[2-(Benzyl-idene-amino)-4,5,6,7-tetra-hydro-benzo[b]thio-phen-3-yl](phen-yl)methanone.

In the title compound, C22H19NOS, the cyclo-hexene ring of the tetra-hydro-benzo-thio-phenyl ring system adopts a slightly distorted half-chair conformation and is twisted slightly [7.5 (8)° for the major disorder component] from the mean plane of the thio-phene ring. The dihedral angles between the mean planes of the thio-phene ring and the phenyl rings are 65.7 (3) and 8.3 (4)°. The phenyl rings are twisted with respect to each other by 73.8 (7)°. Disorder was modeled for four C atoms of the cyclo-hexene ring over two sets of sites with an occupancy ratio of 0.659 (2):0.341 (2). In the crystal, a single weak C-H⋯O inter-action links the mol-ecules into [001] chains.

Related literature

For the importance of thio­phene derivatives, see: Molvi et al. (2007 ▶); Rai et al. (2008 ▶); Asthalatha et al. (2007 ▶). For applications of 2-amino­thio­phene derivatives, see: Sabnis et al. (1999 ▶); Puterová et al. (2010 ▶); Cannito et al. (1990 ▶); Nikolakopoulos et al. (2006 ▶); Lütjens et al. (2005 ▶). 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

C22H19NOS

M = 345.44

Monoclinic,

a = 8.78760 (16) Å

b = 14.0091 (3) Å

c = 14.4120 (2) Å

β = 94.8913 (17)°

V = 1767.75 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.24 × 0.22 × 0.12 mm

Data collection

Agilent Eos, Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.896, T max = 1.000

22680 measured reflections

6047 independent reflections

4745 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.03

6047 reflections

239 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814006679/zs2292sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006679/zs2292Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006679/zs2292Isup3.cml

CCDC reference: 993683

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H19NOS	F(000) = 728
Mr = 345.44	Dx = 1.298 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.78760 (16) Å	Cell parameters from 6837 reflections
b = 14.0091 (3) Å	θ = 3.9–32.5°
c = 14.4120 (2) Å	µ = 0.19 mm−1
β = 94.8913 (17)°	T = 173 K
V = 1767.75 (5) Å3	Irregular, yellow
Z = 4	0.24 × 0.22 × 0.12 mm

Agilent Eos, Gemini diffractometer	6047 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4745 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.029
ω scans	θmax = 32.9°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −13→13
Tmin = 0.896, Tmax = 1.000	k = −20→18
22680 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.5445P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6047 reflections	Δρmax = 0.39 e Å−3
239 parameters	Δρmin = −0.25 e Å−3
48 restraints

