Racemic 9,10-dimeth­oxy-3-methyl-6-phenyl-7,7a-dihydro­benzo[b]benzo[4,5]isothia­zolo[2,3-d][1,4]diazepine 12,12-dioxide

Bassin, J.P.; Shah, V.P.; Martin, L.; Horton, P.N.

doi:10.1107/S1600536811004983

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o684-o685

doi:10.1107/S1600536811004983

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Racemic 9,10-dimethoxy-3-methyl-6-phenyl-7,7a-dihydrobenzo[b]benzo[4,5]isothiazolo[2,3-d][1,4]diazepine 12,12-dioxide

Jatinder P. Bassin,^a ^* Virender P. Shah,^a Lee Martin ^a and Peter N. Horton ^b

^aSchool of Pharmacy, University of Hertfordshire, College Lane, Hatfield AL10 9AB, England, and ^bSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England
^*Correspondence e-mail: j.p.bassin@herts.ac.uk

(Received 13 December 2010; accepted 9 February 2011; online 23 February 2011)

There are two molecules in the asymmetric unit of the title compound, C₂₄H₂₂N₂O₄S. The conformation of the seven-membered ring is twisted boat for both molecules. The molecule is chiral, but crystal symmetry generates a recemate. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Zia-ul-Haq et al. (2007 ); Boudina et al. (2007 ); Doubia et al. (2007 ); Sanudo et al. (2009 ); Spencer et al. (2009 ); Swamy et al. (2008 ). For the psychotropic properties of aptazapine [systematic name: 2-methyl-1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine] and bretazenil [systematic name: t-butyl-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate], see: Silvestri et al. (1994 ); Landquist (1984 ); Insuasty et al. (2008 ); Bennamane et al. (2008 ); Schutz (1982 ). For the bioactivity of benzodiazepines, see: Constanzo et al. (1990 ); Kelly et al. (1997 ). For the effect on the bioactivity of fusing different heterocyclic rings to the 1,4- and 1,5-benzodiazepine system, see: Chimirri et al. (1993a ,b ). For the synthesis of the title compound, see: Bassin et al. (2000 ).

Experimental

Crystal data

C₂₄H₂₂N₂O₄S
M_r = 434.51
Triclinic, $[P \overline 1]$
a = 11.9007 (4) Å
b = 12.8521 (4) Å
c = 14.6202 (5) Å
α = 109.852 (2)°
β = 90.743 (2)°
γ = 92.775 (2)°
V = 2099.76 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 120 K
0.50 × 0.30 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.912, T_max = 0.981
31054 measured reflections
7393 independent reflections
5463 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.01
7393 reflections
566 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.89	2.44	3.303 (3)	162
N1—H1B⋯Cl1ⁱ	0.89	2.36	3.236 (2)	170
N1—H1C⋯O1ⁱⁱ	0.89	2.05	2.901 (4)	159
O1—H1H⋯Cl1	0.85	2.45	3.290 (3)	170
O1—H1I⋯Cl1ⁱⁱⁱ	0.85	2.39	3.228 (2)	170
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) x-1, y, z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: DENZO, COLLECT and maXus (Mackay et al., 1999 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin, et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004983/rk2256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004983/rk2256Isup2.hkl

checkCIF report

Comment top

In recent years tetracyclic benzodiazepines have received a great deal of attention due to the psychotropic properties of such compounds as aptazapine and bretazenil (Silvestri et al., 1994; Landquist, 1984; Insuasty et al., 2008; Bennamane et al., 2008; Schutz, 1982). A number of structures of benzodiazepines have been reported: Zia-ul-Haq et al., (2007); Boudina et al., (2007); Doubia et al., (2007); Sanudo et al., (2009); Spencer et al., (2009); Swamy et al., (2008). Benzodiazepines containing heterocycles fused to the seven-membered ring have shown important and varied bioactivities (Constanzo et al., 1990; Kelly et al., 1997). It has been demonstrated that by fusing different heterocyclic rings to the 1,4- and 1,5-benzodiazepine system enhances the biological activity of these compounds (Chimirri et al., 1993a,b). We previously reported the synthesis of a new heterocyclic ring system dihydrobenzo[b]benzo[4,5]isothiazolo[2,3-d][1,4]diazepine 12,12-dioxide (Bassin et al., 2000). As, an extension of this work we report the crystal structure of the enantiomeric mixture of 9,10-dimethoxy-3-methyl-6-phenyl-7,7a-dihydrobenzo[b] benzo[4,5]isothiazolo [2,3-d][1,4]diazepine 12,12-dioxide.

