3,6,14,17-Tetramethoxy-22,23-diphenyl-1,10,12,21-tetraazahexacyclo[19.2.1.02,7.010,23.012,22.013,18]tetracosa-2(7),3,5,13(18),14,16-hexaene-11,24-di­thione

Yang, Y.

doi:10.1107/S160053681002204X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1673

doi:10.1107/S160053681002204X

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3,6,14,17-Tetramethoxy-22,23-diphenyl-1,10,12,21-tetraazahexacyclo[19.2.1.0^2,7.0^10,23.0^12,22.0^13,18]tetracosa-2(7),3,5,13(18),14,16-hexaene-11,24-dithione

Yan Yang ^a ^*

^aKey Laboratory of Pesticides and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: yanyang20100203@gmail.com

(Received 26 April 2010; accepted 9 June 2010; online 16 June 2010)

The title compound, C₃₆H₃₄N₄O₄S₂, is a thioglycoluril derivative, which bears two phenyl substituents on its convex face and two methoxy substituted o-xylylenes as sidewalls of the molecular clip. There is one half-molecule in the asymmetric unit: a crystallographic twofold axis generates the complete molecule. The non-planar seven-membered rings adopt chair conformations, while the two five-membered rings exhibit envelope conformations and make a dihedral angle of 68.46 (12)°. The O atoms of the methoxy groups are coplanar with the six-membered o-xylylene sidewalls.

Related literature

For related structures, see: Broan et al. (1989 ); Cao et al. (2009 ); Wang et al. (2006 ); Wang & Xi (2009 ); Wu & Sun, (2009 ). For further synthetic details, see: Broan et al. (1989); Wu et al. (2002 ). The rigid concave shape of glycoluril makes it a versatile building block in supramolecular chemistry, see: Gao et al. (2009 ); Rowan et al. (1999 ); Hof et al. (2002 ); Kolbel & Menger (2001 ); Wu et al. (2002); Kang et al. (2004 ).

Experimental

Crystal data

C₃₆H₃₄N₄O₄S₂
M_r = 650.79
Monoclinic, C 2/c
a = 17.9993 (15) Å
b = 12.5069 (11) Å
c = 16.0934 (12) Å
β = 115.961 (3)°
V = 3257.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
13570 measured reflections
3546 independent reflections
2279 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.162
S = 0.98
3546 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002204X/fl2304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002204X/fl2304Isup2.hkl

checkCIF report

Comment top

The rigid concave shape of glycoluril makes it a versatile building block to construct various supramolecular objects (Gao et al., 2009), including molecular clips and molecular baskets (Rowan et al., 1999), molecular capsules (Hof et al., 2002), xerogels (Kolbel & Menger, 2001), the cucurbit[n]uril family (Wu et al., 2002), and anion-binding receptors (Kang et al., 2004). Based on the previous studies (Broan et al., 1989; Cao et al., 2009; Wang et al., 2006; Wang & Xi, 2009; Wu & Sun, 2009), we report here the structure of the title thioglycoluril derivative (Fig. 1), which is a potential receptor in supramolecular chemistry.

There is one half-molecule in the asymmetric unit. The non-planar seven-membered rings adopt chair conformations, while the two five-membered rings have envelope conformation and the dihedral angle between them is 68.46°. The methoxy groups on sidewalls are coplanar with the six-membered o-xylylene sidewalls. The molecule contains three nonclassical intramolecular C—H···S, C—H···O and C—H···N hydrogen bonds, and its crystal structure is stabilized mostly by intermolecular C—H···π interactions (Table 1).

Related literature top

For related structures, see: Broan et al. (1989); Cao et al. (2009); Wang et al. (2006); Wang & Xi (2009); Wu & Sun, (2009). For further synthetic details, see: Broan et al. (1989); Wu et al. (2002). The rigid concave shape of glycoluril makes it a versatile building block, see: Gao et al. (2009); Rowan et al. (1999); Hof et al. (2002); Kolbel & Menger (2001); Wu et al. (2002); Kang et al. (2004).

Experimental top

The thioglycoluril was synthesized according to a literature procedure, see : Broan et al., (1989). Preparation of the title compound: A solution of thioglycoluril (326 mg, 1.00 mmol), paraformaldehyde (120 mg, 4.00 mmol) and 1,4-dimethoxybenzene (304 mg, 2.20 mmol) in TFA (5 ml) was stirred and heated at reflux for 6 h. After rotary evaporation the residue was chromatographed to yield the tile compound (521 mg, 0.80 mmol,80%). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (1:2) solution of the title compound under 293 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing of (I) with C—H···π interactions drawn as dashed lines showing the formation of a one-dimensional chain.

