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The 2-amino-4,6-diphenyl-4H-1,3-oxazinium trifluoro­acetate ion pairs in the title compound, C16H15N2O+·C2F3O2, are held together by two N—H...O hydrogen bonds [Namino—H...O and Noxazinium—H...O], and adjacent ion pairs are linked into helical chains by a third and substantially weaker Namino—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027376/ob6578sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027376/ob6578Isup2.hkl
Contains datablock I

CCDC reference: 287680

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in solvent or counterion
  • R factor = 0.045
  • wR factor = 0.115
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F1' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F2' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F3' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F4' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F5' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F6' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C19 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C20 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F4 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C21 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C22 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.30 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C7' -C12' 1.37 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.10 Deg. F1 -C19 -F1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.40 Deg. F6' -C21 -F4 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C2 F3 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 24 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 17 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Domino (Tietze, 1996; Armstrong et al., 1996; Tietze & Modi, 2000) and multicomponent (Dömling & Ugi, 2000; Kappe, 2000; Bienaymé et al., 2000; Jacobi von Wangelin et al., 2003; Simon et al., 2004) reactions (MCRs) are powerful strategies in current organic synthesis. Consistently, several reported MCRs feature Diels–Alder chemistry with heterodiene (Batey et al., 1999; Tailor & Hall, 2000; Touré et al., 2003; Tietze & Rachkelmann, 2004; Strübing et al., 2005) building blocks for the synthesis of heterocyclic six-membered rings. Recently, we synthesized a series of 2-amino-4H-1,3-oxazines and 2-amino-4H-1,3-thiazines (Huang et al., 2005). 4H-1,3-Oxazines and 4H-1,3-thiazines are important synthetic intermediates in organic synthesis (Schmidt, 1972; Jochims et al., 1990; Vanier et al., 2004), and these skeletons have been found in a few biologically relevant compounds (Ilyuchenok et al., 1979; Eckstein & Urbanski, 1963; Eckstein & Urbanski, 1978; Sondhi et al., 2000) and vulcanization accelerators (Gridunov et al., 1972). Since the Diels–Alder reaction may yield other stereoisomers, we wish to confirm the structure of a product of the reaction, 2-amino-4,6-diphenyl-4H-1,3-oxazine. Unfortunately, we have not obtained any crystal. Therefore, we prepared crystals of its salt with trifluoroacetic acid, namely the title compound, (I).

There are two independent ion pairs (Fig. 1). The C—O bond lengths of the anions [1.215 (2)–1.227 (2) Å] indicate that the original trifluoroacetic group turns out to be the trifluoroacetate one with a form of full delocalization of electrons. Similarly, the N3—C2/N3'—C2' [1.299 (2) and 1.307 (2) Å] and N19—C2/N19'—C2' bond lengths [1.297 (3) and 1.296 (3) Å], and the angles of the heterocyclic rings, are consistent with the iminium tautomer and suggest intensive protonation of the heterocycle.

A network of intermolecular N—H···O interactions (Fig. 2) provide strong packing directives in (I). The ion pairs are held together by two N—H···O hydrogen bonds [Table 2; N···O = 2.766 (2)–2.778 (3) Å], and adjacent ion-pairs are linked into helical chains by a third and substantially weaker N—H···O hydrogen bond [N···O = 2.820–2.823 (2) Å].

Experimental top

2-Amino-4,6-diphenyl-4H-1,3-oxazine was prepared as described by Huang et al. (2005). Crystals of (I) appropriate for data collection were obtained by slow evaporation from an N,N-dimethylformide (3 ml) and trifluoroacetic acid (1 ml) solution of 2-amino-4,6-diphenyl-4H-1,3-oxazine (20 mg) at room temperature over a period of a week.

Refinement top

The CF3 groups of the anions are disordered, with three of the F atoms distributed over two sites (F1/F2/F3 and F1'/F2'/F3'; F4/F5/F6 and F4'/F5'/F6'), their occupation factors being 50% each estimated on the basis of Ueq values. The disordered parts of the anions were constrained to a chemically reasonable geometry. H atoms bonded to the N atoms were located in difference Fourier maps and their parameters were refined with N—H distances restrained to 0.86 (1) Å. The positions of the C-bound H atoms were calculated geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL/PC (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Figures top
[Figure 1] Fig. 1. A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the b axis. Hydrogen bonds are indicated by dashed lines. H atoms not involved in hydrogen bonding have been omitted.
