organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-6,7,8,9-tetra­hydro-4H-pyrido[1,2-a]pyrimidin-3-yl)eth­yl]piperidinium nitrate

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and bCollege of Pharmacy, Jiangsu University, Zhenjiang 212013, People's Republic of China
*Correspondence e-mail: whsunyu@163.com

(Received 31 March 2009; accepted 10 June 2009; online 20 June 2009)

In the risperidone cation of the title compound, C23H28FN4O2+·NO3, the piperidine ring adopts a chair conformation and the tetra­hydro­pyridine ring is disordered over two orientations in a 0.620 (11):0.380 (11) ratio. N—H⋯O, C—H⋯O and C—H⋯F hydrogen bonds are present in the crystal structure.

Related literature

Risperidone is an anti­psychotic agent belonging to a new chemical class of benzisoxazole derivatives, see: Callaghan et al. (1999[Callaghan, J. T., Bergstrom, R. F., Ptak, L. R. & Beasley, C. M. (1999). Clin. Pharm. 37, 177-193.]); Tandon (2002[Tandon, R. (2002). Psychiatr. Q. 73, 297-311.]).

[Scheme 1]

Experimental

Crystal data
  • C23H28FN4O2+·NO3

  • Mr = 473.50

  • Monoclinic, P 21 /c

  • a = 8.1655 (16) Å

  • b = 21.866 (4) Å

  • c = 12.635 (3) Å

  • β = 91.94 (3)°

  • V = 2254.6 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 (2) K

  • 0.15 × 0.12 × 0.09 mm

Data collection
  • Rigaku Scxmini 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) Tmin = 0.94, Tmax = 0.99

  • 22497 measured reflections

  • 5164 independent reflections

  • 3386 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.176

  • S = 1.04

  • 5164 reflections

  • 325 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2B⋯O3i 0.89 (3) 2.07 (3) 2.866 (3) 149 (2)
N2—H2B⋯O5i 0.89 (3) 2.33 (3) 3.157 (5) 156 (2)
C2—H2A⋯O2ii 0.93 2.19 3.107 (3) 171
C10—H10A⋯O4 0.97 2.50 3.221 (4) 131
C13—H13B⋯Fiii 0.97 2.33 3.264 (3) 161
Symmetry codes: (i) x+1, y, z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Risperidone is an antipsychotic agent belonging to a new chemical class of benzisoxazole derivatives, available worldwide since the early 1990s (Callaghan et al., 1999; Tandon, 2002). We report here the synthesis and crystal structure of the title complex, (I) (Fig. 1).

In the structure of (I), there is one risperidone cation and one NO3- anion in the asymmetric unit. The expected proton transfer from nitric acid to risperidone occurs at atom N2 of the piperidine ring. Consequently, atom N2 shows quaternary character and bears a positive charge. Compound (I) contains a piperidine ring, one end of which is connected to a pyridopyrimidine group via an ethyl bridge, while the other end is connected to an almost-planar fluorobenzisoxazole ring system. In the crystal structure of the title compound, an elaborate hydrogen-bond network is formed. Each NO3-, one amino group and one carbonyl group in the risperidone molecule are involved in the hydrogen-bond network (Table 1, Fig. 2).

Related literature top

Risperidone is an antipsychotic agent belonging to a new chemical class of benzisoxazole derivatives, see: Callaghan et al. (1999); Tandon (2002).

Experimental top

All of the reagents and solvents were purchased from either Aldrich and used without further purification. The compound was recrystallized from a solution in a mixture of methanol and water, with the pH adjusted to 5–6 using 0.1 mol/l HNO3, giving colourless crystals of (I) suitable for X-ray diffraction.

