[4-(2,3-Dichloro­phen­yl)piperazin-1-yl][2-(2-methoxy­phenyl­sulfan­yl)phen­yl]methanone

In the title compound, C₂₄H₂₂Cl₂N₂O₂S, synthesized from 2-(2-methoxy­phenyl­sulfan­yl)benzoyl chloride and 1-(2,3-dichloro­phen­yl)piperazine, the piperazine ring adopts a normal chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.107
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
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Computing details

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.

[4-(2,3-Dichlorophenyl)piperazin-1-yl][2-(2- methoxyphenylsulfanyl)phenyl]methanone

Crystal data

C24H22Cl2N2O2S	F(000) = 984
Mr = 473.40	Dx = 1.412 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.034 (3) Å	Cell parameters from 2087 reflections
b = 7.6898 (14) Å	θ = 2.4–21.9°
c = 17.229 (3) Å	µ = 0.41 mm^−1
β = 99.344 (3)°	T = 294 K
V = 2226.9 (7) Å^3	Block, colorless
Z = 4	0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4587 independent reflections
Radiation source: fine-focus sealed tube	2529 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 26.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −21→19
Tmin = 0.900, Tmax = 0.921	k = −7→9
12169 measured reflections	l = −21→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.1467P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max = 0.003
S = 0.99	Δρmax = 0.22 e Å^−3
4587 reflections	Δρmin = −0.21 e Å^−3
282 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.34929 (4)	0.02950 (9)	0.03287 (4)	0.0472 (2)
Cl1	0.00184 (4)	0.40743 (11)	0.20221 (4)	0.0617 (3)
Cl2	−0.10471 (5)	0.69113 (12)	0.10512 (5)	0.0741 (3)
O1	0.24631 (11)	−0.0927 (3)	−0.09742 (10)	0.0551 (5)
O2	0.29077 (11)	−0.2025 (2)	0.18877 (11)	0.0544 (5)
N1	0.26497 (12)	0.0807 (3)	0.20887 (12)	0.0391 (5)
N2	0.16291 (12)	0.3634 (3)	0.15770 (12)	0.0400 (6)
C1	0.34761 (15)	−0.1893 (3)	0.00088 (15)	0.0375 (6)
C2	0.29192 (16)	−0.2292 (4)	−0.06588 (15)	0.0415 (7)
C3	0.28688 (19)	−0.3977 (4)	−0.09438 (16)	0.0541 (8)
H3	0.2496	−0.4249	−0.1384	0.065*
C4	0.3362 (2)	−0.5254 (4)	−0.05848 (17)	0.0624 (9)
H4	0.3324	−0.6381	−0.0783	0.075*
C5	0.3912 (2)	−0.4869 (4)	0.00660 (18)	0.0612 (9)
H5	0.4246	−0.5733	0.0310	0.073*
C6	0.39692 (17)	−0.3187 (4)	0.03577 (16)	0.0479 (7)
H6	0.4346	−0.2929	0.0796	0.057*
C7	0.18830 (18)	−0.1266 (4)	−0.16529 (16)	0.0648 (9)
H7A	0.2144	−0.1650	−0.2076	0.097*
H7B	0.1589	−0.0222	−0.1806	0.097*
H7C	0.1525	−0.2154	−0.1533	0.097*
C8	0.42141 (15)	0.0236 (3)	0.11991 (14)	0.0368 (6)
C9	0.50035 (17)	0.0597 (4)	0.11614 (17)	0.0474 (7)
H9	0.5157	0.0813	0.0677	0.057*
C10	0.55623 (17)	0.0638 (4)	0.18328 (18)	0.0520 (8)
H10	0.6092	0.0875	0.1802	0.062*
C11	0.53368 (16)	0.0328 (4)	0.25508 (17)	0.0477 (8)
H11	0.5715	0.0357	0.3005	0.057*
C12	0.45597 (16)	−0.0023 (3)	0.26019 (15)	0.0411 (7)
H12	0.4413	−0.0235	0.3090	0.049*
C13	0.39881 (14)	−0.0065 (3)	0.19291 (14)	0.0334 (6)
C14	0.31333 (15)	−0.0512 (4)	0.19698 (14)	0.0362 (6)
C15	0.17878 (15)	0.0583 (3)	0.19848 (16)	0.0425 (7)
H15A	0.1603	0.0800	0.2480	0.051*
H15B	0.1651	−0.0604	0.1826	0.051*
C16	0.13837 (15)	0.1828 (3)	0.13653 (15)	0.0425 (7)
