{2-[(4-Nitro­benzyl­idene)amino]-4,5,6,7-tetrahydro-1-benzo­thio­phen-3-yl}(phen­yl)methanone

Kaur, M.; Jasinski, J.P.; Kavitha, C.N.; Yathirajan, H.S.; Byrappa, K.

doi:10.1107/S1600536814012185

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o738-o739

doi:10.1107/S1600536814012185

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{2-[(4-Nitrobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}(phenyl)methanone

Manpreet Kaur,^a Jerry P. Jasinski,^b ^* Channappa N. Kavitha,^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 23 May 2014; accepted 26 May 2014; online 31 May 2014)

In the title compound, C₂₂H₁₈N₂O₃S, disorder is found in the benzoyl group (A and B), as well as for four C atoms of the cyclohexene ring. Two orientations were modeled in a 0.583 (5):0.417 (5) ratio. The cyclohexene ring is in a distorted chair conformation. The dihedral angles between the mean plane of the thiophene ring and the 4-nitrobenzene and phenyl rings are 30.9 (8) and 64.8 (3) (A) and 62.4 (7)° (B). The mean planes of the 4-nitrobenzene and the phenyl rings are almost perpendicular to each other, with dihedral angles of 85.4 (1) (A) and 83.9 (8)° (B). An extensive array of weak C—H⋯O interactions consolidate molecules into a three-dimensional architecture, forming chains along [001] and [010] and layers parallel to (011).

CCDC reference: 1005353

Related literature

For applications of 2-aminothiophene derivatives in pesticides, dyes and pharmaceuticals, see: 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 ). For Schiff bases utilized as starting materials in the synthesis of compounds of industrial and biological interest, see: Aydogan et al. (2001 ); Taggi et al. (2002 ). For related structures, see: Kaur et al. (2014a ,b ); Kubicki et al. (2012 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₂H₁₈N₂O₃S
M_r = 390.44
Monoclinic, P 2₁
a = 4.61595 (13) Å
b = 17.6844 (4) Å
c = 11.7068 (3) Å
β = 91.285 (3)°
V = 955.39 (4) Å³
Z = 2
Cu Kα radiation
μ = 1.72 mm⁻¹
T = 173 K
0.24 × 0.18 × 0.06 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.634, T_max = 1.000
6206 measured reflections
2781 independent reflections
2610 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.02
2781 reflections
263 parameters
138 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack x determined using 764 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons & Flack, 2004 )
Absolute structure parameter: 0.028 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4A—H4AA⋯O1Bⁱ	0.99	2.38	3.15 (4)	135
C4B—H4BA⋯O1Aⁱ	0.99	2.50	3.45 (4)	162
C4B—H4BA⋯O1Bⁱ	0.99	2.26	3.18 (4)	154
C7B—H7BB⋯O2ⁱⁱ	0.99	2.46	3.44 (3)	169
C13B—H13B⋯O3ⁱⁱⁱ	0.95	2.55	3.371 (13)	145
C21—H21⋯O1A^iv	0.95	2.40	3.127 (18)	133
C21—H21⋯O1B^iv	0.95	2.44	3.13 (3)	129
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1; (iii) $[-x-1, y-{\script{1\over 2}}, -z]$ ; (iv) $[-x-1, y+{\script{1\over 2}}, -z+1]$ .

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: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1005353

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814012185/tk5318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814012185/tk5318Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814012185/tk5318Isup3.cml

checkCIF report

Structural commentary top

2-Aminothiophene derivatives have been used in a number of applications, such as in pesticides, dyes and pharmaceuticals. A review on the synthesis and properties of these compounds has been reported (Puterová et al., 2010). Schiff base compounds are an important class of compounds, both synthetically and biologically. These compounds show biological activities including anti-bacterial, anti-fungal, anti-cancer and herbicidal (Desai et al., 2001; Karia & Parsania, 1999; Samadhiya & Halve, 2001; Singh & Dash, 1988). Furthermore, Schiff bases are utilized 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). Some of the recently reported Schiff base structures of 2-aminothiophenes by our group include {2-[(2-hydroxybenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-yl} (phenyl)methanone (Kaur et al., 2014a) and [2-benzylideneamino)-4,5,6,7-tetrahydro benzo[b]thiophene-3-yl](phenyl) methanone (Kaur et al., 2014b). Also, the crystal and molecular structures of two 2-aminothiophenes have been previously reported by our group (Kubicki et al., 2012). In continuation of our work on 2-aminothiophenes and Schiff bases, we report here the crystal structure of the title compound, (I).

