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The title compound, C25H26N2O3S, was synthesized from 2-(2-methoxy­phenyl­sulfan­yl)benzoic chloride and 1-(2-methoxy­phenyl)piperazine. The piperazine ring exhibits a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040845/sg6042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040845/sg6042Isup2.hkl
Contains datablock I

CCDC reference: 296646

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.117
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 .. 7.15 su
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.12 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 6.24 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 6.20 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Substituted diphenyl sulfide derivatives are a class of compounds which display high in vitro and in vivo affinities for SERT [Please define], high selectivity for dopamine transporter sites (DAT) and partial selectivity over norepinephrine transporter sites (NET), and have been described as potent and selective SERT ligands.

The title compound, (I), was synthesized from 2-(2-methoxyphenylsulfanyl)benzoic chloride and 1-(2-methoxyphenyl)piperazine. The molecular structure of the title compound is illustrated in Fig. 1. In the molecule, the piperazine ring is in a normal chair conformation.

Experimental top

2-(2-Methoxyphenylsulfanyl)benzoic chloride (8 mmol), triethylamine (20 mmol) and 1-(2-methoxyphenyl)piperazine (8 mmol) in CHCl3 (60 ml) were stirred at room temperature for 3–4.5 h. After cooling to room temperature, the mixture was washed with 2 M sodium hydroxide [Text missing] water. The organic layer was dried and evaporated in vacuo to dryness to give a sticky yellow oil, which solidified at room temperature. After recrystallization from 60% aqueous ethanol (50–70 ml), the title compound was obtained as a white crystalline solid. Crystals of (I) suitable for X-ray analysis were grown by slow evaporation of an absolute methanol solution at room temperature over 15 d.

