1-(2-Methoxy­phen­yl)-4-[2-(2-methoxy­phenylsulfan­yl)benzo­yl]piperazine

Li, A.-J.; Tao, M.-L.; Ma, J.; Zhou, X.-Q.; Liu, D.-Z.

doi:10.1107/S1600536805040845

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1-(2-Methoxyphenyl)-4-[2-(2-methoxyphenylsulfanyl)benzoyl]piperazine

A.-J. Li, M.-L. Tao, J. Ma, X.-Q. Zhou and D.-Z. Liu

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

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040845/sg6042sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040845/sg6042Isup2.hkl Contains datablock I

CCDC reference: 296646

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (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.

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

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	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

C₂₅H₂₆N₂O₃S	F(000) = 920
M_r = 434.54	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.483 (3) Å	Cell parameters from 1945 reflections
b = 16.535 (3) Å	θ = 2.2–21.5°
c = 12.504 (3) Å	µ = 0.17 mm⁻¹
β = 117.451 (3)°	T = 294 K
V = 2290.3 (8) Å³	Block, colourless
Z = 4	0.40 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4695 independent reflections
Radiation source: fine-focus sealed tube	2189 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→15
T_min = 0.935, T_max = 0.983	k = −16→20
12787 measured reflections	l = −13→15

Refinement top

Refinement on F²	12 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.04P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.22 e Å⁻³
4695 reflections	Δρ_min = −0.23 e Å⁻³
282 parameters

Crystal data top

C₂₅H₂₆N₂O₃S	V = 2290.3 (8) Å³
M_r = 434.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.483 (3) Å	µ = 0.17 mm⁻¹
b = 16.535 (3) Å	T = 294 K
c = 12.504 (3) Å	0.40 × 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)
T_min = 0.935, T_max = 0.983	R_int = 0.059
12787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	12 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
4695 reflections	Δρ_min = −0.23 e Å⁻³
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