In (I), the cyclohexene ring is in a distorted chair conformation with four carbon atoms disordered over two sets of sites with an occupancy ratio of 0.583 (5): 0.417 (5) (Fig. 1). Puckering parameters C3/C4A—C7A/C8: Q and ϕ = 0.511 (4) Å and 157.387 (6)°, and C3/C4B—C7B/C8: Q and ϕ = 0.483 (8) Å and 212.306 (8)° (Cremer & Pople, 1975). The disorder extends to the benzoyl residue (A & B). The dihedral angles between the mean plane of the thiophene ring and the 4-nitrophenyl and the phenyl rings is 30.9 (8) and 64.8 (3) (A) and 62.4 (7)° (B), respectively. The mean planes of 4-nitrophenyl and the phenyl rings are almost perpendicular to each other with a dihedral angle of 85.4 (1) (A) and 83.9 (8)° (B). An extensive array of weak C—H···O intermolecular interactions leads to a 3-D architecure, forming chains along [001] and [010] and layers parallel to (011) (Fig. 2).

Synthesis and crystallization 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 4-nitrobenzaldehyde (120 mg, 0.79 mmol) was added with constant stirring. The mixture was refluxed for 3 h. A yellow precipitate was obtained. Completion of the reaction was confirmed by TLC. The precipitate was filtered and dried at room temperature overnight. The solid was recrystallized using ethylacetate and the crystals were used as such for x-ray diffraction studies.

Refinement top

The H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93 Å (CH) or 0.97 Å (CH₂), and with U_iso set to 1.2U_eq of the parent atom. Disorder was modeled for C4A—C7A and C4B—C7B of the cyclohexane ring, C10A—C15A/O1A and C10B—C15B/O1B of the benzoyl group over two positions with an occupancy ratio of 0.583 (5):0.417 (5).

Related literature top

For applications of 2-aminothiophene derivatives in pesticides, dyes and pharmaceuticals, see: 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). For Schiff bases utilized as starting materials in the synthesis of compounds of industrial and biological interest, see: Aydogan et al. (2001); Taggi et al. (2002). For related structures, see: Kaur et al. (2014a,b); Kubicki et al. (2012). For puckering parameters, see Cremer & Pople (1975).

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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (I) showing the labeling scheme and 30% probability displacement ellipsoids (major and minor components of the disordered atoms in the cyclohexane, benzoyl groups are displayed with dashed lines).
	Fig. 2. Molecular packing for (I) viewed along the b axis. Dashed lines indicate weak C—H···O intermolecular interactions. H atoms not involved in the weak intermolecular interactions have been removed for clarity.

{2-[(4-Nitrobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}(phenyl)methanone top

Crystal data top

C₂₂H₁₈N₂O₃S	F(000) = 408
M_r = 390.44	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 4.61595 (13) Å	Cell parameters from 3146 reflections
b = 17.6844 (4) Å	θ = 4.5–71.4°
c = 11.7068 (3) Å	µ = 1.72 mm⁻¹
β = 91.285 (3)°	T = 173 K
V = 955.39 (4) Å³	Irregular, yellow
Z = 2	0.24 × 0.18 × 0.06 mm

Data collection top

Agilent Eos Gemini diffractometer	2781 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2610 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 71.1°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −5→5
T_min = 0.634, T_max = 1.000	k = −18→21
6206 measured reflections	l = −11→14

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0608P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.21 e Å⁻³
2781 reflections	Δρ_min = −0.19 e Å⁻³
263 parameters	Absolute structure: Flack x determined using 764 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004)
138 restraints	Absolute structure parameter: 0.028 (16)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₂H₁₈N₂O₃S	V = 955.39 (4) Å³
M_r = 390.44	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 4.61595 (13) Å	µ = 1.72 mm⁻¹
b = 17.6844 (4) Å	T = 173 K
c = 11.7068 (3) Å	0.24 × 0.18 × 0.06 mm
β = 91.285 (3)°

Data collection top

Agilent Eos Gemini diffractometer	2781 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2610 reflections with I > 2σ(I)
T_min = 0.634, T_max = 1.000	R_int = 0.027
6206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.21 e Å⁻³
S = 1.02	Δρ_min = −0.19 e Å⁻³
2781 reflections	Absolute structure: Flack x determined using 764 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004)
263 parameters	Absolute structure parameter: 0.028 (16)
138 restraints