2-Amino-4,6-diphenyl-4H-1,3-oxazinium trifluoroacetate top
Crystal data top
C16H15N2O+·C2F3O2Z = 4
Mr = 364.32F(000) = 752
Triclinic, P1Dx = 1.370 Mg m3
a = 10.341 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.867 (2) ÅCell parameters from 30 reflections
c = 14.409 (3) Åθ = 6.6–13.7°
α = 90.62 (2)°µ = 0.12 mm1
β = 92.68 (2)°T = 296 K
γ = 91.03 (2)°Block, colorless
V = 1765.9 (6) Å30.58 × 0.50 × 0.42 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.012
Radiation source: normal-focus sealed tubeθmax = 25.5°, θmin = 1.4°
Graphite monochromatorh = 012
ω scansk = 1414
7215 measured reflectionsl = 1717
6591 independent reflections3 standard reflections every 97 reflections
3495 reflections with I > 2σ(I) intensity decay: 2.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.056P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
6591 reflectionsΔρmax = 0.24 e Å3
548 parametersΔρmin = 0.18 e Å3
18 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0093 (9)
Crystal data top
C16H15N2O+·C2F3O2γ = 91.03 (2)°
Mr = 364.32V = 1765.9 (6) Å3
Triclinic, P1Z = 4
a = 10.341 (2) ÅMo Kα radiation
b = 11.867 (2) ŵ = 0.12 mm1
c = 14.409 (3) ÅT = 296 K
α = 90.62 (2)°0.58 × 0.50 × 0.42 mm
β = 92.68 (2)°
Data collection top
Siemens P4
diffractometer
Rint = 0.012
7215 measured reflections3 standard reflections every 97 reflections
6591 independent reflections intensity decay: 2.8%
3495 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.04518 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.24 e Å3
6591 reflectionsΔρmin = 0.18 e Å3
548 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.13372 (15)0.41354 (11)0.38593 (10)0.0638 (4)
N30.17320 (18)0.57413 (13)0.30349 (12)0.0562 (5)
N190.1284 (2)0.40313 (16)0.23251 (14)0.0720 (6)
C20.1467 (2)0.46677 (17)0.30585 (15)0.0539 (5)
C40.17696 (19)0.64979 (15)0.38423 (13)0.0494 (5)
H40.09530.69050.38370.059*
C50.18565 (19)0.58029 (16)0.46998 (14)0.0546 (5)
H50.20760.61640.52630.066*
C60.16398 (19)0.47118 (16)0.47022 (13)0.0506 (5)
C70.2868 (2)0.73550 (16)0.37983 (13)0.0505 (5)
C80.4010 (2)0.7115 (2)0.34138 (17)0.0745 (7)
H80.41270.64050.31540.089*
C90.5002 (3)0.7918 (3)0.34059 (19)0.0979 (9)
H90.57780.77460.31400.117*
C100.4838 (4)0.8958 (3)0.3789 (2)0.1064 (11)
H100.54980.94990.37810.128*
C110.3716 (4)0.9199 (2)0.4178 (2)0.1042 (10)
H110.36120.99030.44510.125*
C120.2719 (3)0.84089 (18)0.41759 (16)0.0780 (7)
H120.19400.85930.44320.094*
C130.16147 (19)0.39324 (17)0.54875 (15)0.0538 (5)
C140.1625 (2)0.43465 (19)0.63906 (15)0.0639 (6)
H140.16800.51200.65010.077*
C150.1556 (2)0.3620 (2)0.71248 (17)0.0772 (7)
