2-[(1,3-Benzodioxol-5-yl­methyl­idene)amino]-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carbonitrile

Asiri, A.M.; Khan, S.A.; Tahir, M.N.

doi:10.1107/S1600536811029564

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2162

doi:10.1107/S1600536811029564

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2-[(1,3-Benzodioxol-5-ylmethylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile

Abdullah M. Asiri,^a,^b Salman A. Khan ^b and M. Nawaz Tahir ^c ^*

^aThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, King Abduaziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 July 2011; accepted 21 July 2011; online 30 July 2011)

The title compound, C₁₇H₁₄N₂O₂S, crystallizes with two roughly planar molecules in the asymmetric unit, in which the dihedral angles between the 1,3-benzodioxole-5-carbaldehyde moiety and the heterocyclic five-membered ring are 3.76 (5) and 5.33 (12)°. In each molecule, a short C—H⋯S contact generates an S(5) ring. In the crystal, pairs of molecules are linked by a weak C—H⋯N interaction, forming dimers.

Related literature

For a related structure, see: Elerman & Elmali, (1998 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₂S
M_r = 310.36
Triclinic, $[P \overline 1]$
a = 10.9450 (3) Å
b = 10.9895 (3) Å
c = 13.5749 (3) Å
α = 99.409 (1)°
β = 109.707 (1)°
γ = 92.854 (1)°
V = 1506.77 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.32 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.947, T_max = 0.962
21604 measured reflections
5331 independent reflections
3812 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.01
5331 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯S1	0.93	2.65	3.081 (2)	109
C25—H25⋯S2	0.93	2.61	3.060 (2)	110
C7—H7A⋯N4ⁱ	0.97	2.62	3.190 (3)	118
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029564/hb6325sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029564/hb6325Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029564/hb6325Isup3.cml

checkCIF report

Comment top

The crystal structures of 2-salicylideneamino-4,5,6,7-tetrahydrobenzo(b) thiophene-3-carbonitrile (Elerman & Elmali, 1998) has been published which is related to the title compound (I, Fig. 1).

The title compound consist of two molecules having different configuration. In one molecule, the ring system of 1,3-benzodioxole-5-carbaldehyde moiety A (C1—C7/O1/O2) and five membered ring B (C9—C12/S1) of 2-amino-4,5,6,7- tetrahydro-1-benzothiophene-3-carbonitrile group are planar with r. m. s. deviations of 0.010 and 0.007 Å, respectively. The dihedral angle between A/B is 3.76 (5)°. In the second molecule, the ring system of 1,3-benzodioxole-5-carbaldehyde moiety C (C18—C24/O3/O4) and five membered ring D (C26—C29/S2) of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3- carbonitrile group are also almost planar with r. m. s. deviation of 0.003 and 0.003 Å, respectively. The dihedral angle between C/D is 5.33 (12)°. There exist intra-molecular H-bonding of C—H···S type completing S(5) ring (Table 1, Fig. 1) motifs (Bernstein et al., 1995) in each molecule. The inter-molecular H-bondings of C—H···N type links the molecules in pair.

Related literature top

For a related structure, see: Elerman & Elmali, (1998). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of 1,3-benzodioxole-5-carbaldehyde (0.50 g, 3.3 mmol) and 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile (0.58 g, 3.3 mmol) in ethanol (15 ml) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol-chloroform mixture (9:1) to give yellow prisms of the title compound (I).

Yield: 80%; m.p. 452–453 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted lines represent the C—H···S short contacts.
	Fig. 2. The partial packing of (I0, which shows that molecules are linked into pairs.

