Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015654/om6150sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015654/om6150Isup2.hkl |
CCDC reference: 222907
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.047
- wR factor = 0.125
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.14 Ratio
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C7 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C24 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C25 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 3.05 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 22.00 Perc.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.33 From the CIF: _reflns_number_total 3332 Count of symmetry unique reflns 3400 Completeness (_total/calc) 98.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was synthesized from ethyl (S)-nipecotate L-tartrate (see reaction Scheme). Crystals were grown from an ethyl acetate solution.
Carbon-bound H atoms were placed in idealized positions and refined as a riding model, with C—H = 0.94 Å (0.98 Å for methyl H atoms). Nitrogen-bound H atoms was freely refined. Friedel pairs were merged for the final refinement since no atoms heavier than Si are present and the absolute configuration was known.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
C23H31N2O+·C2F3O2− | Dx = 1.275 Mg m−3 |
Mr = 464.52 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 648 reflections |
a = 10.1973 (7) Å | θ = 3.0–28.7° |
b = 10.8295 (7) Å | µ = 0.10 mm−1 |
c = 21.910 (1) Å | T = 213 K |
V = 2419.6 (3) Å3 | Needle, colorless |
Z = 4 | 0.25 × 0.20 × 0.10 mm |
F(000) = 984 |
Bruker CCD diffractometer | 3113 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 28.3°, θmin = 1.9° |
Detector resolution: 8.3 pixels mm-1 | h = −13→13 |
ω scans | k = −14→9 |
15557 measured reflections | l = −28→26 |
3332 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.52P] where P = (Fo2 + 2Fc2)/3 |
3332 reflections | (Δ/σ)max = 0.001 |
321 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C23H31N2O+·C2F3O2− | V = 2419.6 (3) Å3 |
Mr = 464.52 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.1973 (7) Å | µ = 0.10 mm−1 |
b = 10.8295 (7) Å | T = 213 K |
c = 21.910 (1) Å | 0.25 × 0.20 × 0.10 mm |
Bruker CCD diffractometer | 3113 reflections with I > 2σ(I) |
15557 measured reflections | Rint = 0.055 |
3332 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.40 e Å−3 |
3332 reflections | Δρmin = −0.36 e Å−3 |
321 parameters |
