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The synthesis and crystal structure of the title compound, C25H31F3N2O3, are reported.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015654/om6150sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015654/om6150Isup2.hkl
Contains datablock I

CCDC reference: 222907

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](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

Comment top

NO COMMENT

Experimental top

The title compound was synthesized from ethyl (S)-nipecotate L-tartrate (see reaction Scheme). Crystals were grown from an ethyl acetate solution.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (50% probability) of the title compound.
(S)—N-(1-Phenethylpiperidin-1-ium-3-ylmethyl)-N-phenylpropionamide trifluoroacetate top
Crystal data top
C23H31N2O+·C2F3O2Dx = 1.275 Mg m3
Mr = 464.52Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 648 reflections
a = 10.1973 (7) Åθ = 3.0–28.7°
b = 10.8295 (7) ŵ = 0.10 mm1
c = 21.910 (1) ÅT = 213 K
V = 2419.6 (3) Å3Needle, colorless
Z = 40.25 × 0.20 × 0.10 mm
F(000) = 984
Data collection top
Bruker CCD
diffractometer
3113 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 28.3°, θmin = 1.9°
Detector resolution: 8.3 pixels mm-1h = 1313
ω scansk = 149
15557 measured reflectionsl = 2826
3332 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H 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 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C23H31N2O+·C2F3O2V = 2419.6 (3) Å3
Mr = 464.52Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.1973 (7) ŵ = 0.10 mm1
b = 10.8295 (7) ÅT = 213 K
c = 21.910 (1) Å0.25 × 0.20 × 0.10 mm
Data collection top
Bruker CCD
diffractometer
3113 reflections with I > 2σ(I)
15557 measured reflectionsRint = 0.055
3332 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.40 e Å3
3332 reflectionsΔρmin = 0.36 e Å3
321 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.77365 (19)0.6452 (2)0.25998 (9)0.0335 (4)
H1A0.85990.64170.24040.040*
H1B0.74410.56040.26750.040*
O10.97375 (17)0.42215 (18)0.32919 (8)0.0510 (4)
N10.67772 (16)0.71023 (16)0.21882 (7)0.0311 (3)
H10.602 (3)0.704 (2)0.2403 (11)0.029 (6)*
N20.81872 (16)0.52443 (16)0.38306 (8)0.0334 (4)
C20.78372 (19)0.71502 (19)0.32052 (9)0.0322 (4)
H2A0.69470.71990.33840.039*
C30.8317 (2)0.8468 (2)0.30927 (11)0.0436 (5)
H3A0.83470.89190.34800.052*
H3B0.92060.84470.29230.052*