2-[(1,3-Benzodioxol-5-ylmethylidene)amino]-4,5,6,7-tetrahydro-1- benzothiophene-3-carbonitrile top

Crystal data top

C₁₇H₁₄N₂O₂S	Z = 4
M_r = 310.36	F(000) = 648
Triclinic, P1	D_x = 1.368 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9450 (3) Å	Cell parameters from 3812 reflections
b = 10.9895 (3) Å	θ = 3.0–25.3°
c = 13.5749 (3) Å	µ = 0.22 mm⁻¹
α = 99.409 (1)°	T = 296 K
β = 109.707 (1)°	Prism, yellow
γ = 92.854 (1)°	0.32 × 0.23 × 0.20 mm
V = 1506.77 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5331 independent reflections
Radiation source: fine-focus sealed tube	3812 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.1°, θ_min = 3.0°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.947, T_max = 0.962	l = −16→16
21604 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0574P)² + 0.3989P] where P = (F_o² + 2F_c²)/3
5331 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₂S	γ = 92.854 (1)°
M_r = 310.36	V = 1506.77 (7) Å³
Triclinic, P1	Z = 4
a = 10.9450 (3) Å	Mo Kα radiation
b = 10.9895 (3) Å	µ = 0.22 mm⁻¹
c = 13.5749 (3) Å	T = 296 K
α = 99.409 (1)°	0.32 × 0.23 × 0.20 mm
β = 109.707 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5331 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3812 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.962	R_int = 0.030
21604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.01	Δρ_max = 0.47 e Å⁻³
5331 reflections	Δρ_min = −0.19 e Å⁻³
397 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.69931 (6)	0.61842 (6)	0.38319 (5)	0.0608 (3)
O1	0.83134 (17)	−0.08541 (15)	0.34616 (16)	0.0760 (7)
O2	1.04492 (17)	−0.06592 (16)	0.35358 (15)	0.0732 (7)
N1	0.68413 (17)	0.36120 (16)	0.35774 (13)	0.0469 (6)
N2	0.3467 (2)	0.2739 (2)	0.32998 (19)	0.0791 (9)
C1	0.87133 (19)	0.25306 (19)	0.37004 (16)	0.0454 (7)
C2	1.0002 (2)	0.2632 (2)	0.37598 (19)	0.0574 (8)
C3	1.0676 (2)	0.1591 (2)	0.3701 (2)	0.0636 (10)
C4	1.0009 (2)	0.0478 (2)	0.35961 (18)	0.0523 (8)
C5	0.8728 (2)	0.0370 (2)	0.35467 (17)	0.0495 (8)