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)
S1	0.24441 (14)	0.70387 (3)	0.62913 (5)	0.03214 (17)
O1A	0.009 (2)	0.4397 (10)	0.5799 (16)	0.041 (2)	0.583 (5)
O1B	−0.071 (4)	0.4474 (15)	0.576 (2)	0.041 (2)	0.417 (5)
O2	−0.9787 (6)	0.75162 (18)	−0.0143 (2)	0.0605 (7)
O3	−1.1148 (6)	0.84877 (16)	0.0802 (2)	0.0551 (7)
N1	−0.0687 (5)	0.64901 (14)	0.44225 (18)	0.0293 (5)
N2	−0.9655 (6)	0.79235 (16)	0.0691 (2)	0.0385 (6)
C1	0.0964 (6)	0.49027 (16)	0.5199 (2)	0.0338 (6)
C2	0.1876 (6)	0.56264 (16)	0.5745 (2)	0.0280 (5)
C3	0.3469 (6)	0.56491 (16)	0.6813 (2)	0.0303 (6)
C4A	0.439 (6)	0.4943 (15)	0.7449 (16)	0.0392 (15)	0.583 (5)
H4AA	0.5141	0.4559	0.6915	0.047*	0.583 (5)
H4AB	0.2683	0.4731	0.7832	0.047*	0.583 (5)
C5A	0.6700 (13)	0.5148 (4)	0.8363 (5)	0.0438 (11)	0.583 (5)
H5AA	0.7031	0.4720	0.8895	0.053*	0.583 (5)
H5AB	0.8537	0.5248	0.7969	0.053*	0.583 (5)
C6A	0.5854 (15)	0.5850 (4)	0.9033 (5)	0.0428 (12)	0.583 (5)
H6AA	0.3961	0.5767	0.9394	0.051*	0.583 (5)
H6AB	0.7322	0.5949	0.9644	0.051*	0.583 (5)
C7A	0.578 (5)	0.6541 (8)	0.8218 (18)	0.035 (2)	0.583 (5)
H7AA	0.4883	0.6968	0.8628	0.042*	0.583 (5)
H7AB	0.7767	0.6695	0.8023	0.042*	0.583 (5)
C4B	0.464 (8)	0.502 (2)	0.754 (2)	0.0392 (15)	0.417 (5)
H4BA	0.6486	0.4861	0.7197	0.047*	0.417 (5)
H4BB	0.3324	0.4574	0.7522	0.047*	0.417 (5)
C5B	0.5365 (19)	0.5254 (5)	0.8763 (7)	0.0438 (11)	0.417 (5)
H5BA	0.3503	0.5333	0.9149	0.053*	0.417 (5)
H5BB	0.6429	0.4844	0.9169	0.053*	0.417 (5)
C6B	0.717 (2)	0.5966 (5)	0.8813 (8)	0.0428 (12)	0.417 (5)
H6BA	0.7592	0.6094	0.9623	0.051*	0.417 (5)
H6BB	0.9050	0.5874	0.8443	0.051*	0.417 (5)
C7B	0.551 (7)	0.6653 (12)	0.830 (3)	0.035 (2)	0.417 (5)
H7BA	0.6977	0.7031	0.8078	0.042*	0.417 (5)
H7BB	0.4169	0.6895	0.8834	0.042*	0.417 (5)
C8	0.3991 (6)	0.63650 (17)	0.7187 (2)	0.0310 (6)
C9	0.1092 (6)	0.63358 (15)	0.5361 (2)	0.0276 (6)
C10A	0.1914 (17)	0.4696 (6)	0.4023 (7)	0.0261 (15)	0.583 (5)
C11A	0.0684 (16)	0.4049 (6)	0.3543 (9)	0.0430 (17)	0.583 (5)
H11A	−0.0653	0.3758	0.3964	0.052*	0.583 (5)
C12A	0.1411 (17)	0.3828 (5)	0.2446 (9)	0.049 (2)	0.583 (5)
H12A	0.0571	0.3386	0.2118	0.059*	0.583 (5)