H150.15610.39080.77280.093*
C160.1479 (2)0.2483 (2)0.69796 (19)0.0797 (8)
H160.14320.19990.74810.096*
C170.1472 (2)0.2056 (2)0.60895 (19)0.0760 (7)
H170.14180.12810.59890.091*
C180.1545 (2)0.27745 (18)0.53396 (16)0.0635 (6)
H180.15460.24810.47390.076*
O1'0.38790 (15)0.91519 (11)0.12108 (10)0.0652 (4)
N3'0.30266 (19)1.07470 (14)0.18416 (12)0.0582 (5)
N19'0.1875 (2)0.90784 (17)0.16759 (15)0.0732 (6)
C2'0.2914 (2)0.96871 (17)0.15883 (14)0.0562 (6)
C4'0.4096 (2)1.14887 (15)0.15889 (14)0.0535 (5)
H4'0.38271.18770.10170.064*
C5'0.5216 (2)1.07709 (17)0.13814 (13)0.0577 (6)
H5'0.60351.11090.13790.069*
C6'0.5106 (2)0.96857 (17)0.12016 (13)0.0552 (5)
C7'0.4421 (2)1.23721 (16)0.23282 (14)0.0521 (5)
C8'0.4342 (3)1.2180 (2)0.32543 (17)0.0855 (8)
H8'0.40381.14860.34540.103*
C9'0.4715 (3)1.3014 (3)0.39067 (18)0.0983 (9)
H9'0.46571.28740.45370.118*
C10'0.5160 (3)1.4027 (2)0.3622 (2)0.0886 (8)
H10'0.54071.45840.40570.106*
C11'0.5246 (3)1.4227 (2)0.2708 (2)0.0941 (9)
H11'0.55641.49190.25130.113*
C12'0.4864 (2)1.34141 (19)0.20655 (17)0.0774 (7)
H12'0.49061.35710.14370.093*
C13'0.6091 (2)0.88756 (18)0.09463 (13)0.0584 (6)
C14'0.7321 (2)0.9254 (2)0.07351 (15)0.0734 (7)
H14'0.75241.00210.07670.088*
C15'0.8248 (3)0.8495 (2)0.04775 (17)0.0858 (8)
H15'0.90700.87570.03410.103*
C16'0.7963 (3)0.7365 (2)0.04229 (17)0.0858 (8)
H16'0.85860.68620.02430.103*
C17'0.6758 (3)0.6976 (2)0.06342 (17)0.0825 (8)
H17'0.65690.62070.05990.099*
C18'0.5811 (2)0.77199 (18)0.09023 (14)0.0686 (6)
H18'0.49990.74480.10510.082*
F10.2110 (5)0.0897 (4)0.3387 (6)0.1025 (19)0.50
F20.0952 (5)0.2229 (9)0.3818 (5)0.138 (2)0.50
F30.1912 (7)0.2219 (9)0.2479 (5)0.145 (2)0.50
F40.2126 (10)0.5916 (5)0.0966 (3)0.106 (2)0.50
F50.2788 (7)0.7391 (6)0.0328 (4)0.1047 (18)0.50
F60.0766 (5)0.7106 (8)0.0597 (4)0.1160 (17)0.50
F1'0.2370 (5)0.1165 (9)0.2830 (9)0.178 (4)0.50
F2'0.1060 (8)0.1279 (8)0.3972 (3)0.182 (3)0.50
F3'0.1219 (7)0.2687 (3)0.3121 (9)0.140 (2)0.50
F4'0.3094 (4)0.6606 (12)0.0492 (5)0.187 (3)0.50
F5'0.1533 (14)0.7689 (4)0.0336 (4)0.153 (3)0.50
F6'0.1272 (12)0.6085 (7)0.1000 (4)0.158 (4)0.50
O30.08434 (16)0.16962 (12)0.25383 (12)0.0794 (5)
O40.02405 (19)0.00811 (15)0.24309 (18)0.1333 (9)
O50.17392 (18)0.67401 (12)0.13046 (10)0.0832 (5)
O60.1688 (3)0.50667 (14)0.06404 (12)0.1284 (9)
C190.1225 (2)0.1586 (2)0.30835 (19)0.0816 (8)
C200.0095 (2)0.10709 (19)0.26460 (16)0.0673 (6)
C210.1858 (3)0.66211 (19)0.02943 (15)0.0762 (7)
C220.1751 (2)0.60897 (19)0.06415 (15)0.0669 (6)
H3N0.1758 (19)0.6059 (15)0.2493 (9)0.061 (6)*
H3'N0.2361 (14)1.1058 (16)0.2079 (14)0.068 (7)*
H19A0.114 (2)0.3313 (9)0.2396 (15)0.075 (7)*
