With the aim of improving the solubility of ciprofloxacin, polybasic organic acids were utilized to react with ciprofloxacin in different stoichiometric proportions. The use of the solvent drop grinding (SDG) method, as well as the solvent evaporation method, resulted in the crystalline salts ciprofloxacin/fumaric acid (1:1, 2:1), ciprofloxacin/maleic acid (1:1) and ciprofloxacin/citric acid (2:1). The solubilities of these salts in pure water (pH 7.0) were determined using high-performance liquid chromatography (HPLC) at 310 K, with the salts showing considerably greater solubility than ciprofloxacin itself and, interestingly, ciprofloxacin/fumaric acid (2:1) being more soluble than ciprofloxacin/fumaric acid (1:1). Intrigued by this phenomenon, we undertook a comparison of the crystal structures of the salts: the three-dimensional sandwich-like structure observed in the 2:1 salt indicates that the preferred stacking may be a factor in increasing the solubility of ciprofloxacin.
Supporting information
CCDC references: 1060662; 1060663; 1060664; 1060665
For all compounds, data collection: CrystalClear (Rigaku Inc., 2008); cell refinement: CrystalClear (Rigaku Inc., 2008); data reduction: CrystalClear (Rigaku Inc., 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII(Johnson,1976)andPLUTON(Spek,1990); software used to prepare material for publication: SHELXL97(Sheldrick, 1997).
Crystal data top
C17H19FN3O3·C4H3O4·H2O | Z = 2 |
Mr = 465.43 | F(000) = 488 |
Triclinic, P1 | Dx = 1.474 Mg m−3 |
a = 9.579 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 9.806 (2) Å | Cell parameters from 3412 reflections |
c = 11.612 (4) Å | θ = 3.9–70.0° |
α = 78.66 (2)° | µ = 1.02 mm−1 |
β = 89.44 (3)° | T = 293 K |
γ = 78.85 (4)° | Prism, colorless |
V = 1048.8 (5) Å3 | 0.72 × 0.23 × 0.19 mm |
Data collection top
CCD diffractometer | 3866 independent reflections |
Radiation source: fine-focus sealed tube | 3412 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.055 |
Detector resolution: 0 pixels mm-1 | θmax = 70.0°, θmin = 3.9° |
ωκ scans | h = −11→11 |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | k = −11→6 |
Tmin = 0.721, Tmax = 1.000 | l = −14→13 |
15473 measured reflections | |
Refinement top
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0826P)2 + 0.0488P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3866 reflections | Δρmax = 0.30 e Å−3 |
323 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0103 (11) |
Crystal data top
C17H19FN3O3·C4H3O4·H2O | γ = 78.85 (4)° |
Mr = 465.43 | V = 1048.8 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.579 (3) Å | Cu Kα radiation |
b = 9.806 (2) Å | µ = 1.02 mm−1 |
c = 11.612 (4) Å | T = 293 K |
α = 78.66 (2)° | 0.72 × 0.23 × 0.19 mm |
β = 89.44 (3)° | |
Data collection top
CCD diffractometer | 3866 independent reflections |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | 3412 reflections with I > 2σ(I) |
Tmin = 0.721, Tmax = 1.000 | Rint = 0.055 |
15473 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.30 e Å−3 |
3866 reflections | Δρmin = −0.22 e Å−3 |
323 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.19992 (14) | 0.47332 (13) | 0.37331 (10) | 0.0328 (3) | |
H1A | 0.2673 | 0.5284 | 0.3476 | 0.039* | |
C2 | 0.06799 (14) | 0.51155 (13) | 0.31929 (10) | 0.0335 (3) | |
C3 | −0.03972 (14) | 0.43085 (13) | 0.35557 (10) | 0.0334 (3) | |
C4 | 0.00154 (13) | 0.30974 (13) | 0.45142 (10) | 0.0310 (3) | |
C5 | −0.09558 (13) | 0.22261 (14) | 0.49555 (11) | 0.0339 (3) | |
H5A | −0.1866 | 0.2410 | 0.4618 | 0.041* | |
C6 | −0.05703 (13) | 0.11194 (14) | 0.58705 (11) | 0.0335 (3) | |
C7 | 0.07918 (13) | 0.07750 (13) | 0.64303 (10) | 0.0312 (3) | |
C8 | 0.17488 (13) | 0.16333 (13) | 0.59937 (10) | 0.0321 (3) | |
H8A | 0.2653 | 0.1450 | 0.6343 | 0.038* | |
C9 | 0.13834 (13) | 0.27704 (13) | 0.50387 (10) | 0.0300 (3) | |
C10 | 0.37955 (13) | 0.32797 (14) | 0.51529 (11) | 0.0352 (3) | |
H10A | 0.3867 | 0.3515 | 0.5930 | 0.042* | |
C11 | 0.47966 (15) | 0.19843 (16) | 0.49497 (13) | 0.0450 (3) | |
H11A | 0.4464 | 0.1419 | 0.4452 | 0.054* | |
H11B | 0.5437 | 0.1448 | 0.5593 | 0.054* | |
C12 | 0.50337 (15) | 0.34261 (17) | 0.43852 (15) | 0.0496 (4) | |
H12A | 0.5819 | 0.3760 | 0.4687 | 0.060* | |
H12B | 0.4846 | 0.3732 | 0.3545 | 0.060* | |
C13 | 0.04353 (15) | 0.63762 (14) | 0.22173 (11) | 0.0394 (3) | |
C14 | 0.02861 (14) | −0.05593 (14) | 0.83636 (11) | 0.0383 (3) | |
H14A | −0.0711 | −0.0231 | 0.8131 | 0.046* | |
H14B | 0.0533 | 0.0025 | 0.8884 | 0.046* | |
C15 | 0.05304 (14) | −0.20951 (14) | 0.89997 (11) | 0.0393 (3) | |
H15A | −0.0040 | −0.2178 | 0.9696 | 0.047* | |
H15B | 0.0238 | −0.2671 | 0.8491 | 0.047* | |
C16 | 0.29691 (14) | −0.24126 (14) | 0.82946 (12) | 0.0378 (3) | |
H16A | 0.2782 | −0.3016 | 0.7768 | 0.045* | |
H16B | 0.3964 | −0.2694 | 0.8544 | 0.045* | |
C17 | 0.26797 (13) | −0.08836 (14) | 0.76453 (12) | 0.0364 (3) | |
H17A | 0.2949 | −0.0285 | 0.8144 | 0.044* | |
H17B | 0.3244 | −0.0791 | 0.6946 | 0.044* | |
C18 | 0.31651 (14) | 0.36607 (14) | 0.06978 (12) | 0.0380 (3) | |
C19 | 0.31904 (14) | 0.21543 (14) | 0.05956 (12) | 0.0388 (3) | |
H19A | 0.2882 | 0.1992 | −0.0113 | 0.047* | |
C20 | 0.36202 (14) | 0.10492 (14) | 0.14431 (11) | 0.0370 (3) | |
H20A | 0.3878 | 0.1190 | 0.2174 | 0.044* | |
C21 | 0.37023 (14) | −0.04141 (14) | 0.12584 (11) | 0.0371 (3) | |
N1 | 0.23751 (11) | 0.36073 (11) | 0.46133 (9) | 0.0316 (3) | |
N2 | 0.11676 (11) | −0.04273 (11) | 0.73146 (9) | 0.0329 (3) | |
N3 | 0.20627 (12) | −0.26150 (12) | 0.93425 (9) | 0.0353 (3) | |
H3A | 0.2284 (18) | −0.2121 (19) | 0.9904 (16) | 0.047 (4)* | |
H3B | 0.229 (2) | −0.364 (2) | 0.9670 (18) | 0.062 (5)* | |
O1 | 0.13170 (12) | 0.70939 (11) | 0.19047 (9) | 0.0500 (3) | |
O2 | −0.08356 (13) | 0.66818 (13) | 0.16873 (10) | 0.0558 (3) | |
H2A | −0.133 (3) | 0.605 (3) | 0.205 (2) | 0.080 (7)* | |
O3 | −0.16330 (11) | 0.46215 (11) | 0.30945 (9) | 0.0462 (3) | |
O4 | 0.28813 (14) | 0.45614 (11) | −0.02439 (10) | 0.0589 (3) | |
O5 | 0.34710 (13) | 0.39136 (11) | 0.16600 (10) | 0.0535 (3) | |
O6 | 0.31810 (14) | −0.06803 (11) | 0.04040 (10) | 0.0569 (3) | |
O7 | 0.44040 (14) | −0.13874 (12) | 0.21017 (10) | 0.0558 (3) | |
H7A | 0.449 (3) | −0.235 (3) | 0.197 (2) | 0.085 (7)* | |
O8 | 0.48705 (17) | −0.39452 (13) | 0.17796 (13) | 0.0669 (4) | |
H8B | 0.429 (3) | −0.455 (3) | 0.165 (2) | 0.085 (7)* | |
H8C | 0.565 (3) | −0.414 (3) | 0.135 (2) | 0.086 (7)* | |
F1 | −0.15187 (8) | 0.02741 (9) | 0.62348 (7) | 0.0470 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0373 (7) | 0.0317 (6) | 0.0267 (6) | −0.0054 (5) | 0.0024 (5) | −0.0007 (4) |
C2 | 0.0382 (7) | 0.0335 (7) | 0.0247 (6) | −0.0018 (5) | −0.0007 (5) | −0.0005 (5) |
C3 | 0.0354 (6) | 0.0359 (7) | 0.0257 (6) | −0.0015 (5) | −0.0046 (5) | −0.0039 (5) |
C4 | 0.0320 (6) | 0.0337 (7) | 0.0244 (6) | −0.0024 (5) | −0.0021 (5) | −0.0024 (5) |
C5 | 0.0288 (6) | 0.0397 (7) | 0.0303 (6) | −0.0040 (5) | −0.0043 (5) | −0.0023 (5) |
C6 | 0.0295 (6) | 0.0384 (7) | 0.0313 (6) | −0.0087 (5) | 0.0012 (5) | −0.0015 (5) |
C7 | 0.0317 (6) | 0.0332 (6) | 0.0251 (6) | −0.0029 (5) | −0.0002 (5) | −0.0006 (4) |
C8 | 0.0291 (6) | 0.0375 (7) | 0.0263 (6) | −0.0049 (5) | −0.0026 (4) | 0.0002 (5) |
C9 | 0.0302 (6) | 0.0335 (6) | 0.0245 (6) | −0.0048 (5) | 0.0002 (4) | −0.0027 (4) |
C10 | 0.0315 (6) | 0.0390 (7) | 0.0327 (6) | −0.0079 (5) | −0.0041 (5) | −0.0001 (5) |
C11 | 0.0370 (7) | 0.0439 (8) | 0.0474 (8) | −0.0009 (6) | −0.0037 (6) | 0.0007 (6) |
C12 | 0.0320 (7) | 0.0539 (9) | 0.0549 (9) | −0.0071 (6) | 0.0037 (6) | 0.0072 (6) |
C13 | 0.0482 (8) | 0.0367 (7) | 0.0280 (6) | −0.0021 (6) | −0.0017 (5) | 0.0002 (5) |
C14 | 0.0376 (7) | 0.0413 (7) | 0.0288 (6) | −0.0013 (5) | 0.0051 (5) | 0.0038 (5) |
C15 | 0.0387 (7) | 0.0429 (8) | 0.0317 (6) | −0.0088 (5) | 0.0021 (5) | 0.0044 (5) |
C16 | 0.0336 (6) | 0.0370 (7) | 0.0372 (7) | −0.0024 (5) | −0.0029 (5) | 0.0022 (5) |
C17 | 0.0293 (6) | 0.0385 (7) | 0.0357 (6) | −0.0054 (5) | −0.0022 (5) | 0.0055 (5) |
C18 | 0.0338 (6) | 0.0325 (7) | 0.0453 (7) | −0.0040 (5) | 0.0024 (5) | −0.0046 (5) |
C19 | 0.0403 (7) | 0.0352 (7) | 0.0392 (7) | −0.0076 (5) | −0.0062 (5) | −0.0027 (5) |
C20 | 0.0394 (7) | 0.0365 (7) | 0.0342 (6) | −0.0070 (5) | −0.0050 (5) | −0.0048 (5) |
C21 | 0.0424 (7) | 0.0345 (7) | 0.0328 (6) | −0.0092 (5) | −0.0028 (5) | −0.0010 (5) |
N1 | 0.0300 (5) | 0.0346 (6) | 0.0270 (5) | −0.0057 (4) | −0.0015 (4) | 0.0013 (4) |
N2 | 0.0289 (5) | 0.0371 (6) | 0.0269 (5) | −0.0034 (4) | 0.0007 (4) | 0.0045 (4) |
N3 | 0.0437 (6) | 0.0311 (6) | 0.0281 (5) | −0.0067 (4) | −0.0052 (4) | 0.0016 (4) |
O1 | 0.0570 (6) | 0.0431 (6) | 0.0428 (6) | −0.0109 (5) | 0.0008 (5) | 0.0096 (4) |
O2 | 0.0585 (7) | 0.0526 (7) | 0.0455 (6) | −0.0107 (5) | −0.0183 (5) | 0.0170 (5) |
O3 | 0.0399 (5) | 0.0483 (6) | 0.0428 (5) | −0.0056 (4) | −0.0154 (4) | 0.0071 (4) |
O4 | 0.0821 (8) | 0.0336 (6) | 0.0541 (6) | −0.0061 (5) | −0.0073 (6) | 0.0035 (4) |
O5 | 0.0688 (7) | 0.0417 (6) | 0.0505 (6) | −0.0076 (5) | 0.0001 (5) | −0.0132 (4) |
O6 | 0.0856 (9) | 0.0418 (6) | 0.0450 (6) | −0.0200 (5) | −0.0212 (5) | −0.0037 (4) |
O7 | 0.0826 (8) | 0.0339 (6) | 0.0447 (6) | −0.0016 (5) | −0.0205 (5) | −0.0015 (4) |
