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The molecular structures of three compounds, LD 425 (C13H14N2O3) (1), LD 489 (C15H15F3N2O2) (2) and LD 473 (C17H19F3N2O) (3), are determined by single-crystal X-ray diffraction (XRD) at 180 K. Azacoumarins (1) and (2) possess para-quinoidal bond-length patterns in their benzene rings due to intramolecular charge transfer (ICT) from these rings to the adjoining rings. In contrast, substitution of O with N within the coumarin heterocycle, to form a 2-quinolone, results in the suppression of this ICT effect. Instead, charge transfer within the heterocycle is shown to become more pronounced. Resonance theory is employed to discuss these bond pattern differences and characteristic spectral blue shifts in relation to their coumarin analogues. The application of this theory offers an intuitive understanding of the structure-property relationships in azacoumarins and 2-quinolones which is further supported by quantum chemical calculations. Such an understanding is important for recognizing ICT mechanisms in these compounds which can then be used to facilitate the molecular design of new laser dyes with the desired spectral shifts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111037311/bk5105sup1.cif
Contains datablocks ld425, ld489, ld473, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037311/bk5105ld425sup2.hkl
Contains datablock ld425

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037311/bk5105ld489sup3.hkl
Contains datablock ld489

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111037311/bk5105ld473sup4.hkl
Contains datablock ld473

CCDC references: 861008; 861009; 861010

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(ld425) top
Crystal data top
C13H14N2O3F(000) = 1040
Mr = 246.26Dx = 1.397 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6908 reflections
a = 7.061 (5) Åθ = 1.7–33.1°
b = 24.489 (15) ŵ = 0.10 mm1
c = 13.930 (9) ÅT = 180 K
β = 103.481 (8)°Platelet, colorless
V = 2342 (3) Å30.56 × 0.28 × 0.11 mm
Z = 8
Data collection top
Rigaku CrystalClear-SM Expert 2.0 r4
diffractometer
5763 independent reflections
Radiation source: fine-focus sealed tube4634 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
Detector resolution: 28.5714 pixels mm-1θmax = 28.3°, θmin = 2.9°
profile data from ω–scansh = 99
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 = 3232
Tmin = 0.973, Tmax = 1.028l = 1818
14043 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158All 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 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
C13H14N2O3V = 2342 (3) Å3
Mr = 246.26Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.061 (5) ŵ = 0.10 mm1
b = 24.489 (15) ÅT = 180 K
c = 13.930 (9) Å0.56 × 0.28 × 0.11 mm
β = 103.481 (8)°
Data collection top
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 = 1.028Rint = 0.077
14043 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.158All H-atom parameters refined
S = 1.13Δρmax = 0.31 e Å3
5763 reflectionsΔρmin = 0.49 e Å3
437 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9461 (3)0.32749 (8)0.51150 (14)0.0365 (4)
C21.0239 (3)0.31857 (6)0.79281 (13)0.0289 (4)
C30.9999 (3)0.33907 (6)0.69354 (13)0.0285 (3)
C40.9731 (3)0.30570 (6)0.61449 (12)0.0269 (3)
C50.9466 (3)0.20756 (7)0.55654 (13)0.0289 (3)
C60.9456 (3)0.15300 (7)0.58036 (13)0.0297 (4)
C70.9653 (3)0.13818 (6)0.68034 (13)0.0274 (3)
C80.9912 (2)0.22765 (6)0.72641 (12)0.0253 (3)
C90.9689 (3)0.24746 (6)0.63058 (12)0.0254 (3)
C100.8563 (3)0.00960 (7)0.67249 (16)0.0375 (4)
C110.9627 (3)0.03917 (7)0.64244 (15)0.0342 (4)