Refinement top

All H atoms were positioned geometrically and refined as riding, with C—H distances in the range 0.93–0.98 Å and with Uiso(H) = 1.2 Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. The crystal structure of (I), viewed along the a axis
1-(2-Methoxyphenyl)-4-[2-(2-methoxyphenylsulfanyl)benzoyl]piperazine top
Crystal data top
C25H26N2O3SF(000) = 920
Mr = 434.54Dx = 1.260 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.483 (3) ÅCell parameters from 1945 reflections
b = 16.535 (3) Åθ = 2.2–21.5°
c = 12.504 (3) ŵ = 0.17 mm1
β = 117.451 (3)°T = 294 K
V = 2290.3 (8) Å3Block, colourless
Z = 40.40 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4695 independent reflections
Radiation source: fine-focus sealed tube2189 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ϕ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1515
Tmin = 0.935, Tmax = 0.983k = 1620
12787 measured reflectionsl = 1315
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.22 e Å3
4695 reflectionsΔρmin = 0.23 e Å3
282 parameters
Crystal data top
C25H26N2O3SV = 2290.3 (8) Å3
Mr = 434.54Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.483 (3) ŵ = 0.17 mm1
b = 16.535 (3) ÅT = 294 K
c = 12.504 (3) Å0.40 × 0.20 × 0.10 mm
β = 117.451 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4695 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2189 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.983Rint = 0.059
12787 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05112 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
4695 reflectionsΔρmin = 0.23 e Å3
282 parameters
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
S10.18655 (7)0.35402 (4)0.41319 (6)0.0619 (3)
O10.38091 (18)0.45819 (13)0.57576 (19)0.0805 (6)
O20.05884 (16)0.17435 (12)0.47387 (18)0.0748 (6)
O30.70832 (15)0.17154 (12)0.79722 (19)0.0721 (6)
N10.25815 (17)0.18300 (13)0.59192 (19)0.0539 (6)
N20.48832 (18)0.14815 (12)0.60888 (18)0.0517 (6)
C10.2188 (2)0.45255 (17)0.3826 (2)0.0508 (7)
C20.3159 (3)0.49610 (19)0.4694 (3)0.0621 (8)
C30.3393 (3)0.5744 (2)0.4431 (4)0.0917 (11)
H30.40150.60530.50050.110*
C40.2681 (4)0.6039 (2)0.3308 (5)0.1012 (13)
H40.28380.65580.31320.121*
C50.1759 (4)0.5628 (3)0.2431 (4)0.0982 (12)
H50.13080.58570.16740.118*
C60.1495 (3)0.4841 (2)0.2692 (3)0.0748 (9)
H60.08660.45420.21080.090*
C70.4652 (3)0.5053 (2)0.6751 (3)0.1250 (15)
H7A0.53140.52080.66060.187*
H7B0.49480.47380.74770.187*
H7C0.42570.55290.68370.187*
C80.1478 (2)0.36603 (15)0.5322 (2)0.0437 (6)
C90.1308 (2)0.44070 (16)0.5733 (2)0.0541 (7)
H90.14250.48790.53950.065*
C100.0968 (2)0.44560 (19)0.6633 (2)0.0616 (8)
H100.08640.49600.69040.074*
C110.0781 (2)0.3768 (2)0.7133 (2)0.0598 (8)
H110.05470.38020.77380.072*
C120.0944 (2)0.30215 (18)0.6733 (2)0.0527 (7)
H120.08020.25540.70620.063*
C130.13164 (19)0.29598 (15)0.5849 (2)0.0400 (6)
C140.1463 (2)0.21292 (16)0.5452 (2)0.0459 (7)
C150.2839 (2)0.10417 (15)0.5564 (2)0.0576 (8)
H15A0.21060.08190.49210.069*
H15B0.31220.06740.62440.069*
C160.3789 (2)0.11227 (16)0.5138 (2)0.0586 (8)
H16A0.39730.05940.49280.070*
H16B0.34850.14610.44240.070*
C170.4620 (2)0.22894 (16)0.6404 (3)0.0635 (8)
H17A0.43470.26420.57070.076*
H17B0.53510.25190.70410.076*
C180.3665 (2)0.22402 (17)0.6816 (3)0.0651 (9)
H18A0.39800.19480.75730.078*
H18B0.34540.27820.69520.078*
C190.5932 (2)0.14602 (15)0.5902 (3)0.0547 (7)
C200.5877 (3)0.12992 (18)0.4795 (3)0.0741 (9)
H200.51280.12200.41300.089*
C210.6920 (4)0.1253 (2)0.4652 (4)0.0926 (11)
H210.68680.11330.39030.111*
C220.8012 (3)0.1384 (2)0.5620 (4)0.0897 (11)
