{2-[(2-Hy-droxy-benzyl-idene)amino]-4,5,6,7-tetra-hydro-1-benzo-thio-phen-3-yl}(phen-yl)methanone.

In the title compound, C22H19NO2S, the cyclo-hexene ring adopts a slightly distorted half-chair conformation. The dihedral angles between the mean planes of the thio-phene ring and the phenyl and 2-hy-droxy-phenyl rings are 70.4 (5) and 12.1 (9)°, respectively. The phenyl and 2-hy-droxy-phenyl rings are twisted with respect to one another by 81.0 (6)°. A short intra-molecular O-H⋯N hydrogen bond is observed. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into zigzag chains diagonally along [100] .

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

C22H19NO2S

M = 361.44

Monoclinic,

a = 9.26395 (15) Å

b = 14.2886 (2) Å

c = 13.6476 (2) Å

β = 96.7581 (15)°

V = 1793.97 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.73 mm−1

T = 173 K

0.24 × 0.14 × 0.08 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.658, T max = 1.000

11611 measured reflections

3462 independent reflections

3113 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.06

3462 reflections

237 parameters

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.26 e Å−3

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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814006199/sj5393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006199/sj5393Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006199/sj5393Isup3.cml

CCDC reference: 992723

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

C22H19NO2S	F(000) = 760
Mr = 361.44	Dx = 1.338 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 9.26395 (15) Å	Cell parameters from 5377 reflections
b = 14.2886 (2) Å	θ = 4.5–71.3°
c = 13.6476 (2) Å	µ = 1.73 mm−1
β = 96.7581 (15)°	T = 173 K
V = 1793.97 (5) Å3	Block, yellow
Z = 4	0.24 × 0.14 × 0.08 mm

Agilent Eos Gemini diffractometer	3462 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3113 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.053
ω scans	θmax = 71.5°, θmin = 4.5°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −11→10
Tmin = 0.658, Tmax = 1.000	k = −17→17
11611 measured reflections	l = −16→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0863P)2 + 0.6814P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 1.03 e Å−3
3462 reflections	Δρmin = −0.26 e Å−3
237 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0024 (4)
Primary atom site location: structure-invariant direct methods