C121.0232 (3)0.07002 (7)0.81380 (14)0.0368 (4)
C130.9132 (4)0.02028 (7)0.83592 (16)0.0392 (4)
N10.9903 (2)0.17579 (5)0.75302 (10)0.0282 (3)
N20.9565 (2)0.08469 (5)0.70933 (11)0.0312 (3)
O11.0178 (2)0.26266 (4)0.80581 (9)0.0303 (3)
O21.0474 (2)0.34628 (5)0.86719 (9)0.0387 (3)
O30.9335 (2)0.02438 (5)0.77298 (11)0.0392 (3)
H31.007 (3)0.3794 (9)0.6895 (15)0.033 (5)*
H50.932 (3)0.2178 (9)0.4859 (16)0.040 (6)*
H60.933 (4)0.1269 (10)0.5321 (17)0.044 (6)*
H10A0.718 (4)0.0011 (9)0.6641 (16)0.040 (6)*
H11A0.894 (4)0.0492 (9)0.5699 (17)0.041 (6)*
H12A0.994 (4)0.1002 (10)0.8522 (18)0.049 (7)*
H13A0.767 (4)0.0294 (9)0.8267 (17)0.047 (7)*
H10B0.873 (3)0.0424 (8)0.6329 (15)0.032 (5)*
H11B1.096 (4)0.0303 (9)0.6439 (16)0.039 (6)*
H12B1.163 (3)0.0635 (9)0.8302 (16)0.034 (6)*
H13B0.975 (3)0.0070 (9)0.9046 (17)0.042 (6)*
H1A0.813 (4)0.3148 (10)0.4693 (17)0.052 (7)*
H1B0.952 (4)0.3694 (9)0.5139 (16)0.043 (6)*
H1C1.044 (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)*
H10C0.289 (4)0.9457 (9)0.8536 (17)0.044 (6)*
H11C0.554 (4)0.8922 (9)0.9401 (17)0.040 (6)*
H12C0.419 (4)0.8540 (9)0.6579 (16)0.043 (6)*
H13C0.215 (3)0.9233 (9)0.6834 (16)0.037 (6)*
H10D0.482 (3)0.9822 (9)0.8955 (16)0.039 (6)*
H11D0.696 (4)0.9148 (10)0.8762 (17)0.046 (6)*
H12D0.616 (3)0.8896 (9)0.6928 (15)0.032 (5)*
H13D0.366 (4)0.9486 (9)0.6128 (17)0.044 (6)*
H1D0.459 (4)0.6172 (9)0.9843 (17)0.043 (6)*
H1E0.588 (4)0.5682 (10)0.9486 (17)0.044 (6)*
H1F0.684 (4)0.6220 (9)1.0033 (17)0.041 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0478 (12)0.0315 (8)0.0297 (9)0.0035 (8)0.0077 (8)0.0065 (7)
C20.0347 (9)0.0217 (7)0.0310 (8)0.0027 (6)0.0094 (7)0.0014 (6)
C30.0322 (9)0.0226 (7)0.0319 (8)0.0007 (6)0.0098 (7)0.0016 (6)
C40.0263 (8)0.0249 (7)0.0297 (8)0.0020 (6)0.0071 (7)0.0039 (6)
C50.0319 (9)0.0269 (7)0.0289 (8)0.0004 (6)0.0087 (7)0.0021 (6)
C60.0340 (9)0.0254 (7)0.0312 (8)0.0011 (7)0.0102 (7)0.0049 (6)
C70.0285 (8)0.0221 (7)0.0331 (8)0.0003 (6)0.0104 (7)0.0011 (6)
C80.0267 (8)0.0232 (7)0.0273 (8)0.0003 (6)0.0086 (6)0.0009 (6)
C90.0264 (8)0.0232 (7)0.0266 (8)0.0009 (6)0.0060 (6)0.0000 (6)
C100.0377 (10)0.0242 (7)0.0496 (11)0.0027 (7)0.0081 (9)0.0028 (7)
C110.0408 (10)0.0227 (7)0.0417 (10)0.0007 (7)0.0146 (8)0.0053 (7)
C120.0506 (12)0.0240 (7)0.0360 (9)0.0043 (8)0.0105 (9)0.0016 (7)
C130.0494 (12)0.0257 (8)0.0457 (11)0.0010 (8)0.0175 (10)0.0033 (7)
N10.0339 (8)0.0213 (6)0.0304 (7)0.0009 (5)0.0097 (6)0.0005 (5)
N20.0403 (9)0.0204 (6)0.0341 (7)0.0012 (6)0.0110 (7)0.0011 (5)
O10.0444 (8)0.0208 (5)0.0265 (6)0.0017 (5)0.0100 (5)0.0002 (4)
O20.0597 (10)0.0257 (5)0.0324 (7)0.0051 (6)0.0142 (7)0.0041 (5)
O30.0437 (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)
Geometric parameters (Å, º) top
C6—C71.414 (3)C10—C111.521 (3)
C7—N11.350 (2)C10—H10A0.98 (2)
C8—N11.324 (2)C10—H10B1.00 (2)
C8—C91.394 (2)C11—N21.460 (2)
C5—C91.403 (2)C11—H11A1.04 (2)
C5—C61.377 (2)C11—H11B0.96 (2)
C8—O11.377 (2)C12—N21.466 (2)
C2—O11.383 (2)C12—C131.514 (3)
C2—C31.444 (2)C12—H12A0.96 (3)
C3—C41.349 (2)C12—H12B0.98 (2)
C4—C91.445 (2)C13—O31.430 (2)
C2—O21.217 (2)C13—H13A1.03 (3)
C6'—C7'1.419 (2)C13—H13B1.01 (2)
C7'—N1'1.349 (2)C1'—C4'1.501 (2)
C8'—N1'1.322 (2)C1'—H1D1.00 (3)
C8'—C9'1.398 (2)C1'—H1E1.00 (2)
C5'—C9'1.407 (2)C1'—H1F0.97 (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'—H10C1.04 (3)
C2'—O2'1.214 (2)C10'—H10D0.95 (2)
C7—N21.376 (2)C11'—N2'1.464 (2)
C7'—N2'1.367 (2)C11'—H11C0.95 (2)
C1—C41.501 (2)C11'—H11D1.00 (3)
C1—H1A1.03 (3)C12'—N2'1.468 (2)
C1—H1B1.03 (2)C12'—C13'1.517 (3)
C1—H1C0.96 (3)C12'—H12C0.93 (2)
C3—H30.99 (2)C12'—H12D1.00 (2)
C5—H51.00 (2)C13'—O3'1.428 (2)
C6—H60.92 (2)C13'—H13C1.02 (2)
C10—O31.426 (3)C13'—H13D1.06 (2)