O8 | 0.0744 (9) | 0.0398 (6) | 0.0884 (9) | −0.0129 (6) | 0.0200 (7) | −0.0162 (6) |
F1 | 0.0363 (4) | 0.0540 (5) | 0.0467 (5) | −0.0180 (3) | −0.0027 (3) | 0.0086 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.3428 (16) | C14—N2 | 1.4743 (15) |
C1—C2 | 1.3678 (19) | C14—C15 | 1.5158 (18) |
C1—H1A | 0.9300 | C14—H14A | 0.9700 |
C2—C3 | 1.430 (2) | C14—H14B | 0.9700 |
C2—C13 | 1.4862 (17) | C15—N3 | 1.4882 (18) |
C3—O3 | 1.2609 (17) | C15—H15A | 0.9700 |
C3—C4 | 1.4535 (17) | C15—H15B | 0.9700 |
C4—C9 | 1.4025 (18) | C16—N3 | 1.4917 (17) |
C4—C5 | 1.4085 (19) | C16—C17 | 1.5140 (18) |
C5—C6 | 1.3573 (18) | C16—H16A | 0.9700 |
C5—H5A | 0.9300 | C16—H16B | 0.9700 |
C6—F1 | 1.3554 (15) | C17—N2 | 1.4623 (16) |
C6—C7 | 1.4138 (19) | C17—H17A | 0.9700 |
C7—C8 | 1.3883 (18) | C17—H17B | 0.9700 |
C7—N2 | 1.3932 (16) | C18—O5 | 1.2406 (18) |
C8—C9 | 1.4021 (17) | C18—O4 | 1.2581 (18) |
C8—H8A | 0.9300 | C18—C19 | 1.5006 (19) |
C9—N1 | 1.3974 (17) | C19—C20 | 1.315 (2) |
C10—N1 | 1.4545 (17) | C19—H19A | 0.9300 |
C10—C12 | 1.4890 (19) | C20—C21 | 1.4793 (19) |
C10—C11 | 1.494 (2) | C20—H20A | 0.9300 |
C10—H10A | 0.9800 | C21—O6 | 1.2099 (18) |
C11—C12 | 1.496 (2) | C21—O7 | 1.3109 (17) |
C11—H11A | 0.9700 | N3—H3A | 0.933 (19) |
C11—H11B | 0.9700 | N3—H3B | 0.99 (2) |
C12—H12A | 0.9700 | O2—H2A | 0.89 (2) |
C12—H12B | 0.9700 | O7—H7A | 0.97 (3) |
C13—O1 | 1.2099 (19) | O8—H8B | 0.92 (3) |
C13—O2 | 1.3235 (19) | O8—H8C | 0.91 (3) |
| | | |
N1—C1—C2 | 123.64 (12) | C15—C14—H14A | 109.7 |
N1—C1—H1A | 118.2 | N2—C14—H14B | 109.7 |
C2—C1—H1A | 118.2 | C15—C14—H14B | 109.7 |
C1—C2—C3 | 120.45 (11) | H14A—C14—H14B | 108.2 |
C1—C2—C13 | 117.24 (12) | N3—C15—C14 | 110.08 (12) |
C3—C2—C13 | 122.30 (12) | N3—C15—H15A | 109.6 |
O3—C3—C2 | 123.01 (12) | C14—C15—H15A | 109.6 |
O3—C3—C4 | 121.44 (12) | N3—C15—H15B | 109.6 |
C2—C3—C4 | 115.55 (11) | C14—C15—H15B | 109.6 |
C9—C4—C5 | 117.93 (11) | H15A—C15—H15B | 108.2 |
C9—C4—C3 | 121.18 (12) | N3—C16—C17 | 111.41 (11) |
C5—C4—C3 | 120.88 (12) | N3—C16—H16A | 109.3 |
C6—C5—C4 | 120.37 (12) | C17—C16—H16A | 109.3 |
C6—C5—H5A | 119.8 | N3—C16—H16B | 109.3 |
C4—C5—H5A | 119.8 | C17—C16—H16B | 109.3 |
F1—C6—C5 | 118.35 (11) | H16A—C16—H16B | 108.0 |
F1—C6—C7 | 118.51 (11) | N2—C17—C16 | 109.81 (11) |
C5—C6—C7 | 123.09 (12) | N2—C17—H17A | 109.7 |
C8—C7—N2 | 122.47 (11) | C16—C17—H17A | 109.7 |
C8—C7—C6 | 116.49 (11) | N2—C17—H17B | 109.7 |
N2—C7—C6 | 120.88 (12) | C16—C17—H17B | 109.7 |
C7—C8—C9 | 121.52 (12) | H17A—C17—H17B | 108.2 |
C7—C8—H8A | 119.2 | O5—C18—O4 | 125.70 (13) |
C9—C8—H8A | 119.2 | O5—C18—C19 | 119.07 (12) |
N1—C9—C8 | 120.14 (11) | O4—C18—C19 | 115.16 (13) |
N1—C9—C4 | 119.28 (11) | C20—C19—C18 | 124.26 (13) |
C8—C9—C4 | 120.57 (12) | C20—C19—H19A | 117.9 |
N1—C10—C12 | 118.78 (11) | C18—C19—H19A | 117.9 |
N1—C10—C11 | 118.37 (12) | C19—C20—C21 | 121.41 (12) |
C12—C10—C11 | 60.19 (10) | C19—C20—H20A | 119.3 |
N1—C10—H10A | 116.0 | C21—C20—H20A | 119.3 |
C12—C10—H10A | 116.0 | O6—C21—O7 | 123.49 (13) |
C11—C10—H10A | 116.0 | O6—C21—C20 | 122.97 (12) |
C10—C11—C12 | 59.75 (10) | O7—C21—C20 | 113.54 (12) |
C10—C11—H11A | 117.8 | C1—N1—C9 | 119.88 (11) |
C12—C11—H11A | 117.8 | C1—N1—C10 | 120.37 (11) |
C10—C11—H11B | 117.8 | C9—N1—C10 | 119.72 (10) |
C12—C11—H11B | 117.8 | C7—N2—C17 | 116.80 (10) |
H11A—C11—H11B | 114.9 | C7—N2—C14 | 118.19 (10) |
C10—C12—C11 | 60.06 (10) | C17—N2—C14 | 110.74 (10) |
C10—C12—H12A | 117.8 | C15—N3—C16 | 110.65 (10) |
C11—C12—H12A | 117.8 | C15—N3—H3A | 107.7 (11) |
C10—C12—H12B | 117.8 | C16—N3—H3A | 111.5 (11) |
C11—C12—H12B | 117.8 | C15—N3—H3B | 112.7 (12) |
H12A—C12—H12B | 114.9 | C16—N3—H3B | 104.9 (11) |
O1—C13—O2 | 120.72 (12) | H3A—N3—H3B | 109.4 (16) |
O1—C13—C2 | 123.78 (13) | C13—O2—H2A | 107.4 (16) |
O2—C13—C2 | 115.50 (13) | C21—O7—H7A | 113.6 (15) |
N2—C14—C15 | 109.73 (11) | H8B—O8—H8C | 106 (2) |
N2—C14—H14A | 109.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O6i | 0.933 (19) | 1.968 (19) | 2.8280 (18) | 152.3 (15) |
N3—H3A···O1ii | 0.933 (19) | 2.526 (18) | 3.0244 (18) | 113.7 (13) |
N3—H3B···O4ii | 0.99 (2) | 1.73 (2) | 2.6752 (17) | 160.2 (18) |
O2—H2A···O3 | 0.89 (2) | 1.73 (3) | 2.5708 (17) | 156 (2) |
O7—H7A···O8 | 0.97 (3) | 1.60 (3) | 2.5618 (17) | 172 (2) |
O8—H8B···O5iii | 0.92 (3) | 1.83 (3) | 2.726 (2) | 165 (2) |
O8—H8C···O4iv | 0.91 (3) | 1.93 (3) | 2.833 (2) | 171 (2) |
Symmetry codes: (i) x, y, z+1; (ii) x, y−1, z+1; (iii) x, y−1, z; (iv) −x+1, −y, −z. |
Crystal data top
2(C17H19FN3O3)·C4H2O4·3(H2O) | Z = 4 |
Mr = 832.81 | F(000) = 1752 |
Monoclinic, P21/n | Dx = 1.450 Mg m−3 |
a = 9.922 (4) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 30.199 (9) Å | µ = 0.99 mm−1 |
c = 13.528 (8) Å | T = 293 K |
β = 109.717 (13)° | Prism, colorless |
V = 3816 (3) Å3 | 0.43 × 0.12 × 0.03 mm |
Data collection top
CCD diffractometer | 7316 independent reflections |
Radiation source: fine-focus sealed tube | 5695 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.125 |
Detector resolution: 0 pixels mm-1 | θmax = 72.4°, θmin = 3.8° |
ωκ scans | h = −11→12 |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | k = −37→36 |
Tmin = 0.676, Tmax = 0.971 | l = −13→15 |
36407 measured reflections | |
Refinement top
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)] = 0.082 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.249 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1422P)2 + 0.8915P] where P = (Fo2 + 2Fc2)/3 |
7316 reflections | (Δ/σ)max < 0.001 |
588 parameters | Δρmax = 0.41 e Å−3 |
14 restraints | Δρmin = −0.56 e Å−3 |
Crystal data top
2(C17H19FN3O3)·C4H2O4·3(H2O) | V = 3816 (3) Å3 |
Mr = 832.81 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 9.922 (4) Å | µ = 0.99 mm−1 |
b = 30.199 (9) Å | T = 293 K |
c = 13.528 (8) Å | 0.43 × 0.12 × 0.03 mm |
β = 109.717 (13)° | |
Data collection top
CCD diffractometer | 7316 independent reflections |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | 5695 reflections with I > 2σ(I) |
Tmin = 0.676, Tmax = 0.971 | Rint = 0.125 |
36407 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.082 | 14 restraints |
wR(F2) = 0.249 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.41 e Å−3 |
7316 reflections | Δρmin = −0.56 e Å−3 |
588 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
F1A | 0.06277 (18) | 0.03015 (7) | 0.76900 (19) | 0.0692 (6) | |
F1B | 0.93352 (17) | −0.06347 (6) | 0.73563 (16) | 0.0582 (5) | |
N1A | 0.6455 (2) | 0.05550 (7) | 0.91567 (17) | 0.0364 (5) | |
N1B | 0.3545 (2) | −0.02830 (7) | 0.58599 (17) | 0.0376 (5) | |
N2A | 0.1665 (2) | 0.11701 (8) | 0.80425 (19) | 0.0449 (6) | |
N2B | 0.7454 (3) | −0.13390 (8) | 0.6904 (2) | 0.0515 (6) | |
N3A | −0.0309 (2) | 0.18566 (8) | 0.80108 (19) | 0.0421 (5) | |
H3A | −0.019 (4) | 0.2019 (12) | 0.751 (2) | 0.066 (11)* | |
H3B | −0.094 (3) | 0.1965 (12) | 0.827 (3) | 0.059 (10)* | |
N3B | 0.8751 (3) | −0.21502 (9) | 0.7765 (2) | 0.0481 (6) | |
H3C | 0.935 (3) | −0.2291 (11) | 0.830 (2) | 0.058 (10)* | |
H3D | 0.854 (4) | −0.2346 (11) | 0.725 (2) | 0.072 (12)* | |
O1A | 0.9192 (3) | −0.05331 (10) | 0.9912 (3) | 0.0820 (9) | |
O1B | 0.2081 (2) | 0.10119 (7) | 0.56285 (19) | 0.0550 (6) | |
O2A | 0.7381 (3) | −0.09969 (8) | 0.9308 (2) | 0.0629 (6) | |
H2A | 0.641 (5) | −0.0973 (16) | 0.895 (4) | 0.084 (14)* | |
O2B | 0.4272 (3) | 0.12816 (7) | 0.6044 (2) | 0.0584 (6) | |
H2B | 0.513 (7) | 0.1198 (19) | 0.626 (5) | 0.112 (19)* | |
O3A | 0.4852 (2) | −0.07065 (6) | 0.86188 (17) | 0.0500 (5) | |
O3B | 0.6403 (2) | 0.07508 (7) | 0.66058 (18) | 0.0496 (5) | |
O4 | 0.3596 (3) | 0.27285 (14) | 1.0048 (2) | 0.0968 (11) | |
O5 | 0.5356 (2) | 0.26466 (9) | 1.15531 (17) | 0.0589 (6) | |
O6 | 0.9484 (2) | 0.23494 (9) | 1.02436 (17) | 0.0571 (6) | |
O7 | 0.7613 (2) | 0.22358 (7) | 0.88089 (15) | 0.0455 (5) | |
O8A | 0.1701 (4) | 0.30257 (19) | 1.0970 (5) | 0.079 (2) | 0.823 (18) |
H8A | 0.208 (7) | 0.2988 (19) | 1.046 (4) | 0.17 (3)* | |
H8B | 0.087 (3) | 0.2991 (14) | 1.046 (3) | 0.086 (14)* | |
O8B | 0.148 (2) | 0.3217 (8) | 1.0450 (19) | 0.069 (7)* | 0.177 (18) |
O9 | 0.4790 (5) | 0.19571 (17) | 0.7609 (4) | 0.1203 (14) | |
H9A | 0.428 (7) | 0.1769 (19) | 0.705 (4) | 0.144* | |
H9B | 0.579 (3) | 0.198 (2) | 0.801 (5) | 0.144* | |
O10A | 1.304 (3) | −0.1979 (4) | 0.7053 (7) | 0.126 (5) | 0.64 (5) |
H10C | 1.254 (14) | −0.207 (6) | 0.640 (3) | 0.44 (12)* | |
H10D | 1.327 (6) | −0.2268 (13) | 0.718 (14) | 0.33 (9)* | |
O10B | 1.249 (3) | −0.2095 (9) | 0.7047 (12) | 0.096 (6)* | 0.36 (5) |
C1A | 0.7325 (3) | 0.02005 (9) | 0.9353 (2) | 0.0408 (6) | |
H1AA | 0.8308 | 0.0250 | 0.9599 | 0.049* | |
C1B | 0.3109 (3) | 0.01383 (9) | 0.5766 (2) | 0.0395 (6) | |
H1BA | 0.2129 | 0.0191 | 0.5510 | 0.047* | |
C2A | 0.6853 (3) | −0.02282 (9) | 0.9212 (2) | 0.0397 (6) | |
C2B | 0.4005 (3) | 0.04985 (9) | 0.6019 (2) | 0.0371 (6) | |
C3A | 0.5342 (3) | −0.03169 (9) | 0.87993 (19) | 0.0373 (6) | |
C3B | 0.5521 (3) | 0.04306 (9) | 0.63788 (19) | 0.0367 (6) | |
C4A | 0.4423 (3) | 0.00647 (9) | 0.85890 (19) | 0.0355 (5) | |
C4B | 0.5996 (3) | −0.00223 (9) | 0.64732 (19) | 0.0345 (5) | |
C5A | 0.2922 (3) | 0.00134 (9) | 0.8201 (2) | 0.0399 (6) | |
H5AA | 0.2522 | −0.0268 | 0.8075 | 0.048* | |