C6	0.8052 (2)	0.13625 (19)	0.35878 (17)	0.0484 (7)
C7	0.9391 (3)	−0.1520 (2)	0.3461 (2)	0.0698 (10)
C8	0.8065 (2)	0.3644 (2)	0.37473 (17)	0.0489 (8)
C9	0.6260 (2)	0.4690 (2)	0.36425 (16)	0.0463 (7)
C10	0.4990 (2)	0.4719 (2)	0.35984 (16)	0.0465 (7)
C11	0.4612 (2)	0.5942 (2)	0.37466 (16)	0.0490 (8)
C12	0.5596 (2)	0.6817 (2)	0.38799 (18)	0.0552 (8)
C13	0.5532 (3)	0.8189 (2)	0.4071 (2)	0.0745 (10)
C14	0.4109 (3)	0.8429 (3)	0.3783 (3)	0.0969 (14)
C15	0.3357 (3)	0.7633 (3)	0.4195 (3)	0.0927 (12)
C16	0.3315 (2)	0.6258 (2)	0.37836 (19)	0.0625 (9)
C17	0.4154 (2)	0.3617 (2)	0.34364 (18)	0.0553 (9)
S2	0.74553 (6)	0.38875 (6)	−0.09354 (5)	0.0621 (2)
O3	0.33292 (19)	0.99165 (18)	0.05740 (17)	0.0814 (8)
O4	0.51968 (18)	0.97170 (16)	0.19428 (15)	0.0798 (7)
N3	0.71457 (18)	0.58138 (16)	0.05320 (15)	0.0509 (7)
N4	0.9964 (2)	0.5672 (2)	0.29555 (19)	0.0721 (8)
C18	0.5351 (2)	0.7022 (2)	0.00214 (17)	0.0494 (8)
C19	0.5760 (2)	0.7860 (2)	0.09919 (18)	0.0537 (8)
C20	0.5008 (2)	0.8788 (2)	0.10818 (19)	0.0538 (8)
C21	0.3895 (2)	0.8915 (2)	0.0267 (2)	0.0571 (9)
C22	0.3474 (2)	0.8116 (3)	−0.0684 (2)	0.0675 (10)
C23	0.4220 (2)	0.7156 (2)	−0.07933 (19)	0.0620 (9)
C24	0.4140 (3)	1.0438 (3)	0.1634 (3)	0.0790 (11)
C25	0.6096 (2)	0.6012 (2)	−0.01630 (19)	0.0542 (8)
C26	0.7833 (2)	0.48621 (19)	0.02932 (18)	0.0495 (8)
C27	0.8952 (2)	0.45635 (19)	0.10042 (17)	0.0478 (8)
C28	0.9499 (2)	0.35489 (19)	0.05702 (19)	0.0502 (8)
C29	0.8797 (2)	0.3105 (2)	−0.0468 (2)	0.0550 (8)
C30	0.9103 (3)	0.2036 (2)	−0.1155 (2)	0.0675 (10)
C31	1.0462 (3)	0.1722 (3)	−0.0606 (3)	0.0790 (11)
C32	1.0763 (3)	0.1751 (3)	0.0558 (3)	0.0878 (11)
C33	1.0699 (3)	0.3015 (2)	0.1166 (2)	0.0649 (9)
C34	0.9495 (2)	0.5197 (2)	0.2080 (2)	0.0535 (9)
H2	1.04310	0.34134	0.38414	0.0689*
H3	1.15386	0.16599	0.37317	0.0763*
H6	0.71841	0.12736	0.35432	0.0581*
H7A	0.91573	−0.21367	0.28101	0.0838*
H7B	0.96394	−0.19426	0.40615	0.0838*
H8	0.85578	0.44114	0.39070	0.0587*
H13A	0.59244	0.85699	0.36364	0.0894*
H13B	0.60114	0.85481	0.48136	0.0894*
H14A	0.40709	0.92904	0.40645	0.1157*