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.43796 (4)	0.38720 (2)	0.29828 (2)	0.02980 (8)
O1	0.24466 (11)	0.32510 (7)	0.59768 (6)	0.0331 (2)
N1	0.38490 (11)	0.20786 (7)	0.37310 (7)	0.02681 (19)
C1	0.36366 (13)	0.30555 (8)	0.37431 (8)	0.0252 (2)
C2	0.28925 (12)	0.35256 (8)	0.44102 (7)	0.0242 (2)
C3	0.29554 (12)	0.45436 (8)	0.43292 (8)	0.0256 (2)
C4	0.2295 (15)	0.5272 (10)	0.4954 (9)	0.0321 (5)	0.659 (2)
H4A	0.2554	0.5088	0.5612	0.038*	0.659 (2)
H4B	0.1169	0.5270	0.4838	0.038*	0.659 (2)
C4A	0.232 (3)	0.523 (2)	0.4994 (18)	0.0321 (5)	0.341 (2)
H4AA	0.3050	0.5316	0.5550	0.038*	0.341 (2)
H4AB	0.1347	0.4984	0.5198	0.038*	0.341 (2)
C5	0.2890 (2)	0.62862 (13)	0.47989 (14)	0.0319 (3)	0.659 (2)
H5A	0.2274	0.6752	0.5123	0.038*	0.659 (2)
H5B	0.3963	0.6337	0.5066	0.038*	0.659 (2)
C5A	0.2063 (4)	0.6169 (3)	0.4479 (3)	0.0319 (3)	0.341 (2)
H5AA	0.1771	0.6663	0.4921	0.038*	0.341 (2)
H5AB	0.1208	0.6095	0.3991	0.038*	0.341 (2)
C6	0.2800 (3)	0.65215 (15)	0.37652 (16)	0.0358 (4)	0.659 (2)
H6A	0.1733	0.6457	0.3492	0.043*	0.659 (2)
H6B	0.3129	0.7189	0.3678	0.043*	0.659 (2)
C6A	0.3481 (6)	0.6498 (3)	0.4029 (3)	0.0358 (4)	0.341 (2)
H6AA	0.4342	0.6544	0.4516	0.043*	0.341 (2)
H6AB	0.3291	0.7145	0.3768	0.043*	0.341 (2)
C7	0.3826 (19)	0.5846 (14)	0.3276 (11)	0.0324 (10)	0.659 (2)
H7A	0.3563	0.5888	0.2595	0.039*	0.659 (2)
H7B	0.4901	0.6053	0.3404	0.039*	0.659 (2)
C7A	0.396 (4)	0.583 (3)	0.324 (2)	0.0324 (10)	0.341 (2)
H7AA	0.3326	0.5955	0.2649	0.039*	0.341 (2)
H7AB	0.5045	0.5921	0.3135	0.039*	0.341 (2)
C8	0.36852 (13)	0.48275 (8)	0.35769 (8)	0.0270 (2)
C9	0.21326 (13)	0.30278 (8)	0.51617 (8)	0.0249 (2)
C10	0.09322 (12)	0.23048 (8)	0.49013 (7)	0.0247 (2)
C11	0.04152 (14)	0.17248 (10)	0.55985 (8)	0.0323 (3)
H11	0.0872	0.1772	0.6218	0.039*
C12	−0.07579 (16)	0.10824 (11)	0.53899 (10)	0.0393 (3)
H12	−0.1096	0.0685	0.5865	0.047*
C13	−0.14437 (15)	0.10158 (11)	0.44890 (10)	0.0389 (3)
H13	−0.2253	0.0576	0.4348	0.047*
C14	−0.09461 (14)	0.15925 (11)	0.37946 (9)	0.0354 (3)
H14	−0.1421	0.1551	0.3179	0.042*
C15	0.02434 (13)	0.22300 (9)	0.39966 (8)	0.0297 (2)
H15	0.0590	0.2617	0.3516	0.036*
C16	0.46997 (13)	0.16863 (8)	0.31614 (8)	0.0266 (2)
H16	0.5178	0.2077	0.2732	0.032*
C17	0.49574 (13)	0.06571 (8)	0.31511 (8)	0.0249 (2)
C18	0.58705 (14)	0.02651 (9)	0.25008 (8)	0.0295 (2)
H18	0.6283	0.0665	0.2052	0.035*
C19	0.61767 (16)	−0.07066 (10)	0.25078 (9)	0.0352 (3)
H19	0.6790	−0.0971	0.2061	0.042*
