Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C22H24ClN3O3S3, an N-alkoxy-substituted 4-(p-chloro­phenyl)­thia­zole-2(3H)-thione, exhibits a (P) con­figuration at the N-O bond. The p-chloro­phenyl-substit­uent is twisted by -40.3 (6)° out of the thia­zole-2(3H)-thione plane. The piperazino spacer in the N-alkoxy side chain adopts a chair conformation, with its substituents at the N atoms located in equatorial positions. The 1,2-ethanamine bridge, which connects the thia­zole­thione and the piperazine moieties, exhibits an orthogonal arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024814/fl6063sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024814/fl6063Isup2.hkl
Contains datablock I

CCDC reference: 227865

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.062
  • wR factor = 0.135
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.08 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S3 - N2 = 5.18 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C9 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C24 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. S1 = 3.51 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 75.00 A   3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 5188 Count of symmetry unique reflns 2996 Completeness (_total/calc) 173.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2192 Fraction of Friedel pairs measured 0.732 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL004_ALERT_1_A The contact author's name and address are missing, _publ_contact_author_name and _publ_contact_author_address.
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 top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 2002). PLATON2002 (Spek, 2002); software used to prepare material for publication: SHELXL97.

(P)-4-(p-chlorophenyl)-3-{2-[4-(p- toluenesulfonyl)piperazino]ethoxy}thiazole-2(3H)-thione top
Crystal data top
C22H24ClN3O3S3Dx = 1.317 Mg m3
Mr = 510.07Melting point: not measured K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.227 (1) ÅCell parameters from 1846 reflections
b = 14.098 (1) Åθ = 3.2–16.9°
c = 22.178 (1) ŵ = 0.42 mm1
V = 2572.3 (4) Å3T = 299 K
Z = 4Needle, pale yellow
F(000) = 10640.30 × 0.12 × 0.06 mm
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
3163 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 26.4°, θmin = 4.2°
Detector resolution: Sapphire CCD detector pixels mm-1h = 105
Rotation method data acquisition using ω scansk = 1717
17136 measured reflectionsl = 2727
5188 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.0578P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.002
5188 reflectionsΔρmax = 0.30 e Å3
289 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (10)
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.