H16A	0.1527	0.1536	0.0859	0.051*
H16B	0.0811	0.1723	0.1324	0.051*
C17	0.24925 (15)	0.3804 (3)	0.16169 (16)	0.0456 (7)
H17A	0.2654	0.4995	0.1740	0.055*
H17B	0.2640	0.3506	0.1113	0.055*
C18	0.29031 (16)	0.2604 (3)	0.22434 (17)	0.0490 (8)
H18A	0.3474	0.2685	0.2263	0.059*
H18B	0.2782	0.2960	0.2751	0.059*
C19	0.11593 (16)	0.4963 (3)	0.11632 (14)	0.0377 (7)
C20	0.14566 (18)	0.6062 (4)	0.06411 (16)	0.0509 (8)
H20	0.1972	0.5899	0.0540	0.061*
C21	0.0998 (2)	0.7396 (4)	0.02689 (17)	0.0590 (9)
H21	0.1212	0.8141	−0.0067	0.071*
C22	0.0230 (2)	0.7628 (4)	0.03910 (17)	0.0587 (9)
H22	−0.0083	0.8499	0.0124	0.070*
C23	−0.00755 (16)	0.6563 (4)	0.09105 (16)	0.0463 (7)
C24	0.03886 (16)	0.5262 (3)	0.13112 (14)	0.0412 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0574 (5)	0.0375 (4)	0.0431 (4)	0.0030 (4)	−0.0026 (3)	−0.0008 (4)
Cl1	0.0486 (5)	0.0746 (6)	0.0648 (5)	0.0047 (4)	0.0178 (4)	0.0180 (4)
Cl2	0.0577 (6)	0.0848 (7)	0.0774 (6)	0.0291 (5)	0.0040 (4)	−0.0028 (5)
O1	0.0572 (13)	0.0530 (13)	0.0492 (12)	0.0046 (10)	−0.0091 (10)	−0.0010 (10)
O2	0.0521 (13)	0.0280 (11)	0.0827 (15)	−0.0038 (10)	0.0097 (11)	0.0015 (10)
N1	0.0306 (13)	0.0322 (13)	0.0534 (14)	−0.0015 (10)	0.0036 (10)	−0.0028 (11)
N2	0.0341 (14)	0.0304 (12)	0.0541 (15)	−0.0041 (10)	0.0028 (11)	−0.0008 (11)
C1	0.0443 (17)	0.0341 (16)	0.0350 (15)	−0.0039 (13)	0.0091 (13)	0.0025 (13)
C2	0.0484 (18)	0.0415 (18)	0.0354 (16)	−0.0037 (14)	0.0096 (14)	0.0014 (14)
C3	0.072 (2)	0.048 (2)	0.0407 (17)	−0.0072 (17)	0.0046 (15)	−0.0037 (16)
C4	0.099 (3)	0.0386 (18)	0.051 (2)	−0.0008 (19)	0.0151 (19)	−0.0046 (16)
C5	0.085 (2)	0.041 (2)	0.058 (2)	0.0092 (17)	0.0106 (18)	0.0037 (17)
C6	0.059 (2)	0.0382 (18)	0.0439 (17)	−0.0013 (15)	0.0008 (14)	0.0023 (14)
C7	0.060 (2)	0.078 (2)	0.0501 (19)	−0.0023 (18)	−0.0091 (16)	−0.0002 (18)
C8	0.0409 (17)	0.0286 (14)	0.0399 (16)	−0.0016 (12)	0.0036 (13)	−0.0012 (12)
C9	0.0469 (19)	0.0486 (19)	0.0493 (18)	−0.0058 (15)	0.0157 (15)	−0.0089 (15)
C10	0.0367 (17)	0.051 (2)	0.070 (2)	−0.0034 (14)	0.0128 (16)	−0.0092 (17)
C11	0.0365 (18)	0.0486 (18)	0.0528 (19)	0.0085 (14)	−0.0082 (14)	−0.0100 (15)
C12	0.0420 (18)	0.0413 (17)	0.0394 (16)	0.0065 (13)	0.0044 (13)	−0.0011 (13)
C13	0.0334 (15)	0.0248 (14)	0.0416 (16)	0.0023 (11)	0.0046 (12)	−0.0031 (12)
C14	0.0390 (17)	0.0318 (16)	0.0360 (15)	−0.0011 (13)	0.0010 (12)	0.0029 (13)
C15	0.0363 (17)	0.0380 (16)	0.0529 (17)	−0.0017 (13)	0.0065 (13)	0.0030 (14)
C16	0.0373 (16)	0.0390 (17)	0.0496 (17)	−0.0064 (13)	0.0026 (13)	0.0027 (14)
C17	0.0330 (17)	0.0317 (16)	0.072 (2)	−0.0052 (13)	0.0091 (14)	−0.0077 (15)
C18	0.0356 (16)	0.0355 (17)	0.073 (2)	0.0005 (13)	−0.0010 (14)	−0.0151 (16)
C19	0.0420 (17)	0.0345 (16)	0.0352 (15)	−0.0004 (13)	0.0018 (13)	−0.0025 (13)
C20	0.055 (2)	0.0482 (19)	0.0503 (18)	−0.0024 (16)	0.0112 (15)	0.0037 (16)
C21	0.073 (2)	0.050 (2)	0.054 (2)	−0.0099 (18)	0.0100 (17)	0.0107 (16)
C22	0.073 (2)	0.0437 (19)	0.053 (2)	0.0062 (17)	−0.0108 (17)	0.0039 (16)
C23	0.0486 (19)	0.0432 (18)	0.0440 (17)	0.0028 (15)	−0.0022 (14)	−0.0053 (15)
C24	0.0433 (17)	0.0411 (16)	0.0377 (16)	0.0030 (14)	0.0021 (13)	0.0024 (14)