	x	y	z	U_iso*/U_eq
S1	0.18655 (7)	0.35402 (4)	0.41319 (6)	0.0619 (3)
O1	0.38091 (18)	0.45819 (13)	0.57576 (19)	0.0805 (6)
O2	0.05884 (16)	0.17435 (12)	0.47387 (18)	0.0748 (6)
O3	0.70832 (15)	0.17154 (12)	0.79722 (19)	0.0721 (6)
N1	0.25815 (17)	0.18300 (13)	0.59192 (19)	0.0539 (6)
N2	0.48832 (18)	0.14815 (12)	0.60888 (18)	0.0517 (6)
C1	0.2188 (2)	0.45255 (17)	0.3826 (2)	0.0508 (7)
C2	0.3159 (3)	0.49610 (19)	0.4694 (3)	0.0621 (8)
C3	0.3393 (3)	0.5744 (2)	0.4431 (4)	0.0917 (11)
H3	0.4015	0.6053	0.5005	0.110*
C4	0.2681 (4)	0.6039 (2)	0.3308 (5)	0.1012 (13)
H4	0.2838	0.6558	0.3132	0.121*
C5	0.1759 (4)	0.5628 (3)	0.2431 (4)	0.0982 (12)
H5	0.1308	0.5857	0.1674	0.118*
C6	0.1495 (3)	0.4841 (2)	0.2692 (3)	0.0748 (9)
H6	0.0866	0.4542	0.2108	0.090*
C7	0.4652 (3)	0.5053 (2)	0.6751 (3)	0.1250 (15)
H7A	0.5314	0.5208	0.6606	0.187*
H7B	0.4948	0.4738	0.7477	0.187*
H7C	0.4257	0.5529	0.6837	0.187*
C8	0.1478 (2)	0.36603 (15)	0.5322 (2)	0.0437 (6)
C9	0.1308 (2)	0.44070 (16)	0.5733 (2)	0.0541 (7)
H9	0.1425	0.4879	0.5395	0.065*
C10	0.0968 (2)	0.44560 (19)	0.6633 (2)	0.0616 (8)
H10	0.0864	0.4960	0.6904	0.074*
C11	0.0781 (2)	0.3768 (2)	0.7133 (2)	0.0598 (8)
H11	0.0547	0.3802	0.7738	0.072*
C12	0.0944 (2)	0.30215 (18)	0.6733 (2)	0.0527 (7)
H12	0.0802	0.2554	0.7062	0.063*
C13	0.13164 (19)	0.29598 (15)	0.5849 (2)	0.0400 (6)
C14	0.1463 (2)	0.21292 (16)	0.5452 (2)	0.0459 (7)
C15	0.2839 (2)	0.10417 (15)	0.5564 (2)	0.0576 (8)
H15A	0.2106	0.0819	0.4921	0.069*
H15B	0.3122	0.0674	0.6244	0.069*
C16	0.3789 (2)	0.11227 (16)	0.5138 (2)	0.0586 (8)
H16A	0.3973	0.0594	0.4928	0.070*
H16B	0.3485	0.1461	0.4424	0.070*
C17	0.4620 (2)	0.22894 (16)	0.6404 (3)	0.0635 (8)
H17A	0.4347	0.2642	0.5707	0.076*
H17B	0.5351	0.2519	0.7041	0.076*
C18	0.3665 (2)	0.22402 (17)	0.6816 (3)	0.0651 (9)
H18A	0.3980	0.1948	0.7573	0.078*
H18B	0.3454	0.2782	0.6952	0.078*
C19	0.5932 (2)	0.14602 (15)	0.5902 (3)	0.0547 (7)
C20	0.5877 (3)	0.12992 (18)	0.4795 (3)	0.0741 (9)
H20	0.5128	0.1220	0.4130	0.089*
C21	0.6920 (4)	0.1253 (2)	0.4652 (4)	0.0926 (11)
H21	0.6868	0.1133	0.3903	0.111*
C22	0.8012 (3)	0.1384 (2)	0.5620 (4)	0.0897 (11)
H22	0.8708	0.1363	0.5525	0.108*
C23	0.8102 (3)	0.15496 (17)	0.6737 (3)	0.0719 (9)
H23	0.8856	0.1641	0.7388	0.086*
C24	0.7076 (2)	0.15796 (16)	0.6896 (3)	0.0576 (8)
C25	0.8220 (2)	0.18277 (19)	0.9016 (3)	0.0804 (10)
H25A	0.8716	0.1359	0.9133	0.121*
H25B	0.8091	0.1904	0.9710	0.121*
H25C	0.8615	0.2295	0.8907	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0820 (6)	0.0524 (5)	0.0638 (5)	−0.0093 (4)	0.0444 (4)	−0.0100 (4)
O1	0.0625 (13)	0.0896 (16)	0.0716 (15)	−0.0087 (13)	0.0157 (12)	−0.0147 (13)
O2	0.0358 (11)	0.0683 (14)	0.0971 (15)	−0.0018 (10)	0.0108 (11)	−0.0244 (11)
O3	0.0339 (11)	0.0930 (16)	0.0728 (14)	−0.0025 (10)	0.0103 (11)	−0.0032 (12)
N1	0.0302 (12)	0.0421 (14)	0.0716 (16)	0.0045 (11)	0.0081 (12)	−0.0074 (11)
N2	0.0340 (12)	0.0450 (14)	0.0648 (15)	0.0017 (11)	0.0130 (12)	−0.0021 (11)
C1	0.0475 (17)	0.0573 (19)	0.0567 (19)	0.0037 (15)	0.0319 (16)	0.0017 (15)
C2	0.060 (2)	0.056 (2)	0.082 (2)	0.0062 (17)	0.043 (2)	0.0054 (18)
C3	0.097 (3)	0.074 (3)	0.136 (4)	−0.015 (2)	0.081 (3)	−0.011 (2)
C4	0.118 (3)	0.084 (3)	0.134 (3)	0.019 (2)	0.086 (3)	0.032 (2)
C5	0.095 (3)	0.122 (3)	0.103 (3)	0.048 (2)	0.068 (2)	0.050 (2)
C6	0.073 (2)	0.097 (3)	0.074 (2)	0.0236 (19)	0.0502 (19)	0.0310 (19)
C7	0.090 (3)	0.159 (4)	0.100 (3)	−0.020 (3)	0.022 (2)	−0.062 (3)
C8	0.0372 (15)	0.0446 (17)	0.0445 (15)	−0.0004 (13)	0.0146 (13)	−0.0013 (13)
C9	0.0598 (18)	0.0457 (18)	0.0617 (19)	0.0014 (14)	0.0323 (16)	−0.0024 (14)
C10	0.064 (2)	0.060 (2)	0.066 (2)	0.0088 (16)	0.0344 (17)	−0.0104 (16)
C11	0.0551 (19)	0.081 (2)	0.0486 (18)	0.0132 (17)	0.0282 (15)	0.0046 (16)
C12	0.0432 (16)	0.059 (2)	0.0533 (18)	0.0093 (14)	0.0197 (14)	0.0160 (14)
C13	0.0279 (14)	0.0455 (17)	0.0409 (15)	0.0074 (12)	0.0109 (12)	0.0050 (12)
C14	0.0337 (15)	0.0475 (17)	0.0517 (17)	0.0006 (14)	0.0155 (14)	0.0023 (13)
C15	0.0380 (16)	0.0398 (17)	0.079 (2)	0.0015 (13)	0.0135 (16)	0.0002 (14)
C16	0.0493 (18)	0.0422 (17)	0.074 (2)	−0.0002 (14)	0.0202 (16)	−0.0030 (14)
C17	0.0358 (15)	0.0485 (19)	0.087 (2)	0.0010 (14)	0.0115 (16)	−0.0095 (15)
C18	0.0334 (15)	0.060 (2)	0.080 (2)	0.0041 (14)	0.0079 (15)	−0.0164 (16)
C19	0.0472 (18)	0.0436 (17)	0.071 (2)	0.0048 (14)	0.0248 (17)	0.0068 (15)
C20	0.068 (2)	0.075 (2)	0.079 (2)	0.0004 (18)	0.0343 (19)	0.0033 (18)
C21	0.093 (3)	0.100 (3)	0.107 (3)	0.001 (2)	0.065 (3)	0.007 (2)
C22	0.072 (3)	0.084 (3)	0.134 (4)	0.010 (2)	0.065 (3)	0.020 (2)
C23	0.0467 (19)	0.062 (2)	0.108 (3)	0.0025 (16)	0.037 (2)	0.0142 (19)
C24	0.0422 (18)	0.0470 (18)	0.080 (2)	0.0034 (14)	0.0250 (18)	0.0085 (15)
C25	0.0399 (17)	0.076 (2)	0.090 (2)	−0.0071 (16)	−0.0001 (17)	0.0018 (18)