C4—C1—H1A109.4 (13)C4'—C1'—H1D109.5 (13)
C4—C1—H1B109.2 (12)C4'—C1'—H1E111.5 (13)
H1A—C1—H1B109.9 (19)H1D—C1'—H1E111.6 (19)
C4—C1—H1C110.0 (15)C4'—C1'—H1F111.8 (14)
H1A—C1—H1C107.0 (19)H1D—C1'—H1F104.0 (19)
H1B—C1—H1C111 (2)H1E—C1'—H1F108.2 (19)
O2—C2—O1116.28 (15)O2'—C2'—O1'116.13 (16)
O2—C2—C3125.72 (16)O2'—C2'—C3'126.42 (16)
O1—C2—C3118.00 (14)O1'—C2'—C3'117.45 (15)
C4—C3—C2122.28 (15)C4'—C3'—C2'122.42 (15)
C4—C3—H3123.8 (12)C4'—C3'—H3'122.4 (13)
C2—C3—H3113.9 (12)C2'—C3'—H3'115.1 (13)
C3—C4—C9118.40 (15)C3'—C4'—C9'119.01 (15)
C3—C4—C1121.83 (16)C3'—C4'—C1'121.19 (15)
C9—C4—C1119.77 (15)C9'—C4'—C1'119.80 (15)
C6—C5—C9120.31 (16)C6'—C5'—C9'120.66 (16)
C6—C5—H5118.5 (13)C6'—C5'—H5'118.0 (12)
C9—C5—H5121.2 (13)C9'—C5'—H5'121.3 (12)
C5—C6—C7118.78 (15)C5'—C6'—C7'118.61 (16)
C5—C6—H6120.3 (15)C5'—C6'—H6'120.6 (13)
C7—C6—H6120.9 (15)C7'—C6'—H6'120.7 (13)
N1—C7—N2115.86 (15)N1'—C7'—N2'115.96 (15)
N1—C7—C6121.96 (15)N1'—C7'—C6'121.83 (15)
N2—C7—C6122.17 (15)N2'—C7'—C6'122.17 (15)
N1—C8—O1112.40 (14)N1'—C8'—O1'112.35 (15)
N1—C8—C9126.53 (15)N1'—C8'—C9'126.23 (15)
O1—C8—C9121.07 (14)O1'—C8'—C9'121.42 (15)
C8—C9—C5115.46 (15)C8'—C9'—C5'115.30 (15)
C8—C9—C4119.34 (15)C8'—C9'—C4'118.37 (15)
C5—C9—C4125.20 (15)C5'—C9'—C4'126.31 (15)
O3—C10—C11111.69 (16)O3'—C10'—C11'111.85 (16)
O3—C10—H10A108.2 (13)O3'—C10'—H10C108.4 (13)
C11—C10—H10A110.2 (13)C11'—C10'—H10C110.6 (13)
O3—C10—H10B105.7 (12)O3'—C10'—H10D108.2 (14)
C11—C10—H10B110.4 (12)C11'—C10'—H10D108.1 (14)
H10A—C10—H10B110.5 (18)H10C—C10'—H10D109.7 (19)
N2—C11—C10109.48 (16)N2'—C11'—C10'109.27 (17)
N2—C11—H11A111.1 (13)N2'—C11'—H11C112.2 (14)
C10—C11—H11A107.6 (13)C10'—C11'—H11C109.1 (14)
N2—C11—H11B109.5 (13)N2'—C11'—H11D109.1 (14)
C10—C11—H11B111.1 (14)C10'—C11'—H11D108.4 (14)
H11A—C11—H11B107.9 (18)H11C—C11'—H11D108.7 (19)
N2—C12—C13109.75 (17)N2'—C12'—C13'109.14 (16)
N2—C12—H12A107.7 (15)N2'—C12'—H12C106.7 (14)
C13—C12—H12A108.6 (15)C13'—C12'—H12C108.5 (15)
N2—C12—H12B110.3 (13)N2'—C12'—H12D108.6 (12)
C13—C12—H12B111.1 (13)C13'—C12'—H12D110.5 (12)
H12A—C12—H12B109 (2)H12C—C12'—H12D113.3 (19)
O3—C13—C12111.18 (17)O3'—C13'—C12'111.63 (17)
O3—C13—H13A109.1 (13)O3'—C13'—H13C109.3 (12)
C12—C13—H13A110.2 (13)C12'—C13'—H13C110.6 (12)
O3—C13—H13B104.6 (13)O3'—C13'—H13D105.7 (12)
C12—C13—H13B108.8 (13)C12'—C13'—H13D107.5 (13)
H13A—C13—H13B112.8 (19)H13C—C13'—H13D112.1 (18)
C8—N1—C7116.94 (15)C8'—N1'—C7'117.35 (15)
C7—N2—C11121.95 (16)C7'—N2'—C11'122.71 (16)
C7—N2—C12119.91 (14)C7'—N2'—C12'119.85 (15)
C11—N2—C12113.31 (15)C11'—N2'—C12'113.14 (14)
C8—O1—C2120.91 (13)C8'—O1'—C2'121.32 (14)
C10—O3—C13109.75 (15)C13'—O3'—C10'109.91 (14)
C6—C7—N2—C1111.6 (3)C11—C10—O3—C1360.5 (2)
N1—C7—N2—C1215.8 (3)C12—C13—O3—C1060.7 (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—C4179.52 (19)C2'—C3'—C4'—C9'1.2 (3)
O1—C2—C3—C40.3 (3)C2'—C3'—C4'—C1'177.93 (18)
C2—C3—C4—C90.1 (3)C9'—C5'—C6'—C7'0.4 (3)
C2—C3—C4—C1179.33 (18)C5'—C6'—C7'—N1'0.0 (3)
C9—C5—C6—C70.7 (3)C5'—C6'—C7'—N2'177.74 (18)
C5—C6—C7—N11.8 (3)N1'—C8'—C9'—C5'0.3 (3)
C5—C6—C7—N2176.89 (18)O1'—C8'—C9'—C5'179.55 (16)
N1—C8—C9—C51.1 (3)N1'—C8'—C9'—C4'179.00 (17)
O1—C8—C9—C5178.85 (15)O1'—C8'—C9'—C4'0.9 (3)
N1—C8—C9—C4179.81 (18)C6'—C5'—C9'—C8'0.5 (3)
O1—C8—C9—C40.2 (3)C6'—C5'—C9'—C4'179.12 (18)
C6—C5—C9—C80.7 (3)C3'—C4'—C9'—C8'0.0 (3)
C6—C5—C9—C4179.70 (18)C1'—C4'—C9'—C8'179.06 (16)
C3—C4—C9—C80.4 (3)C3'—C4'—C9'—C5'178.50 (17)
C1—C4—C9—C8179.06 (17)C1'—C4'—C9'—C5'2.4 (3)
C3—C4—C9—C5178.56 (17)O3'—C10'—C11'—N2'55.8 (2)
C1—C4—C9—C51.9 (3)N2'—C12'—C13'—O3'56.4 (2)
O3—C10—C11—N255.6 (2)O1'—C8'—N1'—C7'179.94 (15)
N2—C12—C13—O356.2 (2)C9'—C8'—N1'—C7'0.1 (3)
O1—C8—N1—C7179.92 (15)N2'—C7'—N1'—C8'177.62 (17)