C13A	0.3367 (16)	0.4254 (6)	0.1830 (7)	0.050 (2)	0.583 (5)
H13A	0.3864	0.4103	0.1081	0.060*	0.583 (5)
C14A	0.4597 (16)	0.4901 (5)	0.2311 (9)	0.051 (2)	0.583 (5)
H14A	0.5934	0.5192	0.1889	0.061*	0.583 (5)
C15A	0.3870 (18)	0.5122 (5)	0.3407 (9)	0.0347 (17)	0.583 (5)
H15A	0.4711	0.5564	0.3735	0.042*	0.583 (5)
C10B	0.127 (3)	0.4756 (10)	0.3952 (11)	0.0261 (15)	0.417 (5)
C11B	−0.001 (3)	0.4119 (9)	0.3461 (13)	0.0430 (17)	0.417 (5)
H11B	−0.1300	0.3819	0.3890	0.052*	0.417 (5)
C12B	0.060 (3)	0.3922 (7)	0.2342 (14)	0.049 (2)	0.417 (5)
H12B	−0.0276	0.3487	0.2007	0.059*	0.417 (5)
C13B	0.249 (3)	0.4360 (9)	0.1715 (11)	0.050 (2)	0.417 (5)
H13B	0.2906	0.4225	0.0950	0.060*	0.417 (5)
C14B	0.377 (3)	0.4997 (8)	0.2206 (13)	0.051 (2)	0.417 (5)
H14B	0.5065	0.5297	0.1777	0.061*	0.417 (5)
C15B	0.316 (3)	0.5194 (8)	0.3324 (14)	0.0347 (17)	0.417 (5)
H15B	0.4041	0.5629	0.3660	0.042*	0.417 (5)
C16	−0.1906 (5)	0.71396 (17)	0.4340 (2)	0.0295 (6)
H16	−0.1542	0.7504	0.4921	0.035*
C17	−0.3839 (5)	0.73363 (15)	0.3379 (2)	0.0277 (5)
C18	−0.4040 (6)	0.68891 (15)	0.2402 (2)	0.0319 (6)
H18	−0.2870	0.6449	0.2344	0.038*
C19	−0.5926 (6)	0.70787 (19)	0.1514 (2)	0.0339 (6)
H19	−0.6052	0.6778	0.0841	0.041*
C20	−0.7634 (6)	0.77200 (16)	0.1630 (2)	0.0309 (6)
C21	−0.7499 (6)	0.81762 (16)	0.2582 (2)	0.0310 (6)
H21	−0.8692	0.8612	0.2637	0.037*
C22	−0.5568 (6)	0.79807 (16)	0.3461 (2)	0.0316 (6)
H22	−0.5423	0.8289	0.4124	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0408 (3)	0.0258 (3)	0.0297 (3)	0.0003 (3)	−0.0032 (2)	−0.0018 (3)
O1A	0.045 (6)	0.033 (4)	0.0448 (18)	−0.007 (5)	0.011 (5)	0.004 (2)
O1B	0.045 (6)	0.033 (4)	0.0448 (18)	−0.007 (5)	0.011 (5)	0.004 (2)
O2	0.0743 (17)	0.0657 (18)	0.0406 (12)	0.0136 (14)	−0.0202 (11)	−0.0143 (12)
O3	0.0636 (15)	0.0471 (14)	0.0538 (14)	0.0174 (12)	−0.0183 (12)	0.0023 (11)
N1	0.0326 (11)	0.0294 (12)	0.0260 (11)	−0.0036 (10)	0.0002 (8)	0.0008 (9)
N2	0.0416 (13)	0.0419 (15)	0.0318 (12)	−0.0038 (12)	−0.0050 (10)	0.0034 (11)
C1	0.0416 (16)	0.0271 (15)	0.0328 (14)	−0.0008 (13)	0.0061 (12)	0.0022 (12)
C2	0.0332 (13)	0.0263 (14)	0.0248 (12)	−0.0002 (10)	0.0061 (10)	0.0016 (10)