Geometric parameters (Å, º) top

S1—C1	1.762 (3)	C10—C11	1.369 (4)
S1—C8	1.776 (3)	C10—H10	0.9300
O1—C2	1.351 (3)	C11—C12	1.381 (4)
O1—C7	1.433 (3)	C11—H11	0.9300
O2—C14	1.224 (3)	C12—C13	1.387 (3)
O3—C24	1.360 (3)	C12—H12	0.9300
O3—C25	1.429 (3)	C13—C14	1.500 (3)
N1—C14	1.335 (3)	C15—C16	1.513 (4)
N1—C15	1.460 (3)	C15—H15A	0.9700
N1—C18	1.466 (3)	C15—H15B	0.9700
N2—C19	1.432 (3)	C16—H16A	0.9700
N2—C16	1.461 (3)	C16—H16B	0.9700
N2—C17	1.472 (3)	C17—C18	1.504 (4)
C1—C6	1.379 (3)	C17—H17A	0.9700
C1—C2	1.397 (4)	C17—H17B	0.9700
C2—C3	1.400 (4)	C18—H18A	0.9700
C3—C4	1.359 (5)	C18—H18B	0.9700
C3—H3	0.9300	C19—C20	1.380 (4)
C4—C5	1.351 (5)	C19—C24	1.410 (4)
C4—H4	0.9300	C20—C21	1.396 (4)
C5—C6	1.417 (5)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.360 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—H7A	0.9600	C22—C23	1.376 (4)
C7—H7B	0.9600	C22—H22	0.9300
C7—H7C	0.9600	C23—C24	1.384 (4)
C8—C9	1.390 (3)	C23—H23	0.9300
C8—C13	1.392 (3)	C25—H25A	0.9600
C9—C10	1.377 (3)	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600