H220.87080.13630.55250.108*
C230.8102 (3)0.15496 (17)0.6737 (3)0.0719 (9)
H230.88560.16410.73880.086*
C240.7076 (2)0.15796 (16)0.6896 (3)0.0576 (8)
C250.8220 (2)0.18277 (19)0.9016 (3)0.0804 (10)
H25A0.87160.13590.91330.121*
H25B0.80910.19040.97100.121*
H25C0.86150.22950.89070.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0820 (6)0.0524 (5)0.0638 (5)0.0093 (4)0.0444 (4)0.0100 (4)
O10.0625 (13)0.0896 (16)0.0716 (15)0.0087 (13)0.0157 (12)0.0147 (13)
O20.0358 (11)0.0683 (14)0.0971 (15)0.0018 (10)0.0108 (11)0.0244 (11)
O30.0339 (11)0.0930 (16)0.0728 (14)0.0025 (10)0.0103 (11)0.0032 (12)
N10.0302 (12)0.0421 (14)0.0716 (16)0.0045 (11)0.0081 (12)0.0074 (11)
N20.0340 (12)0.0450 (14)0.0648 (15)0.0017 (11)0.0130 (12)0.0021 (11)
C10.0475 (17)0.0573 (19)0.0567 (19)0.0037 (15)0.0319 (16)0.0017 (15)
C20.060 (2)0.056 (2)0.082 (2)0.0062 (17)0.043 (2)0.0054 (18)
C30.097 (3)0.074 (3)0.136 (4)0.015 (2)0.081 (3)0.011 (2)
C40.118 (3)0.084 (3)0.134 (3)0.019 (2)0.086 (3)0.032 (2)
C50.095 (3)0.122 (3)0.103 (3)0.048 (2)0.068 (2)0.050 (2)
C60.073 (2)0.097 (3)0.074 (2)0.0236 (19)0.0502 (19)0.0310 (19)
C70.090 (3)0.159 (4)0.100 (3)0.020 (3)0.022 (2)0.062 (3)
C80.0372 (15)0.0446 (17)0.0445 (15)0.0004 (13)0.0146 (13)0.0013 (13)
C90.0598 (18)0.0457 (18)0.0617 (19)0.0014 (14)0.0323 (16)0.0024 (14)
C100.064 (2)0.060 (2)0.066 (2)0.0088 (16)0.0344 (17)0.0104 (16)
C110.0551 (19)0.081 (2)0.0486 (18)0.0132 (17)0.0282 (15)0.0046 (16)
C120.0432 (16)0.059 (2)0.0533 (18)0.0093 (14)0.0197 (14)0.0160 (14)
C130.0279 (14)0.0455 (17)0.0409 (15)0.0074 (12)0.0109 (12)0.0050 (12)
C140.0337 (15)0.0475 (17)0.0517 (17)0.0006 (14)0.0155 (14)0.0023 (13)
C150.0380 (16)0.0398 (17)0.079 (2)0.0015 (13)0.0135 (16)0.0002 (14)
C160.0493 (18)0.0422 (17)0.074 (2)0.0002 (14)0.0202 (16)0.0030 (14)
C170.0358 (15)0.0485 (19)0.087 (2)0.0010 (14)0.0115 (16)0.0095 (15)
C180.0334 (15)0.060 (2)0.080 (2)0.0041 (14)0.0079 (15)0.0164 (16)
C190.0472 (18)0.0436 (17)0.071 (2)0.0048 (14)0.0248 (17)0.0068 (15)
C200.068 (2)0.075 (2)0.079 (2)0.0004 (18)0.0343 (19)0.0033 (18)
C210.093 (3)0.100 (3)0.107 (3)0.001 (2)0.065 (3)0.007 (2)
C220.072 (3)0.084 (3)0.134 (4)0.010 (2)0.065 (3)0.020 (2)
C230.0467 (19)0.062 (2)0.108 (3)0.0025 (16)0.037 (2)0.0142 (19)
C240.0422 (18)0.0470 (18)0.080 (2)0.0034 (14)0.0250 (18)0.0085 (15)
C250.0399 (17)0.076 (2)0.090 (2)0.0071 (16)0.0001 (17)0.0018 (18)
Geometric parameters (Å, º) top
S1—C11.762 (3)C10—C111.369 (4)
S1—C81.776 (3)C10—H100.9300
O1—C21.351 (3)C11—C121.381 (4)
O1—C71.433 (3)C11—H110.9300
O2—C141.224 (3)C12—C131.387 (3)
O3—C241.360 (3)C12—H120.9300
O3—C251.429 (3)C13—C141.500 (3)
N1—C141.335 (3)C15—C161.513 (4)
N1—C151.460 (3)C15—H15A0.9700
N1—C181.466 (3)C15—H15B0.9700
N2—C191.432 (3)C16—H16A0.9700
N2—C161.461 (3)C16—H16B0.9700
N2—C171.472 (3)C17—C181.504 (4)
C1—C61.379 (3)C17—H17A0.9700
C1—C21.397 (4)C17—H17B0.9700
C2—C31.400 (4)C18—H18A0.9700
C3—C41.359 (5)C18—H18B0.9700
C3—H30.9300C19—C201.380 (4)
C4—C51.351 (5)C19—C241.410 (4)
C4—H40.9300C20—C211.396 (4)
C5—C61.417 (5)C20—H200.9300
C5—H50.9300C21—C221.360 (4)
C6—H60.9300C21—H210.9300
C7—H7A0.9600C22—C231.376 (4)
C7—H7B0.9600C22—H220.9300
C7—H7C0.9600C23—C241.384 (4)
C8—C91.390 (3)C23—H230.9300
C8—C131.392 (3)C25—H25A0.9600
C9—C101.377 (3)C25—H25B0.9600
C9—H90.9300C25—H25C0.9600
C1—S1—C8104.85 (12)O2—C14—N1121.8 (2)
C2—O1—C7118.0 (3)O2—C14—C13120.9 (2)
C24—O3—C25118.4 (2)N1—C14—C13117.2 (2)
C14—N1—C15122.0 (2)N1—C15—C16110.3 (2)
C14—N1—C18125.0 (2)N1—C15—H15A109.6
C15—N1—C18113.02 (19)C16—C15—H15A109.6
