{2-[(2-Bromo-5-meth­oxy­benzyl­idene)amino]-4,5,6,7-tetra­hydro­benzo[b]thiophen-3-yl}(phen­yl)methanone

Kaur, M.; Jasinski, J.P.; Yamuna, T.S.; Yathirajan, H.S.; Byrappa, K.

doi:10.1107/S1600536814008290

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o581-o582

doi:10.1107/S1600536814008290

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{2-[(2-Bromo-5-methoxybenzylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}(phenyl)methanone

Manpreet Kaur,^a Jerry P. Jasinski,^b ^* Thammarse S. Yamuna,^a H. S. Yathirajan ^a and K. Byrappa ^c

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cMaterials Science Center, University of Mysore, Vijyana Bhavan Building, Manasagangothri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 3 April 2014; accepted 12 April 2014; online 18 April 2014)

In the title compound, C₂₃H₂₀BrNO₂S, disorder was modeled for the outer two C atoms of the cyclohexene ring over two sets of sites with an occupancy ratio of 0.580 (11):0.420 (11). Both rings have a half-chair conformation. The dihedral angles between the mean plane of the thiophene ring and the benzene and phenyl rings are 9.2 (2) and 66.1 (2)°, respectively. The benzene and phenyl rings are inclined to each other by 74.8 (8)°. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers.

CCDC reference: 997010

Related literature

For applications of 2-aminothiophene derivatives, see: Sabnis et al. (1999 ); Puterová et al. (2010 ). For the biological and industrial importance of Schiff bases, see: Desai et al. (2001 ); Karia & Parsania (1999 ); Samadhiya & Halve (2001 ); Singh & Dash (1988 ); Aydogan et al. (2001 ); Taggi et al. (2002 ). For a related structure, see: Kubicki et al. (2012 ). For puckering parameters, see: Cremer & Pople (1975 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₂₀BrNO₂S
M_r = 454.37
Monoclinic, P 2₁ /n
a = 8.84813 (17) Å
b = 12.5563 (2) Å
c = 18.4384 (4) Å
β = 102.363 (2)°
V = 2001.00 (7) Å³
Z = 4
Cu Kα radiation
μ = 3.92 mm⁻¹
T = 173 K
0.26 × 0.22 × 0.14 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.725, T_max = 1.000
12404 measured reflections
3853 independent reflections
3440 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.087
S = 1.05
3853 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.95	2.58	3.294 (3)	132
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ) and PLATON.

Supporting information

CCDC reference: 997010

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814008290/su2721sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008290/su2721Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008290/su2721Isup3.cml

checkCIF report

Comment top

2-Aminothiophene derivatives have been used in a number of applications in pesticides, dyes and pharmaceuticals (Sabnis et al. 1999; Puterová et al. 2010). Schiff base compounds show biological activities including antibacterial, antifungal, anticancer and herbicidal activities (Desai et al., 2001; Karia & Parsania, 1999; Samadhiya & Halve, 2001; Singh & Dash, 1988) and have been used as starting materials in the synthesis of compounds of industrial (Aydogan et al., 2001) and biological interest such as β-lactams (Taggi et al., 2002). In continuation of our work on the Schiff base derivatives of 2-aminothiophenes (Kubicki et al., 2012), we report herein on the crystal structure of the title compound.

In the title compound, Fig. 1, disorder was modeled for atoms C5 and C6 of the cyclohexene ring over two sites (A and B) with an occupancy ratio of 0.580 (11):0.420 (11). Both rings have half-chair conformations with puckering parameters (Cremer & Pople, 1975) Q,θ, and ϕ being = 0.520 (6) Å, 49.9 (4) ° and 154.8 (6) °, respectively, for ring A and being = 0.527 (8) Å, 130.1 (5) ° and 322.0 (7) °, respectively, for ring B. The dihedral angles between the mean plane of the thiophene ring and the benzene and phenyl rings are 9.2 (2) ° and 66.1 (2) °, respectively. The benzene and phenyl rings are twisted with respect to each other by 74.8 (8)°. Bond lengths are in normal ranges (Allen et al., 1987).