C1—S1—C8	104.85 (12)	O2—C14—N1	121.8 (2)
C2—O1—C7	118.0 (3)	O2—C14—C13	120.9 (2)
C24—O3—C25	118.4 (2)	N1—C14—C13	117.2 (2)
C14—N1—C15	122.0 (2)	N1—C15—C16	110.3 (2)
C14—N1—C18	125.0 (2)	N1—C15—H15A	109.6
C15—N1—C18	113.02 (19)	C16—C15—H15A	109.6
C19—N2—C16	116.1 (2)	N1—C15—H15B	109.6
C19—N2—C17	113.5 (2)	C16—C15—H15B	109.6
C16—N2—C17	110.25 (19)	H15A—C15—H15B	108.1
C6—C1—C2	120.8 (3)	N2—C16—C15	109.9 (2)
C6—C1—S1	118.4 (2)	N2—C16—H16A	109.7
C2—C1—S1	120.7 (2)	C15—C16—H16A	109.7
O1—C2—C1	116.0 (3)	N2—C16—H16B	109.7
O1—C2—C3	124.4 (3)	C15—C16—H16B	109.7
C1—C2—C3	119.6 (3)	H16A—C16—H16B	108.2
C4—C3—C2	117.8 (4)	N2—C17—C18	110.6 (2)
C4—C3—H3	121.1	N2—C17—H17A	109.5
C2—C3—H3	121.1	C18—C17—H17A	109.5
C5—C4—C3	124.4 (4)	N2—C17—H17B	109.5
C5—C4—H4	117.8	C18—C17—H17B	109.5
C3—C4—H4	117.8	H17A—C17—H17B	108.1
C4—C5—C6	118.5 (4)	N1—C18—C17	111.1 (2)
C4—C5—H5	120.8	N1—C18—H18A	109.4
C6—C5—H5	120.8	C17—C18—H18A	109.4
C1—C6—C5	118.8 (3)	N1—C18—H18B	109.4
C1—C6—H6	120.6	C17—C18—H18B	109.4
C5—C6—H6	120.6	H18A—C18—H18B	108.0
O1—C7—H7A	109.5	C20—C19—C24	118.2 (3)
O1—C7—H7B	109.5	C20—C19—N2	122.8 (3)
H7A—C7—H7B	109.5	C24—C19—N2	119.0 (3)
O1—C7—H7C	109.5	C19—C20—C21	121.4 (3)
H7A—C7—H7C	109.5	C19—C20—H20	119.3
H7B—C7—H7C	109.5	C21—C20—H20	119.3
C9—C8—C13	119.0 (2)	C22—C21—C20	119.3 (4)
C9—C8—S1	123.8 (2)	C22—C21—H21	120.4
C13—C8—S1	117.3 (2)	C20—C21—H21	120.4
C10—C9—C8	120.7 (3)	C21—C22—C23	121.0 (3)
C10—C9—H9	119.6	C21—C22—H22	119.5
C8—C9—H9	119.6	C23—C22—H22	119.5
C11—C10—C9	120.4 (3)	C22—C23—C24	120.3 (3)
C11—C10—H10	119.8	C22—C23—H23	119.8
C9—C10—H10	119.8	C24—C23—H23	119.8
C10—C11—C12	119.6 (3)	O3—C24—C23	124.3 (3)
C10—C11—H11	120.2	O3—C24—C19	115.9 (3)
C12—C11—H11	120.2	C23—C24—C19	119.8 (3)
C11—C12—C13	120.9 (3)	O3—C25—H25A	109.5
C11—C12—H12	119.6	O3—C25—H25B	109.5
C13—C12—H12	119.6	H25A—C25—H25B	109.5
C12—C13—C8	119.4 (2)	O3—C25—H25C	109.5
C12—C13—C14	117.9 (2)	H25A—C25—H25C	109.5
C8—C13—C14	122.6 (2)	H25B—C25—H25C	109.5