C20	0.55903 (16)	−0.12931 (9)	0.31650 (10)	0.0366 (3)
H20	0.5809	−0.1957	0.3172	0.044*
C21	0.46824 (17)	−0.09070 (10)	0.38127 (9)	0.0378 (3)
H21	0.4284	−0.1309	0.4265	0.045*
C22	0.43529 (15)	0.00601 (9)	0.38046 (8)	0.0318 (2)
H22	0.3716	0.0317	0.4243	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.03553 (16)	0.02847 (15)	0.02699 (14)	−0.00477 (11)	0.01203 (11)	−0.00210 (10)
O1	0.0397 (5)	0.0347 (5)	0.0252 (4)	−0.0062 (4)	0.0050 (3)	−0.0039 (3)
N1	0.0272 (4)	0.0253 (5)	0.0284 (4)	−0.0026 (4)	0.0051 (4)	−0.0034 (4)
C1	0.0254 (5)	0.0259 (5)	0.0248 (5)	−0.0038 (4)	0.0050 (4)	−0.0017 (4)
C2	0.0227 (5)	0.0255 (5)	0.0247 (5)	−0.0027 (4)	0.0048 (4)	−0.0016 (4)
C3	0.0234 (5)	0.0261 (5)	0.0276 (5)	−0.0023 (4)	0.0042 (4)	−0.0024 (4)
C4	0.0324 (7)	0.0280 (13)	0.0370 (12)	0.0004 (7)	0.0102 (7)	−0.0051 (9)
C4A	0.0324 (7)	0.0280 (13)	0.0370 (12)	0.0004 (7)	0.0102 (7)	−0.0051 (9)
C5	0.0309 (8)	0.0251 (7)	0.0393 (9)	0.0007 (7)	−0.0001 (6)	−0.0055 (6)
C5A	0.0309 (8)	0.0251 (7)	0.0393 (9)	0.0007 (7)	−0.0001 (6)	−0.0055 (6)
C6	0.0434 (13)	0.0235 (7)	0.0396 (11)	0.0008 (9)	−0.0026 (8)	−0.0002 (7)
C6A	0.0434 (13)	0.0235 (7)	0.0396 (11)	0.0008 (9)	−0.0026 (8)	−0.0002 (7)
C7	0.035 (3)	0.0269 (9)	0.0360 (14)	−0.0065 (16)	0.0068 (14)	0.0024 (8)
C7A	0.035 (3)	0.0269 (9)	0.0360 (14)	−0.0065 (16)	0.0068 (14)	0.0024 (8)
C8	0.0272 (5)	0.0261 (5)	0.0282 (5)	−0.0038 (4)	0.0047 (4)	−0.0013 (4)
C9	0.0247 (5)	0.0250 (5)	0.0258 (5)	−0.0002 (4)	0.0061 (4)	−0.0006 (4)
C10	0.0230 (5)	0.0275 (5)	0.0243 (5)	−0.0011 (4)	0.0057 (4)	−0.0007 (4)
C11	0.0327 (6)	0.0387 (7)	0.0260 (5)	−0.0081 (5)	0.0050 (4)	0.0032 (5)
C12	0.0385 (7)	0.0443 (8)	0.0359 (6)	−0.0144 (6)	0.0082 (5)	0.0059 (5)
C13	0.0325 (6)	0.0449 (8)	0.0396 (7)	−0.0137 (6)	0.0048 (5)	−0.0028 (6)
C14	0.0290 (6)	0.0480 (8)	0.0290 (6)	−0.0081 (5)	0.0018 (5)	−0.0038 (5)
C15	0.0270 (5)	0.0373 (6)	0.0252 (5)	−0.0033 (5)	0.0057 (4)	0.0012 (4)
C16	0.0276 (5)	0.0260 (5)	0.0266 (5)	−0.0026 (4)	0.0050 (4)	−0.0006 (4)
C17	0.0243 (5)	0.0256 (5)	0.0250 (5)	−0.0016 (4)	0.0027 (4)	−0.0024 (4)
C18	0.0316 (6)	0.0300 (6)	0.0277 (5)	−0.0004 (4)	0.0070 (4)	−0.0009 (4)
C19	0.0379 (6)	0.0329 (6)	0.0355 (6)	0.0056 (5)	0.0082 (5)	−0.0041 (5)
C20	0.0447 (7)	0.0261 (6)	0.0387 (7)	0.0029 (5)	0.0015 (6)	−0.0015 (5)
C21	0.0505 (8)	0.0284 (6)	0.0356 (6)	−0.0072 (5)	0.0101 (6)	0.0013 (5)
C22	0.0370 (6)	0.0292 (6)	0.0305 (5)	−0.0057 (5)	0.0108 (5)	−0.0036 (4)