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
S1	0.55854 (5)	0.11521 (3)	0.69557 (3)	0.02933 (18)
O1	0.74691 (15)	0.17574 (10)	0.38642 (9)	0.0336 (3)
O2	0.69355 (16)	0.45879 (10)	0.56596 (11)	0.0364 (4)
H2	0.6928	0.4014	0.5663	0.055*
N1	0.61684 (16)	0.29064 (11)	0.62125 (11)	0.0259 (3)
C1	0.77920 (18)	0.19624 (12)	0.47290 (13)	0.0243 (4)
C2	0.70603 (18)	0.14805 (12)	0.55066 (13)	0.0248 (4)
C3	0.70100 (18)	0.04840 (12)	0.56039 (13)	0.0255 (4)
C4	0.7719 (2)	−0.02126 (13)	0.49863 (15)	0.0312 (4)
H4A	0.8641	0.0034	0.4832	0.037*
H4B	0.7103	−0.0316	0.4370	0.037*
C5	0.7967 (3)	−0.11336 (16)	0.5535 (2)	0.0470 (6)
H5A	0.8254	−0.1606	0.5086	0.056*
H5B	0.8757	−0.1059	0.6063	0.056*
C6	0.6632 (3)	−0.14608 (16)	0.5964 (2)	0.0502 (6)
H6A	0.6840	−0.2058	0.6288	0.060*
H6B	0.5858	−0.1560	0.5430	0.060*
C7	0.6102 (2)	−0.07799 (14)	0.67023 (15)	0.0340 (4)
H7A	0.5088	−0.0902	0.6767	0.041*
H7B	0.6658	−0.0868	0.7344	0.041*
C8	0.62751 (19)	0.02115 (12)	0.63622 (14)	0.0271 (4)
C9	0.63331 (18)	0.19440 (12)	0.61848 (13)	0.0249 (4)
C10	0.89550 (18)	0.26513 (12)	0.50409 (13)	0.0243 (4)
C11	0.9396 (2)	0.32721 (14)	0.43438 (13)	0.0304 (4)
H11	0.8930	0.3271	0.3702	0.036*
C12	1.0525 (2)	0.38872 (15)	0.46073 (15)	0.0364 (5)
H12	1.0806	0.4307	0.4145	0.044*
C13	1.1242 (2)	0.38818 (15)	0.55585 (16)	0.0369 (5)
H13	1.2010	0.4292	0.5730	0.044*
C14	1.0813 (2)	0.32637 (16)	0.62539 (14)	0.0345 (4)
H14	1.1297	0.3257	0.6891	0.041*
C15	0.96629 (19)	0.26566 (14)	0.59984 (13)	0.0291 (4)
H15	0.9364	0.2252	0.6468	0.035*
C16	0.52973 (19)	0.33090 (13)	0.67519 (14)	0.0272 (4)
H16	0.4764	0.2942	0.7143	0.033*
C17	0.51257 (19)	0.43151 (13)	0.67668 (13)	0.0261 (4)
C18	0.4120 (2)	0.47131 (14)	0.73438 (14)	0.0309 (4)
H18	0.3603	0.4329	0.7728	0.037*
C19	0.3894 (2)	0.56679 (15)	0.73455 (15)	0.0359 (5)
H19	0.3225	0.5924	0.7727	0.043*
C20	0.4668 (2)	0.62451 (14)	0.67759 (16)	0.0361 (5)
H20	0.4501	0.6887	0.6769	0.043*
C21	0.5681 (2)	0.58765 (14)	0.62214 (16)	0.0355 (4)
H21	0.6205	0.6271	0.5852	0.043*
C22	0.5925 (2)	0.49131 (13)	0.62120 (14)	0.0281 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0347 (3)	0.0245 (3)	0.0310 (3)	−0.00448 (16)	0.01296 (19)	−0.00091 (16)
O1	0.0390 (7)	0.0356 (8)	0.0264 (7)	−0.0060 (6)	0.0048 (5)	−0.0032 (5)
O2	0.0406 (8)	0.0252 (7)	0.0470 (8)	−0.0044 (6)	0.0205 (6)	−0.0017 (6)
N1	0.0265 (7)	0.0222 (7)	0.0295 (8)	−0.0025 (6)	0.0055 (6)	−0.0010 (6)
C1	0.0241 (8)	0.0230 (8)	0.0260 (8)	0.0024 (6)	0.0046 (6)	0.0006 (7)
C2	0.0220 (8)	0.0239 (9)	0.0284 (9)	−0.0022 (7)	0.0027 (6)	−0.0012 (7)
C3	0.0225 (8)	0.0228 (8)	0.0309 (9)	−0.0020 (6)	0.0017 (7)	−0.0018 (7)
C4	0.0310 (9)	0.0273 (9)	0.0359 (10)	0.0022 (7)	0.0063 (7)	−0.0044 (8)
C5	0.0515 (13)	0.0336 (12)	0.0557 (14)	0.0093 (9)	0.0060 (11)	−0.0040 (9)
C6	0.0622 (15)	0.0241 (10)	0.0659 (16)	−0.0026 (10)	0.0144 (12)	−0.0007 (10)
C7	0.0365 (10)	0.0248 (9)	0.0407 (11)	−0.0068 (8)	0.0042 (8)	0.0043 (8)
C8	0.0277 (9)	0.0215 (9)	0.0322 (9)	−0.0019 (7)	0.0034 (7)	−0.0023 (7)
C9	0.0251 (8)	0.0234 (9)	0.0266 (8)	−0.0039 (7)	0.0047 (6)	0.0002 (7)
C10	0.0230 (8)	0.0255 (9)	0.0255 (8)	0.0007 (7)	0.0067 (6)	−0.0001 (7)
C11	0.0321 (9)	0.0353 (10)	0.0238 (8)	−0.0046 (8)	0.0041 (7)	0.0038 (7)
C12	0.0396 (11)	0.0389 (11)	0.0319 (10)	−0.0114 (8)	0.0097 (8)	0.0040 (8)
C13	0.0311 (10)	0.0429 (12)	0.0372 (11)	−0.0131 (8)	0.0064 (8)	−0.0058 (8)
C14	0.0297 (9)	0.0467 (12)	0.0266 (9)	−0.0043 (8)	0.0016 (7)	−0.0025 (8)
C15	0.0281 (9)	0.0347 (10)	0.0253 (9)	−0.0013 (7)	0.0060 (7)	0.0028 (7)
C16	0.0271 (8)	0.0250 (9)	0.0303 (9)	−0.0034 (7)	0.0063 (7)	−0.0006 (7)
C17	0.0246 (8)	0.0245 (9)	0.0288 (9)	−0.0011 (7)	0.0008 (7)	−0.0033 (7)
C18	0.0301 (9)	0.0309 (10)	0.0320 (9)	−0.0011 (7)	0.0051 (7)	−0.0033 (7)
C19	0.0351 (10)	0.0345 (10)	0.0381 (10)	0.0081 (8)	0.0043 (8)	−0.0079 (8)
C20	0.0435 (11)	0.0239 (9)	0.0393 (11)	0.0051 (8)	−0.0021 (8)	−0.0044 (8)
C21	0.0428 (11)	0.0259 (10)	0.0378 (10)	−0.0047 (8)	0.0047 (8)	0.0006 (8)
C22	0.0287 (9)	0.0255 (9)	0.0300 (9)	−0.0029 (7)	0.0027 (7)	−0.0036 (7)