Geometric parameters (Å, º)

S1—C1	1.769 (3)	C9—C10	1.374 (4)
S1—C8	1.778 (3)	C9—H9	0.9300
Cl1—C24	1.727 (3)	C10—C11	1.374 (4)
Cl2—C23	1.732 (3)	C10—H10	0.9300
O1—C2	1.365 (3)	C11—C12	1.368 (3)
O1—C7	1.427 (3)	C11—H11	0.9300
O2—C14	1.226 (3)	C12—C13	1.388 (3)
N1—C14	1.343 (3)	C12—H12	0.9300
N1—C18	1.459 (3)	C13—C14	1.509 (3)
N1—C15	1.460 (3)	C15—C16	1.513 (3)
N2—C19	1.417 (3)	C15—H15A	0.9700
N2—C17	1.467 (3)	C15—H15B	0.9700
N2—C16	1.479 (3)	C16—H16A	0.9700
C1—C6	1.376 (4)	C16—H16B	0.9700
C1—C2	1.401 (3)	C17—C18	1.503 (4)
C2—C3	1.383 (4)	C17—H17A	0.9700
C3—C4	1.373 (4)	C17—H17B	0.9700
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.372 (4)	C18—H18B	0.9700
C4—H4	0.9300	C19—C20	1.389 (3)
C5—C6	1.385 (4)	C19—C24	1.396 (4)
C5—H5	0.9300	C20—C21	1.382 (4)
C6—H6	0.9300	C20—H20	0.9300
C7—H7A	0.9600	C21—C22	1.369 (4)
C7—H7B	0.9600	C21—H21	0.9300
C7—H7C	0.9600	C22—C23	1.376 (4)
C8—C9	1.385 (4)	C22—H22	0.9300
C8—C13	1.393 (3)	C23—C24	1.388 (4)
C1—S1—C8	102.28 (12)	C12—C13—C14	121.2 (2)
C2—O1—C7	117.4 (2)	C8—C13—C14	119.3 (2)
C14—N1—C18	124.9 (2)	O2—C14—N1	123.1 (2)
C14—N1—C15	121.4 (2)	O2—C14—C13	119.8 (2)
C18—N1—C15	113.3 (2)	N1—C14—C13	117.1 (2)
C19—N2—C17	116.1 (2)	N1—C15—C16	110.2 (2)
C19—N2—C16	116.1 (2)	N1—C15—H15A	109.6
C17—N2—C16	109.7 (2)	C16—C15—H15A	109.6
C6—C1—C2	118.9 (2)	N1—C15—H15B	109.6
C6—C1—S1	125.0 (2)	C16—C15—H15B	109.6
C2—C1—S1	116.0 (2)	H15A—C15—H15B	108.1
O1—C2—C3	125.5 (3)	N2—C16—C15	110.0 (2)
O1—C2—C1	115.1 (2)	N2—C16—H16A	109.7
C3—C2—C1	119.4 (3)	C15—C16—H16A	109.7
C4—C3—C2	120.8 (3)	N2—C16—H16B	109.7
C4—C3—H3	119.6	C15—C16—H16B	109.7
C2—C3—H3	119.6	H16A—C16—H16B	108.2
C5—C4—C3	120.1 (3)	N2—C17—C18	109.0 (2)
C5—C4—H4	120.0	N2—C17—H17A	109.9
C3—C4—H4	120.0	C18—C17—H17A	109.9
C4—C5—C6	119.8 (3)	N2—C17—H17B	109.9
C4—C5—H5	120.1	C18—C17—H17B	109.9
C6—C5—H5	120.1	H17A—C17—H17B	108.3
C1—C6—C5	121.0 (3)	N1—C18—C17	111.1 (2)
C1—C6—H6	119.5	N1—C18—H18A	109.4
C5—C6—H6	119.5	C17—C18—H18A	109.4
O1—C7—H7A	109.5	N1—C18—H18B	109.4
O1—C7—H7B	109.5	C17—C18—H18B	109.4
H7A—C7—H7B	109.5	H18A—C18—H18B	108.0
O1—C7—H7C	109.5	C20—C19—C24	118.1 (3)
H7A—C7—H7C	109.5	C20—C19—N2	122.0 (2)
H7B—C7—H7C	109.5	C24—C19—N2	119.9 (2)