Experimental. Data was collected using a Bruker SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3° per frame for 30 s, such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 Å. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX90 program and refined by least squares method on F2 SHELXL93, incorporated in SHELXTL V5.1. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.77365 (19) | 0.6452 (2) | 0.25998 (9) | 0.0335 (4) | |
H1A | 0.8599 | 0.6417 | 0.2404 | 0.040* | |
H1B | 0.7441 | 0.5604 | 0.2675 | 0.040* | |
O1 | 0.97375 (17) | 0.42215 (18) | 0.32919 (8) | 0.0510 (4) | |
N1 | 0.67772 (16) | 0.71023 (16) | 0.21882 (7) | 0.0311 (3) | |
H1 | 0.602 (3) | 0.704 (2) | 0.2403 (11) | 0.029 (6)* | |
N2 | 0.81872 (16) | 0.52443 (16) | 0.38306 (8) | 0.0334 (4) | |
C2 | 0.78372 (19) | 0.71502 (19) | 0.32052 (9) | 0.0322 (4) | |
H2A | 0.6947 | 0.7199 | 0.3384 | 0.039* | |
C3 | 0.8317 (2) | 0.8468 (2) | 0.30927 (11) | 0.0436 (5) | |
H3A | 0.8347 | 0.8919 | 0.3480 | 0.052* | |
H3B | 0.9206 | 0.8447 | 0.2923 | 0.052* | |
C4 | 0.7400 (3) | 0.9130 (2) | 0.26492 (11) | 0.0449 (5) | |
H4A | 0.6546 | 0.9253 | 0.2845 | 0.054* | |
H4B | 0.7762 | 0.9946 | 0.2553 | 0.054* | |
C5 | 0.7211 (2) | 0.8410 (2) | 0.20607 (10) | 0.0411 (5) | |
H5A | 0.6551 | 0.8824 | 0.1808 | 0.049* | |
H5B | 0.8037 | 0.8396 | 0.1832 | 0.049* | |
C6 | 0.6530 (2) | 0.6370 (2) | 0.16163 (9) | 0.0395 (5) | |
H6A | 0.6490 | 0.5490 | 0.1717 | 0.047* | |
H6B | 0.7257 | 0.6495 | 0.1331 | 0.047* | |
C7 | 0.5250 (3) | 0.6761 (3) | 0.13135 (13) | 0.0581 (7) | |
H7A | 0.4559 | 0.6789 | 0.1624 | 0.070* | |
H7B | 0.5355 | 0.7597 | 0.1150 | 0.070* | |
C8 | 0.4811 (2) | 0.5912 (2) | 0.08004 (10) | 0.0419 (5) | |
C9 | 0.4668 (3) | 0.4647 (3) | 0.08934 (11) | 0.0493 (6) | |
H9A | 0.4886 | 0.4305 | 0.1275 | 0.059* | |
C10 | 0.4211 (3) | 0.3888 (3) | 0.04330 (15) | 0.0631 (8) | |
H10A | 0.4127 | 0.3035 | 0.0503 | 0.076* | |
C11 | 0.3881 (3) | 0.4365 (4) | −0.01218 (14) | 0.0652 (9) | |
H11A | 0.3565 | 0.3845 | −0.0433 | 0.078* | |
C12 | 0.4016 (3) | 0.5629 (4) | −0.02249 (11) | 0.0626 (8) | |
H12A | 0.3790 | 0.5962 | −0.0607 | 0.075* | |
C13 | 0.4479 (2) | 0.6395 (3) | 0.02312 (11) | 0.0516 (6) | |
H13A | 0.4570 | 0.7246 | 0.0157 | 0.062* | |
C14 | 0.8715 (2) | 0.6460 (2) | 0.36570 (10) | 0.0372 (4) | |
H14A | 0.9584 | 0.6348 | 0.3474 | 0.045* | |
H14B | 0.8821 | 0.6963 | 0.4025 | 0.045* | |
C15 | 0.8777 (2) | 0.4190 (2) | 0.36282 (10) | 0.0367 (4) | |
C16 | 0.8188 (2) | 0.2982 (2) | 0.38471 (13) | 0.0468 (5) | |
H16A | 0.8115 | 0.3006 | 0.4293 | 0.056* | |
H16B | 0.7301 | 0.2903 | 0.3680 | 0.056* | |
C17 | 0.8974 (4) | 0.1863 (3) | 0.3667 (2) | 0.0798 (11) | |
H17A | 0.8546 | 0.1125 | 0.3819 | 0.120* | |
H17B | 0.9848 | 0.1922 | 0.3839 | 0.120* | |
H17C | 0.9034 | 0.1821 | 0.3225 | 0.120* | |
C18 | 0.70467 (19) | 0.52458 (19) | 0.42202 (9) | 0.0320 (4) | |
C19 | 0.7195 (2) | 0.5384 (3) | 0.48496 (10) | 0.0453 (5) | |