S1—C8	1.7299 (18)	C7—C8	1.505 (3)
S1—C9	1.7432 (18)	C10—C11	1.397 (3)
O1—C1	1.219 (2)	C10—C15	1.392 (3)
O2—H2	0.8200	C11—H11	0.9300
O2—C22	1.351 (2)	C11—C12	1.381 (3)
N1—C9	1.385 (2)	C12—H12	0.9300
N1—C16	1.290 (2)	C12—C13	1.387 (3)
C1—C2	1.493 (2)	C13—H13	0.9300
C1—C10	1.484 (2)	C13—C14	1.388 (3)
C2—C3	1.431 (2)	C14—H14	0.9300
C2—C9	1.377 (2)	C14—C15	1.386 (3)
C3—C4	1.504 (2)	C15—H15	0.9300
C3—C8	1.361 (3)	C16—H16	0.9300
C4—H4A	0.9700	C16—C17	1.447 (3)
C4—H4B	0.9700	C17—C18	1.409 (3)
C4—C5	1.518 (3)	C17—C22	1.409 (3)
C5—H5A	0.9700	C18—H18	0.9300
C5—H5B	0.9700	C18—C19	1.380 (3)
C5—C6	1.504 (4)	C19—H19	0.9300
C6—H6A	0.9700	C19—C20	1.390 (3)
C6—H6B	0.9700	C20—H20	0.9300
C6—C7	1.523 (3)	C20—C21	1.378 (3)
C7—H7A	0.9700	C21—H21	0.9300
C7—H7B	0.9700	C21—C22	1.395 (3)
C8—S1—C9	91.53 (9)	C2—C9—N1	124.08 (16)
C22—O2—H2	109.5	C11—C10—C1	119.12 (16)
C16—N1—C9	122.47 (15)	C15—C10—C1	121.26 (16)
O1—C1—C2	119.82 (16)	C15—C10—C11	119.53 (17)
O1—C1—C10	121.62 (16)	C10—C11—H11	120.0
C10—C1—C2	118.49 (15)	C12—C11—C10	120.01 (18)
C3—C2—C1	123.18 (15)	C12—C11—H11	120.0
C9—C2—C1	123.70 (16)	C11—C12—H12	119.8
C9—C2—C3	113.09 (16)	C11—C12—C13	120.33 (18)
C2—C3—C4	125.81 (16)	C13—C12—H12	119.8
C8—C3—C2	112.33 (16)	C12—C13—H13	120.0
C8—C3—C4	121.83 (17)	C12—C13—C14	119.94 (18)
C3—C4—H4A	109.6	C14—C13—H13	120.0
C3—C4—H4B	109.6	C13—C14—H14	120.0
C3—C4—C5	110.36 (17)	C15—C14—C13	119.98 (18)
H4A—C4—H4B	108.1	C15—C14—H14	120.0
C5—C4—H4A	109.6	C10—C15—H15	119.9
C5—C4—H4B	109.6	C14—C15—C10	120.19 (17)
C4—C5—H5A	109.2	C14—C15—H15	119.9
C4—C5—H5B	109.2	N1—C16—H16	119.1
H5A—C5—H5B	107.9	N1—C16—C17	121.89 (16)
C6—C5—C4	112.2 (2)	C17—C16—H16	119.1
C6—C5—H5A	109.2	C18—C17—C16	119.34 (17)
C6—C5—H5B	109.2	C22—C17—C16	121.99 (16)
C5—C6—H6A	108.8	C22—C17—C18	118.67 (17)
C5—C6—H6B	108.8	C17—C18—H18	119.7
C5—C6—C7	113.75 (19)	C19—C18—C17	120.70 (18)
H6A—C6—H6B	107.7	C19—C18—H18	119.7
C7—C6—H6A	108.8	C18—C19—H19	120.1
C7—C6—H6B	108.8	C18—C19—C20	119.81 (18)
