Benzyl N′-(4,6-dimeth­oxy-2-methyl-3-phenyl-1H-indol-7-ylmethyl­ene)hydrazinecarbodithio­ate

Khaldei, H.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536808038592

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2442

doi:10.1107/S1600536808038592

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Benzyl N′-(4,6-dimethoxy-2-methyl-3-phenyl-1H-indol-7-ylmethylene)hydrazinecarbodithioate

Hamid Khaldei,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 November 2008; accepted 19 November 2008; online 26 November 2008)

The asymmetric unit of the title compound, C₂₆H₂₅N₃O₂S₂, contains two independent molecules, which are linked by a pair of N—H⋯S hydrogen bonds, forming a dimer.

Related literature

For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008 ). For further synthetic details, see: Ali & Tarafder (1977 ); Jones et al. (2005 ).

Experimental

Crystal data

C₂₆H₂₅N₃O₂S₂
M_r = 475.61
Triclinic, $[P \overline 1]$
a = 10.0913 (2) Å
b = 12.8541 (3) Å
c = 18.9232 (4) Å
α = 90.461 (1)°
β = 103.960 (1)°
γ = 93.944 (1)°
V = 2375.71 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 (2) K
0.40 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.906, T_max = 0.975
22819 measured reflections
10887 independent reflections
7429 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.145
S = 1.01
10887 reflections
601 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S4	0.88	2.47	3.330 (2)	164
N4—H4⋯S2	0.88	2.50	3.368 (2)	170

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: pubCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038592/hb2850sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038592/hb2850Isup2.hkl

checkCIF report

Comment top

For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008). For further synthetic details, see: Ali & Tarafder (1977); Jones et al. (2005).

Related literature top

For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008). For further synthetic details, see: Ali & Tarafder (1977); Jones et al. (2005).

Experimental top

4,6-Dimethoxy-2-methyl-3-phenylindole-7-carbaldehyde was prepared by using a literature method (Jones et al., 2005) as was S-benzyl dithiocarbazate (Ali & Tarafder, 1977). 4,6-Dimethoxy-2-methyl-3-phenylindole-7-carbaldehyde (0.59 g, 2 mmol) and S-benzyl dithiocarbazate (0.40 g, 2 mmol) were refluxed in ethanol (40 ml) for 6 h. About 1 ml acetic acid was also added. The precipitate was filtered, washed with cold ethanol and dried. Yellow prisms of (I) were grown by slow evaporation of a DMF solution at room temperature

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2008).

Figures top

Fig. 1. The molecular structure of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

Benzyl N'-(4,6-dimethoxy-2-methyl-3-phenyl-1H- indol-7-ylmethylene)hydrazinecarbodithioate top