H19A | 0.8037 | 0.5449 | 0.5021 | 0.054* | |
C20 | 0.6095 (3) | 0.5426 (3) | 0.52228 (11) | 0.0543 (7) | |
H20A | 0.6194 | 0.5510 | 0.5647 | 0.065* | |
C21 | 0.4846 (3) | 0.5345 (3) | 0.49701 (11) | 0.0503 (6) | |
H21A | 0.4102 | 0.5380 | 0.5223 | 0.060* | |
C22 | 0.4704 (2) | 0.5214 (2) | 0.43472 (11) | 0.0427 (5) | |
H22A | 0.3860 | 0.5161 | 0.4177 | 0.051* | |
C23 | 0.5796 (2) | 0.5161 (2) | 0.39692 (9) | 0.0353 (4) | |
H23A | 0.5690 | 0.5068 | 0.3545 | 0.042* | |
C24 | 0.6211 (2) | 0.2773 (2) | 0.22002 (10) | 0.0358 (4) | |
C25 | 0.7464 (3) | 0.2675 (3) | 0.18029 (14) | 0.0545 (7) | |
O2 | 0.6075 (2) | 0.37242 (18) | 0.24934 (10) | 0.0580 (5) | |
O3 | 0.54885 (17) | 0.18503 (18) | 0.21666 (9) | 0.0510 (4) | |
F1A | 0.8041 (6) | 0.1650 (5) | 0.1804 (4) | 0.124 (4) | 0.652 (10) |
F2A | 0.7053 (5) | 0.2798 (5) | 0.11853 (14) | 0.0872 (14) | 0.652 (10) |
F3A | 0.8201 (2) | 0.3675 (2) | 0.17958 (13) | 0.0973 (8) | |
F1B | 0.8463 (5) | 0.2175 (9) | 0.2244 (4) | 0.083 (3) | 0.348 (10) |
F2B | 0.7531 (9) | 0.1915 (18) | 0.1416 (7) | 0.153 (9) | 0.348 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0266 (9) | 0.0381 (10) | 0.0357 (9) | 0.0026 (8) | 0.0002 (7) | 0.0028 (8) |
O1 | 0.0375 (8) | 0.0587 (10) | 0.0567 (9) | 0.0022 (8) | 0.0122 (8) | −0.0017 (9) |
N1 | 0.0254 (7) | 0.0369 (8) | 0.0308 (7) | 0.0013 (7) | 0.0025 (6) | 0.0026 (7) |
N2 | 0.0262 (7) | 0.0364 (8) | 0.0377 (8) | −0.0022 (7) | −0.0009 (7) | 0.0061 (7) |
C2 | 0.0274 (8) | 0.0336 (9) | 0.0355 (9) | −0.0031 (8) | 0.0005 (8) | 0.0027 (8) |
C3 | 0.0412 (11) | 0.0394 (11) | 0.0503 (12) | −0.0092 (10) | −0.0070 (10) | 0.0052 (10) |
C4 | 0.0485 (12) | 0.0329 (10) | 0.0534 (12) | −0.0045 (10) | −0.0046 (10) | 0.0085 (9) |
C5 | 0.0392 (11) | 0.0425 (11) | 0.0416 (11) | −0.0045 (10) | 0.0020 (9) | 0.0124 (9) |
C6 | 0.0371 (10) | 0.0475 (11) | 0.0338 (9) | 0.0066 (10) | −0.0007 (8) | −0.0037 (9) |
C7 | 0.0633 (16) | 0.0618 (16) | 0.0492 (13) | 0.0230 (14) | −0.0232 (12) | −0.0141 (13) |
C8 | 0.0370 (10) | 0.0554 (13) | 0.0333 (9) | 0.0064 (11) | −0.0011 (8) | −0.0030 (9) |
C9 | 0.0480 (13) | 0.0601 (14) | 0.0397 (11) | 0.0018 (12) | 0.0041 (10) | 0.0037 (11) |
C10 | 0.0493 (14) | 0.0662 (18) | 0.0739 (18) | −0.0105 (14) | 0.0034 (14) | −0.0128 (15) |
C11 | 0.0412 (13) | 0.098 (3) | 0.0567 (16) | −0.0039 (15) | −0.0048 (12) | −0.0291 (16) |
C12 | 0.0441 (13) | 0.111 (3) | 0.0324 (10) | 0.0085 (16) | −0.0036 (10) | 0.0020 (13) |
C13 | 0.0424 (12) | 0.0692 (16) | 0.0433 (12) | 0.0031 (12) | −0.0041 (10) | 0.0091 (12) |
C14 | 0.0300 (9) | 0.0406 (10) | 0.0409 (10) | −0.0082 (9) | −0.0054 (8) | 0.0056 (9) |
C15 | 0.0308 (9) | 0.0420 (10) | 0.0373 (9) | 0.0017 (9) | −0.0035 (8) | 0.0004 (9) |