Refinement top

The H2B was refined isotropically. H atoms bound to carbon were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.96 Å for methyl and 0.97 Å for others, Uiso(H)=1.2Ueq(C). The C19 and C20 atoms are disordered over two sites with refined occupancies of 0.620 (11) and 0.380 (11).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of the compound (I). Hydrogen bonds are shown as dashed lines (Symmetry codes: (i) x, -y + 1/2, z - 1/2; (ii) -x + 1, y - 1/2, -z + 3/2).
4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-6,7,8,9-tetrahydro- 4H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidinium nitrate top
Crystal data top
C23H28FN4O2+·NO3F(000) = 1000
Mr = 473.50Dx = 1.395 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4798 reflections
a = 8.1655 (16) Åθ = 3.1–25.0°
b = 21.866 (4) ŵ = 0.11 mm1
c = 12.635 (3) ÅT = 293 K
β = 91.94 (3)°Block, colourless
V = 2254.6 (8) Å30.15 × 0.12 × 0.09 mm
Z = 4
Data collection top
Rigaku Scxmini 1K CCD area-detector
diffractometer
5164 independent reflections
Radiation source: fine-focus sealed tube3386 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 8.192 pixels mm-1θmax = 27.5°, θmin = 3.1°
Thin–slice ω scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 2828
Tmin = 0.94, Tmax = 0.99l = 1616
22497 measured 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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.07P)2 + 1.3338P]
where P = (Fo2 + 2Fc2)/3
5164 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C23H28FN4O2+·NO3V = 2254.6 (8) Å3
Mr = 473.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1655 (16) ŵ = 0.11 mm1
b = 21.866 (4) ÅT = 293 K
c = 12.635 (3) Å0.15 × 0.12 × 0.09 mm
β = 91.94 (3)°
Data collection top
Rigaku Scxmini 1K CCD area-detector
diffractometer
5164 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
3386 reflections with I > 2σ(I)
Tmin = 0.94, Tmax = 0.99Rint = 0.047
22497 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.32 e Å3
5164 reflectionsΔρmin = 0.28 e Å3
325 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)
F0.5593 (2)0.48655 (7)0.71974 (17)0.0788 (6)
C10.6901 (3)0.35617 (11)0.57834 (19)0.0394 (6)
C20.6642 (3)0.41746 (11)0.5995 (2)0.0504 (7)
H2A0.69860.44880.55570.060*
C30.5836 (3)0.42758 (11)0.6905 (2)0.0511 (7)
C40.5266 (3)0.38241 (12)0.7573 (2)0.0513 (7)
H4A0.46910.39280.81700.062*
C50.5565 (3)0.32220 (11)0.7336 (2)0.0438 (6)
H5A0.52060.29110.77730.053*
C60.6420 (3)0.30878 (10)0.64249 (18)0.0358 (5)
C70.6994 (3)0.25504 (10)0.59070 (17)0.0353 (5)
C80.6892 (3)0.19000 (10)0.62775 (18)0.0369 (5)
H8A0.57770.18260.65120.044*
C90.7256 (3)0.14414 (11)0.54190 (19)0.0454 (6)
H9A0.64760.14950.48300.055*
H9B0.83430.15180.51620.055*
C100.7164 (3)0.07913 (11)0.5818 (2)0.0477 (6)
