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In the crystal structure of the title compound {systematic name: 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-hydr­oxy-1-[2-(2-meth­yl-4-oxo-3,4,6,7,8,9-hexa­hydro-2H-pyrido[1,2-a]pyrimid­in-3-yl)eth­yl]piperidine N-oxide hydrogen peroxide methanol solvate}, C23H27FN4O3·H2O2·CH3OH, the asymmetric unit contains one mol­ecule of risperidone N-oxide, one methanol solvent mol­ecule and one hydrogen peroxide mol­ecule. The piperidine ring adopts a chair conformation, while the tetra­hydro­pyridine ring has a sofa conformation. The hydrogen peroxide mol­ecule links the risperidone mol­ecules to form a chain. O—H...O and C—H...O inter­actions stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022002/bt6696sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022002/bt6696Isup2.hkl
Contains datablock I

CCDC reference: 282244

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.156
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-hydroxy-1-[2-(2-methyl-4-oxo-3,4,6,7,8,9- hexahydro-2H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidine N-oxide top
Crystal data top
C23H27FN4O3·H2O2·CH4OF(000) = 2096
Mr = 492.54Dx = 1.374 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5217 reflections
a = 37.007 (4) Åθ = 2.3–27.6°
b = 7.7558 (8) ŵ = 0.10 mm1
c = 17.214 (2) ÅT = 273 K
β = 105.503 (2)°Block, colorless
V = 4761.0 (9) Å30.20 × 0.15 × 0.10 mm
Z = 8
Data collection top
CCD Area Detector
diffractometer
3527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 1.1°
ω scansh = 4343
11481 measured reflectionsk = 98
4173 independent reflectionsl = 2020
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0833P)2 + 3.9805P]
where P = (Fo2 + 2Fc2)/3
4173 reflections(Δ/σ)max < 0.001
319 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.30 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.05732 (5)0.2528 (3)0.61966 (11)0.0854 (5)
N90.11080 (5)0.0385 (3)0.34716 (12)0.0550 (5)
N140.24427 (4)0.0466 (2)0.36609 (10)0.0334 (4)
N210.39705 (5)0.0779 (2)0.55131 (10)0.0391 (4)
N230.41260 (5)0.1516 (3)0.43295 (11)0.0444 (5)
O80.07856 (4)0.1103 (3)0.36670 (10)0.0602 (5)
O260.33793 (4)0.0069 (2)0.54912 (10)0.0558 (5)
O310.23610 (4)0.08224 (17)0.30736 (8)0.0373 (3)
C20.07801 (7)0.1871 (4)0.57235 (17)0.0580 (7)
C30.11343 (8)0.1259 (4)0.61081 (16)0.0619 (7)
H30.12180.12820.66680.074*
C40.13623 (7)0.0618 (3)0.56632 (15)0.0520 (6)
H40.16010.02000.59110.062*
