1,4-Ditosyl-1,4-diazepane

Yang, S.-H.; Zhai, Z.-W.

doi:10.1107/S1600536812020958

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1716

doi:10.1107/S1600536812020958

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1,4-Ditosyl-1,4-diazepane

Shuang-Hua Yang ^a and Zhi-Wei Zhai ^a ^*

^aDepartment of Environment Engineering and Chemistry, Luoyang Institute of Science and Technology, Luoyang 471023, People's Republic of China
^*Correspondence e-mail: zhaizw2005@126.com

(Received 20 April 2012; accepted 8 May 2012; online 12 May 2012)

In the title compound, C₁₉H₂₄N₂O₄S₂, the dihedral angle formed by the benzene rings is 82.88 (7)°, and the molecular conformation is enforced by weak intramolecular C—H⋯O contacts. Two C atoms of the 1,4-diazepane ring are disordered over two sets of sites with a refined occupancy ratio of 0.534 (13):0.466 (13). In the crystal, molecules are linked by weak intermolecular C—H⋯O interactions into chains parallel to the a axis.

Related literature

For related structures, see: Romba et al. (2002 ). For the biological activity of heterocyclic compounds, see: Xu et al. (2006 ); Yu et al. (2009 ).

Experimental

Crystal data

C₁₉H₂₄N₂O₄S₂
M_r = 408.52
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.3407 (13) Å
b = 10.367 (2) Å
c = 30.516 (6) Å
V = 2005.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 K
0.20 × 0.20 × 0.10 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.944, T_max = 0.971
11747 measured reflections
3531 independent reflections
3430 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.083
S = 1.07
3531 reflections
265 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1442 Friedel pairs
Flack parameter: −0.03 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O3	0.97	2.40	2.886 (3)	110
C12—H12A⋯O1	0.97	2.39	2.878 (3)	111
C10—H10B⋯O4ⁱ	0.97	2.52	3.142 (3)	122
C12—H12A⋯O2ⁱ	0.97	2.50	3.035 (3)	115
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020958/rz2746sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020958/rz2746Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020958/rz2746Isup3.cml

checkCIF report

Comment top

Many heterocyclic compounds have been widely used as potent and broad-spectrum fungicides (Xu et al., 2006; Yu et al., 2009). In order to search for new heterocylic compounds with higher biological activities, we synthesized the title compound and describe its structure herein.

In title compound (Fig. 1), all bond lengths are normal and in a good agreement with those reported for related compounds (Romba et al., 2002). Two atoms (C8 and C9) of the 1,4-diazepane ring are disordered over two orientations with refined occupancy ratio of 0.466 (13)/0.534 (13). The dihedral angle formed by the phenyl rings is 82.88 (7)°. The molecular conformation is stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonds to form chains parallel to the a axis.

Related literature top

For related structures, see: Romba et al. (2002). For the biological activity of heterocyclic compounds, see: Xu et al. (2006); Yu et al. (2009).

Experimental top

NaH (1.9 g, 0.08 mol) was dissolved in 30 ml DMF and cooled with an ice bath, then N,N'-di(p-toluenesulfonyl)ethane-1,2-diamine (7.4 g, 0.02 mol) in 10 ml DMF was added dropwise to the solution. After stirring 30 min, 1,3-dibromopropane in 5 ml DMF was added dropwise and the resulting suspension stirred overnight at room temperature. The residue was quenched by saturated NH₄Cl and extracted with ethyl acetate (3 × 200 ml). The combined organic layer was washed with saturated NaCl and dried over sodium sulfate. The solvent was removed and the residue was recrystallized from EtOH/DMF (5:1 v/v) to give the title compound (6.7 g, 82%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetonitrile at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with 40% probability displacement ellipsoids.