Related literature top

For related structures, see: Zia-ul-Haq et al. (2007); Boudina et al. (2007); Doubia et al. (2007); Sanudo et al. (2009); Spencer et al. (2009); Swamy et al. (2008). For the psychotropic properties of aptazapine [2-methyl-1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine] and bretazenil [t-butyl-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo(1,5-a)pyrrolo(2,1-c)(1,4)benzodiazepine-1-carboxylate], see: Silvestri et al. (1994); Landquist (1984); Insuasty et al. (2008); Bennamane et al. (2008); Schutz (1982). For the bioactivity of benzodiazepines, see: Constanzo et al. (1990); Kelly et al. (1997). For the effect on the bioactivity of fusing different heterocyclic rings to the 1,4- and 1,5-benzodiazepine system, see: Chimirri et al. (1993a,b). For the synthesis of the title compound, see: Bassin et al. (2000).

Experimental top

The title compound was synthesised following a modified procedure (Bassin et al., 2000) by refluxing (E)-4,5-dimethoxy-2-(3-oxo-3-phenylprop-1-en-1-yl)benzene-1-sulfonyl chloride with 3,4-diaminotoluene in ethanol for 1 hour. The reaction mixture was allowed to cool to room temperature the resulting precipitated product was filtered under suction and thoroughly washed with aqueous ethanol. The air dried product was re-crystallised from ethanol. A yellow crystalline product (yield: 82%, m.p.: 498 K) was obtained.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997), COLLECT (Hooft, 1998) and maXus (Mackay et al., 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin, et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

9,10-dimethoxy-3-methyl-6-phenyl-7,7a- dihydrobenzo[b]benzo[4,5]isothiazolo[2,3-d][1,4]diazepine 12,12-dioxide top

Crystal data top

C₂₄H₂₂N₂O₄S	Z = 4
M_r = 434.51	F(000) = 912
Triclinic, P1	D_x = 1.375 Mg m⁻³
Hall symbol: -P 1	Melting point: 498 K
a = 11.9007 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.8521 (4) Å	Cell parameters from 25443 reflections
c = 14.6202 (5) Å	θ = 2.9–27.5°
α = 109.852 (2)°	µ = 0.19 mm⁻¹
β = 90.743 (2)°	T = 120 K
γ = 92.775 (2)°	Prism, yellow
V = 2099.76 (12) Å³	0.50 × 0.30 × 0.10 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	7393 independent reflections
Radiation source: fine-focus sealed tube	5463 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ϕ– and ω scans	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	k = −15→15
T_min = 0.912, T_max = 0.981	l = −17→17
31054 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0595P)² + 0.1891P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
7393 reflections	Δρ_max = 0.29 e Å⁻³
566 parameters	Δρ_min = −0.46 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0053 (7)

Crystal data top

C₂₄H₂₂N₂O₄S	γ = 92.775 (2)°
M_r = 434.51	V = 2099.76 (12) Å³
Triclinic, P1	Z = 4
a = 11.9007 (4) Å	Mo Kα radiation
b = 12.8521 (4) Å	µ = 0.19 mm⁻¹
c = 14.6202 (5) Å	T = 120 K
α = 109.852 (2)°	0.50 × 0.30 × 0.10 mm
β = 90.743 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	7393 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	5463 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.981	R_int = 0.060
31054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
7393 reflections	Δρ_min = −0.46 e Å⁻³
566 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.3992 (2)	−0.2363 (2)	0.14280 (18)	0.0360 (6)
H1A	0.4094	−0.1782	0.2067	0.054*
H1B	0.4607	−0.2867	0.1329	0.054*
H1C	0.3272	−0.2778	0.1396	0.054*
C2	0.42922 (19)	−0.05068 (19)	−0.13723 (16)	0.0311 (5)
H2A	0.3605	−0.0683	−0.1784	0.047*
H2B	0.4933	−0.0824	−0.1766	0.047*
H2C	0.4423	0.0299	−0.1089	0.047*
C3	0.16980 (16)	0.00163 (15)	0.14164 (14)	0.0188 (4)
C4	0.24041 (17)	−0.08172 (16)	0.14182 (14)	0.0217 (5)
H4	0.2314	−0.1188	0.1877	0.026*
C5	0.32354 (17)	−0.10949 (16)	0.07437 (15)	0.0225 (5)
C6	0.33481 (17)	−0.05692 (16)	0.00370 (14)	0.0215 (5)
C7	0.26602 (17)	0.02657 (16)	0.00462 (14)	0.0222 (5)
H7	0.2738	0.0637	−0.0413	0.027*
C8	0.18439 (16)	0.05466 (15)	0.07553 (14)	0.0197 (4)
C9	0.07022 (16)	0.03569 (16)	0.20530 (14)	0.0195 (4)
H9	0.0141	−0.0289	0.1893	0.023*
C10	0.09793 (17)	0.07586 (16)	0.31449 (14)	0.0211 (4)
H10A	0.0271	0.0850	0.3505	0.025*
H10B	0.1404	0.0195	0.3303	0.025*
C11	0.16693 (16)	0.18492 (16)	0.34651 (13)	0.0194 (4)
C12	0.29050 (17)	0.18973 (16)	0.36576 (14)	0.0210 (5)
C13	0.34603 (18)	0.10086 (17)	0.37451 (15)	0.0265 (5)
H13	0.3046	0.0338	0.3690	0.032*
C14	0.46215 (18)	0.10953 (19)	0.39138 (16)	0.0306 (5)
H14	0.4992	0.0483	0.3976	0.037*
C15	0.52371 (18)	0.20556 (19)	0.39914 (15)	0.0317 (5)
H15	0.6030	0.2107	0.4100	0.038*
C16	0.46915 (18)	0.2947 (2)	0.39095 (17)	0.0334 (6)
H16	0.5111	0.3614	0.3962	0.040*
C17	0.35396 (17)	0.28733 (18)	0.37510 (15)	0.0272 (5)
H17	0.3173	0.3495	0.3705	0.033*
C18	−0.04226 (16)	0.20694 (16)	0.24328 (14)	0.0207 (5)
C19	−0.15279 (17)	0.21991 (17)	0.22056 (15)	0.0250 (5)
H19	−0.1860	0.1735	0.1601	0.030*
C20	−0.21585 (17)	0.29909 (17)	0.28400 (15)	0.0259 (5)
H20	−0.2914	0.3066	0.2665	0.031*
C21	−0.16983 (17)	0.36800 (16)	0.37326 (15)	0.0235 (5)
C22	−0.05783 (17)	0.35632 (16)	0.39450 (15)	0.0235 (5)
H22	−0.0245	0.4042	0.4543	0.028*
C23	0.00699 (17)	0.27780 (16)	0.33205 (15)	0.0213 (5)
C24	−0.23848 (18)	0.45185 (18)	0.44470 (16)	0.0308 (5)
H24A	−0.2971	0.4754	0.4095	0.046*
H24B	−0.1895	0.5162	0.4820	0.046*
H24C	−0.2737	0.4185	0.4892	0.046*
N1	0.02092 (13)	0.12406 (13)	0.17640 (11)	0.0204 (4)
N2	0.12208 (13)	0.27710 (13)	0.35685 (12)	0.0219 (4)
O1	0.40000 (12)	−0.18679 (11)	0.06850 (10)	0.0290 (4)
O2	0.41702 (12)	−0.09601 (12)	−0.06133 (10)	0.0282 (3)
O3	0.13467 (12)	0.26485 (11)	0.12453 (10)	0.0278 (4)
O4	0.01497 (12)	0.12890 (11)	0.00291 (10)	0.0265 (3)
S1	0.08537 (4)	0.15358 (4)	0.08842 (4)	0.02013 (14)
C25	0.4183 (2)	0.30217 (18)	0.13538 (18)	0.0388 (6)
H25A	0.3708	0.2635	0.1693	0.058*
H25B	0.4746	0.2526	0.0987	0.058*
H25C	0.3714	0.3246	0.0905	0.058*
C26	0.64950 (18)	0.67805 (19)	0.35264 (17)	0.0348 (6)
H26A	0.6307	0.7317	0.3214	0.052*
H26B	0.7296	0.6639	0.3453	0.052*
H26C	0.6332	0.7079	0.4220	0.052*
C27	0.23523 (16)	0.57054 (16)	0.29537 (14)	0.0188 (4)
C28	0.29256 (17)	0.47623 (16)	0.24852 (14)	0.0218 (5)
H28	0.2523	0.4079	0.2147	0.026*
C29	0.40916 (17)	0.48312 (16)	0.25179 (14)	0.0233 (5)
C30	0.46967 (16)	0.58300 (16)	0.30635 (14)	0.0215 (5)
C31	0.41321 (17)	0.67598 (16)	0.35242 (14)	0.0210 (5)
H31	0.4527	0.7439	0.3885	0.025*
C32	0.29588 (16)	0.66768 (16)	0.34460 (14)	0.0192 (4)
C33	0.10869 (17)	0.57821 (16)	0.30258 (14)	0.0205 (4)
H33	0.0811	0.5345	0.3437	0.025*
C34	0.04001 (16)	0.53834 (16)	0.20675 (14)	0.0201 (4)
H34A	0.0568	0.4608	0.1700	0.024*
H34B	−0.0411	0.5395	0.2210	0.024*
C35	0.06480 (17)	0.60900 (16)	0.14439 (14)	0.0213 (5)
C36	0.13310 (17)	0.56838 (16)	0.05648 (14)	0.0224 (5)
C37	0.17889 (19)	0.46524 (18)	0.02645 (16)	0.0309 (5)
H37	0.1614	0.4149	0.0598	0.037*
C38	0.2498 (2)	0.4349 (2)	−0.05163 (17)	0.0401 (6)
H38	0.2808	0.3642	−0.0712	0.048*
C39	0.2754 (2)	0.5066 (2)	−0.10083 (17)	0.0419 (6)
H39	0.3262	0.4868	−0.1528	0.050*
C40	0.2270 (2)	0.6071 (2)	−0.07446 (17)	0.0416 (6)
H40	0.2429	0.6558	−0.1096	0.050*
C41	0.1557 (2)	0.63781 (19)	0.00233 (16)	0.0320 (5)
H41	0.1215	0.7068	0.0187	0.038*
C42	−0.00310 (16)	0.75312 (16)	0.34128 (15)	0.0209 (5)
C43	−0.05867 (18)	0.81701 (18)	0.42232 (16)	0.0274 (5)
H43	−0.0384	0.8152	0.4848	0.033*
C44	−0.14299 (18)	0.88309 (18)	0.41306 (17)	0.0310 (5)
H44	−0.1793	0.9274	0.4694	0.037*
C45	−0.17537 (17)	0.88550 (17)	0.32215 (17)	0.0284 (5)
C46	−0.11840 (17)	0.82177 (17)	0.24161 (16)	0.0263 (5)
H46	−0.1396	0.8231	0.1792	0.032*
C47	−0.03145 (17)	0.75615 (16)	0.24917 (15)	0.0222 (5)
C48	−0.2672 (2)	0.9570 (2)	0.3111 (2)	0.0432 (6)
H48A	−0.2339	1.0214	0.2976	0.065*
H48B	−0.3089	0.9822	0.3714	0.065*
H48C	−0.3186	0.9142	0.2571	0.065*
N3	0.09285 (14)	0.69706 (13)	0.35612 (12)	0.0215 (4)
N4	0.02928 (14)	0.70698 (14)	0.16533 (12)	0.0235 (4)
O5	0.47410 (12)	0.39866 (11)	0.20519 (11)	0.0310 (4)
O6	0.58380 (11)	0.57683 (12)	0.30791 (10)	0.0289 (4)
O7	0.21847 (12)	0.81169 (12)	0.50136 (10)	0.0318 (4)
O8	0.21966 (12)	0.86010 (11)	0.35488 (11)	0.0325 (4)
S2	0.20873 (4)	0.77439 (4)	0.39734 (4)	0.02169 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0384 (14)	0.0364 (13)	0.0432 (15)	0.0115 (11)	0.0032 (11)	0.0250 (12)
C2	0.0318 (13)	0.0387 (13)	0.0250 (13)	0.0040 (10)	0.0060 (10)	0.0130 (10)
C3	0.0219 (11)	0.0144 (10)	0.0171 (11)	−0.0015 (8)	−0.0029 (8)	0.0020 (8)
C4	0.0272 (12)	0.0181 (10)	0.0210 (11)	−0.0001 (9)	−0.0018 (9)	0.0085 (9)
C5	0.0243 (11)	0.0168 (10)	0.0257 (12)	0.0038 (9)	0.0001 (9)	0.0058 (9)
C6	0.0221 (11)	0.0213 (11)	0.0181 (11)	0.0007 (9)	0.0001 (9)	0.0028 (9)
C7	0.0250 (11)	0.0215 (11)	0.0212 (11)	0.0003 (9)	−0.0003 (9)	0.0089 (9)
C8	0.0219 (11)	0.0154 (10)	0.0197 (11)	−0.0015 (8)	−0.0028 (9)	0.0038 (8)
C9	0.0208 (11)	0.0170 (10)	0.0205 (11)	0.0008 (8)	−0.0005 (8)	0.0061 (8)
C10	0.0222 (11)	0.0209 (11)	0.0195 (11)	0.0018 (9)	0.0003 (8)	0.0061 (9)
C11	0.0229 (11)	0.0201 (11)	0.0136 (10)	0.0013 (9)	0.0003 (8)	0.0038 (8)
C12	0.0238 (11)	0.0241 (11)	0.0129 (10)	0.0015 (9)	0.0005 (8)	0.0034 (8)
C13	0.0261 (12)	0.0243 (12)	0.0271 (12)	0.0036 (9)	0.0006 (9)	0.0058 (9)
C14	0.0295 (13)	0.0343 (13)	0.0266 (13)	0.0117 (11)	−0.0012 (10)	0.0074 (10)
C15	0.0224 (12)	0.0484 (15)	0.0234 (13)	0.0033 (11)	−0.0003 (9)	0.0110 (11)
C16	0.0235 (12)	0.0401 (14)	0.0390 (14)	−0.0061 (11)	−0.0050 (10)	0.0180 (11)
C17	0.0249 (12)	0.0279 (12)	0.0306 (13)	0.0016 (10)	−0.0031 (9)	0.0123 (10)