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
C20.0658 (5)0.8986 (3)0.0476 (2)0.0420 (11)
C40.1041 (5)0.9523 (3)0.0527 (2)0.0369 (10)
C50.0759 (5)1.0343 (3)0.02488 (19)0.0443 (12)
H50.07371.09260.04450.053*
C60.1448 (6)0.9363 (3)0.1168 (2)0.0419 (11)
C70.2635 (6)0.8733 (3)0.1348 (2)0.0492 (12)
H70.31540.83610.10600.059*
C80.3070 (7)0.8642 (4)0.1947 (2)0.0626 (15)
H80.38960.82280.20600.075*
C90.2273 (7)0.9166 (4)0.2370 (2)0.0609 (15)
C100.1074 (7)0.9784 (4)0.2206 (2)0.0674 (16)
H100.05381.01380.24990.081*
C110.0656 (6)0.9884 (3)0.1604 (2)0.0531 (13)
H110.01631.03050.14940.064*
C120.0313 (6)0.7413 (3)0.0490 (2)0.0455 (11)
H12A0.07900.77960.08070.055*
H12B0.10820.73700.01600.055*
C130.0092 (6)0.6439 (3)0.0724 (2)0.0470 (12)
H13A0.06590.62840.10460.056*
H13B0.11760.64540.08950.056*
C140.1323 (6)0.5773 (3)0.0179 (2)0.0428 (12)
H14A0.12300.63800.03820.051*
H14B0.23720.57510.00200.051*
C150.1221 (6)0.4985 (3)0.0636 (2)0.0469 (12)
H15A0.21120.50400.09210.056*
H15B0.02100.50360.08590.056*
C160.0008 (6)0.3963 (3)0.0118 (2)0.0526 (13)
H16A0.10600.39930.00780.063*
H16B0.00800.33570.03230.063*
C170.0155 (6)0.4765 (3)0.0568 (2)0.0507 (12)
H17A0.11980.47190.07700.061*
H17B0.06900.47100.08710.061*
C180.0003 (6)0.3006 (3)0.1264 (2)0.0433 (12)
C190.1398 (7)0.2558 (3)0.1087 (2)0.0572 (14)
H190.14900.23250.06960.069*
C200.2664 (7)0.2453 (4)0.1486 (3)0.0697 (16)
H200.36080.21450.13640.084*
C210.2546 (8)0.2802 (4)0.2074 (3)0.0723 (17)
C220.1139 (8)0.3254 (4)0.2239 (3)0.0724 (17)
H220.10410.34900.26290.087*
C230.0134 (7)0.3367 (4)0.1841 (2)0.0649 (15)
H230.10730.36820.19590.078*
C240.3947 (9)0.2654 (5)0.2513 (3)0.114 (3)
H24A0.41360.19870.25640.137*
H24B0.49100.29490.23560.137*
H24C0.36780.29330.28950.137*
N10.0026 (5)0.5684 (2)0.02704 (16)0.0439 (10)
N20.1298 (5)0.4057 (2)0.03331 (16)0.0401 (9)
N30.0964 (4)0.8774 (2)0.01098 (17)0.0411 (10)
O10.3072 (4)0.3344 (2)0.11068 (17)0.0652 (10)
O20.1646 (4)0.2324 (2)0.03656 (16)0.0629 (10)
O30.1217 (4)0.78351 (19)0.02831 (13)0.0418 (8)
S10.04417 (17)1.02049 (8)0.05131 (5)0.0527 (3)
S20.0501 (2)0.82381 (10)0.10476 (6)0.0623 (4)
S30.16517 (16)0.31286 (9)0.07595 (6)0.0501 (3)
Cl10.2808 (3)0.90619 (14)0.31204 (7)0.1169 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.038 (3)0.050 (3)0.038 (3)0.008 (2)0.002 (2)0.000 (2)
C40.033 (2)0.035 (3)0.043 (3)0.002 (2)0.001 (2)0.004 (2)
C50.052 (3)0.034 (3)0.046 (3)0.003 (2)0.003 (2)0.002 (2)
C60.051 (3)0.031 (2)0.044 (3)0.000 (2)0.004 (2)0.003 (2)
C70.054 (3)0.046 (3)0.048 (3)0.004 (3)0.003 (3)0.007 (2)
C80.077 (4)0.059 (3)0.052 (3)0.021 (3)0.019 (3)0.001 (3)
C90.084 (4)0.058 (3)0.041 (3)0.009 (3)0.013 (3)0.005 (3)
C100.097 (5)0.058 (3)0.047 (3)0.015 (3)0.005 (3)0.008 (3)
C110.062 (3)0.051 (3)0.047 (3)0.014 (3)0.006 (3)0.007 (2)