C9—C8—N1—C70.0 (3)C6'—C7'—N1'—C8'0.2 (3)
N2—C7—N1—C8177.33 (17)N1'—C7'—N2'—C11'161.88 (18)
C6—C7—N1—C81.5 (3)C6'—C7'—N2'—C12'175.38 (17)
N1—C7—N2—C11169.55 (17)C10'—C11'—N2'—C7'150.07 (18)
C6—C7—N2—C12165.38 (18)C10'—C11'—N2'—C12'53.3 (2)
C10—C11—N2—C7152.67 (18)C13'—C12'—N2'—C7'149.04 (18)
C10—C11—N2—C1252.0 (2)C13'—C12'—N2'—C11'53.6 (2)
C13—C12—N2—C7151.52 (18)N1'—C8'—O1'—C2'179.24 (16)
C13—C12—N2—C1152.6 (2)C9'—C8'—O1'—C2'0.6 (3)
N1—C8—O1—C2179.71 (16)O2'—C2'—O1'—C8'179.05 (17)
C9—C8—O1—C20.2 (3)C3'—C2'—O1'—C8'0.4 (3)
O2—C2—O1—C8179.79 (16)C12'—C13'—O3'—C10'59.9 (2)
C3—C2—O1—C80.5 (3)C11'—C10'—O3'—C13'59.7 (2)
(ld489) top
Crystal data top
C15H15F3N2O2F(000) = 648
Mr = 312.29Dx = 1.457 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11391 reflections
a = 8.9941 (5) Åθ = 1.0–27.5°
b = 11.2954 (6) ŵ = 0.12 mm1
c = 14.3536 (9) ÅT = 180 K
β = 102.537 (3)°Unknown, orange
V = 1423.44 (14) Å30.42 × 0.22 × 0.14 mm
Z = 4
Data collection top
KappaCCD
diffractometer
3199 independent reflections
Radiation source: fine-focus sealed tube2235 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 9 pixels mm-1θmax = 27.4°, θmin = 3.8°
CCD scansh = 1111
Absorption correction: multi-scan
(Blessing, 1997)
k = 1214
Tmin = 0.958, Tmax = 0.998l = 1818
7357 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127All 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 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C15H15F3N2O2V = 1423.44 (14) Å3
Mr = 312.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.9941 (5) ŵ = 0.12 mm1
b = 11.2954 (6) ÅT = 180 K
c = 14.3536 (9) Å0.42 × 0.22 × 0.14 mm
β = 102.537 (3)°
Data collection top
KappaCCD
diffractometer
3199 independent reflections
Absorption correction: multi-scan
(Blessing, 1997)
2235 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.998Rint = 0.032
7357 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.127All H-atom parameters refined
S = 1.04Δρmax = 0.31 e Å3
3199 reflectionsΔρmin = 0.25 e Å3
259 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2477 (2)0.78948 (17)0.14985 (14)0.0391 (4)
C20.80818 (19)0.46523 (15)0.07362 (12)0.0325 (4)
C30.7898 (2)0.55964 (16)0.00517 (13)0.0330 (4)
C40.67916 (19)0.64196 (14)0.00119 (12)0.0290 (4)
C50.45757 (19)0.71682 (15)0.07080 (12)0.0300 (4)
C60.36822 (19)0.70197 (14)0.13569 (12)0.0305 (4)
C70.39573 (19)0.59913 (14)0.19546 (12)0.0294 (4)
C80.59412 (18)0.54420 (14)0.13010 (11)0.0277 (4)
C90.57626 (18)0.63679 (14)0.06469 (11)0.0269 (4)
C100.1224 (2)0.72198 (18)0.18203 (15)0.0398 (5)
C110.1795 (2)0.64828 (17)0.27112 (14)0.0390 (4)
C120.3571 (3)0.4805 (2)0.32947 (19)0.0539 (6)
C130.6682 (2)0.74157 (16)0.06926 (13)0.0378 (4)
C140.1864 (3)0.8655 (2)0.06277 (17)0.0493 (6)
C150.0514 (3)0.5755 (2)0.29548 (18)0.0517 (6)
F10.76268 (15)0.72983 (11)0.12794 (9)0.0596 (4)
F20.70122 (17)0.84548 (10)0.02397 (10)0.0636 (4)
F30.52873 (13)0.75268 (10)0.12364 (8)0.0505 (3)
H10.298 (3)0.844 (2)0.2072 (17)0.057 (6)*
H30.863 (2)0.5633 (16)0.0342 (13)0.035 (5)*
H50.440 (2)0.7812 (17)0.0288 (14)0.034 (5)*
H110.219 (2)0.705 (2)0.3271 (16)0.053 (6)*
H10A0.043 (2)0.7740 (18)0.1927 (14)0.045 (5)*
H12A0.346 (3)0.509 (3)0.395 (2)0.088 (9)*
H14A0.102 (3)0.917 (2)0.0727 (18)0.067 (7)*
H15A0.036 (3)0.628 (2)0.2940 (18)0.070 (8)*
H10B0.071 (2)0.6632 (19)0.1288 (16)0.051 (6)*
H12B0.459 (4)0.456 (3)0.328 (3)0.117 (12)*
H14B0.264 (3)0.918 (2)0.0478 (16)0.060 (7)*
H15B0.080 (3)0.537 (2)0.3598 (19)0.066 (7)*
H12C0.292 (4)0.419 (3)0.315 (2)0.092 (10)*
H14C0.139 (3)0.808 (3)0.009 (2)0.090 (9)*
H15C0.021 (3)0.507 (2)0.2430 (18)0.072 (7)*
N10.50978 (16)0.52345 (12)0.19248 (10)0.0304 (3)