C50.12228 (6)0.0618 (3)0.48269 (13)0.0419 (5)
C60.08660 (6)0.1225 (3)0.44779 (14)0.0473 (5)
C70.06290 (7)0.1887 (3)0.49147 (17)0.0570 (7)
H70.03890.23000.46730.068*
C100.13571 (6)0.0117 (3)0.41488 (13)0.0408 (5)
C110.17402 (6)0.0558 (3)0.41650 (13)0.0392 (5)
H110.18000.14900.45630.047*
C120.17683 (6)0.1280 (3)0.33627 (13)0.0421 (5)
H12A0.16990.03940.29520.050*
H12B0.15940.22320.32060.050*
C130.21620 (6)0.1899 (3)0.34152 (13)0.0393 (5)
H13A0.21720.23480.28950.047*
H13B0.22260.28290.38050.047*
C150.24204 (6)0.0238 (3)0.44605 (12)0.0387 (5)
H15A0.24940.06550.48670.046*
H15B0.25960.11850.46140.046*
C160.20317 (6)0.0867 (3)0.44422 (13)0.0397 (5)
H16A0.20290.12520.49770.048*
H16B0.19680.18430.40790.048*
C170.28291 (6)0.1173 (3)0.37267 (14)0.0411 (5)
H17A0.29010.19160.41960.049*
H17B0.28210.18730.32550.049*
C180.31266 (6)0.0217 (3)0.37966 (14)0.0431 (5)
H18A0.30620.12050.40790.052*
H18B0.31300.05910.32610.052*
C190.35113 (6)0.0426 (3)0.42420 (13)0.0387 (5)
C200.35987 (6)0.0343 (3)0.51026 (13)0.0393 (5)
C220.42157 (6)0.1366 (3)0.51068 (13)0.0390 (5)
C240.37724 (6)0.1046 (3)0.38878 (13)0.0430 (5)
C250.37055 (8)0.1255 (5)0.29964 (15)0.0727 (9)
H25A0.37920.02450.27770.109*
H25B0.38400.22460.28880.109*
H25C0.34420.14080.27520.109*
C270.40726 (7)0.0559 (3)0.63976 (13)0.0503 (6)
H27A0.39650.05080.65260.060*
H27B0.39650.14980.66340.060*
C280.44907 (7)0.0521 (4)0.67688 (15)0.0629 (7)
H28A0.45430.05970.73510.076*
H28B0.45920.05620.66380.076*
C290.46758 (7)0.1980 (4)0.64647 (15)0.0639 (7)
H29A0.49430.19650.67230.077*
H29B0.45750.30650.65940.077*
C300.46092 (6)0.1823 (4)0.55679 (14)0.0529 (6)
H30A0.47770.09510.54600.064*
H30B0.46750.29100.53630.064*
O320.47741 (6)0.1987 (3)0.37247 (14)0.0868 (7)
H320.45880.17690.38800.130*
C330.47294 (10)0.3566 (6)0.3344 (3)0.1040 (13)
H33A0.47320.44590.37320.156*
H33B0.44940.35890.29380.156*
H33C0.49300.37510.30990.156*
O340.27444 (5)0.4626 (2)0.34180 (10)0.0590 (5)
H340.27330.49600.29600.089*
O350.23793 (6)0.4112 (2)0.34625 (13)0.0659 (5)
H350.23480.30860.33500.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0750 (11)0.1013 (14)0.0928 (12)0.0132 (10)0.0451 (9)0.0086 (11)
N90.0414 (11)0.0676 (14)0.0539 (12)0.0052 (10)0.0089 (9)0.0025 (10)
N140.0352 (9)0.0251 (9)0.0381 (9)0.0006 (7)0.0068 (7)0.0007 (7)
N210.0364 (9)0.0414 (10)0.0419 (9)0.0034 (8)0.0149 (7)0.0050 (8)
N230.0370 (9)0.0546 (12)0.0452 (10)0.0040 (8)0.0170 (8)0.0054 (8)
O80.0390 (9)0.0776 (13)0.0588 (10)0.0115 (8)0.0044 (7)0.0044 (9)
O260.0453 (9)0.0689 (12)0.0602 (10)0.0067 (8)0.0261 (8)0.0089 (9)
O310.0447 (8)0.0256 (7)0.0403 (8)0.0036 (6)0.0093 (6)0.0035 (6)
C20.0526 (14)0.0574 (16)0.0714 (17)0.0002 (12)0.0297 (13)0.0032 (13)
C30.0597 (16)0.0739 (19)0.0535 (14)0.0001 (14)0.0173 (12)0.0017 (13)
C40.0409 (12)0.0563 (15)0.0561 (14)0.0013 (11)0.0084 (10)0.0052 (11)
C50.0357 (11)0.0361 (12)0.0537 (13)0.0045 (9)0.0116 (9)0.0040 (9)
C60.0379 (11)0.0444 (13)0.0574 (14)0.0030 (10)0.0092 (10)0.0037 (10)
C70.0393 (12)0.0553 (16)0.0783 (18)0.0030 (11)0.0188 (12)0.0035 (13)
C100.0357 (11)0.0354 (12)0.0499 (12)0.0048 (9)0.0090 (9)0.0038 (9)
C110.0356 (11)0.0358 (12)0.0449 (11)0.0029 (9)0.0086 (9)0.0055 (9)
C120.0364 (11)0.0360 (12)0.0494 (12)0.0074 (9)0.0039 (9)0.0041 (9)
C130.0433 (11)0.0261 (10)0.0460 (11)0.0028 (9)0.0076 (9)0.0025 (8)
C150.0374 (11)0.0401 (12)0.0367 (10)0.0056 (9)0.0066 (8)0.0039 (9)
C160.0405 (11)0.0388 (12)0.0405 (11)0.0060 (9)0.0119 (9)0.0066 (9)
C170.0387 (11)0.0317 (11)0.0510 (12)0.0055 (9)0.0087 (9)0.0018 (9)
C180.0380 (11)0.0372 (12)0.0558 (13)0.0032 (9)0.0154 (10)0.0064 (10)
C190.0362 (11)0.0338 (11)0.0472 (12)0.0010 (9)0.0129 (9)0.0013 (9)
C200.0345 (11)0.0345 (12)0.0528 (12)0.0029 (9)0.0181 (9)0.0029 (9)
C220.0354 (11)0.0389 (12)0.0451 (12)0.0024 (9)0.0149 (9)0.0034 (9)
C240.0386 (11)0.0478 (13)0.0441 (12)0.0016 (10)0.0134 (9)0.0009 (10)
C250.0614 (17)0.111 (3)0.0465 (14)0.0189 (17)0.0161 (12)0.0001 (15)
C270.0514 (14)0.0611 (16)0.0412 (12)0.0037 (11)0.0170 (10)0.0059 (11)
C280.0586 (15)0.080 (2)0.0460 (13)0.0029 (14)0.0072 (11)0.0083 (13)
C290.0487 (14)0.082 (2)0.0555 (15)0.0054 (13)0.0048 (12)0.0005 (14)
C300.0361 (12)0.0654 (16)0.0566 (14)0.0041 (11)0.0113 (10)0.0074 (12)
O320.0565 (12)0.117 (2)0.0951 (15)0.0005 (12)0.0348 (11)0.0176 (14)
C330.072 (2)0.126 (3)0.115 (3)0.004 (2)0.027 (2)0.039 (3)
O340.0698 (12)0.0486 (11)0.0509 (10)0.0068 (8)0.0027 (8)0.0034 (8)
O350.0905 (14)0.0361 (9)0.0842 (13)0.0008 (9)0.0460 (11)0.0022 (9)
Geometric parameters (Å, º) top
F1—C21.357 (3)C15—H15B0.9700
N9—C101.295 (3)C16—H16A0.9700
N9—O81.436 (3)C16—H16B0.9700
N14—O311.396 (2)C17—C181.522 (3)
N14—C131.503 (3)C17—H17A0.9700
N14—C151.503 (3)C17—H17B0.9700
N14—C171.507 (3)C18—C191.510 (3)
N21—C221.364 (3)C18—H18A0.9700
N21—C201.410 (3)C18—H18B0.9700
N21—C271.477 (3)C19—C241.361 (3)
N23—C221.295 (3)C19—C201.431 (3)
N23—C241.375 (3)C22—C301.503 (3)
O8—C61.351 (3)C24—C251.496 (3)
O26—C201.224 (2)C25—H25A0.9600
C2—C71.355 (4)C25—H25B0.9600
C2—C31.385 (4)C25—H25C0.9600
C3—C41.375 (3)C27—C281.508 (3)
C3—H30.9300C27—H27A0.9700
C4—C51.393 (3)C27—H27B0.9700
C4—H40.9300C28—C291.489 (4)
C5—C61.379 (3)C28—H28A0.9700
C5—C101.439 (3)C28—H28B0.9700
C6—C71.396 (3)C29—C301.502 (3)
C7—H70.9300C29—H29A0.9700
C10—C111.505 (3)C29—H29B0.9700
C11—C121.519 (3)C30—H30A0.9700
C11—C161.529 (3)C30—H30B0.9700
C11—H110.9800O32—C331.378 (4)
C12—C131.514 (3)O32—H320.8200
C12—H12A0.9700C33—H33A0.9600
C12—H12B0.9700C33—H33B0.9600
C13—H13A0.9700C33—H33C0.9600
C13—H13B0.9700O34—O351.430 (3)
C15—C161.511 (3)O34—H340.8200
C15—H15A0.9700O35—H350.8200
C10—N9—O8106.70 (18)N14—C17—C18113.56 (17)
O31—N14—C13109.02 (14)N14—C17—H17A108.9
O31—N14—C15110.43 (14)C18—C17—H17A108.9
C13—N14—C15108.86 (15)N14—C17—H17B108.9
O31—N14—C17109.41 (14)C18—C17—H17B108.9
C13—N14—C17108.81 (15)H17A—C17—H17B107.7
C15—N14—C17110.27 (15)C19—C18—C17111.71 (18)
C22—N21—C20121.14 (17)C19—C18—H18A109.3
C22—N21—C27123.05 (18)C17—C18—H18A109.3
C20—N21—C27115.81 (17)C19—C18—H18B109.3
C22—N23—C24119.40 (18)C17—C18—H18B109.3
C6—O8—N9107.58 (16)H18A—C18—H18B107.9
C7—C2—F1118.0 (2)C24—C19—C20119.25 (19)
C7—C2—C3124.9 (2)C24—C19—C18125.1 (2)
F1—C2—C3117.1 (2)C20—C19—C18115.63 (18)
C4—C3—C2120.1 (2)O26—C20—N21119.3 (2)
C4—C3—H3120.0O26—C20—C19125.3 (2)
C2—C3—H3120.0N21—C20—C19115.37 (17)
C3—C4—C5117.5 (2)N23—C22—N21122.55 (19)
C3—C4—H4121.2N23—C22—C30117.98 (18)
C5—C4—H4121.2N21—C22—C30119.45 (19)
C6—C5—C4119.8 (2)C19—C24—N23122.0 (2)
C6—C5—C10103.70 (19)C19—C24—C25123.7 (2)
C4—C5—C10136.5 (2)N23—C24—C25114.25 (19)
O8—C6—C5110.3 (2)C24—C25—H25A109.5
O8—C6—C7125.9 (2)C24—C25—H25B109.5
C5—C6—C7123.8 (2)H25A—C25—H25B109.5
C2—C7—C6113.8 (2)C24—C25—H25C109.5
C2—C7—H7123.1H25A—C25—H25C109.5
C6—C7—H7123.1H25B—C25—H25C109.5
N9—C10—C5111.7 (2)N21—C27—C28112.93 (18)
N9—C10—C11120.9 (2)N21—C27—H27A109.0
C5—C10—C11127.37 (19)C28—C27—H27A109.0
C10—C11—C12113.86 (17)N21—C27—H27B109.0
C10—C11—C16109.68 (18)C28—C27—H27B109.0
C12—C11—C16109.63 (17)H27A—C27—H27B107.8
C10—C11—H11107.8C29—C28—C27110.6 (2)
C12—C11—H11107.8C29—C28—H28A109.5
C16—C11—H11107.8C27—C28—H28A109.5
C13—C12—C11111.19 (17)C29—C28—H28B109.5
C13—C12—H12A109.4C27—C28—H28B109.5
C11—C12—H12A109.4H28A—C28—H28B108.1
C13—C12—H12B109.4C28—C29—C30109.6 (2)
C11—C12—H12B109.4C28—C29—H29A109.8
H12A—C12—H12B108.0C30—C29—H29A109.8
N14—C13—C12111.33 (16)C28—C29—H29B109.8
N14—C13—H13A109.4C30—C29—H29B109.8
C12—C13—H13A109.4H29A—C29—H29B108.2
N14—C13—H13B109.4C29—C30—C22115.57 (19)
C12—C13—H13B109.4C29—C30—H30A108.4
H13A—C13—H13B108.0C22—C30—H30A108.4
N14—C15—C16112.52 (16)C29—C30—H30B108.4
N14—C15—H15A109.1C22—C30—H30B108.4
C16—C15—H15A109.1H30A—C30—H30B107.4
N14—C15—H15B109.1C33—O32—H32109.5
C16—C15—H15B109.1O32—C33—H33A109.5
H15A—C15—H15B107.8O32—C33—H33B109.5
C15—C16—C11111.18 (18)H33A—C33—H33B109.5
C15—C16—H16A109.4O32—C33—H33C109.5
C11—C16—H16A109.4H33A—C33—H33C109.5
C15—C16—H16B109.4H33B—C33—H33C109.5
C11—C16—H16B109.4O35—O34—H34109.5
H16A—C16—H16B108.0O34—O35—H35109.5
C10—N9—O8—C60.1 (3)C10—C11—C16—C15179.61 (17)
C7—C2—C3—C40.5 (5)C12—C11—C16—C1553.9 (2)
F1—C2—C3—C4178.3 (2)O31—N14—C17—C1848.7 (2)
C2—C3—C4—C50.1 (4)C13—N14—C17—C18167.74 (17)
C3—C4—C5—C60.9 (3)C15—N14—C17—C1872.9 (2)
C3—C4—C5—C10179.0 (3)N14—C17—C18—C19152.77 (18)
N9—O8—C6—C50.3 (3)C17—C18—C19—C2496.5 (3)
N9—O8—C6—C7178.9 (2)C17—C18—C19—C2084.0 (2)
C4—C5—C6—O8179.7 (2)C22—N21—C20—O26175.1 (2)
C10—C5—C6—O80.4 (2)C27—N21—C20—O264.8 (3)
C4—C5—C6—C71.1 (4)C22—N21—C20—C195.0 (3)
C10—C5—C6—C7178.8 (2)C27—N21—C20—C19175.12 (18)
F1—C2—C7—C6178.5 (2)C24—C19—C20—O26174.4 (2)
C3—C2—C7—C60.4 (4)C18—C19—C20—O266.1 (3)
O8—C6—C7—C2179.6 (2)C24—C19—C20—N215.7 (3)
C5—C6—C7—C20.5 (4)C18—C19—C20—N21173.83 (18)
O8—N9—C10—C50.2 (3)C24—N23—C22—N210.9 (3)
O8—N9—C10—C11177.09 (18)C24—N23—C22—C30177.6 (2)
C6—C5—C10—N90.4 (3)C20—N21—C22—N231.8 (3)
C4—C5—C10—N9179.7 (3)C27—N21—C22—N23178.3 (2)
C6—C5—C10—C11176.7 (2)C20—N21—C22—C30179.8 (2)
C4—C5—C10—C113.2 (4)C27—N21—C22—C300.1 (3)
N9—C10—C11—C1214.1 (3)C20—C19—C24—N233.4 (3)
C5—C10—C11—C12169.1 (2)C18—C19—C24—N23176.0 (2)
N9—C10—C11—C16109.2 (2)C20—C19—C24—C25177.5 (2)
C5—C10—C11—C1667.6 (3)C18—C19—C24—C253.1 (4)
C10—C11—C12—C13178.73 (17)C22—N23—C24—C190.0 (3)
C16—C11—C12—C1355.4 (2)C22—N23—C24—C25179.1 (2)
O31—N14—C13—C1262.4 (2)C22—N21—C27—C2817.4 (3)
C15—N14—C13—C1258.1 (2)C20—N21—C27—C28162.7 (2)
C17—N14—C13—C12178.32 (17)N21—C27—C28—C2948.4 (3)
C11—C12—C13—N1458.8 (2)C27—C28—C29—C3061.5 (3)
O31—N14—C15—C1662.4 (2)C28—C29—C30—C2244.1 (3)
C13—N14—C15—C1657.2 (2)N23—C22—C30—C29167.9 (2)
C17—N14—C15—C16176.52 (17)N21—C22—C30—C2913.6 (3)
N14—C15—C16—C1156.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O32—H32···N230.822.072.882 (3)173
O34—H34···O31i0.821.842.659 (2)172
O35—H35···O310.821.822.634 (2)170
C4—H4···O34ii0.932.393.267 (3)156
C7—H7···O32iii0.932.483.392 (3)166
C13—H13B···O35iv0.972.543.192 (3)124
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y1/2, z+1; (iii) x1/2, y1/2, z; (iv) x, y+1, z.
 

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