Crystal data top

C₂₆H₂₅N₃O₂S₂	Z = 4
M_r = 475.61	F(000) = 1000
Triclinic, P1	D_x = 1.330 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0913 (2) Å	Cell parameters from 3627 reflections
b = 12.8541 (3) Å	θ = 2.2–27.9°
c = 18.9232 (4) Å	µ = 0.25 mm⁻¹
α = 90.461 (1)°	T = 100 K
β = 103.960 (1)°	Prism, yellow
γ = 93.944 (1)°	0.40 × 0.15 × 0.10 mm
V = 2375.71 (9) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	10887 independent reflections
Radiation source: fine-focus sealed tube	7429 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.906, T_max = 0.975	k = −16→16
22819 measured reflections	l = −24→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0761P)²] where P = (F_o² + 2F_c²)/3
10887 reflections	(Δ/σ)_max = 0.001
601 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₆H₂₅N₃O₂S₂	γ = 93.944 (1)°
M_r = 475.61	V = 2375.71 (9) Å³
Triclinic, P1	Z = 4
a = 10.0913 (2) Å	Mo Kα radiation
b = 12.8541 (3) Å	µ = 0.25 mm⁻¹
c = 18.9232 (4) Å	T = 100 K
α = 90.461 (1)°	0.40 × 0.15 × 0.10 mm
β = 103.960 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	10887 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7429 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.975	R_int = 0.037
22819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	Δρ_max = 0.38 e Å⁻³
10887 reflections	Δρ_min = −0.33 e Å⁻³
601 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.70730 (6)	0.77337 (4)	0.38863 (3)	0.02192 (14)
S2	0.86760 (6)	0.64215 (4)	0.50774 (3)	0.02258 (14)
S3	0.76473 (6)	0.21326 (4)	0.59896 (3)	0.02381 (15)
S4	0.61229 (6)	0.34616 (5)	0.47915 (3)	0.02475 (15)
N1	0.62636 (18)	0.58880 (14)	0.41970 (10)	0.0203 (4)
H1	0.6232	0.5309	0.4439	0.024*
N2	0.52245 (19)	0.60752 (14)	0.35981 (10)	0.0193 (4)
N3	0.41658 (18)	0.70701 (13)	0.23268 (9)	0.0168 (4)
H3	0.4872	0.7206	0.2700	0.020*
N4	0.84585 (19)	0.40040 (14)	0.57324 (10)	0.0214 (4)
H4	0.8499	0.4595	0.5504	0.026*
N5	0.94526 (19)	0.38083 (14)	0.63461 (9)	0.0199 (4)
N6	1.04365 (18)	0.27207 (13)	0.75800 (9)	0.0173 (4)
H6	0.9726	0.2628	0.7205	0.021*
O1	0.18934 (16)	0.40290 (12)	0.31166 (8)	0.0241 (4)
O2	0.01662 (15)	0.56662 (12)	0.08209 (8)	0.0211 (3)
O3	1.27723 (16)	0.58543 (12)	0.69482 (8)	0.0249 (4)
O4	1.44777 (15)	0.39642 (12)	0.91349 (8)	0.0204 (3)
C1	0.8502 (2)	0.95402 (18)	0.38428 (13)	0.0234 (5)
C2	0.8241 (3)	0.95499 (19)	0.30847 (14)	0.0301 (6)
H2	0.8166	0.8911	0.2817	0.036*
C3	0.8088 (3)	1.0478 (2)	0.27173 (15)	0.0346 (6)
H3A	0.7898	1.0476	0.2201	0.042*
C4	0.8215 (3)	1.1411 (2)	0.31081 (16)	0.0365 (7)
H4A	0.8129	1.2050	0.2858	0.044*
C5	0.8463 (3)	1.1416 (2)	0.38548 (16)	0.0362 (7)
H5	0.8540	1.2057	0.4120	0.043*
C6	0.8600 (2)	1.04831 (19)	0.42195 (14)	0.0301 (6)
H6A	0.8764	1.0490	0.4735	0.036*
C7	0.8656 (2)	0.85233 (17)	0.42390 (13)	0.0240 (5)
H7A	0.8807	0.8648	0.4770	0.029*
H7B	0.9442	0.8171	0.4146	0.029*
C8	0.7315 (2)	0.66011 (17)	0.44022 (11)	0.0181 (5)
