trans-4,5-Dihydr­oxy-1,3-bis­(4-methoxy­phen­yl)imidazolidine-2-thione

Zhang, Z.; Wang, J.; Zhang, G.

doi:10.1107/S1600536809042779

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2827

https://doi.org/10.1107/S1600536809042779

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trans-4,5-Dihydroxy-1,3-bis(4-methoxyphenyl)imidazolidine-2-thione

Zhenfeng Zhang,^a ^* Jiange Wang ^b and Guisheng Zhang ^a

^aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, People's Republic of China, and ^bCollege of Chemistry, Luoyang Normal University, Xinxiang 453007, People's Republic of China
^*Correspondence e-mail: zzf5188@sohu.com

(Received 10 September 2009; accepted 17 October 2009; online 23 October 2009)

In the title compound, C₁₇H₁₈N₂O₄S, where one of the N-4-methoxyphenyl fragments is disordered over two sets of sites, the five-membered ring exhibits a nearly half-chair conformation and the two hydroxyl groups lie on opposite sides of the five-membered ring. In the crystal, the molecules are linked into sheets parallel to (100) via O—H⋯O and O—H⋯S hydrogen bonds.

Related literature

For the bioactivity of imidazolidine-2-one derivatives, see: Lam et al. (1994 ); Lenzen & Ahmad (2001 ); Perronnet & Teche (1973 ). For related structures, see: Zhang et al. (2007 , 2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₄S
M_r = 346.39
Monoclinic, P 2₁ /c
a = 13.9807 (12) Å
b = 12.1789 (11) Å
c = 10.0958 (9) Å
β = 93.815 (1)°
V = 1715.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 294 K
0.49 × 0.35 × 0.34 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.904, T_max = 0.931
12720 measured reflections
3179 independent reflections
2654 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.03
3179 reflections
244 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.99	2.7971 (19)	169
O1—H1⋯S1ⁱⁱ	0.82	2.40	3.1799 (14)	158
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 datablock I. DOI: https://doi.org/10.1107/S1600536809042779/fl2268sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042779/fl2268Isup2.hkl

checkCIF report

Comment top

Imidazolidine-2-one derivates often exhibit powerful bioactivitiy, as herbicides (Perronnet & Teche,1973), antidiabetics (Lenzen & Ahmad, 2001) and anti-HIV agents (Lam et al., 1994). Enders and his workers have earlier reported the synthesis and use of 4,5-dihydroxyimidazolidine-2-thiones. However, to our knowledge, there are few N,N'-diarylsubstituted 4,5-dihydroxyimidazolidine-2-thiones reported so far. As a continuation of our structural studies of such compounds (Zhang et al., 2009), we report here the molecular and supramolecular structures of (I) (Fig. 1).

In (I), the N2-containing (4-methoxyphenyl)imino group is disordered over two sites with refined occupancies of 0.747 (2) and 0.253 (2) (Fig. 1). The five-membered ring adopts a nearly half-chair conformation; the total puckering amplitudes Q₂ (Cremer & Pople, 1975) are 0.247 (5) and 0.187 (11) Å, and the ring puckering parameters φ₂ are 302.1 (9) and 333 (5)°, respectively, for the atom sequences, N1—C1—N2—C3—C2 and N1—C1—N2'—C3—C2. For an idealized half-chair, the ring puckering angle is φ₂ = (36k + 18) ° (where k = zero or an integer). Therefore, the conformation for the five-membered ring in (I) is markedly different from that found in our previously reported compound (Zhang et al., 2007), where the five-membered ring shows a perfect envelope conformation. The difference in conformation is mainly attributed to van der Waals repulsions between the five-membered ring and its N1 and N2 phenyl substituents. Due to the existence of the van der Waals repulsions, the aryl groups exhibit nearly perpendicular orientations to the five-membered ring with the dihedral angle between the planes C4–C9 and C1/N1/C2 being 73.1 (2) °. Meanwhile, the dihedral angle between the planes C10–C15 and C1/N2/C3 is 89.7 (9) °. In addition, the C7 and C13 methoxy groups adopt closely coplanar orientations, respectively to their attached aryl rings, as shown by the torsion angles of C6—C7—O3—C16 [5.4 (4) °] and C14—C13—O4—C17 [6.4 (13) °]. Interestingly, the molecule (I) adopts a trans configuration (Fig. 1); the two hydroxyl groups lie on opposite sides of the five-membered ring. In view of the same trans configuration in 4,5-dihydroxyimidazolidine-2-thiones (Zhang et al., 2007; Zhang et al., 2009), we can draw a general conclusion that this trans-configuration is probably ubiquitous in 4,5-dihydroxyimidazolidine- 2-thiones.