S1—C1	1.7485 (11)	C7—H7B	0.9900
S1—C8	1.7282 (12)	C7—C8	1.50 (2)
O1—C9	1.2241 (14)	C7A—H7AA	0.9900
N1—C1	1.3815 (15)	C7A—H7AB	0.9900
N1—C16	1.2804 (15)	C7A—C8	1.51 (4)
C1—C2	1.3758 (15)	C9—C10	1.4873 (16)
C2—C3	1.4323 (16)	C10—C11	1.3978 (16)
C2—C9	1.4930 (15)	C10—C15	1.3938 (15)
C3—C4	1.509 (16)	C11—H11	0.9500
C3—C4A	1.50 (3)	C11—C12	1.3821 (18)
C3—C8	1.3651 (16)	C12—H12	0.9500
C4—H4A	0.9900	C12—C13	1.3872 (19)
C4—H4B	0.9900	C13—H13	0.9500
C4—C5	1.537 (13)	C13—C14	1.3856 (19)
C4A—H4AA	0.9900	C14—H14	0.9500
C4A—H4AB	0.9900	C14—C15	1.3868 (17)
C4A—C5A	1.52 (3)	C15—H15	0.9500
C5—H5A	0.9900	C16—H16	0.9500
C5—H5B	0.9900	C16—C17	1.4597 (16)
C5—C6	1.521 (3)	C17—C18	1.3973 (15)
C5A—H5AA	0.9900	C17—C22	1.3978 (16)
C5A—H5AB	0.9900	C18—H18	0.9500
C5A—C6A	1.524 (6)	C18—C19	1.3874 (18)
C6—H6A	0.9900	C19—H19	0.9500
C6—H6B	0.9900	C19—C20	1.3860 (19)
C6—C7	1.521 (15)	C20—H20	0.9500
C6A—H6AA	0.9900	C20—C21	1.3883 (19)
C6A—H6AB	0.9900	C21—H21	0.9500
C6A—C7A	1.56 (3)	C21—C22	1.3852 (18)
C7—H7A	0.9900	C22—H22	0.9500
C8—S1—C1	91.70 (5)	C8—C7—H7B	109.0
C16—N1—C1	121.35 (10)	C6A—C7A—H7AA	110.7
N1—C1—S1	125.59 (8)	C6A—C7A—H7AB	110.7
C2—C1—S1	110.48 (8)	H7AA—C7A—H7AB	108.8
C2—C1—N1	123.77 (10)	C8—C7A—C6A	105 (2)
C1—C2—C3	113.31 (10)	C8—C7A—H7AA	110.7
C1—C2—C9	123.50 (10)	C8—C7A—H7AB	110.7
C3—C2—C9	123.16 (10)	C3—C8—S1	112.18 (9)
C2—C3—C4	127.2 (5)	C3—C8—C7	124.3 (6)
C2—C3—C4A	124.6 (9)	C3—C8—C7A	128.7 (11)
C8—C3—C2	112.26 (10)	C7—C8—S1	123.5 (6)
C8—C3—C4	120.5 (5)	C7A—C8—S1	119.2 (11)
C8—C3—C4A	123.2 (9)	O1—C9—C2	119.91 (10)
C3—C4—H4A	109.1	O1—C9—C10	120.87 (10)
C3—C4—H4B	109.1	C10—C9—C2	119.12 (9)
C3—C4—C5	112.7 (8)	C11—C10—C9	118.78 (10)
H4A—C4—H4B	107.8	C15—C10—C9	121.96 (10)
C5—C4—H4A	109.1	C15—C10—C11	119.14 (11)
C5—C4—H4B	109.1	C10—C11—H11	119.9
C3—C4A—H4AA	110.3	C12—C11—C10	120.29 (12)
C3—C4A—H4AB	110.3	C12—C11—H11	119.9
C3—C4A—C5A	106.9 (16)	C11—C12—H12	119.9
H4AA—C4A—H4AB	108.6	C11—C12—C13	120.25 (12)
C5A—C4A—H4AA	110.3	C13—C12—H12	119.9
C5A—C4A—H4AB	110.3	C12—C13—H13	120.1
C4—C5—H5A	109.5	C14—C13—C12	119.88 (12)
C4—C5—H5B	109.5	C14—C13—H13	120.1
H5A—C5—H5B	108.1	C13—C14—H14	119.9
C6—C5—C4	110.7 (5)	C13—C14—C15	120.16 (12)
C6—C5—H5A	109.5	C15—C14—H14	119.9
C6—C5—H5B	109.5	C10—C15—H15	119.9
C4A—C5A—H5AA	109.2	C14—C15—C10	120.28 (11)
C4A—C5A—H5AB	109.2	C14—C15—H15	119.9
C4A—C5A—C6A	112.1 (11)	N1—C16—H16	119.0
H5AA—C5A—H5AB	107.9	N1—C16—C17	122.01 (10)
C6A—C5A—H5AA	109.2	C17—C16—H16	119.0
C6A—C5A—H5AB	109.2	C18—C17—C16	119.57 (10)
C5—C6—H6A	109.7	C18—C17—C22	119.32 (11)
