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In the structure of the title compound, C19H21N5O3S, the piperazine ring adopts a slightly deformed chair conformation, with puckering parameters Q = 0.534 (2) Å and θ = 22.2 (2)° and an almost flat configuration of the piperazine N atom bonded to the benzene ring. This deformation is caused by the strong conjugation effect of the lone pair of the N atom with the π-electron system of the benzene ring in the aryl­piperazine part of the mol­ecule. The mol­ecular packing is influenced by weak π–π inter­actions of the isothia­zolopyridine systems, with a shortest centroid-to-centroid separation of 3.5113 (14) Å between pyridine rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503117X/lh6501sup1.cif
Contains datablocks global, IId

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680503117X/lh6501IIdsup2.hkl
Contains datablock IId

CCDC reference: 290311

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.134
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for O38 - N37 .. 5.60 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

4,6-Dimethyl-2-[4-(4-nitrophenyl)piperazin-1- ylmethyl]isothiazolo[5,4-b]pyridin-3(2H)-one top
Crystal data top
C19H21N5O3SZ = 2
Mr = 399.47F(000) = 420
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: -P 1Melting point = 474–476 K
a = 7.879 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.825 (2) ÅCell parameters from 704 reflections
c = 14.927 (3) Åθ = 3.0–69.5°
α = 99.94 (3)°µ = 1.82 mm1
β = 101.43 (3)°T = 293 K
γ = 109.04 (3)°Prism, yellow
V = 929.6 (5) Å30.35 × 0.25 × 0.15 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
3403 independent reflections
Radiation source: fine-focus sealed tube3190 reflections with I > \2s(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 70.1°, θmin = 3.1°
Absorption correction: multi-scan
[SADABS (Sheldrick, 2002), based on the method of Blessing (1995)]
h = 89
Tmin = 0.633, Tmax = 0.764k = 1010
10692 measured reflectionsl = 1818
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)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0961P)2 + 0.0935P]
where P = (Fo2 + 2Fc2)/3
3403 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. Ratio of minimum to maximum apparent transmission: 0.827920

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.2084 (0.0044) x - 4.4754 (0.0047) y - 6.6599 (0.0097) z = 4.0244 (0.0028)

* 0.0105 (0.0007) S1 * -0.0168 (0.0009) N2 * 0.0156 (0.0010) C3 * -0.0059 (0.0010) C9 * -0.0035 (0.0008) C8 0.0523 (0.0024) O3 0.2645 (0.0028) C12

Rms deviation of fitted atoms = 0.0117

7.0856 (0.0043) x - 4.6338 (0.0053) y - 6.8645 (0.0088) z = 4.0442 (0.0031)

Angle to previous plane (with approximate e.s.d.) = 2.16 (0.08)

* -0.0040 (0.0011) C4 * 0.0041 (0.0011) C5 * -0.0017 (0.0010) C6 * -0.0008 (0.0010) N7 * 0.0008 (0.0010) C8 * 0.0016 (0.0010) C9 - 0.0524 (0.0031) C10 - 0.0221 (0.0027) C11

Rms deviation of fitted atoms = 0.0026

7.1390 (0.0039) x - 4.5653 (0.0040) y - 6.7816 (0.0069) z = 4.0113 (0.0025)

Angle to previous plane (with approximate e.s.d.) = 0.92 (0.07)

* 0.0020 (0.0008) S1 * -0.0378 (0.0012) N2 * 0.0154 (0.0012) C3 * -0.0039 (0.0012) C4 * -0.0125 (0.0013) C5 * -0.0148 (0.0011) C6 * 0.0057 (0.0010) N7 * 0.0235 (0.0013) C8 * 0.0225 (0.0013) C9 - 0.0560 (0.0029) C10 - 0.0537 (0.0023) C11 0.2125 (0.0023) C12 0.0462 (0.0021) O3

Rms deviation of fitted atoms = 0.0187

7.3725 (0.0042) x - 2.7583 (0.0054) y + 2.2491 (0.0096) z = 5.0983 (0.0048)