C18	0.0211 (11)	0.0182 (10)	0.0224 (11)	0.0027 (9)	0.0023 (9)	0.0063 (9)
C19	0.0231 (11)	0.0267 (11)	0.0224 (12)	0.0012 (9)	−0.0028 (9)	0.0049 (9)
C20	0.0178 (11)	0.0305 (12)	0.0290 (13)	0.0039 (9)	−0.0006 (9)	0.0095 (10)
C21	0.0239 (11)	0.0202 (11)	0.0273 (12)	0.0037 (9)	0.0021 (9)	0.0090 (9)
C22	0.0248 (11)	0.0200 (11)	0.0227 (12)	0.0008 (9)	−0.0036 (9)	0.0037 (9)
C23	0.0215 (11)	0.0186 (10)	0.0235 (11)	−0.0001 (9)	−0.0010 (9)	0.0069 (9)
C24	0.0274 (12)	0.0310 (12)	0.0320 (13)	0.0075 (10)	0.0024 (10)	0.0074 (10)
N1	0.0225 (9)	0.0190 (9)	0.0200 (9)	0.0036 (7)	0.0003 (7)	0.0067 (7)
N2	0.0194 (9)	0.0219 (9)	0.0214 (10)	0.0016 (7)	−0.0016 (7)	0.0036 (7)
O1	0.0336 (9)	0.0255 (8)	0.0316 (9)	0.0116 (7)	0.0054 (7)	0.0131 (7)
O2	0.0317 (8)	0.0301 (8)	0.0250 (8)	0.0102 (7)	0.0094 (7)	0.0110 (7)
O3	0.0316 (8)	0.0169 (7)	0.0333 (9)	−0.0017 (6)	0.0000 (7)	0.0069 (6)
O4	0.0308 (8)	0.0269 (8)	0.0217 (8)	0.0024 (7)	−0.0058 (6)	0.0084 (6)
S1	0.0222 (3)	0.0166 (3)	0.0209 (3)	0.0006 (2)	−0.0011 (2)	0.0056 (2)
C25	0.0392 (14)	0.0256 (12)	0.0386 (14)	0.0070 (11)	−0.0016 (11)	−0.0064 (11)
C26	0.0240 (12)	0.0359 (13)	0.0395 (14)	−0.0033 (10)	0.0003 (10)	0.0072 (11)
C27	0.0199 (10)	0.0196 (11)	0.0193 (11)	0.0006 (9)	−0.0005 (8)	0.0098 (9)
C28	0.0230 (11)	0.0168 (10)	0.0243 (12)	0.0010 (9)	−0.0004 (9)	0.0053 (9)
C29	0.0280 (12)	0.0202 (11)	0.0213 (12)	0.0077 (9)	0.0028 (9)	0.0057 (9)
C30	0.0188 (11)	0.0258 (11)	0.0201 (11)	0.0022 (9)	0.0005 (8)	0.0080 (9)
C31	0.0238 (11)	0.0178 (10)	0.0203 (11)	−0.0015 (9)	−0.0015 (9)	0.0057 (9)
C32	0.0231 (11)	0.0172 (10)	0.0185 (11)	0.0022 (9)	0.0019 (8)	0.0076 (8)
C33	0.0242 (11)	0.0162 (10)	0.0210 (11)	0.0027 (9)	0.0017 (9)	0.0060 (8)
C34	0.0184 (10)	0.0183 (10)	0.0213 (11)	0.0017 (8)	0.0008 (8)	0.0037 (9)
C35	0.0207 (11)	0.0218 (11)	0.0193 (11)	−0.0007 (9)	−0.0038 (8)	0.0046 (9)
C36	0.0243 (11)	0.0217 (11)	0.0187 (11)	0.0002 (9)	−0.0014 (9)	0.0039 (9)
C37	0.0371 (13)	0.0298 (12)	0.0243 (13)	0.0038 (10)	0.0039 (10)	0.0068 (10)
C38	0.0436 (15)	0.0391 (14)	0.0313 (14)	0.0121 (12)	0.0101 (11)	0.0024 (11)
C39	0.0426 (15)	0.0534 (17)	0.0231 (13)	0.0006 (13)	0.0106 (11)	0.0046 (12)
C40	0.0554 (16)	0.0442 (15)	0.0267 (14)	−0.0024 (13)	0.0079 (12)	0.0145 (12)
C41	0.0407 (14)	0.0310 (12)	0.0237 (13)	0.0012 (11)	0.0012 (10)	0.0086 (10)
C42	0.0183 (10)	0.0191 (10)	0.0247 (12)	0.0022 (9)	0.0019 (9)	0.0065 (9)
C43	0.0256 (12)	0.0298 (12)	0.0247 (12)	0.0041 (10)	0.0021 (9)	0.0060 (10)
C44	0.0263 (12)	0.0283 (12)	0.0329 (14)	0.0087 (10)	0.0076 (10)	0.0020 (10)
C45	0.0227 (11)	0.0209 (11)	0.0386 (14)	0.0036 (9)	−0.0028 (10)	0.0059 (10)
C46	0.0257 (12)	0.0221 (11)	0.0301 (13)	0.0008 (9)	−0.0056 (9)	0.0078 (10)
C47	0.0223 (11)	0.0177 (10)	0.0248 (12)	0.0001 (9)	0.0004 (9)	0.0053 (9)
C48	0.0348 (14)	0.0366 (14)	0.0522 (17)	0.0131 (11)	−0.0065 (12)	0.0059 (12)
N3	0.0223 (9)	0.0180 (9)	0.0219 (9)	0.0034 (7)	−0.0019 (7)	0.0037 (7)
N4	0.0261 (10)	0.0224 (10)	0.0214 (10)	0.0021 (8)	−0.0008 (8)	0.0066 (8)
O5	0.0253 (8)	0.0238 (8)	0.0367 (9)	0.0079 (7)	0.0020 (7)	0.0002 (7)
O6	0.0196 (8)	0.0302 (8)	0.0313 (9)	0.0003 (6)	0.0004 (6)	0.0032 (7)
O7	0.0326 (9)	0.0336 (9)	0.0205 (8)	0.0070 (7)	−0.0052 (6)	−0.0024 (7)
O8	0.0325 (9)	0.0213 (8)	0.0480 (10)	0.0031 (7)	−0.0025 (7)	0.0172 (7)
S2	0.0230 (3)	0.0175 (3)	0.0231 (3)	0.0027 (2)	−0.0020 (2)	0.0048 (2)

Geometric parameters (Å, º) top

C1—O1	1.433 (2)	C25—O5	1.437 (3)
C1—H1A	0.9800	C25—H25A	0.9800
C1—H1B	0.9800	C25—H25B	0.9800
C1—H1C	0.9800	C25—H25C	0.9800
C2—O2	1.424 (2)	C26—O6	1.429 (3)
C2—H2A	0.9800	C26—H26A	0.9800
C2—H2B	0.9800	C26—H26B	0.9800
C2—H2C	0.9800	C26—H26C	0.9800
C3—C8	1.367 (3)	C27—C32	1.373 (3)
C3—C4	1.394 (3)	C27—C28	1.390 (3)
C3—C9	1.505 (3)	C27—C33	1.517 (3)
C4—C5	1.378 (3)	C28—C29	1.385 (3)
C4—H4	0.9500	C28—H28	0.9500
C5—O1	1.362 (2)	C29—O5	1.354 (2)
C5—C6	1.418 (3)	C29—C30	1.415 (3)
C6—O2	1.364 (2)	C30—O6	1.365 (2)
C6—C7	1.377 (3)	C30—C31	1.370 (3)
C7—C8	1.398 (3)	C31—C32	1.395 (3)
C7—H7	0.9500	C31—H31	0.9500
C8—S1	1.740 (2)	C32—S2	1.730 (2)
C9—N1	1.482 (2)	C33—N3	1.484 (3)
C9—C10	1.528 (3)	C33—C34	1.528 (3)
C9—H9	1.0000	C33—H33	1.0000
C10—C11	1.514 (3)	C34—C35	1.512 (3)
C10—H10A	0.9900	C34—H34A	0.9900
C10—H10B	0.9900	C34—H34B	0.9900
C11—N2	1.286 (2)	C35—N4	1.285 (3)
C11—C12	1.488 (3)	C35—C36	1.482 (3)
C12—C13	1.388 (3)	C36—C37	1.388 (3)
C12—C17	1.397 (3)	C36—C41	1.399 (3)
C13—C14	1.393 (3)	C37—C38	1.386 (3)
C13—H13	0.9500	C37—H37	0.9500
C14—C15	1.374 (3)	C38—C39	1.374 (3)
C14—H14	0.9500	C38—H38	0.9500
C15—C16	1.383 (3)	C39—C40	1.374 (4)
C15—H15	0.9500	C39—H39	0.9500
C16—C17	1.381 (3)	C40—C41	1.376 (3)
C16—H16	0.9500	C40—H40	0.9500
C17—H17	0.9500	C41—H41	0.9500
C18—C19	1.384 (3)	C42—C43	1.388 (3)
C18—C23	1.408 (3)	C42—C47	1.398 (3)
C18—N1	1.430 (3)	C42—N3	1.432 (3)
C19—C20	1.382 (3)	C43—C44	1.380 (3)
C19—H19	0.9500	C43—H43	0.9500
C20—C21	1.392 (3)	C44—C45	1.390 (3)
C20—H20	0.9500	C44—H44	0.9500
C21—C22	1.391 (3)	C45—C46	1.392 (3)
C21—C24	1.504 (3)	C45—C48	1.503 (3)
C22—C23	1.384 (3)	C46—C47	1.393 (3)
C22—H22	0.9500	C46—H46	0.9500
C23—N2	1.413 (3)	C47—N4	1.402 (3)
C24—H24A	0.9800	C48—H48A	0.9800
C24—H24B	0.9800	C48—H48B	0.9800
C24—H24C	0.9800	C48—H48C	0.9800
N1—S1	1.6479 (16)	N3—S2	1.6406 (17)
O3—S1	1.4374 (14)	O7—S2	1.4321 (15)
O4—S1	1.4295 (14)	O8—S2	1.4383 (15)