C5—C6—H6B	109.7	C22—C17—C16	121.06 (10)
H6A—C6—H6B	108.2	C17—C18—H18	119.9
C7—C6—C5	109.6 (7)	C19—C18—C17	120.19 (11)
C7—C6—H6A	109.7	C19—C18—H18	119.9
C7—C6—H6B	109.7	C18—C19—H19	119.9
C5A—C6A—H6AA	108.7	C20—C19—C18	120.23 (12)
C5A—C6A—H6AB	108.7	C20—C19—H19	119.9
C5A—C6A—C7A	114.0 (14)	C19—C20—H20	120.1
H6AA—C6A—H6AB	107.6	C19—C20—C21	119.79 (12)
C7A—C6A—H6AA	108.7	C21—C20—H20	120.1
C7A—C6A—H6AB	108.7	C20—C21—H21	119.8
C6—C7—H7A	109.0	C22—C21—C20	120.47 (12)
C6—C7—H7B	109.0	C22—C21—H21	119.8
H7A—C7—H7B	107.8	C17—C22—H22	120.0
C8—C7—C6	113.0 (11)	C21—C22—C17	119.98 (11)
C8—C7—H7A	109.0	C21—C22—H22	120.0
S1—C1—C2—C3	−1.73 (12)	C4A—C3—C8—C7A	−2 (2)
S1—C1—C2—C9	179.95 (9)	C4A—C5A—C6A—C7A	65.0 (19)
O1—C9—C10—C11	−14.66 (17)	C5—C6—C7—C8	44.1 (12)
O1—C9—C10—C15	161.26 (12)	C5A—C6A—C7A—C8	−39 (2)
N1—C1—C2—C3	173.90 (10)	C6—C7—C8—S1	165.8 (6)
N1—C1—C2—C9	−4.42 (18)	C6—C7—C8—C3	−11.9 (15)
N1—C16—C17—C18	178.62 (11)	C6—C7—C8—C7A	−164 (23)
N1—C16—C17—C22	−3.83 (18)	C6A—C7A—C8—S1	−169.1 (10)
C1—S1—C8—C3	1.38 (9)	C6A—C7A—C8—C3	10 (3)
C1—S1—C8—C7	−176.6 (8)	C6A—C7A—C8—C7	40 (21)
C1—S1—C8—C7A	−179.6 (15)	C8—S1—C1—N1	−175.30 (10)
C1—N1—C16—C17	178.88 (10)	C8—S1—C1—C2	0.23 (9)
C1—C2—C3—C4	−178.5 (6)	C8—C3—C4—C5	−14.7 (10)
C1—C2—C3—C4A	−176.3 (12)	C8—C3—C4A—C5A	22.6 (19)
C1—C2—C3—C8	2.81 (14)	C9—C2—C3—C4	−0.2 (6)
C1—C2—C9—O1	127.09 (13)	C9—C2—C3—C4A	2.0 (12)
C1—C2—C9—C10	−56.53 (15)	C9—C2—C3—C8	−178.86 (10)
C2—C3—C4—C5	166.7 (4)	C9—C10—C11—C12	176.41 (12)
C2—C3—C4A—C5A	−158.4 (7)	C9—C10—C15—C14	−175.46 (12)
C2—C3—C8—S1	−2.58 (13)	C10—C11—C12—C13	−0.7 (2)
C2—C3—C8—C7	175.4 (8)	C11—C10—C15—C14	0.45 (18)
C2—C3—C8—C7A	178.5 (17)	C11—C12—C13—C14	0.3 (2)
C2—C9—C10—C11	169.00 (11)	C12—C13—C14—C15	0.5 (2)
C2—C9—C10—C15	−15.07 (16)	C13—C14—C15—C10	−0.9 (2)
C3—C2—C9—O1	−51.06 (16)	C15—C10—C11—C12	0.37 (19)
C3—C2—C9—C10	125.31 (12)	C16—N1—C1—S1	3.22 (17)
C3—C4—C5—C6	47.5 (9)	C16—N1—C1—C2	−171.74 (11)
C3—C4A—C5A—C6A	−51.6 (16)	C16—C17—C18—C19	177.34 (12)
C4—C3—C4A—C5A	−11 (25)	C16—C17—C22—C21	−176.47 (12)
C4—C3—C8—S1	178.7 (6)	C17—C18—C19—C20	−0.6 (2)
C4—C3—C8—C7	−3.4 (10)	C18—C17—C22—C21	1.09 (18)
C4—C3—C8—C7A	−0.3 (18)	C18—C19—C20—C21	0.6 (2)
C4—C5—C6—C7	−62.7 (10)	C19—C20—C21—C22	0.3 (2)
C4A—C3—C4—C5	132 (26)	C20—C21—C22—C17	−1.1 (2)
C4A—C3—C8—S1	176.6 (11)	C22—C17—C18—C19	−0.25 (18)
C4A—C3—C8—C7	−5.5 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1i	0.95	2.45	3.4034 (15)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1i	0.95	2.45	3.4034 (15)	176

Symmetry code: (i) .