Angle to previous plane (with approximate e.s.d.) = 43.49 (0.04)

* -0.0102 (0.0010) C31 * 0.0119 (0.0011) C32 * -0.0043 (0.0011) C33 * -0.0051 (0.0011) C34 * 0.0064 (0.0011) C35 * 0.0012 (0.0011) C36 - 0.0147 (0.0022) N37 - 0.1466 (0.0028) O38 0.1138 (0.0027) O39

Rms deviation of fitted atoms = 0.0075

7.6328 (0.0044) x - 3.2989 (0.0094) y + 0.7630 (0.0146) z = 4.8885 (0.0049)

Angle to previous plane (with approximate e.s.d.) = 7.38 (0.08)

* -0.0017 (0.0010) C22 * 0.0016 (0.0009) C23 * -0.0016 (0.0009) C25 * 0.0017 (0.0010) C26 0.7216 (0.0024) N21 - 0.4158 (0.0024) N24

Rms deviation of fitted atoms = 0.0016

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*/Ueq
S10.48172 (6)0.18807 (5)0.04192 (3)0.07101 (19)
O30.4844 (2)0.45259 (17)0.21625 (9)0.0787 (4)
O380.8643 (3)1.01920 (16)0.61839 (10)0.0868 (4)
O390.8201 (2)0.89670 (17)0.72875 (9)0.0829 (4)
N20.5434 (2)0.23756 (18)0.14606 (11)0.0665 (4)
N70.20006 (19)0.42763 (16)0.09385 (9)0.0596 (3)
N210.7137 (2)0.01542 (17)0.27949 (10)0.0633 (3)
N240.67208 (17)0.28923 (15)0.38921 (9)0.0533 (3)
N370.8263 (2)0.89334 (18)0.64734 (10)0.0641 (3)
C30.4493 (2)0.3987 (2)0.14764 (11)0.0599 (4)
C40.1733 (3)0.64672 (19)0.02686 (11)0.0610 (4)
C50.0573 (3)0.6917 (2)0.06372 (12)0.0635 (4)
H510.046 (4)0.800 (3)0.0892 (17)0.095*
C60.0720 (2)0.5820 (2)0.12174 (11)0.0583 (4)
C80.3121 (2)0.38592 (19)0.00664 (11)0.0547 (3)
C90.3087 (2)0.48501 (18)0.05668 (11)0.0551 (4)
C100.1525 (4)0.7619 (2)0.09023 (15)0.0859 (6)
H1010.26420.78490.10580.129*
H1020.04840.86360.05840.129*
H1030.13160.71120.14710.129*
C110.0579 (3)0.6328 (3)0.21856 (12)0.0729 (5)
H1110.11010.55010.22640.109*
H1120.15650.73700.22680.109*
H1130.00930.64390.26480.109*
C120.7185 (3)0.1272 (2)0.21915 (15)0.0695 (4)
H1210.752 (4)0.201 (3)0.2605 (19)0.104*
H1220.803 (4)0.091 (3)0.1893 (19)0.104*
C220.5996 (3)0.0144 (2)0.34395 (14)0.0660 (4)
H2210.461 (4)0.048 (3)0.3080 (18)0.099*
H2220.615 (4)0.102 (3)0.3717 (19)0.099*
C230.6593 (3)0.1410 (2)0.42336 (12)0.0613 (4)
H2310.787 (4)0.163 (3)0.4656 (18)0.092*
H2320.572 (3)0.130 (3)0.4633 (17)0.092*
C250.7405 (3)0.3025 (2)0.30502 (12)0.0627 (4)
H2510.692 (4)0.371 (3)0.2730 (18)0.094*
H2520.878 (4)0.355 (3)0.3283 (18)0.094*