In the crystal, molecules are linked by pairs of C-H···O hydrogen bonds forming inversion dimers (Table 1 and Fig. 2).

Related literature top

For applications of 2-aminothiophene derivatives, see: Sabnis et al. (1999); Puterová et al. (2010). For the biological and industrial importance of Schiff bases, see: Desai et al. (2001); Karia & Parsania (1999); Samadhiya & Halve (2001); Singh & Dash (1988); Aydogan et al. (2001); Taggi et al. (2002). For a related structure, see: Kubicki et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a solution of (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)- phenyl-methanone (200 mg, 0.79 mmol) in 10 ml of methanol an equimolar amount of 2-bromo-5-methoxybenzaldehyde (170 mg, 0.79 mmol) was added with constant stirring. The mixture was then refluxed for 6 hours and a yellow precipitate was obtained. The reaction completion was confirmed by thin layer chromatography. The precipitate was filtered and dried at room temperature overnight. Slow evaporation of a solution in CH₂Cl₂ gave yellow block-like crystals of the title compound.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level (the minor component atoms C5B and C6B are not shown).
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The C—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity; the minor component atoms C5B and C6B are not shown).

{2-[(2-Bromo-5-methoxybenzylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}(phenyl)methanone top

Crystal data top

C₂₃H₂₀BrNO₂S	F(000) = 928
M_r = 454.37	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 8.84813 (17) Å	Cell parameters from 5917 reflections
b = 12.5563 (2) Å	θ = 4.3–71.4°
c = 18.4384 (4) Å	µ = 3.92 mm⁻¹
β = 102.363 (2)°	T = 173 K
V = 2001.00 (7) Å³	Irregular, yellow
Z = 4	0.26 × 0.22 × 0.14 mm

Data collection top

Agilent Eos Gemini diffractometer	3440 reflections with I > 2σ(I)
Radiation source: Enhance (Cu) X-ray Source	R_int = 0.034
ω scans	θ_max = 71.3°, θ_min = 4.3°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −10→10
T_min = 0.725, T_max = 1.000	k = −15→13
12404 measured reflections	l = −22→22
3853 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0539P)² + 0.1502P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3853 reflections	Δρ_max = 0.56 e Å⁻³
273 parameters	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₃H₂₀BrNO₂S	V = 2001.00 (7) Å³
M_r = 454.37	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 8.84813 (17) Å	µ = 3.92 mm⁻¹
b = 12.5563 (2) Å	T = 173 K
c = 18.4384 (4) Å	0.26 × 0.22 × 0.14 mm
β = 102.363 (2)°