C9	0.4171 (2)	0.54120 (17)	0.34579 (12)	0.0192 (5)
H9	0.4101	0.4862	0.3782	0.023*
C10	0.3103 (2)	0.55083 (17)	0.28101 (11)	0.0170 (4)
C11	0.1969 (2)	0.47839 (17)	0.26171 (12)	0.0191 (5)
C12	0.0981 (2)	0.48203 (17)	0.19613 (11)	0.0187 (5)
H12	0.0228	0.4311	0.1852	0.022*
C13	0.1091 (2)	0.55997 (17)	0.14656 (11)	0.0176 (5)
C14	0.2202 (2)	0.63542 (16)	0.16222 (11)	0.0165 (4)
C15	0.3166 (2)	0.62922 (16)	0.22955 (11)	0.0163 (4)
C16	0.3911 (2)	0.76147 (16)	0.16888 (11)	0.0166 (4)
C17	0.4871 (2)	0.85195 (17)	0.16129 (12)	0.0218 (5)
H17A	0.4500	0.8876	0.1160	0.033*
H17B	0.5762	0.8270	0.1602	0.033*
H17C	0.4983	0.9007	0.2028	0.033*
C18	0.2714 (2)	0.72033 (16)	0.12301 (11)	0.0173 (4)
C19	0.2177 (2)	0.75254 (17)	0.04715 (11)	0.0189 (5)
C20	0.3054 (2)	0.76263 (17)	0.00017 (12)	0.0228 (5)
H20	0.3986	0.7483	0.0172	0.027*
C21	0.2575 (2)	0.79344 (19)	−0.07118 (12)	0.0271 (5)
H21	0.3179	0.7993	−0.1027	0.033*
C22	0.1218 (3)	0.81568 (19)	−0.09653 (13)	0.0285 (6)
H22	0.0892	0.8376	−0.1451	0.034*
C23	0.0345 (2)	0.80567 (18)	−0.05034 (12)	0.0252 (5)
H23	−0.0585	0.8207	−0.0674	0.030*
C24	0.0814 (2)	0.77397 (17)	0.02037 (12)	0.0203 (5)
H24	0.0198	0.7667	0.0512	0.024*
C25	0.0776 (2)	0.32470 (17)	0.29397 (13)	0.0256 (5)
H25A	0.0825	0.2777	0.3349	0.038*
H25B	0.0830	0.2847	0.2506	0.038*
H25C	−0.0091	0.3582	0.2843	0.038*
C26	−0.0941 (2)	0.48780 (17)	0.06387 (12)	0.0214 (5)
H26A	−0.1508	0.5000	0.0152	0.032*
H26B	−0.1499	0.4903	0.0996	0.032*
H26C	−0.0575	0.4191	0.0643	0.032*
C27	0.6207 (2)	0.03069 (18)	0.59376 (13)	0.0245 (5)
C28	0.5762 (3)	0.0196 (2)	0.65644 (16)	0.0462 (8)
H28	0.5381	0.0764	0.6750	0.056*
C29	0.5862 (4)	−0.0736 (2)	0.69306 (18)	0.0581 (10)
H29	0.5548	−0.0801	0.7364	0.070*
C30	0.6409 (3)	−0.1562 (2)	0.66741 (16)	0.0391 (7)
H30	0.6501	−0.2191	0.6936	0.047*
C31	0.6823 (3)	−0.1476 (2)	0.60373 (15)	0.0362 (6)
H31	0.7176	−0.2054	0.5847	0.043*
C32	0.6726 (3)	−0.0545 (2)	0.56714 (14)	0.0310 (6)
H32	0.7019	−0.0489	0.5232	0.037*
C33	0.6132 (2)	0.13207 (18)	0.55449 (13)	0.0240 (5)
H33A	0.5295	0.1660	0.5576	0.029*
H33B	0.6112	0.1200	0.5025	0.029*
C34	0.7437 (2)	0.32828 (17)	0.54922 (12)	0.0202 (5)
C35	1.1528 (2)	0.43417 (16)	0.71813 (11)	0.0179 (5)
C36	1.0496 (2)	0.44792 (17)	0.65222 (11)	0.0193 (5)
H36	1.0583	0.5056	0.6221	0.023*
C37	1.2684 (2)	0.50485 (17)	0.74051 (12)	0.0200 (5)
C38	1.3671 (2)	0.49319 (17)	0.80491 (12)	0.0191 (5)
H38	1.4446	0.5420	0.8179	0.023*
C39	1.3533 (2)	0.41075 (17)	0.85036 (11)	0.0176 (4)
C40	1.2386 (2)	0.33879 (16)	0.83225 (11)	0.0161 (4)
C41	1.1435 (2)	0.35199 (16)	0.76586 (11)	0.0160 (4)
C42	1.0701 (2)	0.20814 (16)	0.81719 (12)	0.0178 (5)
C43	0.9715 (2)	0.11756 (17)	0.82004 (12)	0.0229 (5)
H43A	0.9975	0.0852	0.8677	0.034*
H43B	0.9731	0.0664	0.7816	0.034*
H43C	0.8791	0.1414	0.8127	0.034*
C44	1.1897 (2)	0.24588 (16)	0.86497 (11)	0.0166 (4)
C45	1.2495 (2)	0.20264 (17)	0.93687 (12)	0.0195 (5)
C46	1.2650 (2)	0.09692 (18)	0.94606 (13)	0.0270 (5)
H46	1.2390	0.0507	0.9048	0.032*
C47	1.3176 (3)	0.0574 (2)	1.01393 (14)	0.0383 (7)
H47	1.3266	−0.0155	1.0188	0.046*
C48	1.3569 (3)	0.1223 (2)	1.07449 (14)	0.0367 (7)
H48	1.3931	0.0949	1.1211	0.044*
C49	1.3433 (2)	0.2282 (2)	1.06674 (13)	0.0279 (6)
H49	1.3708	0.2740	1.1082	0.033*
C50	1.2897 (2)	0.26779 (18)	0.99898 (12)	0.0219 (5)
H50	1.2800	0.3406	0.9945	0.026*
C51	1.3965 (2)	0.65652 (17)	0.71292 (13)	0.0248 (5)
H51A	1.3928	0.7072	0.6742	0.037*
H51B	1.4785	0.6178	0.7180	0.037*
H51C	1.3999	0.6933	0.7590	0.037*
C52	1.5632 (2)	0.47112 (18)	0.93250 (13)	0.0233 (5)
H52A	1.6237	0.4522	0.9786	0.035*
H52B	1.5316	0.5405	0.9378	0.035*
H52C	1.6132	0.4718	0.8941	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0212 (3)	0.0182 (3)	0.0231 (3)	−0.0008 (2)	−0.0005 (2)	0.0060 (2)
S2	0.0217 (3)	0.0223 (3)	0.0195 (3)	−0.0002 (2)	−0.0030 (2)	0.0042 (2)
S3	0.0245 (3)	0.0190 (3)	0.0235 (3)	−0.0007 (2)	−0.0023 (2)	0.0060 (2)
S4	0.0255 (3)	0.0232 (3)	0.0202 (3)	−0.0007 (2)	−0.0042 (2)	0.0051 (2)
N1	0.0210 (10)	0.0183 (10)	0.0185 (10)	−0.0001 (8)	−0.0009 (8)	0.0070 (8)
N2	0.0209 (10)	0.0190 (10)	0.0161 (9)	0.0012 (8)	0.0004 (7)	0.0031 (7)
N3	0.0159 (9)	0.0170 (9)	0.0156 (9)	−0.0008 (7)	0.0006 (7)	0.0035 (7)
N4	0.0241 (10)	0.0185 (10)	0.0193 (10)	0.0005 (8)	0.0011 (8)	0.0067 (8)
N5	0.0210 (10)	0.0213 (10)	0.0142 (9)	0.0016 (8)	−0.0019 (7)	0.0035 (8)
N6	0.0179 (9)	0.0152 (9)	0.0164 (9)	−0.0003 (7)	−0.0001 (7)	0.0008 (7)
O1	0.0255 (9)	0.0217 (8)	0.0206 (8)	−0.0073 (7)	−0.0008 (7)	0.0080 (7)
O2	0.0172 (8)	0.0232 (8)	0.0181 (8)	−0.0041 (6)	−0.0038 (6)	0.0021 (6)
O3	0.0262 (9)	0.0205 (8)	0.0244 (9)	−0.0060 (7)	0.0007 (7)	0.0077 (7)
O4	0.0156 (8)	0.0208 (8)	0.0214 (8)	−0.0027 (6)	−0.0011 (6)	0.0017 (6)
C1	0.0164 (11)	0.0212 (12)	0.0325 (13)	0.0000 (9)	0.0059 (10)	0.0007 (10)
C2	0.0337 (14)	0.0232 (13)	0.0379 (15)	0.0024 (11)	0.0172 (12)	0.0036 (11)
C3	0.0397 (16)	0.0309 (15)	0.0378 (15)	0.0023 (12)	0.0180 (12)	0.0100 (12)
C4	0.0293 (14)	0.0256 (14)	0.0568 (19)	0.0000 (11)	0.0149 (13)	0.0158 (13)
C5	0.0280 (14)	0.0189 (13)	0.0583 (19)	−0.0038 (11)	0.0059 (13)	−0.0034 (12)
C6	0.0244 (13)	0.0258 (13)	0.0362 (15)	−0.0052 (10)	0.0021 (11)	−0.0013 (11)
C7	0.0190 (12)	0.0205 (12)	0.0299 (13)	−0.0001 (9)	0.0011 (10)	0.0026 (10)
C8	0.0200 (11)	0.0173 (11)	0.0169 (11)	0.0009 (9)	0.0041 (9)	0.0022 (9)
C9	0.0221 (11)	0.0166 (11)	0.0181 (11)	−0.0006 (9)	0.0038 (9)	0.0037 (9)
C10	0.0181 (11)	0.0183 (11)	0.0140 (10)	0.0009 (9)	0.0030 (8)	0.0010 (8)
C11	0.0193 (11)	0.0175 (11)	0.0205 (11)	−0.0002 (9)	0.0050 (9)	0.0044 (9)
C12	0.0182 (11)	0.0196 (11)	0.0171 (11)	−0.0020 (9)	0.0027 (9)	0.0001 (9)
C13	0.0170 (11)	0.0207 (11)	0.0145 (11)	0.0030 (9)	0.0021 (8)	−0.0010 (9)
C14	0.0160 (11)	0.0175 (11)	0.0160 (11)	0.0024 (9)	0.0034 (8)	0.0003 (8)
C15	0.0172 (11)	0.0152 (11)	0.0162 (11)	−0.0005 (8)	0.0041 (8)	0.0006 (8)
C16	0.0170 (11)	0.0170 (11)	0.0162 (11)	0.0035 (9)	0.0045 (8)	0.0047 (8)
C17	0.0240 (12)	0.0210 (12)	0.0185 (11)	−0.0012 (9)	0.0021 (9)	0.0052 (9)
C18	0.0190 (11)	0.0159 (11)	0.0169 (11)	0.0028 (9)	0.0036 (8)	0.0035 (8)
C19	0.0208 (11)	0.0173 (11)	0.0165 (11)	−0.0029 (9)	0.0019 (9)	0.0020 (9)
C20	0.0217 (12)	0.0230 (12)	0.0220 (12)	−0.0010 (9)	0.0025 (9)	0.0032 (10)
C21	0.0299 (13)	0.0311 (14)	0.0198 (12)	−0.0049 (11)	0.0067 (10)	0.0056 (10)
C22	0.0335 (14)	0.0278 (14)	0.0188 (12)	−0.0073 (11)	−0.0017 (10)	0.0078 (10)
C23	0.0245 (12)	0.0217 (12)	0.0248 (13)	−0.0013 (10)	−0.0026 (10)	0.0040 (10)
C24	0.0216 (12)	0.0188 (12)	0.0191 (11)	−0.0005 (9)	0.0028 (9)	0.0024 (9)
C25	0.0278 (13)	0.0189 (12)	0.0268 (13)	−0.0069 (10)	0.0022 (10)	0.0049 (10)
C26	0.0179 (11)	0.0219 (12)	0.0216 (12)	−0.0025 (9)	0.0005 (9)	−0.0005 (9)
C27	0.0241 (12)	0.0207 (12)	0.0272 (13)	−0.0010 (10)	0.0042 (10)	0.0003 (10)
C28	0.072 (2)	0.0321 (16)	0.0483 (18)	0.0202 (15)	0.0366 (16)	0.0111 (13)
C29	0.087 (3)	0.0443 (19)	0.061 (2)	0.0224 (18)	0.048 (2)	0.0269 (16)
C30	0.0377 (16)	0.0240 (14)	0.0577 (19)	0.0025 (12)	0.0152 (14)	0.0150 (13)
C31	0.0368 (15)	0.0245 (14)	0.0447 (17)	0.0063 (12)	0.0036 (13)	−0.0018 (12)
C32	0.0305 (14)	0.0316 (14)	0.0304 (14)	0.0048 (11)	0.0058 (11)	−0.0009 (11)
C33	0.0205 (12)	0.0227 (12)	0.0262 (13)	−0.0032 (9)	0.0018 (10)	0.0025 (10)
C34	0.0228 (12)	0.0206 (12)	0.0164 (11)	0.0023 (9)	0.0030 (9)	0.0026 (9)
C35	0.0198 (11)	0.0158 (11)	0.0175 (11)	0.0027 (9)	0.0027 (9)	0.0017 (9)
C36	0.0231 (12)	0.0171 (11)	0.0179 (11)	0.0029 (9)	0.0047 (9)	0.0030 (9)
C37	0.0226 (12)	0.0150 (11)	0.0237 (12)	0.0028 (9)	0.0079 (9)	0.0031 (9)
C38	0.0172 (11)	0.0162 (11)	0.0229 (12)	−0.0020 (9)	0.0042 (9)	0.0003 (9)
C39	0.0166 (11)	0.0179 (11)	0.0175 (11)	0.0031 (9)	0.0024 (8)	−0.0017 (9)
C40	0.0172 (11)	0.0151 (11)	0.0158 (11)	0.0024 (8)	0.0034 (8)	0.0005 (8)
C41	0.0169 (11)	0.0139 (10)	0.0166 (11)	0.0005 (8)	0.0031 (8)	0.0002 (8)
C42	0.0193 (11)	0.0158 (11)	0.0180 (11)	0.0011 (9)	0.0042 (9)	0.0012 (9)
C43	0.0248 (12)	0.0187 (12)	0.0222 (12)	−0.0038 (9)	0.0017 (9)	0.0005 (9)
C44	0.0186 (11)	0.0139 (10)	0.0172 (11)	0.0011 (8)	0.0041 (8)	0.0007 (8)
C45	0.0169 (11)	0.0212 (12)	0.0201 (11)	0.0000 (9)	0.0041 (9)	0.0050 (9)
C46	0.0335 (14)	0.0222 (13)	0.0228 (12)	0.0041 (11)	0.0014 (10)	0.0027 (10)
C47	0.0569 (18)	0.0223 (14)	0.0312 (15)	0.0051 (13)	0.0008 (13)	0.0099 (11)
C48	0.0413 (16)	0.0384 (16)	0.0261 (14)	0.0029 (13)	−0.0006 (12)	0.0151 (12)
C49	0.0273 (13)	0.0331 (14)	0.0195 (12)	−0.0048 (11)	0.0003 (10)	0.0010 (10)
C50	0.0206 (12)	0.0218 (12)	0.0220 (12)	−0.0015 (9)	0.0035 (9)	0.0007 (9)
C51	0.0277 (13)	0.0185 (12)	0.0278 (13)	−0.0036 (10)	0.0073 (10)	0.0043 (10)
C52	0.0181 (11)	0.0234 (12)	0.0260 (13)	−0.0036 (9)	0.0016 (9)	−0.0017 (10)