H10A0.60550.07050.60260.057*
H10B0.74270.05120.52520.057*
C110.8011 (4)0.11368 (11)0.75999 (19)0.0488 (7)
H11A0.88220.10800.81700.059*
H11B0.69400.10590.78800.059*
C120.8082 (4)0.17918 (11)0.72137 (19)0.0470 (6)
H12A0.91870.18840.70050.056*
H12B0.78160.20650.77870.056*
C130.8196 (3)0.00410 (10)0.7117 (2)0.0403 (6)
H13A0.81320.02270.65050.048*
H13B0.71860.00050.74910.048*
C140.9607 (3)0.01635 (11)0.7837 (2)0.0427 (6)
H14A1.05950.02000.74360.051*
H14B0.98040.01350.83940.051*
C150.9184 (3)0.07729 (10)0.83123 (18)0.0361 (5)
C160.8370 (3)0.07566 (11)0.9298 (2)0.0418 (6)
C210.8352 (3)0.18542 (10)0.92195 (18)0.0370 (5)
C220.9444 (3)0.13241 (10)0.78520 (17)0.0360 (5)
C231.0216 (3)0.13858 (13)0.6798 (2)0.0506 (7)
H23A1.04770.09870.65330.076*
H23B0.94650.15860.63100.076*
H23C1.12000.16240.68760.076*
O10.7678 (2)0.33351 (8)0.49358 (13)0.0507 (5)
O20.7981 (3)0.02875 (9)0.97639 (17)0.0684 (6)
O30.1111 (3)0.05259 (15)0.5454 (2)0.0993 (9)
O40.3344 (3)0.09708 (14)0.5171 (2)0.1005 (9)
O50.1993 (6)0.11232 (14)0.6583 (2)0.1389 (15)
N10.7710 (3)0.26831 (9)0.50384 (16)0.0449 (5)
N20.8321 (2)0.06899 (8)0.67408 (14)0.0329 (4)
N30.9023 (2)0.18672 (8)0.83033 (15)0.0393 (5)
N40.8013 (2)0.13271 (9)0.97382 (15)0.0384 (5)
N50.2204 (3)0.08745 (11)0.5749 (2)0.0557 (6)
C170.7250 (4)0.13102 (14)1.0785 (2)0.0573 (7)0.620 (11)
H17A0.60950.12111.06970.069*
H17B0.77710.09981.12250.069*
C200.7977 (4)0.24588 (12)0.9722 (2)0.0546 (7)0.620 (11)
C180.7463 (10)0.1965 (3)1.1339 (4)0.0565 (17)0.620 (11)
H18A0.86050.20241.15510.068*0.620 (11)
H18B0.68240.19751.19720.068*0.620 (11)
C190.6928 (8)0.2473 (2)1.0624 (4)0.0495 (15)0.620 (11)
H19A0.70330.28621.09880.059*0.620 (11)
H19B0.57920.24181.03940.059*0.620 (11)
C17'0.7250 (4)0.13102 (14)1.0785 (2)0.0573 (7)0.380 (11)
C20'0.7977 (4)0.24588 (12)0.9722 (2)0.0546 (7)0.380 (11)
H20B0.88830.27390.96320.066*
H20C0.70040.26350.93830.066*
C18'0.6516 (13)0.1831 (4)1.1149 (6)0.053 (3)0.380 (11)
H18C0.54750.18991.07740.063*0.380 (11)
H18D0.63210.17961.18990.063*0.380 (11)
C19'0.7689 (15)0.2360 (4)1.0947 (8)0.053 (2)*0.380 (11)
H19C0.72470.27321.12410.064*0.380 (11)
H19D0.87330.22781.13090.064*0.380 (11)
H2B0.933 (4)0.0742 (12)0.652 (2)0.052 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.0694 (11)0.0375 (9)0.1310 (17)0.0082 (8)0.0251 (11)0.0069 (10)
C10.0371 (12)0.0404 (13)0.0408 (13)0.0004 (10)0.0023 (10)0.0123 (10)
C20.0442 (14)0.0364 (14)0.0706 (18)0.0022 (11)0.0040 (13)0.0174 (13)
C30.0389 (14)0.0346 (13)0.080 (2)0.0061 (11)0.0035 (14)0.0016 (13)
C40.0455 (15)0.0489 (16)0.0600 (16)0.0073 (12)0.0120 (13)0.0012 (13)
C50.0448 (14)0.0399 (13)0.0471 (14)0.0016 (11)0.0101 (11)0.0085 (11)
C60.0352 (12)0.0332 (12)0.0388 (12)0.0008 (9)0.0006 (10)0.0076 (9)
C70.0370 (12)0.0379 (12)0.0307 (11)0.0013 (10)0.0001 (10)0.0045 (9)