C260.6771 (3)0.1383 (2)0.23377 (13)0.0664 (4)
H2610.540 (4)0.107 (3)0.2027 (18)0.100*
H2620.751 (4)0.149 (3)0.1878 (19)0.100*
C310.71464 (19)0.43599 (18)0.45444 (10)0.0505 (3)
C320.6918 (2)0.4421 (2)0.54647 (11)0.0555 (3)
H3210.648 (3)0.341 (3)0.5640 (16)0.083*
C330.7258 (2)0.5895 (2)0.60875 (11)0.0575 (4)
H3310.695 (3)0.589 (3)0.6697 (17)0.086*
C340.7887 (2)0.73688 (19)0.58290 (10)0.0544 (3)
C350.8172 (2)0.7365 (2)0.49405 (11)0.0580 (4)
H3510.868 (3)0.840 (3)0.4764 (17)0.087*
C360.7809 (2)0.59034 (19)0.43154 (11)0.0580 (4)
H3610.803 (3)0.595 (3)0.3721 (17)0.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0749 (3)0.0545 (3)0.0736 (3)0.0146 (2)0.0094 (2)0.0229 (2)
O30.0979 (10)0.0745 (8)0.0622 (7)0.0345 (7)0.0094 (6)0.0233 (6)
O380.1266 (13)0.0600 (7)0.0732 (8)0.0360 (8)0.0223 (8)0.0188 (6)
O390.1010 (10)0.0782 (8)0.0566 (7)0.0232 (7)0.0184 (6)0.0085 (6)
N20.0693 (8)0.0560 (7)0.0657 (8)0.0212 (6)0.0055 (6)0.0135 (6)
N70.0667 (8)0.0607 (7)0.0542 (7)0.0252 (6)0.0183 (6)0.0167 (6)
N210.0628 (8)0.0572 (7)0.0685 (8)0.0249 (6)0.0129 (6)0.0133 (6)
N240.0539 (7)0.0508 (6)0.0551 (7)0.0177 (5)0.0134 (5)0.0185 (5)
N370.0641 (8)0.0650 (8)0.0560 (7)0.0218 (6)0.0076 (6)0.0116 (6)
C30.0703 (9)0.0555 (8)0.0578 (8)0.0290 (7)0.0167 (7)0.0142 (6)
C40.0791 (10)0.0499 (8)0.0574 (8)0.0246 (7)0.0251 (7)0.0139 (6)
C50.0748 (10)0.0524 (8)0.0593 (8)0.0195 (7)0.0228 (7)0.0075 (7)
C60.0646 (9)0.0592 (8)0.0535 (8)0.0255 (7)0.0219 (7)0.0093 (6)
C80.0602 (8)0.0526 (8)0.0567 (8)0.0241 (6)0.0203 (6)0.0168 (6)
C90.0669 (9)0.0513 (7)0.0532 (7)0.0268 (7)0.0211 (7)0.0139 (6)
C100.1216 (18)0.0573 (10)0.0733 (11)0.0211 (10)0.0283 (11)0.0250 (8)
C110.0767 (11)0.0777 (11)0.0568 (9)0.0262 (9)0.0144 (8)0.0084 (8)
C120.0610 (9)0.0618 (10)0.0774 (11)0.0260 (8)0.0062 (8)0.0055 (8)
C220.0689 (10)0.0527 (8)0.0747 (10)0.0200 (7)0.0165 (8)0.0209 (8)
C230.0660 (9)0.0551 (8)0.0640 (9)0.0211 (7)0.0158 (7)0.0237 (7)
C250.0742 (10)0.0567 (9)0.0587 (9)0.0225 (8)0.0216 (8)0.0183 (7)
C260.0776 (11)0.0574 (9)0.0632 (9)0.0241 (8)0.0185 (8)0.0157 (7)
C310.0426 (6)0.0546 (8)0.0525 (7)0.0166 (6)0.0083 (5)0.0178 (6)
C320.0531 (8)0.0566 (8)0.0541 (8)0.0153 (6)0.0106 (6)0.0222 (6)
C330.0529 (8)0.0667 (9)0.0488 (7)0.0186 (7)0.0083 (6)0.0185 (6)