Data collection top

Agilent Eos Gemini diffractometer	3853 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	3440 reflections with I > 2σ(I)
T_min = 0.725, T_max = 1.000	R_int = 0.034
12404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.05	Δρ_max = 0.56 e Å⁻³
3853 reflections	Δρ_min = −0.31 e Å⁻³
273 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	Occ. (<1)
Br1	0.09686 (3)	0.02458 (2)	0.60828 (2)	0.03755 (10)
S1	0.37522 (6)	−0.13254 (4)	0.41239 (3)	0.02972 (12)
O1	0.3841 (2)	0.10568 (12)	0.20797 (8)	0.0407 (4)
O2	0.17717 (19)	0.45920 (12)	0.48309 (10)	0.0405 (4)
N1	0.31360 (18)	0.08489 (13)	0.41394 (9)	0.0273 (3)
C1	0.4306 (2)	0.10714 (15)	0.27533 (11)	0.0277 (4)
C2	0.4297 (2)	0.00672 (15)	0.31824 (11)	0.0252 (4)
C3	0.4776 (2)	−0.09409 (15)	0.29439 (10)	0.0260 (4)
C4	0.5456 (2)	−0.11311 (16)	0.22707 (12)	0.0326 (4)
H4AA	0.4632	−0.1074	0.1815	0.039*	0.580 (11)
H4AB	0.6246	−0.0581	0.2247	0.039*	0.580 (11)
H4BC	0.6560	−0.0922	0.2382	0.039*	0.420 (11)
H4BD	0.4906	−0.0689	0.1852	0.039*	0.420 (11)
C5A	0.6185 (8)	−0.2219 (3)	0.2307 (3)	0.0388 (14)	0.580 (11)
H5AA	0.7174	−0.2213	0.2680	0.047*	0.580 (11)
H5AB	0.6418	−0.2394	0.1819	0.047*	0.580 (11)
C6A	0.5129 (10)	−0.3069 (3)	0.2513 (3)	0.0427 (14)	0.580 (11)
H6AA	0.5568	−0.3783	0.2462	0.051*	0.580 (11)
H6AB	0.4100	−0.3028	0.2173	0.051*	0.580 (11)
C5B	0.5303 (11)	−0.2343 (5)	0.2047 (4)	0.0386 (18)	0.420 (11)
H5BA	0.4198	−0.2524	0.1865	0.046*	0.420 (11)
H5BB	0.5848	−0.2476	0.1639	0.046*	0.420 (11)
C6B	0.5977 (12)	−0.3033 (5)	0.2695 (4)	0.0411 (17)	0.420 (11)
H6BA	0.7060	−0.2820	0.2904	0.049*	0.420 (11)
H6BB	0.5974	−0.3786	0.2536	0.049*	0.420 (11)
C7	0.4959 (3)	−0.29043 (15)	0.33123 (12)	0.0353 (4)
H7AA	0.4128	−0.3367	0.3419	0.042*	0.580 (11)
H7AB	0.5938	−0.3089	0.3662	0.042*	0.580 (11)
H7BC	0.3994	−0.3322	0.3165	0.042*	0.420 (11)
H7BD	0.5543	−0.3186	0.3793	0.042*	0.420 (11)
C8	0.4568 (2)	−0.17526 (15)	0.34010 (11)	0.0269 (4)
C9	0.3723 (2)	−0.00049 (15)	0.38167 (11)	0.0255 (4)
C10	0.4899 (2)	0.20856 (15)	0.31299 (10)	0.0267 (4)
C11	0.5983 (2)	0.20984 (17)	0.38015 (12)	0.0346 (4)
H11	0.6293	0.1451	0.4057	0.041*
C12	0.6606 (3)	0.3059 (2)	0.40951 (14)	0.0441 (5)
H12	0.7362	0.3069	0.4547	0.053*
C13	0.6125 (3)	0.40071 (19)	0.37281 (15)	0.0483 (6)
H13	0.6558	0.4664	0.3928	0.058*
C14	0.5021 (3)	0.39969 (18)	0.30749 (14)	0.0444 (5)
H14	0.4674	0.4647	0.2832	0.053*
C15	0.4416 (3)	0.30354 (16)	0.27719 (12)	0.0345 (4)
H15	0.3668	0.3029	0.2318	0.041*
C16	0.2623 (2)	0.07449 (15)	0.47319 (11)	0.0277 (4)
H16	0.2647	0.0067	0.4964	0.033*
C17	0.1995 (2)	0.16678 (16)	0.50565 (11)	0.0281 (4)
C18	0.1202 (2)	0.15806 (16)	0.56306 (11)	0.0299 (4)