C16 | 0.0415 (12) | 0.0371 (11) | 0.0618 (14) | −0.0013 (10) | 0.0018 (11) | −0.0003 (10) |
C17 | 0.094 (3) | 0.0415 (14) | 0.103 (3) | 0.0113 (16) | 0.014 (2) | −0.0055 (16) |
C18 | 0.0291 (9) | 0.0333 (9) | 0.0336 (9) | 0.0007 (8) | −0.0003 (7) | 0.0026 (8) |
C19 | 0.0371 (11) | 0.0625 (14) | 0.0363 (10) | −0.0018 (11) | −0.0054 (9) | −0.0006 (10) |
C20 | 0.0534 (14) | 0.0777 (18) | 0.0318 (10) | −0.0022 (14) | 0.0012 (10) | −0.0048 (11) |
C21 | 0.0423 (12) | 0.0648 (15) | 0.0438 (11) | 0.0002 (12) | 0.0125 (10) | −0.0025 (12) |
C22 | 0.0296 (9) | 0.0508 (12) | 0.0478 (11) | −0.0013 (10) | 0.0011 (9) | −0.0001 (11) |
C23 | 0.0319 (9) | 0.0413 (10) | 0.0326 (9) | −0.0033 (9) | −0.0025 (8) | 0.0007 (8) |
C24 | 0.0268 (9) | 0.0460 (11) | 0.0348 (9) | 0.0022 (9) | 0.0032 (8) | 0.0052 (9) |
C25 | 0.0395 (12) | 0.0518 (14) | 0.0722 (17) | 0.0014 (11) | 0.0238 (12) | 0.0040 (13) |
O2 | 0.0544 (11) | 0.0513 (10) | 0.0683 (11) | −0.0046 (9) | 0.0206 (10) | −0.0104 (9) |
O3 | 0.0371 (8) | 0.0556 (10) | 0.0602 (10) | −0.0079 (8) | 0.0126 (8) | −0.0119 (9) |
F1A | 0.096 (4) | 0.091 (4) | 0.184 (8) | 0.065 (4) | 0.098 (5) | 0.083 (5) |
F2A | 0.081 (3) | 0.130 (3) | 0.0511 (16) | 0.015 (2) | 0.0311 (15) | 0.017 (2) |
F3A | 0.0594 (11) | 0.0963 (15) | 0.136 (2) | −0.0175 (12) | 0.0426 (13) | 0.0020 (15) |
F1B | 0.036 (2) | 0.127 (6) | 0.086 (5) | 0.023 (3) | 0.006 (3) | 0.009 (5) |
F2B | 0.070 (6) | 0.26 (2) | 0.131 (9) | −0.056 (9) | 0.048 (6) | −0.155 (12) |
C1—N1 | 1.505 (2) | C11—C12 | 1.395 (5) |
C1—C2 | 1.530 (3) | C11—H11A | 0.9400 |
C1—H1A | 0.9800 | C12—C13 | 1.382 (4) |
C1—H1B | 0.9800 | C12—H12A | 0.9400 |
O1—C15 | 1.226 (3) | C13—H13A | 0.9400 |
N1—C6 | 1.504 (3) | C14—H14A | 0.9800 |
N1—C5 | 1.510 (3) | C14—H14B | 0.9800 |
N1—H1 | 0.91 (3) | C15—C16 | 1.517 (3) |
N2—C15 | 1.364 (3) | C16—C17 | 1.506 (4) |
N2—C18 | 1.443 (2) | C16—H16A | 0.9800 |
N2—C14 | 1.472 (3) | C16—H16B | 0.9800 |
C2—C3 | 1.529 (3) | C17—H17A | 0.9700 |
C2—C14 | 1.530 (3) | C17—H17B | 0.9700 |
C2—H2A | 0.9900 | C17—H17C | 0.9700 |
C3—C4 | 1.528 (3) | C18—C23 | 1.392 (3) |
C3—H3A | 0.9800 | C18—C19 | 1.395 (3) |
C3—H3B | 0.9800 | C19—C20 | 1.389 (4) |
C4—C5 | 1.519 (3) | C19—H19A | 0.9400 |
C4—H4A | 0.9800 | C20—C21 | 1.391 (4) |
C4—H4B | 0.9800 | C20—H20A | 0.9400 |
C5—H5A | 0.9800 | C21—C22 | 1.380 (3) |
C5—H5B | 0.9800 | C21—H21A | 0.9400 |
C6—C7 | 1.524 (3) | C22—C23 | 1.389 (3) |
C6—H6A | 0.9800 | C22—H22A | 0.9400 |
C6—H6B | 0.9800 | C23—H23A | 0.9400 |
C7—C8 | 1.520 (3) | C24—O2 | 1.222 (3) |
C7—H7A | 0.9800 | C24—O3 | 1.244 (3) |
C7—H7B | 0.9800 | C24—C25 | 1.550 (3) |
C8—C9 | 1.393 (4) | C25—F2B | 1.184 (8) |
C8—C13 | 1.394 (3) | C25—F1A | 1.256 (4) |
C9—C10 | 1.382 (4) | C25—F3A | 1.318 (3) |
C9—H9A | 0.9400 | C25—F2A | 1.423 (5) |
C10—C11 | 1.363 (5) | C25—F1B | 1.506 (7) |
C10—H10A | 0.9400 | ||
N1—C1—C2 | 109.37 (16) | C13—C12—C11 | 120.4 (3) |
N1—C1—H1A | 109.8 | C13—C12—H12A | 119.8 |
C2—C1—H1A | 109.8 | C11—C12—H12A | 119.8 |
N1—C1—H1B | 109.8 | C12—C13—C8 | 120.3 (3) |
C2—C1—H1B | 109.8 | C12—C13—H13A | 119.8 |
H1A—C1—H1B | 108.2 | C8—C13—H13A | 119.8 |
C6—N1—C1 | 111.20 (16) | N2—C14—C2 | 112.98 (16) |
C6—N1—C5 | 112.91 (16) | N2—C14—H14A | 109.0 |
C1—N1—C5 | 111.06 (16) | C2—C14—H14A | 109.0 |
C6—N1—H1 | 104.6 (15) | N2—C14—H14B | 109.0 |
C1—N1—H1 | 101.8 (15) | C2—C14—H14B | 109.0 |
C5—N1—H1 | 114.6 (16) | H14A—C14—H14B | 107.8 |
C15—N2—C18 | 123.27 (17) | O1—C15—N2 | 121.6 (2) |
C15—N2—C14 | 120.20 (17) | O1—C15—C16 | 122.0 (2) |
C18—N2—C14 | 116.53 (17) | N2—C15—C16 | 116.37 (18) |
C3—C2—C14 | 111.92 (17) | C17—C16—C15 | 113.6 (2) |
C3—C2—C1 | 110.06 (17) | C17—C16—H16A | 108.8 |
C14—C2—C1 | 111.01 (17) | C15—C16—H16A | 108.8 |
C3—C2—H2A | 107.9 | C17—C16—H16B | 108.8 |
C14—C2—H2A | 107.9 | C15—C16—H16B | 108.8 |
C1—C2—H2A | 107.9 | H16A—C16—H16B | 107.7 |
C4—C3—C2 | 110.17 (19) | C16—C17—H17A | 109.5 |
C4—C3—H3A | 109.6 | C16—C17—H17B | 109.5 |
C2—C3—H3A | 109.6 | H17A—C17—H17B | 109.5 |
C4—C3—H3B | 109.6 | C16—C17—H17C | 109.5 |
C2—C3—H3B | 109.6 | H17A—C17—H17C | 109.5 |
H3A—C3—H3B | 108.1 | H17B—C17—H17C | 109.5 |
C5—C4—C3 | 112.1 (2) | C23—C18—C19 | 119.77 (19) |
C5—C4—H4A | 109.2 | C23—C18—N2 | 120.32 (17) |
C3—C4—H4A | 109.2 | C19—C18—N2 | 119.86 (18) |
C5—C4—H4B | 109.2 | C20—C19—C18 | 119.9 (2) |
C3—C4—H4B | 109.2 | C20—C19—H19A | 120.1 |
H4A—C4—H4B | 107.9 | C18—C19—H19A | 120.1 |
N1—C5—C4 | 111.21 (17) | C19—C20—C21 | 120.2 (2) |
N1—C5—H5A | 109.4 | C19—C20—H20A | 119.9 |
C4—C5—H5A | 109.4 | C21—C20—H20A | 119.9 |
N1—C5—H5B | 109.4 | C22—C21—C20 | 119.7 (2) |
C4—C5—H5B | 109.4 | C22—C21—H21A | 120.1 |
H5A—C5—H5B | 108.0 | C20—C21—H21A | 120.1 |
N1—C6—C7 | 111.12 (18) | C21—C22—C23 | 120.7 (2) |
N1—C6—H6A | 109.4 | C21—C22—H22A | 119.7 |
C7—C6—H6A | 109.4 | C23—C22—H22A | 119.7 |
N1—C6—H6B | 109.4 | C22—C23—C18 | 119.75 (18) |
C7—C6—H6B | 109.4 | C22—C23—H23A | 120.1 |
H6A—C6—H6B | 108.0 | C18—C23—H23A | 120.1 |
C8—C7—C6 | 114.0 (2) | O2—C24—O3 | 129.9 (2) |
C8—C7—H7A | 108.8 | O2—C24—C25 | 116.5 (2) |
C6—C7—H7A | 108.8 | O3—C24—C25 | 113.6 (2) |
C8—C7—H7B | 108.8 | F2B—C25—F1A | 50.2 (8) |
C6—C7—H7B | 108.8 | F2B—C25—F3A | 122.0 (7) |
H7A—C7—H7B | 107.7 | F1A—C25—F3A | 117.3 (4) |
C9—C8—C13 | 118.3 (2) | F2B—C25—F2A | 53.2 (11) |
C9—C8—C7 | 121.2 (2) | F1A—C25—F2A | 102.8 (5) |
C13—C8—C7 | 120.4 (2) | F3A—C25—F2A | 94.6 (3) |
C10—C9—C8 | 120.9 (3) | F2B—C25—F1B | 99.8 (9) |