H19B0.137 (2)0.4320 (18)0.1771 (9)0.090 (9)*
H19C0.186 (2)0.8359 (10)0.1524 (17)0.105 (9)*
H19D0.1187 (15)0.9347 (18)0.1918 (15)0.082 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0909 (12)0.0456 (8)0.0541 (9)0.0141 (7)0.0006 (8)0.0044 (7)
N30.0781 (13)0.0435 (10)0.0464 (11)0.0096 (9)0.0028 (10)0.0009 (8)
N190.1141 (18)0.0458 (12)0.0552 (13)0.0153 (12)0.0015 (12)0.0034 (10)
C20.0609 (14)0.0454 (12)0.0550 (14)0.0064 (10)0.0017 (11)0.0010 (11)
C40.0531 (13)0.0438 (11)0.0513 (12)0.0014 (10)0.0042 (10)0.0002 (9)
C50.0608 (14)0.0526 (12)0.0503 (12)0.0093 (11)0.0069 (10)0.0024 (10)
C60.0495 (13)0.0533 (13)0.0487 (12)0.0060 (10)0.0022 (10)0.0000 (10)
C70.0604 (14)0.0473 (12)0.0435 (11)0.0082 (10)0.0025 (10)0.0021 (9)
C80.0605 (16)0.0807 (17)0.0821 (17)0.0096 (14)0.0071 (13)0.0034 (13)
C90.0648 (18)0.146 (3)0.0818 (19)0.0307 (19)0.0042 (14)0.0040 (19)
C100.127 (3)0.113 (3)0.076 (2)0.068 (2)0.0051 (19)0.0106 (18)
C110.154 (3)0.0689 (18)0.089 (2)0.045 (2)0.014 (2)0.0091 (15)
C120.102 (2)0.0553 (14)0.0770 (17)0.0175 (14)0.0200 (15)0.0072 (12)
C130.0466 (13)0.0543 (13)0.0606 (14)0.0035 (10)0.0016 (10)0.0107 (11)
C140.0656 (15)0.0663 (14)0.0589 (15)0.0094 (12)0.0021 (12)0.0088 (12)
C150.0776 (18)0.0915 (19)0.0617 (16)0.0112 (15)0.0062 (13)0.0177 (14)
C160.0691 (17)0.092 (2)0.0780 (19)0.0058 (14)0.0071 (14)0.0369 (15)
C170.0698 (17)0.0627 (15)0.095 (2)0.0005 (13)0.0028 (15)0.0237 (15)
C180.0633 (15)0.0590 (14)0.0680 (15)0.0009 (11)0.0005 (12)0.0126 (11)
O1'0.0694 (11)0.0505 (8)0.0757 (10)0.0039 (8)0.0064 (8)0.0161 (7)
N3'0.0643 (13)0.0455 (10)0.0651 (12)0.0004 (10)0.0097 (10)0.0128 (9)
N19'0.0755 (16)0.0525 (13)0.0920 (15)0.0073 (12)0.0160 (13)0.0165 (11)
C2'0.0661 (16)0.0497 (13)0.0525 (13)0.0030 (12)0.0031 (11)0.0074 (10)
C4'0.0658 (14)0.0457 (11)0.0492 (12)0.0007 (11)0.0044 (11)0.0026 (9)
C5'0.0639 (15)0.0559 (13)0.0535 (13)0.0012 (11)0.0071 (11)0.0061 (10)
C6'0.0665 (16)0.0559 (13)0.0431 (12)0.0027 (12)0.0013 (10)0.0044 (10)
C7'0.0551 (13)0.0463 (12)0.0549 (13)0.0055 (10)0.0029 (10)0.0052 (10)
C8'0.131 (2)0.0661 (15)0.0583 (16)0.0073 (15)0.0053 (15)0.0035 (12)
C9'0.131 (3)0.101 (2)0.0609 (16)0.001 (2)0.0135 (16)0.0184 (16)
C10'0.083 (2)0.0778 (19)0.103 (2)0.0028 (15)0.0053 (17)0.0393 (17)
C11'0.107 (2)0.0672 (17)0.108 (2)0.0244 (15)0.0206 (18)0.0285 (16)
C12'0.0956 (19)0.0591 (15)0.0783 (17)0.0123 (13)0.0206 (14)0.0102 (13)
C13'0.0743 (17)0.0603 (14)0.0404 (12)0.0134 (12)0.0018 (11)0.0075 (10)
C14'0.0752 (18)0.0793 (17)0.0652 (15)0.0132 (14)0.0027 (14)0.0144 (13)
C15'0.0742 (18)0.107 (2)0.0759 (18)0.0224 (17)0.0011 (14)0.0211 (16)
C16'0.092 (2)0.097 (2)0.0681 (17)0.0392 (18)0.0093 (16)0.0187 (15)
C17'0.113 (2)0.0684 (16)0.0656 (16)0.0307 (17)0.0097 (16)0.0095 (13)
C18'0.0908 (18)0.0610 (14)0.0540 (14)0.0183 (13)0.0002 (13)0.0041 (11)
F10.068 (4)0.086 (2)0.156 (5)0.020 (3)0.045 (3)0.000 (3)
F20.099 (3)0.155 (5)0.158 (5)0.004 (5)0.021 (4)0.112 (4)
F30.116 (4)0.170 (5)0.156 (5)0.060 (4)0.030 (3)0.076 (4)
F40.180 (6)0.092 (3)0.047 (2)0.012 (4)0.017 (3)0.016 (2)
F50.129 (5)0.105 (4)0.078 (3)0.065 (3)0.007 (3)0.020 (3)
F60.105 (3)0.144 (5)0.101 (4)0.036 (3)0.009 (3)0.041 (4)
F1'0.074 (3)0.221 (11)0.233 (9)0.002 (5)0.028 (5)0.107 (7)
F2'0.225 (9)0.194 (7)0.134 (5)0.024 (6)0.099 (5)0.046 (4)
F3'0.108 (5)0.068 (2)0.248 (8)0.016 (2)0.053 (5)0.040 (4)
F4'0.155 (6)0.276 (9)0.137 (6)0.031 (7)0.074 (5)0.018 (7)
F5'0.288 (10)0.085 (3)0.090 (3)0.029 (5)0.027 (5)0.031 (3)
F6'0.216 (8)0.156 (8)0.093 (4)0.073 (7)0.062 (5)0.018 (4)
O30.0765 (11)0.0503 (9)0.1130 (14)0.0094 (8)0.0291 (10)0.0124 (8)
O40.1081 (16)0.0675 (12)0.228 (3)0.0242 (11)0.0682 (16)0.0529 (14)
O50.1448 (16)0.0514 (9)0.0540 (9)0.0098 (9)0.0162 (10)0.0059 (8)
O60.259 (3)0.0549 (11)0.0727 (12)0.0108 (14)0.0321 (14)0.0074 (9)
C190.088 (2)0.082 (2)0.076 (2)0.0061 (17)0.0180 (17)0.0134 (16)
C200.0713 (17)0.0515 (14)0.0796 (16)0.0078 (13)0.0137 (13)0.0127 (12)
C210.094 (2)0.0736 (18)0.0618 (17)0.0085 (18)0.0177 (16)0.0018 (14)
C220.0926 (19)0.0524 (14)0.0562 (15)0.0042 (13)0.0129 (13)0.0026 (12)
Geometric parameters (Å, º) top
O1—C21.333 (2)C4'—C7'1.509 (3)
O1—C61.407 (2)C4'—H4'0.9800
N3—C21.299 (2)C5'—C6'1.313 (3)
N3—C41.460 (2)C5'—H5'0.9300
N3—H3N0.872 (10)C6'—C13'1.469 (3)
N19—C21.297 (3)C7'—C8'1.362 (3)
N19—H19A0.870 (10)C7'—C12'1.374 (3)
N19—H19B0.880 (10)C8'—C9'1.394 (3)
C4—C51.493 (3)C8'—H8'0.9300
C4—C71.515 (3)C9'—C10'1.354 (4)
C4—H40.9800C9'—H9'0.9300
C5—C61.310 (2)C10'—C11'1.348 (4)
C5—H50.9300C10'—H10'0.9300
C6—C131.470 (3)C11'—C12'1.370 (3)
C7—C81.362 (3)C11'—H11'0.9300
C7—C121.373 (3)C12'—H12'0.9300
C8—C91.389 (3)C13'—C14'1.390 (3)
C8—H80.9300C13'—C18'1.397 (3)
C9—C101.363 (4)C14'—C15'1.388 (3)
C9—H90.9300C14'—H14'0.9300
C10—C111.345 (4)C15'—C16'1.369 (3)
C10—H100.9300C15'—H15'0.9300
C11—C121.381 (3)C16'—C17'1.369 (4)
C11—H110.9300C16'—H16'0.9300
C12—H120.9300C17'—C18'1.395 (3)
C13—C141.385 (3)C17'—H17'0.9300
C13—C181.388 (3)C18'—H18'0.9300
C14—C151.376 (3)F1—C191.309 (3)
C14—H140.9300F2—C191.315 (3)
C15—C161.364 (3)F3—C191.343 (3)
C15—H150.9300F4—C211.315 (3)
C16—C171.373 (3)F5—C211.318 (3)
C16—H160.9300F6—C211.335 (3)
C17—C181.387 (3)F1'—C191.311 (3)
C17—H170.9300F2'—C191.339 (3)
C18—H180.9300F3'—C191.307 (3)
O1'—C2'1.327 (2)F4'—C211.322 (3)
O1'—C6'1.409 (2)F5'—C211.319 (3)
N3'—C2'1.307 (2)F6'—C211.312 (3)
N3'—C4'1.463 (3)O3—C201.227 (2)
N3'—H3'N0.869 (10)O4—C201.216 (2)
N19'—C2'1.296 (3)O5—C221.222 (2)
N19'—H19C0.878 (10)O6—C221.215 (2)
N19'—H19D0.871 (10)C19—C201.492 (3)
C4'—C5'1.489 (3)C21—C221.503 (3)
C2—O1—C6119.49 (15)C12'—C7'—C4'118.96 (19)
C2—N3—C4124.65 (17)C7'—C8'—C9'120.7 (2)
C2—N3—H3N118.1 (13)C7'—C8'—H8'119.7
C4—N3—H3N116.4 (13)C9'—C8'—H8'119.7
C2—N19—H19A118.8 (14)C10'—C9'—C8'120.0 (3)
C2—N19—H19B119.7 (15)C10'—C9'—H9'120.0
H19A—N19—H19B121 (2)C8'—C9'—H9'120.0
N19—C2—N3124.0 (2)C11'—C10'—C9'119.9 (2)
N19—C2—O1114.44 (18)C11'—C10'—H10'120.1
N3—C2—O1121.54 (18)C9'—C10'—H10'120.1
N3—C4—C5108.47 (15)C10'—C11'—C12'120.2 (3)
N3—C4—C7110.95 (16)C10'—C11'—H11'119.9
C5—C4—C7112.88 (16)C12'—C11'—H11'119.9
N3—C4—H4108.1C11'—C12'—C7'121.6 (2)
C5—C4—H4108.1C11'—C12'—H12'119.2
C7—C4—H4108.1C7'—C12'—H12'119.2
C6—C5—C4123.55 (18)C14'—C13'—C18'118.8 (2)
C6—C5—H5118.2C14'—C13'—C6'120.1 (2)
C4—C5—H5118.2C18'—C13'—C6'121.1 (2)
C5—C6—O1119.65 (18)C15'—C14'—C13'120.4 (2)
C5—C6—C13129.71 (19)C15'—C14'—H14'119.8
O1—C6—C13110.61 (16)C13'—C14'—H14'119.8
C8—C7—C12118.5 (2)C16'—C15'—C14'120.5 (3)
C8—C7—C4122.54 (19)C16'—C15'—H15'119.8
C12—C7—C4118.9 (2)C14'—C15'—H15'119.8
C7—C8—C9120.7 (2)C17'—C16'—C15'119.9 (2)
C7—C8—H8119.7C17'—C16'—H16'120.1
C9—C8—H8119.7C15'—C16'—H16'120.1
C10—C9—C8119.9 (3)C16'—C17'—C18'120.8 (3)
C10—C9—H9120.1C16'—C17'—H17'119.6
C8—C9—H9120.1C18'—C17'—H17'119.6
C11—C10—C9119.8 (3)C17'—C18'—C13'119.6 (2)
C11—C10—H10120.1C17'—C18'—H18'120.2
C9—C10—H10120.1C13'—C18'—H18'120.2
C10—C11—C12120.6 (3)F3'—C19—F1127.1 (4)
C10—C11—H11119.7F3'—C19—F1'112.1 (5)
C12—C11—H11119.7F1—C19—F1'40.1 (4)
C7—C12—C11120.5 (3)F3'—C19—F253.1 (3)
C7—C12—H12119.7F1—C19—F2102.0 (5)
C11—C12—H12119.7F1'—C19—F2126.0 (5)
C14—C13—C18118.83 (19)F3'—C19—F2'104.2 (5)
C14—C13—C6120.26 (19)F1—C19—F2'64.2 (4)
C18—C13—C6120.89 (19)F1'—C19—F2'103.7 (5)
C15—C14—C13120.4 (2)F2—C19—F2'51.6 (3)
C15—C14—H14119.8F3'—C19—F356.8 (4)
C13—C14—H14119.8F1—C19—F3102.4 (4)
C16—C15—C14120.8 (2)F1'—C19—F365.5 (4)
C16—C15—H15119.6F2—C19—F3106.4 (4)
C14—C15—H15119.6F2'—C19—F3145.5 (4)
C15—C16—C17119.6 (2)F3'—C19—C20115.7 (3)
C15—C16—H16120.2F1—C19—C20117.2 (3)
C17—C16—H16120.2F1'—C19—C20116.5 (4)
C16—C17—C18120.4 (2)F2—C19—C20115.8 (3)
C16—C17—H17119.8F2'—C19—C20102.6 (3)
C18—C17—H17119.8F3—C19—C20111.6 (3)
C17—C18—C13119.9 (2)O4—C20—O3128.7 (2)
C17—C18—H18120.0O4—C20—C19114.8 (2)
C13—C18—H18120.0O3—C20—C19116.4 (2)
C2'—O1'—C6'119.15 (16)F6'—C21—F440.4 (4)
C2'—N3'—C4'123.66 (19)F6'—C21—F5127.0 (5)
C2'—N3'—H3'N117.6 (14)F4—C21—F5103.0 (4)
C4'—N3'—H3'N117.6 (14)F6'—C21—F5'108.1 (5)
C2'—N19'—H19C120.4 (17)F4—C21—F5'129.8 (4)
C2'—N19'—H19D122.1 (15)F5—C21—F5'61.7 (4)
H19C—N19'—H19D117 (2)F6'—C21—F4'103.6 (5)
N19'—C2'—N3'123.8 (2)F4—C21—F4'65.5 (4)
N19'—C2'—O1'114.67 (19)F5—C21—F4'45.4 (4)
N3'—C2'—O1'121.5 (2)F5'—C21—F4'105.4 (5)
N3'—C4'—C5'108.01 (16)F6'—C21—F666.7 (4)
N3'—C4'—C7'111.93 (16)F4—C21—F6104.4 (4)
C5'—C4'—C7'113.05 (17)F5—C21—F6106.8 (4)
N3'—C4'—H4'107.9F5'—C21—F648.7 (4)
C5'—C4'—H4'107.9F4'—C21—F6138.9 (4)
C7'—C4'—H4'107.9F6'—C21—C22116.4 (4)
C6'—C5'—C4'123.3 (2)F4—C21—C22114.6 (3)
C6'—C5'—H5'118.3F5—C21—C22114.2 (3)
C4'—C5'—H5'118.3F5'—C21—C22115.1 (3)
C5'—C6'—O1'119.43 (19)F4'—C21—C22107.1 (4)
C5'—C6'—C13'130.1 (2)F6—C21—C22112.9 (3)
O1'—C6'—C13'110.44 (18)O6—C22—O5128.4 (2)
C8'—C7'—C12'117.7 (2)O6—C22—C21115.6 (2)
C8'—C7'—C4'123.34 (19)O5—C22—C21116.0 (2)
C4—N3—C2—N19171.3 (2)N3'—C4'—C7'—C8'35.2 (3)
C4—N3—C2—O17.3 (3)C5'—C4'—C7'—C8'87.1 (3)
C6—O1—C2—N19173.68 (19)N3'—C4'—C7'—C12'147.3 (2)
C6—O1—C2—N37.6 (3)C5'—C4'—C7'—C12'90.4 (2)
C2—N3—C4—C516.9 (3)C12'—C7'—C8'—C9'0.6 (4)
C2—N3—C4—C7141.4 (2)C4'—C7'—C8'—C9'176.9 (2)
N3—C4—C5—C613.7 (3)C7'—C8'—C9'—C10'0.0 (4)
C7—C4—C5—C6137.1 (2)C8'—C9'—C10'—C11'0.1 (5)
C4—C5—C6—O11.6 (3)C9'—C10'—C11'—C12'1.0 (4)
C4—C5—C6—C13176.09 (19)C10'—C11'—C12'—C7'1.7 (4)
C2—O1—C6—C510.2 (3)C8'—C7'—C12'—C11'1.5 (4)
C2—O1—C6—C13171.68 (17)C4'—C7'—C12'—C11'176.1 (2)
N3—C4—C7—C833.2 (3)C5'—C6'—C13'—C14'9.2 (3)
C5—C4—C7—C888.8 (2)O1'—C6'—C13'—C14'168.68 (18)
N3—C4—C7—C12148.11 (19)C5'—C6'—C13'—C18'171.4 (2)
C5—C4—C7—C1289.9 (2)O1'—C6'—C13'—C18'10.7 (3)
C12—C7—C8—C90.1 (3)C18'—C13'—C14'—C15'0.6 (3)
C4—C7—C8—C9178.6 (2)C6'—C13'—C14'—C15'178.9 (2)
C7—C8—C9—C100.2 (4)C13'—C14'—C15'—C16'0.4 (4)
C8—C9—C10—C110.5 (4)C14'—C15'—C16'—C17'0.8 (4)
C9—C10—C11—C121.4 (5)C15'—C16'—C17'—C18'0.3 (4)
C8—C7—C12—C111.1 (3)C16'—C17'—C18'—C13'0.7 (3)
C4—C7—C12—C11177.7 (2)C14'—C13'—C18'—C17'1.1 (3)
C10—C11—C12—C71.7 (4)C6'—C13'—C18'—C17'178.36 (19)
C5—C6—C13—C1410.8 (3)F3'—C19—C20—O4164.6 (7)
O1—C6—C13—C14167.00 (18)F1—C19—C20—O415.4 (6)
C5—C6—C13—C18170.9 (2)F1'—C19—C20—O429.7 (8)
O1—C6—C13—C1811.2 (3)F2—C19—C20—O4135.9 (7)
C18—C13—C14—C150.6 (3)F2'—C19—C20—O482.7 (6)
C6—C13—C14—C15177.7 (2)F3—C19—C20—O4102.2 (7)
C13—C14—C15—C160.2 (4)F3'—C19—C20—O314.4 (8)
C14—C15—C16—C170.0 (4)F1—C19—C20—O3165.6 (5)
C15—C16—C17—C180.1 (4)F1'—C19—C20—O3149.2 (8)
C16—C17—C18—C130.5 (3)F2—C19—C20—O345.1 (7)
C14—C13—C18—C170.7 (3)F2'—C19—C20—O398.3 (5)
C6—C13—C18—C17177.5 (2)F3—C19—C20—O376.8 (7)
C4'—N3'—C2'—N19'168.2 (2)F6'—C21—C22—O632.2 (8)
C4'—N3'—C2'—O1'11.5 (3)F4—C21—C22—O612.8 (6)
C6'—O1'—C2'—N19'171.29 (18)F5—C21—C22—O6131.2 (6)
C6'—O1'—C2'—N3'9.0 (3)F5'—C21—C22—O6160.1 (8)
C2'—N3'—C4'—C5'23.4 (3)F4'—C21—C22—O683.1 (7)
C2'—N3'—C4'—C7'148.5 (2)F6—C21—C22—O6106.5 (6)
N3'—C4'—C5'—C6'17.7 (3)F6'—C21—C22—O5147.9 (7)
C7'—C4'—C5'—C6'142.1 (2)F4—C21—C22—O5167.1 (5)
C4'—C5'—C6'—O1'0.7 (3)F5—C21—C22—O548.7 (6)
C4'—C5'—C6'—C13'177.01 (19)F5'—C21—C22—O519.9 (8)
C2'—O1'—C6'—C5'14.2 (3)F4'—C21—C22—O596.8 (7)
C2'—O1'—C6'—C13'167.65 (17)F6—C21—C22—O573.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O50.87 (1)1.90 (1)2.772 (2)178 (2)
N19—H19A···O30.87 (1)1.95 (1)2.823 (2)179 (2)
N19—H19B···O60.88 (1)1.90 (1)2.778 (3)173 (2)
N3—H3N···O3i0.87 (1)1.90 (1)2.766 (2)177 (2)
N19—H19D···O4i0.87 (1)1.90 (1)2.770 (3)174 (2)
N19—H19C···O50.88 (1)1.95 (1)2.820 (2)174 (2)
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H15N2O+·C2F3O2
Mr364.32
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.341 (2), 11.867 (2), 14.409 (3)
α, β, γ (°)90.62 (2), 92.68 (2), 91.03 (2)
V3)1765.9 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.58 × 0.50 × 0.42
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7215, 6591, 3495
Rint0.012
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 0.94
No. of reflections6591
No. of parameters548
No. of restraints18
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.18

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL/PC (Siemens, 1991), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC.

Selected geometric parameters (Å, º) top
O1—C21.333 (2)N3'—C2'1.307 (2)
O1—C61.407 (2)N3'—C4'1.463 (3)
N3—C21.299 (2)N19'—C2'1.296 (3)
N3—C41.460 (2)O3—C201.227 (2)
N19—C21.297 (3)O4—C201.216 (2)
O1'—C2'1.327 (2)O5—C221.222 (2)
O1'—C6'1.409 (2)O6—C221.215 (2)
C2—O1—C6119.49 (15)C2'—O1'—C6'119.15 (16)
C2—N3—C4124.65 (17)C2'—N3'—C4'123.66 (19)
N19—C2—N3124.0 (2)N19'—C2'—N3'123.8 (2)
N19—C2—O1114.44 (18)N19'—C2'—O1'114.67 (19)
N3—C2—O1121.54 (18)N3'—C2'—O1'121.5 (2)
C4—N3—C2—N19171.3 (2)C4'—N3'—C2'—N19'168.2 (2)
C4—N3—C2—O17.3 (3)C4'—N3'—C2'—O1'11.5 (3)
C4—C5—C6—O11.6 (3)C4'—C5'—C6'—O1'0.7 (3)
N3—C4—C7—C833.2 (3)N3'—C4'—C7'—C8'35.2 (3)
O1—C6—C13—C1811.2 (3)O1'—C6'—C13'—C18'10.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O50.87 (1)1.90 (1)2.772 (2)178 (2)
N19—H19A···O30.87 (1)1.95 (1)2.823 (2)179 (2)
N19—H19B···O60.88 (1)1.90 (1)2.778 (3)173 (2)
N3'—H3'N···O3i0.87 (1)1.90 (1)2.766 (2)177 (2)
N19'—H19D···O4i0.87 (1)1.90 (1)2.770 (3)174 (2)
N19'—H19C···O50.88 (1)1.95 (1)2.820 (2)174 (2)
Symmetry code: (i) x, y+1, z.
 

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