Crystal structure of 2-amino-N-(2-fluoro-phen-yl)-4,5,6,7-tetra-hydro-1-benzo-thio-phene-3-carboxamide.

In the title compound, C15H15FN2OS, the dihedral angle between the planes of the benzo-thio-phene ring system and the fluoro-benzene ring is 3.74 (14)°. The six-membered ring of the benzo-thio-phene moiety adopts a half-chair conformation. The mol-ecular conformation is consolidated by intra-molecular N-H⋯F and N-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(6) [001] chains.

Related literature

For background to thio­phene derivatives, see: Bonini et al. (2005 ▸); Brault et al. (2005 ▸); Isloor et al. (2010 ▸). For inter­molecular inter­actions involving F atoms, see: Choudhury et al. (2004 ▸).

Experimental

Crystal data

C15H15FN2OS

M = 290.36

Monoclinic

a = 11.213 (13) Å

b = 14.231 (17) Å

c = 9.582 (15) Å

β = 116.76 (3)°

V = 1365 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

5264 measured reflections

2577 independent reflections

2363 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.081

S = 1.84

2577 reflections

182 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▸)

Absolute structure parameter: 0.06 (7)

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: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015018022/hb7493sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018022/hb7493Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015018022/hb7493Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015018022/hb7493fig1.tif

Perspective diagram of the mol­ecule with 50% probability displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S2056989015018022/hb7493fig2.tif

Packing diagram of the mol­ecule viewed down the ’a′ axis.

CCDC reference: 1045467

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

C15H15FN2OS	F(000) = 608
Mr = 290.36	Dx = 1.413 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2577 reflections
a = 11.213 (13) Å	θ = 2.5–26.4°
b = 14.231 (17) Å	µ = 0.25 mm−1
c = 9.582 (15) Å	T = 293 K
β = 116.76 (3)°	Bolck, yellow
V = 1365 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	Rint = 0.029
ω and φ scans	θmax = 26.4°, θmin = 2.5°
5264 measured reflections	h = −13→14
2577 independent reflections	k = −17→17
2363 reflections with I > 2σ(I)	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3
S = 1.84	(Δ/σ)max < 0.001
2577 reflections	Δρmax = 0.20 e Å−3
182 parameters	Δρmin = −0.28 e Å−3
2 restraints	Absolute structure: Flack (1983), ??? Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (7)

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
S14	0.42139 (7)	0.13494 (4)	1.08277 (7)	0.0586 (3)
F7	0.17969 (19)	0.42740 (10)	0.4264 (2)	0.0746 (6)
O10	0.2917 (2)	0.10081 (11)	0.56571 (19)	0.0568 (7)
N8	0.2299 (2)	0.25423 (14)	0.5376 (2)	0.0503 (7)
N16	0.3503 (2)	0.01559 (15)	0.8447 (3)	0.0674 (9)
C1	0.1812 (2)	0.26650 (18)	0.3762 (3)	0.0466 (9)
C2	0.1530 (3)	0.1953 (2)	0.2671 (3)	0.0588 (10)
C3	0.1087 (4)	0.2175 (3)	0.1106 (3)	0.0727 (11)
C4	0.0865 (3)	0.3097 (3)	0.0601 (4)	0.0735 (13)
C5	0.1109 (3)	0.3807 (2)	0.1661 (3)	0.0643 (11)
C6	0.1566 (3)	0.35800 (18)	0.3201 (3)	0.0519 (9)
C9	0.2880 (3)	0.17625 (17)	0.6279 (3)	0.0444 (9)
C11	0.3397 (2)	0.18699 (17)	0.7955 (3)	0.0423 (8)
C12	0.3705 (3)	0.27223 (17)	0.8901 (3)	0.0422 (8)
C13	0.4142 (3)	0.25543 (17)	1.0436 (3)	0.0478 (8)
C15	0.3637 (3)	0.10698 (17)	0.8869 (3)	0.0483 (9)
C17	0.3638 (3)	0.37266 (16)	0.8342 (3)	0.0497 (9)
C18	0.4470 (3)	0.43925 (17)	0.9684 (3)	0.0575 (10)
C19	0.4211 (4)	0.42420 (18)	1.1078 (3)	0.0665 (11)
C20	0.4583 (3)	0.32519 (19)	1.1743 (3)	0.0583 (10)
H2A	0.16370	0.13280	0.29880	0.0710*
H3A	0.09370	0.16960	0.03860	0.0870*
H4A	0.05520	0.32350	−0.04550	0.0880*
H5A	0.09670	0.44300	0.13370	0.0770*
H9A	0.22220	0.30220	0.58740	0.0600*
H15C	0.32330	0.00050	0.74820	0.0810*
H15D	0.36900	−0.02760	0.91420	0.0810*
H18A	0.55430	0.32090	1.23760	0.0700*
H18B	0.41570	0.31140	1.24040	0.0700*
H20A	0.32720	0.43510	1.07740	0.0800*
H20B	0.47240	0.46950	1.18820	0.0800*
H21A	0.54110	0.42920	0.99880	0.0690*
H21B	0.42570	0.50370	0.93290	0.0690*
H22A	0.27150	0.39340	0.78560	0.0600*
H22B	0.39610	0.37500	0.75590	0.0600*