O1—C1—H1A	109.5	O5—C25—H25A	109.5
O1—C1—H1B	109.5	O5—C25—H25B	109.5
H1A—C1—H1B	109.5	H25A—C25—H25B	109.5
O1—C1—H1C	109.5	O5—C25—H25C	109.5
H1A—C1—H1C	109.5	H25A—C25—H25C	109.5
H1B—C1—H1C	109.5	H25B—C25—H25C	109.5
O2—C2—H2A	109.5	O6—C26—H26A	109.5
O2—C2—H2B	109.5	O6—C26—H26B	109.5
H2A—C2—H2B	109.5	H26A—C26—H26B	109.5
O2—C2—H2C	109.5	O6—C26—H26C	109.5
H2A—C2—H2C	109.5	H26A—C26—H26C	109.5
H2B—C2—H2C	109.5	H26B—C26—H26C	109.5
C8—C3—C4	119.80 (19)	C32—C27—C28	119.02 (18)
C8—C3—C9	114.71 (17)	C32—C27—C33	114.27 (17)
C4—C3—C9	125.35 (17)	C28—C27—C33	126.65 (17)
C5—C4—C3	118.94 (18)	C29—C28—C27	119.12 (18)
C5—C4—H4	120.5	C29—C28—H28	120.4
C3—C4—H4	120.5	C27—C28—H28	120.4
O1—C5—C4	124.86 (18)	O5—C29—C28	124.54 (18)
O1—C5—C6	114.49 (17)	O5—C29—C30	114.72 (17)
C4—C5—C6	120.65 (18)	C28—C29—C30	120.74 (18)
O2—C6—C7	125.27 (18)	O6—C30—C31	125.14 (18)
O2—C6—C5	114.49 (17)	O6—C30—C29	114.80 (17)
C7—C6—C5	120.23 (18)	C31—C30—C29	120.06 (18)
C6—C7—C8	117.64 (18)	C30—C31—C32	117.85 (18)
C6—C7—H7	121.2	C30—C31—H31	121.1
C8—C7—H7	121.2	C32—C31—H31	121.1
C3—C8—C7	122.65 (18)	C27—C32—C31	123.09 (18)
C3—C8—S1	111.35 (15)	C27—C32—S2	111.58 (15)
C7—C8—S1	125.92 (15)	C31—C32—S2	125.30 (15)
N1—C9—C3	105.11 (15)	N3—C33—C27	104.51 (15)
N1—C9—C10	111.04 (15)	N3—C33—C34	110.71 (15)
C3—C9—C10	114.78 (16)	C27—C33—C34	116.61 (16)
N1—C9—H9	108.6	N3—C33—H33	108.2
C3—C9—H9	108.6	C27—C33—H33	108.2
C10—C9—H9	108.6	C34—C33—H33	108.2
C11—C10—C9	111.25 (15)	C35—C34—C33	112.47 (16)
C11—C10—H10A	109.4	C35—C34—H34A	109.1
C9—C10—H10A	109.4	C33—C34—H34A	109.1
C11—C10—H10B	109.4	C35—C34—H34B	109.1
C9—C10—H10B	109.4	C33—C34—H34B	109.1
H10A—C10—H10B	108.0	H34A—C34—H34B	107.8
N2—C11—C12	117.02 (17)	N4—C35—C36	116.87 (18)
N2—C11—C10	121.73 (17)	N4—C35—C34	122.00 (18)
C12—C11—C10	121.24 (17)	C36—C35—C34	121.12 (17)
C13—C12—C17	118.26 (19)	C37—C36—C41	118.0 (2)
C13—C12—C11	122.76 (18)	C37—C36—C35	123.05 (18)
C17—C12—C11	118.97 (18)	C41—C36—C35	118.94 (19)
C12—C13—C14	120.3 (2)	C38—C37—C36	120.7 (2)
C12—C13—H13	119.8	C38—C37—H37	119.6
C14—C13—H13	119.8	C36—C37—H37	119.6
C15—C14—C13	120.8 (2)	C39—C38—C37	120.3 (2)
C15—C14—H14	119.6	C39—C38—H38	119.8
C13—C14—H14	119.6	C37—C38—H38	119.8
C14—C15—C16	119.4 (2)	C38—C39—C40	119.6 (2)
C14—C15—H15	120.3	C38—C39—H39	120.2
C16—C15—H15	120.3	C40—C39—H39	120.2
C17—C16—C15	120.3 (2)	C39—C40—C41	120.7 (2)
C17—C16—H16	119.8	C39—C40—H40	119.7
C15—C16—H16	119.8	C41—C40—H40	119.7
C16—C17—C12	120.9 (2)	C40—C41—C36	120.6 (2)
C16—C17—H17	119.5	C40—C41—H41	119.7
C12—C17—H17	119.5	C36—C41—H41	119.7
C19—C18—C23	118.93 (18)	C43—C42—C47	120.06 (19)
C19—C18—N1	120.14 (18)	C43—C42—N3	118.37 (18)
C23—C18—N1	120.92 (17)	C47—C42—N3	121.01 (17)
C20—C19—C18	121.32 (19)	C44—C43—C42	120.7 (2)
C20—C19—H19	119.3	C44—C43—H43	119.6
C18—C19—H19	119.3	C42—C43—H43	119.6
C19—C20—C21	120.70 (19)	C43—C44—C45	120.6 (2)
C19—C20—H20	119.6	C43—C44—H44	119.7
C21—C20—H20	119.6	C45—C44—H44	119.7
C22—C21—C20	117.61 (19)	C44—C45—C46	118.09 (19)
C22—C21—C24	120.97 (18)	C44—C45—C48	121.1 (2)
C20—C21—C24	121.42 (18)	C46—C45—C48	120.8 (2)
C23—C22—C21	122.67 (19)	C45—C46—C47	122.4 (2)
C23—C22—H22	118.7	C45—C46—H46	118.8
C21—C22—H22	118.7	C47—C46—H46	118.8
C22—C23—C18	118.72 (18)	C46—C47—C42	118.05 (19)
C22—C23—N2	118.58 (17)	C46—C47—N4	117.27 (18)
C18—C23—N2	122.55 (18)	C42—C47—N4	124.33 (18)
C21—C24—H24A	109.5	C45—C48—H48A	109.5
C21—C24—H24B	109.5	C45—C48—H48B	109.5
H24A—C24—H24B	109.5	H48A—C48—H48B	109.5
C21—C24—H24C	109.5	C45—C48—H48C	109.5
H24A—C24—H24C	109.5	H48A—C48—H48C	109.5
H24B—C24—H24C	109.5	H48B—C48—H48C	109.5
C18—N1—C9	120.90 (15)	C42—N3—C33	123.39 (16)
C18—N1—S1	118.90 (13)	C42—N3—S2	116.39 (12)
C9—N1—S1	115.15 (13)	C33—N3—S2	115.50 (13)
C11—N2—C23	120.09 (16)	C35—N4—C47	121.94 (17)
C5—O1—C1	117.25 (16)	C29—O5—C25	116.94 (16)
C6—O2—C2	117.44 (16)	C30—O6—C26	117.05 (16)
O4—S1—O3	114.70 (8)	O7—S2—O8	115.28 (9)
O4—S1—N1	112.29 (8)	O7—S2—N3	111.89 (9)
O3—S1—N1	110.02 (8)	O8—S2—N3	110.19 (9)
O4—S1—C8	111.83 (9)	O7—S2—C32	111.60 (9)
O3—S1—C8	112.54 (9)	O8—S2—C32	112.07 (9)
N1—S1—C8	93.60 (9)	N3—S2—C32	93.86 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···O1ⁱ	0.98	2.59	3.423 (3)	142
C4—H4···O8ⁱⁱ	0.95	2.55	3.451 (3)	157
C10—H10B···O8ⁱⁱ	0.99	2.43	3.408 (3)	171
C13—H13···O8ⁱⁱ	0.95	2.35	3.295 (3)	174
C15—H15···O7ⁱⁱⁱ	0.95	2.55	3.428 (3)	153
C25—H25B···O2ⁱ	0.98	2.35	3.262 (3)	154
C28—H28···O3	0.95	2.27	3.205 (3)	169
C34—H34A···O3	0.99	2.60	3.552 (3)	162
C37—H37···O3	0.95	2.43	3.371 (3)	170
C39—H39···O6^iv	0.95	2.42	3.350 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₂O₄S
M_r	434.51
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	11.9007 (4), 12.8521 (4), 14.6202 (5)
α, β, γ (°)	109.852 (2), 90.743 (2), 92.775 (2)
V (Å³)	2099.76 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.50 × 0.30 × 0.10

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.912, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	31054, 7393, 5463
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.01
No. of reflections	7393
No. of parameters	566
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.46

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), COLLECT (Hooft, 1998) and maXus (Mackay et al., 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CAMERON (Watkin, et al., 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···O1ⁱ	0.98	2.59	3.423 (3)	142
C4—H4···O8ⁱⁱ	0.95	2.55	3.451 (3)	157
C10—H10B···O8ⁱⁱ	0.99	2.43	3.408 (3)	171
C13—H13···O8ⁱⁱ	0.95	2.35	3.295 (3)	174
C15—H15···O7ⁱⁱⁱ	0.95	2.55	3.428 (3)	153
C25—H25B···O2ⁱ	0.98	2.35	3.262 (3)	154
C28—H28···O3	0.95	2.27	3.205 (3)	169
C34—H34A···O3	0.99	2.60	3.552 (3)	162
C37—H37···O3	0.95	2.43	3.371 (3)	170
C39—H39···O6^iv	0.95	2.42	3.350 (3)	167

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

Acknowledgements

We thank the EPSRC for funding the National Crystallography Service, and the STFC (formerly CCLRC) for access to synchrotron facilities.

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Volume 67| Part 3| March 2011| Pages o684-o685

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

Racemic 9,10-dimeth­­oxy-3-methyl-6-phenyl-7,7a-di­hydro­benzo[b]benzo[4,5]iso­thia­zolo[2,3-d][1,4]diazepine 12,12-dioxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Racemic 9,10-dimethoxy-3-methyl-6-phenyl-7,7a-dihydrobenzo[b]benzo[4,5]isothiazolo[2,3-d][1,4]diazepine 12,12-dioxide