C19	0.0562 (2)	0.24697 (18)	0.58977 (12)	0.0348 (4)
H19	−0.0009	0.2392	0.6276	0.042*
C20	0.0754 (2)	0.34625 (17)	0.56152 (12)	0.0358 (5)
H20	0.0319	0.4071	0.5799	0.043*
C21	0.1592 (2)	0.35725 (16)	0.50552 (12)	0.0319 (4)
C22	0.2189 (2)	0.26847 (16)	0.47765 (11)	0.0299 (4)
H22	0.2739	0.2763	0.4390	0.036*
C23	0.2887 (3)	0.47572 (17)	0.43904 (14)	0.0413 (5)
H23A	0.2536	0.4414	0.3906	0.062*
H23B	0.3879	0.4449	0.4642	0.062*
H23C	0.3015	0.5523	0.4320	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04351 (15)	0.03807 (15)	0.03571 (15)	−0.00469 (8)	0.01879 (10)	0.00195 (8)
S1	0.0388 (3)	0.0250 (2)	0.0288 (2)	−0.00344 (17)	0.0148 (2)	0.00060 (17)
O1	0.0647 (10)	0.0314 (7)	0.0247 (7)	0.0017 (7)	0.0063 (7)	−0.0007 (6)
O2	0.0448 (9)	0.0312 (7)	0.0485 (9)	0.0077 (6)	0.0168 (7)	0.0049 (7)
N1	0.0286 (8)	0.0273 (8)	0.0282 (8)	−0.0024 (6)	0.0107 (6)	−0.0035 (6)
C1	0.0306 (9)	0.0271 (9)	0.0278 (10)	0.0021 (7)	0.0116 (7)	0.0006 (7)
C2	0.0252 (9)	0.0253 (9)	0.0259 (9)	−0.0015 (7)	0.0075 (7)	−0.0021 (7)
C3	0.0256 (8)	0.0259 (9)	0.0270 (9)	−0.0015 (7)	0.0070 (7)	−0.0027 (7)
C4	0.0370 (10)	0.0313 (10)	0.0336 (11)	0.0019 (8)	0.0167 (8)	−0.0013 (8)
C5A	0.046 (3)	0.031 (2)	0.046 (3)	0.0047 (19)	0.027 (3)	−0.0045 (17)
C6A	0.058 (4)	0.028 (2)	0.051 (3)	−0.003 (2)	0.030 (3)	−0.0095 (18)
C5B	0.044 (4)	0.038 (3)	0.037 (3)	−0.001 (3)	0.016 (3)	−0.010 (2)
C6B	0.047 (4)	0.033 (3)	0.047 (4)	0.005 (3)	0.017 (3)	−0.011 (2)
C7	0.0453 (11)	0.0235 (10)	0.0386 (11)	−0.0014 (8)	0.0125 (9)	−0.0031 (8)
C8	0.0262 (9)	0.0260 (9)	0.0291 (10)	−0.0018 (7)	0.0073 (7)	−0.0033 (7)
C9	0.0272 (9)	0.0231 (8)	0.0278 (9)	−0.0023 (7)	0.0092 (7)	0.0002 (7)
C10	0.0308 (9)	0.0267 (9)	0.0267 (9)	−0.0021 (7)	0.0154 (7)	−0.0011 (7)
C11	0.0352 (10)	0.0351 (11)	0.0354 (11)	−0.0033 (8)	0.0119 (8)	−0.0009 (8)
C12	0.0424 (12)	0.0498 (14)	0.0425 (13)	−0.0135 (10)	0.0144 (10)	−0.0113 (10)
C13	0.0623 (15)	0.0338 (12)	0.0562 (15)	−0.0214 (11)	0.0295 (12)	−0.0137 (11)
C14	0.0671 (15)	0.0253 (10)	0.0479 (13)	−0.0045 (10)	0.0279 (12)	0.0012 (9)
C15	0.0463 (12)	0.0289 (10)	0.0323 (11)	−0.0002 (8)	0.0169 (9)	0.0023 (8)
C16	0.0282 (9)	0.0281 (9)	0.0279 (9)	−0.0009 (7)	0.0086 (7)	−0.0006 (7)
C17	0.0256 (9)	0.0311 (10)	0.0288 (10)	0.0003 (7)	0.0085 (7)	−0.0031 (8)
C18	0.0289 (9)	0.0342 (10)	0.0286 (10)	−0.0008 (7)	0.0107 (8)	0.0012 (8)
C19	0.0290 (9)	0.0471 (12)	0.0318 (10)	0.0034 (8)	0.0140 (8)	−0.0043 (9)
C20	0.0329 (10)	0.0377 (11)	0.0387 (11)	0.0095 (8)	0.0123 (9)	−0.0047 (9)
C21	0.0297 (9)	0.0304 (10)	0.0352 (11)	0.0042 (7)	0.0061 (8)	0.0004 (8)
C22	0.0291 (9)	0.0356 (10)	0.0270 (9)	0.0015 (7)	0.0105 (8)	−0.0007 (8)
C23	0.0443 (12)	0.0361 (12)	0.0447 (13)	−0.0001 (9)	0.0121 (10)	0.0061 (9)