3,6,14,17-Tetramethoxy-22,23-diphenyl-1,10,12,21-tetraazahexacyclo[19.2.1.0^2,7.0^10,23.0^12,22.0^13,18]tetracosa-2(7),3,5,13 (18),14,16-hexaene-11,24-dithione top

Crystal data top

C₃₆H₃₄N₄O₄S₂	F(000) = 1368
M_r = 650.79	D_x = 1.327 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2697 reflections
a = 17.9993 (15) Å	θ = 2.5–21.3°
b = 12.5069 (11) Å	µ = 0.21 mm⁻¹
c = 16.0934 (12) Å	T = 298 K
β = 115.961 (3)°	Block, colorless
V = 3257.3 (5) Å³	0.23 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2279 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.067
Graphite monochromator	θ_max = 27.0°, θ_min = 2.1°
phi and ω scans	h = −22→13
13570 measured reflections	k = −15→15
3546 independent reflections	l = −19→20

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0878P)²] where P = (F_o² + 2F_c²)/3
3546 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₃₆H₃₄N₄O₄S₂	V = 3257.3 (5) Å³
M_r = 650.79	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.9993 (15) Å	µ = 0.21 mm⁻¹
b = 12.5069 (11) Å	T = 298 K
c = 16.0934 (12) Å	0.23 × 0.20 × 0.10 mm
β = 115.961 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2279 reflections with I > 2σ(I)
13570 measured reflections	R_int = 0.067
3546 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 0.98	Δρ_max = 0.29 e Å⁻³
3546 reflections	Δρ_min = −0.24 e Å⁻³
210 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.11451 (4)	0.22118 (5)	0.14339 (5)	0.0528 (3)
N1	0.09215 (11)	0.31734 (13)	0.27979 (13)	0.0335 (5)
N2	−0.00738 (11)	0.34780 (13)	0.14082 (13)	0.0325 (4)
C13	0.07957 (13)	0.50126 (16)	0.32973 (15)	0.0343 (5)
C9	0.16813 (14)	0.27755 (17)	0.35521 (17)	0.0388 (6)
H9A	0.1970	0.3371	0.3949	0.047*
H9B	0.2036	0.2489	0.3294	0.047*
C12	0.03855 (13)	0.39284 (16)	0.29759 (15)	0.0306 (5)
C10	0.06573 (14)	0.29489 (16)	0.18917 (16)	0.0326 (5)
O2	0.06197 (14)	0.16264 (16)	0.57355 (15)	0.0713 (6)
O1	0.24132 (13)	0.08009 (14)	0.37734 (15)	0.0683 (6)
C1	0.15415 (14)	0.19204 (17)	0.41322 (17)	0.0393 (6)
C2	0.10798 (15)	0.21274 (17)	0.46227 (17)	0.0406 (6)
C6	0.19350 (16)	0.09225 (18)	0.42349 (19)	0.0477 (7)
C18	0.13789 (15)	0.53676 (19)	0.30210 (19)	0.0497 (7)
H18	0.1560	0.4916	0.2688	0.060*
C11	−0.06462 (15)	0.31850 (18)	0.04628 (16)	0.0392 (6)
H11A	−0.0343	0.3157	0.0092	0.047*
H11B	−0.1060	0.3742	0.0209	0.047*
C3	0.10368 (17)	0.1344 (2)	0.52320 (19)	0.0512 (7)
C14	0.05429 (16)	0.56979 (18)	0.37978 (18)	0.0463 (7)
H14	0.0150	0.5469	0.3988	0.056*
C4	0.14195 (17)	0.0364 (2)	0.5309 (2)	0.0578 (8)
H4	0.1379	−0.0156	0.5701	0.069*
C17	0.16966 (18)	0.6394 (2)	0.3237 (2)	0.0655 (9)
H17	0.2086	0.6631	0.3045	0.079*
C5	0.18588 (18)	0.0156 (2)	0.4811 (2)	0.0564 (8)
H5	0.2108	−0.0508	0.4863	0.068*
C15	0.0865 (2)	0.6717 (2)	0.4019 (2)	0.0638 (9)
H15	0.0693	0.7170	0.4360	0.077*
C16	0.1438 (2)	0.7055 (2)	0.3733 (2)	0.0731 (10)
H16	0.1654	0.7742	0.3878	0.088*
C7	0.2729 (2)	−0.0224 (2)	0.3750 (3)	0.0859 (11)
H7A	0.2924	−0.0550	0.4348	0.129*
H7B	0.3178	−0.0162	0.3583	0.129*
H7C	0.2301	−0.0658	0.3302	0.129*
C8	0.0599 (2)	0.0907 (3)	0.6401 (2)	0.0865 (11)
H8A	0.0241	0.0319	0.6094	0.130*
H8B	0.0396	0.1269	0.6787	0.130*
H8C	0.1146	0.0643	0.6775	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0520 (5)	0.0520 (4)	0.0612 (5)	0.0130 (3)	0.0311 (4)	−0.0081 (3)
N1	0.0300 (11)	0.0293 (9)	0.0435 (12)	0.0043 (7)	0.0181 (9)	0.0014 (8)
N2	0.0341 (11)	0.0273 (9)	0.0390 (11)	0.0020 (8)	0.0189 (9)	−0.0016 (8)
C13	0.0316 (13)	0.0300 (11)	0.0397 (13)	−0.0029 (9)	0.0141 (10)	0.0006 (9)
C9	0.0268 (13)	0.0385 (13)	0.0466 (14)	0.0035 (10)	0.0118 (11)	0.0042 (10)
C12	0.0317 (12)	0.0264 (10)	0.0391 (12)	0.0013 (9)	0.0205 (10)	0.0006 (9)
C10	0.0327 (13)	0.0270 (11)	0.0395 (14)	−0.0012 (9)	0.0170 (11)	0.0011 (9)
O2	0.0922 (16)	0.0662 (13)	0.0746 (14)	0.0174 (11)	0.0543 (13)	0.0311 (11)
O1	0.0756 (15)	0.0481 (11)	0.0968 (17)	0.0248 (10)	0.0521 (13)	0.0162 (10)
C1	0.0328 (14)	0.0343 (12)	0.0433 (14)	0.0000 (10)	0.0097 (11)	0.0030 (10)
C2	0.0390 (14)	0.0331 (12)	0.0430 (14)	−0.0015 (10)	0.0118 (12)	0.0037 (10)
C6	0.0452 (16)	0.0364 (13)	0.0582 (17)	0.0053 (11)	0.0197 (13)	0.0014 (11)
C18	0.0428 (16)	0.0428 (14)	0.0692 (19)	−0.0048 (11)	0.0300 (14)	0.0017 (12)
C11	0.0397 (14)	0.0408 (13)	0.0357 (13)	0.0020 (10)	0.0153 (11)	−0.0017 (10)
C3	0.0549 (18)	0.0474 (15)	0.0536 (17)	−0.0009 (13)	0.0259 (14)	0.0083 (12)
C14	0.0582 (17)	0.0334 (13)	0.0518 (16)	−0.0035 (11)	0.0284 (14)	−0.0037 (11)
C4	0.063 (2)	0.0437 (15)	0.0596 (18)	0.0013 (13)	0.0207 (16)	0.0190 (13)
C17	0.0486 (18)	0.0531 (17)	0.091 (2)	−0.0183 (14)	0.0267 (17)	0.0117 (16)
C5	0.065 (2)	0.0345 (14)	0.0639 (19)	0.0073 (12)	0.0226 (16)	0.0073 (13)
C15	0.090 (2)	0.0359 (14)	0.0624 (19)	−0.0065 (15)	0.0304 (17)	−0.0115 (13)
C16	0.084 (3)	0.0387 (16)	0.080 (2)	−0.0232 (16)	0.021 (2)	−0.0042 (15)
C7	0.112 (3)	0.055 (2)	0.113 (3)	0.0199 (19)	0.070 (3)	−0.0035 (18)
C8	0.099 (3)	0.095 (3)	0.076 (2)	0.009 (2)	0.048 (2)	0.036 (2)

Geometric parameters (Å, º) top

S1—C10	1.652 (2)	C6—C5	1.381 (4)
N1—C10	1.351 (3)	C18—C17	1.386 (4)
N1—C9	1.462 (3)	C18—H18	0.9300
N1—C12	1.465 (3)	C11—C2ⁱ	1.511 (3)
N2—C10	1.371 (3)	C11—H11A	0.9700
N2—C12ⁱ	1.450 (3)	C11—H11B	0.9700
N2—C11	1.462 (3)	C3—C4	1.384 (4)
C13—C18	1.381 (3)	C14—C15	1.381 (3)
C13—C14	1.382 (3)	C14—H14	0.9300
C13—C12	1.522 (3)	C4—C5	1.375 (4)
C9—C1	1.511 (3)	C4—H4	0.9300
C9—H9A	0.9700	C17—C16	1.364 (4)
C9—H9B	0.9700	C17—H17	0.9300
C12—N2ⁱ	1.450 (3)	C5—H5	0.9300
C12—C12ⁱ	1.553 (4)	C15—C16	1.369 (4)
O2—C3	1.370 (3)	C15—H15	0.9300
O2—C8	1.412 (3)	C16—H16	0.9300
O1—C6	1.369 (3)	C7—H7A	0.9600
O1—C7	1.410 (3)	C7—H7B	0.9600
C1—C2	1.398 (3)	C7—H7C	0.9600
C1—C6	1.409 (3)	C8—H8A	0.9600
C2—C3	1.412 (3)	C8—H8B	0.9600
C2—C11ⁱ	1.511 (3)	C8—H8C	0.9600

C10—N1—C9	125.79 (19)	N2—C11—H11A	108.6
C10—N1—C12	113.23 (17)	C2ⁱ—C11—H11A	108.6
C9—N1—C12	120.91 (18)	N2—C11—H11B	108.6
C10—N2—C12ⁱ	111.24 (18)	C2ⁱ—C11—H11B	108.6
C10—N2—C11	122.26 (18)	H11A—C11—H11B	107.6
C12ⁱ—N2—C11	120.09 (18)	O2—C3—C4	123.7 (2)
C18—C13—C14	118.6 (2)	O2—C3—C2	116.3 (2)
C18—C13—C12	120.1 (2)	C4—C3—C2	120.0 (3)
C14—C13—C12	121.1 (2)	C15—C14—C13	121.0 (3)
N1—C9—C1	113.92 (19)	C15—C14—H14	119.5
N1—C9—H9A	108.8	C13—C14—H14	119.5
C1—C9—H9A	108.8	C5—C4—C3	120.4 (2)
N1—C9—H9B	108.8	C5—C4—H4	119.8
C1—C9—H9B	108.8	C3—C4—H4	119.8
H9A—C9—H9B	107.7	C16—C17—C18	120.0 (3)
N2ⁱ—C12—N1	111.61 (16)	C16—C17—H17	120.0
N2ⁱ—C12—C13	112.90 (18)	C18—C17—H17	120.0
N1—C12—C13	112.20 (18)	C4—C5—C6	120.8 (2)
N2ⁱ—C12—C12ⁱ	103.2 (2)	C4—C5—H5	119.6
N1—C12—C12ⁱ	100.82 (17)	C6—C5—H5	119.6
C13—C12—C12ⁱ	115.23 (12)	C16—C15—C14	119.4 (3)
N1—C10—N2	108.02 (18)	C16—C15—H15	120.3
N1—C10—S1	126.35 (17)	C14—C15—H15	120.3
N2—C10—S1	125.57 (17)	C17—C16—C15	120.7 (3)
C3—O2—C8	119.2 (2)	C17—C16—H16	119.7
C6—O1—C7	118.2 (2)	C15—C16—H16	119.7
C2—C1—C6	119.4 (2)	O1—C7—H7A	109.5
C2—C1—C9	121.2 (2)	O1—C7—H7B	109.5
C6—C1—C9	119.2 (2)	H7A—C7—H7B	109.5
C1—C2—C3	119.4 (2)	O1—C7—H7C	109.5
C1—C2—C11ⁱ	121.4 (2)	H7A—C7—H7C	109.5
C3—C2—C11ⁱ	119.2 (2)	H7B—C7—H7C	109.5
O1—C6—C5	123.9 (2)	O2—C8—H8A	109.5
O1—C6—C1	116.0 (2)	O2—C8—H8B	109.5
C5—C6—C1	120.0 (3)	H8A—C8—H8B	109.5
C13—C18—C17	120.3 (3)	O2—C8—H8C	109.5
C13—C18—H18	119.8	H8A—C8—H8C	109.5
C17—C18—H18	119.8	H8B—C8—H8C	109.5
N2—C11—C2ⁱ	114.50 (19)

C10—N1—C9—C1	−106.3 (3)	C7—O1—C6—C5	11.7 (4)
C12—N1—C9—C1	77.1 (3)	C7—O1—C6—C1	−171.6 (3)
C10—N1—C12—N2ⁱ	122.1 (2)	C2—C1—C6—O1	−176.5 (2)
C9—N1—C12—N2ⁱ	−60.9 (2)	C9—C1—C6—O1	−1.2 (3)
C10—N1—C12—C13	−110.1 (2)	C2—C1—C6—C5	0.4 (4)
C9—N1—C12—C13	66.9 (2)	C9—C1—C6—C5	175.7 (2)
C10—N1—C12—C12ⁱ	13.1 (2)	C14—C13—C18—C17	−0.5 (4)
C9—N1—C12—C12ⁱ	−169.92 (18)	C12—C13—C18—C17	173.8 (2)
C18—C13—C12—N2ⁱ	155.7 (2)	C10—N2—C11—C2ⁱ	70.0 (3)
C14—C13—C12—N2ⁱ	−30.1 (3)	C12ⁱ—N2—C11—C2ⁱ	−79.4 (2)
C18—C13—C12—N1	28.6 (3)	C8—O2—C3—C4	2.6 (4)
C14—C13—C12—N1	−157.3 (2)	C8—O2—C3—C2	−175.9 (3)
C18—C13—C12—C12ⁱ	−86.0 (3)	C1—C2—C3—O2	175.8 (2)
C14—C13—C12—C12ⁱ	88.1 (3)	C11ⁱ—C2—C3—O2	−2.3 (4)
C9—N1—C10—N2	−179.57 (19)	C1—C2—C3—C4	−2.8 (4)
C12—N1—C10—N2	−2.7 (2)	C11ⁱ—C2—C3—C4	179.0 (2)
C9—N1—C10—S1	−2.1 (3)	C18—C13—C14—C15	0.0 (4)
C12—N1—C10—S1	174.75 (16)	C12—C13—C14—C15	−174.3 (2)
C12ⁱ—N2—C10—N1	−10.2 (2)	O2—C3—C4—C5	−177.0 (3)
C11—N2—C10—N1	−162.05 (19)	C2—C3—C4—C5	1.5 (4)
C12ⁱ—N2—C10—S1	172.29 (15)	C13—C18—C17—C16	0.6 (4)
C11—N2—C10—S1	20.5 (3)	C3—C4—C5—C6	0.8 (4)
N1—C9—C1—C2	−61.3 (3)	O1—C6—C5—C4	174.9 (2)
N1—C9—C1—C6	123.5 (2)	C1—C6—C5—C4	−1.8 (4)
C6—C1—C2—C3	1.8 (4)	C13—C14—C15—C16	0.5 (4)
C9—C1—C2—C3	−173.4 (2)	C18—C17—C16—C15	−0.2 (5)
C6—C1—C2—C11ⁱ	180.0 (2)	C14—C15—C16—C17	−0.4 (5)
C9—C1—C2—C11ⁱ	4.8 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ⁱ	0.97	2.70	3.540	145
C11—H11A···O2ⁱ	0.97	2.26	2.757 (3)	111
C14—H14···N2ⁱ	0.93	2.56	2.879 (3)	101
C18—H18···N1	0.93	2.51	2.842 (3)	102
C9—H9B···S1	0.97	2.73	3.189 (3)	110
C9—H9B···O1	0.97	2.25	2.748 (3)	111

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₆H₃₄N₄O₄S₂
M_r	650.79
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	17.9993 (15), 12.5069 (11), 16.0934 (12)
β (°)	115.961 (3)
V (Å³)	3257.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.23 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13570, 3546, 2279
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.162, 0.98
No. of reflections	3546
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ⁱ	0.971	2.702	3.540	144.73
C11—H11A···O2ⁱ	0.97	2.26	2.757 (3)	111
C14—H14···N2ⁱ	0.93	2.56	2.879 (3)	101
C18—H18···N1	0.93	2.51	2.842 (3)	102
C9—H9B···S1	0.97	2.73	3.189 (3)	110
C9—H9B···O1	0.97	2.25	2.748 (3)	111

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

The author thanks Professor An-Xin Wu for technical assistance and Dr Meng Xiang-Gao for the data collection.

References

Broan, C. J., Butler, A. R., Reed, D. & Sadler, I. H. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 731–740. CrossRef Google Scholar
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Cao, L., Ding, J., Yin, G., Gao, M., Li, Y. & Wu, A. (2009). Synlett, pp. 1445–1448. Google Scholar
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Volume 66| Part 7| July 2010| Page o1673

doi:10.1107/S160053681002204X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,6,14,17-Tetra­meth­oxy-22,23-di­phenyl-1,10,12,21-tetra­azahexa­cyclo[19.2.1.02,7.010,23.012,22.013,18]tetracosa-2(7),3,5,13(18),14,16-hexa­ene-11,24-di­thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,6,14,17-Tetramethoxy-22,23-diphenyl-1,10,12,21-tetraazahexacyclo[19.2.1.0^2,7.0^10,23.0^12,22.0^13,18]tetracosa-2(7),3,5,13(18),14,16-hexaene-11,24-dithione