.31053 (13) | 0.05997 (17) | 0.0360 (4) | |
C15 | 0.3930 (2) | 0.06468 (18) | 0.32525 (19) | 0.0451 (5) | |
C16 | 0.48967 (18) | 0.11344 (19) | 0.1319 (2) | 0.0467 (5) | |
C17 | 0.3878 (2) | 0.32150 (17) | 0.2094 (3) | 0.0542 (6) | |
F1 | 0.26308 (9) | −0.29590 (8) | 0.18444 (9) | 0.0456 (3) | |
F2 | 0.36909 (9) | −0.30578 (9) | 0.03196 (11) | 0.0535 (3) | |
F3 | 0.23105 (10) | −0.41370 (7) | 0.03869 (11) | 0.0567 (4) | |
H3 | 0.1077 (15) | −0.3436 (14) | −0.1152 (15) | 0.037 (5)* | |
H5 | 0.3379 (15) | −0.1191 (13) | 0.1455 (15) | 0.032 (4)* | |
H8 | 0.1097 (15) | 0.1192 (13) | −0.1019 (16) | 0.032 (5)* | |
H11 | 0.2583 (17) | 0.2200 (14) | 0.2547 (18) | 0.047 (5)* | |
H12A | 0.1440 (18) | 0.3053 (17) | −0.054 (2) | 0.059 (6)* | |
H13A | −0.0493 (18) | −0.0488 (17) | −0.2926 (19) | 0.056 (6)* | |
H15A | 0.4327 (18) | 0.1160 (16) | 0.381 (2) | 0.055 (6)* | |
H16A | 0.4774 (17) | 0.1451 (15) | 0.045 (2) | 0.052 (6)* | |
H17A | 0.431 (2) | 0.3160 (17) | 0.292 (2) | 0.067 (7)* | |
H12B | 0.123 (2) | 0.3111 (18) | 0.096 (2) | 0.079 (8)* | |
H13B | −0.0482 (19) | 0.0350 (17) | −0.186 (2) | 0.063 (7)* | |
H15B | 0.321 (2) | 0.0536 (17) | 0.3611 (19) | 0.064 (7)* | |
H16B | 0.5442 (18) | 0.1583 (16) | 0.1821 (18) | 0.056 (6)* | |
H17B | 0.341 (2) | 0.3878 (18) | 0.215 (2) | 0.070 (7)* | |
H12C | 0.2183 (18) | 0.3748 (18) | 0.0362 (19) | 0.057 (6)* | |
H13C | 0.043 (2) | 0.0356 (19) | −0.285 (2) | 0.073 (7)* | |
H15C | 0.4393 (19) | −0.0050 (19) | 0.3299 (19) | 0.065 (6)* | |
H16C | 0.5235 (18) | 0.0373 (18) | 0.1283 (19) | 0.058 (6)* | |
H17C | 0.438 (2) | 0.3315 (17) | 0.139 (2) | 0.065 (7)* | |
N1 | 0.06657 (11) | −0.08403 (10) | −0.15980 (12) | 0.0298 (3) | |
N2 | 0.25658 (12) | 0.21959 (10) | 0.06281 (13) | 0.0343 (4) | |
O2 | −0.01422 (11) | −0.22857 (10) | −0.26542 (12) | 0.0471 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0344 (11) | 0.0314 (9) | 0.0358 (10) | −0.0055 (8) | −0.0025 (8) | −0.0057 (7) |
C2 | 0.0367 (11) | 0.0281 (9) | 0.0367 (9) | −0.0076 (7) | −0.0035 (8) | −0.0020 (7) |
C3 | 0.0419 (12) | 0.0223 (9) | 0.0390 (10) | −0.0050 (8) | −0.0021 (8) | −0.0018 (7) |
C4 | 0.0312 (10) | 0.0240 (8) | 0.0319 (9) | −0.0006 (7) | 0.0018 (8) | 0.0017 (7) |
C5 | 0.0279 (10) | 0.0267 (9) | 0.0337 (9) | 0.0021 (7) | −0.0028 (8) | 0.0002 (7) |
C6 | 0.0272 (10) | 0.0272 (9) | 0.0333 (9) | −0.0023 (7) | −0.0006 (7) | −0.0038 (7) |
C7 | 0.0320 (10) | 0.0234 (8) | 0.0323 (9) | −0.0033 (7) | 0.0025 (8) | −0.0026 (7) |
C8 | 0.0323 (10) | 0.0248 (8) | 0.0332 (9) | 0.0008 (7) | −0.0022 (8) | 0.0013 (7) |