C3	0.0331 (13)	0.0318 (15)	0.0262 (12)	0.0040 (11)	0.0050 (10)	0.0013 (11)
C4A	0.047 (4)	0.035 (4)	0.036 (3)	0.009 (3)	0.002 (2)	0.004 (2)
C5A	0.044 (3)	0.052 (3)	0.034 (3)	0.013 (2)	−0.0027 (18)	0.005 (2)
C6A	0.040 (3)	0.054 (3)	0.034 (2)	0.005 (3)	−0.005 (2)	0.002 (2)
C7A	0.035 (4)	0.041 (4)	0.028 (3)	0.006 (3)	0.000 (2)	−0.007 (4)
C4B	0.047 (4)	0.035 (4)	0.036 (3)	0.009 (3)	0.002 (2)	0.004 (2)
C5B	0.044 (3)	0.052 (3)	0.034 (3)	0.013 (2)	−0.0027 (18)	0.005 (2)
C6B	0.040 (3)	0.054 (3)	0.034 (2)	0.005 (3)	−0.005 (2)	0.002 (2)
C7B	0.035 (4)	0.041 (4)	0.028 (3)	0.006 (3)	0.000 (2)	−0.007 (4)
C8	0.0310 (13)	0.0346 (16)	0.0274 (13)	0.0042 (11)	0.0025 (10)	0.0014 (11)
C9	0.0313 (13)	0.0247 (14)	0.0270 (13)	−0.0019 (10)	0.0035 (10)	−0.0015 (10)
C10A	0.021 (4)	0.025 (2)	0.0314 (16)	0.006 (3)	−0.008 (2)	0.0031 (15)
C11A	0.046 (4)	0.034 (3)	0.048 (2)	−0.008 (3)	0.000 (3)	−0.0066 (18)
C12A	0.057 (5)	0.040 (3)	0.050 (3)	−0.005 (3)	−0.010 (3)	−0.014 (2)
C13A	0.066 (5)	0.051 (4)	0.035 (2)	0.001 (4)	0.001 (3)	−0.016 (2)
C14A	0.065 (5)	0.047 (3)	0.041 (3)	−0.014 (4)	0.016 (3)	−0.011 (2)
C15A	0.036 (5)	0.033 (2)	0.036 (2)	−0.006 (3)	0.001 (3)	−0.0046 (18)
C10B	0.021 (4)	0.025 (2)	0.0314 (16)	0.006 (3)	−0.008 (2)	0.0031 (15)
C11B	0.046 (4)	0.034 (3)	0.048 (2)	−0.008 (3)	0.000 (3)	−0.0066 (18)
C12B	0.057 (5)	0.040 (3)	0.050 (3)	−0.005 (3)	−0.010 (3)	−0.014 (2)
C13B	0.066 (5)	0.051 (4)	0.035 (2)	0.001 (4)	0.001 (3)	−0.016 (2)
C14B	0.065 (5)	0.047 (3)	0.041 (3)	−0.014 (4)	0.016 (3)	−0.011 (2)
C15B	0.036 (5)	0.033 (2)	0.036 (2)	−0.006 (3)	0.001 (3)	−0.0046 (18)
C16	0.0319 (12)	0.0288 (15)	0.0279 (11)	−0.0029 (11)	0.0007 (9)	−0.0002 (11)
C17	0.0279 (12)	0.0257 (13)	0.0295 (12)	−0.0045 (10)	0.0009 (10)	0.0043 (10)
C18	0.0368 (13)	0.0284 (16)	0.0308 (13)	0.0034 (11)	0.0061 (10)	−0.0007 (10)
C19	0.0421 (14)	0.0324 (14)	0.0270 (11)	0.0005 (14)	0.0011 (10)	−0.0064 (13)
C20	0.0313 (13)	0.0319 (15)	0.0296 (12)	−0.0043 (11)	−0.0004 (10)	0.0039 (11)
C21	0.0332 (13)	0.0268 (13)	0.0330 (14)	−0.0008 (11)	0.0002 (10)	0.0016 (11)
C22	0.0375 (14)	0.0282 (14)	0.0292 (12)	−0.0039 (11)	−0.0001 (10)	−0.0031 (11)

Geometric parameters (Å, º) top

S1—C8	1.730 (3)	C7B—H7BA	0.9902
S1—C9	1.758 (3)	C7B—H7BB	0.9900
O1A—C1	1.213 (18)	C7B—C8	1.55 (4)
O1B—C1	1.27 (3)	C10A—C11A	1.3900
O2—N2	1.214 (4)	C10A—C15A	1.3900
O3—N2	1.221 (4)	C11A—H11A	0.9500
N1—C9	1.384 (3)	C11A—C12A	1.3900
N1—C16	1.282 (4)	C12A—H12A	0.9500
N2—C20	1.470 (3)	C12A—C13A	1.3900
C1—C2	1.487 (4)	C13A—H13A	0.9500
C1—C10A	1.499 (9)	C13A—C14A	1.3900
C1—C10B	1.493 (13)	C14A—H14A	0.9500
C2—C3	1.437 (4)	C14A—C15A	1.3900
C2—C9	1.378 (4)	C15A—H15A	0.9500
C3—C4A	1.51 (3)	C10B—C11B	1.3900
C3—C4B	1.50 (4)	C10B—C15B	1.3900
C3—C8	1.359 (4)	C11B—H11B	0.9500
C4A—H4AA	0.9898	C11B—C12B	1.3900
C4A—H4AB	0.9899	C12B—H12B	0.9500
C4A—C5A	1.537 (14)	C12B—C13B	1.3900
C5A—H5AA	0.9902	C13B—H13B	0.9500
C5A—H5AB	0.9899	C13B—C14B	1.3900
C5A—C6A	1.523 (9)	C14B—H14B	0.9500
C6A—H6AA	0.9900	C14B—C15B	1.3900
C6A—H6AB	0.9900	C15B—H15B	0.9500
C6A—C7A	1.550 (13)	C16—H16	0.9500
C7A—H7AA	0.9900	C16—C17	1.462 (3)
C7A—H7AB	0.9899	C17—C18	1.393 (4)
C7A—C8	1.48 (2)	C17—C22	1.396 (4)
C4B—H4BA	0.9900	C18—H18	0.9500
C4B—H4BB	0.9901	C18—C19	1.382 (4)
C4B—C5B	1.524 (17)	C19—H19	0.9500
C5B—H5BA	0.9900	C19—C20	1.389 (4)
C5B—H5BB	0.9899	C20—C21	1.377 (4)
C5B—C6B	1.511 (12)	C21—H21	0.9500
C6B—H6BA	0.9900	C21—C22	1.390 (4)
C6B—H6BB	0.9900	C22—H22	0.9500
C6B—C7B	1.553 (17)