C340.0480 (7)0.0572 (8)0.0528 (8)0.0183 (6)0.0056 (6)0.0134 (6)
C350.0584 (8)0.0551 (8)0.0586 (8)0.0175 (6)0.0136 (6)0.0201 (7)
C360.0636 (9)0.0567 (8)0.0551 (8)0.0195 (7)0.0187 (7)0.0210 (7)
Geometric parameters (Å, º) top
S1—N21.7078 (16)C10—H1030.9600
S1—C81.7369 (18)C11—H1110.9600
O3—C31.222 (2)C11—H1120.9600
O38—N371.229 (2)C11—H1130.9600
O39—N371.2213 (19)C12—H1211.03 (3)
N2—C31.380 (2)C12—H1220.88 (3)
N2—C121.484 (2)C22—C231.518 (3)
N7—C81.333 (2)C22—H2211.04 (3)
N7—C61.337 (2)C22—H2220.97 (3)
N21—C121.432 (2)C23—H2311.02 (3)
N21—C221.442 (2)C23—H2320.99 (2)
N21—C261.451 (2)C25—C261.505 (2)
N24—C311.375 (2)C25—H2510.96 (3)
N24—C231.465 (2)C25—H2520.99 (3)
N24—C251.470 (2)C26—H2611.01 (3)
N37—C341.443 (2)C26—H2620.98 (3)
C3—C91.465 (2)C31—C321.415 (2)
C4—C51.382 (3)C31—C361.419 (2)
C4—C91.404 (2)C32—C331.373 (2)
C4—C101.497 (2)C32—H3210.95 (2)
C5—C61.399 (2)C33—C341.384 (2)
C5—H510.98 (3)C33—H3310.99 (2)
C6—C111.492 (3)C34—C351.388 (2)
C8—C91.392 (2)C35—C361.361 (2)
C10—H1010.9600C35—H3510.97 (3)
C10—H1020.9600C36—H3610.94 (2)
N2—S1—C890.62 (8)N2—C12—H121105.4 (15)
C3—N2—C12122.11 (16)N21—C12—H122107.0 (18)
C3—N2—S1115.84 (12)N2—C12—H122107.1 (18)
C12—N2—S1120.20 (13)H121—C12—H122112 (2)
C8—N7—C6115.06 (14)N21—C22—C23109.95 (14)
C12—N21—C22116.90 (15)N21—C22—H221109.7 (14)
C12—N21—C26116.25 (15)C23—C22—H221109.8 (14)
C22—N21—C26108.59 (14)N21—C22—H222110.0 (15)
C31—N24—C23118.29 (12)C23—C22—H222108.0 (16)
C31—N24—C25116.17 (12)H221—C22—H222109 (2)
C23—N24—C25117.30 (13)N24—C23—C22112.99 (14)
O39—N37—O38122.17 (15)N24—C23—H231107.1 (14)
O39—N37—C34119.13 (15)C22—C23—H231109.7 (14)
O38—N37—C34118.70 (13)N24—C23—H232107.2 (14)
O3—C3—N2122.74 (16)C22—C23—H232111.8 (14)
O3—C3—C9128.52 (16)H231—C23—H232107.7 (19)
N2—C3—C9108.74 (14)N24—C25—C26113.10 (14)
C5—C4—C9115.98 (15)N24—C25—H251109.6 (15)
C5—C4—C10121.97 (17)C26—C25—H251105.9 (15)
C9—C4—C10122.03 (17)N24—C25—H252106.2 (14)
C4—C5—C6122.03 (16)C26—C25—H252112.0 (14)
C4—C5—H51121.6 (14)H251—C25—H252110 (2)
C6—C5—H51116.2 (15)N21—C26—C25110.38 (15)
N7—C6—C5122.41 (16)N21—C26—H261112.7 (15)
N7—C6—C11116.70 (16)C25—C26—H261106.7 (15)
C5—C6—C11120.88 (16)N21—C26—H262105.5 (16)
N7—C8—C9127.05 (15)C25—C26—H262109.6 (15)