C120.043 (3)0.035 (2)0.059 (3)0.001 (2)0.009 (3)0.007 (2)
C130.058 (3)0.036 (2)0.047 (3)0.001 (2)0.004 (3)0.005 (2)
C140.043 (3)0.035 (3)0.050 (3)0.005 (2)0.006 (2)0.001 (2)
C150.057 (3)0.032 (2)0.052 (3)0.001 (2)0.006 (2)0.001 (2)
C160.057 (3)0.037 (3)0.064 (3)0.008 (2)0.008 (3)0.013 (2)
C170.064 (3)0.039 (3)0.049 (3)0.003 (2)0.010 (3)0.007 (2)
C180.056 (3)0.030 (2)0.044 (3)0.003 (2)0.005 (2)0.008 (2)
C190.067 (4)0.046 (3)0.059 (3)0.012 (3)0.004 (3)0.005 (3)
C200.062 (4)0.069 (4)0.078 (4)0.020 (3)0.014 (3)0.006 (3)
C210.088 (5)0.065 (4)0.064 (4)0.007 (4)0.025 (4)0.000 (3)
C220.103 (5)0.065 (4)0.049 (3)0.000 (4)0.002 (4)0.004 (3)
C230.078 (4)0.058 (3)0.058 (3)0.003 (3)0.008 (3)0.003 (3)
C240.134 (6)0.105 (6)0.104 (5)0.020 (5)0.062 (5)0.003 (4)
N10.055 (3)0.0258 (19)0.051 (2)0.0011 (18)0.005 (2)0.0051 (17)
N20.049 (2)0.0210 (18)0.050 (2)0.0004 (17)0.0056 (19)0.0002 (17)
N30.050 (3)0.030 (2)0.044 (2)0.0013 (18)0.0048 (19)0.0011 (17)
O10.045 (2)0.052 (2)0.098 (3)0.0026 (17)0.019 (2)0.020 (2)
O20.077 (2)0.0329 (19)0.078 (3)0.0072 (18)0.014 (2)0.0049 (17)
O30.0423 (18)0.0301 (17)0.053 (2)0.0008 (14)0.0038 (15)0.0016 (14)
S10.0673 (8)0.0435 (7)0.0473 (7)0.0018 (7)0.0037 (7)0.0059 (6)
S20.0835 (10)0.0586 (8)0.0449 (7)0.0101 (8)0.0010 (7)0.0087 (7)
S30.0505 (7)0.0332 (6)0.0666 (8)0.0023 (6)0.0026 (7)0.0041 (6)
Cl10.184 (2)0.1208 (14)0.0463 (9)0.0491 (15)0.0268 (12)0.0094 (9)
Geometric parameters (Å, º) top
C2—N31.356 (5)C15—N21.473 (5)
C2—S21.655 (5)C15—H15A0.9700
C2—S11.729 (5)C15—H15B0.9700
C4—C51.330 (6)C16—N21.474 (6)
C4—N31.405 (5)C16—C171.514 (6)
C4—C61.478 (6)C16—H16A0.9700
C5—S11.721 (4)C16—H16B0.9700
C5—H50.9300C17—N11.458 (5)
C6—C71.379 (6)C17—H17A0.9700
C6—C111.379 (6)C17—H17B0.9700
C7—C81.382 (7)C18—C191.367 (7)
C7—H70.9300C18—C231.382 (6)
C8—C91.363 (7)C18—S31.770 (4)
C8—H80.9300C19—C201.375 (7)
C9—C101.365 (7)C19—H190.9300
C9—Cl11.728 (5)C20—C211.397 (8)
C10—C111.387 (7)C20—H200.9300
C10—H100.9300C21—C221.371 (8)
C11—H110.9300C21—C241.523 (8)
C12—O31.466 (5)C22—C231.379 (8)
C12—C131.505 (6)C22—H220.9300
C12—H12A0.9700C23—H230.9300
C12—H12B0.9700C24—H24A0.9600
C13—N11.465 (5)C24—H24B0.9600
C13—H13A0.9700C24—H24C0.9600
C13—H13B0.9700N2—S31.641 (3)
C14—N11.466 (5)N3—O31.394 (4)
C14—C151.506 (6)O1—S31.432 (3)
C14—H14A0.9700O2—S31.432 (3)
C14—H14B0.9700
N3—C2—S2127.4 (4)N2—C16—H16A110.0
N3—C2—S1106.5 (3)C17—C16—H16A110.0
S2—C2—S1126.1 (3)N2—C16—H16B110.0
C5—C4—N3109.9 (4)C17—C16—H16B110.0
C5—C4—C6128.2 (4)H16A—C16—H16B108.4
N3—C4—C6121.9 (4)N1—C17—C16111.0 (4)
C4—C5—S1112.5 (3)N1—C17—H17A109.4
C4—C5—H5123.7C16—C17—H17A109.4
S1—C5—H5123.7N1—C17—H17B109.4
C7—C6—C11118.3 (4)C16—C17—H17B109.4
C7—C6—C4122.5 (4)H17A—C17—H17B108.0
C11—C6—C4119.1 (4)C19—C18—C23120.3 (5)
C6—C7—C8121.4 (5)C19—C18—S3120.6 (4)
C6—C7—H7119.3C23—C18—S3119.1 (4)
C8—C7—H7119.3C18—C19—C20120.1 (5)