H14B	0.37063	0.82949	0.30131	0.1157*
H15A	0.24704	0.78525	0.40004	0.1114*
H15B	0.37364	0.77969	0.49667	0.1114*
H16A	0.30649	0.57872	0.42448	0.0750*
H16B	0.26608	0.60265	0.30742	0.0750*
H19	0.65114	0.77860	0.15506	0.0645*
H22	0.27214	0.82079	−0.12347	0.0811*
H23	0.39555	0.65842	−0.14321	0.0744*
H24A	0.36445	1.04391	0.21071	0.0947*
H24B	0.44678	1.12889	0.16768	0.0947*
H25	0.57911	0.54799	−0.08239	0.0650*
H30A	0.90390	0.22530	−0.18334	0.0810*
H30B	0.84742	0.13191	−0.12909	0.0810*
H31A	1.05551	0.09013	−0.09447	0.0950*
H31B	1.10907	0.23096	−0.06945	0.0950*
H32A	1.16308	0.15071	0.08613	0.1056*
H32B	1.01468	0.11488	0.06452	0.1056*
H33A	1.06867	0.29412	0.18647	0.0778*
H33B	1.14680	0.35662	0.12626	0.0778*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0483 (4)	0.0490 (4)	0.0878 (5)	0.0129 (3)	0.0275 (3)	0.0109 (3)
O1	0.0641 (11)	0.0413 (9)	0.1252 (16)	0.0107 (8)	0.0392 (11)	0.0086 (9)
O2	0.0650 (11)	0.0577 (11)	0.1085 (14)	0.0299 (9)	0.0416 (10)	0.0167 (10)
N1	0.0427 (11)	0.0475 (11)	0.0511 (10)	0.0126 (8)	0.0173 (8)	0.0073 (8)
N2	0.0574 (14)	0.0806 (17)	0.0976 (18)	−0.0021 (13)	0.0271 (13)	0.0153 (14)
C1	0.0384 (12)	0.0472 (13)	0.0500 (12)	0.0104 (10)	0.0146 (10)	0.0078 (10)
C2	0.0417 (13)	0.0537 (14)	0.0791 (16)	0.0074 (11)	0.0216 (12)	0.0175 (12)
C3	0.0435 (13)	0.0665 (17)	0.0918 (19)	0.0174 (12)	0.0326 (13)	0.0227 (14)
C4	0.0496 (14)	0.0513 (14)	0.0616 (14)	0.0190 (11)	0.0245 (11)	0.0114 (10)
C5	0.0467 (13)	0.0445 (13)	0.0577 (13)	0.0080 (10)	0.0201 (10)	0.0061 (10)
C6	0.0364 (12)	0.0487 (13)	0.0591 (13)	0.0079 (10)	0.0177 (10)	0.0042 (10)
C7	0.0760 (18)	0.0537 (16)	0.0867 (19)	0.0237 (14)	0.0357 (15)	0.0122 (13)
C8	0.0439 (13)	0.0453 (13)	0.0576 (13)	0.0080 (10)	0.0184 (10)	0.0078 (10)
C9	0.0441 (12)	0.0480 (13)	0.0473 (12)	0.0133 (10)	0.0163 (10)	0.0076 (9)
C10	0.0400 (12)	0.0569 (14)	0.0424 (12)	0.0113 (10)	0.0133 (9)	0.0098 (10)
C11	0.0473 (13)	0.0600 (14)	0.0428 (12)	0.0205 (11)	0.0161 (10)	0.0135 (10)
C12	0.0538 (14)	0.0542 (14)	0.0572 (14)	0.0231 (12)	0.0177 (11)	0.0087 (11)