C19—N2—C16116.1 (2)N1—C15—H15B109.6
C19—N2—C17113.5 (2)C16—C15—H15B109.6
C16—N2—C17110.25 (19)H15A—C15—H15B108.1
C6—C1—C2120.8 (3)N2—C16—C15109.9 (2)
C6—C1—S1118.4 (2)N2—C16—H16A109.7
C2—C1—S1120.7 (2)C15—C16—H16A109.7
O1—C2—C1116.0 (3)N2—C16—H16B109.7
O1—C2—C3124.4 (3)C15—C16—H16B109.7
C1—C2—C3119.6 (3)H16A—C16—H16B108.2
C4—C3—C2117.8 (4)N2—C17—C18110.6 (2)
C4—C3—H3121.1N2—C17—H17A109.5
C2—C3—H3121.1C18—C17—H17A109.5
C5—C4—C3124.4 (4)N2—C17—H17B109.5
C5—C4—H4117.8C18—C17—H17B109.5
C3—C4—H4117.8H17A—C17—H17B108.1
C4—C5—C6118.5 (4)N1—C18—C17111.1 (2)
C4—C5—H5120.8N1—C18—H18A109.4
C6—C5—H5120.8C17—C18—H18A109.4
C1—C6—C5118.8 (3)N1—C18—H18B109.4
C1—C6—H6120.6C17—C18—H18B109.4
C5—C6—H6120.6H18A—C18—H18B108.0
O1—C7—H7A109.5C20—C19—C24118.2 (3)
O1—C7—H7B109.5C20—C19—N2122.8 (3)
H7A—C7—H7B109.5C24—C19—N2119.0 (3)
O1—C7—H7C109.5C19—C20—C21121.4 (3)
H7A—C7—H7C109.5C19—C20—H20119.3
H7B—C7—H7C109.5C21—C20—H20119.3
C9—C8—C13119.0 (2)C22—C21—C20119.3 (4)
C9—C8—S1123.8 (2)C22—C21—H21120.4
C13—C8—S1117.3 (2)C20—C21—H21120.4
C10—C9—C8120.7 (3)C21—C22—C23121.0 (3)
C10—C9—H9119.6C21—C22—H22119.5
C8—C9—H9119.6C23—C22—H22119.5
C11—C10—C9120.4 (3)C22—C23—C24120.3 (3)
C11—C10—H10119.8C22—C23—H23119.8
C9—C10—H10119.8C24—C23—H23119.8
C10—C11—C12119.6 (3)O3—C24—C23124.3 (3)
C10—C11—H11120.2O3—C24—C19115.9 (3)
C12—C11—H11120.2C23—C24—C19119.8 (3)
C11—C12—C13120.9 (3)O3—C25—H25A109.5
C11—C12—H12119.6O3—C25—H25B109.5
C13—C12—H12119.6H25A—C25—H25B109.5
C12—C13—C8119.4 (2)O3—C25—H25C109.5
C12—C13—C14117.9 (2)H25A—C25—H25C109.5
C8—C13—C14122.6 (2)H25B—C25—H25C109.5
C8—S1—C1—C6119.1 (2)C12—C13—C14—O279.7 (3)
C8—S1—C1—C263.9 (2)C8—C13—C14—O296.9 (3)
C7—O1—C2—C1167.7 (2)C12—C13—C14—N199.6 (3)
C7—O1—C2—C311.7 (4)C8—C13—C14—N183.7 (3)
C6—C1—C2—O1177.2 (2)C14—N1—C15—C16125.4 (2)
S1—C1—C2—O10.3 (3)C18—N1—C15—C1654.3 (3)
C6—C1—C2—C33.4 (4)C19—N2—C16—C15169.0 (2)
S1—C1—C2—C3179.7 (2)C17—N2—C16—C1560.1 (3)
O1—C2—C3—C4178.2 (3)N1—C15—C16—N257.5 (3)
C1—C2—C3—C42.4 (4)C19—N2—C17—C18169.2 (2)
C2—C3—C4—C50.3 (6)C16—N2—C17—C1858.6 (3)
C3—C4—C5—C60.9 (6)C14—N1—C18—C17126.8 (3)
C2—C1—C6—C52.1 (4)C15—N1—C18—C1752.9 (3)
S1—C1—C6—C5179.1 (2)N2—C17—C18—N154.2 (3)
C4—C5—C6—C10.0 (5)C16—N2—C19—C2015.3 (4)
C1—S1—C8—C98.8 (2)C17—N2—C19—C20114.0 (3)
C1—S1—C8—C13172.54 (18)C16—N2—C19—C24162.3 (2)
C13—C8—C9—C100.9 (4)C17—N2—C19—C2468.3 (3)
S1—C8—C9—C10177.78 (19)C24—C19—C20—C210.1 (4)
C8—C9—C10—C110.6 (4)N2—C19—C20—C21177.6 (3)
C9—C10—C11—C120.4 (4)C19—C20—C21—C221.3 (5)
C10—C11—C12—C131.3 (4)C20—C21—C22—C231.0 (5)
C11—C12—C13—C82.8 (3)C21—C22—C23—C240.4 (5)
C11—C12—C13—C14179.5 (2)C25—O3—C24—C230.6 (4)
C9—C8—C13—C122.5 (3)C25—O3—C24—C19179.0 (2)
S1—C8—C13—C12176.23 (17)C22—C23—C24—O3178.0 (3)
C9—C8—C13—C14179.1 (2)C22—C23—C24—C191.6 (4)
S1—C8—C13—C140.3 (3)C20—C19—C24—O3178.3 (2)
C15—N1—C14—O23.1 (4)N2—C19—C24—O30.6 (3)
C18—N1—C14—O2177.2 (3)C20—C19—C24—C231.3 (4)
C15—N1—C14—C13177.5 (2)N2—C19—C24—C23179.1 (2)
C18—N1—C14—C132.1 (4)

Experimental details

Crystal data
Chemical formulaC25H26N2O3S
Mr434.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)12.483 (3), 16.535 (3), 12.504 (3)
β (°) 117.451 (3)
V3)2290.3 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.935, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
12787, 4695, 2189
Rint0.059
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.117, 1.03
No. of reflections4695
No. of parameters282
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.23

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

 

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