N7—C8—S1121.01 (12)H261—C26—H262112 (2)
C9—C8—S1111.91 (13)N24—C31—C32122.47 (13)
C8—C9—C4117.46 (15)N24—C31—C36121.06 (13)
C8—C9—C3112.81 (14)C32—C31—C36116.45 (14)
C4—C9—C3129.71 (15)C33—C32—C31121.46 (14)
C4—C10—H101109.5C33—C32—H321120.0 (14)
C4—C10—H102109.5C31—C32—H321118.5 (14)
H101—C10—H102109.5C32—C33—C34119.98 (14)
C4—C10—H103109.5C32—C33—H331119.6 (13)
H101—C10—H103109.5C34—C33—H331120.2 (13)
H102—C10—H103109.5C35—C34—C33120.29 (15)
C6—C11—H111109.5C35—C34—N37118.76 (14)
C6—C11—H112109.5C33—C34—N37120.96 (14)
H111—C11—H112109.5C36—C35—C34119.92 (15)
C6—C11—H113109.5C36—C35—H351119.0 (14)
H111—C11—H113109.5C34—C35—H351121.0 (14)
H112—C11—H113109.5C35—C36—C31121.87 (15)
N21—C12—N2117.34 (15)C35—C36—H361117.5 (14)
N21—C12—H121108.3 (15)C31—C36—H361120.6 (14)
C8—S1—N2—C32.41 (13)C3—N2—C12—N21114.8 (2)
C8—S1—N2—C12167.25 (14)S1—N2—C12—N2181.3 (2)
C12—N2—C3—O312.6 (3)C12—N21—C22—C23160.63 (15)
S1—N2—C3—O3177.15 (14)C26—N21—C22—C2365.43 (19)
C12—N2—C3—C9167.54 (15)C31—N24—C23—C22176.38 (13)
S1—N2—C3—C93.01 (18)C25—N24—C23—C2236.3 (2)
C9—C4—C5—C60.9 (2)N21—C22—C23—N2450.4 (2)
C10—C4—C5—C6177.53 (17)C31—N24—C25—C26175.91 (14)
C8—N7—C6—C50.2 (2)C23—N24—C25—C2636.1 (2)
C8—N7—C6—C11179.20 (14)C12—N21—C26—C25160.35 (16)
C4—C5—C6—N70.7 (2)C22—N21—C26—C2565.38 (19)
C4—C5—C6—C11178.68 (16)N24—C25—C26—N2149.7 (2)
C6—N7—C8—C90.0 (2)C23—N24—C31—C3219.4 (2)
C6—N7—C8—S1178.10 (10)C25—N24—C31—C32167.05 (14)
N2—S1—C8—N7177.35 (13)C23—N24—C31—C36161.86 (15)
N2—S1—C8—C91.00 (12)C25—N24—C31—C3614.2 (2)
N7—C8—C9—C40.2 (2)N24—C31—C32—C33176.48 (13)
S1—C8—C9—C4178.03 (11)C36—C31—C32—C332.3 (2)
N7—C8—C9—C3178.73 (14)C31—C32—C33—C341.8 (2)
S1—C8—C9—C30.49 (17)C32—C33—C34—C350.2 (2)
C5—C4—C9—C80.6 (2)C32—C33—C34—N37179.66 (13)
C10—C4—C9—C8177.80 (16)O39—N37—C34—C35172.54 (16)
C5—C4—C9—C3178.87 (15)O38—N37—C34—C357.2 (2)
C10—C4—C9—C30.4 (3)O39—N37—C34—C337.3 (2)
O3—C3—C9—C8178.01 (17)O38—N37—C34—C33172.99 (16)
N2—C3—C9—C82.17 (19)C33—C34—C35—C360.8 (2)
O3—C3—C9—C43.7 (3)N37—C34—C35—C36179.30 (14)
N2—C3—C9—C4176.13 (15)C34—C35—C36—C310.3 (2)
C22—N21—C12—N266.8 (2)N24—C31—C36—C35177.54 (14)
C26—N21—C12—N263.6 (2)C32—C31—C36—C351.3 (2)
 

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