Geometric parameters (Å, º) top

Br1—C18	1.903 (2)	C6B—C7	1.603 (7)
S1—C8	1.7314 (19)	C7—H7AA	0.9900
S1—C9	1.7506 (19)	C7—H7AB	0.9900
O1—C1	1.222 (2)	C7—H7BC	0.9900
O2—C21	1.365 (3)	C7—H7BD	0.9900
O2—C23	1.421 (3)	C7—C8	1.504 (3)
N1—C9	1.380 (3)	C10—C11	1.395 (3)
N1—C16	1.277 (2)	C10—C15	1.386 (3)
C1—C2	1.489 (3)	C11—H11	0.9500
C1—C10	1.491 (3)	C11—C12	1.387 (3)
C2—C3	1.433 (3)	C12—H12	0.9500
C2—C9	1.374 (3)	C12—C13	1.391 (4)
C3—C4	1.510 (3)	C13—H13	0.9500
C3—C8	1.360 (3)	C13—C14	1.379 (4)
C4—H4AA	0.9900	C14—H14	0.9500
C4—H4AB	0.9900	C14—C15	1.389 (3)
C4—H4BC	0.9900	C15—H15	0.9500
C4—H4BD	0.9900	C16—H16	0.9500
C4—C5A	1.506 (4)	C16—C17	1.467 (3)
C4—C5B	1.575 (6)	C17—C18	1.394 (3)
C5A—H5AA	0.9900	C17—C22	1.402 (3)
C5A—H5AB	0.9900	C18—C19	1.389 (3)
C5A—C6A	1.519 (8)	C19—H19	0.9500
C6A—H6AA	0.9900	C19—C20	1.375 (3)
C6A—H6AB	0.9900	C20—H20	0.9500
C6A—C7	1.526 (5)	C20—C21	1.401 (3)
C5B—H5BA	0.9900	C21—C22	1.379 (3)
C5B—H5BB	0.9900	C22—H22	0.9500
C5B—C6B	1.494 (12)	C23—H23A	0.9800
C6B—H6BA	0.9900	C23—H23B	0.9800
C6B—H6BB	0.9900	C23—H23C	0.9800