C5B | 0.7467 (3) | −0.01228 (9) | 0.6834 (2) | 0.0389 (6) | |
H5BA | 0.8139 | 0.0105 | 0.7002 | 0.047* | |
C6A | 0.2066 (3) | 0.03727 (10) | 0.8012 (2) | 0.0414 (6) | |
C6B | 0.7904 (3) | −0.05487 (10) | 0.6937 (2) | 0.0400 (6) | |
C7A | 0.2572 (3) | 0.08122 (9) | 0.8169 (2) | 0.0369 (6) | |
C7B | 0.6959 (3) | −0.09141 (9) | 0.6695 (2) | 0.0388 (6) | |
C8A | 0.4060 (3) | 0.08614 (9) | 0.8537 (2) | 0.0362 (5) | |
H8AA | 0.4453 | 0.1144 | 0.8634 | 0.043* | |
C8B | 0.5492 (3) | −0.08135 (9) | 0.6317 (2) | 0.0406 (6) | |
H8BA | 0.4827 | −0.1042 | 0.6126 | 0.049* | |
C9A | 0.4968 (3) | 0.04942 (8) | 0.87611 (19) | 0.0333 (5) | |
C9B | 0.5019 (3) | −0.03771 (9) | 0.62223 (19) | 0.0351 (5) | |
C10A | 0.7035 (3) | 0.10004 (9) | 0.9300 (2) | 0.0432 (6) | |
H10A | 0.6934 | 0.1162 | 0.8651 | 0.052* | |
C10B | 0.2502 (3) | −0.06376 (11) | 0.5482 (3) | 0.0501 (7) | |
H10B | 0.2445 | −0.0764 | 0.4801 | 0.060* | |
C11A | 0.6918 (3) | 0.12754 (10) | 1.0181 (3) | 0.0533 (8) | |
H11A | 0.6726 | 0.1589 | 1.0054 | 0.064* | |
H11B | 0.6490 | 0.1141 | 1.0656 | 0.064* | |
C11B | 0.2245 (4) | −0.09553 (13) | 0.6235 (3) | 0.0630 (9) | |
H11C | 0.2766 | −0.0912 | 0.6976 | 0.076* | |
H11D | 0.2064 | −0.1262 | 0.6018 | 0.076* | |
C12A | 0.8332 (3) | 0.11065 (11) | 1.0201 (3) | 0.0536 (7) | |
H12C | 0.9002 | 0.1318 | 1.0088 | 0.064* | |
H12D | 0.8767 | 0.0870 | 1.0690 | 0.064* | |
C12B | 0.1133 (3) | −0.06182 (12) | 0.5683 (3) | 0.0592 (8) | |
H12A | 0.0280 | −0.0722 | 0.5135 | 0.071* | |
H12B | 0.0981 | −0.0372 | 0.6093 | 0.071* | |
C13A | 0.7912 (4) | −0.05929 (11) | 0.9503 (3) | 0.0527 (7) | |
C13B | 0.3362 (3) | 0.09469 (10) | 0.5879 (2) | 0.0421 (6) | |
C14A | 0.0305 (3) | 0.12070 (11) | 0.7179 (2) | 0.0457 (7) | |
H14A | −0.0012 | 0.0916 | 0.6894 | 0.055* | |
H14B | 0.0429 | 0.1388 | 0.6624 | 0.055* | |
C14B | 0.8649 (3) | −0.15152 (10) | 0.6607 (3) | 0.0494 (7) | |
H14C | 0.9196 | −0.1272 | 0.6464 | 0.059* | |
H14D | 0.8276 | −0.1692 | 0.5973 | 0.059* | |
C15A | −0.0805 (3) | 0.14129 (10) | 0.7568 (2) | 0.0471 (7) | |
H15A | −0.1706 | 0.1440 | 0.6993 | 0.057* | |
H15B | −0.0960 | 0.1226 | 0.8103 | 0.057* | |
C15B | 0.9600 (3) | −0.17946 (11) | 0.7478 (3) | 0.0518 (7) | |
H15C | 1.0343 | −0.1928 | 0.7258 | 0.062* | |
H15D | 1.0057 | −0.1610 | 0.8086 | 0.062* | |
C16A | 0.1110 (3) | 0.18288 (10) | 0.8865 (2) | 0.0430 (6) | |
H16A | 0.1011 | 0.1665 | 0.9454 | 0.052* | |
H16B | 0.1443 | 0.2125 | 0.9107 | 0.052* | |
C16B | 0.7485 (3) | −0.19724 (11) | 0.7989 (3) | 0.0507 (7) | |
H16C | 0.7805 | −0.1797 | 0.8626 | 0.061* | |
H16D | 0.6918 | −0.2216 | 0.8102 | 0.061* | |
C17A | 0.2196 (3) | 0.16009 (10) | 0.8477 (2) | 0.0452 (6) | |
H17A | 0.2378 | 0.1782 | 0.7942 | 0.054* | |
H17B | 0.3091 | 0.1566 | 0.9053 | 0.054* | |
C17B | 0.6572 (3) | −0.16899 (11) | 0.7092 (3) | 0.0536 (7) | |
H17C | 0.6182 | −0.1869 | 0.6465 | 0.064* | |
H17D | 0.5781 | −0.1564 | 0.7266 | 0.064* | |
C18 | 0.4855 (3) | 0.26345 (11) | 1.0572 (2) | 0.0494 (7) | |
C19 | 0.5794 (3) | 0.24896 (10) | 0.9978 (2) | 0.0433 (6) | |
H19A | 0.5355 | 0.2391 | 0.9293 | 0.052* | |
C20 | 0.7206 (3) | 0.24908 (10) | 1.0354 (2) | 0.0423 (6) | |
H20A | 0.7643 | 0.2587 | 1.1042 | 0.051* | |
C21 | 0.8157 (3) | 0.23493 (9) | 0.9759 (2) | 0.0370 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.0270 (8) | 0.0679 (12) | 0.1077 (17) | −0.0081 (8) | 0.0164 (9) | −0.0033 (11) |
F1B | 0.0281 (8) | 0.0658 (11) | 0.0788 (12) | 0.0075 (7) | 0.0157 (8) | 0.0035 (9) |
N1A | 0.0266 (10) | 0.0428 (12) | 0.0438 (11) | 0.0039 (9) | 0.0171 (9) | 0.0021 (9) |
N1B | 0.0282 (10) | 0.0453 (12) | 0.0440 (12) | −0.0031 (9) | 0.0184 (9) | −0.0002 (9) |
N2A | 0.0291 (11) | 0.0494 (13) | 0.0550 (13) | 0.0053 (10) | 0.0125 (10) | −0.0095 (10) |
N2B | 0.0445 (13) | 0.0504 (14) | 0.0729 (17) | 0.0089 (11) | 0.0374 (13) | 0.0127 (12) |
N3A | 0.0354 (12) | 0.0533 (13) | 0.0474 (13) | 0.0073 (10) | 0.0266 (10) | 0.0060 (10) |
N3B | 0.0467 (14) | 0.0501 (14) | 0.0437 (13) | 0.0078 (11) | 0.0101 (11) | −0.0015 (11) |
O1A | 0.0455 (14) | 0.0778 (17) | 0.123 (2) | 0.0236 (13) | 0.0291 (15) | 0.0061 (16) |
O1B | 0.0397 (11) | 0.0578 (12) | 0.0710 (14) | 0.0084 (9) | 0.0232 (10) | 0.0034 (10) |
O2A | 0.0723 (17) | 0.0516 (13) | 0.0682 (15) | 0.0193 (12) | 0.0280 (13) | 0.0033 (10) |
O2B | 0.0461 (13) | 0.0450 (11) | 0.0874 (17) | −0.0044 (10) | 0.0268 (12) | −0.0035 (11) |
O3A | 0.0587 (13) | 0.0401 (10) | 0.0544 (12) | 0.0000 (9) | 0.0233 (10) | −0.0015 (8) |
O3B | 0.0371 (10) | 0.0478 (11) | 0.0659 (13) | −0.0082 (9) | 0.0200 (9) | −0.0059 (9) |
O4 | 0.0453 (14) | 0.182 (3) | 0.0642 (16) | 0.0328 (18) | 0.0202 (12) | −0.0173 (18) |
O5 | 0.0514 (12) | 0.0840 (16) | 0.0499 (12) | 0.0084 (11) | 0.0284 (10) | −0.0100 (10) |
O6 | 0.0314 (10) | 0.0900 (16) | 0.0507 (12) | 0.0058 (10) | 0.0149 (9) | −0.0005 (10) |
O7 | 0.0389 (10) | 0.0634 (12) | 0.0393 (10) | 0.0067 (9) | 0.0198 (8) | −0.0006 (8) |
O8A | 0.055 (2) | 0.097 (4) | 0.092 (4) | −0.0117 (19) | 0.034 (2) | −0.029 (3) |
O9 | 0.090 (3) | 0.147 (4) | 0.129 (3) | −0.025 (2) | 0.043 (2) | −0.035 (3) |
O10A | 0.137 (10) | 0.095 (5) | 0.115 (5) | −0.020 (6) | −0.001 (5) | 0.020 (4) |
C1A | 0.0339 (13) | 0.0501 (15) | 0.0447 (14) | 0.0079 (11) | 0.0214 (11) | 0.0030 (11) |
C1B | 0.0325 (13) | 0.0502 (15) | 0.0411 (13) | 0.0030 (11) | 0.0193 (10) | 0.0020 (11) |
C2A | 0.0407 (14) | 0.0467 (15) | 0.0375 (13) | 0.0102 (12) | 0.0209 (11) | 0.0020 (10) |
C2B | 0.0333 (13) | 0.0487 (15) | 0.0348 (12) | −0.0013 (11) | 0.0186 (10) | −0.0006 (10) |
C3A | 0.0439 (14) | 0.0436 (14) | 0.0321 (12) | 0.0042 (11) | 0.0229 (11) | 0.0009 (10) |
C3B | 0.0336 (13) | 0.0477 (14) | 0.0340 (12) | −0.0039 (11) | 0.0184 (10) | −0.0022 (10) |
C4A | 0.0363 (13) | 0.0422 (13) | 0.0337 (12) | 0.0017 (11) | 0.0193 (10) | 0.0003 (10) |
C4B | 0.0310 (12) | 0.0465 (14) | 0.0319 (12) | −0.0005 (10) | 0.0183 (10) | 0.0000 (10) |
C5A | 0.0369 (13) | 0.0434 (14) | 0.0440 (14) | −0.0050 (11) | 0.0197 (11) | −0.0044 (11) |
C5B | 0.0288 (12) | 0.0509 (15) | 0.0407 (13) | −0.0040 (11) | 0.0167 (10) | −0.0015 (11) |
C6A | 0.0258 (12) | 0.0528 (15) | 0.0483 (15) | −0.0050 (11) | 0.0161 (11) | −0.0032 (12) |
C6B | 0.0255 (12) | 0.0541 (15) | 0.0447 (14) | 0.0049 (11) | 0.0174 (10) | 0.0041 (11) |
C7A | 0.0274 (12) | 0.0488 (14) | 0.0380 (13) | 0.0028 (11) | 0.0156 (10) | −0.0034 (10) |
C7B | 0.0347 (13) | 0.0469 (14) | 0.0418 (13) | 0.0056 (11) | 0.0221 (11) | 0.0033 (11) |
C8A | 0.0292 (12) | 0.0413 (13) | 0.0431 (13) | 0.0003 (10) | 0.0188 (10) | 0.0001 (10) |
C8B | 0.0364 (13) | 0.0457 (14) | 0.0443 (14) | −0.0018 (11) | 0.0197 (11) | 0.0001 (11) |
C9A | 0.0279 (12) | 0.0427 (13) | 0.0347 (12) | 0.0003 (10) | 0.0178 (9) | −0.0004 (10) |
C9B | 0.0295 (12) | 0.0468 (14) | 0.0342 (12) | −0.0003 (10) | 0.0174 (10) | −0.0001 (10) |
C10A | 0.0323 (13) | 0.0461 (14) | 0.0569 (16) | −0.0026 (11) | 0.0226 (12) | 0.0031 (12) |
C10B | 0.0347 (14) | 0.0562 (17) | 0.0626 (18) | −0.0076 (13) | 0.0208 (13) | −0.0064 (14) |
C11A | 0.0447 (16) | 0.0471 (15) | 0.078 (2) | −0.0051 (13) | 0.0340 (15) | −0.0081 (14) |
C11B | 0.0557 (19) | 0.066 (2) | 0.073 (2) | −0.0101 (16) | 0.0290 (17) | 0.0055 (16) |
C12A | 0.0390 (15) | 0.0593 (18) | 0.0658 (19) | −0.0035 (13) | 0.0218 (14) | −0.0081 (14) |
C12B | 0.0364 (15) | 0.066 (2) | 0.078 (2) | −0.0054 (14) | 0.0225 (15) | 0.0003 (16) |
C13A | 0.0547 (18) | 0.0531 (18) | 0.0574 (18) | 0.0181 (15) | 0.0280 (15) | 0.0013 (13) |
C13B | 0.0397 (14) | 0.0502 (15) | 0.0432 (14) | 0.0054 (12) | 0.0228 (11) | 0.0003 (11) |
C14A | 0.0321 (13) | 0.0587 (17) | 0.0447 (14) | 0.0079 (12) | 0.0107 (11) | −0.0046 (12) |
C14B | 0.0426 (15) | 0.0527 (16) | 0.0625 (18) | 0.0084 (13) | 0.0304 (14) | 0.0030 (13) |
C15A | 0.0302 (12) | 0.0582 (17) | 0.0552 (16) | 0.0036 (12) | 0.0174 (12) | 0.0022 (13) |
C15B | 0.0367 (14) | 0.0596 (18) | 0.0591 (17) | 0.0040 (13) | 0.0161 (13) | −0.0038 (14) |
C16A | 0.0361 (13) | 0.0506 (15) | 0.0468 (14) | 0.0035 (12) | 0.0200 (12) | −0.0018 (12) |
C16B | 0.0526 (17) | 0.0524 (16) | 0.0553 (17) | 0.0021 (13) | 0.0290 (14) | 0.0016 (13) |
C17A | 0.0322 (13) | 0.0478 (15) | 0.0585 (17) | 0.0010 (12) | 0.0192 (12) | −0.0053 (12) |
C17B | 0.0429 (16) | 0.0528 (17) | 0.072 (2) | 0.0039 (13) | 0.0290 (15) | 0.0098 (15) |
C18 | 0.0398 (15) | 0.0657 (18) | 0.0488 (16) | 0.0024 (13) | 0.0228 (13) | −0.0068 (13) |
C19 | 0.0362 (14) | 0.0554 (16) | 0.0434 (14) | 0.0035 (12) | 0.0201 (11) | −0.0018 (12) |
C20 | 0.0379 (14) | 0.0529 (15) | 0.0423 (13) | 0.0026 (12) | 0.0214 (11) | −0.0037 (11) |
C21 | 0.0312 (12) | 0.0431 (13) | 0.0400 (13) | 0.0054 (10) | 0.0164 (10) | 0.0056 (10) |
Geometric parameters (Å, º) top
F1A—C6A | 1.361 (3) | C4B—C5B | 1.407 (4) |
F1B—C6B | 1.364 (3) | C4B—C9B | 1.408 (4) |
N1A—C1A | 1.344 (3) | C5A—C6A | 1.348 (4) |
N1A—C9A | 1.401 (3) | C5A—H5AA | 0.9300 |
N1A—C10A | 1.450 (4) | C5B—C6B | 1.350 (4) |
N1B—C1B | 1.336 (4) | C5B—H5BA | 0.9300 |
N1B—C9B | 1.405 (3) | C6A—C7A | 1.409 (4) |
N1B—C10B | 1.457 (4) | C6B—C7B | 1.413 (4) |
N2A—C7A | 1.379 (3) | C7A—C8A | 1.398 (4) |
N2A—C17A | 1.451 (4) | C7B—C8B | 1.403 (4) |
N2A—C14A | 1.461 (3) | C8A—C9A | 1.396 (4) |
N2B—C7B | 1.369 (4) | C8A—H8AA | 0.9300 |
N2B—C17B | 1.450 (4) | C8B—C9B | 1.391 (4) |