C6—C7—H7A	109.6	C20—C19—H19	120.1
C6—C7—H7B	109.6	C19—C20—H20	119.7
H7A—C7—H7B	108.2	C21—C20—C19	120.70 (18)
C8—C7—C6	110.05 (17)	C21—C20—H20	119.7
C8—C7—H7A	109.6	C20—C21—H21	119.9
C8—C7—H7B	109.6	C20—C21—C22	120.24 (19)
C3—C8—S1	112.29 (14)	C22—C21—H21	119.9
C3—C8—C7	125.78 (17)	O2—C22—C17	122.26 (17)
C7—C8—S1	121.89 (14)	O2—C22—C21	117.89 (17)
N1—C9—S1	125.12 (13)	C21—C22—C17	119.85 (18)
C2—C9—S1	110.74 (13)
O1—C1—C2—C3	53.9 (2)	C8—C3—C4—C5	−20.5 (3)
O1—C1—C2—C9	−124.32 (19)	C9—S1—C8—C3	−1.22 (14)
O1—C1—C10—C11	18.8 (3)	C9—S1—C8—C7	176.49 (16)
O1—C1—C10—C15	−157.73 (17)	C9—N1—C16—C17	−179.41 (16)
N1—C16—C17—C18	177.77 (17)	C9—C2—C3—C4	−178.91 (16)
N1—C16—C17—C22	−1.6 (3)	C9—C2—C3—C8	−1.2 (2)
C1—C2—C3—C4	2.7 (3)	C10—C1—C2—C3	−123.18 (18)
C1—C2—C3—C8	−179.58 (16)	C10—C1—C2—C9	58.6 (2)
C1—C2—C9—S1	178.63 (13)	C10—C11—C12—C13	1.1 (3)
C1—C2—C9—N1	1.4 (3)	C11—C10—C15—C14	−1.0 (3)
C1—C10—C11—C12	−176.81 (18)	C11—C12—C13—C14	−0.8 (3)
C1—C10—C15—C14	175.54 (17)	C12—C13—C14—C15	−0.4 (3)
C2—C1—C10—C11	−164.18 (16)	C13—C14—C15—C10	1.3 (3)
C2—C1—C10—C15	19.2 (2)	C15—C10—C11—C12	−0.2 (3)
C2—C3—C4—C5	156.98 (18)	C16—N1—C9—S1	−7.9 (3)
C2—C3—C8—S1	1.60 (19)	C16—N1—C9—C2	168.92 (17)
C2—C3—C8—C7	−176.01 (17)	C16—C17—C18—C19	−177.65 (17)
C3—C2—C9—S1	0.30 (19)	C16—C17—C22—O2	−2.3 (3)
C3—C2—C9—N1	−176.90 (16)	C16—C17—C22—C21	177.57 (17)
C3—C4—C5—C6	48.4 (3)	C17—C18—C19—C20	−0.3 (3)
C4—C3—C8—S1	179.39 (13)	C18—C17—C22—O2	178.33 (17)
C4—C3—C8—C7	1.8 (3)	C18—C17—C22—C21	−1.8 (3)
C4—C5—C6—C7	−60.2 (3)	C18—C19—C20—C21	−1.2 (3)
C5—C6—C7—C8	38.5 (3)	C19—C20—C21—C22	1.1 (3)
C6—C7—C8—S1	172.38 (16)	C20—C21—C22—O2	−179.69 (18)
C6—C7—C8—C3	−10.2 (3)	C20—C21—C22—C17	0.4 (3)
C8—S1—C9—N1	177.66 (16)	C22—C17—C18—C19	1.7 (3)
C8—S1—C9—C2	0.50 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.92	2.641 (2)	146
C18—H18···O1i	0.93	2.51	3.436 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.92	2.641 (2)	146
C18—H18⋯O1i	0.93	2.51	3.436 (2)	174

Symmetry code: (i) .