1,4-Ditosyl-1,4-diazepane top

Crystal data top

C₁₉H₂₄N₂O₄S₂	F(000) = 864
M_r = 408.52	D_x = 1.353 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7269 reflections
a = 6.3407 (13) Å	θ = 1.7–27.5°
b = 10.367 (2) Å	µ = 0.29 mm⁻¹
c = 30.516 (6) Å	T = 173 K
V = 2005.9 (7) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Rigaku Mercury CCD/AFC diffractometer	3531 independent reflections
Radiation source: Sealed Tube	3430 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −7→7
T_min = 0.944, T_max = 0.971	k = −8→12
11747 measured reflections	l = −36→35

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.035P)² + 0.4874P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3531 reflections	Δρ_max = 0.13 e Å⁻³
265 parameters	Δρ_min = −0.20 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 1442 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (7)

Crystal data top

C₁₉H₂₄N₂O₄S₂	V = 2005.9 (7) Å³
M_r = 408.52	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.3407 (13) Å	µ = 0.29 mm⁻¹
b = 10.367 (2) Å	T = 173 K
c = 30.516 (6) Å	0.20 × 0.20 × 0.10 mm

Data collection top

Rigaku Mercury CCD/AFC diffractometer	3531 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3430 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.971	R_int = 0.035
11747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.083	Δρ_max = 0.13 e Å⁻³
S = 1.07	Δρ_min = −0.20 e Å⁻³
3531 reflections	Absolute structure: Flack (1983), 1442 Friedel pairs
265 parameters	Absolute structure parameter: −0.03 (7)
6 restraints

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	Occ. (<1)
S1	0.84854 (9)	−0.00702 (6)	0.40081 (2)	0.04437 (16)
S2	0.83732 (9)	0.12928 (5)	0.22154 (2)	0.03921 (15)
O1	0.7421 (3)	0.08375 (18)	0.42783 (6)	0.0594 (5)
O2	1.0685 (3)	0.0089 (2)	0.39251 (7)	0.0716 (6)
O3	0.7251 (3)	0.24688 (15)	0.21378 (6)	0.0501 (4)
O4	1.0600 (2)	0.13432 (18)	0.22902 (6)	0.0532 (5)
N1	0.7323 (3)	−0.0080 (2)	0.35377 (6)	0.0439 (5)
N2	0.7313 (3)	0.06018 (17)	0.26359 (6)	0.0388 (5)
C1	0.6335 (4)	−0.1951 (3)	0.44536 (8)	0.0511 (6)
H1	0.5214	−0.1374	0.4464	0.061*
C2	0.6164 (5)	−0.3155 (3)	0.46458 (8)	0.0603 (8)
H2	0.4911	−0.3386	0.4783	0.072*
C3	0.7831 (6)	−0.4029 (3)	0.46375 (8)	0.0618 (8)
C4	0.9649 (5)	−0.3682 (3)	0.44218 (9)	0.0589 (7)
H4	1.0765	−0.4263	0.4408	0.071*
C5	0.9853 (4)	−0.2489 (3)	0.42246 (8)	0.0495 (6)
H5	1.1091	−0.2274	0.4079	0.059*
C6	0.8205 (4)	−0.1615 (2)	0.42453 (7)	0.0419 (5)
C8A	0.8715 (15)	−0.0801 (9)	0.3232 (2)	0.044 (2)	0.466 (13)
H8A1	0.8801	−0.1695	0.3323	0.053*	0.466 (13)
H8A2	1.0125	−0.0438	0.3241	0.053*	0.466 (13)
C9A	0.7867 (18)	−0.0729 (7)	0.2768 (3)	0.040 (2)	0.466 (13)
H9A1	0.8920	−0.1065	0.2568	0.048*	0.466 (13)
H9A2	0.6624	−0.1270	0.2745	0.048*	0.466 (13)
C8B	0.7774 (14)	−0.1092 (6)	0.31983 (19)	0.0377 (15)	0.534 (13)
H8B1	0.6480	−0.1544	0.3126	0.045*	0.534 (13)
H8B2	0.8765	−0.1714	0.3316	0.045*	0.534 (13)
C9B	0.8687 (11)	−0.0489 (7)	0.2785 (3)	0.0353 (17)	0.534 (13)
H9B1	1.0098	−0.0173	0.2844	0.042*	0.534 (13)
H9B2	0.8778	−0.1135	0.2556	0.042*	0.534 (13)
C10	0.5022 (4)	0.0686 (3)	0.26975 (8)	0.0517 (7)
H10A	0.4390	−0.0144	0.2633	0.062*
H10B	0.4447	0.1312	0.2494	0.062*
C11	0.4459 (4)	0.1078 (3)	0.31613 (9)	0.0518 (7)
H11A	0.5150	0.1891	0.3226	0.062*
H11B	0.2950	0.1226	0.3175	0.062*
C12	0.5040 (4)	0.0126 (3)	0.35127 (8)	0.0536 (7)
H12A	0.4535	0.0438	0.3793	0.064*
H12B	0.4350	−0.0691	0.3453	0.064*
C13	0.7984 (4)	0.0278 (2)	0.17594 (7)	0.0394 (5)
C14	0.9546 (4)	−0.0588 (2)	0.16374 (8)	0.0449 (6)
H14	1.0803	−0.0630	0.1794	0.054*
C15	0.9215 (4)	−0.1392 (3)	0.12792 (8)	0.0515 (6)
H15	1.0266	−0.1968	0.1196	0.062*
C16	0.7342 (5)	−0.1350 (3)	0.10436 (9)	0.0521 (6)
C17	0.5795 (4)	−0.0506 (3)	0.11791 (9)	0.0543 (7)
H17	0.4521	−0.0486	0.1028	0.065*
C18	0.6080 (4)	0.0313 (2)	0.15328 (8)	0.0469 (6)
H18	0.5015	0.0877	0.1618	0.056*
C19	0.7052 (6)	−0.2180 (3)	0.06426 (9)	0.0691 (9)
H19A	0.5637	−0.2509	0.0636	0.104*
H19B	0.8030	−0.2887	0.0652	0.104*
H19C	0.7305	−0.1673	0.0385	0.104*
C7	0.7658 (6)	−0.5318 (3)	0.48659 (10)	0.0877 (12)
H7A	0.7705	−0.5997	0.4652	0.131*
H7B	0.6349	−0.5359	0.5023	0.131*
H7C	0.8810	−0.5415	0.5067	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0326 (3)	0.0467 (3)	0.0537 (3)	−0.0031 (3)	0.0021 (3)	0.0001 (3)
S2	0.0305 (3)	0.0333 (3)	0.0538 (3)	−0.0003 (2)	−0.0042 (3)	0.0032 (3)
O1	0.0676 (13)	0.0522 (11)	0.0584 (11)	0.0016 (9)	−0.0065 (9)	−0.0171 (9)
O2	0.0299 (9)	0.0798 (14)	0.1052 (15)	−0.0070 (10)	0.0024 (10)	0.0327 (13)
O3	0.0498 (10)	0.0296 (8)	0.0710 (12)	0.0033 (7)	−0.0041 (9)	0.0093 (8)
O4	0.0271 (8)	0.0608 (11)	0.0717 (12)	−0.0036 (8)	−0.0061 (8)	−0.0080 (10)
N1	0.0411 (11)	0.0450 (11)	0.0457 (10)	0.0089 (9)	0.0087 (9)	−0.0023 (10)
N2	0.0373 (11)	0.0326 (10)	0.0464 (11)	0.0048 (8)	−0.0031 (9)	0.0025 (9)
C1	0.0479 (15)	0.0597 (16)	0.0458 (13)	−0.0042 (13)	0.0092 (12)	−0.0037 (12)
C2	0.073 (2)	0.0680 (18)	0.0401 (14)	−0.0238 (16)	0.0104 (14)	−0.0042 (13)
C3	0.094 (2)	0.0522 (16)	0.0395 (14)	−0.0121 (16)	−0.0093 (15)	−0.0031 (12)
C4	0.077 (2)	0.0505 (15)	0.0497 (15)	0.0081 (16)	−0.0049 (14)	−0.0054 (13)
C5	0.0482 (15)	0.0590 (16)	0.0413 (14)	0.0046 (13)	0.0025 (12)	−0.0031 (12)
C6	0.0394 (13)	0.0492 (14)	0.0370 (12)	−0.0026 (11)	0.0018 (11)	−0.0036 (10)
C8A	0.035 (4)	0.050 (4)	0.048 (4)	0.011 (4)	0.005 (3)	0.006 (3)
C9A	0.046 (5)	0.031 (3)	0.043 (4)	−0.001 (3)	−0.004 (4)	0.001 (3)
C8B	0.036 (4)	0.041 (3)	0.036 (3)	0.002 (3)	0.003 (3)	−0.005 (2)
C9B	0.035 (4)	0.030 (3)	0.041 (3)	0.006 (2)	−0.001 (3)	0.001 (3)
C10	0.0334 (13)	0.0642 (17)	0.0576 (16)	−0.0106 (12)	−0.0099 (11)	0.0107 (14)
C11	0.0268 (11)	0.0530 (16)	0.0758 (18)	0.0059 (11)	−0.0004 (12)	−0.0106 (13)
C12	0.0353 (13)	0.0765 (19)	0.0491 (14)	−0.0133 (13)	0.0033 (11)	−0.0035 (15)
C13	0.0356 (12)	0.0383 (12)	0.0442 (12)	−0.0016 (10)	−0.0024 (10)	0.0101 (10)
C14	0.0402 (13)	0.0438 (13)	0.0506 (14)	0.0029 (11)	−0.0007 (12)	0.0061 (12)
C15	0.0561 (16)	0.0442 (14)	0.0543 (15)	0.0045 (13)	0.0055 (13)	0.0047 (13)
C16	0.0640 (17)	0.0446 (13)	0.0477 (14)	−0.0054 (13)	−0.0038 (13)	0.0051 (13)
C17	0.0542 (16)	0.0577 (16)	0.0511 (14)	−0.0062 (13)	−0.0158 (13)	0.0090 (13)
C18	0.0413 (14)	0.0464 (14)	0.0529 (14)	0.0032 (11)	−0.0066 (11)	0.0019 (11)
C19	0.092 (2)	0.0543 (17)	0.0613 (18)	−0.0067 (17)	−0.0096 (17)	−0.0056 (14)
C7	0.140 (4)	0.063 (2)	0.0591 (18)	−0.028 (2)	−0.021 (2)	0.0131 (15)

Geometric parameters (Å, º) top

S1—O1	1.4216 (19)	C8B—C9B	1.522 (7)
S1—O2	1.4273 (18)	C8B—H8B1	0.9700
S1—N1	1.614 (2)	C8B—H8B2	0.9700
S1—C6	1.766 (2)	C9B—H9B1	0.9700
S2—O4	1.4313 (17)	C9B—H9B2	0.9700
S2—O3	1.4313 (16)	C10—C11	1.515 (4)
S2—N2	1.616 (2)	C10—H10A	0.9700
S2—C13	1.762 (2)	C10—H10B	0.9700
N1—C12	1.465 (3)	C11—C12	1.504 (4)
N1—C8A	1.486 (6)	C11—H11A	0.9700
N1—C8B	1.502 (5)	C11—H11B	0.9700
N2—C10	1.467 (3)	C12—H12A	0.9700
N2—C9A	1.480 (7)	C12—H12B	0.9700
N2—C9B	1.499 (6)	C13—C14	1.388 (3)
C1—C2	1.384 (4)	C13—C18	1.392 (3)
C1—C6	1.389 (4)	C14—C15	1.391 (4)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.392 (4)	C15—C16	1.389 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.375 (4)	C16—C17	1.378 (4)
C3—C7	1.511 (4)	C16—C19	1.507 (4)
C4—C5	1.381 (4)	C17—C18	1.385 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.385 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C8A—C9A	1.516 (8)	C19—H19B	0.9600
C8A—H8A1	0.9700	C19—H19C	0.9600
C8A—H8A2	0.9700	C7—H7A	0.9600
C9A—H9A1	0.9700	C7—H7B	0.9600
C9A—H9A2	0.9700	C7—H7C	0.9600

O1—S1—O2	119.36 (13)	C9B—C8B—H8B2	109.5
O1—S1—N1	107.66 (11)	H8B1—C8B—H8B2	108.0
O2—S1—N1	106.80 (12)	N2—C9B—C8B	109.9 (5)
O1—S1—C6	108.33 (12)	N2—C9B—H9B1	109.7
O2—S1—C6	106.02 (12)	C8B—C9B—H9B1	109.7
N1—S1—C6	108.25 (11)	N2—C9B—H9B2	109.7
O4—S2—O3	119.05 (11)	C8B—C9B—H9B2	109.7
O4—S2—N2	107.45 (11)	H9B1—C9B—H9B2	108.2
O3—S2—N2	107.59 (10)	N2—C10—C11	111.7 (2)
O4—S2—C13	106.62 (11)	N2—C10—H10A	109.3
O3—S2—C13	107.95 (11)	C11—C10—H10A	109.3
N2—S2—C13	107.71 (10)	N2—C10—H10B	109.3
C12—N1—C8A	128.8 (4)	C11—C10—H10B	109.3
C12—N1—C8B	104.7 (4)	H10A—C10—H10B	107.9
C12—N1—S1	119.77 (16)	C12—C11—C10	115.6 (2)
C8A—N1—S1	106.9 (3)	C12—C11—H11A	108.4
C8B—N1—S1	122.1 (3)	C10—C11—H11A	108.4
C10—N2—C9A	104.8 (5)	C12—C11—H11B	108.4
C10—N2—C9B	125.6 (3)	C10—C11—H11B	108.4
C10—N2—S2	119.14 (16)	H11A—C11—H11B	107.4
C9A—N2—S2	122.1 (5)	N1—C12—C11	112.0 (2)
C9B—N2—S2	109.5 (3)	N1—C12—H12A	109.2
C2—C1—C6	119.2 (3)	C11—C12—H12A	109.2
C2—C1—H1	120.4	N1—C12—H12B	109.2
C6—C1—H1	120.4	C11—C12—H12B	109.2
C1—C2—C3	121.3 (3)	H12A—C12—H12B	107.9
C1—C2—H2	119.3	C14—C13—C18	120.2 (2)
C3—C2—H2	119.3	C14—C13—S2	119.87 (18)
C4—C3—C2	118.4 (3)	C18—C13—S2	119.90 (19)
C4—C3—C7	120.9 (3)	C13—C14—C15	119.4 (2)
C2—C3—C7	120.8 (3)	C13—C14—H14	120.3
C3—C4—C5	121.4 (3)	C15—C14—H14	120.3
C3—C4—H4	119.3	C16—C15—C14	121.1 (3)
C5—C4—H4	119.3	C16—C15—H15	119.4
C4—C5—C6	119.7 (3)	C14—C15—H15	119.4
C4—C5—H5	120.1	C17—C16—C15	118.3 (3)
C6—C5—H5	120.1	C17—C16—C19	121.3 (3)
C5—C6—C1	120.0 (2)	C15—C16—C19	120.5 (3)
C5—C6—S1	119.9 (2)	C16—C17—C18	122.0 (3)
C1—C6—S1	120.1 (2)	C16—C17—H17	119.0
N1—C8A—C9A	110.6 (7)	C18—C17—H17	119.0
N1—C8A—H8A1	109.5	C17—C18—C13	119.0 (2)
C9A—C8A—H8A1	109.5	C17—C18—H18	120.5
N1—C8A—H8A2	109.5	C13—C18—H18	120.5
C9A—C8A—H8A2	109.5	C16—C19—H19A	109.5
H8A1—C8A—H8A2	108.1	C16—C19—H19B	109.5
N2—C9A—C8A	112.6 (6)	H19A—C19—H19B	109.5
N2—C9A—H9A1	109.1	C16—C19—H19C	109.5
C8A—C9A—H9A1	109.1	H19A—C19—H19C	109.5
N2—C9A—H9A2	109.1	H19B—C19—H19C	109.5
C8A—C9A—H9A2	109.1	C3—C7—H7A	109.5
H9A1—C9A—H9A2	107.8	C3—C7—H7B	109.5
N1—C8B—C9B	110.9 (6)	H7A—C7—H7B	109.5
N1—C8B—H8B1	109.5	C3—C7—H7C	109.5
C9B—C8B—H8B1	109.5	H7A—C7—H7C	109.5
N1—C8B—H8B2	109.5	H7B—C7—H7C	109.5

O1—S1—N1—C12	−34.0 (3)	S1—N1—C8A—C9A	−173.6 (8)
O2—S1—N1—C12	−163.3 (2)	C10—N2—C9A—C8A	−98.8 (10)
C6—S1—N1—C12	82.9 (2)	C9B—N2—C9A—C8A	60.8 (13)
O1—S1—N1—C8A	167.7 (5)	S2—N2—C9A—C8A	121.8 (9)
O2—S1—N1—C8A	38.4 (5)	N1—C8A—C9A—N2	48.4 (15)
C6—S1—N1—C8A	−75.4 (5)	C12—N1—C8B—C9B	101.7 (7)
O1—S1—N1—C8B	−168.7 (4)	C8A—N1—C8B—C9B	−57.8 (9)
O2—S1—N1—C8B	62.0 (4)	S1—N1—C8B—C9B	−118.0 (6)
C6—S1—N1—C8B	−51.8 (4)	C10—N2—C9B—C8B	−30.9 (10)
O4—S2—N2—C10	165.87 (18)	C9A—N2—C9B—C8B	−55.4 (14)
O3—S2—N2—C10	36.5 (2)	S2—N2—C9B—C8B	176.4 (6)
C13—S2—N2—C10	−79.6 (2)	N1—C8B—C9B—N2	−51.2 (11)
O4—S2—N2—C9A	−60.1 (4)	C9A—N2—C10—C11	87.3 (4)
O3—S2—N2—C9A	170.6 (4)	C9B—N2—C10—C11	77.9 (6)
C13—S2—N2—C9A	54.4 (4)	S2—N2—C10—C11	−131.8 (2)
O4—S2—N2—C9B	−39.4 (4)	N2—C10—C11—C12	−65.3 (3)
O3—S2—N2—C9B	−168.8 (4)	C8A—N1—C12—C11	−73.4 (6)
C13—S2—N2—C9B	75.1 (4)	C8B—N1—C12—C11	−84.8 (3)
C6—C1—C2—C3	0.5 (4)	S1—N1—C12—C11	133.74 (19)
C1—C2—C3—C4	−1.8 (4)	C10—C11—C12—N1	62.6 (3)
C1—C2—C3—C7	177.3 (3)	O4—S2—C13—C14	20.1 (2)
C2—C3—C4—C5	1.3 (4)	O3—S2—C13—C14	149.10 (19)
C7—C3—C4—C5	−177.7 (3)	N2—S2—C13—C14	−95.0 (2)
C3—C4—C5—C6	0.4 (4)	O4—S2—C13—C18	−162.33 (19)
C4—C5—C6—C1	−1.7 (4)	O3—S2—C13—C18	−33.3 (2)
C4—C5—C6—S1	178.10 (19)	N2—S2—C13—C18	82.6 (2)
C2—C1—C6—C5	1.2 (4)	C18—C13—C14—C15	1.9 (4)
C2—C1—C6—S1	−178.58 (19)	S2—C13—C14—C15	179.45 (18)
O1—S1—C6—C5	−143.5 (2)	C13—C14—C15—C16	−0.5 (4)
O2—S1—C6—C5	−14.2 (2)	C14—C15—C16—C17	−1.3 (4)
N1—S1—C6—C5	100.1 (2)	C14—C15—C16—C19	176.9 (2)
O1—S1—C6—C1	36.3 (2)	C15—C16—C17—C18	1.6 (4)
O2—S1—C6—C1	165.6 (2)	C19—C16—C17—C18	−176.5 (3)
N1—S1—C6—C1	−80.1 (2)	C16—C17—C18—C13	−0.3 (4)
C12—N1—C8A—C9A	30.8 (12)	C14—C13—C18—C17	−1.5 (4)
C8B—N1—C8A—C9A	56.6 (10)	S2—C13—C18—C17	−179.09 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3	0.97	2.40	2.886 (3)	110
C12—H12A···O1	0.97	2.39	2.878 (3)	111
C10—H10B···O4ⁱ	0.97	2.52	3.142 (3)	122
C12—H12A···O2ⁱ	0.97	2.50	3.035 (3)	115

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₄S₂
M_r	408.52
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	6.3407 (13), 10.367 (2), 30.516 (6)
V (Å³)	2005.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku Mercury CCD/AFC diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.944, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	11747, 3531, 3430
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.083, 1.07
No. of reflections	3531
No. of parameters	265
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.20
Absolute structure	Flack (1983), 1442 Friedel pairs
Absolute structure parameter	−0.03 (7)

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3	0.97	2.40	2.886 (3)	110
C12—H12A···O1	0.97	2.39	2.878 (3)	111
C10—H10B···O4ⁱ	0.97	2.52	3.142 (3)	122
C12—H12A···O2ⁱ	0.97	2.50	3.035 (3)	115

Symmetry code: (i) x−1, y, z.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Romba, J., Steinhauser, S. & Hegetschweiler, K. (2002). Z. Kristallogr. New Cryst. Struct. 217, 133–134. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, L. Z., Huang, Y. W., Yu, G. P., Si, G. D. & Zhu, Q. (2006). Struct. Chem. 17, 235–239. Web of Science CSD CrossRef CAS Google Scholar
Yu, G. P., Xu, L. Z., Yi, X., Bi, W. Z., Zhu, Q. & Zhai, Z. W. (2009). J. Agric. Food Chem. 57, 4854–4860. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 6| June 2012| Page o1716

doi:10.1107/S1600536812020958

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