N2B—C14B | 1.474 (4) | C8B—H8BA | 0.9300 |
N3A—C15A | 1.483 (4) | C10A—C12A | 1.478 (4) |
N3A—C16A | 1.492 (4) | C10A—C11A | 1.489 (5) |
N3A—H3A | 0.873 (19) | C10A—H10A | 0.9800 |
N3A—H3B | 0.872 (19) | C10B—C12B | 1.475 (4) |
N3B—C16B | 1.489 (4) | C10B—C11B | 1.483 (5) |
N3B—C15B | 1.495 (4) | C10B—H10B | 0.9800 |
N3B—H3C | 0.880 (19) | C11A—C12A | 1.485 (4) |
N3B—H3D | 0.886 (19) | C11A—H11A | 0.9700 |
O1A—C13A | 1.215 (4) | C11A—H11B | 0.9700 |
O1B—C13B | 1.215 (3) | C11B—C12B | 1.502 (5) |
O2A—C13A | 1.320 (4) | C11B—H11C | 0.9700 |
O2A—H2A | 0.93 (5) | C11B—H11D | 0.9700 |
O2B—C13B | 1.323 (4) | C12A—H12C | 0.9700 |
O2B—H2B | 0.84 (6) | C12A—H12D | 0.9700 |
O3A—C3A | 1.265 (3) | C12B—H12A | 0.9700 |
O3B—C3B | 1.270 (3) | C12B—H12B | 0.9700 |
O4—C18 | 1.244 (4) | C14A—C15A | 1.506 (4) |
O5—C18 | 1.250 (4) | C14A—H14A | 0.9700 |
O6—C21 | 1.257 (3) | C14A—H14B | 0.9700 |
O7—C21 | 1.262 (3) | C14B—C15B | 1.497 (4) |
O8A—H8A | 0.89 (2) | C14B—H14C | 0.9700 |
O8A—H8B | 0.888 (19) | C14B—H14D | 0.9700 |
O8B—H8A | 0.91 (2) | C15A—H15A | 0.9700 |
O8B—H8B | 0.913 (19) | C15A—H15B | 0.9700 |
O9—H9A | 0.95 (2) | C15B—H15C | 0.9700 |
O9—H9B | 0.95 (2) | C15B—H15D | 0.9700 |
O10A—H10C | 0.90 (2) | C16A—C17A | 1.515 (4) |
O10A—H10D | 0.90 (2) | C16A—H16A | 0.9700 |
O10B—H10C | 0.90 (2) | C16A—H16B | 0.9700 |
O10B—H10D | 0.90 (2) | C16B—C17B | 1.510 (5) |
C1A—C2A | 1.368 (4) | C16B—H16C | 0.9700 |
C1A—H1AA | 0.9300 | C16B—H16D | 0.9700 |
C1B—C2B | 1.373 (4) | C17A—H17A | 0.9700 |
C1B—H1BA | 0.9300 | C17A—H17B | 0.9700 |
C2A—C3A | 1.438 (4) | C17B—H17C | 0.9700 |
C2A—C13A | 1.481 (4) | C17B—H17D | 0.9700 |
C2B—C3B | 1.431 (4) | C18—C19 | 1.487 (4) |
C2B—C13B | 1.482 (4) | C19—C20 | 1.320 (4) |
C3A—C4A | 1.437 (4) | C19—H19A | 0.9300 |
C3B—C4B | 1.438 (4) | C20—C21 | 1.495 (4) |
C4A—C9A | 1.394 (4) | C20—H20A | 0.9300 |
C4A—C5A | 1.411 (4) | | |
| | | |
C1A—N1A—C9A | 119.6 (2) | N1B—C10B—H10B | 115.1 |
C1A—N1A—C10A | 120.9 (2) | C12B—C10B—H10B | 115.1 |
C9A—N1A—C10A | 119.4 (2) | C11B—C10B—H10B | 115.1 |
C1B—N1B—C9B | 119.4 (2) | C12A—C11A—C10A | 59.6 (2) |
C1B—N1B—C10B | 119.9 (2) | C12A—C11A—H11A | 117.8 |
C9B—N1B—C10B | 120.4 (2) | C10A—C11A—H11A | 117.8 |
C7A—N2A—C17A | 121.3 (2) | C12A—C11A—H11B | 117.8 |
C7A—N2A—C14A | 123.2 (2) | C10A—C11A—H11B | 117.8 |
C17A—N2A—C14A | 111.5 (2) | H11A—C11A—H11B | 114.9 |
C7B—N2B—C17B | 121.7 (2) | C10B—C11B—C12B | 59.2 (2) |
C7B—N2B—C14B | 123.2 (2) | C10B—C11B—H11C | 117.9 |
C17B—N2B—C14B | 111.9 (2) | C12B—C11B—H11C | 117.9 |
C15A—N3A—C16A | 111.1 (2) | C10B—C11B—H11D | 117.9 |
C15A—N3A—H3A | 108 (3) | C12B—C11B—H11D | 117.9 |
C16A—N3A—H3A | 107 (3) | H11C—C11B—H11D | 115.0 |
C15A—N3A—H3B | 108 (2) | C10A—C12A—C11A | 60.3 (2) |
C16A—N3A—H3B | 109 (2) | C10A—C12A—H12C | 117.7 |
H3A—N3A—H3B | 113 (4) | C11A—C12A—H12C | 117.7 |
C16B—N3B—C15B | 112.4 (2) | C10A—C12A—H12D | 117.7 |
C16B—N3B—H3C | 113 (2) | C11A—C12A—H12D | 117.7 |
C15B—N3B—H3C | 106 (2) | H12C—C12A—H12D | 114.9 |
C16B—N3B—H3D | 114 (3) | C10B—C12B—C11B | 59.7 (2) |
C15B—N3B—H3D | 106 (3) | C10B—C12B—H12A | 117.8 |
H3C—N3B—H3D | 104 (4) | C11B—C12B—H12A | 117.8 |
C13A—O2A—H2A | 108 (3) | C10B—C12B—H12B | 117.8 |
C13B—O2B—H2B | 113 (4) | C11B—C12B—H12B | 117.8 |
H8A—O8A—H8B | 84 (5) | H12A—C12B—H12B | 114.9 |
H8A—O8B—H8B | 82 (5) | O1A—C13A—O2A | 120.9 (3) |
H9A—O9—H9B | 131 (6) | O1A—C13A—C2A | 123.3 (3) |
H10C—O10A—H10D | 85 (10) | O2A—C13A—C2A | 115.8 (3) |
H10C—O10B—H10D | 85 (10) | O1B—C13B—O2B | 120.9 (3) |
N1A—C1A—C2A | 124.0 (3) | O1B—C13B—C2B | 123.2 (3) |
N1A—C1A—H1AA | 118.0 | O2B—C13B—C2B | 115.9 (2) |
C2A—C1A—H1AA | 118.0 | N2A—C14A—C15A | 109.9 (2) |
N1B—C1B—C2B | 124.7 (2) | N2A—C14A—H14A | 109.7 |
N1B—C1B—H1BA | 117.6 | C15A—C14A—H14A | 109.7 |
C2B—C1B—H1BA | 117.6 | N2A—C14A—H14B | 109.7 |
C1A—C2A—C3A | 119.6 (2) | C15A—C14A—H14B | 109.7 |
C1A—C2A—C13A | 119.2 (3) | H14A—C14A—H14B | 108.2 |
C3A—C2A—C13A | 121.2 (3) | N2B—C14B—C15B | 109.9 (3) |
C1B—C2B—C3B | 119.3 (2) | N2B—C14B—H14C | 109.7 |
C1B—C2B—C13B | 118.5 (2) | C15B—C14B—H14C | 109.7 |
C3B—C2B—C13B | 122.2 (2) | N2B—C14B—H14D | 109.7 |
O3A—C3A—C4A | 122.1 (3) | C15B—C14B—H14D | 109.7 |
O3A—C3A—C2A | 122.1 (2) | H14C—C14B—H14D | 108.2 |
C4A—C3A—C2A | 115.9 (2) | N3A—C15A—C14A | 109.4 (2) |
O3B—C3B—C2B | 122.1 (2) | N3A—C15A—H15A | 109.8 |
O3B—C3B—C4B | 121.6 (2) | C14A—C15A—H15A | 109.8 |
C2B—C3B—C4B | 116.2 (2) | N3A—C15A—H15B | 109.8 |
C9A—C4A—C5A | 117.8 (2) | C14A—C15A—H15B | 109.8 |
C9A—C4A—C3A | 121.9 (2) | H15A—C15A—H15B | 108.2 |
C5A—C4A—C3A | 120.3 (2) | N3B—C15B—C14B | 110.4 (2) |
C5B—C4B—C9B | 118.0 (2) | N3B—C15B—H15C | 109.6 |
C5B—C4B—C3B | 120.4 (2) | C14B—C15B—H15C | 109.6 |
C9B—C4B—C3B | 121.6 (2) | N3B—C15B—H15D | 109.6 |
C6A—C5A—C4A | 120.0 (2) | C14B—C15B—H15D | 109.6 |
C6A—C5A—H5AA | 120.0 | H15C—C15B—H15D | 108.1 |
C4A—C5A—H5AA | 120.0 | N3A—C16A—C17A | 110.6 (2) |
C6B—C5B—C4B | 120.1 (2) | N3A—C16A—H16A | 109.5 |
C6B—C5B—H5BA | 120.0 | C17A—C16A—H16A | 109.5 |
C4B—C5B—H5BA | 120.0 | N3A—C16A—H16B | 109.5 |
C5A—C6A—F1A | 117.3 (2) | C17A—C16A—H16B | 109.5 |
C5A—C6A—C7A | 124.1 (2) | H16A—C16A—H16B | 108.1 |
F1A—C6A—C7A | 118.6 (2) | N3B—C16B—C17B | 111.0 (3) |
C5B—C6B—F1B | 118.5 (2) | N3B—C16B—H16C | 109.4 |
C5B—C6B—C7B | 123.7 (2) | C17B—C16B—H16C | 109.4 |
F1B—C6B—C7B | 117.6 (2) | N3B—C16B—H16D | 109.4 |
N2A—C7A—C8A | 121.8 (2) | C17B—C16B—H16D | 109.4 |
N2A—C7A—C6A | 122.4 (2) | H16C—C16B—H16D | 108.0 |
C8A—C7A—C6A | 115.7 (2) | N2A—C17A—C16A | 110.1 (2) |
N2B—C7B—C8B | 122.3 (3) | N2A—C17A—H17A | 109.6 |
N2B—C7B—C6B | 121.3 (2) | C16A—C17A—H17A | 109.6 |
C8B—C7B—C6B | 116.2 (2) | N2A—C17A—H17B | 109.6 |
C9A—C8A—C7A | 121.3 (2) | C16A—C17A—H17B | 109.6 |
C9A—C8A—H8AA | 119.4 | H17A—C17A—H17B | 108.1 |
C7A—C8A—H8AA | 119.4 | N2B—C17B—C16B | 108.6 (3) |
C9B—C8B—C7B | 121.0 (2) | N2B—C17B—H17C | 110.0 |
C9B—C8B—H8BA | 119.5 | C16B—C17B—H17C | 110.0 |
C7B—C8B—H8BA | 119.5 | N2B—C17B—H17D | 110.0 |
C4A—C9A—C8A | 121.1 (2) | C16B—C17B—H17D | 110.0 |
C4A—C9A—N1A | 119.0 (2) | H17C—C17B—H17D | 108.3 |
C8A—C9A—N1A | 119.9 (2) | O4—C18—O5 | 124.1 (3) |
C8B—C9B—N1B | 120.2 (2) | O4—C18—C19 | 116.8 (3) |
C8B—C9B—C4B | 121.0 (2) | O5—C18—C19 | 119.0 (3) |
N1B—C9B—C4B | 118.8 (2) | C20—C19—C18 | 124.6 (3) |
N1A—C10A—C12A | 120.5 (3) | C20—C19—H19A | 117.7 |
N1A—C10A—C11A | 119.4 (2) | C18—C19—H19A | 117.7 |
C12A—C10A—C11A | 60.0 (2) | C19—C20—C21 | 124.9 (3) |
N1A—C10A—H10A | 115.3 | C19—C20—H20A | 117.5 |
C12A—C10A—H10A | 115.3 | C21—C20—H20A | 117.5 |
C11A—C10A—H10A | 115.3 | O6—C21—O7 | 123.0 (2) |
N1B—C10B—C12B | 119.7 (3) | O6—C21—C20 | 117.3 (2) |
N1B—C10B—C11B | 120.0 (3) | O7—C21—C20 | 119.7 (2) |
C12B—C10B—C11B | 61.0 (2) | | |
Crystal data top
C17H19FN3O3·C4H3O4 | F(000) = 936 |
Mr = 447.42 | Dx = 1.416 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 13.956 (4) Å | Cell parameters from 3531 reflections |
b = 10.459 (4) Å | θ = 3.3–72.4° |
c = 15.184 (5) Å | µ = 0.96 mm−1 |
β = 108.765 (6)° | T = 293 K |
V = 2098.5 (12) Å3 | Prism, colorless |
Z = 4 | 0.75 × 0.65 × 0.30 mm |
Data collection top
CCD diffractometer | 4083 independent reflections |
Radiation source: fine-focus sealed tube | 3531 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.047 |
Detector resolution: 0 pixels mm-1 | θmax = 72.4°, θmin = 3.3° |
ωκ scans | h = −16→17 |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | k = −12→12 |
Tmin = 0.707, Tmax = 1.000 | l = −18→13 |
20341 measured reflections | |
Refinement top
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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1645P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4083 reflections | Δρmax = 0.22 e Å−3 |
311 parameters | Δρmin = −0.19 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0054 (6) |
Crystal data top
C17H19FN3O3·C4H3O4 | V = 2098.5 (12) Å3 |
Mr = 447.42 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 13.956 (4) Å | µ = 0.96 mm−1 |
b = 10.459 (4) Å | T = 293 K |
c = 15.184 (5) Å | 0.75 × 0.65 × 0.30 mm |
β = 108.765 (6)° | |
Data collection top
CCD diffractometer | 4083 independent reflections |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | 3531 reflections with I > 2σ(I) |
Tmin = 0.707, Tmax = 1.000 | Rint = 0.047 |
20341 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 2 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.22 e Å−3 |
4083 reflections | Δρmin = −0.19 e Å−3 |
311 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.42541 (10) | 0.70397 (15) | 0.14347 (9) | 0.0428 (3) | |
H1A | 0.4019 | 0.7838 | 0.1541 | 0.051* | |
C2 | 0.35945 (10) | 0.60340 (15) | 0.12676 (9) | 0.0420 (3) | |
C3 | 0.39203 (9) | 0.47823 (14) | 0.11114 (9) | 0.0397 (3) | |
C4 | 0.49749 (9) | 0.46793 (13) | 0.11670 (8) | 0.0368 (3) | |
C5 | 0.53786 (10) | 0.34854 (13) | 0.10474 (9) | 0.0412 (3) | |
H5A | 0.4971 | 0.2760 | 0.0940 | 0.049* | |
C6 | 0.63622 (10) | 0.33885 (13) | 0.10881 (10) | 0.0414 (3) | |
C7 | 0.70340 (9) | 0.44440 (13) | 0.12821 (8) | 0.0360 (3) | |
C8 | 0.66362 (9) | 0.56165 (13) | 0.14088 (8) | 0.0370 (3) | |
H8A | 0.7055 | 0.6331 | 0.1544 | 0.044* | |
C9 | 0.56142 (9) | 0.57471 (13) | 0.13375 (8) | 0.0355 (3) | |
C10 | 0.58809 (11) | 0.80637 (14) | 0.17056 (10) | 0.0462 (3) | |
