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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1647.
Published online 2009 June 20. doi:  10.1107/S1600536809022016
PMCID: PMC2969342

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

Abstract

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 [triangle]); Tandon (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1647-scheme1.jpg

Experimental

Crystal data

  • C23H28FN4O2 +·NO3
  • M r = 473.50
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1647-efi5.jpg
  • 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) T min = 0.94, T max = 0.99
  • 22497 measured reflections
  • 5164 independent reflections
  • 3386 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022016/xu2503sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022016/xu2503Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
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).

Crystal data

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

Rigaku Scxmini 1K CCD area-detector diffractometer5164 independent reflections
Radiation source: fine-focus sealed tube3386 reflections with I > 2σ(I)
graphiteRint = 0.047
Detector resolution: 8.192 pixels mm-1θmax = 27.5°, θmin = 3.1°
Thin–slice ω scansh = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −28→28
Tmin = 0.94, Tmax = 0.99l = −16→16
22497 measured reflections

Refinement

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 = 1.04w = 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

Special details

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)

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)
H13A0.8132−0.02270.65050.048*
H13B0.7186−0.00050.74910.048*
C140.9607 (3)−0.01635 (11)0.7837 (2)0.0427 (6)
H14A1.0595−0.02000.74360.051*
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)
H23A1.0477−0.09870.65330.076*
H23B0.9465−0.15860.63100.076*
H23C1.1200−0.16240.68760.076*
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)
H17A0.6095−0.12111.06970.069*
H17B0.7771−0.09981.12250.069*
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)
H18A0.8605−0.20241.15510.068*0.620 (11)
H18B0.6824−0.19751.19720.068*0.620 (11)
C190.6928 (8)−0.2473 (2)1.0624 (4)0.0495 (15)0.620 (11)
H19A0.7033−0.28621.09880.059*0.620 (11)
H19B0.5792−0.24181.03940.059*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)
H20B0.8883−0.27390.96320.066*
H20C0.7004−0.26350.93830.066*
C18'0.6516 (13)−0.1831 (4)1.1149 (6)0.053 (3)0.380 (11)
H18C0.5475−0.18991.07740.063*0.380 (11)
H18D0.6321−0.17961.18990.063*0.380 (11)
C19'0.7689 (15)−0.2360 (4)1.0947 (8)0.053 (2)*0.380 (11)
H19C0.7247−0.27321.12410.064*0.380 (11)
H19D0.8733−0.22781.13090.064*0.380 (11)
H2B0.933 (4)0.0742 (12)0.652 (2)0.052 (8)*

Atomic displacement parameters (Å2)

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, °)

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—C3−179.6 (2)C16—C15—C22—N3−2.6 (4)
C6—C1—C2—C3−0.7 (4)C14—C15—C22—N3−179.2 (2)
C1—C2—C3—F177.2 (2)C16—C15—C22—C23177.2 (2)
C1—C2—C3—C4−1.5 (4)C14—C15—C22—C230.6 (4)
F—C3—C4—C5−176.5 (2)C6—C1—O1—N1−0.4 (2)
C2—C3—C4—C52.2 (4)C2—C1—O1—N1178.6 (2)
C3—C4—C5—C6−0.6 (4)C6—C7—N1—O11.0 (3)
O1—C1—C6—C5−178.8 (2)C8—C7—N1—O1−177.04 (19)
C2—C1—C6—C52.2 (4)C1—O1—N1—C7−0.4 (2)
O1—C1—C6—C70.9 (2)C12—C11—N2—C10−55.2 (3)
C2—C1—C6—C7−178.1 (2)C12—C11—N2—C13−178.1 (2)
C4—C5—C6—C1−1.4 (4)C9—C10—N2—C1155.7 (3)
C4—C5—C6—C7179.0 (3)C9—C10—N2—C13179.9 (2)
C1—C6—C7—N1−1.2 (3)C14—C13—N2—C11−72.5 (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—C8−3.7 (4)C20—C21—N3—C22−177.1 (2)
N1—C7—C8—C9−15.8 (3)C15—C22—N3—C21−0.4 (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—C12−71.8 (3)C20—C21—N4—C16179.0 (2)
C7—C8—C9—C10179.3 (2)N3—C21—N4—C17−179.8 (2)
C12—C8—C9—C1056.6 (3)C20—C21—N4—C17−1.2 (3)
C8—C9—C10—N2−57.8 (3)O2—C16—N4—C21176.7 (2)
N2—C11—C12—C856.0 (3)C15—C16—N4—C21−3.3 (3)
C7—C8—C12—C11−179.7 (2)O2—C16—N4—C17−3.1 (3)
C9—C8—C12—C11−55.4 (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—C18−161.5 (3)
C13—C14—C15—C16−90.5 (3)N3—C21—C20—C19−167.1 (4)
C22—C15—C16—O2−175.7 (2)N4—C21—C20—C1914.2 (5)
C14—C15—C16—O21.1 (4)N4—C17—C18—C19−50.2 (7)
C22—C15—C16—N44.3 (3)C21—C20—C19—C18−43.9 (7)
C14—C15—C16—N4−178.9 (2)C17—C18—C19—C2062.0 (7)

Hydrogen-bond geometry (Å, °)

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, z−1/2; (iii) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2503).

References

  • Callaghan, J. T., Bergstrom, R. F., Ptak, L. R. & Beasley, C. M. (1999). Clin. Pharm 37, 177–193. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tandon, R. (2002). Psychiatr. Q.73, 297–311. [PubMed]

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