2-(2-Thien­yl)-4,5-dihydro-1H-imidazole. Corrigendum

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809018790

addenda and errata

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page e15

https://doi.org/10.1107/S1600536809018790

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2-(2-Thienyl)-4,5-dihydro-1H-imidazole. Corrigendum

Reza Kia,^a ‡ Hoong-Kun Fun ^a ^*§ and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 5 May 2009; accepted 18 May 2009; online 23 May 2009)

Consideration of a previous unrecognized twinning of the original investigated crystal of the title compound [Kia et al. (2009 ). Acta Cryst. E65, o301] led to improved reliability factors and to a slightly higher precision for all geometric parameters. The crystal under investigation was twinned by pseudo-merohedry with [100, 0 $[\overline{1}]$ 0, 00 $[\overline{1}]$ ] as the twin matrix and a refined twin domain fraction of 0.9610 (5):0.0390 (5). The results of the new crystal structure refinement are given here.

2. Experimental

2.1.1. Crystal data

C₇H₈N₂S
M_r = 152.21
Monoclinic, P 2₁ /c
a = 6.1321 (2) Å
b = 11.5663 (3) Å
c = 10.0098 (3) Å
β = 90.154 (1)°
V = 709.95 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 100 K
0.54 × 0.28 × 0.22 mm

2.1.2. Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.825, T_max = 0.922
28316 measured reflections
3100 independent reflections
3040 reflections with I > 2σ(I)
R_int = 0.021

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.080
S = 1.15
3100 reflections
96 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.857 (16)	2.130 (16)	2.9803 (10)	171.5 (16)
C3—H3A⋯N2ⁱ	0.95	2.59	3.4815 (11)	156
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809018790/wm2233sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809018790/wm2233Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

2-(2-Thienyl)-4,5-dihydro-1H-imidazole top

Crystal data top

C₇H₈N₂S	F(000) = 320
M_r = 152.21	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9869 reflections
a = 6.1321 (2) Å	θ = 2.5–34.3°
b = 11.5663 (3) Å	µ = 0.37 mm⁻¹
c = 10.0098 (3) Å	T = 100 K
β = 90.154 (1)°	Block, colourless
V = 709.95 (4) Å³	0.54 × 0.28 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3100 independent reflections
Radiation source: fine-focus sealed tube	3040 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 35.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.825, T_max = 0.922	k = −18→17
28316 measured reflections	l = −15→15

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0391P)² + 0.2148P] where P = (F_o² + 2F_c²)/3
3100 reflections	(Δ/σ)_max = 0.001
96 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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	0.46976 (3)	0.141639 (18)	0.59512 (2)	0.01527 (6)
N2	0.06708 (11)	0.29657 (6)	0.61145 (7)	0.01355 (11)
N1	0.04589 (11)	0.30384 (6)	0.83752 (7)	0.01323 (11)
C1	0.63940 (14)	0.05379 (8)	0.68566 (9)	0.01780 (15)
H1A	0.7552	0.0101	0.6480	0.021*
C2	0.58842 (14)	0.05399 (7)	0.81867 (9)	0.01659 (14)
H2A	0.6646	0.0100	0.8839	0.020*
C3	0.40890 (13)	0.12729 (7)	0.84861 (8)	0.01337 (13)
H3A	0.3524	0.1382	0.9360	0.016*
C4	0.32621 (12)	0.18073 (6)	0.73587 (7)	0.01149 (12)
C5	0.14267 (12)	0.26046 (6)	0.72548 (7)	0.01079 (11)
C6	−0.15422 (13)	0.36275 (7)	0.79460 (8)	0.01479 (14)
H6A	−0.1723	0.4380	0.8404	0.018*
H6B	−0.2848	0.3144	0.8103	0.018*
C7	−0.11001 (13)	0.37870 (7)	0.64400 (8)	0.01491 (13)
H7A	−0.2425	0.3611	0.5911	0.018*
H7B	−0.0643	0.4591	0.6248	0.018*
H1	0.058 (3)	0.2686 (14)	0.9125 (16)	0.025 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01701 (9)	0.01822 (10)	0.01059 (9)	0.00444 (6)	0.00195 (6)	−0.00027 (6)
N2	0.0150 (3)	0.0168 (3)	0.0088 (2)	0.0027 (2)	−0.0001 (2)	0.0007 (2)
N1	0.0146 (3)	0.0166 (3)	0.0084 (2)	0.0032 (2)	0.0013 (2)	0.0004 (2)
C1	0.0174 (3)	0.0179 (3)	0.0181 (4)	0.0052 (3)	0.0000 (3)	−0.0017 (3)
C2	0.0188 (3)	0.0151 (3)	0.0159 (3)	0.0033 (3)	−0.0028 (3)	0.0004 (2)
C3	0.0164 (3)	0.0128 (3)	0.0109 (3)	0.0005 (2)	−0.0005 (2)	0.0004 (2)
C4	0.0132 (3)	0.0117 (3)	0.0096 (3)	0.0006 (2)	0.0003 (2)	−0.0002 (2)
C5	0.0119 (3)	0.0114 (3)	0.0090 (3)	−0.0006 (2)	0.0006 (2)	−0.0005 (2)
C6	0.0138 (3)	0.0178 (3)	0.0127 (3)	0.0027 (2)	0.0021 (2)	0.0005 (2)
C7	0.0147 (3)	0.0179 (3)	0.0121 (3)	0.0035 (2)	0.0001 (2)	0.0020 (2)