C8—S1—C9	91.40 (14)	C8—C7B—H7BB	113.4
C16—N1—C9	119.2 (2)	C3—C8—S1	112.3 (2)
O2—N2—O3	123.5 (3)	C3—C8—C7A	123.4 (5)
O2—N2—C20	118.4 (3)	C3—C8—C7B	130.5 (6)
O3—N2—C20	118.1 (2)	C7A—C8—S1	124.3 (5)
O1A—C1—C2	118.8 (9)	C7B—C8—S1	117.1 (6)
O1A—C1—C10A	117.4 (10)	N1—C9—S1	123.3 (2)
O1B—C1—C2	117.5 (13)	C2—C9—S1	110.8 (2)
O1B—C1—C10B	118.0 (15)	C2—C9—N1	125.8 (2)
C2—C1—C10A	121.2 (5)	C11A—C10A—C1	116.5 (7)
C2—C1—C10B	122.5 (7)	C11A—C10A—C15A	120.0
C3—C2—C1	122.2 (2)	C15A—C10A—C1	123.5 (7)
C9—C2—C1	125.0 (2)	C10A—C11A—H11A	120.0
C9—C2—C3	112.6 (2)	C12A—C11A—C10A	120.0
C2—C3—C4A	122.6 (5)	C12A—C11A—H11A	120.0
C2—C3—C4B	130.1 (8)	C11A—C12A—H12A	120.0
C8—C3—C2	112.9 (2)	C11A—C12A—C13A	120.0
C8—C3—C4A	124.5 (5)	C13A—C12A—H12A	120.0
C8—C3—C4B	117.0 (8)	C12A—C13A—H13A	120.0
C3—C4A—H4AA	110.8	C14A—C13A—C12A	120.0
C3—C4A—H4AB	108.5	C14A—C13A—H13A	120.0
C3—C4A—C5A	109.3 (14)	C13A—C14A—H14A	120.0
H4AA—C4A—H4AB	108.6	C15A—C14A—C13A	120.0
C5A—C4A—H4AA	110.8	C15A—C14A—H14A	120.0
C5A—C4A—H4AB	108.7	C10A—C15A—H15A	120.0
C4A—C5A—H5AA	110.6	C14A—C15A—C10A	120.0
C4A—C5A—H5AB	107.8	C14A—C15A—H15A	120.0
H5AA—C5A—H5AB	107.9	C11B—C10B—C1	119.7 (11)
C6A—C5A—C4A	111.7 (11)	C11B—C10B—C15B	120.0
C6A—C5A—H5AA	109.7	C15B—C10B—C1	119.6 (10)
C6A—C5A—H5AB	109.0	C10B—C11B—H11B	120.0
C5A—C6A—H6AA	109.7	C12B—C11B—C10B	120.0
C5A—C6A—H6AB	109.7	C12B—C11B—H11B	120.0
C5A—C6A—C7A	109.1 (9)	C11B—C12B—H12B	120.0
H6AA—C6A—H6AB	108.3	C13B—C12B—C11B	120.0
C7A—C6A—H6AA	111.8	C13B—C12B—H12B	120.0
C7A—C6A—H6AB	108.2	C12B—C13B—H13B	120.0
C6A—C7A—H7AA	107.9	C14B—C13B—C12B	120.0
C6A—C7A—H7AB	110.4	C14B—C13B—H13B	120.0
H7AA—C7A—H7AB	107.5	C13B—C14B—H14B	120.0
C8—C7A—C6A	110.0 (13)	C13B—C14B—C15B	120.0
C8—C7A—H7AA	109.1	C15B—C14B—H14B	120.0
C8—C7A—H7AB	111.9	C10B—C15B—H15B	120.0
C3—C4B—H4BA	106.4	C14B—C15B—C10B	120.0
C3—C4B—H4BB	111.5	C14B—C15B—H15B	120.0
C3—C4B—C5B	113 (2)	N1—C16—H16	119.0
H4BA—C4B—H4BB	107.7	N1—C16—C17	122.0 (3)
C5B—C4B—H4BA	106.4	C17—C16—H16	119.0
C5B—C4B—H4BB	111.0	C18—C17—C16	121.7 (2)
C4B—C5B—H5BA	107.1	C18—C17—C22	119.5 (2)
C4B—C5B—H5BB	110.3	C22—C17—C16	118.8 (2)
H5BA—C5B—H5BB	108.2	C17—C18—H18	119.7
C6B—C5B—C4B	112.0 (16)	C19—C18—C17	120.6 (3)
C6B—C5B—H5BA	110.4	C19—C18—H18	119.7
C6B—C5B—H5BB	108.8	C18—C19—H19	120.9
C5B—C6B—H6BA	108.9	C18—C19—C20	118.3 (2)
C5B—C6B—H6BB	109.6	C20—C19—H19	120.9
C5B—C6B—C7B	111.6 (15)	C19—C20—N2	118.6 (2)
H6BA—C6B—H6BB	107.7	C21—C20—N2	118.6 (3)
C7B—C6B—H6BA	106.1	C21—C20—C19	122.8 (2)
C7B—C6B—H6BB	112.8	C20—C21—H21	121.0
C6B—C7B—H7BA	107.1	C20—C21—C22	118.1 (3)
C6B—C7B—H7BB	113.8	C22—C21—H21	121.0
H7BA—C7B—H7BB	108.2	C17—C22—H22	119.6
C8—C7B—C6B	106.3 (17)	C21—C22—C17	120.7 (3)
C8—C7B—H7BA	107.7	C21—C22—H22	119.6