N20.30719 (17)0.57286 (13)0.25804 (11)0.0357 (4)
O10.70763 (13)0.46132 (10)0.13396 (8)0.0330 (3)
O20.90560 (14)0.38881 (12)0.08503 (10)0.0439 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0448 (11)0.0323 (9)0.0432 (11)0.0059 (8)0.0163 (9)0.0015 (9)
C20.0264 (8)0.0352 (9)0.0364 (9)0.0007 (7)0.0077 (7)0.0013 (8)
C30.0280 (9)0.0392 (10)0.0339 (9)0.0017 (7)0.0112 (7)0.0001 (8)
C40.0292 (8)0.0298 (9)0.0283 (8)0.0046 (7)0.0067 (7)0.0016 (7)
C50.0346 (9)0.0242 (8)0.0320 (9)0.0011 (7)0.0088 (7)0.0018 (7)
C60.0327 (9)0.0260 (8)0.0345 (9)0.0007 (7)0.0108 (7)0.0031 (7)
C70.0320 (9)0.0299 (9)0.0273 (8)0.0041 (7)0.0091 (7)0.0036 (7)
C80.0261 (8)0.0283 (8)0.0281 (8)0.0017 (7)0.0048 (7)0.0032 (7)
C90.0284 (8)0.0261 (8)0.0262 (8)0.0018 (7)0.0056 (7)0.0004 (7)
C100.0333 (10)0.0441 (11)0.0449 (11)0.0057 (9)0.0148 (8)0.0020 (10)
C110.0384 (10)0.0423 (11)0.0401 (10)0.0010 (8)0.0167 (8)0.0058 (9)
C120.0648 (16)0.0514 (14)0.0539 (14)0.0100 (12)0.0314 (12)0.0199 (12)
C130.0406 (10)0.0370 (10)0.0400 (10)0.0007 (8)0.0177 (8)0.0036 (8)
C140.0549 (14)0.0436 (12)0.0551 (13)0.0190 (11)0.0245 (11)0.0107 (11)
C150.0439 (12)0.0638 (14)0.0524 (13)0.0065 (11)0.0215 (10)0.0027 (12)
F10.0637 (8)0.0658 (8)0.0623 (8)0.0152 (6)0.0419 (7)0.0257 (7)
F20.0959 (11)0.0341 (6)0.0653 (8)0.0164 (6)0.0275 (8)0.0021 (6)
F30.0508 (7)0.0548 (7)0.0463 (6)0.0126 (5)0.0112 (5)0.0194 (6)
N10.0319 (8)0.0296 (7)0.0313 (7)0.0006 (6)0.0100 (6)0.0020 (6)
N20.0395 (8)0.0346 (8)0.0375 (8)0.0019 (6)0.0180 (7)0.0031 (7)
O10.0302 (6)0.0335 (7)0.0369 (6)0.0061 (5)0.0110 (5)0.0066 (5)
O20.0361 (7)0.0437 (8)0.0543 (8)0.0103 (6)0.0149 (6)0.0066 (7)
Geometric parameters (Å, º) top
C6—C71.433 (2)C10—C111.519 (3)
C7—N11.343 (2)C10—H10A0.96 (2)
C8—N11.314 (2)C10—H10B1.04 (2)
C8—C91.391 (2)C11—N21.475 (2)
C5—C91.416 (2)C11—C151.517 (3)
C5—C61.366 (2)C11—H111.03 (2)
C8—O11.377 (2)C12—N21.464 (3)
C2—O11.3820 (19)C12—H12A1.01 (3)
C2—C31.435 (2)C12—H12B0.96 (4)
C3—C41.354 (2)C12—H12C0.91 (3)
C4—C91.434 (2)C13—F11.326 (2)
C2—O21.215 (2)C13—F31.332 (2)
C7—N21.356 (2)C13—F21.343 (2)
C1—C61.513 (2)C14—H14A0.99 (3)
C1—C101.514 (3)C14—H14B0.97 (2)
C1—C141.518 (3)C14—H14C1.03 (3)
C1—H11.05 (2)C15—H15A0.98 (3)
C3—H30.954 (19)C15—H15B1.00 (3)
C4—C131.502 (2)C15—H15C1.07 (3)
C5—H50.936 (19)
C6—C1—C10108.34 (15)N2—C11—C15111.58 (17)
C6—C1—C14113.68 (16)N2—C11—C10109.87 (15)
C10—C1—C14112.00 (18)C15—C11—C10110.87 (18)
C6—C1—H1107.0 (12)N2—C11—H11108.0 (12)
C10—C1—H1106.2 (12)C15—C11—H11108.1 (12)
C14—C1—H1109.2 (12)C10—C11—H11108.3 (12)
O2—C2—O1116.33 (15)N2—C12—H12A110.1 (16)
O2—C2—C3126.35 (16)N2—C12—H12B110 (2)
O1—C2—C3117.31 (14)H12A—C12—H12B113 (3)
C4—C3—C2120.92 (16)N2—C12—H12C108 (2)
C4—C3—H3122.5 (11)H12A—C12—H12C105 (2)
C2—C3—H3116.4 (11)H12B—C12—H12C110 (3)
C3—C4—C9120.98 (15)F1—C13—F3106.80 (15)
C3—C4—C13118.88 (15)F1—C13—F2106.87 (15)
C9—C4—C13120.11 (15)F3—C13—F2106.39 (15)
C6—C5—C9121.79 (16)F1—C13—C4113.30 (15)
C6—C5—H5119.6 (11)F3—C13—C4112.38 (15)
C9—C5—H5118.6 (11)F2—C13—C4110.70 (15)
C5—C6—C7117.18 (15)C1—C14—H14A111.6 (14)
C5—C6—C1123.78 (16)C1—C14—H14B112.3 (14)
C7—C6—C1118.99 (15)H14A—C14—H14B105.8 (19)
N1—C7—N2116.36 (15)C1—C14—H14C106.5 (17)
N1—C7—C6122.05 (15)H14A—C14—H14C106 (2)
N2—C7—C6121.59 (15)H14B—C14—H14C114 (2)
N1—C8—O1112.57 (14)C11—C15—H15A108.2 (15)
N1—C8—C9126.49 (15)C11—C15—H15B112.9 (14)
O1—C8—C9120.94 (14)H15A—C15—H15B109 (2)
C8—C9—C5114.60 (15)C11—C15—H15C108.6 (13)
C8—C9—C4117.62 (15)H15A—C15—H15C110 (2)
C5—C9—C4127.77 (15)H15B—C15—H15C108.1 (19)
C1—C10—C11113.25 (17)C8—N1—C7117.77 (14)
C1—C10—H10A111.8 (12)C7—N2—C12119.01 (16)
C11—C10—H10A109.1 (12)C7—N2—C11122.92 (15)
C1—C10—H10B109.7 (11)C12—N2—C11116.87 (16)
C11—C10—H10B106.4 (11)C8—O1—C2122.22 (13)
H10A—C10—H10B106.3 (17)
C6—C7—N2—C111.4 (3)C13—C4—C9—C50.3 (3)
N1—C7—N2—C1211.7 (3)C6—C1—C10—C1155.8 (2)
O2—C2—C3—C4177.94 (17)C14—C1—C10—C11178.04 (17)
O1—C2—C3—C40.8 (2)C1—C10—C11—N251.8 (2)
C2—C3—C4—C90.5 (3)C1—C10—C11—C15175.60 (18)
C2—C3—C4—C13177.75 (16)C3—C4—C13—F16.6 (2)
C9—C5—C6—C72.2 (2)C9—C4—C13—F1175.14 (15)
C9—C5—C6—C1175.43 (17)C3—C4—C13—F3127.75 (17)
C10—C1—C6—C5149.84 (17)C9—C4—C13—F354.0 (2)
C14—C1—C6—C524.6 (3)C3—C4—C13—F2113.45 (18)
C10—C1—C6—C732.5 (2)C9—C4—C13—F264.8 (2)
C14—C1—C6—C7157.71 (18)O1—C8—N1—C7179.68 (14)
C5—C6—C7—N13.8 (2)C9—C8—N1—C71.0 (2)
C1—C6—C7—N1174.01 (16)N2—C7—N1—C8177.59 (14)
C5—C6—C7—N2175.99 (15)C6—C7—N1—C82.2 (2)
C1—C6—C7—N26.2 (3)C6—C7—N2—C12168.50 (19)
N1—C8—C9—C52.4 (2)N1—C7—N2—C11178.78 (16)
O1—C8—C9—C5178.35 (14)C15—C11—N2—C7147.17 (18)
N1—C8—C9—C4178.67 (15)C10—C11—N2—C723.8 (2)
O1—C8—C9—C40.6 (2)C15—C11—N2—C1245.5 (3)
C6—C5—C9—C80.6 (2)C10—C11—N2—C12168.90 (19)
C6—C5—C9—C4179.36 (16)N1—C8—O1—C2179.03 (14)
C3—C4—C9—C80.1 (2)C9—C8—O1—C20.3 (2)
C13—C4—C9—C8178.40 (15)O2—C2—O1—C8178.48 (15)
C3—C4—C9—C5178.59 (16)C3—C2—O1—C80.4 (2)
(ld473) top
Crystal data top
C17H19F3N2OF(000) = 680
Mr = 324.34Dx = 1.362 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9368 reflections
a = 12.1853 (5) Åθ = 1.0–27.5°
b = 12.2242 (4) ŵ = 0.11 mm1
c = 10.6361 (3) ÅT = 180 K
β = 93.4529 (11)°Unknown, yellow
V = 1581.43 (9) Å30.32 × 0.16 × 0.12 mm
Z = 4
Data collection top
KappaCCD
diffractometer
3601 independent reflections
Radiation source: fine-focus sealed tube2179 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.7°
CCD scansh = 1515
Absorption correction: multi-scan
(Blessing, 1997)
k = 1515
Tmin = 0.943, Tmax = 0.989l = 1313
14885 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123All 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 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C17H19F3N2OV = 1581.43 (9) Å3
Mr = 324.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1853 (5) ŵ = 0.11 mm1
b = 12.2242 (4) ÅT = 180 K
c = 10.6361 (3) Å0.32 × 0.16 × 0.12 mm
β = 93.4529 (11)°
Data collection top
KappaCCD
diffractometer
3601 independent reflections
Absorption correction: multi-scan
(Blessing, 1997)
2179 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.989Rint = 0.062
14885 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.123All H-atom parameters refined
S = 1.00Δρmax = 0.22 e Å3
3601 reflectionsΔρmin = 0.28 e Å3
284 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.37858 (15)0.10863 (13)0.19150 (16)0.0341 (4)
C20.05239 (15)0.19513 (14)0.18187 (16)0.0341 (4)
C30.11890 (15)0.26681 (14)0.10184 (16)0.0345 (4)
C40.19407 (14)0.22888 (12)0.01473 (15)0.0290 (4)
C50.28973 (14)0.06881 (13)0.09354 (16)0.0296 (4)
C60.29987 (14)0.04135 (13)0.10744 (15)0.0293 (4)
C70.23139 (14)0.11227 (12)0.03302 (15)0.0292 (4)
C80.15392 (15)0.07277 (13)0.05515 (16)0.0303 (4)
C90.14378 (14)0.04151 (12)0.07069 (14)0.0272 (4)
C100.21080 (14)0.11406 (12)0.00472 (15)0.0274 (4)
C110.31771 (17)0.22020 (14)0.18754 (18)0.0385 (5)
C120.17909 (18)0.30711 (15)0.0320 (2)0.0398 (5)
C130.00241 (18)0.00971 (16)0.2378 (2)0.0392 (5)
C140.26336 (16)0.31053 (13)0.05997 (17)0.0360 (4)
C150.3930 (2)0.06468 (18)0.32525 (19)0.0451 (5)
C160.48967 (18)0.11344 (19)0.1319 (2)0.0467 (5)
C170.3878 (2)0.32150 (17)0.2094 (3)0.0542 (6)
F10.26308 (9)0.29590 (8)0.18444 (9)0.0456 (3)
F20.36909 (9)0.30578 (9)0.03196 (11)0.0535 (3)
F30.23105 (10)0.41370 (7)0.03869 (11)0.0567 (4)
H30.1077 (15)0.3436 (14)0.1152 (15)0.037 (5)*
H50.3379 (15)0.1191 (13)0.1455 (15)0.032 (4)*
H80.1097 (15)0.1192 (13)0.1019 (16)0.032 (5)*
H110.2583 (17)0.2200 (14)0.2547 (18)0.047 (5)*
H12A0.1440 (18)0.3053 (17)0.054 (2)0.059 (6)*
H13A0.0493 (18)0.0488 (17)0.2926 (19)0.056 (6)*
H15A0.4327 (18)0.1160 (16)0.381 (2)0.055 (6)*
H16A0.4774 (17)0.1451 (15)0.045 (2)0.052 (6)*
H17A0.431 (2)0.3160 (17)0.292 (2)0.067 (7)*
H12B0.123 (2)0.3111 (18)0.096 (2)0.079 (8)*
H13B0.0482 (19)0.0350 (17)0.186 (2)0.063 (7)*
H15B0.321 (2)0.0536 (17)0.3611 (19)0.064 (7)*
H16B0.5442 (18)0.1583 (16)0.1821 (18)0.056 (6)*
H17B0.341 (2)0.3878 (18)0.215 (2)0.070 (7)*
H12C0.2183 (18)0.3748 (18)0.0362 (19)0.057 (6)*
H13C0.043 (2)0.0356 (19)0.285 (2)0.073 (7)*
H15C0.4393 (19)0.0050 (19)0.3299 (19)0.065 (6)*
H16C0.5235 (18)0.0373 (18)0.1283 (19)0.058 (6)*
H17C0.438 (2)0.3315 (17)0.139 (2)0.065 (7)*
N10.06657 (11)0.08403 (10)0.15980 (12)0.0298 (3)
N20.25658 (12)0.21959 (10)0.06281 (13)0.0343 (4)
O20.01422 (11)0.22857 (10)0.26542 (12)0.0471 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0344 (11)0.0314 (9)0.0358 (10)0.0055 (8)0.0025 (8)0.0057 (7)
C20.0367 (11)0.0281 (9)0.0367 (9)0.0076 (7)0.0035 (8)0.0020 (7)
C30.0419 (12)0.0223 (9)0.0390 (10)0.0050 (8)0.0021 (8)0.0018 (7)
C40.0312 (10)0.0240 (8)0.0319 (9)0.0006 (7)0.0018 (8)0.0017 (7)
C50.0279 (10)0.0267 (9)0.0337 (9)0.0021 (7)0.0028 (8)0.0002 (7)
C60.0272 (10)0.0272 (9)0.0333 (9)0.0023 (7)0.0006 (7)0.0038 (7)
C70.0320 (10)0.0234 (8)0.0323 (9)0.0033 (7)0.0025 (8)0.0026 (7)
C80.0323 (10)0.0248 (8)0.0332 (9)0.0008 (7)0.0022 (8)0.0013 (7)
C90.0278 (10)0.0244 (9)0.0292 (8)0.0021 (7)0.0002 (7)0.0015 (7)
C100.0282 (9)0.0221 (8)0.0321 (9)0.0005 (7)0.0024 (7)0.0023 (7)
C110.0455 (12)0.0305 (10)0.0386 (10)0.0055 (8)0.0043 (9)0.0069 (8)
C120.0467 (13)0.0227 (10)0.0500 (13)0.0006 (8)0.0016 (11)0.0010 (8)
C130.0414 (12)0.0320 (10)0.0425 (11)0.0003 (9)0.0130 (10)0.0033 (9)
C140.0400 (12)0.0266 (10)0.0412 (10)0.0011 (8)0.0009 (8)0.0003 (8)
C150.0515 (14)0.0441 (12)0.0385 (11)0.0039 (11)0.0075 (10)0.0044 (9)
C160.0371 (12)0.0510 (13)0.0512 (13)0.0104 (10)0.0025 (10)0.0085 (11)
C170.0670 (17)0.0357 (12)0.0579 (15)0.0130 (11)0.0123 (13)0.0090 (10)
F10.0558 (8)0.0426 (6)0.0375 (6)0.0063 (5)0.0037 (5)0.0076 (5)
F20.0396 (7)0.0523 (7)0.0693 (8)0.0155 (5)0.0086 (6)0.0117 (6)
F30.0759 (9)0.0204 (5)0.0711 (8)0.0004 (5)0.0183 (6)0.0024 (5)
N10.0311 (8)0.0248 (7)0.0327 (8)0.0016 (6)0.0052 (6)0.0018 (6)
N20.0427 (10)0.0217 (7)0.0380 (8)0.0029 (6)0.0024 (7)0.0024 (6)
O20.0557 (9)0.0343 (7)0.0485 (8)0.0106 (6)0.0194 (7)0.0018 (6)
Geometric parameters (Å, º) top
C6—C71.412 (2)C11—C171.514 (3)
C7—C81.377 (2)C11—H111.05 (2)
C8—C91.411 (2)C12—N21.451 (2)
C9—C101.420 (2)C12—H12A0.98 (2)
C5—C101.419 (2)C12—H12B0.99 (3)
C5—C61.359 (2)C12—H12C0.95 (2)
C9—N11.395 (2)C13—N11.462 (2)
C2—N11.387 (2)C13—H13A0.92 (2)
C2—C31.437 (2)C13—H13B0.97 (2)
C3—C41.345 (2)C13—H13C0.95 (2)
C4—C101.432 (2)C14—F11.336 (2)
C2—O21.236 (2)C14—F31.3365 (19)
C7—N21.380 (2)C14—F21.341 (2)
C1—C61.514 (2)C15—H15A0.97 (2)
C1—C151.521 (3)C15—H15B0.98 (2)
C1—C161.530 (3)C15—H15C1.02 (2)
C1—C111.552 (2)C16—H16A1.00 (2)
C3—H30.957 (17)C16—H16B0.99 (2)
C4—C141.503 (2)C16—H16C1.02 (2)
C5—H50.994 (17)C17—H17A1.01 (2)
C8—H80.910 (18)C17—H17B0.99 (2)
C11—N21.482 (2)C17—H17C1.00 (2)
C6—C1—C15113.20 (15)H12A—C12—H12B111 (2)
C6—C1—C16108.74 (14)N2—C12—H12C108.2 (13)
C15—C1—C16110.19 (17)H12A—C12—H12C104.5 (17)
C6—C1—C11100.18 (14)H12B—C12—H12C106.8 (18)
C15—C1—C11111.36 (16)N1—C13—H13A110.5 (13)
C16—C1—C11112.86 (16)N1—C13—H13B110.9 (12)
O2—C2—N1120.99 (16)H13A—C13—H13B107.0 (18)
O2—C2—C3123.12 (15)N1—C13—H13C109.3 (14)
N1—C2—C3115.89 (15)H13A—C13—H13C109.0 (18)
C4—C3—C2122.27 (15)H13B—C13—H13C110.1 (19)
C4—C3—H3121.7 (11)F1—C14—F3106.01 (13)