C13	0.0763 (18)	0.0552 (16)	0.091 (2)	0.0270 (14)	0.0269 (15)	0.0110 (14)
C14	0.098 (2)	0.078 (2)	0.124 (3)	0.0478 (19)	0.044 (2)	0.0229 (19)
C15	0.090 (2)	0.107 (2)	0.109 (2)	0.062 (2)	0.056 (2)	0.037 (2)
C16	0.0521 (14)	0.0878 (19)	0.0579 (14)	0.0340 (13)	0.0246 (12)	0.0233 (13)
C17	0.0413 (13)	0.0661 (17)	0.0595 (14)	0.0121 (12)	0.0177 (11)	0.0127 (12)
S2	0.0629 (4)	0.0661 (4)	0.0598 (4)	0.0201 (3)	0.0237 (3)	0.0105 (3)
O3	0.0814 (13)	0.0794 (13)	0.1002 (15)	0.0480 (11)	0.0408 (12)	0.0329 (11)
O4	0.0764 (12)	0.0626 (11)	0.0894 (13)	0.0246 (9)	0.0205 (10)	−0.0020 (10)
N3	0.0487 (11)	0.0472 (11)	0.0616 (12)	0.0142 (9)	0.0218 (9)	0.0156 (9)
N4	0.0724 (15)	0.0575 (13)	0.0759 (15)	0.0195 (11)	0.0162 (12)	0.0015 (12)
C18	0.0439 (12)	0.0517 (13)	0.0568 (14)	0.0121 (10)	0.0193 (11)	0.0169 (11)
C19	0.0432 (13)	0.0528 (14)	0.0612 (14)	0.0118 (10)	0.0107 (11)	0.0146 (11)
C20	0.0524 (14)	0.0480 (14)	0.0651 (15)	0.0112 (11)	0.0238 (12)	0.0138 (11)
C21	0.0526 (14)	0.0602 (15)	0.0724 (16)	0.0247 (12)	0.0294 (13)	0.0298 (13)
C22	0.0542 (15)	0.091 (2)	0.0639 (16)	0.0314 (14)	0.0168 (13)	0.0347 (15)
C23	0.0585 (15)	0.0761 (17)	0.0515 (14)	0.0202 (13)	0.0156 (12)	0.0165 (12)
C24	0.082 (2)	0.0575 (16)	0.111 (2)	0.0248 (15)	0.0473 (19)	0.0190 (16)
C25	0.0538 (14)	0.0526 (14)	0.0598 (14)	0.0127 (11)	0.0227 (12)	0.0131 (11)
C26	0.0488 (13)	0.0446 (12)	0.0611 (14)	0.0106 (10)	0.0245 (11)	0.0142 (10)
C27	0.0478 (13)	0.0395 (12)	0.0604 (14)	0.0072 (10)	0.0231 (11)	0.0115 (10)
C28	0.0494 (13)	0.0399 (12)	0.0689 (15)	0.0096 (10)	0.0285 (12)	0.0136 (10)
C29	0.0534 (14)	0.0501 (14)	0.0708 (16)	0.0109 (11)	0.0322 (12)	0.0135 (12)
C30	0.0737 (18)	0.0571 (16)	0.0816 (18)	0.0139 (13)	0.0433 (15)	0.0038 (13)
C31	0.079 (2)	0.0586 (17)	0.108 (2)	0.0217 (14)	0.0472 (17)	0.0045 (15)
C32	0.092 (2)	0.0670 (19)	0.108 (2)	0.0414 (16)	0.0351 (19)	0.0173 (16)
C33	0.0605 (16)	0.0533 (15)	0.0854 (18)	0.0226 (12)	0.0276 (14)	0.0168 (13)
C34	0.0497 (14)	0.0388 (13)	0.0737 (18)	0.0139 (10)	0.0222 (12)	0.0117 (12)

Geometric parameters (Å, º) top

S1—C9	1.731 (2)	C8—H8	0.9300
S1—C12	1.728 (2)	C13—H13B	0.9700
S2—C29	1.725 (2)	C13—H13A	0.9700
S2—C26	1.734 (2)	C14—H14B	0.9700
O1—C7	1.419 (4)	C14—H14A	0.9700
O1—C5	1.372 (3)	C15—H15A	0.9700
O2—C4	1.362 (3)	C15—H15B	0.9700
O2—C7	1.424 (4)	C16—H16B	0.9700
O3—C21	1.364 (3)	C16—H16A	0.9700
O3—C24	1.416 (4)	C18—C19	1.396 (3)
O4—C24	1.419 (4)	C18—C23	1.388 (3)
O4—C20	1.370 (3)	C18—C25	1.448 (3)
N1—C9	1.377 (3)	C19—C20	1.358 (3)
N1—C8	1.278 (3)	C20—C21	1.373 (3)
N2—C17	1.143 (3)	C21—C22	1.356 (4)
N3—C26	1.377 (3)	C22—C23	1.385 (4)
N3—C25	1.272 (3)	C26—C27	1.373 (3)
N4—C34	1.144 (3)	C27—C28	1.428 (3)
C1—C2	1.383 (3)	C27—C34	1.418 (3)
C1—C6	1.401 (3)	C28—C29	1.350 (3)
C1—C8	1.448 (3)	C28—C33	1.496 (4)
C2—C3	1.398 (3)	C29—C30	1.501 (4)
C3—C4	1.354 (3)	C30—C31	1.508 (5)
C4—C5	1.379 (3)	C31—C32	1.496 (5)
C5—C6	1.352 (3)	C32—C33	1.513 (4)
C9—C10	1.373 (3)	C19—H19	0.9300
C10—C11	1.429 (3)	C22—H22	0.9300
C10—C17	1.421 (3)	C23—H23	0.9300
C11—C16	1.493 (3)	C24—H24A	0.9700
C11—C12	1.351 (3)	C24—H24B	0.9700
C12—C13	1.497 (3)	C25—H25	0.9300
C13—C14	1.521 (5)	C30—H30A	0.9700
C14—C15	1.468 (5)	C30—H30B	0.9700
C15—C16	1.516 (4)	C31—H31A	0.9700
C2—H2	0.9300	C31—H31B	0.9700
C3—H3	0.9300	C32—H32A	0.9700
C6—H6	0.9300	C32—H32B	0.9700
C7—H7B	0.9700	C33—H33A	0.9700
C7—H7A	0.9700	C33—H33B	0.9700