The heterocyclic geometries of (I) also present some unexpected features. The C1—N1[1.366 (2) Å] and C1—N2 [1.352 (6) Å] bonds are significantly longer than the corresponding bonds in 4,5-dihydroxyimidazolidine-2-thione [1.335 (2) and 1.336 (2) Å; Zhang et al., 2007]. Conversely, the C1-S1[1.669 (2) Å] and C2—C3 [1.523 (2) Å] bonds are shorter than the corresponding bonds in 4,5-dihydroxyimidazolidine-2-thione [1.684 (2) and 1.537 (2) Å, respectively].

In analyzing the supramolecular structure of (I), for the sake of simplicity, we shall omit any consideration of the intermolecular C—H···O interactions involving a C—H bond from an aromatic ring, which is far too long to be significant. Thus, molecules of (I) are linked into sheets by only two independent O—H···S and O—H···O hydrogen bonds (Table 1), the formation of which is readily analyzed in terms of two one-dimensional substructures. In the first substructure, hydroxyl atom O1 in the molecule at (x,y,z) acts as a hydrogen-bond donor to thiocarbonyl atom S1 in the molecule at (-x, y - 1/2,-z + 3/2), so forming a C₂²(6) (Bernstein et al.,1995) chain along [010] and generated by 2₁ screw axis along (0,y,3/4) (Fig. 2). Similarly in the second substructure, hydroxyl atom O2 in the molecule at (x,y,z) acts as a hydrogen-bond donor to hydroxyl atom O1 in the molecule at (x,-y + 3/2,z + 1/2), so forming a C(5) (Bernstein et al., 1995) chain parallel to [001], this time generated by a 2₁ screw along (1/8,3/4,z) (Fig. 2). The combination of the two chain motifs is sufficient to link all the molecules into a sheet parallel to (100). Two such sheets pass through each unit cell; in each sheet, there are both enantiomers of (I); there are no direction-specific interactions between adjacent sheets, in particular C—H···π hydrogen bonds and π-π stacking interactions are absent.

Related literature top

For the bioactivity of imidazolidine-2-one derivatives, see: Lam et al. (1994); Lenzen & Ahmad (2001); Perronnet & Teche (1973). For related structures, see: Zhang et al. (2007, 2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Into a three-necked round-bottomed flask equipped with a stirrer were introduced 1,3-bis(4-methoxyphenyl)thiourea(0.1 mol), glyoxal (40%, 18 g) and ethanol (95%, 30 ml). The mixture was then refluxed with stirring for ca 30 min and thereafter the solvent was removed; the residue was washed with cold ethanol and the resulting solid product was recrystallized from hot ethanol to give crystals of (I).

¹H NMR(DMSO, 400 MHz) of (I): δ 7.36–6.95 (m, 8H), δ 7.1 (d, J = 8.0 Hz, 2H), δ 5.08 (d, J = 8.4 Hz, 2H), δ 3.76 (s, 6H).

Structure description top

For the bioactivity of imidazolidine-2-one derivatives, see: Lam et al. (1994); Lenzen & Ahmad (2001); Perronnet & Teche (1973). For related structures, see: Zhang et al. (2007, 2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a (100) sheet. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Intermolecular interactions are represented by dashed lines. Selected atoms are labelled. [Symmetry codes: (i) -x,y - 1/2,-z + 3/2; (ii) x + 1,-y + 3/2,z + 1/2; (iii) -x,y + 1/2,-z + 3/2; (iv) x,-y + 3/2,z + 1/2].

trans-4,5-Dihydroxy-1,3-bis(4-methoxyphenyl)imidazolidine-2-thione top

Crystal data top

C₁₇H₁₈N₂O₄S	F(000) = 728
M_r = 346.39	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9807 (12) Å	Cell parameters from 4930 reflections
b = 12.1789 (11) Å	θ = 2.6–26.9°
c = 10.0958 (9) Å	µ = 0.21 mm⁻¹
β = 93.815 (1)°	T = 294 K
V = 1715.2 (3) Å³	Block, colorless
Z = 4	0.49 × 0.35 × 0.34 mm

Data collection top

Bruker SMART CCD diffractometer	3179 independent reflections
Radiation source: fine-focus sealed tube	2654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
phi and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
T_min = 0.904, T_max = 0.931	k = −14→14
12720 measured reflections	l = −12→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0522P)² + 0.751P] where P = (F_o² + 2F_c²)/3
3179 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.41 e Å⁻³
10 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₄S	V = 1715.2 (3) Å³
M_r = 346.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.9807 (12) Å	µ = 0.21 mm⁻¹
b = 12.1789 (11) Å	T = 294 K
c = 10.0958 (9) Å	0.49 × 0.35 × 0.34 mm
β = 93.815 (1)°

Data collection top

Bruker SMART CCD diffractometer	3179 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2654 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.931	R_int = 0.019
12720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	10 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
3179 reflections	Δρ_min = −0.60 e Å⁻³
244 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	Occ. (<1)
N2	0.1894 (5)	0.8182 (5)	0.8627 (11)	0.0376 (14)	0.746 (2)
C10	0.2878 (3)	0.8426 (4)	0.8958 (3)	0.0387 (8)	0.746 (2)
C11	0.3522 (2)	0.8265 (2)	0.7987 (3)	0.0538 (7)	0.746 (2)
H11	0.3295	0.8116	0.7119	0.065*	0.746 (2)
C12	0.4492 (2)	0.8325 (3)	0.8299 (3)	0.0644 (8)	0.746 (2)
H12	0.4920	0.8229	0.7640	0.077*	0.746 (2)
C13	0.4833 (2)	0.8528 (2)	0.9598 (3)	0.0532 (7)	0.746 (2)
C14	0.4205 (2)	0.8754 (3)	1.0555 (3)	0.0542 (8)	0.746 (2)
H14	0.4432	0.8936	1.1413	0.065*	0.746 (2)
C15	0.3222 (2)	0.8705 (2)	1.0222 (3)	0.0480 (7)	0.746 (2)
H15	0.2793	0.8863	1.0862	0.058*	0.746 (2)
C17	0.6212 (9)	0.861 (2)	1.1138 (17)	0.0922 (15)	0.746 (2)
H17A	0.5976	0.9264	1.1523	0.138*	0.746 (2)
H17B	0.6898	0.8640	1.1139	0.138*	0.746 (2)
H17C	0.6031	0.7982	1.1648	0.138*	0.746 (2)
O4	0.58130 (14)	0.8499 (2)	0.9808 (3)	0.0785 (7)	0.746 (2)
N2'	0.1897 (16)	0.8218 (15)	0.883 (4)	0.0376 (14)	0.254 (2)
C10'	0.2843 (11)	0.8530 (16)	0.9341 (14)	0.0387 (8)	0.254 (2)
C11'	0.3624 (6)	0.8085 (8)	0.8804 (9)	0.0538 (7)	0.254 (2)
H11'	0.3560	0.7707	0.8003	0.065*	0.254 (2)
C12'	0.4518 (7)	0.8206 (10)	0.9478 (12)	0.0644 (8)	0.254 (2)
H12'	0.5064	0.7924	0.9123	0.077*	0.254 (2)
C13'	0.4586 (7)	0.8747 (9)	1.0675 (13)	0.0532 (7)	0.254 (2)
C14'	0.3778 (6)	0.9179 (8)	1.1206 (9)	0.0542 (8)	0.254 (2)
H14'	0.3837	0.9566	1.2001	0.065*	0.254 (2)
C15'	0.2897 (7)	0.9037 (8)	1.0563 (9)	0.0480 (7)	0.254 (2)
H15'	0.2345	0.9277	1.0941	0.058*	0.254 (2)
C17'	0.629 (3)	0.854 (7)	1.100 (6)	0.0922 (15)	0.254 (2)
H17D	0.6417	0.7791	1.1256	0.138*	0.254 (2)
H17E	0.6805	0.8998	1.1347	0.138*	0.254 (2)
H17F	0.6243	0.8588	1.0044	0.138*	0.254 (2)
O4'	0.5427 (4)	0.8885 (6)	1.1491 (8)	0.0785 (7)	0.254 (2)
S1	0.12664 (3)	1.02415 (4)	0.81566 (5)	0.04968 (17)
O1	0.06318 (10)	0.66792 (11)	0.68364 (12)	0.0507 (4)
H1	0.0227	0.6199	0.6696	0.076*
O2	0.15350 (10)	0.68187 (11)	1.02357 (12)	0.0498 (3)
H2	0.1261	0.7311	1.0616	0.075*
O3	−0.33055 (13)	0.9381 (2)	0.6034 (2)	0.1059 (6)
N1	0.03525 (10)	0.82649 (12)	0.81002 (15)	0.0404 (3)
C1	0.11643 (11)	0.88826 (14)	0.83077 (16)	0.0368 (4)
C2	0.05733 (13)	0.70931 (15)	0.81329 (17)	0.0409 (4)
H2A	0.0101	0.6685	0.8611	0.049*
C3	0.15534 (13)	0.70725 (14)	0.88879 (17)	0.0405 (4)
H3	0.1963	0.6541	0.8466	0.049*
C4	−0.05667 (12)	0.86336 (15)	0.75615 (17)	0.0402 (4)
C5	−0.06968 (13)	0.90132 (16)	0.62842 (18)	0.0446 (4)
H5	−0.0168	0.9098	0.5782	0.054*
C6	−0.16006 (14)	0.92724 (17)	0.5726 (2)	0.0509 (5)
H6	−0.1680	0.9526	0.4857	0.061*
C7	−0.23823 (14)	0.9148 (2)	0.6480 (2)	0.0602 (6)
C8	−0.22540 (15)	0.8775 (2)	0.7771 (2)	0.0737 (7)
H8	−0.2782	0.8698	0.8277	0.088*
C9	−0.13567 (14)	0.8517 (2)	0.8319 (2)	0.0601 (6)
H9	−0.1277	0.8267	0.9190	0.072*
C16	−0.34805 (19)	0.9682 (3)	0.4689 (3)	0.1059 (6)
H16A	−0.3167	1.0367	0.4531	0.159*
H16B	−0.4158	0.9761	0.4489	0.159*
H16C	−0.3235	0.9124	0.4132	0.159*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0346 (8)	0.0367 (9)	0.041 (4)	−0.0025 (6)	−0.0037 (13)	0.0023 (13)
C10	0.0363 (11)	0.0352 (15)	0.044 (3)	0.0000 (9)	−0.0051 (17)	−0.0031 (18)
C11	0.0475 (14)	0.0643 (16)	0.0496 (16)	−0.0027 (12)	0.0039 (14)	−0.0145 (15)
C12	0.0405 (14)	0.076 (2)	0.0784 (19)	−0.0006 (13)	0.0130 (14)	−0.0227 (17)
C13	0.0337 (15)	0.0461 (15)	0.0786 (19)	−0.0015 (11)	−0.0059 (14)	0.0030 (14)
C14	0.0476 (19)	0.0632 (18)	0.0502 (17)	−0.0093 (16)	−0.0092 (14)	0.0047 (13)
C15	0.0443 (17)	0.0579 (19)	0.0419 (16)	−0.0056 (13)	0.0029 (12)	−0.0013 (12)
C17	0.052 (3)	0.098 (4)	0.122 (5)	−0.017 (2)	−0.030 (2)	0.028 (3)
O4	0.0357 (10)	0.0820 (15)	0.1161 (19)	−0.0034 (10)	−0.0094 (11)	0.0010 (13)
N2'	0.0346 (8)	0.0367 (9)	0.041 (4)	−0.0025 (6)	−0.0037 (13)	0.0023 (13)
C10'	0.0363 (11)	0.0352 (15)	0.044 (3)	0.0000 (9)	−0.0051 (17)	−0.0031 (18)
C11'	0.0475 (14)	0.0643 (16)	0.0496 (16)	−0.0027 (12)	0.0039 (14)	−0.0145 (15)
C12'	0.0405 (14)	0.076 (2)	0.0784 (19)	−0.0006 (13)	0.0130 (14)	−0.0227 (17)
C13'	0.0337 (15)	0.0461 (15)	0.0786 (19)	−0.0015 (11)	−0.0059 (14)	0.0030 (14)
C14'	0.0476 (19)	0.0632 (18)	0.0502 (17)	−0.0093 (16)	−0.0092 (14)	0.0047 (13)
C15'	0.0443 (17)	0.0579 (19)	0.0419 (16)	−0.0056 (13)	0.0029 (12)	−0.0013 (12)
C17'	0.052 (3)	0.098 (4)	0.122 (5)	−0.017 (2)	−0.030 (2)	0.028 (3)
O4'	0.0357 (10)	0.0820 (15)	0.1161 (19)	−0.0034 (10)	−0.0094 (11)	0.0010 (13)
S1	0.0414 (3)	0.0359 (3)	0.0700 (4)	−0.00154 (19)	−0.0095 (2)	−0.0005 (2)
O1	0.0596 (9)	0.0473 (8)	0.0449 (7)	−0.0153 (6)	0.0015 (6)	−0.0073 (6)
O2	0.0591 (9)	0.0482 (8)	0.0417 (7)	0.0025 (6)	0.0011 (6)	0.0083 (6)
O3	0.0481 (8)	0.1623 (18)	0.1038 (13)	0.0091 (9)	−0.0214 (8)	0.0229 (12)
N1	0.0348 (8)	0.0394 (8)	0.0463 (8)	−0.0035 (6)	−0.0028 (6)	−0.0003 (6)
C1	0.0329 (9)	0.0419 (9)	0.0353 (8)	−0.0004 (7)	−0.0013 (7)	−0.0010 (7)
C2	0.0426 (10)	0.0399 (10)	0.0402 (9)	−0.0087 (8)	0.0037 (7)	0.0012 (7)
C3	0.0429 (10)	0.0372 (9)	0.0412 (9)	−0.0008 (7)	0.0026 (7)	0.0024 (7)
C4	0.0327 (9)	0.0442 (10)	0.0433 (10)	−0.0041 (7)	−0.0007 (7)	−0.0047 (8)
C5	0.0412 (10)	0.0480 (10)	0.0449 (10)	−0.0015 (8)	0.0044 (8)	−0.0018 (8)
C6	0.0511 (11)	0.0536 (12)	0.0467 (10)	0.0004 (9)	−0.0072 (9)	0.0009 (9)
C7	0.0379 (11)	0.0709 (14)	0.0702 (14)	−0.0008 (10)	−0.0092 (10)	−0.0009 (11)
C8	0.0370 (11)	0.117 (2)	0.0681 (15)	−0.0030 (12)	0.0095 (10)	0.0065 (14)
C9	0.0434 (11)	0.0916 (17)	0.0452 (11)	−0.0045 (11)	0.0029 (9)	0.0067 (11)
C16	0.0481 (8)	0.1623 (18)	0.1038 (13)	0.0091 (9)	−0.0214 (8)	0.0229 (12)

Geometric parameters (Å, º) top

N2—C1	1.352 (6)	C15'—H15'	0.9300
N2—C10	1.426 (6)	C17'—O4'	1.40 (2)
N2—C3	1.462 (6)	C17'—H17D	0.9600
C10—C15	1.376 (4)	C17'—H17E	0.9600
C10—C11	1.388 (5)	C17'—H17F	0.9600
C11—C12	1.374 (4)	S1—C1	1.669 (2)
C11—H11	0.9300	O1—C2	1.410 (2)
C12—C13	1.388 (5)	O1—H1	0.8200
C12—H12	0.9300	O2—C3	1.397 (2)
C13—O4	1.372 (3)	O2—H2	0.8200
C13—C14	1.376 (5)	O3—C7	1.368 (3)
C14—C15	1.394 (4)	O3—C16	1.413 (4)
C14—H14	0.9300	N1—C1	1.366 (2)
C15—H15	0.9300	N1—C4	1.434 (2)
C17—O4	1.426 (17)	N1—C2	1.460 (2)
C17—H17A	0.9600	C2—C3	1.523 (2)
C17—H17B	0.9600	C2—H2A	0.9800
C17—H17C	0.9600	C3—H3	0.9800
N2'—C1	1.382 (17)	C4—C5	1.371 (3)
N2'—C10'	1.438 (17)	C4—C9	1.392 (3)
N2'—C3	1.478 (17)	C5—C6	1.385 (3)
C10'—C11'	1.364 (14)	C5—H5	0.9300
C10'—C15'	1.377 (13)	C6—C7	1.381 (3)
C11'—C12'	1.391 (12)	C6—H6	0.9300
C11'—H11'	0.9300	C7—C8	1.381 (3)
C12'—C13'	1.374 (18)	C8—C9	1.373 (3)
C12'—H12'	0.9300	C8—H8	0.9300
C13'—C14'	1.385 (15)	C9—H9	0.9300
C13'—O4'	1.400 (12)	C16—H16A	0.9600
C14'—C15'	1.365 (12)	C16—H16B	0.9600
C14'—H14'	0.9300	C16—H16C	0.9600

C1—N2—C10	128.7 (5)	C3—O2—H2	109.5
C1—N2—C3	112.1 (5)	C7—O3—C16	118.0 (2)
C10—N2—C3	118.1 (4)	C1—N1—C4	126.88 (15)
C15—C10—C11	119.1 (4)	C1—N1—C2	111.25 (14)
C15—C10—N2	122.8 (6)	C4—N1—C2	119.84 (14)
C11—C10—N2	117.8 (5)	N2—C1—N1	107.1 (3)
C12—C11—C10	120.5 (3)	N2—C1—N2'	9 (2)
C12—C11—H11	119.7	N1—C1—N2'	108.9 (8)
C10—C11—H11	119.7	N2—C1—S1	125.4 (3)
C11—C12—C13	119.8 (3)	N1—C1—S1	127.39 (13)
C11—C12—H12	120.1	N2'—C1—S1	123.4 (7)
C13—C12—H12	120.1	O1—C2—N1	110.71 (14)
O4—C13—C14	125.1 (3)	O1—C2—C3	110.66 (15)
O4—C13—C12	114.7 (3)	N1—C2—C3	102.08 (13)
C14—C13—C12	120.2 (3)	O1—C2—H2A	111.0
C13—C14—C15	119.2 (3)	N1—C2—H2A	111.0
C13—C14—H14	120.4	C3—C2—H2A	111.0
C15—C14—H14	120.4	O2—C3—N2	114.0 (5)
C10—C15—C14	120.8 (3)	O2—C3—N2'	106.0 (16)
C10—C15—H15	119.6	N2—C3—N2'	8 (2)
C14—C15—H15	119.6	O2—C3—C2	114.63 (15)
C13—O4—C17	117.8 (5)	N2—C3—C2	100.8 (3)
C1—N2'—C10'	128.5 (15)	N2'—C3—C2	104.4 (7)
C1—N2'—C3	109.5 (12)	O2—C3—H3	109.0
C10'—N2'—C3	121.9 (14)	N2—C3—H3	109.0
C11'—C10'—C15'	122.4 (13)	N2'—C3—H3	113.9
C11'—C10'—N2'	119.6 (18)	C2—C3—H3	109.0
C15'—C10'—N2'	116 (2)	C5—C4—C9	119.39 (17)
C10'—C11'—C12'	118.8 (10)	C5—C4—N1	121.47 (16)
C10'—C11'—H11'	120.6	C9—C4—N1	118.93 (17)
C12'—C11'—H11'	120.6	C4—C5—C6	121.34 (18)
C13'—C12'—C11'	119.2 (9)	C4—C5—H5	119.3
C13'—C12'—H12'	120.4	C6—C5—H5	119.3
C11'—C12'—H12'	120.4	C7—C6—C5	118.96 (19)
C12'—C13'—C14'	120.8 (9)	C7—C6—H6	120.5
C12'—C13'—O4'	125.5 (10)	C5—C6—H6	120.5
C14'—C13'—O4'	113.6 (10)	O3—C7—C8	116.0 (2)
C15'—C14'—C13'	120.1 (9)	O3—C7—C6	124.0 (2)
C15'—C14'—H14'	120.0	C8—C7—C6	119.92 (19)
C13'—C14'—H14'	120.0	C9—C8—C7	120.9 (2)
C14'—C15'—C10'	118.5 (11)	C9—C8—H8	119.6
C14'—C15'—H15'	120.8	C7—C8—H8	119.6
C10'—C15'—H15'	120.8	C8—C9—C4	119.5 (2)
O4'—C17'—H17D	109.5	C8—C9—H9	120.2
O4'—C17'—H17E	109.5	C4—C9—H9	120.2
H17D—C17'—H17E	109.5	O3—C16—H16A	109.5
O4'—C17'—H17F	109.5	O3—C16—H16B	109.5
H17D—C17'—H17F	109.5	H16A—C16—H16B	109.5
H17E—C17'—H17F	109.5	O3—C16—H16C	109.5
C13'—O4'—C17'	118 (2)	H16A—C16—H16C	109.5
C2—O1—H1	109.5	H16B—C16—H16C	109.5

C1—N2—C10—C15	84.6 (12)	C10'—N2'—C1—N2	108 (10)
C3—N2—C10—C15	−82.6 (9)	C3—N2'—C1—N2	−76 (6)
C1—N2—C10—C11	−102.0 (11)	C10'—N2'—C1—N1	−172 (3)
C3—N2—C10—C11	90.9 (9)	C3—N2'—C1—N1	4 (3)
C15—C10—C11—C12	3.5 (7)	C10'—N2'—C1—S1	1 (5)
N2—C10—C11—C12	−170.2 (4)	C3—N2'—C1—S1	176.9 (12)
C10—C11—C12—C13	1.1 (5)	C1—N1—C2—O1	−97.38 (16)
C11—C12—C13—O4	176.0 (3)	C4—N1—C2—O1	67.5 (2)
C11—C12—C13—C14	−5.0 (5)	C1—N1—C2—C3	20.43 (18)
O4—C13—C14—C15	−176.9 (3)	C4—N1—C2—C3	−174.67 (14)
C12—C13—C14—C15	4.1 (5)	C1—N2—C3—O2	−100.6 (7)
C11—C10—C15—C14	−4.4 (7)	C10—N2—C3—O2	68.6 (9)
N2—C10—C15—C14	169.0 (4)	C1—N2—C3—N2'	−95 (8)
C13—C14—C15—C10	0.6 (5)	C10—N2—C3—N2'	75 (7)
C14—C13—O4—C17	6.4 (13)	C1—N2—C3—C2	22.7 (8)
C12—C13—O4—C17	−174.6 (13)	C10—N2—C3—C2	−168.1 (7)
C1—N2'—C10'—C11'	−123 (3)	C1—N2'—C3—O2	−113 (2)
C3—N2'—C10'—C11'	62 (4)	C10'—N2'—C3—O2	64 (3)
C1—N2'—C10'—C15'	74 (4)	C1—N2'—C3—N2	73 (6)
C3—N2'—C10'—C15'	−102 (3)	C10'—N2'—C3—N2	−111 (10)
C15'—C10'—C11'—C12'	−4 (2)	C1—N2'—C3—C2	9 (3)
N2'—C10'—C11'—C12'	−166.4 (17)	C10'—N2'—C3—C2	−175 (3)
C10'—C11'—C12'—C13'	1.4 (19)	O1—C2—C3—O2	−143.51 (15)
C11'—C12'—C13'—C14'	−0.6 (18)	N1—C2—C3—O2	98.64 (16)
C11'—C12'—C13'—O4'	176.8 (10)	O1—C2—C3—N2	93.6 (5)
C12'—C13'—C14'—C15'	2.3 (16)	N1—C2—C3—N2	−24.3 (5)
O4'—C13'—C14'—C15'	−175.4 (8)	O1—C2—C3—N2'	101.0 (17)
C13'—C14'—C15'—C10'	−4.6 (17)	N1—C2—C3—N2'	−16.9 (17)
C11'—C10'—C15'—C14'	6 (2)	C1—N1—C4—C5	64.1 (2)
N2'—C10'—C15'—C14'	168.7 (14)	C2—N1—C4—C5	−98.2 (2)
C12'—C13'—O4'—C17'	7 (4)	C1—N1—C4—C9	−121.2 (2)
C14'—C13'—O4'—C17'	−176 (4)	C2—N1—C4—C9	76.4 (2)
C10—N2—C1—N1	−178.6 (9)	C9—C4—C5—C6	−0.7 (3)
C3—N2—C1—N1	−10.9 (9)	N1—C4—C5—C6	173.91 (17)
C10—N2—C1—N2'	−76 (7)	C4—C5—C6—C7	0.3 (3)
C3—N2—C1—N2'	92 (8)	C16—O3—C7—C8	−175.2 (3)
C10—N2—C1—S1	3.1 (14)	C16—O3—C7—C6	5.4 (4)
C3—N2—C1—S1	170.9 (4)	C5—C6—C7—O3	179.8 (2)
C4—N1—C1—N2	−170.5 (6)	C5—C6—C7—C8	0.4 (3)
C2—N1—C1—N2	−6.9 (6)	O3—C7—C8—C9	−180.0 (3)
C4—N1—C1—N2'	−179.4 (19)	C6—C7—C8—C9	−0.5 (4)
C2—N1—C1—N2'	−15.8 (19)	C7—C8—C9—C4	0.0 (4)
C4—N1—C1—S1	7.7 (3)	C5—C4—C9—C8	0.6 (3)
C2—N1—C1—S1	171.30 (13)	N1—C4—C9—C8	−174.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.99	2.7971 (19)	169
O1—H1···S1ⁱⁱ	0.82	2.40	3.1799 (14)	158