C9—C8—C13	119.2 (2)	C21—C20—C19	120.9 (3)
C9—C8—S1	119.9 (2)	C21—C20—H20	119.5
C13—C8—S1	120.7 (2)	C19—C20—H20	119.5
C10—C9—C8	120.7 (3)	C22—C21—C20	120.5 (3)
C10—C9—H9	119.7	C22—C21—H21	119.8
C8—C9—H9	119.7	C20—C21—H21	119.8
C11—C10—C9	119.8 (3)	C21—C22—C23	119.6 (3)
C11—C10—H10	120.1	C21—C22—H22	120.2
C9—C10—H10	120.1	C23—C22—H22	120.2
C12—C11—C10	120.5 (3)	C22—C23—C24	120.5 (3)
C12—C11—H11	119.8	C22—C23—Cl2	118.1 (2)
C10—C11—H11	119.8	C24—C23—Cl2	121.5 (2)
C11—C12—C13	120.4 (2)	C23—C24—C19	120.3 (2)
C11—C12—H12	119.8	C23—C24—Cl1	119.3 (2)
C13—C12—H12	119.8	C19—C24—Cl1	120.3 (2)
C12—C13—C8	119.4 (2)
C8—S1—C1—C6	−4.3 (3)	C12—C13—C14—O2	−91.9 (3)
C8—S1—C1—C2	176.6 (2)	C8—C13—C14—O2	85.2 (3)
C7—O1—C2—C3	0.3 (4)	C12—C13—C14—N1	88.8 (3)
C7—O1—C2—C1	−179.7 (2)	C8—C13—C14—N1	−94.1 (3)
C6—C1—C2—O1	−179.0 (2)	C14—N1—C15—C16	−120.8 (3)
S1—C1—C2—O1	0.1 (3)	C18—N1—C15—C16	52.9 (3)
C6—C1—C2—C3	1.0 (4)	C19—N2—C16—C15	−165.1 (2)
S1—C1—C2—C3	−179.9 (2)	C17—N2—C16—C15	61.0 (3)
O1—C2—C3—C4	179.4 (3)	N1—C15—C16—N2	−55.7 (3)
C1—C2—C3—C4	−0.6 (4)	C19—N2—C17—C18	164.8 (2)
C2—C3—C4—C5	0.2 (5)	C16—N2—C17—C18	−61.2 (3)
C3—C4—C5—C6	−0.2 (5)	C14—N1—C18—C17	119.2 (3)
C2—C1—C6—C5	−1.0 (4)	C15—N1—C18—C17	−54.3 (3)
S1—C1—C6—C5	179.9 (2)	N2—C17—C18—N1	57.4 (3)
C4—C5—C6—C1	0.6 (5)	C17—N2—C19—C20	18.0 (3)
C1—S1—C8—C9	92.5 (2)	C16—N2—C19—C20	−113.0 (3)
C1—S1—C8—C13	−91.5 (2)	C17—N2—C19—C24	−158.1 (2)
C13—C8—C9—C10	0.8 (4)	C16—N2—C19—C24	70.9 (3)
S1—C8—C9—C10	176.9 (2)	C24—C19—C20—C21	−1.1 (4)
C8—C9—C10—C11	−0.3 (4)	N2—C19—C20—C21	−177.3 (2)
C9—C10—C11—C12	0.1 (4)	C19—C20—C21—C22	−1.9 (4)
C10—C11—C12—C13	−0.2 (4)	C20—C21—C22—C23	2.4 (4)
C11—C12—C13—C8	0.7 (4)	C21—C22—C23—C24	0.1 (4)
C11—C12—C13—C14	177.8 (2)	C21—C22—C23—Cl2	179.6 (2)
C9—C8—C13—C12	−0.9 (4)	C22—C23—C24—C19	−3.1 (4)
S1—C8—C13—C12	−177.03 (19)	Cl2—C23—C24—C19	177.4 (2)
C9—C8—C13—C14	−178.1 (2)	C22—C23—C24—Cl1	174.3 (2)
S1—C8—C13—C14	5.8 (3)	Cl2—C23—C24—Cl1	−5.2 (3)
C18—N1—C14—O2	175.5 (2)	C20—C19—C24—C23	3.5 (4)
C15—N1—C14—O2	−11.5 (4)	N2—C19—C24—C23	179.8 (2)
C18—N1—C14—C13	−5.2 (4)	C20—C19—C24—Cl1	−173.9 (2)
C15—N1—C14—C13	167.8 (2)	N2—C19—C24—Cl1	2.4 (3)