C8—S1—C9	91.38 (9)	C8—C7—H7AA	110.1
C21—O2—C23	116.75 (16)	C8—C7—H7AB	110.1
C16—N1—C9	121.68 (17)	C8—C7—H7BC	109.5
O1—C1—C2	119.22 (18)	C8—C7—H7BD	109.5
O1—C1—C10	119.64 (18)	C3—C8—S1	112.26 (14)
C2—C1—C10	121.13 (17)	C3—C8—C7	126.05 (18)
C3—C2—C1	123.31 (17)	C7—C8—S1	121.68 (15)
C9—C2—C1	123.55 (17)	N1—C9—S1	125.24 (14)
C9—C2—C3	112.97 (17)	C2—C9—S1	110.80 (15)
C2—C3—C4	126.00 (17)	C2—C9—N1	123.88 (18)
C8—C3—C2	112.57 (17)	C11—C10—C1	122.00 (18)
C8—C3—C4	121.43 (17)	C15—C10—C1	118.12 (18)
C3—C4—H4AA	109.6	C15—C10—C11	119.77 (19)
C3—C4—H4AB	109.6	C10—C11—H11	120.1
C3—C4—H4BC	109.7	C12—C11—C10	119.8 (2)
C3—C4—H4BD	109.7	C12—C11—H11	120.1
C3—C4—C5B	110.0 (3)	C11—C12—H12	120.0
H4AA—C4—H4AB	108.1	C11—C12—C13	120.0 (2)
H4BC—C4—H4BD	108.2	C13—C12—H12	120.0
C5A—C4—C3	110.4 (2)	C12—C13—H13	119.9
C5A—C4—H4AA	109.6	C14—C13—C12	120.2 (2)
C5A—C4—H4AB	109.6	C14—C13—H13	119.9
C5B—C4—H4BC	109.7	C13—C14—H14	120.0
C5B—C4—H4BD	109.7	C13—C14—C15	120.0 (2)
C4—C5A—H5AA	109.3	C15—C14—H14	120.0
C4—C5A—H5AB	109.3	C10—C15—C14	120.2 (2)
C4—C5A—C6A	111.6 (5)	C10—C15—H15	119.9
H5AA—C5A—H5AB	108.0	C14—C15—H15	119.9
C6A—C5A—H5AA	109.3	N1—C16—H16	119.9
C6A—C5A—H5AB	109.3	N1—C16—C17	120.24 (18)
C5A—C6A—H6AA	109.7	C17—C16—H16	119.9
C5A—C6A—H6AB	109.7	C18—C17—C16	122.95 (18)
C5A—C6A—C7	109.8 (5)	C18—C17—C22	118.20 (18)
H6AA—C6A—H6AB	108.2	C22—C17—C16	118.85 (17)
C7—C6A—H6AA	109.7	C17—C18—Br1	121.43 (15)
C7—C6A—H6AB	109.7	C19—C18—Br1	117.50 (15)
C4—C5B—H5BA	109.5	C19—C18—C17	121.06 (19)
C4—C5B—H5BB	109.5	C18—C19—H19	120.0
H5BA—C5B—H5BB	108.1	C20—C19—C18	120.08 (19)
C6B—C5B—C4	110.7 (6)	C20—C19—H19	120.0
C6B—C5B—H5BA	109.5	C19—C20—H20	120.1
C6B—C5B—H5BB	109.5	C19—C20—C21	119.75 (19)
C5B—C6B—H6BA	109.9	C21—C20—H20	120.1
C5B—C6B—H6BB	109.9	O2—C21—C20	115.47 (18)
C5B—C6B—C7	108.8 (6)	O2—C21—C22	124.50 (19)
H6BA—C6B—H6BB	108.3	C22—C21—C20	120.02 (19)
C7—C6B—H6BA	109.9	C17—C22—H22	119.6
C7—C6B—H6BB	109.9	C21—C22—C17	120.81 (18)
C6A—C7—H7AA	110.1	C21—C22—H22	119.6
C6A—C7—H7AB	110.1	O2—C23—H23A	109.5
C6B—C7—H7BC	109.5	O2—C23—H23B	109.5
C6B—C7—H7BD	109.5	O2—C23—H23C	109.5
H7AA—C7—H7AB	108.4	H23A—C23—H23B	109.5
H7BC—C7—H7BD	108.1	H23A—C23—H23C	109.5
C8—C7—C6A	107.9 (2)	H23B—C23—H23C	109.5
C8—C7—C6B	110.6 (3)

Br1—C18—C19—C20	177.08 (17)	C5B—C6B—C7—C8	−43.3 (8)
O1—C1—C2—C3	42.7 (3)	C6B—C7—C8—S1	−169.4 (4)
O1—C1—C2—C9	−132.2 (2)	C6B—C7—C8—C3	11.4 (5)
O1—C1—C10—C11	−153.30 (19)	C8—S1—C9—N1	177.94 (17)
O1—C1—C10—C15	22.8 (3)	C8—S1—C9—C2	0.96 (15)
O2—C21—C22—C17	177.79 (19)	C8—C3—C4—C5A	−13.9 (4)
N1—C16—C17—C18	169.70 (19)	C8—C3—C4—C5B	19.7 (5)
N1—C16—C17—C22	−9.9 (3)	C9—S1—C8—C3	−1.23 (15)
C1—C2—C3—C4	4.7 (3)	C9—S1—C8—C7	179.49 (17)
C1—C2—C3—C8	−175.86 (17)	C9—N1—C16—C17	−179.50 (17)
C1—C2—C9—S1	174.92 (15)	C9—C2—C3—C4	−179.91 (18)
C1—C2—C9—N1	−2.1 (3)	C9—C2—C3—C8	−0.4 (2)
C1—C10—C11—C12	174.01 (19)	C10—C1—C2—C3	−136.11 (19)
C1—C10—C15—C14	−175.38 (19)	C10—C1—C2—C9	48.9 (3)
C2—C1—C10—C11	25.5 (3)	C10—C11—C12—C13	1.4 (3)
C2—C1—C10—C15	−158.38 (18)	C11—C10—C15—C14	0.8 (3)
C2—C3—C4—C5A	165.5 (3)	C11—C12—C13—C14	0.5 (4)
C2—C3—C4—C5B	−160.9 (4)	C12—C13—C14—C15	−1.7 (4)
C2—C3—C8—S1	1.2 (2)	C13—C14—C15—C10	1.1 (3)
C2—C3—C8—C7	−179.59 (18)	C15—C10—C11—C12	−2.0 (3)
C3—C2—C9—S1	−0.5 (2)	C16—N1—C9—S1	3.8 (3)
C3—C2—C9—N1	−177.51 (17)	C16—N1—C9—C2	−179.59 (19)
C3—C4—C5A—C6A	46.7 (7)	C16—C17—C18—Br1	3.6 (3)
C3—C4—C5B—C6B	−53.2 (8)	C16—C17—C18—C19	−176.87 (19)
C4—C3—C8—S1	−179.33 (15)	C16—C17—C22—C21	178.74 (18)
C4—C3—C8—C7	−0.1 (3)	C17—C18—C19—C20	−2.4 (3)
C4—C5A—C6A—C7	−67.6 (8)	C18—C17—C22—C21	−0.9 (3)
C4—C5B—C6B—C7	65.5 (9)	C18—C19—C20—C21	0.2 (3)
C5A—C4—C5B—C6B	43.5 (7)	C19—C20—C21—O2	−177.5 (2)
C5A—C6A—C7—C6B	−51.1 (7)	C19—C20—C21—C22	1.6 (3)
C5A—C6A—C7—C8	49.3 (7)	C20—C21—C22—C17	−1.3 (3)
C6A—C7—C8—S1	161.2 (4)	C22—C17—C18—Br1	−176.77 (14)
C6A—C7—C8—C3	−17.9 (4)	C22—C17—C18—C19	2.7 (3)
C5B—C4—C5A—C6A	−48.4 (6)	C23—O2—C21—C20	166.49 (19)
C5B—C6B—C7—C6A	46.2 (7)	C23—O2—C21—C22	−12.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱ	0.95	2.58	3.294 (3)	132

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱ	0.95	2.58	3.294 (3)	132

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

MK is grateful to the CPEPA–UGC for the award of a Junior Research Fellowship and thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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Volume 70| Part 5| May 2014| Pages o581-o582

doi:10.1107/S1600536814008290

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

{2-[(2-Bromo-5-meth­­oxy­benzyl­­idene)amino]-4,5,6,7-tetra­hydro­benzo[b]thiophen-3-yl}(phen­yl)methanone

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Experimental

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organic compounds

{2-[(2-Bromo-5-methoxybenzylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}(phenyl)methanone