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄S
M_r	346.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.9807 (12), 12.1789 (11), 10.0958 (9)
β (°)	93.815 (1)
V (Å³)	1715.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.49 × 0.35 × 0.34

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.904, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	12720, 3179, 2654
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.03
No. of reflections	3179
No. of parameters	244
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.60

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
O2—H2···O1ⁱ	0.82	1.99	2.7971 (19)	169.1
O1—H1···S1ⁱⁱ	0.82	2.40	3.1799 (14)	158.1

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y−1/2, −z+3/2.

Acknowledgements

Financial support from Henan Normal University and the `Innovation Scientists and Technicians Troop Construction projects of Henan province' (grant No. 2008IRTSTHN002) is gratefully acknowledged. The authors also thank the Physiochemical Analysis Measurement Laboratory, College of Chemistry, Luoyang Normal University, for performing the X-ray analysis.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Lam, P. Y. S., Jadhav, P. K., Eyermann, C. J., Hodge, C. N., Ru, Y., Bacheler, L. T., Meek, J. L., Otto, M. J., Rayner, M. M., Wong, Y. N., Chang, C.-H., Weber, P. C., Jackson, D. A., Sharpe, T. R. & Erickson-Viitanen, S. (1994). Science, 263, 380–384. CrossRef CAS PubMed Web of Science Google Scholar
Lenzen, S. & Ahmad, R. (2001). Ger. Offen. DE10012401. Google Scholar
Perronnet, J. & Teche, A. (1973). US Patent 3905996. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z., Wei, M., Wang, J. & Zhang, G. (2009). Acta Cryst. E65, o2389. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, Z.-F., Zhang, J.-M., Guo, J.-P. & Qu, G.-R. (2007). Acta Cryst. E63, o2821–o2823. Web of Science CSD CrossRef IUCr Journals Google Scholar