	U11	U22	U33	U12	U13	U23
S14	0.0914 (6)	0.0458 (4)	0.0421 (4)	0.0089 (4)	0.0332 (4)	0.0085 (3)
F7	0.1052 (14)	0.0470 (9)	0.0552 (10)	−0.0004 (8)	0.0217 (9)	−0.0020 (7)
O10	0.0853 (14)	0.0416 (10)	0.0432 (10)	0.0028 (9)	0.0286 (10)	−0.0026 (8)
N8	0.0726 (15)	0.0413 (11)	0.0362 (11)	0.0066 (10)	0.0239 (11)	−0.0015 (8)
N16	0.116 (2)	0.0397 (13)	0.0496 (13)	0.0007 (12)	0.0400 (13)	0.0038 (10)
C1	0.0467 (15)	0.0481 (16)	0.0397 (15)	0.0014 (11)	0.0147 (13)	0.0030 (11)
C2	0.073 (2)	0.0556 (17)	0.0419 (15)	0.0064 (14)	0.0206 (15)	0.0020 (12)
C3	0.087 (2)	0.080 (2)	0.0370 (15)	0.0112 (17)	0.0154 (15)	−0.0070 (15)
C4	0.095 (3)	0.083 (2)	0.0342 (15)	0.0095 (19)	0.0217 (16)	0.0113 (14)
C5	0.070 (2)	0.0614 (18)	0.0486 (18)	0.0004 (14)	0.0153 (15)	0.0137 (13)
C6	0.0546 (17)	0.0487 (16)	0.0459 (16)	−0.0034 (12)	0.0170 (13)	−0.0001 (12)
C9	0.0539 (17)	0.0385 (13)	0.0445 (14)	−0.0016 (12)	0.0255 (13)	0.0000 (11)
C11	0.0541 (17)	0.0391 (13)	0.0377 (13)	0.0027 (11)	0.0241 (13)	0.0029 (10)
C12	0.0534 (16)	0.0389 (13)	0.0379 (15)	0.0012 (11)	0.0238 (13)	0.0015 (10)
C13	0.0616 (16)	0.0414 (13)	0.0426 (15)	0.0068 (12)	0.0255 (14)	0.0037 (10)
C15	0.0671 (19)	0.0425 (14)	0.0408 (15)	0.0012 (12)	0.0293 (14)	0.0005 (11)
C17	0.0697 (17)	0.0404 (14)	0.0431 (13)	0.0014 (12)	0.0291 (12)	0.0014 (10)
C18	0.075 (2)	0.0433 (14)	0.0542 (16)	−0.0033 (13)	0.0292 (15)	−0.0045 (12)
C19	0.100 (2)	0.0474 (15)	0.059 (2)	0.0027 (16)	0.0418 (19)	−0.0082 (14)
C20	0.079 (2)	0.0536 (16)	0.0434 (16)	0.0055 (14)	0.0286 (15)	−0.0018 (12)