O1A—C1—C2—C3	40.0 (6)	C4B—C3—C8—S1	−178.4 (18)
O1A—C1—C2—C9	−133.7 (5)	C4B—C3—C8—C7A	4 (2)
O1A—C1—C10A—C11A	25.5 (8)	C4B—C3—C8—C7B	−3 (2)
O1A—C1—C10A—C15A	−155.8 (7)	C4B—C5B—C6B—C7B	63 (2)
O1A—C1—C10B—C11B	14.0 (11)	C5B—C6B—C7B—C8	−43 (2)
O1A—C1—C10B—C15B	−157.1 (8)	C6B—C7B—C8—S1	−169.6 (11)
O1B—C1—C2—C3	60.5 (10)	C6B—C7B—C8—C3	16 (3)
O1B—C1—C2—C9	−113.2 (10)	C6B—C7B—C8—C7A	−25 (10)
O1B—C1—C10A—C11A	5.2 (11)	C8—S1—C9—N1	174.9 (2)
O1B—C1—C10A—C15A	−176.1 (10)	C8—S1—C9—C2	−0.8 (2)
O1B—C1—C10B—C11B	−6.6 (13)	C8—C3—C4A—C5A	−16 (2)
O1B—C1—C10B—C15B	−177.7 (11)	C8—C3—C4B—C5B	19 (3)
O2—N2—C20—C19	1.1 (4)	C9—S1—C8—C3	−1.1 (2)
O2—N2—C20—C21	−179.3 (3)	C9—S1—C8—C7A	176.7 (11)
O3—N2—C20—C19	179.9 (3)	C9—S1—C8—C7B	−176.8 (14)
O3—N2—C20—C21	−0.5 (4)	C9—N1—C16—C17	−179.2 (2)
N1—C16—C17—C18	−12.3 (4)	C9—C2—C3—C4A	175.7 (13)
N1—C16—C17—C22	166.3 (3)	C9—C2—C3—C4B	178 (2)
N2—C20—C21—C22	−179.6 (2)	C9—C2—C3—C8	−3.2 (3)
C1—C2—C3—C4A	1.3 (14)	C10A—C1—C2—C3	−121.2 (4)
C1—C2—C3—C4B	4 (2)	C10A—C1—C2—C9	65.1 (5)
C1—C2—C3—C8	−177.6 (3)	C10A—C1—C10B—C11B	102 (5)
C1—C2—C9—S1	176.5 (2)	C10A—C1—C10B—C15B	−69 (5)
C1—C2—C9—N1	1.0 (4)	C10A—C11A—C12A—C13A	0.0
C1—C10A—C11A—C12A	178.7 (6)	C11A—C10A—C15A—C14A	0.0
C1—C10A—C15A—C14A	−178.7 (7)	C11A—C12A—C13A—C14A	0.0
C1—C10B—C11B—C12B	−171.1 (11)	C12A—C13A—C14A—C15A	0.0
C1—C10B—C15B—C14B	171.1 (11)	C13A—C14A—C15A—C10A	0.0
C2—C1—C10A—C11A	−173.1 (3)	C15A—C10A—C11A—C12A	0.0
C2—C1—C10A—C15A	5.6 (7)	C10B—C1—C2—C3	−135.7 (7)
C2—C1—C10B—C11B	−170.3 (5)	C10B—C1—C2—C9	50.6 (7)
C2—C1—C10B—C15B	18.6 (11)	C10B—C1—C10A—C11A	−73 (5)
C2—C3—C4A—C5A	164.9 (8)	C10B—C1—C10A—C15A	105 (5)
C2—C3—C4B—C5B	−162.1 (11)	C10B—C11B—C12B—C13B	0.0
C2—C3—C8—S1	2.6 (3)	C11B—C10B—C15B—C14B	0.0
C2—C3—C8—C7A	−175.2 (11)	C11B—C12B—C13B—C14B	0.0
C2—C3—C8—C7B	177.6 (17)	C12B—C13B—C14B—C15B	0.0
C3—C2—C9—S1	2.3 (3)	C13B—C14B—C15B—C10B	0.0
C3—C2—C9—N1	−173.3 (2)	C15B—C10B—C11B—C12B	0.0
C3—C4A—C5A—C6A	45.5 (19)	C16—N1—C9—S1	−14.8 (4)
C3—C4B—C5B—C6B	−49 (3)	C16—N1—C9—C2	160.3 (3)
C4A—C3—C4B—C5B	−148 (21)	C16—C17—C18—C19	178.7 (2)
C4A—C3—C8—S1	−176.3 (13)	C16—C17—C22—C21	−178.1 (2)
C4A—C3—C8—C7A	5.9 (17)	C17—C18—C19—C20	−0.8 (4)
C4A—C3—C8—C7B	−1 (2)	C18—C17—C22—C21	0.5 (4)
C4A—C5A—C6A—C7A	−65.1 (16)	C18—C19—C20—N2	−179.7 (2)
C5A—C6A—C7A—C8	51.0 (15)	C18—C19—C20—C21	0.8 (4)
C6A—C7A—C8—S1	159.4 (6)	C19—C20—C21—C22	−0.1 (4)
C6A—C7A—C8—C3	−23.0 (18)	C20—C21—C22—C17	−0.6 (4)
C6A—C7A—C8—C7B	120 (13)	C22—C17—C18—C19	0.2 (4)
C4B—C3—C4A—C5A	−2 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AA···O1Bⁱ	0.99	2.38	3.15 (4)	135
C4B—H4BA···O1Aⁱ	0.99	2.50	3.45 (4)	162
C4B—H4BA···O1Bⁱ	0.99	2.26	3.18 (4)	154
C7B—H7BB···O2ⁱⁱ	0.99	2.46	3.44 (3)	169
C13B—H13B···O3ⁱⁱⁱ	0.95	2.55	3.371 (13)	145
C21—H21···O1A^iv	0.95	2.40	3.127 (18)	133
C21—H21···O1B^iv	0.95	2.44	3.13 (3)	129

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AA···O1Bⁱ	0.99	2.38	3.15 (4)	135
C4B—H4BA···O1Aⁱ	0.99	2.50	3.45 (4)	162
C4B—H4BA···O1Bⁱ	0.99	2.26	3.18 (4)	154
C7B—H7BB···O2ⁱⁱ	0.99	2.46	3.44 (3)	169
C13B—H13B···O3ⁱⁱⁱ	0.95	2.55	3.371 (13)	145
C21—H21···O1A^iv	0.95	2.40	3.127 (18)	133
C21—H21···O1B^iv	0.95	2.44	3.13 (3)	129

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

Acknowledgements

MK is grateful to CPEPA–UGC for the award of a JRF 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 6| June 2014| Pages o738-o739

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

{2-[(4-Nitro­benzyl­­idene)amino]-4,5,6,7-tetra­hydro-1-benzo­thio­phen-3-yl}(phen­yl)methanone

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Experimental

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organic compounds

{2-[(4-Nitrobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}(phenyl)methanone