Geometric parameters (Å, º) top

S1—C8	1.758 (2)	C20—H20	0.9500
S1—C7	1.811 (2)	C21—C22	1.388 (3)
S2—C8	1.666 (2)	C21—H21	0.9500
S3—C34	1.757 (2)	C22—C23	1.384 (3)
S3—C33	1.812 (2)	C22—H22	0.9500
S4—C34	1.664 (2)	C23—C24	1.382 (3)
N1—C8	1.333 (3)	C23—H23	0.9500
N1—N2	1.381 (2)	C24—H24	0.9500
N1—H1	0.8800	C25—H25A	0.9800
N2—C9	1.290 (3)	C25—H25B	0.9800
N3—C15	1.361 (3)	C25—H25C	0.9800
N3—C16	1.379 (3)	C26—H26A	0.9800
N3—H3	0.8800	C26—H26B	0.9800
N4—C34	1.328 (3)	C26—H26C	0.9800
N4—N5	1.377 (2)	C27—C28	1.371 (3)
N4—H4	0.8800	C27—C32	1.387 (3)
N5—C36	1.290 (3)	C27—C33	1.503 (3)
N6—C41	1.370 (3)	C28—C29	1.386 (4)
N6—C42	1.379 (3)	C28—H28	0.9500
N6—H6	0.8800	C29—C30	1.367 (4)
O1—C11	1.371 (2)	C29—H29	0.9500
O1—C25	1.432 (3)	C30—C31	1.370 (4)
O2—C13	1.353 (2)	C30—H30	0.9500
O2—C26	1.431 (2)	C31—C32	1.384 (3)
O3—C37	1.367 (3)	C31—H31	0.9500
O3—C51	1.430 (3)	C32—H32	0.9500
O4—C39	1.360 (2)	C33—H33A	0.9900
O4—C52	1.430 (3)	C33—H33B	0.9900
C1—C6	1.386 (3)	C35—C37	1.405 (3)
C1—C2	1.395 (3)	C35—C41	1.408 (3)
C1—C7	1.511 (3)	C35—C36	1.440 (3)
C2—C3	1.385 (3)	C36—H36	0.9500
C2—H2	0.9500	C37—C38	1.392 (3)
C3—C4	1.385 (4)	C38—C39	1.391 (3)
C3—H3A	0.9500	C38—H38	0.9500
C4—C5	1.374 (4)	C39—C40	1.404 (3)
C4—H4A	0.9500	C40—C41	1.404 (3)
C5—C6	1.387 (3)	C40—C44	1.460 (3)
C5—H5	0.9500	C42—C44	1.377 (3)
C6—H6A	0.9500	C42—C43	1.489 (3)
C7—H7A	0.9900	C43—H43A	0.9800
C7—H7B	0.9900	C43—H43B	0.9800
C9—C10	1.436 (3)	C43—H43C	0.9800
C9—H9	0.9500	C44—C45	1.479 (3)
C10—C11	1.398 (3)	C45—C46	1.386 (3)
C10—C15	1.416 (3)	C45—C50	1.398 (3)
C11—C12	1.395 (3)	C46—C47	1.381 (3)
C12—C13	1.395 (3)	C46—H46	0.9500
C12—H12	0.9500	C47—C48	1.374 (4)
C13—C14	1.404 (3)	C47—H47	0.9500
C14—C15	1.410 (3)	C48—C49	1.383 (4)
C14—C18	1.459 (3)	C48—H48	0.9500
C16—C18	1.375 (3)	C49—C50	1.382 (3)
C16—C17	1.492 (3)	C49—H49	0.9500
C17—H17A	0.9800	C50—H50	0.9500
C17—H17B	0.9800	C51—H51A	0.9800
C17—H17C	0.9800	C51—H51B	0.9800
C18—C19	1.480 (3)	C51—H51C	0.9800
C19—C24	1.394 (3)	C52—H52A	0.9800
C19—C20	1.398 (3)	C52—H52B	0.9800
C20—C21	1.390 (3)	C52—H52C	0.9800

C8—S1—C7	102.87 (10)	H25A—C25—H25B	109.5
C34—S3—C33	102.23 (11)	O1—C25—H25C	109.5
C8—N1—N2	118.81 (17)	H25A—C25—H25C	109.5
C8—N1—H1	120.6	H25B—C25—H25C	109.5
N2—N1—H1	120.6	O2—C26—H26A	109.5
C9—N2—N1	116.74 (18)	O2—C26—H26B	109.5
C15—N3—C16	110.09 (17)	H26A—C26—H26B	109.5
C15—N3—H3	125.0	O2—C26—H26C	109.5
C16—N3—H3	125.0	H26A—C26—H26C	109.5
C34—N4—N5	118.62 (18)	H26B—C26—H26C	109.5
C34—N4—H4	120.7	C28—C27—C32	118.3 (2)
N5—N4—H4	120.7	C28—C27—C33	121.1 (2)
C36—N5—N4	116.84 (18)	C32—C27—C33	120.6 (2)
C41—N6—C42	110.47 (17)	C27—C28—C29	120.7 (3)
C41—N6—H6	124.8	C27—C28—H28	119.7
C42—N6—H6	124.8	C29—C28—H28	119.7
C11—O1—C25	117.96 (17)	C30—C29—C28	120.6 (3)
C13—O2—C26	117.78 (17)	C30—C29—H29	119.7
C37—O3—C51	117.87 (17)	C28—C29—H29	119.7
C39—O4—C52	117.16 (17)	C29—C30—C31	119.5 (3)
C6—C1—C2	118.3 (2)	C29—C30—H30	120.2
C6—C1—C7	121.1 (2)	C31—C30—H30	120.2
C2—C1—C7	120.5 (2)	C30—C31—C32	119.9 (2)
C3—C2—C1	120.9 (2)	C30—C31—H31	120.0
C3—C2—H2	119.6	C32—C31—H31	120.0
C1—C2—H2	119.6	C31—C32—C27	121.0 (2)
C2—C3—C4	119.6 (3)	C31—C32—H32	119.5
C2—C3—H3A	120.2	C27—C32—H32	119.5
C4—C3—H3A	120.2	C27—C33—S3	106.50 (15)
C5—C4—C3	120.4 (2)	C27—C33—H33A	110.4
C5—C4—H4A	119.8	S3—C33—H33A	110.4
C3—C4—H4A	119.8	C27—C33—H33B	110.4
C4—C5—C6	119.8 (2)	S3—C33—H33B	110.4
C4—C5—H5	120.1	H33A—C33—H33B	108.6
C6—C5—H5	120.1	N4—C34—S4	123.02 (17)
C1—C6—C5	121.0 (2)	N4—C34—S3	112.47 (16)
C1—C6—H6A	119.5	S4—C34—S3	124.51 (14)
C5—C6—H6A	119.5	C37—C35—C41	115.23 (19)
C1—C7—S1	106.11 (15)	C37—C35—C36	121.77 (19)
C1—C7—H7A	110.5	C41—C35—C36	123.0 (2)
S1—C7—H7A	110.5	N5—C36—C35	119.0 (2)
C1—C7—H7B	110.5	N5—C36—H36	120.5
S1—C7—H7B	110.5	C35—C36—H36	120.5
H7A—C7—H7B	108.7	O3—C37—C38	122.4 (2)
N1—C8—S2	122.94 (16)	O3—C37—C35	115.52 (19)
N1—C8—S1	112.08 (15)	C38—C37—C35	122.1 (2)
S2—C8—S1	124.97 (13)	C39—C38—C37	120.6 (2)
N2—C9—C10	119.78 (19)	C39—C38—H38	119.7
N2—C9—H9	120.1	C37—C38—H38	119.7
C10—C9—H9	120.1	O4—C39—C38	122.33 (19)
C11—C10—C15	115.09 (19)	O4—C39—C40	117.33 (18)
C11—C10—C9	121.99 (19)	C38—C39—C40	120.34 (19)
C15—C10—C9	122.76 (19)	C39—C40—C41	117.10 (19)
O1—C11—C12	121.99 (19)	C39—C40—C44	135.86 (19)
O1—C11—C10	115.42 (18)	C41—C40—C44	107.02 (18)
C12—C11—C10	122.6 (2)	N6—C41—C40	107.34 (18)
C13—C12—C11	120.5 (2)	N6—C41—C35	128.02 (19)
C13—C12—H12	119.8	C40—C41—C35	124.64 (19)
C11—C12—H12	119.8	C44—C42—N6	108.84 (19)
O2—C13—C12	122.81 (19)	C44—C42—C43	132.2 (2)
O2—C13—C14	117.04 (19)	N6—C42—C43	118.92 (18)
C12—C13—C14	120.16 (19)	C42—C43—H43A	109.5
C13—C14—C15	117.29 (19)	C42—C43—H43B	109.5
C13—C14—C18	135.7 (2)	H43A—C43—H43B	109.5
C15—C14—C18	106.84 (18)	C42—C43—H43C	109.5
N3—C15—C14	107.63 (18)	H43A—C43—H43C	109.5
N3—C15—C10	127.87 (19)	H43B—C43—H43C	109.5
C14—C15—C10	124.39 (19)	C42—C44—C40	106.34 (18)
C18—C16—N3	109.44 (18)	C42—C44—C45	125.6 (2)
C18—C16—C17	131.52 (19)	C40—C44—C45	127.95 (19)
N3—C16—C17	119.00 (18)	C46—C45—C50	117.4 (2)
C16—C17—H17A	109.5	C46—C45—C44	122.1 (2)
C16—C17—H17B	109.5	C50—C45—C44	120.6 (2)
H17A—C17—H17B	109.5	C47—C46—C45	121.3 (2)
C16—C17—H17C	109.5	C47—C46—H46	119.3
H17A—C17—H17C	109.5	C45—C46—H46	119.3
H17B—C17—H17C	109.5	C48—C47—C46	120.7 (2)
C16—C18—C14	105.94 (18)	C48—C47—H47	119.7
C16—C18—C19	124.81 (19)	C46—C47—H47	119.7
C14—C18—C19	129.0 (2)	C47—C48—C49	119.1 (2)
C24—C19—C20	118.1 (2)	C47—C48—H48	120.4
C24—C19—C18	122.2 (2)	C49—C48—H48	120.4
C20—C19—C18	119.7 (2)	C50—C49—C48	120.3 (2)
C21—C20—C19	120.7 (2)	C50—C49—H49	119.9
C21—C20—H20	119.6	C48—C49—H49	119.9
C19—C20—H20	119.6	C49—C50—C45	121.2 (2)
C22—C21—C20	120.2 (2)	C49—C50—H50	119.4
C22—C21—H21	119.9	C45—C50—H50	119.4
C20—C21—H21	119.9	O3—C51—H51A	109.5
C23—C22—C21	119.3 (2)	O3—C51—H51B	109.5
C23—C22—H22	120.3	H51A—C51—H51B	109.5
C21—C22—H22	120.3	O3—C51—H51C	109.5
C24—C23—C22	120.6 (2)	H51A—C51—H51C	109.5
C24—C23—H23	119.7	H51B—C51—H51C	109.5
C22—C23—H23	119.7	O4—C52—H52A	109.5
C23—C24—C19	121.0 (2)	O4—C52—H52B	109.5
C23—C24—H24	119.5	H52A—C52—H52B	109.5
C19—C24—H24	119.5	O4—C52—H52C	109.5
O1—C25—H25A	109.5	H52A—C52—H52C	109.5
O1—C25—H25B	109.5	H52B—C52—H52C	109.5