C8—S1—C1—C6	−119.1 (2)	C12—C13—C14—O2	79.7 (3)
C8—S1—C1—C2	63.9 (2)	C8—C13—C14—O2	−96.9 (3)
C7—O1—C2—C1	−167.7 (2)	C12—C13—C14—N1	−99.6 (3)
C7—O1—C2—C3	11.7 (4)	C8—C13—C14—N1	83.7 (3)
C6—C1—C2—O1	−177.2 (2)	C14—N1—C15—C16	125.4 (2)
S1—C1—C2—O1	−0.3 (3)	C18—N1—C15—C16	−54.3 (3)
C6—C1—C2—C3	3.4 (4)	C19—N2—C16—C15	169.0 (2)
S1—C1—C2—C3	−179.7 (2)	C17—N2—C16—C15	−60.1 (3)
O1—C2—C3—C4	178.2 (3)	N1—C15—C16—N2	57.5 (3)
C1—C2—C3—C4	−2.4 (4)	C19—N2—C17—C18	−169.2 (2)
C2—C3—C4—C5	0.3 (6)	C16—N2—C17—C18	58.6 (3)
C3—C4—C5—C6	0.9 (6)	C14—N1—C18—C17	−126.8 (3)
C2—C1—C6—C5	−2.1 (4)	C15—N1—C18—C17	52.9 (3)
S1—C1—C6—C5	−179.1 (2)	N2—C17—C18—N1	−54.2 (3)
C4—C5—C6—C1	0.0 (5)	C16—N2—C19—C20	15.3 (4)
C1—S1—C8—C9	8.8 (2)	C17—N2—C19—C20	−114.0 (3)
C1—S1—C8—C13	−172.54 (18)	C16—N2—C19—C24	−162.3 (2)
C13—C8—C9—C10	−0.9 (4)	C17—N2—C19—C24	68.3 (3)
S1—C8—C9—C10	177.78 (19)	C24—C19—C20—C21	0.1 (4)
C8—C9—C10—C11	−0.6 (4)	N2—C19—C20—C21	−177.6 (3)
C9—C10—C11—C12	0.4 (4)	C19—C20—C21—C22	−1.3 (5)
C10—C11—C12—C13	1.3 (4)	C20—C21—C22—C23	1.0 (5)
C11—C12—C13—C8	−2.8 (3)	C21—C22—C23—C24	0.4 (5)
C11—C12—C13—C14	−179.5 (2)	C25—O3—C24—C23	−0.6 (4)
C9—C8—C13—C12	2.5 (3)	C25—O3—C24—C19	179.0 (2)
S1—C8—C13—C12	−176.23 (17)	C22—C23—C24—O3	178.0 (3)
C9—C8—C13—C14	179.1 (2)	C22—C23—C24—C19	−1.6 (4)
S1—C8—C13—C14	0.3 (3)	C20—C19—C24—O3	−178.3 (2)
C15—N1—C14—O2	3.1 (4)	N2—C19—C24—O3	−0.6 (3)
C18—N1—C14—O2	−177.2 (3)	C20—C19—C24—C23	1.3 (4)
C15—N1—C14—C13	−177.5 (2)	N2—C19—C24—C23	179.1 (2)
C18—N1—C14—C13	2.1 (4)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂O₃S
M_r	434.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	12.483 (3), 16.535 (3), 12.504 (3)
β (°)	117.451 (3)
V (Å³)	2290.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.935, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	12787, 4695, 2189
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.117, 1.03
No. of reflections	4695
No. of parameters	282
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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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