1-Oxo-3-phenyl-1,2-dihydro­pyrido[1,2-a]pyrazin-5-ium hexa­fluoro­phosphate

In the structure of the title compound, C₁₄H₁₁N₂O⁺·PF₆^-, all the bond lengths and angles have normal values. The pyrido[1,2-a]pyrazinium system and the phenyl ring are conjugated. In the crystal structure, the phenyl­pyrido[1,2-a]pyrazinium rings are arranged in parallel layers.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.067
• wR factor = 0.231
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   P1     -   F1      ..       5.07 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   P1     -   F2      ..       6.26 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   P1     -   F3      ..       6.17 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   P1     -   F5      ..       6.97 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT432_ALERT_2_C Short Inter X...Y Contact  F4     ..  C7      ..       2.90 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H11 N2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   6 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 193
              ^13^C NMR (300 MHz, DMSO-d~6~)~ \d: 155.7, 142.4, 139.0, 138.2, 131.9, 130.4,
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-Oxo-3-phenyl-1,2-dihydropyrido[1,2-a]pyrazin-5-ium hexafluorophosphate

Crystal data

C14H11N2O^+·PF6^−	Z = 2
Mr = 368.22	F(000) = 372
Triclinic, P1	Dx = 1.637 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.036 (2) Å	Cell parameters from 25 reflections
b = 8.724 (2) Å	θ = 10.8–14.3°
c = 11.881 (2) Å	µ = 0.26 mm^−1
α = 91.13 (2)°	T = 295 K
β = 109.52 (2)°	Prism, colorless
γ = 106.38 (2)°	0.25 × 0.25 × 0.15 mm
V = 747.2 (3) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1580 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 25.2°, θmin = 1.8°
ω/2θ scans	h = −1→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.939, Tmax = 0.963	l = −14→13
3315 measured reflections	3 standard reflections every 3600 min
2693 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.231	w = 1/[σ^2(Fo^2) + (0.1102P)^2 + 1.1617P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2693 reflections	Δρmax = 0.68 e Å^−3
218 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (4)

Special details

Experimental. ¹³C NMR (300 MHz, DMSO-d₆) δ: 155.7, 142.4, 139.0, 138.2, 131.9, 130.4, 129.7, 127.7, 126.7, 110.5.

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 (Ų)

	x	y	z	Uiso*/Ueq
P1	0.49980 (10)	0.75296 (9)	0.66184 (7)	0.0573 (2)
F1	0.6383 (3)	0.6646 (3)	0.6465 (2)	0.1383 (9)
F2	0.3418 (4)	0.6379 (3)	0.5503 (2)	0.1244 (11)
F3	0.4616 (4)	0.6298 (3)	0.7487 (2)	0.1349 (10)
F4	0.3604 (3)	0.8407 (3)	0.6708 (2)	0.1385 (9)
F5	0.5438 (4)	0.8652 (3)	0.5664 (2)	0.1382 (11)
F6	0.6613 (3)	0.8736 (3)	0.7645 (2)	0.1260 (11)
O1	−0.2855 (2)	1.0228 (2)	0.09445 (16)	0.0618 (6)
N1	−0.3228 (2)	0.7780 (2)	0.32553 (16)	0.0397 (5)
N2	−0.5408 (2)	0.8600 (2)	0.12084 (17)	0.0434 (5)
H2	−0.6116	0.8792	0.0540	0.052*
C1	−0.0478 (3)	0.9296 (3)	0.2960 (2)	0.0500 (7)
H1	0.0098	1.0009	0.2533	0.060*
C2	0.0569 (4)	0.8744 (3)	0.3933 (3)	0.0580 (8)
H2A	0.1853	0.9051	0.4157	0.070*
C3	−0.0310 (3)	0.7726 (3)	0.4576 (2)	0.0567 (8)
H3	0.0388	0.7360	0.5248	0.068*
C4	−0.2179 (3)	0.7257 (3)	0.4235 (2)	0.0514 (8)
H4	−0.2756	0.6570	0.4674	0.062*
C5	−0.5162 (3)	0.7244 (3)	0.2907 (2)	0.0444 (7)
H5	−0.5706	0.6620	0.3391	0.053*
C6	−0.6232 (3)	0.7610 (3)	0.1899 (2)	0.0398 (6)
C7	−0.3561 (3)	0.9277 (3)	0.1527 (2)	0.0442 (7)
C8	−0.2380 (3)	0.8798 (3)	0.2614 (2)	0.0408 (6)
C9	−0.8287 (3)	0.6990 (3)	0.1481 (2)	0.0446 (7)
C10	−0.9139 (4)	0.5623 (4)	0.1895 (3)	0.0652 (9)
H10	−0.8418	0.5094	0.2427	0.078*
C11	−1.1029 (4)	0.5045 (4)	0.1530 (3)	0.0791 (11)
H11	−1.1579	0.4138	0.1828	0.095*
C12	−1.2113 (4)	0.5775 (4)	0.0737 (3)	0.0766 (11)
H12	−1.3397	0.5376	0.0500	0.092*
C13	−1.1314 (4)	0.7097 (4)	0.0290 (3)	0.0730 (10)
H13	−1.2060	0.7573	−0.0275	0.088*
C14	−0.9387 (3)	0.7742 (4)	0.0672 (2)	0.0572 (8)
H14	−0.8848	0.8667	0.0387	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0489 (3)	0.0542 (4)	0.0657 (4)	0.0157 (3)	0.0161 (3)	0.0127 (3)
F1	0.1566 (13)	0.1739 (16)	0.1608 (18)	0.1183 (12)	0.0932 (12)	0.0695 (14)
F2	0.1304 (18)	0.0836 (13)	0.1138 (18)	0.0258 (13)	−0.0062 (15)	−0.0209 (13)
F3	0.1338 (16)	0.1516 (19)	0.1174 (14)	0.0138 (16)	0.0642 (12)	0.0617 (14)
F4	0.0847 (10)	0.1804 (17)	0.1365 (18)	0.0804 (11)	−0.0073 (12)	−0.0579 (14)
F5	0.150 (2)	0.1180 (15)	0.1327 (17)	0.0294 (15)	0.0397 (15)	0.0735 (13)
F6	0.0773 (13)	0.1117 (16)	0.1315 (19)	0.0195 (12)	−0.0254 (14)	−0.0184 (15)
O1	0.0470 (8)	0.0855 (11)	0.0589 (9)	0.0211 (8)	0.0240 (7)	0.0386 (8)
N1	0.0387 (8)	0.0427 (9)	0.0374 (9)	0.0127 (8)	0.0123 (7)	0.0120 (8)
N2	0.0353 (8)	0.0557 (10)	0.0410 (9)	0.0171 (8)	0.0124 (7)	0.0166 (8)
C1	0.0424 (11)	0.0568 (14)	0.0529 (13)	0.0143 (10)	0.0198 (9)	0.0116 (11)
C2	0.0412 (12)	0.0666 (16)	0.0602 (15)	0.0175 (11)	0.0097 (11)	0.0033 (13)
C3	0.0491 (13)	0.0672 (15)	0.0486 (14)	0.0221 (12)	0.0068 (11)	0.0146 (12)
C4	0.0520 (12)	0.0533 (13)	0.0446 (12)	0.0177 (11)	0.0100 (10)	0.0166 (11)
C5	0.0387 (10)	0.0489 (12)	0.0475 (11)	0.0110 (9)	0.0194 (9)	0.0142 (10)
C6	0.0381 (9)	0.0442 (11)	0.0424 (11)	0.0142 (9)	0.0192 (8)	0.0098 (9)
C7	0.0417 (10)	0.0560 (12)	0.0408 (11)	0.0178 (10)	0.0189 (8)	0.0155 (10)
C8	0.0409 (10)	0.0452 (11)	0.0402 (11)	0.0163 (9)	0.0165 (8)	0.0084 (9)
C9	0.0383 (10)	0.0549 (13)	0.0437 (11)	0.0149 (10)	0.0180 (8)	0.0032 (10)
C10	0.0457 (13)	0.0659 (16)	0.0809 (18)	0.0134 (12)	0.0209 (12)	0.0208 (14)
C11	0.0514 (14)	0.0695 (19)	0.110 (2)	0.0011 (14)	0.0351 (14)	0.0091 (18)
C12	0.0372 (13)	0.092 (2)	0.086 (2)	0.0046 (15)	0.0174 (13)	−0.0165 (18)
C13	0.0472 (12)	0.115 (2)	0.0562 (16)	0.0346 (14)	0.0102 (12)	0.0025 (16)
C14	0.0402 (11)	0.0826 (17)	0.0500 (13)	0.0218 (12)	0.0145 (10)	0.0134 (13)

Geometric parameters (Å, º)

P1—F3	1.544 (3)	C3—C4	1.352 (4)
P1—F6	1.549 (2)	C3—H3	0.9300
P1—F4	1.554 (3)	C4—H4	0.9300
P1—F1	1.575 (3)	C5—C6	1.326 (3)
P1—F2	1.575 (2)	C5—H5	0.9300
P1—F5	1.577 (3)	C6—C9	1.484 (3)
O1—C7	1.228 (3)	C7—C8	1.473 (3)
N1—C4	1.362 (3)	C9—C10	1.386 (4)
N1—C8	1.366 (3)	C9—C14	1.386 (4)
N1—C5	1.399 (3)	C10—C11	1.367 (4)
N2—C7	1.348 (3)	C10—H10	0.9300
N2—C6	1.387 (3)	C11—C12	1.357 (5)
N2—H2	0.8600	C11—H11	0.9300
C1—C2	1.370 (4)	C12—C13	1.363 (5)
C1—C8	1.376 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.396 (4)
C2—C3	1.381 (4)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14	0.9300
F3—P1—F6	92.48 (15)	N1—C4—H4	119.6
F3—P1—F4	96.17 (17)	C6—C5—N1	121.2 (2)
F6—P1—F4	91.81 (14)	C6—C5—H5	119.4
F3—P1—F1	85.79 (17)	N1—C5—H5	119.4
F6—P1—F1	89.75 (15)	C5—C6—N2	119.0 (2)
F4—P1—F1	177.44 (16)	C5—C6—C9	122.1 (2)
F3—P1—F2	91.83 (14)	N2—C6—C9	118.87 (19)
F6—P1—F2	175.49 (17)	O1—C7—N2	123.0 (2)
F4—P1—F2	89.04 (14)	O1—C7—C8	120.2 (2)
F1—P1—F2	89.24 (15)	N2—C7—C8	116.8 (2)
F3—P1—F5	174.08 (18)	N1—C8—C1	120.1 (2)
F6—P1—F5	90.22 (15)	N1—C8—C7	118.08 (19)
F4—P1—F5	89.00 (17)	C1—C8—C7	121.8 (2)
F1—P1—F5	88.96 (17)	C10—C9—C14	118.8 (2)
F2—P1—F5	85.37 (14)	C10—C9—C6	119.9 (2)
C4—N1—C8	119.6 (2)	C14—C9—C6	121.4 (2)
C4—N1—C5	119.5 (2)	C11—C10—C9	120.6 (3)
C8—N1—C5	120.89 (19)	C11—C10—H10	119.7
C7—N2—C6	123.69 (19)	C9—C10—H10	119.7
C7—N2—H2	118.2	C12—C11—C10	120.8 (3)
C6—N2—H2	118.2	C12—C11—H11	119.6
C2—C1—C8	120.1 (3)	C10—C11—H11	119.6
C2—C1—H1	120.0	C11—C12—C13	119.8 (3)
C8—C1—H1	120.0	C11—C12—H12	120.1
C1—C2—C3	119.0 (2)	C13—C12—H12	120.1
C1—C2—H2A	120.5	C12—C13—C14	120.6 (3)
C3—C2—H2A	120.5	C12—C13—H13	119.7
C4—C3—C2	120.4 (2)	C14—C13—H13	119.7
C4—C3—H3	119.8	C9—C14—C13	119.2 (3)
C2—C3—H3	119.8	C9—C14—H14	120.4
C3—C4—N1	120.8 (2)	C13—C14—H14	120.4
C3—C4—H4	119.6
C8—C1—C2—C3	−2.0 (4)	C2—C1—C8—C7	−175.9 (3)
C1—C2—C3—C4	1.3 (4)	O1—C7—C8—N1	177.8 (2)
C2—C3—C4—N1	−0.1 (4)	N2—C7—C8—N1	−3.5 (3)
C8—N1—C4—C3	−0.4 (4)	O1—C7—C8—C1	−4.8 (4)
C5—N1—C4—C3	178.5 (3)	N2—C7—C8—C1	173.9 (2)
C4—N1—C5—C6	−173.9 (2)	C5—C6—C9—C10	−21.2 (4)
C8—N1—C5—C6	5.0 (4)	N2—C6—C9—C10	158.5 (3)
N1—C5—C6—N2	−2.8 (4)	C5—C6—C9—C14	159.3 (3)
N1—C5—C6—C9	176.9 (2)	N2—C6—C9—C14	−20.9 (4)
C7—N2—C6—C5	−2.8 (4)	C14—C9—C10—C11	−1.2 (5)
C7—N2—C6—C9	177.4 (2)	C6—C9—C10—C11	179.3 (3)
C6—N2—C7—O1	−175.4 (2)	C9—C10—C11—C12	1.3 (6)
C6—N2—C7—C8	5.9 (4)	C10—C11—C12—C13	0.5 (6)
C4—N1—C8—C1	−0.3 (4)	C11—C12—C13—C14	−2.3 (5)
C5—N1—C8—C1	−179.2 (2)	C10—C9—C14—C13	−0.6 (4)
C4—N1—C8—C7	177.1 (2)	C6—C9—C14—C13	178.9 (3)
C5—N1—C8—C7	−1.7 (3)	C12—C13—C14—C9	2.3 (5)
C2—C1—C8—N1	1.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	2.00	2.838 (6)	164

Symmetry code: (i) −x+1, −y+2, −z.