C80.0397 (12)0.0337 (12)0.0378 (12)0.0002 (10)0.0068 (10)0.0038 (9)
C90.0618 (16)0.0418 (14)0.0320 (12)0.0057 (12)0.0085 (11)0.0004 (10)
C100.0566 (16)0.0386 (13)0.0468 (14)0.0020 (12)0.0156 (12)0.0048 (11)
C110.0818 (19)0.0333 (13)0.0314 (12)0.0025 (13)0.0038 (12)0.0013 (10)
C120.0786 (18)0.0301 (12)0.0318 (12)0.0001 (12)0.0053 (12)0.0015 (9)
C130.0447 (13)0.0273 (11)0.0490 (14)0.0032 (10)0.0016 (11)0.0038 (10)
C140.0419 (13)0.0347 (13)0.0514 (14)0.0029 (10)0.0015 (11)0.0070 (11)
C150.0369 (12)0.0330 (12)0.0383 (12)0.0000 (9)0.0005 (10)0.0036 (9)
C160.0482 (14)0.0325 (12)0.0448 (14)0.0031 (11)0.0025 (11)0.0054 (10)
C210.0395 (12)0.0313 (12)0.0401 (13)0.0005 (10)0.0005 (10)0.0023 (10)
C220.0383 (12)0.0368 (12)0.0331 (11)0.0021 (10)0.0018 (10)0.0016 (9)
C230.0577 (16)0.0554 (16)0.0393 (13)0.0001 (13)0.0108 (12)0.0011 (12)
O10.0646 (12)0.0439 (10)0.0444 (10)0.0006 (9)0.0128 (9)0.0158 (8)
O20.0969 (16)0.0391 (11)0.0707 (13)0.0065 (10)0.0239 (12)0.0170 (9)
O30.0716 (16)0.146 (3)0.0805 (17)0.0343 (17)0.0118 (14)0.0153 (17)
O40.0505 (13)0.125 (2)0.128 (2)0.0108 (14)0.0254 (15)0.0176 (18)
O50.264 (5)0.081 (2)0.0734 (18)0.020 (2)0.026 (2)0.0229 (16)
N10.0574 (13)0.0401 (11)0.0376 (11)0.0001 (10)0.0068 (10)0.0080 (9)
N20.0332 (10)0.0319 (10)0.0337 (10)0.0011 (8)0.0028 (8)0.0032 (8)
N30.0485 (11)0.0291 (10)0.0407 (11)0.0036 (8)0.0074 (9)0.0009 (8)
N40.0454 (11)0.0381 (11)0.0321 (10)0.0019 (9)0.0048 (8)0.0014 (8)
N50.0583 (15)0.0554 (15)0.0532 (14)0.0023 (12)0.0000 (12)0.0049 (12)
C170.0660 (18)0.072 (2)0.0350 (13)0.0093 (15)0.0143 (13)0.0094 (13)
C200.0621 (17)0.0377 (14)0.0647 (18)0.0015 (12)0.0104 (14)0.0125 (12)
C180.072 (4)0.064 (4)0.033 (2)0.007 (3)0.004 (3)0.010 (2)
C190.052 (3)0.049 (3)0.047 (3)0.009 (2)0.003 (2)0.011 (2)
C17'0.0660 (18)0.072 (2)0.0350 (13)0.0093 (15)0.0143 (13)0.0094 (13)
C20'0.0621 (17)0.0377 (14)0.0647 (18)0.0015 (12)0.0104 (14)0.0125 (12)
C18'0.051 (6)0.064 (5)0.042 (4)0.004 (4)0.008 (4)0.017 (4)
Geometric parameters (Å, º) top
F—C31.358 (3)C14—H14A0.9700
C1—O11.357 (3)C14—H14B0.9700
C1—C61.381 (3)C15—C221.358 (3)
C1—C21.384 (3)C15—C161.432 (3)
C2—C31.362 (4)C16—O21.230 (3)
C2—H2A0.9300C16—N41.400 (3)
C3—C41.390 (4)C21—N31.298 (3)
C4—C51.374 (4)C21—N41.359 (3)
C4—H4A0.9300C21—C201.503 (3)
C5—C61.398 (3)C22—N31.366 (3)
C5—H5A0.9300C22—C231.499 (3)
C6—C71.431 (3)C23—H23A0.9600
C7—N11.294 (3)C23—H23B0.9600
C7—C81.500 (3)C23—H23C0.9600
C8—C91.514 (3)O1—N11.432 (3)
C8—C121.524 (3)O3—N51.222 (3)
C8—H8A0.9800O4—N51.220 (3)
C9—C101.511 (3)O5—N51.204 (3)
C9—H9A0.9700N2—H2B0.89 (3)
C9—H9B0.9700N4—C171.482 (3)
C10—N21.492 (3)C17—C181.600 (7)
C10—H10A0.9700C17—H17A0.9700
C10—H10B0.9700C17—H17B0.9700
C11—N21.489 (3)C20—C191.448 (5)
C11—C121.515 (3)C18—C191.488 (9)