C9 | 0.0278 (10) | 0.0244 (9) | 0.0292 (8) | −0.0021 (7) | −0.0002 (7) | −0.0015 (7) |
C10 | 0.0282 (9) | 0.0221 (8) | 0.0321 (9) | 0.0005 (7) | 0.0024 (7) | −0.0023 (7) |
C11 | 0.0455 (12) | 0.0305 (10) | 0.0386 (10) | −0.0055 (8) | −0.0043 (9) | −0.0069 (8) |
C12 | 0.0467 (13) | 0.0227 (10) | 0.0500 (13) | −0.0006 (8) | 0.0016 (11) | 0.0010 (8) |
C13 | 0.0414 (12) | 0.0320 (10) | 0.0425 (11) | −0.0003 (9) | −0.0130 (10) | 0.0033 (9) |
C14 | 0.0400 (12) | 0.0266 (10) | 0.0412 (10) | −0.0011 (8) | 0.0009 (8) | −0.0003 (8) |
C15 | 0.0515 (14) | 0.0441 (12) | 0.0385 (11) | −0.0039 (11) | −0.0075 (10) | −0.0044 (9) |
C16 | 0.0371 (12) | 0.0510 (13) | 0.0512 (13) | −0.0104 (10) | −0.0025 (10) | −0.0085 (11) |
C17 | 0.0670 (17) | 0.0357 (12) | 0.0579 (15) | −0.0130 (11) | −0.0123 (13) | −0.0090 (10) |
F1 | 0.0558 (8) | 0.0426 (6) | 0.0375 (6) | 0.0063 (5) | −0.0037 (5) | 0.0076 (5) |
F2 | 0.0396 (7) | 0.0523 (7) | 0.0693 (8) | 0.0155 (5) | 0.0086 (6) | 0.0117 (6) |
F3 | 0.0759 (9) | 0.0204 (5) | 0.0711 (8) | 0.0004 (5) | −0.0183 (6) | 0.0024 (5) |
N1 | 0.0311 (8) | 0.0248 (7) | 0.0327 (8) | −0.0016 (6) | −0.0052 (6) | 0.0018 (6) |
N2 | 0.0427 (10) | 0.0217 (7) | 0.0380 (8) | −0.0029 (6) | −0.0024 (7) | −0.0024 (6) |
O2 | 0.0557 (9) | 0.0343 (7) | 0.0485 (8) | −0.0106 (6) | −0.0194 (7) | −0.0018 (6) |
C6—C7 | 1.412 (2) | C11—C17 | 1.514 (3) |
C7—C8 | 1.377 (2) | C11—H11 | 1.05 (2) |
C8—C9 | 1.411 (2) | C12—N2 | 1.451 (2) |
C9—C10 | 1.420 (2) | C12—H12A | 0.98 (2) |
C5—C10 | 1.419 (2) | C12—H12B | 0.99 (3) |
C5—C6 | 1.359 (2) | C12—H12C | 0.95 (2) |
C9—N1 | 1.395 (2) | C13—N1 | 1.462 (2) |
C2—N1 | 1.387 (2) | C13—H13A | 0.92 (2) |
C2—C3 | 1.437 (2) | C13—H13B | 0.97 (2) |
C3—C4 | 1.345 (2) | C13—H13C | 0.95 (2) |
C4—C10 | 1.432 (2) | C14—F1 | 1.336 (2) |
C2—O2 | 1.236 (2) | C14—F3 | 1.3365 (19) |
C7—N2 | 1.380 (2) | C14—F2 | 1.341 (2) |
C1—C6 | 1.514 (2) | C15—H15A | 0.97 (2) |
C1—C15 | 1.521 (3) | C15—H15B | 0.98 (2) |
C1—C16 | 1.530 (3) | C15—H15C | 1.02 (2) |
C1—C11 | 1.552 (2) | C16—H16A | 1.00 (2) |
C3—H3 | 0.957 (17) | C16—H16B | 0.99 (2) |
C4—C14 | 1.503 (2) | C16—H16C | 1.02 (2) |
C5—H5 | 0.994 (17) | C17—H17A | 1.01 (2) |
C8—H8 | 0.910 (18) | C17—H17B | 0.99 (2) |
C11—N2 | 1.482 (2) | C17—H17C | 1.00 (2) |
C6—C1—C15 | 113.20 (15) | H12A—C12—H12B | 111 (2) |
C6—C1—C16 | 108.74 (14) | N2—C12—H12C | 108.2 (13) |
C15—C1—C16 | 110.19 (17) | H12A—C12—H12C | 104.5 (17) |
C6—C1—C11 | 100.18 (14) | H12B—C12—H12C | 106.8 (18) |
C15—C1—C11 | 111.36 (16) | N1—C13—H13A | 110.5 (13) |
C16—C1—C11 | 112.86 (16) | N1—C13—H13B | 110.9 (12) |
O2—C2—N1 | 120.99 (16) | H13A—C13—H13B | 107.0 (18) |
O2—C2—C3 | 123.12 (15) | N1—C13—H13C | 109.3 (14) |
N1—C2—C3 | 115.89 (15) | H13A—C13—H13C | 109.0 (18) |
C4—C3—C2 | 122.27 (15) | H13B—C13—H13C | 110.1 (19) |
C4—C3—H3 | 121.7 (11) | F1—C14—F3 | 106.01 (13) |
C2—C3—H3 | 116.0 (11) | F1—C14—F2 | 105.91 (15) |
C3—C4—C10 | 121.50 (15) | F3—C14—F2 | 106.29 (14) |
C3—C4—C14 | 118.20 (14) | F1—C14—C4 | 113.58 (14) |
C10—C4—C14 | 120.27 (14) | F3—C14—C4 | 112.75 (15) |
C6—C5—C10 | 120.80 (16) | F2—C14—C4 | 111.74 (14) |
C6—C5—H5 | 120.3 (9) | C1—C15—H15A | 111.7 (12) |
C10—C5—H5 | 118.9 (9) | C1—C15—H15B | 110.9 (12) |
C5—C6—C7 | 120.01 (15) | H15A—C15—H15B | 105.8 (17) |
C5—C6—C1 | 130.74 (15) | C1—C15—H15C | 111.9 (12) |
C7—C6—C1 | 109.22 (13) | H15A—C15—H15C | 104.8 (17) |
C8—C7—N2 | 128.57 (15) | H15B—C15—H15C | 111.5 (17) |
C8—C7—C6 | 121.60 (14) | C1—C16—H16A | 108.0 (12) |
N2—C7—C6 | 109.83 (14) | C1—C16—H16B | 112.3 (12) |
C7—C8—C9 | 118.58 (16) | H16A—C16—H16B | 109.8 (16) |
C7—C8—H8 | 120.8 (11) | C1—C16—H16C | 110.5 (12) |
C9—C8—H8 | 120.6 (11) | H16A—C16—H16C | 110.8 (16) |
N1—C9—C8 | 119.94 (14) | H16B—C16—H16C | 105.4 (17) |
N1—C9—C10 | 119.49 (13) | C11—C17—H17A | 110.1 (12) |
C8—C9—C10 | 120.57 (15) | C11—C17—H17B | 111.1 (14) |
C5—C10—C9 | 118.43 (14) | H17A—C17—H17B | 105.8 (18) |
C5—C10—C4 | 124.28 (15) | C11—C17—H17C | 110.2 (13) |
C9—C10—C4 | 117.29 (14) | H17A—C17—H17C | 110.8 (19) |
N2—C11—C17 | 112.94 (16) | H17B—C17—H17C | 108.7 (17) |
N2—C11—C1 | 103.51 (13) | C2—N1—C9 | 123.48 (14) |
C17—C11—C1 | 116.77 (18) | C2—N1—C13 | 116.81 (14) |
N2—C11—H11 | 106.2 (10) | C9—N1—C13 | 119.69 (13) |
C17—C11—H11 | 107.7 (10) | C7—N2—C12 | 121.09 (15) |
C1—C11—H11 | 109.2 (10) | C7—N2—C11 | 107.65 (13) |
N2—C12—H12A | 115.7 (13) | C12—N2—C11 | 118.90 (14) |
N2—C12—H12B | 110.4 (14) | ||
C6—C7—N2—C11 | −18.60 (19) | C14—C4—C10—C5 | −0.9 (2) |
C8—C7—N2—C12 | 20.5 (3) | C3—C4—C10—C9 | 0.8 (2) |
O2—C2—C3—C4 | 177.31 (18) | C14—C4—C10—C9 | 178.89 (15) |
N1—C2—C3—C4 | −3.0 (3) | C6—C1—C11—N2 | −28.76 (17) |
C2—C3—C4—C10 | 1.1 (3) | C15—C1—C11—N2 | −148.76 (16) |
C2—C3—C4—C14 | −177.06 (16) | C16—C1—C11—N2 | 86.70 (18) |
C10—C5—C6—C7 | 0.0 (2) | C6—C1—C11—C17 | −153.51 (17) |
C10—C5—C6—C1 | −178.02 (16) | C15—C1—C11—C17 | 86.5 (2) |
C15—C1—C6—C5 | −44.0 (3) | C16—C1—C11—C17 | −38.1 (2) |
C16—C1—C6—C5 | 78.8 (2) | C3—C4—C14—F1 | −127.99 (17) |
C11—C1—C6—C5 | −162.70 (18) | C10—C4—C14—F1 | 53.8 (2) |
C15—C1—C6—C7 | 137.77 (17) | C3—C4—C14—F3 | −7.4 (2) |
C16—C1—C6—C7 | −99.41 (17) | C10—C4—C14—F3 | 174.45 (15) |
C11—C1—C6—C7 | 19.12 (17) | C3—C4—C14—F2 | 112.27 (18) |
C5—C6—C7—C8 | −0.4 (2) | C10—C4—C14—F2 | −65.9 (2) |
C1—C6—C7—C8 | 177.98 (15) | O2—C2—N1—C9 | −177.10 (16) |
C5—C6—C7—N2 | −179.73 (14) | C3—C2—N1—C9 | 3.2 (2) |
C1—C6—C7—N2 | −1.32 (18) | O2—C2—N1—C13 | 1.3 (2) |
N2—C7—C8—C9 | 179.02 (16) | C3—C2—N1—C13 | −178.38 (16) |
C6—C7—C8—C9 | −0.1 (2) | C8—C9—N1—C2 | 179.20 (15) |
C7—C8—C9—N1 | −179.58 (15) | C10—C9—N1—C2 | −1.5 (2) |
C7—C8—C9—C10 | 1.1 (2) | C8—C9—N1—C13 | 0.8 (2) |
C6—C5—C10—C9 | 0.9 (2) | C10—C9—N1—C13 | −179.86 (16) |
C6—C5—C10—C4 | −179.28 (16) | C6—C7—N2—C12 | −160.24 (16) |
N1—C9—C10—C5 | 179.18 (14) | C8—C7—N2—C11 | 162.17 (17) |
C8—C9—C10—C5 | −1.5 (2) | C17—C11—N2—C7 | 157.40 (18) |
N1—C9—C10—C4 | −0.6 (2) | C1—C11—N2—C7 | 30.20 (18) |
C8—C9—C10—C4 | 178.70 (15) | C17—C11—N2—C12 | −60.0 (3) |
C3—C4—C10—C5 | −179.00 (16) | C1—C11—N2—C12 | 172.83 (16) |
Experimental details
(ld425) | (ld489) | (ld473) | |
Crystal data | |||
Chemical formula | C13H14N2O3 | C15H15F3N2O2 | C17H19F3N2O |
Mr | 246.26 | 312.29 | 324.34 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 180 | 180 | 180 |
a, b, c (Å) | 7.061 (5), 24.489 (15), 13.930 (9) | 8.9941 (5), 11.2954 (6), 14.3536 (9) | 12.1853 (5), 12.2242 (4), 10.6361 (3) |
β (°) | 103.481 (8) | 102.537 (3) | 93.4529 (11) |
V (Å3) | 2342 (3) | 1423.44 (14) | 1581.43 (9) |
Z | 8 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.12 | 0.11 |
Crystal size (mm) | 0.56 × 0.28 × 0.11 | 0.42 × 0.22 × 0.14 | 0.32 × 0.16 × 0.12 |
Data collection | |||
Diffractometer | Rigaku CrystalClear-SM Expert 2.0 r4 diffractometer | KappaCCD diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 | Multi-scan (Blessing, 1997) | Multi-scan (Blessing, 1997) |
Tmin, Tmax | 0.973, 1.028 | 0.958, 0.998 | 0.943, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14043, 5763, 4634 | 7357, 3199, 2235 | 14885, 3601, 2179 |
Rint | 0.077 | 0.032 | 0.062 |
(sin θ/λ)max (Å−1) | 0.667 | 0.647 | 0.649 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.158, 1.13 | 0.048, 0.127, 1.04 | 0.048, 0.123, 1.00 |
No. of reflections | 5763 | 3199 | 3601 |
No. of parameters | 437 | 259 | 284 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.31, −0.49 | 0.31, −0.25 | 0.22, −0.28 |
Computer programs: Rigaku CrystalClear-SM Expert 2.0 r4, COLLECT (Nonius BV, 1998), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), publCIF (Westrip, 2010).
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