C2—C3—H3116.0 (11)F1—C14—F2105.91 (15)
C3—C4—C10121.50 (15)F3—C14—F2106.29 (14)
C3—C4—C14118.20 (14)F1—C14—C4113.58 (14)
C10—C4—C14120.27 (14)F3—C14—C4112.75 (15)
C6—C5—C10120.80 (16)F2—C14—C4111.74 (14)
C6—C5—H5120.3 (9)C1—C15—H15A111.7 (12)
C10—C5—H5118.9 (9)C1—C15—H15B110.9 (12)
C5—C6—C7120.01 (15)H15A—C15—H15B105.8 (17)
C5—C6—C1130.74 (15)C1—C15—H15C111.9 (12)
C7—C6—C1109.22 (13)H15A—C15—H15C104.8 (17)
C8—C7—N2128.57 (15)H15B—C15—H15C111.5 (17)
C8—C7—C6121.60 (14)C1—C16—H16A108.0 (12)
N2—C7—C6109.83 (14)C1—C16—H16B112.3 (12)
C7—C8—C9118.58 (16)H16A—C16—H16B109.8 (16)
C7—C8—H8120.8 (11)C1—C16—H16C110.5 (12)
C9—C8—H8120.6 (11)H16A—C16—H16C110.8 (16)
N1—C9—C8119.94 (14)H16B—C16—H16C105.4 (17)
N1—C9—C10119.49 (13)C11—C17—H17A110.1 (12)
C8—C9—C10120.57 (15)C11—C17—H17B111.1 (14)
C5—C10—C9118.43 (14)H17A—C17—H17B105.8 (18)
C5—C10—C4124.28 (15)C11—C17—H17C110.2 (13)
C9—C10—C4117.29 (14)H17A—C17—H17C110.8 (19)
N2—C11—C17112.94 (16)H17B—C17—H17C108.7 (17)
N2—C11—C1103.51 (13)C2—N1—C9123.48 (14)
C17—C11—C1116.77 (18)C2—N1—C13116.81 (14)
N2—C11—H11106.2 (10)C9—N1—C13119.69 (13)
C17—C11—H11107.7 (10)C7—N2—C12121.09 (15)
C1—C11—H11109.2 (10)C7—N2—C11107.65 (13)
N2—C12—H12A115.7 (13)C12—N2—C11118.90 (14)
N2—C12—H12B110.4 (14)
C6—C7—N2—C1118.60 (19)C14—C4—C10—C50.9 (2)
C8—C7—N2—C1220.5 (3)C3—C4—C10—C90.8 (2)
O2—C2—C3—C4177.31 (18)C14—C4—C10—C9178.89 (15)
N1—C2—C3—C43.0 (3)C6—C1—C11—N228.76 (17)
C2—C3—C4—C101.1 (3)C15—C1—C11—N2148.76 (16)
C2—C3—C4—C14177.06 (16)C16—C1—C11—N286.70 (18)
C10—C5—C6—C70.0 (2)C6—C1—C11—C17153.51 (17)
C10—C5—C6—C1178.02 (16)C15—C1—C11—C1786.5 (2)
C15—C1—C6—C544.0 (3)C16—C1—C11—C1738.1 (2)
C16—C1—C6—C578.8 (2)C3—C4—C14—F1127.99 (17)
C11—C1—C6—C5162.70 (18)C10—C4—C14—F153.8 (2)
C15—C1—C6—C7137.77 (17)C3—C4—C14—F37.4 (2)
C16—C1—C6—C799.41 (17)C10—C4—C14—F3174.45 (15)
C11—C1—C6—C719.12 (17)C3—C4—C14—F2112.27 (18)
C5—C6—C7—C80.4 (2)C10—C4—C14—F265.9 (2)
C1—C6—C7—C8177.98 (15)O2—C2—N1—C9177.10 (16)
C5—C6—C7—N2179.73 (14)C3—C2—N1—C93.2 (2)
C1—C6—C7—N21.32 (18)O2—C2—N1—C131.3 (2)
N2—C7—C8—C9179.02 (16)C3—C2—N1—C13178.38 (16)
C6—C7—C8—C90.1 (2)C8—C9—N1—C2179.20 (15)
C7—C8—C9—N1179.58 (15)C10—C9—N1—C21.5 (2)
C7—C8—C9—C101.1 (2)C8—C9—N1—C130.8 (2)
C6—C5—C10—C90.9 (2)C10—C9—N1—C13179.86 (16)
C6—C5—C10—C4179.28 (16)C6—C7—N2—C12160.24 (16)
N1—C9—C10—C5179.18 (14)C8—C7—N2—C11162.17 (17)
C8—C9—C10—C51.5 (2)C17—C11—N2—C7157.40 (18)
N1—C9—C10—C40.6 (2)C1—C11—N2—C730.20 (18)
C8—C9—C10—C4178.70 (15)C17—C11—N2—C1260.0 (3)
C3—C4—C10—C5179.00 (16)C1—C11—N2—C12172.83 (16)

Experimental details

(ld425)(ld489)(ld473)
Crystal data
Chemical formulaC13H14N2O3C15H15F3N2O2C17H19F3N2O
Mr246.26312.29324.34
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)180180180
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)
V3)2342 (3)1423.44 (14)1581.43 (9)
Z844
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.100.120.11
Crystal size (mm)0.56 × 0.28 × 0.110.42 × 0.22 × 0.140.32 × 0.16 × 0.12
Data collection
DiffractometerRigaku CrystalClear-SM Expert 2.0 r4
diffractometer
KappaCCD
diffractometer
KappaCCD
diffractometer
Absorption correctionMulti-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, Tmax0.973, 1.0280.958, 0.9980.943, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
14043, 5763, 4634 7357, 3199, 2235 14885, 3601, 2179
Rint0.0770.0320.062
(sin θ/λ)max1)0.6670.6470.649
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 reflections576331993601
No. of parameters437259284
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.31, 0.490.31, 0.250.22, 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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