C11—H11A0.9700C18—H18A0.9700
C11—H11B0.9700C18—H18B0.9700
C12—H12A0.9700C19—H19A0.9700
C12—H12B0.9700C19—H19B0.9700
C13—N21.501 (3)C18'—C19'1.528 (14)
C13—C141.511 (3)C18'—H18C0.9700
C13—H13A0.9700C18'—H18D0.9700
C13—H13B0.9700C19'—H19C0.9700
C14—C151.507 (3)C19'—H19D0.9700
O1—C1—C6109.8 (2)C13—C14—H14B109.9
O1—C1—C2125.8 (2)H14A—C14—H14B108.3
C6—C1—C2124.4 (2)C22—C15—C16118.6 (2)
C3—C2—C1113.7 (2)C22—C15—C14124.9 (2)
C3—C2—H2A123.2C16—C15—C14116.4 (2)
C1—C2—H2A123.2O2—C16—N4119.5 (2)
F—C3—C2117.6 (2)O2—C16—C15124.9 (2)
F—C3—C4117.0 (3)N4—C16—C15115.6 (2)
C2—C3—C4125.4 (2)N3—C21—N4123.2 (2)
C5—C4—C3118.9 (3)N3—C21—C20117.1 (2)
C5—C4—H4A120.6N4—C21—C20119.6 (2)
C3—C4—H4A120.6C15—C22—N3123.2 (2)
C4—C5—C6118.6 (2)C15—C22—C23122.5 (2)
C4—C5—H5A120.7N3—C22—C23114.3 (2)
C6—C5—H5A120.7C22—C23—H23A109.5
C1—C6—C5119.1 (2)C22—C23—H23B109.5
C1—C6—C7104.1 (2)H23A—C23—H23B109.5
C5—C6—C7136.8 (2)C22—C23—H23C109.5
N1—C7—C6111.6 (2)H23A—C23—H23C109.5
N1—C7—C8120.6 (2)H23B—C23—H23C109.5
C6—C7—C8127.8 (2)C1—O1—N1107.44 (17)
C7—C8—C9112.95 (19)C7—N1—O1107.01 (19)
C7—C8—C12110.41 (19)C11—N2—C10110.68 (19)
C9—C8—C12108.51 (19)C11—N2—C13111.98 (18)
C7—C8—H8A108.3C10—N2—C13109.88 (18)
C9—C8—H8A108.3C11—N2—H2B108.8 (18)
C12—C8—H8A108.3C10—N2—H2B108.2 (18)
C10—C9—C8111.8 (2)C13—N2—H2B107.1 (18)
C10—C9—H9A109.3C21—N3—C22118.23 (19)
C8—C9—H9A109.3C21—N4—C16121.04 (19)
C10—C9—H9B109.3C21—N4—C17123.4 (2)
C8—C9—H9B109.3C16—N4—C17115.6 (2)
H9A—C9—H9B107.9O5—N5—O4125.4 (3)
N2—C10—C9111.29 (19)O5—N5—O3115.1 (3)
N2—C10—H10A109.4O4—N5—O3119.4 (3)
C9—C10—H10A109.4N4—C17—C18109.0 (3)
N2—C10—H10B109.4N4—C17—H17A109.9
C9—C10—H10B109.4C18—C17—H17A109.9
H10A—C10—H10B108.0N4—C17—H17B109.9
N2—C11—C12112.12 (19)C18—C17—H17B109.9
N2—C11—H11A109.2H17A—C17—H17B108.3
C12—C11—H11A109.2C19—C20—C21119.1 (3)
N2—C11—H11B109.2C19—C18—C17112.1 (5)
C12—C11—H11B109.2C19—C18—H18A109.2
H11A—C11—H11B107.9C17—C18—H18A109.2
C11—C12—C8111.5 (2)C19—C18—H18B109.2
C11—C12—H12A109.3C17—C18—H18B109.2
C8—C12—H12A109.3H18A—C18—H18B107.9
C11—C12—H12B109.3C20—C19—C18107.0 (5)
C8—C12—H12B109.3C20—C19—H19A110.3
H12A—C12—H12B108.0C18—C19—H19A110.3
N2—C13—C14114.32 (19)C20—C19—H19B110.3
N2—C13—H13A108.7C18—C19—H19B110.3
C14—C13—H13A108.7H19A—C19—H19B108.6
N2—C13—H13B108.7C19'—C18'—H18C110.4
C14—C13—H13B108.7C19'—C18'—H18D110.4
H13A—C13—H13B107.6H18C—C18'—H18D108.6
C15—C14—C13108.73 (19)C18'—C19'—H19C109.1
C15—C14—H14A109.9C18'—C19'—H19D109.1
C13—C14—H14A109.9H19C—C19'—H19D107.9
C15—C14—H14B109.9
O1—C1—C2—C3179.6 (2)C16—C15—C22—N32.6 (4)
C6—C1—C2—C30.7 (4)C14—C15—C22—N3179.2 (2)
C1—C2—C3—F177.2 (2)C16—C15—C22—C23177.2 (2)
C1—C2—C3—C41.5 (4)C14—C15—C22—C230.6 (4)
F—C3—C4—C5176.5 (2)C6—C1—O1—N10.4 (2)
C2—C3—C4—C52.2 (4)C2—C1—O1—N1178.6 (2)
C3—C4—C5—C60.6 (4)C6—C7—N1—O11.0 (3)
O1—C1—C6—C5178.8 (2)C8—C7—N1—O1177.04 (19)
C2—C1—C6—C52.2 (4)C1—O1—N1—C70.4 (2)
O1—C1—C6—C70.9 (2)C12—C11—N2—C1055.2 (3)
C2—C1—C6—C7178.1 (2)C12—C11—N2—C13178.1 (2)
C4—C5—C6—C11.4 (4)C9—C10—N2—C1155.7 (3)
C4—C5—C6—C7179.0 (3)C9—C10—N2—C13179.9 (2)
C1—C6—C7—N11.2 (3)C14—C13—N2—C1172.5 (3)
C5—C6—C7—N1178.4 (3)C14—C13—N2—C10164.0 (2)
C1—C6—C7—C8176.6 (2)N4—C21—N3—C221.6 (3)
C5—C6—C7—C83.7 (4)C20—C21—N3—C22177.1 (2)
N1—C7—C8—C915.8 (3)C15—C22—N3—C210.4 (3)
C6—C7—C8—C9166.5 (2)C23—C22—N3—C21179.8 (2)
N1—C7—C8—C12105.9 (3)N3—C21—N4—C160.4 (3)
C6—C7—C8—C1271.8 (3)C20—C21—N4—C16179.0 (2)
C7—C8—C9—C10179.3 (2)N3—C21—N4—C17179.8 (2)
C12—C8—C9—C1056.6 (3)C20—C21—N4—C171.2 (3)
C8—C9—C10—N257.8 (3)O2—C16—N4—C21176.7 (2)
N2—C11—C12—C856.0 (3)C15—C16—N4—C213.3 (3)
C7—C8—C12—C11179.7 (2)O2—C16—N4—C173.1 (3)
C9—C8—C12—C1155.4 (3)C15—C16—N4—C17176.9 (2)
N2—C13—C14—C15169.70 (19)C21—N4—C17—C1818.7 (4)
C13—C14—C15—C2286.2 (3)C16—N4—C17—C18161.5 (3)
C13—C14—C15—C1690.5 (3)N3—C21—C20—C19167.1 (4)
C22—C15—C16—O2175.7 (2)N4—C21—C20—C1914.2 (5)
C14—C15—C16—O21.1 (4)N4—C17—C18—C1950.2 (7)
C22—C15—C16—N44.3 (3)C21—C20—C19—C1843.9 (7)
C14—C15—C16—N4178.9 (2)C17—C18—C19—C2062.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O3i0.89 (3)2.07 (3)2.866 (3)149 (2)
N2—H2B···O5i0.89 (3)2.33 (3)3.157 (5)156 (2)
C2—H2A···O2ii0.932.193.107 (3)171
C10—H10A···O40.972.503.221 (4)131
C13—H13B···Fiii0.972.333.264 (3)161
Symmetry codes: (i) x+1, y, z; (ii) x, y+1/2, z1/2; (iii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC23H28FN4O2+·NO3
Mr473.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.1655 (16), 21.866 (4), 12.635 (3)
β (°) 91.94 (3)
V3)2254.6 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.15 × 0.12 × 0.09
Data collection
DiffractometerRigaku Scxmini 1K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.94, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
22497, 5164, 3386
Rint0.047
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.176, 1.04
No. of reflections5164
No. of parameters325
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.28

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O3i0.89 (3)2.07 (3)2.866 (3)149 (2)
N2—H2B···O5i0.89 (3)2.33 (3)3.157 (5)156 (2)
C2—H2A···O2ii0.932.193.107 (3)171
C10—H10A···O40.972.503.221 (4)131
C13—H13B···Fiii0.972.333.264 (3)161
Symmetry codes: (i) x+1, y, z; (ii) x, y+1/2, z1/2; (iii) x+1, y1/2, z+3/2.
 

References

First citationCallaghan, J. T., Bergstrom, R. F., Ptak, L. R. & Beasley, C. M. (1999). Clin. Pharm. 37, 177–193.  Web of Science CrossRef CAS Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTandon, R. (2002). Psychiatr. Q. 73, 297–311.  Web of Science CrossRef PubMed Google Scholar

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