C9—S1—C12	91.86 (11)	C15—C16—H16A	109.00
C26—S2—C29	92.06 (12)	C15—C16—H16B	109.00
C5—O1—C7	106.22 (19)	C11—C16—H16A	109.00
C4—O2—C7	106.0 (2)	C11—C16—H16B	109.00
C21—O3—C24	105.9 (2)	C19—C18—C23	120.1 (2)
C20—O4—C24	106.0 (2)	C19—C18—C25	121.2 (2)
C8—N1—C9	120.91 (19)	C23—C18—C25	118.7 (2)
C25—N3—C26	120.5 (2)	C18—C19—C20	116.8 (2)
C2—C1—C6	120.0 (2)	O4—C20—C19	128.0 (2)
C6—C1—C8	121.0 (2)	O4—C20—C21	109.5 (2)
C2—C1—C8	119.0 (2)	C19—C20—C21	122.5 (2)
C1—C2—C3	121.8 (2)	O3—C21—C20	110.2 (2)
C2—C3—C4	116.6 (2)	O3—C21—C22	127.8 (2)
C3—C4—C5	122.0 (2)	C20—C21—C22	122.0 (2)
O2—C4—C5	110.2 (2)	C21—C22—C23	116.6 (2)
O2—C4—C3	127.8 (2)	C18—C23—C22	122.0 (2)
O1—C5—C6	128.3 (2)	O3—C24—O4	108.5 (3)
C4—C5—C6	122.4 (2)	N3—C25—C18	123.4 (2)
O1—C5—C4	109.3 (2)	S2—C26—N3	126.02 (17)
C1—C6—C5	117.2 (2)	S2—C26—C27	109.71 (17)
O1—C7—O2	108.25 (18)	N3—C26—C27	124.3 (2)
N1—C8—C1	122.5 (2)	C26—C27—C28	114.1 (2)
S1—C9—C10	110.04 (17)	C26—C27—C34	122.6 (2)
N1—C9—C10	123.4 (2)	C28—C27—C34	123.3 (2)
S1—C9—N1	126.57 (17)	C27—C28—C29	111.8 (2)
C9—C10—C11	114.0 (2)	C27—C28—C33	125.6 (2)
C9—C10—C17	121.9 (2)	C29—C28—C33	122.7 (2)
C11—C10—C17	124.1 (2)	S2—C29—C28	112.36 (18)
C12—C11—C16	122.6 (2)	S2—C29—C30	122.51 (19)
C10—C11—C12	111.6 (2)	C28—C29—C30	125.1 (2)
C10—C11—C16	125.8 (2)	C29—C30—C31	110.0 (2)
S1—C12—C13	122.2 (2)	C30—C31—C32	112.7 (3)
C11—C12—C13	125.3 (2)	C31—C32—C33	113.0 (3)
S1—C12—C11	112.46 (17)	C28—C33—C32	110.2 (2)
C12—C13—C14	108.9 (2)	N4—C34—C27	177.3 (3)
C13—C14—C15	113.2 (3)	C18—C19—H19	122.00
C14—C15—C16	113.7 (3)	C20—C19—H19	122.00
C11—C16—C15	111.1 (2)	C21—C22—H22	122.00
N2—C17—C10	179.1 (3)	C23—C22—H22	122.00
C1—C2—H2	119.00	C18—C23—H23	119.00
C3—C2—H2	119.00	C22—C23—H23	119.00
C4—C3—H3	122.00	O3—C24—H24A	110.00
C2—C3—H3	122.00	O3—C24—H24B	110.00
C1—C6—H6	121.00	O4—C24—H24A	110.00
C5—C6—H6	121.00	O4—C24—H24B	110.00
O1—C7—H7B	110.00	H24A—C24—H24B	108.00
O2—C7—H7A	110.00	N3—C25—H25	118.00
O2—C7—H7B	110.00	C18—C25—H25	118.00
H7A—C7—H7B	108.00	C29—C30—H30A	110.00
O1—C7—H7A	110.00	C29—C30—H30B	110.00
N1—C8—H8	119.00	C31—C30—H30A	110.00
C1—C8—H8	119.00	C31—C30—H30B	110.00
H13A—C13—H13B	108.00	H30A—C30—H30B	108.00
C14—C13—H13A	110.00	C30—C31—H31A	109.00
C14—C13—H13B	110.00	C30—C31—H31B	109.00
C12—C13—H13A	110.00	C32—C31—H31A	109.00
C12—C13—H13B	110.00	C32—C31—H31B	109.00
H14A—C14—H14B	108.00	H31A—C31—H31B	108.00
C13—C14—H14A	109.00	C31—C32—H32A	109.00
C13—C14—H14B	109.00	C31—C32—H32B	109.00
C15—C14—H14A	109.00	C33—C32—H32A	109.00
C15—C14—H14B	109.00	C33—C32—H32B	109.00
C14—C15—H15B	109.00	H32A—C32—H32B	108.00
C16—C15—H15A	109.00	C28—C33—H33A	110.00
C14—C15—H15A	109.00	C28—C33—H33B	110.00
C16—C15—H15B	109.00	C32—C33—H33A	110.00
H15A—C15—H15B	108.00	C32—C33—H33B	110.00
H16A—C16—H16B	108.00	H33A—C33—H33B	108.00