H10A | 0.6313 | 0.8105 | 0.2357 | 0.055* | |
C11 | 0.63167 (15) | 0.86295 (18) | 0.10240 (14) | 0.0656 (5) | |
H11A | 0.6146 | 0.8235 | 0.0415 | 0.079* | |
H11B | 0.6996 | 0.8979 | 0.1258 | 0.079* | |
C12 | 0.54931 (15) | 0.93130 (18) | 0.12684 (15) | 0.0697 (5) | |
H12A | 0.5675 | 1.0074 | 0.1651 | 0.084* | |
H12B | 0.4825 | 0.9331 | 0.0807 | 0.084* | |
C13 | 0.25457 (11) | 0.62908 (17) | 0.12741 (11) | 0.0514 (4) | |
C14 | 0.86372 (10) | 0.33388 (14) | 0.19697 (10) | 0.0435 (3) | |
H14A | 0.8237 | 0.2576 | 0.1953 | 0.052* | |
H14B | 0.8827 | 0.3690 | 0.2594 | 0.052* | |
C15 | 0.95734 (10) | 0.29985 (14) | 0.17335 (11) | 0.0473 (3) | |
H15A | 0.9975 | 0.2392 | 0.2186 | 0.057* | |
H15B | 0.9382 | 0.2596 | 0.1126 | 0.057* | |
C16 | 0.95727 (10) | 0.51492 (14) | 0.10897 (9) | 0.0424 (3) | |
H16A | 0.9393 | 0.4845 | 0.0454 | 0.051* | |
H16B | 0.9971 | 0.5922 | 0.1140 | 0.051* | |
C17 | 0.86194 (10) | 0.54488 (13) | 0.13200 (10) | 0.0406 (3) | |
H17A | 0.8797 | 0.5835 | 0.1933 | 0.049* | |
H17B | 0.8212 | 0.6056 | 0.0872 | 0.049* | |
C18 | 0.84463 (11) | 0.69072 (15) | 0.39068 (10) | 0.0467 (3) | |
C19 | 0.81616 (15) | 0.56073 (18) | 0.41281 (11) | 0.0630 (5) | |
H19A | 0.7798 | 0.5128 | 0.3613 | 0.076* | |
C20 | 0.83402 (16) | 0.50133 (17) | 0.49404 (12) | 0.0677 (5) | |
H20A | 0.8089 | 0.4184 | 0.4901 | 0.081* | |
C21 | 0.88788 (12) | 0.54675 (15) | 0.59015 (11) | 0.0511 (4) | |
N1 | 0.52244 (8) | 0.69460 (11) | 0.14555 (8) | 0.0395 (3) | |
N2 | 0.80343 (8) | 0.42816 (11) | 0.13010 (7) | 0.0378 (3) | |
N3 | 1.01862 (8) | 0.41604 (12) | 0.17304 (9) | 0.0416 (3) | |
H3A | 1.0735 (18) | 0.391 (2) | 0.1561 (14) | 0.072 (6)* | |
H3B | 1.0470 (15) | 0.4516 (19) | 0.2321 (14) | 0.060 (5)* | |
O1 | 0.22431 (10) | 0.73433 (14) | 0.13770 (11) | 0.0751 (4) | |
O2 | 0.19571 (8) | 0.52629 (14) | 0.11620 (9) | 0.0621 (3) | |
H2A | 0.235 (2) | 0.452 (3) | 0.113 (2) | 0.116 (10)* | |
O3 | 0.33433 (7) | 0.38227 (11) | 0.09509 (8) | 0.0523 (3) | |
O4 | 0.89960 (10) | 0.76240 (12) | 0.45640 (8) | 0.0590 (3) | |
H4A | 0.910 (3) | 0.726 (4) | 0.5073 (15) | 0.071 (16)* | 0.57 (7) |
O5 | 0.81670 (8) | 0.72729 (13) | 0.30984 (7) | 0.0588 (3) | |
O6 | 0.92891 (11) | 0.65675 (12) | 0.60334 (8) | 0.0669 (4) | |
H6A | 0.920 (3) | 0.690 (4) | 0.5516 (16) | 0.054 (18)* | 0.43 (7) |
O7 | 0.88970 (12) | 0.47528 (12) | 0.65499 (8) | 0.0713 (4) | |
F1 | 0.67006 (7) | 0.22377 (9) | 0.09064 (8) | 0.0606 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0308 (7) | 0.0496 (8) | 0.0482 (7) | 0.0071 (6) | 0.0129 (5) | 0.0012 (6) |
C2 | 0.0267 (6) | 0.0543 (8) | 0.0455 (7) | 0.0046 (6) | 0.0124 (5) | 0.0054 (6) |
C3 | 0.0259 (6) | 0.0509 (8) | 0.0412 (6) | −0.0004 (5) | 0.0092 (5) | 0.0054 (5) |
C4 | 0.0234 (6) | 0.0453 (7) | 0.0397 (6) | −0.0014 (5) | 0.0074 (4) | 0.0013 (5) |
C5 | 0.0278 (6) | 0.0410 (7) | 0.0524 (7) | −0.0051 (5) | 0.0095 (5) | −0.0026 (6) |
C6 | 0.0297 (7) | 0.0384 (7) | 0.0546 (7) | 0.0006 (5) | 0.0115 (5) | −0.0038 (6) |
C7 | 0.0226 (6) | 0.0429 (7) | 0.0409 (6) | −0.0003 (5) | 0.0078 (4) | −0.0002 (5) |
C8 | 0.0235 (6) | 0.0412 (7) | 0.0443 (6) | −0.0034 (5) | 0.0082 (5) | −0.0033 (5) |
C9 | 0.0249 (6) | 0.0415 (7) | 0.0377 (6) | 0.0009 (5) | 0.0069 (4) | −0.0016 (5) |
C10 | 0.0361 (7) | 0.0419 (7) | 0.0553 (7) | −0.0019 (6) | 0.0074 (6) | −0.0076 (6) |
C11 | 0.0570 (10) | 0.0607 (10) | 0.0797 (11) | −0.0195 (8) | 0.0228 (8) | −0.0056 (9) |
C12 | 0.0556 (10) | 0.0460 (9) | 0.0973 (13) | −0.0008 (8) | 0.0103 (9) | 0.0051 (9) |
C13 | 0.0312 (7) | 0.0664 (10) | 0.0590 (8) | 0.0087 (7) | 0.0177 (6) | 0.0086 (7) |
C14 | 0.0293 (6) | 0.0453 (7) | 0.0557 (7) | 0.0025 (5) | 0.0132 (5) | 0.0094 (6) |
C15 | 0.0295 (7) | 0.0404 (7) | 0.0710 (9) | 0.0034 (5) | 0.0147 (6) | 0.0052 (6) |
C16 | 0.0271 (6) | 0.0496 (8) | 0.0509 (7) | 0.0007 (6) | 0.0133 (5) | 0.0077 (6) |
C17 | 0.0252 (6) | 0.0397 (7) | 0.0569 (7) | 0.0011 (5) | 0.0133 (5) | 0.0040 (6) |
C18 | 0.0372 (7) | 0.0554 (8) | 0.0480 (7) | −0.0050 (6) | 0.0144 (6) | −0.0055 (6) |
C19 | 0.0721 (11) | 0.0582 (10) | 0.0508 (8) | −0.0218 (8) | 0.0088 (7) | −0.0129 (7) |
C20 | 0.0863 (13) | 0.0457 (9) | 0.0624 (10) | −0.0184 (9) | 0.0119 (9) | −0.0056 (7) |
C21 | 0.0527 (9) | 0.0420 (8) | 0.0539 (8) | 0.0040 (6) | 0.0105 (6) | −0.0001 (6) |
N1 | 0.0271 (5) | 0.0419 (6) | 0.0476 (6) | 0.0012 (4) | 0.0093 (4) | −0.0028 (5) |
N2 | 0.0225 (5) | 0.0398 (6) | 0.0506 (6) | 0.0012 (4) | 0.0113 (4) | 0.0027 (5) |
N3 | 0.0242 (5) | 0.0447 (6) | 0.0552 (7) | 0.0028 (5) | 0.0119 (5) | 0.0014 (5) |
O1 | 0.0483 (7) | 0.0740 (9) | 0.1130 (10) | 0.0182 (6) | 0.0401 (7) | 0.0054 (8) |
O2 | 0.0294 (5) | 0.0746 (8) | 0.0861 (8) | −0.0006 (5) | 0.0241 (5) | 0.0051 (6) |
O3 | 0.0279 (5) | 0.0550 (6) | 0.0736 (7) | −0.0073 (4) | 0.0160 (4) | 0.0026 (5) |
O4 | 0.0694 (8) | 0.0556 (7) | 0.0492 (6) | −0.0213 (6) | 0.0149 (5) | −0.0050 (5) |
O5 | 0.0467 (6) | 0.0764 (8) | 0.0504 (6) | −0.0080 (5) | 0.0116 (5) | 0.0025 (5) |
O6 | 0.0860 (9) | 0.0551 (7) | 0.0489 (6) | −0.0196 (6) | 0.0069 (6) | −0.0028 (5) |
O7 | 0.0921 (10) | 0.0515 (7) | 0.0596 (7) | −0.0039 (6) | 0.0095 (6) | 0.0101 (5) |
F1 | 0.0386 (5) | 0.0415 (5) | 0.1010 (7) | 0.0000 (4) | 0.0214 (4) | −0.0153 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.3479 (18) | C14—N2 | 1.4702 (17) |
C1—C2 | 1.367 (2) | C14—C15 | 1.505 (2) |
C1—H1A | 0.9300 | C14—H14A | 0.9700 |
C2—C3 | 1.430 (2) | C14—H14B | 0.9700 |
C2—C13 | 1.4913 (19) | C15—N3 | 1.4869 (19) |
C3—O3 | 1.2605 (18) | C15—H15A | 0.9700 |
C3—C4 | 1.4508 (18) | C15—H15B | 0.9700 |
C4—C9 | 1.4006 (19) | C16—N3 | 1.4876 (18) |
C4—C5 | 1.406 (2) | C16—C17 | 1.5132 (18) |
C5—C6 | 1.358 (2) | C16—H16A | 0.9700 |
C5—H5A | 0.9300 | C16—H16B | 0.9700 |
C6—F1 | 1.3534 (16) | C17—N2 | 1.4638 (18) |
C6—C7 | 1.4166 (19) | C17—H17A | 0.9700 |
C7—C8 | 1.3849 (19) | C17—H17B | 0.9700 |
C7—N2 | 1.3974 (16) | C18—O5 | 1.2235 (19) |
C8—C9 | 1.4018 (18) | C18—O4 | 1.2860 (18) |
C8—H8A | 0.9300 | C18—C19 | 1.485 (2) |
C9—N1 | 1.4012 (18) | C19—C20 | 1.331 (3) |
C10—N1 | 1.4582 (19) | C19—H19A | 0.9300 |
C10—C11 | 1.482 (3) | C20—C21 | 1.488 (2) |
C10—C12 | 1.487 (2) | C20—H20A | 0.9300 |
C10—H10A | 0.9800 | C21—O7 | 1.230 (2) |
C11—C12 | 1.498 (3) | C21—O6 | 1.272 (2) |
C11—H11A | 0.9700 | N3—H3A | 0.92 (2) |
C11—H11B | 0.9700 | N3—H3B | 0.93 (2) |
C12—H12A | 0.9700 | O2—H2A | 0.96 (3) |
C12—H12B | 0.9700 | O4—H4A | 0.830 (10) |
C13—O1 | 1.207 (2) | O6—H6A | 0.829 (10) |
C13—O2 | 1.330 (2) | | |
| | | |
N1—C1—C2 | 124.05 (13) | C15—C14—H14A | 109.7 |
N1—C1—H1A | 118.0 | N2—C14—H14B | 109.7 |
C2—C1—H1A | 118.0 | C15—C14—H14B | 109.7 |
C1—C2—C3 | 120.28 (12) | H14A—C14—H14B | 108.2 |
C1—C2—C13 | 117.64 (14) | N3—C15—C14 | 110.60 (12) |
C3—C2—C13 | 122.07 (13) | N3—C15—H15A | 109.5 |
O3—C3—C2 | 122.91 (12) | C14—C15—H15A | 109.5 |
O3—C3—C4 | 121.68 (13) | N3—C15—H15B | 109.5 |
C2—C3—C4 | 115.39 (12) | C14—C15—H15B | 109.5 |
C9—C4—C5 | 118.31 (12) | H15A—C15—H15B | 108.1 |
C9—C4—C3 | 121.71 (12) | N3—C16—C17 | 110.89 (11) |
C5—C4—C3 | 119.98 (12) | N3—C16—H16A | 109.5 |
C6—C5—C4 | 120.12 (12) | C17—C16—H16A | 109.5 |
C6—C5—H5A | 119.9 | N3—C16—H16B | 109.5 |
C4—C5—H5A | 119.9 | C17—C16—H16B | 109.5 |
F1—C6—C5 | 118.10 (12) | H16A—C16—H16B | 108.0 |
F1—C6—C7 | 118.98 (12) | N2—C17—C16 | 110.43 (11) |
C5—C6—C7 | 122.89 (12) | N2—C17—H17A | 109.6 |
C8—C7—N2 | 123.18 (11) | C16—C17—H17A | 109.6 |
C8—C7—C6 | 116.79 (11) | N2—C17—H17B | 109.6 |
N2—C7—C6 | 119.97 (12) | C16—C17—H17B | 109.6 |
C7—C8—C9 | 121.27 (12) | H17A—C17—H17B | 108.1 |
C7—C8—H8A | 119.4 | O5—C18—O4 | 120.95 (15) |
C9—C8—H8A | 119.4 | O5—C18—C19 | 119.42 (13) |
C4—C9—N1 | 119.13 (11) | O4—C18—C19 | 119.63 (13) |
C4—C9—C8 | 120.56 (12) | C20—C19—C18 | 130.78 (14) |
N1—C9—C8 | 120.30 (11) | C20—C19—H19A | 114.6 |
N1—C10—C11 | 120.19 (13) | C18—C19—H19A | 114.6 |
N1—C10—C12 | 118.71 (13) | C19—C20—C21 | 130.14 (16) |
C11—C10—C12 | 60.61 (13) | C19—C20—H20A | 114.9 |
N1—C10—H10A | 115.4 | C21—C20—H20A | 114.9 |
C11—C10—H10A | 115.4 | O7—C21—O6 | 122.10 (15) |
C12—C10—H10A | 115.4 | O7—C21—C20 | 117.70 (15) |
C10—C11—C12 | 59.84 (12) | O6—C21—C20 | 120.19 (14) |
C10—C11—H11A | 117.8 | C1—N1—C9 | 119.38 (12) |
C12—C11—H11A | 117.8 | C1—N1—C10 | 119.35 (12) |
C10—C11—H11B | 117.8 | C9—N1—C10 | 120.90 (11) |
C12—C11—H11B | 117.8 | C7—N2—C17 | 116.51 (11) |
H11A—C11—H11B | 114.9 | C7—N2—C14 | 116.21 (10) |
C10—C12—C11 | 59.54 (12) | C17—N2—C14 | 110.73 (10) |
C10—C12—H12A | 117.8 | C15—N3—C16 | 111.08 (11) |
C11—C12—H12A | 117.8 | C15—N3—H3A | 107.7 (14) |
C10—C12—H12B | 117.8 | C16—N3—H3A | 111.5 (13) |
C11—C12—H12B | 117.8 | C15—N3—H3B | 112.9 (12) |
H12A—C12—H12B | 115.0 | C16—N3—H3B | 109.2 (12) |
O1—C13—O2 | 121.74 (14) | H3A—N3—H3B | 104.2 (18) |
O1—C13—C2 | 123.38 (16) | C13—O2—H2A | 109.0 (19) |
O2—C13—C2 | 114.87 (14) | C18—O4—H4A | 110 (3) |
N2—C14—C15 | 110.00 (11) | C21—O6—H6A | 108 (3) |
N2—C14—H14A | 109.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O5i | 0.92 (2) | 2.25 (2) | 2.9770 (18) | 135.7 (18) |
N3—H3A···O4i | 0.92 (2) | 2.30 (2) | 3.0317 (18) | 136.1 (18) |
N3—H3A···O2ii | 0.92 (2) | 2.43 (2) | 3.0911 (17) | 128.4 (18) |
N3—H3B···O7iii | 0.93 (2) | 1.82 (2) | 2.7564 (19) | 175.8 (18) |
O2—H2A···O3 | 0.96 (3) | 1.67 (3) | 2.5521 (17) | 151 (3) |
O4—H4A···O6 | 0.83 (1) | 1.57 (1) | 2.4039 (17) | 179 (5) |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+2, −y+1, −z+1. |
Crystal data top
C6H6O7·2(C17H19FN3O3)·C4H8O·3(H2O) | Z = 2 |
Mr = 980.96 | F(000) = 1036 |
Triclinic, P1 | Dx = 1.403 Mg m−3 |
a = 10.225 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 13.8350 (6) Å | Cell parameters from 7818 reflections |
c = 18.560 (7) Å | θ = 4.7–66.0° |
α = 72.83 (4)° | µ = 0.96 mm−1 |
β = 86.82 (6)° | T = 293 K |
γ = 68.03 (5)° | Prism, colorless |
V = 2321.9 (10) Å3 | 0.64 × 0.43 × 0.07 mm |
Data collection top
CCD diffractometer | 7818 independent reflections |
Radiation source: fine-focus sealed tube | 4946 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.073 |
Detector resolution: 0 pixels mm-1 | θmax = 66.0°, θmin = 4.7° |
ωκ scans | h = −11→5 |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | k = −16→16 |
Tmin = 0.456, Tmax = 1.000 | l = −21→21 |
23976 measured reflections | |
Refinement top
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)] = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.218 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.004 |
7818 reflections | Δρmax = 0.71 e Å−3 |
677 parameters | Δρmin = −0.34 e Å−3 |
15 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0009 (2) |
Crystal data top
C6H6O7·2(C17H19FN3O3)·C4H8O·3(H2O) | γ = 68.03 (5)° |
Mr = 980.96 | V = 2321.9 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.225 (2) Å | Cu Kα radiation |
b = 13.8350 (6) Å | µ = 0.96 mm−1 |
c = 18.560 (7) Å | T = 293 K |
α = 72.83 (4)° | 0.64 × 0.43 × 0.07 mm |
β = 86.82 (6)° | |
Data collection top
CCD diffractometer | 7818 independent reflections |
Absorption correction: multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | 4946 reflections with I > 2σ(I) |
Tmin = 0.456, Tmax = 1.000 | Rint = 0.073 |
23976 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.074 | 15 restraints |
wR(F2) = 0.218 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.71 e Å−3 |
7818 reflections | Δρmin = −0.34 e Å−3 |
677 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
F1A | 0.2935 (2) | 0.29579 (19) | 0.44355 (13) | 0.0826 (7) | |
F1B | 1.2509 (2) | 0.16831 (16) | 0.58960 (10) | 0.0648 (5) | |
N1A | 0.7307 (2) | 0.44472 (17) | 0.39827 (14) | 0.0437 (6) | |
N1B | 0.7885 (2) | 0.06533 (17) | 0.56138 (13) | 0.0430 (6) | |
N2A | 0.3597 (3) | 0.3709 (2) | 0.29820 (16) | 0.0579 (7) | |
N2B | 1.1405 (3) | 0.07845 (19) | 0.72053 (13) | 0.0476 (6) | |
N3A | 0.2316 (3) | 0.3096 (2) | 0.19826 (17) | 0.0596 (8) | |
H3AA | 0.200 (4) | 0.259 (3) | 0.197 (3) | 0.091 (13)* | |
H3AB | 0.188 (4) | 0.372 (2) | 0.164 (2) | 0.090 (14)* | |
N3B | 1.2875 (3) | 0.0213 (2) | 0.86166 (16) | 0.0544 (7) | |
H3BA | 1.370 (3) | −0.015 (3) | 0.887 (2) | 0.073 (11)* | |
H3BB | 1.228 (4) | 0.068 (3) | 0.882 (2) | 0.087 (14)* | |
O1A | 0.9673 (3) | 0.4222 (3) | 0.58144 (17) | 0.0962 (10) | |
O1B | 0.6170 (2) | 0.11912 (18) | 0.34922 (13) | 0.0654 (7) | |
O2A | 0.8328 (3) | 0.3579 (2) | 0.66253 (15) | 0.0762 (8) | |
H2AA | 0.761 (4) | 0.345 (4) | 0.658 (3) | 0.12 (2)* | |
O2B | 0.7685 (3) | 0.19279 (18) | 0.29148 (13) | 0.0590 (6) | |
H2BA | 0.826 (4) | 0.211 (3) | 0.308 (2) | 0.089 (14)* | |
O3A | 0.6245 (2) | 0.33028 (18) | 0.61512 (13) | 0.0602 (6) | |
O3B | 0.9494 (2) | 0.21080 (16) | 0.37021 (12) | 0.0532 (5) | |
O4 | 1.4400 (3) | 0.12180 (19) | 1.08156 (15) | 0.0734 (8) | |
O5 | 1.3799 (2) | 0.07063 (18) | 0.99019 (14) | 0.0659 (7) | |
H5A | 1.5000 | 0.0000 | 1.0000 | 0.14 (3)* | |
O6 | 1.0423 (3) | 0.44141 (19) | 0.87245 (16) | 0.0786 (8) | |
O7 | 0.8456 (3) | 0.51603 (19) | 0.92689 (16) | 0.0796 (8) | |
O8 | 1.1327 (2) | 0.22795 (17) | 0.89539 (11) | 0.0523 (5) | |
H8A | 1.116 (4) | 0.2937 (17) | 0.875 (2) | 0.090 (14)* | |
O9 | 1.0600 (3) | 0.09705 (17) | 1.07993 (13) | 0.0628 (6) | |
O10 | 1.0511 (2) | 0.07025 (16) | 0.96819 (12) | 0.0569 (6) | |
H10E | 1.0000 | 0.0000 | 1.0000 | 0.092 (18)* | |
O11 | 0.6303 (7) | 0.3351 (5) | 0.8892 (3) | 0.185 (2) | |
O12 | 1.0786 (4) | 0.1784 (3) | 1.19615 (16) | 0.0768 (8) | |
H12E | 1.008 (3) | 0.235 (2) | 1.184 (3) | 0.086 (17)* | |
H12F | 1.064 (4) | 0.154 (3) | 1.1612 (17) | 0.070 (11)* | |
O13 | 1.1398 (4) | 0.6144 (3) | 0.8325 (2) | 0.0975 (10) | |
H13A | 1.121 (5) | 0.558 (3) | 0.849 (3) | 0.117* | |
H13B | 1.204 (4) | 0.594 (4) | 0.855 (3) | 0.117* | |
O14A | 1.3839 (12) | 0.5178 (12) | 1.0379 (8) | 0.079 (6) | 0.187 (8) |
H14E | 1.3797 | 0.5624 | 1.0620 | 0.094* | 0.187 (8) |
H14F | 1.3072 | 0.5025 | 1.0532 | 0.094* | 0.187 (8) |
O14B | 1.3545 (8) | 0.5264 (7) | 0.9477 (6) | 0.289 (7) | 0.813 (8) |
H14G | 1.4388 | 0.5131 | 0.9550 | 0.347* | 0.813 (8) |
H14H | 1.2863 | 0.5457 | 0.9675 | 0.347* | 0.813 (8) |
C1A | 0.8051 (3) | 0.4380 (2) | 0.45839 (18) | 0.0475 (7) | |
H1AA | 0.8805 | 0.4612 | 0.4498 | 0.057* | |
C1B | 0.7356 (3) | 0.0837 (2) | 0.49177 (17) | 0.0435 (7) | |
H1BA | 0.6610 | 0.0622 | 0.4877 | 0.052* | |
C2A | 0.7753 (3) | 0.3988 (2) | 0.53164 (18) | 0.0472 (7) | |
C2B | 0.7850 (3) | 0.1322 (2) | 0.42611 (16) | 0.0406 (6) | |
C3A | 0.6591 (3) | 0.3645 (2) | 0.54775 (18) | 0.0457 (7) | |
C3B | 0.8996 (3) | 0.1655 (2) | 0.42926 (16) | 0.0405 (6) | |
C4A | 0.5809 (3) | 0.3699 (2) | 0.48286 (17) | 0.0428 (7) | |
C4B | 0.9585 (3) | 0.14477 (19) | 0.50387 (15) | 0.0379 (6) | |
C5A | 0.4664 (3) | 0.3346 (2) | 0.49266 (18) | 0.0502 (7) | |
H5AA | 0.4388 | 0.3098 | 0.5410 | 0.060* | |
C5B | 1.0750 (3) | 0.1709 (2) | 0.51371 (16) | 0.0427 (7) | |
H5BA | 1.1138 | 0.2037 | 0.4716 | 0.051* | |
C6A | 0.3968 (3) | 0.3368 (2) | 0.43196 (19) | 0.0533 (8) | |
C6B | 1.1318 (3) | 0.1493 (2) | 0.58355 (17) | 0.0444 (7) | |
C7A | 0.4315 (3) | 0.3755 (2) | 0.35738 (18) | 0.0470 (7) | |
C7B | 1.0756 (3) | 0.1021 (2) | 0.65111 (16) | 0.0410 (6) | |
C8A | 0.5444 (3) | 0.4100 (2) | 0.34766 (18) | 0.0460 (7) | |
H8AA | 0.5712 | 0.4346 | 0.2991 | 0.055* | |
C8B | 0.9611 (3) | 0.0754 (2) | 0.64118 (16) | 0.0415 (6) | |
H8BA | 0.9215 | 0.0436 | 0.6834 | 0.050* | |
C9A | 0.6183 (3) | 0.4085 (2) | 0.40906 (17) | 0.0422 (6) | |
C9B | 0.9036 (3) | 0.0952 (2) | 0.56908 (16) | 0.0392 (6) | |
C10A | 0.7700 (3) | 0.4849 (2) | 0.32148 (18) | 0.0517 (7) | |
H10A | 0.8131 | 0.4299 | 0.2950 | 0.062* | |
C10B | 0.7378 (3) | 0.0050 (2) | 0.62822 (18) | 0.0506 (7) | |
H10B | 0.8020 | −0.0703 | 0.6519 | 0.061* | |
C11A | 0.6768 (4) | 0.5942 (3) | 0.2739 (2) | 0.0647 (9) | |
H11A | 0.5955 | 0.6356 | 0.2965 | 0.078* | |
H11B | 0.6627 | 0.6042 | 0.2206 | 0.078* | |
C11B | 0.6520 (4) | 0.0627 (3) | 0.6810 (2) | 0.0671 (9) | |
H11C | 0.6296 | 0.1405 | 0.6688 | 0.081* | |
H11D | 0.6660 | 0.0237 | 0.7345 | 0.081* | |
C12A | 0.8205 (4) | 0.5765 (3) | 0.3027 (2) | 0.0665 (9) | |
H12A | 0.8931 | 0.5758 | 0.2667 | 0.080* | |
H12B | 0.8260 | 0.6072 | 0.3426 | 0.080* | |
C12B | 0.5861 (4) | 0.0239 (3) | 0.6308 (2) | 0.0693 (10) | |
H12C | 0.5601 | −0.0384 | 0.6540 | 0.083* | |
H12D | 0.5237 | 0.0784 | 0.5884 | 0.083* | |
C13A | 0.8675 (4) | 0.3949 (3) | 0.5924 (2) | 0.0619 (9) | |
C13B | 0.7158 (3) | 0.1463 (2) | 0.35353 (18) | 0.0492 (7) | |
C14A | 0.2069 (3) | 0.4091 (3) | 0.2907 (2) | 0.0587 (8) | |
H14A | 0.1697 | 0.4794 | 0.2524 | 0.070* | |
H14B | 0.1677 | 0.4179 | 0.3383 | 0.070* | |
C14B | 1.1845 (4) | 0.1575 (2) | 0.74016 (18) | 0.0544 (8) | |
H14C | 1.1094 | 0.2015 | 0.7646 | 0.065* | |
H14D | 1.2035 | 0.2057 | 0.6947 | 0.065* | |
C15A | 0.1650 (4) | 0.3275 (3) | 0.2689 (2) | 0.0613 (9) | |
H15A | 0.1954 | 0.2590 | 0.3091 | 0.074* | |
H15B | 0.0631 | 0.3544 | 0.2612 | 0.074* | |
C15B | 1.3150 (4) | 0.0976 (3) | 0.79233 (19) | 0.0590 (8) | |
H15C | 1.3914 | 0.0568 | 0.7668 | 0.071* | |
H15D | 1.3434 | 0.1495 | 0.8063 | 0.071* | |
C16A | 0.3863 (4) | 0.2795 (3) | 0.2024 (2) | 0.0608 (9) | |
H16A | 0.4222 | 0.2763 | 0.1533 | 0.073* | |
H16B | 0.4306 | 0.2078 | 0.2384 | 0.073* | |
C16B | 1.2319 (3) | −0.0543 (2) | 0.84268 (18) | 0.0542 (8) | |
H16C | 1.2061 | −0.0974 | 0.8885 | 0.065* | |
H16D | 1.3052 | −0.1039 | 0.8209 | 0.065* | |
C17A | 0.4233 (4) | 0.3624 (3) | 0.2266 (2) | 0.0611 (9) | |
H17A | 0.5250 | 0.3393 | 0.2328 | 0.073* | |
H17B | 0.3873 | 0.4328 | 0.1883 | 0.073* | |
C17B | 1.1042 (3) | 0.0085 (2) | 0.78732 (17) | 0.0499 (7) | |
H17C | 1.0735 | −0.0420 | 0.7730 | 0.060* | |
H17D | 1.0272 | 0.0525 | 0.8108 | 0.060* | |
C18 | 1.3567 (3) | 0.1346 (2) | 1.03121 (18) | 0.0495 (7) | |
C19 | 1.2186 (3) | 0.2321 (2) | 1.01449 (17) | 0.0470 (7) | |
H19A | 1.2380 | 0.2955 | 0.9852 | 0.056* | |
H19B | 1.1849 | 0.2444 | 1.0621 | 0.056* | |
C20 | 1.0987 (3) | 0.2264 (2) | 0.97223 (15) | 0.0432 (7) | |
C21 | 0.9608 (3) | 0.3238 (2) | 0.97133 (18) | 0.0514 (7) | |
H21A | 0.8830 | 0.3081 | 0.9566 | 0.062* | |
H21B | 0.9475 | 0.3284 | 1.0225 | 0.062* | |
C22 | 0.9502 (4) | 0.4345 (3) | 0.9204 (2) | 0.0630 (10) | |
C23 | 1.0703 (3) | 0.1230 (2) | 1.01075 (17) | 0.0442 (7) | |
C24 | 0.6974 (8) | 0.3194 (5) | 0.8251 (3) | 0.122 (2) | |
H24A | 0.7884 | 0.3260 | 0.8257 | 0.147* | |
H24B | 0.6410 | 0.3736 | 0.7806 | 0.147* | |
C25 | 0.7154 (9) | 0.2124 (5) | 0.8240 (5) | 0.156 (3) | |
H25A | 0.6824 | 0.2150 | 0.7752 | 0.188* | |
H25B | 0.8144 | 0.1650 | 0.8332 | 0.188* | |
C26 | 0.6349 (12) | 0.1726 (6) | 0.8820 (7) | 0.205 (5) | |
H26A | 0.5445 | 0.1817 | 0.8613 | 0.246* | |
H26B | 0.6855 | 0.0959 | 0.9081 | 0.246* | |
C27 | 0.6166 (14) | 0.2366 (11) | 0.9308 (5) | 0.233 (6) | |
H27A | 0.6874 | 0.1984 | 0.9727 | 0.279* | |
H27B | 0.5240 | 0.2512 | 0.9510 | 0.279* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.0958 (16) | 0.1116 (16) | 0.0677 (14) | −0.0759 (13) | −0.0034 (11) | −0.0159 (12) |
F1B | 0.0691 (12) | 0.0948 (13) | 0.0470 (11) | −0.0530 (10) | −0.0092 (9) | −0.0134 (10) |
N1A | 0.0546 (14) | 0.0462 (13) | 0.0385 (14) | −0.0245 (10) | −0.0037 (10) | −0.0161 (11) |
N1B | 0.0513 (13) | 0.0473 (12) | 0.0378 (13) | −0.0263 (10) | −0.0065 (10) | −0.0111 (10) |
N2A | 0.0552 (15) | 0.0769 (17) | 0.0558 (17) | −0.0269 (13) | −0.0070 (12) | −0.0353 (14) |
N2B | 0.0681 (16) | 0.0565 (14) | 0.0308 (13) | −0.0357 (12) | −0.0081 (11) | −0.0129 (11) |
N3A | 0.087 (2) | 0.0504 (16) | 0.0509 (17) | −0.0341 (15) | −0.0169 (15) | −0.0146 (14) |
N3B | 0.0567 (17) | 0.0678 (17) | 0.0440 (16) | −0.0202 (14) | −0.0109 (13) | −0.0258 (14) |
O1A | 0.111 (2) | 0.143 (3) | 0.0682 (19) | −0.087 (2) | −0.0164 (16) | −0.0246 (18) |
O1B | 0.0748 (15) | 0.0750 (15) | 0.0561 (15) | −0.0384 (12) | −0.0208 (12) | −0.0154 (12) |
O2A | 0.098 (2) | 0.0944 (18) | 0.0490 (16) | −0.0462 (16) | −0.0129 (14) | −0.0229 (14) |
O2B | 0.0734 (15) | 0.0702 (14) | 0.0376 (13) | −0.0308 (12) | −0.0116 (11) | −0.0142 (11) |
O3A | 0.0777 (15) | 0.0682 (14) | 0.0392 (13) | −0.0314 (11) | −0.0006 (11) | −0.0165 (11) |
O3B | 0.0673 (14) | 0.0622 (12) | 0.0345 (12) | −0.0320 (10) | −0.0037 (10) | −0.0090 (10) |
O4 | 0.0756 (16) | 0.0805 (15) | 0.0660 (17) | −0.0177 (12) | −0.0291 (13) | −0.0337 (13) |
O5 | 0.0642 (14) | 0.0673 (14) | 0.0683 (16) | −0.0090 (11) | −0.0211 (12) | −0.0389 (12) |
O6 | 0.113 (2) | 0.0563 (14) | 0.0578 (17) | −0.0308 (14) | 0.0063 (15) | −0.0058 (12) |
O7 | 0.0927 (19) | 0.0532 (14) | 0.0717 (19) | −0.0055 (13) | −0.0160 (14) | −0.0130 (13) |
O8 | 0.0798 (15) | 0.0509 (13) | 0.0305 (12) | −0.0274 (10) | 0.0008 (10) | −0.0138 (10) |
O9 | 0.1074 (19) | 0.0606 (13) | 0.0391 (13) | −0.0503 (12) | 0.0051 (12) | −0.0171 (10) |
O10 | 0.0869 (16) | 0.0574 (12) | 0.0463 (13) | −0.0414 (11) | −0.0004 (11) | −0.0242 (10) |
O11 | 0.288 (7) | 0.205 (5) | 0.135 (5) | −0.151 (5) | 0.089 (5) | −0.092 (4) |
O12 | 0.116 (3) | 0.093 (2) | 0.0544 (17) | −0.066 (2) | 0.0045 (16) | −0.0337 (16) |
O13 | 0.131 (3) | 0.099 (2) | 0.079 (2) | −0.059 (2) | −0.0012 (19) | −0.0267 (19) |
O14A | 0.038 (7) | 0.126 (12) | 0.054 (9) | −0.004 (6) | 0.007 (5) | −0.036 (8) |
O14B | 0.143 (6) | 0.308 (10) | 0.402 (16) | −0.008 (6) | −0.129 (8) | −0.159 (10) |
C1A | 0.0560 (17) | 0.0476 (15) | 0.0474 (18) | −0.0250 (13) | −0.0077 (14) | −0.0173 (13) |
C1B | 0.0468 (15) | 0.0438 (14) | 0.0462 (17) | −0.0195 (11) | −0.0089 (13) | −0.0168 (13) |
C2A | 0.0625 (18) | 0.0442 (15) | 0.0416 (17) | −0.0219 (13) | −0.0101 (13) | −0.0173 (13) |
C2B | 0.0489 (15) | 0.0397 (14) | 0.0354 (16) | −0.0161 (11) | −0.0069 (12) | −0.0133 (12) |
C3A | 0.0574 (17) | 0.0396 (14) | 0.0410 (17) | −0.0147 (12) | −0.0044 (13) | −0.0165 (13) |
C3B | 0.0517 (16) | 0.0371 (14) | 0.0333 (15) | −0.0156 (11) | −0.0054 (12) | −0.0114 (12) |
C4A | 0.0542 (16) | 0.0411 (14) | 0.0382 (16) | −0.0189 (12) | −0.0040 (12) | −0.0164 (12) |
C4B | 0.0463 (15) | 0.0375 (13) | 0.0352 (15) | −0.0172 (11) | −0.0022 (11) | −0.0154 (11) |
C5A | 0.0602 (18) | 0.0524 (17) | 0.0461 (18) | −0.0286 (14) | 0.0010 (14) | −0.0162 (14) |
C5B | 0.0535 (16) | 0.0486 (15) | 0.0315 (15) | −0.0250 (12) | −0.0054 (12) | −0.0104 (12) |
C6A | 0.0592 (18) | 0.0581 (17) | 0.055 (2) | −0.0343 (14) | −0.0034 (15) | −0.0177 (15) |
C6B | 0.0489 (16) | 0.0531 (16) | 0.0410 (16) | −0.0274 (12) | −0.0002 (12) | −0.0167 (13) |
C7A | 0.0572 (17) | 0.0465 (15) | 0.0446 (18) | −0.0218 (13) | −0.0057 (13) | −0.0192 (13) |
C7B | 0.0534 (16) | 0.0444 (14) | 0.0304 (15) | −0.0218 (12) | −0.0039 (12) | −0.0126 (12) |
C8A | 0.0576 (17) | 0.0475 (15) | 0.0417 (17) | −0.0231 (13) | −0.0065 (13) | −0.0196 (13) |
C8B | 0.0495 (16) | 0.0474 (15) | 0.0340 (15) | −0.0227 (12) | −0.0026 (12) | −0.0142 (12) |
C9A | 0.0523 (16) | 0.0380 (14) | 0.0415 (17) | −0.0186 (12) | −0.0029 (12) | −0.0160 (12) |
C9B | 0.0439 (15) | 0.0381 (13) | 0.0388 (16) | −0.0164 (11) | −0.0047 (11) | −0.0133 (12) |
C10A | 0.0612 (19) | 0.0587 (18) | 0.0430 (18) | −0.0306 (14) | 0.0017 (14) | −0.0155 (14) |
C10B | 0.0588 (18) | 0.0545 (17) | 0.0438 (18) | −0.0301 (14) | −0.0013 (14) | −0.0101 (14) |
C11A | 0.073 (2) | 0.068 (2) | 0.049 (2) | −0.0302 (17) | −0.0076 (16) | −0.0047 (16) |
C11B | 0.074 (2) | 0.080 (2) | 0.057 (2) | −0.0388 (18) | 0.0107 (17) | −0.0228 (18) |
C12A | 0.082 (2) | 0.070 (2) | 0.054 (2) | −0.0438 (18) | −0.0076 (17) | −0.0050 (17) |
C12B | 0.064 (2) | 0.085 (2) | 0.063 (2) | −0.0430 (18) | −0.0041 (17) | −0.0081 (19) |
C13A | 0.083 (2) | 0.065 (2) | 0.047 (2) | −0.0348 (18) | −0.0123 (17) | −0.0189 (17) |
C13B | 0.0604 (18) | 0.0457 (15) | 0.0439 (18) | −0.0185 (13) | −0.0139 (14) | −0.0153 (14) |
C14A | 0.0601 (19) | 0.0661 (19) | 0.061 (2) | −0.0271 (15) | −0.0085 (16) | −0.0276 (17) |
C14B | 0.077 (2) | 0.0557 (17) | 0.0424 (18) | −0.0347 (15) | −0.0070 (15) | −0.0177 (14) |
C15A | 0.075 (2) | 0.069 (2) | 0.053 (2) | −0.0391 (17) | −0.0058 (17) | −0.0210 (17) |
C15B | 0.070 (2) | 0.077 (2) | 0.049 (2) | −0.0416 (17) | −0.0029 (15) | −0.0260 (17) |
C16A | 0.071 (2) | 0.0612 (19) | 0.048 (2) | −0.0163 (15) | −0.0152 (16) | −0.0207 (16) |
C16B | 0.066 (2) | 0.0612 (18) | 0.0389 (17) | −0.0267 (15) | −0.0070 (14) | −0.0148 (14) |
C17A | 0.067 (2) | 0.073 (2) | 0.050 (2) | −0.0270 (16) | −0.0057 (16) | −0.0250 (17) |
C17B | 0.0626 (18) | 0.0608 (17) | 0.0340 (16) | −0.0320 (14) | −0.0069 (13) | −0.0116 (14) |
C18 | 0.0574 (18) | 0.0509 (16) | 0.0476 (18) | −0.0265 (13) | −0.0061 (14) | −0.0157 (14) |
C19 | 0.0615 (18) | 0.0478 (15) | 0.0411 (17) | −0.0269 (13) | −0.0076 (13) | −0.0164 (13) |
C20 | 0.0619 (17) | 0.0448 (15) | 0.0290 (15) | −0.0232 (12) | −0.0038 (12) | −0.0144 (12) |
C21 | 0.0610 (19) | 0.0489 (16) | 0.0450 (18) | −0.0198 (13) | −0.0045 (14) | −0.0145 (14) |
C22 | 0.084 (3) | 0.0527 (19) | 0.049 (2) | −0.0205 (18) | −0.0233 (18) | −0.0117 (16) |
C23 | 0.0559 (17) | 0.0462 (15) | 0.0378 (17) | −0.0232 (12) | −0.0051 (12) | −0.0163 (13) |
C24 | 0.178 (6) | 0.145 (5) | 0.077 (4) | −0.101 (5) | 0.009 (4) | −0.028 (3) |
C25 | 0.192 (8) | 0.100 (5) | 0.147 (7) | −0.035 (4) | 0.021 (6) | −0.023 (4) |
C26 | 0.258 (11) | 0.110 (5) | 0.227 (12) | −0.095 (6) | −0.018 (9) | 0.017 (6) |
C27 | 0.349 (15) | 0.336 (15) | 0.101 (6) | −0.261 (14) | 0.075 (8) | −0.029 (8) |
Geometric parameters (Å, º) top
F1A—C6A | 1.355 (4) | C5B—C6B | 1.353 (4) |
F1B—C6B | 1.355 (3) | C5B—H5BA | 0.9300 |
N1A—C1A | 1.346 (3) | C6A—C7A | 1.407 (5) |
N1A—C9A | 1.399 (4) | C6B—C7B | 1.431 (4) |
N1A—C10A | 1.462 (4) | C7A—C8A | 1.390 (4) |
N1B—C1B | 1.345 (4) | C7B—C8B | 1.389 (4) |
N1B—C9B | 1.412 (3) | C8A—C9A | 1.393 (4) |
N1B—C10B | 1.465 (4) | C8A—H8AA | 0.9300 |
N2A—C7A | 1.384 (4) | C8B—C9B | 1.400 (4) |
N2A—C14A | 1.450 (4) | C8B—H8BA | 0.9300 |
N2A—C17A | 1.464 (5) | C10A—C11A | 1.484 (5) |
N2B—C7B | 1.375 (3) | C10A—C12A | 1.484 (4) |
N2B—C17B | 1.456 (4) | C10A—H10A | 0.9800 |
N2B—C14B | 1.467 (3) | C10B—C12B | 1.474 (5) |
N3A—C16A | 1.478 (5) | C10B—C11B | 1.486 (5) |
N3A—C15A | 1.485 (5) | C10B—H10B | 0.9800 |
N3A—H3AA | 0.878 (19) | C11A—C12A | 1.498 (5) |
N3A—H3AB | 0.879 (19) | C11A—H11A | 0.9700 |
N3B—C16B | 1.492 (4) | C11A—H11B | 0.9700 |
N3B—C15B | 1.493 (5) | C11B—C12B | 1.498 (5) |
N3B—H3BA | 0.879 (19) | C11B—H11C | 0.9700 |
N3B—H3BB | 0.870 (19) | C11B—H11D | 0.9700 |
O1A—C13A | 1.202 (5) | C12A—H12A | 0.9700 |
O1B—C13B | 1.216 (4) | C12A—H12B | 0.9700 |
O2A—C13A | 1.331 (5) | C12B—H12C | 0.9700 |
O2A—H2AA | 0.84 (2) | C12B—H12D | 0.9700 |
O2B—C13B | 1.335 (4) | C14A—C15A | 1.508 (4) |
O2B—H2BA | 0.825 (19) | C14A—H14A | 0.9700 |
O3A—C3A | 1.281 (4) | C14A—H14B | 0.9700 |
O3B—C3B | 1.274 (4) | C14B—C15B | 1.499 (4) |
O4—C18 | 1.228 (3) | C14B—H14C | 0.9700 |
O5—C18 | 1.281 (4) | C14B—H14D | 0.9700 |
O5—H5A | 1.232 (2) | C15A—H15A | 0.9700 |
O6—C22 | 1.269 (5) | C15A—H15B | 0.9700 |
O7—C22 | 1.263 (4) | C15B—H15C | 0.9700 |
O8—C20 | 1.445 (3) | C15B—H15D | 0.9700 |
O8—H8A | 0.829 (19) | C16A—C17A | 1.519 (4) |
O9—C23 | 1.237 (4) | C16A—H16A | 0.9700 |
O10—C23 | 1.288 (3) | C16A—H16B | 0.9700 |
O10—H10E | 1.254 (2) | C16B—C17B | 1.513 (4) |
O11—C24 | 1.372 (7) | C16B—H16C | 0.9700 |
O11—C27 | 1.408 (10) | C16B—H16D | 0.9700 |
O12—H12E | 0.825 (19) | C17A—H17A | 0.9700 |
O12—H12F | 0.853 (19) | C17A—H17B | 0.9700 |
O13—H13A | 0.839 (19) | C17B—H17C | 0.9700 |
O13—H13B | 0.72 (2) | C17B—H17D | 0.9700 |
O14A—H14E | 0.8509 | C18—C19 | 1.511 (4) |
O14A—H14F | 0.8973 | C19—C20 | 1.530 (4) |
O14B—H14G | 0.8207 | C19—H19A | 0.9700 |
O14B—H14H | 0.7645 | C19—H19B | 0.9700 |
C1A—C2A | 1.370 (5) | C20—C23 | 1.525 (4) |
C1A—H1AA | 0.9300 | C20—C21 | 1.540 (4) |
C1B—C2B | 1.376 (4) | C21—C22 | 1.511 (5) |
C1B—H1BA | 0.9300 | C21—H21A | 0.9700 |
C2A—C3A | 1.423 (4) | C21—H21B | 0.9700 |
C2A—C13A | 1.486 (4) | C24—C25 | 1.428 (8) |
C2B—C3B | 1.421 (4) | C24—H24A | 0.9700 |
C2B—C13B | 1.483 (4) | C24—H24B | 0.9700 |
C3A—C4A | 1.451 (4) | C25—C26 | 1.425 (12) |
C3B—C4B | 1.446 (4) | C25—H25A | 0.9700 |
C4A—C9A | 1.404 (4) | C25—H25B | 0.9700 |
C4A—C5A | 1.411 (4) | C26—C27 | 1.404 (12) |
C4B—C5B | 1.404 (4) | C26—H26A | 0.9700 |
C4B—C9B | 1.404 (4) | C26—H26B | 0.9700 |
C5A—C6A | 1.353 (4) | C27—H27A | 0.9700 |
C5A—H5AA | 0.9300 | C27—H27B | 0.9700 |
| | | |
C1A—N1A—C9A | 120.0 (3) | C10A—C12A—H12B | 117.8 |
C1A—N1A—C10A | 120.7 (2) | C11A—C12A—H12B | 117.8 |
C9A—N1A—C10A | 119.3 (2) | H12A—C12A—H12B | 114.9 |
C1B—N1B—C9B | 119.1 (3) | C10B—C12B—C11B | 60.0 (2) |
C1B—N1B—C10B | 120.6 (2) | C10B—C12B—H12C | 117.8 |
C9B—N1B—C10B | 119.9 (2) | C11B—C12B—H12C | 117.8 |
C7A—N2A—C14A | 122.9 (3) | C10B—C12B—H12D | 117.8 |
C7A—N2A—C17A | 122.3 (3) | C11B—C12B—H12D | 117.8 |
C14A—N2A—C17A | 111.8 (3) | H12C—C12B—H12D | 114.9 |
C7B—N2B—C17B | 120.1 (2) | O1A—C13A—O2A | 120.5 (3) |
C7B—N2B—C14B | 121.5 (2) | O1A—C13A—C2A | 124.3 (3) |
C17B—N2B—C14B | 111.1 (2) | O2A—C13A—C2A | 115.2 (3) |
C16A—N3A—C15A | 113.3 (3) | O1B—C13B—O2B | 121.0 (3) |
C16A—N3A—H3AA | 118 (3) | O1B—C13B—C2B | 123.6 (3) |
C15A—N3A—H3AA | 96 (3) | O2B—C13B—C2B | 115.4 (3) |
C16A—N3A—H3AB | 112 (3) | N2A—C14A—C15A | 109.4 (3) |
C15A—N3A—H3AB | 104 (3) | N2A—C14A—H14A | 109.8 |
H3AA—N3A—H3AB | 112 (4) | C15A—C14A—H14A | 109.8 |
C16B—N3B—C15B | 111.7 (2) | N2A—C14A—H14B | 109.8 |
C16B—N3B—H3BA | 111 (2) | C15A—C14A—H14B | 109.8 |
C15B—N3B—H3BA | 104 (3) | H14A—C14A—H14B | 108.2 |
C16B—N3B—H3BB | 115 (3) | N2B—C14B—C15B | 109.3 (2) |
C15B—N3B—H3BB | 100 (3) | N2B—C14B—H14C | 109.8 |
H3BA—N3B—H3BB | 113 (4) | C15B—C14B—H14C | 109.8 |
C13A—O2A—H2AA | 105 (4) | N2B—C14B—H14D | 109.8 |
C13B—O2B—H2BA | 104 (3) | C15B—C14B—H14D | 109.8 |
C18—O5—H5A | 114.2 (2) | H14C—C14B—H14D | 108.3 |
C20—O8—H8A | 101 (3) | N3A—C15A—C14A | 109.7 (3) |
C23—O10—H10E | 114.7 (2) | N3A—C15A—H15A | 109.7 |
C24—O11—C27 | 107.8 (6) | C14A—C15A—H15A | 109.7 |
H12E—O12—H12F | 95 (4) | N3A—C15A—H15B | 109.7 |
H13A—O13—H13B | 96 (6) | C14A—C15A—H15B | 109.7 |
H14E—O14A—H14F | 100.8 | H15A—C15A—H15B | 108.2 |
H14G—O14B—H14H | 137.5 | N3B—C15B—C14B | 110.1 (3) |
N1A—C1A—C2A | 123.4 (3) | N3B—C15B—H15C | 109.6 |
N1A—C1A—H1AA | 118.3 | C14B—C15B—H15C | 109.6 |
C2A—C1A—H1AA | 118.3 | N3B—C15B—H15D | 109.6 |
N1B—C1B—C2B | 124.1 (2) | C14B—C15B—H15D | 109.6 |
N1B—C1B—H1BA | 118.0 | H15C—C15B—H15D | 108.2 |
C2B—C1B—H1BA | 118.0 | N3A—C16A—C17A | 110.5 (3) |
C1A—C2A—C3A | 120.4 (3) | N3A—C16A—H16A | 109.5 |
C1A—C2A—C13A | 117.5 (3) | C17A—C16A—H16A | 109.5 |
C3A—C2A—C13A | 122.0 (3) | N3A—C16A—H16B | 109.5 |
C1B—C2B—C3B | 120.1 (2) | C17A—C16A—H16B | 109.5 |
C1B—C2B—C13B | 117.7 (3) | H16A—C16A—H16B | 108.1 |
C3B—C2B—C13B | 122.2 (3) | N3B—C16B—C17B | 110.9 (2) |
O3A—C3A—C2A | 122.8 (3) | N3B—C16B—H16C | 109.4 |
O3A—C3A—C4A | 121.1 (3) | C17B—C16B—H16C | 109.4 |
C2A—C3A—C4A | 116.0 (3) | N3B—C16B—H16D | 109.5 |
O3B—C3B—C2B | 122.6 (2) | C17B—C16B—H16D | 109.4 |
O3B—C3B—C4B | 121.2 (2) | H16C—C16B—H16D | 108.0 |
C2B—C3B—C4B | 116.2 (3) | N2A—C17A—C16A | 108.4 (3) |
C9A—C4A—C5A | 118.4 (3) | N2A—C17A—H17A | 110.0 |
C9A—C4A—C3A | 121.0 (3) | C16A—C17A—H17A | 110.0 |
C5A—C4A—C3A | 120.6 (3) | N2A—C17A—H17B | 110.0 |
C5B—C4B—C9B | 117.5 (2) | C16A—C17A—H17B | 110.0 |
C5B—C4B—C3B | 121.1 (3) | H17A—C17A—H17B | 108.4 |
C9B—C4B—C3B | 121.3 (2) | N2B—C17B—C16B | 109.5 (3) |
C6A—C5A—C4A | 120.2 (3) | N2B—C17B—H17C | 109.8 |
C6A—C5A—H5AA | 119.9 | C16B—C17B—H17C | 109.8 |
C4A—C5A—H5AA | 119.9 | N2B—C17B—H17D | 109.8 |
C6B—C5B—C4B | 121.0 (3) | C16B—C17B—H17D | 109.8 |
C6B—C5B—H5BA | 119.5 | H17C—C17B—H17D | 108.2 |
C4B—C5B—H5BA | 119.5 | O4—C18—O5 | 123.9 (3) |
C5A—C6A—F1A | 118.7 (3) | O4—C18—C19 | 119.3 (3) |
C5A—C6A—C7A | 122.6 (3) | O5—C18—C19 | 116.8 (2) |
F1A—C6A—C7A | 118.6 (3) | C18—C19—C20 | 117.5 (2) |
C5B—C6B—F1B | 118.6 (3) | C18—C19—H19A | 107.9 |
C5B—C6B—C7B | 122.8 (3) | C20—C19—H19A | 107.9 |
F1B—C6B—C7B | 118.6 (2) | C18—C19—H19B | 107.9 |
N2A—C7A—C8A | 123.2 (3) | C20—C19—H19B | 107.9 |
N2A—C7A—C6A | 119.5 (3) | H19A—C19—H19B | 107.2 |
C8A—C7A—C6A | 117.2 (3) | O8—C20—C23 | 108.4 (2) |
N2B—C7B—C8B | 123.5 (3) | O8—C20—C19 | 110.7 (3) |
N2B—C7B—C6B | 120.3 (2) | C23—C20—C19 | 111.4 (2) |
C8B—C7B—C6B | 116.0 (2) | O8—C20—C21 | 109.1 (2) |
C7A—C8A—C9A | 121.4 (3) | C23—C20—C21 | 107.0 (2) |
C7A—C8A—H8AA | 119.3 | C19—C20—C21 | 110.1 (2) |
C9A—C8A—H8AA | 119.3 | C22—C21—C20 | 117.1 (3) |
C7B—C8B—C9B | 121.6 (3) | C22—C21—H21A | 108.0 |
C7B—C8B—H8BA | 119.2 | C20—C21—H21A | 108.0 |
C9B—C8B—H8BA | 119.2 | C22—C21—H21B | 108.0 |
C8A—C9A—N1A | 120.8 (3) | C20—C21—H21B | 108.0 |
C8A—C9A—C4A | 120.1 (3) | H21A—C21—H21B | 107.3 |
N1A—C9A—C4A | 119.2 (2) | O7—C22—O6 | 123.3 (3) |
C8B—C9B—C4B | 121.0 (2) | O7—C22—C21 | 117.0 (4) |
C8B—C9B—N1B | 119.8 (3) | O6—C22—C21 | 119.7 (3) |
C4B—C9B—N1B | 119.1 (2) | O9—C23—O10 | 123.5 (3) |
N1A—C10A—C11A | 118.0 (3) | O9—C23—C20 | 119.0 (2) |
N1A—C10A—C12A | 119.5 (3) | O10—C23—C20 | 117.4 (3) |
C11A—C10A—C12A | 60.6 (2) | O11—C24—C25 | 107.4 (6) |
N1A—C10A—H10A | 115.8 | O11—C24—H24A | 110.2 |
C11A—C10A—H10A | 115.8 | C25—C24—H24A | 110.2 |
C12A—C10A—H10A | 115.8 | O11—C24—H24B | 110.2 |
N1B—C10B—C12B | 119.2 (3) | C25—C24—H24B | 110.2 |
N1B—C10B—C11B | 119.9 (3) | H24A—C24—H24B | 108.5 |
C12B—C10B—C11B | 60.8 (2) | C26—C25—C24 | 107.3 (7) |
N1B—C10B—H10B | 115.3 | C26—C25—H25A | 110.3 |
C12B—C10B—H10B | 115.3 | C24—C25—H25A | 110.3 |
C11B—C10B—H10B | 115.3 | C26—C25—H25B | 110.3 |
C10A—C11A—C12A | 59.7 (2) | C24—C25—H25B | 110.3 |
C10A—C11A—H11A | 117.8 | H25A—C25—H25B | 108.5 |
C12A—C11A—H11A | 117.8 | C27—C26—C25 | 104.1 (7) |
C10A—C11A—H11B | 117.8 | C27—C26—H26A | 110.9 |
C12A—C11A—H11B | 117.8 | C25—C26—H26A | 110.9 |
H11A—C11A—H11B | 114.9 | C27—C26—H26B | 110.9 |
C10B—C11B—C12B | 59.2 (2) | C25—C26—H26B | 110.9 |
C10B—C11B—H11C | 117.9 | H26A—C26—H26B | 109.0 |
C12B—C11B—H11C | 117.9 | C26—C27—O11 | 108.0 (7) |
C10B—C11B—H11D | 117.9 | C26—C27—H27A | 110.1 |
C12B—C11B—H11D | 117.9 | O11—C27—H27A | 110.1 |
H11C—C11B—H11D | 115.0 | C26—C27—H27B | 110.1 |
C10A—C12A—C11A | 59.7 (2) | O11—C27—H27B | 110.1 |
C10A—C12A—H12A | 117.8 | H27A—C27—H27B | 108.4 |
C11A—C12A—H12A | 117.8 | | |
Experimental details
| (1) | (2) | (3) | (4) |
Crystal data |
Chemical formula | C17H19FN3O3·C4H3O4·H2O | 2(C17H19FN3O3)·C4H2O4·3(H2O) | C17H19FN3O3·C4H3O4 | C6H6O7·2(C17H19FN3O3)·C4H8O·3(H2O) |
Mr | 465.43 | 832.81 | 447.42 | 980.96 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 9.579 (3), 9.806 (2), 11.612 (4) | 9.922 (4), 30.199 (9), 13.528 (8) | 13.956 (4), 10.459 (4), 15.184 (5) | 10.225 (2), 13.8350 (6), 18.560 (7) |
α, β, γ (°) | 78.66 (2), 89.44 (3), 78.85 (4) | 90, 109.717 (13), 90 | 90, 108.765 (6), 90 | 72.83 (4), 86.82 (6), 68.03 (5) |
V (Å3) | 1048.8 (5) | 3816 (3) | 2098.5 (12) | 2321.9 (10) |
Z | 2 | 4 | 4 | 2 |
Radiation type | Cu Kα | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 1.02 | 0.99 | 0.96 | 0.96 |
Crystal size (mm) | 0.72 × 0.23 × 0.19 | 0.43 × 0.12 × 0.03 | 0.75 × 0.65 × 0.30 | 0.64 × 0.43 × 0.07 |
|
Data collection |
Diffractometer | CCD | CCD | CCD | CCD |
Absorption correction | Multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | Multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | Multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. | Multi-scan Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan. |
Tmin, Tmax | 0.721, 1.000 | 0.676, 0.971 | 0.707, 1.000 | 0.456, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15473, 3866, 3412 | 36407, 7316, 5695 | 20341, 4083, 3531 | 23976, 7818, 4946 |
Rint | 0.055 | 0.125 | 0.047 | 0.073 |
(sin θ/λ)max (Å−1) | 0.609 | 0.618 | 0.618 | 0.593 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.124, 1.04 | 0.082, 0.249, 1.05 | 0.042, 0.123, 1.04 | 0.074, 0.218, 1.13 |
No. of reflections | 3866 | 7316 | 4083 | 7818 |
No. of parameters | 323 | 588 | 311 | 677 |
No. of restraints | 0 | 14 | 2 | 15 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.22 | 0.41, −0.56 | 0.22, −0.19 | 0.71, −0.34 |
Hydrogen-bond geometry (Å, º) for (1) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O6i | 0.933 (19) | 1.968 (19) | 2.8280 (18) | 152.3 (15) |
N3—H3A···O1ii | 0.933 (19) | 2.526 (18) | 3.0244 (18) | 113.7 (13) |
N3—H3B···O4ii | 0.99 (2) | 1.73 (2) | 2.6752 (17) | 160.2 (18) |
O2—H2A···O3 | 0.89 (2) | 1.73 (3) | 2.5708 (17) | 156 (2) |
O7—H7A···O8 | 0.97 (3) | 1.60 (3) | 2.5618 (17) | 172 (2) |
O8—H8B···O5iii | 0.92 (3) | 1.83 (3) | 2.726 (2) | 165 (2) |
O8—H8C···O4iv | 0.91 (3) | 1.93 (3) | 2.833 (2) | 171 (2) |
Symmetry codes: (i) x, y, z+1; (ii) x, y−1, z+1; (iii) x, y−1, z; (iv) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) for (3) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O5i | 0.92 (2) | 2.25 (2) | 2.9770 (18) | 135.7 (18) |
N3—H3A···O4i | 0.92 (2) | 2.30 (2) | 3.0317 (18) | 136.1 (18) |
N3—H3A···O2ii | 0.92 (2) | 2.43 (2) | 3.0911 (17) | 128.4 (18) |
N3—H3B···O7iii | 0.93 (2) | 1.82 (2) | 2.7564 (19) | 175.8 (18) |
O2—H2A···O3 | 0.96 (3) | 1.67 (3) | 2.5521 (17) | 151 (3) |
O4—H4A···O6 | 0.830 (10) | 1.574 (11) | 2.4039 (17) | 179 (5) |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+2, −y+1, −z+1. |