C9—C8—C7119.1 (5)C18—C19—H19120.0
C9—C8—H8120.4C20—C19—H19120.0
C7—C8—H8120.4C19—C20—C21120.6 (6)
C8—C9—C10120.7 (5)C19—C20—H20119.7
C8—C9—Cl1119.6 (4)C21—C20—H20119.7
C10—C9—Cl1119.6 (4)C22—C21—C20118.2 (5)
C9—C10—C11120.0 (5)C22—C21—C24122.2 (6)
C9—C10—H10120.0C20—C21—C24119.7 (6)
C11—C10—H10120.0C21—C22—C23121.6 (5)
C6—C11—C10120.3 (5)C21—C22—H22119.2
C6—C11—H11119.8C23—C22—H22119.2
C10—C11—H11119.8C22—C23—C18119.3 (5)
O3—C12—C13106.7 (4)C22—C23—H23120.4
O3—C12—H12A110.4C18—C23—H23120.4
C13—C12—H12A110.4C21—C24—H24A109.5
O3—C12—H12B110.4C21—C24—H24B109.5
C13—C12—H12B110.4H24A—C24—H24B109.5
H12A—C12—H12B108.6C21—C24—H24C109.5
N1—C13—C12114.7 (4)H24A—C24—H24C109.5
N1—C13—H13A108.6H24B—C24—H24C109.5
C12—C13—H13A108.6C17—N1—C13109.4 (3)
N1—C13—H13B108.6C17—N1—C14109.3 (3)
C12—C13—H13B108.6C13—N1—C14112.2 (3)
H13A—C13—H13B107.6C15—N2—C16111.0 (3)
N1—C14—C15110.7 (4)C15—N2—S3116.9 (3)
N1—C14—H14A109.5C16—N2—S3116.7 (3)
C15—C14—H14A109.5C2—N3—O3120.1 (4)
N1—C14—H14B109.5C2—N3—C4118.2 (4)
C15—C14—H14B109.5O3—N3—C4121.7 (3)
H14A—C14—H14B108.1N3—O3—C12110.1 (3)
N2—C15—C14110.2 (4)C5—S1—C292.8 (2)
N2—C15—H15A109.6O1—S3—O2119.9 (2)
C14—C15—H15A109.6O1—S3—N2106.61 (19)
N2—C15—H15B109.6O2—S3—N2106.25 (19)
C14—C15—H15B109.6O1—S3—C18108.0 (2)
H15A—C15—H15B108.1O2—S3—C18107.8 (2)
N2—C16—C17108.4 (4)N2—S3—C18107.8 (2)
N3—C4—C5—S11.1 (5)C15—C14—N1—C1758.3 (5)
C6—C4—C5—S1176.5 (4)C15—C14—N1—C13179.9 (4)
C5—C4—C6—C7137.0 (5)C14—C15—N2—C1657.3 (5)
N3—C4—C6—C740.3 (6)C14—C15—N2—S3165.5 (3)
C5—C4—C6—C1140.7 (7)C17—C16—N2—C1557.8 (5)
N3—C4—C6—C11142.0 (4)C17—C16—N2—S3164.8 (3)
C11—C6—C7—C82.1 (7)S2—C2—N3—O31.2 (6)
C4—C6—C7—C8175.6 (4)S1—C2—N3—O3179.3 (3)
C6—C7—C8—C92.0 (8)S2—C2—N3—C4179.7 (3)
C7—C8—C9—C100.9 (8)S1—C2—N3—C40.2 (5)
C7—C8—C9—Cl1179.8 (4)C5—C4—N3—C20.9 (5)
C8—C9—C10—C110.0 (9)C6—C4—N3—C2176.9 (4)
Cl1—C9—C10—C11178.9 (4)C5—C4—N3—O3179.9 (4)
C7—C6—C11—C101.2 (7)C6—C4—N3—O32.1 (6)
C4—C6—C11—C10176.6 (4)C2—N3—O3—C1294.1 (4)
C9—C10—C11—C60.1 (8)C4—N3—O3—C1286.9 (4)
O3—C12—C13—N189.4 (5)C13—C12—O3—N3174.6 (3)
N1—C14—C15—N257.0 (5)C4—C5—S1—C20.9 (4)
N2—C16—C17—N159.7 (5)N3—C2—S1—C50.3 (3)
C23—C18—C19—C201.0 (7)S2—C2—S1—C5179.1 (3)
S3—C18—C19—C20178.9 (4)C15—N2—S3—O151.8 (4)
C18—C19—C20—C210.3 (8)C16—N2—S3—O1173.3 (3)
C19—C20—C21—C220.2 (9)C15—N2—S3—O2179.2 (3)
C19—C20—C21—C24178.4 (5)C16—N2—S3—O244.4 (4)
C20—C21—C22—C230.1 (9)C15—N2—S3—C1863.9 (4)
C24—C21—C22—C23178.7 (6)C16—N2—S3—C1871.0 (4)
C21—C22—C23—C180.8 (8)C19—C18—S3—O1162.3 (4)
C19—C18—C23—C221.3 (7)C23—C18—S3—O117.5 (4)
S3—C18—C23—C22178.6 (4)C19—C18—S3—O231.5 (4)
C16—C17—N1—C13176.6 (4)C23—C18—S3—O2148.4 (4)
C16—C17—N1—C1460.1 (5)C19—C18—S3—N282.8 (4)
C12—C13—N1—C17170.0 (4)C23—C18—S3—N297.3 (4)
C12—C13—N1—C1468.4 (5)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds