A series of three (E)-2-alkyl­idene-1,4-di-p-tosyl-1,2,3,4-tetra­hydro­quinoxaline compounds

The three title quinoxaline derivatives, (E)-2-(4-methylbenzyl­i­dene)-1,4-di-p-tosyl-1,2,3,4-tetra­hy­dro­quin­ox­a­line, C₃₀H₂₈N₂O₄S₂, (II), (E)-2-(4-methoxy­ben­zyl­idene)-1,4-di-p-tosyl-1,2,3,4-tetra­hy­dro­quin­ox­a­line, C₃₀H₂₈N₂O₅S₂, (III), and (E)-2-(3-chloro­ben­zyl­idene)-1,4-di-p-tosyl-1,2,3,4-tetra­hydro­quin­ox­a­line, C₂₉H₂₅ClN₂O₄S₂, (IV), were synthesized by palladium-catalyzed hetero-annulation. The E configuration of the exocyclic double bond in the three compounds has been established by the present X-ray study. The saturated part of the quinoxaline moiety in all three compounds assumes a distorted chair conformation. The numerical descriptors indicate a high degree of isostructurality between compounds (II) and (III), but no isostructurality with compound (IV).

S1. Comment

The quinoxaline system (I) and its derivatives have been successfully used in medicinal chemistry, particularly as synthetic precursors of antihypertensives, analgesics and neurotransmitter antagonists (Fuente et al., 2000; Kher et al., 1995; Manca et al., 1992). Many of these compounds also exhibit anticancer activity in vitro (Loriga et al., 1995). Although some preliminary information concerning the substituent directing effects of quinoxaline derivatives is available (Porter, 1984), to our knowledge, no X-ray crystal structure of N-substituted quinoxaline has been reported previously. As part of an ongoing program on the synthesis and characterization of quinoxaline-containing heterocyclic systems, we synthesized three 2-alkylidene-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxalines via palladium-catalyzed reaction between N-(prop-2-ynyl)-N,N^'-1,2-phenylene-di-p-tosylamide and aryl iodides. To establish the regio-and stereospecificities of the reaction and to build up a hierarchy for such systems, X-ray analyses of 2-(4-methylbenzylidene)-1,4-di-p-tosyl- 1,2,3,4-tetrahydroquinoxaline, (II), 2-(4-methoxybenzylidene)-1,4-di- p-tosyl-1,2,3,4-tetrahydroquinoxaline, (III), and 2-(3-chlorobenzylidene)-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline, (IV), were undertaken. \sch

The title compounds (Figs. 1, 2 and 3) consist of a quinoxaline system with two p-tosyl and one substituted phenylmethylidene group at the 1, 4 and 2 positions, respectively. The E configurations of the molecules of (II), (III) and (IV) are established by the torsion angle N1—C8—C9—C10 of 174.7 (2) for (II), 176.8 (2) for (III) and 178.4 (3)° for (IV). As expected, the pyrazine ring B(N1—C1—C6—N2—C7—C8) fused to the phenyl ring A(C1—C6) in the compounds deviates significantly from planarity with the ring puckering parameters (Cremer & Pople, 1975) Q = 0.410 (2), 0.411 (2) and 0.404 (3) Å, θ = 133.2 (3), 134.8 (3) and 47.1 (4)°, and ϕ = 82.9 (4), 88.0 (4) and -90.8 (5)° for (II), (III) and (IV), respectively. The heterocyclic ring (C₄N₂) in all three compounds assumes a distorted chair conformation with the C1 and C7 atoms deviating by -0.117 (2) and 0.566 (2) Å in (II), -0.147 (2) and 0.560 (2) Å in (III), and -0.127 (3) and 0.541 (3) Å in (IV), respectively, from the least-squares plane through the remaining endocyclic atoms.

A comparision of the molecular geometries of (II), (III) and (IV) reveals the similarity of all bond lengths among the three compounds (Tables 1, 3 and 5). The two N atoms of the pyrazine ring (N1 and N2) with the sum of bond angles deviating significantly from 360° [346.8 (2) and 350.0 (2)° in (II), 345.4 (2) and 347.3 (2)° in (III), and 349.7 (2) and 348.4 (2)° in (IV)] indicate pyramidal distortions and occupy axial orientations with respect to their substituents (Tables 1, 3 and 5). The geometry at the S atoms in the compounds deviate significantly from that of regular tetrahedron, with the largest deviation in the O—S—O angle (Tables 1, 3 and 5). The widening of the O—S—O angle [119.7 (1)–120.3 (2)°] from the ideal tetrahedral value is presumably the result of the repulsive interaction between the short S═O bonds. The tosyl groups in (II), (III) and (IV) adopt folded conformations, in which the phenyl rings C [atoms: C17—C22 in (II) and (III); C16—C21 in (IV)] and D [atoms: C24—C29 in (II) and (III); C23—C28 in (IV)] shield the quinoxaline moiety (AB). The dihedral angles between A/C and A/D are similar in all the three structures [53.5 (1) and 55.8 (1)° in (II), 52.2 (1) and 53.2 (1)° in (III), 50.5 (1) and 57.1 (1)° in (IV)].

In compounds (II) and (IV), the phenyl rings C and D are almost parallel to each other [the dihedral angle C/D 2.3 (1)° in (II) and 7.7 (1)° in (IV)] whereas in compound (III) the C and D rings are inclined by 27.2 (1)°. This is probably to minimize the steric hindrance introduced by the methoxyphenyl group in (III). The S—O [1.417 (3)–1.439 (3) Å], S—C [1.749 (2)–1.762 (2) Å] and S—N [1.673 (2)–1.707 (2) Å] bond distances (Tables 1, 3 and 5) are consistent with the corresponding values reported in International Tables for X-ray Crystallography (Allen et al., 1992). The lack of π bonding in the branches among the phenyl rings precludes any possible π conjugation across the whole molecule in (II), (III) and (IV). The aromatic nature of the rings is therefore localized within the rings and on their direct substituents.

The identical space groups and the similarity of lattice parameters of (II), (III) and (IV) suggest some degree of isostructurality among the compounds. The results of calculation (Table 7) of the unit-cell similarity descriptor Π (Ka^'lma^'n et al., 1993), the asphericity index A (Rutherford, 1997), the isostructurality index I_i (Ka^'lma^'n et al., 1993) and the volumetric isostructurality index I_v (Fa^'via^'n & Ka^'lma^'n, 1999) reveal a high degree of isostructurality between compounds (II) and (III).

The volumetric index of isostructurality between compounds (II) and (III) amounts to 82% for the whole unit cell, with four molecules indicating significant packing similarity of the related structures. The large values of the asphericity index (A) and the isostructurality index, I_i(37), between (II)-(IV) and (III)-(IV) (Table 7) indicate that the compound (IV) is not isostructural with compound (II) or (III). This is probably a consequence of the exchange of cell axis lengths in compound (IV) compared to those in (II) and (III), and the different positions of substituents in the phenylmethylidene moiety [4-methyl in (II), 4-methoxy in (III) and 3-chloro in (IV)] of the structures.

In all three compounds [(II), (III) and (IV)] the crystal packing is stabilized by weak C—H···O intermolecular interactions (Tables 2, 4 and 6) involving the sulfonyl and methoxy O atoms.

S2. Experimental

The compounds (II), (III) and (IV) were synthesized in the following way. A mixture of aryl iodide [4-methyliodobenzene for (II), 4-methoxyiodobenzene for (III) and 3-chloroiodobenzene for (IV)] (1.15 mmol), palladium(II) acetate (5 mol%), anhydrous potassium carbonate (4.40 mmol) and tetrabutylammonium bromide (4.40 mmol) was stirred in 10 ml of dimethylformamide(DMF) for half an hour. The acetylenic compound, N-(prop-2-ynyl)-N,N^'-1,2-phenylene-di-p-tosylamide (0.88 mmol) was added to it and the mixture was further stirred for 24 h at room temperature. After usual workup, the crude product purified by column chromatography through silica gel using chloroform as eluant yielded the title compounds (II), (III) and (IV). Single crystals of (II), (III) and (IV) suitable for X-ray analyses were obtained from chloroform/light petroleum (333–353 K) mixture (1:1). Compound (II): m.p. 428 (1) K, analysis found: C 66.43, H 5.23, N 4.87%; calculated for C₃₀H₂₈N₂S₂O₄: C 66.17, H 5.14, N 5.14%. Compound (III): m.p. 425 (1) K, analysis found: C 64.04, H 5.06, N 4.88%; calculated for C₃₀H₂₈N₂S₂O₅: C 64.28, H 5.14, N 5.10%. Compound (IV): m.p. 418 (1) K, analysis found C 61.94, N 4.36, N 4.78%; calculated for C₂₉H₂₅N₂S₂O₄Cl: C 61.65, H 4.42, N 4.46%.

Computing details

For all compounds, data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: MULTAN 88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL97 and PARST 95 (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (II) showing 50% probability displacement ellipsoids.
	Fig. 2. The molecular structure of (III) showing 50% probability displacement ellipsoids.
	Fig. 3. The molecular structure of (IV) showing 50% probability displacement ellipsoids.

(II) 2-[(4-methylphenyl)methylidene]-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline

Crystal data

C30H28N2O4S2	Dx = 1.290 Mg m^−3
Mr = 544.66	Melting point: 428(1) K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.559 (4) Å	Cell parameters from 37 reflections
b = 11.658 (4) Å	θ = 1.9–16.3°
c = 23.169 (7) Å	µ = 0.23 mm^−1
β = 100.54 (3)°	T = 293 K
V = 2803.9 (17) Å^3	Block, colourless
Z = 4	0.64 × 0.52 × 0.48 mm
F(000) = 1144

Data collection

Siemens P4 diffractometer	3664 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −1→12
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −1→13
Tmin = 0.866, Tmax = 0.896	l = −27→27
6386 measured reflections	3 standard reflections every 97 reflections
4923 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0604P)^2 + 0.6663P] where P = (Fo^2 + 2Fc^2)/3
4923 reflections	(Δ/σ)max = 0.003
346 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.30086 (6)	0.25747 (5)	0.15874 (4)	0.0788 (2)
N1	0.14136 (17)	0.23239 (15)	0.15816 (9)	0.0638 (5)
O1	0.30516 (18)	0.33353 (16)	0.11065 (12)	0.1101 (8)
O2	0.35635 (19)	0.2907 (2)	0.21676 (11)	0.1189 (9)
S2	−0.18201 (5)	0.01590 (5)	0.11171 (3)	0.06174 (19)
N2	−0.02264 (16)	0.03468 (14)	0.13007 (8)	0.0548 (4)
O3	−0.21918 (16)	−0.05499 (16)	0.15587 (9)	0.0875 (6)
O4	−0.20392 (16)	−0.02169 (14)	0.05199 (8)	0.0783 (5)
C1	0.1090 (2)	0.1597 (2)	0.20364 (10)	0.0628 (6)
C2	0.1501 (3)	0.1889 (3)	0.26257 (13)	0.0868 (9)
H2	0.1956	0.2566	0.2722	0.104*
C3	0.1239 (3)	0.1186 (4)	0.30619 (14)	0.1105 (12)
H3	0.1504	0.1396	0.3453	0.133*
C4	0.0584 (3)	0.0169 (4)	0.29266 (14)	0.1076 (11)
H4	0.0454	−0.0325	0.3225	0.129*
C5	0.0122 (3)	−0.0115 (3)	0.23484 (12)	0.0822 (8)
H5	−0.0328	−0.0797	0.2259	0.099*
C6	0.0326 (2)	0.0615 (2)	0.18956 (10)	0.0593 (5)
C7	0.0387 (2)	0.09056 (17)	0.08535 (10)	0.0561 (5)
H7A	−0.0179	0.0853	0.0474	0.067*
H7B	0.1183	0.0510	0.0827	0.067*
C8	0.06717 (19)	0.21462 (17)	0.10031 (10)	0.0557 (5)
C9	0.0305 (2)	0.30615 (18)	0.06680 (11)	0.0638 (6)
H9	0.0497	0.3769	0.0848	0.077*
C10	−0.0360 (2)	0.31014 (18)	0.00546 (11)	0.0622 (6)
C11	−0.0157 (3)	0.2325 (2)	−0.03727 (12)	0.0813 (8)
H11	0.0436	0.1735	−0.0274	0.098*
C12	−0.0820 (4)	0.2414 (3)	−0.09396 (13)	0.0945 (9)
H12	−0.0670	0.1878	−0.1217	0.113*
C13	−0.1707 (3)	0.3282 (3)	−0.11085 (12)	0.0834 (8)
C14	−0.1890 (3)	0.4070 (2)	−0.06887 (13)	0.0768 (7)
H14	−0.2474	0.4666	−0.0791	0.092*
C15	−0.1227 (2)	0.39927 (19)	−0.01235 (12)	0.0686 (6)
H15	−0.1357	0.4547	0.0148	0.082*
C16	−0.2420 (4)	0.3373 (4)	−0.17354 (13)	0.1192 (12)
H16A	−0.1909	0.3037	−0.1994	0.179*
H16B	−0.2577	0.4165	−0.1836	0.179*
H16C	−0.3226	0.2973	−0.1774	0.179*
C17	0.36745 (19)	0.12593 (19)	0.14356 (10)	0.0576 (5)
C18	0.4110 (2)	0.0497 (2)	0.18827 (11)	0.0711 (6)
H18	0.4082	0.0689	0.2270	0.085*
C19	0.4583 (3)	−0.0543 (2)	0.17511 (13)	0.0787 (7)
H19	0.4873	−0.1056	0.2054	0.094*
C20	0.4644 (2)	−0.0855 (2)	0.11845 (13)	0.0708 (7)
C21	0.4215 (2)	−0.0086 (2)	0.07457 (12)	0.0749 (7)
H21	0.4251	−0.0280	0.0360	0.090*
C22	0.3731 (2)	0.0970 (2)	0.08624 (11)	0.0686 (6)
H22	0.3446	0.1483	0.0559	0.082*
C23	0.5167 (3)	−0.2009 (3)	0.10473 (18)	0.1132 (12)
H23A	0.5571	−0.2373	0.1406	0.170*
H23B	0.5789	−0.1906	0.0797	0.170*
H23C	0.4475	−0.2481	0.0852	0.170*
C24	−0.25481 (19)	0.15097 (19)	0.11401 (10)	0.0572 (5)
C25	−0.2946 (2)	0.2117 (2)	0.06328 (11)	0.0696 (6)
H25	−0.2838	0.1819	0.0273	0.084*
C26	−0.3511 (2)	0.3180 (2)	0.06639 (14)	0.0798 (7)
H26	−0.3788	0.3589	0.0319	0.096*
C27	−0.3675 (2)	0.3649 (2)	0.11888 (16)	0.0812 (8)
C28	−0.3270 (3)	0.3020 (3)	0.16894 (15)	0.0987 (10)
H28	−0.3367	0.3323	0.2050	0.118*
C29	−0.2722 (3)	0.1950 (3)	0.16707 (12)	0.0840 (8)
H29	−0.2473	0.1530	0.2014	0.101*
C30	−0.4278 (3)	0.4826 (2)	0.1217 (2)	0.1225 (14)
H30A	−0.4716	0.5044	0.0832	0.184*
H30B	−0.3617	0.5376	0.1357	0.184*
H30C	−0.4883	0.4802	0.1480	0.184*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0496 (3)	0.0506 (3)	0.1297 (6)	−0.0030 (3)	−0.0005 (3)	−0.0133 (4)
N1	0.0488 (10)	0.0500 (10)	0.0879 (13)	0.0041 (8)	0.0004 (9)	−0.0115 (10)
O1	0.0652 (11)	0.0557 (10)	0.208 (2)	−0.0022 (8)	0.0202 (13)	0.0383 (13)
O2	0.0637 (11)	0.1138 (16)	0.167 (2)	−0.0072 (11)	−0.0120 (12)	−0.0788 (16)
S2	0.0455 (3)	0.0496 (3)	0.0859 (4)	−0.0014 (2)	0.0009 (3)	0.0042 (3)
N2	0.0453 (9)	0.0484 (9)	0.0682 (11)	0.0009 (7)	0.0037 (8)	0.0032 (8)
O3	0.0571 (10)	0.0759 (11)	0.1266 (15)	−0.0089 (8)	0.0090 (10)	0.0376 (11)
O4	0.0651 (10)	0.0660 (10)	0.0942 (12)	0.0022 (8)	−0.0107 (9)	−0.0255 (9)
C1	0.0485 (12)	0.0615 (13)	0.0738 (15)	0.0158 (10)	−0.0007 (10)	−0.0098 (12)
C2	0.0697 (16)	0.097 (2)	0.0852 (19)	0.0249 (15)	−0.0079 (14)	−0.0256 (17)
C3	0.094 (2)	0.161 (4)	0.0707 (19)	0.041 (2)	−0.0014 (17)	−0.011 (2)
C4	0.087 (2)	0.158 (4)	0.077 (2)	0.022 (2)	0.0107 (16)	0.024 (2)
C5	0.0634 (15)	0.099 (2)	0.0811 (18)	0.0086 (14)	0.0062 (13)	0.0202 (16)
C6	0.0448 (11)	0.0621 (13)	0.0689 (14)	0.0130 (10)	0.0053 (10)	0.0018 (11)
C7	0.0511 (11)	0.0451 (11)	0.0709 (13)	0.0002 (9)	0.0081 (10)	−0.0016 (10)
C8	0.0457 (11)	0.0456 (11)	0.0746 (14)	0.0012 (9)	0.0082 (10)	−0.0034 (10)
C9	0.0569 (13)	0.0430 (11)	0.0928 (17)	0.0030 (10)	0.0173 (12)	0.0004 (11)
C10	0.0630 (13)	0.0457 (11)	0.0811 (15)	0.0022 (10)	0.0216 (12)	0.0091 (11)
C11	0.103 (2)	0.0639 (15)	0.0847 (18)	0.0247 (14)	0.0369 (16)	0.0159 (14)
C12	0.136 (3)	0.0761 (18)	0.0794 (19)	0.0126 (18)	0.0405 (18)	0.0097 (15)
C13	0.096 (2)	0.0749 (17)	0.0808 (17)	−0.0080 (15)	0.0207 (15)	0.0211 (15)
C14	0.0700 (15)	0.0600 (15)	0.100 (2)	0.0043 (12)	0.0138 (14)	0.0225 (14)
C15	0.0670 (14)	0.0452 (12)	0.0950 (18)	0.0015 (11)	0.0187 (13)	0.0066 (12)
C16	0.135 (3)	0.134 (3)	0.084 (2)	−0.016 (2)	0.008 (2)	0.026 (2)
C17	0.0415 (11)	0.0552 (12)	0.0718 (14)	−0.0002 (9)	−0.0013 (10)	0.0017 (11)
C18	0.0680 (15)	0.0767 (16)	0.0631 (14)	0.0133 (13)	−0.0022 (11)	0.0047 (12)
C19	0.0709 (16)	0.0693 (16)	0.0904 (19)	0.0158 (13)	0.0003 (13)	0.0224 (14)
C20	0.0464 (12)	0.0608 (14)	0.104 (2)	−0.0007 (11)	0.0095 (12)	−0.0074 (14)
C21	0.0590 (14)	0.0906 (19)	0.0753 (16)	0.0020 (13)	0.0126 (12)	−0.0143 (15)
C22	0.0563 (13)	0.0786 (16)	0.0684 (15)	0.0013 (12)	0.0046 (11)	0.0167 (13)
C23	0.0759 (18)	0.0706 (18)	0.192 (4)	0.0041 (15)	0.022 (2)	−0.032 (2)
C24	0.0405 (11)	0.0578 (12)	0.0713 (14)	0.0021 (9)	0.0053 (10)	0.0020 (11)
C25	0.0626 (14)	0.0661 (14)	0.0788 (16)	0.0094 (12)	0.0092 (12)	0.0049 (13)
C26	0.0631 (15)	0.0665 (16)	0.108 (2)	0.0090 (12)	0.0105 (14)	0.0177 (15)
C27	0.0462 (13)	0.0610 (15)	0.136 (3)	0.0024 (11)	0.0147 (14)	−0.0119 (17)
C28	0.088 (2)	0.103 (2)	0.105 (2)	0.0233 (18)	0.0190 (17)	−0.0307 (19)
C29	0.0805 (18)	0.098 (2)	0.0742 (17)	0.0228 (16)	0.0149 (13)	−0.0001 (15)
C30	0.0707 (18)	0.0667 (17)	0.227 (4)	0.0082 (15)	0.018 (2)	−0.027 (2)

Geometric parameters (Å, º)

S1—O2	1.419 (2)	C13—C16	1.512 (4)
S1—O1	1.431 (2)	C14—C15	1.370 (4)
S1—N1	1.707 (2)	C14—H14	0.9300
S1—C17	1.749 (2)	C15—H15	0.9300
N1—C8	1.439 (3)	C16—H16A	0.9600
N1—C1	1.441 (3)	C16—H16B	0.9600
S2—O3	1.4250 (18)	C16—H16C	0.9600
S2—O4	1.4293 (18)	C17—C18	1.378 (3)
S2—N2	1.6729 (18)	C17—C22	1.382 (3)
S2—C24	1.757 (2)	C18—C19	1.368 (4)
N2—C6	1.430 (3)	C18—H18	0.9300
N2—C7	1.471 (3)	C19—C20	1.375 (4)
C1—C2	1.397 (4)	C19—H19	0.9300
C1—C6	1.405 (3)	C20—C21	1.370 (4)
C2—C3	1.368 (5)	C20—C23	1.510 (4)
C2—H2	0.9300	C21—C22	1.378 (4)
C3—C4	1.379 (5)	C21—H21	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.380 (4)	C23—H23A	0.9600
C4—H4	0.9300	C23—H23B	0.9600
C5—C6	1.398 (3)	C23—H23C	0.9600
C5—H5	0.9300	C24—C25	1.371 (3)
C7—C8	1.505 (3)	C24—C29	1.375 (3)
C7—H7A	0.9700	C25—C26	1.383 (4)
C7—H7B	0.9700	C25—H25	0.9300
C8—C9	1.335 (3)	C26—C27	1.373 (4)
C9—C10	1.466 (3)	C26—H26	0.9300
C9—H9	0.9300	C27—C28	1.373 (4)
C10—C11	1.387 (3)	C27—C30	1.519 (4)
C10—C15	1.396 (3)	C28—C29	1.378 (4)
C11—C12	1.374 (4)	C28—H28	0.9300
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.386 (4)	C30—H30A	0.9600
C12—H12	0.9300	C30—H30B	0.9600
C13—C14	1.378 (4)	C30—H30C	0.9600
O2—S1—O1	120.14 (15)	C15—C14—C13	121.2 (2)
O2—S1—N1	106.87 (13)	C15—C14—H14	119.4
O1—S1—N1	105.77 (11)	C13—C14—H14	119.4
O2—S1—C17	108.57 (12)	C14—C15—C10	121.6 (2)
O1—S1—C17	108.38 (13)	C14—C15—H15	119.2
N1—S1—C17	106.30 (9)	C10—C15—H15	119.2
C8—N1—C1	115.81 (18)	C13—C16—H16A	109.5
C8—N1—S1	113.60 (16)	C13—C16—H16B	109.5
C1—N1—S1	117.41 (14)	H16A—C16—H16B	109.5
O3—S2—O4	120.01 (12)	C13—C16—H16C	109.5
O3—S2—N2	106.84 (10)	H16A—C16—H16C	109.5
O4—S2—N2	105.28 (10)	H16B—C16—H16C	109.5
O3—S2—C24	108.57 (12)	C18—C17—C22	119.9 (2)
O4—S2—C24	108.05 (11)	C18—C17—S1	120.32 (19)
N2—S2—C24	107.47 (9)	C22—C17—S1	119.78 (18)
C6—N2—C7	115.32 (17)	C19—C18—C17	119.3 (2)
C6—N2—S2	119.20 (14)	C19—C18—H18	120.4
C7—N2—S2	115.54 (14)	C17—C18—H18	120.4
C2—C1—C6	119.2 (3)	C18—C19—C20	122.0 (2)
C2—C1—N1	120.0 (2)	C18—C19—H19	119.0
C6—C1—N1	120.8 (2)	C20—C19—H19	119.0
C3—C2—C1	120.5 (3)	C21—C20—C19	117.9 (2)
C3—C2—H2	119.7	C21—C20—C23	120.8 (3)
C1—C2—H2	119.7	C19—C20—C23	121.3 (3)
C2—C3—C4	120.5 (3)	C20—C21—C22	121.6 (2)
C2—C3—H3	119.8	C20—C21—H21	119.2
C4—C3—H3	119.8	C22—C21—H21	119.2
C3—C4—C5	120.1 (3)	C21—C22—C17	119.3 (2)
C3—C4—H4	120.0	C21—C22—H22	120.4
C5—C4—H4	120.0	C17—C22—H22	120.4
C4—C5—C6	120.5 (3)	C20—C23—H23A	109.5
C4—C5—H5	119.8	C20—C23—H23B	109.5
C6—C5—H5	119.8	H23A—C23—H23B	109.5
C5—C6—C1	118.9 (2)	C20—C23—H23C	109.5
C5—C6—N2	119.9 (2)	H23A—C23—H23C	109.5
C1—C6—N2	121.2 (2)	H23B—C23—H23C	109.5
N2—C7—C8	111.01 (18)	C25—C24—C29	120.2 (2)
N2—C7—H7A	109.4	C25—C24—S2	120.27 (18)
C8—C7—H7A	109.4	C29—C24—S2	119.50 (19)
N2—C7—H7B	109.4	C24—C25—C26	119.1 (3)
C8—C7—H7B	109.4	C24—C25—H25	120.5
H7A—C7—H7B	108.0	C26—C25—H25	120.5
C9—C8—N1	118.5 (2)	C27—C26—C25	121.9 (3)
C9—C8—C7	127.6 (2)	C27—C26—H26	119.1
N1—C8—C7	113.88 (18)	C25—C26—H26	119.1
C8—C9—C10	128.7 (2)	C26—C27—C28	117.7 (2)
C8—C9—H9	115.6	C26—C27—C30	121.3 (3)
C10—C9—H9	115.6	C28—C27—C30	121.0 (3)
C11—C10—C15	117.0 (2)	C27—C28—C29	121.6 (3)
C11—C10—C9	124.2 (2)	C27—C28—H28	119.2
C15—C10—C9	118.8 (2)	C29—C28—H28	119.2
C12—C11—C10	121.0 (3)	C24—C29—C28	119.4 (3)
C12—C11—H11	119.5	C24—C29—H29	120.3
C10—C11—H11	119.5	C28—C29—H29	120.3
C11—C12—C13	121.6 (3)	C27—C30—H30A	109.5
C11—C12—H12	119.2	C27—C30—H30B	109.5
C13—C12—H12	119.2	H30A—C30—H30B	109.5
C14—C13—C12	117.6 (3)	C27—C30—H30C	109.5
C14—C13—C16	121.5 (3)	H30A—C30—H30C	109.5
C12—C13—C16	121.0 (3)	H30B—C30—H30C	109.5
N1—C8—C9—C10	174.7 (2)	N1—S1—C17—C18	−86.3 (2)
N2—C7—C8—N1	53.9 (2)	N2—S2—C24—C25	99.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30C···O1^i	0.96	2.78	3.282 (4)	113
C23—H23B···O3^ii	0.96	2.96	3.296 (4)	102
C14—H14···O1^iii	0.93	2.49	3.340 (3)	153
C21—H21···O4^iv	0.93	2.86	3.397 (3)	118
C19—H19···O2^v	0.93	2.52	3.402 (4)	159
C11—H11···O4^iv	0.93	2.58	3.438 (4)	153

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

(III) 2-[(4-methoxyphenyl)methylidene]-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline

Crystal data

C30H28N2O5S2	Dx = 1.383 Mg m^−3
Mr = 560.66	Melting point: 425(1) K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.546 (1) Å	Cell parameters from 57 reflections
b = 11.844 (1) Å	θ = 6.7–38.5°
c = 21.985 (3) Å	µ = 0.24 mm^−1
β = 101.25 (1)°	T = 160 K
V = 2693.3 (5) Å^3	Block, colourless
Z = 4	0.36 × 0.32 × 0.16 mm
F(000) = 1176

Data collection

Siemens P4 diffractometer	3531 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −1→12
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −1→14
Tmin = 0.932, Tmax = 0.962	l = −25→25
6072 measured reflections	3 standard reflections every 97 reflections
4693 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 1.4501P] where P = (Fo^2 + 2Fc^2)/3
4693 reflections	(Δ/σ)max < 0.001
355 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S2	−0.17858 (6)	0.02598 (5)	0.10863 (3)	0.02493 (16)
S1	0.30568 (6)	0.25535 (5)	0.15383 (3)	0.02862 (17)
O1	0.31578 (17)	0.32301 (15)	0.10120 (9)	0.0377 (5)
O2	0.36249 (18)	0.29369 (16)	0.21464 (9)	0.0408 (5)
O3	−0.21816 (17)	−0.03498 (15)	0.15782 (9)	0.0348 (4)
O4	−0.20330 (16)	−0.01990 (15)	0.04704 (8)	0.0326 (4)
O5	−0.25420 (18)	0.32024 (16)	−0.19143 (8)	0.0363 (4)
N1	0.14431 (18)	0.24013 (16)	0.15224 (9)	0.0249 (5)
N2	−0.01757 (18)	0.04089 (16)	0.12811 (9)	0.0231 (4)
C1	0.1100 (2)	0.1757 (2)	0.20220 (11)	0.0258 (5)
C2	0.1488 (2)	0.2125 (2)	0.26324 (12)	0.0332 (6)
H2	0.1927	0.2807	0.2711	0.040*
C3	0.1229 (3)	0.1494 (3)	0.31197 (13)	0.0406 (7)
H3	0.1478	0.1757	0.3524	0.049*
C4	0.0595 (3)	0.0464 (3)	0.30073 (13)	0.0429 (7)
H4	0.0459	0.0019	0.3337	0.052*
C5	0.0167 (2)	0.0104 (2)	0.24054 (12)	0.0331 (6)
H5	−0.0256	−0.0586	0.2332	0.040*
C6	0.0362 (2)	0.0763 (2)	0.19036 (11)	0.0245 (5)
C7	0.0426 (2)	0.09252 (19)	0.07916 (11)	0.0232 (5)
H7A	−0.0144	0.0829	0.0392	0.028*
H7B	0.1233	0.0541	0.0778	0.028*
C8	0.0686 (2)	0.2164 (2)	0.09109 (11)	0.0232 (5)
C9	0.0289 (2)	0.3039 (2)	0.05437 (11)	0.0255 (5)
H9	0.0497	0.3744	0.0721	0.031*
C10	−0.0431 (2)	0.3058 (2)	−0.01015 (11)	0.0237 (5)
C11	−0.1221 (2)	0.3986 (2)	−0.02959 (12)	0.0263 (5)
H11	−0.1265	0.4566	−0.0016	0.032*
C12	−0.1946 (2)	0.4071 (2)	−0.08959 (12)	0.0274 (5)
H12	−0.2464	0.4699	−0.1013	0.033*
C13	−0.1885 (2)	0.3208 (2)	−0.13162 (11)	0.0274 (5)
C14	−0.1085 (2)	0.2274 (2)	−0.11357 (12)	0.0295 (6)
H14	−0.1041	0.1695	−0.1417	0.035*
C15	−0.0363 (2)	0.2211 (2)	−0.05417 (11)	0.0273 (6)
H15	0.0180	0.1595	−0.0430	0.033*
C16	−0.3261 (3)	0.4203 (3)	−0.21311 (13)	0.0487 (8)
H16A	−0.3660	0.4110	−0.2560	0.073*
H16B	−0.2687	0.4839	−0.2088	0.073*
H16C	−0.3916	0.4327	−0.1891	0.073*
C17	0.3652 (2)	0.1192 (2)	0.14378 (11)	0.0248 (5)
C18	0.4030 (2)	0.0912 (2)	0.08884 (12)	0.0304 (6)
H18	0.3954	0.1432	0.0567	0.036*
C19	0.4522 (3)	−0.0156 (2)	0.08263 (12)	0.0324 (6)
H19	0.4796	−0.0342	0.0462	0.039*
C20	0.4618 (2)	−0.0957 (2)	0.12942 (12)	0.0274 (6)
C21	0.4212 (2)	−0.0662 (2)	0.18368 (12)	0.0301 (6)
H21	0.4259	−0.1192	0.2153	0.036*
C22	0.3740 (2)	0.0406 (2)	0.19149 (12)	0.0298 (6)
H22	0.3484	0.0598	0.2283	0.036*
C23	0.5168 (3)	−0.2112 (2)	0.12197 (13)	0.0374 (7)
H23A	0.5635	−0.2371	0.1614	0.056*
H23B	0.5742	−0.2072	0.0931	0.056*
H23C	0.4477	−0.2627	0.1067	0.056*
C24	−0.2454 (2)	0.1627 (2)	0.10561 (11)	0.0239 (5)
C25	−0.2422 (2)	0.2221 (2)	0.16034 (12)	0.0291 (6)
H25	−0.2041	0.1906	0.1983	0.035*
C26	−0.2962 (2)	0.3287 (2)	0.15776 (13)	0.0332 (6)
H26	−0.2943	0.3687	0.1943	0.040*
C27	−0.3536 (2)	0.3773 (2)	0.10133 (13)	0.0302 (6)
C28	−0.3542 (2)	0.3163 (2)	0.04760 (12)	0.0312 (6)
H28	−0.3922	0.3478	0.0097	0.037*
C29	−0.3000 (2)	0.2097 (2)	0.04868 (12)	0.0273 (5)
H29	−0.3002	0.1704	0.0120	0.033*
C30	−0.4141 (3)	0.4933 (2)	0.09864 (15)	0.0453 (8)
H30A	−0.3846	0.5316	0.1373	0.068*
H30B	−0.5065	0.4861	0.0914	0.068*
H30C	−0.3898	0.5358	0.0656	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0197 (3)	0.0190 (3)	0.0336 (3)	0.0001 (2)	−0.0008 (2)	0.0004 (3)
S1	0.0208 (3)	0.0201 (3)	0.0417 (4)	−0.0018 (2)	−0.0019 (3)	−0.0035 (3)
O1	0.0274 (9)	0.0240 (9)	0.0599 (13)	−0.0040 (8)	0.0040 (9)	0.0090 (9)
O2	0.0291 (10)	0.0347 (11)	0.0523 (12)	−0.0033 (9)	−0.0075 (9)	−0.0161 (9)
O3	0.0258 (9)	0.0294 (10)	0.0476 (11)	−0.0024 (8)	0.0033 (8)	0.0127 (9)
O4	0.0268 (9)	0.0260 (9)	0.0408 (11)	−0.0001 (8)	−0.0038 (8)	−0.0109 (8)
O5	0.0394 (10)	0.0382 (11)	0.0283 (10)	0.0095 (9)	−0.0006 (8)	0.0029 (8)
N1	0.0200 (10)	0.0211 (10)	0.0314 (11)	−0.0004 (8)	−0.0010 (8)	−0.0036 (9)
N2	0.0194 (10)	0.0210 (10)	0.0273 (11)	0.0008 (8)	0.0007 (8)	0.0005 (8)
C1	0.0201 (12)	0.0238 (12)	0.0314 (14)	0.0089 (10)	−0.0001 (10)	−0.0042 (11)
C2	0.0275 (13)	0.0336 (14)	0.0347 (15)	0.0119 (11)	−0.0028 (11)	−0.0081 (12)
C3	0.0347 (15)	0.0570 (19)	0.0282 (15)	0.0149 (14)	0.0015 (12)	−0.0062 (14)
C4	0.0360 (15)	0.061 (2)	0.0320 (15)	0.0116 (15)	0.0059 (12)	0.0111 (14)
C5	0.0257 (13)	0.0379 (15)	0.0350 (15)	0.0036 (11)	0.0041 (11)	0.0075 (12)
C6	0.0201 (11)	0.0257 (12)	0.0260 (13)	0.0063 (10)	0.0002 (10)	−0.0012 (10)
C7	0.0228 (12)	0.0190 (12)	0.0262 (13)	0.0003 (10)	0.0007 (10)	−0.0010 (10)
C8	0.0179 (11)	0.0227 (12)	0.0276 (13)	−0.0011 (10)	0.0008 (9)	−0.0029 (10)
C9	0.0220 (12)	0.0183 (12)	0.0352 (14)	−0.0014 (10)	0.0031 (10)	−0.0031 (10)
C10	0.0209 (11)	0.0195 (12)	0.0305 (13)	−0.0017 (10)	0.0045 (10)	0.0040 (10)
C11	0.0272 (12)	0.0191 (12)	0.0329 (14)	−0.0020 (10)	0.0068 (11)	0.0000 (10)
C12	0.0234 (12)	0.0220 (12)	0.0367 (14)	0.0042 (10)	0.0056 (11)	0.0064 (11)
C13	0.0234 (12)	0.0285 (13)	0.0296 (14)	−0.0001 (10)	0.0036 (10)	0.0045 (11)
C14	0.0354 (14)	0.0236 (13)	0.0311 (14)	0.0045 (11)	0.0105 (11)	−0.0003 (11)
C15	0.0280 (13)	0.0222 (12)	0.0321 (14)	0.0065 (10)	0.0070 (11)	0.0050 (11)
C16	0.0510 (19)	0.061 (2)	0.0327 (16)	0.0299 (16)	0.0050 (14)	0.0082 (15)
C17	0.0169 (11)	0.0234 (12)	0.0310 (13)	0.0005 (10)	−0.0026 (10)	−0.0024 (10)
C18	0.0280 (13)	0.0303 (14)	0.0330 (14)	−0.0008 (11)	0.0065 (11)	0.0067 (11)
C19	0.0338 (14)	0.0345 (15)	0.0304 (14)	0.0000 (12)	0.0099 (11)	−0.0018 (12)
C20	0.0181 (11)	0.0264 (13)	0.0355 (14)	0.0003 (10)	−0.0005 (10)	−0.0047 (11)
C21	0.0291 (13)	0.0320 (14)	0.0264 (13)	0.0064 (11)	−0.0014 (11)	0.0048 (11)
C22	0.0270 (13)	0.0348 (14)	0.0260 (13)	0.0082 (11)	0.0014 (10)	0.0012 (11)
C23	0.0336 (14)	0.0317 (15)	0.0452 (17)	0.0048 (12)	0.0029 (12)	−0.0074 (13)
C24	0.0187 (11)	0.0218 (12)	0.0309 (13)	−0.0012 (9)	0.0045 (10)	−0.0006 (10)
C25	0.0263 (12)	0.0334 (14)	0.0278 (13)	0.0012 (11)	0.0051 (10)	0.0027 (11)
C26	0.0311 (14)	0.0322 (14)	0.0376 (15)	0.0005 (12)	0.0098 (12)	−0.0073 (12)
C27	0.0219 (12)	0.0246 (13)	0.0452 (16)	0.0011 (10)	0.0090 (11)	−0.0027 (12)
C28	0.0248 (13)	0.0295 (14)	0.0373 (15)	0.0047 (11)	0.0013 (11)	0.0076 (12)
C29	0.0247 (12)	0.0263 (13)	0.0300 (13)	0.0029 (10)	0.0033 (10)	−0.0001 (11)
C30	0.0379 (16)	0.0303 (15)	0.067 (2)	0.0100 (13)	0.0075 (15)	−0.0043 (14)

Geometric parameters (Å, º)

S2—O3	1.4286 (19)	C13—C14	1.401 (3)
S2—O4	1.4349 (18)	C14—C15	1.380 (3)
S2—N2	1.6776 (19)	C14—H14	0.9300
S2—C24	1.762 (2)	C15—H15	0.9300
S1—O2	1.428 (2)	C16—H16A	0.9600
S1—O1	1.428 (2)	C16—H16B	0.9600
S1—N1	1.705 (2)	C16—H16C	0.9600
S1—C17	1.760 (2)	C17—C18	1.384 (4)
O5—C13	1.361 (3)	C17—C22	1.392 (3)
O5—C16	1.437 (3)	C18—C19	1.384 (4)
N1—C1	1.440 (3)	C18—H18	0.9300
N1—C8	1.451 (3)	C19—C20	1.389 (4)
N2—C6	1.438 (3)	C19—H19	0.9300
N2—C7	1.484 (3)	C20—C21	1.388 (4)
C1—C2	1.394 (3)	C20—C23	1.507 (3)
C1—C6	1.408 (3)	C21—C22	1.382 (4)
C2—C3	1.377 (4)	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.390 (5)	C23—H23A	0.9600
C3—H3	0.9300	C23—H23B	0.9600
C4—C5	1.380 (4)	C23—H23C	0.9600
C4—H4	0.9300	C24—C29	1.388 (3)
C5—C6	1.399 (4)	C24—C25	1.389 (3)
C5—H5	0.9300	C25—C26	1.381 (4)
C7—C8	1.506 (3)	C25—H25	0.9300
C7—H7A	0.9700	C26—C27	1.394 (4)
C7—H7B	0.9700	C26—H26	0.9300
C8—C9	1.330 (3)	C27—C28	1.384 (4)
C9—C10	1.473 (3)	C27—C30	1.511 (4)
C9—H9	0.9300	C28—C29	1.384 (4)
C10—C11	1.395 (3)	C28—H28	0.9300
C10—C15	1.405 (3)	C29—H29	0.9300
C11—C12	1.393 (4)	C30—H30A	0.9600
C11—H11	0.9300	C30—H30B	0.9600
C12—C13	1.387 (4)	C30—H30C	0.9600
C12—H12	0.9300
O3—S2—O4	119.79 (11)	C15—C14—C13	120.1 (2)
O3—S2—N2	106.89 (10)	C15—C14—H14	120.0
O4—S2—N2	105.62 (10)	C13—C14—H14	120.0
O3—S2—C24	108.63 (11)	C14—C15—C10	121.4 (2)
O4—S2—C24	108.35 (11)	C14—C15—H15	119.3
N2—S2—C24	106.85 (10)	C10—C15—H15	119.3
O2—S1—O1	119.72 (12)	O5—C16—H16A	109.5
O2—S1—N1	106.71 (11)	O5—C16—H16B	109.5
O1—S1—N1	105.94 (11)	H16A—C16—H16B	109.5
O2—S1—C17	108.30 (11)	O5—C16—H16C	109.5
O1—S1—C17	109.11 (12)	H16A—C16—H16C	109.5
N1—S1—C17	106.25 (11)	H16B—C16—H16C	109.5
C13—O5—C16	116.9 (2)	C18—C17—C22	120.6 (2)
C1—N1—C8	115.44 (19)	C18—C17—S1	119.98 (19)
C1—N1—S1	116.01 (15)	C22—C17—S1	119.42 (19)
C8—N1—S1	113.98 (16)	C19—C18—C17	118.8 (2)
C6—N2—C7	115.16 (19)	C19—C18—H18	120.6
C6—N2—S2	117.73 (16)	C17—C18—H18	120.6
C7—N2—S2	114.41 (15)	C18—C19—C20	121.7 (2)
C2—C1—C6	119.2 (2)	C18—C19—H19	119.1
C2—C1—N1	119.9 (2)	C20—C19—H19	119.1
C6—C1—N1	120.9 (2)	C21—C20—C19	118.3 (2)
C3—C2—C1	120.9 (3)	C21—C20—C23	120.8 (2)
C3—C2—H2	119.5	C19—C20—C23	120.9 (2)
C1—C2—H2	119.5	C22—C21—C20	121.0 (2)
C2—C3—C4	120.0 (3)	C22—C21—H21	119.5
C2—C3—H3	120.0	C20—C21—H21	119.5
C4—C3—H3	120.0	C21—C22—C17	119.4 (2)
C5—C4—C3	119.9 (3)	C21—C22—H22	120.3
C5—C4—H4	120.1	C17—C22—H22	120.3
C3—C4—H4	120.1	C20—C23—H23A	109.5
C4—C5—C6	120.9 (3)	C20—C23—H23B	109.5
C4—C5—H5	119.6	H23A—C23—H23B	109.5
C6—C5—H5	119.6	C20—C23—H23C	109.5
C5—C6—C1	118.8 (2)	H23A—C23—H23C	109.5
C5—C6—N2	119.8 (2)	H23B—C23—H23C	109.5
C1—C6—N2	121.4 (2)	C29—C24—C25	120.9 (2)
N2—C7—C8	111.34 (19)	C29—C24—S2	119.66 (19)
N2—C7—H7A	109.4	C25—C24—S2	119.40 (19)
C8—C7—H7A	109.4	C26—C25—C24	119.2 (2)
N2—C7—H7B	109.4	C26—C25—H25	120.4
C8—C7—H7B	109.4	C24—C25—H25	120.4
H7A—C7—H7B	108.0	C25—C26—C27	121.2 (2)
C9—C8—N1	117.6 (2)	C25—C26—H26	119.4
C9—C8—C7	128.9 (2)	C27—C26—H26	119.4
N1—C8—C7	113.5 (2)	C28—C27—C26	118.2 (2)
C8—C9—C10	129.7 (2)	C28—C27—C30	120.7 (3)
C8—C9—H9	115.2	C26—C27—C30	121.1 (2)
C10—C9—H9	115.2	C27—C28—C29	121.9 (2)
C11—C10—C15	117.3 (2)	C27—C28—H28	119.0
C11—C10—C9	118.2 (2)	C29—C28—H28	119.0
C15—C10—C9	124.5 (2)	C28—C29—C24	118.6 (2)
C12—C11—C10	122.1 (2)	C28—C29—H29	120.7
C12—C11—H11	118.9	C24—C29—H29	120.7
C10—C11—H11	118.9	C27—C30—H30A	109.5
C13—C12—C11	119.3 (2)	C27—C30—H30B	109.5
C13—C12—H12	120.4	H30A—C30—H30B	109.5
C11—C12—H12	120.4	C27—C30—H30C	109.5
O5—C13—C12	124.5 (2)	H30A—C30—H30C	109.5
O5—C13—C14	115.7 (2)	H30B—C30—H30C	109.5
C12—C13—C14	119.8 (2)
N1—C8—C9—C10	176.8 (2)	N1—S1—C17—C18	109.2 (2)
N2—C7—C8—N1	54.1 (3)	N2—S2—C24—C25	−71.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O2^i	0.93	2.66	3.311 (3)	128
C25—H25···O5^ii	0.93	2.58	3.324 (3)	137
C16—H16B···O2^iii	0.96	2.81	3.409 (4)	122
C12—H12···O1^iii	0.93	2.56	3.434 (3)	157
C15—H15···O4^iv	0.93	2.57	3.454 (3)	158

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

(IV) 2-[(4-chlorophenyl)methylidene]-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline

Crystal data

C29H25ClN2O4S2	Dx = 1.399 Mg m^−3
Mr = 565.08	Melting point: 418(1) K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5361 (10) Å	Cell parameters from 34 reflections
b = 24.040 (3) Å	θ = 3.4–12.5°
c = 10.6146 (10) Å	µ = 0.34 mm^−1
β = 93.863 (10)°	T = 293 K
V = 2682.4 (5) Å^3	Needle, colourless
Z = 4	0.56 × 0.32 × 0.28 mm
F(000) = 1176

Data collection

Siemens P4 diffractometer	2437 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −1→12
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −28→1
Tmin = 0.866, Tmax = 0.910	l = −12→12
5563 measured reflections	3 standard reflections every 97 reflections
4509 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0318P)^2] where P = (Fo^2 + 2Fc^2)/3
4509 reflections	(Δ/σ)max = 0.007
345 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.79678 (8)	0.80715 (4)	0.70774 (8)	0.0515 (3)
S2	1.25270 (9)	0.88794 (4)	0.49271 (9)	0.0551 (3)
Cl	1.29786 (10)	1.03411 (5)	1.06057 (10)	0.0794 (3)
N1	0.9534 (2)	0.81839 (10)	0.6901 (2)	0.0405 (7)
N2	1.1048 (2)	0.86253 (11)	0.4948 (2)	0.0442 (7)
O1	0.7743 (2)	0.74912 (10)	0.6882 (2)	0.0666 (7)
O2	0.7714 (2)	0.83227 (12)	0.8241 (2)	0.0692 (8)
O3	1.3113 (2)	0.85966 (12)	0.3922 (2)	0.0740 (8)
O4	1.2390 (2)	0.94674 (10)	0.4888 (2)	0.0696 (7)
C1	1.0208 (3)	0.78266 (14)	0.6095 (3)	0.0410 (8)
C2	1.0228 (3)	0.72568 (15)	0.6330 (3)	0.0537 (9)
H2	0.9791	0.7115	0.6992	0.064*
C3	1.0887 (4)	0.68992 (16)	0.5595 (4)	0.0635 (10)
H3	1.0923	0.6521	0.5783	0.076*
C4	1.1493 (4)	0.71043 (17)	0.4582 (4)	0.0637 (11)
H4	1.1891	0.6861	0.4053	0.076*
C5	1.1511 (3)	0.76653 (17)	0.4350 (3)	0.0579 (10)
H5	1.1927	0.7799	0.3666	0.069*
C6	1.0913 (3)	0.80387 (14)	0.5125 (3)	0.0402 (8)
C7	1.0123 (3)	0.89753 (13)	0.5596 (3)	0.0454 (8)
H7A	0.9321	0.8983	0.5092	0.054*
H7B	1.0442	0.9353	0.5662	0.054*
C8	0.9901 (3)	0.87636 (13)	0.6887 (3)	0.0383 (8)
C9	1.0014 (3)	0.90398 (13)	0.7972 (3)	0.0435 (8)
H9	0.9824	0.8839	0.8684	0.052*
C10	1.0403 (3)	0.96234 (13)	0.8197 (3)	0.0418 (8)
C11	0.9944 (3)	1.00757 (14)	0.7489 (3)	0.0524 (9)
H11	0.9330	1.0022	0.6829	0.063*
C12	1.0395 (4)	1.06075 (15)	0.7761 (3)	0.0599 (10)
H12	1.0065	1.0908	0.7293	0.072*
C13	1.1327 (4)	1.06966 (16)	0.8715 (3)	0.0579 (10)
H13	1.1643	1.1052	0.8882	0.069*
C14	1.1778 (3)	1.02504 (15)	0.9414 (3)	0.0489 (9)
C15	1.1309 (3)	0.97212 (14)	0.9175 (3)	0.0445 (8)
H15	1.1607	0.9427	0.9680	0.053*
C16	0.7182 (3)	0.84430 (14)	0.5840 (3)	0.0459 (8)
C17	0.7080 (3)	0.82139 (14)	0.4634 (3)	0.0513 (9)
H17	0.7385	0.7858	0.4491	0.062*
C18	0.6519 (3)	0.85249 (15)	0.3650 (3)	0.0549 (10)
H18	0.6446	0.8373	0.2842	0.066*
C19	0.6063 (3)	0.90553 (15)	0.3838 (3)	0.0520 (9)
C20	0.6196 (3)	0.92772 (14)	0.5035 (4)	0.0565 (10)
H20	0.5899	0.9635	0.5172	0.068*
C21	0.6763 (3)	0.89795 (15)	0.6041 (3)	0.0547 (10)
H21	0.6861	0.9138	0.6841	0.066*
C22	0.5420 (4)	0.93897 (16)	0.2771 (4)	0.0731 (12)
H22A	0.4990	0.9142	0.2174	0.110*
H22B	0.6047	0.9600	0.2359	0.110*
H22C	0.4814	0.9639	0.3103	0.110*
C23	1.3329 (3)	0.86890 (14)	0.6368 (3)	0.0460 (8)
C24	1.3838 (3)	0.81639 (16)	0.6513 (4)	0.0619 (10)
H24	1.3782	0.7912	0.5847	0.074*
C25	1.4437 (3)	0.80171 (16)	0.7672 (4)	0.0602 (10)
H25	1.4773	0.7661	0.7780	0.072*
C26	1.4545 (3)	0.83865 (17)	0.8667 (3)	0.0554 (10)
C27	1.4046 (3)	0.89139 (16)	0.8488 (4)	0.0588 (10)
H27	1.4125	0.9171	0.9143	0.071*
C28	1.3429 (3)	0.90640 (15)	0.7349 (4)	0.0559 (10)
H28	1.3083	0.9418	0.7245	0.067*
C29	1.5181 (4)	0.82181 (19)	0.9927 (4)	0.0798 (13)
H29A	1.5429	0.7834	0.9896	0.120*
H29B	1.4598	0.8268	1.0574	0.120*
H29C	1.5921	0.8445	1.0110	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0455 (5)	0.0625 (6)	0.0474 (5)	−0.0109 (5)	0.0101 (4)	0.0032 (5)
S2	0.0421 (5)	0.0667 (7)	0.0570 (6)	−0.0143 (5)	0.0076 (4)	0.0087 (5)
Cl	0.0668 (7)	0.0947 (8)	0.0752 (7)	−0.0125 (6)	−0.0062 (6)	−0.0280 (6)
N1	0.0375 (15)	0.0463 (17)	0.0381 (15)	−0.0098 (13)	0.0044 (12)	0.0005 (13)
N2	0.0357 (15)	0.0551 (18)	0.0419 (15)	−0.0071 (14)	0.0036 (13)	0.0017 (13)
O1	0.0583 (16)	0.0590 (17)	0.0830 (19)	−0.0222 (13)	0.0078 (14)	0.0115 (14)
O2	0.0546 (16)	0.106 (2)	0.0491 (15)	−0.0106 (15)	0.0192 (12)	−0.0031 (14)
O3	0.0542 (16)	0.108 (2)	0.0628 (16)	−0.0198 (16)	0.0260 (14)	−0.0100 (15)
O4	0.0586 (16)	0.0628 (17)	0.0872 (19)	−0.0151 (14)	0.0031 (14)	0.0250 (15)
C1	0.0385 (19)	0.048 (2)	0.0354 (17)	−0.0041 (16)	−0.0018 (15)	−0.0047 (16)
C2	0.052 (2)	0.051 (2)	0.058 (2)	−0.0125 (19)	0.0013 (18)	−0.0060 (19)
C3	0.063 (3)	0.052 (2)	0.075 (3)	−0.006 (2)	0.001 (2)	−0.017 (2)
C4	0.048 (2)	0.071 (3)	0.074 (3)	0.000 (2)	0.013 (2)	−0.025 (2)
C5	0.043 (2)	0.076 (3)	0.055 (2)	−0.006 (2)	0.0061 (18)	−0.015 (2)
C6	0.0316 (17)	0.051 (2)	0.0375 (18)	−0.0038 (16)	−0.0013 (14)	−0.0061 (16)
C7	0.0392 (19)	0.052 (2)	0.0444 (19)	−0.0016 (17)	−0.0029 (16)	0.0093 (16)
C8	0.0338 (17)	0.042 (2)	0.0393 (18)	0.0002 (16)	−0.0004 (14)	0.0056 (16)
C9	0.040 (2)	0.047 (2)	0.0434 (19)	−0.0013 (16)	0.0008 (16)	0.0046 (16)
C10	0.048 (2)	0.044 (2)	0.0340 (17)	0.0024 (17)	0.0072 (16)	−0.0008 (16)
C11	0.061 (2)	0.052 (2)	0.044 (2)	0.008 (2)	0.0012 (18)	0.0019 (18)
C12	0.080 (3)	0.049 (2)	0.052 (2)	0.015 (2)	0.014 (2)	0.0062 (19)
C13	0.064 (3)	0.051 (2)	0.060 (2)	−0.001 (2)	0.016 (2)	−0.007 (2)
C14	0.044 (2)	0.059 (2)	0.0440 (19)	−0.0060 (19)	0.0061 (17)	−0.0101 (19)
C15	0.045 (2)	0.049 (2)	0.0396 (19)	0.0063 (18)	0.0057 (17)	0.0029 (16)
C16	0.0325 (19)	0.052 (2)	0.054 (2)	−0.0078 (17)	0.0070 (16)	−0.0013 (18)
C17	0.051 (2)	0.047 (2)	0.056 (2)	−0.0034 (18)	0.0025 (18)	−0.0090 (18)
C18	0.053 (2)	0.059 (2)	0.053 (2)	−0.005 (2)	0.0027 (19)	−0.0080 (19)
C19	0.043 (2)	0.050 (2)	0.064 (2)	−0.0056 (18)	0.0094 (18)	−0.0012 (19)
C20	0.052 (2)	0.037 (2)	0.082 (3)	0.0044 (18)	0.016 (2)	−0.013 (2)
C21	0.046 (2)	0.061 (3)	0.057 (2)	−0.0043 (19)	0.0088 (18)	−0.014 (2)
C22	0.070 (3)	0.069 (3)	0.082 (3)	0.003 (2)	0.011 (2)	0.017 (2)
C23	0.0331 (18)	0.049 (2)	0.057 (2)	−0.0104 (17)	0.0064 (16)	−0.0045 (18)
C24	0.046 (2)	0.057 (3)	0.082 (3)	−0.003 (2)	−0.004 (2)	−0.019 (2)
C25	0.043 (2)	0.058 (2)	0.079 (3)	0.0032 (19)	−0.002 (2)	−0.006 (2)
C26	0.035 (2)	0.067 (3)	0.065 (3)	−0.0043 (19)	0.0102 (19)	0.007 (2)
C27	0.045 (2)	0.065 (3)	0.067 (3)	−0.005 (2)	0.002 (2)	−0.013 (2)
C28	0.038 (2)	0.053 (2)	0.076 (3)	−0.0013 (18)	0.0016 (19)	−0.004 (2)
C29	0.065 (3)	0.099 (3)	0.074 (3)	0.003 (3)	−0.001 (2)	0.010 (3)

Geometric parameters (Å, º)

S1—O2	1.417 (2)	C12—H12	0.9300
S1—O1	1.428 (3)	C13—C14	1.371 (5)
S1—N1	1.695 (3)	C13—H13	0.9300
S1—C16	1.750 (3)	C14—C15	1.382 (5)
S2—O4	1.421 (3)	C15—H15	0.9300
S2—O3	1.439 (3)	C16—C21	1.384 (5)
S2—N2	1.675 (3)	C16—C17	1.391 (4)
S2—C23	1.758 (3)	C17—C18	1.385 (5)
Cl—C14	1.741 (3)	C17—H17	0.9300
N1—C1	1.434 (4)	C18—C19	1.382 (5)
N1—C8	1.447 (4)	C18—H18	0.9300
N2—C6	1.431 (4)	C19—C20	1.376 (5)
N2—C7	1.491 (4)	C19—C22	1.511 (5)
C1—C2	1.392 (5)	C20—C21	1.387 (5)
C1—C6	1.405 (4)	C20—H20	0.9300
C2—C3	1.380 (5)	C21—H21	0.9300
C2—H2	0.9300	C22—H22A	0.9600
C3—C4	1.378 (5)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600
C4—C5	1.371 (5)	C23—C28	1.376 (5)
C4—H4	0.9300	C23—C24	1.376 (5)
C5—C6	1.396 (4)	C24—C25	1.390 (5)
C5—H5	0.9300	C24—H24	0.9300
C7—C8	1.494 (4)	C25—C26	1.378 (5)
C7—H7A	0.9700	C25—H25	0.9300
C7—H7B	0.9700	C26—C27	1.381 (5)
C8—C9	1.328 (4)	C26—C29	1.510 (5)
C9—C10	1.476 (4)	C27—C28	1.382 (5)
C9—H9	0.9300	C27—H27	0.9300
C10—C15	1.383 (4)	C28—H28	0.9300
C10—C11	1.390 (4)	C29—H29A	0.9600
C11—C12	1.387 (5)	C29—H29B	0.9600
C11—H11	0.9300	C29—H29C	0.9600
C12—C13	1.380 (5)
O2—S1—O1	120.27 (17)	C14—C13—C12	118.7 (3)
O2—S1—N1	105.71 (14)	C14—C13—H13	120.7
O1—S1—N1	107.04 (15)	C12—C13—H13	120.7
O2—S1—C16	109.24 (17)	C13—C14—C15	121.0 (3)
O1—S1—C16	108.90 (16)	C13—C14—Cl	120.2 (3)
N1—S1—C16	104.51 (14)	C15—C14—Cl	118.8 (3)
O4—S2—O3	119.72 (17)	C14—C15—C10	121.0 (3)
O4—S2—N2	105.69 (15)	C14—C15—H15	119.5
O3—S2—N2	106.46 (15)	C10—C15—H15	119.5
O4—S2—C23	109.06 (17)	C21—C16—C17	120.3 (3)
O3—S2—C23	108.51 (17)	C21—C16—S1	120.0 (3)
N2—S2—C23	106.65 (14)	C17—C16—S1	119.5 (3)
C1—N1—C8	115.3 (2)	C18—C17—C16	118.9 (3)
C1—N1—S1	119.7 (2)	C18—C17—H17	120.6
C8—N1—S1	114.7 (2)	C16—C17—H17	120.6
C6—N2—C7	114.9 (2)	C19—C18—C17	121.6 (3)
C6—N2—S2	117.5 (2)	C19—C18—H18	119.2
C7—N2—S2	116.0 (2)	C17—C18—H18	119.2
C2—C1—C6	119.1 (3)	C20—C19—C18	118.5 (3)
C2—C1—N1	119.0 (3)	C20—C19—C22	119.9 (3)
C6—C1—N1	121.8 (3)	C18—C19—C22	121.7 (3)
C3—C2—C1	120.9 (3)	C19—C20—C21	121.5 (3)
C3—C2—H2	119.6	C19—C20—H20	119.2
C1—C2—H2	119.6	C21—C20—H20	119.2
C4—C3—C2	119.7 (4)	C16—C21—C20	119.2 (3)
C4—C3—H3	120.1	C16—C21—H21	120.4
C2—C3—H3	120.1	C20—C21—H21	120.4
C5—C4—C3	120.3 (4)	C19—C22—H22A	109.5
C5—C4—H4	119.8	C19—C22—H22B	109.5
C3—C4—H4	119.8	H22A—C22—H22B	109.5
C4—C5—C6	120.9 (4)	C19—C22—H22C	109.5
C4—C5—H5	119.5	H22A—C22—H22C	109.5
C6—C5—H5	119.5	H22B—C22—H22C	109.5
C5—C6—C1	118.7 (3)	C28—C23—C24	120.5 (3)
C5—C6—N2	120.2 (3)	C28—C23—S2	119.7 (3)
C1—C6—N2	121.1 (3)	C24—C23—S2	119.8 (3)
N2—C7—C8	112.2 (2)	C23—C24—C25	118.8 (4)
N2—C7—H7A	109.2	C23—C24—H24	120.6
C8—C7—H7A	109.2	C25—C24—H24	120.6
N2—C7—H7B	109.2	C26—C25—C24	121.6 (4)
C8—C7—H7B	109.2	C26—C25—H25	119.2
H7A—C7—H7B	107.9	C24—C25—H25	119.2
C9—C8—N1	118.8 (3)	C25—C26—C27	118.4 (3)
C9—C8—C7	127.9 (3)	C25—C26—C29	121.0 (4)
N1—C8—C7	113.3 (3)	C27—C26—C29	120.6 (4)
C8—C9—C10	128.5 (3)	C26—C27—C28	120.8 (4)
C8—C9—H9	115.7	C26—C27—H27	119.6
C10—C9—H9	115.7	C28—C27—H27	119.6
C15—C10—C11	118.1 (3)	C23—C28—C27	119.9 (3)
C15—C10—C9	116.9 (3)	C23—C28—H28	120.0
C11—C10—C9	125.0 (3)	C27—C28—H28	120.0
C12—C11—C10	120.4 (3)	C26—C29—H29A	109.5
C12—C11—H11	119.8	C26—C29—H29B	109.5
C10—C11—H11	119.8	H29A—C29—H29B	109.5
C13—C12—C11	120.8 (3)	C26—C29—H29C	109.5
C13—C12—H12	119.6	H29A—C29—H29C	109.5
C11—C12—H12	119.6	H29B—C29—H29C	109.5
N1—C8—C9—C10	178.4 (3)	N1—S1—C16—C17	80.0 (3)
N2—C7—C8—N1	−53.5 (3)	N2—S2—C23—C24	81.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29C···O2^i	0.96	2.85	3.321 (5)	112
C20—H20···O4^ii	0.93	2.82	3.364 (4)	119
C18—H18···O1^iii	0.93	2.72	3.388 (4)	129
C17—H17···O1^iii	0.93	2.94	3.488 (4)	119

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