Geometric parameters (Å, º) top

S1—C1	1.7120 (9)	C2—H2A	0.9500
S1—C4	1.7236 (8)	C3—C4	1.3819 (11)
N2—C5	1.2996 (10)	C3—H3A	0.9500
N2—C7	1.4798 (11)	C4—C5	1.4586 (10)
N1—C5	1.3657 (10)	C6—C7	1.5435 (12)
N1—C6	1.4669 (11)	C6—H6A	0.9900
N1—H1	0.858 (16)	C6—H6B	0.9900
C1—C2	1.3684 (13)	C7—H7A	0.9900
C1—H1A	0.9500	C7—H7B	0.9900
C2—C3	1.4221 (12)

C1—S1—C4	91.94 (4)	C5—C4—S1	120.21 (5)
C5—N2—C7	105.85 (6)	N2—C5—N1	116.64 (7)
C5—N1—C6	107.17 (6)	N2—C5—C4	122.62 (7)
C5—N1—H1	120.4 (11)	N1—C5—C4	120.71 (6)
C6—N1—H1	123.3 (11)	N1—C6—C7	101.10 (6)
C2—C1—S1	111.96 (6)	N1—C6—H6A	111.6
C2—C1—H1A	124.0	C7—C6—H6A	111.6
S1—C1—H1A	124.0	N1—C6—H6B	111.6
C1—C2—C3	112.65 (7)	C7—C6—H6B	111.6
C1—C2—H2A	123.7	H6A—C6—H6B	109.4
C3—C2—H2A	123.7	N2—C7—C6	105.62 (6)
C4—C3—C2	112.15 (7)	N2—C7—H7A	110.6
C4—C3—H3A	123.9	C6—C7—H7A	110.6
C2—C3—H3A	123.9	N2—C7—H7B	110.6
C3—C4—C5	128.49 (7)	C6—C7—H7B	110.6
C3—C4—S1	111.29 (6)	H7A—C7—H7B	108.7

C4—S1—C1—C2	0.09 (7)	C6—N1—C5—N2	12.15 (9)
S1—C1—C2—C3	−0.35 (10)	C6—N1—C5—C4	−169.84 (7)
C1—C2—C3—C4	0.50 (11)	C3—C4—C5—N2	−173.20 (8)
C2—C3—C4—C5	179.29 (8)	S1—C4—C5—N2	6.50 (10)
C2—C3—C4—S1	−0.43 (9)	C3—C4—C5—N1	8.92 (12)
C1—S1—C4—C3	0.20 (7)	S1—C4—C5—N1	−171.38 (6)
C1—S1—C4—C5	−179.55 (7)	C5—N1—C6—C7	−17.77 (8)
C7—N2—C5—N1	0.30 (9)	C5—N2—C7—C6	−11.91 (9)
C7—N2—C5—C4	−177.67 (7)	N1—C6—C7—N2	17.89 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.857 (16)	2.130 (16)	2.9803 (10)	171.5 (16)
C3—H3A···N2ⁱ	0.95	2.59	3.4815 (11)	156

Symmetry code: (i) x, −y+1/2, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5471-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Kia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o301. Web of Science CSD CrossRef 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