C10—C9—H9A | 119.6 | F1A—C25—F1B | 50.5 (4) |
C8—C9—H9A | 119.6 | F3A—C25—F1B | 85.3 (4) |
C11—C10—C9 | 120.6 (3) | F2A—C25—F1B | 147.6 (4) |
C11—C10—H10A | 119.7 | F2B—C25—C24 | 119.8 (5) |
C9—C10—H10A | 119.7 | F1A—C25—C24 | 116.5 (3) |
C10—C11—C12 | 119.5 (3) | F3A—C25—C24 | 114.9 (2) |
C10—C11—H11A | 120.3 | F2A—C25—C24 | 106.6 (3) |
C12—C11—H11A | 120.3 | F1B—C25—C24 | 102.8 (3) |
C2—C1—N1—C6 | −173.50 (16) | C14—N2—C15—O1 | −1.3 (3) |
C2—C1—N1—C5 | 59.9 (2) | C18—N2—C15—C16 | −1.4 (3) |
N1—C1—C2—C3 | −60.3 (2) | C14—N2—C15—C16 | 178.2 (2) |
N1—C1—C2—C14 | 175.23 (16) | O1—C15—C16—C17 | 6.0 (4) |
C14—C2—C3—C4 | −178.9 (2) | N2—C15—C16—C17 | −173.4 (3) |
C1—C2—C3—C4 | 57.1 (2) | C15—N2—C18—C23 | −85.5 (3) |
C2—C3—C4—C5 | −53.9 (3) | C14—N2—C18—C23 | 94.9 (2) |
C6—N1—C5—C4 | 177.84 (19) | C15—N2—C18—C19 | 97.2 (3) |
C1—N1—C5—C4 | −56.5 (2) | C14—N2—C18—C19 | −82.4 (3) |
C3—C4—C5—N1 | 53.4 (3) | C23—C18—C19—C20 | 0.6 (4) |
C1—N1—C6—C7 | 159.9 (2) | N2—C18—C19—C20 | 177.9 (2) |
C5—N1—C6—C7 | −74.5 (2) | C18—C19—C20—C21 | −0.8 (4) |
N1—C6—C7—C8 | −169.6 (2) | C19—C20—C21—C22 | 0.4 (5) |
C6—C7—C8—C9 | 54.2 (4) | C20—C21—C22—C23 | 0.1 (4) |
C6—C7—C8—C13 | −129.0 (3) | C21—C22—C23—C18 | −0.3 (4) |
C13—C8—C9—C10 | 0.2 (4) | C19—C18—C23—C22 | 0.0 (3) |
C7—C8—C9—C10 | 177.0 (3) | N2—C18—C23—C22 | −177.4 (2) |
C8—C9—C10—C11 | −0.5 (4) | O2—C24—C25—F2B | −164.3 (14) |
C9—C10—C11—C12 | 0.4 (4) | O3—C24—C25—F2B | 15.5 (14) |
C10—C11—C12—C13 | −0.1 (5) | O2—C24—C25—F1A | 138.3 (6) |
C11—C12—C13—C8 | −0.3 (4) | O3—C24—C25—F1A | −41.9 (7) |
C9—C8—C13—C12 | 0.2 (4) | O2—C24—C25—F3A | −4.4 (4) |
C7—C8—C13—C12 | −176.6 (3) | O3—C24—C25—F3A | 175.4 (3) |
C15—N2—C14—C2 | 109.1 (2) | O2—C24—C25—F2A | −107.7 (3) |
C18—N2—C14—C2 | −71.3 (2) | O3—C24—C25—F2A | 72.1 (3) |
C3—C2—C14—N2 | 173.01 (18) | O2—C24—C25—F1B | 86.3 (5) |
C1—C2—C14—N2 | −63.6 (2) | O3—C24—C25—F1B | −93.9 (5) |
C18—N2—C15—O1 | 179.20 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.91 (3) | 1.82 (3) | 2.722 (2) | 178 (2) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H31N2O+·C2F3O2− |
Mr | 464.52 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 213 |
a, b, c (Å) | 10.1973 (7), 10.8295 (7), 21.910 (1) |
V (Å3) | 2419.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15557, 3332, 3113 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.125, 1.10 |
No. of reflections | 3332 |
No. of parameters | 321 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.36 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.91 (3) | 1.82 (3) | 2.722 (2) | 178 (2) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
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