S14—C13	1.749 (4)	C12—C17	1.516 (4)
S14—C15	1.734 (4)	C12—C13	1.346 (4)
F7—C6	1.357 (4)	C13—C20	1.497 (4)
O10—C9	1.238 (4)	C17—C18	1.530 (4)
N8—C1	1.400 (4)	C18—C19	1.505 (5)
N8—C9	1.377 (4)	C19—C20	1.525 (4)
N16—C15	1.350 (4)	C2—H2A	0.9300
N8—H9A	0.8600	C3—H3A	0.9300
N16—H15C	0.8600	C4—H4A	0.9300
N16—H15D	0.8600	C5—H5A	0.9300
C1—C6	1.388 (4)	C17—H22A	0.9700
C1—C2	1.386 (4)	C17—H22B	0.9700
C2—C3	1.387 (4)	C18—H21A	0.9700
C3—C4	1.382 (6)	C18—H21B	0.9700
C4—C5	1.370 (5)	C19—H20A	0.9700
C5—C6	1.365 (4)	C19—H20B	0.9700
C9—C11	1.449 (4)	C20—H18A	0.9700
C11—C12	1.460 (4)	C20—H18B	0.9700
C11—C15	1.387 (4)
C13—S14—C15	91.95 (12)	C12—C17—C18	111.9 (2)
C1—N8—C9	129.3 (2)	C17—C18—C19	111.7 (3)
C9—N8—H9A	115.00	C18—C19—C20	112.1 (3)
C1—N8—H9A	115.00	C13—C20—C19	109.8 (2)
H15C—N16—H15D	120.00	C1—C2—H2A	120.00
C15—N16—H15D	120.00	C3—C2—H2A	120.00
C15—N16—H15C	120.00	C2—C3—H3A	119.00
C2—C1—C6	117.1 (2)	C4—C3—H3A	120.00
N8—C1—C2	125.8 (2)	C3—C4—H4A	120.00
N8—C1—C6	117.1 (2)	C5—C4—H4A	120.00
C1—C2—C3	119.9 (3)	C4—C5—H5A	121.00
C2—C3—C4	121.0 (3)	C6—C5—H5A	121.00
C3—C4—C5	119.8 (3)	C12—C17—H22A	109.00
C4—C5—C6	118.6 (3)	C12—C17—H22B	109.00
F7—C6—C5	119.4 (2)	C18—C17—H22A	109.00
C1—C6—C5	123.6 (2)	C18—C17—H22B	109.00
F7—C6—C1	117.0 (2)	H22A—C17—H22B	108.00
N8—C9—C11	116.8 (2)	C17—C18—H21A	109.00
O10—C9—N8	120.4 (2)	C17—C18—H21B	109.00
O10—C9—C11	122.8 (2)	C19—C18—H21A	109.00
C9—C11—C12	129.8 (2)	C19—C18—H21B	109.00
C9—C11—C15	118.7 (2)	H21A—C18—H21B	108.00
C12—C11—C15	111.5 (2)	C18—C19—H20A	109.00
C11—C12—C13	113.5 (2)	C18—C19—H20B	109.00
C13—C12—C17	119.3 (2)	C20—C19—H20A	109.00
C11—C12—C17	127.1 (2)	C20—C19—H20B	109.00
S14—C13—C20	120.30 (19)	H20A—C19—H20B	108.00
C12—C13—C20	128.1 (2)	C13—C20—H18A	110.00
S14—C13—C12	111.56 (19)	C13—C20—H18B	110.00
S14—C15—C11	111.52 (19)	C19—C20—H18A	110.00
N16—C15—C11	129.6 (2)	C19—C20—H18B	110.00
S14—C15—N16	118.8 (2)	H18A—C20—H18B	108.00
C15—S14—C13—C12	−0.1 (3)	N8—C9—C11—C12	−16.9 (5)
C15—S14—C13—C20	−178.1 (3)	N8—C9—C11—C15	161.9 (3)
C13—S14—C15—N16	178.9 (3)	C9—C11—C12—C13	178.4 (3)
C13—S14—C15—C11	−0.1 (3)	C9—C11—C12—C17	−4.5 (6)
C9—N8—C1—C2	16.1 (5)	C15—C11—C12—C13	−0.4 (4)
C9—N8—C1—C6	−165.1 (3)	C15—C11—C12—C17	176.8 (3)
C1—N8—C9—O10	−7.0 (5)	C9—C11—C15—S14	−178.6 (2)
C1—N8—C9—C11	174.7 (3)	C9—C11—C15—N16	2.4 (5)
N8—C1—C2—C3	−178.1 (3)	C12—C11—C15—S14	0.3 (4)
C6—C1—C2—C3	3.2 (5)	C12—C11—C15—N16	−178.6 (3)
N8—C1—C6—F7	−1.1 (4)	C11—C12—C13—S14	0.3 (4)
N8—C1—C6—C5	179.0 (3)	C11—C12—C13—C20	178.1 (3)
C2—C1—C6—F7	177.7 (3)	C17—C12—C13—S14	−177.1 (3)
C2—C1—C6—C5	−2.1 (5)	C17—C12—C13—C20	0.7 (6)
C1—C2—C3—C4	−2.8 (6)	C11—C12—C17—C18	−160.2 (3)
C2—C3—C4—C5	1.3 (6)	C13—C12—C17—C18	16.8 (5)
C3—C4—C5—C6	−0.2 (6)	S14—C13—C20—C19	−170.8 (3)
C4—C5—C6—F7	−179.2 (3)	C12—C13—C20—C19	11.5 (5)
C4—C5—C6—C1	0.6 (6)	C12—C17—C18—C19	−47.1 (4)
O10—C9—C11—C12	164.9 (3)	C17—C18—C19—C20	61.4 (4)
O10—C9—C11—C15	−16.4 (5)	C18—C19—C20—C13	−41.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H9A···F7	0.86	2.26	2.643 (5)	107
N16—H15C···O10	0.86	2.16	2.733 (5)	124
N16—H15D···O10i	0.86	2.25	2.986 (6)	143

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N8H9AF7	0.86	2.26	2.643(5)	107
N16H15CO10	0.86	2.16	2.733(5)	124
N16H15DO10i	0.86	2.25	2.986(6)	143

Symmetry code: (i) .