C40.7400 (3)0.9130 (2)0.26492 (11)0.0449 (5)
H4A0.65460.92530.28450.054*
H4B0.77620.99460.25530.054*
C50.7211 (2)0.8410 (2)0.20607 (10)0.0411 (5)
H5A0.65510.88240.18080.049*
H5B0.80370.83960.18320.049*
C60.6530 (2)0.6370 (2)0.16163 (9)0.0395 (5)
H6A0.64900.54900.17170.047*
H6B0.72570.64950.13310.047*
C70.5250 (3)0.6761 (3)0.13135 (13)0.0581 (7)
H7A0.45590.67890.16240.070*
H7B0.53550.75970.11500.070*
C80.4811 (2)0.5912 (2)0.08004 (10)0.0419 (5)
C90.4668 (3)0.4647 (3)0.08934 (11)0.0493 (6)
H9A0.48860.43050.12750.059*
C100.4211 (3)0.3888 (3)0.04330 (15)0.0631 (8)
H10A0.41270.30350.05030.076*
C110.3881 (3)0.4365 (4)0.01218 (14)0.0652 (9)
H11A0.35650.38450.04330.078*
C120.4016 (3)0.5629 (4)0.02249 (11)0.0626 (8)
H12A0.37900.59620.06070.075*
C130.4479 (2)0.6395 (3)0.02312 (11)0.0516 (6)
H13A0.45700.72460.01570.062*
C140.8715 (2)0.6460 (2)0.36570 (10)0.0372 (4)
H14A0.95840.63480.34740.045*
H14B0.88210.69630.40250.045*
C150.8777 (2)0.4190 (2)0.36282 (10)0.0367 (4)
C160.8188 (2)0.2982 (2)0.38471 (13)0.0468 (5)
H16A0.81150.30060.42930.056*
H16B0.73010.29030.36800.056*
C170.8974 (4)0.1863 (3)0.3667 (2)0.0798 (11)
H17A0.85460.11250.38190.120*
H17B0.98480.19220.38390.120*
H17C0.90340.18210.32250.120*
C180.70467 (19)0.52458 (19)0.42202 (9)0.0320 (4)
C190.7195 (2)0.5384 (3)0.48496 (10)0.0453 (5)
H19A0.80370.54490.50210.054*
C200.6095 (3)0.5426 (3)0.52228 (11)0.0543 (7)
H20A0.61940.55100.56470.065*
C210.4846 (3)0.5345 (3)0.49701 (11)0.0503 (6)
H21A0.41020.53800.52230.060*
C220.4704 (2)0.5214 (2)0.43472 (11)0.0427 (5)
H22A0.38600.51610.41770.051*
C230.5796 (2)0.5161 (2)0.39692 (9)0.0353 (4)
H23A0.56900.50680.35450.042*
C240.6211 (2)0.2773 (2)0.22002 (10)0.0358 (4)
C250.7464 (3)0.2675 (3)0.18029 (14)0.0545 (7)
O20.6075 (2)0.37242 (18)0.24934 (10)0.0580 (5)
O30.54885 (17)0.18503 (18)0.21666 (9)0.0510 (4)
F1A0.8041 (6)0.1650 (5)0.1804 (4)0.124 (4)0.652 (10)
F2A0.7053 (5)0.2798 (5)0.11853 (14)0.0872 (14)0.652 (10)
F3A0.8201 (2)0.3675 (2)0.17958 (13)0.0973 (8)
F1B0.8463 (5)0.2175 (9)0.2244 (4)0.083 (3)0.348 (10)
F2B0.7531 (9)0.1915 (18)0.1416 (7)0.153 (9)0.348 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0266 (9)0.0381 (10)0.0357 (9)0.0026 (8)0.0002 (7)0.0028 (8)
O10.0375 (8)0.0587 (10)0.0567 (9)0.0022 (8)0.0122 (8)0.0017 (9)
N10.0254 (7)0.0369 (8)0.0308 (7)0.0013 (7)0.0025 (6)0.0026 (7)
N20.0262 (7)0.0364 (8)0.0377 (8)0.0022 (7)0.0009 (7)0.0061 (7)
C20.0274 (8)0.0336 (9)0.0355 (9)0.0031 (8)0.0005 (8)0.0027 (8)
C30.0412 (11)0.0394 (11)0.0503 (12)0.0092 (10)0.0070 (10)0.0052 (10)
C40.0485 (12)0.0329 (10)0.0534 (12)0.0045 (10)0.0046 (10)0.0085 (9)
C50.0392 (11)0.0425 (11)0.0416 (11)0.0045 (10)0.0020 (9)0.0124 (9)
C60.0371 (10)0.0475 (11)0.0338 (9)0.0066 (10)0.0007 (8)0.0037 (9)
C70.0633 (16)0.0618 (16)0.0492 (13)0.0230 (14)0.0232 (12)0.0141 (13)
C80.0370 (10)0.0554 (13)0.0333 (9)0.0064 (11)0.0011 (8)0.0030 (9)
C90.0480 (13)0.0601 (14)0.0397 (11)0.0018 (12)0.0041 (10)0.0037 (11)
C100.0493 (14)0.0662 (18)0.0739 (18)0.0105 (14)0.0034 (14)0.0128 (15)
C110.0412 (13)0.098 (3)0.0567 (16)0.0039 (15)0.0048 (12)0.0291 (16)
C120.0441 (13)0.111 (3)0.0324 (10)0.0085 (16)0.0036 (10)0.0020 (13)
C130.0424 (12)0.0692 (16)0.0433 (12)0.0031 (12)0.0041 (10)0.0091 (12)
C140.0300 (9)0.0406 (10)0.0409 (10)0.0082 (9)0.0054 (8)0.0056 (9)
C150.0308 (9)0.0420 (10)0.0373 (9)0.0017 (9)0.0035 (8)0.0004 (9)
C160.0415 (12)0.0371 (11)0.0618 (14)0.0013 (10)0.0018 (11)0.0003 (10)
C170.094 (3)0.0415 (14)0.103 (3)0.0113 (16)0.014 (2)0.0055 (16)
C180.0291 (9)0.0333 (9)0.0336 (9)0.0007 (8)0.0003 (7)0.0026 (8)
C190.0371 (11)0.0625 (14)0.0363 (10)0.0018 (11)0.0054 (9)0.0006 (10)
C200.0534 (14)0.0777 (18)0.0318 (10)0.0022 (14)0.0012 (10)0.0048 (11)
C210.0423 (12)0.0648 (15)0.0438 (11)0.0002 (12)0.0125 (10)0.0025 (12)
C220.0296 (9)0.0508 (12)0.0478 (11)0.0013 (10)0.0011 (9)0.0001 (11)
C230.0319 (9)0.0413 (10)0.0326 (9)0.0033 (9)0.0025 (8)0.0007 (8)
C240.0268 (9)0.0460 (11)0.0348 (9)0.0022 (9)0.0032 (8)0.0052 (9)
C250.0395 (12)0.0518 (14)0.0722 (17)0.0014 (11)0.0238 (12)0.0040 (13)
O20.0544 (11)0.0513 (10)0.0683 (11)0.0046 (9)0.0206 (10)0.0104 (9)
O30.0371 (8)0.0556 (10)0.0602 (10)0.0079 (8)0.0126 (8)0.0119 (9)
F1A0.096 (4)0.091 (4)0.184 (8)0.065 (4)0.098 (5)0.083 (5)
F2A0.081 (3)0.130 (3)0.0511 (16)0.015 (2)0.0311 (15)0.017 (2)
F3A0.0594 (11)0.0963 (15)0.136 (2)0.0175 (12)0.0426 (13)0.0020 (15)
F1B0.036 (2)0.127 (6)0.086 (5)0.023 (3)0.006 (3)0.009 (5)
F2B0.070 (6)0.26 (2)0.131 (9)0.056 (9)0.048 (6)0.155 (12)
Geometric parameters (Å, º) top
C1—N11.505 (2)C11—C121.395 (5)
C1—C21.530 (3)C11—H11A0.9400
C1—H1A0.9800C12—C131.382 (4)
C1—H1B0.9800C12—H12A0.9400
O1—C151.226 (3)C13—H13A0.9400
N1—C61.504 (3)C14—H14A0.9800
N1—C51.510 (3)C14—H14B0.9800
N1—H10.91 (3)C15—C161.517 (3)
N2—C151.364 (3)C16—C171.506 (4)
N2—C181.443 (2)C16—H16A0.9800
N2—C141.472 (3)C16—H16B0.9800
C2—C31.529 (3)C17—H17A0.9700
C2—C141.530 (3)C17—H17B0.9700
C2—H2A0.9900C17—H17C0.9700
C3—C41.528 (3)C18—C231.392 (3)
C3—H3A0.9800C18—C191.395 (3)
C3—H3B0.9800C19—C201.389 (4)
C4—C51.519 (3)C19—H19A0.9400
C4—H4A0.9800C20—C211.391 (4)
C4—H4B0.9800C20—H20A0.9400
C5—H5A0.9800C21—C221.380 (3)
C5—H5B0.9800C21—H21A0.9400
C6—C71.524 (3)C22—C231.389 (3)
C6—H6A0.9800C22—H22A0.9400
C6—H6B0.9800C23—H23A0.9400
C7—C81.520 (3)C24—O21.222 (3)
C7—H7A0.9800C24—O31.244 (3)
C7—H7B0.9800C24—C251.550 (3)
C8—C91.393 (4)C25—F2B1.184 (8)
C8—C131.394 (3)C25—F1A1.256 (4)
C9—C101.382 (4)C25—F3A1.318 (3)
C9—H9A0.9400C25—F2A1.423 (5)
C10—C111.363 (5)C25—F1B1.506 (7)
C10—H10A0.9400
N1—C1—C2109.37 (16)C13—C12—C11120.4 (3)
N1—C1—H1A109.8C13—C12—H12A119.8
C2—C1—H1A109.8C11—C12—H12A119.8
N1—C1—H1B109.8C12—C13—C8120.3 (3)
C2—C1—H1B109.8C12—C13—H13A119.8
H1A—C1—H1B108.2C8—C13—H13A119.8
C6—N1—C1111.20 (16)N2—C14—C2112.98 (16)
C6—N1—C5112.91 (16)N2—C14—H14A109.0
C1—N1—C5111.06 (16)C2—C14—H14A109.0
C6—N1—H1104.6 (15)N2—C14—H14B109.0
C1—N1—H1101.8 (15)C2—C14—H14B109.0
C5—N1—H1114.6 (16)H14A—C14—H14B107.8
C15—N2—C18123.27 (17)O1—C15—N2121.6 (2)
C15—N2—C14120.20 (17)O1—C15—C16122.0 (2)
C18—N2—C14116.53 (17)N2—C15—C16116.37 (18)
C3—C2—C14111.92 (17)C17—C16—C15113.6 (2)
C3—C2—C1110.06 (17)C17—C16—H16A108.8
C14—C2—C1111.01 (17)C15—C16—H16A108.8
C3—C2—H2A107.9C17—C16—H16B108.8
C14—C2—H2A107.9C15—C16—H16B108.8
C1—C2—H2A107.9H16A—C16—H16B107.7
C4—C3—C2110.17 (19)C16—C17—H17A109.5
C4—C3—H3A109.6C16—C17—H17B109.5
C2—C3—H3A109.6H17A—C17—H17B109.5
C4—C3—H3B109.6C16—C17—H17C109.5
C2—C3—H3B109.6H17A—C17—H17C109.5
H3A—C3—H3B108.1H17B—C17—H17C109.5
C5—C4—C3112.1 (2)C23—C18—C19119.77 (19)
C5—C4—H4A109.2C23—C18—N2120.32 (17)
C3—C4—H4A109.2C19—C18—N2119.86 (18)
C5—C4—H4B109.2C20—C19—C18119.9 (2)
C3—C4—H4B109.2C20—C19—H19A120.1
H4A—C4—H4B107.9C18—C19—H19A120.1
N1—C5—C4111.21 (17)C19—C20—C21120.2 (2)
N1—C5—H5A109.4C19—C20—H20A119.9
C4—C5—H5A109.4C21—C20—H20A119.9
N1—C5—H5B109.4C22—C21—C20119.7 (2)
C4—C5—H5B109.4C22—C21—H21A120.1
H5A—C5—H5B108.0C20—C21—H21A120.1
N1—C6—C7111.12 (18)C21—C22—C23120.7 (2)
N1—C6—H6A109.4C21—C22—H22A119.7
C7—C6—H6A109.4C23—C22—H22A119.7
N1—C6—H6B109.4C22—C23—C18119.75 (18)
C7—C6—H6B109.4C22—C23—H23A120.1
H6A—C6—H6B108.0C18—C23—H23A120.1
C8—C7—C6114.0 (2)O2—C24—O3129.9 (2)
C8—C7—H7A108.8O2—C24—C25116.5 (2)
C6—C7—H7A108.8O3—C24—C25113.6 (2)
C8—C7—H7B108.8F2B—C25—F1A50.2 (8)
C6—C7—H7B108.8F2B—C25—F3A122.0 (7)
H7A—C7—H7B107.7F1A—C25—F3A117.3 (4)
C9—C8—C13118.3 (2)F2B—C25—F2A53.2 (11)
C9—C8—C7121.2 (2)F1A—C25—F2A102.8 (5)
C13—C8—C7120.4 (2)F3A—C25—F2A94.6 (3)
C10—C9—C8120.9 (3)F2B—C25—F1B99.8 (9)
C10—C9—H9A119.6F1A—C25—F1B50.5 (4)
C8—C9—H9A119.6F3A—C25—F1B85.3 (4)
C11—C10—C9120.6 (3)F2A—C25—F1B147.6 (4)
C11—C10—H10A119.7F2B—C25—C24119.8 (5)
C9—C10—H10A119.7F1A—C25—C24116.5 (3)
C10—C11—C12119.5 (3)F3A—C25—C24114.9 (2)
C10—C11—H11A120.3F2A—C25—C24106.6 (3)
C12—C11—H11A120.3F1B—C25—C24102.8 (3)
C2—C1—N1—C6173.50 (16)C14—N2—C15—O11.3 (3)
C2—C1—N1—C559.9 (2)C18—N2—C15—C161.4 (3)
N1—C1—C2—C360.3 (2)C14—N2—C15—C16178.2 (2)
N1—C1—C2—C14175.23 (16)O1—C15—C16—C176.0 (4)
C14—C2—C3—C4178.9 (2)N2—C15—C16—C17173.4 (3)
C1—C2—C3—C457.1 (2)C15—N2—C18—C2385.5 (3)
C2—C3—C4—C553.9 (3)C14—N2—C18—C2394.9 (2)
C6—N1—C5—C4177.84 (19)C15—N2—C18—C1997.2 (3)
C1—N1—C5—C456.5 (2)C14—N2—C18—C1982.4 (3)
C3—C4—C5—N153.4 (3)C23—C18—C19—C200.6 (4)
C1—N1—C6—C7159.9 (2)N2—C18—C19—C20177.9 (2)
C5—N1—C6—C774.5 (2)C18—C19—C20—C210.8 (4)
N1—C6—C7—C8169.6 (2)C19—C20—C21—C220.4 (5)
C6—C7—C8—C954.2 (4)C20—C21—C22—C230.1 (4)
C6—C7—C8—C13129.0 (3)C21—C22—C23—C180.3 (4)
C13—C8—C9—C100.2 (4)C19—C18—C23—C220.0 (3)
C7—C8—C9—C10177.0 (3)N2—C18—C23—C22177.4 (2)
C8—C9—C10—C110.5 (4)O2—C24—C25—F2B164.3 (14)
C9—C10—C11—C120.4 (4)O3—C24—C25—F2B15.5 (14)
C10—C11—C12—C130.1 (5)O2—C24—C25—F1A138.3 (6)
C11—C12—C13—C80.3 (4)O3—C24—C25—F1A41.9 (7)
C9—C8—C13—C120.2 (4)O2—C24—C25—F3A4.4 (4)
C7—C8—C13—C12176.6 (3)O3—C24—C25—F3A175.4 (3)
C15—N2—C14—C2109.1 (2)O2—C24—C25—F2A107.7 (3)
C18—N2—C14—C271.3 (2)O3—C24—C25—F2A72.1 (3)
C3—C2—C14—N2173.01 (18)O2—C24—C25—F1B86.3 (5)
C1—C2—C14—N263.6 (2)O3—C24—C25—F1B93.9 (5)
C18—N2—C15—O1179.20 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.91 (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 formulaC23H31N2O+·C2F3O2
Mr464.52
Crystal system, space groupOrthorhombic, P212121
Temperature (K)213
a, b, c (Å)10.1973 (7), 10.8295 (7), 21.910 (1)
V3)2419.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.10
Data collection
DiffractometerBruker CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15557, 3332, 3113
Rint0.055
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.125, 1.10
No. of reflections3332
No. of parameters321
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.36

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.91 (3)1.82 (3)2.722 (2)178 (2)
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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