C8—N1—N2—C9	−173.9 (2)	C18—C19—C24—C23	178.9 (2)
C34—N4—N5—C36	173.4 (2)	C32—C27—C28—C29	1.6 (5)
C6—C1—C2—C3	0.3 (4)	C33—C27—C28—C29	−178.7 (3)
C7—C1—C2—C3	179.5 (2)	C27—C28—C29—C30	0.1 (5)
C1—C2—C3—C4	0.8 (4)	C28—C29—C30—C31	−2.0 (5)
C2—C3—C4—C5	−1.3 (4)	C29—C30—C31—C32	2.1 (4)
C3—C4—C5—C6	0.6 (4)	C30—C31—C32—C27	−0.3 (4)
C2—C1—C6—C5	−1.0 (4)	C28—C27—C32—C31	−1.5 (4)
C7—C1—C6—C5	179.8 (2)	C33—C27—C32—C31	178.8 (2)
C4—C5—C6—C1	0.5 (4)	C28—C27—C33—S3	83.8 (3)
C6—C1—C7—S1	120.9 (2)	C32—C27—C33—S3	−96.5 (2)
C2—C1—C7—S1	−58.3 (3)	C34—S3—C33—C27	−179.61 (16)
C8—S1—C7—C1	−177.53 (16)	N5—N4—C34—S4	175.72 (15)
N2—N1—C8—S2	−175.46 (15)	N5—N4—C34—S3	−4.9 (3)
N2—N1—C8—S1	5.2 (2)	C33—S3—C34—N4	179.96 (17)
C7—S1—C8—N1	−177.14 (16)	C33—S3—C34—S4	−0.65 (18)
C7—S1—C8—S2	3.54 (18)	N4—N5—C36—C35	176.60 (18)
N1—N2—C9—C10	−174.83 (18)	C37—C35—C36—N5	−179.6 (2)
N2—C9—C10—C11	177.1 (2)	C41—C35—C36—N5	−1.9 (3)
N2—C9—C10—C15	1.9 (3)	C51—O3—C37—C38	3.2 (3)
C25—O1—C11—C12	1.6 (3)	C51—O3—C37—C35	−176.68 (19)
C25—O1—C11—C10	−178.21 (19)	C41—C35—C37—O3	−179.32 (18)
C15—C10—C11—O1	−179.30 (18)	C36—C35—C37—O3	−1.4 (3)
C9—C10—C11—O1	5.1 (3)	C41—C35—C37—C38	0.8 (3)
C15—C10—C11—C12	0.8 (3)	C36—C35—C37—C38	178.7 (2)
C9—C10—C11—C12	−174.7 (2)	O3—C37—C38—C39	179.2 (2)
O1—C11—C12—C13	180.0 (2)	C35—C37—C38—C39	−0.9 (3)
C10—C11—C12—C13	−0.2 (3)	C52—O4—C39—C38	0.8 (3)
C26—O2—C13—C12	−2.0 (3)	C52—O4—C39—C40	−178.75 (18)
C26—O2—C13—C14	177.40 (18)	C37—C38—C39—O4	179.69 (19)
C11—C12—C13—O2	179.58 (19)	C37—C38—C39—C40	−0.7 (3)
C11—C12—C13—C14	0.2 (3)	O4—C39—C40—C41	−178.01 (18)
O2—C13—C14—C15	179.65 (18)	C38—C39—C40—C41	2.4 (3)
C12—C13—C14—C15	−0.9 (3)	O4—C39—C40—C44	−0.3 (4)
O2—C13—C14—C18	−5.7 (4)	C38—C39—C40—C44	−179.9 (2)
C12—C13—C14—C18	173.8 (2)	C42—N6—C41—C40	0.5 (2)
C16—N3—C15—C14	−1.9 (2)	C42—N6—C41—C35	−179.0 (2)
C16—N3—C15—C10	174.5 (2)	C39—C40—C41—N6	177.86 (18)
C13—C14—C15—N3	178.33 (18)	C44—C40—C41—N6	−0.5 (2)
C18—C14—C15—N3	2.2 (2)	C39—C40—C41—C35	−2.6 (3)
C13—C14—C15—C10	1.7 (3)	C44—C40—C41—C35	179.0 (2)
C18—C14—C15—C10	−174.39 (19)	C37—C35—C41—N6	−179.6 (2)
C11—C10—C15—N3	−177.6 (2)	C36—C35—C41—N6	2.6 (3)
C9—C10—C15—N3	−2.0 (3)	C37—C35—C41—C40	1.1 (3)
C11—C10—C15—C14	−1.7 (3)	C36—C35—C41—C40	−176.8 (2)
C9—C10—C15—C14	173.9 (2)	C41—N6—C42—C44	−0.3 (2)
C15—N3—C16—C18	0.9 (2)	C41—N6—C42—C43	178.61 (19)
C15—N3—C16—C17	178.78 (19)	N6—C42—C44—C40	0.0 (2)
N3—C16—C18—C14	0.5 (2)	C43—C42—C44—C40	−178.7 (2)
C17—C16—C18—C14	−177.0 (2)	N6—C42—C44—C45	176.58 (19)
N3—C16—C18—C19	−174.34 (19)	C43—C42—C44—C45	−2.1 (4)
C17—C16—C18—C19	8.1 (4)	C39—C40—C44—C42	−177.6 (2)
C13—C14—C18—C16	−176.7 (2)	C41—C40—C44—C42	0.3 (2)
C15—C14—C18—C16	−1.7 (2)	C39—C40—C44—C45	5.9 (4)
C13—C14—C18—C19	−2.1 (4)	C41—C40—C44—C45	−176.2 (2)
C15—C14—C18—C19	172.9 (2)	C42—C44—C45—C46	48.5 (3)
C16—C18—C19—C24	−133.1 (2)	C40—C44—C45—C46	−135.6 (2)
C14—C18—C19—C24	53.3 (3)	C42—C44—C45—C50	−129.9 (2)
C16—C18—C19—C20	46.6 (3)	C40—C44—C45—C50	46.0 (3)
C14—C18—C19—C20	−127.0 (2)	C50—C45—C46—C47	0.3 (4)
C24—C19—C20—C21	0.1 (3)	C44—C45—C46—C47	−178.2 (2)
C18—C19—C20—C21	−179.6 (2)	C45—C46—C47—C48	−0.4 (4)
C19—C20—C21—C22	0.7 (4)	C46—C47—C48—C49	0.0 (4)
C20—C21—C22—C23	−0.8 (4)	C47—C48—C49—C50	0.5 (4)
C21—C22—C23—C24	0.1 (4)	C48—C49—C50—C45	−0.6 (4)
C22—C23—C24—C19	0.8 (3)	C46—C45—C50—C49	0.3 (3)
C20—C19—C24—C23	−0.9 (3)	C44—C45—C50—C49	178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S4	0.88	2.47	3.330 (2)	164
N4—H4···S2	0.88	2.50	3.368 (2)	170

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅N₃O₂S₂
M_r	475.61
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.0913 (2), 12.8541 (3), 18.9232 (4)
α, β, γ (°)	90.461 (1), 103.960 (1), 93.944 (1)
V (Å³)	2375.71 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.40 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.906, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	22819, 10887, 7429
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.01
No. of reflections	10887
No. of parameters	601
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S4	0.88	2.47	3.330 (2)	164
N4—H4···S2	0.88	2.50	3.368 (2)	170

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1788. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jones, A. W., Wahyuningsih, T. W., Pchalek, K., Kumar, N. & Black, D. S. C. (2005). Tetrahedron, 61. 10490–10500. Google Scholar
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2430. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). 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
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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Volume 64| Part 12| December 2008| Page o2442

doi:10.1107/S1600536808038592

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

Benzyl N′-(4,6-dimeth­­oxy-2-methyl-3-phenyl-1H-indol-7-ylmethyl­ene)hydrazinecarbodi­thio­ate

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Experimental

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Refinement

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Acknowledgements

References

organic compounds

Benzyl N′-(4,6-dimethoxy-2-methyl-3-phenyl-1H-indol-7-ylmethylene)hydrazinecarbodithioate