C12—S1—C9—N1	−176.63 (19)	C9—C10—C11—C12	1.2 (3)
C12—S1—C9—C10	1.35 (17)	C17—C10—C11—C16	1.7 (3)
C9—S1—C12—C11	−0.70 (18)	C10—C11—C12—C13	−179.0 (2)
C9—S1—C12—C13	178.2 (2)	C16—C11—C12—S1	178.43 (17)
C26—S2—C29—C30	179.1 (2)	C10—C11—C12—S1	−0.1 (2)
C26—S2—C29—C28	0.38 (19)	C10—C11—C16—C15	167.3 (2)
C29—S2—C26—N3	178.9 (2)	C12—C11—C16—C15	−11.1 (3)
C29—S2—C26—C27	0.14 (18)	C16—C11—C12—C13	−0.4 (4)
C7—O1—C5—C6	−179.5 (2)	C11—C12—C13—C14	−15.8 (3)
C5—O1—C7—O2	−0.7 (2)	S1—C12—C13—C14	165.4 (2)
C7—O1—C5—C4	0.1 (3)	C12—C13—C14—C15	44.9 (4)
C7—O2—C4—C3	178.4 (2)	C13—C14—C15—C16	−60.2 (4)
C7—O2—C4—C5	−0.9 (3)	C14—C15—C16—C11	40.6 (4)
C4—O2—C7—O1	1.0 (2)	C23—C18—C19—C20	−0.3 (3)
C24—O3—C21—C22	179.8 (3)	C25—C18—C19—C20	178.9 (2)
C21—O3—C24—O4	0.0 (3)	C19—C18—C23—C22	0.8 (4)
C24—O3—C21—C20	0.2 (3)	C25—C18—C23—C22	−178.5 (2)
C20—O4—C24—O3	−0.2 (3)	C19—C18—C25—N3	0.6 (4)
C24—O4—C20—C21	0.3 (3)	C23—C18—C25—N3	179.8 (2)
C24—O4—C20—C19	−179.7 (3)	C18—C19—C20—O4	179.9 (2)
C8—N1—C9—C10	−171.7 (2)	C18—C19—C20—C21	−0.1 (4)
C8—N1—C9—S1	6.0 (3)	O4—C20—C21—O3	−0.4 (3)
C9—N1—C8—C1	179.13 (19)	O4—C20—C21—C22	−179.9 (2)
C25—N3—C26—C27	−178.1 (2)	C19—C20—C21—O3	179.7 (2)
C25—N3—C26—S2	3.4 (3)	C19—C20—C21—C22	0.1 (4)
C26—N3—C25—C18	−177.7 (2)	O3—C21—C22—C23	−179.2 (2)
C2—C1—C6—C5	0.3 (3)	C20—C21—C22—C23	0.4 (4)
C8—C1—C2—C3	−178.9 (2)	C21—C22—C23—C18	−0.8 (4)
C6—C1—C2—C3	0.6 (3)	S2—C26—C27—C28	−0.6 (3)
C8—C1—C6—C5	179.8 (2)	S2—C26—C27—C34	−179.41 (18)
C2—C1—C8—N1	171.9 (2)	N3—C26—C27—C28	−179.4 (2)
C6—C1—C8—N1	−7.6 (3)	N3—C26—C27—C34	1.8 (4)
C1—C2—C3—C4	−0.8 (4)	C26—C27—C28—C29	0.9 (3)
C2—C3—C4—C5	0.2 (4)	C26—C27—C28—C33	−179.0 (2)
C2—C3—C4—O2	−179.1 (2)	C34—C27—C28—C29	179.7 (2)
O2—C4—C5—O1	0.5 (3)	C34—C27—C28—C33	−0.2 (4)
O2—C4—C5—C6	−179.9 (2)	C27—C28—C29—S2	−0.8 (3)
C3—C4—C5—O1	−178.9 (2)	C27—C28—C29—C30	−179.5 (2)
C3—C4—C5—C6	0.7 (4)	C33—C28—C29—S2	179.15 (19)
C4—C5—C6—C1	−0.9 (3)	C33—C28—C29—C30	0.4 (4)
O1—C5—C6—C1	178.6 (2)	C27—C28—C33—C32	163.9 (2)
N1—C9—C10—C11	176.37 (18)	C29—C28—C33—C32	−16.0 (4)
N1—C9—C10—C17	−2.7 (3)	S2—C29—C30—C31	168.2 (2)
S1—C9—C10—C17	179.30 (17)	C28—C29—C30—C31	−13.2 (4)
S1—C9—C10—C11	−1.7 (2)	C29—C30—C31—C32	42.1 (3)
C9—C10—C11—C16	−177.3 (2)	C30—C31—C32—C33	−61.1 (4)
C17—C10—C11—C12	−179.8 (2)	C31—C32—C33—C28	45.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···S1	0.93	2.65	3.081 (2)	109
C25—H25···S2	0.93	2.61	3.060 (2)	110
C7—H7A···N4ⁱ	0.97	2.62	3.190 (3)	118

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₂S
M_r	310.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.9450 (3), 10.9895 (3), 13.5749 (3)
α, β, γ (°)	99.409 (1), 109.707 (1), 92.854 (1)
V (Å³)	1506.77 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.32 × 0.23 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	21604, 5331, 3812
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.01
No. of reflections	5331
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···S1	0.93	2.65	3.081 (2)	109
C25—H25···S2	0.93	2.61	3.060 (2)	110
C7—H7A···N4ⁱ	0.97	2.62	3.190 (3)	118

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing the research facilities and for the financial support of this work via grant No. 3–045/430.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Elerman, Y. & Elmali, A. (1998). Acta Cryst. C54, 529–531. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o2162

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

2-[(1,3-Benzodioxol-5-yl­methyl­­idene)amino]-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(1,3-Benzodioxol-5-ylmethylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile